# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_0GPa
_database_code_depnum_ccdc_archive 'CCDC 2336562'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_0GPa            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.326 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT149_AZO_0GPa            
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.07 Degree
RESPONSE: Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree. 
;
_vrf_PLAT911_AZO_0GPa            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        783 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form


_audit_creation_method           'CIF-fill 1.3q (K.Radacki, 2005-22)'
_audit_creation_date             2023-03-15
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   15.223(14)
_cell_length_b                   5.7851(5)
_cell_length_c                   12.174(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.45(7)
_cell_angle_gamma                90
_cell_volume                     990.9(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       100
_cell_measurement_reflns_used    314
_cell_measurement_theta_min      1.9220
_cell_measurement_theta_max      16.9110

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81270
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 Crystals were grown from saturated solution. For data collection the crystal 
 was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         100
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -32.00  32.00   0.50    0.20    --    0.00   0.00   0.00  128
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.0289372486
_diffrn_orient_matrix_UB_12      0.0062451178
_diffrn_orient_matrix_UB_13      0.0171628015
_diffrn_orient_matrix_UB_21      -0.0032722663
_diffrn_orient_matrix_UB_22      0.0112097743
_diffrn_orient_matrix_UB_23      0.0314503225
_diffrn_orient_matrix_UB_31      0.0020367736
_diffrn_orient_matrix_UB_32      -0.0696692206
_diffrn_orient_matrix_UB_33      0.0065888146
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            4002
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.930
_diffrn_reflns_theta_max         21.468
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.185
_diffrn_measured_fraction_theta_full 0.326
_diffrn_reflns_Laue_measured_fraction_max 0.185
_diffrn_reflns_Laue_measured_fraction_full 0.326
_diffrn_reflns_point_group_measured_fraction_max 0.185
_diffrn_reflns_point_group_measured_fraction_full 0.326
_reflns_number_total             4002
_reflns_number_gt                2663
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
The BASF parameter was refined to 29.6%. The anisotropic displacement parameters
of the disordered nitrogen atoms N2A and N2B were restrained to similar 
behaviour using SIMU restraint.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0661P)²+0.0484P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.37(13)
_refine_ls_number_reflns         4002
_refine_ls_number_parameters     139
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1625
_refine_ls_wR_factor_gt          0.1434
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.031
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4888(3) 0.1018(3) 0.5036(2) 0.0476(14) Uani 1 1 d . U . . .
C1 C 0.4324(3) 0.1351(4) 0.5732(3) 0.0442(15) Uani 1 1 d . U . . .
C2 C 0.3858(4) 0.3433(4) 0.5594(3) 0.0548(17) Uani 1 1 d . U . . .
H2 H 0.392256 0.453398 0.507289 0.066 Uiso 1 1 calc R U . . .
C3 C 0.3294(4) 0.3891(4) 0.6228(3) 0.0598(17) Uani 1 1 d . U . . .
H3 H 0.296396 0.528111 0.611489 0.072 Uiso 1 1 calc R U . . .
C4 C 0.3218(4) 0.2289(5) 0.7028(3) 0.0601(19) Uani 1 1 d . U . . .
H4 H 0.284013 0.259620 0.745615 0.072 Uiso 1 1 calc R U . . .
C5 C 0.3708(4) 0.0234(5) 0.7186(3) 0.0544(18) Uani 1 1 d . U . . .
H5 H 0.366403 -0.083211 0.773488 0.065 Uiso 1 1 calc R U . . .
C6 C 0.4262(3) -0.0274(4) 0.6546(3) 0.0480(15) Uani 1 1 d . U . . .
H6 H 0.458650 -0.167038 0.665516 0.058 Uiso 1 1 calc R U . . .
N2A N 0.9708(8) 0.0760(6) 0.9782(9) 0.060(3) Uani 0.85(2) 1 d . U P A 1
N2B N 0.991(4) -0.076(4) 0.957(4) 0.061(4) Uani 0.15(2) 1 d . U P A 2
C7 C 0.9208(5) 0.0470(6) 0.8510(4) 0.062(2) Uani 1 1 d . U . . .
C8 C 0.9283(5) -0.1358(5) 0.7812(4) 0.067(2) Uani 1 1 d . U . . .
H8 H 0.968263 -0.259768 0.815429 0.081 Uiso 1 1 calc R U . . .
C9 C 0.8758(6) -0.1314(6) 0.6609(5) 0.073(2) Uani 1 1 d . U . . .
H9 H 0.880579 -0.253069 0.613515 0.088 Uiso 1 1 calc R U . . .
C10 C 0.8161(5) 0.0526(7) 0.6096(4) 0.072(3) Uani 1 1 d . U . . .
H10 H 0.780318 0.054569 0.528278 0.086 Uiso 1 1 calc R U . . .
C11 C 0.8103(5) 0.2316(6) 0.6802(4) 0.076(2) Uani 1 1 d . U . . .
H11 H 0.771008 0.356912 0.646211 0.091 Uiso 1 1 calc R U . . .
C12 C 0.8613(5) 0.2281(6) 0.7994(4) 0.072(2) Uani 1 1 d . U . . .
H12 H 0.855803 0.349784 0.846278 0.086 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.048(4) 0.0486(11) 0.0487(19) -0.0002(8) 0.022(3) 0.0022(12)
C1 0.043(5) 0.0472(13) 0.043(2) -0.0041(9) 0.017(3) -0.0024(13)
C2 0.061(6) 0.0505(15) 0.055(2) 0.0018(11) 0.025(3) 0.0045(15)
C3 0.058(6) 0.0554(16) 0.069(3) -0.0050(12) 0.027(4) 0.0101(16)
C4 0.055(6) 0.0709(19) 0.064(3) -0.0122(14) 0.032(4) -0.0033(18)
C5 0.052(6) 0.0651(17) 0.050(2) 0.0007(11) 0.024(4) -0.0037(16)
C6 0.047(5) 0.0503(13) 0.048(2) 0.0010(10) 0.019(3) 0.0022(14)
N2A 0.054(8) 0.066(2) 0.059(5) 0.0051(17) 0.021(6) 0.010(2)
N2B 0.054(9) 0.068(6) 0.060(7) 0.005(6) 0.021(9) 0.009(6)
C7 0.050(7) 0.082(2) 0.053(3) 0.0064(15) 0.020(4) -0.009(2)
C8 0.052(7) 0.073(2) 0.075(3) 0.0081(15) 0.022(4) 0.0050(19)
C9 0.061(8) 0.084(2) 0.076(4) -0.0141(18) 0.028(5) -0.004(2)
C10 0.052(9) 0.104(3) 0.056(3) 0.0031(18) 0.016(5) -0.006(3)
C11 0.070(8) 0.085(2) 0.074(3) 0.0157(17) 0.029(5) 0.015(2)
C12 0.077(8) 0.076(2) 0.070(3) 0.0008(16) 0.035(5) 0.005(2)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.239(4) 3_656 ?
N1 C1 1.431(4) . ?
C1 C2 1.375(5) . ?
C1 C6 1.395(3) . ?
C2 C3 1.382(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2A N2A 1.218(17) 3_757 ?
N2A C7 1.451(12) . ?
N2B N2B 1.31(7) 3_757 ?
N2B C7 1.50(5) . ?
C7 C12 1.371(7) . ?
C7 C8 1.388(5) . ?
C8 C9 1.375(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.384(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.359(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 114.5(2) 3_656 . ?
C2 C1 C6 120.4(3) . . ?
C2 C1 N1 116.3(2) . . ?
C6 C1 N1 123.2(3) . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 118.6(3) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
N2A N2A C7 112.3(8) 3_757 . ?
N2B N2B C7 103(4) 3_757 . ?
C12 C7 C8 119.7(5) . . ?
C12 C7 N2A 112.7(3) . . ?
C8 C7 N2A 127.6(5) . . ?
C12 C7 N2B 152.1(12) . . ?
C8 C7 N2B 88.2(12) . . ?
C9 C8 C7 119.2(4) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 119.1(5) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C12 C11 C10 120.7(5) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C7 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -163.9(5) 3_656 . . . ?
N1 N1 C1 C6 18.4(7) 3_656 . . . ?
C6 C1 C2 C3 -2.6(7) . . . . ?
N1 C1 C2 C3 179.6(4) . . . . ?
C1 C2 C3 C4 1.9(7) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
C3 C4 C5 C6 -1.0(7) . . . . ?
C4 C5 C6 C1 0.4(7) . . . . ?
C2 C1 C6 C5 1.4(7) . . . . ?
N1 C1 C6 C5 179.0(4) . . . . ?
N2A N2A C7 C12 -174.3(7) 3_757 . . . ?
N2A N2A C7 C8 5.0(11) 3_757 . . . ?
N2B N2B C7 C12 -9(7) 3_757 . . . ?
N2B N2B C7 C8 172(4) 3_757 . . . ?
C12 C7 C8 C9 0.2(8) . . . . ?
N2A C7 C8 C9 -179.0(5) . . . . ?
N2B C7 C8 C9 179.6(16) . . . . ?
C7 C8 C9 C10 -0.1(8) . . . . ?
C8 C9 C10 C11 0.5(8) . . . . ?
C9 C10 C11 C12 -1.0(8) . . . . ?
C10 C11 C12 C7 1.1(8) . . . . ?
C8 C7 C12 C11 -0.7(8) . . . . ?
N2A C7 C12 C11 178.7(5) . . . . ?
N2B C7 C12 C11 -179(3) . . . . ?


_shelx_res_file                  
;
TITL sample_0004_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 19:27:04 on 23-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  15.223430   5.785131  12.173722  90.0000 112.4470  90.0000
ZERR    4.00   0.013851   0.000487   0.004294   0.0000   0.0743   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
OMIT -7 -1 8
OMIT -1 -4 0
OMIT -4 -6 1
OMIT -3 -5 1
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.03
FMAP 2
PLAN 20
WGHT    0.066100    0.048400
EXTI    0.369549
BASF   0.29648
FVAR      30.03223   0.84918
N1    1    0.488785    0.101779    0.503646    11.00000    0.04837    0.04862 =
         0.04867   -0.00017    0.02189    0.00217
C1    2    0.432361    0.135114    0.573238    11.00000    0.04304    0.04723 =
         0.04289   -0.00412    0.01702   -0.00235
C2    2    0.385783    0.343317    0.559367    11.00000    0.06077    0.05050 =
         0.05526    0.00182    0.02463    0.00455
AFIX  43
H2    3    0.392256    0.453398    0.507289    11.00000   -1.20000
AFIX   0
C3    2    0.329366    0.389100    0.622752    11.00000    0.05777    0.05540 =
         0.06851   -0.00501    0.02673    0.01014
AFIX  43
H3    3    0.296396    0.528111    0.611489    11.00000   -1.20000
AFIX   0
C4    2    0.321842    0.228935    0.702752    11.00000    0.05462    0.07086 =
         0.06370   -0.01224    0.03246   -0.00326
AFIX  43
H4    3    0.284013    0.259620    0.745615    11.00000   -1.20000
AFIX   0
C5    2    0.370755    0.023419    0.718618    11.00000    0.05236    0.06511 =
         0.04959    0.00074    0.02366   -0.00367
AFIX  43
H5    3    0.366403   -0.083211    0.773488    11.00000   -1.20000
AFIX   0
C6    2    0.426156   -0.027384    0.654602    11.00000    0.04672    0.05031 =
         0.04804    0.00097    0.01916    0.00221
AFIX  43
H6    3    0.458650   -0.167038    0.665516    11.00000   -1.20000
AFIX   0
REM SIMU 0.003 C7 > C12
SIMU 0.003 N2A N2B
PART 1 21.
N2A   1    0.970796    0.075985    0.978239    21.00000    0.05423    0.06638 =
         0.05946    0.00512    0.02094    0.00992
PART 2 -21.
N2B   1    0.990747   -0.076289    0.957152   -21.00000    0.05352    0.06797 =
         0.06014    0.00484    0.02059    0.00944
PART 0
C7    2    0.920811    0.046951    0.851034    11.00000    0.04951    0.08229 =
         0.05313    0.00635    0.01992   -0.00853
C8    2    0.928271   -0.135789    0.781218    11.00000    0.05210    0.07332 =
         0.07510    0.00814    0.02219    0.00495
AFIX  43
H8    3    0.968263   -0.259768    0.815429    11.00000   -1.20000
AFIX   0
C9    2    0.875841   -0.131384    0.660872    11.00000    0.06140    0.08380 =
         0.07607   -0.01410    0.02830   -0.00433
AFIX  43
H9    3    0.880579   -0.253069    0.613515    11.00000   -1.20000
AFIX   0
C10   2    0.816075    0.052555    0.609595    11.00000    0.05157    0.10377 =
         0.05570    0.00306    0.01591   -0.00642
AFIX  43
H10   3    0.780318    0.054569    0.528278    11.00000   -1.20000
AFIX   0
C11   2    0.810277    0.231635    0.680192    11.00000    0.07023    0.08528 =
         0.07432    0.01574    0.02919    0.01472
AFIX  43
H11   3    0.771008    0.356912    0.646211    11.00000   -1.20000
AFIX   0
C12   2    0.861306    0.228147    0.799364    11.00000    0.07658    0.07592 =
         0.06953    0.00077    0.03482    0.00485
AFIX  43
H12   3    0.855803    0.349784    0.846278    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0004_bn1 in P2(1)/c
REM wR2 = 0.1625, GooF = S = 1.045, Restrained GooF = 1.033 for all data
REM R1 = 0.0609 for 2663 Fo > 4sig(Fo) and 0.0935 for all 4002 data
REM 139 parameters refined using 96 restraints

END

WGHT      0.0661      0.0484

REM Highest difference peak  0.178,  deepest hole -0.151,  1-sigma level  0.031
Q1    1   0.4332  0.0587  0.6069  11.00000  0.05    0.18
Q2    1   0.4925  0.2096  0.4666  11.00000  0.05    0.13
Q3    1   0.3513  0.3173  0.6789  11.00000  0.05    0.11
Q4    1   0.5286  0.3219  0.6017  11.00000  0.05    0.10
Q5    1   0.1998  0.1165  0.6813  11.00000  0.05    0.10
Q6    1   0.8059  0.5120  0.6724  11.00000  0.05    0.10
Q7    1   0.3496  0.3540  0.5902  11.00000  0.05    0.10
Q8    1   0.8009  0.4701  0.6010  11.00000  0.05    0.09
Q9    1   0.4691 -0.2213  0.8197  11.00000  0.05    0.09
Q10   1   0.9087 -0.2324  0.7302  11.00000  0.05    0.09
Q11   1   0.9384 -0.0673  0.7506  11.00000  0.05    0.09
Q12   1   0.8545  0.3847  0.8893  11.00000  0.05    0.09
Q13   1   0.4422  0.5683  0.5279  11.00000  0.05    0.09
Q14   1   0.8880  0.4530  0.8616  11.00000  0.05    0.09
Q15   1   0.4187  0.5671  0.7240  11.00000  0.05    0.09
Q16   1   0.3587  0.5259  0.7113  11.00000  0.05    0.08
Q17   1   0.8504 -0.3886  0.7285  11.00000  0.05    0.08
Q18   1   0.3989 -0.2326  0.6429  11.00000  0.05    0.08
Q19   1   0.3234  0.5272  0.7274  11.00000  0.05    0.08
Q20   1   0.4031  0.5557  0.5584  11.00000  0.05    0.08
;
_shelx_res_checksum              20288
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_13GPa_HPI
_database_code_depnum_ccdc_archive 'CCDC 2336574'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_13GPa_HPI       
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.473 Why?  
RESPONSE: Data were collected from a single crystal loaded within a diamond
anvil high-pressure cell. A large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT411_AZO_13GPa_HPI       
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.79 Ang.  
RESPONSE: Intermolecular distances are strongly shortened at high 
pressure and atoms approach closer to one another than at ambient 
conditions or low temperature.
;
_vrf_PLAT149_AZO_13GPa_HPI       
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.07 Degree
RESPONSE: Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree.
;
_vrf_PLAT911_AZO_13GPa_HPI       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        633 Report
RESPONSE: Data were collected from a single crystal loaded within a diamond
anvil high-pressure cell. A large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3s (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-16
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   12.452(8)
_cell_length_b                   5.4749(6)
_cell_length_c                   10.723(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.90(7)
_cell_angle_gamma                90
_cell_volume                     663.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       13040000
_cell_measurement_reflns_used    575
_cell_measurement_theta_min      2.3890
_cell_measurement_theta_max      20.7520

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.825
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.42137
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         13040000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    0.50    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0330378983
_diffrn_orient_matrix_UB_12      0.0248477619
_diffrn_orient_matrix_UB_13      -0.0251298246
_diffrn_orient_matrix_UB_21      -0.0119596614
_diffrn_orient_matrix_UB_22      -0.0707165628
_diffrn_orient_matrix_UB_23      -0.0079324668
_diffrn_orient_matrix_UB_31      -0.0089864902
_diffrn_orient_matrix_UB_32      0.0024071679
_diffrn_orient_matrix_UB_33      0.0327004430
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            1562
_diffrn_reflns_av_unetI/netI     0.0713
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.385
_diffrn_reflns_theta_max         20.722
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.285
_diffrn_measured_fraction_theta_full 0.473
_diffrn_reflns_Laue_measured_fraction_max 0.285
_diffrn_reflns_Laue_measured_fraction_full 0.473
_diffrn_reflns_point_group_measured_fraction_max 0.285
_diffrn_reflns_point_group_measured_fraction_full 0.473
_reflns_number_total             1019
_reflns_number_gt                638
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal class for the 
 calculation of statistics and refinement. _reflns_Friedel_fraction is 
 defined as the number of unique Friedel pairs measured divided by the number 
 that would be possible theoretically, ignoring centric projections and 
 systematic absences.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          
;
 Some reflections were removed from refinement as outliers. 
The anisotropic displacement parameters of all atoms were restrained to 
isotropic behqaviour using ISOR restraint.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1199P)²] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1019
_refine_ls_number_parameters     127
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.1857
_refine_ls_wR_factor_gt          0.1727
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.950
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.058
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4903(4) 0.1109(4) 0.5072(3) 0.0286(12) Uani 1 1 d . U . . .
C1 C 0.4252(5) 0.1417(5) 0.5859(4) 0.0282(13) Uani 1 1 d . U . . .
C2 C 0.3795(5) 0.3738(5) 0.5868(4) 0.0294(14) Uani 1 1 d . U . . .
H2 H 0.385809 0.497287 0.530717 0.035 Uiso 1 1 calc R U . . .
C3 C 0.3246(5) 0.4161(5) 0.6732(4) 0.0287(13) Uani 1 1 d . U . . .
H3 H 0.291090 0.567963 0.673112 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3192(5) 0.2355(5) 0.7590(5) 0.0306(14) Uani 1 1 d . U . . .
H4 H 0.283066 0.267038 0.817578 0.037 Uiso 1 1 calc R U . . .
C5 C 0.3666(5) 0.0077(5) 0.7596(5) 0.0281(13) Uani 1 1 d . U . . .
H5 H 0.364955 -0.111723 0.820423 0.034 Uiso 1 1 calc R U . . .
C6 C 0.4163(5) -0.0415(5) 0.6701(5) 0.0292(13) Uani 1 1 d . U . . .
H6 H 0.443896 -0.197711 0.665862 0.035 Uiso 1 1 calc R U . . .
N2 N 0.9857(4) 0.1079(4) 0.9791(4) 0.0308(13) Uani 1 1 d . U . . .
C7 C 0.9221(5) 0.1217(5) 0.8363(5) 0.0279(13) Uani 1 1 d . U . . .
C8 C 0.9145(5) -0.0719(5) 0.7483(5) 0.0290(13) Uani 1 1 d . U . . .
H8 H 0.944191 -0.225033 0.783563 0.035 Uiso 1 1 calc R U . . .
C9 C 0.8624(6) -0.0329(5) 0.6085(5) 0.0295(13) Uani 1 1 d . U . . .
H9 H 0.858853 -0.158017 0.548194 0.035 Uiso 1 1 calc R U . . .
C10 C 0.8156(5) 0.1932(5) 0.5589(5) 0.0331(14) Uani 1 1 d . U . . .
H10 H 0.778123 0.218332 0.464399 0.040 Uiso 1 1 calc R U . . .
C11 C 0.8233(5) 0.3830(5) 0.6464(5) 0.0308(13) Uani 1 1 d . U . . .
H11 H 0.792895 0.535454 0.610725 0.037 Uiso 1 1 calc R U . . .
C12 C 0.8752(5) 0.3485(5) 0.7854(5) 0.0292(13) Uani 1 1 d . U . . .
H12 H 0.879064 0.475338 0.844771 0.035 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.035(4) 0.0283(12) 0.029(2) -0.0011(9) 0.020(3) 0.0003(12)
C1 0.033(4) 0.0264(13) 0.035(2) -0.0017(11) 0.024(3) -0.0008(13)
C2 0.036(4) 0.0262(13) 0.034(2) -0.0007(11) 0.023(3) -0.0002(13)
C3 0.031(4) 0.0261(13) 0.034(2) 0.0003(11) 0.019(3) 0.0027(14)
C4 0.032(4) 0.0304(14) 0.039(3) -0.0020(12) 0.024(3) -0.0005(14)
C5 0.030(4) 0.0268(13) 0.034(2) 0.0004(11) 0.019(3) -0.0012(13)
C6 0.035(4) 0.0245(13) 0.037(2) 0.0008(11) 0.024(3) 0.0018(13)
N2 0.036(4) 0.0285(12) 0.035(2) 0.0033(10) 0.022(3) 0.0019(12)
C7 0.028(4) 0.0308(14) 0.031(2) 0.0026(12) 0.018(3) -0.0015(13)
C8 0.030(4) 0.0253(13) 0.037(3) 0.0012(12) 0.020(3) -0.0009(14)
C9 0.029(4) 0.0289(14) 0.038(2) -0.0029(12) 0.022(3) -0.0035(14)
C10 0.032(4) 0.0338(15) 0.041(3) 0.0007(13) 0.023(3) -0.0034(15)
C11 0.033(4) 0.0285(13) 0.038(2) 0.0021(12) 0.022(3) -0.0002(14)
C12 0.029(4) 0.0269(14) 0.038(2) -0.0008(12) 0.021(3) -0.0014(14)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.260(5) 3_656 ?
N1 C1 1.406(4) . ?
C1 C6 1.385(4) . ?
C1 C2 1.394(4) . ?
C2 C3 1.383(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.261(5) 3_757 ?
N2 C7 1.399(6) . ?
C7 C12 1.382(5) . ?
C7 C8 1.396(5) . ?
C8 C9 1.376(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.376(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.364(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 112.2(3) 3_656 . ?
C6 C1 C2 120.7(3) . . ?
C6 C1 N1 122.0(3) . . ?
C2 C1 N1 117.0(2) . . ?
C3 C2 C1 118.4(3) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 119.6(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 119.9(3) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N2 N2 C7 112.6(4) 3_757 . ?
C12 C7 C8 121.2(4) . . ?
C12 C7 N2 115.5(3) . . ?
C8 C7 N2 123.0(4) . . ?
C9 C8 C7 119.0(3) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 119.3(3) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 121.3(4) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C7 118.9(3) . . ?
C11 C12 H12 120.6 . . ?
C7 C12 H12 120.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C6 18.2(9) 3_656 . . . ?
N1 N1 C1 C2 -168.2(5) 3_656 . . . ?
C6 C1 C2 C3 -0.3(8) . . . . ?
N1 C1 C2 C3 -174.1(5) . . . . ?
C1 C2 C3 C4 2.2(8) . . . . ?
C2 C3 C4 C5 -1.0(9) . . . . ?
C3 C4 C5 C6 -2.2(9) . . . . ?
C4 C5 C6 C1 4.1(9) . . . . ?
C2 C1 C6 C5 -2.8(9) . . . . ?
N1 C1 C6 C5 170.6(5) . . . . ?
N2 N2 C7 C12 172.2(4) 3_757 . . . ?
N2 N2 C7 C8 -13.5(7) 3_757 . . . ?
C12 C7 C8 C9 1.9(7) . . . . ?
N2 C7 C8 C9 -172.1(4) . . . . ?
C7 C8 C9 C10 -2.2(8) . . . . ?
C8 C9 C10 C11 2.1(7) . . . . ?
C9 C10 C11 C12 -1.7(7) . . . . ?
C10 C11 C12 C7 1.4(8) . . . . ?
C8 C7 C12 C11 -1.5(7) . . . . ?
N2 C7 C12 C11 172.9(4) . . . . ?


_shelx_res_file                  
;
TITL sample_0118_crystal1_bn2 in P2(1)/n
    sample_0118_crystal1_bn2.res
    created by SHELXL-2018/3 at 10:21:52 on 27-Feb-2023
REM P2(1)/n (#14 with fixed user cell!)
CELL 0.41000  12.451719   5.474919  10.722598  90.0000 114.9027  90.0000
ZERR    4.00   0.008216   0.000649   0.004353   0.0000   0.0667   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
OMIT -9 4 9
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.119900
FVAR      13.03156
N1    1    0.490325    0.110856    0.507216    11.00000    0.03523    0.02828 =
         0.02885   -0.00106    0.01990    0.00031
C1    2    0.425188    0.141666    0.585949    11.00000    0.03269    0.02642 =
         0.03543   -0.00171    0.02397   -0.00085
C2    2    0.379500    0.373848    0.586843    11.00000    0.03570    0.02618 =
         0.03445   -0.00068    0.02273   -0.00024
AFIX  43
H2    3    0.385809    0.497287    0.530717    11.00000   -1.20000
AFIX   0
C3    2    0.324586    0.416100    0.673206    11.00000    0.03087    0.02608 =
         0.03433    0.00032    0.01893    0.00267
AFIX  43
H3    3    0.291090    0.567963    0.673112    11.00000   -1.20000
AFIX   0
C4    2    0.319207    0.235464    0.759003    11.00000    0.03191    0.03040 =
         0.03862   -0.00204    0.02372   -0.00048
AFIX  43
H4    3    0.283066    0.267038    0.817578    11.00000   -1.20000
AFIX   0
C5    2    0.366644    0.007718    0.759604    11.00000    0.03000    0.02682 =
         0.03379    0.00036    0.01948   -0.00123
AFIX  43
H5    3    0.364955   -0.111723    0.820423    11.00000   -1.20000
AFIX   0
C6    2    0.416253   -0.041534    0.670116    11.00000    0.03480    0.02454 =
         0.03709    0.00077    0.02370    0.00177
AFIX  43
H6    3    0.443896   -0.197711    0.665862    11.00000   -1.20000
AFIX   0
N2    1    0.985743    0.107945    0.979119    11.00000    0.03611    0.02855 =
         0.03505    0.00330    0.02203    0.00190
C7    2    0.922090    0.121746    0.836271    11.00000    0.02850    0.03077 =
         0.03051    0.00256    0.01837   -0.00151
C8    2    0.914493   -0.071915    0.748262    11.00000    0.03035    0.02534 =
         0.03737    0.00120    0.02019   -0.00094
AFIX  43
H8    3    0.944191   -0.225033    0.783563    11.00000   -1.20000
AFIX   0
C9    2    0.862405   -0.032915    0.608483    11.00000    0.02947    0.02894 =
         0.03825   -0.00286    0.02229   -0.00348
AFIX  43
H9    3    0.858853   -0.158017    0.548194    11.00000   -1.20000
AFIX   0
C10   2    0.815625    0.193245    0.558882    11.00000    0.03234    0.03378 =
         0.04080    0.00070    0.02289   -0.00336
AFIX  43
H10   3    0.778123    0.218332    0.464399    11.00000   -1.20000
AFIX   0
C11   2    0.823288    0.382956    0.646438    11.00000    0.03341    0.02848 =
         0.03772    0.00206    0.02202   -0.00025
AFIX  43
H11   3    0.792895    0.535454    0.610725    11.00000   -1.20000
AFIX   0
C12   2    0.875236    0.348491    0.785354    11.00000    0.02949    0.02694 =
         0.03809   -0.00077    0.02098   -0.00135
AFIX  43
H12   3    0.879064    0.475338    0.844771    11.00000   -1.20000
AFIX   0
HKLF 4




REM  sample_0118_crystal1_bn2 in P2(1)/n
REM wR2 = 0.1857, GooF = S = 0.954, Restrained GooF = 0.950 for all data
REM R1 = 0.0684 for 638 Fo > 4sig(Fo) and 0.0987 for all 1019 data
REM 127 parameters refined using 84 restraints

END

WGHT      0.1199      0.0000

REM Highest difference peak  0.232,  deepest hole -0.240,  1-sigma level  0.058
Q1    1   0.8354 -0.0659  0.6688  11.00000  0.05    0.23
Q2    1   0.9084  0.0237  0.7932  11.00000  0.05    0.23
Q3    1   0.7261  0.3796  0.5548  11.00000  0.05    0.23
Q4    1   0.4022  0.4089  0.7605  11.00000  0.05    0.22
Q5    1   0.5035  0.2225  0.4714  11.00000  0.05    0.21
Q6    1   0.4165  0.0511  0.6272  11.00000  0.05    0.20
Q7    1   0.5424 -0.0966  0.7239  11.00000  0.05    0.20
Q8    1   0.3351  0.1426  0.5020  11.00000  0.05    0.20
Q9    1   0.3931  0.5647  0.7327  11.00000  0.05    0.19
Q10   1   0.7907  0.3522  0.6929  11.00000  0.05    0.19
Q11   1   0.4306  0.2388  0.8756  11.00000  0.05    0.18
Q12   1   0.3358 -0.0772  0.5855  11.00000  0.05    0.18
Q13   1   0.9098 -0.0202  0.6917  11.00000  0.05    0.18
Q14   1   0.4078  0.2537  0.5722  11.00000  0.05    0.18
Q15   1   0.8284  0.4416  0.9005  11.00000  0.05    0.18
Q16   1   0.9530  0.2688  1.0116  11.00000  0.05    0.18
Q17   1   0.3812  0.4038  0.6537  11.00000  0.05    0.17
Q18   1   0.3310 -0.1317  0.8604  11.00000  0.05    0.17
Q19   1   0.9618  0.1183  0.8884  11.00000  0.05    0.17
Q20   1   0.8127  0.2941  0.5961  11.00000  0.05    0.17
;
_shelx_res_checksum              35130
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_100K
_database_code_depnum_ccdc_archive 'CCDC 2336566'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;
_audit_creation_date             2021-08-06
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_common            ?
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.9840(4)
_cell_length_b                   5.69830(10)
_cell_length_c                   12.0341(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.452(3)
_cell_angle_gamma                90
_cell_volume                     949.63(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6726
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.5080
_cell_measurement_theta_min      3.1830
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.885
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.827
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Numerical
absorption correction based on gaussian integration over a 
multifaceted crystal model Empirical absorption correction using 
spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0080
-1 0 0 0.0331
0 -1 0 0.0743
0 1 0 0.0913
-4 0 5 0.0433
5 3 -5 0.0630
4 1 -5 0.0475

_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.041
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0000 -0.0000 0.0000 -0.0167 -0.1079 -0.0214
-1.0000 0.0000 -0.0000 0.0167 0.1079 0.0214
-0.0000 -1.0000 0.0000 -0.2641 0.0311 0.0490
0.0000 1.0000 -0.0000 0.2641 -0.0311 -0.0490
-4.0000 0.0000 5.0000 0.1249 0.0372 0.6517
5.0000 3.0000 -5.0000 0.6508 -0.2383 -0.8199
4.0000 1.0000 -5.0000 0.1392 -0.0682 -0.7006

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10160
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.476
_diffrn_reflns_theta_min         3.191
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     75.00 131.00   0.50    0.05    --   85.25  22.00-144.75  112
  2  ω     87.00 132.00   0.50    0.05    --   82.37  15.00 -90.00   90
  3  ω     60.00 132.00   0.50    0.05    --   82.37  15.00 120.00  144
  4  ω     98.00 134.00   0.50    0.05    --   85.25 122.00  94.09   72
  5  ω     48.00  73.00   0.50    0.05    --   85.25 -84.00-114.47   50
  6  ω     73.00  99.00   0.50    0.05    --   85.25-138.00-132.97   52
  7  ω     34.00 100.00   0.50    0.05    --   82.37-114.00 -52.00  132
  8  ω     12.00  81.00   0.50    0.05    --   58.71-114.00 -52.00  138
  9  ω     23.00  93.00   0.50    0.05    --   71.33-114.00 -52.00  140
 10  ω     53.00 100.00   0.50    0.05    --   85.25-112.00   7.03   94
 11  ω     39.00 100.00   0.50    0.05    --   82.37-112.00  30.00  122
 12  ω     55.00  99.00   0.50    0.05    --   82.37-112.00  60.00   88
 13  ω     47.00  97.00   0.50    0.05    --   85.25-129.00 170.19  100
 14  ω     40.00  65.00   0.50    0.05    --   82.37 -95.00 150.00   50
 15  ω     43.00  81.00   0.50    0.05    --   82.37-112.00 120.00   76
 16  ω     39.00  65.00   0.50    0.05    --   85.25-109.00-172.69   52
 17  ω     44.00  85.00   0.50    0.05    --   85.25-101.00-115.07   82
 18  ω     41.00  89.00   0.50    0.05    --   85.25-108.00 -39.72   96
 19  ω    -33.00  -7.00   0.50    0.05    --  -10.00 115.00 107.70   52
 20  ω    -82.00 -12.00   0.50    0.05    --  -60.25 114.00  38.00  140
 21  ω    -92.00 -21.00   0.50    0.05    --  -69.78 114.00  38.00  142
 22  ω    -98.00 -28.00   0.50    0.05    --  -76.33 114.00  38.00  140
 23  ω   -124.00 -95.00   0.50    0.05    --  -79.50 -65.00  16.03   58
 24  ω   -106.00 -71.00   0.50    0.05    --  -58.00 -51.00 -39.80   70
 25  ω   -123.00 -88.00   0.50    0.05    --  -74.00 -47.00 -57.92   70
 26  ω   -129.00 -92.00   0.50    0.05    --  -79.50 -45.00 -86.23   74
 27  ω   -116.00 -79.00   0.50    0.05    --  -66.00 -45.00   0.45   74
 28  ω   -126.00 -92.00   0.50    0.05    --  -79.50 -57.00 178.65   68
 29  ω   -128.00 -93.00   0.50    0.05    --  -79.50 -50.00 125.24   70
 30  ω   -127.00 -99.00   0.50    0.05    --  -79.50-110.00 -84.21   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0166850000
_diffrn_orient_matrix_UB_12      0.2641430000
_diffrn_orient_matrix_UB_13      0.0116398000
_diffrn_orient_matrix_UB_21      -0.1079206000
_diffrn_orient_matrix_UB_22      -0.0310851000
_diffrn_orient_matrix_UB_23      -0.0789037000
_diffrn_orient_matrix_UB_31      -0.0213918000
_diffrn_orient_matrix_UB_32      -0.0489608000
_diffrn_orient_matrix_UB_33      0.1132176000
_diffrn_oxdiff_digest_frames     
;
01824503bce61dfe1cb41afd55941c155e0270408fd
;
_diffrn_oxdiff_digest_hkl        
;
0139d209c9f97b4e294c0951eb1ea7403065e0
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1759
_reflns_number_total             1920
_reflns_odcompleteness_completeness 98.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0045(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         1920
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²+0.3792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0856
_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of 
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement. R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger.
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   iterative
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.49018(6) 0.10564(16) 0.50521(8) 0.0171(2) Uani 1 1 d . . . . .
C1 C 0.43303(7) 0.13833(18) 0.57578(9) 0.0159(2) Uani 1 1 d . . . . .
C2 C 0.38571(8) 0.35341(19) 0.56199(9) 0.0185(2) Uani 1 1 d . . . . .
C3 C 0.32804(8) 0.3991(2) 0.62657(10) 0.0202(2) Uani 1 1 d . . . . .
C4 C 0.32064(8) 0.2347(2) 0.70809(9) 0.0201(2) Uani 1 1 d . . . . .
C5 C 0.37073(7) 0.0233(2) 0.72426(9) 0.0189(2) Uani 1 1 d . . . . .
C6 C 0.42629(7) -0.02723(19) 0.65779(9) 0.0169(2) Uani 1 1 d . . . . .
H2 H 0.3937(9) 0.470(2) 0.5061(12) 0.022(3) Uiso 1 1 d . . . . .
H3 H 0.2940(9) 0.550(3) 0.6145(11) 0.022(3) Uiso 1 1 d . . . . .
H4 H 0.2814(9) 0.267(2) 0.7559(11) 0.022(3) Uiso 1 1 d . . . . .
H5 H 0.3677(9) -0.095(2) 0.7855(12) 0.024(3) Uiso 1 1 d . . . . .
H6 H 0.4609(9) -0.172(2) 0.6677(10) 0.016(3) Uiso 1 1 d . . . . .
N2 N 0.96766(7) 0.07400(17) 0.97669(8) 0.0227(2) Uani 1 1 d . . . . .
C7 C 0.91878(7) 0.0478(2) 0.84906(9) 0.0200(2) Uani 1 1 d . . . . .
C8 C 0.92964(8) -0.1436(2) 0.78270(10) 0.0216(3) Uani 1 1 d . . . . .
C9 C 0.87750(8) -0.1479(2) 0.65917(10) 0.0230(3) Uani 1 1 d . . . . .
C10 C 0.81641(8) 0.0369(2) 0.60233(10) 0.0229(3) Uani 1 1 d . . . . .
C11 C 0.80641(8) 0.2263(2) 0.66887(10) 0.0239(3) Uani 1 1 d . . . . .
C12 C 0.85723(8) 0.2314(2) 0.79266(10) 0.0224(3) Uani 1 1 d . . . . .
H8 H 0.9733(10) -0.271(3) 0.8231(12) 0.026(3) Uiso 1 1 d . . . . .
H9 H 0.8838(10) -0.282(3) 0.6116(13) 0.030(4) Uiso 1 1 d . . . . .
H10 H 0.7794(10) 0.034(2) 0.5161(13) 0.027(3) Uiso 1 1 d . . . . .
H11 H 0.7633(10) 0.358(3) 0.6293(13) 0.032(4) Uiso 1 1 d . . . . .
H12 H 0.8508(10) 0.365(3) 0.8429(12) 0.029(4) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0176(4) 0.0177(4) 0.0165(4) -0.0001(3) 0.0069(3) 0.0011(3)
C1 0.0148(5) 0.0174(5) 0.0147(5) -0.0024(4) 0.0048(4) -0.0012(4)
C2 0.0195(5) 0.0174(5) 0.0179(5) 0.0001(4) 0.0063(4) -0.0004(4)
C3 0.0191(5) 0.0184(5) 0.0224(5) -0.0029(4) 0.0071(4) 0.0020(4)
C4 0.0171(5) 0.0244(6) 0.0201(5) -0.0049(4) 0.0085(4) -0.0017(4)
C5 0.0186(5) 0.0213(6) 0.0166(5) -0.0003(4) 0.0064(4) -0.0031(4)
C6 0.0161(5) 0.0164(5) 0.0168(5) -0.0009(4) 0.0047(4) 0.0000(4)
N2 0.0216(5) 0.0243(5) 0.0218(5) 0.0012(4) 0.0078(4) 0.0019(4)
C7 0.0164(5) 0.0257(6) 0.0189(5) 0.0015(4) 0.0077(4) -0.0026(4)
C8 0.0166(5) 0.0239(6) 0.0242(5) 0.0028(5) 0.0076(4) 0.0008(4)
C9 0.0197(5) 0.0266(6) 0.0242(5) -0.0044(5) 0.0101(4) -0.0034(5)
C10 0.0173(5) 0.0331(6) 0.0174(5) 0.0010(5) 0.0057(4) -0.0031(5)
C11 0.0197(5) 0.0268(6) 0.0247(6) 0.0058(5) 0.0080(4) 0.0027(5)
C12 0.0224(5) 0.0233(6) 0.0234(5) -0.0003(4) 0.0110(4) 0.0002(4)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.2570(18) 3_656 ?
N1 C1 1.4300(13) . ?
C1 C2 1.3937(15) . ?
C1 C6 1.3965(15) . ?
C2 C3 1.3897(15) . ?
C2 H2 0.987(14) . ?
C3 C4 1.3911(16) . ?
C3 H3 0.980(14) . ?
C4 C5 1.3929(16) . ?
C4 H4 0.984(13) . ?
C5 C6 1.3873(15) . ?
C5 H5 1.010(14) . ?
C6 H6 0.955(13) . ?
N2 N2 1.2450(19) 3_757 ?
N2 C7 1.4348(14) . ?
C7 C8 1.3973(16) . ?
C7 C12 1.3886(16) . ?
C8 C9 1.3906(15) . ?
C8 H8 0.973(14) . ?
C9 C10 1.3912(17) . ?
C9 H9 0.980(15) . ?
C10 C11 1.3859(17) . ?
C10 H10 0.972(14) . ?
C11 C12 1.3905(16) . ?
C11 H11 0.988(15) . ?
C12 H12 0.998(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 113.59(11) 3_656 . ?
C2 C1 N1 115.89(9) . . ?
C2 C1 C6 120.49(9) . . ?
C6 C1 N1 123.57(9) . . ?
C1 C2 H2 119.1(8) . . ?
C3 C2 C1 119.65(10) . . ?
C3 C2 H2 121.2(8) . . ?
C2 C3 C4 120.16(10) . . ?
C2 C3 H3 118.7(8) . . ?
C4 C3 H3 121.1(8) . . ?
C3 C4 C5 119.79(10) . . ?
C3 C4 H4 120.7(8) . . ?
C5 C4 H4 119.5(8) . . ?
C4 C5 H5 120.3(7) . . ?
C6 C5 C4 120.60(10) . . ?
C6 C5 H5 119.1(7) . . ?
C1 C6 H6 119.2(7) . . ?
C5 C6 C1 119.24(10) . . ?
C5 C6 H6 121.5(7) . . ?
N2 N2 C7 113.77(12) 3_757 . ?
C8 C7 N2 124.74(10) . . ?
C12 C7 N2 114.64(10) . . ?
C12 C7 C8 120.62(10) . . ?
C7 C8 H8 119.9(8) . . ?
C9 C8 C7 118.95(11) . . ?
C9 C8 H8 121.2(8) . . ?
C8 C9 C10 120.53(11) . . ?
C8 C9 H9 119.8(8) . . ?
C10 C9 H9 119.6(8) . . ?
C9 C10 H10 120.7(8) . . ?
C11 C10 C9 120.09(10) . . ?
C11 C10 H10 119.2(8) . . ?
C10 C11 C12 119.96(11) . . ?
C10 C11 H11 120.7(8) . . ?
C12 C11 H11 119.4(8) . . ?
C7 C12 C11 119.85(11) . . ?
C7 C12 H12 118.5(8) . . ?
C11 C12 H12 121.6(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -161.86(11) 3_656 . . . ?
N1 N1 C1 C6 20.55(16) 3_656 . . . ?
N1 C1 C2 C3 179.52(9) . . . . ?
N1 C1 C6 C5 178.42(9) . . . . ?
C1 C2 C3 C4 2.54(16) . . . . ?
C2 C1 C6 C5 0.94(15) . . . . ?
C2 C3 C4 C5 -0.42(16) . . . . ?
C3 C4 C5 C6 -1.46(16) . . . . ?
C4 C5 C6 C1 1.20(15) . . . . ?
C6 C1 C2 C3 -2.81(15) . . . . ?
N2 N2 C7 C8 9.69(18) 3_757 . . . ?
N2 N2 C7 C12 -170.37(12) 3_757 . . . ?
N2 C7 C8 C9 179.68(10) . . . . ?
N2 C7 C12 C11 179.53(10) . . . . ?
C7 C8 C9 C10 0.80(16) . . . . ?
C8 C7 C12 C11 -0.53(16) . . . . ?
C8 C9 C10 C11 -0.56(16) . . . . ?
C9 C10 C11 C12 -0.24(17) . . . . ?
C10 C11 C12 C7 0.78(17) . . . . ?
C12 C7 C8 C9 -0.26(16) . . . . ?

_shelx_res_file                  
;
TITL AF382_AlFr_ref_a.res in P2(1)/c
    af382_alfr_ref_a.res
    created by SHELXL-2018/3 at 17:09:48 on 06-Aug-2021
REM Old TITL AF382_AlFr_ref in P2(1)/c
REM SHELXT solution in P2(1)/c
REM R1 0.096, Rweak 0.105, Alpha 0.013, Orientation as input
REM Formula found by SHELXT: C12 N2
REM setting after Brouwstra
CELL 1.54184 14.984 5.6983 12.0341 90 112.452 90
ZERR 4 0.0004 0.0001 0.0003 0 0.003 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC N C H
UNIT 8 48 40

L.S. 10
PLAN  5
SIZE 0.041 0.13 0.208
TEMP -173(2)
BOND $H
LIST 4
CONF
fmap 2
acta
SHEL 999 0.8
REM <olex2.extras>
REM <HklSrc "%.\\AF382_AlFr_ref_a.hkl">
REM </olex2.extras>

WGHT    0.037500    0.379200
EXTI    0.004497
FVAR       0.90203
N1    1    0.490179    0.105644    0.505211    11.00000    0.01755    0.01774 =
         0.01646   -0.00012    0.00692    0.00114
C1    2    0.433028    0.138333    0.575784    11.00000    0.01481    0.01737 =
         0.01469   -0.00236    0.00481   -0.00124
C2    2    0.385713    0.353408    0.561990    11.00000    0.01955    0.01740 =
         0.01794    0.00011    0.00632   -0.00040
C3    2    0.328045    0.399068    0.626569    11.00000    0.01913    0.01838 =
         0.02237   -0.00290    0.00705    0.00196
C4    2    0.320642    0.234694    0.708090    11.00000    0.01708    0.02438 =
         0.02011   -0.00492    0.00848   -0.00166
C5    2    0.370728    0.023335    0.724258    11.00000    0.01863    0.02126 =
         0.01657   -0.00028    0.00641   -0.00309
C6    2    0.426290   -0.027231    0.657789    11.00000    0.01614    0.01642 =
         0.01680   -0.00085    0.00467    0.00004
H2    3    0.393711    0.470467    0.506095    11.00000    0.02204
H3    3    0.293974    0.549602    0.614495    11.00000    0.02206
H4    3    0.281426    0.267404    0.755869    11.00000    0.02161
H5    3    0.367712   -0.094533    0.785453    11.00000    0.02355
H6    3    0.460874   -0.171657    0.667720    11.00000    0.01583
N2    1    0.967657    0.073997    0.976692    11.00000    0.02162    0.02428 =
         0.02183    0.00116    0.00775    0.00194
C7    2    0.918779    0.047754    0.849061    11.00000    0.01639    0.02566 =
         0.01888    0.00147    0.00766   -0.00263
C8    2    0.929644   -0.143602    0.782700    11.00000    0.01657    0.02387 =
         0.02416    0.00278    0.00765    0.00079
C9    2    0.877505   -0.147859    0.659169    11.00000    0.01973    0.02659 =
         0.02424   -0.00444    0.01007   -0.00344
C10   2    0.816415    0.036856    0.602328    11.00000    0.01734    0.03306 =
         0.01745    0.00098    0.00571   -0.00313
C11   2    0.806414    0.226310    0.668868    11.00000    0.01967    0.02675 =
         0.02471    0.00581    0.00800    0.00271
C12   2    0.857226    0.231382    0.792656    11.00000    0.02238    0.02332 =
         0.02337   -0.00029    0.01096    0.00024
H8    3    0.973309   -0.270657    0.823137    11.00000    0.02575
H9    3    0.883844   -0.281856    0.611625    11.00000    0.02998
H10   3    0.779358    0.033749    0.516078    11.00000    0.02725
H11   3    0.763306    0.358387    0.629316    11.00000    0.03165
H12   3    0.850758    0.364668    0.842879    11.00000    0.02855
HKLF 4




REM  AF382_AlFr_ref_a.res in P2(1)/c
REM wR2 = 0.085557, GooF = S = 1.06034, Restrained GooF = 1.06034 for all data
REM R1 = 0.033510 for 1759 Fo > 4sig(Fo) and 0.036293 for all 1920 data
REM 168 parameters refined using 0 restraints

END

WGHT      0.0375      0.3792

REM Highest difference peak  0.244,  deepest hole -0.164,  1-sigma level  0.036
Q1    1   1.0185  0.0988  1.0473  11.00000  0.05    0.24
Q2    1   0.8754  0.1162  0.8225  11.00000  0.05    0.21
Q3    1   0.4214  0.2582  0.5821  11.00000  0.05    0.19
Q4    1   0.4189  0.0381  0.6018  11.00000  0.05    0.18
Q5    1   0.9295 -0.0301  0.8182  11.00000  0.05    0.17
;
_shelx_res_checksum              14444
_olex2_date_sample_data_collection 2021-08-03
_olex2_date_sample_submission    2021-07-29
_olex2_exptl_crystal_mounting_method 
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
 polyimide microloop and transferred to stream of cold 
 nitrogen (Oxford Cryostream 800).
;
_olex2_submission_original_sample_id AZOBEN
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.203
_oxdiff_exptl_absorpt_empirical_full_min 0.881
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_13p6GPa
_database_code_depnum_ccdc_archive 'CCDC 2336575'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_13p6GPa         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.323 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT411_AZO_13p6GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.79 Ang.  
RESPONSE: Intermolecular distances are strongly shortened at high 
pressure and atoms approach closer to one another than at ambient 
conditions or low temperature.
;
_vrf_PLAT149_AZO_13p6GPa         
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.13 Degree
RESPONSE: Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree.
;
_vrf_PLAT911_AZO_13p6GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        563 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3s (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-16
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   12.38(2)
_cell_length_b                   5.4468(7)
_cell_length_c                   10.725(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.53(13)
_cell_angle_gamma                90
_cell_volume                     657.7(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       13570000
_cell_measurement_reflns_used    392
_cell_measurement_theta_min      2.1860
_cell_measurement_theta_max      19.8680

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.28553
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         13570000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    0.50    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0363357274
_diffrn_orient_matrix_UB_12      0.0053354274
_diffrn_orient_matrix_UB_13      -0.0197209781
_diffrn_orient_matrix_UB_21      0.0028085037
_diffrn_orient_matrix_UB_22      0.0217467570
_diffrn_orient_matrix_UB_23      -0.0351224572
_diffrn_orient_matrix_UB_31      -0.0017686412
_diffrn_orient_matrix_UB_32      -0.0717676011
_diffrn_orient_matrix_UB_33      -0.0119919163
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2814
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.191
_diffrn_reflns_theta_max         21.372
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.194
_diffrn_measured_fraction_theta_full 0.323
_diffrn_reflns_Laue_measured_fraction_max 0.194
_diffrn_reflns_Laue_measured_fraction_full 0.323
_diffrn_reflns_point_group_measured_fraction_max 0.194
_diffrn_reflns_point_group_measured_fraction_full 0.323
_reflns_number_total             2814
_reflns_number_gt                2063
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
 Datasets from multiple crystals were merged in shelXL and their reflections 
 were scaled using HKLF 5 with BASF. The BASF parameter was refined to 26.5%. 
 A low-resolution reflection affected by beamstop [1 0 -4] was removed from 
 refinement. Some other reflections were removed as outliers. The anisotropic
 displacement parameters of all atoms were restrained to isotropic behqaviour
 using ISOR restraint.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1596P)²] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2814
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0819
_refine_ls_wR_factor_ref         0.2412
_refine_ls_wR_factor_gt          0.2257
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.075
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4905(6) 0.1114(5) 0.5076(5) 0.0232(19) Uani 1 1 d . U . . .
C1 C 0.4245(7) 0.1429(6) 0.5854(6) 0.023(2) Uani 1 1 d . U . . .
C2 C 0.3796(8) 0.3751(6) 0.5872(6) 0.022(2) Uani 1 1 d . U . . .
H2 H 0.386270 0.499182 0.531166 0.027 Uiso 1 1 calc R U . . .
C3 C 0.3249(8) 0.4182(7) 0.6739(6) 0.024(2) Uani 1 1 d . U . . .
H3 H 0.291722 0.571348 0.674256 0.029 Uiso 1 1 calc R U . . .
C4 C 0.3188(7) 0.2359(7) 0.7603(6) 0.023(2) Uani 1 1 d . U . . .
H4 H 0.282200 0.267763 0.818805 0.028 Uiso 1 1 calc R U . . .
C5 C 0.3664(8) 0.0079(6) 0.7606(6) 0.023(2) Uani 1 1 d . U . . .
H5 H 0.365084 -0.111936 0.821712 0.028 Uiso 1 1 calc R U . . .
C6 C 0.4159(8) -0.0420(6) 0.6702(6) 0.022(2) Uani 1 1 d . U . . .
H6 H 0.443657 -0.199010 0.665742 0.026 Uiso 1 1 calc R U . . .
N2 N 0.9859(7) 0.1078(5) 0.9792(5) 0.024(2) Uani 1 1 d . U . . .
C7 C 0.9219(8) 0.1216(7) 0.8362(6) 0.023(2) Uani 1 1 d . U . . .
C8 C 0.9141(8) -0.0719(6) 0.7480(6) 0.024(2) Uani 1 1 d . U . . .
H8 H 0.943449 -0.225982 0.783067 0.028 Uiso 1 1 calc R U . . .
C9 C 0.8626(8) -0.0338(6) 0.6084(6) 0.026(2) Uani 1 1 d . U . . .
H9 H 0.859386 -0.160041 0.548581 0.031 Uiso 1 1 calc R U . . .
C10 C 0.8162(8) 0.1930(7) 0.5587(6) 0.027(2) Uani 1 1 d . U . . .
H10 H 0.778732 0.218237 0.464552 0.032 Uiso 1 1 calc R U . . .
C11 C 0.8244(8) 0.3846(7) 0.6472(6) 0.025(2) Uani 1 1 d . U . . .
H11 H 0.794818 0.538452 0.611929 0.030 Uiso 1 1 calc R U . . .
C12 C 0.8758(8) 0.3493(6) 0.7861(6) 0.024(2) Uani 1 1 d . U . . .
H12 H 0.879565 0.476668 0.845477 0.029 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.025(6) 0.0267(16) 0.023(3) 0.0000(11) 0.014(4) 0.0012(15)
C1 0.024(7) 0.0275(17) 0.026(3) 0.0001(14) 0.017(4) 0.0008(19)
C2 0.018(7) 0.0287(17) 0.023(3) 0.0002(14) 0.012(4) -0.0004(18)
C3 0.022(7) 0.0272(17) 0.027(3) 0.0007(14) 0.015(4) 0.0035(18)
C4 0.018(7) 0.0307(18) 0.025(3) -0.0011(14) 0.013(5) -0.0003(19)
C5 0.019(7) 0.0278(18) 0.027(3) 0.0019(14) 0.015(4) 0.0007(18)
C6 0.017(6) 0.0267(16) 0.024(3) 0.0001(14) 0.013(4) 0.0005(19)
N2 0.024(6) 0.0289(17) 0.024(3) 0.0020(12) 0.014(4) 0.0006(16)
C7 0.020(7) 0.0301(18) 0.021(3) 0.0018(14) 0.011(4) -0.0005(19)
C8 0.023(7) 0.0249(16) 0.027(3) 0.0003(14) 0.014(4) -0.0016(18)
C9 0.028(7) 0.0294(18) 0.026(3) -0.0034(15) 0.016(4) -0.004(2)
C10 0.027(7) 0.0339(18) 0.026(3) 0.0011(16) 0.018(5) -0.001(2)
C11 0.022(7) 0.0291(18) 0.026(3) 0.0031(14) 0.013(5) 0.0021(19)
C12 0.021(7) 0.0283(18) 0.029(3) 0.0013(15) 0.017(4) 0.0013(19)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.259(6) 3_656 ?
N1 C1 1.399(6) . ?
C1 C2 1.385(6) . ?
C1 C6 1.391(5) . ?
C2 C3 1.380(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.253(7) 3_757 ?
N2 C7 1.405(9) . ?
C7 C12 1.378(7) . ?
C7 C8 1.393(5) . ?
C8 C9 1.378(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.373(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(9) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 112.5(4) 3_656 . ?
C2 C1 C6 120.8(4) . . ?
C2 C1 N1 117.2(3) . . ?
C6 C1 N1 121.6(4) . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 120.6(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 119.6(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 119.8(4) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N2 N2 C7 112.7(5) 3_757 . ?
C12 C7 C8 121.0(5) . . ?
C12 C7 N2 115.4(4) . . ?
C8 C7 N2 123.4(5) . . ?
C9 C8 C7 119.7(4) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C8 119.2(4) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 120.8(5) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 120.6(5) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 118.8(4) . . ?
C11 C12 H12 120.6 . . ?
C7 C12 H12 120.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -168.3(9) 3_656 . . . ?
N1 N1 C1 C6 19.1(12) 3_656 . . . ?
C6 C1 C2 C3 -0.8(12) . . . . ?
N1 C1 C2 C3 -173.4(7) . . . . ?
C1 C2 C3 C4 2.2(12) . . . . ?
C2 C3 C4 C5 -0.5(12) . . . . ?
C3 C4 C5 C6 -2.7(12) . . . . ?
C4 C5 C6 C1 4.2(13) . . . . ?
C2 C1 C6 C5 -2.4(13) . . . . ?
N1 C1 C6 C5 169.9(7) . . . . ?
N2 N2 C7 C12 172.4(7) 3_757 . . . ?
N2 N2 C7 C8 -13.7(11) 3_757 . . . ?
C12 C7 C8 C9 1.9(11) . . . . ?
N2 C7 C8 C9 -171.7(7) . . . . ?
C7 C8 C9 C10 -2.2(12) . . . . ?
C8 C9 C10 C11 2.3(11) . . . . ?
C9 C10 C11 C12 -2.1(11) . . . . ?
C10 C11 C12 C7 1.7(12) . . . . ?
C8 C7 C12 C11 -1.6(11) . . . . ?
N2 C7 C12 C11 172.5(7) . . . . ?


_shelx_res_file                  
;
TITL sample_0121_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 10:26:27 on 27-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  12.375157   5.446754  10.725006  90.0000 114.5262  90.0000
ZERR    4.00   0.019995   0.000673   0.006486   0.0000   0.1331   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
OMIT -2 0 6
OMIT -5 5 7
OMIT -7 -1 7
OMIT -9 0 10
OMIT 9 0 -10
OMIT 1 1 -6
OMIT -6 1 8
OMIT 1 0 -4
OMIT 4 0 -8
OMIT -4 0 8
OMIT 4 0 -8
OMIT -4 0 8
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.159600
BASF   0.26489
FVAR      23.42496
N1    1    0.490456    0.111361    0.507551    11.00000    0.02497    0.02666 =
         0.02262   -0.00001    0.01445    0.00118
C1    2    0.424477    0.142889    0.585367    11.00000    0.02407    0.02747 =
         0.02551    0.00012    0.01710    0.00080
C2    2    0.379633    0.375114    0.587151    11.00000    0.01823    0.02873 =
         0.02268    0.00020    0.01170   -0.00036
AFIX  43
H2    3    0.386270    0.499182    0.531166    11.00000   -1.20000
AFIX   0
C3    2    0.324852    0.418219    0.673940    11.00000    0.02215    0.02724 =
         0.02735    0.00071    0.01497    0.00349
AFIX  43
H3    3    0.291722    0.571348    0.674256    11.00000   -1.20000
AFIX   0
C4    2    0.318812    0.235921    0.760311    11.00000    0.01814    0.03068 =
         0.02493   -0.00108    0.01319   -0.00028
AFIX  43
H4    3    0.282200    0.267763    0.818805    11.00000   -1.20000
AFIX   0
C5    2    0.366421    0.007880    0.760590    11.00000    0.01898    0.02784 =
         0.02745    0.00186    0.01471    0.00069
AFIX  43
H5    3    0.365084   -0.111936    0.821712    11.00000   -1.20000
AFIX   0
C6    2    0.415914   -0.042044    0.670243    11.00000    0.01737    0.02673 =
         0.02433    0.00006    0.01254    0.00047
AFIX  43
H6    3    0.443657   -0.199010    0.665742    11.00000   -1.20000
AFIX   0
N2    1    0.985869    0.107793    0.979156    11.00000    0.02406    0.02890 =
         0.02428    0.00197    0.01424    0.00060
C7    2    0.921876    0.121563    0.836229    11.00000    0.01965    0.03005 =
         0.02140    0.00179    0.01111   -0.00048
C8    2    0.914073   -0.071867    0.747965    11.00000    0.02277    0.02488 =
         0.02714    0.00032    0.01433   -0.00160
AFIX  43
H8    3    0.943449   -0.225982    0.783067    11.00000   -1.20000
AFIX   0
C9    2    0.862621   -0.033765    0.608397    11.00000    0.02766    0.02935 =
         0.02649   -0.00337    0.01616   -0.00363
AFIX  43
H9    3    0.859386   -0.160041    0.548581    11.00000   -1.20000
AFIX   0
C10   2    0.816175    0.192971    0.558707    11.00000    0.02706    0.03394 =
         0.02608    0.00106    0.01778   -0.00142
AFIX  43
H10   3    0.778732    0.218237    0.464552    11.00000   -1.20000
AFIX   0
C11   2    0.824436    0.384561    0.647195    11.00000    0.02240    0.02912 =
         0.02626    0.00311    0.01301    0.00205
AFIX  43
H11   3    0.794818    0.538452    0.611929    11.00000   -1.20000
AFIX   0
C12   2    0.875816    0.349285    0.786074    11.00000    0.02132    0.02834 =
         0.02877    0.00130    0.01664    0.00133
AFIX  43
H12   3    0.879565    0.476668    0.845477    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0121_bn1 in P2(1)/c
REM wR2 = 0.2412, GooF = S = 1.096, Restrained GooF = 1.086 for all data
REM R1 = 0.0819 for 2063 Fo > 4sig(Fo) and 0.1049 for all 2814 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.1596      0.0000

REM Highest difference peak  0.397,  deepest hole -0.275,  1-sigma level  0.075
Q1    1   0.9550  0.1064  0.9058  11.00000  0.05    0.40
Q2    1   0.3903  0.2411  0.5800  11.00000  0.05    0.38
Q3    1   0.4634  0.1205  0.6450  11.00000  0.05    0.37
Q4    1   0.3270  0.3240  0.7312  11.00000  0.05    0.34
Q5    1   0.3724  0.3769  0.7557  11.00000  0.05    0.33
Q6    1   0.8690  0.3625  0.7286  11.00000  0.05    0.32
Q7    1   0.4142  0.0585  0.6205  11.00000  0.05    0.31
Q8    1   0.9109  0.0396  0.7832  11.00000  0.05    0.31
Q9    1   0.3363  0.1257  0.7562  11.00000  0.05    0.31
Q10   1   0.5401  0.0262  0.5118  11.00000  0.05    0.27
Q11   1   0.9061 -0.0192  0.6916  11.00000  0.05    0.27
Q12   1   0.8784  0.2375  0.8142  11.00000  0.05    0.26
Q13   1   0.8571  0.2831  0.6350  11.00000  0.05    0.25
Q14   1   1.0587  0.1596  1.0687  11.00000  0.05    0.24
Q15   1   0.7981  0.3160  0.5691  11.00000  0.05    0.24
Q16   1   0.8383  0.1401  0.7451  11.00000  0.05    0.23
Q17   1   0.9961 -0.0409  0.8529  11.00000  0.05    0.23
Q18   1   0.7991  0.0159  0.5287  11.00000  0.05    0.22
Q19   1   0.9589  0.2113  0.9995  11.00000  0.05    0.22
Q20   1   0.8784  0.1045  0.5850  11.00000  0.05    0.20
;
_shelx_res_checksum              25400
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_12p7GPa
_database_code_depnum_ccdc_archive 'CCDC 2336572'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_12p7GPa         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.327 Why?  
RESPONSE: Data were collected from a single crystal loaded within a diamond
anvil high-pressure cell. A large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT088_AZO_12p7GPa         
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.67 Note  
RESPONSE: A large part of reciprocal space was shadowed by the pressure 
cell.
;
_vrf_PLAT149_AZO_12p7GPa         
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.14 Degree
RESPONSE: Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree.
;
_vrf_PLAT340_AZO_12p7GPa         
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01208 Ang.  
RESPONSE: A large part of reciprocal space was shadowed by the pressure 
cell.
;
_vrf_PLAT411_AZO_12p7GPa         
;
PROBLEM: Short Inter H...H Contact  H2       ..H11      .       1.89 Ang.  
RESPONSE: Intermolecular distances are strongly shortened at high 
pressure and atoms approach closer to one another than at ambient 
conditions or low temperature.
;
_vrf_PLAT911_AZO_12p7GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        743 Report
RESPONSE: Data were collected from a single crystal loaded within a diamond
anvil high-pressure cell. A large part of reciprocal space
was shadowed by the pressure cell.
;

_audit_creation_method           'CIF-fill 1.3r (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-16
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   13.08(2)
_cell_length_b                   5.1502(8)
_cell_length_c                   10.814(7)
_cell_angle_alpha                90
_cell_angle_beta                 113.12(14)
_cell_angle_gamma                90
_cell_volume                     670.0(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       12680000
_cell_measurement_reflns_used    393
_cell_measurement_theta_min      2.1680
_cell_measurement_theta_max      20.0290

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.05830
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         12680000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    0.50    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0339339057
_diffrn_orient_matrix_UB_12      0.0083077128
_diffrn_orient_matrix_UB_13      -0.0185662607
_diffrn_orient_matrix_UB_21      0.0030785350
_diffrn_orient_matrix_UB_22      0.0223820344
_diffrn_orient_matrix_UB_23      -0.0347526789
_diffrn_orient_matrix_UB_31      -0.0027355995
_diffrn_orient_matrix_UB_32      -0.0757654498
_diffrn_orient_matrix_UB_33      -0.0121427818
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            1371
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.173
_diffrn_reflns_theta_max         21.790
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.187
_diffrn_measured_fraction_theta_full 0.327
_diffrn_reflns_Laue_measured_fraction_max 0.187
_diffrn_reflns_Laue_measured_fraction_full 0.327
_diffrn_reflns_point_group_measured_fraction_max 0.187
_diffrn_reflns_point_group_measured_fraction_full 0.327
_reflns_number_total             777
_reflns_number_gt                559
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal class for the 
 calculation of statistics and refinement. _reflns_Friedel_fraction is 
 defined as the number of unique Friedel pairs measured divided by the number 
 that would be possible theoretically, ignoring centric projections and 
 systematic absences.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          
;
The atomic displacement parameters 
of atoms N2A, N2B and C7 were restraint with RIGU keyword in ShelXL input 
('enhanced rigid bond' restraint for all bonds in the connectivity list).
The anisotropic displacement parameters 
of the disordered nitrogen atoms N2A and N2B were restrained to 
similar behaviour using SIMU restraint. The anisotropic displacement 
parameters of all atoms were restrained to isotropic behqaviour using ISOR 
restraint.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1433P)²+0.0471P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         777
_refine_ls_number_parameters     137
_refine_ls_number_restraints     102
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0902
_refine_ls_wR_factor_ref         0.2604
_refine_ls_wR_factor_gt          0.2457
_refine_ls_goodness_of_fit_ref   1.344
_refine_ls_restrained_S_all      1.344
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.062
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4882(8) 0.1168(6) 0.5059(5) 0.022(2) Uani 1 1 d . U . . .
C1 C 0.4288(9) 0.1477(7) 0.5864(6) 0.022(2) Uani 1 1 d . U . . .
C2 C 0.3779(10) 0.3846(7) 0.5796(6) 0.021(2) Uani 1 1 d . U . . .
H2 H 0.382793 0.513016 0.521752 0.026 Uiso 1 1 calc R U . . .
C3 C 0.3199(10) 0.4288(7) 0.6596(6) 0.026(2) Uani 1 1 d . U . . .
H3 H 0.281573 0.584143 0.651339 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3178(9) 0.2464(7) 0.7516(6) 0.022(2) Uani 1 1 d . U . . .
H4 H 0.280796 0.280917 0.807747 0.027 Uiso 1 1 calc R U . . .
C5 C 0.3707(10) 0.0134(7) 0.7597(6) 0.024(2) Uani 1 1 d . U . . .
H5 H 0.370179 -0.109462 0.822400 0.029 Uiso 1 1 calc R U . . .
C6 C 0.4249(10) -0.0411(7) 0.6756(6) 0.023(2) Uani 1 1 d . U . . .
H6 H 0.458233 -0.201967 0.678991 0.027 Uiso 1 1 calc R U . . .
N2A N 0.9646(16) 0.0792(11) 0.9754(12) 0.028(2) Uani 0.666(19) 1 d . U P A 1
N2B N 0.986(4) -0.094(2) 0.956(3) 0.030(3) Uani 0.334(19) 1 d . U P A 2
C7 C 0.9149(13) 0.0375(12) 0.8308(8) 0.047(2) Uani 1 1 d . U . . .
C8 C 0.9236(15) -0.1619(11) 0.7549(10) 0.046(2) Uani 1 1 d . U . . .
H8 H 0.963019 -0.310849 0.794658 0.056 Uiso 1 1 calc R U . . .
C9 C 0.8720(15) -0.1399(10) 0.6154(9) 0.047(2) Uani 1 1 d . U . . .
H9 H 0.875273 -0.275810 0.560500 0.056 Uiso 1 1 calc R U . . .
C10 C 0.8177(13) 0.0791(11) 0.5615(8) 0.042(2) Uani 1 1 d . U . . .
H10 H 0.786227 0.095767 0.468422 0.050 Uiso 1 1 calc R U . . .
C11 C 0.8067(12) 0.2806(9) 0.6391(8) 0.037(2) Uani 1 1 d . U . . .
H11 H 0.765641 0.427741 0.599597 0.045 Uiso 1 1 calc R U . . .
C12 C 0.8572(12) 0.2586(9) 0.7740(8) 0.035(2) Uani 1 1 d . U . . .
H12 H 0.852862 0.393990 0.828641 0.041 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.028(6) 0.0249(14) 0.018(2) 0.0005(11) 0.013(3) 0.003(2)
C1 0.028(6) 0.0235(15) 0.019(2) 0.0027(13) 0.014(3) 0.005(2)
C2 0.022(6) 0.0236(15) 0.023(2) 0.0003(15) 0.013(3) -0.002(2)
C3 0.033(6) 0.0236(15) 0.025(2) -0.0009(16) 0.014(3) 0.001(3)
C4 0.023(6) 0.0258(16) 0.020(2) 0.0013(14) 0.011(3) 0.004(2)
C5 0.027(6) 0.0292(17) 0.019(2) 0.0014(14) 0.012(3) 0.001(2)
C6 0.028(6) 0.0219(14) 0.021(2) 0.0001(14) 0.013(3) 0.003(2)
N2A 0.030(5) 0.032(2) 0.026(3) 0.001(2) 0.014(3) -0.001(3)
N2B 0.031(5) 0.035(3) 0.026(4) 0.000(3) 0.014(4) -0.003(4)
C7 0.050(6) 0.065(3) 0.029(3) 0.010(2) 0.020(3) -0.009(4)
C8 0.044(6) 0.038(2) 0.058(3) 0.009(2) 0.021(4) -0.002(3)
C9 0.047(6) 0.048(3) 0.051(3) -0.012(2) 0.025(4) 0.005(3)
C10 0.044(6) 0.061(3) 0.029(3) 0.001(2) 0.024(4) -0.011(3)
C11 0.035(6) 0.037(2) 0.042(3) 0.011(2) 0.016(4) 0.004(3)
C12 0.036(6) 0.043(2) 0.034(3) -0.0056(18) 0.024(4) -0.006(3)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.261(7) 3_656 ?
N1 C1 1.385(8) . ?
C1 C2 1.378(8) . ?
C1 C6 1.385(5) . ?
C2 C3 1.374(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2A N2A 1.19(3) 3_757 ?
N2A C7 1.454(15) . ?
N2B N2B 1.31(4) 3_757 ?
N2B C7 1.47(3) . ?
C7 C8 1.347(9) . ?
C7 C12 1.371(13) . ?
C8 C9 1.395(15) . ?
C8 H8 0.9300 . ?
C9 C10 1.339(14) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.350(12) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 113.2(5) 3_656 . ?
C2 C1 N1 116.5(3) . . ?
C2 C1 C6 120.7(5) . . ?
N1 C1 C6 122.7(6) . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 121.0(6) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.3(5) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 118.9(5) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N2A N2A C7 108.7(9) 3_757 . ?
N2B N2B C7 103(2) 3_757 . ?
C8 C7 C12 121.6(8) . . ?
C8 C7 N2A 131.2(10) . . ?
C12 C7 N2A 107.1(6) . . ?
C8 C7 N2B 91.9(9) . . ?
C12 C7 N2B 146.4(8) . . ?
C7 C8 C9 118.4(9) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C10 C9 C8 119.2(5) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 122.3(7) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
C12 C11 C10 118.1(8) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
C11 C12 C7 120.3(5) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -165.5(11) 3_656 . . . ?
N1 N1 C1 C6 18.3(16) 3_656 . . . ?
N1 C1 C2 C3 -178.5(9) . . . . ?
C6 C1 C2 C3 -2.2(15) . . . . ?
C1 C2 C3 C4 4.0(15) . . . . ?
C2 C3 C4 C5 -2.6(15) . . . . ?
C3 C4 C5 C6 -0.7(16) . . . . ?
C4 C5 C6 C1 2.5(16) . . . . ?
C2 C1 C6 C5 -1.1(15) . . . . ?
N1 C1 C6 C5 175.0(9) . . . . ?
N2A N2A C7 C8 12(3) 3_757 . . . ?
N2A N2A C7 C12 -163.8(15) 3_757 . . . ?
N2B N2B C7 C8 164(3) 3_757 . . . ?
N2B N2B C7 C12 -12(6) 3_757 . . . ?
C12 C7 C8 C9 0(2) . . . . ?
N2A C7 C8 C9 -175.3(13) . . . . ?
N2B C7 C8 C9 -177.5(17) . . . . ?
C7 C8 C9 C10 1(2) . . . . ?
C8 C9 C10 C11 -3(2) . . . . ?
C9 C10 C11 C12 3.1(19) . . . . ?
C10 C11 C12 C7 -1.8(18) . . . . ?
C8 C7 C12 C11 0.4(19) . . . . ?
N2A C7 C12 C11 176.6(12) . . . . ?
N2B C7 C12 C11 176(3) . . . . ?


_shelx_res_file                  
;
TITL sample_0113_bn1 in P2(1)/c
    sample_0113_bn1.res
    created by SHELXL-2018/3 at 22:59:18 on 24-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  13.080190   5.150183  10.814109  90.0000 113.1164  90.0000
ZERR    4.00   0.022285   0.000830   0.006826   0.0000   0.1368   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
SIMU 0.005 0.01 2 N2A N2B
rigU 0.005 0.01 N2A N2B C7
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.143300    0.047100
FVAR      22.76255   0.66566
N1    1    0.488177    0.116765    0.505925    11.00000    0.02779    0.02489 =
         0.01812    0.00051    0.01258    0.00334
C1    2    0.428750    0.147654    0.586363    11.00000    0.02791    0.02346 =
         0.01904    0.00266    0.01397    0.00527
C2    2    0.377919    0.384584    0.579647    11.00000    0.02214    0.02363 =
         0.02265    0.00033    0.01336   -0.00160
AFIX  43
H2    3    0.382793    0.513016    0.521752    11.00000   -1.20000
AFIX   0
C3    2    0.319929    0.428773    0.659556    11.00000    0.03270    0.02364 =
         0.02532   -0.00092    0.01440    0.00105
AFIX  43
H3    3    0.281573    0.584143    0.651339    11.00000   -1.20000
AFIX   0
C4    2    0.317782    0.246402    0.751604    11.00000    0.02339    0.02582 =
         0.01987    0.00129    0.01088    0.00421
AFIX  43
H4    3    0.280796    0.280917    0.807747    11.00000   -1.20000
AFIX   0
C5    2    0.370714    0.013442    0.759651    11.00000    0.02703    0.02921 =
         0.01928    0.00143    0.01233    0.00071
AFIX  43
H5    3    0.370179   -0.109462    0.822400    11.00000   -1.20000
AFIX   0
C6    2    0.424916   -0.041127    0.675608    11.00000    0.02821    0.02188 =
         0.02116    0.00012    0.01306    0.00263
AFIX  43
H6    3    0.458233   -0.201967    0.678991    11.00000   -1.20000
AFIX   0
rem SIMU 0.003 C7 > C12

PART 1 21.
N2A   1    0.964612    0.079192    0.975357    21.00000    0.03041    0.03200 =
         0.02560    0.00080    0.01422   -0.00120
PART 2 -21.
N2B   1    0.985959   -0.094308    0.955805   -21.00000    0.03106    0.03465 =
         0.02649    0.00010    0.01412   -0.00267
PART 0
C7    2    0.914886    0.037540    0.830834    11.00000    0.04960    0.06487 =
         0.02903    0.01004    0.01972   -0.00859
C8    2    0.923559   -0.161944    0.754946    11.00000    0.04422    0.03779 =
         0.05834    0.00917    0.02118   -0.00157
AFIX  43
H8    3    0.963019   -0.310849    0.794658    11.00000   -1.20000
AFIX   0
C9    2    0.871975   -0.139903    0.615441    11.00000    0.04654    0.04832 =
         0.05056   -0.01238    0.02530    0.00452
AFIX  43
H9    3    0.875273   -0.275810    0.560500    11.00000   -1.20000
AFIX   0
C10   2    0.817655    0.079133    0.561517    11.00000    0.04432    0.06084 =
         0.02940    0.00063    0.02423   -0.01076
AFIX  43
H10   3    0.786227    0.095767    0.468422    11.00000   -1.20000
AFIX   0
C11   2    0.806698    0.280600    0.639073    11.00000    0.03506    0.03679 =
         0.04163    0.01143    0.01641    0.00414
AFIX  43
H11   3    0.765641    0.427741    0.599597    11.00000   -1.20000
AFIX   0
C12   2    0.857206    0.258610    0.773998    11.00000    0.03559    0.04302 =
         0.03418   -0.00562    0.02363   -0.00587
AFIX  43
H12   3    0.852862    0.393990    0.828641    11.00000   -1.20000
AFIX   0
HKLF 4




REM  sample_0113_bn1 in P2(1)/c
REM wR2 = 0.2604, GooF = S = 1.344, Restrained GooF = 1.344 for all data
REM R1 = 0.0902 for 559 Fo > 4sig(Fo) and 0.1132 for all 777 data
REM 137 parameters refined using 102 restraints

END

WGHT      0.1931      0.1484

REM Highest difference peak  0.289,  deepest hole -0.220,  1-sigma level  0.062
Q1    1   0.3069  0.1782  0.5222  11.00000  0.05    0.29
Q2    1   0.3799  0.2468  0.5706  11.00000  0.05    0.28
Q3    1   0.5574 -0.0540  0.7514  11.00000  0.05    0.24
Q4    1   0.8739  0.1244  0.7975  11.00000  0.05    0.24
Q5    1   0.8229  0.1455  0.6273  11.00000  0.05    0.22
Q6    1   0.8731 -0.0562  0.7774  11.00000  0.05    0.22
Q7    1   0.5400  0.0258  0.5289  11.00000  0.05    0.22
Q8    1   0.4372  0.1824  0.8106  11.00000  0.05    0.21
Q9    1   0.3632  0.1257  0.7766  11.00000  0.05    0.20
Q10   1   0.4607 -0.1078  0.8508  11.00000  0.05    0.19
Q11   1   0.9424 -0.4275  0.6192  11.00000  0.05    0.19
Q12   1   0.3819  0.0496  0.4175  11.00000  0.05    0.18
Q13   1   0.8003 -0.0567  0.5484  11.00000  0.05    0.18
Q14   1   0.8679  0.1748  0.6234  11.00000  0.05    0.18
Q15   1   0.9813 -0.2303  0.6566  11.00000  0.05    0.18
Q16   1   0.6267  0.1121  0.5720  11.00000  0.05    0.18
Q17   1   0.7518 -0.1500  0.5678  11.00000  0.05    0.18
Q18   1   0.3884  0.0659  0.6118  11.00000  0.05    0.18
Q19   1   0.2277  0.4368  0.6104  11.00000  0.05    0.18
Q20   1   0.9888 -0.2145  0.7413  11.00000  0.05    0.17
;
_shelx_res_checksum              6688
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_0p5GPa
_database_code_depnum_ccdc_archive 'CCDC 2336565'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_0p5GPa          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.347 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT911_AZO_0p5GPa          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        711 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3q (K.Radacki, 2005-22)'
_audit_creation_date             2023-03-15
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   14.890(10)
_cell_length_b                   5.6496(3)
_cell_length_c                   11.905(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.44(5)
_cell_angle_gamma                90
_cell_volume                     925.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       541000
_cell_measurement_reflns_used    476
_cell_measurement_theta_min      1.9690
_cell_measurement_theta_max      20.9890

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.036
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.39330
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 Crystals were grown from saturated solution. For data collection the crystal 
 was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         541000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    0.50    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.0295648939
_diffrn_orient_matrix_UB_12      0.0061770604
_diffrn_orient_matrix_UB_13      0.0174259065
_diffrn_orient_matrix_UB_21      -0.0034531889
_diffrn_orient_matrix_UB_22      0.0193760361
_diffrn_orient_matrix_UB_23      0.0312854261
_diffrn_orient_matrix_UB_31      0.0016510905
_diffrn_orient_matrix_UB_32      -0.0696409015
_diffrn_orient_matrix_UB_33      0.0102498841
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            4254
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.974
_diffrn_reflns_theta_max         21.427
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.207
_diffrn_measured_fraction_theta_full 0.347
_diffrn_reflns_Laue_measured_fraction_max 0.207
_diffrn_reflns_Laue_measured_fraction_full 0.347
_diffrn_reflns_point_group_measured_fraction_max 0.207
_diffrn_reflns_point_group_measured_fraction_full 0.347
_reflns_number_total             4254
_reflns_number_gt                3205
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
The BASF parameter was refined to 45.1%. The anisotropic displacement 
parameters of the disordered nitrogen atoms N2A and N2B were restrained to 
similar behaviour using SIMU restraint. The anisotropic displacement 
parameters of all atoms were restrained to isotropic behqaviour using ISOR 
restraint.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1023P)²+0.0168P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4254
_refine_ls_number_parameters     138
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1700
_refine_ls_wR_factor_gt          0.1579
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.038
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4891(3) 0.1049(3) 0.5045(2) 0.0353(10) Uani 1 1 d . U . . .
C1 C 0.4323(3) 0.1377(3) 0.5761(2) 0.0304(11) Uani 1 1 d . U . . .
C2 C 0.3834(3) 0.3517(3) 0.5623(2) 0.0360(12) Uani 1 1 d . U . . .
H2 H 0.388984 0.464726 0.508534 0.043 Uiso 1 1 calc R U . . .
C3 C 0.3264(3) 0.3973(4) 0.6280(3) 0.0414(13) Uani 1 1 d . U . . .
H3 H 0.292188 0.538832 0.616764 0.050 Uiso 1 1 calc R U . . .
C4 C 0.3201(3) 0.2311(4) 0.7111(3) 0.0413(14) Uani 1 1 d . U . . .
H4 H 0.282159 0.261625 0.755918 0.050 Uiso 1 1 calc R U . . .
C5 C 0.3707(3) 0.0207(4) 0.7265(3) 0.0386(13) Uani 1 1 d . U . . .
H5 H 0.367299 -0.088666 0.783097 0.046 Uiso 1 1 calc R U . . .
C6 C 0.4262(3) -0.0303(3) 0.6594(2) 0.0323(11) Uani 1 1 d . U . . .
H6 H 0.458994 -0.173738 0.669360 0.039 Uiso 1 1 calc R U . . .
N2A N 0.9689(5) 0.0764(4) 0.9766(6) 0.0434(18) Uani 0.897(15) 1 d . U P A 1
N2B N 0.994(5) -0.086(4) 0.960(5) 0.045(4) Uani 0.103(15) 1 d . U P A 2
C7 C 0.9194(4) 0.0522(4) 0.8481(3) 0.0423(15) Uani 1 1 d . U . . .
C8 C 0.9280(4) -0.1386(4) 0.7777(3) 0.0474(15) Uani 1 1 d . U . . .
H8 H 0.968348 -0.265810 0.813924 0.057 Uiso 1 1 calc R U . . .
C9 C 0.8758(5) -0.1350(5) 0.6543(4) 0.0527(18) Uani 1 1 d . U . . .
H9 H 0.881149 -0.261181 0.607095 0.063 Uiso 1 1 calc R U . . .
C10 C 0.8156(4) 0.0530(5) 0.5992(3) 0.0489(19) Uani 1 1 d . U . . .
H10 H 0.780608 0.053585 0.515683 0.059 Uiso 1 1 calc R U . . .
C11 C 0.8082(4) 0.2412(5) 0.6705(3) 0.0521(17) Uani 1 1 d . U . . .
H11 H 0.768367 0.369214 0.634413 0.063 Uiso 1 1 calc R U . . .
C12 C 0.8591(4) 0.2388(4) 0.7931(3) 0.0510(17) Uani 1 1 d . U . . .
H12 H 0.852934 0.364504 0.840053 0.061 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.042(3) 0.0335(8) 0.0358(14) 0.0005(6) 0.021(2) 0.0032(9)
C1 0.032(4) 0.0310(9) 0.0288(15) -0.0023(7) 0.013(2) -0.0003(9)
C2 0.039(4) 0.0337(10) 0.0363(17) 0.0019(7) 0.015(2) 0.0043(10)
C3 0.043(4) 0.0365(11) 0.049(2) -0.0037(8) 0.022(3) 0.0063(11)
C4 0.041(5) 0.0475(12) 0.0423(19) -0.0074(9) 0.023(3) -0.0014(12)
C5 0.041(4) 0.0438(11) 0.0349(18) 0.0009(8) 0.019(3) -0.0038(12)
C6 0.032(4) 0.0331(9) 0.0319(16) 0.0010(7) 0.013(2) 0.0011(10)
N2A 0.047(5) 0.0455(12) 0.038(3) 0.0022(10) 0.016(4) 0.0074(13)
N2B 0.048(8) 0.050(5) 0.037(6) 0.003(5) 0.015(7) 0.005(5)
C7 0.038(5) 0.0531(13) 0.037(2) 0.0051(9) 0.016(3) -0.0022(14)
C8 0.043(5) 0.0487(13) 0.052(2) 0.0046(10) 0.019(3) 0.0030(13)
C9 0.053(6) 0.0558(15) 0.055(2) -0.0108(12) 0.027(4) -0.0042(16)
C10 0.039(6) 0.0702(18) 0.034(2) 0.0025(11) 0.010(4) -0.0053(17)
C11 0.050(6) 0.0563(15) 0.052(2) 0.0132(11) 0.021(3) 0.0111(16)
C12 0.060(6) 0.0509(13) 0.048(2) 0.0007(10) 0.026(3) 0.0041(15)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.244(3) 3_656 ?
N1 C1 1.424(3) . ?
C1 C2 1.389(4) . ?
C1 C6 1.400(2) . ?
C2 C3 1.380(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2A N2A 1.233(11) 3_757 ?
N2A C7 1.429(8) . ?
N2B N2B 1.32(8) 3_757 ?
N2B C7 1.58(5) . ?
C7 C12 1.378(6) . ?
C7 C8 1.401(4) . ?
C8 C9 1.375(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.383(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.391(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.363(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 114.2(2) 3_656 . ?
C2 C1 C6 120.1(2) . . ?
C2 C1 N1 116.57(16) . . ?
C6 C1 N1 123.3(2) . . ?
C3 C2 C1 120.23(18) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.26(19) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 118.9(2) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N2A N2A C7 114.0(5) 3_757 . ?
N2B N2B C7 96(4) 3_757 . ?
C12 C7 C8 119.8(4) . . ?
C12 C7 N2A 114.3(2) . . ?
C8 C7 N2A 125.9(4) . . ?
C12 C7 N2B 154.2(12) . . ?
C8 C7 N2B 86.0(12) . . ?
C9 C8 C7 118.9(3) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 121.2(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C11 119.0(4) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C7 120.8(2) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -162.5(4) 3_656 . . . ?
N1 N1 C1 C6 19.1(6) 3_656 . . . ?
C6 C1 C2 C3 -1.8(6) . . . . ?
N1 C1 C2 C3 179.7(3) . . . . ?
C1 C2 C3 C4 1.9(6) . . . . ?
C2 C3 C4 C5 -0.4(6) . . . . ?
C3 C4 C5 C6 -1.1(6) . . . . ?
C4 C5 C6 C1 1.2(6) . . . . ?
C2 C1 C6 C5 0.2(5) . . . . ?
N1 C1 C6 C5 178.6(3) . . . . ?
N2A N2A C7 C12 -172.0(5) 3_757 . . . ?
N2A N2A C7 C8 7.8(8) 3_757 . . . ?
N2B N2B C7 C12 -8(7) 3_757 . . . ?
N2B N2B C7 C8 172(4) 3_757 . . . ?
C12 C7 C8 C9 0.2(6) . . . . ?
N2A C7 C8 C9 -179.5(4) . . . . ?
N2B C7 C8 C9 -180.0(16) . . . . ?
C7 C8 C9 C10 0.1(6) . . . . ?
C8 C9 C10 C11 0.1(6) . . . . ?
C9 C10 C11 C12 -0.5(6) . . . . ?
C10 C11 C12 C7 0.8(7) . . . . ?
C8 C7 C12 C11 -0.7(6) . . . . ?
N2A C7 C12 C11 179.1(4) . . . . ?
N2B C7 C12 C11 180(4) . . . . ?


_shelx_res_file                  
;
TITL sample_0017_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 19:36:09 on 23-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  14.890300   5.649635  11.904565  90.0000 112.4381  90.0000
ZERR    4.00   0.009910   0.000278   0.002933   0.0000   0.0533   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
OMIT 4 1 -2
OMIT -2 -1 0
OMIT 1 1 -1
OMIT -1 1 1
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.03
FMAP 2
PLAN 20
WGHT    0.102300    0.016800
BASF   0.45080
FVAR      21.78596   0.89674
N1    1    0.489117    0.104853    0.504522    11.00000    0.04180    0.03350 =
         0.03584    0.00045    0.02062    0.00315
C1    2    0.432306    0.137701    0.576122    11.00000    0.03228    0.03096 =
         0.02877   -0.00234    0.01262   -0.00026
C2    2    0.383352    0.351718    0.562275    11.00000    0.03861    0.03368 =
         0.03630    0.00189    0.01510    0.00431
AFIX  43
H2    3    0.388984    0.464726    0.508534    11.00000   -1.20000
AFIX   0
C3    2    0.326384    0.397264    0.627979    11.00000    0.04289    0.03654 =
         0.04902   -0.00371    0.02214    0.00628
AFIX  43
H3    3    0.292188    0.538832    0.616764    11.00000   -1.20000
AFIX   0
C4    2    0.320135    0.231136    0.711071    11.00000    0.04072    0.04753 =
         0.04234   -0.00742    0.02329   -0.00137
AFIX  43
H4    3    0.282159    0.261625    0.755918    11.00000   -1.20000
AFIX   0
C5    2    0.370698    0.020735    0.726479    11.00000    0.04100    0.04384 =
         0.03487    0.00094    0.01883   -0.00375
AFIX  43
H5    3    0.367299   -0.088666    0.783097    11.00000   -1.20000
AFIX   0
C6    2    0.426222   -0.030277    0.659384    11.00000    0.03245    0.03305 =
         0.03193    0.00096    0.01277    0.00105
AFIX  43
H6    3    0.458994   -0.173738    0.669360    11.00000   -1.20000
AFIX   0
REM SIMU 0.003 C7 > C12
SIMU 0.003 N2A N2B
PART 1 21.
N2A   1    0.968883    0.076444    0.976621    21.00000    0.04671    0.04553 =
         0.03798    0.00224    0.01607    0.00740
PART 2 -21.
N2B   1    0.993583   -0.085803    0.960100   -21.00000    0.04773    0.04967 =
         0.03686    0.00264    0.01519    0.00473
PART 0
C7    2    0.919430    0.052177    0.848088    11.00000    0.03822    0.05314 =
         0.03687    0.00512    0.01581   -0.00216
C8    2    0.928011   -0.138645    0.777748    11.00000    0.04325    0.04867 =
         0.05154    0.00464    0.01933    0.00302
AFIX  43
H8    3    0.968348   -0.265810    0.813924    11.00000   -1.20000
AFIX   0
C9    2    0.875849   -0.134983    0.654349    11.00000    0.05297    0.05583 =
         0.05473   -0.01076    0.02656   -0.00422
AFIX  43
H9    3    0.881149   -0.261181    0.607095    11.00000   -1.20000
AFIX   0
C10   2    0.815623    0.053034    0.599214    11.00000    0.03864    0.07024 =
         0.03442    0.00250    0.01011   -0.00528
AFIX  43
H10   3    0.780608    0.053585    0.515683    11.00000   -1.20000
AFIX   0
C11   2    0.808196    0.241191    0.670495    11.00000    0.04960    0.05626 =
         0.05219    0.01324    0.02124    0.01107
AFIX  43
H11   3    0.768367    0.369214    0.634413    11.00000   -1.20000
AFIX   0
C12   2    0.859056    0.238773    0.793052    11.00000    0.05968    0.05092 =
         0.04759    0.00072    0.02631    0.00409
AFIX  43
H12   3    0.852934    0.364504    0.840053    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0017_bn1 in P2(1)/c
REM wR2 = 0.1700, GooF = S = 1.058, Restrained GooF = 1.047 for all data
REM R1 = 0.0579 for 3205 Fo > 4sig(Fo) and 0.0746 for all 4254 data
REM 138 parameters refined using 96 restraints

END

WGHT      0.1027      0.0119

REM Highest difference peak  0.224,  deepest hole -0.181,  1-sigma level  0.038
Q1    1   0.3976  0.2325  0.5644  11.00000  0.05    0.22
Q2    1   0.4403  0.2642  0.5987  11.00000  0.05    0.21
Q3    1   0.9292 -0.0519  0.8316  11.00000  0.05    0.19
Q4    1   0.4239  0.0543  0.6054  11.00000  0.05    0.19
Q5    1   0.3979  0.0115  0.6903  11.00000  0.05    0.18
Q6    1   0.3189  0.3057  0.6621  11.00000  0.05    0.18
Q7    1   0.3538  0.3472  0.5962  11.00000  0.05    0.17
Q8    1   0.8218  0.1420  0.6385  11.00000  0.05    0.14
Q9    1   0.7728  0.1114  0.6193  11.00000  0.05    0.13
Q10   1   0.4487  0.0917  0.5420  11.00000  0.05    0.12
Q11   1   0.5401  0.3133  0.5036  11.00000  0.05    0.12
Q12   1   0.5899  0.2526  0.5812  11.00000  0.05    0.12
Q13   1   0.8501  0.1159  0.8125  11.00000  0.05    0.12
Q14   1   0.3348  0.1210  0.6969  11.00000  0.05    0.11
Q15   1   0.7073  0.1522  0.5033  11.00000  0.05    0.11
Q16   1   0.4908  0.2116  0.4706  11.00000  0.05    0.11
Q17   1   0.9110  0.4164  0.6605  11.00000  0.05    0.10
Q18   1   0.6772  0.2191  0.6006  11.00000  0.05    0.10
Q19   1   1.0000  0.0000  1.0000  10.50000  0.05    0.10
Q20   1   0.3610 -0.3336  0.8906  11.00000  0.05    0.10
;
_shelx_res_checksum              86563
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_16p3GPa
_database_code_depnum_ccdc_archive 'CCDC 2336580'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_16p3GPa         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.347 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT411_AZO_16p3GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.72 Ang.  
RESPONSE: Intermolecular distances are strongly shortened at high 
pressure and atoms approach closer to one another than at ambient 
conditions or low temperature.
;
_vrf_PLAT149_AZO_16p3GPa         
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.11 Degree
RESPONSE: Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree.
;
_vrf_PLAT911_AZO_16p3GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        600 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3s (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-16
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   12.096(15)
_cell_length_b                   5.5053(4)
_cell_length_c                   10.570(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.42(11)
_cell_angle_gamma                90
_cell_volume                     635.8(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       16270000
_cell_measurement_reflns_used    560
_cell_measurement_theta_min      2.2150
_cell_measurement_theta_max      20.5710

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.904
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.052
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51425
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         16270000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    1.00    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0373977066
_diffrn_orient_matrix_UB_12      0.0066280721
_diffrn_orient_matrix_UB_13      -0.0207737585
_diffrn_orient_matrix_UB_21      0.0031785939
_diffrn_orient_matrix_UB_22      0.0221993728
_diffrn_orient_matrix_UB_23      -0.0352918604
_diffrn_orient_matrix_UB_31      -0.0023672286
_diffrn_orient_matrix_UB_32      -0.0706905607
_diffrn_orient_matrix_UB_33      -0.0128928516
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2557
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.223
_diffrn_reflns_theta_max         21.432
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.204
_diffrn_measured_fraction_theta_full 0.347
_diffrn_reflns_Laue_measured_fraction_max 0.204
_diffrn_reflns_Laue_measured_fraction_full 0.347
_diffrn_reflns_point_group_measured_fraction_max 0.204
_diffrn_reflns_point_group_measured_fraction_full 0.347
_reflns_number_total             2557
_reflns_number_gt                2049
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
 Datasets from multiple crystals were merged in shelXL and their reflections 
 were scaled using HKLF 5 with BASF. The BASF parameter was refined to 22.6%. 
 The Uii displacement parameters of all atoms were restrained with ISOR 
 keyword to approximate isotropic behavior.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1508P)²] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2557
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.2122
_refine_ls_wR_factor_gt          0.2026
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.069
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4907(6) 0.1104(4) 0.5082(4) 0.0224(18) Uani 1 1 d . U . . .
C1 C 0.4230(6) 0.1418(4) 0.5858(4) 0.0226(18) Uani 1 1 d . U . . .
C2 C 0.3807(6) 0.3728(4) 0.5904(4) 0.0198(19) Uani 1 1 d . U . . .
H2 H 0.389051 0.496898 0.535397 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3257(7) 0.4145(5) 0.6790(5) 0.0228(19) Uani 1 1 d . U . . .
H3 H 0.293654 0.567020 0.681588 0.027 Uiso 1 1 calc R U . . .
C4 C 0.3182(7) 0.2319(5) 0.7634(5) 0.0234(19) Uani 1 1 d . U . . .
H4 H 0.282210 0.263237 0.823782 0.028 Uiso 1 1 calc R U . . .
C5 C 0.3627(7) 0.0038(4) 0.7602(4) 0.0225(19) Uani 1 1 d . U . . .
H5 H 0.359267 -0.117017 0.819954 0.027 Uiso 1 1 calc R U . . .
C6 C 0.4122(6) -0.0439(5) 0.6684(4) 0.0211(18) Uani 1 1 d . U . . .
H6 H 0.438480 -0.199974 0.661353 0.025 Uiso 1 1 calc R U . . .
N2 N 0.9898(6) 0.1086(4) 0.9804(4) 0.0232(18) Uani 1 1 d . U . . .
C7 C 0.9222(7) 0.1307(5) 0.8356(4) 0.0212(18) Uani 1 1 d . U . . .
C8 C 0.9094(6) -0.0604(5) 0.7439(4) 0.0227(18) Uani 1 1 d . U . . .
H8 H 0.935860 -0.215718 0.778026 0.027 Uiso 1 1 calc R U . . .
C9 C 0.8572(7) -0.0159(5) 0.6023(5) 0.023(2) Uani 1 1 d . U . . .
H9 H 0.848692 -0.140378 0.539358 0.028 Uiso 1 1 calc R U . . .
C10 C 0.8178(7) 0.2142(4) 0.5551(4) 0.024(2) Uani 1 1 d . U . . .
H10 H 0.782080 0.244664 0.459276 0.029 Uiso 1 1 calc R U . . .
C11 C 0.8299(7) 0.4005(4) 0.6463(5) 0.023(2) Uani 1 1 d . U . . .
H11 H 0.803029 0.555428 0.611714 0.028 Uiso 1 1 calc R U . . .
C12 C 0.8813(7) 0.3602(5) 0.7879(4) 0.0237(19) Uani 1 1 d . U . . .
H12 H 0.888257 0.485244 0.850092 0.028 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.028(6) 0.0252(11) 0.015(2) -0.0003(8) 0.010(3) 0.0012(13)
C1 0.029(6) 0.0250(11) 0.017(2) 0.0000(10) 0.013(3) 0.0008(16)
C2 0.019(6) 0.0254(12) 0.012(2) -0.0001(9) 0.005(4) -0.0005(15)
C3 0.027(6) 0.0249(11) 0.016(2) -0.0007(10) 0.009(4) 0.0007(15)
C4 0.028(6) 0.0266(12) 0.018(2) 0.0001(10) 0.012(4) 0.0012(16)
C5 0.024(6) 0.0257(12) 0.016(2) 0.0016(10) 0.007(4) 0.0010(16)
C6 0.022(6) 0.0236(11) 0.017(2) -0.0007(10) 0.008(3) -0.0007(15)
N2 0.027(6) 0.0264(12) 0.017(2) 0.0018(9) 0.010(3) 0.0010(13)
C7 0.022(6) 0.0267(12) 0.014(2) 0.0011(10) 0.007(4) 0.0005(16)
C8 0.025(6) 0.0241(11) 0.020(2) 0.0019(10) 0.011(4) 0.0012(15)
C9 0.023(6) 0.0270(12) 0.018(2) -0.0002(10) 0.008(4) -0.0013(16)
C10 0.026(6) 0.0275(12) 0.018(2) 0.0017(11) 0.008(4) -0.0005(17)
C11 0.027(6) 0.0263(12) 0.017(2) 0.0030(10) 0.009(4) 0.0025(15)
C12 0.029(6) 0.0251(12) 0.016(2) 0.0010(10) 0.009(4) 0.0006(16)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.261(4) 3_656 ?
N1 C1 1.396(5) . ?
C1 C2 1.379(5) . ?
C1 C6 1.387(4) . ?
C2 C3 1.382(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.255(5) 3_757 ?
N2 C7 1.397(7) . ?
C7 C12 1.371(5) . ?
C7 C8 1.393(4) . ?
C8 C9 1.373(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.370(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 112.6(3) 3_656 . ?
C2 C1 C6 121.4(3) . . ?
C2 C1 N1 117.0(2) . . ?
C6 C1 N1 121.0(3) . . ?
C1 C2 C3 118.1(2) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2 N2 C7 112.6(4) 3_757 . ?
C12 C7 C8 121.7(4) . . ?
C12 C7 N2 115.6(3) . . ?
C8 C7 N2 122.3(4) . . ?
C9 C8 C7 119.0(3) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C10 C9 C8 119.2(3) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 121.3(4) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 118.2(3) . . ?
C11 C12 H12 120.9 . . ?
C7 C12 H12 120.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -169.8(7) 3_656 . . . ?
N1 N1 C1 C6 18.1(10) 3_656 . . . ?
C6 C1 C2 C3 -0.7(10) . . . . ?
N1 C1 C2 C3 -172.8(6) . . . . ?
C1 C2 C3 C4 2.4(10) . . . . ?
C2 C3 C4 C5 -1.1(10) . . . . ?
C3 C4 C5 C6 -2.0(10) . . . . ?
C4 C5 C6 C1 3.7(10) . . . . ?
C2 C1 C6 C5 -2.4(10) . . . . ?
N1 C1 C6 C5 169.4(6) . . . . ?
N2 N2 C7 C12 170.8(6) 3_757 . . . ?
N2 N2 C7 C8 -16.6(10) 3_757 . . . ?
C12 C7 C8 C9 1.6(10) . . . . ?
N2 C7 C8 C9 -170.6(6) . . . . ?
C7 C8 C9 C10 -0.8(9) . . . . ?
C8 C9 C10 C11 0.3(9) . . . . ?
C9 C10 C11 C12 -0.5(10) . . . . ?
C10 C11 C12 C7 1.3(10) . . . . ?
C8 C7 C12 C11 -1.8(10) . . . . ?
N2 C7 C12 C11 170.8(6) . . . . ?


_shelx_res_file                  
;
TITL sample_0139_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 10:39:53 on 27-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  12.096189   5.505272  10.570285  90.0000 115.4169  90.0000
ZERR    4.00   0.014934   0.000414   0.005483   0.0000   0.1083   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.150800
BASF   0.22630
FVAR      25.36414
N1    1    0.490668    0.110362    0.508217    11.00000    0.02758    0.02523 =
         0.01497   -0.00027    0.00958    0.00123
C1    2    0.422968    0.141807    0.585783    11.00000    0.02897    0.02497 =
         0.01715    0.00000    0.01293    0.00083
C2    2    0.380739    0.372787    0.590381    11.00000    0.01914    0.02540 =
         0.01249   -0.00009    0.00459   -0.00054
AFIX  43
H2    3    0.389051    0.496898    0.535397    11.00000   -1.20000
AFIX   0
C3    2    0.325713    0.414519    0.679049    11.00000    0.02707    0.02491 =
         0.01623   -0.00067    0.00909    0.00068
AFIX  43
H3    3    0.293654    0.567020    0.681588    11.00000   -1.20000
AFIX   0
C4    2    0.318170    0.231855    0.763391    11.00000    0.02760    0.02662 =
         0.01819    0.00011    0.01205    0.00125
AFIX  43
H4    3    0.282210    0.263237    0.823782    11.00000   -1.20000
AFIX   0
C5    2    0.362711    0.003782    0.760245    11.00000    0.02398    0.02573 =
         0.01597    0.00157    0.00692    0.00103
AFIX  43
H5    3    0.359267   -0.117017    0.819954    11.00000   -1.20000
AFIX   0
C6    2    0.412201   -0.043925    0.668389    11.00000    0.02234    0.02356 =
         0.01706   -0.00071    0.00827   -0.00068
AFIX  43
H6    3    0.438480   -0.199974    0.661353    11.00000   -1.20000
AFIX   0
N2    1    0.989766    0.108588    0.980381    11.00000    0.02746    0.02638 =
         0.01666    0.00177    0.01028    0.00095
C7    2    0.922186    0.130724    0.835573    11.00000    0.02208    0.02673 =
         0.01406    0.00112    0.00702    0.00054
C8    2    0.909416   -0.060367    0.743889    11.00000    0.02528    0.02412 =
         0.01968    0.00193    0.01051    0.00121
AFIX  43
H8    3    0.935860   -0.215718    0.778026    11.00000   -1.20000
AFIX   0
C9    2    0.857190   -0.015868    0.602341    11.00000    0.02334    0.02696 =
         0.01824   -0.00019    0.00817   -0.00126
AFIX  43
H9    3    0.848692   -0.140378    0.539358    11.00000   -1.20000
AFIX   0
C10   2    0.817772    0.214189    0.555088    11.00000    0.02571    0.02746 =
         0.01769    0.00169    0.00850   -0.00046
AFIX  43
H10   3    0.782080    0.244664    0.459276    11.00000   -1.20000
AFIX   0
C11   2    0.829905    0.400483    0.646289    11.00000    0.02660    0.02626 =
         0.01657    0.00302    0.00895    0.00250
AFIX  43
H11   3    0.803029    0.555428    0.611714    11.00000   -1.20000
AFIX   0
C12   2    0.881296    0.360242    0.787932    11.00000    0.02949    0.02509 =
         0.01608    0.00099    0.00926    0.00062
AFIX  43
H12   3    0.888257    0.485244    0.850092    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0139_bn1 in P2(1)/c
REM wR2 = 0.2122, GooF = S = 1.123, Restrained GooF = 1.112 for all data
REM R1 = 0.0687 for 2049 Fo > 4sig(Fo) and 0.0778 for all 2557 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.1508      0.0000

REM Highest difference peak  0.341,  deepest hole -0.253,  1-sigma level  0.069
Q1    1   0.9708  0.0353  0.8104  11.00000  0.05    0.34
Q2    1   0.8777  0.3075  0.6216  11.00000  0.05    0.33
Q3    1   0.8850  0.2210  0.7931  11.00000  0.05    0.32
Q4    1   0.8634  0.1144  0.5922  11.00000  0.05    0.31
Q5    1   0.8771  0.0472  0.7841  11.00000  0.05    0.30
Q6    1   0.8152  0.0852  0.5570  11.00000  0.05    0.30
Q7    1   0.3675  0.0607  0.6091  11.00000  0.05    0.30
Q8    1   0.9384  0.2642  0.8402  11.00000  0.05    0.29
Q9    1   0.7933  0.2964  0.5931  11.00000  0.05    0.28
Q10   1   0.2750  0.3196  0.6996  11.00000  0.05    0.26
Q11   1   1.0502  0.2018  1.0380  11.00000  0.05    0.26
Q12   1   0.3737  0.3135  0.7419  11.00000  0.05    0.25
Q13   1   0.3416  0.1159  0.7580  11.00000  0.05    0.25
Q14   1   0.4173  0.2411  0.6085  11.00000  0.05    0.24
Q15   1   0.5000  0.0000  0.5000  10.50000  0.05    0.22
Q16   1   0.9687 -0.0114  0.9736  11.00000  0.05    0.22
Q17   1   0.9095  0.2819  0.7316  11.00000  0.05    0.21
Q18   1   0.4320  0.0555  0.6221  11.00000  0.05    0.21
Q19   1   1.0094 -0.1001  0.8106  11.00000  0.05    0.21
Q20   1   0.8718 -0.0046  0.6745  11.00000  0.05    0.21
;
_shelx_res_checksum              82801
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_16p8GPa
_database_code_depnum_ccdc_archive 'CCDC 2336581'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_16p8GPa         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.350 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT411_AZO_16p8GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.71 Ang.  
RESPONSE: Intermolecular distances are strongly shortened at high 
pressure and atoms approach closer to one another than at ambient 
conditions or low temperature.
;
_vrf_PLAT149_AZO_16p8GPa         
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.10 Degree
RESPONSE: Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree.
;
_vrf_PLAT911_AZO_16p8GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        586 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3s (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-16
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   12.064(14)
_cell_length_b                   5.5054(4)
_cell_length_c                   10.545(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.46(10)
_cell_angle_gamma                90
_cell_volume                     632.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       16750000
_cell_measurement_reflns_used    601
_cell_measurement_theta_min      2.2240
_cell_measurement_theta_max      20.1210

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.914
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.052
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.42699
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         16750000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    1.00    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0375911837
_diffrn_orient_matrix_UB_12      0.0066144151
_diffrn_orient_matrix_UB_13      -0.0209062966
_diffrn_orient_matrix_UB_21      0.0031781837
_diffrn_orient_matrix_UB_22      0.0222506791
_diffrn_orient_matrix_UB_23      -0.0353223087
_diffrn_orient_matrix_UB_31      -0.0023566234
_diffrn_orient_matrix_UB_32      -0.0706025382
_diffrn_orient_matrix_UB_33      -0.0129468655
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2591
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0134
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.228
_diffrn_reflns_theta_max         21.460
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.206
_diffrn_measured_fraction_theta_full 0.350
_diffrn_reflns_Laue_measured_fraction_max 0.206
_diffrn_reflns_Laue_measured_fraction_full 0.350
_diffrn_reflns_point_group_measured_fraction_max 0.206
_diffrn_reflns_point_group_measured_fraction_full 0.350
_reflns_number_total             2591
_reflns_number_gt                2118
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
 Datasets from multiple crystals were merged in shelXL and their reflections 
 were scaled using HKLF 5 with BASF. The BASF parameter was refined to 18.5%. 
 2 low-resolution reflections, that were affected by beamstop, were removed 
 from refinemet ( [2 -1 0] [3 -1 -1] ).
 The Uii displacement parameters of all atoms were restrained with ISOR 
 keyword to approximate isotropic behavior.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1377P)²+0.0064P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2591
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.1988
_refine_ls_wR_factor_gt          0.1906
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.067
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4904(5) 0.1102(3) 0.5081(4) 0.0174(17) Uani 1 1 d . U . . .
C1 C 0.4229(6) 0.1416(4) 0.5858(4) 0.0188(17) Uani 1 1 d . U . . .
C2 C 0.3805(6) 0.3727(4) 0.5905(4) 0.0170(19) Uani 1 1 d . U . . .
H2 H 0.388589 0.496857 0.535283 0.020 Uiso 1 1 calc R U . . .
C3 C 0.3257(6) 0.4142(4) 0.6796(4) 0.0188(18) Uani 1 1 d . U . . .
H3 H 0.293701 0.566771 0.682413 0.023 Uiso 1 1 calc R U . . .
C4 C 0.3183(6) 0.2315(4) 0.7638(4) 0.0187(18) Uani 1 1 d . U . . .
H4 H 0.282776 0.263022 0.824896 0.022 Uiso 1 1 calc R U . . .
C5 C 0.3620(6) 0.0033(4) 0.7600(4) 0.0189(19) Uani 1 1 d . U . . .
H5 H 0.357828 -0.117864 0.819251 0.023 Uiso 1 1 calc R U . . .
C6 C 0.4119(6) -0.0443(4) 0.6680(4) 0.0177(18) Uani 1 1 d . U . . .
H6 H 0.438119 -0.200312 0.660757 0.021 Uiso 1 1 calc R U . . .
N2 N 0.9899(5) 0.1086(3) 0.9804(4) 0.0205(17) Uani 1 1 d . U . . .
C7 C 0.9220(6) 0.1318(4) 0.8354(4) 0.0187(18) Uani 1 1 d . U . . .
C8 C 0.9086(6) -0.0589(4) 0.7433(4) 0.0196(18) Uani 1 1 d . U . . .
H8 H 0.934533 -0.214582 0.777394 0.024 Uiso 1 1 calc R U . . .
C9 C 0.8566(6) -0.0144(4) 0.6016(4) 0.0209(19) Uani 1 1 d . U . . .
H9 H 0.847960 -0.138884 0.538427 0.025 Uiso 1 1 calc R U . . .
C10 C 0.8176(6) 0.2161(4) 0.5544(4) 0.0213(19) Uani 1 1 d . U . . .
H10 H 0.781560 0.246763 0.458373 0.026 Uiso 1 1 calc R U . . .
C11 C 0.8305(7) 0.4026(4) 0.6461(4) 0.0202(19) Uani 1 1 d . U . . .
H11 H 0.804376 0.557982 0.611554 0.024 Uiso 1 1 calc R U . . .
C12 C 0.8817(6) 0.3620(4) 0.7880(4) 0.0206(18) Uani 1 1 d . U . . .
H12 H 0.888955 0.486902 0.850508 0.025 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.014(5) 0.0233(10) 0.013(2) -0.0002(8) 0.004(3) 0.0019(12)
C1 0.020(5) 0.0224(10) 0.015(2) -0.0001(9) 0.008(3) 0.0008(14)
C2 0.013(6) 0.0234(11) 0.012(2) 0.0002(9) 0.002(4) 0.0001(14)
C3 0.017(6) 0.0227(10) 0.015(2) -0.0002(9) 0.004(3) 0.0014(14)
C4 0.015(6) 0.0250(11) 0.015(2) 0.0000(10) 0.006(3) 0.0009(15)
C5 0.015(6) 0.0232(11) 0.015(2) 0.0008(9) 0.003(4) 0.0007(14)
C6 0.014(6) 0.0214(10) 0.016(2) -0.0002(9) 0.004(3) 0.0002(14)
N2 0.022(5) 0.0235(11) 0.015(2) 0.0015(8) 0.007(3) 0.0010(12)
C7 0.017(6) 0.0236(11) 0.014(2) 0.0013(9) 0.005(3) 0.0006(14)
C8 0.018(6) 0.0213(10) 0.019(2) 0.0020(10) 0.008(3) 0.0022(14)
C9 0.019(6) 0.0247(11) 0.018(2) -0.0009(10) 0.006(4) -0.0019(15)
C10 0.021(6) 0.0242(11) 0.017(2) 0.0013(10) 0.007(4) -0.0001(15)
C11 0.020(6) 0.0239(11) 0.016(2) 0.0030(9) 0.006(4) 0.0028(15)
C12 0.022(6) 0.0221(11) 0.016(2) 0.0015(9) 0.007(4) 0.0013(14)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.261(4) 3_656 ?
N1 C1 1.393(5) . ?
C1 C2 1.380(4) . ?
C1 C6 1.383(3) . ?
C2 C3 1.380(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.254(4) 3_757 ?
N2 C7 1.396(6) . ?
C7 C12 1.372(4) . ?
C7 C8 1.392(4) . ?
C8 C9 1.371(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 112.8(3) 3_656 . ?
C2 C1 C6 121.5(3) . . ?
C2 C1 N1 117.0(2) . . ?
C6 C1 N1 121.0(3) . . ?
C3 C2 C1 118.0(2) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 121.4(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
N2 N2 C7 112.8(4) 3_757 . ?
C12 C7 C8 121.7(4) . . ?
C12 C7 N2 115.6(3) . . ?
C8 C7 N2 122.2(3) . . ?
C9 C8 C7 119.1(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 119.1(3) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 121.3(4) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 118.1(3) . . ?
C11 C12 H12 120.9 . . ?
C7 C12 H12 120.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -170.0(7) 3_656 . . . ?
N1 N1 C1 C6 17.5(10) 3_656 . . . ?
C6 C1 C2 C3 -0.3(9) . . . . ?
N1 C1 C2 C3 -172.7(5) . . . . ?
C1 C2 C3 C4 2.3(9) . . . . ?
C2 C3 C4 C5 -1.5(10) . . . . ?
C3 C4 C5 C6 -1.4(10) . . . . ?
C4 C5 C6 C1 3.3(9) . . . . ?
C2 C1 C6 C5 -2.5(10) . . . . ?
N1 C1 C6 C5 169.6(5) . . . . ?
N2 N2 C7 C12 171.0(6) 3_757 . . . ?
N2 N2 C7 C8 -16.5(9) 3_757 . . . ?
C12 C7 C8 C9 1.7(9) . . . . ?
N2 C7 C8 C9 -170.4(5) . . . . ?
C7 C8 C9 C10 -1.0(9) . . . . ?
C8 C9 C10 C11 0.6(9) . . . . ?
C9 C10 C11 C12 -0.9(9) . . . . ?
C10 C11 C12 C7 1.6(10) . . . . ?
C8 C7 C12 C11 -2.0(9) . . . . ?
N2 C7 C12 C11 170.6(5) . . . . ?


_shelx_res_file                  
;
TITL sample_0142_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 10:41:59 on 27-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  12.064271   5.505401  10.544994  90.0000 115.4649  90.0000
ZERR    4.00   0.013642   0.000384   0.004945   0.0000   0.0987   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
OMIT 2 -1 0
OMIT 3 -1 -1
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.137700    0.006400
BASF   0.18496
FVAR      24.09453
N1    1    0.490391    0.110235    0.508097    11.00000    0.01369    0.02334 =
         0.01304   -0.00024    0.00380    0.00185
C1    2    0.422860    0.141574    0.585847    11.00000    0.01984    0.02243 =
         0.01457   -0.00009    0.00793    0.00077
C2    2    0.380470    0.372734    0.590520    11.00000    0.01258    0.02342 =
         0.01203    0.00015    0.00235    0.00014
AFIX  43
H2    3    0.388589    0.496857    0.535283    11.00000   -1.20000
AFIX   0
C3    2    0.325688    0.414245    0.679568    11.00000    0.01673    0.02271 =
         0.01461   -0.00024    0.00445    0.00136
AFIX  43
H3    3    0.293701    0.566771    0.682413    11.00000   -1.20000
AFIX   0
C4    2    0.318254    0.231458    0.763840    11.00000    0.01488    0.02503 =
         0.01532    0.00003    0.00577    0.00094
AFIX  43
H4    3    0.282776    0.263022    0.824896    11.00000   -1.20000
AFIX   0
C5    2    0.361972    0.003345    0.760010    11.00000    0.01544    0.02323 =
         0.01465    0.00084    0.00330    0.00073
AFIX  43
H5    3    0.357828   -0.117864    0.819251    11.00000   -1.20000
AFIX   0
C6    2    0.411852   -0.044281    0.667985    11.00000    0.01358    0.02143 =
         0.01581   -0.00022    0.00427    0.00016
AFIX  43
H6    3    0.438119   -0.200312    0.660757    11.00000   -1.20000
AFIX   0
N2    1    0.989879    0.108578    0.980400    11.00000    0.02161    0.02355 =
         0.01537    0.00146    0.00704    0.00100
C7    2    0.922015    0.131839    0.835406    11.00000    0.01731    0.02362 =
         0.01381    0.00127    0.00536    0.00059
C8    2    0.908582   -0.058930    0.743280    11.00000    0.01837    0.02134 =
         0.01890    0.00195    0.00774    0.00215
AFIX  43
H8    3    0.934533   -0.214582    0.777394    11.00000   -1.20000
AFIX   0
C9    2    0.856611   -0.014408    0.601630    11.00000    0.01872    0.02471 =
         0.01786   -0.00090    0.00646   -0.00195
AFIX  43
H9    3    0.847960   -0.138884    0.538427    11.00000   -1.20000
AFIX   0
C10   2    0.817568    0.216139    0.554438    11.00000    0.02084    0.02420 =
         0.01718    0.00132    0.00659   -0.00012
AFIX  43
H10   3    0.781560    0.246763    0.458373    11.00000   -1.20000
AFIX   0
C11   2    0.830549    0.402636    0.646092    11.00000    0.01954    0.02390 =
         0.01563    0.00298    0.00612    0.00282
AFIX  43
H11   3    0.804376    0.557982    0.611554    11.00000   -1.20000
AFIX   0
C12   2    0.881726    0.362019    0.788035    11.00000    0.02208    0.02209 =
         0.01632    0.00153    0.00710    0.00130
AFIX  43
H12   3    0.888955    0.486902    0.850508    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0142_bn1 in P2(1)/c
REM wR2 = 0.1988, GooF = S = 1.140, Restrained GooF = 1.128 for all data
REM R1 = 0.0642 for 2118 Fo > 4sig(Fo) and 0.0723 for all 2591 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.1377      0.0064

REM Highest difference peak  0.326,  deepest hole -0.260,  1-sigma level  0.067
Q1    1   0.9868  0.0344  0.8241  11.00000  0.05    0.33
Q2    1   0.8632  0.3258  0.6081  11.00000  0.05    0.31
Q3    1   0.8617  0.3830  0.7288  11.00000  0.05    0.31
Q4    1   0.3477  0.3903  0.6348  11.00000  0.05    0.31
Q5    1   0.3770 -0.0376  0.7162  11.00000  0.05    0.30
Q6    1   0.3107  0.3135  0.7171  11.00000  0.05    0.29
Q7    1   0.8733 -0.0370  0.6591  11.00000  0.05    0.28
Q8    1   0.3723  0.3311  0.7426  11.00000  0.05    0.27
Q9    1   1.0665  0.1957  1.0553  11.00000  0.05    0.27
Q10   1   0.8876  0.2325  0.7983  11.00000  0.05    0.26
Q11   1   0.8809  0.0387  0.7843  11.00000  0.05    0.26
Q12   1   0.9502  0.2761  0.8499  11.00000  0.05    0.25
Q13   1   0.4527  0.2542  0.6324  11.00000  0.05    0.25
Q14   1   0.7934  0.3013  0.5916  11.00000  0.05    0.25
Q15   1   0.8166  0.0817  0.5554  11.00000  0.05    0.24
Q16   1   0.9110  0.3069  0.7279  11.00000  0.05    0.23
Q17   1   0.2123  0.1438  0.6335  11.00000  0.05    0.21
Q18   1   0.8831  0.1326  0.5949  11.00000  0.05    0.20
Q19   1   0.2617  0.3420  0.6091  11.00000  0.05    0.20
Q20   1   0.4753  0.1778  0.4608  11.00000  0.05    0.20
;
_shelx_res_checksum              53690
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_17p2GPa
_database_code_depnum_ccdc_archive 'CCDC 2336582'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_17p2GPa         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.352 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT411_AZO_17p2GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.70 Ang.  
RESPONSE: Intermolecular distances are strongly shortened at high 
pressure and atoms approach closer to one another than at ambient 
conditions or low temperature.
;
_vrf_PLAT149_AZO_17p2GPa         
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.10 Degree
RESPONSE: Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree.
;
_vrf_PLAT911_AZO_17p2GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        562 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3s (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-16
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   12.013(14)
_cell_length_b                   5.5124(4)
_cell_length_c                   10.539(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.68(10)
_cell_angle_gamma                90
_cell_volume                     629.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       17250000
_cell_measurement_reflns_used    580
_cell_measurement_theta_min      2.2270
_cell_measurement_theta_max      20.8130

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.924
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.052
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.31570
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         17250000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    1.00    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0377543169
_diffrn_orient_matrix_UB_12      0.0065905078
_diffrn_orient_matrix_UB_13      -0.0210201156
_diffrn_orient_matrix_UB_21      0.0031743943
_diffrn_orient_matrix_UB_22      0.0222934305
_diffrn_orient_matrix_UB_23      -0.0353641107
_diffrn_orient_matrix_UB_31      -0.0023621070
_diffrn_orient_matrix_UB_32      -0.0705634538
_diffrn_orient_matrix_UB_33      -0.0130001885
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2693
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0131
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.230
_diffrn_reflns_theta_max         21.457
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.207
_diffrn_measured_fraction_theta_full 0.352
_diffrn_reflns_Laue_measured_fraction_max 0.207
_diffrn_reflns_Laue_measured_fraction_full 0.352
_diffrn_reflns_point_group_measured_fraction_max 0.207
_diffrn_reflns_point_group_measured_fraction_full 0.352
_reflns_number_total             2693
_reflns_number_gt                2205
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
 Datasets from multiple crystals were merged in shelXL and their reflections 
 were scaled using HKLF 5 with BASF. The BASF parameter was refined to 21.3%. 
 The Uii displacement parameters of all atoms were restrained with ISOR 
 keyword to approximate isotropic behavior.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1296P)²+0.0124P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2693
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1817
_refine_ls_wR_factor_gt          0.1745
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.070
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4905(5) 0.1104(3) 0.5081(3) 0.0170(16) Uani 1 1 d . U . . .
C1 C 0.4225(6) 0.1416(4) 0.5857(4) 0.0194(16) Uani 1 1 d . U . . .
C2 C 0.3803(6) 0.3728(4) 0.5907(4) 0.0165(17) Uani 1 1 d . U . . .
H2 H 0.388489 0.496818 0.535503 0.020 Uiso 1 1 calc R U . . .
C3 C 0.3256(6) 0.4142(4) 0.6800(4) 0.0191(17) Uani 1 1 d . U . . .
H3 H 0.293866 0.566837 0.683103 0.023 Uiso 1 1 calc R U . . .
C4 C 0.3178(6) 0.2314(4) 0.7641(4) 0.0197(17) Uani 1 1 d . U . . .
H4 H 0.281894 0.262758 0.824917 0.024 Uiso 1 1 calc R U . . .
C5 C 0.3619(6) 0.0031(4) 0.7603(4) 0.0189(17) Uani 1 1 d . U . . .
H5 H 0.358280 -0.117988 0.819888 0.023 Uiso 1 1 calc R U . . .
C6 C 0.4112(5) -0.0441(4) 0.6678(4) 0.0181(17) Uani 1 1 d . U . . .
H6 H 0.437086 -0.200159 0.660006 0.022 Uiso 1 1 calc R U . . .
N2 N 0.9902(5) 0.1089(3) 0.9806(3) 0.0186(16) Uani 1 1 d . U . . .
C7 C 0.9223(6) 0.1327(4) 0.8355(4) 0.0169(17) Uani 1 1 d . U . . .
C8 C 0.9084(6) -0.0579(4) 0.7431(4) 0.0185(17) Uani 1 1 d . U . . .
H8 H 0.934360 -0.213531 0.777260 0.022 Uiso 1 1 calc R U . . .
C9 C 0.8560(6) -0.0129(4) 0.6010(4) 0.0201(18) Uani 1 1 d . U . . .
H9 H 0.846546 -0.137280 0.537517 0.024 Uiso 1 1 calc R U . . .
C10 C 0.8177(6) 0.2178(4) 0.5540(4) 0.0200(18) Uani 1 1 d . U . . .
H10 H 0.781844 0.248950 0.457742 0.024 Uiso 1 1 calc R U . . .
C11 C 0.8311(6) 0.4038(4) 0.6461(4) 0.0191(17) Uani 1 1 d . U . . .
H11 H 0.805079 0.559174 0.611535 0.023 Uiso 1 1 calc R U . . .
C12 C 0.8826(6) 0.3631(4) 0.7884(4) 0.0201(18) Uani 1 1 d . U . . .
H12 H 0.890328 0.487826 0.851091 0.024 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.015(5) 0.0226(10) 0.0116(19) -0.0003(7) 0.004(3) 0.0019(11)
C1 0.024(5) 0.0217(9) 0.014(2) 0.0000(8) 0.010(3) 0.0012(13)
C2 0.013(5) 0.0221(10) 0.012(2) -0.0002(8) 0.003(3) -0.0001(13)
C3 0.020(5) 0.0214(10) 0.014(2) -0.0002(9) 0.006(3) 0.0013(13)
C4 0.020(5) 0.0238(10) 0.015(2) 0.0004(9) 0.008(3) 0.0013(14)
C5 0.018(6) 0.0224(10) 0.014(2) 0.0007(9) 0.005(3) 0.0002(14)
C6 0.017(5) 0.0205(9) 0.015(2) 0.0000(8) 0.005(3) 0.0005(13)
N2 0.018(5) 0.0228(10) 0.014(2) 0.0010(8) 0.006(3) 0.0002(12)
C7 0.014(5) 0.0230(10) 0.011(2) 0.0015(8) 0.004(3) 0.0005(13)
C8 0.017(5) 0.0210(9) 0.016(2) 0.0016(9) 0.006(3) 0.0005(13)
C9 0.019(6) 0.0232(10) 0.016(2) -0.0002(9) 0.007(4) -0.0010(14)
C10 0.019(6) 0.0235(10) 0.015(2) 0.0012(9) 0.005(3) -0.0011(14)
C11 0.019(5) 0.0225(10) 0.014(2) 0.0022(9) 0.005(3) 0.0014(13)
C12 0.022(6) 0.0215(10) 0.015(2) 0.0016(9) 0.006(3) 0.0021(14)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.263(4) 3_656 ?
N1 C1 1.395(4) . ?
C1 C2 1.381(4) . ?
C1 C6 1.384(3) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.258(4) 3_757 ?
N2 C7 1.393(6) . ?
C7 C12 1.372(4) . ?
C7 C8 1.393(3) . ?
C8 C9 1.373(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.370(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 112.6(3) 3_656 . ?
C2 C1 C6 121.5(2) . . ?
C2 C1 N1 117.0(2) . . ?
C6 C1 N1 121.0(3) . . ?
C3 C2 C1 118.0(2) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 121.2(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 119.2(2) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2 N2 C7 112.7(3) 3_757 . ?
C12 C7 C8 121.9(3) . . ?
C12 C7 N2 115.5(3) . . ?
C8 C7 N2 122.1(3) . . ?
C9 C8 C7 119.0(3) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C10 C9 C8 119.1(2) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 121.3(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 118.0(2) . . ?
C11 C12 H12 121.0 . . ?
C7 C12 H12 121.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -170.2(6) 3_656 . . . ?
N1 N1 C1 C6 17.6(8) 3_656 . . . ?
C6 C1 C2 C3 -0.3(9) . . . . ?
N1 C1 C2 C3 -172.5(5) . . . . ?
C1 C2 C3 C4 2.1(8) . . . . ?
C2 C3 C4 C5 -1.1(9) . . . . ?
C3 C4 C5 C6 -1.9(9) . . . . ?
C4 C5 C6 C1 3.8(9) . . . . ?
C2 C1 C6 C5 -2.7(9) . . . . ?
N1 C1 C6 C5 169.2(5) . . . . ?
N2 N2 C7 C12 171.0(5) 3_757 . . . ?
N2 N2 C7 C8 -16.5(8) 3_757 . . . ?
C12 C7 C8 C9 1.4(8) . . . . ?
N2 C7 C8 C9 -170.6(5) . . . . ?
C7 C8 C9 C10 -0.6(8) . . . . ?
C8 C9 C10 C11 0.2(8) . . . . ?
C9 C10 C11 C12 -0.6(9) . . . . ?
C10 C11 C12 C7 1.4(9) . . . . ?
C8 C7 C12 C11 -1.8(8) . . . . ?
N2 C7 C12 C11 170.7(5) . . . . ?


_shelx_res_file                  
;
TITL sample_0145_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 10:44:35 on 27-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  12.012921   5.512375  10.539011  90.0000 115.6789  90.0000
ZERR    4.00   0.013706   0.000352   0.005060   0.0000   0.1005   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.129600    0.012400
BASF   0.21283
FVAR      25.39241
N1    1    0.490461    0.110364    0.508118    11.00000    0.01461    0.02262 =
         0.01161   -0.00030    0.00378    0.00188
C1    2    0.422458    0.141596    0.585735    11.00000    0.02385    0.02167 =
         0.01445   -0.00005    0.00995    0.00122
C2    2    0.380290    0.372773    0.590668    11.00000    0.01310    0.02208 =
         0.01173   -0.00023    0.00294   -0.00013
AFIX  43
H2    3    0.388489    0.496818    0.535503    11.00000   -1.20000
AFIX   0
C3    2    0.325585    0.414225    0.679966    11.00000    0.02046    0.02135 =
         0.01363   -0.00020    0.00552    0.00131
AFIX  43
H3    3    0.293866    0.566837    0.683103    11.00000   -1.20000
AFIX   0
C4    2    0.317759    0.231399    0.764143    11.00000    0.02015    0.02379 =
         0.01541    0.00043    0.00793    0.00133
AFIX  43
H4    3    0.281894    0.262758    0.824917    11.00000   -1.20000
AFIX   0
C5    2    0.361889    0.003059    0.760314    11.00000    0.01758    0.02244 =
         0.01432    0.00067    0.00475    0.00022
AFIX  43
H5    3    0.358280   -0.117988    0.819888    11.00000   -1.20000
AFIX   0
C6    2    0.411233   -0.044126    0.667754    11.00000    0.01737    0.02054 =
         0.01478    0.00003    0.00535    0.00047
AFIX  43
H6    3    0.437086   -0.200159    0.660006    11.00000   -1.20000
AFIX   0
N2    1    0.990219    0.108946    0.980575    11.00000    0.01802    0.02281 =
         0.01412    0.00096    0.00605    0.00018
C7    2    0.922277    0.132721    0.835486    11.00000    0.01426    0.02300 =
         0.01143    0.00149    0.00357    0.00054
C8    2    0.908434   -0.057937    0.743136    11.00000    0.01701    0.02101 =
         0.01645    0.00157    0.00627    0.00047
AFIX  43
H8    3    0.934360   -0.213531    0.777260    11.00000   -1.20000
AFIX   0
C9    2    0.855965   -0.012903    0.601002    11.00000    0.01942    0.02321 =
         0.01649   -0.00018    0.00654   -0.00096
AFIX  43
H9    3    0.846546   -0.137280    0.537517    11.00000   -1.20000
AFIX   0
C10   2    0.817670    0.217791    0.553967    11.00000    0.01880    0.02355 =
         0.01521    0.00116    0.00519   -0.00107
AFIX  43
H10   3    0.781844    0.248950    0.457742    11.00000   -1.20000
AFIX   0
C11   2    0.831134    0.403834    0.646061    11.00000    0.01857    0.02246 =
         0.01439    0.00216    0.00539    0.00136
AFIX  43
H11   3    0.805079    0.559174    0.611535    11.00000   -1.20000
AFIX   0
C12   2    0.882579    0.363088    0.788384    11.00000    0.02212    0.02151 =
         0.01488    0.00158    0.00639    0.00208
AFIX  43
H12   3    0.890328    0.487826    0.851091    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0145_bn1 in P2(1)/c
REM wR2 = 0.1817, GooF = S = 1.105, Restrained GooF = 1.093 for all data
REM R1 = 0.0603 for 2205 Fo > 4sig(Fo) and 0.0679 for all 2693 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.1297      0.0124

REM Highest difference peak  0.350,  deepest hole -0.258,  1-sigma level  0.070
Q1    1   0.3557  0.3166  0.7329  11.00000  0.05    0.35
Q2    1   0.8756  0.3054  0.6224  11.00000  0.05    0.33
Q3    1   0.8176  0.0830  0.5544  11.00000  0.05    0.31
Q4    1   0.4592  0.1949  0.4570  11.00000  0.05    0.29
Q5    1   0.8607  0.3886  0.7300  11.00000  0.05    0.29
Q6    1   0.8656  0.2289  0.7866  11.00000  0.05    0.28
Q7    1   0.9508  0.0417  0.7991  11.00000  0.05    0.28
Q8    1   0.8823  0.0484  0.7845  11.00000  0.05    0.28
Q9    1   0.3518  0.3939  0.6334  11.00000  0.05    0.28
Q10   1   0.7943  0.3054  0.5939  11.00000  0.05    0.28
Q11   1   0.8826 -0.0199  0.6750  11.00000  0.05    0.27
Q12   1   0.4201  0.0640  0.6247  11.00000  0.05    0.26
Q13   1   0.8651  0.1240  0.5978  11.00000  0.05    0.25
Q14   1   0.9515  0.2701  0.8478  11.00000  0.05    0.24
Q15   1   1.0495  0.2013  1.0389  11.00000  0.05    0.24
Q16   1   0.4297  0.2554  0.6261  11.00000  0.05    0.22
Q17   1   0.3819  0.0014  0.7155  11.00000  0.05    0.22
Q18   1   0.3720  0.1203  0.7830  11.00000  0.05    0.21
Q19   1   0.4388  0.0128  0.4482  11.00000  0.05    0.20
Q20   1   0.4607  0.0547  0.5531  11.00000  0.05    0.20
;
_shelx_res_checksum              6460
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_14p7GPa
_database_code_depnum_ccdc_archive 'CCDC 2336577'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_14p7GPa         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.326 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT411_AZO_14p7GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.75 Ang.  
RESPONSE: Intermolecular distances are strongly shortened at high 
pressure and atoms approach closer to one another than at ambient 
conditions or low temperature.
;
_vrf_PLAT149_AZO_14p7GPa         
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.14 Degree
RESPONSE: Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree.
;
_vrf_PLAT911_AZO_14p7GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        640 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3s (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-16
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   12.24(2)
_cell_length_b                   5.4747(6)
_cell_length_c                   10.639(7)
_cell_angle_alpha                90
_cell_angle_beta                 114.84(14)
_cell_angle_gamma                90
_cell_volume                     647.1(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       14668000
_cell_measurement_reflns_used    540
_cell_measurement_theta_min      2.2050
_cell_measurement_theta_max      20.6350

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.870
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.35873
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         14668000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    1.00    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0367283272
_diffrn_orient_matrix_UB_12      0.0067074348
_diffrn_orient_matrix_UB_13      -0.0201739387
_diffrn_orient_matrix_UB_21      0.0031364109
_diffrn_orient_matrix_UB_22      0.0220886357
_diffrn_orient_matrix_UB_23      -0.0351681348
_diffrn_orient_matrix_UB_31      -0.0024340660
_diffrn_orient_matrix_UB_32      -0.0711824347
_diffrn_orient_matrix_UB_33      -0.0127019434
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2408
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.209
_diffrn_reflns_theta_max         21.408
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.194
_diffrn_measured_fraction_theta_full 0.326
_diffrn_reflns_Laue_measured_fraction_max 0.194
_diffrn_reflns_Laue_measured_fraction_full 0.326
_diffrn_reflns_point_group_measured_fraction_max 0.194
_diffrn_reflns_point_group_measured_fraction_full 0.326
_reflns_number_total             2408
_reflns_number_gt                1818
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
 Datasets from multiple crystals were merged in shelXL and their reflections 
 were scaled using HKLF 5 with BASF. The BASF parameter was refined to 42.8%. 
 Some reflections were removed from refinement as outliers. 
 The Uii displacement parameters of all atoms were restrained with ISOR 
 keyword to approximate isotropic behavior.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2408
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0907
_refine_ls_wR_factor_ref         0.2777
_refine_ls_wR_factor_gt          0.2564
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.072
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4908(7) 0.1110(5) 0.5080(5) 0.026(2) Uani 1 1 d . U . . .
C1 C 0.4235(8) 0.1416(6) 0.5854(6) 0.026(2) Uani 1 1 d . U . . .
C2 C 0.3810(8) 0.3733(6) 0.5891(5) 0.023(2) Uani 1 1 d . U . . .
H2 H 0.389792 0.497681 0.534427 0.028 Uiso 1 1 calc R U . . .
C3 C 0.3249(8) 0.4165(6) 0.6763(6) 0.027(2) Uani 1 1 d . U . . .
H3 H 0.291608 0.568858 0.676934 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3186(8) 0.2340(6) 0.7619(6) 0.027(2) Uani 1 1 d . U . . .
H4 H 0.282657 0.265955 0.821802 0.033 Uiso 1 1 calc R U . . .
C5 C 0.3642(8) 0.0062(6) 0.7605(5) 0.026(2) Uani 1 1 d . U . . .
H5 H 0.361030 -0.113973 0.820627 0.031 Uiso 1 1 calc R U . . .
C6 C 0.4147(8) -0.0442(6) 0.6701(5) 0.024(2) Uani 1 1 d . U . . .
H6 H 0.442626 -0.200379 0.665391 0.029 Uiso 1 1 calc R U . . .
N2 N 0.9870(7) 0.1077(5) 0.9789(5) 0.028(2) Uani 1 1 d . U . . .
C7 C 0.9218(8) 0.1258(6) 0.8359(6) 0.026(2) Uani 1 1 d . U . . .
C8 C 0.9116(8) -0.0664(6) 0.7455(5) 0.026(2) Uani 1 1 d . U . . .
H8 H 0.939202 -0.221475 0.779886 0.031 Uiso 1 1 calc R U . . .
C9 C 0.8606(8) -0.0246(6) 0.6059(6) 0.027(2) Uani 1 1 d . U . . .
H9 H 0.855426 -0.149857 0.544626 0.033 Uiso 1 1 calc R U . . .
C10 C 0.8169(8) 0.2038(6) 0.5567(5) 0.029(2) Uani 1 1 d . U . . .
H10 H 0.779991 0.231079 0.461651 0.035 Uiso 1 1 calc R U . . .
C11 C 0.8273(8) 0.3929(6) 0.6464(6) 0.028(2) Uani 1 1 d . U . . .
H11 H 0.798963 0.547415 0.611495 0.034 Uiso 1 1 calc R U . . .
C12 C 0.8791(8) 0.3549(6) 0.7870(6) 0.026(2) Uani 1 1 d . U . . .
H12 H 0.885213 0.481529 0.847808 0.031 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.032(6) 0.0313(16) 0.017(3) -0.0005(11) 0.012(4) 0.0014(17)
C1 0.032(7) 0.0303(15) 0.017(3) -0.0003(12) 0.012(4) 0.0007(19)
C2 0.026(7) 0.0288(15) 0.014(3) -0.0010(12) 0.007(4) -0.0018(18)
C3 0.033(7) 0.0287(16) 0.020(3) -0.0001(13) 0.013(4) 0.0011(19)
C4 0.033(7) 0.0326(16) 0.020(3) -0.0008(13) 0.014(4) 0.001(2)
C5 0.030(6) 0.0297(16) 0.018(3) 0.0018(13) 0.010(4) 0.0014(19)
C6 0.026(6) 0.0281(14) 0.019(3) -0.0003(13) 0.010(4) 0.0002(18)
N2 0.037(6) 0.0308(15) 0.021(3) 0.0012(12) 0.016(4) 0.0009(17)
C7 0.029(7) 0.0319(17) 0.018(3) 0.0022(13) 0.012(4) 0.0014(19)
C8 0.031(7) 0.0276(15) 0.022(3) -0.0003(13) 0.013(4) -0.0014(18)
C9 0.031(7) 0.0314(16) 0.021(3) -0.0012(14) 0.012(4) -0.002(2)
C10 0.033(7) 0.0349(16) 0.020(3) 0.0021(15) 0.012(4) 0.001(2)
C11 0.036(7) 0.0310(17) 0.020(3) 0.0037(13) 0.014(4) 0.0028(19)
C12 0.031(7) 0.0304(16) 0.016(3) 0.0008(13) 0.010(4) 0.0008(19)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.260(6) 3_656 ?
N1 C1 1.399(6) . ?
C1 C2 1.378(6) . ?
C1 C6 1.392(5) . ?
C2 C3 1.387(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.254(7) 3_757 ?
N2 C7 1.394(9) . ?
C7 C12 1.374(7) . ?
C7 C8 1.395(5) . ?
C8 C9 1.367(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.374(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.373(8) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 112.2(4) 3_656 . ?
C2 C1 C6 121.5(4) . . ?
C2 C1 N1 116.7(3) . . ?
C6 C1 N1 121.2(4) . . ?
C1 C2 C3 118.3(3) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 121.1(4) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 119.1(4) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N2 N2 C7 113.6(5) 3_757 . ?
C12 C7 N2 115.5(4) . . ?
C12 C7 C8 121.2(5) . . ?
N2 C7 C8 122.9(5) . . ?
C9 C8 C7 119.3(4) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 120.8(5) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 120.4(4) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C7 118.6(3) . . ?
C11 C12 H12 120.7 . . ?
C7 C12 H12 120.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -169.3(9) 3_656 . . . ?
N1 N1 C1 C6 19.6(13) 3_656 . . . ?
C6 C1 C2 C3 -2.2(13) . . . . ?
N1 C1 C2 C3 -173.3(7) . . . . ?
C1 C2 C3 C4 3.5(12) . . . . ?
C2 C3 C4 C5 -1.7(12) . . . . ?
C3 C4 C5 C6 -1.6(12) . . . . ?
C4 C5 C6 C1 2.9(12) . . . . ?
C2 C1 C6 C5 -1.0(13) . . . . ?
N1 C1 C6 C5 169.7(7) . . . . ?
N2 N2 C7 C12 172.6(8) 3_757 . . . ?
N2 N2 C7 C8 -14.7(12) 3_757 . . . ?
C12 C7 C8 C9 1.4(12) . . . . ?
N2 C7 C8 C9 -170.9(7) . . . . ?
C7 C8 C9 C10 -1.9(11) . . . . ?
C8 C9 C10 C11 2.0(11) . . . . ?
C9 C10 C11 C12 -1.5(12) . . . . ?
C10 C11 C12 C7 0.9(12) . . . . ?
N2 C7 C12 C11 171.9(7) . . . . ?
C8 C7 C12 C11 -0.9(12) . . . . ?


_shelx_res_file                  
;
TITL sample_0129_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 10:31:56 on 27-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  12.242001   5.474708  10.638917  90.0000 114.8362  90.0000
ZERR    4.00   0.019833   0.000573   0.006890   0.0000   0.1379   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
OMIT -6 -8 5
OMIT -5 -1 9
OMIT -1 -3 2
OMIT 12 2 -12
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.200000
BASF   0.42756
FVAR      30.55886
N1    1    0.490841    0.110986    0.508019    11.00000    0.03231    0.03131 =
         0.01676   -0.00046    0.01220    0.00137
C1    2    0.423453    0.141598    0.585420    11.00000    0.03213    0.03033 =
         0.01691   -0.00026    0.01239    0.00066
C2    2    0.381043    0.373344    0.589055    11.00000    0.02589    0.02877 =
         0.01378   -0.00100    0.00665   -0.00181
AFIX  43
H2    3    0.389792    0.497681    0.534427    11.00000   -1.20000
AFIX   0
C3    2    0.324944    0.416468    0.676312    11.00000    0.03258    0.02874 =
         0.02027   -0.00006    0.01293    0.00107
AFIX  43
H3    3    0.291608    0.568858    0.676934    11.00000   -1.20000
AFIX   0
C4    2    0.318574    0.234018    0.761932    11.00000    0.03307    0.03260 =
         0.01978   -0.00085    0.01446    0.00060
AFIX  43
H4    3    0.282657    0.265955    0.821802    11.00000   -1.20000
AFIX   0
C5    2    0.364222    0.006217    0.760485    11.00000    0.02962    0.02971 =
         0.01819    0.00183    0.01041    0.00136
AFIX  43
H5    3    0.361030   -0.113973    0.820627    11.00000   -1.20000
AFIX   0
C6    2    0.414670   -0.044213    0.670077    11.00000    0.02617    0.02814 =
         0.01880   -0.00030    0.01050    0.00016
AFIX  43
H6    3    0.442626   -0.200379    0.665391    11.00000   -1.20000
AFIX   0
N2    1    0.987038    0.107693    0.978942    11.00000    0.03733    0.03083 =
         0.02132    0.00119    0.01630    0.00092
C7    2    0.921772    0.125771    0.835876    11.00000    0.02908    0.03188 =
         0.01837    0.00216    0.01179    0.00143
C8    2    0.911576   -0.066414    0.745508    11.00000    0.03117    0.02763 =
         0.02165   -0.00033    0.01326   -0.00137
AFIX  43
H8    3    0.939202   -0.221475    0.779886    11.00000   -1.20000
AFIX   0
C9    2    0.860564   -0.024551    0.605886    11.00000    0.03053    0.03137 =
         0.02112   -0.00124    0.01185   -0.00200
AFIX  43
H9    3    0.855426   -0.149857    0.544626    11.00000   -1.20000
AFIX   0
C10   2    0.816945    0.203844    0.556686    11.00000    0.03311    0.03489 =
         0.01969    0.00214    0.01207    0.00126
AFIX  43
H10   3    0.779991    0.231079    0.461651    11.00000   -1.20000
AFIX   0
C11   2    0.827273    0.392946    0.646367    11.00000    0.03596    0.03099 =
         0.02035    0.00366    0.01374    0.00279
AFIX  43
H11   3    0.798963    0.547415    0.611495    11.00000   -1.20000
AFIX   0
C12   2    0.879109    0.354870    0.786957    11.00000    0.03107    0.03039 =
         0.01642    0.00083    0.00995    0.00085
AFIX  43
H12   3    0.885213    0.481529    0.847808    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0129_bn1 in P2(1)/c
REM wR2 = 0.2777, GooF = S = 1.116, Restrained GooF = 1.110 for all data
REM R1 = 0.0907 for 1818 Fo > 4sig(Fo) and 0.1057 for all 2408 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.2000      0.0000

REM Highest difference peak  0.421,  deepest hole -0.297,  1-sigma level  0.072
Q1    1   0.8144  0.0569  0.5507  11.00000  0.05    0.42
Q2    1   0.8747  0.0291  0.7801  11.00000  0.05    0.35
Q3    1   0.3792  0.3230  0.7427  11.00000  0.05    0.32
Q4    1   0.4011  0.1229  0.7956  11.00000  0.05    0.31
Q5    1   0.7311  0.3212  0.5690  11.00000  0.05    0.29
Q6    1   0.8851  0.2197  0.8009  11.00000  0.05    0.29
Q7    1   0.9370  0.3421  0.7319  11.00000  0.05    0.28
Q8    1   0.3620  0.0501  0.6076  11.00000  0.05    0.27
Q9    1   0.2684  0.3299  0.7024  11.00000  0.05    0.27
Q10   1   0.4356  0.2592  0.6256  11.00000  0.05    0.27
Q11   1   0.9407  0.0320  0.7959  11.00000  0.05    0.27
Q12   1   0.9385  0.2611  0.8411  11.00000  0.05    0.26
Q13   1   0.8845  0.2970  0.6173  11.00000  0.05    0.25
Q14   1   0.9047  0.4867  0.6448  11.00000  0.05    0.25
Q15   1   0.8656  0.1175  0.6012  11.00000  0.05    0.24
Q16   1   0.9570 -0.0157  0.9620  11.00000  0.05    0.23
Q17   1   1.0333 -0.1092  0.8376  11.00000  0.05    0.23
Q18   1   1.0496  0.1824  1.0402  11.00000  0.05    0.21
Q19   1   0.3882 -0.0996  0.7169  11.00000  0.05    0.21
Q20   1   0.4340  0.4248  0.6318  11.00000  0.05    0.21
;
_shelx_res_checksum              96540
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_11p5GPa
_database_code_depnum_ccdc_archive 'CCDC 2336570'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_11p5GPa         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.341 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT149_AZO_11p5GPa         
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.07 Degree
RESPONSE: Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree.
;
_vrf_PLAT411_AZO_11p5GPa         
;
PROBLEM: Short Inter H...H Contact  H2       ..H11      .       1.95 Ang.  
RESPONSE: Intermolecular distances are strongly shortened at high 
pressure and atoms approach closer to one another than at ambient 
conditions or low temperature.
;
_vrf_PLAT911_AZO_11p5GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        571 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3r (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-16
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   13.162(11)
_cell_length_b                   5.1734(3)
_cell_length_c                   10.885(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.15(7)
_cell_angle_gamma                90
_cell_volume                     681.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       11540000
_cell_measurement_reflns_used    528
_cell_measurement_theta_min      2.1570
_cell_measurement_theta_max      19.9530

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.57221
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         11540000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    0.50    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0337245889
_diffrn_orient_matrix_UB_12      0.0071544001
_diffrn_orient_matrix_UB_13      -0.0185291991
_diffrn_orient_matrix_UB_21      0.0029949439
_diffrn_orient_matrix_UB_22      0.0218950646
_diffrn_orient_matrix_UB_23      -0.0346116966
_diffrn_orient_matrix_UB_31      -0.0022451494
_diffrn_orient_matrix_UB_32      -0.0757464859
_diffrn_orient_matrix_UB_33      -0.0116697558
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2908
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.159
_diffrn_reflns_theta_max         21.675
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.197
_diffrn_measured_fraction_theta_full 0.341
_diffrn_reflns_Laue_measured_fraction_max 0.197
_diffrn_reflns_Laue_measured_fraction_full 0.341
_diffrn_reflns_point_group_measured_fraction_max 0.197
_diffrn_reflns_point_group_measured_fraction_full 0.341
_reflns_number_total             2908
_reflns_number_gt                2206
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
The BASF parameter was refined to 32.4%. 5 low-resolution reflections, that 
 were affected by beamstop, were removed from refinemet. Some other 
 reflections were removed as outliers. The atomic displacement parameters 
of atoms N2A, N2B and C7 were restraint with RIGU keyword in ShelXL input 
('enhanced rigid bond' restraint for all bonds in the connectivity list).
The anisotropic displacement parameters 
of the disordered nitrogen atoms N2A and N2B were restrained to 
similar behaviour using SIMU restraint.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1343P)²+0.0992P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2908
_refine_ls_number_parameters     138
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0731
_refine_ls_wR_factor_ref         0.2192
_refine_ls_wR_factor_gt          0.2059
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.067
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4898(5) 0.1165(5) 0.5068(3) 0.0214(18) Uani 1 1 d . . . . .
C1 C 0.4275(6) 0.1474(5) 0.5848(4) 0.021(2) Uani 1 1 d . . . . .
C2 C 0.3775(6) 0.3836(5) 0.5782(4) 0.021(2) Uani 1 1 d . . . . .
H2 H 0.382785 0.511238 0.520836 0.025 Uiso 1 1 calc R U . . .
C3 C 0.3195(6) 0.4289(6) 0.6573(4) 0.023(2) Uani 1 1 d . . . . .
H3 H 0.281448 0.583673 0.649029 0.028 Uiso 1 1 calc R U . . .
C4 C 0.3175(6) 0.2458(6) 0.7493(4) 0.022(2) Uani 1 1 d . . . . .
H4 H 0.279963 0.279173 0.804294 0.026 Uiso 1 1 calc R U . . .
C5 C 0.3717(6) 0.0138(5) 0.7587(4) 0.023(2) Uani 1 1 d . . . . .
H5 H 0.372877 -0.107096 0.822466 0.027 Uiso 1 1 calc R U . . .
C6 C 0.4238(6) -0.0399(5) 0.6743(4) 0.021(2) Uani 1 1 d . . . . .
H6 H 0.456392 -0.200546 0.677196 0.025 Uiso 1 1 calc R U . . .
N2A N 0.9637(14) 0.0804(9) 0.9741(12) 0.029(4) Uani 0.70(2) 1 d . U P A 1
N2B N 0.988(3) -0.096(2) 0.959(3) 0.029(4) Uani 0.30(2) 1 d . U P A 2
C7 C 0.9141(8) 0.0407(8) 0.8317(5) 0.033(3) Uani 1 1 d . . . . .
C8 C 0.9235(8) -0.1634(8) 0.7574(7) 0.040(3) Uani 1 1 d . . . . .
H8 H 0.962839 -0.310390 0.798582 0.048 Uiso 1 1 calc R U . . .
C9 C 0.8735(8) -0.1477(8) 0.6201(6) 0.038(3) Uani 1 1 d . . . . .
H9 H 0.879164 -0.284141 0.567498 0.046 Uiso 1 1 calc R U . . .
C10 C 0.8158(8) 0.0693(9) 0.5618(5) 0.037(3) Uani 1 1 d . . . . .
H10 H 0.781463 0.080105 0.469209 0.044 Uiso 1 1 calc R U . . .
C11 C 0.8083(8) 0.2722(7) 0.6395(6) 0.038(3) Uani 1 1 d . . . . .
H11 H 0.769692 0.420626 0.599309 0.045 Uiso 1 1 calc R U . . .
C12 C 0.8566(8) 0.2563(7) 0.7731(5) 0.036(3) Uani 1 1 d . . . . .
H12 H 0.850597 0.392637 0.825555 0.043 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.025(6) 0.0221(12) 0.020(2) -0.0013(9) 0.012(3) -0.0001(14)
C1 0.026(7) 0.0211(13) 0.020(2) -0.0013(10) 0.013(4) -0.0003(16)
C2 0.023(7) 0.0220(14) 0.020(2) 0.0009(10) 0.010(4) 0.0002(16)
C3 0.023(7) 0.0225(14) 0.025(2) -0.0013(11) 0.011(4) 0.0018(17)
C4 0.021(7) 0.0269(15) 0.021(2) -0.0016(11) 0.011(4) -0.0001(17)
C5 0.026(7) 0.0244(14) 0.019(2) 0.0017(10) 0.011(4) 0.0004(17)
C6 0.024(6) 0.0198(12) 0.022(2) -0.0003(10) 0.012(4) -0.0005(16)
N2A 0.037(11) 0.033(2) 0.022(5) 0.002(2) 0.016(7) 0.007(3)
N2B 0.035(14) 0.037(5) 0.020(7) 0.000(4) 0.016(9) -0.004(6)
C7 0.018(9) 0.057(2) 0.020(3) 0.0076(16) 0.003(5) -0.009(3)
C8 0.028(9) 0.035(2) 0.061(4) 0.0115(18) 0.020(6) 0.003(2)
C9 0.021(10) 0.046(2) 0.053(4) -0.020(2) 0.022(6) -0.009(3)
C10 0.027(11) 0.062(3) 0.022(3) 0.0018(17) 0.011(6) -0.009(3)
C11 0.030(9) 0.038(2) 0.051(4) 0.0157(18) 0.023(6) 0.008(3)
C12 0.041(9) 0.0382(19) 0.042(3) -0.0101(15) 0.029(5) -0.012(2)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.256(5) 3_656 ?
N1 C1 1.401(5) . ?
C1 C2 1.376(5) . ?
C1 C6 1.389(4) . ?
C2 C3 1.377(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2A N2A 1.22(2) 3_757 ?
N2A C7 1.440(14) . ?
N2B N2B 1.29(4) 3_757 ?
N2B C7 1.52(3) . ?
C7 C12 1.358(9) . ?
C7 C8 1.366(6) . ?
C8 C9 1.378(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.364(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.341(9) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 112.6(3) 3_656 . ?
C2 C1 C6 120.5(3) . . ?
C2 C1 N1 116.8(2) . . ?
C6 C1 N1 122.4(4) . . ?
C1 C2 C3 119.3(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 120.5(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2A N2A C7 109.8(8) 3_757 . ?
N2B N2B C7 100(2) 3_757 . ?
C12 C7 C8 121.3(5) . . ?
C12 C7 N2A 108.7(4) . . ?
C8 C7 N2A 129.8(7) . . ?
C12 C7 N2B 148.2(7) . . ?
C8 C7 N2B 90.4(8) . . ?
C7 C8 C9 118.8(6) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C8 119.6(4) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 120.2(5) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.1(5) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C7 119.9(3) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -164.1(7) 3_656 . . . ?
N1 N1 C1 C6 21.7(10) 3_656 . . . ?
C6 C1 C2 C3 -2.7(9) . . . . ?
N1 C1 C2 C3 -177.0(6) . . . . ?
C1 C2 C3 C4 4.3(10) . . . . ?
C2 C3 C4 C5 -1.8(10) . . . . ?
C3 C4 C5 C6 -2.4(10) . . . . ?
C4 C5 C6 C1 3.9(10) . . . . ?
C2 C1 C6 C5 -1.3(9) . . . . ?
N1 C1 C6 C5 172.6(6) . . . . ?
N2A N2A C7 C12 -163.8(11) 3_757 . . . ?
N2A N2A C7 C8 12.3(18) 3_757 . . . ?
N2B N2B C7 C12 -11(4) 3_757 . . . ?
N2B N2B C7 C8 165(2) 3_757 . . . ?
C12 C7 C8 C9 0.3(12) . . . . ?
N2A C7 C8 C9 -175.4(9) . . . . ?
N2B C7 C8 C9 -177.0(12) . . . . ?
C7 C8 C9 C10 -0.3(12) . . . . ?
C8 C9 C10 C11 0.6(11) . . . . ?
C9 C10 C11 C12 -0.8(11) . . . . ?
C10 C11 C12 C7 0.8(12) . . . . ?
C8 C7 C12 C11 -0.6(11) . . . . ?
N2A C7 C12 C11 175.9(8) . . . . ?
N2B C7 C12 C11 174(2) . . . . ?


_shelx_res_file                  
;
TITL sample_0105_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 22:55:32 on 24-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  13.162213   5.173382  10.885030  90.0000 113.1534  90.0000
ZERR    4.00   0.011073   0.000315   0.003325   0.0000   0.0671   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
OMIT 3 1 -6
OMIT -3 -1 6
OMIT 0 2 -1
OMIT 2 -1 -1
OMIT -2 1 1
OMIT -1 -2 2
OMIT -1 1 1
OMIT 1 1 -1
SIMU 0.005 0.01 2 N2A N2B
rigU 0.005 0.01 N2A N2B C7
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
REM ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.134300    0.099200
BASF   0.32381
FVAR      25.58015   0.70346
N1    1    0.489774    0.116484    0.506805    11.00000    0.02522    0.02211 =
         0.01968   -0.00135    0.01191   -0.00010
C1    2    0.427524    0.147403    0.584764    11.00000    0.02560    0.02110 =
         0.02018   -0.00128    0.01333   -0.00034
C2    2    0.377501    0.383557    0.578180    11.00000    0.02292    0.02204 =
         0.01974    0.00086    0.00995    0.00020
AFIX  43
H2    3    0.382785    0.511238    0.520836    11.00000   -1.20000
AFIX   0
C3    2    0.319545    0.428918    0.657347    11.00000    0.02317    0.02252 =
         0.02499   -0.00130    0.01150    0.00182
AFIX  43
H3    3    0.281448    0.583673    0.649029    11.00000   -1.20000
AFIX   0
C4    2    0.317525    0.245827    0.749321    11.00000    0.02096    0.02692 =
         0.02130   -0.00164    0.01148   -0.00011
AFIX  43
H4    3    0.279963    0.279173    0.804294    11.00000   -1.20000
AFIX   0
C5    2    0.371672    0.013766    0.758661    11.00000    0.02628    0.02438 =
         0.01917    0.00169    0.01096    0.00035
AFIX  43
H5    3    0.372877   -0.107096    0.822466    11.00000   -1.20000
AFIX   0
C6    2    0.423806   -0.039931    0.674349    11.00000    0.02407    0.01978 =
         0.02198   -0.00034    0.01195   -0.00046
AFIX  43
H6    3    0.456392   -0.200546    0.677196    11.00000   -1.20000
AFIX   0
PART 1 21.
N2A   1    0.963694    0.080447    0.974137    21.00000    0.03650    0.03345 =
         0.02168    0.00241    0.01571    0.00668
PART 2 -21.
N2B   1    0.987769   -0.095684    0.958839   -21.00000    0.03528    0.03716 =
         0.02028   -0.00002    0.01611   -0.00414
PART 0
C7    2    0.914119    0.040717    0.831747    11.00000    0.01801    0.05712 =
         0.01982    0.00764    0.00290   -0.00942
C8    2    0.923486   -0.163428    0.757363    11.00000    0.02790    0.03453 =
         0.06067    0.01153    0.02025    0.00275
AFIX  43
H8    3    0.962839   -0.310390    0.798582    11.00000   -1.20000
AFIX   0
C9    2    0.873547   -0.147659    0.620081    11.00000    0.02115    0.04602 =
         0.05343   -0.02028    0.02199   -0.00945
AFIX  43
H9    3    0.879164   -0.284141    0.567498    11.00000   -1.20000
AFIX   0
C10   2    0.815839    0.069278    0.561793    11.00000    0.02656    0.06235 =
         0.02208    0.00178    0.01067   -0.00908
AFIX  43
H10   3    0.781463    0.080105    0.469209    11.00000   -1.20000
AFIX   0
C11   2    0.808311    0.272155    0.639506    11.00000    0.03020    0.03791 =
         0.05149    0.01574    0.02317    0.00813
AFIX  43
H11   3    0.769692    0.420626    0.599309    11.00000   -1.20000
AFIX   0
C12   2    0.856557    0.256250    0.773125    11.00000    0.04070    0.03824 =
         0.04167   -0.01010    0.02940   -0.01157
AFIX  43
H12   3    0.850597    0.392637    0.825555    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0105_bn1 in P2(1)/c
REM wR2 = 0.2192, GooF = S = 1.103, Restrained GooF = 1.102 for all data
REM R1 = 0.0731 for 2206 Fo > 4sig(Fo) and 0.0888 for all 2908 data
REM 138 parameters refined using 12 restraints

END

WGHT      0.1343      0.0992

REM Highest difference peak  0.420,  deepest hole -0.367,  1-sigma level  0.067
Q1    1   0.3099  0.1110  0.7408  11.00000  0.05    0.33
Q2    1   0.5000  0.0000  0.5000  10.50000  0.05    0.33
Q3    1   0.3887  0.2423  0.5819  11.00000  0.05    0.31
Q4    1   0.9142 -0.2293  0.7085  11.00000  0.05    0.30
Q5    1   0.3337  0.3382  0.7164  11.00000  0.05    0.28
Q6    1   0.4475  0.0664  0.6491  11.00000  0.05    0.27
Q7    1   0.8150  0.2209  0.7003  11.00000  0.05    0.26
Q8    1   0.9322  0.1728  0.9890  11.00000  0.05    0.24
Q9    1   0.9159  0.1498  0.8134  11.00000  0.05    0.23
Q10   1   0.3643 -0.0188  0.6876  11.00000  0.05    0.23
Q11   1   0.2462  0.1911  0.6935  11.00000  0.05    0.21
Q12   1   0.3739  0.4618  0.6182  11.00000  0.05    0.20
Q13   1   0.7504  0.1842  0.4594  11.00000  0.05    0.19
Q14   1   0.2332  0.2734  0.5958  11.00000  0.05    0.19
Q15   1   0.4487  0.0777  0.5419  11.00000  0.05    0.18
Q16   1   0.8716 -0.1374  0.6773  11.00000  0.05    0.18
Q17   1   0.7916 -0.3215  0.5884  11.00000  0.05    0.18
Q18   1   0.7892  0.1645  0.5921  11.00000  0.05    0.18
Q19   1   0.3640  0.4467  0.7059  11.00000  0.05    0.17
Q20   1   0.4853 -0.3773  0.7710  11.00000  0.05    0.17
;
_shelx_res_checksum              75416
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_1GPa
_database_code_depnum_ccdc_archive 'CCDC 2336588'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_1GPa            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.351 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT911_AZO_1GPa            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        691 Report
RESPONSE:  Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3q (K.Radacki, 2005-22)'
_audit_creation_date             2023-03-15
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   14.710(10)
_cell_length_b                   5.5772(3)
_cell_length_c                   11.759(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.39(5)
_cell_angle_gamma                90
_cell_volume                     892.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       1015000
_cell_measurement_reflns_used    461
_cell_measurement_theta_min      2.1560
_cell_measurement_theta_max      20.3070

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.58706
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 Crystals were grown from saturated solution. For data collection the crystal 
 was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         1015000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    0.50    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.0299201000
_diffrn_orient_matrix_UB_12      0.0062613000
_diffrn_orient_matrix_UB_13      0.0176273000
_diffrn_orient_matrix_UB_21      -0.0035030000
_diffrn_orient_matrix_UB_22      0.0196118000
_diffrn_orient_matrix_UB_23      0.0316687000
_diffrn_orient_matrix_UB_31      0.0016704000
_diffrn_orient_matrix_UB_32      -0.0705464000
_diffrn_orient_matrix_UB_33      0.0103692000
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            4288
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.999
_diffrn_reflns_theta_max         20.999
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.227
_diffrn_measured_fraction_theta_full 0.351
_diffrn_reflns_Laue_measured_fraction_max 0.227
_diffrn_reflns_Laue_measured_fraction_full 0.351
_diffrn_reflns_point_group_measured_fraction_max 0.227
_diffrn_reflns_point_group_measured_fraction_full 0.351
_reflns_number_total             4288
_reflns_number_gt                3223
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
The BASF parameter was refined to 43.7%. The anisotropic displacement 
parameters of the disordered nitrogen atoms N2A and N2B were restrained to 
similar behaviour using SIMU restraint. The anisotropic displacement 
parameters of all atoms were restrained to isotropic behqaviour using ISOR 
restraint.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1045P)²] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4288
_refine_ls_number_parameters     138
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1688
_refine_ls_wR_factor_gt          0.1580
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.040
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4891(3) 0.1067(3) 0.5049(2) 0.0308(10) Uani 1 1 d . U . . .
C1 C 0.4317(3) 0.1389(3) 0.5774(2) 0.0274(11) Uani 1 1 d . U . . .
C2 C 0.3823(3) 0.3561(3) 0.5641(2) 0.0319(12) Uani 1 1 d . U . . .
H2 H 0.387960 0.471181 0.509910 0.038 Uiso 1 1 calc R U . . .
C3 C 0.3251(3) 0.4014(3) 0.6313(3) 0.0363(13) Uani 1 1 d . U . . .
H3 H 0.290221 0.544357 0.620192 0.044 Uiso 1 1 calc R U . . .
C4 C 0.3195(3) 0.2327(4) 0.7159(3) 0.0358(13) Uani 1 1 d . U . . .
H4 H 0.281526 0.263475 0.761917 0.043 Uiso 1 1 calc R U . . .
C5 C 0.3707(3) 0.0190(4) 0.7309(3) 0.0338(12) Uani 1 1 d . U . . .
H5 H 0.367656 -0.091995 0.788375 0.041 Uiso 1 1 calc R U . . .
C6 C 0.4263(3) -0.0320(3) 0.6619(2) 0.0286(11) Uani 1 1 d . U . . .
H6 H 0.459556 -0.177138 0.671423 0.034 Uiso 1 1 calc R U . . .
N2A N 0.9679(4) 0.0769(3) 0.9762(4) 0.0392(15) Uani 0.925(10) 1 d . U P A 1
N2B N 0.990(5) -0.094(5) 0.956(5) 0.040(4) Uani 0.075(10) 1 d . U P A 2
C7 C 0.9186(3) 0.0534(4) 0.8464(3) 0.0360(14) Uani 1 1 d . U . . .
C8 C 0.9282(4) -0.1405(4) 0.7759(3) 0.0404(14) Uani 1 1 d . U . . .
H8 H 0.969158 -0.268704 0.813024 0.048 Uiso 1 1 calc R U . . .
C9 C 0.8757(4) -0.1376(4) 0.6504(3) 0.0456(17) Uani 1 1 d . U . . .
H9 H 0.880795 -0.266262 0.602910 0.055 Uiso 1 1 calc R U . . .
C10 C 0.8157(4) 0.0532(5) 0.5944(3) 0.0421(16) Uani 1 1 d . U . . .
H10 H 0.780946 0.053478 0.509704 0.050 Uiso 1 1 calc R U . . .
C11 C 0.8075(4) 0.2453(4) 0.6653(3) 0.0467(17) Uani 1 1 d . U . . .
H11 H 0.767851 0.375456 0.627972 0.056 Uiso 1 1 calc R U . . .
C12 C 0.8576(4) 0.2430(4) 0.7895(3) 0.0425(15) Uani 1 1 d . U . . .
H12 H 0.850778 0.370444 0.836571 0.051 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.036(3) 0.0290(7) 0.0323(13) -0.0002(6) 0.019(2) 0.0019(8)
C1 0.031(3) 0.0266(8) 0.0265(14) -0.0019(6) 0.013(2) 0.0004(9)
C2 0.036(4) 0.0287(9) 0.0323(16) 0.0018(7) 0.014(2) 0.0039(10)
C3 0.039(4) 0.0311(9) 0.0434(18) -0.0034(8) 0.020(3) 0.0051(11)
C4 0.036(4) 0.0399(10) 0.0368(18) -0.0056(8) 0.020(3) -0.0001(11)
C5 0.037(4) 0.0375(10) 0.0314(17) 0.0003(7) 0.018(2) -0.0028(11)
C6 0.030(4) 0.0275(8) 0.0295(15) 0.0004(6) 0.013(2) 0.0015(9)
N2A 0.044(4) 0.0411(11) 0.033(3) 0.0027(9) 0.016(3) 0.0077(12)
N2B 0.045(7) 0.044(6) 0.032(6) 0.003(5) 0.016(7) 0.006(6)
C7 0.034(5) 0.0434(11) 0.0330(18) 0.0045(8) 0.016(3) 0.0001(12)
C8 0.039(5) 0.0395(11) 0.044(2) 0.0027(9) 0.017(3) 0.0026(12)
C9 0.048(5) 0.0479(13) 0.045(2) -0.0101(10) 0.023(3) -0.0049(14)
C10 0.033(5) 0.0605(15) 0.030(2) 0.0023(10) 0.009(3) -0.0035(16)
C11 0.048(5) 0.0477(13) 0.046(2) 0.0117(10) 0.020(3) 0.0097(15)
C12 0.049(5) 0.0426(11) 0.039(2) 0.0010(9) 0.021(3) 0.0032(13)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.250(3) 3_656 ?
N1 C1 1.421(3) . ?
C1 C2 1.390(3) . ?
C1 C6 1.400(2) . ?
C2 C3 1.380(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2A N2A 1.241(9) 3_757 ?
N2A C7 1.424(6) . ?
N2B N2B 1.43(9) 3_757 ?
N2B C7 1.55(6) . ?
C7 C12 1.383(5) . ?
C7 C8 1.402(3) . ?
C8 C9 1.381(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.391(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.362(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 114.1(2) 3_656 . ?
C2 C1 C6 120.3(2) . . ?
C2 C1 N1 116.53(16) . . ?
C6 C1 N1 123.1(2) . . ?
C3 C2 C1 120.09(17) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C6 C5 C4 121.09(18) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N2A N2A C7 114.2(4) 3_757 . ?
N2B N2B C7 96(4) 3_757 . ?
C12 C7 C8 119.7(3) . . ?
C12 C7 N2A 114.8(2) . . ?
C8 C7 N2A 125.4(3) . . ?
C12 C7 N2B 156.5(14) . . ?
C8 C7 N2B 83.7(14) . . ?
C9 C8 C7 118.8(3) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C10 C9 C8 121.0(2) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 120.8(2) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -162.5(4) 3_656 . . . ?
N1 N1 C1 C6 19.8(6) 3_656 . . . ?
C6 C1 C2 C3 -2.2(6) . . . . ?
N1 C1 C2 C3 -180.0(3) . . . . ?
C1 C2 C3 C4 2.3(6) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
C3 C4 C5 C6 -1.1(6) . . . . ?
C4 C5 C6 C1 1.2(5) . . . . ?
C2 C1 C6 C5 0.4(5) . . . . ?
N1 C1 C6 C5 178.0(3) . . . . ?
N2A N2A C7 C12 -170.6(4) 3_757 . . . ?
N2A N2A C7 C8 8.9(7) 3_757 . . . ?
N2B N2B C7 C12 -13(9) 3_757 . . . ?
N2B N2B C7 C8 169(5) 3_757 . . . ?
C12 C7 C8 C9 -0.3(6) . . . . ?
N2A C7 C8 C9 -179.8(4) . . . . ?
N2B C7 C8 C9 179(2) . . . . ?
C7 C8 C9 C10 0.9(6) . . . . ?
C8 C9 C10 C11 -0.3(6) . . . . ?
C9 C10 C11 C12 -0.8(6) . . . . ?
C10 C11 C12 C7 1.3(6) . . . . ?
C8 C7 C12 C11 -0.8(6) . . . . ?
N2A C7 C12 C11 178.8(4) . . . . ?
N2B C7 C12 C11 -178(5) . . . . ?


_shelx_res_file                  
;
TITL sample_0021_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 19:41:27 on 23-Feb-2023
REM P2(1)/c (#14 in standard setting)
CELL 0.41000  14.710118   5.577211  11.758747  90.0000 112.3880  90.0000
ZERR    4.00   0.010031   0.000250   0.002933   0.0000   0.0542   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
OMIT -1 -1 1
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.03
FMAP 2
PLAN 20
WGHT    0.104500
BASF   0.43686
FVAR      22.32195   0.92457
N1    1    0.489077    0.106714    0.504931    11.00000    0.03608    0.02895 =
         0.03232   -0.00018    0.01852    0.00187
C1    2    0.431659    0.138873    0.577375    11.00000    0.03096    0.02657 =
         0.02650   -0.00188    0.01292    0.00042
C2    2    0.382346    0.356150    0.564124    11.00000    0.03609    0.02870 =
         0.03226    0.00180    0.01450    0.00390
AFIX  43
H2    3    0.387960    0.471181    0.509910    11.00000   -1.20000
AFIX   0
C3    2    0.325072    0.401359    0.631321    11.00000    0.03853    0.03110 =
         0.04342   -0.00341    0.02031    0.00510
AFIX  43
H3    3    0.290221    0.544357    0.620192    11.00000   -1.20000
AFIX   0
C4    2    0.319476    0.232684    0.715851    11.00000    0.03601    0.03986 =
         0.03679   -0.00555    0.01992   -0.00007
AFIX  43
H4    3    0.281526    0.263475    0.761917    11.00000   -1.20000
AFIX   0
C5    2    0.370687    0.019044    0.730919    11.00000    0.03687    0.03750 =
         0.03143    0.00031    0.01780   -0.00285
AFIX  43
H5    3    0.367656   -0.091995    0.788375    11.00000   -1.20000
AFIX   0
C6    2    0.426326   -0.032007    0.661870    11.00000    0.03012    0.02747 =
         0.02953    0.00043    0.01291    0.00147
AFIX  43
H6    3    0.459556   -0.177138    0.671423    11.00000   -1.20000
AFIX   0
SIMU 0.003 N2A N2B
PART 1 21.
N2A   1    0.967852    0.076900    0.976170    21.00000    0.04399    0.04107 =
         0.03346    0.00275    0.01566    0.00771
PART 2 -21.
N2B   1    0.990239   -0.094053    0.955596   -21.00000    0.04466    0.04358 =
         0.03231    0.00313    0.01551    0.00591
PART 0
C7    2    0.918601    0.053392    0.846426    11.00000    0.03400    0.04343 =
         0.03302    0.00453    0.01562    0.00014
C8    2    0.928178   -0.140460    0.775934    11.00000    0.03856    0.03951 =
         0.04393    0.00265    0.01668    0.00261
AFIX  43
H8    3    0.969158   -0.268704    0.813024    11.00000   -1.20000
AFIX   0
C9    2    0.875651   -0.137558    0.650393    11.00000    0.04829    0.04789 =
         0.04539   -0.01011    0.02325   -0.00488
AFIX  43
H9    3    0.880795   -0.266262    0.602910    11.00000   -1.20000
AFIX   0
C10   2    0.815697    0.053246    0.594375    11.00000    0.03343    0.06048 =
         0.02977    0.00229    0.00925   -0.00352
AFIX  43
H10   3    0.780946    0.053478    0.509704    11.00000   -1.20000
AFIX   0
C11   2    0.807534    0.245346    0.665320    11.00000    0.04820    0.04765 =
         0.04599    0.01165    0.01975    0.00972
AFIX  43
H11   3    0.767851    0.375456    0.627972    11.00000   -1.20000
AFIX   0
C12   2    0.857643    0.242962    0.789482    11.00000    0.04934    0.04263 =
         0.03899    0.00105    0.02074    0.00317
AFIX  43
H12   3    0.850778    0.370444    0.836571    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0021_bn1 in P2(1)/c
REM wR2 = 0.1688, GooF = S = 1.077, Restrained GooF = 1.065 for all data
REM R1 = 0.0554 for 3223 Fo > 4sig(Fo) and 0.0718 for all 4288 data
REM 138 parameters refined using 96 restraints

END

WGHT      0.1045      0.0000

REM Highest difference peak  0.265,  deepest hole -0.185,  1-sigma level  0.040
Q1    1   0.9307 -0.0498  0.8298  11.00000  0.05    0.27
Q2    1   0.3995 -0.0084  0.6990  11.00000  0.05    0.25
Q3    1   0.4214  0.0446  0.6067  11.00000  0.05    0.23
Q4    1   0.3635  0.3596  0.6069  11.00000  0.05    0.21
Q5    1   0.4321  0.2621  0.5855  11.00000  0.05    0.18
Q6    1   0.3307  0.1150  0.7096  11.00000  0.05    0.17
Q7    1   0.3175  0.3143  0.6635  11.00000  0.05    0.16
Q8    1   0.8616 -0.1664  0.7008  11.00000  0.05    0.15
Q9    1   0.5046  0.2155  0.4773  11.00000  0.05    0.14
Q10   1   0.8175  0.1482  0.6290  11.00000  0.05    0.14
Q11   1   0.4575  0.1163  0.5417  11.00000  0.05    0.13
Q12   1   0.8708  0.1318  0.8067  11.00000  0.05    0.12
Q13   1   0.8812 -0.0967  0.7788  11.00000  0.05    0.12
Q14   1   0.9142 -0.2925  0.9401  11.00000  0.05    0.12
Q15   1   0.7094 -0.0173  0.5833  11.00000  0.05    0.11
Q16   1   0.8178 -0.0593  0.6230  11.00000  0.05    0.11
Q17   1   0.3452  0.5674  0.8544  11.00000  0.05    0.11
Q18   1   0.9285  0.3553  0.8393  11.00000  0.05    0.11
Q19   1   0.2193  0.5279  0.5529  11.00000  0.05    0.11
Q20   1   0.7877  0.4038  0.8905  11.00000  0.05    0.10
;
_shelx_res_checksum              1519
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_15p6GPa
_database_code_depnum_ccdc_archive 'CCDC 2336579'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_15p6GPa         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.347 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT411_AZO_15p6GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.73 Ang.  
RESPONSE: Intermolecular distances are strongly shortened at high 
pressure and atoms approach closer to one another than at ambient 
conditions or low temperature.
;
_vrf_PLAT149_AZO_15p6GPa         
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.11 Degree
RESPONSE: Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree.
;
_vrf_PLAT911_AZO_15p6GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        600 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3s (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-16
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   12.162(16)
_cell_length_b                   5.4949(4)
_cell_length_c                   10.602(6)
_cell_angle_alpha                90
_cell_angle_beta                 115.15(11)
_cell_angle_gamma                90
_cell_volume                     641.4(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       15550000
_cell_measurement_reflns_used    538
_cell_measurement_theta_min      2.2100
_cell_measurement_theta_max      20.0640

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.887
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.20895
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         15550000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    1.00    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0370736166
_diffrn_orient_matrix_UB_12      0.0066880961
_diffrn_orient_matrix_UB_13      -0.0204807893
_diffrn_orient_matrix_UB_21      0.0031672759
_diffrn_orient_matrix_UB_22      0.0221250022
_diffrn_orient_matrix_UB_23      -0.0352370163
_diffrn_orient_matrix_UB_31      -0.0024127411
_diffrn_orient_matrix_UB_32      -0.0708898083
_diffrn_orient_matrix_UB_33      -0.0128113542
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2608
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.216
_diffrn_reflns_theta_max         21.412
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.207
_diffrn_measured_fraction_theta_full 0.347
_diffrn_reflns_Laue_measured_fraction_max 0.207
_diffrn_reflns_Laue_measured_fraction_full 0.347
_diffrn_reflns_point_group_measured_fraction_max 0.207
_diffrn_reflns_point_group_measured_fraction_full 0.347
_reflns_number_total             2608
_reflns_number_gt                2079
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
 Datasets from multiple crystals were merged in shelXL and their reflections 
 were scaled using HKLF 5 with BASF. The BASF parameter was refined to 40.9%. 
 Some reflections were removed from refinement as outliers. 
 The Uii displacement parameters of all atoms were restrained with ISOR 
 keyword to approximate isotropic behavior.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1785P)²] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2608
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0817
_refine_ls_wR_factor_ref         0.2476
_refine_ls_wR_factor_gt          0.2356
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.130
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.069
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4905(6) 0.1104(4) 0.5081(4) 0.0237(18) Uani 1 1 d . U . . .
C1 C 0.4226(7) 0.1421(5) 0.5853(5) 0.0236(19) Uani 1 1 d . U . . .
C2 C 0.3807(7) 0.3732(5) 0.5897(5) 0.023(2) Uani 1 1 d . U . . .
H2 H 0.389396 0.497405 0.535080 0.028 Uiso 1 1 calc R U . . .
C3 C 0.3253(7) 0.4153(5) 0.6778(5) 0.025(2) Uani 1 1 d . U . . .
H3 H 0.292585 0.567598 0.679440 0.030 Uiso 1 1 calc R U . . .
C4 C 0.3184(7) 0.2332(5) 0.7628(5) 0.024(2) Uani 1 1 d . U . . .
H4 H 0.282769 0.265044 0.823157 0.029 Uiso 1 1 calc R U . . .
C5 C 0.3632(7) 0.0052(5) 0.7602(5) 0.024(2) Uani 1 1 d . U . . .
H5 H 0.359897 -0.115174 0.820222 0.029 Uiso 1 1 calc R U . . .
C6 C 0.4128(7) -0.0441(5) 0.6688(5) 0.0225(19) Uani 1 1 d . U . . .
H6 H 0.439581 -0.200213 0.662507 0.027 Uiso 1 1 calc R U . . .
N2 N 0.9884(6) 0.1085(4) 0.9796(4) 0.0243(19) Uani 1 1 d . U . . .
C7 C 0.9223(7) 0.1288(5) 0.8359(5) 0.023(2) Uani 1 1 d . U . . .
C8 C 0.9110(7) -0.0627(5) 0.7450(5) 0.024(2) Uani 1 1 d . U . . .
H8 H 0.938731 -0.217477 0.779430 0.029 Uiso 1 1 calc R U . . .
C9 C 0.8584(7) -0.0199(5) 0.6038(5) 0.025(2) Uani 1 1 d . U . . .
H9 H 0.850812 -0.145012 0.541575 0.030 Uiso 1 1 calc R U . . .
C10 C 0.8174(7) 0.2094(5) 0.5559(5) 0.026(2) Uani 1 1 d . U . . .
H10 H 0.781260 0.238681 0.460439 0.031 Uiso 1 1 calc R U . . .
C11 C 0.8288(8) 0.3970(5) 0.6465(5) 0.027(2) Uani 1 1 d . U . . .
H11 H 0.801255 0.551611 0.611827 0.032 Uiso 1 1 calc R U . . .
C12 C 0.8807(7) 0.3578(5) 0.7878(5) 0.025(2) Uani 1 1 d . U . . .
H12 H 0.887367 0.483565 0.849411 0.030 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.030(6) 0.0265(13) 0.017(2) -0.0004(9) 0.012(4) 0.0015(14)
C1 0.030(6) 0.0273(13) 0.017(2) -0.0001(11) 0.013(4) 0.0006(17)
C2 0.028(7) 0.0276(14) 0.015(3) -0.0005(11) 0.009(4) -0.0013(17)
C3 0.033(6) 0.0250(13) 0.020(3) -0.0008(11) 0.014(4) 0.0000(16)
C4 0.029(6) 0.0283(13) 0.019(3) 0.0003(11) 0.014(4) 0.0018(17)
C5 0.028(6) 0.0273(14) 0.017(3) 0.0018(11) 0.009(4) 0.0014(17)
C6 0.024(6) 0.0263(13) 0.018(2) -0.0010(11) 0.010(4) -0.0010(17)
N2 0.029(6) 0.0284(14) 0.017(2) 0.0015(10) 0.011(4) 0.0009(15)
C7 0.026(6) 0.0289(14) 0.016(3) 0.0016(11) 0.010(4) 0.0003(17)
C8 0.030(6) 0.0242(13) 0.020(3) 0.0006(11) 0.012(4) -0.0003(16)
C9 0.028(7) 0.0281(14) 0.020(3) -0.0016(12) 0.011(4) -0.0021(18)
C10 0.030(7) 0.0310(14) 0.018(3) 0.0018(13) 0.011(4) 0.0005(19)
C11 0.036(7) 0.0277(14) 0.021(3) 0.0034(12) 0.015(4) 0.0032(18)
C12 0.032(6) 0.0270(14) 0.017(3) 0.0015(12) 0.011(4) 0.0013(18)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.260(5) 3_656 ?
N1 C1 1.400(6) . ?
C1 C2 1.376(5) . ?
C1 C6 1.390(4) . ?
C2 C3 1.384(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.259(6) 3_757 ?
N2 C7 1.393(7) . ?
C7 C12 1.372(6) . ?
C7 C8 1.394(4) . ?
C8 C9 1.376(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.373(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 112.7(4) 3_656 . ?
C2 C1 C6 121.6(3) . . ?
C2 C1 N1 117.0(3) . . ?
C6 C1 N1 120.8(4) . . ?
C1 C2 C3 118.1(3) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N2 N2 C7 113.1(4) 3_757 . ?
C12 C7 N2 115.5(3) . . ?
C12 C7 C8 121.6(4) . . ?
N2 C7 C8 122.5(4) . . ?
C9 C8 C7 119.1(4) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 119.2(3) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 121.1(4) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 120.5(4) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C7 C12 C11 118.4(3) . . ?
C7 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -169.9(8) 3_656 . . . ?
N1 N1 C1 C6 18.7(11) 3_656 . . . ?
C6 C1 C2 C3 -1.5(11) . . . . ?
N1 C1 C2 C3 -172.8(6) . . . . ?
C1 C2 C3 C4 3.2(11) . . . . ?
C2 C3 C4 C5 -1.6(11) . . . . ?
C3 C4 C5 C6 -1.8(11) . . . . ?
C4 C5 C6 C1 3.4(11) . . . . ?
C2 C1 C6 C5 -1.8(12) . . . . ?
N1 C1 C6 C5 169.2(6) . . . . ?
N2 N2 C7 C12 171.7(7) 3_757 . . . ?
N2 N2 C7 C8 -15.7(11) 3_757 . . . ?
C12 C7 C8 C9 0.9(10) . . . . ?
N2 C7 C8 C9 -171.3(6) . . . . ?
C7 C8 C9 C10 -0.6(10) . . . . ?
C8 C9 C10 C11 0.5(10) . . . . ?
C9 C10 C11 C12 -0.7(11) . . . . ?
N2 C7 C12 C11 171.5(6) . . . . ?
C8 C7 C12 C11 -1.1(11) . . . . ?
C10 C11 C12 C7 1.0(11) . . . . ?


_shelx_res_file                  
;
TITL sample_0136_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 10:38:34 on 27-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  12.162183   5.494890  10.602088  90.0000 115.1521  90.0000
ZERR    4.00   0.015613   0.000411   0.005553   0.0000   0.1108   0.0000
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
OMIT 3 -5 -12
OMIT -7 -7 4
OMIT 12 2 -12
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.178500
BASF   0.40903
FVAR      30.20700
N1    1    0.490547    0.110405    0.508069    11.00000    0.03024    0.02653 =
         0.01678   -0.00036    0.01234    0.00146
C1    2    0.422629    0.142081    0.585339    11.00000    0.02984    0.02734 =
         0.01657   -0.00010    0.01278    0.00061
C2    2    0.380720    0.373164    0.589731    11.00000    0.02801    0.02760 =
         0.01462   -0.00047    0.00937   -0.00128
AFIX  43
H2    3    0.389396    0.497405    0.535080    11.00000   -1.20000
AFIX   0
C3    2    0.325303    0.415293    0.677808    11.00000    0.03270    0.02503 =
         0.01964   -0.00084    0.01377    0.00003
AFIX  43
H3    3    0.292585    0.567598    0.679440    11.00000   -1.20000
AFIX   0
C4    2    0.318439    0.233174    0.762769    11.00000    0.02938    0.02826 =
         0.01869    0.00030    0.01364    0.00179
AFIX  43
H4    3    0.282769    0.265044    0.823157    11.00000   -1.20000
AFIX   0
C5    2    0.363193    0.005173    0.760247    11.00000    0.02750    0.02728 =
         0.01660    0.00183    0.00903    0.00136
AFIX  43
H5    3    0.359897   -0.115174    0.820222    11.00000   -1.20000
AFIX   0
C6    2    0.412794   -0.044085    0.668760    11.00000    0.02422    0.02634 =
         0.01809   -0.00103    0.01009   -0.00101
AFIX  43
H6    3    0.439581   -0.200213    0.662507    11.00000   -1.20000
AFIX   0
N2    1    0.988428    0.108503    0.979626    11.00000    0.02899    0.02843 =
         0.01670    0.00152    0.01080    0.00089
C7    2    0.922255    0.128755    0.835914    11.00000    0.02558    0.02894 =
         0.01614    0.00157    0.01044    0.00034
C8    2    0.911034   -0.062743    0.745046    11.00000    0.02966    0.02416 =
         0.01989    0.00064    0.01204   -0.00030
AFIX  43
H8    3    0.938731   -0.217477    0.779430    11.00000   -1.20000
AFIX   0
C9    2    0.858448   -0.019867    0.603819    11.00000    0.02789    0.02811 =
         0.01975   -0.00163    0.01063   -0.00212
AFIX  43
H9    3    0.850812   -0.145012    0.541575    11.00000   -1.20000
AFIX   0
C10   2    0.817429    0.209443    0.555883    11.00000    0.02960    0.03099 =
         0.01844    0.00181    0.01102    0.00051
AFIX  43
H10   3    0.781260    0.238681    0.460439    11.00000   -1.20000
AFIX   0
C11   2    0.828850    0.396989    0.646528    11.00000    0.03559    0.02769 =
         0.02069    0.00337    0.01507    0.00317
AFIX  43
H11   3    0.801255    0.551611    0.611827    11.00000   -1.20000
AFIX   0
C12   2    0.880652    0.357845    0.787825    11.00000    0.03185    0.02698 =
         0.01716    0.00147    0.01124    0.00128
AFIX  43
H12   3    0.887367    0.483565    0.849411    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0136_bn1 in P2(1)/c
REM wR2 = 0.2476, GooF = S = 1.138, Restrained GooF = 1.130 for all data
REM R1 = 0.0817 for 2079 Fo > 4sig(Fo) and 0.0925 for all 2608 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.1785      0.0000

REM Highest difference peak  0.388,  deepest hole -0.282,  1-sigma level  0.069
Q1    1   0.8140  0.0739  0.5511  11.00000  0.05    0.39
Q2    1   0.9724  0.0286  0.8093  11.00000  0.05    0.34
Q3    1   0.3632  0.0531  0.6044  11.00000  0.05    0.30
Q4    1   0.9357  0.2595  0.8405  11.00000  0.05    0.29
Q5    1   0.3750  0.3135  0.7462  11.00000  0.05    0.28
Q6    1   0.8623  0.1120  0.5938  11.00000  0.05    0.28
Q7    1   0.8884  0.2266  0.7994  11.00000  0.05    0.28
Q8    1   0.3698 -0.0058  0.7035  11.00000  0.05    0.27
Q9    1   0.4599  0.2733  0.6472  11.00000  0.05    0.26
Q10   1   0.8761  0.3128  0.6210  11.00000  0.05    0.25
Q11   1   1.0500  0.1975  1.0412  11.00000  0.05    0.25
Q12   1   0.8095  0.2784  0.6082  11.00000  0.05    0.25
Q13   1   0.8850  0.0345  0.7807  11.00000  0.05    0.25
Q14   1   0.2713  0.3376  0.7022  11.00000  0.05    0.25
Q15   1   0.3153  0.1010  0.7589  11.00000  0.05    0.25
Q16   1   0.3890  0.2244  0.5816  11.00000  0.05    0.24
Q17   1   1.0000  0.0000  1.0000  10.50000  0.05    0.24
Q18   1   0.9244  0.2816  0.7392  11.00000  0.05    0.24
Q19   1   0.9291 -0.0395  0.8401  11.00000  0.05    0.23
Q20   1   0.9410 -0.0071  0.9453  11.00000  0.05    0.23
;
_shelx_res_checksum              15962
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_0p2GPa
_database_code_depnum_ccdc_archive 'CCDC 2336563'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_0p2GPa          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.337 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT149_AZO_0p2GPa          
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.07 Degree
RESPONSE: Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree.
;
_vrf_PLAT911_AZO_0p2GPa          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        738 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3q (K.Radacki, 2005-22)'
_audit_creation_date             2023-03-15
_shelx_SHELXL_version_number     2018/3

loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   15.088(13)
_cell_length_b                   5.7289(4)
_cell_length_c                   12.059(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.42(7)
_cell_angle_gamma                90
_cell_volume                     963.6(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       193000
_cell_measurement_reflns_used    342
_cell_measurement_theta_min      2.3100
_cell_measurement_theta_max      16.5500

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.11517
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 Crystals were grown from saturated solution. For data collection the crystal 
 was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         193000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    0.20    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.0291672000
_diffrn_orient_matrix_UB_12      0.0061113000
_diffrn_orient_matrix_UB_13      0.0171943000
_diffrn_orient_matrix_UB_21      -0.0034261000
_diffrn_orient_matrix_UB_22      0.0191041000
_diffrn_orient_matrix_UB_23      0.0308744000
_diffrn_orient_matrix_UB_31      0.0016404000
_diffrn_orient_matrix_UB_32      -0.0686884000
_diffrn_orient_matrix_UB_33      0.0101246000
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            4279
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.949
_diffrn_reflns_theta_max         21.261
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.201
_diffrn_measured_fraction_theta_full 0.337
_diffrn_reflns_Laue_measured_fraction_max 0.201
_diffrn_reflns_Laue_measured_fraction_full 0.337
_diffrn_reflns_point_group_measured_fraction_max 0.201
_diffrn_reflns_point_group_measured_fraction_full 0.337
_reflns_number_total             4279
_reflns_number_gt                2992
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
The BASF parameter was refined to 46.2%. The anisotropic displacement 
parameters of the disordered nitrogen atoms N2A and N2B were restrained to 
similar behaviour using SIMU restraint. The anisotropic displacement 
parameters of all atoms were restrained to isotropic behqaviour using ISOR 
restraint.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0834P)²+0.0206P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4279
_refine_ls_number_parameters     138
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_ref         0.1783
_refine_ls_wR_factor_gt          0.1587
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.036
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4890(3) 0.1036(3) 0.5041(2) 0.0419(14) Uani 1 1 d . U . . .
C1 C 0.4319(4) 0.1364(4) 0.5741(3) 0.0369(15) Uani 1 1 d . U . . .
C2 C 0.3847(4) 0.3470(4) 0.5605(3) 0.0437(16) Uani 1 1 d . U . . .
H2 H 0.391081 0.458551 0.507938 0.052 Uiso 1 1 calc R U . . .
C3 C 0.3280(4) 0.3926(4) 0.6247(3) 0.0501(18) Uani 1 1 d . U . . .
H3 H 0.294315 0.532294 0.613212 0.060 Uiso 1 1 calc R U . . .
C4 C 0.3213(4) 0.2300(5) 0.7063(4) 0.0511(19) Uani 1 1 d . U . . .
H4 H 0.283734 0.261120 0.750288 0.061 Uiso 1 1 calc R U . . .
C5 C 0.3705(4) 0.0224(5) 0.7220(3) 0.0474(18) Uani 1 1 d . U . . .
H5 H 0.366012 -0.085726 0.777100 0.057 Uiso 1 1 calc R U . . .
C6 C 0.4266(4) -0.0282(4) 0.6571(3) 0.0391(15) Uani 1 1 d . U . . .
H6 H 0.459912 -0.168405 0.668374 0.047 Uiso 1 1 calc R U . . .
N2A N 0.9695(8) 0.0759(6) 0.9770(9) 0.050(3) Uani 0.86(2) 1 d . U P A 1
N2B N 0.992(4) -0.081(4) 0.961(5) 0.051(4) Uani 0.14(2) 1 d . U P A 2
C7 C 0.9203(5) 0.0495(5) 0.8499(4) 0.052(2) Uani 1 1 d . U . . .
C8 C 0.9282(5) -0.1368(5) 0.7803(4) 0.057(2) Uani 1 1 d . U . . .
H8 H 0.968305 -0.262134 0.815398 0.068 Uiso 1 1 calc R U . . .
C9 C 0.8756(6) -0.1327(6) 0.6578(4) 0.063(2) Uani 1 1 d . U . . .
H9 H 0.880258 -0.256476 0.610493 0.076 Uiso 1 1 calc R U . . .
C10 C 0.8161(5) 0.0532(6) 0.6052(4) 0.062(3) Uani 1 1 d . U . . .
H10 H 0.780790 0.055107 0.522955 0.075 Uiso 1 1 calc R U . . .
C11 C 0.8098(5) 0.2354(6) 0.6761(4) 0.063(2) Uani 1 1 d . U . . .
H11 H 0.770584 0.362162 0.641141 0.075 Uiso 1 1 calc R U . . .
C12 C 0.8600(5) 0.2328(5) 0.7964(4) 0.060(2) Uani 1 1 d . U . . .
H12 H 0.853744 0.355843 0.843184 0.072 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.045(4) 0.0424(10) 0.0430(18) 0.0007(8) 0.022(3) 0.0029(11)
C1 0.034(5) 0.0404(11) 0.0364(19) -0.0040(9) 0.013(3) -0.0011(13)
C2 0.043(5) 0.0434(13) 0.044(2) 0.0013(10) 0.016(3) 0.0042(14)
C3 0.044(6) 0.0488(14) 0.059(3) -0.0051(12) 0.021(4) 0.0076(16)
C4 0.047(6) 0.0605(16) 0.053(3) -0.0094(13) 0.027(4) -0.0014(17)
C5 0.047(6) 0.0560(15) 0.043(2) 0.0000(11) 0.022(4) -0.0049(16)
C6 0.034(5) 0.0427(12) 0.040(2) 0.0016(9) 0.014(3) 0.0026(13)
N2A 0.046(7) 0.0569(17) 0.045(5) 0.0036(15) 0.013(5) 0.0076(19)
N2B 0.046(9) 0.057(6) 0.045(7) 0.001(6) 0.012(9) 0.007(6)
C7 0.042(7) 0.0684(18) 0.046(3) 0.0063(14) 0.017(4) -0.005(2)
C8 0.042(7) 0.0616(18) 0.064(3) 0.0070(14) 0.018(4) 0.0039(18)
C9 0.058(8) 0.0693(19) 0.065(3) -0.0130(16) 0.027(5) -0.005(2)
C10 0.049(8) 0.089(2) 0.046(3) 0.0028(17) 0.015(5) -0.006(3)
C11 0.051(8) 0.073(2) 0.065(3) 0.0166(16) 0.023(5) 0.015(2)
C12 0.062(7) 0.0651(18) 0.057(3) 0.0008(14) 0.027(4) 0.003(2)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.247(4) 3_656 ?
N1 C1 1.429(4) . ?
C1 C2 1.379(5) . ?
C1 C6 1.399(3) . ?
C2 C3 1.380(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2A N2A 1.233(16) 3_757 ?
N2A C7 1.434(11) . ?
N2B N2B 1.27(7) 3_757 ?
N2B C7 1.56(6) . ?
C7 C12 1.378(7) . ?
C7 C8 1.391(4) . ?
C8 C9 1.385(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.381(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.356(8) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 114.2(3) 3_656 . ?
C2 C1 C6 120.4(3) . . ?
C2 C1 N1 116.4(2) . . ?
C6 C1 N1 123.1(3) . . ?
C1 C2 C3 120.1(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 121.1(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 118.5(3) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
N2A N2A C7 113.6(7) 3_757 . ?
N2B N2B C7 99(4) 3_757 . ?
C12 C7 C8 119.7(5) . . ?
C12 C7 N2A 113.6(3) . . ?
C8 C7 N2A 126.7(5) . . ?
C12 C7 N2B 152.5(11) . . ?
C8 C7 N2B 87.7(12) . . ?
C9 C8 C7 118.9(4) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 119.1(5) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C12 C11 C10 120.9(5) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C7 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -163.3(5) 3_656 . . . ?
N1 N1 C1 C6 19.7(7) 3_656 . . . ?
C6 C1 C2 C3 -3.1(7) . . . . ?
N1 C1 C2 C3 179.9(4) . . . . ?
C1 C2 C3 C4 2.4(8) . . . . ?
C2 C3 C4 C5 -0.7(8) . . . . ?
C3 C4 C5 C6 -0.3(7) . . . . ?
C4 C5 C6 C1 -0.4(7) . . . . ?
C2 C1 C6 C5 2.0(7) . . . . ?
N1 C1 C6 C5 178.8(4) . . . . ?
N2A N2A C7 C12 -173.1(7) 3_757 . . . ?
N2A N2A C7 C8 6.9(11) 3_757 . . . ?
N2B N2B C7 C12 -11(7) 3_757 . . . ?
N2B N2B C7 C8 171(4) 3_757 . . . ?
C12 C7 C8 C9 0.5(7) . . . . ?
N2A C7 C8 C9 -179.6(5) . . . . ?
N2B C7 C8 C9 179.4(17) . . . . ?
C7 C8 C9 C10 0.1(8) . . . . ?
C8 C9 C10 C11 0.1(8) . . . . ?
C9 C10 C11 C12 -0.9(8) . . . . ?
C10 C11 C12 C7 1.5(9) . . . . ?
C8 C7 C12 C11 -1.3(8) . . . . ?
N2A C7 C12 C11 178.7(5) . . . . ?
N2B C7 C12 C11 -179(4) . . . . ?


_shelx_res_file                  
;
TITL sample_0009_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 19:28:03 on 23-Feb-2023
REM P2(1)/c (#14 in standard setting)
CELL 0.41000  15.087746   5.728928  12.059176  90.0000 112.4178  90.0000
ZERR    4.00   0.012914   0.000423   0.003843   0.0000   0.0687   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
OMIT 5 -6 1
OMIT -3 -1 1
OMIT 3 1 -1
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.03
FMAP 2
PLAN 20
WGHT    0.083400    0.020600
BASF   0.46202
FVAR      22.24625   0.86184
N1    1    0.488982    0.103641    0.504085    11.00000    0.04521    0.04238 =
         0.04297    0.00065    0.02218    0.00286
C1    2    0.431938    0.136360    0.574092    11.00000    0.03380    0.04045 =
         0.03637   -0.00395    0.01328   -0.00109
C2    2    0.384714    0.347044    0.560462    11.00000    0.04295    0.04337 =
         0.04440    0.00132    0.01623    0.00424
AFIX  43
H2    3    0.391081    0.458551    0.507938    11.00000   -1.20000
AFIX   0
C3    2    0.328026    0.392572    0.624678    11.00000    0.04432    0.04875 =
         0.05858   -0.00506    0.02101    0.00763
AFIX  43
H3    3    0.294315    0.532294    0.613212    11.00000   -1.20000
AFIX   0
C4    2    0.321337    0.229989    0.706284    11.00000    0.04688    0.06049 =
         0.05335   -0.00941    0.02741   -0.00145
AFIX  43
H4    3    0.283734    0.261120    0.750288    11.00000   -1.20000
AFIX   0
C5    2    0.370509    0.022421    0.721968    11.00000    0.04733    0.05602 =
         0.04286    0.00002    0.02174   -0.00487
AFIX  43
H5    3    0.366012   -0.085726    0.777100    11.00000   -1.20000
AFIX   0
C6    2    0.426563   -0.028169    0.657072    11.00000    0.03407    0.04265 =
         0.04002    0.00158    0.01351    0.00256
AFIX  43
H6    3    0.459912   -0.168405    0.668374    11.00000   -1.20000
AFIX   0
REM SIMU 0.003 C7 > C12
SIMU 0.003 N2A N2B
PART 1 21.
N2A   1    0.969534    0.075864    0.976997    21.00000    0.04560    0.05692 =
         0.04518    0.00363    0.01321    0.00759
PART 2 -21.
N2B   1    0.992217   -0.080628    0.961068   -21.00000    0.04564    0.05723 =
         0.04533    0.00054    0.01212    0.00689
PART 0
C7    2    0.920307    0.049506    0.849884    11.00000    0.04150    0.06844 =
         0.04608    0.00629    0.01673   -0.00520
C8    2    0.928249   -0.136811    0.780270    11.00000    0.04237    0.06163 =
         0.06403    0.00702    0.01827    0.00392
AFIX  43
H8    3    0.968305   -0.262134    0.815398    11.00000   -1.20000
AFIX   0
C9    2    0.875554   -0.132670    0.657831    11.00000    0.05808    0.06929 =
         0.06499   -0.01297    0.02725   -0.00492
AFIX  43
H9    3    0.880258   -0.256476    0.610493    11.00000   -1.20000
AFIX   0
C10   2    0.816099    0.053175    0.605215    11.00000    0.04890    0.08944 =
         0.04615    0.00283    0.01482   -0.00564
AFIX  43
H10   3    0.780790    0.055107    0.522955    11.00000   -1.20000
AFIX   0
C11   2    0.809808    0.235438    0.676136    11.00000    0.05117    0.07318 =
         0.06528    0.01662    0.02345    0.01533
AFIX  43
H11   3    0.770584    0.362162    0.641141    11.00000   -1.20000
AFIX   0
C12   2    0.860039    0.232816    0.796403    11.00000    0.06243    0.06510 =
         0.05687    0.00077    0.02733    0.00325
AFIX  43
H12   3    0.853744    0.355843    0.843184    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0009_bn1 in P2(1)/c
REM wR2 = 0.1783, GooF = S = 1.051, Restrained GooF = 1.039 for all data
REM R1 = 0.0620 for 2992 Fo > 4sig(Fo) and 0.0862 for all 4279 data
REM 138 parameters refined using 96 restraints

END

WGHT      0.0834      0.0206

REM Highest difference peak  0.201,  deepest hole -0.185,  1-sigma level  0.036
Q1    1   0.4287  0.0610  0.6116  11.00000  0.05    0.20
Q2    1   0.3496  0.3184  0.6893  11.00000  0.05    0.17
Q3    1   0.8971 -0.3351  0.9147  11.00000  0.05    0.14
Q4    1   0.3836 -0.0356  0.6759  11.00000  0.05    0.13
Q5    1   0.4589  0.1018  0.5476  11.00000  0.05    0.13
Q6    1   0.3623  0.3448  0.6081  11.00000  0.05    0.13
Q7    1   0.9406 -0.3962  0.9587  11.00000  0.05    0.12
Q8    1   0.4787  0.1943  0.4511  11.00000  0.05    0.12
Q9    1   0.8884 -0.1840  0.7019  11.00000  0.05    0.11
Q10   1   0.2087  0.1747  0.8012  11.00000  0.05    0.11
Q11   1   0.4080 -0.0847  0.8380  11.00000  0.05    0.11
Q12   1   0.4330  0.0496  0.7164  11.00000  0.05    0.11
Q13   1   0.7813  0.3380  0.7956  11.00000  0.05    0.10
Q14   1   0.5892  0.2666  0.5337  11.00000  0.05    0.10
Q15   1   0.9247 -0.0576  0.8259  11.00000  0.05    0.10
Q16   1   0.9703 -0.2061  1.0022  11.00000  0.05    0.10
Q17   1   0.4109  0.6821  0.5082  11.00000  0.05    0.10
Q18   1   0.1944  0.2808  0.7376  11.00000  0.05    0.10
Q19   1   0.9197 -0.2923  0.9696  11.00000  0.05    0.10
Q20   1   0.8527 -0.1636  0.8373  11.00000  0.05    0.10
;
_shelx_res_checksum              14130
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_11GPa
_database_code_depnum_ccdc_archive 'CCDC 2336569'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_11GPa           
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.349 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT411_AZO_11GPa           
;
PROBLEM: Short Inter H...H Contact  H2       ..H11      .       1.94 Ang.  
RESPONSE: Intermolecular distances are strongly shortened at high 
pressure and atoms approach closer to one another than at ambient 
conditions or low temperature.
;
_vrf_PLAT911_AZO_11GPa           
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        554 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3r (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-16
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   13.220(8)
_cell_length_b                   5.1750(2)
_cell_length_c                   10.904(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.08(5)
_cell_angle_gamma                90
_cell_volume                     686.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       11020000
_cell_measurement_reflns_used    476
_cell_measurement_theta_min      2.1500
_cell_measurement_theta_max      21.6450

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75733
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         11020000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    0.50    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0335647192
_diffrn_orient_matrix_UB_12      0.0070810588
_diffrn_orient_matrix_UB_13      -0.0184742312
_diffrn_orient_matrix_UB_21      0.0029987375
_diffrn_orient_matrix_UB_22      0.0217843837
_diffrn_orient_matrix_UB_23      -0.0345474684
_diffrn_orient_matrix_UB_31      -0.0022072811
_diffrn_orient_matrix_UB_32      -0.0757586190
_diffrn_orient_matrix_UB_33      -0.0116010131
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            3125
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.342
_diffrn_reflns_theta_max         21.659
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.198
_diffrn_measured_fraction_theta_full 0.349
_diffrn_reflns_Laue_measured_fraction_max 0.198
_diffrn_reflns_Laue_measured_fraction_full 0.349
_diffrn_reflns_point_group_measured_fraction_max 0.198
_diffrn_reflns_point_group_measured_fraction_full 0.349
_reflns_number_total             3125
_reflns_number_gt                2534
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
The BASF parameter was refined to 32.6%. The atomic displacement parameters 
of atoms N2A, N2B and C7 were restraint with RIGU keyword in ShelXL input 
('enhanced rigid bond' restraint for all bonds in the connectivity list).
The anisotropic displacement parameters 
of the disordered nitrogen atoms N2A and N2B were restrained to 
similar behaviour using SIMU restraint.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1295P)²+0.1540P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3125
_refine_ls_number_parameters     138
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0706
_refine_ls_wR_factor_ref         0.2064
_refine_ls_wR_factor_gt          0.1966
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.071
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4897(5) 0.1161(4) 0.5068(3) 0.0217(16) Uani 1 1 d . . . . .
C1 C 0.4279(5) 0.1475(5) 0.5849(4) 0.0220(19) Uani 1 1 d . . . . .
C2 C 0.3775(5) 0.3828(5) 0.5777(4) 0.0219(19) Uani 1 1 d . . . . .
H2 H 0.382736 0.510055 0.520195 0.026 Uiso 1 1 calc R U . . .
C3 C 0.3194(6) 0.4287(5) 0.6562(4) 0.0225(19) Uani 1 1 d . . . . .
H3 H 0.281077 0.582943 0.647202 0.027 Uiso 1 1 calc R U . . .
C4 C 0.3177(6) 0.2468(5) 0.7483(4) 0.0233(19) Uani 1 1 d . . . . .
H4 H 0.280252 0.280701 0.803193 0.028 Uiso 1 1 calc R U . . .
C5 C 0.3720(5) 0.0138(5) 0.7583(4) 0.0219(19) Uani 1 1 d . . . . .
H5 H 0.373248 -0.106645 0.822216 0.026 Uiso 1 1 calc R U . . .
C6 C 0.4240(5) -0.0398(5) 0.6741(4) 0.0209(18) Uani 1 1 d . . . . .
H6 H 0.456407 -0.200361 0.676847 0.025 Uiso 1 1 calc R U . . .
N2A N 0.9637(12) 0.0797(7) 0.9744(11) 0.029(3) Uani 0.74(2) 1 d . U P A 1
N2B N 0.986(3) -0.097(2) 0.957(3) 0.030(4) Uani 0.26(2) 1 d . U P A 2
C7 C 0.9145(7) 0.0417(8) 0.8327(5) 0.033(3) Uani 1 1 d . . . . .
C8 C 0.9236(8) -0.1642(7) 0.7591(6) 0.039(3) Uani 1 1 d . . . . .
H8 H 0.962814 -0.310529 0.800995 0.047 Uiso 1 1 calc R U . . .
C9 C 0.8743(7) -0.1521(7) 0.6227(6) 0.039(3) Uani 1 1 d . . . . .
H9 H 0.880428 -0.289966 0.571339 0.047 Uiso 1 1 calc R U . . .
C10 C 0.8160(8) 0.0636(8) 0.5623(5) 0.034(3) Uani 1 1 d . . . . .
H10 H 0.782192 0.072063 0.469871 0.041 Uiso 1 1 calc R U . . .
C11 C 0.8075(7) 0.2677(7) 0.6384(6) 0.038(3) Uani 1 1 d . . . . .
H11 H 0.768240 0.414513 0.597460 0.045 Uiso 1 1 calc R U . . .
C12 C 0.8562(7) 0.2549(6) 0.7727(5) 0.034(2) Uani 1 1 d . . . . .
H12 H 0.849829 0.392318 0.824190 0.041 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.027(5) 0.0215(11) 0.0200(19) -0.0015(8) 0.013(3) -0.0003(13)
C1 0.030(6) 0.0201(12) 0.020(2) -0.0013(9) 0.015(4) -0.0005(15)
C2 0.027(6) 0.0200(12) 0.021(2) 0.0008(9) 0.012(4) 0.0007(14)
C3 0.024(6) 0.0217(12) 0.024(2) -0.0013(10) 0.012(4) 0.0023(15)
C4 0.026(6) 0.0258(14) 0.023(2) -0.0020(10) 0.014(4) 0.0000(15)
C5 0.025(6) 0.0231(13) 0.020(2) 0.0011(10) 0.011(4) -0.0004(15)
C6 0.025(6) 0.0188(11) 0.021(2) -0.0005(9) 0.012(3) -0.0002(14)
N2A 0.037(10) 0.0314(19) 0.022(5) 0.0016(17) 0.016(7) 0.006(2)
N2B 0.035(13) 0.037(5) 0.022(7) 0.001(4) 0.017(9) -0.002(6)
C7 0.024(9) 0.053(2) 0.020(3) 0.0060(15) 0.006(5) -0.010(2)
C8 0.033(8) 0.0307(18) 0.056(4) 0.0094(16) 0.021(5) 0.003(2)
C9 0.030(9) 0.042(2) 0.053(4) -0.0194(17) 0.026(6) -0.009(2)
C10 0.019(9) 0.063(2) 0.020(3) 0.0014(16) 0.006(5) -0.009(3)
C11 0.033(8) 0.0372(18) 0.049(4) 0.0151(16) 0.023(5) 0.007(2)
C12 0.038(8) 0.0359(17) 0.040(3) -0.0075(14) 0.027(5) -0.008(2)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.254(5) 3_656 ?
N1 C1 1.402(4) . ?
C1 C2 1.375(5) . ?
C1 C6 1.388(3) . ?
C2 C3 1.377(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2A N2A 1.22(2) 3_757 ?
N2A C7 1.436(12) . ?
N2B N2B 1.32(5) 3_757 ?
N2B C7 1.50(3) . ?
C7 C12 1.357(8) . ?
C7 C8 1.368(6) . ?
C8 C9 1.371(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.370(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.351(8) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 112.9(3) 3_656 . ?
C2 C1 C6 120.6(3) . . ?
C2 C1 N1 116.9(2) . . ?
C6 C1 N1 122.3(3) . . ?
C1 C2 C3 119.5(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2A N2A C7 110.0(7) 3_757 . ?
N2B N2B C7 100(2) 3_757 . ?
C12 C7 C8 121.0(5) . . ?
C12 C7 N2A 109.8(4) . . ?
C8 C7 N2A 129.1(6) . . ?
C12 C7 N2B 149.6(8) . . ?
C8 C7 N2B 89.4(8) . . ?
C7 C8 C9 119.1(5) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.0(5) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.0(5) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 120.1(3) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -163.8(6) 3_656 . . . ?
N1 N1 C1 C6 21.4(9) 3_656 . . . ?
C6 C1 C2 C3 -2.5(9) . . . . ?
N1 C1 C2 C3 -177.4(5) . . . . ?
C1 C2 C3 C4 4.4(9) . . . . ?
C2 C3 C4 C5 -2.1(9) . . . . ?
C3 C4 C5 C6 -2.3(9) . . . . ?
C4 C5 C6 C1 4.2(9) . . . . ?
C2 C1 C6 C5 -1.8(9) . . . . ?
N1 C1 C6 C5 172.8(5) . . . . ?
N2A N2A C7 C12 -163.6(10) 3_757 . . . ?
N2A N2A C7 C8 13.5(16) 3_757 . . . ?
N2B N2B C7 C12 -14(4) 3_757 . . . ?
N2B N2B C7 C8 163(3) 3_757 . . . ?
C12 C7 C8 C9 0.9(11) . . . . ?
N2A C7 C8 C9 -176.0(8) . . . . ?
N2B C7 C8 C9 -177.7(12) . . . . ?
C7 C8 C9 C10 -0.6(11) . . . . ?
C8 C9 C10 C11 0.3(10) . . . . ?
C9 C10 C11 C12 -0.3(11) . . . . ?
C10 C11 C12 C7 0.6(11) . . . . ?
C8 C7 C12 C11 -1.0(10) . . . . ?
N2A C7 C12 C11 176.5(7) . . . . ?
N2B C7 C12 C11 176(2) . . . . ?


_shelx_res_file                  
;
TITL sample_0101_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 22:54:02 on 24-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  13.219968   5.174997  10.903993  90.0000 113.0757  90.0000
ZERR    4.00   0.008468   0.000223   0.002568   0.0000   0.0514   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
SIMU 0.005 0.01 2 N2A N2B
rigU 0.005 0.01 N2A N2B C7
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
REM ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.129500    0.154000
BASF   0.32587
FVAR      25.27032   0.74218
N1    1    0.489689    0.116105    0.506779    11.00000    0.02701    0.02154 =
         0.02003   -0.00155    0.01306   -0.00031
C1    2    0.427852    0.147537    0.584877    11.00000    0.03002    0.02007 =
         0.02035   -0.00134    0.01480   -0.00050
C2    2    0.377540    0.382815    0.577677    11.00000    0.02745    0.02001 =
         0.02071    0.00080    0.01196    0.00071
AFIX  43
H2    3    0.382736    0.510055    0.520195    11.00000   -1.20000
AFIX   0
C3    2    0.319416    0.428680    0.656172    11.00000    0.02388    0.02166 =
         0.02403   -0.00134    0.01152    0.00226
AFIX  43
H3    3    0.281077    0.582943    0.647202    11.00000   -1.20000
AFIX   0
C4    2    0.317651    0.246802    0.748332    11.00000    0.02557    0.02580 =
         0.02260   -0.00203    0.01394    0.00005
AFIX  43
H4    3    0.280252    0.280701    0.803193    11.00000   -1.20000
AFIX   0
C5    2    0.371986    0.013795    0.758331    11.00000    0.02481    0.02307 =
         0.01956    0.00106    0.01066   -0.00043
AFIX  43
H5    3    0.373248   -0.106645    0.822216    11.00000   -1.20000
AFIX   0
C6    2    0.424008   -0.039777    0.674101    11.00000    0.02501    0.01882 =
         0.02115   -0.00050    0.01155   -0.00022
AFIX  43
H6    3    0.456407   -0.200361    0.676847    11.00000   -1.20000
AFIX   0
PART 1 21.
N2A   1    0.963670    0.079730    0.974429    21.00000    0.03657    0.03136 =
         0.02237    0.00160    0.01606    0.00556
PART 2 -21.
N2B   1    0.985954   -0.096853    0.957444   -21.00000    0.03531    0.03713 =
         0.02157    0.00095    0.01658   -0.00180
PART 0
C7    2    0.914468    0.041747    0.832677    11.00000    0.02372    0.05283 =
         0.01996    0.00599    0.00594   -0.01017
C8    2    0.923641   -0.164200    0.759091    11.00000    0.03338    0.03074 =
         0.05621    0.00940    0.02147    0.00281
AFIX  43
H8    3    0.962814   -0.310529    0.800995    11.00000   -1.20000
AFIX   0
C9    2    0.874312   -0.152075    0.622701    11.00000    0.02986    0.04230 =
         0.05343   -0.01943    0.02552   -0.00914
AFIX  43
H9    3    0.880428   -0.289966    0.571339    11.00000   -1.20000
AFIX   0
C10   2    0.816017    0.063638    0.562331    11.00000    0.01869    0.06265 =
         0.01955    0.00141    0.00641   -0.00897
AFIX  43
H10   3    0.782192    0.072063    0.469871    11.00000   -1.20000
AFIX   0
C11   2    0.807521    0.267668    0.638438    11.00000    0.03350    0.03718 =
         0.04857    0.01511    0.02262    0.00708
AFIX  43
H11   3    0.768240    0.414513    0.597460    11.00000   -1.20000
AFIX   0
C12   2    0.856216    0.254898    0.772727    11.00000    0.03823    0.03588 =
         0.03961   -0.00748    0.02711   -0.00789
AFIX  43
H12   3    0.849829    0.392318    0.824190    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0101_bn1 in P2(1)/c
REM wR2 = 0.2064, GooF = S = 1.070, Restrained GooF = 1.069 for all data
REM R1 = 0.0706 for 2534 Fo > 4sig(Fo) and 0.0816 for all 3125 data
REM 138 parameters refined using 12 restraints

END

WGHT      0.1295      0.1540

REM Highest difference peak  0.495,  deepest hole -0.396,  1-sigma level  0.071
Q1    1   0.9326 -0.0359  0.8066  11.00000  0.05    0.50
Q2    1   0.9122 -0.2212  0.7099  11.00000  0.05    0.35
Q3    1   0.3907  0.2475  0.5804  11.00000  0.05    0.34
Q4    1   0.3384  0.1331  0.7495  11.00000  0.05    0.32
Q5    1   0.3009  0.3235  0.6807  11.00000  0.05    0.32
Q6    1   0.5000  0.0000  0.5000  10.50000  0.05    0.31
Q7    1   0.8239  0.1572  0.5988  11.00000  0.05    0.30
Q8    1   0.9156  0.1438  0.8132  11.00000  0.05    0.29
Q9    1   0.4280  0.0665  0.6326  11.00000  0.05    0.29
Q10   1   0.8266  0.2267  0.7095  11.00000  0.05    0.29
Q11   1   0.3811  0.0082  0.7000  11.00000  0.05    0.27
Q12   1   0.3513  0.4310  0.6087  11.00000  0.05    0.23
Q13   1   0.8683 -0.1443  0.6823  11.00000  0.05    0.22
Q14   1   0.4575  0.0738  0.5510  11.00000  0.05    0.22
Q15   1   0.4967  0.1555  0.5709  11.00000  0.05    0.21
Q16   1   0.9342  0.1590  0.9858  11.00000  0.05    0.21
Q17   1   0.8495 -0.0923  0.5692  11.00000  0.05    0.18
Q18   1   0.9130 -0.0510  0.9766  11.00000  0.05    0.17
Q19   1   0.4240  0.4577  0.7594  11.00000  0.05    0.17
Q20   1   0.4824  0.1893  0.4586  11.00000  0.05    0.17
;
_shelx_res_checksum              64640
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_10p6GPa
_database_code_depnum_ccdc_archive 'CCDC 2336568'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_10p6GPa         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.346 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT411_AZO_10p6GPa         
;
PROBLEM: Short Inter H...H Contact  H2       ..H11      .       1.94 Ang.  
RESPONSE: Intermolecular distances are strongly shortened at high 
pressure and atoms approach closer to one another than at ambient 
conditions or low temperature.
;
_vrf_PLAT911_AZO_10p6GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        555 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3r (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-16
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   13.261(8)
_cell_length_b                   5.1782(2)
_cell_length_c                   10.915(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.01(5)
_cell_angle_gamma                90
_cell_volume                     689.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       10580000
_cell_measurement_reflns_used    524
_cell_measurement_theta_min      2.3350
_cell_measurement_theta_max      21.5810

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.754
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.66805
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         10580000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    0.50    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0334433676
_diffrn_orient_matrix_UB_12      0.0070489556
_diffrn_orient_matrix_UB_13      -0.0184388535
_diffrn_orient_matrix_UB_21      0.0030177706
_diffrn_orient_matrix_UB_22      0.0217212731
_diffrn_orient_matrix_UB_23      -0.0344956678
_diffrn_orient_matrix_UB_31      -0.0021950154
_diffrn_orient_matrix_UB_32      -0.0757417483
_diffrn_orient_matrix_UB_33      -0.0115780816
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            3215
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.153
_diffrn_reflns_theta_max         21.642
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.197
_diffrn_measured_fraction_theta_full 0.346
_diffrn_reflns_Laue_measured_fraction_max 0.197
_diffrn_reflns_Laue_measured_fraction_full 0.346
_diffrn_reflns_point_group_measured_fraction_max 0.197
_diffrn_reflns_point_group_measured_fraction_full 0.346
_reflns_number_total             3215
_reflns_number_gt                2740
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
The BASF parameter was refined to 36.2%. The anisotropic displacement parameters 
of the disordered nitrogen atoms N2A and N2B were restrained to 
similar behaviour using SIMU restraint.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1130P)²+0.2310P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3215
_refine_ls_number_parameters     138
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.1941
_refine_ls_wR_factor_gt          0.1874
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.064
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4897(4) 0.1160(4) 0.5068(3) 0.0210(15) Uani 1 1 d . . . . .
C1 C 0.4280(5) 0.1474(5) 0.5848(3) 0.0204(18) Uani 1 1 d . . . . .
C2 C 0.3775(5) 0.3824(5) 0.5773(4) 0.0211(18) Uani 1 1 d . . . . .
H2 H 0.382505 0.509450 0.519709 0.025 Uiso 1 1 calc R U . . .
C3 C 0.3194(5) 0.4281(5) 0.6556(4) 0.0217(18) Uani 1 1 d . . . . .
H3 H 0.281056 0.582062 0.646483 0.026 Uiso 1 1 calc R U . . .
C4 C 0.3177(5) 0.2465(5) 0.7477(4) 0.0222(18) Uani 1 1 d . . . . .
H4 H 0.280254 0.280364 0.802406 0.027 Uiso 1 1 calc R U . . .
C5 C 0.3721(5) 0.0139(5) 0.7580(4) 0.0206(18) Uani 1 1 d . . . . .
H5 H 0.373319 -0.106322 0.821841 0.025 Uiso 1 1 calc R U . . .
C6 C 0.4241(5) -0.0396(5) 0.6740(4) 0.0196(16) Uani 1 1 d . . . . .
H6 H 0.456538 -0.200035 0.676890 0.023 Uiso 1 1 calc R U . . .
N2A N 0.9638(10) 0.0790(7) 0.9746(9) 0.030(3) Uani 0.772(19) 1 d . U P A 1
N2B N 0.987(3) -0.097(2) 0.958(3) 0.030(3) Uani 0.228(19) 1 d . U P A 2
C7 C 0.9147(7) 0.0429(7) 0.8333(5) 0.031(2) Uani 1 1 d . . . . .
C8 C 0.9243(7) -0.1642(6) 0.7604(5) 0.037(2) Uani 1 1 d . . . . .
H8 H 0.963785 -0.309597 0.802680 0.044 Uiso 1 1 calc R U . . .
C9 C 0.8747(7) -0.1540(7) 0.6239(6) 0.039(3) Uani 1 1 d . . . . .
H9 H 0.881040 -0.292404 0.573164 0.046 Uiso 1 1 calc R U . . .
C10 C 0.8156(7) 0.0607(8) 0.5624(5) 0.034(3) Uani 1 1 d . . . . .
H10 H 0.781547 0.067365 0.470081 0.041 Uiso 1 1 calc R U . . .
C11 C 0.8071(7) 0.2655(6) 0.6380(5) 0.036(2) Uani 1 1 d . . . . .
H11 H 0.767646 0.411547 0.596624 0.044 Uiso 1 1 calc R U . . .
C12 C 0.8560(6) 0.2549(6) 0.7725(5) 0.033(2) Uani 1 1 d . . . . .
H12 H 0.849337 0.392990 0.823340 0.039 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.027(5) 0.0200(11) 0.0209(18) -0.0012(8) 0.014(3) 0.0003(12)
C1 0.027(6) 0.0190(12) 0.020(2) -0.0014(9) 0.014(3) -0.0002(14)
C2 0.026(6) 0.0189(12) 0.021(2) 0.0012(9) 0.012(3) 0.0011(14)
C3 0.023(6) 0.0202(12) 0.025(2) -0.0011(10) 0.012(3) 0.0022(14)
C4 0.024(6) 0.0245(13) 0.023(2) -0.0019(10) 0.013(3) 0.0001(15)
C5 0.022(6) 0.0219(12) 0.019(2) 0.0013(9) 0.010(3) -0.0009(14)
C6 0.022(5) 0.0176(11) 0.022(2) -0.0008(9) 0.012(3) -0.0005(13)
N2A 0.042(9) 0.0299(17) 0.025(5) 0.0009(16) 0.021(6) 0.004(2)
N2B 0.042(11) 0.033(4) 0.024(6) 0.000(4) 0.022(8) 0.001(5)
C7 0.021(8) 0.049(2) 0.020(3) 0.0057(14) 0.006(5) -0.009(2)
C8 0.033(8) 0.0291(17) 0.054(4) 0.0078(15) 0.022(5) 0.0019(19)
C9 0.033(8) 0.0396(19) 0.054(4) -0.0182(17) 0.028(5) -0.009(2)
C10 0.023(9) 0.060(2) 0.021(3) 0.0012(16) 0.009(5) -0.009(3)
C11 0.032(8) 0.0353(17) 0.047(3) 0.0145(15) 0.022(5) 0.007(2)
C12 0.036(7) 0.0336(16) 0.040(3) -0.0071(13) 0.027(4) -0.0077(19)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.254(4) 3_656 ?
N1 C1 1.402(4) . ?
C1 C2 1.376(5) . ?
C1 C6 1.388(3) . ?
C2 C3 1.376(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2A N2A 1.218(19) 3_757 ?
N2A C7 1.432(10) . ?
N2B N2B 1.31(5) 3_757 ?
N2B C7 1.51(3) . ?
C7 C12 1.360(8) . ?
C7 C8 1.371(5) . ?
C8 C9 1.374(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.374(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.355(8) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 112.8(3) 3_656 . ?
C2 C1 C6 120.5(3) . . ?
C2 C1 N1 116.9(2) . . ?
C6 C1 N1 122.4(3) . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2A N2A C7 110.4(6) 3_757 . ?
N2B N2B C7 99(2) 3_757 . ?
C12 C7 C8 120.9(5) . . ?
C12 C7 N2A 110.7(4) . . ?
C8 C7 N2A 128.4(6) . . ?
C12 C7 N2B 150.4(8) . . ?
C8 C7 N2B 88.6(8) . . ?
C7 C8 C9 119.0(5) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 119.7(5) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 120.2(5) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C7 120.1(3) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -163.6(6) 3_656 . . . ?
N1 N1 C1 C6 21.5(9) 3_656 . . . ?
C6 C1 C2 C3 -2.3(8) . . . . ?
N1 C1 C2 C3 -177.4(5) . . . . ?
C1 C2 C3 C4 4.3(9) . . . . ?
C2 C3 C4 C5 -2.0(9) . . . . ?
C3 C4 C5 C6 -2.3(8) . . . . ?
C4 C5 C6 C1 4.2(9) . . . . ?
C2 C1 C6 C5 -1.9(9) . . . . ?
N1 C1 C6 C5 172.9(5) . . . . ?
N2A N2A C7 C12 -163.6(9) 3_757 . . . ?
N2A N2A C7 C8 14.0(14) 3_757 . . . ?
N2B N2B C7 C12 -12(5) 3_757 . . . ?
N2B N2B C7 C8 165(3) 3_757 . . . ?
C12 C7 C8 C9 0.9(10) . . . . ?
N2A C7 C8 C9 -176.5(7) . . . . ?
N2B C7 C8 C9 -177.6(12) . . . . ?
C7 C8 C9 C10 -0.6(10) . . . . ?
C8 C9 C10 C11 0.4(10) . . . . ?
C9 C10 C11 C12 -0.5(10) . . . . ?
C10 C11 C12 C7 0.7(10) . . . . ?
C8 C7 C12 C11 -0.9(10) . . . . ?
N2A C7 C12 C11 176.9(7) . . . . ?
N2B C7 C12 C11 176(2) . . . . ?


_shelx_res_file                  
;
TITL sample_0097_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 22:50:55 on 24-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  13.260762   5.178243  10.914836  90.0000 113.0103  90.0000
ZERR    4.00   0.007845   0.000213   0.002349   0.0000   0.0472   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
REM ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.113000    0.231000
BASF   0.36228
FVAR      25.57629   0.77187
N1    1    0.489714    0.116033    0.506792    11.00000    0.02654    0.01996 =
         0.02086   -0.00122    0.01406    0.00035
C1    2    0.428009    0.147361    0.584785    11.00000    0.02682    0.01899 =
         0.02005   -0.00136    0.01409   -0.00020
C2    2    0.377457    0.382420    0.577279    11.00000    0.02618    0.01886 =
         0.02110    0.00122    0.01231    0.00108
AFIX  43
H2    3    0.382505    0.509450    0.519709    11.00000   -1.20000
AFIX   0
C3    2    0.319403    0.428064    0.655570    11.00000    0.02267    0.02019 =
         0.02499   -0.00107    0.01228    0.00217
AFIX  43
H3    3    0.281056    0.582062    0.646483    11.00000   -1.20000
AFIX   0
C4    2    0.317668    0.246528    0.747706    11.00000    0.02360    0.02448 =
         0.02259   -0.00188    0.01345    0.00007
AFIX  43
H4    3    0.280254    0.280364    0.802406    11.00000   -1.20000
AFIX   0
C5    2    0.372057    0.013892    0.757954    11.00000    0.02237    0.02186 =
         0.01924    0.00128    0.00978   -0.00086
AFIX  43
H5    3    0.373319   -0.106322    0.821841    11.00000   -1.20000
AFIX   0
C6    2    0.424125   -0.039644    0.673986    11.00000    0.02181    0.01756 =
         0.02225   -0.00077    0.01177   -0.00055
AFIX  43
H6    3    0.456538   -0.200035    0.676890    11.00000   -1.20000
AFIX   0
SIMU 0.003 N2A N2B
PART 1 21.
N2A   1    0.963783    0.078974    0.974573    21.00000    0.04192    0.02994 =
         0.02534    0.00090    0.02099    0.00372
PART 2 -21.
N2B   1    0.987413   -0.096943    0.957803   -21.00000    0.04155    0.03331 =
         0.02374    0.00038    0.02217    0.00067
PART 0
C7    2    0.914726    0.042925    0.833312    11.00000    0.02146    0.04852 =
         0.02045    0.00567    0.00624   -0.00878
C8    2    0.924288   -0.164232    0.760407    11.00000    0.03305    0.02906 =
         0.05392    0.00784    0.02223    0.00192
AFIX  43
H8    3    0.963785   -0.309597    0.802680    11.00000   -1.20000
AFIX   0
C9    2    0.874655   -0.153960    0.623936    11.00000    0.03280    0.03965 =
         0.05357   -0.01817    0.02779   -0.00877
AFIX  43
H9    3    0.881040   -0.292404    0.573164    11.00000   -1.20000
AFIX   0
C10   2    0.815597    0.060663    0.562409    11.00000    0.02295    0.05956 =
         0.02113    0.00116    0.00921   -0.00880
AFIX  43
H10   3    0.781547    0.067365    0.470081    11.00000   -1.20000
AFIX   0
C11   2    0.807075    0.265451    0.637971    11.00000    0.03235    0.03527 =
         0.04736    0.01446    0.02215    0.00682
AFIX  43
H11   3    0.767646    0.411547    0.596624    11.00000   -1.20000
AFIX   0
C12   2    0.855969    0.254943    0.772493    11.00000    0.03618    0.03364 =
         0.03971   -0.00707    0.02683   -0.00771
AFIX  43
H12   3    0.849337    0.392990    0.823340    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0097_bn1 in P2(1)/c
REM wR2 = 0.1941, GooF = S = 1.068, Restrained GooF = 1.067 for all data
REM R1 = 0.0684 for 2740 Fo > 4sig(Fo) and 0.0763 for all 3215 data
REM 138 parameters refined using 6 restraints

END

WGHT      0.1130      0.2310

REM Highest difference peak  0.530,  deepest hole -0.411,  1-sigma level  0.064
Q1    1   0.9325 -0.0385  0.8066  11.00000  0.05    0.53
Q2    1   0.9123 -0.2257  0.7094  11.00000  0.05    0.38
Q3    1   0.3122  0.3245  0.6877  11.00000  0.05    0.34
Q4    1   0.3305  0.1340  0.7424  11.00000  0.05    0.32
Q5    1   0.4274  0.0650  0.6337  11.00000  0.05    0.32
Q6    1   0.8155  0.2316  0.7031  11.00000  0.05    0.30
Q7    1   0.3940  0.2441  0.5795  11.00000  0.05    0.27
Q8    1   0.3679 -0.0125  0.6925  11.00000  0.05    0.26
Q9    1   0.8131  0.1519  0.5970  11.00000  0.05    0.26
Q10   1   0.9172  0.1447  0.8121  11.00000  0.05    0.24
Q11   1   0.5000  0.0000  0.5000  10.50000  0.05    0.24
Q12   1   0.8790 -0.1471  0.6817  11.00000  0.05    0.22
Q13   1   0.9195  0.1442  0.9906  11.00000  0.05    0.22
Q14   1   0.4415  0.0790  0.5381  11.00000  0.05    0.21
Q15   1   0.5084  0.1976  0.4815  11.00000  0.05    0.20
Q16   1   0.3500  0.4401  0.6091  11.00000  0.05    0.19
Q17   1   0.4963  0.1645  0.6735  11.00000  0.05    0.17
Q18   1   0.8696  0.1207  0.8803  11.00000  0.05    0.17
Q19   1   0.8495 -0.0966  0.5719  11.00000  0.05    0.17
Q20   1   0.9070  0.2240  0.8496  11.00000  0.05    0.16
;
_shelx_res_checksum              66840
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_13GPa
_database_code_depnum_ccdc_archive 'CCDC 2336573'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_13GPa           
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.339 Why?  
RESPONSE: Data were collected from a single crystal loaded within a diamond
anvil high-pressure cell. A large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT088_AZO_13GPa           
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.72 Note  
RESPONSE: A large part of reciprocal space was shadowed by the pressure 
cell.
;
_vrf_PLAT149_AZO_13GPa           
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.19 Degree
RESPONSE: Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree.
;
_vrf_PLAT331_AZO_13GPa           
;
PROBLEM: Small Aver Phenyl C-C Dist C7       --C12      .       1.36 Ang.  
RESPONSE: This is due to disorder at the pressure of phase transition.
;
_vrf_PLAT340_AZO_13GPa           
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01425 Ang.  
RESPONSE: A large part of reciprocal space was shadowed by the pressure 
cell.
;
_vrf_PLAT411_AZO_13GPa           
;
PROBLEM: Short Inter H...H Contact  H2       ..H11      .       1.95 Ang.  
RESPONSE: Intermolecular distances are strongly shortened at high 
pressure and atoms approach closer to one another than at ambient 
conditions or low temperature.
;
_vrf_PLAT911_AZO_13GPa           
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        724 Report
RESPONSE: Data were collected from a single crystal loaded within a diamond
anvil high-pressure cell. A large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3s (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-16
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   13.08(3)
_cell_length_b                   5.1368(12)
_cell_length_c                   10.777(9)
_cell_angle_alpha                90
_cell_angle_beta                 112.98(19)
_cell_angle_gamma                90
_cell_volume                     666.4(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       13040000
_cell_measurement_reflns_used    335
_cell_measurement_theta_min      2.1750
_cell_measurement_theta_max      20.0320

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.816
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.21686
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         13040000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    0.50    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0338818166
_diffrn_orient_matrix_UB_12      0.0092082210
_diffrn_orient_matrix_UB_13      -0.0185264091
_diffrn_orient_matrix_UB_21      0.0031797762
_diffrn_orient_matrix_UB_22      0.0226098340
_diffrn_orient_matrix_UB_23      -0.0348004424
_diffrn_orient_matrix_UB_31      -0.0030587996
_diffrn_orient_matrix_UB_32      -0.0757930484
_diffrn_orient_matrix_UB_33      -0.0124267416
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            1326
_diffrn_reflns_av_unetI/netI     0.0843
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.181
_diffrn_reflns_theta_max         20.401
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.228
_diffrn_measured_fraction_theta_full 0.339
_diffrn_reflns_Laue_measured_fraction_max 0.228
_diffrn_reflns_Laue_measured_fraction_full 0.339
_diffrn_reflns_point_group_measured_fraction_max 0.228
_diffrn_reflns_point_group_measured_fraction_full 0.339
_reflns_number_total             783
_reflns_number_gt                513
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal class for the 
 calculation of statistics and refinement. _reflns_Friedel_fraction is 
 defined as the number of unique Friedel pairs measured divided by the number 
 that would be possible theoretically, ignoring centric projections and 
 systematic absences.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          
;
 7 low-resolution reflections, that were affected by beamstop, were removed 
 from refinemet. Some other reflections were removed as outliers. 
The atomic displacement parameters 
of atoms N2A, N2B and C7 were restraint with RIGU keyword in ShelXL input 
('enhanced rigid bond' restraint for all bonds in the connectivity list).
The anisotropic displacement parameters 
of the disordered nitrogen atoms N2A and N2B were restrained to 
similar behaviour using SIMU restraint. The anisotropic displacement 
parameters of all atoms were restrained to isotropic behqaviour using ISOR 
restraint.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         783
_refine_ls_number_parameters     137
_refine_ls_number_restraints     102
_refine_ls_R_factor_all          0.1379
_refine_ls_R_factor_gt           0.1062
_refine_ls_wR_factor_ref         0.3108
_refine_ls_wR_factor_gt          0.2887
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_restrained_S_all      1.203
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.071
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
 
 Least-squares planes (x,y,z in crystal coordinates) and deviations from them
 (* indicates atom used to define plane)
 
 * -0.0064 (0.0100)  C7
 *  0.0176 (0.0117)  C8
 * -0.0190 (0.0117)  C9
 *  0.0089 (0.0100)  C10
 *  0.0032 (0.0111)  C11
 * -0.0043 (0.0109)  C12
    0.5281 (0.0423)  C7_$1
    0.5040 (0.0440)  C8_$1
    0.5407 (0.0422)  C9_$1
    0.5128 (0.0410)  C10_$1
    0.5185 (0.0452)  C11_$1
    0.5259 (0.0406)  C12_$1
 
 Rms deviation of fitted atoms =   0.0117
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4908(10) 0.1172(8) 0.5069(6) 0.027(2) Uani 1 1 d . U . . .
C1 C 0.4273(11) 0.1488(8) 0.5855(7) 0.026(2) Uani 1 1 d . U . . .
C2 C 0.3781(11) 0.3861(8) 0.5805(7) 0.026(2) Uani 1 1 d . U . . .
H2 H 0.383770 0.515884 0.523315 0.031 Uiso 1 1 calc R U . . .
C3 C 0.3206(12) 0.4296(9) 0.6608(8) 0.029(2) Uani 1 1 d . U . . .
H3 H 0.282075 0.585095 0.652703 0.035 Uiso 1 1 calc R U . . .
C4 C 0.3188(11) 0.2460(10) 0.7537(7) 0.030(2) Uani 1 1 d . U . . .
H4 H 0.282641 0.281027 0.810901 0.036 Uiso 1 1 calc R U . . .
C5 C 0.3707(11) 0.0131(9) 0.7605(7) 0.027(2) Uani 1 1 d . U . . .
H5 H 0.369278 -0.110887 0.822702 0.032 Uiso 1 1 calc R U . . .
C6 C 0.4253(12) -0.0423(9) 0.6768(7) 0.025(2) Uani 1 1 d . U . . .
H6 H 0.459790 -0.202365 0.681093 0.030 Uiso 1 1 calc R U . . .
N2A N 0.9641(18) 0.0793(12) 0.9745(13) 0.030(2) Uani 0.67(2) 1 d . U P A 1
N2B N 0.984(4) -0.092(3) 0.954(3) 0.031(3) Uani 0.33(2) 1 d . U P A 2
C7 C 0.9129(15) 0.0395(14) 0.8289(9) 0.048(3) Uani 1 1 d . U . . .
C8 C 0.9231(18) -0.1637(14) 0.7533(12) 0.054(3) Uani 1 1 d . U . . .
H8 H 0.964456 -0.310582 0.793092 0.065 Uiso 1 1 calc R U . . .
C9 C 0.8687(18) -0.1419(12) 0.6133(11) 0.050(3) Uani 1 1 d . U . . .
H9 H 0.869266 -0.280050 0.557769 0.059 Uiso 1 1 calc R U . . .
C10 C 0.8159(15) 0.0792(14) 0.5600(9) 0.045(3) Uani 1 1 d . U . . .
H10 H 0.783284 0.096290 0.466725 0.054 Uiso 1 1 calc R U . . .
C11 C 0.8086(16) 0.2805(12) 0.6387(11) 0.045(2) Uani 1 1 d . U . . .
H11 H 0.770181 0.431435 0.599659 0.054 Uiso 1 1 calc R U . . .
C12 C 0.8581(14) 0.2574(11) 0.7745(9) 0.037(2) Uani 1 1 d . U . . .
H12 H 0.853969 0.392848 0.829650 0.045 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.030(6) 0.0341(17) 0.024(2) -0.0005(14) 0.018(3) 0.001(3)
C1 0.029(6) 0.0312(18) 0.026(3) 0.0022(16) 0.021(4) 0.006(3)
C2 0.027(6) 0.0306(19) 0.026(3) 0.0024(17) 0.018(4) 0.001(3)
C3 0.031(6) 0.0314(18) 0.034(3) -0.0024(18) 0.024(4) -0.001(3)
C4 0.034(6) 0.036(2) 0.027(3) -0.0014(17) 0.020(4) -0.001(3)
C5 0.027(6) 0.034(2) 0.025(3) 0.0026(16) 0.018(4) 0.003(3)
C6 0.027(6) 0.0280(17) 0.025(3) -0.0013(16) 0.016(4) 0.000(3)
N2A 0.033(5) 0.032(2) 0.027(3) 0.002(2) 0.014(3) 0.000(3)
N2B 0.033(5) 0.035(4) 0.028(4) -0.001(3) 0.015(4) 0.000(4)
C7 0.048(6) 0.070(3) 0.034(3) 0.008(2) 0.026(4) -0.010(4)
C8 0.052(7) 0.050(3) 0.066(4) 0.012(3) 0.028(4) 0.002(4)
C9 0.048(7) 0.050(3) 0.054(4) -0.013(2) 0.024(4) 0.007(4)
C10 0.047(7) 0.065(3) 0.035(3) 0.000(2) 0.028(4) -0.013(4)
C11 0.043(7) 0.046(3) 0.050(3) 0.014(2) 0.023(4) 0.001(4)
C12 0.038(6) 0.048(2) 0.038(3) -0.005(2) 0.027(4) -0.004(3)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.248(8) 3_656 ?
N1 C1 1.408(9) . ?
C1 C2 1.369(9) . ?
C1 C6 1.398(6) . ?
C2 C3 1.369(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.363(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2A N2A 1.20(3) 3_757 ?
N2A C7 1.461(17) . ?
N2B N2B 1.31(5) 3_757 ?
N2B C7 1.47(4) . ?
C7 C12 1.335(15) . ?
C7 C8 1.362(10) . ?
C8 C9 1.399(19) . ?
C8 H8 0.9300 . ?
C9 C10 1.337(15) . ?
C9 H9 0.9300 . ?
C10 C11 1.364(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.355(15) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 111.7(6) 3_656 . ?
C2 C1 C6 121.0(6) . . ?
C2 C1 N1 117.2(4) . . ?
C6 C1 N1 121.3(7) . . ?
C1 C2 C3 119.1(4) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 121.0(7) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.3(6) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.2(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 118.2(6) . . ?
C5 C6 H6 120.9 . . ?
C1 C6 H6 120.9 . . ?
N2A N2A C7 110.2(11) 3_757 . ?
N2B N2B C7 105(2) 3_757 . ?
C12 C7 C8 122.8(9) . . ?
C12 C7 N2A 107.3(7) . . ?
C8 C7 N2A 129.7(12) . . ?
C12 C7 N2B 145.7(9) . . ?
C8 C7 N2B 91.3(11) . . ?
C7 C8 C9 117.2(11) . . ?
C7 C8 H8 121.4 . . ?
C9 C8 H8 121.4 . . ?
C10 C9 C8 119.4(6) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 121.8(9) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C12 C11 C10 119.0(10) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C7 C12 C11 119.7(6) . . ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -164.0(13) 3_656 . . . ?
N1 N1 C1 C6 23.4(18) 3_656 . . . ?
C6 C1 C2 C3 -4.0(18) . . . . ?
N1 C1 C2 C3 -176.5(11) . . . . ?
C1 C2 C3 C4 5.1(18) . . . . ?
C2 C3 C4 C5 -3.3(19) . . . . ?
C3 C4 C5 C6 0(2) . . . . ?
C4 C5 C6 C1 0.8(19) . . . . ?
C2 C1 C6 C5 1.1(18) . . . . ?
N1 C1 C6 C5 173.3(10) . . . . ?
N2A N2A C7 C12 -162.8(17) 3_757 . . . ?
N2A N2A C7 C8 11(3) 3_757 . . . ?
N2B N2B C7 C12 -13(6) 3_757 . . . ?
N2B N2B C7 C8 162(4) 3_757 . . . ?
C12 C7 C8 C9 -3(2) . . . . ?
N2A C7 C8 C9 -176.3(16) . . . . ?
N2B C7 C8 C9 -179.3(19) . . . . ?
C7 C8 C9 C10 4(2) . . . . ?
C8 C9 C10 C11 -3(2) . . . . ?
C9 C10 C11 C12 1(2) . . . . ?
C8 C7 C12 C11 1(2) . . . . ?
N2A C7 C12 C11 175.6(14) . . . . ?
N2B C7 C12 C11 174(3) . . . . ?
C10 C11 C12 C7 0(2) . . . . ?


_shelx_res_file                  
;
TITL sample_0117_bn1 in P2(1)/c
    sample_0117_bn1.res
    created by SHELXL-2018/3 at 23:03:45 on 24-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  13.076086   5.136844  10.776788  90.0000 112.9758  90.0000
ZERR    4.00   0.032000   0.001151   0.009481   0.0000   0.1938   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
SIMU 0.005 0.01 2 N2A N2B
rigU 0.005 0.01 N2A N2B C7
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
EQIV $1 -x+2, -y, -z+2
MPLA 6 C7 C8 C9 C10 C11 C12 C7_$1 C8_$1 C9_$1 C10_$1 C11_$1 C12_$1
FMAP 2
PLAN 20
WGHT    0.200000
FVAR      24.44904   0.66524
N1    1    0.490819    0.117172    0.506916    11.00000    0.02954    0.03405 =
         0.02355   -0.00048    0.01815    0.00124
C1    2    0.427314    0.148797    0.585459    11.00000    0.02943    0.03119 =
         0.02621    0.00222    0.02083    0.00583
C2    2    0.378141    0.386077    0.580476    11.00000    0.02687    0.03057 =
         0.02647    0.00235    0.01799    0.00120
AFIX  43
H2    3    0.383770    0.515884    0.523315    11.00000   -1.20000
AFIX   0
C3    2    0.320585    0.429606    0.660775    11.00000    0.03109    0.03137 =
         0.03407   -0.00242    0.02358   -0.00061
AFIX  43
H3    3    0.282075    0.585095    0.652703    11.00000   -1.20000
AFIX   0
C4    2    0.318833    0.246014    0.753651    11.00000    0.03379    0.03624 =
         0.02680   -0.00135    0.02026   -0.00077
AFIX  43
H4    3    0.282641    0.281027    0.810901    11.00000   -1.20000
AFIX   0
C5    2    0.370696    0.013071    0.760497    11.00000    0.02742    0.03424 =
         0.02521    0.00255    0.01781    0.00323
AFIX  43
H5    3    0.369278   -0.110887    0.822702    11.00000   -1.20000
AFIX   0
C6    2    0.425309   -0.042337    0.676800    11.00000    0.02663    0.02796 =
         0.02543   -0.00129    0.01590    0.00018
AFIX  43
H6    3    0.459790   -0.202365    0.681093    11.00000   -1.20000
AFIX   0
rem SIMU 0.003 C7 > C12

PART 1 21.
N2A   1    0.964075    0.079267    0.974535    21.00000    0.03344    0.03230 =
         0.02702    0.00185    0.01449    0.00023
PART 2 -21.
N2B   1    0.983795   -0.092372    0.954456   -21.00000    0.03305    0.03523 =
         0.02822   -0.00143    0.01537    0.00024
PART 0
C7    2    0.912873    0.039529    0.828871    11.00000    0.04775    0.07000 =
         0.03388    0.00790    0.02579   -0.01047
C8    2    0.923092   -0.163663    0.753308    11.00000    0.05174    0.04956 =
         0.06587    0.01229    0.02816    0.00235
AFIX  43
H8    3    0.964456   -0.310582    0.793092    11.00000   -1.20000
AFIX   0
C9    2    0.868699   -0.141904    0.613274    11.00000    0.04823    0.05025 =
         0.05361   -0.01267    0.02378    0.00675
AFIX  43
H9    3    0.869266   -0.280050    0.557769    11.00000   -1.20000
AFIX   0
C10   2    0.815907    0.079234    0.559977    11.00000    0.04675    0.06460 =
         0.03529   -0.00040    0.02789   -0.01257
AFIX  43
H10   3    0.783284    0.096290    0.466725    11.00000   -1.20000
AFIX   0
C11   2    0.808591    0.280547    0.638666    11.00000    0.04308    0.04622 =
         0.05019    0.01357    0.02307    0.00078
AFIX  43
H11   3    0.770181    0.431435    0.599659    11.00000   -1.20000
AFIX   0
C12   2    0.858120    0.257432    0.774527    11.00000    0.03763    0.04785 =
         0.03833   -0.00491    0.02748   -0.00369
AFIX  43
H12   3    0.853969    0.392848    0.829650    11.00000   -1.20000
AFIX   0
HKLF 4




REM  sample_0117_bn1 in P2(1)/c
REM wR2 = 0.3108, GooF = S = 1.180, Restrained GooF = 1.203 for all data
REM R1 = 0.1062 for 513 Fo > 4sig(Fo) and 0.1379 for all 783 data
REM 137 parameters refined using 102 restraints

END

WGHT      0.2000      0.0000

REM Highest difference peak  0.282,  deepest hole -0.281,  1-sigma level  0.071
Q1    1   0.9903 -0.1502  0.8190  11.00000  0.05    0.28
Q2    1   0.3237  0.1549  0.5185  11.00000  0.05    0.23
Q3    1   0.7931  0.5444  0.6475  11.00000  0.05    0.23
Q4    1   0.9971  0.1895  0.8600  11.00000  0.05    0.23
Q5    1   0.4081  0.0556  0.6133  11.00000  0.05    0.23
Q6    1   0.4377 -0.3693  0.7526  11.00000  0.05    0.22
Q7    1   0.4077 -0.2554  0.6300  11.00000  0.05    0.22
Q8    1   0.4994  0.1502  0.6518  11.00000  0.05    0.21
Q9    1   0.8316 -0.4805  0.5586  11.00000  0.05    0.20
Q10   1   0.4165  0.2278  0.6010  11.00000  0.05    0.20
Q11   1   0.7511 -0.0949  0.5206  11.00000  0.05    0.20
Q12   1   0.2683  0.1193  0.7316  11.00000  0.05    0.19
Q13   1   0.2846  0.3868  0.5078  11.00000  0.05    0.19
Q14   1   1.0121 -0.4477  0.7799  11.00000  0.05    0.18
Q15   1   0.9519  0.4771  0.9693  11.00000  0.05    0.18
Q16   1   0.9168  0.2411  0.9508  11.00000  0.05    0.18
Q17   1   1.0000  0.5000  1.0000  10.50000  0.05    0.18
Q18   1   0.7323  0.0799  0.4702  11.00000  0.05    0.17
Q19   1   0.4891  0.5284  0.6309  11.00000  0.05    0.17
Q20   1   0.3346  0.1693  0.9168  11.00000  0.05    0.17
;
_shelx_res_checksum              60219
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_0p3GPa
_database_code_depnum_ccdc_archive 'CCDC 2336564'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_0p3GPa          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.337 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT149_AZO_0p3GPa          
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.06 Degree
RESPONSE: Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree.
;
_vrf_PLAT911_AZO_0p3GPa          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        741 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3q (K.Radacki, 2005-22)'
_audit_creation_date             2023-03-15
_shelx_SHELXL_version_number     2018/3

loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   14.998(11)
_cell_length_b                   5.6940(3)
_cell_length_c                   11.992(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.43(6)
_cell_angle_gamma                90
_cell_volume                     946.6(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       306000
_cell_measurement_reflns_used    397
_cell_measurement_theta_min      2.1160
_cell_measurement_theta_max      19.1300

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.00293
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 Crystals were grown from saturated solution. For data collection the crystal 
 was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         306000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    0.50    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.0293809802
_diffrn_orient_matrix_UB_12      0.0061315657
_diffrn_orient_matrix_UB_13      0.0173252956
_diffrn_orient_matrix_UB_21      -0.0034319108
_diffrn_orient_matrix_UB_22      0.0192069222
_diffrn_orient_matrix_UB_23      0.0310371750
_diffrn_orient_matrix_UB_31      0.0016335794
_diffrn_orient_matrix_UB_32      -0.0690674125
_diffrn_orient_matrix_UB_33      0.0101689127
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            4294
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.960
_diffrn_reflns_theta_max         21.393
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.208
_diffrn_measured_fraction_theta_full 0.337
_diffrn_reflns_Laue_measured_fraction_max 0.208
_diffrn_reflns_Laue_measured_fraction_full 0.337
_diffrn_reflns_point_group_measured_fraction_max 0.208
_diffrn_reflns_point_group_measured_fraction_full 0.337
_reflns_number_total             4294
_reflns_number_gt                3112
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
The BASF parameter was refined to 46.3%. The anisotropic displacement 
parameters of the disordered nitrogen atoms N2A and N2B were restrained to 
similar behaviour using SIMU restraint. The anisotropic displacement 
parameters of all atoms were restrained to isotropic behqaviour using ISOR 
restraint.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0973P)²+0.0247P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4294
_refine_ls_number_parameters     138
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1784
_refine_ls_wR_factor_gt          0.1652
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.036
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4892(3) 0.1040(3) 0.5043(2) 0.0396(12) Uani 1 1 d . U . . .
C1 C 0.4321(3) 0.1368(3) 0.5749(2) 0.0344(13) Uani 1 1 d . U . . .
C2 C 0.3843(4) 0.3491(4) 0.5611(3) 0.0416(14) Uani 1 1 d . U . . .
H2 H 0.390557 0.461231 0.508166 0.050 Uiso 1 1 calc R U . . .
C3 C 0.3273(4) 0.3949(4) 0.6258(3) 0.0464(15) Uani 1 1 d . U . . .
H3 H 0.293468 0.535551 0.614439 0.056 Uiso 1 1 calc R U . . .
C4 C 0.3207(4) 0.2302(4) 0.7082(3) 0.0460(16) Uani 1 1 d . U . . .
H4 H 0.282740 0.260661 0.752370 0.055 Uiso 1 1 calc R U . . .
C5 C 0.3708(4) 0.0216(4) 0.7239(3) 0.0423(15) Uani 1 1 d . U . . .
H5 H 0.366936 -0.086966 0.779847 0.051 Uiso 1 1 calc R U . . .
C6 C 0.4266(3) -0.0293(3) 0.6581(3) 0.0364(13) Uani 1 1 d . U . . .
H6 H 0.459748 -0.170860 0.668911 0.044 Uiso 1 1 calc R U . . .
N2A N 0.9695(6) 0.0759(5) 0.9770(7) 0.048(2) Uani 0.877(19) 1 d . U P A 1
N2B N 0.995(4) -0.085(4) 0.961(5) 0.050(4) Uani 0.123(19) 1 d . U P A 2
C7 C 0.9197(4) 0.0505(5) 0.8490(3) 0.0495(18) Uani 1 1 d . U . . .
C8 C 0.9284(5) -0.1375(5) 0.7792(4) 0.0549(18) Uani 1 1 d . U . . .
H8 H 0.968891 -0.263109 0.814738 0.066 Uiso 1 1 calc R U . . .
C9 C 0.8756(5) -0.1335(5) 0.6565(4) 0.060(2) Uani 1 1 d . U . . .
H9 H 0.880067 -0.258671 0.609064 0.071 Uiso 1 1 calc R U . . .
C10 C 0.8162(5) 0.0535(6) 0.6032(4) 0.057(2) Uani 1 1 d . U . . .
H10 H 0.781356 0.055266 0.520302 0.068 Uiso 1 1 calc R U . . .
C11 C 0.8090(5) 0.2381(5) 0.6739(4) 0.061(2) Uani 1 1 d . U . . .
H11 H 0.769340 0.365140 0.638272 0.073 Uiso 1 1 calc R U . . .
C12 C 0.8593(5) 0.2355(5) 0.7950(3) 0.056(2) Uani 1 1 d . U . . .
H12 H 0.852906 0.359397 0.841936 0.067 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.046(4) 0.0382(9) 0.0407(16) 0.0007(7) 0.023(2) 0.0036(10)
C1 0.035(4) 0.0360(10) 0.0332(16) -0.0025(8) 0.014(2) -0.0003(11)
C2 0.046(5) 0.0385(11) 0.0424(19) 0.0027(8) 0.019(3) 0.0061(12)
C3 0.045(5) 0.0423(12) 0.055(2) -0.0032(10) 0.023(3) 0.0084(13)
C4 0.042(5) 0.0544(14) 0.050(2) -0.0079(11) 0.026(3) -0.0013(14)
C5 0.043(5) 0.0499(13) 0.038(2) 0.0000(9) 0.020(3) -0.0048(13)
C6 0.037(4) 0.0373(10) 0.0372(18) 0.0012(8) 0.016(3) 0.0018(11)
N2A 0.049(6) 0.0522(14) 0.044(4) 0.0024(13) 0.019(4) 0.0073(16)
N2B 0.050(8) 0.055(5) 0.044(6) -0.001(5) 0.016(8) 0.006(5)
C7 0.046(6) 0.0611(15) 0.045(2) 0.0065(11) 0.021(3) -0.0031(17)
C8 0.051(6) 0.0550(15) 0.062(3) 0.0060(12) 0.025(4) 0.0042(16)
C9 0.060(7) 0.0633(17) 0.062(3) -0.0134(14) 0.030(4) -0.0071(18)
C10 0.047(7) 0.078(2) 0.044(3) 0.0027(14) 0.017(4) -0.004(2)
C11 0.059(7) 0.0647(17) 0.062(3) 0.0155(14) 0.027(4) 0.0139(19)
C12 0.059(6) 0.0593(15) 0.052(3) 0.0008(12) 0.026(4) 0.0043(17)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.243(4) 3_656 ?
N1 C1 1.426(4) . ?
C1 C2 1.383(4) . ?
C1 C6 1.400(3) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2A N2A 1.227(13) 3_757 ?
N2A C7 1.435(10) . ?
N2B N2B 1.31(7) 3_757 ?
N2B C7 1.59(6) . ?
C7 C12 1.380(6) . ?
C7 C8 1.394(4) . ?
C8 C9 1.380(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.357(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 114.2(2) 3_656 . ?
C2 C1 C6 120.4(2) . . ?
C2 C1 N1 116.41(18) . . ?
C6 C1 N1 123.1(2) . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.3(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 118.6(2) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
N2A N2A C7 113.9(6) 3_757 . ?
N2B N2B C7 96(4) 3_757 . ?
C12 C7 C8 120.0(4) . . ?
C12 C7 N2A 113.9(3) . . ?
C8 C7 N2A 126.1(4) . . ?
C12 C7 N2B 153.6(12) . . ?
C8 C7 N2B 86.5(12) . . ?
C9 C8 C7 118.7(4) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.5(4) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 120.4(4) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C7 120.5(3) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -162.9(5) 3_656 . . . ?
N1 N1 C1 C6 19.7(7) 3_656 . . . ?
C6 C1 C2 C3 -2.7(6) . . . . ?
N1 C1 C2 C3 179.8(4) . . . . ?
C1 C2 C3 C4 2.2(7) . . . . ?
C2 C3 C4 C5 -0.4(7) . . . . ?
C3 C4 C5 C6 -0.9(6) . . . . ?
C4 C5 C6 C1 0.4(6) . . . . ?
C2 C1 C6 C5 1.4(6) . . . . ?
N1 C1 C6 C5 178.6(4) . . . . ?
N2A N2A C7 C12 -172.8(6) 3_757 . . . ?
N2A N2A C7 C8 6.8(10) 3_757 . . . ?
N2B N2B C7 C12 -7(7) 3_757 . . . ?
N2B N2B C7 C8 173(4) 3_757 . . . ?
C12 C7 C8 C9 0.0(7) . . . . ?
N2A C7 C8 C9 -179.6(5) . . . . ?
N2B C7 C8 C9 -179.9(16) . . . . ?
C7 C8 C9 C10 0.8(7) . . . . ?
C8 C9 C10 C11 -0.6(7) . . . . ?
C9 C10 C11 C12 -0.4(7) . . . . ?
C10 C11 C12 C7 1.2(8) . . . . ?
C8 C7 C12 C11 -1.0(7) . . . . ?
N2A C7 C12 C11 178.6(5) . . . . ?
N2B C7 C12 C11 179(3) . . . . ?


_shelx_res_file                  
;
TITL sample_0013_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 19:26:07 on 23-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  14.997991   5.693984  11.991761  90.0000 112.4305  90.0000
ZERR    4.00   0.011433   0.000288   0.003415   0.0000   0.0613   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
OMIT 8 -8 -4
OMIT 3 -1 -1
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.03
FMAP 2
PLAN 20
WGHT    0.097300    0.024700
BASF   0.46254
FVAR      22.61195   0.87739
N1    1    0.489157    0.103995    0.504345    11.00000    0.04582    0.03824 =
         0.04067    0.00066    0.02314    0.00355
C1    2    0.432130    0.136783    0.574868    11.00000    0.03523    0.03599 =
         0.03317   -0.00248    0.01448   -0.00029
C2    2    0.384320    0.349097    0.561115    11.00000    0.04586    0.03851 =
         0.04236    0.00272    0.01907    0.00607
AFIX  43
H2    3    0.390557    0.461231    0.508166    11.00000   -1.20000
AFIX   0
C3    2    0.327350    0.394945    0.625825    11.00000    0.04479    0.04233 =
         0.05548   -0.00324    0.02282    0.00836
AFIX  43
H3    3    0.293468    0.535551    0.614439    11.00000   -1.20000
AFIX   0
C4    2    0.320711    0.230170    0.708218    11.00000    0.04171    0.05439 =
         0.04953   -0.00789    0.02601   -0.00132
AFIX  43
H4    3    0.282740    0.260661    0.752370    11.00000   -1.20000
AFIX   0
C5    2    0.370787    0.021580    0.723907    11.00000    0.04255    0.04993 =
         0.03848   -0.00001    0.01991   -0.00480
AFIX  43
H5    3    0.366936   -0.086966    0.779847    11.00000   -1.20000
AFIX   0
C6    2    0.426581   -0.029287    0.658117    11.00000    0.03658    0.03734 =
         0.03718    0.00120    0.01631    0.00175
AFIX  43
H6    3    0.459748   -0.170860    0.668911    11.00000   -1.20000
AFIX   0
REM SIMU 0.003 C7 > C12
SIMU 0.003 N2A N2B
PART 1 21.
N2A   1    0.969454    0.075877    0.976975    21.00000    0.04916    0.05221 =
         0.04433    0.00236    0.01867    0.00725
PART 2 -21.
N2B   1    0.994871   -0.084691    0.961266   -21.00000    0.05049    0.05472 =
         0.04386   -0.00057    0.01620    0.00576
PART 0
C7    2    0.919739    0.050463    0.848973    11.00000    0.04592    0.06109 =
         0.04493    0.00650    0.02119   -0.00310
C8    2    0.928356   -0.137498    0.779232    11.00000    0.05063    0.05505 =
         0.06199    0.00599    0.02470    0.00417
AFIX  43
H8    3    0.968891   -0.263109    0.814738    11.00000   -1.20000
AFIX   0
C9    2    0.875552   -0.133518    0.656465    11.00000    0.06004    0.06330 =
         0.06161   -0.01342    0.03027   -0.00714
AFIX  43
H9    3    0.880067   -0.258671    0.609064    11.00000   -1.20000
AFIX   0
C10   2    0.816218    0.053486    0.603192    11.00000    0.04707    0.07846 =
         0.04389    0.00270    0.01660   -0.00393
AFIX  43
H10   3    0.781356    0.055266    0.520302    11.00000   -1.20000
AFIX   0
C11   2    0.808960    0.238114    0.673873    11.00000    0.05931    0.06466 =
         0.06203    0.01549    0.02729    0.01386
AFIX  43
H11   3    0.769340    0.365140    0.638272    11.00000   -1.20000
AFIX   0
C12   2    0.859259    0.235489    0.794976    11.00000    0.05938    0.05934 =
         0.05248    0.00077    0.02575    0.00433
AFIX  43
H12   3    0.852906    0.359397    0.841936    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0013_bn1 in P2(1)/c
REM wR2 = 0.1784, GooF = S = 1.078, Restrained GooF = 1.067 for all data
REM R1 = 0.0591 for 3112 Fo > 4sig(Fo) and 0.0795 for all 4294 data
REM 138 parameters refined using 96 restraints

END

WGHT      0.0973      0.0247

REM Highest difference peak  0.184,  deepest hole -0.162,  1-sigma level  0.036
Q1    1   0.4169  0.2445  0.5907  11.00000  0.05    0.18
Q2    1   0.9234 -0.0545  0.8263  11.00000  0.05    0.18
Q3    1   0.3335  0.3118  0.6680  11.00000  0.05    0.17
Q4    1   0.4404  0.0737  0.6302  11.00000  0.05    0.17
Q5    1   0.4209  0.0253  0.7076  11.00000  0.05    0.16
Q6    1   0.9700  0.1117  0.8704  11.00000  0.05    0.15
Q7    1   0.3193  0.1085  0.6915  11.00000  0.05    0.14
Q8    1   0.4973  0.2275  0.4824  11.00000  0.05    0.13
Q9    1   0.3817  0.1538  0.7467  11.00000  0.05    0.12
Q10   1   0.9276  0.1530  0.8306  11.00000  0.05    0.12
Q11   1   0.9534  0.0698  0.9076  11.00000  0.05    0.12
Q12   1   0.9384 -0.2526  1.0016  11.00000  0.05    0.12
Q13   1   0.8110  0.0543  0.4529  11.00000  0.05    0.12
Q14   1   0.7895  0.0780  0.6376  11.00000  0.05    0.11
Q15   1   0.8881  0.2895  0.9916  11.00000  0.05    0.11
Q16   1   0.3701  0.3611  0.6097  11.00000  0.05    0.10
Q17   1   0.4435  0.1052  0.5174  11.00000  0.05    0.10
Q18   1   0.8315  0.1465  0.6487  11.00000  0.05    0.10
Q19   1   0.4237  0.4719  0.6664  11.00000  0.05    0.10
Q20   1   0.3200  0.3142  0.5695  11.00000  0.05    0.10
;
_shelx_res_checksum              87818
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_12GPa
_database_code_depnum_ccdc_archive 'CCDC 2336571'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_12GPa           
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.337 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT149_AZO_12GPa           
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.10 Degree
RESPONSE: Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree.
;
_vrf_PLAT331_AZO_12GPa           
;
PROBLEM: Small Aver Phenyl C-C Dist C7       --C12      .       1.36 Ang.  
RESPONSE: This is due to disorder, which is increasing close to the 
high-pressure phase transition.
;
_vrf_PLAT411_AZO_12GPa           
;
PROBLEM: Short Inter H...H Contact  H2       ..H11      .       1.93 Ang.  
RESPONSE: Intermolecular distances are strongly shortened at high 
pressure and atoms approach closer to one another than at ambient 
conditions or low temperature.
;
_vrf_PLAT911_AZO_12GPa           
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        574 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3r (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-16
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   13.111(17)
_cell_length_b                   5.1676(4)
_cell_length_c                   10.860(5)
_cell_angle_alpha                90
_cell_angle_beta                 113.15(10)
_cell_angle_gamma                90
_cell_volume                     676.5(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       11950000
_cell_measurement_reflns_used    484
_cell_measurement_theta_min      2.3490
_cell_measurement_theta_max      21.0420

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.789
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.39832
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         11950000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    0.50    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0339144871
_diffrn_orient_matrix_UB_12      0.0072820282
_diffrn_orient_matrix_UB_13      -0.0186020514
_diffrn_orient_matrix_UB_21      0.0029840613
_diffrn_orient_matrix_UB_22      0.0220137758
_diffrn_orient_matrix_UB_23      -0.0346699936
_diffrn_orient_matrix_UB_31      -0.0023104344
_diffrn_orient_matrix_UB_32      -0.0756945436
_diffrn_orient_matrix_UB_33      -0.0117524103
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2814
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.164
_diffrn_reflns_theta_max         21.708
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.193
_diffrn_measured_fraction_theta_full 0.337
_diffrn_reflns_Laue_measured_fraction_max 0.193
_diffrn_reflns_Laue_measured_fraction_full 0.337
_diffrn_reflns_point_group_measured_fraction_max 0.193
_diffrn_reflns_point_group_measured_fraction_full 0.337
_reflns_number_total             2814
_reflns_number_gt                2017
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
The BASF parameter was refined to 22%. A low-resolution reflection affected 
by beamstop [1 1 -1] was removed from refinement. Some other 
reflections were removed as outliers. The atomic displacement parameters 
of atoms N2A, N2B and C7 were restraint with RIGU keyword in ShelXL input 
('enhanced rigid bond' restraint for all bonds in the connectivity list).
The anisotropic displacement parameters 
of the disordered nitrogen atoms N2A and N2B were restrained to 
similar behaviour using SIMU restraint. The anisotropic displacement 
parameters of all atoms were restrained to isotropic behqaviour using ISOR 
restraint.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1339P)²+0.1141P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2814
_refine_ls_number_parameters     138
_refine_ls_number_restraints     102
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0765
_refine_ls_wR_factor_ref         0.2379
_refine_ls_wR_factor_gt          0.2242
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.163
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.074
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4896(6) 0.1164(5) 0.5067(4) 0.0205(19) Uani 1 1 d . U . . .
C1 C 0.4276(7) 0.1478(6) 0.5852(4) 0.019(2) Uani 1 1 d . U . . .
C2 C 0.3774(7) 0.3839(6) 0.5787(5) 0.020(2) Uani 1 1 d . U . . .
H2 H 0.382424 0.511623 0.521025 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3197(7) 0.4292(6) 0.6582(5) 0.023(2) Uani 1 1 d . U . . .
H3 H 0.281723 0.584458 0.650251 0.027 Uiso 1 1 calc R U . . .
C4 C 0.3175(7) 0.2457(6) 0.7500(5) 0.022(2) Uani 1 1 d . U . . .
H4 H 0.279882 0.279183 0.805176 0.026 Uiso 1 1 calc R U . . .
C5 C 0.3714(7) 0.0135(6) 0.7591(5) 0.021(2) Uani 1 1 d . U . . .
H5 H 0.372335 -0.107713 0.822870 0.025 Uiso 1 1 calc R U . . .
C6 C 0.4239(7) -0.0403(6) 0.6745(5) 0.020(2) Uani 1 1 d . U . . .
H6 H 0.456548 -0.201058 0.677130 0.024 Uiso 1 1 calc R U . . .
N2A N 0.9633(14) 0.0813(11) 0.9739(13) 0.028(3) Uani 0.67(2) 1 d . U P A 1
N2B N 0.986(3) -0.096(2) 0.958(3) 0.027(3) Uani 0.33(2) 1 d . U P A 2
C7 C 0.9134(9) 0.0399(10) 0.8305(6) 0.037(3) Uani 1 1 d . U . . .
C8 C 0.9224(10) -0.1626(9) 0.7546(8) 0.043(3) Uani 1 1 d . U . . .
H8 H 0.961517 -0.310943 0.794855 0.052 Uiso 1 1 calc R U . . .
C9 C 0.8728(10) -0.1428(9) 0.6176(7) 0.039(3) Uani 1 1 d . U . . .
H9 H 0.877585 -0.278197 0.563746 0.047 Uiso 1 1 calc R U . . .
C10 C 0.8167(10) 0.0754(10) 0.5619(6) 0.040(3) Uani 1 1 d . U . . .
H10 H 0.783275 0.089552 0.469117 0.049 Uiso 1 1 calc R U . . .
C11 C 0.8084(9) 0.2766(8) 0.6401(7) 0.037(2) Uani 1 1 d . U . . .
H11 H 0.769353 0.425443 0.600487 0.044 Uiso 1 1 calc R U . . .
C12 C 0.8568(9) 0.2573(8) 0.7738(6) 0.034(2) Uani 1 1 d . U . . .
H12 H 0.851511 0.392679 0.827409 0.040 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.021(6) 0.0237(13) 0.020(2) -0.0016(10) 0.011(3) -0.0003(16)
C1 0.019(6) 0.0229(14) 0.019(2) -0.0007(11) 0.010(4) 0.0010(19)
C2 0.018(7) 0.0236(15) 0.020(2) 0.0001(12) 0.009(4) -0.0011(18)
C3 0.021(7) 0.0234(14) 0.026(3) -0.0010(13) 0.011(4) 0.003(2)
C4 0.019(7) 0.0278(16) 0.022(2) -0.0019(12) 0.011(4) -0.0003(19)
C5 0.018(7) 0.0271(16) 0.019(3) 0.0011(12) 0.009(4) -0.0003(19)
C6 0.020(6) 0.0215(13) 0.021(2) -0.0005(12) 0.010(4) -0.0001(19)
N2A 0.028(7) 0.035(2) 0.024(4) 0.004(2) 0.015(5) 0.008(3)
N2B 0.028(8) 0.036(5) 0.024(6) 0.000(4) 0.016(6) -0.005(5)
C7 0.027(8) 0.060(3) 0.025(3) 0.0079(19) 0.010(5) -0.010(3)
C8 0.029(8) 0.038(2) 0.066(4) 0.014(2) 0.022(5) 0.002(3)
C9 0.026(8) 0.045(2) 0.055(4) -0.018(2) 0.024(5) -0.007(3)
C10 0.037(9) 0.062(3) 0.028(3) 0.002(2) 0.019(5) -0.009(3)
C11 0.026(8) 0.039(2) 0.051(4) 0.015(2) 0.021(5) 0.006(3)
C12 0.030(8) 0.042(2) 0.040(3) -0.0104(17) 0.026(5) -0.011(3)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.254(6) 3_656 ?
N1 C1 1.400(6) . ?
C1 C2 1.375(6) . ?
C1 C6 1.387(4) . ?
C2 C3 1.373(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2A N2A 1.24(3) 3_757 ?
N2A C7 1.448(15) . ?
N2B N2B 1.30(4) 3_757 ?
N2B C7 1.51(3) . ?
C7 C12 1.354(10) . ?
C7 C8 1.366(8) . ?
C8 C9 1.373(12) . ?
C8 H8 0.9300 . ?
C9 C10 1.353(11) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.340(10) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 112.7(4) 3_656 . ?
C2 C1 C6 120.6(4) . . ?
C2 C1 N1 116.9(3) . . ?
C6 C1 N1 122.2(4) . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.5(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.6(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.3(4) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
N2A N2A C7 109.5(9) 3_757 . ?
N2B N2B C7 101(2) 3_757 . ?
C12 C7 C8 121.5(6) . . ?
C12 C7 N2A 107.6(5) . . ?
C8 C7 N2A 130.7(8) . . ?
C12 C7 N2B 147.1(7) . . ?
C8 C7 N2B 91.3(8) . . ?
C7 C8 C9 118.7(7) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C10 C9 C8 119.3(4) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 121.0(6) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 119.6(6) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C7 119.8(4) . . ?
C11 C12 H12 120.1 . . ?
C7 C12 H12 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -164.2(8) 3_656 . . . ?
N1 N1 C1 C6 21.2(11) 3_656 . . . ?
C6 C1 C2 C3 -2.4(11) . . . . ?
N1 C1 C2 C3 -177.1(7) . . . . ?
C1 C2 C3 C4 3.9(11) . . . . ?
C2 C3 C4 C5 -1.6(11) . . . . ?
C3 C4 C5 C6 -2.3(11) . . . . ?
C4 C5 C6 C1 3.8(11) . . . . ?
C2 C1 C6 C5 -1.5(11) . . . . ?
N1 C1 C6 C5 173.0(6) . . . . ?
N2A N2A C7 C12 -163.5(12) 3_757 . . . ?
N2A N2A C7 C8 12(2) 3_757 . . . ?
N2B N2B C7 C12 -13(4) 3_757 . . . ?
N2B N2B C7 C8 163(2) 3_757 . . . ?
C12 C7 C8 C9 0.1(14) . . . . ?
N2A C7 C8 C9 -174.6(10) . . . . ?
N2B C7 C8 C9 -177.1(12) . . . . ?
C7 C8 C9 C10 0.2(14) . . . . ?
C8 C9 C10 C11 -0.3(13) . . . . ?
C9 C10 C11 C12 0.2(14) . . . . ?
C10 C11 C12 C7 0.0(14) . . . . ?
C8 C7 C12 C11 -0.1(14) . . . . ?
N2A C7 C12 C11 175.7(9) . . . . ?
N2B C7 C12 C11 175(2) . . . . ?


_shelx_res_file                  
;
TITL sample_0109_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 22:57:32 on 24-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  13.111404   5.167608  10.859791  90.0000 113.1507  90.0000
ZERR    4.00   0.016634   0.000442   0.004986   0.0000   0.1013   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
OMIT 1 1 -1
OMIT 0 -1 4
OMIT 2 2 -2
OMIT 2 2 -3
OMIT -1 -2 2
SIMU 0.005 0.01 2 N2A N2B
rigU 0.005 0.01 N2A N2B C7
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.133900    0.114100
BASF   0.22036
FVAR      23.49958   0.67388
N1    1    0.489650    0.116364    0.506665    11.00000    0.02074    0.02367 =
         0.01979   -0.00160    0.01092   -0.00028
C1    2    0.427619    0.147830    0.585197    11.00000    0.01896    0.02289 =
         0.01923   -0.00070    0.01049    0.00103
C2    2    0.377378    0.383884    0.578692    11.00000    0.01801    0.02361 =
         0.01997    0.00011    0.00883   -0.00106
AFIX  43
H2    3    0.382424    0.511623    0.521025    11.00000   -1.20000
AFIX   0
C3    2    0.319670    0.429210    0.658177    11.00000    0.02052    0.02344 =
         0.02619   -0.00103    0.01138    0.00258
AFIX  43
H3    3    0.281723    0.584458    0.650251    11.00000   -1.20000
AFIX   0
C4    2    0.317516    0.245723    0.750000    11.00000    0.01867    0.02782 =
         0.02225   -0.00192    0.01125   -0.00030
AFIX  43
H4    3    0.279882    0.279183    0.805176    11.00000   -1.20000
AFIX   0
C5    2    0.371397    0.013519    0.759142    11.00000    0.01789    0.02714 =
         0.01922    0.00114    0.00863   -0.00032
AFIX  43
H5    3    0.372335   -0.107713    0.822870    11.00000   -1.20000
AFIX   0
C6    2    0.423895   -0.040267    0.674501    11.00000    0.01969    0.02154 =
         0.02088   -0.00053    0.00987   -0.00012
AFIX  43
H6    3    0.456548   -0.201058    0.677130    11.00000   -1.20000
AFIX   0
rem SIMU 0.003 C7 > C12

PART 1 21.
N2A   1    0.963261    0.081310    0.973879    21.00000    0.02818    0.03476 =
         0.02430    0.00399    0.01464    0.00779
PART 2 -21.
N2B   1    0.986067   -0.096176    0.957681   -21.00000    0.02753    0.03609 =
         0.02369    0.00009    0.01596   -0.00487
PART 0
C7    2    0.913375    0.039872    0.830544    11.00000    0.02687    0.06015 =
         0.02504    0.00794    0.00998   -0.01031
C8    2    0.922449   -0.162631    0.754585    11.00000    0.02938    0.03810 =
         0.06603    0.01413    0.02239    0.00243
AFIX  43
H8    3    0.961517   -0.310943    0.794855    11.00000   -1.20000
AFIX   0
C9    2    0.872754   -0.142844    0.617636    11.00000    0.02587    0.04524 =
         0.05476   -0.01798    0.02416   -0.00664
AFIX  43
H9    3    0.877585   -0.278197    0.563746    11.00000   -1.20000
AFIX   0
C10   2    0.816701    0.075436    0.561870    11.00000    0.03727    0.06222 =
         0.02795    0.00205    0.01943   -0.00855
AFIX  43
H10   3    0.783275    0.089552    0.469117    11.00000   -1.20000
AFIX   0
C11   2    0.808365    0.276642    0.640088    11.00000    0.02592    0.03908 =
         0.05066    0.01468    0.02105    0.00620
AFIX  43
H11   3    0.769353    0.425443    0.600487    11.00000   -1.20000
AFIX   0
C12   2    0.856780    0.257268    0.773806    11.00000    0.03026    0.04181 =
         0.03990   -0.01043    0.02554   -0.01074
AFIX  43
H12   3    0.851511    0.392679    0.827409    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0109_bn1 in P2(1)/c
REM wR2 = 0.2379, GooF = S = 1.142, Restrained GooF = 1.163 for all data
REM R1 = 0.0765 for 2017 Fo > 4sig(Fo) and 0.0966 for all 2814 data
REM 138 parameters refined using 102 restraints

END

WGHT      0.1339      0.1141

REM Highest difference peak  0.451,  deepest hole -0.372,  1-sigma level  0.074
Q1    1   0.4056  0.2483  0.5919  11.00000  0.05    0.39
Q2    1   0.3311  0.3339  0.7184  11.00000  0.05    0.33
Q3    1   0.9418 -0.2398  0.7278  11.00000  0.05    0.29
Q4    1   0.3113  0.1346  0.7196  11.00000  0.05    0.28
Q5    1   0.8117  0.2105  0.6996  11.00000  0.05    0.27
Q6    1   0.3689 -0.0134  0.6900  11.00000  0.05    0.27
Q7    1   0.7938  0.1762  0.5878  11.00000  0.05    0.27
Q8    1   0.4523  0.0707  0.6494  11.00000  0.05    0.26
Q9    1   0.9367  0.1668  1.0025  11.00000  0.05    0.26
Q10   1   0.9499 -0.0296  0.9297  11.00000  0.05    0.25
Q11   1   0.3749  0.3827  0.6457  11.00000  0.05    0.24
Q12   1   0.3214  0.1055  0.5408  11.00000  0.05    0.23
Q13   1   0.4945  0.2742  0.6269  11.00000  0.05    0.23
Q14   1   0.5126  0.1806  0.6792  11.00000  0.05    0.23
Q15   1   0.3617  0.1014  0.7980  11.00000  0.05    0.22
Q16   1   0.4014  0.2950  0.4508  11.00000  0.05    0.21
Q17   1   0.8419 -0.0593  0.5655  11.00000  0.05    0.21
Q18   1   0.5000  0.0000  0.5000  10.50000  0.05    0.21
Q19   1   1.0071  0.0364  0.8527  11.00000  0.05    0.21
Q20   1   0.8685 -0.1418  0.6805  11.00000  0.05    0.20
;
_shelx_res_checksum              50153
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_1p9GPa
_database_code_depnum_ccdc_archive 'CCDC 2336590'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_1p9GPa          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.350 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT911_AZO_1p9GPa          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        645 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3r (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-15
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   14.455(9)
_cell_length_b                   5.4916(2)
_cell_length_c                   11.591(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.41(5)
_cell_angle_gamma                90
_cell_volume                     850.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       1909000
_cell_measurement_reflns_used    497
_cell_measurement_theta_min      2.1900
_cell_measurement_theta_max      20.6330

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.66623
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         1909000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    0.50    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.0304349931
_diffrn_orient_matrix_UB_12      0.0062909746
_diffrn_orient_matrix_UB_13      0.0178745702
_diffrn_orient_matrix_UB_21      -0.0035451251
_diffrn_orient_matrix_UB_22      0.0199373149
_diffrn_orient_matrix_UB_23      0.0321485951
_diffrn_orient_matrix_UB_31      0.0016774555
_diffrn_orient_matrix_UB_32      -0.0716744013
_diffrn_orient_matrix_UB_33      0.0105118571
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            3995
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.313
_diffrn_reflns_theta_max         21.167
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.211
_diffrn_measured_fraction_theta_full 0.350
_diffrn_reflns_Laue_measured_fraction_max 0.211
_diffrn_reflns_Laue_measured_fraction_full 0.350
_diffrn_reflns_point_group_measured_fraction_max 0.211
_diffrn_reflns_point_group_measured_fraction_full 0.350
_reflns_number_total             3995
_reflns_number_gt                3372
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
The BASF parameter was refined to 35.6%. The anisotropic displacement 
parameters of the disordered nitrogen atoms N2A and N2B were restrained to 
similar behaviour using SIMU restraint. The anisotropic displacement 
parameters of all atoms were restrained to isotropic behqaviour using ISOR 
restraint.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1065P)²+0.0453P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3995
_refine_ls_number_parameters     138
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1660
_refine_ls_wR_factor_gt          0.1582
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.060
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4893(3) 0.1087(3) 0.5055(2) 0.0247(10) Uani 1 1 d . U . . .
C1 C 0.4315(3) 0.1405(3) 0.5795(2) 0.0211(10) Uani 1 1 d . U . . .
C2 C 0.3811(3) 0.3610(3) 0.5664(2) 0.0251(11) Uani 1 1 d . U . . .
H2 H 0.386163 0.477853 0.511062 0.030 Uiso 1 1 calc R U . . .
C3 C 0.3234(3) 0.4063(3) 0.6356(3) 0.0266(11) Uani 1 1 d . U . . .
H3 H 0.287915 0.551488 0.624787 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3183(3) 0.2347(3) 0.7214(3) 0.0275(12) Uani 1 1 d . U . . .
H4 H 0.279873 0.265471 0.768484 0.033 Uiso 1 1 calc R U . . .
C5 C 0.3708(3) 0.0174(3) 0.7365(2) 0.0262(12) Uani 1 1 d . U . . .
H5 H 0.368700 -0.095164 0.795380 0.031 Uiso 1 1 calc R U . . .
C6 C 0.4263(3) -0.0336(3) 0.6648(2) 0.0219(10) Uani 1 1 d . U . . .
H6 H 0.459681 -0.181436 0.673384 0.026 Uiso 1 1 calc R U . . .
N2A N 0.9673(4) 0.0771(3) 0.9761(4) 0.0307(13) Uani 0.946(10) 1 d . U P A 1
N2B N 0.995(7) -0.097(7) 0.958(7) 0.033(4) Uani 0.054(10) 1 d . U P A 2
C7 C 0.9183(3) 0.0543(4) 0.8446(3) 0.0279(13) Uani 1 1 d . U . . .
C8 C 0.9280(4) -0.1439(4) 0.7740(3) 0.0315(13) Uani 1 1 d . U . . .
H8 H 0.968706 -0.275204 0.812547 0.038 Uiso 1 1 calc R U . . .
C9 C 0.8763(4) -0.1415(4) 0.6463(3) 0.0354(15) Uani 1 1 d . U . . .
H9 H 0.882397 -0.272493 0.598790 0.043 Uiso 1 1 calc R U . . .
C10 C 0.8156(4) 0.0532(4) 0.5879(3) 0.0326(15) Uani 1 1 d . U . . .
H10 H 0.780770 0.052464 0.501853 0.039 Uiso 1 1 calc R U . . .
C11 C 0.8071(4) 0.2497(4) 0.6589(3) 0.0361(15) Uani 1 1 d . U . . .
H11 H 0.767756 0.382716 0.620012 0.043 Uiso 1 1 calc R U . . .
C12 C 0.8565(4) 0.2481(4) 0.7855(3) 0.0322(14) Uani 1 1 d . U . . .
H12 H 0.848651 0.377689 0.832646 0.039 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.027(3) 0.0253(8) 0.0240(12) 0.0000(5) 0.0127(19) 0.0025(8)
C1 0.021(3) 0.0227(8) 0.0194(13) -0.0011(6) 0.008(2) 0.0007(8)
C2 0.026(4) 0.0241(8) 0.0245(15) 0.0018(6) 0.009(2) 0.0041(9)
C3 0.022(4) 0.0263(9) 0.0319(16) -0.0026(7) 0.011(2) 0.0039(9)
C4 0.024(4) 0.0329(10) 0.0279(16) -0.0042(7) 0.013(2) 0.0000(10)
C5 0.025(4) 0.0308(9) 0.0235(15) 0.0008(7) 0.011(2) -0.0008(10)
C6 0.020(3) 0.0235(8) 0.0214(14) 0.0002(6) 0.007(2) 0.0010(8)
N2A 0.029(4) 0.0367(10) 0.025(2) 0.0017(8) 0.009(3) 0.0062(11)
N2B 0.030(7) 0.038(6) 0.026(6) 0.000(6) 0.007(7) 0.006(6)
C7 0.022(4) 0.0359(10) 0.0257(17) 0.0039(7) 0.009(3) 0.0012(11)
C8 0.026(4) 0.0331(10) 0.0353(19) 0.0015(8) 0.011(3) 0.0017(11)
C9 0.032(5) 0.0397(11) 0.037(2) -0.0078(9) 0.016(3) -0.0043(13)
C10 0.022(5) 0.0504(13) 0.0210(18) 0.0010(9) 0.003(3) -0.0042(14)
C11 0.033(5) 0.0395(12) 0.036(2) 0.0098(9) 0.013(3) 0.0076(13)
C12 0.032(5) 0.0356(11) 0.0300(18) 0.0014(8) 0.012(3) 0.0037(11)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.252(3) 3_656 ?
N1 C1 1.418(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.398(2) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2A N2A 1.232(8) 3_757 ?
N2A C7 1.420(5) . ?
N2B N2B 1.41(11) 3_757 ?
N2B C7 1.60(8) . ?
C7 C12 1.390(5) . ?
C7 C8 1.401(3) . ?
C8 C9 1.381(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.391(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 113.8(2) 3_656 . ?
C2 C1 C6 120.4(2) . . ?
C2 C1 N1 116.49(15) . . ?
C6 C1 N1 123.1(2) . . ?
C3 C2 C1 120.02(16) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C6 C5 C4 120.79(17) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N2A N2A C7 113.9(3) 3_757 . ?
N2B N2B C7 91(6) 3_757 . ?
C12 C7 C8 119.7(3) . . ?
C12 C7 N2A 115.2(2) . . ?
C8 C7 N2A 125.1(3) . . ?
C12 C7 N2B 157.0(19) . . ?
C8 C7 N2B 83.3(18) . . ?
C9 C8 C7 119.0(3) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 121.0(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C11 119.5(3) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C7 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -161.9(4) 3_656 . . . ?
N1 N1 C1 C6 20.0(6) 3_656 . . . ?
C6 C1 C2 C3 -1.7(5) . . . . ?
N1 C1 C2 C3 -179.8(3) . . . . ?
C1 C2 C3 C4 2.1(6) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
C3 C4 C5 C6 -1.6(6) . . . . ?
C4 C5 C6 C1 2.0(6) . . . . ?
C2 C1 C6 C5 -0.4(6) . . . . ?
N1 C1 C6 C5 177.6(3) . . . . ?
N2A N2A C7 C12 -169.6(4) 3_757 . . . ?
N2A N2A C7 C8 10.5(7) 3_757 . . . ?
N2B N2B C7 C12 -5(12) 3_757 . . . ?
N2B N2B C7 C8 174(6) 3_757 . . . ?
C12 C7 C8 C9 0.5(5) . . . . ?
N2A C7 C8 C9 -179.6(4) . . . . ?
N2B C7 C8 C9 -179(3) . . . . ?
C7 C8 C9 C10 0.1(6) . . . . ?
C8 C9 C10 C11 0.4(6) . . . . ?
C9 C10 C11 C12 -1.5(6) . . . . ?
C10 C11 C12 C7 2.2(6) . . . . ?
C8 C7 C12 C11 -1.6(5) . . . . ?
N2A C7 C12 C11 178.4(3) . . . . ?
N2B C7 C12 C11 177(6) . . . . ?


_shelx_res_file                  
;
TITL sample_0029_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 15:03:50 on 24-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  14.454545   5.491574  11.591150  90.0000 112.4085  90.0000
ZERR    4.00   0.009165   0.000223   0.002827   0.0000   0.0515   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
OMIT -2 -1 0
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.03
FMAP 2
PLAN 20
WGHT    0.106500    0.045300
BASF   0.35617
FVAR      23.28996   0.94564
N1    1    0.489265    0.108740    0.505462    11.00000    0.02737    0.02527 =
         0.02395   -0.00004    0.01269    0.00255
C1    2    0.431488    0.140518    0.579496    11.00000    0.02103    0.02266 =
         0.01941   -0.00107    0.00764    0.00071
C2    2    0.381055    0.360965    0.566391    11.00000    0.02616    0.02413 =
         0.02447    0.00176    0.00906    0.00405
AFIX  43
H2    3    0.386163    0.477853    0.511062    11.00000   -1.20000
AFIX   0
C3    2    0.323360    0.406309    0.635577    11.00000    0.02246    0.02627 =
         0.03191   -0.00255    0.01118    0.00386
AFIX  43
H3    3    0.287915    0.551488    0.624787    11.00000   -1.20000
AFIX   0
C4    2    0.318276    0.234723    0.721432    11.00000    0.02449    0.03287 =
         0.02793   -0.00420    0.01299   -0.00002
AFIX  43
H4    3    0.279873    0.265471    0.768484    11.00000   -1.20000
AFIX   0
C5    2    0.370813    0.017425    0.736500    11.00000    0.02546    0.03081 =
         0.02355    0.00080    0.01081   -0.00079
AFIX  43
H5    3    0.368700   -0.095164    0.795380    11.00000   -1.20000
AFIX   0
C6    2    0.426342   -0.033581    0.664828    11.00000    0.02025    0.02347 =
         0.02138    0.00020    0.00730    0.00095
AFIX  43
H6    3    0.459681   -0.181436    0.673384    11.00000   -1.20000
AFIX   0
SIMU 0.003 N2A N2B
PART 1 21.
N2A   1    0.967302    0.077097    0.976118    21.00000    0.02911    0.03667 =
         0.02532    0.00171    0.00921    0.00619
PART 2 -21.
N2B   1    0.995469   -0.097098    0.958124   -21.00000    0.03011    0.03827 =
         0.02625   -0.00041    0.00740    0.00639
PART 0
C7    2    0.918267    0.054282    0.844635    11.00000    0.02212    0.03594 =
         0.02570    0.00393    0.00932    0.00117
C8    2    0.928019   -0.143936    0.773985    11.00000    0.02602    0.03308 =
         0.03525    0.00152    0.01149    0.00175
AFIX  43
H8    3    0.968706   -0.275204    0.812547    11.00000   -1.20000
AFIX   0
C9    2    0.876343   -0.141510    0.646289    11.00000    0.03210    0.03967 =
         0.03703   -0.00777    0.01594   -0.00427
AFIX  43
H9    3    0.882397   -0.272493    0.598790    11.00000   -1.20000
AFIX   0
C10   2    0.815605    0.053183    0.587872    11.00000    0.02187    0.05036 =
         0.02098    0.00095    0.00307   -0.00416
AFIX  43
H10   3    0.780770    0.052464    0.501853    11.00000   -1.20000
AFIX   0
C11   2    0.807137    0.249725    0.658887    11.00000    0.03308    0.03949 =
         0.03582    0.00976    0.01337    0.00763
AFIX  43
H11   3    0.767756    0.382716    0.620012    11.00000   -1.20000
AFIX   0
C12   2    0.856467    0.248055    0.785527    11.00000    0.03169    0.03561 =
         0.02998    0.00140    0.01248    0.00373
AFIX  43
H12   3    0.848651    0.377689    0.832646    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0029_bn1 in P2(1)/c
REM wR2 = 0.1660, GooF = S = 1.059, Restrained GooF = 1.046 for all data
REM R1 = 0.0559 for 3372 Fo > 4sig(Fo) and 0.0644 for all 3995 data
REM 138 parameters refined using 96 restraints

END

WGHT      0.1065      0.0453

REM Highest difference peak  0.384,  deepest hole -0.235,  1-sigma level  0.060
Q1    1   0.3984 -0.0085  0.7010  11.00000  0.05    0.38
Q2    1   0.4269  0.0541  0.6210  11.00000  0.05    0.29
Q3    1   0.3551  0.3995  0.6049  11.00000  0.05    0.27
Q4    1   0.9197 -0.0562  0.8201  11.00000  0.05    0.25
Q5    1   0.4541  0.1208  0.5398  11.00000  0.05    0.24
Q6    1   0.3316  0.3176  0.6790  11.00000  0.05    0.23
Q7    1   0.7901  0.1314  0.6109  11.00000  0.05    0.22
Q8    1   0.9420 -0.1272  0.7287  11.00000  0.05    0.20
Q9    1   0.8419  0.2471  0.7304  11.00000  0.05    0.20
Q10   1   0.2818 -0.0255  0.7522  11.00000  0.05    0.19
Q11   1   0.3693  0.1388  0.7543  11.00000  0.05    0.19
Q12   1   0.9177  0.3878  0.8409  11.00000  0.05    0.18
Q13   1   0.7301  0.5251  0.6940  11.00000  0.05    0.18
Q14   1   0.8967 -0.1987  0.7120  11.00000  0.05    0.18
Q15   1   0.4516  0.2738  0.6163  11.00000  0.05    0.18
Q16   1   0.7991  0.5213  0.8324  11.00000  0.05    0.17
Q17   1   1.0713 -0.3103  0.9330  11.00000  0.05    0.17
Q18   1   0.3753  0.2326  0.5525  11.00000  0.05    0.17
Q19   1   0.3177  0.0865  0.7138  11.00000  0.05    0.17
Q20   1   0.8647  0.1101  0.5287  11.00000  0.05    0.16
;
_shelx_res_checksum              29831
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_10GPa
_database_code_depnum_ccdc_archive 'CCDC 2336567'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_10GPa           
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.347 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT411_AZO_10GPa           
;
PROBLEM: Short Inter H...H Contact  H2       ..H11      .       1.95 Ang.  
RESPONSE: Intermolecular distances are strongly shortened at high 
pressure and atoms approach closer to one another than at ambient 
conditions or low temperature.
;
_vrf_PLAT911_AZO_10GPa           
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        554 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3r (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-16
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   13.319(9)
_cell_length_b                   5.1800(2)
_cell_length_c                   10.928(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.91(5)
_cell_angle_gamma                90
_cell_volume                     694.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       10070000
_cell_measurement_reflns_used    535
_cell_measurement_theta_min      2.3310
_cell_measurement_theta_max      20.2800

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.74517
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         10070000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    0.50    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0333132090
_diffrn_orient_matrix_UB_12      0.0069956430
_diffrn_orient_matrix_UB_13      -0.0184115163
_diffrn_orient_matrix_UB_21      0.0030386032
_diffrn_orient_matrix_UB_22      0.0216431163
_diffrn_orient_matrix_UB_23      -0.0344248022
_diffrn_orient_matrix_UB_31      -0.0021623850
_diffrn_orient_matrix_UB_32      -0.0756900637
_diffrn_orient_matrix_UB_33      -0.0115196708
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            3233
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.151
_diffrn_reflns_theta_max         21.711
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.197
_diffrn_measured_fraction_theta_full 0.347
_diffrn_reflns_Laue_measured_fraction_max 0.197
_diffrn_reflns_Laue_measured_fraction_full 0.347
_diffrn_reflns_point_group_measured_fraction_max 0.197
_diffrn_reflns_point_group_measured_fraction_full 0.347
_reflns_number_total             3233
_reflns_number_gt                2778
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
The BASF parameter was refined to 34.6%. The anisotropic displacement parameters 
of the disordered nitrogen atoms N2A and N2B were restrained to 
similar behaviour using SIMU restraint.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1043P)²+0.2224P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3233
_refine_ls_number_parameters     138
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0644
_refine_ls_wR_factor_ref         0.1822
_refine_ls_wR_factor_gt          0.1757
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.066
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4898(4) 0.1158(4) 0.5068(3) 0.0205(15) Uani 1 1 d . . . . .
C1 C 0.4284(5) 0.1472(4) 0.5848(3) 0.0195(17) Uani 1 1 d . . . . .
C2 C 0.3777(5) 0.3821(4) 0.5771(3) 0.0203(17) Uani 1 1 d . . . . .
H2 H 0.383009 0.509152 0.519817 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3193(5) 0.4277(5) 0.6547(4) 0.0208(17) Uani 1 1 d . . . . .
H3 H 0.280776 0.581147 0.645179 0.025 Uiso 1 1 calc R U . . .
C4 C 0.3177(5) 0.2464(5) 0.7469(4) 0.0212(17) Uani 1 1 d . . . . .
H4 H 0.280470 0.280331 0.801521 0.025 Uiso 1 1 calc R U . . .
C5 C 0.3719(5) 0.0143(5) 0.7573(3) 0.0199(17) Uani 1 1 d . . . . .
H5 H 0.372903 -0.105912 0.820986 0.024 Uiso 1 1 calc R U . . .
C6 C 0.4243(5) -0.0393(4) 0.6738(3) 0.0186(15) Uani 1 1 d . . . . .
H6 H 0.456823 -0.199505 0.676974 0.022 Uiso 1 1 calc R U . . .
N2A N 0.9638(9) 0.0788(6) 0.9748(8) 0.029(3) Uani 0.800(18) 1 d . U P A 1
N2B N 0.987(3) -0.097(3) 0.957(3) 0.029(3) Uani 0.200(18) 1 d . U P A 2
C7 C 0.9149(6) 0.0446(6) 0.8339(4) 0.029(2) Uani 1 1 d . . . . .
C8 C 0.9251(6) -0.1638(6) 0.7619(5) 0.034(2) Uani 1 1 d . . . . .
H8 H 0.965201 -0.307770 0.804491 0.041 Uiso 1 1 calc R U . . .
C9 C 0.8750(7) -0.1556(6) 0.6254(5) 0.036(2) Uani 1 1 d . . . . .
H9 H 0.881160 -0.295036 0.575188 0.044 Uiso 1 1 calc R U . . .
C10 C 0.8159(7) 0.0576(7) 0.5633(5) 0.033(3) Uani 1 1 d . . . . .
H10 H 0.782093 0.062727 0.471092 0.039 Uiso 1 1 calc R U . . .
C11 C 0.8068(6) 0.2635(6) 0.6377(5) 0.034(2) Uani 1 1 d . . . . .
H11 H 0.767260 0.408754 0.595836 0.041 Uiso 1 1 calc R U . . .
C12 C 0.8555(6) 0.2548(6) 0.7723(4) 0.031(2) Uani 1 1 d . . . . .
H12 H 0.848240 0.393064 0.822561 0.037 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.025(5) 0.0195(10) 0.0209(17) -0.0010(7) 0.014(3) 0.0005(11)
C1 0.025(5) 0.0179(11) 0.020(2) -0.0012(8) 0.013(3) -0.0002(13)
C2 0.024(6) 0.0185(11) 0.021(2) 0.0011(9) 0.012(3) 0.0009(13)
C3 0.021(5) 0.0196(11) 0.025(2) -0.0011(9) 0.012(3) 0.0024(13)
C4 0.021(5) 0.0238(12) 0.022(2) -0.0018(9) 0.013(3) 0.0001(14)
C5 0.021(6) 0.0217(11) 0.019(2) 0.0010(9) 0.009(3) -0.0005(13)
C6 0.020(5) 0.0178(10) 0.0207(19) -0.0002(8) 0.010(3) 0.0000(12)
N2A 0.039(8) 0.0291(15) 0.025(4) 0.0006(15) 0.019(6) 0.003(2)
N2B 0.039(10) 0.034(5) 0.023(5) 0.000(4) 0.019(8) 0.001(5)
C7 0.020(7) 0.0445(17) 0.020(3) 0.0046(12) 0.006(4) -0.008(2)
C8 0.029(7) 0.0280(15) 0.051(3) 0.0074(13) 0.021(5) 0.0029(18)
C9 0.032(7) 0.0375(17) 0.050(3) -0.0161(15) 0.026(5) -0.008(2)
C10 0.021(8) 0.057(2) 0.020(3) 0.0007(14) 0.008(5) -0.009(2)
C11 0.029(7) 0.0340(16) 0.044(3) 0.0136(14) 0.020(4) 0.0058(19)
C12 0.034(7) 0.0314(15) 0.038(3) -0.0058(12) 0.024(4) -0.0062(17)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.252(4) 3_656 ?
N1 C1 1.402(4) . ?
C1 C2 1.378(4) . ?
C1 C6 1.386(3) . ?
C2 C3 1.376(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2A N2A 1.219(17) 3_757 ?
N2A C7 1.430(9) . ?
N2B N2B 1.32(5) 3_757 ?
N2B C7 1.51(3) . ?
C7 C12 1.360(7) . ?
C7 C8 1.374(5) . ?
C8 C9 1.377(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.373(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.358(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 112.9(3) 3_656 . ?
C2 C1 C6 120.4(3) . . ?
C2 C1 N1 116.9(2) . . ?
C6 C1 N1 122.4(3) . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
N2A N2A C7 110.6(5) 3_757 . ?
N2B N2B C7 99(2) 3_757 . ?
C12 C7 C8 120.9(4) . . ?
C12 C7 N2A 111.5(3) . . ?
C8 C7 N2A 127.5(5) . . ?
C12 C7 N2B 151.5(8) . . ?
C8 C7 N2B 87.6(8) . . ?
C7 C8 C9 118.8(5) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 119.8(4) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 120.0(5) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -163.3(6) 3_656 . . . ?
N1 N1 C1 C6 21.5(8) 3_656 . . . ?
C6 C1 C2 C3 -2.5(8) . . . . ?
N1 C1 C2 C3 -177.8(5) . . . . ?
C1 C2 C3 C4 4.6(8) . . . . ?
C2 C3 C4 C5 -2.4(8) . . . . ?
C3 C4 C5 C6 -2.0(8) . . . . ?
C4 C5 C6 C1 4.1(8) . . . . ?
C2 C1 C6 C5 -1.8(8) . . . . ?
N1 C1 C6 C5 173.2(5) . . . . ?
N2A N2A C7 C12 -163.7(8) 3_757 . . . ?
N2A N2A C7 C8 14.3(13) 3_757 . . . ?
N2B N2B C7 C12 -13(5) 3_757 . . . ?
N2B N2B C7 C8 165(3) 3_757 . . . ?
C12 C7 C8 C9 0.6(9) . . . . ?
N2A C7 C8 C9 -177.2(6) . . . . ?
N2B C7 C8 C9 -178.2(13) . . . . ?
C7 C8 C9 C10 0.0(9) . . . . ?
C8 C9 C10 C11 0.0(9) . . . . ?
C9 C10 C11 C12 -0.5(9) . . . . ?
C10 C11 C12 C7 1.1(9) . . . . ?
C8 C7 C12 C11 -1.2(9) . . . . ?
N2A C7 C12 C11 177.0(6) . . . . ?
N2B C7 C12 C11 176(3) . . . . ?


_shelx_res_file                  
;
TITL sample_0093_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 22:49:48 on 24-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  13.319431   5.179993  10.927610  90.0000 112.9146  90.0000
ZERR    4.00   0.009229   0.000248   0.002729   0.0000   0.0549   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
REM ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.104300    0.222400
BASF   0.34628
FVAR      25.09342   0.79986
N1    1    0.489781    0.115798    0.506822    11.00000    0.02545    0.01951 =
         0.02092   -0.00102    0.01381    0.00046
C1    2    0.428352    0.147214    0.584822    11.00000    0.02519    0.01792 =
         0.01980   -0.00117    0.01341   -0.00024
C2    2    0.377739    0.382081    0.577146    11.00000    0.02447    0.01846 =
         0.02067    0.00107    0.01167    0.00091
AFIX  43
H2    3    0.383009    0.509152    0.519817    11.00000   -1.20000
AFIX   0
C3    2    0.319347    0.427695    0.654737    11.00000    0.02079    0.01957 =
         0.02458   -0.00112    0.01153    0.00238
AFIX  43
H3    3    0.280776    0.581147    0.645179    11.00000   -1.20000
AFIX   0
C4    2    0.317746    0.246428    0.746870    11.00000    0.02147    0.02383 =
         0.02220   -0.00184    0.01272    0.00009
AFIX  43
H4    3    0.280470    0.280331    0.801521    11.00000   -1.20000
AFIX   0
C5    2    0.371921    0.014270    0.757304    11.00000    0.02054    0.02174 =
         0.01884    0.00096    0.00920   -0.00055
AFIX  43
H5    3    0.372903   -0.105912    0.820986    11.00000   -1.20000
AFIX   0
C6    2    0.424340   -0.039347    0.673774    11.00000    0.01952    0.01779 =
         0.02072   -0.00021    0.01037   -0.00002
AFIX  43
H6    3    0.456823   -0.199505    0.676974    11.00000   -1.20000
AFIX   0
SIMU 0.003 N2A N2B
PART 1 21.
N2A   1    0.963780    0.078784    0.974770    21.00000    0.03851    0.02910 =
         0.02460    0.00062    0.01911    0.00302
PART 2 -21.
N2B   1    0.987326   -0.097415    0.957433   -21.00000    0.03857    0.03375 =
         0.02259    0.00020    0.01948    0.00071
PART 0
C7    2    0.914870    0.044591    0.833913    11.00000    0.02027    0.04455 =
         0.01998    0.00463    0.00618   -0.00779
C8    2    0.925110   -0.163763    0.761861    11.00000    0.02929    0.02802 =
         0.05072    0.00743    0.02096    0.00286
AFIX  43
H8    3    0.965201   -0.307770    0.804491    11.00000   -1.20000
AFIX   0
C9    2    0.874970   -0.155614    0.625419    11.00000    0.03153    0.03751 =
         0.04994   -0.01614    0.02627   -0.00805
AFIX  43
H9    3    0.881160   -0.295036    0.575188    11.00000   -1.20000
AFIX   0
C10   2    0.815880    0.057572    0.563272    11.00000    0.02117    0.05675 =
         0.02044    0.00073    0.00848   -0.00947
AFIX  43
H10   3    0.782093    0.062727    0.471092    11.00000   -1.20000
AFIX   0
C11   2    0.806782    0.263513    0.637703    11.00000    0.02909    0.03404 =
         0.04435    0.01357    0.02010    0.00581
AFIX  43
H11   3    0.767260    0.408754    0.595836    11.00000   -1.20000
AFIX   0
C12   2    0.855496    0.254822    0.772317    11.00000    0.03406    0.03140 =
         0.03756   -0.00579    0.02433   -0.00624
AFIX  43
H12   3    0.848240    0.393064    0.822561    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0093_bn1 in P2(1)/c
REM wR2 = 0.1822, GooF = S = 1.066, Restrained GooF = 1.065 for all data
REM R1 = 0.0644 for 2778 Fo > 4sig(Fo) and 0.0721 for all 3233 data
REM 138 parameters refined using 6 restraints

END

WGHT      0.1043      0.2224

REM Highest difference peak  0.568,  deepest hole -0.366,  1-sigma level  0.066
Q1    1   0.9315 -0.0389  0.8073  11.00000  0.05    0.57
Q2    1   0.9090 -0.2152  0.7108  11.00000  0.05    0.39
Q3    1   0.4312  0.0660  0.6300  11.00000  0.05    0.35
Q4    1   0.3394  0.1306  0.7506  11.00000  0.05    0.35
Q5    1   0.4169  0.2622  0.5896  11.00000  0.05    0.35
Q6    1   0.3039  0.3197  0.6785  11.00000  0.05    0.31
Q7    1   0.3428  0.3524  0.7176  11.00000  0.05    0.30
Q8    1   0.8169  0.2346  0.7029  11.00000  0.05    0.30
Q9    1   0.7960  0.1496  0.5927  11.00000  0.05    0.29
Q10   1   0.3760 -0.0044  0.7014  11.00000  0.05    0.25
Q11   1   0.5000  0.0000  0.5000  10.50000  0.05    0.24
Q12   1   0.5211  0.2056  0.4867  11.00000  0.05    0.22
Q13   1   0.9104  0.2256  0.8485  11.00000  0.05    0.22
Q14   1   0.3574  0.3829  0.6321  11.00000  0.05    0.21
Q15   1   0.8621 -0.0948  0.5757  11.00000  0.05    0.20
Q16   1   0.9354  0.1764  0.9942  11.00000  0.05    0.19
Q17   1   0.2864  0.3493  0.5624  11.00000  0.05    0.18
Q18   1   0.4068  0.4527  0.7633  11.00000  0.05    0.18
Q19   1   0.4475  0.1839  0.5312  11.00000  0.05    0.18
Q20   1   0.5002  0.1765  0.6684  11.00000  0.05    0.17
;
_shelx_res_checksum              16298
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_14p1GPa
_database_code_depnum_ccdc_archive 'CCDC 2336576'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_14p1GPa         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.331 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT411_AZO_14p1GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.78 Ang.  
RESPONSE: Intermolecular distances are strongly shortened at high 
pressure and atoms approach closer to one another than at ambient 
conditions or low temperature.
;
_vrf_PLAT149_AZO_14p1GPa         
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.15 Degree
RESPONSE: Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree.
;
_vrf_PLAT911_AZO_14p1GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        591 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3s (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-16
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   12.32(2)
_cell_length_b                   5.4498(7)
_cell_length_c                   10.697(8)
_cell_angle_alpha                90
_cell_angle_beta                 114.60(15)
_cell_angle_gamma                90
_cell_volume                     653.0(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       14120000
_cell_measurement_reflns_used    488
_cell_measurement_theta_min      2.4500
_cell_measurement_theta_max      19.1420

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.853
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.08919
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         14120000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    1.00    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0363683000
_diffrn_orient_matrix_UB_12      0.0062923000
_diffrn_orient_matrix_UB_13      -0.0197932000
_diffrn_orient_matrix_UB_21      0.0029961000
_diffrn_orient_matrix_UB_22      0.0219680000
_diffrn_orient_matrix_UB_23      -0.0351549000
_diffrn_orient_matrix_UB_31      -0.0022032000
_diffrn_orient_matrix_UB_32      -0.0716740000
_diffrn_orient_matrix_UB_33      -0.0123809000
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2541
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.397
_diffrn_reflns_theta_max         21.395
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.194
_diffrn_measured_fraction_theta_full 0.331
_diffrn_reflns_Laue_measured_fraction_max 0.194
_diffrn_reflns_Laue_measured_fraction_full 0.331
_diffrn_reflns_point_group_measured_fraction_max 0.194
_diffrn_reflns_point_group_measured_fraction_full 0.331
_reflns_number_total             2541
_reflns_number_gt                1843
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
 Datasets from multiple crystals were merged in shelXL and their reflections 
 were scaled using HKLF 5 with BASF. The BASF parameter was refined to 51.7%. 
 Some reflections were removed from refinement as outliers. 
 The Uii displacement parameters of all atoms were restrained with ISOR 
 keyword to approximate isotropic behavior.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1813P)²] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2541
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0810
_refine_ls_wR_factor_ref         0.2453
_refine_ls_wR_factor_gt          0.2295
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.074
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4900(7) 0.1113(5) 0.5074(5) 0.0275(19) Uani 1 1 d . U . . .
C1 C 0.4248(7) 0.1426(6) 0.5861(6) 0.027(2) Uani 1 1 d . U . . .
C2 C 0.3803(8) 0.3746(6) 0.5880(6) 0.025(2) Uani 1 1 d . U . . .
H2 H 0.386970 0.498381 0.531769 0.030 Uiso 1 1 calc R U . . .
C3 C 0.3258(8) 0.4180(6) 0.6754(6) 0.028(2) Uani 1 1 d . U . . .
H3 H 0.293283 0.571610 0.676396 0.033 Uiso 1 1 calc R U . . .
C4 C 0.3191(7) 0.2358(6) 0.7614(6) 0.026(2) Uani 1 1 d . U . . .
H4 H 0.282537 0.268361 0.820087 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3657(8) 0.0071(6) 0.7614(6) 0.027(2) Uani 1 1 d . U . . .
H5 H 0.363497 -0.112976 0.822097 0.032 Uiso 1 1 calc R U . . .
C6 C 0.4156(7) -0.0427(6) 0.6707(5) 0.026(2) Uani 1 1 d . U . . .
H6 H 0.443184 -0.199671 0.665832 0.031 Uiso 1 1 calc R U . . .
N2 N 0.9867(7) 0.1076(5) 0.9794(5) 0.028(2) Uani 1 1 d . U . . .
C7 C 0.9220(8) 0.1232(6) 0.8360(6) 0.026(2) Uani 1 1 d . U . . .
C8 C 0.9125(8) -0.0704(6) 0.7463(6) 0.028(2) Uani 1 1 d . U . . .
H8 H 0.940340 -0.225705 0.780855 0.033 Uiso 1 1 calc R U . . .
C9 C 0.8621(8) -0.0301(6) 0.6075(6) 0.029(2) Uani 1 1 d . U . . .
H9 H 0.858440 -0.155928 0.547101 0.035 Uiso 1 1 calc R U . . .
C10 C 0.8172(8) 0.1974(7) 0.5582(6) 0.029(2) Uani 1 1 d . U . . .
H10 H 0.780590 0.223687 0.463734 0.035 Uiso 1 1 calc R U . . .
C11 C 0.8255(8) 0.3875(6) 0.6465(6) 0.028(2) Uani 1 1 d . U . . .
H11 H 0.795709 0.541367 0.611209 0.034 Uiso 1 1 calc R U . . .
C12 C 0.8775(8) 0.3517(6) 0.7866(6) 0.027(2) Uani 1 1 d . U . . .
H12 H 0.882354 0.479268 0.846473 0.033 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.035(6) 0.0313(16) 0.023(3) -0.0003(11) 0.018(4) 0.0009(16)
C1 0.034(7) 0.0301(16) 0.022(3) 0.0004(12) 0.018(4) 0.0014(18)
C2 0.027(7) 0.0305(16) 0.020(3) -0.0006(13) 0.012(4) -0.0004(18)
C3 0.033(7) 0.0295(16) 0.025(3) -0.0003(13) 0.017(4) 0.0009(18)
C4 0.026(7) 0.0339(17) 0.023(3) -0.0002(14) 0.015(4) 0.0011(19)
C5 0.029(7) 0.0303(17) 0.025(3) 0.0009(14) 0.015(4) 0.0011(19)
C6 0.028(6) 0.0303(16) 0.023(3) 0.0002(13) 0.015(4) 0.0005(18)
N2 0.033(6) 0.0322(16) 0.024(3) 0.0024(12) 0.017(4) 0.0018(17)
C7 0.026(7) 0.0342(17) 0.018(3) 0.0002(13) 0.010(4) -0.0024(19)
C8 0.032(7) 0.0293(15) 0.026(3) -0.0003(13) 0.017(4) -0.0026(18)
C9 0.032(7) 0.0335(17) 0.026(3) -0.0018(14) 0.018(4) -0.003(2)
C10 0.030(7) 0.0371(17) 0.023(3) 0.0011(16) 0.014(4) -0.001(2)
C11 0.032(7) 0.0322(17) 0.023(3) 0.0026(14) 0.014(4) 0.0016(19)
C12 0.030(7) 0.0327(17) 0.024(3) 0.0018(14) 0.016(4) 0.0016(19)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.261(6) 3_656 ?
N1 C1 1.396(6) . ?
C1 C2 1.381(6) . ?
C1 C6 1.391(5) . ?
C2 C3 1.380(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.248(7) 3_757 ?
N2 C7 1.406(9) . ?
C7 C12 1.374(7) . ?
C7 C8 1.398(5) . ?
C8 C9 1.368(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(8) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 112.7(4) 3_656 . ?
C2 C1 C6 121.0(4) . . ?
C2 C1 N1 116.9(3) . . ?
C6 C1 N1 121.7(4) . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C4 C3 C2 120.6(4) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 120.9(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.2(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 119.8(4) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N2 N2 C7 112.9(5) 3_757 . ?
C12 C7 C8 120.9(5) . . ?
C12 C7 N2 115.4(4) . . ?
C8 C7 N2 123.4(5) . . ?
C9 C8 C7 119.6(4) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 119.4(4) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C9 C10 C11 120.9(5) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 120.6(4) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C7 C12 C11 118.5(4) . . ?
C7 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -168.9(9) 3_656 . . . ?
N1 N1 C1 C6 18.0(13) 3_656 . . . ?
C6 C1 C2 C3 -0.4(12) . . . . ?
N1 C1 C2 C3 -173.6(7) . . . . ?
C1 C2 C3 C4 1.8(12) . . . . ?
C2 C3 C4 C5 -0.4(12) . . . . ?
C3 C4 C5 C6 -2.4(12) . . . . ?
C4 C5 C6 C1 3.8(12) . . . . ?
C2 C1 C6 C5 -2.5(13) . . . . ?
N1 C1 C6 C5 170.4(7) . . . . ?
N2 N2 C7 C12 172.2(7) 3_757 . . . ?
N2 N2 C7 C8 -14.1(12) 3_757 . . . ?
C12 C7 C8 C9 2.4(12) . . . . ?
N2 C7 C8 C9 -170.9(7) . . . . ?
C7 C8 C9 C10 -2.7(11) . . . . ?
C8 C9 C10 C11 2.1(11) . . . . ?
C9 C10 C11 C12 -1.1(11) . . . . ?
C8 C7 C12 C11 -1.4(12) . . . . ?
N2 C7 C12 C11 172.4(7) . . . . ?
C10 C11 C12 C7 0.7(12) . . . . ?


_shelx_res_file                  
;
TITL sample_0125_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 10:29:59 on 27-Feb-2023
REM P2(1)/c (#14 in standard setting)
CELL 0.41000  12.319681   5.449772  10.696946  90.0000 114.5963  90.0000
ZERR    4.00   0.021964   0.000748   0.007660   0.0000   0.1519   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
OMIT -4 5 5
OMIT -10 4 14
OMIT 6 0 -10
OMIT 1 8 -5
OMIT -8 5 15
OMIT -6 5 12
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.181300
BASF   0.51742
FVAR      30.02022
N1    1    0.490021    0.111290    0.507413    11.00000    0.03457    0.03128 =
         0.02251   -0.00027    0.01773    0.00087
C1    2    0.424758    0.142644    0.586122    11.00000    0.03420    0.03009 =
         0.02218    0.00042    0.01785    0.00142
C2    2    0.380325    0.374561    0.588005    11.00000    0.02664    0.03050 =
         0.01985   -0.00058    0.01152   -0.00039
AFIX  43
H2    3    0.386970    0.498381    0.531769    11.00000   -1.20000
AFIX   0
C3    2    0.325807    0.417999    0.675434    11.00000    0.03326    0.02945 =
         0.02496   -0.00034    0.01720    0.00092
AFIX  43
H3    3    0.293283    0.571610    0.676396    11.00000   -1.20000
AFIX   0
C4    2    0.319113    0.235801    0.761354    11.00000    0.02578    0.03388 =
         0.02307   -0.00020    0.01460    0.00109
AFIX  43
H4    3    0.282537    0.268361    0.820087    11.00000   -1.20000
AFIX   0
C5    2    0.365681    0.007066    0.761393    11.00000    0.02939    0.03026 =
         0.02479    0.00087    0.01501    0.00112
AFIX  43
H5    3    0.363497   -0.112976    0.822097    11.00000   -1.20000
AFIX   0
C6    2    0.415613   -0.042653    0.670662    11.00000    0.02797    0.03029 =
         0.02270    0.00019    0.01468    0.00048
AFIX  43
H6    3    0.443184   -0.199671    0.665832    11.00000   -1.20000
AFIX   0
N2    1    0.986684    0.107574    0.979374    11.00000    0.03304    0.03219 =
         0.02395    0.00244    0.01659    0.00179
C7    2    0.921967    0.123230    0.835997    11.00000    0.02584    0.03421 =
         0.01832    0.00024    0.01047   -0.00239
C8    2    0.912531   -0.070389    0.746329    11.00000    0.03227    0.02926 =
         0.02600   -0.00033    0.01697   -0.00264
AFIX  43
H8    3    0.940340   -0.225705    0.780855    11.00000   -1.20000
AFIX   0
C9    2    0.862148   -0.030092    0.607475    11.00000    0.03243    0.03355 =
         0.02608   -0.00178    0.01750   -0.00316
AFIX  43
H9    3    0.858440   -0.155928    0.547101    11.00000   -1.20000
AFIX   0
C10   2    0.817194    0.197370    0.558155    11.00000    0.02972    0.03707 =
         0.02311    0.00112    0.01424   -0.00058
AFIX  43
H10   3    0.780590    0.223687    0.463734    11.00000   -1.20000
AFIX   0
C11   2    0.825481    0.387502    0.646498    11.00000    0.03231    0.03223 =
         0.02253    0.00256    0.01391    0.00164
AFIX  43
H11   3    0.795709    0.541367    0.611209    11.00000   -1.20000
AFIX   0
C12   2    0.877462    0.351716    0.786599    11.00000    0.02969    0.03274 =
         0.02405    0.00181    0.01562    0.00155
AFIX  43
H12   3    0.882354    0.479268    0.846473    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0125_bn1 in P2(1)/c
REM wR2 = 0.2453, GooF = S = 1.025, Restrained GooF = 1.017 for all data
REM R1 = 0.0810 for 1843 Fo > 4sig(Fo) and 0.0994 for all 2541 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.1813      0.0000

REM Highest difference peak  0.421,  deepest hole -0.304,  1-sigma level  0.074
Q1    1   0.4209  0.2573  0.5934  11.00000  0.05    0.42
Q2    1   0.3357  0.1169  0.7609  11.00000  0.05    0.39
Q3    1   0.9388  0.2599  0.8357  11.00000  0.05    0.36
Q4    1   0.7884  0.0537  0.5429  11.00000  0.05    0.33
Q5    1   0.4873  0.2511  0.4904  11.00000  0.05    0.29
Q6    1   1.0000  0.0000  1.0000  10.50000  0.05    0.28
Q7    1   0.5000  0.0000  0.5000  10.50000  0.05    0.28
Q8    1   0.3074  0.3027  0.6920  11.00000  0.05    0.27
Q9    1   0.3421  0.3559  0.7482  11.00000  0.05    0.27
Q10   1   1.0666  0.1821  1.0576  11.00000  0.05    0.25
Q11   1   0.3953  0.0403  0.6094  11.00000  0.05    0.25
Q12   1   0.3632  0.5843  0.4871  11.00000  0.05    0.24
Q13   1   0.8468  0.3094  0.6121  11.00000  0.05    0.23
Q14   1   0.9668  0.0242  0.8136  11.00000  0.05    0.22
Q15   1   1.1173  0.1320  1.0566  11.00000  0.05    0.22
Q16   1   0.3793  0.1285  0.4470  11.00000  0.05    0.21
Q17   1   0.9457  0.1672  0.6372  11.00000  0.05    0.21
Q18   1   0.2085  0.4525  0.6087  11.00000  0.05    0.20
Q19   1   0.4214 -0.1713  0.9583  11.00000  0.05    0.20
Q20   1   0.3930 -0.0804  0.7282  11.00000  0.05    0.20
;
_shelx_res_checksum              33371
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_14p9GPa
_database_code_depnum_ccdc_archive 'CCDC 2336578'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_14p9GPa         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.346 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT411_AZO_14p9GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.74 Ang.  
RESPONSE: Intermolecular distances are strongly shortened at high 
pressure and atoms approach closer to one another than at ambient 
conditions or low temperature.
;
_vrf_PLAT149_AZO_14p9GPa         
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.11 Degree
RESPONSE:  Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree.
;
_vrf_PLAT911_AZO_14p9GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        572 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3s (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-16
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   12.230(15)
_cell_length_b                   5.4789(4)
_cell_length_c                   10.620(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.88(11)
_cell_angle_gamma                90
_cell_volume                     645.5(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       14930000
_cell_measurement_reflns_used    532
_cell_measurement_theta_min      2.2080
_cell_measurement_theta_max      20.6280

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.875
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.09403
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         14930000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    1.00    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0368263892
_diffrn_orient_matrix_UB_12      0.0067589414
_diffrn_orient_matrix_UB_13      -0.0202544413
_diffrn_orient_matrix_UB_21      0.0031516249
_diffrn_orient_matrix_UB_22      0.0221284374
_diffrn_orient_matrix_UB_23      -0.0351808596
_diffrn_orient_matrix_UB_31      -0.0024420006
_diffrn_orient_matrix_UB_32      -0.0710656485
_diffrn_orient_matrix_UB_33      -0.0127601665
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2764
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.213
_diffrn_reflns_theta_max         21.420
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.207
_diffrn_measured_fraction_theta_full 0.346
_diffrn_reflns_Laue_measured_fraction_max 0.207
_diffrn_reflns_Laue_measured_fraction_full 0.346
_diffrn_reflns_point_group_measured_fraction_max 0.207
_diffrn_reflns_point_group_measured_fraction_full 0.346
_reflns_number_total             2764
_reflns_number_gt                2213
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
 Datasets from multiple crystals were merged in shelXL and their reflections 
 were scaled using HKLF 5 with BASF. The BASF parameter was refined to 24.9%. 
 The Uii displacement parameters of all atoms were restrained with ISOR 
 keyword to approximate isotropic behavior.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1906P)²] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2764
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0847
_refine_ls_wR_factor_ref         0.2566
_refine_ls_wR_factor_gt          0.2452
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.077
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4906(6) 0.1105(4) 0.5080(4) 0.0230(18) Uani 1 1 d . U . . .
C1 C 0.4235(7) 0.1417(5) 0.5856(5) 0.023(2) Uani 1 1 d . U . . .
C2 C 0.3809(7) 0.3737(5) 0.5893(5) 0.022(2) Uani 1 1 d . U . . .
H2 H 0.389306 0.498038 0.534397 0.026 Uiso 1 1 calc R U . . .
C3 C 0.3253(7) 0.4159(6) 0.6768(5) 0.024(2) Uani 1 1 d . U . . .
H3 H 0.291847 0.568100 0.677605 0.029 Uiso 1 1 calc R U . . .
C4 C 0.3192(7) 0.2339(6) 0.7627(5) 0.024(2) Uani 1 1 d . U . . .
H4 H 0.284146 0.266299 0.823515 0.029 Uiso 1 1 calc R U . . .
C5 C 0.3637(7) 0.0059(5) 0.7602(5) 0.023(2) Uani 1 1 d . U . . .
H5 H 0.359779 -0.114898 0.819665 0.028 Uiso 1 1 calc R U . . .
C6 C 0.4142(7) -0.0440(5) 0.6698(5) 0.0218(19) Uani 1 1 d . U . . .
H6 H 0.441903 -0.200226 0.664798 0.026 Uiso 1 1 calc R U . . .
N2 N 0.9880(6) 0.1077(4) 0.9795(4) 0.0259(19) Uani 1 1 d . U . . .
C7 C 0.9220(7) 0.1269(6) 0.8359(5) 0.023(2) Uani 1 1 d . U . . .
C8 C 0.9116(7) -0.0652(6) 0.7454(5) 0.022(2) Uani 1 1 d . U . . .
H8 H 0.939582 -0.220048 0.779821 0.026 Uiso 1 1 calc R U . . .
C9 C 0.8598(7) -0.0229(6) 0.6052(5) 0.024(2) Uani 1 1 d . U . . .
H9 H 0.853724 -0.148235 0.543609 0.028 Uiso 1 1 calc R U . . .
C10 C 0.8167(7) 0.2059(6) 0.5563(5) 0.026(2) Uani 1 1 d . U . . .
H10 H 0.779874 0.233740 0.461136 0.031 Uiso 1 1 calc R U . . .
C11 C 0.8276(8) 0.3943(6) 0.6465(5) 0.025(2) Uani 1 1 d . U . . .
H11 H 0.799472 0.548854 0.611648 0.031 Uiso 1 1 calc R U . . .
C12 C 0.8795(7) 0.3563(5) 0.7874(5) 0.023(2) Uani 1 1 d . U . . .
H12 H 0.885747 0.482673 0.848493 0.028 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.028(6) 0.0283(14) 0.016(2) 0.0002(10) 0.012(4) 0.0016(15)
C1 0.029(6) 0.0264(14) 0.017(3) -0.0004(11) 0.013(4) 0.0007(17)
C2 0.024(6) 0.0266(14) 0.015(3) -0.0006(11) 0.009(4) -0.0012(17)
C3 0.029(7) 0.0268(14) 0.020(3) -0.0003(12) 0.014(4) 0.0017(17)
C4 0.027(6) 0.0302(15) 0.019(3) -0.0010(12) 0.013(4) 0.0000(18)
C5 0.025(6) 0.0275(15) 0.018(3) 0.0018(12) 0.010(4) 0.0011(17)
C6 0.023(6) 0.0259(14) 0.019(3) -0.0008(12) 0.011(4) -0.0005(17)
N2 0.034(6) 0.0286(14) 0.020(3) 0.0019(11) 0.016(4) 0.0014(15)
C7 0.026(6) 0.0295(15) 0.017(3) 0.0012(12) 0.012(4) -0.0003(17)
C8 0.023(6) 0.0265(14) 0.019(3) 0.0001(12) 0.010(4) -0.0014(17)
C9 0.023(7) 0.0297(15) 0.018(3) -0.0016(12) 0.009(4) -0.0023(18)
C10 0.029(7) 0.0320(15) 0.018(3) 0.0022(14) 0.011(4) 0.001(2)
C11 0.031(7) 0.0286(15) 0.019(3) 0.0035(12) 0.013(4) 0.0033(18)
C12 0.028(6) 0.0278(14) 0.017(3) 0.0014(12) 0.012(4) 0.0011(18)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.257(5) 3_656 ?
N1 C1 1.396(6) . ?
C1 C2 1.381(5) . ?
C1 C6 1.391(4) . ?
C2 C3 1.384(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.249(6) 3_757 ?
N2 C7 1.398(8) . ?
C7 C12 1.375(6) . ?
C7 C8 1.394(5) . ?
C8 C9 1.371(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.374(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 112.5(4) 3_656 . ?
C2 C1 C6 121.4(3) . . ?
C2 C1 N1 116.9(3) . . ?
C6 C1 N1 121.2(4) . . ?
C1 C2 C3 118.2(3) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N2 N2 C7 113.2(5) 3_757 . ?
C12 C7 C8 121.4(5) . . ?
C12 C7 N2 115.6(3) . . ?
C8 C7 N2 122.6(4) . . ?
C9 C8 C7 119.1(4) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 120.8(4) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 120.6(4) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 118.4(3) . . ?
C11 C12 H12 120.8 . . ?
C7 C12 H12 120.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -169.4(8) 3_656 . . . ?
N1 N1 C1 C6 19.0(11) 3_656 . . . ?
C6 C1 C2 C3 -1.7(11) . . . . ?
N1 C1 C2 C3 -173.3(6) . . . . ?
C1 C2 C3 C4 3.5(11) . . . . ?
C2 C3 C4 C5 -2.3(11) . . . . ?
C3 C4 C5 C6 -0.7(11) . . . . ?
C4 C5 C6 C1 2.5(11) . . . . ?
C2 C1 C6 C5 -1.3(12) . . . . ?
N1 C1 C6 C5 169.9(6) . . . . ?
N2 N2 C7 C12 171.7(7) 3_757 . . . ?
N2 N2 C7 C8 -15.7(11) 3_757 . . . ?
C12 C7 C8 C9 1.1(11) . . . . ?
N2 C7 C8 C9 -171.0(6) . . . . ?
C7 C8 C9 C10 -1.3(10) . . . . ?
C8 C9 C10 C11 1.5(10) . . . . ?
C9 C10 C11 C12 -1.3(11) . . . . ?
C10 C11 C12 C7 1.0(11) . . . . ?
C8 C7 C12 C11 -0.9(11) . . . . ?
N2 C7 C12 C11 171.7(6) . . . . ?


_shelx_res_file                  
;
TITL sample_0133_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 10:35:29 on 27-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  12.229551   5.478913  10.620071  90.0000 114.8816  90.0000
ZERR    4.00   0.015312   0.000427   0.005523   0.0000   0.1084   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.190600
BASF   0.24947
FVAR      26.52620
N1    1    0.490625    0.110525    0.507991    11.00000    0.02762    0.02832 =
         0.01632    0.00019    0.01237    0.00161
C1    2    0.423545    0.141721    0.585553    11.00000    0.02942    0.02644 =
         0.01696   -0.00040    0.01338    0.00072
C2    2    0.380883    0.373658    0.589253    11.00000    0.02406    0.02655 =
         0.01475   -0.00064    0.00899   -0.00120
AFIX  43
H2    3    0.389306    0.498038    0.534397    11.00000   -1.20000
AFIX   0
C3    2    0.325251    0.415927    0.676831    11.00000    0.02948    0.02684 =
         0.01989   -0.00026    0.01351    0.00175
AFIX  43
H3    3    0.291847    0.568100    0.677605    11.00000   -1.20000
AFIX   0
C4    2    0.319160    0.233895    0.762690    11.00000    0.02676    0.03023 =
         0.01852   -0.00102    0.01302    0.00004
AFIX  43
H4    3    0.284146    0.266299    0.823515    11.00000   -1.20000
AFIX   0
C5    2    0.363733    0.005869    0.760183    11.00000    0.02488    0.02750 =
         0.01774    0.00184    0.01022    0.00110
AFIX  43
H5    3    0.359779   -0.114898    0.819665    11.00000   -1.20000
AFIX   0
C6    2    0.414208   -0.044044    0.669795    11.00000    0.02329    0.02591 =
         0.01856   -0.00080    0.01103   -0.00048
AFIX  43
H6    3    0.441903   -0.200226    0.664798    11.00000   -1.20000
AFIX   0
N2    1    0.988010    0.107652    0.979534    11.00000    0.03408    0.02863 =
         0.01997    0.00185    0.01636    0.00142
C7    2    0.921975    0.126912    0.835880    11.00000    0.02593    0.02945 =
         0.01693    0.00124    0.01182   -0.00025
C8    2    0.911639   -0.065196    0.745446    11.00000    0.02271    0.02652 =
         0.01857    0.00008    0.01026   -0.00139
AFIX  43
H8    3    0.939582   -0.220048    0.779821    11.00000   -1.20000
AFIX   0
C9    2    0.859768   -0.022885    0.605246    11.00000    0.02304    0.02966 =
         0.01840   -0.00162    0.00899   -0.00227
AFIX  43
H9    3    0.853724   -0.148235    0.543609    11.00000   -1.20000
AFIX   0
C10   2    0.816749    0.205909    0.556323    11.00000    0.02893    0.03203 =
         0.01816    0.00222    0.01117    0.00091
AFIX  43
H10   3    0.779874    0.233740    0.461136    11.00000   -1.20000
AFIX   0
C11   2    0.827573    0.394300    0.646457    11.00000    0.03115    0.02856 =
         0.01890    0.00347    0.01260    0.00330
AFIX  43
H11   3    0.799472    0.548854    0.611648    11.00000   -1.20000
AFIX   0
C12   2    0.879491    0.356281    0.787375    11.00000    0.02794    0.02777 =
         0.01700    0.00142    0.01163    0.00113
AFIX  43
H12   3    0.885747    0.482673    0.848493    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0133_bn1 in P2(1)/c
REM wR2 = 0.2566, GooF = S = 1.116, Restrained GooF = 1.108 for all data
REM R1 = 0.0847 for 2213 Fo > 4sig(Fo) and 0.0946 for all 2764 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.1906      0.0000

REM Highest difference peak  0.497,  deepest hole -0.280,  1-sigma level  0.077
Q1    1   0.8156  0.0744  0.5563  11.00000  0.05    0.50
Q2    1   0.8880  0.2242  0.7980  11.00000  0.05    0.34
Q3    1   0.9503  0.0344  0.7991  11.00000  0.05    0.34
Q4    1   0.4359  0.2656  0.6234  11.00000  0.05    0.34
Q5    1   0.3333  0.2324  0.5125  11.00000  0.05    0.32
Q6    1   0.3224  0.0951  0.7419  11.00000  0.05    0.32
Q7    1   0.3805  0.0622  0.6195  11.00000  0.05    0.32
Q8    1   0.8048  0.2780  0.6046  11.00000  0.05    0.30
Q9    1   0.3785  0.0049  0.7036  11.00000  0.05    0.29
Q10   1   0.3764  0.1241  0.7849  11.00000  0.05    0.28
Q11   1   0.3588  0.3176  0.7320  11.00000  0.05    0.28
Q12   1   0.2710  0.3398  0.7011  11.00000  0.05    0.26
Q13   1   0.4767  0.0414  0.6525  11.00000  0.05    0.26
Q14   1   0.9567  0.2630  0.8526  11.00000  0.05    0.25
Q15   1   0.8674 -0.1022  0.8935  11.00000  0.05    0.24
Q16   1   0.6999  0.0628  0.4472  11.00000  0.05    0.24
Q17   1   0.4271 -0.0543  0.7453  11.00000  0.05    0.24
Q18   1   0.7283  0.3254  0.5708  11.00000  0.05    0.22
Q19   1   1.0448  0.2136  1.0383  11.00000  0.05    0.22
Q20   1   0.9114  0.5732  0.8654  11.00000  0.05    0.22
;
_shelx_res_checksum              57284
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_18p5GPa
_database_code_depnum_ccdc_archive 'CCDC 2336585'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_18p5GPa         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.359 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT411_AZO_18p5GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.68 Ang.  
RESPONSE: Intermolecular distances are strongly shortened at high 
pressure and atoms approach closer to one another than at ambient 
conditions or low temperature.
;
_vrf_PLAT149_AZO_18p5GPa         
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.09 Degree
RESPONSE: Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree.
;
_vrf_PLAT911_AZO_18p5GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        527 Report
RESPONSE:  Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3s (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-16
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   11.918(13)
_cell_length_b                   5.5121(3)
_cell_length_c                   10.502(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.90(9)
_cell_angle_gamma                90
_cell_volume                     620.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       18510000
_cell_measurement_reflns_used    480
_cell_measurement_theta_min      2.2350
_cell_measurement_theta_max      20.5790

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.950
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.32594
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         18510000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    1.00    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0381573973
_diffrn_orient_matrix_UB_12      0.0064910780
_diffrn_orient_matrix_UB_13      -0.0212288040
_diffrn_orient_matrix_UB_21      0.0031402926
_diffrn_orient_matrix_UB_22      0.0224365640
_diffrn_orient_matrix_UB_23      -0.0354665694
_diffrn_orient_matrix_UB_31      -0.0023503576
_diffrn_orient_matrix_UB_32      -0.0705092762
_diffrn_orient_matrix_UB_33      -0.0131282484
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2903
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0110
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.237
_diffrn_reflns_theta_max         21.502
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.209
_diffrn_measured_fraction_theta_full 0.359
_diffrn_reflns_Laue_measured_fraction_max 0.209
_diffrn_reflns_Laue_measured_fraction_full 0.359
_diffrn_reflns_point_group_measured_fraction_max 0.209
_diffrn_reflns_point_group_measured_fraction_full 0.359
_reflns_number_total             2903
_reflns_number_gt                2484
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
 Datasets from multiple crystals were merged in shelXL and their reflections 
 were scaled using HKLF 5 with BASF. The BASF parameter was refined to 22.6%. 
 Some reflections were removed from refinement as outliers. 
 The Uii displacement parameters of all atoms were restrained with ISOR 
 keyword to approximate isotropic behavior.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1271P)²+0.0267P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2903
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1788
_refine_ls_wR_factor_gt          0.1731
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.068
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4909(4) 0.1104(3) 0.5085(3) 0.0169(14) Uani 1 1 d . U . . .
C1 C 0.4222(5) 0.1418(4) 0.5858(4) 0.0181(15) Uani 1 1 d . U . . .
C2 C 0.3804(5) 0.3732(4) 0.5915(4) 0.0167(16) Uani 1 1 d . U . . .
H2 H 0.389057 0.497687 0.536679 0.020 Uiso 1 1 calc R U . . .
C3 C 0.3254(5) 0.4142(4) 0.6811(4) 0.0189(15) Uani 1 1 d . U . . .
H3 H 0.293766 0.566974 0.684775 0.023 Uiso 1 1 calc R U . . .
C4 C 0.3171(5) 0.2308(4) 0.7648(4) 0.0183(16) Uani 1 1 d . U . . .
H4 H 0.280838 0.261648 0.825561 0.022 Uiso 1 1 calc R U . . .
C5 C 0.3615(5) 0.0019(4) 0.7607(4) 0.0178(16) Uani 1 1 d . U . . .
H5 H 0.358385 -0.119257 0.820690 0.021 Uiso 1 1 calc R U . . .
C6 C 0.4101(5) -0.0448(4) 0.6673(4) 0.0168(15) Uani 1 1 d . U . . .
H6 H 0.435075 -0.201235 0.658307 0.020 Uiso 1 1 calc R U . . .
N2 N 0.9907(4) 0.1092(3) 0.9808(3) 0.0177(14) Uani 1 1 d . U . . .
C7 C 0.9222(5) 0.1344(4) 0.8354(4) 0.0171(15) Uani 1 1 d . U . . .
C8 C 0.9074(5) -0.0556(4) 0.7423(4) 0.0183(16) Uani 1 1 d . U . . .
H8 H 0.932696 -0.211661 0.776421 0.022 Uiso 1 1 calc R U . . .
C9 C 0.8551(5) -0.0104(4) 0.5997(4) 0.0179(16) Uani 1 1 d . U . . .
H9 H 0.845049 -0.134733 0.535773 0.022 Uiso 1 1 calc R U . . .
C10 C 0.8179(5) 0.2213(4) 0.5530(4) 0.0200(16) Uani 1 1 d . U . . .
H10 H 0.782373 0.253162 0.456403 0.024 Uiso 1 1 calc R U . . .
C11 C 0.8319(6) 0.4073(4) 0.6456(4) 0.0179(15) Uani 1 1 d . U . . .
H11 H 0.806383 0.563031 0.611069 0.021 Uiso 1 1 calc R U . . .
C12 C 0.8830(5) 0.3657(4) 0.7883(4) 0.0194(16) Uani 1 1 d . U . . .
H12 H 0.891010 0.490235 0.851448 0.023 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.018(4) 0.0186(9) 0.0119(18) -0.0003(7) 0.005(3) 0.0019(10)
C1 0.024(5) 0.0174(9) 0.0138(19) -0.0005(8) 0.009(3) 0.0002(11)
C2 0.017(5) 0.0178(9) 0.012(2) 0.0001(8) 0.003(3) 0.0003(12)
C3 0.024(5) 0.0170(9) 0.015(2) 0.0001(8) 0.008(3) 0.0014(12)
C4 0.020(5) 0.0199(9) 0.015(2) 0.0002(8) 0.007(3) 0.0011(12)
C5 0.018(5) 0.0187(10) 0.014(2) 0.0012(8) 0.004(3) 0.0007(12)
C6 0.017(5) 0.0165(9) 0.0136(19) 0.0000(8) 0.004(3) 0.0001(12)
N2 0.019(4) 0.0191(9) 0.0137(19) 0.0016(7) 0.006(3) 0.0010(10)
C7 0.019(5) 0.0183(9) 0.012(2) 0.0010(8) 0.006(3) 0.0001(12)
C8 0.021(5) 0.0167(9) 0.017(2) 0.0013(8) 0.007(3) 0.0003(12)
C9 0.017(5) 0.0187(10) 0.015(2) -0.0006(8) 0.004(3) -0.0011(12)
C10 0.023(5) 0.0199(9) 0.016(2) 0.0012(9) 0.007(3) -0.0001(13)
C11 0.019(5) 0.0184(9) 0.014(2) 0.0020(8) 0.005(3) 0.0014(12)
C12 0.024(5) 0.0175(9) 0.016(2) 0.0014(8) 0.008(3) 0.0017(12)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.263(3) 3_656 ?
N1 C1 1.393(4) . ?
C1 C2 1.380(4) . ?
C1 C6 1.385(3) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.364(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.258(4) 3_757 ?
N2 C7 1.389(5) . ?
C7 C12 1.374(4) . ?
C7 C8 1.390(3) . ?
C8 C9 1.370(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.370(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.368(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 112.5(3) 3_656 . ?
C2 C1 C6 121.5(2) . . ?
C2 C1 N1 117.1(2) . . ?
C6 C1 N1 120.9(3) . . ?
C1 C2 C3 118.0(2) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 121.3(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 119.03(19) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 119.7(2) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2 N2 C7 112.6(3) 3_757 . ?
C12 C7 N2 115.6(2) . . ?
C12 C7 C8 121.8(3) . . ?
N2 C7 C8 122.1(3) . . ?
C9 C8 C7 119.3(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 118.8(2) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C9 C10 C11 121.5(3) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 117.9(2) . . ?
C11 C12 H12 121.0 . . ?
C7 C12 H12 121.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -170.1(5) 3_656 . . . ?
N1 N1 C1 C6 17.7(8) 3_656 . . . ?
C6 C1 C2 C3 -0.2(8) . . . . ?
N1 C1 C2 C3 -172.3(4) . . . . ?
C1 C2 C3 C4 2.2(8) . . . . ?
C2 C3 C4 C5 -0.9(8) . . . . ?
C3 C4 C5 C6 -2.6(8) . . . . ?
C4 C5 C6 C1 4.6(8) . . . . ?
C2 C1 C6 C5 -3.3(8) . . . . ?
N1 C1 C6 C5 168.6(5) . . . . ?
N2 N2 C7 C12 171.0(5) 3_757 . . . ?
N2 N2 C7 C8 -16.7(7) 3_757 . . . ?
C12 C7 C8 C9 1.6(8) . . . . ?
N2 C7 C8 C9 -170.3(5) . . . . ?
C7 C8 C9 C10 -0.5(7) . . . . ?
C8 C9 C10 C11 0.0(8) . . . . ?
C9 C10 C11 C12 -0.5(8) . . . . ?
C10 C11 C12 C7 1.5(8) . . . . ?
N2 C7 C12 C11 170.3(4) . . . . ?
C8 C7 C12 C11 -2.1(8) . . . . ?


_shelx_res_file                  
;
TITL sample_0152_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 10:47:24 on 27-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  11.918272   5.512133  10.502220  90.0000 115.9029  90.0000
ZERR    4.00   0.012683   0.000322   0.004794   0.0000   0.0948   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
OMIT 1 -4 -10
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.127100    0.026700
BASF   0.22621
FVAR      25.35501
N1    1    0.490944    0.110408    0.508532    11.00000    0.01832    0.01861 =
         0.01192   -0.00025    0.00482    0.00191
C1    2    0.422217    0.141787    0.585821    11.00000    0.02368    0.01739 =
         0.01378   -0.00048    0.00868    0.00015
C2    2    0.380419    0.373206    0.591518    11.00000    0.01717    0.01776 =
         0.01190    0.00011    0.00346    0.00034
AFIX  43
H2    3    0.389057    0.497687    0.536679    11.00000   -1.20000
AFIX   0
C3    2    0.325383    0.414228    0.681143    11.00000    0.02366    0.01705 =
         0.01515    0.00007    0.00771    0.00144
AFIX  43
H3    3    0.293766    0.566974    0.684775    11.00000   -1.20000
AFIX   0
C4    2    0.317149    0.230765    0.764790    11.00000    0.01956    0.01993 =
         0.01473    0.00015    0.00690    0.00113
AFIX  43
H4    3    0.280838    0.261648    0.825561    11.00000   -1.20000
AFIX   0
C5    2    0.361508    0.001865    0.760675    11.00000    0.01756    0.01869 =
         0.01425    0.00119    0.00430    0.00068
AFIX  43
H5    3    0.358385   -0.119257    0.820690    11.00000   -1.20000
AFIX   0
C6    2    0.410146   -0.044814    0.667252    11.00000    0.01727    0.01647 =
         0.01358   -0.00002    0.00380    0.00012
AFIX  43
H6    3    0.435075   -0.201235    0.658307    11.00000   -1.20000
AFIX   0
N2    1    0.990692    0.109213    0.980803    11.00000    0.01855    0.01913 =
         0.01372    0.00155    0.00553    0.00105
C7    2    0.922196    0.134362    0.835374    11.00000    0.01935    0.01829 =
         0.01236    0.00103    0.00575    0.00011
C8    2    0.907391   -0.055607    0.742294    11.00000    0.02054    0.01669 =
         0.01653    0.00129    0.00696    0.00029
AFIX  43
H8    3    0.932696   -0.211661    0.776421    11.00000   -1.20000
AFIX   0
C9    2    0.855112   -0.010397    0.599731    11.00000    0.01694    0.01874 =
         0.01499   -0.00064    0.00411   -0.00109
AFIX  43
H9    3    0.845049   -0.134733    0.535773    11.00000   -1.20000
AFIX   0
C10   2    0.817912    0.221269    0.553048    11.00000    0.02277    0.01991 =
         0.01599    0.00120    0.00724   -0.00013
AFIX  43
H10   3    0.782373    0.253162    0.456403    11.00000   -1.20000
AFIX   0
C11   2    0.831899    0.407277    0.645635    11.00000    0.01872    0.01836 =
         0.01390    0.00198    0.00457    0.00137
AFIX  43
H11   3    0.806383    0.563031    0.611069    11.00000   -1.20000
AFIX   0
C12   2    0.883019    0.365727    0.788287    11.00000    0.02414    0.01752 =
         0.01587    0.00141    0.00809    0.00168
AFIX  43
H12   3    0.891010    0.490235    0.851448    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0152_bn1 in P2(1)/c
REM wR2 = 0.1788, GooF = S = 1.119, Restrained GooF = 1.106 for all data
REM R1 = 0.0606 for 2484 Fo > 4sig(Fo) and 0.0666 for all 2903 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.1271      0.0267

REM Highest difference peak  0.369,  deepest hole -0.241,  1-sigma level  0.068
Q1    1   0.3798 -0.0159  0.7147  11.00000  0.05    0.37
Q2    1   0.3414  0.4113  0.6336  11.00000  0.05    0.35
Q3    1   0.3567  0.3196  0.7327  11.00000  0.05    0.35
Q4    1   0.8897  0.2437  0.7977  11.00000  0.05    0.32
Q5    1   0.8670 -0.0198  0.6649  11.00000  0.05    0.31
Q6    1   0.8558  0.3211  0.6125  11.00000  0.05    0.31
Q7    1   0.4372  0.1537  0.5414  11.00000  0.05    0.28
Q8    1   0.8134  0.0869  0.5530  11.00000  0.05    0.26
Q9    1   0.3966  0.0186  0.5973  11.00000  0.05    0.25
Q10   1   0.9356  0.0489  0.7978  11.00000  0.05    0.24
Q11   1   0.3882  0.2512  0.5687  11.00000  0.05    0.23
Q12   1   0.4479  0.2582  0.6222  11.00000  0.05    0.21
Q13   1   0.4477  0.2223  0.4592  11.00000  0.05    0.20
Q14   1   0.3592  0.1177  0.7716  11.00000  0.05    0.19
Q15   1   0.3861  0.2422  0.8943  11.00000  0.05    0.18
Q16   1   0.3376  0.1989  0.9215  11.00000  0.05    0.18
Q17   1   0.1956  0.4177  0.6772  11.00000  0.05    0.18
Q18   1   0.7950  0.4611  0.6880  11.00000  0.05    0.18
Q19   1   0.4095  0.4551  0.7991  11.00000  0.05    0.18
Q20   1   0.2552  0.1001  0.6787  11.00000  0.05    0.17
;
_shelx_res_checksum              63661
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_19GPa
_database_code_depnum_ccdc_archive 'CCDC 2336586'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_19GPa           
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.358 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT411_AZO_19GPa           
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.67 Ang.  
RESPONSE: Intermolecular distances are strongly shortened at high 
pressure and atoms approach closer to one another than at ambient 
conditions or low temperature.
;
_vrf_PLAT149_AZO_19GPa           
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.09 Degree
RESPONSE: Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree.
;
_vrf_PLAT911_AZO_19GPa           
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        526 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3t (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-21
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   11.882(11)
_cell_length_b                   5.5101(3)
_cell_length_c                   10.490(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.01(9)
_cell_angle_gamma                90
_cell_volume                     617.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       18970000
_cell_measurement_reflns_used    486
_cell_measurement_theta_min      2.2330
_cell_measurement_theta_max      20.4080

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.961
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.35682
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         18970000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    1.00    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0383196210
_diffrn_orient_matrix_UB_12      0.0064072139
_diffrn_orient_matrix_UB_13      -0.0213026868
_diffrn_orient_matrix_UB_21      0.0030961661
_diffrn_orient_matrix_UB_22      0.0225094870
_diffrn_orient_matrix_UB_23      -0.0355161679
_diffrn_orient_matrix_UB_31      -0.0023345229
_diffrn_orient_matrix_UB_32      -0.0705178014
_diffrn_orient_matrix_UB_33      -0.0131673962
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2831
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0108
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.240
_diffrn_reflns_theta_max         21.522
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.209
_diffrn_measured_fraction_theta_full 0.358
_diffrn_reflns_Laue_measured_fraction_max 0.209
_diffrn_reflns_Laue_measured_fraction_full 0.358
_diffrn_reflns_point_group_measured_fraction_max 0.209
_diffrn_reflns_point_group_measured_fraction_full 0.358
_reflns_number_total             2831
_reflns_number_gt                2423
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
 Datasets from multiple crystals were merged in shelXL and their reflections 
 were scaled using HKLF 5 with BASF. The BASF parameter was refined to 20.7%. 
 The Uii displacement parameters of all atoms were restrained with ISOR 
 keyword to approximate isotropic behavior.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1365P)²+0.0220P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2831
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1848
_refine_ls_wR_factor_gt          0.1789
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.077
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4909(5) 0.1104(3) 0.5086(3) 0.0178(16) Uani 1 1 d . U . . .
C1 C 0.4219(5) 0.1418(4) 0.5857(4) 0.0184(17) Uani 1 1 d . U . . .
C2 C 0.3804(5) 0.3732(4) 0.5917(4) 0.0163(18) Uani 1 1 d . U . . .
H2 H 0.389144 0.497814 0.536964 0.020 Uiso 1 1 calc R U . . .
C3 C 0.3253(5) 0.4142(4) 0.6816(4) 0.0186(18) Uani 1 1 d . U . . .
H3 H 0.293579 0.566919 0.685260 0.022 Uiso 1 1 calc R U . . .
C4 C 0.3174(6) 0.2305(4) 0.7652(4) 0.0180(17) Uani 1 1 d . U . . .
H4 H 0.281368 0.261494 0.826391 0.022 Uiso 1 1 calc R U . . .
C5 C 0.3613(5) 0.0015(4) 0.7609(4) 0.0181(18) Uani 1 1 d . U . . .
H5 H 0.357966 -0.119857 0.820720 0.022 Uiso 1 1 calc R U . . .
C6 C 0.4100(5) -0.0450(4) 0.6673(4) 0.0176(17) Uani 1 1 d . U . . .
H6 H 0.435169 -0.201361 0.658319 0.021 Uiso 1 1 calc R U . . .
N2 N 0.9908(5) 0.1094(3) 0.9808(3) 0.0178(16) Uani 1 1 d . U . . .
C7 C 0.9223(5) 0.1350(4) 0.8354(4) 0.0165(17) Uani 1 1 d . U . . .
C8 C 0.9069(5) -0.0550(4) 0.7418(4) 0.0187(18) Uani 1 1 d . U . . .
H8 H 0.931830 -0.211404 0.775904 0.022 Uiso 1 1 calc R U . . .
C9 C 0.8547(5) -0.0097(4) 0.5991(4) 0.0184(19) Uani 1 1 d . U . . .
H9 H 0.844504 -0.133992 0.535013 0.022 Uiso 1 1 calc R U . . .
C10 C 0.8176(6) 0.2224(4) 0.5524(4) 0.0196(18) Uani 1 1 d . U . . .
H10 H 0.781909 0.254482 0.455630 0.024 Uiso 1 1 calc R U . . .
C11 C 0.8320(6) 0.4084(4) 0.6454(4) 0.0180(17) Uani 1 1 d . U . . .
H11 H 0.806715 0.564376 0.610898 0.022 Uiso 1 1 calc R U . . .
C12 C 0.8833(6) 0.3667(4) 0.7883(4) 0.0193(18) Uani 1 1 d . U . . .
H12 H 0.891401 0.491223 0.851583 0.023 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.021(5) 0.0181(9) 0.013(2) -0.0003(7) 0.007(3) 0.0023(11)
C1 0.025(5) 0.0167(9) 0.014(2) 0.0000(8) 0.009(3) 0.0010(12)
C2 0.016(6) 0.0174(10) 0.012(2) 0.0003(8) 0.003(3) 0.0006(12)
C3 0.024(6) 0.0164(9) 0.014(2) -0.0001(8) 0.007(3) 0.0013(12)
C4 0.020(6) 0.0191(10) 0.015(2) 0.0002(8) 0.007(3) 0.0008(13)
C5 0.019(6) 0.0176(10) 0.015(2) 0.0013(9) 0.006(4) 0.0007(13)
C6 0.020(5) 0.0159(9) 0.015(2) -0.0003(8) 0.006(3) 0.0001(12)
N2 0.019(5) 0.0185(10) 0.014(2) 0.0018(7) 0.006(3) 0.0013(11)
C7 0.018(5) 0.0177(10) 0.013(2) 0.0014(8) 0.005(3) 0.0008(12)
C8 0.022(6) 0.0160(9) 0.017(2) 0.0014(8) 0.008(3) 0.0006(12)
C9 0.019(6) 0.0177(10) 0.016(2) -0.0005(8) 0.006(4) -0.0012(13)
C10 0.023(6) 0.0193(10) 0.015(2) 0.0014(9) 0.007(4) 0.0001(13)
C11 0.020(6) 0.0176(10) 0.014(2) 0.0021(8) 0.005(3) 0.0016(12)
C12 0.025(6) 0.0168(10) 0.016(2) 0.0010(8) 0.009(4) 0.0012(12)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.262(3) 3_656 ?
N1 C1 1.393(4) . ?
C1 C2 1.378(4) . ?
C1 C6 1.385(3) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.365(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.260(4) 3_757 ?
N2 C7 1.386(5) . ?
C7 C12 1.374(4) . ?
C7 C8 1.392(3) . ?
C8 C9 1.369(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 112.5(3) 3_656 . ?
C2 C1 C6 121.6(2) . . ?
C2 C1 N1 117.1(2) . . ?
C6 C1 N1 120.8(3) . . ?
C1 C2 C3 118.0(2) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 121.6(2) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 118.9(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 119.7(2) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2 N2 C7 112.6(3) 3_757 . ?
C12 C7 N2 115.7(2) . . ?
C12 C7 C8 121.7(3) . . ?
N2 C7 C8 122.2(3) . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 118.8(2) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C9 C10 C11 121.5(3) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 117.9(2) . . ?
C11 C12 H12 121.0 . . ?
C7 C12 H12 121.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -170.3(6) 3_656 . . . ?
N1 N1 C1 C6 17.9(8) 3_656 . . . ?
C6 C1 C2 C3 -0.4(8) . . . . ?
N1 C1 C2 C3 -172.1(5) . . . . ?
C1 C2 C3 C4 2.4(8) . . . . ?
C2 C3 C4 C5 -1.1(8) . . . . ?
C3 C4 C5 C6 -2.3(8) . . . . ?
C4 C5 C6 C1 4.2(8) . . . . ?
C2 C1 C6 C5 -3.0(8) . . . . ?
N1 C1 C6 C5 168.5(5) . . . . ?
N2 N2 C7 C12 170.9(5) 3_757 . . . ?
N2 N2 C7 C8 -16.5(7) 3_757 . . . ?
C12 C7 C8 C9 1.9(8) . . . . ?
N2 C7 C8 C9 -170.3(5) . . . . ?
C7 C8 C9 C10 -0.8(8) . . . . ?
C8 C9 C10 C11 0.1(8) . . . . ?
C9 C10 C11 C12 -0.5(8) . . . . ?
C10 C11 C12 C7 1.6(8) . . . . ?
N2 C7 C12 C11 170.4(5) . . . . ?
C8 C7 C12 C11 -2.2(8) . . . . ?


_shelx_res_file                  
;
TITL sample_0154_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 17:35:21 on 21-Mar-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  11.882263   5.510119  10.490267  90.0000 116.0081  90.0000
ZERR    4.00   0.011265   0.000286   0.004346   0.0000   0.0853   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
OMIT -2 -1 0
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.03
FMAP 2
PLAN 20
WGHT    0.136500    0.022000
BASF   0.20701
FVAR      25.29330
N1    1    0.490941    0.110437    0.508551    11.00000    0.02127    0.01811 =
         0.01331   -0.00028    0.00680    0.00226
C1    2    0.421869    0.141819    0.585660    11.00000    0.02526    0.01666 =
         0.01401   -0.00002    0.00919    0.00099
C2    2    0.380362    0.373164    0.591701    11.00000    0.01641    0.01739 =
         0.01186    0.00032    0.00318    0.00062
AFIX  43
H2    3    0.389144    0.497814    0.536964    11.00000   -1.20000
AFIX   0
C3    2    0.325322    0.414186    0.681552    11.00000    0.02372    0.01642 =
         0.01401   -0.00013    0.00674    0.00127
AFIX  43
H3    3    0.293579    0.566919    0.685260    11.00000   -1.20000
AFIX   0
C4    2    0.317371    0.230488    0.765211    11.00000    0.01966    0.01910 =
         0.01464    0.00021    0.00699    0.00075
AFIX  43
H4    3    0.281368    0.261494    0.826391    11.00000   -1.20000
AFIX   0
C5    2    0.361338    0.001481    0.760867    11.00000    0.01926    0.01763 =
         0.01534    0.00127    0.00560    0.00070
AFIX  43
H5    3    0.357966   -0.119857    0.820720    11.00000   -1.20000
AFIX   0
C6    2    0.410045   -0.044983    0.667254    11.00000    0.01983    0.01588 =
         0.01495   -0.00029    0.00569    0.00008
AFIX  43
H6    3    0.435169   -0.201361    0.658319    11.00000   -1.20000
AFIX   0
N2    1    0.990793    0.109449    0.980826    11.00000    0.01894    0.01846 =
         0.01430    0.00176    0.00576    0.00128
C7    2    0.922331    0.134999    0.835433    11.00000    0.01771    0.01771 =
         0.01260    0.00137    0.00536    0.00076
C8    2    0.906897   -0.055049    0.741832    11.00000    0.02217    0.01595 =
         0.01713    0.00136    0.00796    0.00058
AFIX  43
H8    3    0.931830   -0.211404    0.775904    11.00000   -1.20000
AFIX   0
C9    2    0.854666   -0.009674    0.599123    11.00000    0.01918    0.01773 =
         0.01636   -0.00049    0.00598   -0.00116
AFIX  43
H9    3    0.844504   -0.133992    0.535013    11.00000   -1.20000
AFIX   0
C10   2    0.817614    0.222360    0.552444    11.00000    0.02262    0.01926 =
         0.01549    0.00141    0.00702    0.00006
AFIX  43
H10   3    0.781909    0.254482    0.455630    11.00000   -1.20000
AFIX   0
C11   2    0.832042    0.408397    0.645437    11.00000    0.01985    0.01761 =
         0.01380    0.00206    0.00485    0.00156
AFIX  43
H11   3    0.806715    0.564376    0.610898    11.00000   -1.20000
AFIX   0
C12   2    0.883256    0.366680    0.788282    11.00000    0.02463    0.01677 =
         0.01613    0.00103    0.00851    0.00120
AFIX  43
H12   3    0.891401    0.491223    0.851583    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0154_bn1 in P2(1)/c
REM wR2 = 0.184772, GooF = S = 1.09721, Restrained GooF = 1.08065 for all data
REM R1 = 0.062754 for 2423 Fo > 4sig(Fo) and 0.068591 for all 2831 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.1363      0.0224

REM Highest difference peak  0.333,  deepest hole -0.338,  1-sigma level  0.077
Q1    1   0.7983  0.3058  0.5959  11.00000  0.05    0.33
Q2    1   0.3593  0.3250  0.7307  11.00000  0.05    0.32
Q3    1   0.3485 -0.0220  0.7042  11.00000  0.05    0.31
Q4    1   0.8674  0.0021  0.6634  11.00000  0.05    0.30
Q5    1   0.8998  0.0476  0.7876  11.00000  0.05    0.29
Q6    1   0.8110  0.0907  0.5561  11.00000  0.05    0.29
Q7    1   0.9510  0.2619  0.8500  11.00000  0.05    0.28
Q8    1   0.2859  0.3071  0.7031  11.00000  0.05    0.27
Q9    1   0.3193  0.4084  0.6239  11.00000  0.05    0.27
Q10   1   0.4584  0.2581  0.6335  11.00000  0.05    0.26
Q11   1   0.3922  0.0261  0.5947  11.00000  0.05    0.26
Q12   1   0.8898  0.2403  0.7980  11.00000  0.05    0.26
Q13   1   1.0000  0.0000  1.0000  10.50000  0.05    0.25
Q14   1   1.0216  0.2048  1.0284  11.00000  0.05    0.25
Q15   1   0.8628  0.3723  0.7271  11.00000  0.05    0.25
Q16   1   0.2900  0.1112  0.7276  11.00000  0.05    0.24
Q17   1   0.4695  0.0960  0.5505  11.00000  0.05    0.24
Q18   1   0.8036  0.4629  0.7000  11.00000  0.05    0.23
Q19   1   0.5474  0.0123  0.5293  11.00000  0.05    0.23
Q20   1   0.9484  0.1273  0.8925  11.00000  0.05    0.21
;
_shelx_res_checksum              39228
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_18GPa
_database_code_depnum_ccdc_archive 'CCDC 2336584'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_18GPa           
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.344 Why?  
RESPONSE:  Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT411_AZO_18GPa           
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.70 Ang.  
RESPONSE: Intermolecular distances are strongly shortened at high 
pressure and atoms approach closer to one another than at ambient 
conditions or low temperature.
;
_vrf_PLAT149_AZO_18GPa           
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.11 Degree
RESPONSE: Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree.
;
_vrf_PLAT911_AZO_18GPa           
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        568 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3s (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-16
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   11.945(14)
_cell_length_b                   5.5180(4)
_cell_length_c                   10.526(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.90(11)
_cell_angle_gamma                90
_cell_volume                     624.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       17980000
_cell_measurement_reflns_used    476
_cell_measurement_theta_min      2.4610
_cell_measurement_theta_max      20.3610

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.939
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51779
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         17980000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    1.00    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0379972000
_diffrn_orient_matrix_UB_12      0.0065217000
_diffrn_orient_matrix_UB_13      -0.0211565000
_diffrn_orient_matrix_UB_21      0.0031597000
_diffrn_orient_matrix_UB_22      0.0223787000
_diffrn_orient_matrix_UB_23      -0.0354180000
_diffrn_orient_matrix_UB_31      -0.0023589000
_diffrn_orient_matrix_UB_32      -0.0705145000
_diffrn_orient_matrix_UB_33      -0.0130836000
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2636
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0114
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.232
_diffrn_reflns_theta_max         21.465
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.205
_diffrn_measured_fraction_theta_full 0.344
_diffrn_reflns_Laue_measured_fraction_max 0.205
_diffrn_reflns_Laue_measured_fraction_full 0.344
_diffrn_reflns_point_group_measured_fraction_max 0.205
_diffrn_reflns_point_group_measured_fraction_full 0.344
_reflns_number_total             2636
_reflns_number_gt                2159
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
 Datasets from multiple crystals were merged in shelXL and their reflections 
 were scaled using HKLF 5 with BASF. The BASF parameter was refined to 21.1%. 
 The Uii displacement parameters of all atoms were restrained with ISOR 
 keyword to approximate isotropic behavior.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1361P)²+0.0192P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2636
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1949
_refine_ls_wR_factor_gt          0.1857
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.072
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4905(5) 0.1104(3) 0.5082(3) 0.0180(16) Uani 1 1 d . U . . .
C1 C 0.4225(6) 0.1417(4) 0.5858(4) 0.0196(17) Uani 1 1 d . U . . .
C2 C 0.3801(6) 0.3730(4) 0.5910(4) 0.0174(18) Uani 1 1 d . U . . .
H2 H 0.387978 0.497133 0.535703 0.021 Uiso 1 1 calc R U . . .
C3 C 0.3259(6) 0.4138(4) 0.6809(4) 0.0191(17) Uani 1 1 d . U . . .
H3 H 0.294715 0.566658 0.684882 0.023 Uiso 1 1 calc R U . . .
C4 C 0.3175(6) 0.2308(4) 0.7646(4) 0.0193(17) Uani 1 1 d . U . . .
H4 H 0.281413 0.262014 0.825300 0.023 Uiso 1 1 calc R U . . .
C5 C 0.3614(6) 0.0021(4) 0.7603(4) 0.0188(18) Uani 1 1 d . U . . .
H5 H 0.357556 -0.119114 0.819680 0.023 Uiso 1 1 calc R U . . .
C6 C 0.4108(6) -0.0447(4) 0.6675(4) 0.0172(17) Uani 1 1 d . U . . .
H6 H 0.436472 -0.200630 0.659337 0.021 Uiso 1 1 calc R U . . .
N2 N 0.9908(5) 0.1091(3) 0.9809(3) 0.0201(17) Uani 1 1 d . U . . .
C7 C 0.9221(6) 0.1338(4) 0.8353(4) 0.0178(17) Uani 1 1 d . U . . .
C8 C 0.9080(6) -0.0563(4) 0.7428(4) 0.0181(17) Uani 1 1 d . U . . .
H8 H 0.933950 -0.211858 0.777043 0.022 Uiso 1 1 calc R U . . .
C9 C 0.8552(6) -0.0114(4) 0.6001(4) 0.0204(19) Uani 1 1 d . U . . .
H9 H 0.845058 -0.135756 0.536333 0.025 Uiso 1 1 calc R U . . .
C10 C 0.8178(6) 0.2199(4) 0.5534(4) 0.0213(18) Uani 1 1 d . U . . .
H10 H 0.782455 0.251641 0.456982 0.026 Uiso 1 1 calc R U . . .
C11 C 0.8313(6) 0.4060(4) 0.6457(4) 0.0195(18) Uani 1 1 d . U . . .
H11 H 0.805358 0.561374 0.611144 0.023 Uiso 1 1 calc R U . . .
C12 C 0.8827(6) 0.3646(4) 0.7882(4) 0.0193(18) Uani 1 1 d . U . . .
H12 H 0.890759 0.489084 0.851177 0.023 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.018(5) 0.0208(10) 0.013(2) -0.0001(8) 0.006(3) 0.0019(12)
C1 0.025(5) 0.0199(10) 0.016(2) 0.0000(9) 0.010(3) 0.0004(14)
C2 0.017(6) 0.0202(10) 0.013(2) -0.0002(9) 0.004(3) -0.0005(14)
C3 0.021(6) 0.0196(10) 0.015(2) -0.0005(9) 0.006(3) 0.0007(14)
C4 0.020(5) 0.0219(10) 0.016(2) 0.0001(9) 0.008(3) 0.0004(15)
C5 0.018(6) 0.0205(11) 0.015(2) 0.0013(9) 0.005(3) 0.0006(14)
C6 0.015(5) 0.0194(10) 0.015(2) -0.0002(9) 0.004(3) -0.0007(14)
N2 0.024(5) 0.0207(11) 0.016(2) 0.0013(8) 0.008(3) 0.0006(12)
C7 0.018(5) 0.0204(10) 0.013(2) 0.0012(9) 0.006(3) 0.0003(14)
C8 0.016(5) 0.0194(10) 0.016(2) 0.0016(9) 0.005(3) 0.0005(14)
C9 0.021(6) 0.0211(11) 0.019(2) -0.0010(9) 0.009(4) -0.0018(15)
C10 0.024(6) 0.0221(11) 0.017(2) 0.0016(10) 0.008(3) -0.0006(15)
C11 0.021(6) 0.0204(10) 0.015(2) 0.0023(9) 0.006(3) 0.0020(14)
C12 0.021(6) 0.0199(11) 0.016(2) 0.0014(9) 0.007(3) 0.0019(14)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.265(4) 3_656 ?
N1 C1 1.392(5) . ?
C1 C2 1.383(4) . ?
C1 C6 1.386(3) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.257(4) 3_757 ?
N2 C7 1.393(6) . ?
C7 C12 1.373(4) . ?
C7 C8 1.391(4) . ?
C8 C9 1.374(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 112.6(3) 3_656 . ?
C2 C1 C6 121.5(3) . . ?
C2 C1 N1 117.1(2) . . ?
C6 C1 N1 121.0(3) . . ?
C3 C2 C1 117.9(2) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 121.3(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 119.1(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2 N2 C7 112.4(4) 3_757 . ?
C12 C7 C8 121.9(4) . . ?
C12 C7 N2 115.6(3) . . ?
C8 C7 N2 122.0(3) . . ?
C9 C8 C7 119.1(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 118.8(3) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C11 121.6(4) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 118.0(2) . . ?
C11 C12 H12 121.0 . . ?
C7 C12 H12 121.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -170.2(6) 3_656 . . . ?
N1 N1 C1 C6 17.3(9) 3_656 . . . ?
C6 C1 C2 C3 0.2(9) . . . . ?
N1 C1 C2 C3 -172.3(5) . . . . ?
C1 C2 C3 C4 1.6(9) . . . . ?
C2 C3 C4 C5 -0.7(9) . . . . ?
C3 C4 C5 C6 -2.0(10) . . . . ?
C4 C5 C6 C1 3.8(9) . . . . ?
C2 C1 C6 C5 -2.9(9) . . . . ?
N1 C1 C6 C5 169.3(5) . . . . ?
N2 N2 C7 C12 170.7(5) 3_757 . . . ?
N2 N2 C7 C8 -17.1(8) 3_757 . . . ?
C12 C7 C8 C9 1.2(9) . . . . ?
N2 C7 C8 C9 -170.4(5) . . . . ?
C7 C8 C9 C10 -0.1(8) . . . . ?
C8 C9 C10 C11 -0.4(9) . . . . ?
C9 C10 C11 C12 -0.2(9) . . . . ?
C10 C11 C12 C7 1.2(9) . . . . ?
C8 C7 C12 C11 -1.7(9) . . . . ?
N2 C7 C12 C11 170.4(5) . . . . ?


_shelx_res_file                  
;
TITL sample_0150_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 10:46:03 on 27-Feb-2023
REM P2(1)/c (#14 in standard setting)
CELL 0.41000  11.944784   5.517959  10.525957  90.0000 115.8998  90.0000
ZERR    4.00   0.014073   0.000361   0.005412   0.0000   0.1057   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.136100    0.019200
BASF   0.21092
FVAR      25.39406
N1    1    0.490512    0.110431    0.508175    11.00000    0.01843    0.02079 =
         0.01347   -0.00009    0.00583    0.00194
C1    2    0.422456    0.141655    0.585826    11.00000    0.02499    0.01990 =
         0.01556    0.00002    0.01032    0.00037
C2    2    0.380112    0.373042    0.591049    11.00000    0.01653    0.02020 =
         0.01284   -0.00016    0.00409   -0.00050
AFIX  43
H2    3    0.387978    0.497133    0.535703    11.00000   -1.20000
AFIX   0
C3    2    0.325872    0.413835    0.680921    11.00000    0.02122    0.01957 =
         0.01493   -0.00050    0.00643    0.00073
AFIX  43
H3    3    0.294715    0.566658    0.684882    11.00000   -1.20000
AFIX   0
C4    2    0.317493    0.230781    0.764561    11.00000    0.01971    0.02195 =
         0.01635    0.00010    0.00804    0.00037
AFIX  43
H4    3    0.281413    0.262014    0.825300    11.00000   -1.20000
AFIX   0
C5    2    0.361392    0.002111    0.760324    11.00000    0.01806    0.02055 =
         0.01496    0.00126    0.00458    0.00061
AFIX  43
H5    3    0.357556   -0.119114    0.819680    11.00000   -1.20000
AFIX   0
C6    2    0.410830   -0.044668    0.667518    11.00000    0.01475    0.01944 =
         0.01487   -0.00025    0.00403   -0.00073
AFIX  43
H6    3    0.436472   -0.200630    0.659337    11.00000   -1.20000
AFIX   0
N2    1    0.990830    0.109056    0.980916    11.00000    0.02351    0.02065 =
         0.01594    0.00133    0.00845    0.00059
C7    2    0.922102    0.133785    0.835340    11.00000    0.01844    0.02036 =
         0.01310    0.00121    0.00562    0.00030
C8    2    0.907994   -0.056341    0.742782    11.00000    0.01613    0.01942 =
         0.01644    0.00156    0.00495    0.00048
AFIX  43
H8    3    0.933950   -0.211858    0.777043    11.00000   -1.20000
AFIX   0
C9    2    0.855223   -0.011419    0.600109    11.00000    0.02138    0.02111 =
         0.01859   -0.00096    0.00854   -0.00183
AFIX  43
H9    3    0.845058   -0.135756    0.536333    11.00000   -1.20000
AFIX   0
C10   2    0.817818    0.219910    0.553418    11.00000    0.02357    0.02215 =
         0.01712    0.00156    0.00801   -0.00060
AFIX  43
H10   3    0.782455    0.251641    0.456982    11.00000   -1.20000
AFIX   0
C11   2    0.831336    0.406031    0.645731    11.00000    0.02076    0.02036 =
         0.01549    0.00232    0.00627    0.00198
AFIX  43
H11   3    0.805358    0.561374    0.611144    11.00000   -1.20000
AFIX   0
C12   2    0.882736    0.364618    0.788193    11.00000    0.02074    0.01987 =
         0.01597    0.00143    0.00667    0.00187
AFIX  43
H12   3    0.890759    0.489084    0.851177    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0150_bn1 in P2(1)/c
REM wR2 = 0.1949, GooF = S = 1.132, Restrained GooF = 1.117 for all data
REM R1 = 0.0628 for 2159 Fo > 4sig(Fo) and 0.0711 for all 2636 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.1361      0.0192

REM Highest difference peak  0.335,  deepest hole -0.254,  1-sigma level  0.072
Q1    1   0.9735  0.0364  0.8075  11.00000  0.05    0.33
Q2    1   0.8904  0.2349  0.7971  11.00000  0.05    0.33
Q3    1   0.3720  0.3145  0.7411  11.00000  0.05    0.32
Q4    1   0.3876  0.0566  0.6203  11.00000  0.05    0.30
Q5    1   0.8295  0.0974  0.5678  11.00000  0.05    0.29
Q6    1   0.8724  0.3093  0.6095  11.00000  0.05    0.29
Q7    1   0.8773  0.0528  0.7852  11.00000  0.05    0.28
Q8    1   0.3729  0.3831  0.6337  11.00000  0.05    0.27
Q9    1   0.7905  0.2965  0.5930  11.00000  0.05    0.27
Q10   1   0.2806  0.3229  0.7033  11.00000  0.05    0.26
Q11   1   0.8021  0.4667  0.7014  11.00000  0.05    0.26
Q12   1   0.3210 -0.0425  0.6914  11.00000  0.05    0.26
Q13   1   0.8832 -0.0294  0.6724  11.00000  0.05    0.26
Q14   1   0.9270  0.1254  0.8676  11.00000  0.05    0.25
Q15   1   0.8898  0.2045  0.8792  11.00000  0.05    0.23
Q16   1   0.3524  0.1118  0.7746  11.00000  0.05    0.23
Q17   1   0.3917  0.2330  0.8948  11.00000  0.05    0.23
Q18   1   1.0179  0.0214  0.9338  11.00000  0.05    0.22
Q19   1   0.4399  0.0464  0.6225  11.00000  0.05    0.22
Q20   1   0.4475  0.2039  0.4593  11.00000  0.05    0.22
;
_shelx_res_checksum              33463
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_20p2GPa
_database_code_depnum_ccdc_archive 'CCDC 2336591'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_20p2GPa         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.348 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT411_AZO_20p2GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.67 Ang.  
RESPONSE: Intermolecular distances are strongly shortened at high 
pressure and atoms approach closer to one another than at ambient 
conditions or low temperature.
;
_vrf_PLAT149_AZO_20p2GPa         
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.08 Degree
RESPONSE: Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree.
;
_vrf_PLAT911_AZO_20p2GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        520 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3t (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-21
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   11.814(10)
_cell_length_b                   5.5065(2)
_cell_length_c                   10.466(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.17(8)
_cell_angle_gamma                90
_cell_volume                     611.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       20150000
_cell_measurement_reflns_used    488
_cell_measurement_theta_min      2.2360
_cell_measurement_theta_max      20.6190

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.981
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.45539
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         20150000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    1.00    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0385946450
_diffrn_orient_matrix_UB_12      0.0061837213
_diffrn_orient_matrix_UB_13      -0.0213908833
_diffrn_orient_matrix_UB_21      0.0030035946
_diffrn_orient_matrix_UB_22      0.0226452762
_diffrn_orient_matrix_UB_23      -0.0356383375
_diffrn_orient_matrix_UB_31      -0.0023141762
_diffrn_orient_matrix_UB_32      -0.0705537436
_diffrn_orient_matrix_UB_33      -0.0132480989
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2829
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0105
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.245
_diffrn_reflns_theta_max         21.560
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.226
_diffrn_measured_fraction_theta_full 0.348
_diffrn_reflns_Laue_measured_fraction_max 0.226
_diffrn_reflns_Laue_measured_fraction_full 0.348
_diffrn_reflns_point_group_measured_fraction_max 0.226
_diffrn_reflns_point_group_measured_fraction_full 0.348
_reflns_number_total             2829
_reflns_number_gt                2393
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
 Datasets from multiple crystals were merged in shelXL and their reflections 
 were scaled using HKLF 5 with BASF. The BASF parameter was refined to 15.8%. 
 The Uii displacement parameters of all atoms were restrained with ISOR 
 keyword to approximate isotropic behavior.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1421P)²+0.0408P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2829
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_ref         0.1983
_refine_ls_wR_factor_gt          0.1912
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.086
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4905(5) 0.1106(3) 0.5083(3) 0.0143(17) Uani 1 1 d . U . . .
C1 C 0.4217(6) 0.1421(4) 0.5857(4) 0.0150(19) Uani 1 1 d . U . . .
C2 C 0.3799(6) 0.3738(4) 0.5919(4) 0.0132(19) Uani 1 1 d . U . . .
H2 H 0.388040 0.498459 0.536586 0.016 Uiso 1 1 calc R U . . .
C3 C 0.3256(6) 0.4147(4) 0.6826(4) 0.016(2) Uani 1 1 d . U . . .
H3 H 0.294435 0.567926 0.687193 0.019 Uiso 1 1 calc R U . . .
C4 C 0.3173(6) 0.2303(4) 0.7661(4) 0.0147(19) Uani 1 1 d . U . . .
H4 H 0.281096 0.261054 0.827371 0.018 Uiso 1 1 calc R U . . .
C5 C 0.3612(6) 0.0009(4) 0.7614(4) 0.015(2) Uani 1 1 d . U . . .
H5 H 0.358094 -0.120655 0.821443 0.018 Uiso 1 1 calc R U . . .
C6 C 0.4094(6) -0.0454(4) 0.6671(4) 0.0151(19) Uani 1 1 d . U . . .
H6 H 0.433908 -0.202151 0.657352 0.018 Uiso 1 1 calc R U . . .
N2 N 0.9913(5) 0.1098(3) 0.9812(3) 0.0158(18) Uani 1 1 d . U . . .
C7 C 0.9221(6) 0.1364(4) 0.8353(4) 0.0127(19) Uani 1 1 d . U . . .
C8 C 0.9061(6) -0.0537(4) 0.7411(4) 0.0152(19) Uani 1 1 d . U . . .
H8 H 0.930670 -0.210466 0.775137 0.018 Uiso 1 1 calc R U . . .
C9 C 0.8540(6) -0.0079(4) 0.5981(4) 0.015(2) Uani 1 1 d . U . . .
H9 H 0.843255 -0.132199 0.533580 0.017 Uiso 1 1 calc R U . . .
C10 C 0.8179(6) 0.2245(4) 0.5520(4) 0.016(2) Uani 1 1 d . U . . .
H10 H 0.782657 0.257146 0.454889 0.019 Uiso 1 1 calc R U . . .
C11 C 0.8324(6) 0.4107(4) 0.6449(4) 0.0150(19) Uani 1 1 d . U . . .
H11 H 0.806957 0.566831 0.610217 0.018 Uiso 1 1 calc R U . . .
C12 C 0.8839(6) 0.3686(4) 0.7884(4) 0.016(2) Uani 1 1 d . U . . .
H12 H 0.892707 0.493228 0.852118 0.019 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.012(6) 0.0165(10) 0.011(2) -0.0004(8) 0.001(3) 0.0022(12)
C1 0.016(6) 0.0155(9) 0.012(2) 0.0000(9) 0.005(4) 0.0009(13)
C2 0.008(6) 0.0160(10) 0.010(2) 0.0002(9) 0.000(4) 0.0007(13)
C3 0.017(6) 0.0156(10) 0.012(2) -0.0001(9) 0.003(4) 0.0012(14)
C4 0.011(6) 0.0177(10) 0.014(2) 0.0000(9) 0.004(4) 0.0008(14)
C5 0.010(7) 0.0165(11) 0.013(2) 0.0015(9) 0.000(4) 0.0006(14)
C6 0.013(6) 0.0148(10) 0.014(2) -0.0001(9) 0.003(4) 0.0000(14)
N2 0.015(6) 0.0166(10) 0.013(2) 0.0019(8) 0.004(4) 0.0017(12)
C7 0.007(6) 0.0169(10) 0.010(2) 0.0016(9) 0.000(4) 0.0009(13)
C8 0.013(6) 0.0150(10) 0.014(2) 0.0012(9) 0.003(4) 0.0002(14)
C9 0.008(6) 0.0168(11) 0.014(3) 0.0001(9) 0.000(4) -0.0003(14)
C10 0.013(6) 0.0179(10) 0.014(2) 0.0015(9) 0.003(4) 0.0002(14)
C11 0.012(6) 0.0163(10) 0.011(2) 0.0026(9) 0.000(4) 0.0024(14)
C12 0.016(7) 0.0155(11) 0.014(2) 0.0012(9) 0.004(4) 0.0014(14)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.264(4) 3_656 ?
N1 C1 1.389(4) . ?
C1 C2 1.380(4) . ?
C1 C6 1.386(3) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.363(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.260(4) 3_757 ?
N2 C7 1.385(6) . ?
C7 C12 1.373(4) . ?
C7 C8 1.393(4) . ?
C8 C9 1.367(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.368(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.371(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 112.7(3) 3_656 . ?
C2 C1 C6 121.6(3) . . ?
C2 C1 N1 117.2(2) . . ?
C6 C1 N1 120.8(3) . . ?
C3 C2 C1 117.9(2) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 121.6(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 118.9(2) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C1 119.7(2) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N2 N2 C7 112.4(4) 3_757 . ?
C12 C7 N2 115.7(3) . . ?
C12 C7 C8 121.8(3) . . ?
N2 C7 C8 122.1(3) . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 118.6(2) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C9 C10 C11 121.8(3) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 117.8(2) . . ?
C11 C12 H12 121.1 . . ?
C7 C12 H12 121.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -170.7(6) 3_656 . . . ?
N1 N1 C1 C6 17.0(9) 3_656 . . . ?
C6 C1 C2 C3 0.3(9) . . . . ?
N1 C1 C2 C3 -171.9(5) . . . . ?
C1 C2 C3 C4 1.7(9) . . . . ?
C2 C3 C4 C5 -0.6(9) . . . . ?
C3 C4 C5 C6 -2.7(9) . . . . ?
C4 C5 C6 C1 4.7(9) . . . . ?
C2 C1 C6 C5 -3.6(9) . . . . ?
N1 C1 C6 C5 168.4(5) . . . . ?
N2 N2 C7 C12 171.0(5) 3_757 . . . ?
N2 N2 C7 C8 -16.8(8) 3_757 . . . ?
C12 C7 C8 C9 1.7(9) . . . . ?
N2 C7 C8 C9 -170.0(5) . . . . ?
C7 C8 C9 C10 -0.6(8) . . . . ?
C8 C9 C10 C11 -0.2(8) . . . . ?
C9 C10 C11 C12 0.0(9) . . . . ?
C10 C11 C12 C7 1.1(9) . . . . ?
N2 C7 C12 C11 170.2(5) . . . . ?
C8 C7 C12 C11 -2.0(9) . . . . ?


_shelx_res_file                  
;
TITL sample_0159_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 17:42:44 on 21-Mar-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  11.814497   5.506509  10.465879  90.0000 116.1740  90.0000
ZERR    4.00   0.009922   0.000237   0.003802   0.0000   0.0754   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
OMIT -4 -2 1
OMIT 1 1 1
OMIT 2 -1 -5
OMIT -13 0 12
OMIT -3 -1 1
OMIT -2 -1 0
OMIT -2 -1 0
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.03
FMAP 2
PLAN 20
WGHT    0.142100    0.040800
BASF   0.15770
FVAR      25.31062
N1    1    0.490467    0.110554    0.508297    11.00000    0.01170    0.01646 =
         0.01100   -0.00041    0.00147    0.00221
C1    2    0.421680    0.142108    0.585724    11.00000    0.01596    0.01550 =
         0.01191   -0.00003    0.00458    0.00086
C2    2    0.379857    0.373801    0.591888    11.00000    0.00830    0.01603 =
         0.01040    0.00022   -0.00020    0.00072
AFIX  43
H2    3    0.388040    0.498459    0.536586    11.00000   -1.20000
AFIX   0
C3    2    0.325555    0.414703    0.682610    11.00000    0.01681    0.01559 =
         0.01224   -0.00006    0.00347    0.00123
AFIX  43
H3    3    0.294435    0.567926    0.687193    11.00000   -1.20000
AFIX   0
C4    2    0.317283    0.230252    0.766083    11.00000    0.01093    0.01768 =
         0.01353    0.00003    0.00351    0.00079
AFIX  43
H4    3    0.281096    0.261054    0.827371    11.00000   -1.20000
AFIX   0
C5    2    0.361202    0.000857    0.761355    11.00000    0.00953    0.01647 =
         0.01271    0.00146    0.00030    0.00065
AFIX  43
H5    3    0.358094   -0.120655    0.821443    11.00000   -1.20000
AFIX   0
C6    2    0.409391   -0.045434    0.667059    11.00000    0.01314    0.01483 =
         0.01359   -0.00012    0.00254    0.00005
AFIX  43
H6    3    0.433908   -0.202151    0.657352    11.00000   -1.20000
AFIX   0
N2    1    0.991269    0.109798    0.981164    11.00000    0.01498    0.01665 =
         0.01307    0.00190    0.00362    0.00168
C7    2    0.922139    0.136360    0.835320    11.00000    0.00714    0.01692 =
         0.00974    0.00161   -0.00028    0.00091
C8    2    0.906116   -0.053721    0.741093    11.00000    0.01251    0.01501 =
         0.01450    0.00123    0.00255    0.00022
AFIX  43
H8    3    0.930670   -0.210466    0.775137    11.00000   -1.20000
AFIX   0
C9    2    0.853984   -0.007941    0.598116    11.00000    0.00834    0.01677 =
         0.01365    0.00012    0.00041   -0.00035
AFIX  43
H9    3    0.843255   -0.132199    0.533580    11.00000   -1.20000
AFIX   0
C10   2    0.817931    0.224504    0.551978    11.00000    0.01289    0.01790 =
         0.01407    0.00149    0.00300    0.00020
AFIX  43
H10   3    0.782657    0.257146    0.454889    11.00000   -1.20000
AFIX   0
C11   2    0.832370    0.410722    0.644943    11.00000    0.01176    0.01628 =
         0.01150    0.00259    0.00020    0.00238
AFIX  43
H11   3    0.806957    0.566831    0.610217    11.00000   -1.20000
AFIX   0
C12   2    0.883893    0.368580    0.788439    11.00000    0.01609    0.01551 =
         0.01388    0.00117    0.00381    0.00144
AFIX  43
H12   3    0.892707    0.493228    0.852118    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0159_bn1 in P2(1)/c
REM wR2 = 0.198306, GooF = S = 1.10333, Restrained GooF = 1.08670 for all data
REM R1 = 0.066162 for 2393 Fo > 4sig(Fo) and 0.072752 for all 2829 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.1416      0.0406

REM Highest difference peak  0.389,  deepest hole -0.329,  1-sigma level  0.086
Q1    1   0.3599  0.3262  0.7317  11.00000  0.05    0.39
Q2    1   0.8890  0.2424  0.7988  11.00000  0.05    0.39
Q3    1   0.4695  0.2578  0.6468  11.00000  0.05    0.35
Q4    1   0.8143  0.0965  0.5511  11.00000  0.05    0.34
Q5    1   0.3407  0.2549  0.5138  11.00000  0.05    0.32
Q6    1   0.8626  0.3234  0.6174  11.00000  0.05    0.31
Q7    1   0.8520  0.0122  0.6485  11.00000  0.05    0.29
Q8    1   0.7915  0.3057  0.5934  11.00000  0.05    0.28
Q9    1   0.3843  0.0211  0.6312  11.00000  0.05    0.27
Q10   1   0.3635  0.6270  0.7930  11.00000  0.05    0.27
Q11   1   0.8171  0.3223  0.7183  11.00000  0.05    0.27
Q12   1   0.7864  0.4806  0.6918  11.00000  0.05    0.27
Q13   1   1.0509  0.2199  1.0392  11.00000  0.05    0.26
Q14   1   0.1968  0.3965  0.6798  11.00000  0.05    0.26
Q15   1   0.9607  0.0435  0.7995  11.00000  0.05    0.26
Q16   1   0.8406  0.3214  0.4851  11.00000  0.05    0.25
Q17   1   0.3683  0.0059  0.7170  11.00000  0.05    0.25
Q18   1   0.9471  0.1284  0.8954  11.00000  0.05    0.25
Q19   1   0.7121  0.2229  0.6042  11.00000  0.05    0.24
Q20   1   0.4550  0.2234  0.4569  11.00000  0.05    0.24
;
_shelx_res_checksum              12336
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_17p6GPa
_database_code_depnum_ccdc_archive 'CCDC 2336583'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_17p6GPa         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.349 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT411_AZO_17p6GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.69 Ang.  
RESPONSE: Intermolecular distances are strongly shortened at high 
pressure and atoms approach closer to one another than at ambient 
conditions or low temperature.
;
_vrf_PLAT149_AZO_17p6GPa         
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.10 Degree
RESPONSE: Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree.
;
_vrf_PLAT911_AZO_17p6GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        567 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3s (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-16
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   11.979(13)
_cell_length_b                   5.5148(4)
_cell_length_c                   10.530(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.74(10)
_cell_angle_gamma                90
_cell_volume                     626.6(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       17620000
_cell_measurement_reflns_used    487
_cell_measurement_theta_min      3.0790
_cell_measurement_theta_max      21.2440

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.932
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.41427
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         17620000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    1.00    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0378752491
_diffrn_orient_matrix_UB_12      0.0065508967
_diffrn_orient_matrix_UB_13      -0.0210919654
_diffrn_orient_matrix_UB_21      0.0031659879
_diffrn_orient_matrix_UB_22      0.0223367384
_diffrn_orient_matrix_UB_23      -0.0353915845
_diffrn_orient_matrix_UB_31      -0.0023549848
_diffrn_orient_matrix_UB_32      -0.0705314630
_diffrn_orient_matrix_UB_33      -0.0130406426
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2667
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0107
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.231
_diffrn_reflns_theta_max         21.463
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.207
_diffrn_measured_fraction_theta_full 0.349
_diffrn_reflns_Laue_measured_fraction_max 0.207
_diffrn_reflns_Laue_measured_fraction_full 0.349
_diffrn_reflns_point_group_measured_fraction_max 0.207
_diffrn_reflns_point_group_measured_fraction_full 0.349
_reflns_number_total             2667
_reflns_number_gt                2173
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
 Datasets from multiple crystals were merged in shelXL and their reflections 
 were scaled using HKLF 5 with BASF. The BASF parameter was refined to 43.9%. 
 The Uii displacement parameters of all atoms were restrained with ISOR 
 keyword to approximate isotropic behavior.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1362P)²+0.0061P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2667
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1867
_refine_ls_wR_factor_gt          0.1788
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.059
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4905(5) 0.1104(3) 0.5082(3) 0.0193(15) Uani 1 1 d . U . . .
C1 C 0.4224(6) 0.1416(4) 0.5857(4) 0.0209(16) Uani 1 1 d . U . . .
C2 C 0.3807(6) 0.3727(4) 0.5911(4) 0.0177(17) Uani 1 1 d . U . . .
H2 H 0.389479 0.496952 0.536471 0.021 Uiso 1 1 calc R U . . .
C3 C 0.3255(6) 0.4140(4) 0.6802(4) 0.0206(17) Uani 1 1 d . U . . .
H3 H 0.293529 0.566438 0.683261 0.025 Uiso 1 1 calc R U . . .
C4 C 0.3176(6) 0.2312(4) 0.7642(4) 0.0205(17) Uani 1 1 d . U . . .
H4 H 0.281656 0.262557 0.825031 0.025 Uiso 1 1 calc R U . . .
C5 C 0.3617(6) 0.0026(4) 0.7604(4) 0.0204(17) Uani 1 1 d . U . . .
H5 H 0.358233 -0.118325 0.820113 0.024 Uiso 1 1 calc R U . . .
C6 C 0.4107(5) -0.0444(4) 0.6675(4) 0.0187(16) Uani 1 1 d . U . . .
H6 H 0.436014 -0.200653 0.659175 0.022 Uiso 1 1 calc R U . . .
N2 N 0.9904(5) 0.1090(3) 0.9807(3) 0.0197(15) Uani 1 1 d . U . . .
C7 C 0.9220(6) 0.1332(4) 0.8352(4) 0.0188(16) Uani 1 1 d . U . . .
C8 C 0.9081(5) -0.0568(4) 0.7429(4) 0.0207(17) Uani 1 1 d . U . . .
H8 H 0.933961 -0.212406 0.777120 0.025 Uiso 1 1 calc R U . . .
C9 C 0.8559(6) -0.0121(4) 0.6007(4) 0.0217(18) Uani 1 1 d . U . . .
H9 H 0.846302 -0.136478 0.537147 0.026 Uiso 1 1 calc R U . . .
C10 C 0.8179(6) 0.2191(4) 0.5538(4) 0.0225(18) Uani 1 1 d . U . . .
H10 H 0.782229 0.250451 0.457475 0.027 Uiso 1 1 calc R U . . .
C11 C 0.8315(6) 0.4053(4) 0.6460(4) 0.0213(17) Uani 1 1 d . U . . .
H11 H 0.805740 0.560734 0.611516 0.026 Uiso 1 1 calc R U . . .
C12 C 0.8825(6) 0.3639(4) 0.7882(4) 0.0220(17) Uani 1 1 d . U . . .
H12 H 0.890197 0.488332 0.851125 0.026 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.022(5) 0.0213(10) 0.0150(19) -0.0003(7) 0.008(3) 0.0017(11)
C1 0.028(5) 0.0205(9) 0.017(2) -0.0002(8) 0.012(3) 0.0009(13)
C2 0.016(5) 0.0215(10) 0.013(2) -0.0002(8) 0.004(3) 0.0000(13)
C3 0.025(5) 0.0199(10) 0.016(2) -0.0005(8) 0.008(3) 0.0008(13)
C4 0.022(5) 0.0231(10) 0.017(2) 0.0000(9) 0.009(3) 0.0006(14)
C5 0.022(5) 0.0213(11) 0.017(2) 0.0016(9) 0.007(3) 0.0010(13)
C6 0.019(5) 0.0192(9) 0.016(2) -0.0006(8) 0.006(3) -0.0007(13)
N2 0.021(5) 0.0218(10) 0.015(2) 0.0012(8) 0.007(3) 0.0006(11)
C7 0.020(5) 0.0215(10) 0.014(2) 0.0014(8) 0.007(3) 0.0007(13)
C8 0.024(5) 0.0196(9) 0.019(2) 0.0015(9) 0.009(3) -0.0001(13)
C9 0.024(6) 0.0222(11) 0.019(2) -0.0008(9) 0.010(3) -0.0018(13)
C10 0.027(6) 0.0225(10) 0.018(2) 0.0013(9) 0.009(3) -0.0010(14)
C11 0.025(5) 0.0216(10) 0.017(2) 0.0022(8) 0.009(3) 0.0013(13)
C12 0.028(5) 0.0206(10) 0.017(2) 0.0011(9) 0.010(3) 0.0009(13)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.264(4) 3_656 ?
N1 C1 1.393(4) . ?
C1 C2 1.379(4) . ?
C1 C6 1.385(3) . ?
C2 C3 1.382(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.366(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.258(4) 3_757 ?
N2 C7 1.395(6) . ?
C7 C12 1.372(4) . ?
C7 C8 1.390(3) . ?
C8 C9 1.371(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 112.6(3) 3_656 . ?
C2 C1 C6 121.5(2) . . ?
C2 C1 N1 116.9(2) . . ?
C6 C1 N1 121.1(3) . . ?
C1 C2 C3 118.0(2) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 119.7(2) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2 N2 C7 112.6(4) 3_757 . ?
C12 C7 C8 122.0(3) . . ?
C12 C7 N2 115.5(3) . . ?
C8 C7 N2 122.1(3) . . ?
C9 C8 C7 119.2(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 118.9(2) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C9 C10 C11 121.4(3) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 118.0(2) . . ?
C11 C12 H12 121.0 . . ?
C7 C12 H12 121.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -170.4(6) 3_656 . . . ?
N1 N1 C1 C6 17.4(8) 3_656 . . . ?
C6 C1 C2 C3 -0.5(9) . . . . ?
N1 C1 C2 C3 -172.7(5) . . . . ?
C1 C2 C3 C4 2.6(8) . . . . ?
C2 C3 C4 C5 -1.3(9) . . . . ?
C3 C4 C5 C6 -2.1(9) . . . . ?
C4 C5 C6 C1 4.1(9) . . . . ?
C2 C1 C6 C5 -2.9(9) . . . . ?
N1 C1 C6 C5 169.0(5) . . . . ?
N2 N2 C7 C12 171.0(5) 3_757 . . . ?
N2 N2 C7 C8 -16.7(8) 3_757 . . . ?
C12 C7 C8 C9 1.4(8) . . . . ?
N2 C7 C8 C9 -170.4(5) . . . . ?
C7 C8 C9 C10 -0.5(8) . . . . ?
C8 C9 C10 C11 0.1(8) . . . . ?
C9 C10 C11 C12 -0.7(8) . . . . ?
C10 C11 C12 C7 1.5(9) . . . . ?
C8 C7 C12 C11 -1.9(8) . . . . ?
N2 C7 C12 C11 170.4(5) . . . . ?


_shelx_res_file                  
;
TITL sample_0148_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 10:45:32 on 27-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  11.979272   5.514761  10.529960  90.0000 115.7450  90.0000
ZERR    4.00   0.013418   0.000409   0.005003   0.0000   0.0991   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.136200    0.006100
BASF   0.43907
FVAR      29.73512
N1    1    0.490536    0.110394    0.508181    11.00000    0.02178    0.02125 =
         0.01502   -0.00028    0.00812    0.00174
C1    2    0.422401    0.141555    0.585732    11.00000    0.02826    0.02050 =
         0.01680   -0.00022    0.01234    0.00093
C2    2    0.380696    0.372670    0.591145    11.00000    0.01638    0.02148 =
         0.01275   -0.00018    0.00399   -0.00004
AFIX  43
H2    3    0.389479    0.496952    0.536471    11.00000   -1.20000
AFIX   0
C3    2    0.325480    0.413990    0.680237    11.00000    0.02538    0.01989 =
         0.01586   -0.00046    0.00829    0.00079
AFIX  43
H3    3    0.293529    0.566438    0.683261    11.00000   -1.20000
AFIX   0
C4    2    0.317590    0.231203    0.764208    11.00000    0.02230    0.02309 =
         0.01687   -0.00004    0.00911    0.00056
AFIX  43
H4    3    0.281656    0.262557    0.825031    11.00000   -1.20000
AFIX   0
C5    2    0.361684    0.002600    0.760361    11.00000    0.02196    0.02130 =
         0.01697    0.00155    0.00750    0.00102
AFIX  43
H5    3    0.358233   -0.118325    0.820113    11.00000   -1.20000
AFIX   0
C6    2    0.410670   -0.044449    0.667469    11.00000    0.01929    0.01921 =
         0.01618   -0.00063    0.00630   -0.00071
AFIX  43
H6    3    0.436014   -0.200653    0.659175    11.00000   -1.20000
AFIX   0
N2    1    0.990382    0.109031    0.980691    11.00000    0.02144    0.02182 =
         0.01478    0.00117    0.00680    0.00062
C7    2    0.922009    0.133245    0.835222    11.00000    0.02041    0.02151 =
         0.01370    0.00142    0.00656    0.00075
C8    2    0.908125   -0.056826    0.742897    11.00000    0.02359    0.01961 =
         0.01907    0.00146    0.00948   -0.00014
AFIX  43
H8    3    0.933961   -0.212406    0.777120    11.00000   -1.20000
AFIX   0
C9    2    0.855860   -0.012119    0.600714    11.00000    0.02423    0.02216 =
         0.01882   -0.00084    0.00951   -0.00175
AFIX  43
H9    3    0.846302   -0.136478    0.537147    11.00000   -1.20000
AFIX   0
C10   2    0.817912    0.219075    0.553806    11.00000    0.02651    0.02246 =
         0.01789    0.00129    0.00918   -0.00103
AFIX  43
H10   3    0.782229    0.250451    0.457475    11.00000   -1.20000
AFIX   0
C11   2    0.831466    0.405251    0.646012    11.00000    0.02541    0.02158 =
         0.01669    0.00220    0.00886    0.00131
AFIX  43
H11   3    0.805740    0.560734    0.611516    11.00000   -1.20000
AFIX   0
C12   2    0.882511    0.363903    0.788237    11.00000    0.02822    0.02061 =
         0.01708    0.00112    0.00989    0.00094
AFIX  43
H12   3    0.890197    0.488332    0.851125    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0148_bn1 in P2(1)/c
REM wR2 = 0.1867, GooF = S = 1.102, Restrained GooF = 1.089 for all data
REM R1 = 0.0624 for 2173 Fo > 4sig(Fo) and 0.0719 for all 2667 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.1362      0.0061

REM Highest difference peak  0.288,  deepest hole -0.240,  1-sigma level  0.059
Q1    1   0.3561  0.3137  0.7325  11.00000  0.05    0.29
Q2    1   0.9682  0.0364  0.8107  11.00000  0.05    0.26
Q3    1   0.8881  0.2350  0.7985  11.00000  0.05    0.25
Q4    1   0.8801  0.3102  0.6206  11.00000  0.05    0.24
Q5    1   0.3786  0.3918  0.6466  11.00000  0.05    0.24
Q6    1   0.8123  0.0868  0.5517  11.00000  0.05    0.24
Q7    1   0.2585  0.3190  0.6908  11.00000  0.05    0.24
Q8    1   0.4035  0.2423  0.5801  11.00000  0.05    0.24
Q9    1   0.8855  0.1443  0.5977  11.00000  0.05    0.23
Q10   1   0.8770  0.0420  0.7866  11.00000  0.05    0.23
Q11   1   0.8666  0.4045  0.7327  11.00000  0.05    0.23
Q12   1   0.8107  0.2932  0.6061  11.00000  0.05    0.22
Q13   1   0.7407  0.3607  0.5797  11.00000  0.05    0.21
Q14   1   0.8689 -0.0357  0.6621  11.00000  0.05    0.20
Q15   1   0.8100  0.3278  0.7019  11.00000  0.05    0.20
Q16   1   0.3497  0.1088  0.7687  11.00000  0.05    0.20
Q17   1   0.8045  0.4546  0.7012  11.00000  0.05    0.19
Q18   1   0.4368  0.0507  0.6256  11.00000  0.05    0.19
Q19   1   0.3231 -0.0439  0.6908  11.00000  0.05    0.18
Q20   1   0.4698  0.2218  0.4722  11.00000  0.05    0.18
;
_shelx_res_checksum              27752
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_1p5GPa
_database_code_depnum_ccdc_archive 'CCDC 2336589'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_1p5GPa          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.349 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT149_AZO_1p5GPa          
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.07 Degree
RESPONSE: Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree.
;
_vrf_PLAT911_AZO_1p5GPa          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        669 Report
RESPONSE:  Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3r (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-15
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   14.547(13)
_cell_length_b                   5.5258(3)
_cell_length_c                   11.659(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.40(7)
_cell_angle_gamma                90
_cell_volume                     866.5(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       1513000
_cell_measurement_reflns_used    426
_cell_measurement_theta_min      2.2110
_cell_measurement_theta_max      20.5960

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.038
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.23878
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         1513000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    0.50    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.0302311043
_diffrn_orient_matrix_UB_12      0.0062797562
_diffrn_orient_matrix_UB_13      0.0177904356
_diffrn_orient_matrix_UB_21      -0.0035535390
_diffrn_orient_matrix_UB_22      0.0197920863
_diffrn_orient_matrix_UB_23      0.0319471627
_diffrn_orient_matrix_UB_31      0.0016687863
_diffrn_orient_matrix_UB_32      -0.0712413295
_diffrn_orient_matrix_UB_33      0.0104479785
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            4050
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.016
_diffrn_reflns_theta_max         21.065
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.214
_diffrn_measured_fraction_theta_full 0.349
_diffrn_reflns_Laue_measured_fraction_max 0.214
_diffrn_reflns_Laue_measured_fraction_full 0.349
_diffrn_reflns_point_group_measured_fraction_max 0.214
_diffrn_reflns_point_group_measured_fraction_full 0.349
_reflns_number_total             4050
_reflns_number_gt                3314
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
The BASF parameter was refined to 47%. The anisotropic displacement 
parameters of the disordered nitrogen atoms N2A and N2B were restrained to 
similar behaviour using SIMU restraint. The anisotropic displacement 
parameters of all atoms were restrained to isotropic behqaviour using ISOR 
restraint.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1072P)²+0.0353P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4050
_refine_ls_number_parameters     138
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1708
_refine_ls_wR_factor_gt          0.1621
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.047
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4893(3) 0.1080(3) 0.5054(2) 0.0267(10) Uani 1 1 d . U . . .
C1 C 0.4316(3) 0.1399(3) 0.5787(2) 0.0229(10) Uani 1 1 d . U . . .
C2 C 0.3820(3) 0.3591(3) 0.5658(2) 0.0282(11) Uani 1 1 d . U . . .
H2 H 0.387635 0.475473 0.511261 0.034 Uiso 1 1 calc R U . . .
C3 C 0.3241(3) 0.4044(3) 0.6339(3) 0.0306(11) Uani 1 1 d . U . . .
H3 H 0.288839 0.548671 0.622840 0.037 Uiso 1 1 calc R U . . .
C4 C 0.3188(3) 0.2342(4) 0.7191(3) 0.0306(12) Uani 1 1 d . U . . .
H4 H 0.280335 0.264812 0.765568 0.037 Uiso 1 1 calc R U . . .
C5 C 0.3711(3) 0.0183(3) 0.7344(3) 0.0280(12) Uani 1 1 d . U . . .
H5 H 0.368968 -0.093235 0.793123 0.034 Uiso 1 1 calc R U . . .
C6 C 0.4263(3) -0.0330(3) 0.6636(2) 0.0240(10) Uani 1 1 d . U . . .
H6 H 0.459332 -0.180021 0.672279 0.029 Uiso 1 1 calc R U . . .
N2A N 0.9671(5) 0.0768(4) 0.9758(5) 0.0347(15) Uani 0.934(12) 1 d . U P A 1
N2B N 0.991(7) -0.094(6) 0.960(7) 0.035(4) Uani 0.066(12) 1 d . U P A 2
C7 C 0.9187(3) 0.0539(4) 0.8455(3) 0.0312(13) Uani 1 1 d . U . . .
C8 C 0.9281(4) -0.1427(4) 0.7747(3) 0.0352(14) Uani 1 1 d . U . . .
H8 H 0.968791 -0.273049 0.812722 0.042 Uiso 1 1 calc R U . . .
C9 C 0.8764(4) -0.1402(4) 0.6481(3) 0.0392(15) Uani 1 1 d . U . . .
H9 H 0.882352 -0.270022 0.600601 0.047 Uiso 1 1 calc R U . . .
C10 C 0.8156(4) 0.0537(5) 0.5905(3) 0.0383(16) Uani 1 1 d . U . . .
H10 H 0.780752 0.053303 0.504995 0.046 Uiso 1 1 calc R U . . .
C11 C 0.8072(4) 0.2482(4) 0.6613(3) 0.0399(16) Uani 1 1 d . U . . .
H11 H 0.767580 0.379986 0.623039 0.048 Uiso 1 1 calc R U . . .
C12 C 0.8570(4) 0.2461(4) 0.7871(3) 0.0358(14) Uani 1 1 d . U . . .
H12 H 0.849571 0.374820 0.834238 0.043 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.031(3) 0.0263(8) 0.0267(13) -0.0005(5) 0.0152(19) 0.0015(8)
C1 0.024(3) 0.0241(8) 0.0212(14) -0.0012(6) 0.009(2) 0.0009(8)
C2 0.033(4) 0.0251(9) 0.0280(16) 0.0014(6) 0.013(2) 0.0036(9)
C3 0.031(4) 0.0273(9) 0.0372(17) -0.0027(7) 0.017(2) 0.0045(10)
C4 0.029(4) 0.0358(10) 0.0317(18) -0.0054(7) 0.017(3) -0.0007(10)
C5 0.027(4) 0.0335(10) 0.0258(16) 0.0007(7) 0.013(2) -0.0013(10)
C6 0.024(3) 0.0250(8) 0.0237(14) 0.0008(6) 0.010(2) 0.0014(8)
N2A 0.039(4) 0.0380(11) 0.027(3) 0.0022(9) 0.013(3) 0.0057(12)
N2B 0.040(7) 0.037(6) 0.028(6) 0.003(6) 0.011(7) 0.005(6)
C7 0.028(4) 0.0385(11) 0.0288(18) 0.0042(8) 0.013(3) 0.0011(11)
C8 0.033(4) 0.0351(11) 0.040(2) 0.0022(8) 0.016(3) 0.0026(11)
C9 0.038(5) 0.0428(12) 0.040(2) -0.0085(10) 0.019(3) -0.0039(13)
C10 0.034(5) 0.0535(14) 0.027(2) 0.0013(10) 0.011(3) -0.0041(15)
C11 0.039(5) 0.0423(13) 0.039(2) 0.0100(9) 0.016(3) 0.0077(13)
C12 0.039(5) 0.0374(11) 0.0330(19) 0.0011(8) 0.016(3) 0.0025(12)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.252(3) 3_656 ?
N1 C1 1.419(3) . ?
C1 C2 1.388(3) . ?
C1 C6 1.399(2) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2A N2A 1.242(10) 3_757 ?
N2A C7 1.416(6) . ?
N2B N2B 1.35(11) 3_757 ?
N2B C7 1.58(7) . ?
C7 C12 1.389(5) . ?
C7 C8 1.403(3) . ?
C8 C9 1.378(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.389(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 114.0(2) 3_656 . ?
C2 C1 C6 120.4(2) . . ?
C2 C1 N1 116.47(16) . . ?
C6 C1 N1 123.1(2) . . ?
C3 C2 C1 120.07(17) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C6 C5 C4 120.88(18) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 118.9(2) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N2A N2A C7 114.1(4) 3_757 . ?
N2B N2B C7 94(5) 3_757 . ?
C12 C7 C8 119.6(3) . . ?
C12 C7 N2A 115.0(2) . . ?
C8 C7 N2A 125.5(3) . . ?
C12 C7 N2B 155.4(17) . . ?
C8 C7 N2B 85.0(18) . . ?
C9 C8 C7 119.1(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 120.9(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 120.8(2) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -162.1(4) 3_656 . . . ?
N1 N1 C1 C6 20.1(6) 3_656 . . . ?
C6 C1 C2 C3 -2.2(6) . . . . ?
N1 C1 C2 C3 180.0(3) . . . . ?
C1 C2 C3 C4 2.5(6) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
C3 C4 C5 C6 -1.9(6) . . . . ?
C4 C5 C6 C1 2.2(6) . . . . ?
C2 C1 C6 C5 -0.1(5) . . . . ?
N1 C1 C6 C5 177.5(3) . . . . ?
N2A N2A C7 C12 -169.7(5) 3_757 . . . ?
N2A N2A C7 C8 10.6(7) 3_757 . . . ?
N2B N2B C7 C12 -16(11) 3_757 . . . ?
N2B N2B C7 C8 168(6) 3_757 . . . ?
C12 C7 C8 C9 0.5(5) . . . . ?
N2A C7 C8 C9 -179.9(4) . . . . ?
N2B C7 C8 C9 179(2) . . . . ?
C7 C8 C9 C10 0.1(6) . . . . ?
C8 C9 C10 C11 0.3(6) . . . . ?
C9 C10 C11 C12 -1.3(6) . . . . ?
C10 C11 C12 C7 1.8(6) . . . . ?
C8 C7 C12 C11 -1.4(6) . . . . ?
N2A C7 C12 C11 178.9(4) . . . . ?
N2B C7 C12 C11 -177(6) . . . . ?


_shelx_res_file                  
;
TITL sample_0025_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 15:02:02 on 24-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  14.546824   5.525760  11.659318  90.0000 112.3992  90.0000
ZERR    4.00   0.012806   0.000342   0.003884   0.0000   0.0710   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
OMIT 3 -1 -1
OMIT -3 1 1
OMIT -2 1 -1
OMIT 2 -1 0
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.03
FMAP 2
PLAN 20
WGHT    0.107200    0.035300
BASF   0.46970
FVAR      23.66814   0.93449
N1    1    0.489300    0.107966    0.505411    11.00000    0.03092    0.02630 =
         0.02666   -0.00045    0.01520    0.00154
C1    2    0.431583    0.139939    0.578719    11.00000    0.02389    0.02406 =
         0.02118   -0.00118    0.00892    0.00094
C2    2    0.381964    0.359076    0.565805    11.00000    0.03303    0.02509 =
         0.02800    0.00140    0.01341    0.00358
AFIX  43
H2    3    0.387635    0.475473    0.511261    11.00000   -1.20000
AFIX   0
C3    2    0.324137    0.404447    0.633930    11.00000    0.03090    0.02735 =
         0.03722   -0.00272    0.01697    0.00452
AFIX  43
H3    3    0.288839    0.548671    0.622840    11.00000   -1.20000
AFIX   0
C4    2    0.318757    0.234225    0.719122    11.00000    0.02889    0.03576 =
         0.03168   -0.00542    0.01674   -0.00074
AFIX  43
H4    3    0.280335    0.264812    0.765568    11.00000   -1.20000
AFIX   0
C5    2    0.371093    0.018286    0.734444    11.00000    0.02721    0.03353 =
         0.02577    0.00067    0.01294   -0.00132
AFIX  43
H5    3    0.368968   -0.093235    0.793123    11.00000   -1.20000
AFIX   0
C6    2    0.426273   -0.032951    0.663616    11.00000    0.02379    0.02500 =
         0.02374    0.00081    0.00961    0.00138
AFIX  43
H6    3    0.459332   -0.180021    0.672279    11.00000   -1.20000
AFIX   0
SIMU 0.003 N2A N2B
PART 1 21.
N2A   1    0.967145    0.076817    0.975825    21.00000    0.03872    0.03799 =
         0.02728    0.00223    0.01252    0.00573
PART 2 -21.
N2B   1    0.991088   -0.093959    0.960013   -21.00000    0.03954    0.03714 =
         0.02755    0.00298    0.01054    0.00490
PART 0
C7    2    0.918656    0.053934    0.845540    11.00000    0.02834    0.03846 =
         0.02877    0.00416    0.01314    0.00108
C8    2    0.928146   -0.142719    0.774718    11.00000    0.03279    0.03513 =
         0.03985    0.00220    0.01620    0.00259
AFIX  43
H8    3    0.968791   -0.273049    0.812722    11.00000   -1.20000
AFIX   0
C9    2    0.876438   -0.140194    0.648088    11.00000    0.03823    0.04282 =
         0.04034   -0.00849    0.01928   -0.00392
AFIX  43
H9    3    0.882352   -0.270022    0.600601    11.00000   -1.20000
AFIX   0
C10   2    0.815608    0.053709    0.590456    11.00000    0.03431    0.05348 =
         0.02656    0.00131    0.01082   -0.00414
AFIX  43
H10   3    0.780752    0.053303    0.504995    11.00000   -1.20000
AFIX   0
C11   2    0.807169    0.248216    0.661275    11.00000    0.03901    0.04231 =
         0.03941    0.00999    0.01627    0.00775
AFIX  43
H11   3    0.767580    0.379986    0.623039    11.00000   -1.20000
AFIX   0
C12   2    0.857016    0.246066    0.787131    11.00000    0.03864    0.03745 =
         0.03301    0.00113    0.01565    0.00252
AFIX  43
H12   3    0.849571    0.374820    0.834238    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0025_bn1 in P2(1)/c
REM wR2 = 0.1708, GooF = S = 1.071, Restrained GooF = 1.058 for all data
REM R1 = 0.0586 for 3314 Fo > 4sig(Fo) and 0.0687 for all 4050 data
REM 138 parameters refined using 96 restraints

END

WGHT      0.1074      0.0346

REM Highest difference peak  0.257,  deepest hole -0.199,  1-sigma level  0.047
Q1    1   0.4200  0.2514  0.5895  11.00000  0.05    0.26
Q2    1   0.3172  0.3154  0.6737  11.00000  0.05    0.24
Q3    1   0.3434  0.3599  0.5976  11.00000  0.05    0.24
Q4    1   0.3829  0.2208  0.5463  11.00000  0.05    0.23
Q5    1   0.9198 -0.0473  0.8207  11.00000  0.05    0.23
Q6    1   0.4282  0.0540  0.6220  11.00000  0.05    0.23
Q7    1   0.4202  0.0197  0.7112  11.00000  0.05    0.21
Q8    1   0.3766 -0.0289  0.6849  11.00000  0.05    0.21
Q9    1   0.5015  0.2067  0.4692  11.00000  0.05    0.20
Q10   1   0.9080  0.1666  0.8207  11.00000  0.05    0.19
Q11   1   0.8033  0.1454  0.6183  11.00000  0.05    0.18
Q12   1   0.8423  0.2450  0.7301  11.00000  0.05    0.17
Q13   1   0.5550  0.1443  0.5138  11.00000  0.05    0.17
Q14   1   0.3447  0.0641  0.5378  11.00000  0.05    0.16
Q15   1   0.4392  0.0929  0.5299  11.00000  0.05    0.15
Q16   1   0.8210 -0.0618  0.6116  11.00000  0.05    0.14
Q17   1   0.7541 -0.2622  0.5057  11.00000  0.05    0.14
Q18   1   0.2915  0.2790  0.4856  11.00000  0.05    0.14
Q19   1   0.3704 -0.0275  0.5826  11.00000  0.05    0.14
Q20   1   0.3685  0.1440  0.7512  11.00000  0.05    0.13
;
_shelx_res_checksum              71470
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZO_19p6GPa
_database_code_depnum_ccdc_archive 'CCDC 2336587'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_AZO_19p6GPa         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.355 Why?  
RESPONSE: Data were collected from two single crystals of different
orientation loaded within a diamond anvil high-pressure cell. Data of
both crystals were merged. Still a large part of reciprocal space
was shadowed by the pressure cell.
;
_vrf_PLAT411_AZO_19p6GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.67 Ang.  
RESPONSE: Intermolecular distances are strongly shortened at high 
pressure and atoms approach closer to one another than at ambient 
conditions or low temperature.
;
_vrf_PLAT149_AZO_19p6GPa         
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.07 Degree
RESPONSE: Unit cell parameters were obtained from one single crystal loaded 
within a diamond anvil high-pressure cell with an opening angle of 64 degree.
;
_vrf_PLAT911_AZO_19p6GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        524 Report
RESPONSE: Data were collected from single crystals loaded within a 
diamond anvil high-pressure cell. Hence, a large part of reciprocal space
was shadowed by the pressure cell.
;
# end Validation Reply Form

_audit_creation_method           'CIF-fill 1.3t (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-21
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
alexandra.friedrich1@uni-wuerzburg.de
k.radacki@uni-wuerzburg.de
agati@lens.unifi.it
romi@lens.unifi.it
fanetti@lens.unifi.it
roberto.bini@unifi.it
hanfland@esrf.fr
holger.braunschweig@uni-wuerzburg.de
todd.marder@uni-wuerzburg.de
_chemical_name_systematic        trans-azobenzene
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_shelx_space_group_comment       
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   11.834(10)
_cell_length_b                   5.5100(3)
_cell_length_c                   10.478(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.14(7)
_cell_angle_gamma                90
_cell_volume                     613.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       19630000
_cell_measurement_reflns_used    493
_cell_measurement_theta_min      2.2340
_cell_measurement_theta_max      20.4040

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.973
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.43322
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_diffrn_ambient_temperature      298(2)
_diffrn_ambient_pressure         19630000
_diffrn_ambient_environment      He
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.410
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    1.00    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0385018754
_diffrn_orient_matrix_UB_12      0.0062425055
_diffrn_orient_matrix_UB_13      -0.0213569498
_diffrn_orient_matrix_UB_21      0.0030286070
_diffrn_orient_matrix_UB_22      0.0226117657
_diffrn_orient_matrix_UB_23      -0.0355922631
_diffrn_orient_matrix_UB_31      -0.0023159630
_diffrn_orient_matrix_UB_32      -0.0705247131
_diffrn_orient_matrix_UB_33      -0.0132234153
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2815
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0119
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.242
_diffrn_reflns_theta_max         21.539
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.229
_diffrn_measured_fraction_theta_full 0.355
_diffrn_reflns_Laue_measured_fraction_max 0.229
_diffrn_reflns_Laue_measured_fraction_full 0.355
_diffrn_reflns_point_group_measured_fraction_max 0.229
_diffrn_reflns_point_group_measured_fraction_full 0.355
_reflns_number_total             2815
_reflns_number_gt                2376
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       'ESRF ID15B beamline software'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
 Datasets from multiple crystals were merged in shelXL and their reflections 
 were scaled using HKLF 5 with BASF. The BASF parameter was refined to 19%. 
 The Uii displacement parameters of all atoms were restrained with ISOR 
 keyword to approximate isotropic behavior.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1572P)²+0.0253P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2815
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0722
_refine_ls_wR_factor_ref         0.2130
_refine_ls_wR_factor_gt          0.2069
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.090
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4906(5) 0.1106(3) 0.5083(4) 0.0163(18) Uani 1 1 d . U . . .
C1 C 0.4217(6) 0.1420(4) 0.5857(4) 0.016(2) Uani 1 1 d . U . . .
C2 C 0.3802(6) 0.3736(4) 0.5918(4) 0.015(2) Uani 1 1 d . U . . .
H2 H 0.388828 0.498276 0.536949 0.018 Uiso 1 1 calc R U . . .
C3 C 0.3253(6) 0.4146(4) 0.6821(4) 0.018(2) Uani 1 1 d . U . . .
H3 H 0.294015 0.567621 0.686471 0.021 Uiso 1 1 calc R U . . .
C4 C 0.3167(6) 0.2304(4) 0.7653(4) 0.0160(19) Uani 1 1 d . U . . .
H4 H 0.280020 0.260960 0.825969 0.019 Uiso 1 1 calc R U . . .
C5 C 0.3612(6) 0.0011(4) 0.7612(4) 0.016(2) Uani 1 1 d . U . . .
H5 H 0.358611 -0.119921 0.821672 0.019 Uiso 1 1 calc R U . . .
C6 C 0.4092(6) -0.0455(4) 0.6668(4) 0.017(2) Uani 1 1 d . U . . .
H6 H 0.433493 -0.202290 0.656979 0.020 Uiso 1 1 calc R U . . .
N2 N 0.9914(5) 0.1095(3) 0.9812(4) 0.0186(19) Uani 1 1 d . U . . .
C7 C 0.9221(6) 0.1360(4) 0.8352(4) 0.014(2) Uani 1 1 d . U . . .
C8 C 0.9065(6) -0.0542(4) 0.7415(4) 0.017(2) Uani 1 1 d . U . . .
H8 H 0.931252 -0.210689 0.775627 0.020 Uiso 1 1 calc R U . . .
C9 C 0.8541(6) -0.0085(4) 0.5984(4) 0.015(2) Uani 1 1 d . U . . .
H9 H 0.843442 -0.132693 0.533975 0.018 Uiso 1 1 calc R U . . .
C10 C 0.8179(6) 0.2238(4) 0.5522(4) 0.018(2) Uani 1 1 d . U . . .
H10 H 0.782572 0.256358 0.455267 0.022 Uiso 1 1 calc R U . . .
C11 C 0.8323(7) 0.4101(4) 0.6452(4) 0.017(2) Uani 1 1 d . U . . .
H11 H 0.806873 0.566143 0.610538 0.020 Uiso 1 1 calc R U . . .
C12 C 0.8837(6) 0.3678(4) 0.7884(4) 0.017(2) Uani 1 1 d . U . . .
H12 H 0.892382 0.492267 0.852005 0.021 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.016(6) 0.0162(10) 0.013(2) -0.0005(8) 0.003(4) 0.0020(12)
C1 0.020(6) 0.0148(10) 0.013(2) -0.0002(9) 0.005(4) 0.0007(13)
C2 0.013(7) 0.0161(11) 0.011(3) 0.0000(9) 0.000(4) 0.0004(14)
C3 0.021(7) 0.0155(10) 0.014(2) -0.0002(9) 0.005(4) 0.0011(14)
C4 0.014(6) 0.0176(11) 0.014(2) 0.0000(9) 0.004(4) 0.0012(14)
C5 0.013(7) 0.0163(11) 0.013(3) 0.0010(10) 0.000(4) 0.0005(15)
C6 0.017(6) 0.0145(10) 0.014(2) -0.0002(9) 0.003(4) -0.0003(14)
N2 0.022(6) 0.0168(11) 0.015(2) 0.0022(8) 0.006(4) 0.0021(12)
C7 0.011(6) 0.0165(11) 0.011(3) 0.0019(9) 0.001(4) 0.0014(13)
C8 0.016(6) 0.0147(10) 0.015(3) 0.0019(9) 0.003(4) 0.0008(14)
C9 0.008(7) 0.0168(11) 0.014(3) -0.0004(9) -0.001(4) -0.0012(14)
C10 0.018(7) 0.0177(11) 0.016(3) 0.0018(10) 0.005(4) 0.0009(15)
C11 0.017(6) 0.0161(11) 0.013(3) 0.0023(9) 0.002(4) 0.0019(14)
C12 0.018(7) 0.0156(11) 0.014(3) 0.0012(9) 0.004(4) 0.0013(14)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.264(4) 3_656 ?
N1 C1 1.391(5) . ?
C1 C2 1.379(4) . ?
C1 C6 1.387(3) . ?
C2 C3 1.382(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.364(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.257(4) 3_757 ?
N2 C7 1.389(6) . ?
C7 C12 1.372(4) . ?
C7 C8 1.392(4) . ?
C8 C9 1.370(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.369(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.368(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 112.6(3) 3_656 . ?
C2 C1 C6 121.6(3) . . ?
C2 C1 N1 117.1(2) . . ?
C6 C1 N1 120.8(3) . . ?
C1 C2 C3 117.9(2) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 121.6(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 118.9(2) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2 N2 C7 112.4(4) 3_757 . ?
C12 C7 N2 115.7(3) . . ?
C12 C7 C8 121.9(4) . . ?
N2 C7 C8 121.9(3) . . ?
C9 C8 C7 119.3(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 118.6(2) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C9 C10 C11 121.8(3) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C7 117.9(3) . . ?
C11 C12 H12 121.0 . . ?
C7 C12 H12 121.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -170.7(6) 3_656 . . . ?
N1 N1 C1 C6 17.0(9) 3_656 . . . ?
C6 C1 C2 C3 0.1(10) . . . . ?
N1 C1 C2 C3 -172.2(5) . . . . ?
C1 C2 C3 C4 2.0(9) . . . . ?
C2 C3 C4 C5 -0.4(10) . . . . ?
C3 C4 C5 C6 -3.2(9) . . . . ?
C4 C5 C6 C1 5.2(9) . . . . ?
C2 C1 C6 C5 -3.7(10) . . . . ?
N1 C1 C6 C5 168.2(6) . . . . ?
N2 N2 C7 C12 170.7(6) 3_757 . . . ?
N2 N2 C7 C8 -17.1(9) 3_757 . . . ?
C12 C7 C8 C9 1.7(9) . . . . ?
N2 C7 C8 C9 -170.0(5) . . . . ?
C7 C8 C9 C10 -0.5(9) . . . . ?
C8 C9 C10 C11 -0.2(8) . . . . ?
C9 C10 C11 C12 -0.1(9) . . . . ?
C10 C11 C12 C7 1.2(9) . . . . ?
N2 C7 C12 C11 170.2(5) . . . . ?
C8 C7 C12 C11 -2.0(9) . . . . ?


_shelx_res_file                  
;
TITL sample_0157_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 17:39:42 on 21-Mar-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  11.834291   5.510022  10.478348  90.0000 116.1423  90.0000
ZERR    4.00   0.009849   0.000251   0.003813   0.0000   0.0749   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC N C H
DISP $C  0.00061  0.00098  7.16709!source kissel
DISP $H -0.00006  0.00048  5.12895!source kissel
DISP $N -0.00003  0.00000  0.64101!source kissel
UNIT 8 48 40
OMIT -3 -1 5
OMIT -3 1 5
OMIT 2 -1 0
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.03
FMAP 2
PLAN 20
WGHT    0.157200    0.025300
BASF   0.19034
FVAR      25.74023
N1    1    0.490598    0.110558    0.508289    11.00000    0.01650    0.01623 =
         0.01268   -0.00055    0.00328    0.00198
C1    2    0.421704    0.141964    0.585657    11.00000    0.01955    0.01481 =
         0.01317   -0.00019    0.00545    0.00066
C2    2    0.380167    0.373609    0.591822    11.00000    0.01299    0.01607 =
         0.01087    0.00005    0.00034    0.00042
AFIX  43
H2    3    0.388828    0.498276    0.536949    11.00000   -1.20000
AFIX   0
C3    2    0.325265    0.414558    0.682139    11.00000    0.02094    0.01553 =
         0.01371   -0.00025    0.00482    0.00106
AFIX  43
H3    3    0.294015    0.567621    0.686471    11.00000   -1.20000
AFIX   0
C4    2    0.316739    0.230378    0.765293    11.00000    0.01385    0.01757 =
         0.01381   -0.00003    0.00356    0.00121
AFIX  43
H4    3    0.280020    0.260960    0.825969    11.00000   -1.20000
AFIX   0
C5    2    0.361234    0.001105    0.761171    11.00000    0.01256    0.01628 =
         0.01339    0.00102    0.00047    0.00052
AFIX  43
H5    3    0.358611   -0.119921    0.821672    11.00000   -1.20000
AFIX   0
C6    2    0.409247   -0.045548    0.666815    11.00000    0.01697    0.01454 =
         0.01434   -0.00020    0.00339   -0.00028
AFIX  43
H6    3    0.433493   -0.202290    0.656979    11.00000   -1.20000
AFIX   0
N2    1    0.991434    0.109467    0.981220    11.00000    0.02177    0.01676 =
         0.01512    0.00220    0.00619    0.00214
C7    2    0.922136    0.136016    0.835202    11.00000    0.01085    0.01646 =
         0.01121    0.00188    0.00090    0.00142
C8    2    0.906464   -0.054215    0.741485    11.00000    0.01633    0.01467 =
         0.01500    0.00185    0.00311    0.00083
AFIX  43
H8    3    0.931252   -0.210689    0.775627    11.00000   -1.20000
AFIX   0
C9    2    0.854129   -0.008483    0.598402    11.00000    0.00829    0.01683 =
         0.01375   -0.00043   -0.00064   -0.00116
AFIX  43
H9    3    0.843442   -0.132693    0.533975    11.00000   -1.20000
AFIX   0
C10   2    0.817894    0.223829    0.552230    11.00000    0.01794    0.01768 =
         0.01586    0.00182    0.00494    0.00087
AFIX  43
H10   3    0.782572    0.256358    0.455267    11.00000   -1.20000
AFIX   0
C11   2    0.832274    0.410128    0.645168    11.00000    0.01652    0.01611 =
         0.01281    0.00229    0.00173    0.00188
AFIX  43
H11   3    0.806873    0.566143    0.610538    11.00000   -1.20000
AFIX   0
C12   2    0.883724    0.367809    0.788391    11.00000    0.01761    0.01558 =
         0.01434    0.00115    0.00354    0.00129
AFIX  43
H12   3    0.892382    0.492267    0.852005    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0157_bn1 in P2(1)/c
REM wR2 = 0.212963, GooF = S = 1.11549, Restrained GooF = 1.09859 for all data
REM R1 = 0.072216 for 2376 Fo > 4sig(Fo) and 0.078293 for all 2815 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.1568      0.0257

REM Highest difference peak  0.347,  deepest hole -0.440,  1-sigma level  0.090
Q1    1   0.8771  0.2431  0.7853  11.00000  0.05    0.35
Q2    1   0.3599  0.3242  0.7290  11.00000  0.05    0.34
Q3    1   0.7836  0.4810  0.6882  11.00000  0.05    0.34
Q4    1   0.3406  0.2536  0.5131  11.00000  0.05    0.33
Q5    1   0.8284  0.0994  0.5677  11.00000  0.05    0.32
Q6    1   0.9008  0.0336  0.9057  11.00000  0.05    0.29
Q7    1   0.4722  0.2536  0.6458  11.00000  0.05    0.29
Q8    1   0.9481  0.0519  0.7974  11.00000  0.05    0.29
Q9    1   0.9461  0.1245  0.8966  11.00000  0.05    0.28
Q10   1   0.8967  0.0457  0.7976  11.00000  0.05    0.28
Q11   1   0.5008  0.0102  0.5812  11.00000  0.05    0.28
Q12   1   0.3403 -0.0172  0.7061  11.00000  0.05    0.27
Q13   1   1.0507  0.2219  1.0385  11.00000  0.05    0.27
Q14   1   0.8156  0.3197  0.7192  11.00000  0.05    0.26
Q15   1   0.9799  0.2398  0.8783  11.00000  0.05    0.26
Q16   1   0.3404  0.4337  0.6337  11.00000  0.05    0.26
Q17   1   0.4979  0.1165  0.5539  11.00000  0.05    0.26
Q18   1   0.8140  0.3038  0.6060  11.00000  0.05    0.26
Q19   1   0.2477  0.0837  0.6763  11.00000  0.05    0.25
Q20   1   1.0211  0.0113  0.9325  11.00000  0.05    0.25
;
_shelx_res_checksum              47364
