# 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_20p6GPa
_database_code_depnum_ccdc_archive 'CCDC 2336592'
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_20p6GPa         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.332 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_20p6GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.65 Ang.  
RESPONSE: ...
;
_vrf_PLAT084_AZO_20p6GPa         
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.36 Report
RESPONSE: A large part of reciprocal space was shadowed by the pressure 
cell. 
;
_vrf_PLAT149_AZO_20p6GPa         
;
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_PLAT340_AZO_20p6GPa         
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01083 Ang.  
RESPONSE: A large part of reciprocal space was shadowed by the pressure 
cell.
;
_vrf_PLAT911_AZO_20p6GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        525 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                   11.789(11)
_cell_length_b                   5.5068(3)
_cell_length_c                   10.461(5)
_cell_angle_alpha                90
_cell_angle_beta                 116.23(9)
_cell_angle_gamma                90
_cell_volume                     609.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       20570000
_cell_measurement_reflns_used    469
_cell_measurement_theta_min      3.0960
_cell_measurement_theta_max      20.4080

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.987
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.11902
_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         20570000
_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      0.0386843161
_diffrn_orient_matrix_UB_12      0.0061299472
_diffrn_orient_matrix_UB_13      0.0214242884
_diffrn_orient_matrix_UB_21      -0.0029893533
_diffrn_orient_matrix_UB_22      0.0226852272
_diffrn_orient_matrix_UB_23      0.0356648114
_diffrn_orient_matrix_UB_31      0.0022884551
_diffrn_orient_matrix_UB_32      -0.0705619468
_diffrn_orient_matrix_UB_33      0.0132616392
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2583
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0254
_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         2.246
_diffrn_reflns_theta_max         21.566
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.208
_diffrn_measured_fraction_theta_full 0.332
_diffrn_reflns_Laue_measured_fraction_max 0.208
_diffrn_reflns_Laue_measured_fraction_full 0.332
_diffrn_reflns_point_group_measured_fraction_max 0.208
_diffrn_reflns_point_group_measured_fraction_full 0.332
_reflns_number_total             2583
_reflns_number_gt                1922
_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 25.8%. 
 A low-resolution reflection affected by beamstop [0 2 0] was removed from 
 refinement. Some other reflections were removed 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         2583
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.1457
_refine_ls_R_factor_gt           0.1256
_refine_ls_wR_factor_ref         0.3640
_refine_ls_wR_factor_gt          0.3305
_refine_ls_goodness_of_fit_ref   1.530
_refine_ls_restrained_S_all      1.511
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.103
_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 0.4914(9) 0.1104(6) 0.5090(7) 0.028(3) Uani 1 1 d . U . . .
C1 C 0.4229(11) 0.1416(8) 0.5868(8) 0.027(3) Uani 1 1 d . U . . .
C2 C 0.3800(11) 0.3737(7) 0.5924(8) 0.027(3) Uani 1 1 d . U . . .
H2 H 0.388031 0.498257 0.536847 0.032 Uiso 1 1 calc R U . . .
C3 C 0.3251(11) 0.4149(8) 0.6827(9) 0.028(3) Uani 1 1 d . U . . .
H3 H 0.293593 0.568000 0.686949 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3168(11) 0.2307(8) 0.7659(9) 0.028(3) Uani 1 1 d . U . . .
H4 H 0.280314 0.261377 0.827011 0.034 Uiso 1 1 calc R U . . .
C5 C 0.3611(11) 0.0011(8) 0.7616(9) 0.028(3) Uani 1 1 d . U . . .
H5 H 0.357993 -0.120049 0.821860 0.034 Uiso 1 1 calc R U . . .
C6 C 0.4097(11) -0.0462(8) 0.6679(8) 0.028(3) Uani 1 1 d . U . . .
H6 H 0.433782 -0.203291 0.658114 0.034 Uiso 1 1 calc R U . . .
N2 N 0.9912(9) 0.1095(6) 0.9808(7) 0.029(3) Uani 1 1 d . U . . .
C7 C 0.9238(11) 0.1365(8) 0.8362(8) 0.025(3) Uani 1 1 d . U . . .
C8 C 0.9056(11) -0.0529(9) 0.7410(9) 0.029(3) Uani 1 1 d . U . . .
H8 H 0.928386 -0.210490 0.774574 0.035 Uiso 1 1 calc R U . . .
C9 C 0.8545(11) -0.0071(8) 0.5984(8) 0.028(3) Uani 1 1 d . U . . .
H9 H 0.844985 -0.131249 0.534146 0.034 Uiso 1 1 calc R U . . .
C10 C 0.8170(11) 0.2259(8) 0.5511(9) 0.030(3) Uani 1 1 d . U . . .
H10 H 0.780535 0.258305 0.453811 0.037 Uiso 1 1 calc R U . . .
C11 C 0.8326(12) 0.4109(8) 0.6450(9) 0.028(3) Uani 1 1 d . U . . .
H11 H 0.808392 0.567663 0.610717 0.034 Uiso 1 1 calc R U . . .
C12 C 0.8830(11) 0.3687(8) 0.7874(9) 0.029(3) Uani 1 1 d . U . . .
H12 H 0.889846 0.493063 0.850589 0.034 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 0.024(8) 0.030(2) 0.029(4) -0.0001(15) 0.011(5) 0.002(2)
C1 0.025(8) 0.0298(19) 0.030(4) -0.0009(18) 0.014(5) 0.000(2)
C2 0.022(8) 0.027(2) 0.030(4) -0.0002(17) 0.010(6) -0.001(2)
C3 0.024(8) 0.030(2) 0.030(4) 0.0002(18) 0.011(6) 0.001(2)
C4 0.023(8) 0.031(2) 0.031(4) -0.0006(19) 0.013(6) 0.001(3)
C5 0.021(8) 0.030(2) 0.036(4) 0.001(2) 0.014(6) 0.001(3)
C6 0.026(8) 0.0281(19) 0.033(4) 0.0005(18) 0.014(5) 0.002(2)
N2 0.027(8) 0.028(2) 0.035(4) 0.0010(16) 0.016(5) 0.001(2)
C7 0.018(8) 0.030(2) 0.026(4) 0.0012(18) 0.008(6) 0.000(2)
C8 0.027(8) 0.0279(19) 0.033(4) 0.0013(19) 0.013(6) 0.000(3)
C9 0.022(9) 0.030(2) 0.033(4) 0.0004(19) 0.012(6) 0.000(3)
C10 0.028(9) 0.030(2) 0.035(4) -0.0015(19) 0.015(6) -0.004(3)
C11 0.025(8) 0.029(2) 0.030(4) 0.0011(18) 0.012(5) 0.001(2)
C12 0.025(8) 0.029(2) 0.033(4) 0.0007(18) 0.013(6) 0.001(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 1.260(7) 3_656 ?
N1 C1 1.388(8) . ?
C1 C2 1.385(7) . ?
C1 C6 1.389(7) . ?
C2 C3 1.380(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.361(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.259(8) 3_757 ?
N2 C7 1.370(11) . ?
C7 C12 1.382(8) . ?
C7 C8 1.392(8) . ?
C8 C9 1.363(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.376(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.358(11) . ?
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 112.3(6) 3_656 . ?
C2 C1 N1 117.2(4) . . ?
C2 C1 C6 121.3(5) . . ?
N1 C1 C6 121.1(5) . . ?
C3 C2 C1 118.1(5) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C4 C3 C2 120.1(5) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 121.7(5) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 119.1(4) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 119.6(5) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2 N2 C7 113.0(7) 3_757 . ?
N2 C7 C12 116.5(5) . . ?
N2 C7 C8 122.6(6) . . ?
C12 C7 C8 120.7(7) . . ?
C9 C8 C7 119.9(5) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 118.9(5) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C10 C9 121.0(7) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C10 121.0(6) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C7 118.4(5) . . ?
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 -169.3(11) 3_656 . . . ?
N1 N1 C1 C6 17.4(17) 3_656 . . . ?
N1 C1 C2 C3 -172.4(10) . . . . ?
C6 C1 C2 C3 0.9(17) . . . . ?
C1 C2 C3 C4 1.5(17) . . . . ?
C2 C3 C4 C5 -0.6(17) . . . . ?
C3 C4 C5 C6 -2.7(17) . . . . ?
C4 C5 C6 C1 5.1(16) . . . . ?
C2 C1 C6 C5 -4.3(17) . . . . ?
N1 C1 C6 C5 168.7(10) . . . . ?
N2 N2 C7 C12 170.0(9) 3_757 . . . ?
N2 N2 C7 C8 -15.3(15) 3_757 . . . ?
N2 C7 C8 C9 -170.2(9) . . . . ?
C12 C7 C8 C9 4.2(16) . . . . ?
C7 C8 C9 C10 -2.5(16) . . . . ?
C8 C9 C10 C11 1.2(15) . . . . ?
C9 C10 C11 C12 -1.5(16) . . . . ?
C10 C11 C12 C7 3.0(17) . . . . ?
N2 C7 C12 C11 170.4(9) . . . . ?
C8 C7 C12 C11 -4.4(16) . . . . ?


_shelx_res_file                  
;
TITL sample_0161_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 10:56:36 on 27-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  11.788554   5.506816  10.460597  90.0000 116.2270  90.0000
ZERR    4.00   0.011405   0.000289   0.004501   0.0000   0.0879   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 -3 -5 12
OMIT -3 -2 13
OMIT -6 6 11
OMIT 6 -6 -11
OMIT 5 -5 -10
OMIT 0 2 0
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.200000
BASF   0.25767
FVAR      25.86304
N1    1    0.491450    0.110386    0.508964    11.00000    0.02367    0.03008 =
         0.02864   -0.00013    0.01079    0.00221
C1    2    0.422893    0.141621    0.586797    11.00000    0.02505    0.02983 =
         0.03006   -0.00085    0.01444    0.00025
C2    2    0.380013    0.373742    0.592367    11.00000    0.02172    0.02730 =
         0.02967   -0.00015    0.01008   -0.00060
AFIX  43
H2    3    0.388031    0.498257    0.536847    11.00000   -1.20000
AFIX   0
C3    2    0.325051    0.414907    0.682678    11.00000    0.02358    0.03016 =
         0.03007    0.00022    0.01098    0.00125
AFIX  43
H3    3    0.293593    0.568000    0.686949    11.00000   -1.20000
AFIX   0
C4    2    0.316804    0.230705    0.765922    11.00000    0.02312    0.03113 =
         0.03121   -0.00055    0.01286    0.00132
AFIX  43
H4    3    0.280314    0.261377    0.827011    11.00000   -1.20000
AFIX   0
C5    2    0.361148    0.001083    0.761564    11.00000    0.02116    0.02951 =
         0.03593    0.00089    0.01395    0.00064
AFIX  43
H5    3    0.357993   -0.120049    0.821860    11.00000   -1.20000
AFIX   0
C6    2    0.409651   -0.046237    0.667851    11.00000    0.02599    0.02807 =
         0.03290    0.00052    0.01438    0.00193
AFIX  43
H6    3    0.433782   -0.203291    0.658114    11.00000   -1.20000
AFIX   0
N2    1    0.991151    0.109456    0.980764    11.00000    0.02742    0.02825 =
         0.03454    0.00103    0.01597    0.00064
C7    2    0.923833    0.136518    0.836233    11.00000    0.01807    0.03031 =
         0.02618    0.00121    0.00820    0.00048
C8    2    0.905640   -0.052946    0.740956    11.00000    0.02691    0.02793 =
         0.03317    0.00131    0.01324    0.00020
AFIX  43
H8    3    0.928386   -0.210490    0.774574    11.00000   -1.20000
AFIX   0
C9    2    0.854453   -0.007126    0.598383    11.00000    0.02174    0.02991 =
         0.03264    0.00037    0.01212    0.00013
AFIX  43
H9    3    0.844985   -0.131249    0.534146    11.00000   -1.20000
AFIX   0
C10   2    0.817009    0.225886    0.551053    11.00000    0.02824    0.02974 =
         0.03471   -0.00152    0.01509   -0.00374
AFIX  43
H10   3    0.780535    0.258305    0.453811    11.00000   -1.20000
AFIX   0
C11   2    0.832633    0.410900    0.644996    11.00000    0.02532    0.02921 =
         0.03001    0.00111    0.01170    0.00134
AFIX  43
H11   3    0.808392    0.567663    0.610717    11.00000   -1.20000
AFIX   0
C12   2    0.882999    0.368710    0.787424    11.00000    0.02477    0.02860 =
         0.03255    0.00072    0.01298    0.00105
AFIX  43
H12   3    0.889846    0.493063    0.850589    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0161_bn1 in P2(1)/c
REM wR2 = 0.3640, GooF = S = 1.530, Restrained GooF = 1.511 for all data
REM R1 = 0.1256 for 1922 Fo > 4sig(Fo) and 0.1457 for all 2583 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.2000      0.0000

REM Highest difference peak  0.431,  deepest hole -0.457,  1-sigma level  0.103
Q1    1   1.0014  0.0130  0.8101  11.00000  0.05    0.43
Q2    1   0.8085  0.4891  0.8504  11.00000  0.05    0.38
Q3    1   0.3992  0.3244  0.7558  11.00000  0.05    0.37
Q4    1   0.8980 -0.3046  0.8256  11.00000  0.05    0.36
Q5    1   0.8139  0.0715  0.5416  11.00000  0.05    0.35
Q6    1   0.9543  0.3001  0.8471  11.00000  0.05    0.35
Q7    1   0.3551  0.4073  0.6386  11.00000  0.05    0.35
Q8    1   0.8607  0.3242  0.6080  11.00000  0.05    0.34
Q9    1   0.4911  0.2867  0.4992  11.00000  0.05    0.34
Q10   1   0.3244  0.1408  0.7272  11.00000  0.05    0.34
Q11   1   0.8606  0.1953  0.7809  11.00000  0.05    0.34
Q12   1   0.2997 -0.1304  0.8500  11.00000  0.05    0.32
Q13   1   0.9905  0.2159  1.0161  11.00000  0.05    0.32
Q14   1   0.9007  0.1466  0.6060  11.00000  0.05    0.32
Q15   1   0.8982  0.0401  0.7838  11.00000  0.05    0.32
Q16   1   0.8435 -0.1834  0.5934  11.00000  0.05    0.31
Q17   1   0.7941 -0.1015  0.5404  11.00000  0.05    0.31
Q18   1   0.9317  0.4289  0.6476  11.00000  0.05    0.30
Q19   1   0.7378  0.1612  0.4898  11.00000  0.05    0.30
Q20   1   0.2484  0.5051  0.6079  11.00000  0.05    0.30
;
_shelx_res_checksum              21787
####################################################################### 
# 
# 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_21p2GPa
_database_code_depnum_ccdc_archive 'CCDC 2336593'
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_21p2GPa         
;
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_21p2GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.65 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_21p2GPa         
;
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_21p2GPa         
;
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                   11.750(9)
_cell_length_b                   5.5030(2)
_cell_length_c                   10.447(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.33(7)
_cell_angle_gamma                90
_cell_volume                     605.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       21240000
_cell_measurement_reflns_used    464
_cell_measurement_theta_min      2.2380
_cell_measurement_theta_max      20.4510

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.999
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.43240
_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         21240000
_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      -0.0388449841
_diffrn_orient_matrix_UB_12      0.0060618321
_diffrn_orient_matrix_UB_13      -0.0214891491
_diffrn_orient_matrix_UB_21      0.0029564459
_diffrn_orient_matrix_UB_22      0.0227494766
_diffrn_orient_matrix_UB_23      -0.0357247999
_diffrn_orient_matrix_UB_31      -0.0022694287
_diffrn_orient_matrix_UB_32      -0.0706068777
_diffrn_orient_matrix_UB_33      -0.0132941938
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2730
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0124
_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         2.249
_diffrn_reflns_theta_max         21.591
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.228
_diffrn_measured_fraction_theta_full 0.352
_diffrn_reflns_Laue_measured_fraction_max 0.228
_diffrn_reflns_Laue_measured_fraction_full 0.352
_diffrn_reflns_point_group_measured_fraction_max 0.228
_diffrn_reflns_point_group_measured_fraction_full 0.352
_reflns_number_total             2730
_reflns_number_gt                2256
_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 11%. 3 
 low-resolution reflections, that were affected by beamstop, were removed 
 from refinemet ( [-2 -1 0] [1 1 1] [-3 -1 1] ). Some other reflections were 
 removed 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)+(0.1801P)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         2730
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0757
_refine_ls_wR_factor_ref         0.2360
_refine_ls_wR_factor_gt          0.2277
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.112
_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 0.4912(6) 0.1109(3) 0.5086(4) 0.0153(18) Uani 1 1 d . U . . .
C1 C 0.4215(7) 0.1423(4) 0.5857(5) 0.0147(19) Uani 1 1 d . U . . .
C2 C 0.3800(7) 0.3742(4) 0.5923(4) 0.0138(19) Uani 1 1 d . U . . .
H2 H 0.388687 0.499281 0.537385 0.017 Uiso 1 1 calc R U . . .
C3 C 0.3252(7) 0.4146(4) 0.6831(5) 0.0160(19) Uani 1 1 d . U . . .
H3 H 0.293781 0.567865 0.687693 0.019 Uiso 1 1 calc R U . . .
C4 C 0.3168(7) 0.2303(5) 0.7664(5) 0.0154(19) Uani 1 1 d . U . . .
H4 H 0.280413 0.261136 0.827686 0.018 Uiso 1 1 calc R U . . .
C5 C 0.3608(6) 0.0003(4) 0.7618(4) 0.015(2) Uani 1 1 d . U . . .
H5 H 0.357655 -0.121370 0.821878 0.018 Uiso 1 1 calc R U . . .
C6 C 0.4093(7) -0.0456(4) 0.6671(5) 0.0151(19) Uani 1 1 d . U . . .
H6 H 0.434086 -0.202311 0.657320 0.018 Uiso 1 1 calc R U . . .
N2 N 0.9914(6) 0.1101(4) 0.9813(4) 0.0166(18) Uani 1 1 d . U . . .
C7 C 0.9217(7) 0.1375(4) 0.8349(4) 0.0137(19) Uani 1 1 d . U . . .
C8 C 0.9056(7) -0.0525(5) 0.7408(5) 0.017(2) Uani 1 1 d . U . . .
H8 H 0.930092 -0.209384 0.775092 0.021 Uiso 1 1 calc R U . . .
C9 C 0.8535(6) -0.0069(4) 0.5972(4) 0.016(2) Uani 1 1 d . U . . .
H9 H 0.842879 -0.131119 0.532554 0.019 Uiso 1 1 calc R U . . .
C10 C 0.8174(7) 0.2262(4) 0.5511(5) 0.017(2) Uani 1 1 d . U . . .
H10 H 0.781369 0.259062 0.453705 0.021 Uiso 1 1 calc R U . . .
C11 C 0.8329(7) 0.4123(4) 0.6447(5) 0.0157(19) Uani 1 1 d . U . . .
H11 H 0.808232 0.568879 0.609936 0.019 Uiso 1 1 calc R U . . .
C12 C 0.8845(7) 0.3702(4) 0.7887(5) 0.016(2) Uani 1 1 d . U . . .
H12 H 0.893819 0.494924 0.852753 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 0.013(6) 0.0154(11) 0.013(2) -0.0005(8) 0.002(3) 0.0023(13)
C1 0.013(6) 0.0152(10) 0.012(2) -0.0005(9) 0.002(4) -0.0002(14)
C2 0.009(6) 0.0155(11) 0.012(2) 0.0006(9) 0.000(4) 0.0009(14)
C3 0.017(6) 0.0143(11) 0.013(2) 0.0004(9) 0.002(4) 0.0022(15)
C4 0.012(6) 0.0172(11) 0.014(2) -0.0001(10) 0.003(4) 0.0012(15)
C5 0.010(6) 0.0162(12) 0.015(2) 0.0013(10) 0.001(4) 0.0012(15)
C6 0.012(6) 0.0138(10) 0.014(2) 0.0004(9) 0.002(4) 0.0011(15)
N2 0.016(6) 0.0157(11) 0.016(2) 0.0016(9) 0.005(3) 0.0015(13)
C7 0.009(6) 0.0161(11) 0.012(2) 0.0021(9) 0.001(4) 0.0018(14)
C8 0.018(6) 0.0138(10) 0.018(3) 0.0018(10) 0.006(4) 0.0011(15)
C9 0.011(6) 0.0161(11) 0.015(3) -0.0004(10) 0.002(4) -0.0011(15)
C10 0.017(6) 0.0171(11) 0.016(2) 0.0012(10) 0.005(4) 0.0004(16)
C11 0.013(6) 0.0148(11) 0.014(2) 0.0022(10) 0.001(4) 0.0023(15)
C12 0.014(6) 0.0154(12) 0.015(3) 0.0010(10) 0.003(4) 0.0011(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 1.264(4) 3_656 ?
N1 C1 1.391(5) . ?
C1 C2 1.378(4) . ?
C1 C6 1.386(4) . ?
C2 C3 1.381(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.366(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.261(4) 3_757 ?
N2 C7 1.386(6) . ?
C7 C12 1.370(4) . ?
C7 C8 1.390(4) . ?
C8 C9 1.369(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.370(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.371(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 112.3(3) 3_656 . ?
C2 C1 C6 121.7(3) . . ?
C2 C1 N1 117.1(2) . . ?
C6 C1 N1 120.6(3) . . ?
C1 C2 C3 117.8(2) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 121.7(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 118.7(2) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
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 115.5(3) . . ?
C12 C7 C8 122.1(4) . . ?
N2 C7 C8 121.8(4) . . ?
C9 C8 C7 119.5(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 118.4(3) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C9 C10 C11 121.7(4) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C7 117.5(3) . . ?
C11 C12 H12 121.3 . . ?
C7 C12 H12 121.3 . . ?

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(7) 3_656 . . . ?
N1 N1 C1 C6 17.8(10) 3_656 . . . ?
C6 C1 C2 C3 -0.1(10) . . . . ?
N1 C1 C2 C3 -171.8(6) . . . . ?
C1 C2 C3 C4 2.1(10) . . . . ?
C2 C3 C4 C5 -0.7(10) . . . . ?
C3 C4 C5 C6 -2.7(10) . . . . ?
C4 C5 C6 C1 4.5(10) . . . . ?
C2 C1 C6 C5 -3.2(10) . . . . ?
N1 C1 C6 C5 168.2(6) . . . . ?
N2 N2 C7 C12 171.4(6) 3_757 . . . ?
N2 N2 C7 C8 -16.9(9) 3_757 . . . ?
C12 C7 C8 C9 1.4(10) . . . . ?
N2 C7 C8 C9 -169.8(6) . . . . ?
C7 C8 C9 C10 -0.8(9) . . . . ?
C8 C9 C10 C11 0.4(9) . . . . ?
C9 C10 C11 C12 -0.7(9) . . . . ?
C10 C11 C12 C7 1.3(10) . . . . ?
N2 C7 C12 C11 170.1(6) . . . . ?
C8 C7 C12 C11 -1.6(10) . . . . ?


_shelx_res_file                  
;
TITL sample_0163_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 11:00:53 on 27-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  11.750369   5.502999  10.447178  90.0000 116.3339  90.0000
ZERR    4.00   0.009004   0.000237   0.003528   0.0000   0.0694   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 2 2
OMIT -2 -1 0
OMIT 3 1 -5
OMIT 3 -1 -5
OMIT 1 1 1
OMIT -3 -1 1
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.180100
BASF   0.11022
FVAR      24.93165
N1    1    0.491155    0.110877    0.508644    11.00000    0.01320    0.01542 =
         0.01314   -0.00050    0.00206    0.00234
C1    2    0.421455    0.142307    0.585745    11.00000    0.01307    0.01516 =
         0.01213   -0.00051    0.00230   -0.00019
C2    2    0.380011    0.374220    0.592287    11.00000    0.00882    0.01553 =
         0.01225    0.00059    0.00020    0.00092
AFIX  43
H2    3    0.388687    0.499281    0.537385    11.00000   -1.20000
AFIX   0
C3    2    0.325164    0.414639    0.683117    11.00000    0.01676    0.01431 =
         0.01255    0.00036    0.00241    0.00220
AFIX  43
H3    3    0.293781    0.567865    0.687693    11.00000   -1.20000
AFIX   0
C4    2    0.316803    0.230258    0.766380    11.00000    0.01185    0.01718 =
         0.01443   -0.00011    0.00330    0.00115
AFIX  43
H4    3    0.280413    0.261136    0.827686    11.00000   -1.20000
AFIX   0
C5    2    0.360837    0.000310    0.761772    11.00000    0.00988    0.01616 =
         0.01465    0.00135    0.00107    0.00125
AFIX  43
H5    3    0.357655   -0.121370    0.821878    11.00000   -1.20000
AFIX   0
C6    2    0.409330   -0.045626    0.667104    11.00000    0.01217    0.01378 =
         0.01441    0.00040    0.00154    0.00108
AFIX  43
H6    3    0.434086   -0.202311    0.657320    11.00000   -1.20000
AFIX   0
N2    1    0.991413    0.110066    0.981320    11.00000    0.01612    0.01571 =
         0.01567    0.00156    0.00487    0.00151
C7    2    0.921696    0.137477    0.834937    11.00000    0.00882    0.01608 =
         0.01205    0.00206    0.00085    0.00185
C8    2    0.905629   -0.052503    0.740806    11.00000    0.01846    0.01379 =
         0.01782    0.00184    0.00586    0.00108
AFIX  43
H8    3    0.930092   -0.209384    0.775092    11.00000   -1.20000
AFIX   0
C9    2    0.853513   -0.006860    0.597236    11.00000    0.01055    0.01611 =
         0.01534   -0.00043    0.00161   -0.00112
AFIX  43
H9    3    0.842879   -0.131119    0.532554    11.00000   -1.20000
AFIX   0
C10   2    0.817394    0.226196    0.551090    11.00000    0.01656    0.01705 =
         0.01611    0.00118    0.00482    0.00040
AFIX  43
H10   3    0.781369    0.259062    0.453705    11.00000   -1.20000
AFIX   0
C11   2    0.832940    0.412296    0.644652    11.00000    0.01282    0.01479 =
         0.01407    0.00217    0.00114    0.00228
AFIX  43
H11   3    0.808232    0.568879    0.609936    11.00000   -1.20000
AFIX   0
C12   2    0.884468    0.370235    0.788743    11.00000    0.01374    0.01539 =
         0.01531    0.00095    0.00311    0.00113
AFIX  43
H12   3    0.893819    0.494924    0.852753    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0163_bn1 in P2(1)/c
REM wR2 = 0.2360, GooF = S = 1.122, Restrained GooF = 1.109 for all data
REM R1 = 0.0757 for 2256 Fo > 4sig(Fo) and 0.0824 for all 2730 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.1801      0.0000

REM Highest difference peak  0.560,  deepest hole -0.483,  1-sigma level  0.112
Q1    1   0.4634  0.1260  0.5515  11.00000  0.05    0.56
Q2    1   0.8645  0.3847  0.7277  11.00000  0.05    0.53
Q3    1   0.3400  0.3983  0.6353  11.00000  0.05    0.53
Q4    1   0.3585 -0.0177  0.7053  11.00000  0.05    0.51
Q5    1   0.8854 -0.0455  0.6782  11.00000  0.05    0.49
Q6    1   0.9614  0.1212  0.9024  11.00000  0.05    0.45
Q7    1   0.8361  0.3718  0.5973  11.00000  0.05    0.38
Q8    1   0.4483  0.2541  0.6240  11.00000  0.05    0.34
Q9    1   0.8679  0.2436  0.7861  11.00000  0.05    0.33
Q10   1   0.2969  0.2873  0.7052  11.00000  0.05    0.32
Q11   1   0.8151 -0.0781  0.7747  11.00000  0.05    0.32
Q12   1   0.4846 -0.3230  0.7788  11.00000  0.05    0.30
Q13   1   1.0582  0.2152  1.0418  11.00000  0.05    0.30
Q14   1   0.2217  0.1572  0.6581  11.00000  0.05    0.30
Q15   1   0.7084  0.1179  0.4600  11.00000  0.05    0.30
Q16   1   0.7144  0.1991  0.6021  11.00000  0.05    0.29
Q17   1   0.4294  0.4650  0.8281  11.00000  0.05    0.29
Q18   1   1.0348  0.1268  0.8203  11.00000  0.05    0.29
Q19   1   0.2525  0.1127  0.7134  11.00000  0.05    0.29
Q20   1   0.8381 -0.2221  0.4161  11.00000  0.05    0.28
;
_shelx_res_checksum              5693
####################################################################### 
# 
# 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_25p9GPa
_database_code_depnum_ccdc_archive 'CCDC 2336602'
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_25p9GPa         
;
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_PLAT411_AZO_25p9GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.61 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_25p9GPa         
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.17 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_25p9GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        509 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             2023-03-17
_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                   11.47(2)
_cell_length_b                   5.4795(5)
_cell_length_c                   10.352(8)
_cell_angle_alpha                90
_cell_angle_beta                 116.77(17)
_cell_angle_gamma                90
_cell_volume                     580.7(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       25890000
_cell_measurement_reflns_used    451
_cell_measurement_theta_min      3.1160
_cell_measurement_theta_max      20.6170

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.084
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.47673
_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         25890000
_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    2.00    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0400099764
_diffrn_orient_matrix_UB_12      0.0053284572
_diffrn_orient_matrix_UB_13      -0.0219298654
_diffrn_orient_matrix_UB_21      0.0027435967
_diffrn_orient_matrix_UB_22      0.0235443787
_diffrn_orient_matrix_UB_23      -0.0360927004
_diffrn_orient_matrix_UB_31      -0.0018583118
_diffrn_orient_matrix_UB_32      -0.0707175749
_diffrn_orient_matrix_UB_33      -0.0134912968
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2488
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_av_R_equivalents  0.0100
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_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         2.270
_diffrn_reflns_theta_max         21.752
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.220
_diffrn_measured_fraction_theta_full 0.337
_diffrn_reflns_Laue_measured_fraction_max 0.220
_diffrn_reflns_Laue_measured_fraction_full 0.337
_diffrn_reflns_point_group_measured_fraction_max 0.220
_diffrn_reflns_point_group_measured_fraction_full 0.337
_reflns_number_total             2488
_reflns_number_gt                2015
_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 9.8%. 
 2 low-resolution reflections, that were affected by beamstop, were removed 
 from refinemet ( [-1 1 -1] [2 -1 0] ). Some other reflections were removed 
 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)+(0.1536P)²+0.0677P] 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         2488
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0754
_refine_ls_wR_factor_ref         0.2448
_refine_ls_wR_factor_gt          0.2348
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_restrained_S_all      1.174
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.690
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.106
_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(7) 0.1112(4) 0.5086(5) 0.0206(18) Uani 1 1 d . U . . .
C1 C 0.4213(9) 0.1431(5) 0.5866(6) 0.0207(18) Uani 1 1 d . U . . .
C2 C 0.3793(9) 0.3754(5) 0.5937(6) 0.0194(18) Uani 1 1 d . U . . .
H2 H 0.387248 0.501113 0.537864 0.023 Uiso 1 1 calc R U . . .
C3 C 0.3249(9) 0.4154(5) 0.6864(6) 0.0217(19) Uani 1 1 d . U . . .
H3 H 0.294381 0.569942 0.692762 0.026 Uiso 1 1 calc R U . . .
C4 C 0.3157(9) 0.2291(6) 0.7692(6) 0.0220(19) Uani 1 1 d . U . . .
H4 H 0.279683 0.260198 0.832082 0.026 Uiso 1 1 calc R U . . .
C5 C 0.3580(9) -0.0018(5) 0.7623(6) 0.0222(19) Uani 1 1 d . U . . .
H5 H 0.353401 -0.125034 0.821600 0.027 Uiso 1 1 calc R U . . .
C6 C 0.4068(9) -0.0474(5) 0.6667(6) 0.0208(18) Uani 1 1 d . U . . .
H6 H 0.430397 -0.205291 0.655116 0.025 Uiso 1 1 calc R U . . .
N2 N 0.9915(7) 0.1113(4) 0.9824(5) 0.0216(18) Uani 1 1 d . U . . .
C7 C 0.9212(9) 0.1431(6) 0.8349(6) 0.0212(18) Uani 1 1 d . U . . .
C8 C 0.9042(9) -0.0461(6) 0.7393(6) 0.0234(19) Uani 1 1 d . U . . .
H8 H 0.928242 -0.204088 0.774015 0.028 Uiso 1 1 calc R U . . .
C9 C 0.8521(9) -0.0011(5) 0.5941(6) 0.0229(19) Uani 1 1 d . U . . .
H9 H 0.839913 -0.126025 0.528450 0.027 Uiso 1 1 calc R U . . .
C10 C 0.8185(9) 0.2339(5) 0.5489(6) 0.0239(19) Uani 1 1 d . U . . .
H10 H 0.782476 0.268024 0.450494 0.029 Uiso 1 1 calc R U . . .
C11 C 0.8362(9) 0.4209(6) 0.6434(6) 0.0234(19) Uani 1 1 d . U . . .
H11 H 0.814323 0.579153 0.608352 0.028 Uiso 1 1 calc R U . . .
C12 C 0.8854(9) 0.3784(5) 0.7888(6) 0.0215(19) Uani 1 1 d . U . . .
H12 H 0.894271 0.503340 0.853451 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 0.017(5) 0.0196(12) 0.019(2) 0.0000(10) 0.002(3) 0.0032(16)
C1 0.020(6) 0.0186(11) 0.017(2) 0.0006(12) 0.003(3) 0.0014(18)
C2 0.014(6) 0.0196(12) 0.018(2) 0.0010(11) 0.001(3) 0.0010(17)
C3 0.022(6) 0.0180(12) 0.019(3) 0.0007(11) 0.004(3) 0.0021(18)
C4 0.020(6) 0.0210(12) 0.019(3) 0.0003(12) 0.004(4) 0.0005(18)
C5 0.020(6) 0.0199(13) 0.020(2) 0.0013(12) 0.003(3) 0.0012(18)
C6 0.018(6) 0.0183(11) 0.019(2) -0.0004(12) 0.002(3) -0.0002(18)
N2 0.019(5) 0.0198(12) 0.020(2) 0.0033(10) 0.004(3) 0.0024(16)
C7 0.017(6) 0.0218(12) 0.020(3) 0.0036(12) 0.005(3) 0.0018(18)
C8 0.024(6) 0.0205(12) 0.023(3) 0.0030(12) 0.007(4) 0.0021(19)
C9 0.020(6) 0.0221(13) 0.019(3) 0.0017(12) 0.002(4) 0.0025(18)
C10 0.022(6) 0.0236(13) 0.021(3) 0.0006(12) 0.005(4) 0.0024(19)
C11 0.023(6) 0.0219(12) 0.019(3) 0.0031(12) 0.004(4) 0.0047(19)
C12 0.017(6) 0.0211(13) 0.021(3) 0.0028(12) 0.004(4) 0.0032(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 1.263(5) 3_656 ?
N1 C1 1.379(7) . ?
C1 C2 1.374(5) . ?
C1 C6 1.389(4) . ?
C2 C3 1.377(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.362(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.263(5) 3_757 ?
N2 C7 1.380(8) . ?
C7 C12 1.372(5) . ?
C7 C8 1.385(5) . ?
C8 C9 1.367(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.365(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.367(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(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 112.4(4) 3_656 . ?
C2 C1 N1 117.3(3) . . ?
C2 C1 C6 121.7(4) . . ?
N1 C1 C6 120.7(4) . . ?
C1 C2 C3 117.6(3) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 121.9(4) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 118.6(3) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2 N2 C7 112.3(5) 3_757 . ?
C12 C7 N2 115.9(4) . . ?
C12 C7 C8 122.1(5) . . ?
N2 C7 C8 121.4(4) . . ?
C9 C8 C7 120.1(4) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 117.6(3) . . ?
C10 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
C9 C10 C11 122.3(5) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
C10 C11 C12 121.0(4) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C7 116.9(3) . . ?
C11 C12 H12 121.6 . . ?
C7 C12 H12 121.6 . . ?

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 -170.7(9) 3_656 . . . ?
N1 N1 C1 C6 15.9(13) 3_656 . . . ?
N1 C1 C2 C3 -171.6(7) . . . . ?
C6 C1 C2 C3 1.7(13) . . . . ?
C1 C2 C3 C4 0.9(13) . . . . ?
C2 C3 C4 C5 -0.8(13) . . . . ?
C3 C4 C5 C6 -2.0(13) . . . . ?
C4 C5 C6 C1 4.5(12) . . . . ?
C2 C1 C6 C5 -4.5(13) . . . . ?
N1 C1 C6 C5 168.6(8) . . . . ?
N2 N2 C7 C12 172.8(8) 3_757 . . . ?
N2 N2 C7 C8 -15.8(11) 3_757 . . . ?
C12 C7 C8 C9 1.0(13) . . . . ?
N2 C7 C8 C9 -169.8(7) . . . . ?
C7 C8 C9 C10 0.1(12) . . . . ?
C8 C9 C10 C11 0.4(13) . . . . ?
C9 C10 C11 C12 -1.9(14) . . . . ?
C10 C11 C12 C7 2.8(13) . . . . ?
N2 C7 C12 C11 168.9(7) . . . . ?
C8 C7 C12 C11 -2.4(12) . . . . ?


_shelx_res_file                  
;
TITL sample_0186_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 17:27:32 on 28-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  11.466900   5.479541  10.352229  90.0000 116.7738  90.0000
ZERR    4.00   0.021577   0.000522   0.008361   0.0000   0.1696   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 -3 -1
OMIT 2 -2 2
OMIT 2 -2 2
OMIT 4 -2 -1
OMIT -1 1 -1
OMIT 2 -1 0
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.003
FMAP 2
PLAN 20
WGHT    0.153600    0.067700
BASF   0.09831
FVAR      25.39426
N1    1    0.490869    0.111210    0.508614    11.00000    0.01691    0.01959 =
         0.01870    0.00005    0.00225    0.00316
C1    2    0.421258    0.143147    0.586642    11.00000    0.02026    0.01862 =
         0.01734    0.00057    0.00320    0.00145
C2    2    0.379261    0.375410    0.593721    11.00000    0.01375    0.01961 =
         0.01779    0.00097    0.00082    0.00098
AFIX  43
H2    3    0.387248    0.501113    0.537864    11.00000   -1.20000
AFIX   0
C3    2    0.324948    0.415410    0.686423    11.00000    0.02188    0.01795 =
         0.01927    0.00065    0.00401    0.00210
AFIX  43
H3    3    0.294381    0.569942    0.692762    11.00000   -1.20000
AFIX   0
C4    2    0.315707    0.229077    0.769249    11.00000    0.02041    0.02100 =
         0.01939    0.00030    0.00423    0.00053
AFIX  43
H4    3    0.279683    0.260198    0.832082    11.00000   -1.20000
AFIX   0
C5    2    0.357956   -0.001773    0.762282    11.00000    0.02037    0.01992 =
         0.01951    0.00133    0.00284    0.00121
AFIX  43
H5    3    0.353401   -0.125034    0.821600    11.00000   -1.20000
AFIX   0
C6    2    0.406831   -0.047421    0.666693    11.00000    0.01767    0.01830 =
         0.01944   -0.00044    0.00227   -0.00020
AFIX  43
H6    3    0.430397   -0.205291    0.655116    11.00000   -1.20000
AFIX   0
N2    1    0.991458    0.111324    0.982389    11.00000    0.01893    0.01976 =
         0.02031    0.00333    0.00363    0.00241
C7    2    0.921208    0.143071    0.834866    11.00000    0.01721    0.02181 =
         0.02021    0.00360    0.00469    0.00183
C8    2    0.904190   -0.046128    0.739339    11.00000    0.02387    0.02046 =
         0.02253    0.00299    0.00745    0.00210
AFIX  43
H8    3    0.928242   -0.204088    0.774015    11.00000   -1.20000
AFIX   0
C9    2    0.852075   -0.001052    0.594101    11.00000    0.01990    0.02209 =
         0.01930    0.00165    0.00228    0.00247
AFIX  43
H9    3    0.839913   -0.126025    0.528450    11.00000   -1.20000
AFIX   0
C10   2    0.818548    0.233901    0.548940    11.00000    0.02238    0.02362 =
         0.02059    0.00063    0.00503    0.00240
AFIX  43
H10   3    0.782476    0.268024    0.450494    11.00000   -1.20000
AFIX   0
C11   2    0.836151    0.420854    0.643407    11.00000    0.02320    0.02185 =
         0.01921    0.00306    0.00441    0.00469
AFIX  43
H11   3    0.814323    0.579153    0.608352    11.00000   -1.20000
AFIX   0
C12   2    0.885440    0.378445    0.788845    11.00000    0.01747    0.02112 =
         0.02053    0.00280    0.00379    0.00315
AFIX  43
H12   3    0.894271    0.503340    0.853451    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0186_bn1 in P2(1)/c
REM wR2 = 0.2448, GooF = S = 1.170, Restrained GooF = 1.174 for all data
REM R1 = 0.0754 for 2015 Fo > 4sig(Fo) and 0.0837 for all 2488 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.1536      0.0677

REM Highest difference peak  0.690,  deepest hole -0.380,  1-sigma level  0.106
Q1    1   0.3477  0.3790  0.6316  11.00000  0.05    0.69
Q2    1   0.3594 -0.0257  0.7086  11.00000  0.05    0.59
Q3    1   0.4625  0.1194  0.5498  11.00000  0.05    0.54
Q4    1   0.8618 -0.0137  0.6570  11.00000  0.05    0.52
Q5    1   0.8677  0.4054  0.7260  11.00000  0.05    0.45
Q6    1   0.9516  0.1353  0.9049  11.00000  0.05    0.45
Q7    1   0.9357  0.4762  0.8343  11.00000  0.05    0.44
Q8    1   0.4091 -0.0028  0.4345  11.00000  0.05    0.38
Q9    1   0.9518  0.0424  0.7742  11.00000  0.05    0.37
Q10   1   0.9310  0.1197  0.9878  11.00000  0.05    0.34
Q11   1   0.7823  0.0867  0.5522  11.00000  0.05    0.32
Q12   1   0.8960  0.2901  0.5709  11.00000  0.05    0.31
Q13   1   0.3990  0.1216  0.8174  11.00000  0.05    0.31
Q14   1   0.4713  0.0429  0.6971  11.00000  0.05    0.31
Q15   1   0.3020  0.2629  0.7094  11.00000  0.05    0.31
Q16   1   0.4044  0.5057  0.7599  11.00000  0.05    0.30
Q17   1   0.8483  0.2420  0.7781  11.00000  0.05    0.28
Q18   1   0.2518  0.3746  0.7092  11.00000  0.05    0.28
Q19   1   0.4262  0.2716  0.6222  11.00000  0.05    0.27
Q20   1   0.9300  0.4795  0.6701  11.00000  0.05    0.27
;
_shelx_res_checksum              87244
####################################################################### 
# 
# 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_23p6GPa
_database_code_depnum_ccdc_archive 'CCDC 2336598'
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_23p6GPa         
;
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_23p6GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.62 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_23p6GPa         
;
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_23p6GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        505 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             2023-03-17
_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                   11.626(10)
_cell_length_b                   5.4869(2)
_cell_length_c                   10.397(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.56(8)
_cell_angle_gamma                90
_cell_volume                     593.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       23570000
_cell_measurement_reflns_used    482
_cell_measurement_theta_min      2.2550
_cell_measurement_theta_max      20.5360

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.040
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.35573
_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         23570000
_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      -0.0393675824
_diffrn_orient_matrix_UB_12      0.0056446670
_diffrn_orient_matrix_UB_13      -0.0216572403
_diffrn_orient_matrix_UB_21      0.0027949268
_diffrn_orient_matrix_UB_22      0.0230911125
_diffrn_orient_matrix_UB_23      -0.0359525054
_diffrn_orient_matrix_UB_31      -0.0021262854
_diffrn_orient_matrix_UB_32      -0.0707485640
_diffrn_orient_matrix_UB_33      -0.0134040638
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2737
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0114
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_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         2.260
_diffrn_reflns_theta_max         21.685
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.225
_diffrn_measured_fraction_theta_full 0.344
_diffrn_reflns_Laue_measured_fraction_max 0.225
_diffrn_reflns_Laue_measured_fraction_full 0.344
_diffrn_reflns_point_group_measured_fraction_max 0.225
_diffrn_reflns_point_group_measured_fraction_full 0.344
_reflns_number_total             2737
_reflns_number_gt                2268
_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 14%. 2 
 low-resolution reflections, that were affected by beamstop, were removed 
 from refinemet ( [2 -1 0] [-1 1 -1] ). Some other reflections were removed 
 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)+(0.1660P)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         2737
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_ref         0.2140
_refine_ls_wR_factor_gt          0.2057
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.104
_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 0.4912(5) 0.1112(3) 0.5087(4) 0.0148(17) Uani 1 1 d . U . . .
C1 C 0.4207(6) 0.1428(4) 0.5857(5) 0.0145(17) Uani 1 1 d . U . . .
C2 C 0.3796(6) 0.3755(4) 0.5930(4) 0.0145(18) Uani 1 1 d . U . . .
H2 H 0.388373 0.501148 0.538008 0.017 Uiso 1 1 calc R U . . .
C3 C 0.3250(6) 0.4156(4) 0.6848(4) 0.0167(18) Uani 1 1 d . U . . .
H3 H 0.293548 0.569227 0.689992 0.020 Uiso 1 1 calc R U . . .
C4 C 0.3171(6) 0.2299(4) 0.7681(4) 0.0163(17) Uani 1 1 d . U . . .
H4 H 0.281388 0.260838 0.830586 0.020 Uiso 1 1 calc R U . . .
C5 C 0.3603(6) -0.0008(4) 0.7624(4) 0.0163(18) Uani 1 1 d . U . . .
H5 H 0.356899 -0.123255 0.822465 0.020 Uiso 1 1 calc R U . . .
C6 C 0.4083(6) -0.0463(4) 0.6670(4) 0.0154(17) Uani 1 1 d . U . . .
H6 H 0.432706 -0.203540 0.656412 0.018 Uiso 1 1 calc R U . . .
N2 N 0.9920(5) 0.1108(3) 0.9818(4) 0.0167(17) Uani 1 1 d . U . . .
C7 C 0.9217(6) 0.1397(4) 0.8348(4) 0.0140(17) Uani 1 1 d . U . . .
C8 C 0.9048(6) -0.0504(4) 0.7398(4) 0.0171(18) Uani 1 1 d . U . . .
H8 H 0.929060 -0.207972 0.774275 0.020 Uiso 1 1 calc R U . . .
C9 C 0.8524(6) -0.0048(4) 0.5955(4) 0.0151(18) Uani 1 1 d . U . . .
H9 H 0.840504 -0.129622 0.530195 0.018 Uiso 1 1 calc R U . . .
C10 C 0.8179(6) 0.2296(4) 0.5499(4) 0.0170(18) Uani 1 1 d . U . . .
H10 H 0.782848 0.263394 0.452044 0.020 Uiso 1 1 calc R U . . .
C11 C 0.8334(6) 0.4160(4) 0.6436(4) 0.0158(17) Uani 1 1 d . U . . .
H11 H 0.808796 0.573114 0.608563 0.019 Uiso 1 1 calc R U . . .
C12 C 0.8849(6) 0.3736(4) 0.7885(4) 0.0166(19) Uani 1 1 d . U . . .
H12 H 0.894445 0.498601 0.852925 0.020 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) 0.0132(10) 0.013(2) -0.0001(8) 0.003(3) 0.0027(12)
C1 0.016(5) 0.0124(9) 0.013(2) -0.0004(9) 0.005(3) 0.0000(13)
C2 0.013(6) 0.0129(10) 0.013(2) 0.0003(9) 0.003(4) 0.0005(13)
C3 0.021(6) 0.0118(10) 0.015(2) -0.0003(9) 0.005(3) 0.0013(14)
C4 0.018(6) 0.0141(10) 0.016(2) 0.0007(9) 0.007(3) 0.0019(14)
C5 0.017(6) 0.0132(11) 0.016(2) 0.0011(9) 0.005(4) 0.0007(14)
C6 0.016(5) 0.0123(10) 0.015(2) 0.0001(9) 0.004(3) 0.0002(14)
N2 0.019(5) 0.0139(11) 0.017(2) 0.0025(8) 0.008(3) 0.0028(12)
C7 0.013(5) 0.0130(10) 0.014(2) 0.0018(9) 0.004(3) 0.0010(13)
C8 0.020(6) 0.0120(10) 0.018(2) 0.0013(9) 0.008(4) 0.0001(14)
C9 0.012(6) 0.0137(11) 0.015(2) -0.0002(9) 0.003(4) -0.0002(14)
C10 0.018(6) 0.0143(11) 0.017(2) 0.0007(10) 0.007(3) 0.0002(14)
C11 0.017(5) 0.0124(10) 0.015(2) 0.0009(9) 0.004(3) 0.0011(14)
C12 0.019(6) 0.0130(11) 0.017(2) 0.0015(9) 0.006(4) 0.0020(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 1.388(5) . ?
C1 C2 1.377(4) . ?
C1 C6 1.386(3) . ?
C2 C3 1.380(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.361(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.263(4) 3_757 ?
N2 C7 1.383(6) . ?
C7 C12 1.370(4) . ?
C7 C8 1.388(4) . ?
C8 C9 1.367(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.367(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 112.3(3) 3_656 . ?
C2 C1 C6 121.8(3) . . ?
C2 C1 N1 117.1(2) . . ?
C6 C1 N1 120.5(3) . . ?
C1 C2 C3 117.7(2) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 122.1(3) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 118.5(2) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N2 N2 C7 112.1(4) 3_757 . ?
C12 C7 N2 115.6(3) . . ?
C12 C7 C8 122.1(4) . . ?
N2 C7 C8 121.7(3) . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 118.1(3) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 H9 121.0 . . ?
C11 C10 C9 122.1(3) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C10 C11 C12 120.7(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 117.4(3) . . ?
C11 C12 H12 121.3 . . ?
C7 C12 H12 121.3 . . ?

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 -170.8(6) 3_656 . . . ?
N1 N1 C1 C6 17.8(9) 3_656 . . . ?
C6 C1 C2 C3 0.0(10) . . . . ?
N1 C1 C2 C3 -171.3(5) . . . . ?
C1 C2 C3 C4 2.2(9) . . . . ?
C2 C3 C4 C5 -1.1(9) . . . . ?
C3 C4 C5 C6 -2.3(9) . . . . ?
C4 C5 C6 C1 4.4(9) . . . . ?
C2 C1 C6 C5 -3.3(10) . . . . ?
N1 C1 C6 C5 167.7(6) . . . . ?
N2 N2 C7 C12 171.3(5) 3_757 . . . ?
N2 N2 C7 C8 -17.0(8) 3_757 . . . ?
C12 C7 C8 C9 1.4(9) . . . . ?
N2 C7 C8 C9 -169.8(5) . . . . ?
C7 C8 C9 C10 -0.2(8) . . . . ?
C8 C9 C10 C11 -0.5(8) . . . . ?
C9 C10 C11 C12 0.1(9) . . . . ?
C10 C11 C12 C7 1.1(9) . . . . ?
N2 C7 C12 C11 169.8(5) . . . . ?
C8 C7 C12 C11 -1.9(9) . . . . ?


_shelx_res_file                  
;
TITL sample_0173_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 16:32:09 on 28-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  11.625756   5.486858  10.396867  90.0000 116.5595  90.0000
ZERR    4.00   0.009878   0.000242   0.004018   0.0000   0.0784   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 5
OMIT -3 1 5
OMIT -1 1 -1
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.166000
BASF   0.14027
FVAR      25.28855
N1    1    0.491158    0.111175    0.508722    11.00000    0.01426    0.01321 =
         0.01330   -0.00008    0.00286    0.00271
C1    2    0.420661    0.142758    0.585656    11.00000    0.01580    0.01239 =
         0.01339   -0.00044    0.00473   -0.00002
C2    2    0.379610    0.375460    0.592996    11.00000    0.01334    0.01295 =
         0.01338    0.00027    0.00263    0.00054
AFIX  43
H2    3    0.388373    0.501148    0.538008    11.00000   -1.20000
AFIX   0
C3    2    0.325018    0.415604    0.684804    11.00000    0.02069    0.01183 =
         0.01480   -0.00035    0.00534    0.00134
AFIX  43
H3    3    0.293548    0.569227    0.689992    11.00000   -1.20000
AFIX   0
C4    2    0.317135    0.229939    0.768103    11.00000    0.01809    0.01411 =
         0.01564    0.00065    0.00661    0.00190
AFIX  43
H4    3    0.281388    0.260838    0.830586    11.00000   -1.20000
AFIX   0
C5    2    0.360335   -0.000783    0.762442    11.00000    0.01712    0.01324 =
         0.01573    0.00109    0.00472    0.00073
AFIX  43
H5    3    0.356899   -0.123255    0.822465    11.00000   -1.20000
AFIX   0
C6    2    0.408319   -0.046276    0.666985    11.00000    0.01566    0.01225 =
         0.01530    0.00011    0.00420    0.00015
AFIX  43
H6    3    0.432706   -0.203540    0.656412    11.00000   -1.20000
AFIX   0
N2    1    0.991964    0.110848    0.981780    11.00000    0.01863    0.01385 =
         0.01719    0.00250    0.00756    0.00278
C7    2    0.921721    0.139672    0.834790    11.00000    0.01271    0.01304 =
         0.01437    0.00183    0.00438    0.00103
C8    2    0.904823   -0.050398    0.739834    11.00000    0.02027    0.01200 =
         0.01808    0.00134    0.00779    0.00007
AFIX  43
H8    3    0.929060   -0.207972    0.774275    11.00000   -1.20000
AFIX   0
C9    2    0.852398   -0.004836    0.595496    11.00000    0.01235    0.01367 =
         0.01544   -0.00023    0.00278   -0.00023
AFIX  43
H9    3    0.840504   -0.129622    0.530195    11.00000   -1.20000
AFIX   0
C10   2    0.817946    0.229609    0.549911    11.00000    0.01820    0.01429 =
         0.01710    0.00072    0.00661    0.00018
AFIX  43
H10   3    0.782848    0.263394    0.452044    11.00000   -1.20000
AFIX   0
C11   2    0.833444    0.415972    0.643603    11.00000    0.01677    0.01243 =
         0.01469    0.00087    0.00396    0.00114
AFIX  43
H11   3    0.808796    0.573114    0.608563    11.00000   -1.20000
AFIX   0
C12   2    0.884887    0.373596    0.788499    11.00000    0.01852    0.01298 =
         0.01664    0.00148    0.00641    0.00198
AFIX  43
H12   3    0.894445    0.498601    0.852925    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0173_bn1 in P2(1)/c
REM wR2 = 0.2140, GooF = S = 1.092, Restrained GooF = 1.077 for all data
REM R1 = 0.0693 for 2268 Fo > 4sig(Fo) and 0.0767 for all 2737 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.1660      0.0000

REM Highest difference peak  0.542,  deepest hole -0.371,  1-sigma level  0.104
Q1    1   0.8610 -0.0088  0.6554  11.00000  0.05    0.54
Q2    1   0.3525  0.0010  0.6998  11.00000  0.05    0.48
Q3    1   0.8808  0.2493  0.7899  11.00000  0.05    0.48
Q4    1   0.3135  0.4327  0.6172  11.00000  0.05    0.45
Q5    1   0.8650  0.3829  0.7277  11.00000  0.05    0.42
Q6    1   0.4678  0.1226  0.5531  11.00000  0.05    0.37
Q7    1   0.7892  0.1044  0.5415  11.00000  0.05    0.36
Q8    1   0.8514  0.3559  0.6009  11.00000  0.05    0.35
Q9    1   0.9639  0.1159  0.9033  11.00000  0.05    0.34
Q10   1   0.3319 -0.0051  0.5390  11.00000  0.05    0.31
Q11   1   0.4454  0.2559  0.6359  11.00000  0.05    0.31
Q12   1   0.3694  0.3084  0.7356  11.00000  0.05    0.30
Q13   1   0.4017 -0.2641  0.8026  11.00000  0.05    0.29
Q14   1   0.9272 -0.0282  0.9378  11.00000  0.05    0.28
Q15   1   0.3483  0.2212  0.9235  11.00000  0.05    0.28
Q16   1   0.2365  0.1432  0.6471  11.00000  0.05    0.27
Q17   1   0.8210  0.2838  0.6063  11.00000  0.05    0.27
Q18   1   0.7423  0.5418  0.5786  11.00000  0.05    0.27
Q19   1   1.0733  0.2349  1.0486  11.00000  0.05    0.26
Q20   1   0.3354  0.2837  0.5065  11.00000  0.05    0.26
;
_shelx_res_checksum              12694
####################################################################### 
# 
# 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_21p8GPa
_database_code_depnum_ccdc_archive 'CCDC 2336594'
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_21p8GPa         
;
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_PLAT411_AZO_21p8GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.63 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_21p8GPa         
;
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_21p8GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        525 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                   11.719(9)
_cell_length_b                   5.5018(2)
_cell_length_c                   10.440(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.41(7)
_cell_angle_gamma                90
_cell_volume                     602.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       21810000
_cell_measurement_reflns_used    482
_cell_measurement_theta_min      2.4780
_cell_measurement_theta_max      20.4590

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.008
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.50184
_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         21810000
_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      -0.0389574591
_diffrn_orient_matrix_UB_12      0.0059685513
_diffrn_orient_matrix_UB_13      -0.0215273708
_diffrn_orient_matrix_UB_21      0.0029179828
_diffrn_orient_matrix_UB_22      0.0228111282
_diffrn_orient_matrix_UB_23      -0.0357747264
_diffrn_orient_matrix_UB_31      -0.0022438194
_diffrn_orient_matrix_UB_32      -0.0706324654
_diffrn_orient_matrix_UB_33      -0.0133165617
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2695
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0117
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_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         2.251
_diffrn_reflns_theta_max         21.604
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.226
_diffrn_measured_fraction_theta_full 0.351
_diffrn_reflns_Laue_measured_fraction_max 0.226
_diffrn_reflns_Laue_measured_fraction_full 0.351
_diffrn_reflns_point_group_measured_fraction_max 0.226
_diffrn_reflns_point_group_measured_fraction_full 0.351
_reflns_number_total             2695
_reflns_number_gt                2195
_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 11.3%. 
 3 low-resolution reflections, that were affected by beamstop, were removed 
 from refinemet ( [-1 1 -1] [2 -1 0] [3 -1 -1] ). Some other reflections were 
 removed 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)+(0.1752P)²+0.0255P] 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         2695
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0769
_refine_ls_wR_factor_ref         0.2470
_refine_ls_wR_factor_gt          0.2354
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.147
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.118
_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(6) 0.1107(4) 0.5086(4) 0.0151(19) Uani 1 1 d . U . . .
C1 C 0.4211(8) 0.1423(5) 0.5857(5) 0.016(2) Uani 1 1 d . U . . .
C2 C 0.3803(7) 0.3745(5) 0.5927(5) 0.016(2) Uani 1 1 d . U . . .
H2 H 0.389684 0.499818 0.538384 0.019 Uiso 1 1 calc R U . . .
C3 C 0.3248(7) 0.4150(5) 0.6834(5) 0.017(2) Uani 1 1 d . U . . .
H3 H 0.292617 0.567851 0.687422 0.020 Uiso 1 1 calc R U . . .
C4 C 0.3172(7) 0.2301(5) 0.7671(5) 0.016(2) Uani 1 1 d . U . . .
H4 H 0.281451 0.260926 0.829110 0.019 Uiso 1 1 calc R U . . .
C5 C 0.3610(7) -0.0001(5) 0.7621(5) 0.017(2) Uani 1 1 d . U . . .
H5 H 0.358242 -0.121842 0.822429 0.020 Uiso 1 1 calc R U . . .
C6 C 0.4085(7) -0.0457(5) 0.6668(5) 0.017(2) Uani 1 1 d . U . . .
H6 H 0.432419 -0.202687 0.656121 0.021 Uiso 1 1 calc R U . . .
N2 N 0.9916(6) 0.1103(4) 0.9814(4) 0.0169(19) Uani 1 1 d . U . . .
C7 C 0.9215(7) 0.1381(5) 0.8348(5) 0.015(2) Uani 1 1 d . U . . .
C8 C 0.9053(7) -0.0521(5) 0.7404(5) 0.018(2) Uani 1 1 d . U . . .
H8 H 0.929711 -0.209121 0.774653 0.022 Uiso 1 1 calc R U . . .
C9 C 0.8533(7) -0.0061(5) 0.5970(5) 0.016(2) Uani 1 1 d . U . . .
H9 H 0.842525 -0.130390 0.532156 0.020 Uiso 1 1 calc R U . . .
C10 C 0.8174(7) 0.2271(5) 0.5507(5) 0.018(2) Uani 1 1 d . U . . .
H10 H 0.781400 0.259998 0.453200 0.022 Uiso 1 1 calc R U . . .
C11 C 0.8330(8) 0.4134(5) 0.6444(5) 0.017(2) Uani 1 1 d . U . . .
H11 H 0.808194 0.570069 0.609746 0.020 Uiso 1 1 calc R U . . .
C12 C 0.8851(8) 0.3707(5) 0.7889(5) 0.017(2) Uani 1 1 d . U . . .
H12 H 0.895153 0.495405 0.853159 0.020 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) 0.0160(11) 0.012(2) -0.0010(9) 0.001(4) 0.0016(14)
C1 0.019(6) 0.0145(11) 0.013(2) -0.0009(10) 0.005(4) -0.0006(16)
C2 0.015(7) 0.0149(12) 0.013(3) -0.0002(10) 0.002(4) -0.0002(16)
C3 0.018(6) 0.0147(12) 0.012(3) 0.0002(10) 0.002(4) 0.0017(16)
C4 0.014(6) 0.0167(12) 0.015(3) -0.0004(11) 0.005(4) 0.0003(17)
C5 0.016(7) 0.0153(12) 0.015(3) 0.0007(11) 0.003(4) -0.0003(17)
C6 0.018(6) 0.0141(11) 0.015(3) -0.0004(11) 0.004(4) -0.0002(16)
N2 0.017(6) 0.0156(12) 0.014(2) 0.0016(9) 0.004(4) 0.0019(14)
C7 0.013(6) 0.0156(12) 0.012(3) 0.0018(10) 0.002(4) 0.0014(16)
C8 0.020(7) 0.0144(11) 0.017(3) 0.0018(11) 0.006(4) 0.0010(17)
C9 0.013(7) 0.0159(12) 0.016(3) -0.0005(11) 0.002(4) -0.0009(16)
C10 0.018(7) 0.0173(12) 0.016(3) 0.0012(11) 0.005(4) -0.0002(17)
C11 0.017(6) 0.0151(12) 0.015(3) 0.0024(11) 0.003(4) 0.0026(16)
C12 0.017(7) 0.0153(12) 0.015(3) 0.0011(10) 0.003(4) 0.0014(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 1.263(4) 3_656 ?
N1 C1 1.390(5) . ?
C1 C2 1.377(5) . ?
C1 C6 1.386(4) . ?
C2 C3 1.384(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.362(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.262(5) 3_757 ?
N2 C7 1.387(7) . ?
C7 C12 1.367(5) . ?
C7 C8 1.391(4) . ?
C8 C9 1.366(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 1.372(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 112.5(4) 3_656 . ?
C2 C1 C6 121.7(3) . . ?
C2 C1 N1 117.1(3) . . ?
C6 C1 N1 120.7(4) . . ?
C1 C2 C3 117.8(3) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 121.9(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 118.5(2) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 119.9(3) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N2 N2 C7 112.4(4) 3_757 . ?
C12 C7 N2 115.4(3) . . ?
C12 C7 C8 122.2(4) . . ?
N2 C7 C8 121.7(4) . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 118.5(3) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C9 C10 C11 121.7(4) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C10 C11 C12 120.6(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C7 C12 C11 117.6(3) . . ?
C7 C12 H12 121.2 . . ?
C11 C12 H12 121.2 . . ?

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 -170.9(8) 3_656 . . . ?
N1 N1 C1 C6 17.5(11) 3_656 . . . ?
C6 C1 C2 C3 -0.5(12) . . . . ?
N1 C1 C2 C3 -172.1(6) . . . . ?
C1 C2 C3 C4 3.0(11) . . . . ?
C2 C3 C4 C5 -1.5(11) . . . . ?
C3 C4 C5 C6 -2.6(11) . . . . ?
C4 C5 C6 C1 5.1(11) . . . . ?
C2 C1 C6 C5 -3.6(12) . . . . ?
N1 C1 C6 C5 167.7(7) . . . . ?
N2 N2 C7 C12 171.6(7) 3_757 . . . ?
N2 N2 C7 C8 -17.1(10) 3_757 . . . ?
C12 C7 C8 C9 1.1(11) . . . . ?
N2 C7 C8 C9 -169.6(6) . . . . ?
C7 C8 C9 C10 -0.7(10) . . . . ?
C8 C9 C10 C11 0.4(10) . . . . ?
C9 C10 C11 C12 -0.4(10) . . . . ?
N2 C7 C12 C11 170.1(6) . . . . ?
C8 C7 C12 C11 -1.1(11) . . . . ?
C10 C11 C12 C7 0.8(11) . . . . ?


_shelx_res_file                  
;
TITL sample_0165_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 11:04:16 on 27-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  11.719222   5.501849  10.439634  90.0000 116.4083  90.0000
ZERR    4.00   0.009307   0.000245   0.003621   0.0000   0.0717   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 10 -4 -10
OMIT 4 -2 -1
OMIT -1 1 -1
OMIT -4 1 7
OMIT 2 -1 0
OMIT 3 -1 -1
OMIT -3 -1 5
OMIT -3 1 5
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.175200    0.025500
BASF   0.11289
FVAR      25.70171
N1    1    0.490940    0.110669    0.508602    11.00000    0.01179    0.01604 =
         0.01239   -0.00102    0.00081    0.00164
C1    2    0.421117    0.142350    0.585674    11.00000    0.01907    0.01449 =
         0.01311   -0.00092    0.00493   -0.00065
C2    2    0.380279    0.374497    0.592717    11.00000    0.01460    0.01486 =
         0.01307   -0.00022    0.00248   -0.00022
AFIX  43
H2    3    0.389684    0.499818    0.538384    11.00000   -1.20000
AFIX   0
C3    2    0.324774    0.415037    0.683364    11.00000    0.01845    0.01471 =
         0.01236    0.00015    0.00234    0.00167
AFIX  43
H3    3    0.292617    0.567851    0.687422    11.00000   -1.20000
AFIX   0
C4    2    0.317210    0.230070    0.767096    11.00000    0.01439    0.01669 =
         0.01498   -0.00041    0.00464    0.00027
AFIX  43
H4    3    0.281451    0.260926    0.829110    11.00000   -1.20000
AFIX   0
C5    2    0.361008   -0.000091    0.762076    11.00000    0.01631    0.01533 =
         0.01455    0.00070    0.00274   -0.00029
AFIX  43
H5    3    0.358242   -0.121842    0.822429    11.00000   -1.20000
AFIX   0
C6    2    0.408504   -0.045664    0.666754    11.00000    0.01802    0.01413 =
         0.01534   -0.00037    0.00393   -0.00022
AFIX  43
H6    3    0.432419   -0.202687    0.656121    11.00000   -1.20000
AFIX   0
N2    1    0.991567    0.110257    0.981406    11.00000    0.01727    0.01564 =
         0.01407    0.00164    0.00352    0.00189
C7    2    0.921479    0.138062    0.834766    11.00000    0.01308    0.01560 =
         0.01231    0.00176    0.00237    0.00139
C8    2    0.905320   -0.052111    0.740396    11.00000    0.01972    0.01441 =
         0.01748    0.00184    0.00611    0.00097
AFIX  43
H8    3    0.929711   -0.209121    0.774653    11.00000   -1.20000
AFIX   0
C9    2    0.853301   -0.006134    0.596952    11.00000    0.01297    0.01585 =
         0.01555   -0.00045    0.00207   -0.00091
AFIX  43
H9    3    0.842525   -0.130390    0.532156    11.00000   -1.20000
AFIX   0
C10   2    0.817369    0.227091    0.550703    11.00000    0.01807    0.01728 =
         0.01638    0.00115    0.00528   -0.00024
AFIX  43
H10   3    0.781400    0.259998    0.453200    11.00000   -1.20000
AFIX   0
C11   2    0.833039    0.413411    0.644411    11.00000    0.01696    0.01511 =
         0.01470    0.00240    0.00315    0.00257
AFIX  43
H11   3    0.808194    0.570069    0.609746    11.00000   -1.20000
AFIX   0
C12   2    0.885058    0.370663    0.788865    11.00000    0.01686    0.01528 =
         0.01475    0.00106    0.00328    0.00142
AFIX  43
H12   3    0.895153    0.495405    0.853159    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0165_bn1 in P2(1)/c
REM wR2 = 0.2470, GooF = S = 1.162, Restrained GooF = 1.147 for all data
REM R1 = 0.0769 for 2195 Fo > 4sig(Fo) and 0.0852 for all 2695 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.1752      0.0255

REM Highest difference peak  0.566,  deepest hole -0.432,  1-sigma level  0.118
Q1    1   0.3615  0.0021  0.7090  11.00000  0.05    0.57
Q2    1   0.8603 -0.0053  0.6544  11.00000  0.05    0.52
Q3    1   0.9474  0.1329  0.8973  11.00000  0.05    0.45
Q4    1   1.0536  0.0239  1.0377  11.00000  0.05    0.39
Q5    1   0.8608  0.3903  0.7220  11.00000  0.05    0.38
Q6    1   0.8427  0.0083  0.7219  11.00000  0.05    0.37
Q7    1   0.8821  0.3258  0.6407  11.00000  0.05    0.36
Q8    1   0.5097  0.0226  0.5939  11.00000  0.05    0.35
Q9    1   0.8647  0.7228  0.9061  11.00000  0.05    0.34
Q10   1   0.1963  0.3979  0.6884  11.00000  0.05    0.34
Q11   1   0.4287  0.1040  0.8193  11.00000  0.05    0.34
Q12   1   0.2336  0.3156  0.6678  11.00000  0.05    0.34
Q13   1   0.3303  0.2605  0.4889  11.00000  0.05    0.33
Q14   1   0.7185  0.1388  0.4600  11.00000  0.05    0.33
Q15   1   0.4131 -0.2806  0.8779  11.00000  0.05    0.33
Q16   1   0.5027  0.4732  0.5511  11.00000  0.05    0.32
Q17   1   0.8771  0.2481  0.7911  11.00000  0.05    0.32
Q18   1   0.7934  0.3081  0.6952  11.00000  0.05    0.32
Q19   1   0.9194  0.2916  0.7386  11.00000  0.05    0.32
Q20   1   0.4531  0.2683  0.6947  11.00000  0.05    0.31
;
_shelx_res_checksum              84325
####################################################################### 
# 
# 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_26p2GPa
_database_code_depnum_ccdc_archive 'CCDC 2336603'
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_26p2GPa         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.338 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_26p2GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.61 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_PLAT097_AZO_26p2GPa         
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.81 eA-3  
RESPONSE: The residual density is in the center of a C-C bond of a phenyl 
ring.
;
_vrf_PLAT149_AZO_26p2GPa         
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.20 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_26p2GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        516 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             2023-03-17
_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                   11.44(3)
_cell_length_b                   5.4806(6)
_cell_length_c                   10.344(11)
_cell_angle_alpha                90
_cell_angle_beta                 116.8(2)
_cell_angle_gamma                90
_cell_volume                     579.3(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       26190000
_cell_measurement_reflns_used    372
_cell_measurement_theta_min      2.4910
_cell_measurement_theta_max      20.0790

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.089
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.39410
_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         26190000
_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      -0.0400728483
_diffrn_orient_matrix_UB_12      0.0053320177
_diffrn_orient_matrix_UB_13      -0.0219314012
_diffrn_orient_matrix_UB_21      0.0027235804
_diffrn_orient_matrix_UB_22      0.0235621540
_diffrn_orient_matrix_UB_23      -0.0361397381
_diffrn_orient_matrix_UB_31      -0.0018887615
_diffrn_orient_matrix_UB_32      -0.0707108828
_diffrn_orient_matrix_UB_33      -0.0135202720
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2459
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0122
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_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         2.272
_diffrn_reflns_theta_max         21.758
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.221
_diffrn_measured_fraction_theta_full 0.338
_diffrn_reflns_Laue_measured_fraction_max 0.221
_diffrn_reflns_Laue_measured_fraction_full 0.338
_diffrn_reflns_point_group_measured_fraction_max 0.221
_diffrn_reflns_point_group_measured_fraction_full 0.338
_reflns_number_total             2459
_reflns_number_gt                1822
_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 14.5%. 
 6 low-resolution reflections, that were affected by beamstop, were removed 
 from refinemet. Some other reflections were removed 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)+(0.1771P)²+0.0831P] 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         2459
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0871
_refine_ls_wR_factor_ref         0.2850
_refine_ls_wR_factor_gt          0.2703
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.809
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.105
_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(9) 0.1114(5) 0.5085(6) 0.025(2) Uani 1 1 d . U . . .
C1 C 0.4208(11) 0.1433(6) 0.5864(7) 0.025(3) Uani 1 1 d . U . . .
C2 C 0.3791(11) 0.3751(6) 0.5939(7) 0.024(3) Uani 1 1 d . U . . .
H2 H 0.386921 0.500863 0.537941 0.029 Uiso 1 1 calc R U . . .
C3 C 0.3254(11) 0.4151(6) 0.6872(7) 0.026(3) Uani 1 1 d . U . . .
H3 H 0.295536 0.569942 0.694149 0.031 Uiso 1 1 calc R U . . .
C4 C 0.3156(11) 0.2291(7) 0.7696(7) 0.026(3) Uani 1 1 d . U . . .
H4 H 0.279233 0.260315 0.832174 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3578(10) -0.0019(6) 0.7626(7) 0.026(3) Uani 1 1 d . U . . .
H5 H 0.353016 -0.125248 0.821789 0.031 Uiso 1 1 calc R U . . .
C6 C 0.4070(10) -0.0473(7) 0.6672(7) 0.025(3) Uani 1 1 d . U . . .
H6 H 0.431193 -0.204962 0.656034 0.030 Uiso 1 1 calc R U . . .
N2 N 0.9908(9) 0.1115(5) 0.9822(6) 0.026(2) Uani 1 1 d . U . . .
C7 C 0.9211(11) 0.1434(7) 0.8348(7) 0.026(3) Uani 1 1 d . U . . .
C8 C 0.9048(11) -0.0453(7) 0.7397(7) 0.028(3) Uani 1 1 d . U . . .
H8 H 0.929256 -0.203052 0.774475 0.034 Uiso 1 1 calc R U . . .
C9 C 0.8528(11) -0.0001(7) 0.5941(7) 0.027(3) Uani 1 1 d . U . . .
H9 H 0.841459 -0.124868 0.528541 0.032 Uiso 1 1 calc R U . . .
C10 C 0.8182(11) 0.2341(6) 0.5486(7) 0.029(3) Uani 1 1 d . U . . .
H10 H 0.780497 0.267864 0.449992 0.035 Uiso 1 1 calc R U . . .
C11 C 0.8373(11) 0.4211(7) 0.6439(7) 0.030(3) Uani 1 1 d . U . . .
H11 H 0.816700 0.579810 0.609171 0.036 Uiso 1 1 calc R U . . .
C12 C 0.8859(11) 0.3788(7) 0.7890(7) 0.026(3) Uani 1 1 d . U . . .
H12 H 0.894654 0.503677 0.853663 0.032 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(8) 0.0207(15) 0.022(3) -0.0004(12) 0.004(4) 0.0026(19)
C1 0.030(8) 0.0198(14) 0.019(3) 0.0008(15) 0.004(5) 0.002(2)
C2 0.023(8) 0.0214(15) 0.020(3) 0.0018(14) 0.002(5) 0.002(2)
C3 0.030(8) 0.0184(15) 0.022(3) 0.0004(14) 0.005(5) 0.001(2)
C4 0.029(8) 0.0223(16) 0.020(3) 0.0006(15) 0.004(5) 0.000(2)
C5 0.027(8) 0.0207(16) 0.021(3) 0.0014(14) 0.003(5) 0.001(2)
C6 0.027(8) 0.0188(14) 0.022(3) -0.0001(15) 0.004(5) 0.001(2)
N2 0.026(8) 0.0214(16) 0.022(3) 0.0035(13) 0.005(5) 0.0023(19)
C7 0.028(8) 0.0241(16) 0.023(3) 0.0049(15) 0.008(5) 0.003(2)
C8 0.033(8) 0.0221(15) 0.025(3) 0.0042(16) 0.009(5) 0.003(2)
C9 0.026(9) 0.0238(17) 0.020(3) 0.0014(15) 0.002(5) 0.002(2)
C10 0.032(9) 0.0256(17) 0.024(3) 0.0007(16) 0.008(5) 0.003(2)
C11 0.038(8) 0.0237(16) 0.022(3) 0.0036(16) 0.009(5) 0.006(2)
C12 0.028(9) 0.0234(16) 0.023(3) 0.0037(15) 0.006(5) 0.004(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 1.264(6) 3_656 ?
N1 C1 1.379(8) . ?
C1 C2 1.372(7) . ?
C1 C6 1.390(5) . ?
C2 C3 1.374(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.362(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.267(6) 3_757 ?
N2 C7 1.377(10) . ?
C7 C12 1.371(6) . ?
C7 C8 1.381(6) . ?
C8 C9 1.370(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.363(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.365(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 112.4(5) 3_656 . ?
C2 C1 N1 117.3(4) . . ?
C2 C1 C6 121.7(5) . . ?
N1 C1 C6 120.6(5) . . ?
C1 C2 C3 117.7(4) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 120.5(4) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 121.8(5) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 118.6(4) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 119.6(4) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2 N2 C7 112.5(6) 3_757 . ?
C12 C7 N2 115.8(5) . . ?
C12 C7 C8 122.3(6) . . ?
N2 C7 C8 121.2(5) . . ?
C9 C8 C7 120.0(5) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 117.7(4) . . ?
C10 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
C9 C10 C11 121.9(6) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C12 C11 C10 121.2(4) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C7 116.8(4) . . ?
C11 C12 H12 121.6 . . ?
C7 C12 H12 121.6 . . ?

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 -171.0(11) 3_656 . . . ?
N1 N1 C1 C6 16.2(15) 3_656 . . . ?
N1 C1 C2 C3 -171.2(9) . . . . ?
C6 C1 C2 C3 1.5(17) . . . . ?
C1 C2 C3 C4 0.5(16) . . . . ?
C2 C3 C4 C5 -0.2(16) . . . . ?
C3 C4 C5 C6 -2.1(16) . . . . ?
C4 C5 C6 C1 4.0(15) . . . . ?
C2 C1 C6 C5 -3.8(16) . . . . ?
N1 C1 C6 C5 168.6(9) . . . . ?
N2 N2 C7 C12 173.6(9) 3_757 . . . ?
N2 N2 C7 C8 -15.3(14) 3_757 . . . ?
C12 C7 C8 C9 0.5(16) . . . . ?
N2 C7 C8 C9 -170.0(9) . . . . ?
C7 C8 C9 C10 -0.2(15) . . . . ?
C8 C9 C10 C11 1.7(15) . . . . ?
C9 C10 C11 C12 -3.4(17) . . . . ?
C10 C11 C12 C7 3.5(16) . . . . ?
N2 C7 C12 C11 168.9(9) . . . . ?
C8 C7 C12 C11 -2.1(15) . . . . ?


_shelx_res_file                  
;
TITL sample_0188_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 17:43:32 on 28-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  11.444719   5.480575  10.343767  90.0000 116.7682  90.0000
ZERR    4.00   0.027275   0.000604   0.010821   0.0000   0.2171   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 3 -1
OMIT -1 3 1
OMIT 0 2 -2
OMIT 0 -2 2
OMIT -2 -5 -2
OMIT -1 1 -1
OMIT 0 2 0
OMIT 0 -2 0
OMIT 2 -1 0
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.177100    0.083100
BASF   0.14470
FVAR      26.69559
N1    1    0.490783    0.111353    0.508496    11.00000    0.02452    0.02068 =
         0.02185   -0.00040    0.00374    0.00265
C1    2    0.420839    0.143271    0.586447    11.00000    0.02963    0.01980 =
         0.01895    0.00077    0.00419    0.00177
C2    2    0.379130    0.375137    0.593949    11.00000    0.02268    0.02140 =
         0.01970    0.00184    0.00188    0.00206
AFIX  43
H2    3    0.386921    0.500863    0.537941    11.00000   -1.20000
AFIX   0
C3    2    0.325422    0.415074    0.687159    11.00000    0.03031    0.01840 =
         0.02177    0.00037    0.00531    0.00110
AFIX  43
H3    3    0.295536    0.569942    0.694149    11.00000   -1.20000
AFIX   0
C4    2    0.315613    0.229119    0.769563    11.00000    0.02873    0.02226 =
         0.01971    0.00056    0.00401    0.00040
AFIX  43
H4    3    0.279233    0.260315    0.832174    11.00000   -1.20000
AFIX   0
C5    2    0.357822   -0.001932    0.762604    11.00000    0.02677    0.02068 =
         0.02135    0.00138    0.00293    0.00143
AFIX  43
H5    3    0.353016   -0.125248    0.821789    11.00000   -1.20000
AFIX   0
C6    2    0.407000   -0.047338    0.667163    11.00000    0.02686    0.01884 =
         0.02185   -0.00007    0.00361    0.00136
AFIX  43
H6    3    0.431193   -0.204962    0.656034    11.00000   -1.20000
AFIX   0
N2    1    0.990833    0.111518    0.982205    11.00000    0.02627    0.02140 =
         0.02235    0.00346    0.00481    0.00225
C7    2    0.921111    0.143447    0.834822    11.00000    0.02787    0.02405 =
         0.02345    0.00495    0.00800    0.00303
C8    2    0.904848   -0.045263    0.739668    11.00000    0.03338    0.02210 =
         0.02484    0.00416    0.00941    0.00348
AFIX  43
H8    3    0.929256   -0.203052    0.774475    11.00000   -1.20000
AFIX   0
C9    2    0.852791   -0.000096    0.594086    11.00000    0.02630    0.02378 =
         0.02039    0.00140    0.00195    0.00208
AFIX  43
H9    3    0.841459   -0.124868    0.528541    11.00000   -1.20000
AFIX   0
C10   2    0.818177    0.234055    0.548626    11.00000    0.03194    0.02562 =
         0.02358    0.00070    0.00764    0.00346
AFIX  43
H10   3    0.780497    0.267864    0.449992    11.00000   -1.20000
AFIX   0
C11   2    0.837251    0.421120    0.643946    11.00000    0.03845    0.02373 =
         0.02225    0.00356    0.00879    0.00607
AFIX  43
H11   3    0.816700    0.579810    0.609171    11.00000   -1.20000
AFIX   0
C12   2    0.885865    0.378830    0.789013    11.00000    0.02769    0.02340 =
         0.02263    0.00373    0.00634    0.00422
AFIX  43
H12   3    0.894654    0.503677    0.853663    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0188_bn1 in P2(1)/c
REM wR2 = 0.2850, GooF = S = 1.165, Restrained GooF = 1.161 for all data
REM R1 = 0.0871 for 1822 Fo > 4sig(Fo) and 0.1014 for all 2459 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.1771      0.0831

REM Highest difference peak  0.809,  deepest hole -0.391,  1-sigma level  0.105
Q1    1   0.3452  0.3847  0.6338  11.00000  0.05    0.81
Q2    1   0.3712 -0.0395  0.7103  11.00000  0.05    0.72
Q3    1   0.4613  0.1219  0.5491  11.00000  0.05    0.64
Q4    1   0.8648  0.4084  0.7212  11.00000  0.05    0.46
Q5    1   0.9769  0.1147  0.9226  11.00000  0.05    0.36
Q6    1   0.9098 -0.0048  0.8147  11.00000  0.05    0.36
Q7    1   0.9437  0.4716  0.8413  11.00000  0.05    0.35
Q8    1   0.3626  0.3935  0.5114  11.00000  0.05    0.32
Q9    1   0.9190  0.4874  0.6597  11.00000  0.05    0.31
Q10   1   0.3718  0.3101  0.7361  11.00000  0.05    0.30
Q11   1   0.8877  0.3005  0.5540  11.00000  0.05    0.29
Q12   1   0.3084  0.2547  0.7136  11.00000  0.05    0.28
Q13   1   0.8313  0.2676  0.4872  11.00000  0.05    0.27
Q14   1   0.8373  0.3822  0.5812  11.00000  0.05    0.27
Q15   1   0.2949  0.3910  0.7331  11.00000  0.05    0.27
Q16   1   0.8221  0.2786  0.6027  11.00000  0.05    0.26
Q17   1   0.8418 -0.0789  0.4618  11.00000  0.05    0.26
Q18   1   0.6941  0.1597  0.4685  11.00000  0.05    0.24
Q19   1   0.4200  0.2159  0.4353  11.00000  0.05    0.23
Q20   1   0.4974  0.0394  0.6981  11.00000  0.05    0.23
;
_shelx_res_checksum              52625
####################################################################### 
# 
# 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_23GPa
_database_code_depnum_ccdc_archive 'CCDC 2336597'
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_23GPa           
;
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_23GPa           
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.63 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_23GPa           
;
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_23GPa           
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        507 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             2023-03-17
_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                   11.660(10)
_cell_length_b                   5.4890(2)
_cell_length_c                   10.407(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.47(8)
_cell_angle_gamma                90
_cell_volume                     596.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       23070000
_cell_measurement_reflns_used    502
_cell_measurement_theta_min      2.2550
_cell_measurement_theta_max      20.7130

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.030
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.40106
_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         23070000
_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      -0.0392357053
_diffrn_orient_matrix_UB_12      0.0056955069
_diffrn_orient_matrix_UB_13      -0.0216016358
_diffrn_orient_matrix_UB_21      0.0028171063
_diffrn_orient_matrix_UB_22      0.0230038479
_diffrn_orient_matrix_UB_23      -0.0359101226
_diffrn_orient_matrix_UB_31      -0.0021380340
_diffrn_orient_matrix_UB_32      -0.0707260959
_diffrn_orient_matrix_UB_33      -0.0133558876
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2805
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0127
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_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         2.258
_diffrn_reflns_theta_max         21.668
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.227
_diffrn_measured_fraction_theta_full 0.350
_diffrn_reflns_Laue_measured_fraction_max 0.227
_diffrn_reflns_Laue_measured_fraction_full 0.350
_diffrn_reflns_point_group_measured_fraction_max 0.227
_diffrn_reflns_point_group_measured_fraction_full 0.350
_reflns_number_total             2805
_reflns_number_gt                2309
_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 12.9%. 
 2 low-resolution reflections, that were affected by beamstop, were removed 
 from refinemet ( [-1 1 -1] [2 -1 0] ). Some other reflections were removed 
 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)+(0.1575P)²+0.0159P] 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         2805
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.2143
_refine_ls_wR_factor_gt          0.2058
_refine_ls_goodness_of_fit_ref   1.117
_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         0.519
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.096
_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 0.4911(5) 0.1111(3) 0.5089(4) 0.0136(17) Uani 1 1 d . U . . .
C1 C 0.4207(7) 0.1426(4) 0.5856(5) 0.0145(18) Uani 1 1 d . U . . .
C2 C 0.3801(6) 0.3752(4) 0.5931(4) 0.0139(19) Uani 1 1 d . U . . .
H2 H 0.389381 0.500858 0.538479 0.017 Uiso 1 1 calc R U . . .
C3 C 0.3251(7) 0.4156(4) 0.6844(4) 0.0160(18) Uani 1 1 d . U . . .
H3 H 0.293537 0.569167 0.689295 0.019 Uiso 1 1 calc R U . . .
C4 C 0.3170(6) 0.2300(4) 0.7677(4) 0.0153(18) Uani 1 1 d . U . . .
H4 H 0.280818 0.260681 0.829664 0.018 Uiso 1 1 calc R U . . .
C5 C 0.3607(6) -0.0004(4) 0.7624(4) 0.0155(19) Uani 1 1 d . U . . .
H5 H 0.357888 -0.122505 0.822855 0.019 Uiso 1 1 calc R U . . .
C6 C 0.4082(6) -0.0462(4) 0.6669(4) 0.0153(18) Uani 1 1 d . U . . .
H6 H 0.432240 -0.203534 0.656163 0.018 Uiso 1 1 calc R U . . .
N2 N 0.9913(6) 0.1106(3) 0.9813(4) 0.0158(17) Uani 1 1 d . U . . .
C7 C 0.9216(6) 0.1393(4) 0.8348(4) 0.0137(18) Uani 1 1 d . U . . .
C8 C 0.9049(6) -0.0511(4) 0.7399(4) 0.0173(19) Uani 1 1 d . U . . .
H8 H 0.929177 -0.208572 0.774345 0.021 Uiso 1 1 calc R U . . .
C9 C 0.8527(6) -0.0055(4) 0.5959(4) 0.0156(19) Uani 1 1 d . U . . .
H9 H 0.841203 -0.130146 0.530788 0.019 Uiso 1 1 calc R U . . .
C10 C 0.8177(6) 0.2288(4) 0.5502(4) 0.0167(18) Uani 1 1 d . U . . .
H10 H 0.782293 0.262268 0.452392 0.020 Uiso 1 1 calc R U . . .
C11 C 0.8332(7) 0.4151(4) 0.6438(5) 0.0159(18) Uani 1 1 d . U . . .
H11 H 0.808509 0.572208 0.608880 0.019 Uiso 1 1 calc R U . . .
C12 C 0.8847(7) 0.3727(4) 0.7884(4) 0.0156(19) Uani 1 1 d . U . . .
H12 H 0.894212 0.497690 0.852729 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 0.009(5) 0.0148(10) 0.012(2) -0.0005(8) 0.000(3) 0.0021(12)
C1 0.015(6) 0.0133(9) 0.013(2) -0.0005(9) 0.004(3) 0.0001(14)
C2 0.011(6) 0.0142(10) 0.012(2) 0.0001(9) 0.001(4) 0.0002(14)
C3 0.017(6) 0.0131(10) 0.014(2) -0.0001(9) 0.004(4) 0.0013(14)
C4 0.014(6) 0.0153(10) 0.015(2) 0.0003(9) 0.005(4) 0.0016(14)
C5 0.014(6) 0.0141(11) 0.015(2) 0.0008(10) 0.003(4) 0.0005(15)
C6 0.014(6) 0.0131(10) 0.015(2) 0.0000(10) 0.004(3) 0.0004(15)
N2 0.015(5) 0.0149(11) 0.015(2) 0.0021(8) 0.005(3) 0.0023(12)
C7 0.011(6) 0.0145(10) 0.012(2) 0.0015(9) 0.002(4) 0.0008(14)
C8 0.020(6) 0.0129(10) 0.018(2) 0.0012(10) 0.007(4) 0.0001(15)
C9 0.013(6) 0.0147(11) 0.016(2) -0.0002(10) 0.003(4) 0.0000(15)
C10 0.016(6) 0.0155(11) 0.017(2) 0.0005(10) 0.005(4) -0.0007(15)
C11 0.016(6) 0.0135(10) 0.014(2) 0.0014(10) 0.003(4) 0.0015(14)
C12 0.015(6) 0.0136(11) 0.015(2) 0.0007(9) 0.004(4) 0.0006(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(5) . ?
C1 C2 1.376(4) . ?
C1 C6 1.386(3) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.359(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.264(4) 3_757 ?
N2 C7 1.381(6) . ?
C7 C12 1.369(4) . ?
C7 C8 1.390(4) . ?
C8 C9 1.366(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.369(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.368(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 112.4(3) 3_656 . ?
C2 C1 C6 121.8(3) . . ?
C2 C1 N1 117.0(2) . . ?
C6 C1 N1 120.5(3) . . ?
C1 C2 C3 117.7(2) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 121.9(3) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 118.6(2) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N2 N2 C7 112.6(4) 3_757 . ?
C12 C7 N2 115.7(3) . . ?
C12 C7 C8 122.1(4) . . ?
N2 C7 C8 121.7(3) . . ?
C9 C8 C7 119.6(3) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 118.2(3) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
C11 C10 C9 122.0(4) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C10 C11 C12 120.6(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 117.5(3) . . ?
C11 C12 H12 121.3 . . ?
C7 C12 H12 121.3 . . ?

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 -170.8(7) 3_656 . . . ?
N1 N1 C1 C6 18.0(9) 3_656 . . . ?
C6 C1 C2 C3 -0.4(10) . . . . ?
N1 C1 C2 C3 -171.5(5) . . . . ?
C1 C2 C3 C4 2.5(10) . . . . ?
C2 C3 C4 C5 -0.9(10) . . . . ?
C3 C4 C5 C6 -2.9(9) . . . . ?
C4 C5 C6 C1 4.9(9) . . . . ?
C2 C1 C6 C5 -3.4(10) . . . . ?
N1 C1 C6 C5 167.4(6) . . . . ?
N2 N2 C7 C12 171.7(6) 3_757 . . . ?
N2 N2 C7 C8 -16.4(9) 3_757 . . . ?
C12 C7 C8 C9 1.4(9) . . . . ?
N2 C7 C8 C9 -169.9(5) . . . . ?
C7 C8 C9 C10 -0.4(9) . . . . ?
C8 C9 C10 C11 -0.2(9) . . . . ?
C9 C10 C11 C12 -0.2(9) . . . . ?
C10 C11 C12 C7 1.1(9) . . . . ?
N2 C7 C12 C11 170.0(5) . . . . ?
C8 C7 C12 C11 -1.8(9) . . . . ?


_shelx_res_file                  
;
TITL sample_0171_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 16:23:59 on 28-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  11.660106   5.488961  10.406801  90.0000 116.4734  90.0000
ZERR    4.00   0.009701   0.000233   0.003965   0.0000   0.0768   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 -3 -1
OMIT 4 -2 -1
OMIT -4 2 1
OMIT -1 1 -1
OMIT 13 0 -12
OMIT 2 -1 0
OMIT -3 1 5
OMIT -3 -1 5
OMIT -2  2  5
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.157500    0.015900
BASF   0.12903
FVAR      25.29555
N1    1    0.491141    0.111085    0.508873    11.00000    0.00889    0.01478 =
         0.01184   -0.00049   -0.00016    0.00210
C1    2    0.420668    0.142594    0.585613    11.00000    0.01453    0.01328 =
         0.01314   -0.00046    0.00387    0.00007
C2    2    0.380095    0.375196    0.593056    11.00000    0.01082    0.01417 =
         0.01236    0.00008    0.00126    0.00020
AFIX  43
H2    3    0.389381    0.500858    0.538479    11.00000   -1.20000
AFIX   0
C3    2    0.325086    0.415625    0.684405    11.00000    0.01716    0.01312 =
         0.01387   -0.00011    0.00352    0.00129
AFIX  43
H3    3    0.293537    0.569167    0.689295    11.00000   -1.20000
AFIX   0
C4    2    0.316981    0.230027    0.767668    11.00000    0.01412    0.01526 =
         0.01514    0.00028    0.00520    0.00157
AFIX  43
H4    3    0.280818    0.260681    0.829664    11.00000   -1.20000
AFIX   0
C5    2    0.360718   -0.000406    0.762376    11.00000    0.01375    0.01406 =
         0.01478    0.00075    0.00292    0.00050
AFIX  43
H5    3    0.357888   -0.122505    0.822855    11.00000   -1.20000
AFIX   0
C6    2    0.408211   -0.046175    0.666889    11.00000    0.01425    0.01307 =
         0.01527   -0.00001    0.00352    0.00036
AFIX  43
H6    3    0.432240   -0.203534    0.656163    11.00000   -1.20000
AFIX   0
N2    1    0.991311    0.110611    0.981286    11.00000    0.01514    0.01491 =
         0.01534    0.00207    0.00491    0.00230
C7    2    0.921593    0.139257    0.834751    11.00000    0.01103    0.01449 =
         0.01247    0.00150    0.00235    0.00077
C8    2    0.904918   -0.051111    0.739945    11.00000    0.01999    0.01289 =
         0.01761    0.00119    0.00721    0.00008
AFIX  43
H8    3    0.929177   -0.208572    0.774345    11.00000   -1.20000
AFIX   0
C9    2    0.852678   -0.005480    0.595933    11.00000    0.01315    0.01467 =
         0.01574   -0.00020    0.00344   -0.00003
AFIX  43
H9    3    0.841203   -0.130146    0.530788    11.00000   -1.20000
AFIX   0
C10   2    0.817690    0.228759    0.550155    11.00000    0.01598    0.01551 =
         0.01667    0.00051    0.00550   -0.00067
AFIX  43
H10   3    0.782293    0.262268    0.452392    11.00000   -1.20000
AFIX   0
C11   2    0.833191    0.415147    0.643807    11.00000    0.01595    0.01353 =
         0.01411    0.00139    0.00311    0.00146
AFIX  43
H11   3    0.808509    0.572208    0.608880    11.00000   -1.20000
AFIX   0
C12   2    0.884672    0.372693    0.788399    11.00000    0.01468    0.01360 =
         0.01542    0.00065    0.00398    0.00060
AFIX  43
H12   3    0.894212    0.497690    0.852729    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0171_bn1 in P2(1)/c
REM wR2 = 0.2143, GooF = S = 1.117, Restrained GooF = 1.102 for all data
REM R1 = 0.0687 for 2309 Fo > 4sig(Fo) and 0.0764 for all 2805 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.1577      0.0151

REM Highest difference peak  0.519,  deepest hole -0.319,  1-sigma level  0.096
Q1    1   0.8498 -0.0059  0.6471  11.00000  0.05    0.52
Q2    1   0.3277  0.4239  0.6308  11.00000  0.05    0.47
Q3    1   0.3470  0.0031  0.7021  11.00000  0.05    0.45
Q4    1   0.8810  0.2440  0.7904  11.00000  0.05    0.44
Q5    1   0.9505  0.1225  0.8953  11.00000  0.05    0.40
Q6    1   0.8070  0.0993  0.5545  11.00000  0.05    0.39
Q7    1   0.4058 -0.0661  0.7244  11.00000  0.05    0.37
Q8    1   0.4661  0.1062  0.5544  11.00000  0.05    0.32
Q9    1   0.4545  0.2605  0.6399  11.00000  0.05    0.32
Q10   1   0.8364  0.4183  0.6879  11.00000  0.05    0.31
Q11   1   0.9437 -0.0116  0.9449  11.00000  0.05    0.29
Q12   1   0.9095 -0.2581  0.8292  11.00000  0.05    0.29
Q13   1   0.2622  0.3040  0.6816  11.00000  0.05    0.29
Q14   1   0.4195  0.1178  0.8147  11.00000  0.05    0.29
Q15   1   0.5804  0.0145  0.5649  11.00000  0.05    0.27
Q16   1   0.3722  0.3136  0.7342  11.00000  0.05    0.26
Q17   1   0.3375  0.6214  0.7761  11.00000  0.05    0.26
Q18   1   0.3324  0.2530  0.5073  11.00000  0.05    0.26
Q19   1   0.7815  0.3213  0.6846  11.00000  0.05    0.26
Q20   1   0.2960 -0.2917  0.8969  11.00000  0.05    0.26
;
_shelx_res_checksum              19150
####################################################################### 
# 
# 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_25p5GPa
_database_code_depnum_ccdc_archive 'CCDC 2336601'
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_25p5GPa         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.339 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_25p5GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.60 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_PLAT097_AZO_25p5GPa         
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.73 eA-3  
RESPONSE: The residual density is close to the carbon atoms of one phenyl 
ring and, hence, may be an artifact of the lower quality of the high-
pressure data.
;
_vrf_PLAT149_AZO_25p5GPa         
;
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_25p5GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        522 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             2023-03-17
_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                   11.513(11)
_cell_length_b                   5.4804(3)
_cell_length_c                   10.357(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.78(9)
_cell_angle_gamma                90
_cell_volume                     583.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       25500000
_cell_measurement_reflns_used    606
_cell_measurement_theta_min      2.4870
_cell_measurement_theta_max      20.6180

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.075
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.23520
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023) 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         25500000
_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    2.00    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0398523852
_diffrn_orient_matrix_UB_12      0.0053738308
_diffrn_orient_matrix_UB_13      -0.0218572864
_diffrn_orient_matrix_UB_21      0.0027217541
_diffrn_orient_matrix_UB_22      0.0233420010
_diffrn_orient_matrix_UB_23      -0.0360937821
_diffrn_orient_matrix_UB_31      -0.0019691935
_diffrn_orient_matrix_UB_32      -0.0707826713
_diffrn_orient_matrix_UB_33      -0.0134788742
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2373
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_av_R_equivalents  0.0097
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_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         2.269
_diffrn_reflns_theta_max         21.747
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.218
_diffrn_measured_fraction_theta_full 0.339
_diffrn_reflns_Laue_measured_fraction_max 0.218
_diffrn_reflns_Laue_measured_fraction_full 0.339
_diffrn_reflns_point_group_measured_fraction_max 0.218
_diffrn_reflns_point_group_measured_fraction_full 0.339
_reflns_number_total             2373
_reflns_number_gt                1959
_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 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_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 12%. 3 
 low-resolution reflections, that were affected by beamstop, were removed 
 from refinemet ( [-3 1 2] [-1 1 -1] [2 -1 0] ). Some other reflections were 
 removed 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         2373
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0923
_refine_ls_wR_factor_ref         0.3003
_refine_ls_wR_factor_gt          0.2859
_refine_ls_goodness_of_fit_ref   1.335
_refine_ls_restrained_S_all      1.329
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.127
_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(7) 0.1110(4) 0.5086(5) 0.017(2) Uani 1 1 d . U . . .
C1 C 0.4205(9) 0.1427(5) 0.5860(6) 0.018(2) Uani 1 1 d . U . . .
C2 C 0.3796(8) 0.3757(5) 0.5935(6) 0.016(2) Uani 1 1 d . U . . .
H2 H 0.388519 0.501799 0.538545 0.019 Uiso 1 1 calc R U . . .
C3 C 0.3248(8) 0.4151(5) 0.6859(6) 0.020(2) Uani 1 1 d . U . . .
H3 H 0.293279 0.568999 0.691440 0.024 Uiso 1 1 calc R U . . .
C4 C 0.3165(8) 0.2296(6) 0.7689(6) 0.019(2) Uani 1 1 d . U . . .
H4 H 0.281084 0.260992 0.832159 0.023 Uiso 1 1 calc R U . . .
C5 C 0.3587(8) -0.0020(5) 0.7623(5) 0.020(2) Uani 1 1 d . U . . .
H5 H 0.354344 -0.125137 0.821769 0.023 Uiso 1 1 calc R U . . .
C6 C 0.4072(8) -0.0475(5) 0.6666(6) 0.018(2) Uani 1 1 d . U . . .
H6 H 0.431304 -0.205042 0.655409 0.021 Uiso 1 1 calc R U . . .
N2 N 0.9917(7) 0.1116(4) 0.9822(5) 0.019(2) Uani 1 1 d . U . . .
C7 C 0.9214(9) 0.1423(5) 0.8349(6) 0.017(2) Uani 1 1 d . U . . .
C8 C 0.9038(9) -0.0467(6) 0.7395(6) 0.021(2) Uani 1 1 d . U . . .
H8 H 0.927415 -0.204672 0.774185 0.025 Uiso 1 1 calc R U . . .
C9 C 0.8517(8) -0.0021(5) 0.5943(6) 0.019(2) Uani 1 1 d . U . . .
H9 H 0.839875 -0.127186 0.528799 0.022 Uiso 1 1 calc R U . . .
C10 C 0.8176(8) 0.2333(5) 0.5487(6) 0.019(2) Uani 1 1 d . U . . .
H10 H 0.780954 0.267399 0.450291 0.023 Uiso 1 1 calc R U . . .
C11 C 0.8357(9) 0.4201(6) 0.6438(6) 0.021(2) Uani 1 1 d . U . . .
H11 H 0.814094 0.578520 0.608985 0.025 Uiso 1 1 calc R U . . .
C12 C 0.8851(9) 0.3776(5) 0.7887(6) 0.020(2) Uani 1 1 d . U . . .
H12 H 0.893698 0.502379 0.853244 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 0.018(6) 0.0135(14) 0.013(3) 0.0002(10) 0.000(4) 0.0033(15)
C1 0.023(7) 0.0127(12) 0.013(3) 0.0005(12) 0.003(4) 0.0012(17)
C2 0.013(7) 0.0133(13) 0.012(3) 0.0011(11) -0.002(4) 0.0009(17)
C3 0.028(7) 0.0115(13) 0.015(3) -0.0002(11) 0.004(4) 0.0004(17)
C4 0.024(7) 0.0138(13) 0.014(3) 0.0007(12) 0.003(4) 0.0019(18)
C5 0.024(7) 0.0133(14) 0.013(3) 0.0009(11) 0.001(4) 0.0009(18)
C6 0.019(7) 0.0124(12) 0.014(3) -0.0001(12) 0.000(4) 0.0003(17)
N2 0.023(6) 0.0133(14) 0.015(3) 0.0035(10) 0.003(4) 0.0029(15)
C7 0.017(7) 0.0144(13) 0.014(3) 0.0030(11) 0.001(4) 0.0016(17)
C8 0.026(7) 0.0136(12) 0.018(3) 0.0031(12) 0.005(4) 0.0024(18)
C9 0.018(7) 0.0154(14) 0.013(3) 0.0012(12) -0.001(4) 0.0018(18)
C10 0.020(7) 0.0158(14) 0.017(3) -0.0003(12) 0.003(4) 0.0010(18)
C11 0.027(7) 0.0136(13) 0.014(3) 0.0022(12) 0.003(4) 0.0036(18)
C12 0.025(7) 0.0139(14) 0.016(3) 0.0023(12) 0.005(5) 0.0026(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 1.261(5) 3_656 ?
N1 C1 1.383(7) . ?
C1 C2 1.376(5) . ?
C1 C6 1.386(4) . ?
C2 C3 1.380(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.362(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.267(5) 3_757 ?
N2 C7 1.378(8) . ?
C7 C12 1.374(5) . ?
C7 C8 1.381(5) . ?
C8 C9 1.367(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.369(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(5) . ?
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 112.4(4) 3_656 . ?
C2 C1 N1 117.0(3) . . ?
C2 C1 C6 122.0(4) . . ?
N1 C1 C6 120.4(4) . . ?
C1 C2 C3 117.4(3) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 122.1(4) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C6 C5 C4 118.4(3) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2 N2 C7 112.1(5) 3_757 . ?
C12 C7 N2 115.8(4) . . ?
C12 C7 C8 122.1(5) . . ?
N2 C7 C8 121.6(4) . . ?
C9 C8 C7 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 117.6(3) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 H9 121.2 . . ?
C9 C10 C11 122.0(5) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C12 C11 C10 121.1(4) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C7 117.0(3) . . ?
C11 C12 H12 121.5 . . ?
C7 C12 H12 121.5 . . ?

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 -171.1(8) 3_656 . . . ?
N1 N1 C1 C6 16.8(13) 3_656 . . . ?
N1 C1 C2 C3 -171.5(7) . . . . ?
C6 C1 C2 C3 0.4(13) . . . . ?
C1 C2 C3 C4 2.2(12) . . . . ?
C2 C3 C4 C5 -1.5(12) . . . . ?
C3 C4 C5 C6 -1.7(12) . . . . ?
C4 C5 C6 C1 4.2(12) . . . . ?
C2 C1 C6 C5 -3.6(13) . . . . ?
N1 C1 C6 C5 168.1(8) . . . . ?
N2 N2 C7 C12 172.1(8) 3_757 . . . ?
N2 N2 C7 C8 -16.0(11) 3_757 . . . ?
C12 C7 C8 C9 1.7(13) . . . . ?
N2 C7 C8 C9 -169.7(7) . . . . ?
C7 C8 C9 C10 -0.5(12) . . . . ?
C8 C9 C10 C11 0.8(12) . . . . ?
C9 C10 C11 C12 -2.2(12) . . . . ?
C10 C11 C12 C7 3.2(12) . . . . ?
N2 C7 C12 C11 168.9(7) . . . . ?
C8 C7 C12 C11 -2.9(13) . . . . ?


_shelx_res_file                  
;
TITL sample_0179_trans_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 18:41:52 on 28-Feb-2023
REM P2(1)/c (#14 with fixed user cell!)
CELL 0.41000  11.512575   5.480400  10.356873  90.0000 116.7755  90.0000
ZERR    4.00   0.011004   0.000255   0.004416   0.0000   0.0875   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 2
OMIT -1 1 -1
OMIT 2 8 -4
OMIT 2 8 -6
OMIT 2 -1 0
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.200000
BASF   0.12045
FVAR      26.07086
N1    1    0.490899    0.110976    0.508635    11.00000    0.01773    0.01347 =
         0.01254    0.00016   -0.00030    0.00329
C1    2    0.420509    0.142673    0.586002    11.00000    0.02253    0.01274 =
         0.01324    0.00050    0.00278    0.00118
C2    2    0.379580    0.375748    0.593530    11.00000    0.01308    0.01332 =
         0.01182    0.00111   -0.00197    0.00085
AFIX  43
H2    3    0.388519    0.501799    0.538545    11.00000   -1.20000
AFIX   0
C3    2    0.324754    0.415094    0.685868    11.00000    0.02750    0.01148 =
         0.01487   -0.00017    0.00406    0.00037
AFIX  43
H3    3    0.293279    0.568999    0.691440    11.00000   -1.20000
AFIX   0
C4    2    0.316489    0.229602    0.768939    11.00000    0.02444    0.01375 =
         0.01420    0.00072    0.00346    0.00187
AFIX  43
H4    3    0.281084    0.260992    0.832159    11.00000   -1.20000
AFIX   0
C5    2    0.358733   -0.002045    0.762309    11.00000    0.02370    0.01326 =
         0.01346    0.00090    0.00107    0.00092
AFIX  43
H5    3    0.354344   -0.125137    0.821769    11.00000   -1.20000
AFIX   0
C6    2    0.407241   -0.047465    0.666602    11.00000    0.01863    0.01235 =
         0.01355   -0.00008    0.00012    0.00029
AFIX  43
H6    3    0.431304   -0.205042    0.655409    11.00000   -1.20000
AFIX   0
N2    1    0.991732    0.111623    0.982167    11.00000    0.02337    0.01332 =
         0.01519    0.00352    0.00297    0.00293
C7    2    0.921420    0.142257    0.834872    11.00000    0.01708    0.01442 =
         0.01376    0.00305    0.00139    0.00164
C8    2    0.903780   -0.046669    0.739487    11.00000    0.02571    0.01364 =
         0.01765    0.00311    0.00543    0.00235
AFIX  43
H8    3    0.927415   -0.204672    0.774185    11.00000   -1.20000
AFIX   0
C9    2    0.851699   -0.002134    0.594275    11.00000    0.01767    0.01545 =
         0.01332    0.00124   -0.00146    0.00182
AFIX  43
H9    3    0.839875   -0.127186    0.528799    11.00000   -1.20000
AFIX   0
C10   2    0.817573    0.233310    0.548736    11.00000    0.01978    0.01584 =
         0.01682   -0.00033    0.00292    0.00101
AFIX  43
H10   3    0.780954    0.267399    0.450291    11.00000   -1.20000
AFIX   0
C11   2    0.835743    0.420098    0.643788    11.00000    0.02700    0.01362 =
         0.01388    0.00223    0.00260    0.00363
AFIX  43
H11   3    0.814094    0.578520    0.608985    11.00000   -1.20000
AFIX   0
C12   2    0.885064    0.377630    0.788652    11.00000    0.02515    0.01385 =
         0.01627    0.00229    0.00476    0.00264
AFIX  43
H12   3    0.893698    0.502379    0.853244    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0179_trans_bn1 in P2(1)/c
REM wR2 = 0.3003, GooF = S = 1.335, Restrained GooF = 1.329 for all data
REM R1 = 0.0923 for 1959 Fo > 4sig(Fo) and 0.0996 for all 2373 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.2000      0.0000

REM Highest difference peak  0.725,  deepest hole -0.449,  1-sigma level  0.127
Q1    1   0.3487 -0.0057  0.7011  11.00000  0.05    0.73
Q2    1   0.3315  0.4100  0.6300  11.00000  0.05    0.60
Q3    1   0.7903  0.4841  0.6969  11.00000  0.05    0.49
Q4    1   0.9562  0.1352  0.9089  11.00000  0.05    0.47
Q5    1   0.2816 -0.0996  0.6701  11.00000  0.05    0.43
Q6    1   0.7899  0.1007  0.5372  11.00000  0.05    0.42
Q7    1   0.8638  0.4009  0.7204  11.00000  0.05    0.41
Q8    1   0.4075  0.1030  0.8191  11.00000  0.05    0.40
Q9    1   0.3377 -0.0005  0.5403  11.00000  0.05    0.39
Q10   1   0.4443  0.1175  0.5399  11.00000  0.05    0.38
Q11   1   0.2059  0.3745  0.6866  11.00000  0.05    0.36
Q12   1   0.9228  0.2596  0.8274  11.00000  0.05    0.35
Q13   1   0.4461  0.4442  0.5696  11.00000  0.05    0.34
Q14   1   0.2704  0.4853  0.7229  11.00000  0.05    0.34
Q15   1   0.7176  0.1756  0.4355  11.00000  0.05    0.33
Q16   1   0.3696  0.4001  0.5277  11.00000  0.05    0.32
Q17   1   0.3501  0.0378  0.6033  11.00000  0.05    0.32
Q18   1   0.5844  0.2367  0.5784  11.00000  0.05    0.32
Q19   1   0.4027 -0.0088  0.4222  11.00000  0.05    0.32
Q20   1   0.8500  0.0393  0.7645  11.00000  0.05    0.32
;
_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_24p7GPa
_database_code_depnum_ccdc_archive 'CCDC 2336600'
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_24p7GPa         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.336 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_24p7GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.62 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_24p7GPa         
;
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_24p7GPa         
;
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             2023-03-17
_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                   11.550(11)
_cell_length_b                   5.4830(3)
_cell_length_c                   10.377(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.73(8)
_cell_angle_gamma                90
_cell_volume                     586.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       24720000
_cell_measurement_reflns_used    443
_cell_measurement_theta_min      2.4870
_cell_measurement_theta_max      20.5890

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.062
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.15378
_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         24720000
_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    2.00    --    0.00   0.00   0.00  130
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0396596947
_diffrn_orient_matrix_UB_12      0.0055525817
_diffrn_orient_matrix_UB_13      -0.0217572069
_diffrn_orient_matrix_UB_21      0.0027500567
_diffrn_orient_matrix_UB_22      0.0232507507
_diffrn_orient_matrix_UB_23      -0.0360376983
_diffrn_orient_matrix_UB_31      -0.0020719304
_diffrn_orient_matrix_UB_32      -0.0707981536
_diffrn_orient_matrix_UB_33      -0.0134778753
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2286
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_av_R_equivalents  0.0111
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_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         2.264
_diffrn_reflns_theta_max         21.719
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.215
_diffrn_measured_fraction_theta_full 0.336
_diffrn_reflns_Laue_measured_fraction_max 0.215
_diffrn_reflns_Laue_measured_fraction_full 0.336
_diffrn_reflns_point_group_measured_fraction_max 0.215
_diffrn_reflns_point_group_measured_fraction_full 0.336
_reflns_number_total             2286
_reflns_number_gt                1894
_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 12.8%. 
 A low-resolution reflection affected by beamstop [2 -1 0] was removed from 
 refinement. Some other reflections were removed 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         2286
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0866
_refine_ls_wR_factor_ref         0.2812
_refine_ls_wR_factor_gt          0.2686
_refine_ls_goodness_of_fit_ref   1.251
_refine_ls_restrained_S_all      1.238
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.125
_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) 0.1109(4) 0.5086(4) 0.0168(19) Uani 1 1 d . U . . .
C1 C 0.4200(8) 0.1424(5) 0.5857(5) 0.018(2) Uani 1 1 d . U . . .
C2 C 0.3790(8) 0.3752(5) 0.5929(5) 0.016(2) Uani 1 1 d . U . . .
H2 H 0.387063 0.500627 0.537139 0.019 Uiso 1 1 calc R U . . .
C3 C 0.3256(8) 0.4152(5) 0.6860(5) 0.018(2) Uani 1 1 d . U . . .
H3 H 0.295417 0.569658 0.692554 0.022 Uiso 1 1 calc R U . . .
C4 C 0.3169(8) 0.2296(5) 0.7686(5) 0.018(2) Uani 1 1 d . U . . .
H4 H 0.280733 0.260568 0.830949 0.022 Uiso 1 1 calc R U . . .
C5 C 0.3598(8) -0.0016(5) 0.7626(5) 0.017(2) Uani 1 1 d . U . . .
H5 H 0.356423 -0.124235 0.822729 0.021 Uiso 1 1 calc R U . . .
C6 C 0.4075(8) -0.0467(5) 0.6667(5) 0.018(2) Uani 1 1 d . U . . .
H6 H 0.431555 -0.204203 0.655580 0.021 Uiso 1 1 calc R U . . .
N2 N 0.9920(7) 0.1118(4) 0.9821(4) 0.0188(19) Uani 1 1 d . U . . .
C7 C 0.9213(8) 0.1414(5) 0.8348(5) 0.017(2) Uani 1 1 d . U . . .
C8 C 0.9035(8) -0.0479(5) 0.7392(5) 0.019(2) Uani 1 1 d . U . . .
H8 H 0.927134 -0.205885 0.773658 0.022 Uiso 1 1 calc R U . . .
C9 C 0.8513(8) -0.0027(5) 0.5945(5) 0.018(2) Uani 1 1 d . U . . .
H9 H 0.839228 -0.127670 0.529061 0.021 Uiso 1 1 calc R U . . .
C10 C 0.8174(8) 0.2325(5) 0.5489(6) 0.019(2) Uani 1 1 d . U . . .
H10 H 0.781500 0.266577 0.450680 0.023 Uiso 1 1 calc R U . . .
C11 C 0.8347(8) 0.4189(5) 0.6436(5) 0.019(2) Uani 1 1 d . U . . .
H11 H 0.811764 0.576866 0.608793 0.023 Uiso 1 1 calc R U . . .
C12 C 0.8854(8) 0.3762(5) 0.7887(5) 0.020(2) Uani 1 1 d . U . . .
H12 H 0.895022 0.501150 0.853357 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 0.019(6) 0.0133(13) 0.014(3) 0.0007(9) 0.004(4) 0.0032(14)
C1 0.026(6) 0.0120(11) 0.015(3) -0.0001(11) 0.007(4) 0.0000(15)
C2 0.017(6) 0.0128(12) 0.013(3) 0.0004(10) 0.003(4) 0.0011(15)
C3 0.024(6) 0.0122(12) 0.014(3) 0.0000(11) 0.005(4) 0.0008(16)
C4 0.023(6) 0.0138(13) 0.015(3) 0.0007(11) 0.006(4) 0.0019(16)
C5 0.020(6) 0.0135(13) 0.013(3) 0.0009(11) 0.002(4) 0.0001(16)
C6 0.021(6) 0.0124(12) 0.015(3) 0.0007(11) 0.004(4) 0.0013(16)
N2 0.024(6) 0.0136(13) 0.016(3) 0.0030(9) 0.006(4) 0.0025(14)
C7 0.019(6) 0.0138(13) 0.016(3) 0.0024(11) 0.006(4) 0.0009(16)
C8 0.023(6) 0.0135(12) 0.017(3) 0.0023(11) 0.007(4) 0.0012(17)
C9 0.019(6) 0.0147(13) 0.016(3) 0.0005(11) 0.004(4) 0.0006(17)
C10 0.023(6) 0.0150(13) 0.018(3) 0.0002(11) 0.007(4) 0.0009(17)
C11 0.026(6) 0.0127(12) 0.016(3) 0.0017(11) 0.006(4) 0.0025(16)
C12 0.027(7) 0.0128(13) 0.016(3) 0.0013(11) 0.007(4) 0.0020(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 1.262(5) 3_656 ?
N1 C1 1.386(6) . ?
C1 C2 1.375(5) . ?
C1 C6 1.383(4) . ?
C2 C3 1.378(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.360(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.270(5) 3_757 ?
N2 C7 1.381(7) . ?
C7 C12 1.371(5) . ?
C7 C8 1.385(5) . ?
C8 C9 1.366(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.369(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.368(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(4) 3_656 . ?
C2 C1 C6 122.0(3) . . ?
C2 C1 N1 117.0(3) . . ?
C6 C1 N1 120.5(4) . . ?
C1 C2 C3 117.4(3) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 122.0(3) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 118.3(3) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N2 N2 C7 111.9(5) 3_757 . ?
C12 C7 N2 115.6(3) . . ?
C12 C7 C8 122.0(4) . . ?
N2 C7 C8 121.8(4) . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 117.9(3) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 H9 121.1 . . ?
C9 C10 C11 121.9(4) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C7 117.2(3) . . ?
C11 C12 H12 121.4 . . ?
C7 C12 H12 121.4 . . ?

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 -171.2(8) 3_656 . . . ?
N1 N1 C1 C6 17.1(11) 3_656 . . . ?
C6 C1 C2 C3 0.7(12) . . . . ?
N1 C1 C2 C3 -170.7(7) . . . . ?
C1 C2 C3 C4 1.2(12) . . . . ?
C2 C3 C4 C5 -0.2(12) . . . . ?
C3 C4 C5 C6 -2.7(11) . . . . ?
C4 C5 C6 C1 4.5(11) . . . . ?
C2 C1 C6 C5 -3.6(12) . . . . ?
N1 C1 C6 C5 167.5(7) . . . . ?
N2 N2 C7 C12 171.9(7) 3_757 . . . ?
N2 N2 C7 C8 -16.5(10) 3_757 . . . ?
C12 C7 C8 C9 1.4(12) . . . . ?
N2 C7 C8 C9 -169.5(7) . . . . ?
C7 C8 C9 C10 -0.4(11) . . . . ?
C8 C9 C10 C11 0.2(11) . . . . ?
C9 C10 C11 C12 -1.0(11) . . . . ?
C10 C11 C12 C7 2.0(11) . . . . ?
N2 C7 C12 C11 169.3(7) . . . . ?
C8 C7 C12 C11 -2.2(12) . . . . ?


_shelx_res_file                  
;
TITL sample_0177_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 16:55:50 on 28-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  11.550169   5.483016  10.376749  90.0000 116.7283  90.0000
ZERR    4.00   0.010812   0.000265   0.004216   0.0000   0.0848   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 13 0 -12
OMIT -2 7 0
OMIT 2 8 -4
OMIT 2 8 -6
OMIT 2 -1 0
OMIT -1 8 5
OMIT -2 8 6
OMIT -2 8 4
OMIT 0 4 6
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.200000
BASF   0.12776
FVAR      25.44982
N1    1    0.490593    0.110886    0.508555    11.00000    0.01938    0.01329 =
         0.01369    0.00068    0.00382    0.00319
C1    2    0.420010    0.142426    0.585669    11.00000    0.02579    0.01200 =
         0.01481   -0.00014    0.00749   -0.00002
C2    2    0.379047    0.375156    0.592904    11.00000    0.01674    0.01277 =
         0.01342    0.00043    0.00274    0.00106
AFIX  43
H2    3    0.387063    0.500627    0.537139    11.00000   -1.20000
AFIX   0
C3    2    0.325649    0.415218    0.686018    11.00000    0.02354    0.01222 =
         0.01425   -0.00001    0.00499    0.00080
AFIX  43
H3    3    0.295417    0.569658    0.692554    11.00000   -1.20000
AFIX   0
C4    2    0.316909    0.229602    0.768615    11.00000    0.02310    0.01382 =
         0.01450    0.00074    0.00620    0.00195
AFIX  43
H4    3    0.280733    0.260568    0.830949    11.00000   -1.20000
AFIX   0
C5    2    0.359840   -0.001562    0.762640    11.00000    0.01981    0.01353 =
         0.01328    0.00089    0.00245    0.00013
AFIX  43
H5    3    0.356423   -0.124235    0.822729    11.00000   -1.20000
AFIX   0
C6    2    0.407483   -0.046734    0.666691    11.00000    0.02074    0.01237 =
         0.01497    0.00069    0.00391    0.00129
AFIX  43
H6    3    0.431555   -0.204203    0.655580    11.00000   -1.20000
AFIX   0
N2    1    0.991989    0.111809    0.982088    11.00000    0.02386    0.01357 =
         0.01557    0.00302    0.00586    0.00255
C7    2    0.921325    0.141447    0.834755    11.00000    0.01861    0.01383 =
         0.01554    0.00244    0.00578    0.00089
C8    2    0.903524   -0.047884    0.739225    11.00000    0.02304    0.01351 =
         0.01691    0.00228    0.00659    0.00119
AFIX  43
H8    3    0.927134   -0.205885    0.773658    11.00000   -1.20000
AFIX   0
C9    2    0.851321   -0.002675    0.594493    11.00000    0.01880    0.01468 =
         0.01554    0.00054    0.00368    0.00061
AFIX  43
H9    3    0.839228   -0.127670    0.529061    11.00000   -1.20000
AFIX   0
C10   2    0.817383    0.232467    0.548862    11.00000    0.02344    0.01501 =
         0.01775    0.00023    0.00748    0.00090
AFIX  43
H10   3    0.781500    0.266577    0.450680    11.00000   -1.20000
AFIX   0
C11   2    0.834736    0.418883    0.643582    11.00000    0.02607    0.01267 =
         0.01560    0.00167    0.00612    0.00245
AFIX  43
H11   3    0.811764    0.576866    0.608793    11.00000   -1.20000
AFIX   0
C12   2    0.885387    0.376179    0.788699    11.00000    0.02716    0.01276 =
         0.01577    0.00128    0.00690    0.00197
AFIX  43
H12   3    0.895022    0.501150    0.853357    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0177_bn1 in P2(1)/c
REM wR2 = 0.2812, GooF = S = 1.251, Restrained GooF = 1.238 for all data
REM R1 = 0.0866 for 1894 Fo > 4sig(Fo) and 0.0935 for all 2286 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.2000      0.0000

REM Highest difference peak  0.667,  deepest hole -0.536,  1-sigma level  0.125
Q1    1   0.8667 -0.0020  0.6610  11.00000  0.05    0.67
Q2    1   0.3523 -0.0018  0.6982  11.00000  0.05    0.53
Q3    1   0.7966  0.1042  0.5424  11.00000  0.05    0.51
Q4    1   0.9593  0.2629  0.8545  11.00000  0.05    0.48
Q5    1   0.8641  0.3808  0.7224  11.00000  0.05    0.45
Q6    1   0.7758  0.4833  0.6881  11.00000  0.05    0.44
Q7    1   0.9684  0.1166  0.9212  11.00000  0.05    0.44
Q8    1   0.2395  0.2944  0.6826  11.00000  0.05    0.39
Q9    1   0.3121  0.4305  0.6192  11.00000  0.05    0.38
Q10   1   0.8840  0.2519  0.7889  11.00000  0.05    0.37
Q11   1   0.9852  0.0456  0.8190  11.00000  0.05    0.37
Q12   1   0.9428 -0.1091  0.5759  11.00000  0.05    0.36
Q13   1   0.3261  0.2613  0.5269  11.00000  0.05    0.36
Q14   1   0.8738 -0.1769  0.4837  11.00000  0.05    0.35
Q15   1   0.8133  0.6365  0.8777  11.00000  0.05    0.34
Q16   1   0.6908  0.1560  0.4208  11.00000  0.05    0.34
Q17   1   0.4606  0.1365  0.5510  11.00000  0.05    0.33
Q18   1   0.9355  0.0192  1.0280  11.00000  0.05    0.33
Q19   1   0.8350  0.2712  0.8329  11.00000  0.05    0.33
Q20   1   1.0542  0.1864  1.0525  11.00000  0.05    0.33
;
_shelx_res_checksum              41542
####################################################################### 
# 
# 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_22p7GPa
_database_code_depnum_ccdc_archive 'CCDC 2336596'
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_22p7GPa         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.354 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_22p7GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.63 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_22p7GPa         
;
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_22p7GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        498 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             2023-03-17
_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                   11.671(10)
_cell_length_b                   5.4939(2)
_cell_length_c                   10.418(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.47(8)
_cell_angle_gamma                90
_cell_volume                     598.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       22660000
_cell_measurement_reflns_used    504
_cell_measurement_theta_min      2.2520
_cell_measurement_theta_max      20.4960

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.024
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.41187
_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         22660000
_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      -0.0391711991
_diffrn_orient_matrix_UB_12      0.0058037157
_diffrn_orient_matrix_UB_13      -0.0215849537
_diffrn_orient_matrix_UB_21      0.0028495852
_diffrn_orient_matrix_UB_22      0.0229309091
_diffrn_orient_matrix_UB_23      -0.0358644836
_diffrn_orient_matrix_UB_31      -0.0021826776
_diffrn_orient_matrix_UB_32      -0.0707006699
_diffrn_orient_matrix_UB_33      -0.0133425566
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2848
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_av_R_equivalents  0.0111
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_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         2.255
_diffrn_reflns_theta_max         21.644
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.229
_diffrn_measured_fraction_theta_full 0.354
_diffrn_reflns_Laue_measured_fraction_max 0.229
_diffrn_reflns_Laue_measured_fraction_full 0.354
_diffrn_reflns_point_group_measured_fraction_max 0.229
_diffrn_reflns_point_group_measured_fraction_full 0.354
_reflns_number_total             2848
_reflns_number_gt                2381
_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 13.6%. 
 A low-resolution reflection affected by beamstop [2 -1 0] was removed from 
 refinement. Some other reflections were removed 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)+(0.1616P)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         2848
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.2116
_refine_ls_wR_factor_gt          0.2016
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.109
_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 0.4910(5) 0.1109(3) 0.5087(3) 0.0138(16) Uani 1 1 d . U . . .
C1 C 0.4210(6) 0.1424(4) 0.5857(4) 0.0143(16) Uani 1 1 d . U . . .
C2 C 0.3798(6) 0.3748(4) 0.5928(4) 0.0140(17) Uani 1 1 d . U . . .
H2 H 0.388613 0.500246 0.537916 0.017 Uiso 1 1 calc R U . . .
C3 C 0.3250(6) 0.4154(4) 0.6841(4) 0.0154(17) Uani 1 1 d . U . . .
H3 H 0.293742 0.568939 0.689128 0.018 Uiso 1 1 calc R U . . .
C4 C 0.3167(6) 0.2298(4) 0.7671(4) 0.0151(17) Uani 1 1 d . U . . .
H4 H 0.280413 0.260338 0.828899 0.018 Uiso 1 1 calc R U . . .
C5 C 0.3605(6) -0.0001(4) 0.7619(4) 0.0148(17) Uani 1 1 d . U . . .
H5 H 0.357444 -0.122125 0.822223 0.018 Uiso 1 1 calc R U . . .
C6 C 0.4085(6) -0.0462(4) 0.6668(4) 0.0145(17) Uani 1 1 d . U . . .
H6 H 0.432705 -0.203341 0.656415 0.017 Uiso 1 1 calc R U . . .
N2 N 0.9916(5) 0.1105(3) 0.9815(4) 0.0156(16) Uani 1 1 d . U . . .
C7 C 0.9216(6) 0.1390(4) 0.8348(4) 0.0136(17) Uani 1 1 d . U . . .
C8 C 0.9051(6) -0.0513(4) 0.7402(4) 0.0169(17) Uani 1 1 d . U . . .
H8 H 0.929248 -0.208664 0.774565 0.020 Uiso 1 1 calc R U . . .
C9 C 0.8533(6) -0.0055(4) 0.5966(4) 0.0141(18) Uani 1 1 d . U . . .
H9 H 0.842428 -0.129906 0.531633 0.017 Uiso 1 1 calc R U . . .
C10 C 0.8177(6) 0.2283(4) 0.5504(4) 0.0165(17) Uani 1 1 d . U . . .
H10 H 0.782085 0.261473 0.452742 0.020 Uiso 1 1 calc R U . . .
C11 C 0.8331(6) 0.4146(4) 0.6440(4) 0.0151(17) Uani 1 1 d . U . . .
H11 H 0.808142 0.571407 0.609108 0.018 Uiso 1 1 calc R U . . .
C12 C 0.8850(6) 0.3721(4) 0.7887(4) 0.0154(18) Uani 1 1 d . U . . .
H12 H 0.894923 0.497053 0.853029 0.018 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 0.010(5) 0.0155(10) 0.011(2) -0.0001(8) 0.001(3) 0.0025(11)
C1 0.014(5) 0.0142(9) 0.012(2) -0.0004(8) 0.004(3) 0.0002(12)
C2 0.011(5) 0.0148(10) 0.012(2) 0.0000(8) 0.002(3) 0.0004(12)
C3 0.016(5) 0.0135(10) 0.013(2) -0.0001(8) 0.003(3) 0.0014(13)
C4 0.014(5) 0.0158(10) 0.014(2) 0.0004(9) 0.004(3) 0.0018(13)
C5 0.011(5) 0.0148(10) 0.014(2) 0.0011(9) 0.002(3) 0.0007(13)
C6 0.012(5) 0.0140(9) 0.014(2) 0.0002(9) 0.002(3) 0.0003(13)
N2 0.015(5) 0.0150(10) 0.014(2) 0.0022(8) 0.004(3) 0.0021(11)
C7 0.011(5) 0.0148(10) 0.012(2) 0.0014(8) 0.002(3) 0.0006(12)
C8 0.019(5) 0.0135(9) 0.016(2) 0.0016(9) 0.007(3) 0.0001(13)
C9 0.009(6) 0.0153(10) 0.014(2) -0.0003(9) 0.001(4) -0.0003(13)
C10 0.016(5) 0.0161(10) 0.015(2) 0.0010(9) 0.005(3) 0.0001(14)
C11 0.014(5) 0.0141(10) 0.013(2) 0.0013(9) 0.002(3) 0.0013(13)
C12 0.014(6) 0.0145(10) 0.014(2) 0.0010(9) 0.004(4) 0.0011(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 1.387(4) . ?
C1 C2 1.378(4) . ?
C1 C6 1.386(3) . ?
C2 C3 1.380(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.361(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.262(4) 3_757 ?
N2 C7 1.383(6) . ?
C7 C12 1.368(4) . ?
C7 C8 1.390(4) . ?
C8 C9 1.364(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.369(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(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 112.4(3) 3_656 . ?
C2 C1 C6 121.7(3) . . ?
C2 C1 N1 117.2(2) . . ?
C6 C1 N1 120.6(3) . . ?
C1 C2 C3 117.8(2) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 121.9(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 118.7(2) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C1 119.7(2) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2 N2 C7 112.4(4) 3_757 . ?
C12 C7 N2 115.6(3) . . ?
C12 C7 C8 122.2(3) . . ?
N2 C7 C8 121.6(3) . . ?
C9 C8 C7 119.5(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 118.4(2) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C11 C10 C9 121.9(3) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 120.6(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C7 C12 C11 117.5(2) . . ?
C7 C12 H12 121.3 . . ?
C11 C12 H12 121.3 . . ?

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 -170.8(6) 3_656 . . . ?
N1 N1 C1 C6 17.5(9) 3_656 . . . ?
C6 C1 C2 C3 0.0(9) . . . . ?
N1 C1 C2 C3 -171.6(5) . . . . ?
C1 C2 C3 C4 2.1(9) . . . . ?
C2 C3 C4 C5 -0.7(9) . . . . ?
C3 C4 C5 C6 -2.8(9) . . . . ?
C4 C5 C6 C1 4.8(8) . . . . ?
C2 C1 C6 C5 -3.5(9) . . . . ?
N1 C1 C6 C5 167.8(5) . . . . ?
N2 N2 C7 C12 171.6(5) 3_757 . . . ?
N2 N2 C7 C8 -16.9(8) 3_757 . . . ?
C12 C7 C8 C9 1.4(9) . . . . ?
N2 C7 C8 C9 -169.6(5) . . . . ?
C7 C8 C9 C10 -0.8(8) . . . . ?
C8 C9 C10 C11 0.2(8) . . . . ?
C9 C10 C11 C12 -0.2(8) . . . . ?
N2 C7 C12 C11 170.1(5) . . . . ?
C8 C7 C12 C11 -1.4(9) . . . . ?
C10 C11 C12 C7 0.8(8) . . . . ?


_shelx_res_file                  
;
TITL sample_0169_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 16:12:36 on 28-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  11.671112   5.493906  10.418206  90.0000 116.4669  90.0000
ZERR    4.00   0.009925   0.000235   0.003935   0.0000   0.0774   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 13 0 -12
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 0.005
FMAP 2
PLAN 20
WGHT    0.161600
BASF   0.13575
FVAR      24.65630
N1    1    0.490954    0.110917    0.508668    11.00000    0.01017    0.01550 =
         0.01127   -0.00014    0.00071    0.00252
C1    2    0.421031    0.142381    0.585670    11.00000    0.01423    0.01425 =
         0.01213   -0.00041    0.00382    0.00024
C2    2    0.379803    0.374830    0.592817    11.00000    0.01113    0.01479 =
         0.01204    0.00004    0.00163    0.00042
AFIX  43
H2    3    0.388613    0.500246    0.537916    11.00000   -1.20000
AFIX   0
C3    2    0.325035    0.415395    0.684074    11.00000    0.01629    0.01347 =
         0.01250   -0.00007    0.00293    0.00142
AFIX  43
H3    3    0.293742    0.568939    0.689128    11.00000   -1.20000
AFIX   0
C4    2    0.316740    0.229808    0.767149    11.00000    0.01366    0.01583 =
         0.01373    0.00040    0.00413    0.00179
AFIX  43
H4    3    0.280413    0.260338    0.828899    11.00000   -1.20000
AFIX   0
C5    2    0.360505   -0.000126    0.761944    11.00000    0.01133    0.01483 =
         0.01372    0.00107    0.00153    0.00069
AFIX  43
H5    3    0.357444   -0.122125    0.822223    11.00000   -1.20000
AFIX   0
C6    2    0.408480   -0.046152    0.666843    11.00000    0.01213    0.01400 =
         0.01358    0.00022    0.00224    0.00027
AFIX  43
H6    3    0.432705   -0.203341    0.656415    11.00000   -1.20000
AFIX   0
N2    1    0.991608    0.110457    0.981462    11.00000    0.01508    0.01496 =
         0.01441    0.00220    0.00449    0.00215
C7    2    0.921579    0.138996    0.834814    11.00000    0.01119    0.01481 =
         0.01182    0.00139    0.00235    0.00060
C8    2    0.905123   -0.051307    0.740214    11.00000    0.01921    0.01353 =
         0.01648    0.00164    0.00659    0.00007
AFIX  43
H8    3    0.929248   -0.208664    0.774565    11.00000   -1.20000
AFIX   0
C9    2    0.853310   -0.005462    0.596589    11.00000    0.00883    0.01525 =
         0.01364   -0.00026    0.00081   -0.00033
AFIX  43
H9    3    0.842428   -0.129906    0.531633    11.00000   -1.20000
AFIX   0
C10   2    0.817725    0.228316    0.550444    11.00000    0.01578    0.01609 =
         0.01540    0.00101    0.00486    0.00007
AFIX  43
H10   3    0.782085    0.261473    0.452742    11.00000   -1.20000
AFIX   0
C11   2    0.833109    0.414589    0.644002    11.00000    0.01391    0.01407 =
         0.01332    0.00134    0.00239    0.00128
AFIX  43
H11   3    0.808142    0.571407    0.609108    11.00000   -1.20000
AFIX   0
C12   2    0.884988    0.372088    0.788683    11.00000    0.01438    0.01446 =
         0.01433    0.00104    0.00365    0.00111
AFIX  43
H12   3    0.894923    0.497053    0.853029    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0169_bn1 in P2(1)/c
REM wR2 = 0.2116, GooF = S = 1.117, Restrained GooF = 1.103 for all data
REM R1 = 0.0658 for 2381 Fo > 4sig(Fo) and 0.0732 for all 2848 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.1616      0.0000

REM Highest difference peak  0.460,  deepest hole -0.445,  1-sigma level  0.109
Q1    1   0.3513  0.0118  0.6975  11.00000  0.05    0.46
Q2    1   0.8761  0.2475  0.7934  11.00000  0.05    0.45
Q3    1   0.8608 -0.0272  0.6578  11.00000  0.05    0.40
Q4    1   0.3335  0.4038  0.6304  11.00000  0.05    0.40
Q5    1   0.8494  0.3461  0.6111  11.00000  0.05    0.40
Q6    1   0.8629  0.3745  0.7189  11.00000  0.05    0.39
Q7    1   0.7875  0.4819  0.6974  11.00000  0.05    0.38
Q8    1   0.3526 -0.0069  0.5654  11.00000  0.05    0.37
Q9    1   0.4684  0.0913  0.5526  11.00000  0.05    0.35
Q10   1   0.3732  0.3215  0.7362  11.00000  0.05    0.35
Q11   1   0.9510  0.0255  1.0379  11.00000  0.05    0.35
Q12   1   0.2888  0.1063  0.7260  11.00000  0.05    0.34
Q13   1   0.9373 -0.0171  0.9507  11.00000  0.05    0.33
Q14   1   0.9660  0.1152  0.9092  11.00000  0.05    0.31
Q15   1   0.3196  0.2666  0.4883  11.00000  0.05    0.31
Q16   1   0.4729  0.0333  0.6304  11.00000  0.05    0.30
Q17   1   0.4555  0.2517  0.6482  11.00000  0.05    0.30
Q18   1   0.8373  0.3146  0.4768  11.00000  0.05    0.29
Q19   1   0.7807  0.1013  0.5398  11.00000  0.05    0.27
Q20   1   0.7577  0.5219  0.5971  11.00000  0.05    0.27
;
_shelx_res_checksum              40141
####################################################################### 
# 
# 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_24p1GPa
_database_code_depnum_ccdc_archive 'CCDC 2336599'
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_24p1GPa         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.345 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_24p1GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.62 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_24p1GPa         
;
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_24p1GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        509 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             2023-03-17
_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                   11.592(9)
_cell_length_b                   5.4837(2)
_cell_length_c                   10.385(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.64(7)
_cell_angle_gamma                90
_cell_volume                     590.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       24110000
_cell_measurement_reflns_used    473
_cell_measurement_theta_min      2.4870
_cell_measurement_theta_max      20.5660

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.051
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.38698
_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         24110000
_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      -0.0395082264
_diffrn_orient_matrix_UB_12      0.0056405142
_diffrn_orient_matrix_UB_13      -0.0217005204
_diffrn_orient_matrix_UB_21      0.0027608210
_diffrn_orient_matrix_UB_22      0.0231711567
_diffrn_orient_matrix_UB_23      -0.0360027609
_diffrn_orient_matrix_UB_31      -0.0021233225
_diffrn_orient_matrix_UB_32      -0.0707772409
_diffrn_orient_matrix_UB_33      -0.0134492612
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2705
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_av_R_equivalents  0.0115
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_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         2.263
_diffrn_reflns_theta_max         21.707
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.223
_diffrn_measured_fraction_theta_full 0.345
_diffrn_reflns_Laue_measured_fraction_max 0.223
_diffrn_reflns_Laue_measured_fraction_full 0.345
_diffrn_reflns_point_group_measured_fraction_max 0.223
_diffrn_reflns_point_group_measured_fraction_full 0.345
_reflns_number_total             2705
_reflns_number_gt                2201
_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 14.6%. 
 2 low-resolution reflections, that were affected by beamstop, were removed 
 from refinemet ( [-1 1 -1] [2 -1 0] ). Some other reflections were removed 
 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)+(0.1589P)²+0.0086P] 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         2705
_refine_ls_number_parameters     129
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0675
_refine_ls_wR_factor_ref         0.2147
_refine_ls_wR_factor_gt          0.2059
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.104
_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(6) 0.1114(4) 0.5087(4) 0.0152(17) Uani 1 1 d . U . . .
C1 C 0.4207(7) 0.1429(4) 0.5859(5) 0.0140(18) Uani 1 1 d . U . . .
C2 C 0.3797(7) 0.3756(4) 0.5933(5) 0.0141(19) Uani 1 1 d . U . . .
H2 H 0.388662 0.501359 0.538327 0.017 Uiso 1 1 calc R U . . .
C3 C 0.3249(7) 0.4157(4) 0.6851(5) 0.0167(19) Uani 1 1 d . U . . .
H3 H 0.293557 0.569483 0.690462 0.020 Uiso 1 1 calc R U . . .
C4 C 0.3167(7) 0.2298(5) 0.7682(5) 0.0161(18) Uani 1 1 d . U . . .
H4 H 0.280401 0.260369 0.830373 0.019 Uiso 1 1 calc R U . . .
C5 C 0.3603(6) -0.0007(4) 0.7626(4) 0.0158(19) Uani 1 1 d . U . . .
H5 H 0.357313 -0.123219 0.822934 0.019 Uiso 1 1 calc R U . . .
C6 C 0.4081(7) -0.0463(4) 0.6670(5) 0.0155(18) Uani 1 1 d . U . . .
H6 H 0.432238 -0.203750 0.656134 0.019 Uiso 1 1 calc R U . . .
N2 N 0.9919(6) 0.1108(4) 0.9818(4) 0.0170(18) Uani 1 1 d . U . . .
C7 C 0.9215(6) 0.1405(4) 0.8347(4) 0.0145(18) Uani 1 1 d . U . . .
C8 C 0.9043(7) -0.0499(5) 0.7395(5) 0.0177(19) Uani 1 1 d . U . . .
H8 H 0.928149 -0.207773 0.773968 0.021 Uiso 1 1 calc R U . . .
C9 C 0.8523(6) -0.0039(4) 0.5952(4) 0.016(2) Uani 1 1 d . U . . .
H9 H 0.840667 -0.128577 0.529749 0.019 Uiso 1 1 calc R U . . .
C10 C 0.8178(7) 0.2302(4) 0.5497(5) 0.0178(19) Uani 1 1 d . U . . .
H10 H 0.782193 0.263886 0.451578 0.021 Uiso 1 1 calc R U . . .
C11 C 0.8339(7) 0.4169(4) 0.6435(5) 0.0168(19) Uani 1 1 d . U . . .
H11 H 0.809909 0.574426 0.608471 0.020 Uiso 1 1 calc R U . . .
C12 C 0.8849(7) 0.3744(4) 0.7885(5) 0.017(2) Uani 1 1 d . U . . .
H12 H 0.894222 0.499307 0.853007 0.020 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(5) 0.0139(11) 0.013(2) 0.0000(8) 0.004(3) 0.0028(12)
C1 0.015(6) 0.0134(10) 0.012(2) -0.0002(10) 0.004(3) 0.0006(14)
C2 0.013(6) 0.0141(11) 0.012(2) 0.0007(9) 0.003(4) 0.0014(14)
C3 0.021(6) 0.0124(11) 0.014(2) 0.0001(10) 0.006(4) 0.0015(15)
C4 0.018(6) 0.0150(11) 0.015(2) 0.0005(10) 0.007(4) 0.0021(15)
C5 0.017(6) 0.0139(11) 0.015(2) 0.0011(10) 0.006(4) 0.0007(15)
C6 0.017(6) 0.0130(10) 0.015(2) 0.0002(10) 0.005(3) 0.0009(15)
N2 0.021(6) 0.0143(11) 0.016(2) 0.0029(9) 0.009(3) 0.0025(13)
C7 0.015(6) 0.0141(11) 0.013(2) 0.0019(9) 0.005(4) 0.0009(14)
C8 0.023(6) 0.0131(10) 0.018(2) 0.0016(10) 0.010(4) 0.0004(15)
C9 0.015(6) 0.0146(11) 0.015(3) 0.0000(10) 0.004(4) -0.0003(15)
C10 0.022(6) 0.0151(11) 0.017(2) 0.0009(10) 0.009(4) 0.0009(15)
C11 0.021(6) 0.0132(11) 0.014(2) 0.0015(10) 0.006(4) 0.0015(15)
C12 0.020(6) 0.0139(11) 0.016(2) 0.0015(10) 0.008(4) 0.0019(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 1.266(4) 3_656 ?
N1 C1 1.386(5) . ?
C1 C2 1.375(4) . ?
C1 C6 1.385(4) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.359(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.262(4) 3_757 ?
N2 C7 1.382(6) . ?
C7 C12 1.368(4) . ?
C7 C8 1.389(4) . ?
C8 C9 1.365(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.365(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.368(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.368(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 112.4(3) 3_656 . ?
C2 C1 C6 121.9(3) . . ?
C2 C1 N1 117.1(2) . . ?
C6 C1 N1 120.5(3) . . ?
C1 C2 C3 117.6(2) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 121.9(3) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 118.6(2) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2 N2 C7 112.3(4) 3_757 . ?
C12 C7 N2 115.8(3) . . ?
C12 C7 C8 122.2(4) . . ?
N2 C7 C8 121.5(3) . . ?
C9 C8 C7 119.6(3) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C8 118.1(3) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C9 C10 C11 122.2(4) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
C10 C11 C12 120.7(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C7 C12 C11 117.3(3) . . ?
C7 C12 H12 121.4 . . ?
C11 C12 H12 121.4 . . ?

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 -171.0(7) 3_656 . . . ?
N1 N1 C1 C6 17.3(10) 3_656 . . . ?
C6 C1 C2 C3 0.0(10) . . . . ?
N1 C1 C2 C3 -171.6(6) . . . . ?
C1 C2 C3 C4 2.1(10) . . . . ?
C2 C3 C4 C5 -0.8(10) . . . . ?
C3 C4 C5 C6 -2.8(10) . . . . ?
C4 C5 C6 C1 4.8(9) . . . . ?
C2 C1 C6 C5 -3.5(10) . . . . ?
N1 C1 C6 C5 167.7(6) . . . . ?
N2 N2 C7 C12 171.4(6) 3_757 . . . ?
N2 N2 C7 C8 -16.8(9) 3_757 . . . ?
C12 C7 C8 C9 1.7(10) . . . . ?
N2 C7 C8 C9 -169.6(5) . . . . ?
C7 C8 C9 C10 -0.6(9) . . . . ?
C8 C9 C10 C11 0.0(9) . . . . ?
C9 C10 C11 C12 -0.6(10) . . . . ?
N2 C7 C12 C11 169.5(6) . . . . ?
C8 C7 C12 C11 -2.2(9) . . . . ?
C10 C11 C12 C7 1.6(10) . . . . ?


_shelx_res_file                  
;
TITL sample_0175_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 16:51:31 on 28-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  11.591977   5.483679  10.384944  90.0000 116.6356  90.0000
ZERR    4.00   0.009459   0.000232   0.003767   0.0000   0.0746   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 -3 -1 5
OMIT -3 1 5
OMIT 2 8 -4
OMIT 2 -1 0
OMIT -2 8 4

L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.158900    0.008600
BASF   0.14644
FVAR      24.46980   0.94703
N1    1    0.490877    0.111356    0.508651    11.00000    0.01622    0.01385 =
         0.01310    0.00001    0.00441    0.00282
C1    2    0.420658    0.142933    0.585867    11.00000    0.01494    0.01337 =
         0.01176   -0.00017    0.00432    0.00062
C2    2    0.379735    0.375554    0.593252    11.00000    0.01313    0.01406 =
         0.01249    0.00074    0.00340    0.00141
AFIX  43
H2    3    0.388662    0.501359    0.538327    11.00000   -1.20000
AFIX   0
C3    2    0.324921    0.415655    0.685123    11.00000    0.02120    0.01238 =
         0.01435    0.00005    0.00614    0.00154
AFIX  43
H3    3    0.293557    0.569483    0.690462    11.00000   -1.20000
AFIX   0
C4    2    0.316662    0.229818    0.768205    11.00000    0.01798    0.01503 =
         0.01486    0.00045    0.00703    0.00209
AFIX  43
H4    3    0.280401    0.260369    0.830373    11.00000   -1.20000
AFIX   0
C5    2    0.360344   -0.000738    0.762582    11.00000    0.01686    0.01389 =
         0.01491    0.00106    0.00552    0.00074
AFIX  43
H5    3    0.357313   -0.123219    0.822934    11.00000   -1.20000
AFIX   0
C6    2    0.408105   -0.046287    0.667001    11.00000    0.01711    0.01302 =
         0.01457    0.00024    0.00549    0.00087
AFIX  43
H6    3    0.432238   -0.203750    0.656134    11.00000   -1.20000
AFIX   0
N2    1    0.991947    0.110838    0.981804    11.00000    0.02065    0.01431 =
         0.01626    0.00291    0.00860    0.00250
C7    2    0.921507    0.140517    0.834664    11.00000    0.01469    0.01415 =
         0.01345    0.00191    0.00529    0.00089
C8    2    0.904335   -0.049918    0.739532    11.00000    0.02310    0.01308 =
         0.01761    0.00165    0.00968    0.00045
AFIX  43
H8    3    0.928149   -0.207773    0.773968    11.00000   -1.20000
AFIX   0
C9    2    0.852284   -0.003932    0.595173    11.00000    0.01467    0.01464 =
         0.01476    0.00004    0.00430   -0.00034
AFIX  43
H9    3    0.840667   -0.128577    0.529749    11.00000   -1.20000
AFIX   0
C10   2    0.817797    0.230191    0.549652    11.00000    0.02160    0.01512 =
         0.01692    0.00094    0.00879    0.00088
AFIX  43
H10   3    0.782193    0.263886    0.451578    11.00000   -1.20000
AFIX   0
C11   2    0.833873    0.416932    0.643524    11.00000    0.02096    0.01321 =
         0.01449    0.00148    0.00635    0.00155
AFIX  43
H11   3    0.809909    0.574426    0.608471    11.00000   -1.20000
AFIX   0
C12   2    0.884859    0.374369    0.788488    11.00000    0.01983    0.01393 =
         0.01577    0.00151    0.00781    0.00194
AFIX  43
H12   3    0.894222    0.499307    0.853007    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0175_bn1 in P2(1)/c
REM wR2 = 0.2147, GooF = S = 1.113, Restrained GooF = 1.098 for all data
REM R1 = 0.0675 for 2201 Fo > 4sig(Fo) and 0.0762 for all 2705 data
REM 129 parameters refined using 84 restraints

END

WGHT      0.1589      0.0086

REM Highest difference peak  0.422,  deepest hole -0.405,  1-sigma level  0.104
Q1    1   0.9009  0.2472  0.8008  11.00000  0.05    0.42
Q2    1   0.8645 -0.0128  0.6556  11.00000  0.05    0.41
Q3    1   0.3173  0.4387  0.6191  11.00000  0.05    0.40
Q4    1   0.7999  0.1001  0.5522  11.00000  0.05    0.39
Q5    1   0.8427  0.3541  0.6034  11.00000  0.05    0.39
Q6    1   0.3637 -0.0060  0.6953  11.00000  0.05    0.37
Q7    1   0.4602  0.2484  0.6430  11.00000  0.05    0.35
Q8    1   0.8577  0.3759  0.7134  11.00000  0.05    0.35
Q9    1   0.3652  0.3282  0.7380  11.00000  0.05    0.34
Q10   1   0.3691  0.2763  0.5524  11.00000  0.05    0.31
Q11   1   1.0970  0.2636  1.0676  11.00000  0.05    0.29
Q12   1   0.9305 -0.0052  0.9464  11.00000  0.05    0.29
Q13   1   0.3328 -0.0246  0.5373  11.00000  0.05    0.28
Q14   1   0.9031  0.1292  0.6038  11.00000  0.05    0.27
Q15   1   0.7818  0.4838  0.6976  11.00000  0.05    0.27
Q16   1   0.3768 -0.1936  0.8696  11.00000  0.05    0.27
Q17   1   0.4806  0.0666  0.5664  11.00000  0.05    0.26
Q18   1   0.4519 -0.0020  0.4590  11.00000  0.05    0.26
Q19   1   0.2783  0.1028  0.7227  11.00000  0.05    0.26
Q20   1   0.7301  0.1826  0.5003  11.00000  0.05    0.26
;
_shelx_res_checksum              83257
####################################################################### 
# 
# 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_22p3GPa
_database_code_depnum_ccdc_archive 'CCDC 2336595'
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_22p3GPa         
;
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_22p3GPa         
;
PROBLEM: Short Inter H...H Contact  H3       ..H10      .       1.64 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_22p3GPa         
;
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_22p3GPa         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        516 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                   11.694(10)
_cell_length_b                   5.4975(2)
_cell_length_c                   10.427(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.44(8)
_cell_angle_gamma                90
_cell_volume                     600.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_pressure       22310000
_cell_measurement_reflns_used    498
_cell_measurement_theta_min      2.2480
_cell_measurement_theta_max      20.4750

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.016
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55957
_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         22310000
_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      -0.0390776562
_diffrn_orient_matrix_UB_12      0.0058895433
_diffrn_orient_matrix_UB_13      -0.0215571289
_diffrn_orient_matrix_UB_21      0.0028735231
_diffrn_orient_matrix_UB_22      0.0228706082
_diffrn_orient_matrix_UB_23      -0.0358252653
_diffrn_orient_matrix_UB_31      -0.0022288046
_diffrn_orient_matrix_UB_32      -0.0706631538
_diffrn_orient_matrix_UB_33      -0.0133441204
_diffrn_detector                 HPA
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_reflns_number            2649
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0130
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_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         2.254
_diffrn_reflns_theta_max         21.627
_diffrn_reflns_theta_full        14.241
_diffrn_measured_fraction_theta_max 0.225
_diffrn_measured_fraction_theta_full 0.350
_diffrn_reflns_Laue_measured_fraction_max 0.225
_diffrn_reflns_Laue_measured_fraction_full 0.350
_diffrn_reflns_point_group_measured_fraction_max 0.225
_diffrn_reflns_point_group_measured_fraction_full 0.350
_reflns_number_total             2649
_reflns_number_gt                2132
_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 15.7%. 
 2 low-resolution reflections, that were affected by beamstop, were removed 
 from refinemet ( [2 -1 0] [3 -1 -1] ). Some other reflections were removed 
 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)+(0.1551P)²+0.0259P] 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         2649
_refine_ls_number_parameters     128
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_ref         0.2151
_refine_ls_wR_factor_gt          0.2042
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.103
_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) 0.1108(4) 0.5085(4) 0.0153(17) Uani 1 1 d . U . . .
C1 C 0.4209(7) 0.1425(4) 0.5856(5) 0.0153(18) Uani 1 1 d . U . . .
C2 C 0.3801(7) 0.3747(4) 0.5928(4) 0.0144(19) Uani 1 1 d . U . . .
H2 H 0.389221 0.500005 0.538127 0.017 Uiso 1 1 calc R U . . .
C3 C 0.3253(7) 0.4152(4) 0.6840(4) 0.0157(18) Uani 1 1 d . U . . .
H3 H 0.293879 0.568567 0.688813 0.019 Uiso 1 1 calc R U . . .
C4 C 0.3171(7) 0.2298(5) 0.7672(5) 0.0153(18) Uani 1 1 d . U . . .
H4 H 0.280955 0.260389 0.829018 0.018 Uiso 1 1 calc R U . . .
C5 C 0.3607(6) -0.0001(4) 0.7619(4) 0.0158(19) Uani 1 1 d . U . . .
H5 H 0.357645 -0.122154 0.822094 0.019 Uiso 1 1 calc R U . . .
C6 C 0.4086(7) -0.0457(4) 0.6669(5) 0.0158(18) Uani 1 1 d . U . . .
H6 H 0.432994 -0.202673 0.656552 0.019 Uiso 1 1 calc R U . . .
N2 N 0.9918(6) 0.1104(4) 0.9815(4) 0.0154(17) Uani 1 1 d . U . . .
C7 C 0.9219(6) 0.1386(4) 0.8350(4) 0.0140(18) Uani 1 1 d . U . . .
C8 C 0.9051(7) -0.0520(5) 0.7403(5) 0.0173(19) Uani 1 1 d . U . . .
H8 H 0.928996 -0.209332 0.774525 0.021 Uiso 1 1 calc R U . . .
C9 C 0.8533(6) -0.0058(4) 0.5968(4) 0.0149(19) Uani 1 1 d . U . . .
H9 H 0.842547 -0.130067 0.531865 0.018 Uiso 1 1 calc R U . . .
C10 C 0.8177(7) 0.2275(4) 0.5506(5) 0.0161(19) Uani 1 1 d . U . . .
H10 H 0.782108 0.260585 0.453011 0.019 Uiso 1 1 calc R U . . .
C11 C 0.8329(7) 0.4140(4) 0.6442(5) 0.0148(18) Uani 1 1 d . U . . .
H11 H 0.807631 0.570664 0.609411 0.018 Uiso 1 1 calc R U . . .
C12 C 0.8850(7) 0.3712(4) 0.7887(5) 0.016(2) Uani 1 1 d . U . . .
H12 H 0.894999 0.496069 0.853057 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 0.013(5) 0.0170(11) 0.012(2) -0.0001(8) 0.003(3) 0.0027(13)
C1 0.017(6) 0.0156(10) 0.013(2) -0.0001(9) 0.006(3) 0.0004(14)
C2 0.012(6) 0.0162(11) 0.012(2) 0.0002(9) 0.003(4) 0.0002(14)
C3 0.015(6) 0.0151(11) 0.013(2) 0.0002(10) 0.003(4) 0.0016(15)
C4 0.013(6) 0.0175(11) 0.014(2) -0.0002(10) 0.005(4) 0.0011(15)
C5 0.014(6) 0.0163(11) 0.014(2) 0.0007(10) 0.003(4) -0.0001(15)
C6 0.015(6) 0.0152(10) 0.015(2) -0.0004(10) 0.005(4) -0.0006(15)
N2 0.013(5) 0.0169(11) 0.014(2) 0.0017(9) 0.004(3) 0.0017(12)
C7 0.011(6) 0.0167(11) 0.012(2) 0.0019(9) 0.003(4) 0.0012(14)
C8 0.019(6) 0.0146(10) 0.017(2) 0.0018(10) 0.007(4) 0.0002(15)
C9 0.010(6) 0.0168(11) 0.014(3) -0.0009(10) 0.002(4) -0.0015(15)
C10 0.013(6) 0.0178(11) 0.015(2) 0.0008(10) 0.004(4) -0.0011(15)
C11 0.011(6) 0.0157(11) 0.013(2) 0.0015(10) 0.001(4) 0.0015(15)
C12 0.015(6) 0.0157(11) 0.015(2) 0.0004(10) 0.005(4) 0.0003(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 1.388(5) . ?
C1 C2 1.376(4) . ?
C1 C6 1.385(4) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.361(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.262(4) 3_757 ?
N2 C7 1.384(6) . ?
C7 C12 1.367(4) . ?
C7 C8 1.392(4) . ?
C8 C9 1.365(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.368(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.371(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(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 121.8(3) . . ?
C2 C1 N1 117.1(2) . . ?
C6 C1 N1 120.6(3) . . ?
C1 C2 C3 117.7(2) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 121.8(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 118.6(2) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N2 N2 C7 112.3(4) 3_757 . ?
C12 C7 N2 115.6(3) . . ?
C12 C7 C8 122.1(4) . . ?
N2 C7 C8 121.7(3) . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 118.5(3) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C9 C10 C11 121.9(4) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C7 C12 C11 117.7(3) . . ?
C7 C12 H12 121.2 . . ?
C11 C12 H12 121.2 . . ?

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 -171.2(7) 3_656 . . . ?
N1 N1 C1 C6 17.3(10) 3_656 . . . ?
C6 C1 C2 C3 -0.3(10) . . . . ?
N1 C1 C2 C3 -171.8(6) . . . . ?
C1 C2 C3 C4 2.3(10) . . . . ?
C2 C3 C4 C5 -0.9(10) . . . . ?
C3 C4 C5 C6 -2.7(10) . . . . ?
C4 C5 C6 C1 4.6(10) . . . . ?
C2 C1 C6 C5 -3.2(10) . . . . ?
N1 C1 C6 C5 167.9(6) . . . . ?
N2 N2 C7 C12 171.3(6) 3_757 . . . ?
N2 N2 C7 C8 -16.9(9) 3_757 . . . ?
C12 C7 C8 C9 1.7(10) . . . . ?
N2 C7 C8 C9 -169.6(5) . . . . ?
C7 C8 C9 C10 -1.0(9) . . . . ?
C8 C9 C10 C11 0.2(9) . . . . ?
C9 C10 C11 C12 0.0(9) . . . . ?
N2 C7 C12 C11 170.3(5) . . . . ?
C8 C7 C12 C11 -1.5(10) . . . . ?
C10 C11 C12 C7 0.6(9) . . . . ?


_shelx_res_file                  
;
TITL sample_0167_bn1 in P2(1)/c
    merged.res
    created by SHELXL-2018/3 at 15:50:02 on 28-Feb-2023
REM P2(1)/c (#14 with fixed user cell (not necessary: std = user cell)!)
CELL 0.41000  11.694458   5.497539  10.426787  90.0000 116.4420  90.0000
ZERR    4.00   0.010097   0.000232   0.004077   0.0000   0.0794   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 5
OMIT 2 -1 0
OMIT 3 -1 -1
OMIT -3 -1 5
L.S. 10
BOND
LIST 4
ACTA
CONF
BOND $H
TEMP 25
ISOR 0.005
FMAP 2
PLAN 20
WGHT    0.155100    0.025900
BASF   0.15680
FVAR      25.40047
N1    1    0.490652    0.110812    0.508457    11.00000    0.01309    0.01695 =
         0.01247   -0.00007    0.00272    0.00267
C1    2    0.420909    0.142541    0.585593    11.00000    0.01650    0.01557 =
         0.01284   -0.00011    0.00569    0.00035
C2    2    0.380145    0.374655    0.592791    11.00000    0.01171    0.01621 =
         0.01216    0.00024    0.00262    0.00019
AFIX  43
H2    3    0.389221    0.500005    0.538127    11.00000   -1.20000
AFIX   0
C3    2    0.325284    0.415201    0.683954    11.00000    0.01541    0.01511 =
         0.01262    0.00019    0.00269    0.00156
AFIX  43
H3    3    0.293879    0.568567    0.688813    11.00000   -1.20000
AFIX   0
C4    2    0.317090    0.229754    0.767204    11.00000    0.01287    0.01751 =
         0.01407   -0.00024    0.00466    0.00107
AFIX  43
H4    3    0.280955    0.260389    0.829018    11.00000   -1.20000
AFIX   0
C5    2    0.360734   -0.000115    0.761948    11.00000    0.01358    0.01633 =
         0.01430    0.00071    0.00328   -0.00012
AFIX  43
H5    3    0.357645   -0.122154    0.822094    11.00000   -1.20000
AFIX   0
C6    2    0.408620   -0.045699    0.666880    11.00000    0.01485    0.01524 =
         0.01502   -0.00044    0.00461   -0.00061
AFIX  43
H6    3    0.432994   -0.202673    0.656552    11.00000   -1.20000
AFIX   0
N2    1    0.991798    0.110390    0.981542    11.00000    0.01306    0.01686 =
         0.01354    0.00172    0.00355    0.00172
C7    2    0.921867    0.138618    0.834964    11.00000    0.01117    0.01674 =
         0.01156    0.00186    0.00287    0.00123
C8    2    0.905121   -0.051979    0.740297    11.00000    0.01881    0.01457 =
         0.01720    0.00179    0.00693    0.00017
AFIX  43
H8    3    0.928996   -0.209332    0.774525    11.00000   -1.20000
AFIX   0
C9    2    0.853338   -0.005783    0.596786    11.00000    0.00952    0.01678 =
         0.01421   -0.00090    0.00151   -0.00147
AFIX  43
H9    3    0.842547   -0.130067    0.531865    11.00000   -1.20000
AFIX   0
C10   2    0.817671    0.227538    0.550624    11.00000    0.01294    0.01783 =
         0.01502    0.00078    0.00402   -0.00113
AFIX  43
H10   3    0.782108    0.260585    0.453011    11.00000   -1.20000
AFIX   0
C11   2    0.832877    0.414036    0.644219    11.00000    0.01146    0.01571 =
         0.01278    0.00154    0.00127    0.00154
AFIX  43
H11   3    0.807631    0.570664    0.609411    11.00000   -1.20000
AFIX   0
C12   2    0.885031    0.371220    0.788731    11.00000    0.01549    0.01571 =
         0.01518    0.00036    0.00496    0.00025
AFIX  43
H12   3    0.894999    0.496069    0.853057    11.00000   -1.20000
AFIX   0
HKLF 5




REM  sample_0167_bn1 in P2(1)/c
REM wR2 = 0.2151, GooF = S = 1.113, Restrained GooF = 1.098 for all data
REM R1 = 0.0693 for 2132 Fo > 4sig(Fo) and 0.0791 for all 2649 data
REM 128 parameters refined using 84 restraints

END

WGHT      0.1551      0.0259

REM Highest difference peak  0.437,  deepest hole -0.369,  1-sigma level  0.103
Q1    1   0.8975  0.2544  0.8049  11.00000  0.05    0.39
Q2    1   0.3689  0.3202  0.7377  11.00000  0.05    0.39
Q3    1   0.8677  0.3319  0.6173  11.00000  0.05    0.37
Q4    1   0.8427  0.3189  0.4832  11.00000  0.05    0.36
Q5    1   0.8031  0.1013  0.5494  11.00000  0.05    0.34
Q6    1   0.7174  0.1380  0.4630  11.00000  0.05    0.33
Q7    1   0.8208  0.3190  0.7216  11.00000  0.05    0.32
Q8    1   0.4675  0.2480  0.6449  11.00000  0.05    0.32
Q9    1   0.5599  0.0139  0.5407  11.00000  0.05    0.30
Q10   1   0.3868 -0.0874  0.7118  11.00000  0.05    0.30
Q11   1   0.7907  0.4838  0.6960  11.00000  0.05    0.29
Q12   1   0.9546 -0.0209  0.9571  11.00000  0.05    0.29
Q13   1   0.7583  0.5234  0.5692  11.00000  0.05    0.29
Q14   1   0.2314  0.1405  0.6433  11.00000  0.05    0.28
Q15   1   0.7269  0.1981  0.6194  11.00000  0.05    0.27
Q16   1   0.8408 -0.1892  0.4074  11.00000  0.05    0.27
Q17   1   0.9174  0.2974  0.7386  11.00000  0.05    0.27
Q18   1   0.3502  0.2629  0.5247  11.00000  0.05    0.27
Q19   1   1.0466 -0.0145  0.9641  11.00000  0.05    0.26
Q20   1   0.2705  0.1217  0.7109  11.00000  0.05    0.26
;
_shelx_res_checksum              14453
