# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_r20191214d
_database_code_depnum_ccdc_archive 'CCDC 2009024'
loop_
_audit_author_name
_audit_author_address
'Yang Ye'
;TianJin University
China
;
_audit_update_record             
;
2020-06-10 deposited with the CCDC.	2020-10-27 downloaded from the CCDC.
;
_audit_creation_date             2019-12-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        '4-Aminoazobenzene; 3-Amino-4-methylpyridine'
_chemical_formula_moiety         '2(C6 H8 N2), 2(C12 H11 N3)'
_chemical_formula_sum            'C36 H38 N10'
_chemical_formula_weight         610.76
_chemical_melting_point          352.5
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.8699(2)
_cell_length_b                   36.0925(7)
_cell_length_c                   11.3684(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.524(2)
_cell_angle_gamma                90
_cell_volume                     3226.00(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    24091
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      33.5000
_cell_measurement_theta_min      1.8060
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            28712
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         1.880
_diffrn_ambient_temperature      123.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   1.00    8.00    --  -30.00  45.00   0.00  180
  2  ω   -120.00  60.00   1.00    8.00    --  -30.00  45.00  90.00  180
  3  ω   -120.00  60.00   1.00    8.00    --  -30.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0180892000
_diffrn_orient_matrix_UB_12      0.0165818000
_diffrn_orient_matrix_UB_13      -0.0316026000
_diffrn_orient_matrix_UB_21      0.0043673000
_diffrn_orient_matrix_UB_22      0.0101299000
_diffrn_orient_matrix_UB_23      0.0534993000
_diffrn_orient_matrix_UB_31      0.0883043000
_diffrn_orient_matrix_UB_32      0.0028926000
_diffrn_orient_matrix_UB_33      -0.0063097000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5089
_reflns_number_total             5896
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrystalClear (Rigaku,2008)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         5896
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0613P)²+1.5782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1258
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N3-H3A = N3-H3B
 0.9 with sigma of 0.01
 H3B-H3A
 1.5 with sigma of 0.01
3. Others
 Fixed Sof: N9(0.6) N10(0.6) N9'(0.4) N10'(0.4)
4.a Rotating group:
 N1(H1A,H1B), N5(H5A,H5B), N8(H8A,H8B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26), C28(H28), C29(H29), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
4.c Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.0723(2) 0.46824(4) 0.41060(14) 0.0403(4) Uani 1 1 d . . . . .
H1A H -0.002189 0.479570 0.366078 0.048 Uiso 1 1 d GR . . . .
H1B H 0.032615 0.465079 0.479319 0.048 Uiso 1 1 d GR . . . .
N2 N 0.07347(18) 0.36759(4) 0.36866(12) 0.0340(3) Uani 1 1 d . . . . .
C1 C 0.2670(2) 0.46513(5) 0.20128(16) 0.0434(4) Uani 1 1 d . . . . .
H1C H 0.347223 0.477580 0.256515 0.065 Uiso 1 1 calc GR . . . .
H1D H 0.173223 0.482008 0.179533 0.065 Uiso 1 1 calc GR . . . .
H1E H 0.325623 0.457968 0.130492 0.065 Uiso 1 1 calc GR . . . .
C2 C 0.1976(2) 0.43111(5) 0.25852(14) 0.0302(4) Uani 1 1 d . . . . .
C3 C 0.2203(2) 0.39595(5) 0.21331(14) 0.0339(4) Uani 1 1 d . . . . .
H3 H 0.279422 0.392962 0.142845 0.041 Uiso 1 1 calc R . . . .
C4 C 0.1583(2) 0.36519(5) 0.26920(15) 0.0353(4) Uani 1 1 d . . . . .
H4 H 0.176382 0.341432 0.236026 0.042 Uiso 1 1 calc R . . . .
C5 C 0.0488(2) 0.40151(4) 0.41173(14) 0.0309(4) Uani 1 1 d . . . . .
H5 H -0.012812 0.403550 0.481440 0.037 Uiso 1 1 calc R . . . .
C6 C 0.1070(2) 0.43412(4) 0.36167(14) 0.0285(3) Uani 1 1 d . . . . .
N3 N 0.26771(18) 0.63497(4) 0.28403(12) 0.0342(3) Uani 1 1 d D . . . .
N4 N 0.2708(2) 0.54249(4) 0.41946(14) 0.0422(4) Uani 1 1 d . . . . .
C7 C 0.4779(2) 0.65113(5) 0.49315(17) 0.0448(5) Uani 1 1 d . . . . .
H7A H 0.526483 0.651751 0.573998 0.067 Uiso 1 1 calc GR . . . .
H7B H 0.387082 0.669622 0.484293 0.067 Uiso 1 1 calc GR . . . .
H7C H 0.566946 0.656712 0.438173 0.067 Uiso 1 1 calc GR . . . .
C8 C 0.4065(2) 0.61338(5) 0.46711(14) 0.0327(4) Uani 1 1 d . . . . .
C9 C 0.4315(2) 0.58386(6) 0.54460(16) 0.0416(4) Uani 1 1 d . . . . .
H9 H 0.496023 0.587406 0.616303 0.050 Uiso 1 1 calc R . . . .
C10 C 0.3634(2) 0.54951(6) 0.51832(17) 0.0456(5) Uani 1 1 d . . . . .
H10 H 0.383208 0.529911 0.573003 0.055 Uiso 1 1 calc R . . . .
C11 C 0.2462(2) 0.57078(5) 0.34434(15) 0.0341(4) Uani 1 1 d . . . . .
H11 H 0.181419 0.566194 0.273360 0.041 Uiso 1 1 calc R . . . .
C12 C 0.30933(19) 0.60648(4) 0.36320(14) 0.0285(3) Uani 1 1 d . . . . .
N5 N -0.00988(19) 0.31219(4) 0.55270(13) 0.0364(3) Uani 1 1 d . . . . .
H5A H -0.021081 0.325648 0.488269 0.044 Uiso 1 1 d GR . . . .
H5B H -0.097715 0.315958 0.596497 0.044 Uiso 1 1 d GR . . . .
N6 N 0.03479(16) 0.16216(3) 0.43816(11) 0.0266(3) Uani 1 1 d . . . . .
N7 N 0.11981(16) 0.15372(3) 0.34998(11) 0.0270(3) Uani 1 1 d . . . . .
C13 C -0.04994(19) 0.21084(4) 0.56524(13) 0.0274(3) Uani 1 1 d . . . . .
H13 H -0.090970 0.192277 0.615981 0.033 Uiso 1 1 calc R . . . .
C14 C -0.0642(2) 0.24758(4) 0.59579(13) 0.0279(3) Uani 1 1 d . . . . .
H14 H -0.115770 0.254043 0.666937 0.034 Uiso 1 1 calc R . . . .
C15 C -0.00327(19) 0.27564(4) 0.52297(13) 0.0265(3) Uani 1 1 d . . . . .
C16 C 0.0696(2) 0.26498(4) 0.41696(14) 0.0279(3) Uani 1 1 d . . . . .
H16 H 0.110957 0.283480 0.366082 0.033 Uiso 1 1 calc R . . . .
C17 C 0.08192(19) 0.22836(4) 0.38611(13) 0.0263(3) Uani 1 1 d . . . . .
H17 H 0.129975 0.221818 0.313771 0.032 Uiso 1 1 calc R . . . .
C18 C 0.02399(18) 0.20045(4) 0.46066(13) 0.0244(3) Uani 1 1 d . . . . .
C19 C 0.13190(19) 0.11496(4) 0.32809(13) 0.0261(3) Uani 1 1 d . . . . .
C20 C 0.2096(2) 0.10538(4) 0.22450(14) 0.0318(4) Uani 1 1 d . . . . .
H20 H 0.247122 0.124254 0.173520 0.038 Uiso 1 1 calc R . . . .
C21 C 0.2323(2) 0.06844(5) 0.19547(16) 0.0361(4) Uani 1 1 d . . . . .
H21 H 0.284999 0.062032 0.124678 0.043 Uiso 1 1 calc R . . . .
C22 C 0.1781(2) 0.04094(5) 0.26987(16) 0.0366(4) Uani 1 1 d . . . . .
H22 H 0.193647 0.015612 0.250300 0.044 Uiso 1 1 calc R . . . .
C23 C 0.1009(2) 0.05039(4) 0.37308(15) 0.0347(4) Uani 1 1 d . . . . .
H23 H 0.063896 0.031368 0.423762 0.042 Uiso 1 1 calc R . . . .
C24 C 0.0769(2) 0.08712(4) 0.40332(14) 0.0290(3) Uani 1 1 d . . . . .
H24 H 0.023861 0.093355 0.474130 0.035 Uiso 1 1 calc R . . . .
N8 N 0.47195(17) 0.18959(3) 0.32402(12) 0.0283(3) Uani 1 1 d . . . . .
H8A H 0.502097 0.188679 0.397643 0.034 Uiso 1 1 d GR . . . .
H8B H 0.365857 0.184069 0.314933 0.034 Uiso 1 1 d GR . . . .
C25 C 0.6419(2) 0.28378(5) 0.29599(18) 0.0400(4) Uani 1 1 d . . . . .
H25 H 0.721937 0.299564 0.335914 0.048 Uiso 1 1 calc R . . . .
C26 C 0.6151(2) 0.24889(4) 0.33886(14) 0.0288(3) Uani 1 1 d . . . . .
H26 H 0.677295 0.240706 0.407552 0.035 Uiso 1 1 calc R . . . .
C27 C 0.49693(18) 0.22521(4) 0.28218(13) 0.0227(3) Uani 1 1 d . . . . .
C28 C 0.4086(2) 0.23765(5) 0.18017(14) 0.0321(4) Uani 1 1 d . . . . .
H28 H 0.328998 0.221811 0.140001 0.039 Uiso 1 1 calc R . . . .
C29 C 0.4367(2) 0.27294(6) 0.13759(17) 0.0455(5) Uani 1 1 d . . . . .
H29 H 0.375770 0.281284 0.068607 0.055 Uiso 1 1 calc R . . . .
C30 C 0.5547(3) 0.29643(5) 0.1959(2) 0.0471(5) Uani 1 1 d . . . . .
C31 C 0.6277(2) 0.38524(5) 0.0792(2) 0.0442(5) Uani 1 1 d . . . . .
C32 C 0.5538(2) 0.39995(5) -0.02241(19) 0.0462(5) Uani 1 1 d . . . . .
H32 H 0.482656 0.385003 -0.072631 0.055 Uiso 1 1 calc R . . . .
C33 C 0.5832(2) 0.43634(6) -0.05099(16) 0.0421(4) Uani 1 1 d . . . . .
H33 H 0.531693 0.446538 -0.120884 0.051 Uiso 1 1 calc R . . . .
C34 C 0.6865(2) 0.45799(5) 0.02099(17) 0.0374(4) Uani 1 1 d . . . . .
H34 H 0.704586 0.483256 0.001723 0.045 Uiso 1 1 calc R . . . .
C35 C 0.7639(2) 0.44312(5) 0.12105(17) 0.0413(4) Uani 1 1 d . . . . .
H35 H 0.837691 0.457972 0.169720 0.050 Uiso 1 1 calc R . . . .
C36 C 0.7348(3) 0.40680(5) 0.15086(16) 0.0438(5) Uani 1 1 d . . . . .
H36 H 0.787800 0.396561 0.220177 0.053 Uiso 1 1 calc R . . . .
N9 N 0.6136(4) 0.33482(10) 0.1826(3) 0.0256(7) Uani 0.6 1 d . . P A 1
N10 N 0.5661(3) 0.34693(8) 0.0822(2) 0.0254(5) Uani 0.6 1 d . . P A 1
N9' N 0.5402(5) 0.32768(12) 0.1126(4) 0.0254(7) Uani 0.4 1 d . . P A 2
N10' N 0.6372(6) 0.35109(13) 0.1611(5) 0.0278(11) Uani 0.4 1 d . . P A 2
H3A H 0.217(2) 0.6267(5) 0.2165(12) 0.050(6) Uiso 1 1 d D . . . .
H3B H 0.350(2) 0.6517(5) 0.2722(17) 0.059(6) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 H1A 0.8608 . ?
N1 H1B 0.8616 . ?
N1 C6 1.383(2) . ?
N2 C4 1.341(2) . ?
N2 C5 1.336(2) . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C1 C2 1.503(2) . ?
C2 C3 1.384(2) . ?
C2 C6 1.403(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(2) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.393(2) . ?
N3 C12 1.396(2) . ?
N3 H3A 0.899(9) . ?
N3 H3B 0.903(9) . ?
N4 C10 1.337(2) . ?
N4 C11 1.339(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C8 1.498(2) . ?
C8 C9 1.391(3) . ?
C8 C12 1.401(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.394(2) . ?
N5 H5A 0.8801 . ?
N5 H5B 0.8801 . ?
N5 C15 1.363(2) . ?
N6 N7 1.2667(18) . ?
N6 C18 1.4086(19) . ?
N7 C19 1.4249(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.376(2) . ?
C13 C18 1.398(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.406(2) . ?
C15 C16 1.411(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.372(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.405(2) . ?
C19 C20 1.394(2) . ?
C19 C24 1.400(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.387(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.384(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.387(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.385(2) . ?
C24 H24 0.9500 . ?
N8 H8A 0.8604 . ?
N8 H8B 0.8602 . ?
N8 C27 1.3879(19) . ?
C25 H25 0.9500 . ?
C25 C26 1.370(2) . ?
C25 C30 1.381(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.399(2) . ?
C27 C28 1.400(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.384(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.402(3) . ?
C30 N9 1.471(4) . ?
C30 N9' 1.474(5) . ?
C31 C32 1.377(3) . ?
C31 C36 1.385(3) . ?
C31 N10 1.466(4) . ?
C31 N10' 1.545(6) . ?
C32 H32 0.9500 . ?
C32 C33 1.375(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.372(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.376(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.376(3) . ?
C36 H36 0.9500 . ?
N9 N10 1.263(4) . ?
N9' N10' 1.251(7) . ?

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
H1A N1 H1B 109.4 . . ?
C6 N1 H1A 109.1 . . ?
C6 N1 H1B 109.4 . . ?
C5 N2 C4 117.00(14) . . ?
H1C C1 H1D 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C3 C2 C1 122.20(15) . . ?
C3 C2 C6 117.39(15) . . ?
C6 C2 C1 120.41(15) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.87(15) . . ?
C4 C3 H3 119.6 . . ?
N2 C4 C3 122.40(15) . . ?
N2 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
N2 C5 H5 117.7 . . ?
N2 C5 C6 124.66(15) . . ?
C6 C5 H5 117.7 . . ?
N1 C6 C2 121.43(15) . . ?
N1 C6 C5 120.89(15) . . ?
C5 C6 C2 117.66(15) . . ?
C12 N3 H3A 112.8(12) . . ?
C12 N3 H3B 116.1(13) . . ?
H3A N3 H3B 112.9(13) . . ?
C10 N4 C11 116.72(16) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
C9 C8 C7 122.02(16) . . ?
C9 C8 C12 117.03(16) . . ?
C12 C8 C7 120.94(16) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.61(17) . . ?
C10 C9 H9 119.7 . . ?
N4 C10 C9 123.03(17) . . ?
N4 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
N4 C11 H11 117.8 . . ?
N4 C11 C12 124.48(16) . . ?
C12 C11 H11 117.8 . . ?
N3 C12 C8 121.11(15) . . ?
C11 C12 N3 120.65(15) . . ?
C11 C12 C8 118.12(15) . . ?
H5A N5 H5B 109.5 . . ?
C15 N5 H5A 109.3 . . ?
C15 N5 H5B 109.2 . . ?
N7 N6 C18 114.70(12) . . ?
N6 N7 C19 114.58(12) . . ?
C14 C13 H13 119.5 . . ?
C14 C13 C18 120.98(14) . . ?
C18 C13 H13 119.5 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.78(14) . . ?
C15 C14 H14 119.6 . . ?
N5 C15 C14 122.24(14) . . ?
N5 C15 C16 119.80(14) . . ?
C14 C15 C16 117.95(14) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.12(14) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.53(14) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 N6 116.64(13) . . ?
C13 C18 C17 118.61(14) . . ?
C17 C18 N6 124.74(14) . . ?
C20 C19 N7 115.23(13) . . ?
C20 C19 C24 119.79(15) . . ?
C24 C19 N7 124.96(14) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.36(15) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.84(16) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 119.94(16) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 120.98(15) . . ?
C24 C23 H23 119.5 . . ?
C19 C24 H24 120.5 . . ?
C23 C24 C19 119.10(15) . . ?
C23 C24 H24 120.5 . . ?
H8A N8 H8B 109.4 . . ?
C27 N8 H8A 109.4 . . ?
C27 N8 H8B 109.0 . . ?
C26 C25 H25 119.4 . . ?
C26 C25 C30 121.26(17) . . ?
C30 C25 H25 119.4 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.45(16) . . ?
C27 C26 H26 119.8 . . ?
N8 C27 C26 120.61(14) . . ?
N8 C27 C28 120.56(14) . . ?
C26 C27 C28 118.79(14) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 C27 120.26(16) . . ?
C29 C28 H28 119.9 . . ?
C28 C29 H29 119.9 . . ?
C28 C29 C30 120.27(17) . . ?
C30 C29 H29 119.9 . . ?
C25 C30 C29 118.96(16) . . ?
C25 C30 N9 104.4(2) . . ?
C25 C30 N9' 143.6(2) . . ?
C29 C30 N9 136.6(2) . . ?
C29 C30 N9' 97.4(2) . . ?
C32 C31 C36 120.04(16) . . ?
C32 C31 N10 104.77(19) . . ?
C32 C31 N10' 145.2(3) . . ?
C36 C31 N10 135.2(2) . . ?
C36 C31 N10' 94.7(2) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 C31 119.83(17) . . ?
C33 C32 H32 120.1 . . ?
C32 C33 H33 119.9 . . ?
C34 C33 C32 120.29(17) . . ?
C34 C33 H33 119.9 . . ?
C33 C34 H34 120.0 . . ?
C33 C34 C35 120.01(16) . . ?
C35 C34 H34 120.0 . . ?
C34 C35 H35 119.9 . . ?
C34 C35 C36 120.21(17) . . ?
C36 C35 H35 119.9 . . ?
C31 C36 H36 120.2 . . ?
C35 C36 C31 119.60(17) . . ?
C35 C36 H36 120.2 . . ?
N10 N9 C30 109.7(4) . . ?
N9 N10 C31 105.2(3) . . ?
N10' N9' C30 101.8(5) . . ?
N9' N10' C31 105.1(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
N2 C5 C6 N1 178.46(16) . . . . ?
N2 C5 C6 C2 0.2(3) . . . . ?
C1 C2 C3 C4 178.60(16) . . . . ?
C1 C2 C6 N1 2.9(2) . . . . ?
C1 C2 C6 C5 -178.79(15) . . . . ?
C2 C3 C4 N2 0.2(3) . . . . ?
C3 C2 C6 N1 -177.42(15) . . . . ?
C3 C2 C6 C5 0.9(2) . . . . ?
C4 N2 C5 C6 -1.0(2) . . . . ?
C5 N2 C4 C3 0.8(2) . . . . ?
C6 C2 C3 C4 -1.0(2) . . . . ?
N4 C11 C12 N3 -175.49(16) . . . . ?
N4 C11 C12 C8 0.6(3) . . . . ?
C7 C8 C9 C10 179.69(17) . . . . ?
C7 C8 C12 N3 -3.7(2) . . . . ?
C7 C8 C12 C11 -179.86(16) . . . . ?
C8 C9 C10 N4 -0.3(3) . . . . ?
C9 C8 C12 N3 175.55(15) . . . . ?
C9 C8 C12 C11 -0.6(2) . . . . ?
C10 N4 C11 C12 -0.5(3) . . . . ?
C11 N4 C10 C9 0.3(3) . . . . ?
C12 C8 C9 C10 0.4(3) . . . . ?
N5 C15 C16 C17 178.36(14) . . . . ?
N6 N7 C19 C20 173.55(13) . . . . ?
N6 N7 C19 C24 -8.3(2) . . . . ?
N7 N6 C18 C13 -172.19(13) . . . . ?
N7 N6 C18 C17 7.7(2) . . . . ?
N7 C19 C20 C21 178.36(14) . . . . ?
N7 C19 C24 C23 -178.07(14) . . . . ?
C13 C14 C15 N5 -177.59(15) . . . . ?
C13 C14 C15 C16 1.2(2) . . . . ?
C14 C13 C18 N6 179.13(14) . . . . ?
C14 C13 C18 C17 -0.8(2) . . . . ?
C14 C15 C16 C17 -0.4(2) . . . . ?
C15 C16 C17 C18 -0.9(2) . . . . ?
C16 C17 C18 N6 -178.39(14) . . . . ?
C16 C17 C18 C13 1.5(2) . . . . ?
C18 N6 N7 C19 179.43(12) . . . . ?
C18 C13 C14 C15 -0.6(2) . . . . ?
C19 C20 C21 C22 -0.2(3) . . . . ?
C20 C19 C24 C23 0.0(2) . . . . ?
C20 C21 C22 C23 0.1(3) . . . . ?
C21 C22 C23 C24 0.0(3) . . . . ?
C22 C23 C24 C19 0.0(2) . . . . ?
C24 C19 C20 C21 0.1(2) . . . . ?
N8 C27 C28 C29 -178.67(14) . . . . ?
C25 C26 C27 N8 178.72(14) . . . . ?
C25 C26 C27 C28 0.9(2) . . . . ?
C25 C30 N9 N10 168.0(2) . . . . ?
C25 C30 N9' N10' -7.3(5) . . . . ?
C26 C25 C30 C29 0.1(3) . . . . ?
C26 C25 C30 N9 177.79(18) . . . . ?
C26 C25 C30 N9' -175.0(3) . . . . ?
C26 C27 C28 C29 -0.9(2) . . . . ?
C27 C28 C29 C30 0.4(2) . . . . ?
C28 C29 C30 C25 0.0(3) . . . . ?
C28 C29 C30 N9 -176.8(2) . . . . ?
C28 C29 C30 N9' 177.03(19) . . . . ?
C29 C30 N9 N10 -14.9(4) . . . . ?
C29 C30 N9' N10' 177.1(3) . . . . ?
C30 C25 C26 C27 -0.5(2) . . . . ?
C30 N9 N10 C31 178.84(18) . . . . ?
C30 N9' N10' C31 -179.4(2) . . . . ?
C31 C32 C33 C34 0.3(3) . . . . ?
C32 C31 C36 C35 1.3(3) . . . . ?
C32 C31 N10 N9 -171.1(2) . . . . ?
C32 C31 N10' N9' 2.0(6) . . . . ?
C32 C33 C34 C35 1.3(3) . . . . ?
C33 C34 C35 C36 -1.6(3) . . . . ?
C34 C35 C36 C31 0.3(3) . . . . ?
C36 C31 C32 C33 -1.6(3) . . . . ?
C36 C31 N10 N9 9.3(3) . . . . ?
C36 C31 N10' N9' 177.7(3) . . . . ?
N10 C31 C32 C33 178.74(17) . . . . ?
N10 C31 C36 C35 -179.2(2) . . . . ?
N10' C31 C32 C33 173.5(4) . . . . ?
N10' C31 C36 C35 -175.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.452
_oxdiff_exptl_absorpt_empirical_full_min 0.587
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate/n-heptane'
_chemical_properties_physical    Light-sensitive
_exptl_crystal_preparation       photochromic
####################################################################### 
# 
# 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_r20191214c
_database_code_depnum_ccdc_archive 'CCDC 2009026'
loop_
_audit_author_name
_audit_author_address
'Yang Ye'
;TianJin University
China
;
_audit_update_record             
;
2020-06-10 deposited with the CCDC.	2020-10-27 downloaded from the CCDC.
;
_audit_creation_date             2019-12-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        4-Aminoazobenzene;4,4'-Bipyridine
_chemical_formula_moiety         'C12 H11 N3, C10 H8 N2'
_chemical_formula_sum            'C22 H19 N5'
_chemical_formula_weight         353.42
_chemical_absolute_configuration ad
_chemical_melting_point          398.65
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.5794(4)
_cell_length_b                   5.6975(3)
_cell_length_c                   21.4258(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.914(4)
_cell_angle_gamma                90
_cell_volume                     916.43(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7551
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      33.4660
_cell_measurement_theta_min      2.6910
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8125
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.713
_diffrn_ambient_temperature      123.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   1.00    8.00    --  -30.00  45.00   0.00  180
  2  ω   -120.00  60.00   1.00    8.00    --  -30.00  45.00  90.00  180
  3  ω   -120.00  60.00   1.00    8.00    --  -30.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0190258000
_diffrn_orient_matrix_UB_12      0.0041199000
_diffrn_orient_matrix_UB_13      -0.0333445000
_diffrn_orient_matrix_UB_21      0.0692596000
_diffrn_orient_matrix_UB_22      -0.0818432000
_diffrn_orient_matrix_UB_23      -0.0023574000
_diffrn_orient_matrix_UB_31      -0.0613275000
_diffrn_orient_matrix_UB_32      -0.0937271000
_diffrn_orient_matrix_UB_33      0.0006113000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                3081
_reflns_number_total             3247
_reflns_odcompleteness_completeness 99.20
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrystalClear (Rigaku,2008)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1257 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3247
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0990P)²+0.2684P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1516
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Rigid bond restraints
 N2, C6, N3, C7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.0002
3.a Rotating group:
 N1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.2959(4) 0.0751(6) 0.48241(14) 0.0496(8) Uani 1 1 d . . . . .
H1A H 0.275765 -0.070072 0.489938 0.059 Uiso 1 1 d GR . . . .
H1B H 0.202883 0.135773 0.460840 0.059 Uiso 1 1 d GR . . . .
N2 N 0.4052(4) 0.5559(6) 0.71150(15) 0.0454(7) Uani 1 1 d . U . . .
N3 N 0.5119(4) 0.4685(6) 0.75338(15) 0.0439(7) Uani 1 1 d . U . . .
C1 C 0.2799(5) 0.5185(7) 0.60517(18) 0.0450(9) Uani 1 1 d . . . . .
H1 H 0.221146 0.662366 0.611106 0.054 Uiso 1 1 calc R . . . .
C2 C 0.2486(5) 0.4055(7) 0.54765(18) 0.0433(9) Uani 1 1 d . . . . .
H2 H 0.169312 0.472965 0.514257 0.052 Uiso 1 1 calc R . . . .
C3 C 0.3333(4) 0.1913(6) 0.53819(15) 0.0345(7) Uani 1 1 d . . . . .
C4 C 0.4538(4) 0.0970(7) 0.58698(16) 0.0396(8) Uani 1 1 d . . . . .
H4 H 0.514264 -0.045515 0.580890 0.047 Uiso 1 1 calc R . . . .
C5 C 0.4846(5) 0.2136(7) 0.64469(17) 0.0429(9) Uani 1 1 d . . . . .
H5 H 0.566444 0.150261 0.678021 0.051 Uiso 1 1 calc R . . . .
C6 C 0.3950(5) 0.4248(8) 0.65377(18) 0.0454(8) Uani 1 1 d . U . . .
C7 C 0.5198(4) 0.6026(7) 0.81254(18) 0.0416(8) Uani 1 1 d . U . . .
C8 C 0.6198(4) 0.4955(6) 0.86327(17) 0.0385(8) Uani 1 1 d . . . . .
H8 H 0.675287 0.349112 0.857472 0.046 Uiso 1 1 calc R . . . .
C9 C 0.6405(4) 0.5963(7) 0.92185(17) 0.0400(8) Uani 1 1 d . . . . .
H9 H 0.709540 0.518842 0.956144 0.048 Uiso 1 1 calc R . . . .
C10 C 0.5618(4) 0.8099(7) 0.93152(17) 0.0403(8) Uani 1 1 d . . . . .
H10 H 0.575430 0.878767 0.972287 0.048 Uiso 1 1 calc R . . . .
C11 C 0.4623(5) 0.9228(7) 0.88071(19) 0.0460(9) Uani 1 1 d . . . . .
H11 H 0.409019 1.070504 0.886711 0.055 Uiso 1 1 calc R . . . .
C12 C 0.4408(4) 0.8208(7) 0.82157(18) 0.0444(9) Uani 1 1 d . . . . .
H12 H 0.372587 0.898230 0.787087 0.053 Uiso 1 1 calc R . . . .
N4 N 0.1164(4) 0.3457(6) 0.37218(13) 0.0374(7) Uani 1 1 d . . . . .
N5 N -0.0892(4) 0.8138(5) 0.06187(12) 0.0361(7) Uani 1 1 d . . . . .
C13 C 0.1248(4) 0.3204(6) 0.26099(15) 0.0352(7) Uani 1 1 d . . . . .
H13 H 0.160244 0.233938 0.226900 0.042 Uiso 1 1 calc R . . . .
C14 C 0.1620(4) 0.2360(7) 0.32142(15) 0.0372(8) Uani 1 1 d . . . . .
H14 H 0.223918 0.091041 0.327619 0.045 Uiso 1 1 calc R . . . .
C15 C 0.0307(5) 0.5471(8) 0.36140(16) 0.0447(9) Uani 1 1 d . . . . .
H15 H -0.003032 0.629352 0.396471 0.054 Uiso 1 1 calc R . . . .
C16 C -0.0127(5) 0.6455(7) 0.30222(15) 0.0390(8) Uani 1 1 d . . . . .
H16 H -0.075276 0.790276 0.297553 0.047 Uiso 1 1 calc R . . . .
C17 C 0.0352(4) 0.5323(6) 0.24972(14) 0.0257(6) Uani 1 1 d . . . . .
C18 C -0.0079(4) 0.6317(5) 0.18514(13) 0.0247(6) Uani 1 1 d . . . . .
C19 C -0.0990(4) 0.8420(6) 0.17333(14) 0.0286(7) Uani 1 1 d . . . . .
H19 H -0.135208 0.929684 0.207070 0.034 Uiso 1 1 calc R . . . .
C20 C -0.1366(4) 0.9229(7) 0.11203(14) 0.0327(7) Uani 1 1 d . . . . .
H20 H -0.200541 1.066063 0.105242 0.039 Uiso 1 1 calc R . . . .
C21 C -0.0010(4) 0.6121(7) 0.07326(14) 0.0356(7) Uani 1 1 d . . . . .
H21 H 0.033737 0.529557 0.038409 0.043 Uiso 1 1 calc R . . . .
C22 C 0.0430(4) 0.5160(6) 0.13254(13) 0.0299(7) Uani 1 1 d . . . . .
H22 H 0.107215 0.372603 0.137706 0.036 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 H1A 0.8607 . ?
N1 H1B 0.8605 . ?
N1 C3 1.361(4) . ?
N2 N3 1.228(4) . ?
N2 C6 1.438(5) . ?
N3 C7 1.474(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.382(5) . ?
C1 C6 1.371(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.407(5) . ?
C3 C4 1.397(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.395(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.409(6) . ?
C7 C8 1.379(5) . ?
C7 C12 1.405(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.370(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.393(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(6) . ?
C12 H12 0.9500 . ?
N4 C14 1.340(4) . ?
N4 C15 1.323(5) . ?
N5 C20 1.333(4) . ?
N5 C21 1.335(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.374(4) . ?
C13 C17 1.390(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.384(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(4) . ?
C17 C18 1.489(4) . ?
C18 C19 1.389(4) . ?
C18 C22 1.404(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.384(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C21 C22 1.381(4) . ?
C22 H22 0.9500 . ?

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
H1A N1 H1B 109.5 . . ?
C3 N1 H1A 108.9 . . ?
C3 N1 H1B 109.4 . . ?
N3 N2 C6 111.7(3) . . ?
N2 N3 C7 111.3(3) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C6 C1 C2 120.6(4) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.5(3) . . ?
C3 C2 H2 119.8 . . ?
N1 C3 C2 120.3(3) . . ?
N1 C3 C4 120.4(3) . . ?
C4 C3 C2 119.3(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.3(3) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 N2 113.9(4) . . ?
C1 C6 C5 119.7(4) . . ?
C5 C6 N2 126.4(4) . . ?
C8 C7 N3 113.6(4) . . ?
C8 C7 C12 118.8(4) . . ?
C12 C7 N3 127.6(3) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.2(4) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.1(3) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.3(4) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 119.9(4) . . ?
C11 C12 H12 120.0 . . ?
C15 N4 C14 116.0(3) . . ?
C20 N5 C21 116.0(3) . . ?
C14 C13 H13 120.0 . . ?
C14 C13 C17 120.0(3) . . ?
C17 C13 H13 120.0 . . ?
N4 C14 C13 124.0(3) . . ?
N4 C14 H14 118.0 . . ?
C13 C14 H14 118.0 . . ?
N4 C15 H15 118.0 . . ?
N4 C15 C16 124.1(3) . . ?
C16 C15 H15 118.0 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 119.9(3) . . ?
C17 C16 H16 120.0 . . ?
C13 C17 C18 122.1(3) . . ?
C16 C17 C13 116.0(3) . . ?
C16 C17 C18 121.9(3) . . ?
C19 C18 C17 122.5(2) . . ?
C19 C18 C22 116.3(3) . . ?
C22 C18 C17 121.2(3) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.5(3) . . ?
C20 C19 H19 120.2 . . ?
N5 C20 C19 124.5(3) . . ?
N5 C20 H20 117.7 . . ?
C19 C20 H20 117.7 . . ?
N5 C21 H21 117.9 . . ?
N5 C21 C22 124.1(3) . . ?
C22 C21 H21 117.9 . . ?
C18 C22 H22 120.2 . . ?
C21 C22 C18 119.6(3) . . ?
C21 C22 H22 120.2 . . ?

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 C3 C4 C5 -177.3(3) . . . . ?
N2 N3 C7 C8 172.0(3) . . . . ?
N2 N3 C7 C12 -8.9(5) . . . . ?
N3 N2 C6 C1 -178.8(3) . . . . ?
N3 N2 C6 C5 3.7(5) . . . . ?
N3 C7 C8 C9 -179.9(3) . . . . ?
N3 C7 C12 C11 -179.8(3) . . . . ?
C1 C2 C3 N1 177.0(3) . . . . ?
C1 C2 C3 C4 -1.9(5) . . . . ?
C2 C1 C6 N2 -176.6(3) . . . . ?
C2 C1 C6 C5 1.1(5) . . . . ?
C2 C3 C4 C5 1.6(5) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C4 C5 C6 N2 176.0(3) . . . . ?
C4 C5 C6 C1 -1.4(5) . . . . ?
C6 N2 N3 C7 -179.3(3) . . . . ?
C6 C1 C2 C3 0.5(5) . . . . ?
C7 C8 C9 C10 -0.3(5) . . . . ?
C8 C7 C12 C11 -0.8(5) . . . . ?
C8 C9 C10 C11 -0.6(5) . . . . ?
C9 C10 C11 C12 0.8(5) . . . . ?
C10 C11 C12 C7 -0.1(5) . . . . ?
C12 C7 C8 C9 1.0(5) . . . . ?
N4 C15 C16 C17 -0.5(6) . . . . ?
N5 C21 C22 C18 0.7(5) . . . . ?
C13 C17 C18 C19 179.3(3) . . . . ?
C13 C17 C18 C22 -1.0(4) . . . . ?
C14 N4 C15 C16 0.2(6) . . . . ?
C14 C13 C17 C16 -0.5(5) . . . . ?
C14 C13 C17 C18 179.8(3) . . . . ?
C15 N4 C14 C13 -0.1(5) . . . . ?
C15 C16 C17 C13 0.6(5) . . . . ?
C15 C16 C17 C18 -179.7(3) . . . . ?
C16 C17 C18 C19 -0.3(4) . . . . ?
C16 C17 C18 C22 179.4(3) . . . . ?
C17 C13 C14 N4 0.3(5) . . . . ?
C17 C18 C19 C20 -179.2(3) . . . . ?
C17 C18 C22 C21 179.3(3) . . . . ?
C18 C19 C20 N5 -0.9(5) . . . . ?
C19 C18 C22 C21 -1.0(4) . . . . ?
C20 N5 C21 C22 -0.5(5) . . . . ?
C21 N5 C20 C19 0.6(5) . . . . ?
C22 C18 C19 C20 1.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.382
_oxdiff_exptl_absorpt_empirical_full_min 0.512
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate/n-heptane'
_chemical_properties_physical    Light-sensitive
_exptl_crystal_preparation       photochromic
####################################################################### 
# 
# 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_r20191212c
_database_code_depnum_ccdc_archive 'CCDC 2009027'
loop_
_audit_author_name
_audit_author_address
'Yang Ye'
;TianJin University
China
;
_audit_update_record             
;
2020-06-10 deposited with the CCDC.	2020-10-27 downloaded from the CCDC.
;
_audit_creation_date             2019-12-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        4-Aminoazobenzene;1,2-bis(4-pyridyl)ethane
_chemical_formula_moiety         'C12 H12 N2, C12 H11 N3'
_chemical_formula_sum            'C24 H23 N5'
_chemical_formula_weight         381.47
_chemical_absolute_configuration ad
_chemical_melting_point          412.81
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.7300(6)
_cell_length_b                   5.6677(4)
_cell_length_c                   23.0411(14)
_cell_angle_alpha                90
_cell_angle_beta                 91.233(6)
_cell_angle_gamma                90
_cell_volume                     1009.23(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4054
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.4300
_cell_measurement_theta_min      2.6200
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8899
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.636
_diffrn_ambient_temperature      123.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   1.00    8.00    --  -30.00  45.00   0.00  180
  2  ω   -120.00  60.00   1.00    8.00    --  -30.00  45.00  90.00  180
  3  ω   -120.00  60.00   1.00    8.00    --  -30.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0133856000
_diffrn_orient_matrix_UB_12      0.0472446000
_diffrn_orient_matrix_UB_13      -0.0282397000
_diffrn_orient_matrix_UB_21      0.0857266000
_diffrn_orient_matrix_UB_22      0.0446682000
_diffrn_orient_matrix_UB_23      0.0005823000
_diffrn_orient_matrix_UB_31      0.0298878000
_diffrn_orient_matrix_UB_32      -0.1069734000
_diffrn_orient_matrix_UB_33      -0.0122479000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                2844
_reflns_number_total             3986
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrystalClear (Rigaku,2008)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 938 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3986
_refine_ls_number_restraints     74
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0715
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1189P)²+0.5240P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1964
_refine_ls_wR_factor_ref         0.2223
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2. Rigid bond restraints
 N5, C19
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
 C19, N5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
C7 \\sim C6A \\sim C6 \\sim C7A: within 1.7A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C6A) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N4) \\sim Ueq, Uanis(N5) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4. Others
 Fixed Sof: C6(0.36) H6A(0.36) H6B(0.36) C7A(0.64) H7AA(0.64) H7AB(0.64)
 C6A(0.64) H6AA(0.64) H6AB(0.64) C7(0.36) H7A(0.36) H7B(0.36)
5.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7A(H7AA,H7AB), C6A(H6AA,H6AB), C7(H7A,H7B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23),
  C24(H24)
5.c X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 -0.1069(6) 0.7283(9) 0.94430(17) 0.0388(12) Uani 1 1 d . . . . .
N2 N 0.1155(6) 0.2600(10) 0.56067(16) 0.0387(12) Uani 1 1 d . . . . .
C1 C 0.0077(7) 0.4839(12) 0.8702(2) 0.0415(16) Uani 1 1 d . . . . .
H1 H 0.068415 0.344165 0.860456 0.050 Uiso 1 1 calc R . . . .
C2 C -0.0233(6) 0.5380(10) 0.92759(19) 0.0315(13) Uani 1 1 d . . . . .
H2 H 0.017972 0.431874 0.956642 0.038 Uiso 1 1 calc R . . . .
C3 C -0.1617(6) 0.8770(11) 0.9018(2) 0.0369(13) Uani 1 1 d . . . . .
H3 H -0.219287 1.017862 0.912672 0.044 Uiso 1 1 calc R . . . .
C4 C -0.1387(6) 0.8350(11) 0.8444(2) 0.0362(14) Uani 1 1 d . . . . .
H4 H -0.183036 0.942824 0.816256 0.043 Uiso 1 1 calc R . . . .
C5 C -0.0512(8) 0.6366(12) 0.8270(2) 0.0434(16) Uani 1 1 d . . . . .
C6 C -0.083(2) 0.537(4) 0.7635(7) 0.049(3) Uani 0.36 1 d . U P A 1
H6A H -0.165210 0.403877 0.764114 0.059 Uiso 0.36 1 calc R . P A 1
H6B H -0.131473 0.662153 0.737958 0.059 Uiso 0.36 1 calc R . P A 1
C7A C -0.0085(13) 0.3797(18) 0.7407(3) 0.041(2) Uani 0.64 1 d . U P A 2
H7AA H -0.131084 0.330123 0.742486 0.050 Uiso 0.64 1 calc R . P A 2
H7AB H 0.060550 0.270706 0.765537 0.050 Uiso 0.64 1 calc R . P A 2
C8 C 0.0514(8) 0.3570(14) 0.6778(2) 0.0474(17) Uani 1 1 d . . . . .
C9 C -0.0023(7) 0.5120(11) 0.6333(2) 0.0368(14) Uani 1 1 d . . . . .
H9 H -0.061055 0.654048 0.642440 0.044 Uiso 1 1 calc R . . . .
C10 C 0.0304(6) 0.4572(11) 0.5772(2) 0.0348(13) Uani 1 1 d . . . . .
H10 H -0.008645 0.563355 0.547853 0.042 Uiso 1 1 calc R . . . .
C11 C 0.1665(6) 0.1171(11) 0.6037(2) 0.0330(12) Uani 1 1 d . . . . .
H11 H 0.226680 -0.022658 0.593652 0.040 Uiso 1 1 calc R . . . .
C12 C 0.1387(6) 0.1570(10) 0.6614(2) 0.0333(13) Uani 1 1 d . . . . .
H12 H 0.179215 0.047639 0.689836 0.040 Uiso 1 1 calc R . . . .
N3 N 0.4011(6) 0.1420(10) 0.47647(18) 0.0503(13) Uani 1 1 d . . . . .
H3A H 0.452728 0.008797 0.486034 0.060 Uiso 1 1 calc R . . . .
H3B H 0.342006 0.220054 0.502452 0.060 Uiso 1 1 calc R . . . .
N4 N 0.4529(7) 0.5493(12) 0.2556(2) 0.0610(16) Uani 1 1 d . U . . .
N5 N 0.5572(6) 0.4544(11) 0.2263(2) 0.0529(13) Uani 1 1 d . U . . .
C13 C 0.5208(7) 0.1997(13) 0.3253(2) 0.0473(17) Uani 1 1 d . . . . .
H13 H 0.583257 0.116211 0.296761 0.057 Uiso 1 1 calc R . . . .
C14 C 0.5048(6) 0.1069(13) 0.3804(3) 0.0460(16) Uani 1 1 d . . . . .
H14 H 0.557757 -0.040067 0.389623 0.055 Uiso 1 1 calc R . . . .
C15 C 0.4124(7) 0.2255(12) 0.4227(2) 0.0399(14) Uani 1 1 d . . . . .
C16 C 0.3325(7) 0.4450(12) 0.4074(3) 0.0471(16) Uani 1 1 d . . . . .
H16 H 0.267989 0.529711 0.435162 0.057 Uiso 1 1 calc R . . . .
C17 C 0.3491(8) 0.5312(13) 0.3532(3) 0.0519(17) Uani 1 1 d . . . . .
H17 H 0.292776 0.675373 0.343507 0.062 Uiso 1 1 calc R . . . .
C18 C 0.4431(7) 0.4210(14) 0.3115(3) 0.0513(17) Uani 1 1 d . . . . .
C19 C 0.5623(8) 0.5873(15) 0.1699(3) 0.0556(17) Uani 1 1 d . U . . .
C20 C 0.4849(7) 0.8027(14) 0.1553(3) 0.0558(19) Uani 1 1 d . . . . .
H20 H 0.422107 0.888070 0.183419 0.067 Uiso 1 1 calc R . . . .
C21 C 0.5004(7) 0.8905(14) 0.0997(3) 0.0545(18) Uani 1 1 d . . . . .
H21 H 0.446759 1.036723 0.090211 0.065 Uiso 1 1 calc R . . . .
C22 C 0.5912(6) 0.7732(13) 0.0571(3) 0.0493(16) Uani 1 1 d . . . . .
H22 H 0.600341 0.835320 0.019032 0.059 Uiso 1 1 calc R . . . .
C23 C 0.6684(7) 0.5594(13) 0.0730(3) 0.0503(16) Uani 1 1 d . . . . .
H23 H 0.731132 0.473793 0.044937 0.060 Uiso 1 1 calc R . . . .
C24 C 0.6561(7) 0.4694(13) 0.1282(3) 0.0529(18) Uani 1 1 d . . . . .
H24 H 0.712294 0.325134 0.137863 0.064 Uiso 1 1 calc R . . . .
C6A C 0.0082(13) 0.6235(19) 0.7647(3) 0.043(2) Uani 0.64 1 d . U P A 2
H6AA H -0.062003 0.733105 0.740413 0.051 Uiso 0.64 1 calc R . P A 2
H6AB H 0.130530 0.674293 0.763025 0.051 Uiso 0.64 1 calc R . P A 2
C7 C 0.081(2) 0.460(4) 0.7423(7) 0.047(3) Uani 0.36 1 d . U P A 1
H7A H 0.129750 0.335800 0.768048 0.057 Uiso 0.36 1 calc R . P A 1
H7B H 0.163052 0.593557 0.741641 0.057 Uiso 0.36 1 calc R . P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.319(7) . ?
N1 C3 1.353(7) . ?
N2 C10 1.356(8) . ?
N2 C11 1.334(7) . ?
C1 C2 1.383(6) . ?
C1 C5 1.387(8) . ?
C3 C4 1.360(7) . ?
C4 C5 1.376(9) . ?
C5 C6 1.583(17) . ?
C5 C6A 1.520(8) . ?
C6 C7 1.43(2) . ?
C7A C8 1.538(8) . ?
C7A C6A 1.492(11) . ?
C8 C9 1.405(8) . ?
C8 C12 1.376(9) . ?
C8 C7 1.608(18) . ?
C9 C10 1.358(7) . ?
C11 C12 1.369(6) . ?
N3 C15 1.330(7) . ?
N4 N5 1.190(6) . ?
N4 C18 1.483(9) . ?
N5 C19 1.505(9) . ?
C13 C14 1.383(9) . ?
C13 C18 1.423(10) . ?
C14 C15 1.394(8) . ?
C15 C16 1.430(9) . ?
C16 C17 1.350(8) . ?
C17 C18 1.368(9) . ?
C19 C20 1.397(11) . ?
C19 C24 1.387(9) . ?
C20 C21 1.383(9) . ?
C21 C22 1.387(9) . ?
C22 C23 1.396(10) . ?
C23 C24 1.375(9) . ?

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
C2 N1 C3 116.5(4) . . ?
C11 N2 C10 115.4(4) . . ?
C2 C1 C5 119.1(5) . . ?
N1 C2 C1 123.8(5) . . ?
N1 C3 C4 123.3(5) . . ?
C3 C4 C5 120.1(5) . . ?
C1 C5 C6 118.9(10) . . ?
C1 C5 C6A 123.1(6) . . ?
C4 C5 C1 117.2(4) . . ?
C4 C5 C6 119.6(9) . . ?
C4 C5 C6A 118.4(6) . . ?
C7 C6 C5 107.8(13) . . ?
C6A C7A C8 113.6(7) . . ?
C9 C8 C7A 123.0(6) . . ?
C9 C8 C7 118.7(10) . . ?
C12 C8 C7A 119.1(6) . . ?
C12 C8 C9 117.0(4) . . ?
C12 C8 C7 119.4(9) . . ?
C10 C9 C8 119.5(5) . . ?
N2 C10 C9 123.9(5) . . ?
N2 C11 C12 124.9(5) . . ?
C11 C12 C8 119.3(5) . . ?
N5 N4 C18 108.6(6) . . ?
N4 N5 C19 107.1(5) . . ?
C14 C13 C18 119.6(6) . . ?
C13 C14 C15 121.1(6) . . ?
N3 C15 C14 121.6(6) . . ?
N3 C15 C16 120.2(6) . . ?
C14 C15 C16 118.1(6) . . ?
C17 C16 C15 119.7(6) . . ?
C16 C17 C18 123.2(7) . . ?
C13 C18 N4 126.6(6) . . ?
C17 C18 N4 115.1(6) . . ?
C17 C18 C13 118.3(6) . . ?
C20 C19 N5 128.8(6) . . ?
C24 C19 N5 112.4(7) . . ?
C24 C19 C20 118.9(7) . . ?
C21 C20 C19 119.5(6) . . ?
C20 C21 C22 122.5(7) . . ?
C21 C22 C23 116.8(7) . . ?
C24 C23 C22 121.8(6) . . ?
C23 C24 C19 120.6(7) . . ?
C7A C6A C5 111.7(7) . . ?
C6 C7 C8 108.6(12) . . ?

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 C3 C4 C5 -2.0(9) . . . . ?
N2 C11 C12 C8 0.3(8) . . . . ?
C1 C5 C6 C7 -63.5(17) . . . . ?
C1 C5 C6A C7A 51.0(11) . . . . ?
C2 N1 C3 C4 1.8(8) . . . . ?
C2 C1 C5 C4 -0.2(9) . . . . ?
C2 C1 C5 C6 -156.6(10) . . . . ?
C2 C1 C5 C6A 166.3(7) . . . . ?
C3 N1 C2 C1 -0.9(8) . . . . ?
C3 C4 C5 C1 1.1(8) . . . . ?
C3 C4 C5 C6 157.3(11) . . . . ?
C3 C4 C5 C6A -166.1(6) . . . . ?
C4 C5 C6 C7 140.7(12) . . . . ?
C4 C5 C6A C7A -142.6(7) . . . . ?
C5 C1 C2 N1 0.1(9) . . . . ?
C5 C6 C7 C8 179.7(16) . . . . ?
C7A C8 C9 C10 -168.3(7) . . . . ?
C7A C8 C12 C11 169.0(6) . . . . ?
C8 C7A C6A C5 -179.5(7) . . . . ?
C8 C9 C10 N2 -1.0(9) . . . . ?
C9 C8 C12 C11 -0.9(9) . . . . ?
C9 C8 C7 C6 65.5(16) . . . . ?
C10 N2 C11 C12 0.1(8) . . . . ?
C11 N2 C10 C9 0.3(8) . . . . ?
C12 C8 C9 C10 1.2(9) . . . . ?
C12 C8 C7 C6 -139.8(12) . . . . ?
N3 C15 C16 C17 178.1(5) . . . . ?
N4 N5 C19 C20 9.7(8) . . . . ?
N4 N5 C19 C24 -169.2(5) . . . . ?
N5 N4 C18 C13 -9.9(8) . . . . ?
N5 N4 C18 C17 170.0(5) . . . . ?
N5 C19 C20 C21 -177.5(5) . . . . ?
N5 C19 C24 C23 177.1(6) . . . . ?
C13 C14 C15 N3 -177.7(5) . . . . ?
C13 C14 C15 C16 0.8(8) . . . . ?
C14 C13 C18 N4 177.6(5) . . . . ?
C14 C13 C18 C17 -2.3(8) . . . . ?
C14 C15 C16 C17 -0.4(8) . . . . ?
C15 C16 C17 C18 -1.5(8) . . . . ?
C16 C17 C18 N4 -177.1(5) . . . . ?
C16 C17 C18 C13 2.8(9) . . . . ?
C18 N4 N5 C19 179.4(5) . . . . ?
C18 C13 C14 C15 0.6(8) . . . . ?
C19 C20 C21 C22 -0.3(9) . . . . ?
C20 C19 C24 C23 -1.9(9) . . . . ?
C20 C21 C22 C23 -0.2(8) . . . . ?
C21 C22 C23 C24 -0.3(9) . . . . ?
C22 C23 C24 C19 1.4(9) . . . . ?
C24 C19 C20 C21 1.3(8) . . . . ?
C6A C7A C8 C9 -48.8(11) . . . . ?
C6A C7A C8 C12 141.9(8) . . . . ?
C7 C8 C9 C10 156.6(9) . . . . ?
C7 C8 C12 C11 -156.1(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.376
_oxdiff_exptl_absorpt_empirical_full_min 0.613
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate/n-heptane'
_chemical_properties_physical    Light-sensitive
_exptl_crystal_preparation       photochromic
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 2009056'
loop_
_audit_author_name
_audit_author_address
'Yang Ye'
;TianJin University
China
;
_audit_update_record             
;
2020-06-10 deposited with the CCDC.	2020-10-27 downloaded from the CCDC.
;
_audit_creation_date             2020-06-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        '4-Aminoazobenzene; 4-Pyrrolidinopyridine'
_chemical_formula_moiety         'C12 H11 N3, C9 H12 N2'
_chemical_formula_sum            'C21 H23 N5'
_chemical_formula_weight         345.44
_chemical_absolute_configuration ?
_chemical_melting_point          352.12
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.9177(16)
_cell_length_b                   5.9154(12)
_cell_length_c                   19.843(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.84(3)
_cell_angle_gamma                90
_cell_volume                     929.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2790
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9143
_cell_measurement_theta_min      2.0529
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.7556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11209
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.883
_diffrn_reflns_theta_min         2.053
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3075
_reflns_number_total             4268
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       0.043(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4268
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      0.977
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0606P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1160
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2. Restrained distances
 H1A-H1B
 1.5 with sigma of 0.01
 N1-H1A = N1-H1B
 0.9 with sigma of 0.01
 H19A-H19B = H19C-H19D
 1.55 with sigma of 0.01
 C19-H19A = C19'-H19B = C19-H19C = C19'-H19D
 0.93 with sigma of 0.05
3. Rigid bond restraints
 N2, C4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Fixed Sof: C19(0.5) H19A(0.5) H19B(0.5) C19'(0.5) H19C(0.5) H19D(0.5)
5.a Riding coordinates:
 C18(H18A,H18B), C20(H20A,H20B)
5.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.5579(3) 0.5979(5) 0.55427(13) 0.0455(6) Uani 1 1 d D . . . .
H1A H 0.639(3) 0.560(5) 0.5247(12) 0.055 Uiso 1 1 d DR . . . .
H1B H 0.516(4) 0.736(3) 0.5478(14) 0.055 Uiso 1 1 d DR . . . .
N2 N 0.4643(3) 0.1261(4) 0.79444(11) 0.0367(5) Uani 1 1 d . U . . .
N3 N 0.3620(3) 0.2075(4) 0.83513(12) 0.0402(6) Uani 1 1 d . . . . .
N4 N -0.1903(3) 0.4387(4) 0.45843(11) 0.0362(6) Uani 1 1 d . . . . .
N5 N 0.0496(3) 0.3167(4) 0.27466(11) 0.0305(5) Uani 1 1 d . . . . .
C1 C 0.5374(3) 0.4906(5) 0.61438(13) 0.0322(6) Uani 1 1 d . . . . .
C2 C 0.6138(3) 0.2807(5) 0.62710(14) 0.0341(6) Uani 1 1 d . . . . .
H2 H 0.684328 0.215229 0.594071 0.041 Uiso 1 1 calc R . . . .
C3 C 0.5880(3) 0.1688(5) 0.68660(13) 0.0336(6) Uani 1 1 d . . . . .
H3 H 0.640435 0.026377 0.694192 0.040 Uiso 1 1 calc R . . . .
C4 C 0.4859(3) 0.2614(5) 0.73595(14) 0.0336(6) Uani 1 1 d . U . . .
C5 C 0.4120(3) 0.4736(5) 0.72460(14) 0.0349(6) Uani 1 1 d . . . . .
H5 H 0.343892 0.539733 0.758337 0.042 Uiso 1 1 calc R . . . .
C6 C 0.4371(3) 0.5868(5) 0.66522(13) 0.0333(6) Uani 1 1 d . . . . .
H6 H 0.386649 0.730738 0.658242 0.040 Uiso 1 1 calc R . . . .
C7 C 0.3354(3) 0.0629(5) 0.89345(13) 0.0360(6) Uani 1 1 d . . . . .
C8 C 0.4094(3) -0.1473(6) 0.90411(15) 0.0424(7) Uani 1 1 d . . . . .
H8 H 0.485859 -0.206911 0.872236 0.051 Uiso 1 1 calc R . . . .
C9 C 0.3708(4) -0.2702(6) 0.96173(14) 0.0449(8) Uani 1 1 d . . . . .
H9 H 0.422578 -0.412745 0.969741 0.054 Uiso 1 1 calc R . . . .
C10 C 0.2565(4) -0.1840(6) 1.00735(15) 0.0448(8) Uani 1 1 d . . . . .
H10 H 0.229261 -0.268193 1.046484 0.054 Uiso 1 1 calc R . . . .
C11 C 0.1818(4) 0.0252(5) 0.99598(15) 0.0446(8) Uani 1 1 d . . . . .
H11 H 0.103775 0.084608 1.027277 0.054 Uiso 1 1 calc R . . . .
C12 C 0.2214(3) 0.1454(5) 0.93936(13) 0.0388(7) Uani 1 1 d . . . . .
H12 H 0.169541 0.287980 0.931537 0.047 Uiso 1 1 calc R . . . .
C13 C -0.1014(3) 0.2487(5) 0.44651(14) 0.0371(7) Uani 1 1 d . . . . .
H13 H -0.096952 0.138335 0.481263 0.044 Uiso 1 1 calc R . . . .
C14 C -0.0170(3) 0.2020(5) 0.38837(13) 0.0335(6) Uani 1 1 d . . . . .
H14 H 0.044337 0.064841 0.384129 0.040 Uiso 1 1 calc R . . . .
C15 C -0.0216(3) 0.3585(4) 0.33497(13) 0.0276(6) Uani 1 1 d . . . . .
C16 C -0.1063(3) 0.5621(4) 0.34802(13) 0.0324(6) Uani 1 1 d . . . . .
H16 H -0.108700 0.678909 0.315161 0.039 Uiso 1 1 calc R . . . .
C17 C -0.1859(3) 0.5918(5) 0.40855(13) 0.0349(6) Uani 1 1 d . . . . .
H17 H -0.242080 0.731578 0.415605 0.042 Uiso 1 1 calc R . . . .
C18 C 0.1159(4) 0.0950(5) 0.25564(14) 0.0397(7) Uani 1 1 d . . . . .
H18A H 0.033564 -0.026164 0.265433 0.048 Uiso 1 1 d R . . A .
H18B H 0.223064 0.062466 0.280072 0.048 Uiso 1 1 d R . . . .
C19 C 0.1866(11) 0.1267(18) 0.1869(5) 0.047(2) Uani 0.5 1 d D . P A 1
H19A H 0.209(8) -0.005(11) 0.160(4) 0.056 Uiso 0.5 1 d DR . P B 1
H19B H 0.306(8) 0.195(9) 0.192(3) 0.056 Uiso 0.5 1 d DR . P C 1
C19' C 0.0996(11) 0.1006(17) 0.1784(4) 0.047(2) Uani 0.5 1 d D . P A 2
H19C H 0.157(6) -0.018(15) 0.154(5) 0.056 Uiso 0.5 1 d DR . P D 2
H19D H -0.022(6) 0.081(12) 0.164(3) 0.056 Uiso 0.5 1 d DR . P E 2
C20 C 0.1035(5) 0.3342(6) 0.15910(16) 0.0612(10) Uani 1 1 d . . . . .
H20A H 0.018481 0.325107 0.122098 0.073 Uiso 1 1 d R . . A .
H20B H 0.205911 0.408397 0.141558 0.073 Uiso 1 1 d R . . . .
C21 C 0.0351(4) 0.4686(5) 0.21656(13) 0.0390(7) Uani 1 1 d . . . . .
H21A H 0.102324 0.607716 0.224049 0.047 Uiso 1 1 calc R . . . .
H21B H -0.084134 0.511101 0.207858 0.047 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 H1A 0.905(12) . ?
N1 H1B 0.892(12) . ?
N1 C1 1.363(3) . ?
N2 N3 1.248(3) . ?
N2 C4 1.422(3) . ?
N3 C7 1.457(4) . ?
N4 C13 1.349(3) . ?
N4 C17 1.343(3) . ?
N5 C15 1.353(3) . ?
N5 C18 1.464(4) . ?
N5 C21 1.465(3) . ?
C1 C2 1.402(4) . ?
C1 C6 1.413(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.372(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(4) . ?
C4 C5 1.402(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.372(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(4) . ?
C7 C12 1.381(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.393(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.370(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.370(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.407(3) . ?
C15 C16 1.405(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.376(4) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9901 . ?
C18 H18B 0.9900 . ?
C18 C19 1.493(9) . ?
C18 C19' 1.536(9) . ?
C19 H19A 0.97(5) . ?
C19 H19B 1.03(5) . ?
C19 C20 1.495(10) . ?
C19' H19C 0.97(6) . ?
C19' H19D 1.00(4) . ?
C19' C20 1.435(11) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.497(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?

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
H1A N1 H1B 113.5(19) . . ?
C1 N1 H1A 123.2(18) . . ?
C1 N1 H1B 120.4(17) . . ?
N3 N2 C4 113.4(2) . . ?
N2 N3 C7 113.0(2) . . ?
C17 N4 C13 114.4(2) . . ?
C15 N5 C18 123.2(2) . . ?
C15 N5 C21 123.7(2) . . ?
C18 N5 C21 111.8(2) . . ?
N1 C1 C2 120.9(2) . . ?
N1 C1 C6 120.9(3) . . ?
C2 C1 C6 118.2(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 N2 115.5(2) . . ?
C3 C4 C5 119.0(3) . . ?
C5 C4 N2 125.5(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 H6 119.8 . . ?
C8 C7 N3 125.5(3) . . ?
C12 C7 N3 114.9(3) . . ?
C12 C7 C8 119.6(3) . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.7(3) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.1(3) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C7 C12 H12 119.4 . . ?
C11 C12 C7 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
N4 C13 H13 117.3 . . ?
N4 C13 C14 125.3(3) . . ?
C14 C13 H13 117.3 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
N5 C15 C14 122.6(2) . . ?
N5 C15 C16 121.7(2) . . ?
C16 C15 C14 115.6(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.8(2) . . ?
C17 C16 H16 120.1 . . ?
N4 C17 C16 125.1(3) . . ?
N4 C17 H17 117.5 . . ?
C16 C17 H17 117.5 . . ?
N5 C18 H18A 111.0 . . ?
N5 C18 H18B 110.9 . . ?
N5 C18 C19 105.3(4) . . ?
N5 C18 C19' 102.3(4) . . ?
H18A C18 H18B 109.0 . . ?
C19 C18 H18A 121.8 . . ?
C19 C18 H18B 98.1 . . ?
C19' C18 H18A 99.5 . . ?
C19' C18 H18B 123.5 . . ?
C18 C19 H19A 119(6) . . ?
C18 C19 H19B 108(3) . . ?
C18 C19 C20 105.7(6) . . ?
H19A C19 H19B 101(4) . . ?
C20 C19 H19A 123(6) . . ?
C20 C19 H19B 97(4) . . ?
C18 C19' H19C 117(6) . . ?
C18 C19' H19D 111(3) . . ?
H19C C19' H19D 103(4) . . ?
C20 C19' C18 106.6(6) . . ?
C20 C19' H19C 123(6) . . ?
C20 C19' H19D 93(4) . . ?
C19 C20 H20A 121.3 . . ?
C19 C20 H20B 97.8 . . ?
C19 C20 C21 108.5(4) . . ?
C19' C20 H20A 97.4 . . ?
C19' C20 H20B 122.8 . . ?
C19' C20 C21 107.3(4) . . ?
H20A C20 H20B 108.4 . . ?
C21 C20 H20A 110.2 . . ?
C21 C20 H20B 109.8 . . ?
N5 C21 C20 104.4(2) . . ?
N5 C21 H21A 110.9 . . ?
N5 C21 H21B 110.9 . . ?
C20 C21 H21A 110.9 . . ?
C20 C21 H21B 110.9 . . ?
H21A C21 H21B 108.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A N4 0.905(12) 2.030(12) 2.930(3) 173(3) 1_655 yes
C21 H21B N3 0.99 2.62 3.584(4) 164.6 2_556 yes

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 C1 C2 C3 -177.5(3) . . . . ?
N1 C1 C6 C5 177.5(3) . . . . ?
N2 N3 C7 C8 -1.7(4) . . . . ?
N2 N3 C7 C12 -179.2(2) . . . . ?
N2 C4 C5 C6 -177.9(2) . . . . ?
N3 N2 C4 C3 -174.9(2) . . . . ?
N3 N2 C4 C5 4.2(4) . . . . ?
N3 C7 C8 C9 -178.9(3) . . . . ?
N3 C7 C12 C11 178.8(3) . . . . ?
N4 C13 C14 C15 -0.9(4) . . . . ?
N5 C15 C16 C17 175.9(2) . . . . ?
N5 C18 C19 C20 -20.5(7) . . . . ?
N5 C18 C19' C20 25.5(6) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C1 C6 C5 -1.7(4) . . . . ?
C2 C3 C4 N2 178.0(2) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C3 C4 C5 C6 1.2(4) . . . . ?
C4 N2 N3 C7 177.5(2) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C6 C1 C2 C3 1.8(4) . . . . ?
C7 C8 C9 C10 1.2(4) . . . . ?
C8 C7 C12 C11 1.1(4) . . . . ?
C8 C9 C10 C11 -0.6(5) . . . . ?
C9 C10 C11 C12 0.2(5) . . . . ?
C10 C11 C12 C7 -0.5(5) . . . . ?
C12 C7 C8 C9 -1.5(4) . . . . ?
C13 N4 C17 C16 3.1(4) . . . . ?
C13 C14 C15 N5 -175.6(3) . . . . ?
C13 C14 C15 C16 4.0(4) . . . . ?
C14 C15 C16 C17 -3.6(4) . . . . ?
C15 N5 C18 C19 -178.2(4) . . . . ?
C15 N5 C18 C19' 153.5(4) . . . . ?
C15 N5 C21 C20 -169.5(3) . . . . ?
C15 C16 C17 N4 0.1(4) . . . . ?
C17 N4 C13 C14 -2.6(4) . . . . ?
C18 N5 C15 C14 9.2(4) . . . . ?
C18 N5 C15 C16 -170.4(3) . . . . ?
C18 N5 C21 C20 -2.3(3) . . . . ?
C18 C19 C20 C21 19.8(7) . . . . ?
C18 C19' C20 C21 -28.0(7) . . . . ?
C19 C20 C21 N5 -10.9(5) . . . . ?
C19' C20 C21 N5 19.0(5) . . . . ?
C21 N5 C15 C14 175.0(3) . . . . ?
C21 N5 C15 C16 -4.6(4) . . . . ?
C21 N5 C18 C19 14.5(5) . . . . ?
C21 N5 C18 C19' -13.8(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate/n-heptane'
_chemical_properties_physical    Light-sensitive
_exptl_crystal_preparation       photochromic
####################################################################### 
# 
# 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_r20200101a1
_database_code_depnum_ccdc_archive 'CCDC 2009057'
loop_
_audit_author_name
_audit_author_address
'Yang Ye'
;TianJin University
China
;
_audit_update_record             
;
2020-06-10 deposited with the CCDC.	2020-10-27 downloaded from the CCDC.
;
_audit_creation_date             2020-06-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
"4-aminoazobenzene; 1-(1-naphthyl)-2-(4'-pyridyl)ethylene"
_chemical_formula_moiety         '0.5(C12 H9 N3), 0.5(C12 H11 N3), C17 H13 N'
_chemical_formula_sum            'C29 H24 N4'
_chemical_formula_weight         428.52
_chemical_melting_point          348.73
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   25.715(5)
_cell_length_b                   5.9027(12)
_cell_length_c                   31.344(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.76(3)
_cell_angle_gamma                90
_cell_volume                     4531.0(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5665
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9865
_cell_measurement_theta_min      1.8009
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.7842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            38825
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.020
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         1.960
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5039
_reflns_number_total             7955
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0046(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     646
_refine_ls_number_reflns         7955
_refine_ls_number_restraints     108
_refine_ls_R_factor_all          0.1220
_refine_ls_R_factor_gt           0.0776
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1213P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1948
_refine_ls_wR_factor_ref         0.2262
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Restrained distances
 N1-H1A = N1-H1B = N4-H4A = N4-H4B
 0.9 with sigma of 0.01
 H1A-H1B = H4A-H4B
 1.5 with sigma of 0.01
 N2-N3 = N5-N6 = N5'-N6'
 1.32 with sigma of 0.01
3. Rigid bond restraints
 C7, C12
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C4, N2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C7, N3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
N5 \\sim N6 \\sim N5' \\sim N6': within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
N2 \\sim N3 \\sim N2A \\sim N3A: within 1.7A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N2) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(N2A) \\sim Ueq, Uanis(N3A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(N5')=Sof(N6')=1-FVAR(1)
 Sof(N5)=Sof(N6)=FVAR(1)
 Sof(N2A)=Sof(N3A)=1-FVAR(2)
 Sof(N2)=Sof(N3)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24),
  C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C33(H33),
 C34(H34), C35(H35), C37(H37), C38(H38), C39(H39), C40(H40), C42(H42), C43(H43),
  C45(H45), C46(H46), C47(H47), C48(H48), C50(H50), C51(H51), C52(H52),
 C54(H54), C55(H55), C56(H56), C57(H57)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 -0.07912(11) 0.1638(5) 0.91871(9) 0.0530(7) Uani 1 1 d D . . . .
H1A H -0.0979(12) 0.033(3) 0.9147(10) 0.064 Uiso 1 1 d DR . . . .
H1B H -0.0826(13) 0.248(4) 0.9415(8) 0.064 Uiso 1 1 d DR . . . .
C1 C -0.06173(11) 0.2622(5) 0.88607(10) 0.0407(7) Uani 1 1 d . . . . .
C2 C -0.03659(12) 0.4765(5) 0.89280(10) 0.0470(8) Uani 1 1 d . . . . .
H2 H -0.033577 0.556666 0.919728 0.056 Uiso 1 1 calc R . . . .
C3 C -0.01611(12) 0.5730(6) 0.86084(12) 0.0531(9) Uani 1 1 d . . . . .
C4 C -0.02104(13) 0.4513(6) 0.82085(11) 0.0551(9) Uani 1 1 d . U . . .
C5 C -0.04621(13) 0.2424(6) 0.81394(11) 0.0562(9) Uani 1 1 d . . . . .
H5 H -0.049492 0.162287 0.786958 0.067 Uiso 1 1 calc R . . . .
C6 C -0.06653(13) 0.1491(6) 0.84558(11) 0.0519(8) Uani 1 1 d . . . . .
H6 H -0.084143 0.005837 0.840070 0.062 Uiso 1 1 calc R . . . .
C7 C 0.04166(12) 0.7721(6) 0.75429(11) 0.0529(8) Uani 1 1 d . U . . .
C8 C 0.06627(13) 0.9767(6) 0.76252(11) 0.0554(9) Uani 1 1 d . . . . .
H8 H 0.064993 1.061890 0.787899 0.066 Uiso 1 1 calc R . . . .
C9 C 0.09306(14) 1.0616(6) 0.73436(11) 0.0549(9) Uani 1 1 d . . . . .
H9 H 0.110484 1.204984 0.740629 0.066 Uiso 1 1 calc R . . . .
C10 C 0.09520(13) 0.9427(6) 0.69708(10) 0.0503(8) Uani 1 1 d . . . . .
H10 H 0.114469 1.001514 0.678045 0.060 Uiso 1 1 calc R . . . .
C11 C 0.06875(13) 0.7362(6) 0.68794(11) 0.0557(9) Uani 1 1 d . . . . .
H11 H 0.069258 0.654066 0.662000 0.067 Uiso 1 1 calc R . . . .
C12 C 0.04114(13) 0.6460(6) 0.71646(13) 0.0592(9) Uani 1 1 d . U . . .
N2 N -0.00177(15) 0.5134(7) 0.78468(16) 0.0404(10) Uani 0.763(9) 1 d D U P A 3
N3 N 0.01922(18) 0.7132(8) 0.79040(16) 0.0427(10) Uani 0.763(9) 1 d D U P A 3
N2A N 0.0100(7) 0.653(3) 0.8018(6) 0.047(3) Uani 0.237(9) 1 d . U P A 4
N3A N 0.0099(6) 0.572(2) 0.7674(5) 0.048(3) Uani 0.237(9) 1 d . U P A 4
N4 N 0.66775(11) 0.1328(5) 0.68551(9) 0.0504(7) Uani 1 1 d D . . . .
H4A H 0.6477(11) 0.009(3) 0.6753(9) 0.060 Uiso 1 1 d DR . . . .
H4B H 0.6630(12) 0.189(4) 0.7108(7) 0.060 Uiso 1 1 d DR . . . .
C13 C 0.68291(11) 0.2673(5) 0.65598(10) 0.0431(7) Uani 1 1 d . . . . .
C14 C 0.70720(13) 0.4797(5) 0.66924(12) 0.0519(8) Uani 1 1 d . . . . .
H14 H 0.711096 0.534770 0.698529 0.062 Uiso 1 1 calc R . . . .
C15 C 0.72542(13) 0.6089(6) 0.63992(15) 0.0646(11) Uani 1 1 d . . . . .
H15 H 0.742187 0.751183 0.649491 0.078 Uiso 1 1 calc R . . . .
C16 C 0.71963(15) 0.5338(7) 0.59640(14) 0.0658(11) Uani 1 1 d . . . . .
C17 C 0.69401(15) 0.3280(7) 0.58317(12) 0.0611(10) Uani 1 1 d . . . . .
H17 H 0.688751 0.276670 0.553422 0.073 Uiso 1 1 calc R . . . .
C18 C 0.67609(13) 0.1965(6) 0.61171(11) 0.0495(8) Uani 1 1 d . . . . .
H18 H 0.658829 0.055700 0.601576 0.059 Uiso 1 1 calc R . . . .
C19 C 0.77189(14) 0.8729(7) 0.52663(14) 0.0644(11) Uani 1 1 d . . . . .
C20 C 0.76743(13) 0.7937(6) 0.48447(14) 0.0610(10) Uani 1 1 d . . . . .
H20 H 0.751726 0.649412 0.475114 0.073 Uiso 1 1 calc R . . . .
C21 C 0.78594(13) 0.9257(6) 0.45588(11) 0.0556(9) Uani 1 1 d . . . . .
H21 H 0.782593 0.872406 0.426556 0.067 Uiso 1 1 calc R . . . .
C22 C 0.80919(13) 1.1333(6) 0.46932(12) 0.0546(9) Uani 1 1 d . . . . .
H22 H 0.822618 1.222155 0.449684 0.066 Uiso 1 1 calc R . . . .
C23 C 0.81285(14) 1.2114(6) 0.51130(13) 0.0615(10) Uani 1 1 d . . . . .
H23 H 0.828237 1.356282 0.520561 0.074 Uiso 1 1 calc R . . . .
C24 C 0.79462(15) 1.0827(8) 0.53981(12) 0.0689(11) Uani 1 1 d . . . . .
H24 H 0.797568 1.137820 0.568936 0.083 Uiso 1 1 calc R . . . .
N5 N 0.7305(2) 0.6221(10) 0.5562(3) 0.0439(17) Uani 0.548(12) 1 d D U P B 1
N6 N 0.7596(2) 0.7983(10) 0.5677(3) 0.0448(16) Uani 0.548(12) 1 d D U P B 1
N5' N 0.7484(3) 0.7211(17) 0.5822(2) 0.0442(19) Uani 0.452(12) 1 d D U P B 2
N6' N 0.7453(4) 0.6682(16) 0.5420(2) 0.0440(19) Uani 0.452(12) 1 d D U P B 2
N7 N 0.08251(10) 0.5033(5) 1.00551(8) 0.0480(7) Uani 1 1 d . . . . .
C25 C 0.05563(12) 0.3068(6) 0.99390(11) 0.0495(8) Uani 1 1 d . . . . .
H25 H 0.027587 0.271195 1.006726 0.059 Uiso 1 1 calc R . . . .
C26 C 0.06630(12) 0.1546(6) 0.96461(11) 0.0495(8) Uani 1 1 d . . . . .
H26 H 0.044747 0.021438 0.956820 0.059 Uiso 1 1 calc R . . . .
C27 C 0.10831(11) 0.1929(5) 0.94619(9) 0.0425(7) Uani 1 1 d . . . . .
C28 C 0.13733(12) 0.3948(5) 0.95861(10) 0.0441(8) Uani 1 1 d . . . . .
H28 H 0.166469 0.431713 0.947135 0.053 Uiso 1 1 calc R . . . .
C29 C 0.12311(12) 0.5401(6) 0.98782(10) 0.0479(8) Uani 1 1 d . . . . .
H29 H 0.143581 0.675867 0.995943 0.057 Uiso 1 1 calc R . . . .
C30 C 0.11910(12) 0.0308(6) 0.91448(10) 0.0487(8) Uani 1 1 d . . . . .
H30 H 0.092415 -0.083889 0.903592 0.058 Uiso 1 1 calc R . . . .
C31 C 0.16157(11) 0.0260(5) 0.89939(9) 0.0397(7) Uani 1 1 d . . . . .
H31 H 0.187870 0.142686 0.909642 0.048 Uiso 1 1 calc R . . . .
C32 C 0.17265(11) -0.1398(5) 0.86848(9) 0.0401(7) Uani 1 1 d . . . . .
C33 C 0.14097(12) -0.3308(6) 0.85679(10) 0.0466(8) Uani 1 1 d . . . . .
H33 H 0.112204 -0.355024 0.869402 0.056 Uiso 1 1 calc R . . . .
C34 C 0.14998(13) -0.4918(6) 0.82659(10) 0.0492(8) Uani 1 1 d . . . . .
H34 H 0.127221 -0.621758 0.819091 0.059 Uiso 1 1 calc R . . . .
C35 C 0.19092(13) -0.4627(6) 0.80813(10) 0.0492(8) Uani 1 1 d . . . . .
H35 H 0.196238 -0.571665 0.787541 0.059 Uiso 1 1 calc R . . . .
C36 C 0.22564(12) -0.2724(6) 0.81923(9) 0.0438(7) Uani 1 1 d . . . . .
C37 C 0.26953(13) -0.2429(6) 0.80129(10) 0.0521(8) Uani 1 1 d . . . . .
H37 H 0.275411 -0.352264 0.781003 0.062 Uiso 1 1 calc R . . . .
C38 C 0.30350(13) -0.0604(6) 0.81264(11) 0.0560(9) Uani 1 1 d . . . . .
H38 H 0.332584 -0.042807 0.800139 0.067 Uiso 1 1 calc R . . . .
C39 C 0.29543(13) 0.1012(6) 0.84277(11) 0.0527(8) Uani 1 1 d . . . . .
H39 H 0.319470 0.227034 0.850882 0.063 Uiso 1 1 calc R . . . .
C40 C 0.25331(12) 0.0798(5) 0.86063(10) 0.0458(8) Uani 1 1 d . . . . .
H40 H 0.248201 0.192628 0.880591 0.055 Uiso 1 1 calc R . . . .
C41 C 0.21708(11) -0.1079(5) 0.84988(9) 0.0398(7) Uani 1 1 d . . . . .
N8 N 0.34400(11) 0.6459(5) 0.23064(9) 0.0567(7) Uani 1 1 d . . . . .
C42 C 0.31888(14) 0.4511(7) 0.21608(12) 0.0647(10) Uani 1 1 d . . . . .
H42 H 0.288342 0.411450 0.225573 0.078 Uiso 1 1 calc R . . . .
C43 C 0.33409(13) 0.3041(7) 0.18837(12) 0.0600(10) Uani 1 1 d . . . . .
H43 H 0.314033 0.168182 0.179115 0.072 Uiso 1 1 calc R . . . .
C44 C 0.37852(12) 0.3518(6) 0.17369(10) 0.0462(8) Uani 1 1 d . . . . .
C45 C 0.40463(13) 0.5546(6) 0.18789(10) 0.0482(8) Uani 1 1 d . . . . .
H45 H 0.434853 0.598642 0.178365 0.058 Uiso 1 1 calc R . . . .
C46 C 0.38679(13) 0.6937(6) 0.21599(10) 0.0520(8) Uani 1 1 d . . . . .
H46 H 0.405881 0.831503 0.225547 0.062 Uiso 1 1 calc R . . . .
C47 C 0.39402(13) 0.1883(6) 0.14465(10) 0.0497(8) Uani 1 1 d . . . . .
H47 H 0.372475 0.054653 0.137766 0.060 Uiso 1 1 calc R . . . .
C48 C 0.43402(12) 0.2034(5) 0.12694(10) 0.0458(8) Uani 1 1 d . . . . .
H48 H 0.455910 0.336123 0.133706 0.055 Uiso 1 1 calc R . . . .
C49 C 0.44838(12) 0.0360(5) 0.09772(9) 0.0420(7) Uani 1 1 d . . . . .
C50 C 0.41416(13) -0.1470(6) 0.08146(10) 0.0489(8) Uani 1 1 d . . . . .
H50 H 0.381007 -0.159021 0.088742 0.059 Uiso 1 1 calc R . . . .
C51 C 0.42692(14) -0.3137(6) 0.05477(11) 0.0551(9) Uani 1 1 d . . . . .
H51 H 0.402645 -0.436988 0.044224 0.066 Uiso 1 1 calc R . . . .
C52 C 0.47407(13) -0.3001(6) 0.04383(11) 0.0554(9) Uani 1 1 d . . . . .
H52 H 0.482524 -0.415405 0.025861 0.066 Uiso 1 1 calc R . . . .
C53 C 0.51062(12) -0.1185(5) 0.05858(10) 0.0451(8) Uani 1 1 d . . . . .
C54 C 0.55972(13) -0.1018(6) 0.04685(11) 0.0537(9) Uani 1 1 d . . . . .
H54 H 0.568316 -0.216631 0.028849 0.064 Uiso 1 1 calc R . . . .
C55 C 0.59455(13) 0.0748(6) 0.06088(11) 0.0550(9) Uani 1 1 d . . . . .
H55 H 0.627182 0.083139 0.052736 0.066 Uiso 1 1 calc R . . . .
C56 C 0.58214(13) 0.2447(6) 0.08741(11) 0.0545(9) Uani 1 1 d . . . . .
H56 H 0.606552 0.368261 0.097144 0.065 Uiso 1 1 calc R . . . .
C57 C 0.53556(12) 0.2354(6) 0.09946(10) 0.0493(8) Uani 1 1 d . . . . .
H57 H 0.528113 0.352500 0.117547 0.059 Uiso 1 1 calc R . . . .
C58 C 0.49786(12) 0.0536(5) 0.08548(9) 0.0405(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 H1A 0.896(10) . ?
N1 H1B 0.897(10) . ?
N1 C1 1.365(4) . ?
C1 C2 1.407(4) . ?
C1 C6 1.406(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(4) . ?
C3 C4 1.416(5) . ?
C4 C5 1.379(5) . ?
C4 N2 1.417(6) . ?
C4 N2A 1.64(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.369(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.352(5) . ?
C7 C12 1.397(5) . ?
C7 N3 1.461(6) . ?
C7 N3A 1.562(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.369(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.405(5) . ?
N2 N3 1.286(7) . ?
N2A N3A 1.18(3) . ?
N4 H4A 0.897(10) . ?
N4 H4B 0.902(10) . ?
N4 C13 1.364(4) . ?
C13 C14 1.406(4) . ?
C13 C18 1.408(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.398(5) . ?
C16 C17 1.384(5) . ?
C16 N5 1.467(10) . ?
C16 N5' 1.474(12) . ?
C17 H17 0.9500 . ?
C17 C18 1.366(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.373(5) . ?
C19 C24 1.378(6) . ?
C19 N6 1.484(10) . ?
C19 N6' 1.536(12) . ?
C20 H20 0.9500 . ?
C20 C21 1.377(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.372(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.370(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.360(5) . ?
C24 H24 0.9500 . ?
N5 N6 1.267(7) . ?
N5' N6' 1.276(8) . ?
N7 C25 1.342(4) . ?
N7 C29 1.341(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.371(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.390(4) . ?
C27 C28 1.397(4) . ?
C27 C30 1.466(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.383(4) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C30 C31 1.316(4) . ?
C31 H31 0.9500 . ?
C31 C32 1.465(4) . ?
C32 C33 1.373(4) . ?
C32 C41 1.445(4) . ?
C33 H33 0.9500 . ?
C33 C34 1.409(4) . ?
C34 H34 0.9500 . ?
C34 C35 1.358(4) . ?
C35 H35 0.9500 . ?
C35 C36 1.411(4) . ?
C36 C37 1.417(4) . ?
C36 C41 1.430(4) . ?
C37 H37 0.9500 . ?
C37 C38 1.364(5) . ?
C38 H38 0.9500 . ?
C38 C39 1.401(4) . ?
C39 H39 0.9500 . ?
C39 C40 1.368(4) . ?
C40 H40 0.9500 . ?
C40 C41 1.420(4) . ?
N8 C42 1.330(4) . ?
N8 C46 1.345(4) . ?
C42 H42 0.9500 . ?
C42 C43 1.366(5) . ?
C43 H43 0.9500 . ?
C43 C44 1.385(4) . ?
C44 C45 1.378(4) . ?
C44 C47 1.463(4) . ?
C45 H45 0.9500 . ?
C45 C46 1.381(4) . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
C47 C48 1.312(4) . ?
C48 H48 0.9500 . ?
C48 C49 1.469(4) . ?
C49 C50 1.388(4) . ?
C49 C58 1.440(4) . ?
C50 H50 0.9500 . ?
C50 C51 1.394(4) . ?
C51 H51 0.9500 . ?
C51 C52 1.359(4) . ?
C52 H52 0.9500 . ?
C52 C53 1.407(4) . ?
C53 C54 1.422(4) . ?
C53 C58 1.421(4) . ?
C54 H54 0.9500 . ?
C54 C55 1.357(5) . ?
C55 H55 0.9500 . ?
C55 C56 1.400(5) . ?
C56 H56 0.9500 . ?
C56 C57 1.362(4) . ?
C57 H57 0.9500 . ?
C57 C58 1.423(4) . ?

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
H1A N1 H1B 114.1(16) . . ?
C1 N1 H1A 123.1(18) . . ?
C1 N1 H1B 119.6(19) . . ?
N1 C1 C2 120.7(3) . . ?
N1 C1 C6 121.1(3) . . ?
C6 C1 C2 118.2(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 C4 118.6(3) . . ?
C3 C4 N2 128.2(4) . . ?
C3 C4 N2A 91.8(7) . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 N2 111.6(3) . . ?
C5 C4 N2A 147.9(7) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C12 121.4(3) . . ?
C8 C7 N3 109.7(3) . . ?
C8 C7 N3A 151.4(7) . . ?
C12 C7 N3 128.9(4) . . ?
C12 C7 N3A 87.1(7) . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.1(3) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.2(3) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.7(3) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 120.9(3) . . ?
C12 C11 H11 119.5 . . ?
C7 C12 C11 117.5(3) . . ?
N3 N2 C4 111.1(5) . . ?
N2 N3 C7 111.0(5) . . ?
N3A N2A C4 100.0(17) . . ?
N2A N3A C7 94.6(15) . . ?
H4A N4 H4B 113.3(16) . . ?
C13 N4 H4A 119.0(18) . . ?
C13 N4 H4B 121.8(18) . . ?
N4 C13 C14 120.8(3) . . ?
N4 C13 C18 121.4(3) . . ?
C14 C13 C18 117.8(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.2(4) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 N5 137.2(5) . . ?
C15 C16 N5' 98.3(4) . . ?
C17 C16 C15 118.0(3) . . ?
C17 C16 N5 104.6(4) . . ?
C17 C16 N5' 143.6(4) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.8(4) . . ?
C18 C17 H17 119.1 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.7(3) . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C24 119.8(3) . . ?
C20 C19 N6 139.2(4) . . ?
C20 C19 N6' 96.8(4) . . ?
C24 C19 N6 100.9(4) . . ?
C24 C19 N6' 143.3(4) . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C21 119.3(3) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.7(3) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 120.3 . . ?
C23 C22 C21 119.4(3) . . ?
C23 C22 H22 120.3 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.5(4) . . ?
C24 C23 H23 119.8 . . ?
C19 C24 H24 119.9 . . ?
C23 C24 C19 120.3(4) . . ?
C23 C24 H24 119.9 . . ?
N6 N5 C16 107.3(9) . . ?
N5 N6 C19 105.1(9) . . ?
N6' N5' C16 103.2(11) . . ?
N5' N6' C19 102.5(10) . . ?
C29 N7 C25 115.4(3) . . ?
N7 C25 H25 118.1 . . ?
N7 C25 C26 123.8(3) . . ?
C26 C25 H25 118.1 . . ?
C25 C26 H26 119.6 . . ?
C25 C26 C27 120.8(3) . . ?
C27 C26 H26 119.6 . . ?
C26 C27 C28 116.1(3) . . ?
C26 C27 C30 120.5(3) . . ?
C28 C27 C30 123.4(3) . . ?
C27 C28 H28 120.4 . . ?
C29 C28 C27 119.1(3) . . ?
C29 C28 H28 120.4 . . ?
N7 C29 C28 124.7(3) . . ?
N7 C29 H29 117.6 . . ?
C28 C29 H29 117.6 . . ?
C27 C30 H30 116.3 . . ?
C31 C30 C27 127.4(3) . . ?
C31 C30 H30 116.3 . . ?
C30 C31 H31 116.5 . . ?
C30 C31 C32 127.0(3) . . ?
C32 C31 H31 116.5 . . ?
C33 C32 C31 120.4(3) . . ?
C33 C32 C41 118.5(3) . . ?
C41 C32 C31 121.1(3) . . ?
C32 C33 H33 119.1 . . ?
C32 C33 C34 121.8(3) . . ?
C34 C33 H33 119.1 . . ?
C33 C34 H34 119.7 . . ?
C35 C34 C33 120.6(3) . . ?
C35 C34 H34 119.7 . . ?
C34 C35 H35 119.7 . . ?
C34 C35 C36 120.7(3) . . ?
C36 C35 H35 119.7 . . ?
C35 C36 C37 121.4(3) . . ?
C35 C36 C41 119.4(3) . . ?
C37 C36 C41 119.2(3) . . ?
C36 C37 H37 119.4 . . ?
C38 C37 C36 121.2(3) . . ?
C38 C37 H37 119.4 . . ?
C37 C38 H38 120.0 . . ?
C37 C38 C39 119.9(3) . . ?
C39 C38 H38 120.0 . . ?
C38 C39 H39 119.6 . . ?
C40 C39 C38 120.7(3) . . ?
C40 C39 H39 119.6 . . ?
C39 C40 H40 119.4 . . ?
C39 C40 C41 121.3(3) . . ?
C41 C40 H40 119.4 . . ?
C36 C41 C32 119.0(3) . . ?
C40 C41 C32 123.3(3) . . ?
C40 C41 C36 117.7(3) . . ?
C42 N8 C46 115.3(3) . . ?
N8 C42 H42 117.8 . . ?
N8 C42 C43 124.3(3) . . ?
C43 C42 H42 117.8 . . ?
C42 C43 H43 119.8 . . ?
C42 C43 C44 120.5(3) . . ?
C44 C43 H43 119.8 . . ?
C43 C44 C47 118.8(3) . . ?
C45 C44 C43 116.1(3) . . ?
C45 C44 C47 125.2(3) . . ?
C44 C45 H45 120.0 . . ?
C44 C45 C46 119.9(3) . . ?
C46 C45 H45 120.0 . . ?
N8 C46 C45 123.9(3) . . ?
N8 C46 H46 118.0 . . ?
C45 C46 H46 118.0 . . ?
C44 C47 H47 116.0 . . ?
C48 C47 C44 128.0(3) . . ?
C48 C47 H47 116.0 . . ?
C47 C48 H48 116.7 . . ?
C47 C48 C49 126.6(3) . . ?
C49 C48 H48 116.7 . . ?
C50 C49 C48 120.0(3) . . ?
C50 C49 C58 118.1(3) . . ?
C58 C49 C48 121.9(3) . . ?
C49 C50 H50 119.0 . . ?
C49 C50 C51 122.0(3) . . ?
C51 C50 H50 119.0 . . ?
C50 C51 H51 120.0 . . ?
C52 C51 C50 120.1(3) . . ?
C52 C51 H51 120.0 . . ?
C51 C52 H52 119.3 . . ?
C51 C52 C53 121.3(3) . . ?
C53 C52 H52 119.3 . . ?
C52 C53 C54 121.6(3) . . ?
C52 C53 C58 119.2(3) . . ?
C58 C53 C54 119.2(3) . . ?
C53 C54 H54 119.4 . . ?
C55 C54 C53 121.3(3) . . ?
C55 C54 H54 119.4 . . ?
C54 C55 H55 120.2 . . ?
C54 C55 C56 119.7(3) . . ?
C56 C55 H55 120.2 . . ?
C55 C56 H56 119.5 . . ?
C57 C56 C55 121.0(3) . . ?
C57 C56 H56 119.5 . . ?
C56 C57 H57 119.4 . . ?
C56 C57 C58 121.3(3) . . ?
C58 C57 H57 119.4 . . ?
C53 C58 C49 119.3(3) . . ?
C53 C58 C57 117.6(3) . . ?
C57 C58 C49 123.1(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1B N7 0.897(10) 2.215(10) 3.104(4) 171(2) 3_567 yes
N4 H4B N8 0.902(10) 2.133(10) 3.031(4) 174(2) 3_666 yes
C46 H46 N2 0.95 2.69 3.474(5) 140.5 4_675 yes

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 C1 C2 C3 176.5(3) . . . . ?
N1 C1 C6 C5 -176.2(3) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C2 C1 C6 C5 1.5(5) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C2 C3 C4 N2 -177.9(3) . . . . ?
C2 C3 C4 N2A -179.5(6) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C3 C4 N2 N3 -4.6(5) . . . . ?
C3 C4 N2A N3A 178.9(11) . . . . ?
C4 C5 C6 C1 -0.8(5) . . . . ?
C4 N2 N3 C7 177.0(3) . . . . ?
C4 N2A N3A C7 -178.1(8) . . . . ?
C5 C4 N2 N3 176.8(3) . . . . ?
C5 C4 N2A N3A -1(2) . . . . ?
C6 C1 C2 C3 -1.1(5) . . . . ?
C7 C8 C9 C10 0.6(5) . . . . ?
C8 C7 C12 C11 2.1(5) . . . . ?
C8 C7 N3 N2 -176.4(3) . . . . ?
C8 C7 N3A N2A -1.5(18) . . . . ?
C8 C9 C10 C11 1.2(5) . . . . ?
C9 C10 C11 C12 -1.3(5) . . . . ?
C10 C11 C12 C7 -0.2(5) . . . . ?
C12 C7 C8 C9 -2.2(5) . . . . ?
C12 C7 N3 N2 2.0(6) . . . . ?
C12 C7 N3A N2A 176.2(11) . . . . ?
N2 C4 C5 C6 178.4(3) . . . . ?
N3 C7 C8 C9 176.3(3) . . . . ?
N3 C7 C12 C11 -176.2(4) . . . . ?
N2A C4 C5 C6 179.9(11) . . . . ?
N3A C7 C8 C9 175.1(10) . . . . ?
N3A C7 C12 C11 -176.7(5) . . . . ?
N4 C13 C14 C15 176.1(3) . . . . ?
N4 C13 C18 C17 -176.6(3) . . . . ?
C13 C14 C15 C16 0.8(5) . . . . ?
C14 C13 C18 C17 1.8(4) . . . . ?
C14 C15 C16 C17 1.3(5) . . . . ?
C14 C15 C16 N5 176.1(5) . . . . ?
C14 C15 C16 N5' -176.1(4) . . . . ?
C15 C16 C17 C18 -1.9(5) . . . . ?
C15 C16 N5 N6 12.2(8) . . . . ?
C15 C16 N5' N6' -179.9(5) . . . . ?
C16 C17 C18 C13 0.3(5) . . . . ?
C16 N5 N6 C19 177.0(4) . . . . ?
C16 N5' N6' C19 176.2(4) . . . . ?
C17 C16 N5 N6 -172.6(5) . . . . ?
C17 C16 N5' N6' 4.0(10) . . . . ?
C18 C13 C14 C15 -2.4(4) . . . . ?
C19 C20 C21 C22 0.7(5) . . . . ?
C20 C19 C24 C23 -0.3(5) . . . . ?
C20 C19 N6 N5 -11.3(8) . . . . ?
C20 C19 N6' N5' 178.4(6) . . . . ?
C20 C21 C22 C23 -1.4(5) . . . . ?
C21 C22 C23 C24 1.3(5) . . . . ?
C22 C23 C24 C19 -0.4(5) . . . . ?
C24 C19 C20 C21 0.1(5) . . . . ?
C24 C19 N6 N5 169.7(5) . . . . ?
C24 C19 N6' N5' -3.1(10) . . . . ?
N5 C16 C17 C18 -178.2(4) . . . . ?
N6 C19 C20 C21 -178.7(5) . . . . ?
N6 C19 C24 C23 179.0(4) . . . . ?
N5' C16 C17 C18 173.8(6) . . . . ?
N6' C19 C20 C21 179.1(4) . . . . ?
N6' C19 C24 C23 -178.6(6) . . . . ?
N7 C25 C26 C27 2.6(5) . . . . ?
C25 N7 C29 C28 1.5(5) . . . . ?
C25 C26 C27 C28 -1.3(5) . . . . ?
C25 C26 C27 C30 -179.3(3) . . . . ?
C26 C27 C28 C29 0.2(4) . . . . ?
C26 C27 C30 C31 -169.4(3) . . . . ?
C27 C28 C29 N7 -0.4(5) . . . . ?
C27 C30 C31 C32 178.5(3) . . . . ?
C28 C27 C30 C31 12.8(5) . . . . ?
C29 N7 C25 C26 -2.6(5) . . . . ?
C30 C27 C28 C29 178.2(3) . . . . ?
C30 C31 C32 C33 -8.9(5) . . . . ?
C30 C31 C32 C41 171.5(3) . . . . ?
C31 C32 C33 C34 179.0(3) . . . . ?
C31 C32 C41 C36 -178.9(3) . . . . ?
C31 C32 C41 C40 1.4(4) . . . . ?
C32 C33 C34 C35 0.3(5) . . . . ?
C33 C32 C41 C36 1.6(4) . . . . ?
C33 C32 C41 C40 -178.2(3) . . . . ?
C33 C34 C35 C36 0.8(5) . . . . ?
C34 C35 C36 C37 178.1(3) . . . . ?
C34 C35 C36 C41 -0.6(4) . . . . ?
C35 C36 C37 C38 -179.0(3) . . . . ?
C35 C36 C41 C32 -0.5(4) . . . . ?
C35 C36 C41 C40 179.2(3) . . . . ?
C36 C37 C38 C39 0.4(5) . . . . ?
C37 C36 C41 C32 -179.3(3) . . . . ?
C37 C36 C41 C40 0.4(4) . . . . ?
C37 C38 C39 C40 -0.8(5) . . . . ?
C38 C39 C40 C41 1.1(5) . . . . ?
C39 C40 C41 C32 178.9(3) . . . . ?
C39 C40 C41 C36 -0.9(4) . . . . ?
C41 C32 C33 C34 -1.5(4) . . . . ?
C41 C36 C37 C38 -0.2(4) . . . . ?
N8 C42 C43 C44 0.5(6) . . . . ?
C42 N8 C46 C45 -0.1(5) . . . . ?
C42 C43 C44 C45 -1.4(5) . . . . ?
C42 C43 C44 C47 179.0(3) . . . . ?
C43 C44 C45 C46 1.5(5) . . . . ?
C43 C44 C47 C48 179.1(3) . . . . ?
C44 C45 C46 N8 -0.8(5) . . . . ?
C44 C47 C48 C49 -179.8(3) . . . . ?
C45 C44 C47 C48 -0.5(6) . . . . ?
C46 N8 C42 C43 0.3(5) . . . . ?
C47 C44 C45 C46 -178.9(3) . . . . ?
C47 C48 C49 C50 8.6(5) . . . . ?
C47 C48 C49 C58 -170.7(3) . . . . ?
C48 C49 C50 C51 -178.0(3) . . . . ?
C48 C49 C58 C53 177.5(3) . . . . ?
C48 C49 C58 C57 -1.8(4) . . . . ?
C49 C50 C51 C52 -0.1(5) . . . . ?
C50 C49 C58 C53 -1.8(4) . . . . ?
C50 C49 C58 C57 178.9(3) . . . . ?
C50 C51 C52 C53 -0.6(5) . . . . ?
C51 C52 C53 C54 -179.3(3) . . . . ?
C51 C52 C53 C58 0.1(5) . . . . ?
C52 C53 C54 C55 179.4(3) . . . . ?
C52 C53 C58 C49 1.2(4) . . . . ?
C52 C53 C58 C57 -179.5(3) . . . . ?
C53 C54 C55 C56 0.0(5) . . . . ?
C54 C53 C58 C49 -179.5(3) . . . . ?
C54 C53 C58 C57 -0.1(4) . . . . ?
C54 C55 C56 C57 0.1(5) . . . . ?
C55 C56 C57 C58 -0.2(5) . . . . ?
C56 C57 C58 C49 179.5(3) . . . . ?
C56 C57 C58 C53 0.2(4) . . . . ?
C58 C49 C50 C51 1.3(5) . . . . ?
C58 C53 C54 C55 0.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate/n-heptane'
_chemical_properties_physical    Light-sensitive
_exptl_crystal_preparation       photochromic
