# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_A25_BE75_190
_database_code_depnum_ccdc_archive 'CCDC 1995475'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT077_A25_BE75_190        
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)ethylene molecules. 
;
_vrf_PLAT155_A25_BE75_190        
;
PROBLEM: The Triclinic Unitcell is NOT Reduced ..........     Please Do !  
RESPONSE: The unit cell was not reduce to keep it consistent with the values 
          at other temperatures.
;
_vrf_PLAT911_A25_BE75_190        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          8 Report
RESPONSE: ...
;
# end Validation Reply Form


_audit_creation_date             2020-03-10T15:53:38-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C17.60 H15.60 N2.40 O2'
_chemical_formula_weight         292.72

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0377(3)
_cell_length_b                   9.8551(4)
_cell_length_c                   10.8773(3)
_cell_angle_alpha                92.913(4)
_cell_angle_beta                 107.077(3)
_cell_angle_gamma                114.297(3)
_cell_volume                     735.96(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    16621
_cell_measurement_theta_min      4.303
_cell_measurement_theta_max      76.606

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.085
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             308
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -6 0.0337
5 2 3 0.1012
0 0 7 0.0473
-2 0 6 0.0536
-5 -2 -3 0.1148
0 -1 -7 0.0394
0 -6 -1 0.0564
-5 -5 -1 0.093
1 6 1 0.0529
4 5 1 0.0716
-4 2 0 0.1051
1 -4 3 0.0582
-3 3 -3 0.0956
0 -3 5 0.0488
-3 -4 3 0.0674
0 3 6 0.0455
-1 -4 -6 0.0412
-4 -4 -6 0.0836
-1 -6 -4 0.0452
3 6 4 0.0661
3 6 0 0.0565
0 6 4 0.0506


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.522
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.857
_shelx_estimated_absorpt_T_max   0.942

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      190(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0024766
_diffrn_orient_matrix_ub_12      0.0471022
_diffrn_orient_matrix_ub_13      -0.1483886
_diffrn_orient_matrix_ub_21      -0.0734663
_diffrn_orient_matrix_ub_22      0.1684309
_diffrn_orient_matrix_ub_23      0.0099062
_diffrn_orient_matrix_ub_31      0.2010026
_diffrn_orient_matrix_ub_32      -0.004164
_diffrn_orient_matrix_ub_33      -0.0268651
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_number            27457
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.337
_diffrn_reflns_theta_max         77.461
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.965
_reflns_Friedel_coverage         0
_reflns_number_total             3022
_reflns_number_gt                2782
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0585P)²+0.0912P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0038(8)
_refine_ls_number_reflns         3022
_refine_ls_number_parameters     223
_refine_ls_number_restraints     224
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.1023
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)ethylene and the pedal motion about the azo group, the atom 
 sites N2 and N3, were split into parts A and B. These sites were allowed to 
 free refine their site occupancies to a total value of 1. To help maintain 
 reasonable ADP and bond lengths, SIMU, RIGU, and DFIX restraints and 
 constraints were applied. At this temperature the ratio of 4,4'-azopyridine 
 to bis(4-pyridyl)ethylene was 0.20 to 0.80, respectively.  
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16530(11) 0.15816(8) 0.30664(7) 0.0395(2) Uani 1 1 d . . . . .
H1 H 0.198583 0.185663 0.388031 0.059 Uiso 1 1 calc R U . . .
O2 O 0.82471(11) 0.22853(9) 0.43258(7) 0.0450(2) Uani 1 1 d . . . . .
H2A H 0.829114 0.266529 0.505052 0.068 Uiso 1 1 calc R U . . .
N1 N 0.26117(14) 0.24736(11) 0.57116(9) 0.0409(2) Uani 1 1 d . . . . .
N2A N 0.233(4) 0.379(2) 0.939(2) 0.036(3) Uani 0.198(3) 1 d D U P A 1
N3A N 0.260(4) 0.504(2) 0.990(2) 0.039(3) Uani 0.198(3) 1 d D U P A 1
C17 C 0.2141(11) 0.3785(6) 0.9348(5) 0.0334(8) Uani 0.802(3) 1 d D U P A 2
H17 H 0.154412 0.299399 0.97676 0.04 Uiso 0.802(3) 1 calc DR U P A 2
C18 C 0.2683(10) 0.5210(6) 0.9880(6) 0.0318(6) Uani 0.802(3) 1 d D U P A 2
H18 H 0.330993 0.600767 0.947776 0.038 Uiso 0.802(3) 1 calc R U P A 2
N4 N 0.17459(13) 0.65110(10) 1.33258(8) 0.0381(2) Uani 1 1 d . . . . .
C1 C 0.31655(15) 0.15441(10) 0.27779(9) 0.0330(2) Uani 1 1 d . . . . .
C2 C 0.49477(15) 0.19228(10) 0.37451(9) 0.0330(2) Uani 1 1 d . . . . .
H2 H 0.512146 0.220417 0.46389 0.04 Uiso 1 1 calc R U . . .
C3 C 0.64777(15) 0.18925(11) 0.34126(10) 0.0351(2) Uani 1 1 d . . . . .
C4 C 0.62127(17) 0.14519(12) 0.20999(10) 0.0398(3) Uani 1 1 d . . . . .
H4 H 0.724212 0.141294 0.186326 0.048 Uiso 1 1 calc R U . . .
C5 C 0.44260(18) 0.10731(12) 0.11504(10) 0.0409(3) Uani 1 1 d . . . . .
H5 H 0.424534 0.078072 0.025713 0.049 Uiso 1 1 calc R U . . .
C6 C 0.28966(17) 0.11089(11) 0.14670(10) 0.0387(2) Uani 1 1 d . . . . .
H6 H 0.168043 0.084077 0.080079 0.046 Uiso 1 1 calc R U . . .
C7 C 0.32282(16) 0.39392(13) 0.62065(11) 0.0408(3) Uani 1 1 d . . . . .
H7 H 0.372435 0.467016 0.57079 0.049 Uiso 1 1 calc R U . . .
C8 C 0.31858(16) 0.44491(12) 0.73934(10) 0.0383(2) Uani 1 1 d . . . . .
H8 H 0.366109 0.550377 0.770518 0.046 Uiso 1 1 calc R U . . .
C9 C 0.24324(14) 0.33907(11) 0.81322(9) 0.0331(2) Uani 1 1 d D . . . .
C10 C 0.18336(16) 0.18708(12) 0.76358(10) 0.0383(2) Uani 1 1 d . . . . .
H10 H 0.13466 0.111466 0.811703 0.046 Uiso 1 1 calc R U . . .
C11 C 0.19507(16) 0.14676(12) 0.64411(11) 0.0408(3) Uani 1 1 d . . . . .
H11 H 0.154223 0.042553 0.612173 0.049 Uiso 1 1 calc R U . . .
C12 C 0.23361(14) 0.55787(11) 1.10749(9) 0.0325(2) Uani 1 1 d D . . . .
C13 C 0.28742(16) 0.70943(12) 1.15262(10) 0.0382(2) Uani 1 1 d . . . . .
H13 H 0.345426 0.784629 1.106949 0.046 Uiso 1 1 calc R U . . .
C14 C 0.25640(16) 0.75049(12) 1.26395(11) 0.0408(3) Uani 1 1 d . . . . .
H14 H 0.295293 0.854941 1.293305 0.049 Uiso 1 1 calc R U . . .
C15 C 0.12149(15) 0.50441(12) 1.28916(10) 0.0370(2) Uani 1 1 d . . . . .
H15 H 0.062437 0.431855 1.33644 0.044 Uiso 1 1 calc R U . . .
C16 C 0.14832(15) 0.45346(12) 1.17918(10) 0.0362(2) Uani 1 1 d . . . . .
H16 H 0.109129 0.348411 1.152563 0.043 Uiso 1 1 calc DR U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3557(13) . ?
O1 H1 0.84 . ?
O2 C3 1.3555(13) . ?
O2 H2A 0.84 . ?
N1 C11 1.3374(15) . ?
N1 C7 1.3405(14) . ?
N2A N3A 1.228(10) . ?
N2A C9 1.444(16) . ?
N3A C12 1.466(16) . ?
C17 C18 1.327(4) . ?
C17 C9 1.470(5) . ?
C17 H17 0.95 . ?
C18 C12 1.465(4) . ?
C18 H18 0.95 . ?
N4 C14 1.3347(15) . ?
N4 C15 1.3415(14) . ?
C1 C2 1.3903(14) . ?
C1 C6 1.3944(14) . ?
C2 C3 1.3908(15) . ?
C2 H2 0.95 . ?
C3 C4 1.3982(14) . ?
C4 C5 1.3845(17) . ?
C4 H4 0.95 . ?
C5 C6 1.3835(17) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.3764(15) . ?
C7 H7 0.95 . ?
C8 C9 1.3971(15) . ?
C8 H8 0.95 . ?
C9 C10 1.3924(14) . ?
C10 C11 1.3804(15) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
C12 C13 1.3885(15) . ?
C12 C16 1.3971(14) . ?
C13 C14 1.3795(15) . ?
C13 H13 0.95 . ?
C14 H14 0.95 . ?
C15 C16 1.3817(14) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 116.96(9) . . ?
N3A N2A C9 126.4(19) . . ?
N2A N3A C12 133.0(19) . . ?
C18 C17 C9 122.2(5) . . ?
C18 C17 H17 118.9 . . ?
C9 C17 H17 118.9 . . ?
C17 C18 C12 121.4(5) . . ?
C17 C18 H18 119.3 . . ?
C12 C18 H18 119.3 . . ?
C14 N4 C15 117.06(9) . . ?
O1 C1 C2 121.93(9) . . ?
O1 C1 C6 118.14(9) . . ?
C2 C1 C6 119.93(10) . . ?
C1 C2 C3 120.42(9) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.06(9) . . ?
O2 C3 C4 118.10(9) . . ?
C2 C3 C4 119.84(10) . . ?
C5 C4 C3 118.94(10) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C6 C5 C4 121.80(9) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 119.06(10) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.97(10) . . ?
N1 C7 H7 118 . . ?
C8 C7 H7 118 . . ?
C7 C8 C9 118.92(10) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 117.23(9) . . ?
C10 C9 N2A 118.7(8) . . ?
C8 C9 N2A 124.0(8) . . ?
C10 C9 C17 118.9(2) . . ?
C8 C9 C17 123.7(2) . . ?
C11 C10 C9 119.70(10) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N1 C11 C10 123.16(10) . . ?
N1 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
C13 C12 C16 116.97(9) . . ?
C13 C12 C18 117.3(2) . . ?
C16 C12 C18 125.7(2) . . ?
C13 C12 N3A 123.5(8) . . ?
C16 C12 N3A 119.5(8) . . ?
C14 C13 C12 119.81(10) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
N4 C14 C13 123.42(10) . . ?
N4 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
N4 C15 C16 123.35(10) . . ?
N4 C15 H15 118.3 . . ?
C16 C15 H15 118.3 . . ?
C15 C16 C12 119.39(10) . . ?
C15 C16 H16 120.3 . . ?
C12 C16 H16 120.3 . . ?

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
O1 H1 N1 0.84 1.9 2.7438(11) 177.1 . yes
O2 H2A N4 0.84 1.92 2.7587(11) 177.2 2_667 yes

####################################################################### 
# 
# 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_A25_BE75_210
_database_code_depnum_ccdc_archive 'CCDC 1995476'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT077_A25_BE75_210        
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)ethylene molecules.
;
_vrf_PLAT155_A25_BE75_210        
;
PROBLEM: The Triclinic Unitcell is NOT Reduced ..........     Please Do !  
RESPONSE: The unit cell was not reduce to keep it consistent with the values 
          at other temperatures.
;
_vrf_PLAT911_A25_BE75_210        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          4 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2020-03-10T15:55:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C17.57 H15.57 N2.43 O2'
_chemical_formula_weight         292.75

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.05644(11)
_cell_length_b                   9.86768(17)
_cell_length_c                   10.88249(16)
_cell_angle_alpha                92.9895(18)
_cell_angle_beta                 107.0934(13)
_cell_angle_gamma                114.3019(13)
_cell_volume                     738.62(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    16051
_cell_measurement_theta_min      4.306
_cell_measurement_theta_max      76.965

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.085
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             308
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -6 0.0337
3 6 0 0.0565
-2 0 6 0.0536
1 6 1 0.0529
0 -6 -1 0.0564
5 2 3 0.1012
-5 -5 -1 0.093
0 6 4 0.0506
0 0 7 0.0473
-4 2 0 0.1051
1 -4 3 0.0582
-3 -4 3 0.0674
-1 -1 -7 0.0394
0 -3 5 0.0488
0 3 6 0.0455
-1 -4 -6 0.0412
-4 -4 -5 0.0836
-1 -6 -4 0.0452
3 6 4 0.0661
-3 3 -3 0.0956
-5 -2 -3 0.1148
4 5 1 0.0716


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.522
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.857
_shelx_estimated_absorpt_T_max   0.942

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      210(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0007709
_diffrn_orient_matrix_ub_12      0.0471249
_diffrn_orient_matrix_ub_13      -0.148165
_diffrn_orient_matrix_ub_21      -0.073349
_diffrn_orient_matrix_ub_22      0.168272
_diffrn_orient_matrix_ub_23      0.0096655
_diffrn_orient_matrix_ub_31      0.200578
_diffrn_orient_matrix_ub_32      -0.0037922
_diffrn_orient_matrix_ub_33      -0.0281225
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_number            27429
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.337
_diffrn_reflns_theta_max         77.205
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.968
_reflns_Friedel_coverage         0
_reflns_number_total             3036
_reflns_number_gt                2761
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0616P)²+0.0829P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0041(9)
_refine_ls_number_reflns         3036
_refine_ls_number_parameters     242
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.1084
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.034

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)ethylene and the pedal motion about the azo group, the atom 
 sites N2 and N3, were split into parts A and B. These sites were allowed to 
 free refine their site occupancies to a total value of 1. To help maintain 
 reasonable ADP and bond lengths, SIMU, RIGU, and DFIX restraints and 
 constraints were applied. At this temperature the ratio of 4,4'-azopyridine 
 to bis(4-pyridyl)ethylene was 0.20 to 0.78 with the amount of 
 4,4'-azopyridine in the secondary position calculated at 0.02. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16572(11) 0.15772(9) 0.30656(7) 0.0437(2) Uani 1 1 d . . . . .
H1 H 0.198664 0.185478 0.386917 0.066 Uiso 1 1 calc R U . . .
O2 O 0.82386(12) 0.22858(10) 0.43224(8) 0.0498(2) Uani 1 1 d . . . . .
H2A H 0.828147 0.265696 0.503989 0.075 Uiso 1 1 calc R U . . .
N1 N 0.26109(14) 0.24720(11) 0.57132(9) 0.0449(2) Uani 1 1 d . . . . .
N2A N 0.233(4) 0.379(2) 0.9421(19) 0.037(2) Uani 0.196(3) 1 d D U P A 1
N3A N 0.269(4) 0.507(2) 0.993(2) 0.040(3) Uani 0.196(3) 1 d D U P A 1
C17 C 0.2139(11) 0.3786(7) 0.9340(5) 0.0363(8) Uani 0.786(3) 1 d D U P A 2
H17 H 0.155999 0.300224 0.975521 0.044 Uiso 0.786(3) 1 calc DR U P A 2
C18 C 0.2656(12) 0.5199(7) 0.9871(6) 0.0348(6) Uani 0.786(3) 1 d D U P A 2
H18 H 0.324663 0.598658 0.94629 0.042 Uiso 0.786(3) 1 calc R U P A 2
N2B N 0.251(8) 0.457(7) 0.919(5) 0.038(3) Uani 0.0179(16) 1 d D U P A 3
N3B N 0.185(7) 0.408(6) 1.006(4) 0.039(3) Uani 0.0179(16) 1 d D U P A 3
N4 N 0.17513(13) 0.65115(11) 1.33254(8) 0.0417(2) Uani 1 1 d . . . . .
C1 C 0.31681(16) 0.15417(10) 0.27792(10) 0.0362(2) Uani 1 1 d . . . . .
C2 C 0.49448(15) 0.19204(11) 0.37432(9) 0.0363(2) Uani 1 1 d . . . . .
H2 H 0.511742 0.219819 0.462776 0.044 Uiso 1 1 calc R U . . .
C3 C 0.64730(16) 0.18922(11) 0.34110(10) 0.0386(2) Uani 1 1 d . . . . .
C4 C 0.62086(18) 0.14526(12) 0.20983(11) 0.0439(3) Uani 1 1 d . . . . .
H4 H 0.722508 0.141575 0.186365 0.053 Uiso 1 1 calc R U . . .
C5 C 0.44281(19) 0.10734(12) 0.11523(10) 0.0454(3) Uani 1 1 d . . . . .
H5 H 0.424917 0.078395 0.026833 0.054 Uiso 1 1 calc R U . . .
C6 C 0.28991(17) 0.11071(12) 0.14672(10) 0.0424(3) Uani 1 1 d . . . . .
H6 H 0.169813 0.084114 0.080739 0.051 Uiso 1 1 calc R U . . .
C7 C 0.32241(17) 0.39358(13) 0.62046(11) 0.0451(3) Uani 1 1 d . . . . .
H7 H 0.371057 0.465612 0.570975 0.054 Uiso 1 1 calc R U . . .
C8 C 0.31841(17) 0.44479(12) 0.73915(11) 0.0420(3) Uani 1 1 d . . . . .
H8 H 0.365423 0.549085 0.769973 0.05 Uiso 1 1 calc R U . . .
C9 C 0.24343(15) 0.33937(12) 0.81305(10) 0.0364(2) Uani 1 1 d D . . . .
C10 C 0.18345(16) 0.18756(12) 0.76343(11) 0.0423(3) Uani 1 1 d . . . . .
H10 H 0.135128 0.1129 0.810938 0.051 Uiso 1 1 calc R U . . .
C11 C 0.19528(17) 0.14719(13) 0.64417(11) 0.0450(3) Uani 1 1 d . . . . .
H11 H 0.154996 0.044138 0.612637 0.054 Uiso 1 1 calc R U . . .
C12 C 0.23360(14) 0.55764(12) 1.10759(10) 0.0358(2) Uani 1 1 d D . . . .
C13 C 0.28711(16) 0.70879(12) 1.15259(11) 0.0423(3) Uani 1 1 d . . . . .
H13 H 0.344215 0.783016 1.107368 0.051 Uiso 1 1 calc R U . . .
C14 C 0.25637(17) 0.75000(12) 1.26384(11) 0.0447(3) Uani 1 1 d . . . . .
H14 H 0.294737 0.853289 1.2928 0.054 Uiso 1 1 calc R U . . .
C15 C 0.12201(16) 0.50469(13) 1.28921(10) 0.0408(2) Uani 1 1 d . . . . .
H15 H 0.063717 0.433129 1.336001 0.049 Uiso 1 1 calc R U . . .
C16 C 0.14857(16) 0.45349(12) 1.17926(10) 0.0401(2) Uani 1 1 d . . . . .
H16 H 0.109806 0.349614 1.152936 0.048 Uiso 1 1 calc DR U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3554(13) . ?
O1 H1 0.83 . ?
O2 C3 1.3541(13) . ?
O2 H2A 0.83 . ?
N1 C11 1.3348(15) . ?
N1 C7 1.3391(15) . ?
N2A N3A 1.234(10) . ?
N2A C9 1.472(16) . ?
N3A C12 1.466(17) . ?
C17 C18 1.322(4) . ?
C17 C9 1.465(5) . ?
C17 H17 0.94 . ?
C18 C12 1.467(5) . ?
C18 H18 0.94 . ?
N2B N3B 1.242(10) . ?
N2B C9 1.56(6) . ?
N3B C12 1.63(5) . ?
N4 C14 1.3330(15) . ?
N4 C15 1.3399(14) . ?
C1 C2 1.3875(15) . ?
C1 C6 1.3953(14) . ?
C2 C3 1.3915(15) . ?
C2 H2 0.94 . ?
C3 C4 1.3981(14) . ?
C4 C5 1.3811(17) . ?
C4 H4 0.94 . ?
C5 C6 1.3845(17) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3765(15) . ?
C7 H7 0.94 . ?
C8 C9 1.3962(15) . ?
C8 H8 0.94 . ?
C9 C10 1.3912(15) . ?
C10 C11 1.3792(15) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.3859(15) . ?
C12 C16 1.3971(15) . ?
C13 C14 1.3785(16) . ?
C13 H13 0.94 . ?
C14 H14 0.94 . ?
C15 C16 1.3817(15) . ?
C15 H15 0.94 . ?
C16 H16 0.94 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 117.00(9) . . ?
N3A N2A C9 124.7(18) . . ?
N2A N3A C12 130.5(19) . . ?
C18 C17 C9 122.6(5) . . ?
C18 C17 H17 118.7 . . ?
C9 C17 H17 118.7 . . ?
C17 C18 C12 122.1(5) . . ?
C17 C18 H18 118.9 . . ?
C12 C18 H18 118.9 . . ?
N3B N2B C9 117(5) . . ?
N2B N3B C12 106(5) . . ?
C14 N4 C15 117.04(9) . . ?
O1 C1 C2 122.10(9) . . ?
O1 C1 C6 118.05(10) . . ?
C2 C1 C6 119.84(10) . . ?
C1 C2 C3 120.53(9) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O2 C3 C2 122.14(9) . . ?
O2 C3 C4 118.03(10) . . ?
C2 C3 C4 119.83(10) . . ?
C5 C4 C3 118.85(11) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.95(10) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.99(10) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.87(10) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.95(10) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 117.22(10) . . ?
C10 C9 C17 118.8(3) . . ?
C8 C9 C17 123.8(3) . . ?
C10 C9 N2A 118.2(8) . . ?
C8 C9 N2A 124.5(8) . . ?
C10 C9 N2B 147.2(18) . . ?
C8 C9 N2B 95.2(18) . . ?
C11 C10 C9 119.65(10) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
N1 C11 C10 123.25(10) . . ?
N1 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
C13 C12 C16 116.97(10) . . ?
C13 C12 N3A 122.5(9) . . ?
C16 C12 N3A 120.5(9) . . ?
C13 C12 C18 117.5(3) . . ?
C16 C12 C18 125.5(3) . . ?
C13 C12 N3B 157.7(15) . . ?
C16 C12 N3B 84.8(15) . . ?
C14 C13 C12 119.82(10) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
N4 C14 C13 123.48(10) . . ?
N4 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
N4 C15 C16 123.34(10) . . ?
N4 C15 H15 118.3 . . ?
C16 C15 H15 118.3 . . ?
C15 C16 C12 119.35(10) . . ?
C15 C16 H16 120.3 . . ?
C12 C16 H16 120.3 . . ?

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
O1 H1 N1 0.83 1.92 2.7470(12) 177 . yes
O2 H2A N4 0.83 1.93 2.7612(12) 177.3 2_667 yes

####################################################################### 
# 
# 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_A50_BE50_270
_database_code_depnum_ccdc_archive 'CCDC 1995486'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT230_A50_BE50_270        
;
PROBLEM: Hirshfeld Test Diff for    C12      --C16      .        5.7 s.u.  
RESPONSE: Due to the pedal motion of the 4,4'-azopyridine molecule.
;
# end Validation Reply Form

_audit_creation_date             2020-03-05T13:03:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C17.03 H15.03 N2.97 O2'
_chemical_formula_weight         293.29

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.06741(16)
_cell_length_b                   9.8484(2)
_cell_length_c                   10.8930(2)
_cell_angle_alpha                93.6858(16)
_cell_angle_beta                 106.6746(17)
_cell_angle_gamma                113.951(2)
_cell_volume                     741.36(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    10527
_cell_measurement_theta_min      4.3
_cell_measurement_theta_max      75.103

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.102
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             308
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -2 1 0.0681
3 3 -3 0.0873
0 6 -2 0.0863
4 1 -1 0.0905
-1 -2 -5 0.0457
0 -6 2 0.0494
2 2 -7 0.0731
-1 0 7 0.036
-2 1 -5 0.0681
0 4 -6 0.0553
3 0 4 0.092
4 -5 -3 0.1384
-3 6 2 0.1189
1 -3 -5 0.0535
0 0 -7 0.0505
-3 6 -2 0.1171


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.501
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.87
_shelx_estimated_absorpt_T_max   0.93

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      270(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.1310714
_diffrn_orient_matrix_ub_12      -0.0768257
_diffrn_orient_matrix_ub_13      0.0521445
_diffrn_orient_matrix_ub_21      0.0232978
_diffrn_orient_matrix_ub_22      0.0588304
_diffrn_orient_matrix_ub_23      0.1413733
_diffrn_orient_matrix_ub_31      -0.1782397
_diffrn_orient_matrix_ub_32      -0.1457368
_diffrn_orient_matrix_ub_33      -0.0078161
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.061
_diffrn_reflns_number            20462
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.33
_diffrn_reflns_theta_max         77.174
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.932
_reflns_Friedel_coverage         0
_reflns_number_total             2931
_reflns_number_gt                2327
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0590P)²+0.1058P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0055(9)
_refine_ls_number_reflns         2931
_refine_ls_number_parameters     242
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1087
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.032

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)ethylene and the pedal motion about the azo group, the atom 
 sites N2 and N3, were split into parts A and B. These sites were allowed to 
 free refine their site occupancies to a total value of 1. To help maintain 
 reasonable ADP and bond lengths, SIMU, RIGU, and DFIX restraints and 
 constraints were applied. At this temperature the ratio of 4,4'-azopyridine 
 to bis(4-pyridyl)ethylene was 0.49 to 0.51 with the amount of 
 4,4'-azopyridine in the secondary position calculated at 0.08. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16629(15) 0.15689(13) 0.30927(10) 0.0611(3) Uani 1 1 d . . . . .
H1 H 0.196615 0.179681 0.388969 0.092 Uiso 1 1 calc R U . . .
O2 O 0.82063(16) 0.22537(15) 0.43234(11) 0.0703(4) Uani 1 1 d . . . . .
H2A H 0.825112 0.263141 0.50325 0.105 Uiso 1 1 calc R U . . .
N1 N 0.25979(19) 0.24757(16) 0.57514(12) 0.0596(3) Uani 1 1 d . . . . .
N2A N 0.225(3) 0.3794(17) 0.9440(14) 0.0502(18) Uani 0.405(3) 1 d D U P A 1
N3A N 0.272(3) 0.5129(17) 0.9898(15) 0.051(2) Uani 0.405(3) 1 d D U P A 1
C17 C 0.209(3) 0.3775(16) 0.9348(13) 0.0498(17) Uani 0.515(3) 1 d D U P A 2
H17 H 0.152183 0.300667 0.975978 0.06 Uiso 0.515(3) 1 calc DR U P A 2
C18 C 0.260(3) 0.5193(16) 0.9828(14) 0.0473(14) Uani 0.515(3) 1 d D U P A 2
H18 H 0.312864 0.596 0.940118 0.057 Uiso 0.515(3) 1 calc R U P A 2
N2B N 0.273(3) 0.468(2) 0.9229(16) 0.052(2) Uani 0.081(2) 1 d D U P A 3
N3B N 0.194(2) 0.407(2) 1.0005(16) 0.054(2) Uani 0.081(2) 1 d D U P A 3
N4 N 0.17715(18) 0.65048(15) 1.33036(12) 0.0566(3) Uani 1 1 d . . . . .
C1 C 0.3171(2) 0.15322(15) 0.27969(13) 0.0486(3) Uani 1 1 d . . . . .
C2 C 0.4932(2) 0.18968(16) 0.37549(13) 0.0493(3) Uani 1 1 d . . . . .
H2 H 0.509614 0.216187 0.463148 0.059 Uiso 1 1 calc R U . . .
C3 C 0.6453(2) 0.18692(16) 0.34155(14) 0.0527(4) Uani 1 1 d . . . . .
C4 C 0.6201(3) 0.14465(18) 0.21087(15) 0.0597(4) Uani 1 1 d . . . . .
H4 H 0.720339 0.140749 0.187227 0.072 Uiso 1 1 calc R U . . .
C5 C 0.4445(3) 0.10867(18) 0.11702(14) 0.0622(4) Uani 1 1 d . . . . .
H5 H 0.427745 0.08124 0.029426 0.075 Uiso 1 1 calc R U . . .
C6 C 0.2923(2) 0.11210(17) 0.14911(14) 0.0581(4) Uani 1 1 d . . . . .
H6 H 0.174738 0.087154 0.084011 0.07 Uiso 1 1 calc R U . . .
C7 C 0.3221(2) 0.39476(19) 0.62429(16) 0.0614(4) Uani 1 1 d . . . . .
H7 H 0.370398 0.465348 0.575431 0.074 Uiso 1 1 calc R U . . .
C8 C 0.3185(2) 0.44702(19) 0.74334(15) 0.0590(4) Uani 1 1 d . . . . .
H8 H 0.36507 0.55044 0.77434 0.071 Uiso 1 1 calc R U . . .
C9 C 0.2442(2) 0.34279(18) 0.81608(13) 0.0511(3) Uani 1 1 d D . . . .
C10 C 0.1835(2) 0.19147(18) 0.76715(15) 0.0582(4) Uani 1 1 d . . . . .
H10 H 0.135644 0.118483 0.814247 0.07 Uiso 1 1 calc R U . . .
C11 C 0.1945(2) 0.14967(19) 0.64819(15) 0.0605(4) Uani 1 1 d . . . . .
H11 H 0.154108 0.047227 0.616983 0.073 Uiso 1 1 calc R U . . .
C12 C 0.2318(2) 0.55360(18) 1.10598(13) 0.0521(4) Uani 1 1 d D . . . .
C13 C 0.2857(2) 0.70406(19) 1.14992(16) 0.0611(4) Uani 1 1 d . . . . .
H13 H 0.341481 0.77632 1.104625 0.073 Uiso 1 1 calc R U . . .
C14 C 0.2568(2) 0.74699(19) 1.26086(16) 0.0621(4) Uani 1 1 d . . . . .
H14 H 0.295182 0.849662 1.289318 0.075 Uiso 1 1 calc R U . . .
C15 C 0.1228(2) 0.50374(19) 1.28759(15) 0.0573(4) Uani 1 1 d . . . . .
H15 H 0.065382 0.434067 1.334211 0.069 Uiso 1 1 calc R U . . .
C16 C 0.1480(2) 0.45053(18) 1.17666(15) 0.0577(4) Uani 1 1 d . . . . .
H16 H 0.109426 0.347455 1.150137 0.069 Uiso 1 1 calc DR U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3581(17) . ?
O1 H1 0.82 . ?
O2 C3 1.3553(18) . ?
O2 H2A 0.82 . ?
N1 C11 1.329(2) . ?
N1 C7 1.340(2) . ?
N2A N3A 1.234(8) . ?
N2A C9 1.483(11) . ?
N3A C12 1.465(13) . ?
C17 C18 1.308(7) . ?
C17 C9 1.449(11) . ?
C17 H17 0.93 . ?
C18 C12 1.466(11) . ?
C18 H18 0.93 . ?
N2B N3B 1.241(10) . ?
N2B C9 1.532(19) . ?
N3B C12 1.649(19) . ?
N4 C14 1.329(2) . ?
N4 C15 1.334(2) . ?
C1 C2 1.387(2) . ?
C1 C6 1.3871(19) . ?
C2 C3 1.389(2) . ?
C2 H2 0.93 . ?
C3 C4 1.389(2) . ?
C4 C5 1.376(2) . ?
C4 H4 0.93 . ?
C5 C6 1.382(2) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.377(2) . ?
C7 H7 0.93 . ?
C8 C9 1.385(2) . ?
C8 H8 0.93 . ?
C9 C10 1.379(2) . ?
C10 C11 1.372(2) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 C13 1.371(2) . ?
C12 C16 1.386(2) . ?
C13 C14 1.367(2) . ?
C13 H13 0.93 . ?
C14 H14 0.93 . ?
C15 C16 1.387(2) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 116.86(13) . . ?
N3A N2A C9 118.7(12) . . ?
N2A N3A C12 121.2(12) . . ?
C18 C17 C9 118.4(11) . . ?
C18 C17 H17 120.8 . . ?
C9 C17 H17 120.8 . . ?
C17 C18 C12 117.9(11) . . ?
C17 C18 H18 121 . . ?
C12 C18 H18 121 . . ?
N3B N2B C9 108.9(18) . . ?
N2B N3B C12 103.2(16) . . ?
C14 N4 C15 117.11(13) . . ?
O1 C1 C2 122.06(12) . . ?
O1 C1 C6 118.29(13) . . ?
C2 C1 C6 119.65(14) . . ?
C1 C2 C3 120.53(13) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O2 C3 C2 122.07(12) . . ?
O2 C3 C4 118.06(14) . . ?
C2 C3 C4 119.87(14) . . ?
C5 C4 C3 118.90(15) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.93(13) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.12(15) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N1 C7 C8 123.45(15) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 118.81(15) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C8 117.94(14) . . ?
C10 C9 C17 116.4(6) . . ?
C8 C9 C17 125.4(6) . . ?
C10 C9 N2A 116.4(6) . . ?
C8 C9 N2A 125.7(6) . . ?
C10 C9 N2B 149.9(6) . . ?
C8 C9 N2B 92.2(6) . . ?
C11 C10 C9 119.30(15) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
N1 C11 C10 123.60(15) . . ?
N1 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
C13 C12 C16 117.90(14) . . ?
C13 C12 N3A 117.8(6) . . ?
C16 C12 N3A 124.3(6) . . ?
C13 C12 C18 114.9(6) . . ?
C16 C12 C18 127.1(6) . . ?
C13 C12 N3B 154.5(5) . . ?
C16 C12 N3B 87.4(5) . . ?
C14 C13 C12 119.46(15) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
N4 C14 C13 123.78(15) . . ?
N4 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
N4 C15 C16 122.89(15) . . ?
N4 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C12 C16 C15 118.86(15) . . ?
C12 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?

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
O1 H1 N1 0.82 1.94 2.7606(16) 174.8 . yes
O2 H2A N4 0.82 1.96 2.7796(16) 177.4 2_667 yes

####################################################################### 
# 
# 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_A25_BE75_250
_database_code_depnum_ccdc_archive 'CCDC 1995478'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT077_A25_BE75_250        
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)ethylene molecules.
;
_vrf_PLAT155_A25_BE75_250        
;
PROBLEM: The Triclinic Unitcell is NOT Reduced ..........     Please Do !  
RESPONSE: The unit cell was not reduce to keep it consistent with the values 
          at other temperatures.
;
_vrf_PLAT911_A25_BE75_250        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          7 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2020-03-10T15:57:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C17.56 H15.56 N2.44 O2'
_chemical_formula_weight         292.76

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.09014(10)
_cell_length_b                   9.88806(15)
_cell_length_c                   10.89279(13)
_cell_angle_alpha                93.1584(16)
_cell_angle_beta                 107.0442(11)
_cell_angle_gamma                114.2427(11)
_cell_volume                     744.094(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    14900
_cell_measurement_theta_min      4.301
_cell_measurement_theta_max      76.673

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.085
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_F_000             308
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -6 0.0337
3 6 0 0.0565
-2 0 6 0.0536
1 6 1 0.0529
0 -6 -1 0.0564
5 2 3 0.1012
-5 -5 -1 0.093
0 6 4 0.0506
0 0 7 0.0473
-4 2 0 0.1051
1 -4 3 0.0582
-3 -4 3 0.0674
-1 -1 -7 0.0394
0 -3 5 0.0488
0 3 6 0.0455
-1 -4 -6 0.0412
-4 -4 -5 0.0836
-1 -6 -4 0.0452
3 6 4 0.0661
-3 3 -3 0.0956
-5 -2 -3 0.1148
4 5 1 0.0716


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.521
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.858
_shelx_estimated_absorpt_T_max   0.943

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      250(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0003703
_diffrn_orient_matrix_ub_12      0.0479831
_diffrn_orient_matrix_ub_13      -0.1480816
_diffrn_orient_matrix_ub_21      -0.0734179
_diffrn_orient_matrix_ub_22      0.1676634
_diffrn_orient_matrix_ub_23      0.0101147
_diffrn_orient_matrix_ub_31      0.1997235
_diffrn_orient_matrix_ub_32      -0.0038744
_diffrn_orient_matrix_ub_33      -0.0278482
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_av_unetI/netI     0.048
_diffrn_reflns_number            27432
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.334
_diffrn_reflns_theta_max         77.109
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.964
_reflns_Friedel_coverage         0
_reflns_number_total             3046
_reflns_number_gt                2675
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0608P)²+0.0704P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0043(9)
_refine_ls_number_reflns         3046
_refine_ls_number_parameters     242
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.031

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)ethylene and the pedal motion about the azo group, the atom 
 sites N2 and N3, were split into parts A and B. These sites were allowed to 
 free refine their site occupancies to a total value of 1. To help maintain 
 reasonable ADP and bond lengths, SIMU, RIGU, and DFIX restraints and 
 constraints were applied. At this temperature the ratio of 4,4'-azopyridine 
 to bis(4-pyridyl)ethylene was 0.18 to 0.78 with the amount of 
 4,4'-azopyridine in the secondary position calculated at 0.04. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16647(12) 0.15625(9) 0.30654(8) 0.0532(2) Uani 1 1 d . . . . .
H1 H 0.198952 0.183147 0.386944 0.08 Uiso 1 1 calc R U . . .
O2 O 0.82195(12) 0.22819(11) 0.43161(8) 0.0608(3) Uani 1 1 d . . . . .
H2A H 0.82567 0.264115 0.503611 0.091 Uiso 1 1 calc R U . . .
N1 N 0.26066(15) 0.24679(12) 0.57123(9) 0.0537(3) Uani 1 1 d . . . . .
N2A N 0.239(4) 0.388(2) 0.939(2) 0.042(2) Uani 0.177(3) 1 d D U P A 1
N3A N 0.269(5) 0.512(3) 0.995(2) 0.048(3) Uani 0.177(3) 1 d D U P A 1
C17 C 0.2133(9) 0.3766(7) 0.9346(5) 0.0435(9) Uani 0.780(3) 1 d D U P A 2
H17 H 0.156368 0.298139 0.976002 0.052 Uiso 0.780(3) 1 calc DR U P A 2
C18 C 0.2649(12) 0.5180(7) 0.9867(6) 0.0424(7) Uani 0.780(3) 1 d D U P A 2
H18 H 0.323431 0.596008 0.945438 0.051 Uiso 0.780(3) 1 calc R U P A 2
N2B N 0.270(3) 0.466(3) 0.919(2) 0.046(3) Uani 0.0435(17) 1 d D U P A 3
N3B N 0.199(3) 0.413(3) 1.002(2) 0.048(3) Uani 0.0435(17) 1 d D U P A 3
N4 N 0.17612(14) 0.65121(11) 1.33268(9) 0.0498(2) Uani 1 1 d . . . . .
C1 C 0.31712(16) 0.15321(11) 0.27773(10) 0.0432(2) Uani 1 1 d . . . . .
C2 C 0.49398(16) 0.19118(11) 0.37399(9) 0.0434(3) Uani 1 1 d . . . . .
H2 H 0.511141 0.218827 0.462437 0.052 Uiso 1 1 calc R U . . .
C3 C 0.64610(17) 0.18865(12) 0.34063(10) 0.0464(3) Uani 1 1 d . . . . .
C4 C 0.61989(19) 0.14508(13) 0.20950(11) 0.0528(3) Uani 1 1 d . . . . .
H4 H 0.721178 0.141689 0.185917 0.063 Uiso 1 1 calc R U . . .
C5 C 0.4428(2) 0.10712(13) 0.11525(11) 0.0544(3) Uani 1 1 d . . . . .
H5 H 0.425 0.078315 0.02686 0.065 Uiso 1 1 calc R U . . .
C6 C 0.29076(19) 0.11015(12) 0.14683(10) 0.0509(3) Uani 1 1 d . . . . .
H6 H 0.171198 0.083519 0.080885 0.061 Uiso 1 1 calc R U . . .
C7 C 0.32191(18) 0.39302(14) 0.62020(12) 0.0543(3) Uani 1 1 d . . . . .
H7 H 0.370295 0.464605 0.570675 0.065 Uiso 1 1 calc R U . . .
C8 C 0.31816(18) 0.44459(13) 0.73867(12) 0.0510(3) Uani 1 1 d . . . . .
H8 H 0.36505 0.548761 0.769377 0.061 Uiso 1 1 calc R U . . .
C9 C 0.24380(16) 0.34011(13) 0.81258(10) 0.0444(3) Uani 1 1 d D . . . .
C10 C 0.18417(18) 0.18906(13) 0.76335(11) 0.0514(3) Uani 1 1 d . . . . .
H10 H 0.136317 0.114969 0.811061 0.062 Uiso 1 1 calc R U . . .
C11 C 0.19526(18) 0.14789(14) 0.64438(12) 0.0543(3) Uani 1 1 d . . . . .
H11 H 0.154695 0.04485 0.613063 0.065 Uiso 1 1 calc R U . . .
C12 C 0.23319(15) 0.55677(13) 1.10791(10) 0.0442(3) Uani 1 1 d D . . . .
C13 C 0.28656(18) 0.70712(13) 1.15263(11) 0.0518(3) Uani 1 1 d . . . . .
H13 H 0.343236 0.780853 1.107287 0.062 Uiso 1 1 calc R U . . .
C14 C 0.25664(18) 0.74885(13) 1.26363(12) 0.0541(3) Uani 1 1 d . . . . .
H14 H 0.295191 0.852086 1.292412 0.065 Uiso 1 1 calc R U . . .
C15 C 0.12291(17) 0.50493(13) 1.28954(11) 0.0495(3) Uani 1 1 d . . . . .
H15 H 0.065066 0.43383 1.336422 0.059 Uiso 1 1 calc R U . . .
C16 C 0.14890(17) 0.45336(13) 1.17938(11) 0.0487(3) Uani 1 1 d . . . . .
H16 H 0.110122 0.349624 1.15297 0.058 Uiso 1 1 calc DR U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3558(14) . ?
O1 H1 0.83 . ?
O2 C3 1.3538(14) . ?
O2 H2A 0.83 . ?
N1 C11 1.3339(16) . ?
N1 C7 1.3389(16) . ?
N2A N3A 1.234(10) . ?
N2A C9 1.444(17) . ?
N3A C12 1.429(17) . ?
C17 C18 1.321(4) . ?
C17 C9 1.473(5) . ?
C17 H17 0.94 . ?
C18 C12 1.477(4) . ?
C18 H18 0.94 . ?
N2B N3B 1.243(10) . ?
N2B C9 1.55(2) . ?
N3B C12 1.66(3) . ?
N4 C14 1.3315(16) . ?
N4 C15 1.3392(15) . ?
C1 C2 1.3870(15) . ?
C1 C6 1.3929(14) . ?
C2 C3 1.3905(16) . ?
C2 H2 0.94 . ?
C3 C4 1.3966(15) . ?
C4 C5 1.3787(18) . ?
C4 H4 0.94 . ?
C5 C6 1.3820(18) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3745(16) . ?
C7 H7 0.94 . ?
C8 C9 1.3937(16) . ?
C8 H8 0.94 . ?
C9 C10 1.3855(16) . ?
C10 C11 1.3760(16) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.3798(16) . ?
C12 C16 1.3939(16) . ?
C13 C14 1.3745(17) . ?
C13 H13 0.94 . ?
C14 H14 0.94 . ?
C15 C16 1.3830(16) . ?
C15 H15 0.94 . ?
C16 H16 0.94 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 116.82(10) . . ?
N3A N2A C9 132(2) . . ?
N2A N3A C12 133(2) . . ?
C18 C17 C9 120.9(5) . . ?
C18 C17 H17 119.6 . . ?
C9 C17 H17 119.6 . . ?
C17 C18 C12 121.7(5) . . ?
C17 C18 H18 119.1 . . ?
C12 C18 H18 119.1 . . ?
N3B N2B C9 112(2) . . ?
N2B N3B C12 107(2) . . ?
C14 N4 C15 116.87(10) . . ?
O1 C1 C2 122.07(9) . . ?
O1 C1 C6 118.15(10) . . ?
C2 C1 C6 119.78(10) . . ?
C1 C2 C3 120.49(9) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.13(9) . . ?
O2 C3 C4 118.02(10) . . ?
C2 C3 C4 119.84(11) . . ?
C5 C4 C3 118.83(11) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.97(10) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.08(11) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.82(11) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 119.01(11) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 117.21(10) . . ?
C10 C9 N2A 121.2(9) . . ?
C8 C9 N2A 121.4(9) . . ?
C10 C9 C17 117.5(3) . . ?
C8 C9 C17 125.2(3) . . ?
C10 C9 N2B 150.7(8) . . ?
C8 C9 N2B 92.0(8) . . ?
C11 C10 C9 119.76(11) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N1 C11 C10 123.32(11) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C13 C12 C16 117.07(10) . . ?
C13 C12 N3A 120.7(10) . . ?
C16 C12 N3A 122.2(10) . . ?
C13 C12 C18 117.5(3) . . ?
C16 C12 C18 125.4(3) . . ?
C13 C12 N3B 154.3(7) . . ?
C16 C12 N3B 88.5(7) . . ?
C14 C13 C12 119.85(11) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
N4 C14 C13 123.67(11) . . ?
N4 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
N4 C15 C16 123.21(11) . . ?
N4 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C15 C16 C12 119.33(11) . . ?
C15 C16 H16 120.3 . . ?
C12 C16 H16 120.3 . . ?

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
O1 H1 N1 0.83 1.92 2.7500(12) 176.7 . yes
O2 H2A N4 0.83 1.93 2.7638(12) 177.4 2_667 yes

####################################################################### 
# 
# 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_A25_BE75_270
_database_code_depnum_ccdc_archive 'CCDC 1995479'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT077_A25_BE75_270        
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)ethylene molecules.
;
_vrf_PLAT155_A25_BE75_270        
;
PROBLEM: The Triclinic Unitcell is NOT Reduced ..........     Please Do !  
RESPONSE: The unit cell was not reduce to keep it consistent with the values 
          at other temperatures.
;
_vrf_PLAT911_A25_BE75_270        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2020-03-10T15:58:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C17.54 H15.54 N2.46 O2'
_chemical_formula_weight         292.78

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.10962(13)
_cell_length_b                   9.89822(18)
_cell_length_c                   10.89834(15)
_cell_angle_alpha                93.2450(18)
_cell_angle_beta                 107.0364(13)
_cell_angle_gamma                114.2057(13)
_cell_volume                     747.06(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    14206
_cell_measurement_theta_min      4.308
_cell_measurement_theta_max      75.685

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.085
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             308
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -6 0.0337
3 6 0 0.0565
-2 0 6 0.0536
1 6 1 0.0529
0 -6 -1 0.0564
5 2 3 0.1012
-5 -5 -1 0.093
0 6 4 0.0506
0 0 7 0.0473
-4 2 0 0.1051
1 -4 3 0.0582
-3 -4 3 0.0674
-1 -1 -7 0.0394
0 -3 5 0.0488
0 3 6 0.0455
-1 -4 -7 0.0412
-4 -4 -6 0.0836
-1 -6 -4 0.0452
3 6 4 0.0661
-3 3 -3 0.0956
-5 -2 -3 0.1148
4 5 1 0.0716


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.521
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.859
_shelx_estimated_absorpt_T_max   0.943

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      270(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0006697
_diffrn_orient_matrix_ub_12      0.0482059
_diffrn_orient_matrix_ub_13      -0.1481174
_diffrn_orient_matrix_ub_21      -0.0735467
_diffrn_orient_matrix_ub_22      0.167412
_diffrn_orient_matrix_ub_23      0.0101517
_diffrn_orient_matrix_ub_31      0.1992293
_diffrn_orient_matrix_ub_32      -0.0039657
_diffrn_orient_matrix_ub_33      -0.0274327
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_number            27405
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.333
_diffrn_reflns_theta_max         77.418
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.959
_reflns_Friedel_coverage         0
_reflns_number_total             3053
_reflns_number_gt                2643
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0623P)²+0.0687P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0042(9)
_refine_ls_number_reflns         3053
_refine_ls_number_parameters     242
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.031

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)ethylene and the pedal motion about the azo group, the atom 
 sites N2 and N3, were split into parts A and B. These sites were allowed to 
 free refine their site occupancies to a total value of 1. To help maintain 
 reasonable ADP and bond lengths, SIMU, RIGU, and DFIX restraints and 
 constraints were applied. At this temperature the ratio of 4,4'-azopyridine 
 to bis(4-pyridyl)ethylene was 0.17 to 0.77 with the amount of 
 4,4'-azopyridine in the secondary position calculated at 0.06. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16690(12) 0.15542(10) 0.30661(8) 0.0584(2) Uani 1 1 d . . . . .
H1 H 0.198638 0.181299 0.386091 0.088 Uiso 1 1 calc R U . . .
O2 O 0.82075(13) 0.22779(12) 0.43130(8) 0.0669(3) Uani 1 1 d . . . . .
H2A H 0.824716 0.263777 0.502361 0.1 Uiso 1 1 calc R U . . .
N1 N 0.26051(15) 0.24652(13) 0.57121(10) 0.0584(3) Uani 1 1 d . . . . .
N2A N 0.241(4) 0.385(3) 0.941(2) 0.047(2) Uani 0.167(3) 1 d D U P A 1
N3A N 0.274(5) 0.510(3) 0.997(2) 0.052(3) Uani 0.167(3) 1 d D U P A 1
C17 C 0.2132(9) 0.3774(7) 0.9340(5) 0.0472(9) Uani 0.771(3) 1 d D U P A 2
H17 H 0.156953 0.299836 0.974737 0.057 Uiso 0.771(3) 1 calc DR U P A 2
C18 C 0.2637(11) 0.5180(7) 0.9863(6) 0.0457(7) Uani 0.771(3) 1 d D U P A 2
H18 H 0.320333 0.595263 0.945435 0.055 Uiso 0.771(3) 1 calc R U P A 2
N2B N 0.269(2) 0.466(2) 0.9200(15) 0.050(3) Uani 0.0618(18) 1 d D U P A 3
N3B N 0.197(2) 0.410(2) 1.0029(16) 0.052(3) Uani 0.0618(18) 1 d D U P A 3
N4 N 0.17665(14) 0.65111(12) 1.33260(9) 0.0544(3) Uani 1 1 d . . . . .
C1 C 0.31733(17) 0.15246(11) 0.27775(10) 0.0470(3) Uani 1 1 d . . . . .
C2 C 0.49363(16) 0.19034(12) 0.37381(10) 0.0473(3) Uani 1 1 d . . . . .
H2 H 0.510476 0.217329 0.461346 0.057 Uiso 1 1 calc R U . . .
C3 C 0.64541(18) 0.18833(13) 0.34045(11) 0.0506(3) Uani 1 1 d . . . . .
C4 C 0.6192(2) 0.14487(14) 0.20943(12) 0.0574(3) Uani 1 1 d . . . . .
H4 H 0.719184 0.141537 0.186049 0.069 Uiso 1 1 calc R U . . .
C5 C 0.4428(2) 0.10703(14) 0.11538(11) 0.0597(3) Uani 1 1 d . . . . .
H5 H 0.425351 0.078758 0.027927 0.072 Uiso 1 1 calc R U . . .
C6 C 0.29116(19) 0.10976(13) 0.14685(11) 0.0555(3) Uani 1 1 d . . . . .
H6 H 0.173194 0.083461 0.081594 0.067 Uiso 1 1 calc R U . . .
C7 C 0.32174(19) 0.39260(15) 0.61995(12) 0.0594(3) Uani 1 1 d . . . . .
H7 H 0.369506 0.463088 0.570875 0.071 Uiso 1 1 calc R U . . .
C8 C 0.31816(19) 0.44458(14) 0.73832(12) 0.0563(3) Uani 1 1 d . . . . .
H8 H 0.364517 0.547607 0.768565 0.068 Uiso 1 1 calc R U . . .
C9 C 0.24415(16) 0.34076(13) 0.81225(11) 0.0488(3) Uani 1 1 d D . . . .
C10 C 0.18480(19) 0.19008(14) 0.76333(12) 0.0564(3) Uani 1 1 d . . . . .
H10 H 0.137957 0.117147 0.810747 0.068 Uiso 1 1 calc R U . . .
C11 C 0.19521(19) 0.14839(15) 0.64452(12) 0.0588(3) Uani 1 1 d . . . . .
H11 H 0.154588 0.046396 0.613624 0.071 Uiso 1 1 calc R U . . .
C12 C 0.23291(16) 0.55618(14) 1.10802(11) 0.0490(3) Uani 1 1 d D . . . .
C13 C 0.28621(18) 0.70602(14) 1.15271(12) 0.0569(3) Uani 1 1 d . . . . .
H13 H 0.342276 0.778773 1.107928 0.068 Uiso 1 1 calc R U . . .
C14 C 0.25655(19) 0.74787(14) 1.26331(12) 0.0591(3) Uani 1 1 d . . . . .
H14 H 0.29454 0.849975 1.29156 0.071 Uiso 1 1 calc R U . . .
C15 C 0.12342(18) 0.50520(14) 1.28980(11) 0.0543(3) Uani 1 1 d . . . . .
H15 H 0.066499 0.435213 1.336331 0.065 Uiso 1 1 calc R U . . .
C16 C 0.14893(18) 0.45318(14) 1.17947(12) 0.0541(3) Uani 1 1 d . . . . .
H16 H 0.110433 0.350587 1.15334 0.065 Uiso 1 1 calc DR U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3569(14) . ?
O1 H1 0.82 . ?
O2 C3 1.3530(15) . ?
O2 H2A 0.82 . ?
N1 C11 1.3327(17) . ?
N1 C7 1.3376(16) . ?
N2A N3A 1.234(10) . ?
N2A C9 1.453(18) . ?
N3A C12 1.442(18) . ?
C17 C18 1.317(4) . ?
C17 C9 1.473(5) . ?
C17 H17 0.93 . ?
C18 C12 1.477(4) . ?
C18 H18 0.93 . ?
N2B N3B 1.245(10) . ?
N2B C9 1.563(18) . ?
N3B C12 1.660(18) . ?
N4 C14 1.3293(17) . ?
N4 C15 1.3358(16) . ?
C1 C2 1.3855(16) . ?
C1 C6 1.3927(15) . ?
C2 C3 1.3890(17) . ?
C2 H2 0.93 . ?
C3 C4 1.3953(15) . ?
C4 C5 1.3766(19) . ?
C4 H4 0.93 . ?
C5 C6 1.3802(19) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.3744(17) . ?
C7 H7 0.93 . ?
C8 C9 1.3917(17) . ?
C8 H8 0.93 . ?
C9 C10 1.3826(17) . ?
C10 C11 1.3733(17) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 C13 1.3758(17) . ?
C12 C16 1.3931(17) . ?
C13 C14 1.3702(18) . ?
C13 H13 0.93 . ?
C14 H14 0.93 . ?
C15 C16 1.3845(17) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 116.71(10) . . ?
N3A N2A C9 130(2) . . ?
N2A N3A C12 133(2) . . ?
C18 C17 C9 121.3(5) . . ?
C18 C17 H17 119.4 . . ?
C9 C17 H17 119.4 . . ?
C17 C18 C12 121.8(5) . . ?
C17 C18 H18 119.1 . . ?
C12 C18 H18 119.1 . . ?
N3B N2B C9 112.0(17) . . ?
N2B N3B C12 105.9(15) . . ?
C14 N4 C15 116.81(10) . . ?
O1 C1 C2 122.12(9) . . ?
O1 C1 C6 118.15(11) . . ?
C2 C1 C6 119.74(11) . . ?
C1 C2 C3 120.53(10) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O2 C3 C2 122.16(10) . . ?
O2 C3 C4 118.02(11) . . ?
C2 C3 C4 119.82(11) . . ?
C5 C4 C3 118.82(12) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.05(10) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.03(12) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.81(12) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 119.02(12) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 117.18(11) . . ?
C10 C9 N2A 119.7(10) . . ?
C8 C9 N2A 122.9(10) . . ?
C10 C9 C17 117.4(3) . . ?
C8 C9 C17 125.3(3) . . ?
C10 C9 N2B 149.7(6) . . ?
C8 C9 N2B 93.1(6) . . ?
C11 C10 C9 119.82(11) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N1 C11 C10 123.40(12) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C13 C12 C16 117.03(11) . . ?
C13 C12 N3A 121.1(10) . . ?
C16 C12 N3A 121.8(10) . . ?
C13 C12 C18 117.2(3) . . ?
C16 C12 C18 125.7(3) . . ?
C13 C12 N3B 155.0(5) . . ?
C16 C12 N3B 87.9(5) . . ?
C14 C13 C12 119.89(11) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
N4 C14 C13 123.85(12) . . ?
N4 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
N4 C15 C16 123.14(11) . . ?
N4 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C15 C16 C12 119.28(11) . . ?
C15 C16 H16 120.4 . . ?
C12 C16 H16 120.4 . . ?

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
O1 H1 N1 0.82 1.93 2.7508(13) 176.3 . yes
O2 H2A N4 0.82 1.95 2.7669(13) 177.5 2_667 yes

####################################################################### 
# 
# 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_A50_BE50_250
_database_code_depnum_ccdc_archive 'CCDC 1995485'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT077_A50_BE50_250        
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)ethylene molecules within the structure.
;
_vrf_PLAT230_A50_BE50_250        
;
PROBLEM: Hirshfeld Test Diff for    C12      --C16      .        5.1 s.u.  
RESPONSE: Due to the pedal motion of the 4,4'-azopyridine molecule.
;
# end Validation Reply Form

_audit_creation_date             2020-03-05T13:02:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C17.04 H15.04 N2.96 O2'
_chemical_formula_weight         293.28

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.04836(15)
_cell_length_b                   9.83877(18)
_cell_length_c                   10.88786(18)
_cell_angle_alpha                93.5909(14)
_cell_angle_beta                 106.7035(16)
_cell_angle_gamma                113.9933(18)
_cell_volume                     738.39(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    11392
_cell_measurement_theta_min      4.308
_cell_measurement_theta_max      76.456

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.102
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             308
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -2 1 0.0681
3 3 -3 0.0873
0 6 -2 0.0863
4 1 -1 0.0905
-1 -2 -4 0.0457
0 -6 2 0.0494
2 2 -7 0.0731
-1 0 7 0.036
-2 1 -5 0.0681
0 4 -6 0.0553
3 0 4 0.092
4 -5 -3 0.1384
-3 6 2 0.1189
1 -3 -5 0.0535
0 0 -7 0.0505
-3 6 -2 0.1171


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.501
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.869
_shelx_estimated_absorpt_T_max   0.929

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      250(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.1316136
_diffrn_orient_matrix_ub_12      -0.0768229
_diffrn_orient_matrix_ub_13      0.0519159
_diffrn_orient_matrix_ub_21      0.0243496
_diffrn_orient_matrix_ub_22      0.0591271
_diffrn_orient_matrix_ub_23      0.1415476
_diffrn_orient_matrix_ub_31      -0.1784411
_diffrn_orient_matrix_ub_32      -0.1458328
_diffrn_orient_matrix_ub_33      -0.0071389
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.061
_diffrn_reflns_number            21652
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.332
_diffrn_reflns_theta_max         77.151
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.947
_reflns_Friedel_coverage         0
_reflns_number_total             2966
_reflns_number_gt                2431
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0559P)²+0.0995P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0054(9)
_refine_ls_number_reflns         2966
_refine_ls_number_parameters     242
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.032

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)ethylene and the pedal motion about the azo group, the atom 
 sites N2 and N3, were split into parts A and B. These sites were allowed to 
 free refine their site occupancies to a total value of 1. To help maintain 
 reasonable ADP and bond lengths, SIMU, RIGU, and DFIX restraints and 
 constraints were applied. At this temperature the ratio of 4,4'-azopyridine 
 to bis(4-pyridyl)ethylene was 0.48 to 0.52 with the amount of 
 4,4'-azopyridine in the secondary position calculated at 0.06. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16581(14) 0.15789(12) 0.30922(9) 0.0558(3) Uani 1 1 d . . . . .
H1 H 0.197668 0.183425 0.389776 0.084 Uiso 1 1 calc R U . . .
O2 O 0.82176(15) 0.22581(14) 0.43261(10) 0.0640(3) Uani 1 1 d . . . . .
H2A H 0.825245 0.262032 0.504752 0.096 Uiso 1 1 calc R U . . .
N1 N 0.26027(17) 0.24807(15) 0.57516(11) 0.0549(3) Uani 1 1 d . . . . .
N2A N 0.222(2) 0.3797(15) 0.9439(12) 0.0474(19) Uani 0.422(3) 1 d D U P A 1
N3A N 0.270(2) 0.5136(15) 0.9882(14) 0.049(2) Uani 0.422(3) 1 d D U P A 1
C17 C 0.212(2) 0.3769(14) 0.9343(12) 0.0455(16) Uani 0.519(3) 1 d D U P A 2
H17 H 0.155733 0.298651 0.976019 0.055 Uiso 0.519(3) 1 calc DR U P A 2
C18 C 0.263(2) 0.5185(14) 0.9844(13) 0.0434(14) Uani 0.519(3) 1 d D U P A 2
H18 H 0.318208 0.596656 0.942284 0.052 Uiso 0.519(3) 1 calc R U P A 2
N2B N 0.272(3) 0.468(3) 0.923(2) 0.048(3) Uani 0.059(2) 1 d D U P A 3
N3B N 0.189(3) 0.404(3) 0.998(2) 0.049(3) Uani 0.059(2) 1 d D U P A 3
N4 N 0.17652(16) 0.65066(14) 1.33047(11) 0.0521(3) Uani 1 1 d . . . . .
C1 C 0.3171(2) 0.15398(14) 0.27965(12) 0.0447(3) Uani 1 1 d . . . . .
C2 C 0.49337(19) 0.19047(14) 0.37567(12) 0.0453(3) Uani 1 1 d . . . . .
H2 H 0.509813 0.217322 0.464241 0.054 Uiso 1 1 calc R U . . .
C3 C 0.6463(2) 0.18759(15) 0.34175(12) 0.0478(3) Uani 1 1 d . . . . .
C4 C 0.6206(2) 0.14478(16) 0.21084(14) 0.0544(4) Uani 1 1 d . . . . .
H4 H 0.72197 0.140612 0.186928 0.065 Uiso 1 1 calc R U . . .
C5 C 0.4441(2) 0.10857(16) 0.11673(13) 0.0568(4) Uani 1 1 d . . . . .
H5 H 0.42685 0.080312 0.028215 0.068 Uiso 1 1 calc R U . . .
C6 C 0.2918(2) 0.11263(16) 0.14879(13) 0.0531(3) Uani 1 1 d . . . . .
H6 H 0.17276 0.087764 0.082998 0.064 Uiso 1 1 calc R U . . .
C7 C 0.3222(2) 0.39480(18) 0.62451(14) 0.0566(4) Uani 1 1 d . . . . .
H7 H 0.370998 0.466439 0.575155 0.068 Uiso 1 1 calc R U . . .
C8 C 0.3186(2) 0.44708(17) 0.74369(14) 0.0541(3) Uani 1 1 d . . . . .
H8 H 0.365793 0.551676 0.775117 0.065 Uiso 1 1 calc R U . . .
C9 C 0.24376(19) 0.34205(16) 0.81628(12) 0.0465(3) Uani 1 1 d D . . . .
C10 C 0.1832(2) 0.19042(17) 0.76720(14) 0.0533(3) Uani 1 1 d . . . . .
H10 H 0.134705 0.116318 0.814732 0.064 Uiso 1 1 calc R U . . .
C11 C 0.1946(2) 0.14913(17) 0.64800(14) 0.0554(4) Uani 1 1 d . . . . .
H11 H 0.153952 0.045622 0.616229 0.067 Uiso 1 1 calc R U . . .
C12 C 0.23217(19) 0.55437(16) 1.10578(12) 0.0472(3) Uani 1 1 d D . . . .
C13 C 0.2861(2) 0.70527(17) 1.14981(14) 0.0555(4) Uani 1 1 d . . . . .
H13 H 0.342513 0.778606 1.104035 0.067 Uiso 1 1 calc R U . . .
C14 C 0.2569(2) 0.74783(17) 1.26132(14) 0.0570(4) Uani 1 1 d . . . . .
H14 H 0.295921 0.851644 1.290412 0.068 Uiso 1 1 calc R U . . .
C15 C 0.1228(2) 0.50386(17) 1.28745(13) 0.0522(3) Uani 1 1 d . . . . .
H15 H 0.06529 0.433184 1.334776 0.063 Uiso 1 1 calc R U . . .
C16 C 0.1478(2) 0.45064(16) 1.17659(13) 0.0521(3) Uani 1 1 d . . . . .
H16 H 0.108352 0.346341 1.149694 0.063 Uiso 1 1 calc DR U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3603(16) . ?
O1 H1 0.83 . ?
O2 C3 1.3535(17) . ?
O2 H2A 0.83 . ?
N1 C11 1.332(2) . ?
N1 C7 1.3360(19) . ?
N2A N3A 1.231(8) . ?
N2A C9 1.493(11) . ?
N3A C12 1.465(12) . ?
C17 C18 1.313(7) . ?
C17 C9 1.426(11) . ?
C17 H17 0.94 . ?
C18 C12 1.459(10) . ?
C18 H18 0.94 . ?
N2B N3B 1.241(10) . ?
N2B C9 1.54(2) . ?
N3B C12 1.68(2) . ?
N4 C14 1.329(2) . ?
N4 C15 1.3356(18) . ?
C1 C2 1.3856(18) . ?
C1 C6 1.3892(18) . ?
C2 C3 1.3934(18) . ?
C2 H2 0.94 . ?
C3 C4 1.3912(18) . ?
C4 C5 1.379(2) . ?
C4 H4 0.94 . ?
C5 C6 1.382(2) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.378(2) . ?
C7 H7 0.94 . ?
C8 C9 1.387(2) . ?
C8 H8 0.94 . ?
C9 C10 1.3812(19) . ?
C10 C11 1.3751(19) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.375(2) . ?
C12 C16 1.390(2) . ?
C13 C14 1.373(2) . ?
C13 H13 0.94 . ?
C14 H14 0.94 . ?
C15 C16 1.3845(19) . ?
C15 H15 0.94 . ?
C16 H16 0.94 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 116.92(12) . . ?
N3A N2A C9 118.3(11) . . ?
N2A N3A C12 120.3(12) . . ?
C18 C17 C9 119.8(10) . . ?
C18 C17 H17 120.1 . . ?
C9 C17 H17 120.1 . . ?
C17 C18 C12 119.8(11) . . ?
C17 C18 H18 120.1 . . ?
C12 C18 H18 120.1 . . ?
N3B N2B C9 107(2) . . ?
N2B N3B C12 101(2) . . ?
C14 N4 C15 117.02(12) . . ?
O1 C1 C2 121.91(11) . . ?
O1 C1 C6 118.18(12) . . ?
C2 C1 C6 119.91(12) . . ?
C1 C2 C3 120.41(11) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C4 118.23(12) . . ?
O2 C3 C2 122.04(11) . . ?
C4 C3 C2 119.73(13) . . ?
C5 C4 C3 119.01(13) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.89(12) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.04(13) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.73(14) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.59(14) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C10 C9 C8 118.02(12) . . ?
C10 C9 C17 116.8(5) . . ?
C8 C9 C17 125.1(5) . . ?
C10 C9 N2A 116.9(5) . . ?
C8 C9 N2A 125.1(5) . . ?
C10 C9 N2B 150.4(8) . . ?
C8 C9 N2B 91.6(8) . . ?
C11 C10 C9 119.23(14) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C11 C10 123.47(14) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C13 C12 C16 117.89(12) . . ?
C13 C12 C18 115.8(5) . . ?
C16 C12 C18 126.3(5) . . ?
C13 C12 N3A 117.8(6) . . ?
C16 C12 N3A 124.3(6) . . ?
C13 C12 N3B 154.9(6) . . ?
C16 C12 N3B 86.9(6) . . ?
C14 C13 C12 119.34(14) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
N4 C14 C13 123.76(14) . . ?
N4 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
N4 C15 C16 123.23(13) . . ?
N4 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C15 C16 C12 118.75(13) . . ?
C15 C16 H16 120.6 . . ?
C12 C16 H16 120.6 . . ?

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
O1 H1 N1 0.83 1.93 2.7592(15) 176.4 . yes
O2 H2A N4 0.83 1.95 2.7757(14) 177.3 2_667 yes

####################################################################### 
# 
# 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_A25_BE75_230
_database_code_depnum_ccdc_archive 'CCDC 1995477'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT077_A25_BE75_230        
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)ethylene molecules.
;
_vrf_PLAT155_A25_BE75_230        
;
PROBLEM: The Triclinic Unitcell is NOT Reduced ..........     Please Do !  
RESPONSE: The unit cell was not reduce to keep it consistent with the values 
          at other temperatures.
;
_vrf_PLAT911_A25_BE75_230        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          8 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2020-03-10T15:57:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C17.55 H15.55 N2.45 O2'
_chemical_formula_weight         292.77

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.07233(10)
_cell_length_b                   9.87774(15)
_cell_length_c                   10.88779(14)
_cell_angle_alpha                93.0700(16)
_cell_angle_beta                 107.0652(11)
_cell_angle_gamma                114.2729(11)
_cell_volume                     741.293(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    15546
_cell_measurement_theta_min      4.307
_cell_measurement_theta_max      77.192

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.085
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             308
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -6 0.0337
3 6 0 0.0565
-2 0 6 0.0536
1 6 1 0.0529
0 -6 -1 0.0564
5 2 3 0.1012
-5 -5 -1 0.093
0 6 4 0.0506
0 0 7 0.0473
-4 2 0 0.1051
1 -4 3 0.0582
-3 -4 3 0.0674
-1 -1 -7 0.0394
0 -3 5 0.0488
0 3 6 0.0455
-1 -4 -6 0.0412
-4 -4 -5 0.0836
-1 -6 -4 0.0452
3 6 4 0.0661
-3 3 -3 0.0956
-5 -2 -3 0.1148
4 5 1 0.0716


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.858
_shelx_estimated_absorpt_T_max   0.942

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      230(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0004882
_diffrn_orient_matrix_ub_12      0.0477696
_diffrn_orient_matrix_ub_13      -0.148104
_diffrn_orient_matrix_ub_21      -0.0733325
_diffrn_orient_matrix_ub_22      0.1679051
_diffrn_orient_matrix_ub_23      0.0100898
_diffrn_orient_matrix_ub_31      0.2001872
_diffrn_orient_matrix_ub_32      -0.003876
_diffrn_orient_matrix_ub_33      -0.0279718
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_number            27752
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.335
_diffrn_reflns_theta_max         77.335
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.964
_reflns_Friedel_coverage         0
_reflns_number_total             3038
_reflns_number_gt                2721
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0605P)²+0.0803P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0041(9)
_refine_ls_number_reflns         3038
_refine_ls_number_parameters     242
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.108
_refine_ls_wR_factor_gt          0.1047
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.032

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)ethylene and the pedal motion about the azo group, the atom 
 sites N2 and N3, were split into parts A and B. These sites were allowed to 
 free refine their site occupancies to a total value of 1. To help maintain 
 reasonable ADP and bond lengths, SIMU, RIGU, and DFIX restraints and 
 constraints were applied. At this temperature the ratio of 4,4'-azopyridine 
 to bis(4-pyridyl)ethylene was 0.20 to 0.77 with the amount of 
 4,4'-azopyridine in the secondary position calculated at 0.03. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16609(11) 0.15717(9) 0.30653(7) 0.0482(2) Uani 1 1 d . . . . .
H1 H 0.198771 0.184278 0.386937 0.072 Uiso 1 1 calc R U . . .
O2 O 0.82282(12) 0.22830(10) 0.43188(8) 0.0551(2) Uani 1 1 d . . . . .
H2A H 0.827394 0.266018 0.503493 0.083 Uiso 1 1 calc R U . . .
N1 N 0.26084(14) 0.24708(12) 0.57126(9) 0.0492(2) Uani 1 1 d . . . . .
N2A N 0.234(4) 0.379(2) 0.941(2) 0.039(2) Uani 0.197(3) 1 d D U P A 1
N3A N 0.272(4) 0.507(2) 0.995(2) 0.043(3) Uani 0.197(3) 1 d D U P A 1
C17 C 0.2137(12) 0.3788(7) 0.9340(6) 0.0407(10) Uani 0.776(3) 1 d D U P A 2
H17 H 0.156133 0.300524 0.975558 0.049 Uiso 0.776(3) 1 calc DR U P A 2
C18 C 0.2645(11) 0.5196(7) 0.9867(6) 0.0379(7) Uani 0.776(3) 1 d D U P A 2
H18 H 0.322327 0.598214 0.94552 0.045 Uiso 0.776(3) 1 calc R U P A 2
N2B N 0.264(5) 0.464(4) 0.920(3) 0.042(3) Uani 0.0278(16) 1 d D U P A 3
N3B N 0.193(5) 0.412(4) 1.004(3) 0.044(3) Uani 0.0278(16) 1 d D U P A 3
N4 N 0.17555(13) 0.65118(11) 1.33267(9) 0.0458(2) Uani 1 1 d . . . . .
C1 C 0.31684(16) 0.15362(11) 0.27774(10) 0.0395(2) Uani 1 1 d . . . . .
C2 C 0.49423(16) 0.19161(11) 0.37414(9) 0.0397(2) Uani 1 1 d . . . . .
H2 H 0.511407 0.21933 0.46258 0.048 Uiso 1 1 calc R U . . .
C3 C 0.64682(16) 0.18898(12) 0.34089(10) 0.0422(3) Uani 1 1 d . . . . .
C4 C 0.62031(19) 0.14518(12) 0.20966(11) 0.0481(3) Uani 1 1 d . . . . .
H4 H 0.721795 0.141636 0.18614 0.058 Uiso 1 1 calc R U . . .
C5 C 0.44287(19) 0.10723(12) 0.11516(10) 0.0498(3) Uani 1 1 d . . . . .
H5 H 0.425042 0.078404 0.026766 0.06 Uiso 1 1 calc R U . . .
C6 C 0.29049(18) 0.11041(12) 0.14683(10) 0.0466(3) Uani 1 1 d . . . . .
H6 H 0.170642 0.083756 0.080865 0.056 Uiso 1 1 calc R U . . .
C7 C 0.32215(17) 0.39335(14) 0.62040(11) 0.0494(3) Uani 1 1 d . . . . .
H7 H 0.370728 0.465213 0.570944 0.059 Uiso 1 1 calc R U . . .
C8 C 0.31825(17) 0.44464(13) 0.73888(11) 0.0462(3) Uani 1 1 d . . . . .
H8 H 0.365162 0.548869 0.769628 0.055 Uiso 1 1 calc R U . . .
C9 C 0.24360(15) 0.33969(12) 0.81289(10) 0.0401(2) Uani 1 1 d D . . . .
C10 C 0.18391(17) 0.18828(13) 0.76348(11) 0.0468(3) Uani 1 1 d . . . . .
H10 H 0.135931 0.113898 0.811116 0.056 Uiso 1 1 calc R U . . .
C11 C 0.19529(17) 0.14750(13) 0.64428(11) 0.0496(3) Uani 1 1 d . . . . .
H11 H 0.154896 0.044472 0.612835 0.059 Uiso 1 1 calc R U . . .
C12 C 0.23350(15) 0.55736(12) 1.10772(10) 0.0397(2) Uani 1 1 d D . . . .
C13 C 0.28681(17) 0.70799(13) 1.15261(11) 0.0469(3) Uani 1 1 d . . . . .
H13 H 0.343675 0.782004 1.107342 0.056 Uiso 1 1 calc R U . . .
C14 C 0.25649(18) 0.74939(13) 1.26368(11) 0.0494(3) Uani 1 1 d . . . . .
H14 H 0.294988 0.852665 1.292531 0.059 Uiso 1 1 calc R U . . .
C15 C 0.12265(16) 0.50497(13) 1.28945(10) 0.0451(3) Uani 1 1 d . . . . .
H15 H 0.064762 0.433616 1.336344 0.054 Uiso 1 1 calc R U . . .
C16 C 0.14885(17) 0.45357(12) 1.17930(11) 0.0442(3) Uani 1 1 d . . . . .
H16 H 0.110031 0.349757 1.152909 0.053 Uiso 1 1 calc DR U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3558(13) . ?
O1 H1 0.83 . ?
O2 C3 1.3527(14) . ?
O2 H2A 0.83 . ?
N1 C11 1.3351(16) . ?
N1 C7 1.3389(15) . ?
N2A N3A 1.236(10) . ?
N2A C9 1.463(17) . ?
N3A C12 1.464(16) . ?
C17 C18 1.319(4) . ?
C17 C9 1.468(5) . ?
C17 H17 0.94 . ?
C18 C12 1.468(5) . ?
C18 H18 0.94 . ?
N2B N3B 1.244(10) . ?
N2B C9 1.57(4) . ?
N3B C12 1.64(4) . ?
N4 C14 1.3331(15) . ?
N4 C15 1.3386(15) . ?
C1 C2 1.3881(15) . ?
C1 C6 1.3933(14) . ?
C2 C3 1.3914(15) . ?
C2 H2 0.94 . ?
C3 C4 1.3974(15) . ?
C4 C5 1.3795(18) . ?
C4 H4 0.94 . ?
C5 C6 1.3830(18) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3743(16) . ?
C7 H7 0.94 . ?
C8 C9 1.3957(16) . ?
C8 H8 0.94 . ?
C9 C10 1.3883(15) . ?
C10 C11 1.3782(16) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.3820(16) . ?
C12 C16 1.3955(15) . ?
C13 C14 1.3757(16) . ?
C13 H13 0.94 . ?
C14 H14 0.94 . ?
C15 C16 1.3831(15) . ?
C15 H15 0.94 . ?
C16 H16 0.94 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 116.91(10) . . ?
N3A N2A C9 125.7(19) . . ?
N2A N3A C12 131.1(19) . . ?
C18 C17 C9 122.5(5) . . ?
C18 C17 H17 118.8 . . ?
C9 C17 H17 118.8 . . ?
C17 C18 C12 122.0(5) . . ?
C17 C18 H18 119 . . ?
C12 C18 H18 119 . . ?
N3B N2B C9 113(3) . . ?
N2B N3B C12 106(3) . . ?
C14 N4 C15 116.85(10) . . ?
O1 C1 C2 122.04(9) . . ?
O1 C1 C6 118.21(10) . . ?
C2 C1 C6 119.75(10) . . ?
C1 C2 C3 120.52(9) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O2 C3 C2 122.15(9) . . ?
O2 C3 C4 118.09(10) . . ?
C2 C3 C4 119.76(10) . . ?
C5 C4 C3 118.96(11) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.84(10) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.17(11) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N1 C7 C8 123.87(11) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 119.03(11) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 117.17(10) . . ?
C10 C9 N2A 118.2(8) . . ?
C8 C9 N2A 124.5(8) . . ?
C10 C9 C17 118.7(3) . . ?
C8 C9 C17 124.0(3) . . ?
C10 C9 N2B 149.8(11) . . ?
C8 C9 N2B 93.0(11) . . ?
C11 C10 C9 119.72(11) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N1 C11 C10 123.25(11) . . ?
N1 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
C13 C12 C16 116.98(10) . . ?
C13 C12 N3A 122.5(8) . . ?
C16 C12 N3A 120.5(8) . . ?
C13 C12 C18 117.4(3) . . ?
C16 C12 C18 125.6(3) . . ?
C13 C12 N3B 155.7(10) . . ?
C16 C12 N3B 87.0(10) . . ?
C14 C13 C12 119.87(10) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
N4 C14 C13 123.64(11) . . ?
N4 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
N4 C15 C16 123.33(10) . . ?
N4 C15 H15 118.3 . . ?
C16 C15 H15 118.3 . . ?
C15 C16 C12 119.33(10) . . ?
C15 C16 H16 120.3 . . ?
C12 C16 H16 120.3 . . ?

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
O1 H1 N1 0.83 1.92 2.7485(12) 176.8 . yes
O2 H2A N4 0.83 1.93 2.7622(12) 177.2 2_667 yes

####################################################################### 
# 
# 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_A50_BE50_190
_database_code_depnum_ccdc_archive 'CCDC 1995482'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT077_A50_BE50_190        
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)ethylene molecules within the structure. 
;
_vrf_PLAT155_A50_BE50_190        
;
PROBLEM: The Triclinic Unitcell is NOT Reduced ..........     Please Do !  
RESPONSE: To keep the unit cell values consistent over the temperature 
          range studied.
;
# end Validation Reply Form

_audit_creation_date             2020-03-05T13:00:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C17.08 H15.08 N2.92 O2'
_chemical_formula_weight         293.24

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.99695(15)
_cell_length_b                   9.8077(3)
_cell_length_c                   10.8728(2)
_cell_angle_alpha                93.323(3)
_cell_angle_beta                 106.8183(17)
_cell_angle_gamma                114.090(2)
_cell_volume                     729.91(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    13578
_cell_measurement_theta_min      4.317
_cell_measurement_theta_max      76.991

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.102
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             308
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 6 1 0.0681
0 6 2 0.0494
-4 -5 -1 0.0905
0 -6 -2 0.0863
3 -3 -2 0.1171
1 1 7 0.036
1 3 -4 0.0457
-2 -4 -7 0.0731
-3 -6 -3 0.0873
2 1 -5 0.0681
0 -3 -6 0.0553
-3 -2 4 0.092
3 -3 2 0.1189
-4 1 -3 0.1384
-1 3 -5 0.0535
0 0 -7 0.0505


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.362
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.929

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      190(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.2095436
_diffrn_orient_matrix_ub_12      0.0769724
_diffrn_orient_matrix_ub_13      0.0525786
_diffrn_orient_matrix_ub_21      0.0348092
_diffrn_orient_matrix_ub_22      -0.0595411
_diffrn_orient_matrix_ub_23      0.1415234
_diffrn_orient_matrix_ub_31      0.0334703
_diffrn_orient_matrix_ub_32      0.1462475
_diffrn_orient_matrix_ub_33      -0.0066256
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_number            23005
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.337
_diffrn_reflns_theta_max         77.34
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.961
_reflns_Friedel_coverage         0
_reflns_number_total             2976
_reflns_number_gt                2596
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0588P)²+0.1041P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0045(9)
_refine_ls_number_reflns         2976
_refine_ls_number_parameters     242
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.037
_refine_ls_wR_factor_ref         0.109
_refine_ls_wR_factor_gt          0.1024
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)ethylene and the pedal motion about the azo group, the atom 
 sites N2 and N3, were split into parts A and B. These sites were allowed to 
 free refine their site occupancies to a total value of 1. To help maintain 
 reasonable ADP and bond lengths, SIMU, RIGU, and DFIX restraints and 
 constraints were applied. At this temperature the ratio of 4,4'-azopyridine 
 to bis(4-pyridyl)ethylene was 0.20 to 0.80, respectively. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16455(12) 0.15995(10) 0.30914(8) 0.0415(2) Uani 1 1 d . . . . .
H1 H 0.196636 0.184451 0.390837 0.062 Uiso 1 1 calc R U . . .
O2 O 0.82475(13) 0.22656(11) 0.43342(8) 0.0475(3) Uani 1 1 d . . . . .
H2A H 0.829753 0.266094 0.505843 0.071 Uiso 1 1 calc R U . . .
N1 N 0.26076(15) 0.24851(13) 0.57515(10) 0.0424(3) Uani 1 1 d . . . . .
N2A N 0.219(2) 0.3785(12) 0.9438(11) 0.0362(18) Uani 0.441(3) 1 d D U P A 1
N3A N 0.268(2) 0.5145(12) 0.9837(11) 0.0355(16) Uani 0.441(3) 1 d D U P A 1
C17 C 0.214(2) 0.3773(11) 0.9350(11) 0.0346(15) Uani 0.542(3) 1 d D U P A 2
H17 H 0.154463 0.297118 0.976179 0.042 Uiso 0.542(3) 1 calc DR U P A 2
C18 C 0.2657(18) 0.5191(11) 0.9893(10) 0.0348(15) Uani 0.542(3) 1 d D U P A 2
H18 H 0.32747 0.599406 0.949079 0.042 Uiso 0.542(3) 1 calc R U P A 2
N2B N 0.274(9) 0.465(8) 0.921(6) 0.037(3) Uani 0.0168(18) 1 d D U P A 3
N3B N 0.183(8) 0.407(7) 0.994(6) 0.037(3) Uani 0.0168(18) 1 d D U P A 3
N4 N 0.17514(14) 0.65071(12) 1.33044(9) 0.0403(2) Uani 1 1 d . . . . .
C1 C 0.31635(17) 0.15568(12) 0.27958(11) 0.0345(3) Uani 1 1 d . . . . .
C2 C 0.49414(17) 0.19199(12) 0.37611(10) 0.0345(3) Uani 1 1 d . . . . .
H2 H 0.511165 0.219525 0.465674 0.041 Uiso 1 1 calc R U . . .
C3 C 0.64765(17) 0.18821(13) 0.34218(11) 0.0365(3) Uani 1 1 d . . . . .
C4 C 0.62185(19) 0.14474(14) 0.21100(12) 0.0413(3) Uani 1 1 d . . . . .
H4 H 0.724838 0.139891 0.187098 0.05 Uiso 1 1 calc R U . . .
C5 C 0.4439(2) 0.10886(14) 0.11645(11) 0.0429(3) Uani 1 1 d . . . . .
H5 H 0.426269 0.080275 0.026945 0.052 Uiso 1 1 calc R U . . .
C6 C 0.29027(19) 0.11335(14) 0.14833(11) 0.0405(3) Uani 1 1 d . . . . .
H6 H 0.169015 0.087953 0.081699 0.049 Uiso 1 1 calc R U . . .
C7 C 0.32306(18) 0.39591(15) 0.62511(12) 0.0430(3) Uani 1 1 d . . . . .
H7 H 0.373062 0.469156 0.575481 0.052 Uiso 1 1 calc R U . . .
C8 C 0.31875(18) 0.44734(14) 0.74441(12) 0.0405(3) Uani 1 1 d . . . . .
H8 H 0.366204 0.553192 0.776303 0.049 Uiso 1 1 calc R U . . .
C9 C 0.24333(16) 0.34071(13) 0.81706(11) 0.0346(3) Uani 1 1 d D . . . .
C10 C 0.18208(18) 0.18808(14) 0.76742(12) 0.0400(3) Uani 1 1 d . . . . .
H10 H 0.132452 0.112371 0.815216 0.048 Uiso 1 1 calc R U . . .
C11 C 0.19422(18) 0.14772(15) 0.64758(12) 0.0419(3) Uani 1 1 d . . . . .
H11 H 0.153192 0.043042 0.615075 0.05 Uiso 1 1 calc R U . . .
C12 C 0.23269(16) 0.55575(14) 1.10532(11) 0.0349(3) Uani 1 1 d D . . . .
C13 C 0.28728(18) 0.70797(14) 1.14973(12) 0.0414(3) Uani 1 1 d . . . . .
H13 H 0.345256 0.782757 1.103701 0.05 Uiso 1 1 calc R U . . .
C14 C 0.25663(19) 0.75013(14) 1.26170(12) 0.0434(3) Uani 1 1 d . . . . .
H14 H 0.295496 0.855117 1.291208 0.052 Uiso 1 1 calc R U . . .
C15 C 0.12140(18) 0.50329(14) 1.28702(11) 0.0398(3) Uani 1 1 d . . . . .
H15 H 0.062469 0.431015 1.334558 0.048 Uiso 1 1 calc R U . . .
C16 C 0.14749(17) 0.45100(14) 1.17619(12) 0.0387(3) Uani 1 1 d . . . . .
H16 H 0.107904 0.345419 1.149029 0.046 Uiso 1 1 calc DR U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3581(14) . ?
O1 H1 0.84 . ?
O2 C3 1.3566(14) . ?
O2 H2A 0.84 . ?
N1 C11 1.3356(17) . ?
N1 C7 1.3408(16) . ?
N2A N3A 1.237(7) . ?
N2A C9 1.493(10) . ?
N3A C12 1.494(10) . ?
C17 C18 1.321(7) . ?
C17 C9 1.422(10) . ?
C17 H17 0.95 . ?
C18 C12 1.417(10) . ?
C18 H18 0.95 . ?
N2B N3B 1.240(10) . ?
N2B C9 1.50(7) . ?
N3B C12 1.68(7) . ?
N4 C14 1.3349(17) . ?
N4 C15 1.3395(16) . ?
C1 C2 1.3891(16) . ?
C1 C6 1.3931(16) . ?
C2 C3 1.3936(16) . ?
C2 H2 0.95 . ?
C3 C4 1.3950(16) . ?
C4 C5 1.3818(18) . ?
C4 H4 0.95 . ?
C5 C6 1.3853(18) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.3793(17) . ?
C7 H7 0.95 . ?
C8 C9 1.3921(18) . ?
C8 H8 0.95 . ?
C9 C10 1.3881(16) . ?
C10 C11 1.3815(17) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
C12 C13 1.3839(17) . ?
C12 C16 1.3919(17) . ?
C13 C14 1.3821(18) . ?
C13 H13 0.95 . ?
C14 H14 0.95 . ?
C15 C16 1.3856(17) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 117.11(10) . . ?
N3A N2A C9 116.3(9) . . ?
N2A N3A C12 118.0(10) . . ?
C18 C17 C9 122.2(9) . . ?
C18 C17 H17 118.9 . . ?
C9 C17 H17 118.9 . . ?
C17 C18 C12 122.4(9) . . ?
C17 C18 H18 118.8 . . ?
C12 C18 H18 118.8 . . ?
N3B N2B C9 109(6) . . ?
N2B N3B C12 104(6) . . ?
C14 N4 C15 117.34(10) . . ?
O1 C1 C2 121.80(10) . . ?
O1 C1 C6 118.25(10) . . ?
C2 C1 C6 119.94(11) . . ?
C1 C2 C3 120.30(10) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 121.95(10) . . ?
O2 C3 C4 118.06(11) . . ?
C2 C3 C4 119.99(11) . . ?
C5 C4 C3 118.82(11) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.95(10) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.99(11) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.79(12) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.53(12) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C10 C9 C8 118.11(11) . . ?
C10 C9 C17 117.8(4) . . ?
C8 C9 C17 124.0(4) . . ?
C10 C9 N2A 117.4(4) . . ?
C8 C9 N2A 124.5(4) . . ?
C10 C9 N2B 151(2) . . ?
C8 C9 N2B 91(2) . . ?
C11 C10 C9 119.13(11) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C11 C10 123.29(11) . . ?
N1 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
C13 C12 C16 117.89(11) . . ?
C13 C12 C18 116.8(4) . . ?
C16 C12 C18 125.3(4) . . ?
C13 C12 N3A 117.8(4) . . ?
C16 C12 N3A 124.3(4) . . ?
C13 C12 N3B 154.0(18) . . ?
C16 C12 N3B 87.4(18) . . ?
C14 C13 C12 119.34(12) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
N4 C14 C13 123.28(12) . . ?
N4 C14 H14 118.4 . . ?
C13 C14 H14 118.4 . . ?
N4 C15 C16 123.25(11) . . ?
N4 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C15 C16 C12 118.89(11) . . ?
C15 C16 H16 120.6 . . ?
C12 C16 H16 120.6 . . ?

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
O1 H1 N1 0.84 1.92 2.7544(13) 176.2 . yes
O2 H2A N4 0.84 1.93 2.7713(13) 176.6 2_667 yes

####################################################################### 
# 
# 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_A25_BE75_290
_database_code_depnum_ccdc_archive 'CCDC 1995480'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT077_A25_BE75_290        
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)ethylene molecules.
;
_vrf_PLAT230_A25_BE75_290        
;
PROBLEM: Hirshfeld Test Diff for    C12      --C16      .        6.9 s.u.  
RESPONSE: Due to slight positional disorder about the rings related to the 
          pedal motion in the structure.
;
_vrf_PLAT911_A25_BE75_290        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          9 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2020-03-10T15:59:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C17.54 H15.54 N2.46 O2'
_chemical_formula_weight         292.78

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.13099(12)
_cell_length_b                   9.90773(12)
_cell_length_c                   10.90319(14)
_cell_angle_alpha                93.3530(10)
_cell_angle_beta                 107.0207(13)
_cell_angle_gamma                114.1614(13)
_cell_volume                     750.133(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    13314
_cell_measurement_theta_min      4.305
_cell_measurement_theta_max      76.674

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.085
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             308
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 -6 0.0337
-3 -3 0 0.0565
2 -1 6 0.0536
-1 -5 1 0.0529
0 6 -1 0.0564
-5 3 3 0.1012
5 0 -1 0.093
0 -5 4 0.0506
0 0 7 0.0473
4 -6 0 0.1051
-1 5 3 0.0582
3 0 3 0.0674
1 0 -7 0.0394
0 3 5 0.0488
0 -3 6 0.0455
1 3 -7 0.0412
4 0 -6 0.0836
1 5 -4 0.0452
-3 -3 4 0.0661
3 -6 -3 0.0956
5 -3 -3 0.1148
-5 -1 1 0.0716


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.651
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.859
_shelx_estimated_absorpt_T_max   0.943

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      290(2)
_diffrn_ambient_environment      air
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0494613
_diffrn_orient_matrix_ub_12      -0.0484487
_diffrn_orient_matrix_ub_13      -0.1481812
_diffrn_orient_matrix_ub_21      -0.0934682
_diffrn_orient_matrix_ub_22      -0.1671676
_diffrn_orient_matrix_ub_23      0.0101577
_diffrn_orient_matrix_ub_31      -0.1945979
_diffrn_orient_matrix_ub_32      0.0040927
_diffrn_orient_matrix_ub_33      -0.0269431
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_number            26809
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.332
_diffrn_reflns_theta_max         77.306
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.96
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.96
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.96
_reflns_Friedel_coverage         0
_reflns_number_total             3064
_reflns_number_gt                2598
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0588P)²+0.1041P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0039(8)
_refine_ls_number_reflns         3064
_refine_ls_number_parameters     242
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.1081
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.948
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.03

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)ethylene and the pedal motion about the azo group, the atom 
 sites N2 and N3, were split into parts A and B. These sites were allowed to 
 free refine their site occupancies to a total value of 1. To help maintain 
 reasonable ADP and bond lengths, SIMU, RIGU, and DFIX restraints and 
 constraints were applied. At this temperature the ratio of 4,4'-azopyridine 
 to bis(4-pyridyl)ethylene was 0.14 to 0.77 with the amount of 
 4,4'-azopyridine in the secondary position calculated at 0.09. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16725(13) 0.15419(11) 0.30654(9) 0.0638(3) Uani 1 1 d . . . . .
H1 H 0.199338 0.181103 0.385938 0.096 Uiso 1 1 calc R U . . .
O2 O 0.81968(14) 0.22732(13) 0.43102(9) 0.0729(3) Uani 1 1 d . . . . .
H2A H 0.823285 0.262306 0.50234 0.109 Uiso 1 1 calc R U . . .
N1 N 0.26014(16) 0.24608(14) 0.57109(10) 0.0631(3) Uani 1 1 d . . . . .
N2A N 0.243(5) 0.386(3) 0.941(2) 0.049(3) Uani 0.144(3) 1 d D U P A 1
N3A N 0.276(6) 0.511(3) 0.997(3) 0.054(3) Uani 0.144(3) 1 d D U P A 1
C17 C 0.2139(9) 0.3776(7) 0.9339(5) 0.0517(10) Uani 0.771(3) 1 d D U P A 2
H17 H 0.158665 0.299849 0.974617 0.062 Uiso 0.771(3) 1 calc DR U P A 2
C18 C 0.2630(12) 0.5171(7) 0.9863(6) 0.0500(8) Uani 0.771(3) 1 d D U P A 2
H18 H 0.318707 0.594434 0.945393 0.06 Uiso 0.771(3) 1 calc R U P A 2
N2B N 0.2705(19) 0.4654(17) 0.9190(12) 0.054(2) Uani 0.085(2) 1 d D U P A 3
N3B N 0.1978(19) 0.4111(16) 1.0015(13) 0.056(2) Uani 0.085(2) 1 d D U P A 3
N4 N 0.17718(15) 0.65107(13) 1.33265(10) 0.0588(3) Uani 1 1 d . . . . .
C1 C 0.31748(18) 0.15164(12) 0.27761(11) 0.0510(3) Uani 1 1 d . . . . .
C2 C 0.49310(18) 0.18962(13) 0.37364(11) 0.0515(3) Uani 1 1 d . . . . .
H2 H 0.509811 0.216523 0.461165 0.062 Uiso 1 1 calc R U . . .
C3 C 0.64460(19) 0.18783(14) 0.34023(12) 0.0548(3) Uani 1 1 d . . . . .
C4 C 0.6187(2) 0.14484(15) 0.20937(13) 0.0625(3) Uani 1 1 d . . . . .
H4 H 0.718529 0.141893 0.185967 0.075 Uiso 1 1 calc R U . . .
C5 C 0.4429(2) 0.10684(15) 0.11542(12) 0.0650(4) Uani 1 1 d . . . . .
H5 H 0.425596 0.078729 0.02796 0.078 Uiso 1 1 calc R U . . .
C6 C 0.2916(2) 0.10913(14) 0.14694(12) 0.0601(3) Uani 1 1 d . . . . .
H6 H 0.173838 0.082612 0.081697 0.072 Uiso 1 1 calc R U . . .
C7 C 0.3216(2) 0.39226(16) 0.61965(13) 0.0648(3) Uani 1 1 d . . . . .
H7 H 0.369331 0.462391 0.570519 0.078 Uiso 1 1 calc R U . . .
C8 C 0.3182(2) 0.44467(15) 0.73785(13) 0.0617(3) Uani 1 1 d . . . . .
H8 H 0.364554 0.547679 0.76795 0.074 Uiso 1 1 calc R U . . .
C9 C 0.24456(18) 0.34148(15) 0.81191(11) 0.0538(3) Uani 1 1 d D . . . .
C10 C 0.1853(2) 0.19123(15) 0.76319(13) 0.0615(3) Uani 1 1 d . . . . .
H10 H 0.13847 0.11869 0.810717 0.074 Uiso 1 1 calc R U . . .
C11 C 0.1953(2) 0.14883(16) 0.64474(13) 0.0641(3) Uani 1 1 d . . . . .
H11 H 0.154605 0.046799 0.614159 0.077 Uiso 1 1 calc R U . . .
C12 C 0.23265(17) 0.55540(15) 1.10815(11) 0.0544(3) Uani 1 1 d D . . . .
C13 C 0.2855(2) 0.70449(15) 1.15269(13) 0.0627(3) Uani 1 1 d . . . . .
H13 H 0.34102 0.776895 1.107678 0.075 Uiso 1 1 calc R U . . .
C14 C 0.2569(2) 0.74700(15) 1.26317(13) 0.0645(3) Uani 1 1 d . . . . .
H14 H 0.295525 0.849174 1.291395 0.077 Uiso 1 1 calc R U . . .
C15 C 0.12361(19) 0.50527(15) 1.28989(12) 0.0590(3) Uani 1 1 d . . . . .
H15 H 0.066553 0.435588 1.336355 0.071 Uiso 1 1 calc R U . . .
C16 C 0.1489(2) 0.45289(15) 1.17976(13) 0.0596(3) Uani 1 1 d . . . . .
H16 H 0.110419 0.350336 1.153748 0.072 Uiso 1 1 calc DR U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3572(15) . ?
O1 H1 0.82 . ?
O2 C3 1.3540(16) . ?
O2 H2A 0.82 . ?
N1 C11 1.3319(18) . ?
N1 C7 1.3382(18) . ?
N2A N3A 1.234(10) . ?
N2A C9 1.454(19) . ?
N3A C12 1.444(19) . ?
C17 C18 1.311(3) . ?
C17 C9 1.474(5) . ?
C17 H17 0.93 . ?
C18 C12 1.476(4) . ?
C18 H18 0.93 . ?
N2B N3B 1.247(10) . ?
N2B C9 1.547(14) . ?
N3B C12 1.661(15) . ?
N4 C14 1.3284(18) . ?
N4 C15 1.3346(17) . ?
C1 C2 1.3841(17) . ?
C1 C6 1.3904(16) . ?
C2 C3 1.3893(18) . ?
C2 H2 0.93 . ?
C3 C4 1.3932(17) . ?
C4 C5 1.375(2) . ?
C4 H4 0.93 . ?
C5 C6 1.380(2) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.3729(19) . ?
C7 H7 0.93 . ?
C8 C9 1.3909(19) . ?
C8 H8 0.93 . ?
C9 C10 1.3786(18) . ?
C10 C11 1.3701(18) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 C13 1.3699(19) . ?
C12 C16 1.3938(19) . ?
C13 C14 1.3667(19) . ?
C13 H13 0.93 . ?
C14 H14 0.93 . ?
C15 C16 1.3829(18) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 116.60(11) . . ?
N3A N2A C9 130(2) . . ?
N2A N3A C12 132(2) . . ?
C18 C17 C9 121.3(5) . . ?
C18 C17 H17 119.4 . . ?
C9 C17 H17 119.4 . . ?
C17 C18 C12 122.1(5) . . ?
C17 C18 H18 119 . . ?
C12 C18 H18 119 . . ?
N3B N2B C9 112.2(14) . . ?
N2B N3B C12 107.0(12) . . ?
C14 N4 C15 116.66(11) . . ?
O1 C1 C2 122.06(10) . . ?
O1 C1 C6 118.18(12) . . ?
C2 C1 C6 119.76(12) . . ?
C1 C2 C3 120.48(11) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.23(10) . . ?
O2 C3 C4 117.95(12) . . ?
C2 C3 C4 119.82(12) . . ?
C5 C4 C3 118.86(13) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.01(11) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.06(13) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.77(13) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 119.04(13) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 117.14(12) . . ?
C10 C9 N2A 119.6(12) . . ?
C8 C9 N2A 123.1(12) . . ?
C10 C9 C17 117.1(3) . . ?
C8 C9 C17 125.7(3) . . ?
C10 C9 N2B 149.7(5) . . ?
C8 C9 N2B 93.1(5) . . ?
C11 C10 C9 119.97(13) . . ?
C11 C10 H10 120 . . ?
C9 C10 H10 120 . . ?
N1 C11 C10 123.44(13) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C13 C12 C16 116.89(12) . . ?
C13 C12 N3A 120.4(12) . . ?
C16 C12 N3A 122.6(12) . . ?
C13 C12 C18 117.2(3) . . ?
C16 C12 C18 125.9(3) . . ?
C13 C12 N3B 154.2(4) . . ?
C16 C12 N3B 88.8(4) . . ?
C14 C13 C12 120.10(13) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
N4 C14 C13 123.91(13) . . ?
N4 C14 H14 118 . . ?
C13 C14 H14 118 . . ?
N4 C15 C16 123.12(12) . . ?
N4 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C15 C16 C12 119.31(12) . . ?
C15 C16 H16 120.3 . . ?
C12 C16 H16 120.3 . . ?

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
O1 H1 N1 0.82 1.93 2.7520(14) 176.3 . yes
O2 H2A N4 0.82 1.95 2.7685(13) 177.2 2_667 yes

####################################################################### 
# 
# 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_A50_BE50_230
_database_code_depnum_ccdc_archive 'CCDC 1995484'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT077_A50_BE50_230        
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)ethylene molecules within the structure.
;
# end Validation Reply Form

_audit_creation_date             2020-03-05T13:01:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C17.09 H15.09 N2.91 O2'
_chemical_formula_weight         293.23

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.03047(14)
_cell_length_b                   9.82913(17)
_cell_length_c                   10.88163(17)
_cell_angle_alpha                93.5015(14)
_cell_angle_beta                 106.7347(15)
_cell_angle_gamma                114.0289(17)
_cell_volume                     735.48(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    12143
_cell_measurement_theta_min      4.296
_cell_measurement_theta_max      77.245

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.102
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             308
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -1 1 0.0681
3 3 -3 0.0873
0 6 -2 0.0863
4 1 -1 0.0905
-1 -2 -4 0.0457
0 -6 2 0.0494
2 2 -7 0.0731
-1 0 7 0.036
-2 1 -5 0.0681
0 4 -6 0.0553
3 0 4 0.092
4 -5 -3 0.1384
-3 6 2 0.1189
1 -3 -5 0.0535
0 0 -7 0.0505
-3 6 -2 0.1171


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.723
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.501
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.869
_shelx_estimated_absorpt_T_max   0.929

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      230(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.1318913
_diffrn_orient_matrix_ub_12      -0.0769762
_diffrn_orient_matrix_ub_13      0.0518666
_diffrn_orient_matrix_ub_21      0.0247897
_diffrn_orient_matrix_ub_22      0.0591716
_diffrn_orient_matrix_ub_23      0.1416526
_diffrn_orient_matrix_ub_31      -0.1788721
_diffrn_orient_matrix_ub_32      -0.1459417
_diffrn_orient_matrix_ub_33      -0.0069018
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_number            22021
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.334
_diffrn_reflns_theta_max         77.346
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.954
_reflns_Friedel_coverage         0
_reflns_number_total             2979
_reflns_number_gt                2505
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0548P)²+0.1088P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0047(8)
_refine_ls_number_reflns         2979
_refine_ls_number_parameters     242
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.039
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.033

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)ethylene and the pedal motion about the azo group, the atom 
 sites N2 and N3, were split into parts A and B. These sites were allowed to 
 free refine their site occupancies to a total value of 1. To help maintain 
 reasonable ADP and bond lengths, SIMU, RIGU, and DFIX restraints and 
 constraints were applied. At this temperature the ratio of 4,4'-azopyridine 
 to bis(4-pyridyl)ethylene was 0.46 to 0.54 with the amount of 
 4,4'-azopyridine in the secondary position calculated at 0.04. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16537(13) 0.15867(11) 0.30913(9) 0.0504(3) Uani 1 1 d . . . . .
H1 H 0.196728 0.182987 0.389789 0.076 Uiso 1 1 calc R U . . .
O2 O 0.82284(14) 0.22612(13) 0.43286(9) 0.0579(3) Uani 1 1 d . . . . .
H2A H 0.828478 0.266325 0.504224 0.087 Uiso 1 1 calc R U . . .
N1 N 0.26047(17) 0.24819(14) 0.57517(11) 0.0504(3) Uani 1 1 d . . . . .
N2A N 0.220(3) 0.3761(15) 0.9431(13) 0.0416(17) Uani 0.416(3) 1 d D U P A 1
N3A N 0.268(2) 0.5106(15) 0.9854(14) 0.0425(18) Uani 0.416(3) 1 d D U P A 1
C17 C 0.214(2) 0.3798(14) 0.9357(12) 0.0421(15) Uani 0.544(3) 1 d D U P A 2
H17 H 0.155841 0.301901 0.977623 0.051 Uiso 0.544(3) 1 calc DR U P A 2
C18 C 0.265(2) 0.5214(14) 0.9868(13) 0.0405(13) Uani 0.544(3) 1 d D U P A 2
H18 H 0.322957 0.600334 0.94593 0.049 Uiso 0.544(3) 1 calc R U P A 2
N2B N 0.272(4) 0.465(4) 0.920(3) 0.043(3) Uani 0.0398(19) 1 d D U P A 3
N3B N 0.197(4) 0.412(4) 1.002(3) 0.045(3) Uani 0.0398(19) 1 d D U P A 3
N4 N 0.17604(16) 0.65058(13) 1.33058(10) 0.0477(3) Uani 1 1 d . . . . .
C1 C 0.31687(19) 0.15470(13) 0.27971(12) 0.0408(3) Uani 1 1 d . . . . .
C2 C 0.49359(18) 0.19103(14) 0.37567(11) 0.0414(3) Uani 1 1 d . . . . .
H2 H 0.510178 0.217985 0.464276 0.05 Uiso 1 1 calc R U . . .
C3 C 0.64663(19) 0.18794(14) 0.34195(12) 0.0437(3) Uani 1 1 d . . . . .
C4 C 0.6210(2) 0.14479(15) 0.21093(13) 0.0499(3) Uani 1 1 d . . . . .
H4 H 0.722594 0.140358 0.187129 0.06 Uiso 1 1 calc R U . . .
C5 C 0.4441(2) 0.10870(16) 0.11679(13) 0.0519(3) Uani 1 1 d . . . . .
H5 H 0.426817 0.080426 0.028259 0.062 Uiso 1 1 calc R U . . .
C6 C 0.2913(2) 0.11285(15) 0.14868(12) 0.0485(3) Uani 1 1 d . . . . .
H6 H 0.171885 0.087764 0.082821 0.058 Uiso 1 1 calc R U . . .
C7 C 0.3224(2) 0.39510(17) 0.62484(14) 0.0517(3) Uani 1 1 d . . . . .
H7 H 0.371445 0.467019 0.575553 0.062 Uiso 1 1 calc R U . . .
C8 C 0.3186(2) 0.44722(16) 0.74390(13) 0.0490(3) Uani 1 1 d . . . . .
H8 H 0.365432 0.551841 0.775267 0.059 Uiso 1 1 calc R U . . .
C9 C 0.24372(18) 0.34146(15) 0.81665(12) 0.0417(3) Uani 1 1 d D . . . .
C10 C 0.1828(2) 0.18946(16) 0.76724(13) 0.0484(3) Uani 1 1 d . . . . .
H10 H 0.133984 0.115041 0.814634 0.058 Uiso 1 1 calc R U . . .
C11 C 0.1944(2) 0.14855(16) 0.64779(13) 0.0505(3) Uani 1 1 d . . . . .
H11 H 0.153695 0.04503 0.615813 0.061 Uiso 1 1 calc R U . . .
C12 C 0.23250(18) 0.55497(15) 1.10561(12) 0.0423(3) Uani 1 1 d D . . . .
C13 C 0.2865(2) 0.70647(16) 1.14985(13) 0.0502(3) Uani 1 1 d . . . . .
H13 H 0.343056 0.780085 1.104137 0.06 Uiso 1 1 calc R U . . .
C14 C 0.2568(2) 0.74865(16) 1.26136(14) 0.0521(3) Uani 1 1 d . . . . .
H14 H 0.295581 0.852464 1.290504 0.063 Uiso 1 1 calc R U . . .
C15 C 0.12226(19) 0.50368(16) 1.28731(13) 0.0472(3) Uani 1 1 d . . . . .
H15 H 0.064228 0.432609 1.334387 0.057 Uiso 1 1 calc R U . . .
C16 C 0.1479(2) 0.45103(16) 1.17645(13) 0.0471(3) Uani 1 1 d . . . . .
H16 H 0.108625 0.346698 1.149548 0.057 Uiso 1 1 calc DR U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3586(15) . ?
O1 H1 0.83 . ?
O2 C3 1.3557(16) . ?
O2 H2A 0.83 . ?
N1 C11 1.3334(19) . ?
N1 C7 1.3378(18) . ?
N2A N3A 1.231(8) . ?
N2A C9 1.482(11) . ?
N3A C12 1.491(12) . ?
C17 C18 1.312(7) . ?
C17 C9 1.441(11) . ?
C17 H17 0.94 . ?
C18 C12 1.436(11) . ?
C18 H18 0.94 . ?
N2B N3B 1.241(10) . ?
N2B C9 1.50(3) . ?
N3B C12 1.62(3) . ?
N4 C14 1.3335(19) . ?
N4 C15 1.3360(17) . ?
C1 C2 1.3857(17) . ?
C1 C6 1.3910(17) . ?
C2 C3 1.3910(18) . ?
C2 H2 0.94 . ?
C3 C4 1.3932(17) . ?
C4 C5 1.379(2) . ?
C4 H4 0.94 . ?
C5 C6 1.383(2) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3772(19) . ?
C7 H7 0.94 . ?
C8 C9 1.391(2) . ?
C8 H8 0.94 . ?
C9 C10 1.3840(18) . ?
C10 C11 1.3772(18) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.3797(19) . ?
C12 C16 1.3901(19) . ?
C13 C14 1.3737(19) . ?
C13 H13 0.94 . ?
C14 H14 0.94 . ?
C15 C16 1.3852(18) . ?
C15 H15 0.94 . ?
C16 H16 0.94 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 116.96(11) . . ?
N3A N2A C9 116.5(11) . . ?
N2A N3A C12 120.4(12) . . ?
C18 C17 C9 121.2(10) . . ?
C18 C17 H17 119.4 . . ?
C9 C17 H17 119.4 . . ?
C17 C18 C12 119.5(11) . . ?
C17 C18 H18 120.2 . . ?
C12 C18 H18 120.2 . . ?
N3B N2B C9 112(3) . . ?
N2B N3B C12 107(3) . . ?
C14 N4 C15 117.08(12) . . ?
O1 C1 C2 122.03(10) . . ?
O1 C1 C6 118.16(12) . . ?
C2 C1 C6 119.81(12) . . ?
C1 C2 C3 120.53(11) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O2 C3 C2 122.17(11) . . ?
O2 C3 C4 118.01(12) . . ?
C2 C3 C4 119.82(12) . . ?
C5 C4 C3 118.84(12) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.99(12) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.98(13) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.88(13) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.46(13) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C10 C9 C8 118.06(12) . . ?
C10 C9 C17 118.0(5) . . ?
C8 C9 C17 123.7(5) . . ?
C10 C9 N2A 116.1(5) . . ?
C8 C9 N2A 125.8(5) . . ?
C10 C9 N2B 150.8(11) . . ?
C8 C9 N2B 91.1(11) . . ?
C11 C10 C9 119.21(13) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C11 C10 123.39(13) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C13 C12 C16 117.80(12) . . ?
C13 C12 C18 115.4(6) . . ?
C16 C12 C18 126.8(6) . . ?
C13 C12 N3A 118.9(6) . . ?
C16 C12 N3A 123.3(6) . . ?
C13 C12 N3B 154.4(9) . . ?
C16 C12 N3B 87.7(9) . . ?
C14 C13 C12 119.33(13) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
N4 C14 C13 123.67(13) . . ?
N4 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
N4 C15 C16 123.18(13) . . ?
N4 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C15 C16 C12 118.93(13) . . ?
C15 C16 H16 120.5 . . ?
C12 C16 H16 120.5 . . ?

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
O1 H1 N1 0.83 1.93 2.7579(14) 176.1 . yes
O2 H2A N4 0.83 1.94 2.7734(14) 176.1 2_667 yes

####################################################################### 
# 
# 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_A50_BE50_210
_database_code_depnum_ccdc_archive 'CCDC 1995483'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT077_A50_BE50_210        
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)ethylene molecules within the structure.
;
# end Validation Reply Form

_audit_creation_date             2020-03-05T13:01:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C17.07 H15.07 N2.93 O2'
_chemical_formula_weight         293.25

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.01388(15)
_cell_length_b                   9.81882(18)
_cell_length_c                   10.87660(17)
_cell_angle_alpha                93.4063(14)
_cell_angle_beta                 106.7767(15)
_cell_angle_gamma                114.0626(18)
_cell_volume                     732.70(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    12908
_cell_measurement_theta_min      4.307
_cell_measurement_theta_max      76.96

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.102
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             308
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -1 1 0.0681
3 3 -3 0.0873
0 6 -2 0.0863
4 1 -1 0.0905
-1 -2 -4 0.0457
0 -6 2 0.0494
2 2 -7 0.0731
-1 0 7 0.036
-2 1 -5 0.0681
0 4 -6 0.0553
3 0 4 0.092
4 -5 -3 0.1384
-3 6 2 0.1189
1 -3 -5 0.0535
0 0 -7 0.0505
-3 6 -2 0.1171


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.501
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.929

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      210(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.1320262
_diffrn_orient_matrix_ub_12      -0.0772047
_diffrn_orient_matrix_ub_13      0.0519688
_diffrn_orient_matrix_ub_21      0.0247934
_diffrn_orient_matrix_ub_22      0.0590436
_diffrn_orient_matrix_ub_23      0.1416779
_diffrn_orient_matrix_ub_31      -0.1794373
_diffrn_orient_matrix_ub_32      -0.1460916
_diffrn_orient_matrix_ub_33      -0.0069622
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_number            22578
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.335
_diffrn_reflns_theta_max         77.356
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.957
_reflns_Friedel_coverage         0
_reflns_number_total             2977
_reflns_number_gt                2557
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0614P)²+0.0929P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0053(9)
_refine_ls_number_reflns         2977
_refine_ls_number_parameters     242
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1123
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)ethylene and the pedal motion about the azo group, the atom 
 sites N2 and N3, were split into parts A and B. These sites were allowed to 
 free refine their site occupancies to a total value of 1. To help maintain 
 reasonable ADP and bond lengths, SIMU, RIGU, and DFIX restraints and 
 constraints were applied. At this temperature the ratio of 4,4'-azopyridine 
 to bis(4-pyridyl)ethylene was 0.46 to 0.54 with the amount of 
 4,4'-azopyridine in the secondary position calculated at 0.03. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16498(12) 0.15949(10) 0.30907(8) 0.0458(2) Uani 1 1 d . . . . .
H1 H 0.196935 0.184864 0.389693 0.069 Uiso 1 1 calc R U . . .
O2 O 0.82376(13) 0.22637(12) 0.43308(9) 0.0526(3) Uani 1 1 d . . . . .
H2A H 0.828035 0.263982 0.504971 0.079 Uiso 1 1 calc R U . . .
N1 N 0.26076(16) 0.24838(13) 0.57526(10) 0.0463(3) Uani 1 1 d . . . . .
N2A N 0.218(3) 0.3773(13) 0.9433(13) 0.0385(18) Uani 0.437(3) 1 d D U P A 1
N3A N 0.267(2) 0.5130(13) 0.9847(11) 0.0405(18) Uani 0.437(3) 1 d D U P A 1
C17 C 0.215(3) 0.3788(13) 0.9353(13) 0.0393(16) Uani 0.536(3) 1 d D U P A 2
H17 H 0.158942 0.300212 0.977192 0.047 Uiso 0.536(3) 1 calc DR U P A 2
C18 C 0.2658(19) 0.5200(13) 0.9881(11) 0.0373(14) Uani 0.536(3) 1 d D U P A 2
H18 H 0.325011 0.599265 0.947728 0.045 Uiso 0.536(3) 1 calc R U P A 2
N2B N 0.272(6) 0.466(6) 0.921(4) 0.040(3) Uani 0.0264(18) 1 d D U P A 3
N3B N 0.191(6) 0.412(5) 1.000(4) 0.041(3) Uani 0.0264(18) 1 d D U P A 3
N4 N 0.17560(15) 0.65081(12) 1.33044(10) 0.0441(3) Uani 1 1 d . . . . .
C1 C 0.31670(18) 0.15523(13) 0.27965(11) 0.0377(3) Uani 1 1 d . . . . .
C2 C 0.49383(17) 0.19145(13) 0.37594(11) 0.0377(3) Uani 1 1 d . . . . .
H2 H 0.510449 0.218369 0.464563 0.045 Uiso 1 1 calc R U . . .
C3 C 0.64728(18) 0.18814(14) 0.34206(11) 0.0404(3) Uani 1 1 d . . . . .
C4 C 0.6214(2) 0.14486(14) 0.21086(12) 0.0456(3) Uani 1 1 d . . . . .
H4 H 0.723104 0.140255 0.187117 0.055 Uiso 1 1 calc R U . . .
C5 C 0.4443(2) 0.10896(14) 0.11657(12) 0.0471(3) Uani 1 1 d . . . . .
H5 H 0.427052 0.080764 0.028023 0.057 Uiso 1 1 calc R U . . .
C6 C 0.2909(2) 0.11319(14) 0.14843(11) 0.0445(3) Uani 1 1 d . . . . .
H6 H 0.171191 0.088078 0.082527 0.053 Uiso 1 1 calc R U . . .
C7 C 0.32273(19) 0.39558(15) 0.62494(13) 0.0470(3) Uani 1 1 d . . . . .
H7 H 0.371804 0.467775 0.575689 0.056 Uiso 1 1 calc R U . . .
C8 C 0.31864(19) 0.44723(15) 0.74429(12) 0.0445(3) Uani 1 1 d . . . . .
H8 H 0.365715 0.551902 0.775864 0.053 Uiso 1 1 calc R U . . .
C9 C 0.24335(17) 0.34105(14) 0.81684(11) 0.0381(3) Uani 1 1 d D . . . .
C10 C 0.18240(19) 0.18868(15) 0.76737(12) 0.0443(3) Uani 1 1 d . . . . .
H10 H 0.133563 0.114016 0.814753 0.053 Uiso 1 1 calc R U . . .
C11 C 0.19437(19) 0.14810(15) 0.64772(12) 0.0464(3) Uani 1 1 d . . . . .
H11 H 0.1537 0.04456 0.615606 0.056 Uiso 1 1 calc R U . . .
C12 C 0.23277(16) 0.55554(14) 1.10542(11) 0.0384(3) Uani 1 1 d D . . . .
C13 C 0.28691(19) 0.70727(15) 1.14967(12) 0.0457(3) Uani 1 1 d . . . . .
H13 H 0.343666 0.781072 1.103972 0.055 Uiso 1 1 calc R U . . .
C14 C 0.25687(19) 0.74942(15) 1.26161(13) 0.0477(3) Uani 1 1 d . . . . .
H14 H 0.295827 0.853292 1.290917 0.057 Uiso 1 1 calc R U . . .
C15 C 0.12178(18) 0.50349(15) 1.28708(12) 0.0433(3) Uani 1 1 d . . . . .
H15 H 0.063623 0.432205 1.334154 0.052 Uiso 1 1 calc R U . . .
C16 C 0.14762(18) 0.45103(15) 1.17625(12) 0.0430(3) Uani 1 1 d . . . . .
H16 H 0.108329 0.34663 1.149307 0.052 Uiso 1 1 calc DR U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3591(14) . ?
O1 H1 0.83 . ?
O2 C3 1.3549(15) . ?
O2 H2A 0.83 . ?
N1 C11 1.3345(18) . ?
N1 C7 1.3396(17) . ?
N2A N3A 1.236(7) . ?
N2A C9 1.492(11) . ?
N3A C12 1.488(10) . ?
C17 C18 1.315(7) . ?
C17 C9 1.423(11) . ?
C17 H17 0.94 . ?
C18 C12 1.427(11) . ?
C18 H18 0.94 . ?
N2B N3B 1.241(10) . ?
N2B C9 1.51(5) . ?
N3B C12 1.62(5) . ?
N4 C14 1.3325(18) . ?
N4 C15 1.3393(16) . ?
C1 C2 1.3872(16) . ?
C1 C6 1.3928(16) . ?
C2 C3 1.3935(17) . ?
C2 H2 0.94 . ?
C3 C4 1.3946(16) . ?
C4 C5 1.3781(19) . ?
C4 H4 0.94 . ?
C5 C6 1.3854(19) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3796(18) . ?
C7 H7 0.94 . ?
C8 C9 1.3904(18) . ?
C8 H8 0.94 . ?
C9 C10 1.3868(17) . ?
C10 C11 1.3796(17) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.3807(18) . ?
C12 C16 1.3923(18) . ?
C13 C14 1.3792(18) . ?
C13 H13 0.94 . ?
C14 H14 0.94 . ?
C15 C16 1.3852(17) . ?
C15 H15 0.94 . ?
C16 H16 0.94 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 117.11(11) . . ?
N3A N2A C9 116.3(10) . . ?
N2A N3A C12 119.0(10) . . ?
C18 C17 C9 122.2(10) . . ?
C18 C17 H17 118.9 . . ?
C9 C17 H17 118.9 . . ?
C17 C18 C12 121.5(10) . . ?
C17 C18 H18 119.3 . . ?
C12 C18 H18 119.3 . . ?
N3B N2B C9 111(4) . . ?
N2B N3B C12 106(4) . . ?
C14 N4 C15 117.20(11) . . ?
O1 C1 C2 121.92(10) . . ?
O1 C1 C6 118.17(11) . . ?
C2 C1 C6 119.91(11) . . ?
C1 C2 C3 120.38(10) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.05(10) . . ?
O2 C3 C4 118.11(11) . . ?
C2 C3 C4 119.84(11) . . ?
C5 C4 C3 118.95(12) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.94(11) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.96(12) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.73(12) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.54(12) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C10 C9 C8 118.11(11) . . ?
C10 C9 C17 118.0(5) . . ?
C8 C9 C17 123.7(5) . . ?
C10 C9 N2A 116.8(5) . . ?
C8 C9 N2A 125.1(5) . . ?
C10 C9 N2B 151.0(15) . . ?
C8 C9 N2B 90.9(15) . . ?
C11 C10 C9 119.14(12) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C11 C10 123.32(12) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C13 C12 C16 117.87(11) . . ?
C13 C12 C18 116.3(5) . . ?
C16 C12 C18 125.8(5) . . ?
C13 C12 N3A 118.3(5) . . ?
C16 C12 N3A 123.8(5) . . ?
C13 C12 N3B 154.4(13) . . ?
C16 C12 N3B 87.4(13) . . ?
C14 C13 C12 119.32(12) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
N4 C14 C13 123.52(12) . . ?
N4 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
N4 C15 C16 123.21(12) . . ?
N4 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C15 C16 C12 118.88(12) . . ?
C15 C16 H16 120.6 . . ?
C12 C16 H16 120.6 . . ?

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
O1 H1 N1 0.83 1.93 2.7575(13) 176.8 . yes
O2 H2A N4 0.83 1.94 2.7729(13) 177.2 2_667 yes

####################################################################### 
# 
# 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_A50_BE50_290
_database_code_depnum_ccdc_archive 'CCDC 1995487'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT077_A50_BE50_290        
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)ethylene molecules within the structure.
;
_vrf_PLAT230_A50_BE50_290        
;
PROBLEM: Hirshfeld Test Diff for    C12      --C16      .        6.2 s.u.  
RESPONSE: Due to the pedal motion of the 4,4'-azopyridine molecule.
;
# end Validation Reply Form

_audit_creation_date             2020-03-05T13:03:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C17.05 H15.05 N2.95 O2'
_chemical_formula_weight         293.27

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0886(2)
_cell_length_b                   9.8583(2)
_cell_length_c                   10.9012(2)
_cell_angle_alpha                93.7995(18)
_cell_angle_beta                 106.674(2)
_cell_angle_gamma                113.898(2)
_cell_volume                     744.61(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    9600
_cell_measurement_theta_min      4.296
_cell_measurement_theta_max      74.962

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.102
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             308
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -2 1 0.0681
3 3 -3 0.0873
0 6 -2 0.0863
4 1 -1 0.0905
-1 -2 -5 0.0457
0 -6 2 0.0494
2 2 -7 0.0731
-1 0 7 0.036
-2 1 -5 0.0681
0 3 -6 0.0553
3 0 4 0.092
4 -5 -3 0.1384
-3 6 2 0.1189
1 -3 -5 0.0535
0 0 -7 0.0505
-3 6 -2 0.1171


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.495
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.87
_shelx_estimated_absorpt_T_max   0.93

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      290(2)
_diffrn_ambient_environment      air
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.132173
_diffrn_orient_matrix_ub_12      -0.0749023
_diffrn_orient_matrix_ub_13      0.0543468
_diffrn_orient_matrix_ub_21      0.0198791
_diffrn_orient_matrix_ub_22      0.0590621
_diffrn_orient_matrix_ub_23      0.1404352
_diffrn_orient_matrix_ub_31      -0.1770728
_diffrn_orient_matrix_ub_32      -0.146433
_diffrn_orient_matrix_ub_33      -0.0086657
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_number            25036
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.329
_diffrn_reflns_theta_max         77.177
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.949
_reflns_Friedel_coverage         0
_reflns_number_total             3000
_reflns_number_gt                2311
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0598P)²+0.1023P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0052(9)
_refine_ls_number_reflns         3000
_refine_ls_number_parameters     242
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1288
_refine_ls_wR_factor_gt          0.1105
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.032

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)ethylene and the pedal motion about the azo group, the atom 
 sites N2 and N3, were split into parts A and B. These sites were allowed to 
 free refine their site occupancies to a total value of 1. To help maintain 
 reasonable ADP and bond lengths, SIMU, RIGU, and DFIX restraints and 
 constraints were applied. At this temperature the ratio of 4,4'-azopyridine 
 to bis(4-pyridyl)ethylene was 0.48 to 0.52 with the amount of 
 4,4'-azopyridine in the secondary position calculated at 0.11. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16665(16) 0.15562(14) 0.30938(10) 0.0669(3) Uani 1 1 d . . . . .
H1 H 0.19745 0.179655 0.389005 0.1 Uiso 1 1 calc R U . . .
O2 O 0.81952(17) 0.22494(16) 0.43217(11) 0.0774(4) Uani 1 1 d . . . . .
H2A H 0.823315 0.261231 0.503389 0.116 Uiso 1 1 calc R U . . .
N1 N 0.2599(2) 0.24740(17) 0.57523(13) 0.0652(4) Uani 1 1 d . . . . .
N2A N 0.226(3) 0.3797(19) 0.9437(15) 0.054(2) Uani 0.370(3) 1 d D U P A 1
N3A N 0.270(3) 0.512(2) 0.9887(17) 0.056(2) Uani 0.370(3) 1 d D U P A 1
C17 C 0.210(3) 0.3775(16) 0.9350(12) 0.0533(17) Uani 0.525(3) 1 d D U P A 2
H17 H 0.152388 0.300227 0.975383 0.064 Uiso 0.525(3) 1 calc DR U P A 2
C18 C 0.262(3) 0.5187(17) 0.9841(14) 0.0529(14) Uani 0.525(3) 1 d D U P A 2
H18 H 0.316118 0.59565 0.942571 0.064 Uiso 0.525(3) 1 calc R U P A 2
N2B N 0.275(2) 0.4694(19) 0.9244(13) 0.057(2) Uani 0.106(2) 1 d D U P A 3
N3B N 0.1921(19) 0.4055(16) 0.9984(13) 0.055(2) Uani 0.106(2) 1 d D U P A 3
N4 N 0.17733(18) 0.65036(16) 1.33035(12) 0.0614(3) Uani 1 1 d . . . . .
C1 C 0.3175(2) 0.15223(16) 0.27975(14) 0.0529(3) Uani 1 1 d . . . . .
C2 C 0.4927(2) 0.18871(16) 0.37545(13) 0.0543(4) Uani 1 1 d . . . . .
H2 H 0.508885 0.21487 0.463097 0.065 Uiso 1 1 calc R U . . .
C3 C 0.6446(2) 0.18650(17) 0.34141(14) 0.0573(4) Uani 1 1 d . . . . .
C4 C 0.6192(3) 0.14410(19) 0.21071(16) 0.0649(4) Uani 1 1 d . . . . .
H4 H 0.719036 0.14015 0.186944 0.078 Uiso 1 1 calc R U . . .
C5 C 0.4439(3) 0.10806(19) 0.11707(15) 0.0678(5) Uani 1 1 d . . . . .
H5 H 0.427057 0.080645 0.029467 0.081 Uiso 1 1 calc R U . . .
C6 C 0.2924(3) 0.11134(18) 0.14912(15) 0.0628(4) Uani 1 1 d . . . . .
H6 H 0.175177 0.086488 0.084097 0.075 Uiso 1 1 calc R U . . .
C7 C 0.3221(2) 0.3943(2) 0.62403(17) 0.0673(4) Uani 1 1 d . . . . .
H7 H 0.369963 0.464431 0.574963 0.081 Uiso 1 1 calc R U . . .
C8 C 0.3190(2) 0.4473(2) 0.74307(16) 0.0649(4) Uani 1 1 d . . . . .
H8 H 0.365928 0.550775 0.773987 0.078 Uiso 1 1 calc R U . . .
C9 C 0.2449(2) 0.34386(19) 0.81569(14) 0.0567(4) Uani 1 1 d D . . . .
C10 C 0.1841(2) 0.19290(19) 0.76702(16) 0.0640(4) Uani 1 1 d . . . . .
H10 H 0.136219 0.120377 0.814242 0.077 Uiso 1 1 calc R U . . .
C11 C 0.1946(2) 0.1502(2) 0.64847(16) 0.0657(4) Uani 1 1 d . . . . .
H11 H 0.153745 0.047723 0.617469 0.079 Uiso 1 1 calc R U . . .
C12 C 0.2312(2) 0.5528(2) 1.10606(14) 0.0584(4) Uani 1 1 d D . . . .
C13 C 0.2850(3) 0.7023(2) 1.14968(16) 0.0673(4) Uani 1 1 d . . . . .
H13 H 0.340231 0.774166 1.104161 0.081 Uiso 1 1 calc R U . . .
C14 C 0.2573(3) 0.7459(2) 1.26087(17) 0.0685(4) Uani 1 1 d . . . . .
H14 H 0.296753 0.848717 1.289511 0.082 Uiso 1 1 calc R U . . .
C15 C 0.1229(2) 0.5038(2) 1.28790(15) 0.0625(4) Uani 1 1 d . . . . .
H15 H 0.065774 0.434589 1.33468 0.075 Uiso 1 1 calc R U . . .
C16 C 0.1476(2) 0.44986(19) 1.17684(16) 0.0636(4) Uani 1 1 d . . . . .
H16 H 0.108874 0.346817 1.150359 0.076 Uiso 1 1 calc DR U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3606(18) . ?
O1 H1 0.82 . ?
O2 C3 1.3554(19) . ?
O2 H2A 0.82 . ?
N1 C11 1.330(2) . ?
N1 C7 1.337(2) . ?
N2A N3A 1.228(8) . ?
N2A C9 1.483(13) . ?
N3A C12 1.471(14) . ?
C17 C18 1.304(7) . ?
C17 C9 1.453(11) . ?
C17 H17 0.93 . ?
C18 C12 1.461(11) . ?
C18 H18 0.93 . ?
N2B N3B 1.237(10) . ?
N2B C9 1.547(16) . ?
N3B C12 1.665(15) . ?
N4 C14 1.327(2) . ?
N4 C15 1.332(2) . ?
C1 C2 1.384(2) . ?
C1 C6 1.387(2) . ?
C2 C3 1.389(2) . ?
C2 H2 0.93 . ?
C3 C4 1.389(2) . ?
C4 C5 1.375(2) . ?
C4 H4 0.93 . ?
C5 C6 1.379(2) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.377(2) . ?
C7 H7 0.93 . ?
C8 C9 1.382(2) . ?
C8 H8 0.93 . ?
C9 C10 1.375(2) . ?
C10 C11 1.369(2) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 C13 1.363(2) . ?
C12 C16 1.389(2) . ?
C13 C14 1.367(2) . ?
C13 H13 0.93 . ?
C14 H14 0.93 . ?
C15 C16 1.389(2) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 116.76(14) . . ?
N3A N2A C9 118.4(13) . . ?
N2A N3A C12 121.1(14) . . ?
C18 C17 C9 118.3(11) . . ?
C18 C17 H17 120.8 . . ?
C9 C17 H17 120.8 . . ?
C17 C18 C12 118.3(12) . . ?
C17 C18 H18 120.9 . . ?
C12 C18 H18 120.9 . . ?
N3B N2B C9 107.2(15) . . ?
N2B N3B C12 101.7(13) . . ?
C14 N4 C15 116.99(14) . . ?
O1 C1 C2 122.00(12) . . ?
O1 C1 C6 118.17(14) . . ?
C2 C1 C6 119.84(14) . . ?
C1 C2 C3 120.42(13) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.06(13) . . ?
O2 C3 C4 118.12(14) . . ?
C2 C3 C4 119.82(15) . . ?
C5 C4 C3 118.87(15) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.01(14) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.03(15) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.51(16) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 118.71(16) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C8 117.96(14) . . ?
C10 C9 C17 115.7(6) . . ?
C8 C9 C17 126.1(6) . . ?
C10 C9 N2A 115.9(7) . . ?
C8 C9 N2A 126.2(7) . . ?
C10 C9 N2B 149.5(5) . . ?
C8 C9 N2B 92.5(5) . . ?
C11 C10 C9 119.45(16) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
N1 C11 C10 123.56(16) . . ?
N1 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
C13 C12 C16 117.96(15) . . ?
C13 C12 C18 114.8(6) . . ?
C16 C12 C18 127.2(7) . . ?
C13 C12 N3A 117.5(7) . . ?
C16 C12 N3A 124.5(7) . . ?
C13 C12 N3B 154.0(4) . . ?
C16 C12 N3B 87.8(4) . . ?
C12 C13 C14 119.51(16) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
N4 C14 C13 123.92(16) . . ?
N4 C14 H14 118 . . ?
C13 C14 H14 118 . . ?
N4 C15 C16 122.87(16) . . ?
N4 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C15 C16 C12 118.72(16) . . ?
C15 C16 H16 120.6 . . ?
C12 C16 H16 120.6 . . ?

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
O1 H1 N1 0.82 1.94 2.7625(17) 175.3 . yes
O2 H2A N4 0.82 1.96 2.7801(16) 177.5 2_667 yes

####################################################################### 
# 
# 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_A75_BE25_230
_database_code_depnum_ccdc_archive 'CCDC 1995490'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT077_A75_BE25_230        
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)ethylene molecules within the structure. 
;
# end Validation Reply Form

_audit_creation_date             2020-03-12T16:24:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C16.46 H14.46 N3.54 O2'
_chemical_formula_weight         293.85

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.98898(12)
_cell_length_b                   9.77584(13)
_cell_length_c                   10.85419(16)
_cell_angle_alpha                93.7189(12)
_cell_angle_beta                 106.5072(14)
_cell_angle_gamma                113.8224(14)
_cell_volume                     727.76(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    14193
_cell_measurement_theta_min      4.309
_cell_measurement_theta_max      76.396

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.056
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             308
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 6 -1 0.055
0 4 4 0.0525
0 -6 2 0.0757
3 -6 0 0.0674
5 -1 0 0.0887
5 0 -3 0.0947
0 0 7 0.026
0 0 -7 0.0283
-2 -3 -2 0.0761
-5 0 3 0.0919


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.659
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.854
_shelx_estimated_absorpt_T_max   0.959

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      230(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0288157
_diffrn_orient_matrix_ub_12      -0.16591
_diffrn_orient_matrix_ub_13      -0.0025372
_diffrn_orient_matrix_ub_21      -0.1022232
_diffrn_orient_matrix_ub_22      -0.0392667
_diffrn_orient_matrix_ub_23      -0.1499376
_diffrn_orient_matrix_ub_31      0.1973851
_diffrn_orient_matrix_ub_32      0.0436631
_diffrn_orient_matrix_ub_33      -0.019637
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_number            27433
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.34
_diffrn_reflns_theta_max         77.316
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_reflns_Friedel_coverage         0
_reflns_number_total             2997
_reflns_number_gt                2686
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0654P)²+0.0841P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0049(10)
_refine_ls_number_reflns         2997
_refine_ls_number_parameters     242
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1168
_refine_ls_wR_factor_gt          0.1134
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)ethylene and the pedal motion about the azo group, the atom 
 sites N2 and N3, were split into parts A and B. These sites were allowed to 
 free refine their site occupancies to a total value of 1. To help maintain 
 reasonable ADP and bond lengths, SIMU, RIGU, and DFIX restraints and 
 constraints were applied. At this temperature the ratio of 4,4'-azopyridine 
 to bis(4-pyridyl)ethylene was 0.77 to 0.23 with the amount of 
 4,4'-azopyridine in the secondary position calculated at 0.05. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16517(12) 0.16059(10) 0.31159(8) 0.0487(2) Uani 1 1 d . . . . .
H1 H 0.197061 0.185901 0.392371 0.073 Uiso 1 1 calc R U . . .
O2 O 0.82309(13) 0.22373(11) 0.43419(9) 0.0568(3) Uani 1 1 d . . . . .
H2A H 0.82749 0.261963 0.50627 0.085 Uiso 1 1 calc R U . . .
N1 N 0.26054(15) 0.24909(12) 0.57922(10) 0.0485(3) Uani 1 1 d . . . . .
N2A N 0.2131(16) 0.3753(7) 0.9434(7) 0.0420(8) Uani 0.723(3) 1 d D U P A 1
N3A N 0.2686(10) 0.5138(6) 0.9819(4) 0.0410(6) Uani 0.723(3) 1 d D U P A 1
C17 C 0.214(6) 0.384(3) 0.937(3) 0.043(2) Uani 0.230(3) 1 d D U P A 2
H17 H 0.154695 0.303624 0.976564 0.052 Uiso 0.230(3) 1 calc R U P A 2
C18 C 0.260(4) 0.523(2) 0.9975(14) 0.0390(19) Uani 0.230(3) 1 d D U P A 2
H18 H 0.317247 0.604971 0.959234 0.047 Uiso 0.230(3) 1 calc DR U P A 2
N2B N 0.281(3) 0.473(3) 0.929(2) 0.045(3) Uani 0.047(2) 1 d D U P A 3
N3B N 0.190(3) 0.402(3) 0.997(2) 0.047(3) Uani 0.047(2) 1 d D U P A 3
N4 N 0.17589(14) 0.65020(12) 1.32797(9) 0.0464(3) Uani 1 1 d . . . . .
C1 C 0.31701(17) 0.15595(12) 0.28146(11) 0.0399(3) Uani 1 1 d . . . . .
C2 C 0.49342(17) 0.19032(12) 0.37765(10) 0.0411(3) Uani 1 1 d . . . . .
H2 H 0.509412 0.216248 0.466548 0.049 Uiso 1 1 calc R U . . .
C3 C 0.64697(18) 0.18662(13) 0.34321(11) 0.0433(3) Uani 1 1 d . . . . .
C4 C 0.6220(2) 0.14439(14) 0.21174(12) 0.0485(3) Uani 1 1 d . . . . .
H4 H 0.723642 0.139186 0.187582 0.058 Uiso 1 1 calc R U . . .
C5 C 0.4451(2) 0.11032(14) 0.11760(11) 0.0501(3) Uani 1 1 d . . . . .
H5 H 0.428323 0.082819 0.028767 0.06 Uiso 1 1 calc R U . . .
C6 C 0.29174(19) 0.11537(13) 0.14988(11) 0.0474(3) Uani 1 1 d . . . . .
H6 H 0.172682 0.091811 0.084068 0.057 Uiso 1 1 calc R U . . .
C7 C 0.32342(19) 0.39702(14) 0.62926(12) 0.0503(3) Uani 1 1 d . . . . .
H7 H 0.373193 0.469169 0.580068 0.06 Uiso 1 1 calc R U . . .
C8 C 0.31921(18) 0.44936(14) 0.74895(12) 0.0476(3) Uani 1 1 d . . . . .
H8 H 0.366886 0.55441 0.781121 0.057 Uiso 1 1 calc DR U . . .
C9 C 0.24258(16) 0.34258(13) 0.82061(11) 0.0417(3) Uani 1 1 d D . . . .
C10 C 0.18054(18) 0.18962(14) 0.77109(12) 0.0471(3) Uani 1 1 d . . . . .
H10 H 0.130914 0.114982 0.818383 0.057 Uiso 1 1 calc R U . . .
C11 C 0.19281(18) 0.14871(14) 0.65123(12) 0.0489(3) Uani 1 1 d . . . . .
H11 H 0.151295 0.044701 0.61856 0.059 Uiso 1 1 calc R U . . .
C12 C 0.23182(16) 0.55271(14) 1.10308(11) 0.0422(3) Uani 1 1 d D . . . .
C13 C 0.28739(19) 0.70491(14) 1.14686(12) 0.0495(3) Uani 1 1 d . . . . .
H13 H 0.344933 0.778213 1.100945 0.059 Uiso 1 1 calc R U . . .
C14 C 0.25758(19) 0.74836(14) 1.25877(13) 0.0507(3) Uani 1 1 d . . . . .
H14 H 0.296882 0.85277 1.287999 0.061 Uiso 1 1 calc R U . . .
C15 C 0.12096(18) 0.50194(14) 1.28495(12) 0.0465(3) Uani 1 1 d . . . . .
H15 H 0.06269 0.431246 1.332499 0.056 Uiso 1 1 calc R U . . .
C16 C 0.14600(18) 0.44789(14) 1.17368(12) 0.0465(3) Uani 1 1 d . . . . .
H16 H 0.106041 0.342988 1.146443 0.056 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3595(14) . ?
O1 H1 0.83 . ?
O2 C3 1.3558(15) . ?
O2 H2A 0.83 . ?
N1 C11 1.3333(17) . ?
N1 C7 1.3397(16) . ?
N2A N3A 1.241(4) . ?
N2A C9 1.455(5) . ?
N3A C12 1.485(3) . ?
C17 C18 1.320(10) . ?
C17 C9 1.412(19) . ?
C17 H17 0.94 . ?
C18 C12 1.266(9) . ?
C18 H18 0.94 . ?
N2B N3B 1.243(10) . ?
N2B C9 1.54(3) . ?
N3B C12 1.67(3) . ?
N4 C14 1.3331(17) . ?
N4 C15 1.3391(16) . ?
C1 C2 1.3874(16) . ?
C1 C6 1.3914(15) . ?
C2 C3 1.3931(17) . ?
C2 H2 0.94 . ?
C3 C4 1.3934(16) . ?
C4 C5 1.3807(19) . ?
C4 H4 0.94 . ?
C5 C6 1.3847(18) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3796(17) . ?
C7 H7 0.94 . ?
C8 C9 1.3889(17) . ?
C8 H8 0.94 . ?
C9 C10 1.3843(16) . ?
C10 C11 1.3779(17) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.3753(17) . ?
C12 C16 1.3929(17) . ?
C13 C14 1.3754(18) . ?
C13 H13 0.94 . ?
C14 H14 0.94 . ?
C15 C16 1.3848(17) . ?
C15 H15 0.94 . ?
C16 H16 0.94 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 117.26(10) . . ?
N3A N2A C9 112.5(5) . . ?
N2A N3A C12 114.7(4) . . ?
C18 C17 C9 127.8(19) . . ?
C18 C17 H17 116.1 . . ?
C9 C17 H17 116.1 . . ?
C12 C18 C17 124.7(16) . . ?
C12 C18 H18 117.6 . . ?
C17 C18 H18 117.6 . . ?
N3B N2B C9 102(2) . . ?
N2B N3B C12 97(2) . . ?
C14 N4 C15 117.45(10) . . ?
O1 C1 C2 121.85(9) . . ?
O1 C1 C6 118.13(11) . . ?
C2 C1 C6 120.02(11) . . ?
C1 C2 C3 120.36(10) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.00(10) . . ?
O2 C3 C4 118.09(11) . . ?
C2 C3 C4 119.91(11) . . ?
C5 C4 C3 118.78(11) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.10(10) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.81(11) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C8 123.66(11) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 118.18(11) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C10 C9 C8 118.68(11) . . ?
C10 C9 C17 119.1(10) . . ?
C8 C9 C17 122.0(10) . . ?
C10 C9 N2A 115.4(3) . . ?
C8 C9 N2A 125.9(3) . . ?
C10 C9 N2B 151.6(8) . . ?
C8 C9 N2B 89.6(8) . . ?
C11 C10 C9 118.82(11) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.36(11) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C18 C12 C13 114.8(10) . . ?
C18 C12 C16 126.6(10) . . ?
C13 C12 C16 118.55(11) . . ?
C13 C12 N3A 116.3(2) . . ?
C16 C12 N3A 125.2(2) . . ?
C13 C12 N3B 155.2(7) . . ?
C16 C12 N3B 86.0(7) . . ?
C12 C13 C14 119.07(11) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
N4 C14 C13 123.46(11) . . ?
N4 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
N4 C15 C16 123.07(11) . . ?
N4 C15 H15 118.5 . . ?
C16 C15 H15 118.5 . . ?
C15 C16 C12 118.41(11) . . ?
C15 C16 H16 120.8 . . ?
C12 C16 H16 120.8 . . ?

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
O1 H1 N1 0.83 1.94 2.7661(13) 176.8 . yes
O2 H2A N4 0.83 1.95 2.7840(13) 177.1 2_667 yes

####################################################################### 
# 
# 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_A25_BA75_250
_database_code_depnum_ccdc_archive 'CCDC 1995553'
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;


# start Validation Reply Form
_vrf_PLAT077_A25_BA75_250        
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)acetylene molecules.
;
_vrf_PLAT911_A25_BA75_250        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         26 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2020-02-26T14:19:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C17.34 H14 N2.66 O2'
_chemical_formula_weight         291.64

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.17264(14)
_cell_length_b                   9.78791(16)
_cell_length_c                   10.94559(17)
_cell_angle_alpha                92.4657(13)
_cell_angle_beta                 107.8278(15)
_cell_angle_gamma                114.4086(16)
_cell_volume                     744.37(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    14025
_cell_measurement_theta_min      4.316
_cell_measurement_theta_max      76.968

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.103
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             305
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -1 0 0.0411
-3 5 4 0.0981
-1 -3 7 0.0767
1 3 -7 0.0786
2 -1 -7 0.0773
4 1 0 0.0599
2 -6 2 0.0625
0 -5 -2 0.0599
4 -1 -6 0.0847
3 -4 4 0.0491
-5 2 4 0.0882
1 -6 -1 0.0572
0 6 -2 0.0472
-2 6 -2 0.0453
1 -5 5 0.0477


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.575
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.871
_shelx_estimated_absorpt_T_max   0.931

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      250(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.1808945
_diffrn_orient_matrix_ub_12      -0.1491905
_diffrn_orient_matrix_ub_13      -0.0767313
_diffrn_orient_matrix_ub_21      -0.1278282
_diffrn_orient_matrix_ub_22      0.0727983
_diffrn_orient_matrix_ub_23      0.018582
_diffrn_orient_matrix_ub_31      -0.003006
_diffrn_orient_matrix_ub_32      0.0592056
_diffrn_orient_matrix_ub_33      -0.1284327
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_number            23815
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.326
_diffrn_reflns_theta_max         77.156
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.99
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.99
_diffrn_reflns_point_group_measured_fraction_max 0.942
_reflns_Friedel_coverage         0
_reflns_number_total             2977
_reflns_number_gt                2485
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0623P)²+0.0679P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0048(10)
_refine_ls_number_reflns         2977
_refine_ls_number_parameters     284
_refine_ls_number_restraints     519
_refine_ls_R_factor_all          0.047
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.033

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)acetylene and the pedal motion about the azo group and pyridyl
 rings, the atom sites N2 < N4 and C12 < C16, were split into parts A and B.
 These sites were allowed to free refine their site occupancies to a total 
 value of 1. To help maintain reasonable ADP and bond lengths, SIMU, RIGU, and 
 DFIX restraints and constraints were applied. At this temperature the ratio of 
 4,4'-azopyridine to bis(4-pyridyl)acetylene was 0.30 to 0.67 with the amount 
 of 4,4'-azopyridine in the secondary position calculated at 0.03. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16839(12) 0.14739(11) 0.30714(9) 0.0604(3) Uani 1 1 d . . . . .
H1 H 0.201296 0.173074 0.387462 0.091 Uiso 1 1 calc R U . . .
O2 O 0.81609(14) 0.21160(12) 0.43387(10) 0.0697(3) Uani 1 1 d . . . . .
H2A H 0.823549 0.251891 0.50493 0.105 Uiso 1 1 calc R U . . .
N1 N 0.26243(15) 0.24291(13) -0.42944(11) 0.0614(3) Uani 1 1 d . . . . .
C1 C 0.31837(18) 0.14710(12) 0.27839(12) 0.0499(3) Uani 1 1 d . . . . .
C2 C 0.49169(17) 0.17811(13) 0.37518(12) 0.0501(3) Uani 1 1 d . . . . .
H2 H 0.507148 0.199355 0.463685 0.06 Uiso 1 1 calc R U . . .
C3 C 0.64301(18) 0.17799(14) 0.34210(13) 0.0542(3) Uani 1 1 d . . . . .
C4 C 0.6188(2) 0.14297(15) 0.21153(14) 0.0628(4) Uani 1 1 d . . . . .
H4 H 0.719071 0.140099 0.188241 0.075 Uiso 1 1 calc R U . . .
C5 C 0.4453(2) 0.11248(16) 0.11663(13) 0.0662(4) Uani 1 1 d . . . . .
H5 H 0.429097 0.089462 0.02817 0.079 Uiso 1 1 calc R U . . .
C6 C 0.2950(2) 0.11470(15) 0.14744(13) 0.0604(3) Uani 1 1 d . . . . .
H6 H 0.178422 0.094633 0.080997 0.072 Uiso 1 1 calc R U . . .
C7 C 0.3293(2) 0.39231(17) -0.38637(15) 0.0645(4) Uani 1 1 d . . . . .
H7 H 0.377218 0.460444 -0.438874 0.077 Uiso 1 1 calc R U . . .
C8 C 0.33176(19) 0.45181(15) -0.26970(15) 0.0616(3) Uani 1 1 d . . . . .
H8 H 0.382608 0.558076 -0.242465 0.074 Uiso 1 1 calc R U . . .
C9 C 0.25783(17) 0.35219(14) -0.19275(12) 0.0524(3) Uani 1 1 d D . . . .
C10 C 0.18984(18) 0.19628(14) -0.23570(13) 0.0558(3) Uani 1 1 d . . . . .
H10 H 0.140587 0.125366 -0.185466 0.067 Uiso 1 1 calc R U . . .
C11 C 0.19634(19) 0.14828(15) -0.35331(13) 0.0591(3) Uani 1 1 d . . . . .
H11 H 0.151716 0.042971 -0.381468 0.071 Uiso 1 1 calc R U . . .
N2A N 0.2212(17) 0.3819(11) -0.0636(12) 0.0537(19) Uani 0.298(3) 1 d D U P A 1
N3A N 0.2598(10) 0.5053(8) -0.0135(8) 0.0606(15) Uani 0.298(3) 1 d D U P A 1
C12A C 0.229(2) 0.5538(13) 0.1044(11) 0.0479(15) Uani 0.298(3) 1 d . U P A 1
C13A C 0.280(2) 0.7045(13) 0.1561(12) 0.0565(18) Uani 0.298(3) 1 d . U P A 1
H13A H 0.336236 0.786338 0.116837 0.068 Uiso 0.298(3) 1 calc R U P A 1
C14A C 0.242(2) 0.7264(10) 0.2690(12) 0.0525(16) Uani 0.298(3) 1 d . U P A 1
H14A H 0.279397 0.82899 0.302636 0.063 Uiso 0.298(3) 1 calc R U P A 1
N4A N 0.171(2) 0.6381(12) 0.3300(11) 0.0586(19) Uani 0.298(3) 1 d . U P A 1
C15A C 0.1224(16) 0.5056(11) 0.2798(10) 0.0545(17) Uani 0.298(3) 1 d . U P A 1
H15A H 0.059658 0.430112 0.322005 0.065 Uiso 0.298(3) 1 calc R U P A 1
C16A C 0.1457(16) 0.4514(10) 0.1708(9) 0.0545(19) Uani 0.298(3) 1 d . U P A 1
H16A H 0.104335 0.346309 0.144067 0.065 Uiso 0.298(3) 1 calc R U P A 1
C12B C 0.2117(7) 0.5255(4) 0.1245(4) 0.0460(10) Uani 0.702(3) 1 d DG U P A 2
C13B C 0.2796(8) 0.6833(4) 0.1497(4) 0.0546(10) Uani 0.702(3) 1 d G U P A 2
H13B H 0.338587 0.742629 0.096121 0.066 Uiso 0.702(3) 1 calc R U P A 2
C14B C 0.2604(8) 0.7535(3) 0.2540(5) 0.0537(9) Uani 0.702(3) 1 d G U P A 2
H14B H 0.306289 0.860223 0.270988 0.064 Uiso 0.702(3) 1 calc R U P A 2
N4B N 0.1732(8) 0.6658(4) 0.3332(4) 0.0538(8) Uani 0.702(3) 1 d G U P A 2
C15B C 0.1053(7) 0.5079(4) 0.3080(3) 0.0545(8) Uani 0.702(3) 1 d G U P A 2
H15B H 0.046332 0.448618 0.361563 0.065 Uiso 0.702(3) 1 calc R U P A 2
C16B C 0.1246(6) 0.4378(3) 0.2037(3) 0.0505(8) Uani 0.702(3) 1 d G U P A 2
H16B H 0.078629 0.331021 0.186696 0.061 Uiso 0.702(3) 1 calc R U P A 2
C17 C 0.2322(6) 0.4598(5) 0.0166(3) 0.0490(7) Uani 0.668(3) 1 d D U P A 2
C18 C 0.2531(9) 0.4152(7) -0.0793(6) 0.0519(11) Uani 0.668(3) 1 d D U P A 2
N2B N 0.288(7) 0.476(6) -0.071(6) 0.056(4) Uani 0.034(3) 1 d D U P A 3
N3B N 0.171(6) 0.390(6) -0.024(5) 0.057(5) Uani 0.034(3) 1 d D U P A 3



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3566(15) . ?
O1 H1 0.83 . ?
O2 C3 1.3546(16) . ?
O2 H2A 0.83 . ?
N1 C11 1.3313(18) . ?
N1 C7 1.3348(18) . ?
C1 C2 1.3853(17) . ?
C1 C6 1.3908(18) . ?
C2 C3 1.3914(17) . ?
C2 H2 0.94 . ?
C3 C4 1.3884(18) . ?
C4 C5 1.378(2) . ?
C4 H4 0.94 . ?
C5 C6 1.378(2) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.371(2) . ?
C7 H7 0.94 . ?
C8 C9 1.386(2) . ?
C8 H8 0.94 . ?
C9 C18 1.381(6) . ?
C9 C10 1.3914(17) . ?
C9 N2A 1.571(12) . ?
C9 N2B 1.65(7) . ?
C10 C11 1.3751(18) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
N2A N3A 1.176(13) . ?
N3A C12A 1.482(13) . ?
C12A C16A 1.342(10) . ?
C12A C13A 1.395(9) . ?
C13A C14A 1.391(10) . ?
C13A H13A 0.94 . ?
C14A N4A 1.184(10) . ?
C14A C15A 1.997(11) . ?
C14A H14A 0.94 . ?
N4A C15A 1.232(9) . ?
C15A C16A 1.382(10) . ?
C15A H15A 0.94 . ?
C16A H16A 0.94 . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
C12B C17 1.408(4) . ?
C13B C14B 1.39 . ?
C13B H13B 0.94 . ?
C14B N4B 1.39 . ?
C14B H14B 0.94 . ?
N4B C15B 1.39 . ?
C15B C16B 1.39 . ?
C15B H15B 0.94 . ?
C16B H16B 0.94 . ?
C17 C18 1.205(7) . ?
N2B N3B 1.25(2) . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 117.34(12) . . ?
O1 C1 C2 121.90(11) . . ?
O1 C1 C6 118.24(12) . . ?
C2 C1 C6 119.87(12) . . ?
C1 C2 C3 120.35(12) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C4 118.11(12) . . ?
O2 C3 C2 122.02(11) . . ?
C4 C3 C2 119.87(12) . . ?
C5 C4 C3 118.91(13) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 122.02(12) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.96(13) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.58(13) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 118.69(12) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C18 C9 C8 117.2(2) . . ?
C18 C9 C10 124.4(2) . . ?
C8 C9 C10 118.32(12) . . ?
C8 C9 N2A 131.0(4) . . ?
C10 C9 N2A 110.6(4) . . ?
C8 C9 N2B 99.9(14) . . ?
C10 C9 N2B 141.8(14) . . ?
C11 C10 C9 118.49(12) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
N1 C11 C10 123.54(12) . . ?
N1 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
N3A N2A C9 121.9(11) . . ?
N2A N3A C12A 129.3(12) . . ?
C16A C12A C13A 113.9(6) . . ?
C16A C12A N3A 121.2(8) . . ?
C13A C12A N3A 124.9(9) . . ?
C14A C13A C12A 116.0(7) . . ?
C14A C13A H13A 122 . . ?
C12A C13A H13A 122 . . ?
N4A C14A C13A 131.1(7) . . ?
N4A C14A C15A 35.1(4) . . ?
C13A C14A C15A 96.0(5) . . ?
N4A C14A H14A 114.5 . . ?
C13A C14A H14A 114.5 . . ?
C15A C14A H14A 149.5 . . ?
C14A N4A C15A 111.5(6) . . ?
N4A C15A C16A 129.7(7) . . ?
N4A C15A C14A 33.5(3) . . ?
C16A C15A C14A 96.3(5) . . ?
N4A C15A H15A 115.1 . . ?
C16A C15A H15A 115.1 . . ?
C14A C15A H15A 148.5 . . ?
C12A C16A C15A 117.7(6) . . ?
C12A C16A H16A 121.1 . . ?
C15A C16A H16A 121.1 . . ?
C13B C12B C16B 120 . . ?
C13B C12B C17 117.8(3) . . ?
C16B C12B C17 122.2(3) . . ?
C12B C13B C14B 120 . . ?
C12B C13B H13B 120 . . ?
C14B C13B H13B 120 . . ?
N4B C14B C13B 120 . . ?
N4B C14B H14B 120 . . ?
C13B C14B H14B 120 . . ?
C14B N4B C15B 120 . . ?
C16B C15B N4B 120 . . ?
C16B C15B H15B 120 . . ?
N4B C15B H15B 120 . . ?
C15B C16B C12B 120 . . ?
C15B C16B H16B 120 . . ?
C12B C16B H16B 120 . . ?
C18 C17 C12B 174.4(5) . . ?
C17 C18 C9 174.1(6) . . ?
N3B N2B C9 100(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
O1 C1 C2 C3 -179.50(10) . . . . ?
C6 C1 C2 C3 0.41(18) . . . . ?
C1 C2 C3 O2 178.28(11) . . . . ?
C1 C2 C3 C4 -1.57(18) . . . . ?
O2 C3 C4 C5 -178.28(12) . . . . ?
C2 C3 C4 C5 1.57(19) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
O1 C1 C6 C5 -179.37(11) . . . . ?
C2 C1 C6 C5 0.72(19) . . . . ?
C11 N1 C7 C8 -0.5(2) . . . . ?
N1 C7 C8 C9 -1.3(2) . . . . ?
C7 C8 C9 C18 -176.6(4) . . . . ?
C7 C8 C9 C10 1.98(19) . . . . ?
C7 C8 C9 N2A -173.1(6) . . . . ?
C7 C8 C9 N2B -178.6(19) . . . . ?
C18 C9 C10 C11 177.5(4) . . . . ?
C8 C9 C10 C11 -1.03(18) . . . . ?
N2A C9 C10 C11 175.0(5) . . . . ?
N2B C9 C10 C11 180(3) . . . . ?
C7 N1 C11 C10 1.50(19) . . . . ?
C9 C10 C11 N1 -0.8(2) . . . . ?
C8 C9 N2A N3A -1.2(16) . . . . ?
C10 C9 N2A N3A -176.6(10) . . . . ?
C9 N2A N3A C12A 177.6(9) . . . . ?
N2A N3A C12A C16A -0.5(18) . . . . ?
N2A N3A C12A C13A -179.7(12) . . . . ?
C16A C12A C13A C14A 1.9(8) . . . . ?
N3A C12A C13A C14A -178.9(12) . . . . ?
C12A C13A C14A N4A -0.9(10) . . . . ?
C12A C13A C14A C15A -1.7(6) . . . . ?
C13A C14A N4A C15A -1.4(9) . . . . ?
C14A N4A C15A C16A 2.9(9) . . . . ?
C13A C12A C16A C15A -0.7(8) . . . . ?
N3A C12A C16A C15A 180.0(11) . . . . ?
N4A C15A C16A C12A -1.9(10) . . . . ?
C14A C15A C16A C12A -0.3(6) . . . . ?
C16B C12B C13B C14B 0 . . . . ?
C17 C12B C13B C14B 179.1(5) . . . . ?
C12B C13B C14B N4B 0 . . . . ?
C13B C14B N4B C15B 0 . . . . ?
C14B N4B C15B C16B 0 . . . . ?
N4B C15B C16B C12B 0 . . . . ?
C13B C12B C16B C15B 0 . . . . ?
C17 C12B C16B C15B -179.1(5) . . . . ?
C8 C9 N2B N3B 160(4) . . . . ?
C10 C9 N2B N3B -21(6) . . . . ?

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
O1 H1 N1 0.83 1.93 2.7561(14) 174.5 1_556 yes
O2 H2A N4A 0.83 2.04 2.871(9) 174.5 2_666 yes
O2 H2A N4B 0.83 1.9 2.73(2) 176.6 2_666 yes
####################################################################### 
# 
# 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_A25_BA75_270
_database_code_depnum_ccdc_archive 'CCDC 1995554'
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT077_A25_BA75_270        
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)acetylene molecules.
;
_vrf_PLAT906_A25_BA75_270        
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.037 Check 
RESPONSE: Due to loss of high angle diffraction peaks.
;
_vrf_PLAT911_A25_BA75_270        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         17 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2020-02-26T14:20:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C17.31 H14 N2.69 O2'
_chemical_formula_weight         291.69

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.18740(15)
_cell_length_b                   9.79793(17)
_cell_length_c                   10.95147(18)
_cell_angle_alpha                92.5603(14)
_cell_angle_beta                 107.7674(16)
_cell_angle_gamma                114.3678(17)
_cell_volume                     747.21(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    12877
_cell_measurement_theta_min      4.311
_cell_measurement_theta_max      75.254

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.103
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             305
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -1 0 0.0411
-3 5 4 0.0981
-1 -3 7 0.0767
1 3 -7 0.0786
2 -1 -7 0.0773
4 1 0 0.0599
2 -6 2 0.0625
0 -5 -2 0.0599
4 -1 -6 0.0847
3 -4 4 0.0491
-5 2 4 0.0882
1 -6 -1 0.0572
0 6 -2 0.0472
-2 6 -2 0.0453
1 -5 5 0.0477


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.706
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.484
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.931

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      270(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.1809055
_diffrn_orient_matrix_ub_12      -0.1485695
_diffrn_orient_matrix_ub_13      -0.0770776
_diffrn_orient_matrix_ub_21      -0.1269377
_diffrn_orient_matrix_ub_22      0.0733903
_diffrn_orient_matrix_ub_23      0.0187727
_diffrn_orient_matrix_ub_31      -0.0021791
_diffrn_orient_matrix_ub_32      0.0594445
_diffrn_orient_matrix_ub_33      -0.1280808
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_number            23782
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.324
_diffrn_reflns_theta_max         77.316
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.946
_reflns_Friedel_coverage         0
_reflns_number_total             3010
_reflns_number_gt                2464
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²+0.0669P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0054(10)
_refine_ls_number_reflns         3010
_refine_ls_number_parameters     284
_refine_ls_number_restraints     519
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1225
_refine_ls_wR_factor_gt          0.1148
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.034

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)acetylene and the pedal motion about the azo group and pyridyl
 rings, the atom sites N2 < N4 and C12 < C16, were split into parts A and B.
 These sites were allowed to free refine their site occupancies to a total 
 value of 1. To help maintain reasonable ADP and bond lengths, SIMU, RIGU, and 
 DFIX restraints and constraints were applied. At this temperature the ratio of 
 4,4'-azopyridine to bis(4-pyridyl)acetylene was 0.30 to 0.66 with the amount 
 of 4,4'-azopyridine in the secondary position calculated at 0.04. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16897(13) 0.14699(11) 0.30715(9) 0.0655(3) Uani 1 1 d . . . . .
H1 H 0.200864 0.171314 0.386539 0.098 Uiso 1 1 calc R U . . .
O2 O 0.81543(14) 0.21171(13) 0.43353(10) 0.0755(3) Uani 1 1 d . . . . .
H2A H 0.822367 0.250651 0.503933 0.113 Uiso 1 1 calc R U . . .
N1 N 0.26230(16) 0.24285(14) -0.42940(12) 0.0662(3) Uani 1 1 d . . . . .
C1 C 0.31904(18) 0.14697(13) 0.27840(12) 0.0541(3) Uani 1 1 d . . . . .
C2 C 0.49153(18) 0.17794(13) 0.37483(12) 0.0542(3) Uani 1 1 d . . . . .
H2 H 0.506589 0.198837 0.462331 0.065 Uiso 1 1 calc R U . . .
C3 C 0.64265(19) 0.17806(14) 0.34195(13) 0.0582(3) Uani 1 1 d . . . . .
C4 C 0.6184(2) 0.14305(16) 0.21154(14) 0.0681(4) Uani 1 1 d . . . . .
H4 H 0.717508 0.140231 0.188507 0.082 Uiso 1 1 calc R U . . .
C5 C 0.4460(2) 0.11258(17) 0.11681(14) 0.0716(4) Uani 1 1 d . . . . .
H5 H 0.43019 0.090032 0.029356 0.086 Uiso 1 1 calc R U . . .
C6 C 0.2957(2) 0.11448(15) 0.14769(13) 0.0655(4) Uani 1 1 d . . . . .
H6 H 0.180521 0.09433 0.082044 0.079 Uiso 1 1 calc R U . . .
C7 C 0.3292(2) 0.39178(17) -0.38607(15) 0.0695(4) Uani 1 1 d . . . . .
H7 H 0.377107 0.459033 -0.437825 0.083 Uiso 1 1 calc R U . . .
C8 C 0.3316(2) 0.45158(16) -0.26985(15) 0.0657(4) Uani 1 1 d . . . . .
H8 H 0.381771 0.556623 -0.242993 0.079 Uiso 1 1 calc R U . . .
C9 C 0.25765(17) 0.35220(15) -0.19306(13) 0.0558(3) Uani 1 1 d D . . . .
C10 C 0.19016(19) 0.19691(15) -0.23595(14) 0.0607(3) Uani 1 1 d . . . . .
H10 H 0.141623 0.126959 -0.186226 0.073 Uiso 1 1 calc R U . . .
C11 C 0.1965(2) 0.14860(16) -0.35337(14) 0.0640(4) Uani 1 1 d . . . . .
H11 H 0.152418 0.044486 -0.381158 0.077 Uiso 1 1 calc R U . . .
N2A N 0.223(2) 0.3832(13) -0.0655(13) 0.059(2) Uani 0.301(3) 1 d D U P A 1
N3A N 0.2586(12) 0.5040(9) -0.0110(9) 0.0654(16) Uani 0.301(3) 1 d D U P A 1
C12A C 0.229(2) 0.5535(13) 0.1055(11) 0.0522(16) Uani 0.301(3) 1 d . U P A 1
C13A C 0.279(2) 0.7026(13) 0.1572(12) 0.0604(19) Uani 0.301(3) 1 d . U P A 1
H13A H 0.334326 0.783445 0.118315 0.073 Uiso 0.301(3) 1 calc R U P A 1
C14A C 0.242(2) 0.7249(10) 0.2696(12) 0.0564(16) Uani 0.301(3) 1 d . U P A 1
H14A H 0.278049 0.826234 0.30259 0.068 Uiso 0.301(3) 1 calc R U P A 1
N4A N 0.173(2) 0.6365(12) 0.3309(11) 0.0623(19) Uani 0.301(3) 1 d . U P A 1
C15A C 0.1247(17) 0.5053(11) 0.2810(11) 0.0578(18) Uani 0.301(3) 1 d . U P A 1
H15A H 0.063514 0.43089 0.323119 0.069 Uiso 0.301(3) 1 calc R U P A 1
C16A C 0.1466(17) 0.4503(10) 0.1723(10) 0.0594(19) Uani 0.301(3) 1 d . U P A 1
H16A H 0.106312 0.346526 0.146007 0.071 Uiso 0.301(3) 1 calc R U P A 1
C12B C 0.2113(7) 0.5251(4) 0.1243(4) 0.0501(10) Uani 0.699(3) 1 d DG U P A 2
C13B C 0.2792(8) 0.6828(4) 0.1493(4) 0.0599(10) Uani 0.699(3) 1 d G U P A 2
H13B H 0.337319 0.741189 0.096261 0.072 Uiso 0.699(3) 1 calc R U P A 2
C14B C 0.2601(8) 0.7533(3) 0.2536(5) 0.0585(10) Uani 0.699(3) 1 d G U P A 2
H14B H 0.305471 0.858789 0.270274 0.07 Uiso 0.699(3) 1 calc R U P A 2
N4B N 0.1732(8) 0.6660(4) 0.3328(4) 0.0581(9) Uani 0.699(3) 1 d G U P A 2
C15B C 0.1053(7) 0.5083(4) 0.3078(4) 0.0592(9) Uani 0.699(3) 1 d G U P A 2
H15B H 0.047144 0.449967 0.360863 0.071 Uiso 0.699(3) 1 calc R U P A 2
C16B C 0.1244(6) 0.4379(3) 0.2036(4) 0.0550(9) Uani 0.699(3) 1 d G U P A 2
H16B H 0.07899 0.332364 0.18685 0.066 Uiso 0.699(3) 1 calc R U P A 2
C17 C 0.2316(7) 0.4586(6) 0.0164(4) 0.0539(8) Uani 0.656(3) 1 d D U P A 2
C18 C 0.2529(11) 0.4158(7) -0.0794(7) 0.0568(12) Uani 0.656(3) 1 d D U P A 2
N2B N 0.286(5) 0.481(5) -0.067(5) 0.061(4) Uani 0.043(3) 1 d D U P A 3
N3B N 0.174(5) 0.386(5) -0.021(5) 0.063(5) Uani 0.043(3) 1 d D U P A 3



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3583(15) . ?
O1 H1 0.82 . ?
O2 C3 1.3548(17) . ?
O2 H2A 0.82 . ?
N1 C11 1.3299(19) . ?
N1 C7 1.3320(19) . ?
C1 C2 1.3818(18) . ?
C1 C6 1.3889(18) . ?
C2 C3 1.3897(18) . ?
C2 H2 0.93 . ?
C3 C4 1.3872(19) . ?
C4 C5 1.375(2) . ?
C4 H4 0.93 . ?
C5 C6 1.379(2) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.368(2) . ?
C7 H7 0.93 . ?
C8 C9 1.385(2) . ?
C8 H8 0.93 . ?
C9 C18 1.386(7) . ?
C9 C10 1.3875(18) . ?
C9 N2A 1.548(14) . ?
C9 N2B 1.72(6) . ?
C10 C11 1.3736(19) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
N2A N3A 1.179(14) . ?
N3A C12A 1.467(14) . ?
C12A C16A 1.348(10) . ?
C12A C13A 1.383(9) . ?
C13A C14A 1.382(10) . ?
C13A H13A 0.93 . ?
C14A N4A 1.185(10) . ?
C14A C15A 1.990(11) . ?
C14A H14A 0.93 . ?
N4A C15A 1.222(10) . ?
C15A C16A 1.376(10) . ?
C15A H15A 0.93 . ?
C16A H16A 0.93 . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
C12B C17 1.410(5) . ?
C13B C14B 1.39 . ?
C13B H13B 0.93 . ?
C14B N4B 1.39 . ?
C14B H14B 0.93 . ?
N4B C15B 1.39 . ?
C15B C16B 1.39 . ?
C15B H15B 0.93 . ?
C16B H16B 0.93 . ?
C17 C18 1.200(8) . ?
N2B N3B 1.25(2) . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 117.23(12) . . ?
O1 C1 C2 121.94(11) . . ?
O1 C1 C6 118.19(12) . . ?
C2 C1 C6 119.87(13) . . ?
C1 C2 C3 120.45(12) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C4 118.09(12) . . ?
O2 C3 C2 122.18(12) . . ?
C4 C3 C2 119.73(13) . . ?
C5 C4 C3 119.06(13) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.92(13) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.94(14) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.81(14) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.54(13) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C8 C9 C18 117.1(3) . . ?
C8 C9 C10 118.28(12) . . ?
C18 C9 C10 124.6(3) . . ?
C8 C9 N2A 130.5(5) . . ?
C10 C9 N2A 111.1(5) . . ?
C8 C9 N2B 99.9(11) . . ?
C10 C9 N2B 141.8(11) . . ?
C11 C10 C9 118.64(13) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
N1 C11 C10 123.46(13) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
N3A N2A C9 125.5(14) . . ?
N2A N3A C12A 132.9(14) . . ?
C16A C12A C13A 114.0(6) . . ?
C16A C12A N3A 120.4(9) . . ?
C13A C12A N3A 125.6(9) . . ?
C14A C13A C12A 116.4(7) . . ?
C14A C13A H13A 121.8 . . ?
C12A C13A H13A 121.8 . . ?
N4A C14A C13A 130.7(7) . . ?
N4A C14A C15A 34.8(4) . . ?
C13A C14A C15A 95.9(5) . . ?
N4A C14A H14A 114.6 . . ?
C13A C14A H14A 114.6 . . ?
C15A C14A H14A 149.4 . . ?
C14A N4A C15A 111.6(7) . . ?
N4A C15A C16A 130.2(7) . . ?
N4A C15A C14A 33.6(3) . . ?
C16A C15A C14A 96.6(5) . . ?
N4A C15A H15A 114.9 . . ?
C16A C15A H15A 114.9 . . ?
C14A C15A H15A 148.5 . . ?
C12A C16A C15A 117.1(6) . . ?
C12A C16A H16A 121.5 . . ?
C15A C16A H16A 121.5 . . ?
C13B C12B C16B 120 . . ?
C13B C12B C17 118.0(3) . . ?
C16B C12B C17 122.0(3) . . ?
C14B C13B C12B 120 . . ?
C14B C13B H13B 120 . . ?
C12B C13B H13B 120 . . ?
C13B C14B N4B 120 . . ?
C13B C14B H14B 120 . . ?
N4B C14B H14B 120 . . ?
C15B N4B C14B 120 . . ?
C16B C15B N4B 120 . . ?
C16B C15B H15B 120 . . ?
N4B C15B H15B 120 . . ?
C15B C16B C12B 120 . . ?
C15B C16B H16B 120 . . ?
C12B C16B H16B 120 . . ?
C18 C17 C12B 173.4(6) . . ?
C17 C18 C9 173.5(7) . . ?
N3B N2B C9 97(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
O1 C1 C2 C3 -179.53(11) . . . . ?
C6 C1 C2 C3 0.53(19) . . . . ?
C1 C2 C3 O2 178.27(11) . . . . ?
C1 C2 C3 C4 -1.64(19) . . . . ?
O2 C3 C4 C5 -178.26(13) . . . . ?
C2 C3 C4 C5 1.7(2) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
O1 C1 C6 C5 -179.40(12) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
C11 N1 C7 C8 -0.8(2) . . . . ?
N1 C7 C8 C9 -1.1(2) . . . . ?
C7 C8 C9 C18 -176.7(4) . . . . ?
C7 C8 C9 C10 2.0(2) . . . . ?
C7 C8 C9 N2A -173.5(8) . . . . ?
C7 C8 C9 N2B -177.8(15) . . . . ?
C8 C9 C10 C11 -1.15(19) . . . . ?
C18 C9 C10 C11 177.4(4) . . . . ?
N2A C9 C10 C11 175.2(6) . . . . ?
N2B C9 C10 C11 178(2) . . . . ?
C7 N1 C11 C10 1.7(2) . . . . ?
C9 C10 C11 N1 -0.7(2) . . . . ?
C8 C9 N2A N3A -1(2) . . . . ?
C10 C9 N2A N3A -176.5(13) . . . . ?
C9 N2A N3A C12A 177.1(11) . . . . ?
N2A N3A C12A C16A 0(2) . . . . ?
N2A N3A C12A C13A -179.6(14) . . . . ?
C16A C12A C13A C14A 1.5(8) . . . . ?
N3A C12A C13A C14A -178.7(13) . . . . ?
C12A C13A C14A N4A -0.4(10) . . . . ?
C12A C13A C14A C15A -1.4(6) . . . . ?
C13A C14A N4A C15A -1.7(10) . . . . ?
C14A N4A C15A C16A 3.0(10) . . . . ?
C13A C12A C16A C15A -0.5(8) . . . . ?
N3A C12A C16A C15A 179.6(12) . . . . ?
N4A C15A C16A C12A -2.0(10) . . . . ?
C14A C15A C16A C12A -0.3(6) . . . . ?
C16B C12B C13B C14B 0 . . . . ?
C17 C12B C13B C14B 179.2(5) . . . . ?
C12B C13B C14B N4B 0 . . . . ?
C13B C14B N4B C15B 0 . . . . ?
C14B N4B C15B C16B 0 . . . . ?
N4B C15B C16B C12B 0 . . . . ?
C13B C12B C16B C15B 0 . . . . ?
C17 C12B C16B C15B -179.1(5) . . . . ?
C8 C9 N2B N3B 163(3) . . . . ?
C10 C9 N2B N3B -16(5) . . . . ?

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
O1 H1 N1 0.82 1.94 2.7587(15) 173.8 1_556 yes
O2 H2A N4A 0.82 2.06 2.875(9) 173.5 2_666 yes
O2 H2A N4B 0.82 1.92 2.73(2) 177.3 2_666 yes

####################################################################### 
# 
# 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_A25_BA75_230
_database_code_depnum_ccdc_archive 'CCDC 1995552'
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;


# start Validation Reply Form
_vrf_PLAT077_A25_BA75_230        
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)acetylene molecules.
;
_vrf_PLAT992_A25_BA75_230        
;
PROBLEM: Repd & Actual _reflns_number_gt Values Differ by         11 Check 
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2020-02-26T14:18:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C17.35 H14 N2.65 O2'
_chemical_formula_weight         291.62

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.15991(18)
_cell_length_b                   9.7782(2)
_cell_length_c                   10.9363(3)
_cell_angle_alpha                92.3422(18)
_cell_angle_beta                 107.888(2)
_cell_angle_gamma                114.448(2)
_cell_volume                     741.61(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    14716
_cell_measurement_theta_min      4.319
_cell_measurement_theta_max      76.322

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.103
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             305
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -1 0 0.0411
-3 5 4 0.0981
-1 -3 7 0.0767
1 3 -7 0.0786
2 -1 -7 0.0773
4 1 0 0.0599
2 -6 2 0.0625
0 -5 -2 0.0599
4 -1 -6 0.0847
3 -4 4 0.0491
-5 2 4 0.0882
1 -6 -1 0.0572
0 6 -2 0.0472
-2 6 -2 0.0453
1 -5 5 0.0477


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.575
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.871
_shelx_estimated_absorpt_T_max   0.93

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      230(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.1811818
_diffrn_orient_matrix_ub_12      -0.1494171
_diffrn_orient_matrix_ub_13      -0.0766025
_diffrn_orient_matrix_ub_21      -0.128172
_diffrn_orient_matrix_ub_22      0.0727099
_diffrn_orient_matrix_ub_23      0.018439
_diffrn_orient_matrix_ub_31      -0.0032382
_diffrn_orient_matrix_ub_32      0.0592531
_diffrn_orient_matrix_ub_33      -0.1286802
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0731
_diffrn_reflns_number            24585
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.33
_diffrn_reflns_theta_max         77.422
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.954
_reflns_Friedel_coverage         0
_reflns_number_total             3016
_reflns_number_gt                2570
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0614P)²+0.0746P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0048(10)
_refine_ls_number_reflns         3016
_refine_ls_number_parameters     284
_refine_ls_number_restraints     513
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1172
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.034

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)acetylene and the pedal motion about the azo group and pyridyl
 rings, the atom sites N2 < N4 and C12 < C16, were split into parts A and B.
 These sites were allowed to free refine their site occupancies to a total 
 value of 1. To help maintain reasonable ADP and bond lengths, SIMU, RIGU, and 
 DFIX restraints and constraints were applied. At this temperature the ratio of 
 4,4'-azopyridine to bis(4-pyridyl)acetylene was 0.30 to 0.67 with the amount 
 of 4,4'-azopyridine in the secondary position calculated at 0.03. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16772(12) 0.14772(10) 0.30704(9) 0.0562(3) Uani 1 1 d . . . . .
H1 H 0.200916 0.173795 0.387392 0.084 Uiso 1 1 calc R U . . .
O2 O 0.81683(13) 0.21145(12) 0.43421(9) 0.0647(3) Uani 1 1 d . . . . .
H2A H 0.824731 0.252195 0.505234 0.097 Uiso 1 1 calc R U . . .
N1 N 0.26242(15) 0.24312(13) -0.42960(11) 0.0578(3) Uani 1 1 d . . . . .
C1 C 0.31808(17) 0.14744(12) 0.27825(11) 0.0467(3) Uani 1 1 d . . . . .
C2 C 0.49175(17) 0.17829(12) 0.37533(11) 0.0471(3) Uani 1 1 d . . . . .
H2 H 0.507228 0.199492 0.46388 0.057 Uiso 1 1 calc R U . . .
C3 C 0.64316(18) 0.17800(13) 0.34230(12) 0.0505(3) Uani 1 1 d . . . . .
C4 C 0.6190(2) 0.14282(15) 0.21162(13) 0.0585(3) Uani 1 1 d . . . . .
H4 H 0.719436 0.139782 0.188489 0.07 Uiso 1 1 calc R U . . .
C5 C 0.4452(2) 0.11244(15) 0.11636(13) 0.0615(4) Uani 1 1 d . . . . .
H5 H 0.42892 0.089495 0.027853 0.074 Uiso 1 1 calc R U . . .
C6 C 0.2945(2) 0.11477(14) 0.14733(12) 0.0563(3) Uani 1 1 d . . . . .
H6 H 0.177579 0.094559 0.080833 0.068 Uiso 1 1 calc R U . . .
C7 C 0.32954(19) 0.39281(16) -0.38640(14) 0.0607(3) Uani 1 1 d . . . . .
H7 H 0.377804 0.461219 -0.438852 0.073 Uiso 1 1 calc R U . . .
C8 C 0.33179(19) 0.45201(15) -0.26964(14) 0.0580(3) Uani 1 1 d . . . . .
H8 H 0.382476 0.558323 -0.24241 0.07 Uiso 1 1 calc R U . . .
C9 C 0.25789(16) 0.35199(14) -0.19263(12) 0.0492(3) Uani 1 1 d D . . . .
C10 C 0.18987(18) 0.19593(14) -0.23564(12) 0.0522(3) Uani 1 1 d . . . . .
H10 H 0.14052 0.124767 -0.185393 0.063 Uiso 1 1 calc R U . . .
C11 C 0.19650(18) 0.14827(15) -0.35317(13) 0.0551(3) Uani 1 1 d . . . . .
H11 H 0.152081 0.042907 -0.381214 0.066 Uiso 1 1 calc R U . . .
N2A N 0.2209(16) 0.3818(10) -0.0627(11) 0.0504(18) Uani 0.297(3) 1 d D U P A 1
N3A N 0.2603(10) 0.5064(7) -0.0137(7) 0.0568(14) Uani 0.297(3) 1 d D U P A 1
C12A C 0.2281(19) 0.5513(13) 0.1029(11) 0.0464(15) Uani 0.297(3) 1 d . U P A 1
C13A C 0.281(2) 0.7032(13) 0.1552(12) 0.0528(19) Uani 0.297(3) 1 d . U P A 1
H13A H 0.338157 0.784888 0.115952 0.063 Uiso 0.297(3) 1 calc R U P A 1
C14A C 0.243(2) 0.7264(10) 0.2674(12) 0.0483(16) Uani 0.297(3) 1 d . U P A 1
H14A H 0.280727 0.829226 0.300385 0.058 Uiso 0.297(3) 1 calc R U P A 1
N4A N 0.172(2) 0.6379(11) 0.3294(11) 0.0532(17) Uani 0.297(3) 1 d . U P A 1
C15A C 0.1227(15) 0.5043(10) 0.2790(10) 0.0491(17) Uani 0.297(3) 1 d . U P A 1
H15A H 0.060834 0.429017 0.321913 0.059 Uiso 0.297(3) 1 calc R U P A 1
C16A C 0.1444(16) 0.4492(10) 0.1699(9) 0.0520(18) Uani 0.297(3) 1 d . U P A 1
H16A H 0.102088 0.343903 0.143408 0.062 Uiso 0.297(3) 1 calc R U P A 1
C12B C 0.2121(7) 0.5269(4) 0.1249(3) 0.0432(9) Uani 0.703(3) 1 d DG U P A 2
C13B C 0.2797(8) 0.6848(4) 0.1501(4) 0.0519(10) Uani 0.703(3) 1 d G U P A 2
H13B H 0.338893 0.744506 0.096633 0.062 Uiso 0.703(3) 1 calc R U P A 2
C14B C 0.2597(9) 0.7544(3) 0.2543(5) 0.0501(9) Uani 0.703(3) 1 d G U P A 2
H14B H 0.305389 0.861241 0.271332 0.06 Uiso 0.703(3) 1 calc R U P A 2
N4B N 0.1721(8) 0.6661(4) 0.3333(4) 0.0501(8) Uani 0.703(3) 1 d G U P A 2
C15B C 0.1046(6) 0.5082(4) 0.3081(3) 0.0510(8) Uani 0.703(3) 1 d G U P A 2
H15B H 0.04538 0.448481 0.361515 0.061 Uiso 0.703(3) 1 calc R U P A 2
C16B C 0.1246(6) 0.4386(3) 0.2039(3) 0.0472(8) Uani 0.703(3) 1 d G U P A 2
H16B H 0.078883 0.331743 0.186816 0.057 Uiso 0.703(3) 1 calc R U P A 2
C17 C 0.2325(5) 0.4603(5) 0.0165(3) 0.0461(7) Uani 0.673(3) 1 d D U P A 2
C18 C 0.2523(8) 0.4143(6) -0.0793(5) 0.0486(10) Uani 0.673(3) 1 d D U P A 2
N2B N 0.294(7) 0.470(6) -0.067(6) 0.051(4) Uani 0.030(3) 1 d D U P A 3
N3B N 0.167(6) 0.394(6) -0.022(6) 0.051(5) Uani 0.030(3) 1 d D U P A 3



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3582(15) . ?
O1 H1 0.83 . ?
O2 C3 1.3564(15) . ?
O2 H2A 0.83 . ?
N1 C11 1.3323(18) . ?
N1 C7 1.3367(17) . ?
C1 C2 1.3864(17) . ?
C1 C6 1.3897(17) . ?
C2 C3 1.3906(17) . ?
C2 H2 0.94 . ?
C3 C4 1.3893(18) . ?
C4 C5 1.380(2) . ?
C4 H4 0.94 . ?
C5 C6 1.381(2) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.372(2) . ?
C7 H7 0.94 . ?
C8 C9 1.3859(19) . ?
C8 H8 0.94 . ?
C9 C18 1.381(6) . ?
C9 C10 1.3921(17) . ?
C9 N2A 1.581(11) . ?
C9 N2B 1.63(7) . ?
C10 C11 1.3736(17) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
N2A N3A 1.180(12) . ?
N3A C12A 1.464(12) . ?
C12A C16A 1.342(9) . ?
C12A C13A 1.403(9) . ?
C13A C14A 1.384(9) . ?
C13A H13A 0.94 . ?
C14A N4A 1.191(10) . ?
C14A C15A 2.007(11) . ?
C14A H14A 0.94 . ?
N4A C15A 1.241(9) . ?
C15A C16A 1.379(9) . ?
C15A H15A 0.94 . ?
C16A H16A 0.94 . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
C12B C17 1.416(4) . ?
C13B C14B 1.39 . ?
C13B H13B 0.94 . ?
C14B N4B 1.39 . ?
C14B H14B 0.94 . ?
N4B C15B 1.39 . ?
C15B C16B 1.39 . ?
C15B H15B 0.94 . ?
C16B H16B 0.94 . ?
C17 C18 1.204(7) . ?
N2B N3B 1.25(2) . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 117.27(11) . . ?
O1 C1 C2 121.83(11) . . ?
O1 C1 C6 118.26(11) . . ?
C2 C1 C6 119.91(12) . . ?
C1 C2 C3 120.31(11) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C4 117.97(11) . . ?
O2 C3 C2 122.09(11) . . ?
C4 C3 C2 119.94(12) . . ?
C5 C4 C3 118.92(12) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.88(12) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.02(12) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.54(13) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 118.70(12) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C18 C9 C8 117.3(2) . . ?
C18 C9 C10 124.3(2) . . ?
C8 C9 C10 118.33(12) . . ?
C8 C9 N2A 130.9(4) . . ?
C10 C9 N2A 110.7(3) . . ?
C8 C9 N2B 101.7(16) . . ?
C10 C9 N2B 139.8(17) . . ?
C11 C10 C9 118.50(12) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
N1 C11 C10 123.62(12) . . ?
N1 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
N3A N2A C9 121.2(10) . . ?
N2A N3A C12A 127.5(11) . . ?
C16A C12A C13A 113.7(6) . . ?
C16A C12A N3A 122.5(8) . . ?
C13A C12A N3A 123.7(9) . . ?
C14A C13A C12A 116.5(7) . . ?
C14A C13A H13A 121.8 . . ?
C12A C13A H13A 121.8 . . ?
N4A C14A C13A 130.8(7) . . ?
N4A C14A C15A 35.2(4) . . ?
C13A C14A C15A 95.6(5) . . ?
N4A C14A H14A 114.6 . . ?
C13A C14A H14A 114.6 . . ?
C15A C14A H14A 149.8 . . ?
C14A N4A C15A 111.2(6) . . ?
N4A C15A C16A 130.1(7) . . ?
N4A C15A C14A 33.6(3) . . ?
C16A C15A C14A 96.5(5) . . ?
N4A C15A H15A 115 . . ?
C16A C15A H15A 115 . . ?
C14A C15A H15A 148.5 . . ?
C12A C16A C15A 117.7(5) . . ?
C12A C16A H16A 121.2 . . ?
C15A C16A H16A 121.2 . . ?
C13B C12B C16B 120 . . ?
C13B C12B C17 118.2(3) . . ?
C16B C12B C17 121.8(3) . . ?
C14B C13B C12B 120 . . ?
C14B C13B H13B 120 . . ?
C12B C13B H13B 120 . . ?
N4B C14B C13B 120 . . ?
N4B C14B H14B 120 . . ?
C13B C14B H14B 120 . . ?
C14B N4B C15B 120 . . ?
C16B C15B N4B 120 . . ?
C16B C15B H15B 120 . . ?
N4B C15B H15B 120 . . ?
C15B C16B C12B 120 . . ?
C15B C16B H16B 120 . . ?
C12B C16B H16B 120 . . ?
C18 C17 C12B 174.8(5) . . ?
C17 C18 C9 174.9(6) . . ?
N3B N2B C9 104(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -179.59(10) . . . . ?
C6 C1 C2 C3 0.55(17) . . . . ?
C1 C2 C3 O2 178.27(11) . . . . ?
C1 C2 C3 C4 -1.65(18) . . . . ?
O2 C3 C4 C5 -178.29(12) . . . . ?
C2 C3 C4 C5 1.63(19) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
O1 C1 C6 C5 -179.33(11) . . . . ?
C2 C1 C6 C5 0.53(18) . . . . ?
C11 N1 C7 C8 -0.67(19) . . . . ?
N1 C7 C8 C9 -1.1(2) . . . . ?
C7 C8 C9 C18 -176.5(3) . . . . ?
C7 C8 C9 C10 1.89(18) . . . . ?
C7 C8 C9 N2A -173.1(6) . . . . ?
C7 C8 C9 N2B 179(2) . . . . ?
C18 C9 C10 C11 177.3(3) . . . . ?
C8 C9 C10 C11 -0.97(18) . . . . ?
N2A C9 C10 C11 175.0(5) . . . . ?
N2B C9 C10 C11 -176(3) . . . . ?
C7 N1 C11 C10 1.69(19) . . . . ?
C9 C10 C11 N1 -0.87(19) . . . . ?
C8 C9 N2A N3A -1.2(14) . . . . ?
C10 C9 N2A N3A -176.5(9) . . . . ?
C9 N2A N3A C12A 177.5(9) . . . . ?
N2A N3A C12A C16A -0.4(17) . . . . ?
N2A N3A C12A C13A 179.7(11) . . . . ?
C16A C12A C13A C14A 1.3(7) . . . . ?
N3A C12A C13A C14A -178.8(12) . . . . ?
C12A C13A C14A N4A -0.3(9) . . . . ?
C12A C13A C14A C15A -1.1(5) . . . . ?
C13A C14A N4A C15A -1.5(9) . . . . ?
C14A N4A C15A C16A 2.4(9) . . . . ?
C13A C12A C16A C15A -0.6(8) . . . . ?
N3A C12A C16A C15A 179.5(11) . . . . ?
N4A C15A C16A C12A -1.4(10) . . . . ?
C14A C15A C16A C12A -0.1(6) . . . . ?
C16B C12B C13B C14B 0 . . . . ?
C17 C12B C13B C14B 179.0(4) . . . . ?
C12B C13B C14B N4B 0 . . . . ?
C13B C14B N4B C15B 0 . . . . ?
C14B N4B C15B C16B 0 . . . . ?
N4B C15B C16B C12B 0 . . . . ?
C13B C12B C16B C15B 0 . . . . ?
C17 C12B C16B C15B -179.0(5) . . . . ?
C8 C9 N2B N3B 154(4) . . . . ?
C10 C9 N2B N3B -31(6) . . . . ?

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
O1 H1 N1 0.83 1.93 2.7530(14) 174.7 1_556 yes
O2 H2A N4A 0.83 2.05 2.881(9) 174.4 2_666 yes
O2 H2A N4B 0.83 1.9 2.73(2) 176.2 2_666 yes

####################################################################### 
# 
# 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_A25_BA75_290
_database_code_depnum_ccdc_archive 'CCDC 1995555'
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT077_A25_BA75_290        
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)acetylene molecules.
;
_vrf_PLAT906_A25_BA75_290        
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.102 Check 
RESPONSE: Due to loss of high angle diffraction peaks.
;
_vrf_PLAT911_A25_BA75_290        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         26 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2020-02-26T14:20:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C17.31 H14 N2.69 O2'
_chemical_formula_weight         291.69

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.20177(17)
_cell_length_b                   9.80593(19)
_cell_length_c                   10.9558(2)
_cell_angle_alpha                92.6345(16)
_cell_angle_beta                 107.7151(18)
_cell_angle_gamma                114.3297(19)
_cell_volume                     749.76(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    12613
_cell_measurement_theta_min      4.31
_cell_measurement_theta_max      75.141

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.103
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             305
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -1 0 0.0411
-3 5 4 0.0981
-1 -3 7 0.0767
1 3 -7 0.0786
2 -1 -7 0.0773
4 1 0 0.0599
2 -6 2 0.0625
0 -5 -2 0.0599
4 -1 -6 0.0847
3 -4 4 0.0491
-5 2 4 0.0882
1 -6 -1 0.0572
0 6 -2 0.0472
-2 6 -2 0.0453
1 -5 5 0.0477


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.575
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.931

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      290(2)
_diffrn_ambient_environment      air
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.1808599
_diffrn_orient_matrix_ub_12      -0.1480775
_diffrn_orient_matrix_ub_13      -0.0772491
_diffrn_orient_matrix_ub_21      -0.1261423
_diffrn_orient_matrix_ub_22      0.0738581
_diffrn_orient_matrix_ub_23      0.0190453
_diffrn_orient_matrix_ub_31      -0.0017357
_diffrn_orient_matrix_ub_32      0.0595902
_diffrn_orient_matrix_ub_33      -0.1278423
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.076
_diffrn_reflns_number            23104
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.321
_diffrn_reflns_theta_max         77.417
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.937
_diffrn_reflns_Laue_measured_fraction_full 0.99
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 0.99
_diffrn_reflns_point_group_measured_fraction_max 0.937
_reflns_Friedel_coverage         0
_reflns_number_total             2997
_reflns_number_gt                2385
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0650P)²+0.0471P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0051(10)
_refine_ls_number_reflns         2997
_refine_ls_number_parameters     284
_refine_ls_number_restraints     519
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.1143
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.031

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)acetylene and the pedal motion about the azo group and pyridyl
 rings, the atom sites N2 < N4 and C12 < C16, were split into parts A and B.
 These sites were allowed to free refine their site occupancies to a total 
 value of 1. To help maintain reasonable ADP and bond lengths, SIMU, RIGU, and 
 DFIX restraints and constraints were applied. At this temperature the ratio of 
 4,4'-azopyridine to bis(4-pyridyl)acetylene was 0.29 to 0.66 with the amount 
 of 4,4'-azopyridine in the secondary position calculated at 0.05. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16961(13) 0.14671(11) 0.30728(9) 0.0703(3) Uani 1 1 d . . . . .
H1 H 0.201677 0.171658 0.386592 0.105 Uiso 1 1 calc R U . . .
O2 O 0.81463(14) 0.21173(13) 0.43318(10) 0.0810(3) Uani 1 1 d . . . . .
H2A H 0.820748 0.249008 0.503947 0.121 Uiso 1 1 calc R U . . .
N1 N 0.26217(16) 0.24253(14) -0.42911(11) 0.0708(3) Uani 1 1 d . . . . .
C1 C 0.31938(18) 0.14667(13) 0.27844(12) 0.0577(3) Uani 1 1 d . . . . .
C2 C 0.49175(18) 0.17794(13) 0.37485(12) 0.0577(3) Uani 1 1 d . . . . .
H2 H 0.506834 0.199056 0.462316 0.069 Uiso 1 1 calc R U . . .
C3 C 0.64235(19) 0.17802(14) 0.34196(13) 0.0623(3) Uani 1 1 d . . . . .
C4 C 0.6183(2) 0.14317(16) 0.21138(15) 0.0732(4) Uani 1 1 d . . . . .
H4 H 0.717202 0.140573 0.188229 0.088 Uiso 1 1 calc R U . . .
C5 C 0.4462(2) 0.11262(17) 0.11698(14) 0.0769(4) Uani 1 1 d . . . . .
H5 H 0.430409 0.090115 0.029539 0.092 Uiso 1 1 calc R U . . .
C6 C 0.2964(2) 0.11431(15) 0.14788(13) 0.0696(4) Uani 1 1 d . . . . .
H6 H 0.181428 0.094079 0.082278 0.083 Uiso 1 1 calc R U . . .
C7 C 0.3292(2) 0.39156(17) -0.38610(15) 0.0738(4) Uani 1 1 d . . . . .
H7 H 0.37701 0.458578 -0.437874 0.089 Uiso 1 1 calc R U . . .
C8 C 0.3314(2) 0.45129(16) -0.26992(15) 0.0699(4) Uani 1 1 d . . . . .
H8 H 0.381414 0.556242 -0.243051 0.084 Uiso 1 1 calc R U . . .
C9 C 0.25774(17) 0.35240(15) -0.19334(12) 0.0591(3) Uani 1 1 d D . . . .
C10 C 0.19008(19) 0.19703(15) -0.23601(13) 0.0646(3) Uani 1 1 d . . . . .
H10 H 0.141554 0.127297 -0.186276 0.078 Uiso 1 1 calc R U . . .
C11 C 0.1965(2) 0.14884(16) -0.35309(14) 0.0687(4) Uani 1 1 d . . . . .
H11 H 0.152391 0.044788 -0.380858 0.082 Uiso 1 1 calc R U . . .
N2A N 0.2219(19) 0.3825(13) -0.0651(13) 0.063(2) Uani 0.294(3) 1 d D U P A 1
N3A N 0.2581(12) 0.5037(9) -0.0116(10) 0.0676(17) Uani 0.294(3) 1 d D U P A 1
C12A C 0.227(2) 0.5526(14) 0.1050(11) 0.0557(16) Uani 0.294(3) 1 d . U P A 1
C13A C 0.280(2) 0.7026(13) 0.1586(12) 0.0645(19) Uani 0.294(3) 1 d . U P A 1
H13A H 0.336704 0.783692 0.120791 0.077 Uiso 0.294(3) 1 calc R U P A 1
C14A C 0.243(2) 0.7246(11) 0.2701(12) 0.0600(17) Uani 0.294(3) 1 d . U P A 1
H14A H 0.27996 0.825931 0.303504 0.072 Uiso 0.294(3) 1 calc R U P A 1
N4A N 0.173(2) 0.6368(12) 0.3312(11) 0.067(2) Uani 0.294(3) 1 d . U P A 1
C15A C 0.1239(18) 0.5062(12) 0.2804(11) 0.0630(19) Uani 0.294(3) 1 d . U P A 1
H15A H 0.062894 0.431893 0.322499 0.076 Uiso 0.294(3) 1 calc R U P A 1
C16A C 0.1439(18) 0.4509(11) 0.1720(11) 0.064(2) Uani 0.294(3) 1 d . U P A 1
H16A H 0.101419 0.346878 0.145391 0.077 Uiso 0.294(3) 1 calc R U P A 1
C12B C 0.2119(8) 0.5248(4) 0.1243(4) 0.0538(10) Uani 0.706(3) 1 d DG U P A 2
C13B C 0.2788(8) 0.6823(4) 0.1491(4) 0.0638(10) Uani 0.706(3) 1 d G U P A 2
H13B H 0.336439 0.740618 0.095955 0.077 Uiso 0.706(3) 1 calc R U P A 2
C14B C 0.2597(8) 0.7526(3) 0.2534(5) 0.0632(10) Uani 0.706(3) 1 d G U P A 2
H14B H 0.304428 0.857953 0.270043 0.076 Uiso 0.706(3) 1 calc R U P A 2
N4B N 0.1736(8) 0.6654(4) 0.3329(4) 0.0626(9) Uani 0.706(3) 1 d G U P A 2
C15B C 0.1066(7) 0.5079(4) 0.3080(4) 0.0633(9) Uani 0.706(3) 1 d G U P A 2
H15B H 0.049044 0.449601 0.361161 0.076 Uiso 0.706(3) 1 calc R U P A 2
C16B C 0.1258(7) 0.4376(3) 0.2037(4) 0.0595(9) Uani 0.706(3) 1 d G U P A 2
H16B H 0.081053 0.332263 0.187073 0.071 Uiso 0.706(3) 1 calc R U P A 2
C17 C 0.2316(7) 0.4587(6) 0.0163(4) 0.0576(9) Uani 0.655(3) 1 d D U P A 2
C18 C 0.2530(10) 0.4156(7) -0.0799(6) 0.0587(11) Uani 0.655(3) 1 d D U P A 2
N2B N 0.283(5) 0.479(5) -0.069(4) 0.064(4) Uani 0.051(3) 1 d D U P A 3
N3B N 0.181(5) 0.390(5) -0.014(4) 0.067(5) Uani 0.051(3) 1 d D U P A 3



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3584(15) . ?
O1 H1 0.82 . ?
O2 C3 1.3528(17) . ?
O2 H2A 0.82 . ?
N1 C11 1.3280(19) . ?
N1 C7 1.3330(18) . ?
C1 C2 1.3830(18) . ?
C1 C6 1.3881(18) . ?
C2 C3 1.3877(18) . ?
C2 H2 0.93 . ?
C3 C4 1.3893(19) . ?
C4 C5 1.373(2) . ?
C4 H4 0.93 . ?
C5 C6 1.376(2) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.368(2) . ?
C7 H7 0.93 . ?
C8 C9 1.382(2) . ?
C8 H8 0.93 . ?
C9 C18 1.382(7) . ?
C9 C10 1.3884(18) . ?
C9 N2A 1.560(13) . ?
C9 N2B 1.70(5) . ?
C10 C11 1.3701(18) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
N2A N3A 1.177(14) . ?
N3A C12A 1.471(14) . ?
C12A C16A 1.346(10) . ?
C12A C13A 1.392(9) . ?
C13A C14A 1.372(10) . ?
C13A H13A 0.93 . ?
C14A N4A 1.183(10) . ?
C14A C15A 1.979(12) . ?
C14A H14A 0.93 . ?
N4A C15A 1.219(10) . ?
C15A C16A 1.365(10) . ?
C15A H15A 0.93 . ?
C16A H16A 0.93 . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
C12B C17 1.406(5) . ?
C13B C14B 1.39 . ?
C13B H13B 0.93 . ?
C14B N4B 1.39 . ?
C14B H14B 0.93 . ?
N4B C15B 1.39 . ?
C15B C16B 1.39 . ?
C15B H15B 0.93 . ?
C16B H16B 0.93 . ?
C17 C18 1.206(8) . ?
N2B N3B 1.25(2) . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 117.29(12) . . ?
O1 C1 C2 121.92(11) . . ?
O1 C1 C6 118.25(12) . . ?
C2 C1 C6 119.83(13) . . ?
C1 C2 C3 120.44(12) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.24(12) . . ?
O2 C3 C4 118.03(12) . . ?
C2 C3 C4 119.72(13) . . ?
C5 C4 C3 119.00(13) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 122.00(13) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.99(14) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.57(14) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 118.61(13) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C18 C9 C8 117.2(3) . . ?
C18 C9 C10 124.3(3) . . ?
C8 C9 C10 118.42(12) . . ?
C8 C9 N2A 130.9(4) . . ?
C10 C9 N2A 110.5(4) . . ?
C8 C9 N2B 100.2(10) . . ?
C10 C9 N2B 141.3(10) . . ?
C11 C10 C9 118.45(13) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
N1 C11 C10 123.61(13) . . ?
N1 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
N3A N2A C9 124.4(13) . . ?
N2A N3A C12A 131.9(14) . . ?
C16A C12A C13A 113.1(7) . . ?
C16A C12A N3A 121.3(9) . . ?
C13A C12A N3A 125.7(10) . . ?
C14A C13A C12A 116.6(7) . . ?
C14A C13A H13A 121.7 . . ?
C12A C13A H13A 121.7 . . ?
N4A C14A C13A 131.1(7) . . ?
N4A C14A C15A 35.1(5) . . ?
C13A C14A C15A 96.0(5) . . ?
N4A C14A H14A 114.5 . . ?
C13A C14A H14A 114.5 . . ?
C15A C14A H14A 149.5 . . ?
C14A N4A C15A 111.0(7) . . ?
N4A C15A C16A 130.7(7) . . ?
N4A C15A C14A 33.9(3) . . ?
C16A C15A C14A 96.8(6) . . ?
N4A C15A H15A 114.7 . . ?
C16A C15A H15A 114.7 . . ?
C14A C15A H15A 148.5 . . ?
C12A C16A C15A 117.5(6) . . ?
C12A C16A H16A 121.2 . . ?
C15A C16A H16A 121.2 . . ?
C13B C12B C16B 120 . . ?
C13B C12B C17 117.9(3) . . ?
C16B C12B C17 122.1(3) . . ?
C14B C13B C12B 120 . . ?
C14B C13B H13B 120 . . ?
C12B C13B H13B 120 . . ?
N4B C14B C13B 120 . . ?
N4B C14B H14B 120 . . ?
C13B C14B H14B 120 . . ?
C15B N4B C14B 120 . . ?
N4B C15B C16B 120 . . ?
N4B C15B H15B 120 . . ?
C16B C15B H15B 120 . . ?
C15B C16B C12B 120 . . ?
C15B C16B H16B 120 . . ?
C12B C16B H16B 120 . . ?
C18 C17 C12B 173.6(6) . . ?
C17 C18 C9 173.6(7) . . ?
N3B N2B C9 101(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -179.54(11) . . . . ?
C6 C1 C2 C3 0.35(18) . . . . ?
C1 C2 C3 O2 178.33(11) . . . . ?
C1 C2 C3 C4 -1.41(19) . . . . ?
O2 C3 C4 C5 -178.27(13) . . . . ?
C2 C3 C4 C5 1.5(2) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
O1 C1 C6 C5 -179.50(12) . . . . ?
C2 C1 C6 C5 0.6(2) . . . . ?
C11 N1 C7 C8 -0.7(2) . . . . ?
N1 C7 C8 C9 -1.0(2) . . . . ?
C7 C8 C9 C18 -176.7(4) . . . . ?
C7 C8 C9 C10 1.9(2) . . . . ?
C7 C8 C9 N2A -173.4(7) . . . . ?
C7 C8 C9 N2B -177.2(13) . . . . ?
C18 C9 C10 C11 177.5(4) . . . . ?
C8 C9 C10 C11 -1.10(19) . . . . ?
N2A C9 C10 C11 175.1(6) . . . . ?
N2B C9 C10 C11 178(2) . . . . ?
C7 N1 C11 C10 1.6(2) . . . . ?
C9 C10 C11 N1 -0.7(2) . . . . ?
C8 C9 N2A N3A -1.0(19) . . . . ?
C10 C9 N2A N3A -176.6(12) . . . . ?
C9 N2A N3A C12A 177.0(11) . . . . ?
N2A N3A C12A C16A 0(2) . . . . ?
N2A N3A C12A C13A 179.4(14) . . . . ?
C16A C12A C13A C14A 1.2(8) . . . . ?
N3A C12A C13A C14A -178.2(13) . . . . ?
C12A C13A C14A N4A -0.1(11) . . . . ?
C12A C13A C14A C15A -1.0(6) . . . . ?
C13A C14A N4A C15A -1.7(10) . . . . ?
C14A N4A C15A C16A 2.5(10) . . . . ?
C13A C12A C16A C15A -0.6(9) . . . . ?
N3A C12A C16A C15A 178.8(12) . . . . ?
N4A C15A C16A C12A -1.4(11) . . . . ?
C14A C15A C16A C12A -0.1(7) . . . . ?
C16B C12B C13B C14B 0 . . . . ?
C17 C12B C13B C14B 178.9(5) . . . . ?
C12B C13B C14B N4B 0 . . . . ?
C13B C14B N4B C15B 0 . . . . ?
C14B N4B C15B C16B 0 . . . . ?
N4B C15B C16B C12B 0 . . . . ?
C13B C12B C16B C15B 0 . . . . ?
C17 C12B C16B C15B -178.9(5) . . . . ?
C8 C9 N2B N3B 167(3) . . . . ?
C10 C9 N2B N3B -12(4) . . . . ?

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
O1 H1 N1 0.82 1.95 2.7619(14) 174.1 1_556 yes
O2 H2A N4A 0.82 2.06 2.871(9) 172.4 2_666 yes
O2 H2A N4B 0.82 1.92 2.74(2) 178.1 2_666 yes

####################################################################### 
# 
# 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_A75_BE25_210
_database_code_depnum_ccdc_archive 'CCDC 1995489'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT041_A75_BE25_210        
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)ethylene molecules within the structure. At this  
          temperature the free variable for the site occupancies of the 
          disordered nitrogen and carbon atoms would not fully converge. 
;
# end Validation Reply Form

_audit_creation_date             2020-03-12T16:23:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C16.59 H14.59 N3.41 O2'
_chemical_formula_weight         293.73

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9687(2)
_cell_length_b                   9.7664(2)
_cell_length_c                   10.8474(2)
_cell_angle_alpha                93.6260(17)
_cell_angle_beta                 106.527(2)
_cell_angle_gamma                113.856(2)
_cell_volume                     724.71(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    14876
_cell_measurement_theta_min      4.302
_cell_measurement_theta_max      76.711

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.056
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             308
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 6 -1 0.055
0 4 4 0.0525
0 -6 2 0.0757
3 -6 0 0.0674
5 -1 0 0.0887
5 0 -3 0.0947
0 0 7 0.026
0 0 -7 0.0283
-2 -3 -2 0.0761
-5 0 3 0.0919


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.659
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.854
_shelx_estimated_absorpt_T_max   0.959

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      210(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0286176
_diffrn_orient_matrix_ub_12      -0.1659892
_diffrn_orient_matrix_ub_13      -0.0022722
_diffrn_orient_matrix_ub_21      -0.1030492
_diffrn_orient_matrix_ub_22      -0.0394921
_diffrn_orient_matrix_ub_23      -0.1499495
_diffrn_orient_matrix_ub_31      0.1976735
_diffrn_orient_matrix_ub_32      0.0438129
_diffrn_orient_matrix_ub_33      -0.0200628
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_number            27317
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.342
_diffrn_reflns_theta_max         77.219
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_reflns_Friedel_coverage         0
_reflns_number_total             2988
_reflns_number_gt                2703
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0622P)²+0.1035P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0047(9)
_refine_ls_number_reflns         2988
_refine_ls_number_parameters     242
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.042
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1117
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)ethylene and the pedal motion about the azo group, the atom 
 sites N2 and N3, were split into parts A and B. These sites were allowed to 
 free refine their site occupancies to a total value of 1. To help maintain 
 reasonable ADP and bond lengths, SIMU, RIGU, and DFIX restraints and 
 constraints were applied. At this temperature the ratio of 4,4'-azopyridine 
 to bis(4-pyridyl)ethylene was 0.76 to 0.24 with the amount of 
 4,4'-azopyridine in the secondary position calculated at 0.03. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16492(12) 0.16133(10) 0.31161(8) 0.0444(2) Uani 1 1 d . . . . .
H1 H 0.197213 0.187151 0.392392 0.067 Uiso 1 1 calc R U . . .
O2 O 0.82413(13) 0.22402(11) 0.43440(8) 0.0516(3) Uani 1 1 d . . . . .
H2A H 0.829046 0.263434 0.506204 0.077 Uiso 1 1 calc R U . . .
N1 N 0.26075(15) 0.24927(12) 0.57928(10) 0.0445(3) Uani 1 1 d . . . . .
N2A N 0.2133(16) 0.3754(7) 0.9437(7) 0.0382(9) Uani 0.723(3) 1 d D U P A 1
N3A N 0.2683(10) 0.5143(6) 0.9814(4) 0.0368(6) Uani 0.723(3) 1 d D U P A 1
C17 C 0.213(6) 0.383(2) 0.937(3) 0.039(2) Uani 0.243(3) 1 d D U P A 2
H17 H 0.150579 0.30118 0.97482 0.047 Uiso 0.243(3) 1 calc R U P A 2
C18 C 0.263(4) 0.521(2) 0.9995(14) 0.0367(19) Uani 0.243(3) 1 d D U P A 2
H18 H 0.326532 0.603621 0.963343 0.044 Uiso 0.243(3) 1 calc DR U P A 2
N2B N 0.286(5) 0.477(4) 0.932(3) 0.041(3) Uani 0.034(2) 1 d D U P A 3
N3B N 0.186(4) 0.404(4) 0.996(3) 0.042(3) Uani 0.034(2) 1 d D U P A 3
N4 N 0.17550(14) 0.65025(11) 1.32807(9) 0.0425(2) Uani 1 1 d . . . . .
C1 C 0.31682(17) 0.15645(12) 0.28143(11) 0.0369(3) Uani 1 1 d . . . . .
C2 C 0.49365(17) 0.19092(12) 0.37764(10) 0.0377(3) Uani 1 1 d . . . . .
H2 H 0.509802 0.217151 0.466543 0.045 Uiso 1 1 calc R U . . .
C3 C 0.64751(17) 0.18688(12) 0.34325(11) 0.0394(3) Uani 1 1 d . . . . .
C4 C 0.62221(19) 0.14460(13) 0.21165(12) 0.0444(3) Uani 1 1 d . . . . .
H4 H 0.724165 0.139412 0.187537 0.053 Uiso 1 1 calc R U . . .
C5 C 0.4450(2) 0.11045(13) 0.11729(11) 0.0457(3) Uani 1 1 d . . . . .
H5 H 0.428164 0.082791 0.028461 0.055 Uiso 1 1 calc R U . . .
C6 C 0.29143(19) 0.11573(13) 0.14961(11) 0.0435(3) Uani 1 1 d . . . . .
H6 H 0.172074 0.092258 0.083781 0.052 Uiso 1 1 calc R U . . .
C7 C 0.32370(18) 0.39730(14) 0.62954(12) 0.0461(3) Uani 1 1 d . . . . .
H7 H 0.373756 0.469724 0.580426 0.055 Uiso 1 1 calc R U . . .
C8 C 0.31923(18) 0.44942(14) 0.74914(12) 0.0434(3) Uani 1 1 d . . . . .
H8 H 0.366885 0.554511 0.781367 0.052 Uiso 1 1 calc DR U . . .
C9 C 0.24216(16) 0.34200(13) 0.82071(11) 0.0374(3) Uani 1 1 d D . . . .
C10 C 0.18019(18) 0.18889(14) 0.77110(12) 0.0427(3) Uani 1 1 d . . . . .
H10 H 0.130473 0.113982 0.818367 0.051 Uiso 1 1 calc R U . . .
C11 C 0.19276(18) 0.14839(14) 0.65117(12) 0.0446(3) Uani 1 1 d . . . . .
H11 H 0.1513 0.044372 0.618392 0.053 Uiso 1 1 calc R U . . .
C12 C 0.23214(16) 0.55308(13) 1.10292(11) 0.0381(3) Uani 1 1 d D . . . .
C13 C 0.28780(18) 0.70584(14) 1.14686(12) 0.0448(3) Uani 1 1 d . . . . .
H13 H 0.345552 0.779395 1.100983 0.054 Uiso 1 1 calc R U . . .
C14 C 0.25751(18) 0.74898(14) 1.25890(12) 0.0463(3) Uani 1 1 d . . . . .
H14 H 0.296651 0.85341 1.288153 0.056 Uiso 1 1 calc R U . . .
C15 C 0.12061(17) 0.50177(14) 1.28468(12) 0.0424(3) Uani 1 1 d . . . . .
H15 H 0.062067 0.430742 1.332119 0.051 Uiso 1 1 calc R U . . .
C16 C 0.14591(18) 0.44808(13) 1.17361(12) 0.0421(3) Uani 1 1 d . . . . .
H16 H 0.105838 0.343102 1.14639 0.051 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3583(14) . ?
O1 H1 0.83 . ?
O2 C3 1.3564(14) . ?
O2 H2A 0.83 . ?
N1 C11 1.3335(16) . ?
N1 C7 1.3405(16) . ?
N2A N3A 1.244(4) . ?
N2A C9 1.456(5) . ?
N3A C12 1.484(3) . ?
C17 C18 1.322(10) . ?
C17 C9 1.408(18) . ?
C17 H17 0.94 . ?
C18 C12 1.260(9) . ?
C18 H18 0.94 . ?
N2B N3B 1.242(10) . ?
N2B C9 1.58(4) . ?
N3B C12 1.65(4) . ?
N4 C14 1.3344(16) . ?
N4 C15 1.3413(15) . ?
C1 C2 1.3868(16) . ?
C1 C6 1.3936(15) . ?
C2 C3 1.3934(16) . ?
C2 H2 0.94 . ?
C3 C4 1.3940(16) . ?
C4 C5 1.3807(18) . ?
C4 H4 0.94 . ?
C5 C6 1.3843(18) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3788(17) . ?
C7 H7 0.94 . ?
C8 C9 1.3905(17) . ?
C8 H8 0.94 . ?
C9 C10 1.3853(16) . ?
C10 C11 1.3785(16) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.3799(17) . ?
C12 C16 1.3931(17) . ?
C13 C14 1.3774(17) . ?
C13 H13 0.94 . ?
C14 H14 0.94 . ?
C15 C16 1.3824(16) . ?
C15 H15 0.94 . ?
C16 H16 0.94 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 117.27(10) . . ?
N3A N2A C9 112.5(5) . . ?
N2A N3A C12 114.5(4) . . ?
C18 C17 C9 127.8(18) . . ?
C18 C17 H17 116.1 . . ?
C9 C17 H17 116.1 . . ?
C12 C18 C17 126.1(17) . . ?
C12 C18 H18 117 . . ?
C17 C18 H18 117 . . ?
N3B N2B C9 100(3) . . ?
N2B N3B C12 96(3) . . ?
C14 N4 C15 117.38(10) . . ?
O1 C1 C2 121.79(9) . . ?
O1 C1 C6 118.18(10) . . ?
C2 C1 C6 120.03(11) . . ?
C1 C2 C3 120.36(10) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 121.96(10) . . ?
O2 C3 C4 118.20(11) . . ?
C2 C3 C4 119.84(11) . . ?
C5 C4 C3 118.95(11) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.96(10) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.85(11) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C8 123.76(11) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.06(11) . . ?
C7 C8 H8 121 . . ?
C9 C8 H8 121 . . ?
C10 C9 C8 118.74(11) . . ?
C10 C9 C17 118.9(10) . . ?
C8 C9 C17 122.2(10) . . ?
C10 C9 N2A 115.8(3) . . ?
C8 C9 N2A 125.5(3) . . ?
C10 C9 N2B 152.1(10) . . ?
C8 C9 N2B 89.1(10) . . ?
C11 C10 C9 118.79(11) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.34(11) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C18 C12 C13 115.9(10) . . ?
C18 C12 C16 125.7(10) . . ?
C13 C12 C16 118.44(11) . . ?
C13 C12 N3A 116.3(2) . . ?
C16 C12 N3A 125.2(2) . . ?
C13 C12 N3B 154.8(9) . . ?
C16 C12 N3B 86.2(9) . . ?
C14 C13 C12 119.05(11) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
N4 C14 C13 123.41(11) . . ?
N4 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
N4 C15 C16 123.21(11) . . ?
N4 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C15 C16 C12 118.50(11) . . ?
C15 C16 H16 120.7 . . ?
C12 C16 H16 120.7 . . ?

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
O1 H1 N1 0.83 1.94 2.7647(13) 177 . yes
O2 H2A N4 0.83 1.95 2.7820(13) 176.7 2_667 yes

####################################################################### 
# 
# 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_A25_BA75_210
_database_code_depnum_ccdc_archive 'CCDC 1995551'
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;


# start Validation Reply Form
_vrf_PLAT077_A25_BA75_210        
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)acetylene molecules.
;
_vrf_PLAT911_A25_BA75_210        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         17 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2020-02-26T14:17:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C17.35 H14 N2.65 O2'
_chemical_formula_weight         291.61

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.14555(15)
_cell_length_b                   9.77001(17)
_cell_length_c                   10.9352(2)
_cell_angle_alpha                92.2730(14)
_cell_angle_beta                 107.9416(16)
_cell_angle_gamma                114.4897(17)
_cell_volume                     739.23(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    15436
_cell_measurement_theta_min      4.32
_cell_measurement_theta_max      76.589

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.103
_exptl_crystal_density_diffrn    1.31
_exptl_crystal_F_000             305
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -1 0 0.0411
-3 5 4 0.0981
-1 -3 7 0.0767
1 3 -7 0.0786
2 -1 -7 0.0773
4 1 0 0.0599
2 -6 2 0.0625
0 -5 -2 0.0599
4 -1 -6 0.0847
3 -4 4 0.0491
-5 2 4 0.0882
1 -6 -1 0.0572
0 6 -2 0.0472
-2 6 -2 0.0453
1 -5 5 0.0477


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.572
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.871
_shelx_estimated_absorpt_T_max   0.93

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      210(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.1814975
_diffrn_orient_matrix_ub_12      -0.1495736
_diffrn_orient_matrix_ub_13      -0.0768404
_diffrn_orient_matrix_ub_21      -0.1286293
_diffrn_orient_matrix_ub_22      0.0726644
_diffrn_orient_matrix_ub_23      0.0180122
_diffrn_orient_matrix_ub_31      -0.0027413
_diffrn_orient_matrix_ub_32      0.0594625
_diffrn_orient_matrix_ub_33      -0.1286498
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_number            23128
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.331
_diffrn_reflns_theta_max         77.376
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.948
_reflns_Friedel_coverage         0
_reflns_number_total             2982
_reflns_number_gt                2577
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0583P)²+0.0890P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0045(9)
_refine_ls_number_reflns         2982
_refine_ls_number_parameters     284
_refine_ls_number_restraints     513
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      0.99
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.034

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)acetylene and the pedal motion about the azo group and pyridyl
 rings, the atom sites N2 < N4 and C12 < C16, were split into parts A and B.
 These sites were allowed to free refine their site occupancies to a total 
 value of 1. To help maintain reasonable ADP and bond lengths, SIMU, RIGU, and 
 DFIX restraints and constraints were applied. At this temperature the ratio of 
 4,4'-azopyridine to bis(4-pyridyl)acetylene was 0.31 to 0.67 with the amount 
 of 4,4'-azopyridine in the secondary position calculated at 0.02. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16718(12) 0.14811(10) 0.30699(8) 0.0515(2) Uani 1 1 d . . . . .
H1 H 0.200929 0.175193 0.387276 0.077 Uiso 1 1 calc R U . . .
O2 O 0.81752(13) 0.21143(11) 0.43458(9) 0.0588(3) Uani 1 1 d . . . . .
H2A H 0.825773 0.252679 0.505494 0.088 Uiso 1 1 calc R U . . .
N1 N 0.26267(15) 0.24347(13) -0.42961(10) 0.0530(3) Uani 1 1 d . . . . .
C1 C 0.31752(16) 0.14766(12) 0.27825(11) 0.0426(3) Uani 1 1 d . . . . .
C2 C 0.49163(16) 0.17833(12) 0.37551(11) 0.0432(3) Uani 1 1 d . . . . .
H2 H 0.507087 0.199491 0.464058 0.052 Uiso 1 1 calc R U . . .
C3 C 0.64350(17) 0.17794(13) 0.34266(12) 0.0459(3) Uani 1 1 d . . . . .
C4 C 0.6192(2) 0.14277(14) 0.21170(13) 0.0537(3) Uani 1 1 d . . . . .
H4 H 0.71984 0.139682 0.188629 0.064 Uiso 1 1 calc R U . . .
C5 C 0.4449(2) 0.11248(15) 0.11625(12) 0.0561(3) Uani 1 1 d . . . . .
H5 H 0.428658 0.089534 0.027752 0.067 Uiso 1 1 calc R U . . .
C6 C 0.29367(19) 0.11492(14) 0.14702(12) 0.0513(3) Uani 1 1 d . . . . .
H6 H 0.176601 0.094816 0.080441 0.062 Uiso 1 1 calc R U . . .
C7 C 0.32975(19) 0.39322(16) -0.38645(14) 0.0562(3) Uani 1 1 d . . . . .
H7 H 0.377964 0.461775 -0.438943 0.067 Uiso 1 1 calc R U . . .
C8 C 0.33206(18) 0.45243(14) -0.26951(14) 0.0536(3) Uani 1 1 d . . . . .
H8 H 0.382797 0.558831 -0.24224 0.064 Uiso 1 1 calc R U . . .
C9 C 0.25783(16) 0.35176(13) -0.19239(12) 0.0452(3) Uani 1 1 d D . . . .
C10 C 0.18981(17) 0.19553(13) -0.23544(12) 0.0476(3) Uani 1 1 d . . . . .
H10 H 0.140536 0.124158 -0.185185 0.057 Uiso 1 1 calc R U . . .
C11 C 0.19642(18) 0.14800(14) -0.35338(12) 0.0501(3) Uani 1 1 d . . . . .
H11 H 0.151813 0.042577 -0.381626 0.06 Uiso 1 1 calc R U . . .
N2A N 0.2217(16) 0.3814(10) -0.0623(10) 0.0481(17) Uani 0.308(3) 1 d D U P A 1
N3A N 0.2605(9) 0.5062(7) -0.0135(7) 0.0532(13) Uani 0.308(3) 1 d D U P A 1
C12A C 0.2292(18) 0.5526(12) 0.1034(10) 0.0414(14) Uani 0.308(3) 1 d . U P A 1
C13A C 0.282(2) 0.7044(12) 0.1548(11) 0.0475(18) Uani 0.308(3) 1 d . U P A 1
H13A H 0.340552 0.785841 0.115382 0.057 Uiso 0.308(3) 1 calc R U P A 1
C14A C 0.245(2) 0.7285(10) 0.2678(12) 0.0431(15) Uani 0.308(3) 1 d . U P A 1
H14A H 0.281392 0.831436 0.300427 0.052 Uiso 0.308(3) 1 calc R U P A 1
N4A N 0.1721(19) 0.6384(11) 0.3302(11) 0.0485(17) Uani 0.308(3) 1 d . U P A 1
C15A C 0.1227(15) 0.5034(10) 0.2801(9) 0.0456(16) Uani 0.308(3) 1 d . U P A 1
H15A H 0.061545 0.427993 0.323344 0.055 Uiso 0.308(3) 1 calc R U P A 1
C16A C 0.1446(15) 0.4488(9) 0.1708(9) 0.0466(17) Uani 0.308(3) 1 d . U P A 1
H16A H 0.1023 0.343499 0.143954 0.056 Uiso 0.308(3) 1 calc R U P A 1
C12B C 0.2118(7) 0.5267(4) 0.1252(3) 0.0387(9) Uani 0.692(3) 1 d DG U P A 2
C13B C 0.2796(8) 0.6848(4) 0.1500(4) 0.0471(10) Uani 0.692(3) 1 d G U P A 2
H13B H 0.339115 0.744325 0.096444 0.057 Uiso 0.692(3) 1 calc R U P A 2
C14B C 0.2596(9) 0.7549(3) 0.2539(5) 0.0453(9) Uani 0.692(3) 1 d G U P A 2
H14B H 0.305444 0.861803 0.270602 0.054 Uiso 0.692(3) 1 calc R U P A 2
N4B N 0.1716(8) 0.6668(4) 0.3330(4) 0.0456(8) Uani 0.692(3) 1 d G U P A 2
C15B C 0.1038(6) 0.5087(4) 0.3083(3) 0.0461(8) Uani 0.692(3) 1 d G U P A 2
H15B H 0.044307 0.449177 0.361778 0.055 Uiso 0.692(3) 1 calc R U P A 2
C16B C 0.1239(6) 0.4386(3) 0.2044(3) 0.0430(8) Uani 0.692(3) 1 d G U P A 2
H16B H 0.077976 0.331696 0.18762 0.052 Uiso 0.692(3) 1 calc R U P A 2
C17 C 0.2326(5) 0.4600(4) 0.0168(3) 0.0419(7) Uani 0.674(3) 1 d D U P A 2
C18 C 0.2523(8) 0.4149(6) -0.0791(5) 0.0438(9) Uani 0.674(3) 1 d D U P A 2
N2B N 0.294(10) 0.480(10) -0.064(10) 0.048(4) Uani 0.018(2) 1 d D U P A 3
N3B N 0.154(9) 0.394(9) -0.036(8) 0.046(6) Uani 0.018(2) 1 d D U P A 3



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3565(14) . ?
O1 H1 0.83 . ?
O2 C3 1.3558(15) . ?
O2 H2A 0.83 . ?
N1 C11 1.3334(17) . ?
N1 C7 1.3362(17) . ?
C1 C2 1.3876(16) . ?
C1 C6 1.3927(16) . ?
C2 C3 1.3918(16) . ?
C2 H2 0.94 . ?
C3 C4 1.3921(17) . ?
C4 C5 1.3809(19) . ?
C4 H4 0.94 . ?
C5 C6 1.3823(19) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3739(19) . ?
C7 H7 0.94 . ?
C8 C9 1.3896(19) . ?
C8 H8 0.94 . ?
C9 C18 1.384(6) . ?
C9 C10 1.3927(16) . ?
C9 N2A 1.578(10) . ?
C9 N2B 1.71(11) . ?
C10 C11 1.3775(17) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
N2A N3A 1.181(12) . ?
N3A C12A 1.469(12) . ?
C12A C16A 1.355(9) . ?
C12A C13A 1.398(8) . ?
C13A C14A 1.396(8) . ?
C13A H13A 0.94 . ?
C14A N4A 1.206(9) . ?
C14A C15A 2.034(10) . ?
C14A H14A 0.94 . ?
N4A C15A 1.252(9) . ?
C15A C16A 1.380(9) . ?
C15A H15A 0.94 . ?
C16A H16A 0.94 . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
C12B C17 1.418(4) . ?
C13B C14B 1.39 . ?
C13B H13B 0.94 . ?
C14B N4B 1.39 . ?
C14B H14B 0.94 . ?
N4B C15B 1.39 . ?
C15B C16B 1.39 . ?
C15B H15B 0.94 . ?
C16B H16B 0.94 . ?
C17 C18 1.203(7) . ?
N2B N3B 1.25(2) . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 117.41(11) . . ?
O1 C1 C2 121.80(10) . . ?
O1 C1 C6 118.27(11) . . ?
C2 C1 C6 119.93(11) . . ?
C1 C2 C3 120.35(11) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.16(11) . . ?
O2 C3 C4 117.95(11) . . ?
C2 C3 C4 119.90(11) . . ?
C5 C4 C3 118.92(12) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.94(11) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.93(12) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.56(12) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 118.62(12) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C18 C9 C8 117.0(2) . . ?
C18 C9 C10 124.6(2) . . ?
C8 C9 C10 118.38(11) . . ?
C8 C9 N2A 130.8(3) . . ?
C10 C9 N2A 110.7(3) . . ?
C8 C9 N2B 100(2) . . ?
C10 C9 N2B 142(2) . . ?
C11 C10 C9 118.47(12) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
N1 C11 C10 123.53(11) . . ?
N1 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
N3A N2A C9 121.2(9) . . ?
N2A N3A C12A 128.0(10) . . ?
C16A C12A C13A 114.4(6) . . ?
C16A C12A N3A 121.8(7) . . ?
C13A C12A N3A 123.8(8) . . ?
C14A C13A C12A 116.4(6) . . ?
C14A C13A H13A 121.8 . . ?
C12A C13A H13A 121.8 . . ?
N4A C14A C13A 130.3(6) . . ?
N4A C14A C15A 34.9(4) . . ?
C13A C14A C15A 95.4(5) . . ?
N4A C14A H14A 114.9 . . ?
C13A C14A H14A 114.9 . . ?
C15A C14A H14A 149.7 . . ?
C14A N4A C15A 111.7(6) . . ?
N4A C15A C16A 129.7(6) . . ?
N4A C15A C14A 33.4(3) . . ?
C16A C15A C14A 96.2(5) . . ?
N4A C15A H15A 115.2 . . ?
C16A C15A H15A 115.2 . . ?
C14A C15A H15A 148.6 . . ?
C12A C16A C15A 117.6(5) . . ?
C12A C16A H16A 121.2 . . ?
C15A C16A H16A 121.2 . . ?
C13B C12B C16B 120 . . ?
C13B C12B C17 118.0(2) . . ?
C16B C12B C17 122.0(2) . . ?
C12B C13B C14B 120 . . ?
C12B C13B H13B 120 . . ?
C14B C13B H13B 120 . . ?
N4B C14B C13B 120 . . ?
N4B C14B H14B 120 . . ?
C13B C14B H14B 120 . . ?
C15B N4B C14B 120 . . ?
N4B C15B C16B 120 . . ?
N4B C15B H15B 120 . . ?
C16B C15B H15B 120 . . ?
C15B C16B C12B 120 . . ?
C15B C16B H16B 120 . . ?
C12B C16B H16B 120 . . ?
C18 C17 C12B 174.4(4) . . ?
C17 C18 C9 174.6(5) . . ?
N3B N2B C9 96(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -179.57(10) . . . . ?
C6 C1 C2 C3 0.57(17) . . . . ?
C1 C2 C3 O2 178.16(10) . . . . ?
C1 C2 C3 C4 -1.65(17) . . . . ?
O2 C3 C4 C5 -178.21(11) . . . . ?
C2 C3 C4 C5 1.60(18) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C4 C5 C6 C1 -0.55(19) . . . . ?
O1 C1 C6 C5 -179.34(11) . . . . ?
C2 C1 C6 C5 0.52(17) . . . . ?
C11 N1 C7 C8 -0.58(19) . . . . ?
N1 C7 C8 C9 -1.16(19) . . . . ?
C7 C8 C9 C18 -176.4(3) . . . . ?
C7 C8 C9 C10 1.93(18) . . . . ?
C7 C8 C9 N2A -173.4(6) . . . . ?
C7 C8 C9 N2B -180(3) . . . . ?
C18 C9 C10 C11 177.1(3) . . . . ?
C8 C9 C10 C11 -1.04(17) . . . . ?
N2A C9 C10 C11 175.2(5) . . . . ?
N2B C9 C10 C11 -178(4) . . . . ?
C7 N1 C11 C10 1.56(18) . . . . ?
C9 C10 C11 N1 -0.74(18) . . . . ?
C8 C9 N2A N3A -0.6(14) . . . . ?
C10 C9 N2A N3A -176.2(9) . . . . ?
C9 N2A N3A C12A 177.3(8) . . . . ?
N2A N3A C12A C16A -0.8(16) . . . . ?
N2A N3A C12A C13A 179.2(11) . . . . ?
C16A C12A C13A C14A 0.9(7) . . . . ?
N3A C12A C13A C14A -179.1(11) . . . . ?
C12A C13A C14A N4A 0.1(8) . . . . ?
C12A C13A C14A C15A -0.7(5) . . . . ?
C13A C14A N4A C15A -1.4(8) . . . . ?
C14A N4A C15A C16A 1.9(8) . . . . ?
C13A C12A C16A C15A -0.6(7) . . . . ?
N3A C12A C16A C15A 179.5(10) . . . . ?
N4A C15A C16A C12A -1.0(9) . . . . ?
C14A C15A C16A C12A 0.1(5) . . . . ?
C16B C12B C13B C14B 0 . . . . ?
C17 C12B C13B C14B 179.0(4) . . . . ?
C12B C13B C14B N4B 0 . . . . ?
C13B C14B N4B C15B 0 . . . . ?
C14B N4B C15B C16B 0 . . . . ?
N4B C15B C16B C12B 0 . . . . ?
C13B C12B C16B C15B 0 . . . . ?
C17 C12B C16B C15B -178.9(5) . . . . ?
C8 C9 N2B N3B 150(5) . . . . ?
C10 C9 N2B N3B -33(8) . . . . ?

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
O1 H1 N1 0.83 1.92 2.7523(13) 175.2 1_556 yes
O2 H2A N4A 0.83 2.04 2.871(9) 174.4 2_666 yes
O2 H2A N4B 0.83 1.89 2.72(2) 175.7 2_666 yes

####################################################################### 
# 
# 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_A25_BA75_190
_database_code_depnum_ccdc_archive 'CCDC 1995550'
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT077__A25_BA75_190       
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)acetylene molecules.
;
_vrf_PLAT911__A25_BA75_190       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         15 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2020-02-26T14:11:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C17.35 H14 N2.65 O2'
_chemical_formula_weight         291.6

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.13293(19)
_cell_length_b                   9.7619(2)
_cell_length_c                   10.9275(3)
_cell_angle_alpha                92.167(2)
_cell_angle_beta                 107.990(2)
_cell_angle_gamma                114.537(2)
_cell_volume                     736.68(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    15946
_cell_measurement_theta_min      4.323
_cell_measurement_theta_max      75.822

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.103
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             305
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -1 0 0.0411
4 1 0 0.0599
1 3 -7 0.0786
-1 -3 7 0.0767
-2 6 -2 0.0453
1 -5 5 0.0477
2 -1 -7 0.0773
2 -6 2 0.0625
-3 5 4 0.0981
4 -1 -6 0.0847
3 -4 4 0.0491
-5 2 4 0.0882
0 6 -2 0.0472
1 -6 -1 0.0572
0 -5 -2 0.0599


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.483
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.87
_shelx_estimated_absorpt_T_max   0.93

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      190(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.1817484
_diffrn_orient_matrix_ub_12      -0.1496038
_diffrn_orient_matrix_ub_13      -0.0772361
_diffrn_orient_matrix_ub_21      -0.1290572
_diffrn_orient_matrix_ub_22      0.0725782
_diffrn_orient_matrix_ub_23      0.0176603
_diffrn_orient_matrix_ub_31      -0.0020375
_diffrn_orient_matrix_ub_32      0.0599772
_diffrn_orient_matrix_ub_33      -0.1285853
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_number            23395
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.334
_diffrn_reflns_theta_max         77.324
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.949
_reflns_Friedel_coverage         0
_reflns_number_total             2980
_reflns_number_gt                2626
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom


#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0577P)²+0.0874P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0046(9)
_refine_ls_number_reflns         2980
_refine_ls_number_parameters     284
_refine_ls_number_restraints     507
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1091
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.034

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)acetylene and the pedal motion about the azo group and pyridyl
 rings, the atom sites N2 < N4 and C12 < C16, were split into parts A and B.
 These sites were allowed to free refine their site occupancies to a total 
 value of 1. To help maintain reasonable ADP and bond lengths, SIMU, RIGU, and 
 DFIX restraints and constraints were applied. At this temperature the ratio of 
 4,4'-azopyridine to bis(4-pyridyl)acetylene was 0.31 to 0.68 with the amount 
 of 4,4'-azopyridine in the secondary position calculated at 0.01. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16650(11) 0.14843(10) 0.30695(8) 0.0475(2) Uani 1 1 d . . . . .
H1 H 0.200006 0.17404 0.388393 0.071 Uiso 1 1 calc R U . . .
O2 O 0.81807(12) 0.21111(11) 0.43496(9) 0.0540(3) Uani 1 1 d . . . . .
H2A H 0.826473 0.252912 0.506716 0.081 Uiso 1 1 calc R U . . .
N1 N 0.26268(14) 0.24379(12) -0.42975(10) 0.0496(3) Uani 1 1 d . . . . .
C1 C 0.31728(16) 0.14796(12) 0.27828(11) 0.0398(3) Uani 1 1 d . . . . .
C2 C 0.49162(16) 0.17847(12) 0.37580(11) 0.0402(3) Uani 1 1 d . . . . .
H2 H 0.507284 0.199814 0.465336 0.048 Uiso 1 1 calc R U . . .
C3 C 0.64379(17) 0.17791(12) 0.34279(11) 0.0428(3) Uani 1 1 d . . . . .
C4 C 0.61911(19) 0.14258(14) 0.21169(12) 0.0496(3) Uani 1 1 d . . . . .
H4 H 0.720851 0.139284 0.188361 0.06 Uiso 1 1 calc R U . . .
C5 C 0.4446(2) 0.11243(14) 0.11613(12) 0.0520(3) Uani 1 1 d . . . . .
H5 H 0.427966 0.089104 0.02663 0.062 Uiso 1 1 calc R U . . .
C6 C 0.29329(18) 0.11522(13) 0.14704(12) 0.0478(3) Uani 1 1 d . . . . .
H6 H 0.174785 0.095095 0.079721 0.057 Uiso 1 1 calc R U . . .
C7 C 0.33000(18) 0.39367(15) -0.38638(13) 0.0522(3) Uani 1 1 d . . . . .
H7 H 0.379064 0.463254 -0.439316 0.063 Uiso 1 1 calc R U . . .
C8 C 0.33208(18) 0.45261(14) -0.26928(13) 0.0503(3) Uani 1 1 d . . . . .
H8 H 0.383195 0.560183 -0.241701 0.06 Uiso 1 1 calc R U . . .
C9 C 0.25792(16) 0.35159(13) -0.19221(11) 0.0424(3) Uani 1 1 d D . . . .
C10 C 0.18981(17) 0.19523(13) -0.23518(12) 0.0439(3) Uani 1 1 d . . . . .
H10 H 0.139956 0.122923 -0.184327 0.053 Uiso 1 1 calc R U . . .
C11 C 0.19649(17) 0.14788(14) -0.35330(12) 0.0463(3) Uani 1 1 d . . . . .
H11 H 0.151574 0.041303 -0.381814 0.056 Uiso 1 1 calc R U . . .
N2A N 0.2199(15) 0.3819(9) -0.0612(10) 0.0456(17) Uani 0.311(3) 1 d D U P A 1
N3A N 0.2616(8) 0.5069(6) -0.0146(6) 0.0505(12) Uani 0.311(3) 1 d D U P A 1
C12A C 0.2275(17) 0.5514(12) 0.1015(9) 0.0390(14) Uani 0.311(3) 1 d . U P A 1
C13A C 0.2801(19) 0.7043(12) 0.1525(11) 0.0454(18) Uani 0.311(3) 1 d . U P A 1
H13A H 0.337778 0.786381 0.111879 0.054 Uiso 0.311(3) 1 calc R U P A 1
C14A C 0.243(2) 0.7291(10) 0.2654(12) 0.0398(15) Uani 0.311(3) 1 d . U P A 1
H14A H 0.280806 0.833237 0.298087 0.048 Uiso 0.311(3) 1 calc R U P A 1
N4A N 0.1712(18) 0.6388(11) 0.3286(10) 0.0441(15) Uani 0.311(3) 1 d . U P A 1
C15A C 0.1211(13) 0.5026(10) 0.2790(9) 0.0421(15) Uani 0.311(3) 1 d . U P A 1
H15A H 0.059452 0.426607 0.323179 0.051 Uiso 0.311(3) 1 calc R U P A 1
C16A C 0.1429(14) 0.4476(9) 0.1695(8) 0.0429(16) Uani 0.311(3) 1 d . U P A 1
H16A H 0.100209 0.341049 0.142758 0.051 Uiso 0.311(3) 1 calc R U P A 1
C12B C 0.2127(7) 0.5274(4) 0.1259(3) 0.0355(9) Uani 0.689(3) 1 d DG U P A 2
C13B C 0.2809(8) 0.6857(4) 0.1508(4) 0.0428(9) Uani 0.689(3) 1 d G U P A 2
H13B H 0.341543 0.746141 0.096892 0.051 Uiso 0.689(3) 1 calc R U P A 2
C14B C 0.2604(9) 0.7556(3) 0.2546(5) 0.0420(9) Uani 0.689(3) 1 d G U P A 2
H14B H 0.307054 0.863779 0.27162 0.05 Uiso 0.689(3) 1 calc R U P A 2
N4B N 0.1717(8) 0.6672(4) 0.3335(4) 0.0424(8) Uani 0.689(3) 1 d G U P A 2
C15B C 0.1034(6) 0.5089(4) 0.3086(3) 0.0420(8) Uani 0.689(3) 1 d G U P A 2
H15B H 0.042806 0.448512 0.362537 0.05 Uiso 0.689(3) 1 calc R U P A 2
C16B C 0.1239(5) 0.4390(3) 0.2048(3) 0.0389(7) Uani 0.689(3) 1 d G U P A 2
H16B H 0.077293 0.33087 0.18781 0.047 Uiso 0.689(3) 1 calc R U P A 2
C17 C 0.2327(4) 0.4607(3) 0.0169(3) 0.0382(6) Uani 0.677(3) 1 d D U P A 2
C18 C 0.2526(7) 0.4137(6) -0.0786(5) 0.0409(9) Uani 0.677(3) 1 d D U P A 2
N2B N 0.277(15) 0.455(13) -0.103(12) 0.045(3) Uani 0.013(2) 1 d D U P A 3
N3B N 0.145(13) 0.406(10) -0.057(10) 0.045(6) Uani 0.013(2) 1 d D U P A 3



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3579(14) . ?
O1 H1 0.84 . ?
O2 C3 1.3566(14) . ?
O2 H2A 0.84 . ?
N1 C11 1.3351(17) . ?
N1 C7 1.3369(16) . ?
C1 C2 1.3881(16) . ?
C1 C6 1.3920(16) . ?
C2 C3 1.3940(16) . ?
C2 H2 0.95 . ?
C3 C4 1.3925(17) . ?
C4 C5 1.3805(19) . ?
C4 H4 0.95 . ?
C5 C6 1.3832(18) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.3753(19) . ?
C7 H7 0.95 . ?
C8 C9 1.3886(18) . ?
C8 H8 0.95 . ?
C9 N2B 1.31(11) . ?
C9 C18 1.381(5) . ?
C9 C10 1.3929(16) . ?
C9 N2A 1.597(9) . ?
C10 C11 1.3790(16) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
N2A N3A 1.168(11) . ?
N3A C12A 1.467(10) . ?
C12A C16A 1.359(8) . ?
C12A C13A 1.407(8) . ?
C13A C14A 1.392(8) . ?
C13A H13A 0.95 . ?
C14A N4A 1.210(9) . ?
C14A H14A 0.95 . ?
N4A C15A 1.260(9) . ?
C15A C16A 1.383(8) . ?
C15A H15A 0.95 . ?
C16A H16A 0.95 . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
C12B C17 1.421(4) . ?
C13B C14B 1.39 . ?
C13B H13B 0.95 . ?
C14B N4B 1.39 . ?
C14B H14B 0.95 . ?
N4B C15B 1.39 . ?
C15B C16B 1.39 . ?
C15B H15B 0.95 . ?
C16B H16B 0.95 . ?
C17 C18 1.207(6) . ?
N2B N3B 1.25(2) . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 117.37(11) . . ?
O1 C1 C2 121.75(10) . . ?
O1 C1 C6 118.24(10) . . ?
C2 C1 C6 120.01(11) . . ?
C1 C2 C3 120.22(10) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
O2 C3 C4 118.07(11) . . ?
O2 C3 C2 122.04(10) . . ?
C4 C3 C2 119.89(11) . . ?
C5 C4 C3 119.01(11) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.85(11) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.00(11) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.57(12) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 118.61(11) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
N2B C9 C8 96(4) . . ?
C18 C9 C8 117.2(2) . . ?
N2B C9 C10 145(4) . . ?
C18 C9 C10 124.3(2) . . ?
C8 C9 C10 118.48(11) . . ?
C8 C9 N2A 130.5(3) . . ?
C10 C9 N2A 110.9(3) . . ?
C11 C10 C9 118.41(11) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
N1 C11 C10 123.52(11) . . ?
N1 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
N3A N2A C9 119.8(7) . . ?
N2A N3A C12A 125.9(8) . . ?
C16A C12A C13A 114.3(6) . . ?
C16A C12A N3A 122.5(7) . . ?
C13A C12A N3A 123.2(8) . . ?
C14A C13A C12A 116.6(6) . . ?
C14A C13A H13A 121.7 . . ?
C12A C13A H13A 121.7 . . ?
N4A C14A C13A 130.2(6) . . ?
N4A C14A H14A 114.9 . . ?
C13A C14A H14A 114.9 . . ?
C14A N4A C15A 111.9(6) . . ?
N4A C15A C16A 129.4(6) . . ?
N4A C15A H15A 115.3 . . ?
C16A C15A H15A 115.3 . . ?
C12A C16A C15A 117.6(5) . . ?
C12A C16A H16A 121.2 . . ?
C15A C16A H16A 121.2 . . ?
C13B C12B C16B 120 . . ?
C13B C12B C17 118.0(2) . . ?
C16B C12B C17 122.0(2) . . ?
C14B C13B C12B 120 . . ?
C14B C13B H13B 120 . . ?
C12B C13B H13B 120 . . ?
C13B C14B N4B 120 . . ?
C13B C14B H14B 120 . . ?
N4B C14B H14B 120 . . ?
C14B N4B C15B 120 . . ?
C16B C15B N4B 120 . . ?
C16B C15B H15B 120 . . ?
N4B C15B H15B 120 . . ?
C15B C16B C12B 120 . . ?
C15B C16B H16B 120 . . ?
C12B C16B H16B 120 . . ?
C18 C17 C12B 175.4(4) . . ?
C17 C18 C9 174.9(5) . . ?
N3B N2B C9 112(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -179.63(9) . . . . ?
C6 C1 C2 C3 0.61(16) . . . . ?
C1 C2 C3 O2 178.22(10) . . . . ?
C1 C2 C3 C4 -1.72(17) . . . . ?
O2 C3 C4 C5 -178.30(11) . . . . ?
C2 C3 C4 C5 1.65(17) . . . . ?
C3 C4 C5 C6 -0.49(19) . . . . ?
C4 C5 C6 C1 -0.61(18) . . . . ?
O1 C1 C6 C5 -179.22(10) . . . . ?
C2 C1 C6 C5 0.55(17) . . . . ?
C11 N1 C7 C8 -0.79(18) . . . . ?
N1 C7 C8 C9 -0.98(19) . . . . ?
C7 C8 C9 N2B -175(5) . . . . ?
C7 C8 C9 C18 -176.6(3) . . . . ?
C7 C8 C9 C10 1.84(17) . . . . ?
C7 C8 C9 N2A -172.8(5) . . . . ?
N2B C9 C10 C11 174(9) . . . . ?
C18 C9 C10 C11 177.4(3) . . . . ?
C8 C9 C10 C11 -0.99(17) . . . . ?
N2A C9 C10 C11 174.7(4) . . . . ?
C7 N1 C11 C10 1.73(17) . . . . ?
C9 C10 C11 N1 -0.84(18) . . . . ?
C8 C9 N2A N3A -2.1(13) . . . . ?
C10 C9 N2A N3A -177.1(8) . . . . ?
C9 N2A N3A C12A 177.1(8) . . . . ?
N2A N3A C12A C16A 0.8(15) . . . . ?
N2A N3A C12A C13A -179.6(10) . . . . ?
C16A C12A C13A C14A 1.4(7) . . . . ?
N3A C12A C13A C14A -178.2(10) . . . . ?
C12A C13A C14A N4A -0.3(8) . . . . ?
C13A C14A N4A C15A -1.4(8) . . . . ?
C14A N4A C15A C16A 2.1(8) . . . . ?
C13A C12A C16A C15A -0.8(7) . . . . ?
N3A C12A C16A C15A 178.8(10) . . . . ?
N4A C15A C16A C12A -1.0(8) . . . . ?
C16B C12B C13B C14B 0 . . . . ?
C17 C12B C13B C14B 178.5(4) . . . . ?
C12B C13B C14B N4B 0 . . . . ?
C13B C14B N4B C15B 0 . . . . ?
C14B N4B C15B C16B 0 . . . . ?
N4B C15B C16B C12B 0 . . . . ?
C13B C12B C16B C15B 0 . . . . ?
C17 C12B C16B C15B -178.5(4) . . . . ?
C8 C9 N2B N3B 146(9) . . . . ?
C10 C9 N2B N3B -30(17) . . . . ?

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
O1 H1 N1 0.84 1.91 2.7494(13) 174.5 1_556 yes
O2 H2A N4A 0.84 2.04 2.880(8) 174.7 2_666 yes
O2 H2A N4B 0.84 1.88 2.72(2) 175.6 2_666 yes

####################################################################### 
# 
# 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_A75_BE25_270
_database_code_depnum_ccdc_archive 'CCDC 1995492'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT230_A75_BE25_270        
;
PROBLEM: Hirshfeld Test Diff for    C12      --C16      .        7.2 s.u.  
RESPONSE: Due to the pedal motion of the 4,4'-azopyridine molecule and not
          modeling the disorder about the pyridine rings.
;
_vrf_PLAT077_A75_BE25_270        
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)ethylene molecules within the structure. 
;
_vrf_PLAT906_A75_BE25_270        
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.038 Check 
RESPONSE: This appears to be due to slght movement of the crystal during the
          experiment at this temperature and the removal of a some high 
          angle data during the integration.
;
# end Validation Reply Form

_audit_creation_date             2020-03-12T16:25:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C16.46 H14.46 N3.54 O2'
_chemical_formula_weight         293.85

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.02672(12)
_cell_length_b                   9.79494(16)
_cell_length_c                   10.86753(18)
_cell_angle_alpha                93.9195(13)
_cell_angle_beta                 106.4603(14)
_cell_angle_gamma                113.7186(15)
_cell_volume                     733.83(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    12760
_cell_measurement_theta_min      4.302
_cell_measurement_theta_max      75.488

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.056
_exptl_crystal_density_diffrn    1.33
_exptl_crystal_F_000             308
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 6 -1 0.055
0 4 4 0.0525
0 -6 2 0.0757
3 -6 0 0.0674
5 -1 0 0.0887
5 0 -3 0.0947
0 0 7 0.026
0 0 -7 0.0283
-2 -3 -2 0.0761
-5 0 3 0.0919


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.659
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.855
_shelx_estimated_absorpt_T_max   0.96

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      270(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0287982
_diffrn_orient_matrix_ub_12      -0.1656182
_diffrn_orient_matrix_ub_13      -0.0028696
_diffrn_orient_matrix_ub_21      -0.0997322
_diffrn_orient_matrix_ub_22      -0.0388472
_diffrn_orient_matrix_ub_23      -0.1499918
_diffrn_orient_matrix_ub_31      0.1973026
_diffrn_orient_matrix_ub_32      0.0436369
_diffrn_orient_matrix_ub_33      -0.018127
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_number            27725
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.337
_diffrn_reflns_theta_max         77.344
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.968
_reflns_Friedel_coverage         0
_reflns_number_total             3022
_reflns_number_gt                2606
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0667P)²+0.0966P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0047(10)
_refine_ls_number_reflns         3022
_refine_ls_number_parameters     242
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1254
_refine_ls_wR_factor_gt          0.1206
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.034

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)ethylene and the pedal motion about the azo group, the atom 
 sites N2 and N3, were split into parts A and B. These sites were allowed to 
 free refine their site occupancies to a total value of 1. To help maintain 
 reasonable ADP and bond lengths, SIMU, RIGU, and DFIX restraints and 
 constraints were applied. At this temperature the ratio of 4,4'-azopyridine 
 to bis(4-pyridyl)ethylene was 0.77 to 0.23 with the amount of 
 4,4'-azopyridine in the secondary position calculated at 0.09. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16592(14) 0.15854(12) 0.31174(9) 0.0586(3) Uani 1 1 d . . . . .
H1 H 0.197343 0.184141 0.391441 0.088 Uiso 1 1 calc R U . . .
O2 O 0.82104(15) 0.22302(14) 0.43379(10) 0.0683(3) Uani 1 1 d . . . . .
H2A H 0.825295 0.260296 0.505162 0.102 Uiso 1 1 calc R U . . .
N1 N 0.26020(17) 0.24881(14) 0.57919(11) 0.0569(3) Uani 1 1 d . . . . .
N2A N 0.2134(19) 0.3778(8) 0.9427(9) 0.0497(9) Uani 0.677(3) 1 d D U P A 1
N3A N 0.2634(10) 0.5148(7) 0.9803(4) 0.0470(8) Uani 0.677(3) 1 d D U P A 1
C17 C 0.215(7) 0.376(3) 0.940(3) 0.051(3) Uani 0.230(3) 1 d D U P A 2
H17 H 0.151413 0.295151 0.97475 0.062 Uiso 0.230(3) 1 calc R U P A 2
C18 C 0.276(4) 0.516(3) 1.0031(14) 0.052(2) Uani 0.230(3) 1 d D U P A 2
H18 H 0.357397 0.595897 0.974693 0.062 Uiso 0.230(3) 1 calc DR U P A 2
N2B N 0.2798(19) 0.4720(18) 0.9289(13) 0.053(2) Uani 0.093(2) 1 d D U P A 3
N3B N 0.1884(18) 0.4020(16) 0.9976(14) 0.053(2) Uani 0.093(2) 1 d D U P A 3
N4 N 0.17673(16) 0.64993(13) 1.32807(10) 0.0547(3) Uani 1 1 d . . . . .
C1 C 0.31740(19) 0.15436(13) 0.28172(12) 0.0475(3) Uani 1 1 d . . . . .
C2 C 0.49272(19) 0.18892(14) 0.37744(12) 0.0483(3) Uani 1 1 d . . . . .
H2 H 0.508427 0.214411 0.465361 0.058 Uiso 1 1 calc R U . . .
C3 C 0.6455(2) 0.18578(14) 0.34306(12) 0.0510(3) Uani 1 1 d . . . . .
C4 C 0.6205(2) 0.14389(16) 0.21174(14) 0.0577(3) Uani 1 1 d . . . . .
H4 H 0.720775 0.139098 0.187756 0.069 Uiso 1 1 calc R U . . .
C5 C 0.4449(2) 0.10963(16) 0.11783(13) 0.0593(4) Uani 1 1 d . . . . .
H5 H 0.428382 0.082487 0.029985 0.071 Uiso 1 1 calc R U . . .
C6 C 0.2925(2) 0.11440(15) 0.15025(13) 0.0559(3) Uani 1 1 d . . . . .
H6 H 0.17532 0.09128 0.085258 0.067 Uiso 1 1 calc R U . . .
C7 C 0.3232(2) 0.39634(17) 0.62868(14) 0.0598(4) Uani 1 1 d . . . . .
H7 H 0.372437 0.467005 0.579901 0.072 Uiso 1 1 calc R U . . .
C8 C 0.3194(2) 0.44958(16) 0.74816(14) 0.0576(3) Uani 1 1 d . . . . .
H8 H 0.366412 0.553449 0.779654 0.069 Uiso 1 1 calc DR U . . .
C9 C 0.24358(19) 0.34421(16) 0.82000(12) 0.0505(3) Uani 1 1 d D . . . .
C10 C 0.1817(2) 0.19196(16) 0.77093(13) 0.0565(3) Uani 1 1 d . . . . .
H10 H 0.132995 0.118851 0.817971 0.068 Uiso 1 1 calc R U . . .
C11 C 0.1930(2) 0.14992(16) 0.65158(14) 0.0577(3) Uani 1 1 d . . . . .
H11 H 0.151498 0.046973 0.619601 0.069 Uiso 1 1 calc R U . . .
C12 C 0.23101(19) 0.55121(16) 1.10348(12) 0.0519(3) Uani 1 1 d D . . . .
C13 C 0.2861(2) 0.70233(17) 1.14691(14) 0.0600(4) Uani 1 1 d . . . . .
H13 H 0.342344 0.774285 1.101292 0.072 Uiso 1 1 calc R U . . .
C14 C 0.2575(2) 0.74625(16) 1.25821(14) 0.0606(4) Uani 1 1 d . . . . .
H14 H 0.296865 0.849565 1.286869 0.073 Uiso 1 1 calc R U . . .
C15 C 0.1213(2) 0.50203(16) 1.28554(13) 0.0551(3) Uani 1 1 d . . . . .
H15 H 0.0639 0.432813 1.332708 0.066 Uiso 1 1 calc R U . . .
C16 C 0.1458(2) 0.44710(16) 1.17407(14) 0.0571(3) Uani 1 1 d . . . . .
H16 H 0.106224 0.343426 1.147192 0.068 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3599(16) . ?
O1 H1 0.82 . ?
O2 C3 1.3569(17) . ?
O2 H2A 0.82 . ?
N1 C11 1.3313(19) . ?
N1 C7 1.3359(18) . ?
N2A N3A 1.236(4) . ?
N2A C9 1.460(6) . ?
N3A C12 1.481(3) . ?
C17 C18 1.318(10) . ?
C17 C9 1.42(2) . ?
C17 H17 0.93 . ?
C18 C12 1.309(12) . ?
C18 H18 0.93 . ?
N2B N3B 1.242(10) . ?
N2B C9 1.536(16) . ?
N3B C12 1.650(16) . ?
N4 C14 1.3311(19) . ?
N4 C15 1.3356(18) . ?
C1 C2 1.3843(18) . ?
C1 C6 1.3904(17) . ?
C2 C3 1.3901(18) . ?
C2 H2 0.93 . ?
C3 C4 1.3918(18) . ?
C4 C5 1.378(2) . ?
C4 H4 0.93 . ?
C5 C6 1.382(2) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.379(2) . ?
C7 H7 0.93 . ?
C8 C9 1.385(2) . ?
C8 H8 0.93 . ?
C9 C10 1.3784(19) . ?
C10 C11 1.3725(19) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 C13 1.367(2) . ?
C12 C16 1.393(2) . ?
C13 C14 1.366(2) . ?
C13 H13 0.93 . ?
C14 H14 0.93 . ?
C15 C16 1.3877(19) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 117.15(12) . . ?
N3A N2A C9 113.2(6) . . ?
N2A N3A C12 114.2(5) . . ?
C18 C17 C9 122.6(19) . . ?
C18 C17 H17 118.7 . . ?
C9 C17 H17 118.7 . . ?
C12 C18 C17 124.6(19) . . ?
C12 C18 H18 117.7 . . ?
C17 C18 H18 117.7 . . ?
N3B N2B C9 103.3(14) . . ?
N2B N3B C12 97.8(13) . . ?
C14 N4 C15 117.24(12) . . ?
O1 C1 C2 122.00(11) . . ?
O1 C1 C6 118.01(12) . . ?
C2 C1 C6 119.98(12) . . ?
C1 C2 C3 120.45(11) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.15(11) . . ?
O2 C3 C4 118.04(12) . . ?
C2 C3 C4 119.80(13) . . ?
C5 C4 C3 118.91(13) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.99(12) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.84(13) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C8 123.59(13) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 118.22(13) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C10 C9 C8 118.59(12) . . ?
C10 C9 C17 115.1(12) . . ?
C8 C9 C17 126.3(12) . . ?
C10 C9 N2A 115.3(3) . . ?
C8 C9 N2A 126.0(3) . . ?
C10 C9 N2B 150.3(5) . . ?
C8 C9 N2B 91.0(5) . . ?
C11 C10 C9 118.97(13) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N1 C11 C10 123.43(13) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C18 C12 C13 116.8(12) . . ?
C18 C12 C16 124.4(12) . . ?
C13 C12 C16 118.57(12) . . ?
C13 C12 N3A 115.0(3) . . ?
C16 C12 N3A 126.4(3) . . ?
C13 C12 N3B 154.8(4) . . ?
C16 C12 N3B 86.3(4) . . ?
C14 C13 C12 119.13(13) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
N4 C14 C13 123.88(13) . . ?
N4 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
N4 C15 C16 122.88(13) . . ?
N4 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C15 C16 C12 118.30(13) . . ?
C15 C16 H16 120.9 . . ?
C12 C16 H16 120.9 . . ?

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
O1 H1 N1 0.82 1.95 2.7688(14) 176.7 . yes
O2 H2A N4 0.82 1.97 2.7861(14) 177.1 2_667 yes

####################################################################### 
# 
# 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_A75_BE25_250
_database_code_depnum_ccdc_archive 'CCDC 1995491'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT077_A75_BE25_250        
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)ethylene molecules within the structure. 
;
_vrf_PLAT230_A75_BE25_250        
;
PROBLEM: Hirshfeld Test Diff for    C12      --C16      .        5.7 s.u.  
RESPONSE: Due to the pedal motion of the 4,4'-azopyridine molecule and not
          modeling the disorder about the pyridine rings.
;
# end Validation Reply Form

_audit_creation_date             2020-03-12T16:25:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C16.45 H14.45 N3.55 O2'
_chemical_formula_weight         293.87

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.00509(19)
_cell_length_b                   9.78356(18)
_cell_length_c                   10.8603(2)
_cell_angle_alpha                93.8151(16)
_cell_angle_beta                 106.4802(19)
_cell_angle_gamma                113.764(2)
_cell_volume                     730.44(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    13463
_cell_measurement_theta_min      4.323
_cell_measurement_theta_max      76.361

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.056
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             308
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 6 -1 0.055
0 4 4 0.0525
0 -6 2 0.0757
3 -6 0 0.0674
5 -1 0 0.0887
5 0 -3 0.0947
0 0 7 0.026
0 0 -7 0.0283
-2 -3 -2 0.0761
-5 0 3 0.0919


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.661
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.854
_shelx_estimated_absorpt_T_max   0.96

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      250(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0285982
_diffrn_orient_matrix_ub_12      -0.165702
_diffrn_orient_matrix_ub_13      -0.0023322
_diffrn_orient_matrix_ub_21      -0.1009774
_diffrn_orient_matrix_ub_22      -0.0394227
_diffrn_orient_matrix_ub_23      -0.1499787
_diffrn_orient_matrix_ub_31      0.1974381
_diffrn_orient_matrix_ub_32      0.043628
_diffrn_orient_matrix_ub_33      -0.0188307
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_number            27550
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.338
_diffrn_reflns_theta_max         77.243
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_reflns_Friedel_coverage         0
_reflns_number_total             3003
_reflns_number_gt                2641
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0664P)²+0.0905P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0049(10)
_refine_ls_number_reflns         3003
_refine_ls_number_parameters     242
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1205
_refine_ls_wR_factor_gt          0.116
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.18
_refine_diff_density_rms         0.036

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)ethylene and the pedal motion about the azo group, the atom 
 sites N2 and N3, were split into parts A and B. These sites were allowed to 
 free refine their site occupancies to a total value of 1. To help maintain 
 reasonable ADP and bond lengths, SIMU, RIGU, and DFIX restraints and 
 constraints were applied. At this temperature the ratio of 4,4'-azopyridine 
 to bis(4-pyridyl)ethylene was 0.78 to 0.22 with the amount of 
 4,4'-azopyridine in the secondary position calculated at 0.07. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16557(13) 0.15964(11) 0.31162(8) 0.0534(3) Uani 1 1 d . . . . .
H1 H 0.197807 0.186395 0.392255 0.08 Uiso 1 1 calc R U . . .
O2 O 0.82228(14) 0.22356(12) 0.43391(9) 0.0624(3) Uani 1 1 d . . . . .
H2A H 0.826747 0.261792 0.506027 0.094 Uiso 1 1 calc R U . . .
N1 N 0.26025(16) 0.24892(13) 0.57924(10) 0.0526(3) Uani 1 1 d . . . . .
N2A N 0.2136(19) 0.3763(7) 0.9430(8) 0.0458(9) Uani 0.707(3) 1 d D U P A 1
N3A N 0.2685(11) 0.5145(7) 0.9820(5) 0.0445(6) Uani 0.707(3) 1 d D U P A 1
C17 C 0.213(7) 0.381(3) 0.938(3) 0.047(3) Uani 0.225(3) 1 d D U P A 2
H17 H 0.155989 0.299639 0.976944 0.057 Uiso 0.225(3) 1 calc R U P A 2
C18 C 0.258(4) 0.519(3) 0.9978(17) 0.045(2) Uani 0.225(3) 1 d D U P A 2
H18 H 0.314616 0.600753 0.958757 0.054 Uiso 0.225(3) 1 calc DR U P A 2
N2B N 0.281(3) 0.475(2) 0.9293(17) 0.049(3) Uani 0.068(2) 1 d D U P A 3
N3B N 0.188(2) 0.403(2) 0.9964(17) 0.050(2) Uani 0.068(2) 1 d D U P A 3
N4 N 0.17640(15) 0.65015(12) 1.32797(10) 0.0504(3) Uani 1 1 d . . . . .
C1 C 0.31736(18) 0.15526(12) 0.28167(11) 0.0436(3) Uani 1 1 d . . . . .
C2 C 0.49305(18) 0.18963(13) 0.37755(11) 0.0448(3) Uani 1 1 d . . . . .
H2 H 0.508949 0.215435 0.466428 0.054 Uiso 1 1 calc R U . . .
C3 C 0.64631(19) 0.18621(13) 0.34311(12) 0.0473(3) Uani 1 1 d . . . . .
C4 C 0.6211(2) 0.14410(14) 0.21168(13) 0.0530(3) Uani 1 1 d . . . . .
H4 H 0.722579 0.138936 0.187475 0.064 Uiso 1 1 calc R U . . .
C5 C 0.4452(2) 0.11014(15) 0.11768(12) 0.0549(3) Uani 1 1 d . . . . .
H5 H 0.428557 0.082902 0.028861 0.066 Uiso 1 1 calc R U . . .
C6 C 0.2922(2) 0.11493(14) 0.15008(12) 0.0517(3) Uani 1 1 d . . . . .
H6 H 0.173394 0.091336 0.084361 0.062 Uiso 1 1 calc R U . . .
C7 C 0.3233(2) 0.39660(15) 0.62908(13) 0.0549(3) Uani 1 1 d . . . . .
H7 H 0.373026 0.46841 0.579833 0.066 Uiso 1 1 calc R U . . .
C8 C 0.3194(2) 0.44948(15) 0.74871(13) 0.0525(3) Uani 1 1 d . . . . .
H8 H 0.367145 0.554513 0.780784 0.063 Uiso 1 1 calc DR U . . .
C9 C 0.24290(17) 0.34322(14) 0.82035(11) 0.0458(3) Uani 1 1 d D . . . .
C10 C 0.18111(19) 0.19064(15) 0.77114(13) 0.0517(3) Uani 1 1 d . . . . .
H10 H 0.131886 0.116364 0.818623 0.062 Uiso 1 1 calc R U . . .
C11 C 0.1928(2) 0.14918(15) 0.65140(13) 0.0533(3) Uani 1 1 d . . . . .
H11 H 0.151117 0.045149 0.618863 0.064 Uiso 1 1 calc R U . . .
C12 C 0.23152(18) 0.55207(15) 1.10325(11) 0.0467(3) Uani 1 1 d D . . . .
C13 C 0.2867(2) 0.70374(15) 1.14685(13) 0.0544(3) Uani 1 1 d . . . . .
H13 H 0.343717 0.776734 1.100738 0.065 Uiso 1 1 calc R U . . .
C14 C 0.2578(2) 0.74759(15) 1.25864(13) 0.0555(3) Uani 1 1 d . . . . .
H14 H 0.29746 0.852027 1.287852 0.067 Uiso 1 1 calc R U . . .
C15 C 0.12132(19) 0.50218(15) 1.28518(12) 0.0511(3) Uani 1 1 d . . . . .
H15 H 0.063113 0.431858 1.332797 0.061 Uiso 1 1 calc R U . . .
C16 C 0.1460(2) 0.44758(15) 1.17389(13) 0.0516(3) Uani 1 1 d . . . . .
H16 H 0.106101 0.342717 1.146758 0.062 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3595(15) . ?
O1 H1 0.83 . ?
O2 C3 1.3562(16) . ?
O2 H2A 0.83 . ?
N1 C11 1.3323(18) . ?
N1 C7 1.3374(17) . ?
N2A N3A 1.240(4) . ?
N2A C9 1.455(5) . ?
N3A C12 1.483(3) . ?
C17 C18 1.321(10) . ?
C17 C9 1.414(19) . ?
C17 H17 0.94 . ?
C18 C12 1.265(9) . ?
C18 H18 0.94 . ?
N2B N3B 1.242(10) . ?
N2B C9 1.56(2) . ?
N3B C12 1.65(2) . ?
N4 C14 1.3317(18) . ?
N4 C15 1.3364(17) . ?
C1 C2 1.3845(17) . ?
C1 C6 1.3915(16) . ?
C2 C3 1.3921(17) . ?
C2 H2 0.94 . ?
C3 C4 1.3926(17) . ?
C4 C5 1.378(2) . ?
C4 H4 0.94 . ?
C5 C6 1.383(2) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3795(18) . ?
C7 H7 0.94 . ?
C8 C9 1.3878(19) . ?
C8 H8 0.94 . ?
C9 C10 1.3811(17) . ?
C10 C11 1.3762(18) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.3714(19) . ?
C12 C16 1.3930(19) . ?
C13 C14 1.3720(19) . ?
C13 H13 0.94 . ?
C14 H14 0.94 . ?
C15 C16 1.3856(18) . ?
C15 H15 0.94 . ?
C16 H16 0.94 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 117.21(11) . . ?
N3A N2A C9 112.9(5) . . ?
N2A N3A C12 114.5(4) . . ?
C18 C17 C9 126.2(19) . . ?
C18 C17 H17 116.9 . . ?
C9 C17 H17 116.9 . . ?
C12 C18 C17 125.8(17) . . ?
C12 C18 H18 117.1 . . ?
C17 C18 H18 117.1 . . ?
N3B N2B C9 101.3(18) . . ?
N2B N3B C12 97.0(16) . . ?
C14 N4 C15 117.41(11) . . ?
O1 C1 C2 121.97(10) . . ?
O1 C1 C6 118.01(11) . . ?
C2 C1 C6 120.02(11) . . ?
C1 C2 C3 120.39(10) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.09(10) . . ?
O2 C3 C4 118.11(11) . . ?
C2 C3 C4 119.79(12) . . ?
C5 C4 C3 118.95(12) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.98(11) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.84(12) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C8 123.69(12) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 118.12(12) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C10 C9 C8 118.69(11) . . ?
C10 C9 C17 117.5(11) . . ?
C8 C9 C17 123.7(11) . . ?
C10 C9 N2A 115.4(3) . . ?
C8 C9 N2A 125.9(3) . . ?
C10 C9 N2B 151.5(6) . . ?
C8 C9 N2B 89.8(6) . . ?
C11 C10 C9 118.87(12) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.37(12) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C18 C12 C13 115.8(11) . . ?
C18 C12 C16 125.6(11) . . ?
C13 C12 C16 118.54(12) . . ?
C13 C12 N3A 115.7(3) . . ?
C16 C12 N3A 125.7(3) . . ?
C13 C12 N3B 154.7(5) . . ?
C16 C12 N3B 86.4(5) . . ?
C12 C13 C14 119.16(12) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
N4 C14 C13 123.52(12) . . ?
N4 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
N4 C15 C16 123.06(12) . . ?
N4 C15 H15 118.5 . . ?
C16 C15 H15 118.5 . . ?
C15 C16 C12 118.30(12) . . ?
C15 C16 H16 120.9 . . ?
C12 C16 H16 120.9 . . ?

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
O1 H1 N1 0.83 1.94 2.7684(14) 177.1 . yes
O2 H2A N4 0.83 1.96 2.7862(14) 177.1 2_667 yes

####################################################################### 
# 
# 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_A75_BE25_290
_database_code_depnum_ccdc_archive 'CCDC 1995493'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT230_A75_BE25_290        
;
PROBLEM: Hirshfeld Test Diff for    C12      --C16      .        7.5 s.u.  
RESPONSE: Due to the pedal motion of the 4,4'-azopyridine molecule and not
          modeling the disorder about the pyridine rings.
;
_vrf_PLAT077_A75_BE25_290        
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)ethylene molecules within the structure. 
;
# end Validation Reply Form

_audit_creation_date             2020-03-12T16:26:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C16.46 H14.46 N3.54 O2'
_chemical_formula_weight         293.86

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.04776(11)
_cell_length_b                   9.80445(15)
_cell_length_c                   10.87711(16)
_cell_angle_alpha                94.0306(12)
_cell_angle_beta                 106.4496(13)
_cell_angle_gamma                113.6558(14)
_cell_volume                     737.25(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    11987
_cell_measurement_theta_min      4.305
_cell_measurement_theta_max      75.381

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.056
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             308
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 6 -1 0.055
0 4 4 0.0525
0 -6 2 0.0757
3 -6 0 0.0674
5 -1 0 0.0887
5 0 -3 0.0947
0 0 7 0.026
0 0 -7 0.0283
-2 -3 -2 0.0761
-5 0 3 0.0919


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.659
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.856
_shelx_estimated_absorpt_T_max   0.96

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      290(2)
_diffrn_ambient_environment      air
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0289254
_diffrn_orient_matrix_ub_12      -0.1655213
_diffrn_orient_matrix_ub_13      -0.0032032
_diffrn_orient_matrix_ub_21      -0.0990228
_diffrn_orient_matrix_ub_22      -0.0386061
_diffrn_orient_matrix_ub_23      -0.1499409
_diffrn_orient_matrix_ub_31      0.1969073
_diffrn_orient_matrix_ub_32      0.0434529
_diffrn_orient_matrix_ub_33      -0.0177724
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_number            27841
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.334
_diffrn_reflns_theta_max         77.209
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.969
_reflns_Friedel_coverage         0
_reflns_number_total             3036
_reflns_number_gt                2556
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0693P)²+0.0779P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0051(11)
_refine_ls_number_reflns         3036
_refine_ls_number_parameters     242
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1308
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)ethylene and the pedal motion about the azo group, the atom 
 sites N2 and N3, were split into parts A and B. These sites were allowed to 
 free refine their site occupancies to a total value of 1. To help maintain 
 reasonable ADP and bond lengths, SIMU, RIGU, and DFIX restraints and 
 constraints were applied. At this temperature the ratio of 4,4'-azopyridine 
 to bis(4-pyridyl)ethylene was 0.77 to 0.23 with the amount of 
 4,4'-azopyridine in the secondary position calculated at 0.13. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16621(14) 0.15727(12) 0.31178(9) 0.0642(3) Uani 1 1 d . . . . .
H1 H 0.197149 0.182119 0.391486 0.096 Uiso 1 1 calc R U . . .
O2 O 0.81971(15) 0.22252(14) 0.43349(10) 0.0751(3) Uani 1 1 d . . . . .
H2A H 0.823381 0.258646 0.505071 0.113 Uiso 1 1 calc R U . . .
N1 N 0.25980(17) 0.24845(14) 0.57913(11) 0.0617(3) Uani 1 1 d . . . . .
N2A N 0.213(2) 0.3765(9) 0.9425(9) 0.0543(10) Uani 0.645(3) 1 d D U P A 1
N3A N 0.2687(13) 0.5136(8) 0.9823(6) 0.0529(8) Uani 0.645(3) 1 d D U P A 1
C17 C 0.219(7) 0.381(3) 0.940(3) 0.054(3) Uani 0.229(3) 1 d D U P A 2
H17 H 0.17316 0.30262 0.982603 0.065 Uiso 0.229(3) 1 calc R U P A 2
C18 C 0.255(4) 0.519(3) 0.9943(19) 0.054(2) Uani 0.229(3) 1 d D U P A 2
H18 H 0.300343 0.598283 0.952089 0.064 Uiso 0.229(3) 1 calc DR U P A 2
N2B N 0.2791(15) 0.4714(15) 0.9278(11) 0.058(2) Uani 0.126(2) 1 d D U P A 3
N3B N 0.1906(15) 0.4029(13) 0.9977(11) 0.0579(19) Uani 0.126(2) 1 d D U P A 3
N4 N 0.17741(17) 0.64978(14) 1.32806(11) 0.0594(3) Uani 1 1 d . . . . .
C1 C 0.3174(2) 0.15329(13) 0.28186(12) 0.0518(3) Uani 1 1 d . . . . .
C2 C 0.49240(19) 0.18806(14) 0.37742(12) 0.0528(3) Uani 1 1 d . . . . .
H2 H 0.508174 0.21352 0.465325 0.063 Uiso 1 1 calc R U . . .
C3 C 0.6447(2) 0.18519(15) 0.34289(13) 0.0559(3) Uani 1 1 d . . . . .
C4 C 0.6200(2) 0.14350(16) 0.21188(14) 0.0631(4) Uani 1 1 d . . . . .
H4 H 0.719912 0.138682 0.187901 0.076 Uiso 1 1 calc R U . . .
C5 C 0.4450(2) 0.10943(16) 0.11812(13) 0.0651(4) Uani 1 1 d . . . . .
H5 H 0.428782 0.08288 0.030278 0.078 Uiso 1 1 calc R U . . .
C6 C 0.2930(2) 0.11350(16) 0.15054(13) 0.0614(4) Uani 1 1 d . . . . .
H6 H 0.17608 0.089981 0.085535 0.074 Uiso 1 1 calc R U . . .
C7 C 0.3234(2) 0.39613(17) 0.62838(15) 0.0656(4) Uani 1 1 d . . . . .
H7 H 0.372706 0.466369 0.579587 0.079 Uiso 1 1 calc R U . . .
C8 C 0.3197(2) 0.44981(17) 0.74759(15) 0.0636(4) Uani 1 1 d . . . . .
H8 H 0.366596 0.553646 0.778884 0.076 Uiso 1 1 calc DR U . . .
C9 C 0.2443(2) 0.34518(16) 0.81963(13) 0.0557(3) Uani 1 1 d D . . . .
C10 C 0.1823(2) 0.19334(17) 0.77106(14) 0.0622(4) Uani 1 1 d . . . . .
H10 H 0.134056 0.120734 0.818339 0.075 Uiso 1 1 calc R U . . .
C11 C 0.1929(2) 0.15063(17) 0.65186(14) 0.0631(4) Uani 1 1 d . . . . .
H11 H 0.150887 0.047605 0.620067 0.076 Uiso 1 1 calc R U . . .
C12 C 0.2305(2) 0.54994(18) 1.10374(13) 0.0583(3) Uani 1 1 d D . . . .
C13 C 0.2854(2) 0.70048(18) 1.14679(15) 0.0663(4) Uani 1 1 d . . . . .
H13 H 0.341213 0.771941 1.100924 0.08 Uiso 1 1 calc R U . . .
C14 C 0.2577(2) 0.74522(17) 1.25790(15) 0.0660(4) Uani 1 1 d . . . . .
H14 H 0.29724 0.848566 1.286315 0.079 Uiso 1 1 calc R U . . .
C15 C 0.1217(2) 0.50210(17) 1.28585(14) 0.0606(3) Uani 1 1 d . . . . .
H15 H 0.064322 0.43335 1.333108 0.073 Uiso 1 1 calc R U . . .
C16 C 0.1455(2) 0.44659(17) 1.17437(14) 0.0631(4) Uani 1 1 d . . . . .
H16 H 0.105777 0.342925 1.14757 0.076 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3593(16) . ?
O1 H1 0.82 . ?
O2 C3 1.3560(17) . ?
O2 H2A 0.82 . ?
N1 C11 1.3301(19) . ?
N1 C7 1.3366(19) . ?
N2A N3A 1.232(4) . ?
N2A C9 1.464(6) . ?
N3A C12 1.490(4) . ?
C17 C18 1.317(10) . ?
C17 C9 1.42(2) . ?
C17 H17 0.93 . ?
C18 C12 1.294(9) . ?
C18 H18 0.93 . ?
N2B N3B 1.237(9) . ?
N2B C9 1.525(13) . ?
N3B C12 1.643(13) . ?
N4 C14 1.330(2) . ?
N4 C15 1.3331(18) . ?
C1 C2 1.3844(19) . ?
C1 C6 1.3902(18) . ?
C2 C3 1.3894(19) . ?
C2 H2 0.93 . ?
C3 C4 1.3891(18) . ?
C4 C5 1.377(2) . ?
C4 H4 0.93 . ?
C5 C6 1.380(2) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.378(2) . ?
C7 H7 0.93 . ?
C8 C9 1.385(2) . ?
C8 H8 0.93 . ?
C9 C10 1.374(2) . ?
C10 C11 1.3704(19) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 C13 1.362(2) . ?
C12 C16 1.391(2) . ?
C13 C14 1.364(2) . ?
C13 H13 0.93 . ?
C14 H14 0.93 . ?
C15 C16 1.388(2) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 117.03(12) . . ?
N3A N2A C9 112.3(6) . . ?
N2A N3A C12 114.0(5) . . ?
C18 C17 C9 124.1(19) . . ?
C18 C17 H17 117.9 . . ?
C9 C17 H17 117.9 . . ?
C12 C18 C17 123.3(18) . . ?
C12 C18 H18 118.4 . . ?
C17 C18 H18 118.4 . . ?
N3B N2B C9 104.1(12) . . ?
N2B N3B C12 99.0(10) . . ?
C14 N4 C15 117.22(12) . . ?
O1 C1 C2 122.10(11) . . ?
O1 C1 C6 118.11(12) . . ?
C2 C1 C6 119.79(13) . . ?
C1 C2 C3 120.44(11) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C4 118.02(13) . . ?
O2 C3 C2 122.10(11) . . ?
C4 C3 C2 119.88(13) . . ?
C5 C4 C3 118.88(13) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.99(12) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.98(14) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.47(14) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 118.29(14) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C10 C9 C8 118.64(13) . . ?
C10 C9 C17 116.2(12) . . ?
C8 C9 C17 125.1(12) . . ?
C10 C9 N2A 114.2(4) . . ?
C8 C9 N2A 127.1(3) . . ?
C10 C9 N2B 149.8(4) . . ?
C8 C9 N2B 91.5(4) . . ?
C11 C10 C9 118.94(14) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N1 C11 C10 123.59(13) . . ?
N1 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
C18 C12 C13 114.2(12) . . ?
C18 C12 C16 127.1(12) . . ?
C13 C12 C16 118.56(13) . . ?
C13 C12 N3A 114.9(3) . . ?
C16 C12 N3A 126.5(3) . . ?
C13 C12 N3B 154.0(3) . . ?
C16 C12 N3B 87.2(3) . . ?
C12 C13 C14 119.24(14) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
N4 C14 C13 123.88(14) . . ?
N4 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
N4 C15 C16 122.79(14) . . ?
N4 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C15 C16 C12 118.32(14) . . ?
C15 C16 H16 120.8 . . ?
C12 C16 H16 120.8 . . ?

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
O1 H1 N1 0.82 1.95 2.7707(15) 176.1 . yes
O2 H2A N4 0.82 1.97 2.7895(15) 176.8 2_667 yes

####################################################################### 
# 
# 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_A75_BE25_190
_database_code_depnum_ccdc_archive 'CCDC 1995488'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT077_A75_BE25_190        
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)ethylene molecules within the structure. 
;
# end Validation Reply Form

_audit_creation_date             2020-04-02T13:30:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C16.50 H14.50 N3.50 O2'
_chemical_formula_weight         293.82

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9561(2)
_cell_length_b                   9.75452(15)
_cell_length_c                   10.8395(2)
_cell_angle_alpha                93.5338(16)
_cell_angle_beta                 106.566(2)
_cell_angle_gamma                113.8855(19)
_cell_volume                     722.05(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    15572
_cell_measurement_theta_min      4.321
_cell_measurement_theta_max      76.874

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.056
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             308
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 6 -1 0.055
5 0 -3 0.0947
3 -6 0 0.0674
0 -6 2 0.0757
-5 0 3 0.0919
0 0 -7 0.0283
5 -1 0 0.0887
0 0 7 0.026
0 4 4 0.0525
-2 -3 -2 0.0761


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.75
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.656
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.853
_shelx_estimated_absorpt_T_max   0.959

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      190(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0288333
_diffrn_orient_matrix_ub_12      -0.1662221
_diffrn_orient_matrix_ub_13      -0.0021205
_diffrn_orient_matrix_ub_21      -0.1070004
_diffrn_orient_matrix_ub_22      -0.0402865
_diffrn_orient_matrix_ub_23      -0.1496447
_diffrn_orient_matrix_ub_31      0.1960084
_diffrn_orient_matrix_ub_32      0.0430281
_diffrn_orient_matrix_ub_33      -0.0229078
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_number            27314
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.345
_diffrn_reflns_theta_max         77.258
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_reflns_Friedel_coverage         0
_reflns_number_total             2987
_reflns_number_gt                2731
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0612P)²+0.1131P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0047(9)
_refine_ls_number_reflns         2987
_refine_ls_number_parameters     242
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1083
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.036

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 To help model the substitution of the 4,4'-azopyridine with 
 bis(4-pyridyl)ethylene and the pedal motion about the azo group, the atom 
 sites N2 and N3, were split into parts A and B. These sites were allowed to 
 free refine their site occupancies to a total value of 1. To help maintain 
 reasonable ADP and bond lengths, SIMU, RIGU, and DFIX restraints and 
 constraints were applied. At this temperature the ratio of 4,4'-azopyridine 
 to bis(4-pyridyl)ethylene was 0.75 to 0.25 with the amount of 
 4,4'-azopyridine in the secondary position calculated at 0.02. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1 O 0.16434(11) 0.16192(9) 0.31149(7) 0.0400(2) Uani 1 1 d . . . . .
H1 H 0.197071 0.188106 0.393281 0.06 Uiso 1 1 calc R U . . .
O2 O 0.82507(12) 0.22415(10) 0.43470(8) 0.0462(2) Uani 1 1 d . . . . .
H2A H 0.829878 0.263654 0.507474 0.069 Uiso 1 1 calc R U . . .
N1 N 0.26106(14) 0.24942(11) 0.57918(9) 0.0404(2) Uani 1 1 d . . . . .
N2A N 0.2137(15) 0.3755(6) 0.9440(7) 0.0349(9) Uani 0.732(3) 1 d D U P A 1
N3A N 0.2687(10) 0.5148(6) 0.9813(4) 0.0330(6) Uani 0.732(3) 1 d D U P A 1
C17 C 0.211(5) 0.382(2) 0.936(3) 0.035(2) Uani 0.248(3) 1 d D U P A 2
H17 H 0.144827 0.299039 0.97292 0.042 Uiso 0.248(3) 1 calc R U P A 2
C18 C 0.262(4) 0.520(2) 0.9998(14) 0.0327(18) Uani 0.248(3) 1 d D U P A 2
H18 H 0.327476 0.60375 0.963494 0.039 Uiso 0.248(3) 1 calc DR U P A 2
N2B N 0.284(7) 0.478(6) 0.927(5) 0.037(3) Uani 0.020(2) 1 d D U P A 3
N3B N 0.181(7) 0.400(6) 0.987(5) 0.037(3) Uani 0.020(2) 1 d D U P A 3
N4 N 0.17507(14) 0.65036(11) 1.32810(9) 0.0387(2) Uani 1 1 d . . . . .
C1 C 0.31665(16) 0.15686(11) 0.28138(10) 0.0336(2) Uani 1 1 d . . . . .
C2 C 0.49397(16) 0.19134(11) 0.37781(10) 0.0342(2) Uani 1 1 d . . . . .
H2 H 0.510438 0.217976 0.467696 0.041 Uiso 1 1 calc R U . . .
C3 C 0.64797(16) 0.18706(12) 0.34333(11) 0.0359(2) Uani 1 1 d . . . . .
C4 C 0.62261(18) 0.14455(13) 0.21168(11) 0.0401(3) Uani 1 1 d . . . . .
H4 H 0.725726 0.139078 0.187358 0.048 Uiso 1 1 calc R U . . .
C5 C 0.44480(19) 0.11050(13) 0.11710(11) 0.0415(3) Uani 1 1 d . . . . .
H5 H 0.427617 0.08244 0.027274 0.05 Uiso 1 1 calc R U . . .
C6 C 0.29098(18) 0.11608(12) 0.14945(11) 0.0394(3) Uani 1 1 d . . . . .
H6 H 0.170165 0.09254 0.082894 0.047 Uiso 1 1 calc R U . . .
C7 C 0.32402(17) 0.39756(13) 0.62955(12) 0.0414(3) Uani 1 1 d . . . . .
H7 H 0.374717 0.470987 0.579914 0.05 Uiso 1 1 calc R U . . .
C8 C 0.31946(17) 0.44956(13) 0.74926(11) 0.0391(3) Uani 1 1 d . . . . .
H8 H 0.367653 0.555858 0.781819 0.047 Uiso 1 1 calc DR U . . .
C9 C 0.24222(15) 0.34176(12) 0.82096(10) 0.0338(2) Uani 1 1 d D . . . .
C10 C 0.17979(17) 0.18812(13) 0.77119(11) 0.0386(3) Uani 1 1 d . . . . .
H10 H 0.129065 0.112161 0.818841 0.046 Uiso 1 1 calc R U . . .
C11 C 0.19288(17) 0.14789(13) 0.65108(11) 0.0402(3) Uani 1 1 d . . . . .
H11 H 0.151313 0.042746 0.617954 0.048 Uiso 1 1 calc R U . . .
C12 C 0.23227(15) 0.55346(13) 1.10289(10) 0.0344(2) Uani 1 1 d D . . . .
C13 C 0.28810(17) 0.70660(13) 1.14674(11) 0.0403(3) Uani 1 1 d . . . . .
H13 H 0.346752 0.781089 1.100376 0.048 Uiso 1 1 calc R U . . .
C14 C 0.25738(17) 0.74970(13) 1.25890(12) 0.0416(3) Uani 1 1 d . . . . .
H14 H 0.296726 0.855301 1.288418 0.05 Uiso 1 1 calc R U . . .
C15 C 0.12005(17) 0.50162(13) 1.28458(11) 0.0383(3) Uani 1 1 d . . . . .
H15 H 0.060448 0.429598 1.332409 0.046 Uiso 1 1 calc R U . . .
C16 C 0.14585(17) 0.44808(13) 1.17359(11) 0.0379(3) Uani 1 1 d . . . . .
H16 H 0.105593 0.341916 1.146183 0.046 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C1 1.3599(13) . ?
O1 H1 0.84 . ?
O2 C3 1.3581(14) . ?
O2 H2A 0.84 . ?
N1 C11 1.3356(15) . ?
N1 C7 1.3408(15) . ?
N2A N3A 1.246(4) . ?
N2A C9 1.455(5) . ?
N3A C12 1.486(3) . ?
C17 C18 1.323(10) . ?
C17 C9 1.403(18) . ?
C17 H17 0.95 . ?
C18 C12 1.255(9) . ?
C18 H18 0.95 . ?
N2B N3B 1.241(10) . ?
N2B C9 1.56(6) . ?
N3B C12 1.72(6) . ?
N4 C14 1.3365(15) . ?
N4 C15 1.3426(15) . ?
C1 C2 1.3883(15) . ?
C1 C6 1.3937(15) . ?
C2 C3 1.3940(16) . ?
C2 H2 0.95 . ?
C3 C4 1.3943(15) . ?
C4 C5 1.3832(17) . ?
C4 H4 0.95 . ?
C5 C6 1.3857(17) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.3795(16) . ?
C7 H7 0.95 . ?
C8 C9 1.3918(16) . ?
C8 H8 0.95 . ?
C9 C10 1.3888(15) . ?
C10 C11 1.3810(16) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
C12 C13 1.3818(16) . ?
C12 C16 1.3936(16) . ?
C13 C14 1.3799(17) . ?
C13 H13 0.95 . ?
C14 H14 0.95 . ?
C15 C16 1.3829(16) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?

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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 117.32(10) . . ?
N3A N2A C9 112.4(5) . . ?
N2A N3A C12 114.2(4) . . ?
C18 C17 C9 128.1(17) . . ?
C18 C17 H17 116 . . ?
C9 C17 H17 116 . . ?
C12 C18 C17 127.0(16) . . ?
C12 C18 H18 116.5 . . ?
C17 C18 H18 116.5 . . ?
N3B N2B C9 96(5) . . ?
N2B N3B C12 95(5) . . ?
C14 N4 C15 117.43(10) . . ?
O1 C1 C2 121.81(9) . . ?
O1 C1 C6 118.10(10) . . ?
C2 C1 C6 120.09(10) . . ?
C1 C2 C3 120.30(9) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 121.90(9) . . ?
O2 C3 C4 118.17(10) . . ?
C2 C3 C4 119.92(10) . . ?
C5 C4 C3 118.88(11) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.96(10) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.82(11) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C8 123.82(11) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.07(10) . . ?
C7 C8 H8 121 . . ?
C9 C8 H8 121 . . ?
C10 C9 C8 118.75(10) . . ?
C10 C9 C17 118.9(9) . . ?
C8 C9 C17 122.2(9) . . ?
C10 C9 N2A 115.9(3) . . ?
C8 C9 N2A 125.3(3) . . ?
C10 C9 N2B 153.9(15) . . ?
C8 C9 N2B 87.3(15) . . ?
C11 C10 C9 118.71(10) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.28(10) . . ?
N1 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
C18 C12 C13 116.4(9) . . ?
C18 C12 C16 125.0(9) . . ?
C13 C12 C16 118.55(10) . . ?
C13 C12 N3A 116.3(2) . . ?
C16 C12 N3A 125.2(2) . . ?
C13 C12 N3B 153.3(14) . . ?
C16 C12 N3B 87.5(14) . . ?
C14 C13 C12 119.00(10) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
N4 C14 C13 123.30(11) . . ?
N4 C14 H14 118.4 . . ?
C13 C14 H14 118.4 . . ?
N4 C15 C16 123.25(10) . . ?
N4 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C15 C16 C12 118.46(10) . . ?
C15 C16 H16 120.8 . . ?
C12 C16 H16 120.8 . . ?

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
O1 H1 N1 0.84 1.92 2.7621(12) 177.3 . yes
O2 H2A N4 0.84 1.94 2.7792(12) 176.8 2_667 yes

