# 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_BE25_BA75_190
_database_code_depnum_ccdc_archive 'CCDC 1995687'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT155_BE25_BA75_190       
;
PROBLEM: The Triclinic Unitcell is NOT Reduced ..........     Please Do !  
RESPONSE: The unit cell was not reduced to keep the values consistent throughout
          various temperature measurements.
;
# end Validation Reply Form

_audit_creation_date             2020-04-02T10:30:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C18 H14.61 N2 O2'
_chemical_formula_weight         290.92

#----------------------------------------------------------------------------#
#                   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                   8.1603(2)
_cell_length_b                   9.8060(3)
_cell_length_c                   10.9374(2)
_cell_angle_alpha                92.130(3)
_cell_angle_beta                 108.187(2)
_cell_angle_gamma                114.618(2)
_cell_volume                     741.61(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    10959
_cell_measurement_theta_min      4.319
_cell_measurement_theta_max      77.022

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

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.082
_exptl_crystal_density_diffrn    1.303
_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
2 -4 -1 0.0431
-5 -1 -4 0.0754
-5 -4 0 0.0393
-1 4 5 0.0478
0 3 -5 0.0753
0 -3 -6 0.0824
5 5 0 0.0431
-2 4 2 0.0449
-2 -6 -1 0.0344
3 6 5 0.0681
-5 -1 1 0.0424
-3 1 4 0.0384
-3 -3 4 0.0674
3 3 -4 0.0729
1 0 7 0.0918
1 3 7 0.0812
-3 2 -5 0.0856
0 -6 -4 0.0552

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

_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.94947
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.945

#----------------------------------------------------------------------------#
#                   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      0.1332736
_diffrn_orient_matrix_ub_12      0.0490232
_diffrn_orient_matrix_ub_13      0.0354945
_diffrn_orient_matrix_ub_21      -0.0519622
_diffrn_orient_matrix_ub_22      -0.0757116
_diffrn_orient_matrix_ub_23      0.1444376
_diffrn_orient_matrix_ub_31      0.1573572
_diffrn_orient_matrix_ub_32      -0.1512967
_diffrn_orient_matrix_ub_33      -0.0267242
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_number            14653
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_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         77.439
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.973
_reflns_Friedel_coverage         0
_reflns_number_total             3073
_reflns_number_gt                2817
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_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)+(0.0469P)²+0.0813P] 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       0.0035(7)
_refine_ls_number_reflns         3073
_refine_ls_number_parameters     265
_refine_ls_number_restraints     438
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.03

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

_refine_special_details          
;
 To help model the substitution of the bis(4-pyridyl)acetylene with 
 1,2-bis(4-pyridyl)ethylene, the atom sites N2 and  C14 < C18, were split into
 parts A and B. These sites along with C12, C13 (BPE), C19 and C20 (BPA) 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 BPA to BPE was 0.31
 to 0.69.
;

#----------------------------------------------------------------------------#
#                   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 0.16673(10) 0.14786(8) 0.30455(7) 0.04067(18) Uani 1 1 d . . . . .
H1 H 0.200554 0.173878 0.385988 0.061 Uiso 1 1 calc R U . . .
O2 O 0.81959(10) 0.21562(9) 0.43371(7) 0.0469(2) Uani 1 1 d . . . . .
H2A H 0.825512 0.253007 0.506229 0.07 Uiso 1 1 calc R U . . .
N1 N 0.26298(12) 0.24298(10) -0.43254(8) 0.0421(2) Uani 1 1 d . . . . .
C1 C 0.31724(13) 0.14750(9) 0.27613(9) 0.0340(2) Uani 1 1 d . . . . .
C2 C 0.49284(13) 0.18068(10) 0.37405(8) 0.0340(2) Uani 1 1 d . . . . .
H2 H 0.509381 0.203722 0.46352 0.041 Uiso 1 1 calc R U . . .
C3 C 0.64473(14) 0.18026(10) 0.34139(9) 0.0365(2) Uani 1 1 d . . . . .
C4 C 0.61958(16) 0.14323(11) 0.21045(10) 0.0431(2) Uani 1 1 d . . . . .
H4 H 0.721459 0.14066 0.187453 0.052 Uiso 1 1 calc R U . . .
C5 C 0.44376(17) 0.11028(12) 0.11450(10) 0.0463(3) Uani 1 1 d . . . . .
H5 H 0.426406 0.085572 0.025084 0.056 Uiso 1 1 calc R U . . .
C6 C 0.29209(15) 0.11229(11) 0.14510(9) 0.0417(2) Uani 1 1 d . . . . .
H6 H 0.172776 0.089945 0.07761 0.05 Uiso 1 1 calc R U . . .
C7 C 0.19766(14) 0.14688(11) -0.35647(10) 0.0406(2) Uani 1 1 d . . . . .
H7 H 0.153691 0.040852 -0.385071 0.049 Uiso 1 1 calc R U . . .
C8 C 0.19070(14) 0.19362(11) -0.23835(9) 0.0387(2) Uani 1 1 d . . . . .
H8 H 0.141652 0.120908 -0.187895 0.046 Uiso 1 1 calc R U . . .
C9 C 0.25652(13) 0.34873(11) -0.19417(9) 0.0356(2) Uani 1 1 d D . . . .
C10 C 0.32989(15) 0.44984(11) -0.27135(10) 0.0413(2) Uani 1 1 d . . . . .
H10 H 0.379981 0.556908 -0.243716 0.05 Uiso 1 1 calc R U . . .
C11 C 0.32855(15) 0.39191(12) -0.38844(10) 0.0439(2) Uani 1 1 d . . . . .
H11 H 0.37707 0.46186 -0.440978 0.053 Uiso 1 1 calc R U . . .
C12 C 0.2193(17) 0.3803(10) -0.0671(11) 0.0287(13) Uani 0.303(10) 1 d D U P A 1
H12 H 0.160509 0.296269 -0.029079 0.034 Uiso 0.303(10) 1 calc R U P A 1
C13 C 0.2655(7) 0.5177(8) -0.0107(5) 0.0300(11) Uani 0.303(10) 1 d D U P A 1
H13 H 0.329462 0.599223 -0.049097 0.036 Uiso 0.303(10) 1 calc R U P A 1
C14A C 0.2287(18) 0.5624(12) 0.1099(9) 0.0307(17) Uani 0.303(10) 1 d DG U P A 1
C15A C 0.1474(18) 0.4509(9) 0.1770(10) 0.0352(18) Uani 0.303(10) 1 d G U P A 1
H15A H 0.11466 0.34725 0.14768 0.042 Uiso 0.303(10) 1 calc R U P A 1
C16A C 0.1141(18) 0.4910(12) 0.2869(10) 0.0344(19) Uani 0.303(10) 1 d G U P A 1
H16A H 0.058622 0.414754 0.33276 0.041 Uiso 0.303(10) 1 calc R U P A 1
N2A N 0.162(2) 0.6426(13) 0.3298(10) 0.0308(17) Uani 0.303(10) 1 d G U P A 1
C17A C 0.243(2) 0.7541(10) 0.2628(12) 0.0347(19) Uani 0.303(10) 1 d G U P A 1
H17A H 0.276121 0.85768 0.292083 0.042 Uiso 0.303(10) 1 calc R U P A 1
C18A C 0.2766(19) 0.7140(11) 0.1528(11) 0.0333(17) Uani 0.303(10) 1 d G U P A 1
H18A H 0.332162 0.790179 0.107002 0.04 Uiso 0.303(10) 1 calc R U P A 1
C14B C 0.2158(8) 0.5289(6) 0.1227(4) 0.0338(8) Uani 0.697(10) 1 d D U P A 2
C15B C 0.1265(8) 0.4423(5) 0.2022(5) 0.0378(7) Uani 0.697(10) 1 d . U P A 2
H15B H 0.07741 0.334214 0.185991 0.045 Uiso 0.697(10) 1 calc R U P A 2
C16B C 0.1104(8) 0.5156(6) 0.3047(5) 0.0374(8) Uani 0.697(10) 1 d . U P A 2
H16B H 0.047536 0.454249 0.356903 0.045 Uiso 0.697(10) 1 calc R U P A 2
N2B N 0.1761(9) 0.6654(6) 0.3355(5) 0.0395(9) Uani 0.697(10) 1 d . U P A 2
C17B C 0.2604(9) 0.7453(5) 0.2592(6) 0.0397(9) Uani 0.697(10) 1 d . U P A 2
H17B H 0.309495 0.853166 0.279153 0.048 Uiso 0.697(10) 1 calc R U P A 2
C18B C 0.2831(8) 0.6859(6) 0.1536(5) 0.0357(8) Uani 0.697(10) 1 d . U P A 2
H18B H 0.343905 0.75115 0.102486 0.043 Uiso 0.697(10) 1 calc R U P A 2
C19 C 0.2519(8) 0.4118(6) -0.0792(5) 0.0381(8) Uani 0.697(10) 1 d D U P A 2
C20 C 0.2348(4) 0.4630(5) 0.0148(3) 0.0388(6) Uani 0.697(10) 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   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 1.3590(11) . ?
O1 H1 0.84 . ?
O2 C3 1.3559(12) . ?
O2 H2A 0.84 . ?
N1 C7 1.3346(13) . ?
N1 C11 1.3369(14) . ?
C1 C2 1.3907(13) . ?
C1 C6 1.3913(13) . ?
C2 C3 1.3945(13) . ?
C2 H2 0.95 . ?
C3 C4 1.3931(13) . ?
C4 C5 1.3831(16) . ?
C4 H4 0.95 . ?
C5 C6 1.3866(15) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.3804(13) . ?
C7 H7 0.95 . ?
C8 C9 1.3922(13) . ?
C8 H8 0.95 . ?
C9 C10 1.3918(14) . ?
C9 C19 1.399(5) . ?
C9 C12 1.559(10) . ?
C10 C11 1.3766(15) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
C12 C13 1.306(11) . ?
C12 H12 0.95 . ?
C13 C14A 1.529(8) . ?
C13 H13 0.95 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.95 . ?
C16A N2A 1.39 . ?
C16A H16A 0.95 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.95 . ?
C18A H18A 0.95 . ?
C14B C18B 1.388(3) . ?
C14B C15B 1.395(4) . ?
C14B C20 1.406(4) . ?
C15B C16B 1.379(4) . ?
C15B H15B 0.95 . ?
C16B N2B 1.323(3) . ?
C16B H16B 0.95 . ?
N2B C17B 1.319(3) . ?
C17B C18B 1.372(3) . ?
C17B H17B 0.95 . ?
C18B H18B 0.95 . ?
C19 C20 1.198(6) . ?

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 . . ?
C7 N1 C11 117.10(8) . . ?
O1 C1 C2 121.72(8) . . ?
O1 C1 C6 118.30(9) . . ?
C2 C1 C6 119.98(9) . . ?
C1 C2 C3 120.23(8) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
O2 C3 C4 117.93(9) . . ?
O2 C3 C2 122.04(8) . . ?
C4 C3 C2 120.03(9) . . ?
C5 C4 C3 118.86(9) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.87(9) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.01(9) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.37(9) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.12(9) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 117.73(9) . . ?
C10 C9 C19 116.9(2) . . ?
C8 C9 C19 125.3(2) . . ?
C10 C9 C12 129.5(3) . . ?
C8 C9 C12 112.5(3) . . ?
C11 C10 C9 118.81(9) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.83(9) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13 C12 C9 122.7(8) . . ?
C13 C12 H12 118.7 . . ?
C9 C12 H12 118.7 . . ?
C12 C13 C14A 127.5(8) . . ?
C12 C13 H13 116.2 . . ?
C14A C13 H13 116.2 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13 119.8(5) . . ?
C18A C14A C13 120.2(5) . . ?
C16A C15A C14A 120 . . ?
C16A C15A H15A 120 . . ?
C14A C15A H15A 120 . . ?
C15A C16A N2A 120 . . ?
C15A C16A H16A 120 . . ?
N2A C16A H16A 120 . . ?
C16A N2A C17A 120 . . ?
C18A C17A N2A 120 . . ?
C18A C17A H17A 120 . . ?
N2A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C15B 116.52(19) . . ?
C18B C14B C20 120.8(3) . . ?
C15B C14B C20 122.7(3) . . ?
C16B C15B C14B 119.1(2) . . ?
C16B C15B H15B 120.5 . . ?
C14B C15B H15B 120.5 . . ?
N2B C16B C15B 124.7(2) . . ?
N2B C16B H16B 117.7 . . ?
C15B C16B H16B 117.7 . . ?
C17B N2B C16B 115.3(2) . . ?
N2B C17B C18B 125.6(2) . . ?
N2B C17B H17B 117.2 . . ?
C18B C17B H17B 117.2 . . ?
C17B C18B C14B 118.83(19) . . ?
C17B C18B H18B 120.6 . . ?
C14B C18B H18B 120.6 . . ?
C20 C19 C9 175.5(5) . . ?
C19 C20 C14B 177.4(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 -179.59(8) . . . . ?
C6 C1 C2 C3 0.62(13) . . . . ?
C1 C2 C3 O2 178.36(8) . . . . ?
C1 C2 C3 C4 -1.41(14) . . . . ?
O2 C3 C4 C5 -178.51(9) . . . . ?
C2 C3 C4 C5 1.27(14) . . . . ?
C3 C4 C5 C6 -0.36(16) . . . . ?
C4 C5 C6 C1 -0.42(15) . . . . ?
O1 C1 C6 C5 -179.51(8) . . . . ?
C2 C1 C6 C5 0.29(14) . . . . ?
C11 N1 C7 C8 1.66(15) . . . . ?
N1 C7 C8 C9 -0.70(15) . . . . ?
C7 C8 C9 C10 -1.12(14) . . . . ?
C7 C8 C9 C19 177.6(3) . . . . ?
C7 C8 C9 C12 174.1(5) . . . . ?
C8 C9 C10 C11 1.91(14) . . . . ?
C19 C9 C10 C11 -176.9(3) . . . . ?
C12 C9 C10 C11 -172.4(6) . . . . ?
C7 N1 C11 C10 -0.79(15) . . . . ?
C9 C10 C11 N1 -1.00(15) . . . . ?
C10 C9 C12 C13 -3.8(14) . . . . ?
C8 C9 C12 C13 -178.4(8) . . . . ?
C9 C12 C13 C14A 177.1(8) . . . . ?
C12 C13 C14A C15A 4.2(12) . . . . ?
C12 C13 C14A C18A -175.9(9) . . . . ?
C18A C14A C15A C16A 0 . . . . ?
C13 C14A C15A C16A 179.8(10) . . . . ?
C14A C15A C16A N2A 0 . . . . ?
C15A C16A N2A C17A 0 . . . . ?
C16A N2A C17A C18A 0 . . . . ?
N2A C17A C18A C14A 0 . . . . ?
C15A C14A C18A C17A 0 . . . . ?
C13 C14A C18A C17A -179.8(10) . . . . ?
C18B C14B C15B C16B 0.0(3) . . . . ?
C20 C14B C15B C16B -178.8(5) . . . . ?
C14B C15B C16B N2B -0.8(3) . . . . ?
C15B C16B N2B C17B 0.7(3) . . . . ?
C16B N2B C17B C18B 0.2(3) . . . . ?
N2B C17B C18B C14B -1.0(3) . . . . ?
C15B C14B C18B C17B 0.8(3) . . . . ?
C20 C14B C18B C17B 179.6(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 0.84 1.91 2.7452(11) 174.6 1_556 yes
O2 H2A N2A^a 0.84 1.98 2.82(5) 174.7 2_666 yes
O2 H2A N2B^b 0.84 1.89 2.725(4) 176.7 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_BE25_BA75_230
_database_code_depnum_ccdc_archive 'CCDC 1995689'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

_audit_creation_date             2020-04-02T10:35:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C18 H14.60 N2 O2'
_chemical_formula_weight         290.92

#----------------------------------------------------------------------------#
#                   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                   8.18873(15)
_cell_length_b                   9.82362(13)
_cell_length_c                   10.94583(15)
_cell_angle_alpha                92.3016(11)
_cell_angle_beta                 108.0971(14)
_cell_angle_gamma                114.5370(15)
_cell_volume                     746.66(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    10371
_cell_measurement_theta_min      4.32
_cell_measurement_theta_max      76.857

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

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.082
_exptl_crystal_density_diffrn    1.294
_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
-2 6 -1 0.0431
5 -4 -4 0.0754
5 0 0 0.0393
1 -5 5 0.0478
0 -3 -5 0.0753
0 3 -6 0.0824
-5 0 0 0.0431
2 -6 2 0.0449
2 4 -1 0.0344
-3 -3 5 0.0681
5 -4 1 0.0424
3 -4 4 0.0384
3 0 4 0.0674
-3 -1 -4 0.0729
-1 1 7 0.0918
-1 -2 7 0.0812
3 -4 -5 0.0856
0 5 -4 0.0552

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

_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.92785
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.869
_shelx_estimated_absorpt_T_max   0.945

#----------------------------------------------------------------------------#
#                   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      -0.1815738
_diffrn_orient_matrix_ub_12      -0.0492899
_diffrn_orient_matrix_ub_13      0.035555
_diffrn_orient_matrix_ub_21      0.1269789
_diffrn_orient_matrix_ub_22      0.0760229
_diffrn_orient_matrix_ub_23      0.1442877
_diffrn_orient_matrix_ub_31      -0.0069873
_diffrn_orient_matrix_ub_32      0.1506386
_diffrn_orient_matrix_ub_33      -0.0267159
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_number            14756
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_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         77.376
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.971
_reflns_Friedel_coverage         0
_reflns_number_total             3088
_reflns_number_gt                2778
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_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)+(0.0490P)²+0.0627P] 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       0.0036(7)
_refine_ls_number_reflns         3088
_refine_ls_number_parameters     265
_refine_ls_number_restraints     438
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0959
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.13
_refine_diff_density_rms         0.029

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

_refine_special_details          
;
 To help model the substitution of the bis(4-pyridyl)acetylene with 
 1,2-bis(4-pyridyl)ethylene, the atom sites N2 and  C14 < C18, were split into
 parts A and B. These sites along with C12, C13 (BPE), C19 and C20 (BPA) 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 BPA to BPE was 0.30
 to 0.70.
;

#----------------------------------------------------------------------------#
#                   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 0.16768(10) 0.14685(8) 0.30450(7) 0.0492(2) Uani 1 1 d . . . . .
H1 H 0.200832 0.172565 0.384905 0.074 Uiso 1 1 calc R U . . .
O2 O 0.81816(11) 0.21569(10) 0.43316(7) 0.0566(2) Uani 1 1 d . . . . .
H2A H 0.823178 0.251167 0.505085 0.085 Uiso 1 1 calc R U . . .
N1 N 0.26264(13) 0.24228(11) -0.43244(8) 0.0503(2) Uani 1 1 d . . . . .
C1 C 0.31783(14) 0.14680(10) 0.27605(9) 0.0405(2) Uani 1 1 d . . . . .
C2 C 0.49251(14) 0.18009(10) 0.37364(9) 0.0408(2) Uani 1 1 d . . . . .
H2 H 0.508586 0.202583 0.462122 0.049 Uiso 1 1 calc R U . . .
C3 C 0.64402(15) 0.18030(11) 0.34098(9) 0.0437(2) Uani 1 1 d . . . . .
C4 C 0.61903(17) 0.14336(12) 0.21024(10) 0.0516(3) Uani 1 1 d . . . . .
H4 H 0.719508 0.140943 0.187396 0.062 Uiso 1 1 calc R U . . .
C5 C 0.44425(18) 0.11032(13) 0.11467(10) 0.0551(3) Uani 1 1 d . . . . .
H5 H 0.427317 0.086071 0.026234 0.066 Uiso 1 1 calc R U . . .
C6 C 0.29309(16) 0.11188(12) 0.14531(10) 0.0501(3) Uani 1 1 d . . . . .
H6 H 0.175494 0.089633 0.078621 0.06 Uiso 1 1 calc R U . . .
C7 C 0.19750(15) 0.14709(12) -0.35635(10) 0.0490(2) Uani 1 1 d . . . . .
H7 H 0.15385 0.04225 -0.384473 0.059 Uiso 1 1 calc R U . . .
C8 C 0.19091(15) 0.19453(11) -0.23867(10) 0.0465(2) Uani 1 1 d . . . . .
H8 H 0.142596 0.123151 -0.188606 0.056 Uiso 1 1 calc R U . . .
C9 C 0.25651(13) 0.34916(11) -0.19478(9) 0.0424(2) Uani 1 1 d D . . . .
C10 C 0.32965(15) 0.44939(12) -0.27178(11) 0.0489(2) Uani 1 1 d . . . . .
H10 H 0.379246 0.555195 -0.244496 0.059 Uiso 1 1 calc R U . . .
C11 C 0.32820(16) 0.39104(13) -0.38868(11) 0.0523(3) Uani 1 1 d . . . . .
H11 H 0.376054 0.459722 -0.440741 0.063 Uiso 1 1 calc R U . . .
C12 C 0.221(2) 0.3821(11) -0.0670(12) 0.0361(15) Uani 0.300(10) 1 d D U P A 1
H12 H 0.164471 0.299013 -0.029121 0.043 Uiso 0.300(10) 1 calc R U P A 1
C13 C 0.2635(8) 0.5154(9) -0.0110(6) 0.0380(11) Uani 0.300(10) 1 d D U P A 1
H13 H 0.324217 0.596108 -0.049545 0.046 Uiso 0.300(10) 1 calc R U P A 1
C14A C 0.2288(19) 0.5612(12) 0.1111(10) 0.0379(18) Uani 0.300(10) 1 d DG U P A
1
C15A C 0.148(2) 0.4499(10) 0.1779(11) 0.044(2) Uani 0.300(10) 1 d G U P A 1
H15A H 0.116874 0.347675 0.149001 0.053 Uiso 0.300(10) 1 calc R U P A 1
C16A C 0.1141(19) 0.4896(13) 0.2876(11) 0.043(2) Uani 0.300(10) 1 d G U P A 1
H16A H 0.059648 0.414308 0.332771 0.052 Uiso 0.300(10) 1 calc R U P A 1
N2A N 0.161(2) 0.6407(14) 0.3303(11) 0.0394(18) Uani 0.300(10) 1 d G U P A 1
C17A C 0.241(2) 0.7521(11) 0.2635(13) 0.043(2) Uani 0.300(10) 1 d G U P A 1
H17A H 0.272418 0.854243 0.292382 0.052 Uiso 0.300(10) 1 calc R U P A 1
C18A C 0.275(2) 0.7123(11) 0.1538(12) 0.0408(18) Uani 0.300(10) 1 d G U P A 1
H18A H 0.329646 0.787613 0.108611 0.049 Uiso 0.300(10) 1 calc R U P A 1
C14B C 0.2150(9) 0.5278(6) 0.1220(5) 0.0408(8) Uani 0.700(10) 1 d D U P A 2
C15B C 0.1267(9) 0.4421(5) 0.2017(5) 0.0450(8) Uani 0.700(10) 1 d . U P A 2
H15B H 0.077852 0.335367 0.185727 0.054 Uiso 0.700(10) 1 calc R U P A 2
C16B C 0.1118(9) 0.5162(6) 0.3044(5) 0.0441(9) Uani 0.700(10) 1 d . U P A 2
H16B H 0.05034 0.456007 0.356314 0.053 Uiso 0.700(10) 1 calc R U P A 2
N2B N 0.1776(9) 0.6654(6) 0.3352(5) 0.0460(9) Uani 0.700(10) 1 d . U P A 2
C17B C 0.2615(9) 0.7447(5) 0.2591(6) 0.0472(9) Uani 0.700(10) 1 d . U P A 2
H17B H 0.310888 0.851381 0.279043 0.057 Uiso 0.700(10) 1 calc R U P A 2
C18B C 0.2827(8) 0.6844(6) 0.1531(5) 0.0437(9) Uani 0.700(10) 1 d . U P A 2
H18B H 0.34219 0.748277 0.102316 0.052 Uiso 0.700(10) 1 calc R U P A 2
C19 C 0.2519(9) 0.4127(7) -0.0799(6) 0.0462(9) Uani 0.700(10) 1 d D U P A 2
C20 C 0.2340(4) 0.4618(5) 0.0146(3) 0.0464(6) Uani 0.700(10) 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   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(12) . ?
O1 H1 0.83 . ?
O2 C3 1.3559(12) . ?
O2 H2A 0.83 . ?
N1 C7 1.3331(14) . ?
N1 C11 1.3363(14) . ?
C1 C2 1.3886(14) . ?
C1 C6 1.3890(13) . ?
C2 C3 1.3931(14) . ?
C2 H2 0.94 . ?
C3 C4 1.3914(14) . ?
C4 C5 1.3802(17) . ?
C4 H4 0.94 . ?
C5 C6 1.3850(16) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3767(14) . ?
C7 H7 0.94 . ?
C8 C9 1.3893(14) . ?
C8 H8 0.94 . ?
C9 C10 1.3889(15) . ?
C9 C19 1.399(5) . ?
C9 C12 1.563(11) . ?
C10 C11 1.3755(15) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.279(12) . ?
C12 H12 0.94 . ?
C13 C14A 1.537(9) . ?
C13 H13 0.94 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.94 . ?
C16A N2A 1.39 . ?
C16A H16A 0.94 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.94 . ?
C18A H18A 0.94 . ?
C14B C18B 1.386(4) . ?
C14B C15B 1.392(4) . ?
C14B C20 1.401(4) . ?
C15B C16B 1.378(4) . ?
C15B H15B 0.94 . ?
C16B N2B 1.321(4) . ?
C16B H16B 0.94 . ?
N2B C17B 1.318(3) . ?
C17B C18B 1.372(3) . ?
C17B H17B 0.94 . ?
C18B H18B 0.94 . ?
C19 C20 1.199(6) . ?

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 . . ?
C7 N1 C11 117.12(9) . . ?
O1 C1 C2 121.78(8) . . ?
O1 C1 C6 118.28(9) . . ?
C2 C1 C6 119.94(9) . . ?
C1 C2 C3 120.29(9) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
O2 C3 C4 117.96(9) . . ?
O2 C3 C2 122.08(9) . . ?
C4 C3 C2 119.95(10) . . ?
C5 C4 C3 118.89(10) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.89(9) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.02(10) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.33(9) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.21(9) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 117.76(9) . . ?
C10 C9 C19 116.9(3) . . ?
C8 C9 C19 125.3(2) . . ?
C10 C9 C12 129.4(4) . . ?
C8 C9 C12 112.7(3) . . ?
C11 C10 C9 118.81(10) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.74(10) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13 C12 C9 123.8(9) . . ?
C13 C12 H12 118.1 . . ?
C9 C12 H12 118.1 . . ?
C12 C13 C14A 128.6(9) . . ?
C12 C13 H13 115.7 . . ?
C14A C13 H13 115.7 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13 119.5(6) . . ?
C18A C14A C13 120.5(6) . . ?
C16A C15A C14A 120 . . ?
C16A C15A H15A 120 . . ?
C14A C15A H15A 120 . . ?
N2A C16A C15A 120 . . ?
N2A C16A H16A 120 . . ?
C15A C16A H16A 120 . . ?
C17A N2A C16A 120 . . ?
N2A C17A C18A 120 . . ?
N2A C17A H17A 120 . . ?
C18A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C15B 116.4(2) . . ?
C18B C14B C20 120.8(3) . . ?
C15B C14B C20 122.8(3) . . ?
C16B C15B C14B 119.0(2) . . ?
C16B C15B H15B 120.5 . . ?
C14B C15B H15B 120.5 . . ?
N2B C16B C15B 124.8(2) . . ?
N2B C16B H16B 117.6 . . ?
C15B C16B H16B 117.6 . . ?
C17B N2B C16B 115.3(2) . . ?
N2B C17B C18B 125.3(2) . . ?
N2B C17B H17B 117.4 . . ?
C18B C17B H17B 117.4 . . ?
C17B C18B C14B 119.10(19) . . ?
C17B C18B H18B 120.5 . . ?
C14B C18B H18B 120.5 . . ?
C20 C19 C9 175.3(6) . . ?
C19 C20 C14B 176.4(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 -179.45(8) . . . . ?
C6 C1 C2 C3 0.71(14) . . . . ?
C1 C2 C3 O2 178.42(8) . . . . ?
C1 C2 C3 C4 -1.58(14) . . . . ?
O2 C3 C4 C5 -178.56(10) . . . . ?
C2 C3 C4 C5 1.45(15) . . . . ?
C3 C4 C5 C6 -0.47(17) . . . . ?
C4 C5 C6 C1 -0.40(16) . . . . ?
O1 C1 C6 C5 -179.57(9) . . . . ?
C2 C1 C6 C5 0.27(14) . . . . ?
C11 N1 C7 C8 1.60(16) . . . . ?
N1 C7 C8 C9 -0.62(16) . . . . ?
C7 C8 C9 C10 -1.20(15) . . . . ?
C7 C8 C9 C19 177.6(3) . . . . ?
C7 C8 C9 C12 174.4(6) . . . . ?
C8 C9 C10 C11 1.98(15) . . . . ?
C19 C9 C10 C11 -176.9(3) . . . . ?
C12 C9 C10 C11 -172.8(7) . . . . ?
C7 N1 C11 C10 -0.75(16) . . . . ?
C9 C10 C11 N1 -1.04(17) . . . . ?
C10 C9 C12 C13 -2.7(17) . . . . ?
C8 C9 C12 C13 -177.7(10) . . . . ?
C9 C12 C13 C14A 177.5(9) . . . . ?
C12 C13 C14A C15A 3.1(14) . . . . ?
C12 C13 C14A C18A -176.2(11) . . . . ?
C18A C14A C15A C16A 0 . . . . ?
C13 C14A C15A C16A -179.3(11) . . . . ?
C14A C15A C16A N2A 0 . . . . ?
C15A C16A N2A C17A 0 . . . . ?
C16A N2A C17A C18A 0 . . . . ?
N2A C17A C18A C14A 0 . . . . ?
C15A C14A C18A C17A 0 . . . . ?
C13 C14A C18A C17A 179.3(11) . . . . ?
C18B C14B C15B C16B 0.0(3) . . . . ?
C20 C14B C15B C16B -179.2(5) . . . . ?
C14B C15B C16B N2B -0.7(3) . . . . ?
C15B C16B N2B C17B 0.4(3) . . . . ?
C16B N2B C17B C18B 0.5(3) . . . . ?
N2B C17B C18B C14B -1.2(4) . . . . ?
C15B C14B C18B C17B 0.8(3) . . . . ?
C20 C14B C18B C17B -180.0(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 1.92 2.7498(11) 174.5 1_556 yes
O2 H2A N2A^a 0.83 1.99 2.82(6) 173.1 2_666 yes
O2 H2A N2B^b 0.83 1.9 2.733(4) 176.7 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_BE25_BA75_250
_database_code_depnum_ccdc_archive 'CCDC 1995690'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

_audit_creation_date             2020-04-02T10:38:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C18 H14.58 N2 O2'
_chemical_formula_weight         290.9

#----------------------------------------------------------------------------#
#                   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                   8.20354(16)
_cell_length_b                   9.82973(15)
_cell_length_c                   10.95062(15)
_cell_angle_alpha                92.3825(12)
_cell_angle_beta                 108.0580(14)
_cell_angle_gamma                114.4899(17)
_cell_volume                     749.11(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    10087
_cell_measurement_theta_min      4.314
_cell_measurement_theta_max      77.123

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

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.082
_exptl_crystal_density_diffrn    1.29
_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
-2 6 -1 0.0431
5 -4 -4 0.0754
5 0 0 0.0393
1 -5 5 0.0478
0 -3 -5 0.0753
0 3 -6 0.0824
-5 0 0 0.0431
2 -6 2 0.0449
2 4 -1 0.0344
-3 -3 5 0.0681
5 -4 1 0.0424
3 -4 4 0.0384
3 0 4 0.0674
-3 -1 -4 0.0729
-1 1 7 0.0918
-1 -2 7 0.0812
3 -4 -5 0.0856
0 5 -4 0.0552

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

_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.90605
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.869
_shelx_estimated_absorpt_T_max   0.946

#----------------------------------------------------------------------------#
#                   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      -0.1810864
_diffrn_orient_matrix_ub_12      -0.0489953
_diffrn_orient_matrix_ub_13      0.0356887
_diffrn_orient_matrix_ub_21      0.1268521
_diffrn_orient_matrix_ub_22      0.0761251
_diffrn_orient_matrix_ub_23      0.1441907
_diffrn_orient_matrix_ub_31      -0.0069403
_diffrn_orient_matrix_ub_32      0.1504868
_diffrn_orient_matrix_ub_33      -0.0266988
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_number            14771
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.331
_diffrn_reflns_theta_max         77.402
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.971
_reflns_Friedel_coverage         0
_reflns_number_total             3099
_reflns_number_gt                2750
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_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)+(0.0510P)²+0.0519P] 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         3099
_refine_ls_number_parameters     265
_refine_ls_number_restraints     438
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.029

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

_refine_special_details          
;
 To help model the substitution of the bis(4-pyridyl)acetylene with 
 1,2-bis(4-pyridyl)ethylene, the atom sites N2 and  C14 < C18, were split into
 parts A and B. These sites along with C12, C13 (BPE), C19 and C20 (BPA) 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 BPA to BPE was 0.29
 to 0.71.
;

#----------------------------------------------------------------------------#
#                   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 0.16828(10) 0.14646(9) 0.30450(7) 0.0538(2) Uani 1 1 d . . . . .
H1 H 0.201072 0.171628 0.38492 0.081 Uiso 1 1 calc R U . . .
O2 O 0.81743(11) 0.21572(10) 0.43280(8) 0.0620(2) Uani 1 1 d . . . . .
H2A H 0.822066 0.250374 0.504883 0.093 Uiso 1 1 calc R U . . .
N1 N 0.26257(13) 0.24192(11) -0.43241(8) 0.0545(2) Uani 1 1 d . . . . .
C1 C 0.31818(14) 0.14648(10) 0.27607(9) 0.0440(2) Uani 1 1 d . . . . .
C2 C 0.49240(14) 0.17984(10) 0.37331(9) 0.0443(2) Uani 1 1 d . . . . .
H2 H 0.508463 0.202411 0.461764 0.053 Uiso 1 1 calc R U . . .
C3 C 0.64354(15) 0.18011(11) 0.34080(10) 0.0475(2) Uani 1 1 d . . . . .
C4 C 0.61868(17) 0.14337(12) 0.21009(11) 0.0560(3) Uani 1 1 d . . . . .
H4 H 0.719017 0.141081 0.187205 0.067 Uiso 1 1 calc R U . . .
C5 C 0.44447(19) 0.11039(13) 0.11465(10) 0.0599(3) Uani 1 1 d . . . . .
H5 H 0.427655 0.086324 0.026229 0.072 Uiso 1 1 calc R U . . .
C6 C 0.29373(17) 0.11172(12) 0.14543(10) 0.0545(3) Uani 1 1 d . . . . .
H6 H 0.176351 0.089399 0.078802 0.065 Uiso 1 1 calc R U . . .
C7 C 0.19747(16) 0.14725(12) -0.35629(10) 0.0533(3) Uani 1 1 d . . . . .
H7 H 0.153672 0.042415 -0.384319 0.064 Uiso 1 1 calc R U . . .
C8 C 0.19105(15) 0.19508(12) -0.23870(10) 0.0503(2) Uani 1 1 d . . . . .
H8 H 0.142851 0.12399 -0.188554 0.06 Uiso 1 1 calc R U . . .
C9 C 0.25658(13) 0.34949(11) -0.19507(9) 0.0457(2) Uani 1 1 d D . . . .
C10 C 0.32965(16) 0.44931(12) -0.27208(11) 0.0530(3) Uani 1 1 d . . . . .
H10 H 0.379265 0.555083 -0.244923 0.064 Uiso 1 1 calc R U . . .
C11 C 0.32808(16) 0.39059(13) -0.38866(11) 0.0567(3) Uani 1 1 d . . . . .
H11 H 0.375906 0.459018 -0.440756 0.068 Uiso 1 1 calc R U . . .
C12 C 0.221(2) 0.3822(11) -0.0680(13) 0.0405(16) Uani 0.291(11) 1 d D U P A 1
H12 H 0.16367 0.298755 -0.030891 0.049 Uiso 0.291(11) 1 calc R U P A 1
C13 C 0.2634(8) 0.5150(9) -0.0108(7) 0.0405(12) Uani 0.291(11) 1 d D U P A 1
H13 H 0.32562 0.595984 -0.048287 0.049 Uiso 0.291(11) 1 calc R U P A 1
C14A C 0.228(2) 0.5607(13) 0.1100(10) 0.0407(19) Uani 0.291(11) 1 d DG U P A 1
C15A C 0.148(2) 0.4500(11) 0.1774(12) 0.047(2) Uani 0.291(11) 1 d G U P A 1
H15A H 0.116063 0.34772 0.14857 0.056 Uiso 0.291(11) 1 calc R U P A 1
C16A C 0.115(2) 0.4906(13) 0.2875(11) 0.046(2) Uani 0.291(11) 1 d G U P A 1
H16A H 0.061485 0.415822 0.333101 0.056 Uiso 0.291(11) 1 calc R U P A 1
N2A N 0.163(2) 0.6419(15) 0.3302(11) 0.043(2) Uani 0.291(11) 1 d G U P A 1
C17A C 0.242(2) 0.7526(11) 0.2628(12) 0.046(2) Uani 0.291(11) 1 d G U P A 1
H17A H 0.274304 0.854864 0.291648 0.055 Uiso 0.291(11) 1 calc R U P A 1
C18A C 0.275(2) 0.7119(12) 0.1527(12) 0.046(2) Uani 0.291(11) 1 d G U P A 1
H18A H 0.328884 0.786766 0.107116 0.056 Uiso 0.291(11) 1 calc R U P A 1
C14B C 0.2151(8) 0.5275(6) 0.1223(4) 0.0441(9) Uani 0.709(11) 1 d D U P A 2
C15B C 0.1271(9) 0.4419(5) 0.2020(5) 0.0487(8) Uani 0.709(11) 1 d . U P A 2
H15B H 0.078714 0.335269 0.186013 0.058 Uiso 0.709(11) 1 calc R U P A 2
C16B C 0.1119(9) 0.5155(6) 0.3045(5) 0.0485(9) Uani 0.709(11) 1 d . U P A 2
H16B H 0.050369 0.455217 0.356203 0.058 Uiso 0.709(11) 1 calc R U P A 2
N2B N 0.1774(9) 0.6645(6) 0.3355(5) 0.0510(10) Uani 0.709(11) 1 d . U P A 2
C17B C 0.2610(9) 0.7436(5) 0.2594(6) 0.0529(10) Uani 0.709(11) 1 d . U P A 2
H17B H 0.31041 0.850145 0.279539 0.064 Uiso 0.709(11) 1 calc R U P A 2
C18B C 0.2820(8) 0.6838(6) 0.1535(5) 0.0477(8) Uani 0.709(11) 1 d . U P A 2
H18B H 0.340965 0.747762 0.102588 0.057 Uiso 0.709(11) 1 calc R U P A 2
C19 C 0.2517(9) 0.4132(7) -0.0798(6) 0.0513(10) Uani 0.709(11) 1 d D U P A 2
C20 C 0.2335(4) 0.4610(5) 0.0143(3) 0.0511(7) Uani 0.709(11) 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   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 1.3588(12) . ?
O1 H1 0.83 . ?
O2 C3 1.3558(13) . ?
O2 H2A 0.83 . ?
N1 C7 1.3322(15) . ?
N1 C11 1.3360(15) . ?
C1 C2 1.3867(14) . ?
C1 C6 1.3886(14) . ?
C2 C3 1.3910(14) . ?
C2 H2 0.94 . ?
C3 C4 1.3914(14) . ?
C4 C5 1.3789(17) . ?
C4 H4 0.94 . ?
C5 C6 1.3836(17) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3762(14) . ?
C7 H7 0.94 . ?
C8 C9 1.3874(14) . ?
C8 H8 0.94 . ?
C9 C10 1.3885(15) . ?
C9 C19 1.405(5) . ?
C9 C12 1.556(12) . ?
C10 C11 1.3731(16) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.279(12) . ?
C12 H12 0.94 . ?
C13 C14A 1.528(9) . ?
C13 H13 0.94 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.94 . ?
C16A N2A 1.39 . ?
C16A H16A 0.94 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.94 . ?
C18A H18A 0.94 . ?
C14B C18B 1.385(4) . ?
C14B C15B 1.392(4) . ?
C14B C20 1.407(4) . ?
C15B C16B 1.375(4) . ?
C15B H15B 0.94 . ?
C16B N2B 1.320(3) . ?
C16B H16B 0.94 . ?
N2B C17B 1.318(3) . ?
C17B C18B 1.368(3) . ?
C17B H17B 0.94 . ?
C18B H18B 0.94 . ?
C19 C20 1.190(6) . ?

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 . . ?
C7 N1 C11 117.01(9) . . ?
O1 C1 C2 121.88(8) . . ?
O1 C1 C6 118.29(9) . . ?
C2 C1 C6 119.83(10) . . ?
C1 C2 C3 120.43(9) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.20(9) . . ?
O2 C3 C4 117.93(9) . . ?
C2 C3 C4 119.87(10) . . ?
C5 C4 C3 118.93(10) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.83(10) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.10(10) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N1 C7 C8 123.36(10) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.20(10) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C10 117.79(9) . . ?
C8 C9 C19 125.1(3) . . ?
C10 C9 C19 117.1(3) . . ?
C8 C9 C12 112.5(4) . . ?
C10 C9 C12 129.6(4) . . ?
C11 C10 C9 118.75(10) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.85(10) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13 C12 C9 124.3(10) . . ?
C13 C12 H12 117.8 . . ?
C9 C12 H12 117.8 . . ?
C12 C13 C14A 129.2(10) . . ?
C12 C13 H13 115.4 . . ?
C14A C13 H13 115.4 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13 119.6(6) . . ?
C18A C14A C13 120.4(6) . . ?
C14A C15A C16A 120 . . ?
C14A C15A H15A 120 . . ?
C16A C15A H15A 120 . . ?
N2A C16A C15A 120 . . ?
N2A C16A H16A 120 . . ?
C15A C16A H16A 120 . . ?
C17A N2A C16A 120 . . ?
N2A C17A C18A 120 . . ?
N2A C17A H17A 120 . . ?
C18A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C15B 116.4(2) . . ?
C18B C14B C20 120.9(3) . . ?
C15B C14B C20 122.7(3) . . ?
C16B C15B C14B 119.1(2) . . ?
C16B C15B H15B 120.4 . . ?
C14B C15B H15B 120.4 . . ?
N2B C16B C15B 124.8(2) . . ?
N2B C16B H16B 117.6 . . ?
C15B C16B H16B 117.6 . . ?
C17B N2B C16B 115.2(2) . . ?
N2B C17B C18B 125.5(2) . . ?
N2B C17B H17B 117.2 . . ?
C18B C17B H17B 117.2 . . ?
C17B C18B C14B 119.0(2) . . ?
C17B C18B H18B 120.5 . . ?
C14B C18B H18B 120.5 . . ?
C20 C19 C9 175.3(6) . . ?
C19 C20 C14B 175.8(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 -179.46(8) . . . . ?
C6 C1 C2 C3 0.60(14) . . . . ?
C1 C2 C3 O2 178.37(9) . . . . ?
C1 C2 C3 C4 -1.44(15) . . . . ?
O2 C3 C4 C5 -178.44(10) . . . . ?
C2 C3 C4 C5 1.38(16) . . . . ?
C3 C4 C5 C6 -0.50(17) . . . . ?
C4 C5 C6 C1 -0.33(17) . . . . ?
O1 C1 C6 C5 -179.66(9) . . . . ?
C2 C1 C6 C5 0.28(15) . . . . ?
C11 N1 C7 C8 1.53(16) . . . . ?
N1 C7 C8 C9 -0.55(16) . . . . ?
C7 C8 C9 C10 -1.25(15) . . . . ?
C7 C8 C9 C19 177.5(4) . . . . ?
C7 C8 C9 C12 174.4(7) . . . . ?
C8 C9 C10 C11 1.99(15) . . . . ?
C19 C9 C10 C11 -176.9(3) . . . . ?
C12 C9 C10 C11 -172.7(8) . . . . ?
C7 N1 C11 C10 -0.72(16) . . . . ?
C9 C10 C11 N1 -1.04(17) . . . . ?
C8 C9 C12 C13 -178.1(11) . . . . ?
C10 C9 C12 C13 -3.1(18) . . . . ?
C9 C12 C13 C14A 177.1(10) . . . . ?
C12 C13 C14A C15A 4.2(15) . . . . ?
C12 C13 C14A C18A -175.9(12) . . . . ?
C18A C14A C15A C16A 0 . . . . ?
C13 C14A C15A C16A 179.9(11) . . . . ?
C14A C15A C16A N2A 0 . . . . ?
C15A C16A N2A C17A 0 . . . . ?
C16A N2A C17A C18A 0 . . . . ?
N2A C17A C18A C14A 0 . . . . ?
C15A C14A C18A C17A 0 . . . . ?
C13 C14A C18A C17A -179.9(11) . . . . ?
C18B C14B C15B C16B 0.0(3) . . . . ?
C20 C14B C15B C16B -178.9(5) . . . . ?
C14B C15B C16B N2B -0.8(3) . . . . ?
C15B C16B N2B C17B 0.5(3) . . . . ?
C16B N2B C17B C18B 0.7(3) . . . . ?
N2B C17B C18B C14B -1.5(4) . . . . ?
C15B C14B C18B C17B 1.0(3) . . . . ?
C20 C14B C18B C17B 180.0(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 1.92 2.7515(11) 174.1 1_556 yes
O2 H2A N2A^a 0.83 2 2.82(6) 172.7 2_666 yes
O2 H2A N2B^b 0.83 1.9 2.733(4) 176.3 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_BE25_BA75_290
_database_code_depnum_ccdc_archive 'CCDC 1995692'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

_audit_creation_date             2020-04-02T10:39:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C18 H14.60 N2 O2'
_chemical_formula_weight         290.92

#----------------------------------------------------------------------------#
#                   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                   8.23553(13)
_cell_length_b                   9.85058(13)
_cell_length_c                   10.96006(14)
_cell_angle_alpha                92.5489(11)
_cell_angle_beta                 107.9571(13)
_cell_angle_gamma                114.4335(14)
_cell_volume                     754.73(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    9266
_cell_measurement_theta_min      4.309
_cell_measurement_theta_max      77.052

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

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.082
_exptl_crystal_density_diffrn    1.28
_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
5 0 0 0.0393
-5 0 0 0.0431
3 -4 -5 0.0856
2 -6 2 0.0449
1 -5 5 0.0478
-1 -2 7 0.0812
-2 6 -1 0.0431
0 3 -6 0.0824
0 5 -4 0.0552
5 -4 -4 0.0754
-3 -3 5 0.0681
2 4 -1 0.0344
5 -4 1 0.0424
3 0 4 0.0674
3 -4 4 0.0384
-3 -1 -4 0.0729
-1 1 7 0.0918
0 -3 -5 0.0753

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

_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.8615
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.87
_shelx_estimated_absorpt_T_max   0.946

#----------------------------------------------------------------------------#
#                   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      -0.1801461
_diffrn_orient_matrix_ub_12      -0.0484094
_diffrn_orient_matrix_ub_13      0.0358314
_diffrn_orient_matrix_ub_21      0.1263725
_diffrn_orient_matrix_ub_22      0.0763639
_diffrn_orient_matrix_ub_23      0.1439825
_diffrn_orient_matrix_ub_31      -0.0067914
_diffrn_orient_matrix_ub_32      0.1501464
_diffrn_orient_matrix_ub_33      -0.0267269
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_number            14795
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.327
_diffrn_reflns_theta_max         77.252
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.969
_reflns_Friedel_coverage         0
_reflns_number_total             3117
_reflns_number_gt                2722
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_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)+(0.0530P)²+0.0536P] 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(8)
_refine_ls_number_reflns         3117
_refine_ls_number_parameters     265
_refine_ls_number_restraints     438
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.1034
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.028

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

_refine_special_details          
;
 To help model the substitution of the bis(4-pyridyl)acetylene with 
 1,2-bis(4-pyridyl)ethylene, the atom sites N2 and  C14 < C18, were split into
 parts A and B. These sites along with C12, C13 (BPE), C19 and C20 (BPA) 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 BPA to BPE was 0.30
 to 0.70.
;

#----------------------------------------------------------------------------#
#                   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 0.16928(11) 0.14547(9) 0.30455(8) 0.0637(2) Uani 1 1 d . . . . .
H1 H 0.200471 0.168266 0.384046 0.096 Uiso 1 1 calc R U . . .
O2 O 0.81576(12) 0.21562(11) 0.43213(8) 0.0734(3) Uani 1 1 d . . . . .
H2A H 0.819923 0.24911 0.503465 0.11 Uiso 1 1 calc R U . . .
N1 N 0.26237(14) 0.24129(12) -0.43228(9) 0.0637(3) Uani 1 1 d . . . . .
C1 C 0.31911(15) 0.14580(11) 0.27618(10) 0.0514(2) Uani 1 1 d . . . . .
C2 C 0.49213(15) 0.17924(11) 0.37302(10) 0.0516(2) Uani 1 1 d . . . . .
H2 H 0.507828 0.201411 0.460481 0.062 Uiso 1 1 calc R U . . .
C3 C 0.64266(16) 0.17989(12) 0.34037(10) 0.0558(3) Uani 1 1 d . . . . .
C4 C 0.61805(19) 0.14360(13) 0.20989(12) 0.0658(3) Uani 1 1 d . . . . .
H4 H 0.717084 0.141818 0.187108 0.079 Uiso 1 1 calc R U . . .
C5 C 0.4451(2) 0.11039(14) 0.11506(11) 0.0701(3) Uani 1 1 d . . . . .
H5 H 0.428668 0.086607 0.027643 0.084 Uiso 1 1 calc R U . . .
C6 C 0.29496(18) 0.11132(13) 0.14585(11) 0.0637(3) Uani 1 1 d . . . . .
H6 H 0.179334 0.089127 0.080055 0.076 Uiso 1 1 calc R U . . .
C7 C 0.19736(17) 0.14764(13) -0.35611(11) 0.0628(3) Uani 1 1 d . . . . .
H7 H 0.153818 0.044012 -0.383699 0.075 Uiso 1 1 calc R U . . .
C8 C 0.19119(16) 0.19593(13) -0.23899(11) 0.0591(3) Uani 1 1 d . . . . .
H8 H 0.143605 0.126096 -0.189327 0.071 Uiso 1 1 calc R U . . .
C9 C 0.25676(14) 0.35011(12) -0.19552(10) 0.0533(2) Uani 1 1 d D . . . .
C10 C 0.32959(17) 0.44889(13) -0.27255(12) 0.0619(3) Uani 1 1 d . . . . .
H10 H 0.378761 0.553408 -0.245844 0.074 Uiso 1 1 calc R U . . .
C11 C 0.32781(17) 0.38975(14) -0.38869(12) 0.0663(3) Uani 1 1 d . . . . .
H11 H 0.374977 0.456948 -0.440292 0.08 Uiso 1 1 calc R U . . .
C12 C 0.223(2) 0.3833(11) -0.0684(13) 0.0475(17) Uani 0.301(12) 1 d D U P A 1
H12 H 0.170336 0.300273 -0.031506 0.057 Uiso 0.301(12) 1 calc R U P A 1
C13 C 0.2604(10) 0.5118(10) -0.0097(8) 0.0498(13) Uani 0.301(12) 1 d D U P A 1
H13 H 0.319297 0.592465 -0.046909 0.06 Uiso 0.301(12) 1 calc R U P A 1
C14A C 0.227(2) 0.5586(14) 0.1103(11) 0.047(2) Uani 0.301(12) 1 d DG U P A 1
C15A C 0.148(2) 0.4496(11) 0.1788(12) 0.056(2) Uani 0.301(12) 1 d G U P A 1
H15A H 0.116116 0.348272 0.150776 0.067 Uiso 0.301(12) 1 calc R U P A 1
C16A C 0.117(2) 0.4919(14) 0.2890(12) 0.054(2) Uani 0.301(12) 1 d G U P A 1
H16A H 0.064359 0.418929 0.334749 0.065 Uiso 0.301(12) 1 calc R U P A 1
N2A N 0.165(2) 0.6433(15) 0.3308(11) 0.052(2) Uani 0.301(12) 1 d G U P A 1
C17A C 0.243(2) 0.7524(12) 0.2624(13) 0.055(2) Uani 0.301(12) 1 d G U P A 1
H17A H 0.275392 0.853681 0.290348 0.067 Uiso 0.301(12) 1 calc R U P A 1
C18A C 0.274(2) 0.7101(12) 0.1521(12) 0.054(2) Uani 0.301(12) 1 d G U P A 1
H18A H 0.327151 0.783027 0.106375 0.065 Uiso 0.301(12) 1 calc R U P A 1
C14B C 0.2145(9) 0.5257(7) 0.1226(5) 0.0514(10) Uani 0.699(12) 1 d D U P A 2
C15B C 0.1270(10) 0.4416(6) 0.2021(6) 0.0571(9) Uani 0.699(12) 1 d . U P A 2
H15B H 0.078653 0.336305 0.186284 0.068 Uiso 0.699(12) 1 calc R U P A 2
C16B C 0.1127(10) 0.5159(7) 0.3046(5) 0.0577(10) Uani 0.699(12) 1 d . U P A 2
H16B H 0.052215 0.456909 0.355943 0.069 Uiso 0.699(12) 1 calc R U P A 2
N2B N 0.1779(10) 0.6638(7) 0.3353(5) 0.0603(11) Uani 0.699(12) 1 d . U P A 2
C17B C 0.2610(10) 0.7416(6) 0.2593(6) 0.0627(11) Uani 0.699(12) 1 d . U P A 2
H17B H 0.310016 0.84683 0.27915 0.075 Uiso 0.699(12) 1 calc R U P A 2
C18B C 0.2816(9) 0.6816(7) 0.1537(6) 0.0567(9) Uani 0.699(12) 1 d . U P A 2
H18B H 0.339893 0.744518 0.103445 0.068 Uiso 0.699(12) 1 calc R U P A 2
C19 C 0.2525(10) 0.4156(8) -0.0807(6) 0.0610(12) Uani 0.699(12) 1 d D U P A 2
C20 C 0.2323(5) 0.4585(6) 0.0143(3) 0.0602(7) Uani 0.699(12) 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   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 1.3611(13) . ?
O1 H1 0.82 . ?
O2 C3 1.3554(14) . ?
O2 H2A 0.82 . ?
N1 C7 1.3305(16) . ?
N1 C11 1.3358(16) . ?
C1 C2 1.3833(15) . ?
C1 C6 1.3860(14) . ?
C2 C3 1.3900(15) . ?
C2 H2 0.93 . ?
C3 C4 1.3892(15) . ?
C4 C5 1.3736(19) . ?
C4 H4 0.93 . ?
C5 C6 1.3821(18) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.3720(15) . ?
C7 H7 0.93 . ?
C8 C9 1.3870(15) . ?
C8 H8 0.93 . ?
C9 C10 1.3863(16) . ?
C9 C19 1.406(6) . ?
C9 C12 1.548(11) . ?
C10 C11 1.3694(17) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 C13 1.263(12) . ?
C12 H12 0.93 . ?
C13 C14A 1.515(10) . ?
C13 H13 0.93 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.93 . ?
C16A N2A 1.39 . ?
C16A H16A 0.93 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.93 . ?
C18A H18A 0.93 . ?
C14B C18B 1.384(4) . ?
C14B C15B 1.386(4) . ?
C14B C20 1.409(5) . ?
C15B C16B 1.375(4) . ?
C15B H15B 0.93 . ?
C16B N2B 1.312(4) . ?
C16B H16B 0.93 . ?
N2B C17B 1.313(3) . ?
C17B C18B 1.364(3) . ?
C17B H17B 0.93 . ?
C18B H18B 0.93 . ?
C19 C20 1.190(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C7 N1 C11 116.90(10) . . ?
O1 C1 C2 121.95(9) . . ?
O1 C1 C6 118.19(10) . . ?
C2 C1 C6 119.86(10) . . ?
C1 C2 C3 120.39(9) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C4 117.96(10) . . ?
O2 C3 C2 122.19(9) . . ?
C4 C3 C2 119.85(11) . . ?
C5 C4 C3 118.95(11) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.88(10) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.06(11) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.44(11) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.23(10) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 117.71(10) . . ?
C10 C9 C19 116.7(3) . . ?
C8 C9 C19 125.6(3) . . ?
C10 C9 C12 129.7(4) . . ?
C8 C9 C12 112.4(4) . . ?
C11 C10 C9 118.79(10) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.90(11) . . ?
N1 C11 H11 118 . . ?
C10 C11 H11 118 . . ?
C13 C12 C9 126.5(11) . . ?
C13 C12 H12 116.7 . . ?
C9 C12 H12 116.7 . . ?
C12 C13 C14A 131.8(11) . . ?
C12 C13 H13 114.1 . . ?
C14A C13 H13 114.1 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13 119.8(7) . . ?
C18A C14A C13 120.2(7) . . ?
C16A C15A C14A 120 . . ?
C16A C15A H15A 120 . . ?
C14A C15A H15A 120 . . ?
C15A C16A N2A 120 . . ?
C15A C16A H16A 120 . . ?
N2A C16A H16A 120 . . ?
C16A N2A C17A 120 . . ?
C18A C17A N2A 120 . . ?
C18A C17A H17A 120 . . ?
N2A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C15B 116.2(2) . . ?
C18B C14B C20 121.0(4) . . ?
C15B C14B C20 122.8(3) . . ?
C16B C15B C14B 119.2(2) . . ?
C16B C15B H15B 120.4 . . ?
C14B C15B H15B 120.4 . . ?
N2B C16B C15B 124.9(2) . . ?
N2B C16B H16B 117.6 . . ?
C15B C16B H16B 117.6 . . ?
C16B N2B C17B 115.1(2) . . ?
N2B C17B C18B 125.8(3) . . ?
N2B C17B H17B 117.1 . . ?
C18B C17B H17B 117.1 . . ?
C17B C18B C14B 118.9(2) . . ?
C17B C18B H18B 120.5 . . ?
C14B C18B H18B 120.5 . . ?
C20 C19 C9 173.5(8) . . ?
C19 C20 C14B 173.4(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -179.40(9) . . . . ?
C6 C1 C2 C3 0.61(15) . . . . ?
C1 C2 C3 O2 178.38(9) . . . . ?
C1 C2 C3 C4 -1.38(16) . . . . ?
O2 C3 C4 C5 -178.54(11) . . . . ?
C2 C3 C4 C5 1.23(17) . . . . ?
C3 C4 C5 C6 -0.34(19) . . . . ?
C4 C5 C6 C1 -0.42(18) . . . . ?
O1 C1 C6 C5 -179.71(10) . . . . ?
C2 C1 C6 C5 0.28(16) . . . . ?
C11 N1 C7 C8 1.43(17) . . . . ?
N1 C7 C8 C9 -0.48(18) . . . . ?
C7 C8 C9 C10 -1.28(16) . . . . ?
C7 C8 C9 C19 177.4(4) . . . . ?
C7 C8 C9 C12 175.0(7) . . . . ?
C8 C9 C10 C11 2.01(16) . . . . ?
C19 C9 C10 C11 -176.7(3) . . . . ?
C12 C9 C10 C11 -173.5(8) . . . . ?
C7 N1 C11 C10 -0.62(18) . . . . ?
C9 C10 C11 N1 -1.10(18) . . . . ?
C10 C9 C12 C13 -1.1(19) . . . . ?
C8 C9 C12 C13 -176.8(12) . . . . ?
C9 C12 C13 C14A 176.8(11) . . . . ?
C12 C13 C14A C15A 3.0(17) . . . . ?
C12 C13 C14A C18A -177.0(13) . . . . ?
C18A C14A C15A C16A 0 . . . . ?
C13 C14A C15A C16A 179.9(12) . . . . ?
C14A C15A C16A N2A 0 . . . . ?
C15A C16A N2A C17A 0 . . . . ?
C16A N2A C17A C18A 0 . . . . ?
N2A C17A C18A C14A 0 . . . . ?
C15A C14A C18A C17A 0 . . . . ?
C13 C14A C18A C17A -179.9(12) . . . . ?
C18B C14B C15B C16B -0.1(3) . . . . ?
C20 C14B C15B C16B -178.9(6) . . . . ?
C14B C15B C16B N2B -0.6(3) . . . . ?
C15B C16B N2B C17B 0.4(3) . . . . ?
C16B N2B C17B C18B 0.7(4) . . . . ?
N2B C17B C18B C14B -1.5(4) . . . . ?
C15B C14B C18B C17B 1.1(3) . . . . ?
C20 C14B C18B C17B 179.9(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 2.7557(12) 172.7 1_556 yes
O2 H2A N2A^a 0.82 2 2.82(6) 172.4 2_666 yes
O2 H2A N2B^b 0.82 1.92 2.740(5) 176 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_BE25_BA75_210
_database_code_depnum_ccdc_archive 'CCDC 1995688'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

_audit_creation_date             2020-04-02T10:32:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C18 H14.59 N2 O2'
_chemical_formula_weight         290.9

#----------------------------------------------------------------------------#
#                   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                   8.17391(17)
_cell_length_b                   9.81420(15)
_cell_length_c                   10.94231(17)
_cell_angle_alpha                92.2144(13)
_cell_angle_beta                 108.1472(16)
_cell_angle_gamma                114.5712(17)
_cell_volume                     744.10(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    10658
_cell_measurement_theta_min      4.311
_cell_measurement_theta_max      77.224

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

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.082
_exptl_crystal_density_diffrn    1.298
_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
-2 6 -1 0.0431
5 -4 -4 0.0754
5 0 0 0.0393
1 -5 5 0.0478
0 -3 -5 0.0753
0 3 -6 0.0824
-5 0 0 0.0431
2 -6 2 0.0449
2 4 -1 0.0344
-3 -3 5 0.0681
5 -4 1 0.0424
3 -4 4 0.0384
3 0 4 0.0674
-3 -1 -4 0.0729
-1 1 7 0.0918
-1 -2 7 0.0812
3 -4 -5 0.0856
0 5 -4 0.0552

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

_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.9176
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.869
_shelx_estimated_absorpt_T_max   0.945

#----------------------------------------------------------------------------#
#                   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      -0.182013
_diffrn_orient_matrix_ub_12      -0.0495251
_diffrn_orient_matrix_ub_13      0.0354902
_diffrn_orient_matrix_ub_21      0.1272205
_diffrn_orient_matrix_ub_22      0.075972
_diffrn_orient_matrix_ub_23      0.1443638
_diffrn_orient_matrix_ub_31      -0.0070495
_diffrn_orient_matrix_ub_32      0.1507691
_diffrn_orient_matrix_ub_33      -0.0267924
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.038
_diffrn_reflns_number            14719
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_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         77.387
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.972
_reflns_Friedel_coverage         0
_reflns_number_total             3080
_reflns_number_gt                2809
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_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)+(0.0466P)²+0.0735P] 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       0.0035(7)
_refine_ls_number_reflns         3080
_refine_ls_number_parameters     265
_refine_ls_number_restraints     438
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0922
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.029

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

_refine_special_details          
;
 To help model the substitution of the bis(4-pyridyl)acetylene with 
 1,2-bis(4-pyridyl)ethylene, the atom sites N2 and  C14 < C18, were split into
 parts A and B. These sites along with C12, C13 (BPE), C19 and C20 (BPA) 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 BPA to BPE was 0.31
 to 0.69.
;

#----------------------------------------------------------------------------#
#                   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 0.16716(10) 0.14739(8) 0.30444(7) 0.04481(19) Uani 1 1 d . . . . .
H1 H 0.200279 0.172954 0.384871 0.067 Uiso 1 1 calc R U . . .
O2 O 0.81883(11) 0.21566(10) 0.43345(7) 0.0516(2) Uani 1 1 d . . . . .
H2A H 0.824479 0.252357 0.505132 0.077 Uiso 1 1 calc R U . . .
N1 N 0.26277(12) 0.24259(11) -0.43255(8) 0.0460(2) Uani 1 1 d . . . . .
C1 C 0.31760(14) 0.14715(10) 0.27614(9) 0.0372(2) Uani 1 1 d . . . . .
C2 C 0.49260(14) 0.18040(10) 0.37381(9) 0.0373(2) Uani 1 1 d . . . . .
H2 H 0.508822 0.203133 0.462298 0.045 Uiso 1 1 calc R U . . .
C3 C 0.64439(15) 0.18022(11) 0.34123(9) 0.0401(2) Uani 1 1 d . . . . .
C4 C 0.61921(17) 0.14325(12) 0.21028(10) 0.0472(2) Uani 1 1 d . . . . .
H4 H 0.719859 0.14081 0.187458 0.057 Uiso 1 1 calc R U . . .
C5 C 0.44405(18) 0.11025(13) 0.11460(10) 0.0506(3) Uani 1 1 d . . . . .
H5 H 0.426949 0.085786 0.026161 0.061 Uiso 1 1 calc R U . . .
C6 C 0.29263(16) 0.11215(11) 0.14524(10) 0.0459(2) Uani 1 1 d . . . . .
H6 H 0.174842 0.090116 0.078508 0.055 Uiso 1 1 calc R U . . .
C7 C 0.19762(15) 0.14692(12) -0.35639(10) 0.0447(2) Uani 1 1 d . . . . .
H7 H 0.154212 0.042053 -0.384517 0.054 Uiso 1 1 calc R U . . .
C8 C 0.19076(15) 0.19409(11) -0.23850(10) 0.0425(2) Uani 1 1 d . . . . .
H8 H 0.142243 0.122472 -0.188507 0.051 Uiso 1 1 calc R U . . .
C9 C 0.25650(13) 0.34894(11) -0.19455(9) 0.0389(2) Uani 1 1 d D . . . .
C10 C 0.32978(15) 0.44966(12) -0.27146(10) 0.0451(2) Uani 1 1 d . . . . .
H10 H 0.379378 0.555523 -0.244084 0.054 Uiso 1 1 calc R U . . .
C11 C 0.32840(15) 0.39154(13) -0.38846(11) 0.0480(3) Uani 1 1 d . . . . .
H11 H 0.37637 0.460538 -0.440438 0.058 Uiso 1 1 calc R U . . .
C12 C 0.2194(19) 0.3811(11) -0.0672(12) 0.0325(14) Uani 0.294(10) 1 d D U P A 1
H12 H 0.161531 0.298085 -0.029622 0.039 Uiso 0.294(10) 1 calc R U P A 1
C13 C 0.2648(8) 0.5173(9) -0.0110(6) 0.0337(11) Uani 0.294(10) 1 d D U P A 1
H13 H 0.326732 0.597669 -0.049564 0.04 Uiso 0.294(10) 1 calc R U P A 1
C14A C 0.2300(19) 0.5629(12) 0.1101(10) 0.0331(17) Uani 0.294(10) 1 d DG U P A
1
C15A C 0.1490(19) 0.4512(10) 0.1768(11) 0.0383(18) Uani 0.294(10) 1 d G U P A 1
H15A H 0.116806 0.348882 0.147442 0.046 Uiso 0.294(10) 1 calc R U P A 1
C16A C 0.1157(18) 0.4909(12) 0.2868(10) 0.0371(19) Uani 0.294(10) 1 d G U P A 1
H16A H 0.06098 0.415307 0.331949 0.045 Uiso 0.294(10) 1 calc R U P A 1
N2A N 0.163(2) 0.6422(13) 0.3302(10) 0.0344(18) Uani 0.294(10) 1 d G U P A 1
C17A C 0.244(2) 0.7539(11) 0.2635(12) 0.0377(19) Uani 0.294(10) 1 d G U P A 1
H17A H 0.276614 0.856248 0.292836 0.045 Uiso 0.294(10) 1 calc R U P A 1
C18A C 0.278(2) 0.7143(11) 0.1534(11) 0.0370(18) Uani 0.294(10) 1 d G U P A 1
H18A H 0.332441 0.789827 0.108328 0.044 Uiso 0.294(10) 1 calc R U P A 1
C14B C 0.2149(8) 0.5282(6) 0.1224(4) 0.0366(8) Uani 0.706(10) 1 d D U P A 2
C15B C 0.1262(8) 0.4418(5) 0.2018(5) 0.0406(7) Uani 0.706(10) 1 d . U P A 2
H15B H 0.077775 0.335005 0.185756 0.049 Uiso 0.706(10) 1 calc R U P A 2
C16B C 0.1107(8) 0.5154(6) 0.3046(5) 0.0410(9) Uani 0.706(10) 1 d . U P A 2
H16B H 0.049191 0.454868 0.356527 0.049 Uiso 0.706(10) 1 calc R U P A 2
N2B N 0.1759(9) 0.6649(6) 0.3354(5) 0.0433(9) Uani 0.706(10) 1 d . U P A 2
C17B C 0.2600(9) 0.7446(5) 0.2590(6) 0.0445(9) Uani 0.706(10) 1 d . U P A 2
H17B H 0.308835 0.851246 0.278815 0.053 Uiso 0.706(10) 1 calc R U P A 2
C18B C 0.2823(8) 0.6851(6) 0.1533(5) 0.0395(8) Uani 0.706(10) 1 d . U P A 2
H18B H 0.342113 0.749431 0.102613 0.047 Uiso 0.706(10) 1 calc R U P A 2
C19 C 0.2516(9) 0.4117(6) -0.0793(6) 0.0425(9) Uani 0.706(10) 1 d D U P A 2
C20 C 0.2347(4) 0.4627(5) 0.0146(3) 0.0429(6) Uani 0.706(10) 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   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(12) . ?
O1 H1 0.83 . ?
O2 C3 1.3552(12) . ?
O2 H2A 0.83 . ?
N1 C7 1.3344(14) . ?
N1 C11 1.3378(14) . ?
C1 C2 1.3883(14) . ?
C1 C6 1.3903(13) . ?
C2 C3 1.3942(14) . ?
C2 H2 0.94 . ?
C3 C4 1.3933(14) . ?
C4 C5 1.3803(16) . ?
C4 H4 0.94 . ?
C5 C6 1.3863(16) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3792(14) . ?
C7 H7 0.94 . ?
C8 C9 1.3903(14) . ?
C8 H8 0.94 . ?
C9 C10 1.3892(15) . ?
C9 C19 1.401(5) . ?
C9 C12 1.563(11) . ?
C10 C11 1.3762(15) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.297(12) . ?
C12 H12 0.94 . ?
C13 C14A 1.527(9) . ?
C13 H13 0.94 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.94 . ?
C16A N2A 1.39 . ?
C16A H16A 0.94 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.94 . ?
C18A H18A 0.94 . ?
C14B C18B 1.388(3) . ?
C14B C15B 1.392(3) . ?
C14B C20 1.407(4) . ?
C15B C16B 1.381(4) . ?
C15B H15B 0.94 . ?
C16B N2B 1.323(3) . ?
C16B H16B 0.94 . ?
N2B C17B 1.321(3) . ?
C17B C18B 1.371(3) . ?
C17B H17B 0.94 . ?
C18B H18B 0.94 . ?
C19 C20 1.196(6) . ?

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 . . ?
C7 N1 C11 117.05(9) . . ?
O1 C1 C2 121.81(8) . . ?
O1 C1 C6 118.21(9) . . ?
C2 C1 C6 119.98(9) . . ?
C1 C2 C3 120.29(9) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
O2 C3 C4 117.99(9) . . ?
O2 C3 C2 122.08(9) . . ?
C4 C3 C2 119.92(9) . . ?
C5 C4 C3 118.91(10) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.87(9) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.00(10) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.33(9) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.15(9) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 117.85(9) . . ?
C10 C9 C19 117.1(2) . . ?
C8 C9 C19 125.0(2) . . ?
C10 C9 C12 129.4(4) . . ?
C8 C9 C12 112.5(4) . . ?
C11 C10 C9 118.76(9) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.82(10) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13 C12 C9 123.0(9) . . ?
C13 C12 H12 118.5 . . ?
C9 C12 H12 118.5 . . ?
C12 C13 C14A 128.0(9) . . ?
C12 C13 H13 116 . . ?
C14A C13 H13 116 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13 119.3(5) . . ?
C18A C14A C13 120.7(5) . . ?
C14A C15A C16A 120 . . ?
C14A C15A H15A 120 . . ?
C16A C15A H15A 120 . . ?
N2A C16A C15A 120 . . ?
N2A C16A H16A 120 . . ?
C15A C16A H16A 120 . . ?
C16A N2A C17A 120 . . ?
C18A C17A N2A 120 . . ?
C18A C17A H17A 120 . . ?
N2A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C15B 116.65(19) . . ?
C18B C14B C20 120.5(3) . . ?
C15B C14B C20 122.8(3) . . ?
C16B C15B C14B 119.0(2) . . ?
C16B C15B H15B 120.5 . . ?
C14B C15B H15B 120.5 . . ?
N2B C16B C15B 124.8(2) . . ?
N2B C16B H16B 117.6 . . ?
C15B C16B H16B 117.6 . . ?
C17B N2B C16B 115.1(2) . . ?
N2B C17B C18B 125.7(2) . . ?
N2B C17B H17B 117.2 . . ?
C18B C17B H17B 117.2 . . ?
C17B C18B C14B 118.8(2) . . ?
C17B C18B H18B 120.6 . . ?
C14B C18B H18B 120.6 . . ?
C20 C19 C9 175.6(6) . . ?
C19 C20 C14B 177.4(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 -179.52(8) . . . . ?
C6 C1 C2 C3 0.57(14) . . . . ?
C1 C2 C3 O2 178.37(8) . . . . ?
C1 C2 C3 C4 -1.42(14) . . . . ?
O2 C3 C4 C5 -178.52(9) . . . . ?
C2 C3 C4 C5 1.29(15) . . . . ?
C3 C4 C5 C6 -0.33(16) . . . . ?
C4 C5 C6 C1 -0.51(16) . . . . ?
O1 C1 C6 C5 -179.52(9) . . . . ?
C2 C1 C6 C5 0.39(14) . . . . ?
C11 N1 C7 C8 1.73(15) . . . . ?
N1 C7 C8 C9 -0.76(16) . . . . ?
C7 C8 C9 C10 -1.13(14) . . . . ?
C7 C8 C9 C19 177.7(3) . . . . ?
C7 C8 C9 C12 174.2(6) . . . . ?
C8 C9 C10 C11 1.95(14) . . . . ?
C19 C9 C10 C11 -176.9(3) . . . . ?
C12 C9 C10 C11 -172.4(7) . . . . ?
C7 N1 C11 C10 -0.82(16) . . . . ?
C9 C10 C11 N1 -1.02(16) . . . . ?
C10 C9 C12 C13 -3.6(16) . . . . ?
C8 C9 C12 C13 -178.3(9) . . . . ?
C9 C12 C13 C14A 177.7(9) . . . . ?
C12 C13 C14A C15A 3.6(14) . . . . ?
C12 C13 C14A C18A -176.1(10) . . . . ?
C18A C14A C15A C16A 0 . . . . ?
C13 C14A C15A C16A -179.7(10) . . . . ?
C14A C15A C16A N2A 0 . . . . ?
C15A C16A N2A C17A 0 . . . . ?
C16A N2A C17A C18A 0 . . . . ?
N2A C17A C18A C14A 0 . . . . ?
C15A C14A C18A C17A 0 . . . . ?
C13 C14A C18A C17A 179.7(10) . . . . ?
C18B C14B C15B C16B 0.0(3) . . . . ?
C20 C14B C15B C16B -179.1(5) . . . . ?
C14B C15B C16B N2B -0.6(3) . . . . ?
C15B C16B N2B C17B 0.4(3) . . . . ?
C16B N2B C17B C18B 0.5(3) . . . . ?
N2B C17B C18B C14B -1.1(3) . . . . ?
C15B C14B C18B C17B 0.7(3) . . . . ?
C20 C14B C18B C17B 179.9(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 1.92 2.7478(11) 174.6 1_556 yes
O2 H2A N2A^a 0.83 2 2.82(5) 174.4 2_666 yes
O2 H2A N2B^b 0.83 1.9 2.726(4) 177 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_BE50_BA50_190
_database_code_depnum_ccdc_archive 'CCDC 1995693'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT155_BE50_BA50_190       
;
PROBLEM: The Triclinic Unitcell is NOT Reduced ..........     Please Do !  
RESPONSE: The unit cell was not reduced to maintain continuity throughout 
          the structures and temperatures.
;
_vrf_PLAT911_BE50_BA50_190       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          4 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2020-04-01T17:45:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C18 H15.03 N2 O2'
_chemical_formula_weight         291.34

#----------------------------------------------------------------------------#
#                   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                   8.12328(14)
_cell_length_b                   9.8351(2)
_cell_length_c                   10.91847(14)
_cell_angle_alpha                92.3839(18)
_cell_angle_beta                 107.8562(13)
_cell_angle_gamma                114.4977(15)
_cell_volume                     741.07(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    18862
_cell_measurement_theta_min      4.315
_cell_measurement_theta_max      76.705

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

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.088
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             306
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 2 0.1024
2 0 -6 0.081
4 5 0 0.0438
-5 -4 -3 0.0658
-1 4 4 0.0337
-4 -5 0 0.0468
2 6 4 0.0464
5 5 4 0.0804
5 4 -1 0.0444
3 2 -4 0.0582
1 6 -1 0.0561
-1 -6 1 0.0835
-5 -2 0 0.0435
2 -4 2 0.0954
-3 2 1 0.0427
0 6 2 0.0367
2 6 3 0.0426
-2 -6 -3 0.0582
1 2 7 0.0957
4 6 1 0.0435
1 -5 0 0.0733
2 -2 -5 0.054
-4 -6 -4 0.0654
1 -5 -4 0.0508

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

_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.81639
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.887
_shelx_estimated_absorpt_T_max   0.955

#----------------------------------------------------------------------------#
#                   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      -0.0033213
_diffrn_orient_matrix_ub_12      -0.0566512
_diffrn_orient_matrix_ub_13      0.1479079
_diffrn_orient_matrix_ub_21      -0.1506942
_diffrn_orient_matrix_ub_22      0.1531359
_diffrn_orient_matrix_ub_23      0.0272409
_diffrn_orient_matrix_ub_31      -0.1504746
_diffrn_orient_matrix_ub_32      -0.0643381
_diffrn_orient_matrix_ub_33      0.0149157
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_number            28099
_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         77.324
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_reflns_Friedel_coverage         0
_reflns_number_total             3073
_reflns_number_gt                2863
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_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)+(0.0444P)²+0.0938P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_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(7)
_refine_ls_number_reflns         3073
_refine_ls_number_parameters     267
_refine_ls_number_restraints     460
_refine_ls_R_factor_all          0.034
_refine_ls_R_factor_gt           0.032
_refine_ls_wR_factor_ref         0.0876
_refine_ls_wR_factor_gt          0.086
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.029

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

_refine_special_details          
;
 To help model the substitution of the bis(4-pyridyl)acetylene with 
 1,2-bis(4-pyridyl)ethylene, the atom sites N2 and  C14 < C18, were split into
 parts A and B. These sites along with C12, C13 (BPE), C19 and C20 (BPA) 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 BPE to BPA was 0.51
 to 0.49.
;

#----------------------------------------------------------------------------#
#                   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 0.16658(9) 0.15097(8) 0.30486(7) 0.03979(18) Uani 1 1 d . . . . .
H1 H 0.2057(8) 0.1817(15) 0.3989(14) 0.06 Uiso 1 1 calc R U . . .
O2 O 0.82157(10) 0.22084(9) 0.43309(7) 0.04583(19) Uani 1 1 d . . . . .
H2A H 0.8271(7) 0.2636(16) 0.5184(14) 0.069 Uiso 1 1 calc R U . . .
N1 N 0.26273(12) 0.24430(10) -0.43203(8) 0.0412(2) Uani 1 1 d . . . . .
C1 C 0.31725(13) 0.14956(9) 0.27605(8) 0.0330(2) Uani 1 1 d . . . . .
C2 C 0.49378(13) 0.18479(9) 0.37361(8) 0.0332(2) Uani 1 1 d . . . . .
H2 H 0.51065 0.209702 0.463047 0.04 Uiso 1 1 calc R U . . .
C3 C 0.64585(14) 0.18372(10) 0.34089(9) 0.0356(2) Uani 1 1 d . . . . .
C4 C 0.62020(15) 0.14405(11) 0.20978(9) 0.0414(2) Uani 1 1 d . . . . .
H4 H 0.722582 0.141423 0.186624 0.05 Uiso 1 1 calc R U . . .
C5 C 0.44318(16) 0.10864(11) 0.11414(9) 0.0444(2) Uani 1 1 d . . . . .
H5 H 0.425367 0.081942 0.024781 0.053 Uiso 1 1 calc R U . . .
C6 C 0.29114(15) 0.11104(11) 0.14507(9) 0.0403(2) Uani 1 1 d . . . . .
H6 H 0.170847 0.08674 0.077853 0.048 Uiso 1 1 calc R U . . .
C7 C 0.19720(14) 0.14668(11) -0.35703(9) 0.0399(2) Uani 1 1 d . . . . .
H7 H 0.154484 0.041401 -0.386674 0.048 Uiso 1 1 calc R U . . .
C8 C 0.18857(14) 0.19132(11) -0.23866(9) 0.0378(2) Uani 1 1 d . . . . .
H8 H 0.13963 0.117626 -0.189051 0.045 Uiso 1 1 calc R U . . .
C9 C 0.25193(13) 0.34483(11) -0.19242(9) 0.0352(2) Uani 1 1 d D U . . .
C10 C 0.32590(14) 0.44748(11) -0.26821(10) 0.0407(2) Uani 1 1 d . . . . .
H10 H 0.375131 0.553846 -0.239197 0.049 Uiso 1 1 calc R U . . .
C11 C 0.32657(15) 0.39233(12) -0.38593(10) 0.0429(2) Uani 1 1 d . . . . .
H11 H 0.375157 0.463439 -0.437526 0.051 Uiso 1 1 calc R U . . .
C12 C 0.2189(10) 0.3794(6) -0.0663(6) 0.0289(8) Uani 0.513(10) 1 d D U P A 1
H12 H 0.162026 0.297113 -0.026265 0.035 Uiso 0.513(10) 1 calc R U P A 1
C13 C 0.2664(4) 0.5190(5) -0.0108(3) 0.0288(6) Uani 0.513(10) 1 d D U P A 1
H13 H 0.327583 0.599737 -0.050843 0.035 Uiso 0.513(10) 1 calc R U P A 1
C14A C 0.2319(11) 0.5619(7) 0.1106(6) 0.0281(10) Uani 0.513(10) 1 d G U P A 1
C15A C 0.1476(12) 0.4533(6) 0.1785(7) 0.0332(11) Uani 0.513(10) 1 d G U P A 1
H15A H 0.110972 0.349016 0.149508 0.04 Uiso 0.513(10) 1 calc R U P A 1
C16A C 0.1169(12) 0.4971(7) 0.2890(7) 0.0344(12) Uani 0.513(10) 1 d G U P A 1
H16A H 0.059292 0.422874 0.335387 0.041 Uiso 0.513(10) 1 calc R U P A 1
N2A N 0.1705(12) 0.6497(8) 0.3314(6) 0.0320(13) Uani 0.513(10) 1 d G U P A 1
C17A C 0.2548(11) 0.7584(6) 0.2635(6) 0.0317(10) Uani 0.513(10) 1 d G U P A 1
H17A H 0.291445 0.862624 0.292516 0.038 Uiso 0.513(10) 1 calc R U P A 1
C18A C 0.2855(11) 0.7145(6) 0.1531(6) 0.0305(10) Uani 0.513(10) 1 d G U P A 1
H18A H 0.343127 0.788769 0.106636 0.037 Uiso 0.513(10) 1 calc R U P A 1
C14B C 0.2162(13) 0.5280(9) 0.1214(7) 0.0358(13) Uani 0.487(10) 1 d . U P A 2
C15B C 0.1284(14) 0.4436(8) 0.2023(8) 0.0405(12) Uani 0.487(10) 1 d . U P A 2
H15B H 0.079037 0.335956 0.187025 0.049 Uiso 0.487(10) 1 calc R U P A 2
C16B C 0.1142(14) 0.5185(9) 0.3045(8) 0.0395(12) Uani 0.487(10) 1 d . U P A 2
H16B H 0.052157 0.456757 0.356934 0.047 Uiso 0.487(10) 1 calc R U P A 2
N2B N 0.1753(14) 0.6630(10) 0.3375(8) 0.0438(16) Uani 0.487(10) 1 d . U P A 2
C17B C 0.2557(14) 0.7380(9) 0.2611(9) 0.0421(13) Uani 0.487(10) 1 d . U P A 2
H17B H 0.304059 0.845412 0.281329 0.051 Uiso 0.487(10) 1 calc R U P A 2
C18B C 0.2807(12) 0.6832(8) 0.1545(7) 0.0362(11) Uani 0.487(10) 1 d . U P A 2
H18B H 0.341143 0.750262 0.104381 0.043 Uiso 0.487(10) 1 calc R U P A 2
C19 C 0.2507(12) 0.4105(9) -0.0794(8) 0.0405(12) Uani 0.487(10) 1 d D U P A 2
C20 C 0.2361(6) 0.4643(7) 0.0145(4) 0.0421(9) Uani 0.487(10) 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   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(11) . ?
O1 H1 0.970(14) . ?
O2 C3 1.3565(12) . ?
O2 H2A 0.986(15) . ?
N1 C7 1.3358(13) . ?
N1 C11 1.3397(13) . ?
C1 C2 1.3898(13) . ?
C1 C6 1.3914(12) . ?
C2 C3 1.3910(13) . ?
C2 H2 0.95 . ?
C3 C4 1.3958(13) . ?
C4 C5 1.3831(15) . ?
C4 H4 0.95 . ?
C5 C6 1.3854(15) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.3791(13) . ?
C7 H7 0.95 . ?
C8 C9 1.3900(13) . ?
C8 H8 0.95 . ?
C9 C19 1.374(8) . ?
C9 C10 1.3916(14) . ?
C9 C12 1.532(6) . ?
C10 C11 1.3765(14) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
C12 C13 1.323(7) . ?
C12 H12 0.95 . ?
C13 C14A 1.514(5) . ?
C13 H13 0.95 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.95 . ?
C16A N2A 1.39 . ?
C16A H16A 0.95 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.95 . ?
C18A H18A 0.95 . ?
C14B C18B 1.381(5) . ?
C14B C20 1.386(6) . ?
C14B C15B 1.391(6) . ?
C15B C16B 1.372(5) . ?
C15B H15B 0.95 . ?
C16B N2B 1.287(5) . ?
C16B H16B 0.95 . ?
N2B C17B 1.286(5) . ?
C17B C18B 1.367(4) . ?
C17B H17B 0.95 . ?
C18B H18B 0.95 . ?
C19 C20 1.194(8) . ?

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 . . ?
C7 N1 C11 116.96(8) . . ?
O1 C1 C2 121.65(8) . . ?
O1 C1 C6 118.32(8) . . ?
C2 C1 C6 120.03(9) . . ?
C1 C2 C3 120.29(8) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
O2 C3 C2 122.00(8) . . ?
O2 C3 C4 118.02(8) . . ?
C2 C3 C4 119.97(9) . . ?
C5 C4 C3 118.87(9) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.82(9) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.01(9) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.18(9) . . ?
N1 C7 H7 118.4 . . ?
C8 C7 H7 118.4 . . ?
C7 C8 C9 119.57(9) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C19 C9 C8 128.1(3) . . ?
C19 C9 C10 114.5(3) . . ?
C8 C9 C10 117.47(9) . . ?
C8 C9 C12 114.9(2) . . ?
C10 C9 C12 127.5(2) . . ?
C11 C10 C9 118.90(9) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.87(9) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13 C12 C9 122.7(5) . . ?
C13 C12 H12 118.6 . . ?
C9 C12 H12 118.6 . . ?
C12 C13 C14A 125.9(5) . . ?
C12 C13 H13 117 . . ?
C14A C13 H13 117 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13 121.8(3) . . ?
C18A C14A C13 118.2(3) . . ?
C14A C15A C16A 120 . . ?
C14A C15A H15A 120 . . ?
C16A C15A H15A 120 . . ?
N2A C16A C15A 120 . . ?
N2A C16A H16A 120 . . ?
C15A C16A H16A 120 . . ?
C16A N2A C17A 120 . . ?
C18A C17A N2A 120 . . ?
C18A C17A H17A 120 . . ?
N2A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C20 121.7(5) . . ?
C18B C14B C15B 114.5(3) . . ?
C20 C14B C15B 123.8(4) . . ?
C16B C15B C14B 118.9(3) . . ?
C16B C15B H15B 120.6 . . ?
C14B C15B H15B 120.6 . . ?
N2B C16B C15B 127.4(4) . . ?
N2B C16B H16B 116.3 . . ?
C15B C16B H16B 116.3 . . ?
C17B N2B C16B 112.3(4) . . ?
N2B C17B C18B 128.4(4) . . ?
N2B C17B H17B 115.8 . . ?
C18B C17B H17B 115.8 . . ?
C17B C18B C14B 118.5(3) . . ?
C17B C18B H18B 120.7 . . ?
C14B C18B H18B 120.7 . . ?
C20 C19 C9 175.4(8) . . ?
C19 C20 C14B 178.6(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 0.97 1.77 2.7414(10) 175.1 1_556 yes
O2 H2A N2A^a 0.99 1.81 2.79(3) 175.8 2_666 yes
O2 H2A N2B^b 0.99 1.71 2.698(6) 177 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_BE25_BA75_270
_database_code_depnum_ccdc_archive 'CCDC 1995691'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

_audit_creation_date             2020-04-02T10:38:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C18 H14.61 N2 O2'
_chemical_formula_weight         290.93

#----------------------------------------------------------------------------#
#                   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                   8.21931(13)
_cell_length_b                   9.84133(13)
_cell_length_c                   10.95472(14)
_cell_angle_alpha                92.4662(11)
_cell_angle_beta                 108.0057(13)
_cell_angle_gamma                114.4642(14)
_cell_volume                     751.94(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    9729
_cell_measurement_theta_min      4.312
_cell_measurement_theta_max      76.764

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

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.082
_exptl_crystal_density_diffrn    1.285
_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
-2 6 -1 0.0431
-5 0 0 0.0431
1 -5 5 0.0478
5 0 0 0.0393
-1 -2 7 0.0812
2 -6 2 0.0449
0 3 -6 0.0824
0 5 -4 0.0552
5 -4 -4 0.0754
2 4 -1 0.0344
-3 -3 5 0.0681
5 -4 1 0.0424
3 0 4 0.0674
3 -4 4 0.0384
-3 -1 -4 0.0729
-1 1 7 0.0918
0 -3 -5 0.0753
3 -4 -5 0.0856

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

_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.90133
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.87
_shelx_estimated_absorpt_T_max   0.946

#----------------------------------------------------------------------------#
#                   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      -0.1806034
_diffrn_orient_matrix_ub_12      -0.0487002
_diffrn_orient_matrix_ub_13      0.0357711
_diffrn_orient_matrix_ub_21      0.126618
_diffrn_orient_matrix_ub_22      0.0762334
_diffrn_orient_matrix_ub_23      0.1440904
_diffrn_orient_matrix_ub_31      -0.006865
_diffrn_orient_matrix_ub_32      0.1503187
_diffrn_orient_matrix_ub_33      -0.0266992
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_number            14792
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.329
_diffrn_reflns_theta_max         77.34
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.969
_reflns_Friedel_coverage         0
_reflns_number_total             3110
_reflns_number_gt                2735
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_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)+(0.0519P)²+0.0536P] 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(8)
_refine_ls_number_reflns         3110
_refine_ls_number_parameters     265
_refine_ls_number_restraints     438
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.02
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.027

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

_refine_special_details          
;
 To help model the substitution of the bis(4-pyridyl)acetylene with 
 1,2-bis(4-pyridyl)ethylene, the atom sites N2 and  C14 < C18, were split into
 parts A and B. These sites along with C12, C13 (BPE), C19 and C20 (BPA) 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 BPA to BPE was 0.31
 to 0.69.
;

#----------------------------------------------------------------------------#
#                   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 0.16877(11) 0.14590(9) 0.30453(7) 0.0586(2) Uani 1 1 d . . . . .
H1 H 0.200784 0.170181 0.38399 0.088 Uiso 1 1 calc R U . . .
O2 O 0.81662(12) 0.21565(11) 0.43249(8) 0.0674(2) Uani 1 1 d . . . . .
H2A H 0.821508 0.250611 0.50357 0.101 Uiso 1 1 calc R U . . .
N1 N 0.26244(13) 0.24159(11) -0.43237(9) 0.0590(2) Uani 1 1 d . . . . .
C1 C 0.31854(15) 0.14617(10) 0.27609(9) 0.0477(2) Uani 1 1 d . . . . .
C2 C 0.49240(15) 0.17962(11) 0.37325(9) 0.0480(2) Uani 1 1 d . . . . .
H2 H 0.508239 0.201947 0.460745 0.058 Uiso 1 1 calc R U . . .
C3 C 0.64323(16) 0.17999(11) 0.34065(10) 0.0516(2) Uani 1 1 d . . . . .
C4 C 0.61840(18) 0.14347(13) 0.21000(11) 0.0607(3) Uani 1 1 d . . . . .
H4 H 0.71753 0.141456 0.187244 0.073 Uiso 1 1 calc R U . . .
C5 C 0.4448(2) 0.11034(14) 0.11493(11) 0.0647(3) Uani 1 1 d . . . . .
H5 H 0.428272 0.086434 0.027488 0.078 Uiso 1 1 calc R U . . .
C6 C 0.29430(18) 0.11157(12) 0.14558(10) 0.0590(3) Uani 1 1 d . . . . .
H6 H 0.178496 0.089511 0.079679 0.071 Uiso 1 1 calc R U . . .
C7 C 0.19737(16) 0.14745(13) -0.35624(11) 0.0579(3) Uani 1 1 d . . . . .
H7 H 0.15399 0.043791 -0.38388 0.069 Uiso 1 1 calc R U . . .
C8 C 0.19099(16) 0.19552(12) -0.23894(11) 0.0548(3) Uani 1 1 d . . . . .
H8 H 0.143164 0.125402 -0.189386 0.066 Uiso 1 1 calc R U . . .
C9 C 0.25665(14) 0.34976(12) -0.19525(10) 0.0493(2) Uani 1 1 d D . . . .
C10 C 0.32952(16) 0.44898(13) -0.27232(11) 0.0576(3) Uani 1 1 d . . . . .
H10 H 0.378606 0.553556 -0.24555 0.069 Uiso 1 1 calc R U . . .
C11 C 0.32789(17) 0.39007(14) -0.38876(12) 0.0615(3) Uani 1 1 d . . . . .
H11 H 0.375141 0.457516 -0.440327 0.074 Uiso 1 1 calc R U . . .
C12 C 0.220(2) 0.3831(11) -0.0691(13) 0.0436(16) Uani 0.306(12) 1 d D U P A 1
H12 H 0.163116 0.299875 -0.033668 0.052 Uiso 0.306(12) 1 calc R U P A 1
C13 C 0.2614(9) 0.5126(10) -0.0099(8) 0.0463(13) Uani 0.306(12) 1 d D U P A 1
H13 H 0.324828 0.59366 -0.04518 0.056 Uiso 0.306(12) 1 calc R U P A 1
C14A C 0.2242(19) 0.5581(13) 0.1096(10) 0.0431(19) Uani 0.306(12) 1 d DG U P A
1
C15A C 0.146(2) 0.4489(10) 0.1783(12) 0.053(2) Uani 0.306(12) 1 d G U P A 1
H15A H 0.113817 0.347559 0.150435 0.063 Uiso 0.306(12) 1 calc R U P A 1
C16A C 0.115(2) 0.4913(13) 0.2887(12) 0.050(2) Uani 0.306(12) 1 d G U P A 1
H16A H 0.062518 0.418313 0.334629 0.061 Uiso 0.306(12) 1 calc R U P A 1
N2A N 0.163(2) 0.6429(15) 0.3303(11) 0.048(2) Uani 0.306(12) 1 d G U P A 1
C17A C 0.241(2) 0.7520(11) 0.2616(11) 0.0490(19) Uani 0.306(12) 1 d G U P A 1
H17A H 0.273199 0.853388 0.289477 0.059 Uiso 0.306(12) 1 calc R U P A 1
C18A C 0.2720(18) 0.7096(11) 0.1513(10) 0.0482(19) Uani 0.306(12) 1 d G U P A 1
H18A H 0.324499 0.782636 0.105282 0.058 Uiso 0.306(12) 1 calc R U P A 1
C14B C 0.2158(9) 0.5265(7) 0.1229(5) 0.0479(9) Uani 0.694(12) 1 d D U P A 2
C15B C 0.1276(10) 0.4420(5) 0.2022(6) 0.0529(9) Uani 0.694(12) 1 d . U P A 2
H15B H 0.079061 0.336598 0.18639 0.064 Uiso 0.694(12) 1 calc R U P A 2
C16B C 0.1128(10) 0.5163(7) 0.3045(5) 0.0534(10) Uani 0.694(12) 1 d . U P A 2
H16B H 0.051818 0.457036 0.35572 0.064 Uiso 0.694(12) 1 calc R U P A 2
N2B N 0.1782(10) 0.6645(7) 0.3355(5) 0.0555(11) Uani 0.694(12) 1 d . U P A 2
C17B C 0.2620(10) 0.7425(6) 0.2596(6) 0.0580(11) Uani 0.694(12) 1 d . U P A 2
H17B H 0.311182 0.847857 0.279505 0.07 Uiso 0.694(12) 1 calc R U P A 2
C18B C 0.2833(8) 0.6827(6) 0.1541(5) 0.0520(9) Uani 0.694(12) 1 d . U P A 2
H18B H 0.342223 0.745789 0.104001 0.062 Uiso 0.694(12) 1 calc R U P A 2
C19 C 0.2535(10) 0.4148(7) -0.0799(6) 0.0557(11) Uani 0.694(12) 1 d D U P A 2
C20 C 0.2327(5) 0.4595(6) 0.0144(3) 0.0552(7) Uani 0.694(12) 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   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 1.3590(13) . ?
O1 H1 0.82 . ?
O2 C3 1.3548(13) . ?
O2 H2A 0.82 . ?
N1 C7 1.3310(15) . ?
N1 C11 1.3353(15) . ?
C1 C2 1.3868(15) . ?
C1 C6 1.3876(14) . ?
C2 C3 1.3909(15) . ?
C2 H2 0.93 . ?
C3 C4 1.3906(15) . ?
C4 C5 1.3759(18) . ?
C4 H4 0.93 . ?
C5 C6 1.3830(18) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.3739(15) . ?
C7 H7 0.93 . ?
C8 C9 1.3870(15) . ?
C8 H8 0.93 . ?
C9 C10 1.3872(16) . ?
C9 C19 1.404(6) . ?
C9 C12 1.549(12) . ?
C10 C11 1.3721(16) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 C13 1.264(12) . ?
C12 H12 0.93 . ?
C13 C14A 1.522(10) . ?
C13 H13 0.93 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.93 . ?
C16A N2A 1.39 . ?
C16A H16A 0.93 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.93 . ?
C18A H18A 0.93 . ?
C14B C18B 1.385(4) . ?
C14B C15B 1.387(4) . ?
C14B C20 1.405(5) . ?
C15B C16B 1.376(4) . ?
C15B H15B 0.93 . ?
C16B N2B 1.314(4) . ?
C16B H16B 0.93 . ?
N2B C17B 1.314(3) . ?
C17B C18B 1.366(3) . ?
C17B H17B 0.93 . ?
C18B H18B 0.93 . ?
C19 C20 1.193(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C7 N1 C11 116.98(9) . . ?
O1 C1 C2 121.90(9) . . ?
O1 C1 C6 118.28(10) . . ?
C2 C1 C6 119.82(10) . . ?
C1 C2 C3 120.41(9) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C4 117.98(10) . . ?
O2 C3 C2 122.18(9) . . ?
C4 C3 C2 119.84(10) . . ?
C5 C4 C3 118.95(11) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.93(10) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.04(11) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.38(10) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.27(10) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C10 117.68(10) . . ?
C8 C9 C19 125.6(3) . . ?
C10 C9 C19 116.7(3) . . ?
C8 C9 C12 112.7(4) . . ?
C10 C9 C12 129.4(4) . . ?
C11 C10 C9 118.81(10) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.84(10) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13 C12 C9 126.2(10) . . ?
C13 C12 H12 116.9 . . ?
C9 C12 H12 116.9 . . ?
C12 C13 C14A 130.8(11) . . ?
C12 C13 H13 114.6 . . ?
C14A C13 H13 114.6 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13 120.2(6) . . ?
C18A C14A C13 119.8(6) . . ?
C14A C15A C16A 120 . . ?
C14A C15A H15A 120 . . ?
C16A C15A H15A 120 . . ?
N2A C16A C15A 120 . . ?
N2A C16A H16A 120 . . ?
C15A C16A H16A 120 . . ?
C17A N2A C16A 120 . . ?
N2A C17A C18A 120 . . ?
N2A C17A H17A 120 . . ?
C18A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C15B 116.2(2) . . ?
C18B C14B C20 121.0(4) . . ?
C15B C14B C20 122.8(3) . . ?
C16B C15B C14B 119.2(2) . . ?
C16B C15B H15B 120.4 . . ?
C14B C15B H15B 120.4 . . ?
N2B C16B C15B 125.0(2) . . ?
N2B C16B H16B 117.5 . . ?
C15B C16B H16B 117.5 . . ?
C17B N2B C16B 115.0(2) . . ?
N2B C17B C18B 125.8(3) . . ?
N2B C17B H17B 117.1 . . ?
C18B C17B H17B 117.1 . . ?
C17B C18B C14B 118.9(2) . . ?
C17B C18B H18B 120.6 . . ?
C14B C18B H18B 120.6 . . ?
C20 C19 C9 173.6(7) . . ?
C19 C20 C14B 174.4(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -179.52(9) . . . . ?
C6 C1 C2 C3 0.56(15) . . . . ?
C1 C2 C3 O2 178.38(9) . . . . ?
C1 C2 C3 C4 -1.36(15) . . . . ?
O2 C3 C4 C5 -178.50(10) . . . . ?
C2 C3 C4 C5 1.25(16) . . . . ?
C3 C4 C5 C6 -0.34(18) . . . . ?
C4 C5 C6 C1 -0.46(18) . . . . ?
O1 C1 C6 C5 -179.58(10) . . . . ?
C2 C1 C6 C5 0.35(15) . . . . ?
C11 N1 C7 C8 1.51(17) . . . . ?
N1 C7 C8 C9 -0.61(17) . . . . ?
C7 C8 C9 C10 -1.15(16) . . . . ?
C7 C8 C9 C19 177.9(4) . . . . ?
C7 C8 C9 C12 174.1(6) . . . . ?
C8 C9 C10 C11 1.91(16) . . . . ?
C19 C9 C10 C11 -177.2(4) . . . . ?
C12 C9 C10 C11 -172.4(8) . . . . ?
C7 N1 C11 C10 -0.67(17) . . . . ?
C9 C10 C11 N1 -1.05(18) . . . . ?
C8 C9 C12 C13 -178.3(11) . . . . ?
C10 C9 C12 C13 -3.7(18) . . . . ?
C9 C12 C13 C14A 176.6(10) . . . . ?
C12 C13 C14A C15A 5.7(15) . . . . ?
C12 C13 C14A C18A -175.4(12) . . . . ?
C18A C14A C15A C16A 0 . . . . ?
C13 C14A C15A C16A 178.9(11) . . . . ?
C14A C15A C16A N2A 0 . . . . ?
C15A C16A N2A C17A 0 . . . . ?
C16A N2A C17A C18A 0 . . . . ?
N2A C17A C18A C14A 0 . . . . ?
C15A C14A C18A C17A 0 . . . . ?
C13 C14A C18A C17A -178.9(11) . . . . ?
C18B C14B C15B C16B -0.1(3) . . . . ?
C20 C14B C15B C16B -178.4(5) . . . . ?
C14B C15B C16B N2B -0.7(3) . . . . ?
C15B C16B N2B C17B 0.4(3) . . . . ?
C16B N2B C17B C18B 0.7(4) . . . . ?
N2B C17B C18B C14B -1.4(4) . . . . ?
C15B C14B C18B C17B 1.0(3) . . . . ?
C20 C14B C18B C17B 179.3(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 2.7533(12) 173.7 1_556 yes
O2 H2A N2A^a 0.82 2 2.82(6) 173.7 2_666 yes
O2 H2A N2B^b 0.82 1.92 2.737(4) 176.7 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_BE50_BA50_210
_database_code_depnum_ccdc_archive 'CCDC 1995694'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT155_BE50_BA50_210       
;
PROBLEM: The Triclinic Unitcell is NOT Reduced ..........     Please Do !  
RESPONSE: The unit cell was not reduced to maintain continuity throughout 
          the structures and temperatures.
;
_vrf_PLAT911_BE50_BA50_210       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          4 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2020-04-01T17:45:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C18 H15.01 N2 O2'
_chemical_formula_weight         291.33

#----------------------------------------------------------------------------#
#                   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                   8.13837(14)
_cell_length_b                   9.8450(2)
_cell_length_c                   10.92312(12)
_cell_angle_alpha                92.4784(16)
_cell_angle_beta                 107.8241(12)
_cell_angle_gamma                114.4657(15)
_cell_volume                     743.63(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    18331
_cell_measurement_theta_min      4.322
_cell_measurement_theta_max      76.206

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

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.088
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             306
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 2 0.1024
1 -5 -4 0.0508
-4 -6 -4 0.0654
2 6 4 0.0464
4 6 1 0.0435
1 2 7 0.0957
1 6 -1 0.0561
2 -2 -5 0.054
1 -5 0 0.0733
0 6 2 0.0367
-4 2 1 0.0427
-1 -6 1 0.0835
3 2 -4 0.0582
5 4 -1 0.0444
5 5 4 0.0804
-5 -4 -3 0.0658
-5 -2 0 0.0435
2 -4 2 0.0954
-4 -5 0 0.0468
-1 4 4 0.0337
2 6 3 0.0426
-2 -6 -3 0.0582
4 5 0 0.0438
2 0 -6 0.081

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

_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.83548
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.888
_shelx_estimated_absorpt_T_max   0.956

#----------------------------------------------------------------------------#
#                   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      -0.0032376
_diffrn_orient_matrix_ub_12      -0.0565981
_diffrn_orient_matrix_ub_13      0.1478999
_diffrn_orient_matrix_ub_21      -0.1510082
_diffrn_orient_matrix_ub_22      0.1527942
_diffrn_orient_matrix_ub_23      0.0270556
_diffrn_orient_matrix_ub_31      -0.1496497
_diffrn_orient_matrix_ub_32      -0.0647266
_diffrn_orient_matrix_ub_33      0.0148352
_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     0.0454
_diffrn_reflns_number            28285
_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         4.336
_diffrn_reflns_theta_max         77.217
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_reflns_Friedel_coverage         0
_reflns_number_total             3085
_reflns_number_gt                2850
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_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)+(0.0462P)²+0.0924P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_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(7)
_refine_ls_number_reflns         3085
_refine_ls_number_parameters     267
_refine_ls_number_restraints     460
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      0.99
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.029

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

_refine_special_details          
;
 To help model the substitution of the bis(4-pyridyl)acetylene with 
 1,2-bis(4-pyridyl)ethylene, the atom sites N2 and  C14 < C18, were split into
 parts A and B. These sites along with C12, C13 (BPE), C19 and C20 (BPA) 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 BPE to BPA was 0.51
 to 0.49.
;

#----------------------------------------------------------------------------#
#                   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 0.16705(10) 0.15041(8) 0.30484(7) 0.04387(19) Uani 1 1 d . . . . .
H1 H 0.2063(8) 0.1812(15) 0.3996(14) 0.066 Uiso 1 1 calc R U . . .
O2 O 0.82074(11) 0.22074(9) 0.43274(7) 0.0506(2) Uani 1 1 d . . . . .
H2A H 0.8263(7) 0.2633(16) 0.5170(15) 0.076 Uiso 1 1 calc R U . . .
N1 N 0.26269(12) 0.24405(10) -0.43205(8) 0.0451(2) Uani 1 1 d . . . . .
C1 C 0.31745(14) 0.14911(9) 0.27601(9) 0.0361(2) Uani 1 1 d . . . . .
C2 C 0.49352(13) 0.18438(10) 0.37336(8) 0.0363(2) Uani 1 1 d . . . . .
H2 H 0.510177 0.209016 0.46184 0.044 Uiso 1 1 calc R U . . .
C3 C 0.64537(14) 0.18345(10) 0.34065(9) 0.0391(2) Uani 1 1 d . . . . .
C4 C 0.61979(16) 0.14406(11) 0.20958(10) 0.0455(2) Uani 1 1 d . . . . .
H4 H 0.720975 0.141723 0.186585 0.055 Uiso 1 1 calc R U . . .
C5 C 0.44333(17) 0.10855(12) 0.11418(10) 0.0486(3) Uani 1 1 d . . . . .
H5 H 0.425732 0.082135 0.025769 0.058 Uiso 1 1 calc R U . . .
C6 C 0.29160(16) 0.11079(11) 0.14514(9) 0.0441(2) Uani 1 1 d . . . . .
H6 H 0.17283 0.086736 0.078654 0.053 Uiso 1 1 calc R U . . .
C7 C 0.19719(15) 0.14689(12) -0.35695(10) 0.0441(2) Uani 1 1 d . . . . .
H7 H 0.154771 0.042739 -0.386203 0.053 Uiso 1 1 calc R U . . .
C8 C 0.18877(14) 0.19182(11) -0.23887(10) 0.0416(2) Uani 1 1 d . . . . .
H8 H 0.140499 0.119174 -0.189723 0.05 Uiso 1 1 calc R U . . .
C9 C 0.25210(13) 0.34530(11) -0.19268(9) 0.0382(2) Uani 1 1 d D U . . .
C10 C 0.32581(15) 0.44735(11) -0.26849(10) 0.0446(2) Uani 1 1 d . . . . .
H10 H 0.374461 0.552544 -0.239885 0.053 Uiso 1 1 calc R U . . .
C11 C 0.32642(15) 0.39191(12) -0.38609(10) 0.0470(2) Uani 1 1 d . . . . .
H11 H 0.374435 0.462003 -0.437169 0.056 Uiso 1 1 calc R U . . .
C12 C 0.2203(11) 0.3800(6) -0.0660(6) 0.0318(8) Uani 0.506(10) 1 d D U P A 1
H12 H 0.165597 0.298722 -0.025976 0.038 Uiso 0.506(10) 1 calc R U P A 1
C13 C 0.2661(4) 0.5185(5) -0.0109(3) 0.0317(7) Uani 0.506(10) 1 d D U P A 1
H13 H 0.326138 0.598222 -0.050548 0.038 Uiso 0.506(10) 1 calc R U P A 1
C14A C 0.2314(11) 0.5620(7) 0.1106(5) 0.0299(10) Uani 0.506(10) 1 d G U P A 1
C15A C 0.1488(12) 0.4535(6) 0.1789(7) 0.0369(11) Uani 0.506(10) 1 d G U P A 1
H15A H 0.113263 0.350514 0.150276 0.044 Uiso 0.506(10) 1 calc R U P A 1
C16A C 0.1187(12) 0.4972(7) 0.2897(7) 0.0382(13) Uani 0.506(10) 1 d G U P A 1
H16A H 0.062834 0.423865 0.33589 0.046 Uiso 0.506(10) 1 calc R U P A 1
N2A N 0.1713(12) 0.6495(8) 0.3321(6) 0.0356(13) Uani 0.506(10) 1 d G U P A 1
C17A C 0.2539(12) 0.7580(6) 0.2637(6) 0.0354(11) Uani 0.506(10) 1 d G U P A 1
H17A H 0.289461 0.860983 0.292373 0.043 Uiso 0.506(10) 1 calc R U P A 1
C18A C 0.2840(11) 0.7143(6) 0.1530(6) 0.0346(10) Uani 0.506(10) 1 d G U P A 1
H18A H 0.339891 0.787636 0.106759 0.041 Uiso 0.506(10) 1 calc R U P A 1
C14B C 0.2164(13) 0.5269(9) 0.1213(6) 0.0391(13) Uani 0.494(10) 1 d . U P A 2
C15B C 0.1277(14) 0.4432(7) 0.2017(8) 0.0437(12) Uani 0.494(10) 1 d . U P A 2
H15B H 0.078375 0.33674 0.186488 0.052 Uiso 0.494(10) 1 calc R U P A 2
C16B C 0.1131(14) 0.5182(9) 0.3034(8) 0.0424(12) Uani 0.494(10) 1 d . U P A 2
H16B H 0.05071 0.457267 0.354829 0.051 Uiso 0.494(10) 1 calc R U P A 2
N2B N 0.1753(14) 0.6628(10) 0.3366(7) 0.0477(16) Uani 0.494(10) 1 d . U P A 2
C17B C 0.2574(14) 0.7373(9) 0.2606(8) 0.0455(13) Uani 0.494(10) 1 d . U P A 2
H17B H 0.307143 0.843678 0.281297 0.055 Uiso 0.494(10) 1 calc R U P A 2
C18B C 0.2814(12) 0.6823(8) 0.1543(7) 0.0388(11) Uani 0.494(10) 1 d . U P A 2
H18B H 0.340712 0.748301 0.104432 0.047 Uiso 0.494(10) 1 calc R U P A 2
C19 C 0.2500(12) 0.4114(9) -0.0804(8) 0.0461(13) Uani 0.494(10) 1 d D U P A 2
C20 C 0.2353(6) 0.4634(8) 0.0145(4) 0.0467(9) Uani 0.494(10) 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   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 1.3587(12) . ?
O1 H1 0.977(15) . ?
O2 C3 1.3560(12) . ?
O2 H2A 0.975(16) . ?
N1 C7 1.3362(14) . ?
N1 C11 1.3387(14) . ?
C1 C2 1.3884(13) . ?
C1 C6 1.3905(13) . ?
C2 C3 1.3908(13) . ?
C2 H2 0.94 . ?
C3 C4 1.3950(13) . ?
C4 C5 1.3809(16) . ?
C4 H4 0.94 . ?
C5 C6 1.3846(15) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3761(14) . ?
C7 H7 0.94 . ?
C8 C9 1.3904(13) . ?
C8 H8 0.94 . ?
C9 C19 1.371(8) . ?
C9 C10 1.3899(14) . ?
C9 C12 1.533(6) . ?
C10 C11 1.3761(15) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.316(7) . ?
C12 H12 0.94 . ?
C13 C14A 1.518(5) . ?
C13 H13 0.94 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.94 . ?
C16A N2A 1.39 . ?
C16A H16A 0.94 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.94 . ?
C18A H18A 0.94 . ?
C14B C20 1.379(6) . ?
C14B C18B 1.384(5) . ?
C14B C15B 1.389(6) . ?
C15B C16B 1.370(5) . ?
C15B H15B 0.94 . ?
C16B N2B 1.289(5) . ?
C16B H16B 0.94 . ?
N2B C17B 1.288(5) . ?
C17B C18B 1.361(4) . ?
C17B H17B 0.94 . ?
C18B H18B 0.94 . ?
C19 C20 1.196(8) . ?

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 . . ?
C7 N1 C11 116.90(8) . . ?
O1 C1 C2 121.69(8) . . ?
O1 C1 C6 118.35(9) . . ?
C2 C1 C6 119.96(9) . . ?
C1 C2 C3 120.35(8) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.03(8) . . ?
O2 C3 C4 118.05(9) . . ?
C2 C3 C4 119.92(9) . . ?
C5 C4 C3 118.89(10) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.83(9) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.04(9) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.22(9) . . ?
N1 C7 H7 118.4 . . ?
C8 C7 H7 118.4 . . ?
C7 C8 C9 119.61(9) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C19 C9 C10 114.4(3) . . ?
C19 C9 C8 128.2(3) . . ?
C10 C9 C8 117.41(9) . . ?
C10 C9 C12 127.7(2) . . ?
C8 C9 C12 114.8(2) . . ?
C11 C10 C9 118.93(9) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N1 C11 C10 123.87(9) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13 C12 C9 122.9(5) . . ?
C13 C12 H12 118.6 . . ?
C9 C12 H12 118.6 . . ?
C12 C13 C14A 126.3(5) . . ?
C12 C13 H13 116.9 . . ?
C14A C13 H13 116.9 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13 121.5(3) . . ?
C18A C14A C13 118.5(3) . . ?
C14A C15A C16A 120 . . ?
C14A C15A H15A 120 . . ?
C16A C15A H15A 120 . . ?
C15A C16A N2A 120 . . ?
C15A C16A H16A 120 . . ?
N2A C16A H16A 120 . . ?
C17A N2A C16A 120 . . ?
N2A C17A C18A 120 . . ?
N2A C17A H17A 120 . . ?
C18A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C20 C14B C18B 121.5(5) . . ?
C20 C14B C15B 124.1(4) . . ?
C18B C14B C15B 114.4(3) . . ?
C16B C15B C14B 119.1(3) . . ?
C16B C15B H15B 120.5 . . ?
C14B C15B H15B 120.5 . . ?
N2B C16B C15B 127.3(4) . . ?
N2B C16B H16B 116.4 . . ?
C15B C16B H16B 116.4 . . ?
C17B N2B C16B 112.3(4) . . ?
N2B C17B C18B 128.5(4) . . ?
N2B C17B H17B 115.7 . . ?
C18B C17B H17B 115.7 . . ?
C17B C18B C14B 118.5(3) . . ?
C17B C18B H18B 120.8 . . ?
C14B C18B H18B 120.8 . . ?
C20 C19 C9 175.7(8) . . ?
C19 C20 C14B 178.0(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 0.98 1.77 2.7427(11) 174.9 1_556 yes
O2 H2A N2A^a 0.97 1.82 2.79(3) 176 2_666 yes
O2 H2A N2B^b 0.97 1.73 2.708(6) 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_BE50_BA50_230
_database_code_depnum_ccdc_archive 'CCDC 1995695'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT911_BE50_BA50_230       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2020-04-01T17:47:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C18 H15.02 N2 O2'
_chemical_formula_weight         291.34

#----------------------------------------------------------------------------#
#                   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                   8.15433(11)
_cell_length_b                   9.85391(12)
_cell_length_c                   10.92795(12)
_cell_angle_alpha                92.5643(9)
_cell_angle_beta                 107.7884(11)
_cell_angle_gamma                114.4264(12)
_cell_volume                     746.298(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    17826
_cell_measurement_theta_min      4.317
_cell_measurement_theta_max      77.168

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

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.088
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             307
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 2 0.1024
-2 2 -6 0.081
-4 -1 0 0.0438
5 -1 -3 0.0658
1 -6 4 0.0337
4 1 0 0.0468
-2 -4 4 0.0464
-5 0 4 0.0804
-5 1 -1 0.0444
-3 2 -4 0.0582
-1 -5 -1 0.0561
1 5 1 0.0835
5 -3 0 0.0435
-2 6 2 0.0954
4 -6 1 0.0427
0 -6 2 0.0367
-2 -5 3 0.0426
2 4 -3 0.0582
-1 -1 7 0.0957
-4 -2 1 0.0435
-1 6 0 0.0733
-2 4 -5 0.054
4 2 -4 0.0654
-1 5 -4 0.0508

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

_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.83593
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.888
_shelx_estimated_absorpt_T_max   0.956

#----------------------------------------------------------------------------#
#                   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      0.0601106
_diffrn_orient_matrix_ub_12      0.0567015
_diffrn_orient_matrix_ub_13      0.1479002
_diffrn_orient_matrix_ub_21      -0.0022293
_diffrn_orient_matrix_ub_22      -0.1527905
_diffrn_orient_matrix_ub_23      0.0268467
_diffrn_orient_matrix_ub_31      0.2137622
_diffrn_orient_matrix_ub_32      0.0641765
_diffrn_orient_matrix_ub_33      0.0145752
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_number            28336
_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         77.38
_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             3095
_reflns_number_gt                2836
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_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)+(0.0481P)²+0.0823P] 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(7)
_refine_ls_number_reflns         3095
_refine_ls_number_parameters     284
_refine_ls_number_restraints     567
_refine_ls_R_factor_all          0.036
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0939
_refine_ls_wR_factor_gt          0.0919
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      0.984
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.028

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

_refine_special_details          
;
 To help model the substitution of the bis(4-pyridyl)acetylene with 
 1,2-bis(4-pyridyl)ethylene, the atom sites N2 and  C12 < C18, were split into
 parts A and B. The site associated with the rings were allowed to free refine
 their site occupancies to a total value of 1.0, while the C12 and C13 sites 
 were constrained to 0.51 and C19 and C20 (acetyl moiety) were constrained to
 0.49. To help maintain reasonable ADP and bond lengths, SIMU, RIGU, and DFIX 
 restraints and constraints were applied. At this temperature the ratio of the
 disordered BPE sites (A and B) were 0.48 and 0.03, 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 0.16744(10) 0.14968(8) 0.30459(7) 0.04860(19) Uani 1 1 d . . . . .
H1 H 0.200304 0.175392 0.385044 0.073 Uiso 1 1 calc R U . . .
O2 O 0.81993(11) 0.22055(10) 0.43230(7) 0.0559(2) Uani 1 1 d . . . . .
H2A H 0.825027 0.257282 0.503991 0.084 Uiso 1 1 calc R U . . .
N1 N 0.26241(13) 0.24357(11) -0.43208(8) 0.0494(2) Uani 1 1 d . . . . .
C1 C 0.31776(14) 0.14865(10) 0.27602(9) 0.0396(2) Uani 1 1 d . . . . .
C2 C 0.49325(14) 0.18396(10) 0.37312(9) 0.0398(2) Uani 1 1 d . . . . .
H2 H 0.509783 0.208476 0.461578 0.048 Uiso 1 1 calc R U . . .
C3 C 0.64496(15) 0.18334(11) 0.34047(9) 0.0429(2) Uani 1 1 d . . . . .
C4 C 0.61940(17) 0.14404(12) 0.20942(10) 0.0500(3) Uani 1 1 d . . . . .
H4 H 0.720336 0.141691 0.186342 0.06 Uiso 1 1 calc R U . . .
C5 C 0.44362(18) 0.10870(12) 0.11432(10) 0.0532(3) Uani 1 1 d . . . . .
H5 H 0.426273 0.08264 0.025908 0.064 Uiso 1 1 calc R U . . .
C6 C 0.29210(16) 0.11046(11) 0.14511(10) 0.0483(2) Uani 1 1 d . . . . .
H6 H 0.173568 0.086223 0.078632 0.058 Uiso 1 1 calc R U . . .
C7 C 0.19719(15) 0.14713(12) -0.35687(10) 0.0484(2) Uani 1 1 d . . . . .
H7 H 0.154713 0.043003 -0.385992 0.058 Uiso 1 1 calc R U . . .
C8 C 0.18898(15) 0.19239(11) -0.23892(10) 0.0459(2) Uani 1 1 d . . . . .
H8 H 0.140844 0.120046 -0.189693 0.055 Uiso 1 1 calc R U . . .
C9 C 0.25232(14) 0.34580(11) -0.19294(9) 0.0421(2) Uani 1 1 d D U . . .
C10 C 0.32586(15) 0.44726(12) -0.26884(11) 0.0491(2) Uani 1 1 d . . . . .
H10 H 0.374576 0.552418 -0.240362 0.059 Uiso 1 1 calc R U . . .
C11 C 0.32627(16) 0.39145(13) -0.38627(11) 0.0514(3) Uani 1 1 d . . . . .
H11 H 0.374209 0.461226 -0.437419 0.062 Uiso 1 1 calc R U . . .
C12A C 0.2199(13) 0.3786(7) -0.0661(7) 0.0363(10) Uani 0.477(3) 1 d D U P A 1
H12A H 0.165795 0.297394 -0.026132 0.044 Uiso 0.477(3) 1 calc R U P A 1
C13A C 0.2663(4) 0.5190(3) -0.0111(3) 0.0342(6) Uani 0.477(3) 1 d D U P A 1
H13A H 0.325045 0.598314 -0.051351 0.041 Uiso 0.477(3) 1 calc R U P A 1
C12B C 0.264(10) 0.453(2) -0.086(4) 0.044(3) Uani 0.033(3) 1 d D U P A 2
H12B H 0.328439 0.557075 -0.086519 0.053 Uiso 0.033(3) 1 calc R U P A 2
C13B C 0.197(6) 0.4215(19) 0.008(4) 0.040(4) Uani 0.033(3) 1 d D U P A 2
H13B H 0.126959 0.317293 0.005877 0.048 Uiso 0.033(3) 1 calc R U P A 2
C14A C 0.2330(12) 0.5621(7) 0.1104(6) 0.0329(10) Uani 0.477(3) 1 d DG U P A 1
C15A C 0.1499(13) 0.4536(6) 0.1783(7) 0.0403(12) Uani 0.477(3) 1 d G U P A 1
H15A H 0.114724 0.350805 0.149655 0.048 Uiso 0.477(3) 1 calc R U P A 1
C16A C 0.1188(14) 0.4973(8) 0.2886(7) 0.0407(13) Uani 0.477(3) 1 d G U P A 1
H16A H 0.062641 0.423897 0.334553 0.049 Uiso 0.477(3) 1 calc R U P A 1
N2A N 0.1709(14) 0.6493(9) 0.3310(7) 0.0395(15) Uani 0.477(3) 1 d G U P A 1
C17A C 0.2540(13) 0.7578(7) 0.2631(7) 0.0391(11) Uani 0.477(3) 1 d G U P A 1
H17A H 0.289203 0.860649 0.291733 0.047 Uiso 0.477(3) 1 calc R U P A 1
C18A C 0.2851(12) 0.7142(6) 0.1528(7) 0.0384(11) Uani 0.477(3) 1 d G U P A 1
H18A H 0.341287 0.78756 0.106834 0.046 Uiso 0.477(3) 1 calc R U P A 1
C14B C 0.2148(12) 0.5268(7) 0.1210(6) 0.0422(12) Uani 0.523(3) 1 d D U P A 2
C15B C 0.1280(13) 0.4432(7) 0.2014(7) 0.0470(11) Uani 0.523(3) 1 d . U P A 2
H15B H 0.079343 0.336869 0.185808 0.056 Uiso 0.523(3) 1 calc R U P A 2
C16B C 0.1139(14) 0.5174(9) 0.3043(8) 0.0468(12) Uani 0.523(3) 1 d . U P A 2
H16B H 0.052587 0.456373 0.355851 0.056 Uiso 0.523(3) 1 calc R U P A 2
N2B N 0.1760(14) 0.6619(9) 0.3375(7) 0.0506(16) Uani 0.523(3) 1 d . U P A 2
C17B C 0.2567(14) 0.7371(8) 0.2613(8) 0.0508(13) Uani 0.523(3) 1 d . U P A 2
H17B H 0.305444 0.843294 0.281919 0.061 Uiso 0.523(3) 1 calc R U P A 2
C18B C 0.2803(11) 0.6820(7) 0.1544(7) 0.0439(11) Uani 0.523(3) 1 d . U P A 2
H18B H 0.339753 0.747874 0.104652 0.053 Uiso 0.523(3) 1 calc R U P A 2
C19 C 0.2487(12) 0.4102(7) -0.0793(7) 0.0475(13) Uani 0.49 1 d D U P A 2
C20 C 0.2370(6) 0.4653(5) 0.0140(4) 0.0502(7) Uani 0.49 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   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(12) . ?
O1 H1 0.83 . ?
O2 C3 1.3552(12) . ?
O2 H2A 0.83 . ?
N1 C7 1.3343(14) . ?
N1 C11 1.3391(14) . ?
C1 C2 1.3864(14) . ?
C1 C6 1.3913(13) . ?
C2 C3 1.3904(14) . ?
C2 H2 0.94 . ?
C3 C4 1.3949(13) . ?
C4 C5 1.3786(16) . ?
C4 H4 0.94 . ?
C5 C6 1.3825(16) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3751(14) . ?
C7 H7 0.94 . ?
C8 C9 1.3900(14) . ?
C8 H8 0.94 . ?
C9 C19 1.383(7) . ?
C9 C10 1.3890(15) . ?
C9 C12B 1.496(19) . ?
C9 C12A 1.533(6) . ?
C10 C11 1.3749(15) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12A C13A 1.331(7) . ?
C12A H12A 0.94 . ?
C13A C14A 1.510(5) . ?
C13A H13A 0.94 . ?
C12B C13B 1.298(19) . ?
C12B H12B 0.94 . ?
C13B C14B 1.505(19) . ?
C13B H13B 0.94 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.94 . ?
C16A N2A 1.39 . ?
C16A H16A 0.94 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.94 . ?
C18A H18A 0.94 . ?
C14B C18B 1.382(5) . ?
C14B C15B 1.383(5) . ?
C14B C20 1.388(6) . ?
C15B C16B 1.373(5) . ?
C15B H15B 0.94 . ?
C16B N2B 1.288(4) . ?
C16B H16B 0.94 . ?
N2B C17B 1.290(4) . ?
C17B C18B 1.366(4) . ?
C17B H17B 0.94 . ?
C18B H18B 0.94 . ?
C19 C20 1.181(8) . ?

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 . . ?
C7 N1 C11 116.84(9) . . ?
O1 C1 C2 121.85(8) . . ?
O1 C1 C6 118.23(9) . . ?
C2 C1 C6 119.92(9) . . ?
C1 C2 C3 120.42(8) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.17(8) . . ?
O2 C3 C4 117.99(9) . . ?
C2 C3 C4 119.84(9) . . ?
C5 C4 C3 118.88(10) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.95(9) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.98(10) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.31(9) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.58(9) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C19 C9 C10 115.5(3) . . ?
C19 C9 C8 127.2(3) . . ?
C10 C9 C8 117.39(9) . . ?
C19 C9 C12B 15.5(5) . . ?
C10 C9 C12B 100.1(6) . . ?
C8 C9 C12B 142.5(7) . . ?
C10 C9 C12A 128.5(2) . . ?
C8 C9 C12A 114.0(2) . . ?
C11 C10 C9 118.96(10) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N1 C11 C10 123.87(10) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13A C12A C9 121.8(4) . . ?
C13A C12A H12A 119.1 . . ?
C9 C12A H12A 119.1 . . ?
C12A C13A C14A 125.8(4) . . ?
C12A C13A H13A 117.1 . . ?
C14A C13A H13A 117.1 . . ?
C13B C12B C9 128.5(17) . . ?
C13B C12B H12B 115.8 . . ?
C9 C12B H12B 115.8 . . ?
C12B C13B C14B 129.6(15) . . ?
C12B C13B H13B 115.2 . . ?
C14B C13B H13B 115.2 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13A 121.6(3) . . ?
C18A C14A C13A 118.4(3) . . ?
C14A C15A C16A 120 . . ?
C14A C15A H15A 120 . . ?
C16A C15A H15A 120 . . ?
N2A C16A C15A 120 . . ?
N2A C16A H16A 120 . . ?
C15A C16A H16A 120 . . ?
C16A N2A C17A 120 . . ?
N2A C17A C18A 120 . . ?
N2A C17A H17A 120 . . ?
C18A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C15B 114.7(3) . . ?
C18B C14B C20 120.6(5) . . ?
C15B C14B C20 124.7(4) . . ?
C18B C14B C13B 135.1(10) . . ?
C15B C14B C13B 109.9(8) . . ?
C20 C14B C13B 15.5(5) . . ?
C16B C15B C14B 119.2(3) . . ?
C16B C15B H15B 120.4 . . ?
C14B C15B H15B 120.4 . . ?
N2B C16B C15B 126.8(3) . . ?
N2B C16B H16B 116.6 . . ?
C15B C16B H16B 116.6 . . ?
C16B N2B C17B 112.7(3) . . ?
N2B C17B C18B 128.2(4) . . ?
N2B C17B H17B 115.9 . . ?
C18B C17B H17B 115.9 . . ?
C17B C18B C14B 118.4(3) . . ?
C17B C18B H18B 120.8 . . ?
C14B C18B H18B 120.8 . . ?
C20 C19 C9 176.6(9) . . ?
C19 C20 C14B 177.6(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 1.92 2.7466(11) 175.1 1_556 yes
O2 H2A N2A^a 0.83 1.97 2.80(3) 176.7 2_666 yes
O2 H2A N2B^b 0.83 1.88 2.707(6) 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_BE50_BA50_270
_database_code_depnum_ccdc_archive 'CCDC 1995697'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT911_BE50_BA50_270       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         11 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2020-04-01T17:48:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C18 H15.02 N2 O2'
_chemical_formula_weight         291.34

#----------------------------------------------------------------------------#
#                   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                   8.18944(9)
_cell_length_b                   9.87060(10)
_cell_length_c                   10.93717(11)
_cell_angle_alpha                92.7279(8)
_cell_angle_beta                 107.7404(9)
_cell_angle_gamma                114.3479(10)
_cell_volume                     751.727(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    16506
_cell_measurement_theta_min      4.314
_cell_measurement_theta_max      76.821

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

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.088
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             307
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 2 0.1024
-2 2 -6 0.081
-4 -1 0 0.0438
5 -1 -3 0.0658
1 -6 4 0.0337
4 1 0 0.0468
-2 -4 4 0.0464
-5 0 4 0.0804
-5 1 -1 0.0444
-3 2 -4 0.0582
-1 -5 -1 0.0561
1 5 1 0.0835
5 -3 0 0.0435
-2 6 2 0.0954
4 -6 1 0.0427
0 -6 2 0.0367
-2 -5 3 0.0426
3 4 -3 0.0582
-1 -1 7 0.0957
-4 -2 1 0.0435
-1 6 0 0.0733
-2 4 -5 0.054
4 2 -4 0.0654
-1 5 -4 0.0508

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

_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.77118
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.956

#----------------------------------------------------------------------------#
#                   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      0.0605864
_diffrn_orient_matrix_ub_12      0.0567472
_diffrn_orient_matrix_ub_13      0.1479403
_diffrn_orient_matrix_ub_21      -0.0025673
_diffrn_orient_matrix_ub_22      -0.1526726
_diffrn_orient_matrix_ub_23      0.0263459
_diffrn_orient_matrix_ub_31      0.2125083
_diffrn_orient_matrix_ub_32      0.0635357
_diffrn_orient_matrix_ub_33      0.0140761
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_number            28258
_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         4.331
_diffrn_reflns_theta_max         77.38
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.965
_reflns_Friedel_coverage         0
_reflns_number_total             3094
_reflns_number_gt                2770
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_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)+(0.0532P)²+0.0526P] 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(8)
_refine_ls_number_reflns         3094
_refine_ls_number_parameters     284
_refine_ls_number_restraints     567
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.115
_refine_diff_density_rms         0.027

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

_refine_special_details          
;
 To help model the substitution of the bis(4-pyridyl)acetylene with 
 1,2-bis(4-pyridyl)ethylene, the atom sites N2 and  C12 < C18, were split into
 parts A and B. The site associated with the rings were allowed to free refine
 their site occupancies to a total value of 1.0, while the C12 and C13 sites 
 were constrained to 0.51 and C19 and C20 (acetyl moiety) were constrained to
 0.49. To help maintain reasonable ADP and bond lengths, SIMU, RIGU, and DFIX 
 restraints and constraints were applied. At this temperature the ratio of the
 disordered BPE sites (A and B) were 0.44 and 0.07, 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 0.16832(10) 0.14806(9) 0.30449(7) 0.0586(2) Uani 1 1 d . . . . .
H1 H 0.20096 0.174693 0.383823 0.088 Uiso 1 1 calc R U . . .
O2 O 0.81797(11) 0.22017(10) 0.43166(7) 0.0669(2) Uani 1 1 d . . . . .
H2A H 0.822834 0.256186 0.502556 0.1 Uiso 1 1 calc R U . . .
N1 N 0.26200(13) 0.24281(11) -0.43200(8) 0.0586(2) Uani 1 1 d . . . . .
C1 C 0.31831(14) 0.14752(10) 0.27600(9) 0.0471(2) Uani 1 1 d . . . . .
C2 C 0.49288(14) 0.18303(10) 0.37285(9) 0.0472(2) Uani 1 1 d . . . . .
H2 H 0.509132 0.207174 0.460348 0.057 Uiso 1 1 calc R U . . .
C3 C 0.64393(15) 0.18281(11) 0.34010(9) 0.0508(2) Uani 1 1 d . . . . .
C4 C 0.61854(18) 0.14387(12) 0.20914(10) 0.0595(3) Uani 1 1 d . . . . .
H4 H 0.718004 0.141792 0.186184 0.071 Uiso 1 1 calc R U . . .
C5 C 0.44387(19) 0.10857(13) 0.11444(10) 0.0633(3) Uani 1 1 d . . . . .
H5 H 0.426885 0.08309 0.02697 0.076 Uiso 1 1 calc R U . . .
C6 C 0.29301(17) 0.10980(12) 0.14527(10) 0.0574(3) Uani 1 1 d . . . . .
H6 H 0.176259 0.085759 0.079562 0.069 Uiso 1 1 calc R U . . .
C7 C 0.19711(16) 0.14774(12) -0.35664(10) 0.0576(3) Uani 1 1 d . . . . .
H7 H 0.154797 0.04472 -0.385174 0.069 Uiso 1 1 calc R U . . .
C8 C 0.18938(16) 0.19378(12) -0.23911(10) 0.0550(3) Uani 1 1 d . . . . .
H8 H 0.141948 0.122866 -0.190216 0.066 Uiso 1 1 calc R U . . .
C9 C 0.25281(14) 0.34689(12) -0.19367(9) 0.0500(2) Uani 1 1 d D U . . .
C10 C 0.32584(16) 0.44698(12) -0.26977(11) 0.0583(3) Uani 1 1 d . . . . .
H10 H 0.374112 0.550969 -0.241914 0.07 Uiso 1 1 calc R U . . .
C11 C 0.32590(16) 0.39044(13) -0.38679(11) 0.0609(3) Uani 1 1 d . . . . .
H11 H 0.373118 0.458771 -0.437605 0.073 Uiso 1 1 calc R U . . .
C12A C 0.2187(14) 0.3790(7) -0.0670(7) 0.0432(11) Uani 0.443(3) 1 d D U P A 1
H12A H 0.163093 0.298339 -0.028722 0.052 Uiso 0.443(3) 1 calc R U P A 1
C13A C 0.2664(5) 0.5185(3) -0.0109(3) 0.0401(6) Uani 0.443(3) 1 d D U P A 1
H13A H 0.326013 0.596927 -0.049816 0.048 Uiso 0.443(3) 1 calc R U P A 1
C12B C 0.262(6) 0.4531(18) -0.086(2) 0.052(3) Uani 0.067(3) 1 d D U P A 2
H12B H 0.321957 0.555806 -0.087402 0.062 Uiso 0.067(3) 1 calc R U P A 2
C13B C 0.198(4) 0.4199(14) 0.008(2) 0.049(3) Uani 0.067(3) 1 d D U P A 2
H13B H 0.133743 0.316834 0.006856 0.059 Uiso 0.067(3) 1 calc R U P A 2
C14A C 0.2331(13) 0.5618(7) 0.1097(6) 0.0390(11) Uani 0.443(3) 1 d DG U P A 1
C15A C 0.1511(13) 0.4534(6) 0.1775(7) 0.0465(13) Uani 0.443(3) 1 d G U P A 1
H15A H 0.116333 0.351858 0.148786 0.056 Uiso 0.443(3) 1 calc R U P A 1
C16A C 0.1210(14) 0.4968(8) 0.2883(7) 0.0473(14) Uani 0.443(3) 1 d G U P A 1
H16A H 0.066094 0.424286 0.333695 0.057 Uiso 0.443(3) 1 calc R U P A 1
N2A N 0.1729(14) 0.6486(9) 0.3313(7) 0.0468(16) Uani 0.443(3) 1 d G U P A 1
C17A C 0.2549(14) 0.7570(7) 0.2635(8) 0.0479(13) Uani 0.443(3) 1 d G U P A 1
H17A H 0.289656 0.858508 0.292281 0.057 Uiso 0.443(3) 1 calc R U P A 1
C18A C 0.2850(13) 0.7136(6) 0.1527(7) 0.0471(12) Uani 0.443(3) 1 d G U P A 1
H18A H 0.339896 0.786084 0.107371 0.057 Uiso 0.443(3) 1 calc R U P A 1
C14B C 0.2139(11) 0.5251(6) 0.1211(6) 0.0495(12) Uani 0.557(3) 1 d D U P A 2
C15B C 0.1273(11) 0.4422(7) 0.2014(7) 0.0547(11) Uani 0.557(3) 1 d . U P A 2
H15B H 0.078768 0.337099 0.185889 0.066 Uiso 0.557(3) 1 calc R U P A 2
C16B C 0.1138(13) 0.5167(8) 0.3043(7) 0.0549(11) Uani 0.557(3) 1 d . U P A 2
H16B H 0.05406 0.45708 0.355793 0.066 Uiso 0.557(3) 1 calc R U P A 2
N2B N 0.1756(13) 0.6613(9) 0.3367(7) 0.0591(15) Uani 0.557(3) 1 d . U P A 2
C17B C 0.2565(13) 0.7362(7) 0.2604(8) 0.0610(13) Uani 0.557(3) 1 d . U P A 2
H17B H 0.305206 0.841155 0.280768 0.073 Uiso 0.557(3) 1 calc R U P A 2
C18B C 0.2789(10) 0.6799(6) 0.1540(7) 0.0532(11) Uani 0.557(3) 1 d . U P A 2
H18B H 0.336872 0.744271 0.104327 0.064 Uiso 0.557(3) 1 calc R U P A 2
C19 C 0.2504(12) 0.4103(8) -0.0784(8) 0.0572(15) Uani 0.49 1 d D U P A 2
C20 C 0.2364(6) 0.4646(6) 0.0132(4) 0.0600(9) Uani 0.49 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   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(12) . ?
O1 H1 0.82 . ?
O2 C3 1.3536(13) . ?
O2 H2A 0.82 . ?
N1 C7 1.3311(14) . ?
N1 C11 1.3367(15) . ?
C1 C2 1.3847(14) . ?
C1 C6 1.3896(13) . ?
C2 C3 1.3894(14) . ?
C2 H2 0.93 . ?
C3 C4 1.3938(14) . ?
C4 C5 1.3756(17) . ?
C4 H4 0.93 . ?
C5 C6 1.3806(17) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.3713(14) . ?
C7 H7 0.93 . ?
C8 C9 1.3873(14) . ?
C8 H8 0.93 . ?
C9 C10 1.3860(16) . ?
C9 C19 1.390(8) . ?
C9 C12B 1.500(17) . ?
C9 C12A 1.538(7) . ?
C10 C11 1.3719(16) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12A C13A 1.325(8) . ?
C12A H12A 0.93 . ?
C13A C14A 1.504(6) . ?
C13A H13A 0.93 . ?
C12B C13B 1.291(18) . ?
C12B H12B 0.93 . ?
C13B C14B 1.513(17) . ?
C13B H13B 0.93 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.93 . ?
C16A N2A 1.39 . ?
C16A H16A 0.93 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.93 . ?
C18A H18A 0.93 . ?
C14B C18B 1.381(4) . ?
C14B C15B 1.384(5) . ?
C14B C20 1.393(6) . ?
C15B C16B 1.372(5) . ?
C15B H15B 0.93 . ?
C16B N2B 1.291(4) . ?
C16B H16B 0.93 . ?
N2B C17B 1.293(4) . ?
C17B C18B 1.361(4) . ?
C17B H17B 0.93 . ?
C18B H18B 0.93 . ?
C19 C20 1.172(8) . ?

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 . . ?
C7 N1 C11 116.81(9) . . ?
O1 C1 C2 121.93(8) . . ?
O1 C1 C6 118.16(9) . . ?
C2 C1 C6 119.91(10) . . ?
C1 C2 C3 120.40(9) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.17(8) . . ?
O2 C3 C4 118.01(9) . . ?
C2 C3 C4 119.82(10) . . ?
C5 C4 C3 118.87(10) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.01(9) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.98(10) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.42(10) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.54(10) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 117.35(9) . . ?
C10 C9 C19 116.5(3) . . ?
C8 C9 C19 126.2(3) . . ?
C10 C9 C12B 101.0(6) . . ?
C8 C9 C12B 141.5(6) . . ?
C19 C9 C12B 15.8(5) . . ?
C10 C9 C12A 129.2(2) . . ?
C8 C9 C12A 113.3(2) . . ?
C11 C10 C9 119.04(10) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N1 C11 C10 123.79(10) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13A C12A C9 121.7(4) . . ?
C13A C12A H12A 119.1 . . ?
C9 C12A H12A 119.1 . . ?
C12A C13A C14A 126.0(4) . . ?
C12A C13A H13A 117 . . ?
C14A C13A H13A 117 . . ?
C13B C12B C9 128.2(14) . . ?
C13B C12B H12B 115.9 . . ?
C9 C12B H12B 115.9 . . ?
C12B C13B C14B 129.1(12) . . ?
C12B C13B H13B 115.4 . . ?
C14B C13B H13B 115.4 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13A 121.3(4) . . ?
C18A C14A C13A 118.7(4) . . ?
C16A C15A C14A 120 . . ?
C16A C15A H15A 120 . . ?
C14A C15A H15A 120 . . ?
C15A C16A N2A 120 . . ?
C15A C16A H16A 120 . . ?
N2A C16A H16A 120 . . ?
C16A N2A C17A 120 . . ?
N2A C17A C18A 120 . . ?
N2A C17A H17A 120 . . ?
C18A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C15B 114.8(3) . . ?
C18B C14B C20 119.8(4) . . ?
C15B C14B C20 125.4(4) . . ?
C18B C14B C13B 134.6(7) . . ?
C15B C14B C13B 110.3(6) . . ?
C20 C14B C13B 15.5(5) . . ?
C16B C15B C14B 119.3(3) . . ?
C16B C15B H15B 120.4 . . ?
C14B C15B H15B 120.4 . . ?
N2B C16B C15B 126.5(3) . . ?
N2B C16B H16B 116.8 . . ?
C15B C16B H16B 116.8 . . ?
C16B N2B C17B 113.0(3) . . ?
N2B C17B C18B 127.8(4) . . ?
N2B C17B H17B 116.1 . . ?
C18B C17B H17B 116.1 . . ?
C17B C18B C14B 118.6(3) . . ?
C17B C18B H18B 120.7 . . ?
C14B C18B H18B 120.7 . . ?
C20 C19 C9 175.0(9) . . ?
C19 C20 C14B 178.2(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 0.82 1.93 2.7520(11) 175.4 1_556 yes
O2 H2A N2A^a 0.82 1.99 2.81(4) 176.4 2_666 yes
O2 H2A N2B^b 0.82 1.9 2.716(5) 177.8 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_BE50_BA50_250
_database_code_depnum_ccdc_archive 'CCDC 1995696'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT911_BE50_BA50_250       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2020-04-01T17:47:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C18 H15.02 N2 O2'
_chemical_formula_weight         291.34

#----------------------------------------------------------------------------#
#                   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                   8.17154(10)
_cell_length_b                   9.86186(11)
_cell_length_c                   10.93238(11)
_cell_angle_alpha                92.6441(8)
_cell_angle_beta                 107.7657(10)
_cell_angle_gamma                114.3850(11)
_cell_volume                     748.950(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    17184
_cell_measurement_theta_min      4.317
_cell_measurement_theta_max      76.985

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

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.088
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             307
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 2 0.1024
-2 2 -6 0.081
-4 -1 0 0.0438
5 -1 -3 0.0658
1 -6 4 0.0337
4 1 0 0.0468
-2 -4 4 0.0464
-5 0 4 0.0804
-5 1 -1 0.0444
-3 2 -4 0.0582
-1 -5 -1 0.0561
1 5 1 0.0835
5 -3 0 0.0435
-2 6 2 0.0954
4 -6 1 0.0427
0 -6 2 0.0367
-2 -5 3 0.0426
3 4 -3 0.0582
-1 -1 7 0.0957
-4 -2 1 0.0435
-1 6 0 0.0733
-2 4 -5 0.054
4 2 -4 0.0654
-1 5 -4 0.0508

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

_exptl_absorpt_coefficient_mu    0.69
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.76509
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.888
_shelx_estimated_absorpt_T_max   0.956

#----------------------------------------------------------------------------#
#                   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      0.0603556
_diffrn_orient_matrix_ub_12      0.0567377
_diffrn_orient_matrix_ub_13      0.14792
_diffrn_orient_matrix_ub_21      -0.0024073
_diffrn_orient_matrix_ub_22      -0.1527367
_diffrn_orient_matrix_ub_23      0.0266123
_diffrn_orient_matrix_ub_31      0.2131385
_diffrn_orient_matrix_ub_32      0.0638387
_diffrn_orient_matrix_ub_33      0.0143248
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_number            28234
_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         4.333
_diffrn_reflns_theta_max         77.258
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.97
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.97
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.97
_reflns_Friedel_coverage         0
_reflns_number_total             3093
_reflns_number_gt                2793
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_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)+(0.0522P)²+0.0606P] 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         3093
_refine_ls_number_parameters     284
_refine_ls_number_restraints     567
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.034
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.13
_refine_diff_density_rms         0.028

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

_refine_special_details          
;
 To help model the substitution of the bis(4-pyridyl)acetylene with 
 1,2-bis(4-pyridyl)ethylene, the atom sites N2 and  C12 < C18, were split into
 parts A and B. The site associated with the rings were allowed to free refine
 their site occupancies to a total value of 1.0, while the C12 and C13 sites 
 were constrained to 0.51 and C19 and C20 (acetyl moiety) were constrained to
 0.49. To help maintain reasonable ADP and bond lengths, SIMU, RIGU, and DFIX 
 restraints and constraints were applied. At this temperature the ratio of the
 disordered BPE sites (A and B) were 0.46 and 0.05, 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 0.16780(10) 0.14887(8) 0.30455(7) 0.0535(2) Uani 1 1 d . . . . .
H1 H 0.200748 0.175172 0.384933 0.08 Uiso 1 1 calc R U . . .
O2 O 0.81895(11) 0.22039(10) 0.43197(7) 0.0613(2) Uani 1 1 d . . . . .
H2A H 0.82395 0.25688 0.503726 0.092 Uiso 1 1 calc R U . . .
N1 N 0.26224(13) 0.24320(11) -0.43198(8) 0.0539(2) Uani 1 1 d . . . . .
C1 C 0.31803(14) 0.14813(10) 0.27600(9) 0.0432(2) Uani 1 1 d . . . . .
C2 C 0.49304(14) 0.18352(10) 0.37297(9) 0.0436(2) Uani 1 1 d . . . . .
H2 H 0.509498 0.207959 0.461418 0.052 Uiso 1 1 calc R U . . .
C3 C 0.64442(15) 0.18312(11) 0.34030(9) 0.0468(2) Uani 1 1 d . . . . .
C4 C 0.61909(17) 0.14404(12) 0.20927(10) 0.0548(3) Uani 1 1 d . . . . .
H4 H 0.719888 0.141894 0.186155 0.066 Uiso 1 1 calc R U . . .
C5 C 0.44379(18) 0.10865(12) 0.11432(10) 0.0582(3) Uani 1 1 d . . . . .
H5 H 0.426473 0.082668 0.025911 0.07 Uiso 1 1 calc R U . . .
C6 C 0.29266(16) 0.11020(11) 0.14522(10) 0.0527(3) Uani 1 1 d . . . . .
H6 H 0.174398 0.085975 0.078771 0.063 Uiso 1 1 calc R U . . .
C7 C 0.19711(15) 0.14734(12) -0.35684(10) 0.0531(3) Uani 1 1 d . . . . .
H7 H 0.154451 0.04321 -0.385864 0.064 Uiso 1 1 calc R U . . .
C8 C 0.18917(15) 0.19307(12) -0.23903(10) 0.0503(2) Uani 1 1 d . . . . .
H8 H 0.14113 0.12106 -0.189706 0.06 Uiso 1 1 calc R U . . .
C9 C 0.25250(14) 0.34623(11) -0.19331(9) 0.0459(2) Uani 1 1 d D U . . .
C10 C 0.32581(16) 0.44709(12) -0.26929(11) 0.0536(3) Uani 1 1 d . . . . .
H10 H 0.374546 0.552216 -0.240942 0.064 Uiso 1 1 calc R U . . .
C11 C 0.32608(16) 0.39100(13) -0.38651(11) 0.0563(3) Uani 1 1 d . . . . .
H11 H 0.373861 0.460435 -0.437771 0.068 Uiso 1 1 calc R U . . .
C12A C 0.2182(13) 0.3786(7) -0.0665(7) 0.0395(10) Uani 0.457(3) 1 d D U P A 1
H12A H 0.162062 0.297306 -0.027319 0.047 Uiso 0.457(3) 1 calc R U P A 1
C13A C 0.2663(5) 0.5187(3) -0.0114(3) 0.0368(6) Uani 0.457(3) 1 d D U P A 1
H13A H 0.326865 0.597853 -0.050911 0.044 Uiso 0.457(3) 1 calc R U P A 1
C12B C 0.266(7) 0.4530(18) -0.085(3) 0.048(3) Uani 0.053(3) 1 d D U P A 2
H12B H 0.332963 0.556881 -0.084333 0.058 Uiso 0.053(3) 1 calc R U P A 2
C13B C 0.198(4) 0.4218(15) 0.008(3) 0.043(3) Uani 0.053(3) 1 d D U P A 2
H13B H 0.12631 0.317688 0.004949 0.051 Uiso 0.053(3) 1 calc R U P A 2
C14A C 0.2319(12) 0.5621(6) 0.1095(6) 0.0354(10) Uani 0.457(3) 1 d DG U P A 1
C15A C 0.1499(12) 0.4533(6) 0.1772(7) 0.0421(12) Uani 0.457(3) 1 d G U P A 1
H15A H 0.114953 0.350626 0.14806 0.051 Uiso 0.457(3) 1 calc R U P A 1
C16A C 0.1195(13) 0.4962(8) 0.2880(7) 0.0437(13) Uani 0.457(3) 1 d G U P A 1
H16A H 0.063974 0.422533 0.333842 0.052 Uiso 0.457(3) 1 calc R U P A 1
N2A N 0.1711(14) 0.6479(9) 0.3312(6) 0.0428(14) Uani 0.457(3) 1 d G U P A 1
C17A C 0.2532(14) 0.7568(7) 0.2634(7) 0.0439(12) Uani 0.457(3) 1 d G U P A 1
H17A H 0.288083 0.859395 0.292594 0.053 Uiso 0.457(3) 1 calc R U P A 1
C18A C 0.2836(12) 0.7139(6) 0.1526(6) 0.0423(11) Uani 0.457(3) 1 d G U P A 1
H18A H 0.339063 0.787491 0.106811 0.051 Uiso 0.457(3) 1 calc R U P A 1
C14B C 0.2154(11) 0.5263(6) 0.1215(5) 0.0458(12) Uani 0.543(3) 1 d D U P A 2
C15B C 0.1283(12) 0.4432(7) 0.2022(7) 0.0507(11) Uani 0.543(3) 1 d . U P A 2
H15B H 0.079352 0.336884 0.186707 0.061 Uiso 0.543(3) 1 calc R U P A 2
C16B C 0.1142(12) 0.5176(8) 0.3046(7) 0.0497(11) Uani 0.543(3) 1 d . U P A 2
H16B H 0.053095 0.457172 0.356434 0.06 Uiso 0.543(3) 1 calc R U P A 2
N2B N 0.1767(13) 0.6626(9) 0.3370(6) 0.0548(15) Uani 0.543(3) 1 d . U P A 2
C17B C 0.2582(13) 0.7377(7) 0.2607(7) 0.0554(13) Uani 0.543(3) 1 d . U P A 2
H17B H 0.307448 0.843852 0.281113 0.066 Uiso 0.543(3) 1 calc R U P A 2
C18B C 0.2811(10) 0.6812(6) 0.1541(6) 0.0483(10) Uani 0.543(3) 1 d . U P A 2
H18B H 0.340263 0.746287 0.104081 0.058 Uiso 0.543(3) 1 calc R U P A 2
C19 C 0.2496(12) 0.4095(7) -0.0789(7) 0.0511(14) Uani 0.49 1 d D U P A 2
C20 C 0.2373(6) 0.4657(5) 0.0137(4) 0.0550(8) Uani 0.49 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   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 1.3585(12) . ?
O1 H1 0.83 . ?
O2 C3 1.3544(13) . ?
O2 H2A 0.83 . ?
N1 C7 1.3322(14) . ?
N1 C11 1.3383(14) . ?
C1 C2 1.3854(14) . ?
C1 C6 1.3902(13) . ?
C2 C3 1.3896(14) . ?
C2 H2 0.94 . ?
C3 C4 1.3949(13) . ?
C4 C5 1.3775(17) . ?
C4 H4 0.94 . ?
C5 C6 1.3818(16) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3740(14) . ?
C7 H7 0.94 . ?
C8 C9 1.3878(14) . ?
C8 H8 0.94 . ?
C9 C19 1.383(7) . ?
C9 C10 1.3879(15) . ?
C9 C12B 1.495(17) . ?
C9 C12A 1.541(6) . ?
C10 C11 1.3730(15) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12A C13A 1.326(7) . ?
C12A H12A 0.94 . ?
C13A C14A 1.510(5) . ?
C13A H13A 0.94 . ?
C12B C13B 1.297(18) . ?
C12B H12B 0.94 . ?
C13B C14B 1.504(17) . ?
C13B H13B 0.94 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.94 . ?
C16A N2A 1.39 . ?
C16A H16A 0.94 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.94 . ?
C18A H18A 0.94 . ?
C14B C18B 1.380(5) . ?
C14B C15B 1.387(5) . ?
C14B C20 1.389(6) . ?
C15B C16B 1.370(5) . ?
C15B H15B 0.94 . ?
C16B N2B 1.293(4) . ?
C16B H16B 0.94 . ?
N2B C17B 1.295(4) . ?
C17B C18B 1.364(4) . ?
C17B H17B 0.94 . ?
C18B H18B 0.94 . ?
C19 C20 1.183(8) . ?

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 . . ?
C7 N1 C11 116.91(9) . . ?
O1 C1 C2 121.88(8) . . ?
O1 C1 C6 118.23(9) . . ?
C2 C1 C6 119.89(9) . . ?
C1 C2 C3 120.42(8) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.20(8) . . ?
O2 C3 C4 117.94(9) . . ?
C2 C3 C4 119.86(10) . . ?
C5 C4 C3 118.84(10) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.94(9) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.04(10) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.28(10) . . ?
N1 C7 H7 118.4 . . ?
C8 C7 H7 118.4 . . ?
C7 C8 C9 119.60(9) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C19 C9 C8 126.5(3) . . ?
C19 C9 C10 116.1(3) . . ?
C8 C9 C10 117.38(9) . . ?
C19 C9 C12B 15.7(5) . . ?
C8 C9 C12B 142.0(6) . . ?
C10 C9 C12B 100.5(5) . . ?
C8 C9 C12A 113.6(2) . . ?
C10 C9 C12A 128.9(2) . . ?
C11 C10 C9 119.00(10) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N1 C11 C10 123.79(10) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13A C12A C9 121.3(4) . . ?
C13A C12A H12A 119.3 . . ?
C9 C12A H12A 119.3 . . ?
C12A C13A C14A 125.6(4) . . ?
C12A C13A H13A 117.2 . . ?
C14A C13A H13A 117.2 . . ?
C13B C12B C9 128.8(14) . . ?
C13B C12B H12B 115.6 . . ?
C9 C12B H12B 115.6 . . ?
C12B C13B C14B 130.0(13) . . ?
C12B C13B H13B 115 . . ?
C14B C13B H13B 115 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13A 121.1(3) . . ?
C18A C14A C13A 118.9(3) . . ?
C14A C15A C16A 120 . . ?
C14A C15A H15A 120 . . ?
C16A C15A H15A 120 . . ?
N2A C16A C15A 120 . . ?
N2A C16A H16A 120 . . ?
C15A C16A H16A 120 . . ?
C16A N2A C17A 120 . . ?
C18A C17A N2A 120 . . ?
C18A C17A H17A 120 . . ?
N2A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C15B 114.8(3) . . ?
C18B C14B C20 119.8(4) . . ?
C15B C14B C20 125.4(4) . . ?
C18B C14B C13B 134.4(8) . . ?
C15B C14B C13B 110.4(7) . . ?
C20 C14B C13B 15.5(5) . . ?
C16B C15B C14B 119.3(3) . . ?
C16B C15B H15B 120.3 . . ?
C14B C15B H15B 120.3 . . ?
N2B C16B C15B 126.5(3) . . ?
N2B C16B H16B 116.8 . . ?
C15B C16B H16B 116.8 . . ?
C16B N2B C17B 113.0(3) . . ?
N2B C17B C18B 127.8(4) . . ?
N2B C17B H17B 116.1 . . ?
C18B C17B H17B 116.1 . . ?
C17B C18B C14B 118.6(3) . . ?
C17B C18B H18B 120.7 . . ?
C14B C18B H18B 120.7 . . ?
C20 C19 C9 175.5(9) . . ?
C19 C20 C14B 177.6(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 1.92 2.7497(11) 175.2 1_556 yes
O2 H2A N2A^a 0.83 1.98 2.81(3) 176.3 2_666 yes
O2 H2A N2B^b 0.83 1.88 2.712(5) 177.4 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_BE50_BA50_290
_database_code_depnum_ccdc_archive 'CCDC 1995698'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT911_BE50_BA50_290       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         12 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2020-04-01T17:49:39-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C18 H15.02 N2 O2'
_chemical_formula_weight         291.34

#----------------------------------------------------------------------------#
#                   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                   8.20840(10)
_cell_length_b                   9.88002(10)
_cell_length_c                   10.94248(10)
_cell_angle_alpha                92.8140(8)
_cell_angle_beta                 107.7114(9)
_cell_angle_gamma                114.3110(11)
_cell_volume                     754.704(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    15728
_cell_measurement_theta_min      4.315
_cell_measurement_theta_max      76.62

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

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.088
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             307
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 2 0.1024
4 1 0 0.0468
5 -1 -3 0.0658
-4 -1 0 0.0438
-1 5 -4 0.0508
5 -3 0 0.0435
1 -6 4 0.0337
-2 -4 4 0.0464
-2 2 -6 0.081
-5 1 -1 0.0444
-4 2 -4 0.0582
-1 -5 -1 0.0561
-4 -2 1 0.0435
-2 6 2 0.0954
1 5 1 0.0835
4 -6 1 0.0427
0 -6 2 0.0367
-2 -5 3 0.0426
3 4 -3 0.0582
-1 -1 7 0.0957
-5 0 4 0.0804
-1 6 0 0.0733
-2 4 -5 0.054
4 2 -4 0.0654

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

_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.72773
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.956

#----------------------------------------------------------------------------#
#                   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      0.0607917
_diffrn_orient_matrix_ub_12      0.0567316
_diffrn_orient_matrix_ub_13      0.1479539
_diffrn_orient_matrix_ub_21      -0.0027264
_diffrn_orient_matrix_ub_22      -0.1526027
_diffrn_orient_matrix_ub_23      0.0260577
_diffrn_orient_matrix_ub_31      0.2118541
_diffrn_orient_matrix_ub_32      0.063239
_diffrn_orient_matrix_ub_33      0.013828
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_number            28018
_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         4.33
_diffrn_reflns_theta_max         77.365
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.961
_reflns_Friedel_coverage         0
_reflns_number_total             3093
_reflns_number_gt                2700
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_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)+(0.0537P)²+0.0521P] 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(8)
_refine_ls_number_reflns         3093
_refine_ls_number_parameters     284
_refine_ls_number_restraints     567
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.104
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.027

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


_refine_special_details          
;
 To help model the substitution of the bis(4-pyridyl)acetylene with 
 1,2-bis(4-pyridyl)ethylene, the atom sites N2 and  C12 < C18, were split into
 parts A and B. The site associated with the rings were allowed to free refine
 their site occupancies to a total value of 1.0, while the C12 and C13 sites 
 were constrained to 0.51 and C19 and C20 (acetyl moiety) were constrained to
 0.49. To help maintain reasonable ADP and bond lengths, SIMU, RIGU, and DFIX 
 restraints and constraints were applied. At this temperature the ratio of the
 disordered BPE sites (A and B) were 0.43 and 0.08, 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 0.16880(11) 0.14728(9) 0.30452(7) 0.0637(2) Uani 1 1 d . . . . .
H1 H 0.200759 0.172447 0.383946 0.096 Uiso 1 1 calc R U . . .
O2 O 0.81696(12) 0.22000(11) 0.43143(8) 0.0728(3) Uani 1 1 d . . . . .
H2A H 0.821696 0.255832 0.502353 0.109 Uiso 1 1 calc R U . . .
N1 N 0.26190(14) 0.24234(12) -0.43205(9) 0.0634(3) Uani 1 1 d . . . . .
C1 C 0.31866(15) 0.14701(10) 0.27597(9) 0.0509(2) Uani 1 1 d . . . . .
C2 C 0.49256(15) 0.18236(11) 0.37256(9) 0.0512(2) Uani 1 1 d . . . . .
H2 H 0.508598 0.206223 0.460044 0.061 Uiso 1 1 calc R U . . .
C3 C 0.64338(16) 0.18251(11) 0.33998(10) 0.0549(3) Uani 1 1 d . . . . .
C4 C 0.61813(19) 0.14393(13) 0.20914(11) 0.0643(3) Uani 1 1 d . . . . .
H4 H 0.717494 0.142135 0.186175 0.077 Uiso 1 1 calc R U . . .
C5 C 0.4441(2) 0.10854(13) 0.11448(11) 0.0683(3) Uani 1 1 d . . . . .
H5 H 0.427313 0.083237 0.027032 0.082 Uiso 1 1 calc R U . . .
C6 C 0.29362(18) 0.10946(12) 0.14545(10) 0.0623(3) Uani 1 1 d . . . . .
H6 H 0.177097 0.085255 0.079794 0.075 Uiso 1 1 calc R U . . .
C7 C 0.19715(17) 0.14807(13) -0.35656(11) 0.0626(3) Uani 1 1 d . . . . .
H7 H 0.1546 0.045038 -0.384952 0.075 Uiso 1 1 calc R U . . .
C8 C 0.18974(16) 0.19457(13) -0.23916(11) 0.0597(3) Uani 1 1 d . . . . .
H8 H 0.142573 0.124041 -0.190088 0.072 Uiso 1 1 calc R U . . .
C9 C 0.25309(15) 0.34753(12) -0.19409(10) 0.0542(3) Uani 1 1 d D U . . .
C10 C 0.32594(17) 0.44695(13) -0.27024(12) 0.0628(3) Uani 1 1 d . . . . .
H10 H 0.374291 0.55091 -0.242536 0.075 Uiso 1 1 calc R U . . .
C11 C 0.32576(17) 0.39001(14) -0.38693(12) 0.0660(3) Uani 1 1 d . . . . .
H11 H 0.372818 0.458016 -0.43783 0.079 Uiso 1 1 calc R U . . .
C12A C 0.2197(15) 0.3789(7) -0.0669(8) 0.0475(11) Uani 0.432(3) 1 d D U P A 1
H12A H 0.16607 0.298266 -0.028219 0.057 Uiso 0.432(3) 1 calc R U P A 1
C13A C 0.2655(5) 0.5178(4) -0.0113(4) 0.0444(7) Uani 0.432(3) 1 d D U P A 1
H13A H 0.323932 0.596165 -0.050491 0.053 Uiso 0.432(3) 1 calc R U P A 1
C12B C 0.272(5) 0.4555(14) -0.083(3) 0.055(3) Uani 0.078(3) 1 d D U P A 2
H12B H 0.343427 0.558371 -0.078652 0.066 Uiso 0.078(3) 1 calc R U P A 2
C13B C 0.199(4) 0.4190(14) 0.007(2) 0.054(3) Uani 0.078(3) 1 d D U P A 2
H13B H 0.127459 0.315875 0.001313 0.064 Uiso 0.078(3) 1 calc R U P A 2
C14A C 0.2317(14) 0.5611(7) 0.1099(7) 0.0431(12) Uani 0.432(3) 1 d DG U P A 1
C15A C 0.1502(14) 0.4526(7) 0.1774(8) 0.0514(14) Uani 0.432(3) 1 d G U P A 1
H15A H 0.11564 0.3512 0.148413 0.062 Uiso 0.432(3) 1 calc R U P A 1
C16A C 0.1202(15) 0.4956(9) 0.2884(8) 0.0526(16) Uani 0.432(3) 1 d G U P A 1
H16A H 0.065589 0.422996 0.333572 0.063 Uiso 0.432(3) 1 calc R U P A 1
N2A N 0.1718(15) 0.6471(10) 0.3318(7) 0.0509(17) Uani 0.432(3) 1 d G U P A 1
C17A C 0.2533(15) 0.7557(8) 0.2642(8) 0.0527(14) Uani 0.432(3) 1 d G U P A 1
H17A H 0.287843 0.857042 0.293244 0.063 Uiso 0.432(3) 1 calc R U P A 1
C18A C 0.2833(14) 0.7126(7) 0.1533(7) 0.0518(13) Uani 0.432(3) 1 d G U P A 1
H18A H 0.337896 0.785248 0.108085 0.062 Uiso 0.432(3) 1 calc R U P A 1
C14B C 0.2144(11) 0.5245(6) 0.1209(6) 0.0544(13) Uani 0.568(3) 1 d D U P A 2
C15B C 0.1284(12) 0.4427(7) 0.2017(7) 0.0598(11) Uani 0.568(3) 1 d . U P A 2
H15B H 0.080018 0.3377 0.186598 0.072 Uiso 0.568(3) 1 calc R U P A 2
C16B C 0.1150(12) 0.5174(8) 0.3042(7) 0.0582(11) Uani 0.568(3) 1 d . U P A 2
H16B H 0.055209 0.458277 0.355667 0.07 Uiso 0.568(3) 1 calc R U P A 2
N2B N 0.1775(13) 0.6622(9) 0.3362(6) 0.0636(15) Uani 0.568(3) 1 d . U P A 2
C17B C 0.2585(13) 0.7365(7) 0.2594(8) 0.0655(14) Uani 0.568(3) 1 d . U P A 2
H17B H 0.308036 0.841419 0.279622 0.079 Uiso 0.568(3) 1 calc R U P A 2
C18B C 0.2796(10) 0.6789(6) 0.1530(6) 0.0579(11) Uani 0.568(3) 1 d . U P A 2
H18B H 0.336879 0.742469 0.102861 0.069 Uiso 0.568(3) 1 calc R U P A 2
C19 C 0.2487(13) 0.4113(8) -0.0794(7) 0.0617(16) Uani 0.49 1 d D U P A 2
C20 C 0.2362(7) 0.4638(6) 0.0132(4) 0.0649(10) Uani 0.49 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   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(13) . ?
O1 H1 0.82 . ?
O2 C3 1.3528(14) . ?
O2 H2A 0.82 . ?
N1 C7 1.3294(15) . ?
N1 C11 1.3376(15) . ?
C1 C2 1.3827(15) . ?
C1 C6 1.3880(14) . ?
C2 C3 1.3881(15) . ?
C2 H2 0.93 . ?
C3 C4 1.3925(14) . ?
C4 C5 1.3741(18) . ?
C4 H4 0.93 . ?
C5 C6 1.3802(17) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.3703(15) . ?
C7 H7 0.93 . ?
C8 C9 1.3860(15) . ?
C8 H8 0.93 . ?
C9 C10 1.3845(16) . ?
C9 C19 1.394(8) . ?
C9 C12B 1.502(16) . ?
C9 C12A 1.539(7) . ?
C10 C11 1.3691(16) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12A C13A 1.323(8) . ?
C12A H12A 0.93 . ?
C13A C14A 1.512(6) . ?
C13A H13A 0.93 . ?
C12B C13B 1.299(18) . ?
C12B H12B 0.93 . ?
C13B C14B 1.522(16) . ?
C13B H13B 0.93 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.93 . ?
C16A N2A 1.39 . ?
C16A H16A 0.93 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.93 . ?
C18A H18A 0.93 . ?
C14B C18B 1.378(5) . ?
C14B C15B 1.384(5) . ?
C14B C20 1.388(6) . ?
C15B C16B 1.369(5) . ?
C15B H15B 0.93 . ?
C16B N2B 1.292(4) . ?
C16B H16B 0.93 . ?
N2B C17B 1.298(4) . ?
C17B C18B 1.360(4) . ?
C17B H17B 0.93 . ?
C18B H18B 0.93 . ?
C19 C20 1.167(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C7 N1 C11 116.66(9) . . ?
O1 C1 C2 121.98(9) . . ?
O1 C1 C6 118.19(10) . . ?
C2 C1 C6 119.83(10) . . ?
C1 C2 C3 120.52(9) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O2 C3 C2 122.25(9) . . ?
O2 C3 C4 118.04(10) . . ?
C2 C3 C4 119.70(10) . . ?
C5 C4 C3 118.98(11) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.89(10) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.05(11) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.52(10) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 119.50(10) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 117.38(10) . . ?
C10 C9 C19 116.5(3) . . ?
C8 C9 C19 126.1(3) . . ?
C10 C9 C12B 100.8(5) . . ?
C8 C9 C12B 141.8(5) . . ?
C19 C9 C12B 15.7(4) . . ?
C10 C9 C12A 129.7(3) . . ?
C8 C9 C12A 112.8(2) . . ?
C11 C10 C9 119.03(11) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N1 C11 C10 123.88(11) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13A C12A C9 121.5(4) . . ?
C13A C12A H12A 119.2 . . ?
C9 C12A H12A 119.2 . . ?
C12A C13A C14A 126.1(4) . . ?
C12A C13A H13A 117 . . ?
C14A C13A H13A 117 . . ?
C13B C12B C9 126.2(12) . . ?
C13B C12B H12B 116.9 . . ?
C9 C12B H12B 116.9 . . ?
C12B C13B C14B 127.9(11) . . ?
C12B C13B H13B 116 . . ?
C14B C13B H13B 116 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13A 121.2(4) . . ?
C18A C14A C13A 118.8(4) . . ?
C16A C15A C14A 120 . . ?
C16A C15A H15A 120 . . ?
C14A C15A H15A 120 . . ?
C15A C16A N2A 120 . . ?
C15A C16A H16A 120 . . ?
N2A C16A H16A 120 . . ?
C17A N2A C16A 120 . . ?
N2A C17A C18A 120 . . ?
N2A C17A H17A 120 . . ?
C18A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C15B 114.8(3) . . ?
C18B C14B C20 119.5(5) . . ?
C15B C14B C20 125.7(4) . . ?
C18B C14B C13B 134.0(7) . . ?
C15B C14B C13B 110.9(6) . . ?
C20 C14B C13B 15.3(5) . . ?
C16B C15B C14B 119.5(3) . . ?
C16B C15B H15B 120.2 . . ?
C14B C15B H15B 120.2 . . ?
N2B C16B C15B 126.3(3) . . ?
N2B C16B H16B 116.8 . . ?
C15B C16B H16B 116.8 . . ?
C16B N2B C17B 113.0(3) . . ?
N2B C17B C18B 127.6(4) . . ?
N2B C17B H17B 116.2 . . ?
C18B C17B H17B 116.2 . . ?
C17B C18B C14B 118.7(3) . . ?
C17B C18B H18B 120.6 . . ?
C14B C18B H18B 120.6 . . ?
C20 C19 C9 176.7(9) . . ?
C19 C20 C14B 177.9(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 0.82 1.94 2.7529(12) 174.6 1_556 yes
O2 H2A N2A^a 0.82 1.99 2.80(4) 176.1 2_666 yes
O2 H2A N2B^b 0.82 1.9 2.723(5) 177.7 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_BE75_BA25_190
_database_code_depnum_ccdc_archive 'CCDC 1995699'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT041_BE75_BA25_190       
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check 
RESPONSE: Due to a rounding error in the shelx program.
;
_vrf_PLAT155_BE75_BA25_190       
;
PROBLEM: The Triclinic Unitcell is NOT Reduced ..........     Please Do !  
RESPONSE: The unit cell was not reduced to maintain continuity throughout 
          the structures and temperatures. 
;
_vrf_PLAT911_BE75_BA25_190       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2020-04-01T11:35:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C18.01 H15.51 N2 O2'
_chemical_formula_weight         291.92

#----------------------------------------------------------------------------#
#                   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                   8.09764(12)
_cell_length_b                   9.86690(19)
_cell_length_c                   10.89543(13)
_cell_angle_alpha                92.5280(17)
_cell_angle_beta                 107.5880(12)
_cell_angle_gamma                114.4693(14)
_cell_volume                     740.79(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    19321
_cell_measurement_theta_min      4.326
_cell_measurement_theta_max      77.102

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

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.066
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             307
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 4 0 0.0556
-1 4 4 0.0717
5 4 1 0.0337
-2 -4 3 0.0581
2 5 -2 0.0622
-5 -3 -4 0.0659
-2 -5 2 0.0477
-2 0 5 0.0662
-5 -4 -1 0.0318
-1 -2 -7 0.0688
1 -4 -5 0.0636
-5 0 0 0.0498
2 -4 0 0.0503
3 3 -4 0.0609
0 3 6 0.0788
-2 -6 -1 0.0374
4 0 -2 0.0542
1 -4 3 0.0598

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

_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.90939
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.887
_shelx_estimated_absorpt_T_max   0.955

#----------------------------------------------------------------------------#
#                   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      -0.0955558
_diffrn_orient_matrix_ub_12      0.1047296
_diffrn_orient_matrix_ub_13      -0.1136007
_diffrn_orient_matrix_ub_21      0.144325
_diffrn_orient_matrix_ub_22      0.0786799
_diffrn_orient_matrix_ub_23      -0.0453694
_diffrn_orient_matrix_ub_31      0.1242606
_diffrn_orient_matrix_ub_32      -0.1158965
_diffrn_orient_matrix_ub_33      -0.0889297
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_number            27916
_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       13
_diffrn_reflns_theta_min         4.34
_diffrn_reflns_theta_max         77.292
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_reflns_Friedel_coverage         0
_reflns_number_total             3058
_reflns_number_gt                2829
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_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)+(0.0500P)²+0.0960P] 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(7)
_refine_ls_number_reflns         3058
_refine_ls_number_parameters     284
_refine_ls_number_restraints     579
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.031

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

_refine_special_details          
;
 To help model the substitution of the bis(4-pyridyl)acetylene with 
 1,2-bis(4-pyridyl)ethylene, the atom sites N2 and  C12 < C18, were split into
 parts A and B. The site associated with the rings were allowed to free refine
 their site occupancies to a total value of 1.0, while the C12 and C13 sites 
 were constrained to 0.75 and C19 and C20 (acetyl moiety) were constrained to
 0.25. To help maintain reasonable ADP and bond lengths, SIMU, RIGU, and DFIX 
 restraints and constraints were applied. At this temperature the ratio of the
 disordered BPE sites (A and B) were 0.71 and 0.04, 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 0.16626(10) 0.15442(8) 0.30497(6) 0.03834(18) Uani 1 1 d . . . . .
H1 H 0.19917 0.179755 0.38655 0.058 Uiso 1 1 calc R U . . .
O2 O 0.82352(10) 0.22603(9) 0.43239(7) 0.0440(2) Uani 1 1 d . . . . .
H2A H 0.828209 0.26322 0.504933 0.066 Uiso 1 1 calc R U . . .
N1 N 0.26228(12) 0.24569(10) -0.43144(8) 0.0393(2) Uani 1 1 d . . . . .
C1 C 0.31706(13) 0.15188(9) 0.27634(9) 0.0316(2) Uani 1 1 d . . . . .
C2 C 0.49449(13) 0.18925(10) 0.37346(8) 0.0320(2) Uani 1 1 d . . . . .
H2 H 0.511942 0.216349 0.462846 0.038 Uiso 1 1 calc R U . . .
C3 C 0.64717(14) 0.18726(10) 0.34067(9) 0.0339(2) Uani 1 1 d . . . . .
C4 C 0.62070(15) 0.14481(11) 0.20941(9) 0.0391(2) Uani 1 1 d . . . . .
H4 H 0.723257 0.141848 0.186047 0.047 Uiso 1 1 calc R U . . .
C5 C 0.44273(16) 0.10723(11) 0.11421(9) 0.0409(2) Uani 1 1 d . . . . .
H5 H 0.424408 0.078682 0.024887 0.049 Uiso 1 1 calc R U . . .
C6 C 0.29013(15) 0.10999(11) 0.14536(9) 0.0376(2) Uani 1 1 d . . . . .
H6 H 0.168981 0.083704 0.07833 0.045 Uiso 1 1 calc R U . . .
C7 C 0.19672(14) 0.14664(12) -0.35767(10) 0.0390(2) Uani 1 1 d . . . . .
H7 H 0.155513 0.042211 -0.388423 0.047 Uiso 1 1 calc R U . . .
C8 C 0.18578(14) 0.18851(11) -0.23861(9) 0.0365(2) Uani 1 1 d . . . . .
H8 H 0.136779 0.113648 -0.189985 0.044 Uiso 1 1 calc R U . . .
C9 C 0.24692(13) 0.34081(11) -0.19044(9) 0.0328(2) Uani 1 1 d D U . . .
C10 C 0.32135(14) 0.44492(11) -0.26515(10) 0.0380(2) Uani 1 1 d . . . . .
H10 H 0.369369 0.550564 -0.234989 0.046 Uiso 1 1 calc R U . . .
C11 C 0.32443(14) 0.39259(12) -0.38358(10) 0.0401(2) Uani 1 1 d . . . . .
H11 H 0.373446 0.4649 -0.43416 0.048 Uiso 1 1 calc R U . . .
C12A C 0.2178(8) 0.3774(4) -0.0656(4) 0.0290(6) Uani 0.715(7) 1 d D U P A 1
H12A H 0.162136 0.296767 -0.02373 0.035 Uiso 0.715(7) 1 calc R U P A 1
C13A C 0.2676(4) 0.5199(3) -0.0109(2) 0.0274(5) Uani 0.715(7) 1 d D U P A 1
H13A H 0.32798 0.599711 -0.051943 0.033 Uiso 0.715(7) 1 calc R U P A 1
C12B C 0.272(7) 0.437(3) -0.081(4) 0.031(4) Uani 0.039(7) 1 d D U P A 2
H12B H 0.369723 0.535076 -0.074815 0.037 Uiso 0.039(7) 1 calc R U P A 2
C13B C 0.212(7) 0.440(3) 0.012(4) 0.035(4) Uani 0.039(7) 1 d D U P A 2
H13B H 0.127678 0.337784 0.011615 0.042 Uiso 0.039(7) 1 calc R U P A 2
C14A C 0.2343(8) 0.5616(4) 0.1105(4) 0.0278(7) Uani 0.715(7) 1 d DG U P A 1
C15A C 0.1487(8) 0.4535(3) 0.1784(4) 0.0316(7) Uani 0.715(7) 1 d G U P A 1
H15A H 0.11131 0.349484 0.149202 0.038 Uiso 0.715(7) 1 calc R U P A 1
C16A C 0.1177(8) 0.4977(3) 0.2890(4) 0.0319(8) Uani 0.715(7) 1 d G U P A 1
H16A H 0.059204 0.423905 0.335403 0.038 Uiso 0.715(7) 1 calc R U P A 1
N2A N 0.1724(9) 0.6500(4) 0.3317(4) 0.0338(9) Uani 0.715(7) 1 d G U P A 1
C17A C 0.2580(8) 0.7580(3) 0.2638(5) 0.0317(7) Uani 0.715(7) 1 d G U P A 1
H17A H 0.295417 0.862107 0.292958 0.038 Uiso 0.715(7) 1 calc R U P A 1
C18A C 0.2890(8) 0.7138(4) 0.1532(4) 0.0311(7) Uani 0.715(7) 1 d G U P A 1
H18A H 0.347524 0.787689 0.106757 0.037 Uiso 0.715(7) 1 calc R U P A 1
C14B C 0.218(2) 0.5318(14) 0.1158(12) 0.039(2) Uani 0.285(7) 1 d D U P A 2
C15B C 0.134(2) 0.4505(10) 0.2015(12) 0.0396(19) Uani 0.285(7) 1 d . U P A 2
H15B H 0.084556 0.343209 0.188761 0.047 Uiso 0.285(7) 1 calc R U P A 2
C16B C 0.124(2) 0.5282(12) 0.3026(11) 0.0320(16) Uani 0.285(7) 1 d . U P A 2
H16B H 0.063347 0.464635 0.354764 0.038 Uiso 0.285(7) 1 calc R U P A 2
N2B N 0.176(2) 0.6610(11) 0.3404(12) 0.040(2) Uani 0.285(7) 1 d . U P A 2
C17B C 0.249(2) 0.7275(13) 0.2655(14) 0.0362(16) Uani 0.285(7) 1 d . U P A 2
H17B H 0.296831 0.834382 0.287455 0.043 Uiso 0.285(7) 1 calc R U P A 2
C18B C 0.277(2) 0.6824(13) 0.1557(12) 0.0352(17) Uani 0.285(7) 1 d . U P A 2
H18B H 0.336166 0.754681 0.108419 0.042 Uiso 0.285(7) 1 calc R U P A 2
C19 C 0.242(3) 0.4017(18) -0.0786(15) 0.040(2) Uani 0.25 1 d D U P A 2
C20 C 0.2446(17) 0.4764(18) 0.0109(10) 0.0473(18) Uani 0.25 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   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(11) . ?
O1 H1 0.84 . ?
O2 C3 1.3548(12) . ?
O2 H2A 0.84 . ?
N1 C7 1.3343(14) . ?
N1 C11 1.3404(13) . ?
C1 C2 1.3885(13) . ?
C1 C6 1.3929(13) . ?
C2 C3 1.3939(13) . ?
C2 H2 0.95 . ?
C3 C4 1.3980(13) . ?
C4 C5 1.3821(15) . ?
C4 H4 0.95 . ?
C5 C6 1.3869(15) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.3833(13) . ?
C7 H7 0.95 . ?
C8 C9 1.3914(13) . ?
C8 H8 0.95 . ?
C9 C19 1.356(12) . ?
C9 C10 1.3923(14) . ?
C9 C12B 1.397(19) . ?
C9 C12A 1.503(3) . ?
C10 C11 1.3797(14) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
C12A C13A 1.344(5) . ?
C12A H12A 0.95 . ?
C13A C14A 1.500(3) . ?
C13A H13A 0.95 . ?
C12B C13B 1.254(19) . ?
C12B H12B 0.95 . ?
C13B C14B 1.394(19) . ?
C13B H13B 0.95 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.95 . ?
C16A N2A 1.39 . ?
C16A H16A 0.95 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.95 . ?
C18A H18A 0.95 . ?
C14B C20 1.357(12) . ?
C14B C18B 1.362(9) . ?
C14B C15B 1.407(9) . ?
C15B C16B 1.355(9) . ?
C15B H15B 0.95 . ?
C16B N2B 1.206(9) . ?
C16B C17B 1.929(15) . ?
C16B H16B 0.95 . ?
N2B C17B 1.208(8) . ?
C17B C18B 1.373(7) . ?
C17B H17B 0.95 . ?
C18B H18B 0.95 . ?
C19 C20 1.183(14) . ?

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 . . ?
C7 N1 C11 116.92(8) . . ?
O1 C1 C2 121.84(8) . . ?
O1 C1 C6 118.23(8) . . ?
C2 C1 C6 119.92(9) . . ?
C1 C2 C3 120.44(8) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.14(8) . . ?
O2 C3 C4 118.01(9) . . ?
C2 C3 C4 119.86(9) . . ?
C5 C4 C3 118.84(9) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.89(8) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.04(9) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.24(9) . . ?
N1 C7 H7 118.4 . . ?
C8 C7 H7 118.4 . . ?
C7 C8 C9 119.66(9) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C19 C9 C8 127.8(7) . . ?
C19 C9 C10 115.0(7) . . ?
C8 C9 C10 117.20(9) . . ?
C19 C9 C12B 13.9(8) . . ?
C8 C9 C12B 141.2(12) . . ?
C10 C9 C12B 101.5(11) . . ?
C8 C9 C12A 116.94(17) . . ?
C10 C9 C12A 125.79(17) . . ?
C11 C10 C9 119.11(9) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C11 C10 123.82(9) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13A C12A C9 122.4(3) . . ?
C13A C12A H12A 118.8 . . ?
C9 C12A H12A 118.8 . . ?
C12A C13A C14A 124.4(3) . . ?
C12A C13A H13A 117.8 . . ?
C14A C13A H13A 117.8 . . ?
C13B C12B C9 143(3) . . ?
C13B C12B H12B 108.6 . . ?
C9 C12B H12B 108.6 . . ?
C12B C13B C14B 145(3) . . ?
C12B C13B H13B 107.3 . . ?
C14B C13B H13B 107.3 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13A 122.3(2) . . ?
C18A C14A C13A 117.7(2) . . ?
C14A C15A C16A 120 . . ?
C14A C15A H15A 120 . . ?
C16A C15A H15A 120 . . ?
N2A C16A C15A 120 . . ?
N2A C16A H16A 120 . . ?
C15A C16A H16A 120 . . ?
C16A N2A C17A 120 . . ?
C18A C17A N2A 120 . . ?
C18A C17A H17A 120 . . ?
N2A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C20 C14B C18B 123.1(11) . . ?
C20 C14B C13B 14.7(8) . . ?
C18B C14B C13B 137.3(14) . . ?
C20 C14B C15B 127.9(10) . . ?
C18B C14B C15B 109.0(5) . . ?
C13B C14B C15B 113.6(12) . . ?
C16B C15B C14B 118.7(5) . . ?
C16B C15B H15B 120.7 . . ?
C14B C15B H15B 120.7 . . ?
N2B C16B C15B 133.6(6) . . ?
N2B C16B C17B 37.0(4) . . ?
C15B C16B C17B 96.6(4) . . ?
N2B C16B H16B 113.2 . . ?
C15B C16B H16B 113.2 . . ?
C17B C16B H16B 150.2 . . ?
C16B N2B C17B 106.0(7) . . ?
N2B C17B C18B 134.0(8) . . ?
N2B C17B C16B 36.9(4) . . ?
C18B C17B C16B 97.1(5) . . ?
N2B C17B H17B 113 . . ?
C18B C17B H17B 113 . . ?
C16B C17B H17B 149.9 . . ?
C14B C18B C17B 118.6(6) . . ?
C14B C18B H18B 120.7 . . ?
C17B C18B H18B 120.7 . . ?
C20 C19 C9 169(2) . . ?
C19 C20 C14B 167(2) . . ?

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 2.7396(10) 175.6 1_556 yes
O2 H2A N2A^a 0.84 1.94 2.78(2) 177.2 2_666 yes
O2 H2A N2B^b 0.84 1.83 2.668(9) 176.9 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_BE75_BA25_210
_database_code_depnum_ccdc_archive 'CCDC 1995700'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT155_BE75_BA25_210       
;
PROBLEM: The Triclinic Unitcell is NOT Reduced ..........     Please Do !  
RESPONSE: The unit cell was not reduced to maintain continuity throughout 
          the structures and temperatures.
;
_vrf_PLAT911_BE75_BA25_210       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2020-04-01T11:36:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C18 H15.50 N2 O2'
_chemical_formula_weight         291.88

#----------------------------------------------------------------------------#
#                   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                   8.11309(11)
_cell_length_b                   9.87420(17)
_cell_length_c                   10.89995(12)
_cell_angle_alpha                92.6153(16)
_cell_angle_beta                 107.5529(11)
_cell_angle_gamma                114.4384(13)
_cell_volume                     743.20(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    18922
_cell_measurement_theta_min      4.327
_cell_measurement_theta_max      76.927

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

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.066
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             307
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 4 0 0.0556
-1 4 4 0.0717
5 4 1 0.0337
-2 -4 3 0.0581
2 5 -2 0.0622
-5 -3 -4 0.0659
-2 -5 2 0.0477
-2 0 5 0.0662
-5 -4 -1 0.0318
-1 -2 -7 0.0688
1 -4 -5 0.0636
-5 0 0 0.0498
2 -4 0 0.0503
3 3 -4 0.0609
0 3 6 0.0788
-2 -6 -1 0.0374
4 0 -2 0.0542
1 -4 3 0.0598

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

_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.8928
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.887
_shelx_estimated_absorpt_T_max   0.956

#----------------------------------------------------------------------------#
#                   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      -0.0955597
_diffrn_orient_matrix_ub_12      0.1047479
_diffrn_orient_matrix_ub_13      -0.1136285
_diffrn_orient_matrix_ub_21      0.1436057
_diffrn_orient_matrix_ub_22      0.0788873
_diffrn_orient_matrix_ub_23      -0.0450764
_diffrn_orient_matrix_ub_31      0.1244702
_diffrn_orient_matrix_ub_32      -0.115497
_diffrn_orient_matrix_ub_33      -0.088941
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_number            27914
_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       13
_diffrn_reflns_theta_min         4.339
_diffrn_reflns_theta_max         77.363
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_reflns_Friedel_coverage         0
_reflns_number_total             3070
_reflns_number_gt                2835
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_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)+(0.0507P)²+0.0876P] 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(8)
_refine_ls_number_reflns         3070
_refine_ls_number_parameters     284
_refine_ls_number_restraints     579
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.033
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0922
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.03

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

_refine_special_details          
;
 To help model the substitution of the bis(4-pyridyl)acetylene with 
 1,2-bis(4-pyridyl)ethylene, the atom sites N2 and  C12 < C18, were split into
 parts A and B. The site associated with the rings were allowed to free refine
 their site occupancies to a total value of 1.0, while the C12 and C13 sites 
 were constrained to 0.75 and C19 and C20 (acetyl moiety) were constrained to
 0.25. To help maintain reasonable ADP and bond lengths, SIMU, RIGU, and DFIX 
 restraints and constraints were applied. At this temperature the ratio of the
 disordered BPE sites (A and B) were 0.70 and 0.05, 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 0.16661(10) 0.15384(8) 0.30489(7) 0.04282(19) Uani 1 1 d . . . . .
H1 H 0.199111 0.179311 0.385437 0.064 Uiso 1 1 calc R U . . .
O2 O 0.82265(10) 0.22591(9) 0.43212(7) 0.0492(2) Uani 1 1 d . . . . .
H2A H 0.827278 0.262645 0.503818 0.074 Uiso 1 1 calc R U . . .
N1 N 0.26212(12) 0.24546(11) -0.43138(8) 0.0438(2) Uani 1 1 d . . . . .
C1 C 0.31725(14) 0.15155(10) 0.27636(9) 0.0350(2) Uani 1 1 d . . . . .
C2 C 0.49417(14) 0.18887(10) 0.37328(9) 0.0355(2) Uani 1 1 d . . . . .
H2 H 0.511355 0.215548 0.461727 0.043 Uiso 1 1 calc R U . . .
C3 C 0.64660(14) 0.18712(11) 0.34047(9) 0.0376(2) Uani 1 1 d . . . . .
C4 C 0.62028(16) 0.14484(11) 0.20925(10) 0.0434(2) Uani 1 1 d . . . . .
H4 H 0.721573 0.142021 0.186066 0.052 Uiso 1 1 calc R U . . .
C5 C 0.44281(17) 0.10728(12) 0.11429(9) 0.0456(3) Uani 1 1 d . . . . .
H5 H 0.424761 0.079204 0.02589 0.055 Uiso 1 1 calc R U . . .
C6 C 0.29064(15) 0.10975(11) 0.14546(9) 0.0418(2) Uani 1 1 d . . . . .
H6 H 0.170985 0.08358 0.079161 0.05 Uiso 1 1 calc R U . . .
C7 C 0.19667(15) 0.14684(12) -0.35762(10) 0.0434(2) Uani 1 1 d . . . . .
H7 H 0.15576 0.043504 -0.388 0.052 Uiso 1 1 calc R U . . .
C8 C 0.18602(15) 0.18907(11) -0.23872(10) 0.0408(2) Uani 1 1 d . . . . .
H8 H 0.137705 0.115235 -0.190536 0.049 Uiso 1 1 calc R U . . .
C9 C 0.24699(13) 0.34103(11) -0.19069(9) 0.0364(2) Uani 1 1 d D U . . .
C10 C 0.32118(15) 0.44476(12) -0.26546(10) 0.0422(2) Uani 1 1 d . . . . .
H10 H 0.368585 0.549261 -0.235713 0.051 Uiso 1 1 calc R U . . .
C11 C 0.32419(15) 0.39222(12) -0.38365(10) 0.0446(2) Uani 1 1 d . . . . .
H11 H 0.372633 0.463539 -0.43371 0.053 Uiso 1 1 calc R U . . .
C12A C 0.2180(8) 0.3773(4) -0.0660(4) 0.0324(6) Uani 0.705(8) 1 d D U P A 1
H12A H 0.163265 0.297515 -0.024707 0.039 Uiso 0.705(8) 1 calc R U P A 1
C13A C 0.2674(4) 0.5195(3) -0.0112(2) 0.0305(5) Uani 0.705(8) 1 d D U P A 1
H13A H 0.326203 0.598395 -0.051963 0.037 Uiso 0.705(8) 1 calc R U P A 1
C12B C 0.269(7) 0.438(3) -0.082(3) 0.036(4) Uani 0.047(8) 1 d D U P A 2
H12B H 0.356354 0.537434 -0.080624 0.043 Uiso 0.047(8) 1 calc R U P A 2
C13B C 0.214(6) 0.439(3) 0.014(3) 0.039(3) Uani 0.047(8) 1 d D U P A 2
H13B H 0.144011 0.337329 0.019331 0.047 Uiso 0.047(8) 1 calc R U P A 2
C14A C 0.2354(8) 0.5610(4) 0.1102(4) 0.0311(7) Uani 0.705(8) 1 d DG U P A 1
C15A C 0.1491(8) 0.4533(3) 0.1779(4) 0.0349(7) Uani 0.705(8) 1 d G U P A 1
H15A H 0.111754 0.350288 0.148986 0.042 Uiso 0.705(8) 1 calc R U P A 1
C16A C 0.1182(8) 0.4979(4) 0.2883(4) 0.0353(8) Uani 0.705(8) 1 d G U P A 1
H16A H 0.05985 0.425098 0.334116 0.042 Uiso 0.705(8) 1 calc R U P A 1
N2A N 0.1735(9) 0.6502(4) 0.3311(5) 0.0370(9) Uani 0.705(8) 1 d G U P A 1
C17A C 0.2597(8) 0.7579(3) 0.2634(5) 0.0361(7) Uani 0.705(8) 1 d G U P A 1
H17A H 0.297082 0.860926 0.292299 0.043 Uiso 0.705(8) 1 calc R U P A 1
C18A C 0.2907(7) 0.7133(4) 0.1529(4) 0.0337(7) Uani 0.705(8) 1 d G U P A 1
H18A H 0.348988 0.786119 0.107167 0.04 Uiso 0.705(8) 1 calc R U P A 1
C14B C 0.214(2) 0.5314(14) 0.1163(11) 0.0424(19) Uani 0.295(8) 1 d D U P A 2
C15B C 0.133(2) 0.4507(9) 0.2025(12) 0.0415(18) Uani 0.295(8) 1 d . U P A 2
H15B H 0.086235 0.34478 0.190165 0.05 Uiso 0.295(8) 1 calc R U P A 2
C16B C 0.125(2) 0.5282(13) 0.3042(11) 0.0359(16) Uani 0.295(8) 1 d . U P A 2
H16B H 0.066831 0.465254 0.356533 0.043 Uiso 0.295(8) 1 calc R U P A 2
N2B N 0.175(2) 0.6608(11) 0.3420(12) 0.044(2) Uani 0.295(8) 1 d . U P A 2
C17B C 0.245(2) 0.7267(12) 0.2668(13) 0.0391(17) Uani 0.295(8) 1 d . U P A 2
H17B H 0.293015 0.832438 0.288397 0.047 Uiso 0.295(8) 1 calc R U P A 2
C18B C 0.2714(19) 0.6809(13) 0.1565(13) 0.0431(17) Uani 0.295(8) 1 d . U P A 2
H18B H 0.328077 0.752394 0.109128 0.052 Uiso 0.295(8) 1 calc R U P A 2
C19 C 0.242(3) 0.4033(18) -0.0776(15) 0.045(3) Uani 0.25 1 d D U P A 2
C20 C 0.2445(18) 0.4766(19) 0.0109(10) 0.0516(19) Uani 0.25 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   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 1.3574(12) . ?
O1 H1 0.83 . ?
O2 C3 1.3551(12) . ?
O2 H2A 0.83 . ?
N1 C7 1.3334(14) . ?
N1 C11 1.3393(14) . ?
C1 C2 1.3871(13) . ?
C1 C6 1.3926(13) . ?
C2 C3 1.3934(13) . ?
C2 H2 0.94 . ?
C3 C4 1.3975(13) . ?
C4 C5 1.3806(16) . ?
C4 H4 0.94 . ?
C5 C6 1.3848(15) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3817(14) . ?
C7 H7 0.94 . ?
C8 C9 1.3886(14) . ?
C8 H8 0.94 . ?
C9 C19 1.372(12) . ?
C9 C10 1.3920(15) . ?
C9 C12B 1.405(19) . ?
C9 C12A 1.499(3) . ?
C10 C11 1.3776(14) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12A C13A 1.343(5) . ?
C12A H12A 0.94 . ?
C13A C14A 1.494(3) . ?
C13A H13A 0.94 . ?
C12B C13B 1.259(19) . ?
C12B H12B 0.94 . ?
C13B C14B 1.407(18) . ?
C13B H13B 0.94 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.94 . ?
C16A N2A 1.39 . ?
C16A H16A 0.94 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.94 . ?
C18A H18A 0.94 . ?
C14B C18B 1.356(9) . ?
C14B C20 1.376(12) . ?
C14B C15B 1.398(9) . ?
C15B C16B 1.355(9) . ?
C15B H15B 0.94 . ?
C16B N2B 1.208(9) . ?
C16B C17B 1.922(15) . ?
C16B H16B 0.94 . ?
N2B C17B 1.203(8) . ?
C17B C18B 1.370(7) . ?
C17B H17B 0.94 . ?
C18B H18B 0.94 . ?
C19 C20 1.169(14) . ?

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 . . ?
C7 N1 C11 116.90(8) . . ?
O1 C1 C2 121.94(8) . . ?
O1 C1 C6 118.23(9) . . ?
C2 C1 C6 119.83(9) . . ?
C1 C2 C3 120.47(8) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.16(8) . . ?
O2 C3 C4 117.99(9) . . ?
C2 C3 C4 119.85(9) . . ?
C5 C4 C3 118.81(9) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.92(9) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.10(9) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N1 C7 C8 123.23(10) . . ?
N1 C7 H7 118.4 . . ?
C8 C7 H7 118.4 . . ?
C7 C8 C9 119.73(10) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C19 C9 C8 127.9(7) . . ?
C19 C9 C10 114.9(7) . . ?
C8 C9 C10 117.17(9) . . ?
C19 C9 C12B 13.9(8) . . ?
C8 C9 C12B 141.5(10) . . ?
C10 C9 C12B 101.3(10) . . ?
C8 C9 C12A 116.76(17) . . ?
C10 C9 C12A 126.00(17) . . ?
C11 C10 C9 119.11(9) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C11 C10 123.83(10) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13A C12A C9 122.4(3) . . ?
C13A C12A H12A 118.8 . . ?
C9 C12A H12A 118.8 . . ?
C12A C13A C14A 124.5(3) . . ?
C12A C13A H13A 117.8 . . ?
C14A C13A H13A 117.8 . . ?
C13B C12B C9 142(3) . . ?
C13B C12B H12B 108.8 . . ?
C9 C12B H12B 108.8 . . ?
C12B C13B C14B 145(3) . . ?
C12B C13B H13B 107.5 . . ?
C14B C13B H13B 107.5 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13A 122.5(2) . . ?
C18A C14A C13A 117.5(2) . . ?
C14A C15A C16A 120 . . ?
C14A C15A H15A 120 . . ?
C16A C15A H15A 120 . . ?
N2A C16A C15A 120 . . ?
N2A C16A H16A 120 . . ?
C15A C16A H16A 120 . . ?
C16A N2A C17A 120 . . ?
C18A C17A N2A 120 . . ?
C18A C17A H17A 120 . . ?
N2A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C20 123.1(11) . . ?
C18B C14B C15B 108.7(6) . . ?
C20 C14B C15B 128.2(9) . . ?
C18B C14B C13B 137.7(13) . . ?
C20 C14B C13B 14.9(8) . . ?
C15B C14B C13B 113.6(12) . . ?
C16B C15B C14B 118.7(5) . . ?
C16B C15B H15B 120.6 . . ?
C14B C15B H15B 120.6 . . ?
N2B C16B C15B 133.8(7) . . ?
N2B C16B C17B 37.1(4) . . ?
C15B C16B C17B 96.7(4) . . ?
N2B C16B H16B 113.1 . . ?
C15B C16B H16B 113.1 . . ?
C17B C16B H16B 150.2 . . ?
C17B N2B C16B 105.7(7) . . ?
N2B C17B C18B 133.9(8) . . ?
N2B C17B C16B 37.2(4) . . ?
C18B C17B C16B 96.6(5) . . ?
N2B C17B H17B 113.1 . . ?
C18B C17B H17B 113.1 . . ?
C16B C17B H17B 150.3 . . ?
C14B C18B C17B 119.3(6) . . ?
C14B C18B H18B 120.4 . . ?
C17B C18B H18B 120.4 . . ?
C20 C19 C9 170(2) . . ?
C19 C20 C14B 167(2) . . ?

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 1.91 2.7425(11) 175.8 1_556 yes
O2 H2A N2A^a 0.83 1.96 2.79(2) 177.3 2_666 yes
O2 H2A N2B^b 0.83 1.82 2.648(9) 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_BE75_BA25_250
_database_code_depnum_ccdc_archive 'CCDC 1995702'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT155_BE75_BA25_250       
;
PROBLEM: The Triclinic Unitcell is NOT Reduced ..........     Please Do !  
RESPONSE: The unit cell was not reduced to maintain continuity throughout 
          the structures and temperatures.
;
# end Validation Reply Form

_audit_creation_date             2020-04-01T11:37:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C18.01 H15.51 N2 O2'
_chemical_formula_weight         292.02

#----------------------------------------------------------------------------#
#                   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                   8.14797(10)
_cell_length_b                   9.89332(16)
_cell_length_c                   10.90921(11)
_cell_angle_alpha                92.7875(14)
_cell_angle_beta                 107.4969(10)
_cell_angle_gamma                114.3638(12)
_cell_volume                     748.778(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    17759
_cell_measurement_theta_min      4.317
_cell_measurement_theta_max      76.888

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

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.066
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             307
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 4 0 0.0556
1 -4 3 0.0598
-2 -6 -1 0.0374
0 3 6 0.0788
3 3 -4 0.0609
-5 0 0 0.0498
1 -4 -5 0.0636
-1 -2 -7 0.0688
-2 0 5 0.0662
-2 -5 2 0.0477
-5 -3 -4 0.0659
2 5 -2 0.0622
-2 -4 3 0.0581
-5 -4 -1 0.0318
5 4 1 0.0337
-1 4 4 0.0717
4 0 -2 0.0542
2 -4 0 0.0503

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

_exptl_absorpt_coefficient_mu    0.69
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.92433
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.888
_shelx_estimated_absorpt_T_max   0.956

#----------------------------------------------------------------------------#
#                   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      -0.0955067
_diffrn_orient_matrix_ub_12      0.104859
_diffrn_orient_matrix_ub_13      -0.1137096
_diffrn_orient_matrix_ub_21      0.1431085
_diffrn_orient_matrix_ub_22      0.0783444
_diffrn_orient_matrix_ub_23      -0.0451432
_diffrn_orient_matrix_ub_31      0.1237935
_diffrn_orient_matrix_ub_32      -0.1152899
_diffrn_orient_matrix_ub_33      -0.0886507
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_number            28413
_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       13
_diffrn_reflns_theta_min         4.336
_diffrn_reflns_theta_max         77.205
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.973
_reflns_Friedel_coverage         0
_reflns_number_total             3097
_reflns_number_gt                2797
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_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)+(0.0534P)²+0.0690P] 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(8)
_refine_ls_number_reflns         3097
_refine_ls_number_parameters     284
_refine_ls_number_restraints     579
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.099
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.03

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

_refine_special_details          
;
 To help model the substitution of the bis(4-pyridyl)acetylene with 
 1,2-bis(4-pyridyl)ethylene, the atom sites N2 and  C12 < C18, were split into
 parts A and B. The site associated with the rings were allowed to free refine
 their site occupancies to a total value of 1.0, while the C12 and C13 sites 
 were constrained to 0.75 and C19 and C20 (acetyl moiety) were constrained to
 0.25. To help maintain reasonable ADP and bond lengths, SIMU, RIGU, and DFIX 
 restraints and constraints were applied. At this temperature the ratio of the
 disordered BPE sites (A and B) were 0.68 and 0.07, 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 0.16753(10) 0.15235(9) 0.30481(7) 0.0520(2) Uani 1 1 d . . . . .
H1 H 0.200052 0.17829 0.38528 0.078 Uiso 1 1 calc R U . . .
O2 O 0.82063(11) 0.22554(10) 0.43138(7) 0.0597(2) Uani 1 1 d . . . . .
H2A H 0.82493 0.26145 0.50329 0.09 Uiso 1 1 calc R U . . .
N1 N 0.26179(13) 0.24477(11) -0.43144(8) 0.0524(2) Uani 1 1 d . . . . .
C1 C 0.31771(14) 0.15045(10) 0.27619(9) 0.0422(2) Uani 1 1 d . . . . .
C2 C 0.49376(14) 0.18790(10) 0.37290(9) 0.0426(2) Uani 1 1 d . . . . .
H2 H 0.510764 0.214404 0.461327 0.051 Uiso 1 1 calc R U . . .
C3 C 0.64544(15) 0.18655(11) 0.34009(9) 0.0451(2) Uani 1 1 d . . . . .
C4 C 0.61948(17) 0.14469(12) 0.20904(10) 0.0522(3) Uani 1 1 d . . . . .
H4 H 0.720444 0.142106 0.185815 0.063 Uiso 1 1 calc R U . . .
C5 C 0.44316(18) 0.10720(12) 0.11429(10) 0.0546(3) Uani 1 1 d . . . . .
H5 H 0.425462 0.079524 0.025901 0.066 Uiso 1 1 calc R U . . .
C6 C 0.29144(16) 0.10909(11) 0.14542(10) 0.0501(3) Uani 1 1 d . . . . .
H6 H 0.172332 0.082801 0.079164 0.06 Uiso 1 1 calc R U . . .
C7 C 0.19672(16) 0.14748(13) -0.35739(10) 0.0522(3) Uani 1 1 d . . . . .
H7 H 0.155537 0.044152 -0.387516 0.063 Uiso 1 1 calc R U . . .
C8 C 0.18661(15) 0.19042(12) -0.23890(10) 0.0496(2) Uani 1 1 d . . . . .
H8 H 0.138653 0.117193 -0.190528 0.059 Uiso 1 1 calc R U . . .
C9 C 0.24743(14) 0.34202(12) -0.19126(9) 0.0443(2) Uani 1 1 d D U . . .
C10 C 0.32108(16) 0.44453(12) -0.26611(11) 0.0510(3) Uani 1 1 d . . . . .
H10 H 0.368438 0.548936 -0.236583 0.061 Uiso 1 1 calc R U . . .
C11 C 0.32386(16) 0.39140(13) -0.38399(11) 0.0539(3) Uani 1 1 d . . . . .
H11 H 0.372149 0.462159 -0.434134 0.065 Uiso 1 1 calc R U . . .
C12A C 0.2174(7) 0.3775(4) -0.0668(4) 0.0391(6) Uani 0.685(7) 1 d D U P A 1
H12A H 0.161752 0.297492 -0.026492 0.047 Uiso 0.685(7) 1 calc R U P A 1
C13A C 0.2667(4) 0.5189(3) -0.0110(2) 0.0376(5) Uani 0.685(7) 1 d D U P A 1
H13A H 0.325928 0.597684 -0.051295 0.045 Uiso 0.685(7) 1 calc R U P A 1
C12B C 0.271(5) 0.449(2) -0.084(2) 0.045(3) Uani 0.072(7) 1 d D U P A 2
H12B H 0.347862 0.550482 -0.082342 0.054 Uiso 0.072(7) 1 calc R U P A 2
C13B C 0.204(3) 0.428(2) 0.009(2) 0.047(3) Uani 0.072(7) 1 d D U P A 2
H13B H 0.132919 0.324617 0.007732 0.056 Uiso 0.072(7) 1 calc R U P A 2
C14A C 0.2349(8) 0.5612(4) 0.1106(4) 0.0372(8) Uani 0.685(7) 1 d DG U P A 1
C15A C 0.1495(8) 0.4535(3) 0.1780(4) 0.0421(8) Uani 0.685(7) 1 d G U P A 1
H15A H 0.112753 0.350838 0.148834 0.051 Uiso 0.685(7) 1 calc R U P A 1
C16A C 0.1185(8) 0.4977(4) 0.2885(4) 0.0427(8) Uani 0.685(7) 1 d G U P A 1
H16A H 0.060782 0.424899 0.334126 0.051 Uiso 0.685(7) 1 calc R U P A 1
N2A N 0.1729(8) 0.6496(4) 0.3317(4) 0.0446(10) Uani 0.685(7) 1 d G U P A 1
C17A C 0.2583(8) 0.7573(3) 0.2643(5) 0.0437(7) Uani 0.685(7) 1 d G U P A 1
H17A H 0.295017 0.860009 0.293442 0.052 Uiso 0.685(7) 1 calc R U P A 1
C18A C 0.2893(8) 0.7131(4) 0.1537(4) 0.0421(7) Uani 0.685(7) 1 d G U P A 1
H18A H 0.34699 0.785951 0.108149 0.051 Uiso 0.685(7) 1 calc R U P A 1
C14B C 0.213(2) 0.5262(13) 0.1158(10) 0.0491(19) Uani 0.315(7) 1 d D U P A 2
C15B C 0.133(2) 0.4482(9) 0.2028(12) 0.0514(18) Uani 0.315(7) 1 d . U P A 2
H15B H 0.084523 0.342402 0.191194 0.062 Uiso 0.315(7) 1 calc R U P A 2
C16B C 0.125(2) 0.5281(12) 0.3044(10) 0.0451(15) Uani 0.315(7) 1 d . U P A 2
H16B H 0.066701 0.467274 0.357164 0.054 Uiso 0.315(7) 1 calc R U P A 2
N2B N 0.179(2) 0.6611(11) 0.3402(11) 0.054(2) Uani 0.315(7) 1 d . U P A 2
C17B C 0.250(2) 0.7251(11) 0.2631(12) 0.0498(16) Uani 0.315(7) 1 d . U P A 2
H17B H 0.297516 0.830821 0.283201 0.06 Uiso 0.315(7) 1 calc R U P A 2
C18B C 0.2736(18) 0.6760(12) 0.1535(11) 0.0479(17) Uani 0.315(7) 1 d . U P A 2
H18B H 0.331021 0.745116 0.105171 0.058 Uiso 0.315(7) 1 calc R U P A 2
C19 C 0.246(3) 0.4054(18) -0.0767(15) 0.054(3) Uani 0.25 1 d D U P A 2
C20 C 0.2438(18) 0.474(2) 0.0117(10) 0.063(2) Uani 0.25 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   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 1.3576(12) . ?
O1 H1 0.83 . ?
O2 C3 1.3535(13) . ?
O2 H2A 0.83 . ?
N1 C7 1.3313(15) . ?
N1 C11 1.3388(14) . ?
C1 C2 1.3862(14) . ?
C1 C6 1.3913(13) . ?
C2 C3 1.3910(14) . ?
C2 H2 0.94 . ?
C3 C4 1.3959(13) . ?
C4 C5 1.3784(16) . ?
C4 H4 0.94 . ?
C5 C6 1.3838(16) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3776(14) . ?
C7 H7 0.94 . ?
C8 C9 1.3860(14) . ?
C8 H8 0.94 . ?
C9 C19 1.377(12) . ?
C9 C10 1.3887(16) . ?
C9 C12B 1.451(17) . ?
C9 C12A 1.500(4) . ?
C10 C11 1.3755(15) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12A C13A 1.340(4) . ?
C12A H12A 0.94 . ?
C13A C14A 1.499(3) . ?
C13A H13A 0.94 . ?
C12B C13B 1.268(18) . ?
C12B H12B 0.94 . ?
C13B C14B 1.447(17) . ?
C13B H13B 0.94 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.94 . ?
C16A N2A 1.39 . ?
C16A H16A 0.94 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.94 . ?
C18A H18A 0.94 . ?
C14B C18B 1.351(8) . ?
C14B C20 1.356(12) . ?
C14B C15B 1.398(9) . ?
C15B C16B 1.361(8) . ?
C15B H15B 0.94 . ?
C16B N2B 1.203(9) . ?
C16B C17B 1.939(13) . ?
C16B H16B 0.94 . ?
N2B C17B 1.215(7) . ?
C17B C18B 1.367(7) . ?
C17B H17B 0.94 . ?
C18B H18B 0.94 . ?
C19 C20 1.159(14) . ?

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 . . ?
C7 N1 C11 116.71(9) . . ?
O1 C1 C2 121.96(8) . . ?
O1 C1 C6 118.23(9) . . ?
C2 C1 C6 119.82(9) . . ?
C1 C2 C3 120.50(8) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O2 C3 C2 122.25(8) . . ?
O2 C3 C4 117.91(9) . . ?
C2 C3 C4 119.84(10) . . ?
C5 C4 C3 118.82(10) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.95(9) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.05(10) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.38(10) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.75(10) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C19 C9 C8 127.9(7) . . ?
C19 C9 C10 115.0(7) . . ?
C8 C9 C10 117.12(9) . . ?
C19 C9 C12B 16.5(4) . . ?
C8 C9 C12B 144.4(7) . . ?
C10 C9 C12B 98.5(7) . . ?
C8 C9 C12A 116.22(15) . . ?
C10 C9 C12A 126.59(16) . . ?
C11 C10 C9 119.18(10) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C11 C10 123.81(10) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13A C12A C9 122.5(3) . . ?
C13A C12A H12A 118.7 . . ?
C9 C12A H12A 118.7 . . ?
C12A C13A C14A 125.1(3) . . ?
C12A C13A H13A 117.5 . . ?
C14A C13A H13A 117.5 . . ?
C13B C12B C9 131(2) . . ?
C13B C12B H12B 114.4 . . ?
C9 C12B H12B 114.4 . . ?
C12B C13B C14B 135(2) . . ?
C12B C13B H13B 112.7 . . ?
C14B C13B H13B 112.7 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13A 122.0(2) . . ?
C18A C14A C13A 118.0(2) . . ?
C14A C15A C16A 120 . . ?
C14A C15A H15A 120 . . ?
C16A C15A H15A 120 . . ?
N2A C16A C15A 120 . . ?
N2A C16A H16A 120 . . ?
C15A C16A H16A 120 . . ?
C16A N2A C17A 120 . . ?
C18A C17A N2A 120 . . ?
C18A C17A H17A 120 . . ?
N2A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C20 120.5(10) . . ?
C18B C14B C15B 109.5(5) . . ?
C20 C14B C15B 129.9(9) . . ?
C18B C14B C13B 137.1(10) . . ?
C20 C14B C13B 17.2(5) . . ?
C15B C14B C13B 113.4(9) . . ?
C16B C15B C14B 118.9(5) . . ?
C16B C15B H15B 120.6 . . ?
C14B C15B H15B 120.6 . . ?
N2B C16B C15B 132.7(6) . . ?
N2B C16B C17B 36.9(3) . . ?
C15B C16B C17B 95.8(4) . . ?
N2B C16B H16B 113.7 . . ?
C15B C16B H16B 113.7 . . ?
C17B C16B H16B 150.6 . . ?
C16B N2B C17B 106.6(6) . . ?
N2B C17B C18B 133.6(7) . . ?
N2B C17B C16B 36.5(4) . . ?
C18B C17B C16B 97.1(5) . . ?
N2B C17B H17B 113.2 . . ?
C18B C17B H17B 113.2 . . ?
C16B C17B H17B 149.7 . . ?
C14B C18B C17B 118.8(6) . . ?
C14B C18B H18B 120.6 . . ?
C17B C18B H18B 120.6 . . ?
C20 C19 C9 171(2) . . ?
C19 C20 C14B 168(2) . . ?

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 2.7460(11) 175.7 1_556 yes
O2 H2A N2A^a 0.83 1.96 2.79(2) 177.2 2_666 yes
O2 H2A N2B^b 0.83 1.85 2.683(8) 176.9 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_BE75_BA25_230
_database_code_depnum_ccdc_archive 'CCDC 1995701'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT041_BE75_BA25_230       
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check 
RESPONSE: Due to a rounding error in the shelx program.
;
_vrf_PLAT155_BE75_BA25_230       
;
PROBLEM: The Triclinic Unitcell is NOT Reduced ..........     Please Do !  
RESPONSE: The unit cell was not reduced to maintain continuity throughout 
          the structures and temperatures.
;
# end Validation Reply Form

_audit_creation_date             2020-04-01T11:37:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C18.01 H15.51 N2 O2'
_chemical_formula_weight         291.96

#----------------------------------------------------------------------------#
#                   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                   8.13025(10)
_cell_length_b                   9.88487(15)
_cell_length_c                   10.90533(11)
_cell_angle_alpha                92.7008(14)
_cell_angle_beta                 107.5192(10)
_cell_angle_gamma                114.4022(12)
_cell_volume                     746.122(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    18371
_cell_measurement_theta_min      4.324
_cell_measurement_theta_max      77.138

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

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.066
_exptl_crystal_density_diffrn    1.3
_exptl_crystal_F_000             307
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 4 0 0.0556
-2 -6 -1 0.0374
0 3 6 0.0788
2 -4 0 0.0503
-5 0 0 0.0498
-1 -2 -7 0.0688
-5 -4 -1 0.0318
3 3 -4 0.0609
-2 -5 2 0.0477
1 -4 3 0.0598
2 5 -2 0.0622
-2 -4 3 0.0581
4 0 -2 0.0542
-2 0 5 0.0662
-1 4 4 0.0717
5 4 1 0.0337
-5 -3 -4 0.0659
1 -4 -5 0.0636

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

_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.92044
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.888
_shelx_estimated_absorpt_T_max   0.956

#----------------------------------------------------------------------------#
#                   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      -0.0955542
_diffrn_orient_matrix_ub_12      0.1048056
_diffrn_orient_matrix_ub_13      -0.1136552
_diffrn_orient_matrix_ub_21      0.1433627
_diffrn_orient_matrix_ub_22      0.0786195
_diffrn_orient_matrix_ub_23      -0.0451013
_diffrn_orient_matrix_ub_31      0.1241247
_diffrn_orient_matrix_ub_32      -0.1153859
_diffrn_orient_matrix_ub_33      -0.0887973
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_number            28182
_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       13
_diffrn_reflns_theta_min         4.337
_diffrn_reflns_theta_max         77.318
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.97
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.97
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.97
_reflns_Friedel_coverage         0
_reflns_number_total             3084
_reflns_number_gt                2814
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_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)+(0.0527P)²+0.0785P] 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(8)
_refine_ls_number_reflns         3084
_refine_ls_number_parameters     284
_refine_ls_number_restraints     579
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.031

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

_refine_special_details          
;
 To help model the substitution of the bis(4-pyridyl)acetylene with 
 1,2-bis(4-pyridyl)ethylene, the atom sites N2 and  C12 < C18, were split into
 parts A and B. The site associated with the rings were allowed to free refine
 their site occupancies to a total value of 1.0, while the C12 and C13 sites 
 were constrained to 0.75 and C19 and C20 (acetyl moiety) were constrained to
 0.25. To help maintain reasonable ADP and bond lengths, SIMU, RIGU, and DFIX 
 restraints and constraints were applied. At this temperature the ratio of the
 disordered BPE sites (A and B) were 0.69 and 0.06, 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 0.16716(10) 0.15317(8) 0.30482(7) 0.0473(2) Uani 1 1 d . . . . .
H1 H 0.199514 0.178602 0.38534 0.071 Uiso 1 1 calc R U . . .
O2 O 0.82162(11) 0.22580(10) 0.43168(7) 0.0544(2) Uani 1 1 d . . . . .
H2A H 0.826075 0.262101 0.503483 0.082 Uiso 1 1 calc R U . . .
N1 N 0.26195(13) 0.24517(11) -0.43144(8) 0.0481(2) Uani 1 1 d . . . . .
C1 C 0.31754(14) 0.15100(10) 0.27631(9) 0.0385(2) Uani 1 1 d . . . . .
C2 C 0.49402(14) 0.18846(10) 0.37301(9) 0.0390(2) Uani 1 1 d . . . . .
H2 H 0.511157 0.215155 0.461433 0.047 Uiso 1 1 calc R U . . .
C3 C 0.64603(14) 0.18686(11) 0.34027(9) 0.0413(2) Uani 1 1 d . . . . .
C4 C 0.61988(16) 0.14484(12) 0.20907(10) 0.0476(3) Uani 1 1 d . . . . .
H4 H 0.721083 0.14229 0.185871 0.057 Uiso 1 1 calc R U . . .
C5 C 0.44316(17) 0.10721(12) 0.11428(10) 0.0500(3) Uani 1 1 d . . . . .
H5 H 0.425277 0.079146 0.025929 0.06 Uiso 1 1 calc R U . . .
C6 C 0.29102(16) 0.10952(11) 0.14539(9) 0.0458(2) Uani 1 1 d . . . . .
H6 H 0.171722 0.083488 0.07911 0.055 Uiso 1 1 calc R U . . .
C7 C 0.19667(15) 0.14710(12) -0.35744(10) 0.0475(2) Uani 1 1 d . . . . .
H7 H 0.155697 0.043776 -0.387637 0.057 Uiso 1 1 calc R U . . .
C8 C 0.18632(15) 0.18979(12) -0.23881(10) 0.0450(2) Uani 1 1 d . . . . .
H8 H 0.138156 0.116278 -0.190525 0.054 Uiso 1 1 calc R U . . .
C9 C 0.24718(13) 0.34149(11) -0.19096(9) 0.0402(2) Uani 1 1 d D U . . .
C10 C 0.32099(15) 0.44467(12) -0.26574(10) 0.0466(2) Uani 1 1 d . . . . .
H10 H 0.368222 0.549089 -0.236117 0.056 Uiso 1 1 calc R U . . .
C11 C 0.32399(15) 0.39184(13) -0.38389(10) 0.0490(3) Uani 1 1 d . . . . .
H11 H 0.372383 0.462874 -0.433986 0.059 Uiso 1 1 calc R U . . .
C12A C 0.2173(8) 0.3774(4) -0.0663(4) 0.0358(6) Uani 0.695(7) 1 d D U P A 1
H12A H 0.161871 0.297574 -0.025563 0.043 Uiso 0.695(7) 1 calc R U P A 1
C13A C 0.2668(4) 0.5193(3) -0.0112(2) 0.0338(5) Uani 0.695(7) 1 d D U P A 1
H13A H 0.326277 0.598002 -0.051617 0.041 Uiso 0.695(7) 1 calc R U P A 1
C12B C 0.268(5) 0.445(2) -0.084(2) 0.040(3) Uani 0.060(7) 1 d D U P A 2
H12B H 0.343501 0.54713 -0.085648 0.048 Uiso 0.060(7) 1 calc R U P A 2
C13B C 0.208(4) 0.431(2) 0.011(2) 0.040(3) Uani 0.060(7) 1 d D U P A 2
H13B H 0.13744 0.328371 0.011701 0.048 Uiso 0.060(7) 1 calc R U P A 2
C14A C 0.2343(8) 0.5617(4) 0.1102(4) 0.0329(7) Uani 0.695(7) 1 d DG U P A 1
C15A C 0.1492(8) 0.4538(3) 0.1779(4) 0.0384(8) Uani 0.695(7) 1 d G U P A 1
H15A H 0.112322 0.351053 0.148725 0.046 Uiso 0.695(7) 1 calc R U P A 1
C16A C 0.1188(8) 0.4979(4) 0.2887(4) 0.0388(8) Uani 0.695(7) 1 d G U P A 1
H16A H 0.06124 0.424994 0.334498 0.047 Uiso 0.695(7) 1 calc R U P A 1
N2A N 0.1733(8) 0.6499(4) 0.3319(4) 0.0408(10) Uani 0.695(7) 1 d G U P A 1
C17A C 0.2584(8) 0.7578(3) 0.2642(4) 0.0402(7) Uani 0.695(7) 1 d G U P A 1
H17A H 0.295278 0.860571 0.293363 0.048 Uiso 0.695(7) 1 calc R U P A 1
C18A C 0.2888(7) 0.7137(4) 0.1534(4) 0.0380(7) Uani 0.695(7) 1 d G U P A 1
H18A H 0.346362 0.786632 0.10759 0.046 Uiso 0.695(7) 1 calc R U P A 1
C14B C 0.216(2) 0.5269(13) 0.1170(10) 0.0447(19) Uani 0.305(7) 1 d D U P A 2
C15B C 0.133(2) 0.4483(9) 0.2027(11) 0.0464(17) Uani 0.305(7) 1 d . U P A 2
H15B H 0.084985 0.342424 0.191054 0.056 Uiso 0.305(7) 1 calc R U P A 2
C16B C 0.124(2) 0.5279(12) 0.3036(10) 0.0409(16) Uani 0.305(7) 1 d . U P A 2
H16B H 0.063991 0.466319 0.3555 0.049 Uiso 0.305(7) 1 calc R U P A 2
N2B N 0.177(2) 0.6607(11) 0.3402(10) 0.050(2) Uani 0.305(7) 1 d . U P A 2
C17B C 0.2491(19) 0.7260(12) 0.2637(12) 0.0443(16) Uani 0.305(7) 1 d . U P A 2
H17B H 0.296197 0.831646 0.283834 0.053 Uiso 0.305(7) 1 calc R U P A 2
C18B C 0.2760(18) 0.6777(12) 0.1546(11) 0.0432(17) Uani 0.305(7) 1 d . U P A 2
H18B H 0.334932 0.74727 0.106936 0.052 Uiso 0.305(7) 1 calc R U P A 2
C19 C 0.245(3) 0.4027(18) -0.0767(15) 0.048(3) Uani 0.25 1 d D U P A 2
C20 C 0.2463(17) 0.4760(19) 0.0118(10) 0.0560(19) Uani 0.25 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   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 1.3571(12) . ?
O1 H1 0.83 . ?
O2 C3 1.3538(12) . ?
O2 H2A 0.83 . ?
N1 C7 1.3338(14) . ?
N1 C11 1.3389(14) . ?
C1 C2 1.3861(13) . ?
C1 C6 1.3927(13) . ?
C2 C3 1.3915(13) . ?
C2 H2 0.94 . ?
C3 C4 1.3974(13) . ?
C4 C5 1.3781(16) . ?
C4 H4 0.94 . ?
C5 C6 1.3859(16) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3793(14) . ?
C7 H7 0.94 . ?
C8 C9 1.3869(14) . ?
C8 H8 0.94 . ?
C9 C19 1.368(13) . ?
C9 C10 1.3902(15) . ?
C9 C12B 1.435(18) . ?
C9 C12A 1.502(4) . ?
C10 C11 1.3782(15) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12A C13A 1.341(5) . ?
C12A H12A 0.94 . ?
C13A C14A 1.499(3) . ?
C13A H13A 0.94 . ?
C12B C13B 1.265(18) . ?
C12B H12B 0.94 . ?
C13B C14B 1.430(17) . ?
C13B H13B 0.94 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.94 . ?
C16A N2A 1.39 . ?
C16A H16A 0.94 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.94 . ?
C18A H18A 0.94 . ?
C14B C18B 1.359(8) . ?
C14B C20 1.362(12) . ?
C14B C15B 1.393(9) . ?
C15B C16B 1.360(8) . ?
C15B H15B 0.94 . ?
C16B N2B 1.203(9) . ?
C16B C17B 1.938(14) . ?
C16B H16B 0.94 . ?
N2B C17B 1.220(8) . ?
C17B C18B 1.372(7) . ?
C17B H17B 0.94 . ?
C18B H18B 0.94 . ?
C19 C20 1.174(14) . ?

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 . . ?
C7 N1 C11 116.83(9) . . ?
O1 C1 C2 122.00(8) . . ?
O1 C1 C6 118.17(9) . . ?
C2 C1 C6 119.84(9) . . ?
C1 C2 C3 120.54(8) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O2 C3 C2 122.24(8) . . ?
O2 C3 C4 117.95(9) . . ?
C2 C3 C4 119.81(9) . . ?
C5 C4 C3 118.86(10) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.94(9) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.01(9) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.25(10) . . ?
N1 C7 H7 118.4 . . ?
C8 C7 H7 118.4 . . ?
C7 C8 C9 119.80(10) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C19 C9 C8 127.3(7) . . ?
C19 C9 C10 115.5(7) . . ?
C8 C9 C10 117.17(9) . . ?
C19 C9 C12B 16.6(4) . . ?
C8 C9 C12B 143.9(7) . . ?
C10 C9 C12B 98.9(7) . . ?
C8 C9 C12A 116.52(17) . . ?
C10 C9 C12A 126.23(18) . . ?
C11 C10 C9 119.12(10) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C11 C10 123.78(10) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13A C12A C9 122.4(3) . . ?
C13A C12A H12A 118.8 . . ?
C9 C12A H12A 118.8 . . ?
C12A C13A C14A 124.9(3) . . ?
C12A C13A H13A 117.6 . . ?
C14A C13A H13A 117.6 . . ?
C13B C12B C9 134(2) . . ?
C13B C12B H12B 112.8 . . ?
C9 C12B H12B 112.8 . . ?
C12B C13B C14B 138(2) . . ?
C12B C13B H13B 111 . . ?
C14B C13B H13B 111 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13A 121.9(2) . . ?
C18A C14A C13A 118.1(2) . . ?
C14A C15A C16A 120 . . ?
C14A C15A H15A 120 . . ?
C16A C15A H15A 120 . . ?
N2A C16A C15A 120 . . ?
N2A C16A H16A 120 . . ?
C15A C16A H16A 120 . . ?
C17A N2A C16A 120 . . ?
N2A C17A C18A 120 . . ?
N2A C17A H17A 120 . . ?
C18A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C20 119.8(10) . . ?
C18B C14B C15B 109.8(5) . . ?
C20 C14B C15B 130.4(9) . . ?
C18B C14B C13B 136.3(10) . . ?
C20 C14B C13B 17.2(4) . . ?
C15B C14B C13B 113.8(9) . . ?
C16B C15B C14B 118.6(5) . . ?
C16B C15B H15B 120.7 . . ?
C14B C15B H15B 120.7 . . ?
N2B C16B C15B 133.4(6) . . ?
N2B C16B C17B 37.2(4) . . ?
C15B C16B C17B 96.2(4) . . ?
N2B C16B H16B 113.3 . . ?
C15B C16B H16B 113.3 . . ?
C17B C16B H16B 150.5 . . ?
C16B N2B C17B 106.2(7) . . ?
N2B C17B C18B 133.5(7) . . ?
N2B C17B C16B 36.6(4) . . ?
C18B C17B C16B 97.0(5) . . ?
N2B C17B H17B 113.2 . . ?
C18B C17B H17B 113.2 . . ?
C16B C17B H17B 149.8 . . ?
C14B C18B C17B 118.4(6) . . ?
C14B C18B H18B 120.8 . . ?
C17B C18B H18B 120.8 . . ?
C20 C19 C9 169(2) . . ?
C19 C20 C14B 166(2) . . ?

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 2.7447(11) 175.6 1_556 yes
O2 H2A N2A^a 0.83 1.96 2.78(2) 177.2 2_666 yes
O2 H2A N2B^b 0.83 1.85 2.675(8) 177.2 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_BE75_BA25_270
_database_code_depnum_ccdc_archive 'CCDC 1995703'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT041_BE75_BA25_270       
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check 
RESPONSE: Due to a rounding error in the shelx program.
;
_vrf_PLAT911_BE75_BA25_270       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2020-04-01T11:39:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C18.01 H15.51 N2 O2'
_chemical_formula_weight         291.94

#----------------------------------------------------------------------------#
#                   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                   8.16783(10)
_cell_length_b                   9.90151(16)
_cell_length_c                   10.91446(11)
_cell_angle_alpha                92.8705(14)
_cell_angle_beta                 107.4858(10)
_cell_angle_gamma                114.3213(12)
_cell_volume                     751.686(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    17030
_cell_measurement_theta_min      4.327
_cell_measurement_theta_max      76.898

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

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.066
_exptl_crystal_density_diffrn    1.29
_exptl_crystal_F_000             307
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -6 0 0.0556
-2 6 0 0.0503
1 -5 4 0.0717
-5 1 1 0.0337
5 -1 -1 0.0318
-2 -3 -2 0.0622
5 -2 -4 0.0659
2 3 2 0.0477
1 1 -7 0.0688
-1 5 -5 0.0636
5 -5 0 0.0498
-3 0 -4 0.0609
0 -3 6 0.0788
2 -2 5 0.0662
2 5 -1 0.0374
-1 5 3 0.0598
-4 5 -2 0.0542
2 2 3 0.0581

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

_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.91455
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.956

#----------------------------------------------------------------------------#
#                   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      -0.009491
_diffrn_orient_matrix_ub_12      -0.104915
_diffrn_orient_matrix_ub_13      -0.1137767
_diffrn_orient_matrix_ub_21      -0.2208704
_diffrn_orient_matrix_ub_22      -0.0780316
_diffrn_orient_matrix_ub_23      -0.0451788
_diffrn_orient_matrix_ub_31      -0.0082619
_diffrn_orient_matrix_ub_32      0.115205
_diffrn_orient_matrix_ub_33      -0.08847
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_number            28189
_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       13
_diffrn_reflns_theta_min         4.334
_diffrn_reflns_theta_max         77.307
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_reflns_Friedel_coverage         0
_reflns_number_total             3100
_reflns_number_gt                2761
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_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)+(0.0546P)²+0.0621P] 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       0.0050(8)
_refine_ls_number_reflns         3100
_refine_ls_number_parameters     284
_refine_ls_number_restraints     579
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.1015
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.03

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

_refine_special_details          
;
 To help model the substitution of the bis(4-pyridyl)acetylene with 
 1,2-bis(4-pyridyl)ethylene, the atom sites N2 and  C12 < C18, were split into
 parts A and B. The site associated with the rings were allowed to free refine
 their site occupancies to a total value of 1.0, while the C12 and C13 sites 
 were constrained to 0.75 and C19 and C20 (acetyl moiety) were constrained to
 0.25. To help maintain reasonable ADP and bond lengths, SIMU, RIGU, and DFIX 
 restraints and constraints were applied. At this temperature the ratio of the
 disordered BPE sites (A and B) were 0.67 and 0.08, 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 0.16800(10) 0.15138(9) 0.30476(7) 0.0573(2) Uani 1 1 d . . . . .
H1 H 0.199662 0.176029 0.384327 0.086 Uiso 1 1 calc R U . . .
O2 O 0.81962(11) 0.22525(10) 0.43111(8) 0.0658(2) Uani 1 1 d . . . . .
H2A H 0.82333 0.259613 0.502368 0.099 Uiso 1 1 calc R U . . .
N1 N 0.26157(13) 0.24443(11) -0.43154(9) 0.0573(2) Uani 1 1 d . . . . .
C1 C 0.31784(14) 0.14969(10) 0.27609(9) 0.0460(2) Uani 1 1 d . . . . .
C2 C 0.49347(14) 0.18722(10) 0.37268(9) 0.0465(2) Uani 1 1 d . . . . .
H2 H 0.51023 0.213234 0.460181 0.056 Uiso 1 1 calc R U . . .
C3 C 0.64484(15) 0.18628(11) 0.33981(10) 0.0494(2) Uani 1 1 d . . . . .
C4 C 0.61874(17) 0.14468(12) 0.20880(10) 0.0571(3) Uani 1 1 d . . . . .
H4 H 0.718439 0.142375 0.18573 0.069 Uiso 1 1 calc R U . . .
C5 C 0.44325(18) 0.10713(13) 0.11427(10) 0.0598(3) Uani 1 1 d . . . . .
H5 H 0.425824 0.079888 0.026825 0.072 Uiso 1 1 calc R U . . .
C6 C 0.29196(17) 0.10872(12) 0.14548(10) 0.0549(3) Uani 1 1 d . . . . .
H6 H 0.174421 0.082708 0.079939 0.066 Uiso 1 1 calc R U . . .
C7 C 0.19673(16) 0.14783(13) -0.35727(11) 0.0573(3) Uani 1 1 d . . . . .
H7 H 0.155872 0.045571 -0.38685 0.069 Uiso 1 1 calc R U . . .
C8 C 0.18700(16) 0.19136(13) -0.23908(10) 0.0544(3) Uani 1 1 d . . . . .
H8 H 0.139616 0.119239 -0.191146 0.065 Uiso 1 1 calc R U . . .
C9 C 0.24784(14) 0.34266(12) -0.19160(10) 0.0488(2) Uani 1 1 d D U . . .
C10 C 0.32118(16) 0.44453(13) -0.26653(11) 0.0563(3) Uani 1 1 d . . . . .
H10 H 0.368122 0.547813 -0.237451 0.068 Uiso 1 1 calc R U . . .
C11 C 0.32359(16) 0.39095(14) -0.38423(11) 0.0590(3) Uani 1 1 d . . . . .
H11 H 0.371145 0.460636 -0.433953 0.071 Uiso 1 1 calc R U . . .
C12A C 0.2184(6) 0.3779(3) -0.0668(4) 0.0429(6) Uani 0.674(7) 1 d D U P A 1
H12A H 0.164674 0.298657 -0.026732 0.051 Uiso 0.674(7) 1 calc R U P A 1
C13A C 0.2661(3) 0.5183(3) -0.0110(2) 0.0413(5) Uani 0.674(7) 1 d D U P A 1
H13A H 0.324013 0.596157 -0.050931 0.05 Uiso 0.674(7) 1 calc R U P A 1
C12B C 0.274(4) 0.453(2) -0.083(2) 0.050(3) Uani 0.081(7) 1 d D U P A 2
H12B H 0.350751 0.55381 -0.078889 0.06 Uiso 0.081(7) 1 calc R U P A 2
C13B C 0.202(3) 0.424(2) 0.007(2) 0.050(3) Uani 0.081(7) 1 d D U P A 2
H13B H 0.128983 0.321135 0.001872 0.059 Uiso 0.081(7) 1 calc R U P A 2
C14A C 0.2343(8) 0.5610(4) 0.1105(4) 0.0397(8) Uani 0.674(7) 1 d DG U P A 1
C15A C 0.1503(8) 0.4535(3) 0.1782(4) 0.0467(8) Uani 0.674(7) 1 d G U P A 1
H15A H 0.11455 0.352062 0.149428 0.056 Uiso 0.674(7) 1 calc R U P A 1
C16A C 0.1199(8) 0.4977(4) 0.2890(4) 0.0466(9) Uani 0.674(7) 1 d G U P A 1
H16A H 0.063708 0.425779 0.3343 0.056 Uiso 0.674(7) 1 calc R U P A 1
N2A N 0.1734(8) 0.6494(4) 0.3320(4) 0.0483(11) Uani 0.674(7) 1 d G U P A 1
C17A C 0.2574(8) 0.7569(3) 0.2643(4) 0.0485(8) Uani 0.674(7) 1 d G U P A 1
H17A H 0.293157 0.858337 0.293059 0.058 Uiso 0.674(7) 1 calc R U P A 1
C18A C 0.2878(8) 0.7127(4) 0.1535(4) 0.0461(8) Uani 0.674(7) 1 d G U P A 1
H18A H 0.344 0.784622 0.108186 0.055 Uiso 0.674(7) 1 calc R U P A 1
C14B C 0.2125(18) 0.5223(12) 0.1170(9) 0.0531(19) Uani 0.326(7) 1 d D U P A 2
C15B C 0.1307(19) 0.4467(9) 0.2020(11) 0.0556(17) Uani 0.326(7) 1 d . U P A 2
H15B H 0.081158 0.342028 0.190512 0.067 Uiso 0.326(7) 1 calc R U P A 2
C16B C 0.1235(19) 0.5282(12) 0.3034(10) 0.0500(16) Uani 0.326(7) 1 d . U P A 2
H16B H 0.063152 0.468725 0.354871 0.06 Uiso 0.326(7) 1 calc R U P A 2
N2B N 0.1797(19) 0.6614(11) 0.3394(10) 0.060(2) Uani 0.326(7) 1 d . U P A 2
C17B C 0.2527(17) 0.7249(11) 0.2621(11) 0.0548(16) Uani 0.326(7) 1 d . U P A 2
H17B H 0.302239 0.829667 0.281828 0.066 Uiso 0.326(7) 1 calc R U P A 2
C18B C 0.2758(16) 0.6736(11) 0.1534(10) 0.0513(16) Uani 0.326(7) 1 d . U P A 2
H18B H 0.33368 0.740465 0.105276 0.062 Uiso 0.326(7) 1 calc R U P A 2
C19 C 0.245(2) 0.4082(18) -0.0783(14) 0.063(3) Uani 0.25 1 d D U P A 2
C20 C 0.2419(18) 0.4699(19) 0.0121(9) 0.068(2) Uani 0.25 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   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 1.3574(12) . ?
O1 H1 0.82 . ?
O2 C3 1.3538(13) . ?
O2 H2A 0.82 . ?
N1 C7 1.3307(15) . ?
N1 C11 1.3381(15) . ?
C1 C2 1.3857(14) . ?
C1 C6 1.3899(13) . ?
C2 C3 1.3903(14) . ?
C2 H2 0.93 . ?
C3 C4 1.3948(14) . ?
C4 C5 1.3752(17) . ?
C4 H4 0.93 . ?
C5 C6 1.3826(16) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.3749(15) . ?
C7 H7 0.93 . ?
C8 C9 1.3835(15) . ?
C8 H8 0.93 . ?
C9 C19 1.379(12) . ?
C9 C10 1.3872(16) . ?
C9 C12B 1.475(17) . ?
C9 C12A 1.501(3) . ?
C10 C11 1.3740(16) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12A C13A 1.335(4) . ?
C12A H12A 0.93 . ?
C13A C14A 1.499(3) . ?
C13A H13A 0.93 . ?
C12B C13B 1.271(18) . ?
C12B H12B 0.93 . ?
C13B C14B 1.466(16) . ?
C13B H13B 0.93 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.93 . ?
C16A N2A 1.39 . ?
C16A H16A 0.93 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.93 . ?
C18A H18A 0.93 . ?
C14B C20 1.358(11) . ?
C14B C18B 1.359(8) . ?
C14B C15B 1.378(8) . ?
C15B C16B 1.367(8) . ?
C15B H15B 0.93 . ?
C16B N2B 1.203(8) . ?
C16B C17B 1.948(13) . ?
C16B H16B 0.93 . ?
N2B C17B 1.229(7) . ?
C17B C18B 1.362(7) . ?
C17B H17B 0.93 . ?
C18B H18B 0.93 . ?
C19 C20 1.146(14) . ?

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 . . ?
C7 N1 C11 116.58(9) . . ?
O1 C1 C2 121.98(8) . . ?
O1 C1 C6 118.28(9) . . ?
C2 C1 C6 119.74(10) . . ?
C1 C2 C3 120.52(9) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O2 C3 C2 122.23(9) . . ?
O2 C3 C4 118.01(10) . . ?
C2 C3 C4 119.76(10) . . ?
C5 C4 C3 118.94(10) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.90(9) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.13(10) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N1 C7 C8 123.40(10) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.87(10) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C19 C9 C8 128.7(7) . . ?
C19 C9 C10 114.3(7) . . ?
C8 C9 C10 117.05(9) . . ?
C19 C9 C12B 16.3(5) . . ?
C8 C9 C12B 144.9(7) . . ?
C10 C9 C12B 98.0(7) . . ?
C8 C9 C12A 115.94(14) . . ?
C10 C9 C12A 126.94(15) . . ?
C11 C10 C9 119.18(10) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C11 C10 123.87(11) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13A C12A C9 122.6(3) . . ?
C13A C12A H12A 118.7 . . ?
C9 C12A H12A 118.7 . . ?
C12A C13A C14A 125.5(2) . . ?
C12A C13A H13A 117.2 . . ?
C14A C13A H13A 117.2 . . ?
C13B C12B C9 127(2) . . ?
C13B C12B H12B 116.5 . . ?
C9 C12B H12B 116.5 . . ?
C12B C13B C14B 132(2) . . ?
C12B C13B H13B 114.1 . . ?
C14B C13B H13B 114.1 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13A 121.9(2) . . ?
C18A C14A C13A 118.1(2) . . ?
C16A C15A C14A 120 . . ?
C16A C15A H15A 120 . . ?
C14A C15A H15A 120 . . ?
N2A C16A C15A 120 . . ?
N2A C16A H16A 120 . . ?
C15A C16A H16A 120 . . ?
C16A N2A C17A 120 . . ?
C18A C17A N2A 120 . . ?
C18A C17A H17A 120 . . ?
N2A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C20 C14B C18B 119.2(9) . . ?
C20 C14B C15B 130.6(8) . . ?
C18B C14B C15B 110.1(5) . . ?
C20 C14B C13B 16.8(5) . . ?
C18B C14B C13B 135.3(9) . . ?
C15B C14B C13B 114.4(8) . . ?
C16B C15B C14B 118.9(5) . . ?
C16B C15B H15B 120.6 . . ?
C14B C15B H15B 120.6 . . ?
N2B C16B C15B 132.8(6) . . ?
N2B C16B C17B 37.2(3) . . ?
C15B C16B C17B 95.6(4) . . ?
N2B C16B H16B 113.6 . . ?
C15B C16B H16B 113.6 . . ?
C17B C16B H16B 150.8 . . ?
C16B N2B C17B 106.5(6) . . ?
N2B C17B C18B 133.2(7) . . ?
N2B C17B C16B 36.3(4) . . ?
C18B C17B C16B 96.9(5) . . ?
N2B C17B H17B 113.4 . . ?
C18B C17B H17B 113.4 . . ?
C16B C17B H17B 149.7 . . ?
C14B C18B C17B 118.5(5) . . ?
C14B C18B H18B 120.7 . . ?
C17B C18B H18B 120.7 . . ?
C20 C19 C9 176(2) . . ?
C19 C20 C14B 171(2) . . ?

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 2.7476(11) 174.9 1_556 yes
O2 H2A N2A^a 0.82 1.97 2.79(2) 176.5 2_666 yes
O2 H2A N2B^b 0.82 1.87 2.690(8) 177.1 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_A50_BA50_210
_database_code_depnum_ccdc_archive 'CCDC 1995707'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT077_A50_BA50_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_PLAT906_A50_BA50_210        
;
PROBLEM: Large K Value in the Analysis of Variance ......      5.912 Check 
RESPONSE: Due to diffuse scattering about the Bragg peaks.
;
# end Validation Reply Form

_audit_creation_date             2019-11-11T13:38:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C16.95 H14 N3.05 O2'
_chemical_formula_weight         292.34

#----------------------------------------------------------------------------#
#                   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                   8.07384(14)
_cell_length_b                   9.7536(2)
_cell_length_c                   10.90755(17)
_cell_angle_alpha                92.9033(15)
_cell_angle_beta                 107.3262(15)
_cell_angle_gamma                114.0871(19)
_cell_volume                     733.82(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    7602
_cell_measurement_theta_min      4.289
_cell_measurement_theta_max      75.98

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

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.052
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             306
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 1 -7 0.0847
2 -1 5 0.0871
-2 -1 7 0.1232
1 -3 6 0.0981
0 -5 -1 0.0393
5 -3 -3 0.116
0 5 1 0.0131
-5 1 3 0.1027
-3 2 7 0.1163
5 -2 0 0.1098
0 -5 4 0.0805
4 2 -1 0.0622
5 -5 0 0.1116
-5 2 3 0.1092
-5 3 -2 0.1167


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

_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
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  0.458
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.847
_shelx_estimated_absorpt_T_max   0.963

#----------------------------------------------------------------------------#
#                   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      0.0456811
_diffrn_orient_matrix_ub_12      -0.0499692
_diffrn_orient_matrix_ub_13      0.1328509
_diffrn_orient_matrix_ub_21      -0.1201301
_diffrn_orient_matrix_ub_22      -0.1692422
_diffrn_orient_matrix_ub_23      -0.0700455
_diffrn_orient_matrix_ub_31      0.1823112
_diffrn_orient_matrix_ub_32      -0.003143
_diffrn_orient_matrix_ub_33      -0.0149396
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_number            15628
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_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         4.331
_diffrn_reflns_theta_max         77.188
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.961
_reflns_Friedel_coverage         0
_reflns_number_total             2992
_reflns_number_gt                2595
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_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)+(0.0510P)²+0.1640P] 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       0.0032(7)
_refine_ls_number_reflns         2992
_refine_ls_number_parameters     284
_refine_ls_number_restraints     513
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1206
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.154
_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 0.53 to 0.47 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 0.16622(14) 0.15250(12) 0.30951(10) 0.0504(3) Uani 1 1 d . . . . .
H1 H 0.198227 0.176136 0.390144 0.076 Uiso 1 1 calc R U . . .
O2 O 0.81950(16) 0.21452(14) 0.43466(11) 0.0591(3) Uani 1 1 d . . . . .
H2A H 0.824662 0.251694 0.506636 0.089 Uiso 1 1 calc R U . . .
N1 N 0.26212(18) 0.24603(16) -0.42547(13) 0.0517(3) Uani 1 1 d . . . . .
C1 C 0.3174(2) 0.15063(14) 0.27990(13) 0.0414(3) Uani 1 1 d . . . . .
C2 C 0.4923(2) 0.18202(15) 0.37664(13) 0.0412(3) Uani 1 1 d . . . . .
H2 H 0.507711 0.204497 0.465317 0.049 Uiso 1 1 calc R U . . .
C3 C 0.6447(2) 0.18039(16) 0.34301(14) 0.0452(3) Uani 1 1 d . . . . .
C4 C 0.6204(2) 0.14307(17) 0.21218(16) 0.0524(4) Uani 1 1 d . . . . .
H4 H 0.72145 0.139014 0.188612 0.063 Uiso 1 1 calc R U . . .
C5 C 0.4451(3) 0.11198(18) 0.11716(15) 0.0545(4) Uani 1 1 d . . . . .
H5 H 0.428707 0.087443 0.028534 0.065 Uiso 1 1 calc R U . . .
C6 C 0.2935(2) 0.11597(17) 0.14886(14) 0.0499(4) Uani 1 1 d . . . . .
H6 H 0.176027 0.095539 0.082734 0.06 Uiso 1 1 calc R U . . .
C7 C 0.3281(2) 0.39545(19) -0.37924(18) 0.0580(4) Uani 1 1 d . . . . .
H7 H 0.37716 0.465368 -0.430431 0.07 Uiso 1 1 calc R U . . .
C8 C 0.3283(2) 0.45247(18) -0.26161(17) 0.0561(4) Uani 1 1 d . . . . .
H8 H 0.378415 0.558523 -0.232347 0.067 Uiso 1 1 calc R U . . .
C9 C 0.2526(2) 0.34933(17) -0.18693(14) 0.0453(3) Uani 1 1 d D . . . .
C10 C 0.1864(2) 0.19432(16) -0.23240(14) 0.0463(3) Uani 1 1 d . . . . .
H10 H 0.13667 0.121882 -0.183198 0.056 Uiso 1 1 calc R U . . .
C11 C 0.1948(2) 0.14866(17) -0.35075(15) 0.0481(3) Uani 1 1 d . . . . .
H11 H 0.150974 0.043555 -0.38061 0.058 Uiso 1 1 calc R U . . .
N2A N 0.2149(13) 0.3791(8) -0.0595(8) 0.0417(15) Uani 0.482(13) 1 d D U P A 1
N3A N 0.2657(6) 0.5132(7) -0.0169(7) 0.0432(13) Uani 0.482(13) 1 d D U P A 1
C12A C 0.2312(13) 0.5525(9) 0.0986(8) 0.0359(11) Uani 0.482(13) 1 d . U P A 1
C13A C 0.2806(17) 0.7048(9) 0.1449(9) 0.0456(16) Uani 0.482(13) 1 d . U P A 1
H13A H 0.33468 0.782592 0.101224 0.055 Uiso 0.482(13) 1 calc R U P A 1
C14A C 0.247(2) 0.7371(10) 0.2576(12) 0.0490(19) Uani 0.482(13) 1 d . U P A 1
H14A H 0.28264 0.840466 0.288303 0.059 Uiso 0.482(13) 1 calc R U P A 1
N4A N 0.1728(17) 0.6416(10) 0.3244(9) 0.0446(13) Uani 0.482(13) 1 d . U P A 1
C15A C 0.1249(12) 0.4997(8) 0.2780(8) 0.0416(13) Uani 0.482(13) 1 d . U P A 1
H15A H 0.068626 0.425922 0.324157 0.05 Uiso 0.482(13) 1 calc R U P A 1
C16A C 0.1487(11) 0.4475(7) 0.1680(8) 0.0400(13) Uani 0.482(13) 1 d . U P A 1
H16A H 0.109505 0.342643 0.140915 0.048 Uiso 0.482(13) 1 calc R U P A 1
C12B C 0.2132(11) 0.5276(8) 0.1265(6) 0.0371(14) Uani 0.518(13) 1 d DG U P A 2
C13B C 0.2839(15) 0.6860(8) 0.1532(9) 0.0479(18) Uani 0.518(13) 1 d G U P A 2
H13B H 0.345127 0.745326 0.100266 0.058 Uiso 0.518(13) 1 calc R U P A 2
C14B C 0.2639(18) 0.7565(6) 0.2582(10) 0.0446(18) Uani 0.518(13) 1 d G U P A 2
H14B H 0.311742 0.863614 0.276315 0.054 Uiso 0.518(13) 1 calc R U P A 2
N4B N 0.1734(16) 0.6687(8) 0.3365(8) 0.0470(14) Uani 0.518(13) 1 d G U P A 2
C15B C 0.1027(10) 0.5104(8) 0.3098(7) 0.0422(13) Uani 0.518(13) 1 d G U P A 2
H15B H 0.041406 0.451014 0.362706 0.051 Uiso 0.518(13) 1 calc R U P A 2
C16B C 0.1226(9) 0.4398(6) 0.2047(7) 0.0409(13) Uani 0.518(13) 1 d G U P A 2
H16B H 0.07479 0.332723 0.186657 0.049 Uiso 0.518(13) 1 calc R U P A 2
C17 C 0.2330(9) 0.4619(10) 0.0186(6) 0.0415(16) Uani 0.474(17) 1 d D U P A 2
C18 C 0.2531(16) 0.4140(12) -0.0772(9) 0.0455(18) Uani 0.474(17) 1 d D U P A 2
N2B N 0.274(7) 0.478(7) -0.068(6) 0.050(6) Uani 0.042(6) 1 d D U P A 3
N3B N 0.175(7) 0.387(8) -0.012(6) 0.056(8) Uani 0.042(6) 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 1.3589(17) . ?
O1 H1 0.83 . ?
O2 C3 1.3583(18) . ?
O2 H2A 0.83 . ?
N1 C11 1.335(2) . ?
N1 C7 1.339(2) . ?
C1 C2 1.3884(19) . ?
C1 C6 1.389(2) . ?
C2 C3 1.390(2) . ?
C2 H2 0.94 . ?
C3 C4 1.389(2) . ?
C4 C5 1.383(2) . ?
C4 H4 0.94 . ?
C5 C6 1.382(2) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.371(2) . ?
C7 H7 0.94 . ?
C8 C9 1.388(2) . ?
C8 H8 0.94 . ?
C9 C18 1.322(9) . ?
C9 C10 1.387(2) . ?
C9 N2A 1.547(8) . ?
C9 N2B 1.68(8) . ?
C10 C11 1.374(2) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
N2A N3A 1.218(9) . ?
N3A C12A 1.436(8) . ?
C12A C16A 1.373(6) . ?
C12A C13A 1.393(6) . ?
C13A C14A 1.383(6) . ?
C13A H13A 0.94 . ?
C14A N4A 1.277(7) . ?
C14A H14A 0.94 . ?
N4A C15A 1.302(7) . ?
C15A C16A 1.376(6) . ?
C15A H15A 0.94 . ?
C16A H16A 0.94 . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
C12B C17 1.392(6) . ?
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(11) . ?
N2B N3B 1.24(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 117.17(14) . . ?
O1 C1 C2 121.76(12) . . ?
O1 C1 C6 118.27(13) . . ?
C2 C1 C6 119.96(13) . . ?
C1 C2 C3 120.34(13) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C4 118.05(14) . . ?
O2 C3 C2 122.03(13) . . ?
C4 C3 C2 119.91(14) . . ?
C5 C4 C3 118.93(15) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C6 C5 C4 121.84(14) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 118.99(14) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.87(15) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.20(14) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C18 C9 C10 127.3(5) . . ?
C18 C9 C8 114.1(5) . . ?
C10 C9 C8 118.66(14) . . ?
C10 C9 N2A 111.9(3) . . ?
C8 C9 N2A 129.3(3) . . ?
C10 C9 N2B 144.1(14) . . ?
C8 C9 N2B 97.1(14) . . ?
C11 C10 C9 118.74(14) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.31(14) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
N3A N2A C9 114.7(9) . . ?
N2A N3A C12A 119.1(9) . . ?
C16A C12A C13A 116.6(4) . . ?
C16A C12A N3A 123.8(5) . . ?
C13A C12A N3A 119.6(6) . . ?
C14A C13A C12A 117.4(5) . . ?
C14A C13A H13A 121.3 . . ?
C12A C13A H13A 121.3 . . ?
N4A C14A C13A 127.1(6) . . ?
N4A C14A H14A 116.5 . . ?
C13A C14A H14A 116.5 . . ?
C14A N4A C15A 114.4(5) . . ?
N4A C15A C16A 126.2(5) . . ?
N4A C15A H15A 116.9 . . ?
C16A C15A H15A 116.9 . . ?
C12A C16A C15A 118.3(4) . . ?
C12A C16A H16A 120.8 . . ?
C15A C16A H16A 120.8 . . ?
C13B C12B C16B 120 . . ?
C13B C12B C17 117.9(5) . . ?
C16B C12B C17 122.1(5) . . ?
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 . . ?
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 175.8(12) . . ?
C17 C18 C9 173.0(12) . . ?
N3B N2B C9 99(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -179.47(12) . . . . ?
C6 C1 C2 C3 0.6(2) . . . . ?
C1 C2 C3 O2 178.20(13) . . . . ?
C1 C2 C3 C4 -1.8(2) . . . . ?
O2 C3 C4 C5 -178.28(14) . . . . ?
C2 C3 C4 C5 1.7(2) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
O1 C1 C6 C5 -179.31(13) . . . . ?
C2 C1 C6 C5 0.6(2) . . . . ?
C11 N1 C7 C8 -0.6(2) . . . . ?
N1 C7 C8 C9 -1.2(2) . . . . ?
C7 C8 C9 C18 -178.0(6) . . . . ?
C7 C8 C9 C10 2.1(2) . . . . ?
C7 C8 C9 N2A -173.0(4) . . . . ?
C7 C8 C9 N2B -175.8(19) . . . . ?
C18 C9 C10 C11 178.8(6) . . . . ?
C8 C9 C10 C11 -1.2(2) . . . . ?
N2A C9 C10 C11 174.6(4) . . . . ?
N2B C9 C10 C11 175(3) . . . . ?
C7 N1 C11 C10 1.6(2) . . . . ?
C9 C10 C11 N1 -0.7(2) . . . . ?
C10 C9 N2A N3A -178.2(5) . . . . ?
C8 C9 N2A N3A -2.8(9) . . . . ?
C9 N2A N3A C12A 177.9(6) . . . . ?
N2A N3A C12A C16A 2.1(10) . . . . ?
N2A N3A C12A C13A -177.1(7) . . . . ?
C16A C12A C13A C14A 1.6(6) . . . . ?
N3A C12A C13A C14A -179.1(8) . . . . ?
C12A C13A C14A N4A -0.8(7) . . . . ?
C13A C14A N4A C15A -0.3(6) . . . . ?
C14A N4A C15A C16A 0.6(6) . . . . ?
C13A C12A C16A C15A -1.3(5) . . . . ?
N3A C12A C16A C15A 179.4(7) . . . . ?
N4A C15A C16A C12A 0.3(6) . . . . ?
C16B C12B C13B C14B 0 . . . . ?
C17 C12B C13B C14B 178.7(7) . . . . ?
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 -178.7(7) . . . . ?
C10 C9 N2B N3B -9(6) . . . . ?
C8 C9 N2B N3B 168(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 0.83 1.93 2.7588(17) 174.2 1_556 yes
O2 H2A N4A^a 0.83 2.06 2.887(8) 174.2 2_666 yes
O2 H2A N4B^b 0.83 1.84 2.67(4) 178 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_A50_BA50_270
_database_code_depnum_ccdc_archive 'CCDC 1995710'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT077_A50_BA50_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_A50_BA50_270        
;
PROBLEM: Large K Value in the Analysis of Variance ......      9.023 Check 
RESPONSE: Due to diffuse scattering about the Bragg peaks.
;
# end Validation Reply Form

_audit_creation_date             2019-11-11T13:45:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C16.92 H14 N3.07 O2'
_chemical_formula_weight         292.33

#----------------------------------------------------------------------------#
#                   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                   8.1172(2)
_cell_length_b                   9.7795(3)
_cell_length_c                   10.9256(2)
_cell_angle_alpha                93.2084(19)
_cell_angle_beta                 107.177(2)
_cell_angle_gamma                113.972(3)
_cell_volume                     741.59(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    6624
_cell_measurement_theta_min      4.272
_cell_measurement_theta_max      75.236

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

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.052
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             306
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 1 -7 0.0847
2 -1 6 0.0871
-2 -1 7 0.1232
1 -3 6 0.0981
0 -5 -2 0.0393
5 -3 -3 0.116
0 5 2 0.0131
-5 2 2 0.1027
-3 1 7 0.1163
5 -3 0 0.1098
0 -5 4 0.0805
4 2 -1 0.0622
5 -5 -1 0.1116
-5 2 3 0.1092
-5 4 -1 0.1167


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

_exptl_absorpt_coefficient_mu    0.72
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
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  0.464
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.848
_shelx_estimated_absorpt_T_max   0.964

#----------------------------------------------------------------------------#
#                   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      0.032297
_diffrn_orient_matrix_ub_12      -0.0671574
_diffrn_orient_matrix_ub_13      0.1242833
_diffrn_orient_matrix_ub_21      -0.1250316
_diffrn_orient_matrix_ub_22      -0.1626247
_diffrn_orient_matrix_ub_23      -0.0837231
_diffrn_orient_matrix_ub_31      0.1800978
_diffrn_orient_matrix_ub_32      -0.0048575
_diffrn_orient_matrix_ub_33      -0.0157707
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_number            15831
_diffrn_reflns_limit_h_min       -8
_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         4.324
_diffrn_reflns_theta_max         77.279
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.961
_reflns_Friedel_coverage         0
_reflns_number_total             3029
_reflns_number_gt                2488
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_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)+(0.0626P)²+0.1053P] 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       0.0034(9)
_refine_ls_number_reflns         3029
_refine_ls_number_parameters     284
_refine_ls_number_restraints     507
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1336
_refine_ls_wR_factor_gt          0.1264
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.132
_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)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 0.54 to 0.46 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 0.16787(15) 0.15070(13) 0.30971(11) 0.0644(3) Uani 1 1 d . . . . .
H1 H 0.199419 0.174855 0.389212 0.097 Uiso 1 1 calc R U . . .
O2 O 0.81695(17) 0.21434(16) 0.43383(12) 0.0755(4) Uani 1 1 d . . . . .
H2A H 0.822755 0.252712 0.504599 0.113 Uiso 1 1 calc R U . . .
N1 N 0.26151(19) 0.24531(17) -0.42531(13) 0.0643(4) Uani 1 1 d . . . . .
C1 C 0.3184(2) 0.14922(15) 0.28008(14) 0.0520(3) Uani 1 1 d . . . . .
C2 C 0.4920(2) 0.18105(15) 0.37629(14) 0.0524(3) Uani 1 1 d . . . . .
H2 H 0.50703 0.203341 0.463916 0.063 Uiso 1 1 calc R U . . .
C3 C 0.6433(2) 0.17987(17) 0.34266(15) 0.0571(4) Uani 1 1 d . . . . .
C4 C 0.6194(3) 0.14311(19) 0.21209(17) 0.0662(4) Uani 1 1 d . . . . .
H4 H 0.719115 0.139716 0.188629 0.079 Uiso 1 1 calc R U . . .
C5 C 0.4462(3) 0.11177(19) 0.11785(16) 0.0692(4) Uani 1 1 d . . . . .
H5 H 0.430337 0.087847 0.03026 0.083 Uiso 1 1 calc R U . . .
C6 C 0.2951(3) 0.11483(18) 0.14957(15) 0.0634(4) Uani 1 1 d . . . . .
H6 H 0.17946 0.09411 0.08431 0.076 Uiso 1 1 calc R U . . .
C7 C 0.3278(2) 0.3945(2) -0.37985(19) 0.0706(5) Uani 1 1 d . . . . .
H7 H 0.376017 0.462617 -0.430749 0.085 Uiso 1 1 calc R U . . .
C8 C 0.3286(2) 0.45239(19) -0.26286(18) 0.0685(4) Uani 1 1 d . . . . .
H8 H 0.378233 0.557199 -0.234234 0.082 Uiso 1 1 calc R U . . .
C9 C 0.2535(2) 0.35082(18) -0.18784(15) 0.0567(4) Uani 1 1 d D . . . .
C10 C 0.1870(2) 0.19634(18) -0.23284(15) 0.0601(4) Uani 1 1 d . . . . .
H10 H 0.137838 0.125563 -0.184048 0.072 Uiso 1 1 calc R U . . .
C11 C 0.1948(2) 0.14970(19) -0.35043(16) 0.0619(4) Uani 1 1 d . . . . .
H11 H 0.151329 0.045782 -0.379634 0.074 Uiso 1 1 calc R U . . .
N2A N 0.2141(14) 0.3790(9) -0.0598(8) 0.0522(16) Uani 0.453(14) 1 d D U P A 1
N3A N 0.2649(8) 0.5123(8) -0.0159(8) 0.0551(15) Uani 0.453(14) 1 d D U P A 1
C12A C 0.2320(16) 0.5552(10) 0.1023(9) 0.0462(13) Uani 0.453(14) 1 d . U P A 1
C13A C 0.2804(18) 0.7056(10) 0.1498(10) 0.0575(17) Uani 0.453(14) 1 d . U P A 1
H13A H 0.334133 0.78316 0.107678 0.069 Uiso 0.453(14) 1 calc R U P A 1
C14A C 0.246(2) 0.7362(10) 0.2626(12) 0.061(2) Uani 0.453(14) 1 d . U P A 1
H14A H 0.280794 0.838024 0.294327 0.073 Uiso 0.453(14) 1 calc R U P A 1
N4A N 0.171(2) 0.6410(13) 0.3269(11) 0.0604(18) Uani 0.453(14) 1 d . U P A 1
C15A C 0.1253(17) 0.5021(11) 0.2784(10) 0.0579(17) Uani 0.453(14) 1 d . U P A 1
H15A H 0.069234 0.428588 0.322964 0.07 Uiso 0.453(14) 1 calc R U P A 1
C16A C 0.1488(14) 0.4497(8) 0.1697(9) 0.0538(16) Uani 0.453(14) 1 d . U P A 1
H16A H 0.109736 0.346119 0.142286 0.065 Uiso 0.453(14) 1 calc R U P A 1
C12B C 0.2103(13) 0.5216(8) 0.1227(7) 0.0499(15) Uani 0.547(14) 1 d DG U P A 2
C13B C 0.2809(14) 0.6796(8) 0.1485(8) 0.0603(18) Uani 0.547(14) 1 d G U P A 2
H13B H 0.33945 0.736914 0.095111 0.072 Uiso 0.547(14) 1 calc R U P A 2
C14B C 0.2640(18) 0.7519(7) 0.2542(10) 0.062(2) Uani 0.547(14) 1 d G U P A 2
H14B H 0.311211 0.857593 0.271427 0.074 Uiso 0.547(14) 1 calc R U P A 2
N4B N 0.1765(18) 0.6662(9) 0.3340(9) 0.0610(16) Uani 0.547(14) 1 d G U P A 2
C15B C 0.1059(13) 0.5081(9) 0.3082(8) 0.0583(15) Uani 0.547(14) 1 d G U P A 2
H15B H 0.047407 0.450804 0.361663 0.07 Uiso 0.547(14) 1 calc R U P A 2
C16B C 0.1229(12) 0.4358(7) 0.2026(8) 0.0578(15) Uani 0.547(14) 1 d G U P A 2
H16B H 0.075644 0.330122 0.185347 0.069 Uiso 0.547(14) 1 calc R U P A 2
C17 C 0.2317(12) 0.4608(15) 0.0172(7) 0.0529(19) Uani 0.46(2) 1 d D U P A 2
C18 C 0.2549(16) 0.4150(16) -0.0775(9) 0.055(2) Uani 0.46(2) 1 d D U P A 2
N2B N 0.271(5) 0.472(5) -0.074(3) 0.057(5) Uani 0.082(11) 1 d D U P A 3
N3B N 0.191(5) 0.400(5) -0.001(4) 0.060(6) Uani 0.082(11) 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 1.3587(18) . ?
O1 H1 0.82 . ?
O2 C3 1.3561(19) . ?
O2 H2A 0.82 . ?
N1 C11 1.331(2) . ?
N1 C7 1.337(2) . ?
C1 C6 1.385(2) . ?
C1 C2 1.385(2) . ?
C2 C3 1.387(2) . ?
C2 H2 0.93 . ?
C3 C4 1.387(2) . ?
C4 C5 1.375(3) . ?
C4 H4 0.93 . ?
C5 C6 1.380(2) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.366(3) . ?
C7 H7 0.93 . ?
C8 C9 1.387(2) . ?
C8 H8 0.93 . ?
C9 C18 1.322(9) . ?
C9 C10 1.383(2) . ?
C9 N2A 1.558(9) . ?
C9 N2B 1.60(5) . ?
C10 C11 1.367(2) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
N2A N3A 1.215(10) . ?
N3A C12A 1.466(10) . ?
C12A C16A 1.370(7) . ?
C12A C13A 1.383(7) . ?
C13A C14A 1.386(7) . ?
C13A H13A 0.93 . ?
C14A N4A 1.261(9) . ?
C14A H14A 0.93 . ?
N4A C15A 1.287(8) . ?
C15A C16A 1.361(8) . ?
C15A H15A 0.93 . ?
C16A H16A 0.93 . ?
C12B C17 1.356(8) . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
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 1.199(12) . ?
N2B N3B 1.24(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 117.25(14) . . ?
O1 C1 C6 118.25(14) . . ?
O1 C1 C2 121.82(13) . . ?
C6 C1 C2 119.93(14) . . ?
C1 C2 C3 120.36(13) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.09(14) . . ?
O2 C3 C4 118.08(14) . . ?
C2 C3 C4 119.83(15) . . ?
C5 C4 C3 119.02(16) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.86(15) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 118.98(15) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.69(16) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 118.27(15) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C18 C9 C10 126.6(6) . . ?
C18 C9 C8 114.8(6) . . ?
C10 C9 C8 118.62(15) . . ?
C10 C9 N2A 110.8(3) . . ?
C8 C9 N2A 130.4(3) . . ?
C10 C9 N2B 143.1(9) . . ?
C8 C9 N2B 98.1(9) . . ?
C11 C10 C9 118.71(15) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.41(15) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
N3A N2A C9 114.6(11) . . ?
N2A N3A C12A 120.5(11) . . ?
C16A C12A C13A 116.5(5) . . ?
C16A C12A N3A 122.3(6) . . ?
C13A C12A N3A 121.1(6) . . ?
C12A C13A C14A 117.3(6) . . ?
C12A C13A H13A 121.4 . . ?
C14A C13A H13A 121.4 . . ?
N4A C14A C13A 127.1(5) . . ?
N4A C14A H14A 116.5 . . ?
C13A C14A H14A 116.5 . . ?
C14A N4A C15A 113.8(5) . . ?
N4A C15A C16A 127.8(6) . . ?
N4A C15A H15A 116.1 . . ?
C16A C15A H15A 116.1 . . ?
C15A C16A C12A 117.5(5) . . ?
C15A C16A H16A 121.3 . . ?
C12A C16A H16A 121.3 . . ?
C17 C12B C13B 116.0(6) . . ?
C17 C12B C16B 124.0(6) . . ?
C13B C12B C16B 120 . . ?
C12B C13B C14B 120 . . ?
C12B C13B H13B 120 . . ?
C14B 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 176.4(18) . . ?
C17 C18 C9 171.6(14) . . ?
N3B N2B C9 108(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 -179.44(12) . . . . ?
C6 C1 C2 C3 0.5(2) . . . . ?
C1 C2 C3 O2 178.23(13) . . . . ?
C1 C2 C3 C4 -1.5(2) . . . . ?
O2 C3 C4 C5 -178.28(15) . . . . ?
C2 C3 C4 C5 1.5(2) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
O1 C1 C6 C5 -179.54(14) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
C11 N1 C7 C8 -0.7(2) . . . . ?
N1 C7 C8 C9 -1.2(3) . . . . ?
C7 C8 C9 C18 -178.4(5) . . . . ?
C7 C8 C9 C10 2.0(2) . . . . ?
C7 C8 C9 N2A -172.6(5) . . . . ?
C7 C8 C9 N2B -175.3(13) . . . . ?
C18 C9 C10 C11 179.4(6) . . . . ?
C8 C9 C10 C11 -1.1(2) . . . . ?
N2A C9 C10 C11 174.5(4) . . . . ?
N2B C9 C10 C11 174(2) . . . . ?
C7 N1 C11 C10 1.7(2) . . . . ?
C9 C10 C11 N1 -0.8(2) . . . . ?
C10 C9 N2A N3A -178.4(6) . . . . ?
C8 C9 N2A N3A -3.5(10) . . . . ?
C9 N2A N3A C12A 178.4(7) . . . . ?
N2A N3A C12A C16A 1.8(12) . . . . ?
N2A N3A C12A C13A -176.8(8) . . . . ?
C16A C12A C13A C14A 1.8(6) . . . . ?
N3A C12A C13A C14A -179.6(10) . . . . ?
C12A C13A C14A N4A -1.0(7) . . . . ?
C13A C14A N4A C15A -0.1(7) . . . . ?
C14A N4A C15A C16A 0.5(7) . . . . ?
N4A C15A C16A C12A 0.4(8) . . . . ?
C13A C12A C16A C15A -1.5(7) . . . . ?
N3A C12A C16A C15A 179.9(10) . . . . ?
C17 C12B C13B C14B 179.5(8) . . . . ?
C16B C12B C13B C14B 0 . . . . ?
C12B C13B C14B N4B 0 . . . . ?
C13B C14B N4B C15B 0 . . . . ?
C14B N4B C15B C16B 0 . . . . ?
N4B C15B C16B C12B 0 . . . . ?
C17 C12B C16B C15B -179.4(9) . . . . ?
C13B C12B C16B C15B 0 . . . . ?
C10 C9 N2B N3B -3(5) . . . . ?
C8 C9 N2B N3B 173(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 1.95 2.7649(17) 174.3 1_556 yes
O2 H2A N4A^a 0.82 2.04 2.860(8) 175.4 2_666 yes
O2 H2A N4B^b 0.82 1.89 2.71(4) 177.2 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_A50_BA50_290
_database_code_depnum_ccdc_archive 'CCDC 1995711'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT041_A50_BA50_290        
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)acetylene molecules.
;
_vrf_PLAT077_A50_BA50_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_A50_BA50_290        
;
PROBLEM: Large K Value in the Analysis of Variance ......      9.399 Check 
RESPONSE: Due to diffuse scattering about the Bragg peaks.
;
# end Validation Reply Form

_audit_creation_date             2019-11-11T13:46:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C16.90 H14 N3.08 O2'
_chemical_formula_weight         292.27

#----------------------------------------------------------------------------#
#                   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                   8.1338(2)
_cell_length_b                   9.7910(3)
_cell_length_c                   10.9340(3)
_cell_angle_alpha                93.322(2)
_cell_angle_beta                 107.125(2)
_cell_angle_gamma                113.929(3)
_cell_volume                     744.78(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    6276
_cell_measurement_theta_min      4.291
_cell_measurement_theta_max      76.275

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

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.052
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             306
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 1 -7 0.0847
2 -1 6 0.0871
-2 -1 7 0.1232
1 -3 6 0.0981
0 -5 -2 0.0393
5 -3 -3 0.116
0 5 2 0.0131
-5 2 2 0.1027
-3 1 7 0.1163
5 -3 0 0.1098
0 -5 4 0.0805
4 1 -1 0.0622
5 -5 -1 0.1116
-5 2 3 0.1092
-5 4 -1 0.1167


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

_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
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  0.462
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.849
_shelx_estimated_absorpt_T_max   0.964

#----------------------------------------------------------------------------#
#                   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      0.0309784
_diffrn_orient_matrix_ub_12      -0.0681944
_diffrn_orient_matrix_ub_13      0.1234994
_diffrn_orient_matrix_ub_21      -0.1269589
_diffrn_orient_matrix_ub_22      -0.1618938
_diffrn_orient_matrix_ub_23      -0.0845225
_diffrn_orient_matrix_ub_31      0.178305
_diffrn_orient_matrix_ub_32      -0.0068611
_diffrn_orient_matrix_ub_33      -0.0165897
_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     0.0519
_diffrn_reflns_number            15615
_diffrn_reflns_limit_h_min       -8
_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         4.321
_diffrn_reflns_theta_max         77.947
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.955
_reflns_Friedel_coverage         0
_reflns_number_total             3043
_reflns_number_gt                2418
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_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)+(0.0522P)²+0.1133P] 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       0.0035(7)
_refine_ls_number_reflns         3043
_refine_ls_number_parameters     284
_refine_ls_number_restraints     507
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1251
_refine_ls_wR_factor_gt          0.1175
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.133
_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)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 0.55 to 0.45 with the amount 
 of 4,4'-azopyridine in the secondary position calculated at 0.10. 
;

#----------------------------------------------------------------------------#
#                   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 0.16836(15) 0.14984(13) 0.30983(11) 0.0695(3) Uani 1 1 d . . . . .
H1 H 0.199393 0.173041 0.389337 0.104 Uiso 1 1 calc R U . . .
O2 O 0.81624(17) 0.21430(16) 0.43359(12) 0.0816(4) Uani 1 1 d . . . . .
H2A H 0.821198 0.250985 0.504695 0.122 Uiso 1 1 calc R U . . .
N1 N 0.26145(19) 0.24508(17) -0.42528(13) 0.0687(4) Uani 1 1 d . . . . .
C1 C 0.3186(2) 0.14874(15) 0.28021(14) 0.0557(3) Uani 1 1 d . . . . .
C2 C 0.4919(2) 0.18067(15) 0.37623(14) 0.0559(3) Uani 1 1 d . . . . .
H2 H 0.506972 0.202957 0.463836 0.067 Uiso 1 1 calc R U . . .
C3 C 0.6427(2) 0.17958(17) 0.34250(15) 0.0612(4) Uani 1 1 d . . . . .
C4 C 0.6190(3) 0.14311(19) 0.21218(17) 0.0713(4) Uani 1 1 d . . . . .
H4 H 0.718589 0.14006 0.188669 0.086 Uiso 1 1 calc R U . . .
C5 C 0.4463(3) 0.11153(19) 0.11819(16) 0.0746(5) Uani 1 1 d . . . . .
H5 H 0.430553 0.087486 0.030671 0.09 Uiso 1 1 calc R U . . .
C6 C 0.2956(3) 0.11441(18) 0.14974(15) 0.0681(4) Uani 1 1 d . . . . .
H6 H 0.18023 0.093637 0.084496 0.082 Uiso 1 1 calc R U . . .
C7 C 0.3274(2) 0.3939(2) -0.37994(19) 0.0754(5) Uani 1 1 d . . . . .
H7 H 0.375188 0.461689 -0.430995 0.09 Uiso 1 1 calc R U . . .
C8 C 0.3288(2) 0.45239(19) -0.26309(18) 0.0732(5) Uani 1 1 d . . . . .
H8 H 0.378715 0.557163 -0.234544 0.088 Uiso 1 1 calc R U . . .
C9 C 0.2538(2) 0.35163(18) -0.18823(15) 0.0605(4) Uani 1 1 d D . . . .
C10 C 0.1874(2) 0.19718(18) -0.23298(16) 0.0647(4) Uani 1 1 d . . . . .
H10 H 0.138762 0.126813 -0.183964 0.078 Uiso 1 1 calc R U . . .
C11 C 0.1946(2) 0.15000(19) -0.35039(16) 0.0670(4) Uani 1 1 d . . . . .
H11 H 0.150547 0.046077 -0.379601 0.08 Uiso 1 1 calc R U . . .
N2A N 0.2155(14) 0.3788(9) -0.0597(9) 0.0568(17) Uani 0.446(14) 1 d D U P A 1
N3A N 0.2643(8) 0.5119(9) -0.0154(8) 0.0599(16) Uani 0.446(14) 1 d D U P A 1
C12A C 0.2338(18) 0.5556(11) 0.1035(9) 0.0498(14) Uani 0.446(14) 1 d . U P A 1
C13A C 0.282(2) 0.7056(11) 0.1513(11) 0.0635(18) Uani 0.446(14) 1 d . U P A 1
H13A H 0.335808 0.783411 0.109823 0.076 Uiso 0.446(14) 1 calc R U P A 1
C14A C 0.245(2) 0.7353(11) 0.2640(13) 0.065(2) Uani 0.446(14) 1 d . U P A 1
H14A H 0.279502 0.836814 0.295797 0.078 Uiso 0.446(14) 1 calc R U P A 1
N4A N 0.171(2) 0.6403(13) 0.3276(11) 0.066(2) Uani 0.446(14) 1 d . U P A 1
C15A C 0.1254(19) 0.5022(12) 0.2783(11) 0.0630(18) Uani 0.446(14) 1 d . U P A 1
H15A H 0.068056 0.428363 0.321964 0.076 Uiso 0.446(14) 1 calc R U P A 1
C16A C 0.1500(15) 0.4504(8) 0.1705(10) 0.0589(18) Uani 0.446(14) 1 d . U P A 1
H16A H 0.111202 0.347021 0.142983 0.071 Uiso 0.446(14) 1 calc R U P A 1
C12B C 0.2086(13) 0.5200(8) 0.1214(7) 0.0541(15) Uani 0.554(14) 1 d DG U P A 2
C13B C 0.2794(14) 0.6778(8) 0.1471(8) 0.0642(18) Uani 0.554(14) 1 d G U P A 2
H13B H 0.337335 0.734774 0.093431 0.077 Uiso 0.554(14) 1 calc R U P A 2
C14B C 0.2637(18) 0.7506(7) 0.2531(10) 0.067(2) Uani 0.554(14) 1 d G U P A 2
H14B H 0.311092 0.856228 0.270308 0.08 Uiso 0.554(14) 1 calc R U P A 2
N4B N 0.1772(18) 0.6655(9) 0.3333(9) 0.0648(17) Uani 0.554(14) 1 d G U P A 2
C15B C 0.1063(14) 0.5076(9) 0.3076(8) 0.0628(15) Uani 0.554(14) 1 d G U P A 2
H15B H 0.048432 0.450684 0.361266 0.075 Uiso 0.554(14) 1 calc R U P A 2
C16B C 0.1221(12) 0.4349(7) 0.2016(8) 0.0619(15) Uani 0.554(14) 1 d G U P A 2
H16B H 0.074673 0.329227 0.184389 0.074 Uiso 0.554(14) 1 calc R U P A 2
C17 C 0.2306(13) 0.4596(17) 0.0169(8) 0.058(2) Uani 0.45(2) 1 d D U P A 2
C18 C 0.2541(16) 0.4161(17) -0.0779(10) 0.058(2) Uani 0.45(2) 1 d D U P A 2
N2B N 0.272(4) 0.472(4) -0.074(3) 0.062(5) Uani 0.097(12) 1 d D U P A 3
N3B N 0.193(5) 0.401(4) -0.001(3) 0.065(6) Uani 0.097(12) 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 1.3574(18) . ?
O1 H1 0.82 . ?
O2 C3 1.3579(19) . ?
O2 H2A 0.82 . ?
N1 C11 1.331(2) . ?
N1 C7 1.335(2) . ?
C1 C6 1.385(2) . ?
C1 C2 1.385(2) . ?
C2 C3 1.385(2) . ?
C2 H2 0.93 . ?
C3 C4 1.385(2) . ?
C4 C5 1.373(3) . ?
C4 H4 0.93 . ?
C5 C6 1.378(2) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.365(3) . ?
C7 H7 0.93 . ?
C8 C9 1.384(2) . ?
C8 H8 0.93 . ?
C9 C18 1.328(10) . ?
C9 C10 1.384(2) . ?
C9 N2A 1.557(10) . ?
C9 N2B 1.60(4) . ?
C10 C11 1.365(2) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
N2A N3A 1.218(11) . ?
N3A C12A 1.465(11) . ?
C12A C16A 1.369(7) . ?
C12A C13A 1.382(7) . ?
C13A C14A 1.390(8) . ?
C13A H13A 0.93 . ?
C14A N4A 1.257(9) . ?
C14A H14A 0.93 . ?
N4A C15A 1.283(8) . ?
C15A C16A 1.356(8) . ?
C15A H15A 0.93 . ?
C16A H16A 0.93 . ?
C12B C17 1.347(9) . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
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 1.193(12) . ?
N2B N3B 1.24(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 117.13(15) . . ?
O1 C1 C6 118.27(14) . . ?
O1 C1 C2 121.88(13) . . ?
C6 C1 C2 119.85(14) . . ?
C3 C2 C1 120.36(14) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
O2 C3 C2 122.09(14) . . ?
O2 C3 C4 118.05(15) . . ?
C2 C3 C4 119.86(15) . . ?
C5 C4 C3 119.05(16) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.93(15) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.94(16) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.86(16) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.21(16) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C18 C9 C10 126.4(7) . . ?
C18 C9 C8 115.0(7) . . ?
C10 C9 C8 118.61(15) . . ?
C10 C9 N2A 110.2(3) . . ?
C8 C9 N2A 131.0(3) . . ?
C10 C9 N2B 142.9(8) . . ?
C8 C9 N2B 98.4(9) . . ?
C11 C10 C9 118.76(15) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.39(15) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
N3A N2A C9 114.7(12) . . ?
N2A N3A C12A 121.2(12) . . ?
C16A C12A C13A 116.3(5) . . ?
C16A C12A N3A 122.2(6) . . ?
C13A C12A N3A 121.5(6) . . ?
C12A C13A C14A 117.1(6) . . ?
C12A C13A H13A 121.4 . . ?
C14A C13A H13A 121.4 . . ?
N4A C14A C13A 127.3(5) . . ?
N4A C14A H14A 116.4 . . ?
C13A C14A H14A 116.4 . . ?
C14A N4A C15A 113.6(6) . . ?
N4A C15A C16A 128.0(6) . . ?
N4A C15A H15A 116 . . ?
C16A C15A H15A 116 . . ?
C15A C16A C12A 117.7(5) . . ?
C15A C16A H16A 121.1 . . ?
C12A C16A H16A 121.1 . . ?
C17 C12B C13B 115.8(6) . . ?
C17 C12B C16B 124.2(6) . . ?
C13B C12B C16B 120 . . ?
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 . . ?
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 175.4(19) . . ?
C17 C18 C9 171.5(16) . . ?
N3B N2B C9 109(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 -179.55(13) . . . . ?
C6 C1 C2 C3 0.5(2) . . . . ?
C1 C2 C3 O2 178.18(14) . . . . ?
C1 C2 C3 C4 -1.4(2) . . . . ?
O2 C3 C4 C5 -178.31(15) . . . . ?
C2 C3 C4 C5 1.3(2) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
O1 C1 C6 C5 -179.43(14) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
C11 N1 C7 C8 -0.4(3) . . . . ?
N1 C7 C8 C9 -1.4(3) . . . . ?
C7 C8 C9 C18 -177.9(6) . . . . ?
C7 C8 C9 C10 2.2(2) . . . . ?
C7 C8 C9 N2A -173.1(5) . . . . ?
C7 C8 C9 N2B -175.3(12) . . . . ?
C18 C9 C10 C11 178.8(6) . . . . ?
C8 C9 C10 C11 -1.4(2) . . . . ?
N2A C9 C10 C11 174.9(4) . . . . ?
N2B C9 C10 C11 175(2) . . . . ?
C7 N1 C11 C10 1.3(2) . . . . ?
C9 C10 C11 N1 -0.4(2) . . . . ?
C10 C9 N2A N3A -177.9(6) . . . . ?
C8 C9 N2A N3A -2.2(10) . . . . ?
C9 N2A N3A C12A 178.6(7) . . . . ?
N2A N3A C12A C16A 0.1(13) . . . . ?
N2A N3A C12A C13A -177.3(9) . . . . ?
C16A C12A C13A C14A 1.8(7) . . . . ?
N3A C12A C13A C14A 179.4(11) . . . . ?
C12A C13A C14A N4A -0.7(8) . . . . ?
C13A C14A N4A C15A -0.7(7) . . . . ?
C14A N4A C15A C16A 1.2(8) . . . . ?
N4A C15A C16A C12A -0.1(8) . . . . ?
C13A C12A C16A C15A -1.5(7) . . . . ?
N3A C12A C16A C15A -179.0(10) . . . . ?
C17 C12B C13B C14B -179.9(9) . . . . ?
C16B C12B C13B C14B 0 . . . . ?
C12B C13B C14B N4B 0 . . . . ?
C13B C14B N4B C15B 0 . . . . ?
C14B N4B C15B C16B 0 . . . . ?
N4B C15B C16B C12B 0 . . . . ?
C17 C12B C16B C15B 179.9(9) . . . . ?
C13B C12B C16B C15B 0 . . . . ?
C10 C9 N2B N3B -3(4) . . . . ?
C8 C9 N2B N3B 174(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 1.95 2.7666(17) 173.5 1_556 yes
O2 H2A N4A^a 0.82 2.04 2.855(8) 174 2_666 yes
O2 H2A N4B^b 0.82 1.9 2.72(4) 177.8 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_A50_BA50_250
_database_code_depnum_ccdc_archive 'CCDC 1995709'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT077_A50_BA50_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_PLAT906_A50_BA50_250        
;
PROBLEM: Large K Value in the Analysis of Variance ......      7.421 Check 
RESPONSE: Due to diffuse scattering about the Bragg peaks.
;
# end Validation Reply Form

_audit_creation_date             2019-11-11T13:42:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C16.96 H14 N3.04 O2'
_chemical_formula_weight         292.31

#----------------------------------------------------------------------------#
#                   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                   8.10148(18)
_cell_length_b                   9.7713(2)
_cell_length_c                   10.9201(2)
_cell_angle_alpha                93.1101(18)
_cell_angle_beta                 107.2305(19)
_cell_angle_gamma                114.004(2)
_cell_volume                     738.97(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    6836
_cell_measurement_theta_min      4.283
_cell_measurement_theta_max      76.717

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

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.052
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             306
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 1 -7 0.0847
2 -1 5 0.0871
-2 -1 7 0.1232
1 -3 6 0.0981
0 -5 -1 0.0393
5 -3 -3 0.116
0 5 1 0.0131
-5 2 2 0.1027
-3 1 7 0.1163
5 -2 0 0.1098
0 -5 4 0.0805
4 2 -1 0.0622
5 -5 0 0.1116
-5 2 3 0.1092
-5 4 -1 0.1167


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

_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
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  0.46
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.848
_shelx_estimated_absorpt_T_max   0.963

#----------------------------------------------------------------------------#
#                   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      0.038699
_diffrn_orient_matrix_ub_12      -0.0591249
_diffrn_orient_matrix_ub_13      0.128415
_diffrn_orient_matrix_ub_21      -0.1225269
_diffrn_orient_matrix_ub_22      -0.165895
_diffrn_orient_matrix_ub_23      -0.077479
_diffrn_orient_matrix_ub_31      0.1811838
_diffrn_orient_matrix_ub_32      -0.0038037
_diffrn_orient_matrix_ub_33      -0.0153327
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_number            15632
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_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         4.326
_diffrn_reflns_theta_max         77.277
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.961
_reflns_Friedel_coverage         0
_reflns_number_total             3021
_reflns_number_gt                2525
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_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)+(0.0591P)²+0.1303P] 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(9)
_refine_ls_number_reflns         3021
_refine_ls_number_parameters     284
_refine_ls_number_restraints     513
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1288
_refine_ls_wR_factor_gt          0.1223
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.147
_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)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 0.52 to 0.48 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 0.16724(15) 0.15118(13) 0.30957(10) 0.0595(3) Uani 1 1 d . . . . .
H1 H 0.199081 0.174963 0.390116 0.089 Uiso 1 1 calc R U . . .
O2 O 0.81792(16) 0.21449(15) 0.43404(12) 0.0699(3) Uani 1 1 d . . . . .
H2A H 0.822906 0.251252 0.506121 0.105 Uiso 1 1 calc R U . . .
N1 N 0.26172(19) 0.24558(16) -0.42537(13) 0.0601(3) Uani 1 1 d . . . . .
C1 C 0.3180(2) 0.14969(15) 0.27992(14) 0.0486(3) Uani 1 1 d . . . . .
C2 C 0.4921(2) 0.18126(15) 0.37654(14) 0.0488(3) Uani 1 1 d . . . . .
H2 H 0.507279 0.203452 0.465153 0.059 Uiso 1 1 calc R U . . .
C3 C 0.6438(2) 0.18018(16) 0.34279(15) 0.0531(4) Uani 1 1 d . . . . .
C4 C 0.6196(3) 0.14296(18) 0.21204(16) 0.0616(4) Uani 1 1 d . . . . .
H4 H 0.720326 0.13904 0.188354 0.074 Uiso 1 1 calc R U . . .
C5 C 0.4457(3) 0.11189(19) 0.11762(16) 0.0642(4) Uani 1 1 d . . . . .
H5 H 0.429585 0.087708 0.029059 0.077 Uiso 1 1 calc R U . . .
C6 C 0.2944(2) 0.11520(17) 0.14920(15) 0.0585(4) Uani 1 1 d . . . . .
H6 H 0.177284 0.09442 0.083172 0.07 Uiso 1 1 calc R U . . .
C7 C 0.3276(2) 0.3946(2) -0.37971(18) 0.0660(4) Uani 1 1 d . . . . .
H7 H 0.376364 0.463796 -0.431146 0.079 Uiso 1 1 calc R U . . .
C8 C 0.3284(2) 0.45246(19) -0.26252(18) 0.0641(4) Uani 1 1 d . . . . .
H8 H 0.378347 0.558427 -0.233574 0.077 Uiso 1 1 calc R U . . .
C9 C 0.2533(2) 0.35027(17) -0.18752(14) 0.0528(4) Uani 1 1 d D . . . .
C10 C 0.1869(2) 0.19573(17) -0.23271(15) 0.0552(4) Uani 1 1 d . . . . .
H10 H 0.137408 0.123951 -0.183354 0.066 Uiso 1 1 calc R U . . .
C11 C 0.1947(2) 0.14916(18) -0.35055(15) 0.0575(4) Uani 1 1 d . . . . .
H11 H 0.150577 0.044088 -0.380213 0.069 Uiso 1 1 calc R U . . .
N2A N 0.2133(14) 0.3786(9) -0.0597(8) 0.0483(16) Uani 0.451(13) 1 d D U P A 1
N3A N 0.2648(7) 0.5132(8) -0.0169(8) 0.0502(14) Uani 0.451(13) 1 d D U P A 1
C12A C 0.2315(16) 0.5542(10) 0.0999(9) 0.0429(13) Uani 0.451(13) 1 d . U P A 1
C13A C 0.2813(19) 0.7056(10) 0.1478(10) 0.0542(17) Uani 0.451(13) 1 d . U P A 1
H13A H 0.335397 0.784166 0.105168 0.065 Uiso 0.451(13) 1 calc R U P A 1
C14A C 0.248(2) 0.7358(11) 0.2616(12) 0.056(2) Uani 0.451(13) 1 d . U P A 1
H14A H 0.283973 0.838793 0.294027 0.067 Uiso 0.451(13) 1 calc R U P A 1
N4A N 0.174(2) 0.6401(12) 0.3264(10) 0.0530(15) Uani 0.451(13) 1 d . U P A 1
C15A C 0.1260(15) 0.5007(10) 0.2780(9) 0.0506(15) Uani 0.451(13) 1 d . U P A 1
H15A H 0.069386 0.426429 0.323209 0.061 Uiso 0.451(13) 1 calc R U P A 1
C16A C 0.1484(13) 0.4483(8) 0.1682(9) 0.0485(15) Uani 0.451(13) 1 d . U P A 1
H16A H 0.108502 0.343524 0.140376 0.058 Uiso 0.451(13) 1 calc R U P A 1
C12B C 0.2119(12) 0.5243(8) 0.1243(6) 0.0455(14) Uani 0.549(13) 1 d DG U P A 2
C13B C 0.2813(15) 0.6823(8) 0.1500(8) 0.0557(17) Uani 0.549(13) 1 d G U P A 2
H13B H 0.341139 0.740898 0.096459 0.067 Uiso 0.549(13) 1 calc R U P A 2
C14B C 0.2621(18) 0.7538(6) 0.2550(10) 0.0564(19) Uani 0.549(13) 1 d G U P A 2
H14B H 0.309027 0.860635 0.272426 0.068 Uiso 0.549(13) 1 calc R U P A 2
N4B N 0.1736(17) 0.6672(9) 0.3343(8) 0.0560(15) Uani 0.549(13) 1 d G U P A 2
C15B C 0.1043(12) 0.5092(8) 0.3085(7) 0.0525(13) Uani 0.549(13) 1 d G U P A 2
H15B H 0.044446 0.450643 0.362128 0.063 Uiso 0.549(13) 1 calc R U P A 2
C16B C 0.1234(10) 0.4378(6) 0.2036(7) 0.0517(14) Uani 0.549(13) 1 d G U P A 2
H16B H 0.076556 0.330903 0.186162 0.062 Uiso 0.549(13) 1 calc R U P A 2
C17 C 0.2326(11) 0.4614(14) 0.0173(6) 0.0490(18) Uani 0.48(2) 1 d D U P A 2
C18 C 0.2536(15) 0.4139(14) -0.0773(9) 0.051(2) Uani 0.48(2) 1 d D U P A 2
N2B N 0.277(5) 0.474(5) -0.072(4) 0.053(5) Uani 0.068(10) 1 d D U P A 3
N3B N 0.195(6) 0.397(6) -0.003(4) 0.060(7) Uani 0.068(10) 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 1.3585(18) . ?
O1 H1 0.83 . ?
O2 C3 1.3571(18) . ?
O2 H2A 0.83 . ?
N1 C11 1.334(2) . ?
N1 C7 1.336(2) . ?
C1 C6 1.386(2) . ?
C1 C2 1.388(2) . ?
C2 C3 1.387(2) . ?
C2 H2 0.94 . ?
C3 C4 1.389(2) . ?
C4 C5 1.378(2) . ?
C4 H4 0.94 . ?
C5 C6 1.379(2) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.368(3) . ?
C7 H7 0.94 . ?
C8 C9 1.388(2) . ?
C8 H8 0.94 . ?
C9 C18 1.323(9) . ?
C9 C10 1.384(2) . ?
C9 N2A 1.558(9) . ?
C9 N2B 1.61(5) . ?
C10 C11 1.369(2) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
N2A N3A 1.222(10) . ?
N3A C12A 1.447(9) . ?
C12A C16A 1.377(6) . ?
C12A C13A 1.390(7) . ?
C13A C14A 1.390(7) . ?
C13A H13A 0.94 . ?
C14A N4A 1.266(8) . ?
C14A H14A 0.94 . ?
N4A C15A 1.288(8) . ?
C15A C16A 1.367(7) . ?
C15A H15A 0.94 . ?
C16A H16A 0.94 . ?
C12B C17 1.376(7) . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
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 1.194(11) . ?
N2B N3B 1.24(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 117.26(14) . . ?
O1 C1 C6 118.24(13) . . ?
O1 C1 C2 121.72(13) . . ?
C6 C1 C2 120.04(14) . . ?
C3 C2 C1 120.23(13) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
O2 C3 C2 122.08(13) . . ?
O2 C3 C4 118.02(14) . . ?
C2 C3 C4 119.90(14) . . ?
C5 C4 C3 118.95(15) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.95(15) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.90(15) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C8 123.85(15) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.15(15) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C18 C9 C10 126.5(6) . . ?
C18 C9 C8 114.9(6) . . ?
C10 C9 C8 118.62(15) . . ?
C10 C9 N2A 111.1(3) . . ?
C8 C9 N2A 130.1(3) . . ?
C10 C9 N2B 144.2(10) . . ?
C8 C9 N2B 97.2(10) . . ?
C11 C10 C9 118.86(14) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.23(15) . . ?
N1 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
N3A N2A C9 114.0(11) . . ?
N2A N3A C12A 119.3(11) . . ?
C16A C12A C13A 116.5(5) . . ?
C16A C12A N3A 123.0(5) . . ?
C13A C12A N3A 120.6(6) . . ?
C14A C13A C12A 117.0(6) . . ?
C14A C13A H13A 121.5 . . ?
C12A C13A H13A 121.5 . . ?
N4A C14A C13A 127.3(6) . . ?
N4A C14A H14A 116.4 . . ?
C13A C14A H14A 116.4 . . ?
C14A N4A C15A 114.0(5) . . ?
N4A C15A C16A 127.4(5) . . ?
N4A C15A H15A 116.3 . . ?
C16A C15A H15A 116.3 . . ?
C15A C16A C12A 117.7(4) . . ?
C15A C16A H16A 121.1 . . ?
C12A C16A H16A 121.1 . . ?
C17 C12B C13B 116.7(6) . . ?
C17 C12B C16B 123.2(6) . . ?
C13B C12B C16B 120 . . ?
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 . . ?
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 176.7(16) . . ?
C17 C18 C9 172.8(12) . . ?
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 -179.39(12) . . . . ?
C6 C1 C2 C3 0.7(2) . . . . ?
C1 C2 C3 O2 178.17(13) . . . . ?
C1 C2 C3 C4 -1.9(2) . . . . ?
O2 C3 C4 C5 -178.22(14) . . . . ?
C2 C3 C4 C5 1.8(2) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
O1 C1 C6 C5 -179.42(13) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
C11 N1 C7 C8 -0.6(2) . . . . ?
N1 C7 C8 C9 -1.1(2) . . . . ?
C7 C8 C9 C18 -178.1(5) . . . . ?
C7 C8 C9 C10 2.0(2) . . . . ?
C7 C8 C9 N2A -172.4(5) . . . . ?
C7 C8 C9 N2B -176.7(14) . . . . ?
C18 C9 C10 C11 179.0(6) . . . . ?
C8 C9 C10 C11 -1.1(2) . . . . ?
N2A C9 C10 C11 174.3(4) . . . . ?
N2B C9 C10 C11 177(2) . . . . ?
C7 N1 C11 C10 1.5(2) . . . . ?
C9 C10 C11 N1 -0.6(2) . . . . ?
C10 C9 N2A N3A -178.3(6) . . . . ?
C8 C9 N2A N3A -3.6(10) . . . . ?
C9 N2A N3A C12A 178.6(6) . . . . ?
N2A N3A C12A C16A 1.9(12) . . . . ?
N2A N3A C12A C13A -177.4(8) . . . . ?
C16A C12A C13A C14A 1.8(6) . . . . ?
N3A C12A C13A C14A -178.9(9) . . . . ?
C12A C13A C14A N4A -1.1(7) . . . . ?
C13A C14A N4A C15A -0.2(7) . . . . ?
C14A N4A C15A C16A 0.6(7) . . . . ?
N4A C15A C16A C12A 0.2(7) . . . . ?
C13A C12A C16A C15A -1.4(6) . . . . ?
N3A C12A C16A C15A 179.3(9) . . . . ?
C17 C12B C13B C14B 178.8(7) . . . . ?
C16B C12B C13B C14B 0 . . . . ?
C12B C13B C14B N4B 0 . . . . ?
C13B C14B N4B C15B 0 . . . . ?
C14B N4B C15B C16B 0 . . . . ?
N4B C15B C16B C12B 0 . . . . ?
C17 C12B C16B C15B -178.7(8) . . . . ?
C13B C12B C16B C15B 0 . . . . ?
C10 C9 N2B N3B -5(5) . . . . ?
C8 C9 N2B N3B 173(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 1.94 2.7638(17) 173.9 1_556 yes
O2 H2A N4A^a 0.83 2.05 2.877(8) 173.4 2_666 yes
O2 H2A N4B^b 0.83 1.86 2.69(4) 178.3 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_A50_BA50_190
_database_code_depnum_ccdc_archive 'CCDC 1995706'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT906_A50_BA50_190        
;
PROBLEM: Large K Value in the Analysis of Variance ......      5.196 Check 
RESPONSE: Due to diffuse scattering about the Bragg peaks.
;
# end Validation Reply Form

_audit_creation_date             2019-11-11T13:37:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C16.97 H14 N3.01 O2'
_chemical_formula_weight         292.19

#----------------------------------------------------------------------------#
#                   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                   8.0587(2)
_cell_length_b                   9.7436(3)
_cell_length_c                   10.9027(2)
_cell_angle_alpha                92.797(2)
_cell_angle_beta                 107.379(2)
_cell_angle_gamma                114.108(3)
_cell_volume                     731.27(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    7786
_cell_measurement_theta_min      4.31
_cell_measurement_theta_max      76.755

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

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.052
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             306
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 0 -7 0.0847
5 -3 -3 0.116
1 -2 6 0.0981
-2 0 7 0.1232
-5 2 3 0.1092
-5 3 -2 0.1167
0 -5 -1 0.0393
0 5 1 0.0131
2 0 5 0.0871
-3 2 7 0.1163
5 -2 0 0.1098
0 -5 4 0.0805
5 -5 0 0.1116
4 2 -2 0.0622
-5 1 3 0.1027


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

_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
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  0.46
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.847
_shelx_estimated_absorpt_T_max   0.963

#----------------------------------------------------------------------------#
#                   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      0.051444
_diffrn_orient_matrix_ub_12      -0.0431291
_diffrn_orient_matrix_ub_13      0.1356796
_diffrn_orient_matrix_ub_21      -0.1180049
_diffrn_orient_matrix_ub_22      -0.1712814
_diffrn_orient_matrix_ub_23      -0.0644681
_diffrn_orient_matrix_ub_31      0.1827398
_diffrn_orient_matrix_ub_32      -0.0025709
_diffrn_orient_matrix_ub_33      -0.0152772
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.051
_diffrn_reflns_number            15546
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_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         4.333
_diffrn_reflns_theta_max         77.164
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_reflns_Friedel_coverage         0
_reflns_number_total             2987
_reflns_number_gt                2614
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_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)+(0.0537P)²+0.1678P] 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       0.0044(8)
_refine_ls_number_reflns         2987
_refine_ls_number_parameters     284
_refine_ls_number_restraints     513
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.043
_refine_ls_wR_factor_ref         0.1205
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.15
_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)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 0.51 to 0.49 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 0.16575(14) 0.15308(12) 0.30941(10) 0.0470(3) Uani 1 1 d . . . . .
H1 H 0.19786 0.175948 0.391092 0.07 Uiso 1 1 calc R U . . .
O2 O 0.82035(15) 0.21461(14) 0.43492(11) 0.0547(3) Uani 1 1 d . . . . .
H2A H 0.825987 0.252889 0.507639 0.082 Uiso 1 1 calc R U . . .
N1 N 0.26204(18) 0.24630(15) -0.42555(12) 0.0485(3) Uani 1 1 d . . . . .
C1 C 0.3169(2) 0.15094(14) 0.27981(13) 0.0387(3) Uani 1 1 d . . . . .
C2 C 0.4925(2) 0.18234(14) 0.37687(13) 0.0389(3) Uani 1 1 d . . . . .
H2 H 0.508214 0.205132 0.466518 0.047 Uiso 1 1 calc R U . . .
C3 C 0.6450(2) 0.18050(15) 0.34317(14) 0.0420(3) Uani 1 1 d . . . . .
C4 C 0.6207(2) 0.14303(17) 0.21215(15) 0.0487(4) Uani 1 1 d . . . . .
H4 H 0.722923 0.138683 0.188411 0.058 Uiso 1 1 calc R U . . .
C5 C 0.4450(2) 0.11219(17) 0.11697(15) 0.0508(4) Uani 1 1 d . . . . .
H5 H 0.428529 0.087577 0.027394 0.061 Uiso 1 1 calc R U . . .
C6 C 0.2928(2) 0.11617(16) 0.14850(14) 0.0468(4) Uani 1 1 d . . . . .
H6 H 0.173769 0.095511 0.08159 0.056 Uiso 1 1 calc R U . . .
C7 C 0.3281(2) 0.39586(19) -0.37922(17) 0.0545(4) Uani 1 1 d . . . . .
H7 H 0.377781 0.46686 -0.430882 0.065 Uiso 1 1 calc R U . . .
C8 C 0.3282(2) 0.45232(17) -0.26131(17) 0.0535(4) Uani 1 1 d . . . . .
H8 H 0.378768 0.559537 -0.231636 0.064 Uiso 1 1 calc R U . . .
C9 C 0.2526(2) 0.34903(16) -0.18662(14) 0.0428(3) Uani 1 1 d D . . . .
C10 C 0.1862(2) 0.19376(16) -0.23222(14) 0.0433(3) Uani 1 1 d . . . . .
H10 H 0.135917 0.120283 -0.182529 0.052 Uiso 1 1 calc R U . . .
C11 C 0.1948(2) 0.14849(17) -0.35069(14) 0.0450(3) Uani 1 1 d . . . . .
H11 H 0.150602 0.04224 -0.380895 0.054 Uiso 1 1 calc R U . . .
N2A N 0.2159(15) 0.3786(9) -0.0590(8) 0.0413(16) Uani 0.481(13) 1 d D U P A 1
N3A N 0.2661(6) 0.5139(7) -0.0175(7) 0.0399(13) Uani 0.481(13) 1 d D U P A 1
C12A C 0.2293(12) 0.5510(8) 0.0973(7) 0.0336(11) Uani 0.481(13) 1 d . U P A 1
C13A C 0.2810(17) 0.7045(9) 0.1439(9) 0.0420(15) Uani 0.481(13) 1 d . U P A 1
H13A H 0.336727 0.78291 0.099685 0.05 Uiso 0.481(13) 1 calc R U P A 1
C14A C 0.248(2) 0.7376(10) 0.2562(12) 0.0440(18) Uani 0.481(13) 1 d . U P A 1
H14A H 0.28547 0.842404 0.287253 0.053 Uiso 0.481(13) 1 calc R U P A 1
N4A N 0.1725(17) 0.6417(10) 0.3234(9) 0.0406(12) Uani 0.481(13) 1 d . U P A 1
C15A C 0.1237(11) 0.4997(8) 0.2773(8) 0.0376(13) Uani 0.481(13) 1 d . U P A 1
H15A H 0.066421 0.425397 0.32423 0.045 Uiso 0.481(13) 1 calc R U P A 1
C16A C 0.1469(11) 0.4465(7) 0.1673(8) 0.0381(13) Uani 0.481(13) 1 d . U P A 1
H16A H 0.106866 0.34029 0.14045 0.046 Uiso 0.481(13) 1 calc R U P A 1
C12B C 0.2149(11) 0.5299(8) 0.1275(6) 0.0354(13) Uani 0.519(13) 1 d DG U P A 2
C13B C 0.2846(15) 0.6883(8) 0.1545(9) 0.0454(18) Uani 0.519(13) 1 d G U P A 2
H13B H 0.346627 0.748953 0.101194 0.054 Uiso 0.519(13) 1 calc R U P A 2
C14B C 0.2635(18) 0.7578(6) 0.2594(10) 0.0424(18) Uani 0.519(13) 1 d G U P A 2
H14B H 0.3111 0.866076 0.277847 0.051 Uiso 0.519(13) 1 calc R U P A 2
N4B N 0.1727(16) 0.6690(8) 0.3374(9) 0.0437(14) Uani 0.519(13) 1 d G U P A 2
C15B C 0.1030(10) 0.5107(8) 0.3104(7) 0.0405(12) Uani 0.519(13) 1 d G U P A 2
H15B H 0.040976 0.449996 0.363642 0.049 Uiso 0.519(13) 1 calc R U P A 2
C16B C 0.1241(9) 0.4411(6) 0.2054(7) 0.0387(13) Uani 0.519(13) 1 d G U P A 2
H16B H 0.076501 0.33287 0.186988 0.046 Uiso 0.519(13) 1 calc R U P A 2
C17 C 0.2336(8) 0.4630(10) 0.0184(6) 0.0392(14) Uani 0.487(17) 1 d D U P A 2
C18 C 0.2498(17) 0.4130(12) -0.0766(9) 0.0443(19) Uani 0.487(17) 1 d D U P A 2
N2B N 0.289(9) 0.492(11) -0.061(9) 0.049(6) Uani 0.026(6) 1 d D U P A 3
N3B N 0.171(9) 0.392(11) -0.023(10) 0.047(9) Uani 0.026(6) 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 1.3578(17) . ?
O1 H1 0.84 . ?
O2 C3 1.3591(17) . ?
O2 H2A 0.84 . ?
N1 C11 1.3366(19) . ?
N1 C7 1.340(2) . ?
C1 C6 1.391(2) . ?
C1 C2 1.3912(19) . ?
C2 C3 1.391(2) . ?
C2 H2 0.95 . ?
C3 C4 1.391(2) . ?
C4 C5 1.384(2) . ?
C4 H4 0.95 . ?
C5 C6 1.384(2) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.373(2) . ?
C7 H7 0.95 . ?
C8 C9 1.387(2) . ?
C8 H8 0.95 . ?
C9 C18 1.335(10) . ?
C9 C10 1.3888(19) . ?
C9 N2A 1.544(9) . ?
C9 N2B 1.78(13) . ?
C10 C11 1.375(2) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
N2A N3A 1.226(9) . ?
N3A C12A 1.431(8) . ?
C12A C16A 1.374(6) . ?
C12A C13A 1.399(6) . ?
C13A C14A 1.379(6) . ?
C13A H13A 0.95 . ?
C14A N4A 1.284(7) . ?
C14A H14A 0.95 . ?
N4A C15A 1.301(7) . ?
C15A C16A 1.377(5) . ?
C15A H15A 0.95 . ?
C16A H16A 0.95 . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
C12B C17 1.405(6) . ?
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 1.188(11) . ?
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 117.17(13) . . ?
O1 C1 C6 118.27(13) . . ?
O1 C1 C2 121.70(12) . . ?
C6 C1 C2 120.03(13) . . ?
C3 C2 C1 120.25(13) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
O2 C3 C2 122.00(13) . . ?
O2 C3 C4 117.99(13) . . ?
C2 C3 C4 120.01(13) . . ?
C5 C4 C3 118.89(14) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C6 C5 C4 121.91(14) . . ?
C6 C5 H5 119 . . ?
C4 C5 H5 119 . . ?
C5 C6 C1 118.88(14) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C8 123.73(14) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.38(14) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C18 C9 C8 114.5(5) . . ?
C18 C9 C10 126.9(5) . . ?
C8 C9 C10 118.63(14) . . ?
C8 C9 N2A 129.3(3) . . ?
C10 C9 N2A 112.0(3) . . ?
C8 C9 N2B 94(2) . . ?
C10 C9 N2B 147(2) . . ?
C11 C10 C9 118.70(14) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
N1 C11 C10 123.36(14) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
N3A N2A C9 114.3(10) . . ?
N2A N3A C12A 118.0(10) . . ?
C16A C12A C13A 116.5(4) . . ?
C16A C12A N3A 124.9(5) . . ?
C13A C12A N3A 118.7(6) . . ?
C14A C13A C12A 117.5(5) . . ?
C14A C13A H13A 121.2 . . ?
C12A C13A H13A 121.2 . . ?
N4A C14A C13A 126.9(6) . . ?
N4A C14A H14A 116.6 . . ?
C13A C14A H14A 116.6 . . ?
C14A N4A C15A 114.4(5) . . ?
N4A C15A C16A 126.4(4) . . ?
N4A C15A H15A 116.8 . . ?
C16A C15A H15A 116.8 . . ?
C12A C16A C15A 118.3(4) . . ?
C12A C16A H16A 120.8 . . ?
C15A C16A H16A 120.8 . . ?
C13B C12B C16B 120 . . ?
C13B C12B C17 118.5(5) . . ?
C16B C12B C17 121.5(5) . . ?
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 176.6(11) . . ?
C17 C18 C9 175.3(12) . . ?
N3B N2B C9 89(10) . . ?

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 -179.44(12) . . . . ?
C6 C1 C2 C3 0.58(19) . . . . ?
C1 C2 C3 O2 178.18(12) . . . . ?
C1 C2 C3 C4 -1.8(2) . . . . ?
O2 C3 C4 C5 -178.18(13) . . . . ?
C2 C3 C4 C5 1.8(2) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
O1 C1 C6 C5 -179.41(12) . . . . ?
C2 C1 C6 C5 0.6(2) . . . . ?
C11 N1 C7 C8 -0.7(2) . . . . ?
N1 C7 C8 C9 -1.2(2) . . . . ?
C7 C8 C9 C18 -177.0(6) . . . . ?
C7 C8 C9 C10 2.1(2) . . . . ?
C7 C8 C9 N2A -173.2(5) . . . . ?
C7 C8 C9 N2B -178(2) . . . . ?
C18 C9 C10 C11 177.7(7) . . . . ?
C8 C9 C10 C11 -1.2(2) . . . . ?
N2A C9 C10 C11 174.9(4) . . . . ?
N2B C9 C10 C11 179(4) . . . . ?
C7 N1 C11 C10 1.7(2) . . . . ?
C9 C10 C11 N1 -0.7(2) . . . . ?
C8 C9 N2A N3A -2.0(10) . . . . ?
C10 C9 N2A N3A -177.6(6) . . . . ?
C9 N2A N3A C12A 177.3(6) . . . . ?
N2A N3A C12A C16A 2.1(10) . . . . ?
N2A N3A C12A C13A -178.3(7) . . . . ?
C16A C12A C13A C14A 1.1(6) . . . . ?
N3A C12A C13A C14A -178.6(7) . . . . ?
C12A C13A C14A N4A -0.7(7) . . . . ?
C13A C14A N4A C15A 0.0(6) . . . . ?
C14A N4A C15A C16A 0.4(6) . . . . ?
C13A C12A C16A C15A -0.8(5) . . . . ?
N3A C12A C16A C15A 178.8(7) . . . . ?
N4A C15A C16A C12A 0.0(6) . . . . ?
C16B C12B C13B C14B 0 . . . . ?
C17 C12B C13B C14B 178.1(6) . . . . ?
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 -178.1(6) . . . . ?
C8 C9 N2B N3B 162(5) . . . . ?
C10 C9 N2B N3B -18(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 2.7579(16) 173.5 1_556 yes
O2 H2A N4A^a 0.84 2.06 2.896(8) 174.7 2_666 yes
O2 H2A N4B^b 0.84 1.81 2.65(4) 177.6 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_BE75_BA25_290
_database_code_depnum_ccdc_archive 'CCDC 1995704'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT911_BE75_BA25_290       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          4 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2020-04-01T11:40:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C18.02 H15.52 N2 O2'
_chemical_formula_weight         292.05

#----------------------------------------------------------------------------#
#                   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                   8.18898(10)
_cell_length_b                   9.90985(17)
_cell_length_c                   10.91962(12)
_cell_angle_alpha                92.9620(16)
_cell_angle_beta                 107.4781(11)
_cell_angle_gamma                114.2775(13)
_cell_volume                     754.69(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    16387
_cell_measurement_theta_min      4.322
_cell_measurement_theta_max      76.808

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

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.066
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             307
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -6 0 0.0556
-1 5 3 0.0598
1 1 -7 0.0688
-2 6 0 0.0503
2 5 -1 0.0374
-5 1 1 0.0337
5 -1 -1 0.0318
-1 5 -5 0.0636
-3 0 -4 0.0609
2 -2 5 0.0662
2 3 2 0.0477
5 -2 -4 0.0659
-2 -3 -2 0.0622
1 -5 4 0.0717
2 2 3 0.0581
-4 5 -2 0.0542
5 -5 0 0.0498
0 -3 6 0.0788


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

_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.92863
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.956

#----------------------------------------------------------------------------#
#                   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      -0.0095312
_diffrn_orient_matrix_ub_12      -0.1049525
_diffrn_orient_matrix_ub_13      -0.1138171
_diffrn_orient_matrix_ub_21      -0.2202801
_diffrn_orient_matrix_ub_22      -0.0777899
_diffrn_orient_matrix_ub_23      -0.0452948
_diffrn_orient_matrix_ub_31      -0.0080418
_diffrn_orient_matrix_ub_32      0.1150876
_diffrn_orient_matrix_ub_33      -0.088318
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_number            27967
_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       13
_diffrn_reflns_theta_min         4.334
_diffrn_reflns_theta_max         77.441
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.964
_reflns_Friedel_coverage         0
_reflns_number_total             3101
_reflns_number_gt                2708
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_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)+(0.0562P)²+0.0549P] 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(9)
_refine_ls_number_reflns         3101
_refine_ls_number_parameters     284
_refine_ls_number_restraints     579
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.1068
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.03

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

_refine_special_details          
;
 To help model the substitution of the bis(4-pyridyl)acetylene with 
 1,2-bis(4-pyridyl)ethylene, the atom sites N2 and  C12 < C18, were split into
 parts A and B. The site associated with the rings were allowed to free refine
 their site occupancies to a total value of 1.0, while the C12 and C13 sites 
 were constrained to 0.75 and C19 and C20 (acetyl moiety) were constrained to
 0.25. To help maintain reasonable ADP and bond lengths, SIMU, RIGU, and DFIX 
 restraints and constraints were applied. At this temperature the ratio of the
 disordered BPE sites (A and B) were 0.66 and 0.09, 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 0.16838(11) 0.15027(10) 0.30475(7) 0.0628(2) Uani 1 1 d . . . . .
H1 H 0.199966 0.175064 0.384292 0.094 Uiso 1 1 calc R U . . .
O2 O 0.81848(12) 0.22485(11) 0.43083(8) 0.0718(3) Uani 1 1 d . . . . .
H2A H 0.822539 0.259877 0.501989 0.108 Uiso 1 1 calc R U . . .
N1 N 0.26147(14) 0.24395(12) -0.43155(9) 0.0623(3) Uani 1 1 d . . . . .
C1 C 0.31811(15) 0.14894(11) 0.27610(10) 0.0501(2) Uani 1 1 d . . . . .
C2 C 0.49312(15) 0.18643(11) 0.37246(9) 0.0506(2) Uani 1 1 d . . . . .
H2 H 0.509784 0.212309 0.459958 0.061 Uiso 1 1 calc R U . . .
C3 C 0.64419(16) 0.18577(12) 0.33970(10) 0.0539(3) Uani 1 1 d . . . . .
C4 C 0.61819(18) 0.14435(13) 0.20866(11) 0.0620(3) Uani 1 1 d . . . . .
H4 H 0.717585 0.142036 0.185543 0.074 Uiso 1 1 calc R U . . .
C5 C 0.4433(2) 0.10701(13) 0.11427(11) 0.0652(3) Uani 1 1 d . . . . .
H5 H 0.426022 0.080164 0.026795 0.078 Uiso 1 1 calc R U . . .
C6 C 0.29238(18) 0.10815(12) 0.14540(10) 0.0597(3) Uani 1 1 d . . . . .
H6 H 0.175113 0.081992 0.079856 0.072 Uiso 1 1 calc R U . . .
C7 C 0.19670(17) 0.14813(14) -0.35709(11) 0.0623(3) Uani 1 1 d . . . . .
H7 H 0.155474 0.045813 -0.386481 0.075 Uiso 1 1 calc R U . . .
C8 C 0.18751(17) 0.19240(13) -0.23906(11) 0.0594(3) Uani 1 1 d . . . . .
H8 H 0.140414 0.120745 -0.190887 0.071 Uiso 1 1 calc R U . . .
C9 C 0.24833(15) 0.34348(13) -0.19202(10) 0.0534(3) Uani 1 1 d D U . . .
C10 C 0.32143(17) 0.44464(13) -0.26702(12) 0.0613(3) Uani 1 1 d . . . . .
H10 H 0.36852 0.547929 -0.238135 0.074 Uiso 1 1 calc R U . . .
C11 C 0.32344(17) 0.39035(15) -0.38462(12) 0.0643(3) Uani 1 1 d . . . . .
H11 H 0.370732 0.459589 -0.434543 0.077 Uiso 1 1 calc R U . . .
C12A C 0.2183(6) 0.3777(3) -0.0675(3) 0.0470(6) Uani 0.666(7) 1 d D U P A 1
H12A H 0.164252 0.298171 -0.028082 0.056 Uiso 0.666(7) 1 calc R U P A 1
C13A C 0.2659(3) 0.5178(3) -0.0107(2) 0.0455(5) Uani 0.666(7) 1 d D U P A 1
H13A H 0.323971 0.595875 -0.050158 0.055 Uiso 0.666(7) 1 calc R U P A 1
C12B C 0.274(4) 0.458(2) -0.083(2) 0.057(3) Uani 0.093(7) 1 d D U P A 2
H12B H 0.348125 0.559951 -0.078042 0.069 Uiso 0.093(7) 1 calc R U P A 2
C13B C 0.197(3) 0.418(2) 0.004(2) 0.058(3) Uani 0.093(7) 1 d D U P A 2
H13B H 0.125415 0.314272 -0.003902 0.069 Uiso 0.093(7) 1 calc R U P A 2
C14A C 0.2342(7) 0.5607(4) 0.1105(4) 0.0422(8) Uani 0.666(7) 1 d DG U P A 1
C15A C 0.1505(8) 0.4533(3) 0.1781(4) 0.0510(9) Uani 0.666(7) 1 d G U P A 1
H15A H 0.114518 0.35188 0.149087 0.061 Uiso 0.666(7) 1 calc R U P A 1
C16A C 0.1204(8) 0.4975(4) 0.2890(4) 0.0517(10) Uani 0.666(7) 1 d G U P A 1
H16A H 0.064397 0.425681 0.334215 0.062 Uiso 0.666(7) 1 calc R U P A 1
N2A N 0.1742(8) 0.6491(5) 0.3324(4) 0.0530(11) Uani 0.666(7) 1 d G U P A 1
C17A C 0.2580(8) 0.7565(3) 0.2648(4) 0.0536(8) Uani 0.666(7) 1 d G U P A 1
H17A H 0.293918 0.857898 0.29379 0.064 Uiso 0.666(7) 1 calc R U P A 1
C18A C 0.2880(7) 0.7123(4) 0.1539(4) 0.0503(8) Uani 0.666(7) 1 d G U P A 1
H18A H 0.344041 0.7841 0.108662 0.06 Uiso 0.666(7) 1 calc R U P A 1
C14B C 0.2098(16) 0.5174(11) 0.1170(9) 0.0551(18) Uani 0.334(7) 1 d D U P A 2
C15B C 0.1287(18) 0.4447(9) 0.2028(11) 0.0586(17) Uani 0.334(7) 1 d . U P A 2
H15B H 0.078015 0.340141 0.19203 0.07 Uiso 0.334(7) 1 calc R U P A 2
C16B C 0.1232(18) 0.5275(12) 0.3042(10) 0.0533(15) Uani 0.334(7) 1 d . U P A 2
H16B H 0.064776 0.469486 0.356941 0.064 Uiso 0.334(7) 1 calc R U P A 2
N2B N 0.1796(19) 0.6616(11) 0.3384(10) 0.065(2) Uani 0.334(7) 1 d . U P A 2
C17B C 0.2520(17) 0.7234(11) 0.2601(11) 0.0591(16) Uani 0.334(7) 1 d . U P A 2
H17B H 0.302414 0.828115 0.278865 0.071 Uiso 0.334(7) 1 calc R U P A 2
C18B C 0.2732(14) 0.6693(10) 0.1515(9) 0.0547(16) Uani 0.334(7) 1 d . U P A 2
H18B H 0.329604 0.734598 0.101985 0.066 Uiso 0.334(7) 1 calc R U P A 2
C19 C 0.250(2) 0.4138(18) -0.0781(13) 0.066(2) Uani 0.25 1 d D U P A 2
C20 C 0.2380(18) 0.4642(19) 0.0122(10) 0.072(2) Uani 0.25 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   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(13) . ?
O1 H1 0.82 . ?
O2 C3 1.3527(14) . ?
O2 H2A 0.82 . ?
N1 C7 1.3300(16) . ?
N1 C11 1.3366(16) . ?
C1 C2 1.3839(15) . ?
C1 C6 1.3909(14) . ?
C2 C3 1.3894(15) . ?
C2 H2 0.93 . ?
C3 C4 1.3949(14) . ?
C4 C5 1.3745(18) . ?
C4 H4 0.93 . ?
C5 C6 1.3804(17) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.3734(15) . ?
C7 H7 0.93 . ?
C8 C9 1.3810(16) . ?
C8 H8 0.93 . ?
C9 C10 1.3856(17) . ?
C9 C19 1.389(11) . ?
C9 C12A 1.499(3) . ?
C9 C12B 1.503(17) . ?
C10 C11 1.3737(16) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12A C13A 1.336(4) . ?
C12A H12A 0.93 . ?
C13A C14A 1.496(3) . ?
C13A H13A 0.93 . ?
C12B C13B 1.288(18) . ?
C12B H12B 0.93 . ?
C13B C14B 1.489(17) . ?
C13B H13B 0.93 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.93 . ?
C16A N2A 1.39 . ?
C16A H16A 0.93 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.93 . ?
C18A H18A 0.93 . ?
C14B C20 1.356(11) . ?
C14B C18B 1.363(8) . ?
C14B C15B 1.374(8) . ?
C15B C16B 1.366(8) . ?
C15B H15B 0.93 . ?
C16B N2B 1.207(8) . ?
C16B C17B 1.957(12) . ?
C16B H16B 0.93 . ?
N2B C17B 1.232(7) . ?
C17B C18B 1.363(7) . ?
C17B H17B 0.93 . ?
C18B H18B 0.93 . ?
C19 C20 1.129(14) . ?

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 . . ?
C7 N1 C11 116.51(9) . . ?
O1 C1 C2 122.06(9) . . ?
O1 C1 C6 118.26(10) . . ?
C2 C1 C6 119.68(10) . . ?
C1 C2 C3 120.62(9) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O2 C3 C2 122.33(9) . . ?
O2 C3 C4 117.98(10) . . ?
C2 C3 C4 119.69(10) . . ?
C5 C4 C3 118.91(11) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.98(10) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.11(11) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N1 C7 C8 123.43(11) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.89(11) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C10 117.09(10) . . ?
C8 C9 C19 130.1(7) . . ?
C10 C9 C19 112.8(7) . . ?
C8 C9 C12A 115.36(14) . . ?
C10 C9 C12A 127.48(14) . . ?
C8 C9 C12B 145.8(6) . . ?
C10 C9 C12B 97.1(6) . . ?
C19 C9 C12B 15.8(5) . . ?
C11 C10 C9 119.13(11) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C11 C10 123.90(11) . . ?
N1 C11 H11 118 . . ?
C10 C11 H11 118 . . ?
C13A C12A C9 122.7(3) . . ?
C13A C12A H12A 118.6 . . ?
C9 C12A H12A 118.6 . . ?
C12A C13A C14A 125.9(2) . . ?
C12A C13A H13A 117 . . ?
C14A C13A H13A 117 . . ?
C13B C12B C9 121.5(19) . . ?
C13B C12B H12B 119.2 . . ?
C9 C12B H12B 119.2 . . ?
C12B C13B C14B 127.4(18) . . ?
C12B C13B H13B 116.3 . . ?
C14B C13B H13B 116.3 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13A 121.8(2) . . ?
C18A C14A C13A 118.2(2) . . ?
C14A C15A C16A 120 . . ?
C14A C15A H15A 120 . . ?
C16A C15A H15A 120 . . ?
N2A C16A C15A 120 . . ?
N2A C16A H16A 120 . . ?
C15A C16A H16A 120 . . ?
C17A N2A C16A 120 . . ?
N2A C17A C18A 120 . . ?
N2A C17A H17A 120 . . ?
C18A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C20 C14B C18B 118.6(9) . . ?
C20 C14B C15B 131.4(8) . . ?
C18B C14B C15B 110.0(5) . . ?
C20 C14B C13B 16.5(5) . . ?
C18B C14B C13B 134.1(9) . . ?
C15B C14B C13B 115.7(8) . . ?
C16B C15B C14B 119.4(5) . . ?
C16B C15B H15B 120.3 . . ?
C14B C15B H15B 120.3 . . ?
N2B C16B C15B 132.3(6) . . ?
N2B C16B C17B 37.1(3) . . ?
C15B C16B C17B 95.2(4) . . ?
N2B C16B H16B 113.8 . . ?
C15B C16B H16B 113.8 . . ?
C17B C16B H16B 150.9 . . ?
C16B N2B C17B 106.7(6) . . ?
N2B C17B C18B 133.0(7) . . ?
N2B C17B C16B 36.2(4) . . ?
C18B C17B C16B 96.8(5) . . ?
N2B C17B H17B 113.5 . . ?
C18B C17B H17B 113.5 . . ?
C16B C17B H17B 149.7 . . ?
C17B C18B C14B 118.6(5) . . ?
C17B C18B H18B 120.7 . . ?
C14B C18B H18B 120.7 . . ?
C20 C19 C9 175(2) . . ?
C19 C20 C14B 175.7(18) . . ?

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 2.7491(12) 174.8 1_556 yes
O2 H2A N2A^a 0.82 1.97 2.79(2) 176.8 2_666 yes
O2 H2A N2B^b 0.82 1.88 2.699(8) 177.4 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_BA25_190
_database_code_depnum_ccdc_archive 'CCDC 1995712'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT906_A75_BA25_190        
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.545 Check 
RESPONSE: Due to diffuse scattering around Bragg peaks.
;
# end Validation Reply Form

_audit_creation_date             2019-11-07T15:14:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C16.53 H14 N3.47 O2'
_chemical_formula_weight         293.15

#----------------------------------------------------------------------------#
#                   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                   7.9981(2)
_cell_length_b                   9.7278(3)
_cell_length_c                   10.8484(3)
_cell_angle_alpha                93.160(2)
_cell_angle_beta                 106.919(3)
_cell_angle_gamma                113.993(3)
_cell_volume                     723.07(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    6964
_cell_measurement_theta_min      4.325
_cell_measurement_theta_max      75.615

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

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.026
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             307
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 4 3 0.1092
4 -4 -4 0.116
3 3 -4 0.045
3 -5 -4 0.107
1 -5 5 0.0227
-1 5 -5 0.001
-2 5 4 0.0741
-4 0 0 0.0879
4 0 0 0.0687
0 -4 -4 0.1248


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

_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
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  0.731
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.861
_shelx_estimated_absorpt_T_max   0.981

#----------------------------------------------------------------------------#
#                   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      -0.0086956
_diffrn_orient_matrix_ub_12      -0.0975026
_diffrn_orient_matrix_ub_13      0.1072505
_diffrn_orient_matrix_ub_21      -0.1966394
_diffrn_orient_matrix_ub_22      -0.1266289
_diffrn_orient_matrix_ub_23      -0.0930622
_diffrn_orient_matrix_ub_31      0.1079728
_diffrn_orient_matrix_ub_32      -0.0757554
_diffrn_orient_matrix_ub_33      -0.0526518
_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     0.0509
_diffrn_reflns_number            12658
_diffrn_reflns_limit_h_min       -8
_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       12
_diffrn_reflns_theta_min         4.346
_diffrn_reflns_theta_max         77.277
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.957
_reflns_Friedel_coverage         0
_reflns_number_total             2940
_reflns_number_gt                2582
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_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)+(0.0644P)²+0.1093P] 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         2940
_refine_ls_number_parameters     284
_refine_ls_number_restraints     507
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1204
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.041

#----------------------------------------------------------------------------#
#                   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 0.74 to 0.26 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 0.16517(13) 0.15800(11) 0.31162(9) 0.0438(3) Uani 1 1 d . . . . .
H1 H 0.198076 0.183652 0.393443 0.066 Uiso 1 1 calc R U . . .
O2 O 0.82273(14) 0.21855(13) 0.43560(10) 0.0513(3) Uani 1 1 d . . . . .
H2A H 0.826203 0.254066 0.509147 0.077 Uiso 1 1 calc R U . . .
N1 N 0.26182(16) 0.24884(14) -0.42111(11) 0.0448(3) Uani 1 1 d . . . . .
C1 C 0.31701(18) 0.15430(13) 0.28157(12) 0.0362(3) Uani 1 1 d . . . . .
C2 C 0.49301(18) 0.18614(13) 0.37827(12) 0.0371(3) Uani 1 1 d . . . . .
H2 H 0.508931 0.210141 0.468276 0.044 Uiso 1 1 calc R U . . .
C3 C 0.64622(19) 0.18303(14) 0.34379(12) 0.0389(3) Uani 1 1 d . . . . .
C4 C 0.6219(2) 0.14352(15) 0.21230(14) 0.0446(3) Uani 1 1 d . . . . .
H4 H 0.724576 0.138365 0.188172 0.054 Uiso 1 1 calc R U . . .
C5 C 0.4452(2) 0.11188(16) 0.11735(13) 0.0465(3) Uani 1 1 d . . . . .
H5 H 0.428427 0.085894 0.027433 0.056 Uiso 1 1 calc R U . . .
C6 C 0.2920(2) 0.11698(15) 0.14957(13) 0.0428(3) Uani 1 1 d . . . . .
H6 H 0.17222 0.095406 0.082823 0.051 Uiso 1 1 calc R U . . .
C7 C 0.3267(2) 0.39824(16) -0.37179(15) 0.0492(3) Uani 1 1 d . . . . .
H7 H 0.377712 0.471004 -0.422086 0.059 Uiso 1 1 calc R U . . .
C8 C 0.3237(2) 0.45224(16) -0.25274(15) 0.0473(3) Uani 1 1 d . . . . .
H8 H 0.372931 0.559094 -0.221096 0.057 Uiso 1 1 calc R U . . .
C9 C 0.24662(19) 0.34575(15) -0.18092(13) 0.0400(3) Uani 1 1 d D . . . .
C10 C 0.18204(19) 0.19104(15) -0.22869(13) 0.0409(3) Uani 1 1 d . . . . .
H10 H 0.131148 0.116086 -0.180003 0.049 Uiso 1 1 calc R U . . .
C11 C 0.19323(19) 0.14837(15) -0.34822(13) 0.0419(3) Uani 1 1 d . . . . .
H11 H 0.150115 0.042489 -0.380246 0.05 Uiso 1 1 calc R U . . .
N2A N 0.2113(7) 0.3767(4) -0.0566(4) 0.0351(9) Uani 0.696(13) 1 d D U P A 1
N3A N 0.2669(4) 0.5152(4) -0.0170(4) 0.0361(8) Uani 0.696(13) 1 d D U P A 1
C12A C 0.2319(8) 0.5539(6) 0.0995(5) 0.0320(8) Uani 0.696(13) 1 d . U P A 1
C13A C 0.2866(10) 0.7073(5) 0.1452(5) 0.0379(9) Uani 0.696(13) 1 d . U P A 1
H13A H 0.344817 0.784098 0.100185 0.045 Uiso 0.696(13) 1 calc R U P A 1
C14A C 0.2541(12) 0.7454(5) 0.2582(7) 0.0419(14) Uani 0.696(13) 1 d . U P A 1
H14A H 0.292681 0.850776 0.289189 0.05 Uiso 0.696(13) 1 calc R U P A 1
N4A N 0.1734(11) 0.6459(7) 0.3255(6) 0.0394(9) Uani 0.696(13) 1 d . U P A 1
C15A C 0.1201(9) 0.4998(6) 0.2797(5) 0.0385(8) Uani 0.696(13) 1 d . U P A 1
H15A H 0.060144 0.426045 0.326328 0.046 Uiso 0.696(13) 1 calc R U P A 1
C16A C 0.1456(7) 0.4471(4) 0.1688(5) 0.0355(8) Uani 0.696(13) 1 d . U P A 1
H16A H 0.105213 0.340768 0.140864 0.043 Uiso 0.696(13) 1 calc R U P A 1
C12B C 0.2136(18) 0.5247(12) 0.1243(10) 0.034(2) Uani 0.304(13) 1 d DG U P A 2
C13B C 0.283(2) 0.6833(12) 0.1493(13) 0.046(3) Uani 0.304(13) 1 d G U P A 2
H13B H 0.343548 0.742374 0.09416 0.055 Uiso 0.304(13) 1 calc R U P A 2
C14B C 0.263(3) 0.7555(11) 0.2548(16) 0.045(3) Uani 0.304(13) 1 d G U P A 2
H14B H 0.310831 0.863911 0.271839 0.054 Uiso 0.304(13) 1 calc R U P A 2
N4B N 0.175(3) 0.6691(16) 0.3354(13) 0.047(2) Uani 0.304(13) 1 d G U P A 2
C15B C 0.1054(19) 0.5105(15) 0.3105(12) 0.044(2) Uani 0.304(13) 1 d G U P A 2
H15B H 0.044793 0.451444 0.365568 0.053 Uiso 0.304(13) 1 calc R U P A 2
C16B C 0.1249(16) 0.4383(10) 0.2049(12) 0.043(2) Uani 0.304(13) 1 d G U P A 2
H16B H 0.077508 0.329904 0.187889 0.052 Uiso 0.304(13) 1 calc R U P A 2
C17 C 0.2339(15) 0.4632(18) 0.0184(9) 0.043(2) Uani 0.263(14) 1 d D U P A 2
C18 C 0.253(2) 0.412(2) -0.0753(12) 0.042(2) Uani 0.263(14) 1 d D U P A 2
N2B N 0.292(7) 0.485(8) -0.055(6) 0.044(6) Uani 0.037(6) 1 d D U P A 3
N3B N 0.177(8) 0.378(7) -0.019(6) 0.052(8) Uani 0.037(6) 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 1.3591(16) . ?
O1 H1 0.84 . ?
O2 C3 1.3607(16) . ?
O2 H2A 0.84 . ?
N1 C11 1.3354(18) . ?
N1 C7 1.3442(18) . ?
C1 C2 1.3885(18) . ?
C1 C6 1.3926(18) . ?
C2 C3 1.3921(18) . ?
C2 H2 0.95 . ?
C3 C4 1.3920(18) . ?
C4 C5 1.385(2) . ?
C4 H4 0.95 . ?
C5 C6 1.387(2) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.378(2) . ?
C7 H7 0.95 . ?
C8 C9 1.382(2) . ?
C8 H8 0.95 . ?
C9 C18 1.262(11) . ?
C9 C10 1.3879(18) . ?
C9 N2A 1.495(5) . ?
C9 N2B 1.72(8) . ?
C10 C11 1.3785(18) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
N2A N3A 1.238(5) . ?
N3A C12A 1.435(6) . ?
C12A C16A 1.387(4) . ?
C12A C13A 1.387(4) . ?
C13A C14A 1.387(4) . ?
C13A H13A 0.95 . ?
C14A N4A 1.316(4) . ?
C14A H14A 0.95 . ?
N4A C15A 1.324(4) . ?
C15A C16A 1.382(4) . ?
C15A H15A 0.95 . ?
C16A H16A 0.95 . ?
C12B C17 1.348(10) . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
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 1.182(15) . ?
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 117.18(12) . . ?
O1 C1 C2 121.80(11) . . ?
O1 C1 C6 118.10(12) . . ?
C2 C1 C6 120.10(12) . . ?
C1 C2 C3 120.24(11) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
O2 C3 C4 118.01(12) . . ?
O2 C3 C2 121.85(11) . . ?
C4 C3 C2 120.14(12) . . ?
C5 C4 C3 118.72(13) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.97(12) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.79(13) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C8 123.98(13) . . ?
N1 C7 H7 118 . . ?
C8 C7 H7 118 . . ?
C7 C8 C9 117.76(13) . . ?
C7 C8 H8 121.1 . . ?
C9 C8 H8 121.1 . . ?
C18 C9 C8 110.5(9) . . ?
C18 C9 C10 130.2(9) . . ?
C8 C9 C10 119.29(13) . . ?
C8 C9 N2A 126.85(18) . . ?
C10 C9 N2A 113.74(18) . . ?
C8 C9 N2B 92.8(14) . . ?
C10 C9 N2B 147.8(14) . . ?
C11 C10 C9 118.64(13) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
N1 C11 C10 123.10(12) . . ?
N1 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
N3A N2A C9 112.7(5) . . ?
N2A N3A C12A 116.0(5) . . ?
C16A C12A C13A 118.1(3) . . ?
C16A C12A N3A 124.0(3) . . ?
C13A C12A N3A 117.9(4) . . ?
C14A C13A C12A 118.2(3) . . ?
C14A C13A H13A 120.9 . . ?
C12A C13A H13A 120.9 . . ?
N4A C14A C13A 124.5(3) . . ?
N4A C14A H14A 117.7 . . ?
C13A C14A H14A 117.7 . . ?
C14A N4A C15A 116.5(3) . . ?
N4A C15A C16A 124.6(3) . . ?
N4A C15A H15A 117.7 . . ?
C16A C15A H15A 117.7 . . ?
C15A C16A C12A 118.1(2) . . ?
C15A C16A H16A 121 . . ?
C12A C16A H16A 121 . . ?
C17 C12B C13B 116.4(8) . . ?
C17 C12B C16B 123.6(8) . . ?
C13B C12B C16B 120 . . ?
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 . . ?
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 179(2) . . ?
C17 C18 C9 171.8(18) . . ?
N3B N2B C9 85(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 0.84 1.93 2.7645(15) 176.1 1_556 yes
O2 H2A N4A 0.84 1.99 2.829(4) 174 2_666 yes
O2 H2A N4B 0.84 1.81 2.65(6) 177.9 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_BA25_210
_database_code_depnum_ccdc_archive 'CCDC 1995713'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT906_A75_BA25_210        
;
PROBLEM: Large K Value in the Analysis of Variance ......      3.550 Check 
RESPONSE: Due to diffuse scattering around Bragg peaks.
;
# end Validation Reply Form

_audit_creation_date             2019-11-07T15:20:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C16.51 H14 N3.49 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                   8.01758(17)
_cell_length_b                   9.7320(2)
_cell_length_c                   10.86038(18)
_cell_angle_alpha                93.3010(15)
_cell_angle_beta                 106.8700(17)
_cell_angle_gamma                113.897(2)
_cell_volume                     726.41(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    6475
_cell_measurement_theta_min      4.322
_cell_measurement_theta_max      77.279

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

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.026
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             307
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 4 3 0.1092
4 0 0 0.0687
0 5 -5 0.001
-2 5 4 0.0741
3 -5 -4 0.107
-4 0 0 0.0879
3 3 -3 0.045
1 -5 5 0.0227
4 -4 -4 0.116
0 -4 -4 0.1248


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

_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
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  0.724
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.862
_shelx_estimated_absorpt_T_max   0.981

#----------------------------------------------------------------------------#
#                   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      -0.0203814
_diffrn_orient_matrix_ub_12      -0.103266
_diffrn_orient_matrix_ub_13      0.1023517
_diffrn_orient_matrix_ub_21      -0.1950044
_diffrn_orient_matrix_ub_22      -0.1211712
_diffrn_orient_matrix_ub_23      -0.0988111
_diffrn_orient_matrix_ub_31      0.1078696
_diffrn_orient_matrix_ub_32      -0.0766998
_diffrn_orient_matrix_ub_33      -0.0514786
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_number            12586
_diffrn_reflns_limit_h_min       -8
_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       12
_diffrn_reflns_theta_min         4.342
_diffrn_reflns_theta_max         77.421
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.952
_reflns_Friedel_coverage         0
_reflns_number_total             2942
_reflns_number_gt                2484
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_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)+(0.0718P)²+0.0823P] 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(11)
_refine_ls_number_reflns         2942
_refine_ls_number_parameters     284
_refine_ls_number_restraints     507
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1318
_refine_ls_wR_factor_gt          0.1256
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   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 0.75 to 0.25 with the amount 
 of 4,4'-azopyridine in the secondary position calculated at 0.06. The 
 inconsistent reflections -6 8 9, -6 9 7, and -7 7 4 were omitted. 
;

#----------------------------------------------------------------------------#
#                   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 0.16575(14) 0.15725(12) 0.31168(10) 0.0494(3) Uani 1 1 d . . . . .
H1 H 0.19643 0.178637 0.392646 0.074 Uiso 1 1 calc R U . . .
O2 O 0.82176(15) 0.21831(14) 0.43541(11) 0.0575(3) Uani 1 1 d . . . . .
H2A H 0.825105 0.253147 0.508128 0.086 Uiso 1 1 calc R U . . .
N1 N 0.26145(18) 0.24845(15) -0.42117(12) 0.0495(3) Uani 1 1 d . . . . .
C1 C 0.31733(19) 0.15377(14) 0.28155(13) 0.0406(3) Uani 1 1 d . . . . .
C2 C 0.4929(2) 0.18567(14) 0.37812(13) 0.0410(3) Uani 1 1 d . . . . .
H2 H 0.508358 0.209305 0.467092 0.049 Uiso 1 1 calc R U . . .
C3 C 0.6458(2) 0.18282(15) 0.34391(13) 0.0438(3) Uani 1 1 d . . . . .
C4 C 0.6216(2) 0.14366(17) 0.21254(15) 0.0498(4) Uani 1 1 d . . . . .
H4 H 0.723035 0.138863 0.188533 0.06 Uiso 1 1 calc R U . . .
C5 C 0.4453(2) 0.11186(17) 0.11781(14) 0.0520(4) Uani 1 1 d . . . . .
H5 H 0.42877 0.086226 0.028892 0.062 Uiso 1 1 calc R U . . .
C6 C 0.2926(2) 0.11666(16) 0.14997(14) 0.0478(3) Uani 1 1 d . . . . .
H6 H 0.174399 0.095206 0.084006 0.057 Uiso 1 1 calc R U . . .
C7 C 0.3267(2) 0.39795(18) -0.37211(17) 0.0539(4) Uani 1 1 d . . . . .
H7 H 0.377435 0.469595 -0.421798 0.065 Uiso 1 1 calc R U . . .
C8 C 0.3236(2) 0.45213(17) -0.25343(16) 0.0527(4) Uani 1 1 d . . . . .
H8 H 0.372213 0.557868 -0.22235 0.063 Uiso 1 1 calc R U . . .
C9 C 0.2469(2) 0.34637(16) -0.18109(14) 0.0448(3) Uani 1 1 d D . . . .
C10 C 0.1823(2) 0.19188(16) -0.22900(14) 0.0460(3) Uani 1 1 d . . . . .
H10 H 0.131983 0.117977 -0.180883 0.055 Uiso 1 1 calc R U . . .
C11 C 0.1931(2) 0.14871(16) -0.34804(14) 0.0471(3) Uani 1 1 d . . . . .
H11 H 0.150372 0.043894 -0.379547 0.056 Uiso 1 1 calc R U . . .
N2A N 0.2115(7) 0.3765(4) -0.0572(4) 0.0391(9) Uani 0.690(12) 1 d D U P A 1
N3A N 0.2664(4) 0.5148(4) -0.0166(4) 0.0409(9) Uani 0.690(12) 1 d D U P A 1
C12A C 0.2315(9) 0.5543(6) 0.1002(5) 0.0367(9) Uani 0.690(12) 1 d . U P A 1
C13A C 0.2860(11) 0.7070(6) 0.1458(6) 0.0438(10) Uani 0.690(12) 1 d . U P A 1
H13A H 0.343514 0.782986 0.101587 0.053 Uiso 0.690(12) 1 calc R U P A 1
C14A C 0.2534(13) 0.7450(6) 0.2589(7) 0.0471(14) Uani 0.690(12) 1 d . U P A 1
H14A H 0.291271 0.849113 0.289701 0.057 Uiso 0.690(12) 1 calc R U P A 1
N4A N 0.1734(13) 0.6456(8) 0.3258(7) 0.0447(10) Uani 0.690(12) 1 d . U P A 1
C15A C 0.1202(10) 0.4992(7) 0.2794(6) 0.0446(9) Uani 0.690(12) 1 d . U P A 1
H15A H 0.060843 0.426162 0.325227 0.054 Uiso 0.690(12) 1 calc R U P A 1
C16A C 0.1459(8) 0.4472(5) 0.1692(5) 0.0408(9) Uani 0.690(12) 1 d . U P A 1
H16A H 0.106656 0.34214 0.141386 0.049 Uiso 0.690(12) 1 calc R U P A 1
C12B C 0.213(2) 0.5226(13) 0.1224(11) 0.039(2) Uani 0.310(12) 1 d DG U P A 2
C13B C 0.283(2) 0.6812(13) 0.1473(14) 0.047(2) Uani 0.310(12) 1 d G U P A 2
H13B H 0.342127 0.739139 0.092669 0.057 Uiso 0.310(12) 1 calc R U P A 2
C14B C 0.264(3) 0.7540(12) 0.2531(17) 0.050(3) Uani 0.310(12) 1 d G U P A 2
H14B H 0.311338 0.861197 0.269949 0.06 Uiso 0.310(12) 1 calc R U P A 2
N4B N 0.176(3) 0.6682(17) 0.3340(15) 0.050(3) Uani 0.310(12) 1 d G U P A 2
C15B C 0.107(2) 0.5097(16) 0.3091(13) 0.048(2) Uani 0.310(12) 1 d G U P A 2
H15B H 0.047113 0.451713 0.363744 0.058 Uiso 0.310(12) 1 calc R U P A 2
C16B C 0.1250(19) 0.4369(11) 0.2033(12) 0.049(2) Uani 0.310(12) 1 d G U P A 2
H16B H 0.0779 0.329653 0.186465 0.059 Uiso 0.310(12) 1 calc R U P A 2
C17 C 0.2340(17) 0.462(2) 0.0194(10) 0.046(2) Uani 0.254(15) 1 d D U P A 2
C18 C 0.254(2) 0.415(2) -0.0753(13) 0.047(3) Uani 0.254(15) 1 d D U P A 2
N2B N 0.296(5) 0.485(6) -0.057(4) 0.047(5) Uani 0.056(6) 1 d D U P A 3
N3B N 0.180(5) 0.395(5) -0.011(5) 0.048(6) Uani 0.056(6) 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 1.3594(17) . ?
O1 H1 0.83 . ?
O2 C3 1.3596(17) . ?
O2 H2A 0.83 . ?
N1 C11 1.335(2) . ?
N1 C7 1.344(2) . ?
C1 C2 1.3889(19) . ?
C1 C6 1.3893(19) . ?
C2 C3 1.391(2) . ?
C2 H2 0.94 . ?
C3 C4 1.391(2) . ?
C4 C5 1.385(2) . ?
C4 H4 0.94 . ?
C5 C6 1.384(2) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.375(2) . ?
C7 H7 0.94 . ?
C8 C9 1.384(2) . ?
C8 H8 0.94 . ?
C9 C18 1.270(12) . ?
C9 C10 1.3864(19) . ?
C9 N2A 1.490(5) . ?
C9 N2B 1.68(6) . ?
C10 C11 1.374(2) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
N2A N3A 1.240(5) . ?
N3A C12A 1.439(6) . ?
C12A C13A 1.382(4) . ?
C12A C16A 1.389(4) . ?
C13A C14A 1.387(4) . ?
C13A H13A 0.94 . ?
C14A N4A 1.313(4) . ?
C14A H14A 0.94 . ?
N4A C15A 1.329(4) . ?
C15A C16A 1.375(5) . ?
C15A H15A 0.94 . ?
C16A H16A 0.94 . ?
C12B C17 1.320(11) . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
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 1.180(15) . ?
N2B N3B 1.24(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 117.18(13) . . ?
O1 C1 C2 121.79(12) . . ?
O1 C1 C6 118.11(12) . . ?
C2 C1 C6 120.10(13) . . ?
C1 C2 C3 120.36(12) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.03(12) . . ?
O2 C3 C4 118.00(13) . . ?
C2 C3 C4 119.97(13) . . ?
C5 C4 C3 118.73(14) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C6 C5 C4 122.05(13) . . ?
C6 C5 H5 119 . . ?
C4 C5 H5 119 . . ?
C5 C6 C1 118.77(14) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C8 123.78(14) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.04(14) . . ?
C7 C8 H8 121 . . ?
C9 C8 H8 121 . . ?
C18 C9 C8 110.1(9) . . ?
C18 C9 C10 130.9(9) . . ?
C8 C9 C10 118.96(14) . . ?
C8 C9 N2A 127.5(2) . . ?
C10 C9 N2A 113.42(19) . . ?
C8 C9 N2B 92.5(10) . . ?
C10 C9 N2B 148.4(10) . . ?
C11 C10 C9 118.82(14) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.18(13) . . ?
N1 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
N3A N2A C9 112.9(5) . . ?
N2A N3A C12A 116.7(5) . . ?
C13A C12A C16A 118.3(3) . . ?
C13A C12A N3A 118.1(4) . . ?
C16A C12A N3A 123.5(3) . . ?
C12A C13A C14A 118.1(3) . . ?
C12A C13A H13A 121 . . ?
C14A C13A H13A 121 . . ?
N4A C14A C13A 124.5(3) . . ?
N4A C14A H14A 117.7 . . ?
C13A C14A H14A 117.7 . . ?
C14A N4A C15A 116.4(3) . . ?
N4A C15A C16A 124.6(3) . . ?
N4A C15A H15A 117.7 . . ?
C16A C15A H15A 117.7 . . ?
C15A C16A C12A 118.0(3) . . ?
C15A C16A H16A 121 . . ?
C12A C16A H16A 121 . . ?
C17 C12B C13B 116.3(9) . . ?
C17 C12B C16B 123.7(9) . . ?
C13B C12B C16B 120 . . ?
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 . . ?
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 176(2) . . ?
C17 C18 C9 171(2) . . ?
N3B N2B C9 93(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 1.94 2.7666(16) 173.4 1_556 yes
O2 H2A N4A 0.83 2 2.826(5) 173.8 2_666 yes
O2 H2A N4B 0.83 1.84 2.67(7) 177.6 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_A50_BA50_230
_database_code_depnum_ccdc_archive 'CCDC 1995708'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT041_A50_BA50_230        
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check 
RESPONSE: Due to the partial occupancy of the 4,4'-azopyridine and 
          bis(4-pyridyl)acetylene molecules.
;
_vrf_PLAT077_A50_BA50_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_PLAT906_A50_BA50_230        
;
PROBLEM: Large K Value in the Analysis of Variance ......      7.054 Check 
RESPONSE: Due to diffuse scattering about the Bragg peaks.
;
# end Validation Reply Form

_audit_creation_date             2019-11-11T13:39:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C16.94 H14 N3.06 O2'
_chemical_formula_weight         292.33

#----------------------------------------------------------------------------#
#                   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                   8.08726(15)
_cell_length_b                   9.7628(2)
_cell_length_c                   10.91257(18)
_cell_angle_alpha                93.0131(15)
_cell_angle_beta                 107.2723(16)
_cell_angle_gamma                114.0439(19)
_cell_volume                     736.33(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    7339
_cell_measurement_theta_min      4.282
_cell_measurement_theta_max      76.217

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

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.052
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             306
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 1 -7 0.0847
2 -1 5 0.0871
-2 -1 7 0.1232
1 -3 6 0.0981
0 -5 -1 0.0393
5 -3 -3 0.116
0 5 1 0.0131
-5 2 2 0.1027
-3 2 7 0.1163
5 -2 0 0.1098
0 -5 4 0.0805
4 2 -1 0.0622
5 -5 0 0.1116
-5 2 3 0.1092
-5 3 -2 0.1167


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

_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
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  0.458
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.848
_shelx_estimated_absorpt_T_max   0.963

#----------------------------------------------------------------------------#
#                   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      0.0433832
_diffrn_orient_matrix_ub_12      -0.0528815
_diffrn_orient_matrix_ub_13      0.1314308
_diffrn_orient_matrix_ub_21      -0.1207368
_diffrn_orient_matrix_ub_22      -0.1681683
_diffrn_orient_matrix_ub_23      -0.0725101
_diffrn_orient_matrix_ub_31      0.1819003
_diffrn_orient_matrix_ub_32      -0.0032909
_diffrn_orient_matrix_ub_33      -0.0150376
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_number            15670
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_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         4.329
_diffrn_reflns_theta_max         77.358
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_reflns_Friedel_coverage         0
_reflns_number_total             3013
_reflns_number_gt                2579
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_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)+(0.0547P)²+0.1269P] 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       0.0031(8)
_refine_ls_number_reflns         3013
_refine_ls_number_parameters     284
_refine_ls_number_restraints     513
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.124
_refine_ls_wR_factor_gt          0.1199
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.144
_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)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 0.53 to 0.47 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 0.16679(14) 0.15185(12) 0.30958(10) 0.0550(3) Uani 1 1 d . . . . .
H1 H 0.199166 0.176381 0.390145 0.082 Uiso 1 1 calc R U . . .
O2 O 0.81884(16) 0.21461(15) 0.43442(11) 0.0642(3) Uani 1 1 d . . . . .
H2A H 0.823298 0.250256 0.506719 0.096 Uiso 1 1 calc R U . . .
N1 N 0.26169(18) 0.24580(15) -0.42542(12) 0.0555(3) Uani 1 1 d . . . . .
C1 C 0.3178(2) 0.15022(14) 0.27977(13) 0.0450(3) Uani 1 1 d . . . . .
C2 C 0.4924(2) 0.18173(15) 0.37667(13) 0.0450(3) Uani 1 1 d . . . . .
H2 H 0.507704 0.204161 0.465315 0.054 Uiso 1 1 calc R U . . .
C3 C 0.6441(2) 0.18020(16) 0.34300(14) 0.0490(3) Uani 1 1 d . . . . .
C4 C 0.6199(2) 0.14309(17) 0.21199(16) 0.0567(4) Uani 1 1 d . . . . .
H4 H 0.720905 0.139325 0.188353 0.068 Uiso 1 1 calc R U . . .
C5 C 0.4454(3) 0.11191(18) 0.11727(15) 0.0595(4) Uani 1 1 d . . . . .
H5 H 0.429163 0.087452 0.028678 0.071 Uiso 1 1 calc R U . . .
C6 C 0.2938(2) 0.11561(17) 0.14896(14) 0.0543(4) Uani 1 1 d . . . . .
H6 H 0.176499 0.095003 0.082912 0.065 Uiso 1 1 calc R U . . .
C7 C 0.3280(2) 0.39511(19) -0.37951(18) 0.0622(4) Uani 1 1 d . . . . .
H7 H 0.376965 0.46463 -0.430817 0.075 Uiso 1 1 calc R U . . .
C8 C 0.3286(2) 0.45251(18) -0.26186(17) 0.0600(4) Uani 1 1 d . . . . .
H8 H 0.378939 0.558519 -0.232599 0.072 Uiso 1 1 calc R U . . .
C9 C 0.2529(2) 0.34985(17) -0.18721(14) 0.0489(3) Uani 1 1 d D . . . .
C10 C 0.1867(2) 0.19513(16) -0.23251(14) 0.0507(3) Uani 1 1 d . . . . .
H10 H 0.137266 0.123052 -0.183158 0.061 Uiso 1 1 calc R U . . .
C11 C 0.1947(2) 0.14892(17) -0.35063(15) 0.0526(4) Uani 1 1 d . . . . .
H11 H 0.150799 0.043833 -0.380357 0.063 Uiso 1 1 calc R U . . .
N2A N 0.2143(12) 0.3790(8) -0.0596(7) 0.0445(14) Uani 0.478(13) 1 d D U P A 1
N3A N 0.2652(7) 0.5131(7) -0.0165(7) 0.0479(13) Uani 0.478(13) 1 d D U P A 1
C12A C 0.2314(14) 0.5532(9) 0.1002(8) 0.0406(12) Uani 0.478(13) 1 d . U P A 1
C13A C 0.2816(17) 0.7050(10) 0.1471(9) 0.0502(16) Uani 0.478(13) 1 d . U P A 1
H13A H 0.33579 0.782698 0.103567 0.06 Uiso 0.478(13) 1 calc R U P A 1
C14A C 0.249(2) 0.7378(10) 0.2601(12) 0.052(2) Uani 0.478(13) 1 d . U P A 1
H14A H 0.286118 0.841291 0.291609 0.062 Uiso 0.478(13) 1 calc R U P A 1
N4A N 0.1737(19) 0.6420(11) 0.3259(9) 0.0494(14) Uani 0.478(13) 1 d . U P A 1
C15A C 0.1253(14) 0.5006(10) 0.2784(9) 0.0481(15) Uani 0.478(13) 1 d . U P A 1
H15A H 0.069165 0.426842 0.324432 0.058 Uiso 0.478(13) 1 calc R U P A 1
C16A C 0.1475(12) 0.4478(8) 0.1688(8) 0.0466(14) Uani 0.478(13) 1 d . U P A 1
H16A H 0.106785 0.342835 0.14115 0.056 Uiso 0.478(13) 1 calc R U P A 1
C12B C 0.2120(12) 0.5254(9) 0.1250(7) 0.0417(14) Uani 0.522(13) 1 d DG U P A 2
C13B C 0.2818(15) 0.6836(8) 0.1510(9) 0.0521(18) Uani 0.522(13) 1 d G U P A 2
H13B H 0.34203 0.742448 0.097535 0.063 Uiso 0.522(13) 1 calc R U P A 2
C14B C 0.2624(19) 0.7548(7) 0.2560(10) 0.052(2) Uani 0.522(13) 1 d G U P A 2
H14B H 0.309559 0.861719 0.273575 0.063 Uiso 0.522(13) 1 calc R U P A 2
N4B N 0.1733(18) 0.6678(9) 0.3350(9) 0.0522(15) Uani 0.522(13) 1 d G U P A 2
C15B C 0.1036(12) 0.5096(9) 0.3091(7) 0.0473(13) Uani 0.522(13) 1 d G U P A 2
H15B H 0.043289 0.450754 0.36251 0.057 Uiso 0.522(13) 1 calc R U P A 2
C16B C 0.1229(11) 0.4384(6) 0.2040(7) 0.0473(14) Uani 0.522(13) 1 d G U P A 2
H16B H 0.075759 0.33148 0.18647 0.057 Uiso 0.522(13) 1 calc R U P A 2
C17 C 0.2325(10) 0.4609(12) 0.0178(6) 0.0456(17) Uani 0.468(19) 1 d D U P A 2
C18 C 0.2543(14) 0.4153(13) -0.0777(9) 0.0487(19) Uani 0.468(19) 1 d D U P A 2
N2B N 0.284(7) 0.473(6) -0.067(5) 0.052(5) Uani 0.049(8) 1 d D U P A 3
N3B N 0.181(7) 0.395(7) -0.008(5) 0.058(8) Uani 0.049(8) 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 1.3594(17) . ?
O1 H1 0.83 . ?
O2 C3 1.3584(18) . ?
O2 H2A 0.83 . ?
N1 C11 1.334(2) . ?
N1 C7 1.338(2) . ?
C1 C6 1.386(2) . ?
C1 C2 1.3901(19) . ?
C2 C3 1.387(2) . ?
C2 H2 0.94 . ?
C3 C4 1.391(2) . ?
C4 C5 1.379(2) . ?
C4 H4 0.94 . ?
C5 C6 1.382(2) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.371(2) . ?
C7 H7 0.94 . ?
C8 C9 1.388(2) . ?
C8 H8 0.94 . ?
C9 C18 1.320(9) . ?
C9 C10 1.385(2) . ?
C9 N2A 1.551(8) . ?
C9 N2B 1.62(7) . ?
C10 C11 1.371(2) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
N2A N3A 1.219(9) . ?
N3A C12A 1.446(8) . ?
C12A C16A 1.376(6) . ?
C12A C13A 1.389(6) . ?
C13A C14A 1.383(6) . ?
C13A H13A 0.94 . ?
C14A N4A 1.276(7) . ?
C14A H14A 0.94 . ?
N4A C15A 1.300(7) . ?
C15A C16A 1.366(6) . ?
C15A H15A 0.94 . ?
C16A H16A 0.94 . ?
C12B C17 1.384(7) . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
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 1.199(11) . ?
N2B N3B 1.24(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 117.30(14) . . ?
O1 C1 C6 118.26(13) . . ?
O1 C1 C2 121.63(12) . . ?
C6 C1 C2 120.11(13) . . ?
C3 C2 C1 120.23(13) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
O2 C3 C2 122.09(13) . . ?
O2 C3 C4 118.01(13) . . ?
C2 C3 C4 119.90(14) . . ?
C5 C4 C3 119.00(14) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.86(14) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 118.89(14) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C8 123.74(15) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.19(14) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C18 C9 C10 127.5(5) . . ?
C18 C9 C8 113.8(5) . . ?
C10 C9 C8 118.66(14) . . ?
C10 C9 N2A 111.5(3) . . ?
C8 C9 N2A 129.6(3) . . ?
C10 C9 N2B 143.6(13) . . ?
C8 C9 N2B 97.7(13) . . ?
C11 C10 C9 118.84(14) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.22(14) . . ?
N1 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
N3A N2A C9 114.6(10) . . ?
N2A N3A C12A 119.3(10) . . ?
C16A C12A C13A 116.6(4) . . ?
C16A C12A N3A 123.6(5) . . ?
C13A C12A N3A 119.8(6) . . ?
C14A C13A C12A 117.7(5) . . ?
C14A C13A H13A 121.2 . . ?
C12A C13A H13A 121.2 . . ?
N4A C14A C13A 126.6(5) . . ?
N4A C14A H14A 116.7 . . ?
C13A C14A H14A 116.7 . . ?
C14A N4A C15A 114.3(5) . . ?
N4A C15A C16A 126.9(5) . . ?
N4A C15A H15A 116.5 . . ?
C16A C15A H15A 116.5 . . ?
C15A C16A C12A 117.9(4) . . ?
C15A C16A H16A 121 . . ?
C12A C16A H16A 121 . . ?
C17 C12B C13B 117.4(5) . . ?
C17 C12B C16B 122.6(5) . . ?
C13B C12B C16B 120 . . ?
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 175.1(13) . . ?
C17 C18 C9 171.9(13) . . ?
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 -179.55(12) . . . . ?
C6 C1 C2 C3 0.6(2) . . . . ?
C1 C2 C3 O2 178.08(13) . . . . ?
C1 C2 C3 C4 -1.7(2) . . . . ?
O2 C3 C4 C5 -178.21(14) . . . . ?
C2 C3 C4 C5 1.6(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
O1 C1 C6 C5 -179.30(13) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
C11 N1 C7 C8 -0.7(2) . . . . ?
N1 C7 C8 C9 -1.2(2) . . . . ?
C7 C8 C9 C18 -178.0(5) . . . . ?
C7 C8 C9 C10 2.3(2) . . . . ?
C7 C8 C9 N2A -172.7(4) . . . . ?
C7 C8 C9 N2B -178.6(18) . . . . ?
C18 C9 C10 C11 179.0(6) . . . . ?
C8 C9 C10 C11 -1.4(2) . . . . ?
N2A C9 C10 C11 174.4(3) . . . . ?
N2B C9 C10 C11 -180(3) . . . . ?
C7 N1 C11 C10 1.7(2) . . . . ?
C9 C10 C11 N1 -0.6(2) . . . . ?
C10 C9 N2A N3A -178.3(5) . . . . ?
C8 C9 N2A N3A -3.1(8) . . . . ?
C9 N2A N3A C12A 178.3(6) . . . . ?
N2A N3A C12A C16A 1.5(10) . . . . ?
N2A N3A C12A C13A -177.3(7) . . . . ?
C16A C12A C13A C14A 2.0(6) . . . . ?
N3A C12A C13A C14A -179.1(8) . . . . ?
C12A C13A C14A N4A -1.3(6) . . . . ?
C13A C14A N4A C15A 0.2(6) . . . . ?
C14A N4A C15A C16A 0.1(6) . . . . ?
N4A C15A C16A C12A 0.7(7) . . . . ?
C13A C12A C16A C15A -1.8(6) . . . . ?
N3A C12A C16A C15A 179.3(8) . . . . ?
C17 C12B C13B C14B 178.9(8) . . . . ?
C16B C12B C13B C14B 0 . . . . ?
C12B C13B C14B N4B 0 . . . . ?
C13B C14B N4B C15B 0 . . . . ?
C14B N4B C15B C16B 0 . . . . ?
N4B C15B C16B C12B 0 . . . . ?
C17 C12B C16B C15B -178.9(8) . . . . ?
C13B C12B C16B C15B 0 . . . . ?
C10 C9 N2B N3B -17(6) . . . . ?
C8 C9 N2B N3B 165(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 0.83 1.93 2.7609(16) 174.5 1_556 yes
O2 H2A N4A^a 0.83 2.05 2.874(8) 172.9 2_666 yes
O2 H2A N4B^b 0.83 1.85 2.68(4) 177.9 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_BA25_250
_database_code_depnum_ccdc_archive 'CCDC 1995715'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT906_A75_BA25_250        
;
PROBLEM: Large K Value in the Analysis of Variance ......      3.822 Check 
RESPONSE: Due to diffuse scattering around Bragg peaks.
;
# end Validation Reply Form

_audit_creation_date             2019-11-07T15:23:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C16.48 H14 N3.52 O2'
_chemical_formula_weight         293.34

#----------------------------------------------------------------------------#
#                   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                   8.0515(2)
_cell_length_b                   9.7483(3)
_cell_length_c                   10.8766(3)
_cell_angle_alpha                93.548(2)
_cell_angle_beta                 106.805(2)
_cell_angle_gamma                113.770(3)
_cell_volume                     732.24(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    5689
_cell_measurement_theta_min      4.321
_cell_measurement_theta_max      74.26

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

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.026
_exptl_crystal_density_diffrn    1.33
_exptl_crystal_F_000             307
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 4 3 0.1092
4 -4 -4 0.116
-2 4 4 0.0741
0 5 -5 0.001
3 3 -3 0.045
4 -1 1 0.0687
0 -5 5 0.0227
-4 1 -1 0.0879
0 -4 -4 0.1248
3 -5 -4 0.107


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

_exptl_absorpt_coefficient_mu    0.74
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
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  0.74
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.863
_shelx_estimated_absorpt_T_max   0.981

#----------------------------------------------------------------------------#
#                   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      -0.0335656
_diffrn_orient_matrix_ub_12      -0.109487
_diffrn_orient_matrix_ub_13      0.0960896
_diffrn_orient_matrix_ub_21      -0.1932235
_diffrn_orient_matrix_ub_22      -0.1135621
_diffrn_orient_matrix_ub_23      -0.1046583
_diffrn_orient_matrix_ub_31      0.105402
_diffrn_orient_matrix_ub_32      -0.0789017
_diffrn_orient_matrix_ub_33      -0.0515011
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_number            12763
_diffrn_reflns_limit_h_min       -8
_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       11
_diffrn_reflns_theta_min         4.337
_diffrn_reflns_theta_max         77.35
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.99
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.99
_diffrn_reflns_point_group_measured_fraction_max 0.948
_reflns_Friedel_coverage         0
_reflns_number_total             2954
_reflns_number_gt                2388
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_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)+(0.0740P)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       0.0048(12)
_refine_ls_number_reflns         2954
_refine_ls_number_parameters     284
_refine_ls_number_restraints     507
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1416
_refine_ls_wR_factor_gt          0.132
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.17
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   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 0.76 to 0.24 with the amount 
 of 4,4'-azopyridine in the secondary position calculated at 0.10. The 
 inconsistent reflections -5 8 9, -7 8 7, -6 9 7, -6 8 8, -5 9 8, -8 7 7, 
 -6 7 9, and -6 8 7 were omitted. 
;

#----------------------------------------------------------------------------#
#                   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 0.16648(15) 0.15534(13) 0.31181(10) 0.0590(3) Uani 1 1 d . . . . .
H1 H 0.197066 0.176747 0.392708 0.089 Uiso 1 1 calc R U . . .
O2 O 0.81979(17) 0.21785(15) 0.43492(12) 0.0692(4) Uani 1 1 d . . . . .
H2A H 0.823115 0.252961 0.507558 0.104 Uiso 1 1 calc R U . . .
N1 N 0.26116(19) 0.24786(16) -0.42113(13) 0.0579(4) Uani 1 1 d . . . . .
C1 C 0.3178(2) 0.15218(15) 0.28145(14) 0.0480(3) Uani 1 1 d . . . . .
C2 C 0.4925(2) 0.18444(16) 0.37808(14) 0.0492(3) Uani 1 1 d . . . . .
H2 H 0.507744 0.207803 0.466986 0.059 Uiso 1 1 calc R U . . .
C3 C 0.6447(2) 0.18224(17) 0.34353(15) 0.0522(4) Uani 1 1 d . . . . .
C4 C 0.6205(3) 0.14309(18) 0.21265(16) 0.0590(4) Uani 1 1 d . . . . .
H4 H 0.72131 0.138137 0.188542 0.071 Uiso 1 1 calc R U . . .
C5 C 0.4454(3) 0.11148(18) 0.11825(15) 0.0610(4) Uani 1 1 d . . . . .
H5 H 0.429255 0.086399 0.029373 0.073 Uiso 1 1 calc R U . . .
C6 C 0.2935(3) 0.11561(17) 0.15042(15) 0.0567(4) Uani 1 1 d . . . . .
H6 H 0.175734 0.093986 0.084584 0.068 Uiso 1 1 calc R U . . .
C7 C 0.3265(2) 0.3969(2) -0.37277(18) 0.0635(4) Uani 1 1 d . . . . .
H7 H 0.376775 0.467722 -0.422723 0.076 Uiso 1 1 calc R U . . .
C8 C 0.3242(3) 0.45226(19) -0.25428(18) 0.0629(4) Uani 1 1 d . . . . .
H8 H 0.372937 0.557974 -0.223424 0.075 Uiso 1 1 calc R U . . .
C9 C 0.2480(2) 0.34775(18) -0.18188(15) 0.0537(4) Uani 1 1 d D . . . .
C10 C 0.1832(2) 0.19393(18) -0.22923(15) 0.0558(4) Uani 1 1 d . . . . .
H10 H 0.133155 0.120759 -0.180975 0.067 Uiso 1 1 calc R U . . .
C11 C 0.1933(2) 0.14999(18) -0.34761(15) 0.0567(4) Uani 1 1 d . . . . .
H11 H 0.149918 0.045101 -0.378848 0.068 Uiso 1 1 calc R U . . .
N2A N 0.2116(8) 0.3769(5) -0.0579(4) 0.0475(10) Uani 0.665(12) 1 d D U P A 1
N3A N 0.2663(5) 0.5140(5) -0.0162(4) 0.0500(10) Uani 0.665(12) 1 d D U P A 1
C12A C 0.2322(10) 0.5541(6) 0.1008(5) 0.0426(9) Uani 0.665(12) 1 d . U P A 1
C13A C 0.2846(12) 0.7061(6) 0.1459(6) 0.0525(10) Uani 0.665(12) 1 d . U P A 1
H13A H 0.341476 0.782021 0.101894 0.063 Uiso 0.665(12) 1 calc R U P A 1
C14A C 0.2505(14) 0.7432(6) 0.2584(8) 0.0577(15) Uani 0.665(12) 1 d . U P A 1
H14A H 0.287159 0.846992 0.289103 0.069 Uiso 0.665(12) 1 calc R U P A 1
N4A N 0.1716(13) 0.6454(8) 0.3248(7) 0.0532(12) Uani 0.665(12) 1 d . U P A 1
C15A C 0.1206(11) 0.4999(8) 0.2789(6) 0.0523(10) Uani 0.665(12) 1 d . U P A 1
H15A H 0.06213 0.42713 0.324742 0.063 Uiso 0.665(12) 1 calc R U P A 1
C16A C 0.1470(8) 0.4476(5) 0.1687(6) 0.0482(11) Uani 0.665(12) 1 d . U P A 1
H16A H 0.108169 0.342798 0.14066 0.058 Uiso 0.665(12) 1 calc R U P A 1
C12B C 0.2090(18) 0.5169(12) 0.1206(10) 0.046(2) Uani 0.335(12) 1 d DG U P A 2
C13B C 0.283(2) 0.6755(12) 0.1464(12) 0.057(2) Uani 0.335(12) 1 d G U P A 2
H13B H 0.341473 0.732361 0.09133 0.068 Uiso 0.335(12) 1 calc R U P A 2
C14B C 0.269(3) 0.7502(11) 0.2537(15) 0.058(3) Uani 0.335(12) 1 d G U P A 2
H14B H 0.319113 0.857416 0.271141 0.069 Uiso 0.335(12) 1 calc R U P A 2
N4B N 0.182(3) 0.6661(16) 0.3351(13) 0.060(3) Uani 0.335(12) 1 d G U P A 2
C15B C 0.109(2) 0.5075(15) 0.3093(11) 0.055(2) Uani 0.335(12) 1 d G U P A 2
H15B H 0.049834 0.450721 0.364374 0.066 Uiso 0.335(12) 1 calc R U P A 2
C16B C 0.1220(17) 0.4329(10) 0.2020(11) 0.053(2) Uani 0.335(12) 1 d G U P A 2
H16B H 0.072192 0.325663 0.184564 0.064 Uiso 0.335(12) 1 calc R U P A 2
C17 C 0.231(2) 0.460(3) 0.0190(11) 0.052(3) Uani 0.239(16) 1 d D U P A 2
C18 C 0.257(2) 0.417(3) -0.0746(14) 0.054(3) Uani 0.239(16) 1 d D U P A 2
N2B N 0.287(4) 0.479(4) -0.066(3) 0.061(4) Uani 0.097(8) 1 d D U P A 3
N3B N 0.185(3) 0.397(3) -0.007(3) 0.054(5) Uani 0.097(8) 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 1.3620(18) . ?
O1 H1 0.83 . ?
O2 C3 1.3593(19) . ?
O2 H2A 0.83 . ?
N1 C11 1.332(2) . ?
N1 C7 1.340(2) . ?
C1 C6 1.384(2) . ?
C1 C2 1.389(2) . ?
C2 C3 1.390(2) . ?
C2 H2 0.94 . ?
C3 C4 1.386(2) . ?
C4 C5 1.382(2) . ?
C4 H4 0.94 . ?
C5 C6 1.380(2) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.374(3) . ?
C7 H7 0.94 . ?
C8 C9 1.382(3) . ?
C8 H8 0.94 . ?
C9 C18 1.281(13) . ?
C9 C10 1.380(2) . ?
C9 N2A 1.495(6) . ?
C9 N2B 1.61(4) . ?
C10 C11 1.367(2) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
N2A N3A 1.233(6) . ?
N3A C12A 1.441(6) . ?
C12A C13A 1.379(5) . ?
C12A C16A 1.381(4) . ?
C13A C14A 1.386(5) . ?
C13A H13A 0.94 . ?
C14A N4A 1.302(5) . ?
C14A H14A 0.94 . ?
N4A C15A 1.324(5) . ?
C15A C16A 1.379(5) . ?
C15A H15A 0.94 . ?
C16A H16A 0.94 . ?
C12B C17 1.296(12) . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
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 1.181(16) . ?
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 117.00(14) . . ?
O1 C1 C6 118.14(14) . . ?
O1 C1 C2 121.64(13) . . ?
C6 C1 C2 120.22(14) . . ?
C1 C2 C3 120.12(13) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
O2 C3 C4 118.13(14) . . ?
O2 C3 C2 121.88(13) . . ?
C4 C3 C2 119.99(15) . . ?
C5 C4 C3 118.84(15) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C6 C5 C4 122.04(14) . . ?
C6 C5 H5 119 . . ?
C4 C5 H5 119 . . ?
C5 C6 C1 118.76(15) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C8 123.72(16) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 117.97(15) . . ?
C7 C8 H8 121 . . ?
C9 C8 H8 121 . . ?
C18 C9 C10 130.8(12) . . ?
C18 C9 C8 110.2(12) . . ?
C10 C9 C8 119.02(15) . . ?
C10 C9 N2A 112.6(2) . . ?
C8 C9 N2A 128.3(2) . . ?
C10 C9 N2B 147.9(8) . . ?
C8 C9 N2B 93.0(8) . . ?
C11 C10 C9 118.74(15) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.52(15) . . ?
N1 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
N3A N2A C9 112.9(6) . . ?
N2A N3A C12A 117.2(6) . . ?
C13A C12A C16A 118.5(3) . . ?
C13A C12A N3A 118.2(4) . . ?
C16A C12A N3A 123.3(4) . . ?
C12A C13A C14A 117.7(3) . . ?
C12A C13A H13A 121.2 . . ?
C14A C13A H13A 121.2 . . ?
N4A C14A C13A 125.1(3) . . ?
N4A C14A H14A 117.4 . . ?
C13A C14A H14A 117.4 . . ?
C14A N4A C15A 116.1(3) . . ?
N4A C15A C16A 124.6(4) . . ?
N4A C15A H15A 117.7 . . ?
C16A C15A H15A 117.7 . . ?
C15A C16A C12A 117.9(3) . . ?
C15A C16A H16A 121.1 . . ?
C12A C16A H16A 121.1 . . ?
C17 C12B C13B 114.7(11) . . ?
C17 C12B C16B 125.3(11) . . ?
C13B C12B C16B 120 . . ?
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 . . ?
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 176(3) . . ?
C17 C18 C9 167(3) . . ?
N3B N2B C9 99(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 1.94 2.7700(17) 173 1_556 yes
O2 H2A N4A 0.83 2 2.829(5) 174.4 2_666 yes
O2 H2A N4B 0.83 1.86 2.69(6) 176.5 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_BA25_270
_database_code_depnum_ccdc_archive 'CCDC 1995716'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT906_A75_BA25_270        
;
PROBLEM: Large K Value in the Analysis of Variance ......      5.626 Check 
RESPONSE: Due to diffuse scattering around Bragg peaks.
;
# end Validation Reply Form

_audit_creation_date             2019-11-07T15:24:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C16.49 H14 N3.51 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                   8.0696(2)
_cell_length_b                   9.7563(3)
_cell_length_c                   10.8866(3)
_cell_angle_alpha                93.656(2)
_cell_angle_beta                 106.798(3)
_cell_angle_gamma                113.712(3)
_cell_volume                     735.23(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    5535
_cell_measurement_theta_min      4.317
_cell_measurement_theta_max      76.316

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

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.026
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             307
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 4 3 0.1092
4 -4 -4 0.116
-2 4 5 0.0741
0 5 -5 0.001
3 3 -3 0.045
4 -1 1 0.0687
0 -5 5 0.0227
-4 1 -1 0.0879
0 -4 -4 0.1248
3 -5 -4 0.107


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

_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
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  0.71
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.863
_shelx_estimated_absorpt_T_max   0.981

#----------------------------------------------------------------------------#
#                   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      -0.0435655
_diffrn_orient_matrix_ub_12      -0.114365
_diffrn_orient_matrix_ub_13      0.0908631
_diffrn_orient_matrix_ub_21      -0.1908603
_diffrn_orient_matrix_ub_22      -0.1078992
_diffrn_orient_matrix_ub_23      -0.1093169
_diffrn_orient_matrix_ub_31      0.1048894
_diffrn_orient_matrix_ub_32      -0.0795753
_diffrn_orient_matrix_ub_33      -0.051046
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_number            12366
_diffrn_reflns_limit_h_min       -8
_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       12
_diffrn_reflns_theta_min         4.334
_diffrn_reflns_theta_max         77.124
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.948
_reflns_Friedel_coverage         0
_reflns_number_total             2962
_reflns_number_gt                2337
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_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)+(0.0695P)²+0.0834P] 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(10)
_refine_ls_number_reflns         2962
_refine_ls_number_parameters     284
_refine_ls_number_restraints     507
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1378
_refine_ls_wR_factor_gt          0.1272
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      0.983
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.18
_refine_diff_density_rms         0.037

#----------------------------------------------------------------------------#
#                   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 0.76 to 0.24 with the amount 
 of 4,4'-azopyridine in the secondary position calculated at 0.12. The
 inconsistent reflections -6 7 10, -6 9 7, -8 7 7, -5 5 10, and -5 9 8 were 
 omitted.
;

#----------------------------------------------------------------------------#
#                   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 0.16709(16) 0.15440(13) 0.31196(11) 0.0634(3) Uani 1 1 d . . . . .
H1 H 0.196978 0.175193 0.391833 0.095 Uiso 1 1 calc R U . . .
O2 O 0.81877(18) 0.21741(16) 0.43483(12) 0.0747(4) Uani 1 1 d . . . . .
H2A H 0.823263 0.254559 0.506123 0.112 Uiso 1 1 calc R U . . .
N1 N 0.2609(2) 0.24762(16) -0.42120(13) 0.0617(4) Uani 1 1 d . . . . .
C1 C 0.3179(2) 0.15135(15) 0.28177(14) 0.0512(4) Uani 1 1 d . . . . .
C2 C 0.4924(2) 0.18373(16) 0.37790(14) 0.0524(4) Uani 1 1 d . . . . .
H2 H 0.507722 0.206896 0.465868 0.063 Uiso 1 1 calc R U . . .
C3 C 0.6439(2) 0.18169(17) 0.34339(15) 0.0557(4) Uani 1 1 d . . . . .
C4 C 0.6201(3) 0.14295(19) 0.21285(16) 0.0635(4) Uani 1 1 d . . . . .
H4 H 0.719979 0.138554 0.189076 0.076 Uiso 1 1 calc R U . . .
C5 C 0.4455(3) 0.11095(19) 0.11854(16) 0.0667(5) Uani 1 1 d . . . . .
H5 H 0.429511 0.085965 0.030666 0.08 Uiso 1 1 calc R U . . .
C6 C 0.2938(3) 0.11492(18) 0.15075(15) 0.0609(4) Uani 1 1 d . . . . .
H6 H 0.177533 0.093515 0.085655 0.073 Uiso 1 1 calc R U . . .
C7 C 0.3266(3) 0.3967(2) -0.37319(19) 0.0679(4) Uani 1 1 d . . . . .
H7 H 0.376178 0.46629 -0.422751 0.082 Uiso 1 1 calc R U . . .
C8 C 0.3248(3) 0.45260(19) -0.25481(18) 0.0670(5) Uani 1 1 d . . . . .
H8 H 0.373292 0.557185 -0.224363 0.08 Uiso 1 1 calc R U . . .
C9 C 0.2488(2) 0.34878(19) -0.18240(15) 0.0572(4) Uani 1 1 d D . . . .
C10 C 0.1836(2) 0.19499(18) -0.22938(16) 0.0600(4) Uani 1 1 d . . . . .
H10 H 0.134125 0.123112 -0.181479 0.072 Uiso 1 1 calc R U . . .
C11 C 0.1930(2) 0.15024(19) -0.34764(16) 0.0609(4) Uani 1 1 d . . . . .
H11 H 0.149884 0.046424 -0.378415 0.073 Uiso 1 1 calc R U . . .
N2A N 0.2124(9) 0.3769(5) -0.0571(5) 0.0516(12) Uani 0.638(13) 1 d D U P A 1
N3A N 0.2659(5) 0.5137(5) -0.0166(5) 0.0530(11) Uani 0.638(13) 1 d D U P A 1
C12A C 0.2324(10) 0.5542(7) 0.1010(6) 0.0458(10) Uani 0.638(13) 1 d . U P A 1
C13A C 0.2856(13) 0.7060(7) 0.1467(6) 0.0566(11) Uani 0.638(13) 1 d . U P A 1
H13A H 0.34202 0.780975 0.103384 0.068 Uiso 0.638(13) 1 calc R U P A 1
C14A C 0.2524(14) 0.7430(6) 0.2584(8) 0.0612(17) Uani 0.638(13) 1 d . U P A 1
H14A H 0.289584 0.84581 0.28916 0.073 Uiso 0.638(13) 1 calc R U P A 1
N4A N 0.1731(13) 0.6455(9) 0.3248(7) 0.0569(13) Uani 0.638(13) 1 d . U P A 1
C15A C 0.1218(12) 0.5007(9) 0.2781(7) 0.0554(11) Uani 0.638(13) 1 d . U P A 1
H15A H 0.063239 0.428661 0.322923 0.066 Uiso 0.638(13) 1 calc R U P A 1
C16A C 0.1481(9) 0.4481(5) 0.1688(6) 0.0512(11) Uani 0.638(13) 1 d . U P A 1
H16A H 0.110432 0.344539 0.141359 0.061 Uiso 0.638(13) 1 calc R U P A 1
C12B C 0.2067(18) 0.5155(12) 0.1192(9) 0.049(2) Uani 0.362(13) 1 d DG U P A 2
C13B C 0.279(2) 0.6739(12) 0.1454(12) 0.063(2) Uani 0.362(13) 1 d G U P A 2
H13B H 0.336032 0.730456 0.090941 0.075 Uiso 0.362(13) 1 calc R U P A 2
C14B C 0.265(2) 0.7476(11) 0.2528(14) 0.067(4) Uani 0.362(13) 1 d G U P A 2
H14B H 0.312902 0.853582 0.270299 0.08 Uiso 0.362(13) 1 calc R U P A 2
N4B N 0.179(2) 0.6630(15) 0.3342(12) 0.066(3) Uani 0.362(13) 1 d G U P A 2
C15B C 0.1071(19) 0.5047(15) 0.3080(11) 0.058(2) Uani 0.362(13) 1 d G U P A 2
H15B H 0.049746 0.448091 0.362448 0.07 Uiso 0.362(13) 1 calc R U P A 2
C16B C 0.1210(17) 0.4309(10) 0.2006(11) 0.057(2) Uani 0.362(13) 1 d G U P A 2
H16B H 0.072875 0.324961 0.183089 0.069 Uiso 0.362(13) 1 calc R U P A 2
C17 C 0.233(3) 0.461(3) 0.0194(12) 0.057(3) Uani 0.244(17) 1 d D U P A 2
C18 C 0.254(3) 0.416(3) -0.0750(15) 0.057(4) Uani 0.244(17) 1 d D U P A 2
N2B N 0.285(3) 0.476(4) -0.068(3) 0.058(4) Uani 0.117(10) 1 d D U P A 3
N3B N 0.185(3) 0.398(3) -0.008(3) 0.055(4) Uani 0.117(10) 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 1.3600(18) . ?
O1 H1 0.82 . ?
O2 C3 1.3610(19) . ?
O2 H2A 0.82 . ?
N1 C11 1.333(2) . ?
N1 C7 1.339(2) . ?
C1 C6 1.385(2) . ?
C1 C2 1.388(2) . ?
C2 C3 1.386(2) . ?
C2 H2 0.93 . ?
C3 C4 1.384(2) . ?
C4 C5 1.381(3) . ?
C4 H4 0.93 . ?
C5 C6 1.381(3) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.373(3) . ?
C7 H7 0.93 . ?
C8 C9 1.380(3) . ?
C8 H8 0.93 . ?
C9 C18 1.284(13) . ?
C9 C10 1.379(2) . ?
C9 N2A 1.507(6) . ?
C9 N2B 1.57(4) . ?
C10 C11 1.366(2) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
N2A N3A 1.229(6) . ?
N3A C12A 1.446(7) . ?
C12A C13A 1.377(5) . ?
C12A C16A 1.378(5) . ?
C13A C14A 1.376(5) . ?
C13A H13A 0.93 . ?
C14A N4A 1.304(5) . ?
C14A H14A 0.93 . ?
N4A C15A 1.320(5) . ?
C15A C16A 1.372(5) . ?
C15A H15A 0.93 . ?
C16A H16A 0.93 . ?
C12B C17 1.288(12) . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
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 1.176(16) . ?
N2B N3B 1.239(19) . ?

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 117.12(14) . . ?
O1 C1 C6 118.09(14) . . ?
O1 C1 C2 121.88(13) . . ?
C6 C1 C2 120.03(14) . . ?
C3 C2 C1 120.28(14) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
O2 C3 C4 118.03(15) . . ?
O2 C3 C2 121.86(14) . . ?
C4 C3 C2 120.11(15) . . ?
C5 C4 C3 118.79(16) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.00(15) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.77(15) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C8 123.62(17) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 117.96(16) . . ?
C7 C8 H8 121 . . ?
C9 C8 H8 121 . . ?
C18 C9 C10 129.3(13) . . ?
C18 C9 C8 111.6(13) . . ?
C10 C9 C8 119.13(15) . . ?
C10 C9 N2A 111.8(2) . . ?
C8 C9 N2A 129.0(2) . . ?
C10 C9 N2B 147.0(7) . . ?
C8 C9 N2B 93.8(7) . . ?
C11 C10 C9 118.73(16) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.40(15) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
N3A N2A C9 112.0(7) . . ?
N2A N3A C12A 116.9(7) . . ?
C13A C12A C16A 118.4(3) . . ?
C13A C12A N3A 118.4(4) . . ?
C16A C12A N3A 123.2(4) . . ?
C14A C13A C12A 117.8(4) . . ?
C14A C13A H13A 121.1 . . ?
C12A C13A H13A 121.1 . . ?
N4A C14A C13A 125.2(3) . . ?
N4A C14A H14A 117.4 . . ?
C13A C14A H14A 117.4 . . ?
C14A N4A C15A 115.7(3) . . ?
N4A C15A C16A 125.1(4) . . ?
N4A C15A H15A 117.4 . . ?
C16A C15A H15A 117.4 . . ?
C15A C16A C12A 117.7(3) . . ?
C15A C16A H16A 121.2 . . ?
C12A C16A H16A 121.2 . . ?
C17 C12B C13B 114.3(12) . . ?
C17 C12B C16B 125.7(12) . . ?
C13B C12B C16B 120 . . ?
C12B C13B C14B 120 . . ?
C12B C13B H13B 120 . . ?
C14B C13B H13B 120 . . ?
C13B C14B N4B 120 . . ?
C13B C14B H14B 120 . . ?
N4B 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 177(3) . . ?
C17 C18 C9 170(3) . . ?
N3B N2B C9 101(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 1.96 2.7708(17) 172.5 1_556 yes
O2 H2A N4A 0.82 2.01 2.833(5) 176.2 2_666 yes
O2 H2A N4B 0.82 1.88 2.70(6) 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_A75_BA25_290
_database_code_depnum_ccdc_archive 'CCDC 1995717'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT906_A75_BA25_290        
;
PROBLEM: Large K Value in the Analysis of Variance ......      3.203 Check 
RESPONSE: Due to diffuse scattering around Bragg peaks.
;
# end Validation Reply Form

_audit_creation_date             2019-11-07T15:25:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C16.47 H14 N3.52 O2'
_chemical_formula_weight         293.21

#----------------------------------------------------------------------------#
#                   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                   8.0903(3)
_cell_length_b                   9.7624(3)
_cell_length_c                   10.8911(3)
_cell_angle_alpha                93.754(3)
_cell_angle_beta                 106.789(3)
_cell_angle_gamma                113.675(4)
_cell_volume                     737.88(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    5180
_cell_measurement_theta_min      4.341
_cell_measurement_theta_max      73.76

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

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.026
_exptl_crystal_density_diffrn    1.32
_exptl_crystal_F_000             307
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 4 3 0.1092
5 -4 -4 0.116
-2 4 5 0.0741
0 5 -5 0.001
3 3 -3 0.045
4 -1 1 0.0687
0 -5 5 0.0227
-4 1 -1 0.0879
0 -4 -4 0.1248
3 -5 -4 0.107


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

_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
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  0.648
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.864
_shelx_estimated_absorpt_T_max   0.981

#----------------------------------------------------------------------------#
#                   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      -0.0450258
_diffrn_orient_matrix_ub_12      -0.1162217
_diffrn_orient_matrix_ub_13      0.0889076
_diffrn_orient_matrix_ub_21      -0.1889378
_diffrn_orient_matrix_ub_22      -0.1070355
_diffrn_orient_matrix_ub_23      -0.1109451
_diffrn_orient_matrix_ub_31      0.1064899
_diffrn_orient_matrix_ub_32      -0.0778108
_diffrn_orient_matrix_ub_33      -0.0509262
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_number            12567
_diffrn_reflns_limit_h_min       -8
_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       11
_diffrn_reflns_theta_min         4.334
_diffrn_reflns_theta_max         77.337
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.953
_reflns_Friedel_coverage         0
_reflns_number_total             2993
_reflns_number_gt                2273
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_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)+(0.0999P)²+0.0683P] 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       0.010(2)
_refine_ls_number_reflns         2993
_refine_ls_number_parameters     284
_refine_ls_number_restraints     507
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.179
_refine_ls_wR_factor_gt          0.151
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.056

#----------------------------------------------------------------------------#
#                   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 0.77 to 0.23 with the amount 
 of 4,4'-azopyridine in the secondary position calculated at 0.15. The 
 inconsistent reflection -5 -3 9 was omitted.
;

#----------------------------------------------------------------------------#
#                   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 0.16732(19) 0.15326(16) 0.31212(12) 0.0718(4) Uani 1 1 d . . . . .
H1 H 0.197958 0.176011 0.391933 0.108 Uiso 1 1 calc R U . . .
O2 O 0.8176(2) 0.21713(19) 0.43456(14) 0.0847(5) Uani 1 1 d . . . . .
H2A H 0.822719 0.255613 0.505617 0.127 Uiso 1 1 calc R U . . .
N1 N 0.2611(2) 0.24742(19) -0.42110(16) 0.0703(4) Uani 1 1 d . . . . .
C1 C 0.3183(3) 0.15069(18) 0.28186(16) 0.0586(4) Uani 1 1 d . . . . .
C2 C 0.4918(3) 0.18304(19) 0.37804(16) 0.0598(4) Uani 1 1 d . . . . .
H2 H 0.506788 0.206031 0.465949 0.072 Uiso 1 1 calc R U . . .
C3 C 0.6438(3) 0.1813(2) 0.34365(17) 0.0632(5) Uani 1 1 d . . . . .
C4 C 0.6196(3) 0.1424(2) 0.21297(19) 0.0714(5) Uani 1 1 d . . . . .
H4 H 0.718918 0.137624 0.189073 0.086 Uiso 1 1 calc R U . . .
C5 C 0.4453(3) 0.1108(2) 0.11856(18) 0.0751(6) Uani 1 1 d . . . . .
H5 H 0.429496 0.086538 0.030626 0.09 Uiso 1 1 calc R U . . .
C6 C 0.2942(3) 0.1141(2) 0.15106(18) 0.0690(5) Uani 1 1 d . . . . .
H6 H 0.177977 0.092083 0.086064 0.083 Uiso 1 1 calc R U . . .
C7 C 0.3268(3) 0.3963(2) -0.3738(2) 0.0761(5) Uani 1 1 d . . . . .
H7 H 0.376306 0.465469 -0.423468 0.091 Uiso 1 1 calc R U . . .
C8 C 0.3251(3) 0.4526(2) -0.2552(2) 0.0752(5) Uani 1 1 d . . . . .
H8 H 0.373674 0.55717 -0.224899 0.09 Uiso 1 1 calc R U . . .
C9 C 0.2496(3) 0.3499(2) -0.18279(18) 0.0652(5) Uani 1 1 d D . . . .
C10 C 0.1844(3) 0.1963(2) -0.22957(18) 0.0684(5) Uani 1 1 d . . . . .
H10 H 0.135209 0.124877 -0.181441 0.082 Uiso 1 1 calc R U . . .
C11 C 0.1932(3) 0.1507(2) -0.34736(19) 0.0696(5) Uani 1 1 d . . . . .
H11 H 0.149504 0.046805 -0.377951 0.083 Uiso 1 1 calc R U . . .
N2A N 0.2127(10) 0.3784(6) -0.0576(6) 0.0576(14) Uani 0.608(14) 1 d D U P A 1
N3A N 0.2655(7) 0.5136(6) -0.0161(6) 0.0607(12) Uani 0.608(14) 1 d D U P A 1
C12A C 0.2331(12) 0.5534(8) 0.1018(7) 0.0525(11) Uani 0.608(14) 1 d . U P A 1
C13A C 0.2841(15) 0.7055(8) 0.1484(8) 0.0643(13) Uani 0.608(14) 1 d . U P A 1
H13A H 0.340707 0.781332 0.106069 0.077 Uiso 0.608(14) 1 calc R U P A 1
C14A C 0.2481(16) 0.7408(7) 0.2600(9) 0.0669(17) Uani 0.608(14) 1 d . U P A 1
H14A H 0.282835 0.843107 0.290779 0.08 Uiso 0.608(14) 1 calc R U P A 1
N4A N 0.1699(15) 0.6431(10) 0.3251(8) 0.0647(16) Uani 0.608(14) 1 d . U P A 1
C15A C 0.1217(14) 0.5001(10) 0.2781(8) 0.0642(13) Uani 0.608(14) 1 d . U P A 1
H15A H 0.064095 0.427351 0.32257 0.077 Uiso 0.608(14) 1 calc R U P A 1
C16A C 0.1492(11) 0.4486(7) 0.1686(7) 0.0593(14) Uani 0.608(14) 1 d . U P A 1
H16A H 0.111685 0.345125 0.140746 0.071 Uiso 0.608(14) 1 calc R U P A 1
C12B C 0.2048(19) 0.5127(13) 0.1161(10) 0.059(2) Uani 0.392(14) 1 d DG U P A 2
C13B C 0.280(2) 0.6713(13) 0.1424(12) 0.068(3) Uani 0.392(14) 1 d G U P A 2
H13B H 0.337488 0.726677 0.087467 0.082 Uiso 0.392(14) 1 calc R U P A 2
C14B C 0.270(2) 0.7470(11) 0.2507(14) 0.073(3) Uani 0.392(14) 1 d G U P A 2
H14B H 0.321031 0.853035 0.268275 0.087 Uiso 0.392(14) 1 calc R U P A 2
N4B N 0.185(2) 0.6641(16) 0.3327(12) 0.071(3) Uani 0.392(14) 1 d G U P A 2
C15B C 0.110(2) 0.5056(15) 0.3064(12) 0.067(2) Uani 0.392(14) 1 d G U P A 2
H15B H 0.052458 0.450183 0.361341 0.08 Uiso 0.392(14) 1 calc R U P A 2
C16B C 0.1194(18) 0.4299(11) 0.1981(12) 0.062(2) Uani 0.392(14) 1 d G U P A 2
H16B H 0.068914 0.323821 0.180534 0.075 Uiso 0.392(14) 1 calc R U P A 2
C17 C 0.234(3) 0.461(4) 0.0185(15) 0.064(3) Uani 0.234(17) 1 d D U P A 2
C18 C 0.255(4) 0.414(4) -0.0775(18) 0.063(4) Uani 0.234(17) 1 d D U P A 2
N2B N 0.280(3) 0.477(3) -0.069(2) 0.061(3) Uani 0.152(10) 1 d D U P A 3
N3B N 0.189(3) 0.395(4) -0.005(3) 0.065(4) Uani 0.152(10) 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 1.363(2) . ?
O1 H1 0.82 . ?
O2 C3 1.354(2) . ?
O2 H2A 0.82 . ?
N1 C11 1.333(3) . ?
N1 C7 1.336(3) . ?
C1 C6 1.383(2) . ?
C1 C2 1.385(2) . ?
C2 C3 1.390(3) . ?
C2 H2 0.93 . ?
C3 C4 1.384(3) . ?
C4 C5 1.383(3) . ?
C4 H4 0.93 . ?
C5 C6 1.378(3) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.376(3) . ?
C7 H7 0.93 . ?
C8 C9 1.375(3) . ?
C8 H8 0.93 . ?
C9 C18 1.249(14) . ?
C9 C10 1.377(3) . ?
C9 N2A 1.509(7) . ?
C9 N2B 1.58(3) . ?
C10 C11 1.361(3) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
N2A N3A 1.219(7) . ?
N3A C12A 1.442(9) . ?
C12A C16A 1.364(6) . ?
C12A C13A 1.386(6) . ?
C13A C14A 1.382(7) . ?
C13A H13A 0.93 . ?
C14A N4A 1.295(6) . ?
C14A H14A 0.93 . ?
N4A C15A 1.311(6) . ?
C15A C16A 1.375(7) . ?
C15A H15A 0.93 . ?
C16A H16A 0.93 . ?
C12B C17 1.268(13) . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
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 1.201(18) . ?
N2B N3B 1.254(18) . ?

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 117.22(17) . . ?
O1 C1 C6 118.10(16) . . ?
O1 C1 C2 121.76(15) . . ?
C6 C1 C2 120.15(17) . . ?
C1 C2 C3 120.26(16) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
O2 C3 C4 118.13(17) . . ?
O2 C3 C2 122.02(16) . . ?
C4 C3 C2 119.85(18) . . ?
C5 C4 C3 118.89(18) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C6 C5 C4 121.89(17) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 118.93(18) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.3(2) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C9 C8 C7 118.18(18) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C18 C9 C8 112.5(16) . . ?
C18 C9 C10 128.4(16) . . ?
C8 C9 C10 119.00(18) . . ?
C8 C9 N2A 129.2(3) . . ?
C10 C9 N2A 111.7(3) . . ?
C8 C9 N2B 94.3(6) . . ?
C10 C9 N2B 146.7(6) . . ?
C11 C10 C9 118.91(19) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N1 C11 C10 123.33(18) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
N3A N2A C9 112.7(8) . . ?
N2A N3A C12A 117.3(8) . . ?
C16A C12A C13A 117.7(4) . . ?
C16A C12A N3A 123.5(5) . . ?
C13A C12A N3A 118.7(5) . . ?
C14A C13A C12A 117.8(4) . . ?
C14A C13A H13A 121.1 . . ?
C12A C13A H13A 121.1 . . ?
N4A C14A C13A 125.3(4) . . ?
N4A C14A H14A 117.3 . . ?
C13A C14A H14A 117.3 . . ?
C14A N4A C15A 115.5(4) . . ?
N4A C15A C16A 125.4(5) . . ?
N4A C15A H15A 117.3 . . ?
C16A C15A H15A 117.3 . . ?
C12A C16A C15A 118.2(4) . . ?
C12A C16A H16A 120.9 . . ?
C15A C16A H16A 120.9 . . ?
C17 C12B C13B 112.5(14) . . ?
C17 C12B C16B 127.4(14) . . ?
C13B C12B C16B 120 . . ?
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 177(2) . . ?
C17 C18 C9 171(4) . . ?
N3B N2B C9 100(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 1.95 2.771(2) 173.7 1_556 yes
O2 H2A N4A 0.82 2.01 2.827(6) 177 2_666 yes
O2 H2A N4B 0.82 1.91 2.73(6) 175.8 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_BA25_230
_database_code_depnum_ccdc_archive 'CCDC 1995714'
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT906_A75_BA25_230        
;
PROBLEM: Large K Value in the Analysis of Variance ......      4.226 Check 
RESPONSE: Due to diffuse scattering around Bragg peaks.
;
# end Validation Reply Form

_audit_creation_date             2019-11-07T15:21:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C16.51 H14 N3.49 O2'
_chemical_formula_weight         293.36

#----------------------------------------------------------------------------#
#                   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                   8.03328(18)
_cell_length_b                   9.7401(2)
_cell_length_c                   10.8685(2)
_cell_angle_alpha                93.4267(17)
_cell_angle_beta                 106.8463(19)
_cell_angle_gamma                113.829(2)
_cell_volume                     729.19(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    6099
_cell_measurement_theta_min      4.326
_cell_measurement_theta_max      74.563

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

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.026
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             307
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 4 3 0.1092
4 0 0 0.0687
0 5 -5 0.001
-2 5 4 0.0741
3 -5 -4 0.107
-4 0 0 0.0879
3 3 -3 0.045
0 -5 5 0.0227
4 -4 -4 0.116
0 -4 -4 0.1248


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

_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
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  0.722
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.862
_shelx_estimated_absorpt_T_max   0.981

#----------------------------------------------------------------------------#
#                   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      -0.0242743
_diffrn_orient_matrix_ub_12      -0.1049263
_diffrn_orient_matrix_ub_13      0.1005706
_diffrn_orient_matrix_ub_21      -0.1947038
_diffrn_orient_matrix_ub_22      -0.1187566
_diffrn_orient_matrix_ub_23      -0.1004155
_diffrn_orient_matrix_ub_31      0.1065049
_diffrn_orient_matrix_ub_32      -0.0778151
_diffrn_orient_matrix_ub_33      -0.0516645
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_number            12806
_diffrn_reflns_limit_h_min       -8
_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       12
_diffrn_reflns_theta_min         4.34
_diffrn_reflns_theta_max         77.357
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.951
_reflns_Friedel_coverage         0
_reflns_number_total             2949
_reflns_number_gt                2433
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_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)+(0.0749P)²+0.0927P] 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       0.0050(11)
_refine_ls_number_reflns         2949
_refine_ls_number_parameters     284
_refine_ls_number_restraints     507
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1357
_refine_ls_wR_factor_gt          0.1279
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      0.968
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   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 0.74 to 0.26 with the amount 
 of 4,4'-azopyridine in the secondary position calculated at 0.08. The 
 inconsistent reflections -6 9 7, -8 7 7, -6 8 8, -5 8 9, and -5 7 9 were 
 omitted.
;

#----------------------------------------------------------------------------#
#                   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 0.16619(15) 0.15638(12) 0.31178(10) 0.0545(3) Uani 1 1 d . . . . .
H1 H 0.196309 0.176599 0.392741 0.082 Uiso 1 1 calc R U . . .
O2 O 0.82089(16) 0.21815(15) 0.43527(11) 0.0636(3) Uani 1 1 d . . . . .
H2A H 0.824619 0.254046 0.507769 0.095 Uiso 1 1 calc R U . . .
N1 N 0.26157(18) 0.24836(15) -0.42102(13) 0.0538(3) Uani 1 1 d . . . . .
C1 C 0.3176(2) 0.15302(15) 0.28155(13) 0.0445(3) Uani 1 1 d . . . . .
C2 C 0.4927(2) 0.18507(15) 0.37816(13) 0.0455(3) Uani 1 1 d . . . . .
H2 H 0.508181 0.208643 0.467125 0.055 Uiso 1 1 calc R U . . .
C3 C 0.6450(2) 0.18237(16) 0.34359(14) 0.0483(3) Uani 1 1 d . . . . .
C4 C 0.6209(2) 0.14335(18) 0.21265(15) 0.0550(4) Uani 1 1 d . . . . .
H4 H 0.722184 0.138545 0.188692 0.066 Uiso 1 1 calc R U . . .
C5 C 0.4451(3) 0.11161(17) 0.11785(15) 0.0567(4) Uani 1 1 d . . . . .
H5 H 0.428778 0.086312 0.028945 0.068 Uiso 1 1 calc R U . . .
C6 C 0.2931(2) 0.11607(17) 0.15024(14) 0.0526(4) Uani 1 1 d . . . . .
H6 H 0.17499 0.094413 0.084386 0.063 Uiso 1 1 calc R U . . .
C7 C 0.3265(2) 0.39751(19) -0.37244(17) 0.0593(4) Uani 1 1 d . . . . .
H7 H 0.376644 0.468727 -0.422365 0.071 Uiso 1 1 calc R U . . .
C8 C 0.3240(2) 0.45224(18) -0.25363(17) 0.0578(4) Uani 1 1 d . . . . .
H8 H 0.372914 0.557953 -0.222474 0.069 Uiso 1 1 calc R U . . .
C9 C 0.2473(2) 0.34698(17) -0.18149(15) 0.0496(4) Uani 1 1 d D . . . .
C10 C 0.1828(2) 0.19292(17) -0.22904(15) 0.0509(4) Uani 1 1 d . . . . .
H10 H 0.132713 0.119364 -0.18085 0.061 Uiso 1 1 calc R U . . .
C11 C 0.1933(2) 0.14946(17) -0.34784(15) 0.0522(4) Uani 1 1 d . . . . .
H11 H 0.150172 0.044618 -0.379321 0.063 Uiso 1 1 calc R U . . .
N2A N 0.2115(8) 0.3762(5) -0.0573(4) 0.0433(10) Uani 0.667(13) 1 d D U P A 1
N3A N 0.2662(5) 0.5145(5) -0.0166(4) 0.0448(9) Uani 0.667(13) 1 d D U P A 1
C12A C 0.2324(9) 0.5544(6) 0.1001(5) 0.0387(9) Uani 0.667(13) 1 d . U P A 1
C13A C 0.2868(11) 0.7072(6) 0.1462(6) 0.0481(10) Uani 0.667(13) 1 d . U P A 1
H13A H 0.34474 0.783554 0.102691 0.058 Uiso 0.667(13) 1 calc R U P A 1
C14A C 0.2526(13) 0.7436(6) 0.2592(7) 0.0522(15) Uani 0.667(13) 1 d . U P A 1
H14A H 0.290011 0.847475 0.290428 0.063 Uiso 0.667(13) 1 calc R U P A 1
N4A N 0.1725(12) 0.6449(8) 0.3253(6) 0.0478(11) Uani 0.667(13) 1 d . U P A 1
C15A C 0.1204(10) 0.4994(7) 0.2787(6) 0.0467(10) Uani 0.667(13) 1 d . U P A 1
H15A H 0.060796 0.426228 0.324097 0.056 Uiso 0.667(13) 1 calc R U P A 1
C16A C 0.1469(8) 0.4475(5) 0.1688(5) 0.0428(10) Uani 0.667(13) 1 d . U P A 1
H16A H 0.108258 0.342653 0.140955 0.051 Uiso 0.667(13) 1 calc R U P A 1
C12B C 0.2093(18) 0.5197(12) 0.1218(9) 0.041(2) Uani 0.333(13) 1 d DG U P A 2
C13B C 0.280(2) 0.6782(12) 0.1462(12) 0.053(2) Uani 0.333(13) 1 d G U P A 2
H13B H 0.338175 0.735178 0.090677 0.063 Uiso 0.333(13) 1 calc R U P A 2
C14B C 0.265(3) 0.7526(10) 0.2527(15) 0.055(3) Uani 0.333(13) 1 d G U P A 2
H14B H 0.312662 0.859763 0.269192 0.066 Uiso 0.333(13) 1 calc R U P A 2
N4B N 0.179(3) 0.6684(15) 0.3348(13) 0.056(3) Uani 0.333(13) 1 d G U P A 2
C15B C 0.1081(19) 0.5098(15) 0.3103(11) 0.052(2) Uani 0.333(13) 1 d G U P A 2
H15B H 0.050024 0.452895 0.365852 0.062 Uiso 0.333(13) 1 calc R U P A 2
C16B C 0.1234(16) 0.4355(10) 0.2038(11) 0.050(2) Uani 0.333(13) 1 d G U P A 2
H16B H 0.075535 0.328307 0.187337 0.06 Uiso 0.333(13) 1 calc R U P A 2
C17 C 0.2333(18) 0.463(2) 0.0191(11) 0.050(3) Uani 0.257(15) 1 d D U P A 2
C18 C 0.254(2) 0.415(2) -0.0753(13) 0.049(3) Uani 0.257(15) 1 d D U P A 2
N2B N 0.291(4) 0.486(4) -0.060(3) 0.056(5) Uani 0.079(7) 1 d D U P A 3
N3B N 0.185(4) 0.394(3) -0.010(3) 0.050(5) Uani 0.079(7) 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 1.3602(18) . ?
O1 H1 0.83 . ?
O2 C3 1.3624(18) . ?
O2 H2A 0.83 . ?
N1 C11 1.334(2) . ?
N1 C7 1.341(2) . ?
C1 C6 1.387(2) . ?
C1 C2 1.389(2) . ?
C2 C3 1.389(2) . ?
C2 H2 0.94 . ?
C3 C4 1.387(2) . ?
C4 C5 1.385(2) . ?
C4 H4 0.94 . ?
C5 C6 1.381(2) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.376(2) . ?
C7 H7 0.94 . ?
C8 C9 1.382(2) . ?
C8 H8 0.94 . ?
C9 C18 1.274(12) . ?
C9 C10 1.382(2) . ?
C9 N2A 1.493(5) . ?
C9 N2B 1.68(4) . ?
C10 C11 1.371(2) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
N2A N3A 1.241(6) . ?
N3A C12A 1.435(6) . ?
C12A C13A 1.384(4) . ?
C12A C16A 1.387(4) . ?
C13A C14A 1.389(4) . ?
C13A H13A 0.94 . ?
C14A N4A 1.306(5) . ?
C14A H14A 0.94 . ?
N4A C15A 1.323(5) . ?
C15A C16A 1.376(5) . ?
C15A H15A 0.94 . ?
C16A H16A 0.94 . ?
C12B C17 1.314(11) . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
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 1.182(16) . ?
N2B N3B 1.24(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 117.14(14) . . ?
O1 C1 C6 118.16(13) . . ?
O1 C1 C2 121.70(12) . . ?
C6 C1 C2 120.14(13) . . ?
C1 C2 C3 120.13(13) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
O2 C3 C4 118.04(14) . . ?
O2 C3 C2 121.83(13) . . ?
C4 C3 C2 120.13(14) . . ?
C5 C4 C3 118.81(15) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C6 C5 C4 121.86(14) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 118.90(14) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.71(15) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 117.97(14) . . ?
C7 C8 H8 121 . . ?
C9 C8 H8 121 . . ?
C18 C9 C8 110.3(10) . . ?
C18 C9 C10 130.6(10) . . ?
C8 C9 C10 119.07(14) . . ?
C8 C9 N2A 128.0(2) . . ?
C10 C9 N2A 112.8(2) . . ?
C8 C9 N2B 92.2(8) . . ?
C10 C9 N2B 148.7(8) . . ?
C11 C10 C9 118.73(14) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.35(14) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
N3A N2A C9 112.5(6) . . ?
N2A N3A C12A 116.9(6) . . ?
C13A C12A C16A 118.2(3) . . ?
C13A C12A N3A 118.4(4) . . ?
C16A C12A N3A 123.4(3) . . ?
C12A C13A C14A 117.6(3) . . ?
C12A C13A H13A 121.2 . . ?
C14A C13A H13A 121.2 . . ?
N4A C14A C13A 125.2(3) . . ?
N4A C14A H14A 117.4 . . ?
C13A C14A H14A 117.4 . . ?
C14A N4A C15A 116.2(3) . . ?
N4A C15A C16A 124.8(3) . . ?
N4A C15A H15A 117.6 . . ?
C16A C15A H15A 117.6 . . ?
C15A C16A C12A 118.1(3) . . ?
C15A C16A H16A 120.9 . . ?
C12A C16A H16A 120.9 . . ?
C17 C12B C13B 114.4(9) . . ?
C17 C12B C16B 125.6(9) . . ?
C13B C12B C16B 120 . . ?
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 . . ?
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 178(2) . . ?
C17 C18 C9 170(2) . . ?
N3B N2B C9 93(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 0.83 1.94 2.7691(16) 172.3 1_556 yes
O2 H2A N4A 0.83 2 2.829(5) 174.7 2_666 yes
O2 H2A N4B 0.83 1.84 2.67(6) 177.4 2_666 yes

