# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_diclofenac4-4'-BPE
_database_code_depnum_ccdc_archive 'CCDC 1909029'
loop_
_audit_author_name
_audit_author_address
'Daniel K. Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-04-09 deposited with the CCDC.	2019-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT250_diclofenacBPE       
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        3.7 Note  
RESPONSE: This is related to a disorder interstitial toluene molecule.
;
_vrf_PLAT911_diclofenac4-4'-BPE  
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
RESPONSE: These reflections were not collected using Omega scans only.
;
# end Validation Reply Form

_audit_creation_date             2018-04-03T10:33:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C47 H40 Cl4 N4 O4'
_chemical_formula_weight         866.63

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.763(2)
_cell_length_b                   7.0061(8)
_cell_length_c                   30.454(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.447(2)
_cell_angle_gamma                90
_cell_volume                     4159.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8456
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.13

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

_exptl_crystal_description       blade
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.485
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.095
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             1800

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

_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.
_shelx_estimated_absorpt_T_min   0.854
_shelx_estimated_absorpt_T_max   0.969

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_number            23563
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.356
_diffrn_reflns_theta_max         27.165
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_number_total             4604
_reflns_number_gt                3966
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

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

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

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

_refine_special_details          
;
 Carbon atoms C21 < C27 of the interstitial toluene molecule were positionally
 disorder as well as centered about an inversion center. The carbon atoms sites
 were split into A and B components and were allowed to free refine to a sum 
 of 0.5.  The site occupancies of the A and B sites were 0.18, and 0.32, 
 respectively.  Due to the inversion center and positional disorder PART -1 and
 PART -2 were applied, as well as AFIX 66, SIMU, DELU, and free variable DFIX 
 constraints and restraints to help model the disorder.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0320P)²+4.9478P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4604
_refine_ls_number_parameters     345
_refine_ls_number_restraints     260
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0779
_refine_ls_wR_factor_gt          0.0738
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.046

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.38703(2) 1.08953(5) 0.29241(2) 0.02153(9) Uani 1 d . .
Cl2 Cl 0.55765(2) 0.55264(5) 0.37680(2) 0.02039(9) Uani 1 d . .
O1 O 0.38648(5) 0.39199(15) 0.38961(4) 0.0228(2) Uani 1 d . .
H1 H 0.399772 0.288045 0.401817 0.034 Uiso 1 calc . .
O2 O 0.28220(6) 0.27375(17) 0.39307(4) 0.0341(3) Uani 1 d . .
N1 N 0.42095(6) 0.70893(18) 0.33658(4) 0.0172(2) Uani 1 d . .
H1A H 0.4279(9) 0.633(3) 0.3577(6) 0.026 Uiso 1 d . .
N2 N 0.43560(7) 1.07709(17) 0.42639(4) 0.0216(3) Uani 1 d . .
C1 C 0.54409(7) 0.77448(19) 0.35074(4) 0.0162(3) Uani 1 d . .
C2 C 0.47696(7) 0.82508(19) 0.33241(4) 0.0151(3) Uani 1 d . .
C3 C 0.46869(7) 1.0065(2) 0.31257(4) 0.0164(3) Uani 1 d . .
C4 C 0.52394(7) 1.1247(2) 0.30981(5) 0.0192(3) Uani 1 d . .
H4 H 0.516892 1.244895 0.295337 0.023 Uiso 1 calc . .
C5 C 0.58966(7) 1.0672(2) 0.32826(5) 0.0210(3) Uani 1 d . .
H5 H 0.627614 1.148214 0.326392 0.025 Uiso 1 calc . .
C6 C 0.60017(7) 0.8920(2) 0.34940(5) 0.0189(3) Uani 1 d . .
H6 H 0.644914 0.853221 0.362711 0.023 Uiso 1 calc . .
C7 C 0.37663(7) 0.63276(19) 0.29927(5) 0.0150(3) Uani 1 d . .
C8 C 0.31375(7) 0.55487(19) 0.30607(5) 0.0158(3) Uani 1 d . .
C9 C 0.27091(7) 0.4729(2) 0.27037(5) 0.0190(3) Uani 1 d . .
H9 H 0.228727 0.417625 0.274946 0.023 Uiso 1 calc . .
C10 C 0.28859(7) 0.4700(2) 0.22806(5) 0.0203(3) Uani 1 d . .
H10 H 0.258751 0.413513 0.203928 0.024 Uiso 1 calc . .
C11 C 0.35013(7) 0.5504(2) 0.22141(5) 0.0196(3) Uani 1 d . .
H11 H 0.362325 0.550197 0.192507 0.023 Uiso 1 calc . .
C12 C 0.39411(7) 0.6314(2) 0.25677(5) 0.0180(3) Uani 1 d . .
H12 H 0.436267 0.686076 0.251962 0.022 Uiso 1 calc . .
C13 C 0.29184(7) 0.5617(2) 0.35141(5) 0.0191(3) Uani 1 d . .
H13A H 0.241117 0.562753 0.34757 0.023 Uiso 1 calc . .
H13B H 0.308783 0.681448 0.366623 0.023 Uiso 1 calc . .
C14 C 0.31887(7) 0.3933(2) 0.38030(5) 0.0199(3) Uani 1 d . .
C15 C 0.50308(8) 1.0432(2) 0.43500(5) 0.0227(3) Uani 1 d . .
H15 H 0.533416 1.13579 0.426315 0.027 Uiso 1 calc . .
C16 C 0.53055(8) 0.8792(2) 0.45599(5) 0.0228(3) Uani 1 d . .
H16 H 0.578832 0.860894 0.461596 0.027 Uiso 1 calc . .
C17 C 0.48726(8) 0.7411(2) 0.46885(5) 0.0222(3) Uani 1 d . .
C18 C 0.41677(8) 0.7762(2) 0.45923(5) 0.0246(3) Uani 1 d . .
H18 H 0.385178 0.685151 0.467057 0.029 Uiso 1 calc . .
C19 C 0.39328(8) 0.9442(2) 0.43826(5) 0.0244(3) Uani 1 d . .
H19 H 0.34523 0.966288 0.432023 0.029 Uiso 1 calc . .
C20 C 0.51747(8) 0.5695(2) 0.49222(5) 0.0240(3) Uani 1 d . .
H20 H 0.56599 0.557484 0.496493 0.029 Uiso 1 calc . .
C21A C 0.2395(11) 0.8557(17) 0.4923(6) 0.057(2) Uani 0.179(4) d A -1
H21A H 0.219713 0.964436 0.476578 0.068 Uiso 0.179(4) calc A -1
C22A C 0.2706(12) 0.873(2) 0.5366(6) 0.056(3) Uani 0.179(4) d A -1
H22A H 0.27197 0.993248 0.550999 0.068 Uiso 0.179(4) calc A -1
C23A C 0.2995(10) 0.714(3) 0.5596(4) 0.056(3) Uani 0.179(4) d A -1
H23A H 0.320734 0.725369 0.589833 0.067 Uiso 0.179(4) calc A -1
C24A C 0.2974(7) 0.537(2) 0.5385(4) 0.043(2) Uani 0.179(4) d A -1
H24A H 0.317241 0.428676 0.554246 0.052 Uiso 0.179(4) calc A -1
C25A C 0.2664(6) 0.5203(16) 0.4943(4) 0.049(2) Uani 0.179(4) d A -1
H25A H 0.264983 0.399861 0.479825 0.058 Uiso 0.179(4) calc A -1
C26A C 0.2374(8) 0.6794(19) 0.4712(3) 0.051(2) Uani 0.179(4) d A -1
C27A C 0.1915(11) 0.766(3) 0.4313(6) 0.074(4) Uani 0.179(4) d A -1
H27A H 0.207171 0.895682 0.426251 0.112 Uiso 0.179(4) calc A -1
H27B H 0.144148 0.770835 0.437113 0.112 Uiso 0.179(4) calc A -1
H27C H 0.193403 0.687704 0.404923 0.112 Uiso 0.179(4) calc A -1
C21B C 0.2554(5) 0.6018(9) 0.5019(3) 0.0452(15) Uani 0.321(4) d A -2
C22B C 0.2206(6) 0.6321(12) 0.4590(3) 0.0539(18) Uani 0.321(4) d A -2
H22B H 0.210022 0.5273 0.439279 0.065 Uiso 0.321(4) calc A -2
C23B C 0.2013(5) 0.8158(15) 0.4449(2) 0.061(2) Uani 0.321(4) d A -2
H23B H 0.177456 0.836514 0.415588 0.074 Uiso 0.321(4) calc A -2
C24B C 0.2167(5) 0.9692(10) 0.4738(3) 0.066(2) Uani 0.321(4) d A -2
H24B H 0.203523 1.094732 0.464153 0.079 Uiso 0.321(4) calc A -2
C25B C 0.2516(4) 0.9389(9) 0.5167(3) 0.0643(19) Uani 0.321(4) d A -2
H25B H 0.262157 1.043738 0.536411 0.077 Uiso 0.321(4) calc A -2
C26B C 0.2709(4) 0.7552(12) 0.5308(2) 0.0511(15) Uani 0.321(4) d A -2
H26B H 0.294724 0.734525 0.560103 0.061 Uiso 0.321(4) calc A -2
C27B C 0.2841(5) 0.4262(14) 0.5222(3) 0.072(3) Uani 0.321(4) d A -2
H27D H 0.320931 0.456336 0.546926 0.108 Uiso 0.321(4) calc A -2
H27E H 0.302746 0.349923 0.499971 0.108 Uiso 0.321(4) calc A -2
H27F H 0.248174 0.353565 0.533407 0.108 Uiso 0.321(4) calc 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
Cl1 C3 1.7306(14) . ?
Cl2 C1 1.7458(14) . ?
O1 C14 1.3197(17) . ?
O1 H1 0.84 . ?
O2 C14 1.2128(18) . ?
N1 C2 1.3963(17) . ?
N1 C7 1.4200(17) . ?
N1 H1A 0.829(19) . ?
N2 C15 1.337(2) . ?
N2 C19 1.340(2) . ?
C1 C6 1.3868(19) . ?
C1 C2 1.3978(19) . ?
C2 C3 1.4051(19) . ?
C3 C4 1.3841(19) . ?
C4 C5 1.388(2) . ?
C4 H4 0.95 . ?
C5 C6 1.385(2) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C12 1.3932(19) . ?
C7 C8 1.4034(18) . ?
C8 C9 1.388(2) . ?
C8 C13 1.5140(19) . ?
C9 C10 1.389(2) . ?
C9 H9 0.95 . ?
C10 C11 1.385(2) . ?
C10 H10 0.95 . ?
C11 C12 1.389(2) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
C13 C14 1.5152(19) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C15 C16 1.382(2) . ?
C15 H15 0.95 . ?
C16 C17 1.390(2) . ?
C16 H16 0.95 . ?
C17 C18 1.398(2) . ?
C17 C20 1.472(2) . ?
C18 C19 1.382(2) . ?
C18 H18 0.95 . ?
C19 H19 0.95 . ?
C20 C20 1.326(3) 5_666 ?
C20 H20 0.95 . ?
C21A C22A 1.39 . ?
C21A C26A 1.39 . ?
C21A H21A 0.95 . ?
C22A C23A 1.39 . ?
C22A H22A 0.95 . ?
C23A C24A 1.39 . ?
C23A H23A 0.95 . ?
C24A C25A 1.39 . ?
C24A H24A 0.95 . ?
C25A C26A 1.39 . ?
C25A H25A 0.95 . ?
C26A C27A 1.519(16) . ?
C27A H27A 0.98 . ?
C27A H27B 0.98 . ?
C27A H27C 0.98 . ?
C21B C22B 1.39 . ?
C21B C26B 1.39 . ?
C21B C27B 1.450(10) . ?
C22B C23B 1.39 . ?
C22B H22B 0.95 . ?
C23B C24B 1.39 . ?
C23B H23B 0.95 . ?
C24B C25B 1.39 . ?
C24B H24B 0.95 . ?
C25B C26B 1.39 . ?
C25B H25B 0.95 . ?
C26B H26B 0.95 . ?
C27B H27D 0.98 . ?
C27B H27E 0.98 . ?
C27B H27F 0.98 . ?

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
C14 O1 H1 109.5 . . ?
C2 N1 C7 122.70(11) . . ?
C2 N1 H1A 114.4(12) . . ?
C7 N1 H1A 112.2(12) . . ?
C15 N2 C19 118.03(13) . . ?
C6 C1 C2 123.25(13) . . ?
C6 C1 Cl2 118.57(11) . . ?
C2 C1 Cl2 118.18(10) . . ?
N1 C2 C1 122.03(12) . . ?
N1 C2 C3 121.88(12) . . ?
C1 C2 C3 115.91(12) . . ?
C4 C3 C2 122.02(12) . . ?
C4 C3 Cl1 118.44(11) . . ?
C2 C3 Cl1 119.51(10) . . ?
C3 C4 C5 119.78(13) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.30(13) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 118.69(13) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
C12 C7 C8 119.67(12) . . ?
C12 C7 N1 122.10(12) . . ?
C8 C7 N1 118.22(12) . . ?
C9 C8 C7 119.09(13) . . ?
C9 C8 C13 119.90(12) . . ?
C7 C8 C13 121.00(12) . . ?
C8 C9 C10 121.23(13) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 119.36(13) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 120.35(14) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 120.26(13) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?
C8 C13 C14 112.25(12) . . ?
C8 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
C8 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
O2 C14 O1 124.29(14) . . ?
O2 C14 C13 123.48(13) . . ?
O1 C14 C13 112.23(12) . . ?
N2 C15 C16 122.80(15) . . ?
N2 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C15 C16 C17 119.73(15) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 117.19(14) . . ?
C16 C17 C20 119.01(14) . . ?
C18 C17 C20 123.79(14) . . ?
C19 C18 C17 119.63(15) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
N2 C19 C18 122.61(15) . . ?
N2 C19 H19 118.7 . . ?
C18 C19 H19 118.7 . . ?
C20 C20 C17 125.37(19) 5_666 . ?
C20 C20 H20 117.3 5_666 . ?
C17 C20 H20 117.3 . . ?
C22A C21A C26A 120 . . ?
C22A C21A H21A 120 . . ?
C26A C21A H21A 120 . . ?
C21A C22A C23A 120 . . ?
C21A C22A H22A 120 . . ?
C23A C22A H22A 120 . . ?
C24A C23A C22A 120 . . ?
C24A C23A H23A 120 . . ?
C22A C23A H23A 120 . . ?
C25A C24A C23A 120 . . ?
C25A C24A H24A 120 . . ?
C23A C24A H24A 120 . . ?
C24A C25A C26A 120 . . ?
C24A C25A H25A 120 . . ?
C26A C25A H25A 120 . . ?
C25A C26A C21A 120 . . ?
C25A C26A C27A 150.2(13) . . ?
C21A C26A C27A 89.0(12) . . ?
C26A C27A H27A 109.5 . . ?
C26A C27A H27B 109.5 . . ?
H27A C27A H27B 109.5 . . ?
C26A C27A H27C 109.5 . . ?
H27A C27A H27C 109.5 . . ?
H27B C27A H27C 109.5 . . ?
C22B C21B C26B 120 . . ?
C22B C21B C27B 129.0(7) . . ?
C26B C21B C27B 110.9(7) . . ?
C21B C22B C23B 120 . . ?
C21B C22B H22B 120 . . ?
C23B C22B H22B 120 . . ?
C22B C23B C24B 120 . . ?
C22B C23B H23B 120 . . ?
C24B C23B H23B 120 . . ?
C25B C24B C23B 120 . . ?
C25B C24B H24B 120 . . ?
C23B C24B H24B 120 . . ?
C24B C25B C26B 120 . . ?
C24B C25B H25B 120 . . ?
C26B C25B H25B 120 . . ?
C25B C26B C21B 120 . . ?
C25B C26B H26B 120 . . ?
C21B C26B H26B 120 . . ?
C21B C27B H27D 109.5 . . ?
C21B C27B H27E 109.5 . . ?
H27D C27B H27E 109.5 . . ?
C21B C27B H27F 109.5 . . ?
H27D C27B H27F 109.5 . . ?
H27E C27B H27F 109.5 . . ?

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
N1 H1A O1 0.829(19) 2.172(19) 2.8919(16) 145.1(16) .
O1 H1 N2 0.84 1.75 2.5900(16) 174.4 1_545

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_diclofenac4-4'-AP
_database_code_depnum_ccdc_archive 'CCDC 1909031'
loop_
_audit_author_name
_audit_author_address
'Daniel K. Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-04-09 deposited with the CCDC.	2019-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT411_diclofenac4-4'-AP   
;
PROBLEM: Short Inter H...H Contact  H5       ..H23B             2.11 Ang.  
RESPONSE: Due to the positional disorder of the 4,4'-azopyridine molecule.
;
# end Validation Reply Form

_audit_creation_date             2018-08-08T11:33:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C24 H19 Cl2 N5 O2'
_chemical_formula_weight         480.34

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   29.485(5)
_cell_length_b                   4.6618(7)
_cell_length_c                   34.442(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.016(2)
_cell_angle_gamma                90
_cell_volume                     4722.6(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6742
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      26.65

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

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.075
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             1984

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

_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6516
_shelx_estimated_absorpt_T_min   0.867
_shelx_estimated_absorpt_T_max   0.977

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_number            25886
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         1.185
_diffrn_reflns_theta_max         27.23
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             5217
_reflns_number_gt                4140
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

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

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#
_refine_special_details          
;loop_
  _platon_squeeze_void_nr
  _platon_squeeze_void_average_x
  _platon_squeeze_void_average_y
  _platon_squeeze_void_average_z
  _platon_squeeze_void_volume
  _platon_squeeze_void_count_electrons
  _platon_squeeze_void_content
   1  0.250  0.741  0.500        93        37 ' '
   2  0.250  0.247  1.000        93        37 ' '
   3  0.750  0.241  0.500        93        37 ' '
   4  0.750  0.747  1.000        93        37 ' '
_platon_squeeze_void_probe_radius                  1.20
_platon_squeeze_details                           ?

  The unit cell contains a mixture of disordered toluene and acetone molecules
  in the interstitial space of the structure and has been treated as a diffuse 
  contribution to the overall scattering without specific atoms positions by 
  PLATON/SQUEEZE. Due to the uncertainity of the number of each molecule in the
  unit cell, values of the squeezed electron density was not reported in the 
  CIF file.
  
  References:
  Spek, A.L. (2009). Acta Cryst. D65, 148-155.
  Spek, A.L. (2015). Acta Cryst. C71, 9-18.,SQUEEZE
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²+3.9575P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5217
_refine_ls_number_parameters     383
_refine_ls_number_restraints     124
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.049

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


#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
Cl1 Cl 0.59781(2) 1.27325(10) 0.25571(2) 0.02935(12) Uani 1 1 d . . . . .
Cl2 Cl 0.67791(2) 0.64063(11) 0.37368(2) 0.03081(12) Uani 1 1 d . . . . .
O1 O 0.54643(4) 1.0761(3) 0.45264(3) 0.0261(3) Uani 1 1 d . . . . .
H1A H 0.5594(4) 0.953(5) 0.4701(6) 0.039 Uiso 1 1 calc R U . . .
O2 O 0.61534(4) 1.0644(3) 0.42922(4) 0.0351(3) Uani 1 1 d . . . . .
N1 N 0.60938(5) 1.0558(3) 0.33946(4) 0.0238(3) Uani 1 1 d D . . . .
H1B H 0.6209(7) 1.062(5) 0.3636(5) 0.054(7) Uiso 1 1 d D . . . .
C1 C 0.63990(5) 0.9507(4) 0.31343(5) 0.0217(4) Uani 1 1 d . . . . .
C2 C 0.67511(6) 0.7628(4) 0.32580(5) 0.0234(4) Uani 1 1 d . . . . .
C3 C 0.70801(6) 0.6711(4) 0.30173(5) 0.0264(4) Uani 1 1 d . . . . .
H3 H 0.73157 0.545447 0.311316 0.032 Uiso 1 1 calc R U . . .
C4 C 0.70603(6) 0.7653(4) 0.26353(5) 0.0263(4) Uani 1 1 d . . . . .
H4 H 0.728163 0.702618 0.246644 0.032 Uiso 1 1 calc R U . . .
C5 C 0.67199(6) 0.9498(4) 0.24995(5) 0.0244(4) Uani 1 1 d . . . . .
H5 H 0.670764 1.015075 0.223772 0.029 Uiso 1 1 calc R U . . .
C6 C 0.63955(6) 1.0401(4) 0.27453(5) 0.0225(4) Uani 1 1 d . . . . .
C7 C 0.56222(5) 1.0008(4) 0.33625(5) 0.0195(3) Uani 1 1 d . . . . .
C8 C 0.53495(5) 1.1337(3) 0.36300(5) 0.0184(3) Uani 1 1 d . . . . .
C9 C 0.48873(6) 1.0707(4) 0.36110(5) 0.0239(4) Uani 1 1 d . . . . .
H9 H 0.470145 1.15634 0.379337 0.029 Uiso 1 1 calc R U . . .
C10 C 0.46919(6) 0.8860(4) 0.33324(5) 0.0274(4) Uani 1 1 d . . . . .
H10 H 0.437563 0.84545 0.332429 0.033 Uiso 1 1 calc R U . . .
C11 C 0.49601(6) 0.7614(4) 0.30671(5) 0.0282(4) Uani 1 1 d . . . . .
H11 H 0.482753 0.636022 0.287347 0.034 Uiso 1 1 calc R U . . .
C12 C 0.54214(6) 0.8182(4) 0.30815(5) 0.0244(4) Uani 1 1 d . . . . .
H12 H 0.560319 0.731289 0.289703 0.029 Uiso 1 1 calc R U . . .
C13 C 0.55571(6) 1.3309(4) 0.39434(5) 0.0215(4) Uani 1 1 d . . . . .
H13A H 0.579558 1.451331 0.383709 0.026 Uiso 1 1 calc R U . . .
H13B H 0.532077 1.458726 0.403858 0.026 Uiso 1 1 calc R U . . .
C14 C 0.57610(6) 1.1480(4) 0.42735(5) 0.0232(4) Uani 1 1 d . . . . .
N2A N 0.57536(13) 0.6889(8) 0.50374(11) 0.0242(6) Uani 0.878(4) 1 d . . P A 1
N3A N 0.61659(6) 0.0536(4) 0.58519(6) 0.0211(4) Uani 0.878(4) 1 d . . P A 1
N4A N 0.65525(6) -0.0481(4) 0.58158(5) 0.0217(4) Uani 0.878(4) 1 d . . P A 1
N5A N 0.70043(14) -0.6759(10) 0.66361(13) 0.0252(8) Uani 0.878(4) 1 d . . P A 1
C15A C 0.61656(10) 0.5729(7) 0.50280(8) 0.0257(5) Uani 0.878(4) 1 d . . P A 1
H15A H 0.635798 0.638451 0.483654 0.031 Uiso 0.878(4) 1 calc R U P A 1
C16A C 0.63265(9) 0.3619(6) 0.52835(8) 0.0242(5) Uani 0.878(4) 1 d . . P A 1
H16A H 0.662166 0.282833 0.52678 0.029 Uiso 0.878(4) 1 calc R U P A 1
C17A C 0.60446(9) 0.2689(5) 0.55634(6) 0.0200(5) Uani 0.878(4) 1 d . . P A 1
C18A C 0.56148(8) 0.3873(5) 0.55779(6) 0.0225(5) Uani 0.878(4) 1 d . . P A 1
H18A H 0.541553 0.326108 0.57666 0.027 Uiso 0.878(4) 1 calc R U P A 1
C19A C 0.54848(11) 0.5980(9) 0.53081(11) 0.0260(6) Uani 0.878(4) 1 d . . P A 1
H19A H 0.51915 0.68115 0.531649 0.031 Uiso 0.878(4) 1 calc R U P A 1
C20A C 0.66837(10) -0.2597(5) 0.61037(7) 0.0196(5) Uani 0.878(4) 1 d . . P A 1
C21A C 0.70898(10) -0.3980(6) 0.60575(8) 0.0239(6) Uani 0.878(4) 1 d . . P A 1
H21A H 0.726762 -0.353032 0.584614 0.029 Uiso 0.878(4) 1 calc R U P A 1
C22A C 0.72312(12) -0.6059(9) 0.63306(13) 0.0266(7) Uani 0.878(4) 1 d . . P A 1
H22A H 0.7508 -0.703729 0.629567 0.032 Uiso 0.878(4) 1 calc R U P A 1
C23A C 0.66126(12) -0.5373(8) 0.66729(10) 0.0240(7) Uani 0.878(4) 1 d . . P A 1
H23A H 0.644455 -0.584028 0.688972 0.029 Uiso 0.878(4) 1 calc R U P A 1
C24A C 0.64349(10) -0.3305(6) 0.64167(8) 0.0232(6) Uani 0.878(4) 1 d . . P A 1
H24 H 0.615236 -0.2403 0.645431 0.028 Uiso 0.878(4) 1 calc R U P A 1
N3B N 0.6469(5) 0.059(3) 0.5691(4) 0.0211(4) Uani 0.122(4) 1 d . U P A 2
N4B N 0.6262(5) -0.032(3) 0.5981(4) 0.0217(4) Uani 0.122(4) 1 d . U P A 2
N2B N 0.5785(8) 0.703(6) 0.5024(8) 0.026(3) Uani 0.122(4) 1 d G U P A 2
C15B C 0.6212(8) 0.606(5) 0.4938(6) 0.0257(5) Uani 0.122(4) 1 d G U P A 2
H15B H 0.635838 0.687146 0.472707 0.031 Uiso 0.122(4) 1 calc R U P A 2
C16B C 0.6426(5) 0.390(4) 0.5161(5) 0.024(2) Uani 0.122(4) 1 d G U P A 2
H16B H 0.67178 0.323559 0.510244 0.028 Uiso 0.122(4) 1 calc R U P A 2
C17B C 0.6212(5) 0.271(3) 0.5470(4) 0.020(2) Uani 0.122(4) 1 d G U P A 2
C18B C 0.5785(6) 0.368(4) 0.5557(5) 0.0225(5) Uani 0.122(4) 1 d G U P A 2
H18B H 0.56387 0.286727 0.576784 0.027 Uiso 0.122(4) 1 calc R U P A 2
C19B C 0.5571(6) 0.584(6) 0.5334(8) 0.024(3) Uani 0.122(4) 1 d G U P A 2
H19B H 0.527927 0.650315 0.539248 0.028 Uiso 0.122(4) 1 calc R U P A 2
C20B C 0.6533(5) -0.249(3) 0.6201(4) 0.014(2) Uani 0.122(4) 1 d G U P A 2
C21B C 0.6963(6) -0.344(4) 0.6117(5) 0.016(3) Uani 0.122(4) 1 d G U P A 2
H21B H 0.710721 -0.262858 0.590405 0.019 Uiso 0.122(4) 1 calc R U P A 2
C22B C 0.7180(6) -0.556(5) 0.6343(8) 0.018(4) Uani 0.122(4) 1 d G U P A 2
H22B H 0.747345 -0.620905 0.628504 0.021 Uiso 0.122(4) 1 calc R U P A 2
N5B N 0.6969(8) -0.674(6) 0.6654(8) 0.015(4) Uani 0.122(4) 1 d G U P A 2
C23B C 0.6539(7) -0.580(5) 0.6738(6) 0.014(3) Uani 0.122(4) 1 d G U P A 2
H23B H 0.639478 -0.660408 0.695067 0.017 Uiso 0.122(4) 1 calc R U P A 2
C24B C 0.6322(5) -0.367(4) 0.6512(5) 0.018(3) Uani 0.122(4) 1 d G U P A 2
H24B H 0.602853 -0.30236 0.656969 0.021 Uiso 0.122(4) 1 calc R 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
Cl1 C6 1.7335(18) . ?
Cl2 C2 1.7410(19) . ?
O1 C14 1.320(2) . ?
O1 H1A 0.90(2) . ?
O2 C14 1.218(2) . ?
N1 C1 1.402(2) . ?
N1 C7 1.411(2) . ?
N1 H1B 0.878(16) . ?
C1 C2 1.402(2) . ?
C1 C6 1.402(2) . ?
C2 C3 1.387(2) . ?
C3 C4 1.384(3) . ?
C3 H3 0.95 . ?
C4 C5 1.379(3) . ?
C4 H4 0.95 . ?
C5 C6 1.387(2) . ?
C5 H5 0.95 . ?
C7 C12 1.390(2) . ?
C7 C8 1.408(2) . ?
C8 C9 1.391(2) . ?
C8 C13 1.514(2) . ?
C9 C10 1.384(3) . ?
C9 H9 0.95 . ?
C10 C11 1.378(3) . ?
C10 H10 0.95 . ?
C11 C12 1.383(2) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
C13 C14 1.512(2) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
N2A C15A 1.332(3) . ?
N2A C19A 1.334(3) . ?
N3A N4A 1.249(3) . ?
N3A C17A 1.440(3) . ?
N4A C20A 1.432(3) . ?
N5A C22A 1.327(3) . ?
N5A C23A 1.337(3) . ?
C15A C16A 1.382(3) . ?
C15A H15A 0.95 . ?
C16A C17A 1.386(3) . ?
C16A H16A 0.95 . ?
C17A C18A 1.386(3) . ?
C18A C19A 1.387(3) . ?
C18A H18A 0.95 . ?
C19A H19A 0.95 . ?
C20A C21A 1.379(3) . ?
C20A C24A 1.386(3) . ?
C21A C22A 1.394(3) . ?
C21A H21A 0.95 . ?
C22A H22A 0.95 . ?
C23A C24A 1.385(3) . ?
C23A H23A 0.95 . ?
C24A H24 0.95 . ?
N3B N4B 1.28(2) . ?
N3B C17B 1.43(2) . ?
N4B C20B 1.47(2) . ?
N2B C15B 1.39 . ?
N2B C19B 1.39 . ?
C15B C16B 1.39 . ?
C15B H15B 0.95 . ?
C16B C17B 1.39 . ?
C16B H16B 0.95 . ?
C17B C18B 1.39 . ?
C18B C19B 1.39 . ?
C18B H18B 0.95 . ?
C19B H19B 0.95 . ?
C20B C21B 1.39 . ?
C20B C24B 1.39 . ?
C21B C22B 1.39 . ?
C21B H21B 0.95 . ?
C22B N5B 1.39 . ?
C22B H22B 0.95 . ?
N5B C23B 1.39 . ?
C23B C24B 1.39 . ?
C23B H23B 0.95 . ?
C24B H24B 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O1 H1A 109.5 . . ?
C1 N1 C7 124.01(14) . . ?
C1 N1 H1B 113.3(16) . . ?
C7 N1 H1B 113.3(15) . . ?
C2 C1 C6 115.59(15) . . ?
C2 C1 N1 121.25(16) . . ?
C6 C1 N1 123.01(16) . . ?
C3 C2 C1 123.02(17) . . ?
C3 C2 Cl2 118.47(14) . . ?
C1 C2 Cl2 118.51(13) . . ?
C4 C3 C2 119.06(17) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 120.10(16) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.96(17) . . ?
C4 C5 H5 120 . . ?
C6 C5 H5 120 . . ?
C5 C6 C1 122.26(16) . . ?
C5 C6 Cl1 117.65(14) . . ?
C1 C6 Cl1 120.08(13) . . ?
C12 C7 C8 119.34(15) . . ?
C12 C7 N1 122.38(15) . . ?
C8 C7 N1 118.28(15) . . ?
C9 C8 C7 118.61(15) . . ?
C9 C8 C13 120.50(15) . . ?
C7 C8 C13 120.84(15) . . ?
C10 C9 C8 121.51(16) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C11 C10 C9 119.44(16) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 120.27(17) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 120.80(16) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C14 C13 C8 108.27(14) . . ?
C14 C13 H13A 110 . . ?
C8 C13 H13A 110 . . ?
C14 C13 H13B 110 . . ?
C8 C13 H13B 110 . . ?
H13A C13 H13B 108.4 . . ?
O2 C14 O1 123.69(16) . . ?
O2 C14 C13 123.12(16) . . ?
O1 C14 C13 113.09(15) . . ?
C15A N2A C19A 118.4(2) . . ?
N4A N3A C17A 112.4(2) . . ?
N3A N4A C20A 113.4(2) . . ?
C22A N5A C23A 116.3(2) . . ?
N2A C15A C16A 123.1(2) . . ?
N2A C15A H15A 118.4 . . ?
C16A C15A H15A 118.4 . . ?
C15A C16A C17A 118.0(2) . . ?
C15A C16A H16A 121 . . ?
C17A C16A H16A 121 . . ?
C16A C17A C18A 119.67(19) . . ?
C16A C17A N3A 124.5(2) . . ?
C18A C17A N3A 115.9(2) . . ?
C17A C18A C19A 117.9(2) . . ?
C17A C18A H18A 121 . . ?
C19A C18A H18A 121 . . ?
N2A C19A C18A 122.9(2) . . ?
N2A C19A H19A 118.6 . . ?
C18A C19A H19A 118.6 . . ?
C21A C20A C24A 119.32(19) . . ?
C21A C20A N4A 115.9(2) . . ?
C24A C20A N4A 124.8(2) . . ?
C20A C21A C22A 117.9(2) . . ?
C20A C21A H21A 121 . . ?
C22A C21A H21A 121 . . ?
N5A C22A C21A 124.2(2) . . ?
N5A C22A H22A 117.9 . . ?
C21A C22A H22A 117.9 . . ?
N5A C23A C24A 124.5(2) . . ?
N5A C23A H23A 117.7 . . ?
C24A C23A H23A 117.7 . . ?
C23A C24A C20A 117.7(2) . . ?
C23A C24A H24 121.2 . . ?
C20A C24A H24 121.2 . . ?
N4B N3B C17B 112.4(16) . . ?
N3B N4B C20B 111.0(16) . . ?
C15B N2B C19B 120 . . ?
C16B C15B N2B 120 . . ?
C16B C15B H15B 120 . . ?
N2B C15B H15B 120 . . ?
C15B C16B C17B 120 . . ?
C15B C16B H16B 120 . . ?
C17B C16B H16B 120 . . ?
C18B C17B C16B 120 . . ?
C18B C17B N3B 124.4(13) . . ?
C16B C17B N3B 115.5(13) . . ?
C19B C18B C17B 120 . . ?
C19B C18B H18B 120 . . ?
C17B C18B H18B 120 . . ?
C18B C19B N2B 120 . . ?
C18B C19B H19B 120 . . ?
N2B C19B H19B 120 . . ?
C21B C20B C24B 120 . . ?
C21B C20B N4B 125.6(12) . . ?
C24B C20B N4B 114.4(12) . . ?
C20B C21B C22B 120 . . ?
C20B C21B H21B 120 . . ?
C22B C21B H21B 120 . . ?
C21B C22B N5B 120 . . ?
C21B C22B H22B 120 . . ?
N5B C22B H22B 120 . . ?
C23B N5B C22B 120 . . ?
N5B C23B C24B 120 . . ?
N5B C23B H23B 120 . . ?
C24B C23B H23B 120 . . ?
C23B C24B C20B 120 . . ?
C23B C24B H24B 120 . . ?
C20B C24B H24B 120 . . ?

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
O1 H1A N2A 0.9 1.73 2.622(3) 170.4 .
O1 H1A N2B 0.9 1.68 2.576(13) 174.1 .
N1 H1B O2 0.878(16) 2.276(18) 3.084(2) 153(2) .


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_diclofenac4-4'-APxy
_database_code_depnum_ccdc_archive 'CCDC 1913840'
_audit_update_record             
;
2019-05-03 deposited with the CCDC.	2019-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT911_diclofenac4-4'-APxy 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
RESPONSE: These reflections were omitted due to low observed versus calculated
          values.
;
# end Validation Reply Form

_audit_creation_date             2019-04-30T10:17:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C24 H19 Cl2 N5 O2'
_chemical_formula_weight         480.34

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   29.5915(4)
_cell_length_b                   4.67650(10)
_cell_length_c                   34.4083(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.1420(10)
_cell_angle_gamma                90
_cell_volume                     4749.14(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13028
_cell_measurement_theta_min      3.793
_cell_measurement_theta_max      77.078

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

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear orange'
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.037
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             1984

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

_exptl_absorpt_coefficient_mu    2.716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.71375
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.606
_shelx_estimated_absorpt_T_max   0.906

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

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      100(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                 'CCD plate'
_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      -0.0146341
_diffrn_orient_matrix_ub_12      -0.3099151
_diffrn_orient_matrix_ub_13      0.0075978
_diffrn_orient_matrix_ub_21      -0.0104565
_diffrn_orient_matrix_ub_22      -0.0448212
_diffrn_orient_matrix_ub_23      -0.0440875
_diffrn_orient_matrix_ub_31      0.049002
_diffrn_orient_matrix_ub_32      -0.1023079
_diffrn_orient_matrix_ub_33      -0.003683
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_number            26656
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         3.807
_diffrn_reflns_theta_max         77.533
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_reflns_Friedel_coverage         0
_reflns_number_total             4943
_reflns_number_gt                4500
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (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   mixed

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


_refine_special_details          
;
 The structure also contained positional disorder about the 4,4'-
 azopyridine molecule which resulted in split sites (A and B). The
 SOF value for the A and B sites were 0.92 and 0.08, respectively.
 The use of EADP contraints and SIMU, DELU, and free variable DFIX restraints 
 were required to maintain reasonable ADP for the minor components. The 
 inconsistent reflections 2 2 37 and 4 2 38 were also omitted.
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.250 0.410 0.500 109 36 ' '
2 0.250 0.460 1.000 109 36 ' '
3 0.750 0.033 0.500 109 36 ' '
4 0.750 0.084 1.000 109 36 ' '
# Missing Reflections Below sin(th)/lambda = 0.25
loop_
_platon_missing_refln_index_h
_platon_missing_refln_index_k
_platon_missing_refln_index_l
_platon_missing_refln_theta
4 0 0 5.965
-2 0 2 3.772
0 0 2 2.542
2 0 2 4.057
-2 0 4 5.708
0 0 4 5.090
-4 0 6 9.364
-2 0 6 8.004
0 0 6 7.647
-4 0 8 11.473
-2 0 8 10.438
0 0 8 10.220
-6 0 10 15.161
-4 0 10 13.763
-2 0 10 12.946
0 0 10 12.814
-6 0 12 17.360
-4 0 12 16.171
-6 0 14 19.696
-2 0 14 18.121
-4 0 16 21.245
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?
_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)+(0.0838P)²+11.2270P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4943
_refine_ls_number_parameters     360
_refine_ls_number_restraints     480
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1496
_refine_ls_wR_factor_gt          0.1447
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.927
_refine_diff_density_min         -0.984
_refine_diff_density_rms         0.075

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


#----------------------------------------------------------------------------#
#                   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'
Cl Cl 0.3639 0.7018 '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
Cl1 Cl 0.32221(2) 0.63176(13) 0.62582(2) 0.02976(17) Uani 1 1 d . . . . .
Cl2 Cl 0.40190(2) 1.26819(12) 0.74371(2) 0.02859(16) Uani 1 1 d . . . . .
O1 O 0.45392(5) 1.0710(4) 0.54721(5) 0.0271(4) Uani 1 1 d . . . . .
H1 H 0.44207 0.954624 0.530898 0.041 Uiso 1 1 calc R U . . .
O2 O 0.38540(6) 1.0517(4) 0.57084(5) 0.0349(4) Uani 1 1 d . . . . .
N1 N 0.39060(6) 1.0463(4) 0.66001(6) 0.0243(4) Uani 1 1 d . . . . .
H1A H 0.3789(12) 1.050(8) 0.6356(12) 0.053(10) Uiso 1 1 d . . . . .
N3A N 0.38421(7) 0.0508(5) 0.41448(6) 0.0213(4) Uani 0.915(4) 1 d D . P A 1
N4A N 0.34542(7) -0.0520(5) 0.41763(6) 0.0215(5) Uani 0.915(4) 1 d D . P A 1
N2A N 0.42556(7) 0.6880(4) 0.49572(5) 0.0230(5) Uani 0.915(4) 1 d G . P A 1
C15A C 0.45373(6) 0.5968(5) 0.46755(6) 0.0277(6) Uani 0.915(4) 1 d G . P A 1
H15A H 0.482871 0.679916 0.466232 0.033 Uiso 0.915(4) 1 calc R U P A 1
C16A C 0.43925(7) 0.3841(5) 0.44132(5) 0.0240(5) Uani 0.915(4) 1 d G . P A 1
H16A H 0.458494 0.321833 0.422067 0.029 Uiso 0.915(4) 1 calc R U P A 1
C17A C 0.39660(7) 0.2626(3) 0.44325(5) 0.0206(5) Uani 0.915(4) 1 d DG . P A 1
C18A C 0.36844(5) 0.3537(4) 0.47141(6) 0.0248(6) Uani 0.915(4) 1 d G . P A 1
H18A H 0.339291 0.270632 0.472728 0.03 Uiso 0.915(4) 1 calc R U P A 1
C19A C 0.38292(6) 0.5664(4) 0.49764(6) 0.0251(6) Uani 0.915(4) 1 d G . P A 1
H19A H 0.363667 0.628716 0.516894 0.03 Uiso 0.915(4) 1 calc R U P A 1
C20A C 0.33286(9) -0.2645(6) 0.38845(8) 0.0245(6) Uani 0.915(4) 1 d DG . P A 1
C21A C 0.29172(7) -0.3996(5) 0.39295(6) 0.0241(6) Uani 0.915(4) 1 d G . P A 1
H21A H 0.274517 -0.351142 0.414269 0.029 Uiso 0.915(4) 1 calc R U P A 1
C22A C 0.27574(5) -0.6055(4) 0.36625(6) 0.0239(6) Uani 0.915(4) 1 d G . P A 1
H22A H 0.247623 -0.697806 0.369322 0.029 Uiso 0.915(4) 1 calc R U P A 1
N5A N 0.30090(6) -0.6764(3) 0.33505(5) 0.0194(4) Uani 0.915(4) 1 d G . P A 1
C23A C 0.34204(7) -0.5413(6) 0.33055(7) 0.0259(6) Uani 0.915(4) 1 d G . P A 1
H23A H 0.359243 -0.589761 0.309231 0.031 Uiso 0.915(4) 1 calc R U P A 1
C24A C 0.35802(8) -0.3354(7) 0.35725(9) 0.0282(6) Uani 0.915(4) 1 d G . P A 1
H24A H 0.386137 -0.243095 0.354178 0.034 Uiso 0.915(4) 1 calc R U P A 1
N3B N 0.3539(7) 0.041(5) 0.4307(6) 0.0213(4) Uani 0.085(4) 1 d D U P A 2
N4B N 0.3753(7) -0.034(5) 0.4033(6) 0.0215(5) Uani 0.085(4) 1 d D U P A 2
N2B N 0.4238(9) 0.659(5) 0.5034(6) 0.0230(5) Uani 0.085(4) 1 d G U P A 2
C15B C 0.4447(7) 0.578(6) 0.4702(7) 0.0162(17) Uani 0.085(4) 1 d G U P A 2
H15B H 0.473416 0.655401 0.465288 0.019 Uiso 0.085(4) 1 calc R U P A 2
C16B C 0.4236(8) 0.384(5) 0.4443(6) 0.019(2) Uani 0.085(4) 1 d G U P A 2
H16B H 0.437852 0.328408 0.421616 0.023 Uiso 0.085(4) 1 calc R U P A 2
C17B C 0.3815(8) 0.271(4) 0.4515(6) 0.0196(17) Uani 0.085(4) 1 d DG U P A 2
C18B C 0.3607(6) 0.352(5) 0.4847(6) 0.020(2) Uani 0.085(4) 1 d G U P A 2
H18B H 0.331933 0.275034 0.489653 0.024 Uiso 0.085(4) 1 calc R U P A 2
C19B C 0.3818(8) 0.546(5) 0.5107(6) 0.0215(18) Uani 0.085(4) 1 d G U P A 2
H19B H 0.367496 0.602028 0.533326 0.026 Uiso 0.085(4) 1 calc R U P A 2
C20B C 0.3370(10) -0.220(7) 0.3894(9) 0.0213(15) Uani 0.085(4) 1 d DG U P A 2
C21B C 0.2960(8) -0.320(6) 0.4014(6) 0.0228(19) Uani 0.085(4) 1 d G U P A 2
H21B H 0.283956 -0.241105 0.423928 0.027 Uiso 0.085(4) 1 calc R U P A 2
C22B C 0.2728(6) -0.535(5) 0.3806(6) 0.0221(17) Uani 0.085(4) 1 d G U P A 2
H22B H 0.244771 -0.603563 0.388808 0.027 Uiso 0.085(4) 1 calc R U P A 2
N5B N 0.2905(7) -0.651(4) 0.3477(6) 0.0194(4) Uani 0.085(4) 1 d G U P A 2
C23B C 0.3314(8) -0.551(6) 0.3357(7) 0.0136(17) Uani 0.085(4) 1 d G U P A 2
H23B H 0.343526 -0.629627 0.313171 0.016 Uiso 0.085(4) 1 calc R U P A 2
C24B C 0.3547(9) -0.335(8) 0.3565(10) 0.0189(19) Uani 0.085(4) 1 d G U P A 2
H24B H 0.382712 -0.267169 0.348291 0.023 Uiso 0.085(4) 1 calc R U P A 2
C1 C 0.32501(7) 0.7566(5) 0.67361(7) 0.0228(4) Uani 1 1 d . . . . .
C2 C 0.36009(7) 0.9433(5) 0.68614(6) 0.0213(4) Uani 1 1 d . . . . .
C3 C 0.36047(7) 1.0345(5) 0.72488(6) 0.0228(4) Uani 1 1 d . . . . .
C4 C 0.32784(7) 0.9466(5) 0.74952(7) 0.0238(4) Uani 1 1 d . . . . .
H4 H 0.328906 1.01343 0.775644 0.029 Uiso 1 1 calc R U . . .
C5 C 0.29390(8) 0.7620(5) 0.73582(7) 0.0255(5) Uani 1 1 d . . . . .
H5 H 0.271759 0.70063 0.752672 0.031 Uiso 1 1 calc R U . . .
C6 C 0.29196(7) 0.6657(5) 0.69765(7) 0.0253(5) Uani 1 1 d . . . . .
H6 H 0.268503 0.540134 0.688058 0.03 Uiso 1 1 calc R U . . .
C7 C 0.43777(7) 0.9954(5) 0.66361(6) 0.0204(4) Uani 1 1 d . . . . .
C8 C 0.46501(7) 1.1303(4) 0.63711(6) 0.0200(4) Uani 1 1 d . . . . .
C9 C 0.51122(7) 1.0714(5) 0.63947(6) 0.0245(5) Uani 1 1 d . . . . .
H9 H 0.529764 1.158796 0.62143 0.029 Uiso 1 1 calc R U . . .
C10 C 0.53082(8) 0.8884(5) 0.66748(7) 0.0288(5) Uani 1 1 d . . . . .
H10 H 0.56244 0.851049 0.668585 0.035 Uiso 1 1 calc R U . . .
C11 C 0.50397(8) 0.7600(5) 0.69393(7) 0.0287(5) Uani 1 1 d . . . . .
H11 H 0.517235 0.635142 0.713334 0.034 Uiso 1 1 calc R U . . .
C12 C 0.45774(8) 0.8138(5) 0.69206(7) 0.0255(5) Uani 1 1 d . . . . .
H12 H 0.43953 0.726165 0.710331 0.031 Uiso 1 1 calc R U . . .
C13 C 0.44418(7) 1.3250(5) 0.60557(6) 0.0222(4) Uani 1 1 d . . . . .
H13A H 0.467591 1.453346 0.596055 0.027 Uiso 1 1 calc R U . . .
H13B H 0.420196 1.444106 0.61602 0.027 Uiso 1 1 calc R U . . .
C14 C 0.42425(8) 1.1395(5) 0.57261(6) 0.0241(4) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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
Cl1 C1 1.741(2) . ?
Cl2 C3 1.733(2) . ?
O1 C14 1.322(3) . ?
O1 H1 0.84 . ?
O2 C14 1.218(3) . ?
N1 C2 1.405(3) . ?
N1 C7 1.413(3) . ?
N1 H1A 0.88(4) . ?
N3A N4A 1.256(3) . ?
N3A C17A 1.429(3) . ?
N4A C20A 1.442(3) . ?
N2A C15A 1.39 . ?
N2A C19A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.95 . ?
C16A C17A 1.39 . ?
C16A H16A 0.95 . ?
C17A C18A 1.39 . ?
C18A C19A 1.39 . ?
C18A H18A 0.95 . ?
C19A H19A 0.95 . ?
C20A C21A 1.39 . ?
C20A C24A 1.39 . ?
C21A C22A 1.39 . ?
C21A H21A 0.95 . ?
C22A N5A 1.39 . ?
C22A H22A 0.95 . ?
N5A C23A 1.39 . ?
C23A C24A 1.39 . ?
C23A H23A 0.95 . ?
C24A H24A 0.95 . ?
N3B N4B 1.23(2) . ?
N3B C17B 1.50(2) . ?
N3B C20B 1.91(3) . ?
N4B C20B 1.48(2) . ?
N2B C15B 1.39 . ?
N2B C19B 1.39 . ?
C15B C16B 1.39 . ?
C15B H15B 0.95 . ?
C16B C17B 1.39 . ?
C16B H16B 0.95 . ?
C17B C18B 1.39 . ?
C18B C19B 1.39 . ?
C18B H18B 0.95 . ?
C19B H19B 0.95 . ?
C20B C21B 1.39 . ?
C20B C24B 1.39 . ?
C21B C22B 1.39 . ?
C21B H21B 0.95 . ?
C22B N5B 1.39 . ?
C22B H22B 0.95 . ?
N5B C23B 1.39 . ?
C23B C24B 1.39 . ?
C23B H23B 0.95 . ?
C24B H24B 0.95 . ?
C1 C6 1.392(3) . ?
C1 C2 1.400(3) . ?
C2 C3 1.399(3) . ?
C3 C4 1.392(3) . ?
C4 C5 1.381(3) . ?
C4 H4 0.95 . ?
C5 C6 1.386(3) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C12 1.395(3) . ?
C7 C8 1.409(3) . ?
C8 C9 1.392(3) . ?
C8 C13 1.513(3) . ?
C9 C10 1.384(3) . ?
C9 H9 0.95 . ?
C10 C11 1.387(3) . ?
C10 H10 0.95 . ?
C11 C12 1.388(3) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
C13 C14 1.514(3) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?

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
C14 O1 H1 109.5 . . ?
C2 N1 C7 124.25(18) . . ?
C2 N1 H1A 113(2) . . ?
C7 N1 H1A 114(2) . . ?
N4A N3A C17A 113.3(2) . . ?
N3A N4A C20A 113.2(2) . . ?
C15A N2A C19A 120 . . ?
N2A C15A C16A 120 . . ?
N2A C15A H15A 120 . . ?
C16A C15A H15A 120 . . ?
C15A C16A C17A 120 . . ?
C15A C16A H16A 120 . . ?
C17A C16A H16A 120 . . ?
C18A C17A C16A 120 . . ?
C18A C17A N3A 123.95(16) . . ?
C16A C17A N3A 116.03(16) . . ?
C19A C18A C17A 120 . . ?
C19A C18A H18A 120 . . ?
C17A C18A H18A 120 . . ?
C18A C19A N2A 120 . . ?
C18A C19A H19A 120 . . ?
N2A C19A H19A 120 . . ?
C21A C20A C24A 120 . . ?
C21A C20A N4A 114.80(17) . . ?
C24A C20A N4A 125.19(17) . . ?
C22A C21A C20A 120 . . ?
C22A C21A H21A 120 . . ?
C20A C21A H21A 120 . . ?
C21A C22A N5A 120 . . ?
C21A C22A H22A 120 . . ?
N5A C22A H22A 120 . . ?
C23A N5A C22A 120 . . ?
N5A C23A C24A 120 . . ?
N5A C23A H23A 120 . . ?
C24A C23A H23A 120 . . ?
C23A C24A C20A 120 . . ?
C23A C24A H24A 120 . . ?
C20A C24A H24A 120 . . ?
N4B N3B C17B 106(2) . . ?
N4B N3B C20B 50.7(14) . . ?
C17B N3B C20B 156.3(17) . . ?
N3B N4B C20B 90(2) . . ?
C15B N2B C19B 120 . . ?
C16B C15B N2B 120 . . ?
C16B C15B H15B 120 . . ?
N2B C15B H15B 120 . . ?
C17B C16B C15B 120 . . ?
C17B C16B H16B 120 . . ?
C15B C16B H16B 120 . . ?
C16B C17B C18B 120 . . ?
C16B C17B N3B 130.6(17) . . ?
C18B C17B N3B 109.1(16) . . ?
C17B C18B C19B 120 . . ?
C17B C18B H18B 120 . . ?
C19B C18B H18B 120 . . ?
C18B C19B N2B 120 . . ?
C18B C19B H19B 120 . . ?
N2B C19B H19B 120 . . ?
C21B C20B C24B 120 . . ?
C21B C20B N4B 139.9(19) . . ?
C24B C20B N4B 99.6(19) . . ?
C21B C20B N3B 100.3(15) . . ?
C24B C20B N3B 139.4(15) . . ?
N4B C20B N3B 39.8(10) . . ?
C20B C21B C22B 120 . . ?
C20B C21B H21B 120 . . ?
C22B C21B H21B 120 . . ?
N5B C22B C21B 120 . . ?
N5B C22B H22B 120 . . ?
C21B C22B H22B 120 . . ?
C22B N5B C23B 120 . . ?
N5B C23B C24B 120 . . ?
N5B C23B H23B 120 . . ?
C24B C23B H23B 120 . . ?
C23B C24B C20B 120 . . ?
C23B C24B H24B 120 . . ?
C20B C24B H24B 120 . . ?
C6 C1 C2 123.0(2) . . ?
C6 C1 Cl1 118.11(18) . . ?
C2 C1 Cl1 118.90(16) . . ?
C3 C2 C1 115.98(19) . . ?
C3 C2 N1 123.0(2) . . ?
C1 C2 N1 120.9(2) . . ?
C4 C3 C2 122.2(2) . . ?
C4 C3 Cl2 117.49(18) . . ?
C2 C3 Cl2 120.35(16) . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
C12 C7 C8 119.6(2) . . ?
C12 C7 N1 122.02(19) . . ?
C8 C7 N1 118.40(19) . . ?
C9 C8 C7 118.7(2) . . ?
C9 C8 C13 120.56(19) . . ?
C7 C8 C13 120.74(19) . . ?
C10 C9 C8 121.5(2) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 119.6(2) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120 . . ?
C12 C11 H11 120 . . ?
C11 C12 C7 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
C8 C13 C14 108.00(18) . . ?
C8 C13 H13A 110.1 . . ?
C14 C13 H13A 110.1 . . ?
C8 C13 H13B 110.1 . . ?
C14 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
O2 C14 O1 123.7(2) . . ?
O2 C14 C13 123.1(2) . . ?
O1 C14 C13 113.12(19) . . ?

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 N2A^a 0.84 1.78 2.615(2) 171.2 . yes
O1 H1 N2B^b 0.84 1.74 2.564(16) 167.7 . yes
N1 H1A O2 0.88(4) 2.25(4) 3.061(3) 152(3) . yes



# END of CIF
####################################################################### 
# 
# 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_diclofenac4-4'-APrt
_database_code_depnum_ccdc_archive 'CCDC 1913839'
_audit_update_record             
;
2019-05-03 deposited with the CCDC.	2019-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT250_diclofenacAPrt      
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.1 Note  
RESPONSE: Due to the disorder about the 4,4'-azopyridine.
;
_vrf_PLAT411_diclofenac4-4'-APrt 
;
PROBLEM: Short Inter H...H Contact  H4       ..H23B     .       2.06 Ang.  
RESPONSE: Due to the disorder about the 4,4'-azopyridine.
;
_vrf_PLAT911_diclofenac4-4'-APrt 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         70 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2019-04-29T15:13:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C24 H19 Cl2 N5 O2'
_chemical_formula_weight         480.34

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   29.7548(10)
_cell_length_b                   4.76130(10)
_cell_length_c                   34.8524(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.220(4)
_cell_angle_gamma                90
_cell_volume                     4924.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    12189
_cell_measurement_theta_min      2.954
_cell_measurement_theta_max      77.176

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

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear orange'
_exptl_crystal_size_max          0.375
_exptl_crystal_size_mid          0.032
_exptl_crystal_size_min          0.017
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             1984
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 1 0.0135
-8 -2 16 0.1138
-1 0 1 0.0095
1 0 -1 0.019
-1 1 1 0.1706
1 -1 -1 0.1957
-1 0 -1 0.003


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

_exptl_absorpt_coefficient_mu    2.619
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.48a (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  0.038
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.44
_shelx_estimated_absorpt_T_max   0.957

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

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      297(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                 'CCD plate'
_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      -0.0387875
_diffrn_orient_matrix_ub_12      -0.1120986
_diffrn_orient_matrix_ub_13      0.0226357
_diffrn_orient_matrix_ub_21      -0.0226219
_diffrn_orient_matrix_ub_22      -0.1256914
_diffrn_orient_matrix_ub_23      -0.0373296
_diffrn_orient_matrix_ub_31      0.0260835
_diffrn_orient_matrix_ub_32      -0.2762509
_diffrn_orient_matrix_ub_33      0.0077957
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_number            24081
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.978
_diffrn_reflns_theta_max         77.22
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.963
_reflns_Friedel_coverage         0
_reflns_number_total             4986
_reflns_number_gt                4029
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.48a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.48a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.48a (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   mixed

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

_refine_special_details          
;
 The structure also contained positional disorder about the 4,4'-
 azopyridine molecule which consisted of split sites (A and B). The
 SOF value for the A and B sites were 0.80 and 0.20, respectively.
 The use of SIMU, DELU, and free variable DFIX restraints were
 required to maintain reasonable ADP for the disordered components.
;
#loop_
#  _platon_squeeze_void_nr
#  _platon_squeeze_void_average_x
#  _platon_squeeze_void_average_y
#  _platon_squeeze_void_average_z
#  _platon_squeeze_void_volume
#  _platon_squeeze_void_count_electrons
#  _platon_squeeze_void_content
#   1  0.250  0.410  0.500       109        36 ' '
#   2  0.250  0.460  1.000       109        36 ' '
#   3  0.750  0.033  0.500       109        36 ' '
#   4  0.750  0.084  1.000       109        36 ' '
# Missing Reflections Below sin(th)/lambda = 0.25
loop_
_platon_missing_refln_index_h
_platon_missing_refln_index_k
_platon_missing_refln_index_l
_platon_missing_refln_theta
4 0 0 5.965
-2 0 2 3.772
0 0 2 2.542
2 0 2 4.057
-2 0 4 5.708
0 0 4 5.090
-4 0 6 9.364
-2 0 6 8.004
0 0 6 7.647
-4 0 8 11.473
-2 0 8 10.438
0 0 8 10.220
-6 0 10 15.161
-4 0 10 13.763
-2 0 10 12.946
0 0 10 12.814
-6 0 12 17.360
-4 0 12 16.171
-6 0 14 19.696
-2 0 14 18.121
-4 0 16 21.245
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?
_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)+(0.0994P)²+2.0998P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4986
_refine_ls_number_parameters     382
_refine_ls_number_restraints     301
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1695
_refine_ls_wR_factor_gt          0.159
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.048

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


#----------------------------------------------------------------------------#
#                   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'
Cl Cl 0.3639 0.7018 '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
Cl1 Cl 0.32228(2) 0.59678(18) 0.62610(2) 0.0792(2) Uani 1 1 d . . . . .
Cl2 Cl 0.40126(2) 1.22264(14) 0.74229(2) 0.0760(2) Uani 1 1 d . . . . .
O1 O 0.45516(6) 1.0491(4) 0.54889(5) 0.0698(5) Uani 1 1 d . . . . .
H1 H 0.44295 0.959428 0.530926 0.105 Uiso 1 1 calc R U . . .
O2 O 0.38733(6) 1.0217(5) 0.57120(5) 0.0858(6) Uani 1 1 d . . . . .
N1 N 0.39071(6) 1.0012(5) 0.65999(6) 0.0591(5) Uani 1 1 d . . . . .
H1A H 0.3786(9) 1.015(6) 0.6373(9) 0.071 Uiso 1 1 d . U . . .
N3A N 0.38536(10) 0.0701(6) 0.41443(8) 0.0512(7) Uani 0.803(8) 1 d D U P A 1
N4A N 0.34635(10) -0.0392(7) 0.41739(8) 0.0523(7) Uani 0.803(8) 1 d D U P A 1
N2A N 0.42764(14) 0.6881(8) 0.49491(9) 0.0565(9) Uani 0.803(8) 1 d G U P A 1
C15A C 0.45517(12) 0.6019(9) 0.46660(12) 0.0707(13) Uani 0.803(8) 1 d G U P A 1
H15A H 0.483397 0.68323 0.46505 0.085 Uiso 0.803(8) 1 calc R U P A 1
C16A C 0.44051(12) 0.3941(9) 0.44059(11) 0.0599(10) Uani 0.803(8) 1 d G U P A 1
H16A H 0.458925 0.336457 0.421649 0.072 Uiso 0.803(8) 1 calc R U P A 1
C17A C 0.39832(11) 0.2726(7) 0.44290(9) 0.0482(8) Uani 0.803(8) 1 d DG U P A 1
C18A C 0.37079(10) 0.3588(7) 0.47122(10) 0.0596(9) Uani 0.803(8) 1 d G U P A 1
H18A H 0.342565 0.277505 0.472761 0.072 Uiso 0.803(8) 1 calc R U P A 1
C19A C 0.38545(13) 0.5666(8) 0.49722(9) 0.0593(10) Uani 0.803(8) 1 d G U P A 1
H19A H 0.367037 0.624279 0.516163 0.071 Uiso 0.803(8) 1 calc R U P A 1
C20A C 0.33304(11) -0.2391(6) 0.38899(8) 0.0501(7) Uani 0.803(8) 1 d DG U P A 1
C21A C 0.29299(10) -0.3820(8) 0.39330(8) 0.0588(9) Uani 0.803(8) 1 d G U P A 1
H21A H 0.27646 -0.345 0.414359 0.071 Uiso 0.803(8) 1 calc R U P A 1
C22A C 0.27765(10) -0.5803(8) 0.36614(11) 0.0667(10) Uani 0.803(8) 1 d G U P A
1
H22A H 0.250852 -0.675901 0.369022 0.08 Uiso 0.803(8) 1 calc R U P A 1
N5A N 0.30236(13) -0.6356(8) 0.33466(10) 0.0633(9) Uani 0.803(8) 1 d G U P A 1
C23A C 0.34241(13) -0.4927(9) 0.33035(9) 0.0668(11) Uani 0.803(8) 1 d G U P A 1
H23A H 0.358939 -0.529773 0.309288 0.08 Uiso 0.803(8) 1 calc R U P A 1
C24A C 0.35775(11) -0.2945(8) 0.35751(10) 0.0623(9) Uani 0.803(8) 1 d G U P A 1
H24A H 0.384548 -0.198869 0.354624 0.075 Uiso 0.803(8) 1 calc R U P A 1
N3B N 0.3570(5) 0.041(3) 0.4255(4) 0.062(2) Uani 0.197(8) 1 d D U P A 2
N4B N 0.3751(5) -0.003(3) 0.4051(5) 0.064(2) Uani 0.197(8) 1 d D U P A 2
N2B N 0.4245(5) 0.645(3) 0.5018(3) 0.045(2) Uani 0.197(8) 1 d G U P A 2
C15B C 0.4462(4) 0.582(3) 0.4689(4) 0.031(2) Uani 0.197(8) 1 d G U P A 2
H15B H 0.473577 0.667155 0.464723 0.037 Uiso 0.197(8) 1 calc R U P A 2
C16B C 0.4269(4) 0.393(3) 0.4422(4) 0.044(2) Uani 0.197(8) 1 d G U P A 2
H16B H 0.441421 0.350783 0.420118 0.053 Uiso 0.197(8) 1 calc R U P A 2
C17B C 0.3860(4) 0.266(3) 0.4484(4) 0.054(3) Uani 0.197(8) 1 d DG U P A 2
C18B C 0.3643(4) 0.329(3) 0.4813(4) 0.060(3) Uani 0.197(8) 1 d G U P A 2
H18B H 0.336936 0.244729 0.485451 0.072 Uiso 0.197(8) 1 calc R U P A 2
C19B C 0.3836(5) 0.519(3) 0.5080(4) 0.057(3) Uani 0.197(8) 1 d G U P A 2
H19B H 0.369092 0.561101 0.530057 0.068 Uiso 0.197(8) 1 calc R U P A 2
C20B C 0.3454(5) -0.227(3) 0.3829(5) 0.065(3) Uani 0.197(8) 1 d DG U P A 2
C21B C 0.3037(5) -0.309(3) 0.3946(4) 0.067(3) Uani 0.197(8) 1 d G U P A 2
H21B H 0.29245 -0.22618 0.416125 0.08 Uiso 0.197(8) 1 calc R U P A 2
C22B C 0.2787(4) -0.513(3) 0.3741(5) 0.068(3) Uani 0.197(8) 1 d G U P A 2
H22B H 0.250786 -0.567538 0.381917 0.081 Uiso 0.197(8) 1 calc R U P A 2
N5B N 0.2955(5) -0.636(3) 0.3419(4) 0.064(3) Uani 0.197(8) 1 d G U P A 2
C23B C 0.3372(6) -0.555(3) 0.3302(4) 0.063(3) Uani 0.197(8) 1 d G U P A 2
H23B H 0.348418 -0.637033 0.308722 0.075 Uiso 0.197(8) 1 calc R U P A 2
C24B C 0.3622(4) -0.350(3) 0.3507(5) 0.068(3) Uani 0.197(8) 1 d G U P A 2
H24B H 0.390082 -0.295674 0.342929 0.082 Uiso 0.197(8) 1 calc R U P A 2
C1 C 0.32519(7) 0.7194(5) 0.67315(7) 0.0569(5) Uani 1 1 d . . . . .
C2 C 0.36003(6) 0.9019(5) 0.68549(6) 0.0529(5) Uani 1 1 d . . . . .
C3 C 0.36038(7) 0.9922(5) 0.72373(6) 0.0541(5) Uani 1 1 d . . . . .
C4 C 0.32796(8) 0.9053(5) 0.74782(7) 0.0604(5) Uani 1 1 d . . . . .
H4 H 0.329016 0.968477 0.773121 0.073 Uiso 1 1 calc R U . . .
C5 C 0.29439(8) 0.7262(5) 0.73427(8) 0.0658(6) Uani 1 1 d . . . . .
H5 H 0.272807 0.667306 0.750502 0.079 Uiso 1 1 calc R U . . .
C6 C 0.29242(8) 0.6338(6) 0.69711(8) 0.0651(6) Uani 1 1 d . . . . .
H6 H 0.26934 0.514516 0.687892 0.078 Uiso 1 1 calc R U . . .
C7 C 0.43754(6) 0.9528(4) 0.66379(6) 0.0490(4) Uani 1 1 d . . . . .
C8 C 0.46480(7) 1.0882(4) 0.63824(6) 0.0494(4) Uani 1 1 d . . . . .
C9 C 0.51073(7) 1.0318(6) 0.64123(7) 0.0631(6) Uani 1 1 d . . . . .
H9 H 0.529067 1.118922 0.624309 0.076 Uiso 1 1 calc R U . . .
C10 C 0.52976(8) 0.8516(7) 0.66839(9) 0.0770(7) Uani 1 1 d . . . . .
H10 H 0.560608 0.817189 0.669756 0.092 Uiso 1 1 calc R U . . .
C11 C 0.50310(9) 0.7216(7) 0.69365(9) 0.0757(7) Uani 1 1 d . . . . .
H11 H 0.515906 0.600096 0.71227 0.091 Uiso 1 1 calc R U . . .
C12 C 0.45718(8) 0.7719(5) 0.69131(7) 0.0624(5) Uani 1 1 d . . . . .
H12 H 0.439269 0.683172 0.708426 0.075 Uiso 1 1 calc R U . . .
C13 C 0.44475(8) 1.2817(5) 0.60736(6) 0.0564(5) Uani 1 1 d . . . . .
H13A H 0.467814 1.406606 0.598922 0.068 Uiso 1 1 calc R U . . .
H13B H 0.421235 1.395063 0.617447 0.068 Uiso 1 1 calc R U . . .
C14 C 0.42535(8) 1.1080(5) 0.57386(6) 0.0572(5) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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
Cl1 C1 1.737(2) . ?
Cl2 C3 1.728(2) . ?
O1 C14 1.318(3) . ?
O1 H1 0.82 . ?
O2 C14 1.201(3) . ?
N1 C2 1.402(3) . ?
N1 C7 1.409(3) . ?
N1 H1A 0.85(3) . ?
N3A N4A 1.283(5) . ?
N3A C17A 1.417(4) . ?
N4A C20A 1.409(3) . ?
N2A C15A 1.39 . ?
N2A C19A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.93 . ?
C16A C17A 1.39 . ?
C16A H16A 0.93 . ?
C17A C18A 1.39 . ?
C18A C19A 1.39 . ?
C18A H18A 0.93 . ?
C19A H19A 0.93 . ?
C20A C21A 1.39 . ?
C20A C24A 1.39 . ?
C21A C22A 1.39 . ?
C21A H21A 0.93 . ?
C22A N5A 1.39 . ?
C22A H22A 0.93 . ?
N5A C23A 1.39 . ?
C23A C24A 1.39 . ?
C23A H23A 0.93 . ?
C24A H24A 0.93 . ?
N3B N4B 0.95(2) . ?
N3B C17B 1.560(16) . ?
N3B C20B 1.97(2) . ?
N4B C20B 1.556(15) . ?
N2B C15B 1.39 . ?
N2B C19B 1.39 . ?
C15B C16B 1.39 . ?
C15B H15B 0.93 . ?
C16B C17B 1.39 . ?
C16B H16B 0.93 . ?
C17B C18B 1.39 . ?
C18B C19B 1.39 . ?
C18B H18B 0.93 . ?
C19B H19B 0.93 . ?
C20B C21B 1.39 . ?
C20B C24B 1.39 . ?
C21B C22B 1.39 . ?
C21B H21B 0.93 . ?
C22B N5B 1.39 . ?
C22B H22B 0.93 . ?
N5B C23B 1.39 . ?
C23B C24B 1.39 . ?
C23B H23B 0.93 . ?
C24B H24B 0.93 . ?
C1 C6 1.391(3) . ?
C1 C2 1.396(3) . ?
C2 C3 1.400(3) . ?
C3 C4 1.388(3) . ?
C4 C5 1.370(4) . ?
C4 H4 0.93 . ?
C5 C6 1.365(4) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C12 1.386(3) . ?
C7 C8 1.405(3) . ?
C8 C9 1.389(3) . ?
C8 C13 1.506(3) . ?
C9 C10 1.369(4) . ?
C9 H9 0.93 . ?
C10 C11 1.375(4) . ?
C10 H10 0.93 . ?
C11 C12 1.384(3) . ?
C11 H11 0.93 . ?
C12 H12 0.93 . ?
C13 C14 1.510(3) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?

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
C14 O1 H1 109.5 . . ?
C2 N1 C7 124.80(18) . . ?
C2 N1 H1A 112(2) . . ?
C7 N1 H1A 116.7(19) . . ?
N4A N3A C17A 114.9(3) . . ?
N3A N4A C20A 115.2(3) . . ?
C15A N2A C19A 120 . . ?
C16A C15A N2A 120 . . ?
C16A C15A H15A 120 . . ?
N2A C15A H15A 120 . . ?
C15A C16A C17A 120 . . ?
C15A C16A H16A 120 . . ?
C17A C16A H16A 120 . . ?
C16A C17A C18A 120 . . ?
C16A C17A N3A 116.3(2) . . ?
C18A C17A N3A 123.7(2) . . ?
C19A C18A C17A 120 . . ?
C19A C18A H18A 120 . . ?
C17A C18A H18A 120 . . ?
C18A C19A N2A 120 . . ?
C18A C19A H19A 120 . . ?
N2A C19A H19A 120 . . ?
C21A C20A C24A 120 . . ?
C21A C20A N4A 117.0(2) . . ?
C24A C20A N4A 123.0(2) . . ?
C22A C21A C20A 120 . . ?
C22A C21A H21A 120 . . ?
C20A C21A H21A 120 . . ?
C21A C22A N5A 120 . . ?
C21A C22A H22A 120 . . ?
N5A C22A H22A 120 . . ?
C23A N5A C22A 120 . . ?
N5A C23A C24A 120 . . ?
N5A C23A H23A 120 . . ?
C24A C23A H23A 120 . . ?
C23A C24A C20A 120 . . ?
C23A C24A H24A 120 . . ?
C20A C24A H24A 120 . . ?
N4B N3B C17B 102.1(18) . . ?
N4B N3B C20B 50.9(15) . . ?
C17B N3B C20B 153.0(12) . . ?
N3B N4B C20B 100.8(19) . . ?
C15B N2B C19B 120 . . ?
C16B C15B N2B 120 . . ?
C16B C15B H15B 120 . . ?
N2B C15B H15B 120 . . ?
C17B C16B C15B 120 . . ?
C17B C16B H16B 120 . . ?
C15B C16B H16B 120 . . ?
C16B C17B C18B 120 . . ?
C16B C17B N3B 132.7(10) . . ?
C18B C17B N3B 107.3(10) . . ?
C19B C18B C17B 120 . . ?
C19B C18B H18B 120 . . ?
C17B C18B H18B 120 . . ?
C18B C19B N2B 120 . . ?
C18B C19B H19B 120 . . ?
N2B C19B H19B 120 . . ?
C21B C20B C24B 120 . . ?
C21B C20B N4B 122.2(12) . . ?
C24B C20B N4B 117.7(12) . . ?
C21B C20B N3B 94.0(9) . . ?
C24B C20B N3B 145.9(9) . . ?
N4B C20B N3B 28.2(8) . . ?
C22B C21B C20B 120 . . ?
C22B C21B H21B 120 . . ?
C20B C21B H21B 120 . . ?
N5B C22B C21B 120 . . ?
N5B C22B H22B 120 . . ?
C21B C22B H22B 120 . . ?
C22B N5B C23B 120 . . ?
C24B C23B N5B 120 . . ?
C24B C23B H23B 120 . . ?
N5B C23B H23B 120 . . ?
C23B C24B C20B 120 . . ?
C23B C24B H24B 120 . . ?
C20B C24B H24B 120 . . ?
C6 C1 C2 122.3(2) . . ?
C6 C1 Cl1 118.68(19) . . ?
C2 C1 Cl1 118.97(17) . . ?
C1 C2 C3 115.96(19) . . ?
C1 C2 N1 121.2(2) . . ?
C3 C2 N1 122.7(2) . . ?
C4 C3 C2 121.9(2) . . ?
C4 C3 Cl2 117.66(19) . . ?
C2 C3 Cl2 120.48(16) . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C12 C7 C8 119.37(19) . . ?
C12 C7 N1 122.03(19) . . ?
C8 C7 N1 118.58(19) . . ?
C9 C8 C7 118.3(2) . . ?
C9 C8 C13 120.51(19) . . ?
C7 C8 C13 121.13(18) . . ?
C10 C9 C8 121.9(2) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C9 C10 C11 119.7(2) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 H11 120 . . ?
C12 C11 H11 120 . . ?
C11 C12 C7 120.8(2) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C8 C13 C14 109.04(18) . . ?
C8 C13 H13A 109.9 . . ?
C14 C13 H13A 109.9 . . ?
C8 C13 H13B 109.9 . . ?
C14 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
O2 C14 O1 123.5(2) . . ?
O2 C14 C13 123.5(2) . . ?
O1 C14 C13 112.94(18) . . ?


####################################################################### 
# 
# 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_diclofenac4-4'-BPEth
_database_code_depnum_ccdc_archive 'CCDC 1909030'
loop_
_audit_author_name
_audit_author_address
'Daniel K. Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-04-09 deposited with the CCDC.	2019-06-07 downloaded from the CCDC.
;

_audit_creation_date             2018-04-04T09:38:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C20 H17 Cl2 N2 O2'
_chemical_formula_weight         388.25

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_Int_Tables_number      60
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   27.525(3)
_cell_length_b                   7.7860(7)
_cell_length_c                   16.8266(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3606.1(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5182
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      26.99

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

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.485
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.43
_exptl_crystal_F_000             1608

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

_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6868
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.978

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_number            22468
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         27.138
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_number_total             3978
_reflns_number_gt                3162
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

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

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

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

_refine_special_details          
;
 The hydrogen atom bound to N1 was allowed to refine its position, but its
 displacement parameter was constrained to -1.2 of the N1 site.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0254P)²+2.2264P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3978
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0751
_refine_ls_wR_factor_gt          0.069
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.051

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.66927(2) 0.78995(6) 0.32126(3) 0.02751(11) Uani 1 d . .
Cl2 Cl 0.63911(2) 1.12446(5) 0.59820(2) 0.02254(11) Uani 1 d . .
O1 O 0.58079(4) 0.50045(15) 0.46392(6) 0.0192(3) Uani 1 d . .
H1 H 0.57422 0.414328 0.435838 0.029 Uiso 1 calc . .
O2 O 0.53254(4) 0.36854(15) 0.55204(7) 0.0219(3) Uani 1 d . .
N1 N 0.63622(5) 0.82171(18) 0.49125(8) 0.0170(3) Uani 1 d . .
H1A H 0.6229(7) 0.755(2) 0.4598(11) 0.02 Uiso 1 d . .
N2 N 0.56314(5) 0.22345(17) 0.38131(8) 0.0172(3) Uani 1 d . .
C1 C 0.67370(6) 0.9744(2) 0.37940(10) 0.0192(3) Uani 1 d . .
C2 C 0.65771(5) 0.9673(2) 0.45830(9) 0.0157(3) Uani 1 d . .
C3 C 0.66170(6) 1.1198(2) 0.50180(10) 0.0169(3) Uani 1 d . .
C4 C 0.68128(6) 1.2683(2) 0.47011(11) 0.0222(4) Uani 1 d . .
H4 H 0.684168 1.368826 0.501753 0.027 Uiso 1 calc . .
C5 C 0.69662(6) 1.2689(2) 0.39177(11) 0.0256(4) Uani 1 d . .
H5 H 0.71007 1.37038 0.369461 0.031 Uiso 1 calc . .
C6 C 0.69247(6) 1.1230(2) 0.34606(11) 0.0252(4) Uani 1 d . .
H6 H 0.702399 1.124243 0.291991 0.03 Uiso 1 calc . .
C7 C 0.65680(6) 0.7373(2) 0.55803(9) 0.0145(3) Uani 1 d . .
C8 C 0.62657(6) 0.63739(19) 0.60630(9) 0.0147(3) Uani 1 d . .
C9 C 0.64736(6) 0.5461(2) 0.66868(9) 0.0165(3) Uani 1 d . .
H9 H 0.627383 0.474743 0.700776 0.02 Uiso 1 calc . .
C10 C 0.69668(6) 0.5570(2) 0.68500(10) 0.0190(3) Uani 1 d . .
H10 H 0.710327 0.492783 0.727499 0.023 Uiso 1 calc . .
C11 C 0.72583(6) 0.6621(2) 0.63897(10) 0.0204(4) Uani 1 d . .
H11 H 0.759429 0.673041 0.650868 0.024 Uiso 1 calc . .
C12 C 0.70607(6) 0.7512(2) 0.57557(10) 0.0180(3) Uani 1 d . .
H12 H 0.726273 0.822472 0.543805 0.022 Uiso 1 calc . .
C13 C 0.57243(6) 0.6284(2) 0.59072(9) 0.0174(3) Uani 1 d . .
H13A H 0.555196 0.610185 0.641673 0.021 Uiso 1 calc . .
H13B H 0.561362 0.739289 0.568342 0.021 Uiso 1 calc . .
C14 C 0.55930(5) 0.4854(2) 0.53385(9) 0.0159(3) Uani 1 d . .
C15 C 0.57196(6) 0.2067(2) 0.30351(9) 0.0192(4) Uani 1 d . .
H15 H 0.58534 0.301845 0.275724 0.023 Uiso 1 calc . .
C16 C 0.56254(6) 0.0578(2) 0.26163(9) 0.0183(3) Uani 1 d . .
H16 H 0.569305 0.051899 0.206338 0.022 Uiso 1 calc . .
C17 C 0.54311(6) -0.0833(2) 0.30087(9) 0.0159(3) Uani 1 d . .
C18 C 0.53526(6) -0.0673(2) 0.38217(9) 0.0169(3) Uani 1 d . .
H18 H 0.522961 -0.161653 0.411788 0.02 Uiso 1 calc . .
C19 C 0.54542(6) 0.0860(2) 0.41958(10) 0.0176(3) Uani 1 d . .
H19 H 0.539595 0.094765 0.475079 0.021 Uiso 1 calc . .
C20 C 0.52776(6) -0.2430(2) 0.25721(10) 0.0182(3) Uani 1 d . .
H20A H 0.53686 -0.345481 0.288693 0.022 Uiso 1 calc . .
H20B H 0.544927 -0.249066 0.205589 0.022 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   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
Cl1 C1 1.7421(18) . ?
Cl2 C3 1.7376(17) . ?
O1 C14 1.3223(18) . ?
O1 H1 0.84 . ?
O2 C14 1.2098(19) . ?
N1 C2 1.394(2) . ?
N1 C7 1.420(2) . ?
N1 H1A 0.830(19) . ?
N2 C15 1.338(2) . ?
N2 C19 1.341(2) . ?
C1 C6 1.386(2) . ?
C1 C2 1.400(2) . ?
C2 C3 1.399(2) . ?
C3 C4 1.383(2) . ?
C4 C5 1.384(3) . ?
C4 H4 0.95 . ?
C5 C6 1.376(3) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C12 1.392(2) . ?
C7 C8 1.399(2) . ?
C8 C9 1.391(2) . ?
C8 C13 1.515(2) . ?
C9 C10 1.388(2) . ?
C9 H9 0.95 . ?
C10 C11 1.383(2) . ?
C10 H10 0.95 . ?
C11 C12 1.384(2) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
C13 C14 1.512(2) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C15 C16 1.382(2) . ?
C15 H15 0.95 . ?
C16 C17 1.389(2) . ?
C16 H16 0.95 . ?
C17 C18 1.390(2) . ?
C17 C20 1.505(2) . ?
C18 C19 1.379(2) . ?
C18 H18 0.95 . ?
C19 H19 0.95 . ?
C20 C20 1.547(3) 3_655 ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?

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
C14 O1 H1 109.5 . . ?
C2 N1 C7 121.49(14) . . ?
C2 N1 H1A 116.5(13) . . ?
C7 N1 H1A 112.9(13) . . ?
C15 N2 C19 117.29(14) . . ?
C6 C1 C2 122.29(16) . . ?
C6 C1 Cl1 119.15(13) . . ?
C2 C1 Cl1 118.55(13) . . ?
N1 C2 C3 121.02(14) . . ?
N1 C2 C1 122.89(15) . . ?
C3 C2 C1 115.97(15) . . ?
C4 C3 C2 122.58(15) . . ?
C4 C3 Cl2 118.81(13) . . ?
C2 C3 Cl2 118.57(12) . . ?
C3 C4 C5 119.27(17) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 120.28(16) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 119.58(16) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C12 C7 C8 120.00(14) . . ?
C12 C7 N1 121.34(14) . . ?
C8 C7 N1 118.66(14) . . ?
C9 C8 C7 118.52(14) . . ?
C9 C8 C13 120.78(14) . . ?
C7 C8 C13 120.70(14) . . ?
C10 C9 C8 121.37(15) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C11 C10 C9 119.54(15) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.02(15) . . ?
C10 C11 H11 120 . . ?
C12 C11 H11 120 . . ?
C11 C12 C7 120.46(15) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C14 C13 C8 112.25(13) . . ?
C14 C13 H13A 109.2 . . ?
C8 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C8 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
O2 C14 O1 124.36(15) . . ?
O2 C14 C13 122.62(14) . . ?
O1 C14 C13 113.01(13) . . ?
N2 C15 C16 123.14(15) . . ?
N2 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C15 C16 C17 119.59(15) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C18 117.18(15) . . ?
C16 C17 C20 121.98(15) . . ?
C18 C17 C20 120.70(14) . . ?
C19 C18 C17 119.68(15) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
N2 C19 C18 123.07(15) . . ?
N2 C19 H19 118.5 . . ?
C18 C19 H19 118.5 . . ?
C17 C20 C20 110.73(11) . 3_655 ?
C17 C20 H20A 109.5 . . ?
C20 C20 H20A 109.5 3_655 . ?
C17 C20 H20B 109.5 . . ?
C20 C20 H20B 109.5 3_655 . ?
H20A C20 H20B 108.1 . . ?

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
O1 H1 N2 0.84 1.77 2.6115(18) 175.8 .
N1 H1A O1 0.830(19) 2.294(19) 2.9658(18) 138.3(16) .

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_diclofenac4-4'-BIPY
_database_code_depnum_ccdc_archive 'CCDC 1909032'
loop_
_audit_author_name
_audit_author_address
'Daniel K. Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-04-09 deposited with the CCDC.	2019-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT242_diclofenac4-4'-BIPY 
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of        C31 Check 
RESPONSE: The 4,4'-dipyridine molecule rotates slightly about an axis consisting
          of C31, N3, and their symmetry equivalents. Attempts to split atom sites 
          C29, C30, C32, and C33 did not improve the model.  
;
_vrf_PLAT250_diclofenac4-4'-BIPY 
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.4 Note  
RESPONSE: This is due to the positional disorder of the 1,3-dichlorobenzene
          moieties within the structure. Even though the sites were split and 
          restrained, the anisotropic displacement ellipsoid values for the 
          sites were still elongated.
;
_vrf_PLAT911_diclofenac4-4'-BIPY 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report
RESPONSE: These reflections were not collected using only omega scans.
;
# end Validation Reply Form

_audit_creation_date             2018-09-13T10:08:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C38 H30 Cl4 N4 O4'
_chemical_formula_weight         748.46

#----------------------------------------------------------------------------#
#                   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                   8.6025(16)
_cell_length_b                   14.743(3)
_cell_length_c                   15.818(3)
_cell_angle_alpha                113.957(3)
_cell_angle_beta                 90.600(3)
_cell_angle_gamma                105.072(3)
_cell_volume                     1754.9(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9967
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      22.66

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

_exptl_crystal_description       blocky
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             772

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

_exptl_absorpt_coefficient_mu    0.385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7079
_shelx_estimated_absorpt_T_min   0.837
_shelx_estimated_absorpt_T_max   0.91

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

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_number            40056
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.421
_diffrn_reflns_theta_max         27.284
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             7844
_reflns_number_gt                5331
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

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

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

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

_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+0.2719P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7844
_refine_ls_number_parameters     605
_refine_ls_number_restraints     268
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1155
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.043

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

_refine_special_details          
;
The 1,3-dichorobenzene moieties were both positionally disordered over two 
sites (A and B) and were allowed to free refine their occupancies to a total 
value of 1. This resulted in site occupancies of 0.52 and 0.48, respectively.
To help restrain the anisotropic displacement ellipsoids of the disordered
sites, SIMU and DELU restraints were applied with varying tolerences. Also,
the N-C bond lengths of disordered sites were restrained with a free variable
DFIX command, which resulted in an average distance of 1.397(11) Å. 
;

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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 0.58486(14) 0.21482(11) 0.80658(8) 0.0495(3) Uani 1 1 d . . . . .
H1A H 0.512452 0.187057 0.760319 0.074 Uiso 1 1 calc R U . . .
O2 O 0.74117(16) 0.16150(13) 0.69753(9) 0.0666(4) Uani 1 1 d . . . . .
O3 O 0.92703(14) 0.39670(11) 0.68681(8) 0.0498(3) Uani 1 1 d . . . . .
H3 H 0.88343 0.421621 0.734931 0.075 Uiso 1 1 calc R U . . .
O4 O 1.10783(15) 0.39644(11) 0.78804(8) 0.0543(3) Uani 1 1 d . . . . .
N1 N 0.64198(18) 0.25100(11) 1.00069(10) 0.0400(3) Uani 1 1 d D . . . .
H1B H 0.606(2) 0.2558(14) 0.9535(13) 0.048 Uiso 1 1 d . U . . .
N2 N 0.87747(18) 0.26092(12) 0.48718(10) 0.0438(4) Uani 1 1 d D . . . .
H2B H 0.839(2) 0.2824(15) 0.5405(14) 0.053 Uiso 1 1 d . U . . .
N3 N 0.34224(17) 0.12463(12) 0.67423(10) 0.0455(4) Uani 1 1 d . . . . .
N4 N 0.76043(17) 0.46310(12) 0.82454(10) 0.0444(4) Uani 1 1 d . . . . .
Cl1A Cl 0.2922(7) 0.2240(5) 0.9640(5) 0.0703(11) Uani 0.520(11) 1 d . U P A 1
Cl2A Cl 0.8527(4) 0.3266(4) 1.1825(3) 0.0630(6) Uani 0.520(11) 1 d . U P A 1
C1A C 0.3971(14) 0.2625(13) 1.0726(7) 0.0528(18) Uani 0.520(11) 1 d . U P A 1
C2A C 0.5616(12) 0.2660(15) 1.0783(8) 0.039(2) Uani 0.520(11) 1 d D U P A 1
C3A C 0.6438(9) 0.3024(11) 1.1666(7) 0.0477(16) Uani 0.520(11) 1 d . U P A 1
C4A C 0.5644(9) 0.3231(8) 1.2449(6) 0.0647(17) Uani 0.520(11) 1 d . U P A 1
H4A H 0.621903 0.343979 1.304433 0.078 Uiso 0.520(11) 1 calc R U P A 1
C5A C 0.4002(11) 0.3130(7) 1.2352(6) 0.0705(19) Uani 0.520(11) 1 d . U P A 1
H5A H 0.344804 0.326426 1.288684 0.085 Uiso 0.520(11) 1 calc R U P A 1
C6A C 0.3165(9) 0.2844(7) 1.1510(7) 0.0661(18) Uani 0.520(11) 1 d . U P A 1
H6A H 0.204162 0.279356 1.145608 0.079 Uiso 0.520(11) 1 calc R U P A 1
Cl1B Cl 0.2912(7) 0.2182(5) 0.9386(3) 0.0571(7) Uani 0.480(11) 1 d . U P A 2
Cl2B Cl 0.8003(9) 0.3288(4) 1.1956(3) 0.0803(11) Uani 0.480(11) 1 d . U P A 2
C1B C 0.3726(14) 0.2564(14) 1.0523(7) 0.0462(17) Uani 0.480(11) 1 d . U P A 2
C2B C 0.5390(15) 0.2739(17) 1.0716(8) 0.039(2) Uani 0.480(11) 1 d D U P A 2
C3B C 0.5960(12) 0.3037(12) 1.1655(8) 0.0551(18) Uani 0.480(11) 1 d . U P A 2
C4B C 0.4922(15) 0.3121(7) 1.2332(6) 0.068(2) Uani 0.480(11) 1 d . U P A 2
H4B H 0.533505 0.328619 1.295298 0.082 Uiso 0.480(11) 1 calc R U P A 2
C5B C 0.3298(14) 0.2964(7) 1.2104(7) 0.070(2) Uani 0.480(11) 1 d . U P A 2
H5B H 0.259365 0.303636 1.257088 0.084 Uiso 0.480(11) 1 calc R U P A 2
C6B C 0.2683(12) 0.2702(7) 1.1194(6) 0.0602(17) Uani 0.480(11) 1 d . U P A 2
H6B H 0.15702 0.261802 1.103609 0.072 Uiso 0.480(11) 1 calc R U P A 2
C7 C 0.71635(19) 0.16946(12) 0.97307(11) 0.0361(4) Uani 1 1 d . . . . .
C8 C 0.81910(18) 0.16020(12) 0.90384(11) 0.0362(4) Uani 1 1 d . . . . .
C9 C 0.8872(2) 0.07852(14) 0.87506(13) 0.0458(4) Uani 1 1 d . . . . .
H9 H 0.954706 0.070596 0.826938 0.055 Uiso 1 1 calc R U . . .
C10 C 0.8598(2) 0.00886(15) 0.91418(14) 0.0521(5) Uani 1 1 d . . . . .
H10 H 0.909111 -0.045782 0.894054 0.062 Uiso 1 1 calc R U . . .
C11 C 0.7599(2) 0.01918(14) 0.98294(14) 0.0510(5) Uani 1 1 d . . . . .
H11 H 0.740388 -0.028583 1.010462 0.061 Uiso 1 1 calc R U . . .
C12 C 0.6879(2) 0.09869(13) 1.01219(12) 0.0438(4) Uani 1 1 d . . . . .
H12 H 0.618546 0.104862 1.059329 0.053 Uiso 1 1 calc R U . . .
C13 C 0.8533(2) 0.23472(14) 0.85882(12) 0.0419(4) Uani 1 1 d . . . . .
H13A H 0.96026 0.237951 0.835805 0.05 Uiso 1 1 calc R U . . .
H13B H 0.857311 0.304985 0.905599 0.05 Uiso 1 1 calc R U . . .
C14 C 0.7230(2) 0.20045(14) 0.77853(12) 0.0416(4) Uani 1 1 d . . . . .
Cl3A Cl 0.9794(9) 0.1284(5) 0.3077(3) 0.0823(11) Uani 0.520(11) 1 d . U P A 1
Cl4A Cl 0.5437(5) 0.2648(3) 0.5357(3) 0.0690(8) Uani 0.520(11) 1 d . U P A 1
C15A C 0.7842(11) 0.1342(11) 0.3252(9) 0.0609(17) Uani 0.520(11) 1 d . U P A 1
C16A C 0.7545(16) 0.1975(16) 0.4131(8) 0.0482(17) Uani 0.520(11) 1 d D U P A 1
C17A C 0.5926(13) 0.1935(9) 0.4270(6) 0.0594(16) Uani 0.520(11) 1 d . U P A 1
C18A C 0.4689(11) 0.1326(7) 0.3563(6) 0.0728(17) Uani 0.520(11) 1 d . U P A 1
H18A H 0.359597 0.129288 0.36716 0.087 Uiso 0.520(11) 1 calc R U P A 1
C19A C 0.5033(11) 0.0759(7) 0.2691(7) 0.0784(19) Uani 0.520(11) 1 d . U P A 1
H19A H 0.416321 0.036683 0.219627 0.094 Uiso 0.520(11) 1 calc R U P A 1
C20A C 0.6561(12) 0.0737(7) 0.2509(6) 0.0742(18) Uani 0.520(11) 1 d . U P A 1
H20A H 0.676636 0.032958 0.190302 0.089 Uiso 0.520(11) 1 calc R U P A 1
Cl3B Cl 1.0221(6) 0.1427(5) 0.3186(4) 0.0799(11) Uani 0.480(11) 1 d . U P A 2
Cl4B Cl 0.5285(6) 0.2452(4) 0.5031(6) 0.1045(14) Uani 0.480(11) 1 d . U P A 2
C15B C 0.8216(11) 0.1382(12) 0.3222(10) 0.0550(17) Uani 0.480(11) 1 d . U P A 2
C16B C 0.7691(16) 0.1983(17) 0.4059(10) 0.047(2) Uani 0.480(11) 1 d D U P A 2
C17B C 0.5997(13) 0.1795(9) 0.4024(6) 0.0561(18) Uani 0.480(11) 1 d . U P A 2
C18B C 0.4888(10) 0.1098(7) 0.3222(7) 0.0685(18) Uani 0.480(11) 1 d . U P A 2
H18B H 0.375126 0.099306 0.322862 0.082 Uiso 0.480(11) 1 calc R U P A 2
C19B C 0.5502(12) 0.0575(7) 0.2427(6) 0.0710(18) Uani 0.480(11) 1 d . U P A 2
H19B H 0.478267 0.010984 0.187169 0.085 Uiso 0.480(11) 1 calc R U P A 2
C20B C 0.7169(10) 0.0720(8) 0.2428(7) 0.0691(18) Uani 0.480(11) 1 d . U P A 2
H20B H 0.757909 0.035731 0.18736 0.083 Uiso 0.480(11) 1 calc R U P A 2
C21 C 1.01494(19) 0.33853(13) 0.48574(11) 0.0364(4) Uani 1 1 d . . . . .
C22 C 1.1470(2) 0.37617(14) 0.55466(11) 0.0407(4) Uani 1 1 d . . . . .
C23 C 1.2810(2) 0.45186(16) 0.55380(14) 0.0529(5) Uani 1 1 d . . . . .
H23 H 1.372175 0.477913 0.600127 0.064 Uiso 1 1 calc R U . . .
C24 C 1.2853(2) 0.49006(16) 0.48782(16) 0.0585(5) Uani 1 1 d . . . . .
H24 H 1.378507 0.542121 0.488763 0.07 Uiso 1 1 calc R U . . .
C25 C 1.1538(3) 0.45270(15) 0.41987(14) 0.0531(5) Uani 1 1 d . . . . .
H25 H 1.156073 0.478826 0.373855 0.064 Uiso 1 1 calc R U . . .
C26 C 1.0187(2) 0.37703(14) 0.41928(12) 0.0425(4) Uani 1 1 d . . . . .
H26 H 0.927905 0.351351 0.372786 0.051 Uiso 1 1 calc R U . . .
C27 C 1.1479(2) 0.33524(17) 0.62735(12) 0.0516(5) Uani 1 1 d . . . . .
H27A H 1.262311 0.34808 0.650831 0.062 Uiso 1 1 calc R U . . .
H27B H 1.097996 0.259196 0.596952 0.062 Uiso 1 1 calc R U . . .
C28 C 1.0614(2) 0.38013(14) 0.70963(12) 0.0418(4) Uani 1 1 d . . . . .
C29 C 0.3513(2) 0.06038(17) 0.58871(14) 0.0578(5) Uani 1 1 d . . . . .
H29 H 0.453205 0.048384 0.574523 0.069 Uiso 1 1 calc R U . . .
C30 C 0.2224(2) 0.00974(16) 0.51887(14) 0.0558(5) Uani 1 1 d . . . . .
H30 H 0.236405 -0.03582 0.45844 0.067 Uiso 1 1 calc R U . . .
C31 C 0.07138(19) 0.02520(13) 0.53667(12) 0.0379(4) Uani 1 1 d . . . . .
C32 C 0.0620(2) 0.09086(17) 0.62716(13) 0.0547(5) Uani 1 1 d . . . . .
H32 H -0.038697 0.103068 0.644259 0.066 Uiso 1 1 calc R U . . .
C33 C 0.1979(2) 0.13845(18) 0.69234(13) 0.0584(5) Uani 1 1 d . . . . .
H33 H 0.187983 0.183781 0.753788 0.07 Uiso 1 1 calc R U . . .
C34 C 0.6015(2) 0.44414(17) 0.80465(13) 0.0561(5) Uani 1 1 d . . . . .
H34 H 0.558124 0.419386 0.741235 0.067 Uiso 1 1 calc R U . . .
C35 C 0.4963(2) 0.45824(16) 0.87035(12) 0.0493(5) Uani 1 1 d . . . . .
H35 H 0.383982 0.444372 0.852169 0.059 Uiso 1 1 calc R U . . .
C36 C 0.55494(19) 0.49279(12) 0.96326(11) 0.0347(4) Uani 1 1 d . . . . .
C37 C 0.7208(2) 0.51354(15) 0.98393(12) 0.0472(4) Uani 1 1 d . . . . .
H37 H 0.768043 0.538424 1.04665 0.057 Uiso 1 1 calc R U . . .
C38 C 0.8169(2) 0.49802(15) 0.91340(12) 0.0486(5) Uani 1 1 d . . . . .
H38 H 0.930394 0.513272 0.929495 0.058 Uiso 1 1 calc R U . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C14 1.311(2) . ?
O1 H1A 0.84 . ?
O2 C14 1.204(2) . ?
O3 C28 1.317(2) . ?
O3 H3 0.84 . ?
O4 C28 1.206(2) . ?
N1 C2A 1.382(11) . ?
N1 C7 1.423(2) . ?
N1 C2B 1.423(11) . ?
N1 H1B 0.841(19) . ?
N2 C16A 1.392(11) . ?
N2 C16B 1.392(12) . ?
N2 C21 1.423(2) . ?
N2 H2B 0.873(19) . ?
N3 C29 1.317(2) . ?
N3 C33 1.326(2) . ?
N4 C38 1.321(2) . ?
N4 C34 1.330(2) . ?
Cl1A C1A 1.731(8) . ?
Cl2A C3A 1.733(6) . ?
C1A C6A 1.389(13) . ?
C1A C2A 1.403(13) . ?
C2A C3A 1.384(12) . ?
C3A C4A 1.382(10) . ?
C4A C5A 1.382(8) . ?
C4A H4A 0.95 . ?
C5A C6A 1.355(10) . ?
C5A H5A 0.95 . ?
C6A H6A 0.95 . ?
Cl1B C1B 1.728(8) . ?
Cl2B C3B 1.718(8) . ?
C1B C6B 1.384(12) . ?
C1B C2B 1.394(13) . ?
C2B C3B 1.408(14) . ?
C3B C4B 1.390(12) . ?
C4B C5B 1.375(10) . ?
C4B H4B 0.95 . ?
C5B C6B 1.388(10) . ?
C5B H5B 0.95 . ?
C6B H6B 0.95 . ?
C7 C12 1.388(2) . ?
C7 C8 1.400(2) . ?
C8 C9 1.389(2) . ?
C8 C13 1.508(2) . ?
C9 C10 1.374(3) . ?
C9 H9 0.95 . ?
C10 C11 1.377(3) . ?
C10 H10 0.95 . ?
C11 C12 1.384(2) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
C13 C14 1.510(2) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
Cl3A C15A 1.724(9) . ?
Cl4A C17A 1.736(8) . ?
C15A C16A 1.395(15) . ?
C15A C20A 1.414(11) . ?
C16A C17A 1.402(15) . ?
C17A C18A 1.361(9) . ?
C18A C19A 1.374(9) . ?
C18A H18A 0.95 . ?
C19A C20A 1.355(10) . ?
C19A H19A 0.95 . ?
C20A H20A 0.95 . ?
Cl3B C15B 1.712(9) . ?
Cl4B C17B 1.709(8) . ?
C15B C20B 1.366(12) . ?
C15B C16B 1.418(16) . ?
C16B C17B 1.407(15) . ?
C17B C18B 1.408(10) . ?
C18B C19B 1.376(10) . ?
C18B H18B 0.95 . ?
C19B C20B 1.394(10) . ?
C19B H19B 0.95 . ?
C20B H20B 0.95 . ?
C21 C26 1.380(2) . ?
C21 C22 1.393(2) . ?
C22 C23 1.385(3) . ?
C22 C27 1.501(3) . ?
C23 C24 1.369(3) . ?
C23 H23 0.95 . ?
C24 C25 1.382(3) . ?
C24 H24 0.95 . ?
C25 C26 1.383(3) . ?
C25 H25 0.95 . ?
C26 H26 0.95 . ?
C27 C28 1.505(2) . ?
C27 H27A 0.99 . ?
C27 H27B 0.99 . ?
C29 C30 1.372(3) . ?
C29 H29 0.95 . ?
C30 C31 1.389(2) . ?
C30 H30 0.95 . ?
C31 C32 1.382(3) . ?
C31 C31 1.484(3) 2_556 ?
C32 C33 1.372(3) . ?
C32 H32 0.95 . ?
C33 H33 0.95 . ?
C34 C35 1.372(2) . ?
C34 H34 0.95 . ?
C35 C36 1.384(2) . ?
C35 H35 0.95 . ?
C36 C37 1.385(2) . ?
C36 C36 1.489(3) 2_667 ?
C37 C38 1.375(2) . ?
C37 H37 0.95 . ?
C38 H38 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O1 H1A 109.5 . . ?
C28 O3 H3 109.5 . . ?
C2A N1 C7 116.3(8) . . ?
C7 N1 C2B 126.4(8) . . ?
C2A N1 H1B 122.6(14) . . ?
C7 N1 H1B 110.2(13) . . ?
C2B N1 H1B 111.0(14) . . ?
C16A N2 C21 125.2(8) . . ?
C16B N2 C21 119.1(9) . . ?
C16A N2 H2B 112.0(14) . . ?
C16B N2 H2B 118.9(14) . . ?
C21 N2 H2B 110.9(13) . . ?
C29 N3 C33 116.66(16) . . ?
C38 N4 C34 116.56(15) . . ?
C6A C1A C2A 121.5(7) . . ?
C6A C1A Cl1A 120.0(8) . . ?
C2A C1A Cl1A 118.4(9) . . ?
N1 C2A C3A 121.8(8) . . ?
N1 C2A C1A 120.4(8) . . ?
C3A C2A C1A 116.8(8) . . ?
C4A C3A C2A 121.8(7) . . ?
C4A C3A Cl2A 117.9(6) . . ?
C2A C3A Cl2A 120.3(7) . . ?
C5A C4A C3A 119.1(7) . . ?
C5A C4A H4A 120.5 . . ?
C3A C4A H4A 120.5 . . ?
C6A C5A C4A 121.3(7) . . ?
C6A C5A H5A 119.4 . . ?
C4A C5A H5A 119.4 . . ?
C5A C6A C1A 119.2(6) . . ?
C5A C6A H6A 120.4 . . ?
C1A C6A H6A 120.4 . . ?
C6B C1B C2B 123.8(8) . . ?
C6B C1B Cl1B 117.6(8) . . ?
C2B C1B Cl1B 118.6(8) . . ?
C1B C2B C3B 115.3(9) . . ?
C1B C2B N1 122.9(8) . . ?
C3B C2B N1 121.3(8) . . ?
C4B C3B C2B 122.0(8) . . ?
C4B C3B Cl2B 119.7(8) . . ?
C2B C3B Cl2B 118.3(8) . . ?
C5B C4B C3B 120.0(7) . . ?
C5B C4B H4B 120 . . ?
C3B C4B H4B 120 . . ?
C4B C5B C6B 120.2(7) . . ?
C4B C5B H5B 119.9 . . ?
C6B C5B H5B 119.9 . . ?
C1B C6B C5B 118.5(7) . . ?
C1B C6B H6B 120.7 . . ?
C5B C6B H6B 120.7 . . ?
C12 C7 C8 119.56(15) . . ?
C12 C7 N1 121.64(15) . . ?
C8 C7 N1 118.79(15) . . ?
C9 C8 C7 118.53(16) . . ?
C9 C8 C13 119.83(15) . . ?
C7 C8 C13 121.62(15) . . ?
C10 C9 C8 121.88(17) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C9 C10 C11 119.20(17) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C12 120.42(17) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 120.40(17) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C8 C13 C14 110.43(14) . . ?
C8 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
C8 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
O2 C14 O1 123.23(16) . . ?
O2 C14 C13 124.27(16) . . ?
O1 C14 C13 112.47(15) . . ?
C16A C15A C20A 121.0(8) . . ?
C16A C15A Cl3A 119.4(8) . . ?
C20A C15A Cl3A 119.6(8) . . ?
N2 C16A C15A 122.8(10) . . ?
N2 C16A C17A 119.4(10) . . ?
C15A C16A C17A 117.8(9) . . ?
C18A C17A C16A 121.2(7) . . ?
C18A C17A Cl4A 117.9(7) . . ?
C16A C17A Cl4A 120.9(7) . . ?
C17A C18A C19A 119.5(7) . . ?
C17A C18A H18A 120.2 . . ?
C19A C18A H18A 120.2 . . ?
C20A C19A C18A 122.7(7) . . ?
C20A C19A H19A 118.7 . . ?
C18A C19A H19A 118.7 . . ?
C19A C20A C15A 117.7(7) . . ?
C19A C20A H20A 121.1 . . ?
C15A C20A H20A 121.1 . . ?
C20B C15B C16B 122.7(8) . . ?
C20B C15B Cl3B 116.9(8) . . ?
C16B C15B Cl3B 120.3(9) . . ?
N2 C16B C17B 123.6(10) . . ?
N2 C16B C15B 121.3(10) . . ?
C17B C16B C15B 114.6(9) . . ?
C16B C17B C18B 123.8(8) . . ?
C16B C17B Cl4B 116.8(8) . . ?
C18B C17B Cl4B 119.5(7) . . ?
C19B C18B C17B 117.9(7) . . ?
C19B C18B H18B 121 . . ?
C17B C18B H18B 121 . . ?
C18B C19B C20B 120.6(7) . . ?
C18B C19B H19B 119.7 . . ?
C20B C19B H19B 119.7 . . ?
C15B C20B C19B 120.3(7) . . ?
C15B C20B H20B 119.9 . . ?
C19B C20B H20B 119.9 . . ?
C26 C21 C22 120.26(16) . . ?
C26 C21 N2 121.77(15) . . ?
C22 C21 N2 117.96(15) . . ?
C23 C22 C21 118.26(17) . . ?
C23 C22 C27 119.99(16) . . ?
C21 C22 C27 121.73(16) . . ?
C24 C23 C22 121.63(18) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C23 C24 C25 119.82(18) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C26 119.56(18) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C21 C26 C25 120.46(17) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C22 C27 C28 116.03(15) . . ?
C22 C27 H27A 108.3 . . ?
C28 C27 H27A 108.3 . . ?
C22 C27 H27B 108.3 . . ?
C28 C27 H27B 108.3 . . ?
H27A C27 H27B 107.4 . . ?
O4 C28 O3 123.45(16) . . ?
O4 C28 C27 123.35(16) . . ?
O3 C28 C27 113.16(14) . . ?
N3 C29 C30 123.90(17) . . ?
N3 C29 H29 118 . . ?
C30 C29 H29 118 . . ?
C29 C30 C31 119.88(18) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C32 C31 C30 115.85(16) . . ?
C32 C31 C31 121.84(19) . 2_556 ?
C30 C31 C31 122.3(2) . 2_556 ?
C33 C32 C31 120.12(17) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
N3 C33 C32 123.57(18) . . ?
N3 C33 H33 118.2 . . ?
C32 C33 H33 118.2 . . ?
N4 C34 C35 123.85(17) . . ?
N4 C34 H34 118.1 . . ?
C35 C34 H34 118.1 . . ?
C34 C35 C36 119.63(16) . . ?
C34 C35 H35 120.2 . . ?
C36 C35 H35 120.2 . . ?
C35 C36 C37 116.40(15) . . ?
C35 C36 C36 121.55(18) . 2_667 ?
C37 C36 C36 122.05(18) . 2_667 ?
C38 C37 C36 119.81(16) . . ?
C38 C37 H37 120.1 . . ?
C36 C37 H37 120.1 . . ?
N4 C38 C37 123.73(16) . . ?
N4 C38 H38 118.1 . . ?
C37 C38 H38 118.1 . . ?

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
O1 H1A N3 0.84 1.76 2.5906(18) 171.8 .
O3 H3 N4 0.84 1.78 2.6119(18) 170.6 .
N1 H1B O1 0.841(19) 2.143(19) 2.9079(19) 151.1(17) .
N2 H2B O3 0.873(19) 2.21(2) 2.9249(19) 138.5(16) .
N2 H2B Cl4A 0.873(19) 2.486(19) 2.988(4) 117.3(15) .



# END of CIF
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
