#------------------------------------------------------------------------------
#$Date: 2019-06-08 03:06:56 +0300 (Sat, 08 Jun 2019) $
#$Revision: 215762 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/36/7123614.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7123614
loop_
_publ_author_name
'Zheng, Qixuan'
'Rood, Samantha L.'
'Unruh, Daniel K.'
'Hutchins, Kristin M.'
_publ_section_title
;
 Unique supramolecular complex of diclofenac: structural robustness,
 crystal-to-crystal solvent exchange, and mechanochemical synthesis
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC03946E
_journal_year                    2019
_chemical_formula_sum            'C47 H40 Cl4 N4 O4'
_chemical_formula_weight         866.63
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-04-03T10:33:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2019-04-09 deposited with the CCDC.    2019-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.447(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.763(2)
_cell_length_b                   7.0061(8)
_cell_length_c                   30.454(4)
_cell_measurement_reflns_used    8456
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.30
_cell_volume                     4159.5(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            23563
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.165
_diffrn_reflns_theta_min         1.356
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       blade
_exptl_crystal_F_000             1800
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.485
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4604
_refine_ls_number_restraints     260
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0320P)²+4.9478P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0779
_reflns_number_gt                3966
_reflns_number_total             4604
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc03946e2.cif
_cod_data_source_block           diclofenac4-4'-BPE
_cod_original_cell_volume        4159.4(8)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7123614
_shelx_estimated_absorpt_t_min   0.854
_shelx_estimated_absorpt_t_max   0.969
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'
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
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_
_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
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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_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
