#------------------------------------------------------------------------------
#$Date: 2019-11-07 22:08:37 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223711 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/32/7233281.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_7233281
loop_
_publ_author_name
'Wang, Xinyi'
'Xu, Shijie'
'Jia, Lina'
'Yang, Yujia'
'Liu, Yu'
'Gong, Junbo'
'Wu, Songgu'
_publ_section_title
;
 Drug--drug salts of mefenamic acid\tolfenamic acid and piperazine to
 improve physicochemical properties for potential veterinary use
;
_journal_issue                   35
_journal_name_full               CrystEngComm
_journal_page_first              5284
_journal_paper_doi               10.1039/C9CE00781D
_journal_volume                  21
_journal_year                    2019
_chemical_formula_sum            'C32 H34 Cl2 N4 O4'
_chemical_formula_weight         609.53
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc22c7yn
_audit_creation_method           SHELXL-2014/8
_audit_update_record
;
2019-07-01 deposited with the CCDC.    2019-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.303(2)
_cell_length_b                   7.6173(15)
_cell_length_c                   38.517(8)
_cell_measurement_reflns_used    3961
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.5204
_cell_measurement_theta_min      2.0461
_cell_volume                     3022.9(10)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'ShelXL (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            13183
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.018
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_min         2.115
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            transparent
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       prism
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2604
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0634
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0704P)²+2.6772P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1529
_refine_ls_wR_factor_ref         0.1634
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2235
_reflns_number_total             2604
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00781d2.cif
_cod_data_source_block           R20180426D1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7233278--7233281.cif.
;
_cod_database_code               7233281
_shelx_shelxl_version_number     2014/8
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.950
_shelx_estimated_absorpt_t_max   0.970
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
Cl1 Cl 0.34332(9) 0.99670(16) 0.70274(2) 0.0599(4) Uani 1 1 d . .
O1 O 0.7068(2) 0.9038(3) 0.55737(5) 0.0358(5) Uani 1 1 d . .
O2 O 0.86676(19) 0.9549(2) 0.51891(4) 0.0280(5) Uani 1 1 d . .
N1 N 0.7510(3) 0.9578(3) 0.62448(6) 0.0315(6) Uani 1 1 d D .
H1 H 0.702(3) 0.931(4) 0.6062(5) 0.038 Uiso 1 1 d D U
C1 C 0.4855(3) 1.0554(4) 0.63269(8) 0.0384(8) Uani 1 1 d . .
H1A H 0.5427 1.1280 0.6183 0.058 Uiso 1 1 calc R U
H1B H 0.4155 1.1282 0.6421 0.058 Uiso 1 1 calc R U
H1C H 0.4484 0.9612 0.6185 0.058 Uiso 1 1 calc R U
C2 C 0.5633(3) 0.9758(4) 0.66242(7) 0.0284(7) Uani 1 1 d . .
C3 C 0.5075(3) 0.9416(4) 0.69515(7) 0.0352(7) Uani 1 1 d . .
C4 C 0.5763(4) 0.8643(4) 0.72246(7) 0.0429(8) Uani 1 1 d . .
H4 H 0.5356 0.8436 0.7442 0.052 Uiso 1 1 calc R U
C5 C 0.7060(3) 0.8183(4) 0.71716(7) 0.0394(8) Uani 1 1 d . .
H5 H 0.7537 0.7647 0.7354 0.047 Uiso 1 1 calc R U
C6 C 0.7667(3) 0.8503(4) 0.68515(7) 0.0300(7) Uani 1 1 d . .
H6 H 0.8550 0.8187 0.6818 0.036 Uiso 1 1 calc R U
C7 C 0.6956(3) 0.9301(4) 0.65780(7) 0.0281(7) Uani 1 1 d . .
C8 C 0.8787(3) 0.9942(3) 0.61551(7) 0.0249(6) Uani 1 1 d . .
C9 C 0.9722(3) 1.0506(4) 0.64034(7) 0.0305(7) Uani 1 1 d . .
H9 H 0.9466 1.0661 0.6638 0.037 Uiso 1 1 calc R U
C10 C 1.0996(3) 1.0833(4) 0.63095(7) 0.0331(7) Uani 1 1 d . .
H10 H 1.1599 1.1202 0.6481 0.040 Uiso 1 1 calc R U
C11 C 1.1414(3) 1.0628(4) 0.59640(8) 0.0343(7) Uani 1 1 d . .
H11 H 1.2296 1.0810 0.5902 0.041 Uiso 1 1 calc R U
C12 C 1.0503(3) 1.0152(3) 0.57152(7) 0.0256(6) Uani 1 1 d . .
H12 H 1.0777 1.0037 0.5481 0.031 Uiso 1 1 calc R U
C13 C 0.9184(3) 0.9830(3) 0.57966(6) 0.0229(6) Uani 1 1 d . .
C14 C 0.8254(3) 0.9443(3) 0.54984(7) 0.0236(6) Uani 1 1 d . .
C15 C 1.0718(3) 0.6037(3) 0.52532(6) 0.0253(6) Uani 1 1 d . .
H15A H 1.0036 0.6309 0.5426 0.030 Uiso 1 1 calc R U
H15B H 1.1539 0.6581 0.5332 0.030 Uiso 1 1 calc R U
N2 N 1.0340(2) 0.6781(3) 0.49051(6) 0.0243(5) Uani 1 1 d D .
H2A H 1.021(2) 0.7952(15) 0.4925(7) 0.029 Uiso 1 1 d D U
H2B H 1.102(2) 0.655(3) 0.4758(6) 0.029 Uiso 1 1 d D U
C16 C 0.9111(3) 0.5946(4) 0.47742(7) 0.0257(6) Uani 1 1 d . .
H16A H 0.8890 0.6433 0.4543 0.031 Uiso 1 1 calc R U
H16B H 0.8388 0.6216 0.4935 0.031 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
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
C8 N1 C7 129.4(2) . .
C8 N1 H1 113(2) . .
C7 N1 H1 117(2) . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C3 C2 C7 117.3(3) . .
C3 C2 C1 122.1(3) . .
C7 C2 C1 120.6(2) . .
C4 C3 C2 122.9(3) . .
C4 C3 Cl1 117.4(2) . .
C2 C3 Cl1 119.6(2) . .
C5 C4 C3 118.7(3) . .
C5 C4 H4 120.6 . .
C3 C4 H4 120.6 . .
C4 C5 C6 120.7(3) . .
C4 C5 H5 119.6 . .
C6 C5 H5 119.6 . .
C5 C6 C7 119.7(3) . .
C5 C6 H6 120.1 . .
C7 C6 H6 120.1 . .
C2 C7 C6 120.5(3) . .
C2 C7 N1 117.6(2) . .
C6 C7 N1 121.8(3) . .
N1 C8 C9 122.3(2) . .
N1 C8 C13 119.7(2) . .
C9 C8 C13 118.0(3) . .
C10 C9 C8 121.4(3) . .
C10 C9 H9 119.3 . .
C8 C9 H9 119.3 . .
C9 C10 C11 121.1(3) . .
C9 C10 H10 119.4 . .
C11 C10 H10 119.4 . .
C12 C11 C10 118.3(3) . .
C12 C11 H11 120.8 . .
C10 C11 H11 120.8 . .
C11 C12 C13 122.7(3) . .
C11 C12 H12 118.6 . .
C13 C12 H12 118.6 . .
C12 C13 C8 118.3(2) . .
C12 C13 C14 118.0(2) . .
C8 C13 C14 123.7(2) . .
O2 C14 O1 122.9(2) . .
O2 C14 C13 119.0(2) . .
O1 C14 C13 118.1(2) . .
N2 C15 C16 110.0(2) . 5_766
N2 C15 H15A 109.7 . .
C16 C15 H15A 109.7 5_766 .
N2 C15 H15B 109.7 . .
C16 C15 H15B 109.7 5_766 .
H15A C15 H15B 108.2 . .
C16 N2 C15 110.9(2) . .
C16 N2 H2A 108.8(18) . .
C15 N2 H2A 109.4(17) . .
C16 N2 H2B 110.7(18) . .
C15 N2 H2B 106.5(18) . .
H2A N2 H2B 110.6(15) . .
N2 C16 C15 110.1(2) . 5_766
N2 C16 H16A 109.6 . .
C15 C16 H16A 109.6 5_766 .
N2 C16 H16B 109.6 . .
C15 C16 H16B 109.6 5_766 .
H16A C16 H16B 108.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C3 1.767(3) .
O1 C14 1.293(3) .
O2 C14 1.268(3) .
N1 C8 1.388(4) .
N1 C7 1.421(4) .
N1 H1 0.892(10) .
C1 C2 1.523(4) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 C3 1.410(4) .
C2 C7 1.418(4) .
C3 C4 1.399(4) .
C4 C5 1.396(5) .
C4 H4 0.9500 .
C5 C6 1.404(4) .
C5 H5 0.9500 .
C6 C7 1.420(4) .
C6 H6 0.9500 .
C8 C9 1.423(4) .
C8 C13 1.443(4) .
C9 C10 1.384(4) .
C9 H9 0.9500 .
C10 C11 1.407(4) .
C10 H10 0.9500 .
C11 C12 1.389(4) .
C11 H11 0.9500 .
C12 C13 1.416(4) .
C12 H12 0.9500 .
C13 C14 1.525(4) .
C15 N2 1.507(3) .
C15 C16 1.525(4) 5_766
C15 H15A 0.9900 .
C15 H15B 0.9900 .
N2 C16 1.504(4) .
N2 H2A 0.905(10) .
N2 H2B 0.916(9) .
C16 C15 1.525(4) 5_766
C16 H16A 0.9900 .
C16 H16B 0.9900 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C7 C2 C3 C4 -0.6(5) . .
C1 C2 C3 C4 178.2(3) . .
C7 C2 C3 Cl1 179.6(2) . .
C1 C2 C3 Cl1 -1.5(4) . .
C2 C3 C4 C5 -0.2(5) . .
Cl1 C3 C4 C5 179.6(2) . .
C3 C4 C5 C6 0.6(5) . .
C4 C5 C6 C7 -0.1(5) . .
C3 C2 C7 C6 1.1(4) . .
C1 C2 C7 C6 -177.8(3) . .
C3 C2 C7 N1 177.6(3) . .
C1 C2 C7 N1 -1.3(4) . .
C5 C6 C7 C2 -0.8(4) . .
C5 C6 C7 N1 -177.1(3) . .
C8 N1 C7 C2 151.0(3) . .
C8 N1 C7 C6 -32.6(4) . .
C7 N1 C8 C9 -15.2(5) . .
C7 N1 C8 C13 167.7(3) . .
N1 C8 C9 C10 178.9(3) . .
C13 C8 C9 C10 -4.0(4) . .
C8 C9 C10 C11 0.3(5) . .
C9 C10 C11 C12 2.4(4) . .
C10 C11 C12 C13 -1.4(4) . .
C11 C12 C13 C8 -2.3(4) . .
C11 C12 C13 C14 175.7(3) . .
N1 C8 C13 C12 -177.9(2) . .
C9 C8 C13 C12 4.9(4) . .
N1 C8 C13 C14 4.2(4) . .
C9 C8 C13 C14 -173.0(2) . .
C12 C13 C14 O2 -5.1(4) . .
C8 C13 C14 O2 172.8(2) . .
C12 C13 C14 O1 175.6(2) . .
C8 C13 C14 O1 -6.5(4) . .
C16 C15 N2 C16 57.9(3) 5_766 .
C15 N2 C16 C15 -58.0(3) . 5_766
