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#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/62/7216213.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_7216213
loop_
_publ_author_name
'Thomas, Lynne H.'
'Klapwijk, Anneke R.'
'Wales, Craig'
'Wilson, Chick C.'
_publ_section_title
;
 Intermolecular hydrogen transfer and solubility tuning in multi-component
 molecular crystals of the API piroxicam
;
_journal_issue                   26
_journal_name_full               CrystEngComm
_journal_page_first              5924
_journal_paper_doi               10.1039/c4ce00246f
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C15 H14 N3 O4 S, C6 H Cl2 O4'
_chemical_formula_sum            'C21 H15 Cl2 N3 O8 S'
_chemical_formula_weight         540.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.925(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5627(5)
_cell_length_b                   13.3395(7)
_cell_length_c                   19.3963(12)
_cell_measurement_reflns_used    39751
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      89.897
_cell_measurement_theta_min      1
_cell_volume                     2175.3(2)
_computing_cell_refinement       'Bruker APEX2 (2009)'
_computing_data_collection       'Bruker APEX2 (2009)'
_computing_data_reduction        'Bruker APEX2 (2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'CCD; rotation images'
_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  0.0920
_diffrn_reflns_av_sigmaI/netI    0.0796
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            38649
_diffrn_reflns_theta_full        27.72
_diffrn_reflns_theta_max         27.72
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.452
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.9023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Blessing, 1997)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             1104
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         5083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.922
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0289P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0678
_refine_ls_wR_factor_ref         0.0762
_reflns_number_gt                3284
_reflns_number_total             5083
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00246f2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 7216204--7216215.cif.'
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7216213
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
H12 H -0.140(2) 0.5362(15) 0.3403(11) 0.019(6) Uiso 1 1 d
H11 H -0.047(2) 0.6935(15) 0.3780(12) 0.019(6) Uiso 1 1 d
H4 H 0.534(2) 0.7098(15) -0.1471(11) 0.017(6) Uiso 1 1 d
H7 H 0.009(3) 0.7433(15) 0.0196(12) 0.026(6) Uiso 1 1 d
H9 H -0.072(3) 0.7526(16) 0.0909(12) 0.031(7) Uiso 1 1 d
H13 H -0.091(2) 0.4724(15) 0.2374(11) 0.017(6) Uiso 1 1 d
H2 H 0.302(3) 0.4407(15) -0.0642(11) 0.022(7) Uiso 1 1 d
H10 H 0.107(2) 0.7824(15) 0.3129(11) 0.014(6) Uiso 1 1 d
H5 H 0.400(3) 0.7289(17) -0.0590(12) 0.033(7) Uiso 1 1 d
H3 H 0.564(2) 0.5520(15) -0.1979(11) 0.020(6) Uiso 1 1 d
H1 H 0.438(2) 0.4159(15) -0.1557(10) 0.018(6) Uiso 1 1 d
H8 H 0.052(3) 0.8324(16) 0.0718(11) 0.023(7) Uiso 1 1 d
H14 H 0.095(3) 0.4317(18) 0.0986(14) 0.054(9) Uiso 1 1 d
H6 H 0.281(3) 0.6753(17) 0.0178(13) 0.037(8) Uiso 1 1 d
H15 H 0.405(3) 0.5812(18) 0.2980(14) 0.043(9) Uiso 1 1 d
S1 S 0.22971(7) 0.74010(4) 0.18995(3) 0.01620(13) Uani 1 1 d
Cl2 Cl 0.80123(7) 0.53699(4) 0.50984(3) 0.02354(15) Uani 1 1 d
Cl3 Cl 0.25249(7) 0.31402(4) 0.29987(3) 0.02535(15) Uani 1 1 d
O8 O 0.17273(18) 0.45919(11) 0.02896(8) 0.0210(4) Uani 1 1 d
O2 O 0.44676(18) 0.23702(11) 0.43408(8) 0.0226(4) Uani 1 1 d
O4 O 0.36089(19) 0.52545(12) 0.29357(8) 0.0228(4) Uani 1 1 d
O1 O 0.68962(18) 0.32443(10) 0.51973(8) 0.0214(4) Uani 1 1 d
O3 O 0.58158(18) 0.61655(11) 0.38131(8) 0.0245(4) Uani 1 1 d
O6 O 0.38358(17) 0.69509(10) 0.21108(7) 0.0184(3) Uani 1 1 d
O7 O 0.05524(19) 0.44384(11) 0.14042(9) 0.0222(4) Uani 1 1 d
N1 N 0.1603(2) 0.70533(12) 0.10841(9) 0.0165(4) Uani 1 1 d
O5 O 0.21624(18) 0.84673(10) 0.19419(8) 0.0203(4) Uani 1 1 d
N2 N 0.2640(2) 0.61258(14) 0.00065(9) 0.0181(4) Uani 1 1 d
C5 C 0.4803(3) 0.32250(16) 0.41948(11) 0.0171(5) Uani 1 1 d
N3 N 0.4097(2) 0.66434(14) -0.08028(10) 0.0189(4) Uani 1 1 d
C6 C 0.6170(3) 0.37566(16) 0.46899(11) 0.0170(5) Uani 1 1 d
C13 C 0.1411(3) 0.59804(15) 0.10072(11) 0.0160(5) Uani 1 1 d
C4 C 0.6500(3) 0.47457(15) 0.45455(11) 0.0162(5) Uani 1 1 d
C16 C 0.1918(3) 0.55017(16) 0.04111(12) 0.0184(5) Uani 1 1 d
C17 C 0.3386(3) 0.58622(16) -0.05372(11) 0.0173(5) Uani 1 1 d
C3 C 0.5627(3) 0.52769(16) 0.39706(12) 0.0180(5) Uani 1 1 d
C22 C 0.0668(3) 0.72143(17) 0.29789(12) 0.0196(5) Uani 1 1 d
C1 C 0.3982(3) 0.37582(16) 0.35784(11) 0.0176(5) Uani 1 1 d
C14 C 0.0796(3) 0.54301(16) 0.14834(11) 0.0169(5) Uani 1 1 d
C15 C 0.0235(3) 0.76449(19) 0.06995(13) 0.0220(5) Uani 1 1 d
C10 C 0.0399(3) 0.58591(15) 0.21247(11) 0.0169(5) Uani 1 1 d
C2 C 0.4349(3) 0.47176(16) 0.34804(11) 0.0173(5) Uani 1 1 d
C19 C 0.4304(3) 0.48016(17) -0.13593(12) 0.0202(5) Uani 1 1 d
C11 C 0.0989(2) 0.68049(15) 0.23664(11) 0.0154(5) Uani 1 1 d
C18 C 0.3486(3) 0.49158(17) -0.08215(12) 0.0190(5) Uani 1 1 d
C20 C 0.5028(3) 0.56153(17) -0.16175(12) 0.0217(5) Uani 1 1 d
C21 C 0.4904(3) 0.65351(18) -0.13250(12) 0.0226(6) Uani 1 1 d
C9 C -0.0501(3) 0.53341(17) 0.25283(12) 0.0203(5) Uani 1 1 d
C8 C -0.0806(3) 0.57372(18) 0.31421(13) 0.0232(6) Uani 1 1 d
C7 C -0.0234(3) 0.66742(17) 0.33683(12) 0.0235(6) Uani 1 1 d
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'
S S 0.1246 0.1234 '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
O5 S1 O6 118.63(9)
O5 S1 N1 108.47(9)
O6 S1 N1 107.53(9)
O5 S1 C11 110.72(9)
O6 S1 C11 107.68(9)
N1 S1 C11 102.58(10)
C2 O4 H15 105.2(19)
C14 O7 H14 101.0(15)
C13 N1 C15 114.20(18)
C13 N1 S1 113.02(14)
C15 N1 S1 115.98(14)
C16 N2 C17 127.49(19)
C16 N2 H6 114.3(15)
C17 N2 H6 117.0(15)
O2 C5 C1 123.3(2)
O2 C5 C6 118.00(19)
C1 C5 C6 118.68(18)
C21 N3 C17 122.5(2)
C21 N3 H5 121.1(14)
C17 N3 H5 116.3(14)
O1 C6 C4 125.7(2)
O1 C6 C5 116.20(18)
C4 C6 C5 118.1(2)
C14 C13 N1 120.99(19)
C14 C13 C16 120.91(19)
N1 C13 C16 118.10(18)
C6 C4 C3 122.6(2)
C6 C4 Cl2 119.29(17)
C3 C4 Cl2 118.07(16)
O8 C16 N2 122.9(2)
O8 C16 C13 122.1(2)
N2 C16 C13 115.03(19)
N3 C17 N2 113.64(19)
N3 C17 C18 118.9(2)
N2 C17 C18 127.5(2)
O3 C3 C4 126.9(2)
O3 C3 C2 115.5(2)
C4 C3 C2 117.62(19)
C7 C22 C11 119.1(2)
C7 C22 H10 120.6(13)
C11 C22 H10 120.3(13)
C2 C1 C5 119.6(2)
C2 C1 Cl3 121.64(18)
C5 C1 Cl3 118.71(16)
O7 C14 C13 121.7(2)
O7 C14 C10 115.17(19)
C13 C14 C10 123.1(2)
N1 C15 H7 106.1(12)
N1 C15 H9 110.1(13)
H7 C15 H9 113.3(18)
N1 C15 H8 108.8(14)
H7 C15 H8 107.0(18)
H9 C15 H8 111.4(18)
C9 C10 C11 117.9(2)
C9 C10 C14 121.6(2)
C11 C10 C14 120.43(19)
O4 C2 C1 122.5(2)
O4 C2 C3 114.45(19)
C1 C2 C3 123.1(2)
C18 C19 C20 121.0(2)
C18 C19 H1 119.8(12)
C20 C19 H1 119.2(12)
C22 C11 C10 121.6(2)
C22 C11 S1 120.94(17)
C10 C11 S1 117.25(16)
C19 C18 C17 118.8(2)
C19 C18 H2 123.0(14)
C17 C18 H2 118.2(14)
C21 C20 C19 118.5(2)
C21 C20 H3 121.2(12)
C19 C20 H3 120.2(12)
N3 C21 C20 120.3(2)
N3 C21 H4 116.6(13)
C20 C21 H4 123.1(13)
C8 C9 C10 120.5(2)
C8 C9 H13 120.6(13)
C10 C9 H13 118.8(13)
C9 C8 C7 120.9(2)
C9 C8 H12 118.3(13)
C7 C8 H12 120.8(13)
C22 C7 C8 119.9(2)
C22 C7 H11 120.7(13)
C8 C7 H11 119.4(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O5 1.4306(14)
S1 O6 1.4352(15)
S1 N1 1.6473(18)
S1 C11 1.758(2)
Cl2 C4 1.730(2)
Cl3 C1 1.723(2)
O8 C16 1.241(2)
O2 C5 1.222(2)
O4 C2 1.333(3)
O4 H15 0.83(2)
O1 C6 1.261(2)
O3 C3 1.242(2)
O7 C14 1.343(2)
O7 H14 0.95(3)
N1 C13 1.445(2)
N1 C15 1.490(3)
N2 C16 1.369(3)
N2 C17 1.378(3)
N2 H6 0.90(2)
C5 C1 1.453(3)
C5 C6 1.539(3)
N3 C21 1.338(3)
N3 C17 1.357(3)
N3 H5 0.96(2)
C6 C4 1.389(3)
C13 C14 1.362(3)
C13 C16 1.457(3)
C4 C3 1.410(3)
C17 C18 1.387(3)
C3 C2 1.505(3)
C22 C7 1.381(3)
C22 C11 1.382(3)
C22 H10 0.91(2)
C1 C2 1.340(3)
C14 C10 1.466(3)
C15 H7 1.00(2)
C15 H9 1.00(2)
C15 H8 0.94(2)
C10 C9 1.387(3)
C10 C11 1.406(3)
C19 C18 1.371(3)
C19 C20 1.390(3)
C19 H1 0.95(2)
C18 H2 0.89(2)
C20 C21 1.364(3)
C20 H3 0.96(2)
C21 H4 0.91(2)
C9 C8 1.376(3)
C9 H13 0.913(19)
C8 C7 1.383(3)
C8 H12 0.93(2)
C7 H11 0.93(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H5 O1 0.96(2) 1.74(2) 2.654(2) 157(2) 2_655
N3 H5 O2 0.96(2) 2.53(2) 3.028(2) 112.2(16) 2_655
N2 H6 O1 0.90(2) 2.15(2) 2.891(2) 139(2) 2_655
N2 H6 O2 0.90(2) 2.48(2) 3.050(2) 121.4(18) 2_655
O4 H15 O6 0.83(2) 2.25(3) 2.799(2) 124(2) .
O7 H14 O8 0.95(3) 1.65(3) 2.560(2) 157(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139198640
