#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/18/4501818.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_4501818
loop_
_publ_author_name
'Cheney, Miranda L.'
'Weyna, David R.'
'Shan, Ning'
'Hanna, Mazen'
'Wojtas, Lukasz'
'Zaworotko, Michael J.'
_publ_section_title
;
 Supramolecular Architectures of Meloxicam Carboxylic Acid Cocrystals, a
 Crystal Engineering Case Study
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4401
_journal_paper_doi               10.1021/cg100514g
_journal_volume                  10
_journal_year                    2010
_chemical_formula_sum            'C32 H30 N6 O12 S4'
_chemical_formula_weight         818.86
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                82.250(9)
_cell_angle_beta                 81.368(9)
_cell_angle_gamma                70.519(9)
_cell_formula_units_Z            1
_cell_length_a                   7.145(5)
_cell_length_b                   8.475(5)
_cell_length_c                   15.088(9)
_cell_measurement_reflns_used    843
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.441
_cell_measurement_theta_min      2.7425
_cell_volume                     848.0(9)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD'
_diffrn_measurement_method       'omega 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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4399
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_correction_T_min  0.9006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0650P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1162
_reflns_number_gt                2298
_reflns_number_total             3031
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg100514g_si_002.cif
_cod_data_source_block           5_t1x
_cod_original_cell_volume        848.1(9)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4501818
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.82544(11) 0.44443(9) 0.33573(5) 0.0230(2) Uani 1 1 d .
S2 S 0.25677(10) 0.96796(8) 0.03352(5) 0.0218(2) Uani 1 1 d .
C1 C 0.7910(4) 0.2111(3) 0.24071(19) 0.0194(6) Uani 1 1 d .
N1 N 0.6028(3) 0.5403(3) 0.30344(14) 0.0205(5) Uani 1 1 d .
O1 O 0.6669(3) 0.3194(2) 0.10138(13) 0.0261(5) Uani 1 1 d .
H1 H 0.5899 0.4034 0.0741 0.039 Uiso 1 1 calc R
C2 C 0.8253(4) 0.0476(3) 0.2210(2) 0.0242(7) Uani 1 1 d .
H2 H 0.7852 0.0279 0.1674 0.029 Uiso 1 1 calc R
N2 N 0.4269(3) 0.8049(3) 0.18664(16) 0.0198(5) Uani 1 1 d .
H2N H 0.469(4) 0.812(4) 0.240(2) 0.029(9) Uiso 1 1 d .
O2 O 0.9643(3) 0.5012(2) 0.27264(13) 0.0288(5) Uani 1 1 d .
C3 C 0.9183(4) -0.0866(4) 0.2798(2) 0.0282(7) Uani 1 1 d .
H3 H 0.9420 -0.1984 0.2662 0.034 Uiso 1 1 calc R
N3 N 0.3101(3) 1.0989(3) 0.16756(15) 0.0213(5) Uani 1 1 d .
O3 O 0.8166(3) 0.4593(2) 0.42917(13) 0.0328(5) Uani 1 1 d .
C4 C 0.9768(4) -0.0589(4) 0.3583(2) 0.0268(7) Uani 1 1 d .
H4 H 1.0374 -0.1516 0.3989 0.032 Uiso 1 1 calc R
O4 O 0.4400(3) 0.6338(2) 0.08073(13) 0.0253(5) Uani 1 1 d .
C5 C 0.9477(4) 0.1025(4) 0.37790(19) 0.0241(7) Uani 1 1 d .
H5 H 0.9882 0.1219 0.4315 0.029 Uiso 1 1 calc R
C6 C 0.8584(4) 0.2359(3) 0.31800(19) 0.0203(6) Uani 1 1 d .
C7 C 0.6756(4) 0.3556(3) 0.18429(18) 0.0205(6) Uani 1 1 d .
C8 C 0.5876(4) 0.5087(3) 0.21450(18) 0.0195(6) Uani 1 1 d .
C9 C 0.4301(4) 0.5357(4) 0.3706(2) 0.0284(7) Uani 1 1 d .
H9A H 0.3059 0.6048 0.3461 0.043 Uiso 1 1 calc R
H9B H 0.4408 0.5798 0.4257 0.043 Uiso 1 1 calc R
H9C H 0.4295 0.4195 0.3842 0.043 Uiso 1 1 calc R
C10 C 0.4788(4) 0.6511(3) 0.15548(19) 0.0206(6) Uani 1 1 d .
C11 C 0.3372(4) 0.9551(3) 0.13697(18) 0.0187(6) Uani 1 1 d .
C12 C 0.2221(4) 1.2288(3) 0.10627(19) 0.0229(7) Uani 1 1 d .
H12 H 0.1914 1.3430 0.1171 0.028 Uiso 1 1 calc R
C13 C 0.1817(4) 1.1854(3) 0.03000(18) 0.0203(6) Uani 1 1 d .
C14 C 0.0899(4) 1.2926(4) -0.04922(19) 0.0265(7) Uani 1 1 d .
H14A H -0.0508 1.2995 -0.0448 0.040 Uiso 1 1 calc R
H14B H 0.1611 1.2430 -0.1047 0.040 Uiso 1 1 calc R
H14C H 0.0992 1.4056 -0.0502 0.040 Uiso 1 1 calc R
C21 C 0.4317(4) 0.0288(4) 0.37974(19) 0.0227(7) Uani 1 1 d .
O21 O 0.4710(3) -0.1121(2) 0.35798(13) 0.0295(5) Uani 1 1 d .
C22 C 0.4560(4) 0.0616(4) 0.47100(18) 0.0230(6) Uani 1 1 d .
H22 H 0.4071 0.1735 0.4878 0.028 Uiso 1 1 calc R
O22 O 0.3642(3) 0.1668(2) 0.32698(12) 0.0249(5) Uani 1 1 d .
H22O H 0.3553 0.1417 0.2761 0.037 Uiso 1 1 calc R
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'
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
O3 S1 O2 120.12(13) .
O3 S1 N1 108.85(12) .
O2 S1 N1 107.18(12) .
O3 S1 C6 110.04(13) .
O2 S1 C6 108.01(12) .
N1 S1 C6 100.92(13) .
C11 S2 C13 89.25(13) .
C2 C1 C6 118.7(2) .
C2 C1 C7 120.9(3) .
C6 C1 C7 120.2(2) .
C8 N1 C9 115.1(2) .
C8 N1 S1 113.11(17) .
C9 N1 S1 116.53(18) .
C3 C2 C1 119.8(3) .
C10 N2 C11 123.9(3) .
C4 C3 C2 120.5(3) .
C11 N3 C12 109.8(2) .
C5 C4 C3 120.4(3) .
C4 C5 C6 118.8(3) .
C5 C6 C1 121.7(3) .
C5 C6 S1 121.6(2) .
C1 C6 S1 116.8(2) .
O1 C7 C8 124.1(2) .
O1 C7 C1 113.6(2) .
C8 C7 C1 122.2(3) .
C7 C8 N1 121.7(2) .
C7 C8 C10 120.8(3) .
N1 C8 C10 117.5(2) .
O4 C10 N2 121.7(2) .
O4 C10 C8 122.3(3) .
N2 C10 C8 115.9(3) .
N3 C11 N2 120.5(3) .
N3 C11 S2 115.3(2) .
N2 C11 S2 124.2(2) .
C13 C12 N3 116.6(3) .
C12 C13 C14 130.4(3) .
C12 C13 S2 108.9(2) .
C14 C13 S2 120.7(2) .
O21 C21 O22 124.6(3) .
O21 C21 C22 122.3(3) .
O22 C21 C22 113.1(2) .
C22 C22 C21 121.2(3) 2_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O3 1.423(2) .
S1 O2 1.426(2) .
S1 N1 1.640(2) .
S1 C6 1.756(3) .
S2 C11 1.720(3) .
S2 C13 1.735(3) .
C1 C2 1.389(4) .
C1 C6 1.392(4) .
C1 C7 1.470(4) .
N1 C8 1.430(3) .
N1 C9 1.482(4) .
O1 C7 1.343(3) .
C2 C3 1.387(4) .
N2 C10 1.359(4) .
N2 C11 1.391(3) .
C3 C4 1.387(4) .
N3 C11 1.305(3) .
N3 C12 1.379(3) .
C4 C5 1.379(4) .
O4 C10 1.240(3) .
C5 C6 1.385(4) .
C7 C8 1.347(4) .
C8 C10 1.465(4) .
C12 C13 1.352(4) .
C13 C14 1.493(4) .
C21 O21 1.212(3) .
C21 O22 1.312(3) .
C21 C22 1.487(4) .
C22 C22 1.316(5) 2_656
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 O4 0.84 1.90 2.621(3) 143.7 .
O1 H1 O4 0.84 2.45 2.902(3) 114.7 2_665
N2 H2N O21 0.91(3) 1.98(3) 2.857(4) 161(3) 1_565
O22 H22O N3 0.84 1.82 2.658(3) 174.4 1_545
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144774
