#------------------------------------------------------------------------------
#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/70/7207068.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_7207068
loop_
_publ_author_name
'Tumanov, Nikolay A.'
'Myz, Svetlana A.'
'Shakhtshneider, Tatyana P.'
'Boldyreva, Elena V.'
_publ_section_title
;
 Are meloxicam dimers really the structure-forming units in the
 ‘meloxicam--carboxylic acid’ co-crystals family? Relation
 between crystal structures and dissolution behaviour
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              305
_journal_paper_doi               10.1039/c1ce05902e
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C14 H13 N3 O4 S2, 0.5(C8 H6 O4)'
_chemical_formula_sum            'C18 H16 N3 O6 S2'
_chemical_formula_weight         434.46
_chemical_name_common
;
4-Hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-2H-1,2-
benzothiazine-3-carboxamide 1,1-dioxide terephtalic acid
;
_chemical_name_systematic
;
4-Hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-2H-1,2-benzothiazine-3-
carboxamide 1,1-dioxide terephtalic acid
;
_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                91.355(5)
_cell_angle_beta                 107.856(6)
_cell_angle_gamma                109.444(6)
_cell_formula_units_Z            2
_cell_length_a                   8.5979(6)
_cell_length_b                   10.4551(6)
_cell_length_c                   11.7515(7)
_cell_measurement_reflns_used    4132
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.7462
_cell_measurement_theta_min      3.6043
_cell_volume                     938.79(12)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material
;
publCIF (Westrip., 2008),
enCIFer (Allen et al., 2004).
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3457
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Gemini Ultra R CCD'
_diffrn_measurement_method       ω
_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  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0703
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17934
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         3.61
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             450
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.876
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5721
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.876
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0432
_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)+(0.0422P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0954
_reflns_number_gt                3365
_reflns_number_total             5721
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c1ce05902e.txt
_cod_data_source_block           mel_tereph
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_iucr_refine_instruction_details' was replaced with
'_iucr_refine_instructions_details' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_database_code               7207068
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
S1 S 0.81131(6) 0.76219(4) 0.22622(4) 0.03637(13) Uani 1 1 d
S2 S 0.96719(6) 0.18694(4) 0.16582(5) 0.03994(14) Uani 1 1 d
C1 C 0.5649(4) 0.8824(2) 0.2378(2) 0.0478(6) Uani 1 1 d
H1A H 0.641(3) 0.966(2) 0.271(2) 0.064(7) Uiso 1 1 d
H1B H 0.472(3) 0.873(2) 0.2692(19) 0.060(6) Uiso 1 1 d
H1C H 0.523(3) 0.882(2) 0.147(2) 0.081(8) Uiso 1 1 d
C2 C 0.6404(2) 0.77255(18) 0.26999(16) 0.0347(4) Uani 1 1 d
C3 C 0.5851(2) 0.66564(18) 0.32675(17) 0.0347(4) Uani 1 1 d
H3 H 0.492(2) 0.6476(18) 0.3614(16) 0.039(5) Uiso 1 1 d
C4 C 0.7885(2) 0.61013(16) 0.28437(15) 0.0287(4) Uani 1 1 d
C5 C 0.9993(2) 0.55519(17) 0.21426(16) 0.0310(4) Uani 1 1 d
C6 C 1.0698(2) 0.44900(16) 0.20028(15) 0.0288(4) Uani 1 1 d
C7 C 1.1760(2) 0.46125(16) 0.13309(15) 0.0292(4) Uani 1 1 d
C8 C 1.2451(2) 0.35395(17) 0.11564(15) 0.0302(4) Uani 1 1 d
C9 C 1.3991(2) 0.3839(2) 0.08918(16) 0.0369(4) Uani 1 1 d
H9 H 1.460(2) 0.4785(18) 0.0844(15) 0.034(5) Uiso 1 1 d
C10 C 1.4657(3) 0.2823(2) 0.07817(18) 0.0441(5) Uani 1 1 d
H10 H 1.572(3) 0.310(2) 0.0610(18) 0.051(6) Uiso 1 1 d
C11 C 1.3786(3) 0.1498(2) 0.09144(19) 0.0477(5) Uani 1 1 d
H11 H 1.421(2) 0.077(2) 0.0809(18) 0.051(6) Uiso 1 1 d
C12 C 1.2251(3) 0.1167(2) 0.11781(19) 0.0437(5) Uani 1 1 d
H12 H 1.164(2) 0.0283(19) 0.1288(16) 0.041(5) Uiso 1 1 d
C13 C 1.1589(2) 0.21900(18) 0.12959(16) 0.0344(4) Uani 1 1 d
C14 C 1.1271(3) 0.3386(3) 0.3829(2) 0.0430(5) Uani 1 1 d
H14A H 1.129(2) 0.420(2) 0.4269(18) 0.047(6) Uiso 1 1 d
H14B H 1.081(3) 0.262(2) 0.4131(17) 0.050(6) Uiso 1 1 d
H14C H 1.248(3) 0.348(2) 0.3881(19) 0.070(7) Uiso 1 1 d
O1 O 1.22477(17) 0.56963(13) 0.07617(12) 0.0386(3) Uani 1 1 d
H1 H 1.177(3) 0.623(2) 0.1001(19) 0.055(7) Uiso 1 1 d
O2 O 1.04166(17) 0.66384(12) 0.17179(12) 0.0419(3) Uani 1 1 d
O3 O 0.82635(17) 0.18189(13) 0.05993(13) 0.0528(4) Uani 1 1 d
O4 O 0.94778(19) 0.07662(13) 0.23485(15) 0.0598(4) Uani 1 1 d
O5 O 0.78591(19) 0.30891(15) 0.42518(17) 0.0697(5) Uani 1 1 d
O6 O 0.53431(18) 0.33394(14) 0.40547(14) 0.0479(4) Uani 1 1 d
H6 H 0.581(3) 0.408(3) 0.381(3) 0.098(10) Uiso 1 1 d
N1 N 0.66860(19) 0.57164(14) 0.33517(13) 0.0320(3) Uani 1 1 d
N2 N 0.88283(19) 0.52820(15) 0.27463(14) 0.0323(3) Uani 1 1 d
H2 H 0.859(3) 0.456(2) 0.3048(17) 0.046(6) Uiso 1 1 d
N3 N 1.01715(18) 0.32803(14) 0.25546(13) 0.0317(3) Uani 1 1 d
C15 C 0.6402(2) 0.26546(18) 0.43081(17) 0.0375(4) Uani 1 1 d
C16 C 0.5656(2) 0.12891(17) 0.46756(16) 0.0321(4) Uani 1 1 d
C17 C 0.3870(3) 0.06351(19) 0.44119(18) 0.0384(5) Uani 1 1 d
H17 H 0.312(2) 0.1036(18) 0.4010(17) 0.042(5) Uiso 1 1 d
C18 C 0.6785(3) 0.06450(19) 0.52669(19) 0.0393(5) Uani 1 1 d
H18 H 0.798(3) 0.108(2) 0.5469(17) 0.050(6) Uiso 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'
S S 0.1246 0.1234 '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'
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
C4 S1 C2 88.97(8) .
O4 S2 O3 119.80(9) .
O4 S2 N3 108.10(8) .
O3 S2 N3 107.51(8) .
O4 S2 C13 108.86(8) .
O3 S2 C13 109.53(9) .
N3 S2 C13 101.47(8) .
C2 C1 H1A 112.8(15) .
C2 C1 H1B 111.1(12) .
H1A C1 H1B 103.5(19) .
C2 C1 H1C 110.9(13) .
H1A C1 H1C 107.7(19) .
H1B C1 H1C 110.5(19) .
C3 C2 C1 127.98(17) .
C3 C2 S1 109.60(12) .
C1 C2 S1 122.28(14) .
C2 C3 N1 116.20(16) .
C2 C3 H3 126.3(10) .
N1 C3 H3 117.5(10) .
N1 C4 N2 120.63(14) .
N1 C4 S1 115.37(12) .
N2 C4 S1 123.93(12) .
O2 C5 N2 121.59(15) .
O2 C5 C6 121.76(15) .
N2 C5 C6 116.65(14) .
C7 C6 N3 120.87(14) .
C7 C6 C5 121.17(14) .
N3 C6 C5 117.90(14) .
O1 C7 C6 123.55(15) .
O1 C7 C8 114.45(14) .
C6 C7 C8 122.00(14) .
C9 C8 C13 118.44(16) .
C9 C8 C7 121.43(16) .
C13 C8 C7 120.10(14) .
C10 C9 C8 120.44(18) .
C10 C9 H9 122.1(10) .
C8 C9 H9 117.3(10) .
C11 C10 C9 120.36(19) .
C11 C10 H10 123.3(12) .
C9 C10 H10 116.4(12) .
C10 C11 C12 120.60(19) .
C10 C11 H11 121.2(11) .
C12 C11 H11 118.2(11) .
C11 C12 C13 119.00(19) .
C11 C12 H12 122.6(11) .
C13 C12 H12 118.4(11) .
C12 C13 C8 121.16(17) .
C12 C13 S2 122.11(14) .
C8 C13 S2 116.71(12) .
N3 C14 H14A 107.1(11) .
N3 C14 H14B 109.3(13) .
H14A C14 H14B 111.3(17) .
N3 C14 H14C 110.5(13) .
H14A C14 H14C 109.9(18) .
H14B C14 H14C 108.7(17) .
C7 O1 H1 101.1(13) .
C15 O6 H6 110.0(18) .
C4 N1 C3 109.82(13) .
C5 N2 C4 124.27(14) .
C5 N2 H2 119.9(13) .
C4 N2 H2 115.7(13) .
C6 N3 C14 114.41(16) .
C6 N3 S2 112.54(11) .
C14 N3 S2 117.05(12) .
O5 C15 O6 122.92(16) .
O5 C15 C16 122.79(16) .
O6 C15 C16 114.30(15) .
C17 C16 C18 119.39(15) .
C17 C16 C15 121.83(15) .
C18 C16 C15 118.75(16) .
C18 C17 C16 120.53(16) 2_656
C18 C17 H17 119.2(12) 2_656
C16 C17 H17 120.3(12) .
C17 C18 C16 120.08(17) 2_656
C17 C18 H18 119.7(11) 2_656
C16 C18 H18 120.2(11) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C4 1.7201(15) .
S1 C2 1.7323(18) .
S2 O4 1.4197(13) .
S2 O3 1.4310(14) .
S2 N3 1.6423(15) .
S2 C13 1.7546(18) .
C1 C2 1.500(2) .
C1 H1A 0.89(2) .
C1 H1B 0.96(2) .
C1 H1C 1.02(2) .
C2 C3 1.340(2) .
C3 N1 1.386(2) .
C3 H3 0.975(18) .
C4 N1 1.3012(19) .
C4 N2 1.386(2) .
C5 O2 1.2388(18) .
C5 N2 1.358(2) .
C5 C6 1.458(2) .
C6 C7 1.357(2) .
C6 N3 1.4362(19) .
C7 O1 1.3412(18) .
C7 C8 1.470(2) .
C8 C9 1.389(2) .
C8 C13 1.399(2) .
C9 C10 1.385(3) .
C9 H9 0.965(16) .
C10 C11 1.377(3) .
C10 H10 0.95(2) .
C11 C12 1.381(3) .
C11 H11 0.97(2) .
C12 C13 1.391(2) .
C12 H12 0.932(18) .
C14 N3 1.484(3) .
C14 H14A 0.98(2) .
C14 H14B 0.90(2) .
C14 H14C 0.99(2) .
O1 H1 0.88(2) .
O5 C15 1.206(2) .
O6 C15 1.307(2) .
O6 H6 0.84(3) .
N2 H2 0.833(18) .
C15 C16 1.492(2) .
C16 C17 1.386(2) .
C16 C18 1.386(2) .
C17 C18 1.380(2) 2_656
C17 H17 0.907(18) .
C18 C17 1.380(2) 2_656
C18 H18 0.92(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
O1 H1 O2 0.88(2) 1.78(2) 2.6031(17) 155.4(18)
N2 H2 O5 0.833(18) 2.183(19) 2.9841(19) 161.4(18)
N2 H2 N3 0.833(18) 2.369(19) 2.7405(19) 107.8(15)
O6 H6 N1 0.84(3) 1.80(3) 2.6388(18) 175(3)
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_4
C4 S1 C2 C3 1.88(15) .
C4 S1 C2 C1 -174.15(19) .
C1 C2 C3 N1 174.0(2) .
S1 C2 C3 N1 -1.7(2) .
C2 S1 C4 N1 -1.81(15) .
C2 S1 C4 N2 175.24(16) .
O2 C5 C6 C7 -4.4(3) .
N2 C5 C6 C7 174.59(16) .
O2 C5 C6 N3 178.27(16) .
N2 C5 C6 N3 -2.7(2) .
N3 C6 C7 O1 177.72(15) .
C5 C6 C7 O1 0.5(3) .
N3 C6 C7 C8 -1.4(3) .
C5 C6 C7 C8 -178.59(16) .
O1 C7 C8 C9 25.8(2) .
C6 C7 C8 C9 -154.99(17) .
O1 C7 C8 C13 -156.34(16) .
C6 C7 C8 C13 22.8(3) .
C13 C8 C9 C10 -0.6(3) .
C7 C8 C9 C10 177.25(17) .
C8 C9 C10 C11 1.0(3) .
C9 C10 C11 C12 -1.1(3) .
C10 C11 C12 C13 0.6(3) .
C11 C12 C13 C8 -0.2(3) .
C11 C12 C13 S2 -178.74(16) .
C9 C8 C13 C12 0.2(3) .
C7 C8 C13 C12 -177.67(17) .
C9 C8 C13 S2 178.81(14) .
C7 C8 C13 S2 0.9(2) .
O4 S2 C13 C12 28.4(2) .
O3 S2 C13 C12 -104.37(17) .
N3 S2 C13 C12 142.20(16) .
O4 S2 C13 C8 -150.22(14) .
O3 S2 C13 C8 77.06(16) .
N3 S2 C13 C8 -36.37(15) .
N2 C4 N1 C3 -175.98(16) .
S1 C4 N1 C3 1.2(2) .
C2 C3 N1 C4 0.4(2) .
O2 C5 N2 C4 6.7(3) .
C6 C5 N2 C4 -172.38(16) .
N1 C4 N2 C5 174.25(17) .
S1 C4 N2 C5 -2.7(3) .
C7 C6 N3 C14 95.3(2) .
C5 C6 N3 C14 -87.44(19) .
C7 C6 N3 S2 -41.6(2) .
C5 C6 N3 S2 135.74(14) .
O4 S2 N3 C6 169.72(11) .
O3 S2 N3 C6 -59.64(13) .
C13 S2 N3 C6 55.30(12) .
O4 S2 N3 C14 34.13(15) .
O3 S2 N3 C14 164.77(13) .
C13 S2 N3 C14 -80.29(14) .
O5 C15 C16 C17 -161.1(2) .
O6 C15 C16 C17 19.0(3) .
O5 C15 C16 C18 17.0(3) .
O6 C15 C16 C18 -162.87(18) .
C18 C16 C17 C18 0.0(3) 2_656
C15 C16 C17 C18 178.14(18) 2_656
C17 C16 C18 C17 0.0(3) 2_656
C15 C16 C18 C17 -178.20(18) 2_656
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139196157
