#------------------------------------------------------------------------------
#$Date: 2025-08-21 04:34:05 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301843 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/05/4510592.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_4510592
loop_
_publ_author_name
'Suresh, Kuthuru'
'Nangia, Ashwini'
_publ_section_title
;
 Lornoxicam Salts: Crystal Structures, Conformations, and Solubility
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2945
_journal_paper_doi               10.1021/cg500231z
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C14 H14 N3 O7 S3 Cl'
_chemical_formula_sum            'C14 H14 Cl N3 O7 S3'
_chemical_formula_weight         467.91
_chemical_melting_point          479
_chemical_name_common            'Lornoxicam Mesylate salt'
_chemical_name_systematic
; 
 (3E)-6-chloro-3-[hydroxy(pyridin-2-ylamino)methylene]- 
2-methyl-2,3-dihydro-4H-thieno[2,3-e][1,2] thiazin-4-ol-1,1-dioxide) Mesylate  
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.707(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4730(11)
_cell_length_b                   13.2684(8)
_cell_length_c                   11.2407(8)
_cell_measurement_reflns_used    2465
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.3132
_cell_measurement_theta_min      2.9606
_cell_volume                     1867.0(3)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 16.3291
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_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  0.0575
_diffrn_reflns_av_sigmaI/netI    0.1203
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8057
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_T_max  0.9331
_exptl_absorpt_correction_T_min  0.8170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.907
_refine_ls_R_factor_all          0.1120
_refine_ls_R_factor_gt           0.0507
_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)+(0.0049P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0828
_reflns_number_gt                2030
_reflns_number_total             3818
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg500231z_si_005.cif
_cod_data_source_block           LXM-MSA
_cod_depositor_comments
'Adding full bibliography for 4510592--4510596.cif.'
_cod_original_cell_volume        1867.0(2)
_cod_database_code               4510592
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
_atom_site_refinement_flags
S3 S 0.56585(8) 0.82733(8) 0.06677(8) 0.0363(3) Uani 1 1 d .
S1 S 0.92170(9) 0.81662(8) 0.35735(9) 0.0454(3) Uani 1 1 d .
S2 S 1.18277(9) 0.65055(9) 0.60240(9) 0.0497(3) Uani 1 1 d .
Cl22 Cl 1.28330(9) 0.79955(9) 0.80748(8) 0.0610(4) Uani 1 1 d .
O7 O 0.6191(2) 0.7514(2) 0.1642(2) 0.0459(7) Uani 1 1 d .
O3 O 1.0663(2) 0.5296(2) 0.3620(2) 0.0561(8) Uani 1 1 d .
H3A H 1.0270 0.4914 0.3074 0.084 Uiso 1 1 calc R
N1 N 0.5947(2) 0.5945(2) -0.0636(2) 0.0358(8) Uani 1 1 d .
H1 H 0.5939 0.6586 -0.0529 0.043 Uiso 1 1 calc R
O5 O 0.5600(2) 0.7926(2) -0.0600(2) 0.0461(8) Uani 1 1 d .
N2 N 0.7456(2) 0.5943(2) 0.1212(2) 0.0335(8) Uani 1 1 d .
H2A H 0.7242 0.6506 0.1409 0.040 Uiso 1 1 calc R
O2 O 0.9459(2) 0.8363(2) 0.2465(2) 0.0578(9) Uani 1 1 d .
N3 N 0.8519(2) 0.7117(2) 0.3284(2) 0.0331(8) Uani 1 1 d .
O4 O 0.8880(2) 0.4865(2) 0.1686(2) 0.0496(8) Uani 1 1 d .
O6 O 0.4632(2) 0.8583(2) 0.0672(2) 0.0479(7) Uani 1 1 d .
C8 C 1.0096(3) 0.6093(3) 0.3751(3) 0.0360(10) Uani 1 1 d .
C6 C 0.8475(3) 0.5635(3) 0.1922(3) 0.0332(9) Uani 1 1 d .
C1 C 0.6749(3) 0.5401(3) 0.0196(3) 0.0310(9) Uani 1 1 d .
C7 C 0.9063(3) 0.6274(3) 0.3002(3) 0.0310(9) Uani 1 1 d .
C5 C 0.5156(3) 0.5519(3) -0.1634(3) 0.0451(11) Uani 1 1 d .
H5 H 0.4607 0.5917 -0.2178 0.054 Uiso 1 1 calc R
C9 C 1.0690(3) 0.6799(3) 0.4751(3) 0.0363(10) Uani 1 1 d .
C12 C 1.1846(3) 0.7691(3) 0.6652(3) 0.0420(11) Uani 1 1 d .
C2 C 0.6779(3) 0.4374(3) -0.0003(3) 0.0390(10) Uani 1 1 d .
H2 H 0.7335 0.3983 0.0540 0.047 Uiso 1 1 calc R
C11 C 1.1039(3) 0.8294(3) 0.5913(3) 0.0435(11) Uani 1 1 d .
H11 H 1.0938 0.8960 0.6097 0.052 Uiso 1 1 calc R
C13 C 0.7942(3) 0.6889(3) 0.4154(3) 0.0560(13) Uani 1 1 d .
H13A H 0.7577 0.7483 0.4262 0.084 Uiso 1 1 calc R
H13B H 0.8444 0.6675 0.4970 0.084 Uiso 1 1 calc R
H13C H 0.7432 0.6362 0.3789 0.084 Uiso 1 1 calc R
O1 O 0.8682(2) 0.8907(2) 0.4042(2) 0.0738(10) Uani 1 1 d .
C10 C 1.0377(3) 0.7757(3) 0.4824(3) 0.0374(10) Uani 1 1 d .
C4 C 0.5162(3) 0.4511(4) -0.1841(4) 0.0498(12) Uani 1 1 d .
H4 H 0.4625 0.4213 -0.2530 0.060 Uiso 1 1 calc R
C3 C 0.5973(3) 0.3942(3) -0.1018(4) 0.0469(11) Uani 1 1 d .
H3 H 0.5980 0.3250 -0.1147 0.056 Uiso 1 1 calc R
C14 C 0.6501(3) 0.9336(3) 0.1030(3) 0.0541(12) Uani 1 1 d .
H14A H 0.7184 0.9153 0.1010 0.081 Uiso 1 1 calc R
H14B H 0.6591 0.9579 0.1868 0.081 Uiso 1 1 calc R
H14C H 0.6187 0.9855 0.0410 0.081 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'
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
O6 S3 O7 113.38(15)
O6 S3 O5 112.59(16)
O7 S3 O5 110.15(15)
O6 S3 C14 107.93(18)
O7 S3 C14 106.42(18)
O5 S3 C14 105.87(16)
O2 S1 O1 120.41(19)
O2 S1 N3 106.37(15)
O1 S1 N3 109.00(18)
O2 S1 C10 109.44(18)
O1 S1 C10 109.74(17)
N3 S1 C10 99.87(17)
C9 S2 C12 90.43(19)
C8 O3 H3A 109.5
C1 N1 C5 122.4(3)
C1 N1 H1 118.8
C5 N1 H1 118.8
C6 N2 C1 124.1(3)
C6 N2 H2A 118.0
C1 N2 H2A 118.0
C7 N3 C13 114.9(3)
C7 N3 S1 113.7(2)
C13 N3 S1 116.2(2)
O3 C8 C7 124.5(3)
O3 C8 C9 114.8(3)
C7 C8 C9 120.7(4)
O4 C6 N2 123.4(3)
O4 C6 C7 121.0(3)
N2 C6 C7 115.6(3)
N1 C1 C2 118.6(3)
N1 C1 N2 115.1(3)
C2 C1 N2 126.2(3)
C8 C7 N3 119.5(3)
C8 C7 C6 122.2(3)
N3 C7 C6 118.3(3)
N1 C5 C4 120.0(4)
N1 C5 H5 120.0
C4 C5 H5 120.0
C10 C9 C8 124.0(3)
C10 C9 S2 111.5(3)
C8 C9 S2 124.4(3)
C11 C12 Cl22 127.1(3)
C11 C12 S2 113.6(3)
Cl22 C12 S2 119.3(2)
C3 C2 C1 118.9(4)
C3 C2 H2 120.6
C1 C2 H2 120.6
C12 C11 C10 109.9(4)
C12 C11 H11 125.1
C10 C11 H11 125.1
N3 C13 H13A 109.5
N3 C13 H13B 109.5
H13A C13 H13B 109.5
N3 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C9 C10 C11 114.6(4)
C9 C10 S1 116.5(3)
C11 C10 S1 128.9(3)
C5 C4 C3 118.8(4)
C5 C4 H4 120.6
C3 C4 H4 120.6
C4 C3 C2 121.3(4)
C4 C3 H3 119.4
C2 C3 H3 119.4
S3 C14 H14A 109.5
S3 C14 H14B 109.5
H14A C14 H14B 109.5
S3 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S3 O6 1.445(3)
S3 O7 1.466(3)
S3 O5 1.471(2)
S3 C14 1.761(4)
S1 O2 1.424(3)
S1 O1 1.430(3)
S1 N3 1.644(3)
S1 C10 1.757(4)
S2 C9 1.711(4)
S2 C12 1.720(4)
Cl22 C12 1.707(4)
O3 C8 1.344(4)
O3 H3A 0.8200
N1 C1 1.347(4)
N1 C5 1.353(4)
N1 H1 0.8600
N2 C6 1.369(4)
N2 C1 1.387(4)
N2 H2A 0.8600
N3 C7 1.435(4)
N3 C13 1.488(4)
O4 C6 1.233(4)
C8 C7 1.356(5)
C8 C9 1.455(5)
C6 C7 1.452(5)
C1 C2 1.384(5)
C5 C4 1.358(6)
C5 H5 0.9300
C9 C10 1.351(5)
C12 C11 1.358(5)
C2 C3 1.376(5)
C2 H2 0.9300
C11 C10 1.412(5)
C11 H11 0.9300
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C4 C3 1.369(5)
C4 H4 0.9300
C3 H3 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139147265
