SCXRD, CSP-NMRX and microED in the quest for three elusive polymorphs of meloxicam.
Jeziorna, Agata; Malinska, Maura; Sugden, Isaac; Paluch, Piotr; Dolot, Rafał; Dudek, Marta K.; IUCrJ 12 (2025) –; doi:10.1107/S2052252524011898

data_1573579
_publ_section_title
;
 SCXRD, CSP-NMRX and microED in the quest for three elusive polymorphs of
 meloxicam.
;
_journal_coeditor_code           ED5031
_journal_issue                   1
_journal_name_full               IUCrJ
_journal_paper_doi               10.1107/S2052252524011898
_journal_volume                  12
_journal_year                    2025
_chemical_compound_source        'Meloxicam was purchased from ABCR'
_chemical_formula_moiety         'C14 H13 N3 O4 S2'
_chemical_formula_sum            'C14 H13 N3 O4 S2'
_chemical_formula_weight         351.39
_chemical_name_common            meloxicam
_chemical_name_systematic
4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-2H-1,2-benzothiazine-3-carboxamide
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-16
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-04-16 deposited with the CCDC. 2024-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                65.901(2)
_cell_angle_beta                 87.2540(10)
_cell_angle_gamma                79.4390(10)
_cell_formula_units_Z            4
_cell_length_a                   11.2439(2)
_cell_length_b                   11.2772(2)
_cell_length_c                   13.4027(2)
_cell_measurement_reflns_used    21943
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.4330
_cell_measurement_theta_min      3.6050
_cell_volume                     1524.37(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.100a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.100a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.100a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -30.00  19.00   0.50    0.51    --  -43.96  79.00 -87.00   98
  2  \w    -64.00 -38.00   0.50    0.51    --  -43.96  79.00 -87.00   52
  3  \w    -77.00 -51.00   0.50    2.03    --  -96.00  79.00 -87.00   52
  4  \w   -168.00-133.00   0.50    2.03    --  -96.00 -79.00 148.00   70
  5  \w     46.00  74.00   0.50    2.03    --  107.98 -79.00 148.00   56
  6  \w    133.00 163.00   0.50    2.03    --  107.98  79.00 -87.00   60
  7  \w    -23.00   2.00   0.50    0.51    --   12.00 101.00 135.78   50
  8  \w    -13.00  13.00   0.50    0.51    --   12.00  82.00 -38.58   52
  9  \w    -10.00  15.00   0.50    0.51    --   16.00  83.00-167.45   50
 10  \w     -2.00  23.00   0.50    0.51    --   20.00  74.00  16.44   50
 11  \w      0.00  25.00   0.50    0.51    --   20.00  71.00  54.43   50
 12  \w     15.00  40.00   0.50    0.51    --   32.00  64.00-159.01   50
 13  \w     15.00  40.00   0.50    0.51    --   32.00  64.00 -34.80   50
 14  \w     15.00  41.00   0.50    0.51    --   32.00  65.00  41.24   52
 15  \w     14.00  39.00   0.50    0.51    --   32.00  66.00-122.88   50
 16  \w     19.00  44.00   0.50    0.51    --   36.00  63.00 142.78   50
 17  \w     38.00  92.00   0.50    0.51    --   43.96-125.00 -90.00  108
 18  \w      3.00  61.00   0.50    0.51    --   43.96 -79.00 148.00  116
 19  \w    -14.00  16.00   0.50    0.51    --   43.96 -38.00-150.00   60
 20  \w     32.00  57.00   0.50    0.51    --   43.96  58.00  90.28   50
 21  \w     29.00  54.00   0.50    0.51    --   43.96  59.00 -89.32   50
 22  \w     27.00  78.00   0.50    0.51    --   43.96 -99.00   0.00  102
 23  \w     28.00  53.00   0.50    0.51    --   43.96  60.00 -80.25   50
 24  \w     28.00  53.00   0.50    0.51    --   43.96  60.00 -61.98   50
 25  \w     30.00  57.00   0.50    0.51    --   44.00  60.00-125.45   54
 26  \w     28.00  53.00   0.50    0.51    --   44.00  61.00  70.86   50
 27  \w     28.00  53.00   0.50    0.51    --   44.00  61.00  20.21   50
 28  \w     28.00  53.00   0.50    0.51    --   44.00  61.00  -5.20   50
 29  \w     28.00  53.00   0.50    0.51    --   44.00  61.00 165.68   50
 30  \w     33.00  58.00   0.50    0.51    --   48.00  59.00-154.97   50
 31  \w     33.00  58.00   0.50    0.51    --   48.00  59.00 -39.20   50
 32  \w     33.00  58.00   0.50    0.51    --   48.00  59.00 126.14   50
 33  \w    -84.00 -42.00   0.50    0.51    --  -56.00 -52.00-177.88   84
 34  \w   -129.00 -97.00   0.50    0.51    --  -56.00 -50.00 -41.37   64
 35  \w    -68.00 -42.00   0.50    0.51    --  -56.00 -51.00  63.66   52
 36  \w   -127.00 -99.00   0.50    0.51    --  -56.00 -52.00-177.88   56
 37  \w    -72.00 -41.00   0.50    0.51    --  -56.00 -50.00 -41.37   62
 38  \w   -126.00-100.00   0.50    0.51    --  -60.00 -52.00  -7.01   52
 39  \w    -73.00 -47.00   0.50    0.51    --  -60.00 -52.00  -7.01   52
 40  \w   -119.00 -94.00   0.50    0.51    --  -64.00 -48.00-111.45   50
 41  \w    -87.00 -50.00   0.50    0.51    --  -64.00 -48.00-111.45   74
 42  \w    -87.00 -54.00   0.50    0.51    --  -68.00 -52.00 -82.66   66
 43  \w    -91.00 -56.00   0.50    0.51    --  -68.00 -52.00-140.98   70
 44  \w    -81.00 -55.00   0.50    0.51    --  -68.00 -51.00  41.34   52
 45  \w    -87.00 -55.00   0.50    0.51    --  -68.00 -52.00-126.49   64
 46  \w    -84.00 -58.00   0.50    2.03    --  -72.00 -51.00   2.85   52
 47  \w   -144.00-118.00   0.50    2.03    --  -72.00 -46.00 -70.75   52
 48  \w    -85.00 -59.00   0.50    2.03    --  -72.00 -46.00 -70.75   52
 49  \w   -120.00 -94.00   0.50    2.03    --  -72.00 -51.00 165.00   52
 50  \w    -83.00 -58.00   0.50    2.03    --  -72.00 -51.00 148.84   50
 51  \w    -86.00 -58.00   0.50    2.03    --  -72.00 -50.00 -32.46   56
 52  \w    -88.00 -58.00   0.50    2.03    --  -72.00 -50.00  29.28   60
 53  \w    -84.00 -58.00   0.50    2.03    --  -72.00 -51.00 165.00   52
 54  \w    -84.00 -58.00   0.50    2.03    --  -72.00 -51.00-110.68   52
 55  \w    -89.00 -63.00   0.50    2.03    --  -76.00 -51.00 120.13   52
 56  \w    -91.00 -65.00   0.50    2.03    --  -76.00 -51.00 105.06   52
 57  \w    -87.00 -62.00   0.50    2.03    --  -76.00 -52.00  80.33   50
 58  \w    -91.00 -66.00   0.50    2.03    --  -80.00 -52.00-145.83   50
 59  \w    -92.00 -66.00   0.50    2.03    --  -80.00 -51.00 -37.09   52
 60  \w    -92.00 -67.00   0.50    2.03    --  -80.00 -52.00  93.18   50
 61  \w    -93.00 -67.00   0.50    2.03    --  -80.00 -52.00-167.99   52
 62  \w    -92.00 -66.00   0.50    2.03    --  -80.00 -50.00 137.01   52
 63  \w   -101.00 -75.00   0.50    2.03    --  -88.00 -49.00 -30.91   52
 64  \w   -101.00 -75.00   0.50    2.03    --  -88.00 -51.00  74.57   52
 65  \w   -122.00 -86.00   0.50    2.03    --  -96.00 -60.00  26.00   72
 66  \w   -154.00-127.00   0.50    2.03    --  -96.00 -60.00  26.00   54
 67  \w   -115.00 -83.00   0.50    2.03    --  -96.00 -57.00-177.76   64
 68  \w   -169.00-140.00   0.50    2.03    --  -96.00 -57.00-177.76   58
 69  \w   -113.00 -84.00   0.50    2.03    --  -96.00 -57.00 137.23   58
 70  \w   -126.00 -84.00   0.50    2.03    --  -96.00 -57.00-139.88   84
 71  \w   -168.00-136.00   0.50    2.03    --  -96.00 -57.00-139.88   64
 72  \w   -169.00 -83.00   0.50    2.03    --  -96.00 -55.00 108.87  172
 73  \w   -111.00 -85.00   0.50    2.03    --  -96.00 -56.00  78.80   52
 74  \w   -167.00-127.00   0.50    2.03    --  -96.00 -56.00  78.80   80
 75  \w   -120.00 -83.00   0.50    2.03    --  -96.00 -54.00  29.61   74
 76  \w   -111.00 -84.00   0.50    2.03    --  -96.00 -58.00 -34.49   54
 77  \w   -169.00-129.00   0.50    2.03    --  -96.00 -54.00  29.61   80
 78  \w   -150.00-117.00   0.50    2.03    --  -96.00 -58.00 -34.49   66
 79  \w   -110.00 -84.00   0.50    2.03    --  -96.00 -58.00  53.85   52
 80  \w   -121.00 -84.00   0.50    2.03    --  -96.00 -59.00 157.19   74
 81  \w   -169.00-128.00   0.50    2.03    --  -96.00 -59.00 157.19   82
 82  \w   -167.00-131.00   0.50    2.03    --  -96.00 -54.00  66.35   72
 83  \w   -113.00 -85.00   0.50    2.03    --  -96.00 -60.00 -96.68   56
 84  \w   -154.00-128.00   0.50    2.03    --  -96.00 -60.00 -96.68   52
 85  \w   -117.00 -87.00   0.50    2.03    --  -96.00 -61.00-120.00   60
 86  \w   -164.00-138.00   0.50    2.03    --  -96.00 -61.00-120.00   52
 87  \w   -170.00 -84.00   0.50    2.03    --  -96.00 -58.00 -49.27  172
 88  \w   -125.00 -86.00   0.50    2.03    --  -96.00 -54.00   6.87   78
 89  \w   -169.00-138.00   0.50    2.03    --  -96.00 -54.00   6.87   62
 90  \w   -111.00 -85.00   0.50    2.03    --  -96.00 -60.00 133.56   52
 91  \w   -151.00-125.00   0.50    2.03    --  -96.00 -60.00 133.56   52
 92  \w   -117.00 -87.00   0.50    2.03    --  -96.00 -61.00-180.00   60
 93  \w   -112.00 -83.00   0.50    2.03    --  -96.00 -55.00 -84.89   58
 94  \w    -51.00 -25.00   0.50    2.03    --  -96.00  61.00-150.00   52
 95  \w   -160.00-134.00   0.50    2.03    --  -96.00 -55.00 -84.89   52
 96  \w   -115.00 -83.00   0.50    2.03    --  -96.00 -56.00-112.68   64
 97  \w   -167.00-127.00   0.50    2.03    --  -96.00 -56.00-112.68   80
 98  \w   -110.00 -84.00   0.50    2.03    --  -96.00 -53.00-158.94   52
 99  \w   -167.00 -84.00   0.50    2.03    --  -96.00 -58.00  98.22  166
100  \w   -111.00 -86.00   0.50    2.03    --  -96.00 -54.00  66.35   50
101  \w   -115.00 -86.00   0.50    2.03    --  -96.00 -58.00 -18.96   58
102  \w   -157.00-131.00   0.50    2.03    --  -96.00 -58.00 -18.96   52
103  \w   -169.00 -84.00   0.50    2.03    --  -96.00 -59.00 -62.64  170
104  \w   -168.00-139.00   0.50    2.03    --  -96.00 -53.00-158.94   58
105  \w     65.00  99.00   0.50    2.03    --  107.98 -95.00 -30.00   68
106  \w     34.00  60.00   0.50    2.03    --  107.98 -95.00 -30.00   52
107  \w     63.00  96.00   0.50    2.03    --  107.98 -95.00   0.00   66
108  \w     73.00  99.00   0.50    2.03    --  107.98-100.00 134.23   52
109  \w     35.00  60.00   0.50    2.03    --  107.98 -95.00   0.00   50
110  \w     34.00  67.00   0.50    2.03    --  107.98-100.00 134.23   66
111  \w     35.00  94.00   0.50    2.03    --  107.98 -95.00-120.00  118
112  \w     58.00 101.00   0.50    2.03    --  107.98-125.00 150.00   86
113  \w     68.00  96.00   0.50    2.03    --  107.98 -95.00  30.00   56
114  \w     48.00  93.00   0.50    2.03    --  107.98 -95.00 -90.00   90
115  \w     35.00  86.00   0.50    2.03    --  107.98 -95.00-150.00  102
116  \w     38.00  64.00   0.50    2.03    --  107.98 -95.00  30.00   52
117  \w     34.00  95.00   0.50    2.03    --  107.98 -95.00 -60.00  122
118  \w     66.00  99.00   0.50    2.03    --  107.98 -95.00-180.00   66
119  \w     74.00  99.00   0.50    2.03    --  107.98 -95.00  60.00   50
120  \w     36.00  64.00   0.50    2.03    --  107.98 -95.00  60.00   56
121  \w     37.00  94.00   0.50    2.03    --  107.98 -95.00 150.00  114
122  \w     42.00  68.00   0.50    2.03    --  107.98 -77.00  60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0903680000
_diffrn_orient_matrix_UB_12      -0.0460304000
_diffrn_orient_matrix_UB_13      0.0920157000
_diffrn_orient_matrix_UB_21      0.0861459000
_diffrn_orient_matrix_UB_22      -0.1334181000
_diffrn_orient_matrix_UB_23      0.0548900000
_diffrn_orient_matrix_UB_31      0.0620900000
_diffrn_orient_matrix_UB_32      0.0567692000
_diffrn_orient_matrix_UB_33      0.0662574000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            37137
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.590
_diffrn_reflns_theta_min         3.614
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.396
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.100a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_preparation       'Meloxicam was purchased from ABCR.'
_exptl_crystal_recrystallization_method
'Obtained by desolvatation of meloxicam:DMSO crystals.'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.00055(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     422
_refine_ls_number_reflns         5933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0353P)^2^+1.7993P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0915
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5425
_reflns_number_total             5933
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ed5031.cif
_cod_data_source_block           I
_cod_database_code               1573579
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S'
_shelx_estimated_absorpt_t_max   0.876
_shelx_estimated_absorpt_t_min   0.667
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C12(H12), N22(H22), C22(H22A),
 C23(H23), C24(H24), C25(H25), C32(H32)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C14(H14A,H14B,H14C), C29(H29A,H29B,H29C), C34(H34A,H34B,H34C)
2.c Idealised tetrahedral OH refined as rotating group:
 O7(H7), O27(H27)
;
_shelx_res_checksum              91462
_shelx_hkl_checksum              6508
_olex2_exptl_crystal_mounting_method
'Crystal was glued to a support using the silicone grease.'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.831
_oxdiff_exptl_absorpt_empirical_full_min 0.598