Bringing new life into old drugs. A case study on nifuroxazide polymorphism
Covaci, Ovidiu Ilie; Mitran, Raul - Augustin Augustin; Buhalteanu, Lucian; Dumitrescu, Dan; Sova, Sergiu; Manta, Corina Mihaela; CrystEngComm  (2017) –; doi:10.1039/C7CE00303J

data_7228271
_publ_section_title
;
 Bringing new life into old drugs. A case study on nifuroxazide
 polymorphism
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE00303J
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C12 H9 N3 O5, C4 H9 N O'
_chemical_formula_sum            'C16 H18 N4 O6'
_chemical_formula_weight         362.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-11-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-11-09 deposited with the CCDC.
2017-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.655(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.0499(9)
_cell_length_b                   6.4263(4)
_cell_length_c                   10.3169(7)
_cell_measurement_reflns_used    2147
_cell_measurement_temperature    169.9(4)
_cell_measurement_theta_max      25.4020
_cell_measurement_theta_min      1.5740
_cell_volume                     864.27(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2008 (Burla et al., 2007)'
_diffrn_ambient_temperature      169.9(4)
_diffrn_detector_area_resol_mean 16.1593
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -93.00  -51.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1690 -178.0000  150.0000 42

  2 omega   57.00   92.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690  178.0000   60.0000 35

  3 omega   42.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690   57.0000  120.0000 44

  4 omega  -52.00   45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690  -38.0000    0.0000 97

  5 omega  -25.00   15.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690  -99.0000  -30.0000 40

  6 omega   44.00   82.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690   57.0000    0.0000 38

  7 omega   35.00   73.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690   57.0000 -180.0000 38

  8 omega  -53.00   33.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690  -19.0000 -180.0000 86
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0232207000
_diffrn_orient_matrix_UB_12      0.0913061000
_diffrn_orient_matrix_UB_13      0.0264207000
_diffrn_orient_matrix_UB_21      -0.0414144000
_diffrn_orient_matrix_UB_22      0.0122993000
_diffrn_orient_matrix_UB_23      0.0414762000
_diffrn_orient_matrix_UB_31      0.0265656000
_diffrn_orient_matrix_UB_32      -0.0607318000
_diffrn_orient_matrix_UB_33      0.0481868000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5906
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.56
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2684
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0492
_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/[\s^2^(Fo^2^)+(0.0660P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1264
_reflns_number_gt                2306
_reflns_number_total             2684
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ce00303j2.cif
_cod_data_source_block           shi_3008_iomi
_cod_original_cell_volume        864.28(10)
_cod_database_code               7228271
_chemical_oxdiff_formula         'C12 H12 N3 O3'
_chemical_oxdiff_usercomment     'SPS_1013 SCG_01a'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 N1(H1A), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_date_sample_data_collection 2015-01-26
_olex2_submission_special_instructions 'No special instructions were received'