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_7228272
_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_formula_moiety         'C12 H9 N3 O5, C2 H6 O S, 0.5(H2 O)'
_chemical_formula_sum            'C14 H16 N3 O6.5 S'
_chemical_formula_weight         362.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.185(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.7327(7)
_cell_length_b                   10.8661(7)
_cell_length_c                   38.348(3)
_cell_measurement_reflns_used    2306
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      26.4260
_cell_measurement_theta_min      2.1190
_cell_volume                     3217.2(4)
_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  'ShelXH-1997 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector_area_resol_mean 16.1593
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   35.00   87.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690   57.0000 -150.0000 52

  2 omega    5.00   78.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690   57.0000  -60.0000 73

  3 omega   23.00   76.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690   57.0000    0.0000 53

  4 omega   23.00   62.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690  -99.0000   60.0000 39
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0480592000
_diffrn_orient_matrix_UB_12      0.0056523000
_diffrn_orient_matrix_UB_13      -0.0151231000
_diffrn_orient_matrix_UB_21      -0.0780917000
_diffrn_orient_matrix_UB_22      0.0082019000
_diffrn_orient_matrix_UB_23      -0.0103416000
_diffrn_orient_matrix_UB_31      0.0056586000
_diffrn_orient_matrix_UB_32      0.0645537000
_diffrn_orient_matrix_UB_33      0.0026665000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0936
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            11913
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.95
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87525
_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    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         5674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0597
_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^)+(0.0260P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.1067
_reflns_number_gt                3845
_reflns_number_total             5674
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ce00303j2.cif
_cod_data_source_block           shi_3009_iomi
_cod_depositor_comments
;

2017-11-21
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C12 H9 N3 O5), 2(C2 H6 O S), H2 O'
_cod_original_formula_sum        'C28 H32 N6 O13 S2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     724.72
_cod_database_code               7228272
_chemical_oxdiff_formula         'C12 H12 N3 O3 S1'
_chemical_oxdiff_usercomment     'sPS_1013 SCG_03b'
_reflns_odcompleteness_completeness 99.97
_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, All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Aromatic/amide H refined with riding coordinates:
 N1A(H1AA), C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A), C8A(H8A), C10A(H10A),
 C11A(H11A), N1B(H1BA), C2B(H2B), C3B(H3B), C5B(H5B), C6B(H6B), C8B(H8B),
 C10B(H10B), C11B(H11B)
2.c Idealised Me refined as rotating group:
 C13A(H13A,H13B,H13C), C14A(H14A,H14B,H14C), C13B(H13D,H13E,H13F), C14B(H14D,
 H14E,H14F)
2.d Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1B(H1B)
;
_olex2_date_sample_data_collection 2015-01-26
_olex2_submission_special_instructions 'No special instructions were received'