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_7228273
_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, 2(C5 H9 N O)'
_chemical_formula_sum            'C22 H27 N5 O7'
_chemical_formula_weight         473.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_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                78.832(12)
_cell_angle_beta                 81.329(11)
_cell_angle_gamma                75.997(12)
_cell_formula_units_Z            2
_cell_length_a                   6.9119(8)
_cell_length_b                   11.5956(17)
_cell_length_c                   15.219(2)
_cell_measurement_reflns_used    1071
_cell_measurement_temperature    170.2(4)
_cell_measurement_theta_max      25.9490
_cell_measurement_theta_min      1.8910
_cell_volume                     1154.2(3)
_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      170.2(4)
_diffrn_detector_area_resol_mean 16.1593
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -71.00  -43.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1690 -178.0000  -60.0000 28

  2 omega  -20.00    7.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1690  -99.0000 -180.0000 27

  3 omega  -18.00   24.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1690  -99.0000    0.0000 42

  4 omega   -4.00   87.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690   38.0000    0.0000 91

  5 omega   37.00   95.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690  178.0000 -150.0000 58

  6 omega    0.00   87.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690   38.0000  -90.0000 87

  7 omega  -50.00   -9.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690  -38.0000 -180.0000 41
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0095130000
_diffrn_orient_matrix_UB_12      0.0253854000
_diffrn_orient_matrix_UB_13      -0.0458663000
_diffrn_orient_matrix_UB_21      -0.0181047000
_diffrn_orient_matrix_UB_22      0.0586213000
_diffrn_orient_matrix_UB_23      0.0110894000
_diffrn_orient_matrix_UB_31      0.1044144000
_diffrn_orient_matrix_UB_32      -0.0018091000
_diffrn_orient_matrix_UB_33      -0.0075710000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.1020
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6598
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         1.83
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68826
_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    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.812
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1286
_refine_ls_R_factor_gt           0.0916
_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/[\s^2^(Fo^2^)+(0.1525P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2269
_refine_ls_wR_factor_ref         0.2584
_reflns_number_gt                2126
_reflns_number_total             3317
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ce00303j2.cif
_cod_data_source_block           exp_3018
_cod_database_code               7228273
_chemical_oxdiff_formula         'C22 H27 N5 O7'
_reflns_odcompleteness_completeness 99.87
_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 C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 O1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C19(H19A,H19B), C20(H20A,
 H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C22(H22A,H22B,H22C)
;
_olex2_date_sample_data_collection 2015-01-27
_olex2_submission_special_instructions 'No special instructions were received'