Crystal engineering of pharmaceutical co-crystals from polymorphic active pharmaceutical ingredients
Vishweshwar, Peddy; McMahon, Jennifer A.; Peterson, Matthew L.; Hickey, Magali B.; Shattock, Tanise R.; Zaworotko, Michael J.; Chemical Communications  (2005) 4601–4603; doi:10.1039/b501304f

data_7111484
_publ_section_title
;
 Crystal engineering of pharmaceutical co-crystals from polymorphic active
 pharmaceutical ingredients
;
_journal_issue                   36
_journal_name_full               'Chemical Communications'
_journal_page_first              4601
_journal_page_last               4603
_journal_paper_doi               10.1039/b501304f
_journal_year                    2005
_chemical_formula_moiety         'C6 H10 N2 O2, C7 H6 O3'
_chemical_formula_sum            'C13 H16 N2 O5'
_chemical_formula_weight         280.28
_chemical_melting_point          416
_chemical_name_common
;1:1 Co-crystal of 2-Oxo-1-pyrrolidinyl)acetamide and 4-
Hydroxybenzoic acid
;
_chemical_name_systematic
;
1:1 Co-crystal of 2-Oxo-1-pyrrolidinyl)acetamide and 4-Hydroxybenzoic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.557(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.780(3)
_cell_length_b                   5.5029(12)
_cell_length_c                   17.068(4)
_cell_measurement_temperature    100(2)
_cell_volume                     1308.1(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0548
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4995
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.593
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_preparation       Acetonitrile
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0508P)^2^+0.6752P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1347
_reflns_number_gt                1753
_reflns_number_total             2220
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b501304fsup1.cif
_cod_data_source_block           jam624c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '416 K' was changed to '416' - the
value should be numeric and without a unit
designator.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1308.0(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7111484