Cocrystals of Nicotinamide and (R)-Mandelic Acid in Many Ratios with Anomalous Formation Properties
Si-Wei Zhang; Michelle T. Harasimowicz; Melgardt M. de Villiers; Lian Yu; Journal of the American Chemical Society 135 (2013) 18981–18989; doi:10.1021/ja4103887

data_4121372
_publ_contact_author_address
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4119 Rennebohm Hall
777 Highland Avenue
Madison, WI 53705
;
_publ_contact_author_email       lyu@pharmacy.wisc.edu
_publ_contact_author_name        'Lian Yu'
_publ_section_title
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 Cocrystals of Nicotinamide and (R)-Mandelic Acid in Many Ratios with
 Anomalous Formation Properties
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_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18981
_journal_page_last               18989
_journal_paper_doi               10.1021/ja4103887
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C6 H6 N2 O, 2(C8 H8 O3)'
_chemical_formula_sum            'C22 H22 N2 O7'
_chemical_formula_weight         426.41
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-02-15
_audit_creation_method
;
  Olex2 1.2-alpha
  (compiled Nov  5 2012 18:25:38, GUI svn.r4372)
;
_cell_angle_alpha                97.770(5)
_cell_angle_beta                 91.964(4)
_cell_angle_gamma                90.557(5)
_cell_formula_units_Z            2
_cell_length_a                   6.5020(12)
_cell_length_b                   7.5220(8)
_cell_length_c                   20.6532(17)
_cell_measurement_reflns_used    9586
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      70.15
_cell_measurement_theta_min      4.32
_cell_volume                     1000.1(2)
_computing_cell_refinement       'SAINT+ Ver. 7.68A (Bruker-AXS, 2009)'
_computing_data_collection       'APEX2 Ver. 2012.14-3 (Bruker-AXS, 2012)'
_computing_data_reduction        'SAINT+ Ver. 7.68A'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008-2012)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.60\% \w and 0.6\% \f scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'equatorially mounted graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            54853
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         72.437
_diffrn_reflns_theta_min         2.160
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_type              'Siemens, K FFCU 2K 90'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.893
_exptl_absorpt_correction_T_max  0.6865
_exptl_absorpt_correction_T_min  0.6182
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0454 before and 0.0332 after correction.
The Ratio of minimum to maximum transmission is 0.9005.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.352
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.07(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     608
_refine_ls_number_reflns         7540
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0270
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.1219P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0762
_reflns_Friedel_coverage         0.950
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.928
_reflns_number_gt                7297
_reflns_number_total             7540
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja4103887_si_003.cif
_cod_data_source_block           yu10
_cod_database_code               4121372
_cod_database_fobs_code          4121372
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H3A of C3A, H2AC of C2A, H1A of C1A, H5A of C5A, H7D of C7D, H8D of C8D,
  H9D of C9D, H11D of C11D, H12D of C12D, H13D of C13D, H12A of C12A, H13A of
  C13A, H7B of C7B, H8B of C8B, H9B of C9B, H11B of C11B, H12B of C12B, H13B of
  C13B, H13C of C13C, H12C of C12C, H11C of C11C, H9C of C9C, H8C of C8C, H7C
  of C7C, H11A of C11A, H9A of C9A, H8A of C8A, H7A of C7A, H5B of C5B, H3B of
  C3B, H2BC of C2B, H1B of C1B
2.a Ternary CH refined with riding coordinates:
 C13A(H13A), C13B(H13B), C13C(H13C), C13D(H13D)
2.b Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C2A(H2AC), C3A(H3A), C5A(H5A), C1B(H1B), C2B(H2BC), C3B(H3B),
 C5B(H5B), C7A(H7A), C8A(H8A), C9A(H9A), C11A(H11A), C12A(H12A), C7B(H7B),
 C8B(H8B), C9B(H9B), C11B(H11B), C12B(H12B), C7C(H7C), C8C(H8C), C9C(H9C),
 C11C(H11C), C12C(H12C), C7D(H7D), C8D(H8D), C9D(H9D), C11D(H11D), C12D(H12D)
;
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.744
_shelxl_version_number           2012-6