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_4121331
_publ_contact_author_address
;
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
;
 Cocrystals of Nicotinamide and (R)-Mandelic Acid in Many Ratios with
 Anomalous Formation Properties
;
_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 unk
_chemical_formula_moiety         'C8 H8 O3'
_chemical_formula_sum            'C8 H8 O3'
_chemical_formula_weight         152.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2012-09-11
_audit_creation_method
;
  Olex2 1.2-alpha
  (compiled Sep  7 2012 17:37:03, GUI svn.r4339)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.08(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.377(4)
_cell_length_b                   5.859(2)
_cell_length_c                   15.047(5)
_cell_measurement_reflns_used    7114
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.753
_cell_measurement_theta_min      3.015
_cell_volume                     719.4(5)
_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 1.000
_diffrn_measured_fraction_theta_max 0.992
_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_R_equivalents  0.0204
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15607
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.267
_diffrn_reflns_theta_min         3.015
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_type              'Siemens, K FFCU 2K 90'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.910
_exptl_absorpt_correction_T_max  0.9527
_exptl_absorpt_correction_T_min  0.8471
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
? was used for absorption correction.
wR2(int) was 0.0503 before and 0.0350 after correction.
The Ratio of minimum to maximum transmission is 0.8892.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2773
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0284
_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^)+(0.0508P)^2^+0.0892P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0802
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                2568
_reflns_number_total             2773
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja4103887_si_004.cif
_cod_data_source_block           yu07
_cod_database_code               4121331
_diffrn_reflns_sigmai/neti       0.0140
_olex2_refinement_description
;
1. others
 Fixed Sof: O1(1) H1(1) O2(1) O3(1) H3(1) C1(1) C2(1) H2(1) C3(1) C4(1) H4(1)
 C5(1) H5(1) C6(1) H6(1) C7(1) H7(1) C8(1) H8(1) O1A(1) H1A(1) O2A(1) O3A(1)
 H3A(1) C1A(1) C2A(1) H2A(1) C3A(1) C4A(1) H4A(1) C5A(1) H5A(1) C6A(1) H6A(1)
 C7A(1) H7A(1) C8A(1) H8A(1)
2.a Ternary CH refined with riding coordinates:
 C2(H2), C2A(H2A)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C4A(H4A), C5A(H5A), C6A(H6A),
 C7A(H7A), C8A(H8A)
;
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.811
_shelx_res_checksum              10666
_shelxl_version_number           2012-4