Naproxen–Nicotinamide Cocrystals: Racemic and Conglomerate Structures Generated by CO2Antisolvent Crystallization
Neurohr, Clémence; Marchivie, Mathieu; Lecomte, Sophie; Cartigny, Yohann; Couvrat, Nicolas; Sanselme, Morgane; Subra-Paternault, Pascale; Crystal Growth & Design 15 (2015) 4616–; doi:10.1021/acs.cgd.5b00876

data_4513532
_publ_section_title
;
 Naproxen--Nicotinamide Cocrystals: Racemic and Conglomerate Structures
 Generated by CO2Antisolvent Crystallization
;
_journal_issue                   9
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              4616
_journal_paper_doi               10.1021/acs.cgd.5b00876
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         '2(C14 H14 O3), C6 H6 N2 O'
_chemical_formula_sum            'C34 H34 N2 O7'
_chemical_formula_weight         582.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-05-27
_audit_creation_method
;
Olex2 1.2
(compiled Jan 19 2015 12:28:14 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.314(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0822(19)
_cell_length_b                   5.7965(11)
_cell_length_c                   32.892(4)
_cell_measurement_temperature    293
_cell_volume                     3025.8(8)
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.0
_diffrn_detector                 'CCD area detector'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Brucker Kappa CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1559
_diffrn_reflns_av_unetI/netI     0.0951
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            47104
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.252
_diffrn_reflns_theta_min         2.999
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.4606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1050 before and 0.0783 after correction.
The Ratio of minimum to maximum transmission is 0.6180.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       plate
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0035(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     395
_refine_ls_number_reflns         5408
_refine_ls_number_restraints     106
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1772
_refine_ls_R_factor_gt           0.0802
_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^)+(0.0633P)^2^+2.5259P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.1848
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2763
_reflns_number_total             5408
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cg5b00876_si_001.cif
_cod_data_source_block           sad
_cod_depositor_comments          'Adding full bibliography for 4513532.cif.'
_cod_database_code               4513532
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3.a Ternary CH refined with riding coordinates:
 C8(H8), C22(H22)
3.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C18(H18), C16(H16), C32(H32), C5(H5A), C29(H29), C25(H25), C15(H15),
  C26(H26), C3(H3), C2(H2C), C33(H33), C30(H30), C11(H11), C12(H12), C1(H1)
3.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
3.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C9(H9A,H9B,H9C), C34(H34A,H34B,H34C), C23(H23A,H23B,H23C)
3.e Idealised tetrahedral OH refined as rotating group:
 O5(H5), O2(H2)
;
_shelx_hkl_checksum              5466
_olex2_submission_special_instructions 'No special instructions were received'