Exploring polymorphism and stoichiometric diversity in naproxen/proline cocrystals
Tumanova, Natalia; Tumanov, Nikolay; Fischer, Franziska; Morelle, Fabrice; Ban, Voraksmy; Robeyns, Koen; Filinchuk, Yaroslav; Wouters, Johan; Emmerling, Franziska; Leyssens, Tom; CrystEngComm 20 (2018) 7308–; doi:10.1039/C8CE01338A

data_7235097
_publ_section_title
;
 Exploring polymorphism and stoichiometric diversity in naproxen/proline
 cocrystals
;
_journal_issue                   45
_journal_name_full               CrystEngComm
_journal_page_first              7308
_journal_paper_doi               10.1039/C8CE01338A
_journal_volume                  20
_journal_year                    2018
_chemical_absolute_configuration rm
_chemical_formula_moiety         '2(C14 H14 O3), 3(C5 H9 N O2)'
_chemical_formula_sum            'C43 H55 N3 O12'
_chemical_formula_weight         805.90
_chemical_name_common            'S-naproxen L-proline 2:3 cocrystal'
_chemical_name_systematic
'bis((2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid) tris((2S)-pyrrolidin-1-ium-2-carboxylate)'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2018-08-08 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.70180(10)
_cell_length_b                   18.8609(3)
_cell_length_c                   37.2392(5)
_cell_measurement_reflns_used    8552
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.1600
_cell_measurement_theta_min      1.7820
_cell_volume                     4004.74(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.865
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_device_type  'Pilatus 6M'
_diffrn_measurement_method       '\f scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.82656
_diffrn_reflns_av_R_equivalents  0.1298
_diffrn_reflns_av_unetI/netI     0.1120
_diffrn_reflns_Laue_measured_fraction_full 0.865
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            18663
_diffrn_reflns_point_group_measured_fraction_full 0.825
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_theta_full        28.657
_diffrn_reflns_theta_max         28.657
_diffrn_reflns_theta_min         1.787
_diffrn_source                   synchrotron
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       needle
_exptl_crystal_F_000             1720
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.011
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         5419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0642
_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^)+(0.0853P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1729
_reflns_Friedel_coverage         0.645
_reflns_Friedel_fraction_full    0.769
_reflns_Friedel_fraction_max     0.769
_reflns_number_gt                3761
_reflns_number_total             5419
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce01338a2.cif
_cod_data_source_block           Snprx-L_2-3
_cod_database_code               7235097
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.998
_shelx_res_checksum              27817