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_7235093
_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), 2(C5 H9 N O2), C H4 O'
_chemical_formula_sum            'C39 H50 N2 O11'
_chemical_formula_weight         722.81
_chemical_name_common
;
1:1 RS-naproxen D-proline cocrystal methanol solvate 
;
_chemical_name_systematic
;
(2R)-2-(6-methoxynaphthalen-2-yl)propanoic acid;
 bis((2R)-pyrrolidine-2-carboxylic acid); 
(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid; methanol
;
_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     dual
_atom_sites_solution_secondary   difmap
_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                 93.984(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.9532(4)
_cell_length_b                   5.76337(15)
_cell_length_c                   25.2764(6)
_cell_measurement_reflns_used    5523
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      66.9150
_cell_measurement_theta_min      3.4980
_cell_volume                     1882.43(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      295(2)
_diffrn_detector_area_resol_mean 5.1856
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur, Ruby, Gemini ultra
;
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11648
_diffrn_reflns_point_group_measured_fraction_full 0.836
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        67.194
_diffrn_reflns_theta_max         67.194
_diffrn_reflns_theta_min         3.420
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.768
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       needle
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         5615
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0892P)^2^+0.2271P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1532
_reflns_Friedel_coverage         0.523
_reflns_Friedel_fraction_full    0.645
_reflns_Friedel_fraction_max     0.645
_reflns_number_gt                4791
_reflns_number_total             5615
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce01338a2.cif
_cod_data_source_block           nt0025_RSnprxDproMeOHb4
_cod_original_cell_volume        1882.42(9)
_cod_database_code               7235093
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.705
_shelx_estimated_absorpt_t_max   0.963
_shelx_res_checksum              10157