On the influence of using a zwitterionic coformer for cocrystallization: structural focus on naproxen–proline cocrystals
Tilborg, Anaëlle; Springuel, Géraldine; Norberg, Bernadette; Wouters, Johan; Leyssens, Tom; CrystEngComm 15 (2013) 3341–; doi:10.1039/c3ce40084k

data_7209756
_publ_section_title
;
 On the influence of using a zwitterionic coformer for cocrystallization:
 structural focus on naproxen--proline cocrystals
;
_journal_issue                   17
_journal_name_full               CrystEngComm
_journal_page_first              3341
_journal_paper_doi               10.1039/c3ce40084k
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_moiety         C14H14O3,C5H9NO2,H2O
_chemical_formula_sum            'C19 H25 N O6'
_chemical_formula_weight         363.40
_chemical_name_common
;
L-Prolinium cocrystal of RS-Naproxen
;
_chemical_name_systematic
;
Pyrrolidinium-2-carboxylate-2-(6-methoxynaphthalen-2-yl)propanoic acid
hydrate(1:1:1)
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2012-12-11 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.560(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.122(2)
_cell_length_b                   5.8980(10)
_cell_length_c                   24.075(3)
_cell_measurement_reflns_used    3521
_cell_measurement_temperature    293(2)
_cell_volume                     1854.5(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3712
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            10708
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         29.1253
_diffrn_reflns_theta_min         3.3054
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_correction_T_min  0.9623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.832
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     530
_refine_ls_number_reflns         5930
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      0.837
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0686P)^2^+0.5674P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                5138
_reflns_number_total             5930
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce40084k.txt
_cod_data_source_block           test
_cod_original_formula_sum        'C19 H25 N1 O6'
_cod_database_code               7209756