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_7209754
_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         'C14 H14 O3, C5 H9 N O2'
_chemical_formula_sum            'C19 H23 N O5'
_chemical_formula_weight         345.38
_chemical_name_common
;
D-Prolinium cocrystal of S-Naproxen
;
_chemical_name_systematic
;
(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid -
R-pyrrolidinium-2-carboxylate (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
_cell_angle_alpha                90.00
_cell_angle_beta                 92.047(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.7713(2)
_cell_length_b                   6.2520(3)
_cell_length_c                   23.8346(11)
_cell_measurement_reflns_used    1815
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.5182
_cell_measurement_theta_min      3.7093
_cell_volume                     859.46(6)
_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)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3712
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            3519
_diffrn_reflns_theta_full        67.59
_diffrn_reflns_theta_max         67.59
_diffrn_reflns_theta_min         3.71
_exptl_absorpt_coefficient_mu    0.795
_exptl_absorpt_correction_T_max  0.9765
_exptl_absorpt_correction_T_min  0.6920
_exptl_absorpt_correction_type   analytical
_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)
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)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plaquet
_exptl_crystal_F_000             368
_exptl_crystal_preparation       ethanol
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2233
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0658
_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
'calc w=1/[\s^2^(Fo^2^)+(0.0904P)^2^+0.6329P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1795
_refine_ls_wR_factor_ref         0.1811
_reflns_number_gt                2141
_reflns_number_total             2233
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce40084k.txt
_cod_data_source_block           shelxl2
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7209754