Structural insight into cocrystallization with zwitterionic co-formers: cocrystals of S-naproxen
Tumanova, Natalia; Tumanov, Nikolay; Robeyns, Koen; Filinchuk, Yaroslav; Wouters, Johan; Leyssens, Tom; CrystEngComm 16 (2014) 8185–; doi:10.1039/C4CE00353E

data_7218005
_publ_section_title
;
 Structural insight into cocrystallization with zwitterionic co-formers:
 cocrystals of S-naproxen
;
_journal_issue                   35
_journal_name_full               CrystEngComm
_journal_page_first              8185
_journal_paper_doi               10.1039/C4CE00353E
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C14 H14 O3, C3 H7 N O2'
_chemical_formula_sum            'C17 H21 N O5'
_chemical_formula_weight         319.35
_chemical_name_common            'S-naproxen D-alanine'
_chemical_name_systematic
;
(+)-(S)-2-(6-methoxynaphthalen-2-yl) 
propanoic acid (R)-2-Aminopropionic acid
;
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3366(4)
_cell_length_b                   6.9013(6)
_cell_length_c                   44.227(4)
_cell_measurement_reflns_used    837
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.2049
_cell_measurement_theta_min      2.2974
_cell_volume                     1628.9(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies, Version 1.171.36.21
;
_computing_data_collection       MAR
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies, Version 1.171.36.21
;
_computing_molecular_graphics    'Mercury 3.1'
_computing_publication_material  enCIFer
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 6.6667
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '357 images, \D\F 0.5\% '
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0931
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            6347
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        20.772
_diffrn_reflns_theta_max         20.815
_diffrn_reflns_theta_min         2.763
_diffrn_source                   'Rigaku UltraX 18 rotating anode'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,Version 1.171.36.21
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       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.138
_refine_ls_abs_structure_details
;
 Flack x determined using 447 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         1712
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0833
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1297P)^2^+1.2178P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2141
_refine_ls_wR_factor_ref         0.2249
_reflns_Friedel_coverage         0.604
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                1424
_reflns_number_total             1712
_reflns_threshold_expression     'I > 2\s(I)'
_cod_duplicate_entry             7215888
_cod_data_source_file            c4ce00353e5.cif
_cod_data_source_block           S-naproxen_D-alanine
_cod_database_code               7218005
_shelx_estimated_absorpt_t_min   0.990
_shelx_estimated_absorpt_t_max   0.997
_shelxl_version_number           2013-4
_shelx_res_checksum              59179