Co-crystallization of anti-inflammatory pharmaceutical contaminants and rare carboxylic acid‒pyridine supramolecular synthon breakdown
Zheng, Qixuan; Rood, Samantha L.; Unruh, Daniel K.; Hutchins, Kristin M.; CrystEngComm 20 (2018) 6377–; doi:10.1039/C8CE01492B

data_7231590
_publ_section_title
;
 Co-crystallization of anti-inflammatory pharmaceutical contaminants and
 rare carboxylic acid--pyridine supramolecular synthon breakdown
;
_journal_issue                   41
_journal_name_full               CrystEngComm
_journal_page_first              6377
_journal_paper_doi               10.1039/C8CE01492B
_journal_volume                  20
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_sum            'C40 H40 N2 O6'
_chemical_formula_weight         644.74
_chemical_name_systematic
'co-crystal of naproxen and 1,2-Bis(4-pyridyl)ethane'
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-03-14T15:11:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2018-08-30 deposited with the CCDC.
2018-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.646(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   38.014(16)
_cell_length_b                   5.787(3)
_cell_length_c                   15.566(7)
_cell_measurement_reflns_used    4039
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      24.88
_cell_measurement_theta_min      2.60
_cell_volume                     3417(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      160(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17520
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.414
_diffrn_reflns_theta_min         1.073
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       blade
_exptl_crystal_F_000             1368
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene'
_exptl_crystal_size_max          0.485
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1789 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         6219
_refine_ls_number_restraints     557
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0458P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0949
_reflns_number_gt                4854
_reflns_number_total             6219
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce01492b2.cif
_cod_data_source_block           naproxenBPEth
_cod_depositor_comments
'Adding full bibliography for 7231588--7231594.cif.'
_cod_original_cell_volume        3418(3)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7231590
_shelx_estimated_absorpt_t_min   0.96
_shelx_estimated_absorpt_t_max   0.996
_shelx_res_checksum              16062