Crystal structure, interaction energies and experimental electron density of the popular drug ketoprophen
Pawledzio, Sylwia; Makal, Anna; Trzybiński, Damian; Woźniak, Krzysztof; IUCrJ 5 (2018) –; doi:10.1107/S2052252518013222

data_1550147
_publ_section_title
;
 Crystal structure, interaction energies and experimental electron density
 of the popular drug ketoprophen
;
_journal_issue                   6
_journal_name_full               IUCrJ
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052252518013222
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H14 O3'
_chemical_formula_sum            'C16 H14 O3'
_chemical_formula_weight         254.27
_chemical_name_systematic        '2-(3-benzoylphenyl)-propionic acid'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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
_audit_creation_date             2018-06-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.1130(5)
_cell_length_b                   7.3809(6)
_cell_length_c                   55.524(5)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    100
_cell_measurement_theta_max      37.961
_cell_measurement_theta_min      2.933
_cell_volume                     2505.2(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.03
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       83
_diffrn_reflns_limit_l_min       -103
_diffrn_reflns_number            66457
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         45.526
_diffrn_reflns_theta_min         1.467
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9339
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0653 before and 0.0530 after correction.
The Ratio of minimum to maximum transmission is 0.9339.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.287
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Flack x determined using 3482 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         17839
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0720P)^2^+0.1836P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1604
_reflns_Friedel_coverage         0.662
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.755
_reflns_number_gt                11356
_reflns_number_total             17839
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lq5013.cif
_cod_data_source_block           2016_03_20_am_ketsigma_0m
_cod_database_code               1550147
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O2A-H2A
 0.84 with sigma of 0.02
 O2B-H2B
 0.84 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C8A(H8A), C8B(H8B)
3.b Aromatic/amide H refined with riding coordinates:
 C2A(H2AA), C4A(H4A), C5A(H5A), C6A(H6A), C12A(H12A), C13A(H13A), C14A(H14A),
 C15A(H15A), C16A(H16A), C2B(H2BA), C4B(H4B), C5B(H5B), C6B(H6B), C12B(H12B),
 C13B(H13B), C14B(H14B), C15B(H15B), C16B(H16B)
3.c Idealised Me refined as rotating group:
 C9A(H9AA,H9AB,H9AC), C9B(H9BA,H9BB,H9BC)
3.d Idealised tetrahedral OH refined as rotating group:
 O2A(H2A), O2B(H2B)
;
_olex2_submission_special_instructions 'No special instructions were received'