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_1550146
_publ_section_title
;
 Crystal structure, interaction energies and experimental electron density
 of the popular drug ketoprophen
;
_journal_coeditor_code           LQ5013
_journal_issue                   6
_journal_name_full               IUCrJ
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052252518013222
_journal_volume                  5
_journal_year                    2018
_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      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_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                92.078(3)
_cell_angle_beta                 93.838(2)
_cell_angle_gamma                90.994(3)
_cell_formula_units_Z            2
_cell_length_a                   6.0671(4)
_cell_length_b                   7.5611(5)
_cell_length_c                   13.8523(9)
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.351
_cell_measurement_theta_min      3.023
_cell_volume                     633.49(7)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0291
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            96998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         45.599
_diffrn_reflns_theta_min         1.474
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.7142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0702 before and 0.0394 after correction.
The Ratio of minimum to maximum transmission is 0.9585.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.416
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.665
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         10775
_refine_ls_number_restraints     127
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0631P)^2^+0.0721P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1187
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8809
_reflns_number_total             10775
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lq5013.cif
_cod_data_source_block           2015_12_30_am_ket_0m
_cod_database_code               1550146
_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
 C3A-C2A \\sim C3C-C2C
 with sigma of 0.002
 C2C-C1C \\sim C2A-C1A
 with sigma of 0.002
 C6C-C1C \\sim C6A-C1A
 with sigma of 0.002
 C6C-C5C \\sim C6A-C5A
 with sigma of 0.002
 C5C-C4C \\sim C5A-C4A
 with sigma of 0.002
 C4A-C3A \\sim C4C-C3C
 with sigma of 0.002
 C8C-C1C \\sim C8A-C1A
 with sigma of 0.002
 C8A-C10A \\sim C8C-C10C
 with sigma of 0.002
 C7C-C3C \\sim C7A-C3A
 with sigma of 0.002
 O3A-C7A \\sim O3C-C7C
 with sigma of 0.002
3. Restrained planarity
 C1C, C2C, C3C, C4C, C5C, C6C
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
O1A \\sim O2A \\sim C8A \\sim C9A \\sim C10A: within 1.7A with sigma of 0.04
and sigma for terminal atoms of 0.08
5. Rigid body (RIGU) restrains
 C1C, C2C, C3C, C4C, C5C, C6C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O1C, O2C, O3C, C1C, C2C, C3C, C4C, C5C, C6C, C7C, C8C, C9C, C10C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Sof(O1C)=Sof(O2C)=Sof(H2C)=Sof(O3C)=Sof(C1C)=Sof(C2C)=Sof(H2CA)=Sof(C3C)=
 Sof(C4C)=Sof(H4C)=Sof(C5C)=Sof(H5C)=Sof(C6C)=Sof(H6C)=Sof(C7C)=Sof(C8C)=
 Sof(H8C)=Sof(C9C)=Sof(H9CA)=Sof(H9CB)=Sof(H9CC)=Sof(C10C)=1-FVAR(1)
 Sof(O1A)=Sof(O2A)=Sof(H2A)=Sof(O3A)=Sof(C1A)=Sof(C2A)=Sof(H2AA)=Sof(C3A)=
 Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(C8A)=
 Sof(H8A)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=Sof(C10A)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C8A(H8A), C8C(H8C)
7.b Aromatic/amide H refined with riding coordinates:
 C2C(H2CA), C4C(H4C), C5C(H5C), C6C(H6C), C2A(H2AA), C4A(H4A), C5A(H5A),
 C6A(H6A), C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A), C16A(H16A)
7.c Fitted hexagon refined as free rotating group:
 C1C(C2C,C3C,C4C,C5C,C6C)
7.d Idealised Me refined as rotating group:
 C9A(H9AA,H9AB,H9AC), C9C(H9CA,H9CB,H9CC)
7.e Idealised tetrahedral OH refined as rotating group:
 O2C(H2C)
;
_olex2_submission_special_instructions 'No special instructions were received'