Crystal structure of 4-(3-fluorophenyl)-7-hydroxy-2H-chromen-2-one, C15H9FO3
Mzozoyana, Vuyisa; Zamisa, Sizwe J.; Zeitschrift für Kristallographie - New Crystal Structures 235 (2020) 631–633; doi:10.1515/ncrs-2019-0869

data_8105241
_publ_section_title
;
 Crystal structure of 4-(3-fluorophenyl)-7-hydroxy-2H-chromen-2-one,
 C15H9FO3
;
_journal_issue                   3
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              631
_journal_page_last               633
_journal_paper_doi               10.1515/ncrs-2019-0869
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         '2(C7.5 H4.5 F0.5 O1.5)'
_chemical_formula_sum            'C15 H9 F O3'
_chemical_formula_weight         256.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 104.4340(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.3523(17)
_cell_length_b                   11.2575(9)
_cell_length_c                   10.1604(8)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      3.12
_cell_volume                     2254.4(3)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2016/6 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17738
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.146
_diffrn_reflns_theta_min         1.033
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0503 before and 0.0380 after correction. The Ratio of minimum to maximum transmission is 0.9301. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         4955
_refine_ls_number_restraints     122
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0501P)^2^+0.7234P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0961
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4536
_reflns_number_total             4955
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2019-0869_suppl.cif
_cod_data_source_block           3FPhCur
_cod_database_code               8105241
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.2158(11)
 0.7842(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
3. Restrained distances
 F1B-C14C \\sim F2B-C12D
 with sigma of 0.02
 C10B-C11C \\sim C10B-C15D
 with sigma of 0.02
 C10B-C15C \\sim C10B-C11D
 with sigma of 0.02
 C11C-C12C \\sim C15D-C14D
 with sigma of 0.02
 C13C-C14C \\sim C13D-C12D
 with sigma of 0.02
 C13C-C12C \\sim C13D-C14D
 with sigma of 0.02
 C15C-C14C \\sim C11D-C12D
 with sigma of 0.02
 F1B-C13C \\sim F2B-C13D
 with sigma of 0.04
 F1B-C15C \\sim F2B-C11D
 with sigma of 0.04
 C10B-C14C \\sim C10B-C12D
 with sigma of 0.04
 C10B-C12C \\sim C10B-C14D
 with sigma of 0.04
 C11C-C13C \\sim C15D-C13D
 with sigma of 0.04
 C13C-C15C \\sim C13D-C11D
 with sigma of 0.04
 C14C-C12C \\sim C12D-C14D
 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
Uanis(C15D) \\sim Ueq, Uanis(C13D) \\sim Ueq, Uanis(C14D) \\sim Ueq,
Uanis(C12D) \\sim Ueq, Uanis(C11D) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(C10A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(F2B) \\sim Ueq, Uanis(F1B) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
5. Rigid body (RIGU) restrains
 H14D, H15D, H13D, F2B, C14D, C11D, C13D, H11D, C12D, C15D
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 H13C, H12C, C15C, F1B, C13C, C11C, C14C, H11C, H15C, C12C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(F2B)=Sof(C11D)=Sof(H11D)=Sof(C15D)=Sof(H15D)=Sof(C14D)=Sof(H14D)=
 Sof(C13D)=Sof(H13D)=Sof(C12D)=1-FVAR(1)
 Sof(F1B)=Sof(C11C)=Sof(H11C)=Sof(C12C)=Sof(H12C)=Sof(C13C)=Sof(H13C)=
 Sof(C14C)=Sof(C15C)=Sof(H15C)=FVAR(1)
7.a Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C5(H5), C5A(H5A), C8A(H8A), C11A(H11A), C12A(H12A), C13A(H13A),
 C15A(H15A), C2B(H2B), C3B(H3B), C5B(H5B), C8B(H8B), C11C(H11C), C12C(H12C),
 C13C(H13C), C15C(H15C), C11D(H11D), C15D(H15D), C14D(H14D), C13D(H13D)
7.b Fitted hexagon refined as free rotating group:
 C11D(C10B,C15D,C14D,C13D,C12D)
7.c Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1B(H1B)
;