#------------------------------------------------------------------------------
#$Date: 2021-06-05 20:18:06 +0300 (Sat, 05 Jun 2021) $
#$Revision: 265843 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/81/7128114.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7128114
loop_
_publ_author_name
'Wu, Qiuzi'
'Mao, Yang-Jie'
'Zhou, Kun'
'Wang, Shuang'
'Chen, Lei'
'Xu, Zhen-Yuan'
'Lou, Shao-Jie'
'Xu, Dan-Qian'
_publ_section_title
;
 Pd-Catalysed direct C(sp²)-H fluorination of aromatic ketones:
 concise access to anacetrapib.
;
_journal_issue                   37
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4544
_journal_page_last               4547
_journal_paper_doi               10.1039/d1cc01047f
_journal_volume                  57
_journal_year                    2021
_chemical_formula_sum            'C15 H13 F O2'
_chemical_formula_weight         244.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2020-08-04 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2060(8)
_cell_length_b                   6.9192(6)
_cell_length_c                   22.420(2)
_cell_measurement_reflns_used    2322
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      53.438
_cell_measurement_theta_min      5.386
_cell_volume                     1273.0(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      190(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6041
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.987
_diffrn_reflns_theta_min         2.643
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.088(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0688P)²+0.1439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1351
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1007
_reflns_number_total             1348
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc01047f2.cif
_cod_data_source_block           d8v18818
_cod_depositor_comments
'Adding full bibliography for 7128113--7128114.cif.'
_cod_database_code               7128114
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.988
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.36278(17) 0.7500 0.60585(6) 0.0837(6) Uani 1 2 d S T P . .
O1 O 0.8480(2) 0.7500 0.55436(8) 0.0804(6) Uani 1 2 d S T P . .
O2 O 0.20455(17) 0.7500 0.40304(6) 0.0616(5) Uani 1 2 d S T P . .
C1 C 0.4062(3) 0.7500 0.54751(9) 0.0549(6) Uani 1 2 d S T P . .
C2 C 0.2796(2) 0.7500 0.50755(9) 0.0547(6) Uani 1 2 d S T P . .
H2 H 0.1696 0.7500 0.5207 0.066 Uiso 1 2 calc R U P . .
C3 C 0.3174(2) 0.7500 0.44739(9) 0.0514(5) Uani 1 2 d S T P . .
C4 C 0.4791(2) 0.7500 0.42911(9) 0.0554(6) Uani 1 2 d S T P . .
H4 H 0.5054 0.7500 0.3878 0.067 Uiso 1 2 calc R U P . .
C5 C 0.6000(3) 0.7500 0.47097(9) 0.0557(6) Uani 1 2 d S T P . .
H5 H 0.7101 0.7500 0.4578 0.067 Uiso 1 2 calc R U P . .
C6 C 0.5691(2) 0.7500 0.53241(9) 0.0518(5) Uani 1 2 d S T P . .
C7 C 0.7102(3) 0.7500 0.57407(11) 0.0612(6) Uani 1 2 d S T P . .
C8 C 0.6843(5) 0.7500 0.63989(13) 0.0881(9) Uani 1 2 d S T P . .
C9 C 0.0360(3) 0.7500 0.42026(9) 0.0638(6) Uani 1 2 d S T P . .
H9A H 0.0113 0.8661 0.4444 0.077 Uiso 0.5 1 calc R U P . .
H9B H 0.0113 0.6339 0.4444 0.077 Uiso 0.5 1 calc R U P . .
C10 C -0.0638(3) 0.7500 0.36473(10) 0.0623(6) Uani 1 2 d S T P . .
C11 C -0.1110(3) 0.5788(3) 0.33912(9) 0.0877(6) Uani 1 1 d . . . . .
H11 H -0.0804 0.4595 0.3568 0.105 Uiso 1 1 calc R U . . .
C12 C -0.2026(3) 0.5801(5) 0.28777(12) 0.1248(11) Uani 1 1 d . . . . .
H12 H -0.2357 0.4614 0.2702 0.150 Uiso 1 1 calc R U . . .
C13 C -0.2462(5) 0.7500 0.26205(16) 0.1344(17) Uani 1 2 d S T P . .
H13 H -0.3071 0.7500 0.2260 0.161 Uiso 1 2 calc R U P . .
H8A H 0.785(5) 0.7500 0.6579(15) 0.115(11) Uiso 1 2 d S . P . .
H8B H 0.619(3) 0.863(3) 0.6516(10) 0.114(8) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 C9 117.38(16) . . ?
F1 C1 C2 115.51(18) . . ?
F1 C1 C6 119.47(19) . . ?
C2 C1 C6 125.0(2) . . ?
C1 C2 C3 117.79(19) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
O2 C3 C2 124.05(18) . . ?
O2 C3 C4 115.81(17) . . ?
C2 C3 C4 120.13(19) . . ?
C5 C4 C3 119.43(19) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 122.96(19) . . ?
C4 C5 H5 118.5 . . ?
C6 C5 H5 118.5 . . ?
C1 C6 C5 114.66(19) . . ?
C1 C6 C7 126.9(2) . . ?
C5 C6 C7 118.44(19) . . ?
O1 C7 C6 119.8(2) . . ?
O1 C7 C8 119.6(2) . . ?
C6 C7 C8 120.7(2) . . ?
C7 C8 H8A 108(2) . . ?
C7 C8 H8B 110.0(13) . . ?
H8A C8 H8B 111.9(18) . . ?
O2 C9 C10 107.75(17) . . ?
O2 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
O2 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C11 C10 C11 119.4(3) 7_575 . ?
C11 C10 C9 120.31(13) 7_575 . ?
C11 C10 C9 120.32(13) . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C12 120.0(3) 7_575 . ?
C12 C13 H13 120.0 7_575 . ?
C12 C13 H13 120.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.356(2) . ?
O1 C7 1.213(3) . ?
O2 C3 1.359(2) . ?
O2 C9 1.436(3) . ?
C1 C2 1.372(3) . ?
C1 C6 1.379(3) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(3) . ?
C4 C5 1.366(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.401(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.488(3) . ?
C7 C8 1.491(4) . ?
C8 H8A 0.92(4) . ?
C8 H8B 0.98(2) . ?
C9 C10 1.490(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.372(2) 7_575 ?
C10 C11 1.372(2) . ?
C11 C12 1.375(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.358(3) . ?
C12 H12 0.9500 . ?
C13 C12 1.357(3) 7_575 ?
C13 H13 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C3 180.000(1) . . . . ?
C6 C1 C2 C3 0.000(1) . . . . ?
C9 O2 C3 C2 0.000(1) . . . . ?
C9 O2 C3 C4 180.000(0) . . . . ?
C1 C2 C3 O2 180.000(1) . . . . ?
C1 C2 C3 C4 0.000(1) . . . . ?
O2 C3 C4 C5 180.000(1) . . . . ?
C2 C3 C4 C5 0.000(1) . . . . ?
C3 C4 C5 C6 0.000(1) . . . . ?
F1 C1 C6 C5 180.000(1) . . . . ?
C2 C1 C6 C5 0.000(1) . . . . ?
F1 C1 C6 C7 0.000(1) . . . . ?
C2 C1 C6 C7 180.000(1) . . . . ?
C4 C5 C6 C1 0.000(1) . . . . ?
C4 C5 C6 C7 180.000(1) . . . . ?
C1 C6 C7 O1 180.000(1) . . . . ?
C5 C6 C7 O1 0.000(1) . . . . ?
C1 C6 C7 C8 0.000(1) . . . . ?
C5 C6 C7 C8 180.000(1) . . . . ?
C3 O2 C9 C10 180.000(0) . . . . ?
O2 C9 C10 C11 -90.38(18) . . . 7_575 ?
O2 C9 C10 C11 90.38(18) . . . . ?
C11 C10 C11 C12 1.0(4) 7_575 . . . ?
C9 C10 C11 C12 -179.8(2) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 C12 C13 C12 -1.6(6) . . . 7_575 ?
