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#$Date: 2024-01-06 09:22:59 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288744 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/03/1570330.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_1570330
loop_
_publ_author_name
'Stünkel, Timo'
'Siebold, Kathrin'
'Okumatsu, Daichi'
'Murata, Kazuki'
'Ruyet, Louise'
'Daniliuc, Constantin G.'
'Gilmour, Ryan'
_publ_section_title
;
 para-Selective dearomatization of phenols by I(i)/I(iii)
 catalysis-based fluorination.
;
_journal_issue                   46
_journal_name_full               'Chemical science'
_journal_page_first              13574
_journal_page_last               13580
_journal_paper_doi               10.1039/d3sc05952a
_journal_volume                  14
_journal_year                    2023
_chemical_formula_sum            'C8 H10 Br F O2'
_chemical_formula_weight         237.07
_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
_atom_sites_solution_primary     direct
_audit_creation_method           'APEX4 v2021.4-0'
_audit_update_record
;
2023-08-16 deposited with the CCDC.	2023-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.677(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6997(4)
_cell_length_b                   15.8634(8)
_cell_length_c                   6.6702(4)
_cell_measurement_reflns_used    8485
_cell_measurement_temperature    101.(2)
_cell_measurement_theta_max      66.5201
_cell_measurement_theta_min      5.2113
_cell_volume                     898.09(8)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker APEX4 v2021.4-0 Photon III'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1242)'
_computing_publication_material  'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      101.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            12842
_diffrn_reflns_theta_full        66.91
_diffrn_reflns_theta_max         66.91
_diffrn_reflns_theta_min         5.58
_diffrn_source                   'Cu ImS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'micro focus tube'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    6.071
_exptl_absorpt_correction_T_max  0.70
_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.342
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.373
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0310
_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)+(0.0131P)²+2.3775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0714
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1421
_reflns_number_total             1569
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc05952a2.cif
_cod_data_source_block           gil10452_30
_cod_depositor_comments
'Adding full bibliography for 1570328--1570331.cif.'
_cod_database_code               1570330
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.42540(4) 0.66949(2) 0.57491(6) 0.03324(14) Uani d . . . 1 . .
C C1 0.2812(4) 0.50787(19) 0.6016(5) 0.0226(7) Uani d . . . 1 . .
C C2 0.3964(4) 0.5691(2) 0.7329(5) 0.0250(7) Uani d . . . 1 . .
H H2 0.500544 0.540210 0.776367 0.030000 Uiso calc U . R 1 . .
C C3 0.3341(4) 0.58628(19) 0.9205(5) 0.0239(7) Uani d . . . 1 . .
H H3 0.408331 0.604071 1.050186 0.029000 Uiso calc U . R 1 . .
C C4 0.2092(3) 0.51725(19) 0.9292(5) 0.0212(6) Uani d . . . 1 . .
H H4 0.204620 0.491426 1.064492 0.025000 Uiso calc U . R 1 . .
C C5 0.1927(4) 0.46148(18) 0.7425(4) 0.0213(6) Uani d . . . 1 . .
H H5 0.079796 0.451778 0.674321 0.026000 Uiso calc U . R 1 . .
C C6 0.1628(4) 0.6073(2) 0.8895(5) 0.0231(7) Uani d . . . 1 . .
C C7 0.0993(4) 0.6590(2) 1.0395(5) 0.0281(7) Uani d . . . 1 . .
H H7A 0.152499 0.643247 1.179654 0.042000 Uiso calc U . R 1 . .
H H7B -0.014083 0.648927 1.020400 0.042000 Uiso calc U . R 1 . .
H H7C 0.117908 0.718876 1.017195 0.042000 Uiso calc U . R 1 . .
C C8 0.2244(4) 0.3176(2) 0.6619(5) 0.0276(7) Uani d . . . 1 . .
H H8A 0.112942 0.304787 0.653289 0.041000 Uiso calc U . R 1 . .
H H8B 0.287937 0.267257 0.706801 0.041000 Uiso calc U . R 1 . .
H H8C 0.239199 0.335103 0.526475 0.041000 Uiso calc U . R 1 . .
F F1 0.08636(19) 0.62537(11) 0.6874(3) 0.0255(4) Uani d . . . 1 . .
O O1 0.2664(3) 0.49556(15) 0.4200(3) 0.0330(5) Uani d . . . 1 . .
O O2 0.2729(2) 0.38440(13) 0.8068(3) 0.0231(5) Uani d . . . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C2 . . 126.3(3) ?
O1 C1 C5 . . 125.7(3) ?
C2 C1 C5 . . 108.0(2) ?
C3 C2 C1 . . 106.5(3) ?
C3 C2 Br1 . . 114.6(2) ?
C1 C2 Br1 . . 110.8(2) ?
C3 C2 H2 . . 108.300000 ?
C1 C2 H2 . . 108.300000 ?
Br1 C2 H2 . . 108.300000 ?
C2 C3 C6 . . 117.3(3) ?
C2 C3 C4 . . 106.7(3) ?
C6 C3 C4 . . 58.6(2) ?
C2 C3 H3 . . 119.400000 ?
C6 C3 H3 . . 119.400000 ?
C4 C3 H3 . . 119.400000 ?
C6 C4 C5 . . 116.2(3) ?
C6 C4 C3 . . 58.8(2) ?
C5 C4 C3 . . 108.9(3) ?
C6 C4 H4 . . 119.300000 ?
C5 C4 H4 . . 119.300000 ?
C3 C4 H4 . . 119.300000 ?
O2 C5 C4 . . 107.6(2) ?
O2 C5 C1 . . 108.6(2) ?
C4 C5 C1 . . 104.8(2) ?
O2 C5 H5 . . 111.800000 ?
C4 C5 H5 . . 111.800000 ?
C1 C5 H5 . . 111.800000 ?
F1 C6 C7 . . 111.6(3) ?
F1 C6 C4 . . 114.9(3) ?
C7 C6 C4 . . 122.2(3) ?
F1 C6 C3 . . 115.3(3) ?
C7 C6 C3 . . 122.3(3) ?
C4 C6 C3 . . 62.6(2) ?
C6 C7 H7A . . 109.500000 ?
C6 C7 H7B . . 109.500000 ?
H7A C7 H7B . . 109.500000 ?
C6 C7 H7C . . 109.500000 ?
H7A C7 H7C . . 109.500000 ?
H7B C7 H7C . . 109.500000 ?
O2 C8 H8A . . 109.500000 ?
O2 C8 H8B . . 109.500000 ?
H8A C8 H8B . . 109.500000 ?
O2 C8 H8C . . 109.500000 ?
H8A C8 H8C . . 109.500000 ?
H8B C8 H8C . . 109.500000 ?
C5 O2 C8 . . 112.3(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C2 . 1.956(3) ?
C1 O1 . 1.205(4) ?
C1 C2 . 1.527(4) ?
C1 C5 . 1.528(4) ?
C2 C3 . 1.494(5) ?
C2 H2 . 1.000000 ?
C3 C6 . 1.497(4) ?
C3 C4 . 1.552(4) ?
C3 H3 . 1.000000 ?
C4 C6 . 1.493(4) ?
C4 C5 . 1.508(4) ?
C4 H4 . 1.000000 ?
C5 O2 . 1.426(3) ?
C5 H5 . 1.000000 ?
C6 F1 . 1.395(3) ?
C6 C7 . 1.490(5) ?
C7 H7A . 0.980000 ?
C7 H7B . 0.980000 ?
C7 H7C . 0.980000 ?
C8 O2 . 1.434(4) ?
C8 H8A . 0.980000 ?
C8 H8B . 0.980000 ?
C8 H8C . 0.980000 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . 159.7(3) ?
C5 C1 C2 C3 . . . . -23.0(3) ?
O1 C1 C2 Br1 . . . . 34.4(4) ?
C5 C1 C2 Br1 . . . . -148.2(2) ?
C1 C2 C3 C6 . . . . -47.5(3) ?
Br1 C2 C3 C6 . . . . 75.3(3) ?
C1 C2 C3 C4 . . . . 15.3(3) ?
Br1 C2 C3 C4 . . . . 138.1(2) ?
C2 C3 C4 C6 . . . . -112.2(3) ?
C2 C3 C4 C5 . . . . -2.3(3) ?
C6 C3 C4 C5 . . . . 109.8(3) ?
C6 C4 C5 O2 . . . . 167.8(2) ?
C3 C4 C5 O2 . . . . 104.0(3) ?
C6 C4 C5 C1 . . . . 52.3(3) ?
C3 C4 C5 C1 . . . . -11.5(3) ?
O1 C1 C5 O2 . . . . 83.6(4) ?
C2 C1 C5 O2 . . . . -93.7(3) ?
O1 C1 C5 C4 . . . . -161.5(3) ?
C2 C1 C5 C4 . . . . 21.1(3) ?
C5 C4 C6 F1 . . . . 9.8(4) ?
C3 C4 C6 F1 . . . . 106.9(3) ?
C5 C4 C6 C7 . . . . 150.3(3) ?
C3 C4 C6 C7 . . . . -112.6(3) ?
C5 C4 C6 C3 . . . . -97.1(3) ?
C2 C3 C6 F1 . . . . -12.4(4) ?
C4 C3 C6 F1 . . . . -106.2(3) ?
C2 C3 C6 C7 . . . . -153.8(3) ?
C4 C3 C6 C7 . . . . 112.5(3) ?
C2 C3 C6 C4 . . . . 93.7(3) ?
C4 C5 O2 C8 . . . . 161.4(2) ?
C1 C5 O2 C8 . . . . -85.6(3) ?
