#------------------------------------------------------------------------------
#$Date: 2020-10-02 04:19:20 +0300 (Fri, 02 Oct 2020) $
#$Revision: 256905 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/92/1559238.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_1559238
loop_
_publ_author_name
'Liu, Zhong'
'Tu, Xian-Shuang'
'Guo, Le-Tao'
'Wang, Xiao-Chen'
_publ_section_title
;
 Aluminum--Catalyzed Tunable Halodefluorination of Trifluoromethyl- and
 Difluoroalkyl-Substituted Olefins
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC03883K
_journal_year                    2020
_chemical_formula_moiety         'C15 H11 Br2 F'
_chemical_formula_sum            'C15 H11 Br2 F'
_chemical_formula_weight         370.06
_chemical_properties_physical    Heat-sensitive
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2020-05-13 deposited with the CCDC.	2020-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                93.858(5)
_cell_angle_beta                 114.425(7)
_cell_angle_gamma                109.404(5)
_cell_formula_units_Z            2
_cell_length_a                   8.7495(5)
_cell_length_b                   9.7201(5)
_cell_length_c                   9.7633(7)
_cell_measurement_reflns_used    6017
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      28.6110
_cell_measurement_theta_min      3.6390
_cell_volume                     692.53(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      294.15
_diffrn_detector                 PILT
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00  94.00   1.00   30.00    --    5.00  45.00   0.00  178
  2  ω    -97.00  81.00   1.00   30.00    --   -8.10  45.00  90.00  178
  3  ω    -95.00 -69.00   1.00   30.00    --   -8.10  45.00 120.00   26
  4  ω    -97.00 -46.00   1.00   30.00    --   -8.10  45.00 150.00   51
  5  ω     56.00  81.00   1.00   30.00    --   -8.10  45.00 150.00   25
  6  ω    -96.00  25.00   1.00   30.00    --   -8.10  45.00  30.00  121
  7  ω    -15.00  45.00   1.00   30.00    --   -8.10  45.00  90.00   60
  8  ω    -51.00  80.00   1.00   30.00    --   -8.10  45.00 120.00  131
  9  ω      4.00  80.00   1.00   30.00    --   -8.10  45.00  -5.74   76
 10  ω    -70.00 -44.00   1.00   30.00    --   -8.10  45.00  -5.74   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0209536000
_diffrn_orient_matrix_UB_12      0.0136746000
_diffrn_orient_matrix_UB_13      -0.0619252000
_diffrn_orient_matrix_UB_21      -0.0685108000
_diffrn_orient_matrix_UB_22      -0.0714596000
_diffrn_orient_matrix_UB_23      -0.0462922000
_diffrn_orient_matrix_UB_31      -0.0653588000
_diffrn_orient_matrix_UB_32      0.0324432000
_diffrn_orient_matrix_UB_33      -0.0277870000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19699
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.273
_diffrn_reflns_theta_min         3.658
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.843
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.775
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.0043(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3400
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0287
_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/[σ²(Fo²)+(0.0355P)²+0.1251P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0741
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2542
_reflns_number_total             3400
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc03883k2.cif
_cod_data_source_block           m20190315a
_cod_original_cell_volume        692.53(8)
_cod_database_code               1559238
_shelx_shelxl_version_number     2018/3
_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_max   0.455
_shelx_estimated_absorpt_t_min   0.360
_reflns_odcompleteness_completeness 99.10
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C15(H15), C5(H5), C9(H9), C6(H6), C14(H14), C13(H13), C11(H11),
 C12(H12)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.330
_oxdiff_exptl_absorpt_empirical_full_min 0.434
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Br2 Br 0.93599(3) 0.72209(3) 0.22787(3) 0.05147(10) Uani 1 1 d . . . . .
Br1 Br 0.87873(4) 0.88120(3) 0.61761(3) 0.06798(12) Uani 1 1 d . . . . .
F1 F 0.7687(3) 0.59562(18) 0.63050(19) 0.0752(5) Uani 1 1 d . . . . .
C7 C 0.4886(3) 0.1291(3) 0.2269(3) 0.0429(5) Uani 1 1 d . . . . .
C2 C 0.7202(3) 0.6117(3) 0.3793(3) 0.0448(5) Uani 1 1 d . . . . .
C4 C 0.6433(3) 0.4446(3) 0.3253(3) 0.0445(5) Uani 1 1 d . . . . .
C10 C 0.4027(3) -0.0386(3) 0.1780(3) 0.0446(5) Uani 1 1 d . . . . .
C8 C 0.6577(3) 0.2044(3) 0.3562(3) 0.0474(5) Uani 1 1 d . . . . .
H8 H 0.720997 0.149548 0.410721 0.057 Uiso 1 1 calc R . . . .
C3 C 0.7278(3) 0.7046(3) 0.2657(3) 0.0470(5) Uani 1 1 d . . . . .
H3A H 0.739438 0.803780 0.305157 0.056 Uiso 1 1 calc R . . . .
H3B H 0.615250 0.658854 0.169112 0.056 Uiso 1 1 calc R . . . .
C15 C 0.4212(3) -0.1242(3) 0.2868(3) 0.0494(6) Uani 1 1 d . . . . .
H15 H 0.490478 -0.076590 0.391603 0.059 Uiso 1 1 calc R . . . .
C5 C 0.4774(3) 0.3696(3) 0.1931(3) 0.0511(6) Uani 1 1 d . . . . .
H5 H 0.416549 0.424444 0.135604 0.061 Uiso 1 1 calc R . . . .
C9 C 0.7338(3) 0.3593(3) 0.4055(3) 0.0476(5) Uani 1 1 d . . . . .
H9 H 0.846527 0.406898 0.493188 0.057 Uiso 1 1 calc R . . . .
C6 C 0.4014(3) 0.2154(3) 0.1457(3) 0.0516(6) Uani 1 1 d . . . . .
H6 H 0.289181 0.167964 0.057470 0.062 Uiso 1 1 calc R . . . .
C14 C 0.3385(4) -0.2794(3) 0.2425(3) 0.0552(6) Uani 1 1 d . . . . .
H14 H 0.352165 -0.335095 0.317282 0.066 Uiso 1 1 calc R . . . .
C1 C 0.7784(4) 0.6755(3) 0.5259(3) 0.0527(6) Uani 1 1 d . . . . .
C13 C 0.2367(3) -0.3508(3) 0.0891(4) 0.0607(7) Uani 1 1 d . . . . .
H13 H 0.180561 -0.455114 0.059707 0.073 Uiso 1 1 calc R . . . .
C11 C 0.2987(4) -0.1131(3) 0.0217(3) 0.0607(7) Uani 1 1 d . . . . .
H11 H 0.283837 -0.058082 -0.053761 0.073 Uiso 1 1 calc R . . . .
C12 C 0.2169(4) -0.2692(4) -0.0219(4) 0.0698(8) Uani 1 1 d . . . . .
H12 H 0.148927 -0.318360 -0.126331 0.084 Uiso 1 1 calc R . . . .
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'
Br Br -0.2901 2.4595 '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'
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
C8 C7 C10 121.3(2) . . ?
C8 C7 C6 117.5(2) . . ?
C6 C7 C10 121.2(2) . . ?
C3 C2 C4 118.9(2) . . ?
C1 C2 C4 120.4(2) . . ?
C1 C2 C3 120.7(2) . . ?
C5 C4 C2 120.5(2) . . ?
C5 C4 C9 117.9(2) . . ?
C9 C4 C2 121.6(2) . . ?
C15 C10 C7 120.8(2) . . ?
C15 C10 C11 118.2(2) . . ?
C11 C10 C7 121.0(2) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.4(2) . . ?
C9 C8 H8 119.3 . . ?
Br2 C3 H3A 109.6 . . ?
Br2 C3 H3B 109.6 . . ?
C2 C3 Br2 110.39(16) . . ?
C2 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.1(2) . . ?
C14 C15 H15 119.4 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C9 H9 119.7 . . ?
C8 C9 C4 120.7(2) . . ?
C8 C9 H9 119.7 . . ?
C7 C6 H6 119.3 . . ?
C5 C6 C7 121.4(2) . . ?
C5 C6 H6 119.3 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.1(3) . . ?
C13 C14 H14 120.0 . . ?
F1 C1 Br1 110.05(17) . . ?
C2 C1 Br1 127.4(2) . . ?
C2 C1 F1 122.5(2) . . ?
C14 C13 H13 119.9 . . ?
C14 C13 C12 120.3(3) . . ?
C12 C13 H13 119.9 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 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
Br2 C3 1.960(2) . ?
Br1 C1 1.874(2) . ?
F1 C1 1.337(3) . ?
C7 C10 1.494(3) . ?
C7 C8 1.389(3) . ?
C7 C6 1.389(3) . ?
C2 C4 1.494(3) . ?
C2 C3 1.485(3) . ?
C2 C1 1.327(4) . ?
C4 C5 1.387(3) . ?
C4 C9 1.393(3) . ?
C10 C15 1.384(3) . ?
C10 C11 1.395(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.383(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C15 H15 0.9300 . ?
C15 C14 1.383(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(4) . ?
C9 H9 0.9300 . ?
C6 H6 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.366(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.373(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.392(4) . ?
C12 H12 0.9300 . ?
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
C7 C10 C15 C14 178.5(2) . . . . ?
C7 C10 C11 C12 -178.9(3) . . . . ?
C7 C8 C9 C4 -0.8(4) . . . . ?
C2 C4 C5 C6 -177.3(2) . . . . ?
C2 C4 C9 C8 178.1(2) . . . . ?
C4 C2 C3 Br2 -78.8(2) . . . . ?
C4 C2 C1 Br1 -179.93(18) . . . . ?
C4 C2 C1 F1 -1.2(4) . . . . ?
C4 C5 C6 C7 -0.9(4) . . . . ?
C10 C7 C8 C9 -177.2(2) . . . . ?
C10 C7 C6 C5 178.0(2) . . . . ?
C10 C15 C14 C13 0.2(4) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C8 C7 C10 C15 36.3(3) . . . . ?
C8 C7 C10 C11 -145.0(3) . . . . ?
C8 C7 C6 C5 -1.3(4) . . . . ?
C3 C2 C4 C5 -48.6(3) . . . . ?
C3 C2 C4 C9 131.9(2) . . . . ?
C3 C2 C1 Br1 -0.8(4) . . . . ?
C3 C2 C1 F1 177.9(2) . . . . ?
C15 C10 C11 C12 -0.2(4) . . . . ?
C15 C14 C13 C12 0.4(4) . . . . ?
C5 C4 C9 C8 -1.4(4) . . . . ?
C9 C4 C5 C6 2.2(4) . . . . ?
C6 C7 C10 C15 -142.9(3) . . . . ?
C6 C7 C10 C11 35.8(4) . . . . ?
C6 C7 C8 C9 2.1(4) . . . . ?
C14 C13 C12 C11 -0.9(4) . . . . ?
C1 C2 C4 C5 130.5(3) . . . . ?
C1 C2 C4 C9 -49.0(4) . . . . ?
C1 C2 C3 Br2 102.1(2) . . . . ?
C11 C10 C15 C14 -0.3(4) . . . . ?
