#------------------------------------------------------------------------------
#$Date: 2020-04-21 23:19:45 +0300 (Tue, 21 Apr 2020) $
#$Revision: 250988 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038283.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_4038283
loop_
_publ_author_name
'Chen, Guo-Shu'
'Yan, Xiaoxue'
'Chen, Shujie'
'Mao, Xiang-Yu'
'Li, Zhao-Dong'
'Liu, Yunlin'
_publ_section_title
;
 Diastereoselective Synthesis of 1,3-Diyne-Tethered
 Trifluoromethyl-Cyclopropanes through Sulfur Ylides-Mediated
 Cyclopropanation/ DBU-Mediated Epimerization Sequence.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00162
_journal_year                    2020
_chemical_formula_moiety         'C15 H8 Br F3 O'
_chemical_formula_sum            'C15 H8 Br F3 O'
_chemical_formula_weight         341.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-12-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.070(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.9012(13)
_cell_length_b                   5.7981(3)
_cell_length_c                   26.3242(16)
_cell_measurement_reflns_used    3856
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      26.8440
_cell_measurement_theta_min      3.1770
_cell_volume                     2742.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            12518
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.450
_diffrn_reflns_theta_min         2.267
_exptl_absorpt_coefficient_mu    3.023
_exptl_absorpt_correction_T_max  0.717
_exptl_absorpt_correction_T_min  0.682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0367
_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)+(0.0252P)²+0.7728P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0722
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2765
_reflns_number_total             3791
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00162_si_001.cif
_cod_data_source_block           exp_1990
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4038283
_shelx_shelxl_version_number     2014/7
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C5(H5), C2(H2)
2.d :
 C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -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
Br1 Br 0.23901(2) 0.17644(4) 0.19301(2) 0.03188(9) Uani 1 1 d . . . . .
F3 F 0.61966(8) 1.2198(2) 0.17665(5) 0.0334(3) Uani 1 1 d . . . . .
F1 F 0.56175(8) 0.9837(2) 0.21256(5) 0.0381(4) Uani 1 1 d . . . . .
F2 F 0.52714(8) 1.3379(2) 0.20080(6) 0.0404(4) Uani 1 1 d . . . . .
O1 O 0.35357(8) 0.9380(2) 0.03652(6) 0.0233(3) Uani 1 1 d . . . . .
C6 C 0.33311(13) 0.5552(4) 0.19155(9) 0.0231(5) Uani 1 1 d . . . . .
H6 H 0.3505 0.5352 0.2284 0.028 Uiso 1 1 calc R . . . .
C12 C 0.52778(12) 0.9184(3) 0.09846(8) 0.0174(4) Uani 1 1 d . . . . .
C13 C 0.55262(12) 0.7646(3) 0.07906(8) 0.0183(5) Uani 1 1 d . . . . .
C3 C 0.28159(12) 0.6090(4) 0.08148(8) 0.0204(5) Uani 1 1 d . . . . .
H3 H 0.2647 0.6259 0.0445 0.024 Uiso 1 1 calc R . . . .
C8 C 0.41689(12) 1.1165(3) 0.11838(8) 0.0193(5) Uani 1 1 d . . . . .
H8 H 0.4040 1.1702 0.1497 0.023 Uiso 1 1 calc R . . . .
C7 C 0.36715(12) 0.9367(3) 0.08480(8) 0.0182(5) Uani 1 1 d . . . . .
C14 C 0.58120(12) 0.5842(4) 0.05736(8) 0.0204(5) Uani 1 1 d . . . . .
C4 C 0.33660(12) 0.7567(3) 0.11223(8) 0.0168(4) Uani 1 1 d . . . . .
C10 C 0.50033(12) 1.1007(3) 0.12458(8) 0.0175(4) Uani 1 1 d . . . . .
C1 C 0.27783(12) 0.4138(4) 0.16010(9) 0.0214(5) Uani 1 1 d . . . . .
C5 C 0.36202(13) 0.7264(4) 0.16744(8) 0.0215(5) Uani 1 1 d . . . . .
H5 H 0.3990 0.8229 0.1883 0.026 Uiso 1 1 calc R . . . .
C2 C 0.25196(12) 0.4387(4) 0.10517(9) 0.0236(5) Uani 1 1 d . . . . .
H2 H 0.2150 0.3415 0.0845 0.028 Uiso 1 1 calc R . . . .
C9 C 0.45204(13) 1.2885(3) 0.09199(9) 0.0232(5) Uani 1 1 d . . . . .
H9A H 0.4589 1.4437 0.1065 0.028 Uiso 1 1 calc R . . . .
H9B H 0.4401 1.2801 0.0534 0.028 Uiso 1 1 calc R . . . .
C11 C 0.55240(13) 1.1610(4) 0.17859(9) 0.0251(5) Uani 1 1 d . . . . .
C15 C 0.60494(13) 0.4261(4) 0.03903(9) 0.0269(5) Uani 1 1 d . . . . .
H15 H 0.6235 0.3022 0.0247 0.032 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'
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
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C1 119.0(2) . . ?
C13 C12 C10 177.0(2) . . ?
C12 C13 C14 178.9(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.79(19) . . ?
C7 C8 H8 116.4 . . ?
C7 C8 C10 117.23(17) . . ?
C10 C8 H8 116.4 . . ?
C9 C8 H8 116.4 . . ?
C9 C8 C7 118.83(18) . . ?
C9 C8 C10 59.76(14) . . ?
O1 C7 C8 120.23(19) . . ?
O1 C7 C4 121.67(18) . . ?
C4 C7 C8 118.09(18) . . ?
C15 C14 C13 178.7(2) . . ?
C3 C4 C7 118.78(18) . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 C7 122.40(19) . . ?
C12 C10 C8 120.12(17) . . ?
C12 C10 C9 120.15(18) . . ?
C12 C10 C11 113.31(18) . . ?
C9 C10 C8 58.40(14) . . ?
C11 C10 C8 115.93(18) . . ?
C11 C10 C9 118.41(18) . . ?
C6 C1 Br1 119.05(16) . . ?
C2 C1 Br1 119.55(17) . . ?
C2 C1 C6 121.4(2) . . ?
C6 C5 C4 120.9(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C8 C9 C10 61.84(14) . . ?
C8 C9 H9A 117.6 . . ?
C8 C9 H9B 117.6 . . ?
C10 C9 H9A 117.6 . . ?
C10 C9 H9B 117.6 . . ?
H9A C9 H9B 114.7 . . ?
F3 C11 F1 107.02(19) . . ?
F3 C11 F2 107.11(17) . . ?
F3 C11 C10 112.15(18) . . ?
F1 C11 F2 106.70(18) . . ?
F1 C11 C10 111.53(17) . . ?
F2 C11 C10 112.00(19) . . ?
C14 C15 H15 180.0 . . ?
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
Br1 C1 1.891(2) . ?
F3 C11 1.332(3) . ?
F1 C11 1.338(2) . ?
F2 C11 1.340(3) . ?
O1 C7 1.216(2) . ?
C6 H6 0.9300 . ?
C6 C1 1.383(3) . ?
C6 C5 1.379(3) . ?
C12 C13 1.193(3) . ?
C12 C10 1.443(3) . ?
C13 C14 1.380(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.395(3) . ?
C3 C2 1.377(3) . ?
C8 H8 0.9800 . ?
C8 C7 1.496(3) . ?
C8 C10 1.537(3) . ?
C8 C9 1.485(3) . ?
C7 C4 1.484(3) . ?
C14 C15 1.187(3) . ?
C4 C5 1.393(3) . ?
C10 C9 1.506(3) . ?
C10 C11 1.498(3) . ?
C1 C2 1.383(3) . ?
C5 H5 0.9300 . ?
C2 H2 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C15 H15 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
Br1 C1 C2 C3 -178.73(16) . . . . ?
O1 C7 C4 C3 -10.7(3) . . . . ?
O1 C7 C4 C5 167.8(2) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
C12 C10 C9 C8 108.9(2) . . . . ?
C12 C10 C11 F3 56.6(2) . . . . ?
C12 C10 C11 F1 -63.4(2) . . . . ?
C12 C10 C11 F2 177.07(17) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C8 C7 C4 C3 170.48(19) . . . . ?
C8 C7 C4 C5 -11.0(3) . . . . ?
C8 C10 C11 F3 -158.60(17) . . . . ?
C8 C10 C11 F1 81.4(2) . . . . ?
C8 C10 C11 F2 -38.1(2) . . . . ?
C7 C8 C10 C12 0.2(3) . . . . ?
C7 C8 C10 C9 109.1(2) . . . . ?
C7 C8 C10 C11 -142.09(19) . . . . ?
C7 C8 C9 C10 -106.5(2) . . . . ?
C7 C4 C5 C6 -179.1(2) . . . . ?
C4 C3 C2 C1 -0.5(3) . . . . ?
C10 C8 C7 O1 -71.6(3) . . . . ?
C10 C8 C7 C4 107.2(2) . . . . ?
C1 C6 C5 C4 -0.4(3) . . . . ?
C5 C6 C1 Br1 179.20(16) . . . . ?
C5 C6 C1 C2 1.0(3) . . . . ?
C2 C3 C4 C7 179.6(2) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C9 C8 C7 O1 -2.9(3) . . . . ?
C9 C8 C7 C4 175.92(18) . . . . ?
C9 C8 C10 C12 -109.0(2) . . . . ?
C9 C8 C10 C11 108.8(2) . . . . ?
C9 C10 C11 F3 -92.1(2) . . . . ?
C9 C10 C11 F1 147.8(2) . . . . ?
C9 C10 C11 F2 28.3(3) . . . . ?
C11 C10 C9 C8 -104.5(2) . . . . ?
