#------------------------------------------------------------------------------
#$Date: 2020-10-04 06:37:09 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257139 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/87/4038757.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_4038757
loop_
_publ_author_name
'Zhang, Lili'
'Deng, Kezuan'
'Wu, Gaorong'
'Yang, Jinyue'
'Tang, Shibiao'
'Fu, Xiaopan'
'Xia, Chengcai'
'Ji, Yafei'
_publ_section_title
;
 Ruthenium(II)-Catalyzed α-Fluoroalkenylation of Oxime Ethers with
 gem-Difluorostyrenes via C-H Activation and C-F Cleavage.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12670
_journal_page_last               12681
_journal_paper_doi               10.1021/acs.joc.0c01842
_journal_volume                  85
_journal_year                    2020
_chemical_formula_sum            'C18 H17 Br F N O2'
_chemical_formula_weight         378.23
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                78.408(2)
_cell_angle_beta                 89.070(2)
_cell_angle_gamma                86.152(2)
_cell_formula_units_Z            2
_cell_length_a                   6.8494(4)
_cell_length_b                   10.5416(7)
_cell_length_c                   11.8942(8)
_cell_measurement_reflns_used    9837
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.887
_cell_measurement_theta_min      4.723
_cell_volume                     839.39(9)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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  0.0477
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20510
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.990
_diffrn_reflns_theta_min         2.362
_exptl_absorpt_coefficient_mu    2.467
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0317
_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)+(0.0513P)²+0.2265P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0905
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2817
_reflns_number_total             3284
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01842_si_001.cif
_cod_data_source_block           mo_d8v20271_0m
_cod_depositor_comments          'Adding full bibliography for 4038757.cif.'
_cod_database_code               4038757
_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   0.694
_shelx_estimated_absorpt_t_max   0.773
_shelxl_version_number           2013-4
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
Br1 Br -0.29112(4) 0.03942(3) 0.72108(2) 0.05858(13) Uani 1 1 d . . . . .
F1 F 0.2673(2) 0.49004(14) 0.38832(14) 0.0600(4) Uani 1 1 d . . . . .
O1 O 0.5910(2) 0.10216(15) 0.09670(15) 0.0469(4) Uani 1 1 d . . . . .
O2 O 1.0601(3) 0.59079(17) 0.12151(15) 0.0534(4) Uani 1 1 d . . . . .
N1 N 0.6798(3) 0.18918(18) 0.15379(16) 0.0395(4) Uani 1 1 d . . . . .
C1 C 0.0109(3) 0.2832(2) 0.4706(2) 0.0448(5) Uani 1 1 d . . . . .
H1 H -0.0156 0.3623 0.4208 0.054 Uiso 1 1 calc R U . . .
C2 C -0.1347(3) 0.2290(2) 0.5436(2) 0.0467(5) Uani 1 1 d . . . . .
H2 H -0.2587 0.2712 0.5422 0.056 Uiso 1 1 calc R U . . .
C3 C -0.0946(3) 0.1124(2) 0.61803(19) 0.0421(5) Uani 1 1 d . . . . .
C4 C 0.0865(4) 0.0464(2) 0.6195(2) 0.0428(5) Uani 1 1 d . . . . .
H4 H 0.1119 -0.0330 0.6691 0.051 Uiso 1 1 calc R U . . .
C5 C 0.2293(3) 0.1013(2) 0.5455(2) 0.0420(5) Uani 1 1 d . . . . .
H5 H 0.3514 0.0570 0.5453 0.050 Uiso 1 1 calc R U . . .
C6 C 0.1964(3) 0.2204(2) 0.47124(18) 0.0378(5) Uani 1 1 d . . . . .
C7 C 0.3586(3) 0.2734(2) 0.3981(2) 0.0425(5) Uani 1 1 d . . . . .
H7 H 0.4492 0.2125 0.3771 0.051 Uiso 1 1 calc R U . . .
C8 C 0.3926(3) 0.3962(2) 0.35823(19) 0.0401(5) Uani 1 1 d . . . . .
C9 C 0.5589(3) 0.4506(2) 0.29060(19) 0.0384(5) Uani 1 1 d . . . . .
C10 C 0.6398(4) 0.5594(2) 0.3169(2) 0.0441(5) Uani 1 1 d . . . . .
H10 H 0.5797 0.5990 0.3728 0.053 Uiso 1 1 calc R U . . .
C11 C 0.8045(4) 0.6100(2) 0.2634(2) 0.0438(5) Uani 1 1 d . . . . .
H11 H 0.8540 0.6829 0.2825 0.053 Uiso 1 1 calc R U . . .
C12 C 0.8965(3) 0.5515(2) 0.18054(19) 0.0402(5) Uani 1 1 d . . . . .
C13 C 0.8177(3) 0.4435(2) 0.15187(18) 0.0390(5) Uani 1 1 d . . . . .
H13 H 0.8800 0.4041 0.0965 0.047 Uiso 1 1 calc R U . . .
C14 C 0.6497(3) 0.3937(2) 0.20356(18) 0.0352(4) Uani 1 1 d . . . . .
C15 C 0.5636(3) 0.2885(2) 0.15691(18) 0.0366(5) Uani 1 1 d . . . . .
C16 C 0.3625(4) 0.3112(3) 0.1062(2) 0.0536(6) Uani 1 1 d . . . . .
H16A H 0.3716 0.3204 0.0243 0.080 Uiso 1 1 calc R U . . .
H16B H 0.3003 0.3889 0.1244 0.080 Uiso 1 1 calc R U . . .
H16C H 0.2867 0.2389 0.1372 0.080 Uiso 1 1 calc R U . . .
C17 C 0.7280(4) -0.0040(3) 0.0904(3) 0.0587(7) Uani 1 1 d . . . . .
H17A H 0.6806 -0.0535 0.0383 0.088 Uiso 1 1 calc R U . . .
H17B H 0.7441 -0.0583 0.1652 0.088 Uiso 1 1 calc R U . . .
H17C H 0.8516 0.0284 0.0635 0.088 Uiso 1 1 calc R U . . .
C18 C 1.1455(4) 0.7034(3) 0.1438(3) 0.0578(7) Uani 1 1 d . . . . .
H18A H 1.2609 0.7191 0.0975 0.087 Uiso 1 1 calc R U . . .
H18B H 1.1798 0.6897 0.2235 0.087 Uiso 1 1 calc R U . . .
H18C H 1.0531 0.7771 0.1254 0.087 Uiso 1 1 calc R U . . .
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'
N N 0.0061 0.0033 '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
N1 O1 C17 108.81(18) . . ?
C12 O2 C18 118.29(18) . . ?
C15 N1 O1 110.56(18) . . ?
C2 C1 C6 120.7(2) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 Br1 119.88(18) . . ?
C4 C3 Br1 118.84(18) . . ?
C3 C4 C5 118.4(2) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C6 122.1(2) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C1 117.9(2) . . ?
C5 C6 C7 118.5(2) . . ?
C1 C6 C7 123.6(2) . . ?
C8 C7 C6 128.5(2) . . ?
C8 C7 H7 115.8 . . ?
C6 C7 H7 115.8 . . ?
C7 C8 F1 118.5(2) . . ?
C7 C8 C9 129.1(2) . . ?
F1 C8 C9 112.23(19) . . ?
C10 C9 C14 117.9(2) . . ?
C10 C9 C8 119.07(19) . . ?
C14 C9 C8 122.9(2) . . ?
C11 C10 C9 122.5(2) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C10 C11 C12 119.4(2) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
O2 C12 C11 125.5(2) . . ?
O2 C12 C13 115.19(19) . . ?
C11 C12 C13 119.3(2) . . ?
C14 C13 C12 121.70(19) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C9 119.2(2) . . ?
C13 C14 C15 117.51(18) . . ?
C9 C14 C15 123.1(2) . . ?
N1 C15 C14 115.19(19) . . ?
N1 C15 C16 124.9(2) . . ?
C14 C15 C16 119.49(19) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
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 C3 1.901(2) . ?
F1 C8 1.364(3) . ?
O1 N1 1.418(2) . ?
O1 C17 1.424(3) . ?
O2 C12 1.357(3) . ?
O2 C18 1.431(3) . ?
N1 C15 1.279(3) . ?
C1 C2 1.387(3) . ?
C1 C6 1.392(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(3) . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.469(3) . ?
C7 C8 1.322(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.465(3) . ?
C9 C10 1.398(3) . ?
C9 C14 1.413(3) . ?
C10 C11 1.373(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.395(3) . ?
C13 C14 1.381(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.493(3) . ?
C15 C16 1.498(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C18 H18B F1 0.96 2.62 3.378(3) 136.6 1_655
C17 H17A O1 0.96 2.62 3.491(3) 151.2 2_655
C16 H16C Br1 0.96 3.07 3.909(3) 146.3 2_556
C16 H16B O2 0.96 2.60 3.521(3) 161.8 1_455
C13 H13 O2 0.93 2.61 3.428(3) 147.1 2_765
C13 H13 O2 0.93 2.61 3.428(3) 147.1 2_765
C16 H16B O2 0.96 2.60 3.521(3) 161.8 1_455
C16 H16C Br1 0.96 3.07 3.909(3) 146.3 2_556
C17 H17A O1 0.96 2.62 3.491(3) 151.2 2_655
C18 H18B F1 0.96 2.62 3.378(3) 136.6 1_655
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
C17 O1 N1 C15 177.4(2) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
C1 C2 C3 C4 -1.7(4) . . . . ?
C1 C2 C3 Br1 178.40(17) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
Br1 C3 C4 C5 -179.02(17) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C4 C5 C6 C1 -1.8(3) . . . . ?
C4 C5 C6 C7 178.1(2) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
C2 C1 C6 C7 -178.7(2) . . . . ?
C5 C6 C7 C8 -150.3(3) . . . . ?
C1 C6 C7 C8 29.6(4) . . . . ?
C6 C7 C8 F1 1.5(4) . . . . ?
C6 C7 C8 C9 176.3(2) . . . . ?
C7 C8 C9 C10 -138.2(3) . . . . ?
F1 C8 C9 C10 36.8(3) . . . . ?
C7 C8 C9 C14 38.0(4) . . . . ?
F1 C8 C9 C14 -147.0(2) . . . . ?
C14 C9 C10 C11 -1.5(4) . . . . ?
C8 C9 C10 C11 175.0(2) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C18 O2 C12 C11 -1.2(4) . . . . ?
C18 O2 C12 C13 178.1(2) . . . . ?
C10 C11 C12 O2 -179.7(2) . . . . ?
C10 C11 C12 C13 1.1(4) . . . . ?
O2 C12 C13 C14 -179.0(2) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C13 C14 C9 -2.3(3) . . . . ?
C12 C13 C14 C15 172.6(2) . . . . ?
C10 C9 C14 C13 2.8(3) . . . . ?
C8 C9 C14 C13 -173.5(2) . . . . ?
C10 C9 C14 C15 -171.8(2) . . . . ?
C8 C9 C14 C15 11.9(3) . . . . ?
O1 N1 C15 C14 -173.52(17) . . . . ?
O1 N1 C15 C16 -0.7(3) . . . . ?
C13 C14 C15 N1 55.6(3) . . . . ?
C9 C14 C15 N1 -129.7(2) . . . . ?
C13 C14 C15 C16 -117.6(2) . . . . ?
C9 C14 C15 C16 57.1(3) . . . . ?
