#------------------------------------------------------------------------------
#$Date: 2022-03-05 00:24:57 +0200 (Sat, 05 Mar 2022) $
#$Revision: 273429 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/85/7158504.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_7158504
loop_
_publ_author_name
'Ma, Wei-Wei'
'Yang, Chao'
'Xie, Qiang'
'Xu, Yun-He'
_publ_section_title
;
 Dienylation of N-benzoylhydrazones with CF₃-substituted
 homoallenylboronates in water.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1386
_journal_page_last               1390
_journal_paper_doi               10.1039/d1ob02335g
_journal_volume                  20
_journal_year                    2022
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H23 F3 N2 O'
_chemical_formula_sum            'C22 H23 F3 N2 O'
_chemical_formula_weight         388.42
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_Hall           'R 3 -2"c'
_space_group_name_H-M_alt        'R 3 c :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-11-08 deposited with the CCDC.	2022-01-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   32.7473(4)
_cell_length_b                   32.7473(4)
_cell_length_c                   9.72720(10)
_cell_measurement_reflns_used    9864
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      53.983
_cell_measurement_theta_min      4.700
_cell_volume                     9033.78(18)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      170.04
_diffrn_measured_fraction_theta_full 0.998
_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           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            32549
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.925
_diffrn_reflns_theta_min         4.699
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.529
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1273 before and 0.0610 after correction. The Ratio of minimum to maximum transmission is 0.8262. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             3672
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.108
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1287 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3536
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0336
_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)+(0.0378P)²+1.8553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0771
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_full    0.858
_reflns_Friedel_fraction_max     0.852
_reflns_number_gt                3163
_reflns_number_total             3536
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob02335g2.cif
_cod_data_source_block           190920mww_0m
_cod_depositor_comments          'Adding full bibliography for 7158504.cif.'
_cod_original_cell_volume        9033.8(2)
_cod_original_sg_symbol_H-M      'R 3 c'
_cod_database_code               7158504
_shelx_shelxl_version_number     2016/6
_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   0.969
_shelx_estimated_absorpt_t_min   0.939
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'
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 0.29340(6) 0.56488(6) 0.5977(2) 0.0570(5) Uani 1 1 d . . . . .
F2 F 0.31312(5) 0.55880(6) 0.80422(17) 0.0521(4) Uani 1 1 d . . . . .
F3 F 0.35088(6) 0.62475(6) 0.69660(19) 0.0571(5) Uani 1 1 d . . . . .
O1 O 0.43379(7) 0.53613(6) 0.19459(18) 0.0399(4) Uani 1 1 d . . . . .
N1 N 0.38880(7) 0.55280(7) 0.3999(2) 0.0339(5) Uani 1 1 d . . . . .
N2 N 0.43282(7) 0.55475(8) 0.4181(2) 0.0358(5) Uani 1 1 d . . . . .
H2 H 0.446262 0.560250 0.499563 0.043 Uiso 1 1 calc R . . . .
C1 C 0.34847(8) 0.50666(8) 0.4441(3) 0.0336(5) Uani 1 1 d . . . . .
H1 H 0.355856 0.480957 0.426497 0.040 Uiso 1 1 calc R . . . .
C2 C 0.34458(8) 0.51223(9) 0.5981(3) 0.0327(5) Uani 1 1 d . . . . .
C3 C 0.36527(8) 0.56456(8) 0.6270(3) 0.0333(6) Uani 1 1 d . . . . .
H3 H 0.391449 0.574665 0.695163 0.040 Uiso 1 1 calc R . . . .
C4 C 0.38635(10) 0.58851(9) 0.4881(3) 0.0381(6) Uani 1 1 d . . . . .
H4A H 0.366153 0.599431 0.444760 0.046 Uiso 1 1 calc R . . . .
H4B H 0.418247 0.616067 0.501682 0.046 Uiso 1 1 calc R . . . .
C5 C 0.33073(9) 0.57801(9) 0.6806(3) 0.0418(6) Uani 1 1 d . . . . .
C6 C 0.30498(10) 0.49779(10) 0.3596(3) 0.0453(7) Uani 1 1 d . . . . .
H6 H 0.301013 0.526010 0.369442 0.054 Uiso 1 1 calc R . . . .
C7 C 0.31321(12) 0.49251(11) 0.2080(3) 0.0571(9) Uani 1 1 d . . . . .
H7A H 0.342243 0.520447 0.177233 0.086 Uiso 1 1 calc GR . . . .
H7B H 0.286517 0.489288 0.153835 0.086 Uiso 1 1 calc GR . . . .
H7C H 0.316166 0.464408 0.195404 0.086 Uiso 1 1 calc GR . . . .
C8 C 0.26004(10) 0.45480(13) 0.4116(4) 0.0640(9) Uani 1 1 d . . . . .
H8A H 0.263340 0.426739 0.404328 0.096 Uiso 1 1 calc GR . . . .
H8B H 0.233180 0.450373 0.355871 0.096 Uiso 1 1 calc GR . . . .
H8C H 0.254742 0.459689 0.507829 0.096 Uiso 1 1 calc GR . . . .
C9 C 0.32922(9) 0.47935(9) 0.6953(3) 0.0381(6) Uani 1 1 d . . . . .
H9 H 0.330218 0.489746 0.787011 0.046 Uiso 1 1 calc R . . . .
C10 C 0.31068(9) 0.42811(9) 0.6757(3) 0.0371(6) Uani 1 1 d . . . . .
C11 C 0.33763(9) 0.41101(9) 0.6169(3) 0.0387(6) Uani 1 1 d . . . . .
H11 H 0.368825 0.432493 0.587339 0.046 Uiso 1 1 calc R . . . .
C12 C 0.31977(11) 0.36300(10) 0.6006(3) 0.0464(7) Uani 1 1 d . . . . .
H12 H 0.338653 0.351755 0.559897 0.056 Uiso 1 1 calc R . . . .
C13 C 0.27457(11) 0.33157(10) 0.6434(3) 0.0487(7) Uani 1 1 d . . . . .
H13 H 0.262103 0.298662 0.631084 0.058 Uiso 1 1 calc R . . . .
C14 C 0.24774(11) 0.34781(11) 0.7035(4) 0.0557(8) Uani 1 1 d . . . . .
H14 H 0.216700 0.326146 0.733906 0.067 Uiso 1 1 calc R . . . .
C15 C 0.26556(11) 0.39553(10) 0.7203(4) 0.0523(8) Uani 1 1 d . . . . .
H15 H 0.246664 0.406383 0.763035 0.063 Uiso 1 1 calc R . . . .
C16 C 0.45333(9) 0.54797(8) 0.3077(3) 0.0329(5) Uani 1 1 d . . . . .
C17 C 0.50187(9) 0.55577(9) 0.3287(3) 0.0348(6) Uani 1 1 d . . . . .
C18 C 0.53246(9) 0.58663(10) 0.4277(3) 0.0427(7) Uani 1 1 d . . . . .
H18 H 0.522004 0.602232 0.488439 0.051 Uiso 1 1 calc R . . . .
C19 C 0.57809(10) 0.59464(12) 0.4378(3) 0.0551(8) Uani 1 1 d . . . . .
H19 H 0.598939 0.615867 0.505039 0.066 Uiso 1 1 calc R . . . .
C20 C 0.59321(12) 0.57185(12) 0.3505(4) 0.0611(9) Uani 1 1 d . . . . .
H20 H 0.624624 0.577664 0.356789 0.073 Uiso 1 1 calc R . . . .
C21 C 0.56287(12) 0.54062(12) 0.2540(4) 0.0625(9) Uani 1 1 d . . . . .
H21 H 0.573235 0.524330 0.195695 0.075 Uiso 1 1 calc R . . . .
C22 C 0.51730(11) 0.53277(10) 0.2414(3) 0.0478(7) Uani 1 1 d . . . . .
H22 H 0.496763 0.511743 0.173268 0.057 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 0.0148 0.0070 '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 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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
N2 N1 C1 112.00(18) . . ?
N2 N1 C4 110.20(19) . . ?
C4 N1 C1 105.21(19) . . ?
N1 N2 H2 120.9 . . ?
C16 N2 N1 118.2(2) . . ?
C16 N2 H2 120.9 . . ?
N1 C1 H1 109.8 . . ?
N1 C1 C2 104.34(18) . . ?
N1 C1 C6 107.7(2) . . ?
C2 C1 H1 109.8 . . ?
C2 C1 C6 115.0(2) . . ?
C6 C1 H1 109.8 . . ?
C3 C2 C1 107.5(2) . . ?
C9 C2 C1 128.6(2) . . ?
C9 C2 C3 123.8(2) . . ?
C2 C3 H3 108.7 . . ?
C2 C3 C4 104.2(2) . . ?
C4 C3 H3 108.7 . . ?
C5 C3 C2 114.8(2) . . ?
C5 C3 H3 108.7 . . ?
C5 C3 C4 111.5(2) . . ?
N1 C4 C3 107.02(19) . . ?
N1 C4 H4A 110.3 . . ?
N1 C4 H4B 110.3 . . ?
C3 C4 H4A 110.3 . . ?
C3 C4 H4B 110.3 . . ?
H4A C4 H4B 108.6 . . ?
F1 C5 F2 106.2(2) . . ?
F1 C5 C3 113.4(2) . . ?
F2 C5 C3 112.5(2) . . ?
F3 C5 F1 106.6(2) . . ?
F3 C5 F2 106.4(2) . . ?
F3 C5 C3 111.3(2) . . ?
C1 C6 H6 108.0 . . ?
C7 C6 C1 109.8(2) . . ?
C7 C6 H6 108.0 . . ?
C7 C6 C8 111.1(3) . . ?
C8 C6 C1 111.8(2) . . ?
C8 C6 H6 108.0 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C9 H9 116.5 . . ?
C2 C9 C10 126.9(2) . . ?
C10 C9 H9 116.5 . . ?
C11 C10 C9 121.8(2) . . ?
C11 C10 C15 117.8(3) . . ?
C15 C10 C9 120.4(2) . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 120.9(3) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.3(3) . . ?
C14 C15 H15 119.4 . . ?
O1 C16 N2 122.8(2) . . ?
O1 C16 C17 121.1(2) . . ?
N2 C16 C17 116.1(2) . . ?
C18 C17 C16 122.5(2) . . ?
C22 C17 C16 118.0(2) . . ?
C22 C17 C18 119.5(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(3) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.1(3) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.5(3) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 H22 120.2 . . ?
C21 C22 C17 119.7(3) . . ?
C21 C22 H22 120.2 . . ?
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 C5 1.343(3) . ?
F2 C5 1.346(3) . ?
F3 C5 1.339(3) . ?
O1 C16 1.234(3) . ?
N1 N2 1.422(3) . ?
N1 C1 1.489(3) . ?
N1 C4 1.485(3) . ?
N2 H2 0.8800 . ?
N2 C16 1.343(3) . ?
C1 H1 1.0000 . ?
C1 C2 1.522(4) . ?
C1 C6 1.541(3) . ?
C2 C3 1.521(3) . ?
C2 C9 1.328(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.541(4) . ?
C3 C5 1.498(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 H6 1.0000 . ?
C6 C7 1.524(4) . ?
C6 C8 1.527(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9 0.9500 . ?
C9 C10 1.484(4) . ?
C10 C11 1.384(4) . ?
C10 C15 1.390(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.379(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.365(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.377(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.493(4) . ?
C17 C18 1.393(4) . ?
C17 C22 1.387(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.385(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.376(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.378(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(4) . ?
C22 H22 0.9500 . ?
