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#$Date: 2022-08-23 03:31:13 +0300 (Tue, 23 Aug 2022) $
#$Revision: 277352 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/88/7158835.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_7158835
loop_
_publ_author_name
'Zhang, Jun-Hao'
'Jiang, Li-Lin'
'Hu, Sen-Jie'
'Li, Jiao-Zhe'
'Yu, Xuan-Chi'
'Liu, Fa-Liang'
'Guan, Yu-Tao'
'Lei, Ke-Wei'
'Wei, Wen-Ting'
_publ_section_title
;
 The polychloromethylation/acyloxylation of 1,6-enynes with chloroalkanes
 and diacyl peroxides through dual-role designs
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01330D
_journal_year                    2022
_chemical_formula_moiety         'C27 H22 Br Cl2 N O3'
_chemical_formula_sum            'C27 H22 Br Cl2 N O3'
_chemical_formula_weight         559.26
_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     dual
_audit_creation_date             2021-04-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-04-25 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.575(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3719(9)
_cell_length_b                   11.0520(9)
_cell_length_c                   18.6624(14)
_cell_measurement_reflns_used    4399
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.564
_cell_measurement_theta_min      2.503
_cell_volume                     2480.5(3)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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      170.0
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18682
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.420
_diffrn_reflns_theta_min         2.158
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.902
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0716 before and 0.0474 after correction. The Ratio of minimum to maximum transmission is 0.8133. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0425
_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)+(0.0333P)²+1.9670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0973
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3147
_reflns_number_total             5012
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01330d2.cif
_cod_data_source_block           0408zjh_0m
_cod_database_code               7158835
_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   0.928
_shelx_estimated_absorpt_t_min   0.763
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C20(H20), C6(H6), C16(H16), C19(H19), C2(H2), C23(H23),
 C18(H18), C17(H17), C27(H27), C26(H26), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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_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 0.95286(3) 0.77155(4) 0.80916(2) 0.05671(15) Uani 1 1 d . . . . .
Cl2 Cl 0.60242(8) 0.13641(8) 0.74924(5) 0.0506(3) Uani 1 1 d . . . . .
Cl1 Cl 0.48406(9) -0.07932(8) 0.68696(5) 0.0506(3) Uani 1 1 d . . . . .
O1 O 0.28251(16) 0.38419(17) 0.58263(11) 0.0294(5) Uani 1 1 d . . . . .
O2 O 0.74847(17) 0.23997(19) 0.63565(13) 0.0393(6) Uani 1 1 d . . . . .
N1 N 0.62812(19) 0.3954(2) 0.64713(14) 0.0263(6) Uani 1 1 d . . . . .
O3 O 0.2759(2) 0.4762(2) 0.47495(15) 0.0608(8) Uani 1 1 d . . . . .
C4 C 0.7029(2) 0.4808(3) 0.68728(17) 0.0266(7) Uani 1 1 d . . . . .
C8 C 0.6564(3) 0.2841(3) 0.62370(17) 0.0303(7) Uani 1 1 d . . . . .
C14 C 0.3514(2) 0.2930(3) 0.56327(16) 0.0270(7) Uani 1 1 d . . . . .
C15 C 0.2872(2) 0.1878(3) 0.52668(17) 0.0279(7) Uani 1 1 d . . . . .
C11 C 0.4601(2) 0.3109(3) 0.58221(16) 0.0262(7) Uani 1 1 d . . . . .
C12 C 0.5396(3) 0.0935(3) 0.60015(17) 0.0300(7) Uani 1 1 d . . . . .
H12A H 0.483649 0.052640 0.560977 0.036 Uiso 1 1 calc R . . . .
H12B H 0.611333 0.051395 0.603941 0.036 Uiso 1 1 calc R . . . .
C5 C 0.6701(3) 0.6006(3) 0.68966(17) 0.0318(7) Uani 1 1 d . . . . .
H5 H 0.596668 0.623572 0.665315 0.038 Uiso 1 1 calc R . . . .
C9 C 0.5523(2) 0.2251(3) 0.57540(17) 0.0275(7) Uani 1 1 d . . . . .
C7 C 0.5118(2) 0.4264(3) 0.61575(17) 0.0289(7) Uani 1 1 d . . . . .
H7A H 0.505759 0.490241 0.577813 0.035 Uiso 1 1 calc R . . . .
H7B H 0.475451 0.455065 0.654550 0.035 Uiso 1 1 calc R . . . .
C3 C 0.8093(3) 0.4477(3) 0.72601(19) 0.0379(8) Uani 1 1 d . . . . .
H3 H 0.831666 0.365315 0.727587 0.045 Uiso 1 1 calc R . . . .
C22 C 0.1663(2) 0.5547(3) 0.55431(19) 0.0328(8) Uani 1 1 d . . . . .
C20 C 0.2747(3) 0.1683(3) 0.45200(19) 0.0355(8) Uani 1 1 d . . . . .
H20 H 0.308842 0.221716 0.424062 0.043 Uiso 1 1 calc R . . . .
C13 C 0.5055(3) 0.0772(3) 0.67279(17) 0.0318(7) Uani 1 1 d . . . . .
H13 H 0.433200 0.120065 0.668930 0.038 Uiso 1 1 calc R . . . .
C1 C 0.8504(3) 0.6532(3) 0.76162(18) 0.0358(8) Uani 1 1 d . . . . .
C6 C 0.7431(3) 0.6868(3) 0.72711(18) 0.0350(8) Uani 1 1 d . . . . .
H6 H 0.719729 0.768393 0.729082 0.042 Uiso 1 1 calc R . . . .
C21 C 0.2450(3) 0.4709(3) 0.53079(19) 0.0334(8) Uani 1 1 d . . . . .
C10 C 0.5713(3) 0.2227(3) 0.49660(17) 0.0353(8) Uani 1 1 d . . . . .
H10A H 0.584576 0.305221 0.481418 0.053 Uiso 1 1 calc GR . . . .
H10B H 0.505389 0.189365 0.462616 0.053 Uiso 1 1 calc GR . . . .
H10C H 0.636015 0.172100 0.495714 0.053 Uiso 1 1 calc GR . . . .
C16 C 0.2347(3) 0.1093(3) 0.56592(19) 0.0366(8) Uani 1 1 d . . . . .
H16 H 0.240488 0.123184 0.616927 0.044 Uiso 1 1 calc R . . . .
C19 C 0.2122(3) 0.0704(3) 0.4174(2) 0.0419(9) Uani 1 1 d . . . . .
H19 H 0.203172 0.057938 0.365948 0.050 Uiso 1 1 calc R . . . .
C2 C 0.8820(3) 0.5346(3) 0.7620(2) 0.0425(9) Uani 1 1 d . . . . .
H2 H 0.954962 0.511804 0.787441 0.051 Uiso 1 1 calc R . . . .
C23 C 0.1525(3) 0.5544(3) 0.6256(2) 0.0411(9) Uani 1 1 d . . . . .
H23 H 0.193454 0.499158 0.660656 0.049 Uiso 1 1 calc R . . . .
C18 C 0.1636(3) -0.0080(3) 0.4577(2) 0.0460(10) Uani 1 1 d . . . . .
H18 H 0.122704 -0.075759 0.434438 0.055 Uiso 1 1 calc R . . . .
C17 C 0.1744(3) 0.0119(3) 0.5320(2) 0.0448(9) Uani 1 1 d . . . . .
H17 H 0.140174 -0.041696 0.559785 0.054 Uiso 1 1 calc R . . . .
C27 C 0.1059(3) 0.6338(3) 0.5028(2) 0.0492(10) Uani 1 1 d . . . . .
H27 H 0.115889 0.634951 0.453831 0.059 Uiso 1 1 calc R . . . .
C26 C 0.0309(3) 0.7111(3) 0.5234(3) 0.0625(12) Uani 1 1 d . . . . .
H26 H -0.011800 0.764898 0.488086 0.075 Uiso 1 1 calc R . . . .
C24 C 0.0795(4) 0.6343(4) 0.6459(3) 0.0648(13) Uani 1 1 d . . . . .
H24 H 0.071759 0.636386 0.695329 0.078 Uiso 1 1 calc R . . . .
C25 C 0.0177(4) 0.7110(4) 0.5938(3) 0.0667(13) Uani 1 1 d . . . . .
H25 H -0.034597 0.764334 0.607167 0.080 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'
Cl Cl 0.1484 0.1585 '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
C21 O1 C14 116.3(2) . . ?
C4 N1 C7 121.3(2) . . ?
C8 N1 C4 125.7(2) . . ?
C8 N1 C7 112.4(2) . . ?
C5 C4 N1 119.7(3) . . ?
C5 C4 C3 118.8(3) . . ?
C3 C4 N1 121.5(3) . . ?
O2 C8 N1 126.8(3) . . ?
O2 C8 C9 124.1(3) . . ?
N1 C8 C9 109.0(2) . . ?
O1 C14 C15 112.7(2) . . ?
C11 C14 O1 117.3(3) . . ?
C11 C14 C15 129.9(3) . . ?
C20 C15 C14 120.6(3) . . ?
C20 C15 C16 118.5(3) . . ?
C16 C15 C14 120.8(3) . . ?
C14 C11 C9 128.6(3) . . ?
C14 C11 C7 123.1(3) . . ?
C7 C11 C9 108.2(2) . . ?
H12A C12 H12B 107.3 . . ?
C9 C12 H12A 108.2 . . ?
C9 C12 H12B 108.2 . . ?
C13 C12 H12A 108.2 . . ?
C13 C12 H12B 108.2 . . ?
C13 C12 C9 116.6(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C8 C9 C12 110.8(3) . . ?
C8 C9 C10 105.8(2) . . ?
C11 C9 C8 103.3(2) . . ?
C11 C9 C12 115.7(2) . . ?
C11 C9 C10 112.2(2) . . ?
C10 C9 C12 108.6(2) . . ?
N1 C7 C11 104.6(2) . . ?
N1 C7 H7A 110.8 . . ?
N1 C7 H7B 110.8 . . ?
C11 C7 H7A 110.8 . . ?
C11 C7 H7B 110.8 . . ?
H7A C7 H7B 108.9 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.0 . . ?
C23 C22 C21 121.5(3) . . ?
C23 C22 C27 120.2(3) . . ?
C27 C22 C21 118.3(3) . . ?
C15 C20 H20 119.8 . . ?
C15 C20 C19 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
Cl2 C13 Cl1 109.77(18) . . ?
Cl2 C13 H13 108.0 . . ?
Cl1 C13 H13 108.0 . . ?
C12 C13 Cl2 113.5(2) . . ?
C12 C13 Cl1 109.3(2) . . ?
C12 C13 H13 108.0 . . ?
C6 C1 Br1 119.8(2) . . ?
C2 C1 Br1 120.1(3) . . ?
C2 C1 C6 120.1(3) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 C5 119.4(3) . . ?
C1 C6 H6 120.3 . . ?
O1 C21 C22 111.5(3) . . ?
O3 C21 O1 122.0(3) . . ?
O3 C21 C22 126.5(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 C20 120.0(3) . . ?
C18 C19 H19 120.0 . . ?
C3 C2 H2 119.6 . . ?
C1 C2 C3 120.8(3) . . ?
C1 C2 H2 119.6 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.1(3) . . ?
C24 C23 H23 120.0 . . ?
C19 C18 H18 120.1 . . ?
C19 C18 C17 119.9(3) . . ?
C17 C18 H18 120.1 . . ?
C16 C17 C18 120.1(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C22 C27 H27 120.4 . . ?
C26 C27 C22 119.1(4) . . ?
C26 C27 H27 120.4 . . ?
C27 C26 H26 119.7 . . ?
C25 C26 C27 120.6(4) . . ?
C25 C26 H26 119.7 . . ?
C23 C24 H24 120.3 . . ?
C25 C24 C23 119.4(4) . . ?
C25 C24 H24 120.3 . . ?
C26 C25 C24 120.5(4) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
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(3) . ?
Cl2 C13 1.760(3) . ?
Cl1 C13 1.779(3) . ?
O1 C14 1.420(3) . ?
O1 C21 1.363(4) . ?
O2 C8 1.211(3) . ?
N1 C4 1.408(4) . ?
N1 C8 1.378(4) . ?
N1 C7 1.461(4) . ?
O3 C21 1.193(4) . ?
C4 C5 1.388(4) . ?
C4 C3 1.393(4) . ?
C8 C9 1.533(4) . ?
C14 C15 1.481(4) . ?
C14 C11 1.323(4) . ?
C15 C20 1.383(4) . ?
C15 C16 1.391(4) . ?
C11 C9 1.512(4) . ?
C11 C7 1.498(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C9 1.544(4) . ?
C12 C13 1.522(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(4) . ?
C9 C10 1.543(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C3 H3 0.9500 . ?
C3 C2 1.378(4) . ?
C22 C21 1.483(4) . ?
C22 C23 1.380(5) . ?
C22 C27 1.382(5) . ?
C20 H20 0.9500 . ?
C20 C19 1.397(5) . ?
C13 H13 1.0000 . ?
C1 C6 1.383(5) . ?
C1 C2 1.368(5) . ?
C6 H6 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C16 H16 0.9500 . ?
C16 C17 1.377(5) . ?
C19 H19 0.9500 . ?
C19 C18 1.374(5) . ?
C2 H2 0.9500 . ?
C23 H23 0.9500 . ?
C23 C24 1.379(5) . ?
C18 H18 0.9500 . ?
C18 C17 1.379(5) . ?
C17 H17 0.9500 . ?
C27 H27 0.9500 . ?
C27 C26 1.381(5) . ?
C26 H26 0.9500 . ?
C26 C25 1.363(6) . ?
C24 H24 0.9500 . ?
C24 C25 1.378(6) . ?
C25 H25 0.9500 . ?
