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#$Date: 2022-07-07 01:13:56 +0300 (Thu, 07 Jul 2022) $
#$Revision: 276704 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/72/1567247.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_1567247
loop_
_publ_author_name
'Li, Xinwei'
'Cheng, Zengrui'
'Liu, Jianzhong'
'Zhang, Ziyao'
'Song, Song'
'Jiao, Ning'
_publ_section_title
;
 Selective Desaturation of Amides: A Direct Approach to Enamides
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC02210A
_journal_year                    2022
_chemical_formula_sum            'C12 H11 Br I N O'
_chemical_formula_weight         392.03
_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_method           SHELXL-2018/3
_audit_update_record
;
2021-07-18 deposited with the CCDC.	2022-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.111(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.7902(14)
_cell_length_b                   6.2266(4)
_cell_length_c                   20.7782(14)
_cell_measurement_reflns_used    7085
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.51
_cell_volume                     2503.4(3)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0310
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8284
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.002
_diffrn_reflns_theta_max         25.002
_diffrn_reflns_theta_min         2.585
_exptl_absorpt_coefficient_mu    5.729
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.2580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    2.080
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.545
_refine_diff_density_min         -1.016
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0239
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0265P)²+5.5770P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0604
_refine_ls_wR_factor_ref         0.0612
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2084
_reflns_number_total             2194
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc02210a2.cif
_cod_data_source_block           20181124pku_0m_a
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1567247
_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_min   0.365
_shelx_estimated_absorpt_t_max   0.461
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 0.09058(2) 0.14739(5) 0.21342(2) 0.03405(11) Uani 1 1 d . . . . .
C1 C 0.26952(15) 0.3462(4) 0.34070(13) 0.0197(6) Uani 1 1 d . . . . .
H1 H 0.314394 0.289566 0.357117 0.024 Uiso 1 1 calc R U . . .
C2 C 0.22186(14) 0.2291(4) 0.29518(13) 0.0211(6) Uani 1 1 d . . . . .
H2 H 0.234002 0.093019 0.280302 0.025 Uiso 1 1 calc R U . . .
C3 C 0.15673(15) 0.3133(5) 0.27197(13) 0.0225(6) Uani 1 1 d . . . . .
C4 C 0.13840(15) 0.5151(5) 0.29106(14) 0.0263(6) Uani 1 1 d . . . . .
H4 H 0.093895 0.572948 0.273688 0.032 Uiso 1 1 calc R U . . .
C5 C 0.18654(17) 0.6301(4) 0.33604(14) 0.0256(6) Uani 1 1 d . . . . .
H5 H 0.174864 0.768988 0.349225 0.031 Uiso 1 1 calc R U . . .
C6 C 0.25160(14) 0.5462(4) 0.36223(13) 0.0198(5) Uani 1 1 d . . . . .
C7 C 0.30045(15) 0.6844(4) 0.40932(14) 0.0232(6) Uani 1 1 d . . . . .
C8 C 0.33998(17) 0.3650(4) 0.48398(15) 0.0260(6) Uani 1 1 d . . . . .
H8A H 0.375120 0.277760 0.468284 0.031 Uiso 1 1 calc R U . . .
H8B H 0.293856 0.304984 0.464648 0.031 Uiso 1 1 calc R U . . .
C9 C 0.35240(18) 0.3536(5) 0.55812(15) 0.0311(7) Uani 1 1 d . . . . .
H9A H 0.350128 0.202013 0.571836 0.037 Uiso 1 1 calc R U . . .
H9B H 0.315561 0.433992 0.573418 0.037 Uiso 1 1 calc R U . . .
C10 C 0.42259(16) 0.4473(5) 0.59022(15) 0.0294(6) Uani 1 1 d . . . . .
H10A H 0.425014 0.469524 0.637827 0.035 Uiso 1 1 calc R U . . .
H10B H 0.459745 0.346204 0.585175 0.035 Uiso 1 1 calc R U . . .
C11 C 0.43233(15) 0.6561(4) 0.55829(14) 0.0207(6) Uani 1 1 d . . . . .
C12 C 0.39489(14) 0.7206(4) 0.50096(13) 0.0219(6) Uani 1 1 d . . . . .
H12 H 0.402789 0.859826 0.485377 0.026 Uiso 1 1 calc R U . . .
I1 I 0.50961(2) 0.85965(3) 0.60888(2) 0.02954(10) Uani 1 1 d . . . . .
N1 N 0.34376(12) 0.5900(4) 0.46227(11) 0.0210(5) Uani 1 1 d . . . . .
O1 O 0.30186(14) 0.8787(3) 0.40029(12) 0.0398(6) Uani 1 1 d . . . . .
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'
I I -0.4742 1.8119 '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
C2 C1 C6 120.3(3) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 121.6(3) . . ?
C2 C3 Br1 119.0(2) . . ?
C4 C3 Br1 119.3(2) . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 C7 117.3(2) . . ?
C1 C6 C7 123.4(3) . . ?
O1 C7 N1 120.9(3) . . ?
O1 C7 C6 120.0(3) . . ?
N1 C7 C6 119.1(2) . . ?
N1 C8 C9 110.3(2) . . ?
N1 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 C10 111.5(3) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 109.3(2) . . ?
C11 C10 H10A 109.8 . . ?
C9 C10 H10A 109.8 . . ?
C11 C10 H10B 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
C12 C11 C10 124.3(3) . . ?
C12 C11 I1 118.7(2) . . ?
C10 C11 I1 117.0(2) . . ?
C11 C12 N1 122.4(2) . . ?
C11 C12 H12 118.8 . . ?
N1 C12 H12 118.8 . . ?
C7 N1 C12 117.5(2) . . ?
C7 N1 C8 125.8(2) . . ?
C12 N1 C8 116.7(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
Br1 C3 1.896(3) . ?
C1 C2 1.393(4) . ?
C1 C6 1.394(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.381(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(4) . ?
C4 C5 1.386(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.495(4) . ?
C7 O1 1.226(3) . ?
C7 N1 1.377(4) . ?
C8 N1 1.478(3) . ?
C8 C9 1.510(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.525(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.490(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.326(4) . ?
C11 I1 2.092(3) . ?
C12 N1 1.411(4) . ?
C12 H12 0.9500 . ?
