#------------------------------------------------------------------------------
#$Date: 2021-01-07 06:53:32 +0200 (Thu, 07 Jan 2021) $
#$Revision: 260688 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/72/7127244.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_7127244
loop_
_publ_author_name
'Zhang, Dong'
'Dong, Shunxi'
'He, Qianwen'
'Luo, Yao'
'Liu, Yun'
'Liu, Xiaohua'
'Feng, Xiaoming'
_publ_section_title
;
 Enantioselective dicarbofunctionalization of (E)-alkenyloxindoles
 with pyridinium salts by chiral Lewis acid/photo relay catalysis.
;
_journal_issue                   84
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              12757
_journal_page_last               12760
_journal_paper_doi               10.1039/d0cc05621a
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C28 H27 Br N2 O4'
_chemical_formula_sum            'C28 H27 Br N2 O4'
_chemical_formula_weight         535.42
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2020-02-15 deposited with the CCDC.	2020-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.062(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9570(13)
_cell_length_b                   22.742(2)
_cell_length_c                   11.1670(11)
_cell_measurement_reflns_used    4019
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.92
_cell_measurement_theta_min      2.42
_cell_volume                     2613.8(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1800
_diffrn_reflns_av_unetI/netI     0.1143
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            48394
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.412
_diffrn_reflns_theta_min         2.642
_exptl_absorpt_coefficient_mu    1.608
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       stick
_exptl_crystal_F_000             1104
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, Hexane'
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         6514
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1485
_refine_ls_R_factor_gt           0.0585
_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)+(0.0445P)²+1.7411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1423
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3349
_reflns_number_total             6514
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc05621a2.cif
_cod_data_source_block           z
_cod_depositor_comments
'Adding full bibliography for 7127240--7127244.cif.'
_cod_original_cell_volume        2613.7(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7127244
_shelx_shelxl_version_number     2017/1
_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. 
;
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
Br Br 0.97908(5) 0.39264(2) 0.83535(4) 0.04444(16) Uani 1 1 d . . . . .
O1 O 1.0184(3) 0.41484(11) 0.4947(2) 0.0302(6) Uani 1 1 d . . . . .
O2 O 0.5961(3) 0.41470(13) 0.2668(3) 0.0466(8) Uani 1 1 d . . . . .
O3 O 0.7908(3) 0.40982(11) 0.2400(2) 0.0328(7) Uani 1 1 d . . . . .
O4 O 0.6249(3) 0.28148(13) 0.1691(3) 0.0440(8) Uani 1 1 d . . . . .
N1 N 0.8638(3) 0.47075(14) 0.5387(3) 0.0269(7) Uani 1 1 d D . . . .
H1N H 0.892(4) 0.5022(14) 0.532(4) 0.027(11) Uiso 1 1 d D . . . .
N2 N 0.9069(4) 0.26689(14) 0.5541(3) 0.0446(10) Uani 1 1 d . . . . .
C1 C 0.9182(4) 0.41977(16) 0.5188(3) 0.0265(8) Uani 1 1 d . . . . .
C2 C 0.8270(4) 0.36873(16) 0.5290(3) 0.0276(9) Uani 1 1 d . . . . .
C3 C 0.7562(4) 0.34502(16) 0.3892(4) 0.0305(9) Uani 1 1 d . . . . .
H3 H 0.820431 0.321857 0.362931 0.037 Uiso 1 1 calc R U . . .
C4 C 0.6427(4) 0.30426(17) 0.3840(4) 0.0369(10) Uani 1 1 d . . . . .
H4A H 0.673779 0.274375 0.452238 0.044 Uiso 1 1 calc R U . . .
H4B H 0.574196 0.327665 0.400882 0.044 Uiso 1 1 calc R U . . .
C5 C 0.5850(4) 0.27355(17) 0.2578(4) 0.0336(10) Uani 1 1 d . . . . .
C6 C 0.7036(4) 0.39366(18) 0.2931(4) 0.0332(9) Uani 1 1 d . . . . .
C7 C 0.7606(5) 0.45372(18) 0.1358(4) 0.0413(11) Uani 1 1 d . . . . .
C8 C 0.8867(6) 0.4576(2) 0.1104(5) 0.0591(15) Uani 1 1 d . . . . .
H8A H 0.910666 0.418453 0.088989 0.089 Uiso 1 1 calc R U . . .
H8B H 0.955055 0.472305 0.186613 0.089 Uiso 1 1 calc R U . . .
H8C H 0.876459 0.484449 0.039003 0.089 Uiso 1 1 calc R U . . .
C9 C 0.7293(5) 0.51248(19) 0.1839(5) 0.0543(13) Uani 1 1 d . . . . .
H9A H 0.798822 0.522927 0.263390 0.081 Uiso 1 1 calc R U . . .
H9B H 0.646839 0.509437 0.199530 0.081 Uiso 1 1 calc R U . . .
H9C H 0.722219 0.542919 0.119728 0.081 Uiso 1 1 calc R U . . .
C10 C 0.6517(7) 0.4304(2) 0.0220(5) 0.083(2) Uani 1 1 d . . . . .
H10A H 0.673803 0.390808 0.001279 0.125 Uiso 1 1 calc R U . . .
H10B H 0.639144 0.456420 -0.051168 0.125 Uiso 1 1 calc R U . . .
H10C H 0.571345 0.428730 0.041999 0.125 Uiso 1 1 calc R U . . .
C11 C 0.7569(4) 0.46088(16) 0.5794(3) 0.0263(8) Uani 1 1 d . . . . .
C12 C 0.7341(4) 0.40075(16) 0.5799(3) 0.0268(8) Uani 1 1 d . . . . .
C13 C 0.6404(4) 0.38026(18) 0.6266(4) 0.0319(9) Uani 1 1 d . . . . .
H13 H 0.625178 0.339284 0.630075 0.038 Uiso 1 1 calc R U . . .
C14 C 0.5691(4) 0.42080(19) 0.6683(4) 0.0378(10) Uani 1 1 d . . . . .
H14 H 0.503244 0.407399 0.699206 0.045 Uiso 1 1 calc R U . . .
C15 C 0.5926(4) 0.48048(19) 0.6655(4) 0.0384(10) Uani 1 1 d . . . . .
H15 H 0.542021 0.507234 0.694164 0.046 Uiso 1 1 calc R U . . .
C16 C 0.6888(4) 0.50261(17) 0.6215(4) 0.0318(9) Uani 1 1 d . . . . .
C17 C 0.7175(4) 0.56778(17) 0.6217(4) 0.0438(11) Uani 1 1 d . . . . .
H17A H 0.707247 0.580478 0.534947 0.066 Uiso 1 1 calc R U . . .
H17B H 0.806797 0.575336 0.678043 0.066 Uiso 1 1 calc R U . . .
H17C H 0.656957 0.589695 0.652321 0.066 Uiso 1 1 calc R U . . .
C21 C 0.9022(4) 0.31782(16) 0.6136(4) 0.0294(9) Uani 1 1 d . . . . .
C22 C 0.9621(4) 0.32099(17) 0.7444(4) 0.0343(10) Uani 1 1 d . . . . .
C23 C 1.0181(5) 0.27170(19) 0.8150(4) 0.0453(12) Uani 1 1 d . . . . .
H23 H 1.056875 0.274008 0.905110 0.054 Uiso 1 1 calc R U . . .
C24 C 1.0168(5) 0.2197(2) 0.7529(5) 0.0551(14) Uani 1 1 d . . . . .
H24 H 1.052054 0.184855 0.798669 0.066 Uiso 1 1 calc R U . . .
C25 C 0.9632(6) 0.2196(2) 0.6237(5) 0.0558(14) Uani 1 1 d . . . . .
H25 H 0.965627 0.184023 0.579842 0.067 Uiso 1 1 calc R U . . .
C31 C 0.4714(4) 0.23357(16) 0.2428(4) 0.0300(9) Uani 1 1 d . . . . .
C32 C 0.4552(4) 0.20598(17) 0.3460(4) 0.0354(10) Uani 1 1 d . . . . .
H32 H 0.515735 0.212796 0.429104 0.042 Uiso 1 1 calc R U . . .
C33 C 0.3517(4) 0.16851(18) 0.3300(4) 0.0417(11) Uani 1 1 d . . . . .
H33 H 0.342880 0.148680 0.401437 0.050 Uiso 1 1 calc R U . . .
C34 C 0.2612(4) 0.15985(17) 0.2106(4) 0.0395(11) Uani 1 1 d . . . . .
H34 H 0.189265 0.134548 0.200149 0.047 Uiso 1 1 calc R U . . .
C35 C 0.2743(4) 0.18763(18) 0.1063(4) 0.0427(11) Uani 1 1 d . . . . .
H35 H 0.211254 0.181985 0.024001 0.051 Uiso 1 1 calc R U . . .
C36 C 0.3800(4) 0.22382(18) 0.1223(4) 0.0390(11) Uani 1 1 d . . . . .
H36 H 0.390460 0.242295 0.050130 0.047 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'
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'
Br Br -0.2901 2.4595 '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
C6 O3 C7 122.1(3) . . ?
C1 N1 C11 112.1(3) . . ?
C21 N2 C25 119.4(4) . . ?
O1 C1 N1 126.4(3) . . ?
O1 C1 C2 126.4(3) . . ?
N1 C1 C2 107.2(3) . . ?
C12 C2 C21 114.7(3) . . ?
C12 C2 C1 101.5(3) . . ?
C21 C2 C1 112.5(3) . . ?
C12 C2 C3 111.7(3) . . ?
C21 C2 C3 109.1(3) . . ?
C1 C2 C3 106.9(3) . . ?
C6 C3 C4 108.0(3) . . ?
C6 C3 C2 113.0(3) . . ?
C4 C3 C2 111.1(3) . . ?
C5 C4 C3 112.9(3) . . ?
O4 C5 C31 120.7(4) . . ?
O4 C5 C4 122.5(4) . . ?
C31 C5 C4 116.8(3) . . ?
O2 C6 O3 124.6(4) . . ?
O2 C6 C3 124.3(4) . . ?
O3 C6 C3 111.1(4) . . ?
O3 C7 C8 102.4(4) . . ?
O3 C7 C10 108.9(3) . . ?
C8 C7 C10 111.9(4) . . ?
O3 C7 C9 109.4(3) . . ?
C8 C7 C9 110.3(4) . . ?
C10 C7 C9 113.4(4) . . ?
C16 C11 C12 123.6(4) . . ?
C16 C11 N1 127.1(3) . . ?
C12 C11 N1 109.1(3) . . ?
C13 C12 C11 119.4(4) . . ?
C13 C12 C2 131.5(3) . . ?
C11 C12 C2 109.1(3) . . ?
C12 C13 C14 118.6(4) . . ?
C15 C14 C13 120.8(4) . . ?
C14 C15 C16 122.0(4) . . ?
C11 C16 C15 115.5(4) . . ?
C11 C16 C17 122.4(4) . . ?
C15 C16 C17 122.1(4) . . ?
N2 C21 C22 118.8(4) . . ?
N2 C21 C2 116.5(3) . . ?
C22 C21 C2 124.7(3) . . ?
C21 C22 C23 121.0(4) . . ?
C21 C22 Br 122.3(3) . . ?
C23 C22 Br 116.6(3) . . ?
C24 C23 C22 119.0(4) . . ?
C25 C24 C23 117.7(4) . . ?
N2 C25 C24 123.8(4) . . ?
C32 C31 C36 118.7(4) . . ?
C32 C31 C5 121.5(3) . . ?
C36 C31 C5 119.8(4) . . ?
C31 C32 C33 120.6(4) . . ?
C34 C33 C32 120.1(4) . . ?
C35 C34 C33 120.3(4) . . ?
C34 C35 C36 119.4(4) . . ?
C35 C36 C31 120.9(4) . . ?
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
Br C22 1.895(4) . ?
O1 C1 1.221(5) . ?
O2 C6 1.210(5) . ?
O3 C6 1.337(5) . ?
O3 C7 1.482(5) . ?
O4 C5 1.225(5) . ?
N1 C1 1.357(5) . ?
N1 C11 1.412(5) . ?
N2 C21 1.345(5) . ?
N2 C25 1.347(6) . ?
C1 C2 1.561(5) . ?
C2 C12 1.513(5) . ?
C2 C21 1.542(5) . ?
C2 C3 1.580(5) . ?
C3 C6 1.511(5) . ?
C3 C4 1.536(5) . ?
C4 C5 1.504(5) . ?
C5 C31 1.504(6) . ?
C7 C8 1.506(7) . ?
C7 C10 1.510(6) . ?
C7 C9 1.522(6) . ?
C11 C16 1.385(5) . ?
C11 C12 1.390(5) . ?
C12 C13 1.382(5) . ?
C13 C14 1.389(6) . ?
C14 C15 1.384(6) . ?
C15 C16 1.400(6) . ?
C16 C17 1.515(5) . ?
C21 C22 1.382(5) . ?
C22 C23 1.387(6) . ?
C23 C24 1.368(6) . ?
C24 C25 1.359(7) . ?
C31 C32 1.377(5) . ?
C31 C36 1.392(5) . ?
C32 C33 1.380(6) . ?
C33 C34 1.375(6) . ?
C34 C35 1.375(6) . ?
C35 C36 1.382(6) . ?
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
C11 N1 C1 O1 -172.8(4) . . . . ?
C11 N1 C1 C2 8.6(4) . . . . ?
O1 C1 C2 C12 171.6(4) . . . . ?
N1 C1 C2 C12 -9.8(4) . . . . ?
O1 C1 C2 C21 48.5(5) . . . . ?
N1 C1 C2 C21 -132.9(3) . . . . ?
O1 C1 C2 C3 -71.2(5) . . . . ?
N1 C1 C2 C3 107.4(3) . . . . ?
C12 C2 C3 C6 64.2(4) . . . . ?
C21 C2 C3 C6 -167.9(3) . . . . ?
C1 C2 C3 C6 -46.0(4) . . . . ?
C12 C2 C3 C4 -57.2(4) . . . . ?
C21 C2 C3 C4 70.6(4) . . . . ?
C1 C2 C3 C4 -167.5(3) . . . . ?
C6 C3 C4 C5 64.2(4) . . . . ?
C2 C3 C4 C5 -171.4(3) . . . . ?
C3 C4 C5 O4 -0.9(6) . . . . ?
C3 C4 C5 C31 -178.8(3) . . . . ?
C7 O3 C6 O2 -3.8(6) . . . . ?
C7 O3 C6 C3 175.5(3) . . . . ?
C4 C3 C6 O2 33.9(5) . . . . ?
C2 C3 C6 O2 -89.4(5) . . . . ?
C4 C3 C6 O3 -145.4(3) . . . . ?
C2 C3 C6 O3 91.3(4) . . . . ?
C6 O3 C7 C8 179.2(3) . . . . ?
C6 O3 C7 C10 -62.2(5) . . . . ?
C6 O3 C7 C9 62.2(5) . . . . ?
C1 N1 C11 C16 172.2(4) . . . . ?
C1 N1 C11 C12 -3.5(4) . . . . ?
C16 C11 C12 C13 -1.2(6) . . . . ?
N1 C11 C12 C13 174.7(3) . . . . ?
C16 C11 C12 C2 -179.4(3) . . . . ?
N1 C11 C12 C2 -3.5(4) . . . . ?
C21 C2 C12 C13 -48.5(5) . . . . ?
C1 C2 C12 C13 -170.0(4) . . . . ?
C3 C2 C12 C13 76.3(5) . . . . ?
C21 C2 C12 C11 129.4(3) . . . . ?
C1 C2 C12 C11 7.9(4) . . . . ?
C3 C2 C12 C11 -105.7(3) . . . . ?
C11 C12 C13 C14 1.8(5) . . . . ?
C2 C12 C13 C14 179.6(4) . . . . ?
C12 C13 C14 C15 -1.1(6) . . . . ?
C13 C14 C15 C16 -0.3(6) . . . . ?
C12 C11 C16 C15 -0.3(6) . . . . ?
N1 C11 C16 C15 -175.4(4) . . . . ?
C12 C11 C16 C17 179.0(4) . . . . ?
N1 C11 C16 C17 3.8(6) . . . . ?
C14 C15 C16 C11 1.0(6) . . . . ?
C14 C15 C16 C17 -178.2(4) . . . . ?
C25 N2 C21 C22 3.6(6) . . . . ?
C25 N2 C21 C2 -175.4(4) . . . . ?
C12 C2 C21 N2 133.4(4) . . . . ?
C1 C2 C21 N2 -111.3(4) . . . . ?
C3 C2 C21 N2 7.2(5) . . . . ?
C12 C2 C21 C22 -45.6(5) . . . . ?
C1 C2 C21 C22 69.8(5) . . . . ?
C3 C2 C21 C22 -171.7(4) . . . . ?
N2 C21 C22 C23 -4.6(6) . . . . ?
C2 C21 C22 C23 174.3(4) . . . . ?
N2 C21 C22 Br 172.5(3) . . . . ?
C2 C21 C22 Br -8.6(6) . . . . ?
C21 C22 C23 C24 1.8(7) . . . . ?
Br C22 C23 C24 -175.5(4) . . . . ?
C22 C23 C24 C25 1.8(8) . . . . ?
C21 N2 C25 C24 0.1(8) . . . . ?
C23 C24 C25 N2 -2.9(9) . . . . ?
O4 C5 C31 C32 154.5(4) . . . . ?
C4 C5 C31 C32 -27.5(6) . . . . ?
O4 C5 C31 C36 -25.4(6) . . . . ?
C4 C5 C31 C36 152.5(4) . . . . ?
C36 C31 C32 C33 1.3(6) . . . . ?
C5 C31 C32 C33 -178.7(4) . . . . ?
C31 C32 C33 C34 -2.1(7) . . . . ?
C32 C33 C34 C35 1.1(7) . . . . ?
C33 C34 C35 C36 0.7(7) . . . . ?
C34 C35 C36 C31 -1.6(7) . . . . ?
C32 C31 C36 C35 0.6(6) . . . . ?
C5 C31 C36 C35 -179.5(4) . . . . ?
