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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/59/7105901.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_7105901
loop_
_publ_author_name
'Xiu-Chun Zhang'
'Shu-Hua Cao'
'Yin Wei'
'Min Shi'
_publ_section_title
;
 Phosphine-catalyzed Highly Diastereoselective [3+2] Cyclization of Isatin
 Derived Electron-deficient Alkenes with -Allenic Esters
;
_journal_name_full               Chem.Commun.
_journal_page_first              1548
_journal_paper_doi               10.1039/c0cc04289g
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C23 H16 Br N O2'
_chemical_formula_weight         418.28
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.032(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2650(17)
_cell_length_b                   13.415(3)
_cell_length_c                   16.413(3)
_cell_measurement_reflns_used    3397
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      53.953
_cell_measurement_theta_min      4.967
_cell_volume                     1818.6(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9725
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    2.278
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48225
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.401
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.147
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3572
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0585P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.0994
_reflns_number_gt                2619
_reflns_number_total             3572
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC04289G.TXT
_cod_data_source_block           cd201470
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7105901
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.91041(4) 0.23605(2) 0.239103(16) 0.06374(15) Uani 1 1 d . . .
N1 N 0.9175(2) 0.36429(15) 0.54645(11) 0.0408(5) Uani 1 1 d . . .
O1 O 0.8706(2) 0.45942(15) 0.65938(9) 0.0578(5) Uani 1 1 d . . .
O2 O 0.5371(2) 0.64022(13) 0.43329(9) 0.0505(5) Uani 1 1 d . . .
C1 C 0.8502(3) 0.44198(19) 0.58709(14) 0.0424(6) Uani 1 1 d . . .
C2 C 0.8706(3) 0.36783(18) 0.46364(13) 0.0379(6) Uani 1 1 d . . .
C3 C 0.9145(3) 0.3027(2) 0.40324(14) 0.0428(6) Uani 1 1 d . . .
H3 H 0.9825 0.2487 0.4143 0.051 Uiso 1 1 calc R . .
C4 C 0.8524(3) 0.3216(2) 0.32542(14) 0.0455(6) Uani 1 1 d . . .
C5 C 0.7508(3) 0.4006(2) 0.30741(14) 0.0475(6) Uani 1 1 d . . .
H5 H 0.7116 0.4106 0.2542 0.057 Uiso 1 1 calc R . .
C6 C 0.7075(3) 0.46483(19) 0.36867(13) 0.0435(6) Uani 1 1 d . . .
H6 H 0.6382 0.5179 0.3570 0.052 Uiso 1 1 calc R . .
C7 C 0.7682(3) 0.44973(17) 0.44790(12) 0.0356(5) Uani 1 1 d . . .
C8 C 0.7503(3) 0.50148(18) 0.52517(13) 0.0364(5) Uani 1 1 d . . .
C9 C 0.6758(3) 0.58325(18) 0.55194(13) 0.0411(6) Uani 1 1 d . . .
H9 H 0.6883 0.5958 0.6075 0.049 Uiso 1 1 calc R . .
C10 C 0.5769(3) 0.65561(18) 0.50516(13) 0.0392(6) Uani 1 1 d . . .
C11 C 0.5253(3) 0.74893(18) 0.54553(14) 0.0388(6) Uani 1 1 d . . .
C12 C 0.5561(4) 0.7705(2) 0.62760(16) 0.0541(7) Uani 1 1 d . . .
H12 H 0.6134 0.7253 0.6605 0.065 Uiso 1 1 calc R . .
C13 C 0.5023(4) 0.8584(2) 0.66037(16) 0.0632(8) Uani 1 1 d . . .
H13 H 0.5234 0.8719 0.7153 0.076 Uiso 1 1 calc R . .
C14 C 0.4188(4) 0.9255(2) 0.61339(19) 0.0634(8) Uani 1 1 d . . .
H14 H 0.3835 0.9848 0.6361 0.076 Uiso 1 1 calc R . .
C15 C 0.3867(4) 0.9058(2) 0.53269(18) 0.0643(8) Uani 1 1 d . . .
H15 H 0.3288 0.9516 0.5007 0.077 Uiso 1 1 calc R . .
C16 C 0.4397(3) 0.8187(2) 0.49878(16) 0.0524(7) Uani 1 1 d . . .
H16 H 0.4179 0.8063 0.4437 0.063 Uiso 1 1 calc R . .
C17 C 1.0391(3) 0.2975(2) 0.58318(15) 0.0455(6) Uani 1 1 d . . .
H17A H 1.0901 0.3308 0.6298 0.055 Uiso 1 1 calc R . .
H17B H 1.1220 0.2858 0.5439 0.055 Uiso 1 1 calc R . .
C18 C 0.9758(3) 0.19817(19) 0.61063(13) 0.0396(6) Uani 1 1 d . . .
C19 C 1.0509(3) 0.1111(2) 0.58779(15) 0.0531(7) Uani 1 1 d . . .
H19 H 1.1365 0.1137 0.5526 0.064 Uiso 1 1 calc R . .
C20 C 0.9997(4) 0.0204(2) 0.6168(2) 0.0647(8) Uani 1 1 d . . .
H20 H 1.0516 -0.0377 0.6013 0.078 Uiso 1 1 calc R . .
C21 C 0.8729(4) 0.0152(2) 0.66838(18) 0.0644(8) Uani 1 1 d . . .
H21 H 0.8388 -0.0461 0.6880 0.077 Uiso 1 1 calc R . .
C22 C 0.7969(3) 0.1015(2) 0.69070(16) 0.0562(7) Uani 1 1 d . . .
H22 H 0.7103 0.0986 0.7253 0.067 Uiso 1 1 calc R . .
C23 C 0.8482(3) 0.1920(2) 0.66227(14) 0.0470(6) Uani 1 1 d . . .
H23 H 0.7961 0.2500 0.6781 0.056 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'
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
C1 N1 C2 110.16(19) . . ?
C1 N1 C17 123.5(2) . . ?
C2 N1 C17 125.7(2) . . ?
O1 C1 N1 125.4(2) . . ?
O1 C1 C8 127.4(2) . . ?
N1 C1 C8 107.22(19) . . ?
C3 C2 N1 127.2(2) . . ?
C3 C2 C7 122.4(2) . . ?
N1 C2 C7 110.4(2) . . ?
C2 C3 C4 116.6(2) . . ?
C2 C3 H3 121.7 . . ?
C4 C3 H3 121.7 . . ?
C5 C4 C3 122.9(2) . . ?
C5 C4 Br1 118.24(18) . . ?
C3 C4 Br1 118.9(2) . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 119.7(2) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C2 118.7(2) . . ?
C6 C7 C8 134.3(2) . . ?
C2 C7 C8 106.96(19) . . ?
C9 C8 C7 137.5(2) . . ?
C9 C8 C1 117.2(2) . . ?
C7 C8 C1 105.2(2) . . ?
C8 C9 C10 128.6(2) . . ?
C8 C9 H9 115.7 . . ?
C10 C9 H9 115.7 . . ?
O2 C10 C9 121.0(2) . . ?
O2 C10 C11 119.8(2) . . ?
C9 C10 C11 119.1(2) . . ?
C16 C11 C12 117.8(2) . . ?
C16 C11 C10 118.1(2) . . ?
C12 C11 C10 124.1(2) . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.2(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.9(2) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
N1 C17 C18 115.2(2) . . ?
N1 C17 H17A 108.5 . . ?
C18 C17 H17A 108.5 . . ?
N1 C17 H17B 108.5 . . ?
C18 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C23 C18 C19 118.5(3) . . ?
C23 C18 C17 121.2(3) . . ?
C19 C18 C17 120.2(2) . . ?
C20 C19 C18 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 120.6(3) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 119.2(3) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C21 C22 C23 120.4(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 120.9(3) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?
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 C4 1.898(2) . ?
N1 C1 1.366(3) . ?
N1 C2 1.401(3) . ?
N1 C17 1.461(3) . ?
O1 C1 1.215(3) . ?
O2 C10 1.231(3) . ?
C1 C8 1.514(3) . ?
C2 C3 1.380(3) . ?
C2 C7 1.405(3) . ?
C3 C4 1.383(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.392(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.458(3) . ?
C8 C9 1.340(3) . ?
C9 C10 1.468(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.486(3) . ?
C11 C16 1.388(4) . ?
C11 C12 1.393(3) . ?
C12 C13 1.376(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.358(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.506(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C23 1.379(3) . ?
C18 C19 1.380(4) . ?
C19 C20 1.379(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.372(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.373(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.373(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
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
C2 N1 C1 O1 -178.9(2) . . . . ?
C17 N1 C1 O1 -7.3(4) . . . . ?
C2 N1 C1 C8 0.1(3) . . . . ?
C17 N1 C1 C8 171.7(2) . . . . ?
C1 N1 C2 C3 179.6(2) . . . . ?
C17 N1 C2 C3 8.2(4) . . . . ?
C1 N1 C2 C7 -0.3(3) . . . . ?
C17 N1 C2 C7 -171.7(2) . . . . ?
N1 C2 C3 C4 180.0(2) . . . . ?
C7 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C2 C3 C4 Br1 179.10(18) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
Br1 C4 C5 C6 -179.35(19) . . . . ?
C4 C5 C6 C7 0.6(4) . . . . ?
C5 C6 C7 C2 -1.1(4) . . . . ?
C5 C6 C7 C8 179.3(2) . . . . ?
C3 C2 C7 C6 0.8(3) . . . . ?
N1 C2 C7 C6 -179.3(2) . . . . ?
C3 C2 C7 C8 -179.5(2) . . . . ?
N1 C2 C7 C8 0.4(3) . . . . ?
C6 C7 C8 C9 -2.4(5) . . . . ?
C2 C7 C8 C9 177.9(3) . . . . ?
C6 C7 C8 C1 179.3(3) . . . . ?
C2 C7 C8 C1 -0.4(2) . . . . ?
O1 C1 C8 C9 0.5(4) . . . . ?
N1 C1 C8 C9 -178.5(2) . . . . ?
O1 C1 C8 C7 179.2(2) . . . . ?
N1 C1 C8 C7 0.2(3) . . . . ?
C7 C8 C9 C10 -0.4(5) . . . . ?
C1 C8 C9 C10 177.8(2) . . . . ?
C8 C9 C10 O2 8.4(4) . . . . ?
C8 C9 C10 C11 -171.3(2) . . . . ?
O2 C10 C11 C16 -3.3(4) . . . . ?
C9 C10 C11 C16 176.4(2) . . . . ?
O2 C10 C11 C12 176.1(2) . . . . ?
C9 C10 C11 C12 -4.1(4) . . . . ?
C16 C11 C12 C13 0.2(4) . . . . ?
C10 C11 C12 C13 -179.3(3) . . . . ?
C11 C12 C13 C14 -0.2(5) . . . . ?
C12 C13 C14 C15 0.3(5) . . . . ?
C13 C14 C15 C16 -0.5(5) . . . . ?
C14 C15 C16 C11 0.5(5) . . . . ?
C12 C11 C16 C15 -0.3(4) . . . . ?
C10 C11 C16 C15 179.1(3) . . . . ?
C1 N1 C17 C18 100.9(3) . . . . ?
C2 N1 C17 C18 -88.8(3) . . . . ?
N1 C17 C18 C23 -53.5(3) . . . . ?
N1 C17 C18 C19 129.9(2) . . . . ?
C23 C18 C19 C20 -0.6(4) . . . . ?
C17 C18 C19 C20 176.0(2) . . . . ?
C18 C19 C20 C21 0.4(4) . . . . ?
C19 C20 C21 C22 0.2(4) . . . . ?
C20 C21 C22 C23 -0.5(4) . . . . ?
C21 C22 C23 C18 0.3(4) . . . . ?
C19 C18 C23 C22 0.2(4) . . . . ?
C17 C18 C23 C22 -176.3(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653243
2 PubChem 53253844
