#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:59:32 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299079 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/03/7160305.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_7160305
loop_
_publ_author_name
'Liu, Qian'
'Yoshikawa, Isao'
'Okuyama, Kohsaku'
'Kudo, Kazuaki'
_publ_section_title
;
 Asymmetric synthesis of spiro[oxindole-3,2'-pyrrolidine]s through
 organocatalytic 1,3-dipolar cycloaddition via cycloreversion of
 precursor isatinimine homodimers.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1098
_journal_page_last               1103
_journal_paper_doi               10.1039/d4ob01727g
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H16 Br N3 O2'
_chemical_formula_sum            'C20 H16 Br N3 O2'
_chemical_formula_weight         410.27
_chemical_name_systematic        adduct_6i
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-10-23 deposited with the CCDC.	2024-12-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.89950(10)
_cell_length_b                   10.5371(2)
_cell_length_c                   21.3743(3)
_cell_measurement_reflns_used    6200
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      72.2410
_cell_measurement_theta_min      4.1580
_cell_volume                     1779.15(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.107a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10363
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.011
_diffrn_reflns_theta_min         4.137
_diffrn_source                   'rotating anode X-ray generator'
_exptl_absorpt_coefficient_mu    3.313
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79272
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform and hexane'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1362 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.029(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3451
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0248
_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)+(0.0337P)²+0.5855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0673
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                3322
_reflns_number_total             3451
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01727g2.cif
_cod_data_source_block           adduct_6i
_cod_depositor_comments          'Adding full bibliography for 7160305.cif.'
_cod_database_code               7160305
_shelx_shelxl_version_number     2019/3
_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   0.557
_shelx_estimated_absorpt_t_max   0.968
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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 0.72520(4) 0.80109(4) 0.19619(2) 0.02627(11) Uani 1 1 d . . . . .
C1 C 0.5233(4) 0.7234(3) 0.16545(15) 0.0206(7) Uani 1 1 d . . . . .
C2 C 0.5338(4) 0.6126(3) 0.13025(16) 0.0215(7) Uani 1 1 d . . . . .
H1 H 0.640252 0.573704 0.122408 0.026 Uiso 1 1 calc R U . . .
C3 C 0.3854(4) 0.5600(3) 0.10681(16) 0.0196(7) Uani 1 1 d . . . . .
H2 H 0.390855 0.484848 0.082299 0.024 Uiso 1 1 calc R U . . .
C4 C 0.2289(4) 0.6159(3) 0.11877(13) 0.0158(6) Uani 1 1 d . . . . .
C5 C 0.2231(4) 0.7259(3) 0.15551(14) 0.0191(6) Uani 1 1 d . . . . .
H3 H 0.116847 0.763994 0.164506 0.023 Uiso 1 1 calc R U . . .
C6 C 0.3695(4) 0.7800(3) 0.17890(14) 0.0213(7) Uani 1 1 d . . . . .
H4 H 0.364493 0.854592 0.203764 0.026 Uiso 1 1 calc R U . . .
C7 C 0.0654(4) 0.5626(3) 0.09305(15) 0.0154(6) Uani 1 1 d . . . . .
H5 H -0.030104 0.608443 0.113889 0.018 Uiso 1 1 calc R U . . .
C8 C 0.0399(4) 0.4194(3) 0.10447(15) 0.0168(6) Uani 1 1 d . . . . .
H6 H 0.145798 0.370965 0.095160 0.020 Uiso 1 1 calc R U . . .
N1 N -0.0938(3) 0.3886(3) 0.05930(12) 0.0173(6) Uani 1 1 d . . . . .
H7 H -0.119(5) 0.306(4) 0.0551(18) 0.026 Uiso 1 1 d . U . . .
C9 C -0.0442(4) 0.4470(3) 0.00002(14) 0.0175(6) Uani 1 1 d . . . . .
C10 C 0.0406(4) 0.5753(3) 0.02145(15) 0.0168(6) Uani 1 1 d . . . . .
H8 H 0.154020 0.583124 0.001046 0.020 Uiso 1 1 calc R U . . .
C11 C -0.0179(4) 0.3957(3) 0.16923(16) 0.0197(7) Uani 1 1 d . . . . .
N2 N -0.0607(4) 0.3801(3) 0.21967(14) 0.0274(7) Uani 1 1 d . . . . .
C12 C -0.0667(4) 0.6867(3) 0.00278(15) 0.0208(7) Uani 1 1 d . . . . .
H9 H -0.070419 0.708423 -0.040336 0.025 Uiso 1 1 calc R U . . .
O1 O -0.1485(4) 0.7506(3) 0.03862(12) 0.0319(6) Uani 1 1 d . . . . .
C13 C 0.0898(4) 0.3728(3) -0.03777(15) 0.0189(7) Uani 1 1 d . . . . .
N3 N 0.0282(4) 0.3531(3) -0.09661(13) 0.0237(6) Uani 1 1 d . . . . .
C14 C -0.1393(5) 0.3975(3) -0.10184(15) 0.0204(7) Uani 1 1 d . . . . .
C15 C -0.2470(5) 0.3875(3) -0.15255(15) 0.0257(8) Uani 1 1 d . . . . .
H10 H -0.210943 0.348998 -0.190468 0.031 Uiso 1 1 calc R U . . .
C16 C -0.4102(5) 0.4357(4) -0.14617(17) 0.0279(8) Uani 1 1 d . . . . .
H11 H -0.486395 0.431044 -0.180481 0.033 Uiso 1 1 calc R U . . .
C17 C -0.4633(5) 0.4905(4) -0.09056(18) 0.0255(8) Uani 1 1 d . . . . .
H12 H -0.575589 0.521875 -0.086966 0.031 Uiso 1 1 calc R U . . .
C18 C -0.3522(4) 0.4999(3) -0.03958(17) 0.0215(7) Uani 1 1 d . . . . .
H13 H -0.388318 0.537465 -0.001437 0.026 Uiso 1 1 calc R U . . .
C19 C -0.1893(4) 0.4536(3) -0.04578(14) 0.0169(6) Uani 1 1 d . . . . .
O2 O 0.2296(3) 0.3405(2) -0.01848(10) 0.0232(5) Uani 1 1 d . . . . .
C20 C 0.1211(5) 0.2934(4) -0.14759(17) 0.0365(9) Uani 1 1 d . . . . .
H14 H 0.242092 0.291663 -0.137425 0.055 Uiso 1 1 calc R U . . .
H15 H 0.103686 0.341853 -0.186180 0.055 Uiso 1 1 calc R U . . .
H16 H 0.080166 0.206388 -0.153462 0.055 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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 C1 C2 121.8(3) . . ?
C6 C1 Br1 118.5(2) . . ?
C2 C1 Br1 119.7(3) . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 H1 120.7 . . ?
C1 C2 H1 120.7 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H2 119.5 . . ?
C4 C3 H2 119.5 . . ?
C3 C4 C5 118.8(3) . . ?
C3 C4 C7 122.3(3) . . ?
C5 C4 C7 118.9(3) . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H3 119.5 . . ?
C4 C5 H3 119.5 . . ?
C5 C6 C1 118.8(3) . . ?
C5 C6 H4 120.6 . . ?
C1 C6 H4 120.6 . . ?
C4 C7 C8 114.6(3) . . ?
C4 C7 C10 115.8(3) . . ?
C8 C7 C10 102.9(3) . . ?
C4 C7 H5 107.7 . . ?
C8 C7 H5 107.7 . . ?
C10 C7 H5 107.7 . . ?
N1 C8 C11 110.9(3) . . ?
N1 C8 C7 101.9(2) . . ?
C11 C8 C7 110.7(3) . . ?
N1 C8 H6 111.0 . . ?
C11 C8 H6 111.0 . . ?
C7 C8 H6 111.0 . . ?
C9 N1 C8 106.5(2) . . ?
C9 N1 H7 112(3) . . ?
C8 N1 H7 116(3) . . ?
N1 C9 C19 112.2(3) . . ?
N1 C9 C13 115.1(3) . . ?
C19 C9 C13 101.8(2) . . ?
N1 C9 C10 102.9(2) . . ?
C19 C9 C10 118.2(3) . . ?
C13 C9 C10 107.2(3) . . ?
C12 C10 C7 113.6(3) . . ?
C12 C10 C9 110.7(3) . . ?
C7 C10 C9 105.5(3) . . ?
C12 C10 H8 109.0 . . ?
C7 C10 H8 109.0 . . ?
C9 C10 H8 109.0 . . ?
N2 C11 C8 178.4(4) . . ?
O1 C12 C10 124.7(3) . . ?
O1 C12 H9 117.6 . . ?
C10 C12 H9 117.6 . . ?
O2 C13 N3 126.1(3) . . ?
O2 C13 C9 125.6(3) . . ?
N3 C13 C9 108.4(3) . . ?
C13 N3 C14 111.0(3) . . ?
C13 N3 C20 125.1(3) . . ?
C14 N3 C20 123.9(3) . . ?
C15 C14 C19 122.2(3) . . ?
C15 C14 N3 128.0(3) . . ?
C19 C14 N3 109.8(3) . . ?
C14 C15 C16 117.7(3) . . ?
C14 C15 H10 121.1 . . ?
C16 C15 H10 121.1 . . ?
C17 C16 C15 121.1(3) . . ?
C17 C16 H11 119.5 . . ?
C15 C16 H11 119.5 . . ?
C16 C17 C18 120.4(3) . . ?
C16 C17 H12 119.8 . . ?
C18 C17 H12 119.8 . . ?
C19 C18 C17 118.9(3) . . ?
C19 C18 H13 120.6 . . ?
C17 C18 H13 120.6 . . ?
C18 C19 C14 119.7(3) . . ?
C18 C19 C9 131.4(3) . . ?
C14 C19 C9 108.8(3) . . ?
N3 C20 H14 109.5 . . ?
N3 C20 H15 109.5 . . ?
H14 C20 H15 109.5 . . ?
N3 C20 H16 109.5 . . ?
H14 C20 H16 109.5 . . ?
H15 C20 H16 109.5 . . ?
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 1.909(3) . ?
C1 C6 1.383(5) . ?
C1 C2 1.392(5) . ?
C2 C3 1.390(5) . ?
C2 H1 0.9500 . ?
C3 C4 1.394(5) . ?
C3 H2 0.9500 . ?
C4 C5 1.401(4) . ?
C4 C7 1.512(5) . ?
C5 C6 1.382(5) . ?
C5 H3 0.9500 . ?
C6 H4 0.9500 . ?
C7 C8 1.542(4) . ?
C7 C10 1.549(4) . ?
C7 H5 1.0000 . ?
C8 N1 1.467(4) . ?
C8 C11 1.479(4) . ?
C8 H6 1.0000 . ?
N1 C9 1.462(4) . ?
N1 H7 0.90(4) . ?
C9 C19 1.509(4) . ?
C9 C13 1.544(4) . ?
C9 C10 1.576(4) . ?
C10 C12 1.502(4) . ?
C10 H8 1.0000 . ?
C11 N2 1.142(4) . ?
C12 O1 1.208(4) . ?
C12 H9 0.9500 . ?
C13 O2 1.227(4) . ?
C13 N3 1.364(4) . ?
N3 C14 1.408(4) . ?
N3 C20 1.457(4) . ?
C14 C15 1.382(5) . ?
C14 C19 1.393(5) . ?
C15 C16 1.392(5) . ?
C15 H10 0.9500 . ?
C16 C17 1.386(6) . ?
C16 H11 0.9500 . ?
C17 C18 1.402(5) . ?
C17 H12 0.9500 . ?
C18 C19 1.383(5) . ?
C18 H13 0.9500 . ?
C20 H14 0.9800 . ?
C20 H15 0.9800 . ?
C20 H16 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C8 H6 O2 1.00 2.54 3.138(4) 118.3 . yes
N1 H7 O2 0.90(4) 2.10(4) 2.922(4) 151(3) 3_455 yes
C10 H8 O1 1.00 2.49 3.323(4) 140.1 3_565 yes
C15 H10 Br1 0.95 2.90 3.799(3) 159.3 2_564 yes
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
C6 C1 C2 C3 1.8(5) . . . . ?
Br1 C1 C2 C3 -178.1(2) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C2 C3 C4 C7 178.8(3) . . . . ?
C3 C4 C5 C6 1.0(5) . . . . ?
C7 C4 C5 C6 -178.5(3) . . . . ?
C4 C5 C6 C1 0.0(5) . . . . ?
C2 C1 C6 C5 -1.4(5) . . . . ?
Br1 C1 C6 C5 178.5(2) . . . . ?
C3 C4 C7 C8 50.2(4) . . . . ?
C5 C4 C7 C8 -130.4(3) . . . . ?
C3 C4 C7 C10 -69.5(4) . . . . ?
C5 C4 C7 C10 109.9(3) . . . . ?
C4 C7 C8 N1 -163.0(3) . . . . ?
C10 C7 C8 N1 -36.3(3) . . . . ?
C4 C7 C8 C11 79.0(3) . . . . ?
C10 C7 C8 C11 -154.3(3) . . . . ?
C11 C8 N1 C9 164.6(3) . . . . ?
C7 C8 N1 C9 46.8(3) . . . . ?
C8 N1 C9 C19 -164.7(3) . . . . ?
C8 N1 C9 C13 79.6(3) . . . . ?
C8 N1 C9 C10 -36.6(3) . . . . ?
C4 C7 C10 C12 -98.0(3) . . . . ?
C8 C7 C10 C12 136.1(3) . . . . ?
C4 C7 C10 C9 140.6(3) . . . . ?
C8 C7 C10 C9 14.7(3) . . . . ?
N1 C9 C10 C12 -111.2(3) . . . . ?
C19 C9 C10 C12 13.0(4) . . . . ?
C13 C9 C10 C12 127.1(3) . . . . ?
N1 C9 C10 C7 12.2(3) . . . . ?
C19 C9 C10 C7 136.4(3) . . . . ?
C13 C9 C10 C7 -109.5(3) . . . . ?
C7 C10 C12 O1 -10.8(5) . . . . ?
C9 C10 C12 O1 107.7(4) . . . . ?
N1 C9 C13 O2 -55.9(4) . . . . ?
C19 C9 C13 O2 -177.5(3) . . . . ?
C10 C9 C13 O2 57.8(4) . . . . ?
N1 C9 C13 N3 126.1(3) . . . . ?
C19 C9 C13 N3 4.5(3) . . . . ?
C10 C9 C13 N3 -120.2(3) . . . . ?
O2 C13 N3 C14 177.5(3) . . . . ?
C9 C13 N3 C14 -4.5(4) . . . . ?
O2 C13 N3 C20 -2.1(6) . . . . ?
C9 C13 N3 C20 175.9(3) . . . . ?
C13 N3 C14 C15 -175.7(3) . . . . ?
C20 N3 C14 C15 3.8(6) . . . . ?
C13 N3 C14 C19 2.7(4) . . . . ?
C20 N3 C14 C19 -177.8(3) . . . . ?
C19 C14 C15 C16 0.0(5) . . . . ?
N3 C14 C15 C16 178.1(3) . . . . ?
C14 C15 C16 C17 -0.8(5) . . . . ?
C15 C16 C17 C18 0.8(6) . . . . ?
C16 C17 C18 C19 0.0(5) . . . . ?
C17 C18 C19 C14 -0.8(5) . . . . ?
C17 C18 C19 C9 -178.4(3) . . . . ?
C15 C14 C19 C18 0.8(5) . . . . ?
N3 C14 C19 C18 -177.7(3) . . . . ?
C15 C14 C19 C9 178.9(3) . . . . ?
N3 C14 C19 C9 0.4(4) . . . . ?
N1 C9 C19 C18 51.4(5) . . . . ?
C13 C9 C19 C18 174.9(4) . . . . ?
C10 C9 C19 C18 -68.1(5) . . . . ?
N1 C9 C19 C14 -126.5(3) . . . . ?
C13 C9 C19 C14 -2.9(3) . . . . ?
C10 C9 C19 C14 114.1(3) . . . . ?
