#------------------------------------------------------------------------------
#$Date: 2021-06-30 04:18:32 +0300 (Wed, 30 Jun 2021) $
#$Revision: 266795 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/37/1563783.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_1563783
loop_
_publ_author_name
'Zhong, Xia'
'Tan, Jiuqi'
'Qiao, Jianglin'
'Zhou, Yuqiao'
'Lv, Cidan'
'Su, Zhishan'
'Dong, Shunxi'
'Feng, Xiaoming'
_publ_section_title
;
 Asymmetric catalytic synthesis of spirocyclobutyl oxindoles and beyond
 via [2+2] cycloaddition and sequential transformations
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02681J
_journal_year                    2021
_chemical_formula_moiety         'C26 H22 N2 O5 S'
_chemical_formula_sum            'C26 H22 N2 O5 S'
_chemical_formula_weight         474.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-04-22 deposited with the CCDC.	2021-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                96.2200(10)
_cell_angle_beta                 95.7380(10)
_cell_angle_gamma                105.7620(10)
_cell_formula_units_Z            2
_cell_length_a                   8.3490(2)
_cell_length_b                   11.8120(3)
_cell_length_c                   14.8662(4)
_cell_measurement_reflns_used    9782
_cell_measurement_temperature    172(2)
_cell_measurement_theta_max      68.33
_cell_measurement_theta_min      3.02
_cell_volume                     1389.76(6)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      172(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            36253
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.323
_diffrn_reflns_theta_min         3.018
_exptl_absorpt_coefficient_mu    1.322
_exptl_absorpt_correction_T_max  0.9509
_exptl_absorpt_correction_T_min  0.7174
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_description       flake
_exptl_crystal_F_000             496
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: THF, hexane'
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4998
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0485P)²+0.8579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1110
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4334
_reflns_number_total             4998
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc02681j2.cif
_cod_data_source_block           zhx029
_cod_database_code               1563783
_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   0.657
_shelx_estimated_absorpt_t_max   0.899
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
S S 0.25472(5) 0.11315(4) 0.39850(3) 0.02786(12) Uani 1 1 d . . . . .
O1 O 0.10326(17) 0.02637(11) 0.40924(9) 0.0375(3) Uani 1 1 d . . . . .
O2 O 0.37829(18) 0.07946(12) 0.35057(9) 0.0373(3) Uani 1 1 d . . . . .
O3 O 0.23525(15) 0.29814(11) 0.59518(8) 0.0283(3) Uani 1 1 d . . . . .
O4 O 0.3091(2) 0.45052(12) 0.70847(11) 0.0466(4) Uani 1 1 d . . . . .
O5 O 0.57599(17) 0.41987(15) 0.90723(10) 0.0459(4) Uani 1 1 d . . . . .
N1 N 0.34938(17) 0.16913(12) 0.50325(10) 0.0251(3) Uani 1 1 d . . . . .
N2 N 0.3076(2) 0.39461(16) 0.94439(11) 0.0382(4) Uani 1 1 d D . . . .
H2N H 0.336(3) 0.455(2) 0.9914(16) 0.067(8) Uiso 1 1 d D . . . .
C1 C 0.1976(2) 0.22584(16) 0.34633(12) 0.0301(4) Uani 1 1 d . . . . .
C2 C 0.0459(3) 0.24722(19) 0.35813(14) 0.0409(5) Uani 1 1 d . . . . .
H2 H -0.026701 0.202529 0.395022 0.049 Uiso 1 1 calc R U . . .
C3 C 0.0012(3) 0.3350(2) 0.31526(16) 0.0524(6) Uani 1 1 d . . . . .
H3 H -0.103097 0.350041 0.322840 0.063 Uiso 1 1 calc R U . . .
C4 C 0.1068(3) 0.4012(2) 0.26141(16) 0.0493(6) Uani 1 1 d . . . . .
C5 C 0.2584(3) 0.3792(2) 0.25161(15) 0.0463(5) Uani 1 1 d . . . . .
H5 H 0.331737 0.424473 0.215318 0.056 Uiso 1 1 calc R U . . .
C6 C 0.3057(3) 0.29187(19) 0.29394(14) 0.0407(5) Uani 1 1 d . . . . .
H6 H 0.410755 0.277598 0.287062 0.049 Uiso 1 1 calc R U . . .
C7 C 0.0572(4) 0.4955(3) 0.2137(2) 0.0721(8) Uani 1 1 d . . . . .
H7A H 0.124921 0.513454 0.164112 0.108 Uiso 1 1 calc R U . . .
H7B H 0.076647 0.567690 0.257533 0.108 Uiso 1 1 calc R U . . .
H7C H -0.061973 0.466689 0.188584 0.108 Uiso 1 1 calc R U . . .
C11 C 0.5236(2) 0.23858(15) 0.51621(12) 0.0247(3) Uani 1 1 d . . . . .
C12 C 0.5681(2) 0.35709(16) 0.50368(14) 0.0326(4) Uani 1 1 d . . . . .
H12 H 0.484313 0.393024 0.484073 0.039 Uiso 1 1 calc R U . . .
C13 C 0.7351(2) 0.42267(17) 0.51985(16) 0.0399(5) Uani 1 1 d . . . . .
H13 H 0.766459 0.503763 0.510842 0.048 Uiso 1 1 calc R U . . .
C14 C 0.8570(2) 0.37030(19) 0.54921(15) 0.0406(5) Uani 1 1 d . . . . .
H14 H 0.971668 0.415696 0.560893 0.049 Uiso 1 1 calc R U . . .
C15 C 0.8117(2) 0.25207(18) 0.56150(15) 0.0373(4) Uani 1 1 d . . . . .
H15 H 0.895527 0.216402 0.581629 0.045 Uiso 1 1 calc R U . . .
C16 C 0.6444(2) 0.18516(16) 0.54458(13) 0.0308(4) Uani 1 1 d . . . . .
H16 H 0.613293 0.103645 0.552402 0.037 Uiso 1 1 calc R U . . .
C21 C 0.2506(2) 0.17821(14) 0.57658(11) 0.0248(3) Uani 1 1 d . . . . .
H21 H 0.136314 0.120559 0.559653 0.030 Uiso 1 1 calc R U . . .
C22 C 0.3316(2) 0.15496(16) 0.66550(12) 0.0285(4) Uani 1 1 d . . . . .
C23 C 0.3879(2) 0.26976(17) 0.72994(12) 0.0310(4) Uani 1 1 d . . . . .
H23 H 0.512977 0.300993 0.735464 0.037 Uiso 1 1 calc R U . . .
C24 C 0.3099(2) 0.35189(16) 0.68041(13) 0.0312(4) Uani 1 1 d . . . . .
C25 C 0.3442(3) 0.04969(19) 0.68028(15) 0.0390(4) Uani 1 1 d . . . . .
H25A H 0.391(3) 0.035(2) 0.7422(17) 0.047 Uiso 1 1 d . U . . .
H25B H 0.302(3) -0.019(2) 0.6301(17) 0.047 Uiso 1 1 d . U . . .
C31 C 0.4248(2) 0.36774(18) 0.89550(12) 0.0359(4) Uani 1 1 d . . . . .
C32 C 0.3374(2) 0.25934(18) 0.82540(12) 0.0338(4) Uani 1 1 d . . . . .
H32 H 0.370754 0.190477 0.846676 0.041 Uiso 1 1 calc R U . . .
C33 C 0.1545(2) 0.24028(17) 0.83618(12) 0.0328(4) Uani 1 1 d . . . . .
C34 C 0.1447(2) 0.32140(17) 0.90982(12) 0.0333(4) Uani 1 1 d . . . . .
C35 C -0.0057(3) 0.32359(18) 0.93941(14) 0.0394(4) Uani 1 1 d . . . . .
H35 H -0.009718 0.377227 0.991017 0.047 Uiso 1 1 calc R U . . .
C36 C -0.1514(3) 0.24453(19) 0.89106(16) 0.0433(5) Uani 1 1 d . . . . .
H36 H -0.257088 0.244434 0.909651 0.052 Uiso 1 1 calc R U . . .
C37 C -0.1451(3) 0.1657(2) 0.81606(15) 0.0449(5) Uani 1 1 d . . . . .
H37 H -0.246316 0.113599 0.783090 0.054 Uiso 1 1 calc R U . . .
C38 C 0.0087(3) 0.16254(19) 0.78878(14) 0.0392(4) Uani 1 1 d . . . . .
H38 H 0.013105 0.107503 0.738170 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 0.0181 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'
S S 0.3331 0.5567 '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
O2 S O1 120.56(8) . . ?
O2 S N1 105.82(8) . . ?
O1 S N1 105.59(7) . . ?
O2 S C1 108.04(8) . . ?
O1 S C1 107.59(9) . . ?
N1 S C1 108.81(8) . . ?
C24 O3 C21 111.85(13) . . ?
C21 N1 C11 118.71(13) . . ?
C21 N1 S 119.87(11) . . ?
C11 N1 S 119.08(11) . . ?
C31 N2 C34 111.57(16) . . ?
C2 C1 C6 120.95(18) . . ?
C2 C1 S 119.61(15) . . ?
C6 C1 S 119.44(15) . . ?
C1 C2 C3 119.0(2) . . ?
C2 C3 C4 121.0(2) . . ?
C5 C4 C3 118.89(19) . . ?
C5 C4 C7 120.0(2) . . ?
C3 C4 C7 121.1(2) . . ?
C4 C5 C6 121.0(2) . . ?
C1 C6 C5 119.1(2) . . ?
C16 C11 C12 120.74(16) . . ?
C16 C11 N1 118.40(15) . . ?
C12 C11 N1 120.82(15) . . ?
C13 C12 C11 119.64(17) . . ?
C12 C13 C14 120.05(18) . . ?
C15 C14 C13 120.03(18) . . ?
C14 C15 C16 120.33(18) . . ?
C11 C16 C15 119.20(17) . . ?
N1 C21 O3 110.81(13) . . ?
N1 C21 C22 112.26(14) . . ?
O3 C21 C22 105.20(13) . . ?
C25 C22 C23 128.45(18) . . ?
C25 C22 C21 123.45(18) . . ?
C23 C22 C21 108.10(14) . . ?
C22 C23 C24 103.27(14) . . ?
C22 C23 C32 114.24(16) . . ?
C24 C23 C32 112.76(15) . . ?
O4 C24 O3 121.67(18) . . ?
O4 C24 C23 127.67(18) . . ?
O3 C24 C23 110.66(15) . . ?
O5 C31 N2 126.19(18) . . ?
O5 C31 C32 125.75(17) . . ?
N2 C31 C32 108.04(16) . . ?
C33 C32 C31 102.82(15) . . ?
C33 C32 C23 117.97(15) . . ?
C31 C32 C23 113.94(16) . . ?
C38 C33 C34 119.35(18) . . ?
C38 C33 C32 132.56(18) . . ?
C34 C33 C32 108.09(16) . . ?
C35 C34 C33 122.27(19) . . ?
C35 C34 N2 128.63(18) . . ?
C33 C34 N2 109.10(17) . . ?
C34 C35 C36 117.63(19) . . ?
C37 C36 C35 121.0(2) . . ?
C36 C37 C38 120.5(2) . . ?
C33 C38 C37 119.18(19) . . ?
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
S O2 1.4280(13) . ?
S O1 1.4307(13) . ?
S N1 1.6534(14) . ?
S C1 1.7592(18) . ?
O3 C24 1.360(2) . ?
O3 C21 1.456(2) . ?
O4 C24 1.196(2) . ?
O5 C31 1.230(2) . ?
N1 C21 1.443(2) . ?
N1 C11 1.444(2) . ?
N2 C31 1.359(3) . ?
N2 C34 1.409(3) . ?
C1 C2 1.381(3) . ?
C1 C6 1.385(3) . ?
C2 C3 1.388(3) . ?
C3 C4 1.390(3) . ?
C4 C5 1.378(3) . ?
C4 C7 1.509(3) . ?
C5 C6 1.389(3) . ?
C11 C16 1.383(2) . ?
C11 C12 1.386(2) . ?
C12 C13 1.381(3) . ?
C13 C14 1.386(3) . ?
C14 C15 1.382(3) . ?
C15 C16 1.388(3) . ?
C21 C22 1.510(2) . ?
C22 C25 1.316(3) . ?
C22 C23 1.503(3) . ?
C23 C24 1.520(3) . ?
C23 C32 1.528(3) . ?
C31 C32 1.520(3) . ?
C32 C33 1.509(3) . ?
C33 C38 1.379(3) . ?
C33 C34 1.399(3) . ?
C34 C35 1.378(3) . ?
C35 C36 1.390(3) . ?
C36 C37 1.388(3) . ?
C37 C38 1.394(3) . ?
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
O2 S N1 C21 -161.00(12) . . . . ?
O1 S N1 C21 -32.13(14) . . . . ?
C1 S N1 C21 83.12(14) . . . . ?
O2 S N1 C11 36.61(14) . . . . ?
O1 S N1 C11 165.48(12) . . . . ?
C1 S N1 C11 -79.27(14) . . . . ?
O2 S C1 C2 158.74(16) . . . . ?
O1 S C1 C2 27.12(18) . . . . ?
N1 S C1 C2 -86.82(17) . . . . ?
O2 S C1 C6 -21.24(19) . . . . ?
O1 S C1 C6 -152.86(16) . . . . ?
N1 S C1 C6 93.20(17) . . . . ?
C6 C1 C2 C3 1.1(3) . . . . ?
S C1 C2 C3 -178.88(18) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C2 C3 C4 C7 179.2(3) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C7 C4 C5 C6 -179.2(2) . . . . ?
C2 C1 C6 C5 -1.2(3) . . . . ?
S C1 C6 C5 178.83(17) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C21 N1 C11 C16 95.97(19) . . . . ?
S N1 C11 C16 -101.44(17) . . . . ?
C21 N1 C11 C12 -81.8(2) . . . . ?
S N1 C11 C12 80.83(19) . . . . ?
C16 C11 C12 C13 -0.1(3) . . . . ?
N1 C11 C12 C13 177.57(17) . . . . ?
C11 C12 C13 C14 -0.6(3) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C12 C11 C16 C15 0.7(3) . . . . ?
N1 C11 C16 C15 -177.01(16) . . . . ?
C14 C15 C16 C11 -0.7(3) . . . . ?
C11 N1 C21 O3 63.68(18) . . . . ?
S N1 C21 O3 -98.78(14) . . . . ?
C11 N1 C21 C22 -53.63(19) . . . . ?
S N1 C21 C22 143.92(13) . . . . ?
C24 O3 C21 N1 -116.01(15) . . . . ?
C24 O3 C21 C22 5.55(17) . . . . ?
N1 C21 C22 C25 -69.7(2) . . . . ?
O3 C21 C22 C25 169.66(17) . . . . ?
N1 C21 C22 C23 111.31(15) . . . . ?
O3 C21 C22 C23 -9.29(17) . . . . ?
C25 C22 C23 C24 -169.60(19) . . . . ?
C21 C22 C23 C24 9.29(18) . . . . ?
C25 C22 C23 C32 -46.8(3) . . . . ?
C21 C22 C23 C32 132.11(16) . . . . ?
C21 O3 C24 O4 -179.34(16) . . . . ?
C21 O3 C24 C23 0.38(19) . . . . ?
C22 C23 C24 O4 173.59(19) . . . . ?
C32 C23 C24 O4 49.8(3) . . . . ?
C22 C23 C24 O3 -6.12(19) . . . . ?
C32 C23 C24 O3 -129.93(16) . . . . ?
C34 N2 C31 O5 176.7(2) . . . . ?
C34 N2 C31 C32 -5.0(2) . . . . ?
O5 C31 C32 C33 -175.5(2) . . . . ?
N2 C31 C32 C33 6.2(2) . . . . ?
O5 C31 C32 C23 -46.7(3) . . . . ?
N2 C31 C32 C23 135.04(17) . . . . ?
C22 C23 C32 C33 -71.6(2) . . . . ?
C24 C23 C32 C33 45.9(2) . . . . ?
C22 C23 C32 C31 167.70(15) . . . . ?
C24 C23 C32 C31 -74.8(2) . . . . ?
C31 C32 C33 C38 174.5(2) . . . . ?
C23 C32 C33 C38 48.2(3) . . . . ?
C31 C32 C33 C34 -5.3(2) . . . . ?
C23 C32 C33 C34 -131.56(18) . . . . ?
C38 C33 C34 C35 2.6(3) . . . . ?
C32 C33 C34 C35 -177.53(18) . . . . ?
C38 C33 C34 N2 -177.20(18) . . . . ?
C32 C33 C34 N2 2.6(2) . . . . ?
C31 N2 C34 C35 -178.3(2) . . . . ?
C31 N2 C34 C33 1.6(2) . . . . ?
C33 C34 C35 C36 -2.5(3) . . . . ?
N2 C34 C35 C36 177.34(19) . . . . ?
C34 C35 C36 C37 0.4(3) . . . . ?
C35 C36 C37 C38 1.4(3) . . . . ?
C34 C33 C38 C37 -0.7(3) . . . . ?
C32 C33 C38 C37 179.5(2) . . . . ?
C36 C37 C38 C33 -1.2(3) . . . . ?
