#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/78/7127826.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_7127826
loop_
_publ_author_name
'Mu, Qiu-Qi'
'Nie, Yi-Xue'
'Li, Hang'
'Bai, Xing-Feng'
'Liu, Xue-Wei'
'Xu, Zheng'
'Xu, Li-Wen'
_publ_section_title
;
 Catalytic asymmetric oxidative carbonylation-induced kinetic resolution
 of sterically hindered benzylamines to chiral isoindolinones.
;
_journal_issue                   14
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1778
_journal_page_last               1781
_journal_paper_doi               10.1039/d0cc07218d
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C21 H23 N O4 S'
_chemical_formula_sum            'C21 H23 N O4 S'
_chemical_formula_weight         385.46
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-10 deposited with the CCDC.	2021-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                77.459(2)
_cell_angle_beta                 83.636(2)
_cell_angle_gamma                81.818(2)
_cell_formula_units_Z            2
_cell_length_a                   6.8902(4)
_cell_length_b                   11.3752(7)
_cell_length_c                   12.5546(8)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      70.71
_cell_measurement_theta_min      3.62
_cell_volume                     947.48(10)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16811
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.702
_diffrn_reflns_theta_min         3.619
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.744
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1343 before and 0.0446 after correction. The Ratio of minimum to maximum transmission is 0.7276. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3367
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0369
_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)+(0.0518P)²+0.2688P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1019
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3246
_reflns_number_total             3367
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc07218d2.cif
_cod_data_source_block           cu190930c
_cod_depositor_comments          'Adding full bibliography for 7127826.cif.'
_cod_database_code               7127826
_shelx_shelxl_version_number     2014/7
_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_max   0.722
_shelx_estimated_absorpt_t_min   0.670
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
S1 S 0.56626(6) 0.55149(3) 0.83656(3) 0.04263(14) Uani 1 1 d . . . . .
O1 O 0.89176(18) 0.56922(13) 0.64963(11) 0.0621(3) Uani 1 1 d . . . . .
O2 O 0.69167(19) 0.43957(10) 0.84757(10) 0.0569(3) Uani 1 1 d . . . . .
O3 O 0.36400(17) 0.55336(11) 0.87681(9) 0.0535(3) Uani 1 1 d . . . . .
O4 O 0.8897(2) 0.86546(12) 1.06799(12) 0.0656(4) Uani 1 1 d . . . . .
N1 N 0.56055(18) 0.61156(11) 0.70362(10) 0.0409(3) Uani 1 1 d . . . . .
C1 C 0.7238(2) 0.60080(14) 0.62738(13) 0.0448(3) Uani 1 1 d . . . . .
C2 C 0.6427(3) 0.63530(13) 0.51960(13) 0.0464(4) Uani 1 1 d . . . . .
C3 C 0.7410(3) 0.62914(16) 0.41800(15) 0.0617(5) Uani 1 1 d . . . . .
H3 H 0.8760 0.6062 0.4104 0.074 Uiso 1 1 calc R . . . .
C4 C 0.6299(4) 0.65856(17) 0.32839(15) 0.0743(7) Uani 1 1 d . . . . .
H4 H 0.6911 0.6564 0.2589 0.089 Uiso 1 1 calc R . . . .
C5 C 0.4301(4) 0.69096(17) 0.34119(16) 0.0752(7) Uani 1 1 d . . . . .
H5 H 0.3587 0.7097 0.2798 0.090 Uiso 1 1 calc R . . . .
C6 C 0.3317(3) 0.69661(16) 0.44256(15) 0.0620(5) Uani 1 1 d . . . . .
H6 H 0.1964 0.7183 0.4500 0.074 Uiso 1 1 calc R . . . .
C7 C 0.4426(3) 0.66861(13) 0.53310(13) 0.0452(4) Uani 1 1 d . . . . .
C8 C 0.3749(2) 0.66502(12) 0.65182(12) 0.0409(3) Uani 1 1 d . . . . .
H8 H 0.2752 0.6092 0.6754 0.049 Uiso 1 1 calc R . . . .
C9 C 0.6737(2) 0.65063(13) 0.89511(12) 0.0420(3) Uani 1 1 d . . . . .
C10 C 0.5527(3) 0.74172(16) 0.93625(16) 0.0567(4) Uani 1 1 d . . . . .
H10 H 0.4191 0.7548 0.9261 0.068 Uiso 1 1 calc R . . . .
C11 C 0.6316(3) 0.81246(17) 0.99194(17) 0.0613(5) Uani 1 1 d . . . . .
H11 H 0.5511 0.8743 1.0187 0.074 Uiso 1 1 calc R . . . .
C12 C 0.8291(3) 0.79251(14) 1.00859(13) 0.0486(4) Uani 1 1 d . . . . .
C13 C 0.9508(3) 0.70190(15) 0.96719(14) 0.0494(4) Uani 1 1 d . . . . .
H13 H 1.0843 0.6887 0.9778 0.059 Uiso 1 1 calc R . . . .
C14 C 0.8717(2) 0.63131(14) 0.90993(13) 0.0462(4) Uani 1 1 d . . . . .
H14 H 0.9524 0.5708 0.8815 0.055 Uiso 1 1 calc R . . . .
C15 C 1.0911(3) 0.8514(2) 1.0858(2) 0.0835(7) Uani 1 1 d . . . . .
H15A H 1.1674 0.8692 1.0167 0.125 Uiso 1 1 calc GR . . . .
H15B H 1.1303 0.7694 1.1220 0.125 Uiso 1 1 calc GR . . . .
H15C H 1.1125 0.9060 1.1306 0.125 Uiso 1 1 calc GR . . . .
C16 C 0.2966(2) 0.78886(13) 0.68156(13) 0.0424(3) Uani 1 1 d . . . . .
H16 H 0.2757 0.7745 0.7616 0.051 Uiso 1 1 calc R . . . .
C17 C 0.0984(3) 0.84021(15) 0.63775(17) 0.0575(4) Uani 1 1 d . . . . .
H17A H 0.0065 0.7808 0.6622 0.069 Uiso 1 1 calc R . . . .
H17B H 0.1127 0.8570 0.5583 0.069 Uiso 1 1 calc R . . . .
C18 C 0.0173(3) 0.95662(17) 0.6774(2) 0.0682(5) Uani 1 1 d . . . . .
H18A H -0.1060 0.9898 0.6457 0.082 Uiso 1 1 calc R . . . .
H18B H -0.0088 0.9383 0.7564 0.082 Uiso 1 1 calc R . . . .
C19 C 0.1612(3) 1.04999(16) 0.64564(19) 0.0696(5) Uani 1 1 d . . . . .
H19A H 0.1743 1.0759 0.5666 0.084 Uiso 1 1 calc R . . . .
H19B H 0.1100 1.1205 0.6765 0.084 Uiso 1 1 calc R . . . .
C20 C 0.3607(3) 0.99979(16) 0.68567(19) 0.0652(5) Uani 1 1 d . . . . .
H20A H 0.3507 0.9843 0.7651 0.078 Uiso 1 1 calc R . . . .
H20B H 0.4514 1.0596 0.6588 0.078 Uiso 1 1 calc R . . . .
C21 C 0.4419(3) 0.88236(14) 0.64735(16) 0.0522(4) Uani 1 1 d . . . . .
H21A H 0.4670 0.8994 0.5683 0.063 Uiso 1 1 calc R . . . .
H21B H 0.5656 0.8497 0.6788 0.063 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 0.0181 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 S1 O3 120.09(8) . . ?
O2 S1 N1 107.77(7) . . ?
O2 S1 C9 108.16(7) . . ?
O3 S1 N1 104.31(7) . . ?
O3 S1 C9 108.68(7) . . ?
N1 S1 C9 107.13(7) . . ?
C12 O4 C15 118.15(14) . . ?
C1 N1 S1 123.21(11) . . ?
C1 N1 C8 113.26(12) . . ?
C8 N1 S1 122.90(10) . . ?
O1 C1 N1 125.36(15) . . ?
O1 C1 C2 129.60(15) . . ?
N1 C1 C2 105.04(13) . . ?
C3 C2 C1 127.82(17) . . ?
C7 C2 C1 109.60(14) . . ?
C7 C2 C3 122.44(17) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 C2 117.3(2) . . ?
C4 C3 H3 121.3 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.64(19) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 118.9 . . ?
C4 C5 C6 122.10(19) . . ?
C6 C5 H5 118.9 . . ?
C5 C6 H6 121.2 . . ?
C5 C6 C7 117.7(2) . . ?
C7 C6 H6 121.2 . . ?
C2 C7 C6 119.80(17) . . ?
C2 C7 C8 111.14(13) . . ?
C6 C7 C8 129.03(17) . . ?
N1 C8 C7 100.40(12) . . ?
N1 C8 H8 109.7 . . ?
N1 C8 C16 111.34(12) . . ?
C7 C8 H8 109.7 . . ?
C7 C8 C16 115.61(12) . . ?
C16 C8 H8 109.7 . . ?
C10 C9 S1 118.81(13) . . ?
C14 C9 S1 120.62(11) . . ?
C14 C9 C10 120.25(15) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.61(16) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.51(15) . . ?
C12 C11 H11 119.7 . . ?
O4 C12 C11 115.41(14) . . ?
O4 C12 C13 124.49(16) . . ?
C11 C12 C13 120.09(15) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.41(16) . . ?
C14 C13 H13 120.3 . . ?
C9 C14 C13 120.12(14) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C16 H16 106.7 . . ?
C17 C16 C8 112.33(13) . . ?
C17 C16 H16 106.7 . . ?
C17 C16 C21 110.47(13) . . ?
C21 C16 C8 113.51(13) . . ?
C21 C16 H16 106.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 C18 110.80(16) . . ?
H17A C17 H17B 108.1 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C17 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 C17 111.22(17) . . ?
C19 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
C18 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C20 C19 C18 111.64(16) . . ?
C20 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C19 C20 H20A 109.3 . . ?
C19 C20 H20B 109.3 . . ?
C19 C20 C21 111.77(16) . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
C16 C21 C20 110.76(15) . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
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
S1 O2 1.4225(11) . ?
S1 O3 1.4276(12) . ?
S1 N1 1.6631(12) . ?
S1 C9 1.7545(16) . ?
O1 C1 1.207(2) . ?
O4 C12 1.362(2) . ?
O4 C15 1.411(3) . ?
N1 C1 1.403(2) . ?
N1 C8 1.4902(19) . ?
C1 C2 1.474(2) . ?
C2 C3 1.387(2) . ?
C2 C7 1.379(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.394(2) . ?
C7 C8 1.505(2) . ?
C8 H8 0.9800 . ?
C8 C16 1.543(2) . ?
C9 C10 1.388(2) . ?
C9 C14 1.377(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.373(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(3) . ?
C12 C13 1.388(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(2) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 0.9800 . ?
C16 C17 1.519(2) . ?
C16 C21 1.525(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.525(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.516(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.508(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.528(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168352525
