#------------------------------------------------------------------------------
#$Date: 2024-02-04 13:22:37 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289381 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/25/7132590.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_7132590
loop_
_publ_author_name
'Tang, Yi'
'Zhang, Rulei'
'Dong, Yujie'
'Yu, Songcheng'
'Wu, Yongjun'
'Xiao, Yumei'
'Guo, Hongchao'
_publ_section_title
;
 4-Vinylbenzodioxinones as a new type of precursor for palladium-catalyzed
 (4+3) cycloaddition of azomethine imines.
;
_journal_issue                   11
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1436
_journal_page_last               1439
_journal_paper_doi               10.1039/d3cc06012h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_sum            'C24 H21 N3 O3 S'
_chemical_formula_weight         431.50
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-05-22 deposited with the CCDC.	2024-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                104.791(2)
_cell_angle_beta                 92.638(2)
_cell_angle_gamma                111.152(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0853(5)
_cell_length_b                   10.9301(7)
_cell_length_c                   13.3531(8)
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.23
_cell_volume                     1051.52(11)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32847
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.550
_diffrn_reflns_theta_min         2.089
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.450
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0404
_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)+(0.0800P)²+0.2282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1269
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4055
_reflns_number_total             4845
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc06012h2.cif
_cod_data_source_block           b221212d_0m_a
_cod_depositor_comments
'Adding full bibliography for 7132590--7132592.cif.'
_cod_database_code               7132590
_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   0.900
_shelx_estimated_absorpt_t_max   0.921
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 0.72436(5) 0.95490(3) 0.66790(3) 0.02952(12) Uani 1 1 d . . . . .
O1 O 0.87335(15) 0.98257(12) 0.74362(9) 0.0439(3) Uani 1 1 d . . . . .
O2 O 0.65729(16) 1.05872(11) 0.66670(9) 0.0409(3) Uani 1 1 d . . . . .
O3 O 0.42787(15) 0.68487(11) 0.84380(8) 0.0363(3) Uani 1 1 d . . . . .
N1 N 0.55163(16) 0.82445(12) 0.68118(10) 0.0312(3) Uani 1 1 d . . . . .
N2 N 0.59393(17) 0.72150(12) 0.70446(9) 0.0299(3) Uani 1 1 d . . . . .
N3 N 0.6127(2) 0.50752(13) 0.63386(10) 0.0388(3) Uani 1 1 d . . . . .
C1 C 0.5780(2) 0.60887(15) 0.62390(11) 0.0335(3) Uani 1 1 d . . . . .
H1 H 0.538698 0.606467 0.556606 0.040 Uiso 1 1 calc R U . . .
C2 C 0.6698(2) 0.51299(15) 0.73700(12) 0.0331(3) Uani 1 1 d . . . . .
C3 C 0.7275(2) 0.41151(18) 0.75088(15) 0.0436(4) Uani 1 1 d . . . . .
H3 H 0.727811 0.343016 0.692953 0.052 Uiso 1 1 calc R U . . .
C4 C 0.7836(3) 0.4127(2) 0.84989(17) 0.0546(5) Uani 1 1 d . . . . .
H4 H 0.821375 0.344620 0.858419 0.066 Uiso 1 1 calc R U . . .
C5 C 0.7847(3) 0.5136(2) 0.93687(16) 0.0622(6) Uani 1 1 d . . . . .
H5 H 0.822516 0.513283 1.003613 0.075 Uiso 1 1 calc R U . . .
C6 C 0.7293(3) 0.6148(2) 0.92410(14) 0.0519(5) Uani 1 1 d . . . . .
H6 H 0.731079 0.683580 0.982494 0.062 Uiso 1 1 calc R U . . .
C7 C 0.6709(2) 0.61491(15) 0.82445(12) 0.0336(3) Uani 1 1 d . . . . .
C8 C 0.6022(2) 0.72117(15) 0.81217(11) 0.0309(3) Uani 1 1 d . . . . .
H8 H 0.682674 0.811660 0.857379 0.037 Uiso 1 1 calc R U . . .
C9 C 0.3590(2) 0.78625(15) 0.86961(12) 0.0329(3) Uani 1 1 d . . . . .
C10 C 0.3094(3) 0.81259(19) 0.96813(13) 0.0456(4) Uani 1 1 d . . . . .
H10 H 0.333618 0.769732 1.015543 0.055 Uiso 1 1 calc R U . . .
C11 C 0.2237(3) 0.9027(2) 0.99629(14) 0.0525(5) Uani 1 1 d . . . . .
H11 H 0.187935 0.918579 1.061968 0.063 Uiso 1 1 calc R U . . .
C12 C 0.1917(3) 0.9683(2) 0.92753(15) 0.0495(4) Uani 1 1 d . . . . .
H12 H 0.134090 1.028804 0.946342 0.059 Uiso 1 1 calc R U . . .
C13 C 0.2452(2) 0.94433(17) 0.82995(14) 0.0405(4) Uani 1 1 d . . . . .
H13 H 0.224374 0.990219 0.784003 0.049 Uiso 1 1 calc R U . . .
C14 C 0.32927(19) 0.85341(15) 0.79907(11) 0.0312(3) Uani 1 1 d . . . . .
C15 C 0.36892(19) 0.82204(16) 0.68801(11) 0.0315(3) Uani 1 1 d . . . . .
H15 H 0.361106 0.894906 0.660259 0.038 Uiso 1 1 calc R U . . .
C16 C 0.2346(2) 0.68857(19) 0.61644(13) 0.0449(4) Uani 1 1 d . . . . .
H16 H 0.257360 0.659936 0.548582 0.054 Uiso 1 1 calc R U . . .
C17 C 0.0898(3) 0.6105(2) 0.64206(18) 0.0663(6) Uani 1 1 d . . . . .
H17A H 0.062436 0.635663 0.709203 0.080 Uiso 1 1 calc R U . . .
H17B H 0.013385 0.529409 0.593300 0.080 Uiso 1 1 calc R U . . .
C18 C 0.76999(19) 0.88942(15) 0.54309(11) 0.0300(3) Uani 1 1 d . . . . .
C19 C 0.8980(2) 0.83306(18) 0.53119(14) 0.0409(4) Uani 1 1 d . . . . .
H19 H 0.969902 0.837333 0.589431 0.049 Uiso 1 1 calc R U . . .
C20 C 0.9178(3) 0.7701(2) 0.43121(16) 0.0500(4) Uani 1 1 d . . . . .
H20 H 1.004384 0.732392 0.422786 0.060 Uiso 1 1 calc R U . . .
C21 C 0.8121(2) 0.76180(17) 0.34351(14) 0.0454(4) Uani 1 1 d . . . . .
C22 C 0.6875(2) 0.82231(18) 0.35785(13) 0.0433(4) Uani 1 1 d . . . . .
H22 H 0.617921 0.820353 0.299560 0.052 Uiso 1 1 calc R U . . .
C23 C 0.6645(2) 0.88508(17) 0.45628(12) 0.0380(3) Uani 1 1 d . . . . .
H23 H 0.579339 0.924197 0.464643 0.046 Uiso 1 1 calc R U . . .
C24 C 0.8284(4) 0.6881(2) 0.23506(17) 0.0722(7) Uani 1 1 d . . . . .
H24A H 0.921304 0.749751 0.208725 0.108 Uiso 1 1 calc R U . . .
H24B H 0.716488 0.656383 0.189698 0.108 Uiso 1 1 calc R U . . .
H24C H 0.857826 0.611254 0.237527 0.108 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'
S S 0.1246 0.1234 '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
O1 S1 O2 120.28(7) . . ?
O1 S1 N1 108.63(7) . . ?
O2 S1 N1 105.36(7) . . ?
O1 S1 C18 108.63(7) . . ?
O2 S1 C18 109.62(7) . . ?
N1 S1 C18 102.90(7) . . ?
C9 O3 C8 117.65(11) . . ?
N2 N1 C15 119.10(11) . . ?
N2 N1 S1 115.08(9) . . ?
C15 N1 S1 124.93(10) . . ?
C1 N2 N1 118.66(12) . . ?
C1 N2 C8 122.43(12) . . ?
N1 N2 C8 116.54(11) . . ?
C1 N3 C2 116.14(13) . . ?
N3 C1 N2 125.31(14) . . ?
N3 C1 H1 117.3 . . ?
N2 C1 H1 117.3 . . ?
C7 C2 C3 119.14(15) . . ?
C7 C2 N3 122.64(13) . . ?
C3 C2 N3 118.21(14) . . ?
C4 C3 C2 120.12(16) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.92(16) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 119.49(17) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 120.46(17) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C6 119.87(15) . . ?
C2 C7 C8 120.22(13) . . ?
C6 C7 C8 119.86(14) . . ?
O3 C8 N2 111.61(12) . . ?
O3 C8 C7 106.85(11) . . ?
N2 C8 C7 108.87(12) . . ?
O3 C8 H8 109.8 . . ?
N2 C8 H8 109.8 . . ?
C7 C8 H8 109.8 . . ?
C10 C9 O3 116.52(14) . . ?
C10 C9 C14 120.57(14) . . ?
O3 C9 C14 122.79(13) . . ?
C9 C10 C11 120.11(17) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.05(16) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 119.74(16) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 121.50(16) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C9 117.98(14) . . ?
C13 C14 C15 118.79(13) . . ?
C9 C14 C15 122.98(13) . . ?
N1 C15 C16 109.30(13) . . ?
N1 C15 C14 113.35(11) . . ?
C16 C15 C14 113.50(13) . . ?
N1 C15 H15 106.7 . . ?
C16 C15 H15 106.7 . . ?
C14 C15 H15 106.7 . . ?
C17 C16 C15 125.10(17) . . ?
C17 C16 H16 117.4 . . ?
C15 C16 H16 117.4 . . ?
C16 C17 H17A 120.0 . . ?
C16 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?
C19 C18 C23 120.68(14) . . ?
C19 C18 S1 120.58(12) . . ?
C23 C18 S1 118.52(11) . . ?
C18 C19 C20 118.88(16) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C21 C20 C19 121.65(16) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C22 118.14(15) . . ?
C20 C21 C24 121.58(18) . . ?
C22 C21 C24 120.28(19) . . ?
C23 C22 C21 121.42(16) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C22 C23 C18 119.19(15) . . ?
C22 C23 H23 120.4 . . ?
C18 C23 H23 120.4 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
S1 O1 1.4260(12) . ?
S1 O2 1.4264(11) . ?
S1 N1 1.6522(13) . ?
S1 C18 1.7504(15) . ?
O3 C9 1.3875(17) . ?
O3 C8 1.4353(18) . ?
N1 N2 1.3880(16) . ?
N1 C15 1.4754(18) . ?
N2 C1 1.3733(18) . ?
N2 C8 1.4378(17) . ?
N3 C1 1.2726(19) . ?
N3 C2 1.412(2) . ?
C1 H1 0.9300 . ?
C2 C7 1.390(2) . ?
C2 C3 1.397(2) . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.392(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.4961(19) . ?
C8 H8 0.9800 . ?
C9 C10 1.383(2) . ?
C9 C14 1.394(2) . ?
C10 C11 1.385(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.511(2) . ?
C15 C16 1.507(2) . ?
C15 H15 0.9800 . ?
C16 C17 1.296(3) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9300 . ?
C17 H17B 0.9300 . ?
C18 C19 1.379(2) . ?
C18 C23 1.387(2) . ?
C19 C20 1.382(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.387(3) . ?
C21 C24 1.504(2) . ?
C22 C23 1.373(2) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
