#------------------------------------------------------------------------------
#$Date: 2024-10-06 09:16:33 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295148 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/37/7133718.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_7133718
loop_
_publ_author_name
'Wang, Zhan-Yong'
'Ma, Guoyang'
'Xu, Yaoyao'
'Wang, Qingqing'
'Zhang, Mengru'
'Ma, Xueji'
'Ma, Chenyang'
'Sun, Aili'
'Xia, Ran'
'Liu, Hongxin'
_publ_section_title
;
 One-pot synthesis of functionalized dihydropyridin-2-ones via
 carbene-catalyzed base-controlled [3+3] annulation reaction.
;
_journal_issue                   80
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11327
_journal_page_last               11330
_journal_paper_doi               10.1039/d4cc03521f
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C31 H25 N O4 S'
_chemical_formula_sum            'C31 H25 N O4 S'
_chemical_formula_weight         507.58
_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             2023-10-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-10-13 deposited with the CCDC.	2024-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                91.730(4)
_cell_angle_beta                 99.279(4)
_cell_angle_gamma                92.540(3)
_cell_formula_units_Z            2
_cell_length_a                   8.671(2)
_cell_length_b                   10.576(2)
_cell_length_c                   14.370(3)
_cell_measurement_reflns_used    3526
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.287
_cell_measurement_theta_min      2.361
_cell_volume                     1298.3(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7874
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.447
_diffrn_reflns_theta_min         2.875
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7034
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0448 before and 0.0253 after correction.
The Ratio of minimum to maximum transmission is 0.9434.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5627
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0486
_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)+(0.0626P)²+0.3646P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1352
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4216
_reflns_number_total             5627
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc03521f2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7133718.cif.'
_cod_database_code               7133718
_shelx_shelxl_version_number     2016/6
_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   0.965
_shelx_estimated_absorpt_t_min   0.959
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C20(H20), C30(H30), C17(H17), C26(H26), C29(H29), C13(H13),
 C21(H21), C22(H22), C23(H23), C5(H5), C27(H27), C4(H4), C16(H16), C14(H14),
 C15(H15), C3(H3), C1(H1), C2(H2)
2.d Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
;
_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 0.52469(6) 0.61515(4) 0.80681(3) 0.04729(15) Uani 1 1 d . . . . .
O1 O 0.65641(17) 0.88665(12) 0.71206(9) 0.0556(4) Uani 1 1 d . . . . .
O3 O 0.46633(16) 0.63537(14) 0.71009(9) 0.0576(4) Uani 1 1 d . . . . .
O4 O 0.50941(19) 0.49171(13) 0.84189(11) 0.0638(4) Uani 1 1 d . . . . .
N1 N 0.71846(18) 0.65703(14) 0.81800(10) 0.0430(3) Uani 1 1 d . . . . .
O2 O 0.7627(2) 0.59707(17) 0.97023(10) 0.0748(5) Uani 1 1 d . . . . .
C18 C 0.6927(2) 0.79004(15) 0.67490(12) 0.0393(4) Uani 1 1 d . . . . .
C10 C 0.7831(2) 0.69539(15) 0.73622(11) 0.0396(4) Uani 1 1 d . . . . .
C19 C 0.6578(2) 0.76483(16) 0.57103(12) 0.0396(4) Uani 1 1 d . . . . .
C11 C 0.9258(2) 0.66172(16) 0.72483(13) 0.0424(4) Uani 1 1 d . . . . .
C12 C 1.0092(2) 0.71307(16) 0.65093(13) 0.0439(4) Uani 1 1 d . . . . .
C25 C 0.4451(2) 0.72471(18) 0.87697(13) 0.0468(4) Uani 1 1 d . . . . .
C6 C 0.9909(2) 0.43983(18) 0.78229(14) 0.0512(5) Uani 1 1 d . . . . .
C9 C 0.8174(3) 0.62562(19) 0.90125(13) 0.0536(5) Uani 1 1 d . . . . .
C24 C 0.6238(3) 0.86499(19) 0.51259(14) 0.0540(5) Uani 1 1 d . . . . .
H24 H 0.623649 0.946539 0.538660 0.065 Uiso 1 1 calc R . . . .
C7 C 1.0187(2) 0.58256(19) 0.79868(14) 0.0512(5) Uani 1 1 d . . . . .
H7 H 1.129683 0.602077 0.796884 0.061 Uiso 1 1 calc R . . . .
C20 C 0.6557(2) 0.64416(18) 0.53103(14) 0.0515(5) Uani 1 1 d . . . . .
H20 H 0.677509 0.575934 0.569524 0.062 Uiso 1 1 calc R . . . .
C30 C 0.4356(3) 0.7008(2) 0.97005(15) 0.0610(5) Uani 1 1 d . . . . .
H30 H 0.473280 0.626919 0.996814 0.073 Uiso 1 1 calc R . . . .
C8 C 0.9874(2) 0.6301(2) 0.89518(14) 0.0585(5) Uani 1 1 d . . . . .
H8A H 1.041127 0.578543 0.943669 0.070 Uiso 1 1 calc R . . . .
H8B H 1.029572 0.716594 0.907162 0.070 Uiso 1 1 calc R . . . .
C17 C 1.0305(3) 0.84251(18) 0.64237(16) 0.0568(5) Uani 1 1 d . . . . .
H17 H 0.988890 0.897830 0.682202 0.068 Uiso 1 1 calc R . . . .
C26 C 0.3857(3) 0.8324(2) 0.83651(16) 0.0614(5) Uani 1 1 d . . . . .
H26 H 0.390257 0.847453 0.773565 0.074 Uiso 1 1 calc R . . . .
C29 C 0.3690(3) 0.7886(2) 1.02254(17) 0.0708(6) Uani 1 1 d . . . . .
H29 H 0.362473 0.772984 1.085168 0.085 Uiso 1 1 calc R . . . .
C13 C 1.0756(3) 0.6333(2) 0.59271(17) 0.0644(6) Uani 1 1 d . . . . .
H13 H 1.066026 0.546133 0.598803 0.077 Uiso 1 1 calc R . . . .
C21 C 0.6216(3) 0.6241(2) 0.43439(15) 0.0629(6) Uani 1 1 d . . . . .
H21 H 0.620240 0.542617 0.407985 0.075 Uiso 1 1 calc R . . . .
C28 C 0.3120(3) 0.8985(2) 0.98473(18) 0.0648(6) Uani 1 1 d . . . . .
C22 C 0.5896(3) 0.7247(3) 0.37723(15) 0.0680(6) Uani 1 1 d . . . . .
H22 H 0.567539 0.711177 0.312098 0.082 Uiso 1 1 calc R . . . .
C23 C 0.5900(3) 0.8448(2) 0.41577(15) 0.0666(6) Uani 1 1 d . . . . .
H23 H 0.567603 0.912631 0.376927 0.080 Uiso 1 1 calc R . . . .
C5 C 0.8465(3) 0.3809(2) 0.75002(19) 0.0691(6) Uani 1 1 d . . . . .
H5 H 0.760487 0.429736 0.733260 0.083 Uiso 1 1 calc R . . . .
C27 C 0.3191(3) 0.9176(2) 0.8909(2) 0.0717(6) Uani 1 1 d . . . . .
H27 H 0.277855 0.989885 0.863516 0.086 Uiso 1 1 calc R . . . .
C4 C 0.8276(4) 0.2507(2) 0.7422(2) 0.0810(8) Uani 1 1 d . . . . .
H4 H 0.728769 0.212269 0.721960 0.097 Uiso 1 1 calc R . . . .
C16 C 1.1124(3) 0.8904(2) 0.57562(19) 0.0719(7) Uani 1 1 d . . . . .
H16 H 1.125366 0.977568 0.570413 0.086 Uiso 1 1 calc R . . . .
C14 C 1.1561(3) 0.6820(3) 0.5255(2) 0.0822(8) Uani 1 1 d . . . . .
H14 H 1.198116 0.627186 0.485461 0.099 Uiso 1 1 calc R . . . .
C15 C 1.1748(3) 0.8098(3) 0.5170(2) 0.0808(8) Uani 1 1 d . . . . .
H15 H 1.229634 0.841944 0.471665 0.097 Uiso 1 1 calc R . . . .
C3 C 0.9531(5) 0.1786(3) 0.7639(2) 0.0982(10) Uani 1 1 d . . . . .
H3 H 0.941124 0.090726 0.758041 0.118 Uiso 1 1 calc R . . . .
C1 C 1.1176(3) 0.3660(3) 0.8048(2) 0.0846(8) Uani 1 1 d . . . . .
H1 H 1.216201 0.403653 0.826861 0.101 Uiso 1 1 calc R . . . .
C31 C 0.2394(4) 0.9941(3) 1.0433(2) 0.0965(10) Uani 1 1 d . . . . .
H31A H 0.138694 0.961106 1.053395 0.145 Uiso 1 1 calc GR . . . .
H31B H 0.227535 1.071756 1.010590 0.145 Uiso 1 1 calc GR . . . .
H31C H 0.305965 1.009929 1.103099 0.145 Uiso 1 1 calc GR . . . .
C2 C 1.0976(5) 0.2364(3) 0.7945(3) 0.1185(13) Uani 1 1 d . . . . .
H2 H 1.183814 0.187042 0.808638 0.142 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'
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
O3 S1 N1 103.79(8) . . ?
O3 S1 C25 108.75(9) . . ?
O4 S1 O3 119.14(9) . . ?
O4 S1 N1 108.17(9) . . ?
O4 S1 C25 109.90(9) . . ?
N1 S1 C25 106.22(8) . . ?
C10 N1 S1 119.53(11) . . ?
C9 N1 S1 118.20(13) . . ?
C9 N1 C10 120.65(16) . . ?
O1 C18 C10 118.63(15) . . ?
O1 C18 C19 122.19(15) . . ?
C19 C18 C10 119.12(14) . . ?
N1 C10 C18 116.36(15) . . ?
C11 C10 N1 120.08(16) . . ?
C11 C10 C18 122.88(16) . . ?
C24 C19 C18 119.05(16) . . ?
C20 C19 C18 122.07(16) . . ?
C20 C19 C24 118.87(17) . . ?
C10 C11 C12 123.03(16) . . ?
C10 C11 C7 119.35(17) . . ?
C12 C11 C7 116.99(16) . . ?
C17 C12 C11 120.83(17) . . ?
C13 C12 C11 120.72(16) . . ?
C13 C12 C17 118.34(18) . . ?
C30 C25 S1 120.59(16) . . ?
C26 C25 S1 118.66(15) . . ?
C26 C25 C30 120.67(19) . . ?
C5 C6 C7 123.91(18) . . ?
C5 C6 C1 118.6(2) . . ?
C1 C6 C7 117.4(2) . . ?
N1 C9 C8 115.03(17) . . ?
O2 C9 N1 120.2(2) . . ?
O2 C9 C8 124.73(19) . . ?
C19 C24 H24 119.7 . . ?
C23 C24 C19 120.6(2) . . ?
C23 C24 H24 119.7 . . ?
C11 C7 C6 114.99(16) . . ?
C11 C7 H7 106.9 . . ?
C11 C7 C8 107.23(16) . . ?
C6 C7 H7 106.9 . . ?
C6 C7 C8 113.32(17) . . ?
C8 C7 H7 106.9 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.52(19) . . ?
C21 C20 H20 119.7 . . ?
C25 C30 H30 120.6 . . ?
C29 C30 C25 118.8(2) . . ?
C29 C30 H30 120.6 . . ?
C9 C8 C7 112.28(16) . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.9(2) . . ?
C16 C17 H17 119.6 . . ?
C25 C26 H26 120.5 . . ?
C25 C26 C27 118.9(2) . . ?
C27 C26 H26 120.5 . . ?
C30 C29 H29 119.1 . . ?
C28 C29 C30 121.8(2) . . ?
C28 C29 H29 119.1 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 119.9(2) . . ?
C22 C21 H21 120.0 . . ?
C29 C28 C27 117.8(2) . . ?
C29 C28 C31 121.2(2) . . ?
C27 C28 C31 120.9(2) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.3(2) . . ?
C23 C22 H22 119.8 . . ?
C24 C23 H23 120.1 . . ?
C22 C23 C24 119.8(2) . . ?
C22 C23 H23 120.1 . . ?
C6 C5 H5 119.5 . . ?
C6 C5 C4 121.0(2) . . ?
C4 C5 H5 119.5 . . ?
C26 C27 C28 121.9(2) . . ?
C26 C27 H27 119.1 . . ?
C28 C27 H27 119.1 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.7(2) . . ?
C15 C14 H14 119.7 . . ?
C16 C15 H15 120.2 . . ?
C14 C15 C16 119.7(2) . . ?
C14 C15 H15 120.2 . . ?
C4 C3 H3 120.3 . . ?
C4 C3 C2 119.4(3) . . ?
C2 C3 H3 120.3 . . ?
C6 C1 H1 120.2 . . ?
C2 C1 C6 119.7(3) . . ?
C2 C1 H1 120.2 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
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 O3 1.4262(14) . ?
S1 O4 1.4219(15) . ?
S1 N1 1.6993(16) . ?
S1 C25 1.749(2) . ?
O1 C18 1.216(2) . ?
N1 C10 1.442(2) . ?
N1 C9 1.413(2) . ?
O2 C9 1.207(2) . ?
C18 C10 1.514(2) . ?
C18 C19 1.488(2) . ?
C10 C11 1.337(2) . ?
C19 C24 1.384(2) . ?
C19 C20 1.382(2) . ?
C11 C12 1.481(3) . ?
C11 C7 1.521(2) . ?
C12 C17 1.385(3) . ?
C12 C13 1.378(3) . ?
C25 C30 1.384(3) . ?
C25 C26 1.377(3) . ?
C6 C7 1.523(3) . ?
C6 C5 1.377(3) . ?
C6 C1 1.378(3) . ?
C9 C8 1.489(3) . ?
C24 H24 0.9300 . ?
C24 C23 1.383(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.530(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(3) . ?
C30 H30 0.9300 . ?
C30 C29 1.383(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C17 H17 0.9300 . ?
C17 C16 1.378(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.380(3) . ?
C29 H29 0.9300 . ?
C29 C28 1.375(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.374(3) . ?
C28 C27 1.380(3) . ?
C28 C31 1.518(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.370(3) . ?
C23 H23 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.379(3) . ?
C27 H27 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.357(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.369(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.366(4) . ?
C15 H15 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.369(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.374(4) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C2 H2 0.9300 . ?
