#------------------------------------------------------------------------------
#$Date: 2021-09-06 12:34:03 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268585 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/85/7128548.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_7128548
loop_
_publ_author_name
'Xiong, Qian'
'Luo, Qiliang'
'Zhang, Tinghui'
'Dong, Shunxi'
'Liu, Xiaohua'
'Feng, Xiaoming'
_publ_section_title
;
 Catalytic asymmetric multicomponent reactions of isocyanide,
 isothiocyanate and alkylidene malonates.
;
_journal_issue                   59
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7288
_journal_page_last               7291
_journal_paper_doi               10.1039/d1cc02939h
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H22 N2 O4 S'
_chemical_formula_sum            'C18 H22 N2 O4 S'
_chemical_formula_weight         362.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-04-15 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4981(5)
_cell_length_b                   17.3226(8)
_cell_length_c                   8.4593(4)
_cell_measurement_reflns_used    9992
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.34
_cell_measurement_theta_min      2.68
_cell_volume                     1831.43(14)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            43777
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.430
_diffrn_reflns_theta_min         2.680
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_correction_T_min  0.8978
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EAC, PE'
_exptl_crystal_size_max          0.763
_exptl_crystal_size_mid          0.545
_exptl_crystal_size_min          0.284
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
; 
 Flack x determined using 1264 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.002(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3366
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0308
_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)+(0.0343P)²+0.3686P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0678
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3139
_reflns_number_total             3366
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02939h2.cif
_cod_data_source_block           xiq005
_cod_depositor_comments
'Adding full bibliography for 7128547--7128548.cif.'
_cod_original_cell_volume        1831.44(14)
_cod_database_code               7128548
_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   0.862
_shelx_estimated_absorpt_t_max   0.945
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -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 0.59917(4) 0.72702(4) 0.23863(8) 0.03742(17) Uani 1 1 d . . . . .
O1 O 0.39409(15) 0.60628(10) 0.17072(19) 0.0369(4) Uani 1 1 d . . . . .
O2 O 0.37741(12) 0.55950(8) 0.41642(19) 0.0278(4) Uani 1 1 d . . . . .
O3 O 0.53757(11) 0.65854(9) 0.5830(2) 0.0313(4) Uani 1 1 d . . . . .
O4 O 0.38167(12) 0.70463(10) 0.66917(18) 0.0351(4) Uani 1 1 d . . . . .
N1 N 0.42089(12) 0.81122(10) 0.2385(2) 0.0258(4) Uani 1 1 d . . . . .
N2 N 0.24662(13) 0.85956(9) 0.2605(2) 0.0236(4) Uani 1 1 d D . . . .
H2N H 0.1860(16) 0.8497(12) 0.300(3) 0.025(6) Uiso 1 1 d D . . . .
C1 C 0.32030(15) 0.80675(11) 0.2887(2) 0.0207(4) Uani 1 1 d . . . . .
C2 C 0.29332(15) 0.73694(11) 0.3873(2) 0.0200(4) Uani 1 1 d . . . . .
H2 H 0.277440 0.755091 0.497003 0.024 Uiso 1 1 calc R U . . .
C3 C 0.40380(15) 0.69423(12) 0.3908(2) 0.0211(4) Uani 1 1 d . . . . .
C4 C 0.47486(16) 0.74740(12) 0.2869(3) 0.0248(5) Uani 1 1 d . . . . .
C5 C 0.39340(16) 0.61540(13) 0.3107(3) 0.0242(5) Uani 1 1 d . . . . .
C6 C 0.3531(2) 0.48414(13) 0.3517(3) 0.0378(6) Uani 1 1 d . . . . .
H6A H 0.365869 0.444567 0.432348 0.057 Uiso 1 1 calc R U . . .
H6B H 0.398956 0.474273 0.260014 0.057 Uiso 1 1 calc R U . . .
H6C H 0.277855 0.482555 0.319085 0.057 Uiso 1 1 calc R U . . .
C7 C 0.44994(16) 0.68370(12) 0.5570(3) 0.0225(4) Uani 1 1 d . . . . .
C8 C 0.4148(2) 0.69269(17) 0.8315(3) 0.0423(6) Uani 1 1 d . . . . .
H8A H 0.358932 0.711670 0.902947 0.063 Uiso 1 1 calc R U . . .
H8B H 0.481446 0.720846 0.851252 0.063 Uiso 1 1 calc R U . . .
H8C H 0.426301 0.637470 0.850078 0.063 Uiso 1 1 calc R U . . .
C9 C 0.25870(17) 0.93168(12) 0.1665(3) 0.0265(5) Uani 1 1 d . . . . .
C10 C 0.2944(2) 0.91213(16) 0.0010(3) 0.0406(6) Uani 1 1 d . . . . .
H10A H 0.240733 0.879112 -0.049505 0.061 Uiso 1 1 calc R U . . .
H10B H 0.363031 0.884816 0.005309 0.061 Uiso 1 1 calc R U . . .
H10C H 0.302739 0.959772 -0.060225 0.061 Uiso 1 1 calc R U . . .
C11 C 0.1488(2) 0.96917(16) 0.1598(4) 0.0475(7) Uani 1 1 d . . . . .
H11A H 0.098068 0.933791 0.109171 0.071 Uiso 1 1 calc R U . . .
H11B H 0.152937 1.017104 0.098620 0.071 Uiso 1 1 calc R U . . .
H11C H 0.124409 0.980760 0.267361 0.071 Uiso 1 1 calc R U . . .
C12 C 0.3387(2) 0.98440(14) 0.2481(4) 0.0527(7) Uani 1 1 d . . . . .
H12A H 0.315329 0.994164 0.356864 0.079 Uiso 1 1 calc R U . . .
H12B H 0.343256 1.033420 0.190657 0.079 Uiso 1 1 calc R U . . .
H12C H 0.409215 0.959618 0.249420 0.079 Uiso 1 1 calc R U . . .
C21 C 0.19861(15) 0.68939(11) 0.3312(3) 0.0232(5) Uani 1 1 d . . . . .
C22 C 0.16862(18) 0.68565(13) 0.1736(3) 0.0317(5) Uani 1 1 d . . . . .
H22 H 0.207292 0.714045 0.096370 0.038 Uiso 1 1 calc R U . . .
C23 C 0.0820(2) 0.64041(14) 0.1286(4) 0.0460(7) Uani 1 1 d . . . . .
H23 H 0.061399 0.637836 0.020642 0.055 Uiso 1 1 calc R U . . .
C24 C 0.0262(2) 0.59927(15) 0.2410(4) 0.0567(9) Uani 1 1 d . . . . .
H24 H -0.033302 0.568585 0.210227 0.068 Uiso 1 1 calc R U . . .
C25 C 0.0558(2) 0.60234(16) 0.3970(4) 0.0517(8) Uani 1 1 d . . . . .
H25 H 0.017199 0.573490 0.473596 0.062 Uiso 1 1 calc R U . . .
C26 C 0.14186(18) 0.64735(13) 0.4432(3) 0.0336(6) Uani 1 1 d . . . . .
H26 H 0.162079 0.649492 0.551405 0.040 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
C5 O2 C6 115.66(18) . . ?
C7 O4 C8 117.08(17) . . ?
C1 N1 C4 109.02(17) . . ?
C1 N2 C9 127.40(17) . . ?
N2 C1 N1 124.19(19) . . ?
N2 C1 C2 119.99(17) . . ?
N1 C1 C2 115.79(17) . . ?
C1 C2 C21 115.90(17) . . ?
C1 C2 C3 101.08(15) . . ?
C21 C2 C3 115.91(16) . . ?
C5 C3 C7 109.42(16) . . ?
C5 C3 C4 109.12(17) . . ?
C7 C3 C4 112.04(16) . . ?
C5 C3 C2 109.76(16) . . ?
C7 C3 C2 113.93(16) . . ?
C4 C3 C2 102.31(15) . . ?
N1 C4 C3 111.69(16) . . ?
N1 C4 S 124.67(16) . . ?
C3 C4 S 123.62(15) . . ?
O1 C5 O2 124.7(2) . . ?
O1 C5 C3 123.8(2) . . ?
O2 C5 C3 111.35(17) . . ?
O3 C7 O4 123.8(2) . . ?
O3 C7 C3 123.8(2) . . ?
O4 C7 C3 112.47(16) . . ?
N2 C9 C10 109.72(18) . . ?
N2 C9 C12 109.18(19) . . ?
C10 C9 C12 111.2(2) . . ?
N2 C9 C11 106.66(17) . . ?
C10 C9 C11 109.2(2) . . ?
C12 C9 C11 110.8(2) . . ?
C22 C21 C26 119.6(2) . . ?
C22 C21 C2 122.45(19) . . ?
C26 C21 C2 118.0(2) . . ?
C21 C22 C23 120.0(2) . . ?
C24 C23 C22 119.8(3) . . ?
C25 C24 C23 120.4(2) . . ?
C24 C25 C26 120.2(3) . . ?
C25 C26 C21 119.9(2) . . ?
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 C4 1.645(2) . ?
O1 C5 1.195(3) . ?
O2 C5 1.333(3) . ?
O2 C6 1.448(3) . ?
O3 C7 1.199(2) . ?
O4 C7 1.327(3) . ?
O4 C8 1.449(3) . ?
N1 C1 1.329(3) . ?
N1 C4 1.358(3) . ?
N2 C1 1.320(3) . ?
N2 C9 1.488(3) . ?
C1 C2 1.507(3) . ?
C2 C21 1.518(3) . ?
C2 C3 1.567(3) . ?
C3 C5 1.530(3) . ?
C3 C7 1.531(3) . ?
C3 C4 1.552(3) . ?
C9 C10 1.508(4) . ?
C9 C12 1.520(3) . ?
C9 C11 1.521(3) . ?
C21 C22 1.386(3) . ?
C21 C26 1.390(3) . ?
C22 C23 1.389(3) . ?
C23 C24 1.378(4) . ?
C24 C25 1.372(5) . ?
C25 C26 1.385(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
C9 N2 C1 N1 1.8(4) . . . . ?
C9 N2 C1 C2 180.0(2) . . . . ?
C4 N1 C1 N2 -179.6(2) . . . . ?
C4 N1 C1 C2 2.1(3) . . . . ?
N2 C1 C2 C21 55.4(3) . . . . ?
N1 C1 C2 C21 -126.3(2) . . . . ?
N2 C1 C2 C3 -178.47(18) . . . . ?
N1 C1 C2 C3 -0.1(2) . . . . ?
C1 C2 C3 C5 -117.40(17) . . . . ?
C21 C2 C3 C5 8.8(2) . . . . ?
C1 C2 C3 C7 119.51(18) . . . . ?
C21 C2 C3 C7 -114.3(2) . . . . ?
C1 C2 C3 C4 -1.64(19) . . . . ?
C21 C2 C3 C4 124.52(18) . . . . ?
C1 N1 C4 C3 -3.3(2) . . . . ?
C1 N1 C4 S 175.24(17) . . . . ?
C5 C3 C4 N1 119.29(19) . . . . ?
C7 C3 C4 N1 -119.38(19) . . . . ?
C2 C3 C4 N1 3.1(2) . . . . ?
C5 C3 C4 S -59.2(2) . . . . ?
C7 C3 C4 S 62.1(2) . . . . ?
C2 C3 C4 S -175.46(15) . . . . ?
C6 O2 C5 O1 -3.9(3) . . . . ?
C6 O2 C5 C3 172.51(18) . . . . ?
C7 C3 C5 O1 -154.5(2) . . . . ?
C4 C3 C5 O1 -31.5(3) . . . . ?
C2 C3 C5 O1 79.8(3) . . . . ?
C7 C3 C5 O2 29.1(2) . . . . ?
C4 C3 C5 O2 152.04(16) . . . . ?
C2 C3 C5 O2 -96.58(19) . . . . ?
C8 O4 C7 O3 -2.8(3) . . . . ?
C8 O4 C7 C3 176.4(2) . . . . ?
C5 C3 C7 O3 63.5(3) . . . . ?
C4 C3 C7 O3 -57.7(3) . . . . ?
C2 C3 C7 O3 -173.26(19) . . . . ?
C5 C3 C7 O4 -115.77(19) . . . . ?
C4 C3 C7 O4 123.07(19) . . . . ?
C2 C3 C7 O4 7.5(2) . . . . ?
C1 N2 C9 C10 57.7(3) . . . . ?
C1 N2 C9 C12 -64.4(3) . . . . ?
C1 N2 C9 C11 175.8(2) . . . . ?
C1 C2 C21 C22 28.3(3) . . . . ?
C3 C2 C21 C22 -90.0(2) . . . . ?
C1 C2 C21 C26 -152.87(18) . . . . ?
C3 C2 C21 C26 88.9(2) . . . . ?
C26 C21 C22 C23 0.3(3) . . . . ?
C2 C21 C22 C23 179.2(2) . . . . ?
C21 C22 C23 C24 0.0(4) . . . . ?
C22 C23 C24 C25 -0.4(4) . . . . ?
C23 C24 C25 C26 0.5(5) . . . . ?
C24 C25 C26 C21 -0.2(4) . . . . ?
C22 C21 C26 C25 -0.2(3) . . . . ?
C2 C21 C26 C25 -179.1(2) . . . . ?
