#------------------------------------------------------------------------------
#$Date: 2021-09-06 11:34:03 +0200 (Mon 06 de Sep de 2021) $
#$Revision: 268585 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/85/7128547.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_7128547
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         'C17 H26 N2 O4 S'
_chemical_formula_sum            'C17 H26 N2 O4 S'
_chemical_formula_weight         354.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-02-01 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                   9.7300(2)
_cell_length_b                   11.7702(3)
_cell_length_c                   16.4807(4)
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      5.28
_cell_volume                     1887.44(8)
_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 0.997
_diffrn_measured_fraction_theta_max 0.996
_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  0.0322
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25366
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.307
_diffrn_reflns_theta_min         5.279
_exptl_absorpt_coefficient_mu    1.712
_exptl_absorpt_correction_T_max  0.7806
_exptl_absorpt_correction_T_min  0.6374
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOAc, PE'
_exptl_crystal_size_max          0.319
_exptl_crystal_size_mid          0.295
_exptl_crystal_size_min          0.272
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
; 
 Flack x determined using 1432 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.043(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3442
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0252
_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)+(0.0390P)²+0.3899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0704
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3401
_reflns_number_total             3442
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02939h2.cif
_cod_data_source_block           xiq003
_cod_depositor_comments
'Adding full bibliography for 7128547--7128548.cif.'
_cod_database_code               7128547
_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   0.611
_shelx_estimated_absorpt_t_max   0.653
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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 0.38852(5) 0.72960(4) 0.39686(3) 0.02551(13) Uani 1 1 d . . . . .
O1 O 0.61952(17) 0.76830(14) 0.23605(8) 0.0324(3) Uani 1 1 d . . . . .
O2 O 0.58527(16) 0.93443(12) 0.29994(8) 0.0278(3) Uani 1 1 d . . . . .
O3 O 0.60112(14) 0.90243(12) 0.49329(8) 0.0247(3) Uani 1 1 d . . . . .
O4 O 0.79193(14) 0.94444(12) 0.42376(8) 0.0223(3) Uani 1 1 d . . . . .
N1 N 0.60538(16) 0.60363(13) 0.43743(9) 0.0188(3) Uani 1 1 d . . . . .
N2 N 0.82177(17) 0.53047(14) 0.46559(10) 0.0192(3) Uani 1 1 d D . . . .
H2N H 0.910(2) 0.546(2) 0.4680(16) 0.032(7) Uiso 1 1 d D . . . .
C1 C 0.74223(18) 0.60719(16) 0.43233(11) 0.0160(4) Uani 1 1 d . . . . .
C2 C 0.80160(18) 0.70881(15) 0.38692(11) 0.0167(4) Uani 1 1 d . . . . .
H2 H 0.867576 0.748548 0.423782 0.020 Uiso 1 1 calc R U . . .
C3 C 0.66937(18) 0.78347(15) 0.37968(10) 0.0160(4) Uani 1 1 d . . . . .
C4 C 0.55312(18) 0.70056(15) 0.40659(11) 0.0175(4) Uani 1 1 d . . . . .
C5 C 0.6255(2) 0.82632(17) 0.29590(11) 0.0203(4) Uani 1 1 d . . . . .
C6 C 0.5187(3) 0.9789(2) 0.22774(15) 0.0447(7) Uani 1 1 d . . . . .
H6A H 0.491369 1.057900 0.237143 0.067 Uiso 1 1 calc R U . . .
H6B H 0.437087 0.933197 0.215456 0.067 Uiso 1 1 calc R U . . .
H6C H 0.582726 0.975437 0.181902 0.067 Uiso 1 1 calc R U . . .
C7 C 0.68064(18) 0.88298(16) 0.43926(11) 0.0166(4) Uani 1 1 d . . . . .
C8 C 0.8143(2) 1.04030(18) 0.47705(14) 0.0293(5) Uani 1 1 d . . . . .
H8A H 0.886024 1.089290 0.454236 0.044 Uiso 1 1 calc R U . . .
H8B H 0.843369 1.012937 0.530535 0.044 Uiso 1 1 calc R U . . .
H8C H 0.728817 1.083607 0.482493 0.044 Uiso 1 1 calc R U . . .
C9 C 0.7776(2) 0.43319(17) 0.51752(13) 0.0229(4) Uani 1 1 d . . . . .
C10 C 0.9090(2) 0.3699(2) 0.54058(18) 0.0394(6) Uani 1 1 d . . . . .
H10A H 0.885738 0.303616 0.573793 0.059 Uiso 1 1 calc R U . . .
H10B H 0.969311 0.420677 0.571512 0.059 Uiso 1 1 calc R U . . .
H10C H 0.956397 0.344949 0.491225 0.059 Uiso 1 1 calc R U . . .
C11 C 0.6837(2) 0.35497(18) 0.46921(15) 0.0290(5) Uani 1 1 d . . . . .
H11A H 0.656655 0.290267 0.503070 0.043 Uiso 1 1 calc R U . . .
H11B H 0.732454 0.327363 0.421067 0.043 Uiso 1 1 calc R U . . .
H11C H 0.601459 0.396899 0.452398 0.043 Uiso 1 1 calc R U . . .
C12 C 0.7067(2) 0.4782(2) 0.59344(13) 0.0327(5) Uani 1 1 d . . . . .
H12A H 0.684497 0.414694 0.629562 0.049 Uiso 1 1 calc R U . . .
H12B H 0.622007 0.517738 0.578063 0.049 Uiso 1 1 calc R U . . .
H12C H 0.768179 0.531204 0.621528 0.049 Uiso 1 1 calc R U . . .
C21 C 0.8775(2) 0.68028(17) 0.30708(12) 0.0237(4) Uani 1 1 d . . . . .
H21 H 0.811176 0.645401 0.268010 0.028 Uiso 1 1 calc R U . . .
C22 C 1.0026(2) 0.6012(2) 0.31673(13) 0.0299(5) Uani 1 1 d . . . . .
H22A H 1.052741 0.617814 0.367653 0.036 Uiso 1 1 calc R U . . .
H22B H 0.973975 0.520510 0.316962 0.036 Uiso 1 1 calc R U . . .
C23 C 1.0916(2) 0.6275(2) 0.24284(14) 0.0397(6) Uani 1 1 d . . . . .
H23A H 1.189625 0.612057 0.254460 0.048 Uiso 1 1 calc R U . . .
H23B H 1.062800 0.581178 0.195661 0.048 Uiso 1 1 calc R U . . .
C24 C 1.0688(3) 0.7515(3) 0.2267(3) 0.0704(11) Uani 1 1 d . . . . .
H24A H 1.147902 0.796009 0.247143 0.084 Uiso 1 1 calc R U . . .
H24B H 1.060478 0.764791 0.167624 0.084 Uiso 1 1 calc R U . . .
C25 C 0.9411(3) 0.7880(2) 0.26837(17) 0.0449(7) Uani 1 1 d . . . . .
H25A H 0.876273 0.822156 0.228999 0.054 Uiso 1 1 calc R U . . .
H25B H 0.962253 0.845060 0.310696 0.054 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
C5 O2 C6 115.71(17) . . ?
C7 O4 C8 115.55(15) . . ?
C1 N1 C4 109.02(16) . . ?
C1 N2 C9 126.78(16) . . ?
N2 C1 N1 122.78(17) . . ?
N2 C1 C2 121.50(16) . . ?
N1 C1 C2 115.69(16) . . ?
C1 C2 C21 115.37(15) . . ?
C1 C2 C3 99.60(13) . . ?
C21 C2 C3 116.78(15) . . ?
C5 C3 C7 110.25(15) . . ?
C5 C3 C4 105.11(15) . . ?
C7 C3 C4 110.37(14) . . ?
C5 C3 C2 118.94(15) . . ?
C7 C3 C2 108.78(14) . . ?
C4 C3 C2 102.93(14) . . ?
N1 C4 C3 111.31(15) . . ?
N1 C4 S 125.42(14) . . ?
C3 C4 S 123.27(14) . . ?
O1 C5 O2 124.72(18) . . ?
O1 C5 C3 124.53(18) . . ?
O2 C5 C3 110.58(15) . . ?
O3 C7 O4 124.34(18) . . ?
O3 C7 C3 125.06(17) . . ?
O4 C7 C3 110.59(15) . . ?
N2 C9 C11 109.69(17) . . ?
N2 C9 C12 109.53(17) . . ?
C11 C9 C12 111.62(17) . . ?
N2 C9 C10 105.98(16) . . ?
C11 C9 C10 109.75(18) . . ?
C12 C9 C10 110.12(19) . . ?
C22 C21 C2 114.90(16) . . ?
C22 C21 C25 102.81(18) . . ?
C2 C21 C25 111.33(17) . . ?
C23 C22 C21 104.08(18) . . ?
C24 C23 C22 104.8(2) . . ?
C25 C24 C23 108.9(2) . . ?
C24 C25 C21 106.7(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 1.6454(18) . ?
O1 C5 1.201(2) . ?
O2 C5 1.333(2) . ?
O2 C6 1.452(3) . ?
O3 C7 1.202(2) . ?
O4 C7 1.327(2) . ?
O4 C8 1.446(2) . ?
N1 C1 1.335(2) . ?
N1 C4 1.349(2) . ?
N2 C1 1.310(3) . ?
N2 C9 1.493(2) . ?
C1 C2 1.525(2) . ?
C2 C21 1.546(3) . ?
C2 C3 1.563(2) . ?
C3 C5 1.531(2) . ?
C3 C7 1.532(2) . ?
C3 C4 1.558(3) . ?
C9 C11 1.522(3) . ?
C9 C12 1.524(3) . ?
C9 C10 1.528(3) . ?
C21 C22 1.541(3) . ?
C21 C25 1.548(3) . ?
C22 C23 1.526(3) . ?
C23 C24 1.500(4) . ?
C24 C25 1.483(4) . ?
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 -4.0(3) . . . . ?
C9 N2 C1 C2 174.24(17) . . . . ?
C4 N1 C1 N2 172.26(17) . . . . ?
C4 N1 C1 C2 -6.1(2) . . . . ?
N2 C1 C2 C21 67.1(2) . . . . ?
N1 C1 C2 C21 -114.51(18) . . . . ?
N2 C1 C2 C3 -167.04(16) . . . . ?
N1 C1 C2 C3 11.4(2) . . . . ?
C1 C2 C3 C5 -126.64(17) . . . . ?
C21 C2 C3 C5 -1.7(2) . . . . ?
C1 C2 C3 C7 106.08(16) . . . . ?
C21 C2 C3 C7 -129.02(16) . . . . ?
C1 C2 C3 C4 -11.01(16) . . . . ?
C21 C2 C3 C4 113.89(17) . . . . ?
C1 N1 C4 C3 -2.4(2) . . . . ?
C1 N1 C4 S 176.97(14) . . . . ?
C5 C3 C4 N1 134.39(16) . . . . ?
C7 C3 C4 N1 -106.75(17) . . . . ?
C2 C3 C4 N1 9.21(19) . . . . ?
C5 C3 C4 S -45.0(2) . . . . ?
C7 C3 C4 S 73.88(19) . . . . ?
C2 C3 C4 S -170.17(13) . . . . ?
C6 O2 C5 O1 5.8(3) . . . . ?
C6 O2 C5 C3 -169.61(19) . . . . ?
C7 C3 C5 O1 173.62(19) . . . . ?
C4 C3 C5 O1 -67.4(2) . . . . ?
C2 C3 C5 O1 47.0(3) . . . . ?
C7 C3 C5 O2 -11.0(2) . . . . ?
C4 C3 C5 O2 107.97(17) . . . . ?
C2 C3 C5 O2 -137.57(17) . . . . ?
C8 O4 C7 O3 -0.1(3) . . . . ?
C8 O4 C7 C3 -179.23(15) . . . . ?
C5 C3 C7 O3 107.2(2) . . . . ?
C4 C3 C7 O3 -8.5(2) . . . . ?
C2 C3 C7 O3 -120.70(19) . . . . ?
C5 C3 C7 O4 -73.64(19) . . . . ?
C4 C3 C7 O4 170.68(14) . . . . ?
C2 C3 C7 O4 58.44(18) . . . . ?
C1 N2 C9 C11 61.6(3) . . . . ?
C1 N2 C9 C12 -61.2(3) . . . . ?
C1 N2 C9 C10 -180.0(2) . . . . ?
C1 C2 C21 C22 -60.3(2) . . . . ?
C3 C2 C21 C22 -176.83(17) . . . . ?
C1 C2 C21 C25 -176.67(18) . . . . ?
C3 C2 C21 C25 66.8(2) . . . . ?
C2 C21 C22 C23 -156.04(19) . . . . ?
C25 C21 C22 C23 -34.9(2) . . . . ?
C21 C22 C23 C24 33.2(3) . . . . ?
C22 C23 C24 C25 -18.4(4) . . . . ?
C23 C24 C25 C21 -3.8(4) . . . . ?
C22 C21 C25 C24 24.0(3) . . . . ?
C2 C21 C25 C24 147.5(3) . . . . ?
