#------------------------------------------------------------------------------
#$Date: 2020-06-05 12:41:26 +0300 (Fri, 05 Jun 2020) $
#$Revision: 252680 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/63/7126394.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_7126394
loop_
_publ_author_name
'Babu, Kaki Raveendra'
'Han, Wendan'
'Chen, Jian-Bo'
'Li, Yang'
'Tang, Yuhai'
'Zhang, Wenquan'
'Xu, Wenbo'
'Xu, Silong'
_publ_section_title
;
 A three-component reaction of phosphorus ylides with isocyanates: facile
 synthesis of 2-amino-3-carboxylate-4-quinolones.
;
_journal_issue                   44
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5909
_journal_page_last               5912
_journal_paper_doi               10.1039/d0cc01401j
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C13 H15 N O2 S'
_chemical_formula_weight         249.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-12-02 deposited with the CCDC.	2020-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.037(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.037(7)
_cell_length_b                   5.654(3)
_cell_length_c                   16.695(8)
_cell_measurement_reflns_used    4686
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      2.46
_cell_volume                     1275.3(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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  0.0233
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12841
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_min         1.507
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       lump
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.953
_exptl_transmission_factor_min   0.948
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0595P)²+0.4584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1124
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2123
_reflns_number_total             2630
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc01401j2.cif
_cod_data_source_block           mo_Hexin_20190505_1_0m
_cod_depositor_comments
'Adding full bibliography for 7126391--7126394.cif.'
_cod_original_cell_volume        1275.4(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7126394
_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_min   0.948
_shelx_estimated_absorpt_t_max   0.953
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.40398(3) 0.80956(9) 0.23341(3) 0.04819(17) Uani 1 1 d . . . . .
C1 C 0.35662(14) 1.0537(4) 0.15608(16) 0.0613(6) Uani 1 1 d . . . . .
H1A H 0.384354 1.201693 0.186045 0.074 Uiso 1 1 calc R U . . .
H1B H 0.374521 1.034135 0.107285 0.074 Uiso 1 1 calc R U . . .
N1 N 0.21908(10) 0.9107(3) 0.17529(11) 0.0470(4) Uani 1 1 d . . . . .
O1 O 0.31586(8) 0.3027(2) 0.39163(9) 0.0483(3) Uani 1 1 d . . . . .
C2 C 0.24970(15) 1.0559(5) 0.12244(17) 0.0765(8) Uani 1 1 d . . . . .
H2A H 0.227418 1.216796 0.122702 0.092 Uiso 1 1 calc R U . . .
H2B H 0.219464 0.999563 0.061372 0.092 Uiso 1 1 calc R U . . .
O2 O 0.43596(9) 0.4499(3) 0.35945(9) 0.0563(4) Uani 1 1 d . . . . .
C3 C 0.28915(11) 0.7622(3) 0.23403(11) 0.0390(4) Uani 1 1 d . . . . .
C4 C 0.27244(12) 0.6000(3) 0.28601(12) 0.0428(4) Uani 1 1 d . . . . .
H4 H 0.208957 0.584832 0.281825 0.051 Uiso 1 1 calc R U . . .
C5 C 0.35005(12) 0.4511(3) 0.34725(12) 0.0423(4) Uani 1 1 d . . . . .
C6 C 0.38782(14) 0.1388(4) 0.45240(13) 0.0525(5) Uani 1 1 d . . . . .
H6A H 0.439430 0.224319 0.500956 0.063 Uiso 1 1 calc R U . . .
H6B H 0.418119 0.048713 0.421443 0.063 Uiso 1 1 calc R U . . .
C7 C 0.33481(16) -0.0238(4) 0.48793(15) 0.0597(5) Uani 1 1 d . . . . .
H7A H 0.381053 -0.134618 0.528526 0.090 Uiso 1 1 calc R U . . .
H7B H 0.305324 0.066951 0.518605 0.090 Uiso 1 1 calc R U . . .
H7C H 0.284099 -0.107952 0.439410 0.090 Uiso 1 1 calc R U . . .
C8 C 0.11665(11) 0.8958(3) 0.15681(11) 0.0390(4) Uani 1 1 d . . . . .
C9 C 0.07501(14) 1.0741(4) 0.18517(15) 0.0540(5) Uani 1 1 d . . . . .
H9 H 0.113576 1.200528 0.217609 0.065 Uiso 1 1 calc R U . . .
C10 C -0.02521(14) 1.0645(4) 0.16511(16) 0.0583(5) Uani 1 1 d . . . . .
H10 H -0.053641 1.185776 0.183665 0.070 Uiso 1 1 calc R U . . .
C11 C -0.08217(13) 0.8768(4) 0.11805(12) 0.0506(5) Uani 1 1 d . . . . .
H11 H -0.149099 0.871173 0.104438 0.061 Uiso 1 1 calc R U . . .
C12 C -0.03996(14) 0.6980(4) 0.09128(13) 0.0560(5) Uani 1 1 d . . . . .
H12 H -0.078302 0.569771 0.060204 0.067 Uiso 1 1 calc R U . . .
C13 C 0.05956(13) 0.7063(4) 0.11006(13) 0.0511(5) Uani 1 1 d . . . . .
H13 H 0.087619 0.584823 0.091240 0.061 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
C3 S1 C1 92.33(8) . . ?
C2 C1 S1 107.74(14) . . ?
C2 C1 H1A 110.2 . . ?
S1 C1 H1A 110.2 . . ?
C2 C1 H1B 110.2 . . ?
S1 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
C3 N1 C2 116.25(15) . . ?
C3 N1 C8 122.35(14) . . ?
C2 N1 C8 120.66(15) . . ?
C5 O1 C6 115.57(14) . . ?
N1 C2 C1 111.12(17) . . ?
N1 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 N1 124.87(15) . . ?
C4 C3 S1 124.45(13) . . ?
N1 C3 S1 110.67(13) . . ?
C3 C4 C5 121.93(15) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
O2 C5 O1 122.19(16) . . ?
O2 C5 C4 126.38(17) . . ?
O1 C5 C4 111.43(14) . . ?
O1 C6 C7 107.84(16) . . ?
O1 C6 H6A 110.1 . . ?
C7 C6 H6A 110.1 . . ?
O1 C6 H6B 110.1 . . ?
C7 C6 H6B 110.1 . . ?
H6A C6 H6B 108.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 119.95(16) . . ?
C9 C8 N1 119.42(17) . . ?
C13 C8 N1 120.62(16) . . ?
C8 C9 C10 119.76(19) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 120.28(18) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 119.70(17) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.64(19) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C12 119.66(18) . . ?
C8 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
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
S1 C3 1.7519(18) . ?
S1 C1 1.809(2) . ?
C1 C2 1.452(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
N1 C3 1.367(2) . ?
N1 C2 1.422(3) . ?
N1 C8 1.434(2) . ?
O1 C5 1.361(2) . ?
O1 C6 1.448(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
O2 C5 1.216(2) . ?
C3 C4 1.360(3) . ?
C4 C5 1.438(2) . ?
C4 H4 0.9300 . ?
C6 C7 1.499(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.376(3) . ?
C8 C13 1.381(3) . ?
C9 C10 1.394(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
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
C3 S1 C1 C2 -10.5(2) . . . . ?
C3 N1 C2 C1 -12.8(3) . . . . ?
C8 N1 C2 C1 176.9(2) . . . . ?
S1 C1 C2 N1 14.5(3) . . . . ?
C2 N1 C3 C4 -175.7(2) . . . . ?
C8 N1 C3 C4 -5.5(3) . . . . ?
C2 N1 C3 S1 4.4(2) . . . . ?
C8 N1 C3 S1 174.58(14) . . . . ?
C1 S1 C3 C4 -176.14(18) . . . . ?
C1 S1 C3 N1 3.79(15) . . . . ?
N1 C3 C4 C5 -179.24(17) . . . . ?
S1 C3 C4 C5 0.7(3) . . . . ?
C6 O1 C5 O2 -1.7(3) . . . . ?
C6 O1 C5 C4 177.62(16) . . . . ?
C3 C4 C5 O2 -0.5(3) . . . . ?
C3 C4 C5 O1 -179.79(17) . . . . ?
C5 O1 C6 C7 -174.62(16) . . . . ?
C3 N1 C8 C9 111.0(2) . . . . ?
C2 N1 C8 C9 -79.2(3) . . . . ?
C3 N1 C8 C13 -69.8(2) . . . . ?
C2 N1 C8 C13 100.0(3) . . . . ?
C13 C8 C9 C10 -1.2(3) . . . . ?
N1 C8 C9 C10 178.05(18) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C13 -1.0(3) . . . . ?
C9 C8 C13 C12 0.6(3) . . . . ?
N1 C8 C13 C12 -178.64(17) . . . . ?
C11 C12 C13 C8 0.5(3) . . . . ?
