#------------------------------------------------------------------------------
#$Date: 2021-01-22 00:22:14 +0200 (Fri, 22 Jan 2021) $
#$Revision: 261115 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/84/4518411.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_4518411
loop_
_publ_author_name
'Zhu, Bo-Han'
'Zhang, Ying-Qi'
'Xu, Hao-Jin'
'Li, Long'
'Deng, Guo-Cheng'
'Qian, Peng-Cheng'
'Deng, Chao'
'Ye, Long-Wu'
_publ_section_title
;
 Regio- and Stereoselective Synthesis of Diverse 3,4-Dihydro-2-quinolones
 through Catalytic Hydrative Cyclization of Imine- and Carbonyl-Ynamides
 with Water
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              1706
_journal_page_last               1713
_journal_paper_doi               10.1021/acscatal.0c04786
_journal_year                    2021
_chemical_formula_moiety         'C27 H30 N2 O5 S2'
_chemical_formula_sum            'C27 H30 N2 O5 S2'
_chemical_formula_weight         526.65
_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             2021-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                91.099(5)
_cell_angle_beta                 93.667(5)
_cell_angle_gamma                105.210(5)
_cell_formula_units_Z            2
_cell_length_a                   9.172(3)
_cell_length_b                   11.675(3)
_cell_length_c                   12.090(4)
_cell_measurement_reflns_used    2425
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.34
_cell_measurement_theta_min      2.31
_cell_volume                     1245.9(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.955
_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  0.0528
_diffrn_reflns_av_unetI/netI     0.0992
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9780
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.500
_diffrn_reflns_theta_min         1.689
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0656
_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)+(0.0931P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1650
_refine_ls_wR_factor_ref         0.1801
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2991
_reflns_number_total             4945
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c04786_si_002.cif
_cod_data_source_block           y0925m
_cod_original_cell_volume        1245.9(6)
_cod_database_code               4518411
_shelxl_version_number           2014-3
_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_max   0.982
_shelx_estimated_absorpt_t_min   0.943
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C22(H22), C21(H21), C19(H19), C18(H18)
2.c Fitted hexagon refined as free rotating group:
 C9(C4,C5,C6,C7,C8), C10(C11,C12,C13,C14,C15), C17(C22,C21,C20,C19,C18)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C)
;
_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 0.02944(10) 0.64492(8) 0.79176(7) 0.0346(3) Uani 1 1 d . . . . .
S2 S 0.15066(11) 0.83802(7) 0.27557(7) 0.0340(3) Uani 1 1 d . . . . .
O1 O 0.1220(3) 0.5163(2) 0.6159(2) 0.0433(7) Uani 1 1 d . . . . .
O2 O 0.0056(3) 0.7456(2) 0.8463(2) 0.0429(6) Uani 1 1 d . . . . .
O3 O -0.0940(3) 0.5612(2) 0.7370(2) 0.0435(7) Uani 1 1 d . . . . .
O4 O 0.0064(3) 0.7646(2) 0.2939(2) 0.0477(7) Uani 1 1 d . . . . .
O5 O 0.2367(3) 0.8046(2) 0.1933(2) 0.0490(7) Uani 1 1 d . . . . .
N1 N 0.1490(3) 0.6998(2) 0.6922(2) 0.0313(7) Uani 1 1 d . . . . .
N2 N 0.2531(3) 0.8544(2) 0.3907(2) 0.0312(7) Uani 1 1 d . . . . .
H2 H 0.3451 0.8973 0.3931 0.037 Uiso 1 1 calc R . . . .
C1 C 0.1608(4) 0.6206(3) 0.6062(3) 0.0310(8) Uani 1 1 d . . . . .
C2 C 0.2195(4) 0.6754(3) 0.5012(3) 0.0288(8) Uani 1 1 d . . . . .
H2A H 0.1572 0.6260 0.4401 0.035 Uiso 1 1 calc R . . . .
C3 C 0.1946(4) 0.7988(3) 0.4903(3) 0.0284(8) Uani 1 1 d . . . . .
H3 H 0.0849 0.7890 0.4845 0.034 Uiso 1 1 calc R . . . .
C9 C 0.2326(2) 0.82018(12) 0.69373(16) 0.0282(7) Uani 1 1 d . . . . .
C4 C 0.2572(2) 0.87368(15) 0.59242(13) 0.0262(7) Uani 1 1 d G . . . .
C5 C 0.3311(2) 0.99375(16) 0.58942(13) 0.0298(8) Uani 1 1 d G . . . .
H5 H 0.3475 1.0296 0.5216 0.036 Uiso 1 1 calc R . . . .
C6 C 0.3803(2) 1.06031(12) 0.68772(17) 0.0330(8) Uani 1 1 d G . . . .
H6 H 0.4297 1.1406 0.6857 0.040 Uiso 1 1 calc R . . . .
C7 C 0.3557(2) 1.00681(16) 0.78902(14) 0.0327(8) Uani 1 1 d G . . . .
C8 C 0.2818(2) 0.88674(17) 0.79203(13) 0.0341(8) Uani 1 1 d G . . . .
H8 H 0.2654 0.8509 0.8598 0.041 Uiso 1 1 calc R . . . .
C10 C 0.3777(2) 0.6687(2) 0.48920(18) 0.0311(8) Uani 1 1 d . . . . .
C11 C 0.4878(3) 0.6997(2) 0.57692(16) 0.0416(9) Uani 1 1 d G . . . .
H11 H 0.4634 0.7256 0.6448 0.050 Uiso 1 1 calc R . . . .
C12 C 0.6343(2) 0.6921(2) 0.5631(2) 0.0509(11) Uani 1 1 d G . . . .
H12 H 0.7079 0.7129 0.6218 0.061 Uiso 1 1 calc R . . . .
C13 C 0.6707(2) 0.6535(2) 0.4616(2) 0.0543(11) Uani 1 1 d G . . . .
H13 H 0.7687 0.6484 0.4524 0.065 Uiso 1 1 calc R . . . .
C14 C 0.5606(3) 0.6224(2) 0.37388(19) 0.0528(11) Uani 1 1 d G . . . .
H14 H 0.5850 0.5966 0.3060 0.063 Uiso 1 1 calc R . . . .
C15 C 0.4141(3) 0.6300(2) 0.38767(16) 0.0405(9) Uani 1 1 d G . . . .
H15 H 0.3404 0.6093 0.3290 0.049 Uiso 1 1 calc R . . . .
C16 C 0.4033(4) 1.0798(3) 0.8942(3) 0.0477(10) Uani 1 1 d . . . . .
H16A H 0.3669 1.0325 0.9558 0.072 Uiso 1 1 calc GR . . . .
H16B H 0.3619 1.1472 0.8920 0.072 Uiso 1 1 calc GR . . . .
H16C H 0.5119 1.1065 0.9025 0.072 Uiso 1 1 calc GR . . . .
C17 C 0.1264(2) 0.57526(17) 0.88158(16) 0.0310(8) Uani 1 1 d . . . . .
C22 C 0.1351(3) 0.46081(17) 0.85581(15) 0.0417(10) Uani 1 1 d G . . . .
H22 H 0.0884 0.4223 0.7898 0.050 Uiso 1 1 calc R . . . .
C21 C 0.2138(3) 0.40388(14) 0.92876(19) 0.0446(10) Uani 1 1 d G . . . .
H21 H 0.2196 0.3273 0.9115 0.054 Uiso 1 1 calc R . . . .
C20 C 0.2837(2) 0.46141(19) 1.02748(17) 0.0394(9) Uani 1 1 d G . . . .
C19 C 0.2750(3) 0.57586(18) 1.05324(14) 0.0408(9) Uani 1 1 d G . . . .
H19 H 0.3218 0.6143 1.1193 0.049 Uiso 1 1 calc R . . . .
C18 C 0.1964(3) 0.63278(14) 0.98029(17) 0.0394(9) Uani 1 1 d G . . . .
H18 H 0.1905 0.7094 0.9975 0.047 Uiso 1 1 calc R . . . .
C23 C 0.3677(5) 0.4001(4) 1.1048(3) 0.0527(11) Uani 1 1 d . . . . .
H23A H 0.4745 0.4360 1.1036 0.079 Uiso 1 1 calc GR . . . .
H23B H 0.3459 0.3177 1.0822 0.079 Uiso 1 1 calc GR . . . .
H23C H 0.3371 0.4069 1.1786 0.079 Uiso 1 1 calc GR . . . .
C24 C 0.1296(4) 0.9818(3) 0.2451(3) 0.0322(8) Uani 1 1 d . . . . .
C25 C 0.2826(4) 1.0634(3) 0.2309(3) 0.0461(10) Uani 1 1 d . . . . .
H25A H 0.3446 1.0704 0.2990 0.069 Uiso 1 1 calc GR . . . .
H25B H 0.2718 1.1403 0.2115 0.069 Uiso 1 1 calc GR . . . .
H25C H 0.3294 1.0319 0.1729 0.069 Uiso 1 1 calc GR . . . .
C26 C 0.0315(5) 0.9652(4) 0.1371(3) 0.0580(12) Uani 1 1 d . . . . .
H26A H 0.0765 0.9281 0.0819 0.087 Uiso 1 1 calc GR . . . .
H26B H 0.0235 1.0412 0.1126 0.087 Uiso 1 1 calc GR . . . .
H26C H -0.0676 0.9159 0.1486 0.087 Uiso 1 1 calc GR . . . .
C27 C 0.0548(4) 1.0255(3) 0.3384(3) 0.0428(9) Uani 1 1 d . . . . .
H27A H -0.0393 0.9686 0.3495 0.064 Uiso 1 1 calc GR . . . .
H27B H 0.0358 1.1001 0.3201 0.064 Uiso 1 1 calc GR . . . .
H27C H 0.1202 1.0356 0.4051 0.064 Uiso 1 1 calc GR . . . .
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
O2 S1 N1 105.12(14) . . ?
O2 S1 C17 109.16(13) . . ?
O3 S1 O2 119.63(16) . . ?
O3 S1 N1 105.89(14) . . ?
O3 S1 C17 109.94(13) . . ?
N1 S1 C17 106.15(14) . . ?
O4 S2 O5 119.98(16) . . ?
O4 S2 N2 107.84(15) . . ?
O4 S2 C24 107.81(17) . . ?
O5 S2 N2 106.76(16) . . ?
O5 S2 C24 107.82(17) . . ?
N2 S2 C24 105.82(14) . . ?
C1 N1 S1 117.3(2) . . ?
C1 N1 C9 120.6(2) . . ?
C9 N1 S1 122.1(2) . . ?
S2 N2 H2 119.1 . . ?
C3 N2 S2 121.8(2) . . ?
C3 N2 H2 119.1 . . ?
O1 C1 N1 121.3(3) . . ?
O1 C1 C2 122.4(3) . . ?
N1 C1 C2 116.3(3) . . ?
C1 C2 H2A 106.3 . . ?
C1 C2 C3 111.1(3) . . ?
C3 C2 H2A 106.3 . . ?
C10 C2 C1 111.2(2) . . ?
C10 C2 H2A 106.3 . . ?
C10 C2 C3 115.2(2) . . ?
N2 C3 C2 112.1(3) . . ?
N2 C3 H3 107.2 . . ?
N2 C3 C4 112.5(2) . . ?
C2 C3 H3 107.2 . . ?
C4 C3 C2 110.4(2) . . ?
C4 C3 H3 107.2 . . ?
C4 C9 N1 117.68(16) . . ?
C4 C9 C8 120.0 . . ?
C8 C9 N1 122.21(17) . . ?
C9 C4 C3 117.25(16) . . ?
C5 C4 C3 122.68(16) . . ?
C5 C4 C9 120.0 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C8 120.0 . . ?
C6 C7 C16 119.7(2) . . ?
C8 C7 C16 120.2(2) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 C9 120.0 . . ?
C7 C8 H8 120.0 . . ?
C11 C10 C2 121.42(19) . . ?
C11 C10 C15 120.0 . . ?
C15 C10 C2 118.58(19) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C10 C15 H15 120.0 . . ?
C14 C15 C10 120.0 . . ?
C14 C15 H15 120.0 . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 S1 119.87(13) . . ?
C22 C17 C18 120.0 . . ?
C18 C17 S1 120.13(13) . . ?
C17 C22 H22 120.0 . . ?
C17 C22 C21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C21 H21 120.0 . . ?
C20 C21 C22 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C20 C23 119.7(2) . . ?
C19 C20 C21 120.0 . . ?
C19 C20 C23 120.3(2) . . ?
C20 C19 H19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 S2 109.0(3) . . ?
C25 C24 C26 110.5(3) . . ?
C25 C24 C27 111.2(3) . . ?
C26 C24 S2 105.4(2) . . ?
C27 C24 S2 108.9(2) . . ?
C27 C24 C26 111.7(3) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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 O2 1.410(3) . ?
S1 O3 1.405(2) . ?
S1 N1 1.701(3) . ?
S1 C17 1.7095(18) . ?
S2 O4 1.409(3) . ?
S2 O5 1.418(3) . ?
S2 N2 1.608(3) . ?
S2 C24 1.782(3) . ?
O1 C1 1.186(4) . ?
N1 C1 1.407(4) . ?
N1 C9 1.412(3) . ?
N2 H2 0.8600 . ?
N2 C3 1.445(4) . ?
C1 C2 1.500(4) . ?
C2 H2A 0.9800 . ?
C2 C3 1.524(4) . ?
C2 C10 1.489(4) . ?
C3 H3 0.9800 . ?
C3 C4 1.491(3) . ?
C9 C4 1.3900 . ?
C9 C8 1.3900 . ?
C4 C5 1.3900 . ?
C5 H5 0.9300 . ?
C5 C6 1.3900 . ?
C6 H6 0.9300 . ?
C6 C7 1.3900 . ?
C7 C8 1.3900 . ?
C7 C16 1.492(4) . ?
C8 H8 0.9300 . ?
C10 C11 1.3900 . ?
C10 C15 1.3900 . ?
C11 H11 0.9300 . ?
C11 C12 1.3900 . ?
C12 H12 0.9300 . ?
C12 C13 1.3900 . ?
C13 H13 0.9300 . ?
C13 C14 1.3900 . ?
C14 H14 0.9300 . ?
C14 C15 1.3900 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C22 1.3900 . ?
C17 C18 1.3900 . ?
C22 H22 0.9300 . ?
C22 C21 1.3900 . ?
C21 H21 0.9300 . ?
C21 C20 1.3900 . ?
C20 C19 1.3900 . ?
C20 C23 1.485(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.3900 . ?
C18 H18 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.497(5) . ?
C24 C26 1.517(5) . ?
C24 C27 1.504(5) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
