#------------------------------------------------------------------------------
#$Date: 2025-03-07 18:30:27 +0200 (Fri, 07 Mar 2025) $
#$Revision: 298328 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/85/7158519.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_7158519
loop_
_publ_author_name
'Yao, Wen-Bo'
'Xie, Xuan-Sheng'
'Liu, Jun-Nan'
'Xie, Jian-Wu'
_publ_section_title
;
 Diversity-oriented and diastereoselective synthesis of diverse polycyclic
 thieno(2,3-b)-quinoline derivatives using a synergistic strategy.
;
_journal_issue                   9
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1982
_journal_page_last               1993
_journal_paper_doi               10.1039/d2ob00020b
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C16 H15 N O2 S'
_chemical_formula_sum            'C16 H15 N O2 S'
_chemical_formula_weight         285.36
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2020-07-02 deposited with the CCDC.	2022-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.411(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5115(13)
_cell_length_b                   10.484(2)
_cell_length_c                   20.277(4)
_cell_measurement_reflns_used    7632
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.34
_cell_measurement_theta_min      2.80
_cell_volume                     1380.1(5)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            44448
_diffrn_reflns_theta_full        27.28
_diffrn_reflns_theta_max         27.28
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          .32
_exptl_crystal_size_mid          .21
_exptl_crystal_size_min          .16
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0206(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3095
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0431P)²+0.4978P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1113
_reflns_number_gt                2544
_reflns_number_total             3095
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ob00020b2.cif
_cod_data_source_block           5ca
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7158516--7158520.cif.

2025-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C3.56 H3.33 N0.22 O0.44 S0.22'
_cod_original_formula_weight         63.41
_cod_original_formula_moiety         'C3.56 H3.33 N0.22 O0.44 S0.22'
_cod_original_formula_units_Z            18
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7158519
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.83189(8) 0.60095(4) 0.05322(3) 0.04557(17) Uani 1 1 d . . .
N1 N 1.1776(2) 0.60488(14) 0.13549(8) 0.0425(4) Uani 1 1 d . . .
O2 O 0.73842(19) 0.97166(12) 0.08530(6) 0.0424(3) Uani 1 1 d . . .
H2A H 0.8246 0.9991 0.0615 0.064 Uiso 1 1 calc R . .
O1 O 1.01561(19) 0.87142(12) -0.00903(7) 0.0430(3) Uani 1 1 d . . .
C2 C 0.7645(3) 0.83925(17) 0.09347(9) 0.0360(4) Uani 1 1 d . . .
H2B H 0.6591 0.8115 0.1224 0.043 Uiso 1 1 calc R . .
C3 C 0.9681(3) 0.79721(17) 0.12650(8) 0.0349(4) Uani 1 1 d . . .
C16 C 0.8686(2) 0.80306(16) -0.02365(9) 0.0342(4) Uani 1 1 d . . .
C1 C 0.7293(2) 0.76064(16) 0.02932(9) 0.0343(4) Uani 1 1 d . . .
C4 C 1.1017(3) 0.86272(18) 0.16834(9) 0.0402(4) Uani 1 1 d . . .
H4A H 1.0756 0.9472 0.1790 0.048 Uiso 1 1 calc R . .
C5 C 1.2827(3) 0.80011(19) 0.19568(9) 0.0419(4) Uani 1 1 d . . .
C11 C 1.0164(3) 0.66898(17) 0.11141(9) 0.0362(4) Uani 1 1 d . . .
C12 C 0.5022(3) 0.7560(2) 0.00330(10) 0.0472(5) Uani 1 1 d . . .
H12A H 0.4262 0.7074 0.0340 0.057 Uiso 1 1 calc R . .
H12B H 0.4476 0.8421 0.0020 0.057 Uiso 1 1 calc R . .
C9 C 1.4913(3) 0.6074(2) 0.20580(11) 0.0543(5) Uani 1 1 d . . .
H9A H 1.5135 0.5227 0.1948 0.065 Uiso 1 1 calc R . .
C10 C 1.3124(3) 0.67081(19) 0.17879(9) 0.0412(4) Uani 1 1 d . . .
C15 C 0.8198(3) 0.7553(2) -0.09283(10) 0.0493(5) Uani 1 1 d . . .
H15A H 0.8627 0.6670 -0.0955 0.059 Uiso 1 1 calc R . .
H15B H 0.8972 0.8046 -0.1230 0.059 Uiso 1 1 calc R . .
C14 C 0.5910(3) 0.7652(2) -0.11425(11) 0.0593(6) Uani 1 1 d . . .
H14A H 0.5508 0.8542 -0.1170 0.071 Uiso 1 1 calc R . .
H14B H 0.5641 0.7273 -0.1577 0.071 Uiso 1 1 calc R . .
C6 C 1.4319(3) 0.8612(2) 0.23909(10) 0.0530(5) Uani 1 1 d . . .
H6A H 1.4136 0.9461 0.2507 0.064 Uiso 1 1 calc R . .
C7 C 1.6026(3) 0.7968(3) 0.26416(11) 0.0613(6) Uani 1 1 d . . .
H7A H 1.7004 0.8383 0.2923 0.074 Uiso 1 1 calc R . .
C8 C 1.6314(3) 0.6693(3) 0.24780(11) 0.0613(6) Uani 1 1 d . . .
H8A H 1.7473 0.6259 0.2657 0.074 Uiso 1 1 calc R . .
C13 C 0.4659(3) 0.6971(2) -0.06514(12) 0.0595(6) Uani 1 1 d . . .
H13A H 0.5042 0.6077 -0.0632 0.071 Uiso 1 1 calc R . .
H13B H 0.3207 0.7025 -0.0797 0.071 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
C11 S1 C1 91.31(8) . . ?
C11 N1 C10 115.68(16) . . ?
O2 C2 C3 115.82(15) . . ?
O2 C2 C1 114.79(14) . . ?
C3 C2 C1 106.71(14) . . ?
C4 C3 C11 118.24(16) . . ?
C4 C3 C2 129.18(17) . . ?
C11 C3 C2 112.56(15) . . ?
O1 C16 C15 122.11(16) . . ?
O1 C16 C1 120.05(16) . . ?
C15 C16 C1 117.82(15) . . ?
C16 C1 C12 112.18(15) . . ?
C16 C1 C2 112.37(14) . . ?
C12 C1 C2 112.60(14) . . ?
C16 C1 S1 103.04(11) . . ?
C12 C1 S1 112.35(13) . . ?
C2 C1 S1 103.59(12) . . ?
C3 C4 C5 118.86(17) . . ?
C6 C5 C10 118.99(18) . . ?
C6 C5 C4 122.84(19) . . ?
C10 C5 C4 118.17(17) . . ?
N1 C11 C3 126.20(17) . . ?
N1 C11 S1 121.74(14) . . ?
C3 C11 S1 112.05(13) . . ?
C13 C12 C1 113.92(16) . . ?
C8 C9 C10 120.7(2) . . ?
N1 C10 C9 118.45(19) . . ?
N1 C10 C5 122.81(16) . . ?
C9 C10 C5 118.71(19) . . ?
C16 C15 C14 112.11(16) . . ?
C13 C14 C15 110.17(19) . . ?
C7 C6 C5 120.6(2) . . ?
C6 C7 C8 120.4(2) . . ?
C9 C8 C7 120.6(2) . . ?
C14 C13 C12 110.80(18) . . ?
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 C11 1.7683(19) . ?
S1 C1 1.8532(18) . ?
N1 C11 1.308(2) . ?
N1 C10 1.379(3) . ?
O2 C2 1.407(2) . ?
O1 C16 1.214(2) . ?
C2 C3 1.505(2) . ?
C2 C1 1.542(3) . ?
C3 C4 1.354(3) . ?
C3 C11 1.419(2) . ?
C16 C15 1.500(3) . ?
C16 C1 1.525(2) . ?
C1 C12 1.532(2) . ?
C4 C5 1.423(3) . ?
C5 C6 1.414(3) . ?
C5 C10 1.415(3) . ?
C12 C13 1.521(3) . ?
C9 C8 1.363(3) . ?
C9 C10 1.414(3) . ?
C15 C14 1.523(3) . ?
C14 C13 1.513(3) . ?
C6 C7 1.366(3) . ?
C7 C8 1.393(4) . ?
