#------------------------------------------------------------------------------
#$Date: 2020-04-05 14:11:35 +0300 (Sun, 05 Apr 2020) $
#$Revision: 250363 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/73/7157389.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_7157389
loop_
_publ_author_name
'Teng, Qiaoqiao'
'Singh, Chandan'
'Han, Yuan'
'Huynh, Han Vinh'
_publ_section_title
;
 Fused azole-thiazolines via one-pot cyclization of functionalized
 N-heterocyclic carbene precursors.
;
_journal_issue                   13
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2487
_journal_page_last               2491
_journal_paper_doi               10.1039/c9ob02548k
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C21 H21 N3 S2'
_chemical_formula_weight         379.53
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-03-26 deposited with the CCDC.	2020-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.2050(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1553(5)
_cell_length_b                   16.6915(10)
_cell_length_c                   14.5815(9)
_cell_measurement_reflns_used    1863
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      22.05
_cell_measurement_theta_min      2.56
_cell_volume                     1940.0(2)
_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      223(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0583
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13597
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.9667
_exptl_absorpt_correction_T_min  0.9560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4462
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0591
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0695P)²+0.0766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1459
_reflns_number_gt                3004
_reflns_number_total             4462
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob02548k2.cif
_cod_data_source_block           9558
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' 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.

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.

data item '_exptl_crystal_density_meas' value 'Not Measured' was
changed to '?' -- the value is perceived as not measured.

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

 Adding full bibliography for 7157386--7157390.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7157389
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.05589(8) 0.66300(3) 0.84113(4) 0.03672(19) Uani 1 1 d . . .
N1 N 0.9844(3) 0.52678(11) 0.74449(13) 0.0356(5) Uani 1 1 d . . .
N2 N 0.8161(3) 0.62095(11) 0.67936(13) 0.0349(5) Uani 1 1 d . . .
C1 C 0.9458(3) 0.60497(13) 0.74974(16) 0.0320(5) Uani 1 1 d . . .
C2 C 0.8763(3) 0.49330(15) 0.66789(17) 0.0449(7) Uani 1 1 d . . .
H2 H 0.8754 0.4396 0.6482 0.054 Uiso 1 1 calc R . .
C3 C 0.7735(4) 0.55161(14) 0.62715(18) 0.0458(7) Uani 1 1 d . . .
H3 H 0.6880 0.5465 0.5730 0.055 Uiso 1 1 calc R . .
C4 C 1.1072(3) 0.48378(12) 0.81348(16) 0.0311(5) Uani 1 1 d . . .
C5 C 1.0498(3) 0.43929(13) 0.88059(16) 0.0325(5) Uani 1 1 d . . .
C6 C 1.1688(3) 0.39713(13) 0.94527(16) 0.0357(6) Uani 1 1 d . . .
H6 H 1.1331 0.3657 0.9909 0.043 Uiso 1 1 calc R . .
C7 C 1.3385(3) 0.40006(13) 0.94445(17) 0.0370(6) Uani 1 1 d . . .
C8 C 1.3882(3) 0.44548(13) 0.87594(18) 0.0392(6) Uani 1 1 d . . .
H8 H 1.5030 0.4478 0.8749 0.047 Uiso 1 1 calc R . .
C9 C 1.2758(3) 0.48795(13) 0.80849(17) 0.0354(5) Uani 1 1 d . . .
C10 C 0.8671(3) 0.43714(16) 0.8859(2) 0.0489(7) Uani 1 1 d . . .
H10A H 0.8259 0.4914 0.8885 0.073 Uiso 1 1 calc R . .
H10B H 0.8548 0.4083 0.9418 0.073 Uiso 1 1 calc R . .
H10C H 0.8030 0.4103 0.8308 0.073 Uiso 1 1 calc R . .
C11 C 1.4660(4) 0.35496(16) 1.0160(2) 0.0565(8) Uani 1 1 d . . .
H11A H 1.5126 0.3116 0.9854 0.085 Uiso 1 1 calc R . .
H11B H 1.4121 0.3332 1.0639 0.085 Uiso 1 1 calc R . .
H11C H 1.5552 0.3911 1.0449 0.085 Uiso 1 1 calc R . .
C12 C 1.3347(4) 0.53579(16) 0.7346(2) 0.0551(8) Uani 1 1 d . . .
H12A H 1.3291 0.5924 0.7484 0.083 Uiso 1 1 calc R . .
H12B H 1.2636 0.5245 0.6737 0.083 Uiso 1 1 calc R . .
H12C H 1.4496 0.5213 0.7338 0.083 Uiso 1 1 calc R . .
C13 C 0.7336(3) 0.69896(14) 0.65040(17) 0.0386(6) Uani 1 1 d . . .
H13A H 0.6313 0.6890 0.6028 0.046 Uiso 1 1 calc R . .
H13B H 0.8087 0.7313 0.6211 0.046 Uiso 1 1 calc R . .
C14 C 0.6883(3) 0.74620(13) 0.72837(16) 0.0340(5) Uani 1 1 d . . .
C15 C 0.5207(3) 0.76038(15) 0.72994(18) 0.0429(6) Uani 1 1 d . . .
H15 H 0.4359 0.7369 0.6840 0.051 Uiso 1 1 calc R . .
C16 C 0.4776(4) 0.80834(17) 0.7979(2) 0.0531(7) Uani 1 1 d . . .
H16 H 0.3639 0.8172 0.7983 0.064 Uiso 1 1 calc R . .
C17 C 0.6001(4) 0.84335(17) 0.8652(2) 0.0512(7) Uani 1 1 d . . .
H17 H 0.5699 0.8768 0.9107 0.061 Uiso 1 1 calc R . .
C18 C 0.7679(3) 0.82952(14) 0.86618(18) 0.0419(6) Uani 1 1 d . . .
H18 H 0.8513 0.8529 0.9129 0.050 Uiso 1 1 calc R . .
C19 C 0.8132(3) 0.78091(12) 0.79790(16) 0.0321(5) Uani 1 1 d . . .
C20 C 0.9938(3) 0.76416(12) 0.79946(16) 0.0329(5) Uani 1 1 d . . .
H20A H 1.0635 0.8032 0.8404 0.040 Uiso 1 1 calc R . .
H20B H 1.0142 0.7708 0.7360 0.040 Uiso 1 1 calc R . .
S2A S 0.8744(3) 0.28502(16) 0.4448(2) 0.0617(8) Uani 0.656(7) 1 d PD A 1
N3A N 0.6420(10) 0.3980(4) 0.4831(5) 0.0680(17) Uani 0.656(7) 1 d PD A 1
C1A C 0.7414(9) 0.3530(4) 0.4680(5) 0.0470(18) Uani 0.656(7) 1 d PD A 1
C1B C 0.8288(17) 0.3171(8) 0.4423(9) 0.040(3) Uani 0.344(7) 1 d PD A 2
N3B N 0.9100(14) 0.2878(7) 0.3989(10) 0.081(4) Uani 0.344(7) 1 d PD A 2
S2B S 0.6964(6) 0.3613(3) 0.5008(3) 0.0581(14) Uani 0.344(7) 1 d PD A 2
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'
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
C1 S1 C20 101.43(11) . . ?
C1 N1 C2 108.65(19) . . ?
C1 N1 C4 125.08(19) . . ?
C2 N1 C4 125.98(18) . . ?
C1 N2 C3 108.69(19) . . ?
C1 N2 C13 129.13(19) . . ?
C3 N2 C13 121.94(19) . . ?
N2 C1 N1 107.82(19) . . ?
N2 C1 S1 132.48(17) . . ?
N1 C1 S1 119.64(17) . . ?
C3 C2 N1 107.2(2) . . ?
C2 C3 N2 107.6(2) . . ?
C5 C4 C9 123.2(2) . . ?
C5 C4 N1 117.9(2) . . ?
C9 C4 N1 118.9(2) . . ?
C4 C5 C6 117.2(2) . . ?
C4 C5 C10 122.2(2) . . ?
C6 C5 C10 120.5(2) . . ?
C7 C6 C5 122.0(2) . . ?
C8 C7 C6 118.1(2) . . ?
C8 C7 C11 120.6(2) . . ?
C6 C7 C11 121.3(2) . . ?
C7 C8 C9 122.8(2) . . ?
C8 C9 C4 116.7(2) . . ?
C8 C9 C12 121.1(2) . . ?
C4 C9 C12 122.3(2) . . ?
N2 C13 C14 114.63(19) . . ?
C15 C14 C19 118.9(2) . . ?
C15 C14 C13 120.3(2) . . ?
C19 C14 C13 120.7(2) . . ?
C16 C15 C14 120.8(3) . . ?
C17 C16 C15 120.2(3) . . ?
C16 C17 C18 120.3(3) . . ?
C17 C18 C19 120.0(3) . . ?
C18 C19 C14 119.7(2) . . ?
C18 C19 C20 120.5(2) . . ?
C14 C19 C20 119.8(2) . . ?
C19 C20 S1 112.36(15) . . ?
N3A C1A S2A 176.8(6) . . ?
N3B C1B S2B 176.1(13) . . ?
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 C1 1.736(2) . ?
S1 C20 1.829(2) . ?
N1 C1 1.349(3) . ?
N1 C2 1.386(3) . ?
N1 C4 1.450(3) . ?
N2 C1 1.336(3) . ?
N2 C3 1.388(3) . ?
N2 C13 1.485(3) . ?
C2 C3 1.339(3) . ?
C4 C5 1.386(3) . ?
C4 C9 1.394(3) . ?
C5 C6 1.393(3) . ?
C5 C10 1.508(3) . ?
C6 C7 1.388(3) . ?
C7 C8 1.382(3) . ?
C7 C11 1.509(3) . ?
C8 C9 1.389(3) . ?
C9 C12 1.500(3) . ?
C13 C14 1.493(3) . ?
C14 C15 1.393(4) . ?
C14 C19 1.401(3) . ?
C15 C16 1.376(4) . ?
C16 C17 1.374(4) . ?
C17 C18 1.385(4) . ?
C18 C19 1.393(3) . ?
C19 C20 1.495(3) . ?
S2A C1A 1.653(8) . ?
N3A C1A 1.161(12) . ?
C1B N3B 1.121(16) . ?
C1B S2B 1.680(11) . ?
