#------------------------------------------------------------------------------
#$Date: 2016-03-21 05:29:08 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178480 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/01/4030108.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_4030108
loop_
_publ_author_name
'Chávez, Patricia'
'Ngov, Chheng'
'Frémont, Pierre de'
'Lévêque, Patrick'
'Leclerc, Nicolas'
_publ_section_title
;
 Synthesis by Direct Arylation of Thiazole-Derivatives: Regioisomer
 Configurations-Optical Properties Relationship Investigation.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10179
_journal_paper_doi               10.1021/jo501685t
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C12 H6 N4 S3'
_chemical_formula_sum            'C12 H6 N4 S3'
_chemical_formula_weight         302.39
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 97.009(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.274(2)
_cell_length_b                   11.141(3)
_cell_length_c                   12.659(4)
_cell_measurement_reflns_used    2279
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.02
_cell_measurement_theta_min      3.08
_cell_volume                     1158.2(6)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  triumph
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7814
_diffrn_reflns_theta_full        28.05
_diffrn_reflns_theta_max         28.05
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  0.9876
_exptl_absorpt_correction_T_min  0.7875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.889
_refine_diff_density_min         -0.642
_refine_diff_density_rms         0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0678
_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)+(0.1308P)²+1.3368P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2003
_refine_ls_wR_factor_ref         0.2135
_reflns_number_gt                2119
_reflns_number_total             2792
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo501685t_si_002.cif
_cod_data_source_block           cphpc130805
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 4030107--4030108.cif.
;
_cod_original_cell_volume        1158.1(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4030108
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
C1 C 0.6775(5) 0.5726(4) 0.5071(4) 0.0214(9) Uani 1 1 d .
H1 H 0.7365 0.5100 0.4781 0.026 Uiso 1 1 calc R
C2 C 0.5888(5) 0.6854(3) 0.6328(3) 0.0149(8) Uani 1 1 d .
H2 H 0.5789 0.7113 0.7032 0.018 Uiso 1 1 calc R
C3 C 0.5057(5) 0.7408(3) 0.5402(3) 0.0130(7) Uani 1 1 d .
C4 C 0.3980(5) 0.8458(3) 0.5386(3) 0.0140(8) Uani 1 1 d .
C5 C 0.3323(5) 0.9040(3) 0.4422(3) 0.0137(8) Uani 1 1 d .
C6 C 0.2292(5) 1.0086(3) 0.4415(3) 0.0130(7) Uani 1 1 d .
C7 C 0.1907(5) 1.0586(3) 0.5395(3) 0.0144(8) Uani 1 1 d .
C8 C 0.2549(5) 0.9990(4) 0.6309(3) 0.0175(8) Uani 1 1 d .
H8 H 0.2305 1.0287 0.6975 0.021 Uiso 1 1 calc R
C9 C 0.3552(5) 0.8959(4) 0.6305(3) 0.0182(8) Uani 1 1 d .
H9 H 0.3946 0.8599 0.6967 0.022 Uiso 1 1 calc R
C10 C 0.0903(5) 1.1668(3) 0.5433(3) 0.0133(8) Uani 1 1 d .
C11 C 0.0113(4) 1.2370(3) 0.4578(3) 0.0137(8) Uani 1 1 d .
H11 H 0.0145 1.2191 0.3847 0.016 Uiso 1 1 calc R
C12 C -0.0529(6) 1.3421(4) 0.5984(4) 0.0240(10) Uani 1 1 d .
H12 H -0.1000 1.4049 0.6351 0.029 Uiso 1 1 calc R
N1 N 0.6852(5) 0.5900(3) 0.6095(3) 0.0246(8) Uani 1 1 d .
N2 N 0.3574(4) 0.8688(3) 0.3425(3) 0.0182(7) Uani 1 1 d .
N3 N 0.1789(4) 1.0492(3) 0.3434(3) 0.0178(7) Uani 1 1 d .
N4 N -0.0715(5) 1.3354(3) 0.4942(3) 0.0254(9) Uani 1 1 d .
S1 S 0.55570(14) 0.66824(10) 0.42844(9) 0.0212(3) Uani 1 1 d .
S2 S 0.25801(14) 0.96199(10) 0.26125(8) 0.0224(3) Uani 1 1 d .
S3 S 0.06008(15) 1.23183(10) 0.66365(9) 0.0250(3) Uani 1 1 d .
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
N1 C1 S1 116.2(3)
N1 C1 H1 121.9
S1 C1 H1 121.9
N1 C2 C3 113.0(4)
N1 C2 H2 123.5
C3 C2 H2 123.5
C2 C3 C4 126.0(4)
C2 C3 S1 109.4(3)
C4 C3 S1 124.6(3)
C9 C4 C5 115.3(4)
C9 C4 C3 122.0(4)
C5 C4 C3 122.7(4)
N2 C5 C4 125.2(4)
N2 C5 C6 112.6(4)
C4 C5 C6 122.2(3)
N3 C6 C7 126.6(4)
N3 C6 C5 113.2(3)
C7 C6 C5 120.2(3)
C8 C7 C6 115.8(3)
C8 C7 C10 121.8(4)
C6 C7 C10 122.4(4)
C7 C8 C9 123.5(4)
C7 C8 H8 118.3
C9 C8 H8 118.3
C4 C9 C8 122.9(4)
C4 C9 H9 118.5
C8 C9 H9 118.5
C11 C10 C7 129.3(4)
C11 C10 S3 109.7(3)
C7 C10 S3 121.0(3)
N4 C11 C10 112.1(4)
N4 C11 H11 124.0
C10 C11 H11 124.0
N4 C12 S3 116.0(3)
N4 C12 H12 122.0
S3 C12 H12 122.0
C1 N1 C2 111.5(4)
C5 N2 S2 106.4(3)
C6 N3 S2 106.8(3)
C12 N4 C11 111.9(4)
C1 S1 C3 89.9(2)
N2 S2 N3 101.02(18)
C12 S3 C10 90.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.304(6)
C1 S1 1.702(4)
C1 H1 0.9500
C2 N1 1.382(5)
C2 C3 1.425(6)
C2 H2 0.9500
C3 C4 1.469(5)
C3 S1 1.723(4)
C4 C9 1.376(6)
C4 C5 1.430(6)
C5 N2 1.361(5)
C5 C6 1.444(5)
C6 N3 1.340(5)
C6 C7 1.430(5)
C7 C8 1.383(6)
C7 C10 1.468(5)
C8 C9 1.417(6)
C8 H8 0.9500
C9 H9 0.9500
C10 C11 1.428(5)
C10 S3 1.732(4)
C11 N4 1.400(5)
C11 H11 0.9500
C12 N4 1.311(6)
C12 S3 1.696(5)
C12 H12 0.9500
N2 S2 1.614(4)
N3 S2 1.619(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
N1 C2 C3 C4 -178.3(4)
N1 C2 C3 S1 -0.1(4)
C2 C3 C4 C9 -5.8(6)
S1 C3 C4 C9 176.3(3)
C2 C3 C4 C5 173.3(4)
S1 C3 C4 C5 -4.6(5)
C9 C4 C5 N2 -179.3(4)
C3 C4 C5 N2 1.5(6)
C9 C4 C5 C6 0.5(6)
C3 C4 C5 C6 -178.7(4)
N2 C5 C6 N3 0.3(5)
C4 C5 C6 N3 -179.5(3)
N2 C5 C6 C7 -179.5(3)
C4 C5 C6 C7 0.7(6)
N3 C6 C7 C8 178.8(4)
C5 C6 C7 C8 -1.4(5)
N3 C6 C7 C10 -1.5(6)
C5 C6 C7 C10 178.3(3)
C6 C7 C8 C9 1.1(6)
C10 C7 C8 C9 -178.6(4)
C5 C4 C9 C8 -0.9(6)
C3 C4 C9 C8 178.3(4)
C7 C8 C9 C4 0.1(7)
C8 C7 C10 C11 -178.1(4)
C6 C7 C10 C11 2.3(6)
C8 C7 C10 S3 5.0(5)
C6 C7 C10 S3 -174.7(3)
C7 C10 C11 N4 -179.0(4)
S3 C10 C11 N4 -1.8(4)
S1 C1 N1 C2 0.3(5)
C3 C2 N1 C1 -0.1(5)
C4 C5 N2 S2 179.8(3)
C6 C5 N2 S2 0.0(4)
C7 C6 N3 S2 179.4(3)
C5 C6 N3 S2 -0.4(4)
S3 C12 N4 C11 -1.3(5)
C10 C11 N4 C12 2.0(5)
N1 C1 S1 C3 -0.4(4)
C2 C3 S1 C1 0.3(3)
C4 C3 S1 C1 178.4(4)
C5 N2 S2 N3 -0.3(3)
C6 N3 S2 N2 0.4(3)
N4 C12 S3 C10 0.2(4)
C11 C10 S3 C12 0.9(3)
C7 C10 S3 C12 178.4(3)
