#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/56/4025683.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_4025683
loop_
_publ_author_name
'Xiaoxiang Zhang'
'Wan Teng Teo'
Sally
'Philip Wai Hong Chan'
_publ_section_title
;
 Brønsted Acid Catalyzed Cyclization of Propargylic Alcohols with
 Thioamides. Facile Synthesis of Di- and Trisubstituted Thiazoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6290
_journal_page_last               6293
_journal_paper_doi               10.1021/jo101292r
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C23 H19 N S'
_chemical_formula_sum            'C23 H19 N S'
_chemical_formula_weight         341.45
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.473(3)
_cell_angle_beta                 92.291(2)
_cell_angle_gamma                116.375(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6709(3)
_cell_length_b                   10.2215(4)
_cell_length_c                   10.6585(6)
_cell_measurement_reflns_used    7070
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.64
_cell_measurement_theta_min      2.38
_cell_volume                     881.65(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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_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  0.0560
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17503
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.9355
_exptl_absorpt_correction_T_min  0.9287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0630
_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)+(0.1910P)²+0.2406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1952
_refine_ls_wR_factor_ref         0.2512
_reflns_number_gt                3383
_reflns_number_total             4087
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101292r_si_002.cif
_cod_data_source_block           chan67t
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025683
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3892(3) 0.7631(3) -0.0080(3) 0.0345(6) Uani 1 1 d . . .
H1A H 0.4864 0.8583 0.0444 0.052 Uiso 1 1 calc R . .
H1B H 0.3466 0.7792 -0.0836 0.052 Uiso 1 1 calc R . .
H1C H 0.4122 0.6761 -0.0420 0.052 Uiso 1 1 calc R . .
C2 C 0.2716(3) 0.7263(2) 0.0792(2) 0.0220(5) Uani 1 1 d . . .
C3 C 0.1529(2) 0.6493(2) 0.2375(2) 0.0173(4) Uani 1 1 d . . .
C4 C 0.0555(2) 0.7013(2) 0.1984(2) 0.0186(4) Uani 1 1 d . . .
C5 C 0.1308(2) 0.5714(2) 0.3412(2) 0.0166(4) Uani 1 1 d . . .
H5 H 0.0384 0.5739 0.3786 0.020 Uiso 1 1 calc R . .
C6 C 0.2711(2) 0.6624(2) 0.4594(2) 0.0176(4) Uani 1 1 d . . .
C7 C 0.3385(2) 0.8249(2) 0.5164(2) 0.0222(5) Uani 1 1 d . . .
H7 H 0.3010 0.8781 0.4770 0.027 Uiso 1 1 calc R . .
C8 C 0.4585(3) 0.9097(2) 0.6290(2) 0.0264(5) Uani 1 1 d . . .
H8 H 0.5015 1.0200 0.6669 0.032 Uiso 1 1 calc R . .
C9 C 0.5164(3) 0.8349(3) 0.6866(3) 0.0313(6) Uani 1 1 d . . .
H9 H 0.6000 0.8933 0.7632 0.038 Uiso 1 1 calc R . .
C10 C 0.4513(3) 0.6737(3) 0.6313(3) 0.0312(5) Uani 1 1 d . . .
H10 H 0.4906 0.6216 0.6703 0.037 Uiso 1 1 calc R . .
C11 C 0.3298(3) 0.5883(3) 0.5200(2) 0.0236(5) Uani 1 1 d . . .
H11 H 0.2853 0.4778 0.4842 0.028 Uiso 1 1 calc R . .
C12 C 0.0871(2) 0.4000(2) 0.2780(2) 0.0181(4) Uani 1 1 d . . .
C13 C -0.0579(3) 0.2861(2) 0.2838(2) 0.0228(5) Uani 1 1 d . . .
H13 H -0.1306 0.3161 0.3235 0.027 Uiso 1 1 calc R . .
C14 C -0.0986(3) 0.1281(3) 0.2322(3) 0.0300(5) Uani 1 1 d . . .
H14 H -0.1969 0.0514 0.2393 0.036 Uiso 1 1 calc R . .
C15 C 0.0048(3) 0.0838(3) 0.1707(3) 0.0304(5) Uani 1 1 d . . .
H15 H -0.0223 -0.0235 0.1352 0.037 Uiso 1 1 calc R . .
C16 C 0.1487(3) 0.1968(3) 0.1610(2) 0.0278(5) Uani 1 1 d . . .
H16 H 0.2191 0.1662 0.1177 0.033 Uiso 1 1 calc R . .
C17 C 0.1897(2) 0.3535(2) 0.2142(2) 0.0224(5) Uani 1 1 d . . .
H17 H 0.2882 0.4299 0.2072 0.027 Uiso 1 1 calc R . .
C18 C -0.0810(2) 0.7103(2) 0.2490(2) 0.0200(5) Uani 1 1 d . . .
C19 C -0.0723(3) 0.7773(3) 0.3859(3) 0.0261(5) Uani 1 1 d . . .
H19 H 0.0216 0.8145 0.4481 0.031 Uiso 1 1 calc R . .
C20 C -0.1999(3) 0.7902(3) 0.4324(3) 0.0349(6) Uani 1 1 d . . .
H20 H -0.1933 0.8349 0.5259 0.042 Uiso 1 1 calc R . .
C21 C -0.3365(3) 0.7379(3) 0.3421(3) 0.0374(6) Uani 1 1 d . . .
H21 H -0.4231 0.7476 0.3738 0.045 Uiso 1 1 calc R . .
C22 C -0.3469(3) 0.6717(3) 0.2067(3) 0.0361(6) Uani 1 1 d . . .
H22 H -0.4411 0.6354 0.1452 0.043 Uiso 1 1 calc R . .
C23 C -0.2206(3) 0.6578(3) 0.1592(3) 0.0286(5) Uani 1 1 d . . .
H23 H -0.2287 0.6126 0.0655 0.034 Uiso 1 1 calc R . .
N1 N 0.2753(2) 0.6650(2) 0.16980(19) 0.0199(4) Uani 1 1 d . . .
S1 S 0.11813(6) 0.76781(6) 0.06907(5) 0.0237(2) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C1 124.8(2) . . ?
N1 C2 S1 114.37(17) . . ?
C1 C2 S1 120.85(18) . . ?
C4 C3 N1 115.32(18) . . ?
C4 C3 C5 125.24(18) . . ?
N1 C3 C5 119.37(17) . . ?
C3 C4 C18 131.4(2) . . ?
C3 C4 S1 108.86(15) . . ?
C18 C4 S1 119.71(15) . . ?
C3 C5 C12 111.87(16) . . ?
C3 C5 C6 112.17(16) . . ?
C12 C5 C6 113.10(16) . . ?
C3 C5 H5 106.4 . . ?
C12 C5 H5 106.4 . . ?
C6 C5 H5 106.4 . . ?
C7 C6 C11 117.70(19) . . ?
C7 C6 C5 119.78(18) . . ?
C11 C6 C5 122.37(18) . . ?
C8 C7 C6 121.3(2) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 120.3(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C10 119.3(2) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C6 120.8(2) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
C13 C12 C17 118.79(19) . . ?
C13 C12 C5 119.53(18) . . ?
C17 C12 C5 121.68(18) . . ?
C12 C13 C14 120.9(2) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 119.9(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C12 120.4(2) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C19 C18 C23 118.4(2) . . ?
C19 C18 C4 121.06(19) . . ?
C23 C18 C4 120.4(2) . . ?
C20 C19 C18 120.7(2) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C19 120.0(3) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C20 120.1(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 120.4(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 120.4(3) . . ?
C22 C23 H23 119.8 . . ?
C18 C23 H23 119.8 . . ?
C2 N1 C3 111.25(18) . . ?
C2 S1 C4 90.18(10) . . ?
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
C1 C2 1.488(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.306(3) . ?
C2 S1 1.723(2) . ?
C3 C4 1.375(3) . ?
C3 N1 1.384(3) . ?
C3 C5 1.516(3) . ?
C4 C18 1.475(3) . ?
C4 S1 1.730(2) . ?
C5 C12 1.521(3) . ?
C5 C6 1.527(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.398(3) . ?
C6 C11 1.400(3) . ?
C7 C8 1.381(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.387(3) . ?
C12 C17 1.397(3) . ?
C13 C14 1.397(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.394(3) . ?
C18 C23 1.405(3) . ?
C19 C20 1.393(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.376(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.388(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659269
