#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/56/4025684.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_4025684
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         'C25 H22 Cl N S'
_chemical_formula_sum            'C25 H22 Cl N S'
_chemical_formula_weight         403.95
_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                101.725(6)
_cell_angle_beta                 100.635(6)
_cell_angle_gamma                115.204(5)
_cell_formula_units_Z            2
_cell_length_a                   9.6923(11)
_cell_length_b                   10.0308(11)
_cell_length_c                   12.2838(14)
_cell_measurement_reflns_used    6064
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      31.25
_cell_measurement_theta_min      2.37
_cell_volume                     1007.3(2)
_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      103(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20530
_diffrn_reflns_theta_full        31.91
_diffrn_reflns_theta_max         31.91
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  0.9417
_exptl_absorpt_correction_T_min  0.9306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         6850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0484
_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)+(0.1021P)²+0.0466P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1415
_refine_ls_wR_factor_ref         0.1707
_reflns_number_gt                4990
_reflns_number_total             6850
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101292r_si_003.cif
_cod_data_source_block           chan75s
_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               4025684
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 0.73014(18) 0.33861(17) 0.03528(14) 0.0158(3) Uani 1 1 d . . .
C2 C 0.65131(19) 0.17765(17) -0.01844(15) 0.0187(3) Uani 1 1 d . . .
H2 H 0.6904 0.1165 0.0123 0.022 Uiso 1 1 calc R . .
C3 C 0.5178(2) 0.10640(18) -0.11536(15) 0.0213(3) Uani 1 1 d . . .
H3 H 0.4663 -0.0030 -0.1509 0.026 Uiso 1 1 calc R . .
C4 C 0.4579(2) 0.1937(2) -0.16154(15) 0.0235(3) Uani 1 1 d . . .
H4 H 0.3660 0.1444 -0.2284 0.028 Uiso 1 1 calc R . .
C5 C 0.5337(2) 0.35310(19) -0.10899(15) 0.0221(3) Uani 1 1 d . . .
H5 H 0.4933 0.4134 -0.1398 0.027 Uiso 1 1 calc R . .
C6 C 0.6688(2) 0.42535(18) -0.01135(14) 0.0187(3) Uani 1 1 d . . .
H6 H 0.7199 0.5348 0.0240 0.022 Uiso 1 1 calc R . .
C7 C 0.88604(19) 0.41519(17) 0.13602(14) 0.0162(3) Uani 1 1 d . . .
H7 H 0.9701 0.4128 0.1004 0.019 Uiso 1 1 calc R . .
C8 C 0.94346(18) 0.58604(17) 0.19877(14) 0.0159(3) Uani 1 1 d . . .
C9 C 0.8649(2) 0.63411(18) 0.26873(15) 0.0205(3) Uani 1 1 d . . .
H9 H 0.7698 0.5592 0.2772 0.025 Uiso 1 1 calc R . .
C10 C 0.9244(2) 0.79043(19) 0.32609(16) 0.0230(3) Uani 1 1 d . . .
H10 H 0.8699 0.8219 0.3738 0.028 Uiso 1 1 calc R . .
C11 C 1.0637(2) 0.90201(19) 0.31433(17) 0.0245(4) Uani 1 1 d . . .
H11 H 1.1052 1.0089 0.3550 0.029 Uiso 1 1 calc R . .
C12 C 1.1410(2) 0.85590(18) 0.24308(16) 0.0240(4) Uani 1 1 d . . .
H12 H 1.2346 0.9313 0.2332 0.029 Uiso 1 1 calc R . .
C13 C 1.0814(2) 0.69899(18) 0.18610(15) 0.0194(3) Uani 1 1 d . . .
H13 H 1.1353 0.6679 0.1377 0.023 Uiso 1 1 calc R . .
C14 C 0.87788(18) 0.32443(17) 0.22115(14) 0.0159(3) Uani 1 1 d . . .
C15 C 0.97830(19) 0.26477(17) 0.25017(14) 0.0177(3) Uani 1 1 d . . .
C16 C 1.10580(19) 0.25774(17) 0.20268(15) 0.0184(3) Uani 1 1 d . . .
C17 C 1.0773(2) 0.20367(18) 0.08263(16) 0.0206(3) Uani 1 1 d . . .
H17 H 0.9765 0.1744 0.0301 0.025 Uiso 1 1 calc R . .
C18 C 1.1966(2) 0.19257(19) 0.03961(17) 0.0249(4) Uani 1 1 d . . .
H18 H 1.1765 0.1558 -0.0423 0.030 Uiso 1 1 calc R . .
C19 C 1.3444(2) 0.2346(2) 0.11488(18) 0.0283(4) Uani 1 1 d . . .
H19 H 1.4250 0.2263 0.0848 0.034 Uiso 1 1 calc R . .
C20 C 1.3737(2) 0.2888(2) 0.23472(18) 0.0265(4) Uani 1 1 d . . .
H20 H 1.4749 0.3184 0.2868 0.032 Uiso 1 1 calc R . .
C21 C 1.2549(2) 0.29978(19) 0.27848(17) 0.0236(4) Uani 1 1 d . . .
H21 H 1.2753 0.3361 0.3605 0.028 Uiso 1 1 calc R . .
C22 C 0.7808(2) 0.23170(18) 0.35592(15) 0.0195(3) Uani 1 1 d . . .
C23 C 0.6778(2) 0.19286(19) 0.43438(15) 0.0221(3) Uani 1 1 d . . .
H23A H 0.6859 0.1106 0.4635 0.026 Uiso 1 1 calc R . .
H23B H 0.5646 0.1521 0.3891 0.026 Uiso 1 1 calc R . .
C24 C 0.7280(2) 0.3344(2) 0.53747(15) 0.0246(4) Uani 1 1 d . . .
H24A H 0.8409 0.3742 0.5828 0.030 Uiso 1 1 calc R . .
H24B H 0.7217 0.4171 0.5079 0.030 Uiso 1 1 calc R . .
C25 C 0.6246(2) 0.2997(2) 0.61773(16) 0.0252(4) Uani 1 1 d . . .
H25A H 0.6730 0.3902 0.6894 0.030 Uiso 1 1 calc R . .
H25B H 0.6212 0.2097 0.6409 0.030 Uiso 1 1 calc R . .
N1 N 0.76568(16) 0.30408(15) 0.28014(12) 0.0171(3) Uani 1 1 d . . .
S1 S 0.93306(5) 0.18461(5) 0.35978(4) 0.02131(12) Uani 1 1 d . . .
Cl1 Cl 0.42467(6) 0.25779(7) 0.54813(5) 0.03945(15) 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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 118.14(15) . . ?
C6 C1 C7 122.14(13) . . ?
C2 C1 C7 119.54(13) . . ?
C3 C2 C1 121.03(15) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.47(15) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.31(16) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.33(15) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.72(15) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C14 C7 C8 111.40(13) . . ?
C14 C7 C1 112.35(12) . . ?
C8 C7 C1 113.54(12) . . ?
C14 C7 H7 106.3 . . ?
C8 C7 H7 106.3 . . ?
C1 C7 H7 106.3 . . ?
C9 C8 C13 118.53(14) . . ?
C9 C8 C7 122.80(14) . . ?
C13 C8 C7 118.67(14) . . ?
C10 C9 C8 120.46(15) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.49(16) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 119.58(16) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 119.74(16) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C8 121.17(16) . . ?
C12 C13 H13 119.4 . . ?
C8 C13 H13 119.4 . . ?
C15 C14 N1 115.79(14) . . ?
C15 C14 C7 125.58(15) . . ?
N1 C14 C7 118.56(13) . . ?
C14 C15 C16 131.12(15) . . ?
C14 C15 S1 108.72(12) . . ?
C16 C15 S1 120.14(12) . . ?
C17 C16 C21 119.06(16) . . ?
C17 C16 C15 120.75(15) . . ?
C21 C16 C15 120.14(15) . . ?
C18 C17 C16 120.01(17) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 120.83(17) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 119.46(17) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C19 C20 C21 120.08(17) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 120.56(17) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
N1 C22 C23 124.23(15) . . ?
N1 C22 S1 114.19(13) . . ?
C23 C22 S1 121.58(12) . . ?
C22 C23 C24 111.45(14) . . ?
C22 C23 H23A 109.3 . . ?
C24 C23 H23A 109.3 . . ?
C22 C23 H23B 109.3 . . ?
C24 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
C25 C24 C23 112.82(14) . . ?
C25 C24 H24A 109.0 . . ?
C23 C24 H24A 109.0 . . ?
C25 C24 H24B 109.0 . . ?
C23 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C24 C25 Cl1 111.49(13) . . ?
C24 C25 H25A 109.3 . . ?
Cl1 C25 H25A 109.3 . . ?
C24 C25 H25B 109.3 . . ?
Cl1 C25 H25B 109.3 . . ?
H25A C25 H25B 108.0 . . ?
C22 N1 C14 111.04(13) . . ?
C22 S1 C15 90.24(8) . . ?
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 C6 1.399(2) . ?
C1 C2 1.399(2) . ?
C1 C7 1.530(2) . ?
C2 C3 1.379(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C14 1.511(2) . ?
C7 C8 1.528(2) . ?
C7 H7 1.0000 . ?
C8 C9 1.392(2) . ?
C8 C13 1.398(2) . ?
C9 C10 1.385(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.396(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.374(2) . ?
C14 N1 1.382(2) . ?
C15 C16 1.482(2) . ?
C15 S1 1.7347(17) . ?
C16 C17 1.394(2) . ?
C16 C21 1.399(2) . ?
C17 C18 1.393(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.392(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 N1 1.315(2) . ?
C22 C23 1.501(2) . ?
C22 S1 1.7264(17) . ?
C23 C24 1.520(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.518(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 Cl1 1.7923(19) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659270
