#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/00/2220057.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2220057
loop_
_publ_author_name
'Chen, Xiao-Bao'
'Sun, Feng-Mei'
'Xu, Jing'
'Ma, Zuan'
'Zheng, Ai-Hua'
_publ_section_title
;Ethyl
 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-5-methyl-1H-1,2,3-triazole-4-carboxylate
;
_journal_coeditor_code           AT2677
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2402
_journal_page_last               o2403
_journal_paper_doi               10.1107/S1600536808037914
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C10 H11 Cl N4 O2 S'
_chemical_formula_moiety         'C10 H11 Cl N4 O2 S'
_chemical_formula_sum            'C10 H11 Cl N4 O2 S'
_chemical_formula_weight         286.74
_chemical_name_systematic
;
Ethyl 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-5-methyl-1H-1,2,3-
triazole-4-carboxylate
;
_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                65.892(2)
_cell_angle_beta                 67.938(2)
_cell_angle_gamma                80.641(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9692(14)
_cell_length_b                   9.1656(16)
_cell_length_c                   10.4430(18)
_cell_measurement_reflns_used    2592
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.43
_cell_volume                     645.2(2)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL  (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_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  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4630
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.43
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.457
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.253
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2332
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0408
_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)+(0.0620P)²+0.2829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1178
_reflns_number_gt                2005
_reflns_number_total             2332
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2677.cif
_cod_data_source_block           I
_cod_original_cell_volume        645.23(19)
_cod_database_code               2220057
_cod_database_fobs_code          2220057
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Cl Cl1 -0.01266(10) 0.69136(8) 0.20124(9) 0.0704(2) Uani d . 1
S S1 0.23526(8) 0.46808(7) 0.07021(7) 0.0534(2) Uani d . 1
O O1 0.7825(3) -0.0891(2) 0.3892(2) 0.0715(5) Uani d . 1
O O2 0.5259(3) -0.2272(2) 0.5002(2) 0.0718(6) Uani d . 1
N N1 -0.0923(3) 0.4021(3) 0.2475(3) 0.0674(6) Uani d . 1
N N2 0.4074(3) 0.0929(2) 0.1275(2) 0.0486(5) Uani d . 1
N N3 0.5752(3) 0.1573(3) 0.0531(2) 0.0603(5) Uani d . 1
N N4 0.6709(3) 0.0880(2) 0.1400(2) 0.0567(5) Uani d . 1
C C1 0.0281(3) 0.5109(3) 0.1813(3) 0.0496(5) Uani d . 1
C C2 -0.0196(4) 0.2725(3) 0.2086(3) 0.0676(7) Uani d . 1
H H2 -0.0873 0.1816 0.2446 0.081 Uiso calc R 1
C C3 0.1528(3) 0.2836(3) 0.1165(3) 0.0479(5) Uani d . 1
C C4 0.2660(4) 0.1603(3) 0.0601(3) 0.0584(6) Uani d . 1
H H4A 0.1887 0.0750 0.0830 0.070 Uiso calc R 1
H H4B 0.3222 0.2087 -0.0476 0.070 Uiso calc R 1
C C5 0.3935(3) -0.0189(2) 0.2639(2) 0.0419(5) Uani d . 1
C C6 0.5634(3) -0.0210(2) 0.2704(2) 0.0435(5) Uani d . 1
C C7 0.2239(3) -0.1066(3) 0.3707(3) 0.0611(7) Uani d . 1
H H7A 0.1451 -0.0411 0.4214 0.092 Uiso calc R 1
H H7B 0.2521 -0.2038 0.4424 0.092 Uiso calc R 1
H H7C 0.1648 -0.1314 0.3172 0.092 Uiso calc R 1
C C8 0.6388(3) -0.1135(3) 0.3903(3) 0.0472(5) Uani d . 1
C C9 0.5797(5) -0.3295(3) 0.6289(4) 0.0808(9) Uani d . 1
H H9A 0.6961 -0.2958 0.6163 0.097 Uiso calc R 1
H H9B 0.4914 -0.3195 0.7191 0.097 Uiso calc R 1
C C10 0.5916(6) -0.4920(4) 0.6429(4) 0.1001(13) Uani d . 1
H H10A 0.4813 -0.5209 0.6427 0.150 Uiso calc R 1
H H10B 0.6104 -0.5599 0.7349 0.150 Uiso calc R 1
H H10C 0.6913 -0.5045 0.5605 0.150 Uiso calc R 1
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'
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
C1 S1 C3 88.37(12)
C8 O2 C9 118.2(2)
C1 N1 C2 108.7(2)
C5 N2 N3 111.70(19)
C5 N2 C4 129.3(2)
N3 N2 C4 118.8(2)
N4 N3 N2 107.38(18)
N3 N4 C6 108.2(2)
N1 C1 Cl1 122.4(2)
N1 C1 S1 116.79(19)
Cl1 C1 S1 120.83(14)
C3 C2 N1 117.0(2)
C3 C2 H2 121.5
N1 C2 H2 121.5
C2 C3 C4 128.2(2)
C2 C3 S1 109.13(19)
C4 C3 S1 122.70(19)
N2 C4 C3 111.66(18)
N2 C4 H4A 109.3
C3 C4 H4A 109.3
N2 C4 H4B 109.3
C3 C4 H4B 109.3
H4A C4 H4B 107.9
N2 C5 C6 103.16(19)
N2 C5 C7 123.2(2)
C6 C5 C7 133.6(2)
N4 C6 C5 109.60(19)
N4 C6 C8 119.0(2)
C5 C6 C8 131.4(2)
C5 C7 H7A 109.5
C5 C7 H7B 109.5
H7A C7 H7B 109.5
C5 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
O1 C8 O2 124.3(2)
O1 C8 C6 124.5(2)
O2 C8 C6 111.18(18)
C10 C9 O2 110.0(3)
C10 C9 H9A 109.7
O2 C9 H9A 109.7
C10 C9 H9B 109.7
O2 C9 H9B 109.7
H9A C9 H9B 108.2
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.715(2)
S1 C1 1.717(2)
S1 C3 1.726(2)
O1 C8 1.197(3)
O2 C8 1.328(3)
O2 C9 1.464(3)
N1 C1 1.281(3)
N1 C2 1.380(4)
N2 C5 1.349(3)
N2 N3 1.357(3)
N2 C4 1.470(3)
N3 N4 1.304(3)
N4 C6 1.370(3)
C2 C3 1.340(4)
C2 H2 0.9300
C3 C4 1.501(3)
C4 H4A 0.9700
C4 H4B 0.9700
C5 C6 1.378(3)
C5 C7 1.485(3)
C6 C8 1.476(3)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C9 C10 1.427(5)
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C2 H2 O1 1_455 0.93 2.47 3.375(4) 164.00
C7 H7B O2 . 0.96 2.43 3.033(4) 121.00
C9 H9A O1 . 0.97 2.28 2.710(4) 106.00
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
C5 N2 N3 N4 0.1(3)
C4 N2 N3 N4 174.52(19)
N2 N3 N4 C6 -0.1(3)
C2 N1 C1 Cl1 179.52(19)
C2 N1 C1 S1 -0.5(3)
C3 S1 C1 N1 0.1(2)
C3 S1 C1 Cl1 -179.93(15)
C1 N1 C2 C3 0.8(4)
N1 C2 C3 C4 178.2(2)
N1 C2 C3 S1 -0.8(3)
C1 S1 C3 C2 0.38(19)
C1 S1 C3 C4 -178.66(19)
C5 N2 C4 C3 78.7(3)
N3 N2 C4 C3 -94.6(3)
C2 C3 C4 N2 -109.0(3)
S1 C3 C4 N2 69.9(3)
N3 N2 C5 C6 -0.1(2)
C4 N2 C5 C6 -173.8(2)
N3 N2 C5 C7 178.8(2)
C4 N2 C5 C7 5.1(3)
N3 N4 C6 C5 0.0(3)
N3 N4 C6 C8 -178.4(2)
N2 C5 C6 N4 0.0(2)
C7 C5 C6 N4 -178.6(2)
N2 C5 C6 C8 178.2(2)
C7 C5 C6 C8 -0.4(4)
C9 O2 C8 O1 0.2(4)
C9 O2 C8 C6 -179.5(2)
N4 C6 C8 O1 8.3(3)
C5 C6 C8 O1 -169.7(2)
N4 C6 C8 O2 -171.9(2)
C5 C6 C8 O2 10.0(3)
C8 O2 C9 C10 -119.0(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741192
