#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/48/2234880.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_2234880
loop_
_publ_author_name
'Li, Chen'
'Yu, Guang Yan'
'Tian, Xin'
'Li, Song'
'Xiao, Tao'
_publ_section_title
;
 7-Diethylamino-2-propylsulfanyl-3-(1H-1,2,4-triazol-1-yl)-4H-thiochromen-4-one
;
_journal_coeditor_code           ZQ2162
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1435
_journal_paper_doi               10.1107/S1600536812015954
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C18 H22 N4 O S2'
_chemical_formula_moiety         'C18 H22 N4 O S2'
_chemical_formula_sum            'C18 H22 N4 O S2'
_chemical_formula_weight         374.52
_chemical_melting_point          420
_chemical_name_systematic
;
7-Diethylamino-2-propylsulfanyl-3-(1H-1,2,4-triazol-1-yl)-4H-
thiochromen-4-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 109.85(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.937(4)
_cell_length_b                   9.817(2)
_cell_length_c                   19.059(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     3860.6(15)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0623
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3644
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.97
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.9444
_exptl_absorpt_correction_T_min  0.9183
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.288
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3549
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0623
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+2.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1603
_refine_ls_wR_factor_ref         0.1805
_reflns_number_gt                2309
_reflns_number_total             3549
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            zq2162.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2234880
_cod_database_fobs_code          2234880
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y,1/2-z
-x,-y,-z
x,-y,1/2+z
1/2+x,1/2+y,z
1/2-x,1/2+y,1/2-z
1/2-x,1/2-y,-z
1/2+x,1/2-y,1/2+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
_atom_site_symmetry_multiplicity
O O 0.31273(13) 0.6959(3) -0.19491(12) 0.0685(7) Uani d . 1 1
S S1 0.37800(5) 0.93494(9) 0.01442(4) 0.0623(3) Uani d . 1 1
C C1 0.34042(17) 0.7137(3) 0.06581(16) 0.0521(8) Uani d . 1 1
H H1A 0.3504 0.7653 0.1092 0.063 Uiso calc R 1 1
N N1 0.31682(18) 0.5173(3) 0.12929(16) 0.0768(10) Uani d U 1 1
S S2 0.42593(6) 1.12341(11) -0.07537(6) 0.0778(4) Uani d . 1 1
N N2 0.37390(13) 0.9341(3) -0.19835(14) 0.0517(7) Uani d . 1 1
C C2 0.31990(18) 0.5786(4) 0.06550(18) 0.0575(9) Uani d . 1 1
C C3 0.3029(2) 0.5069(4) -0.00294(19) 0.0647(10) Uani d . 1 1
H H3A 0.2884 0.4175 -0.0051 0.078 Uiso calc R 1 1
N N3 0.42763(15) 0.9017(4) -0.21445(17) 0.0755(10) Uani d . 1 1
C C4 0.30731(19) 0.5662(3) -0.06570(17) 0.0591(9) Uani d . 1 1
H H4A 0.2953 0.5160 -0.1097 0.071 Uiso calc R 1 1
N N4 0.35895(17) 1.0243(4) -0.30789(17) 0.0752(10) Uani d . 1 1
C C5 0.32941(15) 0.7002(3) -0.06632(15) 0.0460(7) Uani d . 1 1
C C6 0.34602(15) 0.7712(3) 0.00137(16) 0.0461(7) Uani d . 1 1
C C7 0.33381(16) 0.7573(3) -0.13516(16) 0.0498(8) Uani d . 1 1
C C8 0.36498(16) 0.8890(3) -0.13097(16) 0.0496(8) Uani d . 1 1
C C9 0.38666(17) 0.9716(3) -0.07033(17) 0.0521(8) Uani d . 1 1
C C10 0.3179(3) 0.3638(5) 0.1353(3) 0.0961(15) Uani d U 1 1
H H10A 0.3371 0.3251 0.1009 0.115 Uiso calc R 1 1
H H10B 0.3439 0.3366 0.1855 0.115 Uiso calc R 1 1
C C11 0.2543(3) 0.3150(7) 0.1184(3) 0.122(2) Uani d . 1 1
H H11A 0.2550 0.2174 0.1222 0.184 Uiso calc R 1 1
H H11B 0.2288 0.3414 0.0685 0.184 Uiso calc R 1 1
H H11C 0.2356 0.3527 0.1529 0.184 Uiso calc R 1 1
C C12 0.3326(2) 0.5939(5) 0.1989(2) 0.0825(13) Uani d . 1 1
H H12A 0.3115 0.5512 0.2304 0.099 Uiso calc R 1 1
H H12B 0.3154 0.6856 0.1878 0.099 Uiso calc R 1 1
C C13 0.4041(3) 0.6019(6) 0.2407(3) 0.126(2) Uani d . 1 1
H H13A 0.4117 0.6538 0.2856 0.189 Uiso calc R 1 1
H H13B 0.4253 0.6454 0.2101 0.189 Uiso calc R 1 1
H H13C 0.4212 0.5117 0.2533 0.189 Uiso calc R 1 1
C C14 0.4445(2) 1.1997(4) 0.0179(2) 0.0828(13) Uani d . 1 1
H H14A 0.4048 1.2114 0.0289 0.099 Uiso calc R 1 1
H H14B 0.4727 1.1394 0.0552 0.099 Uiso calc R 1 1
C C15 0.4759(3) 1.3310(5) 0.0208(3) 0.1027(16) Uani d . 1 1
H H15A 0.4476 1.3907 -0.0167 0.123 Uiso calc R 1 1
H H15B 0.5155 1.3188 0.0095 0.123 Uiso calc R 1 1
C C16 0.4921(3) 1.3968(5) 0.0972(3) 0.1077(17) Uani d . 1 1
H H16A 0.5126 1.4832 0.0972 0.162 Uiso calc R 1 1
H H16B 0.5209 1.3387 0.1343 0.162 Uiso calc R 1 1
H H16C 0.4529 1.4102 0.1082 0.162 Uiso calc R 1 1
C C17 0.4160(2) 0.9580(5) -0.2799(2) 0.0791(13) Uani d . 1 1
H H17A 0.4453 0.9527 -0.3056 0.095 Uiso calc R 1 1
C C18 0.33441(19) 1.0072(4) -0.25448(18) 0.0632(10) Uani d . 1 1
H H18A 0.2946 1.0417 -0.2556 0.076 Uiso calc R 1 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C9 S1 C6 103.07(15) no
C6 C1 C2 120.3(3) ?
C6 C1 H1A 119.9 ?
C2 C1 H1A 119.9 ?
C2 N1 C12 120.6(3) no
C2 N1 C10 119.8(3) no
C12 N1 C10 116.9(3) ?
C9 S2 C14 104.25(17) no
C18 N2 N3 108.8(3) no
C18 N2 C8 129.4(3) no
N3 N2 C8 121.7(3) no
N1 C2 C1 121.4(3) no
N1 C2 C3 121.3(3) no
C1 C2 C3 117.3(3) ?
C4 C3 C2 121.4(3) ?
C4 C3 H3A 119.3 ?
C2 C3 H3A 119.3 ?
C17 N3 N2 102.4(3) no
C3 C4 C5 122.4(3) ?
C3 C4 H4A 118.8 ?
C5 C4 H4A 118.8 ?
C18 N4 C17 101.6(3) no
C6 C5 C4 116.2(3) ?
C6 C5 C7 124.1(3) ?
C4 C5 C7 119.7(3) ?
C1 C6 C5 122.4(3) ?
C1 C6 S1 113.6(2) no
C5 C6 S1 123.9(2) no
O C7 C8 120.6(3) no
O C7 C5 121.6(3) no
C8 C7 C5 117.8(3) ?
C9 C8 N2 117.6(3) no
C9 C8 C7 126.9(3) ?
N2 C8 C7 115.5(3) no
C8 C9 S1 123.6(3) no
C8 C9 S2 120.1(3) no
S1 C9 S2 116.33(18) no
C11 C10 N1 109.5(5) no
C11 C10 H10A 109.8 ?
N1 C10 H10A 109.8 ?
C11 C10 H10B 109.8 ?
N1 C10 H10B 109.8 ?
H10A C10 H10B 108.2 ?
C10 C11 H11A 109.5 ?
C10 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
C10 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
N1 C12 C13 113.0(4) no
N1 C12 H12A 109.0 ?
C13 C12 H12A 109.0 ?
N1 C12 H12B 109.0 ?
C13 C12 H12B 109.0 ?
H12A C12 H12B 107.8 ?
C12 C13 H13A 109.5 ?
C12 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C12 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
C15 C14 S2 110.1(3) no
C15 C14 H14A 109.6 ?
S2 C14 H14A 109.6 ?
C15 C14 H14B 109.6 ?
S2 C14 H14B 109.6 ?
H14A C14 H14B 108.2 ?
C14 C15 C16 111.5(4) ?
C14 C15 H15A 109.3 ?
C16 C15 H15A 109.3 ?
C14 C15 H15B 109.3 ?
C16 C15 H15B 109.3 ?
H15A C15 H15B 108.0 ?
C15 C16 H16A 109.5 ?
C15 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C15 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
N3 C17 N4 115.7(3) no
N3 C17 H17A 122.1 ?
N4 C17 H17A 122.1 ?
N4 C18 N2 111.4(3) no
N4 C18 H18A 124.3 ?
N2 C18 H18A 124.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O C7 1.231(4) no
S1 C9 1.727(3) no
S1 C6 1.738(3) no
C1 C6 1.394(4) ?
C1 C2 1.400(5) ?
C1 H1A 0.9300 ?
N1 C2 1.378(4) no
N1 C12 1.460(5) no
N1 C10 1.512(6) no
S2 C9 1.740(3) no
S2 C14 1.843(4) no
N2 C18 1.335(4) no
N2 N3 1.353(4) no
N2 C8 1.433(4) no
C2 C3 1.416(5) ?
C3 C4 1.363(4) ?
C3 H3A 0.9300 ?
N3 C17 1.308(4) no
C4 C5 1.404(4) ?
C4 H4A 0.9300 ?
N4 C18 1.314(4) no
N4 C17 1.350(5) no
C5 C6 1.401(4) ?
C5 C7 1.460(4) ?
C7 C8 1.452(5) ?
C8 C9 1.358(4) ?
C10 C11 1.405(7) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 H11A 0.9600 ?
C11 H11B 0.9600 ?
C11 H11C 0.9600 ?
C12 C13 1.502(7) ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
C14 C15 1.454(6) ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
C15 C16 1.520(6) ?
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
C16 H16A 0.9600 ?
C16 H16B 0.9600 ?
C16 H16C 0.9600 ?
C17 H17A 0.9300 ?
C18 H18A 0.9300 ?
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
_geom_hbond_publ_flag
C1 H1A N4 4_575 0.9300 2.5700 3.451(5) 159.00 yes
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
C12 N1 C2 C1 2.4(6)
C10 N1 C2 C1 -158.5(4)
C12 N1 C2 C3 -178.1(4)
C10 N1 C2 C3 21.0(6)
C6 C1 C2 N1 177.0(3)
C6 C1 C2 C3 -2.5(5)
N1 C2 C3 C4 -178.5(4)
C1 C2 C3 C4 1.0(6)
C18 N2 N3 C17 -0.3(4)
C8 N2 N3 C17 178.4(3)
C2 C3 C4 C5 0.7(6)
C3 C4 C5 C6 -0.8(5)
C3 C4 C5 C7 179.2(4)
C2 C1 C6 C5 2.5(5)
C2 C1 C6 S1 -175.3(3)
C4 C5 C6 C1 -0.7(5)
C7 C5 C6 C1 179.2(3)
C4 C5 C6 S1 176.8(3)
C7 C5 C6 S1 -3.2(5)
C9 S1 C6 C1 174.2(3)
C9 S1 C6 C5 -3.6(3)
C6 C5 C7 O -172.8(3)
C4 C5 C7 O 7.2(5)
C6 C5 C7 C8 8.2(5)
C4 C5 C7 C8 -171.9(3)
C18 N2 C8 C9 -90.9(4)
N3 N2 C8 C9 90.7(4)
C18 N2 C8 C7 89.7(4)
N3 N2 C8 C7 -88.7(4)
O C7 C8 C9 175.5(3)
C5 C7 C8 C9 -5.4(5)
O C7 C8 N2 -5.1(5)
C5 C7 C8 N2 173.9(3)
N2 C8 C9 S1 178.3(2)
C7 C8 C9 S1 -2.3(5)
N2 C8 C9 S2 -2.0(4)
C7 C8 C9 S2 177.4(3)
C6 S1 C9 C8 6.2(4)
C6 S1 C9 S2 -173.5(2)
C14 S2 C9 C8 179.0(3)
C14 S2 C9 S1 -1.2(3)
C2 N1 C10 C11 -98.6(5)
C12 N1 C10 C11 99.8(5)
C2 N1 C12 C13 -82.1(5)
C10 N1 C12 C13 79.4(5)
C9 S2 C14 C15 -178.2(4)
S2 C14 C15 C16 -179.9(4)
N2 N3 C17 N4 -0.1(5)
C18 N4 C17 N3 0.5(5)
C17 N4 C18 N2 -0.6(5)
N3 N2 C18 N4 0.6(5)
C8 N2 C18 N4 -177.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657726
