#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/90/2229063.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_2229063
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Yeap, Chin Sing'
'Prasad, D. Jagadeesh'
'Castelino, Prakash Anil'
'Anitha, V. V.'
_publ_section_title
;
 2-Isobutyl-6-(4-methoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazole
;
_journal_coeditor_code           HB5778
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o255
_journal_paper_doi               10.1107/S1600536810053225
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H17 N3 O S'
_chemical_formula_moiety         'C15 H17 N3 O S'
_chemical_formula_sum            'C15 H17 N3 O S'
_chemical_formula_weight         287.38
_chemical_name_systematic
;
2-Isobutyl-6-(4-methoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazole
;
_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                85.1740(10)
_cell_angle_beta                 85.1640(10)
_cell_angle_gamma                80.6900(10)
_cell_formula_units_Z            2
_cell_length_a                   5.71390(10)
_cell_length_b                   10.17950(10)
_cell_length_c                   12.9689(2)
_cell_measurement_reflns_used    6150
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.14
_cell_measurement_theta_min      2.48
_cell_volume                     739.837(19)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEXII 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  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23503
_diffrn_reflns_theta_full        34.50
_diffrn_reflns_theta_max         34.50
_diffrn_reflns_theta_min         1.58
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.9635
_exptl_absorpt_correction_T_min  0.9113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.280
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         6213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0530
_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)+(0.0765P)²+0.0748P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1631
_reflns_number_gt                3805
_reflns_number_total             6213
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5778.cif
_cod_data_source_block           I
_cod_database_code               2229063
_cod_database_fobs_code          2229063
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 1.14439(6) 1.02701(4) 0.26563(3) 0.05911(14) Uani d . 1 . .
O O1 1.1085(2) 0.33486(12) 0.78317(9) 0.0741(3) Uani d . 1 . .
N N1 0.7031(2) 1.05243(12) 0.33719(9) 0.0523(3) Uani d . 1 . .
N N2 0.82991(18) 0.94641(11) 0.39100(8) 0.0448(2) Uani d . 1 . .
N N3 1.16801(18) 0.81311(11) 0.42311(8) 0.0470(2) Uani d . 1 . .
C C1 1.2380(2) 0.58244(13) 0.57132(10) 0.0459(3) Uani d . 1 . .
H H1A 1.3637 0.6030 0.5258 0.055 Uiso calc R 1 . .
C C2 1.2769(3) 0.47212(13) 0.64264(10) 0.0498(3) Uani d . 1 . .
H H2A 1.4261 0.4199 0.6442 0.060 Uiso calc R 1 . .
C C3 1.0917(3) 0.44125(14) 0.71078(10) 0.0515(3) Uani d . 1 . .
C C4 0.8704(3) 0.52078(17) 0.70788(12) 0.0620(4) Uani d . 1 . .
H H4A 0.7456 0.5008 0.7542 0.074 Uiso calc R 1 . .
C C5 0.8345(2) 0.62946(16) 0.63658(12) 0.0541(3) Uani d . 1 . .
H H5A 0.6852 0.6817 0.6354 0.065 Uiso calc R 1 . .
C C6 1.0186(2) 0.66223(12) 0.56621(9) 0.0405(2) Uani d . 1 . .
C C7 0.9808(2) 0.77580(12) 0.48936(9) 0.0397(2) Uani d . 1 . .
C C8 0.7710(2) 0.85747(13) 0.47028(10) 0.0497(3) Uani d . 1 . .
H H8A 0.6217 0.8533 0.5038 0.060 Uiso calc R 1 . .
C C9 0.8461(2) 1.10357(13) 0.26920(10) 0.0473(3) Uani d . 1 . .
C C10 1.0665(2) 0.91576(13) 0.36590(9) 0.0441(3) Uani d . 1 . .
C C11 0.7678(3) 1.22647(14) 0.20133(11) 0.0571(4) Uani d . 1 . .
H H11A 0.8370 1.2992 0.2240 0.069 Uiso calc R 1 . .
H H11B 0.5965 1.2493 0.2123 0.069 Uiso calc R 1 . .
C C12 0.8305(3) 1.21810(16) 0.08633(11) 0.0642(4) Uani d . 1 . .
H H12A 1.0026 1.1905 0.0754 0.077 Uiso calc R 1 . .
C C13 0.7083(6) 1.1178(2) 0.04179(17) 0.1097(9) Uani d . 1 . .
H H13A 0.7482 1.0322 0.0783 0.165 Uiso calc R 1 . .
H H13B 0.7594 1.1119 -0.0303 0.165 Uiso calc R 1 . .
H H13C 0.5393 1.1455 0.0489 0.165 Uiso calc R 1 . .
C C14 0.7663(6) 1.3557(2) 0.03141(17) 0.1117(9) Uani d . 1 . .
H H14A 0.8461 1.4183 0.0607 0.167 Uiso calc R 1 . .
H H14B 0.5975 1.3836 0.0400 0.167 Uiso calc R 1 . .
H H14C 0.8148 1.3522 -0.0411 0.167 Uiso calc R 1 . .
C C15 1.3354(4) 0.25718(19) 0.79377(16) 0.0840(6) Uani d . 1 . .
H H15A 1.3233 0.1863 0.8467 0.126 Uiso calc R 1 . .
H H15B 1.4436 0.3125 0.8127 0.126 Uiso calc R 1 . .
H H15C 1.3931 0.2200 0.7291 0.126 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 S1 C9 . . 88.40(6) ?
C3 O1 C15 . . 117.66(14) ?
C9 N1 N2 . . 108.55(11) ?
C10 N2 C8 . . 107.69(10) ?
C10 N2 N1 . . 118.51(11) ?
C8 N2 N1 . . 133.79(11) ?
C10 N3 C7 . . 103.73(10) ?
C6 C1 C2 . . 122.09(12) ?
C6 C1 H1A . . 119.0 ?
C2 C1 H1A . . 119.0 ?
C3 C2 C1 . . 119.33(13) ?
C3 C2 H2A . . 120.3 ?
C1 C2 H2A . . 120.3 ?
O1 C3 C2 . . 124.39(14) ?
O1 C3 C4 . . 115.99(14) ?
C2 C3 C4 . . 119.62(13) ?
C5 C4 C3 . . 120.36(14) ?
C5 C4 H4A . . 119.8 ?
C3 C4 H4A . . 119.8 ?
C4 C5 C6 . . 121.14(14) ?
C4 C5 H5A . . 119.4 ?
C6 C5 H5A . . 119.4 ?
C1 C6 C5 . . 117.46(12) ?
C1 C6 C7 . . 121.12(11) ?
C5 C6 C7 . . 121.42(11) ?
C8 C7 N3 . . 111.03(11) ?
C8 C7 C6 . . 127.62(11) ?
N3 C7 C6 . . 121.35(10) ?
N2 C8 C7 . . 104.79(11) ?
N2 C8 H8A . . 127.6 ?
C7 C8 H8A . . 127.6 ?
N1 C9 C11 . . 122.38(13) ?
N1 C9 S1 . . 116.15(10) ?
C11 C9 S1 . . 121.36(11) ?
N3 C10 N2 . . 112.76(11) ?
N3 C10 S1 . . 138.85(10) ?
N2 C10 S1 . . 108.39(9) ?
C9 C11 C12 . . 116.36(12) ?
C9 C11 H11A . . 108.2 ?
C12 C11 H11A . . 108.2 ?
C9 C11 H11B . . 108.2 ?
C12 C11 H11B . . 108.2 ?
H11A C11 H11B . . 107.4 ?
C13 C12 C11 . . 112.03(16) ?
C13 C12 C14 . . 110.67(17) ?
C11 C12 C14 . . 109.10(15) ?
C13 C12 H12A . . 108.3 ?
C11 C12 H12A . . 108.3 ?
C14 C12 H12A . . 108.3 ?
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 ?
C12 C14 H14A . . 109.5 ?
C12 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C12 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
O1 C15 H15A . . 109.5 ?
O1 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O1 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C10 . 1.7290(13) ?
S1 C9 . 1.7545(14) ?
O1 C3 . 1.3690(16) ?
O1 C15 . 1.416(2) ?
N1 C9 . 1.2864(19) ?
N1 N2 . 1.3721(14) ?
N2 C10 . 1.3554(16) ?
N2 C8 . 1.3689(16) ?
N3 C10 . 1.3133(15) ?
N3 C7 . 1.3957(16) ?
C1 C6 . 1.3825(17) ?
C1 C2 . 1.3947(17) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.379(2) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.388(2) ?
C4 C5 . 1.381(2) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.3967(18) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.4622(16) ?
C7 C8 . 1.3722(17) ?
C8 H8A . 0.9300 ?
C9 C11 . 1.4966(18) ?
C11 C12 . 1.510(2) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.503(3) ?
C12 C14 . 1.521(2) ?
C12 H12A . 0.9800 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 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
_geom_hbond_publ_flag
C11 H11A Cg3 2_776 0.97 2.60 3.5063(16) 155 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N1 N2 C10 . . . . 0.23(17) ?
C9 N1 N2 C8 . . . . 179.94(14) ?
C6 C1 C2 C3 . . . . -0.3(2) ?
C15 O1 C3 C2 . . . . 4.8(2) ?
C15 O1 C3 C4 . . . . -175.43(15) ?
C1 C2 C3 O1 . . . . 179.30(13) ?
C1 C2 C3 C4 . . . . -0.4(2) ?
O1 C3 C4 C5 . . . . -179.11(14) ?
C2 C3 C4 C5 . . . . 0.7(2) ?
C3 C4 C5 C6 . . . . -0.2(2) ?
C2 C1 C6 C5 . . . . 0.7(2) ?
C2 C1 C6 C7 . . . . -178.73(12) ?
C4 C5 C6 C1 . . . . -0.5(2) ?
C4 C5 C6 C7 . . . . 178.95(13) ?
C10 N3 C7 C8 . . . . -0.10(14) ?
C10 N3 C7 C6 . . . . 179.31(11) ?
C1 C6 C7 C8 . . . . 175.00(13) ?
C5 C6 C7 C8 . . . . -4.5(2) ?
C1 C6 C7 N3 . . . . -4.31(18) ?
C5 C6 C7 N3 . . . . 176.24(12) ?
C10 N2 C8 C7 . . . . 0.06(15) ?
N1 N2 C8 C7 . . . . -179.67(13) ?
N3 C7 C8 N2 . . . . 0.03(15) ?
C6 C7 C8 N2 . . . . -179.34(11) ?
N2 N1 C9 C11 . . . . -176.23(11) ?
N2 N1 C9 S1 . . . . -0.04(15) ?
C10 S1 C9 N1 . . . . -0.10(12) ?
C10 S1 C9 C11 . . . . 176.13(11) ?
C7 N3 C10 N2 . . . . 0.14(15) ?
C7 N3 C10 S1 . . . . -179.92(13) ?
C8 N2 C10 N3 . . . . -0.13(16) ?
N1 N2 C10 N3 . . . . 179.65(11) ?
C8 N2 C10 S1 . . . . 179.92(9) ?
N1 N2 C10 S1 . . . . -0.31(15) ?
C9 S1 C10 N3 . . . . -179.73(16) ?
C9 S1 C10 N2 . . . . 0.21(10) ?
N1 C9 C11 C12 . . . . -129.32(16) ?
S1 C9 C11 C12 . . . . 54.69(18) ?
C9 C11 C12 C13 . . . . 64.3(2) ?
C9 C11 C12 C14 . . . . -172.81(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12158219
