#------------------------------------------------------------------------------
#$Date: 2016-12-10 04:31:59 +0200 (Sat, 10 Dec 2016) $
#$Revision: 189043 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/47/1544772.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_1544772
loop_
_publ_author_name
'Moussaif, Ahmed'
'Ramli, Youssef'
'Sebbar, Nada Kheira'
'Essassi, El Mokhtar'
'Mague, Joel T.'
_publ_section_title
;
 2,3-Dihydrobenz[4,5]imidazo[2,1-b]thiazole
;
_journal_coeditor_code           SU4107
_journal_issue                   12
_journal_name_full               IUCrData
_journal_page_first              x161948
_journal_paper_doi               10.1107/S2414314616019489
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C9 H8 N2 S'
_chemical_formula_moiety         'C9 H8 N2 S'
_chemical_formula_sum            'C9 H8 N2 S'
_chemical_formula_weight         176.23
_chemical_name_systematic
;
2,3-Dihydrobenz[4,5]imidazo[2,1-b]thiazole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 118.2340(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.7440(8)
_cell_length_b                   11.4820(7)
_cell_length_c                   12.8707(8)
_cell_measurement_reflns_used    4421
_cell_measurement_temperature    298.(2)
_cell_measurement_theta_max      25.3501
_cell_measurement_theta_min      2.5244
_cell_volume                     1659.25(18)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012 and Mercury (Macrae et
al.,  2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15538
_diffrn_reflns_theta_full        28.000
_diffrn_reflns_theta_max         29.128
_diffrn_reflns_theta_min         1.814
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.251
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0762P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1336
_reflns_number_gt                2702
_reflns_number_total             4244
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su4107sup1.cif
_cod_data_source_block           I
_cod_database_code               1544772
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.886
_shelx_estimated_absorpt_t_max   0.981
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_occupancy
S S1 0.60928(5) 0.83270(4) 0.50755(5) 0.06186(19) Uani d 1
N N1 0.67791(13) 0.67804(12) 0.69522(13) 0.0494(4) Uani d 1
N N2 0.48777(12) 0.67647(11) 0.55018(12) 0.0423(3) Uani d 1
C C1 0.61392(15) 0.59028(14) 0.71572(15) 0.0433(4) Uani d 1
C C2 0.65137(19) 0.51054(16) 0.80769(17) 0.0530(5) Uani d 1
H H2 0.7323(17) 0.5100(17) 0.8657(17) 0.067(6) Uiso d 1
C C3 0.5701(2) 0.43030(17) 0.80575(18) 0.0571(5) Uani d 1
H H3 0.5961(19) 0.375(2) 0.8645(19) 0.076(6) Uiso d 1
C C4 0.4535(2) 0.42874(17) 0.71608(19) 0.0585(5) Uani d 1
H H4 0.3984(17) 0.3748(19) 0.7162(17) 0.067(6) Uiso d 1
C C5 0.41276(17) 0.50738(16) 0.62405(17) 0.0503(4) Uani d 1
H H5 0.3330(18) 0.5108(18) 0.5642(16) 0.064(6) Uiso d 1
C C6 0.49469(14) 0.58756(13) 0.62549(14) 0.0408(4) Uani d 1
C C7 0.59884(15) 0.72369(15) 0.59596(15) 0.0442(4) Uani d 1
C C8 0.40008(17) 0.71382(17) 0.43372(16) 0.0489(4) Uani d 1
H H8A 0.3903(15) 0.6550(16) 0.3759(15) 0.047(5) Uiso d 1
H H8B 0.3277(17) 0.7257(16) 0.4307(15) 0.054(5) Uiso d 1
C C9 0.4497(2) 0.8251(2) 0.4088(2) 0.0637(6) Uani d 1
H H9A 0.435(2) 0.8278(18) 0.330(2) 0.080(7) Uiso d 1
H H9B 0.4210(19) 0.895(2) 0.4243(19) 0.084(8) Uiso d 1
S S2 0.09273(5) 0.81657(5) 0.59932(5) 0.06511(19) Uani d 1
N N3 0.14754(13) 0.66410(13) 0.46357(14) 0.0531(4) Uani d 1
N N4 -0.03893(13) 0.66826(12) 0.43993(13) 0.0447(3) Uani d 1
C C10 0.07636(16) 0.58368(15) 0.37754(16) 0.0480(4) Uani d 1
C C11 0.1060(2) 0.50724(18) 0.31224(19) 0.0605(5) Uani d 1
H H11 0.1862(18) 0.5015(17) 0.3240(16) 0.066(6) Uiso d 1
C C12 0.0190(2) 0.43527(18) 0.2334(2) 0.0686(6) Uani d 1
H H12 0.0374(18) 0.384(2) 0.1871(18) 0.073(6) Uiso d 1
C C13 -0.0963(2) 0.43830(19) 0.2175(2) 0.0716(6) Uani d 1
H H13 -0.152(2) 0.389(2) 0.166(2) 0.091(8) Uiso d 1
C C14 -0.12870(19) 0.51306(18) 0.28185(18) 0.0591(5) Uani d 1
H H14 -0.203(2) 0.512(2) 0.2730(19) 0.084(7) Uiso d 1
C C15 -0.04071(15) 0.58468(14) 0.36185(15) 0.0442(4) Uani d 1
C C16 0.07387(15) 0.71029(15) 0.49625(15) 0.0469(4) Uani d 1
C C17 -0.12433(18) 0.71370(19) 0.47270(19) 0.0520(5) Uani d 1
H H17A -0.1465(16) 0.6577(16) 0.5092(16) 0.053(5) Uiso d 1
H H17B -0.1870(19) 0.740(2) 0.4091(19) 0.075(7) Uiso d 1
C C18 -0.0634(2) 0.8086(3) 0.5617(3) 0.0783(7) Uani d 1
H H18A -0.070(3) 0.805(3) 0.625(3) 0.131(13) Uiso d 1
H H18B -0.094(3) 0.885(3) 0.530(3) 0.140(13) Uiso d 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'
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
C7 S1 C9 90.94(9)
C7 N1 C1 103.00(14)
C7 N2 C6 106.40(14)
C7 N2 C8 117.73(14)
C6 N2 C8 135.01(15)
C2 C1 N1 129.76(17)
C2 C1 C6 119.26(17)
N1 C1 C6 110.98(15)
C3 C2 C1 118.20(19)
C3 C2 H2 122.7(12)
C1 C2 H2 119.0(12)
C2 C3 C4 121.65(19)
C2 C3 H3 118.0(14)
C4 C3 H3 120.3(14)
C5 C4 C3 121.78(19)
C5 C4 H4 117.1(13)
C3 C4 H4 121.1(13)
C4 C5 C6 116.60(18)
C4 C5 H5 123.5(12)
C6 C5 H5 119.8(12)
N2 C6 C5 133.16(16)
N2 C6 C1 104.34(14)
C5 C6 C1 122.50(16)
N1 C7 N2 115.25(15)
N1 C7 S1 131.83(14)
N2 C7 S1 112.90(13)
N2 C8 C9 105.81(16)
N2 C8 H8A 110.2(11)
C9 C8 H8A 109.8(10)
N2 C8 H8B 110.9(11)
C9 C8 H8B 112.1(12)
H8A C8 H8B 108.1(15)
C8 C9 S1 109.29(15)
C8 C9 H9A 111.2(14)
S1 C9 H9A 109.9(14)
C8 C9 H9B 115.4(14)
S1 C9 H9B 103.2(13)
H9A C9 H9B 107.5(19)
C16 S2 C18 91.29(10)
C16 N3 C10 103.12(14)
C16 N4 C15 106.52(14)
C16 N4 C17 118.16(15)
C15 N4 C17 135.30(15)
C11 C10 N3 129.68(18)
C11 C10 C15 119.51(18)
N3 C10 C15 110.80(15)
C12 C11 C10 118.3(2)
C12 C11 H11 120.2(12)
C10 C11 H11 121.5(12)
C11 C12 C13 121.7(2)
C11 C12 H12 119.2(13)
C13 C12 H12 119.1(13)
C12 C13 C14 121.5(2)
C12 C13 H13 119.9(17)
C14 C13 H13 118.5(17)
C15 C14 C13 116.7(2)
C15 C14 H14 122.5(15)
C13 C14 H14 120.7(15)
C14 C15 N4 133.23(17)
C14 C15 C10 122.31(17)
N4 C15 C10 104.46(15)
N3 C16 N4 115.10(16)
N3 C16 S2 132.09(14)
N4 C16 S2 112.81(13)
N4 C17 C18 107.23(17)
N4 C17 H17A 110.8(12)
C18 C17 H17A 107.0(12)
N4 C17 H17B 109.3(14)
C18 C17 H17B 111.7(15)
H17A C17 H17B 110.8(18)
C17 C18 S2 110.27(16)
C17 C18 H18A 116(2)
S2 C18 H18A 109(2)
C17 C18 H18B 112(2)
S2 C18 H18B 104.2(19)
H18A C18 H18B 104(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C7 1.7385(18)
S1 C9 1.821(3)
N1 C7 1.305(2)
N1 C1 1.398(2)
N2 C7 1.362(2)
N2 C6 1.381(2)
N2 C8 1.447(2)
C1 C2 1.390(3)
C1 C6 1.410(2)
C2 C3 1.378(3)
C2 H2 0.945(19)
C3 C4 1.384(3)
C3 H3 0.92(2)
C4 C5 1.381(3)
C4 H4 0.94(2)
C5 C6 1.386(2)
C5 H5 0.942(19)
C8 C9 1.525(3)
C8 H8A 0.968(18)
C8 H8B 0.915(19)
C9 H9A 0.94(2)
C9 H9B 0.94(2)
S2 C16 1.7336(18)
S2 C18 1.813(3)
N3 C16 1.309(2)
N3 C10 1.397(2)
N4 C16 1.356(2)
N4 C15 1.382(2)
N4 C17 1.438(2)
C10 C11 1.385(3)
C10 C15 1.408(2)
C11 C12 1.370(3)
C11 H11 0.961(19)
C12 C13 1.385(3)
C12 H12 0.94(2)
C13 C14 1.385(3)
C13 H13 0.90(2)
C14 C15 1.379(3)
C14 H14 0.90(2)
C17 C18 1.503(3)
C17 H17A 0.917(19)
C17 H17B 0.88(2)
C18 H18A 0.85(3)
C18 H18B 0.97(3)
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
C8 H8B N3 . 0.92(2) 2.62(2) 3.464(2) 154(2)
C8 H8A Cg3 3_666 0.97(2) 2.65(2) 3.543(2) 154(2)
C9 H9A Cg3 4_575 0.94(2) 2.99(2) 3.661(3) 129(2)
C12 H12 Cg7 2_545 0.94(2) 2.94(2) 3.838(2) 161(2)
C18 H18A Cg9 4_576 0.85(3) 2.90(3) 3.471(4) 126(3)
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
C7 N1 C1 C2 179.00(17)
C7 N1 C1 C6 -0.63(17)
N1 C1 C2 C3 -178.60(17)
C6 C1 C2 C3 1.0(2)
C1 C2 C3 C4 -0.8(3)
C2 C3 C4 C5 0.0(3)
C3 C4 C5 C6 0.4(3)
C7 N2 C6 C5 -178.18(18)
C8 N2 C6 C5 -9.5(3)
C7 N2 C6 C1 1.27(16)
C8 N2 C6 C1 169.95(17)
C4 C5 C6 N2 179.21(17)
C4 C5 C6 C1 -0.2(3)
C2 C1 C6 N2 179.90(14)
N1 C1 C6 N2 -0.42(17)
C2 C1 C6 C5 -0.6(2)
N1 C1 C6 C5 179.10(15)
C1 N1 C7 N2 1.54(18)
C1 N1 C7 S1 -176.53(14)
C6 N2 C7 N1 -1.88(19)
C8 N2 C7 N1 -172.86(15)
C6 N2 C7 S1 176.57(11)
C8 N2 C7 S1 5.59(19)
C9 S1 C7 N1 -176.19(18)
C9 S1 C7 N2 5.70(14)
C7 N2 C8 C9 -16.1(2)
C6 N2 C8 C9 176.18(18)
N2 C8 C9 S1 18.9(2)
C7 S1 C9 C8 -14.46(17)
C16 N3 C10 C11 -178.96(19)
C16 N3 C10 C15 -0.18(19)
N3 C10 C11 C12 179.12(18)
C15 C10 C11 C12 0.4(3)
C10 C11 C12 C13 0.5(3)
C11 C12 C13 C14 -1.0(4)
C12 C13 C14 C15 0.4(3)
C13 C14 C15 N4 -179.87(19)
C13 C14 C15 C10 0.6(3)
C16 N4 C15 C14 180.0(2)
C17 N4 C15 C14 1.7(3)
C16 N4 C15 C10 -0.44(18)
C17 N4 C15 C10 -178.74(19)
C11 C10 C15 C14 -1.0(3)
N3 C10 C15 C14 -179.95(17)
C11 C10 C15 N4 179.32(16)
N3 C10 C15 N4 0.40(18)
C10 N3 C16 N4 -0.1(2)
C10 N3 C16 S2 179.86(15)
C15 N4 C16 N3 0.4(2)
C17 N4 C16 N3 179.02(16)
C15 N4 C16 S2 -179.61(11)
C17 N4 C16 S2 -1.0(2)
C18 S2 C16 N3 178.1(2)
C18 S2 C16 N4 -1.92(17)
C16 N4 C17 C18 4.0(3)
C15 N4 C17 C18 -177.8(2)
N4 C17 C18 S2 -5.1(3)
C16 S2 C18 C17 4.1(2)

_cod_database_fobs_code 1544772
