#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:26:14 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178469 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/90/4029070.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_4029070
loop_
_publ_author_name
'Kumar, Dhananjay'
'Mishra, Bhuwan B.'
'Tiwari, Vinod K.'
_publ_section_title
;
 Synthesis of 2-N/S/C-substituted benzothiazoles via intramolecular
 cyclative cleavage of benzotriazole ring.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              251
_journal_page_last               266
_journal_paper_doi               10.1021/jo4024107
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C13 H8 N4 S'
_chemical_formula_sum            'C13 H8 N4 S'
_chemical_formula_weight         253.32
_chemical_melting_point          175
_chemical_name_systematic
2-(1H-benzo[d][1,2,3]triazol-1-yl)benzo[d]thiazole
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   4.750(5)
_cell_length_b                   13.031(5)
_cell_length_c                   18.356(5)
_cell_measurement_reflns_used    812
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6727
_cell_measurement_theta_min      3.3112
_cell_volume                     1136.2(13)
_computing_cell_refinement       'CrysAlis Pro, Agilent Technologies'
_computing_data_collection       'CrysAlis Pro, Agilent Technologies'
_computing_data_reduction        'CrysAlis Pro, Agilent Technologies'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0938
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measurement_device_type  'XCalibur Eos, Oxford Diffraction'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0585
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3336
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.74
_diffrn_reflns_theta_min         3.32
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, Agilent Technologies Lts.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             528
_exptl_crystal_recrystallization_method 'ethyl acetate, hexane, rt, 1 atm'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2271
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0377P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1011
_reflns_number_gt                1858
_reflns_number_total             2271
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4024107_si_002.cif
_cod_data_source_block           compound_6
_cod_database_code               4029070
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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
S1 S 0.35253(17) 0.66509(6) 0.95860(4) 0.0462(2) Uani 1 1 d .
N1 N 0.7204(5) 0.67369(17) 0.84719(13) 0.0404(6) Uani 1 1 d .
N4 N 0.4770(5) 0.51794(17) 0.86724(13) 0.0403(6) Uani 1 1 d .
N2 N 0.7492(6) 0.77462(17) 0.86906(14) 0.0486(7) Uani 1 1 d .
N3 N 0.9376(6) 0.81796(18) 0.82822(15) 0.0527(7) Uani 1 1 d .
C9 C 0.9465(7) 0.5670(2) 0.74732(17) 0.0461(8) Uani 1 1 d .
H9 H 0.8525 0.5052 0.7548 0.055 Uiso 1 1 calc R
C1 C 0.1812(6) 0.5477(2) 0.96835(15) 0.0403(7) Uani 1 1 d .
C13 C 1.0336(6) 0.7460(2) 0.77845(17) 0.0414(7) Uani 1 1 d .
C6 C 0.2747(6) 0.4798(2) 0.91479(16) 0.0389(7) Uani 1 1 d .
C8 C 0.8950(6) 0.6533(2) 0.78982(15) 0.0376(7) Uani 1 1 d .
C2 C -0.0230(6) 0.5207(2) 1.01899(17) 0.0493(8) Uani 1 1 d .
H2 H -0.0841 0.5668 1.0543 0.059 Uiso 1 1 calc R
C4 C -0.0407(7) 0.3539(2) 0.96261(19) 0.0534(8) Uani 1 1 d .
H4 H -0.1176 0.2883 0.9612 0.064 Uiso 1 1 calc R
C3 C -0.1318(7) 0.4225(2) 1.01490(18) 0.0512(8) Uani 1 1 d .
H3 H -0.2691 0.4021 1.0480 0.061 Uiso 1 1 calc R
C7 C 0.5277(6) 0.6118(2) 0.88481(16) 0.0382(7) Uani 1 1 d .
C5 C 0.1625(7) 0.3810(2) 0.91238(18) 0.0501(8) Uani 1 1 d .
H5 H 0.2235 0.3342 0.8776 0.060 Uiso 1 1 calc R
C10 C 1.1447(8) 0.5788(2) 0.69385(17) 0.0542(8) Uani 1 1 d .
H10 H 1.1869 0.5229 0.6643 0.065 Uiso 1 1 calc R
C11 C 1.2868(7) 0.6716(3) 0.68154(18) 0.0573(9) Uani 1 1 d .
H11 H 1.4187 0.6757 0.6442 0.069 Uiso 1 1 calc R
C12 C 1.2345(7) 0.7564(2) 0.72366(18) 0.0518(9) Uani 1 1 d .
H12 H 1.3289 0.8180 0.7160 0.062 Uiso 1 1 calc R
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 C1 87.29(14)
C8 N1 N2 110.4(2)
C8 N1 C7 131.6(2)
N2 N1 C7 118.0(2)
C7 N4 C6 108.1(3)
N3 N2 N1 108.4(2)
N2 N3 C13 108.3(2)
C10 C9 C8 115.6(3)
C10 C9 H9 122.2
C8 C9 H9 122.2
C2 C1 C6 122.2(3)
C2 C1 S1 128.2(2)
C6 C1 S1 109.6(2)
N3 C13 C8 109.4(3)
N3 C13 C12 129.5(3)
C8 C13 C12 121.1(3)
N4 C6 C5 125.0(3)
N4 C6 C1 115.8(3)
C5 C6 C1 119.1(3)
N1 C8 C9 134.1(3)
N1 C8 C13 103.5(3)
C9 C8 C13 122.4(3)
C3 C2 C1 117.4(3)
C3 C2 H2 121.3
C1 C2 H2 121.3
C3 C4 C5 121.2(3)
C3 C4 H4 119.4
C5 C4 H4 119.4
C4 C3 C2 121.3(3)
C4 C3 H3 119.4
C2 C3 H3 119.4
N4 C7 N1 123.1(3)
N4 C7 S1 119.1(2)
N1 C7 S1 117.8(2)
C4 C5 C6 118.8(3)
C4 C5 H5 120.6
C6 C5 H5 120.6
C9 C10 C11 122.9(3)
C9 C10 H10 118.5
C11 C10 H10 118.5
C12 C11 C10 121.1(3)
C12 C11 H11 119.5
C10 C11 H11 119.5
C11 C12 C13 117.0(3)
C11 C12 H12 121.5
C13 C12 H12 121.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C7 1.735(3)
S1 C1 1.742(3)
N1 C8 1.367(3)
N1 N2 1.382(3)
N1 C7 1.402(4)
N4 C7 1.287(3)
N4 C6 1.390(4)
N2 N3 1.297(3)
N3 C13 1.386(4)
C9 C10 1.369(4)
C9 C8 1.391(4)
C9 H9 0.9300
C1 C2 1.389(4)
C1 C6 1.395(4)
C13 C8 1.391(4)
C13 C12 1.393(4)
C6 C5 1.394(4)
C2 C3 1.383(4)
C2 H2 0.9300
C4 C3 1.380(4)
C4 C5 1.381(4)
C4 H4 0.9300
C3 H3 0.9300
C5 H5 0.9300
C10 C11 1.403(5)
C10 H10 0.9300
C11 C12 1.371(4)
C11 H11 0.9300
C12 H12 0.9300
