#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/38/2013869.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_2013869
loop_
_publ_author_name
'Viktor Kettmann '
'Jan Lokaj '
'Jozef Kožíšek '
'Josef Přikryl '
'Vladimír Macháček '
_publ_section_title
;
 3-Butyl-1-(5-nitrobenzo[c][1,2]thiazol-3-yl)-3-phenyltriazene
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o143
_journal_page_last               o145
_journal_paper_doi               10.1107/S0108270103029433
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C17 H17 N5 O2 S'
_chemical_formula_moiety         'C17 H17 N5 O2 S'
_chemical_formula_sum            'C17 H17 N5 O2 S'
_chemical_formula_weight         355.42
_chemical_melting_point          399
_chemical_name_systematic
;
3-Butyl-1-(5-nitrobenzo[c][1,2]thiazol-3-yl)-3-phenyltriazene
;
_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
_cell_angle_alpha                83.24(5)
_cell_angle_beta                 79.72(4)
_cell_angle_gamma                72.92(4)
_cell_formula_units_Z            2
_cell_length_a                   9.702(5)
_cell_length_b                   9.750(5)
_cell_length_c                   10.106(6)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      7
_cell_volume                     897.0(9)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction Ltd, 2003'
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction Ltd, 2001'
;
_computing_data_reduction
;
CrysAlis RED'
;
_computing_molecular_graphics    'ORTEPII (Johnson, 1976) '
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 'Sapphire CCD detector'
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device       'Oxford Diffraction Xcalibur CCD '
_diffrn_measurement_method
;
Rotation method data acquisition using omega and phi 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  0.0194
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6600
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         2.79
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         1127
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3993
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1631
_refine_ls_R_factor_gt           0.0667
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0613P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1634
_reflns_number_gt                2017
_reflns_number_total             3993
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1691.cif
_cod_data_source_block           Ia
_cod_database_code               2013869
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
N1 0.3368(3) 0.5051(3) 0.3631(3) 0.0598(9) Uani d . 1 . . N
S2 0.22366(10) 0.45907(11) 0.28394(10) 0.0565(3) Uani d . 1 . . S
C3 0.0691(3) 0.5813(3) 0.3510(3) 0.0407(8) Uani d . 1 . . C
C4 0.0161(4) 0.7698(4) 0.5196(3) 0.0468(9) Uani d . 1 . . C
H4 -0.0842 0.8007 0.5200 0.056 Uiso calc R 1 . . H
C5 0.0812(4) 0.8285(4) 0.5983(3) 0.0492(9) Uani d . 1 . . C
C6 0.2333(4) 0.7867(4) 0.6005(4) 0.0535(10) Uani d . 1 . . C
H6 0.2728 0.8331 0.6531 0.064 Uiso calc R 1 . . H
C7 0.3199(4) 0.6803(4) 0.5268(4) 0.0546(10) Uani d . 1 . . C
H7 0.4194 0.6498 0.5312 0.065 Uiso calc R 1 . . H
C8 0.2599(4) 0.6124(4) 0.4404(3) 0.0484(9) Uani d . 1 . . C
C9 0.1055(3) 0.6613(3) 0.4382(3) 0.0401(8) Uani d . 1 . . C
N2 -0.0082(4) 0.9397(4) 0.6866(3) 0.0667(9) Uani d . 1 . . N
O1 -0.1407(4) 0.9619(4) 0.7007(3) 0.0989(11) Uani d . 1 . . O
O2 0.0523(3) 1.0062(3) 0.7411(3) 0.0881(10) Uani d . 1 . . O
N3 -0.0715(3) 0.6045(3) 0.3234(3) 0.0420(7) Uani d . 1 . . N
N4 -0.0740(3) 0.5117(3) 0.2430(3) 0.0434(7) Uani d . 1 . . N
N5 -0.2047(3) 0.5258(3) 0.2118(3) 0.0458(7) Uani d . 1 . . N
C10 -0.2098(4) 0.4242(4) 0.1233(3) 0.0477(9) Uani d . 1 . . C
C11 -0.0832(4) 0.3365(4) 0.0587(3) 0.0570(10) Uani d . 1 . . C
H11 0.0067 0.3460 0.0691 0.068 Uiso calc R 1 . . H
C12 -0.0900(4) 0.2347(4) -0.0214(4) 0.0612(11) Uani d . 1 . . C
H12 -0.0038 0.1756 -0.0642 0.073 Uiso calc R 1 . . H
C13 -0.2190(5) 0.2185(5) -0.0393(4) 0.0709(12) Uani d . 1 . . C
H13 -0.2226 0.1487 -0.0928 0.085 Uiso calc R 1 . . H
C14 -0.3440(5) 0.3079(5) 0.0236(4) 0.0759(13) Uani d . 1 . . C
H14 -0.4335 0.2993 0.0104 0.091 Uiso calc R 1 . . H
C15 -0.3420(4) 0.4105(4) 0.1058(4) 0.0628(11) Uani d . 1 . . C
H15 -0.4286 0.4692 0.1486 0.075 Uiso calc R 1 . . H
C16 -0.3312(4) 0.6387(4) 0.2664(4) 0.0580(10) Uani d D 1 A . C
H16A -0.3220 0.6521 0.3577 0.070 Uiso calc R 1 . . H
H16B -0.4184 0.6081 0.2704 0.070 Uiso calc R 1 . . H
C17 -0.3480(4) 0.7801(4) 0.1840(5) 0.0844(14) Uani d D 1 . . C
H17A -0.3426 0.7630 0.0904 0.101 Uiso calc PR 0.527(9) A 1 H
H17B -0.2660 0.8157 0.1900 0.101 Uiso calc PR 0.527(9) A 1 H
H17C -0.3883 0.7787 0.1032 0.101 Uiso calc PR 0.473(9) A 2 H
H17D -0.2546 0.8010 0.1582 0.101 Uiso calc PR 0.473(9) A 2 H
C18 -0.4867(9) 0.8959(13) 0.2239(12) 0.098(4) Uani d PDU 0.527(9) A 1 C
H18A -0.5054 0.9665 0.1485 0.118 Uiso calc PR 0.527(9) A 1 H
H18B -0.5676 0.8537 0.2457 0.118 Uiso calc PR 0.527(9) A 1 H
C19 -0.4770(14) 0.9693(14) 0.3436(12) 0.138(5) Uani d PDU 0.527(9) A 1 C
H19A -0.5112 0.9201 0.4251 0.208 Uiso calc PR 0.527(9) A 1 H
H19B -0.5362 1.0672 0.3386 0.208 Uiso calc PR 0.527(9) A 1 H
H19C -0.3774 0.9673 0.3433 0.208 Uiso calc PR 0.527(9) A 1 H
C18' -0.4510(16) 0.8901(11) 0.2752(12) 0.117(5) Uani d PDU 0.473(9) A 2 C
H18C -0.5408 0.8626 0.3029 0.141 Uiso calc PR 0.473(9) A 2 H
H18D -0.4081 0.8865 0.3556 0.141 Uiso calc PR 0.473(9) A 2 H
C19' -0.4889(14) 1.0431(10) 0.2160(15) 0.131(5) Uani d PDU 0.473(9) A 2 C
H19D -0.4049 1.0788 0.2050 0.197 Uiso calc PR 0.473(9) A 2 H
H19E -0.5669 1.1015 0.2753 0.197 Uiso calc PR 0.473(9) A 2 H
H19F -0.5189 1.0467 0.1298 0.197 Uiso calc PR 0.473(9) A 2 H
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
C8 N1 S2 108.5(2) ?
N1 S2 C3 96.41(16) yes
N3 C3 C9 123.7(3) yes
N3 C3 S2 127.3(2) yes
C9 C3 S2 108.9(2) yes
C5 C4 C9 117.7(3) ?
C5 C4 H4 121.2 ?
C9 C4 H4 121.2 ?
C4 C5 C6 123.5(3) ?
C4 C5 N2 119.5(3) ?
C6 C5 N2 117.0(3) ?
C7 C6 C5 119.7(3) ?
C7 C6 H6 120.2 ?
C5 C6 H6 120.2 ?
C6 C7 C8 120.3(3) ?
C6 C7 H7 119.8 ?
C8 C7 H7 119.8 ?
N1 C8 C9 116.9(3) ?
N1 C8 C7 125.1(3) ?
C9 C8 C7 118.0(3) ?
C3 C9 C4 130.1(3) ?
C3 C9 C8 109.2(3) ?
C4 C9 C8 120.7(3) ?
O2 N2 O1 123.7(4) ?
O2 N2 C5 118.7(4) ?
O1 N2 C5 117.6(3) ?
N4 N3 C3 110.3(3) yes
N3 N4 N5 114.3(3) yes
N4 N5 C10 115.1(3) yes
N4 N5 C16 120.6(3) yes
C10 N5 C16 124.2(3) yes
C15 C10 C11 119.6(3) ?
C15 C10 N5 119.7(3) ?
C11 C10 N5 120.7(3) ?
C12 C11 C10 120.0(3) ?
C12 C11 H11 120.0 ?
C10 C11 H11 120.0 ?
C13 C12 C11 121.5(4) ?
C13 C12 H12 119.2 ?
C11 C12 H12 119.2 ?
C12 C13 C14 118.0(4) ?
C12 C13 H13 121.0 ?
C14 C13 H13 121.0 ?
C13 C14 C15 122.3(4) ?
C13 C14 H14 118.9 ?
C15 C14 H14 118.9 ?
C10 C15 C14 118.6(4) ?
C10 C15 H15 120.7 ?
C14 C15 H15 120.7 ?
N5 C16 C17 113.0(3) ?
N5 C16 H16A 109.0 ?
C17 C16 H16A 109.0 ?
N5 C16 H16B 109.0 ?
C17 C16 H16B 109.0 ?
H16A C16 H16B 107.8 ?
C16 C17 C18 115.7(7) ?
C16 C17 C18' 104.9(6) ?
C16 C17 H17A 108.4 ?
C18 C17 H17A 108.4 ?
C18' C17 H17A 133.0 ?
C16 C17 H17B 108.4 ?
C18 C17 H17B 108.4 ?
C18' C17 H17B 92.1 ?
H17A C17 H17B 107.4 ?
C16 C17 H17C 110.8 ?
C18 C17 H17C 85.4 ?
C18' C17 H17C 110.8 ?
H17B C17 H17C 126.7 ?
C16 C17 H17D 110.8 ?
C18 C17 H17D 121.9 ?
C18' C17 H17D 110.8 ?
H17A C17 H17D 87.2 ?
H17C C17 H17D 108.8 ?
C19 C18 C17 111.4(7) ?
C19 C18 H18A 109.3 ?
C17 C18 H18A 109.3 ?
C19 C18 H18B 109.3 ?
C17 C18 H18B 109.3 ?
H18A C18 H18B 108.0 ?
C19' C18' C17 116.0(9) ?
C19' C18' H18C 108.3 ?
C17 C18' H18C 108.3 ?
C19' C18' H18D 108.3 ?
C17 C18' H18D 108.3 ?
H18C C18' H18D 107.4 ?
C18' C19' H19D 109.5 ?
C18' C19' H19E 109.5 ?
H19D C19' H19E 109.5 ?
C18' C19' H19F 109.5 ?
H19D C19' H19F 109.5 ?
H19E C19' H19F 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
N1 C8 . 1.337(4) yes
N1 S2 . 1.653(3) yes
S2 C3 . 1.705(3) yes
C3 N3 . 1.390(4) yes
C3 C9 . 1.394(4) yes
C4 C5 . 1.363(4) yes
C4 C9 . 1.400(4) yes
C4 H4 . 0.9300 ?
C5 C6 . 1.415(5) yes
C5 N2 . 1.457(5) yes
C6 C7 . 1.335(5) yes
C6 H6 . 0.9300 ?
C7 C8 . 1.443(5) yes
C7 H7 . 0.9300 ?
C8 C9 . 1.436(4) yes
N2 O2 . 1.221(4) ?
N2 O1 . 1.224(4) ?
N3 N4 . 1.293(3) yes
N4 N5 . 1.325(3) yes
N5 C10 . 1.426(4) yes
N5 C16 . 1.459(4) yes
C10 C15 . 1.372(4) ?
C10 C11 . 1.376(5) ?
C11 C12 . 1.374(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.352(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.367(5) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.381(5) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 C17 . 1.506(4) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 C18 . 1.506(4) ?
C17 C18' . 1.508(5) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C17 H17C . 0.9700 ?
C17 H17D . 0.9700 ?
C18 C19 . 1.505(5) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
C18' C19' . 1.505(5) ?
C18' H18C . 0.9700 ?
C18' H18D . 0.9700 ?
C19' H19D . 0.9600 ?
C19' H19E . 0.9600 ?
C19' H19F . 0.9600 ?
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
_geom_torsion_publ_flag
C8 N1 S2 C3 0.0(3) ?
N1 S2 C3 N3 178.1(3) ?
N1 S2 C3 C9 0.0(3) ?
C9 C4 C5 C6 0.7(5) ?
C9 C4 C5 N2 -178.7(3) ?
C4 C5 C6 C7 -2.8(5) ?
N2 C5 C6 C7 176.6(3) ?
C5 C6 C7 C8 2.8(5) ?
S2 N1 C8 C9 0.0(4) ?
S2 N1 C8 C7 178.9(3) ?
C6 C7 C8 N1 -179.8(4) ?
C6 C7 C8 C9 -0.9(5) ?
N3 C3 C9 C4 4.2(5) ?
S2 C3 C9 C4 -177.6(3) ?
N3 C3 C9 C8 -178.2(3) ?
S2 C3 C9 C8 0.0(3) ?
C5 C4 C9 C3 178.6(3) ?
C5 C4 C9 C8 1.2(5) ?
N1 C8 C9 C3 -0.1(4) ?
C7 C8 C9 C3 -179.0(3) ?
N1 C8 C9 C4 177.8(3) ?
C7 C8 C9 C4 -1.2(5) ?
C4 C5 N2 O2 -169.3(3) ?
C6 C5 N2 O2 11.3(5) ?
C4 C5 N2 O1 10.0(5) yes
C6 C5 N2 O1 -169.5(3) ?
C9 C3 N3 N4 -177.8(3) ?
S2 C3 N3 N4 4.3(4) yes
C3 N3 N4 N5 179.7(2) yes
N3 N4 N5 C10 -179.9(3) yes
N3 N4 N5 C16 0.1(4) yes
N4 N5 C10 C15 167.1(3) ?
C16 N5 C10 C15 -12.9(5) ?
N4 N5 C10 C11 -10.8(5) yes
C16 N5 C10 C11 169.3(3) ?
C15 C10 C11 C12 -0.8(5) ?
N5 C10 C11 C12 177.0(3) ?
C10 C11 C12 C13 0.4(6) ?
C11 C12 C13 C14 0.7(6) ?
C12 C13 C14 C15 -1.4(7) ?
C11 C10 C15 C14 0.2(6) ?
N5 C10 C15 C14 -177.7(3) ?
C13 C14 C15 C10 0.9(6) ?
N4 N5 C16 C17 85.5(4) yes
C10 N5 C16 C17 -94.6(4) ?
N5 C16 C17 C18 172.3(5) yes
N5 C16 C17 C18' -163.2(8) yes
C16 C17 C18 C19 80.5(13) yes
C18' C17 C18 C19 10.9(17) ?
C16 C17 C18' C19' -179.1(13) yes
C18 C17 C18' C19' -60.0(19) ?
