#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/43/2224361.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_2224361
loop_
_publ_author_name
'Carvalho, Samir A.'
'de Feitosa, Larisse O.'
'da Silva, Edson F.'
'Tiekink, Edward R. T.'
'Wardell, James L.'
'Wardell, Solange M. S. V.'
_publ_section_title
;
 5-(3-Nitrobenzyl)-1,3,4-thiadiazol-2-amine
;
_journal_coeditor_code           LH2958
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3200
_journal_page_last               o3201
_journal_paper_doi               10.1107/S1600536809049654
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C9 H8 N4 O2 S'
_chemical_formula_moiety         'C9 H8 N4 O2 S'
_chemical_formula_sum            'C9 H8 N4 O2 S'
_chemical_formula_weight         236.26
_chemical_name_systematic
;
5-(3-Nitrobenzyl)-1,3,4-thiadiazol-2-amine
;
_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                80.980(3)
_cell_angle_beta                 85.677(3)
_cell_angle_gamma                79.855(3)
_cell_formula_units_Z            2
_cell_length_a                   5.0878(2)
_cell_length_b                   5.6213(3)
_cell_length_c                   17.8035(9)
_cell_measurement_reflns_used    11753
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     494.42(4)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  '10 cm confocal mirrors'
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_av_sigmaI/netI    0.033
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9074
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.5
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.33
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2256
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.042
_refine_ls_R_factor_gt           0.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0347P)²+0.3167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.081
_refine_ls_wR_factor_ref         0.086
_reflns_number_gt                1973
_reflns_number_total             2256
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2958.cif
_cod_data_source_block           I
_cod_database_code               2224361
_cod_database_fobs_code          2224361
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 0.39352(8) 0.87897(7) 0.63466(2) 0.01803(12) Uani d . 1 . .
O O1 -0.3420(3) 0.5966(2) 0.79836(7) 0.0282(3) Uani d . 1 . .
O O2 -0.2766(3) 0.4981(2) 0.91883(7) 0.0326(3) Uani d . 1 . .
N N1 0.7365(3) 1.1393(2) 0.56903(8) 0.0187(3) Uani d . 1 . .
N N2 0.5591(3) 1.2890(2) 0.61221(8) 0.0185(3) Uani d . 1 . .
N N3 0.8153(3) 0.7356(2) 0.54139(8) 0.0198(3) Uani d D 1 . .
H H1N 0.7552 0.5959 0.5485 0.030 Uiso d D 1 . .
H H2N 0.9445 0.7652 0.5073 0.030 Uiso d D 1 . .
N N4 -0.2396(3) 0.6204(2) 0.85639(8) 0.0218(3) Uani d . 1 . .
C C1 0.6754(3) 0.9177(3) 0.57569(9) 0.0160(3) Uani d . 1 . .
C C2 0.3731(3) 1.1810(3) 0.64921(9) 0.0161(3) Uani d . 1 . .
C C3 0.1583(3) 1.2978(3) 0.70123(9) 0.0189(3) Uani d . 1 . .
H H3A -0.0131 1.3369 0.6754 0.023 Uiso calc R 1 . .
H H3B 0.2049 1.4528 0.7116 0.023 Uiso calc R 1 . .
C C4 0.1235(3) 1.1329(3) 0.77600(9) 0.0167(3) Uani d . 1 . .
C C5 -0.0430(3) 0.9582(3) 0.78225(9) 0.0164(3) Uani d . 1 . .
H H5 -0.1411 0.9442 0.7403 0.020 Uiso calc R 1 . .
C C6 -0.0634(3) 0.8046(3) 0.85083(9) 0.0180(3) Uani d . 1 . .
C C7 0.0726(3) 0.8188(3) 0.91408(10) 0.0231(4) Uani d . 1 . .
H H7 0.0545 0.7117 0.9604 0.028 Uiso calc R 1 . .
C C8 0.2360(3) 0.9947(3) 0.90746(10) 0.0249(4) Uani d . 1 . .
H H8 0.3309 1.0096 0.9500 0.030 Uiso calc R 1 . .
C C9 0.2626(3) 1.1498(3) 0.83935(10) 0.0208(3) Uani d . 1 . .
H H9 0.3766 1.2684 0.8358 0.025 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 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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
C1 S1 C2 . . 87.36(7) ?
C1 N1 N2 . . 111.82(13) ?
C2 N2 N1 . . 113.45(12) ?
C1 N3 H1N . . 117.3 ?
C1 N3 H2N . . 119.9 ?
H1N N3 H2N . . 122.0 ?
O1 N4 O2 . . 123.37(14) ?
O1 N4 C6 . . 118.11(13) ?
O2 N4 C6 . . 118.52(14) ?
N1 C1 N3 . . 124.39(14) ?
N1 C1 S1 . . 113.68(12) ?
N3 C1 S1 . . 121.93(11) ?
N2 C2 C3 . . 124.72(13) ?
N2 C2 S1 . . 113.68(12) ?
C3 C2 S1 . . 121.59(11) ?
C2 C3 C4 . . 112.03(13) ?
C2 C3 H3A . . 109.2 ?
C4 C3 H3A . . 109.2 ?
C2 C3 H3B . . 109.2 ?
C4 C3 H3B . . 109.2 ?
H3A C3 H3B . . 107.9 ?
C5 C4 C9 . . 118.89(15) ?
C5 C4 C3 . . 120.45(14) ?
C9 C4 C3 . . 120.64(14) ?
C6 C5 C4 . . 118.95(14) ?
C6 C5 H5 . . 120.5 ?
C4 C5 H5 . . 120.5 ?
C7 C6 C5 . . 122.94(15) ?
C7 C6 N4 . . 118.81(14) ?
C5 C6 N4 . . 118.25(14) ?
C6 C7 C8 . . 117.65(15) ?
C6 C7 H7 . . 121.2 ?
C8 C7 H7 . . 121.2 ?
C9 C8 C7 . . 120.82(15) ?
C9 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C8 C9 C4 . . 120.74(15) ?
C8 C9 H9 . . 119.6 ?
C4 C9 H9 . . 119.6 ?
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 C1 . 1.7373(16) ?
S1 C2 . 1.7412(15) ?
O1 N4 . 1.2271(19) ?
O2 N4 . 1.2321(18) ?
N1 C1 . 1.321(2) ?
N1 N2 . 1.3949(19) ?
N2 C2 . 1.297(2) ?
N3 C1 . 1.342(2) ?
N3 H1N . 0.8800 ?
N3 H2N . 0.8799 ?
N4 C6 . 1.472(2) ?
C2 C3 . 1.506(2) ?
C3 C4 . 1.516(2) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C5 . 1.393(2) ?
C4 C9 . 1.400(2) ?
C5 C6 . 1.389(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.385(2) ?
C7 C8 . 1.386(2) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.391(2) ?
C8 H8 . 0.9500 ?
C9 H9 . 0.9500 ?
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
N3 H1n N2 1_545 0.88 2.25 3.0828(19) 157
N3 H2n N1 2_776 0.88 2.12 3.003(2) 175
C3 H3a N2 1_455 0.99 2.60 3.552(2) 162
C3 H3b S1 1_565 0.99 2.85 3.6687(17) 141
C7 H7 O2 2_567 0.95 2.53 3.355(2) 145
C9 H9 O1 1_665 0.95 2.51 3.446(2) 168
C5 H5 Cg 1_455 0.95 2.86 3.7708(17) 160
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
C1 N1 N2 C2 . . . . -0.19(19) ?
N2 N1 C1 N3 . . . . -178.79(14) ?
N2 N1 C1 S1 . . . . 0.65(17) ?
C2 S1 C1 N1 . . . . -0.70(12) ?
C2 S1 C1 N3 . . . . 178.76(14) ?
N1 N2 C2 C3 . . . . 178.85(14) ?
N1 N2 C2 S1 . . . . -0.36(17) ?
C1 S1 C2 N2 . . . . 0.59(12) ?
C1 S1 C2 C3 . . . . -178.64(14) ?
N2 C2 C3 C4 . . . . -133.70(16) ?
S1 C2 C3 C4 . . . . 45.44(18) ?
C2 C3 C4 C5 . . . . -85.79(18) ?
C2 C3 C4 C9 . . . . 92.73(17) ?
C9 C4 C5 C6 . . . . -0.7(2) ?
C3 C4 C5 C6 . . . . 177.85(14) ?
C4 C5 C6 C7 . . . . 0.8(2) ?
C4 C5 C6 N4 . . . . -179.81(13) ?
O1 N4 C6 C7 . . . . -174.26(14) ?
O2 N4 C6 C7 . . . . 5.7(2) ?
O1 N4 C6 C5 . . . . 6.3(2) ?
O2 N4 C6 C5 . . . . -173.78(14) ?
C5 C6 C7 C8 . . . . -0.2(2) ?
N4 C6 C7 C8 . . . . -179.63(15) ?
C6 C7 C8 C9 . . . . -0.4(3) ?
C7 C8 C9 C4 . . . . 0.5(3) ?
C5 C4 C9 C8 . . . . 0.1(2) ?
C3 C4 C9 C8 . . . . -178.44(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743946
