#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/16/7051696.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_7051696
loop_
_publ_author_name
'Oms, Olivier'
'Norel, Lucie'
'Chamoreau, Lise-Marie'
'Rousselière, Hélène'
'Train, Cyrille'
_publ_section_title
;
 Conformation and crystal packing sensitivity to substitution of
 thioxo- and oxo-tetrazane derivatives
;
_journal_issue                   8
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1663
_journal_paper_doi               10.1039/b902225b
_journal_volume                  33
_journal_year                    2009
_chemical_formula_moiety         'C9 H13 N5 S1'
_chemical_formula_sum            'C9 H13 N5 S'
_chemical_formula_weight         223.30
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 118.320(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9056(17)
_cell_length_b                   9.6629(7)
_cell_length_c                   11.3482(19)
_cell_measurement_reflns_used    143
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      22
_cell_measurement_theta_min      3
_cell_volume                     1149.3(3)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16000
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         2.87
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
R.H. Blessing, Acta Cryst.(1995), A51, 33-38
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         3352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0621
_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)+(0.1132P)²+0.1742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1841
_refine_ls_wR_factor_ref         0.2046
_reflns_number_gt                2162
_reflns_number_total             3352
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b902225b.txt
_cod_data_source_block           new
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7051696
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.16927(6) 0.55347(7) 1.25406(6) 0.0485(2) Uani 1 1 d . . .
N1 N 0.80091(18) 0.6291(2) 0.99905(19) 0.0434(5) Uani 1 1 d . . .
H1N H 0.7882 0.5871 0.9242 0.052 Uiso 1 1 d R . .
N2 N 0.9173(2) 0.5748(2) 1.1038(2) 0.0444(5) Uani 1 1 d . . .
N3 N 1.03835(17) 0.7288(2) 1.0526(2) 0.0413(5) Uani 1 1 d . . .
N4 N 0.92666(18) 0.8005(2) 0.9557(2) 0.0467(5) Uani 1 1 d . . .
H4N H 0.9028 0.7565 0.8791 0.056 Uiso 1 1 d R . .
N5 N 0.6742(2) 0.7913(3) 0.7411(2) 0.0575(6) Uani 1 1 d . . .
C1 C 1.0337(2) 0.6237(2) 1.1291(2) 0.0367(5) Uani 1 1 d . . .
C2 C 0.8201(2) 0.7739(2) 0.9797(2) 0.0408(5) Uani 1 1 d . . .
H2 H 0.8390 0.8207 1.0696 0.049 Uiso 1 1 d R . .
C3 C 0.6984(2) 0.8306(2) 0.8637(2) 0.0384(5) Uani 1 1 d . . .
C4 C 0.6200(3) 0.9163(3) 0.8880(3) 0.0590(7) Uani 1 1 d . . .
H4 H 0.6395 0.9414 0.9748 0.071 Uiso 1 1 calc R . .
C5 C 0.5082(3) 0.9652(4) 0.7763(4) 0.0779(10) Uani 1 1 d . . .
H5 H 0.4532 1.0253 0.7879 0.093 Uiso 1 1 calc R . .
C6 C 0.4825(3) 0.9233(3) 0.6521(3) 0.0653(8) Uani 1 1 d . . .
H6 H 0.4085 0.9524 0.5775 0.078 Uiso 1 1 calc R . .
C8 C 1.1568(2) 0.7937(3) 1.0717(3) 0.0454(6) Uani 1 1 d . . .
H8A H 1.1374 0.8655 1.0064 0.068 Uiso 1 1 calc R . .
H8B H 1.2100 0.7254 1.0612 0.068 Uiso 1 1 calc R . .
H8C H 1.2008 0.8328 1.1599 0.068 Uiso 1 1 calc R . .
C9 C 0.8992(3) 0.4729(2) 1.1900(2) 0.0476(6) Uani 1 1 d . . .
H9A H 0.8099 0.4526 1.1538 0.071 Uiso 1 1 calc R . .
H9B H 0.9312 0.5102 1.2785 0.071 Uiso 1 1 calc R . .
H9C H 0.9446 0.3895 1.1938 0.071 Uiso 1 1 calc R . .
C7 C 0.5663(3) 0.8379(4) 0.6377(3) 0.0689(9) Uani 1 1 d . . .
H7 H 0.5477 0.8105 0.5518 0.083 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C2 108.62(17) . . ?
N2 N1 H1N 106.6 . . ?
C2 N1 H1N 105.3 . . ?
C1 N2 N1 122.46(18) . . ?
C1 N2 C9 123.2(2) . . ?
N1 N2 C9 114.01(19) . . ?
C1 N3 N4 123.15(18) . . ?
C1 N3 C8 123.83(19) . . ?
N4 N3 C8 112.53(18) . . ?
N3 N4 C2 110.31(17) . . ?
N3 N4 H4N 105.6 . . ?
C2 N4 H4N 101.5 . . ?
C3 N5 C7 117.4(2) . . ?
N3 C1 N2 118.2(2) . . ?
N3 C1 S1 121.41(18) . . ?
N2 C1 S1 120.37(16) . . ?
N4 C2 N1 114.63(19) . . ?
N4 C2 C3 109.54(18) . . ?
N1 C2 C3 108.88(18) . . ?
N4 C2 H2 107.9 . . ?
N1 C2 H2 104.3 . . ?
C3 C2 H2 111.5 . . ?
N5 C3 C4 123.4(2) . . ?
N5 C3 C2 116.4(2) . . ?
C4 C3 C2 120.2(2) . . ?
C3 C4 C5 117.5(3) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C7 119.3(3) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N5 C7 C6 123.3(3) . . ?
N5 C7 H7 118.4 . . ?
C6 C7 H7 118.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.705(2) . ?
N1 N2 1.431(3) . ?
N1 C2 1.451(3) . ?
N1 H1N 0.8871 . ?
N2 C1 1.359(3) . ?
N2 C9 1.475(3) . ?
N3 C1 1.354(3) . ?
N3 N4 1.439(3) . ?
N3 C8 1.463(3) . ?
N4 C2 1.441(3) . ?
N4 H4N 0.8857 . ?
N5 C3 1.334(3) . ?
N5 C7 1.342(4) . ?
C2 C3 1.525(3) . ?
C2 H2 1.0385 . ?
C3 C4 1.371(4) . ?
C4 C5 1.414(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.354(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.363(5) . ?
C6 H6 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C7 H7 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652897
