#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:17:09 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180070 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/16/7051699.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_7051699
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         'C13 H15 N5 S'
_chemical_formula_sum            'C13 H15 N5 S'
_chemical_formula_weight         273.36
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.354(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.1254(10)
_cell_length_b                   14.916(2)
_cell_length_c                   15.9171(19)
_cell_measurement_reflns_used    102
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      19.8
_cell_measurement_theta_min      4.5
_cell_volume                     2732.4(6)
_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  'WinGX publication routines (Farrugia, 1999)'
_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 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0807
_diffrn_reflns_av_sigmaI/netI    0.1854
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18467
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.687
_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    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepipped
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         7840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.911
_refine_ls_R_factor_all          0.2126
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0665P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1632
_reflns_number_gt                2881
_reflns_number_total             7840
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b902225b.txt
_cod_data_source_block           oo39
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7051699
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 0.55160(6) -0.14138(7) 0.25201(5) 0.0512(3) Uani 1 1 d . . .
N1 N 0.24317(16) -0.01414(15) 0.19844(15) 0.0346(6) Uani 1 1 d . . .
H1A H 0.2412 -0.0013 0.2504 0.042 Uiso 1 1 d R . .
N2 N 0.36697(17) -0.03373(17) 0.22587(15) 0.0367(6) Uani 1 1 d . . .
N3 N 0.33839(18) -0.18384(17) 0.25362(16) 0.0378(6) Uani 1 1 d . . .
N4 N 0.21433(16) -0.17159(16) 0.23088(16) 0.0352(6) Uani 1 1 d . . .
H4A H 0.2021 -0.1500 0.2779 0.042 Uiso 1 1 d R . .
N5 N 0.06390(19) -0.04843(16) 0.29107(17) 0.0393(6) Uani 1 1 d . . .
C1 C 0.4096(2) -0.1182(2) 0.24304(18) 0.0362(8) Uani 1 1 d . . .
C2 C 0.1801(2) -0.09811(19) 0.16637(19) 0.0329(7) Uani 1 1 d . . .
H2 H 0.2136 -0.1209 0.1217 0.039 Uiso 1 1 d R . .
C3 C 0.0491(2) -0.08272(19) 0.13934(19) 0.0337(7) Uani 1 1 d . . .
C4 C -0.0180(2) -0.0939(2) 0.0526(2) 0.0441(8) Uani 1 1 d . . .
H4 H 0.0181 -0.1078 0.0106 0.053 Uiso 1 1 calc R . .
C5 C -0.1402(3) -0.0848(2) 0.0253(2) 0.0560(9) Uani 1 1 d . . .
H5 H -0.1834 -0.0921 -0.0340 0.067 Uiso 1 1 calc R . .
C6 C -0.1949(2) -0.0654(2) 0.0862(3) 0.0570(10) Uani 1 1 d . . .
H6 H -0.2755 -0.0614 0.0685 0.068 Uiso 1 1 calc R . .
C7 C -0.1294(2) -0.0512(2) 0.1765(2) 0.0417(8) Uani 1 1 d . . .
C8 C -0.1791(3) -0.0292(2) 0.2440(3) 0.0604(11) Uani 1 1 d . . .
H8 H -0.2591 -0.0222 0.2296 0.072 Uiso 1 1 calc R . .
C9 C -0.1108(3) -0.0184(2) 0.3287(3) 0.0636(11) Uani 1 1 d . . .
H9 H -0.1436 -0.0044 0.3726 0.076 Uiso 1 1 calc R . .
C10 C 0.0113(3) -0.0288(2) 0.3501(2) 0.0507(9) Uani 1 1 d . . .
H10 H 0.0568 -0.0214 0.4088 0.061 Uiso 1 1 calc R . .
C11 C -0.0055(2) -0.05997(19) 0.2030(2) 0.0357(7) Uani 1 1 d . . .
C12 C 0.4343(2) 0.0417(2) 0.2087(2) 0.0493(9) Uani 1 1 d . . .
H12A H 0.5123 0.0389 0.2488 0.074 Uiso 1 1 calc R . .
H12B H 0.3989 0.0970 0.2173 0.074 Uiso 1 1 calc R . .
H12C H 0.4359 0.0385 0.1489 0.074 Uiso 1 1 calc R . .
C13 C 0.3696(3) -0.2788(2) 0.2621(2) 0.0534(9) Uani 1 1 d . . .
H13A H 0.3613 -0.3032 0.2046 0.080 Uiso 1 1 calc R . .
H13B H 0.3193 -0.3103 0.2880 0.080 Uiso 1 1 calc R . .
H13C H 0.4487 -0.2853 0.2993 0.080 Uiso 1 1 calc R . .
S2 S 0.78308(6) 0.22942(7) 0.52634(6) 0.0553(3) Uani 1 1 d . . .
N6 N 0.45829(17) 0.12755(16) 0.43325(16) 0.0356(6) Uani 1 1 d . . .
H6A H 0.4398 0.1476 0.3789 0.043 Uiso 1 1 d R . .
N7 N 0.58289(17) 0.14002(17) 0.46018(16) 0.0381(6) Uani 1 1 d . . .
N8 N 0.56572(18) 0.29207(17) 0.48645(16) 0.0374(6) Uani 1 1 d . . .
N9 N 0.44076(16) 0.28664(16) 0.46383(15) 0.0353(6) Uani 1 1 d . . .
H9A H 0.4140 0.2984 0.4067 0.042 Uiso 1 1 d R . .
N10 N 0.25750(17) 0.20506(16) 0.29928(15) 0.0342(6) Uani 1 1 d . . .
C14 C 0.6344(2) 0.2199(2) 0.48824(18) 0.0350(7) Uani 1 1 d . . .
C15 C 0.4090(2) 0.1947(2) 0.47989(18) 0.0322(7) Uani 1 1 d . . .
H15 H 0.4513 0.1795 0.5409 0.039 Uiso 1 1 d R . .
C16 C 0.2771(2) 0.18610(19) 0.45429(18) 0.0292(7) Uani 1 1 d . . .
C17 C 0.2255(2) 0.17257(19) 0.51868(18) 0.0343(7) Uani 1 1 d . . .
H17 H 0.2720 0.1639 0.5769 0.041 Uiso 1 1 calc R . .
C18 C 0.1025(2) 0.1716(2) 0.4983(2) 0.0400(8) Uani 1 1 d . . .
H18 H 0.0700 0.1634 0.5435 0.048 Uiso 1 1 calc R . .
C19 C 0.0315(2) 0.1826(2) 0.41301(19) 0.0356(7) Uani 1 1 d . . .
H19 H -0.0488 0.1834 0.4007 0.043 Uiso 1 1 calc R . .
C20 C 0.0804(2) 0.19287(18) 0.34277(18) 0.0282(6) Uani 1 1 d . . .
C21 C 0.0138(2) 0.2001(2) 0.25265(19) 0.0359(7) Uani 1 1 d . . .
H21 H -0.0669 0.1994 0.2364 0.043 Uiso 1 1 calc R . .
C22 C 0.0671(2) 0.2083(2) 0.18920(19) 0.0416(8) Uani 1 1 d . . .
H22 H 0.0238 0.2117 0.1296 0.050 Uiso 1 1 calc R . .
C23 C 0.1893(2) 0.2114(2) 0.21651(19) 0.0400(8) Uani 1 1 d . . .
H23 H 0.2247 0.2184 0.1729 0.048 Uiso 1 1 calc R . .
C24 C 0.2048(2) 0.19519(18) 0.36414(17) 0.0269(6) Uani 1 1 d . . .
C25 C 0.6457(3) 0.0544(2) 0.4712(3) 0.0613(10) Uani 1 1 d . . .
H25A H 0.7165 0.0624 0.4572 0.092 Uiso 1 1 calc R . .
H25B H 0.5982 0.0105 0.4323 0.092 Uiso 1 1 calc R . .
H25C H 0.6636 0.0346 0.5314 0.092 Uiso 1 1 calc R . .
C26 C 0.6093(3) 0.3828(2) 0.5101(2) 0.0466(8) Uani 1 1 d . . .
H26A H 0.6925 0.3827 0.5263 0.070 Uiso 1 1 calc R . .
H26B H 0.5861 0.4035 0.5591 0.070 Uiso 1 1 calc R . .
H26C H 0.5778 0.4218 0.4603 0.070 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 107.9(2) . . ?
N2 N1 H1A 95.4 . . ?
C2 N1 H1A 110.9 . . ?
C1 N2 N1 122.6(2) . . ?
C1 N2 C12 123.4(2) . . ?
N1 N2 C12 111.9(2) . . ?
C1 N3 N4 122.3(2) . . ?
C1 N3 C13 123.9(2) . . ?
N4 N3 C13 111.4(2) . . ?
N3 N4 C2 108.18(19) . . ?
N3 N4 H4A 106.1 . . ?
C2 N4 H4A 103.8 . . ?
C10 N5 C11 117.7(2) . . ?
N3 C1 N2 118.7(2) . . ?
N3 C1 S1 120.5(2) . . ?
N2 C1 S1 120.8(2) . . ?
N4 C2 N1 113.0(2) . . ?
N4 C2 C3 110.4(2) . . ?
N1 C2 C3 110.5(2) . . ?
N4 C2 H2 99.1 . . ?
N1 C2 H2 104.9 . . ?
C3 C2 H2 118.5 . . ?
C4 C3 C11 119.1(2) . . ?
C4 C3 C2 119.9(3) . . ?
C11 C3 C2 120.9(3) . . ?
C3 C4 C5 121.9(3) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 120.5(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C8 124.2(3) . . ?
C6 C7 C11 119.0(3) . . ?
C8 C7 C11 116.9(3) . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 119.4(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
N5 C10 C9 123.5(3) . . ?
N5 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
N5 C11 C3 118.5(2) . . ?
N5 C11 C7 121.9(3) . . ?
C3 C11 C7 119.7(3) . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N7 N6 C15 108.3(2) . . ?
N7 N6 H6A 99.6 . . ?
C15 N6 H6A 104.2 . . ?
C14 N7 N6 122.8(2) . . ?
C14 N7 C25 123.8(2) . . ?
N6 N7 C25 112.2(2) . . ?
C14 N8 N9 123.4(2) . . ?
C14 N8 C26 124.1(2) . . ?
N9 N8 C26 112.5(2) . . ?
N8 N9 C15 108.70(19) . . ?
N8 N9 H9A 105.2 . . ?
C15 N9 H9A 109.5 . . ?
C23 N10 C24 117.4(2) . . ?
N7 C14 N8 118.3(2) . . ?
N7 C14 S2 120.9(2) . . ?
N8 C14 S2 120.8(2) . . ?
N9 C15 N6 112.0(2) . . ?
N9 C15 C16 110.0(2) . . ?
N6 C15 C16 111.4(2) . . ?
N9 C15 H15 107.9 . . ?
N6 C15 H15 100.0 . . ?
C16 C15 H15 115.3 . . ?
C17 C16 C24 118.8(2) . . ?
C17 C16 C15 119.9(2) . . ?
C24 C16 C15 121.2(2) . . ?
C16 C17 C18 121.5(3) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C19 C18 C17 120.7(2) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 120.1(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 123.9(2) . . ?
C21 C20 C24 117.4(2) . . ?
C19 C20 C24 118.7(3) . . ?
C22 C21 C20 120.4(2) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 118.2(3) . . ?
C21 C22 H22 120.9 . . ?
C23 C22 H22 120.9 . . ?
N10 C23 C22 125.0(3) . . ?
N10 C23 H23 117.5 . . ?
C22 C23 H23 117.5 . . ?
N10 C24 C16 118.5(2) . . ?
N10 C24 C20 121.5(2) . . ?
C16 C24 C20 120.0(2) . . ?
N7 C25 H25A 109.5 . . ?
N7 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N7 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N8 C26 H26A 109.5 . . ?
N8 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N8 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
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 1.717(3) . ?
N1 N2 1.455(3) . ?
N1 C2 1.473(3) . ?
N1 H1A 0.8568 . ?
N2 C1 1.357(4) . ?
N2 C12 1.465(4) . ?
N3 C1 1.351(4) . ?
N3 N4 1.444(3) . ?
N3 C13 1.462(4) . ?
N4 C2 1.470(3) . ?
N4 H4A 0.8695 . ?
N5 C10 1.324(3) . ?
N5 C11 1.400(4) . ?
C2 C3 1.527(3) . ?
C2 H2 0.9837 . ?
C3 C4 1.375(4) . ?
C3 C11 1.416(4) . ?
C4 C5 1.414(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.423(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.425(5) . ?
C7 C11 1.432(4) . ?
C8 C9 1.352(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.419(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
S2 C14 1.717(3) . ?
N6 N7 1.447(3) . ?
N6 C15 1.480(3) . ?
N6 H6A 0.8748 . ?
N7 C14 1.354(4) . ?
N7 C25 1.469(4) . ?
N8 C14 1.356(4) . ?
N8 N9 1.445(3) . ?
N8 C26 1.458(4) . ?
N9 C15 1.469(3) . ?
N9 H9A 0.8820 . ?
N10 C23 1.320(3) . ?
N10 C24 1.383(3) . ?
C15 C16 1.527(3) . ?
C15 H15 0.9715 . ?
C16 C17 1.373(4) . ?
C16 C24 1.433(3) . ?
C17 C18 1.423(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.370(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.430(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.411(4) . ?
C20 C24 1.438(3) . ?
C21 C22 1.365(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.407(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
