#------------------------------------------------------------------------------
#$Date: 2016-03-05 11:02:08 +0200 (Sat, 05 Mar 2016) $
#$Revision: 177742 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/41/7224175.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_7224175
loop_
_publ_author_name
'Taouss, Christina'
'Döring, Cindy'
'Jones, Peter G.'
'Pinkert, Lukas'
'Strey, Mark'
_publ_section_title
;
 Single crystals that spontaneously spawn other single crystals: a ternary
 and a binary adduct of thiourea and 2,5-dimethylpyrazine
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              1842
_journal_paper_doi               10.1039/C6CE00100A
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C8 H16 N4 O S'
_chemical_formula_weight         216.31
_chemical_name_systematic
;
 ?
;
_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
_audit_update_record
;
2016-01-04 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                103.892(3)
_cell_angle_beta                 97.021(3)
_cell_angle_gamma                90.970(3)
_cell_formula_units_Z            4
_cell_length_a                   8.3895(3)
_cell_length_b                   9.1961(3)
_cell_length_c                   15.9849(6)
_cell_measurement_reflns_used    29708
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      76.0260
_cell_measurement_theta_min      4.9560
_cell_volume                     1186.83(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean 10.3543
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Atlas, Nova'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            49484
_diffrn_reflns_theta_full        75.00
_diffrn_reflns_theta_max         76.26
_diffrn_reflns_theta_min         4.96
_diffrn_source                   'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.257
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0051(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4970
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0631P)²+0.1887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.0987
_reflns_number_gt                4538
_reflns_number_total             4970
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce00100a2.cif
_cod_data_source_block           hanosol
_cod_depositor_comments
'Adding full bibliography for 7224174--7224176.cif.'
_cod_original_cell_volume        1186.83(8)
_cod_database_code               7224175
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.76421(3) 0.30011(3) 0.24593(2) 0.03404(11) Uani 1 1 d .
N1 N 0.92457(13) 0.55905(12) 0.31626(8) 0.0328(2) Uani 1 1 d .
H01 H 0.936(2) 0.652(2) 0.3450(12) 0.053(5) Uiso 1 1 d .
H02 H 1.010(2) 0.508(2) 0.2992(11) 0.040(4) Uiso 1 1 d .
C2 C 0.78358(14) 0.48445(13) 0.30120(8) 0.0274(2) Uani 1 1 d .
N3 N 0.65644(14) 0.55593(13) 0.33032(8) 0.0367(3) Uani 1 1 d .
H04 H 0.560(2) 0.509(2) 0.3145(11) 0.045(5) Uiso 1 1 d .
H03 H 0.665(2) 0.651(2) 0.3635(13) 0.057(5) Uiso 1 1 d .
S2 S 0.27459(3) 0.40444(3) 0.27225(2) 0.03523(11) Uani 1 1 d .
N4 N 0.39640(14) 0.13694(13) 0.23108(10) 0.0427(3) Uani 1 1 d .
H05 H 0.390(2) 0.038(2) 0.2113(12) 0.051(5) Uiso 1 1 d .
H06 H 0.496(2) 0.189(2) 0.2404(11) 0.047(5) Uiso 1 1 d .
C5 C 0.26421(15) 0.21355(13) 0.24187(8) 0.0287(2) Uani 1 1 d .
N6 N 0.12378(13) 0.13681(13) 0.22831(7) 0.0326(2) Uani 1 1 d .
H08 H 0.036(2) 0.185(2) 0.2354(11) 0.047(5) Uiso 1 1 d .
H07 H 0.114(2) 0.040(2) 0.2107(10) 0.037(4) Uiso 1 1 d .
N11 N -0.04130(15) -0.38709(13) 0.06729(7) 0.0379(3) Uani 1 1 d .
C12 C -0.00465(18) -0.35640(15) -0.00594(9) 0.0369(3) Uani 1 1 d .
C13 C -0.03609(19) -0.52920(16) 0.07276(9) 0.0388(3) Uani 1 1 d .
H13 H -0.0612 -0.5532 0.1244 0.047 Uiso 1 1 calc R
C14 C -0.0104(3) -0.19718(18) -0.01320(11) 0.0589(5) Uani 1 1 d .
H14A H -0.0759 -0.1411 0.0292 0.088 Uiso 0.50 1 calc PR
H14B H -0.0579 -0.1949 -0.0720 0.088 Uiso 0.50 1 calc PR
H14C H 0.0989 -0.1514 -0.0016 0.088 Uiso 0.50 1 calc PR
H14D H 0.0526 -0.1838 -0.0588 0.088 Uiso 0.50 1 calc PR
H14E H 0.0346 -0.1300 0.0424 0.088 Uiso 0.50 1 calc PR
H14F H -0.1222 -0.1735 -0.0280 0.088 Uiso 0.50 1 calc PR
N21 N 0.42689(16) -0.39411(13) 0.05828(8) 0.0407(3) Uani 1 1 d .
C22 C 0.48466(18) -0.35868(15) -0.00893(9) 0.0384(3) Uani 1 1 d .
C23 C 0.44287(19) -0.53370(17) 0.06702(9) 0.0419(3) Uani 1 1 d .
H23 H 0.4033 -0.5606 0.1147 0.050 Uiso 1 1 calc R
C24 C 0.4678(3) -0.20180(18) -0.01971(11) 0.0569(4) Uani 1 1 d .
H24A H 0.3888 -0.1518 0.0164 0.085 Uiso 0.50 1 calc PR
H24B H 0.4316 -0.2050 -0.0808 0.085 Uiso 0.50 1 calc PR
H24C H 0.5719 -0.1462 -0.0018 0.085 Uiso 0.50 1 calc PR
H24D H 0.5394 -0.1835 -0.0605 0.085 Uiso 0.50 1 calc PR
H24E H 0.4966 -0.1303 0.0367 0.085 Uiso 0.50 1 calc PR
H24F H 0.3563 -0.1891 -0.0423 0.085 Uiso 0.50 1 calc PR
N31 N 0.56576(14) 0.87451(13) 0.45026(8) 0.0393(3) Uani 1 1 d .
C32 C 0.46856(16) 0.85985(16) 0.50866(9) 0.0363(3) Uani 1 1 d .
C33 C 0.59479(17) 1.01334(16) 0.44259(9) 0.0394(3) Uani 1 1 d .
H33 H 0.6628 1.0265 0.4014 0.047 Uiso 1 1 calc R
C34 C 0.4313(2) 0.70583(18) 0.51952(12) 0.0539(4) Uani 1 1 d .
H34A H 0.3784 0.6430 0.4643 0.081 Uiso 1 1 calc R
H34B H 0.3598 0.7126 0.5643 0.081 Uiso 1 1 calc R
H34C H 0.5314 0.6613 0.5370 0.081 Uiso 1 1 calc R
N41 N 0.97937(14) 0.86524(12) 0.43669(7) 0.0327(2) Uani 1 1 d .
C42 C 0.97102(16) 0.86803(14) 0.52021(8) 0.0311(3) Uani 1 1 d .
C43 C 1.00806(16) 0.99586(14) 0.41742(8) 0.0325(3) Uani 1 1 d .
H43 H 1.0145 0.9960 0.3585 0.039 Uiso 1 1 calc R
C44 C 0.9386(2) 0.72262(16) 0.54356(10) 0.0441(3) Uani 1 1 d .
H44A H 0.9501 0.6388 0.4939 0.066 Uiso 0.50 1 calc PR
H44B H 0.8289 0.7192 0.5585 0.066 Uiso 0.50 1 calc PR
H44C H 1.0154 0.7149 0.5935 0.066 Uiso 0.50 1 calc PR
H44D H 0.9129 0.7431 0.6033 0.066 Uiso 0.50 1 calc PR
H44E H 1.0341 0.6628 0.5388 0.066 Uiso 0.50 1 calc PR
H44F H 0.8475 0.6670 0.5038 0.066 Uiso 0.50 1 calc PR
O1 O -0.08637(13) -0.13722(12) 0.20434(7) 0.0474(3) Uani 1 1 d .
H09 H -0.067(3) -0.210(3) 0.1640(14) 0.068(6) Uiso 1 1 d .
C10 C -0.2513(2) -0.1303(2) 0.20604(13) 0.0596(4) Uani 1 1 d .
H10A H -0.2731 -0.0481 0.2544 0.089 Uiso 1 1 calc R
H10B H -0.2945 -0.2253 0.2137 0.089 Uiso 1 1 calc R
H10C H -0.3028 -0.1125 0.1512 0.089 Uiso 1 1 calc R
O2 O 0.29835(13) -0.16937(11) 0.18184(7) 0.0426(2) Uani 1 1 d .
H10 H 0.334(3) -0.241(3) 0.1459(14) 0.064(6) Uiso 1 1 d .
C20 C 0.2892(2) -0.22107(18) 0.25761(11) 0.0486(4) Uani 1 1 d .
H20A H 0.3897 -0.2673 0.2725 0.073 Uiso 1 1 calc R
H20B H 0.1993 -0.2953 0.2471 0.073 Uiso 1 1 calc R
H20C H 0.2724 -0.1364 0.3057 0.073 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
N1 C2 N3 118.74(11) . .
N1 C2 S1 120.76(9) . .
N3 C2 S1 120.50(10) . .
N6 C5 N4 118.12(12) . .
N6 C5 S2 120.95(9) . .
N4 C5 S2 120.93(10) . .
C13 N11 C12 117.47(12) . .
N11 C12 C13 120.00(12) . 2_545
N11 C12 C14 118.12(13) . .
C13 C12 C14 121.87(13) 2_545 .
N11 C13 C12 122.53(12) . 2_545
C23 N21 C22 117.68(12) . .
N21 C22 C23 119.97(13) . 2_645
N21 C22 C24 118.37(13) . .
C23 C22 C24 121.66(14) 2_645 .
N21 C23 C22 122.35(13) . 2_645
C33 N31 C32 116.50(12) . .
N31 C32 C33 119.58(13) . 2_676
N31 C32 C34 118.63(13) . .
C33 C32 C34 121.79(13) 2_676 .
N31 C33 C32 123.92(13) . 2_676
C43 N41 C42 117.33(11) . .
N41 C42 C43 119.69(12) . 2_776
N41 C42 C44 118.37(12) . .
C43 C42 C44 121.94(12) 2_776 .
N41 C43 C42 122.98(11) . 2_776
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C2 1.7079(12) .
N1 C2 1.3234(16) .
C2 N3 1.3359(15) .
S2 C5 1.7030(12) .
N4 C5 1.3307(16) .
C5 N6 1.3300(17) .
N11 C13 1.3316(18) .
N11 C12 1.3371(17) .
C12 C13 1.3880(19) 2_545
C12 C14 1.4974(19) .
C13 C12 1.3879(19) 2_545
N21 C23 1.3314(19) .
N21 C22 1.3361(18) .
C22 C23 1.389(2) 2_645
C22 C24 1.500(2) .
C23 C22 1.389(2) 2_645
N31 C33 1.3328(19) .
N31 C32 1.3407(18) .
C32 C33 1.3912(19) 2_676
C32 C34 1.500(2) .
C33 C32 1.3913(19) 2_676
N41 C43 1.3348(16) .
N41 C42 1.3397(16) .
C42 C43 1.3935(18) 2_776
C42 C44 1.5012(17) .
C43 C42 1.3935(18) 2_776
O1 C10 1.390(2) .
O2 C20 1.4132(18) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H01 N41 0.86(2) 2.14(2) 2.9971(15) 169.2(18) .
N1 H02 S2 0.900(18) 2.473(18) 3.3623(11) 169.7(15) 1_655
N3 H04 S2 0.89(2) 2.52(2) 3.4008(12) 173.7(16) .
N3 H03 N31 0.91(2) 2.41(2) 3.2516(16) 155.0(17) .
N4 H05 O2 0.89(2) 1.97(2) 2.8159(15) 159.1(18) .
N4 H06 S1 0.93(2) 2.44(2) 3.3649(12) 172.2(15) .
N6 H08 S1 0.87(2) 2.54(2) 3.4048(11) 174.2(17) 1_455
N6 H07 O1 0.864(18) 2.298(17) 2.9708(15) 134.8(14) .
N6 H07 O2 0.864(18) 2.484(17) 3.1663(15) 136.3(14) .
O1 H09 N11 0.84(2) 1.99(2) 2.8350(15) 175(2) .
O2 H10 N21 0.85(2) 1.98(2) 2.8233(15) 175(2) .
C24 H24B S1 0.98 2.87 3.7858(18) 156.7 2_655
C44 H44C S1 0.98 3.01 3.9861(16) 176.3 2_766
C23 H23 S2 0.95 2.94 3.8833(15) 171.4 1_545
C20 H20B S2 0.98 2.95 3.5084(16) 117.1 1_545
C43 H43 O1 0.95 2.51 3.3216(17) 143.5 1_665
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_site_symmetry_4
C13 N11 C12 C13 0.3(2) 2_545
C13 N11 C12 C14 179.83(15) .
C12 N11 C13 C12 -0.3(2) 2_545
C23 N21 C22 C23 0.5(2) 2_645
C23 N21 C22 C24 -179.95(15) .
C22 N21 C23 C22 -0.5(3) 2_645
C33 N31 C32 C33 -0.4(2) 2_676
C33 N31 C32 C34 179.69(14) .
C32 N31 C33 C32 0.4(2) 2_676
C43 N41 C42 C43 0.1(2) 2_776
C43 N41 C42 C44 179.88(13) .
C42 N41 C43 C42 -0.1(2) 2_776
