#------------------------------------------------------------------------------
#$Date: 2016-02-13 20:28:24 +0100 (Sat 13 de Feb de 2016) $
#$Revision: 176429 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/73/7117340.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_7117340
loop_
_publ_author_name
'Elena L. Harty'
'Alex R. Ha'
'Mark R. Warren'
'Amber L. Thompson'
'David R. Allan'
'Andrew L. Goodwin'
'Nicholas P. Funnell'
_publ_section_title
;
 Reversible piezochromism in a molecular wine-rack
;
_journal_name_full               Chem.Commun.
_journal_page_first              10608
_journal_paper_doi               10.1039/C5cc02916C
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration .
_chemical_compound_source        'TCI Chemicals'
_chemical_formula_moiety         'C12 H9 N3 O2 S1'
_chemical_formula_sum            'C12 H9 N3 O2 S'
_chemical_formula_weight         259.29
_chemical_name_common            ROY
_chemical_name_systematic
5-methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             14-12-16
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2015-04-07 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.38(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.116(2)
_cell_length_b                   15.1210(10)
_cell_length_c                   8.4699(16)
_cell_measurement_reflns_used    2047
_cell_measurement_temperature    293
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     1039.4(3)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'User-defined model'
_diffrn_ambient_pressure         1.49
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.517
_diffrn_measured_fraction_theta_max 0.491
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.058
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6322
_diffrn_reflns_theta_full        18.515
_diffrn_reflns_theta_max         24.686
_diffrn_reflns_theta_min         2.694
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.21
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.165
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.097
_refine_diff_density_max         0.78
_refine_diff_density_min         -0.75
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9781
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     78
_refine_ls_number_reflns         861
_refine_ls_number_restraints     64
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0759
_refine_ls_shift/su_max          0.0000803
_refine_ls_shift/su_mean         0.0000110
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.03P)² + 8.61P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1667
_refine_ls_wR_factor_gt          0.1524
_refine_ls_wR_factor_ref         0.1667
_reflns_limit_h_max              5
_reflns_limit_h_min              -7
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                654
_reflns_number_total             867
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   1.63
_oxford_diffrn_Wilson_scale      0.20
_oxford_refine_ls_r_factor_ref   0.0980
_oxford_refine_ls_scale          2.15(5)
_oxford_reflns_number_all        861
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 'ROY_Y-form, 1.49 GPa'
_cod_data_source_file            c5cc02916c3.cif
_cod_data_source_block           ROY_Y_1.49_GPa
_cod_original_cell_volume        1039.4(4)
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_original_formula_sum        'C12 H9 N3 O2 S1'
_cod_database_code               7117340
#BEGIN Tags that were not found in dictionaries:
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, 
CONT S(1,U'S) 
CONT C(2,U[ISO]) UNTIL O(15) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  18,X'S) H   ( 183,X'S) H   ( 182,X'S) H   ( 181,X'S) 
RIDE N   (   6,X'S) H   (  61,X'S) 
END    

block
CONT H(   31 ,X,Y,Z,U[ISO])
CONT H(   81 ,X,Y,Z,U[ISO])
CONT H(   91 ,X,Y,Z,U[ISO])
CONT H(  101 ,X,Y,Z,U[ISO])
CONT H(  111 ,X,Y,Z,U[ISO])
CONT H(  183 ,X,Y,Z,U[ISO])
CONT H(  182 ,X,Y,Z,U[ISO])
CONT H(  181 ,X,Y,Z,U[ISO])
CONT H(   61 ,X,Y,Z,U[ISO])
END
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
REM   DELU   START (DO NOT REMOVE THIS LINE) 
VIBR .0, 0.00200 = S(1) TO C(2) 
VIBR .0, 0.00200 = S(1) TO C(5) 
VIBR .0, 0.00500 = C(5) TO C(2) 
VIBR .0, 0.00200 = C(2) TO C(18) 
VIBR .0, 0.00200 = C(2) TO C(3) 
VIBR .0, 0.00500 = C(18) TO S(1) 
VIBR .0, 0.00500 = C(3) TO S(1) 
VIBR .0, 0.00500 = C(3) TO C(18) 
VIBR .0, 0.00200 = C(3) TO C(4) 
VIBR .0, 0.00500 = C(4) TO C(2) 
VIBR .0, 0.00200 = C(4) TO C(5) 
VIBR .0, 0.00200 = C(4) TO C(16) 
VIBR .0, 0.00500 = C(5) TO C(3) 
VIBR .0, 0.00500 = C(16) TO C(3) 
VIBR .0, 0.00500 = C(16) TO C(5) 
VIBR .0, 0.00200 = C(5) TO N(6) 
VIBR .0, 0.00500 = S(1) TO C(4) 
VIBR .0, 0.00500 = N(6) TO C(4) 
VIBR .0, 0.00500 = N(6) TO S(1) 
VIBR .0, 0.00200 = N(6) TO C(7) 
VIBR .0, 0.00500 = C(7) TO C(5) 
VIBR .0, 0.00200 = C(7) TO C(8) 
VIBR .0, 0.00200 = C(7) TO C(12) 
VIBR .0, 0.00500 = C(8) TO N(6) 
VIBR .0, 0.00500 = C(12) TO N(6) 
VIBR .0, 0.00500 = C(12) TO C(8) 
VIBR .0, 0.00200 = C(8) TO C(9) 
VIBR .0, 0.00500 = C(9) TO C(7) 
VIBR .0, 0.00200 = C(9) TO C(10) 
VIBR .0, 0.00500 = C(10) TO C(8) 
VIBR .0, 0.00200 = C(10) TO C(11) 
VIBR .0, 0.00500 = C(11) TO C(9) 
VIBR .0, 0.00200 = C(11) TO C(12) 
VIBR .0, 0.00500 = C(12) TO C(10) 
VIBR .0, 0.00200 = C(12) TO N(13) 
VIBR .0, 0.00500 = C(7) TO C(11) 
VIBR .0, 0.00500 = N(13) TO C(11) 
VIBR .0, 0.00500 = N(13) TO C(7) 
VIBR .0, 0.00200 = N(13) TO O(14) 
VIBR .0, 0.00200 = N(13) TO O(15) 
VIBR .0, 0.00500 = O(14) TO C(12) 
VIBR .0, 0.00500 = O(15) TO C(12) 
VIBR .0, 0.00500 = O(15) TO O(14) 
VIBR .0, 0.00200 = C(16) TO N(17) 
VIBR .0, 0.00500 = N(17) TO C(4) 
REM   DELU   END (DO NOT REMOVE THIS LINE) 
REM   THERMSIM   START (DO NOT REMOVE THIS LINE) 
U(IJ) .0, 0.04000 = S(1) TO C(2) 
U(IJ) .0, 0.04000 = S(1) TO C(5) 
U(IJ) .0, 0.08000 = C(2) TO C(18) 
U(IJ) .0, 0.04000 = C(2) TO C(3) 
U(IJ) .0, 0.04000 = C(3) TO C(4) 
U(IJ) .0, 0.04000 = C(4) TO C(5) 
U(IJ) .0, 0.04000 = C(4) TO C(16) 
U(IJ) .0, 0.04000 = C(5) TO N(6) 
U(IJ) .0, 0.04000 = N(6) TO C(7) 
U(IJ) .0, 0.04000 = C(7) TO C(8) 
U(IJ) .0, 0.04000 = C(7) TO C(12) 
U(IJ) .0, 0.04000 = C(8) TO C(9) 
U(IJ) .0, 0.04000 = C(9) TO C(10) 
U(IJ) .0, 0.04000 = C(10) TO C(11) 
U(IJ) .0, 0.04000 = C(11) TO C(12) 
U(IJ) .0, 0.04000 = C(12) TO N(13) 
U(IJ) .0, 0.08000 = N(13) TO O(14) 
U(IJ) .0, 0.08000 = N(13) TO O(15) 
U(IJ) .0, 0.08000 = C(16) TO N(17) 
REM   THERMSIM   END (DO NOT REMOVE THIS LINE) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
DISTANCE 1.220000 , 0.020000 = N(13) TO O(14) 
DISTANCE 1.220000 , 0.020000 = N(13) TO O(15) 
DISTANCE 1.450000 , 0.020000 = C(12) TO N(13) 
DISTANCE 1.390000 , 0.020000 = C(11) TO C(12) 
DISTANCE 1.360000 , 0.020000 = C(10) TO C(11) 
DISTANCE 1.390000 , 0.020000 = C(9) TO C(10) 
DISTANCE 1.370000 , 0.020000 = C(8) TO C(9) 
DISTANCE 1.400000 , 0.020000 = C(7) TO C(8) 
DISTANCE 1.410000 , 0.020000 = C(7) TO C(12) 
DISTANCE 1.370000 , 0.020000 = C(7) TO N(6) 
DISTANCE 1.400000 , 0.02000 = C(5) TO N(6) 
DISTANCE 1.720000 , 0.020000 = S(1) TO C(5) 
DISTANCE 1.720000 , 0.020000 = S(1) TO C(2) 
DISTANCE 1.350000 , 0.020000 = C(2) TO C(3) 
DISTANCE 1.430000 , 0.020000 = C(3) TO C(4) 
DISTANCE 1.360000 , 0.020000 = C(4) TO C(5) 
DISTANCE 1.430000 , 0.020000 = C(4) TO C(16) 
DISTANCE 1.140000 , 0.020000 = C(16) TO N(17) 
DISTANCE 1.500000 , 0.020000 = C(2) TO C(18) 
END            

REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 3) to H(31) 
REST 0.032, 0.002 = H(31,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(31) TO C ( 3) TO C(2) 
CONT H(31) TO C ( 3) TO C(4) 
PLANAR C ( 3) C(2) C(4) H(31) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 8) to H(81) 
REST 0.034, 0.002 = H(81,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(81) TO C ( 8) TO C(7) 
CONT H(81) TO C ( 8) TO C(9) 
PLANAR C ( 8) C(7) C(9) H(81) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 9) to H(91) 
REST 0.039, 0.002 = H(91,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(91) TO C ( 9) TO C(8) 
CONT H(91) TO C ( 9) TO C(10) 
PLANAR C ( 9) C(8) C(10) H(91) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 10) to H(101) 
REST 0.038, 0.002 = H(101,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(101) TO C ( 10) TO C(9) 
CONT H(101) TO C ( 10) TO C(11) 
PLANAR C ( 10) C(9) C(11) H(101) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 11) to H(111) 
REST 0.034, 0.002 = H(111,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(111) TO C ( 11) TO C(10) 
CONT H(111) TO C ( 11) TO C(12) 
PLANAR C ( 11) C(10) C(12) H(111) 
REM            3 H on sp 3
DIST 0.96, 0.02 = 
CONT C ( 18) to H(183) 
CONT C ( 18) to H(182) 
CONT C ( 18) to H(181) 
REST 0.041, 0.002 = H(183,U[ISO]) 
REST 0.041, 0.002 = H(182,U[ISO]) 
REST 0.041, 0.002 = H(181,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(2) to C ( 18) to H(183) 
CONT C(2) to C ( 18) to H(182) 
CONT C(2) to C ( 18) to H(181) 
ANGLE 0.0, 2.0 = mean H(183) to C ( 18) to H(182) 
CONT H(183) to C ( 18) to H(181) 
CONT H(182) to C ( 18) to H(181) 
REM            H1-N-R2
DIST 0.86, 0.02 = 
CONT N ( 6) to H(61) 
REST 0.030, 0.002 = H(61,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(61) TO N ( 6) TO C(5) 
CONT H(61) TO N ( 6) TO C(7) 
PLANAR 0.010000  C(5) C(7) N(6) H(61) 
END
;
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
S1 S 0.8094(4) 0.38422(11) 0.1110(3) 0.0304 1.0000 Uani D U . . . .
C2 C 1.0074(13) 0.3457(4) 0.0823(11) 0.0274(12) 1.0000 Uiso D U . . . .
C3 C 1.0628(14) 0.3009(4) 0.2083(11) 0.0265(12) 1.0000 Uiso D U . . . .
C4 C 0.9441(13) 0.2974(4) 0.3326(11) 0.0261(11) 1.0000 Uiso D U . . . .
C5 C 0.8034(13) 0.3400(4) 0.2968(11) 0.0244(11) 1.0000 Uiso D U . . . .
C7 C 0.6501(13) 0.3947(4) 0.5255(11) 0.0255(11) 1.0000 Uiso D U . . . .
C8 C 0.7902(14) 0.4342(4) 0.5922(11) 0.0286(12) 1.0000 Uiso D U . . . .
C9 C 0.7835(15) 0.4856(4) 0.7260(12) 0.0323(13) 1.0000 Uiso D U . . . .
C10 C 0.6347(14) 0.4978(5) 0.8030(12) 0.0319(13) 1.0000 Uiso D U . . . .
C11 C 0.4967(14) 0.4596(4) 0.7457(11) 0.0284(12) 1.0000 Uiso D U . . . .
C12 C 0.5026(13) 0.4077(4) 0.6104(11) 0.0282(11) 1.0000 Uiso D U . . . .
C16 C 0.9677(15) 0.2533(4) 0.4806(11) 0.0290(13) 1.0000 Uiso D U . . . .
C18 C 1.0892(16) 0.3647(4) -0.0724(12) 0.0272(14) 1.0000 Uiso D U . . . .
N6 N 0.6554(12) 0.3479(3) 0.3851(9) 0.0245(11) 1.0000 Uiso D U . . . .
N13 N 0.3465(12) 0.3736(4) 0.5496(10) 0.0325(11) 1.0000 Uiso D U . . . .
N17 N 0.9745(13) 0.2181(4) 0.6004(10) 0.0350(14) 1.0000 Uiso D U . . . .
O14 O 0.2189(11) 0.3976(3) 0.6164(9) 0.0400(12) 1.0000 Uiso D U . . . .
O15 O 0.3437(11) 0.3212(3) 0.4391(9) 0.0395(12) 1.0000 Uiso D U . . . .
H31 H 1.1662 0.2754 0.2152 0.0318 1.0000 Uiso R . . . . .
H61 H 0.5679 0.3232 0.3503 0.0301 1.0000 Uiso R . . . . .
H81 H 0.8910 0.4258 0.5439 0.0338 1.0000 Uiso R . . . . .
H91 H 0.8799 0.5121 0.7633 0.0392 1.0000 Uiso R . . . . .
H101 H 0.6286 0.5325 0.8950 0.0383 1.0000 Uiso R . . . . .
H111 H 0.3956 0.4670 0.7972 0.0342 1.0000 Uiso R . . . . .
H181 H 1.1995 0.3423 -0.0679 0.0410 1.0000 Uiso R . . . . .
H182 H 1.0915 0.4266 -0.0920 0.0409 1.0000 Uiso R . . . . .
H183 H 1.0292 0.3353 -0.1554 0.0408 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.038(2) 0.0291(9) 0.0245(17) 0.0038(9) 0.0089(18) 0.0045(10)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . S1 . C5 . 91.7(5) yes
S1 . C2 . C3 . 111.4(5) yes
S1 . C2 . C18 . 118.4(8) yes
C3 . C2 . C18 . 130.2(9) yes
C2 . C3 . C4 . 112.4(9) yes
C2 . C3 . H31 . 124.1 no
C4 . C3 . H31 . 123.5 no
C3 . C4 . C5 . 113.0(8) yes
C3 . C4 . C16 . 125.0(9) yes
C5 . C4 . C16 . 122.0(7) yes
S1 . C5 . C4 . 111.5(5) yes
S1 . C5 . N6 . 118.6(8) yes
C4 . C5 . N6 . 129.7(8) yes
C8 . C7 . C12 . 115.0(8) yes
C8 . C7 . N6 . 122.4(7) yes
C12 . C7 . N6 . 122.6(9) yes
C7 . C8 . C9 . 122.5(8) yes
C7 . C8 . H81 . 118.7 no
C9 . C8 . H81 . 118.8 no
C8 . C9 . C10 . 120.1(11) yes
C8 . C9 . H91 . 118.9 no
C10 . C9 . H91 . 121.0 no
C9 . C10 . C11 . 119.8(9) yes
C9 . C10 . H101 . 120.9 no
C11 . C10 . H101 . 119.3 no
C10 . C11 . C12 . 120.3(8) yes
C10 . C11 . H111 . 120.5 no
C12 . C11 . H111 . 119.1 no
C7 . C12 . C11 . 122.1(10) yes
C7 . C12 . N13 . 120.5(8) yes
C11 . C12 . N13 . 117.1(7) yes
C4 . C16 . N17 . 175.1(11) yes
C2 . C18 . H181 . 108.4 no
C2 . C18 . H182 . 110.5 no
H181 . C18 . H182 . 109.6 no
C2 . C18 . H183 . 109.0 no
H181 . C18 . H183 . 109.6 no
H182 . C18 . H183 . 109.8 no
C5 . N6 . C7 . 121.6(9) yes
C5 . N6 . H61 . 119.0 no
C7 . N6 . H61 . 119.4 no
C12 . N13 . O14 . 117.5(7) yes
C12 . N13 . O15 . 120.6(7) yes
O14 . N13 . O15 . 121.8(10) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . C2 . 1.729(10) yes
S1 . C5 . 1.710(8) yes
C2 . C3 . 1.339(13) yes
C2 . C18 . 1.501(9) yes
C3 . C4 . 1.433(8) yes
C3 . H31 . 0.926 no
C4 . C5 . 1.344(13) yes
C4 . C16 . 1.431(12) yes
C5 . N6 . 1.425(9) yes
C7 . C8 . 1.400(14) yes
C7 . C12 . 1.414(10) yes
C7 . N6 . 1.385(10) yes
C8 . C9 . 1.375(11) yes
C8 . H81 . 0.926 no
C9 . C10 . 1.388(11) yes
C9 . H91 . 0.932 no
C10 . C11 . 1.348(15) yes
C10 . H101 . 0.941 no
C11 . C12 . 1.390(11) yes
C11 . H111 . 0.938 no
C12 . N13 . 1.459(13) yes
C16 . N17 . 1.147(11) yes
C18 . H181 . 0.958 no
C18 . H182 . 0.950 no
C18 . H183 . 0.961 no
N6 . H61 . 0.853 no
N13 . O14 . 1.238(8) yes
N13 . O15 . 1.226(9) yes
