#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:31:23 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258043 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/00/7240094.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_7240094
loop_
_publ_author_name
'El-Emam, Ali A.'
'Saveeth Kumar, Elangovan'
'Janani, Krishnakumar'
'Al-Wahaibi, Lamya H.'
'Blacque, Olivier'
'El-Awady, Mohamed I.'
'Al-Shaalan, Nora H.'
'Percino, M. Judith'
'Thamotharan, Subbiah'
_publ_section_title
;
 Quantitative assessment of the nature of noncovalent interactions in
 N-substituted-5-(adamantan-1-yl)-1,3,4-thiadiazole-2-amines: insights
 from crystallographic and QTAIM analysis
;
_journal_issue                   17
_journal_name_full               'RSC Advances'
_journal_page_first              9840
_journal_page_last               9853
_journal_paper_doi               10.1039/D0RA00733A
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C14 H21 N3 S'
_chemical_formula_sum            'C14 H21 N3 S'
_chemical_formula_weight         263.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-14 deposited with the CCDC.	2020-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.464(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8339(2)
_cell_length_b                   15.8974(2)
_cell_length_c                   9.4749(2)
_cell_measurement_reflns_used    12263
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      79.1
_cell_measurement_theta_min      5.1
_cell_volume                     1348.26(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  25.00   0.50    0.50    --  -54.56  19.00  60.00  102
  2  ω   -127.00 -33.00   0.50    0.50    --  -54.56 -77.00 120.00  188
  3  ω   -130.00 -82.00   0.50    0.50    --  -54.56 -99.00 150.00   96
  4  ω   -130.00 -82.00   0.50    0.50    --  -54.56 -99.00   0.00   96
  5  ω   -130.00 -82.00   0.50    0.50    --  -54.56 -99.00 -60.00   96
  6  ω   -163.00 -78.00   0.50    2.00    --  -86.25-111.00-150.00  170
  7  ω     98.00 178.00   0.50    2.00    --  107.75 113.00  69.65  160
  8  ω    153.00 178.00   0.50    2.00    --  107.75  45.00  30.00   50
  9  ω    127.00 177.00   0.50    2.00    --  107.75 111.00 -60.00  100
 10  ω    129.00 178.00   0.50    2.00    --  107.75 111.00 -90.00   98
 11  ω    117.00 143.00   0.50    2.00    --  107.75  45.00 -90.00   52
 12  ω    107.00 176.00   0.50    2.00    --  107.75  61.00 -90.00  138
 13  ω     98.00 178.00   0.50    2.00    --  107.75  15.00   0.00  160
 14  ω    100.00 178.00   0.50    2.00    --  107.75  61.00   0.00  156
 15  ω     99.00 134.00   0.50    2.00    --  107.75  15.00  90.00   70
 16  ω    104.00 129.00   0.50    2.00    --  107.75  45.00 150.00   50
 17  ω    131.00 168.00   0.50    2.00    --  107.75  45.00 150.00   74
 18  ω    100.00 126.00   0.50    2.00    --  107.75  45.00  30.00   52
 19  ω     88.00 178.00   0.50    2.00    --  107.75  73.00 -48.67  180
 20  ω     78.00 110.00   0.50    2.00    --  107.75 -78.00  84.85   64
 21  ω     82.00 111.00   0.50    2.00    --  107.75-111.00 120.00   58
 22  ω     54.00  81.00   0.50    2.00    --  107.75 -77.00 120.00   54
 23  ω     53.00  90.00   0.50    2.00    --  107.75-111.00  90.00   74
 24  ω     38.00  67.00   0.50    2.00    --  107.75 -78.00  84.85   58
 25  ω     32.00  58.00   0.50    2.00    --  107.75-111.00 120.00   52
 26  ω     40.00  66.00   0.50    2.00    --  107.75 -61.00 -30.00   52
 27  ω     53.00  79.00   0.50    2.00    --  107.75 -94.00 -60.00   52
 28  ω     85.00 111.00   0.50    2.00    --  107.75-111.00 -90.00   52
 29  ω     78.00 103.00   0.50    2.00    --  107.75 -94.00 -30.00   50
 30  ω     41.00  71.00   0.50    2.00    --  107.75 -61.00-120.00   60
 31  ω     58.00 104.00   0.50    2.00    --  107.75 -77.00-150.00   92
 32  ω     75.00 103.00   0.50    2.00    --  107.75 -94.00-180.00   56
 33  ω     66.00  97.00   0.50    2.00    --  107.75 -77.00-180.00   62
 34  ω     41.00  75.00   0.50    2.00    --  107.75-111.00 -90.00   68
 35  ω     35.00  61.00   0.50    2.00    --  107.75 -55.00-118.00   52
 36  ω     88.00 138.00   0.50    2.00    --  107.75  73.00 179.37  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1538168000
_diffrn_orient_matrix_UB_12      0.0433428000
_diffrn_orient_matrix_UB_13      0.0604804000
_diffrn_orient_matrix_UB_21      0.0473689000
_diffrn_orient_matrix_UB_22      -0.0470466000
_diffrn_orient_matrix_UB_23      0.1552494000
_diffrn_orient_matrix_UB_31      0.0609542000
_diffrn_orient_matrix_UB_32      -0.0728009000
_diffrn_orient_matrix_UB_33      -0.0644067000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15881
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.304
_diffrn_reflns_theta_min         5.566
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.006
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0422P)²+0.4756P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0839
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2798
_reflns_number_total             2920
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra00733a2.cif
_cod_data_source_block           emam4
_cod_depositor_comments
'Adding full bibliography for 7240094--7240096.cif.'
_cod_database_code               7240094
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.740
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B),
 C13(H13A,H13B), C14(H14A,H14B)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.41975(14) 0.90571(8) 0.40653(15) 0.0302(3) Uani 1 1 d . . . . .
H1A H 0.346606 0.871791 0.323276 0.045 Uiso 1 1 calc GR . . . .
H1B H 0.486103 0.934095 0.367966 0.045 Uiso 1 1 calc GR . . . .
H1C H 0.367439 0.947812 0.441185 0.045 Uiso 1 1 calc GR . . . .
C2 C 0.51126(14) 0.84908(7) 0.54148(14) 0.0263(2) Uani 1 1 d . . . . .
H2A H 0.582988 0.883416 0.627139 0.032 Uiso 1 1 calc R . . . .
H2B H 0.444403 0.819943 0.580114 0.032 Uiso 1 1 calc R . . . .
C3 C 0.63954(12) 0.71429(7) 0.56786(12) 0.0212(2) Uani 1 1 d . . . . .
C4 C 0.73196(12) 0.57441(7) 0.65329(12) 0.0210(2) Uani 1 1 d . . . . .
C5 C 0.79660(12) 0.48687(7) 0.67840(12) 0.0211(2) Uani 1 1 d . . . . .
C6 C 0.71519(14) 0.43205(8) 0.53367(14) 0.0298(3) Uani 1 1 d . . . . .
H6A H 0.607461 0.429291 0.510592 0.036 Uiso 1 1 calc R . . . .
H6B H 0.725594 0.457586 0.443357 0.036 Uiso 1 1 calc R . . . .
C7 C 0.78137(15) 0.34279(8) 0.56100(16) 0.0340(3) Uani 1 1 d . . . . .
H7 H 0.727013 0.307662 0.466733 0.041 Uiso 1 1 calc R . . . .
C8 C 0.94647(17) 0.34728(9) 0.59248(19) 0.0394(3) Uani 1 1 d . . . . .
H8A H 0.957557 0.372639 0.502384 0.047 Uiso 1 1 calc R . . . .
H8B H 0.989360 0.289905 0.608244 0.047 Uiso 1 1 calc R . . . .
C9 C 1.02982(14) 0.40065(8) 0.73747(18) 0.0369(3) Uani 1 1 d . . . . .
H9 H 1.138133 0.403449 0.758583 0.044 Uiso 1 1 calc R . . . .
C10 C 0.96392(13) 0.49008(8) 0.71165(16) 0.0305(3) Uani 1 1 d . . . . .
H10A H 0.976265 0.516545 0.623092 0.037 Uiso 1 1 calc R . . . .
H10B H 1.018225 0.524713 0.805061 0.037 Uiso 1 1 calc R . . . .
C11 C 0.76561(15) 0.30314(8) 0.69995(17) 0.0345(3) Uani 1 1 d . . . . .
H11A H 0.808310 0.245699 0.717331 0.041 Uiso 1 1 calc R . . . .
H11B H 0.658572 0.298850 0.679236 0.041 Uiso 1 1 calc R . . . .
C12 C 0.84708(15) 0.35676(8) 0.84400(15) 0.0314(3) Uani 1 1 d . . . . .
H12 H 0.835708 0.330635 0.934512 0.038 Uiso 1 1 calc R . . . .
C13 C 0.77919(14) 0.44539(8) 0.81653(14) 0.0282(3) Uani 1 1 d . . . . .
H13A H 0.830048 0.480027 0.910719 0.034 Uiso 1 1 calc R . . . .
H13B H 0.671948 0.441955 0.795357 0.034 Uiso 1 1 calc R . . . .
C14 C 1.01257(15) 0.36092(8) 0.87685(17) 0.0375(3) Uani 1 1 d . . . . .
H14A H 1.055731 0.303579 0.895343 0.045 Uiso 1 1 calc R . . . .
H14B H 1.066852 0.395033 0.970974 0.045 Uiso 1 1 calc R . . . .
N1 N 0.59200(11) 0.78731(7) 0.49242(12) 0.0265(2) Uani 1 1 d . . . . .
H1 H 0.5989(18) 0.7935(10) 0.403(2) 0.035(4) Uiso 1 1 d . . . . .
N2 N 0.63208(11) 0.69338(6) 0.69847(11) 0.0247(2) Uani 1 1 d . . . . .
N3 N 0.68498(11) 0.61215(6) 0.74506(11) 0.0247(2) Uani 1 1 d . . . . .
S1 S 0.71497(3) 0.63569(2) 0.49303(3) 0.02678(10) Uani 1 1 d . . . . .
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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0244
-1 0 0 0.0295
0 -1 1 0.0580
0 1 -1 0.0837
1 -1 -2 0.0620
-1 2 1 0.0618
1 -2 -1 0.0590
0 -2 -1 0.0582
1 2 -1 0.0705
-1 -2 1 0.0763
0 1 0 0.0572
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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.2 . . ?
N1 C2 C1 110.05(10) . . ?
N1 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
N1 C3 S1 121.04(8) . . ?
N2 C3 N1 125.32(10) . . ?
N2 C3 S1 113.62(8) . . ?
C5 C4 S1 122.18(8) . . ?
N3 C4 C5 124.65(10) . . ?
N3 C4 S1 113.17(8) . . ?
C4 C5 C6 110.62(9) . . ?
C4 C5 C10 110.25(9) . . ?
C4 C5 C13 110.01(9) . . ?
C6 C5 C10 108.53(10) . . ?
C13 C5 C6 108.37(10) . . ?
C13 C5 C10 109.01(9) . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 C5 110.16(10) . . ?
C7 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C6 C7 H7 109.4 . . ?
C8 C7 C6 109.37(11) . . ?
C8 C7 H7 109.4 . . ?
C11 C7 C6 109.86(11) . . ?
C11 C7 H7 109.4 . . ?
C11 C7 C8 109.33(11) . . ?
C7 C8 H8A 109.8 . . ?
C7 C8 H8B 109.8 . . ?
C7 C8 C9 109.39(11) . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
C8 C9 H9 109.5 . . ?
C8 C9 C10 109.59(11) . . ?
C8 C9 C14 109.56(11) . . ?
C10 C9 H9 109.5 . . ?
C14 C9 H9 109.5 . . ?
C14 C9 C10 109.11(12) . . ?
C5 C10 H10A 109.6 . . ?
C5 C10 H10B 109.6 . . ?
C9 C10 C5 110.19(9) . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C7 C11 H11A 109.7 . . ?
C7 C11 H11B 109.7 . . ?
C7 C11 C12 109.77(10) . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C11 C12 H12 109.4 . . ?
C11 C12 C13 109.33(10) . . ?
C11 C12 C14 109.10(11) . . ?
C13 C12 H12 109.4 . . ?
C14 C12 H12 109.4 . . ?
C14 C12 C13 110.31(10) . . ?
C5 C13 H13A 109.6 . . ?
C5 C13 H13B 109.6 . . ?
C12 C13 C5 110.14(10) . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C9 C14 H14A 109.8 . . ?
C9 C14 H14B 109.8 . . ?
C12 C14 C9 109.30(10) . . ?
C12 C14 H14A 109.8 . . ?
C12 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
C2 N1 H1 120.1(11) . . ?
C3 N1 C2 121.98(10) . . ?
C3 N1 H1 117.3(11) . . ?
C3 N2 N3 111.96(9) . . ?
C4 N3 N2 114.11(9) . . ?
C3 S1 C4 87.14(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
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.5173(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 N1 1.4548(15) . ?
C3 N1 1.3418(15) . ?
C3 N2 1.3125(14) . ?
C3 S1 1.7463(11) . ?
C4 C5 1.5073(15) . ?
C4 N3 1.2892(14) . ?
C4 S1 1.7529(11) . ?
C5 C6 1.5401(15) . ?
C5 C10 1.5427(15) . ?
C5 C13 1.5371(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5377(18) . ?
C7 H7 1.0000 . ?
C7 C8 1.526(2) . ?
C7 C11 1.524(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.532(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.5395(17) . ?
C9 C14 1.535(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5250(19) . ?
C12 H12 1.0000 . ?
C12 C13 1.5344(17) . ?
C12 C14 1.526(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N1 H1 0.884(18) . ?
N2 N3 1.3939(13) . ?
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
_geom_hbond_publ_flag
N1 H1 N2 0.884(18) 2.103(18) 2.9859(14) 175.8(15) 4_575 yes
N1 H1 N3 0.884(18) 2.500(17) 3.2647(14) 145.0(14) 4_575 yes
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 N1 C3 -157.26(11) . . . . ?
C3 N2 N3 C4 0.84(14) . . . . ?
C4 C5 C6 C7 -179.64(10) . . . . ?
C4 C5 C10 C9 179.93(10) . . . . ?
C4 C5 C13 C12 -179.12(9) . . . . ?
C5 C4 N3 N2 179.06(9) . . . . ?
C5 C4 S1 C3 -179.53(9) . . . . ?
C5 C6 C7 C8 -60.70(14) . . . . ?
C5 C6 C7 C11 59.30(14) . . . . ?
C6 C5 C10 C9 -58.77(13) . . . . ?
C6 C5 C13 C12 59.82(12) . . . . ?
C6 C7 C8 C9 60.50(14) . . . . ?
C6 C7 C11 C12 -59.36(14) . . . . ?
C7 C8 C9 C10 -60.10(15) . . . . ?
C7 C8 C9 C14 59.59(14) . . . . ?
C7 C11 C12 C13 59.90(14) . . . . ?
C7 C11 C12 C14 -60.82(13) . . . . ?
C8 C7 C11 C12 60.67(14) . . . . ?
C8 C9 C10 C5 59.67(14) . . . . ?
C8 C9 C14 C12 -59.83(14) . . . . ?
C10 C5 C6 C7 59.29(13) . . . . ?
C10 C5 C13 C12 -58.12(13) . . . . ?
C10 C9 C14 C12 60.15(14) . . . . ?
C11 C7 C8 C9 -59.82(14) . . . . ?
C11 C12 C13 C5 -60.69(13) . . . . ?
C11 C12 C14 C9 60.16(13) . . . . ?
C13 C5 C6 C7 -58.97(13) . . . . ?
C13 C5 C10 C9 59.08(13) . . . . ?
C13 C12 C14 C9 -59.96(14) . . . . ?
C14 C9 C10 C5 -60.30(14) . . . . ?
C14 C12 C13 C5 59.29(14) . . . . ?
N1 C3 N2 N3 177.61(11) . . . . ?
N1 C3 S1 C4 -178.04(10) . . . . ?
N2 C3 N1 C2 -6.50(18) . . . . ?
N2 C3 S1 C4 0.46(9) . . . . ?
N3 C4 C5 C6 127.09(12) . . . . ?
N3 C4 C5 C10 -112.87(12) . . . . ?
N3 C4 C5 C13 7.39(15) . . . . ?
N3 C4 S1 C3 0.03(9) . . . . ?
S1 C3 N1 C2 171.81(9) . . . . ?
S1 C3 N2 N3 -0.81(12) . . . . ?
S1 C4 C5 C6 -53.40(12) . . . . ?
S1 C4 C5 C10 66.64(11) . . . . ?
S1 C4 C5 C13 -173.10(8) . . . . ?
S1 C4 N3 N2 -0.49(12) . . . . ?
