#------------------------------------------------------------------------------
#$Date: 2022-09-09 04:53:18 +0300 (Fri, 09 Sep 2022) $
#$Revision: 277749 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/41/2244161.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2244161
loop_
_publ_author_name
'Mutalliev, Lukmonjon Z.'
'Abdullaev, Sirojiddin'
'Pirnazarova, Nasiba'
'Obidova, Ibodat'
'Turgunov, Kambarali'
'Yakubov, Ubaydullo'
'Ashurov, Jamshid M.'
'Elmuradov, Burkhan Zh.'
'Mamadrakhimov, Azimjon A.'
_publ_section_title
;
Synthesis, crystal structure and Hirshfeld surface analysis of
(1H-benzimidazol-2-yl)(morpholin-4-yl)methanethione
;
_journal_coeditor_code WM5654
_journal_issue 10
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi 10.1107/S2056989022008933
_journal_volume 78
_journal_year 2022
_chemical_formula_iupac 'C12 H13 N3 O S'
_chemical_formula_moiety 'C12 H13 N3 O S'
_chemical_formula_sum 'C12 H13 N3 O S'
_chemical_formula_weight 247.31
_chemical_melting_point 513(2)
_chemical_name_common
;
2-[(Morpholin-4-yl)carbothioyl]-1H-1,3-benzodiazole
;
_chemical_name_systematic
;
(1H-Benzimidazol-2-yl)(morpholin-4-yl)methanethione
;
_space_group_crystal_system monoclinic
_space_group_IT_number 9
_space_group_name_Hall 'I -2ya'
_space_group_name_H-M_alt 'I 1 a 1'
_atom_sites_solution_hydrogens mixed
_audit_creation_method SHELXL-2014/7
_cell_angle_alpha 90
_cell_angle_beta 106.661(2)
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 8.1644(2)
_cell_length_b 15.9237(3)
_cell_length_c 9.6936(2)
_cell_measurement_reflns_used 4375
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 71.1310
_cell_measurement_theta_min 5.4640
_cell_volume 1207.33(5)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_molecular_graphics
;
XP (Siemens, 1994), Mercury (Macrae et al. 2020)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature 293(2)
_diffrn_detector 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator mirror
_diffrn_radiation_probe x-ray
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_wavelength 1.54184
_diffrn_reflns_av_R_equivalents 0.0217
_diffrn_reflns_av_unetI/netI 0.0202
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 19
_diffrn_reflns_limit_k_min -19
_diffrn_reflns_limit_l_max 11
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_number 5160
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 71.270
_diffrn_reflns_theta_min 5.515
_diffrn_source 'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu 2.280
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.56821
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2020)
;
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.361
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description needle
_exptl_crystal_F_000 520
_exptl_crystal_size_max .30
_exptl_crystal_size_mid .25
_exptl_crystal_size_min .14
_refine_diff_density_max 0.172
_refine_diff_density_min -0.191
_refine_ls_abs_structure_details
;
Flack x determined using 531 quotients
[(I^+^)-(I^-^)]/[(I^+^)+(I^-^)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack -0.001(13)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.101
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 189
_refine_ls_number_reflns 1724
_refine_ls_number_restraints 2
_refine_ls_restrained_S_all 1.100
_refine_ls_R_factor_all 0.0305
_refine_ls_R_factor_gt 0.0301
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0448P)^2^+0.2955P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0781
_refine_ls_wR_factor_ref 0.0786
_reflns_number_gt 1692
_reflns_number_total 1724
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file wm5654sup1.cif
_cod_data_source_block I
_cod_original_sg_symbol_H-M 'I a'
_cod_database_code 2244161
_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_hkl_file
;
-9 0 -1 0.08 0.38
-9 0 1 0.24 0.40
-9 0 3 0.27 0.47
-9 0 5 0.37 0.49
-9 -1 0 4.02 0.92
-9 1 0 3.12 0.84
-9 1 2 45.52 3.17
-9 -1 2 44.54 3.17
-9 1 4 82.40 4.33
-9 -1 4 80.32 4.32
-9 1 6 18.77 1.87
-9 2 -1 27.64 2.02
-9 -2 1 44.25 2.97
-9 2 1 42.01 2.90
-9 -2 3 6.21 1.25
-9 2 3 8.52 1.43
-9 2 5 3.78 0.89
-9 -2 5 3.53 0.95
-9 2 7 9.03 1.01
-9 3 0 0.29 0.40
-9 3 2 25.18 2.26
-9 -3 2 22.72 2.20
-9 -3 4 5.50 1.16
-9 3 6 24.93 2.01
-9 4 -1 38.86 2.22
-9 -4 -1 39.58 2.30
-9 4 1 31.19 2.33
-9 -4 3 24.91 2.22
-9 -4 5 93.09 4.28
-9 4 7 21.88 1.49
-9 5 0 33.92 2.14
-9 -5 0 29.86 2.04
-9 -5 4 4.04 0.92
-9 5 6 18.01 1.60
-9 6 5 5.63 0.93
-9 7 4 17.54 1.55
-8 0 -2 9.76 1.40
-8 0 0 12.43 1.79
-8 0 2 22.05 2.55
-8 0 4 404.49 12.21
-8 0 6 409.35 11.08
-8 0 6 421.10 12.34
-8 0 8 10.88 1.32
-8 1 -3 3.82 0.83
-8 1 -1 8.34 1.42
-8 -1 -1 10.21 1.56
-8 -1 1 36.75 3.16
-8 1 1 33.11 2.95
-8 1 3 88.65 5.18
-8 -1 3 96.88 5.42
-8 1 5 19.76 2.54
-8 -1 5 20.84 2.62
-8 1 7 22.86 2.32
-8 -1 7 21.25 1.95
-8 1 9 14.27 1.32
-8 -1 9 16.23 1.37
-8 2 -2 52.95 3.20
-8 -2 0 47.77 3.42
-8 2 0 47.61 3.39
-8 -2 2 46.97 3.65
-8 2 2 51.25 3.73
-8 -2 4 53.07 4.05
-8 2 4 56.36 4.10
-8 2 6 9.11 1.55
-8 -2 6 8.14 1.67
-8 2 8 31.46 2.22
-8 -2 8 30.82 2.13
-8 3 -3 3.89 0.81
-8 3 -1 40.41 2.92
-8 -3 1 48.38 3.58
-8 3 1 54.62 3.69
-8 -3 3 1.35 0.82
-8 3 3 0.96 0.63
-8 -3 5 47.87 3.77
-8 3 5 51.26 3.61
-8 -3 7 31.99 2.30
-8 3 7 29.51 2.32
-8 -3 9 6.25 0.89
-8 3 9 6.54 0.87
-8 3 9 7.89 0.95
-8 4 -2 3.26 0.87
-8 4 0 39.29 2.96
-8 4 2 15.86 2.06
-8 -4 2 20.89 2.41
-8 -4 4 56.18 4.00
-8 4 4 51.13 3.64
-8 4 6 53.32 3.55
-8 4 8 -0.09 0.29
-8 -4 8 0.37 0.35
-8 -5 -3 4.46 0.81
-8 5 -3 5.28 0.84
-8 5 -1 65.37 3.56
-8 5 1 15.91 1.92
-8 -5 3 80.31 4.63
-8 5 5 38.85 3.11
-8 -5 5 42.23 3.32
-8 5 7 23.68 2.04
-8 5 7 27.55 2.38
-8 6 -2 1.05 0.46
-8 -6 -2 1.39 0.61
-8 -6 0 69.61 4.03
-8 6 4 69.38 4.14
-8 6 6 95.27 4.65
-8 6 8 36.45 2.20
-8 -7 -1 4.22 0.98
-8 -7 1 2.97 0.88
-8 7 3 9.93 1.58
-8 7 5 13.93 1.78
-8 7 7 26.04 1.96
-8 7 7 35.45 2.40
-8 -8 -2 1.44 0.50
-8 -8 0 16.79 1.79
-8 8 4 1.13 0.61
-8 8 6 3.18 0.79
-8 -9 -1 2.52 0.67
-8 -9 1 8.27 1.20
-8 9 3 4.37 1.01
-8 9 5 7.06 1.14
-8 -9 7 2.11 0.56
-8 9 7 11.35 1.09
-8 -10 0 9.85 1.17
-8 10 2 0.38 0.34
-8 10 4 3.92 0.87
-8 10 6 7.00 0.92
-8 -10 6 0.13 0.25
-8 -11 1 9.32 1.03
-8 11 3 60.53 2.98
-8 11 5 97.42 3.45
-7 0 -1 0.14 0.44
-7 0 1 0.15 0.38
-7 0 3 0.18 0.51
-7 0 5 -0.16 0.50
-7 0 5 0.45 0.74
-7 0 7 0.33 0.55
-7 0 9 0.10 0.39
-7 0 9 -0.10 0.31
-7 -1 -2 18.34 2.08
-7 -1 0 59.13 3.86
-7 1 0 58.55 3.85
-7 1 2 124.59 5.94
-7 -1 2 113.22 5.73
-7 -1 4 45.94 4.01
-7 1 4 51.96 4.29
-7 -1 6 30.57 2.94
-7 1 6 23.15 3.05
-7 1 6 27.88 2.85
-7 -1 6 20.36 2.87
-7 -1 8 56.89 3.44
-7 1 8 51.61 3.36
-7 -1 10 23.50 1.63
-7 1 10 24.27 1.76
-7 -1 10 21.52 1.65
-7 1 10 23.99 1.74
-7 -2 -1 7.11 1.34
-7 2 1 13.80 1.89
-7 -2 1 12.27 1.84
-7 -2 3 6.52 1.53
-7 2 3 9.23 1.77
-7 2 5 230.87 8.65
-7 -2 5 234.79 9.53
-7 -2 7 319.37 9.21
-7 2 7 303.73 9.41
-7 -2 9 33.33 2.33
-7 2 9 29.04 2.35
-7 2 9 29.44 2.30
-7 -3 0 140.95 6.15
-7 3 0 151.77 6.23
-7 3 2 2.78 0.99
-7 -3 2 1.99 0.89
-7 -3 4 52.98 4.20
-7 3 4 53.93 3.95
-7 -3 6 27.05 3.09
-7 3 6 27.81 2.91
-7 -3 6 25.75 2.40
-7 3 8 3.33 1.07
-7 3 8 1.66 0.77
-7 -3 8 1.48 0.64
-7 -3 10 33.39 2.06
-7 3 10 41.03 2.33
-7 4 1 117.26 5.44
-7 -4 3 123.37 6.23
-7 4 5 28.56 2.96
-7 -4 5 23.17 2.81
-7 -4 7 12.21 1.60
-7 4 7 12.65 1.96
-7 4 9 27.07 2.29
-7 4 9 25.04 2.06
-7 -4 9 29.54 2.12
-7 -4 9 20.80 1.94
-7 5 0 72.18 4.12
-7 -5 4 113.66 6.02
-7 5 4 124.67 6.19
-7 5 6 52.54 3.99
-7 5 8 25.83 2.49
-7 -5 8 29.23 2.28
-7 5 8 31.17 2.85
-7 -5 10 3.16 0.58
-7 -6 -3 2.93 0.92
-7 6 3 19.79 2.34
-7 6 5 29.11 2.98
-7 -6 5 23.79 2.68
-7 -6 7 0.11 0.36
-7 6 7 0.64 0.57
-7 -6 7 0.48 0.63
-7 6 9 27.70 2.14
-7 -6 9 23.34 1.77
-7 -7 -2 11.38 1.75
-7 -7 0 177.61 7.35
-7 7 2 162.16 6.64
-7 7 6 69.17 4.48
-7 -7 8 15.05 1.83
-7 7 8 21.09 2.06
-7 -8 -3 7.06 1.15
-7 -8 -1 17.70 2.14
-7 -8 1 42.21 3.35
-7 8 1 43.97 3.25
-7 8 3 26.61 2.62
-7 8 5 8.77 1.63
-7 8 7 3.94 1.00
-7 -8 7 1.66 0.77
-7 -9 -2 58.11 3.41
-7 -9 0 38.06 3.07
-7 9 2 40.54 3.14
-7 9 6 22.56 2.33
-7 -9 8 50.16 2.75
-7 9 8 64.97 2.98
-7 -10 -1 15.22 1.78
-7 -10 1 18.43 2.08
-7 10 1 21.15 2.13
-7 10 3 57.92 3.63
-7 10 5 12.06 1.69
-7 -10 7 18.49 1.68
-7 -11 -2 39.34 2.32
-7 11 -2 38.35 2.28
-7 -11 0 38.45 2.72
-7 11 0 39.65 2.61
-7 11 2 11.65 1.58
-7 -11 6 4.30 0.88
-7 -12 -1 9.03 1.15
-7 12 -1 8.65 1.07
-7 12 1 2.19 0.67
-7 -12 1 1.85 0.66
-7 12 5 15.90 1.55
-7 -13 0 2.05 0.55
-7 13 0 1.62 0.50
-7 13 2 15.07 1.46
-7 13 4 45.27 2.47
-6 0 0 43.34 3.70
-6 0 2 436.49 11.43
-6 0 2 410.13 12.45
-6 0 4 321.71 9.74
-6 0 4 309.60 10.77
-6 0 6 123.81 6.98
-6 0 6 121.82 6.07
-6 0 8 344.46 10.41
-6 0 8 417.29 9.61
-6 0 10 34.95 2.48
-6 1 -1 58.05 4.40
-6 -1 -1 52.38 4.23
-6 1 1 55.97 4.27
-6 1 1 61.58 4.26
-6 -1 1 55.66 4.12
-6 -1 1 60.36 3.67
-6 1 1 64.71 3.78
-6 1 3 5.61 1.29
-6 -1 3 4.55 1.21
-6 1 3 6.36 1.47
-6 -1 5 108.96 5.49
-6 1 5 115.29 5.72
-6 -1 5 119.18 6.58
-6 1 5 99.87 6.19
-6 -1 7 146.40 5.23
-6 1 7 138.54 6.68
-6 -1 7 121.25 5.57
-6 1 7 117.09 5.72
-6 -1 7 144.20 6.72
-6 1 7 140.40 5.05
-6 -1 9 9.85 1.46
-6 1 9 8.87 1.41
-6 -1 9 7.33 1.36
-6 1 9 11.94 1.35
-6 1 9 8.53 1.45
-6 -1 9 12.84 1.42
-6 -1 9 7.56 1.29
-6 -1 11 49.10 2.38
-6 1 11 46.85 2.40
-6 -2 0 96.32 4.65
-6 -2 0 89.01 5.44
-6 2 2 131.16 5.77
-6 -2 2 131.38 5.82
-6 -2 2 122.71 6.15
-6 2 2 130.53 6.64
-6 2 4 6.37 1.60
-6 -2 4 7.16 1.56
-6 2 4 7.33 1.45
-6 2 4 4.92 1.32
-6 -2 6 53.87 4.43
-6 2 6 52.03 4.02
-6 -2 6 61.79 4.22
-6 2 8 8.56 1.71
-6 -2 8 6.53 1.26
-6 -2 8 8.53 1.47
-6 2 8 5.89 1.35
-6 2 8 10.89 1.38
-6 -2 8 10.07 1.39
-6 -2 10 3.02 0.74
-6 2 10 2.37 0.75
-6 -2 10 3.45 0.77
-6 2 10 3.32 0.68
-6 -2 10 1.07 0.56
-6 -3 -1 1.21 0.76
-6 3 1 41.26 3.74
-6 -3 1 39.88 3.03
-6 -3 1 43.60 3.73
-6 3 3 186.19 6.92
-6 -3 3 191.00 7.59
-6 3 3 200.30 8.43
-6 3 5 82.95 5.02
-6 -3 5 86.83 4.81
-6 -3 5 85.07 5.34
-6 -3 7 2.37 0.84
-6 3 7 2.85 1.12
-6 3 9 0.60 0.57
-6 -3 9 1.11 0.68
-6 -3 9 0.79 0.53
-6 -3 9 1.04 0.54
-6 3 9 1.25 0.52
-6 -4 0 50.38 4.18
-6 4 2 38.79 3.00
-6 -4 2 48.67 3.54
-6 4 2 44.28 3.98
-6 -4 2 42.07 3.66
-6 4 4 26.77 3.03
-6 -4 4 30.06 3.01
-6 4 6 165.28 6.40
-6 4 6 154.58 7.26
-6 -4 6 140.80 5.90
-6 -4 6 153.01 7.26
-6 4 8 18.74 2.40
-6 -4 8 21.58 2.19
-6 4 8 20.24 1.80
-6 4 8 19.36 2.53
-6 -4 10 0.38 0.40
-6 4 10 0.87 0.51
-6 4 10 1.09 0.39
-6 -5 1 258.09 9.82
-6 5 1 258.27 10.08
-6 5 3 562.19 15.62
-6 5 3 520.82 13.19
-6 -5 3 552.88 14.09
-6 5 5 247.54 9.31
-6 -5 5 238.26 9.02
-6 5 7 28.14 3.11
-6 -5 7 33.71 2.76
-6 5 7 31.54 2.75
-6 5 9 60.80 3.99
-6 -5 9 68.71 3.73
-6 6 0 24.99 2.89
-6 6 2 285.50 10.78
-6 6 2 275.56 8.87
-6 6 4 732.91 16.82
-6 -6 4 738.01 17.16
-6 6 4 720.36 18.41
-6 -6 6 263.47 8.27
-6 6 6 281.06 8.60
-6 6 6 282.10 10.34
-6 6 8 72.96 4.71
-6 -6 8 75.12 4.66
-6 6 10 5.87 0.97
-6 -6 10 8.33 1.01
-6 6 10 8.80 0.87
-6 -7 -3 9.88 1.69
-6 7 1 393.88 10.81
-6 7 1 394.52 10.83
-6 7 3 20.44 2.36
-6 7 7 47.41 3.24
-6 -7 7 43.20 3.62
-6 -7 9 7.53 1.07
-6 -7 9 8.34 1.34
-6 7 9 8.17 1.36
-6 -8 -2 100.56 5.39
-6 -8 0 58.68 4.19
-6 8 0 54.50 3.63
-6 8 2 106.65 5.29
-6 8 2 108.62 5.40
-6 8 4 91.24 5.18
-6 8 6 13.60 2.23
-6 8 8 12.32 1.75
-6 -8 8 12.93 1.78
-6 -9 -3 28.11 2.55
-6 -9 -1 60.44 4.17
-6 -9 1 62.99 4.28
-6 9 1 61.16 3.93
-6 9 1 62.33 4.00
-6 9 3 19.99 2.33
-6 -9 7 1.27 0.73
-6 9 7 3.21 0.84
-6 -9 9 7.63 1.07
-6 -10 -2 38.72 3.07
-6 10 0 45.52 3.27
-6 -10 0 50.46 3.74
-6 10 0 47.96 3.38
-6 -10 2 27.46 2.69
-6 10 2 25.26 2.54
-6 10 2 23.56 2.48
-6 10 4 7.91 1.49
-6 -10 6 4.28 1.25
-6 -10 8 8.11 1.12
-6 -10 8 11.26 1.39
-6 11 -1 21.56 2.13
-6 -11 -1 24.94 2.49
-6 -11 1 17.88 2.18
-6 11 1 21.27 2.27
-6 11 1 17.16 2.07
-6 11 3 14.99 1.94
-6 11 5 40.81 3.22
-6 -11 7 43.04 2.71
-6 -12 -2 20.00 1.92
-6 12 -2 19.44 1.92
-6 12 0 21.57 2.11
-6 -12 0 27.35 2.53
-6 12 0 28.31 2.42
-6 12 0 24.01 2.33
-6 12 2 48.18 3.30
-6 -12 2 42.31 3.15
-6 12 4 71.60 3.93
-6 13 -3 24.05 1.71
-6 -13 -1 1.86 0.65
-6 13 -1 2.19 0.65
-6 13 -1 1.99 0.71
-6 13 -1 1.47 0.58
-6 13 1 40.56 2.80
-6 -13 1 45.39 3.07
-6 13 1 48.47 3.06
-6 13 3 37.68 2.70
-6 -13 7 7.54 0.89
-6 14 -2 15.55 1.37
-6 -14 0 9.75 1.30
-6 14 0 10.54 1.29
-6 14 0 11.25 1.38
-6 14 2 10.94 1.36
-6 -14 2 8.97 1.26
-6 -14 6 6.92 0.85
-6 15 1 5.00 0.81
-6 -15 1 6.19 0.92
-5 0 1 0.14 0.31
-5 0 1 1.19 0.57
-5 0 3 1.74 0.75
-5 0 5 1.67 0.75
-5 0 5 -0.14 0.35
-5 0 7 -0.10 0.39
-5 0 7 -0.17 0.42
-5 0 7 0.15 0.41
-5 0 9 0.20 0.41
-5 0 9 -0.13 0.50
-5 0 9 -0.14 0.47
-5 0 11 0.34 0.38
-5 -1 -2 40.27 3.47
-5 -1 0 12.91 1.82
-5 1 0 13.62 1.88
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8 -5 3 4.95 0.87
8 5 3 3.96 0.80
8 6 -8 35.56 1.81
8 6 -6 101.30 4.04
8 6 -4 61.23 3.23
8 -6 -4 51.69 3.31
8 -6 -4 60.71 4.02
8 -6 -2 37.70 2.93
8 -6 -2 41.73 3.34
8 6 -2 38.08 3.13
8 -6 0 62.13 3.57
8 6 0 57.75 3.82
8 -6 0 67.17 3.88
8 6 2 0.93 0.52
8 -6 2 1.17 0.53
8 7 -7 36.88 2.07
8 7 -5 15.53 1.59
8 -7 -5 12.68 1.56
8 7 -3 9.88 1.31
8 -7 -3 13.63 1.71
8 7 -3 9.92 1.57
8 -7 -1 0.47 0.55
8 7 -1 1.25 0.76
8 -7 -1 2.41 0.81
8 7 1 3.81 0.95
8 -7 1 4.48 0.98
8 8 -6 2.64 0.65
8 8 -4 0.35 0.37
8 -8 -4 0.85 0.50
8 8 -4 0.34 0.47
8 -8 -2 15.87 1.78
8 8 -2 14.48 1.83
8 8 0 18.38 1.96
8 -8 0 20.39 2.02
8 8 2 1.86 0.55
8 -8 2 1.56 0.50
8 9 -5 6.41 0.95
8 -9 -5 7.51 1.11
8 -9 -3 5.49 1.03
8 9 -3 4.31 0.97
8 -9 -1 8.63 1.20
8 9 -1 6.92 1.21
8 -9 -1 8.99 1.32
8 9 1 2.28 0.66
8 -9 1 1.98 0.60
8 -10 -4 4.36 0.85
8 10 -4 3.42 0.81
8 -10 -2 0.08 0.31
8 10 -2 0.10 0.37
8 -10 -2 0.37 0.42
8 10 0 10.67 1.27
8 -10 0 14.03 1.45
8 -11 -5 108.56 3.56
8 -11 -3 53.47 2.54
8 -11 -3 50.71 2.71
8 11 -3 54.00 2.78
8 -11 -3 57.44 2.69
8 -11 -1 8.53 0.99
8 11 -1 10.10 1.16
8 -11 -1 10.27 1.15
9 0 -7 -0.05 0.27
9 0 -5 -0.12 0.42
9 0 -3 0.14 0.55
9 0 -1 0.11 0.50
9 1 -6 15.37 1.32
9 1 -4 78.69 4.41
9 -1 -4 76.21 4.27
9 1 -2 44.90 3.20
9 -1 -2 39.30 3.00
9 2 -7 8.26 0.92
9 2 -5 5.07 1.11
9 -2 -5 2.95 0.87
9 -2 -3 7.22 1.22
9 -2 -3 9.36 1.56
9 2 -3 9.30 1.61
9 2 -1 37.80 2.76
9 -2 -1 40.48 2.78
9 2 1 22.07 1.84
9 3 -6 24.71 1.66
9 3 -4 7.36 1.39
9 -3 -4 7.47 1.32
9 -3 -2 25.23 2.16
9 3 -2 29.55 2.55
9 -3 -2 24.52 2.32
9 3 0 -0.10 0.41
9 4 -7 29.78 1.65
9 4 -5 100.12 3.53
9 4 -5 102.40 4.49
9 -4 -5 101.96 4.38
9 -4 -3 22.74 2.00
9 4 -3 22.24 2.34
9 -4 -3 22.72 2.24
9 -4 -1 34.37 2.40
9 4 -1 30.14 2.35
9 4 -1 31.25 2.36
9 4 1 38.72 2.33
9 5 -6 13.43 1.19
9 -5 -4 4.57 0.91
9 5 -4 5.17 1.13
9 -5 -2 62.46 3.26
9 5 -2 66.06 3.63
9 5 0 26.19 2.03
9 6 -5 6.22 0.84
9 6 -5 6.22 1.03
9 -6 -3 2.79 0.73
9 6 -3 4.73 1.05
9 -6 -1 8.09 1.08
9 6 -1 8.27 1.17
9 -7 -4 17.29 1.52
9 7 -4 15.44 1.64
9 -7 -4 16.94 1.49
9 -7 -2 8.75 1.12
9 7 -2 8.15 1.19
9 7 -2 8.28 1.13
9 -7 -2 8.62 1.09
9 -8 -3 3.99 0.74
9 8 -3 5.46 0.93
9 8 -3 4.97 0.82
9 -8 -3 5.26 0.81
10 0 -4 73.65 3.15
10 1 -3 0.42 0.38
10 -1 -3 0.70 0.38
0 0 0 0.00 0.00
TITL exp_329_M-6-2 in Ia
REM Ia (#9 in standard setting)
CELL 1.54184 8.164440 15.923669 9.693553 90.0000 106.6613 90.0000
ZERR 8.00 0.000174 0.000251 0.000199 0.0000 0.0023 0.0000
LATT -2
SYMM x+1/2,-y, z
SFAC C H N O
UNIT 88.00 80.00 8.00 8.00
TREF
HKLF 4
END
_computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)'
;
_shelx_hkl_checksum 11801
_shelx_res_file
;
e329.res created by SHELXL-2014/7
TITL exp_329_m-6-2_a.res in Ia
CELL 1.54184 8.1644 15.9237 9.6936 90 106.661 90
ZERR 4 0.0002 0.0003 0.0002 0 0.002 0
LATT -2
SYMM 0.5+X,-Y,+Z
SFAC C H N O S
UNIT 48 52 12 4 4
EQIV $1 x, 3/2-y, 1/2+z
HTAB N2 N1_$1
HTAB C9 S1
HTAB C12 N1
L.S. 20 0 0
PLAN 10
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
EADP C10 C10B
ACTA
WGHT 0.044800 0.295500
FVAR 0.63256 0.84141
S1 5 0.433143 0.915973 0.555160 11.00000 0.07134 0.03112 =
0.07230 -0.00688 0.03404 0.00246
O1 4 0.933293 0.796902 0.371998 11.00000 0.06269 0.06751 =
0.10372 -0.00863 0.04987 -0.00796
N1 3 0.352200 0.699243 0.394955 11.00000 0.03918 0.03336 =
0.03108 -0.00168 0.01570 -0.00164
N2 3 0.336155 0.727806 0.616942 11.00000 0.04189 0.03807 =
0.02942 -0.00517 0.01509 -0.00546
H2 2 0.349992 0.753588 0.695194 11.00000 0.03787
N3 3 0.658406 0.813950 0.491919 11.00000 0.05238 0.03464 =
0.09184 -0.00912 0.04069 -0.00923
C1 1 0.399203 0.749969 0.507347 11.00000 0.03495 0.03073 =
0.03070 -0.00038 0.01208 -0.00014
C2 1 0.149033 0.605163 0.641790 11.00000 0.05318 0.05670 =
0.04251 0.00302 0.02257 -0.01042
AFIX 43
H2B 2 0.142917 0.616775 0.734208 11.00000 -1.20000
AFIX 0
C3 1 0.067606 0.536626 0.564834 11.00000 0.05166 0.04982 =
0.06447 0.00532 0.02309 -0.01658
AFIX 43
H3A 2 0.004785 0.501182 0.606629 11.00000 -1.20000
AFIX 0
C4 1 0.076708 0.518817 0.425636 11.00000 0.04343 0.04113 =
0.06482 -0.00776 0.01535 -0.00966
AFIX 43
H4A 2 0.020994 0.471601 0.378012 11.00000 -1.20000
AFIX 0
C5 1 0.166297 0.569631 0.357619 11.00000 0.03690 0.04076 =
0.04098 -0.00853 0.01053 -0.00287
AFIX 43
H5A 2 0.170838 0.558127 0.264727 11.00000 -1.20000
AFIX 0
C6 1 0.250250 0.639377 0.434450 11.00000 0.03136 0.03298 =
0.03252 -0.00168 0.01070 0.00125
C7 1 0.240653 0.655872 0.573640 11.00000 0.03511 0.03498 =
0.03295 -0.00025 0.01274 -0.00201
C8 1 0.508290 0.825148 0.515609 11.00000 0.04598 0.03184 =
0.03746 -0.00088 0.01532 -0.00421
PART 1
C9 1 0.777745 0.884049 0.496015 21.00000 0.06609 0.05156 =
0.09427 -0.02057 0.04502 -0.02719
AFIX 23
H9A 2 0.870474 0.882301 0.584790 21.00000 -1.20000
H9B 2 0.718654 0.937269 0.491577 21.00000 -1.20000
AFIX 0
C10 1 0.847323 0.875265 0.368163 21.00000 0.09263 0.05685 =
0.10777 -0.00296 0.06721 -0.01165
AFIX 23
H10A 2 0.754108 0.879046 0.279945 21.00000 -1.20000
H10B 2 0.926274 0.920850 0.368586 21.00000 -1.20000
AFIX 0
C11 1 0.815295 0.729669 0.365806 21.00000 0.04656 0.05210 =
0.06134 -0.00727 0.01708 0.00264
AFIX 23
H11A 2 0.872178 0.676407 0.363685 21.00000 -1.20000
H11B 2 0.721330 0.734258 0.278247 21.00000 -1.20000
AFIX 0
C12 1 0.746809 0.732232 0.494668 21.00000 0.03972 0.04371 =
0.05917 -0.00243 0.01866 0.00138
AFIX 23
H12A 2 0.667464 0.686292 0.490315 21.00000 -1.20000
H12B 2 0.839731 0.726963 0.582807 21.00000 -1.20000
AFIX 0
PART 2
C9B 1 0.715141 0.886947 0.398451 -21.00000 0.08909 0.03020 =
0.10663 0.00889 0.06842 0.00186
AFIX 23
H9C 2 0.668022 0.877962 0.295695 -21.00000 -1.20000
H9D 2 0.684008 0.942456 0.423609 -21.00000 -1.20000
AFIX 0
C10B 1 0.900828 0.873280 0.446885 -21.00000 0.09263 0.05685 =
0.10777 -0.00296 0.06721 -0.01165
AFIX 23
H10C 2 0.939536 0.865381 0.550409 -21.00000 -1.20000
H10D 2 0.960487 0.921060 0.422102 -21.00000 -1.20000
AFIX 0
C11B 1 0.871979 0.731540 0.446230 -21.00000 0.04854 0.06204 =
0.05804 -0.00245 0.01035 0.01536
AFIX 23
H11C 2 0.914103 0.739908 0.549509 -21.00000 -1.20000
H11D 2 0.910983 0.677206 0.423147 -21.00000 -1.20000
AFIX 0
C12B 1 0.688192 0.735272 0.399793 -21.00000 0.05033 0.02858 =
0.07608 0.00232 0.03974 -0.00525
AFIX 23
H12C 2 0.637151 0.684497 0.424347 -21.00000 -1.20000
H12D 2 0.644504 0.745518 0.297117 -21.00000 -1.20000
PART 0
AFIX 0
HKLF 4
REM exp_329_m-6-2_a.res in Ia
REM R1 = 0.0301 for 1692 Fo > 4sig(Fo) and 0.0305 for all 1724 data
REM 189 parameters refined using 2 restraints
END
WGHT 0.0457 0.2860
REM Highest difference peak 0.172, deepest hole -0.191, 1-sigma level 0.048
Q1 1 0.6009 0.8132 0.4017 11.00000 0.05 0.17
Q2 1 0.4847 0.7108 0.7331 11.00000 0.05 0.14
Q3 1 0.4243 0.8794 0.2751 11.00000 0.05 0.13
Q4 1 0.6147 0.8510 0.1275 11.00000 0.05 0.12
Q5 1 1.1183 0.8194 0.6015 11.00000 0.05 0.12
Q6 1 0.6859 0.8648 0.2238 11.00000 0.05 0.12
Q7 1 0.5525 0.9386 0.2286 11.00000 0.05 0.12
Q8 1 0.6618 0.7024 0.2759 11.00000 0.05 0.12
Q9 1 -0.1083 0.4231 0.6744 11.00000 0.05 0.12
Q10 1 0.7996 0.5833 0.2549 11.00000 0.05 0.12
;
_shelx_res_checksum 96052
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.43314(11) 0.91597(4) 0.55516(11) 0.0555(2) Uani d 1 . .
O O1 0.9333(3) 0.79690(17) 0.3720(4) 0.0726(8) Uani d 1 . .
N N1 0.3522(3) 0.69924(13) 0.3950(2) 0.0334(4) Uani d 1 . .
N N2 0.3362(3) 0.72781(14) 0.6169(3) 0.0354(5) Uani d 1 . .
H H2 0.350(4) 0.754(2) 0.695(4) 0.038(8) Uiso d 1 . .
N N3 0.6584(3) 0.81395(16) 0.4919(4) 0.0555(8) Uani d 1 . .
C C1 0.3992(3) 0.74997(16) 0.5073(3) 0.0316(5) Uani d 1 . .
C C2 0.1490(4) 0.6052(2) 0.6418(4) 0.0490(7) Uani d 1 . .
H H2B 0.1429 0.6168 0.7342 0.059 Uiso calc 1 . .
C C3 0.0676(4) 0.5366(2) 0.5648(4) 0.0540(8) Uani d 1 . .
H H3A 0.0048 0.5012 0.6066 0.065 Uiso calc 1 . .
C C4 0.0767(4) 0.51882(19) 0.4256(4) 0.0498(7) Uani d 1 . .
H H4A 0.0210 0.4716 0.3780 0.060 Uiso calc 1 . .
C C5 0.1663(3) 0.56963(17) 0.3576(3) 0.0397(6) Uani d 1 . .
H H5A 0.1708 0.5581 0.2647 0.048 Uiso calc 1 . .
C C6 0.2502(3) 0.63938(15) 0.4345(3) 0.0320(5) Uani d 1 . .
C C7 0.2407(3) 0.65587(16) 0.5736(3) 0.0337(5) Uani d 1 . .
C C8 0.5083(3) 0.82515(16) 0.5156(3) 0.0377(6) Uani d 1 . .
C C9 0.7777(7) 0.8840(3) 0.4960(9) 0.0661(16) Uani d 0.841(11) A 1
H H9A 0.8705 0.8823 0.5848 0.079 Uiso calc 0.841(11) A 1
H H9B 0.7187 0.9373 0.4916 0.079 Uiso calc 0.841(11) A 1
C C10 0.8473(9) 0.8753(4) 0.3682(10) 0.078(2) Uani d 0.841(11) A 1
H H10A 0.7541 0.8790 0.2799 0.093 Uiso calc 0.841(11) A 1
H H10B 0.9263 0.9209 0.3686 0.093 Uiso calc 0.841(11) A 1
C C11 0.8153(7) 0.7297(3) 0.3658(7) 0.0530(12) Uani d 0.841(11) A 1
H H11A 0.8722 0.6764 0.3637 0.064 Uiso calc 0.841(11) A 1
H H11B 0.7213 0.7343 0.2782 0.064 Uiso calc 0.841(11) A 1
C C12 0.7468(6) 0.7322(2) 0.4947(7) 0.0466(11) Uani d 0.841(11) A 1
H H12A 0.6675 0.6863 0.4903 0.056 Uiso calc 0.841(11) A 1
H H12B 0.8397 0.7270 0.5828 0.056 Uiso calc 0.841(11) A 1
C C9B 0.715(5) 0.8869(14) 0.398(5) 0.067(10) Uani d 0.159(11) A 2
H H9C 0.6680 0.8780 0.2957 0.080 Uiso calc 0.159(11) A 2
H H9D 0.6840 0.9425 0.4236 0.080 Uiso calc 0.159(11) A 2
C C10B 0.901(5) 0.873(2) 0.447(5) 0.078(2) Uani d 0.159(11) A 2
H H10C 0.9395 0.8654 0.5504 0.093 Uiso calc 0.159(11) A 2
H H10D 0.9605 0.9211 0.4221 0.093 Uiso calc 0.159(11) A 2
C C11B 0.872(4) 0.7315(17) 0.446(4) 0.057(7) Uani d 0.159(11) A 2
H H11C 0.9141 0.7399 0.5495 0.069 Uiso calc 0.159(11) A 2
H H11D 0.9110 0.6772 0.4231 0.069 Uiso calc 0.159(11) A 2
C C12B 0.688(4) 0.7353(11) 0.400(4) 0.047(7) Uani d 0.159(11) A 2
H H12C 0.6372 0.6845 0.4243 0.057 Uiso calc 0.159(11) A 2
H H12D 0.6445 0.7455 0.2971 0.057 Uiso calc 0.159(11) A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0713(5) 0.0311(3) 0.0723(5) 0.0025(3) 0.0340(4) -0.0069(4)
O1 0.0627(14) 0.0675(16) 0.104(2) -0.0080(12) 0.0499(15) -0.0086(15)
N1 0.0392(10) 0.0334(10) 0.0311(11) -0.0016(8) 0.0157(9) -0.0017(8)
N2 0.0419(12) 0.0381(11) 0.0294(12) -0.0055(9) 0.0151(9) -0.0052(10)
N3 0.0524(15) 0.0346(13) 0.092(2) -0.0092(10) 0.0407(16) -0.0091(13)
C1 0.0349(13) 0.0307(11) 0.0307(12) -0.0001(9) 0.0121(10) -0.0004(9)
C2 0.0532(17) 0.0567(16) 0.0425(16) -0.0104(14) 0.0226(14) 0.0030(14)
C3 0.0517(17) 0.0498(16) 0.064(2) -0.0166(14) 0.0231(16) 0.0053(15)
C4 0.0434(15) 0.0411(15) 0.065(2) -0.0097(11) 0.0154(14) -0.0078(14)
C5 0.0369(12) 0.0408(13) 0.0410(15) -0.0029(10) 0.0105(11) -0.0085(12)
C6 0.0314(11) 0.0330(11) 0.0325(12) 0.0012(9) 0.0107(10) -0.0017(10)
C7 0.0351(11) 0.0350(11) 0.0329(13) -0.0020(10) 0.0127(10) -0.0002(10)
C8 0.0460(14) 0.0318(12) 0.0375(14) -0.0042(10) 0.0153(12) -0.0009(10)
C9 0.066(3) 0.052(2) 0.094(5) -0.027(2) 0.045(3) -0.021(3)
C10 0.093(4) 0.057(2) 0.108(5) -0.012(3) 0.067(5) -0.003(4)
C11 0.047(3) 0.052(2) 0.061(3) 0.0026(18) 0.017(2) -0.007(2)
C12 0.0397(19) 0.0437(19) 0.059(3) 0.0014(16) 0.019(2) -0.0024(19)
C9B 0.09(2) 0.030(9) 0.11(3) 0.002(11) 0.07(2) 0.009(14)
C10B 0.093(4) 0.057(2) 0.108(5) -0.012(3) 0.067(5) -0.003(4)
C11B 0.049(14) 0.062(14) 0.058(17) 0.015(10) 0.010(12) -0.002(13)
C12B 0.050(13) 0.029(8) 0.08(2) -0.005(8) 0.040(14) 0.002(10)
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'
O O 0.0492 0.0322 '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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 O1 C11 . . 109.5(4) ?
C11B O1 C10B . . 102(2) ?
C1 N1 C6 . . 104.3(2) ?
C1 N2 C7 . . 106.6(2) ?
C1 N2 H2 . . 127(2) ?
C7 N2 H2 . . 127(2) ?
C8 N3 C9 . . 122.1(3) ?
C8 N3 C12 . . 125.8(3) ?
C9 N3 C12 . . 110.4(3) ?
C8 N3 C12B . . 120.0(9) ?
C8 N3 C9B . . 115.3(10) ?
C12B N3 C9B . . 97.8(16) ?
N1 C1 N2 . . 113.7(2) ?
N1 C1 C8 . . 124.5(2) ?
N2 C1 C8 . . 121.8(2) ?
C3 C2 C7 . . 116.4(3) ?
C3 C2 H2B . . 121.8 ?
C7 C2 H2B . . 121.8 ?
C2 C3 C4 . . 122.0(3) ?
C2 C3 H3A . . 119.0 ?
C4 C3 H3A . . 119.0 ?
C5 C4 C3 . . 121.6(3) ?
C5 C4 H4A . . 119.2 ?
C3 C4 H4A . . 119.2 ?
C4 C5 C6 . . 117.2(3) ?
C4 C5 H5A . . 121.4 ?
C6 C5 H5A . . 121.4 ?
N1 C6 C7 . . 109.9(2) ?
N1 C6 C5 . . 129.6(2) ?
C7 C6 C5 . . 120.5(2) ?
N2 C7 C2 . . 132.2(3) ?
N2 C7 C6 . . 105.4(2) ?
C2 C7 C6 . . 122.4(2) ?
N3 C8 C1 . . 117.1(2) ?
N3 C8 S1 . . 125.5(2) ?
C1 C8 S1 . . 117.5(2) ?
N3 C9 C10 . . 108.0(5) ?
N3 C9 H9A . . 110.1 ?
C10 C9 H9A . . 110.1 ?
N3 C9 H9B . . 110.1 ?
C10 C9 H9B . . 110.1 ?
H9A C9 H9B . . 108.4 ?
O1 C10 C9 . . 110.9(6) ?
O1 C10 H10A . . 109.5 ?
C9 C10 H10A . . 109.5 ?
O1 C10 H10B . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 108.0 ?
O1 C11 C12 . . 110.5(4) ?
O1 C11 H11A . . 109.5 ?
C12 C11 H11A . . 109.5 ?
O1 C11 H11B . . 109.5 ?
C12 C11 H11B . . 109.5 ?
H11A C11 H11B . . 108.1 ?
N3 C12 C11 . . 107.6(4) ?
N3 C12 H12A . . 110.2 ?
C11 C12 H12A . . 110.2 ?
N3 C12 H12B . . 110.2 ?
C11 C12 H12B . . 110.2 ?
H12A C12 H12B . . 108.5 ?
C10B C9B N3 . . 99(3) ?
C10B C9B H9C . . 112.1 ?
N3 C9B H9C . . 112.1 ?
C10B C9B H9D . . 112.1 ?
N3 C9B H9D . . 112.1 ?
H9C C9B H9D . . 109.7 ?
C9B C10B O1 . . 106(3) ?
C9B C10B H10C . . 110.5 ?
O1 C10B H10C . . 110.5 ?
C9B C10B H10D . . 110.5 ?
O1 C10B H10D . . 110.5 ?
H10C C10B H10D . . 108.7 ?
O1 C11B C12B . . 107(2) ?
O1 C11B H11C . . 110.3 ?
C12B C11B H11C . . 110.3 ?
O1 C11B H11D . . 110.3 ?
C12B C11B H11D . . 110.3 ?
H11C C11B H11D . . 108.5 ?
C11B C12B N3 . . 100(3) ?
C11B C12B H12C . . 111.8 ?
N3 C12B H12C . . 111.8 ?
C11B C12B H12D . . 111.8 ?
N3 C12B H12D . . 111.8 ?
H12C C12B H12D . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 . 1.658(3) ?
O1 C10 . 1.427(7) ?
O1 C11 . 1.430(5) ?
O1 C11B . 1.43(3) ?
O1 C10B . 1.48(4) ?
N1 C1 . 1.322(3) ?
N1 C6 . 1.390(3) ?
N2 C1 . 1.353(3) ?
N2 C7 . 1.382(3) ?
N2 H2 . 0.84(4) ?
N3 C8 . 1.322(3) ?
N3 C9 . 1.475(5) ?
N3 C12 . 1.485(5) ?
N3 C12B . 1.60(2) ?
N3 C9B . 1.62(2) ?
C1 C8 . 1.480(3) ?
C2 C3 . 1.380(5) ?
C2 C7 . 1.390(4) ?
C2 H2B . 0.9300 ?
C3 C4 . 1.401(5) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.379(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.402(3) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.399(4) ?
C9 C10 . 1.511(10) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.508(8) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C9B C10B . 1.47(6) ?
C9B H9C . 0.9700 ?
C9B H9D . 0.9700 ?
C10B H10C . 0.9700 ?
C10B H10D . 0.9700 ?
C11B C12B . 1.44(4) ?
C11B H11C . 0.9700 ?
C11B H11D . 0.9700 ?
C12B H12C . 0.9700 ?
C12B H12D . 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2 N1 4_465 0.84(4) 2.07(4) 2.903(3) 169(3) yes
C9 H9B S1 . 0.97 2.60 3.070(5) 110.1 yes
C12 H12A N1 . 0.97 2.48 3.131(5) 124.2 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C1 N2 . . . . 0.1(3) ?
C6 N1 C1 C8 . . . . -179.1(2) ?
C7 N2 C1 N1 . . . . 0.6(3) ?
C7 N2 C1 C8 . . . . 179.8(2) ?
C7 C2 C3 C4 . . . . 0.1(5) ?
C2 C3 C4 C5 . . . . -0.7(5) ?
C3 C4 C5 C6 . . . . 0.9(4) ?
C1 N1 C6 C7 . . . . -0.7(3) ?
C1 N1 C6 C5 . . . . -179.5(3) ?
C4 C5 C6 N1 . . . . 178.1(3) ?
C4 C5 C6 C7 . . . . -0.5(4) ?
C1 N2 C7 C2 . . . . 179.1(3) ?
C1 N2 C7 C6 . . . . -1.0(3) ?
C3 C2 C7 N2 . . . . -179.8(3) ?
C3 C2 C7 C6 . . . . 0.3(5) ?
N1 C6 C7 N2 . . . . 1.1(3) ?
C5 C6 C7 N2 . . . . 180.0(2) ?
N1 C6 C7 C2 . . . . -179.0(3) ?
C5 C6 C7 C2 . . . . -0.1(4) ?
C9 N3 C8 C1 . . . . 179.5(5) ?
C12 N3 C8 C1 . . . . -16.6(5) ?
C12B N3 C8 C1 . . . . 23.7(15) ?
C9B N3 C8 C1 . . . . 140.3(19) ?
C9 N3 C8 S1 . . . . -1.1(6) ?
C12 N3 C8 S1 . . . . 162.8(4) ?
C12B N3 C8 S1 . . . . -156.9(15) ?
C9B N3 C8 S1 . . . . -40.3(19) ?
N1 C1 C8 N3 . . . . -55.2(4) ?
N2 C1 C8 N3 . . . . 125.7(3) ?
N1 C1 C8 S1 . . . . 125.4(2) ?
N2 C1 C8 S1 . . . . -53.7(3) ?
C8 N3 C9 C10 . . . . -135.7(5) ?
C12 N3 C9 C10 . . . . 58.2(9) ?
C11 O1 C10 C9 . . . . 61.3(8) ?
N3 C9 C10 O1 . . . . -59.2(9) ?
C10 O1 C11 C12 . . . . -62.0(8) ?
C8 N3 C12 C11 . . . . 135.6(4) ?
C9 N3 C12 C11 . . . . -58.9(7) ?
O1 C11 C12 N3 . . . . 60.2(6) ?
C8 N3 C9B C10B . . . . 157(2) ?
C12B N3 C9B C10B . . . . -74(3) ?
N3 C9B C10B O1 . . . . 76(3) ?
C11B O1 C10B C9B . . . . -73(4) ?
C10B O1 C11B C12B . . . . 74(4) ?
O1 C11B C12B N3 . . . . -77(3) ?
C8 N3 C12B C11B . . . . -160.0(16) ?
C9B N3 C12B C11B . . . . 75(3) ?
_cod_database_fobs_code 2244161