#------------------------------------------------------------------------------
#$Date: 2022-05-05 02:36:13 +0200 (Thu 05 de May de 2022) $
#$Revision: 274903 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/86/7158665.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_7158665
loop_
_publ_author_name
'Mikshiev, Vladimir Y.'
'Tolstoy, Peter'
'Puzyk, Aleksandra M.'
'Kirichenko, Sergey O.'
'Antonov, Alexander S.'
_publ_section_title
;
 peri-Interactions in 1,8-bis(dimethylamino)naphthalene ortho-ketimine
 cations facilitate [1,5]-hydride shift: selective synthesis of
 1,2,3,4-tetrahydrobenzo[h]quinazolines
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00674J
_journal_year                    2022
_chemical_formula_moiety         'C25 H25 N3'
_chemical_formula_sum            'C25 H25 N3'
_chemical_formula_weight         367.48
_chemical_name_systematic
N,N,1-trimethyl-4-(naphthalen-1-yl)-1,2,3,4-tetrahydrobenzo[h]quinazolin-10-amine
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc29hy0s
_audit_creation_date             2021-12-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-12-22 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                72.713(2)
_cell_angle_beta                 89.359(2)
_cell_angle_gamma                80.928(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9740(3)
_cell_length_b                   10.1567(3)
_cell_length_c                   11.2275(3)
_cell_measurement_reflns_used    8061
_cell_measurement_temperature    99.8(9)
_cell_measurement_theta_max      78.1100
_cell_measurement_theta_min      4.1410
_cell_volume                     964.20(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00 119.00   0.50    0.18    --   47.10  57.00 -30.00  170
  2  ω     86.00 159.00   0.50    0.80    --  113.25 103.00 -80.00  146
  3  ω    100.00 177.00   0.50    0.80    --  113.25  61.00 -30.00  154
  4  ω    130.00 168.00   0.50    0.80    --  113.25  45.00   0.00   76
  5  ω    102.00 173.00   0.50    0.80    --  113.25  15.00  90.00  142
  6  ω   -104.00 -33.00   0.50    0.80    -- -106.00  77.00 120.00  142
  7  ω    -71.00 -39.00   0.50    0.80    -- -106.00  61.00  60.00   64
  8  ω    -68.00 -43.00   0.50    0.80    -- -106.00  61.00  90.00   50
  9  ω    -80.00 -34.00   0.50    0.80    -- -106.00 125.00 120.00   92
 10  ω   -108.00 -82.00   0.50    0.80    -- -106.00 125.00 120.00   52
 11  ω   -112.00 -86.00   0.50    0.80    -- -106.00 125.00  60.00   52
 12  ω    -61.00 -36.00   0.50    0.80    -- -106.00 125.00  60.00   50
 13  ω    -58.00 -33.00   0.50    0.80    -- -106.00 110.00  21.40   50
 14  ω   -108.00 -73.00   0.50    0.80    -- -106.00 110.00  21.40   70
 15  ω   -106.00 -64.00   0.50    0.80    -- -106.00 108.00 119.29   84
 16  ω   -112.00 -38.00   0.50    0.80    -- -106.00 125.00 -60.00  148
 17  ω   -109.00 -82.00   0.50    0.80    -- -106.00 125.00 -90.00   54
 18  ω    -67.00 -35.00   0.50    0.80    -- -106.00 125.00 -90.00   64
 19  ω    -61.00 -36.00   0.50    0.80    -- -106.00 106.00-159.81   50
 20  ω   -107.00 -81.00   0.50    0.80    -- -106.00 106.00-159.81   52
 21  ω   -106.00 -73.00   0.50    0.80    -- -106.00 103.00 -80.00   66
 22  ω    -64.00 -24.00   0.50    0.18    --  -47.10 103.00 -80.00   80
 23  ω   -154.00 -93.00   0.50    0.80    -- -106.00 -30.00-120.00  122
 24  ω   -174.00-119.00   0.50    0.80    -- -106.00 -45.00-150.00  110
 25  ω   -175.00-120.00   0.50    0.80    -- -106.00 -45.00 -60.00  110
 26  ω   -140.00 -85.00   0.50    0.80    -- -106.00-103.00 176.00  110
 27  ω   -105.00 -78.00   0.50    0.18    --  -47.10-125.00 -30.00   54
 28  ω   -114.00 -73.00   0.50    0.18    --  -47.10-125.00 -60.00   82
 29  ω    -22.00  25.00   0.50    0.18    --   47.10 -19.00  90.00   94
 30  ω     42.00  67.00   0.50    0.80    --  113.25 -61.00  60.00   50
 31  ω     43.00  69.00   0.50    0.80    --  113.25 -61.00   0.00   52
 32  ω     43.00  70.00   0.50    0.80    --  113.25 -61.00 -30.00   54
 33  ω    -24.00  62.00   0.50    0.18    --   47.10 -57.00-150.00  172
 34  ω     45.00 105.00   0.50    0.80    --  113.25 -77.00-180.00  120
 35  ω     46.00  71.00   0.50    0.80    --  113.25 -61.00-150.00   50
 36  ω     48.00  92.00   0.50    0.18    --   47.10-125.00-180.00   88
 37  ω     43.00 108.00   0.50    0.80    --  113.25-125.00 -60.00  130
 38  ω     43.00  82.00   0.50    0.80    --  113.25-125.00 -30.00   78
 39  ω     48.00  77.00   0.50    0.80    --  113.25 -94.00-180.00   58
 40  ω     52.00 105.00   0.50    0.80    --  113.25 -94.00   0.00  106
 41  ω     79.00 106.00   0.50    0.80    --  113.25 -94.00-180.00   54
 42  ω     70.00 108.00   0.50    0.80    --  113.25-111.00  16.51   76
 43  ω     -5.00  81.00   0.50    0.18    --   47.10-103.00 176.00  172
 44  ω     53.00  79.00   0.50    0.80    --  113.25-103.00 176.00   52
 45  ω     62.00 102.00   0.50    0.80    --  113.25 -94.00 120.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0658300000
_diffrn_orient_matrix_UB_12      -0.0772107000
_diffrn_orient_matrix_UB_13      -0.0927306000
_diffrn_orient_matrix_UB_21      -0.1142470000
_diffrn_orient_matrix_UB_22      0.0970646000
_diffrn_orient_matrix_UB_23      -0.1021161000
_diffrn_orient_matrix_UB_31      0.1134861000
_diffrn_orient_matrix_UB_32      0.1026123000
_diffrn_orient_matrix_UB_33      -0.0406702000
_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  0.0314
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11725
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.996
_diffrn_reflns_theta_min         4.127
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3647
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0420
_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/[σ²(Fo²)+(0.0668P)²+0.2484P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1199
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3214
_reflns_number_total             3647
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00674j2.cif
_cod_data_source_block           20081_lja-7
_cod_database_code               7158665
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C25 H25 N3'
_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   0.955
_shelx_estimated_absorpt_t_min   0.934
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C16(H16), C21(H21), C9(H9), C5(H5), C15(H15), C6(H6), C18(H18),
 C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C24(H24A,H24B,H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.459
_oxdiff_exptl_absorpt_empirical_full_min 0.784
loop_
_space_group_symop_operation_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_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
N2 N 0.59916(11) 0.15591(11) 0.67851(10) 0.0196(2) Uani 1 1 d . . . . .
N3 N 0.46331(12) -0.06871(11) 0.80314(10) 0.0221(2) Uani 1 1 d . . . . .
N1 N 0.71088(12) 0.35781(11) 0.58177(10) 0.0231(3) Uani 1 1 d . . . . .
H1 H 0.799(2) 0.3914(17) 0.5589(15) 0.028 Uiso 1 1 d . U . . .
C11 C 0.47675(13) 0.38118(13) 0.69232(11) 0.0192(3) Uani 1 1 d . . . . .
C13 C 0.69122(13) 0.50046(12) 0.73143(11) 0.0196(3) Uani 1 1 d . . . . .
C22 C 0.78743(13) 0.60378(12) 0.68652(12) 0.0199(3) Uani 1 1 d . . . . .
C3 C 0.34469(13) 0.17906(12) 0.76686(11) 0.0182(3) Uani 1 1 d . . . . .
C4 C 0.33588(14) 0.03113(13) 0.80539(11) 0.0205(3) Uani 1 1 d . . . . .
C17 C 0.86185(14) 0.65039(13) 0.77463(12) 0.0210(3) Uani 1 1 d . . . . .
C8 C 0.21523(14) 0.27192(13) 0.78465(11) 0.0206(3) Uani 1 1 d . . . . .
C2 C 0.47430(13) 0.23985(12) 0.71201(11) 0.0180(3) Uani 1 1 d . . . . .
C10 C 0.34931(14) 0.46805(13) 0.71818(12) 0.0216(3) Uani 1 1 d . . . . .
H10 H 0.3533 0.5639 0.7067 0.026 Uiso 1 1 calc R U . . .
C7 C 0.07882(14) 0.22208(14) 0.82650(12) 0.0240(3) Uani 1 1 d . . . . .
C1 C 0.73523(14) 0.21716(13) 0.66862(12) 0.0224(3) Uani 1 1 d . . . . .
H1A H 0.8175 0.1584 0.6394 0.027 Uiso 1 1 calc R U . . .
H1B H 0.7665 0.2204 0.7518 0.027 Uiso 1 1 calc R U . . .
C16 C 0.84041(14) 0.59288(13) 0.90399(12) 0.0234(3) Uani 1 1 d . . . . .
H16 H 0.8891 0.6241 0.9628 0.028 Uiso 1 1 calc R U . . .
C21 C 0.81137(14) 0.66457(13) 0.55740(12) 0.0231(3) Uani 1 1 d . . . . .
H21 H 0.7625 0.6358 0.4970 0.028 Uiso 1 1 calc R U . . .
C14 C 0.67583(14) 0.44744(13) 0.85768(12) 0.0221(3) Uani 1 1 d . . . . .
C12 C 0.60984(14) 0.45119(13) 0.63703(11) 0.0202(3) Uani 1 1 d . . . . .
H12 H 0.5686 0.5363 0.5673 0.024 Uiso 1 1 calc R U . . .
C9 C 0.22133(14) 0.41645(13) 0.75915(12) 0.0225(3) Uani 1 1 d . . . . .
H9 H 0.1348 0.4777 0.7709 0.027 Uiso 1 1 calc R U . . .
C5 C 0.19947(15) -0.01123(14) 0.84412(12) 0.0245(3) Uani 1 1 d . . . . .
H5 H 0.1928 -0.1079 0.8659 0.029 Uiso 1 1 calc R U . . .
C15 C 0.75057(15) 0.49338(14) 0.94450(12) 0.0248(3) Uani 1 1 d . . . . .
H15 H 0.7380 0.4547 1.0314 0.030 Uiso 1 1 calc R U . . .
C6 C 0.07088(15) 0.08337(14) 0.85237(12) 0.0262(3) Uani 1 1 d . . . . .
H6 H -0.0219 0.0509 0.8760 0.031 Uiso 1 1 calc R U . . .
C18 C 0.95583(15) 0.75312(13) 0.73141(13) 0.0254(3) Uani 1 1 d . . . . .
H18 H 1.0049 0.7844 0.7900 0.030 Uiso 1 1 calc R U . . .
C23 C 0.57049(15) 0.10894(14) 0.57065(12) 0.0247(3) Uani 1 1 d . . . . .
H23A H 0.4697 0.0826 0.5752 0.037 Uiso 1 1 calc R U . . .
H23B H 0.6464 0.0280 0.5711 0.037 Uiso 1 1 calc R U . . .
H23C H 0.5763 0.1848 0.4936 0.037 Uiso 1 1 calc R U . . .
C19 C 0.97716(15) 0.80818(14) 0.60659(14) 0.0280(3) Uani 1 1 d . . . . .
H19 H 1.0415 0.8763 0.5792 0.034 Uiso 1 1 calc R U . . .
C25 C 0.43648(17) -0.20421(13) 0.79807(13) 0.0287(3) Uani 1 1 d . . . . .
H25A H 0.4058 -0.2578 0.8799 0.043 Uiso 1 1 calc R U . . .
H25B H 0.5293 -0.2550 0.7756 0.043 Uiso 1 1 calc R U . . .
H25C H 0.3562 -0.1914 0.7353 0.043 Uiso 1 1 calc R U . . .
C24 C 0.58944(15) -0.08286(14) 0.88988(13) 0.0270(3) Uani 1 1 d . . . . .
H24A H 0.5938 0.0078 0.9027 0.041 Uiso 1 1 calc R U . . .
H24B H 0.6841 -0.1148 0.8551 0.041 Uiso 1 1 calc R U . . .
H24C H 0.5749 -0.1511 0.9699 0.041 Uiso 1 1 calc R U . . .
C20 C 0.90328(15) 0.76358(14) 0.51866(13) 0.0274(3) Uani 1 1 d . . . . .
H20 H 0.9175 0.8025 0.4321 0.033 Uiso 1 1 calc R U . . .
H14 H 0.6070(16) 0.3799(15) 0.8896(14) 0.017(3) Uiso 1 1 d . . . . .
H7 H -0.0133(19) 0.2893(18) 0.8392(16) 0.031(4) Uiso 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'
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
C2 N2 C1 112.35(9) . . ?
C2 N2 C23 114.79(10) . . ?
C1 N2 C23 112.72(10) . . ?
C4 N3 C25 117.33(10) . . ?
C4 N3 C24 116.76(10) . . ?
C25 N3 C24 111.24(11) . . ?
C1 N1 H1 112.9(11) . . ?
C1 N1 C12 109.28(10) . . ?
C12 N1 H1 111.0(10) . . ?
C2 C11 C10 120.28(11) . . ?
C2 C11 C12 122.77(11) . . ?
C10 C11 C12 116.88(11) . . ?
C22 C13 C12 119.10(11) . . ?
C14 C13 C22 119.08(11) . . ?
C14 C13 C12 121.81(11) . . ?
C17 C22 C13 118.94(11) . . ?
C21 C22 C13 123.31(11) . . ?
C21 C22 C17 117.74(11) . . ?
C8 C3 C4 117.28(11) . . ?
C8 C3 C2 117.57(11) . . ?
C2 C3 C4 125.15(11) . . ?
N3 C4 C3 120.95(11) . . ?
C5 C4 N3 120.11(11) . . ?
C5 C4 C3 118.94(12) . . ?
C16 C17 C22 119.47(11) . . ?
C18 C17 C22 119.45(12) . . ?
C18 C17 C16 121.08(11) . . ?
C7 C8 C3 120.91(11) . . ?
C9 C8 C3 119.99(11) . . ?
C9 C8 C7 119.09(12) . . ?
N2 C2 C3 120.34(10) . . ?
C11 C2 N2 119.64(11) . . ?
C11 C2 C3 120.02(11) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 C11 120.92(11) . . ?
C9 C10 H10 119.5 . . ?
C8 C7 H7 120.4(9) . . ?
C6 C7 C8 120.03(12) . . ?
C6 C7 H7 119.6(9) . . ?
N2 C1 N1 110.71(10) . . ?
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
C17 C16 H16 119.7 . . ?
C15 C16 C17 120.55(11) . . ?
C15 C16 H16 119.7 . . ?
C22 C21 H21 119.3 . . ?
C20 C21 C22 121.36(12) . . ?
C20 C21 H21 119.3 . . ?
C13 C14 C15 121.70(11) . . ?
C13 C14 H14 120.0(9) . . ?
C15 C14 H14 118.2(9) . . ?
N1 C12 C11 109.47(10) . . ?
N1 C12 C13 113.25(10) . . ?
N1 C12 H12 107.1 . . ?
C11 C12 C13 112.37(10) . . ?
C11 C12 H12 107.1 . . ?
C13 C12 H12 107.1 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.77(12) . . ?
C10 C9 H9 119.6 . . ?
C4 C5 H5 118.8 . . ?
C4 C5 C6 122.34(12) . . ?
C6 C5 H5 118.8 . . ?
C16 C15 C14 120.24(12) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C7 C6 C5 120.08(12) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C17 C18 H18 119.4 . . ?
C19 C18 C17 121.11(12) . . ?
C19 C18 H18 119.4 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.90(12) . . ?
C20 C19 H19 120.1 . . ?
N3 C25 H25A 109.5 . . ?
N3 C25 H25B 109.5 . . ?
N3 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
N3 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C20 C19 120.43(12) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
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
N2 C2 1.4155(16) . ?
N2 C1 1.4442(15) . ?
N2 C23 1.4661(15) . ?
N3 C4 1.4090(16) . ?
N3 C25 1.4514(16) . ?
N3 C24 1.4630(17) . ?
N1 H1 0.911(18) . ?
N1 C1 1.4552(17) . ?
N1 C12 1.4740(16) . ?
C11 C2 1.3897(17) . ?
C11 C10 1.4132(18) . ?
C11 C12 1.5186(16) . ?
C13 C22 1.4362(17) . ?
C13 C14 1.3725(18) . ?
C13 C12 1.5345(16) . ?
C22 C17 1.4288(17) . ?
C22 C21 1.4254(18) . ?
C3 C4 1.4496(17) . ?
C3 C8 1.4285(18) . ?
C3 C2 1.4484(17) . ?
C4 C5 1.3842(18) . ?
C17 C16 1.4187(18) . ?
C17 C18 1.4152(18) . ?
C8 C7 1.4201(18) . ?
C8 C9 1.4194(18) . ?
C10 H10 0.9500 . ?
C10 C9 1.3564(18) . ?
C7 C6 1.3646(19) . ?
C7 H7 1.023(17) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C16 H16 0.9500 . ?
C16 C15 1.3615(19) . ?
C21 H21 0.9500 . ?
C21 C20 1.3690(18) . ?
C14 C15 1.4148(18) . ?
C14 H14 0.982(15) . ?
C12 H12 1.0000 . ?
C9 H9 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.4016(19) . ?
C15 H15 0.9500 . ?
C6 H6 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.369(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C19 H19 0.9500 . ?
C19 C20 1.4122(19) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C20 H20 0.9500 . ?
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
N3 C4 C5 C6 177.64(11) . . . . ?
C11 C10 C9 C8 4.00(19) . . . . ?
C13 C22 C17 C16 0.62(17) . . . . ?
C13 C22 C17 C18 -179.42(11) . . . . ?
C13 C22 C21 C20 179.52(12) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C22 C13 C14 C15 0.91(18) . . . . ?
C22 C13 C12 N1 74.11(14) . . . . ?
C22 C13 C12 C11 -161.20(11) . . . . ?
C22 C17 C16 C15 0.43(19) . . . . ?
C22 C17 C18 C19 -0.29(19) . . . . ?
C22 C21 C20 C19 0.0(2) . . . . ?
C3 C4 C5 C6 -2.70(18) . . . . ?
C3 C8 C7 C6 1.13(19) . . . . ?
C3 C8 C9 C10 -0.19(18) . . . . ?
C4 C3 C8 C7 -6.23(17) . . . . ?
C4 C3 C8 C9 174.45(11) . . . . ?
C4 C3 C2 N2 7.46(17) . . . . ?
C4 C3 C2 C11 -172.36(11) . . . . ?
C4 C5 C6 C7 -2.6(2) . . . . ?
C17 C22 C21 C20 0.45(19) . . . . ?
C17 C16 C15 C14 -0.8(2) . . . . ?
C17 C18 C19 C20 0.7(2) . . . . ?
C8 C3 C4 N3 -173.43(10) . . . . ?
C8 C3 C4 C5 6.92(17) . . . . ?
C8 C3 C2 N2 -172.62(10) . . . . ?
C8 C3 C2 C11 7.55(16) . . . . ?
C8 C7 C6 C5 3.41(19) . . . . ?
C2 N2 C1 N1 -55.27(13) . . . . ?
C2 C11 C10 C9 -1.85(18) . . . . ?
C2 C11 C12 N1 13.84(16) . . . . ?
C2 C11 C12 C13 -112.91(13) . . . . ?
C2 C3 C4 N3 6.49(18) . . . . ?
C2 C3 C4 C5 -173.17(11) . . . . ?
C2 C3 C8 C7 173.85(11) . . . . ?
C2 C3 C8 C9 -5.47(17) . . . . ?
C10 C11 C2 N2 176.13(10) . . . . ?
C10 C11 C2 C3 -4.05(17) . . . . ?
C10 C11 C12 N1 -163.14(10) . . . . ?
C10 C11 C12 C13 70.12(14) . . . . ?
C7 C8 C9 C10 -179.53(11) . . . . ?
C1 N2 C2 C11 20.72(15) . . . . ?
C1 N2 C2 C3 -159.10(11) . . . . ?
C1 N1 C12 C11 -45.98(13) . . . . ?
C1 N1 C12 C13 80.26(12) . . . . ?
C16 C17 C18 C19 179.68(12) . . . . ?
C21 C22 C17 C16 179.73(11) . . . . ?
C21 C22 C17 C18 -0.30(18) . . . . ?
C14 C13 C22 C17 -1.27(17) . . . . ?
C14 C13 C22 C21 179.67(11) . . . . ?
C14 C13 C12 N1 -105.20(13) . . . . ?
C14 C13 C12 C11 19.48(16) . . . . ?
C12 N1 C1 N2 69.83(12) . . . . ?
C12 C11 C2 N2 -0.74(17) . . . . ?
C12 C11 C2 C3 179.08(10) . . . . ?
C12 C11 C10 C9 175.21(11) . . . . ?
C12 C13 C22 C17 179.40(10) . . . . ?
C12 C13 C22 C21 0.34(18) . . . . ?
C12 C13 C14 C15 -179.78(12) . . . . ?
C9 C8 C7 C6 -179.54(12) . . . . ?
C18 C17 C16 C15 -179.54(12) . . . . ?
C18 C19 C20 C21 -0.6(2) . . . . ?
C23 N2 C2 C11 -109.82(12) . . . . ?
C23 N2 C2 C3 70.36(14) . . . . ?
C23 N2 C1 N1 76.32(13) . . . . ?
C25 N3 C4 C3 -158.07(11) . . . . ?
C25 N3 C4 C5 21.58(17) . . . . ?
C24 N3 C4 C3 66.08(15) . . . . ?
C24 N3 C4 C5 -114.27(13) . . . . ?
