#------------------------------------------------------------------------------
#$Date: 2020-02-14 02:29:37 +0200 (Fri, 14 Feb 2020) $
#$Revision: 248141 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/79/4037926.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_4037926
loop_
_publ_author_name
'Chen, Yang'
'Li, Siqi'
'Hou, Shili'
'Xu, Jiaxi'
'Yang, Zhanhui'
_publ_section_title
;
 Chiral Synthesis of McGeachin-Type Bisaminals.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03362
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C24 H25 N3'
_chemical_formula_sum            'C24 H25 N3'
_chemical_formula_weight         355.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-05-18
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.231(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9702(3)
_cell_length_b                   9.4474(3)
_cell_length_c                   12.8774(4)
_cell_measurement_reflns_used    3972
_cell_measurement_temperature    109.85(10)
_cell_measurement_theta_max      71.0070
_cell_measurement_theta_min      3.4680
_cell_volume                     957.08(6)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      109.85(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9984
_diffrn_measured_fraction_theta_max 0.9924
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -29.00    9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -57.0000   60.0000 38

#__ type_ start__ end____ width___ exp.time_
  2 omega   18.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -57.0000   60.0000 36

#__ type_ start__ end____ width___ exp.time_
  3 omega   44.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000   90.0000 31

#__ type_ start__ end____ width___ exp.time_
  4 omega   15.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega   83.00  108.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega   92.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   73.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 34

#__ type_ start__ end____ width___ exp.time_
  8 omega   54.00  121.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   30.0000 67

#__ type_ start__ end____ width___ exp.time_
  9 omega  100.00  125.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 10 omega   68.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 47

#__ type_ start__ end____ width___ exp.time_
 11 omega   50.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 57

#__ type_ start__ end____ width___ exp.time_
 12 omega   42.00  142.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000    0.0000 100

#__ type_ start__ end____ width___ exp.time_
 13 omega   67.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   57.0000 -120.0000 37

#__ type_ start__ end____ width___ exp.time_
 14 omega   49.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000 -180.0000 54

#__ type_ start__ end____ width___ exp.time_
 15 omega   36.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   57.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 16 omega   22.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   57.0000    0.0000 81

#__ type_ start__ end____ width___ exp.time_
 17 omega   38.00   76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 38

#__ type_ start__ end____ width___ exp.time_
 18 omega   44.00   71.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 19 omega   43.00   71.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 28

#__ type_ start__ end____ width___ exp.time_
 20 omega   39.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 50

#__ type_ start__ end____ width___ exp.time_
 21 omega   44.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 47

#__ type_ start__ end____ width___ exp.time_
 22 omega   56.00   99.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 43

#__ type_ start__ end____ width___ exp.time_
 23 omega   44.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 24 omega    0.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega  -30.00   -4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   47.00   95.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 48

#__ type_ start__ end____ width___ exp.time_
 27 omega   46.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 28 omega   42.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000   90.0000 133

#__ type_ start__ end____ width___ exp.time_
 29 omega   58.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000  -60.0000 51

#__ type_ start__ end____ width___ exp.time_
 30 omega   21.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   57.0000  150.0000 76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0831771000
_diffrn_orient_matrix_UB_12      0.1292383000
_diffrn_orient_matrix_UB_13      0.0442618000
_diffrn_orient_matrix_UB_21      -0.0794872000
_diffrn_orient_matrix_UB_22      -0.0977678000
_diffrn_orient_matrix_UB_23      0.0746377000
_diffrn_orient_matrix_UB_31      0.1585203000
_diffrn_orient_matrix_UB_32      0.0186928000
_diffrn_orient_matrix_UB_33      0.0846073000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6036
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.901
_diffrn_reflns_theta_min         5.624
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.563
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74599
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       Block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1563 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(19)
_refine_ls_extinction_coef       0.0147(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3588
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0323
_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)+(0.0523P)²+0.1301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0863
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                3524
_reflns_number_total             3588
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03362_si_002.cif
_cod_data_source_block           exp_5470
_cod_original_cell_volume        957.07(6)
_cod_database_code               4037926
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelx_estimated_absorpt_t_max   0.872
_shelx_estimated_absorpt_t_min   0.806
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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 0.3079(2) 0.85229(18) 0.22130(12) 0.0186(3) Uani 1 1 d . . . . .
C9 C 0.1237(3) 0.6009(2) 0.15173(16) 0.0201(4) Uani 1 1 d . . . . .
H9 H 0.0155 0.5706 0.1104 0.024 Uiso 1 1 calc R U . . .
N1 N 0.0850(2) 0.68642(17) 0.24013(12) 0.0179(3) Uani 1 1 d . . . . .
C11 C 0.3043(2) 0.8135(2) 0.11768(15) 0.0179(4) Uani 1 1 d . . . . .
C12 C 0.3776(2) 0.8985(2) 0.04681(16) 0.0228(4) Uani 1 1 d . . . . .
H12 H 0.4321 0.9824 0.0701 0.027 Uiso 1 1 calc R U . . .
N3 N 0.2143(2) 0.47492(18) 0.19421(14) 0.0259(4) Uani 1 1 d . . . . .
C22 C 0.5024(2) 0.6488(2) 0.40764(15) 0.0209(4) Uani 1 1 d . . . . .
H22 H 0.5131 0.7358 0.4418 0.025 Uiso 1 1 calc R U . . .
C2 C -0.0674(2) 0.8916(2) 0.29693(15) 0.0195(4) Uani 1 1 d . . . . .
C17 C 0.3702(2) 0.6285(2) 0.32456(14) 0.0192(4) Uani 1 1 d . . . . .
C3 C -0.1279(2) 0.8418(2) 0.38591(16) 0.0247(4) Uani 1 1 d . . . . .
H3 H -0.1537 0.7463 0.3911 0.030 Uiso 1 1 calc R U . . .
C16 C 0.2456(2) 0.7480(2) 0.29075(14) 0.0173(4) Uani 1 1 d . . . . .
H16 H 0.2245 0.7975 0.3543 0.021 Uiso 1 1 calc R U . . .
C14 C 0.2890(3) 0.7334(3) -0.09418(16) 0.0286(5) Uani 1 1 d . . . . .
H14 H 0.2861 0.7056 -0.1637 0.034 Uiso 1 1 calc R U . . .
C23 C 0.4171(3) 0.9654(2) 0.26794(16) 0.0232(4) Uani 1 1 d . . . . .
H23A H 0.5337 0.9401 0.2677 0.035 Uiso 1 1 calc R U . . .
H23B H 0.3990 0.9805 0.3390 0.035 Uiso 1 1 calc R U . . .
H23C H 0.3910 1.0507 0.2280 0.035 Uiso 1 1 calc R U . . .
C18 C 0.3514(3) 0.4956(2) 0.27401(15) 0.0201(4) Uani 1 1 d . . . . .
C21 C 0.6189(3) 0.5426(2) 0.44092(16) 0.0262(5) Uani 1 1 d . . . . .
H21 H 0.7075 0.5583 0.4961 0.031 Uiso 1 1 calc R U . . .
C1 C -0.0489(2) 0.7930(2) 0.20635(15) 0.0199(4) Uani 1 1 d . . . . .
H1 H -0.0155 0.8491 0.1490 0.024 Uiso 1 1 calc R U . . .
C15 C 0.2134(3) 0.6508(2) -0.02537(16) 0.0250(4) Uani 1 1 d . . . . .
H15 H 0.1578 0.5679 -0.0501 0.030 Uiso 1 1 calc R U . . .
C10 C 0.2187(2) 0.6887(2) 0.07956(15) 0.0197(4) Uani 1 1 d . . . . .
C4 C -0.1500(3) 0.9336(3) 0.46706(17) 0.0296(5) Uani 1 1 d . . . . .
H4 H -0.1912 0.8994 0.5258 0.036 Uiso 1 1 calc R U . . .
C6 C -0.0499(3) 1.1261(2) 0.37307(18) 0.0296(5) Uani 1 1 d . . . . .
H6 H -0.0236 1.2216 0.3684 0.035 Uiso 1 1 calc R U . . .
C13 C 0.3688(3) 0.8578(3) -0.05738(16) 0.0277(5) Uani 1 1 d . . . . .
H13 H 0.4173 0.9150 -0.1033 0.033 Uiso 1 1 calc R U . . .
C5 C -0.1111(3) 1.0756(3) 0.46063(18) 0.0309(5) Uani 1 1 d . . . . .
H5 H -0.1260 1.1369 0.5149 0.037 Uiso 1 1 calc R U . . .
C24 C 0.1931(3) 0.3456(3) 0.1346(2) 0.0347(5) Uani 1 1 d . . . . .
H24A H 0.0842 0.3459 0.0901 0.052 Uiso 1 1 calc R U . . .
H24B H 0.1999 0.2665 0.1818 0.052 Uiso 1 1 calc R U . . .
H24C H 0.2811 0.3382 0.0919 0.052 Uiso 1 1 calc R U . . .
C7 C -0.0277(2) 1.0342(2) 0.29213(16) 0.0228(4) Uani 1 1 d . . . . .
H7 H 0.0145 1.0688 0.2338 0.027 Uiso 1 1 calc R U . . .
C19 C 0.4685(3) 0.3885(2) 0.30835(17) 0.0253(4) Uani 1 1 d . . . . .
H19 H 0.4574 0.3003 0.2758 0.030 Uiso 1 1 calc R U . . .
C20 C 0.6009(3) 0.4125(2) 0.39035(17) 0.0275(5) Uani 1 1 d . . . . .
H20 H 0.6784 0.3406 0.4117 0.033 Uiso 1 1 calc R U . . .
C8 C -0.2189(3) 0.7199(3) 0.16594(18) 0.0308(5) Uani 1 1 d . . . . .
H8A H -0.2107 0.6702 0.1019 0.046 Uiso 1 1 calc R U . . .
H8B H -0.3072 0.7898 0.1528 0.046 Uiso 1 1 calc R U . . .
H8C H -0.2450 0.6541 0.2179 0.046 Uiso 1 1 calc R U . . .
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
C11 N2 C16 117.01(16) . . ?
C11 N2 C23 121.01(16) . . ?
C23 N2 C16 118.83(15) . . ?
N1 C9 H9 107.8 . . ?
N1 C9 C10 110.98(16) . . ?
N3 C9 H9 107.8 . . ?
N3 C9 N1 108.19(16) . . ?
N3 C9 C10 114.03(17) . . ?
C10 C9 H9 107.8 . . ?
C9 N1 C1 112.16(15) . . ?
C16 N1 C9 106.69(15) . . ?
C16 N1 C1 113.50(15) . . ?
N2 C11 C12 121.89(18) . . ?
N2 C11 C10 119.48(17) . . ?
C12 C11 C10 118.57(17) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C18 N3 C9 116.63(16) . . ?
C18 N3 C24 121.70(18) . . ?
C24 N3 C9 119.08(17) . . ?
C17 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C21 C22 C17 121.7(2) . . ?
C3 C2 C1 120.92(19) . . ?
C7 C2 C3 118.39(19) . . ?
C7 C2 C1 120.68(18) . . ?
C22 C17 C16 119.90(18) . . ?
C22 C17 C18 119.25(18) . . ?
C18 C17 C16 120.84(17) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
N2 C16 C17 113.77(15) . . ?
N2 C16 H16 107.9 . . ?
N1 C16 N2 110.66(15) . . ?
N1 C16 C17 108.52(16) . . ?
N1 C16 H16 107.9 . . ?
C17 C16 H16 107.9 . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.79(19) . . ?
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 . . ?
N3 C18 C17 118.60(17) . . ?
N3 C18 C19 122.56(18) . . ?
C19 C18 C17 118.81(18) . . ?
C22 C21 H21 120.6 . . ?
C22 C21 C20 118.81(19) . . ?
C20 C21 H21 120.6 . . ?
N1 C1 C2 110.23(15) . . ?
N1 C1 H1 108.6 . . ?
N1 C1 C8 110.42(17) . . ?
C2 C1 H1 108.6 . . ?
C2 C1 C8 110.28(16) . . ?
C8 C1 H1 108.6 . . ?
C14 C15 H15 119.1 . . ?
C14 C15 C10 121.7(2) . . ?
C10 C15 H15 119.1 . . ?
C11 C10 C9 119.98(16) . . ?
C15 C10 C9 120.55(19) . . ?
C15 C10 C11 119.37(19) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0(2) . . ?
C7 C6 H6 120.0 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.09(19) . . ?
C14 C13 H13 119.5 . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
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 . . ?
C2 C7 C6 121.1(2) . . ?
C2 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.7(2) . . ?
C20 C19 H19 119.7 . . ?
C21 C20 H20 119.6 . . ?
C19 C20 C21 120.74(19) . . ?
C19 C20 H20 119.6 . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
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
N2 C11 1.380(2) . ?
N2 C16 1.470(2) . ?
N2 C23 1.447(2) . ?
C9 H9 0.9800 . ?
C9 N1 1.468(2) . ?
C9 N3 1.453(3) . ?
C9 C10 1.533(3) . ?
N1 C16 1.460(2) . ?
N1 C1 1.481(2) . ?
C11 C12 1.410(3) . ?
C11 C10 1.411(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.387(3) . ?
N3 C18 1.389(3) . ?
N3 C24 1.438(3) . ?
C22 H22 0.9300 . ?
C22 C17 1.389(3) . ?
C22 C21 1.387(3) . ?
C2 C3 1.394(3) . ?
C2 C1 1.518(3) . ?
C2 C7 1.388(3) . ?
C17 C16 1.520(3) . ?
C17 C18 1.412(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(3) . ?
C16 H16 0.9800 . ?
C14 H14 0.9300 . ?
C14 C15 1.389(3) . ?
C14 C13 1.383(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C18 C19 1.399(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.388(3) . ?
C1 H1 0.9800 . ?
C1 C8 1.535(3) . ?
C15 H15 0.9300 . ?
C15 C10 1.392(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.384(3) . ?
C6 C7 1.390(3) . ?
C13 H13 0.9300 . ?
C5 H5 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C7 H7 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.386(3) . ?
C20 H20 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
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
N2 C11 C12 C13 -178.70(17) . . . . ?
N2 C11 C10 C9 2.8(3) . . . . ?
N2 C11 C10 C15 179.17(18) . . . . ?
C9 N1 C16 N2 67.86(18) . . . . ?
C9 N1 C16 C17 -57.63(18) . . . . ?
C9 N1 C1 C2 -172.27(15) . . . . ?
C9 N1 C1 C8 65.6(2) . . . . ?
C9 N3 C18 C17 14.3(3) . . . . ?
C9 N3 C18 C19 -167.74(18) . . . . ?
N1 C9 N3 C18 -49.4(2) . . . . ?
N1 C9 N3 C24 148.54(19) . . . . ?
N1 C9 C10 C11 20.3(2) . . . . ?
N1 C9 C10 C15 -156.04(17) . . . . ?
C11 N2 C16 N1 -46.1(2) . . . . ?
C11 N2 C16 C17 76.4(2) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C11 C10 C9 -174.41(17) . . . . ?
C12 C11 C10 C15 2.0(3) . . . . ?
N3 C9 N1 C16 72.18(19) . . . . ?
N3 C9 N1 C1 -162.95(15) . . . . ?
N3 C9 C10 C11 -102.2(2) . . . . ?
N3 C9 C10 C15 81.5(2) . . . . ?
N3 C18 C19 C20 -178.12(19) . . . . ?
C22 C17 C16 N2 81.8(2) . . . . ?
C22 C17 C16 N1 -154.55(16) . . . . ?
C22 C17 C18 N3 177.15(17) . . . . ?
C22 C17 C18 C19 -0.9(3) . . . . ?
C22 C21 C20 C19 -0.3(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C17 C22 C21 C20 -0.8(3) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C3 C2 C1 N1 -66.5(2) . . . . ?
C3 C2 C1 C8 55.7(2) . . . . ?
C3 C2 C7 C6 -1.0(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C16 N2 C11 C12 -173.03(16) . . . . ?
C16 N2 C11 C10 9.9(2) . . . . ?
C16 N1 C1 C2 -51.3(2) . . . . ?
C16 N1 C1 C8 -173.35(16) . . . . ?
C16 C17 C18 N3 -1.5(3) . . . . ?
C16 C17 C18 C19 -179.53(17) . . . . ?
C14 C15 C10 C9 175.75(18) . . . . ?
C14 C15 C10 C11 -0.6(3) . . . . ?
C23 N2 C11 C12 -13.3(3) . . . . ?
C23 N2 C11 C10 169.58(17) . . . . ?
C23 N2 C16 N1 153.74(16) . . . . ?
C23 N2 C16 C17 -83.8(2) . . . . ?
C18 C17 C16 N2 -99.6(2) . . . . ?
C18 C17 C16 N1 24.1(2) . . . . ?
C18 C19 C20 C21 0.8(3) . . . . ?
C21 C22 C17 C16 -179.96(17) . . . . ?
C21 C22 C17 C18 1.4(3) . . . . ?
C1 N1 C16 N2 -56.2(2) . . . . ?
C1 N1 C16 C17 178.33(14) . . . . ?
C1 C2 C3 C4 -177.82(17) . . . . ?
C1 C2 C7 C6 177.75(17) . . . . ?
C15 C14 C13 C12 1.6(3) . . . . ?
C10 C9 N1 C16 -53.63(19) . . . . ?
C10 C9 N1 C1 71.2(2) . . . . ?
C10 C9 N3 C18 74.6(2) . . . . ?
C10 C9 N3 C24 -87.5(2) . . . . ?
C10 C11 C12 C13 -1.6(3) . . . . ?
C13 C14 C15 C10 -1.2(3) . . . . ?
C5 C6 C7 C2 0.6(3) . . . . ?
C24 N3 C18 C17 175.9(2) . . . . ?
C24 N3 C18 C19 -6.2(3) . . . . ?
C7 C2 C3 C4 0.9(3) . . . . ?
C7 C2 C1 N1 114.76(19) . . . . ?
C7 C2 C1 C8 -123.1(2) . . . . ?
C7 C6 C5 C4 0.0(3) . . . . ?
