#------------------------------------------------------------------------------
#$Date: 2024-07-05 20:56:51 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293253 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159960.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_7159960
loop_
_publ_author_name
'Chen, Jia-Zhen'
'Wang, Zhong-Xia'
_publ_section_title
;
 Ruthenium-catalyzed C-H functionalization of indoles and indolines with
 7-azabenzonorbornadienes: access to aminodihydronaphthyl indoles and
 indolines.
;
_journal_issue                   25
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5159
_journal_page_last               5169
_journal_paper_doi               10.1039/d4ob00678j
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C26 H29 N3 O3'
_chemical_formula_sum            'C26 H29 N3 O3'
_chemical_formula_weight         431.52
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2023-12-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-04-26 deposited with the CCDC.	2024-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   24.63533(17)
_cell_length_b                   24.63533(17)
_cell_length_c                   20.65170(17)
_cell_measurement_reflns_used    24547
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.6770
_cell_measurement_theta_min      4.6440
_cell_volume                     10854.33(14)
_computing_cell_refinement       'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    2.00    --  -41.51 -38.00-180.00   99
  2  ω    -82.00  39.00   1.00    2.00    --  -41.51  19.00  90.00  121
  3  ω      6.00  81.00   1.00    2.00    --   41.51 -99.00 120.00   75
  4  ω     58.00 129.00   1.00    2.00    --   41.51-178.00 150.00   71
  5  ω     61.00 130.00   1.00    2.00    --   41.51 178.00 -90.00   69
  6  ω     35.00 113.00   1.00    4.00    --  105.74-125.00   0.00   78
  7  ω     23.00 107.00   1.00    4.00    --  105.74 -94.00 -90.00   84
  8  ω    103.00 178.00   1.00    4.00    --  105.74  77.00  60.00   75
  9  ω    103.00 178.00   1.00    4.00    --  105.74  77.00  30.00   75
 10  ω     77.00 178.00   1.00    4.00    --  105.74  61.00 -90.00  101
 11  ω     97.00 177.00   1.00    4.00    --  105.74 125.00 -30.00   80
 12  ω     23.00 107.00   1.00    4.00    --  105.74 -94.00 120.00   84
 13  ω     53.00 178.00   1.00    4.00    --  105.74  15.00 150.00  125
 14  ω   -114.00 -13.00   1.00    2.00    --  -41.51 -57.00 -90.00  101
 15  ω   -114.00 -13.00   1.00    2.00    --  -41.51 -57.00   0.00  101
 16  ω   -114.00 -13.00   1.00    2.00    --  -41.51 -57.00  90.00  101
 17  ω     77.00 144.00   1.00    4.00    --  105.74  61.00-150.00   67
 18  ω     77.00 178.00   1.00    4.00    --  105.74  30.00   0.00  101
 19  ω    103.00 178.00   1.00    4.00    --  105.74  77.00-180.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0147237000
_diffrn_orient_matrix_UB_12      -0.0421697000
_diffrn_orient_matrix_UB_13      -0.0600827000
_diffrn_orient_matrix_UB_21      0.0139380000
_diffrn_orient_matrix_UB_22      -0.0448950000
_diffrn_orient_matrix_UB_23      0.0391049000
_diffrn_orient_matrix_UB_31      -0.0693028000
_diffrn_orient_matrix_UB_32      -0.0376964000
_diffrn_orient_matrix_UB_33      0.0206300000
_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  0.0262
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            36158
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.777
_diffrn_reflns_theta_min         3.588
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_description       block
_exptl_crystal_F_000             4140
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.00097(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4802
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0394
_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)+(0.0556P)²+5.8661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1102
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4487
_reflns_number_total             4802
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00678j2.cif
_cod_data_source_block           cjz-20231124_auto
_cod_depositor_comments
'Adding full bibliography for 7159960--7159961.cif.'
_cod_original_cell_volume        10854.33(18)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               7159960
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         C20H20N2O2
_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   0.912
_shelx_estimated_absorpt_t_min   0.869
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C10(H10), C9(H9)
1.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C18(H18), C7(H7), C13(H13), C14(H14), C15(H15), C3(H3A), C16(H16),
 C17(H17), C6(H6), C2(H2), C1(H1)
1.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C24(H24A,H24B,H24C), C20(H20A,H20B,H20C), C25(H25A,H25B,
 H25C), C21(H21A,H21B,H21C)
;
_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 1.264
_oxdiff_exptl_absorpt_empirical_full_min 0.820
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
O2 O 0.77728(4) 0.59114(4) 0.63748(4) 0.0538(2) Uani 1 1 d . . . . .
O3 O 0.70548(4) 0.52667(4) 0.71165(5) 0.0555(2) Uani 1 1 d . . . . .
O1 O 0.75630(5) 0.70613(5) 0.45306(5) 0.0679(3) Uani 1 1 d . . . . .
N3 N 0.70162(4) 0.60896(4) 0.67787(5) 0.0433(2) Uani 1 1 d . . . . .
H3 H 0.6720 0.5967 0.7060 0.052 Uiso 1 1 calc R U . . .
N1 N 0.73153(5) 0.61024(4) 0.49397(5) 0.0465(2) Uani 1 1 d . . . . .
N2 N 0.83413(5) 0.68344(5) 0.46482(5) 0.0576(3) Uani 1 1 d . . . . .
C22 C 0.73245(5) 0.57704(5) 0.67196(5) 0.0422(2) Uani 1 1 d . . . . .
C10 C 0.71681(5) 0.66345(5) 0.63829(5) 0.0414(2) Uani 1 1 d . . . . .
H10 H 0.7614 0.6840 0.6270 0.050 Uiso 1 1 calc R U . . .
C11 C 0.70558(6) 0.70886(5) 0.67775(6) 0.0471(3) Uani 1 1 d . . . . .
C19 C 0.77473(6) 0.67048(6) 0.46944(5) 0.0482(3) Uani 1 1 d . . . . .
C9 C 0.67799(6) 0.64609(6) 0.57466(6) 0.0466(3) Uani 1 1 d . . . . .
H9 H 0.6958 0.6839 0.5477 0.056 Uiso 1 1 calc R U . . .
C8 C 0.68206(6) 0.59653(6) 0.53666(6) 0.0465(3) Uani 1 1 d . . . . .
C23 C 0.72661(6) 0.48102(5) 0.71263(6) 0.0489(3) Uani 1 1 d . . . . .
C12 C 0.64596(7) 0.70310(6) 0.67683(6) 0.0553(3) Uani 1 1 d . . . . .
C18 C 0.75196(7) 0.75314(6) 0.71723(6) 0.0592(3) Uani 1 1 d . . . . .
H18 H 0.7910 0.7559 0.7190 0.071 Uiso 1 1 calc R U . . .
C4 C 0.72212(6) 0.55403(6) 0.46743(6) 0.0539(3) Uani 1 1 d . . . . .
C7 C 0.64426(6) 0.53351(6) 0.53932(7) 0.0569(3) Uani 1 1 d . . . . .
H7 H 0.6089 0.5122 0.5652 0.068 Uiso 1 1 calc R U . . .
C5 C 0.66787(7) 0.50539(6) 0.49568(7) 0.0596(3) Uani 1 1 d . . . . .
C13 C 0.59739(7) 0.65565(7) 0.63603(7) 0.0642(4) Uani 1 1 d . . . . .
H13 H 0.5558 0.6445 0.6431 0.077 Uiso 1 1 calc R U . . .
C14 C 0.61102(6) 0.62800(7) 0.58894(7) 0.0607(3) Uani 1 1 d . . . . .
H14 H 0.5788 0.5970 0.5643 0.073 Uiso 1 1 calc R U . . .
C15 C 0.63530(9) 0.74343(8) 0.71537(8) 0.0728(5) Uani 1 1 d . . . . .
H15 H 0.5959 0.7398 0.7157 0.087 Uiso 1 1 calc R U . . .
C26 C 0.79242(6) 0.51039(7) 0.73912(8) 0.0646(4) Uani 1 1 d . . . . .
H26A H 0.8208 0.5427 0.7102 0.097 Uiso 1 1 calc R U . . .
H26B H 0.8043 0.4789 0.7432 0.097 Uiso 1 1 calc R U . . .
H26C H 0.7940 0.5283 0.7809 0.097 Uiso 1 1 calc R U . . .
C24 C 0.68105(7) 0.43295(7) 0.76040(9) 0.0684(4) Uani 1 1 d . . . . .
H24A H 0.6833 0.4531 0.8009 0.103 Uiso 1 1 calc R U . . .
H24B H 0.6919 0.4009 0.7671 0.103 Uiso 1 1 calc R U . . .
H24C H 0.6392 0.4144 0.7435 0.103 Uiso 1 1 calc R U . . .
C3 C 0.75502(9) 0.54343(8) 0.41917(8) 0.0724(4) Uani 1 1 d . . . . .
H3A H 0.7904 0.5763 0.4002 0.087 Uiso 1 1 calc R U . . .
C20 C 0.86164(7) 0.65359(8) 0.50317(8) 0.0687(4) Uani 1 1 d . . . . .
H20A H 0.8970 0.6850 0.5268 0.103 Uiso 1 1 calc R U . . .
H20B H 0.8750 0.6315 0.4750 0.103 Uiso 1 1 calc R U . . .
H20C H 0.8310 0.6246 0.5330 0.103 Uiso 1 1 calc R U . . .
C25 C 0.72055(10) 0.45291(8) 0.64625(8) 0.0795(5) Uani 1 1 d . . . . .
H25A H 0.6788 0.4378 0.6302 0.119 Uiso 1 1 calc R U . . .
H25B H 0.7288 0.4188 0.6490 0.119 Uiso 1 1 calc R U . . .
H25C H 0.7502 0.4843 0.6174 0.119 Uiso 1 1 calc R U . . .
C16 C 0.68239(11) 0.78831(9) 0.75284(8) 0.0842(5) Uani 1 1 d . . . . .
H16 H 0.6749 0.8155 0.7775 0.101 Uiso 1 1 calc R U . . .
C17 C 0.74050(10) 0.79341(8) 0.75423(8) 0.0780(5) Uani 1 1 d . . . . .
H17 H 0.7721 0.8238 0.7799 0.094 Uiso 1 1 calc R U . . .
C6 C 0.64696(9) 0.44368(7) 0.47582(10) 0.0839(5) Uani 1 1 d . . . . .
H6 H 0.6114 0.4104 0.4942 0.101 Uiso 1 1 calc R U . . .
C21 C 0.87799(9) 0.73881(8) 0.42813(9) 0.0855(5) Uani 1 1 d . . . . .
H21A H 0.8556 0.7563 0.4069 0.128 Uiso 1 1 calc R U . . .
H21B H 0.8988 0.7272 0.3963 0.128 Uiso 1 1 calc R U . . .
H21C H 0.9085 0.7693 0.4570 0.128 Uiso 1 1 calc R U . . .
C2 C 0.73307(11) 0.48214(10) 0.40058(11) 0.0952(6) Uani 1 1 d . . . . .
H2 H 0.7543 0.4735 0.3686 0.114 Uiso 1 1 calc R U . . .
C1 C 0.68013(12) 0.43339(9) 0.42859(12) 0.1003(7) Uani 1 1 d . . . . .
H1 H 0.6666 0.3926 0.4151 0.120 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'
O O 0.0492 0.0322 '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
C22 O3 C23 121.04(9) . . ?
C22 N3 H3 119.0 . . ?
C22 N3 C10 121.99(9) . . ?
C10 N3 H3 119.0 . . ?
C8 N1 C19 125.71(10) . . ?
C4 N1 C19 124.26(10) . . ?
C4 N1 C8 108.34(10) . . ?
C19 N2 C20 124.79(11) . . ?
C19 N2 C21 118.11(13) . . ?
C20 N2 C21 116.10(13) . . ?
O2 C22 O3 125.41(10) . . ?
O2 C22 N3 125.96(10) . . ?
N3 C22 O3 108.63(9) . . ?
N3 C10 H10 108.5 . . ?
N3 C10 C11 108.76(8) . . ?
N3 C10 C9 112.52(9) . . ?
C11 C10 H10 108.5 . . ?
C11 C10 C9 110.05(9) . . ?
C9 C10 H10 108.5 . . ?
C12 C11 C10 119.06(11) . . ?
C18 C11 C10 120.98(11) . . ?
C18 C11 C12 119.85(12) . . ?
O1 C19 N1 119.82(12) . . ?
O1 C19 N2 124.41(12) . . ?
N2 C19 N1 115.75(10) . . ?
C10 C9 H9 107.3 . . ?
C8 C9 C10 112.63(9) . . ?
C8 C9 H9 107.3 . . ?
C8 C9 C14 111.80(11) . . ?
C14 C9 C10 110.36(10) . . ?
C14 C9 H9 107.3 . . ?
N1 C8 C9 122.56(10) . . ?
C7 C8 N1 108.56(11) . . ?
C7 C8 C9 128.74(12) . . ?
O3 C23 C26 110.34(11) . . ?
O3 C23 C24 101.60(10) . . ?
O3 C23 C25 110.50(11) . . ?
C26 C23 C24 109.65(11) . . ?
C25 C23 C26 112.66(13) . . ?
C25 C23 C24 111.55(12) . . ?
C11 C12 C13 119.25(11) . . ?
C15 C12 C11 118.68(15) . . ?
C15 C12 C13 122.07(14) . . ?
C11 C18 H18 119.8 . . ?
C11 C18 C17 120.33(15) . . ?
C17 C18 H18 119.8 . . ?
N1 C4 C5 107.41(12) . . ?
C3 C4 N1 130.14(14) . . ?
C3 C4 C5 122.34(13) . . ?
C8 C7 H7 125.7 . . ?
C8 C7 C5 108.52(12) . . ?
C5 C7 H7 125.7 . . ?
C4 C5 C7 107.11(11) . . ?
C4 C5 C6 118.85(15) . . ?
C6 C5 C7 133.98(16) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.45(13) . . ?
C14 C13 H13 119.3 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.90(14) . . ?
C13 C14 H14 119.6 . . ?
C12 C15 H15 119.7 . . ?
C16 C15 C12 120.70(16) . . ?
C16 C15 H15 119.7 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C4 C3 H3A 121.3 . . ?
C2 C3 C4 117.33(18) . . ?
C2 C3 H3A 121.3 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.53(14) . . ?
C17 C16 H16 119.7 . . ?
C18 C17 H17 120.1 . . ?
C16 C17 C18 119.87(17) . . ?
C16 C17 H17 120.1 . . ?
C5 C6 H6 120.7 . . ?
C1 C6 C5 118.55(18) . . ?
C1 C6 H6 120.7 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C3 C2 H2 119.4 . . ?
C3 C2 C1 121.16(18) . . ?
C1 C2 H2 119.4 . . ?
C6 C1 C2 121.74(16) . . ?
C6 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
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
O2 C22 1.2098(13) . ?
O3 C22 1.3524(13) . ?
O3 C23 1.4565(13) . ?
O1 C19 1.2208(15) . ?
N3 H3 0.8600 . ?
N3 C22 1.3443(14) . ?
N3 C10 1.4519(13) . ?
N1 C19 1.4187(15) . ?
N1 C8 1.4019(15) . ?
N1 C4 1.3965(15) . ?
N2 C19 1.3361(17) . ?
N2 C20 1.4579(19) . ?
N2 C21 1.4590(18) . ?
C10 H10 0.9800 . ?
C10 C11 1.5173(15) . ?
C10 C9 1.5542(16) . ?
C11 C12 1.4032(18) . ?
C11 C18 1.383(2) . ?
C9 H9 0.9800 . ?
C9 C8 1.4964(16) . ?
C9 C14 1.5073(17) . ?
C8 C7 1.3545(18) . ?
C23 C26 1.5095(18) . ?
C23 C24 1.5186(17) . ?
C23 C25 1.509(2) . ?
C12 C13 1.452(2) . ?
C12 C15 1.3966(19) . ?
C18 H18 0.9300 . ?
C18 C17 1.388(2) . ?
C4 C5 1.400(2) . ?
C4 C3 1.389(2) . ?
C7 H7 0.9300 . ?
C7 C5 1.426(2) . ?
C5 C6 1.400(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.323(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.373(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C3 H3A 0.9300 . ?
C3 C2 1.380(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C16 H16 0.9300 . ?
C16 C17 1.373(3) . ?
C17 H17 0.9300 . ?
C6 H6 0.9300 . ?
C6 C1 1.375(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C2 H2 0.9300 . ?
C2 C1 1.383(3) . ?
C1 H1 0.9300 . ?
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
N3 H3 O1 0.86 2.05 2.8965(13) 168.0 6_565
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 C10 C11 C12 -88.95(12) . . . . ?
N3 C10 C11 C18 87.25(13) . . . . ?
N3 C10 C9 C8 -52.83(12) . . . . ?
N3 C10 C9 C14 72.88(12) . . . . ?
N1 C8 C7 C5 -2.33(14) . . . . ?
N1 C4 C5 C7 0.69(14) . . . . ?
N1 C4 C5 C6 178.26(13) . . . . ?
N1 C4 C3 C2 -177.17(15) . . . . ?
C22 O3 C23 C26 66.79(15) . . . . ?
C22 O3 C23 C24 -176.97(11) . . . . ?
C22 O3 C23 C25 -58.47(16) . . . . ?
C22 N3 C10 C11 -147.12(11) . . . . ?
C22 N3 C10 C9 90.68(13) . . . . ?
C10 N3 C22 O2 4.77(19) . . . . ?
C10 N3 C22 O3 -175.95(10) . . . . ?
C10 C11 C12 C13 -2.65(16) . . . . ?
C10 C11 C12 C15 177.39(10) . . . . ?
C10 C11 C18 C17 -178.47(12) . . . . ?
C10 C9 C8 N1 -83.88(13) . . . . ?
C10 C9 C8 C7 91.27(15) . . . . ?
C10 C9 C14 C13 34.63(17) . . . . ?
C11 C10 C9 C8 -174.31(9) . . . . ?
C11 C10 C9 C14 -48.59(12) . . . . ?
C11 C12 C13 C14 -16.12(19) . . . . ?
C11 C12 C15 C16 0.7(2) . . . . ?
C11 C18 C17 C16 1.6(2) . . . . ?
C19 N1 C8 C9 -15.58(17) . . . . ?
C19 N1 C8 C7 168.40(11) . . . . ?
C19 N1 C4 C5 -167.98(11) . . . . ?
C19 N1 C4 C3 8.2(2) . . . . ?
C9 C10 C11 C12 34.73(13) . . . . ?
C9 C10 C11 C18 -149.07(11) . . . . ?
C9 C8 C7 C5 -178.03(11) . . . . ?
C8 N1 C19 O1 -40.72(17) . . . . ?
C8 N1 C19 N2 140.61(12) . . . . ?
C8 N1 C4 C5 -2.11(13) . . . . ?
C8 N1 C4 C3 174.05(14) . . . . ?
C8 C9 C14 C13 160.82(12) . . . . ?
C8 C7 C5 C4 1.02(15) . . . . ?
C8 C7 C5 C6 -176.02(16) . . . . ?
C23 O3 C22 O2 -4.53(19) . . . . ?
C23 O3 C22 N3 176.19(11) . . . . ?
C12 C11 C18 C17 -2.30(19) . . . . ?
C12 C13 C14 C9 -1.7(2) . . . . ?
C12 C15 C16 C17 -1.5(2) . . . . ?
C18 C11 C12 C13 -178.90(11) . . . . ?
C18 C11 C12 C15 1.15(17) . . . . ?
C4 N1 C19 O1 122.71(13) . . . . ?
C4 N1 C19 N2 -55.96(16) . . . . ?
C4 N1 C8 C9 178.80(10) . . . . ?
C4 N1 C8 C7 2.78(13) . . . . ?
C4 C5 C6 C1 -0.9(2) . . . . ?
C4 C3 C2 C1 0.5(3) . . . . ?
C7 C5 C6 C1 175.85(17) . . . . ?
C5 C4 C3 C2 -1.5(2) . . . . ?
C5 C6 C1 C2 0.0(3) . . . . ?
C13 C12 C15 C16 -179.21(14) . . . . ?
C14 C9 C8 N1 151.18(11) . . . . ?
C14 C9 C8 C7 -33.66(17) . . . . ?
C15 C12 C13 C14 163.83(13) . . . . ?
C15 C16 C17 C18 0.4(2) . . . . ?
C3 C4 C5 C7 -175.83(13) . . . . ?
C3 C4 C5 C6 1.7(2) . . . . ?
C3 C2 C1 C6 0.2(3) . . . . ?
C20 N2 C19 O1 157.22(14) . . . . ?
C20 N2 C19 N1 -24.18(18) . . . . ?
C21 N2 C19 O1 -10.8(2) . . . . ?
C21 N2 C19 N1 167.77(12) . . . . ?
