#------------------------------------------------------------------------------
#$Date: 2024-07-05 20:56:51 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293253 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159961.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_7159961
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 H31 N3 O3'
_chemical_formula_sum            'C26 H31 N3 O3'
_chemical_formula_weight         433.54
_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
_audit_creation_date             2024-01-17
_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                101.248(3)
_cell_angle_beta                 90.923(3)
_cell_angle_gamma                107.566(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1717(2)
_cell_length_b                   10.4991(4)
_cell_length_c                   17.0401(6)
_cell_measurement_reflns_used    4531
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.8260
_cell_measurement_theta_min      4.7210
_cell_volume                     1195.87(8)
_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)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -17.00   1.00    2.00    --  -41.51 -38.00 120.00   91
  2  ω    -66.00  33.00   1.00    2.00    --  -41.51  38.00 -60.00   99
  3  ω    100.00 128.00   1.00    2.00    --   41.51 178.00 150.00   28
  4  ω    -26.00  70.00   1.00    2.00    --   41.51 -57.00   0.00   96
  5  ω    100.00 126.00   1.00    2.00    --   41.51 178.00   0.00   26
  6  ω     35.00 132.00   1.00    8.00    --  105.74 -45.00 -90.00   97
  7  ω     63.00  88.00   1.00    8.00    --  105.74 -61.00 -60.00   25
  8  ω     52.00  95.00   1.00    8.00    --  105.74 -94.00  90.00   43
  9  ω    105.00 132.00   1.00    8.00    --  105.74  77.00-150.00   27
 10  ω     30.00  93.00   1.00    8.00    --  105.74 -94.00 150.00   63
 11  ω     45.00 129.00   1.00    8.00    --  105.74 -45.00 120.00   84
 12  ω     49.00 105.00   1.00    8.00    --  105.74 -94.00  30.00   56
 13  ω     30.00 102.00   1.00    8.00    --  105.74 -30.00   0.00   72
 14  ω     75.00 113.00   1.00    8.00    --  105.74-125.00 -90.00   38
 15  ω    114.00 167.00   1.00    8.00    --  105.74  77.00  60.00   53
 16  ω     34.00 106.00   1.00    8.00    --  105.74-100.00 -66.00   72
 17  ω     67.00 177.00   1.00    8.00    --  105.74  15.00-180.00  110
;
_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      0.0649955000
_diffrn_orient_matrix_UB_12      -0.0088805000
_diffrn_orient_matrix_UB_13      0.0848453000
_diffrn_orient_matrix_UB_21      -0.0982925000
_diffrn_orient_matrix_UB_22      -0.1559899000
_diffrn_orient_matrix_UB_23      -0.0206688000
_diffrn_orient_matrix_UB_31      0.1929013000
_diffrn_orient_matrix_UB_32      -0.0191352000
_diffrn_orient_matrix_UB_33      -0.0304304000
_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  0.0194
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7935
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.806
_diffrn_reflns_theta_min         4.518
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87595
_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    1.204
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0039(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0399
_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)+(0.0610P)²+0.1406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1162
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3944
_reflns_number_total             4602
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00678j2.cif
_cod_data_source_block           cjz-24-1-3_auto
_cod_depositor_comments
'Adding full bibliography for 7159960--7159961.cif.'
_cod_original_cell_volume        1195.87(7)
_cod_database_code               7159961
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         c20h20o2n2
_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   0.911
_shelx_estimated_absorpt_t_min   0.873
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C10(H10), C1(H1A)
1.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B)
1.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C12(H12), C14(H14), C13(H13), C6(H6), C3(H3), C5(H5), C4(H4)
1.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C25(H25A,H25B,H25C), C22(H22A,H22B,H22C), C21(H21A,H21B,
 H21C), C23(H23A,H23B,H23C)
;
_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 1.472
_oxdiff_exptl_absorpt_empirical_full_min 0.669
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
O2 O 0.53779(17) 0.12977(9) 0.32904(6) 0.0531(3) Uani 1 1 d . . . . .
O3 O 0.57915(16) 0.61468(10) 0.12542(7) 0.0556(3) Uani 1 1 d . . . . .
O1 O 0.76029(16) 0.25176(11) 0.25609(8) 0.0610(3) Uani 1 1 d . . . . .
N2 N 0.65875(15) 0.41730(10) 0.11637(6) 0.0388(2) Uani 1 1 d . . . . .
N1 N 0.56797(18) 0.34628(11) 0.33660(7) 0.0433(3) Uani 1 1 d . . . . .
N3 N 0.89888(18) 0.62373(12) 0.11926(8) 0.0515(3) Uani 1 1 d . . . . .
C18 C 0.46695(18) 0.33466(12) 0.12709(7) 0.0366(3) Uani 1 1 d . . . . .
C10 C 0.42026(18) 0.47443(12) 0.26142(7) 0.0374(3) Uani 1 1 d . . . . .
H10 H 0.4564 0.5573 0.2393 0.045 Uiso 1 1 calc R U . . .
C24 C 0.70401(19) 0.55639(13) 0.12059(8) 0.0402(3) Uani 1 1 d . . . . .
C19 C 0.63398(19) 0.24298(13) 0.30232(8) 0.0403(3) Uani 1 1 d . . . . .
C1 C 0.60702(18) 0.47214(12) 0.30683(7) 0.0369(3) Uani 1 1 d . . . . .
H1A H 0.7107 0.4763 0.2698 0.044 Uiso 1 1 calc R U . . .
C2 C 0.6760(2) 0.59423(13) 0.37629(8) 0.0421(3) Uani 1 1 d . . . . .
C7 C 0.5333(2) 0.63351(14) 0.42166(8) 0.0442(3) Uani 1 1 d . . . . .
C15 C 0.4117(2) 0.21668(13) 0.06641(8) 0.0441(3) Uani 1 1 d . . . . .
C11 C 0.35141(18) 0.35383(12) 0.19079(8) 0.0382(3) Uani 1 1 d . . . . .
C8 C 0.3271(2) 0.56291(15) 0.39531(9) 0.0493(3) Uani 1 1 d . . . . .
H8 H 0.2325 0.5698 0.4312 0.059 Uiso 1 1 calc R U . . .
C9 C 0.2708(2) 0.48889(14) 0.32134(9) 0.0458(3) Uani 1 1 d . . . . .
H9 H 0.1380 0.4455 0.3063 0.055 Uiso 1 1 calc R U . . .
C12 C 0.1734(2) 0.25006(14) 0.18791(10) 0.0494(3) Uani 1 1 d . . . . .
H12 H 0.0909 0.2586 0.2288 0.059 Uiso 1 1 calc R U . . .
C20 C 0.5661(2) -0.00238(14) 0.29686(9) 0.0508(3) Uani 1 1 d . . . . .
C14 C 0.2350(2) 0.11680(14) 0.06553(10) 0.0532(4) Uani 1 1 d . . . . .
H14 H 0.1974 0.0388 0.0248 0.064 Uiso 1 1 calc R U . . .
C16 C 0.5703(2) 0.22215(15) 0.00938(9) 0.0535(4) Uani 1 1 d . . . . .
H16A H 0.5370 0.2486 -0.0391 0.064 Uiso 1 1 calc R U . . .
H16B H 0.5946 0.1348 -0.0049 0.064 Uiso 1 1 calc R U . . .
C17 C 0.7469(2) 0.33147(15) 0.05837(9) 0.0505(3) Uani 1 1 d . . . . .
H17A H 0.8252 0.2905 0.0861 0.061 Uiso 1 1 calc R U . . .
H17B H 0.8290 0.3851 0.0242 0.061 Uiso 1 1 calc R U . . .
C13 C 0.1151(2) 0.13504(15) 0.12641(11) 0.0569(4) Uani 1 1 d . . . . .
H13 H -0.0059 0.0695 0.1262 0.068 Uiso 1 1 calc R U . . .
C6 C 0.5944(3) 0.74178(16) 0.48820(9) 0.0567(4) Uani 1 1 d . . . . .
H6 H 0.5012 0.7685 0.5188 0.068 Uiso 1 1 calc R U . . .
C3 C 0.8722(2) 0.66408(17) 0.39727(10) 0.0587(4) Uani 1 1 d . . . . .
H3 H 0.9665 0.6390 0.3667 0.070 Uiso 1 1 calc R U . . .
C26 C 1.0527(2) 0.58307(19) 0.15385(11) 0.0628(4) Uani 1 1 d . . . . .
H26A H 1.1147 0.6494 0.2014 0.094 Uiso 1 1 calc R U . . .
H26B H 1.1484 0.5774 0.1157 0.094 Uiso 1 1 calc R U . . .
H26C H 0.9968 0.4955 0.1673 0.094 Uiso 1 1 calc R U . . .
C5 C 0.7903(3) 0.80937(19) 0.50912(11) 0.0701(5) Uani 1 1 d . . . . .
H5 H 0.8288 0.8807 0.5539 0.084 Uiso 1 1 calc R U . . .
C25 C 0.9515(3) 0.76746(16) 0.11533(13) 0.0689(5) Uani 1 1 d . . . . .
H25A H 0.8547 0.7808 0.0810 0.103 Uiso 1 1 calc R U . . .
H25B H 1.0774 0.7947 0.0942 0.103 Uiso 1 1 calc R U . . .
H25C H 0.9570 0.8216 0.1682 0.103 Uiso 1 1 calc R U . . .
C4 C 0.9301(3) 0.7716(2) 0.46373(12) 0.0756(5) Uani 1 1 d . . . . .
H4 H 1.0627 0.8180 0.4776 0.091 Uiso 1 1 calc R U . . .
C22 C 0.5259(3) -0.03983(19) 0.20651(11) 0.0729(5) Uani 1 1 d . . . . .
H22A H 0.4024 -0.0290 0.1922 0.109 Uiso 1 1 calc R U . . .
H22B H 0.5212 -0.1331 0.1875 0.109 Uiso 1 1 calc R U . . .
H22C H 0.6285 0.0189 0.1826 0.109 Uiso 1 1 calc R U . . .
C21 C 0.4100(4) -0.09792(18) 0.33556(14) 0.0803(6) Uani 1 1 d . . . . .
H21A H 0.4348 -0.0714 0.3929 0.120 Uiso 1 1 calc R U . . .
H21B H 0.4131 -0.1898 0.3179 0.120 Uiso 1 1 calc R U . . .
H21C H 0.2833 -0.0930 0.3204 0.120 Uiso 1 1 calc R U . . .
C23 C 0.7698(3) -0.0002(2) 0.32249(14) 0.0810(6) Uani 1 1 d . . . . .
H23A H 0.8650 0.0639 0.2987 0.122 Uiso 1 1 calc R U . . .
H23B H 0.7825 -0.0897 0.3052 0.122 Uiso 1 1 calc R U . . .
H23C H 0.7915 0.0266 0.3799 0.122 Uiso 1 1 calc R U . . .
H1 H 0.472(3) 0.3273(18) 0.3654(11) 0.058(5) 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'
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
C19 O2 C20 121.48(11) . . ?
C18 N2 C17 107.50(10) . . ?
C24 N2 C18 122.14(10) . . ?
C24 N2 C17 121.50(11) . . ?
C19 N1 C1 122.40(11) . . ?
C19 N1 H1 117.2(12) . . ?
C1 N1 H1 117.2(12) . . ?
C24 N3 C26 122.84(12) . . ?
C24 N3 C25 116.79(12) . . ?
C26 N3 C25 115.28(14) . . ?
C15 C18 N2 109.38(11) . . ?
C11 C18 N2 128.33(11) . . ?
C11 C18 C15 121.99(12) . . ?
C1 C10 H10 107.0 . . ?
C11 C10 H10 107.0 . . ?
C11 C10 C1 110.89(9) . . ?
C9 C10 H10 107.0 . . ?
C9 C10 C1 108.60(10) . . ?
C9 C10 C11 115.92(11) . . ?
O3 C24 N2 122.60(12) . . ?
O3 C24 N3 122.54(12) . . ?
N3 C24 N2 114.86(11) . . ?
O1 C19 O2 125.98(11) . . ?
O1 C19 N1 125.02(12) . . ?
N1 C19 O2 108.99(11) . . ?
N1 C1 C10 110.15(10) . . ?
N1 C1 H1A 108.9 . . ?
N1 C1 C2 109.77(10) . . ?
C10 C1 H1A 108.9 . . ?
C2 C1 C10 110.33(9) . . ?
C2 C1 H1A 108.9 . . ?
C7 C2 C1 117.95(12) . . ?
C3 C2 C1 122.30(12) . . ?
C3 C2 C7 119.73(13) . . ?
C2 C7 C8 118.43(12) . . ?
C6 C7 C2 118.78(14) . . ?
C6 C7 C8 122.74(13) . . ?
C18 C15 C16 109.62(12) . . ?
C14 C15 C18 120.65(13) . . ?
C14 C15 C16 129.73(13) . . ?
C18 C11 C10 122.24(11) . . ?
C18 C11 C12 115.62(12) . . ?
C12 C11 C10 122.01(12) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 C7 121.71(12) . . ?
C9 C8 H8 119.1 . . ?
C10 C9 H9 119.6 . . ?
C8 C9 C10 120.74(13) . . ?
C8 C9 H9 119.6 . . ?
C11 C12 H12 118.7 . . ?
C13 C12 C11 122.51(13) . . ?
C13 C12 H12 118.7 . . ?
O2 C20 C22 110.58(12) . . ?
O2 C20 C21 101.84(12) . . ?
O2 C20 C23 110.31(14) . . ?
C22 C20 C21 110.24(16) . . ?
C23 C20 C22 111.80(15) . . ?
C23 C20 C21 111.66(16) . . ?
C15 C14 H14 120.7 . . ?
C15 C14 C13 118.55(13) . . ?
C13 C14 H14 120.7 . . ?
C15 C16 H16A 111.3 . . ?
C15 C16 H16B 111.3 . . ?
C15 C16 C17 102.38(11) . . ?
H16A C16 H16B 109.2 . . ?
C17 C16 H16A 111.3 . . ?
C17 C16 H16B 111.3 . . ?
N2 C17 C16 104.11(11) . . ?
N2 C17 H17A 110.9 . . ?
N2 C17 H17B 110.9 . . ?
C16 C17 H17A 110.9 . . ?
C16 C17 H17B 110.9 . . ?
H17A C17 H17B 109.0 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.60(13) . . ?
C14 C13 H13 119.7 . . ?
C7 C6 H6 119.5 . . ?
C5 C6 C7 120.94(14) . . ?
C5 C6 H6 119.5 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.64(15) . . ?
C4 C3 H3 119.7 . . ?
N3 C26 H26A 109.5 . . ?
N3 C26 H26B 109.5 . . ?
N3 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 120.10(15) . . ?
C4 C5 H5 120.0 . . ?
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 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.81(18) . . ?
C5 C4 H4 120.1 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
O2 C19 1.3499(16) . ?
O2 C20 1.4640(15) . ?
O3 C24 1.2233(16) . ?
O1 C19 1.2043(17) . ?
N2 C18 1.4241(16) . ?
N2 C24 1.3839(16) . ?
N2 C17 1.4851(16) . ?
N1 C19 1.3466(16) . ?
N1 C1 1.4576(15) . ?
N1 H1 0.851(19) . ?
N3 C24 1.3655(18) . ?
N3 C26 1.452(2) . ?
N3 C25 1.4562(19) . ?
C18 C15 1.3970(18) . ?
C18 C11 1.3963(18) . ?
C10 H10 0.9800 . ?
C10 C1 1.5449(17) . ?
C10 C11 1.5180(17) . ?
C10 C9 1.5125(17) . ?
C1 H1A 0.9800 . ?
C1 C2 1.5149(17) . ?
C2 C7 1.4039(18) . ?
C2 C3 1.380(2) . ?
C7 C8 1.458(2) . ?
C7 C6 1.397(2) . ?
C15 C14 1.377(2) . ?
C15 C16 1.503(2) . ?
C11 C12 1.3991(19) . ?
C8 H8 0.9300 . ?
C8 C9 1.330(2) . ?
C9 H9 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.385(2) . ?
C20 C22 1.513(2) . ?
C20 C21 1.516(2) . ?
C20 C23 1.511(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.379(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.528(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C13 H13 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.374(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(2) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C4 1.380(3) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C4 H4 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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 C18 C15 C14 177.04(12) . . . . ?
N2 C18 C15 C16 -2.61(14) . . . . ?
N2 C18 C11 C10 0.45(19) . . . . ?
N2 C18 C11 C12 -175.57(12) . . . . ?
N1 C1 C2 C7 -81.37(14) . . . . ?
N1 C1 C2 C3 96.65(15) . . . . ?
C18 N2 C24 O3 -7.78(19) . . . . ?
C18 N2 C24 N3 171.99(11) . . . . ?
C18 N2 C17 C16 25.11(14) . . . . ?
C18 C15 C14 C13 -0.8(2) . . . . ?
C18 C15 C16 C17 17.76(15) . . . . ?
C18 C11 C12 C13 0.5(2) . . . . ?
C10 C1 C2 C7 40.21(15) . . . . ?
C10 C1 C2 C3 -141.77(14) . . . . ?
C10 C11 C12 C13 -175.57(13) . . . . ?
C24 N2 C18 C15 133.19(12) . . . . ?
C24 N2 C18 C11 -53.17(18) . . . . ?
C24 N2 C17 C16 -122.82(13) . . . . ?
C19 O2 C20 C22 -55.16(19) . . . . ?
C19 O2 C20 C21 -172.30(15) . . . . ?
C19 O2 C20 C23 69.03(19) . . . . ?
C19 N1 C1 C10 105.25(14) . . . . ?
C19 N1 C1 C2 -133.07(13) . . . . ?
C1 N1 C19 O2 -165.19(12) . . . . ?
C1 N1 C19 O1 15.6(2) . . . . ?
C1 C10 C11 C18 -61.60(14) . . . . ?
C1 C10 C11 C12 114.17(13) . . . . ?
C1 C10 C9 C8 34.58(16) . . . . ?
C1 C2 C7 C8 -5.40(17) . . . . ?
C1 C2 C7 C6 177.03(11) . . . . ?
C1 C2 C3 C4 -176.92(15) . . . . ?
C2 C7 C8 C9 -16.9(2) . . . . ?
C2 C7 C6 C5 0.2(2) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C7 C2 C3 C4 1.1(2) . . . . ?
C7 C8 C9 C10 0.4(2) . . . . ?
C7 C6 C5 C4 0.7(3) . . . . ?
C15 C18 C11 C10 173.37(11) . . . . ?
C15 C18 C11 C12 -2.65(18) . . . . ?
C15 C14 C13 C12 -1.3(2) . . . . ?
C15 C16 C17 N2 -25.33(14) . . . . ?
C11 C18 C15 C14 2.92(19) . . . . ?
C11 C18 C15 C16 -176.72(12) . . . . ?
C11 C10 C1 N1 -59.58(13) . . . . ?
C11 C10 C1 C2 179.07(10) . . . . ?
C11 C10 C9 C8 160.16(12) . . . . ?
C11 C12 C13 C14 1.5(2) . . . . ?
C8 C7 C6 C5 -177.28(15) . . . . ?
C9 C10 C1 N1 68.89(12) . . . . ?
C9 C10 C1 C2 -52.46(13) . . . . ?
C9 C10 C11 C18 174.00(11) . . . . ?
C9 C10 C11 C12 -10.23(17) . . . . ?
C20 O2 C19 O1 -6.3(2) . . . . ?
C20 O2 C19 N1 174.57(12) . . . . ?
C14 C15 C16 C17 -161.85(14) . . . . ?
C16 C15 C14 C13 178.73(15) . . . . ?
C17 N2 C18 C15 -14.49(14) . . . . ?
C17 N2 C18 C11 159.14(13) . . . . ?
C17 N2 C24 O3 135.50(14) . . . . ?
C17 N2 C24 N3 -44.74(17) . . . . ?
C6 C7 C8 C9 160.54(14) . . . . ?
C6 C5 C4 C3 -0.7(3) . . . . ?
C3 C2 C7 C8 176.53(13) . . . . ?
C3 C2 C7 C6 -1.0(2) . . . . ?
C26 N3 C24 O3 147.24(15) . . . . ?
C26 N3 C24 N2 -32.5(2) . . . . ?
C25 N3 C24 O3 -6.3(2) . . . . ?
C25 N3 C24 N2 173.94(14) . . . . ?
