#------------------------------------------------------------------------------
#$Date: 2020-08-06 16:00:21 +0300 (Thu, 06 Aug 2020) $
#$Revision: 254896 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/67/7126724.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_7126724
loop_
_publ_author_name
'Wu, Lingang'
'Hao, Yanan'
'Liu, Yuxiu'
'Song, Haibin'
'Wang, Qingmin'
_publ_section_title
;
 Visible-light-induced dearomative oxamination of indole derivatives and
 dearomative amidation of phenol derivatives.
;
_journal_issue                   60
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8436
_journal_page_last               8439
_journal_paper_doi               10.1039/d0cc03506h
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C24 H26 N2 O4'
_chemical_formula_sum            'C24 H26 N2 O4'
_chemical_formula_weight         406.47
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-15 deposited with the CCDC.	2020-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                75.236(5)
_cell_angle_beta                 81.627(4)
_cell_angle_gamma                67.452(5)
_cell_formula_units_Z            2
_cell_length_a                   9.6454(4)
_cell_length_b                   10.4111(7)
_cell_length_c                   11.3573(5)
_cell_measurement_reflns_used    10214
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      32.9680
_cell_measurement_theta_min      1.8490
_cell_volume                     1017.07(10)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_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   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0281083000
_diffrn_orient_matrix_UB_12      -0.0300764000
_diffrn_orient_matrix_UB_13      0.0591178000
_diffrn_orient_matrix_UB_21      0.0076609000
_diffrn_orient_matrix_UB_22      0.0647949000
_diffrn_orient_matrix_UB_23      0.0010172000
_diffrn_orient_matrix_UB_31      -0.0742266000
_diffrn_orient_matrix_UB_32      0.0246940000
_diffrn_orient_matrix_UB_33      0.0262184000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10720
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.170
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0414
_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)+(0.0689P)²+0.2620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1135
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3684
_reflns_number_total             4138
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc03506h2.cif
_cod_data_source_block           r20191113b
_cod_depositor_comments          'Adding full bibliography for 7126724.cif.'
_cod_database_code               7126724
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_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   0.986
_shelx_estimated_absorpt_t_min   0.982
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,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:
 C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C20(H20), C21(H21), C22(H22), C23(H23),
 C24(H24)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.451
_oxdiff_exptl_absorpt_empirical_full_min 0.558
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
O1 O 0.56524(11) 0.20042(10) 0.01371(9) 0.0323(2) Uani 1 1 d . . . . .
O2 O 0.14640(11) 0.35906(10) 0.59058(8) 0.0260(2) Uani 1 1 d . . . . .
O3 O 0.21529(10) 0.10672(9) 0.20537(8) 0.0191(2) Uani 1 1 d . . . . .
O4 O 0.19433(11) -0.02872(10) 0.39201(9) 0.0303(2) Uani 1 1 d . . . . .
N1 N 0.37668(11) 0.23207(10) 0.15786(9) 0.0166(2) Uani 1 1 d . . . . .
N2 N 0.20511(11) 0.36030(11) 0.38702(9) 0.0173(2) Uani 1 1 d . . . . .
C1 C 0.15784(13) 0.42616(12) 0.16612(11) 0.0172(3) Uani 1 1 d . . . . .
C2 C 0.05253(15) 0.56100(13) 0.12688(11) 0.0225(3) Uani 1 1 d . . . . .
H2 H -0.037794 0.595764 0.174440 0.027 Uiso 1 1 calc R . . . .
C3 C 0.08163(16) 0.64442(14) 0.01654(12) 0.0262(3) Uani 1 1 d . . . . .
H3 H 0.010196 0.736542 -0.012736 0.031 Uiso 1 1 calc R . . . .
C4 C 0.21500(16) 0.59286(14) -0.05053(12) 0.0273(3) Uani 1 1 d . . . . .
H4 H 0.234815 0.652040 -0.124564 0.033 Uiso 1 1 calc R . . . .
C5 C 0.32121(15) 0.45676(14) -0.01284(11) 0.0238(3) Uani 1 1 d . . . . .
H5 H 0.412038 0.422410 -0.059956 0.029 Uiso 1 1 calc R . . . .
C6 C 0.28915(13) 0.37343(12) 0.09611(11) 0.0174(3) Uani 1 1 d . . . . .
C7 C 0.51707(14) 0.15149(13) 0.11294(11) 0.0192(3) Uani 1 1 d . . . . .
C8 C 0.61596(14) 0.00739(13) 0.18928(11) 0.0201(3) Uani 1 1 d . . . . .
C9 C 0.75903(15) -0.04971(15) 0.10956(13) 0.0295(3) Uani 1 1 d . . . . .
H9A H 0.732744 -0.069507 0.037625 0.044 Uiso 1 1 calc GR . . . .
H9B H 0.828924 -0.137664 0.156586 0.044 Uiso 1 1 calc GR . . . .
H9C H 0.806705 0.021600 0.083600 0.044 Uiso 1 1 calc GR . . . .
C10 C 0.66125(16) 0.03132(15) 0.30348(13) 0.0291(3) Uani 1 1 d . . . . .
H10A H 0.703272 0.106877 0.280018 0.044 Uiso 1 1 calc GR . . . .
H10B H 0.736853 -0.057042 0.344408 0.044 Uiso 1 1 calc GR . . . .
H10C H 0.572578 0.059418 0.359055 0.044 Uiso 1 1 calc GR . . . .
C11 C 0.54492(15) -0.10705(13) 0.22446(13) 0.0258(3) Uani 1 1 d . . . . .
H11A H 0.465510 -0.083879 0.288570 0.039 Uiso 1 1 calc GR . . . .
H11B H 0.622089 -0.200035 0.254466 0.039 Uiso 1 1 calc GR . . . .
H11C H 0.501765 -0.110373 0.152822 0.039 Uiso 1 1 calc GR . . . .
C12 C 0.28194(13) 0.18301(12) 0.25598(11) 0.0166(2) Uani 1 1 d . . . . .
H12 H 0.340374 0.121403 0.328732 0.020 Uiso 1 1 calc R . . . .
C13 C 0.17890(14) 0.00050(13) 0.28417(12) 0.0227(3) Uani 1 1 d . . . . .
C14 C 0.12042(18) -0.07219(16) 0.21629(14) 0.0324(3) Uani 1 1 d . . . . .
H14A H 0.037822 -0.001140 0.167162 0.049 Uiso 1 1 calc GR . . . .
H14B H 0.083775 -0.141033 0.274495 0.049 Uiso 1 1 calc GR . . . .
H14C H 0.201348 -0.122028 0.162740 0.049 Uiso 1 1 calc GR . . . .
C15 C 0.15856(13) 0.32174(12) 0.28579(10) 0.0165(2) Uani 1 1 d . . . . .
C16 C 0.12475(14) 0.33828(13) 0.49499(11) 0.0192(3) Uani 1 1 d . . . . .
C17 C 0.00858(15) 0.28341(14) 0.47441(12) 0.0234(3) Uani 1 1 d . . . . .
H17A H -0.090793 0.333861 0.511393 0.028 Uiso 1 1 calc R . . . .
H17B H 0.038215 0.179949 0.509794 0.028 Uiso 1 1 calc R . . . .
C18 C 0.00427(13) 0.31388(13) 0.33640(11) 0.0206(3) Uani 1 1 d . . . . .
H18A H -0.077522 0.405219 0.306490 0.025 Uiso 1 1 calc R . . . .
H18B H -0.012169 0.236773 0.311133 0.025 Uiso 1 1 calc R . . . .
C19 C 0.33283(13) 0.40195(13) 0.37646(10) 0.0174(3) Uani 1 1 d . . . . .
C20 C 0.32998(14) 0.53219(13) 0.30310(11) 0.0212(3) Uani 1 1 d . . . . .
H20 H 0.242657 0.595166 0.260935 0.025 Uiso 1 1 calc R . . . .
C21 C 0.45552(15) 0.56938(15) 0.29199(12) 0.0254(3) Uani 1 1 d . . . . .
H21 H 0.453847 0.658197 0.241846 0.030 Uiso 1 1 calc R . . . .
C22 C 0.58351(15) 0.47833(15) 0.35327(13) 0.0271(3) Uani 1 1 d . . . . .
H22 H 0.669334 0.504313 0.344601 0.033 Uiso 1 1 calc R . . . .
C23 C 0.58556(15) 0.34921(15) 0.42725(13) 0.0260(3) Uani 1 1 d . . . . .
H23 H 0.672912 0.286513 0.469493 0.031 Uiso 1 1 calc R . . . .
C24 C 0.45997(14) 0.31151(13) 0.43962(11) 0.0212(3) Uani 1 1 d . . . . .
H24 H 0.460956 0.223697 0.491370 0.025 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C13 O3 C12 116.99(9) . . ?
C6 N1 C12 108.05(9) . . ?
C7 N1 C6 123.36(10) . . ?
C7 N1 C12 127.52(10) . . ?
C16 N2 C15 113.77(10) . . ?
C16 N2 C19 122.74(10) . . ?
C19 N2 C15 123.16(9) . . ?
C2 C1 C6 121.04(11) . . ?
C2 C1 C15 128.60(11) . . ?
C6 C1 C15 110.22(10) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.71(12) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.81(12) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.0 . . ?
C3 C4 C5 122.08(12) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 H5 121.3 . . ?
C6 C5 C4 117.48(12) . . ?
C6 C5 H5 121.3 . . ?
C1 C6 N1 109.25(10) . . ?
C5 C6 N1 129.88(11) . . ?
C5 C6 C1 120.82(11) . . ?
O1 C7 N1 118.50(11) . . ?
O1 C7 C8 119.72(11) . . ?
N1 C7 C8 121.66(10) . . ?
C9 C8 C7 106.51(10) . . ?
C10 C8 C7 109.77(10) . . ?
C10 C8 C9 108.28(11) . . ?
C10 C8 C11 110.30(11) . . ?
C11 C8 C7 114.71(10) . . ?
C11 C8 C9 106.99(11) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 N1 105.92(9) . . ?
O3 C12 H12 111.8 . . ?
O3 C12 C15 110.23(9) . . ?
N1 C12 H12 111.8 . . ?
N1 C12 C15 104.90(9) . . ?
C15 C12 H12 111.8 . . ?
O3 C13 C14 110.03(11) . . ?
O4 C13 O3 123.45(12) . . ?
O4 C13 C14 126.52(12) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 C1 112.40(9) . . ?
N2 C15 C12 109.70(9) . . ?
N2 C15 C18 101.59(9) . . ?
C1 C15 C12 100.97(9) . . ?
C1 C15 C18 115.47(10) . . ?
C18 C15 C12 117.05(10) . . ?
O2 C16 N2 124.92(11) . . ?
O2 C16 C17 126.93(11) . . ?
N2 C16 C17 108.15(10) . . ?
C16 C17 H17A 110.9 . . ?
C16 C17 H17B 110.9 . . ?
C16 C17 C18 104.42(10) . . ?
H17A C17 H17B 108.9 . . ?
C18 C17 H17A 110.9 . . ?
C18 C17 H17B 110.9 . . ?
C15 C18 H18A 110.6 . . ?
C15 C18 H18B 110.6 . . ?
C17 C18 C15 105.58(10) . . ?
C17 C18 H18A 110.6 . . ?
C17 C18 H18B 110.6 . . ?
H18A C18 H18B 108.8 . . ?
C20 C19 N2 120.30(11) . . ?
C24 C19 N2 119.78(11) . . ?
C24 C19 C20 119.92(11) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.51(12) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 119.6 . . ?
C20 C21 C22 120.73(12) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.66(12) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.02(12) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 H24 119.9 . . ?
C23 C24 C19 120.15(12) . . ?
C23 C24 H24 119.9 . . ?
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
O1 C7 1.2174(15) . ?
O2 C16 1.2203(15) . ?
O3 C12 1.4514(14) . ?
O3 C13 1.3597(15) . ?
O4 C13 1.2013(16) . ?
N1 C6 1.4367(15) . ?
N1 C7 1.3940(16) . ?
N1 C12 1.4523(15) . ?
N2 C15 1.4861(14) . ?
N2 C16 1.3686(15) . ?
N2 C19 1.4354(15) . ?
C1 C2 1.3859(17) . ?
C1 C6 1.3906(17) . ?
C1 C15 1.5076(16) . ?
C2 H2 0.9500 . ?
C2 C3 1.3904(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3949(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3880(17) . ?
C7 C8 1.5468(17) . ?
C8 C9 1.5359(18) . ?
C8 C10 1.5324(18) . ?
C8 C11 1.5338(18) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12 1.0000 . ?
C12 C15 1.5590(17) . ?
C13 C14 1.4955(19) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C18 1.5402(16) . ?
C16 C17 1.5073(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5214(18) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.3913(17) . ?
C19 C24 1.3897(17) . ?
C20 H20 0.9500 . ?
C20 C21 1.3864(18) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.386(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.3886(19) . ?
C24 H24 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
O1 C7 C8 C9 -4.80(16) . . . . ?
O1 C7 C8 C10 112.22(13) . . . . ?
O1 C7 C8 C11 -122.95(13) . . . . ?
O2 C16 C17 C18 166.02(12) . . . . ?
O3 C12 C15 N2 152.45(9) . . . . ?
O3 C12 C15 C1 -88.75(10) . . . . ?
O3 C12 C15 C18 37.46(13) . . . . ?
N1 C7 C8 C9 179.20(11) . . . . ?
N1 C7 C8 C10 -63.79(14) . . . . ?
N1 C7 C8 C11 61.05(15) . . . . ?
N1 C12 C15 N2 -93.93(10) . . . . ?
N1 C12 C15 C1 24.86(11) . . . . ?
N1 C12 C15 C18 151.07(10) . . . . ?
N2 C15 C18 C17 -24.32(12) . . . . ?
N2 C16 C17 C18 -14.59(13) . . . . ?
N2 C19 C20 C21 -178.67(11) . . . . ?
N2 C19 C24 C23 178.21(11) . . . . ?
C1 C2 C3 C4 -1.07(19) . . . . ?
C1 C15 C18 C17 -146.22(10) . . . . ?
C2 C1 C6 N1 -179.67(10) . . . . ?
C2 C1 C6 C5 2.62(18) . . . . ?
C2 C1 C15 N2 -76.92(15) . . . . ?
C2 C1 C15 C12 166.25(12) . . . . ?
C2 C1 C15 C18 38.99(17) . . . . ?
C2 C3 C4 C5 1.9(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C4 C5 C6 N1 -179.00(12) . . . . ?
C4 C5 C6 C1 -1.82(18) . . . . ?
C6 N1 C7 O1 -3.50(18) . . . . ?
C6 N1 C7 C8 172.55(10) . . . . ?
C6 N1 C12 O3 92.67(10) . . . . ?
C6 N1 C12 C15 -23.94(11) . . . . ?
C6 C1 C2 C3 -1.13(18) . . . . ?
C6 C1 C15 N2 98.84(11) . . . . ?
C6 C1 C15 C12 -17.98(12) . . . . ?
C6 C1 C15 C18 -145.24(11) . . . . ?
C7 N1 C6 C1 -178.07(10) . . . . ?
C7 N1 C6 C5 -0.63(19) . . . . ?
C7 N1 C12 O3 -75.67(14) . . . . ?
C7 N1 C12 C15 167.72(11) . . . . ?
C12 O3 C13 O4 2.68(18) . . . . ?
C12 O3 C13 C14 -176.65(10) . . . . ?
C12 N1 C6 C1 13.00(12) . . . . ?
C12 N1 C6 C5 -169.57(12) . . . . ?
C12 N1 C7 O1 163.20(11) . . . . ?
C12 N1 C7 C8 -20.75(17) . . . . ?
C12 C15 C18 C17 95.10(12) . . . . ?
C13 O3 C12 N1 151.47(10) . . . . ?
C13 O3 C12 C15 -95.57(12) . . . . ?
C15 N2 C16 O2 178.02(11) . . . . ?
C15 N2 C16 C17 -1.38(13) . . . . ?
C15 N2 C19 C20 69.87(15) . . . . ?
C15 N2 C19 C24 -109.97(13) . . . . ?
C15 C1 C2 C3 174.23(12) . . . . ?
C15 C1 C6 N1 4.20(13) . . . . ?
C15 C1 C6 C5 -173.51(11) . . . . ?
C16 N2 C15 C1 140.37(10) . . . . ?
C16 N2 C15 C12 -108.15(11) . . . . ?
C16 N2 C15 C18 16.36(12) . . . . ?
C16 N2 C19 C20 -117.13(13) . . . . ?
C16 N2 C19 C24 63.02(16) . . . . ?
C16 C17 C18 C15 24.26(13) . . . . ?
C19 N2 C15 C1 -46.06(14) . . . . ?
C19 N2 C15 C12 65.42(13) . . . . ?
C19 N2 C15 C18 -170.07(10) . . . . ?
C19 N2 C16 O2 4.43(19) . . . . ?
C19 N2 C16 C17 -174.98(10) . . . . ?
C19 C20 C21 C22 -0.09(19) . . . . ?
C20 C19 C24 C23 -1.64(18) . . . . ?
C20 C21 C22 C23 -0.53(19) . . . . ?
C21 C22 C23 C24 0.1(2) . . . . ?
C22 C23 C24 C19 1.02(19) . . . . ?
C24 C19 C20 C21 1.17(18) . . . . ?
