#------------------------------------------------------------------------------
#$Date: 2022-03-05 00:24:00 +0200 (Sat, 05 Mar 2022) $
#$Revision: 273419 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/84/7158492.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_7158492
loop_
_publ_author_name
'Liyu, Jessica'
'Kim, Shi-Wei'
'Söhnel, Tilo'
'Sperry, Jonathan'
_publ_section_title
;
 Progress toward a biomimetic synthesis of pegaharmaline A.
;
_journal_issue                   6
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1275
_journal_page_last               1283
_journal_paper_doi               10.1039/d1ob02372a
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C23 H22 N4 O2'
_chemical_formula_sum            'C23 H22 N4 O2'
_chemical_formula_weight         386.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-12-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-12-02 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.333(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0831(2)
_cell_length_b                   9.0813(2)
_cell_length_c                   18.4230(3)
_cell_measurement_reflns_used    9085
_cell_measurement_temperature    109(2)
_cell_measurement_theta_max      74.3610
_cell_measurement_theta_min      4.0420
_cell_volume                     1974.91(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      109(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_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    104.00 132.00   0.50    0.49    --  102.39 111.00-150.00   56
  2  ω    141.00 166.00   0.50    0.49    --  102.39 111.00-150.00   50
  3  ω    100.00 164.00   0.50    0.49    --  102.39 111.00 -90.00  128
  4  ω    102.00 143.00   0.50    0.49    --  102.39 111.00 -60.00   82
  5  ω     79.00 115.00   0.50    0.49    --  102.39-111.00  60.00   72
  6  ω     63.00 109.00   0.50    0.49    --  102.39 -95.00 120.00   92
  7  ω     27.00  53.00   0.50    0.49    --  102.39-111.00  60.00   52
  8  ω      1.00  84.00   0.50    0.12    --   47.48 -99.00 150.00  166
  9  ω   -123.00 -74.00   0.50    0.12    --  -47.48-125.00 150.00   98
 10  ω   -124.00 -73.00   0.50    0.12    --  -47.48-125.00 120.00  102
 11  ω   -123.00 -70.00   0.50    0.12    --  -47.48-125.00 -60.00  106
 12  ω   -115.00 -72.00   0.50    0.12    --  -47.48-125.00-180.00   86
 13  ω   -136.00 -90.00   0.50    0.49    --  -90.25 -95.00-180.00   92
 14  ω   -141.00-116.00   0.50    0.49    --  -90.25 -59.00-141.00   50
 15  ω    -19.00  28.00   0.50    0.12    --   47.48 -59.00-141.00   94
 16  ω     55.00  99.00   0.50    0.49    --  102.39 -59.00-141.00   88
 17  ω     29.00 122.00   0.50    0.49    --  102.39 -45.00-150.00  186
 18  ω    -98.00 -73.00   0.50    0.12    --  -47.48 -59.00-141.00   50
 19  ω   -105.00 -53.00   0.50    0.49    --  -90.25  59.00  -1.00  104
 20  ω    -92.00 -66.00   0.50    0.49    --  -90.25  45.00 120.00   52
 21  ω     55.00  80.00   0.50    0.12    --   47.48  59.00  -1.00   50
 22  ω     83.00 163.00   0.50    0.49    --  102.39  30.00  90.00  160
 23  ω     81.00 173.00   0.50    0.49    --  102.39  59.00  -1.00  184
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1073698000
_diffrn_orient_matrix_UB_12      0.0366225000
_diffrn_orient_matrix_UB_13      0.0590166000
_diffrn_orient_matrix_UB_21      -0.0354700000
_diffrn_orient_matrix_UB_22      -0.1124738000
_diffrn_orient_matrix_UB_23      0.0533842000
_diffrn_orient_matrix_UB_31      0.0650729000
_diffrn_orient_matrix_UB_32      -0.1216776000
_diffrn_orient_matrix_UB_33      -0.0315517000
_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  0.0341
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13539
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.737
_diffrn_reflns_theta_min         6.149
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67396
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3567
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0366
_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)+(0.0499P)²+0.5149P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0974
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3170
_reflns_number_total             3567
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob02372a2.cif
_cod_data_source_block           jl3_8
_cod_depositor_comments
'Adding full bibliography for 7158492--7158494.cif.'
_cod_database_code               7158492
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C23H22N4O2
_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   0.935
_shelx_estimated_absorpt_t_min   0.811
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C17(H17), C20(H20), C21(H21), C22(H22),
 C23(H23), N3(H3A)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
;
_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 1.294
_oxdiff_exptl_absorpt_empirical_full_min 0.632
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
C1 C 0.57341(10) 0.84462(14) 0.34365(7) 0.0239(3) Uani 1 1 d . . . . .
H1 H 0.504940 0.875862 0.353720 0.029 Uiso 1 1 calc R U . . .
C2 C 0.62011(11) 0.92051(15) 0.29282(7) 0.0269(3) Uani 1 1 d . . . . .
H2 H 0.582734 1.001370 0.267942 0.032 Uiso 1 1 calc R U . . .
C3 C 0.72411(11) 0.87507(14) 0.27893(7) 0.0261(3) Uani 1 1 d . . . . .
H3 H 0.756622 0.927744 0.245539 0.031 Uiso 1 1 calc R U . . .
C4 C 0.77916(10) 0.75344(14) 0.31396(7) 0.0231(3) Uani 1 1 d . . . . .
H4 H 0.848093 0.723952 0.303973 0.028 Uiso 1 1 calc R U . . .
C5 C 0.73087(10) 0.67408(13) 0.36482(6) 0.0198(3) Uani 1 1 d . . . . .
C6 C 0.62788(10) 0.72078(13) 0.38039(6) 0.0204(3) Uani 1 1 d . . . . .
C7 C 0.57787(10) 0.63255(13) 0.43204(7) 0.0203(3) Uani 1 1 d . . . . .
C8 C 0.75750(10) 0.48870(13) 0.46449(6) 0.0192(3) Uani 1 1 d . . . . .
C9 C 0.78840(10) 0.32533(13) 0.47051(7) 0.0212(3) Uani 1 1 d . . . . .
C10 C 0.72412(12) 0.21829(15) 0.41616(8) 0.0300(3) Uani 1 1 d . . . . .
H10A H 0.753357 0.120945 0.428114 0.045 Uiso 1 1 calc R U . . .
H10B H 0.732077 0.243900 0.366982 0.045 Uiso 1 1 calc R U . . .
H10C H 0.645479 0.221037 0.418373 0.045 Uiso 1 1 calc R U . . .
C11 C 0.87831(10) 0.30421(14) 0.52566(7) 0.0211(3) Uani 1 1 d . . . . .
C12 C 0.94468(11) 0.16761(15) 0.54943(7) 0.0272(3) Uani 1 1 d . . . . .
H12A H 0.901238 0.083252 0.528807 0.041 Uiso 1 1 calc R U . . .
H12B H 0.961359 0.161144 0.602673 0.041 Uiso 1 1 calc R U . . .
H12C H 1.014159 0.170504 0.532127 0.041 Uiso 1 1 calc R U . . .
C13 C 0.90894(10) 0.44720(14) 0.56469(6) 0.0199(3) Uani 1 1 d . . . . .
C14 C 0.83433(10) 0.70262(13) 0.55387(7) 0.0211(3) Uani 1 1 d . . . . .
H14A H 0.808096 0.763501 0.510335 0.025 Uiso 1 1 calc R U . . .
H14B H 0.911559 0.731371 0.575760 0.025 Uiso 1 1 calc R U . . .
C15 C 0.75977(11) 0.73124(14) 0.60999(7) 0.0245(3) Uani 1 1 d . . . . .
H15A H 0.685340 0.689026 0.591518 0.029 Uiso 1 1 calc R U . . .
H15B H 0.792833 0.683214 0.656612 0.029 Uiso 1 1 calc R U . . .
C16 C 0.74807(10) 0.89248(14) 0.62323(7) 0.0226(3) Uani 1 1 d . . . . .
C17 C 0.66759(11) 0.98351(16) 0.58378(7) 0.0280(3) Uani 1 1 d . . . . .
H17 H 0.609378 0.953546 0.544989 0.034 Uiso 1 1 calc R U . . .
C18 C 0.77681(11) 1.12902(14) 0.66710(7) 0.0253(3) Uani 1 1 d . . . . .
C19 C 0.82067(10) 0.98409(14) 0.67662(7) 0.0222(3) Uani 1 1 d . . . . .
C20 C 0.91998(11) 0.95872(15) 0.73041(7) 0.0277(3) Uani 1 1 d . . . . .
H20 H 0.951303 0.864904 0.737388 0.033 Uiso 1 1 calc R U . . .
C21 C 0.97030(13) 1.07565(17) 0.77276(8) 0.0349(3) Uani 1 1 d . . . . .
H21 H 1.036599 1.059928 0.808197 0.042 Uiso 1 1 calc R U . . .
C22 C 0.92393(13) 1.21730(17) 0.76364(8) 0.0359(3) Uani 1 1 d . . . . .
H22 H 0.959252 1.293302 0.793746 0.043 Uiso 1 1 calc R U . . .
C23 C 0.82687(13) 1.24655(15) 0.71091(8) 0.0332(3) Uani 1 1 d . . . . .
H23 H 0.796060 1.340736 0.704797 0.040 Uiso 1 1 calc R U . . .
N1 N 0.78149(9) 0.54682(11) 0.39659(6) 0.0207(2) Uani 1 1 d . . . . .
N2 N 0.83329(8) 0.54906(11) 0.53105(5) 0.0197(2) Uani 1 1 d . . . . .
N3 N 0.68430(9) 1.12574(13) 0.60923(7) 0.0307(3) Uani 1 1 d . . . . .
H3A H 0.643420 1.200395 0.591726 0.037 Uiso 1 1 calc R U . . .
N4 N 0.63904(8) 0.51633(12) 0.46449(6) 0.0198(2) Uani 1 1 d . . . . .
O1 O 0.48275(7) 0.65810(10) 0.44532(5) 0.0256(2) Uani 1 1 d . . . . .
O2 O 0.98828(7) 0.47137(10) 0.61752(5) 0.0247(2) Uani 1 1 d . . . . .
H4A H 0.6078(13) 0.4639(17) 0.4953(9) 0.026(4) Uiso 1 1 d . . . . .
H1A H 0.8505(15) 0.5348(18) 0.3934(9) 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'
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
C2 C1 H1 119.6 . . ?
C2 C1 C6 120.76(12) . . ?
C6 C1 H1 119.6 . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.47(12) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.96(12) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.78(11) . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.68(11) . . ?
N1 C5 C4 120.26(11) . . ?
N1 C5 C6 119.99(11) . . ?
C1 C6 C7 122.31(11) . . ?
C5 C6 C1 119.32(11) . . ?
C5 C6 C7 118.28(11) . . ?
N4 C7 C6 116.77(10) . . ?
O1 C7 C6 123.33(11) . . ?
O1 C7 N4 119.88(11) . . ?
N1 C8 C9 109.07(9) . . ?
N1 C8 N2 112.45(10) . . ?
N1 C8 N4 108.48(9) . . ?
N2 C8 C9 101.68(9) . . ?
N4 C8 C9 113.14(10) . . ?
N4 C8 N2 111.94(9) . . ?
C10 C9 C8 120.04(10) . . ?
C11 C9 C8 109.97(11) . . ?
C11 C9 C10 129.89(12) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 C12 130.02(12) . . ?
C9 C11 C13 108.66(11) . . ?
C12 C11 C13 121.33(11) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C11 107.47(10) . . ?
O2 C13 C11 127.39(11) . . ?
O2 C13 N2 125.14(12) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
N2 C14 H14A 109.0 . . ?
N2 C14 H14B 109.0 . . ?
N2 C14 C15 112.79(10) . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 C14 111.46(10) . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C17 C16 C15 126.06(12) . . ?
C17 C16 C19 106.02(11) . . ?
C19 C16 C15 127.86(11) . . ?
C16 C17 H17 124.7 . . ?
C16 C17 N3 110.63(12) . . ?
N3 C17 H17 124.7 . . ?
C23 C18 C19 122.33(13) . . ?
N3 C18 C19 107.32(11) . . ?
N3 C18 C23 130.34(12) . . ?
C18 C19 C16 107.23(11) . . ?
C20 C19 C16 133.98(12) . . ?
C20 C19 C18 118.78(12) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 C19 118.71(13) . . ?
C21 C20 H20 120.6 . . ?
C20 C21 H21 119.2 . . ?
C20 C21 C22 121.54(13) . . ?
C22 C21 H21 119.2 . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.34(13) . . ?
C23 C22 H22 119.3 . . ?
C18 C23 H23 121.4 . . ?
C22 C23 C18 117.27(13) . . ?
C22 C23 H23 121.4 . . ?
C5 N1 C8 121.45(10) . . ?
C5 N1 H1A 115.4(11) . . ?
C8 N1 H1A 113.1(11) . . ?
C13 N2 C8 111.49(10) . . ?
C13 N2 C14 123.98(10) . . ?
C14 N2 C8 124.28(10) . . ?
C17 N3 H3A 125.6 . . ?
C18 N3 C17 108.78(11) . . ?
C18 N3 H3A 125.6 . . ?
C7 N4 C8 125.46(10) . . ?
C7 N4 H4A 115.8(10) . . ?
C8 N4 H4A 117.5(10) . . ?
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
C1 H1 0.9300 . ?
C1 C2 1.3769(18) . ?
C1 C6 1.4022(17) . ?
C2 H2 0.9300 . ?
C2 C3 1.3973(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.3768(18) . ?
C4 H4 0.9300 . ?
C4 C5 1.4040(18) . ?
C5 C6 1.4012(17) . ?
C5 N1 1.3781(16) . ?
C6 C7 1.4690(17) . ?
C7 N4 1.3524(16) . ?
C7 O1 1.2469(15) . ?
C8 C9 1.5281(17) . ?
C8 N1 1.4432(15) . ?
C8 N2 1.4707(15) . ?
C8 N4 1.4531(15) . ?
C9 C10 1.4894(18) . ?
C9 C11 1.3334(17) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.4912(17) . ?
C11 C13 1.4922(18) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N2 1.3540(15) . ?
C13 O2 1.2311(15) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.5316(17) . ?
C14 N2 1.4558(16) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.4961(18) . ?
C16 C17 1.3620(18) . ?
C16 C19 1.4356(18) . ?
C17 H17 0.9300 . ?
C17 N3 1.3742(19) . ?
C18 C19 1.4157(18) . ?
C18 C23 1.396(2) . ?
C18 N3 1.3704(18) . ?
C19 C20 1.4025(19) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.399(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.380(2) . ?
C23 H23 0.9300 . ?
N1 H1A 0.856(18) . ?
N3 H3A 0.8600 . ?
N4 H4A 0.885(17) . ?
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
C1 C2 C3 C4 1.6(2) . . . . ?
C1 C6 C7 N4 -179.50(11) . . . . ?
C1 C6 C7 O1 2.19(19) . . . . ?
C2 C1 C6 C5 -0.16(19) . . . . ?
C2 C1 C6 C7 -176.77(12) . . . . ?
C2 C3 C4 C5 -0.44(19) . . . . ?
C3 C4 C5 C6 -1.03(18) . . . . ?
C3 C4 C5 N1 175.82(11) . . . . ?
C4 C5 C6 C1 1.32(18) . . . . ?
C4 C5 C6 C7 178.07(11) . . . . ?
C4 C5 N1 C8 159.99(11) . . . . ?
C5 C6 C7 N4 3.86(16) . . . . ?
C5 C6 C7 O1 -174.45(11) . . . . ?
C6 C1 C2 C3 -1.3(2) . . . . ?
C6 C5 N1 C8 -23.18(17) . . . . ?
C6 C7 N4 C8 13.04(17) . . . . ?
C8 C9 C11 C12 -174.97(11) . . . . ?
C8 C9 C11 C13 4.57(13) . . . . ?
C9 C8 N1 C5 159.23(10) . . . . ?
C9 C8 N2 C13 8.51(12) . . . . ?
C9 C8 N2 C14 -177.11(10) . . . . ?
C9 C8 N4 C7 -152.40(11) . . . . ?
C9 C11 C13 N2 0.91(13) . . . . ?
C9 C11 C13 O2 -178.67(12) . . . . ?
C10 C9 C11 C12 1.6(2) . . . . ?
C10 C9 C11 C13 -178.90(12) . . . . ?
C11 C13 N2 C8 -6.27(12) . . . . ?
C11 C13 N2 C14 179.33(10) . . . . ?
C12 C11 C13 N2 -179.50(10) . . . . ?
C12 C11 C13 O2 0.92(18) . . . . ?
C14 C15 C16 C17 88.73(15) . . . . ?
C14 C15 C16 C19 -88.05(15) . . . . ?
C15 C14 N2 C8 94.26(13) . . . . ?
C15 C14 N2 C13 -92.05(13) . . . . ?
C15 C16 C17 N3 -177.84(11) . . . . ?
C15 C16 C19 C18 178.66(11) . . . . ?
C15 C16 C19 C20 0.5(2) . . . . ?
C16 C17 N3 C18 -0.62(15) . . . . ?
C16 C19 C20 C21 178.95(13) . . . . ?
C17 C16 C19 C18 1.37(13) . . . . ?
C17 C16 C19 C20 -176.82(13) . . . . ?
C18 C19 C20 C21 0.92(18) . . . . ?
C19 C16 C17 N3 -0.49(14) . . . . ?
C19 C18 C23 C22 1.55(19) . . . . ?
C19 C18 N3 C17 1.48(14) . . . . ?
C19 C20 C21 C22 0.6(2) . . . . ?
C20 C21 C22 C23 -1.2(2) . . . . ?
C21 C22 C23 C18 0.1(2) . . . . ?
C23 C18 C19 C16 179.41(11) . . . . ?
C23 C18 C19 C20 -2.07(18) . . . . ?
C23 C18 N3 C17 -179.82(13) . . . . ?
N1 C5 C6 C1 -175.53(11) . . . . ?
N1 C5 C6 C7 1.22(17) . . . . ?
N1 C8 C9 C10 -65.82(14) . . . . ?
N1 C8 C9 C11 111.10(11) . . . . ?
N1 C8 N2 C13 -108.00(11) . . . . ?
N1 C8 N2 C14 66.38(14) . . . . ?
N1 C8 N4 C7 -31.23(16) . . . . ?
N2 C8 C9 C10 175.23(11) . . . . ?
N2 C8 C9 C11 -7.85(12) . . . . ?
N2 C8 N1 C5 -88.78(13) . . . . ?
N2 C8 N4 C7 93.43(13) . . . . ?
N2 C14 C15 C16 -171.07(10) . . . . ?
N3 C18 C19 C16 -1.75(13) . . . . ?
N3 C18 C19 C20 176.76(11) . . . . ?
N3 C18 C23 C22 -176.98(13) . . . . ?
N4 C8 C9 C10 55.02(15) . . . . ?
N4 C8 C9 C11 -128.06(11) . . . . ?
N4 C8 N1 C5 35.58(15) . . . . ?
N4 C8 N2 C13 129.57(10) . . . . ?
N4 C8 N2 C14 -56.05(14) . . . . ?
O1 C7 N4 C8 -168.59(11) . . . . ?
O2 C13 N2 C8 173.31(11) . . . . ?
O2 C13 N2 C14 -1.08(18) . . . . ?
