#------------------------------------------------------------------------------
#$Date: 2022-03-05 00:24:00 +0200 (Sat, 05 Mar 2022) $
#$Revision: 273419 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/84/7158494.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_7158494
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         'C21 H20 N4 O'
_chemical_formula_sum            'C21 H20 N4 O'
_chemical_formula_weight         344.41
_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                 105.285(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5402(3)
_cell_length_b                   7.8769(2)
_cell_length_c                   16.4206(4)
_cell_measurement_reflns_used    10013
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1340
_cell_measurement_theta_min      3.8040
_cell_volume                     1689.38(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.23a (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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00 -49.00   0.50    0.15    --  -47.48 -74.00 144.00  136
  2  ω    -47.00   6.00   0.50    0.15    --  -47.48  74.00 -87.00  106
  3  ω    -10.00  72.00   0.50    0.15    --   47.48 -74.00 144.00  164
  4  ω   -164.00 -66.00   0.50    0.58    --  -90.25 -74.00 144.00  196
  5  ω     47.00  89.00   0.50    0.58    --  101.53 -74.00 144.00   84
  6  ω    133.00 177.00   0.50    0.58    --  101.53  74.00 -87.00   88
  7  ω     86.00 123.00   0.50    0.58    --  101.53  74.00 -87.00   74
  8  ω   -124.00 -71.00   0.50    0.15    --  -47.48-125.00  90.00  106
  9  ω   -124.00 -70.00   0.50    0.15    --  -47.48-125.00-150.00  108
 10  ω     40.00 121.00   0.50    0.15    --   47.48  57.00 -30.00  162
 11  ω    -10.00  28.00   0.50    0.15    --   47.48 -38.00 150.00   76
 12  ω    -87.00 -11.00   0.50    0.58    --  -90.25 111.00 -90.00  152
 13  ω   -153.00 -91.00   0.50    0.58    --  -90.25 -61.00   0.00  124
 14  ω   -127.00-100.00   0.50    0.58    --  -90.25 -94.00  60.00   54
 15  ω   -117.00 -71.00   0.50    0.58    --  -90.25 -30.00  30.00   92
 16  ω    -91.00 -65.00   0.50    0.58    --  -90.25  74.00 -87.00   52
 17  ω   -159.00-112.00   0.50    0.58    --  -90.25 -77.00  90.00   94
 18  ω    -82.00 -37.00   0.50    0.58    --  -90.25  61.00 120.00   90
 19  ω     86.00 174.00   0.50    0.58    --  101.53  30.00  60.00  176
 20  ω     82.00 176.00   0.50    0.58    --  101.53  45.00-120.00  188
 21  ω    124.00 172.00   0.50    0.58    --  101.53  77.00-180.00   96
 22  ω     25.00 111.00   0.50    0.58    --  101.53-111.00 120.00  172
 23  ω     82.00 110.00   0.50    0.58    --  101.53  77.00-180.00   56
 24  ω     82.00 111.00   0.50    0.58    --  101.53  30.00-150.00   58
 25  ω    129.00 176.00   0.50    0.58    --  101.53 111.00  30.00   94
 26  ω     95.00 120.00   0.50    0.58    --  101.53 -61.00  30.00   50
 27  ω     42.00  75.00   0.50    0.58    --  101.53 -61.00  30.00   66
 28  ω     25.00  90.00   0.50    0.58    --  101.53 -45.00 150.00  130
 29  ω     85.00 147.00   0.50    0.58    --  101.53  30.00   0.00  124
 30  ω     37.00 122.00   0.50    0.58    --  101.53 -61.00 150.00  170
 31  ω     91.00 158.00   0.50    0.58    --  101.53  61.00   0.00  134
 32  ω    121.00 164.00   0.50    0.58    --  101.53  30.00-150.00   86
;
_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      0.0521524000
_diffrn_orient_matrix_UB_12      0.1412104000
_diffrn_orient_matrix_UB_13      0.0613497000
_diffrn_orient_matrix_UB_21      0.0440204000
_diffrn_orient_matrix_UB_22      0.0765975000
_diffrn_orient_matrix_UB_23      -0.0692766000
_diffrn_orient_matrix_UB_31      -0.0962085000
_diffrn_orient_matrix_UB_32      0.1116198000
_diffrn_orient_matrix_UB_33      -0.0298339000
_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  0.0602
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19105
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.673
_diffrn_reflns_theta_max         67.673
_diffrn_reflns_theta_min         3.776
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.23a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0447
_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)+(0.0808P)²+0.5055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2822
_reflns_number_total             3053
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob02372a2.cif
_cod_data_source_block           jls_37_1
_cod_depositor_comments
'Adding full bibliography for 7158492--7158494.cif.'
_cod_database_code               7158494
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C21H20N4O
_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   0.993
_shelx_estimated_absorpt_t_min   0.967
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C18(H18), C19(H19), C20(H20), N3(H3A)
;
_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 1.403
_oxdiff_exptl_absorpt_empirical_full_min 0.695
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 0.24868(10) 0.16102(17) 0.59926(9) 0.0196(3) Uani 1 1 d . . . . .
C2 C 0.19900(11) 0.18311(17) 0.51433(9) 0.0223(3) Uani 1 1 d . . . . .
H2 H 0.127984 0.179295 0.495192 0.027 Uiso 1 1 calc R U . . .
C3 C 0.25919(11) 0.21101(18) 0.45928(9) 0.0245(3) Uani 1 1 d . . . . .
H3 H 0.228139 0.228015 0.402223 0.029 Uiso 1 1 calc R U . . .
C4 C 0.36675(11) 0.21399(18) 0.48849(9) 0.0254(3) Uani 1 1 d . . . . .
H4 H 0.405471 0.232413 0.450210 0.030 Uiso 1 1 calc R U . . .
C5 C 0.41583(11) 0.19023(18) 0.57246(9) 0.0230(3) Uani 1 1 d . . . . .
H5 H 0.486941 0.191186 0.590689 0.028 Uiso 1 1 calc R U . . .
C6 C 0.35685(10) 0.16445(17) 0.63042(9) 0.0199(3) Uani 1 1 d . . . . .
C7 C 0.37876(10) 0.13787(16) 0.72001(9) 0.0192(3) Uani 1 1 d . . . . .
C8 C 0.28719(10) 0.11982(17) 0.73930(8) 0.0180(3) Uani 1 1 d . . . . .
C9 C 0.27218(9) 0.08047(17) 0.82477(8) 0.0185(3) Uani 1 1 d . . . . .
H9 H 0.235420 -0.027751 0.820173 0.022 Uiso 1 1 calc R U . . .
C10 C 0.47813(10) 0.12817(18) 0.78667(9) 0.0217(3) Uani 1 1 d . . . . .
H10A H 0.525144 0.213279 0.776294 0.026 Uiso 1 1 calc R U . . .
H10B H 0.508920 0.017250 0.785694 0.026 Uiso 1 1 calc R U . . .
C11 C 0.45744(10) 0.15880(18) 0.87264(9) 0.0218(3) Uani 1 1 d . . . . .
H11A H 0.519137 0.132985 0.916513 0.026 Uiso 1 1 calc R U . . .
H11B H 0.442268 0.278183 0.877367 0.026 Uiso 1 1 calc R U . . .
C12 C 0.20659(10) 0.21463(17) 0.85413(8) 0.0195(3) Uani 1 1 d . . . . .
H12A H 0.147120 0.239267 0.807854 0.023 Uiso 1 1 calc R U . . .
H12B H 0.246082 0.318447 0.867485 0.023 Uiso 1 1 calc R U . . .
C13 C 0.16992(10) 0.16121(19) 0.93192(9) 0.0221(3) Uani 1 1 d . . . . .
H13A H 0.099789 0.198936 0.923752 0.026 Uiso 1 1 calc R U . . .
H13B H 0.170048 0.038228 0.934995 0.026 Uiso 1 1 calc R U . . .
C14 C 0.23303(10) 0.22954(17) 1.01466(9) 0.0197(3) Uani 1 1 d . . . . .
C15 C 0.40670(10) 0.28104(17) 1.09748(9) 0.0198(3) Uani 1 1 d . . . . .
C16 C 0.36069(10) 0.35440(16) 1.16055(9) 0.0200(3) Uani 1 1 d . . . . .
C17 C 0.42090(11) 0.41811(18) 1.23705(9) 0.0241(3) Uani 1 1 d . . . . .
H17 H 0.491796 0.419740 1.247315 0.029 Uiso 1 1 calc R U . . .
C18 C 0.37572(11) 0.47853(19) 1.29737(9) 0.0262(3) Uani 1 1 d . . . . .
H18 H 0.415725 0.518901 1.348726 0.031 Uiso 1 1 calc R U . . .
C19 C 0.26842(11) 0.47828(18) 1.28017(9) 0.0256(3) Uani 1 1 d . . . . .
H19 H 0.237649 0.517851 1.320899 0.031 Uiso 1 1 calc R U . . .
C20 C 0.20856(11) 0.42114(18) 1.20493(9) 0.0240(3) Uani 1 1 d . . . . .
H20 H 0.137666 0.425123 1.194406 0.029 Uiso 1 1 calc R U . . .
C21 C 0.25323(10) 0.35587(17) 1.14276(9) 0.0204(3) Uani 1 1 d . . . . .
N1 N 0.20774(9) 0.13304(14) 0.66706(7) 0.0191(3) Uani 1 1 d . . . . .
N2 N 0.37219(8) 0.05715(15) 0.88753(7) 0.0197(3) Uani 1 1 d . . . . .
N3 N 0.33747(8) 0.21653(14) 1.02851(7) 0.0198(3) Uani 1 1 d . . . . .
H3A H 0.360557 0.164431 0.991325 0.024 Uiso 1 1 calc R U . . .
N4 N 0.18893(8) 0.29538(15) 1.06844(7) 0.0213(3) Uani 1 1 d . . . . .
O O 0.50018(7) 0.27261(13) 1.10454(6) 0.0243(3) Uani 1 1 d . . . . .
H2A H 0.3909(13) -0.049(2) 0.8908(10) 0.023(4) Uiso 1 1 d . . . . .
H1 H 0.1389(16) 0.137(3) 0.6627(12) 0.036(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
C2 C1 C6 122.68(12) . . ?
N1 C1 C2 129.46(12) . . ?
N1 C1 C6 107.87(12) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 C1 117.53(13) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.93(13) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.45(13) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.10(13) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 106.34(12) . . ?
C5 C6 C1 118.31(13) . . ?
C5 C6 C7 135.36(13) . . ?
C6 C7 C10 131.26(12) . . ?
C8 C7 C6 107.31(12) . . ?
C8 C7 C10 121.43(12) . . ?
C7 C8 C9 126.35(12) . . ?
C7 C8 N1 110.04(12) . . ?
N1 C8 C9 123.51(11) . . ?
C8 C9 H9 107.4 . . ?
C8 C9 C12 112.50(11) . . ?
C12 C9 H9 107.4 . . ?
N2 C9 C8 110.58(10) . . ?
N2 C9 H9 107.4 . . ?
N2 C9 C12 111.40(11) . . ?
C7 C10 H10A 110.0 . . ?
C7 C10 H10B 110.0 . . ?
C7 C10 C11 108.61(11) . . ?
H10A C10 H10B 108.3 . . ?
C11 C10 H10A 110.0 . . ?
C11 C10 H10B 110.0 . . ?
C10 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
N2 C11 C10 114.12(11) . . ?
N2 C11 H11A 108.7 . . ?
N2 C11 H11B 108.7 . . ?
C9 C12 H12A 108.7 . . ?
C9 C12 H12B 108.7 . . ?
C9 C12 C13 114.20(11) . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C12 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.5 . . ?
C14 C13 C12 114.84(11) . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
N3 C14 C13 115.97(11) . . ?
N4 C14 C13 120.33(12) . . ?
N4 C14 N3 123.70(13) . . ?
N3 C15 C16 114.07(12) . . ?
O C15 C16 124.71(13) . . ?
O C15 N3 121.21(12) . . ?
C17 C16 C15 121.49(12) . . ?
C17 C16 C21 120.65(12) . . ?
C21 C16 C15 117.84(12) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.36(13) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.5 . . ?
C17 C18 C19 119.09(13) . . ?
C19 C18 H18 120.5 . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.25(13) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.63(13) . . ?
C21 C20 H20 119.7 . . ?
C16 C21 C20 117.98(13) . . ?
N4 C21 C16 123.80(12) . . ?
N4 C21 C20 118.22(12) . . ?
C1 N1 H1 123.1(12) . . ?
C8 N1 C1 108.45(11) . . ?
C8 N1 H1 128.0(12) . . ?
C9 N2 H2A 111.0(11) . . ?
C11 N2 C9 115.38(11) . . ?
C11 N2 H2A 107.7(11) . . ?
C14 N3 H3A 117.9 . . ?
C15 N3 C14 124.13(11) . . ?
C15 N3 H3A 117.9 . . ?
C14 N4 C21 116.26(11) . . ?
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 C2 1.390(2) . ?
C1 C6 1.4186(19) . ?
C1 N1 1.3859(17) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.408(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.4091(19) . ?
C6 C7 1.4374(19) . ?
C7 C8 1.3655(18) . ?
C7 C10 1.4959(19) . ?
C8 C9 1.5026(17) . ?
C8 N1 1.3792(18) . ?
C9 H9 0.9800 . ?
C9 C12 1.5374(18) . ?
C9 N2 1.4811(17) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.5291(18) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 N2 1.4772(17) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.5459(18) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.5012(19) . ?
C14 N3 1.3757(17) . ?
C14 N4 1.2973(18) . ?
C15 C16 1.4611(18) . ?
C15 N3 1.3637(18) . ?
C15 O 1.2420(16) . ?
C16 C17 1.398(2) . ?
C16 C21 1.4066(19) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.405(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.363(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.4135(19) . ?
C21 N4 1.3836(18) . ?
N1 H1 0.92(2) . ?
N2 H2A 0.874(19) . ?
N3 H3A 0.8600 . ?
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 1.0(2) . . . . ?
C1 C6 C7 C8 0.06(15) . . . . ?
C1 C6 C7 C10 179.84(13) . . . . ?
C2 C1 C6 C5 -0.4(2) . . . . ?
C2 C1 C6 C7 179.80(12) . . . . ?
C2 C1 N1 C8 -179.73(13) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C4 C5 C6 C1 1.1(2) . . . . ?
C4 C5 C6 C7 -179.19(15) . . . . ?
C5 C6 C7 C8 -179.65(15) . . . . ?
C5 C6 C7 C10 0.1(3) . . . . ?
C6 C1 C2 C3 -0.6(2) . . . . ?
C6 C1 N1 C8 0.27(14) . . . . ?
C6 C7 C8 C9 176.54(12) . . . . ?
C6 C7 C8 N1 0.11(15) . . . . ?
C6 C7 C10 C11 160.82(14) . . . . ?
C7 C8 C9 C12 123.36(14) . . . . ?
C7 C8 C9 N2 -1.91(19) . . . . ?
C7 C8 N1 C1 -0.24(15) . . . . ?
C7 C10 C11 N2 48.52(16) . . . . ?
C8 C7 C10 C11 -19.43(18) . . . . ?
C8 C9 C12 C13 167.63(11) . . . . ?
C8 C9 N2 C11 31.51(15) . . . . ?
C9 C8 N1 C1 -176.80(12) . . . . ?
C9 C12 C13 C14 98.34(14) . . . . ?
C10 C7 C8 C9 -3.3(2) . . . . ?
C10 C7 C8 N1 -179.70(12) . . . . ?
C10 C11 N2 C9 -57.63(16) . . . . ?
C12 C9 N2 C11 -94.38(13) . . . . ?
C12 C13 C14 N3 -45.95(17) . . . . ?
C12 C13 C14 N4 134.31(13) . . . . ?
C13 C14 N3 C15 175.74(12) . . . . ?
C13 C14 N4 C21 -179.66(12) . . . . ?
C15 C16 C17 C18 -176.59(13) . . . . ?
C15 C16 C21 C20 177.75(12) . . . . ?
C15 C16 C21 N4 -1.5(2) . . . . ?
C16 C15 N3 C14 4.96(19) . . . . ?
C16 C17 C18 C19 -1.3(2) . . . . ?
C16 C21 N4 C14 2.2(2) . . . . ?
C17 C16 C21 C20 -0.9(2) . . . . ?
C17 C16 C21 N4 179.86(13) . . . . ?
C17 C18 C19 C20 -0.6(2) . . . . ?
C18 C19 C20 C21 1.8(2) . . . . ?
C19 C20 C21 C16 -1.0(2) . . . . ?
C19 C20 C21 N4 178.29(13) . . . . ?
C20 C21 N4 C14 -176.97(12) . . . . ?
C21 C16 C17 C18 2.0(2) . . . . ?
N1 C1 C2 C3 179.37(13) . . . . ?
N1 C1 C6 C5 179.56(12) . . . . ?
N1 C1 C6 C7 -0.20(14) . . . . ?
N1 C8 C9 C12 -60.65(16) . . . . ?
N1 C8 C9 N2 174.08(12) . . . . ?
N2 C9 C12 C13 -67.54(14) . . . . ?
N3 C14 N4 C21 0.6(2) . . . . ?
N3 C15 C16 C17 176.63(12) . . . . ?
N3 C15 C16 C21 -2.05(18) . . . . ?
N4 C14 N3 C15 -4.5(2) . . . . ?
O C15 C16 C17 -1.9(2) . . . . ?
O C15 C16 C21 179.40(12) . . . . ?
O C15 N3 C14 -176.43(12) . . . . ?
