#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:08:46 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272567 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/55/1565577.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_1565577
loop_
_publ_author_name
'Lin, Wei'
'Zhao, Qun'
'Li, Yao'
'Pan, Ming'
'Yang, Chen'
'Yang, Guo-Hui'
'Li, Xin'
_publ_section_title
;
 Asymmetric synthesis of N-N axially chiral compounds via
 organocatalytic atroposelective N-acylation.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              141
_journal_page_last               148
_journal_paper_doi               10.1039/d1sc05360d
_journal_volume                  13
_journal_year                    2021
_chemical_formula_moiety         'C30 H21 N3 O3'
_chemical_formula_sum            'C30 H21 N3 O3'
_chemical_formula_weight         471.50
_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             2020-11-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-19 deposited with the CCDC.	2021-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                114.3570(10)
_cell_angle_beta                 102.2220(10)
_cell_angle_gamma                94.5930(10)
_cell_formula_units_Z            2
_cell_length_a                   9.65870(10)
_cell_length_b                   11.53350(10)
_cell_length_c                   12.42160(10)
_cell_measurement_reflns_used    26402
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      78.5470
_cell_measurement_theta_min      4.0440
_cell_volume                     1210.05(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      294.15
_diffrn_detector                 Pilatus
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  94.00   0.50    0.50    --    5.00  57.00  90.00  238
  2  ω   -138.00 -15.00   0.50    0.50    --  -48.80 -69.00-138.82  246
  3  ω    -82.00  41.00   0.50    0.50    --  -48.80  38.00 -30.00  246
  4  ω    -79.00  41.00   0.50    0.50    --  -48.80  57.00  60.00  240
  5  ω   -138.00 -15.00   0.50    0.50    --  -48.80 -38.00-155.54  246
  6  ω   -138.00 -16.00   0.50    0.50    --  -48.80 -64.00 -35.91  244
  7  ω   -138.00 -18.00   0.50    0.50    --  -48.80 -57.00   0.00  240
  8  ω    -82.00  41.00   0.50    0.50    --  -48.80  71.00-172.52  246
  9  ω   -138.00 -16.00   0.50    0.50    --  -48.80 -64.00 -35.91  244
 10  ω   -199.00 -78.00   0.50    1.00    -- -110.00 -64.00 -29.40  242
 11  ω   -199.00 -78.00   0.50    1.00    -- -110.00 -40.00-125.08  242
 12  ω   -199.00 -76.00   0.50    1.00    -- -110.00 -72.00 140.96  246
 13  ω   -199.00 -79.00   0.50    1.00    -- -110.00 -44.00  48.28  240
 14  ω   -199.00 -79.00   0.50    1.00    -- -110.00 -61.00  79.14  240
 15  ω   -199.00 -79.00   0.50    1.00    -- -110.00 -61.00-172.28  240
 16  ω   -199.00 -77.00   0.50    1.00    -- -110.00 -70.00  53.04  244
 17  ω   -199.00 -77.00   0.50    1.00    -- -110.00 -71.00 130.48  244
 18  ω   -103.00 -77.00   0.50    1.00    -- -110.00 -68.00-116.12   52
 19  ω   -110.00 -76.00   0.50    1.00    -- -110.00 -72.00-168.79   68
 20  ω   -104.00 -78.00   0.50    1.00    -- -110.00 -64.00 154.75   52
 21  ω   -106.00 -78.00   0.50    1.00    -- -110.00 -42.00 138.62   56
 22  ω   -102.00 -77.00   0.50    1.00    -- -110.00 -68.00 -69.96   50
 23  ω   -198.00-119.00   0.50    1.00    -- -110.00 -68.00 -69.96  158
 24  ω   -167.00-141.00   0.50    1.00    -- -110.00 -42.00 138.62   52
 25  ω   -134.00 -79.00   0.50    1.00    -- -110.00 -43.00 -98.88  110
 26  ω   -117.00 -53.00   0.50    1.00    -- -110.00 -19.00 150.00  128
 27  ω   -118.00 -80.00   0.50    1.00    -- -110.00 -38.00  60.00   76
 28  ω   -103.00 -77.00   0.50    1.00    -- -110.00 -69.00-108.66   52
 29  ω   -106.00 -21.00   0.50    1.00    -- -110.00  72.00 -60.00  170
 30  ω   -197.00 -81.00   0.50    1.00    -- -110.00 -53.00 -39.00  232
 31  ω   -135.00 -78.00   0.50    1.00    -- -110.00  72.00 -90.00  114
 32  ω   -144.00 -54.00   0.50    1.00    -- -110.00  72.00  90.00  180
 33  ω   -130.00 -65.00   0.50    1.00    -- -110.00  72.00  30.00  130
 34  ω    -58.00 -22.00   0.50    1.00    -- -110.00  72.00  30.00   72
 35  ω   -120.00 -53.00   0.50    1.00    -- -110.00 -19.00  90.00  134
 36  ω   -142.00 -21.00   0.50    1.00    -- -110.00  72.00-150.00  242
 37  ω   -102.00 -76.00   0.50    1.00    -- -110.00 -72.00-150.00   52
 38  ω   -127.00 -80.00   0.50    1.00    -- -110.00 -57.00-120.00   94
 39  ω   -104.00 -77.00   0.50    1.00    -- -110.00 -71.00 107.35   54
 40  ω   -102.00 -76.00   0.50    1.00    -- -110.00 -72.00  60.00   52
 41  ω   -199.00 -76.00   0.50    1.00    -- -110.00 -72.00 120.00  246
 42  ω   -102.00 -76.00   0.50    1.00    -- -110.00 -72.00-120.00   52
 43  ω   -198.00-135.00   0.50    1.00    -- -110.00 -65.00   7.28  126
 44  ω   -105.00 -78.00   0.50    1.00    -- -110.00 -65.00   7.28   54
 45  ω   -101.00 -76.00   0.50    1.00    -- -110.00 -72.00-180.00   50
 46  ω   -107.00 -80.00   0.50    1.00    -- -110.00 -56.00 -47.18   54
 47  ω   -185.00-129.00   0.50    1.00    -- -110.00 -72.00 -90.00  112
 48  ω   -101.00 -76.00   0.50    1.00    -- -110.00 -72.00 -90.00   50
 49  ω   -199.00-116.00   0.50    1.00    -- -110.00 -72.00   0.00  166
 50  ω   -110.00 -77.00   0.50    1.00    -- -110.00 -72.00   0.00   66
 51  ω   -101.00 -76.00   0.50    1.00    -- -110.00 -72.00 150.00   50
 52  ω   -199.00-174.00   0.50    1.00    -- -110.00 -69.00-108.66   50
 53  ω   -101.00 -76.00   0.50    1.00    -- -110.00 -72.00 -44.96   50
 54  ω   -107.00 -80.00   0.50    1.00    -- -110.00 -45.00 -30.66   54
 55  ω   -104.00 -78.00   0.50    1.00    -- -110.00 -64.00-154.35   52
 56  ω   -101.00 -76.00   0.50    1.00    -- -110.00 -72.00  40.28   50
 57  ω   -112.00 -76.00   0.50    1.00    -- -110.00 -72.00-132.09   72
 58  ω   -110.00 -77.00   0.50    1.00    -- -110.00 -38.00-120.00   66
 59  ω   -103.00 -77.00   0.50    1.00    -- -110.00 -71.00 -52.48   52
 60  ω   -113.00 -80.00   0.50    1.00    -- -110.00 -51.00-160.12   66
 61  ω   -184.00-141.00   0.50    1.00    -- -110.00 -51.00-160.12   86
 62  ω   -197.00-111.00   0.50    1.00    -- -110.00 -72.00  40.28  172
 63  ω   -176.00-151.00   0.50    1.00    -- -110.00 -38.00  60.00   50
 64  ω   -172.00 -80.00   0.50    1.00    -- -110.00 -51.00  46.45  184
 65  ω   -103.00 -77.00   0.50    1.00    -- -110.00 -72.00 -30.00   52
 66  ω   -103.00 -82.50   0.50    1.00    -- -110.00 -70.00  82.11   41
 67  ω   -106.00 -80.00   0.50    1.00    -- -110.00 -57.00 -30.00   52
 68  ω   -106.00 -80.00   0.50    1.00    -- -110.00 -49.00   3.97   52
 69  ω   -105.00 -80.00   0.50    1.00    -- -110.00 -59.00 -95.54   50
 70  ω   -154.00-129.00   0.50    1.00    -- -110.00 -72.00-132.09   50
 71  ω   -122.00 -77.00   0.50    1.00    -- -110.00 -38.00 -90.00   90
 72  ω   -108.00 -79.00   0.50    1.00    -- -110.00 -62.00  12.00   58
 73  ω   -130.00 -72.00   0.50    1.00    -- -110.00  72.00   0.00  116
 74  ω   -191.00-165.00   0.50    1.00    -- -110.00 -43.00 -98.88   52
 75  ω   -106.00 -80.00   0.50    1.00    -- -110.00 -51.00  18.23   52
 76  ω   -108.00 -80.00   0.50    1.00    -- -110.00 -60.00  53.55   56
 77  ω   -106.00 -80.00   0.50    1.00    -- -110.00 -59.00  -8.94   52
 78  ω   -192.00-161.00   0.50    1.00    -- -110.00 -19.00  90.00   62
 79  ω   -155.00-130.00   0.50    1.00    -- -110.00 -19.00  90.00   50
 80  ω   -130.00 -72.00   0.50    1.00    -- -110.00 -29.00 -10.87  116
 81  ω   -179.00-153.00   0.50    1.00    -- -110.00 -29.00 -10.87   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Xtalab P200'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0405367000
_diffrn_orient_matrix_UB_12      -0.0503506000
_diffrn_orient_matrix_UB_13      0.0975075000
_diffrn_orient_matrix_UB_21      -0.0780832000
_diffrn_orient_matrix_UB_22      -0.1375867000
_diffrn_orient_matrix_UB_23      -0.0957591000
_diffrn_orient_matrix_UB_31      0.1409603000
_diffrn_orient_matrix_UB_32      -0.0286507000
_diffrn_orient_matrix_UB_33      -0.0361727000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            40355
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.155
_diffrn_reflns_theta_min         4.057
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0452
_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)+(0.0657P)²+0.1374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1240
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4726
_reflns_number_total             5058
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc05360d2.cif
_cod_data_source_block           p20201106a
_cod_depositor_comments          'Adding full bibliography for 1565577.cif.'
_cod_database_code               1565577
_shelx_shelxl_version_number     2018/3
_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   0.898
_shelx_estimated_absorpt_t_min   0.875
_reflns_odcompleteness_completeness 97.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23),
  C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
;
_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 4.631
_oxdiff_exptl_absorpt_empirical_full_min 0.700
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 -0.03183(10) 0.71543(10) 0.53540(10) 0.0739(3) Uani 1 1 d . . . . .
O2 O 0.26837(11) 0.54385(9) 0.53376(8) 0.0661(2) Uani 1 1 d . . . . .
O3 O 0.15522(11) 0.88823(9) 0.82453(8) 0.0689(2) Uani 1 1 d . . . . .
N1 N 0.35393(12) 0.88868(11) 0.53632(10) 0.0613(3) Uani 1 1 d . . . . .
N2 N 0.21164(10) 0.77783(9) 0.60812(9) 0.0528(2) Uani 1 1 d . . . . .
N3 N 0.20846(10) 0.71234(9) 0.68041(8) 0.0515(2) Uani 1 1 d . . . . .
C1 C 0.22724(15) 0.89272(12) 0.46061(11) 0.0585(3) Uani 1 1 d . . . . .
C2 C 0.23761(19) 0.95853(16) 0.38860(14) 0.0758(4) Uani 1 1 d . . . . .
H2 H 0.327312 0.998025 0.392066 0.091 Uiso 1 1 calc R . . . .
C3 C 0.1150(2) 0.96434(17) 0.31317(14) 0.0828(4) Uani 1 1 d . . . . .
H3 H 0.122428 1.008158 0.265762 0.099 Uiso 1 1 calc R . . . .
C4 C -0.0194(2) 0.90633(15) 0.30632(13) 0.0780(4) Uani 1 1 d . . . . .
H4 H -0.101191 0.910249 0.253705 0.094 Uiso 1 1 calc R . . . .
C5 C -0.03253(16) 0.84285(13) 0.37703(12) 0.0676(3) Uani 1 1 d . . . . .
H5 H -0.123107 0.804589 0.373108 0.081 Uiso 1 1 calc R . . . .
C6 C 0.09112(14) 0.83603(11) 0.45503(10) 0.0554(3) Uani 1 1 d . . . . .
C7 C 0.07854(13) 0.77070(11) 0.53165(11) 0.0555(3) Uani 1 1 d . . . . .
C8 C 0.34349(13) 0.83409(11) 0.60655(10) 0.0523(3) Uani 1 1 d . . . . .
C9 C 0.47658(13) 0.82921(12) 0.68882(11) 0.0541(3) Uani 1 1 d . . . . .
C10 C 0.50973(15) 0.90030(14) 0.81386(13) 0.0699(3) Uani 1 1 d . . . . .
H10 H 0.445163 0.948491 0.849687 0.084 Uiso 1 1 calc R . . . .
C11 C 0.64017(18) 0.89979(18) 0.88648(15) 0.0832(4) Uani 1 1 d . . . . .
H11 H 0.663608 0.948875 0.971119 0.100 Uiso 1 1 calc R . . . .
C12 C 0.73401(18) 0.8279(2) 0.83455(19) 0.0911(5) Uani 1 1 d . . . . .
H12 H 0.821301 0.827977 0.883695 0.109 Uiso 1 1 calc R . . . .
C13 C 0.7000(2) 0.7556(2) 0.7102(2) 0.1047(6) Uani 1 1 d . . . . .
H13 H 0.763960 0.706049 0.674837 0.126 Uiso 1 1 calc R . . . .
C14 C 0.57172(18) 0.75599(19) 0.63767(16) 0.0849(5) Uani 1 1 d . . . . .
H14 H 0.548857 0.706336 0.553131 0.102 Uiso 1 1 calc R . . . .
C15 C 0.25524(12) 0.59108(11) 0.63679(10) 0.0519(3) Uani 1 1 d . . . . .
C16 C 0.29791(13) 0.53928(11) 0.72640(10) 0.0537(3) Uani 1 1 d . . . . .
H16 H 0.292867 0.585197 0.806609 0.064 Uiso 1 1 calc R . . . .
C17 C 0.34326(15) 0.42814(12) 0.69373(12) 0.0610(3) Uani 1 1 d . . . . .
H17 H 0.344326 0.384788 0.612126 0.073 Uiso 1 1 calc R . . . .
C18 C 0.39213(15) 0.36598(12) 0.77292(12) 0.0600(3) Uani 1 1 d . . . . .
C19 C 0.4837(2) 0.27840(18) 0.74276(16) 0.0899(5) Uani 1 1 d . . . . .
H19 H 0.512057 0.257804 0.670993 0.108 Uiso 1 1 calc R . . . .
C20 C 0.5337(3) 0.2211(2) 0.8180(2) 0.1067(7) Uani 1 1 d . . . . .
H20 H 0.596922 0.163890 0.797457 0.128 Uiso 1 1 calc R . . . .
C21 C 0.4908(2) 0.24792(17) 0.92211(16) 0.0863(5) Uani 1 1 d . . . . .
H21 H 0.525524 0.209881 0.972888 0.104 Uiso 1 1 calc R . . . .
C22 C 0.39664(19) 0.33094(16) 0.95177(14) 0.0771(4) Uani 1 1 d . . . . .
H22 H 0.365137 0.347419 1.021540 0.093 Uiso 1 1 calc R . . . .
C23 C 0.34820(16) 0.39040(14) 0.87823(13) 0.0668(3) Uani 1 1 d . . . . .
H23 H 0.285199 0.447626 0.899737 0.080 Uiso 1 1 calc R . . . .
C24 C 0.14743(12) 0.77198(11) 0.77929(10) 0.0529(3) Uani 1 1 d . . . . .
C25 C 0.06840(13) 0.68682(12) 0.81749(10) 0.0535(3) Uani 1 1 d . . . . .
C26 C 0.07344(17) 0.73130(15) 0.94136(12) 0.0679(3) Uani 1 1 d . . . . .
H26 H 0.132958 0.809157 0.999488 0.081 Uiso 1 1 calc R . . . .
C27 C -0.0110(2) 0.65843(18) 0.97686(15) 0.0845(5) Uani 1 1 d . . . . .
H27 H -0.006774 0.686627 1.059451 0.101 Uiso 1 1 calc R . . . .
C28 C -0.1009(2) 0.54477(18) 0.89089(18) 0.0857(5) Uani 1 1 d . . . . .
H28 H -0.157950 0.496855 0.915541 0.103 Uiso 1 1 calc R . . . .
C29 C -0.10728(18) 0.50121(15) 0.76851(15) 0.0745(4) Uani 1 1 d . . . . .
H29 H -0.168972 0.424418 0.710701 0.089 Uiso 1 1 calc R . . . .
C30 C -0.02206(14) 0.57151(13) 0.73149(12) 0.0598(3) Uani 1 1 d . . . . .
H30 H -0.025382 0.541480 0.648886 0.072 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 0.0181 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
C8 N1 C1 118.11(11) . . ?
N3 N2 C7 115.99(9) . . ?
C8 N2 N3 119.57(9) . . ?
C8 N2 C7 124.13(10) . . ?
N2 N3 C15 114.96(9) . . ?
N2 N3 C24 114.39(9) . . ?
C24 N3 C15 130.38(9) . . ?
N1 C1 C2 118.30(13) . . ?
N1 C1 C6 122.76(11) . . ?
C6 C1 C2 118.93(13) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.75(16) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.19(14) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.16(14) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.66(14) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 120.30(12) . . ?
C1 C6 C7 119.50(11) . . ?
C5 C6 C7 120.20(12) . . ?
O1 C7 N2 120.13(11) . . ?
O1 C7 C6 126.97(11) . . ?
N2 C7 C6 112.89(10) . . ?
N1 C8 N2 122.50(11) . . ?
N1 C8 C9 119.27(11) . . ?
N2 C8 C9 118.23(10) . . ?
C10 C9 C8 121.62(12) . . ?
C10 C9 C14 119.42(13) . . ?
C14 C9 C8 118.89(12) . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.58(14) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.38(16) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.03(15) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.01(17) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.56(16) . . ?
C13 C14 H14 119.7 . . ?
O2 C15 N3 118.61(10) . . ?
O2 C15 C16 124.58(11) . . ?
N3 C15 C16 116.52(9) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.36(11) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 116.7 . . ?
C16 C17 C18 126.58(12) . . ?
C18 C17 H17 116.7 . . ?
C19 C18 C17 120.05(12) . . ?
C19 C18 C23 117.80(13) . . ?
C23 C18 C17 122.14(12) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.82(15) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.39(16) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.85(15) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.12(15) . . ?
C23 C22 H22 119.9 . . ?
C18 C23 H23 119.5 . . ?
C22 C23 C18 120.96(14) . . ?
C22 C23 H23 119.5 . . ?
O3 C24 N3 119.35(11) . . ?
O3 C24 C25 122.85(11) . . ?
N3 C24 C25 117.69(10) . . ?
C26 C25 C24 118.68(12) . . ?
C30 C25 C24 121.09(10) . . ?
C30 C25 C26 119.84(12) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 C25 119.33(14) . . ?
C27 C26 H26 120.3 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.37(14) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 119.8 . . ?
C27 C28 C29 120.47(14) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 120.0 . . ?
C28 C29 C30 120.01(15) . . ?
C30 C29 H29 120.0 . . ?
C25 C30 H30 120.0 . . ?
C29 C30 C25 119.96(12) . . ?
C29 C30 H30 120.0 . . ?
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 1.2172(15) . ?
O2 C15 1.2063(14) . ?
O3 C24 1.2098(15) . ?
N1 C1 1.3936(17) . ?
N1 C8 1.2837(15) . ?
N2 N3 1.3948(12) . ?
N2 C7 1.4012(15) . ?
N2 C8 1.3899(15) . ?
N3 C15 1.4260(15) . ?
N3 C24 1.4156(15) . ?
C1 C2 1.4042(18) . ?
C1 C6 1.3954(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.3997(18) . ?
C6 C7 1.4541(16) . ?
C8 C9 1.4842(16) . ?
C9 C10 1.3727(19) . ?
C9 C14 1.375(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.388(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.361(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.366(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.371(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.4696(16) . ?
C16 H16 0.9300 . ?
C16 C17 1.3175(17) . ?
C17 H17 0.9300 . ?
C17 C18 1.4640(18) . ?
C18 C19 1.384(2) . ?
C18 C23 1.3860(19) . ?
C19 H19 0.9300 . ?
C19 C20 1.384(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.362(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.368(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.382(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.4799(17) . ?
C25 C26 1.3951(17) . ?
C25 C30 1.3857(18) . ?
C26 H26 0.9300 . ?
C26 C27 1.383(2) . ?
C27 H27 0.9300 . ?
C27 C28 1.372(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.376(2) . ?
C29 H29 0.9300 . ?
C29 C30 1.3810(19) . ?
C30 H30 0.9300 . ?
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
O2 C15 C16 C17 -5.93(19) . . . . ?
O3 C24 C25 C26 -37.47(17) . . . . ?
O3 C24 C25 C30 135.35(13) . . . . ?
N1 C1 C2 C3 -179.97(13) . . . . ?
N1 C1 C6 C5 -179.86(12) . . . . ?
N1 C1 C6 C7 0.65(18) . . . . ?
N1 C8 C9 C10 110.57(15) . . . . ?
N1 C8 C9 C14 -66.51(17) . . . . ?
N2 N3 C15 O2 -13.04(15) . . . . ?
N2 N3 C15 C16 161.03(9) . . . . ?
N2 N3 C24 O3 -28.59(15) . . . . ?
N2 N3 C24 C25 147.67(10) . . . . ?
N2 C8 C9 C10 -69.97(16) . . . . ?
N2 C8 C9 C14 112.95(15) . . . . ?
N3 N2 C7 O1 3.64(17) . . . . ?
N3 N2 C7 C6 -177.31(9) . . . . ?
N3 N2 C8 N1 175.62(11) . . . . ?
N3 N2 C8 C9 -3.82(15) . . . . ?
N3 C15 C16 C17 -179.60(11) . . . . ?
N3 C24 C25 C26 146.42(11) . . . . ?
N3 C24 C25 C30 -40.77(16) . . . . ?
C1 N1 C8 N2 0.99(18) . . . . ?
C1 N1 C8 C9 -179.57(10) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C1 C6 C7 O1 -178.78(13) . . . . ?
C1 C6 C7 N2 2.24(16) . . . . ?
C2 C1 C6 C5 1.19(19) . . . . ?
C2 C1 C6 C7 -178.30(12) . . . . ?
C2 C3 C4 C5 0.9(2) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C4 C5 C6 C7 179.13(12) . . . . ?
C5 C6 C7 O1 1.7(2) . . . . ?
C5 C6 C7 N2 -177.25(11) . . . . ?
C6 C1 C2 C3 -1.0(2) . . . . ?
C7 N2 N3 C15 102.25(11) . . . . ?
C7 N2 N3 C24 -72.53(13) . . . . ?
C7 N2 C8 N1 2.26(18) . . . . ?
C7 N2 C8 C9 -177.18(10) . . . . ?
C8 N1 C1 C2 176.56(12) . . . . ?
C8 N1 C1 C6 -2.39(19) . . . . ?
C8 N2 N3 C15 -71.64(13) . . . . ?
C8 N2 N3 C24 113.58(11) . . . . ?
C8 N2 C7 O1 177.21(11) . . . . ?
C8 N2 C7 C6 -3.74(16) . . . . ?
C8 C9 C10 C11 -175.47(13) . . . . ?
C8 C9 C14 C13 175.88(17) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C10 C9 C14 C13 -1.3(3) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 C9 0.3(3) . . . . ?
C14 C9 C10 C11 1.6(2) . . . . ?
C15 N3 C24 O3 157.63(11) . . . . ?
C15 N3 C24 C25 -26.12(17) . . . . ?
C15 C16 C17 C18 178.56(12) . . . . ?
C16 C17 C18 C19 -156.29(17) . . . . ?
C16 C17 C18 C23 24.6(2) . . . . ?
C17 C18 C19 C20 178.46(18) . . . . ?
C17 C18 C23 C22 -179.63(14) . . . . ?
C18 C19 C20 C21 1.4(4) . . . . ?
C19 C18 C23 C22 1.2(2) . . . . ?
C19 C20 C21 C22 0.7(3) . . . . ?
C20 C21 C22 C23 -1.8(3) . . . . ?
C21 C22 C23 C18 0.9(2) . . . . ?
C23 C18 C19 C20 -2.4(3) . . . . ?
C24 N3 C15 O2 160.71(11) . . . . ?
C24 N3 C15 C16 -25.22(17) . . . . ?
C24 C25 C26 C27 173.73(13) . . . . ?
C24 C25 C30 C29 -172.50(12) . . . . ?
C25 C26 C27 C28 -1.3(2) . . . . ?
C26 C25 C30 C29 0.2(2) . . . . ?
C26 C27 C28 C29 0.6(3) . . . . ?
C27 C28 C29 C30 0.5(3) . . . . ?
C28 C29 C30 C25 -0.9(2) . . . . ?
C30 C25 C26 C27 0.8(2) . . . . ?
