#------------------------------------------------------------------------------
#$Date: 2024-05-05 03:54:26 +0200 (Sun 05 de May de 2024) $
#$Revision: 291578 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/12/1571248.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_1571248
loop_
_publ_author_name
'Ma, Foqing'
'Li, Yunlong'
'Akkarasereenon, Kornkamon'
'Qiu, Huiying'
'Cheung, Yuen Tsz'
'Guo, Zhihong'
'Tong, Rongbiao'
_publ_section_title
;
 Aza-Achmatowicz rearrangement coupled with intermolecular
 aza-Friedel-Crafts enables total syntheses of uleine and aspidosperma
 alkaloids.
;
_journal_issue                   15
_journal_name_full               'Chemical science'
_journal_page_first              5730
_journal_page_last               5737
_journal_paper_doi               10.1039/d4sc00601a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C18 H22 N2 O3'
_chemical_formula_sum            'C18 H22 N2 O3'
_chemical_formula_weight         314.37
_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     iterative
_audit_creation_date             2021-08-26
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6392)
;
_audit_update_record
;
2023-10-04 deposited with the CCDC.	2024-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                83.313(5)
_cell_angle_beta                 81.185(5)
_cell_angle_gamma                61.479(6)
_cell_formula_units_Z            2
_cell_length_a                   8.9869(6)
_cell_length_b                   9.3453(5)
_cell_length_c                   11.1740(6)
_cell_measurement_reflns_used    3096
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.3310
_cell_measurement_theta_min      4.0010
_cell_volume                     813.81(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1788
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     92.00 176.00   1.00    3.00    --  113.00  30.00   0.00   84
  2  ω    -59.00  -7.00   1.00    1.50    --  -39.95 125.00-120.00   52
  3  ω   -116.00 -16.00   1.00    1.50    --  -39.95 -37.00  60.00  100
  4  ω   -113.00 -28.00   1.00    1.50    --  -39.95 -37.00 -30.00   85
  5  ω    -77.00  -6.00   1.00    1.50    --  -39.95 125.00 150.00   71
  6  ω     53.00  97.00   1.00    1.50    --   39.95-125.00  60.00   44
  7  ω     36.00 108.00   1.00    3.00    --  113.00-111.00  30.00   72
  8  ω    104.00 176.00   1.00    3.00    --  113.00 111.00-180.00   72
  9  ω     64.00 109.00   1.00    3.00    --  113.00-111.00 120.00   45
 10  ω     36.00  63.00   1.00    3.00    --  113.00-111.00 120.00   27
 11  ω     35.00 107.00   1.00    3.00    --  113.00 -94.00-150.00   72
 12  ω     85.00 168.00   1.00    3.00    --  113.00  45.00 -60.00   83
 13  ω     85.00 177.00   1.00    3.00    --  113.00  45.00-120.00   92
 14  ω     47.00 138.00   1.00    3.00    --  113.00 -61.00-150.00   91
 15  ω     51.00 122.00   1.00    3.00    --  113.00 -45.00  60.00   71
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1375284000
_diffrn_orient_matrix_UB_12      -0.1658001000
_diffrn_orient_matrix_UB_13      0.0460295000
_diffrn_orient_matrix_UB_21      -0.0235061000
_diffrn_orient_matrix_UB_22      0.0712600000
_diffrn_orient_matrix_UB_23      0.1232025000
_diffrn_orient_matrix_UB_31      -0.1381294000
_diffrn_orient_matrix_UB_32      -0.0521614000
_diffrn_orient_matrix_UB_33      0.0470785000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5008
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.729
_diffrn_reflns_theta_min         4.008
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3272
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0346
_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)+(0.0441P)²+0.2115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0907
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2924
_reflns_number_total             3272
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc00601a1.cif
_cod_data_source_block           fma4cult_auto
_cod_depositor_comments
'Adding full bibliography for 1571247--1571248.cif.'
_cod_database_code               1571248
_shelx_shelxl_version_number     2014/7
_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   0.932
_shelx_estimated_absorpt_t_min   0.901
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 1.408
_oxdiff_exptl_absorpt_empirical_full_min 0.831
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 -0.15576(10) 0.61474(11) 0.33088(7) 0.0231(2) Uani 1 1 d . . . . .
H1 H -0.2154 0.6526 0.3963 0.035 Uiso 1 1 calc R U . . .
O2 O 0.37109(10) 0.26016(10) 0.46919(7) 0.01991(18) Uani 1 1 d . . . . .
O3 O 0.56940(10) 0.30096(10) 0.33853(7) 0.01763(18) Uani 1 1 d . . . . .
N1 N 0.31013(11) 0.38651(12) 0.28331(8) 0.0159(2) Uani 1 1 d . . . . .
N2 N 0.31821(13) 0.34320(13) -0.11837(9) 0.0230(2) Uani 1 1 d . . . . .
H2 H 0.2680 0.3545 -0.1831 0.028 Uiso 1 1 calc R U . . .
C1 C 0.13572(14) 0.41099(14) 0.30507(10) 0.0172(2) Uani 1 1 d . . . . .
H1A H 0.1261 0.3367 0.3730 0.021 Uiso 1 1 calc R U . . .
H1B H 0.1049 0.3855 0.2319 0.021 Uiso 1 1 calc R U . . .
C2 C 0.01440(14) 0.58681(14) 0.33571(10) 0.0178(2) Uani 1 1 d . . . . .
H2A H 0.0271 0.6052 0.4191 0.021 Uiso 1 1 calc R U . . .
C3 C 0.05588(15) 0.69857(14) 0.24483(10) 0.0194(2) Uani 1 1 d . . . . .
H3 H -0.0267 0.8101 0.2388 0.023 Uiso 1 1 calc R U . . .
C4 C 0.20162(14) 0.64961(14) 0.17268(10) 0.0182(2) Uani 1 1 d . . . . .
H4 H 0.2165 0.7279 0.1170 0.022 Uiso 1 1 calc R U . . .
C5 C 0.34493(13) 0.47687(14) 0.17402(10) 0.0160(2) Uani 1 1 d . . . . .
H5 H 0.4531 0.4802 0.1801 0.019 Uiso 1 1 calc R U . . .
C6 C 0.41382(14) 0.31293(13) 0.37130(10) 0.0155(2) Uani 1 1 d . . . . .
C7 C 0.70865(14) 0.20394(14) 0.41568(10) 0.0191(2) Uani 1 1 d . . . . .
C8 C 0.67622(17) 0.29117(16) 0.53054(12) 0.0279(3) Uani 1 1 d . . . . .
H8A H 0.6656 0.4001 0.5093 0.042 Uiso 1 1 calc R U . . .
H8B H 0.7715 0.2288 0.5792 0.042 Uiso 1 1 calc R U . . .
H8C H 0.5706 0.3010 0.5775 0.042 Uiso 1 1 calc R U . . .
C9 C 0.72914(15) 0.03220(15) 0.44162(12) 0.0245(3) Uani 1 1 d . . . . .
H9A H 0.6413 0.0338 0.5061 0.037 Uiso 1 1 calc R U . . .
H9B H 0.8421 -0.0404 0.4674 0.037 Uiso 1 1 calc R U . . .
H9C H 0.7172 -0.0073 0.3680 0.037 Uiso 1 1 calc R U . . .
C10 C 0.86213(15) 0.20159(17) 0.33433(12) 0.0275(3) Uani 1 1 d . . . . .
H10A H 0.8801 0.1455 0.2605 0.041 Uiso 1 1 calc R U . . .
H10B H 0.9636 0.1440 0.3776 0.041 Uiso 1 1 calc R U . . .
H10C H 0.8414 0.3137 0.3126 0.041 Uiso 1 1 calc R U . . .
C11 C 0.25491(15) 0.44891(15) -0.02620(11) 0.0212(2) Uani 1 1 d . . . . .
H11 H 0.1489 0.5458 -0.0225 0.025 Uiso 1 1 calc R U . . .
C12 C 0.36631(14) 0.39494(14) 0.05981(10) 0.0173(2) Uani 1 1 d . . . . .
C13 C 0.50824(14) 0.24475(14) 0.01865(10) 0.0174(2) Uani 1 1 d . . . . .
C14 C 0.66079(15) 0.13148(15) 0.06491(10) 0.0203(2) Uani 1 1 d . . . . .
H14 H 0.6869 0.1472 0.1400 0.024 Uiso 1 1 calc R U . . .
C15 C 0.77245(16) -0.00332(15) -0.00056(12) 0.0242(3) Uani 1 1 d . . . . .
H15 H 0.8764 -0.0802 0.0298 0.029 Uiso 1 1 calc R U . . .
C16 C 0.73443(16) -0.02829(15) -0.11135(12) 0.0259(3) Uani 1 1 d . . . . .
H16 H 0.8134 -0.1219 -0.1546 0.031 Uiso 1 1 calc R U . . .
C17 C 0.58513(16) 0.07997(16) -0.15862(11) 0.0243(3) Uani 1 1 d . . . . .
H17 H 0.5594 0.0623 -0.2332 0.029 Uiso 1 1 calc R U . . .
C18 C 0.47317(15) 0.21656(15) -0.09281(11) 0.0200(2) Uani 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 O1 H1 109.5 . . ?
C6 O3 C7 120.32(9) . . ?
C1 N1 C5 114.50(8) . . ?
C6 N1 C1 119.16(9) . . ?
C6 N1 C5 125.10(9) . . ?
C11 N2 H2 125.7 . . ?
C11 N2 C18 108.65(10) . . ?
C18 N2 H2 125.7 . . ?
N1 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
N1 C1 C2 109.85(9) . . ?
H1A C1 H1B 108.2 . . ?
C2 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
O1 C2 C1 107.95(9) . . ?
O1 C2 H2A 109.7 . . ?
O1 C2 C3 110.66(9) . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 C1 109.04(9) . . ?
C3 C2 H2A 109.7 . . ?
C2 C3 H3 118.2 . . ?
C4 C3 C2 123.58(10) . . ?
C4 C3 H3 118.2 . . ?
C3 C4 H4 118.1 . . ?
C3 C4 C5 123.84(10) . . ?
C5 C4 H4 118.1 . . ?
N1 C5 C4 108.49(9) . . ?
N1 C5 H5 108.4 . . ?
N1 C5 C12 111.61(9) . . ?
C4 C5 H5 108.4 . . ?
C12 C5 C4 111.49(9) . . ?
C12 C5 H5 108.4 . . ?
O2 C6 O3 124.17(10) . . ?
O2 C6 N1 123.57(10) . . ?
O3 C6 N1 112.24(9) . . ?
O3 C7 C8 110.04(9) . . ?
O3 C7 C9 110.35(9) . . ?
O3 C7 C10 101.60(9) . . ?
C8 C7 C9 112.51(10) . . ?
C8 C7 C10 110.91(10) . . ?
C9 C7 C10 110.92(10) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11 124.8 . . ?
C12 C11 N2 110.40(11) . . ?
C12 C11 H11 124.8 . . ?
C11 C12 C5 126.89(10) . . ?
C11 C12 C13 106.25(10) . . ?
C13 C12 C5 126.86(10) . . ?
C14 C13 C12 134.27(11) . . ?
C14 C13 C18 118.92(11) . . ?
C18 C13 C12 106.81(10) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 118.94(11) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C16 120.95(12) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.47(11) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 121.3 . . ?
C16 C17 C18 117.48(11) . . ?
C18 C17 H17 121.3 . . ?
N2 C18 C13 107.88(10) . . ?
N2 C18 C17 129.88(11) . . ?
C17 C18 C13 122.23(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
O1 H1 0.8400 . ?
O1 C2 1.4319(13) . ?
O2 C6 1.2302(14) . ?
O3 C6 1.3434(13) . ?
O3 C7 1.4820(13) . ?
N1 C1 1.4567(13) . ?
N1 C5 1.4823(14) . ?
N1 C6 1.3488(14) . ?
N2 H2 0.8800 . ?
N2 C11 1.3715(16) . ?
N2 C18 1.3750(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5203(15) . ?
C2 H2A 1.0000 . ?
C2 C3 1.5066(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3285(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.5098(15) . ?
C5 H5 1.0000 . ?
C5 C12 1.5046(15) . ?
C7 C8 1.5163(16) . ?
C7 C9 1.5230(16) . ?
C7 C10 1.5234(16) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
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 H11 0.9500 . ?
C11 C12 1.3712(16) . ?
C12 C13 1.4385(16) . ?
C13 C14 1.4040(16) . ?
C13 C18 1.4128(16) . ?
C14 H14 0.9500 . ?
C14 C15 1.3826(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.4060(19) . ?
C16 H16 0.9500 . ?
C16 C17 1.3781(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.3956(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
O1 C2 C3 C4 -135.28(11) . . . . ?
N1 C1 C2 O1 167.87(8) . . . . ?
N1 C1 C2 C3 47.59(12) . . . . ?
N1 C5 C12 C11 108.66(13) . . . . ?
N1 C5 C12 C13 -71.72(13) . . . . ?
N2 C11 C12 C5 179.30(10) . . . . ?
N2 C11 C12 C13 -0.38(13) . . . . ?
C1 N1 C5 C4 45.69(12) . . . . ?
C1 N1 C5 C12 -77.54(11) . . . . ?
C1 N1 C6 O2 2.16(16) . . . . ?
C1 N1 C6 O3 -179.21(9) . . . . ?
C1 C2 C3 C4 -16.69(15) . . . . ?
C2 C3 C4 C5 -1.05(18) . . . . ?
C3 C4 C5 N1 -11.96(15) . . . . ?
C3 C4 C5 C12 111.35(12) . . . . ?
C4 C5 C12 C11 -12.84(16) . . . . ?
C4 C5 C12 C13 166.77(11) . . . . ?
C5 N1 C1 C2 -66.41(11) . . . . ?
C5 N1 C6 O2 168.68(10) . . . . ?
C5 N1 C6 O3 -12.69(15) . . . . ?
C5 C12 C13 C14 0.6(2) . . . . ?
C5 C12 C13 C18 -179.55(10) . . . . ?
C6 O3 C7 C8 -71.60(13) . . . . ?
C6 O3 C7 C9 53.14(13) . . . . ?
C6 O3 C7 C10 170.85(10) . . . . ?
C6 N1 C1 C2 101.49(11) . . . . ?
C6 N1 C5 C4 -121.37(11) . . . . ?
C6 N1 C5 C12 115.39(11) . . . . ?
C7 O3 C6 O2 7.08(16) . . . . ?
C7 O3 C6 N1 -171.54(9) . . . . ?
C11 N2 C18 C13 -0.39(13) . . . . ?
C11 N2 C18 C17 179.70(12) . . . . ?
C11 C12 C13 C14 -179.70(12) . . . . ?
C11 C12 C13 C18 0.13(12) . . . . ?
C12 C13 C14 C15 -179.66(12) . . . . ?
C12 C13 C18 N2 0.16(13) . . . . ?
C12 C13 C18 C17 -179.93(11) . . . . ?
C13 C14 C15 C16 -0.47(18) . . . . ?
C14 C13 C18 N2 -179.98(10) . . . . ?
C14 C13 C18 C17 -0.07(17) . . . . ?
C14 C15 C16 C17 -0.07(19) . . . . ?
C15 C16 C17 C18 0.52(18) . . . . ?
C16 C17 C18 N2 179.44(12) . . . . ?
C16 C17 C18 C13 -0.45(17) . . . . ?
C18 N2 C11 C12 0.49(14) . . . . ?
C18 C13 C14 C15 0.53(16) . . . . ?
