#------------------------------------------------------------------------------
#$Date: 2021-06-26 00:36:34 +0300 (Sat, 26 Jun 2021) $
#$Revision: 266690 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/88/4518835.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_4518835
loop_
_publ_author_name
'González, Bruno'
'Fagúndez, Catherine'
'Peixoto de Abreu Lima, Alejandro'
'Suescun, Leopoldo'
'Sellanes, Diver'
'Seoane, Gustavo A.'
'Carrera, Ignacio'
_publ_section_title
;
 Efficient Access to the Iboga Skeleton: Optimized Procedure to Obtain
 Voacangine from Voacanga africana Root Bark
;
_journal_name_full               'ACS Omega'
_journal_paper_doi               10.1021/acsomega.1c00745
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'Cl, C20 H27 N2 O'
_chemical_formula_sum            'C20 H27 Cl N2 O'
_chemical_formula_weight         346.88
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-12-10 deposited with the CCDC.	2021-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3860(5)
_cell_length_b                   10.6137(8)
_cell_length_c                   18.3018(10)
_cell_measurement_reflns_used    4468
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.67
_cell_measurement_theta_min      4.82
_cell_volume                     1823.2(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEXII CCD area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25396
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.075
_diffrn_reflns_theta_min         4.816
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.910
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.5948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1073 before and 0.0778 after correction.
The Ratio of minimum to maximum transmission is 0.7899.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       irregular
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.158
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1201 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3318
_refine_ls_number_restraints     76
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0604
_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)+(0.0562P)²+1.6268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1482
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3127
_reflns_number_total             3318
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao1c00745_si_001.cif
_cod_data_source_block           19_a
_cod_database_code               4518835
_shelx_shelxl_version_number     2016/6
_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   0.752
_shelx_estimated_absorpt_t_min   0.637
_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. Restrained distances
 C18-C19
 1.53 with sigma of 0.01
3. Rigid bond restraints
 C3, C4, C5, N1, C18, C19
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N1, C5
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
C3 \\sim C4 \\sim C5 \\sim N1 \\sim C19 \\sim C18: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
C17 \\sim C18 \\sim C19 \\sim C18A \\sim C19A: within 2A with sigma of 0.005
and sigma for terminal atoms of 0.01
5. Same fragment restrains
{C17, C18A, C19A} sigma for 1-2: 0.005, 1-3: 0.04
as
{C17, C18, C19}
6. Others
 Sof(H17A)=Sof(C18A)=Sof(H18C)=Sof(H18D)=Sof(C19A)=Sof(H19D)=Sof(H19E)=
 Sof(H19F)=1-FVAR(1)
 Sof(H17)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=
 FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C15(H15), C9(H9), C10(H10), C17(H17), C17(H17A)
7.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C16(H16A,
 H16B), C18(H18A,H18B), C18A(H18C,H18D)
7.c Me refined with riding coordinates:
 C20(H20A,H20B,H20C)
7.d Aromatic/amide H refined with riding coordinates:
 C1(H1A), C3(H3), C4(H4)
7.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C19A(H19D,H19E,H19F)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
Cl1 Cl 0.99110(12) 0.69594(16) 0.62865(6) 0.0586(4) Uani 1 1 d . . . . .
O1 O 0.2251(5) 0.2142(5) 0.3358(2) 0.0716(13) Uani 1 1 d . . . . .
N2 N 0.6764(4) 0.6619(5) 0.6040(2) 0.0467(11) Uani 1 1 d . . . . .
H2 H 0.757(7) 0.665(5) 0.629(3) 0.056(16) Uiso 1 1 d . . . . .
N1 N 0.2364(5) 0.5105(5) 0.5822(3) 0.0597(12) Uani 1 1 d . U . . .
H1 H 0.165(8) 0.546(7) 0.606(4) 0.072 Uiso 1 1 d R . . . .
C7 C 0.4428(5) 0.5069(5) 0.5207(3) 0.0464(12) Uani 1 1 d . . . . .
C11 C 0.7026(5) 0.5512(6) 0.5545(3) 0.0479(13) Uani 1 1 d . . . . .
H11A H 0.708890 0.474545 0.585180 0.057 Uiso 1 1 calc R . . . .
H11B H 0.796595 0.562861 0.530909 0.057 Uiso 1 1 calc R . . . .
C6 C 0.3428(5) 0.4291(5) 0.4830(3) 0.0496(13) Uani 1 1 d . . . . .
C12 C 0.5937(5) 0.5275(6) 0.4953(3) 0.0475(12) Uani 1 1 d . . . . .
H12A H 0.594543 0.600250 0.461409 0.057 Uiso 1 1 calc R . . . .
H12B H 0.623905 0.452488 0.467077 0.057 Uiso 1 1 calc R . . . .
C8 C 0.3740(5) 0.5574(6) 0.5799(3) 0.0526(13) Uani 1 1 d . . . . .
C15 C 0.5379(5) 0.8594(6) 0.6108(3) 0.0506(13) Uani 1 1 d . . . . .
H15 H 0.526282 0.945805 0.589799 0.061 Uiso 1 1 calc R . . . .
C13 C 0.6449(5) 0.7844(6) 0.5652(3) 0.0517(13) Uani 1 1 d . . . . .
H13A H 0.604817 0.767185 0.516172 0.062 Uiso 1 1 calc R . . . .
H13B H 0.733794 0.833481 0.559067 0.062 Uiso 1 1 calc R . . . .
C5 C 0.2149(5) 0.4332(6) 0.5236(4) 0.0625(16) Uani 1 1 d . U . . .
C9 C 0.4169(5) 0.6531(6) 0.6357(3) 0.0509(13) Uani 1 1 d . . . . .
H9 H 0.351927 0.641423 0.678414 0.061 Uiso 1 1 calc R . . . .
C1 C 0.3515(6) 0.3556(5) 0.4191(3) 0.0542(14) Uani 1 1 d . . . . .
H1A H 0.437291 0.351714 0.391714 0.065 Uiso 1 1 calc R . . . .
C10 C 0.5693(5) 0.6399(6) 0.6648(3) 0.0547(15) Uani 1 1 d . . . . .
H10 H 0.582896 0.553589 0.685588 0.066 Uiso 1 1 calc R . . . .
C14 C 0.3967(5) 0.7906(6) 0.6092(3) 0.0540(13) Uani 1 1 d . . . . .
H14A H 0.358176 0.790733 0.558874 0.065 Uiso 1 1 calc R . . . .
H14B H 0.327566 0.834284 0.641293 0.065 Uiso 1 1 calc R . . . .
C2 C 0.2327(6) 0.2894(6) 0.3974(3) 0.0613(15) Uani 1 1 d . . . . .
C3 C 0.1052(6) 0.2925(7) 0.4389(5) 0.0757(19) Uani 1 1 d . U . . .
H3 H 0.025282 0.244270 0.423571 0.091 Uiso 1 1 calc R . . . .
C4 C 0.0961(7) 0.3646(7) 0.5011(4) 0.0740(18) Uani 1 1 d . U . . .
H4 H 0.010050 0.367561 0.528383 0.089 Uiso 1 1 calc R . . . .
C16 C 0.5945(6) 0.8685(7) 0.6888(3) 0.0650(17) Uani 1 1 d . . . . .
H16A H 0.534643 0.927358 0.717451 0.078 Uiso 1 1 calc R . . . .
H16B H 0.693102 0.901766 0.688216 0.078 Uiso 1 1 calc R . . . .
C20 C 0.3521(8) 0.2074(9) 0.2926(3) 0.087(2) Uani 1 1 d . . . . .
H20A H 0.335669 0.152138 0.250489 0.130 Uiso 1 1 calc R . . . .
H20B H 0.377470 0.291878 0.275371 0.130 Uiso 1 1 calc R . . . .
H20C H 0.429981 0.173409 0.322282 0.130 Uiso 1 1 calc R . . . .
C17 C 0.5927(5) 0.7384(7) 0.7246(3) 0.0597(15) Uani 1 1 d D U . . .
H17 H 0.507629 0.735481 0.757393 0.072 Uiso 0.704(10) 1 calc R . P A 1
H17A H 0.504191 0.736546 0.754936 0.072 Uiso 0.296(10) 1 calc R . P A 2
C18 C 0.7285(7) 0.7333(9) 0.7749(4) 0.0532(18) Uani 0.704(10) 1 d D U P A 1
H18A H 0.815610 0.739895 0.744686 0.064 Uiso 0.704(10) 1 calc R . P A 1
H18B H 0.727210 0.804954 0.809557 0.064 Uiso 0.704(10) 1 calc R . P A 1
C19 C 0.7291(9) 0.6102(9) 0.8167(4) 0.061(2) Uani 0.704(10) 1 d D U P A 1
H19A H 0.723317 0.539725 0.782213 0.092 Uiso 0.704(10) 1 calc GR . P A 1
H19B H 0.647159 0.607600 0.849823 0.092 Uiso 0.704(10) 1 calc GR . P A 1
H19C H 0.817347 0.603538 0.845070 0.092 Uiso 0.704(10) 1 calc GR . P A 1
C18A C 0.7079(18) 0.6644(16) 0.7703(8) 0.055(3) Uani 0.296(10) 1 d D U P A 2
H18C H 0.670560 0.583207 0.788857 0.065 Uiso 0.296(10) 1 calc R . P A 2
H18D H 0.795947 0.649368 0.741854 0.065 Uiso 0.296(10) 1 calc R . P A 2
C19A C 0.7312(18) 0.7586(19) 0.8312(8) 0.054(3) Uani 0.296(10) 1 d D U P A 2
H19D H 0.805147 0.727196 0.864343 0.081 Uiso 0.296(10) 1 calc GR . P A 2
H19E H 0.642122 0.770150 0.858398 0.081 Uiso 0.296(10) 1 calc GR . P A 2
H19F H 0.761259 0.839378 0.810428 0.081 Uiso 0.296(10) 1 calc GR . P A 2
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'
Cl Cl 0.3639 0.7018 '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 C20 115.9(5) . . ?
C11 N2 H2 102(4) . . ?
C11 N2 C13 115.0(3) . . ?
C11 N2 C10 115.4(4) . . ?
C13 N2 H2 112(4) . . ?
C13 N2 C10 110.3(4) . . ?
C10 N2 H2 101(4) . . ?
C8 N1 H1 124(5) . . ?
C5 N1 H1 123(4) . . ?
C5 N1 C8 109.3(5) . . ?
C6 C7 C12 123.5(5) . . ?
C8 C7 C6 107.4(4) . . ?
C8 C7 C12 129.1(5) . . ?
N2 C11 H11A 108.1 . . ?
N2 C11 H11B 108.1 . . ?
N2 C11 C12 116.8(4) . . ?
H11A C11 H11B 107.3 . . ?
C12 C11 H11A 108.1 . . ?
C12 C11 H11B 108.1 . . ?
C5 C6 C7 106.6(5) . . ?
C1 C6 C7 133.2(5) . . ?
C1 C6 C5 120.2(5) . . ?
C7 C12 C11 116.0(4) . . ?
C7 C12 H12A 108.3 . . ?
C7 C12 H12B 108.3 . . ?
C11 C12 H12A 108.3 . . ?
C11 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
N1 C8 C9 118.4(5) . . ?
C7 C8 N1 108.8(6) . . ?
C7 C8 C9 132.7(4) . . ?
C13 C15 H15 109.8 . . ?
C14 C15 H15 109.8 . . ?
C14 C15 C13 108.3(5) . . ?
C14 C15 C16 110.7(4) . . ?
C16 C15 H15 109.8 . . ?
C16 C15 C13 108.4(4) . . ?
N2 C13 C15 108.7(4) . . ?
N2 C13 H13A 109.9 . . ?
N2 C13 H13B 109.9 . . ?
C15 C13 H13A 109.9 . . ?
C15 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
N1 C5 C6 107.8(5) . . ?
N1 C5 C4 131.6(6) . . ?
C4 C5 C6 120.6(7) . . ?
C8 C9 H9 106.6 . . ?
C8 C9 C10 115.3(5) . . ?
C8 C9 C14 113.2(4) . . ?
C10 C9 H9 106.6 . . ?
C10 C9 C14 108.0(5) . . ?
C14 C9 H9 106.6 . . ?
C6 C1 H1A 120.8 . . ?
C2 C1 C6 118.5(5) . . ?
C2 C1 H1A 120.8 . . ?
N2 C10 C9 110.4(3) . . ?
N2 C10 H10 109.6 . . ?
N2 C10 C17 108.9(5) . . ?
C9 C10 H10 109.6 . . ?
C17 C10 C9 108.7(4) . . ?
C17 C10 H10 109.6 . . ?
C15 C14 C9 110.0(4) . . ?
C15 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
C9 C14 H14A 109.7 . . ?
C9 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
O1 C2 C3 114.0(5) . . ?
C1 C2 O1 124.9(6) . . ?
C1 C2 C3 121.1(6) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(6) . . ?
C4 C3 H3 119.7 . . ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 119.1(6) . . ?
C3 C4 H4 120.5 . . ?
C15 C16 H16A 109.7 . . ?
C15 C16 H16B 109.7 . . ?
C15 C16 C17 109.8(5) . . ?
H16A C16 H16B 108.2 . . ?
C17 C16 H16A 109.7 . . ?
C17 C16 H16B 109.7 . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 C17 H17 107.1 . . ?
C10 C17 H17A 105.3 . . ?
C10 C17 C18 120.8(5) . . ?
C10 C17 C18A 97.9(7) . . ?
C16 C17 C10 108.3(4) . . ?
C16 C17 H17 107.1 . . ?
C16 C17 H17A 105.3 . . ?
C16 C17 C18 105.8(5) . . ?
C16 C17 C18A 132.1(9) . . ?
C18 C17 H17 107.1 . . ?
C18A C17 H17A 105.3 . . ?
C17 C18 H18A 109.8 . . ?
C17 C18 H18B 109.8 . . ?
H18A C18 H18B 108.3 . . ?
C19 C18 C17 109.2(6) . . ?
C19 C18 H18A 109.8 . . ?
C19 C18 H18B 109.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C18A H18C 111.9 . . ?
C17 C18A H18D 111.9 . . ?
H18C C18A H18D 109.6 . . ?
C19A C18A C17 99.3(9) . . ?
C19A C18A H18C 111.9 . . ?
C19A C18A H18D 111.9 . . ?
C18A C19A H19D 109.5 . . ?
C18A C19A H19E 109.5 . . ?
C18A C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
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 C2 1.383(8) . ?
O1 C20 1.432(9) . ?
N2 H2 0.89(6) . ?
N2 C11 1.503(8) . ?
N2 C13 1.511(7) . ?
N2 C10 1.518(5) . ?
N1 H1 0.88(7) . ?
N1 C8 1.385(7) . ?
N1 C5 1.365(9) . ?
C7 C6 1.428(8) . ?
C7 C12 1.507(6) . ?
C7 C8 1.371(8) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.511(7) . ?
C6 C5 1.413(7) . ?
C6 C1 1.407(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C8 C9 1.495(9) . ?
C15 H15 1.0000 . ?
C15 C13 1.529(7) . ?
C15 C14 1.514(8) . ?
C15 C16 1.527(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C5 C4 1.394(10) . ?
C9 H9 1.0000 . ?
C9 C10 1.532(6) . ?
C9 C14 1.550(8) . ?
C1 H1A 0.9500 . ?
C1 C2 1.377(8) . ?
C10 H10 1.0000 . ?
C10 C17 1.529(9) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C2 C3 1.418(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.374(11) . ?
C4 H4 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.529(10) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C17 H17 1.0000 . ?
C17 H17A 1.0000 . ?
C17 C18 1.573(7) . ?
C17 C18A 1.577(9) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.514(8) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C18A H18C 0.9900 . ?
C18A H18D 0.9900 . ?
C18A C19A 1.514(10) . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
