#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/78/2227871.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_2227871
loop_
_publ_author_name
'Karpoormath, Rajshekhar'
'Govender, Thavendran'
'Govender, Patrick'
'Kruger, Hendrik G.'
'Maguire, Glenn E. M.'
_publ_section_title
;
 tert-Butyl
 N-[(11-exo-benzyloxycarbonyl-8-oxopentacyclo[5.4.0.0^2,6^.0^3,10^.0^5,9^]undecane-11-endo-yloxy)carbonylmethyl]carbamate
;
_journal_coeditor_code           OM2360
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2607
_journal_page_last               o2608
_journal_paper_doi               10.1107/S1600536810036627
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C26 H29 N O7'
_chemical_formula_moiety         'C26 H29 N O7'
_chemical_formula_sum            'C26 H29 N O7'
_chemical_formula_weight         467.50
_chemical_name_systematic
;
tert-Butyl N-[(11-exo-benzyloxycarbonyl-8-
oxopentacyclo[5.4.0.0^2,6^.0^3,10^.0^5,9^]undecane-11-endo-
yloxy)carbonylmethyl]carbamate
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.6790(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7260(2)
_cell_length_b                   27.5398(7)
_cell_length_c                   9.3500(2)
_cell_measurement_reflns_used    8919
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.13
_cell_measurement_theta_min      5.92
_cell_volume                     2386.14(9)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker Kappa DUO APEXII'
_diffrn_measurement_method       '0.5° φ scans and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8919
_diffrn_reflns_theta_full        68.13
_diffrn_reflns_theta_max         68.13
_diffrn_reflns_theta_min         5.92
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.178
_refine_ls_abs_structure_details 'Flack (1983), 1760 Friedel pairs'
_refine_ls_abs_structure_Flack   0.00(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         3948
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0509P)²+1.0452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.0999
_reflns_number_gt                3802
_reflns_number_total             3948
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            om2360.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2227871
_cod_database_fobs_code          2227871
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.65693(19) 1.00052(6) 0.9771(2) 0.0521(4) Uani d . 1 . .
O O2 0.76432(15) 0.90113(5) 0.91549(15) 0.0358(3) Uani d . 1 . .
O O3 0.7061(2) 0.87716(7) 0.67501(18) 0.0564(5) Uani d . 1 . .
O O4 1.1178(2) 0.90102(8) 0.6733(2) 0.0619(5) Uani d . 1 . .
O O5 1.00520(16) 0.93227(6) 0.44177(16) 0.0452(4) Uani d . 1 . .
O O6 0.5895(2) 0.78765(6) 0.8670(3) 0.0661(5) Uani d . 1 . .
O O7 0.8234(2) 0.80702(6) 0.9488(3) 0.0642(5) Uani d . 1 . .
N N1 0.9078(2) 0.94186(8) 0.6227(2) 0.0454(4) Uani d D 1 . .
H H1N 0.836(2) 0.9596(8) 0.549(2) 0.049(7) Uiso d D 1 . .
C C1 0.4838(3) 0.88257(10) 1.2375(3) 0.0584(6) Uani d . 1 . .
H H1A 0.5564 0.8807 1.3379 0.070 Uiso calc R 1 . .
H H1B 0.3871 0.8739 1.2442 0.070 Uiso calc R 1 . .
C C2 0.4852(3) 0.93103(9) 1.1615(3) 0.0504(6) Uani d . 1 . .
H H2 0.4599 0.9597 1.2140 0.060 Uiso calc R 1 . .
C C3 0.6376(3) 0.93282(8) 1.1385(2) 0.0423(5) Uani d . 1 . .
H H3 0.7140 0.9474 1.2248 0.051 Uiso calc R 1 . .
C C4 0.6031(2) 0.96254(8) 0.9971(2) 0.0411(5) Uani d . 1 . .
C C5 0.4713(3) 0.93899(8) 0.8917(3) 0.0464(5) Uani d . 1 . .
H H5 0.4163 0.9584 0.8021 0.056 Uiso calc R 1 . .
C C6 0.3875(3) 0.92269(9) 1.0015(3) 0.0507(6) Uani d . 1 . .
H H6 0.2846 0.9332 0.9777 0.061 Uiso calc R 1 . .
C C7 0.5258(3) 0.85303(8) 1.1207(3) 0.0503(6) Uani d . 1 . .
H H7 0.5335 0.8173 1.1397 0.060 Uiso calc R 1 . .
C C8 0.6645(2) 0.87760(8) 1.1087(2) 0.0385(4) Uani d . 1 . .
H H8 0.7545 0.8642 1.1809 0.046 Uiso calc R 1 . .
C C9 0.6564(2) 0.86978(7) 0.9442(2) 0.0375(4) Uani d . 1 . .
C C10 0.5005(3) 0.88424(8) 0.8639(3) 0.0445(5) Uani d . 1 . .
H H10 0.4605 0.8727 0.7579 0.053 Uiso calc R 1 . .
C C11 0.4164(3) 0.86818(9) 0.9720(3) 0.0503(6) Uani d . 1 . .
H H11 0.3305 0.8468 0.9305 0.060 Uiso calc R 1 . .
C C12 0.7770(2) 0.90133(7) 0.7760(2) 0.0377(4) Uani d . 1 . .
C C13 0.8940(3) 0.93654(8) 0.7718(2) 0.0422(5) Uani d . 1 . .
H H13A 0.8725 0.9686 0.8077 0.051 Uiso calc R 1 . .
H H13B 0.9870 0.9252 0.8409 0.051 Uiso calc R 1 . .
C C14 1.0199(2) 0.92285(8) 0.5870(2) 0.0394(5) Uani d . 1 . .
C C15 1.1196(2) 0.91702(8) 0.3776(2) 0.0402(5) Uani d . 1 . .
C C16 1.2606(3) 0.94073(13) 0.4606(3) 0.0650(8) Uani d . 1 . .
H H16A 1.2484 0.9761 0.4575 0.097 Uiso calc R 1 . .
H H16B 1.3340 0.9318 0.4131 0.097 Uiso calc R 1 . .
H H16C 1.2911 0.9297 0.5652 0.097 Uiso calc R 1 . .
C C17 1.0661(3) 0.93591(14) 0.2193(3) 0.0681(8) Uani d . 1 . .
H H17A 1.0606 0.9714 0.2210 0.102 Uiso calc R 1 . .
H H17B 0.9701 0.9225 0.1694 0.102 Uiso calc R 1 . .
H H17C 1.1328 0.9260 0.1644 0.102 Uiso calc R 1 . .
C C18 1.1285(4) 0.86241(11) 0.3777(4) 0.0756(9) Uani d . 1 . .
H H18A 1.0340 0.8489 0.3228 0.113 Uiso calc R 1 . .
H H18B 1.1574 0.8505 0.4814 0.113 Uiso calc R 1 . .
H H18C 1.2000 0.8523 0.3290 0.113 Uiso calc R 1 . .
C C19 0.6842(3) 0.81669(8) 0.9137(3) 0.0483(5) Uani d . 1 . .
C C20 0.8571(4) 0.75648(10) 0.9237(6) 0.1008(15) Uani d . 1 . .
H H20A 0.7839 0.7436 0.8334 0.121 Uiso calc R 1 . .
H H20B 0.8553 0.7364 1.0109 0.121 Uiso calc R 1 . .
C C21 1.0032(3) 0.75425(8) 0.9029(3) 0.0489(6) Uani d . 1 . .
C C22 1.0989(4) 0.71945(11) 0.9751(3) 0.0657(8) Uani d . 1 . .
H H22 1.0766 0.6993 1.0474 0.079 Uiso calc R 1 . .
C C23 1.2270(3) 0.71335(13) 0.9445(4) 0.0726(8) Uani d . 1 . .
H H23 1.2910 0.6882 0.9931 0.087 Uiso calc R 1 . .
C C24 1.2633(3) 0.74254(11) 0.8465(5) 0.0752(9) Uani d . 1 . .
H H24 1.3543 0.7389 0.8298 0.090 Uiso calc R 1 . .
C C25 1.1698(4) 0.77737(10) 0.7713(3) 0.0625(7) Uani d . 1 . .
H H25 1.1948 0.7976 0.7008 0.075 Uiso calc R 1 . .
C C26 1.0372(3) 0.78318(9) 0.7980(3) 0.0537(6) Uani d . 1 . .
H H26 0.9707 0.8069 0.7442 0.064 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 O2 C9 . . 117.85(16) ?
C14 O5 C15 . . 119.49(17) ?
C19 O7 C20 . . 114.5(2) ?
C14 N1 C13 . . 121.39(19) ?
C14 N1 H1N . . 119.6(17) ?
C13 N1 H1N . . 119.0(17) ?
C7 C1 C2 . . 95.3(2) ?
C7 C1 H1A . . 112.7 ?
C2 C1 H1A . . 112.7 ?
C7 C1 H1B . . 112.7 ?
C2 C1 H1B . . 112.7 ?
H1A C1 H1B . . 110.2 ?
C1 C2 C6 . . 103.6(2) ?
C1 C2 C3 . . 103.7(2) ?
C6 C2 C3 . . 101.79(18) ?
C1 C2 H2 . . 115.3 ?
C6 C2 H2 . . 115.3 ?
C3 C2 H2 . . 115.3 ?
C4 C3 C2 . . 99.81(19) ?
C4 C3 C8 . . 111.90(17) ?
C2 C3 C8 . . 102.04(17) ?
C4 C3 H3 . . 113.9 ?
C2 C3 H3 . . 113.9 ?
C8 C3 H3 . . 113.9 ?
O1 C4 C3 . . 128.0(2) ?
O1 C4 C5 . . 126.4(2) ?
C3 C4 C5 . . 105.04(19) ?
C4 C5 C6 . . 101.77(19) ?
C4 C5 C10 . . 111.17(19) ?
C6 C5 C10 . . 89.40(18) ?
C4 C5 H5 . . 116.8 ?
C6 C5 H5 . . 116.8 ?
C10 C5 H5 . . 116.8 ?
C2 C6 C5 . . 107.93(19) ?
C2 C6 C11 . . 103.0(2) ?
C5 C6 C11 . . 90.14(18) ?
C2 C6 H6 . . 117.3 ?
C5 C6 H6 . . 117.3 ?
C11 C6 H6 . . 117.3 ?
C1 C7 C11 . . 104.1(2) ?
C1 C7 C8 . . 104.5(2) ?
C11 C7 C8 . . 101.31(18) ?
C1 C7 H7 . . 115.1 ?
C11 C7 H7 . . 115.1 ?
C8 C7 H7 . . 115.1 ?
C9 C8 C7 . . 103.44(18) ?
C9 C8 C3 . . 110.57(17) ?
C7 C8 C3 . . 102.31(17) ?
C9 C8 H8 . . 113.2 ?
C7 C8 H8 . . 113.2 ?
C3 C8 H8 . . 113.2 ?
O2 C9 C10 . . 114.94(17) ?
O2 C9 C19 . . 110.94(17) ?
C10 C9 C19 . . 111.30(18) ?
O2 C9 C8 . . 106.48(16) ?
C10 C9 C8 . . 101.39(17) ?
C19 C9 C8 . . 111.31(18) ?
C9 C10 C11 . . 104.35(19) ?
C9 C10 C5 . . 111.82(18) ?
C11 C10 C5 . . 90.48(18) ?
C9 C10 H10 . . 115.7 ?
C11 C10 H10 . . 115.7 ?
C5 C10 H10 . . 115.7 ?
C7 C11 C10 . . 108.19(19) ?
C7 C11 C6 . . 102.3(2) ?
C10 C11 C6 . . 89.98(18) ?
C7 C11 H11 . . 117.4 ?
C10 C11 H11 . . 117.4 ?
C6 C11 H11 . . 117.4 ?
O3 C12 O2 . . 124.4(2) ?
O3 C12 C13 . . 126.89(19) ?
O2 C12 C13 . . 108.69(17) ?
N1 C13 C12 . . 112.50(19) ?
N1 C13 H13A . . 109.1 ?
C12 C13 H13A . . 109.1 ?
N1 C13 H13B . . 109.1 ?
C12 C13 H13B . . 109.1 ?
H13A C13 H13B . . 107.8 ?
O4 C14 N1 . . 124.4(2) ?
O4 C14 O5 . . 126.3(2) ?
N1 C14 O5 . . 109.31(19) ?
O5 C15 C16 . . 110.40(19) ?
O5 C15 C17 . . 102.88(18) ?
C16 C15 C17 . . 110.2(2) ?
O5 C15 C18 . . 109.52(19) ?
C16 C15 C18 . . 113.0(2) ?
C17 C15 C18 . . 110.4(2) ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C15 C17 H17A . . 109.5 ?
C15 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C15 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C15 C18 H18A . . 109.5 ?
C15 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C15 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
O6 C19 O7 . . 125.0(2) ?
O6 C19 C9 . . 123.1(2) ?
O7 C19 C9 . . 111.9(2) ?
O7 C20 C21 . . 109.1(2) ?
O7 C20 H20A . . 109.9 ?
C21 C20 H20A . . 109.9 ?
O7 C20 H20B . . 109.9 ?
C21 C20 H20B . . 109.9 ?
H20A C20 H20B . . 108.3 ?
C22 C21 C26 . . 118.9(3) ?
C22 C21 C20 . . 119.8(3) ?
C26 C21 C20 . . 120.8(3) ?
C21 C22 C23 . . 120.6(3) ?
C21 C22 H22 . . 119.7 ?
C23 C22 H22 . . 119.7 ?
C24 C23 C22 . . 120.8(3) ?
C24 C23 H23 . . 119.6 ?
C22 C23 H23 . . 119.6 ?
C23 C24 C25 . . 120.1(3) ?
C23 C24 H24 . . 119.9 ?
C25 C24 H24 . . 119.9 ?
C24 C25 C26 . . 119.8(3) ?
C24 C25 H25 . . 120.1 ?
C26 C25 H25 . . 120.1 ?
C21 C26 C25 . . 119.7(2) ?
C21 C26 H26 . . 120.2 ?
C25 C26 H26 . . 120.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 . 1.210(3) ?
O2 C12 . 1.347(2) ?
O2 C9 . 1.445(2) ?
O3 C12 . 1.189(3) ?
O4 C14 . 1.205(3) ?
O5 C14 . 1.347(3) ?
O5 C15 . 1.476(2) ?
O6 C19 . 1.198(3) ?
O7 C19 . 1.320(3) ?
O7 C20 . 1.465(3) ?
N1 C14 . 1.340(3) ?
N1 C13 . 1.448(3) ?
N1 H1N . 0.955(10) ?
C1 C7 . 1.514(4) ?
C1 C2 . 1.514(4) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 C6 . 1.526(4) ?
C2 C3 . 1.562(3) ?
C2 H2 . 1.0000 ?
C3 C4 . 1.504(3) ?
C3 C8 . 1.582(3) ?
C3 H3 . 1.0000 ?
C4 C5 . 1.506(3) ?
C5 C6 . 1.559(4) ?
C5 C10 . 1.570(3) ?
C5 H5 . 1.0000 ?
C6 C11 . 1.567(3) ?
C6 H6 . 1.0000 ?
C7 C11 . 1.530(4) ?
C7 C8 . 1.544(3) ?
C7 H7 . 1.0000 ?
C8 C9 . 1.531(3) ?
C8 H8 . 1.0000 ?
C9 C10 . 1.527(3) ?
C9 C19 . 1.529(3) ?
C10 C11 . 1.546(3) ?
C10 H10 . 1.0000 ?
C11 H11 . 1.0000 ?
C12 C13 . 1.505(3) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C15 C16 . 1.504(4) ?
C15 C17 . 1.505(3) ?
C15 C18 . 1.506(4) ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C20 C21 . 1.494(4) ?
C20 H20A . 0.9900 ?
C20 H20B . 0.9900 ?
C21 C22 . 1.364(4) ?
C21 C26 . 1.379(3) ?
C22 C23 . 1.371(5) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.343(5) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.361(5) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.395(4) ?
C25 H25 . 0.9500 ?
C26 H26 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1N O1 2_574 0.955(10) 1.993(15) 2.882(2) 154(2)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 C1 C2 C6 . . . . 52.8(2) ?
C7 C1 C2 C3 . . . . -53.2(2) ?
C1 C2 C3 C4 . . . . 149.0(2) ?
C6 C2 C3 C4 . . . . 41.6(2) ?
C1 C2 C3 C8 . . . . 33.9(2) ?
C6 C2 C3 C8 . . . . -73.4(2) ?
C2 C3 C4 O1 . . . . 122.5(3) ?
C8 C3 C4 O1 . . . . -130.2(2) ?
C2 C3 C4 C5 . . . . -49.2(2) ?
C8 C3 C4 C5 . . . . 58.2(2) ?
O1 C4 C5 C6 . . . . -136.1(2) ?
C3 C4 C5 C6 . . . . 35.7(2) ?
O1 C4 C5 C10 . . . . 129.9(3) ?
C3 C4 C5 C10 . . . . -58.2(2) ?
C1 C2 C6 C5 . . . . -128.2(2) ?
C3 C2 C6 C5 . . . . -20.8(2) ?
C1 C2 C6 C11 . . . . -33.8(2) ?
C3 C2 C6 C11 . . . . 73.7(2) ?
C4 C5 C6 C2 . . . . -8.2(2) ?
C10 C5 C6 C2 . . . . 103.3(2) ?
C4 C5 C6 C11 . . . . -111.89(19) ?
C10 C5 C6 C11 . . . . -0.38(18) ?
C2 C1 C7 C11 . . . . -52.6(2) ?
C2 C1 C7 C8 . . . . 53.3(2) ?
C1 C7 C8 C9 . . . . -148.1(2) ?
C11 C7 C8 C9 . . . . -40.1(2) ?
C1 C7 C8 C3 . . . . -33.1(2) ?
C11 C7 C8 C3 . . . . 74.8(2) ?
C4 C3 C8 C9 . . . . 3.2(2) ?
C2 C3 C8 C9 . . . . 109.08(19) ?
C4 C3 C8 C7 . . . . -106.4(2) ?
C2 C3 C8 C7 . . . . -0.6(2) ?
C12 O2 C9 C10 . . . . -67.7(2) ?
C12 O2 C9 C19 . . . . 59.7(2) ?
C12 O2 C9 C8 . . . . -179.06(17) ?
C7 C8 C9 O2 . . . . 167.11(17) ?
C3 C8 C9 O2 . . . . 58.2(2) ?
C7 C8 C9 C10 . . . . 46.57(19) ?
C3 C8 C9 C10 . . . . -62.3(2) ?
C7 C8 C9 C19 . . . . -71.9(2) ?
C3 C8 C9 C19 . . . . 179.23(18) ?
O2 C9 C10 C11 . . . . -148.11(17) ?
C19 C9 C10 C11 . . . . 84.7(2) ?
C8 C9 C10 C11 . . . . -33.7(2) ?
O2 C9 C10 C5 . . . . -51.7(3) ?
C19 C9 C10 C5 . . . . -178.88(19) ?
C8 C9 C10 C5 . . . . 62.7(2) ?
C4 C5 C10 C9 . . . . -2.9(3) ?
C6 C5 C10 C9 . . . . -105.3(2) ?
C4 C5 C10 C11 . . . . 102.8(2) ?
C6 C5 C10 C11 . . . . 0.38(19) ?
C1 C7 C11 C10 . . . . 127.0(2) ?
C8 C7 C11 C10 . . . . 18.7(2) ?
C1 C7 C11 C6 . . . . 32.9(2) ?
C8 C7 C11 C6 . . . . -75.4(2) ?
C9 C10 C11 C7 . . . . 9.3(2) ?
C5 C10 C11 C7 . . . . -103.4(2) ?
C9 C10 C11 C6 . . . . 112.32(18) ?
C5 C10 C11 C6 . . . . -0.38(18) ?
C2 C6 C11 C7 . . . . 0.6(2) ?
C5 C6 C11 C7 . . . . 109.02(19) ?
C2 C6 C11 C10 . . . . -108.1(2) ?
C5 C6 C11 C10 . . . . 0.38(19) ?
C9 O2 C12 O3 . . . . -0.6(3) ?
C9 O2 C12 C13 . . . . 179.57(17) ?
C14 N1 C13 C12 . . . . -107.3(3) ?
O3 C12 C13 N1 . . . . 4.5(3) ?
O2 C12 C13 N1 . . . . -175.63(18) ?
C13 N1 C14 O4 . . . . -1.3(4) ?
C13 N1 C14 O5 . . . . 178.9(2) ?
C15 O5 C14 O4 . . . . -2.7(4) ?
C15 O5 C14 N1 . . . . 176.98(19) ?
C14 O5 C15 C16 . . . . -59.9(3) ?
C14 O5 C15 C17 . . . . -177.5(2) ?
C14 O5 C15 C18 . . . . 65.1(3) ?
C20 O7 C19 O6 . . . . 1.1(4) ?
C20 O7 C19 C9 . . . . 179.3(3) ?
O2 C9 C19 O6 . . . . -147.2(2) ?
C10 C9 C19 O6 . . . . -17.9(3) ?
C8 C9 C19 O6 . . . . 94.5(3) ?
O2 C9 C19 O7 . . . . 34.5(3) ?
C10 C9 C19 O7 . . . . 163.9(2) ?
C8 C9 C19 O7 . . . . -83.8(2) ?
C19 O7 C20 C21 . . . . 155.9(3) ?
O7 C20 C21 C22 . . . . 134.8(3) ?
O7 C20 C21 C26 . . . . -52.9(5) ?
C26 C21 C22 C23 . . . . 0.2(5) ?
C20 C21 C22 C23 . . . . 172.6(3) ?
C21 C22 C23 C24 . . . . 2.3(5) ?
C22 C23 C24 C25 . . . . -2.9(5) ?
C23 C24 C25 C26 . . . . 1.1(5) ?
C22 C21 C26 C25 . . . . -2.0(4) ?
C20 C21 C26 C25 . . . . -174.3(3) ?
C24 C25 C26 C21 . . . . 1.4(4) ?
