#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:56:18 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178412 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/33/4023309.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_4023309
loop_
_publ_author_name
'Benjamin W. Gung'
'Francis Wekesa'
'Charles L. Barnes'
_publ_section_title
;
 Stacking Interactions between Nitrogen-Containing Six-Membered
 Heterocyclic Aromatic Rings and Substituted Benzene: Studies in Solution
 and in the Solid State
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1803
_journal_page_last               1808
_journal_paper_doi               10.1021/jo702354x
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C37 H29 Br N2 O4'
_chemical_formula_weight         645.53
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.476(2)
_cell_angle_beta                 102.547(2)
_cell_angle_gamma                108.457(2)
_cell_formula_units_Z            2
_cell_length_a                   9.7052(9)
_cell_length_b                   11.7214(11)
_cell_length_c                   14.5203(14)
_cell_measurement_temperature    173(2)
_cell_volume                     1472.3(2)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10638
_diffrn_reflns_theta_full        27.21
_diffrn_reflns_theta_max         27.21
_diffrn_reflns_theta_min         1.49
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    1.442
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.50
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Data were corrected for decay and absorption using the program SADABS 
 (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of
 Göttingen, Germany).
;
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         6369
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0419
_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)+(0.0491P)²+0.6322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1045
_reflns_number_gt                4979
_reflns_number_total             6369
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702354x-File002.cif
_cod_data_source_block           RG426
_cod_database_code               4023309
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.06964(3) 0.31961(2) 0.04410(2) 0.04065(10) Uani 1 1 d . . .
O1 O 0.67839(19) 1.00439(16) 0.49379(12) 0.0300(4) Uani 1 1 d . . .
O2 O 0.9319(2) 1.06834(19) 0.56181(16) 0.0470(5) Uani 1 1 d . . .
O3 O 0.71556(19) 1.42395(15) 0.35614(12) 0.0299(4) Uani 1 1 d . . .
O4 O 0.8967(2) 1.4077(2) 0.28764(18) 0.0533(6) Uani 1 1 d . . .
N1 N 0.7220(3) 0.6319(2) 0.58481(18) 0.0453(6) Uani 1 1 d . . .
N2 N 0.6315(3) 0.7835(2) 0.53232(16) 0.0355(5) Uani 1 1 d . . .
C1 C 0.6915(3) 1.1096(2) 0.45756(17) 0.0259(5) Uani 1 1 d . . .
C2 C 0.7695(3) 1.2284(2) 0.52130(18) 0.0298(5) Uani 1 1 d . . .
H2 H 0.8155 1.2376 0.5884 0.036 Uiso 1 1 calc R . .
C3 C 0.7808(3) 1.3338(2) 0.48814(18) 0.0304(5) Uani 1 1 d . . .
H3 H 0.8338 1.4151 0.5318 0.037 Uiso 1 1 calc R . .
C4 C 0.7137(3) 1.3178(2) 0.39070(18) 0.0267(5) Uani 1 1 d . . .
C5 C 0.6794(3) 1.1127(3) 0.09091(19) 0.0338(6) Uani 1 1 d . . .
H5 H 0.6905 1.1874 0.0714 0.041 Uiso 1 1 calc R . .
C6 C 0.7308(3) 1.0268(3) 0.0474(2) 0.0371(6) Uani 1 1 d . . .
H6 H 0.7766 1.0417 -0.0030 0.044 Uiso 1 1 calc R . .
C7 C 0.7164(3) 0.9185(3) 0.0764(2) 0.0380(6) Uani 1 1 d . . .
H7 H 0.7515 0.8594 0.0453 0.046 Uiso 1 1 calc R . .
C8 C 0.6509(3) 0.8953(3) 0.15102(18) 0.0314(6) Uani 1 1 d . . .
H8 H 0.6444 0.8222 0.1723 0.038 Uiso 1 1 calc R . .
C9 C 0.5175(3) 0.9698(2) 0.27618(17) 0.0233(5) Uani 1 1 d . . .
C10 C 0.5513(3) 1.1754(2) 0.21977(18) 0.0270(5) Uani 1 1 d . . .
H10 H 0.5643 1.2535 0.1982 0.032 Uiso 1 1 calc R . .
C11 C 0.2667(3) 1.1373(2) 0.17940(18) 0.0294(5) Uani 1 1 d . . .
H11 H 0.2822 1.2132 0.1611 0.035 Uiso 1 1 calc R . .
C12 C 0.1218(3) 1.0603(3) 0.17544(19) 0.0346(6) Uani 1 1 d . . .
H12 H 0.0371 1.0828 0.1531 0.042 Uiso 1 1 calc R . .
C13 C 0.1005(3) 0.9514(2) 0.20387(19) 0.0313(6) Uani 1 1 d . . .
H13 H 0.0012 0.8994 0.2008 0.038 Uiso 1 1 calc R . .
C14 C 0.2232(3) 0.9171(2) 0.23695(17) 0.0266(5) Uani 1 1 d . . .
H14 H 0.2078 0.8424 0.2571 0.032 Uiso 1 1 calc R . .
C15 C 0.6345(3) 1.2008(2) 0.32706(18) 0.0252(5) Uani 1 1 d . . .
C16 C 0.6196(2) 1.0925(2) 0.35957(17) 0.0234(5) Uani 1 1 d . . .
C17 C 0.6110(3) 1.0891(2) 0.16396(17) 0.0272(5) Uani 1 1 d . . .
C18 C 0.5950(2) 0.9804(2) 0.19390(17) 0.0246(5) Uani 1 1 d . . .
C19 C 0.3875(3) 1.1014(2) 0.21045(17) 0.0255(5) Uani 1 1 d . . .
C20 C 0.3681(2) 0.9921(2) 0.24046(16) 0.0236(5) Uani 1 1 d . . .
C21 C 0.8066(3) 0.9903(2) 0.53914(19) 0.0317(6) Uani 1 1 d . . .
C22 C 0.7760(3) 0.8635(2) 0.55728(18) 0.0300(5) Uani 1 1 d . . .
C23 C 0.8964(3) 0.8327(3) 0.5968(2) 0.0398(6) Uani 1 1 d . . .
H23 H 0.9978 0.8913 0.6152 0.048 Uiso 1 1 calc R . .
C24 C 0.8664(4) 0.7141(3) 0.6092(2) 0.0437(7) Uani 1 1 d . . .
H24 H 0.9482 0.6900 0.6351 0.052 Uiso 1 1 calc R . .
C25 C 0.6122(3) 0.6721(3) 0.5479(2) 0.0361(6) Uani 1 1 d . . .
H25 H 0.5104 0.6149 0.5312 0.043 Uiso 1 1 calc R . .
C26 C 0.8093(3) 1.4570(2) 0.29991(18) 0.0286(5) Uani 1 1 d . . .
C27 C 0.7834(3) 1.5576(2) 0.25384(19) 0.0316(6) Uani 1 1 d . . .
C28 C 0.7810(4) 1.6637(3) 0.3318(2) 0.0438(7) Uani 1 1 d . . .
H28A H 0.6934 1.6324 0.3560 0.066 Uiso 1 1 calc R . .
H28B H 0.7733 1.7316 0.3030 0.066 Uiso 1 1 calc R . .
H28C H 0.8749 1.6949 0.3863 0.066 Uiso 1 1 calc R . .
C29 C 0.9114(3) 1.6060(3) 0.2090(2) 0.0428(7) Uani 1 1 d . . .
H29A H 1.0085 1.6458 0.2609 0.064 Uiso 1 1 calc R . .
H29B H 0.8929 1.6672 0.1751 0.064 Uiso 1 1 calc R . .
H29C H 0.9149 1.5361 0.1621 0.064 Uiso 1 1 calc R . .
C30 C 0.6302(3) 1.4992(3) 0.1730(2) 0.0444(7) Uani 1 1 d . . .
H30A H 0.6316 1.4303 0.1241 0.067 Uiso 1 1 calc R . .
H30B H 0.6129 1.5627 0.1415 0.067 Uiso 1 1 calc R . .
H30C H 0.5483 1.4674 0.2019 0.067 Uiso 1 1 calc R . .
C31 C 0.4959(3) 0.8498(2) 0.30855(17) 0.0248(5) Uani 1 1 d . . .
H31A H 0.5976 0.8450 0.3296 0.030 Uiso 1 1 calc R . .
H31B H 0.4605 0.8597 0.3674 0.030 Uiso 1 1 calc R . .
C32 C 0.3893(3) 0.7238(2) 0.23795(17) 0.0252(5) Uani 1 1 d . . .
C33 C 0.3255(3) 0.7004(2) 0.13793(18) 0.0295(5) Uani 1 1 d . . .
H33 H 0.3465 0.7674 0.1083 0.035 Uiso 1 1 calc R . .
C34 C 0.2312(3) 0.5809(2) 0.08023(18) 0.0304(5) Uani 1 1 d . . .
H34 H 0.1890 0.5663 0.0118 0.037 Uiso 1 1 calc R . .
C35 C 0.1994(3) 0.4835(2) 0.12313(18) 0.0283(5) Uani 1 1 d . . .
C36 C 0.2581(3) 0.5035(2) 0.22279(19) 0.0305(5) Uani 1 1 d . . .
H36 H 0.2342 0.4366 0.2523 0.037 Uiso 1 1 calc R . .
C37 C 0.3524(3) 0.6230(2) 0.27854(18) 0.0281(5) Uani 1 1 d . . .
H37 H 0.3936 0.6371 0.3471 0.034 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C21 O1 C1 118.62(19) . . ?
C26 O3 C4 116.72(18) . . ?
C25 N1 C24 116.3(2) . . ?
C25 N2 C22 115.8(2) . . ?
C16 C1 C2 121.2(2) . . ?
C16 C1 O1 119.2(2) . . ?
C2 C1 O1 119.5(2) . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 118.4(2) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C15 121.4(2) . . ?
C3 C4 O3 119.5(2) . . ?
C15 C4 O3 118.9(2) . . ?
C6 C5 C17 119.3(3) . . ?
C6 C5 H5 120.3 . . ?
C17 C5 H5 120.3 . . ?
C5 C6 C7 120.5(2) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C8 120.7(3) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C18 C8 C7 119.2(3) . . ?
C18 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C31 C9 C18 114.96(19) . . ?
C31 C9 C20 114.05(18) . . ?
C18 C9 C20 106.14(18) . . ?
C31 C9 C16 114.21(18) . . ?
C18 C9 C16 103.33(18) . . ?
C20 C9 C16 102.84(18) . . ?
C17 C10 C19 107.79(19) . . ?
C17 C10 C15 105.57(19) . . ?
C19 C10 C15 104.28(18) . . ?
C17 C10 H10 112.9 . . ?
C19 C10 H10 112.9 . . ?
C15 C10 H10 112.9 . . ?
C19 C11 C12 118.7(2) . . ?
C19 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.6(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C20 C14 C13 119.8(2) . . ?
C20 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C4 C15 C16 121.0(2) . . ?
C4 C15 C10 124.6(2) . . ?
C16 C15 C10 114.3(2) . . ?
C1 C16 C15 117.1(2) . . ?
C1 C16 C9 130.6(2) . . ?
C15 C16 C9 112.34(19) . . ?
C5 C17 C18 121.0(2) . . ?
C5 C17 C10 125.5(2) . . ?
C18 C17 C10 113.5(2) . . ?
C8 C18 C17 119.3(2) . . ?
C8 C18 C9 126.5(2) . . ?
C17 C18 C9 114.2(2) . . ?
C11 C19 C20 121.7(2) . . ?
C11 C19 C10 125.0(2) . . ?
C20 C19 C10 113.3(2) . . ?
C14 C20 C19 118.8(2) . . ?
C14 C20 C9 127.0(2) . . ?
C19 C20 C9 114.17(19) . . ?
O2 C21 O1 124.7(2) . . ?
O2 C21 C22 122.9(2) . . ?
O1 C21 C22 112.5(2) . . ?
N2 C22 C23 122.2(2) . . ?
N2 C22 C21 118.7(2) . . ?
C23 C22 C21 119.0(2) . . ?
C22 C23 C24 118.2(3) . . ?
C22 C23 H23 120.9 . . ?
C24 C23 H23 120.9 . . ?
N1 C24 C23 120.7(3) . . ?
N1 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
N2 C25 N1 126.7(3) . . ?
N2 C25 H25 116.6 . . ?
N1 C25 H25 116.6 . . ?
O4 C26 O3 122.2(2) . . ?
O4 C26 C27 125.7(2) . . ?
O3 C26 C27 112.0(2) . . ?
C26 C27 C29 108.3(2) . . ?
C26 C27 C28 109.8(2) . . ?
C29 C27 C28 110.6(2) . . ?
C26 C27 C30 108.5(2) . . ?
C29 C27 C30 109.6(2) . . ?
C28 C27 C30 109.9(2) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 C9 120.32(19) . . ?
C32 C31 H31A 107.2 . . ?
C9 C31 H31A 107.2 . . ?
C32 C31 H31B 107.2 . . ?
C9 C31 H31B 107.2 . . ?
H31A C31 H31B 106.9 . . ?
C33 C32 C37 117.3(2) . . ?
C33 C32 C31 126.2(2) . . ?
C37 C32 C31 116.5(2) . . ?
C32 C33 C34 121.2(2) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
C35 C34 C33 119.5(2) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C34 C35 C36 121.0(2) . . ?
C34 C35 Br1 119.54(19) . . ?
C36 C35 Br1 119.47(18) . . ?
C35 C36 C37 118.4(2) . . ?
C35 C36 H36 120.8 . . ?
C37 C36 H36 120.8 . . ?
C36 C37 C32 122.5(2) . . ?
C36 C37 H37 118.8 . . ?
C32 C37 H37 118.8 . . ?
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
Br1 C35 1.906(2) . ?
O1 C21 1.350(3) . ?
O1 C1 1.407(3) . ?
O2 C21 1.199(3) . ?
O3 C26 1.363(3) . ?
O3 C4 1.420(3) . ?
O4 C26 1.193(3) . ?
N1 C25 1.343(4) . ?
N1 C24 1.350(4) . ?
N2 C25 1.327(3) . ?
N2 C22 1.342(3) . ?
C1 C16 1.388(3) . ?
C1 C2 1.389(3) . ?
C2 C3 1.386(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(3) . ?
C3 H3 0.9500 . ?
C4 C15 1.375(3) . ?
C5 C6 1.373(4) . ?
C5 C17 1.393(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(4) . ?
C7 H7 0.9500 . ?
C8 C18 1.393(3) . ?
C8 H8 0.9500 . ?
C9 C31 1.529(3) . ?
C9 C18 1.547(3) . ?
C9 C20 1.550(3) . ?
C9 C16 1.568(3) . ?
C10 C17 1.513(3) . ?
C10 C19 1.513(3) . ?
C10 C15 1.517(3) . ?
C10 H10 1.0000 . ?
C11 C19 1.381(3) . ?
C11 C12 1.393(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(3) . ?
C13 H13 0.9500 . ?
C14 C20 1.387(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.409(3) . ?
C17 C18 1.394(3) . ?
C19 C20 1.397(3) . ?
C21 C22 1.504(3) . ?
C22 C23 1.370(4) . ?
C23 C24 1.381(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C27 1.517(3) . ?
C27 C29 1.526(4) . ?
C27 C28 1.532(4) . ?
C27 C30 1.537(4) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.525(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.388(3) . ?
C32 C37 1.396(3) . ?
C33 C34 1.389(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.380(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.381(3) . ?
C36 C37 1.382(3) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
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
C21 O1 C1 C16 125.1(2) . . . . ?
C21 O1 C1 C2 -58.1(3) . . . . ?
C16 C1 C2 C3 -1.6(4) . . . . ?
O1 C1 C2 C3 -178.3(2) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C15 1.1(4) . . . . ?
C2 C3 C4 O3 176.1(2) . . . . ?
C26 O3 C4 C3 107.8(3) . . . . ?
C26 O3 C4 C15 -77.1(3) . . . . ?
C17 C5 C6 C7 -0.7(4) . . . . ?
C5 C6 C7 C8 -0.6(4) . . . . ?
C6 C7 C8 C18 2.2(4) . . . . ?
C19 C11 C12 C13 1.2(4) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C12 C13 C14 C20 -0.7(4) . . . . ?
C3 C4 C15 C16 -0.2(4) . . . . ?
O3 C4 C15 C16 -175.21(19) . . . . ?
C3 C4 C15 C10 177.1(2) . . . . ?
O3 C4 C15 C10 2.1(3) . . . . ?
C17 C10 C15 C4 126.8(2) . . . . ?
C19 C10 C15 C4 -119.7(2) . . . . ?
C17 C10 C15 C16 -55.7(2) . . . . ?
C19 C10 C15 C16 57.7(2) . . . . ?
C2 C1 C16 C15 2.5(3) . . . . ?
O1 C1 C16 C15 179.2(2) . . . . ?
C2 C1 C16 C9 -175.6(2) . . . . ?
O1 C1 C16 C9 1.1(4) . . . . ?
C4 C15 C16 C1 -1.6(3) . . . . ?
C10 C15 C16 C1 -179.1(2) . . . . ?
C4 C15 C16 C9 176.8(2) . . . . ?
C10 C15 C16 C9 -0.7(3) . . . . ?
C31 C9 C16 C1 -0.9(3) . . . . ?
C18 C9 C16 C1 -126.5(2) . . . . ?
C20 C9 C16 C1 123.2(3) . . . . ?
C31 C9 C16 C15 -179.02(19) . . . . ?
C18 C9 C16 C15 55.4(2) . . . . ?
C20 C9 C16 C15 -54.9(2) . . . . ?
C6 C5 C17 C18 0.5(4) . . . . ?
C6 C5 C17 C10 178.9(2) . . . . ?
C19 C10 C17 C5 126.2(2) . . . . ?
C15 C10 C17 C5 -122.8(2) . . . . ?
C19 C10 C17 C18 -55.3(3) . . . . ?
C15 C10 C17 C18 55.7(2) . . . . ?
C7 C8 C18 C17 -2.4(3) . . . . ?
C7 C8 C18 C9 179.3(2) . . . . ?
C5 C17 C18 C8 1.1(3) . . . . ?
C10 C17 C18 C8 -177.5(2) . . . . ?
C5 C17 C18 C9 179.6(2) . . . . ?
C10 C17 C18 C9 1.0(3) . . . . ?
C31 C9 C18 C8 -2.8(3) . . . . ?
C20 C9 C18 C8 -129.9(2) . . . . ?
C16 C9 C18 C8 122.3(2) . . . . ?
C31 C9 C18 C17 178.76(19) . . . . ?
C20 C9 C18 C17 51.7(2) . . . . ?
C16 C9 C18 C17 -56.1(2) . . . . ?
C12 C11 C19 C20 -1.9(4) . . . . ?
C12 C11 C19 C10 -179.3(2) . . . . ?
C17 C10 C19 C11 -127.6(2) . . . . ?
C15 C10 C19 C11 120.5(3) . . . . ?
C17 C10 C19 C20 54.8(3) . . . . ?
C15 C10 C19 C20 -57.1(3) . . . . ?
C13 C14 C20 C19 0.0(3) . . . . ?
C13 C14 C20 C9 179.2(2) . . . . ?
C11 C19 C20 C14 1.3(4) . . . . ?
C10 C19 C20 C14 179.0(2) . . . . ?
C11 C19 C20 C9 -178.0(2) . . . . ?
C10 C19 C20 C9 -0.3(3) . . . . ?
C31 C9 C20 C14 1.1(3) . . . . ?
C18 C9 C20 C14 128.7(2) . . . . ?
C16 C9 C20 C14 -123.1(2) . . . . ?
C31 C9 C20 C19 -179.7(2) . . . . ?
C18 C9 C20 C19 -52.1(3) . . . . ?
C16 C9 C20 C19 56.0(2) . . . . ?
C1 O1 C21 O2 9.5(4) . . . . ?
C1 O1 C21 C22 -169.5(2) . . . . ?
C25 N2 C22 C23 -0.3(4) . . . . ?
C25 N2 C22 C21 178.4(2) . . . . ?
O2 C21 C22 N2 177.8(3) . . . . ?
O1 C21 C22 N2 -3.1(3) . . . . ?
O2 C21 C22 C23 -3.5(4) . . . . ?
O1 C21 C22 C23 175.6(2) . . . . ?
N2 C22 C23 C24 1.3(4) . . . . ?
C21 C22 C23 C24 -177.4(2) . . . . ?
C25 N1 C24 C23 0.5(4) . . . . ?
C22 C23 C24 N1 -1.4(4) . . . . ?
C22 N2 C25 N1 -0.7(4) . . . . ?
C24 N1 C25 N2 0.6(4) . . . . ?
C4 O3 C26 O4 -7.1(4) . . . . ?
C4 O3 C26 C27 170.8(2) . . . . ?
O4 C26 C27 C29 -12.9(4) . . . . ?
O3 C26 C27 C29 169.4(2) . . . . ?
O4 C26 C27 C28 -133.8(3) . . . . ?
O3 C26 C27 C28 48.5(3) . . . . ?
O4 C26 C27 C30 106.1(3) . . . . ?
O3 C26 C27 C30 -71.6(3) . . . . ?
C18 C9 C31 C32 -65.7(3) . . . . ?
C20 C9 C31 C32 57.2(3) . . . . ?
C16 C9 C31 C32 175.06(19) . . . . ?
C9 C31 C32 C33 12.1(4) . . . . ?
C9 C31 C32 C37 -167.5(2) . . . . ?
C37 C32 C33 C34 -1.4(4) . . . . ?
C31 C32 C33 C34 179.0(2) . . . . ?
C32 C33 C34 C35 0.5(4) . . . . ?
C33 C34 C35 C36 0.9(4) . . . . ?
C33 C34 C35 Br1 179.79(19) . . . . ?
C34 C35 C36 C37 -1.4(4) . . . . ?
Br1 C35 C36 C37 179.76(18) . . . . ?
C35 C36 C37 C32 0.4(4) . . . . ?
C33 C32 C37 C36 1.0(4) . . . . ?
C31 C32 C37 C36 -179.4(2) . . . . ?
