# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
#TrackingRef '8480_web_deposit_cif_file_0_KazuteruUsui_1322820871.100827 helicene.cif'

_audit_creation_method           'APEX2 v2009.11-0'

_publ_contact_author_name        'Kazuteru Usui'
_publ_contact_author_address     
;
;
_publ_contact_author_email       usui@phar.kyushu-u.ac.jp
_publ_contact_author_fax         ?
_publ_contact_author_phone       ?

_publ_section_title              
;
;
_publ_section_abstract           
;
;
_publ_section_references         
;
;
_publ_section_comment            
;
;
loop_
_publ_author_name
T.Koghiso
Y.Kosuke
H.Suemune
K.Usui

data_I
_database_code_depnum_ccdc_archive 'CCDC 856591'
#TrackingRef '8480_web_deposit_cif_file_0_KazuteruUsui_1322820871.100827 helicene.cif'

_audit_creation_method           'APEX2 v2009.11-0'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H30 Br N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         616.53

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.9353(15)
_cell_length_b                   12.0352(17)
_cell_length_c                   12.4875(17)
_cell_angle_alpha                73.7160(10)
_cell_angle_beta                 67.7270(10)
_cell_angle_gamma                83.6170(10)
_cell_volume                     1459.8(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             636

_exptl_absorpt_coefficient_mu    1.447
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   
;
;
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            16726
_diffrn_reflns_av_R_equivalents  0.0922
_diffrn_reflns_av_sigmaI/netI    0.0707
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         28.51
_diffrn_reflns_theta_full        28.51
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measured_fraction_theta_full 0.913
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             6761
_reflns_number_gt                6298
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_gt          0.1526
_refine_ls_wR_factor_ref         0.1542
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_number_reflns         6761
_refine_ls_number_parameters     382
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0826P)^2^+1.5551P] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         1.419
_refine_diff_density_min         -1.125
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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
Br Br1 0.26660(2) 0.44807(2) 0.36950(2) 0.02526(11) Uani d . 1 . .
O O1 0.37714(18) 0.58049(16) -0.18649(16) 0.0220(4) Uani d . 1 . .
O O2 0.09913(18) 0.79267(13) 0.05840(17) 0.0217(4) Uani d . 1 . .
O O3 0.6327(4) 0.7746(2) 0.3688(2) 0.0675(9) Uani d . 1 . .
N N1 0.2454(2) 0.68574(17) -0.05940(18) 0.0149(4) Uani d . 1 . .
C C1 0.0256(2) 0.3522(2) 0.5548(2) 0.0209(5) Uani d . 1 . .
H H1 0.0362 0.4029 0.5947 0.025 Uiso calc R 1 . .
C C2 0.1143(2) 0.3526(2) 0.4386(2) 0.0178(5) Uani d . 1 . .
C C3 0.0963(2) 0.2855(2) 0.3739(2) 0.0151(4) Uani d . 1 . .
H H3 0.1573 0.2878 0.2973 0.018 Uiso calc R 1 . .
C C4 -0.0150(2) 0.2125(2) 0.4233(2) 0.0145(4) Uani d . 1 . .
C C5 -0.0435(2) 0.1434(2) 0.3567(2) 0.0138(4) Uani d . 1 . .
C C6 0.0175(2) 0.1632(2) 0.2279(2) 0.0145(4) Uani d . 1 . .
C C7 0.0695(2) 0.2727(2) 0.1450(2) 0.0140(4) Uani d . 1 . .
C C8 0.0205(2) 0.3843(2) 0.1663(2) 0.0128(4) Uani d . 1 . .
C C9 0.0943(2) 0.4850(2) 0.0902(2) 0.0127(4) Uani d . 1 . .
C C10 0.2083(2) 0.4771(2) -0.0126(2) 0.0141(4) Uani d . 1 . .
C C11 0.2843(2) 0.5823(2) -0.0936(2) 0.0154(4) Uani d . 1 . .
C C12 0.3193(2) 0.7925(2) -0.1362(2) 0.0185(5) Uani d . 1 . .
H H12A 0.2581 0.8573 -0.1316 0.022 Uiso calc R 1 . .
H H12B 0.3541 0.7871 -0.2185 0.022 Uiso calc R 1 . .
C C13 0.4352(2) 0.8187(2) -0.1047(2) 0.0240(5) Uani d . 1 . .
C C14 0.5513(2) 0.7372(2) -0.1422(4) 0.0398(8) Uani d . 1 . .
H H14A 0.5716 0.7371 -0.224 0.06 Uiso calc R 1 . .
H H14B 0.5284 0.6603 -0.0917 0.06 Uiso calc R 1 . .
H H14C 0.6269 0.7628 -0.1345 0.06 Uiso calc R 1 . .
C C15 -0.1257(2) 0.0468(2) 0.4227(2) 0.0176(5) Uani d . 1 . .
C C16 -0.2009(2) 0.0325(2) 0.5486(2) 0.0211(5) Uani d . 1 . .
H H16 -0.2564 -0.0309 0.5912 0.025 Uiso calc R 1 . .
C C17 -0.1921(2) 0.1098(2) 0.6058(2) 0.0212(5) Uani d . 1 . .
H H17 -0.2484 0.1039 0.6847 0.025 Uiso calc R 1 . .
C C18 -0.0968(2) 0.2005(2) 0.5457(2) 0.0177(5) Uani d . 1 . .
C C19 -0.0771(2) 0.2747(2) 0.6078(2) 0.0213(5) Uani d . 1 . .
H H19 -0.1347 0.271 0.6858 0.026 Uiso calc R 1 . .
C C20 -0.1309(2) -0.0392(2) 0.3661(2) 0.0207(5) Uani d . 1 . .
H H20 -0.1898 -0.1003 0.4085 0.025 Uiso calc R 1 . .
C C21 -0.0502(2) -0.0326(2) 0.2503(2) 0.0206(5) Uani d . 1 . .
H H21 -0.0461 -0.094 0.2175 0.025 Uiso calc R 1 . .
C C22 0.0276(2) 0.0679(2) 0.1793(2) 0.0172(5) Uani d . 1 . .
C C23 0.1179(2) 0.0725(2) 0.0599(2) 0.0198(5) Uani d . 1 . .
H H23 0.1247 0.01 0.028 0.024 Uiso calc R 1 . .
C C24 0.1939(2) 0.1676(2) -0.0069(2) 0.0189(5) Uani d . 1 . .
H H24 0.2625 0.1652 -0.0786 0.023 Uiso calc R 1 . .
C C25 0.1686(2) 0.2711(2) 0.0324(2) 0.0152(4) Uani d . 1 . .
C C26 0.2397(2) 0.3741(2) -0.0426(2) 0.0165(4) Uani d . 1 . .
H H26 0.309 0.3711 -0.1137 0.02 Uiso calc R 1 . .
C C27 0.3942(2) 0.8118(2) 0.0291(2) 0.0340(7) Uani d . 1 . .
H H27A 0.3662 0.7345 0.0755 0.051 Uiso calc R 1 . .
H H27B 0.3228 0.8649 0.0516 0.051 Uiso calc R 1 . .
H H27C 0.4681 0.8315 0.0437 0.051 Uiso calc R 1 . .
C C28 0.4775(2) 0.9434(2) -0.1773(2) 0.0402(8) Uani d . 1 . .
H H28A 0.5553 0.9617 -0.1677 0.06 Uiso calc R 1 . .
H H28B 0.4075 0.9959 -0.1491 0.06 Uiso calc R 1 . .
H H28C 0.4961 0.9505 -0.2605 0.06 Uiso calc R 1 . .
C C29 0.1308(2) 0.6987(2) 0.0381(2) 0.0153(4) Uani d . 1 . .
C C30 0.0511(2) 0.5939(2) 0.1126(2) 0.0131(4) Uani d . 1 . .
C C31 -0.1031(2) 0.3999(2) 0.2544(2) 0.0151(4) Uani d . 1 . .
H H31 -0.1565 0.3359 0.3014 0.018 Uiso calc R 1 . .
C C32 -0.1464(2) 0.5077(2) 0.2722(2) 0.0160(4) Uani d . 1 . .
H H32 -0.2282 0.5156 0.3305 0.019 Uiso calc R 1 . .
C C33 -0.0676(2) 0.6052(2) 0.2028(2) 0.0151(4) Uani d . 1 . .
H H33 -0.095 0.6773 0.2172 0.018 Uiso calc R 1 . .
C C34 0.5058(5) 0.7752(5) 0.4741(4) 0.0667(16) Uani d . 1 . .
H H34A 0.5227 0.7641 0.5473 0.08 Uiso calc R 1 . .
H H34B 0.4573 0.847 0.4607 0.08 Uiso calc R 1 . .
C C35 0.4326(4) 0.6742(5) 0.4789(4) 0.0694(17) Uani d . 1 . .
H H35A 0.3378 0.6859 0.5121 0.083 Uiso calc R 1 . .
H H35B 0.4561 0.6027 0.5266 0.083 Uiso calc R 1 . .
C C36 0.4780(2) 0.6724(2) 0.3483(4) 0.0461(9) Uani d . 1 . .
H H36A 0.4859 0.5935 0.3413 0.055 Uiso calc R 1 . .
H H36B 0.4158 0.7139 0.3126 0.055 Uiso calc R 1 . .
C C37 0.6017(2) 0.7272(2) 0.2922(2) 0.0274(5) Uani d . 1 . .
H H37A 0.6693 0.6713 0.265 0.033 Uiso calc R 1 . .
H H37B 0.6013 0.7881 0.2224 0.033 Uiso calc R 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.02174(17) 0.02345(16) 0.03419(17) -0.00827(11) -0.01012(12) -0.00996(12)
O1 0.0182(9) 0.0234(9) 0.0182(8) -0.0082(7) 0.0034(7) -0.0067(7)
O2 0.0179(9) 0.0134(7) 0.0276(9) -0.0044(5) -0.0005(7) -0.0051(7)
O3 0.064(2) 0.075(2) 0.075(2) -0.0063(17) -0.0290(18) -0.0290(18)
N1 0.0122(9) 0.0132(8) 0.0156(9) -0.0060(7) -0.0016(7) -0.0008(7)
C1 0.0256(13) 0.0194(11) 0.0205(11) -0.0010(10) -0.0096(10) -0.0073(9)
C2 0.0173(11) 0.0165(10) 0.0220(11) -0.0030(9) -0.0097(9) -0.0042(9)
C3 0.0131(10) 0.0156(10) 0.0160(10) -0.0025(8) -0.0048(8) -0.0031(8)
C4 0.0123(10) 0.0131(9) 0.0164(10) -0.0033(8) -0.0051(9) 0.0000(8)
C5 0.0111(10) 0.0130(9) 0.0158(10) -0.0022(8) -0.0038(8) -0.0021(8)
C6 0.0127(10) 0.0136(10) 0.0166(10) -0.0035(8) -0.0047(9) -0.0026(8)
C7 0.0140(10) 0.0134(10) 0.0146(10) -0.0037(8) -0.0044(8) -0.0032(8)
C8 0.0113(10) 0.0130(9) 0.0132(9) -0.0030(8) -0.0036(8) -0.0022(8)
C9 0.0112(10) 0.0141(10) 0.0127(9) -0.0030(8) -0.0039(8) -0.0029(8)
C10 0.0122(10) 0.0157(10) 0.0132(9) -0.0044(8) -0.0029(8) -0.0027(8)
C11 0.0127(10) 0.0178(10) 0.0147(10) -0.0042(8) -0.0032(8) -0.0034(8)
C12 0.0144(11) 0.0157(10) 0.0190(11) -0.0076(9) -0.0016(9) 0.0017(9)
C13 0.0139(11) 0.0232(11) 0.0330(14) -0.0084(9) -0.0028(10) -0.0094(11)
C14 0.0188(14) 0.0473(18) 0.066(2) 0.0043(13) -0.0179(15) -0.0323(17)
C15 0.0139(11) 0.0162(10) 0.0204(11) -0.0034(8) -0.0057(9) -0.0007(9)
C16 0.0150(11) 0.0182(11) 0.0212(11) -0.0057(9) -0.0016(9) 0.0034(9)
C17 0.0161(11) 0.0203(11) 0.0190(11) -0.0028(9) -0.0015(9) 0.0012(9)
C18 0.0164(11) 0.0168(10) 0.0164(10) -0.0014(9) -0.0044(9) -0.0006(9)
C19 0.0241(13) 0.0220(11) 0.0153(10) 0.0012(10) -0.0047(9) -0.0052(9)
C20 0.0190(11) 0.0129(10) 0.0283(11) -0.0071(9) -0.0093(10) 0.0010(9)
C21 0.0248(13) 0.0128(10) 0.0273(11) -0.0048(9) -0.0131(11) -0.0034(9)
C22 0.0179(11) 0.0148(10) 0.0210(11) -0.0020(9) -0.0091(9) -0.0042(9)
C23 0.0236(11) 0.0157(10) 0.0220(11) 0.0000(9) -0.0087(10) -0.0074(9)
C24 0.0210(11) 0.0173(11) 0.0183(11) 0.0008(9) -0.0052(9) -0.0076(9)
C25 0.0156(11) 0.0145(10) 0.0147(10) -0.0022(8) -0.0038(9) -0.0040(8)
C26 0.0161(11) 0.0172(10) 0.0142(10) -0.0036(9) -0.0027(9) -0.0035(8)
C27 0.0267(15) 0.0433(17) 0.0374(16) -0.0114(13) -0.0122(13) -0.0139(14)
C28 0.0317(17) 0.0309(15) 0.048(2) -0.0217(13) 0.0005(14) -0.0079(14)
C29 0.0114(10) 0.0141(10) 0.0177(10) -0.0053(8) -0.0022(9) -0.0025(8)
C30 0.0120(10) 0.0132(10) 0.0133(9) -0.0048(8) -0.0034(8) -0.0023(8)
C31 0.0124(10) 0.0152(10) 0.0141(9) -0.0055(8) -0.0024(8) 0.0001(8)
C32 0.0128(10) 0.0178(10) 0.0140(10) -0.0041(8) -0.0019(8) -0.0017(8)
C33 0.0140(11) 0.0132(9) 0.0161(10) -0.0025(8) -0.0024(9) -0.0045(8)
C34 0.072(3) 0.096(4) 0.0352(18) 0.057(3) -0.025(2) -0.035(2)
C35 0.0267(18) 0.080(3) 0.049(2) 0.002(2) 0.0072(17) 0.032(2)
C36 0.0195(15) 0.0371(17) 0.075(3) -0.0121(13) -0.0095(16) -0.0096(17)
C37 0.0209(13) 0.0394(15) 0.0173(11) -0.0248(11) 0.0106(10) -0.0157(11)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Br1 C2 . 1.902(2) ?
O1 C11 . 1.222(3) ?
O2 C29 . 1.213(3) ?
O3 C37 . 1.396(4) ?
O3 C34 . 1.508(6) ?
N1 C11 . 1.398(3) ?
N1 C29 . 1.408(3) ?
N1 C12 . 1.475(3) ?
C1 C19 . 1.376(4) ?
C1 C2 . 1.405(4) ?
C1 H1 . 0.93 ?
C2 C3 . 1.367(3) ?
C3 C4 . 1.414(3) ?
C3 H3 . 0.93 ?
C4 C18 . 1.423(3) ?
C4 C5 . 1.457(3) ?
C5 C15 . 1.404(3) ?
C5 C6 . 1.448(3) ?
C6 C22 . 1.415(3) ?
C6 C7 . 1.445(3) ?
C7 C25 . 1.416(3) ?
C7 C8 . 1.447(3) ?
C8 C31 . 1.416(3) ?
C8 C9 . 1.419(3) ?
C9 C30 . 1.409(3) ?
C9 C10 . 1.428(3) ?
C10 C26 . 1.365(3) ?
C10 C11 . 1.482(3) ?
C12 C13 . 1.548(4) ?
C12 H12A . 0.97 ?
C12 H12B . 0.97 ?
C13 C14 . 1.525(4) ?
C13 C28 . 1.537(4) ?
C13 C27 . 1.537(4) ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C15 C20 . 1.423(4) ?
C15 C16 . 1.441(3) ?
C16 C17 . 1.353(4) ?
C16 H16 . 0.93 ?
C17 C18 . 1.429(3) ?
C17 H17 . 0.93 ?
C18 C19 . 1.415(4) ?
C19 H19 . 0.93 ?
C20 C21 . 1.364(4) ?
C20 H20 . 0.93 ?
C21 C22 . 1.425(3) ?
C21 H21 . 0.93 ?
C22 C23 . 1.432(3) ?
C23 C24 . 1.359(3) ?
C23 H23 . 0.93 ?
C24 C25 . 1.426(3) ?
C24 H24 . 0.93 ?
C25 C26 . 1.425(3) ?
C26 H26 . 0.93 ?
C27 H27A . 0.96 ?
C27 H27B . 0.96 ?
C27 H27C . 0.96 ?
C28 H28A . 0.96 ?
C28 H28B . 0.96 ?
C28 H28C . 0.96 ?
C29 C30 . 1.479(3) ?
C30 C33 . 1.382(3) ?
C31 C32 . 1.379(3) ?
C31 H31 . 0.93 ?
C32 C33 . 1.401(3) ?
C32 H32 . 0.93 ?
C33 H33 . 0.93 ?
C34 C35 . 1.504(8) ?
C34 H34A . 0.97 ?
C34 H34B . 0.97 ?
C35 C36 . 1.520(7) ?
C35 H35A . 0.97 ?
C35 H35B . 0.97 ?
C36 C37 . 1.406(4) ?
C36 H36A . 0.97 ?
C36 H36B . 0.97 ?
C37 H37A . 0.97 ?
C37 H37B . 0.97 ?

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
C37 O3 C34 . . 106.1(3) ?
C11 N1 C29 . . 124.3(2) ?
C11 N1 C12 . . 119.1(2) ?
C29 N1 C12 . . 116.3(2) ?
C19 C1 C2 . . 118.2(2) ?
C19 C1 H1 . . 120.9 ?
C2 C1 H1 . . 120.9 ?
C3 C2 C1 . . 122.4(2) ?
C3 C2 Br1 . . 118.6(2) ?
C1 C2 Br1 . . 119.0(2) ?
C2 C3 C4 . . 119.9(2) ?
C2 C3 H3 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C3 C4 C18 . . 118.2(2) ?
C3 C4 C5 . . 122.6(2) ?
C18 C4 C5 . . 119.0(2) ?
C15 C5 C6 . . 118.7(2) ?
C15 C5 C4 . . 117.6(2) ?
C6 C5 C4 . . 123.4(2) ?
C22 C6 C7 . . 117.4(2) ?
C22 C6 C5 . . 117.6(2) ?
C7 C6 C5 . . 124.9(2) ?
C25 C7 C6 . . 118.0(2) ?
C25 C7 C8 . . 117.7(2) ?
C6 C7 C8 . . 124.1(2) ?
C31 C8 C9 . . 117.5(2) ?
C31 C8 C7 . . 123.3(2) ?
C9 C8 C7 . . 119.1(2) ?
C30 C9 C8 . . 119.9(2) ?
C30 C9 C10 . . 119.9(2) ?
C8 C9 C10 . . 120.1(2) ?
C26 C10 C9 . . 119.6(2) ?
C26 C10 C11 . . 119.7(2) ?
C9 C10 C11 . . 120.3(2) ?
O1 C11 N1 . . 120.5(2) ?
O1 C11 C10 . . 122.4(2) ?
N1 C11 C10 . . 117.1(2) ?
N1 C12 C13 . . 115.4(2) ?
N1 C12 H12A . . 108.4 ?
C13 C12 H12A . . 108.4 ?
N1 C12 H12B . . 108.4 ?
C13 C12 H12B . . 108.4 ?
H12A C12 H12B . . 107.5 ?
C14 C13 C28 . . 109.1(3) ?
C14 C13 C27 . . 109.9(3) ?
C28 C13 C27 . . 108.7(3) ?
C14 C13 C12 . . 110.7(2) ?
C28 C13 C12 . . 105.9(2) ?
C27 C13 C12 . . 112.5(2) ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C5 C15 C20 . . 119.9(2) ?
C5 C15 C16 . . 120.0(2) ?
C20 C15 C16 . . 120.0(2) ?
C17 C16 C15 . . 121.1(2) ?
C17 C16 H16 . . 119.4 ?
C15 C16 H16 . . 119.4 ?
C16 C17 C18 . . 120.3(2) ?
C16 C17 H17 . . 119.8 ?
C18 C17 H17 . . 119.8 ?
C19 C18 C4 . . 119.3(2) ?
C19 C18 C17 . . 121.0(2) ?
C4 C18 C17 . . 119.7(2) ?
C1 C19 C18 . . 121.2(2) ?
C1 C19 H19 . . 119.4 ?
C18 C19 H19 . . 119.4 ?
C21 C20 C15 . . 120.6(2) ?
C21 C20 H20 . . 119.7 ?
C15 C20 H20 . . 119.7 ?
C20 C21 C22 . . 120.3(2) ?
C20 C21 H21 . . 119.8 ?
C22 C21 H21 . . 119.8 ?
C6 C22 C21 . . 119.8(2) ?
C6 C22 C23 . . 119.7(2) ?
C21 C22 C23 . . 120.5(2) ?
C24 C23 C22 . . 120.4(2) ?
C24 C23 H23 . . 119.8 ?
C22 C23 H23 . . 119.8 ?
C23 C24 C25 . . 120.1(2) ?
C23 C24 H24 . . 119.9 ?
C25 C24 H24 . . 119.9 ?
C7 C25 C26 . . 119.8(2) ?
C7 C25 C24 . . 119.9(2) ?
C26 C25 C24 . . 120.3(2) ?
C10 C26 C25 . . 121.4(2) ?
C10 C26 H26 . . 119.3 ?
C25 C26 H26 . . 119.3 ?
C13 C27 H27A . . 109.5 ?
C13 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C13 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C13 C28 H28A . . 109.5 ?
C13 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C13 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
O2 C29 N1 . . 120.7(2) ?
O2 C29 C30 . . 122.0(2) ?
N1 C29 C30 . . 117.3(2) ?
C33 C30 C9 . . 120.8(2) ?
C33 C30 C29 . . 118.7(2) ?
C9 C30 C29 . . 120.5(2) ?
C32 C31 C8 . . 121.6(2) ?
C32 C31 H31 . . 119.2 ?
C8 C31 H31 . . 119.2 ?
C31 C32 C33 . . 120.1(2) ?
C31 C32 H32 . . 119.9 ?
C33 C32 H32 . . 119.9 ?
C30 C33 C32 . . 119.7(2) ?
C30 C33 H33 . . 120.1 ?
C32 C33 H33 . . 120.1 ?
C35 C34 O3 . . 102.4(3) ?
C35 C34 H34A . . 111.3 ?
O3 C34 H34A . . 111.3 ?
C35 C34 H34B . . 111.3 ?
O3 C34 H34B . . 111.3 ?
H34A C34 H34B . . 109.2 ?
C34 C35 C36 . . 103.4(3) ?
C34 C35 H35A . . 111.1 ?
C36 C35 H35A . . 111.1 ?
C34 C35 H35B . . 111.1 ?
C36 C35 H35B . . 111.1 ?
H35A C35 H35B . . 109.1 ?
C37 C36 C35 . . 105.4(3) ?
C37 C36 H36A . . 110.7 ?
C35 C36 H36A . . 110.7 ?
C37 C36 H36B . . 110.7 ?
C35 C36 H36B . . 110.7 ?
H36A C36 H36B . . 108.8 ?
O3 C37 C36 . . 112.1(3) ?
O3 C37 H37A . . 109.2 ?
C36 C37 H37A . . 109.2 ?
O3 C37 H37B . . 109.2 ?
C36 C37 H37B . . 109.2 ?
H37A C37 H37B . . 107.9 ?