data_d20430
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C34 H30 O4' _chemical_formula_sum             'C34 H30 O4' _chemical_formula_weight          502.58
 
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'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            triclinic
_symmetry_space_group_name_H-M    'P -1'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    10.044(3)
_cell_length_b                    12.223(3)
_cell_length_c                    12.450(3)
_cell_angle_alpha                 81.343(7)
_cell_angle_beta                  71.583(7)
_cell_angle_gamma                 66.010(7)
_cell_volume                      1324.6(6)
_cell_formula_units_Z             2
_cell_measurement_temperature     238(2)
_cell_measurement_reflns_used     9965
_cell_measurement_theta_min       2.315
_cell_measurement_theta_max       24.841
 
_exptl_crystal_description        prism
_exptl_crystal_colour             colorless
_exptl_crystal_size_max           0.32
_exptl_crystal_size_mid           0.26
_exptl_crystal_size_min           0.07
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.260
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              532
_exptl_absorpt_coefficient_mu     0.081
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9744
_exptl_absorpt_correction_T_max   0.9943
_exptl_absorpt_process_details    'SADABS'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       238(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'D8 Venture'
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             43775
_diffrn_reflns_av_R_equivalents   0.0684
_diffrn_reflns_av_sigmaI/netI     0.0345
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          2.31
_diffrn_reflns_theta_max          25.25
_reflns_number_total              4710
_reflns_number_gt                 3718
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement   'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material   'WinGX publication routines (Farrugia, 2005)'
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0372P)²+0.5931P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.020(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          4710
_refine_ls_number_parameters      347
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0625
_refine_ls_R_factor_gt            0.0447
_refine_ls_wR_factor_ref          0.1065
_refine_ls_wR_factor_gt           0.0961
_refine_ls_goodness_of_fit_ref    1.040
_refine_ls_restrained_S_all       1.040
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
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
C1 C 0.73460(19) 0.47596(15) 0.65873(15) 0.0309(4) Uani 1 1 d . . .
H1 H 0.8119 0.4609 0.5841 0.037 Uiso 1 1 calc R . .
C2 C 0.66394(19) 0.61039(14) 0.68416(14) 0.0270(4) Uani 1 1 d . . .
H2 H 0.6968 0.6208 0.7477 0.032 Uiso 1 1 calc R . .
C3 C 0.71025(18) 0.68992(14) 0.58539(14) 0.0256(4) Uani 1 1 d . . .
C4 C 0.8537(2) 0.69338(16) 0.55908(15) 0.0338(4) Uani 1 1 d . . .
H4 H 0.9212 0.6447 0.6007 0.041 Uiso 1 1 calc R . .
C5 C 0.8984(2) 0.76748(17) 0.47252(16) 0.0386(5) Uani 1 1 d . . .
H5 H 0.9956 0.7692 0.4559 0.046 Uiso 1 1 calc R . .
C6 C 0.8002(2) 0.83889(17) 0.41059(16) 0.0434(5) Uani 1 1 d . . .
H6 H 0.8296 0.8904 0.3527 0.052 Uiso 1 1 calc R . .
C7 C 0.6590(2) 0.83427(19) 0.43402(17) 0.0483(5) Uani 1 1 d . . .
H7 H 0.5926 0.8818 0.3911 0.058 Uiso 1 1 calc R . .
C8 C 0.6145(2) 0.75992(17) 0.52057(15) 0.0370(4) Uani 1 1 d . . .
H8 H 0.5182 0.7569 0.5355 0.044 Uiso 1 1 calc R . .
C9 C 0.49470(19) 0.63804(14) 0.72681(14) 0.0266(4) Uani 1 1 d . . .
C10 C 0.39191(19) 0.75268(15) 0.77132(14) 0.0281(4) Uani 1 1 d . . .
C11 C 0.3100(2) 0.85108(15) 0.80674(14) 0.0298(4) Uani 1 1 d . . .
C12 C 0.20737(19) 0.96984(15) 0.84262(14) 0.0288(4) Uani 1 1 d . . .
C13 C 0.2609(2) 1.05037(17) 0.86484(17) 0.0393(5) Uani 1 1 d . . .
H13 H 0.3640 1.0253 0.8612 0.047 Uiso 1 1 calc R . .
C14 C 0.1636(2) 1.16645(18) 0.89212(18) 0.0482(5) Uani 1 1 d . . .
H14 H 0.2008 1.2205 0.9062 0.058 Uiso 1 1 calc R . .
C15 C 0.0119(2) 1.20407(17) 0.89894(17) 0.0448(5) Uani 1 1 d . . .
H15 H -0.0537 1.2838 0.9166 0.054 Uiso 1 1 calc R . .
C16 C -0.0434(2) 1.12508(18) 0.87991(16) 0.0416(5) Uani 1 1 d . . .
H16 H -0.1473 1.1505 0.8862 0.050 Uiso 1 1 calc R . .
C17 C 0.0533(2) 1.00813(16) 0.85154(15) 0.0345(4) Uani 1 1 d . . .
H17 H 0.0149 0.9545 0.8383 0.041 Uiso 1 1 calc R . .
C18 C 0.45939(19) 0.54646(14) 0.71440(13) 0.0259(4) Uani 1 1 d . . .
C19 C 0.30779(19) 0.54133(14) 0.74516(14) 0.0277(4) Uani 1 1 d . . .
C20 C 0.1911(2) 0.60281(17) 0.83713(16) 0.0366(4) Uani 1 1 d . . .
H20 H 0.2075 0.6517 0.8790 0.044 Uiso 1 1 calc R . .
C21 C 0.0513(2) 0.59273(18) 0.86753(17) 0.0426(5) Uani 1 1 d . . .
H21 H -0.0261 0.6346 0.9299 0.051 Uiso 1 1 calc R . .
C22 C 0.0249(2) 0.52174(17) 0.80712(17) 0.0411(5) Uani 1 1 d . . .
H22 H -0.0699 0.5149 0.8283 0.049 Uiso 1 1 calc R . .
C23 C 0.1384(2) 0.46094(17) 0.71558(17) 0.0396(5) Uani 1 1 d . . .
H23 H 0.1206 0.4130 0.6737 0.048 Uiso 1 1 calc R . .
C24 C 0.2786(2) 0.47010(16) 0.68502(16) 0.0337(4) Uani 1 1 d . . .
H24 H 0.3554 0.4276 0.6227 0.040 Uiso 1 1 calc R . .
C25 C 0.60161(19) 0.44227(14) 0.65760(14) 0.0266(4) Uani 1 1 d . . .
H25 H 0.6034 0.4436 0.5775 0.032 Uiso 1 1 calc R . .
C26 C 0.61478(18) 0.31824(14) 0.70610(14) 0.0264(4) Uani 1 1 d . . .
C27 C 0.56079(19) 0.29460(15) 0.82257(15) 0.0292(4) Uani 1 1 d . . .
C28 C 0.4188(3) 0.3803(2) 1.00510(16) 0.0527(6) Uani 1 1 d . . .
H28A H 0.3361 0.3573 1.0076 0.079 Uiso 1 1 calc R . .
H28B H 0.3780 0.4567 1.0412 0.079 Uiso 1 1 calc R . .
H28C H 0.4861 0.3199 1.0447 0.079 Uiso 1 1 calc R . .
C29 C 0.5712(2) 0.18075(16) 0.86488(16) 0.0337(4) Uani 1 1 d . . .
H29 H 0.5310 0.1676 0.9426 0.040 Uiso 1 1 calc R . .
C30 C 0.6412(2) 0.08705(16) 0.79129(17) 0.0359(4) Uani 1 1 d . . .
C31 C 0.7206(3) -0.12255(19) 0.7718(2) 0.0692(7) Uani 1 1 d . . .
H31A H 0.6674 -0.1099 0.7153 0.104 Uiso 1 1 calc R . .
H31B H 0.7181 -0.1939 0.8171 0.104 Uiso 1 1 calc R . .
H31C H 0.8253 -0.1324 0.7343 0.104 Uiso 1 1 calc R . .
C32 C 0.6992(2) 0.10425(16) 0.67609(17) 0.0359(4) Uani 1 1 d . . .
H32 H 0.7474 0.0395 0.6268 0.043 Uiso 1 1 calc R . .
C33 C 0.68420(19) 0.22056(15) 0.63507(15) 0.0293(4) Uani 1 1 d . . .
C34 C 0.8144(2) 0.15324(19) 0.44332(17) 0.0491(6) Uani 1 1 d . . .
H34A H 0.8439 0.1862 0.3678 0.074 Uiso 1 1 calc R . .
H34B H 0.7479 0.1131 0.4451 0.074 Uiso 1 1 calc R . .
H34C H 0.9043 0.0963 0.4633 0.074 Uiso 1 1 calc R . .
O1 O 0.80335(14) 0.41482(11) 0.74648(12) 0.0425(4) Uani 1 1 d . . .
H1A H 0.8324 0.3386 0.7324 0.051 Uiso 1 1 d R . .
O2 O 0.50104(14) 0.39051(11) 0.89051(10) 0.0356(3) Uani 1 1 d . . .
O3 O 0.64925(17) -0.02243(11) 0.84260(13) 0.0514(4) Uani 1 1 d . . .
O4 O 0.73641(14) 0.24770(11) 0.52245(10) 0.0389(3) Uani 1 1 d . . .
 
 
_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_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 O1 1.428(2) . ?
C1 C2 1.540(2) . ?
C1 C25 1.554(2) . ?
C1 H1 0.9900 . ?
C2 C9 1.517(2) . ?
C2 C3 1.523(2) . ?
C2 H2 0.9900 . ?
C3 C8 1.386(2) . ?
C3 C4 1.390(2) . ?
C4 C5 1.384(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.379(3) . ?
C6 H6 0.9400 . ?
C7 C8 1.385(3) . ?
C7 H7 0.9400 . ?
C8 H8 0.9400 . ?
C9 C18 1.346(2) . ?
C9 C10 1.426(2) . ?
C10 C11 1.202(2) . ?
C11 C12 1.434(2) . ?
C12 C13 1.393(3) . ?
C12 C17 1.395(2) . ?
C13 C14 1.375(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.379(3) . ?
C14 H14 0.9400 . ?
C15 C16 1.373(3) . ?
C15 H15 0.9400 . ?
C16 C17 1.385(3) . ?
C16 H16 0.9400 . ?
C17 H17 0.9400 . ?
C18 C19 1.474(2) . ?
C18 C25 1.522(2) . ?
C19 C20 1.394(2) . ?
C19 C24 1.395(2) . ?
C20 C21 1.386(3) . ?
C20 H20 0.9400 . ?
C21 C22 1.378(3) . ?
C21 H21 0.9400 . ?
C22 C23 1.377(3) . ?
C22 H22 0.9400 . ?
C23 C24 1.385(3) . ?
C23 H23 0.9400 . ?
C24 H24 0.9400 . ?
C25 C26 1.514(2) . ?
C25 H25 0.9900 . ?
C26 C33 1.395(2) . ?
C26 C27 1.409(2) . ?
C27 O2 1.362(2) . ?
C27 C29 1.386(2) . ?
C28 O2 1.421(2) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 H28C 0.9700 . ?
C29 C30 1.378(3) . ?
C29 H29 0.9400 . ?
C30 O3 1.376(2) . ?
C30 C32 1.386(3) . ?
C31 O3 1.415(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 H31C 0.9700 . ?
C32 C33 1.400(3) . ?
C32 H32 0.9400 . ?
C33 O4 1.374(2) . ?
C34 O4 1.427(2) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 H34C 0.9700 . ?
O1 H1A 0.8828 . ?
 
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
O1 C1 C2 106.83(14) . . ?
O1 C1 C25 113.07(13) . . ?
C2 C1 C25 106.02(13) . . ?
O1 C1 H1 110.3 . . ?
C2 C1 H1 110.3 . . ?
C25 C1 H1 110.3 . . ?
C9 C2 C3 114.80(14) . . ?
C9 C2 C1 103.75(13) . . ?
C3 C2 C1 114.51(13) . . ?
C9 C2 H2 107.8 . . ?
C3 C2 H2 107.8 . . ?
C1 C2 H2 107.8 . . ?
C8 C3 C4 118.37(16) . . ?
C8 C3 C2 122.58(15) . . ?
C4 C3 C2 119.05(15) . . ?
C5 C4 C3 120.93(18) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C6 C5 C4 119.95(18) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C7 C6 C5 119.73(18) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 120.22(19) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C3 120.76(18) . . ?
C7 C8 H8 119.6 . . ?
C3 C8 H8 119.6 . . ?
C18 C9 C10 127.11(16) . . ?
C18 C9 C2 112.86(14) . . ?
C10 C9 C2 120.01(14) . . ?
C11 C10 C9 177.26(18) . . ?
C10 C11 C12 175.91(19) . . ?
C13 C12 C17 118.89(16) . . ?
C13 C12 C11 120.53(16) . . ?
C17 C12 C11 120.53(16) . . ?
C14 C13 C12 120.25(18) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.46(19) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 120.01(18) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.27(19) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 120.09(18) . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?
C9 C18 C19 128.01(15) . . ?
C9 C18 C25 110.58(15) . . ?
C19 C18 C25 121.38(14) . . ?
C20 C19 C24 117.76(16) . . ?
C20 C19 C18 121.72(15) . . ?
C24 C19 C18 120.47(15) . . ?
C21 C20 C19 120.80(17) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C20 120.52(18) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C21 119.53(18) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 120.28(17) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 121.10(17) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
C26 C25 C18 116.62(14) . . ?
C26 C25 C1 113.83(14) . . ?
C18 C25 C1 104.26(13) . . ?
C26 C25 H25 107.2 . . ?
C18 C25 H25 107.2 . . ?
C1 C25 H25 107.2 . . ?
C33 C26 C27 116.78(15) . . ?
C33 C26 C25 120.25(15) . . ?
C27 C26 C25 122.97(15) . . ?
O2 C27 C29 122.54(16) . . ?
O2 C27 C26 115.44(15) . . ?
C29 C27 C26 122.00(16) . . ?
O2 C28 H28A 109.5 . . ?
O2 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O2 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 C27 119.00(17) . . ?
C30 C29 H29 120.5 . . ?
C27 C29 H29 120.5 . . ?
O3 C30 C29 114.19(17) . . ?
O3 C30 C32 124.15(17) . . ?
C29 C30 C32 121.66(17) . . ?
O3 C31 H31A 109.5 . . ?
O3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 C33 118.25(16) . . ?
C30 C32 H32 120.9 . . ?
C33 C32 H32 120.9 . . ?
O4 C33 C26 114.73(15) . . ?
O4 C33 C32 123.01(16) . . ?
C26 C33 C32 122.27(17) . . ?
O4 C34 H34A 109.5 . . ?
O4 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O4 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C1 O1 H1A 103.1 . . ?
C27 O2 C28 118.96(14) . . ?
C30 O3 C31 117.02(17) . . ?
C33 O4 C34 119.08(15) . . ?
 
_diffrn_measured_fraction_theta_max    0.985
_diffrn_reflns_theta_full              25.25
_diffrn_measured_fraction_theta_full   0.985
_refine_diff_density_max    0.282
_refine_diff_density_min   -0.185
_refine_diff_density_rms    0.035
