# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c235
_audit_block_doi                 10.5517/ccyd0p0
_database_code_depnum_ccdc_archive 'CCDC 875492'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/adsc.201300893 2014
_audit_update_record             
;
2012-04-11 deposited with the CCDC.
2016-03-07 downloaded from the CCDC.
;
#TrackingRef 'web_deposit_cif_file_0_jianwang_1334114234.C235.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H24 O3'
_chemical_formula_weight         516.56

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                   6.3266(6)
_cell_length_b                   11.3868(11)
_cell_length_c                   18.6894(19)
_cell_angle_alpha                94.305(2)
_cell_angle_beta                 99.144(2)
_cell_angle_gamma                100.166(2)
_cell_volume                     1301.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7594
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      28.29

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             540
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9521
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17120
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.11
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5964
_reflns_number_gt                5249
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0830P)²+0.4563P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5964
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1432
_refine_ls_wR_factor_gt          0.1316
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
O1 O 0.20070(16) 0.52467(9) 0.36460(5) 0.0229(2) Uani 1 1 d . . .
O2 O -0.02250(16) 0.39041(9) 0.28499(6) 0.0267(2) Uani 1 1 d . . .
O3 O 0.65848(16) 0.31602(9) 0.37834(5) 0.0247(2) Uani 1 1 d . . .
C1 C 0.4063(2) 0.56961(12) 0.40437(7) 0.0194(3) Uani 1 1 d . . .
C2 C 0.4321(2) 0.68081(13) 0.44461(8) 0.0248(3) Uani 1 1 d . . .
H2 H 0.3136 0.7220 0.4428 0.030 Uiso 1 1 calc R . .
C3 C 0.6317(3) 0.73057(13) 0.48715(8) 0.0262(3) Uani 1 1 d . . .
H3 H 0.6508 0.8064 0.5147 0.031 Uiso 1 1 calc R . .
C4 C 0.8056(3) 0.66955(13) 0.48976(8) 0.0277(3) Uani 1 1 d . . .
H4 H 0.9431 0.7043 0.5187 0.033 Uiso 1 1 calc R . .
C5 C 0.7776(2) 0.55857(13) 0.45031(8) 0.0243(3) Uani 1 1 d . . .
H5 H 0.8957 0.5170 0.4523 0.029 Uiso 1 1 calc R . .
C6 C 0.5772(2) 0.50794(12) 0.40778(7) 0.0211(3) Uani 1 1 d . . .
C7 C 0.5439(2) 0.38882(12) 0.36568(7) 0.0195(3) Uani 1 1 d . . .
C8 C 0.3533(2) 0.36732(11) 0.30169(7) 0.0191(3) Uani 1 1 d . . .
C9 C 0.1591(2) 0.42438(12) 0.31606(7) 0.0206(3) Uani 1 1 d . . .
C10 C 0.2832(2) 0.23673(11) 0.27256(7) 0.0191(3) Uani 1 1 d . . .
C11 C 0.3271(2) 0.22159(11) 0.20477(7) 0.0181(3) Uani 1 1 d . . .
C12 C 0.4278(2) 0.33855(11) 0.18361(7) 0.0182(3) Uani 1 1 d . . .
C13 C 0.4399(2) 0.42609(12) 0.23730(7) 0.0189(3) Uani 1 1 d . . .
C14 C 0.2081(2) 0.14177(11) 0.31764(7) 0.0200(3) Uani 1 1 d . . .
C15 C 0.0164(2) 0.13591(13) 0.34641(7) 0.0230(3) Uani 1 1 d . . .
H15 H -0.0727 0.1939 0.3368 0.028 Uiso 1 1 calc R . .
C16 C -0.0442(3) 0.04496(14) 0.38922(8) 0.0282(3) Uani 1 1 d . . .
H16 H -0.1748 0.0412 0.4087 0.034 Uiso 1 1 calc R . .
C17 C 0.0840(3) -0.03975(13) 0.40357(9) 0.0320(3) Uani 1 1 d . . .
H17 H 0.0421 -0.1012 0.4330 0.038 Uiso 1 1 calc R . .
C18 C 0.2742(3) -0.03483(14) 0.37486(9) 0.0330(3) Uani 1 1 d . . .
H18 H 0.3624 -0.0932 0.3845 0.040 Uiso 1 1 calc R . .
C19 C 0.3357(3) 0.05515(13) 0.33207(8) 0.0273(3) Uani 1 1 d . . .
H19 H 0.4658 0.0579 0.3124 0.033 Uiso 1 1 calc R . .
C20 C 0.2747(2) 0.10786(11) 0.15648(7) 0.0194(3) Uani 1 1 d . . .
C21 C 0.4287(2) 0.06661(12) 0.12051(8) 0.0238(3) Uani 1 1 d . . .
H21 H 0.5729 0.1119 0.1270 0.029 Uiso 1 1 calc R . .
C22 C 0.3717(3) -0.04045(13) 0.07519(8) 0.0311(3) Uani 1 1 d . . .
H22 H 0.4780 -0.0690 0.0516 0.037 Uiso 1 1 calc R . .
C23 C 0.1615(3) -0.10562(14) 0.06418(9) 0.0358(4) Uani 1 1 d . . .
H23 H 0.1227 -0.1781 0.0324 0.043 Uiso 1 1 calc R . .
C24 C 0.0074(3) -0.06547(14) 0.09943(10) 0.0370(4) Uani 1 1 d . . .
H24 H -0.1372 -0.1105 0.0920 0.044 Uiso 1 1 calc R . .
C25 C 0.0638(2) 0.04035(13) 0.14549(9) 0.0276(3) Uani 1 1 d . . .
H25 H -0.0425 0.0672 0.1699 0.033 Uiso 1 1 calc R . .
C26 C 0.5045(2) 0.35390(11) 0.11350(7) 0.0185(3) Uani 1 1 d . . .
C27 C 0.3629(2) 0.32061(12) 0.04720(8) 0.0241(3) Uani 1 1 d . . .
H27 H 0.2135 0.2882 0.0465 0.029 Uiso 1 1 calc R . .
C28 C 0.4393(3) 0.33468(13) -0.01791(8) 0.0289(3) Uani 1 1 d . . .
H28 H 0.3414 0.3132 -0.0630 0.035 Uiso 1 1 calc R . .
C29 C 0.6573(3) 0.37988(13) -0.01744(8) 0.0302(3) Uani 1 1 d . . .
H29 H 0.7091 0.3893 -0.0621 0.036 Uiso 1 1 calc R . .
C30 C 0.7996(3) 0.41133(14) 0.04808(9) 0.0302(3) Uani 1 1 d . . .
H30 H 0.9498 0.4415 0.0484 0.036 Uiso 1 1 calc R . .
C31 C 0.7239(2) 0.39892(13) 0.11338(8) 0.0243(3) Uani 1 1 d . . .
H31 H 0.8224 0.4213 0.1583 0.029 Uiso 1 1 calc R . .
C32 C 0.5026(2) 0.55810(11) 0.23694(7) 0.0193(3) Uani 1 1 d . . .
C33 C 0.3418(2) 0.62508(13) 0.21747(8) 0.0243(3) Uani 1 1 d . . .
H33 H 0.1937 0.5857 0.2039 0.029 Uiso 1 1 calc R . .
C34 C 0.3963(3) 0.74895(13) 0.21768(8) 0.0296(3) Uani 1 1 d . . .
H34 H 0.2855 0.7938 0.2046 0.036 Uiso 1 1 calc R . .
C35 C 0.6115(3) 0.80660(13) 0.23689(9) 0.0309(3) Uani 1 1 d . . .
H35 H 0.6490 0.8911 0.2367 0.037 Uiso 1 1 calc R . .
C36 C 0.7722(3) 0.74143(14) 0.25644(9) 0.0315(3) Uani 1 1 d . . .
H36 H 0.9200 0.7813 0.2697 0.038 Uiso 1 1 calc R . .
C37 C 0.7187(2) 0.61783(13) 0.25687(8) 0.0256(3) Uani 1 1 d . . .
H37 H 0.8301 0.5738 0.2708 0.031 Uiso 1 1 calc R . .


_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
O1 C9 1.3634(16) . ?
O1 C1 1.3809(17) . ?
O2 C9 1.1850(18) . ?
O3 C7 1.2064(17) . ?
C1 C6 1.3856(19) . ?
C1 C2 1.3931(19) . ?
C2 C3 1.382(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.4797(19) . ?
C7 C8 1.5293(19) . ?
C8 C10 1.5077(17) . ?
C8 C9 1.5373(19) . ?
C8 C13 1.5485(17) . ?
C10 C11 1.3445(18) . ?
C10 C14 1.4790(18) . ?
C11 C20 1.4763(18) . ?
C11 C12 1.4818(18) . ?
C12 C13 1.3433(18) . ?
C12 C26 1.4798(17) . ?
C13 C32 1.4862(18) . ?
C14 C19 1.396(2) . ?
C14 C15 1.3961(19) . ?
C15 C16 1.393(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.3931(19) . ?
C20 C21 1.3940(19) . ?
C21 C22 1.388(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.379(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C27 1.3922(19) . ?
C26 C31 1.3927(19) . ?
C27 C28 1.389(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.383(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.381(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.388(2) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C37 1.394(2) . ?
C32 C33 1.395(2) . ?
C33 C34 1.391(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.381(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.381(2) . ?
C35 H35 0.9500 . ?
C36 C37 1.389(2) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?

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
C9 O1 C1 122.01(11) . . ?
O1 C1 C6 123.43(12) . . ?
O1 C1 C2 115.88(12) . . ?
C6 C1 C2 120.63(13) . . ?
C3 C2 C1 119.37(13) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.15(13) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.05(14) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.04(14) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.75(13) . . ?
C1 C6 C7 119.50(12) . . ?
C5 C6 C7 120.76(12) . . ?
O3 C7 C6 124.14(12) . . ?
O3 C7 C8 122.32(12) . . ?
C6 C7 C8 113.50(11) . . ?
C10 C8 C7 112.49(11) . . ?
C10 C8 C9 112.06(11) . . ?
C7 C8 C9 114.32(11) . . ?
C10 C8 C13 103.14(10) . . ?
C7 C8 C13 106.98(10) . . ?
C9 C8 C13 106.92(10) . . ?
O2 C9 O1 117.87(12) . . ?
O2 C9 C8 124.19(12) . . ?
O1 C9 C8 117.82(12) . . ?
C11 C10 C14 127.09(12) . . ?
C11 C10 C8 109.27(11) . . ?
C14 C10 C8 123.12(11) . . ?
C10 C11 C20 125.99(12) . . ?
C10 C11 C12 109.64(11) . . ?
C20 C11 C12 124.31(11) . . ?
C13 C12 C26 125.97(12) . . ?
C13 C12 C11 110.04(11) . . ?
C26 C12 C11 123.99(11) . . ?
C12 C13 C32 128.98(12) . . ?
C12 C13 C8 107.83(11) . . ?
C32 C13 C8 122.96(11) . . ?
C19 C14 C15 119.02(12) . . ?
C19 C14 C10 118.28(12) . . ?
C15 C14 C10 122.69(12) . . ?
C16 C15 C14 119.94(13) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.55(14) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 119.83(14) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 120.08(15) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 120.58(14) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C25 C20 C21 118.81(13) . . ?
C25 C20 C11 119.05(12) . . ?
C21 C20 C11 122.13(12) . . ?
C22 C21 C20 120.14(14) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 120.39(14) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 119.96(14) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C25 119.99(15) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C20 120.69(14) . . ?
C24 C25 H25 119.7 . . ?
C20 C25 H25 119.7 . . ?
C27 C26 C31 119.01(12) . . ?
C27 C26 C12 121.31(12) . . ?
C31 C26 C12 119.64(12) . . ?
C28 C27 C26 120.25(14) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C29 C28 C27 120.28(14) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C30 C29 C28 119.85(13) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C29 C30 C31 120.18(14) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C30 C31 C26 120.41(14) . . ?
C30 C31 H31 119.8 . . ?
C26 C31 H31 119.8 . . ?
C37 C32 C33 118.68(12) . . ?
C37 C32 C13 121.70(12) . . ?
C33 C32 C13 119.62(12) . . ?
C34 C33 C32 120.65(14) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C35 C34 C33 119.94(14) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C36 C35 C34 120.00(14) . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C36 C37 120.36(15) . . ?
C35 C36 H36 119.8 . . ?
C37 C36 H36 119.8 . . ?
C36 C37 C32 120.37(14) . . ?
C36 C37 H37 119.8 . . ?
C32 C37 H37 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.087


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c649
_database_code_depnum_ccdc_archive 'CCDC 915903'
_audit_update_record             
;
2012-12-16 deposited with the CCDC.
2016-03-07 downloaded from the CCDC.
;
#TrackingRef 'web_deposit_cif_file_0_jianwang_1355639419.C649.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H26 O2'
_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                   6.5140(9)
_cell_length_b                   11.9444(16)
_cell_length_c                   17.215(2)
_cell_angle_alpha                93.280(3)
_cell_angle_beta                 94.949(3)
_cell_angle_gamma                104.241(3)
_cell_volume                     1289.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    979
_cell_measurement_theta_min      3.28
_cell_measurement_theta_max      27.19

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8127
_exptl_absorpt_correction_T_max  0.9422
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17084
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5932
_reflns_number_gt                4921
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0618P)²+0.3242P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5932
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1179
_refine_ls_wR_factor_gt          0.1126
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
O1 O 0.39008(14) 0.16693(8) 0.17437(5) 0.0175(2) Uani 1 1 d . . .
H1 H 0.2759 0.1404 0.1453 0.026 Uiso 1 1 calc R . .
O2 O 0.99517(13) 0.07678(7) 0.09390(5) 0.01594(19) Uani 1 1 d . . .
C1 C 0.55203(19) 0.20599(10) 0.05430(7) 0.0130(2) Uani 1 1 d . . .
C2 C 0.4061(2) 0.21502(11) -0.00760(7) 0.0157(3) Uani 1 1 d . . .
H2 H 0.3011 0.2560 0.0010 0.019 Uiso 1 1 calc R . .
C3 C 0.4127(2) 0.16460(11) -0.08174(7) 0.0169(3) Uani 1 1 d . . .
H3 H 0.3105 0.1696 -0.1233 0.020 Uiso 1 1 calc R . .
C4 C 0.5689(2) 0.10681(11) -0.09518(7) 0.0162(3) Uani 1 1 d . . .
H4 H 0.5735 0.0729 -0.1461 0.019 Uiso 1 1 calc R . .
C5 C 0.7174(2) 0.09850(10) -0.03493(7) 0.0148(2) Uani 1 1 d . . .
H5 H 0.8253 0.0600 -0.0445 0.018 Uiso 1 1 calc R . .
C6 C 0.70823(18) 0.14697(10) 0.04008(7) 0.0126(2) Uani 1 1 d . . .
C7 C 0.86043(18) 0.13099(10) 0.10516(7) 0.0124(2) Uani 1 1 d . . .
C8 C 0.83894(18) 0.18291(10) 0.18192(7) 0.0122(2) Uani 1 1 d . . .
C9 C 0.74810(19) 0.28836(10) 0.18754(7) 0.0131(2) Uani 1 1 d . . .
C10 C 0.52942(19) 0.25191(10) 0.13618(7) 0.0132(2) Uani 1 1 d . . .
H10 H 0.4695 0.3211 0.1326 0.016 Uiso 1 1 calc R . .
C11 C 0.72011(19) 0.29961(11) 0.27451(7) 0.0144(2) Uani 1 1 d . . .
C12 C 0.77150(19) 0.21015(11) 0.30934(7) 0.0145(2) Uani 1 1 d . . .
C13 C 0.84071(18) 0.13520(10) 0.25131(7) 0.0135(2) Uani 1 1 d . . .
C14 C 0.88347(19) 0.39711(10) 0.15682(7) 0.0143(2) Uani 1 1 d . . .
C15 C 1.0749(2) 0.39721(11) 0.12639(8) 0.0178(3) Uani 1 1 d . . .
H15 H 1.1265 0.3295 0.1273 0.021 Uiso 1 1 calc R . .
C16 C 1.1919(2) 0.49422(12) 0.09477(8) 0.0233(3) Uani 1 1 d . . .
H16 H 1.3218 0.4922 0.0743 0.028 Uiso 1 1 calc R . .
C17 C 1.1195(2) 0.59358(12) 0.09308(8) 0.0237(3) Uani 1 1 d . . .
H17 H 1.1984 0.6599 0.0711 0.028 Uiso 1 1 calc R . .
C18 C 0.9309(2) 0.59560(12) 0.12379(8) 0.0225(3) Uani 1 1 d . . .
H18 H 0.8813 0.6640 0.1232 0.027 Uiso 1 1 calc R . .
C19 C 0.8135(2) 0.49891(11) 0.15542(8) 0.0191(3) Uani 1 1 d . . .
H19 H 0.6844 0.5018 0.1763 0.023 Uiso 1 1 calc R . .
C20 C 0.6448(2) 0.39267(11) 0.31463(7) 0.0181(3) Uani 1 1 d . . .
C21 C 0.4433(2) 0.40847(13) 0.29335(8) 0.0261(3) Uani 1 1 d . . .
H21 H 0.3556 0.3616 0.2507 0.031 Uiso 1 1 calc R . .
C22 C 0.3689(3) 0.49184(15) 0.33373(10) 0.0353(4) Uani 1 1 d . . .
H22 H 0.2318 0.5022 0.3181 0.042 Uiso 1 1 calc R . .
C23 C 0.4924(3) 0.55950(13) 0.39632(10) 0.0376(4) Uani 1 1 d . . .
H23 H 0.4402 0.6157 0.4244 0.045 Uiso 1 1 calc R . .
C24 C 0.6933(3) 0.54516(13) 0.41818(9) 0.0346(4) Uani 1 1 d . . .
H24 H 0.7793 0.5921 0.4612 0.041 Uiso 1 1 calc R . .
C25 C 0.7705(2) 0.46241(12) 0.37763(8) 0.0245(3) Uani 1 1 d . . .
H25 H 0.9089 0.4535 0.3929 0.029 Uiso 1 1 calc R . .
C26 C 0.7510(2) 0.18492(11) 0.39196(7) 0.0156(3) Uani 1 1 d . . .
C27 C 0.5614(2) 0.18395(12) 0.42416(8) 0.0192(3) Uani 1 1 d . . .
H27 H 0.4465 0.2007 0.3931 0.023 Uiso 1 1 calc R . .
C28 C 0.5389(2) 0.15883(12) 0.50106(8) 0.0222(3) Uani 1 1 d . . .
H28 H 0.4089 0.1581 0.5224 0.027 Uiso 1 1 calc R . .
C29 C 0.7059(2) 0.13485(12) 0.54670(8) 0.0240(3) Uani 1 1 d . . .
H29 H 0.6910 0.1184 0.5996 0.029 Uiso 1 1 calc R . .
C30 C 0.8944(2) 0.13480(13) 0.51547(8) 0.0252(3) Uani 1 1 d . . .
H30 H 1.0089 0.1183 0.5469 0.030 Uiso 1 1 calc R . .
C31 C 0.9169(2) 0.15873(12) 0.43827(8) 0.0211(3) Uani 1 1 d . . .
H31 H 1.0459 0.1573 0.4168 0.025 Uiso 1 1 calc R . .
C32 C 0.85776(19) 0.01619(11) 0.26575(7) 0.0142(2) Uani 1 1 d . . .
C33 C 1.0341(2) -0.02558(11) 0.25176(7) 0.0171(3) Uani 1 1 d . . .
H33 H 1.1575 0.0249 0.2359 0.021 Uiso 1 1 calc R . .
C34 C 1.0298(2) -0.14114(12) 0.26107(8) 0.0201(3) Uani 1 1 d . . .
H34 H 1.1500 -0.1693 0.2509 0.024 Uiso 1 1 calc R . .
C35 C 0.8519(2) -0.21552(11) 0.28500(7) 0.0206(3) Uani 1 1 d . . .
H35 H 0.8495 -0.2944 0.2908 0.025 Uiso 1 1 calc R . .
C36 C 0.6769(2) -0.17404(11) 0.30043(7) 0.0200(3) Uani 1 1 d . . .
H36 H 0.5547 -0.2245 0.3171 0.024 Uiso 1 1 calc R . .
C37 C 0.6805(2) -0.05892(11) 0.29152(7) 0.0164(3) Uani 1 1 d . . .
H37 H 0.5613 -0.0307 0.3030 0.020 Uiso 1 1 calc R . .


_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
O1 C10 1.4187(14) . ?
O2 C7 1.2336(14) . ?
C1 C2 1.3927(17) . ?
C1 C6 1.4031(17) . ?
C1 C10 1.5154(16) . ?
C2 C3 1.3886(18) . ?
C3 C4 1.3901(18) . ?
C4 C5 1.3811(17) . ?
C5 C6 1.3968(17) . ?
C6 C7 1.4834(16) . ?
C7 C8 1.4599(16) . ?
C8 C13 1.3529(17) . ?
C8 C9 1.5194(16) . ?
C9 C11 1.5262(16) . ?
C9 C14 1.5298(17) . ?
C9 C10 1.5601(16) . ?
C11 C12 1.3521(17) . ?
C11 C20 1.4805(17) . ?
C12 C13 1.4754(17) . ?
C12 C26 1.4811(17) . ?
C13 C32 1.4860(17) . ?
C14 C15 1.3933(18) . ?
C14 C19 1.4003(17) . ?
C15 C16 1.3888(19) . ?
C16 C17 1.381(2) . ?
C17 C18 1.384(2) . ?
C18 C19 1.3872(19) . ?
C20 C21 1.393(2) . ?
C20 C25 1.396(2) . ?
C21 C22 1.388(2) . ?
C22 C23 1.376(3) . ?
C23 C24 1.385(3) . ?
C24 C25 1.394(2) . ?
C26 C27 1.3947(18) . ?
C26 C31 1.3958(18) . ?
C27 C28 1.3861(18) . ?
C28 C29 1.383(2) . ?
C29 C30 1.383(2) . ?
C30 C31 1.3878(19) . ?
C32 C33 1.3939(18) . ?
C32 C37 1.3997(18) . ?
C33 C34 1.3924(18) . ?
C34 C35 1.3857(19) . ?
C35 C36 1.3893(19) . ?
C36 C37 1.3870(18) . ?

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 C1 C6 118.83(11) . . ?
C2 C1 C10 119.65(11) . . ?
C6 C1 C10 121.37(11) . . ?
C3 C2 C1 120.53(11) . . ?
C2 C3 C4 120.08(11) . . ?
C5 C4 C3 120.33(11) . . ?
C4 C5 C6 119.69(11) . . ?
C5 C6 C1 120.50(11) . . ?
C5 C6 C7 119.03(11) . . ?
C1 C6 C7 120.42(11) . . ?
O2 C7 C8 123.10(11) . . ?
O2 C7 C6 121.16(11) . . ?
C8 C7 C6 115.75(10) . . ?
C13 C8 C7 127.99(11) . . ?
C13 C8 C9 110.43(10) . . ?
C7 C8 C9 119.60(10) . . ?
C8 C9 C11 101.63(9) . . ?
C8 C9 C14 114.81(10) . . ?
C11 C9 C14 114.78(10) . . ?
C8 C9 C10 105.16(9) . . ?
C11 C9 C10 111.72(10) . . ?
C14 C9 C10 108.30(10) . . ?
O1 C10 C1 110.97(10) . . ?
O1 C10 C9 107.81(9) . . ?
C1 C10 C9 111.70(10) . . ?
C12 C11 C20 125.02(11) . . ?
C12 C11 C9 109.45(11) . . ?
C20 C11 C9 125.52(11) . . ?
C11 C12 C13 109.80(11) . . ?
C11 C12 C26 126.21(11) . . ?
C13 C12 C26 123.90(11) . . ?
C8 C13 C12 108.37(11) . . ?
C8 C13 C32 127.42(11) . . ?
C12 C13 C32 122.80(11) . . ?
C15 C14 C19 117.76(12) . . ?
C15 C14 C9 121.55(11) . . ?
C19 C14 C9 120.64(11) . . ?
C16 C15 C14 121.42(12) . . ?
C17 C16 C15 120.11(13) . . ?
C16 C17 C18 119.33(13) . . ?
C17 C18 C19 120.77(13) . . ?
C18 C19 C14 120.61(12) . . ?
C21 C20 C25 118.57(13) . . ?
C21 C20 C11 120.96(12) . . ?
C25 C20 C11 120.38(12) . . ?
C22 C21 C20 120.81(15) . . ?
C23 C22 C21 120.41(16) . . ?
C22 C23 C24 119.55(14) . . ?
C23 C24 C25 120.55(15) . . ?
C24 C25 C20 120.09(15) . . ?
C27 C26 C31 118.81(12) . . ?
C27 C26 C12 120.02(11) . . ?
C31 C26 C12 121.15(11) . . ?
C28 C27 C26 120.62(12) . . ?
C29 C28 C27 119.98(13) . . ?
C30 C29 C28 120.08(12) . . ?
C29 C30 C31 120.17(13) . . ?
C30 C31 C26 120.33(13) . . ?
C33 C32 C37 118.86(11) . . ?
C33 C32 C13 123.98(11) . . ?
C37 C32 C13 117.10(11) . . ?
C34 C33 C32 120.10(12) . . ?
C35 C34 C33 120.63(12) . . ?
C34 C35 C36 119.62(12) . . ?
C37 C36 C35 120.03(12) . . ?
C36 C37 C32 120.73(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.84 1.91 2.7473(13) 171.1 1_455

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.051


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c686
_database_code_depnum_ccdc_archive 'CCDC 925571'
_audit_update_record             
;
2013-02-20 deposited with the CCDC.
2016-03-07 downloaded from the CCDC.
;
#TrackingRef 'web_deposit_cif_file_0_JianWang_1361330470.C686.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H27 N O3.50'
_chemical_formula_weight         553.61

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'

_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                   12.8713(7)
_cell_length_b                   12.9061(8)
_cell_length_c                   18.4438(11)
_cell_angle_alpha                83.4910(10)
_cell_angle_beta                 70.2210(10)
_cell_angle_gamma                87.1970(10)
_cell_volume                     2864.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4715
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.49

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1160
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6415
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20371
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0633
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.18
_diffrn_reflns_theta_max         27.50
_reflns_number_total             13089
_reflns_number_gt                10144
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0836P)²+0.6911P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         13089
_refine_ls_number_parameters     803
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1640
_refine_ls_wR_factor_gt          0.1486
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_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
H6O H 0.2447(16) 0.076(2) 0.4420(13) 0.036(7) Uiso 1 1 d D . .
H3O H 0.559(2) 0.4905(19) 0.8381(11) 0.036(7) Uiso 1 1 d D . .
O1X O -0.0760(2) -0.0965(2) -0.01509(19) 0.0331(6) Uani 0.50 1 d PDU A -1
O2X O 0.0254(3) 0.0288(2) 0.00306(19) 0.0310(5) Uani 0.50 1 d PDU A -1
C1X C 0.1151(4) -0.0791(4) -0.0954(3) 0.0332(7) Uani 0.50 1 d PDU A -1
H1X1 H 0.1030 -0.1402 -0.1184 0.050 Uiso 0.50 1 calc PR A -1
H1X2 H 0.1739 -0.0946 -0.0730 0.050 Uiso 0.50 1 calc PR A -1
H1X3 H 0.1367 -0.0199 -0.1354 0.050 Uiso 0.50 1 calc PR A -1
C2X C 0.0105(4) -0.0522(4) -0.0330(3) 0.0321(6) Uani 0.50 1 d PDU A -1
C3X C -0.0692(4) 0.0584(4) 0.0648(3) 0.0304(6) Uani 0.50 1 d PDU A -1
H3X1 H -0.0925 -0.0003 0.1060 0.036 Uiso 0.50 1 calc PR A -1
H3X2 H -0.1313 0.0775 0.0455 0.036 Uiso 0.50 1 calc PR A -1
C4X C -0.0380(4) 0.1508(3) 0.0966(3) 0.0305(7) Uani 0.50 1 d PDU A -1
H4X1 H 0.0288 0.1338 0.1099 0.046 Uiso 0.50 1 calc PR A -1
H4X2 H -0.0985 0.1673 0.1431 0.046 Uiso 0.50 1 calc PR A -1
H4X3 H -0.0241 0.2112 0.0574 0.046 Uiso 0.50 1 calc PR A -1
O1 O 0.08616(12) 0.38383(13) 1.01969(10) 0.0352(4) Uani 1 1 d . . .
O2 O 0.37794(12) 0.43933(12) 1.09786(8) 0.0252(3) Uani 1 1 d . . .
O3 O 0.53898(11) 0.46667(11) 0.80313(8) 0.0191(3) Uani 1 1 d D . .
O4 O 0.00122(12) 0.03056(13) 0.78651(8) 0.0281(3) Uani 1 1 d . . .
O5 O -0.12105(11) -0.04941(11) 0.59462(8) 0.0234(3) Uani 1 1 d . . .
O6 O 0.29202(10) 0.08638(10) 0.46343(7) 0.0146(3) Uani 1 1 d D . .
N1 N 0.25137(13) 0.41020(12) 1.03896(9) 0.0173(3) Uani 1 1 d . . .
N2 N -0.03342(12) -0.00534(11) 0.67696(8) 0.0133(3) Uani 1 1 d . . .
C1 C 0.13840(16) 0.38435(16) 1.06286(12) 0.0237(4) Uani 1 1 d . . .
C2 C 0.10402(17) 0.36035(17) 1.14791(12) 0.0262(5) Uani 1 1 d . . .
C3 C 0.00258(19) 0.3270(2) 1.20029(15) 0.0393(6) Uani 1 1 d . . .
H3A H -0.0584 0.3170 1.1839 0.047 Uiso 1 1 calc R . .
C4 C -0.0055(2) 0.3092(2) 1.27739(15) 0.0455(7) Uani 1 1 d . . .
H4 H -0.0734 0.2855 1.3148 0.055 Uiso 1 1 calc R . .
C5 C 0.0828(2) 0.32501(18) 1.30102(13) 0.0406(7) Uani 1 1 d . . .
H5 H 0.0742 0.3119 1.3545 0.049 Uiso 1 1 calc R . .
C6 C 0.1839(2) 0.35959(17) 1.24903(12) 0.0310(5) Uani 1 1 d . . .
H6A H 0.2443 0.3710 1.2656 0.037 Uiso 1 1 calc R . .
C7 C 0.19203(17) 0.37659(15) 1.17192(11) 0.0218(4) Uani 1 1 d . . .
C8 C 0.28726(16) 0.41239(15) 1.10240(11) 0.0183(4) Uani 1 1 d . . .
C9 C 0.31317(15) 0.45128(15) 0.96255(11) 0.0159(4) Uani 1 1 d . . .
C10 C 0.37296(15) 0.39689(14) 0.90454(10) 0.0149(4) Uani 1 1 d . . .
C11 C 0.42185(15) 0.47541(14) 0.83350(10) 0.0153(4) Uani 1 1 d . . .
C12 C 0.38158(15) 0.58132(14) 0.86375(11) 0.0157(4) Uani 1 1 d . . .
C13 C 0.31876(15) 0.56508(15) 0.93921(11) 0.0162(4) Uani 1 1 d . . .
C14 C 0.25976(16) 0.64130(15) 0.99377(11) 0.0191(4) Uani 1 1 d . . .
C15 C 0.14454(17) 0.64470(17) 1.02136(13) 0.0286(5) Uani 1 1 d . . .
H15 H 0.1042 0.5963 1.0064 0.034 Uiso 1 1 calc R . .
C16 C 0.0885(2) 0.7182(2) 1.07042(14) 0.0379(6) Uani 1 1 d . . .
H16 H 0.0101 0.7198 1.0893 0.045 Uiso 1 1 calc R . .
C17 C 0.1467(2) 0.7888(2) 1.09174(14) 0.0404(6) Uani 1 1 d . . .
H17 H 0.1084 0.8399 1.1246 0.048 Uiso 1 1 calc R . .
C18 C 0.2614(2) 0.78555(19) 1.06529(14) 0.0358(6) Uani 1 1 d . . .
H18 H 0.3013 0.8344 1.0801 0.043 Uiso 1 1 calc R . .
C19 C 0.31758(18) 0.71108(17) 1.01738(12) 0.0256(5) Uani 1 1 d . . .
H19 H 0.3959 0.7077 1.0006 0.031 Uiso 1 1 calc R . .
C20 C 0.40477(16) 0.67829(15) 0.81132(11) 0.0180(4) Uani 1 1 d . . .
C21 C 0.34213(17) 0.76948(16) 0.82977(12) 0.0235(4) Uani 1 1 d . . .
H21 H 0.2834 0.7694 0.8778 0.028 Uiso 1 1 calc R . .
C22 C 0.36456(19) 0.85976(16) 0.77911(13) 0.0276(5) Uani 1 1 d . . .
H22 H 0.3214 0.9209 0.7930 0.033 Uiso 1 1 calc R . .
C23 C 0.44906(19) 0.86209(16) 0.70842(12) 0.0265(5) Uani 1 1 d . . .
H23 H 0.4649 0.9246 0.6743 0.032 Uiso 1 1 calc R . .
C24 C 0.50988(18) 0.77246(16) 0.68817(12) 0.0237(4) Uani 1 1 d . . .
H24 H 0.5667 0.7729 0.6392 0.028 Uiso 1 1 calc R . .
C25 C 0.48873(17) 0.68135(15) 0.73878(11) 0.0205(4) Uani 1 1 d . . .
H25 H 0.5317 0.6204 0.7240 0.025 Uiso 1 1 calc R . .
C26 C 0.37317(15) 0.45594(14) 0.77143(11) 0.0157(4) Uani 1 1 d . . .
C27 C 0.26038(17) 0.47108(17) 0.78630(12) 0.0247(4) Uani 1 1 d . . .
H27 H 0.2148 0.4913 0.8351 0.030 Uiso 1 1 calc R . .
C28 C 0.21432(19) 0.45684(18) 0.73042(13) 0.0290(5) Uani 1 1 d . . .
H28 H 0.1373 0.4680 0.7409 0.035 Uiso 1 1 calc R . .
C29 C 0.27910(18) 0.42671(16) 0.65984(12) 0.0246(4) Uani 1 1 d . . .
H29 H 0.2473 0.4177 0.6214 0.030 Uiso 1 1 calc R . .
C30 C 0.39077(18) 0.40962(16) 0.64523(12) 0.0241(4) Uani 1 1 d . . .
H30 H 0.4358 0.3881 0.5967 0.029 Uiso 1 1 calc R . .
C31 C 0.43747(17) 0.42374(15) 0.70110(11) 0.0202(4) Uani 1 1 d . . .
H31 H 0.5142 0.4111 0.6908 0.024 Uiso 1 1 calc R . .
C32 C 0.38810(17) 0.28361(15) 0.90182(11) 0.0199(4) Uani 1 1 d . . .
C33 C 0.29686(19) 0.21797(17) 0.92709(12) 0.0270(5) Uani 1 1 d . . .
H33 H 0.2247 0.2468 0.9472 0.032 Uiso 1 1 calc R . .
C34 C 0.3103(2) 0.11117(18) 0.92313(14) 0.0385(6) Uani 1 1 d . . .
H34 H 0.2476 0.0674 0.9403 0.046 Uiso 1 1 calc R . .
C35 C 0.4159(3) 0.06803(18) 0.89394(15) 0.0433(7) Uani 1 1 d . . .
H35 H 0.4255 -0.0051 0.8915 0.052 Uiso 1 1 calc R . .
C36 C 0.5057(2) 0.13212(18) 0.86886(14) 0.0374(6) Uani 1 1 d . . .
H36 H 0.5777 0.1029 0.8487 0.045 Uiso 1 1 calc R . .
C37 C 0.49323(19) 0.23895(16) 0.87247(12) 0.0264(5) Uani 1 1 d . . .
H37 H 0.5565 0.2821 0.8549 0.032 Uiso 1 1 calc R . .
C38 C -0.05800(15) -0.00515(15) 0.75739(11) 0.0178(4) Uani 1 1 d . . .
C39 C -0.16820(15) -0.05411(15) 0.79395(11) 0.0175(4) Uani 1 1 d . . .
C40 C -0.23160(17) -0.07678(18) 0.87086(12) 0.0267(5) Uani 1 1 d . . .
H40 H -0.2064 -0.0615 0.9113 0.032 Uiso 1 1 calc R . .
C41 C -0.33339(17) -0.12260(17) 0.88692(12) 0.0258(5) Uani 1 1 d . . .
H41 H -0.3786 -0.1392 0.9393 0.031 Uiso 1 1 calc R . .
C42 C -0.37010(16) -0.14457(16) 0.82804(12) 0.0236(4) Uani 1 1 d . . .
H42 H -0.4402 -0.1758 0.8407 0.028 Uiso 1 1 calc R . .
C43 C -0.30628(16) -0.12180(16) 0.75046(12) 0.0225(4) Uani 1 1 d . . .
H43 H -0.3315 -0.1365 0.7100 0.027 Uiso 1 1 calc R . .
C44 C -0.20507(15) -0.07709(14) 0.73498(11) 0.0156(4) Uani 1 1 d . . .
C45 C -0.11964(15) -0.04502(14) 0.65954(11) 0.0146(4) Uani 1 1 d . . .
C46 C 0.05892(14) 0.04992(13) 0.62284(10) 0.0122(3) Uani 1 1 d . . .
C47 C 0.15587(14) 0.00832(13) 0.58439(10) 0.0114(3) Uani 1 1 d . . .
C48 C 0.23357(14) 0.09890(13) 0.54235(10) 0.0123(3) Uani 1 1 d . . .
C49 C 0.15633(14) 0.19460(13) 0.55498(10) 0.0123(3) Uani 1 1 d . . .
C50 C 0.05796(14) 0.16543(14) 0.60712(10) 0.0129(4) Uani 1 1 d . . .
C51 C -0.03453(15) 0.23147(14) 0.65103(10) 0.0139(4) Uani 1 1 d . . .
C52 C -0.14458(15) 0.21339(15) 0.65984(11) 0.0174(4) Uani 1 1 d . . .
H52 H -0.1622 0.1588 0.6356 0.021 Uiso 1 1 calc R . .
C53 C -0.22813(16) 0.27523(16) 0.70405(12) 0.0225(4) Uani 1 1 d . . .
H53 H -0.3028 0.2629 0.7097 0.027 Uiso 1 1 calc R . .
C54 C -0.20359(17) 0.35433(16) 0.73980(12) 0.0260(5) Uani 1 1 d . . .
H54 H -0.2612 0.3962 0.7700 0.031 Uiso 1 1 calc R . .
C55 C -0.09507(17) 0.37255(16) 0.73154(12) 0.0246(4) Uani 1 1 d . . .
H55 H -0.0781 0.4272 0.7560 0.029 Uiso 1 1 calc R . .
C56 C -0.01139(16) 0.31166(15) 0.68790(11) 0.0188(4) Uani 1 1 d . . .
H56 H 0.0629 0.3244 0.6828 0.023 Uiso 1 1 calc R . .
C57 C 0.19123(15) 0.29696(14) 0.51244(10) 0.0137(4) Uani 1 1 d . . .
C58 C 0.11482(16) 0.36525(15) 0.49253(12) 0.0212(4) Uani 1 1 d . . .
H58 H 0.0393 0.3463 0.5092 0.025 Uiso 1 1 calc R . .
C59 C 0.14783(18) 0.46015(16) 0.44890(12) 0.0266(5) Uani 1 1 d . . .
H59 H 0.0949 0.5054 0.4359 0.032 Uiso 1 1 calc R . .
C60 C 0.25744(17) 0.48946(15) 0.42414(11) 0.0222(4) Uani 1 1 d . . .
H60 H 0.2799 0.5544 0.3942 0.027 Uiso 1 1 calc R . .
C61 C 0.33372(16) 0.42316(15) 0.44343(11) 0.0199(4) Uani 1 1 d . . .
H61 H 0.4089 0.4431 0.4272 0.024 Uiso 1 1 calc R . .
C62 C 0.30160(15) 0.32797(14) 0.48618(11) 0.0168(4) Uani 1 1 d . . .
H62 H 0.3555 0.2827 0.4980 0.020 Uiso 1 1 calc R . .
C63 C 0.31804(15) 0.10846(13) 0.58404(10) 0.0127(3) Uani 1 1 d . . .
C64 C 0.28155(16) 0.12499(14) 0.66227(11) 0.0169(4) Uani 1 1 d . . .
H64 H 0.2047 0.1256 0.6906 0.020 Uiso 1 1 calc R . .
C65 C 0.35649(17) 0.14039(15) 0.69868(12) 0.0209(4) Uani 1 1 d . . .
H65 H 0.3309 0.1521 0.7518 0.025 Uiso 1 1 calc R . .
C66 C 0.46857(17) 0.13881(15) 0.65819(12) 0.0223(4) Uani 1 1 d . . .
H66 H 0.5199 0.1501 0.6833 0.027 Uiso 1 1 calc R . .
C67 C 0.50595(16) 0.12066(14) 0.58064(12) 0.0196(4) Uani 1 1 d . . .
H67 H 0.5829 0.1185 0.5528 0.024 Uiso 1 1 calc R . .
C68 C 0.43074(15) 0.10567(14) 0.54369(11) 0.0155(4) Uani 1 1 d . . .
H68 H 0.4565 0.0935 0.4906 0.019 Uiso 1 1 calc R . .
C69 C 0.18936(14) -0.10211(13) 0.57802(10) 0.0127(3) Uani 1 1 d . . .
C70 C 0.14902(16) -0.16066(15) 0.53469(11) 0.0179(4) Uani 1 1 d . . .
H70 H 0.0966 -0.1305 0.5123 0.021 Uiso 1 1 calc R . .
C71 C 0.18469(17) -0.26284(15) 0.52390(11) 0.0216(4) Uani 1 1 d . . .
H71 H 0.1575 -0.3019 0.4936 0.026 Uiso 1 1 calc R . .
C72 C 0.25973(16) -0.30801(15) 0.55725(12) 0.0212(4) Uani 1 1 d . . .
H72 H 0.2844 -0.3778 0.5496 0.025 Uiso 1 1 calc R . .
C73 C 0.29852(18) -0.25128(16) 0.60157(13) 0.0267(5) Uani 1 1 d . . .
H73 H 0.3489 -0.2826 0.6253 0.032 Uiso 1 1 calc R . .
C74 C 0.26444(17) -0.14875(15) 0.61169(12) 0.0228(4) Uani 1 1 d . . .
H74 H 0.2924 -0.1100 0.6417 0.027 Uiso 1 1 calc R . .


_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
O1X C2X 1.203(4) . ?
O2X C2X 1.355(5) . ?
O2X C3X 1.428(5) . ?
C1X C2X 1.501(6) . ?
C3X C4X 1.514(5) . ?
O1 C1 1.204(2) . ?
O2 C8 1.207(2) . ?
O3 C11 1.423(2) . ?
O4 C38 1.204(2) . ?
O5 C45 1.212(2) . ?
O6 C48 1.418(2) . ?
N1 C8 1.399(2) . ?
N1 C1 1.414(2) . ?
N1 C9 1.419(2) . ?
N2 C45 1.390(2) . ?
N2 C38 1.408(2) . ?
N2 C46 1.427(2) . ?
C1 C2 1.478(3) . ?
C2 C7 1.381(3) . ?
C2 C3 1.389(3) . ?
C3 C4 1.383(4) . ?
C4 C5 1.379(4) . ?
C5 C6 1.388(4) . ?
C6 C7 1.383(3) . ?
C7 C8 1.489(3) . ?
C9 C10 1.338(3) . ?
C9 C13 1.481(3) . ?
C10 C32 1.470(3) . ?
C10 C11 1.531(2) . ?
C11 C26 1.527(2) . ?
C11 C12 1.535(3) . ?
C12 C13 1.350(3) . ?
C12 C20 1.469(3) . ?
C13 C14 1.480(3) . ?
C14 C19 1.389(3) . ?
C14 C15 1.396(3) . ?
C15 C16 1.388(3) . ?
C16 C17 1.376(4) . ?
C17 C18 1.389(4) . ?
C18 C19 1.386(3) . ?
C20 C21 1.401(3) . ?
C20 C25 1.405(3) . ?
C21 C22 1.385(3) . ?
C22 C23 1.385(3) . ?
C23 C24 1.379(3) . ?
C24 C25 1.392(3) . ?
C26 C31 1.379(3) . ?
C26 C27 1.391(3) . ?
C27 C28 1.384(3) . ?
C28 C29 1.375(3) . ?
C29 C30 1.381(3) . ?
C30 C31 1.389(3) . ?
C32 C33 1.397(3) . ?
C32 C37 1.398(3) . ?
C33 C34 1.388(3) . ?
C34 C35 1.395(4) . ?
C35 C36 1.371(4) . ?
C36 C37 1.387(3) . ?
C38 C39 1.487(3) . ?
C39 C40 1.382(3) . ?
C39 C44 1.390(3) . ?
C40 C41 1.388(3) . ?
C41 C42 1.383(3) . ?
C42 C43 1.393(3) . ?
C43 C44 1.377(3) . ?
C44 C45 1.481(3) . ?
C46 C47 1.331(2) . ?
C46 C50 1.486(2) . ?
C47 C69 1.475(2) . ?
C47 C48 1.534(2) . ?
C48 C49 1.535(2) . ?
C48 C63 1.546(2) . ?
C49 C50 1.345(2) . ?
C49 C57 1.465(2) . ?
C50 C51 1.485(2) . ?
C51 C56 1.396(3) . ?
C51 C52 1.398(3) . ?
C52 C53 1.389(3) . ?
C53 C54 1.379(3) . ?
C54 C55 1.382(3) . ?
C55 C56 1.378(3) . ?
C57 C62 1.400(3) . ?
C57 C58 1.402(3) . ?
C58 C59 1.387(3) . ?
C59 C60 1.385(3) . ?
C60 C61 1.381(3) . ?
C61 C62 1.382(3) . ?
C63 C68 1.389(3) . ?
C63 C64 1.396(2) . ?
C64 C65 1.381(3) . ?
C65 C66 1.382(3) . ?
C66 C67 1.390(3) . ?
C67 C68 1.390(3) . ?
C69 C70 1.391(2) . ?
C69 C74 1.395(3) . ?
C70 C71 1.389(3) . ?
C71 C72 1.384(3) . ?
C72 C73 1.379(3) . ?
C73 C74 1.386(3) . ?

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
C2X O2X C3X 115.4(3) . . ?
O1X C2X O2X 123.0(5) . . ?
O1X C2X C1X 125.7(4) . . ?
O2X C2X C1X 111.3(3) . . ?
O2X C3X C4X 107.9(4) . . ?
C8 N1 C1 111.48(16) . . ?
C8 N1 C9 123.40(16) . . ?
C1 N1 C9 123.71(16) . . ?
C45 N2 C38 111.83(15) . . ?
C45 N2 C46 125.60(15) . . ?
C38 N2 C46 121.25(14) . . ?
O1 C1 N1 124.38(19) . . ?
O1 C1 C2 130.23(19) . . ?
N1 C1 C2 105.39(17) . . ?
C7 C2 C3 121.5(2) . . ?
C7 C2 C1 108.97(18) . . ?
C3 C2 C1 129.5(2) . . ?
C4 C3 C2 116.9(3) . . ?
C5 C4 C3 121.4(2) . . ?
C4 C5 C6 121.9(2) . . ?
C7 C6 C5 116.6(2) . . ?
C2 C7 C6 121.7(2) . . ?
C2 C7 C8 108.15(17) . . ?
C6 C7 C8 130.1(2) . . ?
O2 C8 N1 124.45(18) . . ?
O2 C8 C7 129.77(18) . . ?
N1 C8 C7 105.78(17) . . ?
C10 C9 N1 126.66(17) . . ?
C10 C9 C13 112.07(17) . . ?
N1 C9 C13 121.27(16) . . ?
C9 C10 C32 130.07(17) . . ?
C9 C10 C11 107.14(16) . . ?
C32 C10 C11 122.67(16) . . ?
O3 C11 C26 109.49(15) . . ?
O3 C11 C10 111.66(14) . . ?
C26 C11 C10 108.77(14) . . ?
O3 C11 C12 113.05(15) . . ?
C26 C11 C12 110.05(14) . . ?
C10 C11 C12 103.64(15) . . ?
C13 C12 C20 130.06(18) . . ?
C13 C12 C11 108.74(16) . . ?
C20 C12 C11 120.96(16) . . ?
C12 C13 C14 129.65(18) . . ?
C12 C13 C9 108.37(16) . . ?
C14 C13 C9 121.97(17) . . ?
C19 C14 C15 119.10(19) . . ?
C19 C14 C13 120.85(18) . . ?
C15 C14 C13 120.04(18) . . ?
C16 C15 C14 120.5(2) . . ?
C17 C16 C15 119.9(2) . . ?
C16 C17 C18 120.2(2) . . ?
C19 C18 C17 120.1(2) . . ?
C18 C19 C14 120.2(2) . . ?
C21 C20 C25 117.44(18) . . ?
C21 C20 C12 121.94(18) . . ?
C25 C20 C12 120.58(17) . . ?
C22 C21 C20 121.0(2) . . ?
C21 C22 C23 120.8(2) . . ?
C24 C23 C22 119.14(19) . . ?
C23 C24 C25 120.6(2) . . ?
C24 C25 C20 120.92(19) . . ?
C31 C26 C27 118.95(17) . . ?
C31 C26 C11 122.07(17) . . ?
C27 C26 C11 118.98(17) . . ?
C28 C27 C26 120.33(19) . . ?
C29 C28 C27 120.5(2) . . ?
C28 C29 C30 119.47(18) . . ?
C29 C30 C31 120.28(19) . . ?
C26 C31 C30 120.43(19) . . ?
C33 C32 C37 118.29(19) . . ?
C33 C32 C10 120.45(19) . . ?
C37 C32 C10 121.24(18) . . ?
C34 C33 C32 120.8(2) . . ?
C33 C34 C35 120.0(2) . . ?
C36 C35 C34 119.4(2) . . ?
C35 C36 C37 121.0(2) . . ?
C36 C37 C32 120.4(2) . . ?
O4 C38 N2 124.18(17) . . ?
O4 C38 C39 130.10(18) . . ?
N2 C38 C39 105.71(15) . . ?
C40 C39 C44 121.00(18) . . ?
C40 C39 C38 131.21(18) . . ?
C44 C39 C38 107.79(16) . . ?
C39 C40 C41 117.60(19) . . ?
C42 C41 C40 121.19(19) . . ?
C41 C42 C43 121.29(19) . . ?
C44 C43 C42 117.20(19) . . ?
C43 C44 C39 121.71(18) . . ?
C43 C44 C45 129.66(17) . . ?
C39 C44 C45 108.63(16) . . ?
O5 C45 N2 124.79(17) . . ?
O5 C45 C44 129.23(17) . . ?
N2 C45 C44 105.98(15) . . ?
C47 C46 N2 126.03(16) . . ?
C47 C46 C50 112.00(15) . . ?
N2 C46 C50 121.87(15) . . ?
C46 C47 C69 129.84(16) . . ?
C46 C47 C48 107.12(15) . . ?
C69 C47 C48 123.02(15) . . ?
O6 C48 C47 113.25(13) . . ?
O6 C48 C49 114.20(14) . . ?
C47 C48 C49 103.13(14) . . ?
O6 C48 C63 108.61(14) . . ?
C47 C48 C63 108.94(14) . . ?
C49 C48 C63 108.47(13) . . ?
C50 C49 C57 129.38(16) . . ?
C50 C49 C48 108.67(15) . . ?
C57 C49 C48 121.92(15) . . ?
C49 C50 C51 129.05(16) . . ?
C49 C50 C46 108.10(15) . . ?
C51 C50 C46 122.49(16) . . ?
C56 C51 C52 118.66(17) . . ?
C56 C51 C50 118.81(16) . . ?
C52 C51 C50 122.47(16) . . ?
C53 C52 C51 119.97(18) . . ?
C54 C53 C52 120.52(19) . . ?
C53 C54 C55 119.89(18) . . ?
C56 C55 C54 120.17(19) . . ?
C55 C56 C51 120.80(18) . . ?
C62 C57 C58 117.46(17) . . ?
C62 C57 C49 122.07(16) . . ?
C58 C57 C49 120.36(17) . . ?
C59 C58 C57 120.96(18) . . ?
C60 C59 C58 120.48(18) . . ?
C61 C60 C59 119.28(18) . . ?
C60 C61 C62 120.54(18) . . ?
C61 C62 C57 121.27(17) . . ?
C68 C63 C64 119.12(16) . . ?
C68 C63 C48 120.74(16) . . ?
C64 C63 C48 120.07(15) . . ?
C65 C64 C63 120.43(18) . . ?
C64 C65 C66 120.35(18) . . ?
C65 C66 C67 119.75(18) . . ?
C66 C67 C68 120.06(18) . . ?
C63 C68 C67 120.28(18) . . ?
C70 C69 C74 118.72(17) . . ?
C70 C69 C47 119.51(16) . . ?
C74 C69 C47 121.72(16) . . ?
C71 C70 C69 120.52(17) . . ?
C72 C71 C70 120.17(18) . . ?
C73 C72 C71 119.73(18) . . ?
C72 C73 C74 120.40(18) . . ?
C73 C74 C69 120.43(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3O O2 0.858(10) 1.963(11) 2.8107(19) 170(3) 2_667

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.063


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d135
_database_code_depnum_ccdc_archive 'CCDC 925572'
_audit_update_record             
;
2013-02-20 deposited with the CCDC.
2016-03-07 downloaded from the CCDC.
;
#TrackingRef 'web_deposit_cif_file_0_JianWang_1361330620.D135.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C41 H34 O6'
_chemical_formula_weight         622.68

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.5936(12)
_cell_length_b                   9.4163(12)
_cell_length_c                   34.688(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.150(3)
_cell_angle_gamma                90.00
_cell_volume                     3128.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    981
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      25.43

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6642
_exptl_absorpt_correction_T_max  0.7899
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21758
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         1.18
_diffrn_reflns_theta_max         27.49
_reflns_number_total             7194
_reflns_number_gt                5449
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0808P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7194
_refine_ls_number_parameters     434
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1367
_refine_ls_wR_factor_gt          0.1235
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_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
O1 O 0.07389(11) 0.60366(12) 0.14612(3) 0.0227(3) Uani 1 1 d . . .
O2 O 0.28311(11) 0.70804(11) 0.13990(3) 0.0180(2) Uani 1 1 d . . .
O3 O 0.50396(11) 1.01452(11) 0.07135(3) 0.0178(2) Uani 1 1 d . . .
H3O H 0.471(2) 1.066(2) 0.0908(6) 0.035(6) Uiso 1 1 d . . .
O4 O 0.46216(11) 0.89944(12) 0.18519(3) 0.0178(2) Uani 1 1 d . . .
H4O H 0.429(2) 0.972(2) 0.1711(6) 0.037(6) Uiso 1 1 d . . .
C1 C 0.15714(16) 0.65374(16) 0.12532(5) 0.0180(3) Uani 1 1 d . . .
C2 C 0.15184(16) 0.67524(16) 0.08322(5) 0.0172(3) Uani 1 1 d . . .
C3 C 0.04699(16) 0.63885(17) 0.05593(5) 0.0203(3) Uani 1 1 d . . .
H3A H -0.0337 0.5886 0.0629 0.024 Uiso 1 1 calc R . .
C4 C 0.06495(17) 0.67895(17) 0.01810(5) 0.0221(4) Uani 1 1 d . . .
H4A H -0.0045 0.6556 -0.0014 0.026 Uiso 1 1 calc R . .
C5 C 0.18366(17) 0.75309(17) 0.00839(5) 0.0199(3) Uani 1 1 d . . .
H5 H 0.1931 0.7801 -0.0177 0.024 Uiso 1 1 calc R . .
C6 C 0.28845(16) 0.78842(16) 0.03585(4) 0.0182(3) Uani 1 1 d . . .
H6 H 0.3690 0.8389 0.0289 0.022 Uiso 1 1 calc R . .
C7 C 0.27186(15) 0.74750(15) 0.07403(5) 0.0161(3) Uani 1 1 d . . .
C8 C 0.35846(16) 0.76627(16) 0.10987(4) 0.0155(3) Uani 1 1 d . . .
C9 C 0.48475(15) 0.82166(15) 0.11829(4) 0.0142(3) Uani 1 1 d . . .
C10 C 0.57553(16) 0.89603(15) 0.08942(4) 0.0143(3) Uani 1 1 d . . .
C11 C 0.69695(15) 0.95120(15) 0.11601(4) 0.0147(3) Uani 1 1 d . . .
C12 C 0.68210(15) 0.91988(15) 0.15311(4) 0.0145(3) Uani 1 1 d . . .
C13 C 0.55189(15) 0.83142(15) 0.15917(4) 0.0143(3) Uani 1 1 d . . .
C14 C 0.62109(15) 0.79996(16) 0.05710(4) 0.0153(3) Uani 1 1 d . . .
C15 C 0.63724(16) 0.65440(16) 0.06279(5) 0.0170(3) Uani 1 1 d . . .
H15 H 0.6244 0.6149 0.0875 0.020 Uiso 1 1 calc R . .
C16 C 0.67194(17) 0.56636(17) 0.03266(5) 0.0204(3) Uani 1 1 d . . .
H16 H 0.6826 0.4672 0.0369 0.024 Uiso 1 1 calc R . .
C17 C 0.69114(16) 0.62275(18) -0.00363(5) 0.0215(4) Uani 1 1 d . . .
H17 H 0.7137 0.5624 -0.0243 0.026 Uiso 1 1 calc R . .
C18 C 0.67725(16) 0.76750(18) -0.00944(5) 0.0213(4) Uani 1 1 d . . .
H18 H 0.6908 0.8067 -0.0342 0.026 Uiso 1 1 calc R . .
C19 C 0.64358(16) 0.85592(17) 0.02074(5) 0.0190(3) Uani 1 1 d . . .
H19 H 0.6358 0.9554 0.0166 0.023 Uiso 1 1 calc R . .
C20 C 0.80931(16) 1.04258(16) 0.10164(4) 0.0160(3) Uani 1 1 d . . .
C21 C 0.91131(17) 0.98931(17) 0.07840(5) 0.0212(4) Uani 1 1 d . . .
H21 H 0.9057 0.8936 0.0698 0.025 Uiso 1 1 calc R . .
C22 C 1.02098(17) 1.07434(18) 0.06761(5) 0.0241(4) Uani 1 1 d . . .
H22 H 1.0906 1.0365 0.0521 0.029 Uiso 1 1 calc R . .
C23 C 1.02829(17) 1.21471(18) 0.07961(5) 0.0222(4) Uani 1 1 d . . .
H23 H 1.1032 1.2731 0.0723 0.027 Uiso 1 1 calc R . .
C24 C 0.92718(18) 1.26999(18) 0.10210(5) 0.0222(4) Uani 1 1 d . . .
H24 H 0.9319 1.3665 0.1101 0.027 Uiso 1 1 calc R . .
C25 C 0.81805(17) 1.18388(17) 0.11307(4) 0.0194(3) Uani 1 1 d . . .
H25 H 0.7487 1.2223 0.1286 0.023 Uiso 1 1 calc R . .
C26 C 0.78000(16) 0.95684(15) 0.18628(4) 0.0157(3) Uani 1 1 d . . .
C27 C 0.91686(17) 0.90560(17) 0.18791(5) 0.0224(4) Uani 1 1 d . . .
H27 H 0.9481 0.8497 0.1673 0.027 Uiso 1 1 calc R . .
C28 C 1.00743(18) 0.93565(18) 0.21938(5) 0.0267(4) Uani 1 1 d . . .
H28 H 1.1000 0.8994 0.2203 0.032 Uiso 1 1 calc R . .
C29 C 0.96338(18) 1.01834(18) 0.24938(5) 0.0256(4) Uani 1 1 d . . .
H29 H 1.0258 1.0396 0.2708 0.031 Uiso 1 1 calc R . .
C30 C 0.82850(18) 1.06985(18) 0.24802(5) 0.0232(4) Uani 1 1 d . . .
H30 H 0.7982 1.1267 0.2686 0.028 Uiso 1 1 calc R . .
C31 C 0.73694(17) 1.03908(16) 0.21676(5) 0.0184(3) Uani 1 1 d . . .
H31 H 0.6441 1.0745 0.2162 0.022 Uiso 1 1 calc R . .
C32 C 0.59175(16) 0.68609(15) 0.17601(4) 0.0149(3) Uani 1 1 d . . .
C33 C 0.51084(17) 0.61958(17) 0.20276(5) 0.0193(3) Uani 1 1 d . . .
H33 H 0.4291 0.6649 0.2109 0.023 Uiso 1 1 calc R . .
C34 C 0.54882(19) 0.48782(17) 0.21752(5) 0.0241(4) Uani 1 1 d . . .
H34 H 0.4932 0.4435 0.2359 0.029 Uiso 1 1 calc R . .
C35 C 0.66692(19) 0.42017(17) 0.20575(5) 0.0244(4) Uani 1 1 d . . .
H35 H 0.6922 0.3295 0.2159 0.029 Uiso 1 1 calc R . .
C36 C 0.74856(17) 0.48505(17) 0.17906(5) 0.0206(3) Uani 1 1 d . . .
H36 H 0.8297 0.4388 0.1708 0.025 Uiso 1 1 calc R . .
C37 C 0.71136(16) 0.61762(16) 0.16447(4) 0.0160(3) Uani 1 1 d . . .
H37 H 0.7680 0.6623 0.1464 0.019 Uiso 1 1 calc R . .
O1S O 0.38884(13) 0.14592(12) 0.13531(4) 0.0278(3) Uani 1 1 d . . .
O2S O 0.26303(13) 0.32982(12) 0.15471(3) 0.0262(3) Uani 1 1 d . . .
C1S C 0.4353(2) 0.37958(18) 0.11173(5) 0.0275(4) Uani 1 1 d . . .
H1S1 H 0.4924 0.4406 0.1292 0.041 Uiso 1 1 calc R . .
H1S2 H 0.3669 0.4378 0.0969 0.041 Uiso 1 1 calc R . .
H1S3 H 0.4955 0.3308 0.0940 0.041 Uiso 1 1 calc R . .
C2S C 0.36078(17) 0.27214(17) 0.13478(5) 0.0203(3) Uani 1 1 d . . .
C3S C 0.18640(19) 0.2371(2) 0.17998(5) 0.0308(4) Uani 1 1 d . . .
H3S1 H 0.1687 0.1445 0.1671 0.037 Uiso 1 1 calc R . .
H3S2 H 0.0951 0.2806 0.1849 0.037 Uiso 1 1 calc R . .
C4S C 0.26780(19) 0.21410(19) 0.21752(5) 0.0281(4) Uani 1 1 d . . .
H4S1 H 0.3571 0.1688 0.2127 0.042 Uiso 1 1 calc R . .
H4S2 H 0.2145 0.1527 0.2341 0.042 Uiso 1 1 calc R . .
H4S3 H 0.2850 0.3057 0.2303 0.042 Uiso 1 1 calc R . .


_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
O1 C1 1.2018(19) . ?
O2 C1 1.3821(19) . ?
O2 C8 1.4109(18) . ?
O3 C10 1.4361(18) . ?
O3 H3O 0.90(2) . ?
O4 C13 1.4323(18) . ?
O4 H4O 0.89(2) . ?
C1 C2 1.473(2) . ?
C2 C3 1.386(2) . ?
C2 C7 1.389(2) . ?
C3 C4 1.385(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.393(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.387(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.397(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.468(2) . ?
C8 C9 1.336(2) . ?
C9 C13 1.528(2) . ?
C9 C10 1.532(2) . ?
C10 C14 1.523(2) . ?
C10 C11 1.536(2) . ?
C11 C12 1.335(2) . ?
C11 C20 1.487(2) . ?
C12 C26 1.486(2) . ?
C12 C13 1.526(2) . ?
C13 C32 1.528(2) . ?
C14 C15 1.392(2) . ?
C14 C19 1.394(2) . ?
C15 C16 1.389(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.390(2) . ?
C20 C21 1.395(2) . ?
C21 C22 1.390(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.394(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C31 1.391(2) . ?
C26 C27 1.397(2) . ?
C27 C28 1.386(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.384(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.380(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.388(2) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C33 1.391(2) . ?
C32 C37 1.394(2) . ?
C33 C34 1.383(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.381(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.387(2) . ?
C35 H35 0.9500 . ?
C36 C37 1.386(2) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
O1S C2S 1.2186(19) . ?
O2S C2S 1.3128(19) . ?
O2S C3S 1.464(2) . ?
C1S C2S 1.496(2) . ?
C1S H1S1 0.9800 . ?
C1S H1S2 0.9800 . ?
C1S H1S3 0.9800 . ?
C3S C4S 1.497(3) . ?
C3S H3S1 0.9900 . ?
C3S H3S2 0.9900 . ?
C4S H4S1 0.9800 . ?
C4S H4S2 0.9800 . ?
C4S H4S3 0.9800 . ?

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
C1 O2 C8 110.30(12) . . ?
C10 O3 H3O 105.4(13) . . ?
C13 O4 H4O 101.9(14) . . ?
O1 C1 O2 121.48(15) . . ?
O1 C1 C2 131.41(15) . . ?
O2 C1 C2 107.09(13) . . ?
C3 C2 C7 122.96(15) . . ?
C3 C2 C1 128.87(14) . . ?
C7 C2 C1 108.11(14) . . ?
C4 C3 C2 117.14(15) . . ?
C4 C3 H3A 121.4 . . ?
C2 C3 H3A 121.4 . . ?
C3 C4 C5 120.77(15) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C6 C5 C4 121.70(15) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 117.98(15) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 H6 121.0 . . ?
C2 C7 C6 119.45(14) . . ?
C2 C7 C8 107.60(14) . . ?
C6 C7 C8 132.95(14) . . ?
C9 C8 O2 119.04(13) . . ?
C9 C8 C7 134.13(14) . . ?
O2 C8 C7 106.82(12) . . ?
C8 C9 C13 123.87(14) . . ?
C8 C9 C10 125.21(14) . . ?
C13 C9 C10 110.69(12) . . ?
O3 C10 C14 106.83(12) . . ?
O3 C10 C9 111.42(12) . . ?
C14 C10 C9 113.96(12) . . ?
O3 C10 C11 109.15(12) . . ?
C14 C10 C11 113.83(12) . . ?
C9 C10 C11 101.64(12) . . ?
C12 C11 C20 124.66(14) . . ?
C12 C11 C10 112.73(13) . . ?
C20 C11 C10 122.30(13) . . ?
C11 C12 C26 126.73(14) . . ?
C11 C12 C13 112.64(13) . . ?
C26 C12 C13 120.57(13) . . ?
O4 C13 C12 111.58(11) . . ?
O4 C13 C9 112.00(12) . . ?
C12 C13 C9 102.22(12) . . ?
O4 C13 C32 107.81(12) . . ?
C12 C13 C32 110.61(12) . . ?
C9 C13 C32 112.63(12) . . ?
C15 C14 C19 118.60(14) . . ?
C15 C14 C10 120.95(13) . . ?
C19 C14 C10 120.42(14) . . ?
C16 C15 C14 120.68(15) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 120.24(15) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 119.51(15) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.35(15) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 120.59(15) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C25 C20 C21 118.42(14) . . ?
C25 C20 C11 119.47(13) . . ?
C21 C20 C11 122.02(14) . . ?
C22 C21 C20 120.93(15) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C23 C22 C21 119.66(15) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C24 C23 C22 120.27(15) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.80(15) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C20 C25 C24 120.90(15) . . ?
C20 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C31 C26 C27 118.63(15) . . ?
C31 C26 C12 121.15(14) . . ?
C27 C26 C12 120.20(14) . . ?
C28 C27 C26 120.55(16) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C29 C28 C27 120.17(16) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C30 C29 C28 119.76(16) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C29 C30 C31 120.34(16) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
C30 C31 C26 120.54(15) . . ?
C30 C31 H31 119.7 . . ?
C26 C31 H31 119.7 . . ?
C33 C32 C37 118.79(14) . . ?
C33 C32 C13 121.40(13) . . ?
C37 C32 C13 119.80(13) . . ?
C34 C33 C32 120.36(15) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C35 C34 C33 120.53(15) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C34 C35 C36 119.78(15) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
C37 C36 C35 119.80(15) . . ?
C37 C36 H36 120.1 . . ?
C35 C36 H36 120.1 . . ?
C36 C37 C32 120.73(14) . . ?
C36 C37 H37 119.6 . . ?
C32 C37 H37 119.6 . . ?
C2S O2S C3S 117.73(13) . . ?
C2S C1S H1S1 109.5 . . ?
C2S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
C2S C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
O1S C2S O2S 124.01(15) . . ?
O1S C2S C1S 123.78(15) . . ?
O2S C2S C1S 112.21(14) . . ?
O2S C3S C4S 110.61(14) . . ?
O2S C3S H3S1 109.5 . . ?
C4S C3S H3S1 109.5 . . ?
O2S C3S H3S2 109.5 . . ?
C4S C3S H3S2 109.5 . . ?
H3S1 C3S H3S2 108.1 . . ?
C3S C4S H4S1 109.5 . . ?
C3S C4S H4S2 109.5 . . ?
H4S1 C4S H4S2 109.5 . . ?
C3S C4S H4S3 109.5 . . ?
H4S1 C4S H4S3 109.5 . . ?
H4S2 C4S H4S3 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4O O1S 0.89(2) 2.08(2) 2.9566(17) 169.4(19) 1_565
O3 H3O O1S 0.90(2) 1.93(2) 2.8182(17) 170.5(19) 1_565

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.071


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d009t5
_database_code_depnum_ccdc_archive 'CCDC 975849'
_audit_update_record             
;
2013-12-08 deposited with the CCDC.
2016-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H26 O2'
_chemical_formula_weight         514.59

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                   9.837(2)
_cell_length_b                   10.766(2)
_cell_length_c                   13.710(3)
_cell_angle_alpha                87.68(3)
_cell_angle_beta                 77.40(3)
_cell_angle_gamma                71.54(3)
_cell_volume                     1343.5(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3000
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      24.90

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             540
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6404
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'TWINABS v2008/4 ,Sheldrick'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6168
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0508
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         27.50
_reflns_number_total             6168
_reflns_number_gt                4807
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0929P)²+0.0000P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6168
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1527
_refine_ls_wR_factor_gt          0.1418
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_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
O1 O 0.83929(14) 0.83835(12) 0.58364(9) 0.0211(3) Uani 1 1 d . . .
O2 O 1.06283(15) 0.76141(13) 0.48205(11) 0.0287(3) Uani 1 1 d . . .
C1 C 0.9448(2) 0.84327(18) 0.49960(14) 0.0214(4) Uani 1 1 d . . .
C2 C 0.8789(2) 0.95926(18) 0.44633(14) 0.0202(4) Uani 1 1 d . . .
C3 C 0.9413(2) 1.00533(19) 0.35700(13) 0.0228(4) Uani 1 1 d . . .
H3 H 1.0391 0.9614 0.3228 0.027 Uiso 1 1 calc R . .
C4 C 0.8557(2) 1.1178(2) 0.31957(13) 0.0250(4) Uani 1 1 d . . .
C5 C 0.7076(2) 1.17180(19) 0.36769(14) 0.0248(4) Uani 1 1 d . . .
H5 H 0.6474 1.2439 0.3384 0.030 Uiso 1 1 calc R . .
C6 C 0.6452(2) 1.12493(18) 0.45591(13) 0.0212(4) Uani 1 1 d . . .
H6 H 0.5444 1.1631 0.4865 0.025 Uiso 1 1 calc R . .
C7 C 0.7355(2) 1.01971(18) 0.49830(13) 0.0197(4) Uani 1 1 d . . .
C8 C 0.7123(2) 0.94545(17) 0.58910(13) 0.0176(4) Uani 1 1 d . . .
C9 C 0.9206(3) 1.1820(2) 0.23039(15) 0.0342(5) Uani 1 1 d . . .
H9A H 0.9494 1.2533 0.2528 0.051 Uiso 1 1 calc R . .
H9B H 0.8476 1.2173 0.1894 0.051 Uiso 1 1 calc R . .
H9C H 1.0071 1.1172 0.1906 0.051 Uiso 1 1 calc R . .
C10 C 0.6025(2) 0.95871(17) 0.67206(13) 0.0177(4) Uani 1 1 d . . .
C11 C 0.4744(2) 1.07385(17) 0.70968(13) 0.0172(4) Uani 1 1 d . . .
C12 C 0.40019(19) 1.04317(17) 0.79778(13) 0.0165(4) Uani 1 1 d . . .
C13 C 0.4744(2) 0.90613(17) 0.82047(13) 0.0169(4) Uani 1 1 d . . .
C14 C 0.5956(2) 0.85586(17) 0.74605(13) 0.0173(4) Uani 1 1 d . . .
C15 C 0.4325(2) 1.20704(16) 0.66810(12) 0.0164(4) Uani 1 1 d . . .
C16 C 0.5218(2) 1.28687(18) 0.65977(14) 0.0219(4) Uani 1 1 d . . .
H16 H 0.6150 1.2543 0.6769 0.026 Uiso 1 1 calc R . .
C17 C 0.4751(2) 1.41306(19) 0.62677(14) 0.0270(5) Uani 1 1 d . . .
H17 H 0.5362 1.4670 0.6218 0.032 Uiso 1 1 calc R . .
C18 C 0.3396(2) 1.46182(19) 0.60074(15) 0.0276(5) Uani 1 1 d . . .
H18 H 0.3085 1.5485 0.5777 0.033 Uiso 1 1 calc R . .
C19 C 0.2500(2) 1.38375(18) 0.60842(14) 0.0228(4) Uani 1 1 d . . .
H19 H 0.1572 1.4166 0.5907 0.027 Uiso 1 1 calc R . .
C20 C 0.2964(2) 1.25717(18) 0.64220(13) 0.0191(4) Uani 1 1 d . . .
H20 H 0.2346 1.2039 0.6478 0.023 Uiso 1 1 calc R . .
C21 C 0.2664(2) 1.13086(17) 0.86254(12) 0.0167(4) Uani 1 1 d . . .
C22 C 0.2611(2) 1.25396(17) 0.89417(13) 0.0190(4) Uani 1 1 d . . .
H22 H 0.3443 1.2830 0.8733 0.023 Uiso 1 1 calc R . .
C23 C 0.1355(2) 1.33423(18) 0.95580(14) 0.0223(4) Uani 1 1 d . . .
H23 H 0.1331 1.4180 0.9770 0.027 Uiso 1 1 calc R . .
C24 C 0.0135(2) 1.29346(18) 0.98674(14) 0.0236(4) Uani 1 1 d . . .
H24 H -0.0723 1.3489 1.0292 0.028 Uiso 1 1 calc R . .
C25 C 0.0165(2) 1.17149(18) 0.95570(14) 0.0224(4) Uani 1 1 d . . .
H25 H -0.0674 1.1434 0.9765 0.027 Uiso 1 1 calc R . .
C26 C 0.1422(2) 1.09067(18) 0.89434(13) 0.0197(4) Uani 1 1 d . . .
H26 H 0.1441 1.0069 0.8736 0.024 Uiso 1 1 calc R . .
C27 C 0.4239(2) 0.83933(18) 0.91087(14) 0.0191(4) Uani 1 1 d . . .
C28 C 0.3835(2) 0.9016(2) 1.00473(14) 0.0225(4) Uani 1 1 d . . .
H28 H 0.3833 0.9893 1.0100 0.027 Uiso 1 1 calc R . .
C29 C 0.3434(2) 0.8375(2) 1.09067(15) 0.0294(5) Uani 1 1 d . . .
H29 H 0.3183 0.8805 1.1543 0.035 Uiso 1 1 calc R . .
C30 C 0.3402(2) 0.7106(2) 1.08356(17) 0.0339(5) Uani 1 1 d . . .
H30 H 0.3139 0.6660 1.1423 0.041 Uiso 1 1 calc R . .
C31 C 0.3751(2) 0.6493(2) 0.99126(17) 0.0317(5) Uani 1 1 d . . .
H31 H 0.3699 0.5632 0.9865 0.038 Uiso 1 1 calc R . .
C32 C 0.4180(2) 0.71176(18) 0.90475(16) 0.0247(4) Uani 1 1 d . . .
H32 H 0.4433 0.6678 0.8415 0.030 Uiso 1 1 calc R . .
C33 C 0.69488(19) 0.71897(17) 0.73731(13) 0.0175(4) Uani 1 1 d . . .
C34 C 0.7744(2) 0.66798(19) 0.80993(14) 0.0232(4) Uani 1 1 d . . .
H34 H 0.7678 0.7222 0.8649 0.028 Uiso 1 1 calc R . .
C35 C 0.8634(2) 0.5385(2) 0.80262(15) 0.0286(5) Uani 1 1 d . . .
H35 H 0.9178 0.5047 0.8525 0.034 Uiso 1 1 calc R . .
C36 C 0.8737(2) 0.45846(19) 0.72388(16) 0.0277(5) Uani 1 1 d . . .
H36 H 0.9339 0.3695 0.7199 0.033 Uiso 1 1 calc R . .
C37 C 0.7959(2) 0.50797(19) 0.65022(15) 0.0258(4) Uani 1 1 d . . .
H37 H 0.8035 0.4533 0.5953 0.031 Uiso 1 1 calc R . .
C38 C 0.7074(2) 0.63713(18) 0.65709(14) 0.0224(4) Uani 1 1 d . . .
H38 H 0.6542 0.6708 0.6066 0.027 Uiso 1 1 calc R . .


_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
O1 C1 1.384(2) . ?
O1 C8 1.397(2) . ?
O2 C1 1.196(2) . ?
C1 C2 1.460(3) . ?
C2 C7 1.392(3) . ?
C2 C3 1.392(3) . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.404(3) . ?
C4 C9 1.500(3) . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.467(3) . ?
C8 C10 1.364(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.473(3) . ?
C10 C14 1.479(2) . ?
C11 C12 1.355(2) . ?
C11 C15 1.488(2) . ?
C12 C21 1.478(3) . ?
C12 C13 1.479(2) . ?
C13 C14 1.364(3) . ?
C13 C27 1.478(3) . ?
C14 C33 1.481(2) . ?
C15 C20 1.394(3) . ?
C15 C16 1.396(3) . ?
C16 C17 1.381(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.393(2) . ?
C21 C26 1.399(2) . ?
C22 C23 1.384(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.393(3) . ?
C27 C32 1.399(3) . ?
C28 C29 1.387(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.384(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.375(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.391(3) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.389(3) . ?
C33 C38 1.397(3) . ?
C34 C35 1.386(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.375(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.387(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.382(3) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?

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
C1 O1 C8 110.81(14) . . ?
O2 C1 O1 121.29(18) . . ?
O2 C1 C2 132.25(19) . . ?
O1 C1 C2 106.45(16) . . ?
C7 C2 C3 123.03(18) . . ?
C7 C2 C1 108.81(17) . . ?
C3 C2 C1 128.14(17) . . ?
C4 C3 C2 117.75(18) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C4 C5 118.83(17) . . ?
C3 C4 C9 120.74(19) . . ?
C5 C4 C9 120.43(19) . . ?
C6 C5 C4 123.10(19) . . ?
C6 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C5 C6 C7 117.65(18) . . ?
C5 C6 H6 121.2 . . ?
C7 C6 H6 121.2 . . ?
C2 C7 C6 119.14(17) . . ?
C2 C7 C8 106.81(16) . . ?
C6 C7 C8 133.91(18) . . ?
C10 C8 O1 117.33(16) . . ?
C10 C8 C7 135.71(18) . . ?
O1 C8 C7 106.94(15) . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 C11 129.19(17) . . ?
C8 C10 C14 124.54(17) . . ?
C11 C10 C14 106.21(15) . . ?
C12 C11 C10 108.05(16) . . ?
C12 C11 C15 122.70(16) . . ?
C10 C11 C15 129.07(16) . . ?
C11 C12 C21 126.37(16) . . ?
C11 C12 C13 109.25(16) . . ?
C21 C12 C13 124.39(15) . . ?
C14 C13 C27 127.18(16) . . ?
C14 C13 C12 108.57(15) . . ?
C27 C13 C12 124.23(16) . . ?
C13 C14 C10 107.91(16) . . ?
C13 C14 C33 125.60(16) . . ?
C10 C14 C33 126.31(16) . . ?
C20 C15 C16 118.71(16) . . ?
C20 C15 C11 119.32(16) . . ?
C16 C15 C11 121.86(16) . . ?
C17 C16 C15 120.25(18) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.56(18) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 119.86(17) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 119.60(18) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C19 C20 C15 121.02(17) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
C22 C21 C26 118.53(17) . . ?
C22 C21 C12 121.21(16) . . ?
C26 C21 C12 120.25(16) . . ?
C23 C22 C21 120.47(18) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C24 C23 C22 120.47(18) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 119.87(18) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C26 C25 C24 119.83(18) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C21 120.82(17) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
C28 C27 C32 118.39(17) . . ?
C28 C27 C13 120.49(16) . . ?
C32 C27 C13 121.11(17) . . ?
C29 C28 C27 121.06(19) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C30 C29 C28 119.8(2) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C31 C30 C29 119.84(19) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C30 C31 C32 120.76(19) . . ?
C30 C31 H31 119.6 . . ?
C32 C31 H31 119.6 . . ?
C31 C32 C27 120.0(2) . . ?
C31 C32 H32 120.0 . . ?
C27 C32 H32 120.0 . . ?
C34 C33 C38 118.54(17) . . ?
C34 C33 C14 120.84(16) . . ?
C38 C33 C14 120.60(16) . . ?
C35 C34 C33 120.33(18) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C36 C35 C34 120.63(19) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C35 C36 C37 119.83(18) . . ?
C35 C36 H36 120.1 . . ?
C37 C36 H36 120.1 . . ?
C38 C37 C36 119.71(19) . . ?
C38 C37 H37 120.1 . . ?
C36 C37 H37 120.1 . . ?
C37 C38 C33 120.95(18) . . ?
C37 C38 H38 119.5 . . ?
C33 C38 H38 119.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.095
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d170
_database_code_depnum_ccdc_archive 'CCDC 975850'
_audit_update_record             
;
2013-12-08 deposited with the CCDC.
2016-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H20 O'
_chemical_formula_weight         384.45

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           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.128(2)
_cell_length_b                   8.1552(8)
_cell_length_c                   21.487(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.724(2)
_cell_angle_gamma                90.00
_cell_volume                     3976.0(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3664
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6573
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13207
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4559
_reflns_number_gt                3739
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0610P)²+2.9991P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4559
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1312
_refine_ls_wR_factor_gt          0.1243
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
O1 O 0.19939(5) 0.51859(15) 0.39020(6) 0.0217(3) Uani 1 1 d . . .
C1 C 0.21898(6) 0.50387(18) 0.45436(8) 0.0134(3) Uani 1 1 d . . .
C2 C 0.18380(7) 0.50548(18) 0.49233(8) 0.0133(3) Uani 1 1 d . . .
C3 C 0.22315(6) 0.50504(17) 0.56320(8) 0.0121(3) Uani 1 1 d . . .
C4 C 0.28518(6) 0.49123(17) 0.57469(8) 0.0124(3) Uani 1 1 d . . .
C5 C 0.28305(6) 0.48906(17) 0.51051(8) 0.0129(3) Uani 1 1 d . . .
C6 C 0.11900(6) 0.50028(18) 0.45329(8) 0.0133(3) Uani 1 1 d . . .
C7 C 0.08612(7) 0.5780(2) 0.38690(8) 0.0184(3) Uani 1 1 d . . .
H7 H 0.1059 0.6336 0.3660 0.022 Uiso 1 1 calc R . .
C8 C 0.02517(7) 0.5748(2) 0.35140(9) 0.0249(4) Uani 1 1 d . . .
H8 H 0.0035 0.6303 0.3069 0.030 Uiso 1 1 calc R . .
C9 C -0.00453(7) 0.4921(2) 0.37977(9) 0.0261(4) Uani 1 1 d . . .
H9 H -0.0464 0.4911 0.3553 0.031 Uiso 1 1 calc R . .
C10 C 0.02744(7) 0.4102(2) 0.44458(9) 0.0229(4) Uani 1 1 d . . .
H10 H 0.0073 0.3511 0.4641 0.027 Uiso 1 1 calc R . .
C11 C 0.08819(7) 0.41406(18) 0.48073(8) 0.0170(3) Uani 1 1 d . . .
H11 H 0.1095 0.3573 0.5250 0.020 Uiso 1 1 calc R . .
C12 C 0.21015(6) 0.52048(17) 0.62234(8) 0.0117(3) Uani 1 1 d . . .
C13 C 0.16946(6) 0.63714(18) 0.61735(8) 0.0137(3) Uani 1 1 d . . .
H13 H 0.1517 0.7079 0.5769 0.016 Uiso 1 1 calc R . .
C14 C 0.15458(7) 0.65123(19) 0.67082(8) 0.0152(3) Uani 1 1 d . . .
H14 H 0.1270 0.7320 0.6671 0.018 Uiso 1 1 calc R . .
C15 C 0.18003(7) 0.54734(19) 0.72977(8) 0.0167(3) Uani 1 1 d . . .
H15 H 0.1690 0.5548 0.7657 0.020 Uiso 1 1 calc R . .
C16 C 0.22141(7) 0.43297(19) 0.73604(8) 0.0160(3) Uani 1 1 d . . .
H16 H 0.2392 0.3629 0.7767 0.019 Uiso 1 1 calc R . .
C17 C 0.23699(6) 0.42029(18) 0.68315(8) 0.0140(3) Uani 1 1 d . . .
H17 H 0.2661 0.3431 0.6883 0.017 Uiso 1 1 calc R . .
C18 C 0.33814(6) 0.48197(18) 0.64627(8) 0.0130(3) Uani 1 1 d . . .
C19 C 0.35226(7) 0.60783(19) 0.69623(8) 0.0163(3) Uani 1 1 d . . .
H19 H 0.3270 0.7001 0.6847 0.020 Uiso 1 1 calc R . .
C20 C 0.40309(7) 0.5985(2) 0.76257(9) 0.0241(4) Uani 1 1 d . . .
H20 H 0.4129 0.6857 0.7959 0.029 Uiso 1 1 calc R . .
C21 C 0.43967(7) 0.4625(2) 0.78051(9) 0.0269(4) Uani 1 1 d . . .
H21 H 0.4744 0.4562 0.8260 0.032 Uiso 1 1 calc R . .
C22 C 0.42518(7) 0.3361(2) 0.73162(9) 0.0238(4) Uani 1 1 d . . .
H22 H 0.4497 0.2418 0.7440 0.029 Uiso 1 1 calc R . .
C23 C 0.37523(7) 0.34611(19) 0.66480(8) 0.0169(3) Uani 1 1 d . . .
H23 H 0.3661 0.2597 0.6313 0.020 Uiso 1 1 calc R . .
C24 C 0.33008(7) 0.48950(18) 0.49165(8) 0.0140(3) Uani 1 1 d . . .
C25 C 0.38596(7) 0.55380(19) 0.53798(8) 0.0163(3) Uani 1 1 d . . .
H25 H 0.3949 0.5914 0.5842 0.020 Uiso 1 1 calc R . .
C26 C 0.42836(7) 0.5633(2) 0.51734(9) 0.0203(3) Uani 1 1 d . . .
H26 H 0.4659 0.6093 0.5490 0.024 Uiso 1 1 calc R . .
C27 C 0.41633(7) 0.5061(2) 0.45056(9) 0.0208(4) Uani 1 1 d . . .
H27 H 0.4455 0.5124 0.4365 0.025 Uiso 1 1 calc R . .
C28 C 0.36161(7) 0.43985(19) 0.40463(9) 0.0195(3) Uani 1 1 d . . .
H28 H 0.3533 0.3996 0.3591 0.023 Uiso 1 1 calc R . .
C29 C 0.31867(7) 0.43181(18) 0.42472(8) 0.0158(3) Uani 1 1 d . . .
H29 H 0.2811 0.3866 0.3926 0.019 Uiso 1 1 calc R . .


_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
O1 C1 1.2155(18) . ?
C1 C2 1.5014(19) . ?
C1 C5 1.507(2) . ?
C2 C3 1.350(2) . ?
C2 C6 1.471(2) . ?
C3 C12 1.4746(19) . ?
C3 C4 1.518(2) . ?
C4 C5 1.352(2) . ?
C4 C18 1.475(2) . ?
C5 C24 1.472(2) . ?
C6 C7 1.400(2) . ?
C6 C11 1.400(2) . ?
C7 C8 1.384(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.378(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.379(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.391(2) . ?
C12 C17 1.399(2) . ?
C13 C14 1.3880(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.394(2) . ?
C18 C19 1.396(2) . ?
C19 C20 1.387(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C29 1.398(2) . ?
C24 C25 1.399(2) . ?
C25 C26 1.385(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.389(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.382(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.389(2) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?

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 126.05(14) . . ?
O1 C1 C5 126.31(13) . . ?
C2 C1 C5 107.58(12) . . ?
C3 C2 C6 131.34(13) . . ?
C3 C2 C1 106.49(13) . . ?
C6 C2 C1 122.11(13) . . ?
C2 C3 C12 126.85(13) . . ?
C2 C3 C4 109.77(12) . . ?
C12 C3 C4 123.36(13) . . ?
C5 C4 C18 127.27(13) . . ?
C5 C4 C3 109.54(13) . . ?
C18 C4 C3 123.19(12) . . ?
C4 C5 C24 131.51(14) . . ?
C4 C5 C1 106.44(12) . . ?
C24 C5 C1 121.80(13) . . ?
C7 C6 C11 117.78(14) . . ?
C7 C6 C2 121.29(13) . . ?
C11 C6 C2 120.92(13) . . ?
C8 C7 C6 120.68(15) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C9 C8 C7 120.82(16) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 119.24(15) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 120.37(15) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C6 121.06(15) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
C13 C12 C17 118.79(13) . . ?
C13 C12 C3 119.07(13) . . ?
C17 C12 C3 122.13(13) . . ?
C14 C13 C12 120.65(14) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.03(14) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 119.85(13) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.20(14) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 120.42(14) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C23 C18 C19 118.92(14) . . ?
C23 C18 C4 119.90(13) . . ?
C19 C18 C4 121.18(13) . . ?
C20 C19 C18 120.22(15) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.36(16) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 119.53(15) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C23 C22 C21 120.41(16) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C18 120.53(15) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
C29 C24 C25 118.26(13) . . ?
C29 C24 C5 120.07(14) . . ?
C25 C24 C5 121.60(13) . . ?
C26 C25 C24 120.77(14) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C27 120.33(15) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C28 C27 C26 119.55(14) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C27 C28 C29 120.36(14) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C28 C29 C24 120.71(15) . . ?
C28 C29 H29 119.6 . . ?
C24 C29 H29 119.6 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.061
