# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_red
_database_code_depnum_ccdc_archive 'CCDC 1418487'
_audit_update_record             
;
2015-08-13 deposited with the CCDC.
2015-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H25 O'
_chemical_formula_weight         353.46

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           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8637(10)
_cell_length_b                   11.7729(16)
_cell_length_c                   13.2710(19)
_cell_angle_alpha                64.589(7)
_cell_angle_beta                 84.416(8)
_cell_angle_gamma                82.273(9)
_cell_volume                     958.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             378
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13185
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3343
_reflns_number_gt                2502
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.1000P)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         3343
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1513
_refine_ls_wR_factor_gt          0.1393
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          1.418
_refine_ls_shift/su_mean         0.042

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
O2 O -0.11300(16) 0.46251(11) 0.64086(10) 0.0563(4) Uani 1 1 d . . .
C7 C 1.0646(3) 0.1067(2) 1.1668(2) 0.0864(7) Uani 1 1 d . . .
H7A H 1.1497 0.1717 1.1494 0.130 Uiso 1 1 calc R . .
H7B H 1.1332 0.0399 1.1499 0.130 Uiso 1 1 calc R . .
H7C H 1.0256 0.0738 1.2447 0.130 Uiso 1 1 calc R . .
C1 C 0.8852(2) 0.16122(15) 1.09841(17) 0.0575(5) Uani 1 1 d . . .
C6 C 0.7166(3) 0.21227(16) 1.13714(16) 0.0575(5) Uani 1 1 d . . .
H6 H 0.7135 0.2104 1.2081 0.069 Uiso 1 1 calc R . .
C5 C 0.5540(2) 0.26557(15) 1.07356(14) 0.0498(4) Uani 1 1 d . . .
H5 H 0.4438 0.2990 1.1023 0.060 Uiso 1 1 calc R . .
C4 C 0.5510(2) 0.27048(14) 0.96714(13) 0.0448(4) Uani 1 1 d . . .
C8 C 0.3842(2) 0.33482(14) 0.89585(13) 0.0443(4) Uani 1 1 d . . .
C12 C 0.2928(2) 0.44946(15) 0.87962(13) 0.0473(4) Uani 1 1 d . . .
H12 H 0.3234 0.4950 0.9174 0.057 Uiso 1 1 calc R . .
C11 C 0.1370(2) 0.49711(14) 0.79488(13) 0.0435(4) Uani 1 1 d . . .
C13 C 0.1928(2) 0.61673(14) 0.69429(13) 0.0424(4) Uani 1 1 d . . .
C14 C 0.3895(2) 0.63010(16) 0.65816(14) 0.0529(5) Uani 1 1 d . . .
H14 H 0.4855 0.5658 0.6962 0.063 Uiso 1 1 calc R . .
C15 C 0.4456(3) 0.73575(17) 0.56774(16) 0.0585(5) Uani 1 1 d . . .
H15 H 0.5783 0.7410 0.5460 0.070 Uiso 1 1 calc R . .
C16 C 0.3083(3) 0.83476(16) 0.50826(14) 0.0536(5) Uani 1 1 d . . .
C19 C 0.3706(3) 0.94952(18) 0.40798(16) 0.0763(6) Uani 1 1 d . . .
H19A H 0.4998 0.9648 0.4178 0.114 Uiso 1 1 calc R . .
H19B H 0.2792 1.0217 0.4003 0.114 Uiso 1 1 calc R . .
H19C H 0.3724 0.9350 0.3420 0.114 Uiso 1 1 calc R . .
C18 C 0.0567(2) 0.71504(15) 0.63457(15) 0.0499(4) Uani 1 1 d . . .
H18 H -0.0762 0.7101 0.6558 0.060 Uiso 1 1 calc R . .
C17 C 0.1151(3) 0.82108(16) 0.54339(15) 0.0556(5) Uani 1 1 d . . .
H17 H 0.0193 0.8852 0.5047 0.067 Uiso 1 1 calc R . .
C10 C 0.1478(2) 0.38479(14) 0.76423(13) 0.0425(4) Uani 1 1 d . . .
C25 C 0.2934(2) 0.29131(14) 0.82361(13) 0.0436(4) Uani 1 1 d . . .
C2 C 0.8807(3) 0.16354(16) 0.99367(18) 0.0607(5) Uani 1 1 d . . .
H2 H 0.9897 0.1278 0.9660 0.073 Uiso 1 1 calc R . .
C3 C 0.7198(2) 0.21718(16) 0.92954(15) 0.0558(5) Uani 1 1 d . . .
H3 H 0.7231 0.2181 0.8590 0.067 Uiso 1 1 calc R . .
C24 C 0.3208(2) 0.17669(15) 0.81399(14) 0.0501(4) Uani 1 1 d . . .
C23 C 0.2091(3) 0.16206(16) 0.74102(16) 0.0562(5) Uani 1 1 d . . .
H23 H 0.2304 0.0876 0.7313 0.067 Uiso 1 1 calc R . .
C22 C 0.0655(3) 0.25496(16) 0.68156(15) 0.0540(5) Uani 1 1 d . . .
H22 H -0.0087 0.2419 0.6332 0.065 Uiso 1 1 calc R . .
C21 C 0.0311(2) 0.36750(15) 0.69344(13) 0.0450(4) Uani 1 1 d . . .
C26 C -0.2389(3) 0.44087(19) 0.57313(16) 0.0654(5) Uani 1 1 d . . .
H26A H -0.1611 0.4210 0.5175 0.098 Uiso 1 1 calc R . .
H26B H -0.3275 0.5155 0.5372 0.098 Uiso 1 1 calc R . .
H26C H -0.3132 0.3715 0.6190 0.098 Uiso 1 1 calc R . .
C20 C -0.0650(2) 0.51642(17) 0.85070(15) 0.0554(5) Uani 1 1 d . . .
H20A H -0.0881 0.4406 0.9161 0.083 Uiso 1 1 calc R . .
H20B H -0.1665 0.5354 0.7992 0.083 Uiso 1 1 calc R . .
H20C H -0.0661 0.5852 0.8715 0.083 Uiso 1 1 calc R . .
O1 O 0.4542(2) 0.07869(11) 0.87668(13) 0.0710(4) Uani 1 1 d . . .
H1 H 0.4279 0.0124 0.8774 0.107 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
O2 C21 1.3721(19) . ?
O2 C26 1.4238(19) . ?
C7 C1 1.502(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C1 C2 1.382(3) . ?
C1 C6 1.388(3) . ?
C6 C5 1.376(2) . ?
C6 H6 0.9300 . ?
C5 C4 1.391(2) . ?
C5 H5 0.9300 . ?
C4 C3 1.395(2) . ?
C4 C8 1.464(2) . ?
C8 C12 1.346(2) . ?
C8 C25 1.481(2) . ?
C12 C11 1.502(2) . ?
C12 H12 0.9300 . ?
C11 C13 1.531(2) . ?
C11 C10 1.533(2) . ?
C11 C20 1.544(2) . ?
C13 C18 1.381(2) . ?
C13 C14 1.394(2) . ?
C14 C15 1.376(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.389(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.370(2) . ?
C16 C19 1.510(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C18 C17 1.388(2) . ?
C18 H18 0.9300 . ?
C17 H17 0.9300 . ?
C10 C21 1.386(2) . ?
C10 C25 1.394(2) . ?
C25 C24 1.396(2) . ?
C2 C3 1.370(3) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C24 C23 1.371(2) . ?
C24 O1 1.379(2) . ?
C23 C22 1.382(2) . ?
C23 H23 0.9300 . ?
C22 C21 1.387(2) . ?
C22 H22 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O1 H1 0.8201 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 O2 C26 117.13(13) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C1 C6 116.88(17) . . ?
C2 C1 C7 121.50(18) . . ?
C6 C1 C7 121.62(19) . . ?
C5 C6 C1 121.83(18) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
C6 C5 C4 121.31(16) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C4 C3 116.50(16) . . ?
C5 C4 C8 121.68(14) . . ?
C3 C4 C8 121.72(15) . . ?
C12 C8 C4 125.24(14) . . ?
C12 C8 C25 107.53(14) . . ?
C4 C8 C25 127.12(14) . . ?
C8 C12 C11 113.84(14) . . ?
C8 C12 H12 123.1 . . ?
C11 C12 H12 123.1 . . ?
C12 C11 C13 110.47(12) . . ?
C12 C11 C10 100.16(12) . . ?
C13 C11 C10 111.44(12) . . ?
C12 C11 C20 109.76(13) . . ?
C13 C11 C20 113.06(13) . . ?
C10 C11 C20 111.21(12) . . ?
C18 C13 C14 116.57(15) . . ?
C18 C13 C11 123.37(14) . . ?
C14 C13 C11 120.07(14) . . ?
C15 C14 C13 121.85(16) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 121.41(16) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C17 C16 C15 116.66(16) . . ?
C17 C16 C19 122.19(17) . . ?
C15 C16 C19 121.13(17) . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 C18 C17 121.06(16) . . ?
C13 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C16 C17 C18 122.45(16) . . ?
C16 C17 H17 118.8 . . ?
C18 C17 H17 118.8 . . ?
C21 C10 C25 121.30(14) . . ?
C21 C10 C11 128.61(15) . . ?
C25 C10 C11 110.02(13) . . ?
C10 C25 C24 119.87(15) . . ?
C10 C25 C8 108.42(13) . . ?
C24 C25 C8 131.52(16) . . ?
C3 C2 C1 121.61(17) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 121.83(17) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C23 C24 O1 119.89(14) . . ?
C23 C24 C25 118.36(16) . . ?
O1 C24 C25 121.74(16) . . ?
C24 C23 C22 121.76(15) . . ?
C24 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
C23 C22 C21 120.59(16) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
O2 C21 C10 117.62(14) . . ?
O2 C21 C22 124.35(15) . . ?
C10 C21 C22 118.02(16) . . ?
O2 C26 H26A 109.5 . . ?
O2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C11 C20 H20A 109.5 . . ?
C11 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C11 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C24 O1 H1 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C6 C5 -1.5(3) . . . . ?
C7 C1 C6 C5 178.07(15) . . . . ?
C1 C6 C5 C4 0.1(3) . . . . ?
C6 C5 C4 C3 0.9(2) . . . . ?
C6 C5 C4 C8 -175.64(14) . . . . ?
C5 C4 C8 C12 45.1(2) . . . . ?
C3 C4 C8 C12 -131.17(18) . . . . ?
C5 C4 C8 C25 -139.03(16) . . . . ?
C3 C4 C8 C25 44.7(2) . . . . ?
C4 C8 C12 C11 175.20(13) . . . . ?
C25 C8 C12 C11 -1.31(18) . . . . ?
C8 C12 C11 C13 -116.14(15) . . . . ?
C8 C12 C11 C10 1.46(16) . . . . ?
C8 C12 C11 C20 118.53(16) . . . . ?
C12 C11 C13 C18 -145.66(14) . . . . ?
C10 C11 C13 C18 103.92(16) . . . . ?
C20 C11 C13 C18 -22.2(2) . . . . ?
C12 C11 C13 C14 34.82(18) . . . . ?
C10 C11 C13 C14 -75.61(17) . . . . ?
C20 C11 C13 C14 158.27(14) . . . . ?
C18 C13 C14 C15 0.0(2) . . . . ?
C11 C13 C14 C15 179.60(14) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C17 -0.7(3) . . . . ?
C14 C15 C16 C19 -179.02(16) . . . . ?
C14 C13 C18 C17 0.0(2) . . . . ?
C11 C13 C18 C17 -179.50(13) . . . . ?
C15 C16 C17 C18 0.8(2) . . . . ?
C19 C16 C17 C18 179.10(16) . . . . ?
C13 C18 C17 C16 -0.5(3) . . . . ?
C12 C11 C10 C21 176.01(15) . . . . ?
C13 C11 C10 C21 -67.11(19) . . . . ?
C20 C11 C10 C21 60.0(2) . . . . ?
C12 C11 C10 C25 -1.06(15) . . . . ?
C13 C11 C10 C25 115.82(14) . . . . ?
C20 C11 C10 C25 -117.04(15) . . . . ?
C21 C10 C25 C24 -1.3(2) . . . . ?
C11 C10 C25 C24 176.00(13) . . . . ?
C21 C10 C25 C8 -176.92(13) . . . . ?
C11 C10 C25 C8 0.40(17) . . . . ?
C12 C8 C25 C10 0.54(18) . . . . ?
C4 C8 C25 C10 -175.88(13) . . . . ?
C12 C8 C25 C24 -174.37(16) . . . . ?
C4 C8 C25 C24 9.2(3) . . . . ?
C6 C1 C2 C3 1.9(2) . . . . ?
C7 C1 C2 C3 -177.67(15) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C5 C4 C3 C2 -0.5(2) . . . . ?
C8 C4 C3 C2 176.04(14) . . . . ?
C10 C25 C24 C23 3.4(2) . . . . ?
C8 C25 C24 C23 177.82(15) . . . . ?
C10 C25 C24 O1 -175.72(13) . . . . ?
C8 C25 C24 O1 -1.3(3) . . . . ?
O1 C24 C23 C22 176.08(15) . . . . ?
C25 C24 C23 C22 -3.1(3) . . . . ?
C24 C23 C22 C21 0.6(3) . . . . ?
C26 O2 C21 C10 -176.68(14) . . . . ?
C26 O2 C21 C22 2.4(2) . . . . ?
C25 C10 C21 O2 177.96(13) . . . . ?
C11 C10 C21 O2 1.2(2) . . . . ?
C25 C10 C21 C22 -1.2(2) . . . . ?
C11 C10 C21 C22 -177.96(14) . . . . ?
C23 C22 C21 O2 -177.50(14) . . . . ?
C23 C22 C21 C10 1.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.031
####################################################################### 
# 
# 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_kck552
_database_code_depnum_ccdc_archive 'CCDC 1418498'
_audit_update_record             
;
2015-08-13 deposited with the CCDC.
2015-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H24 O4'
_chemical_formula_weight         388.44

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                   17.682
_cell_length_b                   10.244
_cell_length_c                   11.523
_cell_angle_alpha                90.00
_cell_angle_beta                 97.04
_cell_angle_gamma                90.00
_cell_volume                     2071.4
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.998
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   BRUKARSADBAS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            19327
_diffrn_reflns_av_R_equivalents  0.0939
_diffrn_reflns_av_sigmaI/netI    0.0680
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.16
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3646
_reflns_number_gt                1897
_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)+(0.0344P)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         3646
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0898
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   0.820
_refine_ls_restrained_S_all      0.820
_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 0.33751(6) 0.54771(11) 0.42058(10) 0.0604(3) Uani 1 1 d . . .
C9 C 0.32863(10) 0.64541(16) 0.33697(15) 0.0495(5) Uani 1 1 d . . .
C7 C 0.20439(9) 0.72239(16) 0.40022(14) 0.0498(5) Uani 1 1 d . . .
C6 C 0.21759(10) 0.60977(16) 0.48638(14) 0.0503(5) Uani 1 1 d . . .
C1 C 0.28006(10) 0.52977(17) 0.49092(15) 0.0515(5) Uani 1 1 d . . .
C10 C 0.39276(10) 0.64501(17) 0.26636(15) 0.0494(4) Uani 1 1 d . . .
O2 O 0.24331(8) 0.29839(14) 0.71978(11) 0.0834(4) Uani 1 1 d . . .
C8 C 0.26900(10) 0.72388(17) 0.32620(15) 0.0555(5) Uani 1 1 d . . .
H8 H 0.2666 0.7862 0.2672 0.067 Uiso 1 1 calc R . .
C2 C 0.29199(11) 0.42452(17) 0.56685(15) 0.0595(5) Uani 1 1 d . . .
H2 H 0.3350 0.3722 0.5670 0.071 Uiso 1 1 calc R . .
C16 C 0.12984(10) 0.70035(16) 0.31939(14) 0.0491(5) Uani 1 1 d . . .
C19 C -0.00099(11) 0.65449(19) 0.16225(16) 0.0576(5) Uani 1 1 d . . .
C13 C 0.51268(11) 0.6402(2) 0.12942(17) 0.0621(5) Uani 1 1 d . . .
C4 C 0.17591(12) 0.47847(19) 0.64135(16) 0.0661(5) Uani 1 1 d . . .
H4 H 0.1405 0.4624 0.6930 0.079 Uiso 1 1 calc R . .
C15 C 0.39771(10) 0.73611(17) 0.17816(15) 0.0567(5) Uani 1 1 d . . .
H15 H 0.3601 0.7997 0.1645 0.068 Uiso 1 1 calc R . .
C11 C 0.44937(11) 0.55220(18) 0.28297(16) 0.0682(6) Uani 1 1 d . . .
H11 H 0.4476 0.4898 0.3412 0.082 Uiso 1 1 calc R . .
C5 C 0.16564(11) 0.58087(19) 0.56456(15) 0.0628(5) Uani 1 1 d . . .
H5 H 0.1226 0.6329 0.5645 0.075 Uiso 1 1 calc R . .
C3 C 0.23919(12) 0.39910(19) 0.64170(16) 0.0614(5) Uani 1 1 d . . .
C21 C 0.06879(10) 0.78421(18) 0.31044(16) 0.0645(5) Uani 1 1 d . . .
H21 H 0.0711 0.8579 0.3579 0.077 Uiso 1 1 calc R . .
C14 C 0.45657(11) 0.73485(18) 0.11063(16) 0.0618(5) Uani 1 1 d . . .
H14 H 0.4587 0.7973 0.0525 0.074 Uiso 1 1 calc R . .
C17 C 0.12299(10) 0.59171(17) 0.24732(14) 0.0550(5) Uani 1 1 d . . .
H17 H 0.1630 0.5324 0.2517 0.066 Uiso 1 1 calc R . .
C18 C 0.05897(10) 0.56852(17) 0.16951(15) 0.0573(5) Uani 1 1 d . . .
H18 H 0.0563 0.4949 0.1220 0.069 Uiso 1 1 calc R . .
C20 C 0.00367(11) 0.76213(19) 0.23263(17) 0.0713(6) Uani 1 1 d . . .
H20 H -0.0368 0.8207 0.2285 0.086 Uiso 1 1 calc R . .
C12 C 0.50882(11) 0.54932(19) 0.21532(18) 0.0741(6) Uani 1 1 d . . .
H12 H 0.5462 0.4854 0.2283 0.089 Uiso 1 1 calc R . .
O3 O -0.06256(7) 0.62335(13) 0.08222(11) 0.0796(4) Uani 1 1 d . . .
O4 O 0.56858(8) 0.64580(14) 0.05674(12) 0.0849(4) Uani 1 1 d . . .
C25 C 0.62461(12) 0.5443(2) 0.06745(18) 0.0945(7) Uani 1 1 d . . .
H25A H 0.6527 0.5469 0.1442 0.142 Uiso 1 1 calc R . .
H25B H 0.6589 0.5567 0.0099 0.142 Uiso 1 1 calc R . .
H25C H 0.5998 0.4611 0.0554 0.142 Uiso 1 1 calc R . .
C24 C 0.20491(10) 0.85284(16) 0.46652(15) 0.0667(6) Uani 1 1 d . . .
H24A H 0.1631 0.8548 0.5123 0.100 Uiso 1 1 calc R . .
H24B H 0.2000 0.9236 0.4115 0.100 Uiso 1 1 calc R . .
H24C H 0.2520 0.8615 0.5171 0.100 Uiso 1 1 calc R . .
C26 C -0.11872(12) 0.7189(2) 0.05354(19) 0.1022(8) Uani 1 1 d . . .
H26A H -0.1429 0.7395 0.1215 0.153 Uiso 1 1 calc R . .
H26B H -0.1561 0.6865 -0.0070 0.153 Uiso 1 1 calc R . .
H26C H -0.0956 0.7962 0.0265 0.153 Uiso 1 1 calc R . .
C27 C 0.30164(14) 0.2053(2) 0.71672(19) 0.0973(8) Uani 1 1 d . . .
H27A H 0.2945 0.1598 0.6433 0.146 Uiso 1 1 calc R . .
H27B H 0.3000 0.1440 0.7794 0.146 Uiso 1 1 calc R . .
H27C H 0.3502 0.2485 0.7253 0.146 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 1.3847(18) . ?
O1 C1 1.3872(19) . ?
C9 C8 1.320(2) . ?
C9 C10 1.474(2) . ?
C7 C8 1.507(2) . ?
C7 C6 1.521(2) . ?
C7 C16 1.535(2) . ?
C7 C24 1.539(2) . ?
C6 C1 1.371(2) . ?
C6 C5 1.395(2) . ?
C1 C2 1.388(2) . ?
C10 C11 1.377(2) . ?
C10 C15 1.390(2) . ?
O2 C3 1.365(2) . ?
O2 C27 1.409(2) . ?
C2 C3 1.371(2) . ?
C16 C21 1.374(2) . ?
C16 C17 1.385(2) . ?
C19 C20 1.365(2) . ?
C19 C18 1.373(2) . ?
C19 O3 1.3752(19) . ?
C13 C12 1.367(2) . ?
C13 O4 1.373(2) . ?
C13 C14 1.385(2) . ?
C4 C5 1.370(2) . ?
C4 C3 1.383(2) . ?
C15 C14 1.374(2) . ?
C11 C12 1.384(2) . ?
C21 C20 1.388(2) . ?
C17 C18 1.376(2) . ?
O3 C26 1.405(2) . ?
O4 C25 1.431(2) . ?

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 118.27(14) . . ?
C8 C9 O1 121.79(17) . . ?
C8 C9 C10 127.55(17) . . ?
O1 C9 C10 110.66(15) . . ?
C8 C7 C6 108.10(14) . . ?
C8 C7 C16 108.20(13) . . ?
C6 C7 C16 109.64(14) . . ?
C8 C7 C24 108.26(14) . . ?
C6 C7 C24 110.09(13) . . ?
C16 C7 C24 112.43(14) . . ?
C1 C6 C5 116.09(17) . . ?
C1 C6 C7 122.44(16) . . ?
C5 C6 C7 121.46(16) . . ?
C6 C1 O1 122.87(16) . . ?
C6 C1 C2 123.20(17) . . ?
O1 C1 C2 113.93(17) . . ?
C11 C10 C15 117.08(17) . . ?
C11 C10 C9 121.36(17) . . ?
C15 C10 C9 121.54(16) . . ?
C3 O2 C27 118.39(16) . . ?
C9 C8 C7 126.37(17) . . ?
C3 C2 C1 118.77(18) . . ?
C21 C16 C17 116.58(16) . . ?
C21 C16 C7 124.21(16) . . ?
C17 C16 C7 119.18(15) . . ?
C20 C19 C18 119.47(18) . . ?
C20 C19 O3 124.81(18) . . ?
C18 C19 O3 115.72(17) . . ?
C12 C13 O4 125.01(18) . . ?
C12 C13 C14 119.45(18) . . ?
O4 C13 C14 115.54(19) . . ?
C5 C4 C3 119.68(18) . . ?
C14 C15 C10 121.85(17) . . ?
C10 C11 C12 121.74(18) . . ?
C4 C5 C6 122.28(18) . . ?
O2 C3 C2 124.94(19) . . ?
O2 C3 C4 115.09(18) . . ?
C2 C3 C4 119.97(18) . . ?
C16 C21 C20 121.90(17) . . ?
C15 C14 C13 119.73(18) . . ?
C18 C17 C16 122.27(16) . . ?
C19 C18 C17 119.77(17) . . ?
C19 C20 C21 120.01(18) . . ?
C13 C12 C11 120.15(18) . . ?
C19 O3 C26 118.34(15) . . ?
C13 O4 C25 117.37(16) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.026
