# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# 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_st627
_audit_block_doi                 10.5517/cc93fzs
_database_code_depnum_ccdc_archive 'CCDC 271435'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/ejoc.200500339 2005
_audit_update_record             
;
2005-05-09 deposited with the CCDC.
2014-12-09 downloaded from the CCDC.
;

_audit_creation_date             22-05-00


#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H22 O3'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C15 H22 O3'
_chemical_formula_weight         250.34
_chemical_melting_point          ?
_chemical_compound_source        ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C ? 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1
H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1
O ? 0.008 0.006 International_Tables_Vol_IV_Table_2.3.1


#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
_cell_length_a                   10.7927(7)
_cell_length_b                   11.6842(8)
_cell_length_c                   12.384(1)
_cell_angle_alpha                81.436(5)
_cell_angle_beta                 87.887(5)
_cell_angle_gamma                69.366(5)
_cell_volume                     1445.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173
_cell_measurement_reflns_used    9351
_cell_measurement_theta_min      1.4
_cell_measurement_theta_max      27.6
_cell_special_details            
;
Cell parameters refined using Scalepack part of DENZO
Z. Otwinowski, W. Minor, 1997
;

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.15
_exptl_crystal_density_method    none

_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
#===============================================================================

# 7. EXPERIMENTAL DATA

_diffrn_special_details          
; ?
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           Mo-K\a

_diffrn_source                   xray_tube

_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'π scans'

_diffrn_measurement_details      
;
9351 reflections were collected using program Collect
("Collect" Data collection software, Nonius B.V., 1998)
The conditions were as follow : crystal to detector distance = 36. mm.
Scan angle = 2.0 deg 1 scans of 90 sec per frame.
Data collection was divided into 3 set(s)
with the following starting angles and number of frames :

Set 1 Theta = 6.40 Omega = 0.00 Kappa = 0.00 91 frames
Set 2 Theta = 4.20 Kappa = 127.00 Phi = 0.00 18 frames
Set 3 Theta = -6.40 Kappa = -172.00 Phi = 0.00 19 frames
Friedel pairs were averaged. Internal R = 0.05
;

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0

_diffrn_reflns_number            9351
_diffrn_reflns_av_R_equivalents  0.050
_diffrn_reflns_av_sigmaI/netI    0.333
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.5
_diffrn_reflns_theta_max         27.56

_reflns_number_total             6537
_reflns_number_gt                2643
_reflns_threshold_expression     >3.0σ(I)

_computing_structure_solution    Direct_methods_(SIR,_Burla_et_al.,_1989)
_computing_structure_refinement  LSFM_OpenMoleN_(_1997)
_computing_molecular_graphics    ?
_computing_publication_material  CIFGEN_IN_OpenMoleN_(_1997)

#===============================================================================

# 8. REFINEMENT DATA


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      '4Fo^2^/(\s^2^(Fo^2^) + 0.0064 Fo^4^)'
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_expression ?
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         2643
_refine_ls_number_parameters     325
_refine_ls_number_restraints     8
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.151
_refine_ls_R_factor_gt           0.051
_refine_ls_wR_factor_all         0.239
_refine_ls_wR_factor_ref         0.070
_refine_ls_goodness_of_fit_all   4.197
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_shift/su_max          0.002
_refine_ls_shift/esd_mean        0.000
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.108

#===============================================================================

# 9. ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_type_symbol
C1 1.3486(2) 0.1776(2) 0.3703(2) 0.034(1) Uani ? ? C
C2 1.3270(3) 0.1545(3) 0.4908(3) 0.044(2) Uani ? ? C
C3 1.1802(3) 0.2154(3) 0.5152(3) 0.052(2) Uani ? ? C
C4 1.1292(3) 0.3520(3) 0.4683(3) 0.044(2) Uani ? ? C
C5 1.1540(2) 0.3732(2) 0.3456(3) 0.035(1) Uani ? ? C
C6 1.1015(3) 0.5092(3) 0.2959(3) 0.052(2) Uani ? ? C
C7 1.1240(3) 0.5288(3) 0.1738(4) 0.071(2) Uani ? ? C
C8 1.2700(4) 0.4695(3) 0.1498(3) 0.071(2) Uani ? ? C
C9 1.3229(3) 0.3329(3) 0.1968(3) 0.053(2) Uani ? ? C
C10 1.3016(2) 0.3130(2) 0.3201(2) 0.034(1) Uani ? ? C
O1 1.3713(1) 0.3732(2) 0.3744(2) 0.038(1) Uani ? ? O
C11 1.4006(2) 0.0905(2) 0.3087(3) 0.038(1) Uani ? ? C
C12 1.4575(3) 0.0023(2) 0.2486(3) 0.044(2) Uani ? ? C
C13 1.6005(3) -0.0361(2) 0.2284(3) 0.041(1) Uani ? ? C
O2 1.6741(2) 0.0137(2) 0.2545(2) 0.048(1) Uani ? ? O
O3 1.6420(2) -0.1344(2) 0.1764(2) 0.059(1) Uani ? ? O
C14 1.7822(3) -0.1819(3) 0.1486(3) 0.065(2) Uani ? ? C
C15 1.7941(3) -0.2267(3) 0.0438(3) 0.060(2) Uani ? ? C
C16 0.8329(2) 0.2518(2) 0.2439(2) 0.035(1) Uani ? ? C
C17 0.7610(3) 0.3654(3) 0.1652(3) 0.052(2) Uani ? ? C
C18 0.7343(3) 0.4828(3) 0.2173(3) 0.058(2) Uani ? ? C
C19 0.6660(3) 0.4759(3) 0.3272(3) 0.047(2) Uani ? ? C
C20 0.7409(2) 0.3602(2) 0.4044(2) 0.034(1) Uani ? ? C
C21 0.6784(3) 0.3517(3) 0.5164(3) 0.049(2) Uani ? ? C
C22 0.7557(3) 0.2371(3) 0.5938(3) 0.057(2) Uani ? ? C
C23 0.7749(3) 0.1210(3) 0.5426(3) 0.048(2) Uani ? ? C
C24 0.8414(2) 0.1255(2) 0.4328(2) 0.036(1) Uani ? ? C
C25 0.7648(2) 0.2408(2) 0.3530(2) 0.031(1) Uani ? ? C
O4 0.6349(2) 0.2390(2) 0.3306(2) 0.0356(9) Uani ? ? O
C26 0.9483(2) 0.1724(2) 0.2225(2) 0.037(1) Uani ? ? C
C27 1.0654(2) 0.0972(2) 0.1998(2) 0.037(1) Uani ? ? C
C28 1.0851(2) -0.0124(3) 0.1468(3) 0.040(1) Uani ? ? C
O5 1.0017(2) -0.0533(2) 0.1282(2) 0.072(1) Uani ? ? O
O6 1.2132(2) -0.0640(2) 0.1203(2) 0.042(1) Uani ? ? O
C29 1.2466(3) -0.1708(3) 0.0632(3) 0.058(2) Uani ? ? C
C30 1.3920(4) -0.2175(4) 0.0478(4) 0.081(2) Uani ? ? C
H01 1.4638 0.3291 0.3615 0.0532 Uiso ? ? H
H02 0.6417 0.1664 0.3054 0.0532 Uiso ? ? H
H1 1.3778 0.1884 0.5285 0.0598 Uiso calc C2 H
H2 1.3539 0.0680 0.5143 0.0598 Uiso calc C2 H
H3 1.1690 0.2071 0.5921 0.0668 Uiso calc C3 H
H4 1.1309 0.1751 0.4838 0.0668 Uiso calc C3 H
H5 1.1729 0.3933 0.5048 0.0596 Uiso calc C4 H
H6 1.0367 0.3851 0.4801 0.0596 Uiso calc C4 H
H7 1.1051 0.3341 0.3122 0.0483 Uiso calc C5 H
H8 1.1451 0.5520 0.3306 0.0761 Uiso calc C6 H
H9 1.0091 0.5419 0.3084 0.0761 Uiso calc C6 H
H10 1.0957 0.6149 0.1481 0.1016 Uiso calc C7 H
H11 1.0744 0.4924 0.1376 0.1016 Uiso calc C7 H
H12 1.3184 0.5106 0.1813 0.0988 Uiso calc C8 H
H13 1.2813 0.4778 0.0730 0.0988 Uiso calc C8 H
H14 1.4150 0.3001 0.1831 0.0698 Uiso calc C9 H
H15 1.2783 0.2909 0.1620 0.0698 Uiso calc C9 H
H16 1.4058 -0.0364 0.2181 0.0568 Uiso calc C12 H
H17 1.8292 -0.2477 0.2033 0.0890 Uiso calc C14 H
H18 1.8177 -0.1177 0.1439 0.0890 Uiso calc C14 H
H19 1.8848 -0.2578 0.0250 0.0807 Uiso calc C15 H
H20 1.7583 -0.2909 0.0487 0.0807 Uiso calc C15 H
H21 1.7468 -0.1608 -0.0107 0.0807 Uiso calc C15 H
H22 0.6791 0.3612 0.1444 0.0709 Uiso calc C17 H
H23 0.8136 0.3686 0.1023 0.0709 Uiso calc C17 H
H24 0.6790 0.5518 0.1693 0.0824 Uiso calc C18 H
H25 0.8162 0.4932 0.2281 0.0824 Uiso calc C18 H
H26 0.5795 0.4763 0.3151 0.0631 Uiso calc C19 H
H27 0.6602 0.5461 0.3600 0.0631 Uiso calc C19 H
H28 0.8244 0.3668 0.4161 0.0436 Uiso calc C20 H
H29 0.5917 0.3511 0.5070 0.0616 Uiso calc C21 H
H30 0.6733 0.4224 0.5482 0.0616 Uiso calc C21 H
H31 0.7085 0.2340 0.6598 0.0771 Uiso calc C22 H
H32 0.8399 0.2405 0.6090 0.0771 Uiso calc C22 H
H33 0.6909 0.1145 0.5329 0.0657 Uiso calc C23 H
H34 0.8286 0.0508 0.5903 0.0657 Uiso calc C23 H
H35 0.8471 0.0541 0.4020 0.0462 Uiso calc C24 H
H36 0.9280 0.1258 0.4437 0.0462 Uiso calc C24 H
H37 1.1412 0.1141 0.2184 0.0479 Uiso calc C27 H
H38 1.2023 -0.1474 -0.0058 0.0745 Uiso calc C29 H
H39 1.2208 -0.2333 0.1053 0.0745 Uiso calc C29 H
H40 1.4159 -0.2875 0.0105 0.1098 Uiso calc C30 H
H41 1.4173 -0.1545 0.0059 0.1098 Uiso calc C30 H
H42 1.4359 -0.2404 0.1170 0.1098 Uiso calc C30 H



# 10. MOLECULAR GEOMETRY



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.500(5) . . ?
C1 C10 1.520(4) . . ?
C1 C11 1.315(5) . . ?
C2 C3 1.530(5) . . ?
C3 C4 1.522(5) . . ?
C4 C5 1.531(5) . . ?
C5 C6 1.524(5) . . ?
C5 C10 1.540(4) . . ?
C6 C7 1.518(6) . . ?
C7 C8 1.519(6) . . ?
C8 C9 1.523(5) . . ?
C9 C10 1.531(5) . . ?
C10 O1 1.437(3) . . ?
C10 H01 1.9208 . . ?
O1 H01 0.9681 . . ?
C11 C12 1.320(5) . . ?
C12 C13 1.471(4) . . ?
C13 O2 1.215(3) . . ?
C13 O3 1.330(4) . . ?
O2 H02 1.8924 . ._655 ?
O3 C14 1.464(4) . . ?
C14 C15 1.455(6) . . ?
C16 C17 1.502(5) . . ?
C16 C25 1.525(4) . . ?
C16 C26 1.311(4) . . ?
C17 C18 1.534(6) . . ?
C18 C19 1.530(6) . . ?
C19 C20 1.516(5) . . ?
C20 C21 1.525(5) . . ?
C20 C25 1.553(4) . . ?
C21 C22 1.516(5) . . ?
C22 C23 1.526(5) . . ?
C23 C24 1.517(5) . . ?
C24 C25 1.534(4) . . ?
C25 O4 1.448(3) . . ?
C25 H02 1.9740 . . ?
O4 H01 1.8337 . ._455 ?
O4 H02 0.9250 . . ?
C26 C27 1.309(4) . . ?
C27 C28 1.472(5) . . ?
C28 O5 1.201(4) . . ?
C28 O6 1.350(4) . . ?
O6 C29 1.453(4) . . ?
C29 C30 1.484(5) . . ?

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
? ? ? ? ? ?

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C10 115.0(3) . . . ?
C2 C1 C11 124.6(3) . . . ?
C10 C1 C11 120.3(3) . . . ?
C1 C2 C3 109.8(3) . . . ?
C2 C3 C4 111.1(3) . . . ?
C3 C4 C5 112.1(3) . . . ?
C4 C5 C6 113.3(3) . . . ?
C4 C5 C10 111.4(3) . . . ?
C6 C5 C10 110.8(3) . . . ?
C5 C6 C7 112.7(4) . . . ?
C6 C7 C8 110.2(3) . . . ?
C7 C8 C9 111.4(3) . . . ?
C8 C9 C10 111.5(3) . . . ?
C1 C10 C5 108.7(2) . . . ?
C1 C10 C9 113.5(3) . . . ?
C1 C10 O1 107.8(2) . . . ?
C1 C10 H01 91.68 . . . ?
C5 C10 C9 110.3(3) . . . ?
C5 C10 O1 106.4(2) . . . ?
C5 C10 H01 135.56 . . . ?
C9 C10 O1 109.8(2) . . . ?
C9 C10 H01 95.78 . . . ?
O1 C10 H01 29.24 . . . ?
C10 O1 H01 104.29 . . . ?
C1 C11 C12 177.7(3) . . . ?
C11 C12 C13 120.3(3) . . . ?
C12 C13 O2 125.7(3) . . . ?
C12 C13 O3 111.5(3) . . . ?
O2 C13 O3 122.8(3) . . . ?
C13 O2 H02 132.29 . . ._655 ?
C13 O3 C14 117.8(3) . . . ?
O3 C14 C15 108.8(3) . . . ?
C17 C16 C25 114.6(3) . . . ?
C17 C16 C26 122.5(3) . . . ?
C25 C16 C26 122.8(3) . . . ?
C16 C17 C18 111.0(3) . . . ?
C17 C18 C19 111.8(3) . . . ?
C18 C19 C20 112.1(3) . . . ?
C19 C20 C21 113.8(3) . . . ?
C19 C20 C25 112.1(3) . . . ?
C21 C20 C25 111.0(3) . . . ?
C20 C21 C22 113.3(3) . . . ?
C21 C22 C23 110.4(3) . . . ?
C22 C23 C24 111.3(3) . . . ?
C23 C24 C25 112.3(3) . . . ?
C16 C25 C20 108.7(2) . . . ?
C16 C25 C24 113.6(3) . . . ?
C16 C25 O4 107.5(2) . . . ?
C16 C25 H02 96.89 . . . ?
C20 C25 C24 110.8(3) . . . ?
C20 C25 O4 106.0(2) . . . ?
C20 C25 H02 131.91 . . . ?
C24 C25 O4 109.8(2) . . . ?
C24 C25 H02 93.93 . . . ?
O4 C25 H02 26.01 . . . ?
C25 O4 H01 135.99 . . ._455 ?
C25 O4 H02 110.63 . . . ?
H01 O4 H02 112.29 . ._455 . ?
C16 C26 C27 177.4(3) . . . ?
C26 C27 C28 123.0(3) . . . ?
C27 C28 O5 126.6(3) . . . ?
C27 C28 O6 110.6(3) . . . ?
O5 C28 O6 122.9(3) . . . ?
C28 O6 C29 116.7(2) . . . ?
O6 C29 C30 108.2(3) . . . ?
C10 H01 O1 46.48 . . . ?
C10 H01 O4 129.30 . . ._655 ?
O1 H01 O4 175.77 . . ._655 ?
O2 H02 C25 130.95 . ._455 . ?
O2 H02 O4 174.30 . ._455 . ?
C25 H02 O4 43.36 . . . ?



####################################################################### 
# 
# 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/. 
# 
# 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_e2769a
_database_code_depnum_ccdc_archive 'CCDC 1005688'
_audit_update_record             
;
2014-05-28 deposited with the CCDC.
2014-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H22 O3'
_chemical_formula_sum            'C15 H22 O3'
_chemical_formula_weight         250.33

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)/n
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   9.8087(18)
_cell_length_b                   6.9137(12)
_cell_length_c                   20.582(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.156(5)
_cell_angle_gamma                90.00
_cell_volume                     1384.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1092
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      24.30

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9967
_exptl_absorpt_correction_T_max  0.9984
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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            9887
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_sigmaI/netI    0.1008
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         30.04
_reflns_number_total             4044
_reflns_number_gt                1819
_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)+(0.0550P)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         4044
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1575
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1432
_refine_ls_wR_factor_gt          0.1137
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.003

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7460(2) 0.9994(3) 0.10331(9) 0.0315(5) Uani 1 1 d . . .
O1 O 0.62729(14) 1.12152(18) 0.09263(6) 0.0358(4) Uani 1 1 d . . .
H1 H 0.5745 1.0968 0.1207 0.054 Uiso 1 1 calc R . .
C2 C 0.7049(2) 0.7883(3) 0.11172(10) 0.0365(5) Uani 1 1 d . . .
H2A H 0.7889 0.7094 0.1225 0.044 Uiso 1 1 calc R . .
H2B H 0.6502 0.7788 0.1489 0.044 Uiso 1 1 calc R . .
C3 C 0.6213(2) 0.7063(3) 0.05048(10) 0.0451(6) Uani 1 1 d . . .
H3A H 0.5312 0.7725 0.0431 0.054 Uiso 1 1 calc R . .
H3B H 0.6043 0.5669 0.0570 0.054 Uiso 1 1 calc R . .
C4 C 0.6960(3) 0.7325(3) -0.00955(11) 0.0533(7) Uani 1 1 d . . .
H4A H 0.6362 0.6882 -0.0490 0.064 Uiso 1 1 calc R . .
H4B H 0.7802 0.6520 -0.0048 0.064 Uiso 1 1 calc R . .
C5 C 0.7348(3) 0.9432(3) -0.01808(10) 0.0513(6) Uani 1 1 d . . .
H5A H 0.7867 0.9550 -0.0562 0.062 Uiso 1 1 calc R . .
H5B H 0.6502 1.0217 -0.0271 0.062 Uiso 1 1 calc R . .
C6 C 0.8217(2) 1.0208(3) 0.04267(10) 0.0392(5) Uani 1 1 d . . .
H6 H 0.9063 0.9389 0.0501 0.047 Uiso 1 1 calc R . .
C7 C 0.8688(3) 1.2306(3) 0.03442(11) 0.0498(6) Uani 1 1 d . . .
H7A H 0.9189 1.2387 -0.0044 0.060 Uiso 1 1 calc R . .
H7B H 0.7871 1.3154 0.0265 0.060 Uiso 1 1 calc R . .
C8 C 0.9609(3) 1.3026(3) 0.09390(12) 0.0533(7) Uani 1 1 d . . .
H8A H 0.9833 1.4404 0.0876 0.064 Uiso 1 1 calc R . .
H8B H 1.0479 1.2284 0.0988 0.064 Uiso 1 1 calc R . .
C9 C 0.8922(2) 1.2812(3) 0.15578(11) 0.0426(6) Uani 1 1 d . . .
H9A H 0.9587 1.3137 0.1945 0.051 Uiso 1 1 calc R . .
H9B H 0.8140 1.3723 0.1543 0.051 Uiso 1 1 calc R . .
C10 C 0.8412(2) 1.0764(3) 0.16210(10) 0.0314(5) Uani 1 1 d . . .
C11 C 0.8812(2) 0.9680(3) 0.21217(10) 0.0329(5) Uani 1 1 d . . .
C12 C 0.9195(2) 0.8524(3) 0.26185(10) 0.0355(5) Uani 1 1 d . . .
H12 H 0.8695 0.8577 0.2985 0.043 Uiso 1 1 calc R . .
C13 C 1.0342(2) 0.7163(3) 0.26427(9) 0.0336(5) Uani 1 1 d . . .
O2 O 1.06180(15) 0.6020(2) 0.30862(7) 0.0445(4) Uani 1 1 d . . .
O3 O 1.10457(14) 0.72976(17) 0.21292(6) 0.0330(3) Uani 1 1 d . . .
C14 C 1.2203(2) 0.6004(3) 0.21241(10) 0.0344(5) Uani 1 1 d . . .
H14A H 1.1885 0.4644 0.2101 0.041 Uiso 1 1 calc R . .
H14B H 1.2852 0.6170 0.2529 0.041 Uiso 1 1 calc R . .
C15 C 1.2897(2) 0.6489(3) 0.15354(10) 0.0436(6) Uani 1 1 d . . .
H15A H 1.2258 0.6266 0.1137 0.065 Uiso 1 1 calc R . .
H15B H 1.3709 0.5668 0.1529 0.065 Uiso 1 1 calc R . .
H15C H 1.3176 0.7851 0.1556 0.065 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
C1 O1 1.433(2) . ?
C1 C10 1.529(3) . ?
C1 C2 1.530(3) . ?
C1 C6 1.537(3) . ?
O1 H1 0.8400 . ?
C2 C3 1.525(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.524(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.521(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.521(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.538(3) . ?
C6 H6 1.0000 . ?
C7 C8 1.512(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.521(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.513(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.295(3) . ?
C11 C12 1.315(3) . ?
C12 C13 1.463(3) . ?
C12 H12 0.9500 . ?
C13 O2 1.212(2) . ?
C13 O3 1.336(2) . ?
O3 C14 1.446(2) . ?
C14 C15 1.500(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
O1 C1 C10 108.68(14) . . ?
O1 C1 C2 111.02(16) . . ?
C10 C1 C2 112.72(15) . . ?
O1 C1 C6 106.53(14) . . ?
C10 C1 C6 107.47(17) . . ?
C2 C1 C6 110.17(16) . . ?
C1 O1 H1 109.5 . . ?
C3 C2 C1 112.56(16) . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 111.22(19) . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 C5 111.09(17) . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C4 111.44(17) . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 C7 112.79(17) . . ?
C5 C6 C1 110.83(18) . . ?
C7 C6 C1 111.26(16) . . ?
C5 C6 H6 107.2 . . ?
C7 C6 H6 107.2 . . ?
C1 C6 H6 107.2 . . ?
C8 C7 C6 112.23(18) . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C9 111.33(19) . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 110.42(17) . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 122.64(18) . . ?
C11 C10 C1 121.53(16) . . ?
C9 C10 C1 115.71(16) . . ?
C10 C11 C12 177.9(2) . . ?
C11 C12 C13 124.15(19) . . ?
C11 C12 H12 117.9 . . ?
C13 C12 H12 117.9 . . ?
O2 C13 O3 123.48(19) . . ?
O2 C13 C12 122.97(19) . . ?
O3 C13 C12 113.55(17) . . ?
C13 O3 C14 116.51(14) . . ?
O3 C14 C15 107.63(15) . . ?
O3 C14 H14A 110.2 . . ?
C15 C14 H14A 110.2 . . ?
O3 C14 H14B 110.2 . . ?
C15 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        30.04
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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/. 
# 
# 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_e2998a
_database_code_depnum_ccdc_archive 'CCDC 1005689'
_audit_update_record             
;
2014-05-28 deposited with the CCDC.
2014-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H22 O3'
_chemical_formula_sum            'C15 H22 O3'
_chemical_formula_weight         250.33

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)/n
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   7.8484(2)
_cell_length_b                   19.3484(4)
_cell_length_c                   17.9841(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.4260(10)
_cell_angle_gamma                90.00
_cell_volume                     2726.08(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7392
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      29.44

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9942
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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            32208
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         30.05
_reflns_number_total             7963
_reflns_number_gt                5739
_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)+(0.0906P)²+1.5301P] 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         7963
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.1829
_refine_ls_wR_factor_gt          0.1616
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0839(2) 0.20490(8) 0.12522(8) 0.0213(3) Uani 1 1 d . . .
O1 O -0.08064(17) 0.17320(6) 0.19743(6) 0.0273(3) Uani 1 1 d . . .
H1 H -0.0520 0.2026 0.2301 0.041 Uiso 1 1 calc R . .
C2 C -0.1780(2) 0.27490(9) 0.12839(10) 0.0293(4) Uani 1 1 d . . .
H2A H -0.2840 0.2683 0.1548 0.035 Uiso 1 1 calc R . .
H2B H -0.1049 0.3079 0.1578 0.035 Uiso 1 1 calc R . .
C3 C -0.2236(3) 0.30616(10) 0.05295(12) 0.0356(4) Uani 1 1 d . . .
H3A H -0.1179 0.3193 0.0291 0.043 Uiso 1 1 calc R . .
H3B H -0.2920 0.3486 0.0591 0.043 Uiso 1 1 calc R . .
C4 C -0.3250(3) 0.25544(11) 0.00317(13) 0.0391(5) Uani 1 1 d . . .
H4A H -0.4357 0.2456 0.0246 0.047 Uiso 1 1 calc R . .
H4B H -0.3484 0.2761 -0.0468 0.047 Uiso 1 1 calc R . .
C5 C -0.2256(3) 0.18866(11) -0.00394(11) 0.0345(4) Uani 1 1 d . . .
H5A H -0.1183 0.1984 -0.0283 0.041 Uiso 1 1 calc R . .
H5B H -0.2936 0.1561 -0.0361 0.041 Uiso 1 1 calc R . .
C6 C -0.1830(2) 0.15486(9) 0.07193(9) 0.0246(3) Uani 1 1 d . . .
H6 H -0.2940 0.1447 0.0943 0.030 Uiso 1 1 calc R . .
C7 C -0.0904(3) 0.08655(10) 0.06550(11) 0.0329(4) Uani 1 1 d . . .
H7A H -0.1566 0.0565 0.0299 0.040 Uiso 1 1 calc R . .
H7B H -0.0842 0.0633 0.1146 0.040 Uiso 1 1 calc R . .
C8 C 0.0907(3) 0.09525(10) 0.03936(12) 0.0347(4) Uani 1 1 d . . .
H8A H 0.1479 0.0497 0.0385 0.042 Uiso 1 1 calc R . .
H8B H 0.0853 0.1143 -0.0118 0.042 Uiso 1 1 calc R . .
C9 C 0.1932(2) 0.14413(10) 0.09204(12) 0.0316(4) Uani 1 1 d . . .
H9A H 0.2148 0.1213 0.1410 0.038 Uiso 1 1 calc R . .
H9B H 0.3049 0.1539 0.0715 0.038 Uiso 1 1 calc R . .
C10 C 0.0995(2) 0.21174(9) 0.10274(9) 0.0232(3) Uani 1 1 d . . .
C11 C 0.1746(2) 0.27097(10) 0.09487(9) 0.0262(3) Uani 1 1 d . . .
C12 C 0.2511(2) 0.32941(9) 0.08219(10) 0.0279(4) Uani 1 1 d . . .
H12 H 0.2323 0.3494 0.0342 0.033 Uiso 1 1 calc R . .
C13 C 0.3646(2) 0.36672(10) 0.13703(11) 0.0310(4) Uani 1 1 d . . .
O2 O 0.4487(2) 0.41548(9) 0.12081(10) 0.0541(5) Uani 1 1 d . . .
O3 O 0.3720(2) 0.33826(9) 0.20492(9) 0.0499(4) Uani 1 1 d . . .
C14 C 0.4993(4) 0.36552(14) 0.25985(16) 0.0548(7) Uani 1 1 d . . .
H14A H 0.6065 0.3746 0.2351 0.066 Uiso 1 1 calc R . .
H14B H 0.5238 0.3302 0.2988 0.066 Uiso 1 1 calc R . .
C15 C 0.4438(4) 0.4299(2) 0.2955(2) 0.0803(11) Uani 1 1 d . . .
H15A H 0.4216 0.4655 0.2574 0.120 Uiso 1 1 calc R . .
H15B H 0.5337 0.4459 0.3316 0.120 Uiso 1 1 calc R . .
H15C H 0.3392 0.4211 0.3211 0.120 Uiso 1 1 calc R . .
C16 C 0.1143(2) 0.40599(8) 0.80111(8) 0.0203(3) Uani 1 1 d . . .
O4 O 0.21898(16) 0.43745(6) 0.74778(7) 0.0276(3) Uani 1 1 d . . .
H4 H 0.2858 0.4078 0.7318 0.041 Uiso 1 1 calc R . .
C17 C 0.0068(2) 0.34890(9) 0.76303(10) 0.0257(3) Uani 1 1 d . . .
H17A H -0.0416 0.3665 0.7146 0.031 Uiso 1 1 calc R . .
H17B H 0.0827 0.3096 0.7526 0.031 Uiso 1 1 calc R . .
C18 C -0.1391(2) 0.32219(10) 0.80757(12) 0.0309(4) Uani 1 1 d . . .
H18A H -0.0919 0.2973 0.8523 0.037 Uiso 1 1 calc R . .
H18B H -0.2094 0.2893 0.7768 0.037 Uiso 1 1 calc R . .
C19 C -0.2505(2) 0.38205(10) 0.83130(12) 0.0325(4) Uani 1 1 d . . .
H19A H -0.3068 0.4041 0.7867 0.039 Uiso 1 1 calc R . .
H19B H -0.3405 0.3643 0.8626 0.039 Uiso 1 1 calc R . .
C20 C -0.1417(2) 0.43525(9) 0.87511(10) 0.0284(4) Uani 1 1 d . . .
H20A H -0.0908 0.4135 0.9210 0.034 Uiso 1 1 calc R . .
H20B H -0.2155 0.4737 0.8900 0.034 Uiso 1 1 calc R . .
C21 C 0.0012(2) 0.46414(8) 0.82964(9) 0.0230(3) Uani 1 1 d . . .
H21 H -0.0550 0.4871 0.7848 0.028 Uiso 1 1 calc R . .
C22 C 0.1067(2) 0.51963(9) 0.87206(10) 0.0283(4) Uani 1 1 d . . .
H22A H 0.1782 0.5440 0.8369 0.034 Uiso 1 1 calc R . .
H22B H 0.0283 0.5540 0.8924 0.034 Uiso 1 1 calc R . .
C23 C 0.2215(2) 0.49023(9) 0.93578(10) 0.0277(4) Uani 1 1 d . . .
H23A H 0.1503 0.4697 0.9737 0.033 Uiso 1 1 calc R . .
H23B H 0.2901 0.5279 0.9598 0.033 Uiso 1 1 calc R . .
C24 C 0.3403(2) 0.43510(9) 0.90692(9) 0.0237(3) Uani 1 1 d . . .
H24A H 0.4205 0.4566 0.8733 0.028 Uiso 1 1 calc R . .
H24B H 0.4079 0.4139 0.9492 0.028 Uiso 1 1 calc R . .
C25 C 0.2360(2) 0.37989(8) 0.86520(8) 0.0192(3) Uani 1 1 d . . .
C26 C 0.2510(2) 0.31462(9) 0.88056(9) 0.0209(3) Uani 1 1 d . . .
C27 C 0.2636(2) 0.24831(8) 0.89625(9) 0.0220(3) Uani 1 1 d . . .
H27 H 0.1982 0.2294 0.9341 0.026 Uiso 1 1 calc R . .
C28 C 0.3774(2) 0.20303(8) 0.85601(9) 0.0218(3) Uani 1 1 d . . .
O5 O 0.46720(18) 0.22020(7) 0.80692(7) 0.0317(3) Uani 1 1 d . . .
O6 O 0.36718(17) 0.13800(6) 0.88080(7) 0.0296(3) Uani 1 1 d . . .
C29 C 0.4635(3) 0.08620(11) 0.84291(12) 0.0428(5) Uani 1 1 d . . .
H29A H 0.5735 0.1058 0.8288 0.051 Uiso 1 1 calc R . .
H29B H 0.3985 0.0708 0.7970 0.051 Uiso 1 1 calc R . .
C30 C 0.4947(3) 0.02690(10) 0.89404(13) 0.0402(5) Uani 1 1 d . . .
H30A H 0.5573 0.0427 0.9396 0.060 Uiso 1 1 calc R . .
H30B H 0.5620 -0.0082 0.8697 0.060 Uiso 1 1 calc R . .
H30C H 0.3852 0.0070 0.9066 0.060 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
C1 O1 1.4350(19) . ?
C1 C10 1.524(2) . ?
C1 C6 1.540(2) . ?
C1 C2 1.545(2) . ?
O1 H1 0.8400 . ?
C2 C3 1.509(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.521(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.519(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.532(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.516(3) . ?
C6 H6 1.0000 . ?
C7 C8 1.533(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.532(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.518(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.300(2) . ?
C11 C12 1.307(2) . ?
C12 C13 1.478(3) . ?
C12 H12 0.9500 . ?
C13 O2 1.197(2) . ?
C13 O3 1.337(3) . ?
O3 C14 1.461(3) . ?
C14 C15 1.479(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 O4 1.4352(19) . ?
C16 C17 1.527(2) . ?
C16 C25 1.538(2) . ?
C16 C21 1.540(2) . ?
O4 H4 0.8400 . ?
C17 C18 1.526(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.527(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.526(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.533(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.531(2) . ?
C21 H21 1.0000 . ?
C22 C23 1.525(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.528(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.517(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.297(2) . ?
C26 C27 1.316(2) . ?
C27 C28 1.472(2) . ?
C27 H27 0.9500 . ?
C28 O5 1.209(2) . ?
C28 O6 1.339(2) . ?
O6 C29 1.450(2) . ?
C29 C30 1.481(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 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
O1 C1 C10 108.14(13) . . ?
O1 C1 C6 105.98(13) . . ?
C10 C1 C6 109.85(13) . . ?
O1 C1 C2 108.90(13) . . ?
C10 C1 C2 113.26(13) . . ?
C6 C1 C2 110.43(14) . . ?
C1 O1 H1 109.5 . . ?
C3 C2 C1 113.98(15) . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C2 C3 C4 111.00(16) . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C3 110.20(16) . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C6 111.95(17) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C5 112.59(15) . . ?
C7 C6 C1 111.64(15) . . ?
C5 C6 C1 111.16(14) . . ?
C7 C6 H6 107.0 . . ?
C5 C6 H6 107.0 . . ?
C1 C6 H6 107.0 . . ?
C6 C7 C8 112.66(15) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 109.90(15) . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C10 C9 C8 111.70(15) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 121.30(16) . . ?
C11 C10 C1 123.14(16) . . ?
C9 C10 C1 115.53(14) . . ?
C10 C11 C12 176.09(18) . . ?
C11 C12 C13 124.85(17) . . ?
C11 C12 H12 117.6 . . ?
C13 C12 H12 117.6 . . ?
O2 C13 O3 123.53(19) . . ?
O2 C13 C12 122.79(19) . . ?
O3 C13 C12 113.56(15) . . ?
C13 O3 C14 117.34(18) . . ?
O3 C14 C15 113.0(2) . . ?
O3 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
O3 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 C17 109.27(13) . . ?
O4 C16 C25 106.57(13) . . ?
C17 C16 C25 113.60(13) . . ?
O4 C16 C21 106.09(12) . . ?
C17 C16 C21 111.36(14) . . ?
C25 C16 C21 109.56(12) . . ?
C16 O4 H4 109.5 . . ?
C18 C17 C16 114.91(14) . . ?
C18 C17 H17A 108.5 . . ?
C16 C17 H17A 108.5 . . ?
C18 C17 H17B 108.5 . . ?
C16 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C17 C18 C19 110.49(15) . . ?
C17 C18 H18A 109.6 . . ?
C19 C18 H18A 109.6 . . ?
C17 C18 H18B 109.6 . . ?
C19 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
C20 C19 C18 110.09(15) . . ?
C20 C19 H19A 109.6 . . ?
C18 C19 H19A 109.6 . . ?
C20 C19 H19B 109.6 . . ?
C18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.2 . . ?
C19 C20 C21 112.06(15) . . ?
C19 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C22 C21 C20 112.40(14) . . ?
C22 C21 C16 111.93(14) . . ?
C20 C21 C16 111.46(14) . . ?
C22 C21 H21 106.9 . . ?
C20 C21 H21 106.9 . . ?
C16 C21 H21 106.9 . . ?
C23 C22 C21 112.97(14) . . ?
C23 C22 H22A 109.0 . . ?
C21 C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
C21 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 C24 110.51(14) . . ?
C22 C23 H23A 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 108.1 . . ?
C25 C24 C23 109.72(14) . . ?
C25 C24 H24A 109.7 . . ?
C23 C24 H24A 109.7 . . ?
C25 C24 H24B 109.7 . . ?
C23 C24 H24B 109.7 . . ?
H24A C24 H24B 108.2 . . ?
C26 C25 C24 122.77(15) . . ?
C26 C25 C16 121.58(15) . . ?
C24 C25 C16 115.61(13) . . ?
C25 C26 C27 179.12(18) . . ?
C26 C27 C28 120.99(15) . . ?
C26 C27 H27 119.5 . . ?
C28 C27 H27 119.5 . . ?
O5 C28 O6 123.41(15) . . ?
O5 C28 C27 126.37(15) . . ?
O6 C28 C27 110.21(14) . . ?
C28 O6 C29 116.74(14) . . ?
O6 C29 C30 108.36(17) . . ?
O6 C29 H29A 110.0 . . ?
C30 C29 H29A 110.0 . . ?
O6 C29 H29B 110.0 . . ?
C30 C29 H29B 110.0 . . ?
H29A C29 H29B 108.4 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.05
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.705
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.061
