# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_2
_audit_block_doi                 10.5517/cc131xhk
_database_code_depnum_ccdc_archive 'CCDC 1014738'
_audit_update_record             
;
2014-12-04 deposited with the CCDC.
2015-02-03 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
_chemical_absolute_configuration unk

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0000 '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 0.0492 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   6.896(1)
_cell_length_b                   7.706(1)
_cell_length_c                   13.516(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.435(5)
_cell_angle_gamma                90.00
_cell_volume                     713.72(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    295
_cell_measurement_reflns_used    1024
_cell_measurement_theta_min      6.46
_cell_measurement_theta_max      64.20

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_type   none

_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2883
_diffrn_reflns_av_R_equivalents  0.0910
_diffrn_reflns_av_sigmaI/netI    0.1355
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         6.46
_diffrn_reflns_theta_max         64.93
_reflns_number_total             1232
_reflns_number_gt                780
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0792P)²+0.5987P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.013(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details '507 Friedel pairs merged'
_refine_ls_number_reflns         1232
_refine_ls_number_parameters     166
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1585
_refine_ls_R_factor_gt           0.0885
_refine_ls_wR_factor_ref         0.2846
_refine_ls_wR_factor_gt          0.2198
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_restrained_S_all      1.197
_refine_ls_shift/su_max          0.01
_refine_ls_shift/su_mean         0.01

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 0.4891(8) 0.4997(10) 0.4340(4) 0.0718(19) Uani 1 1 d . . .
O2 O 0.3573(9) 0.4994(12) 0.5765(4) 0.082(2) Uani 1 1 d . . .
O3 O 0.6206(8) 0.3117(12) 0.3271(4) 0.083(2) Uani 1 1 d . . .
H3 H 0.6498 0.2498 0.3777 0.124 Uiso 1 1 calc R . .
C1 C 0.3594(13) 0.4442(13) 0.4927(6) 0.066(3) Uani 1 1 d . . .
C2 C 0.2260(11) 0.3159(14) 0.4405(6) 0.063(2) Uani 1 1 d . . .
C3 C 0.2815(12) 0.2972(14) 0.3501(6) 0.063(2) Uani 1 1 d . . .
C4 C 0.4555(11) 0.4090(16) 0.3395(6) 0.068(3) Uani 1 1 d . . .
C5 C 0.0723(12) 0.2240(18) 0.4925(6) 0.078(3) Uani 1 1 d . . .
H5A H -0.0097 0.1533 0.4442 0.118 Uiso 1 1 calc R . .
H5B H -0.0088 0.3100 0.5219 0.118 Uiso 1 1 calc R . .
H5C H 0.1358 0.1491 0.5451 0.118 Uiso 1 1 calc R . .
C6 C 0.2082(13) 0.1995(15) 0.2587(6) 0.067(3) Uani 1 1 d . . .
H6 H 0.3132 0.1162 0.2451 0.080 Uiso 1 1 calc R . .
C7 C 0.0159(13) 0.0965(18) 0.2511(6) 0.078(3) Uani 1 1 d . . .
H7A H -0.0878 0.1634 0.2790 0.094 Uiso 1 1 calc R . .
H7B H 0.0337 -0.0158 0.2866 0.094 Uiso 1 1 calc R . .
C8 C -0.0338(16) 0.069(2) 0.1379(7) 0.106(4) Uani 1 1 d . . .
H8A H -0.1740 0.0913 0.1176 0.127 Uiso 1 1 calc R . .
H8B H -0.0042 -0.0522 0.1195 0.127 Uiso 1 1 calc R . .
C9 C 0.0965(18) 0.200(2) 0.0856(8) 0.106(4) Uani 1 1 d . . .
H9 H 0.0105 0.2694 0.0357 0.127 Uiso 1 1 calc R . .
C10 C 0.251(2) 0.109(3) 0.0325(10) 0.150(7) Uani 1 1 d . . .
H10A H 0.3302 0.1955 0.0023 0.224 Uiso 1 1 calc R . .
H10B H 0.1870 0.0332 -0.0196 0.224 Uiso 1 1 calc R . .
H10C H 0.3347 0.0392 0.0805 0.224 Uiso 1 1 calc R . .
C11 C 0.1778(15) 0.3215(18) 0.1704(6) 0.083(3) Uani 1 1 d . . .
H11 H 0.0699 0.4023 0.1831 0.100 Uiso 1 1 calc R . .
C12 C 0.3573(16) 0.4340(17) 0.1587(6) 0.086(3) Uani 1 1 d . . .
H12A H 0.4653 0.3587 0.1420 0.103 Uiso 1 1 calc R . .
H12B H 0.3258 0.5162 0.1029 0.103 Uiso 1 1 calc R . .
C13 C 0.4239(15) 0.5354(16) 0.2527(6) 0.078(3) Uani 1 1 d . . .
C14 C 0.6147(16) 0.635(2) 0.2382(8) 0.101(4) Uani 1 1 d . . .
H14A H 0.7158 0.5525 0.2239 0.151 Uiso 1 1 calc R . .
H14B H 0.6590 0.6996 0.2991 0.151 Uiso 1 1 calc R . .
H14C H 0.5894 0.7165 0.1825 0.151 Uiso 1 1 calc R . .
C15 C 0.2712(18) 0.6789(19) 0.2748(9) 0.100(4) Uani 1 1 d . . .
H15A H 0.1481 0.6233 0.2867 0.149 Uiso 1 1 calc R . .
H15B H 0.2483 0.7571 0.2175 0.149 Uiso 1 1 calc R . .
H15C H 0.3223 0.7454 0.3338 0.149 Uiso 1 1 calc R . .


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 1.331(10) . ?
O1 C4 1.451(10) . ?
O2 C1 1.212(9) . ?
O3 C4 1.389(11) . ?
O3 H3 0.8400 . ?
C1 C2 1.475(13) . ?
C2 C3 1.329(10) . ?
C2 C5 1.512(13) . ?
C3 C6 1.485(12) . ?
C3 C4 1.497(13) . ?
C4 C13 1.522(13) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C11 1.516(14) . ?
C6 C7 1.539(13) . ?
C6 H6 1.0000 . ?
C7 C8 1.546(12) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.576(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.522(18) . ?
C9 C11 1.533(16) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.534(14) . ?
C11 H11 1.0000 . ?
C12 C13 1.517(13) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.556(14) . ?
C13 C15 1.579(16) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
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
C1 O1 C4 108.6(7) . . ?
C4 O3 H3 109.5 . . ?
O2 C1 O1 121.6(9) . . ?
O2 C1 C2 127.6(9) . . ?
O1 C1 C2 110.8(7) . . ?
C3 C2 C1 106.5(8) . . ?
C3 C2 C5 131.8(9) . . ?
C1 C2 C5 121.6(7) . . ?
C2 C3 C6 135.5(9) . . ?
C2 C3 C4 110.0(8) . . ?
C6 C3 C4 114.5(7) . . ?
O3 C4 O1 108.3(6) . . ?
O3 C4 C3 112.2(10) . . ?
O1 C4 C3 104.1(6) . . ?
O3 C4 C13 107.5(7) . . ?
O1 C4 C13 111.4(9) . . ?
C3 C4 C13 113.2(7) . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 C11 110.2(9) . . ?
C3 C6 C7 121.8(7) . . ?
C11 C6 C7 103.0(7) . . ?
C3 C6 H6 107.0 . . ?
C11 C6 H6 107.0 . . ?
C7 C6 H6 107.0 . . ?
C6 C7 C8 103.4(8) . . ?
C6 C7 H7A 111.1 . . ?
C8 C7 H7A 111.1 . . ?
C6 C7 H7B 111.1 . . ?
C8 C7 H7B 111.1 . . ?
H7A C7 H7B 109.0 . . ?
C7 C8 C9 106.2(9) . . ?
C7 C8 H8A 110.5 . . ?
C9 C8 H8A 110.5 . . ?
C7 C8 H8B 110.5 . . ?
C9 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
C10 C9 C11 114.7(10) . . ?
C10 C9 C8 112.1(15) . . ?
C11 C9 C8 103.7(8) . . ?
C10 C9 H9 108.7 . . ?
C11 C9 H9 108.7 . . ?
C8 C9 H9 108.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 C9 102.6(11) . . ?
C6 C11 C12 112.9(7) . . ?
C9 C11 C12 119.9(8) . . ?
C6 C11 H11 106.9 . . ?
C9 C11 H11 106.9 . . ?
C12 C11 H11 106.9 . . ?
C13 C12 C11 112.1(7) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 C4 108.7(9) . . ?
C12 C13 C14 109.3(8) . . ?
C4 C13 C14 111.3(8) . . ?
C12 C13 C15 111.9(8) . . ?
C4 C13 C15 110.1(7) . . ?
C14 C13 C15 105.6(10) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C4 O1 C1 O2 179.5(9) . . . . ?
C4 O1 C1 C2 -1.7(10) . . . . ?
O2 C1 C2 C3 179.0(10) . . . . ?
O1 C1 C2 C3 0.3(11) . . . . ?
O2 C1 C2 C5 -5.0(15) . . . . ?
O1 C1 C2 C5 176.2(9) . . . . ?
C1 C2 C3 C6 -175.9(10) . . . . ?
C5 C2 C3 C6 8.7(19) . . . . ?
C1 C2 C3 C4 1.2(10) . . . . ?
C5 C2 C3 C4 -174.2(10) . . . . ?
C1 O1 C4 O3 -117.3(8) . . . . ?
C1 O1 C4 C3 2.2(9) . . . . ?
C1 O1 C4 C13 124.6(8) . . . . ?
C2 C3 C4 O3 114.8(8) . . . . ?
C6 C3 C4 O3 -67.5(9) . . . . ?
C2 C3 C4 O1 -2.1(10) . . . . ?
C6 C3 C4 O1 175.6(8) . . . . ?
C2 C3 C4 C13 -123.3(9) . . . . ?
C6 C3 C4 C13 54.5(11) . . . . ?
C2 C3 C6 C11 125.6(12) . . . . ?
C4 C3 C6 C11 -51.4(10) . . . . ?
C2 C3 C6 C7 4.9(17) . . . . ?
C4 C3 C6 C7 -172.1(9) . . . . ?
C3 C6 C7 C8 162.5(10) . . . . ?
C11 C6 C7 C8 38.5(11) . . . . ?
C6 C7 C8 C9 -15.9(13) . . . . ?
C7 C8 C9 C10 112.3(11) . . . . ?
C7 C8 C9 C11 -12.0(13) . . . . ?
C3 C6 C11 C9 -178.1(8) . . . . ?
C7 C6 C11 C9 -46.6(10) . . . . ?
C3 C6 C11 C12 51.5(11) . . . . ?
C7 C6 C11 C12 -177.1(9) . . . . ?
C10 C9 C11 C6 -86.8(14) . . . . ?
C8 C9 C11 C6 35.8(11) . . . . ?
C10 C9 C11 C12 39.2(17) . . . . ?
C8 C9 C11 C12 161.8(10) . . . . ?
C6 C11 C12 C13 -55.0(12) . . . . ?
C9 C11 C12 C13 -176.1(10) . . . . ?
C11 C12 C13 C4 54.2(11) . . . . ?
C11 C12 C13 C14 175.8(9) . . . . ?
C11 C12 C13 C15 -67.6(12) . . . . ?
O3 C4 C13 C12 70.6(10) . . . . ?
O1 C4 C13 C12 -170.9(7) . . . . ?
C3 C4 C13 C12 -53.9(11) . . . . ?
O3 C4 C13 C14 -49.8(11) . . . . ?
O1 C4 C13 C14 68.8(10) . . . . ?
C3 C4 C13 C14 -174.3(9) . . . . ?
O3 C4 C13 C15 -166.5(9) . . . . ?
O1 C4 C13 C15 -48.0(10) . . . . ?
C3 C4 C13 C15 69.0(10) . . . . ?

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 H3 O2 0.84 2.03 2.732(12) 141.0 2_646

_diffrn_measured_fraction_theta_max 0.943
_diffrn_reflns_theta_full        64.93
_diffrn_measured_fraction_theta_full 0.943
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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_9
_audit_block_doi                 10.5517/cc131xkm
_database_code_depnum_ccdc_archive 'CCDC 1014740'
_audit_update_record             
;
2014-12-04 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H24 O2'
_chemical_formula_sum            'C15 H24 O2'
_chemical_formula_weight         236.34
_chemical_absolute_configuration unk

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0000 '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 0.0492 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   7.5653(2)
_cell_length_b                   10.7212(4)
_cell_length_c                   16.5230(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1340.17(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    295
_cell_measurement_reflns_used    3679
_cell_measurement_theta_min      4.92
_cell_measurement_theta_max      66.49

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_type   none

_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5876
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.92
_diffrn_reflns_theta_max         64.98
_reflns_number_total             1323
_reflns_number_gt                1237
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0981P)²+0.0756P] 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_abs_structure_details '905 Friedel pairs merged'
_refine_ls_number_reflns         1323
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1450
_refine_ls_wR_factor_gt          0.1206
_refine_ls_goodness_of_fit_ref   1.216
_refine_ls_restrained_S_all      1.216
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

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 0.7831(3) 0.0008(2) 0.79696(14) 0.0655(6) Uani 1 1 d . . .
H1 H 0.6853 0.0367 0.7911 0.098 Uiso 1 1 calc R . .
O2 O 1.4921(2) 0.1806(2) 0.79774(13) 0.0640(6) Uani 1 1 d . . .
C1 C 0.8847(3) 0.0650(3) 0.85684(15) 0.0444(6) Uani 1 1 d . . .
H1A H 0.8062 0.1240 0.8845 0.053 Uiso 1 1 calc R . .
C2 C 1.0316(3) 0.1387(2) 0.81796(13) 0.0422(6) Uani 1 1 d . . .
C3 C 1.1999(3) 0.1339(2) 0.84507(14) 0.0384(6) Uani 1 1 d . . .
C4 C 1.2582(3) 0.0543(2) 0.91744(13) 0.0367(5) Uani 1 1 d . . .
C5 C 1.0927(3) 0.0301(2) 0.97014(13) 0.0382(5) Uani 1 1 d . . .
H5 H 1.0476 0.1135 0.9829 0.046 Uiso 1 1 calc R . .
C6 C 0.9478(3) -0.0292(3) 0.91858(15) 0.0444(6) Uani 1 1 d . . .
H6A H 0.9935 -0.1025 0.8913 0.053 Uiso 1 1 calc R . .
H6B H 0.8500 -0.0547 0.9528 0.053 Uiso 1 1 calc R . .
C7 C 0.9677(4) 0.2173(4) 0.74767(18) 0.0622(8) Uani 1 1 d . . .
H7A H 0.9746 0.1696 0.6986 0.093 Uiso 1 1 calc R . .
H7B H 1.0406 0.2903 0.7429 0.093 Uiso 1 1 calc R . .
H7C H 0.8474 0.2420 0.7570 0.093 Uiso 1 1 calc R . .
C8 C 1.3347(4) 0.2019(3) 0.79812(17) 0.0502(7) Uani 1 1 d . . .
H8 H 1.2953 0.2673 0.7658 0.060 Uiso 1 1 calc R . .
C9 C 1.3473(4) -0.0642(3) 0.88411(17) 0.0499(7) Uani 1 1 d . . .
H9A H 1.4357 -0.0413 0.8452 0.075 Uiso 1 1 calc R . .
H9B H 1.2601 -0.1161 0.8586 0.075 Uiso 1 1 calc R . .
H9C H 1.4017 -0.1092 0.9277 0.075 Uiso 1 1 calc R . .
C10 C 1.3902(3) 0.1293(3) 0.97050(16) 0.0491(7) Uani 1 1 d . . .
H10A H 1.4998 0.1404 0.9409 0.059 Uiso 1 1 calc R . .
H10B H 1.3414 0.2113 0.9813 0.059 Uiso 1 1 calc R . .
C11 C 1.4292(4) 0.0644(3) 1.05052(18) 0.0605(8) Uani 1 1 d . . .
H11A H 1.4859 -0.0151 1.0399 0.073 Uiso 1 1 calc R . .
H11B H 1.5106 0.1150 1.0818 0.073 Uiso 1 1 calc R . .
C12 C 1.2622(4) 0.0427(3) 1.09938(16) 0.0575(8) Uani 1 1 d . . .
H12A H 1.2128 0.1229 1.1145 0.069 Uiso 1 1 calc R . .
H12B H 1.2928 -0.0012 1.1488 0.069 Uiso 1 1 calc R . .
C13 C 1.1214(4) -0.0322(3) 1.05408(15) 0.0480(7) Uani 1 1 d . . .
C14 C 1.1740(4) -0.1709(3) 1.0493(2) 0.0603(8) Uani 1 1 d . . .
H14A H 1.1040 -0.2118 1.0087 0.090 Uiso 1 1 calc R . .
H14B H 1.1538 -0.2099 1.1008 0.090 Uiso 1 1 calc R . .
H14C H 1.2968 -0.1775 1.0354 0.090 Uiso 1 1 calc R . .
C15 C 0.9492(4) -0.0241(4) 1.10241(18) 0.0701(10) Uani 1 1 d . . .
H15A H 0.9032 0.0592 1.0993 0.105 Uiso 1 1 calc R . .
H15B H 0.9719 -0.0450 1.1579 0.105 Uiso 1 1 calc R . .
H15C H 0.8645 -0.0815 1.0803 0.105 Uiso 1 1 calc R . .


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 1.430(3) . ?
O1 H1 0.8400 . ?
O2 C8 1.213(3) . ?
C1 C2 1.507(4) . ?
C1 C6 1.513(4) . ?
C1 H1A 0.9800 . ?
C2 C3 1.351(3) . ?
C2 C7 1.515(4) . ?
C3 C8 1.474(4) . ?
C3 C4 1.534(3) . ?
C4 C9 1.541(4) . ?
C4 C5 1.547(3) . ?
C4 C10 1.553(3) . ?
C5 C6 1.527(3) . ?
C5 C13 1.555(3) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.523(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.517(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.530(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C15 1.530(4) . ?
C13 C14 1.541(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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 H1 109.5 . . ?
O1 C1 C2 110.7(2) . . ?
O1 C1 C6 108.3(2) . . ?
C2 C1 C6 113.9(2) . . ?
O1 C1 H1A 107.9 . . ?
C2 C1 H1A 107.9 . . ?
C6 C1 H1A 107.9 . . ?
C3 C2 C1 122.3(2) . . ?
C3 C2 C7 125.2(2) . . ?
C1 C2 C7 112.5(2) . . ?
C2 C3 C8 117.3(2) . . ?
C2 C3 C4 123.4(2) . . ?
C8 C3 C4 119.1(2) . . ?
C3 C4 C9 107.82(19) . . ?
C3 C4 C5 107.43(18) . . ?
C9 C4 C5 114.7(2) . . ?
C3 C4 C10 109.7(2) . . ?
C9 C4 C10 110.3(2) . . ?
C5 C4 C10 106.83(19) . . ?
C6 C5 C4 109.69(18) . . ?
C6 C5 C13 114.8(2) . . ?
C4 C5 C13 117.5(2) . . ?
C6 C5 H5 104.5 . . ?
C4 C5 H5 104.5 . . ?
C13 C5 H5 104.5 . . ?
C1 C6 C5 108.9(2) . . ?
C1 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
C1 C6 H6B 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 C3 126.1(3) . . ?
O2 C8 H8 117.0 . . ?
C3 C8 H8 117.0 . . ?
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 . . ?
C11 C10 C4 112.2(2) . . ?
C11 C10 H10A 109.2 . . ?
C4 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C4 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C10 111.7(2) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 113.6(2) . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 C15 107.9(2) . . ?
C12 C13 C14 110.6(2) . . ?
C15 C13 C14 107.5(3) . . ?
C12 C13 C5 107.9(2) . . ?
C15 C13 C5 108.8(2) . . ?
C14 C13 C5 113.9(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O1 C1 C2 C3 -132.0(2) . . . . ?
C6 C1 C2 C3 -9.6(4) . . . . ?
O1 C1 C2 C7 48.7(3) . . . . ?
C6 C1 C2 C7 171.1(2) . . . . ?
C1 C2 C3 C8 175.1(2) . . . . ?
C7 C2 C3 C8 -5.7(4) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C7 C2 C3 C4 179.0(2) . . . . ?
C2 C3 C4 C9 101.4(3) . . . . ?
C8 C3 C4 C9 -73.8(3) . . . . ?
C2 C3 C4 C5 -22.7(3) . . . . ?
C8 C3 C4 C5 162.1(2) . . . . ?
C2 C3 C4 C10 -138.4(2) . . . . ?
C8 C3 C4 C10 46.3(3) . . . . ?
C3 C4 C5 C6 55.4(3) . . . . ?
C9 C4 C5 C6 -64.4(3) . . . . ?
C10 C4 C5 C6 173.0(2) . . . . ?
C3 C4 C5 C13 -171.2(2) . . . . ?
C9 C4 C5 C13 69.0(3) . . . . ?
C10 C4 C5 C13 -53.6(3) . . . . ?
O1 C1 C6 C5 165.82(19) . . . . ?
C2 C1 C6 C5 42.2(3) . . . . ?
C4 C5 C6 C1 -67.2(3) . . . . ?
C13 C5 C6 C1 158.0(2) . . . . ?
C2 C3 C8 O2 -157.0(3) . . . . ?
C4 C3 C8 O2 18.5(4) . . . . ?
C3 C4 C10 C11 170.4(2) . . . . ?
C9 C4 C10 C11 -71.0(3) . . . . ?
C5 C4 C10 C11 54.3(3) . . . . ?
C4 C10 C11 C12 -58.1(3) . . . . ?
C10 C11 C12 C13 56.7(4) . . . . ?
C11 C12 C13 C15 -168.6(3) . . . . ?
C11 C12 C13 C14 74.1(3) . . . . ?
C11 C12 C13 C5 -51.1(3) . . . . ?
C6 C5 C13 C12 -176.7(2) . . . . ?
C4 C5 C13 C12 52.1(3) . . . . ?
C6 C5 C13 C15 -59.9(3) . . . . ?
C4 C5 C13 C15 169.0(2) . . . . ?
C6 C5 C13 C14 60.0(3) . . . . ?
C4 C5 C13 C14 -71.1(3) . . . . ?

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 2.13 2.926(3) 158.6 1_455

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        64.98
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_10
_audit_block_doi                 10.5517/cc131xln
_database_code_depnum_ccdc_archive 'CCDC 1014741'
_audit_update_record             
;
2014-12-04 deposited with the CCDC.
2015-02-03 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
_chemical_absolute_configuration unk

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   7.3041(2)
_cell_length_b                   11.6752(3)
_cell_length_c                   15.6101(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1331.18(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2488
_cell_measurement_theta_min      6.69
_cell_measurement_theta_max      68.49

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_type   none

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5449
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         6.69
_diffrn_reflns_theta_max         64.93
_reflns_number_total             1292
_reflns_number_gt                1033
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0629P)²] 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_abs_structure_details '879 Friedel pairs merged'
_refine_ls_number_reflns         1292
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      0.961
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

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 0.8086(4) 0.72411(16) 0.26720(13) 0.0711(7) Uani 1 1 d . . .
O2 O 1.1017(4) 0.74134(17) 0.22811(14) 0.0797(7) Uani 1 1 d . . .
O3 O 0.8528(3) 0.89190(18) 0.66055(12) 0.0672(6) Uani 1 1 d . . .
H3 H 0.7901 0.8634 0.7003 0.101 Uiso 1 1 calc R . .
C1 C 0.9767(6) 0.7743(2) 0.27173(18) 0.0606(8) Uani 1 1 d . . .
C2 C 0.9714(4) 0.8652(2) 0.33607(15) 0.0469(7) Uani 1 1 d . . .
C3 C 0.8055(4) 0.86622(19) 0.37126(15) 0.0452(6) Uani 1 1 d . . .
C4 C 0.6903(5) 0.7777(2) 0.3289(2) 0.0641(9) Uani 1 1 d . . .
H4A H 0.6465 0.7222 0.3703 0.077 Uiso 1 1 calc R . .
H4B H 0.5858 0.8126 0.3008 0.077 Uiso 1 1 calc R . .
C5 C 0.7457(3) 0.9475(2) 0.44088(14) 0.0417(6) Uani 1 1 d . . .
C6 C 0.6207(4) 0.8866(2) 0.50591(16) 0.0517(7) Uani 1 1 d . . .
H6A H 0.5048 0.8685 0.4788 0.062 Uiso 1 1 calc R . .
H6B H 0.6774 0.8153 0.5235 0.062 Uiso 1 1 calc R . .
C7 C 0.5863(4) 0.9609(3) 0.58449(18) 0.0583(8) Uani 1 1 d . . .
H7A H 0.5223 1.0300 0.5673 0.070 Uiso 1 1 calc R . .
H7B H 0.5086 0.9197 0.6243 0.070 Uiso 1 1 calc R . .
C8 C 0.7636(4) 0.9933(2) 0.62882(15) 0.0553(7) Uani 1 1 d . . .
H8 H 0.7347 1.0431 0.6775 0.066 Uiso 1 1 calc R . .
C9 C 0.8985(4) 1.0560(2) 0.57004(15) 0.0481(7) Uani 1 1 d . . .
C10 C 0.9257(3) 0.98385(19) 0.48733(14) 0.0398(6) Uani 1 1 d . . .
H10 H 0.9795 0.9117 0.5073 0.048 Uiso 1 1 calc R . .
C11 C 1.0652(4) 1.0315(2) 0.42351(16) 0.0485(6) Uani 1 1 d . . .
H11A H 1.0111 1.0951 0.3925 0.058 Uiso 1 1 calc R . .
H11B H 1.1709 1.0602 0.4545 0.058 Uiso 1 1 calc R . .
C12 C 1.1269(4) 0.9402(2) 0.35994(16) 0.0555(7) Uani 1 1 d . . .
H12A H 1.1755 0.9768 0.3090 0.067 Uiso 1 1 calc R . .
H12B H 1.2235 0.8944 0.3853 0.067 Uiso 1 1 calc R . .
C13 C 0.6390(4) 1.0446(2) 0.39570(16) 0.0540(7) Uani 1 1 d . . .
H13A H 0.7234 1.0934 0.3659 0.081 Uiso 1 1 calc R . .
H13B H 0.5733 1.0886 0.4376 0.081 Uiso 1 1 calc R . .
H13C H 0.5541 1.0120 0.3556 0.081 Uiso 1 1 calc R . .
C14 C 1.0830(4) 1.0676(3) 0.61699(17) 0.0671(8) Uani 1 1 d . . .
H14A H 1.0624 1.0962 0.6738 0.101 Uiso 1 1 calc R . .
H14B H 1.1604 1.1199 0.5863 0.101 Uiso 1 1 calc R . .
H14C H 1.1413 0.9940 0.6201 0.101 Uiso 1 1 calc R . .
C15 C 0.8277(5) 1.1788(2) 0.5530(2) 0.0672(9) Uani 1 1 d . . .
H15A H 0.7014 1.1757 0.5363 0.101 Uiso 1 1 calc R . .
H15B H 0.8984 1.2131 0.5080 0.101 Uiso 1 1 calc R . .
H15C H 0.8394 1.2237 0.6043 0.101 Uiso 1 1 calc R . .


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 1.362(4) . ?
O1 C4 1.437(4) . ?
O2 C1 1.203(4) . ?
O3 C8 1.439(3) . ?
O3 H3 0.8400 . ?
C1 C2 1.462(4) . ?
C2 C3 1.331(4) . ?
C2 C12 1.482(4) . ?
C3 C4 1.488(4) . ?
C3 C5 1.507(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.539(3) . ?
C5 C13 1.546(3) . ?
C5 C10 1.560(3) . ?
C6 C7 1.523(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.516(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.533(4) . ?
C8 H8 0.9800 . ?
C9 C14 1.540(4) . ?
C9 C15 1.546(4) . ?
C9 C10 1.554(3) . ?
C10 C11 1.530(3) . ?
C10 H10 0.9800 . ?
C11 C12 1.524(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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 C4 108.6(2) . . ?
C8 O3 H3 109.5 . . ?
O2 C1 O1 121.1(3) . . ?
O2 C1 C2 129.9(3) . . ?
O1 C1 C2 108.9(3) . . ?
C3 C2 C1 108.3(3) . . ?
C3 C2 C12 126.1(2) . . ?
C1 C2 C12 125.6(3) . . ?
C2 C3 C4 109.0(2) . . ?
C2 C3 C5 124.5(2) . . ?
C4 C3 C5 126.5(3) . . ?
O1 C4 C3 105.1(3) . . ?
O1 C4 H4A 110.7 . . ?
C3 C4 H4A 110.7 . . ?
O1 C4 H4B 110.7 . . ?
C3 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
C3 C5 C6 110.9(2) . . ?
C3 C5 C13 106.18(19) . . ?
C6 C5 C13 109.9(2) . . ?
C3 C5 C10 105.2(2) . . ?
C6 C5 C10 108.59(19) . . ?
C13 C5 C10 115.9(2) . . ?
C7 C6 C5 111.5(2) . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 111.6(2) . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
O3 C8 C7 109.8(2) . . ?
O3 C8 C9 107.9(2) . . ?
C7 C8 C9 113.3(2) . . ?
O3 C8 H8 108.6 . . ?
C7 C8 H8 108.6 . . ?
C9 C8 H8 108.6 . . ?
C8 C9 C14 108.7(2) . . ?
C8 C9 C15 109.3(2) . . ?
C14 C9 C15 107.0(2) . . ?
C8 C9 C10 108.7(2) . . ?
C14 C9 C10 109.4(2) . . ?
C15 C9 C10 113.7(2) . . ?
C11 C10 C9 115.4(2) . . ?
C11 C10 C5 110.96(19) . . ?
C9 C10 C5 115.2(2) . . ?
C11 C10 H10 104.6 . . ?
C9 C10 H10 104.6 . . ?
C5 C10 H10 104.6 . . ?
C12 C11 C10 111.5(2) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C2 C12 C11 110.5(2) . . ?
C2 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C4 O1 C1 O2 177.4(2) . . . . ?
C4 O1 C1 C2 -1.3(3) . . . . ?
O2 C1 C2 C3 -176.4(3) . . . . ?
O1 C1 C2 C3 2.2(3) . . . . ?
O2 C1 C2 C12 1.5(4) . . . . ?
O1 C1 C2 C12 -179.9(2) . . . . ?
C1 C2 C3 C4 -2.1(3) . . . . ?
C12 C2 C3 C4 180.0(2) . . . . ?
C1 C2 C3 C5 179.7(2) . . . . ?
C12 C2 C3 C5 1.8(4) . . . . ?
C1 O1 C4 C3 0.1(3) . . . . ?
C2 C3 C4 O1 1.3(3) . . . . ?
C5 C3 C4 O1 179.5(2) . . . . ?
C2 C3 C5 C6 -142.0(2) . . . . ?
C4 C3 C5 C6 40.1(3) . . . . ?
C2 C3 C5 C13 98.7(3) . . . . ?
C4 C3 C5 C13 -79.2(3) . . . . ?
C2 C3 C5 C10 -24.8(3) . . . . ?
C4 C3 C5 C10 157.3(2) . . . . ?
C3 C5 C6 C7 170.1(2) . . . . ?
C13 C5 C6 C7 -72.8(3) . . . . ?
C10 C5 C6 C7 54.9(3) . . . . ?
C5 C6 C7 C8 -58.2(3) . . . . ?
C6 C7 C8 O3 -63.5(3) . . . . ?
C6 C7 C8 C9 57.3(3) . . . . ?
O3 C8 C9 C14 -49.5(3) . . . . ?
C7 C8 C9 C14 -171.2(2) . . . . ?
O3 C8 C9 C15 -165.9(2) . . . . ?
C7 C8 C9 C15 72.3(3) . . . . ?
O3 C8 C9 C10 69.5(3) . . . . ?
C7 C8 C9 C10 -52.3(3) . . . . ?
C8 C9 C10 C11 -176.8(2) . . . . ?
C14 C9 C10 C11 -58.4(3) . . . . ?
C15 C9 C10 C11 61.2(3) . . . . ?
C8 C9 C10 C5 51.8(3) . . . . ?
C14 C9 C10 C5 170.3(2) . . . . ?
C15 C9 C10 C5 -70.2(3) . . . . ?
C3 C5 C10 C11 54.2(2) . . . . ?
C6 C5 C10 C11 173.0(2) . . . . ?
C13 C5 C10 C11 -62.8(3) . . . . ?
C3 C5 C10 C9 -172.36(18) . . . . ?
C6 C5 C10 C9 -53.6(3) . . . . ?
C13 C5 C10 C9 70.7(3) . . . . ?
C9 C10 C11 C12 162.2(2) . . . . ?
C5 C10 C11 C12 -64.4(3) . . . . ?
C3 C2 C12 C11 -7.5(3) . . . . ?
C1 C2 C12 C11 175.0(2) . . . . ?
C10 C11 C12 C2 37.6(3) . . . . ?

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 H3 O2 0.84 2.15 2.967(3) 163.1 4_466

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        64.93
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_1
_audit_block_doi                 10.5517/cc131xxz
_database_code_depnum_ccdc_archive 'CCDC 1014751'
_audit_update_record             
;
2014-12-04 deposited with the CCDC.
2015-02-03 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
_chemical_absolute_configuration unk

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0000 '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 0.0492 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   8.064(1)
_cell_length_b                   11.542(1)
_cell_length_c                   14.904(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1387.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    295
_cell_measurement_reflns_used    2577
_cell_measurement_theta_min      4.85
_cell_measurement_theta_max      67.58

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_type   none

_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4997
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.85
_diffrn_reflns_theta_max         64.99
_reflns_number_total             1347
_reflns_number_gt                1284
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?


_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)+(0.0735P)²+0.1316P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0042(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details '861 Friedel pairs merged'
_refine_ls_number_reflns         1347
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.1067
_refine_ls_wR_factor_gt          0.1050
_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         0.001

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 0.7682(2) 1.01121(15) 0.64620(11) 0.0580(5) Uani 1 1 d . . .
O2 O 0.5737(3) 1.14445(19) 0.66969(16) 0.0808(7) Uani 1 1 d . . .
O3 O 0.7633(2) 0.70447(13) 0.82306(14) 0.0634(5) Uani 1 1 d . . .
H3 H 0.6621 0.6877 0.8198 0.095 Uiso 1 1 calc R . .
C1 C 0.6449(3) 1.0580(2) 0.69489(18) 0.0570(6) Uani 1 1 d . . .
C2 C 0.6208(3) 0.9896(2) 0.77757(18) 0.0520(6) Uani 1 1 d . . .
C3 C 0.7308(2) 0.90400(18) 0.77699(15) 0.0441(5) Uani 1 1 d . . .
C4 C 0.8319(3) 0.90875(19) 0.69269(15) 0.0446(5) Uani 1 1 d . . .
C5 C 0.4968(4) 1.0253(3) 0.8470(2) 0.0782(9) Uani 1 1 d . . .
H5A H 0.4967 0.9687 0.8960 0.117 Uiso 1 1 calc R . .
H5B H 0.3862 1.0286 0.8198 0.117 Uiso 1 1 calc R . .
H5C H 0.5263 1.1018 0.8705 0.117 Uiso 1 1 calc R . .
C6 C 0.7810(3) 0.82252(18) 0.85036(16) 0.0461(5) Uani 1 1 d . . .
H6A H 0.7116 0.8371 0.9048 0.055 Uiso 1 1 calc R . .
C7 C 0.9649(3) 0.84530(19) 0.87263(15) 0.0462(5) Uani 1 1 d . . .
C8 C 1.0678(2) 0.83763(18) 0.78589(15) 0.0452(5) Uani 1 1 d . . .
H8A H 1.1858 0.8510 0.8011 0.054 Uiso 1 1 calc R . .
H8B H 1.0585 0.7580 0.7618 0.054 Uiso 1 1 calc R . .
C9 C 1.0176(2) 0.92323(16) 0.71189(15) 0.0408(5) Uani 1 1 d . . .
H9A H 1.0415 1.0045 0.7313 0.049 Uiso 1 1 calc R . .
C10 C 1.0973(3) 0.8995(2) 0.61916(16) 0.0520(6) Uani 1 1 d . . .
H10A H 1.0771 0.9691 0.5807 0.062 Uiso 1 1 calc R . .
C11 C 0.9936(4) 0.8006(2) 0.58152(19) 0.0711(8) Uani 1 1 d . . .
H11A H 0.9816 0.8089 0.5157 0.085 Uiso 1 1 calc R . .
H11B H 1.0477 0.7253 0.5942 0.085 Uiso 1 1 calc R . .
C12 C 0.8240(4) 0.8060(2) 0.62679(18) 0.0627(7) Uani 1 1 d . . .
H12A H 0.8009 0.7330 0.6593 0.075 Uiso 1 1 calc R . .
H12B H 0.7357 0.8184 0.5817 0.075 Uiso 1 1 calc R . .
C13 C 1.2829(4) 0.8775(3) 0.6203(2) 0.0801(9) Uani 1 1 d . . .
H13A H 1.3219 0.8633 0.5590 0.120 Uiso 1 1 calc R . .
H13B H 1.3067 0.8095 0.6576 0.120 Uiso 1 1 calc R . .
H13C H 1.3400 0.9453 0.6450 0.120 Uiso 1 1 calc R . .
C14 C 1.0267(4) 0.7547(3) 0.93984(17) 0.0668(7) Uani 1 1 d . . .
H14A H 1.1435 0.7695 0.9539 0.100 Uiso 1 1 calc R . .
H14B H 1.0154 0.6772 0.9137 0.100 Uiso 1 1 calc R . .
H14C H 0.9607 0.7595 0.9949 0.100 Uiso 1 1 calc R . .
C15 C 0.9804(4) 0.9662(2) 0.91564(18) 0.0640(7) Uani 1 1 d . . .
H15A H 1.0969 0.9816 0.9301 0.096 Uiso 1 1 calc R . .
H15B H 0.9140 0.9690 0.9707 0.096 Uiso 1 1 calc R . .
H15C H 0.9402 1.0250 0.8735 0.096 Uiso 1 1 calc R . .


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 1.344(3) . ?
O1 C4 1.464(3) . ?
O2 C1 1.211(3) . ?
O3 C6 1.429(3) . ?
O3 H3 0.8400 . ?
C1 C2 1.476(4) . ?
C2 C3 1.328(3) . ?
C2 C5 1.496(4) . ?
C3 C6 1.498(3) . ?
C3 C4 1.499(3) . ?
C4 C9 1.534(3) . ?
C4 C12 1.541(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.542(3) . ?
C6 H6A 1.0000 . ?
C7 C14 1.531(3) . ?
C7 C8 1.539(3) . ?
C7 C15 1.541(3) . ?
C8 C9 1.535(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.549(3) . ?
C9 H9A 1.0000 . ?
C10 C13 1.518(4) . ?
C10 C11 1.522(4) . ?
C10 H10A 1.0000 . ?
C11 C12 1.526(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
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
C1 O1 C4 109.18(18) . . ?
C6 O3 H3 109.5 . . ?
O2 C1 O1 120.9(2) . . ?
O2 C1 C2 129.6(3) . . ?
O1 C1 C2 109.5(2) . . ?
C3 C2 C1 107.7(2) . . ?
C3 C2 C5 131.0(2) . . ?
C1 C2 C5 121.2(2) . . ?
C2 C3 C6 130.0(2) . . ?
C2 C3 C4 110.0(2) . . ?
C6 C3 C4 119.21(18) . . ?
O1 C4 C3 103.62(17) . . ?
O1 C4 C9 110.06(17) . . ?
C3 C4 C9 112.25(18) . . ?
O1 C4 C12 107.80(19) . . ?
C3 C4 C12 118.93(19) . . ?
C9 C4 C12 104.06(18) . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O3 C6 C3 111.32(19) . . ?
O3 C6 C7 108.67(18) . . ?
C3 C6 C7 108.05(17) . . ?
O3 C6 H6A 109.6 . . ?
C3 C6 H6A 109.6 . . ?
C7 C6 H6A 109.6 . . ?
C14 C7 C8 109.57(19) . . ?
C14 C7 C15 108.7(2) . . ?
C8 C7 C15 110.97(19) . . ?
C14 C7 C6 109.7(2) . . ?
C8 C7 C6 109.15(18) . . ?
C15 C7 C6 108.77(19) . . ?
C9 C8 C7 115.10(17) . . ?
C9 C8 H8A 108.5 . . ?
C7 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C8 C9 C4 108.76(17) . . ?
C8 C9 C10 114.69(17) . . ?
C4 C9 C10 102.68(19) . . ?
C8 C9 H9A 110.1 . . ?
C4 C9 H9A 110.1 . . ?
C10 C9 H9A 110.1 . . ?
C13 C10 C11 114.8(2) . . ?
C13 C10 C9 115.4(2) . . ?
C11 C10 C9 103.50(19) . . ?
C13 C10 H10A 107.6 . . ?
C11 C10 H10A 107.6 . . ?
C9 C10 H10A 107.6 . . ?
C12 C11 C10 107.4(2) . . ?
C12 C11 H11A 110.2 . . ?
C10 C11 H11A 110.2 . . ?
C12 C11 H11B 110.2 . . ?
C10 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C11 C12 C4 106.0(2) . . ?
C11 C12 H12A 110.5 . . ?
C4 C12 H12A 110.5 . . ?
C11 C12 H12B 110.5 . . ?
C4 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C4 O1 C1 O2 179.6(2) . . . . ?
C4 O1 C1 C2 0.7(3) . . . . ?
O2 C1 C2 C3 -178.3(3) . . . . ?
O1 C1 C2 C3 0.5(3) . . . . ?
O2 C1 C2 C5 -1.8(4) . . . . ?
O1 C1 C2 C5 176.9(2) . . . . ?
C1 C2 C3 C6 168.0(2) . . . . ?
C5 C2 C3 C6 -8.0(4) . . . . ?
C1 C2 C3 C4 -1.4(2) . . . . ?
C5 C2 C3 C4 -177.4(3) . . . . ?
C1 O1 C4 C3 -1.4(2) . . . . ?
C1 O1 C4 C9 -121.6(2) . . . . ?
C1 O1 C4 C12 125.5(2) . . . . ?
C2 C3 C4 O1 1.7(2) . . . . ?
C6 C3 C4 O1 -168.99(18) . . . . ?
C2 C3 C4 C9 120.4(2) . . . . ?
C6 C3 C4 C9 -50.3(3) . . . . ?
C2 C3 C4 C12 -117.8(2) . . . . ?
C6 C3 C4 C12 71.5(3) . . . . ?
C2 C3 C6 O3 125.1(2) . . . . ?
C4 C3 C6 O3 -66.3(3) . . . . ?
C2 C3 C6 C7 -115.6(2) . . . . ?
C4 C3 C6 C7 53.0(3) . . . . ?
O3 C6 C7 C14 -52.7(2) . . . . ?
C3 C6 C7 C14 -173.65(19) . . . . ?
O3 C6 C7 C8 67.3(2) . . . . ?
C3 C6 C7 C8 -53.6(2) . . . . ?
O3 C6 C7 C15 -171.47(18) . . . . ?
C3 C6 C7 C15 67.6(2) . . . . ?
C14 C7 C8 C9 179.4(2) . . . . ?
C15 C7 C8 C9 -60.6(3) . . . . ?
C6 C7 C8 C9 59.2(2) . . . . ?
C7 C8 C9 C4 -54.3(2) . . . . ?
C7 C8 C9 C10 -168.62(18) . . . . ?
O1 C4 C9 C8 161.28(17) . . . . ?
C3 C4 C9 C8 46.4(2) . . . . ?
C12 C4 C9 C8 -83.5(2) . . . . ?
O1 C4 C9 C10 -76.8(2) . . . . ?
C3 C4 C9 C10 168.34(17) . . . . ?
C12 C4 C9 C10 38.5(2) . . . . ?
C8 C9 C10 C13 -47.4(3) . . . . ?
C4 C9 C10 C13 -165.2(2) . . . . ?
C8 C9 C10 C11 78.9(3) . . . . ?
C4 C9 C10 C11 -38.9(2) . . . . ?
C13 C10 C11 C12 151.3(3) . . . . ?
C9 C10 C11 C12 24.6(3) . . . . ?
C10 C11 C12 C4 -0.9(3) . . . . ?
O1 C4 C12 C11 93.4(2) . . . . ?
C3 C4 C12 C11 -149.2(2) . . . . ?
C9 C4 C12 C11 -23.5(3) . . . . ?

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 H3 O2 0.84 1.97 2.806(3) 172.1 3_646

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        64.99
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.027
