# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

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

data_1979GuillotICMMO
_audit_block_doi                 10.5517/cc12lvvc
_database_code_depnum_ccdc_archive 'CCDC 1001233'
_audit_update_record             
;
2016-06-03 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H18 O3'
_chemical_formula_sum            'C12 H18 O3'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         210.26

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3024(6)
_cell_length_b                   8.6519(8)
_cell_length_c                   8.9513(6)
_cell_angle_alpha                77.266(2)
_cell_angle_beta                 86.338(2)
_cell_angle_gamma                88.215(2)
_cell_volume                     550.42(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    1461
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      29.85
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_F_000             228
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9912
_exptl_absorpt_correction_T_max  0.9981
_exptl_absorpt_process_details   SADABS
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'kappa X8 APEX II Bruker ICMMO'
_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            5638
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.337
_diffrn_reflns_theta_max         30.490
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.713
_diffrn_measured_fraction_theta_full 0.910
_reflns_number_total             2395
_reflns_number_gt                1751
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0550P)²+0.1099P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2395
_refine_ls_number_parameters     140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.1016
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6791(2) 0.83865(18) 0.6273(2) 0.0263(4) Uani 1 1 d . . . . .
H1A H 0.7449 0.8521 0.5291 0.039 Uiso 1 1 calc R U . . .
H1B H 0.5545 0.8752 0.6135 0.039 Uiso 1 1 calc R U . . .
H1C H 0.6803 0.7285 0.6776 0.039 Uiso 1 1 calc R U . . .
C2 C 0.7694(2) 0.93319(16) 0.72442(18) 0.0197(4) Uani 1 1 d . . . . .
H2 H 0.6971 0.9230 0.8220 0.024 Uiso 1 1 calc R U . . .
C3 C 0.7907(2) 1.10710(16) 0.65221(18) 0.0193(3) Uani 1 1 d . . . . .
H3A H 0.6709 1.1561 0.6319 0.023 Uiso 1 1 calc R U . . .
H3B H 0.8624 1.1195 0.5554 0.023 Uiso 1 1 calc R U . . .
C4 C 0.8858(2) 1.18734(15) 0.75965(18) 0.0167(3) Uani 1 1 d . . . . .
H4 H 0.8089 1.1746 0.8553 0.020 Uiso 1 1 calc R U . . .
C5 C 1.0681(2) 1.10278(15) 0.79736(17) 0.0157(3) Uani 1 1 d . . . . .
C6 C 1.0880(2) 0.93457(16) 0.79630(18) 0.0180(3) Uani 1 1 d . . . . .
C7 C 0.9140(2) 1.36347(16) 0.6976(2) 0.0223(4) Uani 1 1 d . . . . .
H7A H 0.7960 1.4185 0.6908 0.027 Uiso 1 1 calc R U . . .
H7B H 0.9733 1.3808 0.5954 0.027 Uiso 1 1 calc R U . . .
C8 C 1.0317(2) 1.42910(16) 0.8022(2) 0.0224(4) Uani 1 1 d . . . . .
H8A H 0.9735 1.4078 0.9049 0.027 Uiso 1 1 calc R U . . .
H8B H 1.0388 1.5432 0.7663 0.027 Uiso 1 1 calc R U . . .
C9 C 1.2268(2) 1.35770(15) 0.80854(18) 0.0180(3) Uani 1 1 d . . . . .
C10 C 1.2196(2) 1.18002(16) 0.82182(17) 0.0167(3) Uani 1 1 d . . . . .
C11 C 1.3184(2) 1.39489(18) 0.9447(2) 0.0265(4) Uani 1 1 d . . . . .
H11A H 1.2490 1.3496 1.0379 0.040 Uiso 1 1 calc R U . . .
H11B H 1.3233 1.5077 0.9334 0.040 Uiso 1 1 calc R U . . .
H11C H 1.4408 1.3508 0.9485 0.040 Uiso 1 1 calc R U . . .
C12 C 1.3428(2) 1.42882(17) 0.66097(19) 0.0244(4) Uani 1 1 d . . . . .
H12A H 1.4636 1.3817 0.6663 0.037 Uiso 1 1 calc R U . . .
H12B H 1.3512 1.5412 0.6507 0.037 Uiso 1 1 calc R U . . .
H12C H 1.2858 1.4079 0.5739 0.037 Uiso 1 1 calc R U . . .
O1 O 0.95003(15) 0.85687(11) 0.75517(13) 0.0213(3) Uani 1 1 d . . . . .
O2 O 1.23051(15) 0.85605(11) 0.82722(13) 0.0241(3) Uani 1 1 d . . . . .
O3 O 1.38091(14) 1.10612(11) 0.85437(13) 0.0229(3) Uani 1 1 d . . . . .
H3 H 1.3728 1.0121 0.8533 0.034 Uiso 1 1 calc R U . . .


_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 C2 1.510(2) . ?
C2 O1 1.4707(17) . ?
C2 C3 1.5095(18) . ?
C3 C4 1.516(2) . ?
C4 C7 1.5182(18) . ?
C4 C5 1.520(2) . ?
C5 C10 1.364(2) . ?
C5 C6 1.4601(19) . ?
C6 O2 1.2372(17) . ?
C6 O1 1.3422(18) . ?
C7 C8 1.518(2) . ?
C8 C9 1.534(2) . ?
C9 C10 1.5178(18) . ?
C9 C11 1.526(2) . ?
C9 C12 1.540(2) . ?
C10 O3 1.3405(17) . ?

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 C2 C3 110.42(11) . . ?
O1 C2 C1 105.61(12) . . ?
C3 C2 C1 114.89(13) . . ?
C2 C3 C4 109.59(12) . . ?
C3 C4 C7 113.84(12) . . ?
C3 C4 C5 108.93(12) . . ?
C7 C4 C5 110.54(12) . . ?
C10 C5 C6 117.87(13) . . ?
C10 C5 C4 122.62(12) . . ?
C6 C5 C4 119.35(13) . . ?
O2 C6 O1 115.79(12) . . ?
O2 C6 C5 123.69(14) . . ?
O1 C6 C5 120.49(13) . . ?
C4 C7 C8 110.15(12) . . ?
C7 C8 C9 112.84(13) . . ?
C10 C9 C11 110.77(12) . . ?
C10 C9 C8 109.81(11) . . ?
C11 C9 C8 109.39(13) . . ?
C10 C9 C12 107.80(12) . . ?
C11 C9 C12 108.43(13) . . ?
C8 C9 C12 110.63(12) . . ?
O3 C10 C5 122.85(12) . . ?
O3 C10 C9 112.92(12) . . ?
C5 C10 C9 124.18(13) . . ?
C6 O1 C2 121.42(11) . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration .

####################################################################### 
# 
# 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_17
_database_code_depnum_ccdc_archive 'CCDC 1497250'
_audit_update_record             
;
2016-08-02 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H22 O3'
_chemical_formula_sum            'C14 H22 O3'
_chemical_formula_weight         238.31

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.704(2)
_cell_length_b                   6.297(3)
_cell_length_c                   18.887(9)
_cell_angle_alpha                93.901(11)
_cell_angle_beta                 95.455(10)
_cell_angle_gamma                106.130(10)
_cell_volume                     645.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    1244
_cell_measurement_theta_min      3.38
_cell_measurement_theta_max      30.06

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_F_000             260
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9825
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_process_details   SADABS
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source_type              'kappa X8 APEX II Bruker ICMMO'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9528
_diffrn_reflns_av_unetI/netI     0.1037
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.177
_diffrn_reflns_theta_max         30.517
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             3599
_reflns_number_gt                1969
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1279P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3599
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.0788
_refine_ls_wR_factor_ref         0.2402
_refine_ls_wR_factor_gt          0.1943
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5497(4) 1.2783(4) 0.36417(13) 0.0203(5) Uani 1 1 d . . . . .
C2 C 0.7020(4) 1.2141(4) 0.30877(13) 0.0199(5) Uani 1 1 d . . . . .
H2A H 0.7613 1.0923 0.3239 0.024 Uiso 1 1 calc R U . . .
H2B H 0.8436 1.3393 0.3053 0.024 Uiso 1 1 calc R U . . .
C3 C 0.5507(4) 1.1449(4) 0.23565(13) 0.0176(5) Uani 1 1 d . . . . .
H3 H 0.5000 1.2726 0.2202 0.021 Uiso 1 1 calc R U . . .
C4 C 0.6889(4) 1.0700(4) 0.17837(13) 0.0203(5) Uani 1 1 d . . . . .
H4A H 0.7500 0.9491 0.1936 0.024 Uiso 1 1 calc R U . . .
H4B H 0.8281 1.1920 0.1706 0.024 Uiso 1 1 calc R U . . .
C5 C 0.5141(4) 0.9931(4) 0.10929(13) 0.0209(5) Uani 1 1 d . . . . .
H5A H 0.6051 0.9571 0.0716 0.025 Uiso 1 1 calc R U . . .
H5B H 0.4506 1.1141 0.0956 0.025 Uiso 1 1 calc R U . . .
C6 C 0.2972(4) 0.7892(4) 0.11608(13) 0.0197(5) Uani 1 1 d . . . . .
C7 C 0.2103(4) 0.8016(4) 0.18885(13) 0.0170(5) Uani 1 1 d . . . . .
C8 C 0.3223(4) 0.9615(4) 0.24344(12) 0.0157(5) Uani 1 1 d . . . . .
C9 C 0.2245(4) 0.9436(4) 0.31190(13) 0.0179(5) Uani 1 1 d . . . . .
C10 C 0.0824(5) 0.7793(5) 0.05897(14) 0.0267(6) Uani 1 1 d . . . . .
H10A H -0.0511 0.6497 0.0624 0.040 Uiso 1 1 calc R U . . .
H10B H 0.1356 0.7724 0.0124 0.040 Uiso 1 1 calc R U . . .
H10C H 0.0286 0.9098 0.0665 0.040 Uiso 1 1 calc R U . . .
C11 C 0.3738(5) 0.5742(4) 0.10576(14) 0.0241(6) Uani 1 1 d . . . . .
H11A H 0.5153 0.5837 0.1390 0.036 Uiso 1 1 calc R U . . .
H11B H 0.4130 0.5550 0.0579 0.036 Uiso 1 1 calc R U . . .
H11C H 0.2409 0.4497 0.1140 0.036 Uiso 1 1 calc R U . . .
C12 C 0.4526(5) 1.4738(4) 0.34713(14) 0.0251(6) Uani 1 1 d . . . . .
H12A H 0.3449 1.4357 0.3030 0.038 Uiso 1 1 calc R U . . .
H12B H 0.5878 1.6009 0.3426 0.038 Uiso 1 1 calc R U . . .
H12C H 0.3637 1.5078 0.3850 0.038 Uiso 1 1 calc R U . . .
C13 C 0.6860(5) 1.3227(5) 0.43957(14) 0.0257(6) Uani 1 1 d . . . . .
H13A H 0.5734 1.3451 0.4728 0.031 Uiso 1 1 calc R U . . .
H13B H 0.8180 1.4598 0.4424 0.031 Uiso 1 1 calc R U . . .
C14 C 0.7952(5) 1.1395(5) 0.46390(15) 0.0296(6) Uani 1 1 d . . . . .
H14A H 0.6756 0.9974 0.4516 0.044 Uiso 1 1 calc R U . . .
H14B H 0.8398 1.1627 0.5147 0.044 Uiso 1 1 calc R U . . .
H14C H 0.9385 1.1435 0.4406 0.044 Uiso 1 1 calc R U . . .
O1 O 0.0112(3) 0.6339(3) 0.19546(9) 0.0223(4) Uani 1 1 d . . . . .
H1 H -0.0351 0.6519 0.2346 0.034 Uiso 1 1 calc R U . . .
O2 O 0.0377(3) 0.7943(3) 0.32123(9) 0.0221(4) Uani 1 1 d . . . . .
O3 O 0.3329(3) 1.0857(3) 0.36847(9) 0.0205(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O3 1.485(3) . ?
C1 C2 1.524(3) . ?
C1 C12 1.525(4) . ?
C1 C13 1.525(4) . ?
C2 C3 1.525(3) . ?
C3 C8 1.509(3) . ?
C3 C4 1.521(3) . ?
C4 C5 1.526(3) . ?
C5 C6 1.538(3) . ?
C6 C7 1.509(3) . ?
C6 C10 1.538(3) . ?
C6 C11 1.540(4) . ?
C7 O1 1.341(3) . ?
C7 C8 1.364(3) . ?
C8 C9 1.455(3) . ?
C9 O2 1.246(3) . ?
C9 O3 1.327(3) . ?
C13 C14 1.532(4) . ?

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
O3 C1 C2 108.80(19) . . ?
O3 C1 C12 107.05(18) . . ?
C2 C1 C12 114.2(2) . . ?
O3 C1 C13 104.03(19) . . ?
C2 C1 C13 112.5(2) . . ?
C12 C1 C13 109.7(2) . . ?
C1 C2 C3 111.15(19) . . ?
C8 C3 C4 110.0(2) . . ?
C8 C3 C2 108.42(19) . . ?
C4 C3 C2 113.9(2) . . ?
C3 C4 C5 108.78(19) . . ?
C4 C5 C6 112.9(2) . . ?
C7 C6 C5 110.9(2) . . ?
C7 C6 C10 108.6(2) . . ?
C5 C6 C10 109.6(2) . . ?
C7 C6 C11 108.2(2) . . ?
C5 C6 C11 110.51(19) . . ?
C10 C6 C11 109.0(2) . . ?
O1 C7 C8 122.6(2) . . ?
O1 C7 C6 112.8(2) . . ?
C8 C7 C6 124.6(2) . . ?
C7 C8 C9 118.1(2) . . ?
C7 C8 C3 121.8(2) . . ?
C9 C8 C3 120.0(2) . . ?
O2 C9 O3 116.2(2) . . ?
O2 C9 C8 122.5(2) . . ?
O3 C9 C8 121.3(2) . . ?
C1 C13 C14 115.4(2) . . ?
C9 O3 C1 121.95(19) . . ?

_refine_diff_density_max         0.585
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.098

