# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_cu_vmfj229a_0m
_database_code_depnum_ccdc_archive 'CCDC 1508992'
_audit_update_record             
;
2016-10-10 deposited with the CCDC.
2017-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 O'
_chemical_formula_sum            'C10 H10 O'
_chemical_formula_weight         146.18

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_H-M_alt        'R 3 :H'
_space_group_name_Hall           'R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'

_cell_length_a                   19.0072(9)
_cell_length_b                   19.0072(9)
_cell_length_c                   5.7243(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1790.97(19)
_cell_formula_units_Z            9
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5980
_cell_measurement_theta_min      4.65
_cell_measurement_theta_max      70.14

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_F_000             702
_exptl_transmission_factor_min   0.4011
_exptl_transmission_factor_max   0.7533
_exptl_crystal_size_max          1.860
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    0.608
_shelx_estimated_absorpt_T_min   0.398
_shelx_estimated_absorpt_T_max   0.815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4919
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_av_R_equivalents  0.1282
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         4.653
_diffrn_reflns_theta_max         70.960
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_point_group_measured_fraction_full 0.921
_reflns_number_total             1370
_reflns_number_gt                1343
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_max     0.830
_reflns_Friedel_fraction_full    0.868

_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 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1668P)²+0.9200P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.006(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.1(6)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         1370
_refine_ls_number_parameters     102
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0773
_refine_ls_wR_factor_ref         0.2129
_refine_ls_wR_factor_gt          0.2082
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.120
_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
O1 O 0.71533(17) 0.73137(18) 0.0252(6) 0.0159(9) Uani 1 1 d . . . . .
H10 H 0.6780 0.7042 -0.0707 0.024 Uiso 1 1 calc R U . . .
C1 C 0.8783(2) 0.8535(3) 0.2402(8) 0.0207(11) Uani 1 1 d . . . . .
H1 H 0.8900 0.8971 0.3437 0.025 Uiso 1 1 calc R U . . .
C2 C 0.8458(3) 0.8533(3) -0.0002(9) 0.0215(11) Uani 1 1 d . . . . .
H3 H 0.8919 0.8842 -0.1083 0.026 Uiso 1 1 calc R U . . .
H9 H 0.8135 0.8810 0.0057 0.026 Uiso 1 1 calc R U . . .
C3 C 0.7930(3) 0.7675(2) -0.0935(7) 0.0154(10) Uani 1 1 d . . . . .
H8 H 0.7844 0.7698 -0.2651 0.019 Uiso 1 1 calc R U . . .
C4 C 0.8298(2) 0.7142(3) -0.0498(7) 0.0144(10) Uani 1 1 d . . . . .
C5 C 0.8143(2) 0.6510(3) -0.2001(6) 0.0160(11) Uani 1 1 d . . . . .
H5 H 0.7844 0.6438 -0.3396 0.019 Uiso 1 1 calc R U . . .
C6 C 0.8428(2) 0.5977(2) -0.1468(8) 0.0173(10) Uani 1 1 d . . . . .
H2 H 0.8323 0.5545 -0.2502 0.021 Uiso 1 1 calc R U . . .
C7 C 0.8747(2) 0.7258(2) 0.1564(7) 0.0136(10) Uani 1 1 d . . . . .
C8 C 0.8908(3) 0.7940(3) 0.3107(7) 0.0191(11) Uani 1 1 d . . . . .
H4 H 0.9107 0.7957 0.4641 0.023 Uiso 1 1 calc R U . . .
C9 C 0.9021(2) 0.6715(3) 0.2085(7) 0.0163(10) Uani 1 1 d . . . . .
H7 H 0.9318 0.6782 0.3483 0.020 Uiso 1 1 calc R U . . .
C10 C 0.8864(3) 0.6083(3) 0.0584(7) 0.0177(11) Uani 1 1 d . . . . .
H6 H 0.9054 0.5719 0.0952 0.021 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
O1 C3 1.448(5) . ?
O1 H10 0.8400 . ?
C1 C8 1.330(7) . ?
C1 C2 1.507(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.523(6) . ?
C2 H3 0.9900 . ?
C2 H9 0.9900 . ?
C3 C4 1.512(6) . ?
C3 H8 1.0000 . ?
C4 C5 1.384(6) . ?
C4 C7 1.408(5) . ?
C5 C6 1.400(6) . ?
C5 H5 0.9500 . ?
C6 C10 1.394(6) . ?
C6 H2 0.9500 . ?
C7 C9 1.402(6) . ?
C7 C8 1.469(6) . ?
C8 H4 0.9500 . ?
C9 C10 1.383(6) . ?
C9 H7 0.9500 . ?
C10 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H10 109.5 . . ?
C8 C1 C2 121.5(4) . . ?
C8 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C1 C2 C3 111.9(4) . . ?
C1 C2 H3 109.2 . . ?
C3 C2 H3 109.2 . . ?
C1 C2 H9 109.2 . . ?
C3 C2 H9 109.2 . . ?
H3 C2 H9 107.9 . . ?
O1 C3 C4 108.0(3) . . ?
O1 C3 C2 108.3(3) . . ?
C4 C3 C2 112.4(3) . . ?
O1 C3 H8 109.4 . . ?
C4 C3 H8 109.4 . . ?
C2 C3 H8 109.4 . . ?
C5 C4 C7 120.4(4) . . ?
C5 C4 C3 120.6(4) . . ?
C7 C4 C3 118.8(4) . . ?
C4 C5 C6 120.1(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C10 C6 C5 119.8(4) . . ?
C10 C6 H2 120.1 . . ?
C5 C6 H2 120.1 . . ?
C9 C7 C4 118.9(4) . . ?
C9 C7 C8 122.1(4) . . ?
C4 C7 C8 119.0(4) . . ?
C1 C8 C7 121.4(4) . . ?
C1 C8 H4 119.3 . . ?
C7 C8 H4 119.3 . . ?
C10 C9 C7 120.6(4) . . ?
C10 C9 H7 119.7 . . ?
C7 C9 H7 119.7 . . ?
C9 C10 C6 120.2(4) . . ?
C9 C10 H6 119.9 . . ?
C6 C10 H6 119.9 . . ?

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
C8 C1 C2 C3 28.3(6) . . . . ?
C1 C2 C3 O1 75.2(4) . . . . ?
C1 C2 C3 C4 -44.0(4) . . . . ?
O1 C3 C4 C5 89.9(4) . . . . ?
C2 C3 C4 C5 -150.7(4) . . . . ?
O1 C3 C4 C7 -84.9(4) . . . . ?
C2 C3 C4 C7 34.4(5) . . . . ?
C7 C4 C5 C6 0.5(6) . . . . ?
C3 C4 C5 C6 -174.3(4) . . . . ?
C4 C5 C6 C10 0.2(6) . . . . ?
C5 C4 C7 C9 -1.0(6) . . . . ?
C3 C4 C7 C9 173.8(4) . . . . ?
C5 C4 C7 C8 179.3(4) . . . . ?
C3 C4 C7 C8 -5.9(5) . . . . ?
C2 C1 C8 C7 0.8(6) . . . . ?
C9 C7 C8 C1 167.1(4) . . . . ?
C4 C7 C8 C1 -13.2(6) . . . . ?
C4 C7 C9 C10 0.9(6) . . . . ?
C8 C7 C9 C10 -179.4(3) . . . . ?
C7 C9 C10 C6 -0.2(6) . . . . ?
C5 C6 C10 C9 -0.4(6) . . . . ?

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 H10 O1 0.84 1.87 2.708(4) 174.1 8_654
O1 H10 O1 0.84 1.87 2.708(4) 174.1 8_654
O1 H10 O1 0.84 1.87 2.708(4) 174.1 8_654
O1 H10 O1 0.84 1.87 2.708(4) 174.1 8_654
O1 H10 O1 0.84 1.87 2.708(4) 174.1 8_654
O1 H10 O1 0.84 1.87 2.708(4) 174.1 8_654
O1 H10 O1 0.84 1.87 2.708(4) 174.1 8_654
O1 H10 O1 0.84 1.87 2.708(4) 174.1 8_654
O1 H10 O1 0.84 1.87 2.708(4) 174.1 8_654

_refine_diff_density_max         0.436
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.121

####################################################################### 
# 
# 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_cu_vmfj1_0m
_database_code_depnum_ccdc_archive 'CCDC 1526719'
_audit_update_record             
;
2017-01-11 deposited with the CCDC.
2017-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 O2'
_chemical_formula_sum            'C11 H12 O2'
_chemical_formula_weight         176.21

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   4.6462(2)
_cell_length_b                   9.7488(3)
_cell_length_c                   19.6719(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     891.04(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4863
_cell_measurement_theta_min      4.54
_cell_measurement_theta_max      69.80

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   0.5115
_exptl_transmission_factor_max   0.7533
_exptl_crystal_size_max          1.360
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.340
_exptl_absorpt_coefficient_mu    0.720
_shelx_estimated_absorpt_T_min   0.441
_shelx_estimated_absorpt_T_max   0.792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4844
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         5.063
_diffrn_reflns_theta_max         69.794
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             1612
_reflns_number_gt                1609
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.609
_reflns_Friedel_fraction_max     0.916
_reflns_Friedel_fraction_full    0.946

_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 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0956P)²+0.1665P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.046(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 607 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1612
_refine_ls_number_parameters     123
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1385
_refine_ls_wR_factor_gt          0.1384
_refine_ls_goodness_of_fit_ref   1.203
_refine_ls_restrained_S_all      1.203
_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
O1 O 0.2016(4) 0.67288(18) 0.85487(9) 0.0248(5) Uani 1 1 d . . . . .
O2 O 0.5151(4) 0.78838(18) 0.97077(8) 0.0178(5) Uani 1 1 d . . . . .
H9 H 0.342(10) 0.776(3) 0.9821(17) 0.027 Uiso 1 1 d . U . . .
C1 C 0.2299(6) 0.5395(3) 0.88117(14) 0.0256(6) Uani 1 1 d . . . . .
H3 H 0.3836 0.4912 0.8569 0.038 Uiso 1 1 calc R U . . .
H12 H 0.0481 0.4898 0.8753 0.038 Uiso 1 1 calc R U . . .
H1 H 0.2776 0.5445 0.9296 0.038 Uiso 1 1 calc R U . . .
C2 C 0.4643(6) 0.7486(2) 0.84851(12) 0.0172(6) Uani 1 1 d . . . . .
H11 H 0.6311 0.6838 0.8481 0.021 Uiso 1 1 calc R U . . .
C3 C 0.4479(5) 0.8235(3) 0.78130(11) 0.0201(6) Uani 1 1 d . . . . .
H4 H 0.5285 0.7831 0.7417 0.024 Uiso 1 1 calc R U . . .
C4 C 0.3214(6) 0.9454(3) 0.77749(12) 0.0206(6) Uani 1 1 d . . . . .
H5 H 0.3049 0.9888 0.7344 0.025 Uiso 1 1 calc R U . . .
C5 C 0.2067(5) 1.0149(2) 0.83740(12) 0.0159(6) Uani 1 1 d . . . . .
C6 C 0.0152(6) 1.1250(3) 0.83178(14) 0.0219(6) Uani 1 1 d . . . . .
H6 H -0.0369 1.1584 0.7881 0.026 Uiso 1 1 calc R U . . .
C7 C -0.0992(6) 1.1859(3) 0.88951(15) 0.0243(6) Uani 1 1 d . . . . .
H2 H -0.2317 1.2596 0.8853 0.029 Uiso 1 1 calc R U . . .
C8 C 0.2857(5) 0.9677(2) 0.90228(11) 0.0133(5) Uani 1 1 d . . . . .
C9 C 0.1735(5) 1.0302(2) 0.95961(12) 0.0180(6) Uani 1 1 d . . . . .
H8 H 0.2286 0.9990 1.0035 0.022 Uiso 1 1 calc R U . . .
C10 C -0.0198(6) 1.1388(2) 0.95334(14) 0.0224(6) Uani 1 1 d . . . . .
H7 H -0.0973 1.1808 0.9929 0.027 Uiso 1 1 calc R U . . .
C11 C 0.5026(5) 0.8528(2) 0.90590(11) 0.0135(5) Uani 1 1 d . . . . .
H10 H 0.6953 0.8961 0.8986 0.016 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
O1 C1 1.406(3) . ?
O1 C2 1.432(3) . ?
O2 C11 1.424(3) . ?
O2 H9 0.84(5) . ?
C1 H3 0.9800 . ?
C1 H12 0.9800 . ?
C1 H1 0.9800 . ?
C2 C3 1.512(3) . ?
C2 C11 1.529(3) . ?
C2 H11 1.0000 . ?
C3 C4 1.328(4) . ?
C3 H4 0.9500 . ?
C4 C5 1.460(3) . ?
C4 H5 0.9500 . ?
C5 C6 1.398(3) . ?
C5 C8 1.406(3) . ?
C6 C7 1.387(4) . ?
C6 H6 0.9500 . ?
C7 C10 1.387(4) . ?
C7 H2 0.9500 . ?
C8 C9 1.384(3) . ?
C8 C11 1.508(3) . ?
C9 C10 1.394(4) . ?
C9 H8 0.9500 . ?
C10 H7 0.9500 . ?
C11 H10 1.0000 . ?

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 C2 115.4(2) . . ?
C11 O2 H9 105(2) . . ?
O1 C1 H3 109.5 . . ?
O1 C1 H12 109.5 . . ?
H3 C1 H12 109.5 . . ?
O1 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
H12 C1 H1 109.5 . . ?
O1 C2 C3 106.41(19) . . ?
O1 C2 C11 112.16(19) . . ?
C3 C2 C11 109.30(19) . . ?
O1 C2 H11 109.6 . . ?
C3 C2 H11 109.6 . . ?
C11 C2 H11 109.6 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H4 119.9 . . ?
C2 C3 H4 119.9 . . ?
C3 C4 C5 122.1(2) . . ?
C3 C4 H5 118.9 . . ?
C5 C4 H5 118.9 . . ?
C6 C5 C8 119.3(2) . . ?
C6 C5 C4 121.6(2) . . ?
C8 C5 C4 119.0(2) . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C10 C7 C6 119.9(2) . . ?
C10 C7 H2 120.1 . . ?
C6 C7 H2 120.1 . . ?
C9 C8 C5 119.8(2) . . ?
C9 C8 C11 122.7(2) . . ?
C5 C8 C11 117.44(19) . . ?
C8 C9 C10 120.3(2) . . ?
C8 C9 H8 119.8 . . ?
C10 C9 H8 119.8 . . ?
C7 C10 C9 120.2(2) . . ?
C7 C10 H7 119.9 . . ?
C9 C10 H7 119.9 . . ?
O2 C11 C8 113.41(18) . . ?
O2 C11 C2 111.91(18) . . ?
C8 C11 C2 112.39(19) . . ?
O2 C11 H10 106.2 . . ?
C8 C11 H10 106.2 . . ?
C2 C11 H10 106.2 . . ?

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
C1 O1 C2 C3 138.8(2) . . . . ?
C1 O1 C2 C11 -101.7(2) . . . . ?
O1 C2 C3 C4 86.3(3) . . . . ?
C11 C2 C3 C4 -35.0(3) . . . . ?
C2 C3 C4 C5 3.1(4) . . . . ?
C3 C4 C5 C6 -164.3(2) . . . . ?
C3 C4 C5 C8 14.2(4) . . . . ?
C8 C5 C6 C7 -1.0(4) . . . . ?
C4 C5 C6 C7 177.5(2) . . . . ?
C5 C6 C7 C10 1.1(4) . . . . ?
C6 C5 C8 C9 0.1(3) . . . . ?
C4 C5 C8 C9 -178.4(2) . . . . ?
C6 C5 C8 C11 -177.4(2) . . . . ?
C4 C5 C8 C11 4.1(3) . . . . ?
C5 C8 C9 C10 0.7(3) . . . . ?
C11 C8 C9 C10 178.0(2) . . . . ?
C6 C7 C10 C9 -0.3(4) . . . . ?
C8 C9 C10 C7 -0.6(4) . . . . ?
C9 C8 C11 O2 17.8(3) . . . . ?
C5 C8 C11 O2 -164.84(19) . . . . ?
C9 C8 C11 C2 146.0(2) . . . . ?
C5 C8 C11 C2 -36.7(3) . . . . ?
O1 C2 C11 O2 61.4(3) . . . . ?
C3 C2 C11 O2 179.13(18) . . . . ?
O1 C2 C11 C8 -67.6(2) . . . . ?
C3 C2 C11 C8 50.2(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
O2 H9 O2 0.84(5) 1.88(4) 2.6980(16) 161(3) 2_467
O2 H9 O2 0.84(5) 1.88(4) 2.6980(16) 161(3) 2_467
O2 H9 O2 0.84(5) 1.88(4) 2.6980(16) 161(3) 2_467
O2 H9 O2 0.84(5) 1.88(4) 2.6980(16) 161(3) 2_467
O2 H9 O2 0.84(5) 1.88(4) 2.6980(16) 161(3) 2_467
O2 H9 O2 0.84(5) 1.88(4) 2.6980(16) 161(3) 2_467
O2 H9 O2 0.84(5) 1.88(4) 2.6980(16) 161(3) 2_467

_refine_diff_density_max         0.365
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.109

