# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_test_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1554775'
_audit_update_record             
;
2017-06-07 deposited with the CCDC.
2017-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H7 O'
_chemical_formula_weight         107.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   9.4379(9)
_cell_length_b                   12.1544(11)
_cell_length_c                   9.8277(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.8610(10)
_cell_angle_gamma                90.00
_cell_volume                     1119.28(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5437
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      25.39

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9810
_exptl_absorpt_correction_T_max  0.9834
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8285
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         25.39
_reflns_number_total             2061
_reflns_number_gt                1826
_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_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0642P)²+0.1645P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2061
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.78859(13) 0.48855(10) 0.61062(13) 0.0381(3) Uani 1 1 d . . .
C2 C 0.87686(15) 0.54898(12) 0.70486(14) 0.0476(4) Uani 1 1 d . . .
H2 H 0.9518 0.5910 0.6796 0.057 Uiso 1 1 calc R . .
C3 C 0.84692(17) 0.54311(13) 0.83927(15) 0.0543(4) Uani 1 1 d . . .
H3 H 0.9034 0.5822 0.9067 0.065 Uiso 1 1 calc R . .
C4 C 0.73477(17) 0.48031(12) 0.87562(14) 0.0532(4) Uani 1 1 d . . .
H4 H 0.7183 0.4781 0.9670 0.064 Uiso 1 1 calc R . .
C5 C 0.64677(15) 0.42096(11) 0.77988(13) 0.0450(3) Uani 1 1 d . . .
H5 H 0.5714 0.3795 0.8053 0.054 Uiso 1 1 calc R . .
C6 C 0.67476(13) 0.42521(10) 0.64358(12) 0.0364(3) Uani 1 1 d . . .
C7 C 0.61490(12) 0.37612(10) 0.51574(12) 0.0349(3) Uani 1 1 d . . .
C8 C 0.49614(13) 0.30102(11) 0.48032(13) 0.0385(3) Uani 1 1 d . . .
C9 C 0.46514(13) 0.27484(11) 0.32975(13) 0.0402(3) Uani 1 1 d . . .
H9A H 0.3987 0.3292 0.2875 0.048 Uiso 1 1 calc R . .
H9B H 0.4182 0.2038 0.3201 0.048 Uiso 1 1 calc R . .
C10 C 0.59671(13) 0.27200(10) 0.25033(12) 0.0357(3) Uani 1 1 d . . .
C11 C 0.67907(13) 0.38144(10) 0.27188(12) 0.0383(3) Uani 1 1 d . . .
H11A H 0.7724 0.3739 0.2409 0.046 Uiso 1 1 calc R . .
H11B H 0.6277 0.4391 0.2185 0.046 Uiso 1 1 calc R . .
C12 C 0.69531(12) 0.41140(10) 0.41890(12) 0.0347(3) Uani 1 1 d . . .
C13 C 0.69359(14) 0.17593(11) 0.30146(14) 0.0451(3) Uani 1 1 d . . .
H13A H 0.7283 0.1870 0.3963 0.068 Uiso 1 1 calc R . .
H13B H 0.7728 0.1721 0.2488 0.068 Uiso 1 1 calc R . .
H13C H 0.6405 0.1085 0.2913 0.068 Uiso 1 1 calc R . .
C14 C 0.54844(17) 0.25717(13) 0.09751(14) 0.0512(4) Uani 1 1 d . . .
H14A H 0.4976 0.1890 0.0830 0.077 Uiso 1 1 calc R . .
H14B H 0.6304 0.2562 0.0483 0.077 Uiso 1 1 calc R . .
H14C H 0.4870 0.3170 0.0652 0.077 Uiso 1 1 calc R . .
O1 O 0.80207(9) 0.48040(7) 0.47210(8) 0.0404(3) Uani 1 1 d . . .
O2 O 0.42580(11) 0.26328(9) 0.56586(11) 0.0596(3) 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 C2 1.3809(18) . ?
C1 O1 1.3859(15) . ?
C1 C6 1.3910(18) . ?
C2 C3 1.385(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3969(17) . ?
C5 H5 0.9300 . ?
C6 C7 1.4436(16) . ?
C7 C12 1.3558(17) . ?
C7 C8 1.4552(17) . ?
C8 O2 1.2211(15) . ?
C8 C9 1.5076(18) . ?
C9 C10 1.5440(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C14 1.5272(17) . ?
C10 C13 1.5305(17) . ?
C10 C11 1.5424(17) . ?
C11 C12 1.4802(17) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O1 1.3660(14) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C2 C1 O1 125.32(12) . . ?
C2 C1 C6 123.99(13) . . ?
O1 C1 C6 110.68(10) . . ?
C1 C2 C3 115.89(14) . . ?
C1 C2 H2 122.1 . . ?
C3 C2 H2 122.1 . . ?
C2 C3 C4 121.55(13) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.83(13) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 117.82(14) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C1 C6 C5 118.92(12) . . ?
C1 C6 C7 105.01(11) . . ?
C5 C6 C7 136.06(12) . . ?
C12 C7 C6 106.65(11) . . ?
C12 C7 C8 120.68(11) . . ?
C6 C7 C8 132.66(11) . . ?
O2 C8 C7 122.51(12) . . ?
O2 C8 C9 122.60(12) . . ?
C7 C8 C9 114.88(10) . . ?
C8 C9 C10 115.31(10) . . ?
C8 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
C10 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
C14 C10 C13 109.22(11) . . ?
C14 C10 C11 108.85(10) . . ?
C13 C10 C11 109.96(10) . . ?
C14 C10 C9 109.66(11) . . ?
C13 C10 C9 109.64(10) . . ?
C11 C10 C9 109.50(10) . . ?
C12 C11 C10 109.75(10) . . ?
C12 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C7 C12 O1 112.00(10) . . ?
C7 C12 C11 127.31(11) . . ?
O1 C12 C11 120.68(10) . . ?
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 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 O1 C1 105.65(9) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.39
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.093
####################################################################### 
# 
# 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_mo_20170607b_0ma
_database_code_depnum_ccdc_archive 'CCDC 1555510'
_audit_update_record             
;
2017-06-12 deposited with the CCDC.
2017-12-13 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         ?
_chemical_formula_sum            'C16 H16 O4'
_chemical_formula_weight         272.29

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.8746(6)
_cell_length_b                   15.3282(11)
_cell_length_c                   10.0135(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.182(2)
_cell_angle_gamma                90
_cell_volume                     1356.59(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9937
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      25.42

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23206
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.225
_diffrn_reflns_theta_max         25.417
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2484
_reflns_number_gt                2092
_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)+(0.0576P)²+0.6393P] 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         2484
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1189
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.025
_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 0.4806(2) 0.67549(12) 0.91192(18) 0.0481(4) Uani 1 1 d . . . . .
H1A H 0.4664 0.6483 0.9963 0.072 Uiso 1 1 calc R U . . .
H1B H 0.3847 0.6808 0.8599 0.072 Uiso 1 1 calc R U . . .
H1C H 0.5238 0.7324 0.9275 0.072 Uiso 1 1 calc R U . . .
C2 C 0.73543(19) 0.60520(12) 0.92257(17) 0.0477(4) Uani 1 1 d . . . . .
H2A H 0.8010 0.5687 0.8756 0.072 Uiso 1 1 calc R U . . .
H2B H 0.7148 0.5774 1.0049 0.072 Uiso 1 1 calc R U . . .
H2C H 0.7837 0.6604 0.9419 0.072 Uiso 1 1 calc R U . . .
C3 C 0.58714(17) 0.61964(10) 0.83548(14) 0.0347(4) Uani 1 1 d . . . . .
C4 C 0.61500(19) 0.66590(10) 0.70428(16) 0.0394(4) Uani 1 1 d . . . . .
H4A H 0.5195 0.6881 0.6630 0.047 Uiso 1 1 calc R U . . .
H4B H 0.6813 0.7154 0.7245 0.047 Uiso 1 1 calc R U . . .
C5 C 0.68373(16) 0.60811(10) 0.60726(14) 0.0323(3) Uani 1 1 d . . . . .
C6 C 0.68153(16) 0.51985(10) 0.60489(14) 0.0314(3) Uani 1 1 d . . . . .
C7 C 0.59212(19) 0.47595(10) 0.70348(16) 0.0392(4) Uani 1 1 d . . . . .
C8 C 0.51216(18) 0.53224(10) 0.79797(16) 0.0380(4) Uani 1 1 d . . . . .
H8A H 0.5031 0.4995 0.8797 0.046 Uiso 1 1 calc R U . . .
H8B H 0.4105 0.5435 0.7576 0.046 Uiso 1 1 calc R U . . .
C9 C 0.81984(17) 0.61869(11) 0.41153(15) 0.0376(4) Uani 1 1 d . . . . .
C10 C 0.82839(16) 0.52522(10) 0.40786(14) 0.0327(3) Uani 1 1 d . . . . .
C11 C 0.90547(17) 0.48483(11) 0.30706(15) 0.0388(4) Uani 1 1 d . . . . .
C12 C 0.91634(18) 0.39477(11) 0.30342(16) 0.0432(4) Uani 1 1 d . . . . .
H12 H 0.9667 0.3682 0.2367 0.052 Uiso 1 1 calc R U . . .
C13 C 0.85306(18) 0.34374(11) 0.39804(17) 0.0418(4) Uani 1 1 d . . . . .
C14 C 0.77477(18) 0.38316(10) 0.49747(15) 0.0376(4) Uani 1 1 d . . . . .
H14 H 0.7315 0.3485 0.5600 0.045 Uiso 1 1 calc R U . . .
C15 C 0.76090(15) 0.47354(10) 0.50381(14) 0.0314(3) Uani 1 1 d . . . . .
C16 C 0.8689(2) 0.24606(12) 0.3950(2) 0.0615(6) Uani 1 1 d . . . . .
H16A H 0.7767 0.2207 0.3548 0.092 Uiso 1 1 calc R U . . .
H16B H 0.8891 0.2245 0.4848 0.092 Uiso 1 1 calc R U . . .
H16C H 0.9509 0.2306 0.3434 0.092 Uiso 1 1 calc R U . . .
O1 O 0.5743(2) 0.39748(8) 0.70557(16) 0.0794(6) Uani 1 1 d . . . . .
O2 O 0.75194(12) 0.65664(7) 0.51469(11) 0.0393(3) Uani 1 1 d . . . . .
O3 O 0.86982(15) 0.66941(8) 0.33217(13) 0.0540(4) Uani 1 1 d . . . . .
O4 O 0.97092(15) 0.53141(9) 0.21332(12) 0.0545(4) Uani 1 1 d . . . . .
H4 H 0.9577 0.5836 0.2258 0.082 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 C3 1.531(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.528(2) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C8 1.528(2) . ?
C3 C4 1.532(2) . ?
C4 C5 1.486(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.353(2) . ?
C5 O2 1.3713(17) . ?
C6 C15 1.467(2) . ?
C6 C7 1.483(2) . ?
C7 O1 1.213(2) . ?
C7 C8 1.505(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O3 1.2233(19) . ?
C9 O2 1.3715(18) . ?
C9 C10 1.435(2) . ?
C10 C11 1.412(2) . ?
C10 C15 1.419(2) . ?
C11 O4 1.3515(19) . ?
C11 C12 1.384(2) . ?
C12 C13 1.386(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.401(2) . ?
C13 C16 1.504(2) . ?
C14 C15 1.393(2) . ?
C14 H14 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O4 H4 0.8200 . ?

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 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C8 C3 C2 110.30(13) . . ?
C8 C3 C1 109.77(13) . . ?
C2 C3 C1 109.56(13) . . ?
C8 C3 C4 107.19(12) . . ?
C2 C3 C4 111.04(13) . . ?
C1 C3 C4 108.95(13) . . ?
C5 C4 C3 113.09(12) . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C6 C5 O2 122.48(13) . . ?
C6 C5 C4 126.97(13) . . ?
O2 C5 C4 110.55(12) . . ?
C5 C6 C15 119.25(13) . . ?
C5 C6 C7 116.73(13) . . ?
C15 C6 C7 123.97(14) . . ?
O1 C7 C6 122.65(14) . . ?
O1 C7 C8 119.21(14) . . ?
C6 C7 C8 118.00(13) . . ?
C7 C8 C3 115.96(12) . . ?
C7 C8 H8A 108.3 . . ?
C3 C8 H8A 108.3 . . ?
C7 C8 H8B 108.3 . . ?
C3 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
O3 C9 O2 115.43(15) . . ?
O3 C9 C10 126.49(15) . . ?
O2 C9 C10 118.07(13) . . ?
C11 C10 C15 120.03(15) . . ?
C11 C10 C9 119.08(14) . . ?
C15 C10 C9 120.89(13) . . ?
O4 C11 C12 118.24(14) . . ?
O4 C11 C10 122.07(15) . . ?
C12 C11 C10 119.69(14) . . ?
C11 C12 C13 120.74(15) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C14 119.99(15) . . ?
C12 C13 C16 120.23(15) . . ?
C14 C13 C16 119.78(16) . . ?
C15 C14 C13 120.85(15) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C10 118.69(13) . . ?
C14 C15 C6 124.23(13) . . ?
C10 C15 C6 117.08(14) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C5 O2 C9 121.99(12) . . ?
C11 O4 H4 109.5 . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.039

