# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_b
_database_code_depnum_ccdc_archive 'CCDC 1564032'
_audit_update_record             
;
2017-07-24 deposited with the CCDC.
2017-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 Cl2 O2'
_chemical_formula_weight         295.15

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0590(12)
_cell_length_b                   8.8930(18)
_cell_length_c                   13.346(3)
_cell_angle_alpha                91.59(3)
_cell_angle_beta                 93.75(3)
_cell_angle_gamma                108.42(3)
_cell_volume                     679.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      14

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.471
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.8716
_exptl_absorpt_correction_T_max  0.9544
_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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            2759
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         25.38
_reflns_number_total             2500
_reflns_number_gt                1874
_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)+(0.1000P)²+0.2500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2500
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1660
_refine_ls_wR_factor_gt          0.1484
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
Cl1 Cl 1.02670(18) 0.08063(11) 0.13626(8) 0.0653(3) Uani 1 1 d . . .
O1 O 1.1136(4) 0.4840(3) 0.38690(16) 0.0549(6) Uani 1 1 d . . .
H1B H 1.1331 0.5214 0.4449 0.082 Uiso 1 1 calc R . .
C1 C 0.6746(7) -0.0139(4) 0.3805(3) 0.0557(9) Uani 1 1 d . . .
H1A H 0.5590 0.0143 0.4112 0.067 Uiso 1 1 calc R . .
Cl2 Cl 0.42807(18) 0.81086(10) 0.05409(7) 0.0641(3) Uani 1 1 d . . .
O2 O 0.7543(4) 0.3760(3) 0.43140(16) 0.0519(6) Uani 1 1 d . . .
C2 C 0.7629(9) -0.1239(4) 0.4235(3) 0.0740(12) Uani 1 1 d . . .
H2A H 0.7048 -0.1700 0.4821 0.089 Uiso 1 1 calc R . .
C3 C 0.9361(9) -0.1659(4) 0.3808(3) 0.0754(13) Uani 1 1 d . . .
H3A H 0.9983 -0.2381 0.4112 0.090 Uiso 1 1 calc R . .
C4 C 1.0164(7) -0.1013(4) 0.2935(3) 0.0614(10) Uani 1 1 d . . .
H4A H 1.1320 -0.1305 0.2635 0.074 Uiso 1 1 calc R . .
C5 C 0.9262(6) 0.0073(3) 0.2499(2) 0.0458(8) Uani 1 1 d . . .
C6 C 0.7535(5) 0.0556(3) 0.2926(2) 0.0402(7) Uani 1 1 d . . .
C7 C 0.6563(5) 0.1774(3) 0.2480(2) 0.0405(7) Uani 1 1 d . . .
H7A H 0.5166 0.1748 0.2805 0.049 Uiso 1 1 calc R . .
H7B H 0.6116 0.1490 0.1772 0.049 Uiso 1 1 calc R . .
C8 C 0.8274(5) 0.3469(3) 0.2588(2) 0.0363(6) Uani 1 1 d . . .
H8A H 0.9674 0.3476 0.2258 0.044 Uiso 1 1 calc R . .
C9 C 0.9013(5) 0.4039(3) 0.3672(2) 0.0357(6) Uani 1 1 d . . .
C10 C 0.7248(5) 0.4635(3) 0.2070(2) 0.0366(6) Uani 1 1 d . . .
C11 C 0.8166(6) 0.5341(4) 0.1216(2) 0.0430(7) Uani 1 1 d . . .
H11A H 0.9412 0.5102 0.0959 0.052 Uiso 1 1 calc R . .
C12 C 0.7258(6) 0.6400(4) 0.0739(2) 0.0493(8) Uani 1 1 d . . .
H12A H 0.7877 0.6860 0.0159 0.059 Uiso 1 1 calc R . .
C13 C 0.5441(6) 0.6769(3) 0.1124(2) 0.0428(7) Uani 1 1 d . . .
C14 C 0.4496(6) 0.6089(4) 0.1972(2) 0.0462(7) Uani 1 1 d . . .
H14A H 0.3266 0.6348 0.2230 0.055 Uiso 1 1 calc R . .
C15 C 0.5390(6) 0.5012(4) 0.2440(2) 0.0448(7) Uani 1 1 d . . .
H15A H 0.4736 0.4535 0.3010 0.054 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C5 1.738(4) . ?
O1 C9 1.264(4) . ?
O1 H1B 0.8200 . ?
C1 C2 1.376(5) . ?
C1 C6 1.383(5) . ?
C1 H1A 0.9300 . ?
Cl2 C13 1.740(3) . ?
O2 C9 1.249(4) . ?
C2 C3 1.371(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.363(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.376(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.397(4) . ?
C6 C7 1.506(4) . ?
C7 C8 1.532(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.510(4) . ?
C8 C10 1.527(4) . ?
C8 H8A 0.9800 . ?
C10 C11 1.380(4) . ?
C10 C15 1.388(4) . ?
C11 C12 1.382(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.370(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.370(5) . ?
C14 C15 1.385(4) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?

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
C9 O1 H1B 109.5 . . ?
C2 C1 C6 121.6(4) . . ?
C2 C1 H1A 119.2 . . ?
C6 C1 H1A 119.2 . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C3 C4 C5 119.9(4) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C4 C5 C6 122.0(3) . . ?
C4 C5 Cl1 118.1(3) . . ?
C6 C5 Cl1 119.8(2) . . ?
C1 C6 C5 116.4(3) . . ?
C1 C6 C7 120.5(3) . . ?
C5 C6 C7 123.2(3) . . ?
C6 C7 C8 113.7(2) . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C10 109.0(2) . . ?
C9 C8 C7 112.7(2) . . ?
C10 C8 C7 111.4(2) . . ?
C9 C8 H8A 107.9 . . ?
C10 C8 H8A 107.9 . . ?
C7 C8 H8A 107.9 . . ?
O2 C9 O1 123.3(3) . . ?
O2 C9 C8 120.2(3) . . ?
O1 C9 C8 116.4(3) . . ?
C11 C10 C15 118.5(3) . . ?
C11 C10 C8 120.2(3) . . ?
C15 C10 C8 121.4(3) . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 H11A 119.6 . . ?
C12 C11 H11A 119.6 . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 H12A 120.2 . . ?
C11 C12 H12A 120.2 . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 Cl2 118.7(3) . . ?
C12 C13 Cl2 120.5(2) . . ?
C13 C14 C15 119.4(3) . . ?
C13 C14 H14A 120.3 . . ?
C15 C14 H14A 120.3 . . ?
C14 C15 C10 120.8(3) . . ?
C14 C15 H15A 119.6 . . ?
C10 C15 H15A 119.6 . . ?

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
C6 C1 C2 C3 1.0(6) . . . . ?
C1 C2 C3 C4 -1.8(6) . . . . ?
C2 C3 C4 C5 1.0(6) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C3 C4 C5 Cl1 -177.7(3) . . . . ?
C2 C1 C6 C5 0.4(5) . . . . ?
C2 C1 C6 C7 -179.1(3) . . . . ?
C4 C5 C6 C1 -1.2(4) . . . . ?
Cl1 C5 C6 C1 176.9(2) . . . . ?
C4 C5 C6 C7 178.3(3) . . . . ?
Cl1 C5 C6 C7 -3.6(4) . . . . ?
C1 C6 C7 C8 108.0(3) . . . . ?
C5 C6 C7 C8 -71.4(4) . . . . ?
C6 C7 C8 C9 -60.4(3) . . . . ?
C6 C7 C8 C10 176.7(2) . . . . ?
C10 C8 C9 O2 81.7(3) . . . . ?
C7 C8 C9 O2 -42.5(4) . . . . ?
C10 C8 C9 O1 -96.0(3) . . . . ?
C7 C8 C9 O1 139.8(3) . . . . ?
C9 C8 C10 C11 123.7(3) . . . . ?
C7 C8 C10 C11 -111.3(3) . . . . ?
C9 C8 C10 C15 -56.2(3) . . . . ?
C7 C8 C10 C15 68.8(3) . . . . ?
C15 C10 C11 C12 0.0(4) . . . . ?
C8 C10 C11 C12 -180.0(3) . . . . ?
C10 C11 C12 C13 0.8(5) . . . . ?
C11 C12 C13 C14 -0.7(5) . . . . ?
C11 C12 C13 Cl2 179.6(2) . . . . ?
C12 C13 C14 C15 -0.2(5) . . . . ?
Cl2 C13 C14 C15 179.5(2) . . . . ?
C13 C14 C15 C10 1.0(5) . . . . ?
C11 C10 C15 C14 -0.9(4) . . . . ?
C8 C10 C15 C14 179.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.072
####################################################################### 
# 
# 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_b_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1564033'
_audit_update_record             
;
2017-07-24 deposited with the CCDC.
2017-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H20 O2'
_chemical_formula_weight         268.34

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2600(17)
_cell_length_b                   10.221(2)
_cell_length_c                   10.602(2)
_cell_angle_alpha                102.50(3)
_cell_angle_beta                 107.52(3)
_cell_angle_gamma                109.03(3)
_cell_volume                     756.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9778
_exptl_absorpt_correction_T_max  0.9925
_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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            2984
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.38
_reflns_number_total             2776
_reflns_number_gt                1886
_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)+(0.1000P)²+0.2800P] 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       0.119(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2776
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.1912
_refine_ls_wR_factor_gt          0.1680
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 0.4944(3) 0.6652(2) 0.6498(2) 0.0454(6) Uani 1 1 d . . .
O1 O 0.8011(3) 0.4842(2) 0.9025(3) 0.0876(8) Uani 1 1 d . . .
O2 O 1.0578(3) 0.6919(2) 1.0010(2) 0.0713(7) Uani 1 1 d . . .
H2A H 1.1035 0.6390 1.0311 0.107 Uiso 1 1 calc R . .
C2 C 0.5619(4) 0.7387(3) 0.5661(3) 0.0492(6) Uani 1 1 d . . .
C3 C 0.4522(4) 0.7920(3) 0.4840(3) 0.0545(7) Uani 1 1 d . . .
H3A H 0.4983 0.8415 0.4296 0.065 Uiso 1 1 calc R . .
C4 C 0.2773(4) 0.7744(3) 0.4799(3) 0.0552(7) Uani 1 1 d . . .
C5 C 0.2144(4) 0.7041(3) 0.5638(3) 0.0556(7) Uani 1 1 d . . .
H5A H 0.0977 0.6924 0.5634 0.067 Uiso 1 1 calc R . .
C6 C 0.3195(4) 0.6496(3) 0.6496(3) 0.0496(6) Uani 1 1 d . . .
C7 C 0.7481(4) 0.7577(4) 0.5601(3) 0.0683(8) Uani 1 1 d . . .
H7A H 0.7692 0.8097 0.4972 0.102 Uiso 1 1 calc R . .
H7B H 0.7477 0.6624 0.5266 0.102 Uiso 1 1 calc R . .
H7C H 0.8459 0.8130 0.6528 0.102 Uiso 1 1 calc R . .
C8 C 0.1581(5) 0.8299(4) 0.3857(4) 0.0854(11) Uani 1 1 d . . .
H8A H 0.0426 0.8086 0.3975 0.128 Uiso 1 1 calc R . .
H8B H 0.1323 0.7817 0.2890 0.128 Uiso 1 1 calc R . .
H8C H 0.2241 0.9347 0.4112 0.128 Uiso 1 1 calc R . .
C9 C 0.2373(4) 0.5743(4) 0.7367(3) 0.0695(8) Uani 1 1 d . . .
H9A H 0.1172 0.5754 0.7213 0.104 Uiso 1 1 calc R . .
H9B H 0.3189 0.6254 0.8348 0.104 Uiso 1 1 calc R . .
H9C H 0.2232 0.4740 0.7099 0.104 Uiso 1 1 calc R . .
C10 C 0.6036(4) 0.5955(3) 0.7306(3) 0.0529(7) Uani 1 1 d . . .
H10A H 0.6427 0.5410 0.6680 0.063 Uiso 1 1 calc R . .
H10B H 0.5201 0.5245 0.7557 0.063 Uiso 1 1 calc R . .
C11 C 0.7785(3) 0.7016(3) 0.8664(3) 0.0480(6) Uani 1 1 d . . .
H11A H 0.8620 0.7741 0.8412 0.058 Uiso 1 1 calc R . .
C12 C 0.8796(4) 0.6144(3) 0.9243(3) 0.0498(6) Uani 1 1 d . . .
C13 C 0.7336(3) 0.7843(3) 0.9778(2) 0.0465(6) Uani 1 1 d . . .
C14 C 0.7575(4) 0.9292(3) 0.9958(3) 0.0580(7) Uani 1 1 d . . .
H14A H 0.8040 0.9764 0.9403 0.070 Uiso 1 1 calc R . .
C15 C 0.7127(5) 1.0031(3) 1.0952(4) 0.0742(9) Uani 1 1 d . . .
H15A H 0.7307 1.1004 1.1070 0.089 Uiso 1 1 calc R . .
C16 C 0.6421(5) 0.9358(4) 1.1771(3) 0.0778(10) Uani 1 1 d . . .
H16A H 0.6126 0.9869 1.2442 0.093 Uiso 1 1 calc R . .
C17 C 0.6150(5) 0.7918(4) 1.1595(3) 0.0755(9) Uani 1 1 d . . .
H17A H 0.5642 0.7440 1.2130 0.091 Uiso 1 1 calc R . .
C18 C 0.6640(4) 0.7185(3) 1.0617(3) 0.0615(8) Uani 1 1 d . . .
H18A H 0.6494 0.6223 1.0525 0.074 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.400(4) . ?
C1 C2 1.406(3) . ?
C1 C10 1.508(3) . ?
O1 C12 1.208(3) . ?
O2 C12 1.302(3) . ?
O2 H2A 0.8200 . ?
C2 C3 1.388(4) . ?
C2 C7 1.509(4) . ?
C3 C4 1.382(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.375(4) . ?
C4 C8 1.518(4) . ?
C5 C6 1.397(4) . ?
C5 H5A 0.9300 . ?
C6 C9 1.500(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.545(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.510(3) . ?
C11 C13 1.511(4) . ?
C11 H11A 0.9800 . ?
C13 C18 1.375(4) . ?
C13 C14 1.390(4) . ?
C14 C15 1.375(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.367(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.376(5) . ?
C16 H16A 0.9300 . ?
C17 C18 1.383(4) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?

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
C6 C1 C2 119.0(2) . . ?
C6 C1 C10 120.7(2) . . ?
C2 C1 C10 120.1(2) . . ?
C12 O2 H2A 109.5 . . ?
C3 C2 C1 119.2(2) . . ?
C3 C2 C7 119.1(2) . . ?
C1 C2 C7 121.7(2) . . ?
C4 C3 C2 122.5(3) . . ?
C4 C3 H3A 118.7 . . ?
C2 C3 H3A 118.7 . . ?
C5 C4 C3 117.6(2) . . ?
C5 C4 C8 121.0(3) . . ?
C3 C4 C8 121.4(3) . . ?
C4 C5 C6 122.3(2) . . ?
C4 C5 H5A 118.9 . . ?
C6 C5 H5A 118.9 . . ?
C5 C6 C1 119.3(2) . . ?
C5 C6 C9 117.9(2) . . ?
C1 C6 C9 122.8(2) . . ?
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 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 C10 C11 116.5(2) . . ?
C1 C10 H10A 108.2 . . ?
C11 C10 H10A 108.2 . . ?
C1 C10 H10B 108.2 . . ?
C11 C10 H10B 108.2 . . ?
H10A C10 H10B 107.3 . . ?
C12 C11 C13 110.2(2) . . ?
C12 C11 C10 108.9(2) . . ?
C13 C11 C10 113.2(2) . . ?
C12 C11 H11A 108.1 . . ?
C13 C11 H11A 108.1 . . ?
C10 C11 H11A 108.1 . . ?
O1 C12 O2 122.9(2) . . ?
O1 C12 C11 122.7(2) . . ?
O2 C12 C11 114.3(2) . . ?
C18 C13 C14 118.0(3) . . ?
C18 C13 C11 121.5(2) . . ?
C14 C13 C11 120.5(2) . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15A 119.5 . . ?
C14 C15 H15A 119.5 . . ?
C15 C16 C17 119.5(3) . . ?
C15 C16 H16A 120.3 . . ?
C17 C16 H16A 120.3 . . ?
C16 C17 C18 119.5(3) . . ?
C16 C17 H17A 120.2 . . ?
C18 C17 H17A 120.2 . . ?
C13 C18 C17 121.6(3) . . ?
C13 C18 H18A 119.2 . . ?
C17 C18 H18A 119.2 . . ?

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
C6 C1 C2 C3 -0.9(3) . . . . ?
C10 C1 C2 C3 175.0(2) . . . . ?
C6 C1 C2 C7 -179.2(2) . . . . ?
C10 C1 C2 C7 -3.4(4) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C7 C2 C3 C4 177.7(2) . . . . ?
C2 C3 C4 C5 1.6(4) . . . . ?
C2 C3 C4 C8 -178.2(2) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C8 C4 C5 C6 178.9(2) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C4 C5 C6 C9 -179.9(2) . . . . ?
C2 C1 C6 C5 1.5(3) . . . . ?
C10 C1 C6 C5 -174.3(2) . . . . ?
C2 C1 C6 C9 -179.3(2) . . . . ?
C10 C1 C6 C9 4.8(4) . . . . ?
C6 C1 C10 C11 -107.8(3) . . . . ?
C2 C1 C10 C11 76.5(3) . . . . ?
C1 C10 C11 C12 -174.4(2) . . . . ?
C1 C10 C11 C13 62.6(3) . . . . ?
C13 C11 C12 O1 98.5(3) . . . . ?
C10 C11 C12 O1 -26.3(4) . . . . ?
C13 C11 C12 O2 -80.8(3) . . . . ?
C10 C11 C12 O2 154.5(2) . . . . ?
C12 C11 C13 C18 -43.7(3) . . . . ?
C10 C11 C13 C18 78.5(3) . . . . ?
C12 C11 C13 C14 137.9(2) . . . . ?
C10 C11 C13 C14 -99.9(3) . . . . ?
C18 C13 C14 C15 0.2(4) . . . . ?
C11 C13 C14 C15 178.6(2) . . . . ?
C13 C14 C15 C16 -0.7(5) . . . . ?
C14 C15 C16 C17 -0.2(5) . . . . ?
C15 C16 C17 C18 1.6(5) . . . . ?
C14 C13 C18 C17 1.3(4) . . . . ?
C11 C13 C18 C17 -177.1(3) . . . . ?
C16 C17 C18 C13 -2.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.043
