# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1417743'
_audit_update_record             
;
2015-08-10 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 Cl4 O3'
_chemical_formula_weight         329.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 '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'
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'

_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                   6.5579(7)
_cell_length_b                   7.6349(6)
_cell_length_c                   15.6331(14)
_cell_angle_alpha                84.549(7)
_cell_angle_beta                 86.322(8)
_cell_angle_gamma                78.859(8)
_cell_volume                     763.67(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      8.239
_cell_measurement_theta_max      71.949

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.770
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.710
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4489
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.618
_diffrn_reflns_theta_max         26.015
_diffrn_reflns_theta_full        25.214
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2890
_reflns_number_gt                2455
_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 (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)+(0.9500P)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     SHELXL
_refine_ls_extinction_coef       0.13(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2890
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3172
_refine_ls_R_factor_gt           0.3061
_refine_ls_wR_factor_ref         0.7473
_refine_ls_wR_factor_gt          0.7294
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
Cl1 Cl 0.2314(7) 0.1368(7) 0.5737(2) 0.0694(19) Uani 1 1 d . . . . .
Cl2 Cl -0.2287(6) 0.3483(6) 0.5715(2) 0.0628(18) Uani 1 1 d . . . . .
Cl3 Cl 0.2946(7) -0.0632(5) 0.2321(3) 0.070(2) Uani 1 1 d . . . . .
Cl4 Cl 0.3958(6) 0.4790(4) 0.2292(2) 0.0514(17) Uani 1 1 d . . . . .
O1 O 0.4185(16) 0.2516(14) 0.0724(7) 0.051(3) Uiso 1 1 d . . . . .
O2 O 0.667(2) -0.0773(17) 0.0700(9) 0.067(3) Uiso 1 1 d . . . . .
O3 O 0.7738(16) -0.0646(11) 0.1966(6) 0.047(3) Uani 1 1 d . . . . .
C1 C 0.116(2) 0.2071(19) 0.4795(8) 0.049(3) Uani 1 1 d . . . . .
C2 C -0.0849(19) 0.2979(16) 0.4785(8) 0.041(3) Uani 1 1 d . . . . .
C3 C -0.1769(17) 0.359(2) 0.4004(9) 0.046(3) Uani 1 1 d . . . . .
H6 H -0.3114 0.4253 0.3995 0.055 Uiso 1 1 calc R U . . .
C4 C -0.066(2) 0.318(2) 0.3246(9) 0.053(4) Uani 1 1 d . . . . .
H15 H -0.1280 0.3554 0.2726 0.064 Uiso 1 1 calc R U . . .
C5 C 0.135(2) 0.224(2) 0.3243(10) 0.052(4) Uani 1 1 d . . . . .
C6 C 0.227(2) 0.168(2) 0.4027(10) 0.053(4) Uani 1 1 d . . . . .
H8 H 0.3628 0.1039 0.4036 0.064 Uiso 1 1 calc R U . . .
C7 C 0.242(2) 0.172(2) 0.2403(11) 0.056(4) Uani 1 1 d . . . . .
H11 H 0.1486 0.2267 0.1946 0.067 Uiso 1 1 calc R U . . .
C8 C 0.4561(19) 0.2415(18) 0.2206(8) 0.043(3) Uani 1 1 d . . . . .
H9 H 0.5503 0.1876 0.2661 0.051 Uiso 1 1 calc R U . . .
C9 C 0.571(2) 0.2037(17) 0.1338(7) 0.044(3) Uani 1 1 d . . . . .
C10 C 0.6652(18) 0.0057(17) 0.1276(7) 0.039(3) Uani 1 1 d . . . . .
C11 C 0.873(3) -0.248(2) 0.1997(13) 0.064(4) Uani 1 1 d . . . . .
H17A H 0.9719 -0.2663 0.1518 0.096 Uiso 1 1 calc R U . . .
H17B H 0.7703 -0.3215 0.1967 0.096 Uiso 1 1 calc R U . . .
H17C H 0.9433 -0.2809 0.2524 0.096 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
Cl1 C1 1.693(13) . ?
Cl2 C2 1.714(12) . ?
Cl3 C7 1.778(15) . ?
Cl4 C8 1.796(13) . ?
O1 C9 1.403(16) . ?
O2 C10 1.149(18) . ?
O3 C10 1.341(15) . ?
O3 C11 1.425(16) . ?
C1 C6 1.39(2) . ?
C1 C2 1.364(19) . ?
C2 C3 1.40(2) . ?
C3 C4 1.38(2) . ?
C4 C5 1.37(2) . ?
C5 C6 1.39(2) . ?
C5 C7 1.501(18) . ?
C7 C8 1.60(2) . ?
C8 C9 1.533(17) . ?
C9 C10 1.529(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
C10 O3 C11 118.3(12) . . ?
C6 C1 C2 120.1(13) . . ?
C6 C1 Cl1 119.1(11) . . ?
C2 C1 Cl1 120.8(11) . . ?
C3 C2 C1 120.2(12) . . ?
C3 C2 Cl2 117.9(9) . . ?
C1 C2 Cl2 121.9(11) . . ?
C4 C3 C2 119.1(11) . . ?
C5 C4 C3 121.5(13) . . ?
C4 C5 C6 118.9(13) . . ?
C4 C5 C7 119.0(15) . . ?
C6 C5 C7 121.9(13) . . ?
C1 C6 C5 120.1(13) . . ?
C5 C7 C8 113.6(12) . . ?
C5 C7 Cl3 113.1(12) . . ?
C8 C7 Cl3 107.5(9) . . ?
C9 C8 C7 117.3(11) . . ?
C9 C8 Cl4 109.4(9) . . ?
C7 C8 Cl4 106.0(8) . . ?
O1 C9 C10 107.4(10) . . ?
O1 C9 C8 105.5(10) . . ?
C10 C9 C8 113.0(10) . . ?
O2 C10 O3 120.1(12) . . ?
O2 C10 C9 127.6(12) . . ?
O3 C10 C9 111.9(9) . . ?

_refine_diff_density_max         6.501
_refine_diff_density_min         -1.439
_refine_diff_density_rms         0.461

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1417744'
_audit_update_record             
;
2015-08-10 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 Cl2 O3'
_chemical_formula_weight         311.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.3639 0.7018 '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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.1786(3)
_cell_length_b                   20.0394(12)
_cell_length_c                   20.1954(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2905.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      4.849
_cell_measurement_theta_max      72.161

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    4.061
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.110
_exptl_absorpt_correction_T_max  0.305
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5886
_diffrn_reflns_av_unetI/netI     0.1010
_diffrn_reflns_av_R_equivalents  0.1576
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.379
_diffrn_reflns_theta_max         72.064
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.802
_diffrn_measured_fraction_theta_full 0.818
_diffrn_reflns_Laue_measured_fraction_max 0.802
_diffrn_reflns_Laue_measured_fraction_full 0.818
_diffrn_reflns_point_group_measured_fraction_max 0.802
_diffrn_reflns_point_group_measured_fraction_full 0.818
_reflns_number_total             2295
_reflns_number_gt                1881
_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 (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)+(0.2900P)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     SHELXL
_refine_ls_extinction_coef       0.0036(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2295
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.1240
_refine_ls_wR_factor_ref         0.3637
_refine_ls_wR_factor_gt          0.3392
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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
Cl1 Cl 0.37081(17) 0.82652(8) 0.23229(8) 0.0795(7) Uani 1 1 d . . . . .
Cl2 Cl 0.2339(2) 0.75195(6) 0.03756(6) 0.0742(7) Uani 1 1 d . . . . .
O1 O 0.2888(6) 0.91123(18) 0.0968(4) 0.107(2) Uani 1 1 d . . . . .
O2 O -0.1464(4) 0.84280(17) 0.0882(2) 0.0660(10) Uani 1 1 d . . . . .
O3 O -0.0253(5) 0.92161(15) 0.0227(2) 0.0653(10) Uani 1 1 d . . . . .
C1 C 0.3380(6) 0.6687(2) 0.1901(2) 0.0561(12) Uani 1 1 d . . . . .
H2 H 0.2233 0.6831 0.2061 0.067 Uiso 1 1 calc R U . . .
C2 C 0.3849(6) 0.6032(2) 0.1949(2) 0.0568(12) Uani 1 1 d . . . . .
H3 H 0.3007 0.5733 0.2134 0.068 Uiso 1 1 calc R U . . .
C3 C 0.5605(6) 0.5798(2) 0.17210(19) 0.0496(10) Uani 1 1 d . . . . .
C4 C 0.6149(7) 0.5123(2) 0.1792(3) 0.0610(12) Uani 1 1 d . . . . .
H5 H 0.5315 0.4815 0.1967 0.073 Uiso 1 1 calc R U . . .
C5 C 0.7881(8) 0.4922(3) 0.1606(3) 0.0713(15) Uani 1 1 d . . . . .
H6 H 0.8233 0.4480 0.1667 0.086 Uiso 1 1 calc R U . . .
C6 C 0.9160(8) 0.5381(3) 0.1321(3) 0.0742(15) Uani 1 1 d . . . . .
H7 H 1.0340 0.5238 0.1194 0.089 Uiso 1 1 calc R U . . .
C7 C 0.8652(7) 0.6028(3) 0.1233(3) 0.0626(12) Uani 1 1 d . . . . .
H8 H 0.9484 0.6324 0.1037 0.075 Uiso 1 1 calc R U . . .
C8 C 0.6855(6) 0.6261(2) 0.1438(2) 0.0496(10) Uani 1 1 d . . . . .
C9 C 0.6321(5) 0.6937(2) 0.1382(2) 0.0482(10) Uani 1 1 d . . . . .
H10 H 0.7138 0.7239 0.1186 0.058 Uiso 1 1 calc R U . . .
C10 C 0.4640(6) 0.71608(19) 0.16069(19) 0.0471(10) Uani 1 1 d . . . . .
C11 C 0.4062(6) 0.7872(2) 0.1525(2) 0.0556(11) Uani 1 1 d . . . . .
H11 H 0.5048 0.8111 0.1289 0.067 Uiso 1 1 calc R U . . .
C12 C 0.2256(6) 0.79588(19) 0.1152(2) 0.0509(10) Uani 1 1 d . . . . .
H12 H 0.1230 0.7782 0.1420 0.061 Uiso 1 1 calc R U . . .
C13 C 0.1791(7) 0.8662(2) 0.0939(3) 0.0648(14) Uani 1 1 d . . . . .
C14 C -0.0193(5) 0.87521(19) 0.0677(2) 0.0517(11) Uani 1 1 d . . . . .
C15 C -0.2067(9) 0.9345(3) -0.0085(3) 0.0751(15) Uani 1 1 d . . . . .
H16A H -0.1939 0.9696 -0.0405 0.113 Uiso 1 1 calc R U . . .
H16B H -0.2950 0.9476 0.0247 0.113 Uiso 1 1 calc R U . . .
H16C H -0.2496 0.8947 -0.0301 0.113 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
Cl1 C11 1.811(5) . ?
Cl2 C12 1.800(5) . ?
O1 C13 1.198(6) . ?
O2 C14 1.194(5) . ?
O3 C14 1.301(6) . ?
O3 C15 1.469(7) . ?
C1 C2 1.358(7) . ?
C1 C10 1.439(6) . ?
C2 C3 1.422(6) . ?
C3 C8 1.413(6) . ?
C3 C4 1.415(6) . ?
C4 C5 1.360(8) . ?
C5 C6 1.421(9) . ?
C6 C7 1.359(8) . ?
C7 C8 1.433(6) . ?
C8 C9 1.412(7) . ?
C9 C10 1.365(6) . ?
C10 C11 1.493(6) . ?
C11 C12 1.510(6) . ?
C12 C13 1.512(7) . ?
C13 C14 1.529(6) . ?

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
C14 O3 C15 117.1(4) . . ?
C2 C1 C10 120.7(4) . . ?
C1 C2 C3 121.1(4) . . ?
C8 C3 C4 119.6(4) . . ?
C8 C3 C2 118.5(4) . . ?
C4 C3 C2 121.9(4) . . ?
C5 C4 C3 120.5(5) . . ?
C4 C5 C6 120.7(5) . . ?
C7 C6 C5 119.8(5) . . ?
C6 C7 C8 121.0(5) . . ?
C9 C8 C3 119.4(4) . . ?
C9 C8 C7 122.3(4) . . ?
C3 C8 C7 118.3(4) . . ?
C10 C9 C8 121.9(4) . . ?
C9 C10 C1 118.5(4) . . ?
C9 C10 C11 121.5(4) . . ?
C1 C10 C11 120.0(4) . . ?
C10 C11 C12 113.8(4) . . ?
C10 C11 Cl1 110.9(3) . . ?
C12 C11 Cl1 105.9(3) . . ?
C11 C12 C13 116.1(4) . . ?
C11 C12 Cl2 110.5(3) . . ?
C13 C12 Cl2 102.4(4) . . ?
O1 C13 C12 122.9(5) . . ?
O1 C13 C14 122.7(4) . . ?
C12 C13 C14 114.4(4) . . ?
O2 C14 O3 127.2(4) . . ?
O2 C14 C13 121.9(4) . . ?
O3 C14 C13 110.9(4) . . ?

_refine_diff_density_max         0.928
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.137

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_160602c
_database_code_depnum_ccdc_archive 'CCDC 1495828'
_audit_update_record             
;
2016-07-25 deposited with the CCDC.
2016-09-01 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            'C29 H48 Cl2 O2'
_chemical_formula_weight         499.57


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'
Cl Cl 0.3639 0.7018 '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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.2490(6)
_cell_length_b                   7.6979(4)
_cell_length_c                   19.7126(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.778(6)
_cell_angle_gamma                90
_cell_volume                     1547.35(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.033
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5564
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         6.176
_diffrn_reflns_theta_max         72.305
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.577
_diffrn_reflns_point_group_measured_fraction_full 0.594
_reflns_number_total             3527
_reflns_number_gt                3061
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.114
_reflns_Friedel_fraction_max     0.129
_reflns_Friedel_fraction_full    0.137

_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)+(0.1187P)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_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.03(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3527
_refine_ls_number_parameters     304
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1649
_refine_ls_wR_factor_gt          0.1551
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
Cl1 Cl -0.65699(9) -0.20084(17) -0.29030(5) 0.0663(3) Uani 1 1 d . . . . .
Cl2 Cl -0.94094(15) 0.05984(17) -0.17959(7) 0.0798(4) Uani 1 1 d . . . . .
C5 C -0.7853(4) -0.1933(5) -0.22998(18) 0.0518(8) Uani 1 1 d . . . . .
C15 C -1.1099(4) -0.4554(5) -0.4152(2) 0.0569(9) Uani 1 1 d . . . . .
H15A H -1.0455 -0.4615 -0.4479 0.068 Uiso 1 1 calc R U . . .
H15B H -1.1715 -0.5499 -0.4248 0.068 Uiso 1 1 calc R U . . .
C4 C -0.7088(4) -0.2088(6) -0.1595(2) 0.0614(9) Uani 1 1 d . . . . .
H4A H -0.7690 -0.1975 -0.1248 0.074 Uiso 1 1 calc R U . . .
H4B H -0.6458 -0.1146 -0.1533 0.074 Uiso 1 1 calc R U . . .
C3 C -0.6365(5) -0.3824(7) -0.1503(2) 0.0670(11) Uani 1 1 d . . . . .
H3 H -0.5633 -0.3850 -0.1787 0.080 Uiso 1 1 calc R U . . .
C12 C -1.0188(3) -0.1497(5) -0.33083(19) 0.0471(7) Uani 1 1 d . . . . .
H12 H -1.0882 -0.1430 -0.3002 0.057 Uiso 1 1 calc R U . . .
C6 C -0.9863(5) -0.3546(7) -0.1950(2) 0.0633(10) Uani 1 1 d . . . . .
H6A H -0.9460 -0.3274 -0.1502 0.095 Uiso 1 1 calc R U . . .
H6B H -1.0239 -0.4687 -0.1949 0.095 Uiso 1 1 calc R U . . .
H6C H -1.0538 -0.2712 -0.2081 0.095 Uiso 1 1 calc R U . . .
C9 C -0.8817(4) -0.3486(5) -0.24635(19) 0.0485(8) Uani 1 1 d . . . . .
C8 C -0.7254(5) -0.5357(6) -0.1671(2) 0.0674(11) Uani 1 1 d . . . . .
H8A H -0.7875 -0.5450 -0.1332 0.081 Uiso 1 1 calc R U . . .
H8B H -0.6736 -0.6413 -0.1653 0.081 Uiso 1 1 calc R U . . .
C17 C -1.1830(3) -0.2830(5) -0.42366(19) 0.0475(7) Uani 1 1 d . . . . .
C18 C -1.0805(3) -0.1382(5) -0.40382(19) 0.0470(7) Uani 1 1 d . . . . .
H18 H -1.0093 -0.1548 -0.4329 0.056 Uiso 1 1 calc R U . . .
C7 C -0.8007(5) -0.5172(6) -0.2384(2) 0.0601(10) Uani 1 1 d . . . . .
H7A H -0.7386 -0.5191 -0.2724 0.072 Uiso 1 1 calc R U . . .
H7B H -0.8590 -0.6159 -0.2468 0.072 Uiso 1 1 calc R U . . .
C13 C -0.9484(4) -0.3269(5) -0.32045(19) 0.0483(8) Uani 1 1 d . . . . .
H13 H -0.8779 -0.3276 -0.3506 0.058 Uiso 1 1 calc R U . . .
C11 C -0.9231(4) 0.0006(5) -0.3148(2) 0.0563(9) Uani 1 1 d . . . . .
H11A H -0.8632 0.0053 -0.3499 0.068 Uiso 1 1 calc R U . . .
H11B H -0.9722 0.1085 -0.3168 0.068 Uiso 1 1 calc R U . . .
C10 C -0.8433(4) -0.0122(6) -0.2454(2) 0.0570(9) Uani 1 1 d . . . . .
H10 H -0.7696 0.0687 -0.2459 0.068 Uiso 1 1 calc R U . . .
C1 C -0.4331(11) -0.3603(13) 0.0158(4) 0.142(4) Uani 1 1 d . . . . .
H1A H -0.3951 -0.4740 0.0212 0.214 Uiso 1 1 calc R U . . .
H1B H -0.5089 -0.3534 0.0406 0.214 Uiso 1 1 calc R U . . .
H1C H -0.3700 -0.2749 0.0330 0.214 Uiso 1 1 calc R U . . .
C2 C -0.4727(7) -0.3268(9) -0.0582(3) 0.0920(19) Uani 1 1 d . . . . .
C21 C -1.2296(3) -0.2252(5) -0.49783(18) 0.0486(8) Uani 1 1 d . . . . .
H21 H -1.1582 -0.2510 -0.5258 0.058 Uiso 1 1 calc R U . . .
C23 C -1.3559(4) -0.3072(6) -0.53399(19) 0.0531(8) Uani 1 1 d . . . . .
H23 H -1.4295 -0.2738 -0.5086 0.064 Uiso 1 1 calc R U . . .
C24 C -1.3817(4) -0.2332(6) -0.6067(2) 0.0591(10) Uani 1 1 d . . . . .
H24A H -1.3762 -0.1076 -0.6042 0.071 Uiso 1 1 calc R U . . .
H24B H -1.3128 -0.2732 -0.6332 0.071 Uiso 1 1 calc R U . . .
C20 C -1.2390(4) -0.0241(6) -0.4924(2) 0.0586(9) Uani 1 1 d . . . . .
H20A H -1.2091 0.0303 -0.5325 0.070 Uiso 1 1 calc R U . . .
H20B H -1.3290 0.0109 -0.4889 0.070 Uiso 1 1 calc R U . . .
C22 C -1.3499(5) -0.5054(7) -0.5359(2) 0.0634(10) Uani 1 1 d . . . . .
H22A H -1.2692 -0.5412 -0.5525 0.095 Uiso 1 1 calc R U . . .
H22B H -1.4225 -0.5490 -0.5655 0.095 Uiso 1 1 calc R U . . .
H22C H -1.3541 -0.5506 -0.4907 0.095 Uiso 1 1 calc R U . . .
C16 C -1.2982(4) -0.2786(7) -0.3795(2) 0.0599(9) Uani 1 1 d . . . . .
H16A H -1.3556 -0.3750 -0.3912 0.090 Uiso 1 1 calc R U . . .
H16B H -1.3458 -0.1719 -0.3874 0.090 Uiso 1 1 calc R U . . .
H16C H -1.2653 -0.2862 -0.3322 0.090 Uiso 1 1 calc R U . . .
O2 O -0.4144(5) -0.2379(9) -0.0935(3) 0.1161(18) Uani 1 1 d . . . . .
O1 O -0.5875(4) -0.4039(5) -0.07902(17) 0.0820(10) Uani 1 1 d . . . . .
C14 C -1.0406(5) -0.4780(5) -0.3433(3) 0.0626(11) Uani 1 1 d . . . . .
H14A H -0.9903 -0.5849 -0.3417 0.075 Uiso 1 1 calc R U . . .
H14B H -1.1063 -0.4892 -0.3114 0.075 Uiso 1 1 calc R U . . .
C19 C -1.1513(4) 0.0304(5) -0.4281(2) 0.0564(9) Uani 1 1 d . . . . .
H19A H -1.2036 0.0751 -0.3936 0.068 Uiso 1 1 calc R U . . .
H19B H -1.0890 0.1187 -0.4387 0.068 Uiso 1 1 calc R U . . .
C26 C -1.5375(4) -0.2002(8) -0.7143(2) 0.0673(10) Uani 1 1 d . . . . .
H26A H -1.4657 -0.2318 -0.7404 0.081 Uiso 1 1 calc R U . . .
H26B H -1.5357 -0.0750 -0.7089 0.081 Uiso 1 1 calc R U . . .
C25 C -1.5136(4) -0.2828(7) -0.6441(2) 0.0615(10) Uani 1 1 d . . . . .
H25A H -1.5179 -0.4081 -0.6489 0.074 Uiso 1 1 calc R U . . .
H25B H -1.5829 -0.2473 -0.6170 0.074 Uiso 1 1 calc R U . . .
C27 C -1.6671(5) -0.2509(9) -0.7558(2) 0.0763(15) Uani 1 1 d . . . . .
H27 H -1.7378 -0.2329 -0.7266 0.092 Uiso 1 1 calc R U . . .
C29 C -1.6696(7) -0.4411(12) -0.7766(3) 0.0995(19) Uani 1 1 d . . . . .
H29A H -1.6053 -0.4609 -0.8080 0.149 Uiso 1 1 calc R U . . .
H29B H -1.7550 -0.4702 -0.7980 0.149 Uiso 1 1 calc R U . . .
H29C H -1.6499 -0.5122 -0.7369 0.149 Uiso 1 1 calc R U . . .
C28 C -1.6934(7) -0.1329(13) -0.8170(3) 0.106(2) Uani 1 1 d . . . . .
H28A H -1.6752 -0.0149 -0.8036 0.159 Uiso 1 1 calc R U . . .
H28B H -1.7837 -0.1432 -0.8350 0.159 Uiso 1 1 calc R U . . .
H28C H -1.6381 -0.1660 -0.8514 0.159 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
Cl1 C5 1.860(4) . ?
Cl2 C10 1.804(5) . ?
C5 C4 1.530(5) . ?
C5 C10 1.534(6) . ?
C5 C9 1.564(5) . ?
C15 C17 1.525(5) . ?
C15 C14 1.529(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C4 C3 1.530(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 O1 1.453(5) . ?
C3 C8 1.507(7) . ?
C3 H3 0.9800 . ?
C12 C18 1.515(5) . ?
C12 C11 1.529(5) . ?
C12 C13 1.547(5) . ?
C12 H12 0.9800 . ?
C6 C9 1.547(6) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C9 C7 1.540(5) . ?
C9 C13 1.558(5) . ?
C8 C7 1.541(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C17 C16 1.537(5) . ?
C17 C18 1.554(5) . ?
C17 C21 1.557(5) . ?
C18 C19 1.540(5) . ?
C18 H18 0.9800 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C13 C14 1.537(5) . ?
C13 H13 0.9800 . ?
C11 C10 1.525(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C10 H10 0.9800 . ?
C1 C2 1.496(9) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O2 1.181(9) . ?
C2 O1 1.344(8) . ?
C21 C23 1.548(5) . ?
C21 C20 1.555(6) . ?
C21 H21 0.9800 . ?
C23 C22 1.528(7) . ?
C23 C24 1.540(5) . ?
C23 H23 0.9800 . ?
C24 C25 1.522(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C20 C19 1.536(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C26 C25 1.520(6) . ?
C26 C27 1.538(6) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C27 C28 1.513(9) . ?
C27 C29 1.520(11) . ?
C27 H27 0.9800 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 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
C4 C5 C10 113.8(3) . . ?
C4 C5 C9 112.5(3) . . ?
C10 C5 C9 115.4(3) . . ?
C4 C5 Cl1 104.3(3) . . ?
C10 C5 Cl1 100.7(3) . . ?
C9 C5 Cl1 108.5(3) . . ?
C17 C15 C14 112.2(3) . . ?
C17 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C17 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C5 C4 C3 111.9(4) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
O1 C3 C8 105.4(4) . . ?
O1 C3 C4 109.3(4) . . ?
C8 C3 C4 112.5(4) . . ?
O1 C3 H3 109.9 . . ?
C8 C3 H3 109.9 . . ?
C4 C3 H3 109.9 . . ?
C18 C12 C11 110.4(3) . . ?
C18 C12 C13 108.8(3) . . ?
C11 C12 C13 111.0(3) . . ?
C18 C12 H12 108.9 . . ?
C11 C12 H12 108.9 . . ?
C13 C12 H12 108.9 . . ?
C9 C6 H6A 109.5 . . ?
C9 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C9 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C7 C9 C6 108.1(3) . . ?
C7 C9 C13 111.5(3) . . ?
C6 C9 C13 110.4(3) . . ?
C7 C9 C5 107.5(3) . . ?
C6 C9 C5 110.7(3) . . ?
C13 C9 C5 108.7(3) . . ?
C3 C8 C7 111.4(4) . . ?
C3 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C3 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C15 C17 C16 110.7(4) . . ?
C15 C17 C18 106.5(3) . . ?
C16 C17 C18 112.4(3) . . ?
C15 C17 C21 116.9(3) . . ?
C16 C17 C21 110.2(3) . . ?
C18 C17 C21 99.6(3) . . ?
C12 C18 C19 118.9(3) . . ?
C12 C18 C17 113.8(3) . . ?
C19 C18 C17 103.9(3) . . ?
C12 C18 H18 106.5 . . ?
C19 C18 H18 106.5 . . ?
C17 C18 H18 106.5 . . ?
C9 C7 C8 112.7(4) . . ?
C9 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C9 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C14 C13 C12 111.3(3) . . ?
C14 C13 C9 113.1(3) . . ?
C12 C13 C9 111.9(3) . . ?
C14 C13 H13 106.7 . . ?
C12 C13 H13 106.7 . . ?
C9 C13 H13 106.7 . . ?
C10 C11 C12 114.3(3) . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C11 C10 C5 113.5(3) . . ?
C11 C10 Cl2 109.8(3) . . ?
C5 C10 Cl2 111.6(3) . . ?
C11 C10 H10 107.2 . . ?
C5 C10 H10 107.2 . . ?
Cl2 C10 H10 107.2 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 123.7(5) . . ?
O2 C2 C1 124.8(7) . . ?
O1 C2 C1 111.4(7) . . ?
C23 C21 C20 112.5(3) . . ?
C23 C21 C17 118.7(3) . . ?
C20 C21 C17 103.6(3) . . ?
C23 C21 H21 107.2 . . ?
C20 C21 H21 107.2 . . ?
C17 C21 H21 107.2 . . ?
C22 C23 C24 110.5(4) . . ?
C22 C23 C21 112.6(4) . . ?
C24 C23 C21 109.6(3) . . ?
C22 C23 H23 108.0 . . ?
C24 C23 H23 108.0 . . ?
C21 C23 H23 108.0 . . ?
C25 C24 C23 114.8(4) . . ?
C25 C24 H24A 108.6 . . ?
C23 C24 H24A 108.6 . . ?
C25 C24 H24B 108.6 . . ?
C23 C24 H24B 108.6 . . ?
H24A C24 H24B 107.5 . . ?
C19 C20 C21 107.1(3) . . ?
C19 C20 H20A 110.3 . . ?
C21 C20 H20A 110.3 . . ?
C19 C20 H20B 110.3 . . ?
C21 C20 H20B 110.3 . . ?
H20A C20 H20B 108.6 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2 O1 C3 116.9(5) . . ?
C15 C14 C13 113.6(3) . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C20 C19 C18 104.2(3) . . ?
C20 C19 H19A 110.9 . . ?
C18 C19 H19A 110.9 . . ?
C20 C19 H19B 110.9 . . ?
C18 C19 H19B 110.9 . . ?
H19A C19 H19B 108.9 . . ?
C25 C26 C27 115.4(4) . . ?
C25 C26 H26A 108.4 . . ?
C27 C26 H26A 108.4 . . ?
C25 C26 H26B 108.4 . . ?
C27 C26 H26B 108.4 . . ?
H26A C26 H26B 107.5 . . ?
C26 C25 C24 113.0(4) . . ?
C26 C25 H25A 109.0 . . ?
C24 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
C24 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
C28 C27 C29 111.5(6) . . ?
C28 C27 C26 110.3(5) . . ?
C29 C27 C26 112.2(5) . . ?
C28 C27 H27 107.5 . . ?
C29 C27 H27 107.5 . . ?
C26 C27 H27 107.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C5 C4 C3 -171.8(4) . . . . ?
C9 C5 C4 C3 54.5(5) . . . . ?
Cl1 C5 C4 C3 -62.9(4) . . . . ?
C5 C4 C3 O1 -169.0(4) . . . . ?
C5 C4 C3 C8 -52.3(5) . . . . ?
C4 C5 C9 C7 -55.8(4) . . . . ?
C10 C5 C9 C7 171.2(3) . . . . ?
Cl1 C5 C9 C7 59.1(3) . . . . ?
C4 C5 C9 C6 62.0(4) . . . . ?
C10 C5 C9 C6 -71.0(4) . . . . ?
Cl1 C5 C9 C6 176.9(3) . . . . ?
C4 C5 C9 C13 -176.6(3) . . . . ?
C10 C5 C9 C13 50.4(4) . . . . ?
Cl1 C5 C9 C13 -61.7(3) . . . . ?
O1 C3 C8 C7 171.8(4) . . . . ?
C4 C3 C8 C7 52.8(5) . . . . ?
C14 C15 C17 C16 -66.6(4) . . . . ?
C14 C15 C17 C18 55.9(4) . . . . ?
C14 C15 C17 C21 166.1(3) . . . . ?
C11 C12 C18 C19 -55.1(4) . . . . ?
C13 C12 C18 C19 -177.1(3) . . . . ?
C11 C12 C18 C17 -178.0(3) . . . . ?
C13 C12 C18 C17 59.9(4) . . . . ?
C15 C17 C18 C12 -61.1(4) . . . . ?
C16 C17 C18 C12 60.3(4) . . . . ?
C21 C17 C18 C12 176.9(3) . . . . ?
C15 C17 C18 C19 168.1(3) . . . . ?
C16 C17 C18 C19 -70.5(4) . . . . ?
C21 C17 C18 C19 46.1(3) . . . . ?
C6 C9 C7 C8 -62.6(5) . . . . ?
C13 C9 C7 C8 175.8(4) . . . . ?
C5 C9 C7 C8 56.8(5) . . . . ?
C3 C8 C7 C9 -56.8(6) . . . . ?
C18 C12 C13 C14 -52.5(4) . . . . ?
C11 C12 C13 C14 -174.3(4) . . . . ?
C18 C12 C13 C9 179.8(3) . . . . ?
C11 C12 C13 C9 58.1(4) . . . . ?
C7 C9 C13 C14 58.9(5) . . . . ?
C6 C9 C13 C14 -61.3(4) . . . . ?
C5 C9 C13 C14 177.2(3) . . . . ?
C7 C9 C13 C12 -174.5(3) . . . . ?
C6 C9 C13 C12 65.4(4) . . . . ?
C5 C9 C13 C12 -56.2(4) . . . . ?
C18 C12 C11 C10 -172.7(3) . . . . ?
C13 C12 C11 C10 -52.0(5) . . . . ?
C12 C11 C10 C5 45.8(5) . . . . ?
C12 C11 C10 Cl2 -80.0(4) . . . . ?
C4 C5 C10 C11 -178.1(3) . . . . ?
C9 C5 C10 C11 -45.8(5) . . . . ?
Cl1 C5 C10 C11 70.8(4) . . . . ?
C4 C5 C10 Cl2 -53.3(4) . . . . ?
C9 C5 C10 Cl2 79.0(3) . . . . ?
Cl1 C5 C10 Cl2 -164.4(2) . . . . ?
C15 C17 C21 C23 79.5(4) . . . . ?
C16 C17 C21 C23 -48.0(5) . . . . ?
C18 C17 C21 C23 -166.3(3) . . . . ?
C15 C17 C21 C20 -155.0(3) . . . . ?
C16 C17 C21 C20 77.5(4) . . . . ?
C18 C17 C21 C20 -40.8(3) . . . . ?
C20 C21 C23 C22 -176.8(4) . . . . ?
C17 C21 C23 C22 -55.7(5) . . . . ?
C20 C21 C23 C24 59.8(5) . . . . ?
C17 C21 C23 C24 -179.1(3) . . . . ?
C22 C23 C24 C25 64.0(5) . . . . ?
C21 C23 C24 C25 -171.4(4) . . . . ?
C23 C21 C20 C19 150.9(3) . . . . ?
C17 C21 C20 C19 21.5(4) . . . . ?
O2 C2 O1 C3 3.6(10) . . . . ?
C1 C2 O1 C3 -179.5(6) . . . . ?
C8 C3 O1 C2 155.7(5) . . . . ?
C4 C3 O1 C2 -83.2(6) . . . . ?
C17 C15 C14 C13 -54.2(5) . . . . ?
C12 C13 C14 C15 51.2(5) . . . . ?
C9 C13 C14 C15 178.2(3) . . . . ?
C21 C20 C19 C18 7.1(4) . . . . ?
C12 C18 C19 C20 -161.0(3) . . . . ?
C17 C18 C19 C20 -33.3(4) . . . . ?
C27 C26 C25 C24 177.8(5) . . . . ?
C23 C24 C25 C26 177.3(4) . . . . ?
C25 C26 C27 C28 167.7(5) . . . . ?
C25 C26 C27 C29 -67.3(6) . . . . ?

_refine_diff_density_max         0.627
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.067


