# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2014


data_3ad

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 Cl O4'
_chemical_formula_sum            'C18 H17 Cl O4'
_chemical_formula_weight         332.77
_chemical_absolute_configuration ad

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           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   6.6348(9)
_cell_length_b                   11.6431(15)
_cell_length_c                   10.7797(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.155(8)
_cell_angle_gamma                90.00
_cell_volume                     822.12(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 0.3
_diffrn_reflns_number            17575
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_sigmaI/netI    0.0489
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         30.58
_reflns_number_total             4329
_reflns_number_gt                2853
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker smart apex ccd'
_computing_cell_refinement       'Bruker smart apex ccd'
_computing_data_reduction        'Bruker saint'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ortep-III
_computing_publication_material  WinGXv1.80.05

_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)+(0.0373P)²+0.0220P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_number_reflns         4329
_refine_ls_number_parameters     210
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0906
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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 -0.51631(9) -0.68792(6) -0.40046(5) 0.07230(19) Uani 1 1 d . . .
O1 O -0.3729(3) -0.93074(14) 0.22371(18) 0.0873(6) Uani 1 1 d . . .
O2 O -0.5691(2) -0.77873(11) 0.16510(13) 0.0495(3) Uani 1 1 d . . .
O3 O -0.9596(2) -0.60277(15) -0.01327(19) 0.0772(5) Uani 1 1 d . . .
O4 O -0.4917(2) -0.85370(11) -0.14840(14) 0.0548(4) Uani 1 1 d . . .
C1 C -0.3905(4) -0.8284(2) 0.2173(2) 0.0590(6) Uani 1 1 d . . .
C2 C -0.5481(3) -0.65412(15) 0.16857(18) 0.0461(5) Uani 1 1 d . . .
C3 C -0.5904(3) -0.61167(15) 0.03160(17) 0.0387(4) Uani 1 1 d . . .
H3 H -0.5777 -0.5279 0.0297 0.046 Uiso 1 1 calc R . .
C4 C -0.8034(3) -0.64721(14) -0.03228(19) 0.0431(4) Uani 1 1 d . . .
C5 C -0.7932(3) -0.74628(14) -0.12262(18) 0.0391(4) Uani 1 1 d . . .
C6 C -0.8843(3) -0.70211(16) -0.25678(19) 0.0473(4) Uani 1 1 d . . .
H6A H -1.0265 -0.6822 -0.2577 0.057 Uiso 1 1 calc R . .
H6B H -0.8129 -0.6326 -0.2737 0.057 Uiso 1 1 calc R . .
C7 C -0.8714(3) -0.78665(18) -0.36029(19) 0.0476(4) Uani 1 1 d . . .
C8 C -1.0266(4) -0.8677(2) -0.3938(2) 0.0638(6) Uani 1 1 d . . .
H8 H -1.1388 -0.8673 -0.3519 0.077 Uiso 1 1 calc R . .
C9 C -1.0187(5) -0.9474(2) -0.4861(3) 0.0800(8) Uani 1 1 d . . .
H9 H -1.1247 -0.9997 -0.5066 0.096 Uiso 1 1 calc R . .
C10 C -0.8550(6) -0.9499(3) -0.5481(3) 0.0901(9) Uani 1 1 d . . .
H10 H -0.8484 -1.0052 -0.6096 0.108 Uiso 1 1 calc R . .
C11 C -0.6995(5) -0.8714(2) -0.5203(2) 0.0754(7) Uani 1 1 d . . .
H11 H -0.5884 -0.8727 -0.5631 0.091 Uiso 1 1 calc R . .
C12 C -0.7107(3) -0.79025(18) -0.4276(2) 0.0541(5) Uani 1 1 d . . .
C13 C -0.5659(3) -0.76765(14) -0.11267(16) 0.0371(4) Uani 1 1 d . . .
C14 C -0.4509(3) -0.66601(17) -0.05262(18) 0.0425(4) Uani 1 1 d . . .
H14A H -0.4223 -0.6118 -0.1160 0.051 Uiso 1 1 calc R . .
H14B H -0.3227 -0.6899 -0.0032 0.051 Uiso 1 1 calc R . .
C15 C -0.9070(3) -0.85125(16) -0.0843(2) 0.0522(5) Uani 1 1 d . . .
H15A H -0.8549 -0.8709 0.0013 0.078 Uiso 1 1 calc R . .
H15B H -0.8876 -0.9147 -0.1380 0.078 Uiso 1 1 calc R . .
H15C H -1.0499 -0.8341 -0.0920 0.078 Uiso 1 1 calc R . .
C16 C -0.3340(4) -0.63881(19) 0.2303(2) 0.0637(6) Uani 1 1 d . . .
H16 H -0.2704 -0.5680 0.2463 0.076 Uiso 1 1 calc R . .
C17 C -0.2467(4) -0.7371(2) 0.2592(3) 0.0713(7) Uani 1 1 d . . .
H17 H -0.1135 -0.7473 0.3001 0.086 Uiso 1 1 calc R . .
C18 C -0.6975(4) -0.6046(2) 0.2477(2) 0.0765(8) Uani 1 1 d . . .
H18A H -0.6712 -0.6372 0.3305 0.115 Uiso 1 1 calc R . .
H18B H -0.8345 -0.6227 0.2094 0.115 Uiso 1 1 calc R . .
H18C H -0.6812 -0.5228 0.2531 0.115 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 C12 1.746(2) . ?
O1 C1 1.199(2) . ?
O2 C1 1.357(3) . ?
O2 C2 1.457(2) . ?
O3 C4 1.205(2) . ?
O4 C13 1.206(2) . ?
C1 C17 1.452(3) . ?
C2 C16 1.480(3) . ?
C2 C18 1.520(3) . ?
C2 C3 1.540(3) . ?
C3 C4 1.527(3) . ?
C3 C14 1.533(2) . ?
C3 H3 0.9800 . ?
C4 C5 1.518(2) . ?
C5 C13 1.515(3) . ?
C5 C15 1.528(2) . ?
C5 C6 1.563(3) . ?
C6 C7 1.501(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C12 1.382(3) . ?
C7 C8 1.402(3) . ?
C8 C9 1.367(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.363(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(3) . ?
C11 H11 0.9300 . ?
C13 C14 1.498(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.298(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C1 O2 C2 109.85(16) . . ?
O1 C1 O2 121.2(2) . . ?
O1 C1 C17 131.1(2) . . ?
O2 C1 C17 107.73(19) . . ?
O2 C2 C16 102.27(15) . . ?
O2 C2 C18 108.87(17) . . ?
C16 C2 C18 111.52(19) . . ?
O2 C2 C3 107.03(15) . . ?
C16 C2 C3 114.07(15) . . ?
C18 C2 C3 112.37(17) . . ?
C4 C3 C14 102.94(14) . . ?
C4 C3 C2 111.08(15) . . ?
C14 C3 C2 113.60(15) . . ?
C4 C3 H3 109.7 . . ?
C14 C3 H3 109.7 . . ?
C2 C3 H3 109.7 . . ?
O3 C4 C5 124.25(18) . . ?
O3 C4 C3 124.49(17) . . ?
C5 C4 C3 111.26(14) . . ?
C13 C5 C4 102.99(15) . . ?
C13 C5 C15 112.24(15) . . ?
C4 C5 C15 111.10(15) . . ?
C13 C5 C6 110.71(14) . . ?
C4 C5 C6 107.06(14) . . ?
C15 C5 C6 112.24(16) . . ?
C7 C6 C5 114.37(15) . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C12 C7 C8 116.1(2) . . ?
C12 C7 C6 123.41(19) . . ?
C8 C7 C6 120.44(19) . . ?
C9 C8 C7 122.2(2) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.5(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 119.1(3) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C7 C12 C11 122.2(2) . . ?
C7 C12 Cl1 120.12(17) . . ?
C11 C12 Cl1 117.61(19) . . ?
O4 C13 C14 126.02(16) . . ?
O4 C13 C5 124.48(17) . . ?
C14 C13 C5 109.50(14) . . ?
C13 C14 C3 105.52(13) . . ?
C13 C14 H14A 110.6 . . ?
C3 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
C3 C14 H14B 110.6 . . ?
H14A C14 H14B 108.8 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C2 111.20(19) . . ?
C17 C16 H16 124.4 . . ?
C2 C16 H16 124.4 . . ?
C16 C17 C1 108.9(2) . . ?
C16 C17 H17 125.5 . . ?
C1 C17 H17 125.5 . . ?
C2 C18 H18A 109.5 . . ?
C2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.58
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.032
_database_code_depnum_ccdc_archive 'CCDC 965956'

data_5

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 O2'
_chemical_formula_sum            'C17 H18 O2'
_chemical_formula_weight         254.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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           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                   6.569(8)
_cell_length_b                   13.286(17)
_cell_length_c                   17.05(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1489(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3722
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      20.16


_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   sadabs
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         '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 18.4
_diffrn_reflns_number            19145
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.943
_diffrn_reflns_theta_max         25.980
_diffrn_reflns_theta_full        25.242

_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 1.001
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998

_reflns_number_total             2919
_reflns_number_gt                2097
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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-97 (Sheldrick, 2008)'
_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)+(0.1000P)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 
;
 Flack x determined using 709 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(8)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2919
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1392
_refine_ls_wR_factor_gt          0.1209
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_restrained_S_all      0.909
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.2943(5) 2.1054(3) 1.8264(2) 0.0776(9) Uani 1 1 d . . . . .
H1 H 1.3669 2.1034 1.7796 0.093 Uiso 1 1 calc R U . . .
O2 O 1.3862(3) 1.92692(19) 1.68085(15) 0.0839(8) Uani 1 1 d . . . . .
C2 C 1.2759(9) 2.1513(3) 1.9611(3) 0.1139(19) Uani 1 1 d . . . . .
H2 H 1.3324 2.1817 2.0052 0.137 Uiso 1 1 calc R U . . .
C3 C 1.3817(8) 2.1494(3) 1.8914(3) 0.1051(15) Uani 1 1 d . . . . .
H3 H 1.5111 2.1775 1.8882 0.126 Uiso 1 1 calc R U . . .
C4 C 1.0977(5) 2.0636(2) 1.82916(18) 0.0576(7) Uani 1 1 d . . . . .
C5 C 0.9998(5) 2.0192(2) 1.75720(16) 0.0604(7) Uani 1 1 d . . . . .
H5A H 1.0407 2.0590 1.7122 0.073 Uiso 1 1 calc R U . . .
H5B H 0.8534 2.0258 1.7625 0.073 Uiso 1 1 calc R U . . .
C6 C 1.0495(4) 1.9059(2) 1.73927(15) 0.0506(7) Uani 1 1 d . . . . .
C7 C 0.9971(4) 1.8358(2) 1.80732(15) 0.0472(6) Uani 1 1 d . . . . .
C8 C 1.1851(3) 1.77773(18) 1.83240(13) 0.0424(6) Uani 1 1 d . . . . .
C9 C 1.1951(4) 1.69945(18) 1.89372(14) 0.0466(6) Uani 1 1 d . . . . .
C10 C 1.0318(5) 1.6797(2) 1.93829(15) 0.0556(7) Uani 1 1 d . . . . .
H10 H 0.9162 1.7186 1.9297 0.067 Uiso 1 1 calc R U . . .
C11 C 1.0192(6) 1.6001(3) 2.00106(19) 0.0800(10) Uani 1 1 d . . . . .
H11A H 1.0089 1.6318 2.0515 0.120 Uiso 1 1 calc R U . . .
H11B H 1.1393 1.5590 1.9994 0.120 Uiso 1 1 calc R U . . .
H11C H 0.9014 1.5589 1.9922 0.120 Uiso 1 1 calc R U . . .
C12 C 1.0879(10) 2.1084(3) 1.9651(2) 0.1060(15) Uani 1 1 d . . . . .
H12 H 1.0186 2.1083 2.0126 0.127 Uiso 1 1 calc R U . . .
C13 C 0.9973(7) 2.0647(3) 1.89980(19) 0.0776(10) Uani 1 1 d . . . . .
H13 H 0.8684 2.0362 1.9039 0.093 Uiso 1 1 calc R U . . .
C14 C 1.2775(4) 1.8866(2) 1.72985(16) 0.0560(7) Uani 1 1 d . . . . .
C15 C 1.3407(4) 1.8095(2) 1.78662(16) 0.0537(7) Uani 1 1 d . . . . .
H15 H 1.4731 1.7852 1.7907 0.064 Uiso 1 1 calc R U . . .
C16 C 1.3958(5) 1.6442(3) 1.9033(2) 0.0702(9) Uani 1 1 d . . . . .
H16A H 1.5060 1.6916 1.9011 0.105 Uiso 1 1 calc R U . . .
H16B H 1.4107 1.5958 1.8620 0.105 Uiso 1 1 calc R U . . .
H16C H 1.3976 1.6102 1.9530 0.105 Uiso 1 1 calc R U . . .
O16 O 0.8259(3) 1.82823(18) 1.83450(13) 0.0763(7) Uani 1 1 d . . . . .
C17 C 0.9323(5) 1.8717(3) 1.66585(17) 0.0692(8) Uani 1 1 d . . . . .
H17A H 0.9628 1.9161 1.6230 0.104 Uiso 1 1 calc R U . . .
H17B H 0.7887 1.8733 1.6764 0.104 Uiso 1 1 calc R U . . .
H17C H 0.9722 1.8044 1.6524 0.104 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 1.379(6) . ?
C1 C4 1.407(5) . ?
C1 H1 0.9300 . ?
O2 C14 1.222(4) . ?
C2 C12 1.362(7) . ?
C2 C3 1.378(7) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C13 1.373(5) . ?
C4 C5 1.506(4) . ?
C5 C6 1.570(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.527(4) . ?
C6 C14 1.528(5) . ?
C6 C17 1.539(4) . ?
C7 O16 1.221(3) . ?
C7 C8 1.518(4) . ?
C8 C15 1.354(4) . ?
C8 C9 1.476(4) . ?
C9 C10 1.340(4) . ?
C9 C16 1.518(4) . ?
C10 C11 1.507(4) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.389(6) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.470(4) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C3 C1 C4 121.5(4) . . ?
C3 C1 H1 119.3 . . ?
C4 C1 H1 119.3 . . ?
C12 C2 C3 119.5(4) . . ?
C12 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C1 119.5(5) . . ?
C2 C3 H3 120.3 . . ?
C1 C3 H3 120.3 . . ?
C13 C4 C1 117.8(3) . . ?
C13 C4 C5 120.9(3) . . ?
C1 C4 C5 121.3(3) . . ?
C4 C5 C6 116.5(2) . . ?
C4 C5 H5A 108.2 . . ?
C6 C5 H5A 108.2 . . ?
C4 C5 H5B 108.2 . . ?
C6 C5 H5B 108.2 . . ?
H5A C5 H5B 107.3 . . ?
C7 C6 C14 101.5(2) . . ?
C7 C6 C17 109.0(2) . . ?
C14 C6 C17 110.8(3) . . ?
C7 C6 C5 112.9(2) . . ?
C14 C6 C5 112.6(2) . . ?
C17 C6 C5 109.7(2) . . ?
O16 C7 C8 126.9(2) . . ?
O16 C7 C6 123.1(2) . . ?
C8 C7 C6 109.9(2) . . ?
C15 C8 C9 126.5(2) . . ?
C15 C8 C7 107.1(2) . . ?
C9 C8 C7 126.4(2) . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 C16 122.6(3) . . ?
C8 C9 C16 117.1(2) . . ?
C9 C10 C11 125.7(3) . . ?
C9 C10 H10 117.1 . . ?
C11 C10 H10 117.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C12 C13 121.6(4) . . ?
C2 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C4 C13 C12 120.1(4) . . ?
C4 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
O2 C14 C15 126.2(3) . . ?
O2 C14 C6 124.8(3) . . ?
C15 C14 C6 108.9(2) . . ?
C8 C15 C14 112.6(3) . . ?
C8 C15 H15 123.7 . . ?
C14 C15 H15 123.7 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C6 C17 H17A 109.5 . . ?
C6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C12 C2 C3 C1 1.0(6) . . . . ?
C4 C1 C3 C2 0.9(6) . . . . ?
C3 C1 C4 C13 -2.2(5) . . . . ?
C3 C1 C4 C5 177.7(3) . . . . ?
C13 C4 C5 C6 -93.9(4) . . . . ?
C1 C4 C5 C6 86.2(3) . . . . ?
C4 C5 C6 C7 56.3(3) . . . . ?
C4 C5 C6 C14 -57.9(3) . . . . ?
C4 C5 C6 C17 178.1(3) . . . . ?
C14 C6 C7 O16 179.6(3) . . . . ?
C17 C6 C7 O16 -63.4(4) . . . . ?
C5 C6 C7 O16 58.8(4) . . . . ?
C14 C6 C7 C8 -2.0(3) . . . . ?
C17 C6 C7 C8 115.0(3) . . . . ?
C5 C6 C7 C8 -122.8(2) . . . . ?
O16 C7 C8 C15 179.8(3) . . . . ?
C6 C7 C8 C15 1.4(3) . . . . ?
O16 C7 C8 C9 1.2(4) . . . . ?
C6 C7 C8 C9 -177.1(2) . . . . ?
C15 C8 C9 C10 175.7(3) . . . . ?
C7 C8 C9 C10 -6.0(4) . . . . ?
C15 C8 C9 C16 -4.1(4) . . . . ?
C7 C8 C9 C16 174.2(2) . . . . ?
C8 C9 C10 C11 178.1(3) . . . . ?
C16 C9 C10 C11 -2.1(5) . . . . ?
C3 C2 C12 C13 -1.7(6) . . . . ?
C1 C4 C13 C12 1.6(5) . . . . ?
C5 C4 C13 C12 -178.3(3) . . . . ?
C2 C12 C13 C4 0.3(6) . . . . ?
C7 C6 C14 O2 179.5(3) . . . . ?
C17 C6 C14 O2 63.9(4) . . . . ?
C5 C6 C14 O2 -59.5(4) . . . . ?
C7 C6 C14 C15 1.9(3) . . . . ?
C17 C6 C14 C15 -113.8(3) . . . . ?
C5 C6 C14 C15 122.9(3) . . . . ?
C9 C8 C15 C14 178.4(2) . . . . ?
C7 C8 C15 C14 -0.2(3) . . . . ?
O2 C14 C15 C8 -178.8(3) . . . . ?
C6 C14 C15 C8 -1.2(3) . . . . ?

_refine_diff_density_max         0.125
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.038

_shelxl_version_number           2013-2



_database_code_depnum_ccdc_archive 'CCDC 965957'
data_6
_audit_creation_date             2013-05-22
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_publ_contact_author_address     ?
_publ_contact_author_email       ?
_publ_contact_author_phone       ?
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C18 H15 Cl O4)'
_chemical_formula_sum            'C36 H30 Cl2 O8'
_chemical_formula_weight         661.50
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'

_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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   6.465(5)
_cell_length_b                   16.927(5)
_cell_length_c                   29.143(5)
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                90.000
_cell_volume                     3189(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    100
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.9409
_exptl_absorpt_correction_T_min  0.9315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            49790
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.39
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_reflns_number_gt                5028
_reflns_number_total             5631
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.048
_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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)+(0.0385P)²+1.1946P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom


# Permitted for _refine_ls_hydrogen_treatment :
# refall  - refined all H parameters
# refxyz  - refined H coordinates only
# refU    - refined H U only
# noref   - no refinement of H parameters
# constr  - H parameters constrained
# mixed   - some constrained, some independent
# undef   - H-atom parameters not defined
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(6)

# Permitted for _chemical_absolute_configuration:
# Absolute configuration details
# rm   = Det. by chiral ref. mol. with known abs.conf
# ad   = Det. by anomalous dispersion
# rmad = Det. by 'rm' and 'ad'
# syn  = Det. with reference to synthesis
# unk  = Unknown/Arbitrary

_refine_ls_number_reflns         5631
_refine_ls_number_parameters     419
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0913
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.5815(4) 0.65297(16) 0.54443(9) 0.0235(6) Uani 1 1 d . . .
C2 C 0.6468(4) 0.67467(15) 0.50085(9) 0.0248(6) Uani 1 1 d . . .
H2 H 0.7825 0.6947 0.4963 0.030 Uiso 1 1 calc R . .
C3 C 0.5138(4) 0.66702(14) 0.46430(9) 0.0211(6) Uani 1 1 d . . .
H3 H 0.5590 0.6819 0.4345 0.025 Uiso 1 1 calc R . .
C4 C 0.3126(4) 0.63770(14) 0.47014(8) 0.0195(6) Uani 1 1 d . . .
C5 C 0.2495(4) 0.61943(15) 0.51455(9) 0.0226(6) Uani 1 1 d . . .
H5 H 0.1121 0.6015 0.5195 0.027 Uiso 1 1 calc R . .
C6 C 0.3808(4) 0.62664(15) 0.55159(9) 0.0236(6) Uani 1 1 d . . .
H6 H 0.3345 0.6138 0.5816 0.028 Uiso 1 1 calc R . .
C7 C 0.1787(4) 0.62015(15) 0.42911(8) 0.0214(6) Uani 1 1 d . . .
H7A H 0.2075 0.6596 0.4049 0.026 Uiso 1 1 calc R . .
H7B H 0.0316 0.6256 0.4380 0.026 Uiso 1 1 calc R . .
C8 C 0.2143(4) 0.53601(14) 0.40925(8) 0.0165(5) Uani 1 1 d . . .
C9 C 0.0804(4) 0.52097(17) 0.36695(9) 0.0236(6) Uani 1 1 d . . .
H9A H 0.1198 0.5578 0.3425 0.035 Uiso 1 1 calc R . .
H9B H -0.0655 0.5289 0.3748 0.035 Uiso 1 1 calc R . .
H9C H 0.1010 0.4666 0.3564 0.035 Uiso 1 1 calc R . .
C10 C 0.4437(4) 0.52492(15) 0.39940(8) 0.0163(5) Uani 1 1 d . . .
C11 C 0.5344(4) 0.47393(15) 0.43500(8) 0.0162(5) Uani 1 1 d . . .
H11 H 0.6782 0.4640 0.4386 0.019 Uiso 1 1 calc R . .
C12 C 0.3862(4) 0.44355(14) 0.46160(8) 0.0145(5) Uani 1 1 d . . .
C13 C 0.1809(4) 0.47578(15) 0.44722(8) 0.0182(5) Uani 1 1 d . . .
C14 C 0.4083(4) 0.38550(15) 0.50046(8) 0.0150(5) Uani 1 1 d . . .
C15 C 0.2954(4) 0.30895(15) 0.48965(9) 0.0207(6) Uani 1 1 d . . .
H15A H 0.3432 0.2884 0.4601 0.031 Uiso 1 1 calc R . .
H15B H 0.1463 0.3190 0.4882 0.031 Uiso 1 1 calc R . .
H15C H 0.3239 0.2701 0.5138 0.031 Uiso 1 1 calc R . .
C16 C 0.3485(4) 0.42009(15) 0.54618(8) 0.0180(6) Uani 1 1 d . . .
H16 H 0.2138 0.4380 0.5540 0.022 Uiso 1 1 calc R . .
C17 C 0.5100(4) 0.42196(15) 0.57382(9) 0.0201(6) Uani 1 1 d . . .
H17 H 0.5102 0.4408 0.6045 0.024 Uiso 1 1 calc R . .
C18 C 0.6893(4) 0.38998(15) 0.54912(8) 0.0185(6) Uani 1 1 d . . .
C19 C 0.8214(4) 0.23445(16) 0.81257(9) 0.0230(6) Uani 1 1 d . . .
C20 C 0.7487(5) 0.17723(15) 0.78322(9) 0.0238(6) Uani 1 1 d . . .
H20 H 0.6174 0.1536 0.7883 0.029 Uiso 1 1 calc R . .
C21 C 0.8690(4) 0.15446(16) 0.74625(9) 0.0237(6) Uani 1 1 d . . .
H21 H 0.8183 0.1155 0.7257 0.028 Uiso 1 1 calc R . .
C22 C 1.0626(4) 0.18760(16) 0.73866(9) 0.0221(6) Uani 1 1 d . . .
C23 C 1.1365(4) 0.24188(16) 0.77044(9) 0.0242(6) Uani 1 1 d . . .
H23 H 1.2719 0.2627 0.7667 0.029 Uiso 1 1 calc R . .
C24 C 1.0173(4) 0.26653(17) 0.80762(9) 0.0258(6) Uani 1 1 d . . .
H24 H 1.0687 0.3042 0.8289 0.031 Uiso 1 1 calc R . .
C25 C 1.1791(4) 0.17123(15) 0.69466(9) 0.0240(6) Uani 1 1 d . . .
H25A H 1.1498 0.1166 0.6845 0.029 Uiso 1 1 calc R . .
H25B H 1.3295 0.1755 0.7005 0.029 Uiso 1 1 calc R . .
C26 C 1.1175(4) 0.22965(16) 0.65610(9) 0.0203(6) Uani 1 1 d . . .
C27 C 1.2386(5) 0.21332(17) 0.61193(9) 0.0277(7) Uani 1 1 d . . .
H27A H 1.2079 0.1598 0.6011 0.042 Uiso 1 1 calc R . .
H27B H 1.3872 0.2181 0.6180 0.042 Uiso 1 1 calc R . .
H27C H 1.1983 0.2516 0.5884 0.042 Uiso 1 1 calc R . .
C28 C 0.8843(4) 0.22730(16) 0.64800(8) 0.0194(6) Uani 1 1 d . . .
C29 C 0.7951(4) 0.30402(15) 0.66131(8) 0.0185(6) Uani 1 1 d . . .
H29 H 0.6515 0.3159 0.6610 0.022 Uiso 1 1 calc R . .
C30 C 0.9432(4) 0.35466(16) 0.67395(8) 0.0181(6) Uani 1 1 d . . .
C31 C 1.1481(4) 0.31485(16) 0.67158(8) 0.0208(6) Uani 1 1 d . . .
C32 C 0.9200(4) 0.43873(15) 0.68947(9) 0.0191(6) Uani 1 1 d . . .
C33 C 1.0376(5) 0.49676(16) 0.65917(9) 0.0241(6) Uani 1 1 d . . .
H33A H 0.9949 0.4898 0.6272 0.036 Uiso 1 1 calc R . .
H33B H 1.1865 0.4869 0.6619 0.036 Uiso 1 1 calc R . .
H33C H 1.0071 0.5509 0.6690 0.036 Uiso 1 1 calc R . .
C34 C 0.9717(4) 0.44558(15) 0.73957(9) 0.0192(6) Uani 1 1 d . . .
H34 H 1.1051 0.4369 0.7523 0.023 Uiso 1 1 calc R . .
C35 C 0.8071(4) 0.46513(15) 0.76337(9) 0.0223(6) Uani 1 1 d . . .
H35 H 0.8011 0.4705 0.7958 0.027 Uiso 1 1 calc R . .
C36 C 0.6338(4) 0.47725(15) 0.73158(9) 0.0227(6) Uani 1 1 d . . .
O1 O 0.0156(3) 0.45771(12) 0.46386(6) 0.0271(5) Uani 1 1 d . . .
O2 O 0.5360(3) 0.55397(11) 0.36693(6) 0.0223(4) Uani 1 1 d . . .
O3 O 0.6279(3) 0.36904(10) 0.50598(5) 0.0163(4) Uani 1 1 d . . .
O4 O 0.8648(3) 0.37936(12) 0.56180(6) 0.0253(4) Uani 1 1 d . . .
O5 O 0.7903(3) 0.17079(10) 0.63266(6) 0.0250(4) Uani 1 1 d . . .
O6 O 1.3128(3) 0.34534(12) 0.68070(6) 0.0279(4) Uani 1 1 d . . .
O7 O 0.7020(3) 0.45968(10) 0.68793(6) 0.0202(4) Uani 1 1 d . . .
O8 O 0.4604(3) 0.49931(12) 0.73841(7) 0.0313(5) Uani 1 1 d . . .
Cl1 Cl 0.75396(11) 0.65767(4) 0.59021(2) 0.03282(18) Uani 1 1 d . . .
Cl2 Cl 0.66479(12) 0.26823(5) 0.85711(2) 0.03472(19) 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 1.388(4) . ?
C1 C6 1.388(4) . ?
C1 Cl1 1.741(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.375(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.403(4) . ?
C4 C5 1.392(4) . ?
C4 C7 1.506(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.378(4) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.554(4) . ?
C8 C9 1.528(4) . ?
C8 C10 1.522(4) . ?
C8 C13 1.520(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.472(4) . ?
C10 O2 1.222(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.336(4) . ?
C12 C13 1.494(4) . ?
C12 C14 1.506(3) . ?
C13 O1 1.213(3) . ?
C14 C15 1.520(4) . ?
C14 C16 1.506(3) . ?
C14 O3 1.455(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 0.9500 . ?
C16 C17 1.319(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.468(4) . ?
C18 O3 1.365(3) . ?
C18 O4 1.207(3) . ?
C19 C20 1.375(4) . ?
C19 C24 1.385(4) . ?
C19 Cl2 1.743(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.383(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.389(4) . ?
C22 C23 1.389(4) . ?
C22 C25 1.513(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.394(4) . ?
C24 H24 0.9500 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.549(4) . ?
C26 C27 1.532(4) . ?
C26 C28 1.527(4) . ?
C26 C31 1.524(4) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.473(4) . ?
C28 O5 1.218(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.337(4) . ?
C30 C31 1.488(4) . ?
C30 C32 1.501(4) . ?
C31 O6 1.213(3) . ?
C32 C33 1.524(4) . ?
C32 C34 1.502(4) . ?
C32 O7 1.454(3) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34 0.9500 . ?
C34 C35 1.312(4) . ?
C35 H35 0.9500 . ?
C35 C36 1.468(4) . ?
C36 O7 1.379(3) . ?
C36 O8 1.198(3) . ?

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 Cl1 119.6(2) . . ?
C6 C1 C2 120.5(3) . . ?
C6 C1 Cl1 119.9(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.3(2) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C7 120.4(2) . . ?
C5 C4 C3 117.6(2) . . ?
C5 C4 C7 121.8(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.9(3) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 H6 120.5 . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 H6 120.5 . . ?
C4 C7 H7A 109.0 . . ?
C4 C7 H7B 109.0 . . ?
C4 C7 C8 113.0(2) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C9 C8 C7 111.7(2) . . ?
C10 C8 C7 109.1(2) . . ?
C10 C8 C9 112.3(2) . . ?
C13 C8 C7 108.8(2) . . ?
C13 C8 C9 113.3(2) . . ?
C13 C8 C10 101.1(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C8 109.1(2) . . ?
O2 C10 C8 124.9(2) . . ?
O2 C10 C11 126.0(2) . . ?
C10 C11 H11 124.8 . . ?
C12 C11 C10 110.4(2) . . ?
C12 C11 H11 124.8 . . ?
C11 C12 C13 109.5(2) . . ?
C11 C12 C14 128.3(2) . . ?
C13 C12 C14 122.2(2) . . ?
C12 C13 C8 108.8(2) . . ?
O1 C13 C8 125.8(2) . . ?
O1 C13 C12 125.3(2) . . ?
C12 C14 C15 110.8(2) . . ?
C16 C14 C12 112.8(2) . . ?
C16 C14 C15 113.0(2) . . ?
O3 C14 C12 107.51(19) . . ?
O3 C14 C15 109.2(2) . . ?
O3 C14 C16 103.13(19) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16 124.9 . . ?
C17 C16 C14 110.3(2) . . ?
C17 C16 H16 124.9 . . ?
C16 C17 H17 125.8 . . ?
C16 C17 C18 108.5(2) . . ?
C18 C17 H17 125.8 . . ?
O3 C18 C17 108.5(2) . . ?
O4 C18 C17 130.3(2) . . ?
O4 C18 O3 121.1(2) . . ?
C20 C19 C24 121.6(3) . . ?
C20 C19 Cl2 119.7(2) . . ?
C24 C19 Cl2 118.7(2) . . ?
C19 C20 H20 120.4 . . ?
C19 C20 C21 119.2(3) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 119.4 . . ?
C20 C21 C22 121.2(3) . . ?
C22 C21 H21 119.4 . . ?
C21 C22 C23 118.1(3) . . ?
C21 C22 C25 120.6(3) . . ?
C23 C22 C25 121.0(2) . . ?
C22 C23 H23 119.1 . . ?
C22 C23 C24 121.7(3) . . ?
C24 C23 H23 119.1 . . ?
C19 C24 C23 118.0(3) . . ?
C19 C24 H24 121.0 . . ?
C23 C24 H24 121.0 . . ?
C22 C25 H25A 109.3 . . ?
C22 C25 H25B 109.3 . . ?
C22 C25 C26 111.7(2) . . ?
H25A C25 H25B 107.9 . . ?
C26 C25 H25A 109.3 . . ?
C26 C25 H25B 109.3 . . ?
C27 C26 C25 111.3(2) . . ?
C28 C26 C25 110.4(2) . . ?
C28 C26 C27 111.7(2) . . ?
C31 C26 C25 110.9(2) . . ?
C31 C26 C27 110.7(2) . . ?
C31 C26 C28 101.4(2) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C26 108.9(2) . . ?
O5 C28 C26 124.7(2) . . ?
O5 C28 C29 126.4(3) . . ?
C28 C29 H29 124.5 . . ?
C30 C29 C28 110.9(2) . . ?
C30 C29 H29 124.5 . . ?
C29 C30 C31 109.5(2) . . ?
C29 C30 C32 128.3(2) . . ?
C31 C30 C32 122.2(2) . . ?
C30 C31 C26 109.1(2) . . ?
O6 C31 C26 125.5(3) . . ?
O6 C31 C30 125.4(2) . . ?
C30 C32 C33 112.8(2) . . ?
C30 C32 C34 110.1(2) . . ?
C34 C32 C33 113.7(2) . . ?
O7 C32 C30 108.6(2) . . ?
O7 C32 C33 108.0(2) . . ?
O7 C32 C34 103.1(2) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 H34 124.7 . . ?
C35 C34 C32 110.7(2) . . ?
C35 C34 H34 124.7 . . ?
C34 C35 H35 125.7 . . ?
C34 C35 C36 108.7(2) . . ?
C36 C35 H35 125.7 . . ?
O7 C36 C35 107.9(2) . . ?
O8 C36 C35 130.7(3) . . ?
O8 C36 O7 121.3(2) . . ?
C18 O3 C14 109.61(19) . . ?
C36 O7 C32 109.5(2) . . ?

_database_code_depnum_ccdc_archive 'CCDC 965958'
