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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ja
_database_code_depnum_ccdc_archive 'CCDC 1508097'
_audit_update_record             
;
2016-10-04 deposited with the CCDC.
2017-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 Cl O4'
_chemical_formula_weight         380.81

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'
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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   9.3404(10)
_cell_length_b                   11.2518(11)
_cell_length_c                   16.982(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1784.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3132
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      25.01

_exptl_crystal_description       BAR
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8539
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3132
_reflns_number_gt                2753
_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)+(0.0359P)²+0.1983P] 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   -0.08(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3132
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0723
_refine_ls_wR_factor_gt          0.0686
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 -0.07836(7) 0.98174(5) -0.41294(3) 0.06392(18) Uani 1 1 d . . .
O1 O -0.48546(14) 1.17334(11) -0.16226(8) 0.0442(3) Uani 1 1 d . . .
O2 O -0.2774(2) 1.26136(15) 0.00676(9) 0.0688(5) Uani 1 1 d . . .
O3 O -0.11183(15) 0.92550(12) -0.07303(9) 0.0550(4) Uani 1 1 d . . .
O4 O -0.33124(14) 0.85580(11) -0.07865(8) 0.0467(4) Uani 1 1 d . . .
C1 C -0.5292(2) 0.97879(17) -0.11864(10) 0.0368(4) Uani 1 1 d . . .
C2 C -0.6766(2) 0.9888(2) -0.13027(12) 0.0508(5) Uani 1 1 d . . .
H2 H -0.7155 1.0594 -0.1489 0.061 Uiso 1 1 calc R . .
C3 C -0.7643(2) 0.8929(2) -0.11396(15) 0.0629(7) Uani 1 1 d . . .
H3 H -0.8624 0.8990 -0.1226 0.075 Uiso 1 1 calc R . .
C4 C -0.7087(3) 0.7896(2) -0.08533(15) 0.0655(7) Uani 1 1 d . . .
H4 H -0.7696 0.7264 -0.0740 0.079 Uiso 1 1 calc R . .
C5 C -0.5641(3) 0.77728(19) -0.07293(13) 0.0553(6) Uani 1 1 d . . .
H5 H -0.5266 0.7068 -0.0530 0.066 Uiso 1 1 calc R . .
C6 C -0.4757(2) 0.87196(17) -0.09072(12) 0.0403(5) Uani 1 1 d . . .
C7 C -0.4277(2) 1.07223(15) -0.13500(10) 0.0340(4) Uani 1 1 d . . .
C8 C -0.28606(19) 1.05747(15) -0.12132(10) 0.0337(4) Uani 1 1 d . . .
C9 C -0.2339(2) 0.94653(16) -0.09022(12) 0.0390(4) Uani 1 1 d . . .
C10 C -0.17924(19) 1.15598(15) -0.13208(11) 0.0355(4) Uani 1 1 d . . .
H10 H -0.1169 1.1564 -0.0856 0.043 Uiso 1 1 calc R . .
C11 C -0.0835(2) 1.14337(15) -0.20434(11) 0.0369(4) Uani 1 1 d . . .
C12 C -0.1188(2) 1.07343(17) -0.26802(11) 0.0393(4) Uani 1 1 d . . .
H12 H -0.2015 1.0275 -0.2668 0.047 Uiso 1 1 calc R . .
C13 C -0.0316(2) 1.07124(17) -0.33375(11) 0.0441(5) Uani 1 1 d . . .
C14 C 0.0900(2) 1.13904(19) -0.33797(14) 0.0573(6) Uani 1 1 d . . .
H14 H 0.1460 1.1394 -0.3833 0.069 Uiso 1 1 calc R . .
C15 C 0.1274(2) 1.2062(2) -0.27405(16) 0.0654(7) Uani 1 1 d . . .
H15 H 0.2108 1.2512 -0.2754 0.078 Uiso 1 1 calc R . .
C16 C 0.0425(2) 1.20769(19) -0.20786(14) 0.0539(6) Uani 1 1 d . . .
H16 H 0.0704 1.2528 -0.1646 0.065 Uiso 1 1 calc R . .
C17 C -0.3896(2) 1.26758(16) -0.18743(11) 0.0419(5) Uani 1 1 d . . .
H17 H -0.3570 1.2510 -0.2412 0.050 Uiso 1 1 calc R . .
C18 C -0.26031(19) 1.27407(16) -0.13313(11) 0.0360(4) Uani 1 1 d . . .
H18 H -0.1954 1.3344 -0.1545 0.043 Uiso 1 1 calc R . .
C19 C -0.3066(2) 1.31565(18) -0.05195(13) 0.0438(5) Uani 1 1 d . . .
C20 C -0.3935(2) 1.42690(18) -0.05071(14) 0.0543(6) Uani 1 1 d . . .
H20A H -0.3344 1.4933 -0.0672 0.065 Uiso 1 1 calc R . .
H20B H -0.4260 1.4422 0.0026 0.065 Uiso 1 1 calc R . .
C21 C -0.5224(2) 1.41680(19) -0.10515(14) 0.0548(6) Uani 1 1 d . . .
H21A H -0.5885 1.3582 -0.0843 0.066 Uiso 1 1 calc R . .
H21B H -0.5717 1.4926 -0.1072 0.066 Uiso 1 1 calc R . .
C22 C -0.4776(2) 1.38089(18) -0.18763(13) 0.0523(6) Uani 1 1 d . . .
H22A H -0.5623 1.3693 -0.2197 0.063 Uiso 1 1 calc R . .
H22B H -0.4218 1.4445 -0.2110 0.063 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 C13 1.736(2) . ?
O1 C7 1.342(2) . ?
O1 C17 1.452(2) . ?
O2 C19 1.201(2) . ?
O3 C9 1.200(2) . ?
O4 C6 1.377(2) . ?
O4 C9 1.381(2) . ?
C1 C6 1.385(3) . ?
C1 C2 1.396(3) . ?
C1 C7 1.442(2) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C7 C8 1.353(3) . ?
C8 C9 1.440(3) . ?
C8 C10 1.502(3) . ?
C10 C11 1.525(3) . ?
C10 C18 1.529(2) . ?
C10 H10 0.9800 . ?
C11 C12 1.377(3) . ?
C11 C16 1.383(3) . ?
C12 C13 1.382(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(3) . ?
C14 C15 1.368(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.517(3) . ?
C17 C18 1.522(3) . ?
C17 H17 0.9800 . ?
C18 C19 1.519(3) . ?
C18 H18 0.9800 . ?
C19 C20 1.492(3) . ?
C20 C21 1.522(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.517(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?

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
C7 O1 C17 118.22(14) . . ?
C6 O4 C9 121.77(15) . . ?
C6 C1 C2 118.28(19) . . ?
C6 C1 C7 117.48(17) . . ?
C2 C1 C7 124.2(2) . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
O4 C6 C5 116.84(19) . . ?
O4 C6 C1 121.25(17) . . ?
C5 C6 C1 121.91(19) . . ?
O1 C7 C8 123.81(16) . . ?
O1 C7 C1 114.85(16) . . ?
C8 C7 C1 121.32(17) . . ?
C7 C8 C9 120.00(16) . . ?
C7 C8 C10 122.53(16) . . ?
C9 C8 C10 117.33(16) . . ?
O3 C9 O4 116.42(17) . . ?
O3 C9 C8 125.55(17) . . ?
O4 C9 C8 118.02(16) . . ?
C8 C10 C11 114.74(15) . . ?
C8 C10 C18 108.27(14) . . ?
C11 C10 C18 111.20(15) . . ?
C8 C10 H10 107.4 . . ?
C11 C10 H10 107.4 . . ?
C18 C10 H10 107.4 . . ?
C12 C11 C16 117.93(19) . . ?
C12 C11 C10 123.02(17) . . ?
C16 C11 C10 119.01(18) . . ?
C11 C12 C13 120.25(18) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 121.38(19) . . ?
C14 C13 Cl1 119.41(17) . . ?
C12 C13 Cl1 119.21(16) . . ?
C15 C14 C13 118.5(2) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C16 120.5(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 121.3(2) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
O1 C17 C22 106.30(16) . . ?
O1 C17 C18 110.25(14) . . ?
C22 C17 C18 113.02(16) . . ?
O1 C17 H17 109.1 . . ?
C22 C17 H17 109.1 . . ?
C18 C17 H17 109.1 . . ?
C19 C18 C17 109.80(15) . . ?
C19 C18 C10 113.45(16) . . ?
C17 C18 C10 111.01(15) . . ?
C19 C18 H18 107.4 . . ?
C17 C18 H18 107.4 . . ?
C10 C18 H18 107.4 . . ?
O2 C19 C20 122.6(2) . . ?
O2 C19 C18 122.15(18) . . ?
C20 C19 C18 115.22(18) . . ?
C19 C20 C21 111.04(17) . . ?
C19 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C22 C21 C20 111.26(18) . . ?
C22 C21 H21A 109.4 . . ?
C20 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C20 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C17 C22 C21 111.80(17) . . ?
C17 C22 H22A 109.3 . . ?
C21 C22 H22A 109.3 . . ?
C17 C22 H22B 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.1(3) . . . . ?
C7 C1 C2 C3 178.87(18) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C9 O4 C6 C5 -176.31(17) . . . . ?
C9 O4 C6 C1 3.1(3) . . . . ?
C4 C5 C6 O4 -179.1(2) . . . . ?
C4 C5 C6 C1 1.6(3) . . . . ?
C2 C1 C6 O4 179.39(18) . . . . ?
C7 C1 C6 O4 0.3(3) . . . . ?
C2 C1 C6 C5 -1.3(3) . . . . ?
C7 C1 C6 C5 179.67(18) . . . . ?
C17 O1 C7 C8 7.6(3) . . . . ?
C17 O1 C7 C1 -174.07(15) . . . . ?
C6 C1 C7 O1 179.67(16) . . . . ?
C2 C1 C7 O1 0.7(3) . . . . ?
C6 C1 C7 C8 -2.0(3) . . . . ?
C2 C1 C7 C8 179.01(18) . . . . ?
O1 C7 C8 C9 178.53(16) . . . . ?
C1 C7 C8 C9 0.3(3) . . . . ?
O1 C7 C8 C10 2.8(3) . . . . ?
C1 C7 C8 C10 -175.36(16) . . . . ?
C6 O4 C9 O3 175.19(19) . . . . ?
C6 O4 C9 C8 -4.7(3) . . . . ?
C7 C8 C9 O3 -176.9(2) . . . . ?
C10 C8 C9 O3 -1.0(3) . . . . ?
C7 C8 C9 O4 2.9(3) . . . . ?
C10 C8 C9 O4 178.85(16) . . . . ?
C7 C8 C10 C11 -106.8(2) . . . . ?
C9 C8 C10 C11 77.4(2) . . . . ?
C7 C8 C10 C18 18.1(2) . . . . ?
C9 C8 C10 C18 -157.75(16) . . . . ?
C8 C10 C11 C12 20.6(3) . . . . ?
C18 C10 C11 C12 -102.69(19) . . . . ?
C8 C10 C11 C16 -161.57(17) . . . . ?
C18 C10 C11 C16 75.1(2) . . . . ?
C16 C11 C12 C13 -1.7(3) . . . . ?
C10 C11 C12 C13 176.11(16) . . . . ?
C11 C12 C13 C14 -0.9(3) . . . . ?
C11 C12 C13 Cl1 179.72(15) . . . . ?
C12 C13 C14 C15 2.6(3) . . . . ?
Cl1 C13 C14 C15 -178.04(18) . . . . ?
C13 C14 C15 C16 -1.6(4) . . . . ?
C14 C15 C16 C11 -1.1(4) . . . . ?
C12 C11 C16 C15 2.7(3) . . . . ?
C10 C11 C16 C15 -175.2(2) . . . . ?
C7 O1 C17 C22 -160.83(16) . . . . ?
C7 O1 C17 C18 -38.0(2) . . . . ?
O1 C17 C18 C19 -67.69(19) . . . . ?
C22 C17 C18 C19 51.1(2) . . . . ?
O1 C17 C18 C10 58.57(19) . . . . ?
C22 C17 C18 C10 177.37(16) . . . . ?
C8 C10 C18 C19 76.92(19) . . . . ?
C11 C10 C18 C19 -156.15(16) . . . . ?
C8 C10 C18 C17 -47.28(19) . . . . ?
C11 C10 C18 C17 79.65(18) . . . . ?
C17 C18 C19 O2 127.0(2) . . . . ?
C10 C18 C19 O2 2.1(3) . . . . ?
C17 C18 C19 C20 -51.7(2) . . . . ?
C10 C18 C19 C20 -176.56(15) . . . . ?
O2 C19 C20 C21 -125.2(2) . . . . ?
C18 C19 C20 C21 53.5(2) . . . . ?
C19 C20 C21 C22 -53.5(2) . . . . ?
O1 C17 C22 C21 66.8(2) . . . . ?
C18 C17 C22 C21 -54.3(2) . . . . ?
C20 C21 C22 C17 54.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.027
####################################################################### 
# 
# 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_ja
_database_code_depnum_ccdc_archive 'CCDC 1508098'
_audit_update_record             
;
2016-10-04 deposited with the CCDC.
2017-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C88 H68 Cl4 O16'
_chemical_formula_weight         1523.22

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   9.3379(2)
_cell_length_b                   11.2530(3)
_cell_length_c                   17.0022(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1786.58(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3239
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      25.34

_exptl_crystal_description       BAR
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7728
_diffrn_reflns_av_R_equivalents  0.0130
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.34
_reflns_number_total             3239
_reflns_number_gt                2984
_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)+(0.0418P)²+0.2572P] 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(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3239
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0730
_refine_ls_wR_factor_gt          0.0701
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_refine_ls_shift/su_max          0.001
_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 0.07831(6) 0.98160(5) 0.08708(3) 0.06420(16) Uani 1 1 d . . .
O1 O 0.33140(13) 0.85578(10) 0.42139(7) 0.0460(3) Uani 1 1 d . . .
O2 O 0.11204(13) 0.92547(11) 0.42701(8) 0.0549(3) Uani 1 1 d . . .
C9 C 0.23426(18) 0.94667(14) 0.40981(10) 0.0394(4) Uani 1 1 d . . .
C1 C 0.52926(17) 0.97882(16) 0.38130(9) 0.0376(4) Uani 1 1 d . . .
C6 C 0.47549(19) 0.87191(15) 0.40933(10) 0.0408(4) Uani 1 1 d . . .
C16 C 0.17907(17) 1.15593(14) 0.36804(9) 0.0358(3) Uani 1 1 d . . .
H16 H 0.1168 1.1563 0.4144 0.043 Uiso 1 1 calc R . .
O3 O 0.48577(12) 1.17353(10) 0.33770(7) 0.0444(3) Uani 1 1 d . . .
C10 C 0.11894(18) 1.07308(15) 0.23202(10) 0.0400(4) Uani 1 1 d . . .
H10 H 0.2016 1.0270 0.2334 0.048 Uiso 1 1 calc R . .
C7 C 0.42794(17) 1.07263(14) 0.36498(8) 0.0343(3) Uani 1 1 d . . .
C15 C 0.08329(18) 1.14340(14) 0.29562(9) 0.0369(3) Uani 1 1 d . . .
C17 C 0.26024(17) 1.27394(14) 0.36671(9) 0.0371(4) Uani 1 1 d . . .
H17 H 0.1953 1.3342 0.3454 0.045 Uiso 1 1 calc R . .
C8 C 0.28619(17) 1.05748(14) 0.37864(9) 0.0338(3) Uani 1 1 d . . .
C2 C 0.67662(18) 0.98881(19) 0.36980(11) 0.0509(4) Uani 1 1 d . . .
H2 H 0.7156 1.0596 0.3513 0.061 Uiso 1 1 calc R . .
C3 C 0.7646(2) 0.8931(2) 0.38603(13) 0.0630(6) Uani 1 1 d . . .
H3 H 0.8627 0.8992 0.3773 0.076 Uiso 1 1 calc R . .
C11 C 0.0316(2) 1.07110(16) 0.16624(10) 0.0449(4) Uani 1 1 d . . .
C18 C 0.3900(2) 1.26772(15) 0.31249(9) 0.0423(4) Uani 1 1 d . . .
H18 H 0.3576 1.2512 0.2588 0.051 Uiso 1 1 calc R . .
C5 C 0.5640(2) 0.77738(18) 0.42711(11) 0.0560(5) Uani 1 1 d . . .
H5 H 0.5265 0.7070 0.4470 0.067 Uiso 1 1 calc R . .
C22 C 0.30689(19) 1.31566(16) 0.44822(10) 0.0436(4) Uani 1 1 d . . .
O4 O 0.27770(18) 1.26127(14) 0.50680(8) 0.0688(4) Uani 1 1 d . . .
C20 C 0.5226(2) 1.41668(18) 0.39489(12) 0.0552(5) Uani 1 1 d . . .
H20A H 0.5721 1.4924 0.3928 0.066 Uiso 1 1 calc R . .
H20B H 0.5886 1.3580 0.4158 0.066 Uiso 1 1 calc R . .
C19 C 0.4778(2) 1.38063(17) 0.31242(11) 0.0517(5) Uani 1 1 d . . .
H19A H 0.4222 1.4442 0.2890 0.062 Uiso 1 1 calc R . .
H19B H 0.5627 1.3689 0.2804 0.062 Uiso 1 1 calc R . .
C21 C 0.3940(2) 1.42710(17) 0.44929(12) 0.0547(5) Uani 1 1 d . . .
H21A H 0.4266 1.4426 0.5025 0.066 Uiso 1 1 calc R . .
H21B H 0.3349 1.4935 0.4328 0.066 Uiso 1 1 calc R . .
C12 C -0.0902(2) 1.13919(18) 0.16198(12) 0.0575(5) Uani 1 1 d . . .
H12 H -0.1462 1.1396 0.1167 0.069 Uiso 1 1 calc R . .
C4 C 0.7089(2) 0.7893(2) 0.41478(13) 0.0657(6) Uani 1 1 d . . .
H4 H 0.7697 0.7262 0.4261 0.079 Uiso 1 1 calc R . .
C14 C -0.0430(2) 1.20774(18) 0.29253(12) 0.0542(5) Uani 1 1 d . . .
H14 H -0.0714 1.2524 0.3359 0.065 Uiso 1 1 calc R . .
C13 C -0.1272(2) 1.2063(2) 0.22584(14) 0.0657(6) Uani 1 1 d . . .
H13 H -0.2103 1.2517 0.2243 0.079 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 C11 1.7367(19) . ?
O1 C6 1.373(2) . ?
O1 C9 1.381(2) . ?
O2 C9 1.202(2) . ?
C9 C8 1.439(2) . ?
C1 C6 1.388(2) . ?
C1 C2 1.394(2) . ?
C1 C7 1.445(2) . ?
C6 C5 1.381(2) . ?
C16 C8 1.503(2) . ?
C16 C15 1.528(2) . ?
C16 C17 1.529(2) . ?
C16 H16 0.9800 . ?
O3 C7 1.3402(19) . ?
O3 C18 1.451(2) . ?
C10 C15 1.381(2) . ?
C10 C11 1.384(2) . ?
C10 H10 0.9300 . ?
C7 C8 1.355(2) . ?
C15 C14 1.385(2) . ?
C17 C18 1.524(2) . ?
C17 C22 1.527(2) . ?
C17 H17 0.9800 . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(3) . ?
C3 H3 0.9300 . ?
C11 C12 1.373(3) . ?
C18 C19 1.512(2) . ?
C18 H18 0.9800 . ?
C5 C4 1.376(3) . ?
C5 H5 0.9300 . ?
C22 O4 1.200(2) . ?
C22 C21 1.495(3) . ?
C20 C19 1.518(3) . ?
C20 C21 1.521(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C12 C13 1.367(3) . ?
C12 H12 0.9300 . ?
C4 H4 0.9300 . ?
C14 C13 1.380(3) . ?
C14 H14 0.9300 . ?
C13 H13 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 O1 C9 121.63(13) . . ?
O2 C9 O1 116.23(14) . . ?
O2 C9 C8 125.55(15) . . ?
O1 C9 C8 118.22(14) . . ?
C6 C1 C2 118.36(16) . . ?
C6 C1 C7 117.54(15) . . ?
C2 C1 C7 124.09(17) . . ?
O1 C6 C5 116.89(17) . . ?
O1 C6 C1 121.35(15) . . ?
C5 C6 C1 121.76(17) . . ?
C8 C16 C15 114.70(13) . . ?
C8 C16 C17 108.18(13) . . ?
C15 C16 C17 110.99(13) . . ?
C8 C16 H16 107.6 . . ?
C15 C16 H16 107.6 . . ?
C17 C16 H16 107.6 . . ?
C7 O3 C18 118.20(13) . . ?
C15 C10 C11 120.00(16) . . ?
C15 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
O3 C7 C8 124.04(14) . . ?
O3 C7 C1 114.94(14) . . ?
C8 C7 C1 121.00(15) . . ?
C10 C15 C14 118.37(16) . . ?
C10 C15 C16 122.87(15) . . ?
C14 C15 C16 118.73(15) . . ?
C18 C17 C22 109.65(14) . . ?
C18 C17 C16 111.29(13) . . ?
C22 C17 C16 113.27(14) . . ?
C18 C17 H17 107.5 . . ?
C22 C17 H17 107.5 . . ?
C16 C17 H17 107.5 . . ?
C7 C8 C9 120.09(14) . . ?
C7 C8 C16 122.47(14) . . ?
C9 C8 C16 117.29(14) . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.68(19) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C12 C11 C10 121.44(17) . . ?
C12 C11 Cl1 119.38(14) . . ?
C10 C11 Cl1 119.18(14) . . ?
O3 C18 C19 106.24(14) . . ?
O3 C18 C17 110.17(12) . . ?
C19 C18 C17 113.14(14) . . ?
O3 C18 H18 109.1 . . ?
C19 C18 H18 109.1 . . ?
C17 C18 H18 109.1 . . ?
C4 C5 C6 118.7(2) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
O4 C22 C21 122.77(17) . . ?
O4 C22 C17 122.11(16) . . ?
C21 C22 C17 115.11(15) . . ?
C19 C20 C21 111.39(16) . . ?
C19 C20 H20A 109.3 . . ?
C21 C20 H20A 109.3 . . ?
C19 C20 H20B 109.3 . . ?
C21 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
C18 C19 C20 111.91(15) . . ?
C18 C19 H19A 109.2 . . ?
C20 C19 H19A 109.2 . . ?
C18 C19 H19B 109.2 . . ?
C20 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C22 C21 C20 110.95(15) . . ?
C22 C21 H21A 109.4 . . ?
C20 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C20 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C13 C12 C11 118.39(18) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C3 C4 C5 120.78(19) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C13 C14 C15 120.69(19) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C12 C13 C14 121.02(19) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?

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
C6 O1 C9 O2 -175.23(16) . . . . ?
C6 O1 C9 C8 4.8(2) . . . . ?
C9 O1 C6 C5 176.25(15) . . . . ?
C9 O1 C6 C1 -3.1(2) . . . . ?
C2 C1 C6 O1 -179.49(15) . . . . ?
C7 C1 C6 O1 -0.2(2) . . . . ?
C2 C1 C6 C5 1.2(2) . . . . ?
C7 C1 C6 C5 -179.55(15) . . . . ?
C18 O3 C7 C8 -7.5(2) . . . . ?
C18 O3 C7 C1 173.94(13) . . . . ?
C6 C1 C7 O3 -179.67(14) . . . . ?
C2 C1 C7 O3 -0.4(2) . . . . ?
C6 C1 C7 C8 1.8(2) . . . . ?
C2 C1 C7 C8 -179.01(15) . . . . ?
C11 C10 C15 C14 2.1(2) . . . . ?
C11 C10 C15 C16 -176.14(15) . . . . ?
C8 C16 C15 C10 -20.3(2) . . . . ?
C17 C16 C15 C10 102.69(17) . . . . ?
C8 C16 C15 C14 161.50(15) . . . . ?
C17 C16 C15 C14 -75.52(19) . . . . ?
C8 C16 C17 C18 47.01(16) . . . . ?
C15 C16 C17 C18 -79.65(16) . . . . ?
C8 C16 C17 C22 -77.07(17) . . . . ?
C15 C16 C17 C22 156.27(14) . . . . ?
O3 C7 C8 C9 -178.51(14) . . . . ?
C1 C7 C8 C9 -0.1(2) . . . . ?
O3 C7 C8 C16 -3.1(2) . . . . ?
C1 C7 C8 C16 175.37(13) . . . . ?
O2 C9 C8 C7 176.84(17) . . . . ?
O1 C9 C8 C7 -3.1(2) . . . . ?
O2 C9 C8 C16 1.2(3) . . . . ?
O1 C9 C8 C16 -178.81(14) . . . . ?
C15 C16 C8 C7 106.75(17) . . . . ?
C17 C16 C8 C7 -17.7(2) . . . . ?
C15 C16 C8 C9 -77.69(18) . . . . ?
C17 C16 C8 C9 157.83(14) . . . . ?
C6 C1 C2 C3 0.3(2) . . . . ?
C7 C1 C2 C3 -178.96(16) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C15 C10 C11 C12 0.9(3) . . . . ?
C15 C10 C11 Cl1 -179.80(13) . . . . ?
C7 O3 C18 C19 160.68(14) . . . . ?
C7 O3 C18 C17 37.79(18) . . . . ?
C22 C17 C18 O3 67.71(16) . . . . ?
C16 C17 C18 O3 -58.40(17) . . . . ?
C22 C17 C18 C19 -51.03(18) . . . . ?
C16 C17 C18 C19 -177.14(14) . . . . ?
O1 C6 C5 C4 179.08(17) . . . . ?
C1 C6 C5 C4 -1.6(3) . . . . ?
C18 C17 C22 O4 -127.01(19) . . . . ?
C16 C17 C22 O4 -2.0(2) . . . . ?
C18 C17 C22 C21 51.64(19) . . . . ?
C16 C17 C22 C21 176.61(14) . . . . ?
O3 C18 C19 C20 -66.75(19) . . . . ?
C17 C18 C19 C20 54.2(2) . . . . ?
C21 C20 C19 C18 -54.6(2) . . . . ?
O4 C22 C21 C20 125.1(2) . . . . ?
C17 C22 C21 C20 -53.6(2) . . . . ?
C19 C20 C21 C22 53.6(2) . . . . ?
C10 C11 C12 C13 -2.5(3) . . . . ?
Cl1 C11 C12 C13 178.12(16) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C6 C5 C4 C3 0.5(3) . . . . ?
C10 C15 C14 C13 -3.3(3) . . . . ?
C16 C15 C14 C13 174.95(19) . . . . ?
C11 C12 C13 C14 1.3(3) . . . . ?
C15 C14 C13 C12 1.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.027
