# 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. 
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#######################################################################

data_cu_16er005_0m
_database_code_depnum_ccdc_archive 'CCDC 1533751'
_audit_update_record             
;
2017-02-20 deposited with the CCDC.
2017-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        (S)-21
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H32 Cl4 O6'
_chemical_formula_weight         774.48

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'
O O 0.0492 0.0322 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   8.0715(2)
_cell_length_b                   8.9946(2)
_cell_length_c                   25.1406(6)
_cell_angle_alpha                90.000(0)
_cell_angle_beta                 98.0371(8)
_cell_angle_gamma                90.000(0)
_cell_volume                     1807.28(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9253
_cell_measurement_theta_min      3.55
_cell_measurement_theta_max      74.63

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    3.384
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         microsource
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  CMOS
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            40507
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.55
_diffrn_reflns_theta_max         74.61
_reflns_number_total             7306
_reflns_number_gt                7151
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0237P)²+0.4258P] 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   0.074(6)
_refine_ls_number_reflns         7306
_refine_ls_number_parameters     493
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_ref         0.0588
_refine_ls_wR_factor_gt          0.0584
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_chemical_absolute_configuration ad

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
Cl1A Cl 1.00850(5) 0.10159(4) 0.826190(15) 0.02520(9) Uani 1 1 d . . .
Cl2B Cl -0.25077(5) 0.72598(5) 0.764441(16) 0.03035(10) Uani 1 1 d . . .
Cl1B Cl -0.11191(5) 0.20260(4) 0.678038(15) 0.02397(8) Uani 1 1 d . . .
Cl2A Cl 1.37935(5) 0.51381(6) 0.744446(17) 0.03467(11) Uani 1 1 d . . .
O2B O 0.83472(13) 0.52648(12) 0.49189(5) 0.0218(2) Uani 1 1 d . . .
O3B O 0.65599(15) 0.56489(12) 0.55076(5) 0.0236(2) Uani 1 1 d . . .
O3A O 0.31919(14) 0.61009(13) 0.95906(4) 0.0225(2) Uani 1 1 d . . .
O1A O 0.34510(13) 0.12614(11) 0.95264(4) 0.0157(2) Uani 1 1 d . . .
O1B O 0.64686(13) 0.08120(11) 0.55301(4) 0.0171(2) Uani 1 1 d . . .
O2A O 0.15167(14) 0.55826(12) 1.02029(5) 0.0234(2) Uani 1 1 d . . .
C14A C 0.74759(19) 0.43428(16) 0.89944(6) 0.0166(3) Uani 1 1 d . . .
C8A C 0.41694(18) 0.07375(16) 0.90901(6) 0.0149(3) Uani 1 1 d . . .
C2A C 0.46093(18) 0.33116(16) 0.91041(6) 0.0136(3) Uani 1 1 d . . .
C13A C 0.63089(18) 0.39225(16) 0.93854(6) 0.0159(3) Uani 1 1 d . . .
H13A H 0.6104 0.4789 0.9597 0.019 Uiso 1 1 calc R . .
H13B H 0.6840 0.3173 0.9629 0.019 Uiso 1 1 calc R . .
C12A C 0.25803(18) 0.51745(17) 0.98518(6) 0.0173(3) Uani 1 1 d . . .
C14B C 0.24932(19) 0.42532(16) 0.59780(6) 0.0163(3) Uani 1 1 d . . .
C18B C -0.17784(19) 0.4736(2) 0.71470(6) 0.0210(3) Uani 1 1 d . . .
H18B H -0.2444 0.4245 0.7364 0.025 Uiso 1 1 calc R . .
C4A C 0.54766(19) 0.15427(18) 0.83452(6) 0.0184(3) Uani 1 1 d . . .
H4A H 0.5901 0.2290 0.8147 0.022 Uiso 1 1 calc R . .
C1B C 0.63257(18) 0.23414(16) 0.55389(6) 0.0149(3) Uani 1 1 d . . .
C20A C 1.1653(2) 0.5795(2) 0.81478(6) 0.0245(4) Uani 1 1 d . . .
H20A H 1.1977 0.6780 0.8116 0.029 Uiso 1 1 calc R . .
C16A C 0.99881(18) 0.39385(18) 0.85424(6) 0.0181(3) Uani 1 1 d . . .
C10B C 0.8290(2) 0.26030(17) 0.48369(6) 0.0196(3) Uani 1 1 d . . .
H10A H 0.7644 0.2074 0.4542 0.023 Uiso 1 1 calc R . .
H10B H 0.9164 0.1955 0.5010 0.023 Uiso 1 1 calc R . .
C21A C 1.05166(19) 0.54055(19) 0.84924(6) 0.0219(3) Uani 1 1 d . . .
H21A H 1.0096 0.6143 0.8695 0.026 Uiso 1 1 calc R . .
C10A C 0.1760(2) 0.29298(18) 1.02736(6) 0.0193(3) Uani 1 1 d . . .
H10C H 0.2497 0.2492 1.0570 0.023 Uiso 1 1 calc R . .
H10D H 0.0963 0.2186 1.0120 0.023 Uiso 1 1 calc R . .
C6A C 0.48945(19) -0.10640(18) 0.84836(7) 0.0222(3) Uani 1 1 d . . .
H6A H 0.4948 -0.2045 0.8370 0.027 Uiso 1 1 calc R . .
C12B C 0.72593(19) 0.47786(16) 0.52493(6) 0.0177(3) Uani 1 1 d . . .
C2B C 0.51239(19) 0.28181(17) 0.59167(6) 0.0150(3) Uani 1 1 d . . .
C9B C 0.71930(18) 0.31503(16) 0.52298(6) 0.0155(3) Uani 1 1 d . . .
C5B C 0.3833(2) -0.0527(2) 0.67338(6) 0.0254(4) Uani 1 1 d . . .
H5B H 0.3232 -0.0804 0.7008 0.031 Uiso 1 1 calc R . .
C9A C 0.27337(18) 0.35532(17) 0.98580(6) 0.0150(3) Uani 1 1 d . . .
C18A C 1.18163(19) 0.3222(2) 0.78864(6) 0.0215(3) Uani 1 1 d . . .
H18A H 1.2250 0.2492 0.7683 0.026 Uiso 1 1 calc R . .
C16B C 0.00525(18) 0.46572(18) 0.64510(6) 0.0174(3) Uani 1 1 d . . .
C5A C 0.55051(19) 0.00630(19) 0.81836(6) 0.0227(3) Uani 1 1 d . . .
H5A H 0.5938 -0.0177 0.7871 0.027 Uiso 1 1 calc R . .
C15A C 0.88118(19) 0.35441(18) 0.89176(6) 0.0182(3) Uani 1 1 d . . .
C7B C 0.5538(2) -0.12489(17) 0.60498(6) 0.0216(3) Uani 1 1 d . . .
H7B H 0.6067 -0.1967 0.5867 0.026 Uiso 1 1 calc R . .
C17A C 1.06746(19) 0.28696(19) 0.82313(6) 0.0195(3) Uani 1 1 d . . .
C17B C -0.09499(18) 0.39574(18) 0.67866(6) 0.0178(3) Uani 1 1 d . . .
C21B C 0.0155(2) 0.62074(18) 0.64827(7) 0.0225(3) Uani 1 1 d . . .
H21B H 0.0773 0.6713 0.6254 0.027 Uiso 1 1 calc R . .
C8B C 0.55914(18) 0.02521(17) 0.59261(6) 0.0165(3) Uani 1 1 d . . .
C6B C 0.4636(2) -0.16071(18) 0.64664(7) 0.0246(3) Uani 1 1 d . . .
H6B H 0.4570 -0.2596 0.6569 0.030 Uiso 1 1 calc R . .
C15B C 0.10010(19) 0.38265(17) 0.60863(6) 0.0174(3) Uani 1 1 d . . .
C11B C 0.9024(2) 0.40397(19) 0.46425(6) 0.0230(3) Uani 1 1 d . . .
H11A H 1.0235 0.4025 0.4724 0.028 Uiso 1 1 calc R . .
H11B H 0.8721 0.4144 0.4257 0.028 Uiso 1 1 calc R . .
C13B C 0.35050(18) 0.34945(17) 0.56052(6) 0.0163(3) Uani 1 1 d . . .
H13C H 0.3798 0.4204 0.5343 0.020 Uiso 1 1 calc R . .
H13D H 0.2844 0.2712 0.5413 0.020 Uiso 1 1 calc R . .
C1A C 0.35389(18) 0.27959(16) 0.95175(6) 0.0136(3) Uani 1 1 d . . .
C3A C 0.47983(18) 0.18747(16) 0.88100(5) 0.0141(3) Uani 1 1 d . . .
C19B C -0.15860(19) 0.62579(19) 0.71735(6) 0.0224(3) Uani 1 1 d . . .
C7A C 0.4204(2) -0.07561(17) 0.89506(6) 0.0196(3) Uani 1 1 d . . .
H7A H 0.3796 -0.1499 0.9154 0.024 Uiso 1 1 calc R . .
C19A C 1.22894(19) 0.4695(2) 0.78543(6) 0.0246(4) Uani 1 1 d . . .
C4B C 0.3923(2) 0.0978(2) 0.65935(6) 0.0214(3) Uani 1 1 d . . .
H4B H 0.3392 0.1703 0.6773 0.026 Uiso 1 1 calc R . .
C3B C 0.48194(19) 0.13614(17) 0.61816(6) 0.0165(3) Uani 1 1 d . . .
C20B C -0.0635(2) 0.7009(2) 0.68434(7) 0.0247(3) Uani 1 1 d . . .
H20B H -0.0529 0.8038 0.6864 0.030 Uiso 1 1 calc R . .
C11A C 0.0877(3) 0.4292(2) 1.04527(8) 0.0362(5) Uani 1 1 d . . .
H11C H -0.0321 0.4207 1.0345 0.043 Uiso 1 1 calc R . .
H11D H 0.1089 0.4385 1.0841 0.043 Uiso 1 1 calc R . .
H2A H 0.401(2) 0.410(2) 0.8892(7) 0.012(4) Uiso 1 1 d . . .
H2B H 0.564(2) 0.350(2) 0.6166(7) 0.015(4) Uiso 1 1 d . . .
H15A H 0.903(2) 0.263(2) 0.9119(7) 0.021(5) Uiso 1 1 d . . .
H14B H 0.304(2) 0.514(2) 0.6154(7) 0.018(4) Uiso 1 1 d . . .
H14A H 0.719(2) 0.528(2) 0.8779(7) 0.025(5) Uiso 1 1 d . . .
H15B H 0.048(2) 0.289(2) 0.5937(7) 0.018(4) Uiso 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
Cl1A C17A 1.739(2) . ?
Cl2B C19B 1.7360(17) . ?
Cl1B C17B 1.7426(19) . ?
Cl2A C19A 1.7448(17) . ?
O2B C12B 1.362(2) . ?
O2B C11B 1.450(2) . ?
O3B C12B 1.2066(19) . ?
O3A C12A 1.208(2) . ?
O1A C1A 1.3824(18) . ?
O1A C8A 1.3925(18) . ?
O1B C1B 1.3810(19) . ?
O1B C8B 1.3940(18) . ?
O2A C12A 1.3648(19) . ?
O2A C11A 1.449(2) . ?
C14A C15A 1.332(2) . ?
C14A C13A 1.502(2) . ?
C8A C3A 1.378(2) . ?
C8A C7A 1.390(2) . ?
C2A C3A 1.507(2) . ?
C2A C1A 1.514(2) . ?
C2A C13A 1.553(2) . ?
C12A C9A 1.464(2) . ?
C14B C15B 1.328(2) . ?
C14B C13B 1.492(2) . ?
C18B C19B 1.378(3) . ?
C18B C17B 1.389(2) . ?
C4A C3A 1.390(2) . ?
C4A C5A 1.393(2) . ?
C1B C9B 1.332(2) . ?
C1B C2B 1.512(2) . ?
C20A C19A 1.376(3) . ?
C20A C21A 1.392(2) . ?
C16A C21A 1.398(2) . ?
C16A C17A 1.402(2) . ?
C16A C15A 1.472(2) . ?
C10B C9B 1.499(2) . ?
C10B C11B 1.530(2) . ?
C10A C9A 1.501(2) . ?
C10A C11A 1.517(2) . ?
C6A C5A 1.394(3) . ?
C6A C7A 1.396(2) . ?
C12B C9B 1.466(2) . ?
C2B C3B 1.506(2) . ?
C2B C13B 1.551(2) . ?
C5B C6B 1.392(3) . ?
C5B C4B 1.403(3) . ?
C9A C1A 1.332(2) . ?
C18A C19A 1.384(3) . ?
C18A C17A 1.387(2) . ?
C16B C17B 1.398(2) . ?
C16B C21B 1.398(2) . ?
C16B C15B 1.477(2) . ?
C7B C8B 1.387(2) . ?
C7B C6B 1.394(2) . ?
C21B C20B 1.382(2) . ?
C8B C3B 1.382(2) . ?
C19B C20B 1.383(2) . ?
C4B C3B 1.387(2) . ?

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
C12B O2B C11B 111.50(12) . . ?
C1A O1A C8A 107.30(11) . . ?
C1B O1B C8B 107.26(11) . . ?
C12A O2A C11A 111.06(12) . . ?
C15A C14A C13A 123.62(14) . . ?
C3A C8A C7A 124.51(14) . . ?
C3A C8A O1A 112.01(12) . . ?
C7A C8A O1A 123.46(13) . . ?
C3A C2A C1A 100.40(12) . . ?
C3A C2A C13A 112.53(12) . . ?
C1A C2A C13A 110.37(12) . . ?
C14A C13A C2A 112.69(12) . . ?
O3A C12A O2A 120.51(14) . . ?
O3A C12A C9A 130.74(15) . . ?
O2A C12A C9A 108.73(13) . . ?
C15B C14B C13B 126.04(14) . . ?
C19B C18B C17B 118.11(15) . . ?
C3A C4A C5A 118.35(14) . . ?
C9B C1B O1B 118.87(13) . . ?
C9B C1B C2B 130.33(14) . . ?
O1B C1B C2B 110.79(13) . . ?
C19A C20A C21A 118.72(16) . . ?
C21A C16A C17A 116.61(14) . . ?
C21A C16A C15A 121.16(14) . . ?
C17A C16A C15A 122.21(15) . . ?
C9B C10B C11B 102.94(13) . . ?
C20A C21A C16A 121.98(16) . . ?
C9A C10A C11A 102.60(13) . . ?
C5A C6A C7A 121.57(15) . . ?
O3B C12B O2B 120.65(14) . . ?
O3B C12B C9B 130.42(15) . . ?
O2B C12B C9B 108.90(13) . . ?
C3B C2B C1B 100.95(12) . . ?
C3B C2B C13B 112.76(13) . . ?
C1B C2B C13B 111.30(12) . . ?
C1B C9B C12B 123.07(14) . . ?
C1B C9B C10B 127.73(14) . . ?
C12B C9B C10B 109.14(13) . . ?
C6B C5B C4B 120.54(15) . . ?
C1A C9A C12A 123.43(14) . . ?
C1A C9A C10A 127.31(14) . . ?
C12A C9A C10A 109.14(13) . . ?
C19A C18A C17A 117.90(16) . . ?
C17B C16B C21B 116.71(14) . . ?
C17B C16B C15B 122.75(15) . . ?
C21B C16B C15B 120.53(14) . . ?
C4A C5A C6A 121.04(15) . . ?
C14A C15A C16A 124.79(15) . . ?
C8B C7B C6B 115.42(15) . . ?
C18A C17A C16A 122.75(16) . . ?
C18A C17A Cl1A 117.17(13) . . ?
C16A C17A Cl1A 120.08(12) . . ?
C18B C17B C16B 122.61(15) . . ?
C18B C17B Cl1B 117.67(12) . . ?
C16B C17B Cl1B 119.66(12) . . ?
C20B C21B C16B 121.90(16) . . ?
C3B C8B C7B 124.64(15) . . ?
C3B C8B O1B 112.23(14) . . ?
C7B C8B O1B 123.13(14) . . ?
C5B C6B C7B 121.91(15) . . ?
C14B C15B C16B 123.00(14) . . ?
O2B C11B C10B 107.47(13) . . ?
C14B C13B C2B 111.02(12) . . ?
C9A C1A O1A 118.00(13) . . ?
C9A C1A C2A 131.36(14) . . ?
O1A C1A C2A 110.63(12) . . ?
C8A C3A C4A 119.10(14) . . ?
C8A C3A C2A 108.43(12) . . ?
C4A C3A C2A 132.46(14) . . ?
C18B C19B C20B 121.65(15) . . ?
C18B C19B Cl2B 119.50(13) . . ?
C20B C19B Cl2B 118.83(14) . . ?
C8A C7A C6A 115.39(15) . . ?
C20A C19A C18A 122.04(15) . . ?
C20A C19A Cl2A 119.65(14) . . ?
C18A C19A Cl2A 118.27(14) . . ?
C3B C4B C5B 118.56(15) . . ?
C8B C3B C4B 118.94(15) . . ?
C8B C3B C2B 108.11(13) . . ?
C4B C3B C2B 132.92(14) . . ?
C19B C20B C21B 118.97(17) . . ?
O2A C11A C10A 107.94(14) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        74.61
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_cu_16er004ter_0m
_database_code_depnum_ccdc_archive 'CCDC 1533736'
_audit_update_record             
;
2017-02-20 deposited with the CCDC.
2017-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        (R,R)-19
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H34 Br2 O6'
_chemical_formula_weight         818.53

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   9.629(5)
_cell_length_b                   17.514(5)
_cell_length_c                   10.738(5)
_cell_angle_alpha                90.000(0)
_cell_angle_beta                 98.230(5)
_cell_angle_gamma                90.000(0)
_cell_volume                     1792.2(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9866
_cell_measurement_theta_min      4.64
_cell_measurement_theta_max      74.57

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    3.281
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         microsource
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  CMOS
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33822
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.16
_diffrn_reflns_theta_max         74.56
_reflns_number_total             7204
_reflns_number_gt                6989
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0000P)²+0.9798P] 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   0.047(9)
_refine_ls_number_reflns         7204
_refine_ls_number_parameters     469
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0544
_refine_ls_wR_factor_gt          0.0537
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_chemical_absolute_configuration ad

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
Br1' Br 0.00371(3) -0.202314(14) 0.65541(2) 0.02874(7) Uani 1 1 d . . .
Br1 Br 0.59100(3) 0.262324(13) 1.15382(2) 0.02514(6) Uani 1 1 d . . .
O1 O 0.50768(16) 0.46716(9) 0.34922(14) 0.0146(3) Uani 1 1 d . . .
O3' O -0.12862(17) 0.18001(11) 0.58854(16) 0.0252(4) Uani 1 1 d . . .
O3 O 0.36205(18) 0.35850(10) 0.52899(16) 0.0253(4) Uani 1 1 d . . .
O1' O 0.07852(15) 0.32479(9) 0.66792(14) 0.0156(3) Uani 1 1 d . . .
O2 O 0.58156(18) 0.31535(9) 0.56453(16) 0.0245(4) Uani 1 1 d . . .
C17 C 0.5385(2) 0.42798(12) 0.8077(2) 0.0137(4) Uani 1 1 d . . .
O2' O 0.06618(19) 0.14961(11) 0.51324(16) 0.0270(4) Uani 1 1 d . . .
C11' C 0.0654(2) 0.39508(13) 0.7200(2) 0.0158(4) Uani 1 1 d . . .
C10' C 0.0716(2) 0.46460(14) 0.6596(2) 0.0208(5) Uani 1 1 d . . .
H10' H 0.0817 0.4677 0.5749 0.025 Uiso 1 1 calc R . .
C18 C 0.6691(2) 0.41713(13) 0.8803(2) 0.0149(4) Uani 1 1 d . . .
H18 H 0.7460 0.4446 0.8612 0.018 Uiso 1 1 calc R . .
C21 C 0.4412(2) 0.33480(14) 0.9391(2) 0.0207(5) Uani 1 1 d . . .
H21 H 0.3649 0.3069 0.9583 0.025 Uiso 1 1 calc R . .
C22 C 0.4257(2) 0.38522(14) 0.8382(2) 0.0179(5) Uani 1 1 d . . .
H22 H 0.3381 0.3906 0.7897 0.021 Uiso 1 1 calc R . .
C2 C 0.5878(2) 0.55952(13) 0.7297(2) 0.0149(4) Uani 1 1 d . . .
H2 H 0.6624 0.5611 0.7950 0.018 Uiso 1 1 calc R . .
C20 C 0.5713(2) 0.32677(13) 1.0101(2) 0.0175(4) Uani 1 1 d . . .
C4 C 0.4366(3) 0.62968(13) 0.5582(2) 0.0179(4) Uani 1 1 d . . .
H4A H 0.4360 0.6810 0.5241 0.021 Uiso 1 1 calc R . .
H4B H 0.3467 0.6211 0.5867 0.021 Uiso 1 1 calc R . .
C7 C 0.3756(2) 0.65092(13) 0.2476(2) 0.0161(4) Uani 1 1 d . . .
H7 H 0.3539 0.6965 0.2849 0.019 Uiso 1 1 calc R . .
C13' C 0.0970(2) 0.19176(13) 0.7248(2) 0.0135(4) Uani 1 1 d . . .
C17' C 0.0516(2) 0.05280(13) 0.7853(2) 0.0161(4) Uani 1 1 d . . .
C12' C 0.0738(2) 0.27207(13) 0.76367(18) 0.0146(4) Uani 1 1 d . . .
C21' C -0.0969(3) -0.05408(14) 0.7077(2) 0.0200(5) Uani 1 1 d . . .
H21' H -0.1859 -0.0744 0.6832 0.024 Uiso 1 1 calc R . .
C5 C 0.4538(2) 0.57298(13) 0.4550(2) 0.0125(4) Uani 1 1 d . . .
C22' C -0.0802(2) 0.02144(13) 0.7479(2) 0.0174(4) Uani 1 1 d . . .
H22' H -0.1594 0.0516 0.7496 0.021 Uiso 1 1 calc R . .
C20' C 0.0229(3) -0.09856(14) 0.7051(2) 0.0215(5) Uani 1 1 d . . .
C14' C 0.2434(2) 0.18161(14) 0.6833(2) 0.0197(5) Uani 1 1 d . . .
H14C H 0.2897 0.2305 0.6791 0.024 Uiso 1 1 calc R . .
H14D H 0.3023 0.1488 0.7415 0.024 Uiso 1 1 calc R . .
C16 C 0.4851(2) 0.37107(13) 0.5521(2) 0.0176(4) Uani 1 1 d . . .
C8 C 0.3589(2) 0.64337(14) 0.1177(2) 0.0183(5) Uani 1 1 d . . .
H8 H 0.3247 0.6844 0.0674 0.022 Uiso 1 1 calc R . .
C12 C 0.5023(2) 0.50070(12) 0.46592(19) 0.0125(4) Uani 1 1 d . . .
C6 C 0.4261(2) 0.58822(12) 0.3209(2) 0.0122(4) Uani 1 1 d . . .
C6' C 0.0515(2) 0.38731(14) 0.8474(2) 0.0165(5) Uani 1 1 d . . .
C11 C 0.4590(2) 0.52154(12) 0.2615(2) 0.0131(4) Uani 1 1 d . . .
C9 C 0.3927(2) 0.57493(15) 0.0609(2) 0.0213(5) Uani 1 1 d . . .
H9 H 0.3806 0.5716 -0.0264 0.026 Uiso 1 1 calc R . .
C18' C 0.1697(2) 0.00683(14) 0.7811(2) 0.0222(5) Uani 1 1 d . . .
H18' H 0.2589 0.0268 0.8059 0.027 Uiso 1 1 calc R . .
C10 C 0.4435(2) 0.51248(13) 0.1317(2) 0.0182(4) Uani 1 1 d . . .
H10 H 0.4660 0.4670 0.0946 0.022 Uiso 1 1 calc R . .
C1' C 0.0626(2) 0.13559(13) 0.8295(2) 0.0148(4) Uani 1 1 d . . .
H1' H -0.0304 0.1499 0.8488 0.018 Uiso 1 1 calc R . .
C16' C -0.0039(2) 0.17399(12) 0.6037(2) 0.0141(4) Uani 1 1 d . . .
C5' C 0.0571(2) 0.30645(13) 0.87384(19) 0.0157(4) Uani 1 1 d . . .
C3' C 0.1576(3) 0.20507(15) 1.0260(2) 0.0242(5) Uani 1 1 d . . .
H3' H 0.2211 0.2067 1.0999 0.029 Uiso 1 1 calc R . .
C13 C 0.5555(2) 0.44964(12) 0.5737(2) 0.0131(4) Uani 1 1 d . . .
C2' C 0.1639(2) 0.14622(14) 0.9497(2) 0.0205(5) Uani 1 1 d . . .
H2' H 0.2335 0.1098 0.9709 0.025 Uiso 1 1 calc R . .
C19 C 0.6869(2) 0.36623(13) 0.9807(2) 0.0162(4) Uani 1 1 d . . .
H19 H 0.7749 0.3588 1.0273 0.019 Uiso 1 1 calc R . .
C4' C 0.0545(2) 0.26915(17) 1.0007(2) 0.0234(5) Uani 1 1 d . . .
H4'A H 0.0750 0.3074 1.0661 0.028 Uiso 1 1 calc R . .
H4'B H -0.0391 0.2497 1.0046 0.028 Uiso 1 1 calc R . .
C3 C 0.5507(2) 0.62385(13) 0.6686(2) 0.0167(4) Uani 1 1 d . . .
H3 H 0.5986 0.6682 0.6960 0.020 Uiso 1 1 calc R . .
C1 C 0.5152(2) 0.48373(12) 0.6990(2) 0.0120(4) Uani 1 1 d . . .
H1 H 0.4143 0.4943 0.6834 0.014 Uiso 1 1 calc R . .
C14 C 0.7131(2) 0.43131(13) 0.5785(2) 0.0163(4) Uani 1 1 d . . .
H14A H 0.7458 0.4460 0.5006 0.020 Uiso 1 1 calc R . .
H14B H 0.7684 0.4579 0.6478 0.020 Uiso 1 1 calc R . .
C15 C 0.7229(3) 0.34456(14) 0.5976(2) 0.0234(5) Uani 1 1 d . . .
H15A H 0.7851 0.3223 0.5439 0.028 Uiso 1 1 calc R . .
H15B H 0.7587 0.3325 0.6844 0.028 Uiso 1 1 calc R . .
C7' C 0.0422(2) 0.45335(14) 0.9189(2) 0.0216(5) Uani 1 1 d . . .
H7' H 0.0327 0.4503 1.0037 0.026 Uiso 1 1 calc R . .
C19' C 0.1551(3) -0.06877(14) 0.7399(2) 0.0234(5) Uani 1 1 d . . .
H19' H 0.2340 -0.0988 0.7360 0.028 Uiso 1 1 calc R . .
C8' C 0.0477(3) 0.52393(14) 0.8600(3) 0.0259(5) Uani 1 1 d . . .
H8' H 0.0418 0.5683 0.9064 0.031 Uiso 1 1 calc R . .
C9' C 0.0619(3) 0.52941(14) 0.7322(3) 0.0250(5) Uani 1 1 d . . .
H9' H 0.0649 0.5773 0.6954 0.030 Uiso 1 1 calc R . .
C15' C 0.2149(3) 0.1460(3) 0.5570(3) 0.0581(11) Uani 1 1 d . . .
H15C H 0.2659 0.1729 0.4988 0.070 Uiso 1 1 calc R . .
H15D H 0.2457 0.0932 0.5614 0.070 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
Br1' C20' 1.895(3) . ?
Br1 C20 1.899(2) . ?
O1 C11 1.374(3) . ?
O1 C12 1.392(3) . ?
O3' C16' 1.193(3) . ?
O3 C16 1.195(3) . ?
O1' C11' 1.366(3) . ?
O1' C12' 1.388(3) . ?
O2 C16 1.341(3) . ?
O2 C15 1.450(3) . ?
C17 C18 1.394(3) . ?
C17 C22 1.396(3) . ?
C17 C1 1.514(3) . ?
O2' C16' 1.330(3) . ?
O2' C15' 1.443(4) . ?
C11' C10' 1.385(3) . ?
C11' C6' 1.400(3) . ?
C10' C9' 1.388(4) . ?
C18 C19 1.390(3) . ?
C21 C20 1.378(3) . ?
C21 C22 1.389(3) . ?
C2 C3 1.327(3) . ?
C2 C1 1.514(3) . ?
C20 C19 1.385(3) . ?
C4 C3 1.500(3) . ?
C4 C5 1.515(3) . ?
C7 C8 1.388(3) . ?
C7 C6 1.397(3) . ?
C13' C12' 1.493(3) . ?
C13' C16' 1.540(3) . ?
C13' C14' 1.548(3) . ?
C13' C1' 1.565(3) . ?
C17' C22' 1.389(3) . ?
C17' C18' 1.400(3) . ?
C17' C1' 1.524(3) . ?
C12' C5' 1.358(3) . ?
C21' C22' 1.393(3) . ?
C21' C20' 1.395(3) . ?
C5 C12 1.349(3) . ?
C5 C6 1.451(3) . ?
C20' C19' 1.377(4) . ?
C14' C15' 1.483(4) . ?
C16 C13 1.537(3) . ?
C8 C9 1.404(4) . ?
C12 C13 1.494(3) . ?
C6 C11 1.389(3) . ?
C6' C7' 1.398(3) . ?
C6' C5' 1.444(3) . ?
C11 C10 1.389(3) . ?
C9 C10 1.381(3) . ?
C18' C19' 1.397(4) . ?
C1' C2' 1.514(3) . ?
C5' C4' 1.514(3) . ?
C3' C2' 1.324(4) . ?
C3' C4' 1.497(4) . ?
C13 C14 1.544(3) . ?
C13 C1 1.570(3) . ?
C14 C15 1.534(3) . ?
C7' C8' 1.393(4) . ?
C8' C9' 1.401(4) . ?

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
C11 O1 C12 105.78(16) . . ?
C11' O1' C12' 106.35(17) . . ?
C16 O2 C15 112.37(17) . . ?
C18 C17 C22 117.7(2) . . ?
C18 C17 C1 122.76(19) . . ?
C22 C17 C1 119.49(19) . . ?
C16' O2' C15' 111.10(19) . . ?
O1' C11' C10' 126.0(2) . . ?
O1' C11' C6' 109.9(2) . . ?
C10' C11' C6' 124.0(2) . . ?
C11' C10' C9' 116.4(2) . . ?
C19 C18 C17 121.5(2) . . ?
C20 C21 C22 119.0(2) . . ?
C21 C22 C17 121.6(2) . . ?
C3 C2 C1 123.6(2) . . ?
C21 C20 C19 121.3(2) . . ?
C21 C20 Br1 119.21(17) . . ?
C19 C20 Br1 119.45(17) . . ?
C3 C4 C5 112.87(19) . . ?
C8 C7 C6 118.2(2) . . ?
C12' C13' C16' 108.98(17) . . ?
C12' C13' C14' 111.55(18) . . ?
C16' C13' C14' 102.97(18) . . ?
C12' C13' C1' 109.63(17) . . ?
C16' C13' C1' 107.87(17) . . ?
C14' C13' C1' 115.44(18) . . ?
C22' C17' C18' 118.4(2) . . ?
C22' C17' C1' 119.09(19) . . ?
C18' C17' C1' 122.5(2) . . ?
C5' C12' O1' 111.8(2) . . ?
C5' C12' C13' 134.7(2) . . ?
O1' C12' C13' 113.44(17) . . ?
C22' C21' C20' 118.5(2) . . ?
C12 C5 C6 105.73(18) . . ?
C12 C5 C4 128.7(2) . . ?
C6 C5 C4 125.55(19) . . ?
C17' C22' C21' 121.7(2) . . ?
C19' C20' C21' 121.2(2) . . ?
C19' C20' Br1' 119.26(17) . . ?
C21' C20' Br1' 119.57(19) . . ?
C15' C14' C13' 104.7(2) . . ?
O3 C16 O2 122.6(2) . . ?
O3 C16 C13 126.8(2) . . ?
O2 C16 C13 110.61(19) . . ?
C7 C8 C9 121.2(2) . . ?
C5 C12 O1 112.03(18) . . ?
C5 C12 C13 134.8(2) . . ?
O1 C12 C13 113.08(17) . . ?
C11 C6 C7 119.0(2) . . ?
C11 C6 C5 106.25(18) . . ?
C7 C6 C5 134.7(2) . . ?
C7' C6' C11' 118.6(2) . . ?
C7' C6' C5' 135.0(2) . . ?
C11' C6' C5' 106.32(19) . . ?
O1 C11 C10 125.9(2) . . ?
O1 C11 C6 110.19(18) . . ?
C10 C11 C6 123.9(2) . . ?
C10 C9 C8 121.5(2) . . ?
C19' C18' C17' 120.7(2) . . ?
C9 C10 C11 116.1(2) . . ?
C2' C1' C17' 112.92(19) . . ?
C2' C1' C13' 111.02(18) . . ?
C17' C1' C13' 112.78(18) . . ?
O3' C16' O2' 122.3(2) . . ?
O3' C16' C13' 126.7(2) . . ?
O2' C16' C13' 110.91(19) . . ?
C12' C5' C6' 105.66(19) . . ?
C12' C5' C4' 127.7(2) . . ?
C6' C5' C4' 126.5(2) . . ?
C2' C3' C4' 124.0(2) . . ?
C12 C13 C16 108.92(17) . . ?
C12 C13 C14 112.12(18) . . ?
C16 C13 C14 103.25(17) . . ?
C12 C13 C1 109.68(17) . . ?
C16 C13 C1 108.17(17) . . ?
C14 C13 C1 114.35(17) . . ?
C3' C2' C1' 122.9(2) . . ?
C20 C19 C18 118.9(2) . . ?
C3' C4' C5' 113.03(19) . . ?
C2 C3 C4 124.3(2) . . ?
C2 C1 C17 112.61(18) . . ?
C2 C1 C13 110.94(17) . . ?
C17 C1 C13 112.84(17) . . ?
C15 C14 C13 104.60(18) . . ?
O2 C15 C14 106.18(18) . . ?
C8' C7' C6' 118.4(2) . . ?
C20' C19' C18' 119.5(2) . . ?
C7' C8' C9' 121.4(2) . . ?
C10' C9' C8' 121.2(2) . . ?
O2' C15' C14' 109.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        74.56
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_cu_16er007_0m
_database_code_depnum_ccdc_archive 'CCDC 1533672'
_audit_update_record             
;
2017-02-20 deposited with the CCDC.
2017-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(S)-3-(benzofuran-2-yl)-3-((S)-1-(2,4-dichlorophenyl)allyl)dihydrofuran-2(3H)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 Cl2 O3'
_chemical_formula_weight         387.24

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'
O O 0.0492 0.0322 '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'

_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                   8.430(5)
_cell_length_b                   14.204(5)
_cell_length_c                   14.905(5)
_cell_angle_alpha                90.000(0)
_cell_angle_beta                 90.000(0)
_cell_angle_gamma                90.000(0)
_cell_volume                     1784.7(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9676
_cell_measurement_theta_min      4.30
_cell_measurement_theta_max      74.62

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    3.427
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         microsource
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  CMOS
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            36028
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.30
_diffrn_reflns_theta_max         74.62
_reflns_number_total             3662
_reflns_number_gt                3573
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0227P)²+0.6773P] 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   0.078(9)
_refine_ls_number_reflns         3662
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0237
_refine_ls_wR_factor_ref         0.0566
_refine_ls_wR_factor_gt          0.0562
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_chemical_absolute_configuration ad

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 0.76528(4) 0.25538(3) 0.39165(3) 0.02493(10) Uani 1 1 d . . .
Cl2 Cl 1.37903(4) 0.15810(3) 0.38500(3) 0.02063(9) Uani 1 1 d . . .
O1 O 0.67503(12) 0.20221(7) 0.16691(7) 0.0138(2) Uani 1 1 d . . .
O3 O 0.51103(13) 0.39879(8) 0.14601(7) 0.0160(2) Uani 1 1 d . . .
O2 O 0.62775(13) 0.43609(8) 0.01687(7) 0.0177(2) Uani 1 1 d . . .
C8 C 0.76634(16) 0.24797(10) 0.10328(9) 0.0125(3) Uani 1 1 d . . .
C7 C 0.81457(18) 0.18921(10) 0.03802(10) 0.0132(3) Uani 1 1 d . . .
H7 H 0.8765 0.2047 -0.0115 0.016 Uiso 1 1 calc R . .
C18 C 1.24040(18) 0.26106(10) 0.25323(10) 0.0159(3) Uani 1 1 d . . .
H18 H 1.3381 0.2602 0.2243 0.019 Uiso 1 1 calc R . .
C5 C 0.75631(19) 0.00787(11) 0.02054(10) 0.0161(3) Uani 1 1 d . . .
H5 H 0.8110 -0.0027 -0.0327 0.019 Uiso 1 1 calc R . .
C16 C 1.07311(18) 0.21230(11) 0.37603(11) 0.0160(3) Uani 1 1 d . . .
H16 H 1.0593 0.1797 0.4296 0.019 Uiso 1 1 calc R . .
C6 C 0.75162(18) 0.09739(10) 0.05966(9) 0.0128(3) Uani 1 1 d . . .
C17 C 1.21897(18) 0.21414(10) 0.33373(11) 0.0150(3) Uani 1 1 d . . .
C15 C 0.94780(17) 0.26025(11) 0.33676(10) 0.0145(3) Uani 1 1 d . . .
C12 C 0.62664(18) 0.39774(10) 0.09900(10) 0.0125(3) Uani 1 1 d . . .
C14 C 0.96371(17) 0.31060(10) 0.25681(10) 0.0120(3) Uani 1 1 d . . .
C1 C 0.66748(17) 0.10939(10) 0.13934(10) 0.0126(3) Uani 1 1 d . . .
C13 C 0.82895(18) 0.37029(10) 0.22078(10) 0.0112(3) Uani 1 1 d . . .
C9 C 0.78869(16) 0.35156(10) 0.11995(10) 0.0117(3) Uani 1 1 d . . .
C2 C 0.58853(18) 0.03857(12) 0.18401(11) 0.0169(3) Uani 1 1 d . . .
H2 H 0.5348 0.0492 0.2376 0.020 Uiso 1 1 calc R . .
C3 C 0.59433(18) -0.04978(11) 0.14398(11) 0.0174(3) Uani 1 1 d . . .
H3 H 0.5423 -0.1000 0.1711 0.021 Uiso 1 1 calc R . .
C10 C 0.89530(19) 0.39704(12) 0.04922(10) 0.0167(3) Uani 1 1 d . . .
H10A H 0.9481 0.4523 0.0732 0.020 Uiso 1 1 calc R . .
H10B H 0.9748 0.3529 0.0280 0.020 Uiso 1 1 calc R . .
C20 C 0.85244(19) 0.47452(11) 0.23833(10) 0.0156(3) Uani 1 1 d . . .
C4 C 0.67683(19) -0.06459(11) 0.06379(11) 0.0175(3) Uani 1 1 d . . .
H4 H 0.6784 -0.1246 0.0388 0.021 Uiso 1 1 calc R . .
C21 C 0.9696(2) 0.51372(11) 0.28315(11) 0.0204(3) Uani 1 1 d . . .
H21A H 1.0490 0.4764 0.3079 0.024 Uiso 1 1 calc R . .
H21B H 0.9729 0.5788 0.2901 0.024 Uiso 1 1 calc R . .
C19 C 1.11260(19) 0.30947(11) 0.21661(10) 0.0155(3) Uani 1 1 d . . .
H19 H 1.1272 0.3423 0.1633 0.019 Uiso 1 1 calc R . .
C11 C 0.7812(2) 0.42390(12) -0.02599(10) 0.0208(3) Uani 1 1 d . . .
H11A H 0.8148 0.4819 -0.0547 0.025 Uiso 1 1 calc R . .
H11B H 0.7764 0.3745 -0.0709 0.025 Uiso 1 1 calc R . .
H13 H 0.732(2) 0.3535(11) 0.2514(11) 0.004(4) Uiso 1 1 d . . .
H20 H 0.770(2) 0.5140(13) 0.2158(12) 0.016(4) Uiso 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
Cl1 C15 1.7440(17) . ?
Cl2 C17 1.7430(16) . ?
O1 C1 1.3825(18) . ?
O1 C8 1.3837(17) . ?
O3 C12 1.2004(19) . ?
O2 C12 1.3399(18) . ?
O2 C11 1.453(2) . ?
C8 C7 1.345(2) . ?
C8 C9 1.5040(19) . ?
C7 C6 1.445(2) . ?
C18 C17 1.384(2) . ?
C18 C19 1.390(2) . ?
C5 C4 1.387(2) . ?
C5 C6 1.399(2) . ?
C16 C17 1.382(2) . ?
C16 C15 1.386(2) . ?
C6 C1 1.394(2) . ?
C15 C14 1.396(2) . ?
C12 C9 1.547(2) . ?
C14 C19 1.391(2) . ?
C14 C13 1.516(2) . ?
C1 C2 1.378(2) . ?
C13 C20 1.516(2) . ?
C13 C9 1.564(2) . ?
C9 C10 1.529(2) . ?
C2 C3 1.390(2) . ?
C3 C4 1.399(2) . ?
C10 C11 1.526(2) . ?
C20 C21 1.316(2) . ?

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 O1 C8 105.66(11) . . ?
C12 O2 C11 111.07(12) . . ?
C7 C8 O1 111.87(12) . . ?
C7 C8 C9 133.54(13) . . ?
O1 C8 C9 114.58(12) . . ?
C8 C7 C6 106.73(13) . . ?
C17 C18 C19 118.52(14) . . ?
C4 C5 C6 117.84(14) . . ?
C17 C16 C15 118.43(14) . . ?
C1 C6 C5 118.72(14) . . ?
C1 C6 C7 105.48(13) . . ?
C5 C6 C7 135.80(14) . . ?
C16 C17 C18 121.37(14) . . ?
C16 C17 Cl2 118.70(12) . . ?
C18 C17 Cl2 119.92(12) . . ?
C16 C15 C14 122.60(14) . . ?
C16 C15 Cl1 117.04(12) . . ?
C14 C15 Cl1 120.36(12) . . ?
O3 C12 O2 122.27(14) . . ?
O3 C12 C9 127.18(13) . . ?
O2 C12 C9 110.52(12) . . ?
C19 C14 C15 116.64(13) . . ?
C19 C14 C13 122.01(14) . . ?
C15 C14 C13 121.13(13) . . ?
C2 C1 O1 125.10(14) . . ?
C2 C1 C6 124.63(14) . . ?
O1 C1 C6 110.27(13) . . ?
C14 C13 C20 112.78(13) . . ?
C14 C13 C9 114.08(12) . . ?
C20 C13 C9 111.12(12) . . ?
C8 C9 C10 111.91(12) . . ?
C8 C9 C12 105.71(11) . . ?
C10 C9 C12 101.58(12) . . ?
C8 C9 C13 110.65(11) . . ?
C10 C9 C13 117.60(12) . . ?
C12 C9 C13 108.27(11) . . ?
C1 C2 C3 115.76(14) . . ?
C2 C3 C4 121.33(14) . . ?
C11 C10 C9 103.99(13) . . ?
C21 C20 C13 126.78(14) . . ?
C5 C4 C3 121.71(15) . . ?
C18 C19 C14 122.42(14) . . ?
O2 C11 C10 105.54(12) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        74.62
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_cu_16er006_0m
_database_code_depnum_ccdc_archive 'CCDC 1533735'
_audit_update_record             
;
2017-02-20 deposited with the CCDC.
2017-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        22
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 Cl2 O3'
_chemical_formula_weight         391.27

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'
O O 0.0492 0.0322 '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'

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

_cell_length_a                   8.2980(2)
_cell_length_b                   10.5377(3)
_cell_length_c                   21.5903(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1887.90(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9924
_cell_measurement_theta_min      4.10
_cell_measurement_theta_max      74.41

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    3.240
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         microsource
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  CMOS
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            43537
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.10
_diffrn_reflns_theta_max         74.50
_reflns_number_total             3844
_reflns_number_gt                3779
_reflns_threshold_expression     >2sigma(I)

_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, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0268P)²+0.4170P] 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   0.075(8)
_refine_ls_number_reflns         3844
_refine_ls_number_parameters     251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0209
_refine_ls_R_factor_gt           0.0204
_refine_ls_wR_factor_ref         0.0533
_refine_ls_wR_factor_gt          0.0529
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_chemical_absolute_configuration ad

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 0.75652(4) 0.30455(3) 0.351762(14) 0.02081(7) Uani 1 1 d . . .
Cl2 Cl 0.61994(5) 0.46325(3) 0.120738(15) 0.02813(8) Uani 1 1 d . . .
O1 O 0.17500(11) 0.66265(8) 0.40862(4) 0.01816(19) Uani 1 1 d . . .
O2 O 0.37906(12) 0.37195(10) 0.51443(4) 0.0225(2) Uani 1 1 d . . .
O3 O 0.18731(12) 0.19486(10) 0.46681(5) 0.0233(2) Uani 1 1 d . . .
C8 C 0.19486(15) 0.54406(12) 0.38109(6) 0.0155(2) Uani 1 1 d . . .
C1 C 0.05467(15) 0.72300(12) 0.37584(6) 0.0167(2) Uani 1 1 d . . .
C7 C 0.09270(15) 0.52978(12) 0.33299(5) 0.0165(2) Uani 1 1 d . . .
H7 H 0.0833 0.4573 0.3071 0.020 Uiso 1 1 calc R . .
C12 C 0.46711(15) 0.57703(12) 0.28637(6) 0.0186(3) Uani 1 1 d . . .
H12 H 0.3980 0.6416 0.3018 0.022 Uiso 1 1 calc R . .
C11 C 0.53912(14) 0.49354(11) 0.32837(6) 0.0155(2) Uani 1 1 d . . .
C6 C 0.00043(15) 0.64545(12) 0.32827(6) 0.0164(2) Uani 1 1 d . . .
C13 C 0.49288(16) 0.56906(12) 0.22304(6) 0.0197(3) Uani 1 1 d . . .
H13 H 0.4408 0.6262 0.1955 0.024 Uiso 1 1 calc R . .
C15 C 0.67853(15) 0.39641(11) 0.24009(6) 0.0183(3) Uani 1 1 d . . .
H15 H 0.7538 0.3364 0.2245 0.022 Uiso 1 1 calc R . .
C18 C 0.30119(14) 0.32314(11) 0.38536(6) 0.0163(2) Uani 1 1 d . . .
H18A H 0.2979 0.3276 0.3396 0.020 Uiso 1 1 calc R . .
H18B H 0.3989 0.2747 0.3969 0.020 Uiso 1 1 calc R . .
C16 C 0.64833(14) 0.40629(11) 0.30350(6) 0.0162(2) Uani 1 1 d . . .
C14 C 0.59556(16) 0.47663(12) 0.20057(6) 0.0193(3) Uani 1 1 d . . .
C9 C 0.31982(15) 0.46005(12) 0.41063(6) 0.0152(2) Uani 1 1 d . . .
C5 C -0.12295(16) 0.69091(13) 0.28934(6) 0.0201(2) Uani 1 1 d . . .
H5 H -0.1625 0.6410 0.2560 0.024 Uiso 1 1 calc R . .
C10 C 0.49902(16) 0.50184(12) 0.39682(6) 0.0165(2) Uani 1 1 d . . .
C4 C -0.18481(16) 0.81048(13) 0.30106(6) 0.0217(3) Uani 1 1 d . . .
H4 H -0.2688 0.8421 0.2755 0.026 Uiso 1 1 calc R . .
C17 C 0.29047(15) 0.46599(13) 0.48142(6) 0.0183(3) Uani 1 1 d . . .
H17A H 0.3216 0.5510 0.4968 0.022 Uiso 1 1 calc R . .
H17B H 0.1741 0.4544 0.4897 0.022 Uiso 1 1 calc R . .
C2 C -0.00469(17) 0.84352(13) 0.38801(6) 0.0220(3) Uani 1 1 d . . .
H2 H 0.0361 0.8942 0.4209 0.026 Uiso 1 1 calc R . .
C19 C 0.15518(16) 0.24879(12) 0.40701(6) 0.0201(3) Uani 1 1 d . . .
H19A H 0.0604 0.3057 0.4095 0.024 Uiso 1 1 calc R . .
H19B H 0.1307 0.1804 0.3770 0.024 Uiso 1 1 calc R . .
C3 C -0.12733(17) 0.88584(13) 0.34937(6) 0.0233(3) Uani 1 1 d . . .
H3 H -0.1728 0.9675 0.3560 0.028 Uiso 1 1 calc R . .
C20 C 0.54658(18) 0.63051(14) 0.42153(7) 0.0230(3) Uani 1 1 d . . .
C21 C 0.67000(19) 0.64704(17) 0.45943(7) 0.0323(3) Uani 1 1 d . . .
H21A H 0.7327 0.5763 0.4722 0.039 Uiso 1 1 calc R . .
H21B H 0.6959 0.7297 0.4739 0.039 Uiso 1 1 calc R . .
H10 H 0.5630(19) 0.4409(15) 0.4175(7) 0.017(4) Uiso 1 1 d . . .
H20 H 0.489(2) 0.7008(17) 0.4070(8) 0.029(4) Uiso 1 1 d . . .
H2O H 0.336(3) 0.300(2) 0.5084(9) 0.042(6) Uiso 1 1 d . . .
H3O H 0.102(3) 0.1706(19) 0.4775(9) 0.036(5) Uiso 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
Cl1 C16 1.7439(12) . ?
Cl2 C14 1.7411(13) . ?
O1 C1 1.3793(15) . ?
O1 C8 1.3936(15) . ?
O2 C17 1.4250(16) . ?
O3 C19 1.4357(16) . ?
C8 C7 1.3490(17) . ?
C8 C9 1.5052(16) . ?
C1 C2 1.3873(18) . ?
C1 C6 1.3875(18) . ?
C7 C6 1.4430(18) . ?
C12 C13 1.3865(19) . ?
C12 C11 1.3976(18) . ?
C11 C16 1.3982(17) . ?
C11 C10 1.5173(18) . ?
C6 C5 1.4086(18) . ?
C13 C14 1.3820(19) . ?
C15 C14 1.3845(19) . ?
C15 C16 1.3956(19) . ?
C18 C19 1.5166(17) . ?
C18 C9 1.5502(17) . ?
C9 C17 1.5488(17) . ?
C9 C10 1.5793(17) . ?
C5 C4 1.384(2) . ?
C10 C20 1.5095(18) . ?
C4 C3 1.395(2) . ?
C2 C3 1.3895(19) . ?
C20 C21 1.322(2) . ?

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 O1 C8 106.27(9) . . ?
C7 C8 O1 110.74(11) . . ?
C7 C8 C9 133.91(11) . . ?
O1 C8 C9 115.34(10) . . ?
O1 C1 C2 125.59(12) . . ?
O1 C1 C6 110.07(11) . . ?
C2 C1 C6 124.35(12) . . ?
C8 C7 C6 107.07(11) . . ?
C13 C12 C11 122.39(12) . . ?
C12 C11 C16 116.23(12) . . ?
C12 C11 C10 120.12(11) . . ?
C16 C11 C10 123.65(11) . . ?
C1 C6 C5 118.50(12) . . ?
C1 C6 C7 105.85(11) . . ?
C5 C6 C7 135.64(12) . . ?
C14 C13 C12 118.95(12) . . ?
C14 C15 C16 118.02(12) . . ?
C19 C18 C9 116.87(11) . . ?
C15 C16 C11 122.83(12) . . ?
C15 C16 Cl1 116.61(9) . . ?
C11 C16 Cl1 120.56(10) . . ?
C13 C14 C15 121.37(12) . . ?
C13 C14 Cl2 118.44(10) . . ?
C15 C14 Cl2 120.19(10) . . ?
C8 C9 C17 106.62(10) . . ?
C8 C9 C18 109.24(10) . . ?
C17 C9 C18 111.67(10) . . ?
C8 C9 C10 113.87(10) . . ?
C17 C9 C10 108.85(10) . . ?
C18 C9 C10 106.67(10) . . ?
C4 C5 C6 118.05(12) . . ?
C20 C10 C11 109.80(10) . . ?
C20 C10 C9 115.46(11) . . ?
C11 C10 C9 111.98(10) . . ?
C5 C4 C3 121.88(12) . . ?
O2 C17 C9 112.61(10) . . ?
C1 C2 C3 116.11(12) . . ?
O3 C19 C18 109.47(10) . . ?
C2 C3 C4 121.11(12) . . ?
C21 C20 C10 122.65(15) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        74.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.035
