# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

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

data_150730tanaka04
_database_code_depnum_ccdc_archive 'CCDC 1440502'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2016-02-15 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C25 H21 Br O8 S'
_chemical_formula_moiety         'C25 H21 Br O8 S'
_chemical_formula_weight         561.40
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   11.1283(3)
_cell_length_b                   29.5193(7)
_cell_length_c                   7.79325(19)
_cell_angle_alpha                90.0000
_cell_angle_beta                 108.3070(17)
_cell_angle_gamma                90.0000
_cell_volume                     2430.51(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9574
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      68.15
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1144.00
_exptl_absorpt_coefficient_mu    3.535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.564
_exptl_absorpt_correction_T_max  0.965

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            26111
_diffrn_reflns_av_R_equivalents  0.2105
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_full        68.24
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             4455
_reflns_number_gt                1572
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.1210
_refine_ls_wR_factor_ref         0.3993
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4455
_refine_ls_number_parameters     317
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1860P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.070
_refine_diff_density_min         -0.940
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0012(5)

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Br Br -0.6763 1.2805
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.82266(15) 0.49745(5) -0.5684(2) 0.0735(7) Uani 1.0 4 d . . .
S1 S 0.9292(4) 0.55284(11) -0.2149(5) 0.0682(12) Uani 1.0 4 d . . .
O1 O 1.0301(9) 0.6016(3) 0.0998(12) 0.062(3) Uani 1.0 4 d . . .
O2 O 1.4868(9) 0.5967(3) 0.3389(13) 0.075(3) Uani 1.0 4 d . . .
O3 O 1.2630(9) 0.7283(3) 0.0457(13) 0.069(3) Uani 1.0 4 d . . .
O4 O 1.0019(9) 0.6978(3) -0.1928(12) 0.071(3) Uani 1.0 4 d . . .
O5 O 1.0280(9) 0.7111(3) 0.2715(12) 0.066(3) Uani 1.0 4 d . . .
O6 O 0.6982(8) 0.7613(3) 0.0765(12) 0.070(3) Uani 1.0 4 d . . .
O7 O 0.7494(9) 0.7083(3) 0.2889(13) 0.073(3) Uani 1.0 4 d . . .
O8 O 1.1282(9) 0.6647(3) -0.4033(13) 0.078(3) Uani 1.0 4 d . . .
C1 C 1.2589(13) 0.5934(5) 0.2207(18) 0.063(4) Uani 1.0 4 d . . .
C2 C 1.3714(14) 0.6161(5) 0.249(2) 0.070(4) Uani 1.0 4 d . . .
C3 C 1.3797(14) 0.6624(5) 0.1956(18) 0.066(4) Uani 1.0 4 d . . .
C4 C 1.2671(13) 0.6845(5) 0.1031(19) 0.068(4) Uani 1.0 4 d . . .
C5 C 1.1510(13) 0.6622(5) 0.0675(17) 0.061(4) Uani 1.0 4 d . . .
C6 C 1.1521(15) 0.6183(5) 0.135(2) 0.073(5) Uani 1.0 4 d . . .
C7 C 1.0200(12) 0.6785(4) -0.0197(19) 0.062(4) Uani 1.0 4 d . . .
C8 C 0.9653(12) 0.7135(4) 0.0804(16) 0.054(4) Uani 1.0 4 d . . .
C9 C 0.8260(13) 0.6982(5) 0.0364(18) 0.061(4) Uani 1.0 4 d . . .
C10 C 0.8363(12) 0.6463(4) 0.0624(19) 0.060(4) Uani 1.0 4 d . . .
C11 C 0.9425(14) 0.6324(4) -0.022(2) 0.063(4) Uani 1.0 4 d . . .
C12 C 0.7540(13) 0.7221(5) 0.143(3) 0.065(4) Uani 1.0 4 d . . .
C13 C 0.6002(14) 0.6418(6) -0.108(2) 0.074(5) Uani 1.0 4 d . . .
C14 C 0.4879(16) 0.6173(6) -0.163(2) 0.082(5) Uani 1.0 4 d . . .
C15 C 0.4832(15) 0.5724(6) -0.126(2) 0.079(5) Uani 1.0 4 d . . .
C16 C 0.5938(16) 0.5513(5) -0.032(2) 0.079(5) Uani 1.0 4 d . . .
C17 C 0.7074(15) 0.5748(4) 0.0308(18) 0.068(4) Uani 1.0 4 d . . .
C18 C 0.7123(13) 0.6213(5) -0.0048(19) 0.063(4) Uani 1.0 4 d . . .
C19 C 0.8941(14) 0.6103(5) -0.2033(19) 0.063(4) Uani 1.0 4 d . . .
C20 C 0.8182(14) 0.6265(5) -0.364(2) 0.072(5) Uani 1.0 4 d . . .
C21 C 0.7888(14) 0.5920(5) -0.503(2) 0.073(4) Uani 1.0 4 d . . .
C22 C 0.8411(12) 0.5518(4) -0.4397(17) 0.059(4) Uani 1.0 4 d . . .
C23 C 1.3806(15) 0.7508(5) 0.071(3) 0.086(5) Uani 1.0 4 d . . .
C24 C 1.4865(14) 0.5514(5) 0.405(3) 0.080(5) Uani 1.0 4 d . . .
C25 C 1.1427(15) 0.6162(5) -0.410(2) 0.081(5) Uani 1.0 4 d . . .
H1 H 1.2551 0.5629 0.2575 0.0755 Uiso 1.0 4 calc R . .
H3 H 1.4590 0.6774 0.2223 0.0789 Uiso 1.0 4 calc R . .
H4 H 0.9264 0.7063 -0.2368 0.0847 Uiso 1.0 4 calc R . .
H5 H 1.1031 0.7200 0.2945 0.0796 Uiso 1.0 4 calc R . .
H7 H 0.7879 0.6835 0.3134 0.0879 Uiso 1.0 4 calc R . .
H8 H 0.9706 0.7448 0.0337 0.0646 Uiso 1.0 4 calc R . .
H9 H 0.7822 0.7044 -0.0946 0.0736 Uiso 1.0 4 calc R . .
H10 H 0.8710 0.6406 0.1954 0.0715 Uiso 1.0 4 calc R . .
H13 H 0.6005 0.6727 -0.1416 0.0884 Uiso 1.0 4 calc R . .
H14 H 0.4119 0.6324 -0.2287 0.0988 Uiso 1.0 4 calc R . .
H15 H 0.4056 0.5562 -0.1644 0.0951 Uiso 1.0 4 calc R . .
H16 H 0.5929 0.5197 -0.0093 0.0947 Uiso 1.0 4 calc R . .
H17 H 0.7822 0.5594 0.0982 0.0812 Uiso 1.0 4 calc R . .
H20 H 0.7882 0.6568 -0.3827 0.0868 Uiso 1.0 4 calc R . .
H21 H 0.7383 0.5971 -0.6244 0.0875 Uiso 1.0 4 calc R . .
H23A H 1.4274 0.7525 0.2004 0.1027 Uiso 1.0 4 calc R . .
H23B H 1.3647 0.7815 0.0211 0.1027 Uiso 1.0 4 calc R . .
H23C H 1.4306 0.7340 0.0089 0.1027 Uiso 1.0 4 calc R . .
H24A H 1.4370 0.5504 0.4891 0.0964 Uiso 1.0 4 calc R . .
H24B H 1.5736 0.5419 0.4677 0.0964 Uiso 1.0 4 calc R . .
H24C H 1.4486 0.5310 0.3033 0.0964 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Br1 C22 1.870(13) yes . .
S1 C19 1.750(13) yes . .
S1 C22 1.718(12) yes . .
O1 C6 1.388(19) yes . .
O1 C11 1.448(15) yes . .
O2 C2 1.380(17) yes . .
O2 C24 1.431(17) yes . .
O3 C4 1.364(17) yes . .
O3 C23 1.426(18) yes . .
O4 C7 1.420(17) yes . .
O5 C8 1.434(14) yes . .
O6 C12 1.339(17) yes . .
O7 C12 1.23(2) yes . .
O8 C25 1.441(17) yes . .
C1 C2 1.38(2) yes . .
C1 C6 1.379(19) yes . .
C2 C3 1.44(2) yes . .
C3 C4 1.396(19) yes . .
C4 C5 1.40(2) yes . .
C5 C6 1.40(2) yes . .
C5 C7 1.482(18) yes . .
C7 C8 1.53(2) yes . .
C7 C11 1.606(18) yes . .
C8 C9 1.546(19) yes . .
C9 C10 1.546(18) yes . .
C9 C12 1.50(3) yes . .
C10 C11 1.58(3) yes . .
C10 C18 1.505(18) yes . .
C11 C19 1.50(2) yes . .
C13 C14 1.39(3) yes . .
C13 C18 1.393(19) yes . .
C14 C15 1.36(3) yes . .
C15 C16 1.37(2) yes . .
C16 C17 1.39(2) yes . .
C17 C18 1.405(18) yes . .
C19 C20 1.357(19) yes . .
C20 C21 1.45(2) yes . .
C21 C22 1.344(18) yes . .
O4 H4 0.840 no . .
O5 H5 0.840 no . .
O7 H7 0.840 no . .
C1 H1 0.950 no . .
C3 H3 0.950 no . .
C8 H8 1.000 no . .
C9 H9 1.000 no . .
C10 H10 1.000 no . .
C13 H13 0.950 no . .
C14 H14 0.950 no . .
C15 H15 0.950 no . .
C16 H16 0.950 no . .
C17 H17 0.950 no . .
C20 H20 0.950 no . .
C21 H21 0.950 no . .
C23 H23A 0.980 no . .
C23 H23B 0.980 no . .
C23 H23C 0.980 no . .
C24 H24A 0.980 no . .
C24 H24B 0.980 no . .
C24 H24C 0.980 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C19 S1 C22 90.2(6) yes . . .
C6 O1 C11 108.7(10) yes . . .
C2 O2 C24 117.6(11) yes . . .
C4 O3 C23 117.5(10) yes . . .
C2 C1 C6 114.9(13) yes . . .
O2 C2 C1 122.3(13) yes . . .
O2 C2 C3 114.1(13) yes . . .
C1 C2 C3 123.6(13) yes . . .
C2 C3 C4 117.6(13) yes . . .
O3 C4 C3 123.0(13) yes . . .
O3 C4 C5 116.5(12) yes . . .
C3 C4 C5 120.5(13) yes . . .
C4 C5 C6 117.6(12) yes . . .
C4 C5 C7 130.9(13) yes . . .
C6 C5 C7 111.3(13) yes . . .
O1 C6 C1 123.1(13) yes . . .
O1 C6 C5 111.3(12) yes . . .
C1 C6 C5 125.5(15) yes . . .
O4 C7 C5 113.0(13) yes . . .
O4 C7 C8 104.6(9) yes . . .
O4 C7 C11 114.5(10) yes . . .
C5 C7 C8 118.4(11) yes . . .
C5 C7 C11 100.3(10) yes . . .
C8 C7 C11 106.2(12) yes . . .
O5 C8 C7 110.7(10) yes . . .
O5 C8 C9 110.1(11) yes . . .
C7 C8 C9 102.7(10) yes . . .
C8 C9 C10 103.5(10) yes . . .
C8 C9 C12 114.4(11) yes . . .
C10 C9 C12 115.1(13) yes . . .
C9 C10 C11 103.7(11) yes . . .
C9 C10 C18 114.7(10) yes . . .
C11 C10 C18 117.0(11) yes . . .
O1 C11 C7 106.0(10) yes . . .
O1 C11 C10 109.2(12) yes . . .
O1 C11 C19 108.2(10) yes . . .
C7 C11 C10 104.3(10) yes . . .
C7 C11 C19 114.3(13) yes . . .
C10 C11 C19 114.3(12) yes . . .
O6 C12 O7 119.8(15) yes . . .
O6 C12 C9 117.2(14) yes . . .
O7 C12 C9 123.0(13) yes . . .
C14 C13 C18 120.5(14) yes . . .
C13 C14 C15 122.1(14) yes . . .
C14 C15 C16 118.0(15) yes . . .
C15 C16 C17 121.7(14) yes . . .
C16 C17 C18 120.4(13) yes . . .
C10 C18 C13 123.1(12) yes . . .
C10 C18 C17 119.8(12) yes . . .
C13 C18 C17 117.1(13) yes . . .
S1 C19 C11 116.9(9) yes . . .
S1 C19 C20 112.2(11) yes . . .
C11 C19 C20 130.7(12) yes . . .
C19 C20 C21 111.8(12) yes . . .
C20 C21 C22 112.1(12) yes . . .
Br1 C22 S1 119.5(7) yes . . .
Br1 C22 C21 126.8(10) yes . . .
S1 C22 C21 113.6(10) yes . . .
C7 O4 H4 109.472 no . . .
C8 O5 H5 109.478 no . . .
C12 O7 H7 109.474 no . . .
C2 C1 H1 122.576 no . . .
C6 C1 H1 122.571 no . . .
C2 C3 H3 121.182 no . . .
C4 C3 H3 121.179 no . . .
O5 C8 H8 111.019 no . . .
C7 C8 H8 111.028 no . . .
C9 C8 H8 111.018 no . . .
C8 C9 H9 107.850 no . . .
C10 C9 H9 107.840 no . . .
C12 C9 H9 107.833 no . . .
C9 C10 H10 106.950 no . . .
C11 C10 H10 106.964 no . . .
C18 C10 H10 106.963 no . . .
C14 C13 H13 119.741 no . . .
C18 C13 H13 119.734 no . . .
C13 C14 H14 118.933 no . . .
C15 C14 H14 118.952 no . . .
C14 C15 H15 120.989 no . . .
C16 C15 H15 120.980 no . . .
C15 C16 H16 119.150 no . . .
C17 C16 H16 119.156 no . . .
C16 C17 H17 119.777 no . . .
C18 C17 H17 119.784 no . . .
C19 C20 H20 124.106 no . . .
C21 C20 H20 124.118 no . . .
C20 C21 H21 123.922 no . . .
C22 C21 H21 123.934 no . . .
O3 C23 H23A 109.470 no . . .
O3 C23 H23B 109.472 no . . .
O3 C23 H23C 109.468 no . . .
H23A C23 H23B 109.474 no . . .
H23A C23 H23C 109.468 no . . .
H23B C23 H23C 109.475 no . . .
O2 C24 H24A 109.478 no . . .
O2 C24 H24B 109.480 no . . .
O2 C24 H24C 109.478 no . . .
H24A C24 H24B 109.467 no . . .
H24A C24 H24C 109.465 no . . .
H24B C24 H24C 109.459 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C19 S1 C22 Br1 -178.1(10) no . . . .
C19 S1 C22 C21 0.2(11) no . . . .
C22 S1 C19 C11 176.4(11) no . . . .
C22 S1 C19 C20 0.6(11) no . . . .
C6 O1 C11 C7 -14.9(14) no . . . .
C6 O1 C11 C10 -126.8(11) no . . . .
C6 O1 C11 C19 108.2(12) no . . . .
C11 O1 C6 C1 -168.7(13) no . . . .
C11 O1 C6 C5 9.5(16) no . . . .
C24 O2 C2 C1 -1(2) no . . . .
C24 O2 C2 C3 176.8(12) no . . . .
C23 O3 C4 C3 5(2) no . . . .
C23 O3 C4 C5 -176.4(12) no . . . .
C2 C1 C6 O1 -178.0(14) no . . . .
C2 C1 C6 C5 4(3) no . . . .
C6 C1 C2 O2 177.6(14) no . . . .
C6 C1 C2 C3 0(3) no . . . .
O2 C2 C3 C4 179.7(11) no . . . .
C1 C2 C3 C4 -3(3) no . . . .
C2 C3 C4 O3 -179.9(13) no . . . .
C2 C3 C4 C5 1(2) no . . . .
O3 C4 C5 C6 -176.1(11) no . . . .
O3 C4 C5 C7 -2(3) no . . . .
C3 C4 C5 C6 3(2) no . . . .
C3 C4 C5 C7 177.1(13) no . . . .
C4 C5 C6 O1 176.0(13) no . . . .
C4 C5 C6 C1 -6(3) no . . . .
C4 C5 C7 O4 54(2) no . . . .
C4 C5 C7 C8 -69(2) no . . . .
C4 C5 C7 C11 176.3(15) no . . . .
C6 C5 C7 O4 -131.7(12) no . . . .
C6 C5 C7 C8 105.6(14) no . . . .
C6 C5 C7 C11 -9.3(15) no . . . .
C7 C5 C6 O1 0.7(18) no . . . .
C7 C5 C6 C1 178.9(13) no . . . .
O4 C7 C8 O5 -151.4(9) no . . . .
O4 C7 C8 C9 91.1(10) no . . . .
O4 C7 C11 O1 135.7(11) no . . . .
O4 C7 C11 C10 -109.0(12) no . . . .
O4 C7 C11 C19 16.6(16) no . . . .
C5 C7 C8 O5 -24.5(16) no . . . .
C5 C7 C8 C9 -142.0(11) no . . . .
C5 C7 C11 O1 14.3(14) no . . . .
C5 C7 C11 C10 129.6(10) no . . . .
C5 C7 C11 C19 -104.8(12) no . . . .
C8 C7 C11 O1 -109.5(11) no . . . .
C8 C7 C11 C10 5.8(11) no . . . .
C8 C7 C11 C19 131.4(10) no . . . .
C11 C7 C8 O5 87.1(11) no . . . .
C11 C7 C8 C9 -30.4(11) no . . . .
O5 C8 C9 C10 -73.6(11) no . . . .
O5 C8 C9 C12 52.3(13) no . . . .
C7 C8 C9 C10 44.3(11) no . . . .
C7 C8 C9 C12 170.3(9) no . . . .
C8 C9 C10 C11 -40.6(11) no . . . .
C8 C9 C10 C18 -169.3(10) no . . . .
C8 C9 C12 O6 86.8(13) no . . . .
C8 C9 C12 O7 -89.8(15) no . . . .
C10 C9 C12 O6 -153.5(10) no . . . .
C10 C9 C12 O7 29.8(17) no . . . .
C12 C9 C10 C11 -166.1(9) no . . . .
C12 C9 C10 C18 65.2(14) no . . . .
C9 C10 C11 O1 134.1(9) no . . . .
C9 C10 C11 C7 21.1(11) no . . . .
C9 C10 C11 C19 -104.5(10) no . . . .
C9 C10 C18 C13 10(2) no . . . .
C9 C10 C18 C17 -172.4(12) no . . . .
C11 C10 C18 C13 -111.7(14) no . . . .
C11 C10 C18 C17 65.8(17) no . . . .
C18 C10 C11 O1 -98.6(12) no . . . .
C18 C10 C11 C7 148.4(10) no . . . .
C18 C10 C11 C19 22.8(15) no . . . .
O1 C11 C19 S1 10.6(17) no . . . .
O1 C11 C19 C20 -174.4(14) no . . . .
C7 C11 C19 S1 128.5(11) no . . . .
C7 C11 C19 C20 -57(2) no . . . .
C10 C11 C19 S1 -111.3(12) no . . . .
C10 C11 C19 C20 64(2) no . . . .
C14 C13 C18 C10 -178.6(14) no . . . .
C14 C13 C18 C17 4(3) no . . . .
C18 C13 C14 C15 -3(3) no . . . .
C13 C14 C15 C16 -0(3) no . . . .
C14 C15 C16 C17 2(3) no . . . .
C15 C16 C17 C18 -2(3) no . . . .
C16 C17 C18 C10 -179.3(14) no . . . .
C16 C17 C18 C13 -2(3) no . . . .
S1 C19 C20 C21 -1.1(17) no . . . .
C11 C19 C20 C21 -176.3(15) no . . . .
C19 C20 C21 C22 1(2) no . . . .
C20 C21 C22 Br1 177.3(12) no . . . .
C20 C21 C22 S1 -0.8(19) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
S1 O1 2.760(9) no . .
O1 O4 3.594(12) no . .
O1 O5 3.501(12) no . .
O1 C4 3.591(17) no . .
O1 C8 3.374(15) no . .
O1 C9 3.582(16) no . .
O1 C17 3.549(19) no . .
O1 C18 3.420(17) no . .
O3 O4 3.051(12) no . .
O3 C7 2.977(16) no . .
O3 C8 3.435(18) no . .
O4 O5 3.559(14) no . .
O4 C4 3.147(15) no . .
O4 C6 3.484(17) no . .
O4 C9 3.04(2) no . .
O4 C10 3.460(19) no . .
O4 C19 2.839(16) no . .
O4 C20 2.946(16) no . .
O5 O7 3.147(14) no . .
O5 C4 3.41(2) no . .
O5 C5 2.802(18) no . .
O5 C6 3.386(19) no . .
O5 C10 2.947(14) no . .
O5 C11 3.187(16) no . .
O5 C12 2.913(16) no . .
O6 C8 3.281(17) no . .
O7 C8 3.300(19) no . .
O7 C10 2.911(18) no . .
O7 C18 3.377(17) no . .
C1 C4 2.85(2) no . .
C1 C24 2.780(19) no . .
C2 C5 2.773(19) no . .
C3 C6 2.75(3) no . .
C3 C23 2.79(2) no . .
C4 C8 3.42(2) no . .
C5 C10 3.52(2) no . .
C5 C19 3.345(18) no . .
C6 C8 3.44(2) no . .
C6 C10 3.48(2) no . .
C6 C19 3.239(19) no . .
C7 C20 3.287(18) no . .
C9 C13 2.928(19) no . .
C9 C19 3.42(2) no . .
C10 C20 3.32(3) no . .
C11 C17 3.25(3) no . .
C12 C13 3.20(2) no . .
C12 C18 3.17(2) no . .
C13 C16 2.74(3) no . .
C14 C17 2.74(2) no . .
C15 C18 2.82(2) no . .
C17 C19 3.33(3) no . .
C18 C19 2.93(3) no . .
C18 C20 3.36(3) no . .
Br1 C25 3.388(15) no . 3_764
O2 C21 3.198(17) no . 1_656
O3 O5 3.331(12) no . 4_564
O3 O8 3.574(13) no . 4_565
O4 O5 2.727(12) no . 4_564
O4 O6 3.505(12) no . 4_564
O4 O8 2.660(16) no . .
O4 C8 3.112(15) no . 4_564
O4 C12 3.552(16) no . 4_564
O4 C25 3.58(2) no . .
O5 O3 3.331(12) no . 4_565
O5 O4 2.727(12) no . 4_565
O5 O8 2.788(12) no . 1_556
O5 C8 3.506(16) no . 4_565
O6 O4 3.505(12) no . 4_565
O6 O7 2.637(15) no . 4_564
O6 C20 3.546(16) no . 4_565
O6 C23 3.535(19) no . 1_455
O7 O6 2.637(15) no . 4_565
O7 C8 3.582(14) no . 4_565
O7 C9 3.321(16) no . 4_565
O7 C12 3.43(2) no . 4_565
O7 C20 3.527(18) no . 1_556
O8 O3 3.574(13) no . 4_564
O8 O4 2.660(16) no . .
O8 O5 2.788(12) no . 1_554
O8 C5 3.597(17) no . .
O8 C7 3.58(2) no . .
C1 C25 3.57(3) no . 1_556
C5 O8 3.597(17) no . .
C6 C25 3.58(3) no . 1_556
C7 O8 3.58(2) no . .
C8 O4 3.112(15) no . 4_565
C8 O5 3.506(16) no . 4_564
C8 O7 3.582(14) no . 4_564
C9 O7 3.321(16) no . 4_564
C12 O4 3.552(16) no . 4_565
C12 O7 3.43(2) no . 4_564
C17 C21 3.50(2) no . 1_556
C20 O6 3.546(16) no . 4_564
C20 O7 3.527(18) no . 1_554
C21 O2 3.198(17) no . 1_454
C21 C17 3.50(2) no . 1_554
C21 C24 3.43(2) no . 1_454
C23 O6 3.535(19) no . 1_655
C24 C21 3.43(2) no . 1_656
C24 C24 3.35(2) no . 3_866
C25 Br1 3.388(15) no . 3_764
C25 O4 3.58(2) no . .
C25 C1 3.57(3) no . 1_554
C25 C6 3.58(3) no . 1_554
Br1 H21 3.0783 no . .
S1 H17 3.3428 no . .
S1 H20 3.5074 no . .
S1 H21 3.4854 no . .
O1 H1 2.6740 no . .
O1 H10 2.4172 no . .
O1 H17 3.0239 no . .
O2 H1 2.6495 no . .
O2 H3 2.5347 no . .
O3 H3 2.6504 no . .
O3 H5 3.0251 no . .
O3 H8 3.2617 no . .
O4 H8 2.3540 no . .
O4 H9 2.7879 no . .
O4 H20 2.6651 no . .
O5 H7 2.9082 no . .
O5 H9 3.2801 no . .
O5 H10 2.6619 no . .
O6 H7 2.9196 no . .
O6 H8 3.1895 no . .
O6 H9 2.5024 no . .
O6 H13 3.1218 no . .
O7 H9 3.1251 no . .
O7 H10 2.6415 no . .
O7 H13 3.4075 no . .
C1 H3 3.3300 no . .
C1 H24A 2.7034 no . .
C1 H24C 2.7232 no . .
C2 H24A 2.6331 no . .
C2 H24B 3.2188 no . .
C2 H24C 2.6471 no . .
C3 H1 3.3473 no . .
C3 H23A 2.7089 no . .
C3 H23C 2.7232 no . .
C4 H5 2.8912 no . .
C4 H23A 2.6331 no . .
C4 H23B 3.1982 no . .
C4 H23C 2.6119 no . .
C5 H1 3.3247 no . .
C5 H3 3.2869 no . .
C5 H4 3.1374 no . .
C5 H5 2.6293 no . .
C5 H8 3.1149 no . .
C6 H5 3.3582 no . .
C6 H10 3.3714 no . .
C7 H5 2.6327 no . .
C7 H9 2.6375 no . .
C7 H10 2.9250 no . .
C7 H20 3.2378 no . .
C8 H4 2.3815 no . .
C8 H7 3.1984 no . .
C8 H10 2.6700 no . .
C9 H4 2.7076 no . .
C9 H5 3.1740 no . .
C9 H7 2.3673 no . .
C9 H13 2.5685 no . .
C9 H20 3.3876 no . .
C10 H4 3.3245 no . .
C10 H7 2.4457 no . .
C10 H8 3.3082 no . .
C10 H13 2.7203 no . .
C10 H17 2.6699 no . .
C10 H20 3.3543 no . .
C11 H4 2.7214 no . .
C11 H8 3.3454 no . .
C11 H9 2.7156 no . .
C11 H17 3.1239 no . .
C11 H20 2.8884 no . .
C12 H8 2.8757 no . .
C12 H10 2.7046 no . .
C12 H13 2.7519 no . .
C13 H7 3.5161 no . .
C13 H9 2.7179 no . .
C13 H10 3.1942 no . .
C13 H15 3.2666 no . .
C13 H17 3.2508 no . .
C13 H20 3.4579 no . .
C14 H16 3.1990 no . .
C15 H13 3.2541 no . .
C15 H17 3.2593 no . .
C16 H14 3.1996 no . .
C17 H10 2.6948 no . .
C17 H13 3.2516 no . .
C17 H15 3.2695 no . .
C18 H7 2.9849 no . .
C18 H9 2.7283 no . .
C18 H14 3.2654 no . .
C18 H16 3.2778 no . .
C18 H20 3.4710 no . .
C19 H4 2.8793 no . .
C19 H9 3.2614 no . .
C19 H10 3.3197 no . .
C19 H17 3.3421 no . .
C19 H21 3.2170 no . .
C20 H4 2.6895 no . .
C20 H9 3.2210 no . .
C22 H20 3.2102 no . .
C23 H3 2.4908 no . .
C24 H1 2.4920 no . .
H1 H24A 2.2799 no . .
H1 H24B 3.4624 no . .
H1 H24C 2.2746 no . .
H3 H23A 2.2422 no . .
H3 H23B 3.4604 no . .
H3 H23C 2.3076 no . .
H4 H8 2.3069 no . .
H4 H9 2.2183 no . .
H4 H20 2.1674 no . .
H5 H8 2.2266 no . .
H5 H10 3.3923 no . .
H7 H9 3.2199 no . .
H7 H10 1.9590 no . .
H7 H13 3.5182 no . .
H8 H9 2.3454 no . .
H9 H10 2.8680 no . .
H9 H13 2.1511 no . .
H9 H20 2.6666 no . .
H10 H13 3.4486 no . .
H10 H17 2.6130 no . .
H13 H14 2.3215 no . .
H13 H20 3.2523 no . .
H14 H15 2.3100 no . .
H15 H16 2.3218 no . .
H16 H17 2.3247 no . .
H20 H21 2.5095 no . .
Br1 H1 3.3331 no . 3_765
Br1 H15 3.1581 no . 3_664
Br1 H17 3.0917 no . 1_554
Br1 H24A 3.4434 no . 3_765
Br1 H24B 3.1574 no . 1_454
O2 H21 2.7220 no . 1_656
O3 H5 2.6723 no . 4_564
O3 H23B 3.5300 no . 4_565
O4 H5 2.6896 no . 4_564
O4 H8 2.6588 no . 4_564
O5 H4 2.6792 no . 4_565
O5 H8 2.6650 no . 4_565
O6 H4 2.6747 no . 4_565
O6 H7 3.0238 no . 4_564
O6 H9 2.6388 no . 4_565
O6 H13 3.3608 no . 4_565
O6 H20 2.5974 no . 4_565
O6 H23A 3.4516 no . 1_455
O6 H23A 3.5061 no . 4_464
O6 H23C 2.9690 no . 1_455
O7 H3 3.2388 no . 1_455
O7 H4 3.2431 no . 4_565
O7 H8 2.9446 no . 4_565
O7 H9 2.7196 no . 4_565
O7 H20 2.8900 no . 1_556
O7 H21 3.3601 no . 1_556
O8 H4 3.1735 no . .
O8 H5 2.8070 no . 1_554
O8 H8 3.1504 no . 4_564
O8 H10 3.5856 no . 1_554
O8 H14 3.1663 no . 1_655
O8 H23B 3.2823 no . 4_564
C3 H14 3.5478 no . 1_655
C3 H23B 3.0775 no . 4_565
C4 H23B 3.2520 no . 4_565
C7 H5 3.5748 no . 4_564
C8 H4 2.8639 no . 4_565
C9 H4 3.3277 no . 4_565
C10 H21 3.3051 no . 1_556
C12 H4 2.8099 no . 4_565
C12 H8 3.3818 no . 4_565
C12 H9 2.9320 no . 4_565
C12 H23C 3.4359 no . 1_455
C13 H3 3.5713 no . 1_455
C13 H23C 3.5888 no . 1_455
C14 H3 3.5890 no . 1_455
C14 H24A 3.2554 no . 1_454
C15 H16 3.1281 no . 3_665
C15 H24A 2.9508 no . 1_454
C15 H24C 3.5284 no . 3_765
C16 H15 3.5225 no . 3_665
C16 H16 3.0381 no . 3_665
C16 H21 3.3628 no . 1_556
C16 H24A 3.5886 no . 1_454
C16 H24C 3.5298 no . 1_455
C16 H24C 3.1545 no . 3_765
C17 H21 2.6825 no . 1_556
C18 H21 2.9739 no . 1_556
C20 H7 2.9557 no . 1_554
C21 H7 3.0555 no . 1_554
C21 H10 3.1275 no . 1_554
C21 H17 3.2346 no . 1_554
C21 H24B 2.7620 no . 1_454
C22 H17 3.4592 no . 1_554
C22 H24B 2.8492 no . 1_454
C23 H5 3.2774 no . 4_564
C23 H13 3.5569 no . 4_665
C23 H23A 3.0929 no . 4_564
C23 H23C 3.3112 no . 4_565
C24 H21 3.1825 no . 1_656
C24 H24A 3.1635 no . 3_866
C24 H24B 3.0718 no . 3_866
C24 H24C 3.2516 no . 3_866
C25 H1 3.5748 no . 1_554
C25 H14 2.9230 no . 1_655
C25 H15 3.4418 no . 1_655
H1 Br1 3.3331 no . 3_765
H1 C25 3.5748 no . 1_556
H3 O7 3.2388 no . 1_655
H3 C13 3.5713 no . 1_655
H3 C14 3.5890 no . 1_655
H3 H7 3.5072 no . 1_655
H3 H23B 3.0871 no . 4_565
H3 H23C 3.5184 no . 4_565
H4 O5 2.6792 no . 4_564
H4 O6 2.6747 no . 4_564
H4 O7 3.2431 no . 4_564
H4 O8 3.1735 no . .
H4 C8 2.8639 no . 4_564
H4 C9 3.3277 no . 4_564
H4 C12 2.8099 no . 4_564
H4 H5 2.8911 no . 4_564
H4 H7 3.4242 no . 1_554
H4 H8 2.4655 no . 4_564
H5 O3 2.6723 no . 4_565
H5 O4 2.6896 no . 4_565
H5 O8 2.8070 no . 1_556
H5 C7 3.5748 no . 4_565
H5 C23 3.2774 no . 4_565
H5 H4 2.8911 no . 4_565
H5 H8 2.9086 no . 4_565
H5 H23B 2.8925 no . 4_565
H7 O6 3.0238 no . 4_565
H7 C20 2.9557 no . 1_556
H7 C21 3.0555 no . 1_556
H7 H3 3.5072 no . 1_455
H7 H4 3.4242 no . 1_556
H7 H8 3.0621 no . 4_565
H7 H9 3.3924 no . 4_565
H7 H20 2.4948 no . 1_556
H7 H21 2.6838 no . 1_556
H8 O4 2.6588 no . 4_565
H8 O5 2.6650 no . 4_564
H8 O7 2.9446 no . 4_564
H8 O8 3.1504 no . 4_565
H8 C12 3.3818 no . 4_564
H8 H4 2.4655 no . 4_565
H8 H5 2.9086 no . 4_564
H8 H7 3.0621 no . 4_564
H9 O6 2.6388 no . 4_564
H9 O7 2.7196 no . 4_564
H9 C12 2.9320 no . 4_564
H9 H7 3.3924 no . 4_564
H10 O8 3.5856 no . 1_556
H10 C21 3.1275 no . 1_556
H10 H21 2.6649 no . 1_556
H13 O6 3.3608 no . 4_564
H13 C23 3.5569 no . 4_464
H13 H23A 2.9345 no . 4_464
H13 H23B 3.3589 no . 4_464
H13 H23C 3.1003 no . 1_455
H14 O8 3.1663 no . 1_455
H14 C3 3.5478 no . 1_455
H14 C25 2.9230 no . 1_455
H14 H23A 3.4556 no . 4_464
H14 H23B 3.1445 no . 4_464
H14 H23C 3.4948 no . 1_455
H14 H24A 3.3405 no . 1_454
H15 Br1 3.1581 no . 3_664
H15 C16 3.5225 no . 3_665
H15 C25 3.4418 no . 1_455
H15 H16 2.6151 no . 3_665
H15 H24A 2.8352 no . 1_454
H15 H24C 3.3958 no . 3_765
H16 C15 3.1281 no . 3_665
H16 C16 3.0381 no . 3_665
H16 H15 2.6151 no . 3_665
H16 H16 2.4157 no . 3_665
H16 H24C 3.3291 no . 1_455
H16 H24C 2.6515 no . 3_765
H17 Br1 3.0917 no . 1_556
H17 C21 3.2346 no . 1_556
H17 C22 3.4592 no . 1_556
H17 H21 2.6116 no . 1_556
H20 O6 2.5974 no . 4_564
H20 O7 2.8900 no . 1_554
H20 H7 2.4948 no . 1_554
H21 O2 2.7220 no . 1_454
H21 O7 3.3601 no . 1_554
H21 C10 3.3051 no . 1_554
H21 C16 3.3628 no . 1_554
H21 C17 2.6825 no . 1_554
H21 C18 2.9739 no . 1_554
H21 C24 3.1825 no . 1_454
H21 H7 2.6838 no . 1_554
H21 H10 2.6649 no . 1_554
H21 H17 2.6116 no . 1_554
H21 H24B 2.7130 no . 1_454
H23A O6 3.4516 no . 1_655
H23A O6 3.5061 no . 4_665
H23A C23 3.0929 no . 4_565
H23A H13 2.9345 no . 4_665
H23A H14 3.4556 no . 4_665
H23A H23B 2.9724 no . 4_565
H23A H23C 2.4264 no . 4_565
H23B O3 3.5300 no . 4_564
H23B O8 3.2823 no . 4_565
H23B C3 3.0775 no . 4_564
H23B C4 3.2520 no . 4_564
H23B H3 3.0871 no . 4_564
H23B H5 2.8925 no . 4_564
H23B H13 3.3589 no . 4_665
H23B H14 3.1445 no . 4_665
H23B H23A 2.9724 no . 4_564
H23C O6 2.9690 no . 1_655
H23C C12 3.4359 no . 1_655
H23C C13 3.5888 no . 1_655
H23C C23 3.3112 no . 4_564
H23C H3 3.5184 no . 4_564
H23C H13 3.1003 no . 1_655
H23C H14 3.4948 no . 1_655
H23C H23A 2.4264 no . 4_564
H24A Br1 3.4434 no . 3_765
H24A C14 3.2554 no . 1_656
H24A C15 2.9508 no . 1_656
H24A C16 3.5886 no . 1_656
H24A C24 3.1635 no . 3_866
H24A H14 3.3405 no . 1_656
H24A H15 2.8352 no . 1_656
H24A H24A 3.2731 no . 3_866
H24A H24B 2.7534 no . 3_866
H24A H24C 2.9526 no . 3_866
H24B Br1 3.1574 no . 1_656
H24B C21 2.7620 no . 1_656
H24B C22 2.8492 no . 1_656
H24B C24 3.0718 no . 3_866
H24B H21 2.7130 no . 1_656
H24B H24A 2.7534 no . 3_866
H24B H24B 3.0937 no . 3_866
H24B H24C 2.8543 no . 3_866
H24C C15 3.5284 no . 3_765
H24C C16 3.5298 no . 1_655
H24C C16 3.1545 no . 3_765
H24C C24 3.2516 no . 3_866
H24C H15 3.3958 no . 3_765
H24C H16 3.3291 no . 1_655
H24C H16 2.6515 no . 3_765
H24C H24A 2.9526 no . 3_866
H24C H24B 2.8543 no . 3_866
H24C H24C 3.4416 no . 3_866

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        'rocaglamide 23c'
####################################################################### 
# 
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1440504'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2016-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'rocaglamide 22a'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H24 O7 S'
_chemical_formula_weight         468.50

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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pbca '
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'
'-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                   9.8131(3)
_cell_length_b                   20.4457(5)
_cell_length_c                   21.4000(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4293.6(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    173
_cell_measurement_reflns_used    7787
_cell_measurement_theta_min      4.13
_cell_measurement_theta_max      67.58
_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1968
_exptl_absorpt_coefficient_mu    1.744
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3359
_exptl_absorpt_correction_T_max  0.7217
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            14098
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.13
_diffrn_reflns_theta_max         68.11
_reflns_number_total             3851
_reflns_number_gt                3510
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_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)+(0.0672P)²+1.5656P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3851
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.1030
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
C2 C -0.01590(15) 0.25525(7) 0.30174(6) 0.0224(3) Uani 1 1 d . . .
C3 C -0.13777(15) 0.28091(7) 0.32349(7) 0.0243(3) Uani 1 1 d . . .
C4 C -0.20766(15) 0.24901(7) 0.37181(7) 0.0241(3) Uani 1 1 d . . .
C5 C -0.15932(15) 0.19204(7) 0.39916(7) 0.0248(3) Uani 1 1 d . . .
C6 C -0.03463(15) 0.16974(7) 0.37698(7) 0.0226(3) Uani 1 1 d . . .
C7 C 0.03855(14) 0.19951(7) 0.33011(7) 0.0219(3) Uani 1 1 d . . .
C8 C 0.16617(14) 0.16200(7) 0.31690(7) 0.0217(3) Uani 1 1 d . . .
C9 C 0.15487(14) 0.10429(7) 0.36690(7) 0.0212(3) Uani 1 1 d . . .
C10 C 0.17335(16) 0.12828(7) 0.25219(7) 0.0239(3) Uani 1 1 d . . .
C11 C 0.22095(14) 0.05820(7) 0.26689(7) 0.0219(3) Uani 1 1 d . . .
C12 C 0.14274(14) 0.04116(7) 0.32699(6) 0.0212(3) Uani 1 1 d . . .
C13 C 0.17899(14) -0.02174(7) 0.36043(7) 0.0222(3) Uani 1 1 d . . .
C14 C 0.10374(16) -0.03971(8) 0.41311(8) 0.0296(3) Uani 1 1 d . . .
C15 C 0.13153(18) -0.09684(9) 0.44526(8) 0.0353(4) Uani 1 1 d . . .
C16 C 0.23600(18) -0.13745(8) 0.42540(8) 0.0328(4) Uani 1 1 d . . .
C17 C 0.28392(16) -0.06246(7) 0.34157(7) 0.0269(3) Uani 1 1 d . . .
C18 C 0.18885(15) 0.01348(7) 0.21307(7) 0.0247(3) Uani 1 1 d . . .
C19 C 0.2436(2) -0.01229(11) 0.10905(8) 0.0452(5) Uani 1 1 d . . .
H19A H 0.2775 -0.0570 0.1149 0.068 Uiso 1 1 calc R . .
H19B H 0.2896 0.0078 0.0732 0.068 Uiso 1 1 calc R . .
H19C H 0.1452 -0.0134 0.1014 0.068 Uiso 1 1 calc R . .
C20 C 0.26532(15) 0.10426(7) 0.41545(7) 0.0238(3) Uani 1 1 d . . .
C21 C 0.39283(16) 0.07814(8) 0.41485(8) 0.0289(3) Uani 1 1 d . . .
C22 C 0.46652(17) 0.09071(8) 0.47052(8) 0.0327(4) Uani 1 1 d . . .
C23 C 0.39528(19) 0.12677(9) 0.51207(8) 0.0365(4) Uani 1 1 d . . .
C24 C 0.00085(19) 0.33656(8) 0.22227(8) 0.0330(4) Uani 1 1 d . . .
H24A H -0.0890 0.3259 0.2051 0.049 Uiso 1 1 calc R . .
H24B H 0.0617 0.3501 0.1883 0.049 Uiso 1 1 calc R . .
H24C H -0.0080 0.3723 0.2525 0.049 Uiso 1 1 calc R . .
C25 C -0.42284(16) 0.24034(8) 0.42284(8) 0.0339(4) Uani 1 1 d . . .
H25A H -0.4365 0.1985 0.4013 0.051 Uiso 1 1 calc R . .
H25B H -0.5097 0.2639 0.4252 0.051 Uiso 1 1 calc R . .
H25C H -0.3886 0.2322 0.4651 0.051 Uiso 1 1 calc R . .
C26 C 0.31237(18) -0.11982(8) 0.37404(8) 0.0318(4) Uani 1 1 d . . .
H1 H -0.1765(19) 0.3186(9) 0.3047(9) 0.030(4) Uiso 1 1 d . . .
H2 H -0.2105(18) 0.1695(9) 0.4331(9) 0.026(4) Uiso 1 1 d . . .
H3 H 0.3168(18) 0.0590(8) 0.2726(7) 0.018(4) Uiso 1 1 d . . .
H4 H 0.2368(18) 0.1508(8) 0.2264(8) 0.021(4) Uiso 1 1 d . . .
H5 H 0.430(2) 0.0548(10) 0.3805(10) 0.042(5) Uiso 1 1 d . . .
H6 H 0.0502(18) 0.0384(8) 0.3171(8) 0.021(4) Uiso 1 1 d . . .
H7 H 0.031(2) -0.0118(9) 0.4273(9) 0.034(5) Uiso 1 1 d . . .
H8 H 0.387(2) -0.1463(10) 0.3605(10) 0.041(5) Uiso 1 1 d . . .
H9 H 0.341(2) -0.0513(10) 0.3051(10) 0.040(5) Uiso 1 1 d . . .
H10 H 0.078(2) -0.1079(10) 0.4814(10) 0.045(6) Uiso 1 1 d . . .
H11 H 0.256(2) -0.1776(10) 0.4467(9) 0.036(5) Uiso 1 1 d . . .
H12 H 0.556(2) 0.0747(10) 0.4786(10) 0.044(6) Uiso 1 1 d . . .
H13 H 0.416(3) 0.1395(11) 0.5526(12) 0.056(7) Uiso 1 1 d . . .
O1 O 0.02686(10) 0.11492(5) 0.40058(5) 0.0244(2) Uani 1 1 d . . .
O2 O 0.05650(11) 0.27996(5) 0.25278(5) 0.0271(2) Uani 1 1 d . . .
O3 O -0.32639(11) 0.27878(5) 0.38911(5) 0.0300(3) Uani 1 1 d . . .
O4 O 0.28891(11) 0.19892(5) 0.32370(5) 0.0264(2) Uani 1 1 d . . .
H4A H 0.2901 0.2168 0.3591 0.040 Uiso 1 1 calc R . .
O5 O 0.04398(12) 0.12197(5) 0.22279(5) 0.0312(3) Uani 1 1 d . . .
H5A H 0.0109 0.1593 0.2165 0.047 Uiso 1 1 calc R . .
O6 O 0.10027(14) -0.02684(6) 0.21211(5) 0.0404(3) Uani 1 1 d . . .
O7 O 0.27096(12) 0.02558(6) 0.16443(5) 0.0351(3) Uani 1 1 d . . .
S1 S 0.23587(5) 0.14511(2) 0.484644(18) 0.03605(14) 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
C2 O2 1.3630(18) . ?
C2 C3 1.386(2) . ?
C2 C7 1.397(2) . ?
C3 C4 1.402(2) . ?
C3 H1 0.949(19) . ?
C4 O3 1.3656(18) . ?
C4 C5 1.387(2) . ?
C5 C6 1.389(2) . ?
C5 H2 0.996(19) . ?
C6 O1 1.3695(17) . ?
C6 C7 1.376(2) . ?
C7 C8 1.495(2) . ?
C8 O4 1.4289(17) . ?
C8 C10 1.549(2) . ?
C8 C9 1.5967(19) . ?
C9 O1 1.4645(17) . ?
C9 C20 1.501(2) . ?
C9 C12 1.5523(19) . ?
C10 O5 1.4228(19) . ?
C10 C11 1.540(2) . ?
C10 H4 0.951(18) . ?
C11 C18 1.504(2) . ?
C11 C12 1.5377(19) . ?
C11 H3 0.949(18) . ?
C12 C13 1.5142(19) . ?
C12 H6 0.935(17) . ?
C13 C17 1.384(2) . ?
C13 C14 1.397(2) . ?
C14 C15 1.383(2) . ?
C14 H7 0.96(2) . ?
C15 C16 1.386(3) . ?
C15 H10 0.96(2) . ?
C16 C26 1.378(3) . ?
C16 H11 0.96(2) . ?
C17 C26 1.391(2) . ?
C17 H9 0.99(2) . ?
C18 O6 1.1982(19) . ?
C18 O7 1.3394(19) . ?
C19 O7 1.441(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.361(2) . ?
C20 S1 1.7244(15) . ?
C21 C22 1.417(2) . ?
C21 H5 0.95(2) . ?
C22 C23 1.350(3) . ?
C22 H12 0.95(2) . ?
C23 S1 1.7122(19) . ?
C23 H13 0.93(2) . ?
C24 O2 1.4364(18) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 O3 1.426(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H8 0.96(2) . ?
O4 H4A 0.8400 . ?
O5 H5A 0.8400 . ?

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
O2 C2 C3 124.57(13) . . ?
O2 C2 C7 115.91(13) . . ?
C3 C2 C7 119.51(13) . . ?
C2 C3 C4 119.59(14) . . ?
C2 C3 H1 120.7(12) . . ?
C4 C3 H1 119.6(12) . . ?
O3 C4 C5 123.47(14) . . ?
O3 C4 C3 114.21(13) . . ?
C5 C4 C3 122.31(14) . . ?
C4 C5 C6 115.63(14) . . ?
C4 C5 H2 121.6(11) . . ?
C6 C5 H2 122.8(11) . . ?
O1 C6 C7 113.64(12) . . ?
O1 C6 C5 122.05(13) . . ?
C7 C6 C5 124.31(14) . . ?
C6 C7 C2 118.56(13) . . ?
C6 C7 C8 110.37(12) . . ?
C2 C7 C8 131.02(13) . . ?
O4 C8 C7 114.57(12) . . ?
O4 C8 C10 106.73(11) . . ?
C7 C8 C10 115.81(12) . . ?
O4 C8 C9 112.38(11) . . ?
C7 C8 C9 101.20(11) . . ?
C10 C8 C9 105.86(11) . . ?
O1 C9 C20 106.18(11) . . ?
O1 C9 C12 109.17(11) . . ?
C20 C9 C12 115.84(12) . . ?
O1 C9 C8 106.24(10) . . ?
C20 C9 C8 114.44(12) . . ?
C12 C9 C8 104.54(11) . . ?
O5 C10 C11 106.07(12) . . ?
O5 C10 C8 113.28(12) . . ?
C11 C10 C8 104.21(11) . . ?
O5 C10 H4 111.8(10) . . ?
C11 C10 H4 111.7(10) . . ?
C8 C10 H4 109.5(10) . . ?
C18 C11 C12 113.47(12) . . ?
C18 C11 C10 110.23(12) . . ?
C12 C11 C10 103.32(11) . . ?
C18 C11 H3 108.5(10) . . ?
C12 C11 H3 113.1(10) . . ?
C10 C11 H3 108.1(10) . . ?
C13 C12 C11 118.07(12) . . ?
C13 C12 C9 115.35(12) . . ?
C11 C12 C9 103.50(11) . . ?
C13 C12 H6 106.5(10) . . ?
C11 C12 H6 108.0(10) . . ?
C9 C12 H6 104.5(10) . . ?
C17 C13 C14 118.06(14) . . ?
C17 C13 C12 123.22(13) . . ?
C14 C13 C12 118.73(13) . . ?
C15 C14 C13 121.29(15) . . ?
C15 C14 H7 119.2(11) . . ?
C13 C14 H7 119.5(11) . . ?
C14 C15 C16 119.96(16) . . ?
C14 C15 H10 119.4(13) . . ?
C16 C15 H10 120.7(13) . . ?
C26 C16 C15 119.34(15) . . ?
C26 C16 H11 119.5(12) . . ?
C15 C16 H11 121.2(12) . . ?
C13 C17 C26 120.71(15) . . ?
C13 C17 H9 120.8(12) . . ?
C26 C17 H9 118.5(12) . . ?
O6 C18 O7 123.38(14) . . ?
O6 C18 C11 125.69(14) . . ?
O7 C18 C11 110.90(12) . . ?
O7 C19 H19A 109.5 . . ?
O7 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O7 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C9 131.11(14) . . ?
C21 C20 S1 110.63(12) . . ?
C9 C20 S1 118.24(11) . . ?
C20 C21 C22 112.96(15) . . ?
C20 C21 H5 123.9(13) . . ?
C22 C21 H5 123.2(13) . . ?
C23 C22 C21 112.85(15) . . ?
C23 C22 H12 123.0(13) . . ?
C21 C22 H12 124.1(13) . . ?
C22 C23 S1 111.53(13) . . ?
C22 C23 H13 130.9(16) . . ?
S1 C23 H13 117.4(16) . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C16 C26 C17 120.63(16) . . ?
C16 C26 H8 120.7(12) . . ?
C17 C26 H8 118.7(12) . . ?
C6 O1 C9 108.54(10) . . ?
C2 O2 C24 116.74(12) . . ?
C4 O3 C25 117.25(12) . . ?
C8 O4 H4A 109.5 . . ?
C10 O5 H5A 109.5 . . ?
C18 O7 C19 115.33(13) . . ?
C23 S1 C20 92.02(8) . . ?

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
O2 C2 C3 C4 176.09(13) . . . . ?
C7 C2 C3 C4 -2.7(2) . . . . ?
C2 C3 C4 O3 -179.86(13) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
O3 C4 C5 C6 -178.10(13) . . . . ?
C3 C4 C5 C6 2.0(2) . . . . ?
C4 C5 C6 O1 178.59(13) . . . . ?
C4 C5 C6 C7 -1.5(2) . . . . ?
O1 C6 C7 C2 178.78(12) . . . . ?
C5 C6 C7 C2 -1.2(2) . . . . ?
O1 C6 C7 C8 1.19(17) . . . . ?
C5 C6 C7 C8 -178.75(13) . . . . ?
O2 C2 C7 C6 -175.64(12) . . . . ?
C3 C2 C7 C6 3.3(2) . . . . ?
O2 C2 C7 C8 1.4(2) . . . . ?
C3 C2 C7 C8 -179.71(14) . . . . ?
C6 C7 C8 O4 -122.24(13) . . . . ?
C2 C7 C8 O4 60.6(2) . . . . ?
C6 C7 C8 C10 112.82(14) . . . . ?
C2 C7 C8 C10 -64.4(2) . . . . ?
C6 C7 C8 C9 -1.09(15) . . . . ?
C2 C7 C8 C9 -178.28(15) . . . . ?
O4 C8 C9 O1 123.35(12) . . . . ?
C7 C8 C9 O1 0.67(13) . . . . ?
C10 C8 C9 O1 -120.51(12) . . . . ?
O4 C8 C9 C20 6.53(17) . . . . ?
C7 C8 C9 C20 -116.15(13) . . . . ?
C10 C8 C9 C20 122.67(13) . . . . ?
O4 C8 C9 C12 -121.25(12) . . . . ?
C7 C8 C9 C12 116.08(12) . . . . ?
C10 C8 C9 C12 -5.10(14) . . . . ?
O4 C8 C10 O5 -146.23(12) . . . . ?
C7 C8 C10 O5 -17.36(17) . . . . ?
C9 C8 C10 O5 93.85(13) . . . . ?
O4 C8 C10 C11 98.95(12) . . . . ?
C7 C8 C10 C11 -132.17(12) . . . . ?
C9 C8 C10 C11 -20.96(14) . . . . ?
O5 C10 C11 C18 41.39(15) . . . . ?
C8 C10 C11 C18 161.21(12) . . . . ?
O5 C10 C11 C12 -80.16(13) . . . . ?
C8 C10 C11 C12 39.65(14) . . . . ?
C18 C11 C12 C13 68.82(16) . . . . ?
C10 C11 C12 C13 -171.83(12) . . . . ?
C18 C11 C12 C9 -162.35(12) . . . . ?
C10 C11 C12 C9 -43.01(13) . . . . ?
O1 C9 C12 C13 -86.94(14) . . . . ?
C20 C9 C12 C13 32.82(17) . . . . ?
C8 C9 C12 C13 159.73(12) . . . . ?
O1 C9 C12 C11 142.58(11) . . . . ?
C20 C9 C12 C11 -97.66(14) . . . . ?
C8 C9 C12 C11 29.25(13) . . . . ?
C11 C12 C13 C17 3.8(2) . . . . ?
C9 C12 C13 C17 -119.21(15) . . . . ?
C11 C12 C13 C14 -176.48(13) . . . . ?
C9 C12 C13 C14 60.47(18) . . . . ?
C17 C13 C14 C15 -0.8(2) . . . . ?
C12 C13 C14 C15 179.50(15) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C26 0.8(3) . . . . ?
C14 C13 C17 C26 0.5(2) . . . . ?
C12 C13 C17 C26 -179.80(14) . . . . ?
C12 C11 C18 O6 8.9(2) . . . . ?
C10 C11 C18 O6 -106.39(17) . . . . ?
C12 C11 C18 O7 -172.73(12) . . . . ?
C10 C11 C18 O7 71.95(15) . . . . ?
O1 C9 C20 C21 157.50(16) . . . . ?
C12 C9 C20 C21 36.1(2) . . . . ?
C8 C9 C20 C21 -85.65(19) . . . . ?
O1 C9 C20 S1 -24.47(14) . . . . ?
C12 C9 C20 S1 -145.84(11) . . . . ?
C8 C9 C20 S1 92.39(13) . . . . ?
C9 C20 C21 C22 178.58(15) . . . . ?
S1 C20 C21 C22 0.43(18) . . . . ?
C20 C21 C22 C23 -0.9(2) . . . . ?
C21 C22 C23 S1 0.9(2) . . . . ?
C15 C16 C26 C17 -1.1(3) . . . . ?
C13 C17 C26 C16 0.4(2) . . . . ?
C7 C6 O1 C9 -0.69(16) . . . . ?
C5 C6 O1 C9 179.25(13) . . . . ?
C20 C9 O1 C6 122.17(12) . . . . ?
C12 C9 O1 C6 -112.27(12) . . . . ?
C8 C9 O1 C6 -0.05(14) . . . . ?
C3 C2 O2 C24 0.0(2) . . . . ?
C7 C2 O2 C24 178.89(13) . . . . ?
C5 C4 O3 C25 -18.9(2) . . . . ?
C3 C4 O3 C25 160.97(13) . . . . ?
O6 C18 O7 C19 1.7(2) . . . . ?
C11 C18 O7 C19 -176.72(14) . . . . ?
C22 C23 S1 C20 -0.58(14) . . . . ?
C21 C20 S1 C23 0.07(13) . . . . ?
C9 C20 S1 C23 -178.34(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        68.11
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_141213kofuji03
_database_code_depnum_ccdc_archive 'CCDC 1440509'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2016-02-15 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C25 H22 Br Cl3 O8'
_chemical_formula_moiety         'C25 H22 Br Cl3 O8'
_chemical_formula_weight         636.71
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.7833(3)
_cell_length_b                   10.5843(4)
_cell_length_c                   14.6153(5)
_cell_angle_alpha                74.063(2)
_cell_angle_beta                 80.510(2)
_cell_angle_gamma                63.2837(18)
_cell_volume                     1298.37(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3413
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      68.15
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             644.00
_exptl_absorpt_coefficient_mu    5.428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.617
_exptl_absorpt_correction_T_max  0.762

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            13987
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_full        68.24
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             4644
_reflns_number_gt                2939
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1490
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4644
_refine_ls_number_parameters     335
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0000P)²+8.1150P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.770
_refine_diff_density_min         -0.840
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00024(10)

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Br Br -0.6763 1.2805
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.30129(8) 0.95210(8) 0.12294(5) 0.0291(3) Uani 1.0 2 d . . .
Cl31 Cl 0.5945(2) 0.51534(18) 0.32796(13) 0.0364(5) Uani 1.0 2 d . . .
Cl32 Cl 0.5884(3) 0.5153(2) 0.13129(14) 0.0483(6) Uani 1.0 2 d . . .
Cl33 Cl 0.3079(3) 0.5890(2) 0.25108(17) 0.0516(6) Uani 1.0 2 d . . .
O1 O 0.8015(5) 1.1175(5) 0.2059(3) 0.0188(9) Uani 1.0 2 d . . .
O2 O 1.0757(5) 1.2728(5) 0.3639(3) 0.0275(11) Uani 1.0 2 d . . .
O3 O 0.7177(5) 1.0924(5) 0.5314(3) 0.0227(10) Uani 1.0 2 d . . .
O4 O 0.5069(5) 1.1719(5) 0.3418(3) 0.0211(10) Uani 1.0 2 d . . .
O5 O 0.6751(5) 0.8634(5) 0.4993(3) 0.0208(10) Uani 1.0 2 d . . .
O6 O 0.9930(5) 0.6483(5) 0.4220(3) 0.0219(10) Uani 1.0 2 d . . .
O7 O 0.8141(5) 0.5634(5) 0.4495(3) 0.0235(10) Uani 1.0 2 d . . .
O8 O 0.5244(5) 0.9866(4) 0.1916(3) 0.0195(10) Uani 1.0 2 d . . .
C1 C 0.8464(7) 1.1346(6) 0.2840(4) 0.0166(13) Uani 1.0 2 d . . .
C2 C 0.9478(7) 1.1972(7) 0.2744(5) 0.0229(14) Uani 1.0 2 d . . .
C3 C 0.9745(7) 1.2187(7) 0.3580(5) 0.0214(14) Uani 1.0 2 d . . .
C4 C 0.8994(7) 1.1844(6) 0.4457(5) 0.0209(14) Uani 1.0 2 d . . .
C5 C 0.7994(7) 1.1251(7) 0.4497(4) 0.0174(13) Uani 1.0 2 d . . .
C6 C 0.7718(7) 1.0954(6) 0.3692(4) 0.0178(13) Uani 1.0 2 d . . .
C7 C 0.6556(7) 1.0528(6) 0.3459(4) 0.0165(13) Uani 1.0 2 d . . .
C8 C 0.6466(7) 0.9086(6) 0.4008(4) 0.0176(13) Uani 1.0 2 d . . .
C9 C 0.7551(7) 0.7897(6) 0.3435(4) 0.0175(13) Uani 1.0 2 d . . .
C10 C 0.8333(7) 0.8653(6) 0.2625(4) 0.0170(13) Uani 1.0 2 d . . .
C11 C 0.7190(7) 1.0283(6) 0.2435(4) 0.0165(13) Uani 1.0 2 d . . .
C12 C 0.8668(8) 0.6613(7) 0.4088(4) 0.0204(14) Uani 1.0 2 d . . .
C13 C 1.1538(8) 1.3136(8) 0.2777(5) 0.0307(16) Uani 1.0 2 d . . .
C14 C 0.7260(9) 1.1396(8) 0.6125(5) 0.0298(16) Uani 1.0 2 d . . .
C15 C 0.8979(7) 0.8025(7) 0.1750(4) 0.0206(14) Uani 1.0 2 d . . .
C16 C 0.8599(8) 0.7004(7) 0.1544(5) 0.0231(15) Uani 1.0 2 d . . .
C17 C 0.9271(8) 0.6466(7) 0.0736(5) 0.0288(16) Uani 1.0 2 d . . .
C18 C 1.0271(8) 0.6933(7) 0.0122(5) 0.0280(16) Uani 1.0 2 d . . .
C19 C 1.0632(8) 0.7943(8) 0.0321(5) 0.0288(16) Uani 1.0 2 d . . .
C20 C 0.9999(8) 0.8488(7) 0.1127(5) 0.0259(15) Uani 1.0 2 d . . .
C21 C 0.5995(7) 1.0736(7) 0.1751(4) 0.0182(13) Uani 1.0 2 d . . .
C22 C 0.4183(7) 1.0479(7) 0.1220(4) 0.0192(14) Uani 1.0 2 d . . .
C23 C 0.4278(8) 1.1681(7) 0.0640(5) 0.0239(15) Uani 1.0 2 d . . .
C24 C 0.5456(8) 1.1860(7) 0.0994(5) 0.0238(15) Uani 1.0 2 d . . .
C25 C 0.5070(8) 0.4837(8) 0.2477(5) 0.0353(18) Uani 1.0 2 d . . .
H2 H 0.9954 1.2234 0.2148 0.0274 Uiso 1.0 2 calc R . .
H4 H 0.4814 1.1943 0.3950 0.0253 Uiso 1.0 2 calc R . .
H4A H 0.9183 1.2023 0.5016 0.0250 Uiso 1.0 2 calc R . .
H5 H 0.7607 0.8586 0.5067 0.0250 Uiso 1.0 2 calc R . .
H7 H 0.8810 0.4921 0.4838 0.0282 Uiso 1.0 2 calc R . .
H8 H 0.5397 0.9226 0.3958 0.0211 Uiso 1.0 2 calc R . .
H9 H 0.6920 0.7579 0.3159 0.0209 Uiso 1.0 2 calc R . .
H10 H 0.9231 0.8588 0.2909 0.0204 Uiso 1.0 2 calc R . .
H13A H 1.0870 1.4108 0.2430 0.0368 Uiso 1.0 2 calc R . .
H13B H 1.1805 1.2438 0.2381 0.0368 Uiso 1.0 2 calc R . .
H13C H 1.2474 1.3142 0.2928 0.0368 Uiso 1.0 2 calc R . .
H14A H 0.6804 1.2459 0.5983 0.0357 Uiso 1.0 2 calc R . .
H14B H 0.8334 1.1012 0.6274 0.0357 Uiso 1.0 2 calc R . .
H14C H 0.6699 1.1038 0.6672 0.0357 Uiso 1.0 2 calc R . .
H16 H 0.7896 0.6686 0.1950 0.0278 Uiso 1.0 2 calc R . .
H17 H 0.9038 0.5758 0.0602 0.0346 Uiso 1.0 2 calc R . .
H18 H 1.0705 0.6561 -0.0432 0.0337 Uiso 1.0 2 calc R . .
H19 H 1.1321 0.8268 -0.0098 0.0345 Uiso 1.0 2 calc R . .
H20 H 1.0258 0.9183 0.1258 0.0310 Uiso 1.0 2 calc R . .
H23 H 0.3685 1.2287 0.0104 0.0286 Uiso 1.0 2 calc R . .
H24 H 0.5784 1.2613 0.0746 0.0286 Uiso 1.0 2 calc R . .
H25 H 0.5260 0.3791 0.2669 0.0423 Uiso 1.0 2 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Br1 C22 1.836(9) yes . .
Cl31 C25 1.740(10) yes . .
Cl32 C25 1.766(8) yes . .
Cl33 C25 1.757(7) yes . .
O1 C1 1.372(9) yes . .
O1 C11 1.449(9) yes . .
O2 C3 1.371(11) yes . .
O2 C13 1.428(9) yes . .
O3 C5 1.374(7) yes . .
O3 C14 1.433(10) yes . .
O4 C7 1.431(6) yes . .
O5 C8 1.419(7) yes . .
O6 C12 1.221(10) yes . .
O7 C12 1.317(9) yes . .
O8 C21 1.369(10) yes . .
O8 C22 1.383(8) yes . .
C1 C2 1.392(12) yes . .
C1 C6 1.394(9) yes . .
C2 C3 1.386(11) yes . .
C3 C4 1.410(9) yes . .
C4 C5 1.368(12) yes . .
C5 C6 1.393(10) yes . .
C6 C7 1.512(12) yes . .
C7 C8 1.551(9) yes . .
C7 C11 1.566(9) yes . .
C8 C9 1.579(8) yes . .
C9 C10 1.536(9) yes . .
C9 C12 1.500(7) yes . .
C10 C11 1.552(7) yes . .
C10 C15 1.516(9) yes . .
C11 C21 1.488(10) yes . .
C15 C16 1.406(12) yes . .
C15 C20 1.400(10) yes . .
C16 C17 1.388(10) yes . .
C17 C18 1.381(11) yes . .
C18 C19 1.377(13) yes . .
C19 C20 1.384(10) yes . .
C21 C24 1.350(8) yes . .
C22 C23 1.354(10) yes . .
C23 C24 1.441(12) yes . .
O4 H4 0.840 no . .
O5 H5 0.840 no . .
O7 H7 0.840 no . .
C2 H2 0.950 no . .
C4 H4A 0.950 no . .
C8 H8 1.000 no . .
C9 H9 1.000 no . .
C10 H10 1.000 no . .
C13 H13A 0.980 no . .
C13 H13B 0.980 no . .
C13 H13C 0.980 no . .
C14 H14A 0.980 no . .
C14 H14B 0.980 no . .
C14 H14C 0.980 no . .
C16 H16 0.950 no . .
C17 H17 0.950 no . .
C18 H18 0.950 no . .
C19 H19 0.950 no . .
C20 H20 0.950 no . .
C23 H23 0.950 no . .
C24 H24 0.950 no . .
C25 H25 1.000 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 O1 C11 105.5(5) yes . . .
C3 O2 C13 117.4(6) yes . . .
C5 O3 C14 117.1(7) yes . . .
C21 O8 C22 105.8(5) yes . . .
O1 C1 C2 121.1(6) yes . . .
O1 C1 C6 113.7(7) yes . . .
C2 C1 C6 125.0(7) yes . . .
C1 C2 C3 115.3(6) yes . . .
O2 C3 C2 124.0(6) yes . . .
O2 C3 C4 113.9(7) yes . . .
C2 C3 C4 122.1(8) yes . . .
C3 C4 C5 119.4(7) yes . . .
O3 C5 C4 123.4(7) yes . . .
O3 C5 C6 115.2(7) yes . . .
C4 C5 C6 121.4(6) yes . . .
C1 C6 C5 116.7(7) yes . . .
C1 C6 C7 107.9(6) yes . . .
C5 C6 C7 134.4(6) yes . . .
O4 C7 C6 109.9(6) yes . . .
O4 C7 C8 110.7(5) yes . . .
O4 C7 C11 110.3(5) yes . . .
C6 C7 C8 121.1(5) yes . . .
C6 C7 C11 99.3(5) yes . . .
C8 C7 C11 104.3(6) yes . . .
O5 C8 C7 116.8(7) yes . . .
O5 C8 C9 112.8(4) yes . . .
C7 C8 C9 106.7(5) yes . . .
C8 C9 C10 105.7(5) yes . . .
C8 C9 C12 109.8(5) yes . . .
C10 C9 C12 112.9(5) yes . . .
C9 C10 C11 104.7(5) yes . . .
C9 C10 C15 118.6(6) yes . . .
C11 C10 C15 115.8(5) yes . . .
O1 C11 C7 106.5(6) yes . . .
O1 C11 C10 109.8(5) yes . . .
O1 C11 C21 106.8(5) yes . . .
C7 C11 C10 103.2(4) yes . . .
C7 C11 C21 114.8(5) yes . . .
C10 C11 C21 115.4(7) yes . . .
O6 C12 O7 123.8(5) yes . . .
O6 C12 C9 123.8(7) yes . . .
O7 C12 C9 112.3(7) yes . . .
C10 C15 C16 122.8(6) yes . . .
C10 C15 C20 118.1(7) yes . . .
C16 C15 C20 119.1(6) yes . . .
C15 C16 C17 118.8(7) yes . . .
C16 C17 C18 121.8(8) yes . . .
C17 C18 C19 119.3(7) yes . . .
C18 C19 C20 120.4(7) yes . . .
C15 C20 C19 120.6(8) yes . . .
O8 C21 C11 115.0(5) yes . . .
O8 C21 C24 111.5(7) yes . . .
C11 C21 C24 133.5(8) yes . . .
Br1 C22 O8 116.4(5) yes . . .
Br1 C22 C23 133.3(6) yes . . .
O8 C22 C23 110.3(7) yes . . .
C22 C23 C24 106.7(6) yes . . .
C21 C24 C23 105.7(7) yes . . .
Cl31 C25 Cl32 110.7(5) yes . . .
Cl31 C25 Cl33 111.2(5) yes . . .
Cl32 C25 Cl33 111.2(4) yes . . .
C7 O4 H4 109.472 no . . .
C8 O5 H5 109.471 no . . .
C12 O7 H7 109.475 no . . .
C1 C2 H2 122.344 no . . .
C3 C2 H2 122.343 no . . .
C3 C4 H4A 120.277 no . . .
C5 C4 H4A 120.282 no . . .
O5 C8 H8 106.658 no . . .
C7 C8 H8 106.655 no . . .
C9 C8 H8 106.653 no . . .
C8 C9 H9 109.411 no . . .
C10 C9 H9 109.414 no . . .
C12 C9 H9 109.410 no . . .
C9 C10 H10 105.519 no . . .
C11 C10 H10 105.516 no . . .
C15 C10 H10 105.525 no . . .
O2 C13 H13A 109.471 no . . .
O2 C13 H13B 109.463 no . . .
O2 C13 H13C 109.479 no . . .
H13A C13 H13B 109.461 no . . .
H13A C13 H13C 109.478 no . . .
H13B C13 H13C 109.475 no . . .
O3 C14 H14A 109.476 no . . .
O3 C14 H14B 109.474 no . . .
O3 C14 H14C 109.474 no . . .
H14A C14 H14B 109.471 no . . .
H14A C14 H14C 109.467 no . . .
H14B C14 H14C 109.465 no . . .
C15 C16 H16 120.627 no . . .
C17 C16 H16 120.621 no . . .
C16 C17 H17 119.089 no . . .
C18 C17 H17 119.083 no . . .
C17 C18 H18 120.341 no . . .
C19 C18 H18 120.340 no . . .
C18 C19 H19 119.792 no . . .
C20 C19 H19 119.786 no . . .
C15 C20 H20 119.703 no . . .
C19 C20 H20 119.713 no . . .
C22 C23 H23 126.659 no . . .
C24 C23 H23 126.655 no . . .
C21 C24 H24 127.152 no . . .
C23 C24 H24 127.147 no . . .
Cl31 C25 H25 107.859 no . . .
Cl32 C25 H25 107.863 no . . .
Cl33 C25 H25 107.862 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 O1 C11 C7 25.3(5) no . . . .
C1 O1 C11 C10 -85.8(5) no . . . .
C1 O1 C11 C21 148.4(4) no . . . .
C11 O1 C1 C2 170.6(4) no . . . .
C11 O1 C1 C6 -14.4(5) no . . . .
C13 O2 C3 C2 2.2(7) no . . . .
C13 O2 C3 C4 -178.5(4) no . . . .
C14 O3 C5 C4 7.6(7) no . . . .
C14 O3 C5 C6 -171.5(4) no . . . .
C21 O8 C22 Br1 178.4(4) no . . . .
C21 O8 C22 C23 0.5(6) no . . . .
C22 O8 C21 C11 179.1(4) no . . . .
C22 O8 C21 C24 0.2(6) no . . . .
O1 C1 C2 C3 175.1(4) no . . . .
O1 C1 C6 C5 -173.1(4) no . . . .
O1 C1 C6 C7 -3.1(6) no . . . .
C2 C1 C6 C5 1.6(8) no . . . .
C2 C1 C6 C7 171.7(5) no . . . .
C6 C1 C2 C3 0.7(8) no . . . .
C1 C2 C3 O2 176.9(5) no . . . .
C1 C2 C3 C4 -2.3(7) no . . . .
O2 C3 C4 C5 -177.9(4) no . . . .
C2 C3 C4 C5 1.4(8) no . . . .
C3 C4 C5 O3 -177.9(4) no . . . .
C3 C4 C5 C6 1.1(7) no . . . .
O3 C5 C6 C1 176.6(4) no . . . .
O3 C5 C6 C7 9.9(8) no . . . .
C4 C5 C6 C1 -2.6(7) no . . . .
C4 C5 C6 C7 -169.3(5) no . . . .
C1 C6 C7 O4 -98.3(5) no . . . .
C1 C6 C7 C8 130.4(5) no . . . .
C1 C6 C7 C11 17.4(5) no . . . .
C5 C6 C7 O4 69.2(7) no . . . .
C5 C6 C7 C8 -62.0(8) no . . . .
C5 C6 C7 C11 -175.1(6) no . . . .
O4 C7 C8 O5 -94.8(6) no . . . .
O4 C7 C8 C9 138.1(5) no . . . .
O4 C7 C11 O1 89.6(6) no . . . .
O4 C7 C11 C10 -154.8(5) no . . . .
O4 C7 C11 C21 -28.3(8) no . . . .
C6 C7 C8 O5 36.1(7) no . . . .
C6 C7 C8 C9 -91.1(6) no . . . .
C6 C7 C11 O1 -25.8(5) no . . . .
C6 C7 C11 C10 89.8(5) no . . . .
C6 C7 C11 C21 -143.7(5) no . . . .
C8 C7 C11 O1 -151.4(5) no . . . .
C8 C7 C11 C10 -35.8(6) no . . . .
C8 C7 C11 C21 90.6(6) no . . . .
C11 C7 C8 O5 146.5(5) no . . . .
C11 C7 C8 C9 19.4(6) no . . . .
O5 C8 C9 C10 -125.0(6) no . . . .
O5 C8 C9 C12 -2.9(8) no . . . .
C7 C8 C9 C10 4.5(7) no . . . .
C7 C8 C9 C12 126.7(6) no . . . .
C8 C9 C10 C11 -27.0(7) no . . . .
C8 C9 C10 C15 -157.9(5) no . . . .
C8 C9 C12 O6 -90.8(7) no . . . .
C8 C9 C12 O7 89.8(7) no . . . .
C10 C9 C12 O6 26.9(9) no . . . .
C10 C9 C12 O7 -152.4(6) no . . . .
C12 C9 C10 C11 -147.1(6) no . . . .
C12 C9 C10 C15 81.9(8) no . . . .
C9 C10 C11 O1 152.3(5) no . . . .
C9 C10 C11 C7 39.1(7) no . . . .
C9 C10 C11 C21 -87.0(6) no . . . .
C9 C10 C15 C16 15.1(8) no . . . .
C9 C10 C15 C20 -164.8(5) no . . . .
C11 C10 C15 C16 -110.8(6) no . . . .
C11 C10 C15 C20 69.3(8) no . . . .
C15 C10 C11 O1 -75.1(8) no . . . .
C15 C10 C11 C7 171.7(6) no . . . .
C15 C10 C11 C21 45.6(8) no . . . .
O1 C11 C21 O8 170.8(4) no . . . .
O1 C11 C21 C24 -10.6(8) no . . . .
C7 C11 C21 O8 -71.4(7) no . . . .
C7 C11 C21 C24 107.2(7) no . . . .
C10 C11 C21 O8 48.4(7) no . . . .
C10 C11 C21 C24 -133.0(7) no . . . .
C10 C15 C16 C17 -178.7(4) no . . . .
C10 C15 C20 C19 179.6(4) no . . . .
C16 C15 C20 C19 -0.4(8) no . . . .
C20 C15 C16 C17 1.2(8) no . . . .
C15 C16 C17 C18 -1.5(8) no . . . .
C16 C17 C18 C19 1.0(9) no . . . .
C17 C18 C19 C20 -0.1(9) no . . . .
C18 C19 C20 C15 -0.2(9) no . . . .
O8 C21 C24 C23 -0.8(7) no . . . .
C11 C21 C24 C23 -179.4(6) no . . . .
Br1 C22 C23 C24 -178.4(4) no . . . .
O8 C22 C23 C24 -0.9(7) no . . . .
C22 C23 C24 C21 1.0(7) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 O4 3.136(6) no . .
O1 C5 3.583(8) no . .
O1 C15 3.172(9) no . .
O1 C20 3.163(8) no . .
O1 C24 2.872(9) no . .
O2 C5 3.596(10) no . .
O3 O4 3.418(7) no . .
O3 O5 2.805(8) no . .
O3 C7 3.048(9) no . .
O3 C8 3.408(10) no . .
O4 O5 3.310(5) no . .
O4 O8 3.263(7) no . .
O4 C1 3.159(8) no . .
O4 C5 3.271(9) no . .
O4 C21 2.768(8) no . .
O4 C24 3.470(8) no . .
O5 O6 3.165(6) no . .
O5 O7 3.086(7) no . .
O5 C5 3.363(10) no . .
O5 C6 3.078(8) no . .
O5 C10 3.549(7) no . .
O5 C12 2.640(7) no . .
O6 C8 3.264(7) no . .
O6 C10 2.862(6) no . .
O7 C8 3.180(7) no . .
O8 C7 3.140(10) no . .
O8 C8 3.223(8) no . .
O8 C9 3.042(7) no . .
O8 C10 2.944(8) no . .
O8 C15 3.283(7) no . .
O8 C16 3.409(7) no . .
C1 C4 2.733(11) no . .
C1 C10 3.013(11) no . .
C1 C21 3.468(12) no . .
C2 C5 2.820(9) no . .
C2 C11 3.576(12) no . .
C2 C13 2.806(13) no . .
C3 C6 2.786(12) no . .
C4 C14 2.787(9) no . .
C5 C8 3.512(12) no . .
C6 C9 3.435(11) no . .
C6 C10 3.030(10) no . .
C8 C21 3.279(8) no . .
C9 C16 3.035(9) no . .
C9 C21 3.235(7) no . .
C11 C20 3.223(8) no . .
C11 C22 3.581(11) no . .
C12 C15 3.356(8) no . .
C15 C18 2.793(9) no . .
C15 C21 3.037(8) no . .
C16 C19 2.788(11) no . .
C17 C20 2.754(13) no . .
Br1 C23 3.549(6) no . 2_675
Cl31 O7 3.282(6) no . .
Cl33 O6 3.565(5) no . 1_455
Cl33 C20 3.498(6) no . 1_455
O1 C19 3.539(8) no . 2_775
O2 O3 3.480(6) no . 2_776
O2 O5 2.982(7) no . 2_776
O2 O6 3.342(7) no . 2_776
O2 O7 3.399(6) no . 1_565
O3 O2 3.480(6) no . 2_776
O3 C3 3.506(7) no . 2_776
O3 C4 3.568(7) no . 2_776
O3 C8 3.542(9) no . 2_676
O4 O5 2.732(6) no . 2_676
O4 C13 3.271(9) no . 1_455
O4 C25 3.208(10) no . 1_565
O5 O2 2.982(7) no . 2_776
O5 O4 2.732(6) no . 2_676
O5 O5 3.346(5) no . 2_676
O5 C7 3.533(7) no . 2_676
O5 C8 3.384(7) no . 2_676
O5 C13 3.545(8) no . 2_776
O6 Cl33 3.565(5) no . 1_655
O6 O2 3.342(7) no . 2_776
O6 O6 3.295(6) no . 2_766
O6 O7 2.676(5) no . 2_766
O6 C4 3.493(10) no . 2_776
O6 C12 3.370(7) no . 2_766
O7 Cl31 3.282(6) no . .
O7 O2 3.399(6) no . 1_545
O7 O6 2.676(5) no . 2_766
O7 C12 3.527(8) no . 2_766
C3 O3 3.506(7) no . 2_776
C3 C14 3.561(8) no . 2_776
C4 O3 3.568(7) no . 2_776
C4 O6 3.493(10) no . 2_776
C4 C4 3.513(8) no . 2_776
C4 C5 3.436(7) no . 2_776
C5 C4 3.436(7) no . 2_776
C7 O5 3.533(7) no . 2_676
C8 O3 3.542(9) no . 2_676
C8 O5 3.384(7) no . 2_676
C12 O6 3.370(7) no . 2_766
C12 O7 3.527(8) no . 2_766
C13 O4 3.271(9) no . 1_655
C13 O5 3.545(8) no . 2_776
C14 C3 3.561(8) no . 2_776
C19 O1 3.539(8) no . 2_775
C20 Cl33 3.498(6) no . 1_655
C23 Br1 3.549(6) no . 2_675
C25 O4 3.208(10) no . 1_545
Br1 H23 3.2311 no . .
O1 H2 2.6358 no . .
O1 H10 2.4793 no . .
O1 H20 2.6419 no . .
O1 H24 2.7482 no . .
O2 H2 2.6824 no . .
O2 H4A 2.4821 no . .
O3 H4 2.9295 no . .
O3 H4A 2.6238 no . .
O3 H5 2.4360 no . .
O4 H8 2.4223 no . .
O5 H4 3.1990 no . .
O5 H7 3.5743 no . .
O5 H9 3.1282 no . .
O5 H10 3.5634 no . .
O6 H5 2.7723 no . .
O6 H7 2.2881 no . .
O6 H9 3.1419 no . .
O6 H10 2.4128 no . .
O7 H5 3.2492 no . .
O7 H8 3.4869 no . .
O7 H9 2.4143 no . .
O7 H16 3.5928 no . .
O8 H8 2.8877 no . .
O8 H9 2.6168 no . .
O8 H16 3.1868 no . .
O8 H23 3.1620 no . .
O8 H24 3.1639 no . .
C1 H4 3.5226 no . .
C1 H10 2.6436 no . .
C1 H20 3.4100 no . .
C2 H4A 3.2976 no . .
C2 H13A 3.0277 no . .
C2 H13B 2.4848 no . .
C3 H13A 2.7743 no . .
C3 H13B 2.5030 no . .
C3 H13C 3.1811 no . .
C4 H2 3.3134 no . .
C4 H14A 2.8207 no . .
C4 H14B 2.6280 no . .
C5 H4 3.0502 no . .
C5 H5 2.8902 no . .
C5 H14A 2.6568 no . .
C5 H14B 2.6018 no . .
C5 H14C 3.2088 no . .
C6 H2 3.3269 no . .
C6 H4 2.5498 no . .
C6 H4A 3.2641 no . .
C6 H5 2.7815 no . .
C6 H8 3.4211 no . .
C6 H10 2.7290 no . .
C7 H5 2.6544 no . .
C7 H9 3.1235 no . .
C7 H10 2.6624 no . .
C8 H4 2.6976 no . .
C8 H10 2.8146 no . .
C9 H5 2.6939 no . .
C9 H7 3.0728 no . .
C9 H16 2.7131 no . .
C10 H5 3.5097 no . .
C10 H8 3.1068 no . .
C10 H16 2.7484 no . .
C10 H20 2.6360 no . .
C11 H4 3.1871 no . .
C11 H8 2.8969 no . .
C11 H9 2.8814 no . .
C11 H20 3.0956 no . .
C11 H24 2.9654 no . .
C12 H5 2.5858 no . .
C12 H8 3.1438 no . .
C12 H10 2.5267 no . .
C12 H16 3.3063 no . .
C13 H2 2.5371 no . .
C14 H4A 2.4766 no . .
C14 H5 3.5766 no . .
C15 H9 2.7337 no . .
C15 H17 3.2610 no . .
C15 H19 3.2733 no . .
C16 H9 2.6925 no . .
C16 H10 3.2173 no . .
C16 H18 3.2740 no . .
C16 H20 3.2775 no . .
C17 H19 3.2393 no . .
C18 H16 3.2747 no . .
C18 H20 3.2499 no . .
C19 H17 3.2343 no . .
C20 H10 2.6077 no . .
C20 H16 3.2820 no . .
C20 H18 3.2546 no . .
C21 H8 3.2693 no . .
C21 H9 3.2150 no . .
C21 H10 3.3526 no . .
C21 H23 3.1443 no . .
C22 H24 3.1615 no . .
H2 H13A 2.6598 no . .
H2 H13B 2.0091 no . .
H2 H13C 3.4580 no . .
H4 H5 3.5091 no . .
H4 H8 2.6652 no . .
H4A H14A 2.4365 no . .
H4A H14B 2.1053 no . .
H4A H14C 3.4359 no . .
H5 H8 2.6452 no . .
H5 H9 3.5009 no . .
H5 H10 3.2880 no . .
H7 H9 3.2225 no . .
H8 H9 2.1983 no . .
H9 H10 2.8401 no . .
H9 H16 2.1150 no . .
H10 H16 3.4984 no . .
H10 H20 2.4838 no . .
H16 H17 2.3337 no . .
H17 H18 2.3229 no . .
H18 H19 2.3289 no . .
H19 H20 2.3264 no . .
H23 H24 2.5821 no . .
Br1 H2 3.4746 no . 1_455
Br1 H13B 3.5606 no . 1_455
Br1 H14C 2.9954 no . 2_676
Br1 H19 3.5652 no . 1_455
Br1 H20 2.8663 no . 1_455
Br1 H23 3.5085 no . 2_675
Cl31 H9 3.0717 no . .
Cl31 H14A 3.0343 no . 2_676
Cl31 H16 3.1434 no . .
Cl32 H16 3.4179 no . .
Cl32 H17 3.3707 no . .
Cl32 H18 3.2416 no . 2_765
Cl32 H23 3.0763 no . 2_675
Cl32 H24 3.0682 no . 1_545
Cl32 H24 3.3986 no . 2_675
Cl33 H13A 3.4804 no . 1_445
Cl33 H13C 3.1042 no . 1_445
Cl33 H14A 3.2076 no . 2_676
Cl33 H20 3.5537 no . 1_455
O1 H18 3.3984 no . 2_775
O1 H19 2.7904 no . 2_775
O1 H25 3.0953 no . 1_565
O2 H5 2.3718 no . 2_776
O2 H7 3.0403 no . 1_565
O3 H4A 3.5936 no . 2_776
O3 H8 2.6236 no . 2_676
O4 H5 3.2125 no . 2_676
O4 H13B 3.4429 no . 1_455
O4 H13C 2.4080 no . 1_455
O4 H25 2.2413 no . 1_565
O5 H4 2.1559 no . 2_676
O5 H8 2.9087 no . 2_676
O5 H13C 3.1129 no . 2_776
O6 H4A 2.6497 no . 2_776
O6 H7 1.8468 no . 2_766
O7 H4A 3.3738 no . 1_545
O7 H7 3.0437 no . 2_766
O8 H13B 3.3496 no . 1_455
O8 H14C 2.8361 no . 2_676
C1 H14B 3.2012 no . 2_776
C1 H25 3.0321 no . 1_565
C2 H14B 3.0099 no . 2_776
C2 H18 3.3062 no . 2_775
C3 H5 3.1919 no . 2_776
C3 H7 3.5464 no . 1_565
C3 H14B 3.0090 no . 2_776
C4 H4A 3.5612 no . 2_776
C4 H5 3.3124 no . 2_776
C4 H7 3.3737 no . 1_565
C4 H14B 3.2951 no . 2_776
C5 H4A 3.2910 no . 2_776
C5 H14B 3.5105 no . 2_776
C6 H4A 3.5662 no . 2_776
C6 H14B 3.4679 no . 2_776
C6 H25 3.0432 no . 1_565
C7 H25 3.0374 no . 1_565
C8 H4 3.1423 no . 2_676
C8 H14C 3.4699 no . 2_676
C11 H25 3.4128 no . 1_565
C12 H4A 3.5908 no . 2_776
C12 H7 2.7318 no . 2_766
C13 H4 3.4335 no . 1_655
C13 H5 3.2091 no . 2_776
C14 H8 2.9816 no . 2_676
C16 H13A 2.9415 no . 1_545
C16 H23 3.2604 no . 2_675
C17 H13A 3.0297 no . 1_545
C17 H17 3.1732 no . 2_765
C17 H18 3.3437 no . 2_765
C17 H23 2.9090 no . 2_675
C18 H2 3.2086 no . 2_775
C18 H17 3.0626 no . 2_765
C19 H19 3.5270 no . 2_775
C19 H20 3.1242 no . 2_775
C19 H24 3.4520 no . 2_775
C20 H19 3.0881 no . 2_775
C21 H19 3.5844 no . 2_775
C21 H25 3.5705 no . 1_565
C22 H13B 2.9802 no . 1_455
C22 H14C 3.2350 no . 2_676
C22 H23 3.5997 no . 2_675
C23 H13B 3.2123 no . 1_455
C23 H17 3.5356 no . 2_675
C24 H19 3.1675 no . 2_775
C24 H25 3.5290 no . 1_565
C25 H4 3.3118 no . 1_545
H2 Br1 3.4746 no . 1_655
H2 C18 3.2086 no . 2_775
H2 H14B 3.4166 no . 2_776
H2 H17 3.5852 no . 1_565
H2 H18 2.5239 no . 2_775
H4 O5 2.1559 no . 2_676
H4 C8 3.1423 no . 2_676
H4 C13 3.4335 no . 1_455
H4 C25 3.3118 no . 1_565
H4 H5 2.7603 no . 2_676
H4 H8 2.9780 no . 2_676
H4 H13C 2.5605 no . 1_455
H4 H25 2.4507 no . 1_565
H4A O3 3.5936 no . 2_776
H4A O6 2.6497 no . 2_776
H4A O7 3.3738 no . 1_565
H4A C4 3.5612 no . 2_776
H4A C5 3.2910 no . 2_776
H4A C6 3.5662 no . 2_776
H4A C12 3.5908 no . 2_776
H4A H5 2.8963 no . 2_776
H4A H7 2.8627 no . 1_565
H4A H10 3.4052 no . 2_776
H5 O2 2.3718 no . 2_776
H5 O4 3.2125 no . 2_676
H5 C3 3.1919 no . 2_776
H5 C4 3.3124 no . 2_776
H5 C13 3.2091 no . 2_776
H5 H4 2.7603 no . 2_676
H5 H4A 2.8963 no . 2_776
H5 H8 3.2159 no . 2_676
H5 H13C 3.0090 no . 2_776
H7 O2 3.0403 no . 1_545
H7 O6 1.8468 no . 2_766
H7 O7 3.0437 no . 2_766
H7 C3 3.5464 no . 1_545
H7 C4 3.3737 no . 1_545
H7 C12 2.7318 no . 2_766
H7 H4A 2.8627 no . 1_545
H7 H7 2.5367 no . 2_766
H8 O3 2.6236 no . 2_676
H8 O5 2.9087 no . 2_676
H8 C14 2.9816 no . 2_676
H8 H4 2.9780 no . 2_676
H8 H5 3.2159 no . 2_676
H8 H14A 3.3363 no . 2_676
H8 H14C 2.5321 no . 2_676
H9 Cl31 3.0717 no . .
H9 H14C 3.1609 no . 2_676
H10 H4A 3.4052 no . 2_776
H10 H14B 3.0660 no . 2_776
H13A Cl33 3.4804 no . 1_665
H13A C16 2.9415 no . 1_565
H13A C17 3.0297 no . 1_565
H13A H16 2.9815 no . 1_565
H13A H17 3.0991 no . 1_565
H13B Br1 3.5606 no . 1_655
H13B O4 3.4429 no . 1_655
H13B O8 3.3496 no . 1_655
H13B C22 2.9802 no . 1_655
H13B C23 3.2123 no . 1_655
H13B H14C 3.2590 no . 2_776
H13B H23 3.5349 no . 1_655
H13C Cl33 3.1042 no . 1_665
H13C O4 2.4080 no . 1_655
H13C O5 3.1129 no . 2_776
H13C H4 2.5605 no . 1_655
H13C H5 3.0090 no . 2_776
H13C H25 3.0407 no . 1_665
H14A Cl31 3.0343 no . 2_676
H14A Cl33 3.2076 no . 2_676
H14A H8 3.3363 no . 2_676
H14B C1 3.2012 no . 2_776
H14B C2 3.0099 no . 2_776
H14B C3 3.0090 no . 2_776
H14B C4 3.2951 no . 2_776
H14B C5 3.5105 no . 2_776
H14B C6 3.4679 no . 2_776
H14B H2 3.4166 no . 2_776
H14B H10 3.0660 no . 2_776
H14C Br1 2.9954 no . 2_676
H14C O8 2.8361 no . 2_676
H14C C8 3.4699 no . 2_676
H14C C22 3.2350 no . 2_676
H14C H8 2.5321 no . 2_676
H14C H9 3.1609 no . 2_676
H14C H13B 3.2590 no . 2_776
H16 Cl31 3.1434 no . .
H16 Cl32 3.4179 no . .
H16 H13A 2.9815 no . 1_545
H16 H23 3.2881 no . 2_675
H17 Cl32 3.3707 no . .
H17 C17 3.1732 no . 2_765
H17 C18 3.0626 no . 2_765
H17 C23 3.5356 no . 2_675
H17 H2 3.5852 no . 1_545
H17 H13A 3.0991 no . 1_545
H17 H17 2.6385 no . 2_765
H17 H18 2.4311 no . 2_765
H17 H23 2.6863 no . 2_675
H18 Cl32 3.2416 no . 2_765
H18 O1 3.3984 no . 2_775
H18 C2 3.3062 no . 2_775
H18 C17 3.3437 no . 2_765
H18 H2 2.5239 no . 2_775
H18 H17 2.4311 no . 2_765
H19 Br1 3.5652 no . 1_655
H19 O1 2.7904 no . 2_775
H19 C19 3.5270 no . 2_775
H19 C20 3.0881 no . 2_775
H19 C21 3.5844 no . 2_775
H19 C24 3.1675 no . 2_775
H19 H19 3.4667 no . 2_775
H19 H20 2.6729 no . 2_775
H19 H24 2.6487 no . 2_775
H20 Br1 2.8663 no . 1_655
H20 Cl33 3.5537 no . 1_655
H20 C19 3.1242 no . 2_775
H20 H19 2.6729 no . 2_775
H23 Br1 3.5085 no . 2_675
H23 Cl32 3.0763 no . 2_675
H23 C16 3.2604 no . 2_675
H23 C17 2.9090 no . 2_675
H23 C22 3.5997 no . 2_675
H23 H13B 3.5349 no . 1_455
H23 H16 3.2881 no . 2_675
H23 H17 2.6863 no . 2_675
H24 Cl32 3.0682 no . 1_565
H24 Cl32 3.3986 no . 2_675
H24 C19 3.4520 no . 2_775
H24 H19 2.6487 no . 2_775
H24 H25 3.2554 no . 1_565
H25 O1 3.0953 no . 1_545
H25 O4 2.2413 no . 1_545
H25 C1 3.0321 no . 1_545
H25 C6 3.0432 no . 1_545
H25 C7 3.0374 no . 1_545
H25 C11 3.4128 no . 1_545
H25 C21 3.5705 no . 1_545
H25 C24 3.5290 no . 1_545
H25 H4 2.4507 no . 1_545
H25 H13C 3.0407 no . 1_445
H25 H24 3.2554 no . 1_545

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O4 H4 O5 . . 2_676 2.732(6) 0.840 2.156 125.6 no
O5 H5 O2 . . 2_776 2.982(7) 0.840 2.372 129.9 no
O5 H5 O3 . . . 2.805(8) 0.840 2.436 107.5 no
O7 H7 O6 . . 2_766 2.676(5) 0.840 1.847 169.1 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
