# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Nepogodiev, Sergey'
'Fais, Margherita'
'Hughes, David'
'Field, Robert'

_publ_contact_author_name        'Nepogodiev, Sergey'
_publ_contact_author_email       sergey.nepogodiev@bbsrc.ac.uk

_publ_section_title              
;
Synthesis of apiose-containing oligosaccharide fragments
of the plant cell wall: fragments of rhamnogalacturonan-II
side chains A and B, and apiogalacturonan
;

# Attachment '- sn1aa.cif'

#
# To accompany the MS submitted to Org. Biomol. Chem.:
#
# Synthesis of apiose-containing oligosaccharide fragments of the plant...
#
# by S.A. Nepogodiev, M. Fais, D.L. Hughes and R.A. Field
#

data_sergeyn1
_database_code_depnum_ccdc_archive 'CCDC 821796'
#TrackingRef '- sn1aa.cif'

_audit_creation_method           'SHELXL-97 and CrysAlis RED'
_chemical_name_systematic        
;
?
;
_chemical_name_common            'Compound 41'
_chemical_melting_point          ?
_chemical_formula_structural     'Rha-Api-GalA derivative'
_chemical_formula_moiety         'C32 H40 O17, C H2 Cl2'
_chemical_formula_sum            'C33 H42 Cl2 O17'
_chemical_formula_weight         781.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P212121

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                   11.2799(6)
_cell_length_b                   15.1788(9)
_cell_length_c                   21.4815(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3678.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(1)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1640
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.995
_exptl_absorpt_correction_T_max  1.005
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28c4 beta
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      140(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur 3/CCD'
_diffrn_measurement_method       'Thin slice \f and \w scans'
_diffrn_detector_area_resol_mean 16.0050

_diffrn_reflns_number            49119
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.75
_diffrn_reflns_theta_max         27.50
_reflns_number_total             8410
_reflns_number_gt                7002
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.28c4 beta
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28c4 beta
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28c4 beta
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976 and Farrugia, 1997)'
_computing_publication_material  
'SHELXL-97 (Sheldrick, 2008) and WINGX (Farrugia, 1999)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0556P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(5)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         8410
_refine_ls_number_parameters     470
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0894
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.79620(16) 0.36811(12) 0.60142(9) 0.0214(4) Uani 1 1 d . . .
H1A H 0.7990 0.4309 0.5909 0.026 Uiso 1 1 calc R . .
O1A O 0.67726(11) 0.34408(8) 0.61388(6) 0.0205(3) Uani 1 1 d . . .
C2A C 0.83360(16) 0.31507(13) 0.54518(9) 0.0215(4) Uani 1 1 d . . .
H2A H 0.9114 0.3344 0.5302 0.026 Uiso 1 1 calc R . .
O2A O 0.74623(12) 0.32308(9) 0.49707(7) 0.0277(3) Uani 1 1 d . . .
C21A C 0.68646(17) 0.24750(16) 0.49125(9) 0.0287(5) Uani 1 1 d . . .
O22A O 0.60308(13) 0.23748(13) 0.45780(7) 0.0430(4) Uani 1 1 d . . .
C3A C 0.83435(16) 0.21530(13) 0.55960(9) 0.0200(4) Uani 1 1 d . . .
H3A H 0.9058 0.1881 0.5421 0.024 Uiso 1 1 calc R . .
O3A O 0.73108(12) 0.18345(10) 0.52732(7) 0.0267(3) Uani 1 1 d . . .
C4A C 0.82751(16) 0.19693(12) 0.62891(9) 0.0191(4) Uani 1 1 d . . .
H4A H 0.7453 0.2007 0.6434 0.023 Uiso 1 1 calc R . .
O4A O 0.87470(11) 0.11002(9) 0.63998(6) 0.0228(3) Uani 1 1 d . . .
C41A C 0.80623(16) 0.05302(13) 0.67190(9) 0.0230(4) Uani 1 1 d . . .
O41A O 0.70827(13) 0.06990(10) 0.68992(8) 0.0388(4) Uani 1 1 d . . .
C42A C 0.8684(2) -0.03299(14) 0.68191(11) 0.0310(5) Uani 1 1 d . . .
H42A H 0.8316 -0.0640 0.7157 0.047 Uiso 1 1 calc R . .
H42B H 0.9502 -0.0223 0.6917 0.047 Uiso 1 1 calc R . .
H42C H 0.8633 -0.0679 0.6447 0.047 Uiso 1 1 calc R . .
C5A C 0.90543(16) 0.26265(13) 0.66395(9) 0.0214(4) Uani 1 1 d . . .
H5A H 0.9879 0.2544 0.6509 0.026 Uiso 1 1 calc R . .
O5A O 0.87124(12) 0.35262(9) 0.65154(7) 0.0255(3) Uani 1 1 d . . .
C6A C 0.8980(2) 0.25094(16) 0.73355(10) 0.0367(5) Uani 1 1 d . . .
H6A1 H 0.9484 0.2933 0.7536 0.055 Uiso 1 1 calc R . .
H6A2 H 0.9233 0.1925 0.7444 0.055 Uiso 1 1 calc R . .
H6A3 H 0.8177 0.2596 0.7469 0.055 Uiso 1 1 calc R . .
C1B C 0.32355(17) 0.43145(12) 0.60298(8) 0.0199(4) Uani 1 1 d . . .
H1B H 0.2542 0.4105 0.5798 0.024 Uiso 1 1 calc R . .
O1B O 0.36479(12) 0.51151(8) 0.57915(6) 0.0214(3) Uani 1 1 d . . .
C2B C 0.42733(16) 0.36850(12) 0.59596(9) 0.0195(4) Uani 1 1 d . . .
H2B H 0.4798 0.3848 0.5615 0.023 Uiso 1 1 calc R . .
O2B O 0.38499(12) 0.28065(8) 0.59079(6) 0.0218(3) Uani 1 1 d . . .
C20B C 0.44849(16) 0.22809(12) 0.63397(9) 0.0198(4) Uani 1 1 d . . .
H20B H 0.5209 0.2050 0.6147 0.024 Uiso 1 1 calc R . .
C21B C 0.37170(16) 0.15315(13) 0.65668(9) 0.0210(4) Uani 1 1 d . . .
C22B C 0.25373(18) 0.16799(15) 0.67194(11) 0.0333(5) Uani 1 1 d . . .
H22B H 0.2214 0.2241 0.6680 0.040 Uiso 1 1 calc R . .
C23B C 0.1850(2) 0.09940(17) 0.69296(13) 0.0418(6) Uani 1 1 d . . .
H23B H 0.1059 0.1095 0.7029 0.050 Uiso 1 1 calc R . .
C24B C 0.2313(2) 0.01590(15) 0.69962(11) 0.0360(5) Uani 1 1 d . . .
H24B H 0.1843 -0.0299 0.7144 0.043 Uiso 1 1 calc R . .
C25B C 0.3482(2) 0.00111(15) 0.68411(10) 0.0315(5) Uani 1 1 d . . .
H25B H 0.3802 -0.0551 0.6880 0.038 Uiso 1 1 calc R . .
C26B C 0.41836(17) 0.07002(13) 0.66271(10) 0.0251(4) Uani 1 1 d . . .
H26B H 0.4973 0.0598 0.6524 0.030 Uiso 1 1 calc R . .
C3B C 0.49028(16) 0.37273(12) 0.65967(9) 0.0188(4) Uani 1 1 d . . .
O3B O 0.47761(12) 0.28519(9) 0.68392(6) 0.0223(3) Uani 1 1 d . . .
C31B C 0.61794(16) 0.40069(13) 0.65697(9) 0.0211(4) Uani 1 1 d . . .
H31A H 0.6237 0.4615 0.6433 0.025 Uiso 1 1 calc R . .
H31B H 0.6539 0.3959 0.6978 0.025 Uiso 1 1 calc R . .
C4B C 0.41256(17) 0.43515(14) 0.69785(9) 0.0235(4) Uani 1 1 d . . .
H4B1 H 0.4051 0.4142 0.7403 0.028 Uiso 1 1 calc R . .
H4B2 H 0.4464 0.4939 0.6985 0.028 Uiso 1 1 calc R . .
O4B O 0.29951(11) 0.43569(9) 0.66756(6) 0.0236(3) Uani 1 1 d . . .
C1C C 0.29381(17) 0.64077(12) 0.63512(9) 0.0219(4) Uani 1 1 d . . .
H1C H 0.2771 0.6069 0.6730 0.026 Uiso 1 1 calc R . .
O1C O 0.41030(12) 0.67103(9) 0.63752(6) 0.0252(3) Uani 1 1 d . . .
C11C C 0.4416(2) 0.70750(15) 0.69654(10) 0.0319(5) Uani 1 1 d . . .
H11A H 0.5225 0.7270 0.6955 0.048 Uiso 1 1 calc R . .
H11B H 0.4325 0.6634 0.7282 0.048 Uiso 1 1 calc R . .
H11C H 0.3908 0.7566 0.7056 0.048 Uiso 1 1 calc R . .
C2C C 0.27920(17) 0.58078(12) 0.57906(9) 0.0204(4) Uani 1 1 d . . .
H2C H 0.2002 0.5541 0.5811 0.025 Uiso 1 1 calc R . .
C3C C 0.29015(18) 0.62845(13) 0.51749(9) 0.0231(4) Uani 1 1 d . . .
H3C H 0.3737 0.6390 0.5074 0.028 Uiso 1 1 calc R . .
O3C O 0.23418(14) 0.57895(10) 0.46917(7) 0.0307(3) Uani 1 1 d . . .
C31C C 0.1130(2) 0.60974(14) 0.46313(10) 0.0299(5) Uani 1 1 d . . .
C32C C 0.0265(2) 0.53937(17) 0.48236(11) 0.0405(6) Uani 1 1 d . . .
H32A H 0.0326 0.4902 0.4544 0.061 Uiso 1 1 calc R . .
H32B H -0.0526 0.5626 0.4810 0.061 Uiso 1 1 calc R . .
H32C H 0.0442 0.5204 0.5240 0.061 Uiso 1 1 calc R . .
C33C C 0.0965(2) 0.63990(16) 0.39657(10) 0.0360(5) Uani 1 1 d . . .
H33A H 0.1036 0.5903 0.3691 0.054 Uiso 1 1 calc R . .
H33B H 0.1561 0.6827 0.3864 0.054 Uiso 1 1 calc R . .
H33C H 0.0194 0.6658 0.3919 0.054 Uiso 1 1 calc R . .
C4C C 0.22090(19) 0.71425(13) 0.51641(9) 0.0253(4) Uani 1 1 d . . .
H4C H 0.2472 0.7512 0.4817 0.030 Uiso 1 1 calc R . .
O4C O 0.10337(12) 0.68296(10) 0.50549(7) 0.0287(3) Uani 1 1 d . . .
C5C C 0.22906(18) 0.76493(12) 0.57723(9) 0.0242(4) Uani 1 1 d . . .
H5C H 0.3086 0.7905 0.5804 0.029 Uiso 1 1 calc R . .
O5C O 0.20926(12) 0.71137(8) 0.63027(6) 0.0234(3) Uani 1 1 d . . .
C6C C 0.13888(19) 0.83940(13) 0.57877(10) 0.0265(4) Uani 1 1 d . . .
O61C O 0.04953(15) 0.84012(10) 0.60743(9) 0.0446(5) Uani 1 1 d . . .
O62C O 0.17658(14) 0.90399(10) 0.54166(7) 0.0340(4) Uani 1 1 d . . .
C63C C 0.1005(2) 0.98027(15) 0.53638(13) 0.0414(6) Uani 1 1 d . . .
H63A H 0.1360 1.0223 0.5087 0.062 Uiso 0.50 1 calc PR . .
H63B H 0.0901 1.0065 0.5767 0.062 Uiso 0.50 1 calc PR . .
H63C H 0.0247 0.9626 0.5202 0.062 Uiso 0.50 1 calc PR . .
H63D H 0.0313 0.9720 0.5617 0.062 Uiso 0.50 1 calc PR . .
H63E H 0.0771 0.9878 0.4937 0.062 Uiso 0.50 1 calc PR . .
H63F H 0.1425 1.0317 0.5502 0.062 Uiso 0.50 1 calc PR . .
Cl1 Cl 0.99160(5) 0.54938(4) 0.66488(3) 0.04062(14) Uani 1 1 d . . .
Cl2 Cl 0.77615(7) 0.63382(5) 0.62233(4) 0.0675(2) Uani 1 1 d . . .
C1 C 0.9276(2) 0.64877(16) 0.63716(15) 0.0467(7) Uani 1 1 d . . .
H1D H 0.9381 0.6949 0.6679 0.056 Uiso 1 1 calc R . .
H1E H 0.9674 0.6670 0.5992 0.056 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1A 0.0187(9) 0.0187(9) 0.0267(10) 0.0029(8) -0.0013(8) -0.0014(7)
O1A 0.0173(6) 0.0204(7) 0.0239(7) -0.0053(5) 0.0030(5) -0.0003(5)
C2A 0.0168(9) 0.0273(11) 0.0206(9) 0.0045(8) 0.0008(7) 0.0012(8)
O2A 0.0295(7) 0.0325(8) 0.0210(7) 0.0030(6) -0.0018(6) 0.0101(6)
C21A 0.0177(9) 0.0482(14) 0.0204(10) -0.0004(9) 0.0046(8) 0.0053(9)
O22A 0.0188(7) 0.0825(13) 0.0277(8) -0.0027(8) -0.0072(7) 0.0027(8)
C3A 0.0142(9) 0.0247(10) 0.0211(10) -0.0022(8) 0.0005(7) 0.0007(7)
O3A 0.0201(7) 0.0354(8) 0.0247(7) -0.0004(6) -0.0030(6) -0.0056(6)
C4A 0.0177(9) 0.0189(9) 0.0208(9) 0.0021(7) 0.0023(7) 0.0042(7)
O4A 0.0187(6) 0.0225(7) 0.0272(7) 0.0038(6) 0.0041(6) 0.0049(6)
C41A 0.0211(9) 0.0219(10) 0.0261(10) 0.0004(8) 0.0003(8) -0.0001(8)
O41A 0.0268(8) 0.0329(9) 0.0567(11) 0.0120(8) 0.0157(7) 0.0041(7)
C42A 0.0292(11) 0.0240(11) 0.0399(12) 0.0033(9) 0.0044(9) 0.0032(9)
C5A 0.0183(9) 0.0234(10) 0.0224(9) -0.0009(8) -0.0012(8) 0.0021(7)
O5A 0.0243(7) 0.0226(7) 0.0296(7) -0.0017(6) -0.0072(6) -0.0010(6)
C6A 0.0504(14) 0.0378(14) 0.0218(10) -0.0002(9) -0.0036(10) 0.0041(11)
C1B 0.0217(9) 0.0216(10) 0.0165(9) 0.0000(7) -0.0026(7) 0.0011(8)
O1B 0.0228(6) 0.0191(6) 0.0222(7) 0.0006(6) 0.0009(6) 0.0054(5)
C2B 0.0224(9) 0.0192(9) 0.0171(9) 0.0004(8) -0.0021(7) 0.0025(7)
O2B 0.0305(7) 0.0175(6) 0.0175(6) 0.0011(5) -0.0064(6) -0.0001(6)
C20B 0.0203(9) 0.0209(10) 0.0182(9) 0.0009(8) 0.0005(7) 0.0034(7)
C21B 0.0209(9) 0.0236(10) 0.0185(9) 0.0023(8) -0.0031(8) -0.0003(8)
C22B 0.0281(11) 0.0294(12) 0.0425(13) 0.0110(10) 0.0033(10) 0.0055(9)
C23B 0.0226(11) 0.0480(15) 0.0546(16) 0.0140(13) 0.0066(11) 0.0018(10)
C24B 0.0320(12) 0.0353(13) 0.0407(13) 0.0123(10) -0.0010(10) -0.0096(10)
C25B 0.0368(12) 0.0249(11) 0.0328(12) 0.0032(9) -0.0012(10) 0.0011(9)
C26B 0.0228(10) 0.0254(10) 0.0270(10) 0.0011(9) 0.0020(8) 0.0016(8)
C3B 0.0216(9) 0.0189(9) 0.0159(9) -0.0007(7) -0.0021(7) 0.0026(8)
O3B 0.0260(7) 0.0228(7) 0.0181(7) 0.0044(5) -0.0041(5) 0.0009(6)
C31B 0.0214(9) 0.0208(9) 0.0210(9) -0.0053(8) 0.0007(8) 0.0017(8)
C4B 0.0230(10) 0.0313(11) 0.0163(9) -0.0025(8) -0.0014(7) 0.0071(8)
O4B 0.0220(7) 0.0309(8) 0.0179(7) 0.0006(6) 0.0025(5) 0.0063(6)
C1C 0.0264(10) 0.0213(10) 0.0179(9) 0.0010(8) -0.0004(8) 0.0035(8)
O1C 0.0267(7) 0.0302(8) 0.0186(7) -0.0011(6) -0.0015(5) -0.0010(6)
C11C 0.0396(12) 0.0344(13) 0.0218(11) 0.0004(9) -0.0056(9) -0.0073(10)
C2C 0.0191(9) 0.0202(9) 0.0219(9) -0.0011(8) -0.0005(8) 0.0052(7)
C3C 0.0295(10) 0.0211(10) 0.0186(9) -0.0004(8) 0.0015(8) 0.0033(8)
O3C 0.0416(9) 0.0297(8) 0.0209(7) -0.0049(6) -0.0055(6) 0.0119(7)
C31C 0.0410(12) 0.0251(11) 0.0236(10) -0.0018(8) -0.0060(9) 0.0068(10)
C32C 0.0502(14) 0.0427(14) 0.0285(12) -0.0012(10) -0.0073(10) -0.0044(12)
C33C 0.0475(14) 0.0358(13) 0.0247(11) 0.0000(10) -0.0076(10) 0.0065(11)
C4C 0.0311(10) 0.0245(10) 0.0201(10) 0.0036(8) 0.0006(8) 0.0022(9)
O4C 0.0316(8) 0.0301(8) 0.0243(7) -0.0025(6) -0.0051(6) 0.0076(6)
C5C 0.0279(10) 0.0194(10) 0.0253(10) 0.0022(8) 0.0022(8) 0.0010(8)
O5C 0.0316(7) 0.0204(7) 0.0181(7) 0.0012(5) 0.0030(6) 0.0051(6)
C6C 0.0346(11) 0.0178(10) 0.0270(10) -0.0016(8) -0.0027(9) 0.0011(8)
O61C 0.0449(10) 0.0275(8) 0.0615(12) 0.0100(8) 0.0229(9) 0.0113(7)
O62C 0.0418(9) 0.0222(8) 0.0379(9) 0.0089(7) 0.0001(7) 0.0024(6)
C63C 0.0477(14) 0.0203(11) 0.0562(16) 0.0127(11) -0.0081(13) 0.0007(10)
Cl1 0.0483(3) 0.0323(3) 0.0412(3) 0.0029(3) 0.0052(3) -0.0001(3)
Cl2 0.0566(4) 0.0619(5) 0.0841(6) 0.0319(4) -0.0193(4) -0.0065(4)
C1 0.0489(15) 0.0314(13) 0.0596(18) 0.0035(13) -0.0087(13) -0.0053(11)

_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
C1A O5A 1.390(2) . ?
C1A O1A 1.416(2) . ?
C1A C2A 1.512(3) . ?
C1A H1A 0.9800 . ?
O1A C31B 1.429(2) . ?
C2A O2A 1.433(2) . ?
C2A C3A 1.546(3) . ?
C2A H2A 0.9800 . ?
O2A C21A 1.337(3) . ?
C21A O22A 1.193(2) . ?
C21A O3A 1.341(3) . ?
C3A O3A 1.439(2) . ?
C3A C4A 1.517(3) . ?
C3A H3A 0.9800 . ?
C4A O4A 1.442(2) . ?
C4A C5A 1.528(3) . ?
C4A H4A 0.9800 . ?
O4A C41A 1.347(2) . ?
C41A O41A 1.199(2) . ?
C41A C42A 1.498(3) . ?
C42A H42A 0.9600 . ?
C42A H42B 0.9600 . ?
C42A H42C 0.9600 . ?
C5A O5A 1.444(2) . ?
C5A C6A 1.508(3) . ?
C5A H5A 0.9800 . ?
C6A H6A1 0.9600 . ?
C6A H6A2 0.9600 . ?
C6A H6A3 0.9600 . ?
C1B O1B 1.398(2) . ?
C1B O4B 1.415(2) . ?
C1B C2B 1.519(3) . ?
C1B H1B 0.9800 . ?
O1B C2C 1.427(2) . ?
C2B O2B 1.421(2) . ?
C2B C3B 1.543(3) . ?
C2B H2B 0.9800 . ?
O2B C20B 1.418(2) . ?
C20B O3B 1.418(2) . ?
C20B C21B 1.511(3) . ?
C20B H20B 0.9800 . ?
C21B C26B 1.373(3) . ?
C21B C22B 1.389(3) . ?
C22B C23B 1.375(3) . ?
C22B H22B 0.9300 . ?
C23B C24B 1.379(3) . ?
C23B H23B 0.9300 . ?
C24B C25B 1.378(3) . ?
C24B H24B 0.9300 . ?
C25B C26B 1.390(3) . ?
C25B H25B 0.9300 . ?
C26B H26B 0.9300 . ?
C3B O3B 1.434(2) . ?
C3B C31B 1.502(3) . ?
C3B C4B 1.529(3) . ?
C31B H31A 0.9700 . ?
C31B H31B 0.9700 . ?
C4B O4B 1.432(2) . ?
C4B H4B1 0.9700 . ?
C4B H4B2 0.9700 . ?
C1C O1C 1.393(2) . ?
C1C O5C 1.438(2) . ?
C1C C2C 1.519(3) . ?
C1C H1C 0.9800 . ?
O1C C11C 1.428(2) . ?
C11C H11A 0.9600 . ?
C11C H11B 0.9600 . ?
C11C H11C 0.9600 . ?
C2C C3C 1.513(3) . ?
C2C H2C 0.9800 . ?
C3C O3C 1.429(2) . ?
C3C C4C 1.519(3) . ?
C3C H3C 0.9800 . ?
O3C C31C 1.450(3) . ?
C31C O4C 1.440(3) . ?
C31C C32C 1.505(3) . ?
C31C C33C 1.513(3) . ?
C32C H32A 0.9600 . ?
C32C H32B 0.9600 . ?
C32C H32C 0.9600 . ?
C33C H33A 0.9600 . ?
C33C H33B 0.9600 . ?
C33C H33C 0.9600 . ?
C4C O4C 1.428(3) . ?
C4C C5C 1.519(3) . ?
C4C H4C 0.9800 . ?
C5C O5C 1.417(2) . ?
C5C C6C 1.521(3) . ?
C5C H5C 0.9800 . ?
C6C O61C 1.181(3) . ?
C6C O62C 1.333(3) . ?
O62C C63C 1.446(3) . ?
C63C H63A 0.9600 . ?
C63C H63B 0.9600 . ?
C63C H63C 0.9600 . ?
C63C H63D 0.9600 . ?
C63C H63E 0.9600 . ?
C63C H63F 0.9600 . ?
Cl1 C1 1.775(3) . ?
Cl2 C1 1.753(3) . ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5A C1A O1A 112.77(16) . . ?
O5A C1A C2A 111.05(15) . . ?
O1A C1A C2A 106.16(15) . . ?
O5A C1A H1A 108.9 . . ?
O1A C1A H1A 108.9 . . ?
C2A C1A H1A 108.9 . . ?
C1A O1A C31B 114.28(14) . . ?
O2A C2A C1A 109.83(15) . . ?
O2A C2A C3A 103.38(15) . . ?
C1A C2A C3A 111.29(15) . . ?
O2A C2A H2A 110.7 . . ?
C1A C2A H2A 110.7 . . ?
C3A C2A H2A 110.7 . . ?
C21A O2A C2A 109.97(15) . . ?
O22A C21A O2A 124.3(2) . . ?
O22A C21A O3A 123.5(2) . . ?
O2A C21A O3A 112.26(16) . . ?
O3A C3A C4A 111.71(15) . . ?
O3A C3A C2A 103.19(15) . . ?
C4A C3A C2A 112.12(16) . . ?
O3A C3A H3A 109.9 . . ?
C4A C3A H3A 109.9 . . ?
C2A C3A H3A 109.9 . . ?
C21A O3A C3A 109.79(15) . . ?
O4A C4A C3A 108.13(15) . . ?
O4A C4A C5A 107.68(14) . . ?
C3A C4A C5A 109.52(15) . . ?
O4A C4A H4A 110.5 . . ?
C3A C4A H4A 110.5 . . ?
C5A C4A H4A 110.5 . . ?
C41A O4A C4A 117.37(14) . . ?
O41A C41A O4A 123.76(18) . . ?
O41A C41A C42A 124.87(19) . . ?
O4A C41A C42A 111.37(16) . . ?
C41A C42A H42A 109.5 . . ?
C41A C42A H42B 109.5 . . ?
H42A C42A H42B 109.5 . . ?
C41A C42A H42C 109.5 . . ?
H42A C42A H42C 109.5 . . ?
H42B C42A H42C 109.5 . . ?
O5A C5A C6A 106.24(16) . . ?
O5A C5A C4A 111.90(15) . . ?
C6A C5A C4A 112.31(17) . . ?
O5A C5A H5A 108.8 . . ?
C6A C5A H5A 108.8 . . ?
C4A C5A H5A 108.8 . . ?
C1A O5A C5A 117.76(14) . . ?
C5A C6A H6A1 109.5 . . ?
C5A C6A H6A2 109.5 . . ?
H6A1 C6A H6A2 109.5 . . ?
C5A C6A H6A3 109.5 . . ?
H6A1 C6A H6A3 109.5 . . ?
H6A2 C6A H6A3 109.5 . . ?
O1B C1B O4B 112.53(15) . . ?
O1B C1B C2B 104.71(15) . . ?
O4B C1B C2B 105.88(14) . . ?
O1B C1B H1B 111.1 . . ?
O4B C1B H1B 111.1 . . ?
C2B C1B H1B 111.1 . . ?
C1B O1B C2C 114.56(14) . . ?
O2B C2B C1B 109.83(15) . . ?
O2B C2B C3B 105.25(14) . . ?
C1B C2B C3B 103.91(15) . . ?
O2B C2B H2B 112.4 . . ?
C1B C2B H2B 112.4 . . ?
C3B C2B H2B 112.4 . . ?
C20B O2B C2B 107.89(14) . . ?
O2B C20B O3B 105.56(14) . . ?
O2B C20B C21B 110.20(15) . . ?
O3B C20B C21B 110.41(15) . . ?
O2B C20B H20B 110.2 . . ?
O3B C20B H20B 110.2 . . ?
C21B C20B H20B 110.2 . . ?
C26B C21B C22B 119.60(18) . . ?
C26B C21B C20B 120.17(17) . . ?
C22B C21B C20B 120.22(17) . . ?
C23B C22B C21B 119.7(2) . . ?
C23B C22B H22B 120.2 . . ?
C21B C22B H22B 120.2 . . ?
C22B C23B C24B 121.1(2) . . ?
C22B C23B H23B 119.5 . . ?
C24B C23B H23B 119.5 . . ?
C25B C24B C23B 119.2(2) . . ?
C25B C24B H24B 120.4 . . ?
C23B C24B H24B 120.4 . . ?
C24B C25B C26B 120.1(2) . . ?
C24B C25B H25B 119.9 . . ?
C26B C25B H25B 119.9 . . ?
C21B C26B C25B 120.29(19) . . ?
C21B C26B H26B 119.9 . . ?
C25B C26B H26B 119.9 . . ?
O3B C3B C31B 111.79(15) . . ?
O3B C3B C4B 108.79(15) . . ?
C31B C3B C4B 113.28(16) . . ?
O3B C3B C2B 103.75(14) . . ?
C31B C3B C2B 114.74(16) . . ?
C4B C3B C2B 103.75(14) . . ?
C20B O3B C3B 108.33(13) . . ?
O1A C31B C3B 107.69(15) . . ?
O1A C31B H31A 110.2 . . ?
C3B C31B H31A 110.2 . . ?
O1A C31B H31B 110.2 . . ?
C3B C31B H31B 110.2 . . ?
H31A C31B H31B 108.5 . . ?
O4B C4B C3B 105.69(15) . . ?
O4B C4B H4B1 110.6 . . ?
C3B C4B H4B1 110.6 . . ?
O4B C4B H4B2 110.6 . . ?
C3B C4B H4B2 110.6 . . ?
H4B1 C4B H4B2 108.7 . . ?
C1B O4B C4B 105.95(14) . . ?
O1C C1C O5C 112.49(15) . . ?
O1C C1C C2C 109.23(15) . . ?
O5C C1C C2C 108.50(14) . . ?
O1C C1C H1C 108.9 . . ?
O5C C1C H1C 108.9 . . ?
C2C C1C H1C 108.9 . . ?
C1C O1C C11C 113.19(15) . . ?
O1C C11C H11A 109.5 . . ?
O1C C11C H11B 109.5 . . ?
H11A C11C H11B 109.5 . . ?
O1C C11C H11C 109.5 . . ?
H11A C11C H11C 109.5 . . ?
H11B C11C H11C 109.5 . . ?
O1B C2C C3C 107.35(15) . . ?
O1B C2C C1C 111.54(15) . . ?
C3C C2C C1C 113.43(15) . . ?
O1B C2C H2C 108.1 . . ?
C3C C2C H2C 108.1 . . ?
C1C C2C H2C 108.1 . . ?
O3C C3C C2C 110.34(16) . . ?
O3C C3C C4C 102.27(15) . . ?
C2C C3C C4C 112.43(16) . . ?
O3C C3C H3C 110.5 . . ?
C2C C3C H3C 110.5 . . ?
C4C C3C H3C 110.5 . . ?
C3C O3C C31C 108.18(15) . . ?
O4C C31C O3C 105.26(16) . . ?
O4C C31C C32C 108.98(19) . . ?
O3C C31C C32C 110.97(18) . . ?
O4C C31C C33C 110.75(17) . . ?
O3C C31C C33C 107.35(18) . . ?
C32C C31C C33C 113.23(19) . . ?
C31C C32C H32A 109.5 . . ?
C31C C32C H32B 109.5 . . ?
H32A C32C H32B 109.5 . . ?
C31C C32C H32C 109.5 . . ?
H32A C32C H32C 109.5 . . ?
H32B C32C H32C 109.5 . . ?
C31C C33C H33A 109.5 . . ?
C31C C33C H33B 109.5 . . ?
H33A C33C H33B 109.5 . . ?
C31C C33C H33C 109.5 . . ?
H33A C33C H33C 109.5 . . ?
H33B C33C H33C 109.5 . . ?
O4C C4C C3C 101.24(16) . . ?
O4C C4C C5C 111.48(16) . . ?
C3C C4C C5C 112.95(16) . . ?
O4C C4C H4C 110.3 . . ?
C3C C4C H4C 110.3 . . ?
C5C C4C H4C 110.3 . . ?
C4C O4C C31C 106.88(15) . . ?
O5C C5C C4C 113.04(15) . . ?
O5C C5C C6C 107.66(16) . . ?
C4C C5C C6C 110.76(16) . . ?
O5C C5C H5C 108.4 . . ?
C4C C5C H5C 108.4 . . ?
C6C C5C H5C 108.4 . . ?
C5C O5C C1C 112.40(14) . . ?
O61C C6C O62C 125.25(19) . . ?
O61C C6C C5C 126.08(19) . . ?
O62C C6C C5C 108.67(17) . . ?
C6C O62C C63C 116.51(18) . . ?
O62C C63C H63A 109.5 . . ?
O62C C63C H63B 109.5 . . ?
H63A C63C H63B 109.5 . . ?
O62C C63C H63C 109.5 . . ?
H63A C63C H63C 109.5 . . ?
H63B C63C H63C 109.5 . . ?
O62C C63C H63D 109.5 . . ?
H63A C63C H63D 141.1 . . ?
H63B C63C H63D 56.3 . . ?
H63C C63C H63D 56.3 . . ?
O62C C63C H63E 109.5 . . ?
H63A C63C H63E 56.3 . . ?
H63B C63C H63E 141.1 . . ?
H63C C63C H63E 56.3 . . ?
H63D C63C H63E 109.5 . . ?
O62C C63C H63F 109.5 . . ?
H63A C63C H63F 56.3 . . ?
H63B C63C H63F 56.3 . . ?
H63C C63C H63F 141.1 . . ?
H63D C63C H63F 109.5 . . ?
H63E C63C H63F 109.5 . . ?
Cl2 C1 Cl1 110.31(14) . . ?
Cl2 C1 H1D 109.6 . . ?
Cl1 C1 H1D 109.6 . . ?
Cl2 C1 H1E 109.6 . . ?
Cl1 C1 H1E 109.6 . . ?
H1D C1 H1E 108.1 . . ?

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
O5A C1A O1A C31B 70.97(19) . . . . ?
C2A C1A O1A C31B -167.22(15) . . . . ?
O5A C1A C2A O2A 172.32(15) . . . . ?
O1A C1A C2A O2A 49.42(19) . . . . ?
O5A C1A C2A C3A 58.47(19) . . . . ?
O1A C1A C2A C3A -64.44(18) . . . . ?
C1A C2A O2A C21A -108.14(17) . . . . ?
C3A C2A O2A C21A 10.71(19) . . . . ?
C2A O2A C21A O22A 174.48(19) . . . . ?
C2A O2A C21A O3A -5.7(2) . . . . ?
O2A C2A C3A O3A -11.49(17) . . . . ?
C1A C2A C3A O3A 106.33(16) . . . . ?
O2A C2A C3A C4A -131.85(15) . . . . ?
C1A C2A C3A C4A -14.0(2) . . . . ?
O22A C21A O3A C3A 177.26(19) . . . . ?
O2A C21A O3A C3A -2.6(2) . . . . ?
C4A C3A O3A C21A 129.50(17) . . . . ?
C2A C3A O3A C21A 8.87(19) . . . . ?
O3A C3A C4A O4A 87.13(17) . . . . ?
C2A C3A C4A O4A -157.60(14) . . . . ?
O3A C3A C4A C5A -155.80(15) . . . . ?
C2A C3A C4A C5A -40.5(2) . . . . ?
C3A C4A O4A C41A -126.65(17) . . . . ?
C5A C4A O4A C41A 115.09(17) . . . . ?
C4A O4A C41A O41A 2.0(3) . . . . ?
C4A O4A C41A C42A -177.81(17) . . . . ?
O4A C4A C5A O5A 175.15(14) . . . . ?
C3A C4A C5A O5A 57.8(2) . . . . ?
O4A C4A C5A C6A -65.5(2) . . . . ?
C3A C4A C5A C6A 177.18(17) . . . . ?
O1A C1A O5A C5A 75.4(2) . . . . ?
C2A C1A O5A C5A -43.6(2) . . . . ?
C6A C5A O5A C1A -137.29(17) . . . . ?
C4A C5A O5A C1A -14.4(2) . . . . ?
O4B C1B O1B C2C -67.53(19) . . . . ?
C2B C1B O1B C2C 177.93(15) . . . . ?
O1B C1B C2B O2B -153.28(14) . . . . ?
O4B C1B C2B O2B 87.60(17) . . . . ?
O1B C1B C2B C3B 94.54(16) . . . . ?
O4B C1B C2B C3B -24.58(19) . . . . ?
C1B C2B O2B C20B -129.91(15) . . . . ?
C3B C2B O2B C20B -18.61(18) . . . . ?
C2B O2B C20B O3B 30.10(18) . . . . ?
C2B O2B C20B C21B 149.32(15) . . . . ?
O2B C20B C21B C26B 137.57(18) . . . . ?
O3B C20B C21B C26B -106.2(2) . . . . ?
O2B C20B C21B C22B -42.8(2) . . . . ?
O3B C20B C21B C22B 73.4(2) . . . . ?
C26B C21B C22B C23B 0.0(3) . . . . ?
C20B C21B C22B C23B -179.6(2) . . . . ?
C21B C22B C23B C24B 0.5(4) . . . . ?
C22B C23B C24B C25B -0.8(4) . . . . ?
C23B C24B C25B C26B 0.7(4) . . . . ?
C22B C21B C26B C25B -0.2(3) . . . . ?
C20B C21B C26B C25B 179.44(19) . . . . ?
C24B C25B C26B C21B -0.2(3) . . . . ?
O2B C2B C3B O3B 0.52(18) . . . . ?
C1B C2B C3B O3B 115.97(15) . . . . ?
O2B C2B C3B C31B 122.76(16) . . . . ?
C1B C2B C3B C31B -121.78(17) . . . . ?
O2B C2B C3B C4B -113.13(16) . . . . ?
C1B C2B C3B C4B 2.32(19) . . . . ?
O2B C20B O3B C3B -29.88(18) . . . . ?
C21B C20B O3B C3B -148.96(15) . . . . ?
C31B C3B O3B C20B -106.39(16) . . . . ?
C4B C3B O3B C20B 127.77(15) . . . . ?
C2B C3B O3B C20B 17.79(17) . . . . ?
C1A O1A C31B C3B 173.80(15) . . . . ?
O3B C3B C31B O1A 63.99(19) . . . . ?
C4B C3B C31B O1A -172.67(15) . . . . ?
C2B C3B C31B O1A -53.8(2) . . . . ?
O3B C3B C4B O4B -89.66(17) . . . . ?
C31B C3B C4B O4B 145.37(16) . . . . ?
C2B C3B C4B O4B 20.3(2) . . . . ?
O1B C1B O4B C4B -74.98(18) . . . . ?
C2B C1B O4B C4B 38.85(19) . . . . ?
C3B C4B O4B C1B -37.13(19) . . . . ?
O5C C1C O1C C11C 75.6(2) . . . . ?
C2C C1C O1C C11C -163.87(16) . . . . ?
C1B O1B C2C C3C -137.40(16) . . . . ?
C1B O1B C2C C1C 97.76(18) . . . . ?
O1C C1C C2C O1B 54.0(2) . . . . ?
O5C C1C C2C O1B 176.96(14) . . . . ?
O1C C1C C2C C3C -67.36(19) . . . . ?
O5C C1C C2C C3C 55.6(2) . . . . ?
O1B C2C C3C O3C 77.66(19) . . . . ?
C1C C2C C3C O3C -158.65(15) . . . . ?
O1B C2C C3C C4C -168.87(16) . . . . ?
C1C C2C C3C C4C -45.2(2) . . . . ?
C2C C3C O3C C31C 93.03(18) . . . . ?
C4C C3C O3C C31C -26.78(19) . . . . ?
C3C O3C C31C O4C 4.6(2) . . . . ?
C3C O3C C31C C32C -113.16(19) . . . . ?
C3C O3C C31C C33C 122.63(18) . . . . ?
O3C C3C C4C O4C 38.86(18) . . . . ?
C2C C3C C4C O4C -79.48(19) . . . . ?
O3C C3C C4C C5C 158.18(16) . . . . ?
C2C C3C C4C C5C 39.8(2) . . . . ?
C3C C4C O4C C31C -37.23(18) . . . . ?
C5C C4C O4C C31C -157.59(16) . . . . ?
O3C C31C O4C C4C 21.5(2) . . . . ?
C32C C31C O4C C4C 140.56(18) . . . . ?
C33C C31C O4C C4C -94.2(2) . . . . ?
O4C C4C C5C O5C 66.0(2) . . . . ?
C3C C4C C5C O5C -47.2(2) . . . . ?
O4C C4C C5C C6C -54.9(2) . . . . ?
C3C C4C C5C C6C -168.13(17) . . . . ?
C4C C5C O5C C1C 60.1(2) . . . . ?
C6C C5C O5C C1C -177.22(15) . . . . ?
O1C C1C O5C C5C 57.9(2) . . . . ?
C2C C1C O5C C5C -63.05(19) . . . . ?
O5C C5C C6C O61C -19.3(3) . . . . ?
C4C C5C C6C O61C 104.8(3) . . . . ?
O5C C5C C6C O62C 161.39(16) . . . . ?
C4C C5C C6C O62C -74.6(2) . . . . ?
O61C C6C O62C C63C -0.4(3) . . . . ?
C5C C6C O62C C63C 178.92(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.044