# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_13spz2h
#TrackingRef '17189_web_deposit_cif_file_1_ShengpingZheng_1359062557.13spz2h.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H11 Cl O3'
_chemical_formula_weight         202.63

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   5.2268(5)
_cell_length_b                   8.9268(9)
_cell_length_c                   19.809(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.227(2)
_cell_angle_gamma                90.00
_cell_volume                     923.59(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9941
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      28.49

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8196
_exptl_absorpt_correction_T_max  0.9238
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19279
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0104
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         28.49
_reflns_number_total             2312
_reflns_number_gt                2246
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0342P)²+0.4173P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2312
_refine_ls_number_parameters     126
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0699
_refine_ls_wR_factor_gt          0.0694
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.72171(5) 0.30994(3) 0.089241(12) 0.01932(8) Uani 1 1 d . . .
O1 O 0.59696(14) 0.45612(9) 0.33668(3) 0.01759(16) Uani 1 1 d . . .
O2 O 0.63349(14) 0.16443(8) 0.45716(4) 0.01781(16) Uani 1 1 d D . .
H2O H 0.731(3) 0.1175(17) 0.4833(7) 0.036(4) Uiso 1 1 d D . .
O3 O 0.30364(14) 0.52223(9) 0.06639(3) 0.01717(16) Uani 1 1 d D . .
H3O H 0.165(2) 0.5693(17) 0.0632(8) 0.036(4) Uiso 1 1 d D . .
C1 C 0.53203(18) 0.46773(11) 0.26913(5) 0.01359(18) Uani 1 1 d . . .
C2 C 0.33313(18) 0.56652(11) 0.25169(5) 0.01438(18) Uani 1 1 d . . .
H2 H 0.2527 0.6219 0.2859 0.017 Uiso 1 1 calc R . .
C3 C 0.25256(18) 0.58402(11) 0.18452(5) 0.01462(19) Uani 1 1 d . . .
H3 H 0.1159 0.6508 0.1733 0.018 Uiso 1 1 calc R . .
C4 C 0.36965(18) 0.50479(11) 0.13322(5) 0.01317(18) Uani 1 1 d . . .
C5 C 0.56812(18) 0.40777(11) 0.15171(5) 0.01325(18) Uani 1 1 d . . .
C6 C 0.65121(18) 0.38763(11) 0.21885(5) 0.01407(18) Uani 1 1 d . . .
H6 H 0.7870 0.3203 0.2301 0.017 Uiso 1 1 calc R . .
C7 C 0.82364(18) 0.37157(12) 0.35434(5) 0.01603(19) Uani 1 1 d . . .
H7A H 0.9710 0.4104 0.3297 0.019 Uiso 1 1 calc R . .
H7B H 0.7984 0.2648 0.3423 0.019 Uiso 1 1 calc R . .
C8 C 0.87306(19) 0.38801(12) 0.42990(5) 0.0167(2) Uani 1 1 d . . .
H8A H 0.8905 0.4957 0.4411 0.020 Uiso 1 1 calc R . .
H8B H 1.0371 0.3384 0.4429 0.020 Uiso 1 1 calc R . .
C9 C 0.66197(19) 0.32107(11) 0.47090(5) 0.0160(2) Uani 1 1 d . . .
H9A H 0.7033 0.3359 0.5196 0.019 Uiso 1 1 calc R . .
H9B H 0.4986 0.3731 0.4597 0.019 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
Cl1 0.02488(14) 0.01820(13) 0.01499(13) -0.00193(8) 0.00238(9) 0.00626(9)
O1 0.0200(4) 0.0214(4) 0.0111(3) 0.0013(3) -0.0031(3) 0.0058(3)
O2 0.0196(4) 0.0160(3) 0.0174(3) 0.0040(3) -0.0054(3) -0.0040(3)
O3 0.0192(4) 0.0209(4) 0.0110(3) -0.0001(3) -0.0033(3) 0.0046(3)
C1 0.0151(4) 0.0144(4) 0.0112(4) 0.0022(3) -0.0014(3) -0.0014(3)
C2 0.0143(4) 0.0157(4) 0.0132(4) 0.0001(3) 0.0008(3) 0.0009(3)
C3 0.0130(4) 0.0164(4) 0.0143(4) 0.0011(3) -0.0012(3) 0.0021(3)
C4 0.0139(4) 0.0137(4) 0.0117(4) 0.0011(3) -0.0015(3) -0.0018(3)
C5 0.0152(4) 0.0121(4) 0.0126(4) -0.0004(3) 0.0015(3) -0.0003(3)
C6 0.0144(4) 0.0135(4) 0.0142(4) 0.0023(3) -0.0009(3) 0.0015(3)
C7 0.0133(4) 0.0201(5) 0.0145(4) 0.0045(4) -0.0017(3) 0.0006(4)
C8 0.0168(4) 0.0174(5) 0.0155(4) 0.0033(4) -0.0052(3) -0.0041(4)
C9 0.0177(5) 0.0172(5) 0.0129(4) 0.0001(3) -0.0019(3) -0.0001(3)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C5 1.7366(10) . ?
O1 C1 1.3716(11) . ?
O1 C7 1.4365(12) . ?
O2 C9 1.4312(12) . ?
O2 H2O 0.826(9) . ?
O3 C4 1.3639(11) . ?
O3 H3O 0.836(9) . ?
C1 C6 1.3928(13) . ?
C1 C2 1.3964(13) . ?
C2 C3 1.3888(13) . ?
C2 H2 0.9500 . ?
C3 C4 1.3985(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.3896(13) . ?
C5 C6 1.3945(13) . ?
C6 H6 0.9500 . ?
C7 C8 1.5161(13) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5179(14) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C7 116.60(8) . . ?
C9 O2 H2O 108.6(12) . . ?
C4 O3 H3O 108.4(11) . . ?
O1 C1 C6 123.95(9) . . ?
O1 C1 C2 116.28(8) . . ?
C6 C1 C2 119.78(9) . . ?
C3 C2 C1 120.21(9) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.96(9) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
O3 C4 C5 119.02(9) . . ?
O3 C4 C3 123.11(9) . . ?
C5 C4 C3 117.83(8) . . ?
C4 C5 C6 122.24(9) . . ?
C4 C5 Cl1 119.11(7) . . ?
C6 C5 Cl1 118.64(7) . . ?
C1 C6 C5 118.98(9) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
O1 C7 C8 107.26(8) . . ?
O1 C7 H7A 110.3 . . ?
C8 C7 H7A 110.3 . . ?
O1 C7 H7B 110.3 . . ?
C8 C7 H7B 110.3 . . ?
H7A C7 H7B 108.5 . . ?
C7 C8 C9 113.00(8) . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
O2 C9 C8 110.81(8) . . ?
O2 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.49
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 921686'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_13spz12h2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H9 Cl O3'
_chemical_formula_weight         188.60

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   20.214(3)
_cell_length_b                   10.0193(13)
_cell_length_c                   8.1960(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.8337(18)
_cell_angle_gamma                90.00
_cell_volume                     1651.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9946
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8357
_exptl_absorpt_correction_T_max  0.9669
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24945
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0143
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         28.29
_reflns_number_total             4092
_reflns_number_gt                3775
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0256P)²+0.9189P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4092
_refine_ls_number_parameters     229
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0662
_refine_ls_wR_factor_gt          0.0643
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.650566(13) 0.75728(3) 0.54493(3) 0.01970(7) Uani 1 1 d . . .
O1 O 0.67152(4) 0.97987(8) 0.33080(10) 0.01491(16) Uani 1 1 d D . .
H1O H 0.6771(7) 1.0515(11) 0.2814(17) 0.022 Uiso 1 1 d D . .
O2 O 0.40829(4) 0.83787(8) 0.36423(10) 0.01554(16) Uani 1 1 d . . .
O3 O 0.28886(4) 0.69419(8) 0.31976(11) 0.01913(18) Uani 1 1 d D . .
H3O H 0.2514(5) 0.6700(16) 0.3407(19) 0.029 Uiso 1 1 d D . .
C1 C 0.60560(5) 0.94917(11) 0.33058(13) 0.0120(2) Uani 1 1 d . . .
C2 C 0.58791(5) 0.84532(11) 0.43068(13) 0.0124(2) Uani 1 1 d . . .
C3 C 0.52218(5) 0.80962(11) 0.43938(13) 0.0129(2) Uani 1 1 d . . .
H3 H 0.5113 0.7397 0.5103 0.016 Uiso 1 1 calc R . .
C4 C 0.47213(5) 0.87719(11) 0.34308(13) 0.0126(2) Uani 1 1 d . . .
C5 C 0.48874(5) 0.97882(11) 0.23867(13) 0.0143(2) Uani 1 1 d . . .
H5 H 0.4549 1.0237 0.1709 0.017 Uiso 1 1 calc R . .
C6 C 0.55528(5) 1.01461(11) 0.23389(13) 0.0140(2) Uani 1 1 d . . .
H6 H 0.5663 1.0847 0.1635 0.017 Uiso 1 1 calc R . .
C7 C 0.35691(5) 0.87498(12) 0.23992(15) 0.0186(2) Uani 1 1 d . . .
H7A H 0.3632 0.8286 0.1359 0.022 Uiso 1 1 calc R . .
H7B H 0.3581 0.9724 0.2204 0.022 Uiso 1 1 calc R . .
C8 C 0.29137(5) 0.83576(12) 0.29838(16) 0.0191(2) Uani 1 1 d . . .
H8A H 0.2860 0.8808 0.4037 0.023 Uiso 1 1 calc R . .
H8B H 0.2545 0.8645 0.2172 0.023 Uiso 1 1 calc R . .
Cl2 Cl 1.153405(13) 0.79662(3) 0.51434(3) 0.01903(7) Uani 1 1 d . . .
O4 O 1.17121(4) 0.54214(8) 0.35464(10) 0.01407(16) Uani 1 1 d D . .
H4O H 1.1763(7) 0.4707(11) 0.3039(16) 0.021 Uiso 1 1 d D . .
O5 O 0.90962(4) 0.69697(8) 0.38669(10) 0.01502(16) Uani 1 1 d . . .
O6 O 0.78644(4) 0.82846(8) 0.29972(11) 0.02051(18) Uani 1 1 d D . .
H6O H 0.7509(6) 0.8590(16) 0.3239(19) 0.031 Uiso 1 1 d D . .
C9 C 1.10548(5) 0.57581(11) 0.35360(13) 0.0122(2) Uani 1 1 d . . .
C10 C 1.08946(5) 0.69358(11) 0.43098(13) 0.0125(2) Uani 1 1 d . . .
C11 C 1.02404(5) 0.73168(11) 0.44106(13) 0.0129(2) Uani 1 1 d . . .
H11 H 1.0143 0.8109 0.4976 0.015 Uiso 1 1 calc R . .
C12 C 0.97280(5) 0.65245(11) 0.36739(13) 0.0125(2) Uani 1 1 d . . .
C13 C 0.98763(5) 0.53675(11) 0.28422(13) 0.0140(2) Uani 1 1 d . . .
H13 H 0.9528 0.4838 0.2312 0.017 Uiso 1 1 calc R . .
C14 C 1.05384(5) 0.49901(11) 0.27920(13) 0.0139(2) Uani 1 1 d . . .
H14 H 1.0637 0.4193 0.2238 0.017 Uiso 1 1 calc R . .
C15 C 0.85562(5) 0.63384(11) 0.28992(14) 0.0153(2) Uani 1 1 d . . .
H15A H 0.8571 0.5361 0.3080 0.018 Uiso 1 1 calc R . .
H15B H 0.8586 0.6513 0.1720 0.018 Uiso 1 1 calc R . .
C16 C 0.79188(5) 0.69036(11) 0.34100(14) 0.0157(2) Uani 1 1 d . . .
H16A H 0.7536 0.6412 0.2851 0.019 Uiso 1 1 calc R . .
H16B H 0.7910 0.6793 0.4608 0.019 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
Cl1 0.01123(13) 0.02527(15) 0.02206(14) 0.01082(11) -0.00089(10) 0.00059(10)
O1 0.0091(3) 0.0139(4) 0.0220(4) 0.0032(3) 0.0034(3) -0.0007(3)
O2 0.0077(3) 0.0197(4) 0.0190(4) -0.0004(3) 0.0005(3) -0.0018(3)
O3 0.0106(4) 0.0147(4) 0.0330(5) -0.0048(3) 0.0066(3) -0.0017(3)
C1 0.0098(5) 0.0118(5) 0.0147(5) -0.0027(4) 0.0030(4) -0.0006(4)
C2 0.0102(5) 0.0139(5) 0.0127(5) 0.0001(4) 0.0001(4) 0.0018(4)
C3 0.0123(5) 0.0136(5) 0.0131(5) -0.0003(4) 0.0023(4) -0.0014(4)
C4 0.0097(5) 0.0135(5) 0.0149(5) -0.0045(4) 0.0020(4) -0.0011(4)
C5 0.0116(5) 0.0132(5) 0.0177(5) -0.0005(4) -0.0005(4) 0.0023(4)
C6 0.0142(5) 0.0118(5) 0.0161(5) 0.0009(4) 0.0027(4) 0.0003(4)
C7 0.0110(5) 0.0177(5) 0.0261(6) 0.0012(5) -0.0026(4) -0.0012(4)
C8 0.0097(5) 0.0150(5) 0.0321(6) -0.0056(5) 0.0000(4) 0.0003(4)
Cl2 0.01022(12) 0.02307(15) 0.02365(14) -0.01029(11) 0.00091(10) -0.00122(10)
O4 0.0090(3) 0.0135(4) 0.0200(4) -0.0008(3) 0.0025(3) 0.0025(3)
O5 0.0076(3) 0.0166(4) 0.0209(4) -0.0024(3) 0.0015(3) 0.0009(3)
O6 0.0120(4) 0.0157(4) 0.0352(5) 0.0076(3) 0.0093(3) 0.0038(3)
C9 0.0099(5) 0.0136(5) 0.0134(5) 0.0030(4) 0.0028(4) 0.0019(4)
C10 0.0097(5) 0.0149(5) 0.0129(5) -0.0001(4) 0.0004(4) -0.0018(4)
C11 0.0121(5) 0.0128(5) 0.0139(5) -0.0004(4) 0.0019(4) 0.0020(4)
C12 0.0088(5) 0.0141(5) 0.0148(5) 0.0029(4) 0.0024(4) 0.0019(4)
C13 0.0115(5) 0.0126(5) 0.0179(5) 0.0006(4) 0.0016(4) -0.0016(4)
C14 0.0134(5) 0.0108(5) 0.0178(5) 0.0001(4) 0.0032(4) 0.0007(4)
C15 0.0102(5) 0.0152(5) 0.0200(5) 0.0000(4) -0.0009(4) 0.0006(4)
C16 0.0098(5) 0.0146(5) 0.0229(5) 0.0044(4) 0.0019(4) -0.0002(4)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.7372(11) . ?
O1 C1 1.3674(12) . ?
O1 H1O 0.838(9) . ?
O2 C4 1.3769(13) . ?
O2 C7 1.4282(13) . ?
O3 C8 1.4307(14) . ?
O3 H3O 0.829(9) . ?
C1 C6 1.3887(15) . ?
C1 C2 1.3940(15) . ?
C2 C3 1.3848(14) . ?
C3 C4 1.3936(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3930(15) . ?
C5 C6 1.3963(15) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.5061(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
Cl2 C10 1.7389(11) . ?
O4 C9 1.3699(12) . ?
O4 H4O 0.840(9) . ?
O5 C12 1.3770(12) . ?
O5 C15 1.4298(13) . ?
O6 C16 1.4260(13) . ?
O6 H6O 0.823(9) . ?
C9 C14 1.3871(15) . ?
C9 C10 1.3933(15) . ?
C10 C11 1.3869(14) . ?
C11 C12 1.3929(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.3928(15) . ?
C13 C14 1.3954(15) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.5053(15) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1O 111.8(10) . . ?
C4 O2 C7 117.30(9) . . ?
C8 O3 H3O 111.1(11) . . ?
O1 C1 C6 123.48(10) . . ?
O1 C1 C2 118.38(9) . . ?
C6 C1 C2 118.13(10) . . ?
C3 C2 C1 121.86(10) . . ?
C3 C2 Cl1 119.46(8) . . ?
C1 C2 Cl1 118.67(8) . . ?
C2 C3 C4 119.37(10) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
O2 C4 C5 125.03(10) . . ?
O2 C4 C3 115.17(9) . . ?
C5 C4 C3 119.78(10) . . ?
C4 C5 C6 119.87(10) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 120.96(10) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
O2 C7 C8 107.73(10) . . ?
O2 C7 H7A 110.2 . . ?
C8 C7 H7A 110.2 . . ?
O2 C7 H7B 110.2 . . ?
C8 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
O3 C8 C7 109.93(9) . . ?
O3 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
O3 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C9 O4 H4O 112.1(10) . . ?
C12 O5 C15 117.23(8) . . ?
C16 O6 H6O 110.6(12) . . ?
O4 C9 C14 123.52(10) . . ?
O4 C9 C10 118.41(9) . . ?
C14 C9 C10 118.07(10) . . ?
C11 C10 C9 121.83(10) . . ?
C11 C10 Cl2 119.23(8) . . ?
C9 C10 Cl2 118.93(8) . . ?
C10 C11 C12 119.26(10) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
O5 C12 C13 125.03(10) . . ?
O5 C12 C11 115.03(9) . . ?
C13 C12 C11 119.93(10) . . ?
C12 C13 C14 119.65(10) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C9 C14 C13 121.19(10) . . ?
C9 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
O5 C15 C16 107.82(9) . . ?
O5 C15 H15A 110.1 . . ?
C16 C15 H15A 110.1 . . ?
O5 C15 H15B 110.1 . . ?
C16 C15 H15B 110.1 . . ?
H15A C15 H15B 108.5 . . ?
O6 C16 C15 110.28(9) . . ?
O6 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
O6 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O O3 0.838(9) 1.822(9) 2.6413(12) 165.5(14) 2_655
O6 H6O O1 0.823(9) 2.016(10) 2.8076(11) 161.2(16) .
O4 H4O O6 0.840(9) 1.857(9) 2.6716(12) 163.2(14) 2_745
O3 H3O O4 0.829(9) 2.079(10) 2.8630(11) 157.7(16) 1_455

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 971456'
