# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_ftg
_database_code_depnum_ccdc_archive 'CCDC 1027730'
_audit_update_record             
;
2014-10-06 deposited with the CCDC.
2018-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
'(1E)-1-(3,5-diacetyl-2,4-dihydroxy-6-oxocyclohexa-2,4-dien-1-yl)
 -N-methylethaniminium (2)'
 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H15 N O5 '
_chemical_formula_sum            'C13 H15 N O5 '
_chemical_formula_weight         265.26

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   17.6428(7)
_cell_length_b                   7.0164(3)
_cell_length_c                   19.1027(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2364.70(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1511
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      28.67

_exptl_crystal_description       nedlle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.567
_exptl_absorpt_correction_T_max  0.678
_exptl_absorpt_process_details   'CrysAis, oxford Diffraction'

_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  KM4-CCD
_diffrn_measurement_method       /w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11591
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_sigmaI/netI    0.0750
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.14
_diffrn_reflns_theta_max         28.67
_reflns_number_total             2870
_reflns_number_gt                1511
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0488P)²+0.0000P] 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         2870
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.0983
_refine_ls_goodness_of_fit_ref   0.900
_refine_ls_restrained_S_all      0.900
_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
O1 O -0.36581(7) 0.09179(19) -0.25888(7) 0.0239(4) Uani 1 1 d . . .
O2 O -0.21386(7) 0.2348(2) -0.45630(7) 0.0244(4) Uani 1 1 d . . .
H2O H -0.1575 0.2427 -0.4642 0.037 Uiso 1 1 d R . .
O3 O -0.09950(7) 0.05192(19) -0.24320(7) 0.0264(4) Uani 1 1 d . . .
H3O H -0.1218 0.0043 -0.1950 0.040 Uiso 1 1 d R . .
O4 O -0.07661(8) 0.2467(2) -0.44482(8) 0.0289(4) Uani 1 1 d . . .
O5 O -0.17512(7) -0.04668(19) -0.14464(7) 0.0257(4) Uani 1 1 d . . .
N1 N -0.42780(9) 0.1851(2) -0.37131(9) 0.0213(4) Uani 1 1 d . . .
H1N H -0.4209 0.1560 -0.3224 0.026 Uiso 1 1 d R . .
C1 C -0.30159(10) 0.1037(3) -0.28816(11) 0.0185(5) Uani 1 1 d . . .
C2 C -0.23345(10) 0.0610(3) -0.24800(11) 0.0173(4) Uani 1 1 d . . .
C3 C -0.16127(11) 0.0898(3) -0.27950(11) 0.0195(5) Uani 1 1 d . . .
C4 C -0.15342(11) 0.1563(3) -0.34940(11) 0.0186(5) Uani 1 1 d . . .
C5 C -0.22094(10) 0.1820(3) -0.39012(11) 0.0182(5) Uani 1 1 d . . .
C6 C -0.29455(11) 0.1576(3) -0.36144(11) 0.0173(5) Uani 1 1 d . . .
C7 C -0.36214(11) 0.1895(3) -0.40315(11) 0.0197(5) Uani 1 1 d . . .
C8 C -0.36157(11) 0.2244(3) -0.48067(11) 0.0293(5) Uani 1 1 d . . .
H8A H -0.4136 0.2210 -0.4985 0.044 Uiso 1 1 calc R . .
H8B H -0.3314 0.1255 -0.5038 0.044 Uiso 1 1 calc R . .
H8C H -0.3393 0.3497 -0.4902 0.044 Uiso 1 1 calc R . .
C9 C -0.50204(11) 0.2106(3) -0.40428(12) 0.0337(6) Uani 1 1 d . . .
H9A H -0.5023 0.3296 -0.4311 0.051 Uiso 1 1 calc R . .
H9B H -0.5413 0.2161 -0.3680 0.051 Uiso 1 1 calc R . .
H9C H -0.5122 0.1032 -0.4357 0.051 Uiso 1 1 calc R . .
C10 C -0.23634(11) -0.0101(3) -0.17701(11) 0.0198(5) Uani 1 1 d . . .
C11 C -0.30785(11) -0.0419(3) -0.13704(11) 0.0232(5) Uani 1 1 d . . .
H11A H -0.3321 0.0809 -0.1275 0.035 Uiso 1 1 calc R . .
H11B H -0.2962 -0.1058 -0.0927 0.035 Uiso 1 1 calc R . .
H11C H -0.3422 -0.1219 -0.1646 0.035 Uiso 1 1 calc R . .
C12 C -0.08059(11) 0.2024(3) -0.38055(12) 0.0219(5) Uani 1 1 d . . .
C13 C -0.00803(11) 0.2084(3) -0.34008(12) 0.0289(5) Uani 1 1 d . . .
H13A H 0.0052 0.0794 -0.3246 0.043 Uiso 1 1 calc R . .
H13B H -0.0142 0.2911 -0.2992 0.043 Uiso 1 1 calc R . .
H13C H 0.0325 0.2585 -0.3700 0.043 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.266(2) . ?
O2 C5 1.323(2) . ?
O2 H2O 1.0080 . ?
O3 C3 1.319(2) . ?
O3 H3O 1.0553 . ?
O4 C12 1.268(2) . ?
O4 H2O 1.4741 . ?
O5 C10 1.271(2) . ?
O5 H3O 1.3924 . ?
N1 C7 1.309(2) . ?
N1 C9 1.464(2) . ?
N1 H1N 0.9636 . ?
C1 C6 1.455(3) . ?
C1 C2 1.457(3) . ?
C2 C3 1.423(3) . ?
C2 C10 1.446(3) . ?
C3 C4 1.421(3) . ?
C4 C5 1.434(3) . ?
C4 C12 1.453(3) . ?
C5 C6 1.420(3) . ?
C6 C7 1.452(3) . ?
C7 C8 1.501(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.491(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.496(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
C5 O2 H2O 104.6 . . ?
C3 O3 H3O 102.4 . . ?
C12 O4 H2O 100.7 . . ?
C10 O5 H3O 100.7 . . ?
C7 N1 C9 126.09(18) . . ?
C7 N1 H1N 110.1 . . ?
C9 N1 H1N 123.8 . . ?
O1 C1 C6 121.22(17) . . ?
O1 C1 C2 119.47(18) . . ?
C6 C1 C2 119.30(17) . . ?
C3 C2 C10 118.51(17) . . ?
C3 C2 C1 119.11(18) . . ?
C10 C2 C1 122.39(17) . . ?
O3 C3 C4 118.67(17) . . ?
O3 C3 C2 119.25(18) . . ?
C4 C3 C2 122.08(18) . . ?
C3 C4 C5 118.03(17) . . ?
C3 C4 C12 122.97(18) . . ?
C5 C4 C12 118.99(18) . . ?
O2 C5 C6 119.27(17) . . ?
O2 C5 C4 118.36(17) . . ?
C6 C5 C4 122.36(19) . . ?
C5 C6 C7 121.39(18) . . ?
C5 C6 C1 118.73(17) . . ?
C7 C6 C1 119.86(17) . . ?
N1 C7 C6 117.93(18) . . ?
N1 C7 C8 117.93(17) . . ?
C6 C7 C8 124.13(17) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O5 C10 C2 119.74(17) . . ?
O5 C10 C11 116.07(18) . . ?
C2 C10 C11 124.18(18) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 C4 120.00(19) . . ?
O4 C12 C13 116.48(18) . . ?
C4 C12 C13 123.48(19) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -174.86(18) . . . . ?
C6 C1 C2 C3 5.7(3) . . . . ?
O1 C1 C2 C10 5.2(3) . . . . ?
C6 C1 C2 C10 -174.26(17) . . . . ?
C10 C2 C3 O3 -0.3(3) . . . . ?
C1 C2 C3 O3 179.74(17) . . . . ?
C10 C2 C3 C4 178.99(18) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
O3 C3 C4 C5 175.00(17) . . . . ?
C2 C3 C4 C5 -4.3(3) . . . . ?
O3 C3 C4 C12 -6.2(3) . . . . ?
C2 C3 C4 C12 174.49(18) . . . . ?
C3 C4 C5 O2 -176.68(17) . . . . ?
C12 C4 C5 O2 4.5(3) . . . . ?
C3 C4 C5 C6 4.9(3) . . . . ?
C12 C4 C5 C6 -173.88(17) . . . . ?
O2 C5 C6 C7 -0.1(3) . . . . ?
C4 C5 C6 C7 178.28(18) . . . . ?
O2 C5 C6 C1 -178.64(17) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
O1 C1 C6 C5 175.50(18) . . . . ?
C2 C1 C6 C5 -5.1(3) . . . . ?
O1 C1 C6 C7 -3.1(3) . . . . ?
C2 C1 C6 C7 176.34(17) . . . . ?
C9 N1 C7 C6 -178.92(18) . . . . ?
C9 N1 C7 C8 0.2(3) . . . . ?
C5 C6 C7 N1 -172.50(17) . . . . ?
C1 C6 C7 N1 6.0(3) . . . . ?
C5 C6 C7 C8 8.4(3) . . . . ?
C1 C6 C7 C8 -173.06(18) . . . . ?
C3 C2 C10 O5 -0.6(3) . . . . ?
C1 C2 C10 O5 179.34(18) . . . . ?
C3 C2 C10 C11 178.32(18) . . . . ?
C1 C2 C10 C11 -1.7(3) . . . . ?
C3 C4 C12 O4 174.42(19) . . . . ?
C5 C4 C12 O4 -6.8(3) . . . . ?
C3 C4 C12 C13 -8.0(3) . . . . ?
C5 C4 C12 C13 170.79(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.942
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.059

_vrf_PLAT772_I                   
;
PROBLEM: Suspect O-H Bond in CIF:   O4     --  H2O     ..       1.47 Ang. 
RESPONSE: this distance is probably possible
taht in this molecule we observe interactions
beetwen H and O atoms leading to this that 
hydrogen it will will be in the middle
;
# end Validation Reply Form



####################################################################### 
# 
# 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_bf5th
_database_code_depnum_ccdc_archive 'CCDC 1027731'
_audit_update_record             
;
2014-10-06 deposited with the CCDC.
2018-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
'1,1',1'-(2,4,6-trihydroxybenzene-1,3,5-triyl)triethanone'  
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 O6'
_chemical_formula_sum            'C12 H12 O6'
_chemical_formula_weight         252.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   9.298(3)
_cell_length_b                   16.631(4)
_cell_length_c                   7.232(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.90(4)
_cell_angle_gamma                90.00
_cell_volume                     1070.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2111
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      26.07

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_process_details   'CrysAlis, Oxford Diffraction'

_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  KM4-CCD
_diffrn_measurement_method       /w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11575
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         26.07
_reflns_number_total             2111
_reflns_number_gt                1543
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0624P)²+0.0000P] 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         2111
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_restrained_S_all      0.949
_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
C1 C 0.77138(15) 0.25000(8) 0.53390(19) 0.0148(3) Uani 1 1 d . . .
O1 O 0.90620(11) 0.25363(5) 0.66101(14) 0.0191(3) Uani 1 1 d . . .
H1 H 0.9308 0.1916 0.6858 0.029 Uiso 1 1 d R . .
C2 C 0.70601(15) 0.17333(8) 0.47357(19) 0.0152(3) Uani 1 1 d . . .
C3 C 0.56003(15) 0.17104(8) 0.33913(19) 0.0154(3) Uani 1 1 d . . .
C4 C 0.47809(15) 0.24251(8) 0.27038(19) 0.0156(3) Uani 1 1 d . . .
C5 C 0.54808(15) 0.31755(8) 0.33390(19) 0.0155(3) Uani 1 1 d . . .
C6 C 0.69675(15) 0.32252(8) 0.46290(19) 0.0151(3) Uani 1 1 d . . .
O2 O 0.49999(10) 0.10043(6) 0.27791(14) 0.0194(2) Uani 1 1 d . . .
H2 H 0.4032 0.1144 0.1832 0.029 Uiso 1 1 d R . .
O3 O 0.47406(10) 0.38437(6) 0.26920(14) 0.0215(3) Uani 1 1 d . . .
H3 H 0.5569 0.4283 0.3411 0.032 Uiso 1 1 d R . .
C7 C 0.79155(15) 0.10114(9) 0.55210(19) 0.0175(3) Uani 1 1 d . . .
C8 C 0.73796(17) 0.01762(9) 0.4976(2) 0.0259(4) Uani 1 1 d . . .
H8A H 0.7179 0.0106 0.3579 0.039 Uiso 1 1 calc R . .
H8B H 0.6454 0.0081 0.5332 0.039 Uiso 1 1 calc R . .
H8C H 0.8152 -0.0207 0.5659 0.039 Uiso 1 1 calc R . .
O4 O 0.91940(11) 0.10839(6) 0.67254(14) 0.0216(3) Uani 1 1 d . . .
C9 C 0.32603(15) 0.23544(8) 0.13555(19) 0.0167(3) Uani 1 1 d . . .
C10 C 0.22689(15) 0.30596(9) 0.0609(2) 0.0210(3) Uani 1 1 d . . .
H10A H 0.2745 0.3408 -0.0134 0.031 Uiso 1 1 calc R . .
H10B H 0.2112 0.3362 0.1698 0.031 Uiso 1 1 calc R . .
H10C H 0.1298 0.2871 -0.0225 0.031 Uiso 1 1 calc R . .
O5 O 0.27457(11) 0.16723(6) 0.08030(14) 0.0217(3) Uani 1 1 d . . .
C11 C 0.76374(16) 0.40250(8) 0.51373(19) 0.0178(3) Uani 1 1 d . . .
C12 C 0.92203(15) 0.41585(9) 0.6356(2) 0.0210(3) Uani 1 1 d . . .
H12A H 0.9354 0.3929 0.7643 0.031 Uiso 1 1 calc R . .
H12B H 0.9430 0.4737 0.6472 0.031 Uiso 1 1 calc R . .
H12C H 0.9914 0.3897 0.5751 0.031 Uiso 1 1 calc R . .
O6 O 0.68694(11) 0.46387(6) 0.45005(14) 0.0246(3) 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
C1 O1 1.3229(17) . ?
C1 C6 1.4116(19) . ?
C1 C2 1.4254(18) . ?
O1 H1 1.0605 . ?
C2 C3 1.4219(19) . ?
C2 C7 1.4608(19) . ?
C3 O2 1.3202(16) . ?
C3 C4 1.4215(19) . ?
C4 C5 1.4206(19) . ?
C4 C9 1.470(2) . ?
C5 O3 1.3192(16) . ?
C5 C6 1.4277(19) . ?
C6 C11 1.4694(19) . ?
O2 H2 0.9870 . ?
O3 H3 1.0793 . ?
C7 O4 1.2587(17) . ?
C7 C8 1.489(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O4 H1 1.3893 . ?
C9 O5 1.2507(16) . ?
C9 C10 1.4923(19) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O6 1.2540(17) . ?
C11 C12 1.4960(19) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
O6 H3 1.3706 . ?

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
O1 C1 C6 118.69(12) . . ?
O1 C1 C2 119.15(11) . . ?
C6 C1 C2 122.16(12) . . ?
C1 O1 H1 100.8 . . ?
C3 C2 C1 118.08(12) . . ?
C3 C2 C7 123.19(12) . . ?
C1 C2 C7 118.74(12) . . ?
O2 C3 C4 119.68(12) . . ?
O2 C3 C2 118.67(12) . . ?
C4 C3 C2 121.65(12) . . ?
C5 C4 C3 118.23(12) . . ?
C5 C4 C9 123.13(12) . . ?
C3 C4 C9 118.64(12) . . ?
O3 C5 C4 118.85(12) . . ?
O3 C5 C6 119.29(12) . . ?
C4 C5 C6 121.85(12) . . ?
C1 C6 C5 117.93(12) . . ?
C1 C6 C11 123.68(12) . . ?
C5 C6 C11 118.39(12) . . ?
C3 O2 H2 103.6 . . ?
C5 O3 H3 100.0 . . ?
O4 C7 C2 119.22(12) . . ?
O4 C7 C8 116.65(12) . . ?
C2 C7 C8 124.13(12) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 O4 H1 100.4 . . ?
O5 C9 C4 119.29(12) . . ?
O5 C9 C10 117.29(12) . . ?
C4 C9 C10 123.42(12) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O6 C11 C6 119.35(12) . . ?
O6 C11 C12 116.95(12) . . ?
C6 C11 C12 123.69(12) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 O6 H3 100.0 . . ?

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
O1 C1 C2 C3 179.04(12) . . . . ?
C6 C1 C2 C3 -0.8(2) . . . . ?
O1 C1 C2 C7 -1.0(2) . . . . ?
C6 C1 C2 C7 179.20(12) . . . . ?
C1 C2 C3 O2 178.10(12) . . . . ?
C7 C2 C3 O2 -1.9(2) . . . . ?
C1 C2 C3 C4 -2.1(2) . . . . ?
C7 C2 C3 C4 177.98(13) . . . . ?
O2 C3 C4 C5 -177.82(12) . . . . ?
C2 C3 C4 C5 2.4(2) . . . . ?
O2 C3 C4 C9 1.5(2) . . . . ?
C2 C3 C4 C9 -178.34(13) . . . . ?
C3 C4 C5 O3 179.11(12) . . . . ?
C9 C4 C5 O3 -0.2(2) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C9 C4 C5 C6 -179.12(13) . . . . ?
O1 C1 C6 C5 -176.67(12) . . . . ?
C2 C1 C6 C5 3.1(2) . . . . ?
O1 C1 C6 C11 3.6(2) . . . . ?
C2 C1 C6 C11 -176.62(13) . . . . ?
O3 C5 C6 C1 178.23(12) . . . . ?
C4 C5 C6 C1 -2.8(2) . . . . ?
O3 C5 C6 C11 -2.0(2) . . . . ?
C4 C5 C6 C11 176.94(12) . . . . ?
C3 C2 C7 O4 -179.08(13) . . . . ?
C1 C2 C7 O4 1.0(2) . . . . ?
C3 C2 C7 C8 1.5(2) . . . . ?
C1 C2 C7 C8 -178.47(13) . . . . ?
C5 C4 C9 O5 177.09(13) . . . . ?
C3 C4 C9 O5 -2.2(2) . . . . ?
C5 C4 C9 C10 -3.6(2) . . . . ?
C3 C4 C9 C10 177.11(13) . . . . ?
C1 C6 C11 O6 -177.11(13) . . . . ?
C5 C6 C11 O6 3.2(2) . . . . ?
C1 C6 C11 C12 4.3(2) . . . . ?
C5 C6 C11 C12 -175.45(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.049
#----------------------------------------
_publ                            requested
