# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelxl
#TrackingRef 'Dr.T.Mohandas.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 O3'
_chemical_formula_weight         216.19

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   4.5734(4)
_cell_length_b                   17.8195(13)
_cell_length_c                   13.2690(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.727(4)
_cell_angle_gamma                90.00
_cell_volume                     1080.88(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3855
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      29.8

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9108
_exptl_absorpt_correction_T_max  0.9804
_exptl_absorpt_process_details   'SADABS (Bruker 1999)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15476
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         31.81
_reflns_number_total             3680
_reflns_number_gt                2354
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'PLATON (Spek, 2003)'

_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)+(0.1031P)²+0.1368P] 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         3680
_refine_ls_number_parameters     153
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1673
_refine_ls_wR_factor_gt          0.1357
_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
C1 C 0.1292(2) 0.25010(6) 0.66318(8) 0.0378(2) Uani 1 1 d . . .
C2 C 0.2727(3) 0.31653(6) 0.63660(8) 0.0401(3) Uani 1 1 d . . .
C3 C 0.4722(3) 0.34857(7) 0.70245(9) 0.0427(3) Uani 1 1 d . . .
H3 H 0.5696 0.3922 0.6846 0.051 Uiso 1 1 calc R . .
C4 C 0.5292(3) 0.31565(7) 0.79655(9) 0.0414(3) Uani 1 1 d . . .
C5 C 0.3845(3) 0.25136(7) 0.82315(9) 0.0435(3) Uani 1 1 d . . .
H5 H 0.4212 0.2300 0.8862 0.052 Uiso 1 1 calc R . .
C6 C 0.1843(3) 0.21815(6) 0.75672(9) 0.0419(3) Uani 1 1 d . . .
H6 H 0.0874 0.1746 0.7750 0.050 Uiso 1 1 calc R . .
C7 C -0.1982(3) 0.15261(7) 0.60952(11) 0.0510(3) Uani 1 1 d . . .
H7A H -0.3514 0.1446 0.5585 0.061 Uiso 1 1 calc R . .
H7B H -0.2895 0.1549 0.6745 0.061 Uiso 1 1 calc R . .
C8 C 0.0025(3) 0.08939(7) 0.60897(10) 0.0484(3) Uani 1 1 d . . .
C9 C 0.1580(4) 0.03754(9) 0.60650(12) 0.0628(4) Uani 1 1 d . . .
C11 C 0.3518(4) 0.40742(8) 0.51136(11) 0.0613(4) Uani 1 1 d . . .
H11A H 0.5561 0.3948 0.5033 0.074 Uiso 1 1 calc R . .
H11B H 0.3406 0.4467 0.5617 0.074 Uiso 1 1 calc R . .
C12 C 0.2243(4) 0.43350(8) 0.41612(11) 0.0626(4) Uani 1 1 d . . .
C13 C 0.1315(5) 0.45850(10) 0.34048(14) 0.0828(6) Uani 1 1 d . . .
C14 C 0.7482(3) 0.34832(8) 0.86589(10) 0.0508(3) Uani 1 1 d . . .
H14 H 0.7805 0.3243 0.9275 0.061 Uiso 1 1 calc R . .
O1 O -0.05812(19) 0.22272(5) 0.59081(7) 0.0466(2) Uani 1 1 d . . .
O2 O 0.1968(2) 0.34364(5) 0.54282(7) 0.0555(3) Uani 1 1 d . . .
O3 O 0.8901(2) 0.40360(6) 0.85004(9) 0.0644(3) Uani 1 1 d . . .
H9 H 0.282(4) -0.0053(12) 0.6048(14) 0.081(6) Uiso 1 1 d . . .
H13 H 0.058(6) 0.4804(15) 0.280(2) 0.123(8) Uiso 1 1 d . . .

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
C1 0.0368(5) 0.0363(5) 0.0401(6) -0.0030(4) -0.0020(4) 0.0030(4)
C2 0.0452(6) 0.0377(6) 0.0370(5) 0.0027(4) -0.0035(4) 0.0006(5)
C3 0.0445(6) 0.0399(6) 0.0435(6) -0.0001(5) -0.0027(5) -0.0034(5)
C4 0.0399(6) 0.0446(6) 0.0394(6) -0.0046(5) -0.0026(4) 0.0040(5)
C5 0.0478(6) 0.0456(6) 0.0371(6) 0.0019(4) -0.0014(5) 0.0056(5)
C6 0.0458(6) 0.0370(6) 0.0430(6) 0.0027(4) 0.0016(5) 0.0006(5)
C7 0.0408(6) 0.0487(7) 0.0629(8) 0.0010(6) -0.0052(6) -0.0090(5)
C8 0.0541(7) 0.0418(6) 0.0487(7) -0.0040(5) -0.0074(5) -0.0109(5)
C9 0.0771(10) 0.0460(8) 0.0644(9) -0.0113(6) -0.0138(8) 0.0035(7)
C11 0.0796(10) 0.0521(8) 0.0513(8) 0.0123(6) -0.0105(7) -0.0180(7)
C12 0.0922(12) 0.0474(7) 0.0476(8) 0.0055(6) -0.0057(7) -0.0129(8)
C13 0.1330(18) 0.0621(10) 0.0519(9) 0.0076(7) -0.0201(10) -0.0039(11)
C14 0.0488(7) 0.0571(8) 0.0459(7) -0.0090(6) -0.0055(5) 0.0016(6)
O1 0.0501(5) 0.0402(4) 0.0487(5) 0.0017(3) -0.0116(4) -0.0052(4)
O2 0.0718(6) 0.0497(5) 0.0440(5) 0.0117(4) -0.0165(4) -0.0182(5)
O3 0.0604(6) 0.0611(6) 0.0711(7) -0.0147(5) -0.0077(5) -0.0107(5)

_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 1.3581(13) . ?
C1 C6 1.3817(16) . ?
C1 C2 1.4038(16) . ?
C2 C3 1.3688(16) . ?
C2 O2 1.3697(13) . ?
C3 C4 1.3969(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.3746(18) . ?
C4 C14 1.4603(17) . ?
C5 C6 1.3845(17) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.4290(15) . ?
C7 C8 1.453(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.167(2) . ?
C9 H9 0.95(2) . ?
C11 O2 1.4092(16) . ?
C11 C12 1.452(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.166(2) . ?
C13 H13 0.94(3) . ?
C14 O3 1.2016(17) . ?
C14 H14 0.9300 . ?

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 125.53(11) . . ?
O1 C1 C2 114.52(10) . . ?
C6 C1 C2 119.95(10) . . ?
C3 C2 O2 125.35(11) . . ?
C3 C2 C1 119.93(10) . . ?
O2 C2 C1 114.71(10) . . ?
C2 C3 C4 119.89(11) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.07(11) . . ?
C5 C4 C14 119.80(11) . . ?
C3 C4 C14 120.12(12) . . ?
C4 C5 C6 120.48(11) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.66(11) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
O1 C7 C8 112.98(11) . . ?
O1 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
O1 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 177.97(14) . . ?
C8 C9 H9 179.0(13) . . ?
O2 C11 C12 108.88(12) . . ?
O2 C11 H11A 109.9 . . ?
C12 C11 H11A 109.9 . . ?
O2 C11 H11B 109.9 . . ?
C12 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C13 C12 C11 175.81(17) . . ?
C12 C13 H13 178.0(17) . . ?
O3 C14 C4 125.46(13) . . ?
O3 C14 H14 117.3 . . ?
C4 C14 H14 117.3 . . ?
C1 O1 C7 117.89(10) . . ?
C2 O2 C11 115.95(10) . . ?

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 -178.45(11) . . . . ?
C6 C1 C2 C3 1.55(18) . . . . ?
O1 C1 C2 O2 1.11(15) . . . . ?
C6 C1 C2 O2 -178.89(10) . . . . ?
O2 C2 C3 C4 179.55(11) . . . . ?
C1 C2 C3 C4 -0.94(19) . . . . ?
C2 C3 C4 C5 -0.25(19) . . . . ?
C2 C3 C4 C14 178.16(11) . . . . ?
C3 C4 C5 C6 0.85(18) . . . . ?
C14 C4 C5 C6 -177.57(11) . . . . ?
O1 C1 C6 C5 179.04(10) . . . . ?
C2 C1 C6 C5 -0.96(18) . . . . ?
C4 C5 C6 C1 -0.24(18) . . . . ?
O1 C7 C8 C9 -129(5) . . . . ?
O2 C11 C12 C13 166(3) . . . . ?
C5 C4 C14 O3 179.02(13) . . . . ?
C3 C4 C14 O3 0.6(2) . . . . ?
C6 C1 O1 C7 -4.04(17) . . . . ?
C2 C1 O1 C7 175.96(11) . . . . ?
C8 C7 O1 C1 -69.46(15) . . . . ?
C3 C2 O2 C11 3.7(2) . . . . ?
C1 C2 O2 C11 -175.88(12) . . . . ?
C12 C11 O2 C2 -173.92(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        31.81
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.036


_database_code_depnum_ccdc_archive 'CCDC 824908'
#######################################################################
#
#                 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_shelxl
#TrackingRef 'mohandas-crystal-data.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 O3'
_chemical_formula_weight         214.21

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   4.9212(6)
_cell_length_b                   16.858(2)
_cell_length_c                   13.4277(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.252(5)
_cell_angle_gamma                90.00
_cell_volume                     1102.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2171
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      22.13

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9130
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_process_details   'SADABS (Bruker 1999)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10580
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2036
_reflns_number_gt                1403
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'PLATON (Spek, 2003)'

_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)+(0.0630P)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         2036
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1207
_refine_ls_wR_factor_gt          0.1037
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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 0.9537(4) 0.20704(11) 0.19421(14) 0.0480(5) Uani 1 1 d . . .
H1 H 1.0508 0.2543 0.1939 0.058 Uiso 1 1 calc R . .
C2 C 0.7902(3) 0.19441(9) 0.27492(12) 0.0379(4) Uani 1 1 d . . .
C3 C 0.7850(3) 0.25052(9) 0.35274(12) 0.0376(4) Uani 1 1 d . . .
C4 C 0.6244(3) 0.23770(10) 0.42756(13) 0.0414(4) Uani 1 1 d . . .
H4 H 0.6207 0.2749 0.4785 0.050 Uiso 1 1 calc R . .
C5 C 0.4687(3) 0.16896(10) 0.42622(13) 0.0408(4) Uani 1 1 d . . .
C6 C 0.4721(3) 0.11243(10) 0.35101(13) 0.0460(4) Uani 1 1 d . . .
H6 H 0.3684 0.0663 0.3506 0.055 Uiso 1 1 calc R . .
C7 C 0.6331(3) 0.12666(10) 0.27708(13) 0.0445(4) Uani 1 1 d . . .
H7 H 0.6362 0.0891 0.2265 0.053 Uiso 1 1 calc R . .
C8 C 0.9546(3) 0.37138(10) 0.42919(14) 0.0472(5) Uani 1 1 d . . .
H8A H 1.0266 0.3465 0.4927 0.057 Uiso 1 1 calc R . .
H8B H 0.7711 0.3907 0.4336 0.057 Uiso 1 1 calc R . .
C9 C 1.1315(3) 0.43693(10) 0.40814(13) 0.0462(5) Uani 1 1 d . . .
C10 C 1.2720(4) 0.49036(11) 0.39427(14) 0.0556(5) Uani 1 1 d . . .
H10 H 1.3840 0.5329 0.3832 0.067 Uiso 1 1 calc R . .
C11 C 0.1691(3) 0.09192(11) 0.51143(14) 0.0526(5) Uani 1 1 d . . .
H11A H 0.2939 0.0471 0.5180 0.063 Uiso 1 1 calc R . .
H11B H 0.0357 0.0842 0.4516 0.063 Uiso 1 1 calc R . .
C12 C 0.0303(4) 0.09761(12) 0.59964(16) 0.0578(5) Uani 1 1 d . . .
C13 C -0.0852(5) 0.10025(14) 0.6693(2) 0.0817(7) Uani 1 1 d . . .
H13 H -0.1776 0.1024 0.7250 0.098 Uiso 1 1 calc R . .
O1 O 0.9714(3) 0.15980(7) 0.12718(9) 0.0572(4) Uani 1 1 d . . .
O2 O 0.9470(2) 0.31552(7) 0.34910(8) 0.0460(3) Uani 1 1 d . . .
O3 O 0.3173(2) 0.16352(7) 0.50320(9) 0.0521(4) Uani 1 1 d . . .

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
C1 0.0579(11) 0.0434(10) 0.0452(11) -0.0017(9) 0.0157(9) 0.0015(8)
C2 0.0417(9) 0.0368(9) 0.0358(10) -0.0016(7) 0.0074(7) 0.0012(7)
C3 0.0383(9) 0.0368(9) 0.0383(10) -0.0006(7) 0.0073(7) -0.0008(7)
C4 0.0431(9) 0.0441(10) 0.0387(10) -0.0079(8) 0.0116(7) -0.0025(7)
C5 0.0364(8) 0.0477(10) 0.0398(10) -0.0015(8) 0.0107(7) -0.0016(7)
C6 0.0444(9) 0.0450(10) 0.0493(11) -0.0050(9) 0.0094(8) -0.0097(7)
C7 0.0495(10) 0.0445(10) 0.0398(11) -0.0108(8) 0.0072(8) -0.0004(8)
C8 0.0532(10) 0.0449(10) 0.0457(11) -0.0107(8) 0.0146(8) -0.0083(8)
C9 0.0527(10) 0.0425(10) 0.0444(11) -0.0071(8) 0.0109(8) -0.0037(8)
C10 0.0658(12) 0.0492(11) 0.0534(13) -0.0039(9) 0.0138(9) -0.0112(9)
C11 0.0484(10) 0.0542(12) 0.0572(13) 0.0032(9) 0.0146(9) -0.0098(8)
C12 0.0589(12) 0.0597(13) 0.0573(14) 0.0083(10) 0.0171(10) -0.0101(9)
C13 0.1000(17) 0.0838(17) 0.0699(16) 0.0080(13) 0.0414(14) -0.0141(13)
O1 0.0815(9) 0.0508(8) 0.0439(8) -0.0053(6) 0.0241(7) 0.0077(6)
O2 0.0547(7) 0.0416(7) 0.0455(8) -0.0091(5) 0.0204(5) -0.0106(5)
O3 0.0525(7) 0.0559(8) 0.0527(8) -0.0070(6) 0.0235(6) -0.0154(6)

_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 1.214(2) . ?
C1 C2 1.455(2) . ?
C1 H1 0.9300 . ?
C2 C7 1.382(2) . ?
C2 C3 1.412(2) . ?
C3 O2 1.3602(18) . ?
C3 C4 1.381(2) . ?
C4 C5 1.388(2) . ?
C4 H4 0.9300 . ?
C5 O3 1.3615(19) . ?
C5 C6 1.390(2) . ?
C6 C7 1.377(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O2 1.426(2) . ?
C8 C9 1.459(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.167(2) . ?
C10 H10 0.9300 . ?
C11 O3 1.423(2) . ?
C11 C12 1.453(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.163(3) . ?
C13 H13 0.9300 . ?

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 C2 124.23(17) . . ?
O1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C7 C2 C3 117.92(14) . . ?
C7 C2 C1 120.48(15) . . ?
C3 C2 C1 121.59(15) . . ?
O2 C3 C4 123.48(14) . . ?
O2 C3 C2 116.09(13) . . ?
C4 C3 C2 120.42(14) . . ?
C3 C4 C5 119.57(15) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
O3 C5 C4 114.07(14) . . ?
O3 C5 C6 124.76(14) . . ?
C4 C5 C6 121.17(15) . . ?
C7 C6 C5 118.18(15) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C6 C7 C2 122.72(15) . . ?
C6 C7 H7 118.6 . . ?
C2 C7 H7 118.6 . . ?
O2 C8 C9 107.81(13) . . ?
O2 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
O2 C8 H8B 110.1 . . ?
C9 C8 H8B 110.1 . . ?
H8A C8 H8B 108.5 . . ?
C10 C9 C8 177.84(19) . . ?
C9 C10 H10 180.0 . . ?
O3 C11 C12 108.27(15) . . ?
O3 C11 H11A 110.0 . . ?
C12 C11 H11A 110.0 . . ?
O3 C11 H11B 110.0 . . ?
C12 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
C13 C12 C11 178.0(2) . . ?
C12 C13 H13 180.0 . . ?
C3 O2 C8 117.19(12) . . ?
C5 O3 C11 117.31(13) . . ?

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 C7 -2.5(3) . . . . ?
O1 C1 C2 C3 177.85(16) . . . . ?
C7 C2 C3 O2 178.61(13) . . . . ?
C1 C2 C3 O2 -1.8(2) . . . . ?
C7 C2 C3 C4 -0.7(2) . . . . ?
C1 C2 C3 C4 178.91(15) . . . . ?
O2 C3 C4 C5 -178.92(14) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C4 C5 O3 -179.36(14) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
O3 C5 C6 C7 179.12(15) . . . . ?
C4 C5 C6 C7 -0.5(2) . . . . ?
C5 C6 C7 C2 0.1(2) . . . . ?
C3 C2 C7 C6 0.5(2) . . . . ?
C1 C2 C7 C6 -179.10(16) . . . . ?
O2 C8 C9 C10 -175(5) . . . . ?
O3 C11 C12 C13 167(7) . . . . ?
C4 C3 O2 C8 1.9(2) . . . . ?
C2 C3 O2 C8 -177.34(14) . . . . ?
C9 C8 O2 C3 -178.00(13) . . . . ?
C4 C5 O3 C11 -175.19(15) . . . . ?
C6 C5 O3 C11 5.2(2) . . . . ?
C12 C11 O3 C5 178.15(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.041


_database_code_depnum_ccdc_archive 'CCDC 841652'
