# 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

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H8 O2'
_chemical_formula_weight         148.15

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   8.6255(4)
_cell_length_b                   6.6197(3)
_cell_length_c                   13.1658(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.297(4)
_cell_angle_gamma                90
_cell_volume                     751.73(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    1989
_cell_measurement_theta_min      3.0711
_cell_measurement_theta_max      29.1390

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.310
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93684
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_reflns_number            6402
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.445
_diffrn_reflns_theta_max         26.351
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             1528
_reflns_number_gt                1185
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²+0.0972P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.074(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1528
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1130
_refine_ls_wR_factor_gt          0.1031
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.61405(13) 0.78185(15) 0.75889(8) 0.0708(4) Uani 1 1 d . . . . .
O1 O 0.61857(14) 0.30094(16) 0.95402(8) 0.0770(4) Uani 1 1 d . . . . .
C3 C 0.52488(13) 0.44634(18) 0.80194(9) 0.0473(3) Uani 1 1 d . . . . .
C7 C 0.61869(15) 0.44348(19) 0.89567(10) 0.0529(4) Uani 1 1 d . . . . .
C4 C 0.53239(15) 0.6117(2) 0.73604(10) 0.0525(4) Uani 1 1 d . . . . .
C2 C 0.43532(16) 0.2806(2) 0.77248(12) 0.0622(4) Uani 1 1 d . . . . .
H2 H 0.4272 0.1699 0.8157 0.075 Uiso 1 1 calc R U . . .
C9 C 0.6438(2) 0.8101(2) 0.86552(12) 0.0721(5) Uani 1 1 d . . . . .
H9B H 0.5471 0.8381 0.9000 0.087 Uiso 1 1 calc R U . . .
H9A H 0.7117 0.9254 0.8750 0.087 Uiso 1 1 calc R U . . .
C5 C 0.45752(19) 0.6062(3) 0.64255(11) 0.0727(5) Uani 1 1 d . . . . .
H5 H 0.4654 0.7149 0.5982 0.087 Uiso 1 1 calc R U . . .
C1 C 0.35882(17) 0.2785(3) 0.68038(15) 0.0774(5) Uani 1 1 d . . . . .
H1 H 0.2984 0.1678 0.6620 0.093 Uiso 1 1 calc R U . . .
C8 C 0.71795(18) 0.6257(2) 0.91141(12) 0.0679(4) Uani 1 1 d . . . . .
H8B H 0.8184 0.6036 0.8805 0.081 Uiso 1 1 calc R U . . .
H8A H 0.7340 0.6472 0.9836 0.081 Uiso 1 1 calc R U . . .
C6 C 0.37208(18) 0.4403(3) 0.61586(13) 0.0803(5) Uani 1 1 d . . . . .
H6 H 0.3222 0.4371 0.5531 0.096 Uiso 1 1 calc R U . . .


_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
O2 C4 1.3612(16) . ?
O2 C9 1.4380(19) . ?
O1 C7 1.2168(16) . ?
C3 C2 1.3959(18) . ?
C3 C4 1.3986(18) . ?
C3 C7 1.4722(19) . ?
C7 C8 1.4931(19) . ?
C4 C5 1.388(2) . ?
C2 C1 1.377(2) . ?
C2 H2 0.9300 . ?
C9 C8 1.503(2) . ?
C9 H9B 0.9700 . ?
C9 H9A 0.9700 . ?
C5 C6 1.367(2) . ?
C5 H5 0.9300 . ?
C1 C6 1.372(3) . ?
C1 H1 0.9300 . ?
C8 H8B 0.9700 . ?
C8 H8A 0.9700 . ?
C6 H6 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
C4 O2 C9 114.39(10) . . ?
C2 C3 C4 118.06(13) . . ?
C2 C3 C7 121.59(12) . . ?
C4 C3 C7 120.20(12) . . ?
O1 C7 C3 122.48(13) . . ?
O1 C7 C8 122.77(14) . . ?
C3 C7 C8 114.72(11) . . ?
O2 C4 C5 117.13(13) . . ?
O2 C4 C3 122.42(12) . . ?
C5 C4 C3 120.44(14) . . ?
C1 C2 C3 120.96(15) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
O2 C9 C8 111.12(12) . . ?
O2 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
O2 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
H9B C9 H9A 108.0 . . ?
C6 C5 C4 119.81(15) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C6 C1 C2 119.73(15) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C7 C8 C9 110.97(12) . . ?
C7 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
H8B C8 H8A 108.0 . . ?
C5 C6 C1 120.95(15) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?

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
C2 C3 C7 O1 -2.9(2) . . . . ?
C4 C3 C7 O1 -178.28(13) . . . . ?
C2 C3 C7 C8 174.99(12) . . . . ?
C4 C3 C7 C8 -0.37(17) . . . . ?
C9 O2 C4 C5 159.89(14) . . . . ?
C9 O2 C4 C3 -21.24(19) . . . . ?
C2 C3 C4 O2 178.66(11) . . . . ?
C7 C3 C4 O2 -5.83(19) . . . . ?
C2 C3 C4 C5 -2.51(19) . . . . ?
C7 C3 C4 C5 173.01(12) . . . . ?
C4 C3 C2 C1 1.1(2) . . . . ?
C7 C3 C2 C1 -174.31(13) . . . . ?
C4 O2 C9 C8 52.84(17) . . . . ?
O2 C4 C5 C6 -179.18(13) . . . . ?
C3 C4 C5 C6 1.9(2) . . . . ?
C3 C2 C1 C6 0.8(2) . . . . ?
O1 C7 C8 C9 -151.19(14) . . . . ?
C3 C7 C8 C9 30.90(17) . . . . ?
O2 C9 C8 C7 -57.44(17) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C2 C1 C6 C5 -1.5(2) . . . . ?

_refine_diff_density_max         0.132
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.024

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 982620'
#######################################################################
#
#                 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

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H8 O2'
_chemical_formula_weight         196.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   4.8978(14)
_cell_length_b                   13.654(5)
_cell_length_c                   14.129(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     944.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    1016
_cell_measurement_theta_min      6.2599
_cell_measurement_theta_max      71.0518

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.754
_shelx_estimated_absorpt_T_min   0.773
_shelx_estimated_absorpt_T_max   0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76014
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_reflns_number            7057
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         6.265
_diffrn_reflns_theta_max         71.188
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1762
_reflns_number_gt                877
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.641
_reflns_Friedel_fraction_max     0.948
_reflns_Friedel_fraction_full    0.982

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0020P)²+2.2200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0059(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 223 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.0(7)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         1762
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1625
_refine_ls_R_factor_gt           0.1100
_refine_ls_wR_factor_ref         0.1900
_refine_ls_wR_factor_gt          0.1685
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5187(15) 0.9047(5) 0.9612(5) 0.104(2) Uani 1 1 d . . . . .
O2 O 0.6034(17) 1.0827(6) 0.7299(6) 0.127(3) Uani 1 1 d . . . . .
C1 C 0.397(2) 1.0523(7) 0.8781(8) 0.091(3) Uani 1 1 d . . . . .
C2 C 0.368(2) 0.9901(8) 0.9540(8) 0.095(3) Uani 1 1 d . . . . .
C3 C 0.745(2) 0.9419(9) 0.8133(8) 0.095(3) Uani 1 1 d . . . . .
C4 C 0.588(2) 1.0318(9) 0.8025(9) 0.103(3) Uani 1 1 d . . . . .
C5 C 0.241(3) 1.1380(9) 0.8780(10) 0.119(4) Uani 1 1 d . . . . .
H5 H 0.2639 1.1827 0.8289 0.142 Uiso 1 1 calc R U . . .
C6 C 0.183(3) 1.0070(10) 1.0270(8) 0.114(4) Uani 1 1 d . . . . .
H6 H 0.1606 0.9630 1.0766 0.137 Uiso 1 1 calc R U . . .
C7 C 0.707(2) 0.8822(8) 0.8919(9) 0.102(3) Uani 1 1 d . . . . .
C8 C 0.057(3) 1.1578(10) 0.9477(11) 0.126(5) Uani 1 1 d . . . . .
H8 H -0.0498 1.2140 0.9453 0.151 Uiso 1 1 calc R U . . .
C9 C 0.033(2) 1.0930(11) 1.0219(10) 0.117(4) Uani 1 1 d . . . . .
H9 H -0.0882 1.1075 1.0705 0.141 Uiso 1 1 calc R U . . .
C10 C 0.847(3) 0.7956(8) 0.9033(10) 0.123(5) Uani 1 1 d . . . . .
H10 H 0.8101 0.7547 0.9543 0.147 Uiso 1 1 calc R U . . .
C11 C 0.946(2) 0.9137(10) 0.7490(10) 0.116(4) Uani 1 1 d . . . . .
H11 H 0.9850 0.9541 0.6977 0.140 Uiso 1 1 calc R U . . .
C12 C 1.088(3) 0.8282(11) 0.7594(11) 0.125(4) Uani 1 1 d . . . . .
H12 H 1.2131 0.8090 0.7135 0.150 Uiso 1 1 calc R U . . .
C13 C 1.044(3) 0.7705(11) 0.8381(12) 0.138(5) Uani 1 1 d . . . . .
H13 H 1.1483 0.7143 0.8472 0.166 Uiso 1 1 calc R U . . .


_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 C7 1.379(12) . ?
O1 C2 1.384(12) . ?
O2 C4 1.241(12) . ?
C1 C2 1.376(13) . ?
C1 C5 1.397(14) . ?
C1 C4 1.448(15) . ?
C2 C6 1.392(14) . ?
C3 C7 1.390(14) . ?
C3 C11 1.396(15) . ?
C3 C4 1.455(14) . ?
C5 C8 1.363(16) . ?
C5 H5 0.9300 . ?
C6 C9 1.385(15) . ?
C6 H6 0.9300 . ?
C7 C10 1.378(14) . ?
C8 C9 1.377(16) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C13 1.376(17) . ?
C10 H10 0.9300 . ?
C11 C12 1.365(15) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(17) . ?
C12 H12 0.9300 . ?
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
C7 O1 C2 119.5(9) . . ?
C2 C1 C5 117.4(11) . . ?
C2 C1 C4 121.6(10) . . ?
C5 C1 C4 120.9(12) . . ?
C1 C2 O1 121.4(10) . . ?
C1 C2 C6 122.9(11) . . ?
O1 C2 C6 115.7(11) . . ?
C7 C3 C11 117.0(12) . . ?
C7 C3 C4 120.5(11) . . ?
C11 C3 C4 122.4(12) . . ?
O2 C4 C1 122.6(12) . . ?
O2 C4 C3 121.9(12) . . ?
C1 C4 C3 115.2(11) . . ?
C8 C5 C1 121.8(13) . . ?
C8 C5 H5 119.1 . . ?
C1 C5 H5 119.1 . . ?
C9 C6 C2 116.5(12) . . ?
C9 C6 H6 121.7 . . ?
C2 C6 H6 121.7 . . ?
C10 C7 O1 116.3(12) . . ?
C10 C7 C3 121.9(12) . . ?
O1 C7 C3 121.8(10) . . ?
C5 C8 C9 118.7(13) . . ?
C5 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C8 C9 C6 122.6(12) . . ?
C8 C9 H9 118.7 . . ?
C6 C9 H9 118.7 . . ?
C13 C10 C7 119.1(14) . . ?
C13 C10 H10 120.5 . . ?
C7 C10 H10 120.5 . . ?
C12 C11 C3 121.7(13) . . ?
C12 C11 H11 119.2 . . ?
C3 C11 H11 119.2 . . ?
C11 C12 C13 119.8(14) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C10 C13 C12 120.3(14) . . ?
C10 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 O1 -178.4(9) . . . . ?
C4 C1 C2 O1 -0.4(16) . . . . ?
C5 C1 C2 C6 3.0(16) . . . . ?
C4 C1 C2 C6 -179.0(10) . . . . ?
C7 O1 C2 C1 1.3(14) . . . . ?
C7 O1 C2 C6 180.0(9) . . . . ?
C2 C1 C4 O2 174.4(11) . . . . ?
C5 C1 C4 O2 -7.7(17) . . . . ?
C2 C1 C4 C3 -0.3(15) . . . . ?
C5 C1 C4 C3 177.7(10) . . . . ?
C7 C3 C4 O2 -174.7(11) . . . . ?
C11 C3 C4 O2 8.3(17) . . . . ?
C7 C3 C4 C1 0.0(15) . . . . ?
C11 C3 C4 C1 -177.0(10) . . . . ?
C2 C1 C5 C8 -3.0(17) . . . . ?
C4 C1 C5 C8 178.9(11) . . . . ?
C1 C2 C6 C9 -2.5(16) . . . . ?
O1 C2 C6 C9 178.9(9) . . . . ?
C2 O1 C7 C10 -179.4(10) . . . . ?
C2 O1 C7 C3 -1.6(14) . . . . ?
C11 C3 C7 C10 -4.2(16) . . . . ?
C4 C3 C7 C10 178.6(11) . . . . ?
C11 C3 C7 O1 178.1(9) . . . . ?
C4 C3 C7 O1 0.9(16) . . . . ?
C1 C5 C8 C9 3(2) . . . . ?
C5 C8 C9 C6 -2(2) . . . . ?
C2 C6 C9 C8 1.9(18) . . . . ?
O1 C7 C10 C13 -177.9(10) . . . . ?
C3 C7 C10 C13 4.2(18) . . . . ?
C7 C3 C11 C12 4.1(16) . . . . ?
C4 C3 C11 C12 -178.8(11) . . . . ?
C3 C11 C12 C13 -4(2) . . . . ?
C7 C10 C13 C12 -4(2) . . . . ?
C11 C12 C13 C10 4(2) . . . . ?

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 982623'
#######################################################################
#
#                 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

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 O3'
_chemical_formula_weight         252.26

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   13.5324(8)
_cell_length_b                   7.0687(4)
_cell_length_c                   25.6858(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2457.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    2052
_cell_measurement_theta_min      2.9829
_cell_measurement_theta_max      29.1800

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94773
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_reflns_number            9593
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.347
_diffrn_reflns_theta_max         29.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2871
_reflns_number_gt                2048
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+0.4470P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2871
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.64665(7) 0.24637(15) 0.11449(4) 0.0381(3) Uani 1 1 d . . . . .
O1 O 0.76189(8) 0.08700(19) -0.08604(4) 0.0527(3) Uani 1 1 d . . . . .
O2 O 0.94407(7) 0.2227(2) 0.08778(4) 0.0560(4) Uani 1 1 d . . . . .
C2 C 0.81095(10) 0.1562(2) 0.00292(6) 0.0366(3) Uani 1 1 d . . . . .
H2 H 0.8778 0.1480 -0.0052 0.044 Uiso 1 1 calc R U . . .
C5 C 0.61076(11) 0.1782(2) 0.02672(6) 0.0409(4) Uani 1 1 d . . . . .
H5 H 0.5438 0.1847 0.0348 0.049 Uiso 1 1 calc R U . . .
C7 C 0.85420(10) 0.2304(2) 0.09538(6) 0.0373(4) Uani 1 1 d . . . . .
C6 C 0.64064(11) 0.1398(2) -0.02299(6) 0.0423(4) Uani 1 1 d . . . . .
H6 H 0.5938 0.1213 -0.0490 0.051 Uiso 1 1 calc R U . . .
C1 C 0.74159(11) 0.1282(2) -0.03505(6) 0.0384(4) Uani 1 1 d . . . . .
C10 C 0.66396(11) 0.3135(2) 0.20362(6) 0.0363(3) Uani 1 1 d . . . . .
C4 C 0.68152(10) 0.2073(2) 0.06517(5) 0.0332(3) Uani 1 1 d . . . . .
C9 C 0.71283(11) 0.2766(2) 0.15343(5) 0.0342(3) Uani 1 1 d . . . . .
C11 C 0.71083(12) 0.2659(2) 0.25009(6) 0.0449(4) Uani 1 1 d . . . . .
H11 H 0.7725 0.2080 0.2494 0.054 Uiso 1 1 calc R U . . .
C15 C 0.57122(11) 0.3998(2) 0.20544(6) 0.0433(4) Uani 1 1 d . . . . .
H15 H 0.5388 0.4309 0.1747 0.052 Uiso 1 1 calc R U . . .
C8 C 0.81105(10) 0.2725(2) 0.14531(6) 0.0371(4) Uani 1 1 d . . . . .
H8 H 0.8529 0.2981 0.1732 0.044 Uiso 1 1 calc R U . . .
C12 C 0.66578(14) 0.3045(3) 0.29724(7) 0.0561(5) Uani 1 1 d . . . . .
H12 H 0.6971 0.2718 0.3282 0.067 Uiso 1 1 calc R U . . .
C3 C 0.78142(10) 0.1971(2) 0.05391(6) 0.0330(3) Uani 1 1 d . . . . .
C16 C 0.86215(13) 0.0999(3) -0.10222(7) 0.0653(6) Uani 1 1 d . . . . .
H16A H 0.8666 0.0738 -0.1388 0.098 Uiso 1 1 calc R U . . .
H16B H 0.9011 0.0096 -0.0833 0.098 Uiso 1 1 calc R U . . .
H16C H 0.8865 0.2251 -0.0955 0.098 Uiso 1 1 calc R U . . .
C14 C 0.52740(13) 0.4390(3) 0.25283(7) 0.0533(5) Uani 1 1 d . . . . .
H14 H 0.4659 0.4977 0.2539 0.064 Uiso 1 1 calc R U . . .
C13 C 0.57440(14) 0.3914(3) 0.29849(7) 0.0591(5) Uani 1 1 d . . . . .
H13 H 0.5446 0.4179 0.3303 0.071 Uiso 1 1 calc R U . . .


_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
O3 C9 1.3595(16) . ?
O3 C4 1.3798(16) . ?
O1 C1 1.3697(18) . ?
O1 C16 1.422(2) . ?
O2 C7 1.2329(17) . ?
C2 C1 1.368(2) . ?
C2 C3 1.400(2) . ?
C2 H2 0.9300 . ?
C5 C6 1.367(2) . ?
C5 C4 1.391(2) . ?
C5 H5 0.9300 . ?
C7 C8 1.440(2) . ?
C7 C3 1.470(2) . ?
C6 C1 1.403(2) . ?
C6 H6 0.9300 . ?
C10 C11 1.393(2) . ?
C10 C15 1.396(2) . ?
C10 C9 1.472(2) . ?
C4 C3 1.3843(19) . ?
C9 C8 1.346(2) . ?
C11 C12 1.383(2) . ?
C11 H11 0.9300 . ?
C15 C14 1.382(2) . ?
C15 H15 0.9300 . ?
C8 H8 0.9300 . ?
C12 C13 1.381(3) . ?
C12 H12 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C14 C13 1.376(3) . ?
C14 H14 0.9300 . ?
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
C9 O3 C4 118.80(11) . . ?
C1 O1 C16 117.21(13) . . ?
C1 C2 C3 120.07(13) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C6 C5 C4 119.28(14) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
O2 C7 C8 123.37(13) . . ?
O2 C7 C3 122.64(14) . . ?
C8 C7 C3 113.99(12) . . ?
C5 C6 C1 120.39(14) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C2 C1 O1 125.09(14) . . ?
C2 C1 C6 120.15(14) . . ?
O1 C1 C6 114.76(13) . . ?
C11 C10 C15 119.10(14) . . ?
C11 C10 C9 120.18(13) . . ?
C15 C10 C9 120.71(13) . . ?
O3 C4 C3 122.41(12) . . ?
O3 C4 C5 116.50(12) . . ?
C3 C4 C5 121.09(13) . . ?
C8 C9 O3 122.22(13) . . ?
C8 C9 C10 125.68(13) . . ?
O3 C9 C10 112.10(12) . . ?
C12 C11 C10 120.12(16) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C14 C15 C10 120.18(15) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
C9 C8 C7 122.89(13) . . ?
C9 C8 H8 118.6 . . ?
C7 C8 H8 118.6 . . ?
C13 C12 C11 120.19(16) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C4 C3 C2 119.01(13) . . ?
C4 C3 C7 119.66(13) . . ?
C2 C3 C7 121.33(13) . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C14 C15 120.23(17) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C13 C12 120.18(16) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?

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
C4 C5 C6 C1 0.6(2) . . . . ?
C3 C2 C1 O1 -179.81(15) . . . . ?
C3 C2 C1 C6 -0.2(2) . . . . ?
C16 O1 C1 C2 -9.1(2) . . . . ?
C16 O1 C1 C6 171.27(15) . . . . ?
C5 C6 C1 C2 -0.3(2) . . . . ?
C5 C6 C1 O1 179.32(15) . . . . ?
C9 O3 C4 C3 0.2(2) . . . . ?
C9 O3 C4 C5 -179.81(13) . . . . ?
C6 C5 C4 O3 179.69(14) . . . . ?
C6 C5 C4 C3 -0.3(2) . . . . ?
C4 O3 C9 C8 1.1(2) . . . . ?
C4 O3 C9 C10 -179.17(12) . . . . ?
C11 C10 C9 C8 -28.8(2) . . . . ?
C15 C10 C9 C8 149.96(16) . . . . ?
C11 C10 C9 O3 151.42(14) . . . . ?
C15 C10 C9 O3 -29.81(19) . . . . ?
C15 C10 C11 C12 -0.2(2) . . . . ?
C9 C10 C11 C12 178.59(15) . . . . ?
C11 C10 C15 C14 0.8(2) . . . . ?
C9 C10 C15 C14 -178.03(15) . . . . ?
O3 C9 C8 C7 -2.0(2) . . . . ?
C10 C9 C8 C7 178.28(14) . . . . ?
O2 C7 C8 C9 -178.52(15) . . . . ?
C3 C7 C8 C9 1.5(2) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
O3 C4 C3 C2 179.80(14) . . . . ?
C5 C4 C3 C2 -0.2(2) . . . . ?
O3 C4 C3 C7 -0.5(2) . . . . ?
C5 C4 C3 C7 179.47(14) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C1 C2 C3 C7 -179.20(14) . . . . ?
O2 C7 C3 C4 179.76(15) . . . . ?
C8 C7 C3 C4 -0.3(2) . . . . ?
O2 C7 C3 C2 -0.6(2) . . . . ?
C8 C7 C3 C2 179.38(14) . . . . ?
C10 C15 C14 C13 -0.7(3) . . . . ?
C15 C14 C13 C12 0.1(3) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 982630'
