# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 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
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  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.
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data_out

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 O2'
_chemical_formula_sum            'C15 H10 O2'
_chemical_formula_weight         222.23

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           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0356(8)
_cell_length_b                   8.6624(9)
_cell_length_c                   9.2989(10)
_cell_angle_alpha                95.068(3)
_cell_angle_beta                 94.509(3)
_cell_angle_gamma                97.725(3)
_cell_volume                     557.03(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      24.99

_exptl_crystal_description       ?
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             232
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9827
_exptl_absorpt_correction_T_max  0.9827
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6619
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1961
_reflns_number_gt                1720
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.0638P)²+0.0533P] 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         1961
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.1005
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.003

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 0.10218(11) 0.38445(10) 0.17700(9) 0.0550(3) Uani 1 1 d . . .
O2 O 0.39983(13) 0.42614(13) 0.29180(12) 0.0792(3) Uani 1 1 d . . .
C15 C -0.06926(17) 0.44791(14) 0.18781(13) 0.0485(3) Uani 1 1 d . . .
C14 C -0.23053(18) 0.39240(14) 0.10547(13) 0.0521(3) Uani 1 1 d . . .
H14 H -0.3335 0.4464 0.1224 0.062 Uiso 1 1 calc R . .
C13 C 0.24195(17) 0.46366(15) 0.28031(14) 0.0557(3) Uani 1 1 d . . .
C7 C -0.03411(17) 0.57525(13) 0.30473(12) 0.0464(3) Uani 1 1 d . . .
C12 C -0.15306(19) 0.67459(14) 0.36431(14) 0.0568(3) Uani 1 1 d . . .
H12 H -0.2813 0.6688 0.3286 0.068 Uiso 1 1 calc R . .
C6 C -0.27429(18) 0.26127(14) -0.00715(13) 0.0523(3) Uani 1 1 d . . .
C8 C 0.15571(16) 0.58498(13) 0.36034(13) 0.0507(3) Uani 1 1 d . . .
C11 C -0.0737(2) 0.78181(15) 0.47821(15) 0.0646(4) Uani 1 1 d . . .
H11 H -0.1500 0.8503 0.5195 0.078 Uiso 1 1 calc R . .
C1 C -0.1387(2) 0.17105(16) -0.05857(14) 0.0611(4) Uani 1 1 d . . .
H1 H -0.0099 0.1959 -0.0231 0.073 Uiso 1 1 calc R . .
C2 C -0.1953(2) 0.04518(18) -0.16179(16) 0.0738(4) Uani 1 1 d . . .
H2 H -0.1043 -0.0142 -0.1955 0.089 Uiso 1 1 calc R . .
C10 C 0.1168(2) 0.79077(15) 0.53333(16) 0.0685(4) Uani 1 1 d . . .
H10 H 0.1656 0.8649 0.6105 0.082 Uiso 1 1 calc R . .
C5 C -0.4655(2) 0.22105(16) -0.06386(15) 0.0649(4) Uani 1 1 d . . .
H5 H -0.5578 0.2800 -0.0317 0.078 Uiso 1 1 calc R . .
C9 C 0.2347(2) 0.69186(15) 0.47573(15) 0.0627(4) Uani 1 1 d . . .
H9 H 0.3622 0.6967 0.5128 0.075 Uiso 1 1 calc R . .
C3 C -0.3854(3) 0.00713(18) -0.21501(17) 0.0791(5) Uani 1 1 d . . .
H3 H -0.4229 -0.0785 -0.2837 0.095 Uiso 1 1 calc R . .
C4 C -0.5197(3) 0.09524(18) -0.16686(18) 0.0794(5) Uani 1 1 d . . .
H4 H -0.6479 0.0701 -0.2038 0.095 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
O1 0.0496(5) 0.0607(5) 0.0555(5) -0.0035(4) 0.0075(4) 0.0147(4)
O2 0.0486(5) 0.0956(8) 0.0925(8) -0.0098(6) 0.0051(5) 0.0209(5)
C15 0.0499(6) 0.0498(6) 0.0477(6) 0.0061(5) 0.0085(5) 0.0109(5)
C14 0.0545(7) 0.0522(7) 0.0507(7) 0.0038(5) 0.0054(5) 0.0129(5)
C13 0.0470(7) 0.0620(7) 0.0580(7) 0.0034(6) 0.0077(5) 0.0080(5)
C7 0.0524(6) 0.0418(6) 0.0458(6) 0.0061(5) 0.0073(5) 0.0064(5)
C12 0.0598(7) 0.0497(7) 0.0626(8) 0.0040(6) 0.0071(6) 0.0137(6)
C6 0.0629(7) 0.0502(7) 0.0439(6) 0.0068(5) 0.0039(5) 0.0078(6)
C8 0.0522(7) 0.0471(6) 0.0526(7) 0.0069(5) 0.0063(5) 0.0043(5)
C11 0.0837(10) 0.0455(7) 0.0665(8) -0.0018(6) 0.0140(7) 0.0161(6)
C1 0.0663(8) 0.0644(8) 0.0519(7) -0.0020(6) 0.0064(6) 0.0112(6)
C2 0.0919(11) 0.0692(9) 0.0601(9) -0.0080(7) 0.0082(8) 0.0195(8)
C10 0.0896(11) 0.0469(7) 0.0627(8) -0.0069(6) -0.0011(7) 0.0004(7)
C5 0.0655(8) 0.0610(8) 0.0662(9) 0.0022(6) -0.0067(6) 0.0121(6)
C9 0.0619(8) 0.0567(7) 0.0648(8) 0.0025(6) -0.0051(6) -0.0005(6)
C3 0.1044(12) 0.0631(9) 0.0623(9) -0.0107(7) -0.0096(8) 0.0056(8)
C4 0.0815(10) 0.0702(9) 0.0784(10) -0.0028(8) -0.0199(8) 0.0038(8)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C13 1.3835(15) . ?
O1 C15 1.3981(14) . ?
O2 C13 1.1981(15) . ?
C15 C14 1.3253(18) . ?
C15 C7 1.4604(17) . ?
C14 C6 1.4584(17) . ?
C14 H14 0.9300 . ?
C13 C8 1.4597(18) . ?
C7 C8 1.3826(16) . ?
C7 C12 1.3892(17) . ?
C12 C11 1.3748(19) . ?
C12 H12 0.9300 . ?
C6 C5 1.3923(18) . ?
C6 C1 1.3983(18) . ?
C8 C9 1.3820(18) . ?
C11 C10 1.386(2) . ?
C11 H11 0.9300 . ?
C1 C2 1.381(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(2) . ?
C2 H2 0.9300 . ?
C10 C9 1.374(2) . ?
C10 H10 0.9300 . ?
C5 C4 1.377(2) . ?
C5 H5 0.9300 . ?
C9 H9 0.9300 . ?
C3 C4 1.369(2) . ?
C3 H3 0.9300 . ?
C4 H4 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
C13 O1 C15 109.43(9) . . ?
C14 C15 O1 123.07(11) . . ?
C14 C15 C7 129.33(12) . . ?
O1 C15 C7 107.58(10) . . ?
C15 C14 C6 131.12(12) . . ?
C15 C14 H14 114.4 . . ?
C6 C14 H14 114.4 . . ?
O2 C13 O1 120.51(12) . . ?
O2 C13 C8 131.90(13) . . ?
O1 C13 C8 107.59(10) . . ?
C8 C7 C12 120.38(11) . . ?
C8 C7 C15 107.34(10) . . ?
C12 C7 C15 132.26(12) . . ?
C11 C12 C7 117.37(12) . . ?
C11 C12 H12 121.3 . . ?
C7 C12 H12 121.3 . . ?
C5 C6 C1 118.11(12) . . ?
C5 C6 C14 117.38(12) . . ?
C1 C6 C14 124.49(12) . . ?
C9 C8 C7 122.15(12) . . ?
C9 C8 C13 129.74(12) . . ?
C7 C8 C13 108.06(11) . . ?
C12 C11 C10 121.88(13) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C2 C1 C6 120.29(13) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C3 C2 C1 120.40(15) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C9 C10 C11 121.02(13) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C4 C5 C6 120.93(14) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C10 C9 C8 117.19(13) . . ?
C10 C9 H9 121.4 . . ?
C8 C9 H9 121.4 . . ?
C4 C3 C2 120.03(14) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.23(15) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 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
C13 O1 C15 C14 -177.83(11) . . . . ?
C13 O1 C15 C7 0.29(12) . . . . ?
O1 C15 C14 C6 1.1(2) . . . . ?
C7 C15 C14 C6 -176.61(11) . . . . ?
C15 O1 C13 O2 178.66(11) . . . . ?
C15 O1 C13 C8 -0.55(13) . . . . ?
C14 C15 C7 C8 178.06(12) . . . . ?
O1 C15 C7 C8 0.10(12) . . . . ?
C14 C15 C7 C12 -0.1(2) . . . . ?
O1 C15 C7 C12 -178.03(11) . . . . ?
C8 C7 C12 C11 0.55(18) . . . . ?
C15 C7 C12 C11 178.48(11) . . . . ?
C15 C14 C6 C5 173.01(13) . . . . ?
C15 C14 C6 C1 -5.1(2) . . . . ?
C12 C7 C8 C9 0.05(18) . . . . ?
C15 C7 C8 C9 -178.34(11) . . . . ?
C12 C7 C8 C13 177.97(10) . . . . ?
C15 C7 C8 C13 -0.42(13) . . . . ?
O2 C13 C8 C9 -0.8(2) . . . . ?
O1 C13 C8 C9 178.32(12) . . . . ?
O2 C13 C8 C7 -178.47(14) . . . . ?
O1 C13 C8 C7 0.61(13) . . . . ?
C7 C12 C11 C10 -0.57(19) . . . . ?
C5 C6 C1 C2 -0.5(2) . . . . ?
C14 C6 C1 C2 177.52(11) . . . . ?
C6 C1 C2 C3 -0.1(2) . . . . ?
C12 C11 C10 C9 0.0(2) . . . . ?
C1 C6 C5 C4 0.5(2) . . . . ?
C14 C6 C5 C4 -177.70(13) . . . . ?
C11 C10 C9 C8 0.6(2) . . . . ?
C7 C8 C9 C10 -0.64(19) . . . . ?
C13 C8 C9 C10 -178.06(12) . . . . ?
C1 C2 C3 C4 0.7(2) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C6 C5 C4 C3 0.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.078
_database_code_depnum_ccdc_archive 'CCDC 1000643'
