# Electronic Supplementary Material (ESI) for ChemComm.
# 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
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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.
#
data_skkk

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 O3'
_chemical_formula_sum            'C15 H12 O3'
_chemical_formula_weight         240.25

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   P12(1)/c1

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                   9.0155(13)
_cell_length_b                   14.112(2)
_cell_length_c                   9.6804(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.552(5)
_cell_angle_gamma                90.00
_cell_volume                     1231.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.86
_exptl_crystal_size_mid          0.66
_exptl_crystal_size_min          0.44
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9445
_exptl_absorpt_correction_T_max  0.9696
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12609
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         24.51
_reflns_number_total             2027
_reflns_number_gt                1292
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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 > 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)+(0.1134P)²+0.5410P] 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         2027
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.2377
_refine_ls_wR_factor_gt          0.2077
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.050
_refine_ls_shift/su_mean         0.007

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 0.7459(3) 0.10289(18) 0.9941(3) 0.0844(9) Uani 1 1 d . . .
O2 O 0.6010(4) 0.00754(19) 0.8002(4) 0.1091(11) Uani 1 1 d . . .
O3 O 0.9370(3) 0.08358(17) 0.8493(3) 0.0935(10) Uani 1 1 d . . .
C1 C 0.6239(5) -0.3416(3) 0.8611(5) 0.0852(12) Uani 1 1 d . . .
H1 H 0.6146 -0.4071 0.8552 0.102 Uiso 1 1 calc R . .
C2 C 0.5414(5) -0.2842(3) 0.7762(5) 0.0854(12) Uani 1 1 d . . .
H2 H 0.4767 -0.3108 0.7116 0.102 Uiso 1 1 calc R . .
C3 C 0.5534(4) -0.1876(3) 0.7858(4) 0.0803(11) Uani 1 1 d . . .
H3 H 0.4961 -0.1492 0.7284 0.096 Uiso 1 1 calc R . .
C4 C 0.6505(4) -0.1470(2) 0.8805(4) 0.0642(9) Uani 1 1 d . . .
C5 C 0.6589(4) -0.0424(2) 0.8862(4) 0.0693(10) Uani 1 1 d . . .
C6 C 0.7372(4) 0.0007(2) 1.0036(4) 0.0725(10) Uani 1 1 d . . .
H6A H 0.6867 -0.0162 1.0881 0.087 Uiso 1 1 calc R . .
H6B H 0.8369 -0.0250 1.0089 0.087 Uiso 1 1 calc R . .
C7 C 0.8532(4) 0.1361(2) 0.9074(4) 0.0660(9) Uani 1 1 d . . .
C8 C 0.8577(3) 0.2402(2) 0.8989(4) 0.0609(9) Uani 1 1 d . . .
C9 C 0.9514(4) 0.2810(3) 0.8047(4) 0.0766(11) Uani 1 1 d . . .
H9 H 1.0086 0.2427 0.7479 0.092 Uiso 1 1 calc R . .
C10 C 0.9611(4) 0.3784(3) 0.7941(5) 0.0857(12) Uani 1 1 d . . .
H10 H 1.0236 0.4055 0.7292 0.103 Uiso 1 1 calc R . .
C11 C 0.8793(5) 0.4351(3) 0.8783(5) 0.0859(12) Uani 1 1 d . . .
H11 H 0.8859 0.5006 0.8704 0.103 Uiso 1 1 calc R . .
C12 C 0.7209(5) -0.3016(3) 0.9553(5) 0.0913(13) Uani 1 1 d . . .
H12 H 0.7781 -0.3403 1.0124 0.110 Uiso 1 1 calc R . .
C13 C 0.7334(4) -0.2049(2) 0.9653(4) 0.0739(10) Uani 1 1 d . . .
H13 H 0.7983 -0.1785 1.0298 0.089 Uiso 1 1 calc R . .
C14 C 0.7738(4) 0.2970(3) 0.9843(4) 0.0790(11) Uani 1 1 d . . .
H14 H 0.7093 0.2699 1.0475 0.095 Uiso 1 1 calc R . .
C15 C 0.7867(5) 0.3954(3) 0.9751(5) 0.0935(13) Uani 1 1 d . . .
H15 H 0.7330 0.4342 1.0341 0.112 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 0.0843(18) 0.0646(16) 0.105(2) -0.0029(13) 0.0143(16) -0.0008(13)
O2 0.116(2) 0.0670(17) 0.144(3) 0.0200(18) -0.049(2) -0.0008(16)
O3 0.0895(19) 0.0622(16) 0.129(2) -0.0069(16) 0.0300(18) 0.0090(14)
C1 0.087(3) 0.058(2) 0.110(3) -0.008(2) 0.011(3) -0.001(2)
C2 0.080(3) 0.072(3) 0.104(3) -0.011(2) 0.000(2) -0.011(2)
C3 0.071(2) 0.072(2) 0.097(3) -0.002(2) -0.008(2) -0.0004(19)
C4 0.0560(19) 0.057(2) 0.079(2) 0.0028(17) 0.0066(18) -0.0009(16)
C5 0.056(2) 0.060(2) 0.092(3) 0.0097(19) 0.0008(19) 0.0002(16)
C6 0.072(2) 0.057(2) 0.089(3) 0.0165(18) 0.000(2) -0.0053(17)
C7 0.062(2) 0.058(2) 0.079(2) 0.0005(17) 0.0009(19) 0.0029(17)
C8 0.0546(19) 0.0525(19) 0.075(2) -0.0054(15) -0.0047(17) 0.0019(15)
C9 0.073(2) 0.068(2) 0.089(3) 0.002(2) 0.008(2) 0.0041(18)
C10 0.081(3) 0.064(2) 0.112(3) 0.015(2) 0.006(2) -0.006(2)
C11 0.092(3) 0.056(2) 0.110(3) 0.003(2) -0.009(3) -0.004(2)
C12 0.098(3) 0.068(3) 0.107(3) 0.004(2) -0.004(3) 0.010(2)
C13 0.073(2) 0.059(2) 0.089(3) 0.0001(19) -0.007(2) 0.0022(18)
C14 0.087(3) 0.063(2) 0.087(3) -0.0055(19) 0.013(2) 0.0002(19)
C15 0.105(3) 0.065(2) 0.111(3) -0.015(2) 0.013(3) 0.007(2)

_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 1.369(4) . ?
O1 C6 1.447(4) . ?
O2 C5 1.205(4) . ?
O3 C7 1.202(4) . ?
C1 C2 1.369(6) . ?
C1 C12 1.378(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(5) . ?
C3 H3 0.9300 . ?
C4 C13 1.375(5) . ?
C4 C5 1.479(5) . ?
C5 C6 1.464(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.472(5) . ?
C8 C9 1.375(5) . ?
C8 C14 1.382(5) . ?
C9 C10 1.382(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.364(6) . ?
C10 H10 0.9300 . ?
C11 C15 1.379(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.397(5) . ?
C14 H14 0.9300 . ?
C15 H15 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 C6 114.8(3) . . ?
C2 C1 C12 119.5(4) . . ?
C2 C1 H1 120.3 . . ?
C12 C1 H1 120.3 . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.4(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C13 C4 C3 119.0(3) . . ?
C13 C4 C5 122.9(3) . . ?
C3 C4 C5 118.1(3) . . ?
O2 C5 C6 119.7(3) . . ?
O2 C5 C4 122.4(4) . . ?
C6 C5 C4 117.9(3) . . ?
O1 C6 C5 113.0(3) . . ?
O1 C6 H6A 109.0 . . ?
C5 C6 H6A 109.0 . . ?
O1 C6 H6B 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
O3 C7 O1 121.8(3) . . ?
O3 C7 C8 124.8(3) . . ?
O1 C7 C8 113.3(3) . . ?
C9 C8 C14 119.8(3) . . ?
C9 C8 C7 118.2(3) . . ?
C14 C8 C7 122.0(3) . . ?
C8 C9 C10 120.3(4) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 120.3(4) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C15 120.2(4) . . ?
C10 C11 H11 119.9 . . ?
C15 C11 H11 119.9 . . ?
C13 C12 C1 120.4(4) . . ?
C13 C12 H12 119.8 . . ?
C1 C12 H12 119.8 . . ?
C12 C13 C4 120.4(4) . . ?
C12 C13 H13 119.8 . . ?
C4 C13 H13 119.8 . . ?
C8 C14 C15 119.5(4) . . ?
C8 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C11 C15 C14 119.9(4) . . ?
C11 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        24.51
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.049
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.030
;
_database_code_depnum_ccdc_archive 'CCDC 973403'
