# 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_m+p21c

# start Validation Reply Form
_vrf_PLAT026_I                   
;
PROBLEM: Ratio Observed / Unique Reflections too Low ....         28 %     
RESPONSE: The available crystals of the title compound diffracted 
very weakly, especially at higher diffraction angles. 
This is most likely related to the fact that the crystals are thin plates.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H12 O'
_chemical_formula_sum            'C17 H12 O'
_chemical_formula_weight         232.27

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   'P2(1)/c  '

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                   13.846(2)
_cell_length_b                   9.3560(19)
_cell_length_c                   10.2300(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.896(11)
_cell_angle_gamma                90.00
_cell_volume                     1296.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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  'STOE IPDS 2T Image Plate diffractometer'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14290
_diffrn_reflns_av_R_equivalents  0.1138
_diffrn_reflns_av_sigmaI/netI    0.0728
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2284
_reflns_number_gt                632
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0000P)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     SHELXL
_refine_ls_extinction_coef       0.0169(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2284
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1991
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1092
_refine_ls_wR_factor_gt          0.0806
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_restrained_S_all      0.624
_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 0.72675(18) 0.0925(3) 0.3204(3) 0.0798(9) Uani 1 1 d . . .
C14 C 0.8049(3) 0.0983(4) 0.4262(4) 0.0601(10) Uani 1 1 d . . .
C11 C 0.9546(3) 0.0852(4) 0.6520(4) 0.0547(9) Uani 1 1 d . . .
C8 C 1.1744(3) 0.0892(4) 0.9770(5) 0.0670(12) Uani 1 1 d . . .
C7 C 1.2423(3) 0.0989(4) 1.0690(4) 0.0657(12) Uani 1 1 d . . .
C9 C 1.0977(3) 0.0821(4) 0.8657(5) 0.0698(12) Uani 1 1 d . . .
C10 C 1.0331(3) 0.0809(4) 0.7695(4) 0.0670(12) Uani 1 1 d . . .
C16 C 0.9563(3) 0.1860(4) 0.5550(4) 0.0668(11) Uani 1 1 d . . .
H16 H 1.0085 0.2505 0.5653 0.080 Uiso 1 1 calc R . .
C15 C 0.8814(3) 0.1932(3) 0.4418(4) 0.0632(11) Uani 1 1 d . . .
H15 H 0.8833 0.2622 0.3770 0.076 Uiso 1 1 calc R . .
C13 C 0.8025(3) -0.0035(4) 0.5233(4) 0.0711(12) Uani 1 1 d . . .
H13 H 0.7501 -0.0676 0.5128 0.085 Uiso 1 1 calc R . .
C5 C 1.3272(3) 0.2290(4) 1.2664(4) 0.0714(12) Uani 1 1 d . . .
H5 H 1.2748 0.2929 1.2565 0.086 Uiso 1 1 calc R . .
C6 C 1.3252(3) 0.1173(4) 1.1783(4) 0.0563(10) Uani 1 1 d . . .
C1 C 1.4042(3) 0.0238(4) 1.1947(4) 0.0752(12) Uani 1 1 d . . .
H1 H 1.4028 -0.0521 1.1357 0.090 Uiso 1 1 calc R . .
C12 C 0.8769(3) -0.0110(4) 0.6356(4) 0.0687(12) Uani 1 1 d . . .
H12 H 0.8751 -0.0803 0.7002 0.082 Uiso 1 1 calc R . .
C4 C 1.4093(4) 0.2450(4) 1.3712(4) 0.0828(13) Uani 1 1 d . . .
H4 H 1.4110 0.3189 1.4324 0.099 Uiso 1 1 calc R . .
C2 C 1.4846(3) 0.0419(5) 1.2973(5) 0.0942(16) Uani 1 1 d . . .
H2 H 1.5375 -0.0212 1.3075 0.113 Uiso 1 1 calc R . .
C3 C 1.4863(4) 0.1526(5) 1.3836(4) 0.0892(14) Uani 1 1 d . . .
H3 H 1.5412 0.1654 1.4523 0.107 Uiso 1 1 calc R . .
C17 C 0.7263(3) 0.1917(4) 0.2153(4) 0.0884(14) Uani 1 1 d . . .
H17A H 0.7288 0.2872 0.2501 0.133 Uiso 1 1 calc R . .
H17B H 0.6670 0.1797 0.1484 0.133 Uiso 1 1 calc R . .
H17C H 0.7826 0.1753 0.1762 0.133 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 0.072(2) 0.0879(18) 0.0697(19) 0.0144(15) -0.0091(15) -0.0126(15)
C14 0.061(3) 0.059(2) 0.062(3) 0.002(2) 0.015(2) 0.003(2)
C11 0.053(3) 0.055(2) 0.056(3) -0.006(2) 0.012(2) -0.001(2)
C8 0.057(3) 0.060(3) 0.083(3) -0.001(2) 0.013(3) 0.005(2)
C7 0.056(3) 0.067(3) 0.072(3) 0.003(2) 0.009(2) 0.002(2)
C9 0.064(3) 0.070(3) 0.071(3) -0.007(2) 0.004(3) 0.005(2)
C10 0.071(3) 0.062(3) 0.065(3) -0.010(2) 0.007(3) 0.008(2)
C16 0.063(3) 0.068(3) 0.068(3) -0.006(2) 0.011(2) -0.020(2)
C15 0.066(3) 0.055(2) 0.068(3) 0.010(2) 0.013(2) -0.013(2)
C13 0.069(3) 0.064(3) 0.075(3) 0.006(2) 0.003(3) -0.022(2)
C5 0.068(3) 0.073(3) 0.073(3) -0.004(2) 0.014(3) -0.004(2)
C6 0.051(3) 0.058(2) 0.058(3) 0.005(2) 0.009(2) 0.001(2)
C1 0.073(3) 0.072(3) 0.077(3) -0.006(2) 0.008(3) 0.009(2)
C12 0.069(3) 0.059(2) 0.076(3) 0.011(2) 0.010(2) -0.003(2)
C4 0.098(4) 0.085(3) 0.065(3) -0.011(2) 0.017(3) -0.016(3)
C2 0.077(4) 0.098(4) 0.094(4) 0.013(3) -0.014(3) 0.015(3)
C3 0.076(4) 0.109(4) 0.072(3) 0.005(3) -0.008(3) -0.020(3)
C17 0.097(4) 0.092(3) 0.069(3) 0.016(3) -0.001(2) 0.009(3)

_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 C14 1.365(4) . ?
O1 C17 1.419(4) . ?
C14 C15 1.366(4) . ?
C14 C13 1.382(4) . ?
C11 C16 1.373(4) . ?
C11 C12 1.386(4) . ?
C11 C10 1.445(5) . ?
C8 C7 1.189(5) . ?
C8 C9 1.388(6) . ?
C7 C6 1.438(5) . ?
C9 C10 1.187(5) . ?
C16 C15 1.387(5) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C13 C12 1.378(5) . ?
C13 H13 0.9300 . ?
C5 C6 1.376(4) . ?
C5 C4 1.400(5) . ?
C5 H5 0.9300 . ?
C6 C1 1.384(4) . ?
C1 C2 1.374(5) . ?
C1 H1 0.9300 . ?
C12 H12 0.9300 . ?
C4 C3 1.359(5) . ?
C4 H4 0.9300 . ?
C2 C3 1.358(5) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C14 O1 C17 117.0(3) . . ?
O1 C14 C15 126.0(4) . . ?
O1 C14 C13 114.2(3) . . ?
C15 C14 C13 119.8(3) . . ?
C16 C11 C12 119.2(3) . . ?
C16 C11 C10 119.9(4) . . ?
C12 C11 C10 120.9(4) . . ?
C7 C8 C9 177.1(6) . . ?
C8 C7 C6 177.3(5) . . ?
C10 C9 C8 177.6(5) . . ?
C9 C10 C11 177.9(5) . . ?
C11 C16 C15 121.0(4) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C14 C15 C16 119.6(4) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C12 C13 C14 120.6(4) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C6 C5 C4 119.1(4) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 119.4(3) . . ?
C5 C6 C7 120.4(4) . . ?
C1 C6 C7 120.2(4) . . ?
C2 C1 C6 120.7(4) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C13 C12 C11 119.8(4) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C3 C4 C5 120.1(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 121.1(4) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C17 O1 C14 C15 1.8(6) . . . . ?
C17 O1 C14 C13 -178.3(3) . . . . ?
C12 C11 C16 C15 0.4(5) . . . . ?
C10 C11 C16 C15 -179.4(4) . . . . ?
O1 C14 C15 C16 -179.8(4) . . . . ?
C13 C14 C15 C16 0.3(6) . . . . ?
C11 C16 C15 C14 -0.3(6) . . . . ?
O1 C14 C13 C12 179.6(4) . . . . ?
C15 C14 C13 C12 -0.5(6) . . . . ?
C4 C5 C6 C1 -0.3(6) . . . . ?
C4 C5 C6 C7 -179.5(4) . . . . ?
C5 C6 C1 C2 -0.4(6) . . . . ?
C7 C6 C1 C2 178.8(4) . . . . ?
C14 C13 C12 C11 0.6(6) . . . . ?
C16 C11 C12 C13 -0.5(6) . . . . ?
C10 C11 C12 C13 179.3(4) . . . . ?
C6 C5 C4 C3 1.2(7) . . . . ?
C6 C1 C2 C3 0.2(7) . . . . ?
C1 C2 C3 C4 0.8(7) . . . . ?
C5 C4 C3 C2 -1.5(7) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.049


_database_code_depnum_ccdc_archive 'CCDC 972614'
