# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1510707'
_audit_update_record             
;
2016-10-19 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 O'
_chemical_formula_weight         282.32

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)/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                   9.567(5)
_cell_length_b                   17.241(9)
_cell_length_c                   9.945(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.813(8)
_cell_angle_gamma                90.00
_cell_volume                     1533.3(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2768
_cell_measurement_theta_min      2.489
_cell_measurement_theta_max      23.956

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.2000
_exptl_absorpt_correction_T_max  1.0000
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9431
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         28.24
_reflns_number_total             3690
_reflns_number_gt                2415
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0444P)²+0.1303P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    contr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3690
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.18959(12) 0.08088(7) 0.07593(10) 0.0683(3) Uani 1 1 d . . .
C8 C 0.34163(14) 0.13322(7) -0.18372(13) 0.0442(3) Uani 1 1 d . . .
C9 C 0.21736(15) 0.11869(7) -0.15027(13) 0.0444(3) Uani 1 1 d . . .
C10 C 0.05773(15) 0.12395(7) -0.24102(13) 0.0456(3) Uani 1 1 d . . .
C7 C 0.47960(15) 0.11879(7) -0.05540(13) 0.0472(3) Uani 1 1 d . . .
C1 C 0.26932(16) 0.09508(8) 0.00602(13) 0.0495(3) Uani 1 1 d . . .
C2 C 0.43573(16) 0.09509(8) 0.05917(13) 0.0507(3) Uani 1 1 d . . .
C15 C -0.04402(16) 0.06902(8) -0.22671(15) 0.0559(4) Uani 1 1 d . . .
H15A H -0.0106 0.0301 -0.1579 0.067 Uiso 1 1 calc R . .
C16 C 0.34825(14) 0.15741(8) -0.32471(13) 0.0480(3) Uani 1 1 d . . .
C11 C 0.00263(16) 0.18277(8) -0.34391(14) 0.0546(3) Uani 1 1 d . . .
H11A H 0.0673 0.2207 -0.3540 0.066 Uiso 1 1 calc R . .
C6 C 0.62938(16) 0.12133(8) -0.03797(16) 0.0586(4) Uani 1 1 d . . .
H6A H 0.6596 0.1367 -0.1130 0.070 Uiso 1 1 calc R . .
C21 C 0.43532(16) 0.22070(9) -0.33316(17) 0.0599(4) Uani 1 1 d . . .
H21A H 0.4923 0.2467 -0.2498 0.072 Uiso 1 1 calc R . .
C17 C 0.26679(17) 0.11802(9) -0.45032(14) 0.0603(4) Uani 1 1 d . . .
H17A H 0.2096 0.0751 -0.4460 0.072 Uiso 1 1 calc R . .
C14 C -0.19310(17) 0.07181(10) -0.31324(17) 0.0659(4) Uani 1 1 d . . .
H14A H -0.2591 0.0349 -0.3023 0.079 Uiso 1 1 calc R . .
C13 C -0.24492(18) 0.12906(10) -0.41589(17) 0.0688(4) Uani 1 1 d . . .
H13A H -0.3451 0.1303 -0.4751 0.083 Uiso 1 1 calc R . .
C3 C 0.53988(18) 0.07476(9) 0.19096(15) 0.0640(4) Uani 1 1 d . . .
H3A H 0.5101 0.0594 0.2664 0.077 Uiso 1 1 calc R . .
C12 C -0.14621(18) 0.18482(10) -0.43004(16) 0.0661(4) Uani 1 1 d . . .
H12A H -0.1810 0.2239 -0.4983 0.079 Uiso 1 1 calc R . .
C4 C 0.69083(19) 0.07784(9) 0.20797(17) 0.0710(5) Uani 1 1 d . . .
H4A H 0.7629 0.0647 0.2961 0.085 Uiso 1 1 calc R . .
C19 C 0.3547(2) 0.20592(13) -0.5893(2) 0.0837(6) Uani 1 1 d . . .
H19A H 0.3559 0.2224 -0.6779 0.100 Uiso 1 1 calc R . .
C20 C 0.43721(19) 0.24508(11) -0.4660(2) 0.0769(5) Uani 1 1 d . . .
H20A H 0.4942 0.2878 -0.4715 0.092 Uiso 1 1 calc R . .
C18 C 0.2704(2) 0.14247(11) -0.58198(16) 0.0763(5) Uani 1 1 d . . .
H18A H 0.2158 0.1159 -0.6655 0.092 Uiso 1 1 calc R . .
C5 C 0.73458(18) 0.10015(9) 0.09592(18) 0.0686(4) Uani 1 1 d . . .
H5A H 0.8358 0.1012 0.1093 0.082 Uiso 1 1 calc R . .


_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 C1 1.2256(16) . ?
C8 C9 1.3667(18) . ?
C8 C16 1.4856(18) . ?
C8 C7 1.4952(18) . ?
C9 C10 1.475(2) . ?
C9 C1 1.5099(19) . ?
C10 C15 1.4012(19) . ?
C10 C11 1.4036(19) . ?
C7 C6 1.382(2) . ?
C7 C2 1.4075(19) . ?
C1 C2 1.489(2) . ?
C2 C3 1.3804(19) . ?
C15 C14 1.380(2) . ?
C16 C17 1.392(2) . ?
C16 C21 1.393(2) . ?
C11 C12 1.377(2) . ?
C6 C5 1.402(2) . ?
C21 C20 1.393(2) . ?
C17 C18 1.388(2) . ?
C14 C13 1.379(2) . ?
C13 C12 1.389(2) . ?
C3 C4 1.394(2) . ?
C4 C5 1.377(2) . ?
C19 C20 1.376(3) . ?
C19 C18 1.376(3) . ?

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 C8 C16 127.86(12) . . ?
C9 C8 C7 110.01(11) . . ?
C16 C8 C7 122.11(12) . . ?
C8 C9 C10 129.85(11) . . ?
C8 C9 C1 107.66(12) . . ?
C10 C9 C1 122.49(11) . . ?
C15 C10 C11 117.90(13) . . ?
C15 C10 C9 120.12(12) . . ?
C11 C10 C9 121.98(12) . . ?
C6 C7 C2 120.13(13) . . ?
C6 C7 C8 131.57(12) . . ?
C2 C7 C8 108.21(12) . . ?
O1 C1 C2 126.96(12) . . ?
O1 C1 C9 126.46(13) . . ?
C2 C1 C9 106.55(11) . . ?
C3 C2 C7 121.34(14) . . ?
C3 C2 C1 131.08(13) . . ?
C7 C2 C1 107.55(11) . . ?
C14 C15 C10 120.95(14) . . ?
C17 C16 C21 118.95(13) . . ?
C17 C16 C8 120.80(12) . . ?
C21 C16 C8 120.24(12) . . ?
C12 C11 C10 120.64(14) . . ?
C7 C6 C5 118.25(14) . . ?
C20 C21 C16 120.20(16) . . ?
C18 C17 C16 120.32(16) . . ?
C13 C14 C15 120.43(15) . . ?
C14 C13 C12 119.45(15) . . ?
C2 C3 C4 118.21(15) . . ?
C11 C12 C13 120.60(14) . . ?
C5 C4 C3 120.80(14) . . ?
C20 C19 C18 120.30(15) . . ?
C19 C20 C21 120.02(17) . . ?
C19 C18 C17 120.18(17) . . ?
C4 C5 C6 121.27(16) . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        28.24
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.027
