# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1407467'
_audit_update_record             
;
2015-06-17 deposited with the CCDC.
2015-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H16 O2'
_chemical_formula_sum            'C23 H16 O2'
_chemical_formula_weight         324.36

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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.0152(7)
_cell_length_b                   15.450(2)
_cell_length_c                   20.528(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1590.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    204
_cell_measurement_theta_min      3
_cell_measurement_theta_max      67

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   0.808
_exptl_transmission_factor_max   0.868
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.676
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11948
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.580
_diffrn_reflns_theta_max         64.996
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.909
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.909
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.901
_reflns_number_total             2580
_reflns_number_gt                2508
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.670
_reflns_Friedel_fraction_max     0.949
_reflns_Friedel_fraction_full    0.890

_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       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.2000P)²] 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_abs_structure_details 
;
 Flack x determined using 970 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2580
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0672
_refine_ls_wR_factor_ref         0.2060
_refine_ls_wR_factor_gt          0.2033
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 0.2473(5) 0.99105(17) 0.66128(11) 0.0305(7) Uani 1 1 d . . . . .
O2 O -0.1352(6) 1.00433(17) 0.75933(12) 0.0349(8) Uani 1 1 d . . . . .
C1 C 0.0500(6) 0.9960(2) 0.54855(16) 0.0202(8) Uani 1 1 d . . . . .
C2 C 0.2389(6) 0.9439(2) 0.51643(17) 0.0207(8) Uani 1 1 d . . . . .
C3 C 0.3938(7) 0.8792(2) 0.54857(15) 0.0216(7) Uani 1 1 d . . . . .
H3A H 0.3664 0.8687 0.5937 0.026 Uiso 1 1 calc R U . . .
C4 C 0.5800(7) 0.8323(2) 0.51579(18) 0.0250(8) Uani 1 1 d . . . . .
H4A H 0.6802 0.7895 0.5382 0.030 Uiso 1 1 calc R U . . .
C5 C 0.6265(7) 0.8466(2) 0.44816(17) 0.0243(8) Uani 1 1 d . . . . .
H5A H 0.7589 0.8140 0.4259 0.029 Uiso 1 1 calc R U . . .
C6 C 0.4812(7) 0.9070(2) 0.41544(17) 0.0235(8) Uani 1 1 d . . . . .
H6A H 0.5145 0.9164 0.3704 0.028 Uiso 1 1 calc R U . . .
C7 C 0.2797(7) 0.9567(2) 0.44741(17) 0.0208(8) Uani 1 1 d . . . . .
C8 C 0.1268(6) 1.0170(2) 0.41392(16) 0.0218(8) Uani 1 1 d . . . . .
H8A H 0.1580 1.0256 0.3687 0.026 Uiso 1 1 calc R U . . .
C9 C -0.0710(6) 1.0651(2) 0.44486(16) 0.0204(8) Uani 1 1 d . . . . .
C10 C -0.2367(7) 1.1240(2) 0.40982(16) 0.0232(8) Uani 1 1 d . . . . .
H10A H -0.2108 1.1313 0.3643 0.028 Uiso 1 1 calc R U . . .
C11 C -0.4314(7) 1.1701(2) 0.44051(19) 0.0257(8) Uani 1 1 d . . . . .
H11A H -0.5418 1.2082 0.4162 0.031 Uiso 1 1 calc R U . . .
C12 C -0.4699(7) 1.1613(2) 0.50871(18) 0.0250(8) Uani 1 1 d . . . . .
H12A H -0.6039 1.1943 0.5300 0.030 Uiso 1 1 calc R U . . .
C13 C -0.3151(7) 1.1055(2) 0.54389(16) 0.0234(8) Uani 1 1 d . . . . .
H13A H -0.3441 1.1003 0.5895 0.028 Uiso 1 1 calc R U . . .
C14 C -0.1113(6) 1.0549(2) 0.51402(16) 0.0203(8) Uani 1 1 d . . . . .
C15 C 0.0133(7) 0.9875(2) 0.62060(16) 0.0222(8) Uani 1 1 d . . . . .
H15A H -0.1287 0.9463 0.6349 0.027 Uiso 1 1 calc R U . . .
C16 C 0.0633(7) 1.0610(2) 0.66452(16) 0.0235(8) Uani 1 1 d . . . . .
H16A H 0.1198 1.1166 0.6437 0.028 Uiso 1 1 calc R U . . .
C17 C -0.1012(7) 1.0683(2) 0.72544(16) 0.0238(8) Uani 1 1 d . . . . .
C18 C -0.2293(7) 1.1520(2) 0.74143(15) 0.0237(8) Uani 1 1 d . . . . .
C19 C -0.4491(7) 1.1528(3) 0.78327(16) 0.0263(8) Uani 1 1 d . . . . .
H19A H -0.5167 1.0997 0.7998 0.032 Uiso 1 1 calc R U . . .
C20 C -0.5692(7) 1.2297(3) 0.80093(17) 0.0312(9) Uani 1 1 d . . . . .
H20A H -0.7166 1.2295 0.8300 0.037 Uiso 1 1 calc R U . . .
C21 C -0.4740(8) 1.3072(2) 0.77608(18) 0.0300(9) Uani 1 1 d . . . . .
H21A H -0.5609 1.3599 0.7869 0.036 Uiso 1 1 calc R U . . .
C22 C -0.2535(8) 1.3083(2) 0.73568(17) 0.0308(9) Uani 1 1 d . . . . .
H22A H -0.1841 1.3618 0.7205 0.037 Uiso 1 1 calc R U . . .
C23 C -0.1331(7) 1.2307(2) 0.71731(16) 0.0269(8) Uani 1 1 d . . . . .
H23A H 0.0147 1.2313 0.6883 0.032 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 C16 1.423(4) . ?
O1 C15 1.441(4) . ?
O2 C17 1.220(4) . ?
C1 C2 1.407(5) . ?
C1 C14 1.409(5) . ?
C1 C15 1.496(5) . ?
C2 C3 1.428(5) . ?
C2 C7 1.445(5) . ?
C3 C4 1.360(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.425(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.361(5) . ?
C5 H5A 0.9500 . ?
C6 C7 1.428(5) . ?
C6 H6A 0.9500 . ?
C7 C8 1.389(5) . ?
C8 C9 1.393(5) . ?
C8 H8A 0.9500 . ?
C9 C10 1.428(5) . ?
C9 C14 1.443(5) . ?
C10 C11 1.362(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.420(5) . ?
C11 H11A 0.9500 . ?
C12 C13 1.366(5) . ?
C12 H12A 0.9500 . ?
C13 C14 1.426(5) . ?
C13 H13A 0.9500 . ?
C15 C16 1.471(5) . ?
C15 H15A 1.0000 . ?
C16 C17 1.502(5) . ?
C16 H16A 1.0000 . ?
C17 C18 1.481(5) . ?
C18 C19 1.398(5) . ?
C18 C23 1.398(5) . ?
C19 C20 1.380(5) . ?
C19 H19A 0.9500 . ?
C20 C21 1.387(6) . ?
C20 H20A 0.9500 . ?
C21 C22 1.382(6) . ?
C21 H21A 0.9500 . ?
C22 C23 1.394(5) . ?
C22 H22A 0.9500 . ?
C23 H23A 0.9500 . ?

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
C16 O1 C15 61.8(2) . . ?
C2 C1 C14 121.3(3) . . ?
C2 C1 C15 119.8(3) . . ?
C14 C1 C15 118.9(3) . . ?
C1 C2 C3 123.4(3) . . ?
C1 C2 C7 118.5(3) . . ?
C3 C2 C7 118.1(3) . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3A 119.4 . . ?
C2 C3 H3A 119.4 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C5 C6 C7 121.3(3) . . ?
C5 C6 H6A 119.3 . . ?
C7 C6 H6A 119.3 . . ?
C8 C7 C6 121.6(3) . . ?
C8 C7 C2 119.9(3) . . ?
C6 C7 C2 118.5(3) . . ?
C7 C8 C9 121.7(3) . . ?
C7 C8 H8A 119.1 . . ?
C9 C8 H8A 119.1 . . ?
C8 C9 C10 121.7(3) . . ?
C8 C9 C14 119.3(3) . . ?
C10 C9 C14 118.9(3) . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10A 119.4 . . ?
C9 C10 H10A 119.4 . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11A 119.9 . . ?
C12 C11 H11A 119.9 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C12 C13 C14 121.7(3) . . ?
C12 C13 H13A 119.1 . . ?
C14 C13 H13A 119.1 . . ?
C1 C14 C13 123.3(3) . . ?
C1 C14 C9 119.0(3) . . ?
C13 C14 C9 117.6(3) . . ?
O1 C15 C16 58.5(2) . . ?
O1 C15 C1 118.0(3) . . ?
C16 C15 C1 121.2(3) . . ?
O1 C15 H15A 115.7 . . ?
C16 C15 H15A 115.7 . . ?
C1 C15 H15A 115.7 . . ?
O1 C16 C15 59.7(2) . . ?
O1 C16 C17 116.8(3) . . ?
C15 C16 C17 118.3(3) . . ?
O1 C16 H16A 116.6 . . ?
C15 C16 H16A 116.6 . . ?
C17 C16 H16A 116.6 . . ?
O2 C17 C18 121.3(3) . . ?
O2 C17 C16 119.4(3) . . ?
C18 C17 C16 119.2(3) . . ?
C19 C18 C23 118.9(3) . . ?
C19 C18 C17 119.0(3) . . ?
C23 C18 C17 122.1(3) . . ?
C20 C19 C18 120.8(3) . . ?
C20 C19 H19A 119.6 . . ?
C18 C19 H19A 119.6 . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 H20A 120.1 . . ?
C21 C20 H20A 120.1 . . ?
C22 C21 C20 120.4(3) . . ?
C22 C21 H21A 119.8 . . ?
C20 C21 H21A 119.8 . . ?
C21 C22 C23 119.9(3) . . ?
C21 C22 H22A 120.1 . . ?
C23 C22 H22A 120.1 . . ?
C22 C23 C18 120.1(3) . . ?
C22 C23 H23A 119.9 . . ?
C18 C23 H23A 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
C14 C1 C2 C3 -175.6(3) . . . . ?
C15 C1 C2 C3 2.8(5) . . . . ?
C14 C1 C2 C7 4.8(4) . . . . ?
C15 C1 C2 C7 -176.8(3) . . . . ?
C1 C2 C3 C4 -177.9(3) . . . . ?
C7 C2 C3 C4 1.7(5) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C4 C5 C6 C7 -0.4(6) . . . . ?
C5 C6 C7 C8 -178.5(3) . . . . ?
C5 C6 C7 C2 2.3(5) . . . . ?
C1 C2 C7 C8 -2.4(5) . . . . ?
C3 C2 C7 C8 177.9(3) . . . . ?
C1 C2 C7 C6 176.8(3) . . . . ?
C3 C2 C7 C6 -2.9(4) . . . . ?
C6 C7 C8 C9 179.6(3) . . . . ?
C2 C7 C8 C9 -1.3(5) . . . . ?
C7 C8 C9 C10 -177.0(3) . . . . ?
C7 C8 C9 C14 2.7(5) . . . . ?
C8 C9 C10 C11 179.3(3) . . . . ?
C14 C9 C10 C11 -0.3(5) . . . . ?
C9 C10 C11 C12 1.2(5) . . . . ?
C10 C11 C12 C13 -1.1(5) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
C2 C1 C14 C13 176.5(3) . . . . ?
C15 C1 C14 C13 -2.0(5) . . . . ?
C2 C1 C14 C9 -3.4(5) . . . . ?
C15 C1 C14 C9 178.2(3) . . . . ?
C12 C13 C14 C1 -179.2(3) . . . . ?
C12 C13 C14 C9 0.6(5) . . . . ?
C8 C9 C14 C1 -0.4(5) . . . . ?
C10 C9 C14 C1 179.3(3) . . . . ?
C8 C9 C14 C13 179.8(3) . . . . ?
C10 C9 C14 C13 -0.6(5) . . . . ?
C16 O1 C15 C1 111.2(3) . . . . ?
C2 C1 C15 O1 50.5(4) . . . . ?
C14 C1 C15 O1 -131.1(3) . . . . ?
C2 C1 C15 C16 118.7(4) . . . . ?
C14 C1 C15 C16 -62.8(4) . . . . ?
C15 O1 C16 C17 108.7(3) . . . . ?
C1 C15 C16 O1 -105.8(3) . . . . ?
O1 C15 C16 C17 -106.2(3) . . . . ?
C1 C15 C16 C17 148.0(3) . . . . ?
O1 C16 C17 O2 -22.2(5) . . . . ?
C15 C16 C17 O2 46.1(5) . . . . ?
O1 C16 C17 C18 160.7(3) . . . . ?
C15 C16 C17 C18 -131.0(3) . . . . ?
O2 C17 C18 C19 -18.9(5) . . . . ?
C16 C17 C18 C19 158.2(3) . . . . ?
O2 C17 C18 C23 159.4(3) . . . . ?
C16 C17 C18 C23 -23.5(5) . . . . ?
C23 C18 C19 C20 -0.3(5) . . . . ?
C17 C18 C19 C20 178.0(3) . . . . ?
C18 C19 C20 C21 1.1(5) . . . . ?
C19 C20 C21 C22 -2.4(6) . . . . ?
C20 C21 C22 C23 3.0(6) . . . . ?
C21 C22 C23 C18 -2.2(5) . . . . ?
C19 C18 C23 C22 0.9(5) . . . . ?
C17 C18 C23 C22 -177.5(3) . . . . ?

_refine_diff_density_max         0.488
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.112

_shelxl_version_number           2014/6

