# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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_X
_database_code_depnum_ccdc_archive 'CCDC 1063123'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 O2'
_chemical_formula_weight         338.38

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'

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

_cell_length_a                   10.669(2)
_cell_length_b                   11.771(2)
_cell_length_c                   14.278(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1793.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3286
_cell_measurement_theta_min      2.242
_cell_measurement_theta_max      25.363

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3286
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.242
_diffrn_reflns_theta_max         25.363
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1887
_reflns_number_gt                1068
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1998)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_number_reflns         1887
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1189
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1862
_refine_ls_wR_factor_gt          0.1496
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.067
_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 0.3369(4) 0.2794(3) -0.0316(3) 0.0667(12) Uani 1 1 d . . . . .
O2 O 0.6573(4) 0.5910(4) -0.2981(3) 0.0823(14) Uani 1 1 d . . . . .
C1 C 0.5888(6) -0.0865(5) 0.0469(4) 0.0652(16) Uani 1 1 d . . . . .
C2 C 0.5553(7) -0.1071(7) -0.0491(5) 0.086(2) Uani 1 1 d . . . . .
H2A H 0.5064 -0.0547 -0.0813 0.103 Uiso 1 1 calc R U . . .
C3 C 0.5948(9) -0.2028(8) -0.0929(6) 0.108(3) Uani 1 1 d . . . . .
H3A H 0.5726 -0.2149 -0.1551 0.129 Uiso 1 1 calc R U . . .
C4 C 0.6690(10) -0.2843(7) -0.0462(7) 0.118(3) Uani 1 1 d . . . . .
H4A H 0.6953 -0.3493 -0.0776 0.141 Uiso 1 1 calc R U . . .
C5 C 0.7016(8) -0.2678(6) 0.0443(6) 0.093(2) Uani 1 1 d . . . . .
H5A H 0.7513 -0.3215 0.0744 0.112 Uiso 1 1 calc R U . . .
C6 C 0.6617(6) -0.1703(5) 0.0943(5) 0.0683(17) Uani 1 1 d . . . . .
C7 C 0.6857(6) -0.1570(5) 0.1889(5) 0.0704(18) Uani 1 1 d . . . . .
H7A H 0.7311 -0.2129 0.2199 0.084 Uiso 1 1 calc R U . . .
C8 C 0.6451(5) -0.0646(5) 0.2387(4) 0.0592(15) Uani 1 1 d . . . . .
C9 C 0.6666(6) -0.0536(6) 0.3364(5) 0.0740(18) Uani 1 1 d . . . . .
H9A H 0.7074 -0.1121 0.3678 0.089 Uiso 1 1 calc R U . . .
C10 C 0.6304(7) 0.0374(7) 0.3845(5) 0.089(2) Uani 1 1 d . . . . .
H10A H 0.6435 0.0416 0.4488 0.107 Uiso 1 1 calc R U . . .
C11 C 0.5708(6) 0.1288(6) 0.3356(5) 0.0832(19) Uani 1 1 d . . . . .
H11A H 0.5490 0.1945 0.3680 0.100 Uiso 1 1 calc R U . . .
C12 C 0.5459(5) 0.1210(5) 0.2433(5) 0.0730(18) Uani 1 1 d . . . . .
H12A H 0.5053 0.1810 0.2138 0.088 Uiso 1 1 calc R U . . .
C13 C 0.5795(5) 0.0241(5) 0.1898(4) 0.0571(14) Uani 1 1 d . . . . .
C14 C 0.5516(5) 0.0122(5) 0.0944(4) 0.0592(15) Uani 1 1 d . . . . .
C15 C 0.4829(6) 0.1036(6) 0.0455(4) 0.079(2) Uani 1 1 d . . . . .
H15A H 0.3959 0.0990 0.0481 0.095 Uiso 1 1 calc R U . . .
C16 C 0.5267(5) 0.1871(5) 0.0008(4) 0.0642(16) Uani 1 1 d . . . . .
H16A H 0.6134 0.1936 -0.0035 0.077 Uiso 1 1 calc R U . . .
C17 C 0.4496(5) 0.2755(4) -0.0454(3) 0.0500(13) Uani 1 1 d . . . . .
C18 C 0.5101(5) 0.3575(4) -0.1097(4) 0.0492(13) Uani 1 1 d . . . . .
C19 C 0.4347(5) 0.4356(5) -0.1578(4) 0.0668(16) Uani 1 1 d . . . . .
H19A H 0.3485 0.4356 -0.1482 0.080 Uiso 1 1 calc R U . . .
C20 C 0.4873(6) 0.5122(5) -0.2189(4) 0.0736(19) Uani 1 1 d . . . . .
H20A H 0.4367 0.5647 -0.2495 0.088 Uiso 1 1 calc R U . . .
C21 C 0.6153(5) 0.5115(5) -0.2351(4) 0.0567(15) Uani 1 1 d . . . . .
C22 C 0.6909(5) 0.4364(4) -0.1888(4) 0.0584(15) Uani 1 1 d . . . . .
H22A H 0.7770 0.4369 -0.1988 0.070 Uiso 1 1 calc R U . . .
C23 C 0.6379(5) 0.3595(4) -0.1267(4) 0.0553(15) Uani 1 1 d . . . . .
H23A H 0.6894 0.3079 -0.0958 0.066 Uiso 1 1 calc R U . . .
C24 C 0.7872(6) 0.5974(6) -0.3155(6) 0.094(2) Uani 1 1 d . . . . .
H24A H 0.8031 0.6547 -0.3619 0.142 Uiso 1 1 calc R U . . .
H24B H 0.8166 0.5253 -0.3380 0.142 Uiso 1 1 calc R U . . .
H24C H 0.8302 0.6166 -0.2586 0.142 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 C17 1.219(6) . ?
O2 C21 1.372(6) . ?
O2 C24 1.410(7) . ?
C1 C14 1.403(8) . ?
C1 C6 1.427(8) . ?
C1 C2 1.438(8) . ?
C2 C3 1.355(9) . ?
C2 H2A 0.9300 . ?
C3 C4 1.411(12) . ?
C3 H3A 0.9300 . ?
C4 C5 1.353(10) . ?
C4 H4A 0.9300 . ?
C5 C6 1.417(9) . ?
C5 H5A 0.9300 . ?
C6 C7 1.383(9) . ?
C7 C8 1.370(8) . ?
C7 H7A 0.9300 . ?
C8 C9 1.419(8) . ?
C8 C13 1.438(8) . ?
C9 C10 1.331(9) . ?
C9 H9A 0.9300 . ?
C10 C11 1.432(9) . ?
C10 H10A 0.9300 . ?
C11 C12 1.348(9) . ?
C11 H11A 0.9300 . ?
C12 C13 1.419(8) . ?
C12 H12A 0.9300 . ?
C13 C14 1.401(8) . ?
C14 C15 1.477(8) . ?
C15 C16 1.262(7) . ?
C15 H15A 0.9300 . ?
C16 C17 1.481(7) . ?
C16 H16A 0.9300 . ?
C17 C18 1.480(7) . ?
C18 C23 1.385(7) . ?
C18 C19 1.401(7) . ?
C19 C20 1.375(8) . ?
C19 H19A 0.9300 . ?
C20 C21 1.385(8) . ?
C20 H20A 0.9300 . ?
C21 C22 1.367(7) . ?
C22 C23 1.387(7) . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C21 O2 C24 118.2(5) . . ?
C14 C1 C6 119.9(6) . . ?
C14 C1 C2 122.0(6) . . ?
C6 C1 C2 118.1(6) . . ?
C3 C2 C1 120.2(7) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C2 C3 C4 121.4(8) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C5 C4 C3 119.9(8) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
C4 C5 C6 121.4(8) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C7 C6 C5 121.9(6) . . ?
C7 C6 C1 119.0(6) . . ?
C5 C6 C1 119.0(6) . . ?
C8 C7 C6 122.6(6) . . ?
C8 C7 H7A 118.7 . . ?
C6 C7 H7A 118.7 . . ?
C7 C8 C9 122.1(6) . . ?
C7 C8 C13 118.5(5) . . ?
C9 C8 C13 119.3(6) . . ?
C10 C9 C8 122.3(7) . . ?
C10 C9 H9A 118.8 . . ?
C8 C9 H9A 118.8 . . ?
C9 C10 C11 118.8(6) . . ?
C9 C10 H10A 120.6 . . ?
C11 C10 H10A 120.6 . . ?
C12 C11 C10 120.9(7) . . ?
C12 C11 H11A 119.6 . . ?
C10 C11 H11A 119.6 . . ?
C11 C12 C13 122.2(6) . . ?
C11 C12 H12A 118.9 . . ?
C13 C12 H12A 118.9 . . ?
C14 C13 C12 123.4(5) . . ?
C14 C13 C8 120.2(5) . . ?
C12 C13 C8 116.4(5) . . ?
C13 C14 C1 119.5(5) . . ?
C13 C14 C15 119.5(5) . . ?
C1 C14 C15 121.1(5) . . ?
C16 C15 C14 128.5(6) . . ?
C16 C15 H15A 115.7 . . ?
C14 C15 H15A 115.7 . . ?
C15 C16 C17 124.5(5) . . ?
C15 C16 H16A 117.7 . . ?
C17 C16 H16A 117.7 . . ?
O1 C17 C18 120.3(5) . . ?
O1 C17 C16 120.2(5) . . ?
C18 C17 C16 119.5(5) . . ?
C23 C18 C19 117.9(5) . . ?
C23 C18 C17 123.3(5) . . ?
C19 C18 C17 118.8(5) . . ?
C20 C19 C18 120.4(5) . . ?
C20 C19 H19A 119.8 . . ?
C18 C19 H19A 119.8 . . ?
C19 C20 C21 120.3(5) . . ?
C19 C20 H20A 119.8 . . ?
C21 C20 H20A 119.8 . . ?
C22 C21 O2 124.4(5) . . ?
C22 C21 C20 120.3(5) . . ?
O2 C21 C20 115.3(5) . . ?
C21 C22 C23 119.4(5) . . ?
C21 C22 H22A 120.3 . . ?
C23 C22 H22A 120.3 . . ?
C18 C23 C22 121.6(5) . . ?
C18 C23 H23A 119.2 . . ?
C22 C23 H23A 119.2 . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C14 C1 C2 C3 179.0(6) . . . . ?
C6 C1 C2 C3 -1.3(10) . . . . ?
C1 C2 C3 C4 0.1(12) . . . . ?
C2 C3 C4 C5 0.2(14) . . . . ?
C3 C4 C5 C6 0.7(13) . . . . ?
C4 C5 C6 C7 174.5(7) . . . . ?
C4 C5 C6 C1 -1.9(11) . . . . ?
C14 C1 C6 C7 5.3(8) . . . . ?
C2 C1 C6 C7 -174.4(6) . . . . ?
C14 C1 C6 C5 -178.1(5) . . . . ?
C2 C1 C6 C5 2.2(9) . . . . ?
C5 C6 C7 C8 -178.3(6) . . . . ?
C1 C6 C7 C8 -1.9(9) . . . . ?
C6 C7 C8 C9 177.8(6) . . . . ?
C6 C7 C8 C13 -2.6(9) . . . . ?
C7 C8 C9 C10 178.1(6) . . . . ?
C13 C8 C9 C10 -1.4(9) . . . . ?
C8 C9 C10 C11 -1.8(10) . . . . ?
C9 C10 C11 C12 3.3(10) . . . . ?
C10 C11 C12 C13 -1.5(10) . . . . ?
C11 C12 C13 C14 178.1(6) . . . . ?
C11 C12 C13 C8 -1.7(9) . . . . ?
C7 C8 C13 C14 3.8(8) . . . . ?
C9 C8 C13 C14 -176.7(5) . . . . ?
C7 C8 C13 C12 -176.4(5) . . . . ?
C9 C8 C13 C12 3.1(8) . . . . ?
C12 C13 C14 C1 179.8(5) . . . . ?
C8 C13 C14 C1 -0.4(8) . . . . ?
C12 C13 C14 C15 -0.5(8) . . . . ?
C8 C13 C14 C15 179.3(5) . . . . ?
C6 C1 C14 C13 -4.2(8) . . . . ?
C2 C1 C14 C13 175.5(6) . . . . ?
C6 C1 C14 C15 176.2(5) . . . . ?
C2 C1 C14 C15 -4.1(9) . . . . ?
C13 C14 C15 C16 92.5(8) . . . . ?
C1 C14 C15 C16 -87.8(8) . . . . ?
C14 C15 C16 C17 -179.4(6) . . . . ?
C15 C16 C17 O1 9.7(9) . . . . ?
C15 C16 C17 C18 -169.2(6) . . . . ?
O1 C17 C18 C23 178.4(5) . . . . ?
C16 C17 C18 C23 -2.7(8) . . . . ?
O1 C17 C18 C19 -3.2(7) . . . . ?
C16 C17 C18 C19 175.7(5) . . . . ?
C23 C18 C19 C20 -0.8(8) . . . . ?
C17 C18 C19 C20 -179.2(5) . . . . ?
C18 C19 C20 C21 1.3(9) . . . . ?
C24 O2 C21 C22 -1.0(8) . . . . ?
C24 O2 C21 C20 177.9(6) . . . . ?
C19 C20 C21 C22 -1.6(10) . . . . ?
C19 C20 C21 O2 179.4(5) . . . . ?
O2 C21 C22 C23 -179.8(5) . . . . ?
C20 C21 C22 C23 1.2(9) . . . . ?
C19 C18 C23 C22 0.5(8) . . . . ?
C17 C18 C23 C22 178.8(4) . . . . ?
C21 C22 C23 C18 -0.7(8) . . . . ?

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_X
_database_code_depnum_ccdc_archive 'CCDC 1063124'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H18 O2'
_chemical_formula_sum            'C26 H18 O2'
_chemical_formula_weight         362.40

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.343(2)
_cell_length_b                   7.9890(16)
_cell_length_c                   21.559(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.06(3)
_cell_angle_gamma                90
_cell_volume                     1895.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3477
_cell_measurement_theta_min      1.851
_cell_measurement_theta_max      25.370

_exptl_crystal_description       rhombohedral
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   'North et al., 1968'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3477
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.851
_diffrn_reflns_theta_max         25.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3477
_reflns_number_gt                1705
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'WinGX publication routines (Farrugia, 1998)'
_computing_structure_solution    ??
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1998)'
_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)+(0.0790P)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_number_reflns         3477
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1264
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1686
_refine_ls_wR_factor_gt          0.1387
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
C1 C 0.0796(2) 0.3043(4) 0.15528(13) 0.0694(7) Uani 1 1 d . . . . .
O1 O 0.29582(18) -0.1269(3) 0.16232(9) 0.0935(7) Uani 1 1 d . . . . .
O2 O 0.43171(18) -0.4979(3) 0.42813(9) 0.0885(6) Uani 1 1 d . . . . .
C2 C 0.1067(3) 0.4266(4) 0.20362(14) 0.0823(9) Uani 1 1 d . . . . .
H2A H 0.1630 0.4012 0.2416 0.099 Uiso 1 1 calc R U . . .
C3 C 0.0537(3) 0.5808(5) 0.19687(16) 0.0856(9) Uani 1 1 d . . . . .
H3A H 0.0748 0.6580 0.2300 0.103 Uiso 1 1 calc R U . . .
C4 C -0.0325(3) 0.6248(4) 0.14045(15) 0.0744(8) Uani 1 1 d . . . . .
C5 C -0.0628(2) 0.5029(4) 0.09094(13) 0.0636(7) Uani 1 1 d . . . . .
C6 C -0.0078(2) 0.3429(3) 0.09784(12) 0.0593(7) Uani 1 1 d . . . . .
C7 C -0.0876(3) 0.7868(4) 0.13023(18) 0.0880(10) Uani 1 1 d . . . . .
H7A H -0.0656 0.8673 0.1621 0.106 Uiso 1 1 calc R U . . .
C8 C -0.1690(3) 0.8262(4) 0.0768(2) 0.0951(11) Uani 1 1 d . . . . .
H8A H -0.2031 0.9327 0.0722 0.114 Uiso 1 1 calc R U . . .
C9 C -0.2049(3) 0.7071(4) 0.02622(18) 0.0812(9) Uani 1 1 d . . . . .
C10 C -0.1516(2) 0.5458(4) 0.03359(14) 0.0641(7) Uani 1 1 d . . . . .
C11 C -0.2910(3) 0.7452(4) -0.0312(2) 0.0938(10) Uani 1 1 d . . . . .
H11A H -0.3265 0.8508 -0.0368 0.113 Uiso 1 1 calc R U . . .
C12 C -0.3225(3) 0.6282(5) -0.07855(17) 0.0974(11) Uani 1 1 d . . . . .
H12A H -0.3808 0.6552 -0.1156 0.117 Uiso 1 1 calc R U . . .
C13 C -0.2708(3) 0.4731(4) -0.07297(14) 0.0806(9) Uani 1 1 d . . . . .
H13A H -0.2927 0.3969 -0.1064 0.097 Uiso 1 1 calc R U . . .
C14 C -0.1840(2) 0.4278(4) -0.01648(13) 0.0648(7) Uani 1 1 d . . . . .
C15 C -0.1281(2) 0.2687(3) -0.00835(13) 0.0667(7) Uani 1 1 d . . . . .
H15A H -0.1499 0.1899 -0.0409 0.080 Uiso 1 1 calc R U . . .
C16 C -0.0427(2) 0.2273(3) 0.04613(13) 0.0655(7) Uani 1 1 d . . . . .
H16A H -0.0068 0.1220 0.0495 0.079 Uiso 1 1 calc R U . . .
C17 C 0.1470(2) 0.1470(4) 0.16263(13) 0.0727(8) Uani 1 1 d . . . . .
H17A H 0.1469 0.0907 0.1249 0.087 Uiso 1 1 calc R U . . .
C18 C 0.2085(3) 0.0735(4) 0.21590(14) 0.0786(8) Uani 1 1 d . . . . .
H18A H 0.2081 0.1204 0.2553 0.094 Uiso 1 1 calc R U . . .
C19 C 0.2769(2) -0.0803(4) 0.21337(13) 0.0721(8) Uani 1 1 d . . . . .
C20 C 0.3212(2) -0.1845(4) 0.27129(12) 0.0673(8) Uani 1 1 d . . . . .
C21 C 0.3886(2) -0.3265(4) 0.26709(13) 0.0803(9) Uani 1 1 d . . . . .
H21A H 0.4079 -0.3500 0.2285 0.096 Uiso 1 1 calc R U . . .
C22 C 0.4282(2) -0.4345(4) 0.31760(14) 0.0782(8) Uani 1 1 d . . . . .
H22A H 0.4739 -0.5286 0.3133 0.094 Uiso 1 1 calc R U . . .
C23 C 0.3988(2) -0.4005(4) 0.37516(13) 0.0713(8) Uani 1 1 d . . . . .
C24 C 0.3320(3) -0.2588(4) 0.38037(14) 0.0840(9) Uani 1 1 d . . . . .
H24A H 0.3123 -0.2356 0.4189 0.101 Uiso 1 1 calc R U . . .
C25 C 0.2947(2) -0.1527(4) 0.32997(13) 0.0778(8) Uani 1 1 d . . . . .
H25A H 0.2508 -0.0573 0.3348 0.093 Uiso 1 1 calc R U . . .
C26 C 0.4894(3) -0.6538(4) 0.42361(15) 0.0999(11) Uani 1 1 d . . . . .
H26A H 0.5072 -0.7084 0.4645 0.150 Uiso 1 1 calc R U . . .
H26B H 0.4363 -0.7232 0.3926 0.150 Uiso 1 1 calc R U . . .
H26C H 0.5635 -0.6350 0.4107 0.150 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
C1 C2 1.407(4) . ?
C1 C6 1.420(3) . ?
C1 C17 1.459(4) . ?
O1 C19 1.229(3) . ?
O2 C23 1.358(3) . ?
O2 C26 1.421(3) . ?
C2 C3 1.363(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.408(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.424(4) . ?
C4 C7 1.431(4) . ?
C5 C6 1.414(4) . ?
C5 C10 1.434(4) . ?
C6 C16 1.427(3) . ?
C7 C8 1.327(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.430(4) . ?
C8 H8A 0.9300 . ?
C9 C11 1.410(4) . ?
C9 C10 1.416(4) . ?
C10 C14 1.413(4) . ?
C11 C12 1.367(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.364(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.415(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.413(3) . ?
C15 C16 1.369(3) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 C18 1.327(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.461(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.483(4) . ?
C20 C21 1.384(4) . ?
C20 C25 1.393(3) . ?
C21 C22 1.377(4) . ?
C21 H21A 0.9300 . ?
C22 C23 1.388(4) . ?
C22 H22A 0.9300 . ?
C23 C24 1.381(4) . ?
C24 C25 1.362(4) . ?
C24 H24A 0.9300 . ?
C25 H25A 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
C2 C1 C6 118.4(3) . . ?
C2 C1 C17 120.2(3) . . ?
C6 C1 C17 121.2(3) . . ?
C23 O2 C26 118.8(2) . . ?
C3 C2 C1 122.5(3) . . ?
C3 C2 H2A 118.8 . . ?
C1 C2 H2A 118.8 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C3 C4 C5 117.9(3) . . ?
C3 C4 C7 123.0(3) . . ?
C5 C4 C7 119.1(3) . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 C10 120.4(3) . . ?
C4 C5 C10 118.3(3) . . ?
C5 C6 C1 119.0(3) . . ?
C5 C6 C16 118.1(2) . . ?
C1 C6 C16 122.9(3) . . ?
C8 C7 C4 122.3(3) . . ?
C8 C7 H7A 118.9 . . ?
C4 C7 H7A 118.9 . . ?
C7 C8 C9 120.9(3) . . ?
C7 C8 H8A 119.6 . . ?
C9 C8 H8A 119.6 . . ?
C11 C9 C10 118.8(3) . . ?
C11 C9 C8 122.2(4) . . ?
C10 C9 C8 119.0(3) . . ?
C14 C10 C9 119.8(3) . . ?
C14 C10 C5 119.8(3) . . ?
C9 C10 C5 120.4(3) . . ?
C12 C11 C9 120.5(3) . . ?
C12 C11 H11A 119.7 . . ?
C9 C11 H11A 119.7 . . ?
C13 C12 C11 121.8(3) . . ?
C13 C12 H12A 119.1 . . ?
C11 C12 H12A 119.1 . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H13A 119.9 . . ?
C14 C13 H13A 119.9 . . ?
C15 C14 C10 118.7(3) . . ?
C15 C14 C13 122.3(3) . . ?
C10 C14 C13 119.0(3) . . ?
C16 C15 C14 121.8(3) . . ?
C16 C15 H15A 119.1 . . ?
C14 C15 H15A 119.1 . . ?
C15 C16 C6 121.2(3) . . ?
C15 C16 H16A 119.4 . . ?
C6 C16 H16A 119.4 . . ?
C18 C17 C1 128.8(3) . . ?
C18 C17 H17A 115.6 . . ?
C1 C17 H17A 115.6 . . ?
C17 C18 C19 120.8(3) . . ?
C17 C18 H18A 119.6 . . ?
C19 C18 H18A 119.6 . . ?
O1 C19 C18 119.9(3) . . ?
O1 C19 C20 119.2(3) . . ?
C18 C19 C20 121.0(3) . . ?
C21 C20 C25 117.0(3) . . ?
C21 C20 C19 119.0(2) . . ?
C25 C20 C19 124.0(3) . . ?
C22 C21 C20 122.8(3) . . ?
C22 C21 H21A 118.6 . . ?
C20 C21 H21A 118.6 . . ?
C21 C22 C23 118.7(3) . . ?
C21 C22 H22A 120.6 . . ?
C23 C22 H22A 120.6 . . ?
O2 C23 C24 116.5(3) . . ?
O2 C23 C22 124.2(3) . . ?
C24 C23 C22 119.3(3) . . ?
C25 C24 C23 121.0(3) . . ?
C25 C24 H24A 119.5 . . ?
C23 C24 H24A 119.5 . . ?
C24 C25 C20 121.2(3) . . ?
C24 C25 H25A 119.4 . . ?
C20 C25 H25A 119.4 . . ?
O2 C26 H26A 109.5 . . ?
O2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
C6 C1 C2 C3 -1.1(4) . . . . ?
C17 C1 C2 C3 174.4(3) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C2 C3 C4 C7 -177.8(3) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C7 C4 C5 C6 177.9(2) . . . . ?
C3 C4 C5 C10 179.3(2) . . . . ?
C7 C4 C5 C10 -2.6(4) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C10 C5 C6 C1 -179.9(2) . . . . ?
C4 C5 C6 C16 -180.0(2) . . . . ?
C10 C5 C6 C16 0.5(3) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C17 C1 C6 C5 -174.4(2) . . . . ?
C2 C1 C6 C16 -179.4(2) . . . . ?
C17 C1 C6 C16 5.2(4) . . . . ?
C3 C4 C7 C8 -179.9(3) . . . . ?
C5 C4 C7 C8 2.1(4) . . . . ?
C4 C7 C8 C9 -0.5(5) . . . . ?
C7 C8 C9 C11 -179.9(3) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
C11 C9 C10 C14 0.8(4) . . . . ?
C8 C9 C10 C14 -178.6(2) . . . . ?
C11 C9 C10 C5 179.3(2) . . . . ?
C8 C9 C10 C5 0.0(4) . . . . ?
C6 C5 C10 C14 -0.3(3) . . . . ?
C4 C5 C10 C14 -179.9(2) . . . . ?
C6 C5 C10 C9 -178.8(2) . . . . ?
C4 C5 C10 C9 1.6(3) . . . . ?
C10 C9 C11 C12 0.3(4) . . . . ?
C8 C9 C11 C12 179.6(3) . . . . ?
C9 C11 C12 C13 -1.4(5) . . . . ?
C11 C12 C13 C14 1.4(5) . . . . ?
C9 C10 C14 C15 179.0(2) . . . . ?
C5 C10 C14 C15 0.5(3) . . . . ?
C9 C10 C14 C13 -0.8(4) . . . . ?
C5 C10 C14 C13 -179.3(2) . . . . ?
C12 C13 C14 C15 179.9(3) . . . . ?
C12 C13 C14 C10 -0.3(4) . . . . ?
C10 C14 C15 C16 -0.9(4) . . . . ?
C13 C14 C15 C16 178.9(2) . . . . ?
C14 C15 C16 C6 1.1(4) . . . . ?
C5 C6 C16 C15 -0.9(4) . . . . ?
C1 C6 C16 C15 179.5(2) . . . . ?
C2 C1 C17 C18 22.4(4) . . . . ?
C6 C1 C17 C18 -162.3(3) . . . . ?
C1 C17 C18 C19 -176.2(2) . . . . ?
C17 C18 C19 O1 12.8(4) . . . . ?
C17 C18 C19 C20 -165.4(3) . . . . ?
O1 C19 C20 C21 3.6(4) . . . . ?
C18 C19 C20 C21 -178.2(3) . . . . ?
O1 C19 C20 C25 -173.4(3) . . . . ?
C18 C19 C20 C25 4.8(4) . . . . ?
C25 C20 C21 C22 0.4(4) . . . . ?
C19 C20 C21 C22 -176.8(3) . . . . ?
C20 C21 C22 C23 0.5(4) . . . . ?
C26 O2 C23 C24 173.5(3) . . . . ?
C26 O2 C23 C22 -6.7(4) . . . . ?
C21 C22 C23 O2 179.5(3) . . . . ?
C21 C22 C23 C24 -0.7(4) . . . . ?
O2 C23 C24 C25 179.9(3) . . . . ?
C22 C23 C24 C25 0.1(4) . . . . ?
C23 C24 C25 C20 0.9(4) . . . . ?
C21 C20 C25 C24 -1.1(4) . . . . ?
C19 C20 C25 C24 176.0(3) . . . . ?

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_X
_database_code_depnum_ccdc_archive 'CCDC 1063125'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H18 O2'
_chemical_formula_sum            'C26 H18 O2'
_chemical_formula_weight         362.40

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   29.981(6)
_cell_length_b                   5.7400(11)
_cell_length_c                   21.533(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.25(3)
_cell_angle_gamma                90
_cell_volume                     3704.8(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3381
_cell_measurement_theta_min      1.359
_cell_measurement_theta_max      25.371

_exptl_crystal_description       rodlike
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3382
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.359
_diffrn_reflns_theta_max         25.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3381
_reflns_number_gt                1439
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'WinGX publication routines (Farrugia, 1998)'
_computing_structure_solution    ??
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1998)'
_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)+(0.0600P)²+5.0000P] 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_number_reflns         3382
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1849
_refine_ls_R_factor_gt           0.0871
_refine_ls_wR_factor_ref         0.2040
_refine_ls_wR_factor_gt          0.1647
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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 0.76229(9) 0.7787(6) 0.34056(14) 0.0817(10) Uani 1 1 d . . . . .
O2 O 0.91170(12) 0.5034(7) 0.1558(2) 0.1171(15) Uani 1 1 d . . . . .
C1 C 0.75874(17) 0.9635(9) 0.3835(3) 0.109(2) Uani 1 1 d . . . . .
H1A H 0.7326 0.9415 0.4079 0.164 Uiso 1 1 calc R U . . .
H1B H 0.7847 0.9659 0.4103 0.164 Uiso 1 1 calc R U . . .
H1C H 0.7564 1.1085 0.3615 0.164 Uiso 1 1 calc R U . . .
C2 C 0.79738(13) 0.7763(8) 0.30103(18) 0.0542(11) Uani 1 1 d . . . . .
C3 C 0.82915(14) 0.9517(8) 0.2994(2) 0.0686(13) Uani 1 1 d . . . . .
H3A H 0.8266 1.0825 0.3246 0.082 Uiso 1 1 calc R U . . .
C4 C 0.86497(14) 0.9292(8) 0.2595(2) 0.0690(13) Uani 1 1 d . . . . .
H4A H 0.8863 1.0467 0.2581 0.083 Uiso 1 1 calc R U . . .
C5 C 0.86926(12) 0.7380(8) 0.22236(19) 0.0585(11) Uani 1 1 d . . . . .
C6 C 0.83659(13) 0.5593(8) 0.22472(18) 0.0615(12) Uani 1 1 d . . . . .
H6A H 0.8390 0.4265 0.2003 0.074 Uiso 1 1 calc R U . . .
C7 C 0.80132(13) 0.5865(8) 0.26387(19) 0.0581(11) Uani 1 1 d . . . . .
H7A H 0.7795 0.4714 0.2649 0.070 Uiso 1 1 calc R U . . .
C8 C 0.90725(15) 0.6975(9) 0.1795(2) 0.0728(14) Uani 1 1 d . . . . .
C9 C 0.94062(14) 0.8800(8) 0.1719(2) 0.0655(13) Uani 1 1 d . . . . .
H9A H 0.9376 1.0198 0.1933 0.079 Uiso 1 1 calc R U . . .
C10 C 0.97520(13) 0.8508(8) 0.13535(19) 0.0654(13) Uani 1 1 d . . . . .
H10A H 0.9762 0.7118 0.1133 0.078 Uiso 1 1 calc R U . . .
C11 C 1.01186(13) 1.0130(9) 0.12600(18) 0.0600(12) Uani 1 1 d . . . . .
C12 C 1.01677(15) 1.2062(9) 0.1633(2) 0.0679(13) Uani 1 1 d . . . . .
H12A H 0.9952 1.2362 0.1926 0.081 Uiso 1 1 calc R U . . .
C13 C 1.05212(15) 1.3564(9) 0.1589(2) 0.0752(14) Uani 1 1 d . . . . .
H13A H 1.0546 1.4830 0.1857 0.090 Uiso 1 1 calc R U . . .
C14 C 1.08462(14) 1.3187(9) 0.1138(2) 0.0648(13) Uani 1 1 d . . . . .
C15 C 1.07966(13) 1.1314(8) 0.07377(18) 0.0554(11) Uani 1 1 d . . . . .
C16 C 1.12256(16) 1.4711(10) 0.1091(2) 0.0874(16) Uani 1 1 d . . . . .
H16A H 1.1261 1.5952 0.1365 0.105 Uiso 1 1 calc R U . . .
C17 C 1.15250(17) 1.4337(10) 0.0654(3) 0.0909(17) Uani 1 1 d . . . . .
H17A H 1.1766 1.5348 0.0630 0.109 Uiso 1 1 calc R U . . .
C18 C 1.14923(14) 1.2467(10) 0.0226(2) 0.0714(14) Uani 1 1 d . . . . .
C19 C 1.11185(13) 1.0931(9) 0.0256(2) 0.0648(13) Uani 1 1 d . . . . .
C20 C 1.18023(16) 1.2056(13) -0.0235(3) 0.102(2) Uani 1 1 d . . . . .
H20A H 1.2052 1.3008 -0.0260 0.123 Uiso 1 1 calc R U . . .
C21 C 1.17439(19) 1.0244(13) -0.0657(3) 0.106(2) Uani 1 1 d . . . . .
H21A H 1.1952 1.0030 -0.0965 0.127 Uiso 1 1 calc R U . . .
C22 C 1.13852(15) 0.8763(11) -0.0628(2) 0.0882(17) Uani 1 1 d . . . . .
H22A H 1.1353 0.7550 -0.0912 0.106 Uiso 1 1 calc R U . . .
C23 C 1.10676(15) 0.9088(10) -0.0169(2) 0.0703(13) Uani 1 1 d . . . . .
C24 C 1.06869(14) 0.7602(9) -0.0120(2) 0.0707(13) Uani 1 1 d . . . . .
H24A H 1.0648 0.6392 -0.0404 0.085 Uiso 1 1 calc R U . . .
C25 C 1.03829(14) 0.7903(9) 0.03240(19) 0.0675(13) Uani 1 1 d . . . . .
H25A H 1.0141 0.6892 0.0342 0.081 Uiso 1 1 calc R U . . .
C26 C 1.04239(13) 0.9746(8) 0.07693(19) 0.0602(12) Uani 1 1 d . . . . .


_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 C2 1.368(4) . ?
O1 C1 1.412(5) . ?
O2 C8 1.234(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.359(5) . ?
C2 C3 1.387(5) . ?
C3 C4 1.397(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.365(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.420(5) . ?
C5 C8 1.500(5) . ?
C6 C7 1.376(5) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C9 1.460(6) . ?
C9 C10 1.326(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.458(6) . ?
C10 H10A 0.9300 . ?
C11 C12 1.375(6) . ?
C11 C26 1.430(5) . ?
C12 C13 1.371(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.407(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.385(6) . ?
C14 C16 1.440(6) . ?
C15 C26 1.438(5) . ?
C15 C19 1.449(6) . ?
C16 C17 1.332(6) . ?
C16 H16A 0.9300 . ?
C17 C18 1.418(7) . ?
C17 H17A 0.9300 . ?
C18 C20 1.393(7) . ?
C18 C19 1.429(6) . ?
C19 C23 1.405(6) . ?
C20 C21 1.390(8) . ?
C20 H20A 0.9300 . ?
C21 C22 1.373(7) . ?
C21 H21A 0.9300 . ?
C22 C23 1.400(6) . ?
C22 H22A 0.9300 . ?
C23 C24 1.430(6) . ?
C24 C25 1.347(5) . ?
C24 H24A 0.9300 . ?
C25 C26 1.431(6) . ?
C25 H25A 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
C2 O1 C1 119.0(4) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 O1 116.9(4) . . ?
C7 C2 C3 119.9(4) . . ?
O1 C2 C3 123.1(4) . . ?
C2 C3 C4 119.1(4) . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 H3A 120.5 . . ?
C5 C4 C3 121.2(4) . . ?
C5 C4 H4A 119.4 . . ?
C3 C4 H4A 119.4 . . ?
C4 C5 C6 119.1(4) . . ?
C4 C5 C8 124.6(4) . . ?
C6 C5 C8 116.3(4) . . ?
C7 C6 C5 118.7(4) . . ?
C7 C6 H6A 120.7 . . ?
C5 C6 H6A 120.7 . . ?
C2 C7 C6 122.0(4) . . ?
C2 C7 H7A 119.0 . . ?
C6 C7 H7A 119.0 . . ?
O2 C8 C9 121.4(4) . . ?
O2 C8 C5 119.0(4) . . ?
C9 C8 C5 119.3(4) . . ?
C10 C9 C8 121.5(4) . . ?
C10 C9 H9A 119.3 . . ?
C8 C9 H9A 119.3 . . ?
C9 C10 C11 127.1(4) . . ?
C9 C10 H10A 116.5 . . ?
C11 C10 H10A 116.5 . . ?
C12 C11 C26 119.6(4) . . ?
C12 C11 C10 120.4(4) . . ?
C26 C11 C10 120.0(4) . . ?
C13 C12 C11 122.7(4) . . ?
C13 C12 H12A 118.7 . . ?
C11 C12 H12A 118.7 . . ?
C12 C13 C14 119.9(5) . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C15 C14 C13 118.8(4) . . ?
C15 C14 C16 120.1(4) . . ?
C13 C14 C16 121.0(5) . . ?
C14 C15 C26 122.0(4) . . ?
C14 C15 C19 120.0(4) . . ?
C26 C15 C19 118.0(4) . . ?
C17 C16 C14 119.8(5) . . ?
C17 C16 H16A 120.1 . . ?
C14 C16 H16A 120.1 . . ?
C16 C17 C18 123.0(5) . . ?
C16 C17 H17A 118.5 . . ?
C18 C17 H17A 118.5 . . ?
C20 C18 C17 123.6(5) . . ?
C20 C18 C19 117.6(6) . . ?
C17 C18 C19 118.7(5) . . ?
C23 C19 C18 120.6(4) . . ?
C23 C19 C15 121.1(4) . . ?
C18 C19 C15 118.3(5) . . ?
C21 C20 C18 121.0(5) . . ?
C21 C20 H20A 119.5 . . ?
C18 C20 H20A 119.5 . . ?
C22 C21 C20 121.4(5) . . ?
C22 C21 H21A 119.3 . . ?
C20 C21 H21A 119.3 . . ?
C21 C22 C23 119.7(6) . . ?
C21 C22 H22A 120.2 . . ?
C23 C22 H22A 120.2 . . ?
C22 C23 C19 119.6(5) . . ?
C22 C23 C24 121.9(5) . . ?
C19 C23 C24 118.5(4) . . ?
C25 C24 C23 121.9(5) . . ?
C25 C24 H24A 119.0 . . ?
C23 C24 H24A 119.0 . . ?
C24 C25 C26 121.4(4) . . ?
C24 C25 H25A 119.3 . . ?
C26 C25 H25A 119.3 . . ?
C11 C26 C25 124.2(4) . . ?
C11 C26 C15 116.7(4) . . ?
C25 C26 C15 119.1(4) . . ?

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
C1 O1 C2 C7 175.1(4) . . . . ?
C1 O1 C2 C3 -2.3(6) . . . . ?
C7 C2 C3 C4 -0.2(6) . . . . ?
O1 C2 C3 C4 177.1(4) . . . . ?
C2 C3 C4 C5 -0.3(7) . . . . ?
C3 C4 C5 C6 0.0(7) . . . . ?
C3 C4 C5 C8 -178.3(4) . . . . ?
C4 C5 C6 C7 0.8(6) . . . . ?
C8 C5 C6 C7 179.2(4) . . . . ?
O1 C2 C7 C6 -176.5(4) . . . . ?
C3 C2 C7 C6 1.0(6) . . . . ?
C5 C6 C7 C2 -1.3(6) . . . . ?
C4 C5 C8 O2 168.3(5) . . . . ?
C6 C5 C8 O2 -10.0(7) . . . . ?
C4 C5 C8 C9 -5.4(7) . . . . ?
C6 C5 C8 C9 176.4(4) . . . . ?
O2 C8 C9 C10 5.4(8) . . . . ?
C5 C8 C9 C10 178.9(4) . . . . ?
C8 C9 C10 C11 -176.8(4) . . . . ?
C9 C10 C11 C12 9.6(7) . . . . ?
C9 C10 C11 C26 -168.9(4) . . . . ?
C26 C11 C12 C13 -5.5(6) . . . . ?
C10 C11 C12 C13 176.0(4) . . . . ?
C11 C12 C13 C14 1.6(7) . . . . ?
C12 C13 C14 C15 1.2(6) . . . . ?
C12 C13 C14 C16 -178.7(4) . . . . ?
C13 C14 C15 C26 -0.1(6) . . . . ?
C16 C14 C15 C26 179.8(4) . . . . ?
C13 C14 C15 C19 178.0(4) . . . . ?
C16 C14 C15 C19 -2.2(6) . . . . ?
C15 C14 C16 C17 1.1(7) . . . . ?
C13 C14 C16 C17 -179.0(5) . . . . ?
C14 C16 C17 C18 -0.5(8) . . . . ?
C16 C17 C18 C20 179.9(5) . . . . ?
C16 C17 C18 C19 1.0(8) . . . . ?
C20 C18 C19 C23 -0.5(6) . . . . ?
C17 C18 C19 C23 178.5(4) . . . . ?
C20 C18 C19 C15 179.1(4) . . . . ?
C17 C18 C19 C15 -1.9(6) . . . . ?
C14 C15 C19 C23 -177.9(4) . . . . ?
C26 C15 C19 C23 0.2(6) . . . . ?
C14 C15 C19 C18 2.5(6) . . . . ?
C26 C15 C19 C18 -179.4(4) . . . . ?
C17 C18 C20 C21 -177.6(5) . . . . ?
C19 C18 C20 C21 1.4(8) . . . . ?
C18 C20 C21 C22 -1.5(9) . . . . ?
C20 C21 C22 C23 0.7(8) . . . . ?
C21 C22 C23 C19 0.2(7) . . . . ?
C21 C22 C23 C24 179.7(5) . . . . ?
C18 C19 C23 C22 -0.3(7) . . . . ?
C15 C19 C23 C22 -179.9(4) . . . . ?
C18 C19 C23 C24 -179.8(4) . . . . ?
C15 C19 C23 C24 0.6(6) . . . . ?
C22 C23 C24 C25 179.5(5) . . . . ?
C19 C23 C24 C25 -1.0(7) . . . . ?
C23 C24 C25 C26 0.5(7) . . . . ?
C12 C11 C26 C25 -174.7(4) . . . . ?
C10 C11 C26 C25 3.8(6) . . . . ?
C12 C11 C26 C15 6.3(6) . . . . ?
C10 C11 C26 C15 -175.2(4) . . . . ?
C24 C25 C26 C11 -178.6(4) . . . . ?
C24 C25 C26 C15 0.4(6) . . . . ?
C14 C15 C26 C11 -3.6(6) . . . . ?
C19 C15 C26 C11 178.3(4) . . . . ?
C14 C15 C26 C25 177.3(4) . . . . ?
C19 C15 C26 C25 -0.7(5) . . . . ?

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_X
_database_code_depnum_ccdc_archive 'CCDC 1063126'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H16 O'
_chemical_formula_sum            'C23 H16 O'
_chemical_formula_weight         308.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   16.727(3)
_cell_length_b                   5.6410(11)
_cell_length_c                   18.544(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.35(3)
_cell_angle_gamma                90
_cell_volume                     1650.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3045
_cell_measurement_theta_min      1.423
_cell_measurement_theta_max      25.387

_exptl_crystal_description       rodlike
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3148
_diffrn_reflns_av_unetI/netI     0.0681
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.423
_diffrn_reflns_theta_max         25.387
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3045
_reflns_number_gt                1282
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'WinGX publication routines (Farrugia, 1998)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1998)'
_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)+(0.0680P)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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0118(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3040
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1635
_refine_ls_R_factor_gt           0.0675
_refine_ls_wR_factor_ref         0.1823
_refine_ls_wR_factor_gt          0.1412
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
O O 0.39362(14) 0.9800(4) 0.15277(15) 0.0896(9) Uani 1 1 d . . . . .
C1 C 0.5803(2) 0.8475(6) 0.2823(3) 0.0742(10) Uani 1 1 d . . . . .
C2 C 0.5530(2) 0.7422(8) 0.3401(3) 0.0976(13) Uani 1 1 d . . . . .
H2A H 0.5164 0.6130 0.3273 0.117 Uiso 1 1 calc R U . . .
C3 C 0.5782(3) 0.8232(11) 0.4122(3) 0.1213(17) Uani 1 1 d . . . . .
H3A H 0.5600 0.7487 0.4487 0.146 Uiso 1 1 calc R U . . .
C4 C 0.6325(3) 1.0215(12) 0.4326(3) 0.1223(18) Uani 1 1 d . . . . .
H4A H 0.6491 1.0785 0.4824 0.147 Uiso 1 1 calc R U . . .
C5 C 0.6608(3) 1.1302(9) 0.3803(3) 0.1065(15) Uani 1 1 d . . . . .
H5A H 0.6967 1.2604 0.3947 0.128 Uiso 1 1 calc R U . . .
C6 C 0.6358(2) 1.0454(7) 0.3034(3) 0.0805(11) Uani 1 1 d . . . . .
C7 C 0.6653(2) 1.1471(7) 0.2487(3) 0.0916(13) Uani 1 1 d . . . . .
H7A H 0.7007 1.2786 0.2620 0.110 Uiso 1 1 calc R U . . .
C8 C 0.6438(2) 1.0593(7) 0.1755(3) 0.0824(11) Uani 1 1 d . . . . .
C9 C 0.6752(3) 1.1625(8) 0.1195(4) 0.1059(15) Uani 1 1 d . . . . .
H9A H 0.7108 1.2937 0.1324 0.127 Uiso 1 1 calc R U . . .
C10 C 0.6541(3) 1.0725(11) 0.0490(4) 0.1191(17) Uani 1 1 d . . . . .
H10A H 0.6743 1.1443 0.0133 0.143 Uiso 1 1 calc R U . . .
C11 C 0.6017(3) 0.8714(10) 0.0276(3) 0.1123(15) Uani 1 1 d . . . . .
H11A H 0.5892 0.8080 -0.0212 0.135 Uiso 1 1 calc R U . . .
C12 C 0.5695(2) 0.7701(8) 0.0787(3) 0.0959(13) Uani 1 1 d . . . . .
H12A H 0.5339 0.6395 0.0638 0.115 Uiso 1 1 calc R U . . .
C13 C 0.5890(2) 0.8593(7) 0.1546(3) 0.0753(11) Uani 1 1 d . . . . .
C14 C 0.5557(2) 0.7600(6) 0.2076(3) 0.0730(10) Uani 1 1 d . . . . .
C15 C 0.4958(2) 0.5587(6) 0.1851(2) 0.0821(11) Uani 1 1 d . . . . .
H15A H 0.5198 0.4096 0.1861 0.099 Uiso 1 1 calc R U . . .
C16 C 0.4121(2) 0.5662(5) 0.16373(19) 0.0725(10) Uani 1 1 d . . . . .
H16A H 0.3830 0.4230 0.1540 0.087 Uiso 1 1 calc R U . . .
C17 C 0.3619(2) 0.7849(6) 0.15432(18) 0.0646(9) Uani 1 1 d . . . . .
C18 C 0.2708(2) 0.7659(6) 0.14601(17) 0.0610(9) Uani 1 1 d . . . . .
C19 C 0.2178(2) 0.9509(6) 0.1115(2) 0.0782(11) Uani 1 1 d . . . . .
H19A H 0.2393 1.0809 0.0931 0.094 Uiso 1 1 calc R U . . .
C20 C 0.1329(3) 0.9435(7) 0.1042(2) 0.0950(13) Uani 1 1 d . . . . .
H20A H 0.0973 1.0676 0.0805 0.114 Uiso 1 1 calc R U . . .
C21 C 0.1012(3) 0.7538(8) 0.1320(2) 0.0937(13) Uani 1 1 d . . . . .
H21A H 0.0441 0.7493 0.1270 0.112 Uiso 1 1 calc R U . . .
C22 C 0.1534(3) 0.5698(7) 0.1672(2) 0.0873(12) Uani 1 1 d . . . . .
H22A H 0.1320 0.4420 0.1867 0.105 Uiso 1 1 calc R U . . .
C23 C 0.2378(2) 0.5761(6) 0.17350(18) 0.0735(10) Uani 1 1 d . . . . .
H23A H 0.2730 0.4506 0.1966 0.088 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
O C17 1.226(3) . ?
C1 C14 1.398(5) . ?
C1 C6 1.421(5) . ?
C1 C2 1.426(5) . ?
C2 C3 1.342(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.411(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.358(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.430(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.390(5) . ?
C7 C8 1.377(5) . ?
C7 H7A 0.9300 . ?
C8 C13 1.423(5) . ?
C8 C9 1.434(5) . ?
C9 C10 1.336(6) . ?
C9 H9A 0.9300 . ?
C10 C11 1.407(6) . ?
C10 H10A 0.9300 . ?
C11 C12 1.362(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.427(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.398(5) . ?
C14 C15 1.479(5) . ?
C15 C16 1.324(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.469(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.485(4) . ?
C18 C23 1.377(4) . ?
C18 C19 1.381(4) . ?
C19 C20 1.381(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.368(5) . ?
C20 H20A 0.9300 . ?
C21 C22 1.374(5) . ?
C21 H21A 0.9300 . ?
C22 C23 1.378(5) . ?
C22 H22A 0.9300 . ?
C23 H23A 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
C14 C1 C6 120.1(4) . . ?
C14 C1 C2 122.3(4) . . ?
C6 C1 C2 117.6(4) . . ?
C3 C2 C1 122.2(5) . . ?
C3 C2 H2A 118.9 . . ?
C1 C2 H2A 118.9 . . ?
C2 C3 C4 119.9(5) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C5 C4 C3 120.8(5) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 120.3(5) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C7 C6 C1 118.7(4) . . ?
C7 C6 C5 122.2(5) . . ?
C1 C6 C5 119.1(4) . . ?
C8 C7 C6 122.1(4) . . ?
C8 C7 H7A 118.9 . . ?
C6 C7 H7A 118.9 . . ?
C7 C8 C13 119.2(4) . . ?
C7 C8 C9 122.0(5) . . ?
C13 C8 C9 118.9(5) . . ?
C10 C9 C8 120.8(5) . . ?
C10 C9 H9A 119.6 . . ?
C8 C9 H9A 119.6 . . ?
C9 C10 C11 121.4(5) . . ?
C9 C10 H10A 119.3 . . ?
C11 C10 H10A 119.3 . . ?
C12 C11 C10 119.7(5) . . ?
C12 C11 H11A 120.2 . . ?
C10 C11 H11A 120.2 . . ?
C11 C12 C13 121.6(4) . . ?
C11 C12 H12A 119.2 . . ?
C13 C12 H12A 119.2 . . ?
C14 C13 C8 119.8(4) . . ?
C14 C13 C12 122.6(4) . . ?
C8 C13 C12 117.6(4) . . ?
C1 C14 C13 120.0(4) . . ?
C1 C14 C15 120.0(4) . . ?
C13 C14 C15 120.0(4) . . ?
C16 C15 C14 127.6(3) . . ?
C16 C15 H15A 116.2 . . ?
C14 C15 H15A 116.2 . . ?
C15 C16 C17 124.6(3) . . ?
C15 C16 H16A 117.7 . . ?
C17 C16 H16A 117.7 . . ?
O C17 C16 121.5(3) . . ?
O C17 C18 120.0(3) . . ?
C16 C17 C18 118.6(3) . . ?
C23 C18 C19 119.0(3) . . ?
C23 C18 C17 122.7(3) . . ?
C19 C18 C17 118.2(3) . . ?
C20 C19 C18 120.2(4) . . ?
C20 C19 H19A 119.9 . . ?
C18 C19 H19A 119.9 . . ?
C21 C20 C19 120.0(4) . . ?
C21 C20 H20A 120.0 . . ?
C19 C20 H20A 120.0 . . ?
C20 C21 C22 120.4(4) . . ?
C20 C21 H21A 119.8 . . ?
C22 C21 H21A 119.8 . . ?
C21 C22 C23 119.5(4) . . ?
C21 C22 H22A 120.3 . . ?
C23 C22 H22A 120.3 . . ?
C18 C23 C22 120.9(3) . . ?
C18 C23 H23A 119.6 . . ?
C22 C23 H23A 119.6 . . ?

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 178.4(4) . . . . ?
C6 C1 C2 C3 -0.4(5) . . . . ?
C1 C2 C3 C4 1.1(6) . . . . ?
C2 C3 C4 C5 -1.0(7) . . . . ?
C3 C4 C5 C6 0.2(7) . . . . ?
C14 C1 C6 C7 -0.6(5) . . . . ?
C2 C1 C6 C7 178.2(3) . . . . ?
C14 C1 C6 C5 -179.3(3) . . . . ?
C2 C1 C6 C5 -0.5(5) . . . . ?
C4 C5 C6 C7 -178.1(4) . . . . ?
C4 C5 C6 C1 0.6(6) . . . . ?
C1 C6 C7 C8 -1.3(5) . . . . ?
C5 C6 C7 C8 177.3(3) . . . . ?
C6 C7 C8 C13 0.6(5) . . . . ?
C6 C7 C8 C9 -179.1(3) . . . . ?
C7 C8 C9 C10 179.3(4) . . . . ?
C13 C8 C9 C10 -0.4(6) . . . . ?
C8 C9 C10 C11 -1.2(7) . . . . ?
C9 C10 C11 C12 2.2(7) . . . . ?
C10 C11 C12 C13 -1.5(6) . . . . ?
C7 C8 C13 C14 2.1(5) . . . . ?
C9 C8 C13 C14 -178.2(3) . . . . ?
C7 C8 C13 C12 -178.7(3) . . . . ?
C9 C8 C13 C12 1.0(5) . . . . ?
C11 C12 C13 C14 179.1(3) . . . . ?
C11 C12 C13 C8 -0.1(5) . . . . ?
C6 C1 C14 C13 3.3(5) . . . . ?
C2 C1 C14 C13 -175.5(3) . . . . ?
C6 C1 C14 C15 -178.1(3) . . . . ?
C2 C1 C14 C15 3.1(5) . . . . ?
C8 C13 C14 C1 -4.0(5) . . . . ?
C12 C13 C14 C1 176.9(3) . . . . ?
C8 C13 C14 C15 177.4(3) . . . . ?
C12 C13 C14 C15 -1.7(5) . . . . ?
C1 C14 C15 C16 82.9(5) . . . . ?
C13 C14 C15 C16 -98.5(5) . . . . ?
C14 C15 C16 C17 3.6(6) . . . . ?
C15 C16 C17 O 13.1(6) . . . . ?
C15 C16 C17 C18 -167.4(3) . . . . ?
O C17 C18 C23 -156.0(3) . . . . ?
C16 C17 C18 C23 24.4(5) . . . . ?
O C17 C18 C19 21.7(5) . . . . ?
C16 C17 C18 C19 -157.8(3) . . . . ?
C23 C18 C19 C20 -0.6(5) . . . . ?
C17 C18 C19 C20 -178.4(3) . . . . ?
C18 C19 C20 C21 0.7(6) . . . . ?
C19 C20 C21 C22 0.0(6) . . . . ?
C20 C21 C22 C23 -0.9(6) . . . . ?
C19 C18 C23 C22 -0.3(5) . . . . ?
C17 C18 C23 C22 177.4(3) . . . . ?
C21 C22 C23 C18 1.0(5) . . . . ?

_refine_diff_density_max         0.139
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_X
_database_code_depnum_ccdc_archive 'CCDC 1063127'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H16 O'
_chemical_formula_sum            'C23 H16 O'
_chemical_formula_weight         308.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   27.135(5)
_cell_length_b                   5.8300(12)
_cell_length_c                   20.776(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.03(3)
_cell_angle_gamma                90
_cell_volume                     3254.5(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2293
_cell_measurement_theta_min      1.516
_cell_measurement_theta_max      25.425

_exptl_crystal_description       rodlike
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   'North et al., 1968'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2993
_diffrn_reflns_av_unetI/netI     0.0905
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.516
_diffrn_reflns_theta_max         25.425
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2993
_reflns_number_gt                1229
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'WinGX publication routines (Farrugia, 1998)'
_computing_cell_refinement       'WinGX publication routines (Farrugia, 1998)'
_computing_data_reduction        'WinGX publication routines (Farrugia, 1998)'
_computing_structure_solution    ??
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1998)'
_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)+(0.0330P)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_number_reflns         2982
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1709
_refine_ls_R_factor_gt           0.0698
_refine_ls_wR_factor_ref         0.1422
_refine_ls_wR_factor_gt          0.1151
_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
O O 0.11567(9) 0.3488(4) 0.02677(12) 0.0764(9) Uani 1 1 d . . . . .
C1 C 0.04649(13) 0.3959(7) -0.08489(18) 0.0706(12) Uani 1 1 d . . . . .
H1A H 0.0650 0.2611 -0.0808 0.085 Uiso 1 1 calc R U . . .
C2 C 0.00730(15) 0.4188(8) -0.13476(19) 0.0837(14) Uani 1 1 d . . . . .
H2A H -0.0002 0.2998 -0.1643 0.100 Uiso 1 1 calc R U . . .
C3 C -0.02030(15) 0.6136(8) -0.14083(19) 0.0753(12) Uani 1 1 d . . . . .
H3A H -0.0467 0.6276 -0.1743 0.090 Uiso 1 1 calc R U . . .
C4 C -0.00914(15) 0.7900(7) -0.09749(19) 0.0816(13) Uani 1 1 d . . . . .
H4A H -0.0282 0.9232 -0.1015 0.098 Uiso 1 1 calc R U . . .
C5 C 0.03041(13) 0.7701(7) -0.04779(16) 0.0688(12) Uani 1 1 d . . . . .
H5A H 0.0381 0.8908 -0.0189 0.083 Uiso 1 1 calc R U . . .
C6 C 0.05820(12) 0.5734(6) -0.04115(15) 0.0460(9) Uani 1 1 d . . . . .
C7 C 0.09977(12) 0.5410(6) 0.01279(16) 0.0496(9) Uani 1 1 d . . . . .
C8 C 0.12123(13) 0.7439(6) 0.04855(16) 0.0625(11) Uani 1 1 d . . . . .
H8A H 0.1128 0.8873 0.0307 0.075 Uiso 1 1 calc R U . . .
C9 C 0.15035(13) 0.7371(6) 0.10194(17) 0.0642(11) Uani 1 1 d . . . . .
H9A H 0.1581 0.5925 0.1193 0.077 Uiso 1 1 calc R U . . .
C10 C 0.17336(13) 0.9360(6) 0.13971(17) 0.0532(10) Uani 1 1 d . . . . .
C11 C 0.15150(14) 1.0221(6) 0.19263(18) 0.0568(10) Uani 1 1 d . . . . .
C12 C 0.11051(15) 0.9115(7) 0.21502(19) 0.0725(12) Uani 1 1 d . . . . .
H12A H 0.0976 0.7783 0.1947 0.087 Uiso 1 1 calc R U . . .
C13 C 0.08992(16) 0.9982(10) 0.2659(2) 0.0932(16) Uani 1 1 d . . . . .
H13A H 0.0635 0.9221 0.2806 0.112 Uiso 1 1 calc R U . . .
C14 C 0.10845(19) 1.2030(10) 0.2967(2) 0.0896(16) Uani 1 1 d . . . . .
H14A H 0.0935 1.2628 0.3307 0.108 Uiso 1 1 calc R U . . .
C15 C 0.14756(17) 1.3126(8) 0.27725(19) 0.0781(13) Uani 1 1 d . . . . .
H15A H 0.1594 1.4468 0.2982 0.094 Uiso 1 1 calc R U . . .
C16 C 0.17104(14) 1.2257(7) 0.22516(17) 0.0576(10) Uani 1 1 d . . . . .
C17 C 0.21225(14) 1.3326(6) 0.20589(16) 0.0606(11) Uani 1 1 d . . . . .
H17A H 0.2246 1.4657 0.2270 0.073 Uiso 1 1 calc R U . . .
C18 C 0.23526(14) 1.2449(6) 0.15602(17) 0.0556(10) Uani 1 1 d . . . . .
C19 C 0.27745(16) 1.3547(7) 0.13645(19) 0.0729(12) Uani 1 1 d . . . . .
H19A H 0.2895 1.4886 0.1573 0.087 Uiso 1 1 calc R U . . .
C20 C 0.30038(16) 1.2682(8) 0.0881(2) 0.0824(14) Uani 1 1 d . . . . .
H20A H 0.3280 1.3420 0.0759 0.099 Uiso 1 1 calc R U . . .
C21 C 0.28213(16) 1.0649(8) 0.05599(19) 0.0834(14) Uani 1 1 d . . . . .
H21A H 0.2983 1.0043 0.0232 0.100 Uiso 1 1 calc R U . . .
C22 C 0.24177(15) 0.9586(7) 0.07241(18) 0.0706(12) Uani 1 1 d . . . . .
H22A H 0.2304 0.8258 0.0504 0.085 Uiso 1 1 calc R U . . .
C23 C 0.21580(14) 1.0433(6) 0.12257(16) 0.0525(9) Uani 1 1 d . . . . .


_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
O C7 1.221(4) . ?
C1 C2 1.384(4) . ?
C1 C6 1.385(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.357(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.372(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.386(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.369(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.487(4) . ?
C7 C8 1.473(4) . ?
C8 C9 1.269(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.487(4) . ?
C9 H9A 0.9300 . ?
C10 C23 1.400(4) . ?
C10 C11 1.412(5) . ?
C11 C12 1.419(5) . ?
C11 C16 1.431(5) . ?
C12 C13 1.360(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.414(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.348(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.423(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.387(4) . ?
C17 C18 1.380(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.420(5) . ?
C18 C23 1.429(4) . ?
C19 C20 1.351(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.415(5) . ?
C20 H20A 0.9300 . ?
C21 C22 1.343(5) . ?
C21 H21A 0.9300 . ?
C22 C23 1.425(4) . ?
C22 H22A 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
C2 C1 C6 120.1(4) . . ?
C2 C1 H1A 120.0 . . ?
C6 C1 H1A 120.0 . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C3 C4 C5 120.2(4) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C6 C5 C4 120.2(4) . . ?
C6 C5 H5A 119.9 . . ?
C4 C5 H5A 119.9 . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 C7 122.1(3) . . ?
C1 C6 C7 118.7(3) . . ?
O C7 C8 121.0(3) . . ?
O C7 C6 120.1(3) . . ?
C8 C7 C6 118.9(3) . . ?
C9 C8 C7 124.8(3) . . ?
C9 C8 H8A 117.6 . . ?
C7 C8 H8A 117.6 . . ?
C8 C9 C10 127.0(3) . . ?
C8 C9 H9A 116.5 . . ?
C10 C9 H9A 116.5 . . ?
C23 C10 C11 119.3(4) . . ?
C23 C10 C9 120.9(3) . . ?
C11 C10 C9 119.8(4) . . ?
C10 C11 C12 121.8(4) . . ?
C10 C11 C16 119.6(4) . . ?
C12 C11 C16 118.5(4) . . ?
C13 C12 C11 120.8(4) . . ?
C13 C12 H12A 119.6 . . ?
C11 C12 H12A 119.6 . . ?
C12 C13 C14 120.4(5) . . ?
C12 C13 H13A 119.8 . . ?
C14 C13 H13A 119.8 . . ?
C15 C14 C13 120.6(5) . . ?
C15 C14 H14A 119.7 . . ?
C13 C14 H14A 119.7 . . ?
C14 C15 C16 120.9(5) . . ?
C14 C15 H15A 119.5 . . ?
C16 C15 H15A 119.5 . . ?
C17 C16 C15 121.6(4) . . ?
C17 C16 C11 119.8(4) . . ?
C15 C16 C11 118.6(4) . . ?
C18 C17 C16 121.2(4) . . ?
C18 C17 H17A 119.4 . . ?
C16 C17 H17A 119.4 . . ?
C17 C18 C19 121.0(4) . . ?
C17 C18 C23 119.6(4) . . ?
C19 C18 C23 119.3(4) . . ?
C20 C19 C18 121.2(4) . . ?
C20 C19 H19A 119.4 . . ?
C18 C19 H19A 119.4 . . ?
C19 C20 C21 119.7(4) . . ?
C19 C20 H20A 120.1 . . ?
C21 C20 H20A 120.1 . . ?
C22 C21 C20 120.7(4) . . ?
C22 C21 H21A 119.6 . . ?
C20 C21 H21A 119.6 . . ?
C21 C22 C23 122.0(4) . . ?
C21 C22 H22A 119.0 . . ?
C23 C22 H22A 119.0 . . ?
C10 C23 C22 122.7(4) . . ?
C10 C23 C18 120.4(4) . . ?
C22 C23 C18 117.0(4) . . ?

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
C6 C1 C2 C3 -0.8(6) . . . . ?
C1 C2 C3 C4 0.4(7) . . . . ?
C2 C3 C4 C5 0.4(7) . . . . ?
C3 C4 C5 C6 -0.8(6) . . . . ?
C4 C5 C6 C1 0.4(6) . . . . ?
C4 C5 C6 C7 -177.7(3) . . . . ?
C2 C1 C6 C5 0.3(5) . . . . ?
C2 C1 C6 C7 178.6(3) . . . . ?
C5 C6 C7 O 162.2(4) . . . . ?
C1 C6 C7 O -16.0(5) . . . . ?
C5 C6 C7 C8 -18.0(5) . . . . ?
C1 C6 C7 C8 163.8(3) . . . . ?
O C7 C8 C9 -13.1(6) . . . . ?
C6 C7 C8 C9 167.1(4) . . . . ?
C7 C8 C9 C10 179.4(3) . . . . ?
C8 C9 C10 C23 -80.7(5) . . . . ?
C8 C9 C10 C11 97.7(5) . . . . ?
C23 C10 C11 C12 -175.7(3) . . . . ?
C9 C10 C11 C12 5.9(5) . . . . ?
C23 C10 C11 C16 4.0(5) . . . . ?
C9 C10 C11 C16 -174.4(3) . . . . ?
C10 C11 C12 C13 -179.7(4) . . . . ?
C16 C11 C12 C13 0.6(5) . . . . ?
C11 C12 C13 C14 1.2(6) . . . . ?
C12 C13 C14 C15 -1.7(7) . . . . ?
C13 C14 C15 C16 0.3(6) . . . . ?
C14 C15 C16 C17 -178.0(4) . . . . ?
C14 C15 C16 C11 1.5(5) . . . . ?
C10 C11 C16 C17 -2.1(5) . . . . ?
C12 C11 C16 C17 177.6(3) . . . . ?
C10 C11 C16 C15 178.4(3) . . . . ?
C12 C11 C16 C15 -1.9(5) . . . . ?
C15 C16 C17 C18 178.9(3) . . . . ?
C11 C16 C17 C18 -0.6(5) . . . . ?
C16 C17 C18 C19 -180.0(3) . . . . ?
C16 C17 C18 C23 1.4(5) . . . . ?
C17 C18 C19 C20 179.3(4) . . . . ?
C23 C18 C19 C20 -2.0(5) . . . . ?
C18 C19 C20 C21 0.2(6) . . . . ?
C19 C20 C21 C22 1.0(6) . . . . ?
C20 C21 C22 C23 -0.4(6) . . . . ?
C11 C10 C23 C22 176.1(3) . . . . ?
C9 C10 C23 C22 -5.5(5) . . . . ?
C11 C10 C23 C18 -3.3(5) . . . . ?
C9 C10 C23 C18 175.1(3) . . . . ?
C21 C22 C23 C10 179.2(4) . . . . ?
C21 C22 C23 C18 -1.4(5) . . . . ?
C17 C18 C23 C10 0.6(5) . . . . ?
C19 C18 C23 C10 -178.1(3) . . . . ?
C17 C18 C23 C22 -178.8(3) . . . . ?
C19 C18 C23 C22 2.5(5) . . . . ?

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.039

