# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_20110111
_database_code_depnum_ccdc_archive 'CCDC 1473633'
_audit_update_record             
;
2016-04-13 deposited with the CCDC.
2016-06-16 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24 H16 O'
_chemical_formula_moiety         'C24 H16 O'
_chemical_formula_weight         320.39
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y-1/2, -z-1/2'
'x-1/2, y, -z-1/2'
#------------------------------------------------------------------------------
_cell_length_a                   14.6652(4)
_cell_length_b                   8.6882(3)
_cell_length_c                   26.0272(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     3316.22(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    16014
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      68.23
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.016
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344.00
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.790
_exptl_absorpt_correction_T_max  0.990

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            34753
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_theta_max         68.230
_diffrn_reflns_theta_min         3.396
_diffrn_reflns_theta_full        68.230
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3039
_reflns_number_gt                1478
_reflns_threshold_expression     F>2.0σ(F)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1105
_refine_ls_R_factor_gt           0.0723
_refine_ls_wR_factor_ref         0.2471
_refine_ls_wR_factor_gt          0.1949
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3039
_refine_ls_number_parameters     258
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1431P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0038(6)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.93073(15) 0.4009(3) 0.16722(8) 0.0967(8) Uani 1 1 d . . .
C1 C 1.0282(2) 0.1982(4) 0.09443(12) 0.0804(9) Uani 1 1 d . . .
H1 H 0.968(2) 0.2300(12) 0.0853(4) 0.096 Uiso 1 1 calc R . .
C2 C 1.0604(2) 0.2495(4) 0.13871(12) 0.0783(9) Uani 1 1 d . . .
C3 C 1.0097(2) 0.3571(4) 0.17347(11) 0.0788(9) Uani 1 1 d . . .
C4 C 1.0722(2) 0.4009(4) 0.21499(10) 0.0754(9) Uani 1 1 d . . .
C5 C 1.1560(2) 0.3275(4) 0.20772(12) 0.0794(9) Uani 1 1 d . . .
C6 C 1.1544(2) 0.2233(4) 0.16135(12) 0.0868(10) Uani 1 1 d . . .
H6A H 1.1632(3) 0.109(3) 0.1720(3) 0.104 Uiso 1 1 calc R . .
H6B H 1.2053(12) 0.2535(7) 0.1353(6) 0.104 Uiso 1 1 calc R . .
C7 C 1.0585(3) 0.5020(4) 0.25560(12) 0.0863(11) Uani 1 1 d . . .
H7 H 0.999(2) 0.552(2) 0.2607(2) 0.104 Uiso 1 1 calc R . .
C8 C 1.1300(3) 0.5305(5) 0.28851(13) 0.0938(11) Uani 1 1 d . . .
H8 H 1.1216(4) 0.605(3) 0.3182(11) 0.113 Uiso 1 1 calc R . .
C9 C 1.2140(3) 0.4582(5) 0.28149(12) 0.0944(11) Uani 1 1 d . . .
H9 H 1.268(2) 0.4812(9) 0.3073(10) 0.113 Uiso 1 1 calc R . .
C10 C 1.2276(3) 0.3569(5) 0.24127(12) 0.0902(10) Uani 1 1 d . . .
H10 H 1.290(2) 0.3036(19) 0.2362(2) 0.108 Uiso 1 1 calc R . .
C11 C 1.0759(2) 0.0968(4) 0.05762(11) 0.0749(9) Uani 1 1 d . . .
C12 C 1.09674(18) 0.1512(4) 0.00812(12) 0.0772(9) Uani 1 1 d . . .
C13 C 1.0774(2) 0.3049(5) -0.00817(13) 0.0858(10) Uani 1 1 d . . .
H13 H 1.0469(11) 0.379(3) 0.0170(9) 0.103 Uiso 1 1 calc R . .
C14 C 1.0984(2) 0.3544(6) -0.05620(14) 0.0941(11) Uani 1 1 d . . .
H14 H 1.0821(7) 0.465(4) -0.0672(4) 0.113 Uiso 1 1 calc R . .
C15 C 1.1426(3) 0.2547(6) -0.09143(15) 0.1024(13) Uani 1 1 d . . .
H15 H 1.1590(7) 0.2946(17) -0.1292(14) 0.123 Uiso 1 1 calc R . .
C16 C 1.1644(3) 0.1078(6) -0.07725(13) 0.0959(12) Uani 1 1 d . . .
H16 H 1.1973(13) 0.035(3) -0.1034(10) 0.115 Uiso 1 1 calc R . .
C17 C 1.1429(2) 0.0522(4) -0.02744(11) 0.0800(9) Uani 1 1 d . . .
C18 C 1.1647(2) -0.0981(5) -0.01255(13) 0.0861(10) Uani 1 1 d . . .
H18 H 1.1967(12) -0.167(3) -0.0379(9) 0.103 Uiso 1 1 calc R . .
C19 C 1.14381(19) -0.1547(4) 0.03575(13) 0.0793(9) Uani 1 1 d . . .
C20 C 1.1639(2) -0.3105(5) 0.05042(17) 0.0909(11) Uani 1 1 d . . .
H20 H 1.1951(12) -0.378(2) 0.0260(9) 0.109 Uiso 1 1 calc R . .
C21 C 1.1409(2) -0.3660(5) 0.09698(17) 0.0978(11) Uani 1 1 d . . .
H21 H 1.1579(7) -0.484(5) 0.1072(4) 0.117 Uiso 1 1 calc R . .
C22 C 1.0948(2) -0.2711(5) 0.13257(16) 0.0947(11) Uani 1 1 d . . .
H22 H 1.0757(7) -0.3169(16) 0.1699(12) 0.114 Uiso 1 1 calc R . .
C23 C 1.0741(2) -0.1215(5) 0.12040(13) 0.0855(10) Uani 1 1 d . . .
H23 H 1.0422(12) -0.057(2) 0.1458(9) 0.103 Uiso 1 1 calc R . .
C24 C 1.0977(2) -0.0568(4) 0.07189(12) 0.0757(9) Uani 1 1 d . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1.1 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.1.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C3 1.230(3) . ?
C1 C2 1.323(4) . ?
C1 C11 1.477(4) . ?
C1 H1 0.9561 . ?
C2 C3 1.498(4) . ?
C2 C6 1.517(4) . ?
C3 C4 1.467(4) . ?
C4 C7 1.389(4) . ?
C4 C5 1.397(4) . ?
C5 C10 1.390(4) . ?
C5 C6 1.509(4) . ?
C6 H6A 1.0424 . ?
C6 H6B 1.0424 . ?
C7 C8 1.377(5) . ?
C7 H7 0.9765 . ?
C8 C9 1.394(5) . ?
C8 H8 1.0170 . ?
C9 C10 1.382(5) . ?
C9 H9 1.0584 . ?
C10 H10 1.0376 . ?
C11 C12 1.406(4) . ?
C11 C24 1.422(4) . ?
C12 C13 1.430(5) . ?
C12 C17 1.434(4) . ?
C13 C14 1.357(4) . ?
C13 H13 1.0228 . ?
C14 C15 1.418(6) . ?
C14 H14 1.0321 . ?
C15 C16 1.366(6) . ?
C15 H15 1.0689 . ?
C16 C17 1.419(5) . ?
C16 H16 1.0449 . ?
C17 C18 1.398(5) . ?
C18 C19 1.384(5) . ?
C18 H18 1.0092 . ?
C19 C20 1.437(5) . ?
C19 C24 1.438(4) . ?
C20 C21 1.347(5) . ?
C20 H20 0.9777 . ?
C21 C22 1.412(5) . ?
C21 H21 1.0887 . ?
C22 C23 1.372(5) . ?
C22 H22 1.0861 . ?
C23 C24 1.424(4) . ?
C23 H23 0.9847 . ?

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 C11 126.7(3) . . ?
C2 C1 H1 116.7 . . ?
C11 C1 H1 116.7 . . ?
C1 C2 C3 124.0(3) . . ?
C1 C2 C6 127.7(3) . . ?
C3 C2 C6 108.1(3) . . ?
O1 C3 C4 127.3(3) . . ?
O1 C3 C2 125.5(3) . . ?
C4 C3 C2 107.3(3) . . ?
C7 C4 C5 121.3(3) . . ?
C7 C4 C3 129.4(3) . . ?
C5 C4 C3 109.3(3) . . ?
C10 C5 C4 119.7(3) . . ?
C10 C5 C6 128.6(3) . . ?
C4 C5 C6 111.7(3) . . ?
C5 C6 C2 103.5(3) . . ?
C5 C6 H6A 111.1 . . ?
C2 C6 H6A 111.1 . . ?
C5 C6 H6B 111.1 . . ?
C2 C6 H6B 111.1 . . ?
H6A C6 H6B 109.0 . . ?
C8 C7 C4 118.5(3) . . ?
C8 C7 H7 120.8 . . ?
C4 C7 H7 120.8 . . ?
C7 C8 C9 120.7(4) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 120.9(4) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C5 118.9(4) . . ?
C9 C10 H10 120.5 . . ?
C5 C10 H10 120.5 . . ?
C12 C11 C24 120.4(3) . . ?
C12 C11 C1 119.8(3) . . ?
C24 C11 C1 119.8(3) . . ?
C11 C12 C13 122.9(3) . . ?
C11 C12 C17 119.5(3) . . ?
C13 C12 C17 117.6(3) . . ?
C14 C13 C12 121.6(4) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 120.4(4) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 120.2(4) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.9(4) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 121.3(3) . . ?
C18 C17 C12 119.3(3) . . ?
C16 C17 C12 119.4(4) . . ?
C19 C18 C17 122.2(3) . . ?
C19 C18 H18 118.9 . . ?
C17 C18 H18 118.9 . . ?
C18 C19 C20 122.1(3) . . ?
C18 C19 C24 119.2(4) . . ?
C20 C19 C24 118.7(3) . . ?
C21 C20 C19 121.7(4) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C22 120.1(4) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 120.5(4) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 121.6(4) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C11 C24 C23 123.2(3) . . ?
C11 C24 C19 119.4(3) . . ?
C23 C24 C19 117.4(3) . . ?

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
C11 C1 C2 C3 177.6(3) . . . . ?
C11 C1 C2 C6 2.9(6) . . . . ?
C1 C2 C3 O1 5.8(6) . . . . ?
C6 C2 C3 O1 -178.6(3) . . . . ?
C1 C2 C3 C4 -173.2(3) . . . . ?
C6 C2 C3 C4 2.4(4) . . . . ?
O1 C3 C4 C7 -1.5(6) . . . . ?
C2 C3 C4 C7 177.6(3) . . . . ?
O1 C3 C4 C5 -179.2(3) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C7 C4 C5 C10 -0.7(5) . . . . ?
C3 C4 C5 C10 177.2(3) . . . . ?
C7 C4 C5 C6 179.9(3) . . . . ?
C3 C4 C5 C6 -2.2(4) . . . . ?
C10 C5 C6 C2 -175.8(3) . . . . ?
C4 C5 C6 C2 3.6(4) . . . . ?
C1 C2 C6 C5 171.9(3) . . . . ?
C3 C2 C6 C5 -3.5(3) . . . . ?
C5 C4 C7 C8 0.9(5) . . . . ?
C3 C4 C7 C8 -176.6(3) . . . . ?
C4 C7 C8 C9 -0.7(5) . . . . ?
C7 C8 C9 C10 0.3(6) . . . . ?
C8 C9 C10 C5 -0.1(6) . . . . ?
C4 C5 C10 C9 0.3(5) . . . . ?
C6 C5 C10 C9 179.6(3) . . . . ?
C2 C1 C11 C12 -116.5(4) . . . . ?
C2 C1 C11 C24 65.6(5) . . . . ?
C24 C11 C12 C13 -179.3(3) . . . . ?
C1 C11 C12 C13 2.8(4) . . . . ?
C24 C11 C12 C17 -2.0(4) . . . . ?
C1 C11 C12 C17 -179.9(3) . . . . ?
C11 C12 C13 C14 179.9(3) . . . . ?
C17 C12 C13 C14 2.6(5) . . . . ?
C12 C13 C14 C15 -1.6(5) . . . . ?
C13 C14 C15 C16 0.0(5) . . . . ?
C14 C15 C16 C17 0.3(5) . . . . ?
C15 C16 C17 C18 179.8(3) . . . . ?
C15 C16 C17 C12 0.8(5) . . . . ?
C11 C12 C17 C18 1.3(4) . . . . ?
C13 C12 C17 C18 178.7(3) . . . . ?
C11 C12 C17 C16 -179.6(3) . . . . ?
C13 C12 C17 C16 -2.2(4) . . . . ?
C16 C17 C18 C19 -179.6(3) . . . . ?
C12 C17 C18 C19 -0.5(5) . . . . ?
C17 C18 C19 C20 178.2(3) . . . . ?
C17 C18 C19 C24 0.4(5) . . . . ?
C18 C19 C20 C21 -178.0(3) . . . . ?
C24 C19 C20 C21 -0.2(5) . . . . ?
C19 C20 C21 C22 0.8(5) . . . . ?
C20 C21 C22 C23 -0.8(5) . . . . ?
C21 C22 C23 C24 0.2(5) . . . . ?
C12 C11 C24 C23 -176.6(3) . . . . ?
C1 C11 C24 C23 1.3(4) . . . . ?
C12 C11 C24 C19 1.9(4) . . . . ?
C1 C11 C24 C19 179.8(3) . . . . ?
C22 C23 C24 C11 178.9(3) . . . . ?
C22 C23 C24 C19 0.3(5) . . . . ?
C18 C19 C24 C11 -1.1(4) . . . . ?
C20 C19 C24 C11 -179.0(3) . . . . ?
C18 C19 C24 C23 177.5(3) . . . . ?
C20 C19 C24 C23 -0.3(4) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_20110114
_database_code_depnum_ccdc_archive 'CCDC 1473634'
_audit_update_record             
;
2016-04-13 deposited with the CCDC.
2016-06-16 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24 H16 O'
_chemical_formula_moiety         'C24 H16 O'
_chemical_formula_weight         320.39
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 -1/2-X,-1/2+Y,+Z
7 +X,-1/2-Y,-1/2+Z
8 -1/2+X,+Y,-1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   14.6606(18)
_cell_length_b                   8.6890(12)
_cell_length_c                   25.950(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     3305.7(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2859
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      67.61
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.016
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344.00
_exptl_absorpt_coefficient_mu    0.599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.667
_exptl_absorpt_correction_T_max  0.990

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            34861
_diffrn_reflns_av_R_equivalents  0.1011
_diffrn_reflns_theta_max         68.252
_diffrn_reflns_theta_min         3.406
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_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             3036
_reflns_number_gt                1245
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1301
_refine_ls_R_factor_gt           0.0648
_refine_ls_wR_factor_ref         0.2170
_refine_ls_wR_factor_gt          0.1692
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3036
_refine_ls_number_parameters     262
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1058P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.008
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.56969(17) -0.4010(3) 0.83240(9) 0.1073(9) Uani 1 1 d . . . . .
C1 C 0.4722(3) -0.1993(4) 0.90538(17) 0.0890(11) Uani 1 1 d . . . . .
H1 H 0.529(2) -0.235(3) 0.9149(11) 0.080(10) Uiso 1 1 d . . . . .
C2 C 0.4399(2) -0.2516(4) 0.86102(15) 0.0855(10) Uani 1 1 d . . . . .
C4 C 0.4276(2) -0.4023(4) 0.78568(14) 0.0830(10) Uani 1 1 d . . . . .
C5 C 0.3444(2) -0.3290(4) 0.79236(14) 0.0859(10) Uani 1 1 d . . . . .
C6 C 0.3462(2) -0.2251(4) 0.83905(14) 0.0973(11) Uani 1 1 d . . . . .
H6A H 0.3378 -0.1183 0.8293 0.117 Uiso 1 1 calc R U . . .
H6B H 0.2992 -0.2537 0.8636 0.117 Uiso 1 1 calc R U . . .
C7 C 0.4406(3) -0.5035(4) 0.74489(15) 0.0931(11) Uani 1 1 d . . . . .
H7 H 0.4967 -0.5513 0.7399 0.112 Uiso 1 1 calc R U . . .
C8 C 0.3688(3) -0.5316(5) 0.71188(15) 0.1035(12) Uani 1 1 d . . . . .
H8 H 0.3763 -0.5993 0.6844 0.124 Uiso 1 1 calc R U . . .
C9 C 0.2856(3) -0.4598(5) 0.71928(15) 0.1046(12) Uani 1 1 d . . . . .
H9 H 0.2377 -0.4800 0.6968 0.126 Uiso 1 1 calc R U . . .
C10 C 0.2727(3) -0.3593(4) 0.75928(16) 0.0996(11) Uani 1 1 d . . . . .
H10 H 0.2165 -0.3121 0.7641 0.120 Uiso 1 1 calc R U . . .
C11 C 0.4249(2) -0.0967(4) 0.94233(14) 0.0861(10) Uani 1 1 d . . . . .
C12 C 0.4037(2) 0.0554(4) 0.92821(15) 0.0851(10) Uani 1 1 d . . . . .
C13 C 0.4270(3) 0.1196(5) 0.87963(17) 0.0934(11) Uani 1 1 d . . . . .
H13 H 0.461(2) 0.046(4) 0.8557(14) 0.113(13) Uiso 1 1 d . . . . .
C14 C 0.4063(3) 0.2664(6) 0.8674(2) 0.1035(12) Uani 1 1 d . . . . .
H14 H 0.424(3) 0.310(5) 0.8332(16) 0.132(16) Uiso 1 1 d . . . . .
C15 C 0.3599(3) 0.3616(5) 0.9029(2) 0.1097(13) Uani 1 1 d . . . . .
H15 H 0.3454 0.4622 0.8939 0.132 Uiso 1 1 calc R U . . .
C16 C 0.3366(3) 0.3079(5) 0.9496(2) 0.0999(13) Uani 1 1 d . . . . .
H16 H 0.306(2) 0.366(4) 0.9756(13) 0.098(12) Uiso 1 1 d . . . . .
C17 C 0.3574(2) 0.1536(5) 0.96426(17) 0.0901(11) Uani 1 1 d . . . . .
C18 C 0.3356(2) 0.0976(6) 1.01306(18) 0.0962(11) Uani 1 1 d . . . . .
H18 H 0.305(2) 0.176(4) 1.0398(13) 0.105(11) Uiso 1 1 d . . . . .
C19 C 0.3574(2) -0.0527(5) 1.02757(15) 0.0906(11) Uani 1 1 d . . . . .
C20 C 0.3353(3) -0.1101(8) 1.07769(18) 0.1071(13) Uani 1 1 d . . . . .
H20 H 0.300(2) -0.035(4) 1.1009(14) 0.112(13) Uiso 1 1 d . . . . .
C21 C 0.3567(3) -0.2557(7) 1.0910(2) 0.1119(14) Uani 1 1 d . . . . .
H21 H 0.338(3) -0.294(6) 1.126(2) 0.17(2) Uiso 1 1 d . . . . .
C22 C 0.4010(3) -0.3557(7) 1.0562(2) 0.1088(13) Uani 1 1 d . . . . .
H22 H 0.413(2) -0.473(5) 1.0639(15) 0.122(14) Uiso 1 1 d . . . . .
C23 C 0.4227(3) -0.3052(6) 1.00762(19) 0.0956(11) Uani 1 1 d . . . . .
H23 H 0.450(2) -0.376(4) 0.9823(13) 0.092(11) Uiso 1 1 d . . . . .
C24 C 0.4032(2) -0.1525(5) 0.99232(15) 0.0849(10) Uani 1 1 d . . . . .
C3 C 0.4905(3) -0.3587(4) 0.82695(13) 0.0858(10) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1.1 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.1.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C3 1.226(4) . ?
C1 C2 1.325(5) . ?
C1 C11 1.482(5) . ?
C1 H1 0.92(3) . ?
C2 C3 1.482(5) . ?
C2 C6 1.505(5) . ?
C4 C5 1.387(4) . ?
C4 C7 1.389(5) . ?
C4 C3 1.463(4) . ?
C5 C10 1.382(5) . ?
C5 C6 1.511(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.380(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.383(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.369(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.406(5) . ?
C11 C24 1.420(5) . ?
C12 C13 1.420(5) . ?
C12 C17 1.437(5) . ?
C13 C14 1.349(5) . ?
C13 H13 1.02(4) . ?
C14 C15 1.413(6) . ?
C14 H14 1.00(4) . ?
C15 C16 1.342(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.427(5) . ?
C16 H16 0.95(3) . ?
C17 C18 1.393(5) . ?
C18 C19 1.396(5) . ?
C18 H18 1.07(4) . ?
C19 C24 1.428(5) . ?
C19 C20 1.430(5) . ?
C20 C21 1.348(6) . ?
C20 H20 1.03(4) . ?
C21 C22 1.411(6) . ?
C21 H21 1.01(5) . ?
C22 C23 1.373(6) . ?
C22 H22 1.05(4) . ?
C23 C24 1.414(5) . ?
C23 H23 0.98(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C11 126.9(4) . . ?
C2 C1 H1 116.3(19) . . ?
C11 C1 H1 116.7(19) . . ?
C1 C2 C3 123.7(4) . . ?
C1 C2 C6 127.1(3) . . ?
C3 C2 C6 109.1(3) . . ?
C5 C4 C7 120.5(4) . . ?
C5 C4 C3 110.1(3) . . ?
C7 C4 C3 129.4(3) . . ?
C10 C5 C4 120.2(4) . . ?
C10 C5 C6 128.7(3) . . ?
C4 C5 C6 111.1(3) . . ?
C2 C6 C5 103.2(3) . . ?
C2 C6 H6A 111.1 . . ?
C5 C6 H6A 111.1 . . ?
C2 C6 H6B 111.1 . . ?
C5 C6 H6B 111.1 . . ?
H6A C6 H6B 109.1 . . ?
C8 C7 C4 118.7(4) . . ?
C8 C7 H7 120.7 . . ?
C4 C7 H7 120.7 . . ?
C7 C8 C9 120.5(4) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 121.0(4) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C5 119.2(4) . . ?
C9 C10 H10 120.4 . . ?
C5 C10 H10 120.4 . . ?
C12 C11 C24 120.6(3) . . ?
C12 C11 C1 120.0(4) . . ?
C24 C11 C1 119.4(4) . . ?
C11 C12 C13 123.2(4) . . ?
C11 C12 C17 119.5(4) . . ?
C13 C12 C17 117.3(4) . . ?
C14 C13 C12 121.7(5) . . ?
C14 C13 H13 124(2) . . ?
C12 C13 H13 114(2) . . ?
C13 C14 C15 120.6(5) . . ?
C13 C14 H14 120(2) . . ?
C15 C14 H14 119(2) . . ?
C16 C15 C14 120.5(5) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.8(5) . . ?
C15 C16 H16 125(2) . . ?
C17 C16 H16 114(2) . . ?
C18 C17 C16 121.4(4) . . ?
C18 C17 C12 119.5(4) . . ?
C16 C17 C12 119.1(4) . . ?
C17 C18 C19 121.3(4) . . ?
C17 C18 H18 117.6(18) . . ?
C19 C18 H18 121.0(18) . . ?
C18 C19 C24 120.2(4) . . ?
C18 C19 C20 121.3(4) . . ?
C24 C19 C20 118.5(4) . . ?
C21 C20 C19 120.5(5) . . ?
C21 C20 H20 124(2) . . ?
C19 C20 H20 115(2) . . ?
C20 C21 C22 121.3(5) . . ?
C20 C21 H21 119(3) . . ?
C22 C21 H21 120(3) . . ?
C23 C22 C21 119.9(5) . . ?
C23 C22 H22 116(2) . . ?
C21 C22 H22 124(2) . . ?
C22 C23 C24 120.7(5) . . ?
C22 C23 H23 120.4(19) . . ?
C24 C23 H23 118.8(19) . . ?
C23 C24 C11 122.1(4) . . ?
C23 C24 C19 119.0(4) . . ?
C11 C24 C19 118.9(4) . . ?
O1 C3 C4 127.1(3) . . ?
O1 C3 C2 126.4(3) . . ?
C4 C3 C2 106.5(3) . . ?

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
C11 C1 C2 C3 -177.7(3) . . . . ?
C11 C1 C2 C6 -3.1(6) . . . . ?
C7 C4 C5 C10 1.8(5) . . . . ?
C3 C4 C5 C10 -176.7(3) . . . . ?
C7 C4 C5 C6 180.0(3) . . . . ?
C3 C4 C5 C6 1.5(4) . . . . ?
C1 C2 C6 C5 -172.4(4) . . . . ?
C3 C2 C6 C5 2.9(4) . . . . ?
C10 C5 C6 C2 175.3(4) . . . . ?
C4 C5 C6 C2 -2.7(4) . . . . ?
C5 C4 C7 C8 -1.2(5) . . . . ?
C3 C4 C7 C8 177.0(3) . . . . ?
C4 C7 C8 C9 0.2(6) . . . . ?
C7 C8 C9 C10 0.1(6) . . . . ?
C8 C9 C10 C5 0.4(6) . . . . ?
C4 C5 C10 C9 -1.4(6) . . . . ?
C6 C5 C10 C9 -179.2(4) . . . . ?
C2 C1 C11 C12 -65.8(5) . . . . ?
C2 C1 C11 C24 115.7(4) . . . . ?
C24 C11 C12 C13 177.3(3) . . . . ?
C1 C11 C12 C13 -1.2(5) . . . . ?
C24 C11 C12 C17 -1.8(5) . . . . ?
C1 C11 C12 C17 179.7(3) . . . . ?
C11 C12 C13 C14 -179.5(3) . . . . ?
C17 C12 C13 C14 -0.4(5) . . . . ?
C12 C13 C14 C15 -0.2(6) . . . . ?
C13 C14 C15 C16 0.7(6) . . . . ?
C14 C15 C16 C17 -0.6(6) . . . . ?
C15 C16 C17 C18 178.4(3) . . . . ?
C15 C16 C17 C12 -0.1(5) . . . . ?
C11 C12 C17 C18 1.2(5) . . . . ?
C13 C12 C17 C18 -177.9(3) . . . . ?
C11 C12 C17 C16 179.6(3) . . . . ?
C13 C12 C17 C16 0.5(5) . . . . ?
C16 C17 C18 C19 -178.9(3) . . . . ?
C12 C17 C18 C19 -0.5(5) . . . . ?
C17 C18 C19 C24 0.3(5) . . . . ?
C17 C18 C19 C20 179.9(3) . . . . ?
C18 C19 C20 C21 179.9(4) . . . . ?
C24 C19 C20 C21 -0.5(5) . . . . ?
C19 C20 C21 C22 -0.2(6) . . . . ?
C20 C21 C22 C23 -0.3(6) . . . . ?
C21 C22 C23 C24 1.6(6) . . . . ?
C22 C23 C24 C11 180.0(3) . . . . ?
C22 C23 C24 C19 -2.3(5) . . . . ?
C12 C11 C24 C23 179.4(3) . . . . ?
C1 C11 C24 C23 -2.1(5) . . . . ?
C12 C11 C24 C19 1.6(5) . . . . ?
C1 C11 C24 C19 -179.9(3) . . . . ?
C18 C19 C24 C23 -178.7(3) . . . . ?
C20 C19 C24 C23 1.7(5) . . . . ?
C18 C19 C24 C11 -0.8(5) . . . . ?
C20 C19 C24 C11 179.5(3) . . . . ?
C5 C4 C3 O1 -179.1(3) . . . . ?
C7 C4 C3 O1 2.5(6) . . . . ?
C5 C4 C3 C2 0.4(4) . . . . ?
C7 C4 C3 C2 -177.9(3) . . . . ?
C1 C2 C3 O1 -7.1(6) . . . . ?
C6 C2 C3 O1 177.4(3) . . . . ?
C1 C2 C3 C4 173.3(3) . . . . ?
C6 C2 C3 C4 -2.1(4) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one
# structure analysis in the CIF.

_shelxl_version_number           2013-4


####################################################################### 
# 
# 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_anth_before_uv
_database_code_depnum_ccdc_archive 'CCDC 1482558'
_audit_update_record             
;
2016-05-30 deposited with the CCDC.
2016-06-16 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24 H16 O'
_chemical_formula_moiety         'C24 H16 O'
_chemical_formula_weight         320.39
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 -1/2-X,-1/2+Y,+Z
7 +X,-1/2-Y,-1/2+Z
8 -1/2+X,+Y,-1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   14.6697(12)
_cell_length_b                   8.6824(8)
_cell_length_c                   25.993(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     3310.6(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8663
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      27.47
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344.00
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.393
_exptl_absorpt_correction_T_max  0.992

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            26949
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         3.135
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3630
_reflns_number_gt                2372
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1183
_refine_ls_R_factor_gt           0.0721
_refine_ls_wR_factor_ref         0.1460
_refine_ls_wR_factor_gt          0.1273
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         3630
_refine_ls_number_parameters     290
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0433P)²+1.4268P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.14
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 -0.06910(11) -0.4007(2) 0.66725(7) 0.0681(5) Uani 1 1 d . . . . .
C1 C 0.09754(15) 0.0567(3) 0.57188(9) 0.0500(6) Uani 1 1 d . . . . .
C2 C 0.07364(18) 0.1209(3) 0.62030(10) 0.0592(7) Uani 1 1 d . . . . .
C3 C 0.09463(19) 0.2692(3) 0.63254(12) 0.0691(8) Uani 1 1 d . . . . .
C4 C 0.14051(19) 0.3644(4) 0.59706(13) 0.0716(8) Uani 1 1 d . . . . .
C5 C 0.16353(18) 0.3105(3) 0.55082(13) 0.0641(7) Uani 1 1 d . . . . .
C6 C 0.14328(14) 0.1540(3) 0.53585(10) 0.0536(6) Uani 1 1 d . . . . .
C7 C 0.16457(16) 0.0981(3) 0.48767(10) 0.0589(7) Uani 1 1 d . . . . .
C8 C 0.14280(15) -0.0517(3) 0.47260(9) 0.0550(6) Uani 1 1 d . . . . .
C9 C 0.16445(19) -0.1099(4) 0.42286(10) 0.0698(8) Uani 1 1 d . . . . .
C10 C 0.1421(2) -0.2542(4) 0.40882(11) 0.0755(9) Uani 1 1 d . . . . .
C11 C 0.0984(2) -0.3540(4) 0.44397(11) 0.0702(8) Uani 1 1 d . . . . .
C12 C 0.07760(18) -0.3048(3) 0.49200(11) 0.0599(7) Uani 1 1 d . . . . .
C13 C 0.09724(14) -0.1514(3) 0.50833(9) 0.0501(6) Uani 1 1 d . . . . .
C14 C 0.07599(15) -0.0964(3) 0.55778(8) 0.0485(6) Uani 1 1 d . . . . .
C15 C 0.02804(17) -0.1991(3) 0.59452(9) 0.0508(6) Uani 1 1 d . . . . .
C16 C 0.06069(15) -0.2491(3) 0.63892(9) 0.0501(6) Uani 1 1 d . . . . .
C17 C 0.00947(16) -0.3573(3) 0.67332(8) 0.0506(6) Uani 1 1 d . . . . .
C18 C 0.07239(16) -0.4008(3) 0.71484(8) 0.0481(6) Uani 1 1 d . . . . .
C19 C 0.0593(2) -0.5024(3) 0.75566(9) 0.0579(7) Uani 1 1 d . . . . .
C20 C 0.1305(2) -0.5303(3) 0.78857(10) 0.0667(8) Uani 1 1 d . . . . .
C21 C 0.2141(2) -0.4585(3) 0.78140(10) 0.0673(7) Uani 1 1 d . . . . .
C22 C 0.2275(2) -0.3572(3) 0.74108(10) 0.0612(7) Uani 1 1 d . . . . .
C23 C 0.15586(16) -0.3277(3) 0.70774(9) 0.0516(6) Uani 1 1 d . . . . .
C24 C 0.15425(18) -0.2237(4) 0.66125(11) 0.0601(7) Uani 1 1 d . . . . .
H2 H 0.0407(16) 0.058(3) 0.6457(10) 0.068(8) Uiso 1 1 d . . . . .
H3 H 0.0757(19) 0.311(3) 0.6682(12) 0.097(10) Uiso 1 1 d . . . . .
H4 H 0.1535(18) 0.476(4) 0.6071(10) 0.090(9) Uiso 1 1 d . . . . .
H5 H 0.1919(17) 0.364(3) 0.5240(10) 0.074(8) Uiso 1 1 d . . . . .
H7 H 0.1949(16) 0.166(3) 0.4631(9) 0.068(7) Uiso 1 1 d . . . . .
H9 H 0.1956(19) -0.039(3) 0.3984(11) 0.090(9) Uiso 1 1 d . . . . .
H10 H 0.1559(18) -0.294(3) 0.3739(11) 0.083(9) Uiso 1 1 d . . . . .
H11 H 0.0851(18) -0.459(3) 0.4341(10) 0.079(9) Uiso 1 1 d . . . . .
H12 H 0.0490(14) -0.374(3) 0.5165(9) 0.055(7) Uiso 1 1 d . . . . .
H15 H -0.0335(17) -0.235(3) 0.5846(9) 0.065(7) Uiso 1 1 d . . . . .
H19 H 0.0015(18) -0.550(3) 0.7585(8) 0.057(7) Uiso 1 1 d . . . . .
H20 H 0.1238(17) -0.600(3) 0.8180(10) 0.078(8) Uiso 1 1 d . . . . .
H21 H 0.2656(19) -0.481(3) 0.8058(11) 0.084(9) Uiso 1 1 d . . . . .
H22 H 0.2873(19) -0.308(3) 0.7349(10) 0.083(9) Uiso 1 1 d . . . . .
H24A H 0.2036(18) -0.251(3) 0.6358(10) 0.079(8) Uiso 1 1 d . . . . .
H24B H 0.1625(18) -0.118(4) 0.6719(10) 0.084(9) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL Version 2014/6 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.223(3) . ?
C1 C14 1.414(3) . ?
C1 C2 1.420(3) . ?
C1 C6 1.428(3) . ?
C2 C3 1.362(4) . ?
C2 H2 0.98(2) . ?
C3 C4 1.409(4) . ?
C3 H3 1.03(3) . ?
C4 C5 1.333(4) . ?
C4 H4 1.02(3) . ?
C5 C6 1.445(4) . ?
C5 H5 0.93(3) . ?
C6 C7 1.379(4) . ?
C7 C8 1.395(4) . ?
C7 H7 0.98(3) . ?
C8 C9 1.424(4) . ?
C8 C13 1.435(3) . ?
C9 C10 1.346(4) . ?
C9 H9 1.00(3) . ?
C10 C11 1.413(4) . ?
C10 H10 0.99(3) . ?
C11 C12 1.355(4) . ?
C11 H11 0.96(3) . ?
C12 C13 1.428(4) . ?
C12 H12 0.97(2) . ?
C13 C14 1.406(3) . ?
C14 C15 1.484(3) . ?
C15 C16 1.323(3) . ?
C15 H15 0.99(2) . ?
C16 C17 1.499(3) . ?
C16 C24 1.506(3) . ?
C17 C18 1.469(3) . ?
C18 C23 1.392(3) . ?
C18 C19 1.393(3) . ?
C19 C20 1.371(4) . ?
C19 H19 0.95(2) . ?
C20 C21 1.389(4) . ?
C20 H20 0.98(3) . ?
C21 C22 1.382(4) . ?
C21 H21 1.01(3) . ?
C22 C23 1.386(3) . ?
C22 H22 0.99(3) . ?
C23 C24 1.509(3) . ?
C24 H24A 1.01(3) . ?
C24 H24B 0.97(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 C1 C2 122.9(2) . . ?
C14 C1 C6 119.4(2) . . ?
C2 C1 C6 117.7(2) . . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 H2 118.7(14) . . ?
C1 C2 H2 119.8(14) . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 118.6(17) . . ?
C4 C3 H3 120.8(17) . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 121.0(16) . . ?
C3 C4 H4 118.6(16) . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5 127.7(17) . . ?
C6 C5 H5 110.9(17) . . ?
C7 C6 C1 119.6(2) . . ?
C7 C6 C5 121.9(2) . . ?
C1 C6 C5 118.4(2) . . ?
C6 C7 C8 122.1(2) . . ?
C6 C7 H7 119.1(15) . . ?
C8 C7 H7 118.8(15) . . ?
C7 C8 C9 122.3(3) . . ?
C7 C8 C13 119.2(2) . . ?
C9 C8 C13 118.5(3) . . ?
C10 C9 C8 121.5(3) . . ?
C10 C9 H9 121.0(17) . . ?
C8 C9 H9 117.5(17) . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 H10 121.6(16) . . ?
C11 C10 H10 118.0(16) . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.7(17) . . ?
C10 C11 H11 119.9(17) . . ?
C11 C12 C13 121.5(3) . . ?
C11 C12 H12 120.6(14) . . ?
C13 C12 H12 117.9(13) . . ?
C14 C13 C12 123.0(2) . . ?
C14 C13 C8 119.3(2) . . ?
C12 C13 C8 117.7(2) . . ?
C13 C14 C1 120.4(2) . . ?
C13 C14 C15 119.3(2) . . ?
C1 C14 C15 120.3(2) . . ?
C16 C15 C14 125.9(2) . . ?
C16 C15 H15 117.0(14) . . ?
C14 C15 H15 117.0(14) . . ?
C15 C16 C17 123.0(2) . . ?
C15 C16 C24 128.2(2) . . ?
C17 C16 C24 108.6(2) . . ?
O1 C17 C18 127.4(2) . . ?
O1 C17 C16 126.1(2) . . ?
C18 C17 C16 106.5(2) . . ?
C23 C18 C19 120.7(2) . . ?
C23 C18 C17 109.8(2) . . ?
C19 C18 C17 129.5(2) . . ?
C20 C19 C18 118.9(3) . . ?
C20 C19 H19 123.9(14) . . ?
C18 C19 H19 117.3(14) . . ?
C19 C20 C21 120.6(3) . . ?
C19 C20 H20 121.4(16) . . ?
C21 C20 H20 118.0(16) . . ?
C22 C21 C20 120.9(3) . . ?
C22 C21 H21 119.8(15) . . ?
C20 C21 H21 119.3(15) . . ?
C21 C22 C23 118.9(3) . . ?
C21 C22 H22 121.7(16) . . ?
C23 C22 H22 119.3(16) . . ?
C22 C23 C18 120.0(2) . . ?
C22 C23 C24 128.6(2) . . ?
C18 C23 C24 111.4(2) . . ?
C16 C24 C23 103.6(2) . . ?
C16 C24 H24A 111.5(15) . . ?
C23 C24 H24A 111.8(15) . . ?
C16 C24 H24B 111.3(16) . . ?
C23 C24 H24B 109.8(16) . . ?
H24A C24 H24B 109(2) . . ?

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 -179.4(2) . . . . ?
C6 C1 C2 C3 -1.0(4) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C14 C1 C6 C7 0.9(3) . . . . ?
C2 C1 C6 C7 -177.5(2) . . . . ?
C14 C1 C6 C5 179.2(2) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C4 C5 C6 C7 178.3(2) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C1 C6 C7 C8 0.0(3) . . . . ?
C5 C6 C7 C8 -178.2(2) . . . . ?
C6 C7 C8 C9 179.9(2) . . . . ?
C6 C7 C8 C13 -0.3(3) . . . . ?
C7 C8 C9 C10 -179.4(3) . . . . ?
C13 C8 C9 C10 0.8(4) . . . . ?
C8 C9 C10 C11 -1.7(4) . . . . ?
C9 C10 C11 C12 0.7(4) . . . . ?
C10 C11 C12 C13 1.2(4) . . . . ?
C11 C12 C13 C14 179.6(2) . . . . ?
C11 C12 C13 C8 -2.0(4) . . . . ?
C7 C8 C13 C14 -0.3(3) . . . . ?
C9 C8 C13 C14 179.5(2) . . . . ?
C7 C8 C13 C12 -178.8(2) . . . . ?
C9 C8 C13 C12 1.0(3) . . . . ?
C12 C13 C14 C1 179.7(2) . . . . ?
C8 C13 C14 C1 1.3(3) . . . . ?
C12 C13 C14 C15 -2.2(3) . . . . ?
C8 C13 C14 C15 179.4(2) . . . . ?
C2 C1 C14 C13 176.8(2) . . . . ?
C6 C1 C14 C13 -1.6(3) . . . . ?
C2 C1 C14 C15 -1.3(3) . . . . ?
C6 C1 C14 C15 -179.7(2) . . . . ?
C13 C14 C15 C16 116.8(3) . . . . ?
C1 C14 C15 C16 -65.1(3) . . . . ?
C14 C15 C16 C17 -177.9(2) . . . . ?
C14 C15 C16 C24 -4.2(4) . . . . ?
C15 C16 C17 O1 -6.7(4) . . . . ?
C24 C16 C17 O1 178.6(3) . . . . ?
C15 C16 C17 C18 172.8(2) . . . . ?
C24 C16 C17 C18 -2.0(3) . . . . ?
O1 C17 C18 C23 179.4(2) . . . . ?
C16 C17 C18 C23 0.0(3) . . . . ?
O1 C17 C18 C19 1.8(4) . . . . ?
C16 C17 C18 C19 -177.7(2) . . . . ?
C23 C18 C19 C20 -0.6(4) . . . . ?
C17 C18 C19 C20 176.9(2) . . . . ?
C18 C19 C20 C21 0.1(4) . . . . ?
C19 C20 C21 C22 0.1(4) . . . . ?
C20 C21 C22 C23 0.2(4) . . . . ?
C21 C22 C23 C18 -0.7(4) . . . . ?
C21 C22 C23 C24 -179.5(3) . . . . ?
C19 C18 C23 C22 0.9(3) . . . . ?
C17 C18 C23 C22 -177.0(2) . . . . ?
C19 C18 C23 C24 179.9(2) . . . . ?
C17 C18 C23 C24 2.0(3) . . . . ?
C15 C16 C24 C23 -171.4(2) . . . . ?
C17 C16 C24 C23 3.0(3) . . . . ?
C22 C23 C24 C16 175.8(2) . . . . ?
C18 C23 C24 C16 -3.1(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2014/6


####################################################################### 
# 
# 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_anth_after_uv
_database_code_depnum_ccdc_archive 'CCDC 1482559'
_audit_update_record             
;
2016-05-30 deposited with the CCDC.
2016-06-16 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24 H16 O'
_chemical_formula_moiety         'C24 H16 O'
_chemical_formula_weight         320.39
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 -1/2-X,-1/2+Y,+Z
7 +X,-1/2-Y,-1/2+Z
8 -1/2+X,+Y,-1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   14.6653(16)
_cell_length_b                   8.6929(10)
_cell_length_c                   25.929(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     3305.5(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8860
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      27.47
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344.00
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.504
_exptl_absorpt_correction_T_max  0.992

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            27195
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         3.143
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3629
_reflns_number_gt                2417
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.0773
_refine_ls_wR_factor_ref         0.1505
_refine_ls_wR_factor_gt          0.1330
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         3629
_refine_ls_number_parameters     290
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0413P)²+1.4690P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.15
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 -0.06906(12) -0.4012(2) 0.33261(7) 0.0679(5) Uani 1 1 d . . . . .
C1 C 0.09719(15) -0.1518(3) 0.49180(9) 0.0522(6) Uani 1 1 d . . . . .
C2 C 0.07784(18) -0.3047(3) 0.50805(11) 0.0606(7) Uani 1 1 d . . . . .
C3 C 0.0987(2) -0.3541(4) 0.55606(12) 0.0723(8) Uani 1 1 d . . . . .
C4 C 0.1428(2) -0.2544(5) 0.59118(12) 0.0767(9) Uani 1 1 d . . . . .
C5 C 0.1644(2) -0.1100(5) 0.57722(11) 0.0713(8) Uani 1 1 d . . . . .
C6 C 0.14269(16) -0.0524(3) 0.52746(9) 0.0559(7) Uani 1 1 d . . . . .
C7 C 0.16446(17) 0.0977(3) 0.51244(11) 0.0602(7) Uani 1 1 d . . . . .
C8 C 0.14313(15) 0.1535(3) 0.46410(10) 0.0540(6) Uani 1 1 d . . . . .
C9 C 0.16329(19) 0.3096(3) 0.44912(14) 0.0666(8) Uani 1 1 d . . . . .
C10 C 0.1405(2) 0.3633(4) 0.40291(14) 0.0723(8) Uani 1 1 d . . . . .
C11 C 0.0943(2) 0.2680(3) 0.36740(13) 0.0707(8) Uani 1 1 d . . . . .
C12 C 0.07357(19) 0.1200(3) 0.37964(11) 0.0602(7) Uani 1 1 d . . . . .
C13 C 0.09719(15) 0.0559(3) 0.42814(9) 0.0514(6) Uani 1 1 d . . . . .
C14 C 0.07587(15) -0.0965(3) 0.44240(9) 0.0498(6) Uani 1 1 d . . . . .
C15 C 0.02767(18) -0.1999(3) 0.40555(10) 0.0519(6) Uani 1 1 d . . . . .
C16 C 0.06048(16) -0.2501(3) 0.36109(9) 0.0507(6) Uani 1 1 d . . . . .
C17 C 0.15393(19) -0.2245(4) 0.33882(11) 0.0611(7) Uani 1 1 d . . . . .
C18 C 0.15598(17) -0.3285(3) 0.29239(9) 0.0523(6) Uani 1 1 d . . . . .
C19 C 0.2276(2) -0.3584(3) 0.25908(10) 0.0624(7) Uani 1 1 d . . . . .
C20 C 0.2143(2) -0.4594(4) 0.21897(10) 0.0682(8) Uani 1 1 d . . . . .
C21 C 0.1309(2) -0.5314(4) 0.21156(10) 0.0681(8) Uani 1 1 d . . . . .
C22 C 0.0595(2) -0.5034(3) 0.24439(10) 0.0582(7) Uani 1 1 d . . . . .
C23 C 0.07255(17) -0.4019(3) 0.28523(8) 0.0488(6) Uani 1 1 d . . . . .
C24 C 0.00952(17) -0.3585(3) 0.32676(9) 0.0504(6) Uani 1 1 d . . . . .
H2 H 0.0517(15) -0.373(3) 0.4843(9) 0.051(7) Uiso 1 1 d . . . . .
H3 H 0.0859(19) -0.462(4) 0.5654(11) 0.086(10) Uiso 1 1 d . . . . .
H4 H 0.157(2) -0.287(4) 0.6263(13) 0.096(10) Uiso 1 1 d . . . . .
H5 H 0.1946(19) -0.043(3) 0.6022(11) 0.084(9) Uiso 1 1 d . . . . .
H7 H 0.1926(17) 0.166(3) 0.5375(10) 0.072(8) Uiso 1 1 d . . . . .
H9 H 0.1917(17) 0.362(3) 0.4751(10) 0.063(8) Uiso 1 1 d . . . . .
H10 H 0.155(2) 0.480(4) 0.3907(12) 0.109(11) Uiso 1 1 d . . . . .
H11 H 0.078(2) 0.312(4) 0.3314(12) 0.103(11) Uiso 1 1 d . . . . .
H12 H 0.0401(16) 0.057(3) 0.3554(10) 0.065(8) Uiso 1 1 d . . . . .
H15 H -0.0343(17) -0.231(3) 0.4148(9) 0.059(7) Uiso 1 1 d . . . . .
H17A H 0.1626(19) -0.114(4) 0.3282(11) 0.091(10) Uiso 1 1 d . . . . .
H17B H 0.2004(18) -0.250(3) 0.3625(10) 0.076(9) Uiso 1 1 d . . . . .
H19 H 0.2882(19) -0.311(3) 0.2660(10) 0.076(9) Uiso 1 1 d . . . . .
H20 H 0.265(2) -0.483(3) 0.1954(12) 0.095(10) Uiso 1 1 d . . . . .
H21 H 0.1229(17) -0.604(3) 0.1814(10) 0.070(8) Uiso 1 1 d . . . . .
H22 H 0.0016(18) -0.551(3) 0.2427(9) 0.056(7) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL Version 2014/6 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C24 1.220(3) . ?
C1 C14 1.403(3) . ?
C1 C2 1.423(4) . ?
C1 C6 1.430(3) . ?
C2 C3 1.352(4) . ?
C2 H2 0.94(2) . ?
C3 C4 1.414(5) . ?
C3 H3 0.99(3) . ?
C4 C5 1.344(5) . ?
C4 H4 0.98(3) . ?
C5 C6 1.420(4) . ?
C5 H5 0.98(3) . ?
C6 C7 1.398(4) . ?
C7 C8 1.380(4) . ?
C7 H7 0.97(3) . ?
C8 C13 1.429(3) . ?
C8 C9 1.443(4) . ?
C9 C10 1.328(4) . ?
C9 H9 0.92(2) . ?
C10 C11 1.412(4) . ?
C10 H10 1.09(3) . ?
C11 C12 1.359(4) . ?
C11 H11 1.04(3) . ?
C12 C13 1.418(4) . ?
C12 H12 0.97(2) . ?
C13 C14 1.411(3) . ?
C14 C15 1.490(3) . ?
C15 C16 1.323(3) . ?
C15 H15 0.98(2) . ?
C16 C24 1.496(3) . ?
C16 C17 1.504(4) . ?
C17 C18 1.506(3) . ?
C17 H17A 1.01(3) . ?
C17 H17B 0.94(3) . ?
C18 C19 1.385(3) . ?
C18 C23 1.392(3) . ?
C19 C20 1.375(4) . ?
C19 H19 1.00(3) . ?
C20 C21 1.387(4) . ?
C20 H20 0.98(3) . ?
C21 C22 1.371(4) . ?
C21 H21 1.01(3) . ?
C22 C23 1.392(3) . ?
C22 H22 0.94(3) . ?
C23 C24 1.468(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 C1 C2 123.1(2) . . ?
C14 C1 C6 119.2(2) . . ?
C2 C1 C6 117.8(2) . . ?
C3 C2 C1 121.6(3) . . ?
C3 C2 H2 119.8(14) . . ?
C1 C2 H2 118.6(14) . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 119.0(18) . . ?
C4 C3 H3 120.7(17) . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 118.2(19) . . ?
C3 C4 H4 121.3(19) . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5 119.1(17) . . ?
C6 C5 H5 119.5(17) . . ?
C7 C6 C5 122.0(3) . . ?
C7 C6 C1 119.3(2) . . ?
C5 C6 C1 118.6(3) . . ?
C8 C7 C6 121.9(2) . . ?
C8 C7 H7 119.2(16) . . ?
C6 C7 H7 118.8(16) . . ?
C7 C8 C13 119.4(3) . . ?
C7 C8 C9 121.9(3) . . ?
C13 C8 C9 118.6(3) . . ?
C10 C9 C8 121.5(3) . . ?
C10 C9 H9 127.0(17) . . ?
C8 C9 H9 111.5(16) . . ?
C9 C10 C11 120.2(3) . . ?
C9 C10 H10 122.8(17) . . ?
C11 C10 H10 117.0(17) . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 120.6(18) . . ?
C10 C11 H11 118.7(18) . . ?
C11 C12 C13 121.6(3) . . ?
C11 C12 H12 119.7(15) . . ?
C13 C12 H12 118.7(15) . . ?
C14 C13 C12 123.2(2) . . ?
C14 C13 C8 119.4(2) . . ?
C12 C13 C8 117.4(2) . . ?
C1 C14 C13 120.8(2) . . ?
C1 C14 C15 119.0(2) . . ?
C13 C14 C15 120.2(2) . . ?
C16 C15 C14 125.8(2) . . ?
C16 C15 H15 117.3(14) . . ?
C14 C15 H15 116.8(14) . . ?
C15 C16 C24 123.0(2) . . ?
C15 C16 C17 128.1(2) . . ?
C24 C16 C17 108.7(2) . . ?
C16 C17 C18 103.7(2) . . ?
C16 C17 H17A 111.1(17) . . ?
C18 C17 H17A 110.7(17) . . ?
C16 C17 H17B 111.9(16) . . ?
C18 C17 H17B 111.3(17) . . ?
H17A C17 H17B 108(2) . . ?
C19 C18 C23 119.9(2) . . ?
C19 C18 C17 128.8(2) . . ?
C23 C18 C17 111.4(2) . . ?
C20 C19 C18 118.9(3) . . ?
C20 C19 H19 122.0(15) . . ?
C18 C19 H19 119.0(15) . . ?
C19 C20 C21 121.3(3) . . ?
C19 C20 H20 120.0(18) . . ?
C21 C20 H20 118.8(17) . . ?
C22 C21 C20 120.4(3) . . ?
C22 C21 H21 120.0(15) . . ?
C20 C21 H21 119.5(15) . . ?
C21 C22 C23 118.7(3) . . ?
C21 C22 H22 125.5(15) . . ?
C23 C22 H22 115.7(14) . . ?
C22 C23 C18 120.8(2) . . ?
C22 C23 C24 129.4(2) . . ?
C18 C23 C24 109.7(2) . . ?
O1 C24 C23 127.4(2) . . ?
O1 C24 C16 126.1(2) . . ?
C23 C24 C16 106.5(2) . . ?

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 -179.5(2) . . . . ?
C6 C1 C2 C3 2.2(4) . . . . ?
C1 C2 C3 C4 -1.5(4) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C3 C4 C5 C6 1.0(5) . . . . ?
C4 C5 C6 C7 179.8(3) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C14 C1 C6 C7 0.3(3) . . . . ?
C2 C1 C6 C7 178.7(2) . . . . ?
C14 C1 C6 C5 -179.6(2) . . . . ?
C2 C1 C6 C5 -1.2(3) . . . . ?
C5 C6 C7 C8 -179.9(2) . . . . ?
C1 C6 C7 C8 0.2(4) . . . . ?
C6 C7 C8 C13 0.2(4) . . . . ?
C6 C7 C8 C9 178.2(2) . . . . ?
C7 C8 C9 C10 -178.4(3) . . . . ?
C13 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C11 1.0(4) . . . . ?
C9 C10 C11 C12 -0.8(4) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C11 C12 C13 C14 179.3(2) . . . . ?
C11 C12 C13 C8 0.6(4) . . . . ?
C7 C8 C13 C14 -1.1(3) . . . . ?
C9 C8 C13 C14 -179.2(2) . . . . ?
C7 C8 C13 C12 177.7(2) . . . . ?
C9 C8 C13 C12 -0.4(3) . . . . ?
C2 C1 C14 C13 -179.5(2) . . . . ?
C6 C1 C14 C13 -1.3(3) . . . . ?
C2 C1 C14 C15 2.3(3) . . . . ?
C6 C1 C14 C15 -179.4(2) . . . . ?
C12 C13 C14 C1 -177.0(2) . . . . ?
C8 C13 C14 C1 1.6(3) . . . . ?
C12 C13 C14 C15 1.1(4) . . . . ?
C8 C13 C14 C15 179.8(2) . . . . ?
C1 C14 C15 C16 -116.6(3) . . . . ?
C13 C14 C15 C16 65.2(3) . . . . ?
C14 C15 C16 C24 177.7(2) . . . . ?
C14 C15 C16 C17 4.1(4) . . . . ?
C15 C16 C17 C18 171.4(3) . . . . ?
C24 C16 C17 C18 -3.0(3) . . . . ?
C16 C17 C18 C19 -175.7(3) . . . . ?
C16 C17 C18 C23 3.2(3) . . . . ?
C23 C18 C19 C20 0.7(4) . . . . ?
C17 C18 C19 C20 179.5(3) . . . . ?
C18 C19 C20 C21 -0.2(4) . . . . ?
C19 C20 C21 C22 -0.1(5) . . . . ?
C20 C21 C22 C23 -0.2(4) . . . . ?
C21 C22 C23 C18 0.8(4) . . . . ?
C21 C22 C23 C24 -176.7(2) . . . . ?
C19 C18 C23 C22 -1.1(4) . . . . ?
C17 C18 C23 C22 180.0(2) . . . . ?
C19 C18 C23 C24 176.9(2) . . . . ?
C17 C18 C23 C24 -2.1(3) . . . . ?
C22 C23 C24 O1 -2.3(4) . . . . ?
C18 C23 C24 O1 -180.0(2) . . . . ?
C22 C23 C24 C16 177.8(2) . . . . ?
C18 C23 C24 C16 0.1(3) . . . . ?
C15 C16 C24 O1 7.3(4) . . . . ?
C17 C16 C24 O1 -178.0(3) . . . . ?
C15 C16 C24 C23 -172.8(2) . . . . ?
C17 C16 C24 C23 1.9(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2014/6


