# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2018

####################################################################### 
# 
# 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_0378_290114_mh_monobnzylpyr_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1kblhz
_database_code_depnum_ccdc_archive 'CCDC 1440151'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C6CE00610H 2016
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        phenyl(pyren-1-yl)methanone
_chemical_name_common            monobenzoylpyrene
_chemical_melting_point          375.15
_chemical_formula_moiety         'C23 H14 O'
_chemical_formula_sum            'C23 H14 O'
_chemical_formula_weight         306.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '
_symmetry_space_group_name_Hall  '-P 1  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0024(2)
_cell_length_b                   9.6519(3)
_cell_length_c                   10.0837(3)
_cell_angle_alpha                102.8140(10)
_cell_angle_beta                 96.5760(10)
_cell_angle_gamma                91.4730(10)
_cell_volume                     753.40(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6698
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      28.31

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      1.349
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9840
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11056
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2644
_reflns_number_gt                2262
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0898P)²+0.0757P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2644
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1458
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      1.151
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.25178(16) 0.14214(14) 0.31530(14) 0.0395(3) Uani 1 1 d . . .
C2 C 0.35188(18) 0.12608(15) 0.43254(15) 0.0461(4) Uani 1 1 d . . .
H2 H 0.3922 0.0372 0.4357 0.055 Uiso 1 1 calc R . .
C3 C 0.39311(18) 0.23786(16) 0.54399(14) 0.0466(4) Uani 1 1 d . . .
H3 H 0.4594 0.2234 0.6212 0.056 Uiso 1 1 calc R . .
C4 C 0.37583(18) 0.49179(16) 0.65577(14) 0.0482(4) Uani 1 1 d . . .
H4 H 0.4438 0.4798 0.7332 0.058 Uiso 1 1 calc R . .
C5 C 0.31703(19) 0.61984(16) 0.65307(15) 0.0510(4) Uani 1 1 d . . .
H5 H 0.3433 0.6943 0.7295 0.061 Uiso 1 1 calc R . .
C6 C 0.1523(2) 0.77777(15) 0.53063(17) 0.0539(4) Uani 1 1 d . . .
H6 H 0.1770 0.8536 0.6061 0.065 Uiso 1 1 calc R . .
C7 C 0.0547(2) 0.79810(15) 0.41571(18) 0.0570(4) Uani 1 1 d . . .
H7 H 0.0150 0.8875 0.4141 0.068 Uiso 1 1 calc R . .
C8 C 0.01517(19) 0.68701(15) 0.30271(17) 0.0511(4) Uani 1 1 d . . .
H8 H -0.0513 0.7023 0.2259 0.061 Uiso 1 1 calc R . .
C9 C 0.03455(18) 0.43309(15) 0.18851(14) 0.0450(4) Uani 1 1 d . . .
H9 H -0.0302 0.4467 0.1102 0.054 Uiso 1 1 calc R . .
C10 C 0.08803(17) 0.30216(14) 0.19067(14) 0.0417(3) Uani 1 1 d . . .
H10 H 0.0583 0.2276 0.1148 0.050 Uiso 1 1 calc R . .
C11 C 0.19030(15) 0.27630(13) 0.30856(13) 0.0360(3) Uani 1 1 d . . .
C12 C 0.23439(15) 0.39263(13) 0.42299(13) 0.0358(3) Uani 1 1 d . . .
C13 C 0.33606(16) 0.37249(15) 0.54160(13) 0.0400(3) Uani 1 1 d . . .
C14 C 0.17515(16) 0.53010(14) 0.42017(14) 0.0375(3) Uani 1 1 d . . .
C15 C 0.07394(16) 0.55189(14) 0.30244(14) 0.0415(3) Uani 1 1 d . . .
C16 C 0.21490(17) 0.64506(14) 0.53581(15) 0.0438(4) Uani 1 1 d . . .
C17 C 0.20529(16) 0.01247(14) 0.20285(14) 0.0406(3) Uani 1 1 d . . .
C18 C 0.34268(16) -0.08064(13) 0.15359(13) 0.0386(3) Uani 1 1 d . . .
C19 C 0.30019(19) -0.22038(15) 0.08437(14) 0.0482(4) Uani 1 1 d . . .
H19 H 0.1889 -0.2554 0.0730 0.058 Uiso 1 1 calc R . .
C20 C 0.4222(2) -0.30739(17) 0.03246(16) 0.0599(4) Uani 1 1 d . . .
H20 H 0.3929 -0.4012 -0.0129 0.072 Uiso 1 1 calc R . .
C21 C 0.5863(2) -0.25666(18) 0.04715(16) 0.0609(5) Uani 1 1 d . . .
H21 H 0.6678 -0.3159 0.0111 0.073 Uiso 1 1 calc R . .
C22 C 0.63094(19) -0.11818(18) 0.11513(16) 0.0572(4) Uani 1 1 d . . .
H22 H 0.7423 -0.0836 0.1248 0.069 Uiso 1 1 calc R . .
C23 C 0.50922(17) -0.03087(15) 0.16889(15) 0.0477(4) Uani 1 1 d . . .
H23 H 0.5396 0.0623 0.2158 0.057 Uiso 1 1 calc R . .
O1 O 0.05984(12) -0.01886(11) 0.15347(11) 0.0574(3) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3907(19) . ?
C1 C11 1.4098(18) . ?
C1 C17 1.4968(18) . ?
C2 C3 1.377(2) . ?
C2 H2 0.9300 . ?
C3 C13 1.393(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.338(2) . ?
C4 C13 1.4359(19) . ?
C4 H4 0.9300 . ?
C5 C16 1.429(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(2) . ?
C6 C16 1.397(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.381(2) . ?
C7 H7 0.9300 . ?
C8 C15 1.3973(19) . ?
C8 H8 0.9300 . ?
C9 C10 1.3485(19) . ?
C9 C15 1.4312(19) . ?
C9 H9 0.9300 . ?
C10 C11 1.4369(18) . ?
C10 H10 0.9300 . ?
C11 C12 1.4242(18) . ?
C12 C13 1.4208(19) . ?
C12 C14 1.4255(19) . ?
C14 C15 1.4173(19) . ?
C14 C16 1.4195(19) . ?
C17 O1 1.2151(16) . ?
C17 C18 1.4970(18) . ?
C18 C23 1.3849(19) . ?
C18 C19 1.3880(19) . ?
C19 C20 1.377(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.371(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.377(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.383(2) . ?
C22 H22 0.9300 . ?
C23 H23 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 C11 119.74(12) . . ?
C2 C1 C17 117.98(12) . . ?
C11 C1 C17 122.19(12) . . ?
C3 C2 C1 121.94(13) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C13 120.31(13) . . ?
C2 C3 H3 119.8 . . ?
C13 C3 H3 119.8 . . ?
C5 C4 C13 121.36(14) . . ?
C5 C4 H4 119.3 . . ?
C13 C4 H4 119.3 . . ?
C4 C5 C16 121.73(13) . . ?
C4 C5 H5 119.1 . . ?
C16 C5 H5 119.1 . . ?
C7 C6 C16 121.07(14) . . ?
C7 C6 H6 119.5 . . ?
C16 C6 H6 119.5 . . ?
C6 C7 C8 120.62(14) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C15 120.74(15) . . ?
C7 C8 H8 119.6 . . ?
C15 C8 H8 119.6 . . ?
C10 C9 C15 122.33(13) . . ?
C10 C9 H9 118.8 . . ?
C15 C9 H9 118.8 . . ?
C9 C10 C11 120.90(13) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C1 C11 C12 118.49(12) . . ?
C1 C11 C10 123.19(12) . . ?
C12 C11 C10 118.30(12) . . ?
C13 C12 C11 120.37(12) . . ?
C13 C12 C14 119.37(12) . . ?
C11 C12 C14 120.25(12) . . ?
C3 C13 C12 119.14(12) . . ?
C3 C13 C4 122.06(13) . . ?
C12 C13 C4 118.80(13) . . ?
C15 C14 C16 119.74(12) . . ?
C15 C14 C12 120.01(12) . . ?
C16 C14 C12 120.24(13) . . ?
C8 C15 C14 119.04(13) . . ?
C8 C15 C9 122.76(13) . . ?
C14 C15 C9 118.19(12) . . ?
C6 C16 C14 118.80(14) . . ?
C6 C16 C5 122.73(13) . . ?
C14 C16 C5 118.48(13) . . ?
O1 C17 C1 121.45(12) . . ?
O1 C17 C18 120.20(12) . . ?
C1 C17 C18 118.33(11) . . ?
C23 C18 C19 118.77(12) . . ?
C23 C18 C17 122.51(12) . . ?
C19 C18 C17 118.65(12) . . ?
C20 C19 C18 120.28(14) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 120.45(14) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 120.14(14) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C23 119.62(14) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C22 C23 C18 120.72(13) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 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
C11 C1 C2 C3 0.3(2) . . . . ?
C17 C1 C2 C3 -176.38(12) . . . . ?
C1 C2 C3 C13 -0.7(2) . . . . ?
C13 C4 C5 C16 -1.3(2) . . . . ?
C16 C6 C7 C8 0.5(2) . . . . ?
C6 C7 C8 C15 -0.3(2) . . . . ?
C15 C9 C10 C11 -0.8(2) . . . . ?
C2 C1 C11 C12 0.5(2) . . . . ?
C17 C1 C11 C12 177.02(10) . . . . ?
C2 C1 C11 C10 179.19(11) . . . . ?
C17 C1 C11 C10 -4.3(2) . . . . ?
C9 C10 C11 C1 -178.93(12) . . . . ?
C9 C10 C11 C12 -0.2(2) . . . . ?
C1 C11 C12 C13 -0.91(19) . . . . ?
C10 C11 C12 C13 -179.65(11) . . . . ?
C1 C11 C12 C14 179.86(10) . . . . ?
C10 C11 C12 C14 1.11(19) . . . . ?
C2 C3 C13 C12 0.2(2) . . . . ?
C2 C3 C13 C4 179.84(12) . . . . ?
C11 C12 C13 C3 0.54(19) . . . . ?
C14 C12 C13 C3 179.78(11) . . . . ?
C11 C12 C13 C4 -179.07(11) . . . . ?
C14 C12 C13 C4 0.17(19) . . . . ?
C5 C4 C13 C3 -178.53(13) . . . . ?
C5 C4 C13 C12 1.1(2) . . . . ?
C13 C12 C14 C15 179.86(10) . . . . ?
C11 C12 C14 C15 -0.90(19) . . . . ?
C13 C12 C14 C16 -1.14(19) . . . . ?
C11 C12 C14 C16 178.10(10) . . . . ?
C7 C8 C15 C14 0.0(2) . . . . ?
C7 C8 C15 C9 179.17(12) . . . . ?
C16 C14 C15 C8 0.04(19) . . . . ?
C12 C14 C15 C8 179.05(11) . . . . ?
C16 C14 C15 C9 -179.17(11) . . . . ?
C12 C14 C15 C9 -0.16(19) . . . . ?
C10 C9 C15 C8 -178.13(13) . . . . ?
C10 C9 C15 C14 1.1(2) . . . . ?
C7 C6 C16 C14 -0.4(2) . . . . ?
C7 C6 C16 C5 179.81(13) . . . . ?
C15 C14 C16 C6 0.17(19) . . . . ?
C12 C14 C16 C6 -178.84(11) . . . . ?
C15 C14 C16 C5 179.93(11) . . . . ?
C12 C14 C16 C5 0.93(19) . . . . ?
C4 C5 C16 C6 -179.94(13) . . . . ?
C4 C5 C16 C14 0.3(2) . . . . ?
C2 C1 C17 O1 128.56(15) . . . . ?
C11 C1 C17 O1 -48.01(19) . . . . ?
C2 C1 C17 C18 -50.26(17) . . . . ?
C11 C1 C17 C18 133.17(13) . . . . ?
O1 C17 C18 C23 157.56(14) . . . . ?
C1 C17 C18 C23 -23.60(18) . . . . ?
O1 C17 C18 C19 -19.4(2) . . . . ?
C1 C17 C18 C19 159.45(12) . . . . ?
C23 C18 C19 C20 0.2(2) . . . . ?
C17 C18 C19 C20 177.23(13) . . . . ?
C18 C19 C20 C21 -0.7(2) . . . . ?
C19 C20 C21 C22 0.5(3) . . . . ?
C20 C21 C22 C23 0.2(3) . . . . ?
C21 C22 C23 C18 -0.8(2) . . . . ?
C19 C18 C23 C22 0.6(2) . . . . ?
C17 C18 C23 C22 -176.33(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.136
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3:Acetone'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1559464'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 O'
_chemical_formula_weight         282.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.3434(7)
_cell_length_b                   6.0678(4)
_cell_length_c                   14.7523(12)
_cell_angle_alpha                90
_cell_angle_beta                 103.178(4)
_cell_angle_gamma                90
_cell_volume                     727.18(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2643
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      24.97

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.289
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9846
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            6306
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.584
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 0.949
_reflns_number_total             2696
_reflns_number_gt                2206
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_max     0.869
_reflns_Friedel_fraction_full    0.888

_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0626P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 839 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   2.2(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2696
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0929
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.965
_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 0.4531(2) 0.0734(4) 0.24810(15) 0.0451(6) Uani 1 1 d . . . . .
C2 C 0.5045(3) 0.2489(4) 0.18962(14) 0.0447(5) Uani 1 1 d . . . . .
C3 C 0.3977(3) 0.4206(5) 0.16196(17) 0.0616(7) Uani 1 1 d . . . . .
H3 H 0.2986 0.4238 0.1807 0.074 Uiso 1 1 calc R U . . .
C4 C 0.4344(5) 0.5901(5) 0.1064(2) 0.0818(10) Uani 1 1 d . . . . .
H4 H 0.3598 0.7046 0.0883 0.098 Uiso 1 1 calc R U . . .
C5 C 0.5769(5) 0.5887(5) 0.07897(19) 0.0828(10) Uani 1 1 d . . . . .
H5 H 0.6000 0.7033 0.0421 0.099 Uiso 1 1 calc R U . . .
C6 C 0.6924(4) 0.4172(5) 0.10486(16) 0.0627(8) Uani 1 1 d . . . . .
C7 C 0.8434(5) 0.4099(7) 0.07588(19) 0.0869(12) Uani 1 1 d . . . . .
H7 H 0.8699 0.5246 0.0401 0.104 Uiso 1 1 calc R U . . .
C8 C 0.9492(4) 0.2400(9) 0.0992(2) 0.0912(12) Uani 1 1 d . . . . .
H8 H 1.0482 0.2403 0.0803 0.109 Uiso 1 1 calc R U . . .
C9 C 0.9116(3) 0.0648(6) 0.15134(19) 0.0719(9) Uani 1 1 d . . . . .
H9 H 0.9840 -0.0533 0.1657 0.086 Uiso 1 1 calc R U . . .
C10 C 0.7694(3) 0.0653(4) 0.18146(16) 0.0530(6) Uani 1 1 d . . . . .
H10 H 0.7460 -0.0525 0.2167 0.064 Uiso 1 1 calc R U . . .
C11 C 0.6562(3) 0.2418(4) 0.16021(13) 0.0438(5) Uani 1 1 d . . . . .
C12 C 0.5579(2) 0.0143(4) 0.34008(14) 0.0394(5) Uani 1 1 d . . . . .
C13 C 0.6735(2) 0.1579(4) 0.38793(14) 0.0368(5) Uani 1 1 d . . . . .
H13 H 0.6927 0.2895 0.3599 0.044 Uiso 1 1 calc R U . . .
C14 C 0.7642(2) 0.1102(3) 0.47894(14) 0.0358(5) Uani 1 1 d . . . . .
C15 C 0.8801(3) 0.2579(4) 0.53034(15) 0.0442(5) Uani 1 1 d . . . . .
H15 H 0.8994 0.3917 0.5040 0.053 Uiso 1 1 calc R U . . .
C16 C 0.9640(3) 0.2073(5) 0.61801(16) 0.0561(7) Uani 1 1 d . . . . .
H16 H 1.0401 0.3066 0.6512 0.067 Uiso 1 1 calc R U . . .
C17 C 0.9363(3) 0.0055(5) 0.65886(16) 0.0599(7) Uani 1 1 d . . . . .
H17 H 0.9944 -0.0278 0.7189 0.072 Uiso 1 1 calc R U . . .
C18 C 0.8258(3) -0.1406(4) 0.61134(16) 0.0520(7) Uani 1 1 d . . . . .
H18 H 0.8090 -0.2734 0.6392 0.062 Uiso 1 1 calc R U . . .
C19 C 0.7357(3) -0.0943(4) 0.52017(15) 0.0395(5) Uani 1 1 d . . . . .
C20 C 0.6178(3) -0.2405(4) 0.46819(16) 0.0465(6) Uani 1 1 d . . . . .
H20 H 0.5999 -0.3760 0.4937 0.056 Uiso 1 1 calc R U . . .
C21 C 0.5306(3) -0.1873(4) 0.38215(16) 0.0460(6) Uani 1 1 d . . . . .
H21 H 0.4516 -0.2847 0.3501 0.055 Uiso 1 1 calc R U . . .
O1 O 0.31824(19) -0.0133(4) 0.22157(12) 0.0701(6) 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
C1 O1 1.223(3) . ?
C1 C12 1.481(3) . ?
C1 C2 1.494(3) . ?
C2 C3 1.371(3) . ?
C2 C11 1.429(3) . ?
C3 C4 1.392(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.341(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.411(5) . ?
C5 H5 0.9300 . ?
C6 C11 1.415(3) . ?
C6 C7 1.420(5) . ?
C7 C8 1.350(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.389(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.359(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.415(3) . ?
C10 H10 0.9300 . ?
C12 C13 1.370(3) . ?
C12 C21 1.414(3) . ?
C13 C14 1.413(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.407(3) . ?
C14 C19 1.425(3) . ?
C15 C16 1.358(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.407(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.354(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.411(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.414(3) . ?
C20 C21 1.350(3) . ?
C20 H20 0.9300 . ?
C21 H21 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
O1 C1 C12 119.8(2) . . ?
O1 C1 C2 119.1(2) . . ?
C12 C1 C2 120.94(18) . . ?
C3 C2 C11 119.6(2) . . ?
C3 C2 C1 117.4(2) . . ?
C11 C2 C1 123.02(19) . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C11 119.2(3) . . ?
C5 C6 C7 122.7(3) . . ?
C11 C6 C7 118.1(3) . . ?
C8 C7 C6 121.4(3) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 120.5(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 121.2(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C6 118.5(2) . . ?
C10 C11 C2 123.2(2) . . ?
C6 C11 C2 118.2(2) . . ?
C13 C12 C21 119.3(2) . . ?
C13 C12 C1 121.2(2) . . ?
C21 C12 C1 119.42(19) . . ?
C12 C13 C14 121.4(2) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 122.34(19) . . ?
C15 C14 C19 119.08(19) . . ?
C13 C14 C19 118.58(17) . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 120.5(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 121.0(2) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C18 C19 C20 123.1(2) . . ?
C18 C19 C14 118.37(19) . . ?
C20 C19 C14 118.57(18) . . ?
C21 C20 C19 121.2(2) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C12 120.9(2) . . ?
C20 C21 H21 119.5 . . ?
C12 C21 H21 119.5 . . ?

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
O1 C1 C2 C3 51.7(3) . . . . ?
C12 C1 C2 C3 -124.2(2) . . . . ?
O1 C1 C2 C11 -126.8(2) . . . . ?
C12 C1 C2 C11 57.3(3) . . . . ?
C11 C2 C3 C4 -0.7(3) . . . . ?
C1 C2 C3 C4 -179.2(2) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C11 0.6(4) . . . . ?
C4 C5 C6 C7 179.2(3) . . . . ?
C5 C6 C7 C8 -177.8(3) . . . . ?
C11 C6 C7 C8 0.7(4) . . . . ?
C6 C7 C8 C9 1.1(4) . . . . ?
C7 C8 C9 C10 -1.7(4) . . . . ?
C8 C9 C10 C11 0.5(4) . . . . ?
C9 C10 C11 C6 1.3(3) . . . . ?
C9 C10 C11 C2 179.5(2) . . . . ?
C5 C6 C11 C10 176.7(2) . . . . ?
C7 C6 C11 C10 -1.9(3) . . . . ?
C5 C6 C11 C2 -1.5(3) . . . . ?
C7 C6 C11 C2 179.9(2) . . . . ?
C3 C2 C11 C10 -176.6(2) . . . . ?
C1 C2 C11 C10 1.8(3) . . . . ?
C3 C2 C11 C6 1.5(3) . . . . ?
C1 C2 C11 C6 179.97(19) . . . . ?
O1 C1 C12 C13 -154.4(2) . . . . ?
C2 C1 C12 C13 21.5(3) . . . . ?
O1 C1 C12 C21 21.2(3) . . . . ?
C2 C1 C12 C21 -162.93(18) . . . . ?
C21 C12 C13 C14 -1.0(3) . . . . ?
C1 C12 C13 C14 174.63(17) . . . . ?
C12 C13 C14 C15 -178.11(19) . . . . ?
C12 C13 C14 C19 1.2(3) . . . . ?
C13 C14 C15 C16 179.40(19) . . . . ?
C19 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C17 0.1(4) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C16 C17 C18 C19 -0.1(4) . . . . ?
C17 C18 C19 C20 -179.3(2) . . . . ?
C17 C18 C19 C14 0.2(3) . . . . ?
C15 C14 C19 C18 -0.2(3) . . . . ?
C13 C14 C19 C18 -179.6(2) . . . . ?
C15 C14 C19 C20 179.4(2) . . . . ?
C13 C14 C19 C20 0.0(2) . . . . ?
C18 C19 C20 C21 178.0(2) . . . . ?
C14 C19 C20 C21 -1.5(3) . . . . ?
C19 C20 C21 C12 1.8(3) . . . . ?
C13 C12 C21 C20 -0.6(3) . . . . ?
C1 C12 C21 C20 -176.2(2) . . . . ?

_refine_diff_density_max         0.096
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.027

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1559462'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H12 O'
_chemical_formula_sum            'C17 H12 O'
_chemical_formula_weight         232.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.215(5)
_cell_length_b                   12.803(5)
_cell_length_c                   15.398(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1225.2(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4383
_cell_measurement_theta_min      3.28
_cell_measurement_theta_max      28.12

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.259
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9848
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            5796
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.646
_diffrn_reflns_theta_max         25.975
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             2339
_reflns_number_gt                2190
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_max     0.944
_reflns_Friedel_fraction_full    0.947

_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0428P)²+0.1634P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 861 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.8(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2339
_refine_ls_number_parameters     163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0930
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.074
_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 0.2556(5) 0.09297(19) 1.30550(15) 0.0705(7) Uani 1 1 d . . . . .
H1 H 0.1438 0.0966 1.3456 0.085 Uiso 1 1 calc R U . . .
C2 C 0.4255(5) 0.1568(2) 1.31470(15) 0.0731(7) Uani 1 1 d . . . . .
H2 H 0.4299 0.2047 1.3601 0.088 Uiso 1 1 calc R U . . .
C3 C 0.5944(5) 0.15100(18) 1.25597(15) 0.0655(6) Uani 1 1 d . . . . .
H3 H 0.7135 0.1940 1.2634 0.079 Uiso 1 1 calc R U . . .
C4 C 0.5890(4) 0.08316(15) 1.18733(13) 0.0506(5) Uani 1 1 d . . . . .
H4 H 0.7041 0.0813 1.1488 0.061 Uiso 1 1 calc R U . . .
C5 C 0.4117(3) 0.01592(14) 1.17401(12) 0.0460(4) Uani 1 1 d . . . . .
C6 C 0.2421(4) 0.01970(17) 1.23589(14) 0.0578(5) Uani 1 1 d . . . . .
C7 C 0.0681(4) -0.0490(2) 1.22700(19) 0.0750(6) Uani 1 1 d . U . . .
H7 H -0.0443 -0.0461 1.2668 0.090 Uiso 1 1 calc R U . . .
C8 C 0.0606(4) -0.1196(2) 1.1617(2) 0.0786(7) Uani 1 1 d . U . . .
H8 H -0.0550 -0.1655 1.1580 0.094 Uiso 1 1 calc R U . . .
C9 C 0.2266(4) -0.12421(17) 1.09900(17) 0.0682(7) Uani 1 1 d . . . . .
H9 H 0.2194 -0.1730 1.0543 0.082 Uiso 1 1 calc R U . . .
C10 C 0.3993(4) -0.05670(14) 1.10385(13) 0.0501(5) Uani 1 1 d . . . . .
C11 C 0.5643(4) -0.06156(14) 1.03328(14) 0.0544(5) Uani 1 1 d . . . . .
C12 C 0.6138(3) 0.03490(14) 0.98255(12) 0.0485(4) Uani 1 1 d . . . . .
C13 C 0.8081(4) 0.04339(19) 0.93892(14) 0.0616(6) Uani 1 1 d . . . . .
H13 H 0.9095 -0.0098 0.9432 0.074 Uiso 1 1 calc R U . . .
C14 C 0.8515(5) 0.1307(2) 0.88909(16) 0.0715(7) Uani 1 1 d . . . . .
H14 H 0.9827 0.1365 0.8605 0.086 Uiso 1 1 calc R U . . .
C15 C 0.7017(5) 0.2086(2) 0.88182(15) 0.0691(7) Uani 1 1 d . . . . .
H15 H 0.7309 0.2668 0.8476 0.083 Uiso 1 1 calc R U . . .
C16 C 0.5091(5) 0.20137(17) 0.92470(13) 0.0627(6) Uani 1 1 d . . . . .
H16 H 0.4084 0.2548 0.9197 0.075 Uiso 1 1 calc R U . . .
C17 C 0.4637(4) 0.11482(15) 0.97555(12) 0.0516(5) Uani 1 1 d . . . . .
H17 H 0.3333 0.1103 1.0049 0.062 Uiso 1 1 calc R U . . .
O1 O 0.6492(4) -0.14387(12) 1.01463(13) 0.0882(7) 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
C1 C2 1.343(4) . ?
C1 C6 1.427(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.387(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.413(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.422(3) . ?
C5 C10 1.427(3) . ?
C6 C7 1.400(4) . ?
C7 C8 1.352(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.415(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.496(3) . ?
C11 O1 1.213(2) . ?
C11 C12 1.493(3) . ?
C12 C13 1.386(3) . ?
C12 C17 1.389(3) . ?
C13 C14 1.382(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.370(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(3) . ?
C16 H16 0.9300 . ?
C17 H17 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 121.7(2) . . ?
C2 C1 H1 119.1 . . ?
C6 C1 H1 119.1 . . ?
C1 C2 C3 119.6(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 121.2(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 117.39(18) . . ?
C4 C5 C10 123.28(18) . . ?
C6 C5 C10 119.30(19) . . ?
C7 C6 C5 119.0(2) . . ?
C7 C6 C1 122.1(2) . . ?
C5 C6 C1 118.8(2) . . ?
C8 C7 C6 121.3(2) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 120.7(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C5 119.4(2) . . ?
C9 C10 C11 117.9(2) . . ?
C5 C10 C11 122.67(18) . . ?
O1 C11 C12 120.4(2) . . ?
O1 C11 C10 120.41(19) . . ?
C12 C11 C10 119.13(16) . . ?
C13 C12 C17 119.32(19) . . ?
C13 C12 C11 119.84(19) . . ?
C17 C12 C11 120.79(18) . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 120.3(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 119.8(2) . . ?
C16 C17 H17 120.1 . . ?
C12 C17 H17 120.1 . . ?

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 -0.9(3) . . . . ?
C1 C2 C3 C4 1.7(4) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 -1.6(3) . . . . ?
C3 C4 C5 C10 -179.50(19) . . . . ?
C4 C5 C6 C7 -177.20(18) . . . . ?
C10 C5 C6 C7 0.8(3) . . . . ?
C4 C5 C6 C1 2.3(3) . . . . ?
C10 C5 C6 C1 -179.68(18) . . . . ?
C2 C1 C6 C7 178.4(2) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C5 C6 C7 C8 1.0(3) . . . . ?
C1 C6 C7 C8 -178.5(2) . . . . ?
C6 C7 C8 C9 -1.6(4) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 C5 1.7(3) . . . . ?
C8 C9 C10 C11 -177.0(2) . . . . ?
C4 C5 C10 C9 175.74(18) . . . . ?
C6 C5 C10 C9 -2.1(3) . . . . ?
C4 C5 C10 C11 -5.7(3) . . . . ?
C6 C5 C10 C11 176.44(17) . . . . ?
C9 C10 C11 O1 -53.2(3) . . . . ?
C5 C10 C11 O1 128.2(2) . . . . ?
C9 C10 C11 C12 123.1(2) . . . . ?
C5 C10 C11 C12 -55.5(3) . . . . ?
O1 C11 C12 C13 -25.3(3) . . . . ?
C10 C11 C12 C13 158.33(18) . . . . ?
O1 C11 C12 C17 152.1(2) . . . . ?
C10 C11 C12 C17 -24.3(3) . . . . ?
C17 C12 C13 C14 0.0(3) . . . . ?
C11 C12 C13 C14 177.48(19) . . . . ?
C12 C13 C14 C15 -0.7(3) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C12 -0.4(3) . . . . ?
C13 C12 C17 C16 0.5(3) . . . . ?
C11 C12 C17 C16 -176.89(19) . . . . ?

_refine_diff_density_max         0.123
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.025

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1559466'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H18 O'
_chemical_formula_sum            'C29 H18 O'
_chemical_formula_weight         382.43

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                   6.635(5)
_cell_length_b                   15.315(5)
_cell_length_c                   19.049(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 98.654(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1913.6(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4864
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      27.65

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      1.327
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9844
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            15115
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.163
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             3361
_reflns_number_gt                2508
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0469P)²+0.3023P] 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         3361
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_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 0.3329(2) 0.06248(9) 0.85893(7) 0.0361(3) Uani 1 1 d . . . . .
C2 C 0.5333(2) 0.08282(10) 0.89399(8) 0.0442(4) Uani 1 1 d . . . . .
H2 H 0.5774 0.1405 0.8960 0.053 Uiso 1 1 calc R U . . .
C3 C 0.6602(2) 0.01942(11) 0.92432(9) 0.0532(4) Uani 1 1 d . . . . .
H3 H 0.7892 0.0345 0.9473 0.064 Uiso 1 1 calc R U . . .
C4 C 0.6000(3) -0.06903(12) 0.92164(9) 0.0591(5) Uani 1 1 d . . . . .
H4 H 0.6892 -0.1117 0.9425 0.071 Uiso 1 1 calc R U . . .
C5 C 0.4130(3) -0.09157(11) 0.88883(9) 0.0525(4) Uani 1 1 d . . . . .
H5 H 0.3749 -0.1501 0.8872 0.063 Uiso 1 1 calc R U . . .
C6 C 0.2724(2) -0.02763(10) 0.85661(7) 0.0408(4) Uani 1 1 d . . . . .
C7 C 0.0804(2) -0.05061(10) 0.82178(8) 0.0463(4) Uani 1 1 d . . . . .
H7 H 0.0395 -0.1086 0.8226 0.056 Uiso 1 1 calc R U . . .
C8 C -0.0527(2) 0.01014(10) 0.78568(7) 0.0405(4) Uani 1 1 d . . . . .
C9 C -0.2461(2) -0.01585(11) 0.74847(8) 0.0521(4) Uani 1 1 d . . . . .
H9 H -0.2832 -0.0744 0.7478 0.062 Uiso 1 1 calc R U . . .
C10 C -0.3760(3) 0.04324(12) 0.71428(9) 0.0573(5) Uani 1 1 d . . . . .
H10 H -0.5014 0.0253 0.6900 0.069 Uiso 1 1 calc R U . . .
C11 C -0.3214(2) 0.13210(12) 0.71544(8) 0.0538(4) Uani 1 1 d . . . . .
H11 H -0.4128 0.1727 0.6925 0.065 Uiso 1 1 calc R U . . .
C12 C -0.1382(2) 0.15953(10) 0.74931(8) 0.0444(4) Uani 1 1 d . . . . .
H12 H -0.1060 0.2186 0.7489 0.053 Uiso 1 1 calc R U . . .
C13 C 0.0068(2) 0.09978(9) 0.78561(7) 0.0356(3) Uani 1 1 d . . . . .
C14 C 0.1976(2) 0.12533(9) 0.82389(7) 0.0341(3) Uani 1 1 d . . . . .
C15 C 0.25530(19) 0.22015(9) 0.82370(7) 0.0350(3) Uani 1 1 d . . . . .
C16 C 0.32994(19) 0.26923(9) 0.89122(7) 0.0340(3) Uani 1 1 d . . . . .
C17 C 0.5047(2) 0.32315(9) 0.89303(7) 0.0367(3) Uani 1 1 d . . . . .
C18 C 0.6242(2) 0.32804(10) 0.83720(8) 0.0448(4) Uani 1 1 d . . . . .
H18 H 0.5853 0.2957 0.7961 0.054 Uiso 1 1 calc R U . . .
C19 C 0.7940(2) 0.37878(11) 0.84239(9) 0.0535(4) Uani 1 1 d . . . . .
H19 H 0.8700 0.3796 0.8052 0.064 Uiso 1 1 calc R U . . .
C20 C 0.8564(2) 0.42990(11) 0.90274(10) 0.0585(5) Uani 1 1 d . . . . .
H20 H 0.9705 0.4656 0.9048 0.070 Uiso 1 1 calc R U . . .
C21 C 0.7504(2) 0.42712(11) 0.95777(10) 0.0546(4) Uani 1 1 d . . . . .
H21 H 0.7930 0.4609 0.9979 0.066 Uiso 1 1 calc R U . . .
C22 C 0.5736(2) 0.37318(9) 0.95558(8) 0.0423(4) Uani 1 1 d . . . . .
C23 C 0.4684(2) 0.36787(10) 1.01301(8) 0.0482(4) Uani 1 1 d . . . . .
H23 H 0.5147 0.4003 1.0535 0.058 Uiso 1 1 calc R U . . .
C24 C 0.2961(2) 0.31596(10) 1.01235(7) 0.0413(4) Uani 1 1 d . . . . .
C25 C 0.1873(2) 0.31377(11) 1.07127(8) 0.0516(4) Uani 1 1 d . . . . .
H25 H 0.2352 0.3459 1.1118 0.062 Uiso 1 1 calc R U . . .
C26 C 0.0158(3) 0.26586(12) 1.06946(8) 0.0535(4) Uani 1 1 d . . . . .
H26 H -0.0530 0.2651 1.1085 0.064 Uiso 1 1 calc R U . . .
C27 C -0.0587(2) 0.21703(11) 1.00832(8) 0.0478(4) Uani 1 1 d . . . . .
H27 H -0.1776 0.1846 1.0073 0.057 Uiso 1 1 calc R U . . .
C28 C 0.0399(2) 0.21655(10) 0.95106(7) 0.0402(3) Uani 1 1 d . . . . .
H28 H -0.0129 0.1838 0.9114 0.048 Uiso 1 1 calc R U . . .
C29 C 0.22348(19) 0.26527(9) 0.95007(7) 0.0354(3) Uani 1 1 d . . . . .
O1 O 0.23984(16) 0.25867(7) 0.76706(5) 0.0509(3) 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
C1 C14 1.413(2) . ?
C1 C2 1.430(2) . ?
C1 C6 1.436(2) . ?
C2 C3 1.356(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.411(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.347(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.426(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.390(2) . ?
C7 C8 1.391(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.426(2) . ?
C8 C13 1.428(2) . ?
C9 C10 1.348(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.408(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.354(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.428(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.418(2) . ?
C14 C15 1.502(2) . ?
C15 O1 1.2203(16) . ?
C15 C16 1.5076(19) . ?
C16 C29 1.4134(19) . ?
C16 C17 1.420(2) . ?
C17 C18 1.421(2) . ?
C17 C22 1.432(2) . ?
C18 C19 1.360(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.401(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.348(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.430(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.386(2) . ?
C23 C24 1.391(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.423(2) . ?
C24 C29 1.4389(19) . ?
C25 C26 1.350(2) . ?
C25 H25 0.9300 . ?
C26 C27 1.410(2) . ?
C26 H26 0.9300 . ?
C27 C28 1.354(2) . ?
C27 H27 0.9300 . ?
C28 C29 1.431(2) . ?
C28 H28 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 C2 123.51(13) . . ?
C14 C1 C6 119.04(13) . . ?
C2 C1 C6 117.37(13) . . ?
C3 C2 C1 121.15(15) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 121.18(16) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 119.91(15) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 121.39(16) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 121.66(15) . . ?
C7 C6 C1 119.32(14) . . ?
C5 C6 C1 119.00(14) . . ?
C6 C7 C8 122.32(14) . . ?
C6 C7 H7 118.8 . . ?
C8 C7 H7 118.8 . . ?
C7 C8 C9 121.06(14) . . ?
C7 C8 C13 119.23(14) . . ?
C9 C8 C13 119.71(14) . . ?
C10 C9 C8 121.00(15) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 119.80(15) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 121.19(16) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 121.50(15) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 123.80(13) . . ?
C14 C13 C8 119.34(13) . . ?
C12 C13 C8 116.76(13) . . ?
C1 C14 C13 120.62(13) . . ?
C1 C14 C15 121.06(12) . . ?
C13 C14 C15 118.27(12) . . ?
O1 C15 C14 118.82(12) . . ?
O1 C15 C16 119.10(12) . . ?
C14 C15 C16 122.08(12) . . ?
C29 C16 C17 120.63(12) . . ?
C29 C16 C15 121.07(12) . . ?
C17 C16 C15 118.23(12) . . ?
C16 C17 C18 123.92(13) . . ?
C16 C17 C22 119.26(13) . . ?
C18 C17 C22 116.75(13) . . ?
C19 C18 C17 121.68(15) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 121.23(16) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 119.73(15) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 121.14(16) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C23 C22 C21 121.28(14) . . ?
C23 C22 C17 119.32(13) . . ?
C21 C22 C17 119.41(14) . . ?
C22 C23 C24 122.50(14) . . ?
C22 C23 H23 118.8 . . ?
C24 C23 H23 118.8 . . ?
C23 C24 C25 121.33(14) . . ?
C23 C24 C29 119.26(13) . . ?
C25 C24 C29 119.39(14) . . ?
C26 C25 C24 121.21(15) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C25 C26 C27 119.94(14) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C28 C27 C26 121.09(15) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C27 C28 C29 121.56(14) . . ?
C27 C28 H28 119.2 . . ?
C29 C28 H28 119.2 . . ?
C16 C29 C28 124.11(12) . . ?
C16 C29 C24 119.04(13) . . ?
C28 C29 C24 116.78(12) . . ?

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 -177.23(13) . . . . ?
C6 C1 C2 C3 -0.5(2) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C7 179.03(15) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C14 C1 C6 C7 -1.83(19) . . . . ?
C2 C1 C6 C7 -178.67(12) . . . . ?
C14 C1 C6 C5 176.78(12) . . . . ?
C2 C1 C6 C5 -0.06(19) . . . . ?
C5 C6 C7 C8 -175.21(13) . . . . ?
C1 C6 C7 C8 3.4(2) . . . . ?
C6 C7 C8 C9 177.94(13) . . . . ?
C6 C7 C8 C13 -1.6(2) . . . . ?
C7 C8 C9 C10 179.14(15) . . . . ?
C13 C8 C9 C10 -1.3(2) . . . . ?
C8 C9 C10 C11 -0.4(2) . . . . ?
C9 C10 C11 C12 1.3(3) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C11 C12 C13 C14 -177.78(13) . . . . ?
C11 C12 C13 C8 -1.3(2) . . . . ?
C7 C8 C13 C14 -1.69(19) . . . . ?
C9 C8 C13 C14 178.78(12) . . . . ?
C7 C8 C13 C12 -178.37(13) . . . . ?
C9 C8 C13 C12 2.10(19) . . . . ?
C2 C1 C14 C13 175.25(12) . . . . ?
C6 C1 C14 C13 -1.39(18) . . . . ?
C2 C1 C14 C15 -2.30(19) . . . . ?
C6 C1 C14 C15 -178.93(12) . . . . ?
C12 C13 C14 C1 179.57(12) . . . . ?
C8 C13 C14 C1 3.14(18) . . . . ?
C12 C13 C14 C15 -2.81(19) . . . . ?
C8 C13 C14 C15 -179.24(11) . . . . ?
C1 C14 C15 O1 127.92(14) . . . . ?
C13 C14 C15 O1 -49.69(18) . . . . ?
C1 C14 C15 C16 -52.57(17) . . . . ?
C13 C14 C15 C16 129.83(13) . . . . ?
O1 C15 C16 C29 130.44(14) . . . . ?
C14 C15 C16 C29 -49.08(18) . . . . ?
O1 C15 C16 C17 -46.49(18) . . . . ?
C14 C15 C16 C17 133.99(13) . . . . ?
C29 C16 C17 C18 177.47(13) . . . . ?
C15 C16 C17 C18 -5.6(2) . . . . ?
C29 C16 C17 C22 0.54(19) . . . . ?
C15 C16 C17 C22 177.48(12) . . . . ?
C16 C17 C18 C19 -178.00(14) . . . . ?
C22 C17 C18 C19 -1.0(2) . . . . ?
C17 C18 C19 C20 -1.2(2) . . . . ?
C18 C19 C20 C21 2.0(3) . . . . ?
C19 C20 C21 C22 -0.5(3) . . . . ?
C20 C21 C22 C23 177.76(15) . . . . ?
C20 C21 C22 C17 -1.8(2) . . . . ?
C16 C17 C22 C23 0.0(2) . . . . ?
C18 C17 C22 C23 -177.10(13) . . . . ?
C16 C17 C22 C21 179.58(13) . . . . ?
C18 C17 C22 C21 2.43(19) . . . . ?
C21 C22 C23 C24 -179.98(14) . . . . ?
C17 C22 C23 C24 -0.5(2) . . . . ?
C22 C23 C24 C25 -178.05(14) . . . . ?
C22 C23 C24 C29 0.3(2) . . . . ?
C23 C24 C25 C26 177.50(15) . . . . ?
C29 C24 C25 C26 -0.8(2) . . . . ?
C24 C25 C26 C27 -0.2(2) . . . . ?
C25 C26 C27 C28 0.6(2) . . . . ?
C26 C27 C28 C29 0.1(2) . . . . ?
C17 C16 C29 C28 176.33(13) . . . . ?
C15 C16 C29 C28 -0.5(2) . . . . ?
C17 C16 C29 C24 -0.72(19) . . . . ?
C15 C16 C29 C24 -177.57(12) . . . . ?
C27 C28 C29 C16 -178.18(14) . . . . ?
C27 C28 C29 C24 -1.1(2) . . . . ?
C23 C24 C29 C16 0.3(2) . . . . ?
C25 C24 C29 C16 178.68(13) . . . . ?
C23 C24 C29 C28 -176.95(13) . . . . ?
C25 C24 C29 C28 1.41(19) . . . . ?

_refine_diff_density_max         0.111
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.032

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1559465'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H16 O'
_chemical_formula_sum            'C25 H16 O'
_chemical_formula_weight         332.38

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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   25.998(3)
_cell_length_b                   8.5054(12)
_cell_length_c                   7.7480(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1713.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2298
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      24.52

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      1.289
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9848
_exptl_absorpt_correction_T_max  0.9885
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            7192
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.395
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.788
_diffrn_reflns_point_group_measured_fraction_full 0.798
_reflns_number_total             2652
_reflns_number_gt                2094
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.467
_reflns_Friedel_fraction_max     0.545
_reflns_Friedel_fraction_full    0.566

_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0398P)²+0.7184P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 638 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2652
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1271
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.47172(14) 0.2722(4) -0.1290(6) 0.0410(10) Uani 1 1 d . . . . .
C2 C 0.45102(16) 0.3420(5) -0.2812(6) 0.0515(11) Uani 1 1 d . . . . .
H2 H 0.4162 0.3667 -0.2858 0.062 Uiso 1 1 calc R U . . .
C3 C 0.48160(18) 0.3731(5) -0.4202(7) 0.0608(13) Uani 1 1 d . . . . .
H3 H 0.4673 0.4191 -0.5180 0.073 Uiso 1 1 calc R U . . .
C4 C 0.53415(18) 0.3372(6) -0.4183(8) 0.0651(14) Uani 1 1 d . . . . .
H4 H 0.5546 0.3613 -0.5131 0.078 Uiso 1 1 calc R U . . .
C5 C 0.55501(17) 0.2671(5) -0.2777(8) 0.0591(14) Uani 1 1 d . . . . .
H5 H 0.5898 0.2414 -0.2783 0.071 Uiso 1 1 calc R U . . .
C6 C 0.52505(15) 0.2320(5) -0.1295(7) 0.0464(11) Uani 1 1 d . . . . .
C7 C 0.54668(16) 0.1587(5) 0.0170(7) 0.0566(13) Uani 1 1 d . . . . .
H7 H 0.5816 0.1346 0.0171 0.068 Uiso 1 1 calc R U . . .
C8 C 0.51799(16) 0.1226(6) 0.1569(8) 0.0617(14) Uani 1 1 d . . . . .
H8 H 0.5329 0.0733 0.2517 0.074 Uiso 1 1 calc R U . . .
C9 C 0.46529(15) 0.1605(5) 0.1575(7) 0.0501(11) Uani 1 1 d . . . . .
H9 H 0.4456 0.1343 0.2535 0.060 Uiso 1 1 calc R U . . .
C10 C 0.44206(13) 0.2349(4) 0.0211(6) 0.0396(10) Uani 1 1 d . . . . .
C11 C 0.38685(14) 0.2804(4) 0.0406(6) 0.0386(9) Uani 1 1 d . . . . .
C12 C 0.35438(13) 0.1854(4) 0.1627(6) 0.0370(9) Uani 1 1 d . . . . .
C13 C 0.34051(12) 0.0306(4) 0.1169(6) 0.0369(9) Uani 1 1 d . . . . .
C14 C 0.35354(14) -0.0394(5) -0.0446(7) 0.0486(11) Uani 1 1 d . . . . .
H14 H 0.3721 0.0184 -0.1254 0.058 Uiso 1 1 calc R U . . .
C15 C 0.33922(16) -0.1894(5) -0.0823(7) 0.0573(14) Uani 1 1 d . . . . .
H15 H 0.3481 -0.2328 -0.1884 0.069 Uiso 1 1 calc R U . . .
C16 C 0.31104(16) -0.2799(5) 0.0378(8) 0.0577(14) Uani 1 1 d . . . . .
H16 H 0.3021 -0.3831 0.0114 0.069 Uiso 1 1 calc R U . . .
C17 C 0.29696(15) -0.2170(4) 0.1911(7) 0.0523(13) Uani 1 1 d . . . . .
H17 H 0.2776 -0.2771 0.2674 0.063 Uiso 1 1 calc R U . . .
C18 C 0.31110(13) -0.0611(4) 0.2387(6) 0.0399(10) Uani 1 1 d . . . . .
C19 C 0.29623(14) 0.0058(5) 0.3943(6) 0.0450(10) Uani 1 1 d . . . . .
H19 H 0.2780 -0.0550 0.4731 0.054 Uiso 1 1 calc R U . . .
C20 C 0.30770(13) 0.1610(5) 0.4360(6) 0.0394(9) Uani 1 1 d . . . . .
C21 C 0.28999(15) 0.2333(6) 0.5912(6) 0.0524(11) Uani 1 1 d . . . . .
H21 H 0.2709 0.1740 0.6690 0.063 Uiso 1 1 calc R U . . .
C22 C 0.30010(17) 0.3841(6) 0.6280(7) 0.0599(13) Uani 1 1 d . . . . .
H22 H 0.2878 0.4284 0.7297 0.072 Uiso 1 1 calc R U . . .
C23 C 0.32968(17) 0.4761(6) 0.5113(7) 0.0604(13) Uani 1 1 d . . . . .
H23 H 0.3364 0.5809 0.5370 0.073 Uiso 1 1 calc R U . . .
C24 C 0.34823(16) 0.4130(5) 0.3632(6) 0.0469(11) Uani 1 1 d . . . . .
H24 H 0.3684 0.4744 0.2906 0.056 Uiso 1 1 calc R U . . .
C25 C 0.33725(13) 0.2538(4) 0.3164(6) 0.0354(9) Uani 1 1 d . . . . .
O1 O 0.36839(10) 0.3932(3) -0.0351(5) 0.0538(8) 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
C1 C2 1.426(6) . ?
C1 C6 1.428(5) . ?
C1 C10 1.431(6) . ?
C2 C3 1.365(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.400(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.355(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.419(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.412(7) . ?
C7 C8 1.352(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.407(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.494(5) . ?
C11 O1 1.222(4) . ?
C11 C12 1.503(6) . ?
C12 C25 1.398(6) . ?
C12 C13 1.411(5) . ?
C13 C14 1.427(6) . ?
C13 C18 1.443(6) . ?
C14 C15 1.361(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.413(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.354(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.425(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.388(6) . ?
C19 C20 1.391(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.427(6) . ?
C20 C25 1.440(6) . ?
C21 C22 1.340(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.422(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.356(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.431(5) . ?
C24 H24 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 117.6(4) . . ?
C2 C1 C10 124.1(3) . . ?
C6 C1 C10 118.2(4) . . ?
C3 C2 C1 120.9(4) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 121.2(5) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 119.7(5) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.6(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 121.6(4) . . ?
C7 C6 C1 119.4(4) . . ?
C5 C6 C1 119.0(4) . . ?
C8 C7 C6 121.7(4) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 119.2(5) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 122.1(4) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C9 C10 C1 119.4(3) . . ?
C9 C10 C11 117.7(4) . . ?
C1 C10 C11 122.8(4) . . ?
O1 C11 C10 122.2(4) . . ?
O1 C11 C12 120.2(3) . . ?
C10 C11 C12 117.6(3) . . ?
C25 C12 C13 121.4(4) . . ?
C25 C12 C11 119.4(3) . . ?
C13 C12 C11 119.1(4) . . ?
C12 C13 C14 123.3(4) . . ?
C12 C13 C18 118.4(4) . . ?
C14 C13 C18 118.3(3) . . ?
C15 C14 C13 121.0(4) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 120.8(5) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 120.2(4) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 121.7(4) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C19 C18 C17 122.3(4) . . ?
C19 C18 C13 119.6(3) . . ?
C17 C18 C13 118.1(4) . . ?
C18 C19 C20 122.1(4) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 H19 119.0 . . ?
C19 C20 C21 122.4(4) . . ?
C19 C20 C25 119.0(4) . . ?
C21 C20 C25 118.6(4) . . ?
C22 C21 C20 121.9(4) . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C21 C22 C23 119.8(5) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C24 C23 C22 120.9(4) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 121.2(4) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C12 C25 C24 123.1(4) . . ?
C12 C25 C20 119.3(3) . . ?
C24 C25 C20 117.5(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 -1.9(6) . . . . ?
C10 C1 C2 C3 -179.4(4) . . . . ?
C1 C2 C3 C4 0.2(7) . . . . ?
C2 C3 C4 C5 1.5(7) . . . . ?
C3 C4 C5 C6 -1.4(7) . . . . ?
C4 C5 C6 C7 179.8(4) . . . . ?
C4 C5 C6 C1 -0.2(6) . . . . ?
C2 C1 C6 C7 -178.2(4) . . . . ?
C10 C1 C6 C7 -0.5(5) . . . . ?
C2 C1 C6 C5 1.8(5) . . . . ?
C10 C1 C6 C5 179.6(4) . . . . ?
C5 C6 C7 C8 -178.8(4) . . . . ?
C1 C6 C7 C8 1.3(7) . . . . ?
C6 C7 C8 C9 -0.7(7) . . . . ?
C7 C8 C9 C10 -0.8(7) . . . . ?
C8 C9 C10 C1 1.5(6) . . . . ?
C8 C9 C10 C11 -175.5(4) . . . . ?
C2 C1 C10 C9 176.7(4) . . . . ?
C6 C1 C10 C9 -0.8(5) . . . . ?
C2 C1 C10 C11 -6.4(6) . . . . ?
C6 C1 C10 C11 176.0(3) . . . . ?
C9 C10 C11 O1 151.2(4) . . . . ?
C1 C10 C11 O1 -25.7(6) . . . . ?
C9 C10 C11 C12 -26.7(5) . . . . ?
C1 C10 C11 C12 156.3(4) . . . . ?
O1 C11 C12 C25 -67.3(5) . . . . ?
C10 C11 C12 C25 110.7(4) . . . . ?
O1 C11 C12 C13 110.7(4) . . . . ?
C10 C11 C12 C13 -71.4(5) . . . . ?
C25 C12 C13 C14 174.7(3) . . . . ?
C11 C12 C13 C14 -3.3(5) . . . . ?
C25 C12 C13 C18 -4.5(5) . . . . ?
C11 C12 C13 C18 177.5(3) . . . . ?
C12 C13 C14 C15 180.0(4) . . . . ?
C18 C13 C14 C15 -0.8(5) . . . . ?
C13 C14 C15 C16 0.0(6) . . . . ?
C14 C15 C16 C17 1.4(7) . . . . ?
C15 C16 C17 C18 -1.9(6) . . . . ?
C16 C17 C18 C19 178.9(4) . . . . ?
C16 C17 C18 C13 1.0(6) . . . . ?
C12 C13 C18 C19 1.6(5) . . . . ?
C14 C13 C18 C19 -177.6(3) . . . . ?
C12 C13 C18 C17 179.6(3) . . . . ?
C14 C13 C18 C17 0.4(5) . . . . ?
C17 C18 C19 C20 -176.4(3) . . . . ?
C13 C18 C19 C20 1.6(5) . . . . ?
C18 C19 C20 C21 176.3(4) . . . . ?
C18 C19 C20 C25 -1.9(5) . . . . ?
C19 C20 C21 C22 -178.2(4) . . . . ?
C25 C20 C21 C22 0.0(6) . . . . ?
C20 C21 C22 C23 -0.6(7) . . . . ?
C21 C22 C23 C24 -0.5(7) . . . . ?
C22 C23 C24 C25 2.1(7) . . . . ?
C13 C12 C25 C24 -176.6(3) . . . . ?
C11 C12 C25 C24 1.3(5) . . . . ?
C13 C12 C25 C20 4.2(5) . . . . ?
C11 C12 C25 C20 -177.8(3) . . . . ?
C23 C24 C25 C12 178.2(4) . . . . ?
C23 C24 C25 C20 -2.7(6) . . . . ?
C19 C20 C25 C12 -1.0(5) . . . . ?
C21 C20 C25 C12 -179.2(3) . . . . ?
C19 C20 C25 C24 179.8(3) . . . . ?
C21 C20 C25 C24 1.6(5) . . . . ?

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.041

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1559463'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H14 O'
_chemical_formula_sum            'C21 H14 O'
_chemical_formula_weight         282.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   14.081(5)
_cell_length_b                   7.291(5)
_cell_length_c                   15.214(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 106.982(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1493.8(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3299
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      26.24

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      1.255
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9850
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            11519
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.800
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2921
_reflns_number_gt                2055
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0834P)²+0.5940P] 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         2921
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.1753
_refine_ls_wR_factor_gt          0.1517
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.30921(17) 0.0029(4) 0.66275(17) 0.0657(6) Uani 1 1 d . . . . .
H1 H 0.2674 -0.0039 0.6029 0.079 Uiso 1 1 calc R U . . .
C2 C 0.31169(18) -0.1378(4) 0.72172(18) 0.0697(7) Uani 1 1 d . . . . .
H2 H 0.2720 -0.2407 0.7025 0.084 Uiso 1 1 calc R U . . .
C3 C 0.37468(18) -0.1265(3) 0.81179(18) 0.0669(6) Uani 1 1 d . . . . .
H3 H 0.3758 -0.2226 0.8522 0.080 Uiso 1 1 calc R U . . .
C4 C 0.43404(16) 0.0208(3) 0.84159(16) 0.0575(6) Uani 1 1 d . . . . .
H4 H 0.4753 0.0236 0.9017 0.069 Uiso 1 1 calc R U . . .
C5 C 0.43394(13) 0.1716(3) 0.78182(14) 0.0467(5) Uani 1 1 d . . . . .
C6 C 0.36912(14) 0.1592(3) 0.69094(14) 0.0513(5) Uani 1 1 d . . . . .
C7 C 0.36453(18) 0.3077(3) 0.62883(16) 0.0654(6) Uani 1 1 d . . . . .
H7 H 0.3220 0.2998 0.5693 0.079 Uiso 1 1 calc R U . . .
C8 C 0.42038(18) 0.4587(4) 0.65441(16) 0.0686(7) Uani 1 1 d . . . . .
H8 H 0.4159 0.5550 0.6133 0.082 Uiso 1 1 calc R U . . .
C9 C 0.48582(16) 0.4701(3) 0.74414(15) 0.0574(6) Uani 1 1 d . . . . .
H9 H 0.5249 0.5744 0.7610 0.069 Uiso 1 1 calc R U . . .
C10 C 0.49401(14) 0.3328(3) 0.80755(13) 0.0473(5) Uani 1 1 d . . . . .
C11 C 0.56598(15) 0.3595(3) 0.90026(14) 0.0541(5) Uani 1 1 d . . . . .
C12 C 0.64366(15) 0.5078(3) 0.91111(14) 0.0519(5) Uani 1 1 d . . . . .
C13 C 0.63239(18) 0.6745(3) 0.94747(17) 0.0643(6) Uani 1 1 d . . . . .
H13 H 0.5755 0.6981 0.9649 0.077 Uiso 1 1 calc R U . . .
C14 C 0.7058(2) 0.8121(3) 0.95907(18) 0.0723(7) Uani 1 1 d . . . . .
H14 H 0.6960 0.9265 0.9820 0.087 Uiso 1 1 calc R U . . .
C15 C 0.7895(2) 0.7778(4) 0.93712(18) 0.0724(7) Uani 1 1 d . . . . .
H15 H 0.8376 0.8689 0.9456 0.087 Uiso 1 1 calc R U . . .
C16 C 0.80660(16) 0.6038(3) 0.90096(16) 0.0614(6) Uani 1 1 d . . . . .
C17 C 0.73099(15) 0.4700(3) 0.88770(13) 0.0508(5) Uani 1 1 d . . . . .
C18 C 0.74831(19) 0.2953(4) 0.85059(17) 0.0679(7) Uani 1 1 d . . . . .
H18 H 0.7005 0.2036 0.8411 0.082 Uiso 1 1 calc R U . . .
C19 C 0.8336(2) 0.2645(4) 0.8297(2) 0.0877(9) Uani 1 1 d . . . . .
H19 H 0.8434 0.1515 0.8053 0.105 Uiso 1 1 calc R U . . .
C20 C 0.9073(2) 0.3976(5) 0.8437(3) 0.0999(10) Uani 1 1 d . . . . .
H20 H 0.9657 0.3724 0.8292 0.120 Uiso 1 1 calc R U . . .
C21 C 0.8943(2) 0.5641(5) 0.8785(2) 0.0874(9) Uani 1 1 d . . . . .
H21 H 0.9439 0.6525 0.8875 0.105 Uiso 1 1 calc R U . . .
O1 O 0.56526(15) 0.2740(3) 0.96766(11) 0.0892(7) 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
C1 C2 1.357(3) . ?
C1 C6 1.408(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.401(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.355(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.426(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.420(3) . ?
C5 C10 1.434(3) . ?
C6 C7 1.426(3) . ?
C7 C8 1.343(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.409(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.490(3) . ?
C11 O1 1.203(3) . ?
C11 C12 1.512(3) . ?
C12 C13 1.364(3) . ?
C12 C17 1.404(3) . ?
C13 C14 1.414(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.339(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.431(4) . ?
C15 H15 0.9300 . ?
C16 C21 1.405(4) . ?
C16 C17 1.414(3) . ?
C17 C18 1.443(3) . ?
C18 C19 1.348(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.391(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.358(4) . ?
C20 H20 0.9300 . ?
C21 H21 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 120.9(2) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C1 C2 C3 119.3(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 121.8(2) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 116.91(19) . . ?
C6 C5 C10 118.55(18) . . ?
C4 C5 C10 124.54(18) . . ?
C1 C6 C5 120.4(2) . . ?
C1 C6 C7 120.4(2) . . ?
C5 C6 C7 119.3(2) . . ?
C8 C7 C6 121.4(2) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 119.4(2) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 122.4(2) . . ?
C10 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
C9 C10 C5 118.98(19) . . ?
C9 C10 C11 117.69(19) . . ?
C5 C10 C11 123.33(18) . . ?
O1 C11 C10 124.5(2) . . ?
O1 C11 C12 117.61(19) . . ?
C10 C11 C12 117.86(18) . . ?
C13 C12 C17 119.5(2) . . ?
C13 C12 C11 121.0(2) . . ?
C17 C12 C11 119.4(2) . . ?
C12 C13 C14 121.0(2) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 121.4(2) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C21 C16 C17 120.2(2) . . ?
C21 C16 C15 122.3(2) . . ?
C17 C16 C15 117.5(2) . . ?
C12 C17 C16 120.5(2) . . ?
C12 C17 C18 122.2(2) . . ?
C16 C17 C18 117.3(2) . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 121.6(3) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C21 C20 C19 120.3(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C16 120.4(3) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?

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 0.1(4) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C3 C4 C5 C10 179.8(2) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C2 C1 C6 C7 -178.9(2) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C10 C5 C6 C1 179.71(19) . . . . ?
C4 C5 C6 C7 178.74(19) . . . . ?
C10 C5 C6 C7 -1.0(3) . . . . ?
C1 C6 C7 C8 179.5(2) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C6 C7 C8 C9 0.8(4) . . . . ?
C7 C8 C9 C10 -0.9(4) . . . . ?
C8 C9 C10 C5 0.0(3) . . . . ?
C8 C9 C10 C11 179.8(2) . . . . ?
C6 C5 C10 C9 0.9(3) . . . . ?
C4 C5 C10 C9 -178.81(19) . . . . ?
C6 C5 C10 C11 -178.84(18) . . . . ?
C4 C5 C10 C11 1.4(3) . . . . ?
C9 C10 C11 O1 162.3(2) . . . . ?
C5 C10 C11 O1 -18.0(4) . . . . ?
C9 C10 C11 C12 -16.0(3) . . . . ?
C5 C10 C11 C12 163.71(19) . . . . ?
O1 C11 C12 C13 -78.3(3) . . . . ?
C10 C11 C12 C13 100.1(2) . . . . ?
O1 C11 C12 C17 98.4(3) . . . . ?
C10 C11 C12 C17 -83.2(2) . . . . ?
C17 C12 C13 C14 2.1(3) . . . . ?
C11 C12 C13 C14 178.9(2) . . . . ?
C12 C13 C14 C15 -2.2(4) . . . . ?
C13 C14 C15 C16 0.6(4) . . . . ?
C14 C15 C16 C21 -179.2(3) . . . . ?
C14 C15 C16 C17 1.1(4) . . . . ?
C13 C12 C17 C16 -0.4(3) . . . . ?
C11 C12 C17 C16 -177.26(19) . . . . ?
C13 C12 C17 C18 178.8(2) . . . . ?
C11 C12 C17 C18 2.0(3) . . . . ?
C21 C16 C17 C12 179.2(2) . . . . ?
C15 C16 C17 C12 -1.1(3) . . . . ?
C21 C16 C17 C18 -0.1(3) . . . . ?
C15 C16 C17 C18 179.6(2) . . . . ?
C12 C17 C18 C19 -179.5(2) . . . . ?
C16 C17 C18 C19 -0.2(4) . . . . ?
C17 C18 C19 C20 0.6(5) . . . . ?
C18 C19 C20 C21 -0.6(6) . . . . ?
C19 C20 C21 C16 0.2(5) . . . . ?
C17 C16 C21 C20 0.1(4) . . . . ?
C15 C16 C21 C20 -179.5(3) . . . . ?

_refine_diff_density_max         0.373
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.038

_shelxl_version_number           2014-3

