# 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_0378_290114_mh_monobnzylpyr_0m
_database_code_depnum_ccdc_archive 'CCDC 1440151'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-04-27 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_0360_201113_mh_bzy_pyr1_0m
_database_code_depnum_ccdc_archive 'CCDC 1440152'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '1,3 Dibenzoylpyrene'
_chemical_name_common            pyrene-1,3-diylbis(phenylmethanone)
_chemical_melting_point          437.15
_chemical_formula_moiety         'C30 H18 O2'
_chemical_formula_sum            'C30 H18 O2'
_chemical_formula_weight         410.44

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                   10.0326(3)
_cell_length_b                   10.6238(3)
_cell_length_c                   11.6287(4)
_cell_angle_alpha                94.4890(10)
_cell_angle_beta                 99.490(2)
_cell_angle_gamma                117.2630(10)
_cell_volume                     1069.82(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8664
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      28.27

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      1.273
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_T_max  0.9844
_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            15706
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3761
_reflns_number_gt                3092
_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)+(0.0708P)²+0.1601P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3761
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1292
_refine_ls_wR_factor_gt          0.1147
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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 0.20122(16) 0.49423(14) 0.11997(12) 0.0463(3) Uani 1 1 d . . .
H1 H 0.1324 0.4124 0.0644 0.056 Uiso 1 1 calc R . .
C2 C 0.27130(16) 0.62556(14) 0.08216(11) 0.0447(3) Uani 1 1 d . . .
C3 C 0.38214(16) 0.74937(14) 0.16456(12) 0.0442(3) Uani 1 1 d . . .
C4 C 0.46806(18) 0.88586(16) 0.13064(14) 0.0567(4) Uani 1 1 d . . .
H4 H 0.4455 0.8963 0.0523 0.068 Uiso 1 1 calc R . .
C5 C 0.58075(19) 0.99928(17) 0.20994(15) 0.0634(4) Uani 1 1 d . . .
H5 H 0.6356 1.0854 0.1843 0.076 Uiso 1 1 calc R . .
C6 C 0.61858(17) 0.99149(16) 0.33190(14) 0.0567(4) Uani 1 1 d . . .
C7 C 0.7334(2) 1.10849(19) 0.41585(18) 0.0738(5) Uani 1 1 d . . .
H7 H 0.7895 1.1958 0.3923 0.089 Uiso 1 1 calc R . .
C8 C 0.7645(2) 1.0962(2) 0.53303(19) 0.0823(6) Uani 1 1 d . . .
H8 H 0.8405 1.1756 0.5878 0.099 Uiso 1 1 calc R . .
C9 C 0.6846(2) 0.9680(2) 0.56987(16) 0.0732(5) Uani 1 1 d . . .
H9 H 0.7068 0.9617 0.6494 0.088 Uiso 1 1 calc R . .
C10 C 0.57089(17) 0.84751(17) 0.48974(13) 0.0563(4) Uani 1 1 d . . .
C11 C 0.4885(2) 0.71141(18) 0.52437(13) 0.0634(4) Uani 1 1 d . . .
H11 H 0.5105 0.7030 0.6034 0.076 Uiso 1 1 calc R . .
C12 C 0.38025(19) 0.59543(17) 0.44609(13) 0.0571(4) Uani 1 1 d . . .
H12 H 0.3306 0.5083 0.4719 0.069 Uiso 1 1 calc R . .
C13 C 0.33931(16) 0.60256(14) 0.32345(11) 0.0445(3) Uani 1 1 d . . .
C14 C 0.23084(16) 0.48144(14) 0.23846(11) 0.0449(3) Uani 1 1 d . . .
C15 C 0.41797(15) 0.73675(14) 0.28530(11) 0.0427(3) Uani 1 1 d . . .
C16 C 0.53533(16) 0.85844(15) 0.36894(12) 0.0479(3) Uani 1 1 d . . .
C17 C 0.14394(16) 0.33762(14) 0.27308(12) 0.0474(3) Uani 1 1 d . . .
C18 C 0.22503(16) 0.63220(15) -0.04551(12) 0.0482(3) Uani 1 1 d . . .
C19 C 0.22714(15) 0.52936(14) -0.13857(11) 0.0463(3) Uani 1 1 d . . .
C20 C 0.31136(18) 0.45741(18) -0.11491(13) 0.0588(4) Uani 1 1 d . . .
H20 H 0.3643 0.4689 -0.0379 0.071 Uiso 1 1 calc R . .
C21 C 0.3170(2) 0.3687(2) -0.20517(17) 0.0794(5) Uani 1 1 d . . .
H21 H 0.3738 0.3208 -0.1889 0.095 Uiso 1 1 calc R . .
C22 C 0.2390(2) 0.3512(2) -0.31887(17) 0.0799(5) Uani 1 1 d . . .
H22 H 0.2439 0.2921 -0.3796 0.096 Uiso 1 1 calc R . .
C23 C 0.1543(2) 0.4200(2) -0.34338(14) 0.0709(5) Uani 1 1 d . . .
H23 H 0.1001 0.4061 -0.4204 0.085 Uiso 1 1 calc R . .
C24 C 0.14847(18) 0.51016(17) -0.25461(13) 0.0578(4) Uani 1 1 d . . .
H24 H 0.0920 0.5582 -0.2722 0.069 Uiso 1 1 calc R . .
C25 C 0.14399(16) 0.21077(14) 0.20874(12) 0.0486(3) Uani 1 1 d . . .
C26 C 0.03054(19) 0.07374(16) 0.21182(15) 0.0629(4) Uani 1 1 d . . .
H26 H -0.0469 0.0618 0.2511 0.075 Uiso 1 1 calc R . .
C27 C 0.0325(2) -0.04519(18) 0.15647(18) 0.0790(6) Uani 1 1 d . . .
H27 H -0.0444 -0.1370 0.1580 0.095 Uiso 1 1 calc R . .
C28 C 0.1465(3) -0.0290(2) 0.09963(17) 0.0825(6) Uani 1 1 d . . .
H28 H 0.1470 -0.1097 0.0629 0.099 Uiso 1 1 calc R . .
C29 C 0.2599(3) 0.1054(2) 0.09654(16) 0.0773(5) Uani 1 1 d . . .
H29 H 0.3375 0.1159 0.0579 0.093 Uiso 1 1 calc R . .
C30 C 0.2596(2) 0.22596(18) 0.15079(14) 0.0602(4) Uani 1 1 d . . .
H30 H 0.3369 0.3172 0.1484 0.072 Uiso 1 1 calc R . .
O1 O 0.07506(13) 0.32509(11) 0.35195(9) 0.0645(3) Uani 1 1 d . . .
O2 O 0.18662(15) 0.72136(12) -0.07309(9) 0.0713(4) 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 1.3905(18) . ?
C1 C14 1.3916(18) . ?
C1 H1 0.9300 . ?
C2 C3 1.4129(19) . ?
C2 C18 1.4980(18) . ?
C3 C15 1.4233(18) . ?
C3 C4 1.4344(19) . ?
C4 C5 1.347(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.425(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.397(2) . ?
C6 C16 1.419(2) . ?
C7 C8 1.377(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.373(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.390(2) . ?
C9 H9 0.9300 . ?
C10 C16 1.419(2) . ?
C10 C11 1.429(2) . ?
C11 C12 1.341(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.4354(19) . ?
C12 H12 0.9300 . ?
C13 C14 1.4072(19) . ?
C13 C15 1.4268(18) . ?
C14 C17 1.4994(18) . ?
C15 C16 1.426(2) . ?
C17 O1 1.2166(16) . ?
C17 C25 1.4895(19) . ?
C18 O2 1.2205(16) . ?
C18 C19 1.4862(19) . ?
C19 C20 1.386(2) . ?
C19 C24 1.394(2) . ?
C20 C21 1.381(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.372(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.364(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.379(2) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.386(2) . ?
C25 C30 1.389(2) . ?
C26 C27 1.382(2) . ?
C26 H26 0.9300 . ?
C27 C28 1.364(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.367(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.384(2) . ?
C29 H29 0.9300 . ?
C30 H30 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 C14 122.02(13) . . ?
C2 C1 H1 119.0 . . ?
C14 C1 H1 119.0 . . ?
C1 C2 C3 119.64(12) . . ?
C1 C2 C18 118.75(12) . . ?
C3 C2 C18 121.60(12) . . ?
C2 C3 C15 118.89(12) . . ?
C2 C3 C4 122.80(12) . . ?
C15 C3 C4 118.17(13) . . ?
C5 C4 C3 121.38(14) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 122.11(14) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C7 C6 C16 118.91(15) . . ?
C7 C6 C5 122.98(15) . . ?
C16 C6 C5 118.11(13) . . ?
C8 C7 C6 120.86(16) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C9 C8 C7 120.72(16) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.81(17) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C16 119.38(15) . . ?
C9 C10 C11 122.31(15) . . ?
C16 C10 C11 118.31(13) . . ?
C12 C11 C10 121.83(14) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 121.56(14) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C15 118.71(12) . . ?
C14 C13 C12 122.79(12) . . ?
C15 C13 C12 118.42(13) . . ?
C1 C14 C13 119.99(12) . . ?
C1 C14 C17 118.77(12) . . ?
C13 C14 C17 121.23(11) . . ?
C3 C15 C16 119.92(12) . . ?
C3 C15 C13 120.62(12) . . ?
C16 C15 C13 119.44(12) . . ?
C10 C16 C6 119.30(14) . . ?
C10 C16 C15 120.42(13) . . ?
C6 C16 C15 120.28(13) . . ?
O1 C17 C25 120.87(12) . . ?
O1 C17 C14 120.65(12) . . ?
C25 C17 C14 118.48(11) . . ?
O2 C18 C19 120.22(12) . . ?
O2 C18 C2 120.53(12) . . ?
C19 C18 C2 119.26(11) . . ?
C20 C19 C24 118.84(13) . . ?
C20 C19 C18 122.08(12) . . ?
C24 C19 C18 119.00(12) . . ?
C21 C20 C19 120.28(15) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C20 120.07(17) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 120.35(16) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 120.40(16) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C19 120.04(15) . . ?
C23 C24 H24 120.0 . . ?
C19 C24 H24 120.0 . . ?
C26 C25 C30 118.97(14) . . ?
C26 C25 C17 119.31(13) . . ?
C30 C25 C17 121.63(13) . . ?
C27 C26 C25 119.99(17) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C28 C27 C26 120.54(18) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C28 C29 120.21(17) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C28 C29 C30 120.19(18) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C29 C30 C25 120.10(16) . . ?
C29 C30 H30 120.0 . . ?
C25 C30 H30 120.0 . . ?

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 3.3(2) . . . . ?
C14 C1 C2 C18 -175.75(12) . . . . ?
C1 C2 C3 C15 -0.83(19) . . . . ?
C18 C2 C3 C15 178.25(11) . . . . ?
C1 C2 C3 C4 174.89(12) . . . . ?
C18 C2 C3 C4 -6.0(2) . . . . ?
C2 C3 C4 C5 -175.15(14) . . . . ?
C15 C3 C4 C5 0.6(2) . . . . ?
C3 C4 C5 C6 -1.5(3) . . . . ?
C4 C5 C6 C7 -178.98(16) . . . . ?
C4 C5 C6 C16 1.0(2) . . . . ?
C16 C6 C7 C8 -0.8(3) . . . . ?
C5 C6 C7 C8 179.19(17) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 C16 -1.2(3) . . . . ?
C8 C9 C10 C11 178.23(17) . . . . ?
C9 C10 C11 C12 -179.19(16) . . . . ?
C16 C10 C11 C12 0.3(2) . . . . ?
C10 C11 C12 C13 -1.2(3) . . . . ?
C11 C12 C13 C14 177.31(15) . . . . ?
C11 C12 C13 C15 0.7(2) . . . . ?
C2 C1 C14 C13 -2.7(2) . . . . ?
C2 C1 C14 C17 176.57(12) . . . . ?
C15 C13 C14 C1 -0.51(19) . . . . ?
C12 C13 C14 C1 -177.13(13) . . . . ?
C15 C13 C14 C17 -179.72(11) . . . . ?
C12 C13 C14 C17 3.7(2) . . . . ?
C2 C3 C15 C16 176.64(11) . . . . ?
C4 C3 C15 C16 0.72(19) . . . . ?
C2 C3 C15 C13 -2.29(19) . . . . ?
C4 C3 C15 C13 -178.21(12) . . . . ?
C14 C13 C15 C3 2.95(19) . . . . ?
C12 C13 C15 C3 179.73(12) . . . . ?
C14 C13 C15 C16 -175.98(12) . . . . ?
C12 C13 C15 C16 0.79(19) . . . . ?
C9 C10 C16 C6 1.2(2) . . . . ?
C11 C10 C16 C6 -178.30(13) . . . . ?
C9 C10 C16 C15 -179.32(14) . . . . ?
C11 C10 C16 C15 1.2(2) . . . . ?
C7 C6 C16 C10 -0.2(2) . . . . ?
C5 C6 C16 C10 179.81(13) . . . . ?
C7 C6 C16 C15 -179.67(14) . . . . ?
C5 C6 C16 C15 0.3(2) . . . . ?
C3 C15 C16 C10 179.34(12) . . . . ?
C13 C15 C16 C10 -1.7(2) . . . . ?
C3 C15 C16 C6 -1.2(2) . . . . ?
C13 C15 C16 C6 177.78(12) . . . . ?
C1 C14 C17 O1 -127.22(15) . . . . ?
C13 C14 C17 O1 52.0(2) . . . . ?
C1 C14 C17 C25 52.79(18) . . . . ?
C13 C14 C17 C25 -127.99(14) . . . . ?
C1 C2 C18 O2 128.34(15) . . . . ?
C3 C2 C18 O2 -50.7(2) . . . . ?
C1 C2 C18 C19 -51.98(18) . . . . ?
C3 C2 C18 C19 128.93(14) . . . . ?
O2 C18 C19 C20 160.05(15) . . . . ?
C2 C18 C19 C20 -19.6(2) . . . . ?
O2 C18 C19 C24 -16.6(2) . . . . ?
C2 C18 C19 C24 163.76(13) . . . . ?
C24 C19 C20 C21 0.2(2) . . . . ?
C18 C19 C20 C21 -176.46(15) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C20 C21 C22 C23 -0.6(3) . . . . ?
C21 C22 C23 C24 1.3(3) . . . . ?
C22 C23 C24 C19 -1.2(3) . . . . ?
C20 C19 C24 C23 0.5(2) . . . . ?
C18 C19 C24 C23 177.21(14) . . . . ?
O1 C17 C25 C26 19.7(2) . . . . ?
C14 C17 C25 C26 -160.28(13) . . . . ?
O1 C17 C25 C30 -156.84(15) . . . . ?
C14 C17 C25 C30 23.15(19) . . . . ?
C30 C25 C26 C27 -0.8(2) . . . . ?
C17 C25 C26 C27 -177.45(14) . . . . ?
C25 C26 C27 C28 0.7(3) . . . . ?
C26 C27 C28 C29 -0.2(3) . . . . ?
C27 C28 C29 C30 -0.2(3) . . . . ?
C28 C29 C30 C25 0.1(3) . . . . ?
C26 C25 C30 C29 0.4(2) . . . . ?
C17 C25 C30 C29 176.99(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.037
_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_new
_database_code_depnum_ccdc_archive 'CCDC 1440153'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        pyrene-1,6-diylbis(phenylmethanone)
_chemical_name_common            '1,6 Dibenzoylpyrene'
_chemical_melting_point          506.15
_chemical_formula_moiety         'C30 H18 O2'
_chemical_formula_sum            'C30 H18 O2'
_chemical_formula_weight         410.44

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '
_symmetry_space_group_name_Hall  '-P 2yn  '

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

_cell_length_a                   5.4689(3)
_cell_length_b                   8.2510(5)
_cell_length_c                   22.5720(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.604(2)
_cell_angle_gamma                90.00
_cell_volume                     1013.67(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3667
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      28.39

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      1.344
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9836
_exptl_absorpt_correction_T_max  0.9876
_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         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7234
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         24.70
_reflns_number_total             1732
_reflns_number_gt                1443
_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)+(0.0452P)²+0.2526P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1732
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0955
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.6914(3) 0.84570(17) 0.09250(6) 0.0389(3) Uani 1 1 d . . .
C2 C 0.5608(3) 0.98665(17) 0.10287(6) 0.0428(4) Uani 1 1 d . . .
H2 H 0.4455 0.9844 0.1305 0.051 Uiso 1 1 calc R . .
C3 C 0.5984(3) 1.12881(17) 0.07320(6) 0.0422(4) Uani 1 1 d . . .
H3 H 0.5062 1.2201 0.0805 0.051 Uiso 1 1 calc R . .
C4 C 1.1834(3) 0.71740(17) -0.00095(6) 0.0420(4) Uani 1 1 d . . .
H4 H 1.2742 0.6252 -0.0079 0.050 Uiso 1 1 calc R . .
C5 C 1.0150(3) 0.70993(17) 0.03837(6) 0.0417(4) Uani 1 1 d . . .
H5 H 0.9920 0.6126 0.0579 0.050 Uiso 1 1 calc R . .
C6 C 0.8690(2) 0.84829(16) 0.05122(6) 0.0355(3) Uani 1 1 d . . .
C7 C 0.9113(2) 0.99599(16) 0.02112(6) 0.0347(3) Uani 1 1 d . . .
C8 C 0.7730(3) 1.13718(16) 0.03248(6) 0.0374(3) Uani 1 1 d . . .
C9 C 0.6210(3) 0.69429(17) 0.12274(6) 0.0414(4) Uani 1 1 d . . .
C10 C 0.5548(3) 0.70607(17) 0.18528(6) 0.0404(4) Uani 1 1 d . . .
C11 C 0.3599(3) 0.6152(2) 0.20215(7) 0.0514(4) Uani 1 1 d . . .
H11 H 0.2673 0.5521 0.1741 0.062 Uiso 1 1 calc R . .
C12 C 0.3030(3) 0.6178(2) 0.26016(7) 0.0588(5) Uani 1 1 d . . .
H12 H 0.1687 0.5594 0.2709 0.071 Uiso 1 1 calc R . .
C13 C 0.4437(3) 0.7065(2) 0.30231(7) 0.0573(5) Uani 1 1 d . . .
H13 H 0.4065 0.7061 0.3416 0.069 Uiso 1 1 calc R . .
C14 C 0.6390(3) 0.7955(2) 0.28645(7) 0.0544(4) Uani 1 1 d . . .
H14 H 0.7353 0.8543 0.3151 0.065 Uiso 1 1 calc R . .
C15 C 0.6926(3) 0.79781(19) 0.22779(7) 0.0475(4) Uani 1 1 d . . .
H15 H 0.8215 0.8611 0.2169 0.057 Uiso 1 1 calc R . .
O1 O 0.6099(2) 0.56307(13) 0.09764(5) 0.0573(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 1.396(2) . ?
C1 C6 1.4104(19) . ?
C1 C9 1.4920(19) . ?
C2 C3 1.376(2) . ?
C2 H2 0.9300 . ?
C3 C8 1.390(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.341(2) . ?
C4 C8 1.4270(19) 3_775 ?
C4 H4 0.9300 . ?
C5 C6 1.4388(19) . ?
C5 H5 0.9300 . ?
C6 C7 1.4251(19) . ?
C7 C8 1.4257(19) . ?
C7 C7 1.427(3) 3_775 ?
C8 C4 1.4270(19) 3_775 ?
C9 O1 1.2207(17) . ?
C9 C10 1.494(2) . ?
C10 C15 1.386(2) . ?
C10 C11 1.387(2) . ?
C11 C12 1.375(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(2) . ?
C14 H14 0.9300 . ?
C15 H15 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 119.64(13) . . ?
C2 C1 C9 117.50(13) . . ?
C6 C1 C9 122.68(12) . . ?
C3 C2 C1 121.68(13) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C8 120.60(13) . . ?
C2 C3 H3 119.7 . . ?
C8 C3 H3 119.7 . . ?
C5 C4 C8 121.85(13) . 3_775 ?
C5 C4 H4 119.1 . . ?
C8 C4 H4 119.1 3_775 . ?
C4 C5 C6 121.82(13) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C7 118.84(12) . . ?
C1 C6 C5 123.55(13) . . ?
C7 C6 C5 117.60(12) . . ?
C6 C7 C8 119.95(12) . . ?
C6 C7 C7 120.73(15) . 3_775 ?
C8 C7 C7 119.31(15) . 3_775 ?
C3 C8 C7 119.27(13) . . ?
C3 C8 C4 122.05(13) . 3_775 ?
C7 C8 C4 118.67(13) . 3_775 ?
O1 C9 C1 122.25(13) . . ?
O1 C9 C10 119.38(13) . . ?
C1 C9 C10 118.34(12) . . ?
C15 C10 C11 119.07(14) . . ?
C15 C10 C9 121.61(13) . . ?
C11 C10 C9 119.19(14) . . ?
C12 C11 C10 120.28(15) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 120.27(15) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 120.10(15) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.99(16) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 120.23(14) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.8(2) . . . . ?
C9 C1 C2 C3 -174.53(13) . . . . ?
C1 C2 C3 C8 -1.3(2) . . . . ?
C8 C4 C5 C6 -0.2(2) 3_775 . . . ?
C2 C1 C6 C7 0.2(2) . . . . ?
C9 C1 C6 C7 175.30(12) . . . . ?
C2 C1 C6 C5 178.97(13) . . . . ?
C9 C1 C6 C5 -5.9(2) . . . . ?
C4 C5 C6 C1 -179.58(14) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C1 C6 C7 C8 -0.73(19) . . . . ?
C5 C6 C7 C8 -179.56(12) . . . . ?
C1 C6 C7 C7 -179.82(15) . . . 3_775 ?
C5 C6 C7 C7 1.3(2) . . . 3_775 ?
C2 C3 C8 C7 0.8(2) . . . . ?
C2 C3 C8 C4 179.98(13) . . . 3_775 ?
C6 C7 C8 C3 0.3(2) . . . . ?
C7 C7 C8 C3 179.36(15) 3_775 . . . ?
C6 C7 C8 C4 -178.99(12) . . . 3_775 ?
C7 C7 C8 C4 0.1(2) 3_775 . . 3_775 ?
C2 C1 C9 O1 139.10(15) . . . . ?
C6 C1 C9 O1 -36.1(2) . . . . ?
C2 C1 C9 C10 -38.99(19) . . . . ?
C6 C1 C9 C10 145.82(14) . . . . ?
O1 C9 C10 C15 137.57(15) . . . . ?
C1 C9 C10 C15 -44.3(2) . . . . ?
O1 C9 C10 C11 -38.4(2) . . . . ?
C1 C9 C10 C11 139.76(15) . . . . ?
C15 C10 C11 C12 0.7(2) . . . . ?
C9 C10 C11 C12 176.81(15) . . . . ?
C10 C11 C12 C13 -2.1(3) . . . . ?
C11 C12 C13 C14 1.3(3) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C13 C14 C15 C10 -2.2(2) . . . . ?
C11 C10 C15 C14 1.4(2) . . . . ?
C9 C10 C15 C14 -174.57(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.70
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.030
_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_di_benzyl_pyr
_database_code_depnum_ccdc_archive 'CCDC 1440154'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        pyrene-1,8-diylbis(phenylmethanone)
_chemical_name_common            '1,8 Dibenzoylpyrene'
_chemical_melting_point          428.15
_chemical_formula_moiety         'C30 H18 O2'
_chemical_formula_sum            'C30 H18 O2'
_chemical_formula_weight         410.44
_chemical_absolute_configuration rm

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   25.1722(5)
_cell_length_b                   8.4269(2)
_cell_length_c                   19.6579(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.8860(10)
_cell_angle_gamma                90.00
_cell_volume                     4107.99(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6494
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      28.19

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      1.326
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1712
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9838
_exptl_absorpt_correction_T_max  0.9878
_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         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15377
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3604
_reflns_number_gt                2743
_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)+(0.0810P)²+1.5787P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0083(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3604
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1600
_refine_ls_wR_factor_gt          0.1237
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_restrained_S_all      1.155
_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 0.03629(8) 0.1360(2) 0.09989(10) 0.0532(5) Uani 1 1 d . . .
C2 C 0.09220(7) 0.0369(2) 0.20836(9) 0.0517(5) Uani 1 1 d . . .
H2 H 0.0651 0.0625 0.2332 0.062 Uiso 1 1 calc R . .
C3 C 0.13872(8) -0.0250(2) 0.24203(10) 0.0533(5) Uani 1 1 d . . .
H3 H 0.1429 -0.0402 0.2895 0.064 Uiso 1 1 calc R . .
C4 C 0.23143(7) -0.1316(2) 0.24063(11) 0.0550(5) Uani 1 1 d . . .
C5 C 0.27160(8) -0.1705(2) 0.20267(13) 0.0647(6) Uani 1 1 d . . .
H5 H 0.3044 -0.2100 0.2254 0.078 Uiso 1 1 calc R . .
C6 C 0.26351(8) -0.1513(2) 0.13195(13) 0.0649(6) Uani 1 1 d . . .
H6 H 0.2905 -0.1807 0.1076 0.078 Uiso 1 1 calc R . .
C7 C 0.20566(9) -0.0671(3) 0.02272(12) 0.0658(6) Uani 1 1 d . . .
H7 H 0.2319 -0.0980 -0.0025 0.079 Uiso 1 1 calc R . .
C8 C 0.15985(9) -0.0041(3) -0.01030(11) 0.0667(6) Uani 1 1 d . . .
H8 H 0.1550 0.0080 -0.0580 0.080 Uiso 1 1 calc R . .
C9 C 0.07114(9) 0.1203(3) -0.00652(11) 0.0666(6) Uani 1 1 d . . .
H9 H 0.0665 0.1391 -0.0538 0.080 Uiso 1 1 calc R . .
C10 C 0.03159(9) 0.1672(3) 0.02963(11) 0.0657(6) Uani 1 1 d . . .
H10 H 0.0014 0.2205 0.0068 0.079 Uiso 1 1 calc R . .
C11 C 0.08345(7) 0.0644(2) 0.13541(9) 0.0471(4) Uani 1 1 d . . .
C12 C 0.12513(7) 0.0221(2) 0.09857(9) 0.0476(4) Uani 1 1 d . . .
C13 C 0.11776(8) 0.0458(2) 0.02597(10) 0.0564(5) Uani 1 1 d . . .
C14 C 0.21555(8) -0.0887(2) 0.09658(11) 0.0566(5) Uani 1 1 d . . .
C15 C 0.17437(7) -0.0444(2) 0.13423(10) 0.0481(4) Uani 1 1 d . . .
C16 C 0.18199(7) -0.0684(2) 0.20680(10) 0.0495(5) Uani 1 1 d . . .
C17 C -0.01079(7) 0.1693(2) 0.13539(10) 0.0541(5) Uani 1 1 d . . .
C18 C -0.02813(7) 0.3351(2) 0.14357(10) 0.0544(5) Uani 1 1 d . . .
C19 C 0.00612(9) 0.4611(3) 0.13891(13) 0.0709(6) Uani 1 1 d . . .
H19 H 0.0399 0.4430 0.1274 0.085 Uiso 1 1 calc R . .
C20 C -0.00963(11) 0.6139(3) 0.15134(14) 0.0842(7) Uani 1 1 d . . .
H20 H 0.0137 0.6983 0.1484 0.101 Uiso 1 1 calc R . .
C21 C -0.05948(11) 0.6414(3) 0.16796(13) 0.0818(7) Uani 1 1 d . . .
H21 H -0.0698 0.7443 0.1768 0.098 Uiso 1 1 calc R . .
C22 C -0.09394(10) 0.5181(3) 0.17157(13) 0.0804(7) Uani 1 1 d . . .
H22 H -0.1281 0.5375 0.1818 0.096 Uiso 1 1 calc R . .
C23 C -0.07854(8) 0.3653(3) 0.16016(11) 0.0671(6) Uani 1 1 d . . .
H23 H -0.1020 0.2816 0.1636 0.081 Uiso 1 1 calc R . .
C24 C 0.23954(8) -0.1661(2) 0.31648(11) 0.0606(5) Uani 1 1 d . . .
C25 C 0.28665(8) -0.0985(2) 0.36368(11) 0.0580(5) Uani 1 1 d . . .
C26 C 0.29406(9) -0.1427(3) 0.43257(12) 0.0735(6) Uani 1 1 d . . .
H26 H 0.2711 -0.2169 0.4473 0.088 Uiso 1 1 calc R . .
C27 C 0.33507(12) -0.0774(4) 0.47915(15) 0.0955(9) Uani 1 1 d . . .
H27 H 0.3399 -0.1080 0.5253 0.115 Uiso 1 1 calc R . .
C28 C 0.36900(11) 0.0324(4) 0.45821(19) 0.0981(10) Uani 1 1 d . . .
H28 H 0.3966 0.0765 0.4901 0.118 Uiso 1 1 calc R . .
C29 C 0.36226(9) 0.0773(3) 0.39007(18) 0.0838(8) Uani 1 1 d . . .
H29 H 0.3855 0.1514 0.3759 0.101 Uiso 1 1 calc R . .
C30 C 0.32107(8) 0.0128(2) 0.34232(13) 0.0659(6) Uani 1 1 d . . .
H30 H 0.3165 0.0438 0.2963 0.079 Uiso 1 1 calc R . .
O1 O -0.03459(6) 0.05861(18) 0.15658(8) 0.0736(5) Uani 1 1 d . . .
O2 O 0.20652(7) -0.2476(2) 0.33905(10) 0.0909(6) 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 C10 1.391(3) . ?
C1 C11 1.406(3) . ?
C1 C17 1.501(3) . ?
C2 C3 1.348(3) . ?
C2 C11 1.432(3) . ?
C2 H2 0.9300 . ?
C3 C16 1.435(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(3) . ?
C4 C16 1.411(3) . ?
C4 C24 1.498(3) . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C6 C14 1.390(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.333(3) . ?
C7 C14 1.442(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.438(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(3) . ?
C9 C13 1.386(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.419(2) . ?
C12 C13 1.421(3) . ?
C12 C15 1.429(3) . ?
C14 C15 1.423(3) . ?
C15 C16 1.421(3) . ?
C17 O1 1.220(2) . ?
C17 C18 1.480(3) . ?
C18 C19 1.380(3) . ?
C18 C23 1.387(3) . ?
C19 C20 1.382(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.370(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.363(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.375(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 O2 1.219(2) . ?
C24 C25 1.488(3) . ?
C25 C26 1.386(3) . ?
C25 C30 1.390(3) . ?
C26 C27 1.372(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.369(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.374(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.385(3) . ?
C29 H29 0.9300 . ?
C30 H30 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
C10 C1 C11 119.68(18) . . ?
C10 C1 C17 119.11(17) . . ?
C11 C1 C17 121.08(16) . . ?
C3 C2 C11 121.72(17) . . ?
C3 C2 H2 119.1 . . ?
C11 C2 H2 119.1 . . ?
C2 C3 C16 121.96(17) . . ?
C2 C3 H3 119.0 . . ?
C16 C3 H3 119.0 . . ?
C5 C4 C16 119.89(19) . . ?
C5 C4 C24 119.95(18) . . ?
C16 C4 C24 120.06(17) . . ?
C6 C5 C4 121.10(19) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C14 120.92(19) . . ?
C5 C6 H6 119.5 . . ?
C14 C6 H6 119.5 . . ?
C8 C7 C14 121.76(19) . . ?
C8 C7 H7 119.1 . . ?
C14 C7 H7 119.1 . . ?
C7 C8 C13 121.64(19) . . ?
C7 C8 H8 119.2 . . ?
C13 C8 H8 119.2 . . ?
C10 C9 C13 121.47(19) . . ?
C10 C9 H9 119.3 . . ?
C13 C9 H9 119.3 . . ?
C9 C10 C1 120.8(2) . . ?
C9 C10 H10 119.6 . . ?
C1 C10 H10 119.6 . . ?
C1 C11 C12 119.32(16) . . ?
C1 C11 C2 122.58(17) . . ?
C12 C11 C2 118.06(16) . . ?
C11 C12 C13 119.78(17) . . ?
C11 C12 C15 120.21(16) . . ?
C13 C12 C15 120.01(16) . . ?
C9 C13 C12 118.72(18) . . ?
C9 C13 C8 122.79(19) . . ?
C12 C13 C8 118.46(19) . . ?
C6 C14 C15 119.17(19) . . ?
C6 C14 C7 122.47(19) . . ?
C15 C14 C7 118.37(19) . . ?
C16 C15 C14 120.00(17) . . ?
C16 C15 C12 120.29(16) . . ?
C14 C15 C12 119.71(17) . . ?
C4 C16 C15 118.89(17) . . ?
C4 C16 C3 123.36(17) . . ?
C15 C16 C3 117.75(17) . . ?
O1 C17 C18 120.89(17) . . ?
O1 C17 C1 119.23(18) . . ?
C18 C17 C1 119.88(16) . . ?
C19 C18 C23 118.8(2) . . ?
C19 C18 C17 121.28(18) . . ?
C23 C18 C17 119.81(18) . . ?
C18 C19 C20 120.2(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C20 120.0(2) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.4(2) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 120.4(2) . . ?
C22 C23 H23 119.8 . . ?
C18 C23 H23 119.8 . . ?
O2 C24 C25 120.6(2) . . ?
O2 C24 C4 119.11(19) . . ?
C25 C24 C4 120.27(17) . . ?
C26 C25 C30 119.4(2) . . ?
C26 C25 C24 117.7(2) . . ?
C30 C25 C24 122.8(2) . . ?
C27 C26 C25 120.3(3) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C28 C27 C26 120.5(3) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C29 120.0(3) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 C30 120.4(3) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C29 C30 C25 119.5(2) . . ?
C29 C30 H30 120.2 . . ?
C25 C30 H30 120.2 . . ?

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
C11 C2 C3 C16 -0.5(3) . . . . ?
C16 C4 C5 C6 -1.4(3) . . . . ?
C24 C4 C5 C6 174.95(18) . . . . ?
C4 C5 C6 C14 1.7(3) . . . . ?
C14 C7 C8 C13 0.0(3) . . . . ?
C13 C9 C10 C1 -2.4(4) . . . . ?
C11 C1 C10 C9 4.0(3) . . . . ?
C17 C1 C10 C9 -171.9(2) . . . . ?
C10 C1 C11 C12 -1.3(3) . . . . ?
C17 C1 C11 C12 174.48(16) . . . . ?
C10 C1 C11 C2 176.46(18) . . . . ?
C17 C1 C11 C2 -7.7(3) . . . . ?
C3 C2 C11 C1 -176.86(18) . . . . ?
C3 C2 C11 C12 1.0(3) . . . . ?
C1 C11 C12 C13 -2.8(3) . . . . ?
C2 C11 C12 C13 179.27(16) . . . . ?
C1 C11 C12 C15 177.27(16) . . . . ?
C2 C11 C12 C15 -0.6(3) . . . . ?
C10 C9 C13 C12 -1.8(3) . . . . ?
C10 C9 C13 C8 -179.8(2) . . . . ?
C11 C12 C13 C9 4.4(3) . . . . ?
C15 C12 C13 C9 -175.69(17) . . . . ?
C11 C12 C13 C8 -177.55(17) . . . . ?
C15 C12 C13 C8 2.3(3) . . . . ?
C7 C8 C13 C9 176.0(2) . . . . ?
C7 C8 C13 C12 -1.9(3) . . . . ?
C5 C6 C14 C15 -0.1(3) . . . . ?
C5 C6 C14 C7 -179.95(19) . . . . ?
C8 C7 C14 C6 -178.7(2) . . . . ?
C8 C7 C14 C15 1.5(3) . . . . ?
C6 C14 C15 C16 -1.7(3) . . . . ?
C7 C14 C15 C16 178.11(16) . . . . ?
C6 C14 C15 C12 179.17(17) . . . . ?
C7 C14 C15 C12 -1.0(3) . . . . ?
C11 C12 C15 C16 -0.1(3) . . . . ?
C13 C12 C15 C16 179.99(16) . . . . ?
C11 C12 C15 C14 178.99(16) . . . . ?
C13 C12 C15 C14 -0.9(3) . . . . ?
C5 C4 C16 C15 -0.5(3) . . . . ?
C24 C4 C16 C15 -176.81(16) . . . . ?
C5 C4 C16 C3 -179.87(18) . . . . ?
C24 C4 C16 C3 3.8(3) . . . . ?
C14 C15 C16 C4 2.0(3) . . . . ?
C12 C15 C16 C4 -178.88(15) . . . . ?
C14 C15 C16 C3 -178.56(16) . . . . ?
C12 C15 C16 C3 0.5(2) . . . . ?
C2 C3 C16 C4 179.17(17) . . . . ?
C2 C3 C16 C15 -0.2(3) . . . . ?
C10 C1 C17 O1 111.8(2) . . . . ?
C11 C1 C17 O1 -64.0(3) . . . . ?
C10 C1 C17 C18 -67.5(3) . . . . ?
C11 C1 C17 C18 116.6(2) . . . . ?
O1 C17 C18 C19 160.9(2) . . . . ?
C1 C17 C18 C19 -19.8(3) . . . . ?
O1 C17 C18 C23 -15.3(3) . . . . ?
C1 C17 C18 C23 163.96(18) . . . . ?
C23 C18 C19 C20 0.7(3) . . . . ?
C17 C18 C19 C20 -175.6(2) . . . . ?
C18 C19 C20 C21 -0.4(4) . . . . ?
C19 C20 C21 C22 -0.7(4) . . . . ?
C20 C21 C22 C23 1.5(4) . . . . ?
C21 C22 C23 C18 -1.2(4) . . . . ?
C19 C18 C23 C22 0.1(3) . . . . ?
C17 C18 C23 C22 176.5(2) . . . . ?
C5 C4 C24 O2 -123.8(2) . . . . ?
C16 C4 C24 O2 52.5(3) . . . . ?
C5 C4 C24 C25 57.6(3) . . . . ?
C16 C4 C24 C25 -126.1(2) . . . . ?
O2 C24 C25 C26 5.5(3) . . . . ?
C4 C24 C25 C26 -175.88(18) . . . . ?
O2 C24 C25 C30 -170.6(2) . . . . ?
C4 C24 C25 C30 8.0(3) . . . . ?
C30 C25 C26 C27 -0.2(3) . . . . ?
C24 C25 C26 C27 -176.4(2) . . . . ?
C25 C26 C27 C28 0.2(4) . . . . ?
C26 C27 C28 C29 -0.3(4) . . . . ?
C27 C28 C29 C30 0.4(4) . . . . ?
C28 C29 C30 C25 -0.3(3) . . . . ?
C26 C25 C30 C29 0.2(3) . . . . ?
C24 C25 C30 C29 176.29(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.178
_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_tri_benzyl
_database_code_depnum_ccdc_archive 'CCDC 1440155'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        pyrene-1,3,6-triyltris(phenylmethanone)
_chemical_name_common            Tribenzoylpyrene
_chemical_melting_point          456.15
_chemical_formula_moiety         'C37 H22 O3'
_chemical_formula_sum            'C37 H22 O3'
_chemical_formula_weight         514.55

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                   8.9515(4)
_cell_length_b                   11.9373(5)
_cell_length_c                   14.2375(6)
_cell_angle_alpha                104.703(2)
_cell_angle_beta                 102.280(2)
_cell_angle_gamma                109.581(2)
_cell_volume                     1310.36(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3201
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      27.44

_exptl_crystal_description       block37
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      1.303
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9838
_exptl_absorpt_correction_T_max  0.9878
_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         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16670
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         23.25
_reflns_number_total             3736
_reflns_number_gt                2350
_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+0.0112P] 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         3736
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1610
_refine_ls_wR_factor_gt          0.1140
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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 0.3928(3) 0.1207(2) -0.02994(19) 0.0385(7) Uani 1 1 d . . .
C2 C 0.5115(3) 0.2454(2) 0.0033(2) 0.0427(7) Uani 1 1 d . . .
H2 H 0.5760 0.2686 -0.0375 0.051 Uiso 1 1 calc R . .
C3 C 0.5371(3) 0.3365(2) 0.0952(2) 0.0403(7) Uani 1 1 d . . .
C4 C 0.4655(3) 0.3936(3) 0.2552(2) 0.0440(7) Uani 1 1 d . . .
H4 H 0.5422 0.4774 0.2752 0.053 Uiso 1 1 calc R . .
C5 C 0.3801(3) 0.3603(3) 0.3176(2) 0.0458(7) Uani 1 1 d . . .
H5 H 0.3988 0.4213 0.3794 0.055 Uiso 1 1 calc R . .
C6 C 0.1658(3) 0.1943(3) 0.3536(2) 0.0472(7) Uani 1 1 d . . .
C7 C 0.0507(4) 0.0682(3) 0.3222(2) 0.0576(8) Uani 1 1 d . . .
H7 H -0.0133 0.0442 0.3630 0.069 Uiso 1 1 calc R . .
C8 C 0.0299(3) -0.0213(3) 0.2321(2) 0.0567(8) Uani 1 1 d . . .
H8 H -0.0442 -0.1054 0.2146 0.068 Uiso 1 1 calc R . .
C9 C 0.0957(3) -0.0775(3) 0.0717(2) 0.0495(8) Uani 1 1 d . . .
H9 H 0.0206 -0.1615 0.0528 0.059 Uiso 1 1 calc R . .
C10 C 0.1794(3) -0.0446(3) 0.0084(2) 0.0462(7) Uani 1 1 d . . .
H10 H 0.1593 -0.1061 -0.0536 0.055 Uiso 1 1 calc R . .
C11 C 0.2994(3) 0.0832(2) 0.0335(2) 0.0379(7) Uani 1 1 d . . .
C12 C 0.3242(3) 0.1762(2) 0.1282(2) 0.0372(7) Uani 1 1 d . . .
C13 C 0.4427(3) 0.3044(2) 0.1586(2) 0.0375(7) Uani 1 1 d . . .
C14 C 0.1181(3) 0.0120(3) 0.1670(2) 0.0442(7) Uani 1 1 d . . .
C15 C 0.2336(3) 0.1405(2) 0.1951(2) 0.0380(7) Uani 1 1 d . . .
C16 C 0.2607(3) 0.2325(3) 0.2910(2) 0.0409(7) Uani 1 1 d . . .
C17 C 0.6684(3) 0.4689(3) 0.1234(2) 0.0452(7) Uani 1 1 d . . .
C18 C 0.8421(3) 0.4845(2) 0.12829(19) 0.0405(7) Uani 1 1 d . . .
C19 C 0.8986(3) 0.3914(3) 0.1364(2) 0.0482(8) Uani 1 1 d . . .
H19 H 0.8257 0.3148 0.1367 0.058 Uiso 1 1 calc R . .
C20 C 1.0621(4) 0.4118(3) 0.1441(2) 0.0586(9) Uani 1 1 d . . .
H20 H 1.0987 0.3486 0.1491 0.070 Uiso 1 1 calc R . .
C21 C 1.1715(4) 0.5244(3) 0.1444(2) 0.0648(9) Uani 1 1 d . . .
H21 H 1.2818 0.5375 0.1495 0.078 Uiso 1 1 calc R . .
C22 C 1.1177(4) 0.6176(3) 0.1372(2) 0.0640(9) Uani 1 1 d . . .
H22 H 1.1918 0.6942 0.1376 0.077 Uiso 1 1 calc R . .
C23 C 0.9542(4) 0.5983(3) 0.1294(2) 0.0529(8) Uani 1 1 d . . .
H23 H 0.9188 0.6622 0.1248 0.063 Uiso 1 1 calc R . .
C24 C 0.3830(3) 0.0292(3) -0.1273(2) 0.0423(7) Uani 1 1 d . . .
C25 C 0.4249(3) 0.0757(3) -0.2105(2) 0.0436(7) Uani 1 1 d . . .
C26 C 0.4961(4) 0.0147(3) -0.2720(3) 0.0648(9) Uani 1 1 d . . .
H26 H 0.5198 -0.0514 -0.2597 0.078 Uiso 1 1 calc R . .
C27 C 0.5315(5) 0.0528(4) -0.3516(3) 0.0899(12) Uani 1 1 d . . .
H27 H 0.5818 0.0134 -0.3917 0.108 Uiso 1 1 calc R . .
C28 C 0.4935(6) 0.1473(4) -0.3721(3) 0.0913(13) Uani 1 1 d . . .
H28 H 0.5170 0.1715 -0.4264 0.110 Uiso 1 1 calc R . .
C29 C 0.4207(4) 0.2068(3) -0.3130(3) 0.0694(10) Uani 1 1 d . . .
H29 H 0.3924 0.2699 -0.3280 0.083 Uiso 1 1 calc R . .
C30 C 0.3897(3) 0.1731(3) -0.2315(2) 0.0499(8) Uani 1 1 d . . .
H30 H 0.3444 0.2161 -0.1900 0.060 Uiso 1 1 calc R . .
C31 C 0.1878(4) 0.2861(3) 0.4550(2) 0.0516(8) Uani 1 1 d . . .
C32 C 0.0380(4) 0.3032(3) 0.4718(2) 0.0517(8) Uani 1 1 d . . .
C33 C 0.0328(4) 0.3471(4) 0.5701(3) 0.0786(11) Uani 1 1 d . . .
H33 H 0.1212 0.3613 0.6261 0.094 Uiso 1 1 calc R . .
C34 C -0.1022(5) 0.3698(4) 0.5855(3) 0.0961(13) Uani 1 1 d . . .
H34 H -0.1050 0.3983 0.6520 0.115 Uiso 1 1 calc R . .
C35 C -0.2317(5) 0.3513(4) 0.5048(4) 0.0876(12) Uani 1 1 d . . .
H35 H -0.3220 0.3680 0.5161 0.105 Uiso 1 1 calc R . .
C36 C -0.2288(5) 0.3084(4) 0.4076(3) 0.0812(11) Uani 1 1 d . . .
H36 H -0.3170 0.2961 0.3523 0.097 Uiso 1 1 calc R . .
C37 C -0.0953(4) 0.2829(3) 0.3904(2) 0.0662(9) Uani 1 1 d . . .
H37 H -0.0955 0.2517 0.3235 0.079 Uiso 1 1 calc R . .
O1 O 0.3459(3) -0.08384(19) -0.14002(15) 0.0576(6) Uani 1 1 d . . .
O2 O 0.6319(3) 0.55956(19) 0.14252(19) 0.0723(7) Uani 1 1 d . . .
O3 O 0.3253(3) 0.3444(2) 0.52139(15) 0.0720(7) 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 1.392(3) . ?
C1 C11 1.411(3) . ?
C1 C24 1.496(4) . ?
C2 C3 1.389(4) . ?
C2 H2 0.9300 . ?
C3 C13 1.399(4) . ?
C3 C17 1.508(4) . ?
C4 C5 1.341(4) . ?
C4 C13 1.434(4) . ?
C4 H4 0.9300 . ?
C5 C16 1.433(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.397(4) . ?
C6 C16 1.412(4) . ?
C6 C31 1.501(4) . ?
C7 C8 1.374(4) . ?
C7 H7 0.9300 . ?
C8 C14 1.390(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.341(4) . ?
C9 C14 1.423(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.438(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.430(4) . ?
C12 C13 1.427(3) . ?
C12 C15 1.432(3) . ?
C14 C15 1.426(4) . ?
C15 C16 1.431(4) . ?
C17 O2 1.216(3) . ?
C17 C18 1.486(4) . ?
C18 C23 1.386(4) . ?
C18 C19 1.387(4) . ?
C19 C20 1.375(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.371(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.369(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 O1 1.230(3) . ?
C24 C25 1.495(4) . ?
C25 C30 1.387(4) . ?
C25 C26 1.389(4) . ?
C26 C27 1.382(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.363(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.371(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.372(4) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 O3 1.221(3) . ?
C31 C32 1.481(4) . ?
C32 C37 1.379(4) . ?
C32 C33 1.380(4) . ?
C33 C34 1.372(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.359(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.357(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.382(5) . ?
C36 H36 0.9300 . ?
C37 H37 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 119.2(2) . . ?
C2 C1 C24 117.6(2) . . ?
C11 C1 C24 122.9(2) . . ?
C3 C2 C1 122.4(2) . . ?
C3 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
C2 C3 C13 120.2(2) . . ?
C2 C3 C17 117.9(2) . . ?
C13 C3 C17 121.9(2) . . ?
C5 C4 C13 122.3(3) . . ?
C5 C4 H4 118.9 . . ?
C13 C4 H4 118.9 . . ?
C4 C5 C16 121.4(3) . . ?
C4 C5 H5 119.3 . . ?
C16 C5 H5 119.3 . . ?
C7 C6 C16 119.8(3) . . ?
C7 C6 C31 118.8(2) . . ?
C16 C6 C31 121.4(3) . . ?
C8 C7 C6 121.5(3) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C14 120.9(3) . . ?
C7 C8 H8 119.5 . . ?
C14 C8 H8 119.5 . . ?
C10 C9 C14 122.2(3) . . ?
C10 C9 H9 118.9 . . ?
C14 C9 H9 118.9 . . ?
C9 C10 C11 121.8(3) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C1 C11 C12 118.9(2) . . ?
C1 C11 C10 123.5(2) . . ?
C12 C11 C10 117.7(2) . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 C15 119.2(2) . . ?
C11 C12 C15 120.2(2) . . ?
C3 C13 C12 118.6(2) . . ?
C3 C13 C4 122.8(2) . . ?
C12 C13 C4 118.5(2) . . ?
C8 C14 C9 122.4(3) . . ?
C8 C14 C15 119.2(3) . . ?
C9 C14 C15 118.4(3) . . ?
C14 C15 C16 119.8(2) . . ?
C14 C15 C12 119.8(2) . . ?
C16 C15 C12 120.4(2) . . ?
C6 C16 C15 118.7(2) . . ?
C6 C16 C5 123.1(3) . . ?
C15 C16 C5 118.2(2) . . ?
O2 C17 C18 121.6(2) . . ?
O2 C17 C3 120.2(3) . . ?
C18 C17 C3 118.2(2) . . ?
C23 C18 C19 118.5(3) . . ?
C23 C18 C17 119.0(3) . . ?
C19 C18 C17 122.3(2) . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 120.6(3) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 119.8(3) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C23 120.2(3) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C18 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
O1 C24 C25 118.4(3) . . ?
O1 C24 C1 121.7(2) . . ?
C25 C24 C1 119.8(2) . . ?
C30 C25 C26 118.7(3) . . ?
C30 C25 C24 123.0(3) . . ?
C26 C25 C24 118.2(3) . . ?
C27 C26 C25 119.6(3) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C28 C27 C26 120.8(4) . . ?
C28 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C27 C28 C29 120.1(4) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 C30 119.9(3) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C29 C30 C25 120.8(3) . . ?
C29 C30 H30 119.6 . . ?
C25 C30 H30 119.6 . . ?
O3 C31 C32 121.3(3) . . ?
O3 C31 C6 120.7(3) . . ?
C32 C31 C6 118.0(2) . . ?
C37 C32 C33 118.3(3) . . ?
C37 C32 C31 121.0(3) . . ?
C33 C32 C31 120.6(3) . . ?
C34 C33 C32 120.4(3) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C35 C34 C33 120.8(4) . . ?
C35 C34 H34 119.6 . . ?
C33 C34 H34 119.6 . . ?
C36 C35 C34 119.7(4) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
C35 C36 C37 120.4(3) . . ?
C35 C36 H36 119.8 . . ?
C37 C36 H36 119.8 . . ?
C32 C37 C36 120.4(3) . . ?
C32 C37 H37 119.8 . . ?
C36 C37 H37 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
C11 C1 C2 C3 -2.7(4) . . . . ?
C24 C1 C2 C3 -176.7(2) . . . . ?
C1 C2 C3 C13 0.3(4) . . . . ?
C1 C2 C3 C17 -179.7(2) . . . . ?
C13 C4 C5 C16 0.2(4) . . . . ?
C16 C6 C7 C8 1.6(4) . . . . ?
C31 C6 C7 C8 -177.3(3) . . . . ?
C6 C7 C8 C14 -2.7(5) . . . . ?
C14 C9 C10 C11 1.0(4) . . . . ?
C2 C1 C11 C12 2.8(4) . . . . ?
C24 C1 C11 C12 176.4(2) . . . . ?
C2 C1 C11 C10 -177.1(2) . . . . ?
C24 C1 C11 C10 -3.6(4) . . . . ?
C9 C10 C11 C1 178.4(2) . . . . ?
C9 C10 C11 C12 -1.6(4) . . . . ?
C1 C11 C12 C13 -0.7(4) . . . . ?
C10 C11 C12 C13 179.3(2) . . . . ?
C1 C11 C12 C15 -178.9(2) . . . . ?
C10 C11 C12 C15 1.1(4) . . . . ?
C2 C3 C13 C12 1.8(4) . . . . ?
C17 C3 C13 C12 -178.1(2) . . . . ?
C2 C3 C13 C4 178.8(2) . . . . ?
C17 C3 C13 C4 -1.1(4) . . . . ?
C11 C12 C13 C3 -1.7(4) . . . . ?
C15 C12 C13 C3 176.6(2) . . . . ?
C11 C12 C13 C4 -178.8(2) . . . . ?
C15 C12 C13 C4 -0.5(4) . . . . ?
C5 C4 C13 C3 -176.7(2) . . . . ?
C5 C4 C13 C12 0.3(4) . . . . ?
C7 C8 C14 C9 -178.0(3) . . . . ?
C7 C8 C14 C15 1.0(4) . . . . ?
C10 C9 C14 C8 179.1(3) . . . . ?
C10 C9 C14 C15 0.1(4) . . . . ?
C8 C14 C15 C16 1.8(4) . . . . ?
C9 C14 C15 C16 -179.2(2) . . . . ?
C8 C14 C15 C12 -179.5(2) . . . . ?
C9 C14 C15 C12 -0.5(4) . . . . ?
C13 C12 C15 C14 -178.3(2) . . . . ?
C11 C12 C15 C14 -0.1(4) . . . . ?
C13 C12 C15 C16 0.3(4) . . . . ?
C11 C12 C15 C16 178.6(2) . . . . ?
C7 C6 C16 C15 1.2(4) . . . . ?
C31 C6 C16 C15 -179.9(2) . . . . ?
C7 C6 C16 C5 179.5(3) . . . . ?
C31 C6 C16 C5 -1.6(4) . . . . ?
C14 C15 C16 C6 -2.9(4) . . . . ?
C12 C15 C16 C6 178.5(2) . . . . ?
C14 C15 C16 C5 178.8(2) . . . . ?
C12 C15 C16 C5 0.1(4) . . . . ?
C4 C5 C16 C6 -178.6(3) . . . . ?
C4 C5 C16 C15 -0.3(4) . . . . ?
C2 C3 C17 O2 125.0(3) . . . . ?
C13 C3 C17 O2 -55.1(4) . . . . ?
C2 C3 C17 C18 -55.8(3) . . . . ?
C13 C3 C17 C18 124.1(3) . . . . ?
O2 C17 C18 C23 -16.2(4) . . . . ?
C3 C17 C18 C23 164.6(2) . . . . ?
O2 C17 C18 C19 160.9(3) . . . . ?
C3 C17 C18 C19 -18.3(4) . . . . ?
C23 C18 C19 C20 -0.8(4) . . . . ?
C17 C18 C19 C20 -177.9(2) . . . . ?
C18 C19 C20 C21 0.4(4) . . . . ?
C19 C20 C21 C22 0.1(5) . . . . ?
C20 C21 C22 C23 -0.2(5) . . . . ?
C21 C22 C23 C18 -0.3(5) . . . . ?
C19 C18 C23 C22 0.7(4) . . . . ?
C17 C18 C23 C22 177.9(2) . . . . ?
C2 C1 C24 O1 146.7(3) . . . . ?
C11 C1 C24 O1 -26.9(4) . . . . ?
C2 C1 C24 C25 -31.1(3) . . . . ?
C11 C1 C24 C25 155.2(2) . . . . ?
O1 C24 C25 C30 147.6(3) . . . . ?
C1 C24 C25 C30 -34.5(4) . . . . ?
O1 C24 C25 C26 -29.7(4) . . . . ?
C1 C24 C25 C26 148.2(3) . . . . ?
C30 C25 C26 C27 0.6(5) . . . . ?
C24 C25 C26 C27 178.0(3) . . . . ?
C25 C26 C27 C28 -1.7(6) . . . . ?
C26 C27 C28 C29 0.6(6) . . . . ?
C27 C28 C29 C30 1.5(6) . . . . ?
C28 C29 C30 C25 -2.6(5) . . . . ?
C26 C25 C30 C29 1.5(4) . . . . ?
C24 C25 C30 C29 -175.8(3) . . . . ?
C7 C6 C31 O3 122.7(3) . . . . ?
C16 C6 C31 O3 -56.2(4) . . . . ?
C7 C6 C31 C32 -57.2(4) . . . . ?
C16 C6 C31 C32 123.9(3) . . . . ?
O3 C31 C32 C37 153.0(3) . . . . ?
C6 C31 C32 C37 -27.1(4) . . . . ?
O3 C31 C32 C33 -23.2(4) . . . . ?
C6 C31 C32 C33 156.6(3) . . . . ?
C37 C32 C33 C34 -0.2(5) . . . . ?
C31 C32 C33 C34 176.2(3) . . . . ?
C32 C33 C34 C35 -0.9(6) . . . . ?
C33 C34 C35 C36 0.8(6) . . . . ?
C34 C35 C36 C37 0.4(6) . . . . ?
C33 C32 C37 C36 1.3(5) . . . . ?
C31 C32 C37 C36 -175.1(3) . . . . ?
C35 C36 C37 C32 -1.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        23.25
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.094
_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 1440156'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
pyrene-1,3,6,8-tetrayltetrakis(phenylmethanone)
_chemical_name_common            Tetrabenzoylpyrene
_chemical_melting_point          561.15
_chemical_formula_moiety         'C44 H26 O4'
_chemical_formula_sum            'C44 H26 O4'
_chemical_formula_weight         618.65
_chemical_absolute_configuration rm

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                   5.6503(16)
_cell_length_b                   20.897(5)
_cell_length_c                   12.787(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.506(12)
_cell_angle_gamma                90
_cell_volume                     1479.5(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3898
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      29.81

_exptl_crystal_description       rectangular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      1.388
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9783
_exptl_absorpt_correction_T_max  0.9912
_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            14254
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.538
_diffrn_reflns_theta_max         28.000
_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             3578
_reflns_number_gt                2655
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0706P)²+0.2577P] 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         3578
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1253
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 0.8775(3) 0.08469(6) 0.75771(11) 0.0317(3) Uani 1 1 d . . . . .
H1 H 0.8506 0.1081 0.6946 0.038 Uiso 1 1 calc R U . . .
C2 C 1.0452(3) 0.03525(6) 0.77034(10) 0.0292(3) Uani 1 1 d . . . . .
C3 C 1.1005(2) 0.00169(6) 0.86772(10) 0.0267(3) Uani 1 1 d . . . . .
C4 C 0.9723(2) 0.01676(5) 0.95003(10) 0.0250(3) Uani 1 1 d . . . . .
C5 C 0.7896(2) 0.06533(6) 0.93319(10) 0.0257(3) Uani 1 1 d . . . . .
C6 C 0.7487(3) 0.10038(6) 0.83597(10) 0.0288(3) Uani 1 1 d . . . . .
C7 C 0.6586(3) 0.07684(6) 1.01652(10) 0.0290(3) Uani 1 1 d . . . . .
H7 H 0.5346 0.1069 1.0057 0.035 Uiso 1 1 calc R U . . .
C8 C 1.2892(2) -0.04524(6) 0.88988(10) 0.0297(3) Uani 1 1 d . . . . .
H8 H 1.3785 -0.0541 0.8379 0.036 Uiso 1 1 calc R U . . .
C9 C 1.1696(3) 0.02243(6) 0.67860(11) 0.0325(3) Uani 1 1 d . . . . .
C10 C 1.1759(3) -0.04406(7) 0.63671(10) 0.0315(3) Uani 1 1 d . . . . .
C11 C 1.3522(3) -0.05935(8) 0.57857(12) 0.0426(4) Uani 1 1 d . . . . .
H11 H 1.4643 -0.0286 0.5683 0.051 Uiso 1 1 calc R U . . .
C12 C 1.3618(4) -0.11962(9) 0.53624(14) 0.0530(5) Uani 1 1 d . . . . .
H12 H 1.4803 -0.1296 0.4978 0.064 Uiso 1 1 calc R U . . .
C13 C 1.1953(4) -0.16521(9) 0.55096(14) 0.0562(5) Uani 1 1 d . . . . .
H13 H 1.2015 -0.2059 0.5221 0.067 Uiso 1 1 calc R U . . .
C14 C 1.0198(4) -0.15093(8) 0.60820(14) 0.0515(4) Uani 1 1 d . . . . .
H14 H 0.9078 -0.1819 0.6177 0.062 Uiso 1 1 calc R U . . .
C15 C 1.0098(3) -0.09039(7) 0.65176(12) 0.0390(4) Uani 1 1 d . . . . .
H15 H 0.8922 -0.0809 0.6909 0.047 Uiso 1 1 calc R U . . .
C16 C 0.5664(3) 0.15334(6) 0.81229(11) 0.0315(3) Uani 1 1 d . . . . .
C17 C 0.6080(3) 0.20533(6) 0.73712(11) 0.0318(3) Uani 1 1 d . . . . .
C18 C 0.8281(3) 0.23734(7) 0.74986(13) 0.0408(4) Uani 1 1 d . . . . .
H18 H 0.9602 0.2232 0.8000 0.049 Uiso 1 1 calc R U . . .
C19 C 0.8490(3) 0.29061(8) 0.68697(16) 0.0506(4) Uani 1 1 d . . . . .
H19 H 0.9934 0.3133 0.6972 0.061 Uiso 1 1 calc R U . . .
C20 C 0.6556(4) 0.30983(8) 0.60937(16) 0.0543(5) Uani 1 1 d . . . . .
H20 H 0.6707 0.3453 0.5672 0.065 Uiso 1 1 calc R U . . .
C21 C 0.4401(3) 0.27675(8) 0.59411(14) 0.0485(4) Uani 1 1 d . . . . .
H21 H 0.3122 0.2891 0.5402 0.058 Uiso 1 1 calc R U . . .
C22 C 0.4136(3) 0.22517(7) 0.65883(12) 0.0382(3) Uani 1 1 d . . . . .
H22 H 0.2665 0.2038 0.6501 0.046 Uiso 1 1 calc R U . . .
O1 O 1.2575(2) 0.06664(5) 0.63781(9) 0.0525(3) Uani 1 1 d . . . . .
O2 O 0.3874(2) 0.15638(5) 0.85195(9) 0.0463(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 C6 1.3889(19) . ?
C1 C2 1.3892(19) . ?
C1 H1 0.9300 . ?
C2 C3 1.4088(18) . ?
C2 C9 1.5070(18) . ?
C3 C4 1.4266(18) . ?
C3 C8 1.4349(18) . ?
C4 C5 1.4329(17) . ?
C4 C4 1.436(2) 3_757 ?
C5 C6 1.4215(17) . ?
C5 C7 1.4337(18) . ?
C6 C16 1.5009(18) . ?
C7 C8 1.3472(18) 3_757 ?
C7 H7 0.9300 . ?
C8 C7 1.3472(18) 3_757 ?
C8 H8 0.9300 . ?
C9 O1 1.2147(17) . ?
C9 C10 1.4921(19) . ?
C10 C15 1.388(2) . ?
C10 C11 1.394(2) . ?
C11 C12 1.376(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.388(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 O2 1.2205(18) . ?
C16 C17 1.4998(19) . ?
C17 C18 1.392(2) . ?
C17 C22 1.394(2) . ?
C18 C19 1.392(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.381(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.380(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(2) . ?
C21 H21 0.9300 . ?
C22 H22 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
C6 C1 C2 122.35(12) . . ?
C6 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 119.91(12) . . ?
C1 C2 C9 117.06(11) . . ?
C3 C2 C9 122.96(12) . . ?
C2 C3 C4 119.11(12) . . ?
C2 C3 C8 122.66(12) . . ?
C4 C3 C8 118.16(11) . . ?
C3 C4 C5 120.13(11) . . ?
C3 C4 C4 119.74(14) . 3_757 ?
C5 C4 C4 120.13(14) . 3_757 ?
C6 C5 C4 118.88(12) . . ?
C6 C5 C7 123.06(12) . . ?
C4 C5 C7 118.05(11) . . ?
C1 C6 C5 119.42(12) . . ?
C1 C6 C16 117.77(11) . . ?
C5 C6 C16 122.79(12) . . ?
C8 C7 C5 121.61(12) 3_757 . ?
C8 C7 H7 119.2 3_757 . ?
C5 C7 H7 119.2 . . ?
C7 C8 C3 122.19(12) 3_757 . ?
C7 C8 H8 118.9 3_757 . ?
C3 C8 H8 118.9 . . ?
O1 C9 C10 120.87(13) . . ?
O1 C9 C2 119.54(12) . . ?
C10 C9 C2 119.56(11) . . ?
C15 C10 C11 119.27(14) . . ?
C15 C10 C9 122.30(13) . . ?
C11 C10 C9 118.41(13) . . ?
C12 C11 C10 120.52(16) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 119.85(16) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.41(16) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.12(17) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 119.82(15) . . ?
C14 C15 H15 120.1 . . ?
C10 C15 H15 120.1 . . ?
O2 C16 C17 118.52(12) . . ?
O2 C16 C6 123.16(12) . . ?
C17 C16 C6 118.32(12) . . ?
C18 C17 C22 119.90(13) . . ?
C18 C17 C16 121.57(13) . . ?
C22 C17 C16 118.29(14) . . ?
C19 C18 C17 119.56(15) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C20 C19 C18 120.11(17) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 120.35(15) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 120.19(16) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 119.81(16) . . ?
C21 C22 H22 120.1 . . ?
C17 C22 H22 120.1 . . ?

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.037

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3:Acetone'
