# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_i14607
_database_code_depnum_ccdc_archive 'CCDC 1401393'
_audit_update_record             
;
2015-05-17 deposited with the CCDC.
2015-06-22 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H8'
_chemical_formula_sum            'C17 H8'
_chemical_formula_weight         212.23

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.5659(4)
_cell_length_b                   5.13300(10)
_cell_length_c                   15.5436(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.063(2)
_cell_angle_gamma                90
_cell_volume                     922.79(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    6596
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      29.64

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       niddle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.84
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.421
-1 0 0 0.399
0 0 -1 0.055
0 0 1 0.067
0 -1 0 0.053
0 1 0 0.055

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_correction_T_min  0.9306
_exptl_absorpt_correction_T_max  0.9905

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_number            22871
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             1892
_reflns_number_gt                1367
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2sigma(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)+(0.0604P)²+0.6927P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1892
_refine_ls_number_parameters     154
_refine_ls_number_restraints     49
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1419
_refine_ls_wR_factor_gt          0.1263
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.054

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.87244(14) -0.3453(3) -0.07349(11) 0.0159(4) Uani 1 1 d U . .
C2 C 0.77963(15) -0.5008(3) -0.10231(11) 0.0177(4) Uani 1 1 d U . .
H2 H 0.7932 -0.6329 -0.1439 0.021 Uiso 1 1 calc R . .
C3 C 0.66991(15) -0.4634(4) -0.07099(12) 0.0219(4) Uani 1 1 d U . .
H3 H 0.6079 -0.5667 -0.0921 0.026 Uiso 1 1 calc R . .
C4 C 0.64918(15) -0.2751(3) -0.00860(12) 0.0205(4) Uani 1 1 d U . .
H4 H 0.573 -0.2524 0.0129 0.025 Uiso 1 1 calc R . .
C5 C 0.73821(15) -0.1192(3) 0.02285(11) 0.0167(4) Uani 1 1 d U . .
C6 C 0.71664(15) 0.0756(3) 0.09045(11) 0.0177(4) Uani 1 1 d U . .
C7 C 0.61008(15) 0.1030(4) 0.12984(12) 0.0229(4) Uani 1 1 d U . .
H7 H 0.5484 -0.0091 0.1136 0.027 Uiso 1 1 calc R . .
C8 C 0.59126(16) 0.2930(4) 0.19327(12) 0.0246(4) Uani 1 1 d U . .
H8 H 0.5174 0.3073 0.2196 0.029 Uiso 1 1 calc R . .
C9 C 0.67830(16) 0.4574(4) 0.21738(12) 0.0227(4) Uani 1 1 d U . .
H9 H 0.6646 0.5862 0.2601 0.027 Uiso 1 1 calc R . .
C10 C 0.78817(15) 0.4367(3) 0.17927(11) 0.0184(4) Uani 1 1 d U . .
C11 C 0.87892(15) 0.6073(3) 0.20244(11) 0.0193(4) Uani 1 1 d U . .
H11 H 0.8647 0.7426 0.2428 0.023 Uiso 1 1 calc R . .
C12 C 0.98658(15) 0.5809(3) 0.16781(11) 0.0183(4) Uani 1 1 d U . .
H12 H 1.046 0.6983 0.1845 0.022 Uiso 1 1 calc R . .
C13 C 1.01156(14) 0.3817(3) 0.10744(11) 0.0157(4) Uani 1 1 d U . .
C14 C 0.92247(14) 0.2147(3) 0.08016(10) 0.0148(4) Uani 1 1 d U . .
C15 C 0.94478(14) 0.0163(3) 0.01735(10) 0.0145(4) Uani 1 1 d U . .
C16 C 0.85107(14) -0.1494(3) -0.01124(10) 0.0153(4) Uani 1 1 d U . .
C17 C 0.80898(14) 0.2411(3) 0.11617(10) 0.0142(4) Uani 1 1 d U . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.410(2) . ?
C1 C16 1.417(2) . ?
C1 C13 1.454(2) 3_755 ?
C2 C3 1.373(2) . ?
C2 H2 0.95 . ?
C3 C4 1.390(3) . ?
C3 H3 0.95 . ?
C4 C5 1.392(2) . ?
C4 H4 0.95 . ?
C5 C16 1.418(2) . ?
C5 C6 1.472(2) . ?
C6 C7 1.384(2) . ?
C6 C17 1.422(2) . ?
C7 C8 1.404(3) . ?
C7 H7 0.95 . ?
C8 C9 1.366(3) . ?
C8 H8 0.95 . ?
C9 C10 1.407(2) . ?
C9 H9 0.95 . ?
C10 C11 1.413(2) . ?
C10 C17 1.424(2) . ?
C11 C12 1.364(2) . ?
C11 H11 0.95 . ?
C12 C13 1.418(2) . ?
C12 H12 0.95 . ?
C13 C14 1.405(2) . ?
C13 C1 1.454(2) 3_755 ?
C14 C17 1.434(2) . ?
C14 C15 1.434(2) . ?
C15 C15 1.397(3) 3_755 ?
C15 C16 1.447(2) . ?

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 C16 119.02(16) . . ?
C2 C1 C13 120.94(16) . 3_755 ?
C16 C1 C13 120.04(15) . 3_755 ?
C3 C2 C1 120.78(16) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.30(16) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 121.09(16) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C16 119.13(16) . . ?
C4 C5 C6 121.00(16) . . ?
C16 C5 C6 119.86(15) . . ?
C7 C6 C17 118.94(16) . . ?
C7 C6 C5 122.45(16) . . ?
C17 C6 C5 118.60(15) . . ?
C6 C7 C8 121.34(17) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 120.47(17) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.25(17) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C11 121.12(17) . . ?
C9 C10 C17 119.78(16) . . ?
C11 C10 C17 119.10(15) . . ?
C12 C11 C10 121.05(16) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 121.32(16) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 119.31(15) . . ?
C14 C13 C1 119.24(15) . 3_755 ?
C12 C13 C1 121.44(15) . 3_755 ?
C13 C14 C17 119.73(15) . . ?
C13 C14 C15 120.39(15) . . ?
C17 C14 C15 119.87(15) . . ?
C15 C15 C14 120.88(19) 3_755 . ?
C15 C15 C16 119.71(19) 3_755 . ?
C14 C15 C16 119.41(15) . . ?
C1 C16 C5 119.60(15) . . ?
C1 C16 C15 119.70(15) . . ?
C5 C16 C15 120.70(15) . . ?
C6 C17 C10 119.18(15) . . ?
C6 C17 C14 121.44(15) . . ?
C10 C17 C14 119.39(15) . . ?

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
C16 C1 C2 C3 0.2(2) . . . . ?
C13 C1 C2 C3 -179.09(16) 3_755 . . . ?
C1 C2 C3 C4 -1.6(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C16 1.7(3) . . . . ?
C3 C4 C5 C6 -178.45(16) . . . . ?
C4 C5 C6 C7 4.2(3) . . . . ?
C16 C5 C6 C7 -175.95(16) . . . . ?
C4 C5 C6 C17 -175.95(16) . . . . ?
C16 C5 C6 C17 3.9(2) . . . . ?
C17 C6 C7 C8 1.1(3) . . . . ?
C5 C6 C7 C8 -179.02(16) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 C11 179.10(17) . . . . ?
C8 C9 C10 C17 -0.9(3) . . . . ?
C9 C10 C11 C12 177.52(17) . . . . ?
C17 C10 C11 C12 -2.5(2) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C14 2.6(2) . . . . ?
C11 C12 C13 C1 -177.04(16) . . . 3_755 ?
C12 C13 C14 C17 -2.5(2) . . . . ?
C1 C13 C14 C17 177.12(14) 3_755 . . . ?
C12 C13 C14 C15 178.26(15) . . . . ?
C1 C13 C14 C15 -2.1(2) 3_755 . . . ?
C13 C14 C15 C15 0.5(3) . . . 3_755 ?
C17 C14 C15 C15 -178.72(18) . . . 3_755 ?
C13 C14 C15 C16 -178.57(14) . . . . ?
C17 C14 C15 C16 2.2(2) . . . . ?
C2 C1 C16 C5 2.1(2) . . . . ?
C13 C1 C16 C5 -178.62(15) 3_755 . . . ?
C2 C1 C16 C15 -178.40(14) . . . . ?
C13 C1 C16 C15 0.9(2) 3_755 . . . ?
C4 C5 C16 C1 -3.0(2) . . . . ?
C6 C5 C16 C1 177.13(15) . . . . ?
C4 C5 C16 C15 177.49(15) . . . . ?
C6 C5 C16 C15 -2.4(2) . . . . ?
C15 C15 C16 C1 0.7(3) 3_755 . . . ?
C14 C15 C16 C1 179.80(14) . . . . ?
C15 C15 C16 C5 -179.78(18) 3_755 . . . ?
C14 C15 C16 C5 -0.7(2) . . . . ?
C7 C6 C17 C10 -2.4(2) . . . . ?
C5 C6 C17 C10 177.73(15) . . . . ?
C7 C6 C17 C14 177.44(16) . . . . ?
C5 C6 C17 C14 -2.5(2) . . . . ?
C9 C10 C17 C6 2.3(2) . . . . ?
C11 C10 C17 C6 -177.68(15) . . . . ?
C9 C10 C17 C14 -177.53(15) . . . . ?
C11 C10 C17 C14 2.5(2) . . . . ?
C13 C14 C17 C6 -179.84(15) . . . . ?
C15 C14 C17 C6 -0.6(2) . . . . ?
C13 C14 C17 C10 0.0(2) . . . . ?
C15 C14 C17 C10 179.23(15) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ch15169
_database_code_depnum_ccdc_archive 'CCDC 1401394'
_audit_update_record             
;
2015-05-17 deposited with the CCDC.
2015-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H20'
_chemical_formula_sum            'C36 H20'
_chemical_formula_weight         452.52

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'

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

_cell_length_a                   5.0661(17)
_cell_length_b                   15.948(6)
_cell_length_c                   25.586(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2067.2(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9377
_exptl_absorpt_correction_T_max  0.9984
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13633
_diffrn_reflns_av_R_equivalents  0.1562
_diffrn_reflns_av_sigmaI/netI    0.0971
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         25.04
_reflns_number_total             1795
_reflns_number_gt                884
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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 > 2sigma(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)+(0.1369P)²+0.0000P] 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         1795
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1674
_refine_ls_R_factor_gt           0.0659
_refine_ls_wR_factor_ref         0.2555
_refine_ls_wR_factor_gt          0.1682
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 1.1133(10) 0.6142(3) 0.80512(17) 0.0351(13) Uani 1 1 d . . .
H1A H 1.2374 0.6561 0.8185 0.053 Uiso 1 1 calc R . .
H1B H 0.9986 0.6400 0.7788 0.053 Uiso 1 1 calc R . .
H1C H 1.2117 0.5678 0.7892 0.053 Uiso 1 1 calc R . .
C2 C 0.9471(9) 0.5812(3) 0.84951(16) 0.0233(11) Uani 1 1 d . . .
C3 C 0.9868(8) 0.6089(3) 0.90012(15) 0.0234(12) Uani 1 1 d . . .
H3 H 1.1203 0.6493 0.9067 0.028 Uiso 1 1 calc R . .
C4 C 0.8345(8) 0.5787(3) 0.94208(15) 0.0194(11) Uani 1 1 d . . .
C5 C 0.6381(8) 0.5179(3) 0.93219(15) 0.0168(10) Uani 1 1 d . . .
C6 C 0.5975(9) 0.4879(3) 0.88008(15) 0.0204(11) Uani 1 1 d . . .
C7 C 0.7551(9) 0.5209(3) 0.84068(16) 0.0250(12) Uani 1 1 d . . .
H7 H 0.7300 0.5012 0.8060 0.030 Uiso 1 1 calc R . .
C8 C 0.4784(8) 0.4855(3) 0.97458(15) 0.0195(11) Uani 1 1 d . . .
C9 C 0.2802(9) 0.4239(3) 0.96401(15) 0.0179(11) Uani 1 1 d . . .
C10 C 0.2397(9) 0.3942(3) 0.91158(15) 0.0197(11) Uani 1 1 d . . .
C11 C 0.3964(8) 0.4248(3) 0.86979(15) 0.0194(11) Uani 1 1 d . . .
C12 C 0.3493(9) 0.3928(3) 0.81965(17) 0.0275(12) Uani 1 1 d . . .
H12 H 0.4525 0.4127 0.7912 0.033 Uiso 1 1 calc R . .
C13 C 0.1563(9) 0.3328(3) 0.81022(17) 0.0286(12) Uani 1 1 d . . .
H13 H 0.1304 0.3122 0.7758 0.034 Uiso 1 1 calc R . .
C14 C 0.0025(9) 0.3030(3) 0.85030(17) 0.0269(12) Uani 1 1 d . . .
H14 H -0.1310 0.2627 0.8435 0.032 Uiso 1 1 calc R . .
C15 C 0.0431(8) 0.3325(3) 0.90162(16) 0.0209(11) Uani 1 1 d . . .
C16 C -0.1170(9) 0.3046(3) 0.94368(16) 0.0246(12) Uani 1 1 d . . .
H16 H -0.2537 0.2652 0.9371 0.030 Uiso 1 1 calc R . .
C17 C -0.0788(9) 0.3330(3) 0.99298(16) 0.0232(11) Uani 1 1 d . . .
H17 H -0.1876 0.3125 1.0204 0.028 Uiso 1 1 calc R . .
C18 C 0.1216(8) 0.3931(3) 1.00460(15) 0.0190(11) 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 1.509(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.383(5) . ?
C2 C7 1.386(6) . ?
C3 C4 1.407(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.412(6) . ?
C4 C18 1.454(5) 5_667 ?
C5 C6 1.432(5) . ?
C5 C8 1.448(6) . ?
C6 C7 1.390(6) . ?
C6 C11 1.455(6) . ?
C7 H7 0.9500 . ?
C8 C8 1.397(8) 5_667 ?
C8 C9 1.431(6) . ?
C9 C18 1.402(6) . ?
C9 C10 1.437(5) . ?
C10 C11 1.418(6) . ?
C10 C15 1.424(6) . ?
C11 C12 1.401(6) . ?
C12 C13 1.389(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.372(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.409(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.419(6) . ?
C16 C17 1.354(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.428(6) . ?
C17 H17 0.9500 . ?
C18 C4 1.454(5) 5_667 ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 118.4(4) . . ?
C3 C2 C1 120.8(4) . . ?
C7 C2 C1 120.7(4) . . ?
C2 C3 C4 121.7(4) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 C18 121.8(4) . 5_667 ?
C5 C4 C18 119.2(4) . 5_667 ?
C4 C5 C6 119.9(4) . . ?
C4 C5 C8 120.3(4) . . ?
C6 C5 C8 119.9(4) . . ?
C7 C6 C5 117.8(4) . . ?
C7 C6 C11 122.2(4) . . ?
C5 C6 C11 120.0(4) . . ?
C2 C7 C6 123.2(4) . . ?
C2 C7 H7 118.4 . . ?
C6 C7 H7 118.4 . . ?
C8 C8 C9 120.8(5) 5_667 . ?
C8 C8 C5 119.5(5) 5_667 . ?
C9 C8 C5 119.7(4) . . ?
C18 C9 C8 120.2(4) . . ?
C18 C9 C10 119.6(4) . . ?
C8 C9 C10 120.2(4) . . ?
C11 C10 C15 119.7(4) . . ?
C11 C10 C9 120.7(4) . . ?
C15 C10 C9 119.6(4) . . ?
C12 C11 C10 118.0(4) . . ?
C12 C11 C6 122.5(4) . . ?
C10 C11 C6 119.6(4) . . ?
C13 C12 C11 122.0(4) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C14 C13 C12 120.5(4) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 119.9(4) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 121.2(4) . . ?
C14 C15 C10 119.9(4) . . ?
C16 C15 C10 118.8(4) . . ?
C17 C16 C15 121.3(4) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 121.4(4) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C9 C18 C17 119.2(4) . . ?
C9 C18 C4 120.0(4) . 5_667 ?
C17 C18 C4 120.8(4) . 5_667 ?

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
C7 C2 C3 C4 -1.2(7) . . . . ?
C1 C2 C3 C4 -179.8(4) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C2 C3 C4 C18 179.1(4) . . . 5_667 ?
C3 C4 C5 C6 0.2(6) . . . . ?
C18 C4 C5 C6 -178.3(4) 5_667 . . . ?
C3 C4 C5 C8 179.9(4) . . . . ?
C18 C4 C5 C8 1.3(6) 5_667 . . . ?
C4 C5 C6 C7 -0.5(6) . . . . ?
C8 C5 C6 C7 179.9(4) . . . . ?
C4 C5 C6 C11 179.6(4) . . . . ?
C8 C5 C6 C11 -0.1(6) . . . . ?
C3 C2 C7 C6 1.0(7) . . . . ?
C1 C2 C7 C6 179.6(4) . . . . ?
C5 C6 C7 C2 -0.2(7) . . . . ?
C11 C6 C7 C2 179.8(4) . . . . ?
C4 C5 C8 C8 -0.4(7) . . . 5_667 ?
C6 C5 C8 C8 179.2(5) . . . 5_667 ?
C4 C5 C8 C9 -179.9(4) . . . . ?
C6 C5 C8 C9 -0.3(6) . . . . ?
C8 C8 C9 C18 1.5(7) 5_667 . . . ?
C5 C8 C9 C18 -179.0(4) . . . . ?
C8 C8 C9 C10 -179.4(5) 5_667 . . . ?
C5 C8 C9 C10 0.1(6) . . . . ?
C18 C9 C10 C11 179.6(4) . . . . ?
C8 C9 C10 C11 0.5(6) . . . . ?
C18 C9 C10 C15 -1.4(6) . . . . ?
C8 C9 C10 C15 179.6(4) . . . . ?
C15 C10 C11 C12 0.4(6) . . . . ?
C9 C10 C11 C12 179.4(4) . . . . ?
C15 C10 C11 C6 -179.9(4) . . . . ?
C9 C10 C11 C6 -0.9(6) . . . . ?
C7 C6 C11 C12 0.4(7) . . . . ?
C5 C6 C11 C12 -179.6(4) . . . . ?
C7 C6 C11 C10 -179.3(4) . . . . ?
C5 C6 C11 C10 0.7(6) . . . . ?
C10 C11 C12 C13 -0.1(7) . . . . ?
C6 C11 C12 C13 -179.8(4) . . . . ?
C11 C12 C13 C14 0.4(7) . . . . ?
C12 C13 C14 C15 -1.0(7) . . . . ?
C13 C14 C15 C16 178.3(4) . . . . ?
C13 C14 C15 C10 1.3(7) . . . . ?
C11 C10 C15 C14 -1.0(6) . . . . ?
C9 C10 C15 C14 -180.0(4) . . . . ?
C11 C10 C15 C16 -178.1(4) . . . . ?
C9 C10 C15 C16 2.9(6) . . . . ?
C14 C15 C16 C17 -179.8(4) . . . . ?
C10 C15 C16 C17 -2.7(6) . . . . ?
C15 C16 C17 C18 0.9(6) . . . . ?
C8 C9 C18 C17 178.7(4) . . . . ?
C10 C9 C18 C17 -0.4(6) . . . . ?
C8 C9 C18 C4 -2.5(6) . . . 5_667 ?
C10 C9 C18 C4 178.5(4) . . . 5_667 ?
C16 C17 C18 C9 0.6(6) . . . . ?
C16 C17 C18 C4 -178.2(4) . . . 5_667 ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.177

####################################################################### 
# 
# 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_i14723
_database_code_depnum_ccdc_archive 'CCDC 1401395'
_audit_update_record             
;
2015-05-17 deposited with the CCDC.
2015-06-22 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H7 F'
_chemical_formula_sum            'C17 H7 F'
_chemical_formula_weight         230.23

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.8364(4)
_cell_length_b                   5.0807(2)
_cell_length_c                   15.5746(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.487(2)
_cell_angle_gamma                90
_cell_volume                     936.58(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    6629
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      37.73

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       niddle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.084
0 1 0 0.049
0 0 1 0.039
0 0 -1 0.148
-1 0 0 0.289
1 0 0 0.282

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_correction_T_min  0.9404
_exptl_absorpt_correction_T_max  0.982

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.022
_diffrn_reflns_number            17821
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         27.1
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             2057
_reflns_number_gt                1555
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2sigma(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)+(0.0611P)²+0.4587P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2057
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1215
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.054

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
F1 F 0.60059(7) 0.64415(18) 0.59308(6) 0.0205(3) Uani 1 1 d . . .
C1 C 0.68527(12) 0.4815(3) 0.56706(10) 0.0149(3) Uani 1 1 d . . .
C2 C 0.65915(12) 0.2932(3) 0.50638(10) 0.0146(3) Uani 1 1 d . . .
H2 H 0.5842 0.2768 0.4847 0.017 Uiso 1 1 calc R . .
C3 C 0.74417(12) 0.1275(3) 0.47737(9) 0.0123(3) Uani 1 1 d . . .
C4 C 0.72110(12) -0.0704(3) 0.41134(10) 0.0129(3) Uani 1 1 d . . .
C5 C 0.61463(13) -0.1009(3) 0.37383(10) 0.0163(3) Uani 1 1 d . . .
H5 H 0.5546 0.0104 0.3914 0.02 Uiso 1 1 calc R . .
C6 C 0.59412(13) -0.2913(3) 0.31102(10) 0.0181(4) Uani 1 1 d . . .
H6 H 0.5208 -0.3076 0.2863 0.022 Uiso 1 1 calc R . .
C7 C 0.67924(12) -0.4549(3) 0.28484(10) 0.0159(3) Uani 1 1 d . . .
H7 H 0.6646 -0.584 0.2421 0.019 Uiso 1 1 calc R . .
C8 C 0.78808(12) -0.4326(3) 0.32091(9) 0.0127(3) Uani 1 1 d . . .
C9 C 0.87631(12) -0.6035(3) 0.29591(9) 0.0138(3) Uani 1 1 d . . .
H9 H 0.8614 -0.7377 0.2549 0.017 Uiso 1 1 calc R . .
C10 C 0.98203(12) -0.5786(3) 0.32970(10) 0.0129(3) Uani 1 1 d . . .
H10 H 1.0397 -0.6957 0.3117 0.016 Uiso 1 1 calc R . .
C11 C 1.00818(12) -0.3804(3) 0.39159(9) 0.0113(3) Uani 1 1 d . . .
C12 C 0.92190(12) -0.2115(3) 0.41936(9) 0.0112(3) Uani 1 1 d . . .
C13 C 0.94512(11) -0.0139(3) 0.48306(9) 0.0108(3) Uani 1 1 d . . .
C14 C 0.85581(12) 0.1544(3) 0.51178(9) 0.0108(3) Uani 1 1 d . . .
C15 C 0.87866(12) 0.3514(3) 0.57427(9) 0.0114(3) Uani 1 1 d . . .
C16 C 0.79029(12) 0.5162(3) 0.60172(9) 0.0136(3) Uani 1 1 d . . .
H16 H 0.8037 0.6488 0.6436 0.016 Uiso 1 1 calc R . .
C17 C 0.81023(12) -0.2369(3) 0.38411(9) 0.0110(3) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.3634(16) . ?
C1 C16 1.362(2) . ?
C1 C2 1.378(2) . ?
C2 C3 1.390(2) . ?
C2 H2 0.95 . ?
C3 C14 1.428(2) . ?
C3 C4 1.462(2) . ?
C4 C5 1.393(2) . ?
C4 C17 1.420(2) . ?
C5 C6 1.395(2) . ?
C5 H5 0.95 . ?
C6 C7 1.371(2) . ?
C6 H6 0.95 . ?
C7 C8 1.406(2) . ?
C7 H7 0.95 . ?
C8 C9 1.415(2) . ?
C8 C17 1.422(2) . ?
C9 C10 1.359(2) . ?
C9 H9 0.95 . ?
C10 C11 1.426(2) . ?
C10 H10 0.95 . ?
C11 C12 1.405(2) . ?
C11 C15 1.444(2) 3_756 ?
C12 C17 1.4329(19) . ?
C12 C13 1.436(2) . ?
C13 C13 1.405(3) 3_756 ?
C13 C14 1.434(2) . ?
C14 C15 1.420(2) . ?
C15 C16 1.409(2) . ?
C15 C11 1.444(2) 3_756 ?
C16 H16 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 C1 F1 118.32(13) . . ?
C16 C1 C2 124.06(13) . . ?
F1 C1 C2 117.61(13) . . ?
C1 C2 C3 118.98(14) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C14 119.34(14) . . ?
C2 C3 C4 120.90(13) . . ?
C14 C3 C4 119.76(13) . . ?
C5 C4 C17 118.69(14) . . ?
C5 C4 C3 122.29(13) . . ?
C17 C4 C3 119.01(13) . . ?
C4 C5 C6 121.50(14) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 120.32(14) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.38(14) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 121.11(14) . . ?
C7 C8 C17 119.73(13) . . ?
C9 C8 C17 119.16(13) . . ?
C10 C9 C8 121.03(14) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 121.41(14) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C10 119.03(13) . . ?
C12 C11 C15 119.89(13) . 3_756 ?
C10 C11 C15 121.07(13) . 3_756 ?
C11 C12 C17 119.83(13) . . ?
C11 C12 C13 120.29(13) . . ?
C17 C12 C13 119.88(13) . . ?
C13 C13 C14 120.31(17) 3_756 . ?
C13 C13 C12 120.02(16) 3_756 . ?
C14 C13 C12 119.67(13) . . ?
C15 C14 C3 119.65(13) . . ?
C15 C14 C13 119.81(13) . . ?
C3 C14 C13 120.53(13) . . ?
C16 C15 C14 119.28(13) . . ?
C16 C15 C11 121.07(13) . 3_756 ?
C14 C15 C11 119.66(13) . 3_756 ?
C1 C16 C15 118.69(14) . . ?
C1 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C4 C17 C8 119.36(13) . . ?
C4 C17 C12 121.13(13) . . ?
C8 C17 C12 119.50(13) . . ?

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
C16 C1 C2 C3 -0.5(2) . . . . ?
F1 C1 C2 C3 178.82(13) . . . . ?
C1 C2 C3 C14 0.7(2) . . . . ?
C1 C2 C3 C4 -178.31(13) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
C14 C3 C4 C5 -178.27(14) . . . . ?
C2 C3 C4 C17 -179.49(13) . . . . ?
C14 C3 C4 C17 1.5(2) . . . . ?
C17 C4 C5 C6 0.4(2) . . . . ?
C3 C4 C5 C6 -179.85(14) . . . . ?
C4 C5 C6 C7 0.3(2) . . . . ?
C5 C6 C7 C8 0.0(2) . . . . ?
C6 C7 C8 C9 178.67(14) . . . . ?
C6 C7 C8 C17 -0.8(2) . . . . ?
C7 C8 C9 C10 178.77(14) . . . . ?
C17 C8 C9 C10 -1.7(2) . . . . ?
C8 C9 C10 C11 0.1(2) . . . . ?
C9 C10 C11 C12 1.4(2) . . . . ?
C9 C10 C11 C15 -178.57(14) . . . 3_756 ?
C10 C11 C12 C17 -1.3(2) . . . . ?
C15 C11 C12 C17 178.68(12) 3_756 . . . ?
C10 C11 C12 C13 178.60(13) . . . . ?
C15 C11 C12 C13 -1.5(2) 3_756 . . . ?
C11 C12 C13 C13 1.0(2) . . . 3_756 ?
C17 C12 C13 C13 -179.16(16) . . . 3_756 ?
C11 C12 C13 C14 -179.01(13) . . . . ?
C17 C12 C13 C14 0.8(2) . . . . ?
C2 C3 C14 C15 -0.7(2) . . . . ?
C4 C3 C14 C15 178.34(13) . . . . ?
C2 C3 C14 C13 179.98(13) . . . . ?
C4 C3 C14 C13 -1.0(2) . . . . ?
C13 C13 C14 C15 0.5(2) 3_756 . . . ?
C12 C13 C14 C15 -179.51(12) . . . . ?
C13 C13 C14 C3 179.82(16) 3_756 . . . ?
C12 C13 C14 C3 -0.2(2) . . . . ?
C3 C14 C15 C16 0.4(2) . . . . ?
C13 C14 C15 C16 179.75(13) . . . . ?
C3 C14 C15 C11 -179.35(13) . . . 3_756 ?
C13 C14 C15 C11 0.0(2) . . . 3_756 ?
F1 C1 C16 C15 -179.09(13) . . . . ?
C2 C1 C16 C15 0.2(2) . . . . ?
C14 C15 C16 C1 -0.2(2) . . . . ?
C11 C15 C16 C1 179.59(13) 3_756 . . . ?
C5 C4 C17 C8 -1.2(2) . . . . ?
C3 C4 C17 C8 179.00(13) . . . . ?
C5 C4 C17 C12 178.93(13) . . . . ?
C3 C4 C17 C12 -0.8(2) . . . . ?
C7 C8 C17 C4 1.5(2) . . . . ?
C9 C8 C17 C4 -178.05(13) . . . . ?
C7 C8 C17 C12 -178.70(13) . . . . ?
C9 C8 C17 C12 1.8(2) . . . . ?
C11 C12 C17 C4 179.53(13) . . . . ?
C13 C12 C17 C4 -0.3(2) . . . . ?
C11 C12 C17 C8 -0.3(2) . . . . ?
C13 C12 C17 C8 179.84(13) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ch15613
_database_code_depnum_ccdc_archive 'CCDC 1401396'
_audit_update_record             
;
2015-05-17 deposited with the CCDC.
2015-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H18'
_chemical_formula_sum            'C35 H18'
_chemical_formula_weight         438.49

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   12.403(6)
_cell_length_b                   5.099(2)
_cell_length_c                   15.999(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.079(14)
_cell_angle_gamma                90.00
_cell_volume                     1007.8(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9380
_exptl_absorpt_correction_T_max  0.9984
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4017
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_sigmaI/netI    0.0983
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         25.04
_reflns_number_total             1746
_reflns_number_gt                559
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR2004 (Giacovazzo et al, 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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 > 2sigma(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)+(0.1416P)²+0.0000P] 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         1746
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2131
_refine_ls_R_factor_gt           0.0780
_refine_ls_wR_factor_ref         0.2964
_refine_ls_wR_factor_gt          0.2024
_refine_ls_goodness_of_fit_ref   0.919
_refine_ls_restrained_S_all      0.919
_refine_ls_shift/su_max          0.002
_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 0.1207(9) -0.614(2) 1.0901(7) 0.080(4) Uani 0.50 1 d P A 1
H1A H 0.0907 -0.7194 1.0439 0.120 Uiso 0.50 1 calc PR A 1
H1B H 0.0643 -0.5120 1.1115 0.120 Uiso 0.50 1 calc PR A 1
H1C H 0.1528 -0.7266 1.1336 0.120 Uiso 0.50 1 calc PR A 1
C2 C 0.1954(6) -0.4563(11) 1.0642(4) 0.0792(19) Uani 1 1 d . A 1
H2 H 0.1378 -0.5602 1.0830 0.095 Uiso 0.50 1 d PR A 2
C3 C 0.2997(6) -0.4957(9) 1.0981(3) 0.0727(19) Uani 1 1 d . . .
H3 H 0.3143 -0.6254 1.1383 0.087 Uiso 1 1 calc R A 1
C4 C 0.3849(5) -0.3402(9) 1.0722(3) 0.0615(16) Uani 1 1 d . . .
C5 C 0.3609(5) -0.1459(9) 1.0093(3) 0.0604(16) Uani 1 1 d . . .
C6 C 0.2530(6) -0.1108(10) 0.9739(3) 0.0683(17) Uani 1 1 d . A .
C7 C 0.1719(5) -0.2682(11) 1.0026(3) 0.0803(19) Uani 1 1 d . . .
H7 H 0.1007 -0.2465 0.9800 0.096 Uiso 1 1 calc R A 1
C8 C 0.2286(5) 0.0856(10) 0.9068(3) 0.0700(18) Uani 1 1 d . . .
C9 C 0.1239(5) 0.1193(10) 0.8687(4) 0.088(2) Uani 1 1 d . A .
H9 H 0.0678 0.0145 0.8845 0.105 Uiso 1 1 calc R . .
C10 C 0.1030(6) 0.3109(12) 0.8065(4) 0.100(2) Uani 1 1 d . . .
H10 H 0.0332 0.3304 0.7809 0.120 Uiso 1 1 calc R A .
C11 C 0.1837(6) 0.4691(11) 0.7828(4) 0.088(2) Uani 1 1 d . A .
H11 H 0.1679 0.5977 0.7423 0.105 Uiso 1 1 calc R . .
C12 C 0.2904(6) 0.4397(10) 0.8190(3) 0.0669(18) Uani 1 1 d . . .
C13 C 0.3134(5) 0.2454(9) 0.8818(3) 0.0642(16) Uani 1 1 d . A .
C14 C 0.4230(5) 0.2148(9) 0.9184(3) 0.0623(17) Uani 1 1 d . . .
C15 C 0.4469(4) 0.0159(8) 0.9828(3) 0.0567(16) Uani 1 1 d . . .
C16 C 0.5057(5) 0.3774(9) 0.8926(3) 0.0636(17) Uani 1 1 d . . .
C17 C 0.4767(5) 0.5718(9) 0.8294(3) 0.0722(18) Uani 1 1 d . . .
H17 H 0.5303 0.6809 0.8117 0.087 Uiso 1 1 calc R A .
C18 C 0.3745(5) 0.6006(10) 0.7952(3) 0.0726(19) Uani 1 1 d . A .
H18 H 0.3590 0.7299 0.7549 0.087 Uiso 1 1 calc R . .


_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 1.323(11) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H2 0.3717 . ?
C2 C3 1.372(7) . ?
C2 C7 1.387(7) . ?
C2 H2 0.9600 . ?
C3 C4 1.413(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.424(6) . ?
C4 C16 1.434(7) 3_657 ?
C5 C6 1.418(7) . ?
C5 C15 1.442(7) . ?
C6 C7 1.396(7) . ?
C6 C8 1.479(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.396(7) . ?
C8 C13 1.415(7) . ?
C9 C10 1.402(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.365(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.405(7) . ?
C11 H11 0.9300 . ?
C12 C18 1.406(7) . ?
C12 C13 1.423(6) . ?
C13 C14 1.439(7) . ?
C14 C16 1.409(7) . ?
C14 C15 1.458(6) . ?
C15 C15 1.391(9) 3_657 ?
C16 C4 1.434(7) 3_657 ?
C16 C17 1.439(6) . ?
C17 C18 1.343(7) . ?
C17 H17 0.9300 . ?
C18 H18 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 H2 10.8 . . ?
H1A C1 H2 112.0 . . ?
H1B C1 H2 99.0 . . ?
H1C C1 H2 116.8 . . ?
C1 C2 C3 116.7(8) . . ?
C1 C2 C7 122.3(9) . . ?
C3 C2 C7 120.9(6) . . ?
C1 C2 H2 4.2 . . ?
C3 C2 H2 119.8 . . ?
C7 C2 H2 119.3 . . ?
C2 C3 C4 120.4(5) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 118.8(6) . . ?
C3 C4 C16 121.1(5) . 3_657 ?
C5 C4 C16 120.0(6) . 3_657 ?
C6 C5 C4 120.1(6) . . ?
C6 C5 C15 120.5(5) . . ?
C4 C5 C15 119.5(5) . . ?
C7 C6 C5 118.6(5) . . ?
C7 C6 C8 121.4(6) . . ?
C5 C6 C8 120.0(6) . . ?
C2 C7 C6 121.2(6) . . ?
C2 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C9 C8 C13 119.4(5) . . ?
C9 C8 C6 121.5(6) . . ?
C13 C8 C6 119.0(5) . . ?
C8 C9 C10 120.1(6) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 121.0(6) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.6(6) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C18 121.4(5) . . ?
C11 C12 C13 119.2(6) . . ?
C18 C12 C13 119.4(6) . . ?
C8 C13 C12 119.5(6) . . ?
C8 C13 C14 121.4(5) . . ?
C12 C13 C14 119.0(6) . . ?
C16 C14 C13 120.3(5) . . ?
C16 C14 C15 120.5(5) . . ?
C13 C14 C15 119.2(6) . . ?
C15 C15 C5 121.1(6) 3_657 . ?
C15 C15 C14 119.2(7) 3_657 . ?
C5 C15 C14 119.8(5) . . ?
C14 C16 C4 119.7(5) . 3_657 ?
C14 C16 C17 117.8(6) . . ?
C4 C16 C17 122.4(6) 3_657 . ?
C18 C17 C16 122.0(6) . . ?
C18 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C17 C18 C12 121.5(5) . . ?
C17 C18 H18 119.3 . . ?
C12 C18 H18 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 178.3(7) . . . . ?
C7 C2 C3 C4 1.5(8) . . . . ?
C2 C3 C4 C5 -1.1(7) . . . . ?
C2 C3 C4 C16 179.6(4) . . . 3_657 ?
C3 C4 C5 C6 0.1(6) . . . . ?
C16 C4 C5 C6 179.4(4) 3_657 . . . ?
C3 C4 C5 C15 179.4(4) . . . . ?
C16 C4 C5 C15 -1.3(6) 3_657 . . . ?
C4 C5 C6 C7 0.6(7) . . . . ?
C15 C5 C6 C7 -178.7(4) . . . . ?
C4 C5 C6 C8 -178.2(4) . . . . ?
C15 C5 C6 C8 2.5(6) . . . . ?
C1 C2 C7 C6 -177.4(7) . . . . ?
C3 C2 C7 C6 -0.8(8) . . . . ?
C5 C6 C7 C2 -0.2(7) . . . . ?
C8 C6 C7 C2 178.5(4) . . . . ?
C7 C6 C8 C9 -0.9(8) . . . . ?
C5 C6 C8 C9 177.9(4) . . . . ?
C7 C6 C8 C13 178.2(4) . . . . ?
C5 C6 C8 C13 -3.1(7) . . . . ?
C13 C8 C9 C10 -0.3(8) . . . . ?
C6 C8 C9 C10 178.7(5) . . . . ?
C8 C9 C10 C11 -0.8(9) . . . . ?
C9 C10 C11 C12 1.5(9) . . . . ?
C10 C11 C12 C18 179.9(5) . . . . ?
C10 C11 C12 C13 -1.1(8) . . . . ?
C9 C8 C13 C12 0.7(7) . . . . ?
C6 C8 C13 C12 -178.3(4) . . . . ?
C9 C8 C13 C14 -178.9(4) . . . . ?
C6 C8 C13 C14 2.0(7) . . . . ?
C11 C12 C13 C8 0.0(7) . . . . ?
C18 C12 C13 C8 179.0(4) . . . . ?
C11 C12 C13 C14 179.6(4) . . . . ?
C18 C12 C13 C14 -1.3(7) . . . . ?
C8 C13 C14 C16 -179.7(4) . . . . ?
C12 C13 C14 C16 0.7(6) . . . . ?
C8 C13 C14 C15 -0.3(6) . . . . ?
C12 C13 C14 C15 180.0(4) . . . . ?
C6 C5 C15 C15 179.8(5) . . . 3_657 ?
C4 C5 C15 C15 0.5(7) . . . 3_657 ?
C6 C5 C15 C14 -0.8(6) . . . . ?
C4 C5 C15 C14 179.8(4) . . . . ?
C16 C14 C15 C15 -1.6(7) . . . 3_657 ?
C13 C14 C15 C15 179.1(5) . . . 3_657 ?
C16 C14 C15 C5 179.0(4) . . . . ?
C13 C14 C15 C5 -0.3(6) . . . . ?
C13 C14 C16 C4 -178.3(4) . . . 3_657 ?
C15 C14 C16 C4 2.4(6) . . . 3_657 ?
C13 C14 C16 C17 0.0(6) . . . . ?
C15 C14 C16 C17 -179.3(4) . . . . ?
C14 C16 C17 C18 0.0(7) . . . . ?
C4 C16 C17 C18 178.2(4) 3_657 . . . ?
C16 C17 C18 C12 -0.6(8) . . . . ?
C11 C12 C18 C17 -179.6(5) . . . . ?
C13 C12 C18 C17 1.3(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.142
####################################################################### 
# 
# 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_ch15723
_database_code_depnum_ccdc_archive 'CCDC 1401397'
_audit_update_record             
;
2015-05-17 deposited with the CCDC.
2015-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H32'
_chemical_formula_sum            'C42 H32'
_chemical_formula_weight         536.68

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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                   26.659(4)
_cell_length_b                   6.1038(11)
_cell_length_c                   19.317(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.161(15)
_cell_angle_gamma                90.00
_cell_volume                     2745.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            orange-red
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9519
_exptl_absorpt_correction_T_max  0.9993
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8616
_diffrn_reflns_av_R_equivalents  0.1070
_diffrn_reflns_av_sigmaI/netI    0.1454
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         25.06
_reflns_number_total             2427
_reflns_number_gt                902
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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 > 2sigma(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)+(0.1188P)²+0.0000P] 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         2427
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2130
_refine_ls_R_factor_gt           0.0680
_refine_ls_wR_factor_ref         0.2590
_refine_ls_wR_factor_gt          0.1624
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_restrained_S_all      0.952
_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 0.0602(2) 0.4832(8) 0.1649(3) 0.0405(14) Uani 1 1 d . . .
C2 C 0.0828(3) 0.5435(15) 0.1090(3) 0.125(4) Uani 1 1 d . . .
H2A H 0.1174 0.4575 0.1223 0.188 Uiso 1 1 calc R . .
H2B H 0.0923 0.6999 0.1143 0.188 Uiso 1 1 calc R . .
H2C H 0.0534 0.5122 0.0543 0.188 Uiso 1 1 calc R . .
C3 C 0.0075(3) 0.6121(11) 0.1447(3) 0.091(3) Uani 1 1 d . . .
H3A H -0.0215 0.5824 0.0896 0.137 Uiso 1 1 calc R . .
H3B H 0.0169 0.7686 0.1509 0.137 Uiso 1 1 calc R . .
H3C H -0.0075 0.5702 0.1801 0.137 Uiso 1 1 calc R . .
C4 C 0.0440(3) 0.2439(10) 0.1502(3) 0.108(3) Uani 1 1 d . . .
H4A H 0.0783 0.1566 0.1629 0.161 Uiso 1 1 calc R . .
H4B H 0.0155 0.2226 0.0943 0.161 Uiso 1 1 calc R . .
H4C H 0.0278 0.1973 0.1837 0.161 Uiso 1 1 calc R . .
C5 C 0.10524(19) 0.5313(8) 0.2517(3) 0.0366(14) Uani 1 1 d . . .
C6 C 0.1106(2) 0.3972(8) 0.3132(3) 0.0374(14) Uani 1 1 d . . .
H6 H 0.0859 0.2741 0.3007 0.045 Uiso 1 1 calc R . .
C7 C 0.1506(2) 0.4358(8) 0.3923(3) 0.0321(13) Uani 1 1 d . . .
C8 C 0.18821(19) 0.6169(7) 0.4103(3) 0.0283(12) Uani 1 1 d . . .
C9 C 0.18292(19) 0.7584(8) 0.3489(3) 0.0305(13) Uani 1 1 d . . .
C10 C 0.1412(2) 0.7096(8) 0.2699(3) 0.0377(14) Uani 1 1 d . . .
H10 H 0.1379 0.8021 0.2283 0.045 Uiso 1 1 calc R . .
C11 C 0.23151(19) 0.6600(7) 0.4915(3) 0.0284(12) Uani 1 1 d . . .
C12 C 0.23641(19) 0.5180(7) 0.5539(3) 0.0282(12) Uani 1 1 d . . .
C13 C 0.19921(19) 0.3318(7) 0.5345(2) 0.0276(12) Uani 1 1 d . . .
C14 C 0.1563(2) 0.2882(7) 0.4555(3) 0.0304(12) Uani 1 1 d . . .
C15 C 0.1214(2) 0.1053(8) 0.4413(3) 0.0396(14) Uani 1 1 d . . .
H15 H 0.0921 0.0764 0.3886 0.047 Uiso 1 1 calc R . .
C16 C 0.1280(2) -0.0365(8) 0.5014(3) 0.0411(14) Uani 1 1 d . . .
H16 H 0.1034 -0.1599 0.4895 0.049 Uiso 1 1 calc R . .
C17 C 0.1698(2) 0.0021(8) 0.5775(3) 0.0411(14) Uani 1 1 d . . .
H17 H 0.1747 -0.0968 0.6183 0.049 Uiso 1 1 calc R . .
C18 C 0.2058(2) 0.1874(7) 0.5962(3) 0.0325(13) Uani 1 1 d . . .
C19 C 0.2496(2) 0.2293(9) 0.6749(3) 0.0374(14) Uani 1 1 d . . .
H19 H 0.2544 0.1331 0.7163 0.045 Uiso 1 1 calc R . .
C20 C 0.2843(2) 0.4039(8) 0.6914(3) 0.0333(13) Uani 1 1 d . . .
H20 H 0.3135 0.4269 0.7446 0.040 Uiso 1 1 calc R . .
C21 C 0.2791(2) 0.5559(8) 0.6321(3) 0.0313(12) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.485(7) . ?
C1 C4 1.510(7) . ?
C1 C2 1.517(8) . ?
C1 C5 1.541(6) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C10 1.378(6) . ?
C5 C6 1.392(6) . ?
C6 C7 1.393(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.416(6) . ?
C7 C14 1.465(6) . ?
C8 C9 1.418(6) . ?
C8 C11 1.448(6) . ?
C9 C10 1.415(6) . ?
C9 C21 1.443(6) 7_566 ?
C10 H10 0.9500 . ?
C11 C11 1.404(8) 7_566 ?
C11 C12 1.439(6) . ?
C12 C21 1.398(6) . ?
C12 C13 1.433(6) . ?
C13 C14 1.417(6) . ?
C13 C18 1.424(6) . ?
C14 C15 1.392(6) . ?
C15 C16 1.390(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.365(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.412(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.417(6) . ?
C19 C20 1.345(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.426(6) . ?
C20 H20 0.9500 . ?
C21 C9 1.443(6) 7_566 ?

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
C3 C1 C4 108.4(5) . . ?
C3 C1 C2 109.7(5) . . ?
C4 C1 C2 106.0(6) . . ?
C3 C1 C5 108.7(4) . . ?
C4 C1 C5 112.9(4) . . ?
C2 C1 C5 111.0(5) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C5 C6 118.5(4) . . ?
C10 C5 C1 120.3(5) . . ?
C6 C5 C1 121.2(5) . . ?
C7 C6 C5 122.8(5) . . ?
C7 C6 H6 118.6 . . ?
C5 C6 H6 118.6 . . ?
C6 C7 C8 118.3(5) . . ?
C6 C7 C14 121.5(4) . . ?
C8 C7 C14 120.1(4) . . ?
C7 C8 C9 119.9(4) . . ?
C7 C8 C11 120.2(4) . . ?
C9 C8 C11 119.8(4) . . ?
C10 C9 C8 118.7(4) . . ?
C10 C9 C21 121.7(5) . 7_566 ?
C8 C9 C21 119.6(4) . 7_566 ?
C5 C10 C9 121.7(5) . . ?
C5 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C11 C11 C12 120.6(5) 7_566 . ?
C11 C11 C8 119.6(5) 7_566 . ?
C12 C11 C8 119.8(4) . . ?
C21 C12 C13 120.6(4) . . ?
C21 C12 C11 120.0(4) . . ?
C13 C12 C11 119.3(4) . . ?
C14 C13 C18 119.4(4) . . ?
C14 C13 C12 121.6(4) . . ?
C18 C13 C12 119.0(4) . . ?
C15 C14 C13 118.3(5) . . ?
C15 C14 C7 122.8(4) . . ?
C13 C14 C7 118.9(4) . . ?
C16 C15 C14 122.3(5) . . ?
C16 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C17 C16 C15 119.8(5) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.7(5) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C19 121.4(5) . . ?
C17 C18 C13 119.4(4) . . ?
C19 C18 C13 119.2(4) . . ?
C20 C19 C18 120.6(5) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 122.6(4) . . ?
C19 C20 H20 118.7 . . ?
C21 C20 H20 118.7 . . ?
C12 C21 C20 118.0(5) . . ?
C12 C21 C9 120.4(4) . 7_566 ?
C20 C21 C9 121.6(4) . 7_566 ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.261
