# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_origi27m
_database_code_depnum_ccdc_archive 'CCDC 1901231'
loop_
_audit_author_name
_audit_author_address
'benny bogoslavsky'
;The Hebrew University of Jerusalem
Israel
;
_audit_update_record             
;
2019-03-05 deposited with the CCDC.	2019-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H18'
_chemical_formula_sum            'C26 H18'
_chemical_formula_weight         330.40

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

_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                   5.859(1)
_cell_length_b                   22.260(5)
_cell_length_c                   6.880(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.237(3)
_cell_angle_gamma                90.00
_cell_volume                     847.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(1)
_cell_measurement_reflns_used    4162
_cell_measurement_theta_min      3.267
_cell_measurement_theta_max      27.988

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9636
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_process_details   'Bruker SADABS V2.05'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(1)
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9352
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         27.99
_reflns_number_total             2010
_reflns_number_gt                1956
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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 > 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)+(0.0241P)²+0.7953P] 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         2010
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0875
_refine_ls_wR_factor_ref         0.1561
_refine_ls_wR_factor_gt          0.1549
_refine_ls_goodness_of_fit_ref   1.334
_refine_ls_restrained_S_all      1.334
_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 0.7570(4) 0.10061(10) 0.6026(3) 0.0294(5) Uani 1 1 d . . .
C2 C 0.5268(4) 0.11259(11) 0.4797(4) 0.0338(5) Uani 1 1 d . . .
H2 H 0.4461 0.1452 0.5110 0.041 Uiso 1 1 calc R . .
C3 C 0.4070(4) 0.07699(11) 0.3064(4) 0.0347(5) Uani 1 1 d . . .
H3 H 0.2492 0.0862 0.2263 0.042 Uiso 1 1 calc R . .
C4 C 0.5205(4) 0.02955(11) 0.2564(4) 0.0323(5) Uani 1 1 d . . .
H4 H 0.4391 0.0060 0.1430 0.039 Uiso 1 1 calc R . .
C5 C 0.7634(4) 0.01515(10) 0.3754(3) 0.0281(5) Uani 1 1 d . . .
C6 C 0.8847(4) 0.05062(10) 0.5535(3) 0.0269(5) Uani 1 1 d . . .
C7 C 1.1179(4) 0.03392(10) 0.6735(3) 0.0288(5) Uani 1 1 d . . .
H7 H 1.1972 0.0563 0.7904 0.035 Uiso 1 1 calc R . .
C8 C 0.8693(4) 0.13847(10) 0.7895(3) 0.0290(5) Uani 1 1 d . . .
C9 C 1.0726(5) 0.17362(11) 0.8126(4) 0.0362(6) Uani 1 1 d . . .
H9 H 1.1476 0.1723 0.7128 0.043 Uiso 1 1 calc R . .
C10 C 1.1646(5) 0.21036(12) 0.9817(4) 0.0425(6) Uani 1 1 d . . .
H10 H 1.3000 0.2338 0.9942 0.051 Uiso 1 1 calc R . .
C11 C 1.0568(5) 0.21263(12) 1.1334(4) 0.0433(6) Uani 1 1 d . . .
H11 H 1.1189 0.2376 1.2472 0.052 Uiso 1 1 calc R . .
C12 C 0.8567(5) 0.17750(12) 1.1135(4) 0.0419(6) Uani 1 1 d . . .
H12 H 0.7840 0.1784 1.2150 0.050 Uiso 1 1 calc R . .
C13 C 0.7637(5) 0.14091(11) 0.9433(4) 0.0360(6) Uani 1 1 d . . .
H13 H 0.6282 0.1175 0.9313 0.043 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 1.362(3) . ?
C1 C6 1.442(3) . ?
C1 C8 1.496(3) . ?
C2 C3 1.411(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.352(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.425(3) . ?
C4 H4 0.9300 . ?
C5 C7 1.394(3) 3_756 ?
C5 C6 1.434(3) . ?
C6 C7 1.394(3) . ?
C7 C5 1.394(3) 3_756 ?
C7 H7 0.9300 . ?
C8 C9 1.390(3) . ?
C8 C13 1.391(3) . ?
C9 C10 1.378(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.387(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9300 . ?
C13 H13 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 119.3(2) . . ?
C2 C1 C8 119.2(2) . . ?
C6 C1 C8 121.4(2) . . ?
C1 C2 C3 122.0(2) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C7 C5 C4 121.4(2) 3_756 . ?
C7 C5 C6 119.4(2) 3_756 . ?
C4 C5 C6 119.1(2) . . ?
C7 C6 C5 118.2(2) . . ?
C7 C6 C1 123.4(2) . . ?
C5 C6 C1 118.4(2) . . ?
C6 C7 C5 122.4(2) . 3_756 ?
C6 C7 H7 118.8 . . ?
C5 C7 H7 118.8 3_756 . ?
C9 C8 C13 118.0(2) . . ?
C9 C8 C1 122.2(2) . . ?
C13 C8 C1 119.7(2) . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.6(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 119.2(2) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 121.1(2) . . ?
C12 C13 H13 119.4 . . ?
C8 C13 H13 119.4 . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.99
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.048



