# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1481132'
_audit_update_record             
;
2016-05-20 deposited with the CCDC.
2017-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 'C24 H16'
;
_chemical_name_common            'C24 H16'
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H16'
_chemical_formula_sum            'C24 H16'
_chemical_formula_weight         304.37

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)

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

_cell_length_a                   6.1567(7)
_cell_length_b                   7.2515(8)
_cell_length_c                   16.757(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.203(5)
_cell_angle_gamma                90.00
_cell_volume                     745.03(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    347
_cell_measurement_theta_min      2.5090
_cell_measurement_theta_max      27.0402

_exptl_crystal_description       'thin plate'
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.002
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 D8 VENTURE PHOTON'
_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            4292
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_av_sigmaI/netI    0.0797
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         23.27
_reflns_number_total             1778
_reflns_number_gt                1350
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.7500P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_number_reflns         1778
_refine_ls_number_parameters     218
_refine_ls_number_restraints     115
_refine_ls_R_factor_all          0.2486
_refine_ls_R_factor_gt           0.2288
_refine_ls_wR_factor_ref         0.6542
_refine_ls_wR_factor_gt          0.6281
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.310
_refine_ls_shift/su_mean         0.067

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 -1.489(2) -0.414(2) -1.4796(8) 0.030(4) Uani 1 1 d U . .
H1A H -1.6176 -0.4490 -1.5094 0.036 Uiso 1 1 calc R . .
C2 C -1.314(4) -0.395(4) -1.5162(12) 0.070(6) Uani 1 1 d U . .
H2A H -1.3082 -0.4280 -1.5696 0.084 Uiso 1 1 calc R . .
C3 C -1.113(2) -0.315(2) -1.4650(9) 0.031(4) Uani 1 1 d U . .
H3A H -0.9774 -0.3034 -1.4850 0.037 Uiso 1 1 calc R . .
C4 C -1.146(2) -0.265(2) -1.3915(9) 0.034(4) Uani 1 1 d U . .
H4A H -1.0293 -0.2134 -1.3600 0.041 Uiso 1 1 calc R . .
C5 C -1.351(2) -0.283(3) -1.3565(8) 0.035(4) Uani 1 1 d U . .
C6 C -1.493(2) -0.389(3) -1.4125(8) 0.031(4) Uani 1 1 d U . .
H6A H -1.6084 -0.4460 -1.3900 0.037 Uiso 1 1 calc R . .
C7 C -1.378(3) -0.255(3) -1.2766(10) 0.050(5) Uani 1 1 d U . .
C8 C -1.220(3) -0.287(3) -1.2109(10) 0.042(5) Uani 1 1 d . . .
H8A H -1.0850 -0.3322 -1.2229 0.050 Uiso 1 1 calc R . .
C9 C -1.247(3) -0.260(3) -1.1319(11) 0.056(5) Uani 1 1 d U . .
C10 C -1.465(3) -0.173(3) -1.1111(9) 0.036(4) Uani 1 1 d U . .
C11 C -1.609(3) -0.145(3) -1.1742(10) 0.047(5) Uani 1 1 d . . .
H11A H -1.7424 -0.0943 -1.1638 0.057 Uiso 1 1 calc R . .
C12 C -1.582(3) -0.180(3) -1.2492(11) 0.052(5) Uani 1 1 d U . .
H12A H -1.6984 -0.1576 -1.2874 0.063 Uiso 1 1 calc R . .
C13 C -1.092(3) -0.294(3) -1.0705(10) 0.043(5) Uani 1 1 d U . .
H13A H -0.9597 -0.3443 -1.0824 0.051 Uiso 1 1 calc R . .
C14 C -1.121(3) -0.256(3) -0.9897(11) 0.047(5) Uani 1 1 d . . .
C15 C -1.331(2) -0.177(2) -0.9684(10) 0.033(4) Uani 1 1 d . . .
C16 C -1.481(4) -0.135(3) -1.0333(11) 0.062(6) Uani 1 1 d U . .
H16A H -1.6069 -0.0734 -1.0214 0.075 Uiso 1 1 calc R . .
C17 C -0.963(3) -0.288(3) -0.9256(11) 0.049(5) Uani 1 1 d U . .
H17A H -0.8281 -0.3348 -0.9369 0.059 Uiso 1 1 calc R . .
C18 C -0.997(3) -0.253(3) -0.8449(11) 0.048(5) Uani 1 1 d U . .
C19 C -1.199(3) -0.172(3) -0.8268(10) 0.041(4) Uani 1 1 d U . .
C20 C -1.350(3) -0.140(3) -0.8900(10) 0.052(5) Uani 1 1 d U . .
H20A H -1.4803 -0.0856 -0.8781 0.062 Uiso 1 1 calc R . .
C21 C -0.821(2) -0.301(2) -0.7842(9) 0.028(4) Uani 1 1 d U . .
H21A H -0.6906 -0.3507 -0.7983 0.033 Uiso 1 1 calc R . .
C22 C -0.852(5) -0.272(5) -0.7106(16) 0.098(9) Uani 1 1 d U . .
H22A H -0.7424 -0.3008 -0.6706 0.118 Uiso 1 1 calc R . .
C23 C -1.062(3) -0.192(2) -0.6883(10) 0.038(4) Uani 1 1 d . . .
H23A H -1.0844 -0.1726 -0.6347 0.045 Uiso 1 1 calc R . .
C24 C -1.219(4) -0.147(3) -0.7469(10) 0.051(5) Uani 1 1 d U . .
H24A H -1.3482 -0.0959 -0.7321 0.062 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.027(5) 0.026(6) 0.037(5) 0.002(4) 0.006(4) -0.006(4)
C2 0.079(10) 0.063(10) 0.067(9) 0.006(8) -0.001(7) -0.011(9)
C3 0.031(6) 0.021(7) 0.042(7) 0.008(6) 0.012(5) -0.003(6)
C4 0.033(6) 0.013(7) 0.056(8) 0.017(6) 0.003(5) -0.006(6)
C5 0.034(6) 0.039(8) 0.034(7) 0.013(6) 0.017(5) 0.013(6)
C6 0.026(5) 0.026(6) 0.040(5) 0.010(4) 0.007(4) -0.013(4)
C7 0.056(8) 0.041(9) 0.051(8) -0.005(7) -0.006(6) 0.004(7)
C8 0.031(8) 0.032(12) 0.062(11) -0.016(9) 0.009(7) -0.011(8)
C9 0.057(8) 0.050(9) 0.061(9) -0.003(7) 0.005(7) -0.005(8)
C10 0.037(7) 0.025(8) 0.047(8) -0.006(6) 0.014(6) 0.015(6)
C11 0.044(10) 0.049(13) 0.050(11) -0.021(9) 0.011(8) -0.036(9)
C12 0.067(9) 0.031(8) 0.058(9) 0.007(7) 0.000(7) -0.010(7)
C13 0.046(7) 0.032(8) 0.051(8) 0.003(7) 0.002(6) 0.003(7)
C14 0.035(9) 0.047(13) 0.061(11) -0.024(9) 0.015(7) 0.005(9)
C15 0.011(7) 0.010(9) 0.079(12) -0.006(8) 0.015(7) 0.003(7)
C16 0.065(9) 0.052(10) 0.067(9) 0.005(7) -0.004(7) 0.000(8)
C17 0.042(7) 0.045(9) 0.063(8) -0.011(7) 0.017(6) 0.000(7)
C18 0.052(8) 0.035(9) 0.057(8) 0.009(7) 0.001(6) -0.009(7)
C19 0.025(6) 0.045(9) 0.052(8) 0.004(7) 0.005(6) -0.013(6)
C20 0.047(8) 0.050(10) 0.059(9) 0.000(7) 0.002(7) -0.016(7)
C21 0.028(6) 0.012(7) 0.044(7) 0.001(6) 0.008(5) 0.013(6)
C22 0.096(11) 0.099(13) 0.098(11) 0.005(9) 0.001(8) -0.002(9)
C23 0.038(9) 0.013(10) 0.065(11) 0.006(8) 0.018(7) 0.000(8)
C24 0.064(9) 0.035(9) 0.055(8) 0.004(7) 0.002(7) -0.004(7)

_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 1.142(17) . ?
C1 C2 1.30(3) . ?
C2 C3 1.55(3) . ?
C3 C4 1.32(2) . ?
C4 C5 1.44(2) . ?
C5 C6 1.45(2) . ?
C5 C7 1.38(2) . ?
C7 C8 1.42(2) . ?
C7 C12 1.48(3) . ?
C8 C9 1.36(2) . ?
C9 C13 1.36(3) . ?
C9 C10 1.55(3) . ?
C10 C11 1.33(2) . ?
C10 C16 1.34(2) . ?
C11 C12 1.31(2) . ?
C13 C14 1.41(2) . ?
C14 C17 1.40(3) . ?
C14 C15 1.48(2) . ?
C15 C20 1.36(2) . ?
C15 C16 1.40(2) . ?
C17 C18 1.41(3) . ?
C18 C21 1.46(2) . ?
C18 C19 1.43(3) . ?
C19 C20 1.37(2) . ?
C19 C24 1.37(2) . ?
C21 C22 1.28(3) . ?
C22 C23 1.50(4) . ?
C23 C24 1.36(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
C6 C1 C2 122.8(16) . . ?
C1 C2 C3 115.8(16) . . ?
C4 C3 C2 115.9(15) . . ?
C3 C4 C5 124.7(14) . . ?
C6 C5 C4 106.6(13) . . ?
C6 C5 C7 126.1(14) . . ?
C4 C5 C7 124.6(15) . . ?
C1 C6 C5 131.2(14) . . ?
C8 C7 C5 126.4(18) . . ?
C8 C7 C12 111.2(16) . . ?
C5 C7 C12 122.4(15) . . ?
C7 C8 C9 126.4(19) . . ?
C13 C9 C8 125(2) . . ?
C13 C9 C10 117.7(18) . . ?
C8 C9 C10 117.5(17) . . ?
C11 C10 C16 129.4(19) . . ?
C11 C10 C9 114.3(15) . . ?
C16 C10 C9 116.3(17) . . ?
C12 C11 C10 126.9(19) . . ?
C11 C12 C7 123.7(17) . . ?
C9 C13 C14 123.3(19) . . ?
C13 C14 C17 124.2(17) . . ?
C13 C14 C15 119.8(16) . . ?
C17 C14 C15 116.1(16) . . ?
C20 C15 C16 126.6(19) . . ?
C20 C15 C14 117.8(15) . . ?
C16 C15 C14 115.3(17) . . ?
C10 C16 C15 127(2) . . ?
C18 C17 C14 123.4(17) . . ?
C17 C18 C21 117.5(17) . . ?
C17 C18 C19 119.0(15) . . ?
C21 C18 C19 123.6(16) . . ?
C20 C19 C24 128.2(19) . . ?
C20 C19 C18 116.8(17) . . ?
C24 C19 C18 114.9(15) . . ?
C15 C20 C19 127(2) . . ?
C22 C21 C18 117.8(19) . . ?
C21 C22 C23 121(2) . . ?
C24 C23 C22 119.2(19) . . ?
C19 C24 C23 123.7(19) . . ?

_diffrn_measured_fraction_theta_max 0.913
_diffrn_reflns_theta_full        23.27
_diffrn_measured_fraction_theta_full 0.913
_refine_diff_density_max         1.096
_refine_diff_density_min         -0.699
_refine_diff_density_rms         0.207
