# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1036772'
_audit_update_record             
;
2015-04-16 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;
_chemical_name_systematic        1,2-bis(9-anthryl)acetylene
_chemical_name_common            1beta
_chemical_formula_moiety         'C30 H18'
_chemical_formula_sum            'C30 H18'
_chemical_formula_iupac          'C30 H18'
_chemical_formula_weight         378.44

_chemical_melting_point          'not determined'

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_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                   12.8185(10)
_cell_length_b                   14.0656(11)
_cell_length_c                   11.5956(9)
_cell_angle_alpha                90
_cell_angle_beta                 112.1330(10)
_cell_angle_gamma                90
_cell_volume                     1936.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2441
_cell_measurement_theta_min      2.2446
_cell_measurement_theta_max      27.0227
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792

_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3660

_diffrn_reflns_number            8566
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         27.12
_diffrn_reflns_theta_full        27.12
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             2147
_reflns_number_gt                1636
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1530
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_number_reflns         2147
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0941P)²+0.2717P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.179
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.33263(9) 0.36107(8) 0.64260(10) 0.0310(3) Uani d . . . 1 . .
C C2 0.28284(9) 0.43374(9) 0.55494(10) 0.0332(3) Uani d . . . 1 . .
C C3 0.34715(11) 0.50577(9) 0.52597(11) 0.0409(3) Uani d . . . 1 . .
H H3 0.4252 0.5051 0.5646 0.049 Uiso calc U . R 1 . .
C C4 0.29590(13) 0.57574(11) 0.44239(13) 0.0513(4) Uani d . . . 1 . .
H H4 0.3393 0.6219 0.4241 0.062 Uiso calc U . R 1 . .
C C5 0.17662(14) 0.57868(12) 0.38304(13) 0.0576(4) Uani d . . . 1 . .
H H5 0.1423 0.6275 0.3277 0.069 Uiso calc U . R 1 . .
C C6 0.11289(12) 0.51058(11) 0.40689(12) 0.0504(4) Uani d . . . 1 . .
H H6 0.035 0.5132 0.367 0.06 Uiso calc U . R 1 . .
C C7 0.16232(10) 0.43498(9) 0.49170(11) 0.0384(3) Uani d . . . 1 . .
C C8 0.09799(10) 0.36361(10) 0.51610(11) 0.0416(3) Uani d . . . 1 . .
H H8 0.0201 0.3656 0.476 0.05 Uiso calc U . R 1 . .
C C9 0.14645(10) 0.28944(9) 0.59840(11) 0.0378(3) Uani d . . . 1 . .
C C10 0.08112(11) 0.21557(11) 0.62361(13) 0.0499(4) Uani d . . . 1 . .
H H10 0.0032 0.2162 0.5833 0.06 Uiso calc U . R 1 . .
C C11 0.13066(13) 0.14504(11) 0.70485(14) 0.0555(4) Uani d . . . 1 . .
H H11 0.0866 0.0979 0.7201 0.067 Uiso calc U . R 1 . .
C C12 0.24891(13) 0.14225(11) 0.76680(13) 0.0507(4) Uani d . . . 1 . .
H H12 0.2822 0.0929 0.8218 0.061 Uiso calc U . R 1 . .
C C13 0.31445(11) 0.21114(9) 0.74657(11) 0.0415(3) Uani d . . . 1 . .
H H13 0.3922 0.2083 0.7883 0.05 Uiso calc U . R 1 . .
C C14 0.26642(9) 0.28732(8) 0.66292(10) 0.0330(3) Uani d . . . 1 . .
C C15 0.45140(9) 0.36287(8) 0.71589(10) 0.0331(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.4129(16) ?
C1 C14 . 1.4152(16) ?
C1 C15 . 1.4373(14) ?
C2 C3 . 1.4239(18) ?
C2 C7 . 1.4391(16) ?
C3 C4 . 1.3638(19) ?
C3 H3 . 0.93 ?
C4 C5 . 1.421(2) ?
C4 H4 . 0.93 ?
C5 C6 . 1.353(2) ?
C5 H5 . 0.93 ?
C6 C7 . 1.4247(19) ?
C6 H6 . 0.93 ?
C7 C8 . 1.3941(19) ?
C8 C9 . 1.3922(19) ?
C8 H8 . 0.93 ?
C9 C10 . 1.4320(18) ?
C9 C14 . 1.4348(16) ?
C10 C11 . 1.351(2) ?
C10 H10 . 0.93 ?
C11 C12 . 1.412(2) ?
C11 H11 . 0.93 ?
C12 C13 . 1.3595(19) ?
C12 H12 . 0.93 ?
C13 C14 . 1.4205(17) ?
C13 H13 . 0.93 ?
C15 C15 2_656 1.198(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C14 . . 120.89(10) ?
C2 C1 C15 . . 120.22(10) ?
C14 C1 C15 . . 118.85(10) ?
C1 C2 C3 . . 122.66(10) ?
C1 C2 C7 . . 118.86(11) ?
C3 C2 C7 . . 118.48(11) ?
C4 C3 C2 . . 120.96(12) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C3 C4 C5 . . 120.49(14) ?
C3 C4 H4 . . 119.8 ?
C5 C4 H4 . . 119.8 ?
C6 C5 C4 . . 120.17(13) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C5 C6 C7 . . 121.57(12) ?
C5 C6 H6 . . 119.2 ?
C7 C6 H6 . . 119.2 ?
C8 C7 C6 . . 122.30(11) ?
C8 C7 C2 . . 119.43(11) ?
C6 C7 C2 . . 118.27(12) ?
C9 C8 C7 . . 122.24(10) ?
C9 C8 H8 . . 118.9 ?
C7 C8 H8 . . 118.9 ?
C8 C9 C10 . . 122.65(11) ?
C8 C9 C14 . . 119.13(11) ?
C10 C9 C14 . . 118.21(12) ?
C11 C10 C9 . . 121.20(12) ?
C11 C10 H10 . . 119.4 ?
C9 C10 H10 . . 119.4 ?
C10 C11 C12 . . 120.50(13) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C13 C12 C11 . . 120.47(14) ?
C13 C12 H12 . . 119.8 ?
C11 C12 H12 . . 119.8 ?
C12 C13 C14 . . 121.22(12) ?
C12 C13 H13 . . 119.4 ?
C14 C13 H13 . . 119.4 ?
C1 C14 C13 . . 122.26(10) ?
C1 C14 C9 . . 119.35(11) ?
C13 C14 C9 . . 118.39(11) ?
C15 C15 C1 2_656 . 175.39(16) ?

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1059941'
_audit_update_record             
;
2015-04-16 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;
_chemical_name_systematic        1,2-bis(9-anthryl)acetylene
_chemical_name_common            1aplha
_chemical_formula_moiety         'C30 H18'
_chemical_formula_sum            'C30 H18'
_chemical_formula_iupac          'C30 H18'
_chemical_formula_weight         378.44

_chemical_melting_point          'not determined'

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   12.388(3)
_cell_length_b                   5.0693(11)
_cell_length_c                   15.112(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.269(3)
_cell_angle_gamma                90
_cell_volume                     946.4(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1134
_cell_measurement_theta_min      2.7031
_cell_measurement_theta_max      25.1048
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396

_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3660

_diffrn_reflns_number            7288
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         26.22
_diffrn_reflns_theta_full        26.22
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             1907
_reflns_number_gt                1217
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_gt          0.1340
_refine_ls_wR_factor_ref         0.1595
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_number_reflns         1907
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0909P)²+0.0020P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.134
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.93427(13) 0.2087(3) 0.42073(10) 0.0357(4) Uani d . . . 1 . .
C C2 0.98884(13) 0.1202(3) 0.34739(10) 0.0374(4) Uani d . . . 1 . .
C C3 1.08728(15) 0.2342(3) 0.32376(11) 0.0454(5) Uani d . . . 1 . .
H H3 1.119 0.3735 0.3588 0.054 Uiso calc U . R 1 . .
C C4 1.13716(16) 0.1481(4) 0.25205(12) 0.0517(5) Uani d . . . 1 . .
H H4 1.2023 0.23 0.2371 0.062 Uiso calc U . R 1 . .
C C5 1.09301(16) -0.0624(3) 0.19941(12) 0.0518(5) Uani d . . . 1 . .
H H5 1.129 -0.122 0.1498 0.062 Uiso calc U . R 1 . .
C C6 0.99996(15) -0.1784(3) 0.21969(12) 0.0473(5) Uani d . . . 1 . .
H H6 0.9713 -0.3202 0.1842 0.057 Uiso calc U . R 1 . .
C C7 0.94383(14) -0.0919(3) 0.29346(11) 0.0400(4) Uani d . . . 1 . .
C C8 0.84657(14) -0.2055(3) 0.31371(11) 0.0432(5) Uani d . . . 1 . .
H H8 0.8176 -0.3469 0.2781 0.052 Uiso calc U . R 1 . .
C C9 0.79032(14) -0.1184(3) 0.38450(11) 0.0404(4) Uani d . . . 1 . .
C C10 0.68973(15) -0.2327(3) 0.40382(12) 0.0481(5) Uani d . . . 1 . .
H H10 0.6604 -0.3729 0.3679 0.058 Uiso calc U . R 1 . .
C C11 0.63535(15) -0.1458(4) 0.47220(12) 0.0528(5) Uani d . . . 1 . .
H H11 0.5683 -0.2246 0.4839 0.063 Uiso calc U . R 1 . .
C C12 0.67784(16) 0.0625(3) 0.52657(12) 0.0526(5) Uani d . . . 1 . .
H H12 0.639 0.1232 0.5745 0.063 Uiso calc U . R 1 . .
C C13 0.77396(14) 0.1764(3) 0.51072(11) 0.0459(5) Uani d . . . 1 . .
H H13 0.8014 0.3152 0.5482 0.055 Uiso calc U . R 1 . .
C C14 0.83413(13) 0.0926(3) 0.43947(10) 0.0378(4) Uani d . . . 1 . .
C C15 0.98034(13) 0.4141(3) 0.47657(10) 0.0386(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.414(2) ?
C1 C14 . 1.420(2) ?
C1 C15 . 1.432(2) ?
C2 C3 . 1.419(2) ?
C2 C7 . 1.436(2) ?
C3 C4 . 1.359(2) ?
C4 C5 . 1.416(2) ?
C5 C6 . 1.349(2) ?
C6 C7 . 1.426(2) ?
C7 C8 . 1.390(2) ?
C8 C9 . 1.391(2) ?
C9 C10 . 1.424(2) ?
C9 C14 . 1.436(2) ?
C10 C11 . 1.349(3) ?
C11 C12 . 1.415(2) ?
C12 C13 . 1.361(2) ?
C13 C14 . 1.419(2) ?
C15 C15 3_766 1.202(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C14 . . 120.04(14) ?
C2 C1 C15 . . 120.00(15) ?
C14 C1 C15 . . 119.96(15) ?
C1 C2 C3 . . 122.57(15) ?
C1 C2 C7 . . 119.62(16) ?
C3 C2 C7 . . 117.80(15) ?
C4 C3 C2 . . 121.37(16) ?
C3 C4 C5 . . 120.68(18) ?
C6 C5 C4 . . 120.09(17) ?
C5 C6 C7 . . 121.20(16) ?
C8 C7 C6 . . 121.72(16) ?
C8 C7 C2 . . 119.44(16) ?
C6 C7 C2 . . 118.84(16) ?
C7 C8 C9 . . 121.98(15) ?
C8 C9 C10 . . 121.62(15) ?
C8 C9 C14 . . 119.47(16) ?
C10 C9 C14 . . 118.91(16) ?
C11 C10 C9 . . 121.23(17) ?
C10 C11 C12 . . 120.22(18) ?
C13 C12 C11 . . 120.46(18) ?
C12 C13 C14 . . 121.50(16) ?
C13 C14 C1 . . 122.89(15) ?
C13 C14 C9 . . 117.68(16) ?
C1 C14 C9 . . 119.42(15) ?
C15 C15 C1 3_766 . 179.6(2) ?

