# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_Igla_ASZ
_audit_block_doi                 10.5517/ccdc.csd.cc25zr75
_database_code_depnum_ccdc_archive 'CCDC 2025547'
loop_
_audit_author_name
_audit_author_address
'Grzegorz Cichowicz'
;The Czochralski Laboratory of Advanced Crystal Engineering, University of Warsaw
Poland
;
_audit_update_record             
;
2020-08-26 deposited with the CCDC.	2020-10-26 downloaded from the CCDC.
;
_chemical_name_systematic        1,3,5-Triethynylbenzene
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H6'
_chemical_formula_iupac          ?
_chemical_formula_weight         150.17

_chemical_melting_point          ?

_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                   19.0132(10)
_cell_length_b                   3.9430(2)
_cell_length_c                   23.6198(12)
_cell_angle_alpha                90
_cell_angle_beta                 108.101(2)
_cell_angle_gamma                90
_cell_volume                     1683.12(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5460
_cell_measurement_theta_min      3.3045
_cell_measurement_theta_max      25.2597
_cell_measurement_temperature    130.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.657
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.194
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624

_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      130.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            10486
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_theta_min         3.30
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28

_refine_special_details          
;
;

_reflns_number_total             1551
_reflns_number_gt                1258
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0901
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_number_reflns         1551
_refine_ls_number_parameters     110
_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)+(0.0443P)²+0.7794P] 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         0.157
_refine_diff_density_min         -0.123
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0062(12)

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       'APEX3 V2017 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ' '
_computing_publication_material  'APEX3 V2017 (Bruker AXS Inc., 2017)'

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 0.26951(7) 0.5375(3) 0.35353(5) 0.0248(3) Uani d . . . 1 . .
C C2 0.32920(7) 0.4525(3) 0.33401(5) 0.0248(3) Uani d . . . 1 . .
H H2 0.3209 0.3397 0.297 0.03 Uiso calc U . R 1 . .
C C4 0.41308(7) 0.6996(3) 0.42307(5) 0.0266(3) Uani d . . . 1 . .
H H4 0.462 0.7547 0.4468 0.032 Uiso calc U . R 1 . .
C C3 0.40124(7) 0.5328(3) 0.36877(5) 0.0254(3) Uani d . . . 1 . .
C C5 0.35340(7) 0.7858(3) 0.44271(5) 0.0254(3) Uani d . . . 1 . .
C C7 0.19599(7) 0.4463(3) 0.31676(5) 0.0265(3) Uani d . . . 1 . .
C C6 0.28141(7) 0.7044(3) 0.40783(5) 0.0254(3) Uani d . . . 1 . .
H H6 0.2406 0.7626 0.4211 0.03 Uiso calc U . R 1 . .
C C8 0.13745(8) 0.3639(4) 0.28405(6) 0.0317(3) Uani d . . . 1 . .
H H8 0.0906 0.2978 0.2579 0.038 Uiso calc U . R 1 . .
C C9 0.46278(7) 0.4388(3) 0.34863(5) 0.0277(3) Uani d . . . 1 . .
C C10 0.51308(8) 0.3580(4) 0.33193(6) 0.0331(3) Uani d . . . 1 . .
H H10 0.5534 0.2933 0.3186 0.04 Uiso calc U . R 1 . .
C C11 0.36592(7) 0.9557(3) 0.49892(6) 0.0284(3) Uani d . . . 1 . .
C C12 0.37716(8) 1.0974(4) 0.54512(6) 0.0349(4) Uani d . . . 1 . .
H H12 0.3862 1.211 0.5822 0.042 Uiso calc U . R 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 . 1.3920(18) ?
C1 C6 . 1.3960(17) ?
C1 C7 . 1.4432(18) ?
C2 C3 . 1.3970(18) ?
C2 H2 . 0.95 ?
C4 C5 . 1.3947(18) ?
C4 C3 . 1.3958(17) ?
C4 H4 . 0.95 ?
C3 C9 . 1.4417(19) ?
C5 C6 . 1.3981(17) ?
C5 C11 . 1.4395(18) ?
C7 C8 . 1.1862(19) ?
C6 H6 . 0.95 ?
C8 H8 . 0.95 ?
C9 C10 . 1.1858(19) ?
C10 H10 . 0.95 ?
C11 C12 . 1.1847(19) ?
C12 H12 . 0.95 ?

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 C6 . . 120.11(12) ?
C2 C1 C7 . . 118.53(11) ?
C6 C1 C7 . . 121.35(12) ?
C1 C2 C3 . . 120.14(11) ?
C1 C2 H2 . . 119.9 ?
C3 C2 H2 . . 119.9 ?
C5 C4 C3 . . 120.31(12) ?
C5 C4 H4 . . 119.8 ?
C3 C4 H4 . . 119.8 ?
C4 C3 C2 . . 119.71(12) ?
C4 C3 C9 . . 120.56(11) ?
C2 C3 C9 . . 119.72(11) ?
C4 C5 C6 . . 119.79(11) ?
C4 C5 C11 . . 120.11(11) ?
C6 C5 C11 . . 120.09(12) ?
C8 C7 C1 . . 175.97(14) ?
C1 C6 C5 . . 119.94(12) ?
C1 C6 H6 . . 120.0 ?
C5 C6 H6 . . 120.0 ?
C7 C8 H8 . . 180.0 ?
C10 C9 C3 . . 179.28(15) ?
C9 C10 H10 . . 180.0 ?
C12 C11 C5 . . 179.06(15) ?
C11 C12 H12 . . 180.0 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.24(18) ?
C7 C1 C2 C3 . . . . -179.18(11) ?
C5 C4 C3 C2 . . . . 0.08(18) ?
C5 C4 C3 C9 . . . . -179.12(11) ?
C1 C2 C3 C4 . . . . -0.22(18) ?
C1 C2 C3 C9 . . . . 178.98(11) ?
C3 C4 C5 C6 . . . . 0.04(18) ?
C3 C4 C5 C11 . . . . 179.58(11) ?
C2 C1 C6 C5 . . . . -0.12(18) ?
C7 C1 C6 C5 . . . . 179.28(11) ?
C4 C5 C6 C1 . . . . -0.02(18) ?
C11 C5 C6 C1 . . . . -179.56(11) ?


_exptl_crystal_recrystallization_method 'From the Melt'
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
