#------------------------------------------------------------------------------
#$Date: 2021-12-07 05:49:59 +0200 (Tue, 07 Dec 2021) $
#$Revision: 271207 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158366.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7158366
loop_
_publ_author_name
'Islam, Khadimul'
'Narjinari, Himani'
'Bisarya, Akshara'
'Kumar, Akshai'
_publ_section_title
;
 Multi-fold Sonogashira coupling: a new and convenient approach to obtain
 tetraalkynyl anthracenes with tunable photophysical properties.
;
_journal_issue                   44
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9692
_journal_page_last               9704
_journal_paper_doi               10.1039/d1ob01861b
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C34 H42 Si4'
_chemical_formula_sum            'C34 H42 Si4'
_chemical_formula_weight         563.04
_chemical_name_common            TTMSEA
_chemical_name_systematic
(anthracene-2,6,9,10-tetrayltetrakis(ethyne-2,1-diyl))tetrakis(trimethylsilane)
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2021-03-17 deposited with the CCDC.	2021-10-19 downloaded from the CCDC.
;
_cell_angle_alpha                99.128(5)
_cell_angle_beta                 96.304(5)
_cell_angle_gamma                105.017(4)
_cell_formula_units_Z            1
_cell_length_a                   6.0741(8)
_cell_length_b                   11.2759(16)
_cell_length_c                   14.146(2)
_cell_measurement_reflns_used    26046
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.91
_cell_volume                     912.3(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26046
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.025
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             302
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0559P)²+0.1866P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1232
_reflns_number_gt                2273
_reflns_number_total             3212
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob01861b2.cif
_cod_data_source_block           adkhantms_0m_a
_cod_depositor_comments
'Adding full bibliography for 7158365--7158370.cif.'
_cod_database_code               7158366
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Si1 Si 0.17824(11) 0.11913(6) 0.71140(5) 0.0646(2) Uani 1 1 d . . .
Si2 Si 1.18241(12) 0.69982(7) 0.87093(5) 0.0762(3) Uani 1 1 d . . .
C2 C 0.0227(3) 0.40612(17) 0.55248(14) 0.0505(5) Uani 1 1 d . . .
C1 C -0.1873(3) 0.39205(17) 0.49253(14) 0.0493(5) Uani 1 1 d . . .
C3 C 0.2095(3) 0.51375(17) 0.56083(13) 0.0493(5) Uani 1 1 d . . .
C5 C 0.6014(4) 0.6366(2) 0.63157(15) 0.0578(5) Uani 1 1 d . . .
C4 C 0.4215(4) 0.53158(19) 0.62202(14) 0.0548(5) Uani 1 1 d . . .
H9 H 0.4383 0.4700 0.6565 0.066 Uiso 1 1 calc R . .
C7 C 0.3811(4) 0.71418(19) 0.51603(15) 0.0586(5) Uani 1 1 d . . .
H12 H 0.3703 0.7754 0.4802 0.070 Uiso 1 1 calc R . .
C8 C 0.0508(4) 0.30997(19) 0.60432(15) 0.0559(5) Uani 1 1 d . . .
C6 C 0.5806(4) 0.7280(2) 0.57517(16) 0.0640(6) Uani 1 1 d . . .
H11 H 0.7051 0.7979 0.5790 0.077 Uiso 1 1 calc R . .
C13 C 0.8062(4) 0.6556(2) 0.70022(16) 0.0647(6) Uani 1 1 d . . .
C9 C 0.0878(4) 0.2318(2) 0.64743(16) 0.0627(6) Uani 1 1 d . . .
C14 C 0.9675(4) 0.6727(2) 0.76302(18) 0.0721(6) Uani 1 1 d . . .
C10 C 0.2607(5) 0.0062(2) 0.6232(2) 0.0935(8) Uani 1 1 d . . .
H2A H 0.1311 -0.0361 0.5733 0.140 Uiso 1 1 calc R . .
H2B H 0.3077 -0.0540 0.6556 0.140 Uiso 1 1 calc R . .
H2C H 0.3862 0.0497 0.5947 0.140 Uiso 1 1 calc R . .
C12 C -0.0620(5) 0.0376(3) 0.7680(2) 0.1018(9) Uani 1 1 d . . .
H1A H -0.1031 0.0975 0.8138 0.153 Uiso 1 1 calc R . .
H1B H -0.0149 -0.0222 0.8009 0.153 Uiso 1 1 calc R . .
H1C H -0.1929 -0.0051 0.7188 0.153 Uiso 1 1 calc R . .
C11 C 0.4269(6) 0.2087(3) 0.8050(3) 0.1305(14) Uani 1 1 d . . .
H3A H 0.5458 0.2556 0.7750 0.196 Uiso 1 1 calc R . .
H3B H 0.4854 0.1520 0.8375 0.196 Uiso 1 1 calc R . .
H3C H 0.3789 0.2651 0.8511 0.196 Uiso 1 1 calc R . .
C15 C 1.4372(5) 0.8278(3) 0.8638(3) 0.1326(13) Uani 1 1 d . . .
H15A H 1.4925 0.8084 0.8039 0.199 Uiso 1 1 calc R . .
H15B H 1.5565 0.8369 0.9171 0.199 Uiso 1 1 calc R . .
H15C H 1.3950 0.9045 0.8667 0.199 Uiso 1 1 calc R . .
C17 C 1.2702(7) 0.5570(3) 0.8780(3) 0.1398(14) Uani 1 1 d . . .
H17A H 1.1356 0.4877 0.8726 0.210 Uiso 1 1 calc R . .
H17B H 1.3669 0.5681 0.9390 0.210 Uiso 1 1 calc R . .
H17C H 1.3541 0.5406 0.8261 0.210 Uiso 1 1 calc R . .
C16 C 1.0440(6) 0.7430(5) 0.9748(2) 0.1580(18) Uani 1 1 d . . .
H16A H 1.0087 0.8206 0.9715 0.237 Uiso 1 1 calc R . .
H16B H 1.1467 0.7524 1.0338 0.237 Uiso 1 1 calc R . .
H16C H 0.9041 0.6786 0.9733 0.237 Uiso 1 1 calc R . .
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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C9 Si1 C10 108.45(12) . . ?
C9 Si1 C11 107.04(13) . . ?
C10 Si1 C11 110.92(15) . . ?
C9 Si1 C12 109.57(12) . . ?
C10 Si1 C12 110.38(14) . . ?
C11 Si1 C12 110.39(17) . . ?
C14 Si2 C16 106.26(13) . . ?
C14 Si2 C17 109.86(15) . . ?
C16 Si2 C17 111.1(2) . . ?
C14 Si2 C15 109.18(14) . . ?
C16 Si2 C15 111.0(2) . . ?
C17 Si2 C15 109.32(18) . . ?
C1 C2 C3 120.36(17) . . ?
C1 C2 C8 120.51(18) . . ?
C3 C2 C8 119.11(18) . . ?
C2 C1 C3 119.76(18) . 2_566 ?
C2 C1 C7 121.86(18) . 2_566 ?
C3 C1 C7 118.38(18) 2_566 2_566 ?
C2 C3 C4 121.62(18) . . ?
C2 C3 C1 119.87(18) . 2_566 ?
C4 C3 C1 118.50(18) . 2_566 ?
C4 C5 C6 119.24(19) . . ?
C4 C5 C13 119.9(2) . . ?
C6 C5 C13 120.8(2) . . ?
C5 C4 C3 121.80(19) . . ?
C5 C4 H9 119.1 . . ?
C3 C4 H9 119.1 . . ?
C6 C7 C1 121.4(2) . 2_566 ?
C6 C7 H12 119.3 . . ?
C1 C7 H12 119.3 2_566 . ?
C9 C8 C2 176.2(2) . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H11 119.7 . . ?
C5 C6 H11 119.7 . . ?
C14 C13 C5 175.0(2) . . ?
C8 C9 Si1 173.6(2) . . ?
C13 C14 Si2 171.5(2) . . ?
Si1 C10 H2A 109.5 . . ?
Si1 C10 H2B 109.5 . . ?
H2A C10 H2B 109.5 . . ?
Si1 C10 H2C 109.5 . . ?
H2A C10 H2C 109.5 . . ?
H2B C10 H2C 109.5 . . ?
Si1 C12 H1A 109.5 . . ?
Si1 C12 H1B 109.5 . . ?
H1A C12 H1B 109.5 . . ?
Si1 C12 H1C 109.5 . . ?
H1A C12 H1C 109.5 . . ?
H1B C12 H1C 109.5 . . ?
Si1 C11 H3A 109.5 . . ?
Si1 C11 H3B 109.5 . . ?
H3A C11 H3B 109.5 . . ?
Si1 C11 H3C 109.5 . . ?
H3A C11 H3C 109.5 . . ?
H3B C11 H3C 109.5 . . ?
Si2 C15 H15A 109.5 . . ?
Si2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
Si2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Si2 C17 H17A 109.5 . . ?
Si2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
Si2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Si2 C16 H16A 109.5 . . ?
Si2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Si2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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
Si1 C9 1.831(2) . ?
Si1 C10 1.842(3) . ?
Si1 C11 1.844(3) . ?
Si1 C12 1.847(3) . ?
Si2 C14 1.826(3) . ?
Si2 C16 1.833(3) . ?
Si2 C17 1.836(3) . ?
Si2 C15 1.847(3) . ?
C2 C1 1.409(3) . ?
C2 C3 1.409(3) . ?
C2 C8 1.436(3) . ?
C1 C3 1.422(3) 2_566 ?
C1 C7 1.424(3) 2_566 ?
C3 C4 1.419(3) . ?
C3 C1 1.422(3) 2_566 ?
C5 C4 1.364(3) . ?
C5 C6 1.422(3) . ?
C5 C13 1.438(3) . ?
C4 H9 0.9300 . ?
C7 C6 1.353(3) . ?
C7 C1 1.424(3) 2_566 ?
C7 H12 0.9300 . ?
C8 C9 1.201(3) . ?
C6 H11 0.9300 . ?
C13 C14 1.201(3) . ?
C10 H2A 0.9600 . ?
C10 H2B 0.9600 . ?
C10 H2C 0.9600 . ?
C12 H1A 0.9600 . ?
C12 H1B 0.9600 . ?
C12 H1C 0.9600 . ?
C11 H3A 0.9600 . ?
C11 H3B 0.9600 . ?
C11 H3C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
