Multi-fold Sonogashira coupling: a new and convenient approach to obtain tetraalkynyl anthracenes with tunable photophysical properties.
Islam, Khadimul; Narjinari, Himani; Bisarya, Akshara; Kumar, Akshai; Organic & biomolecular chemistry 19 (2021) 9692–9704; doi:10.1039/d1ob01861b

data_7158370
_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 &amp; 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         'C50 H34'
_chemical_formula_sum            'C50 H34'
_chemical_formula_weight         634.77
_chemical_name_common            TTEA
_chemical_name_systematic        2,6,9,10-tetrakis(p-tolylethynyl)anthracene
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 c 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                90.00
_cell_angle_beta                 92.393(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.929(3)
_cell_length_b                   11.922(3)
_cell_length_c                   10.529(2)
_cell_measurement_reflns_used    45579
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.58
_cell_volume                     1872.4(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.1745
_diffrn_reflns_av_sigmaI/netI    0.1288
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            45579
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             668
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane + Methanol'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         6588
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1812
_refine_ls_R_factor_gt           0.0836
_refine_ls_shift/su_max          0.326
_refine_ls_shift/su_mean         0.073
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1015P)^2^+0.5480P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1984
_refine_ls_wR_factor_ref         0.2604
_reflns_number_gt                3080
_reflns_number_total             6588
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob01861b2.cif
_cod_data_source_block           anphch3_b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7158365--7158370.cif.
;
_cod_original_cell_volume        1872.3(7)
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               7158370