Effective Tuning of the Electronic and Photophysical Properties of Tetrathiafulvalene Pyrroles via Aromatic Heterocycle Annulation
Park, Jung Su; Kim, Jihae; Kim, Yong-Hoon; Sessler, Jonathan L.; RSC Adv.  (2015) –; doi:10.1039/C5RA14811A

data_7221733
_publ_section_title
;
 Effective Tuning of the Electronic and Photophysical Properties of
 Tetrathiafulvalene Pyrroles via Aromatic Heterocycle Annulation
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA14811A
_journal_year                    2015
_chemical_formula_moiety         'C10 H5 N3 S4'
_chemical_formula_sum            'C10 H5 N3 S4'
_chemical_formula_weight         295.41
_chemical_name_common            Pyrazino-tetrathiafulvalene-pyrrole
_chemical_name_systematic
; 
2-(5H-[1,3]dithiolo[4,5-c]pyrrol-2-ylidene)-[1,3]dithiolo[4,5-b]pyrazine 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-06-04 deposited with the CCDC.
2015-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.045(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1660(4)
_cell_length_b                   9.3650(5)
_cell_length_c                   15.1600(9)
_cell_measurement_reflns_used    2763
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     1133.83(11)
_computing_cell_refinement       'Collect Software, Nonius B. V. 1998'
_computing_data_collection       'Collect Software, Nonius B. V. 1998'
_computing_data_reduction
;
SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_sigmaI/netI    0.0990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4691
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  0.98020
_exptl_absorpt_correction_T_min  0.87977
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
XPrep, SHELXTL/PC, Siemens Analytical 
;
_exptl_crystal_colour            Organge
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             600
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.083
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2598
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.0638
_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/[\s^2^(Fo^2^)+(0.0380P)^2^+1.2259P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1257
_reflns_number_gt                1588
_reflns_number_total             2598
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra14811a2.cif
_cod_data_source_block           pzttf
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7221733