3,4-Phenylenedioxythiophenes (PheDOTs) functionalized with electron-withdrawing groups and their analogs for organic electronics
Krompiec, Michal P.; Baxter, Sean N.; Klimareva, Elena L.; Yufit, Dmitry S.; Congrave, Daniel G.; Britten, Thomas K.; Perepichka, Igor F.; Journal of Materials Chemistry C 6 (2018) 3743–; doi:10.1039/C7TC05227H

data_7237029
_publ_section_title
;
 3,4-Phenylenedioxythiophenes (PheDOTs) functionalized with
 electron-withdrawing groups and their analogs for organic electronics
;
_journal_issue                   14
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              3743
_journal_paper_doi               10.1039/C7TC05227H
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         'C12 H6 N2 O2 S'
_chemical_formula_sum            'C12 H6 N2 O2 S'
_chemical_formula_weight         242.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-19
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_audit_update_record
;
2017-06-01 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.714(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.43002(16)
_cell_length_b                   21.1250(7)
_cell_length_c                   10.8195(3)
_cell_measurement_reflns_used    3195
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      30.8600
_cell_measurement_theta_min      2.0970
_cell_volume                     1011.40(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -44.00   38.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337   57.0000   30.0000 82

  2 omega  -99.00   14.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  -19.0000 -150.0000 113

  3 omega  -81.00  -11.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  131.0000   34.0000 70

  4 omega  -98.00  -16.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  -77.0000 -180.0000 82

  5 omega  -80.00  -48.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  178.0000   60.0000 32

  6 omega   40.00   88.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -131.0000  -35.0000 48

  7 omega -104.00  -35.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337 -178.0000  150.0000 69

  8 omega  -98.00   -3.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  -77.0000  150.0000 95

  9 omega  -97.00   -7.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  -57.0000   30.0000 90
;
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       \w-scan
_diffrn_orient_matrix_UB_11      -0.0021687000
_diffrn_orient_matrix_UB_12      -0.0335550000
_diffrn_orient_matrix_UB_13      -0.0023406000
_diffrn_orient_matrix_UB_21      -0.1600654000
_diffrn_orient_matrix_UB_22      0.0003986000
_diffrn_orient_matrix_UB_23      0.0010670000
_diffrn_orient_matrix_UB_31      -0.0101249000
_diffrn_orient_matrix_UB_32      0.0012124000
_diffrn_orient_matrix_UB_33      -0.0655304000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14911
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.93
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'sealed tube'
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.4031
_exptl_crystal_size_mid          0.0659
_exptl_crystal_size_min          0.0524
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2675
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0400P)^2^+0.4400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.1033
_reflns_number_gt                2083
_reflns_number_total             2675
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7tc05227h2.cif
_cod_data_source_block           QxDOT_iper3b
_cod_database_code               7237029
_chemical_oxdiff_formula         'C12 H6 N2 O2 S1'
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'