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_7237028
_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         'C9 H3 Cl2 N O2 S'
_chemical_formula_sum            'C9 H3 Cl2 N O2 S'
_chemical_formula_weight         260.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-20
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;
_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                 110.094(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.0302(5)
_cell_length_b                   5.89058(13)
_cell_length_c                   18.9311(6)
_cell_measurement_reflns_used    5586
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      32.5030
_cell_measurement_theta_min      2.2630
_cell_volume                     1888.25(10)
_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  -68.00  -34.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  106.0000 -132.0000 34

  2 omega   45.00   84.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -178.0000  -60.0000 39

  3 omega   16.00   71.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000   30.0000 55

  4 omega   46.00   71.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000  150.0000 25

  5 omega  -29.00   45.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  -57.0000  -90.0000 74

  6 omega   13.00   95.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000  150.0000 82

  7 omega  -44.00   73.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  -19.0000  -30.0000 117

  8 omega  -97.00   -7.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  -57.0000  -90.0000 90

  9 omega -104.00  -35.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337 -178.0000   30.0000 69

 10 omega  -98.00  -73.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  -77.0000 -180.0000 25

 11 omega  -98.00    2.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  -77.0000   30.0000 100
;
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0237448000
_diffrn_orient_matrix_UB_12      -0.0058001000
_diffrn_orient_matrix_UB_13      -0.0385762000
_diffrn_orient_matrix_UB_21      -0.0122032000
_diffrn_orient_matrix_UB_22      0.1138820000
_diffrn_orient_matrix_UB_23      0.0014484000
_diffrn_orient_matrix_UB_31      0.0322738000
_diffrn_orient_matrix_UB_32      0.0387806000
_diffrn_orient_matrix_UB_33      -0.0100487000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14968
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.29
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'sealed tube'
_exptl_absorpt_coefficient_mu    0.880
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_type   analytical
_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)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.830
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.2578
_exptl_crystal_size_mid          0.2007
_exptl_crystal_size_min          0.0329
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2764
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0309
_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^)+(0.0330P)^2^+0.9500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0743
_reflns_number_gt                2383
_reflns_number_total             2764
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7tc05227h2.cif
_cod_data_source_block           56Cl2_PyDOT_iper6
_cod_original_cell_volume        1888.26(9)
_cod_database_code               7237028
_chemical_oxdiff_formula         'C9 H3 N1 O2 Cl2 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'