Development of strongly absorbing S,N-heterohexacene-based donor materials for efficient vacuum-processed organic solar cells
Christoph Wetzel; Amaresh Mishra; Elena Mena-Osteritz; Karsten Walzer; Martin Pfeiffer; Peter Bauerle; Journal of Materials Chemistry C 4 (2016) 3715–3725; doi:10.1039/C5TC03539B

data_7234707
_publ_section_title
;
 Development of strongly absorbing S,N-heterohexacene-based donor
 materials for efficient vacuum-processed organic solar cells
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              3715
_journal_page_last               3725
_journal_paper_doi               10.1039/C5TC03539B
_journal_volume                  4
_journal_year                    2016
_chemical_formula_moiety         'C34 H30 N6 S4'
_chemical_formula_sum            'C34 H30 N6 S4'
_chemical_formula_weight         650.88
_chemical_name_systematic        DCV-SN6_Hex
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 96.1585(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.94184(3)
_cell_length_b                   32.8876(2)
_cell_length_c                   19.72071(13)
_cell_measurement_reflns_used    22538
_cell_measurement_temperature    180.00(14)
_cell_measurement_theta_max      76.2490
_cell_measurement_theta_min      4.5010
_cell_volume                     3186.62(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega  -40.00    6.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.0007   38.0000    0.0000 46

  2 omega  -49.00    3.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.0007   38.0000  -30.0000 52

  3 omega -120.00  -94.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.0007  -99.0000  -30.0000 26

  4 omega -124.00  -85.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.0007  -99.0000  -60.0000 39

  5 omega  -74.00   -3.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.0007  125.0000  -60.0000 71

  6 omega -116.00  -12.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.0007  -57.0000 -180.0000 104

  7 omega   72.00   98.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0007 -125.0000   30.0000 26

  8 omega  -28.00    7.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000   30.0000   90.0000 35

  9 omega  -92.00  -34.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000   77.0000 -180.0000 58

 10 omega   48.00   74.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 26

 11 omega   33.00  169.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  150.0000 136

 12 omega  116.00  142.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   60.0000 26

 13 omega   37.00   90.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 53

 14 omega   43.00   91.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 48

 15 omega   55.00   81.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 26

 16 omega   40.00   85.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 45

 17 omega   58.00  116.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  120.0000 58

 18 omega  118.00  166.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000   30.0000 48

 19 omega   59.00  108.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  150.0000 49

 20 omega   80.00  106.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   30.0000 26

 21 omega   92.00  153.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  150.0000 61

 22 omega   78.00  104.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   60.0000 26

 23 omega   36.00   95.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  150.0000 59

 24 omega   60.00   85.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   90.0000 25

 25 omega   61.00   94.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   30.0000 33

 26 omega   89.00  114.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -150.0000 25

 27 omega   40.00   83.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 43

 28 omega   45.00  123.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  120.0000 78

 29 omega   36.00   61.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000    0.0000 25

 30 omega   77.00  116.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000    0.0000 39

 31 omega   59.00  116.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   60.0000 57

 32 omega  114.00  145.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 31

 33 omega   61.00   86.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -30.0000 25

 34 omega   57.00   82.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 25

 35 omega   38.00   98.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -90.0000 60

 36 omega  135.00  173.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000 -180.0000 38

 37 omega   91.00  116.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  -60.0000 25

 38 omega   31.00  149.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  -30.0000 118

 39 omega   57.00  110.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  -90.0000 53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.2350161000
_diffrn_orient_matrix_UB_12      0.0305727000
_diffrn_orient_matrix_UB_13      -0.0023564000
_diffrn_orient_matrix_UB_21      0.0468883000
_diffrn_orient_matrix_UB_22      -0.0154647000
_diffrn_orient_matrix_UB_23      -0.0715533000
_diffrn_orient_matrix_UB_31      -0.2021347000
_diffrn_orient_matrix_UB_32      0.0319475000
_diffrn_orient_matrix_UB_33      -0.0323849000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            34696
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.487
_diffrn_reflns_theta_min         3.508
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.012
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear bluish blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       needle
_exptl_crystal_F_000             1360
_exptl_crystal_preparation       Sublimed
_exptl_crystal_recrystallization_method 'By sublimation'
_exptl_crystal_size_max          0.1718
_exptl_crystal_size_mid          0.1106
_exptl_crystal_size_min          0.0597
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         6665
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+2.0209P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0872
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6430
_reflns_number_total             6665
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            J-Mater-Chem-C-2016-4-3715.cif
_cod_data_source_block           cwe14023
_cod_original_cell_volume        3186.62(4)
_cod_database_code               7234707
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C30-C24 \\sim C30-C35 \\sim C31-C30 \\sim C31-C29 \\sim C35-C34
 with sigma of 0.02
 C35-C34 \\sim C31-C29 \\sim C30-C35 \\sim C31-C30 \\sim C30-C24
 with sigma of 0.02
 C31-C29 \\sim C35-C34 \\sim C30-C35 \\sim C31-C30 \\sim C30-C24
 with sigma of 0.02
3. Rigid bond restraints
 C33, C29, C31, C30, C24
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C30 \\sim C24 \\sim C31 \\sim C29 \\sim C33: within 1.7A with sigma of 0.04 and
sigma for terminal atoms of 0.08
5. Others
 Fixed Sof: C29(0.75) H29A(0.75) H29B(0.75) H30A(0.75) H30B(0.75) H30C(0.25)
 H30D(0.25) C31(0.75) H31A(0.75) H31B(0.75) H33D(0.25) H33E(0.25) H33F(0.25)
 H33A(0.75) H33B(0.75) H33C(0.75) C34(0.25) H34A(0.25) H34B(0.25) C35(0.25)
 H35A(0.25) H35B(0.25) C36(0.25) H36A(0.25) H36B(0.25) C37(0.75) H37A(0.75)
 H37B(0.75)
6.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C21(H21A,H21B), C24(H24A,H24B), C26(H26A,H26B), C27(H27A,
 H27B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C30(H30C,H30D),
 C31(H31A,H31B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B)
6.b Me refined with riding coordinates:
 C33(H33D,H33E,H33F), C33(H33A,H33B,H33C)
6.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C16(H16), C20(H20)
6.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C)
;
_ins_header
;
TITL CWE14023 in P2(1)/c 
REM P2(1)/c (#14 in standard setting)
CELL 1.54184   4.941839  32.887641  19.720706  90.0000  96.1585  90.0000
ZERR    4.00   0.000033   0.000199   0.000132   0.0000   0.0006   0.0000
LATT  1
SYMM -x, y+1/2,-z+1/2 
SFAC C H N S
UNIT 136.00 120.00 24.00 16.00
TREF
HKLF 4
END
;
_olex2_date_sample_completion    2014-05-16
_olex2_date_sample_data_collection 2014-05-14
_olex2_exptl_crystal_mounting_method Manual
_olex2_submission_special_instructions 'No special instructions were received'