A novel angularly fused bistetracene: facile synthesis, crystal packing and single-crystal field effect transistors
Zunzhi Wang; Rongjin Li; Yulan Chen; Yuan-Zhi Tan; Zeyi Tu; Xuejiao J. Gao; Huanli Dong; Yuanping Yi; Yu Zhang; Wenping Hu; Klaus Mullen; Long Chen; Journal of Materials Chemistry C 5 (2017) 1308–1312; doi:10.1039/C6TC04365H

data_7235171
_publ_section_title
;
 A novel angularly fused bistetracene: facile synthesis, crystal packing
 and single-crystal field effect transistors
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              1308
_journal_page_last               1312
_journal_paper_doi               10.1039/C6TC04365H
_journal_volume                  5
_journal_year                    2017
_chemical_formula_moiety         '2(C63 H76 Si3)'
_chemical_formula_sum            'C126 H152 Si6'
_chemical_formula_weight         1835.01
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   33.707(2)
_cell_length_b                   16.5828(12)
_cell_length_c                   19.1233(11)
_cell_measurement_reflns_used    1243
_cell_measurement_temperature    105.5(10)
_cell_measurement_theta_max      46.5440
_cell_measurement_theta_min      4.3910
_cell_volume                     10689.1(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      105.5(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3415
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.926
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
  1 omega -119.00  -93.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7424  -99.0000   30.0000 26

  2 omega -124.00  -99.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7424  -99.0000  -60.0000 25

  3 omega -124.00  -92.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7424  -99.0000 -150.0000 32

  4 omega -118.00  -80.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.7424  -99.0000  120.0000 38

  5 omega   85.00  121.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       41.7424  178.0000  120.0000 36

  6 omega   14.00   65.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       90.7981  -30.0000  150.0000 51

  7 omega  102.00  163.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       90.7981  125.0000 -120.0000 61

  8 omega  109.00  159.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       90.7981  125.0000 -180.0000 50

  9 omega    9.00   85.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       90.7981  -15.0000 -150.0000 76
;
_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      0.0335810000
_diffrn_orient_matrix_UB_12      -0.0609677000
_diffrn_orient_matrix_UB_13      -0.0134785000
_diffrn_orient_matrix_UB_21      0.0299814000
_diffrn_orient_matrix_UB_22      0.0580686000
_diffrn_orient_matrix_UB_23      0.0341976000
_diffrn_orient_matrix_UB_31      -0.0079716000
_diffrn_orient_matrix_UB_32      -0.0391184000
_diffrn_orient_matrix_UB_33      0.0717160000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1867
_diffrn_reflns_av_unetI/netI     0.2700
_diffrn_reflns_Laue_measured_fraction_full 0.926
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            24659
_diffrn_reflns_point_group_measured_fraction_full 0.649
_diffrn_reflns_point_group_measured_fraction_max 0.681
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         65.531
_diffrn_reflns_theta_min         3.764
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic green'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_F_000             3968
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1143
_refine_ls_number_reflns         12544
_refine_ls_number_restraints     694
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.2881
_refine_ls_R_factor_gt           0.1100
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0453P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2010
_refine_ls_wR_factor_ref         0.2958
_reflns_Friedel_coverage         0.357
_reflns_Friedel_fraction_full    0.353
_reflns_Friedel_fraction_max     0.371
_reflns_number_gt                3897
_reflns_number_total             12544
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            J-Mater-Chem-C-2017-5-1308.cif
_cod_data_source_block           exp_5990
_cod_original_cell_volume        10689.1(13)
_cod_database_code               7235171
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.871
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C8AA-C17
 1.55 with sigma of 0.02
 C0BA-C75
 1.55 with sigma of 0.02
 C8AA-C0AA
 1.55 with sigma of 0.02
 C0BA-C80
 1.55 with sigma of 0.02
 C1C-C2BA
 1.55 with sigma of 0.01
 C91-C1O
 1.55 with sigma of 0.02
 C1I-C1O
 1.55 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C1G \\sim C95 \\sim C5BA: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.08
C1E \\sim C85 \\sim C20: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
Uanis(C17) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.02
Uanis(C0AA) \\sim Ueq, Uanis(C8AA) \\sim Ueq, Uanis(C4CA) \\sim Ueq,
Uanis(C9BA) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C0CA) \\sim Ueq, Uanis(C5)
\\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C5AA) \\sim Ueq,
Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C12)
\\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq,
Uanis(C9AA) \\sim Ueq, Uanis(C4AA) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19)
\\sim Ueq, Uanis(C7AA) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C22) \\sim Ueq,
Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C26)
\\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C29) \\sim Ueq,
Uanis(C30) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C3CA)
\\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C36) \\sim Ueq,
Uanis(C37) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C39) \\sim Ueq, Uanis(C40)
\\sim Ueq, Uanis(C5CA) \\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C43) \\sim Ueq,
Uanis(C44) \\sim Ueq, Uanis(C45) \\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C47)
\\sim Ueq, Uanis(C48) \\sim Ueq, Uanis(C49) \\sim Ueq, Uanis(C50) \\sim Ueq,
Uanis(C51) \\sim Ueq, Uanis(C52) \\sim Ueq, Uanis(C53) \\sim Ueq, Uanis(C54)
\\sim Ueq, Uanis(C55) \\sim Ueq, Uanis(C57) \\sim Ueq, Uanis(C58) \\sim Ueq,
Uanis(C59) \\sim Ueq, Uanis(C60) \\sim Ueq, Uanis(C61) \\sim Ueq, Uanis(C62)
\\sim Ueq, Uanis(C63) \\sim Ueq, Uanis(C64) \\sim Ueq, Uanis(C65) \\sim Ueq,
Uanis(C66) \\sim Ueq, Uanis(C67) \\sim Ueq, Uanis(C68) \\sim Ueq, Uanis(C69)
\\sim Ueq, Uanis(C70) \\sim Ueq, Uanis(C71) \\sim Ueq, Uanis(C72) \\sim Ueq,
Uanis(C73) \\sim Ueq, Uanis(C75) \\sim Ueq, Uanis(C76) \\sim Ueq, Uanis(C77)
\\sim Ueq, Uanis(C78) \\sim Ueq, Uanis(C79) \\sim Ueq, Uanis(C80) \\sim Ueq,
Uanis(C81) \\sim Ueq, Uanis(C82) \\sim Ueq, Uanis(C83) \\sim Ueq, Uanis(C84)
\\sim Ueq, Uanis(C86) \\sim Ueq, Uanis(C87) \\sim Ueq, Uanis(C88) \\sim Ueq,
Uanis(C89) \\sim Ueq, Uanis(C92) \\sim Ueq, Uanis(C93) \\sim Ueq, Uanis(C94)
\\sim Ueq, Uanis(C95) \\sim Ueq, Uanis(C1D) \\sim Ueq, Uanis(C1G) \\sim Ueq,
Uanis(C1J) \\sim Ueq, Uanis(C1L) \\sim Ueq, Uanis(C1M) \\sim Ueq, Uanis(C1N)
\\sim Ueq, Uanis(C1P) \\sim Ueq, Uanis(C1Q) \\sim Ueq, Uanis(C0AA) \\sim Ueq,
Uanis(C2AA) \\sim Ueq, Uanis(C3AA) \\sim Ueq, Uanis(C8AA) \\sim Ueq, Uanis(C17)
\\sim Ueq, Uanis(C6AA) \\sim Ueq, Uanis(C0BA) \\sim Ueq, Uanis(C1AA) \\sim Ueq,
Uanis(C3BA) \\sim Ueq, Uanis(C1BA) \\sim Ueq, Uanis(C4BA) \\sim Ueq,
Uanis(C5BA) \\sim Ueq, Uanis(C8BA) \\sim Ueq, Uanis(C7BA) \\sim Ueq, : with
sigma of 0.005 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: H83(0.5) H83A(0.5) C91(0.5) H91A(0.5) H91B(0.5) H91C(0.5) C1B(0.5)
 H1B(0.5) C1I(0.5) H1IA(0.5) H1IB(0.5) H1IC(0.5) H1O(0.5) H1OA(0.5) C8BA(0.5)
 H8BA(0.5) H8BB(0.5) H8BC(0.5) C7BA(0.5) H7BA(0.5) H7BB(0.5) H7BC(0.5) C4(0.5)
 H4A(0.5) H4B(0.5) H4C(0.5) C1CA(0.5) H1CA(0.5) H1CB(0.5) H1CC(0.5) C2CA(0.5)
 H2CA(0.5) H2CB(0.5) H2CC(0.5) C2(0.5) H2A(0.5) H2B(0.5) H2C(0.5) C33(0.5)
 H33(0.5) C6CA(0.5) H6CA(0.5) H6CB(0.5) H6CC(0.5) C16(0.5) H16A(0.5) H16B(0.5)
 H16C(0.5)
5.a Ternary CH refined with riding coordinates:
 C58(H58), C62(H62), C72(H72), C76(H76), C78(H78), C79(H79), C83(H83),
 C83(H83A), C88(H88), C1B(H1B), C1C(H1CD), C1E(H1E), C1G(H1G), C1L(H1L),
 C1O(H1O), C1O(H1OA), C1Q(H1Q), C8AA(H8AA), C0BA(H0BA), C33(H33), C41(H41)
5.b Me refined with riding coordinates:
 C66(H66A,H66B,H66C), C69(H69A,H69B,H69C), C75(H75A,H75B,H75C), C77(H77A,H77B,
 H77C), C80(H80A,H80B,H80C), C81(H81A,H81B,H81C), C85(H85A,H85B,H85C), C86(H86A,
 H86B,H86C), C91(H91A,H91B,H91C), C92(H92A,H92B,H92C), C93(H93A,H93B,H93C),
 C94(H94A,H94B,H94C), C95(H95A,H95B,H95C), C1A(H1AA,H1AB,H1AC), C1D(H1DA,H1DB,
 H1DC), C1I(H1IA,H1IB,H1IC), C1J(H1JA,H1JB,H1JC), C1M(H1MA,H1MB,H1MC), C1N(H1NA,
 H1NB,H1NC), C0AA(H0AA,H0AB,H0AC), C2AA(H2AA,H2AB,H2AC), C3AA(H3AA,H3AB,H3AC),
 C17(H17A,H17B,H17C), C6AA(H6AA,H6AB,H6AC), C20(H20A,H20B,H20C), C1AA(H1AD,H1AE,
 H1AF), C3BA(H3BA,H3BB,H3BC), C1BA(H1BA,H1BB,H1BC), C4BA(H4BA,H4BB,H4BC),
 C2BA(H2BA,H2BB,H2BC), C5BA(H5BA,H5BB,H5BC), C8BA(H8BA,H8BB,H8BC), C7BA(H7BA,
 H7BB,H7BC), C4(H4A,H4B,H4C), C1CA(H1CA,H1CB,H1CC), C2CA(H2CA,H2CB,H2CC),
 C2(H2A,H2B,H2C), C1(H1A,H1C,H1D), C8(H8A,H8B,H8C), C6CA(H6CA,H6CB,H6CC),
 C16(H16A,H16B,H16C)
5.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C24(H24), C27(H27), C28(H28), C5CA(H5CA), C43(H43), C44(H44),
 C46(H46), C47(H47), C48(H48), C50(H50), C51(H51), C52(H52), C57(H57), C59(H59),
  C63(H63), C64(H64), C67(H67), C68(H68), C71(H71), C73(H73), C82(H82),
 C84(H84), C87(H87), C89(H89), C1P(H1P)
;