Oligo(aryleneethynylene)s with Terminal Pyridyl Groups: Synthesis and Length Dependence of the Tunneling-to-Hopping Transition of Single-Molecule Conductances
Zhao, Xiaotao; Huang, Cancan; Gulcur, Murat; Batsanov, Andrei S.; Baghernejad, Masoud; Hong, Wenjing; Bryce, Martin R.; Wandlowski, Thomas; Chemistry of Materials 25 (2013) 4340–; doi:10.1021/cm4029484

data_4001850
_publ_section_title
;
 Oligo(aryleneethynylene)s with Terminal Pyridyl Groups: Synthesis and
 Length Dependence of the Tunneling-to-Hopping Transition of
 Single-Molecule Conductances
;
_journal_issue                   21
_journal_name_full               'Chemistry of Materials'
_journal_page_first              4340
_journal_paper_doi               10.1021/cm4029484
_journal_volume                  25
_journal_year                    2013
_chemical_formula_moiety         'C52 H64 N2 O4'
_chemical_formula_sum            'C52 H64 N2 O4'
_chemical_formula_weight         781.05
_chemical_melting_point          380.4(3)
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   Fourier
_audit_creation_date             2012-10-24
_audit_creation_method
' Olex2 1.2-alpha (compiled Oct  4 2012 14:26:41, GUI svn.r4365)'
_cell_angle_alpha                90
_cell_angle_beta                 94.17(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2332(19)
_cell_length_b                   9.4949(15)
_cell_length_c                   38.973(6)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.30
_cell_volume                     4514.8(12)
_computing_cell_refinement       'Rigaku CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'Rigaku CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction
;
Rigaku CrystalClear (Rigaku Inc., 2008), then transformed to Bruker format 
using APEX2 
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL-2012, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122
;
_computing_structure_solution
'XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122'
_diffrn_ambient_temperature      150
_diffrn_detector_type            'Rigaku Saturn 724+ CCD area detector'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
  1 omega  -60.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000    0.0000    0.0000 175

  2 omega  -60.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -50.0000    0.0000 120

  3 omega  -60.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -50.0000  120.0000 120

  4 omega  -60.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -50.0000  240.0000 120
;
_diffrn_measurement_device
'Crystal Logic 4-circle \k-goniometer (Rigaku Inc.)'
_diffrn_measurement_method       'thick-slice \w scans'
_diffrn_radiation_monochromator  'double crystal Si 111'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            34609
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        24.208
_diffrn_reflns_theta_max         24.208
_diffrn_reflns_theta_min         1.660
_diffrn_source
'undulator, Beamline I19, Diamond Light Source, RAL'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1010 before and 0.0606 after correction.
The Ratio of minimum to maximum transmission is 0.7687.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_description       plate
_exptl_crystal_F_000             1688
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0160(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         7815
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0515
_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^)+(0.0612P)^2^+1.0467P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1352
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5607
_reflns_number_total             7815
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cm4029484_si_002.cif
_cod_data_source_block           OAE4
_cod_database_code               4001850
_diffrn_reflns_sigmai/neti       0.0482
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H2 of C2, H3 of C3, H25 of C25, {H421,H422} of C42, H5 of C5, H6 of C6, H11
  of C11, H14 of C14, H18 of C18, H21 of C21, H24 of C24, {H321,H322} of C32,
  {H311,H312} of C31, {H331,H332} of C33, {H291,H292} of C29, {H491,H492} of
  C49, {H453,H454} of C45B, {H391,H392} of C39, {H371,H372} of C37, {H431,H432}
  of C43, H27 of C27, {H471,H472} of C47, {H301,H302} of C30, {H351,H352} of
  C35, {H451,H452} of C45A, {H443,H444} of C44B, {H481,H482} of C48, {H411,
  H412} of C41, {H501,H502} of C50, {H441,H442} of C44A, {H511,H512} of C51,
  {H381,H382} of C38, H28 of C28, {H361,H362} of C36
 At 1.5 times of:
  {H461,H462,H463} of C46A, {H464,H465,H466} of C46B
2. Restrained distances
 C46A-C45A ~ C45B-C46B
 with sigma of 0.02
 C45A-C44B ~ C44B-C45B
 with sigma of 0.02
 C45A-C44B ~ C44B-C45B
 with sigma of 0.02
 C45A-C44A ~ C44B-C45B
 with sigma of 0.02
3. Others
 Uiso(H521)=Uiso(H522)=Uiso(H523)
 Uiso(H341)=Uiso(H342)=Uiso(H343)
 Uiso(H401)=Uiso(H402)=Uiso(H403)
 Fixed Sof: C44A(0.7) H441(0.7) H442(0.7) C45A(0.7) H451(0.7) H452(0.7)
 C46A(0.7) H461(0.7) H462(0.7) H463(0.7) C44B(0.3) H443(0.3) H444(0.3)
 C45B(0.3) H453(0.3) H454(0.3) C46B(0.3) H464(0.3) H465(0.3) H466(0.3)
4.a Riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C11(H11), C14(H14), C18(H18), C21(H21),
 C24(H24), C25(H25), C27(H27), C28(H28), C29(H291,H292), C30(H301,H302),
 C31(H311,H312), C32(H321,H322), C33(H331,H332), C35(H351,H352), C36(H361,H362),
  C37(H371,H372), C38(H381,H382), C39(H391,H392), C41(H411,H412), C42(H421,
 H422), C43(H431,H432), C44A(H441,H442), C45A(H451,H452), C46A(H461,H462,H463),
 C44B(H443,H444), C45B(H453,H454), C46B(H464,H465,H466), C47(H471,H472),
 C48(H481,H482), C49(H491,H492), C50(H501,H502), C51(H511,H512)
4.b Rotating group:
 C34(H341,H342,H343), C40(H401,H402,H403), C52(H521,H522,H523)
;
_shelx_estimated_absorpt_t_max   1.000
_shelx_estimated_absorpt_t_min   0.991
_shelxl_version_number           2012-4