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_4001851
_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         'C72 H92 N2 O6'
_chemical_formula_sum            'C72 H92 N2 O6'
_chemical_formula_weight         1081.47
_chemical_melting_point          400.9(5)
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-02-07
_audit_creation_method
' Olex2 1.2-alpha (compiled Dec  5 2012 16:20:19, GUI svn.r4385)'
_cell_angle_alpha                90
_cell_angle_beta                 106.733(19)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   24.021(4)
_cell_length_b                   4.8652(9)
_cell_length_c                   28.577(5)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.89
_cell_volume                     3198.3(10)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'CrystalClear-SM Expert2.0 (Rigaku, 2009)'
_computing_data_reduction
;
transformed to Bruker format using Rigaku CrystalClear-SM Expert2.0 
(Rigaku, 2009), then processed 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-2013/2, 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      120
_diffrn_detector_type            'Rigaku Saturn 724+ CCD area detector'
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'CrystalLogic Kappa (3-circle)'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'double crystal Si 111'
_diffrn_radiation_source
'undulator, beamline I19, Diamond Light Source, RAL'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            28193
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         27.399
_diffrn_reflns_theta_min         2.886
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1576 before and 0.0663 after correction.
The Ratio of minimum to maximum transmission is 0.5325.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_description       prism
_exptl_crystal_F_000             1172
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.038(9)
_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   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         7597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0713
_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^)+(0.0566P)^2^+1.7845P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1635
_refine_ls_wR_factor_ref         0.1767
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5892
_reflns_number_total             7597
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cm4029484_si_002.cif
_cod_data_source_block           OAE5
_cod_database_code               4001851
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  {H23A,H23B} of C23, {H28A,H28B} of C28, {H27A,H27B} of C27, H11 of C11, H3
  of C3, {H34A,H34B} of C34, {H21A,H21B} of C21, {H25A,H25B} of C25, {H31A,
  H31B} of C31, {H20A,H20B} of C20, {H33A,H33B} of C33, H15 of C15, H16 of C16,
  {H35A,H35B} of C35, {H32A,H32B} of C32, {H22A,H22B} of C22, {H19A,H19B} of
  C19, {H26A,H26B} of C26, H8 of C8, {H29A,H29B} of C29, H17 of C17, H18 of C18
 At 1.5 times of:
  {H24A,H24B,H24C} of C24, {H30A,H30B,H30C} of C30, {H36A,H36B,H36C} of C36
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,
 H23B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B),
 C29(H29A,H29B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B),
  C35(H35A,H35B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C11(H11), C15(H15), C16(H16), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C30(H30A,H30B,H30C), C36(H36A,H36B,H36C)
;
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.990
_shelxl_version_number           2012-9