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_4001853
_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         'C84 H80 N2 O4,C4 H8 O2'
_chemical_formula_sum            'C88 H88 N2 O6'
_chemical_formula_weight         1269.60
_chemical_melting_point          473.2(6)
_chemical_name_systematic
;
 ?
;
_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   geom
_audit_creation_date             2013-06-17
_audit_creation_method
;
  Olex2 1.2-alpha
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.222(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   19.637(7)
_cell_length_b                   8.175(3)
_cell_length_c                   23.803(8)
_cell_measurement_reflns_used    8321
_cell_measurement_temperature    150
_cell_measurement_theta_max      24.026
_cell_measurement_theta_min      2.660
_cell_volume                     3537(2)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'CrystalClear-SM Expert2.0 (Rigaku, 2009)'
_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
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 0.0350
_diffrn_detector_type            'Rigaku Saturn 724+ CCD area detector'
_diffrn_measured_fraction_theta_full 0.929
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       'CrystalLogic Kappa (3-circle)'
_diffrn_measurement_method       'profile data from thick-slice \w-scans'
_diffrn_radiation_collimation    '0.3 x 1.5 Double Pinhole'
_diffrn_radiation_monochromator  'double crystal Si 111'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.929
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25970
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         24.053
_diffrn_reflns_theta_min         2.232
_diffrn_source
'undulator, beamline I19, Diamond Light Source, RAL'
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1084 before and 0.0492 after correction.
The Ratio of minimum to maximum transmission is 0.8484.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_description       plate
_exptl_crystal_F_000             1356
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.066(6)
_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   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         5950
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0716P)^2^+0.9445P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1449
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4344
_reflns_number_total             5950
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cm4029484_si_002.cif
_cod_data_source_block           OAE8
_cod_database_code               4001853
_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
 C40-C39B \\sim C39B-C38B \\sim C38B-C37
 with sigma of 0.02
3. Others
 Fixed Sof: C38A(0.92) H38A(0.92) H38B(0.92) C39A(0.92) H39A(0.92) H39B(0.92)
 C38B(0.08) H38C(0.08) H38D(0.08) C39B(0.08) H39C(0.08) H39D(0.08) O1S(0.35)
 O2S(0.35) C1S(0.33) C2S(0.33) C3S(0.15) C4S(0.15) C5S(0.25) C6S(0.5) C7S(0.29)
4.a Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,
 H35B), C37(H37A,H37B), C38A(H38A,H38B), C39A(H39A,H39B), C38B(H38C,H38D),
 C39B(H39C,H39D), C40(H40A,H40B), C41(H41A,H41B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14),
 C18(H18), C19(H19), C21(H21), C22(H22), C27(H27), C30(H30)
4.c Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C42(H42A,H42B,H42C)
;
_shelxl_version_number           2013-2