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_4001852
_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         'C88 H100 N2 O6,C H2 Cl2,3(C2 H6 O)'
_chemical_formula_sum            'C95 H120 Cl2 N2 O9'
_chemical_formula_weight         1504.82
_chemical_melting_point          477.0(4)
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-06-14
_audit_creation_method
;
  Olex2 1.2-alpha
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                117.735(17)
_cell_angle_beta                 95.132(18)
_cell_angle_gamma                97.491(17)
_cell_formula_units_Z            1
_cell_length_a                   8.8088(13)
_cell_length_b                   16.589(3)
_cell_length_c                   17.178(3)
_cell_measurement_reflns_used    8027
_cell_measurement_temperature    150
_cell_measurement_theta_max      31.8769
_cell_measurement_theta_min      2.8114
_cell_volume                     2170.4(8)
_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-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                 'CCD area detector'
_diffrn_detector_area_resol_mean 0.0350
_diffrn_detector_type            'Rigaku Saturn 724+ CCD area detector'
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device       'CrystalLogic Kappa (3-circle)'
_diffrn_measurement_device_type  'CrystalLogic Kappa 3-circle diffractometer'
_diffrn_measurement_method       'profile data from thick-slice \w-scans'
_diffrn_orient_matrix_UB_11      0.0524285000
_diffrn_orient_matrix_UB_12      0.0071065000
_diffrn_orient_matrix_UB_13      0.0354472000
_diffrn_orient_matrix_UB_21      -0.0306441000
_diffrn_orient_matrix_UB_22      -0.0430849000
_diffrn_orient_matrix_UB_23      -0.0063049000
_diffrn_orient_matrix_UB_31      0.0510687000
_diffrn_orient_matrix_UB_32      -0.0186121000
_diffrn_orient_matrix_UB_33      -0.0279204000
_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  0.0359
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.927
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16158
_diffrn_reflns_point_group_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         24.21
_diffrn_reflns_theta_min         2.40
_diffrn_source
'undulator, beamline I19, Diamond Light Source, RAL'
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0957 before and 0.0499 after correction.
The Ratio of minimum to maximum transmission is 0.7727.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             810
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         7284
_refine_ls_number_restraints     81
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0610
_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^)+(0.1208P)^2^+0.1306P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1805
_refine_ls_wR_factor_ref         0.1943
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5115
_reflns_number_total             7284
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cm4029484_si_002.cif
_cod_data_source_block           OAE7
_cod_original_cell_volume        2170.4(7)
_cod_database_code               4001852
_olex2_refinement_description
;
1. Others
 Fixed Sof: Cl1(0.5) Cl2(0.5) C1(0.5) H1A(0.5) H1B(0.5) O1A(0.75) O1B(0.25)
 N1A(0.5) C2A(0.5) H2A(0.5) C3A(0.5) H3A(0.5) C4A(0.5) C5A(0.5) H5A(0.5)
 C6A(0.5) H6A(0.5) N1B(0.5) C2B(0.5) H2B(0.5) C3B(0.5) H3B(0.5) C4B(0.5)
 C5B(0.5) H5B(0.5) C6B(0.5) H6B(0.5) C28A(0.75) H28A(0.75) H28B(0.75)
 C28B(0.25) H28C(0.25) H28D(0.25) C29A(0.75) H29A(0.75) H29B(0.75) C30A(0.75)
 H30A(0.75) H30B(0.75) C31A(0.75) H31A(0.75) H31B(0.75) C32A(0.75) H32A(0.75)
 H32B(0.75) C33A(0.75) H33A(0.75) H33B(0.75) H33C(0.75) C29B(0.25) H29C(0.25)
 H29D(0.25) C30B(0.25) H30C(0.25) H30D(0.25) C31B(0.25) H31C(0.25) H31D(0.25)
 C32B(0.25) H32C(0.25) H32D(0.25) C33B(0.25) H33D(0.25) H33E(0.25) H33F(0.25)
 C46(0.5) H46A(0.5) H46B(0.5) H46C(0.5) C47(0.5) H47A(0.5) H47B(0.5) O4(0.5)
 H4(0.5)
 Fixed Uiso: H1A(0.081) H1B(0.081) H2A(0.114) H3A(0.087) H5A(0.073) H6A(0.11)
 H2B(0.114) H3B(0.087) H5B(0.073) H6B(0.11) H10(0.061) H11(0.062) H13(0.062)
 H14(0.063) H19(0.06) H22(0.055) H26(0.054) H28A(0.066) H28B(0.066) H28C(0.068)
 H28D(0.068) H29A(0.075) H29B(0.075) H30A(0.074) H30B(0.074) H31A(0.087)
 H31B(0.087) H32A(0.09) H32B(0.09) H33A(0.124) H33B(0.124) H33C(0.124)
 H29C(0.07) H29D(0.07) H30C(0.082) H30D(0.082) H31C(0.057) H31D(0.057)
 H32C(0.126) H32D(0.126) H33D(0.123) H33E(0.123) H33F(0.123) H34A(0.059)
 H34B(0.059) H35A(0.061) H35B(0.061) H36A(0.058) H36B(0.058) H37A(0.058)
 H37B(0.058) H38A(0.067) H38B(0.067) H39A(0.106) H39B(0.106) H39C(0.106)
 H40A(0.056) H40B(0.056) H41A(0.056) H41B(0.056) H42A(0.057) H42B(0.057)
 H43A(0.057) H43B(0.057) H44A(0.068) H44B(0.068) H45A(0.113) H45B(0.113)
 H45C(0.113) H46A(0.121) H46B(0.121) H46C(0.121) H47A(0.107) H47B(0.107)
 Fixed X: H1A(0.7535) H1B(0.7472) H2A(0.5938) H3A(0.5126) H5A(0.7915)
 H6A(0.8838) H2B(0.6647) H3B(0.553) H5B(0.8247) H6B(0.9015) H10(0.2972)
 H11(0.1942) H13(0.5593) H14(0.6598) H19(0.3311) H22(0.008) H26(0.2292)
 H28A(0.5031) H28B(0.5654) H28C(0.4536) H28D(0.5707) H29A(0.7622) H29B(0.7739)
 H30A(0.6379) H30B(0.6615) H31A(0.9156) H31B(0.9384) H32A(0.8076) H32B(0.8177)
 H33A(1.0886) H33B(1.0332) H33C(1.0926) H29C(0.5939) H29D(0.7072) H30C(0.8279)
 H30D(0.7012) H31C(0.9283) H31D(0.7754) H32C(1.0127) H32D(0.8563) H33D(1.111)
 H33E(0.9981) H33F(0.948) H34A(-0.2359) H34B(-0.1547) H35A(-0.3264) H35B(-
 0.4029) H36A(-0.4983) H36B(-0.4177) H37A(-0.6682) H37B(-0.5866) H38A(-0.7559)
 H38B(-0.6784) H39A(-0.9271) H39B(-0.9474) H39C(-0.8521) H40A(0.4145)
 H40B(0.3242) H41A(0.4029) H41B(0.4891) H42A(0.5749) H42B(0.6619) H43A(0.663)
 H43B(0.7448) H44A(0.9122) H44B(0.834) H45A(1.0104) H45B(1.0724) H45C(0.9339)
 H46A(0.8268) H46B(0.7438) H46C(0.6854) H47A(0.597) H47B(0.6571) H4(0.4254)
 Fixed Y: H1A(0.2533) H1B(0.211) H2A(1.4534) H3A(1.2977) H5A(1.3264)
 H6A(1.4783) H2B(1.4692) H3B(1.3114) H5B(1.3144) H6B(1.4702) H10(1.0172)
 H11(0.8601) H13(0.8367) H14(0.9926) H19(0.3819) H22(0.5392) H26(0.102)
 H28A(0.5089) H28B(0.4557) H28C(0.4948) H28D(0.4769) H29A(0.5827) H29B(0.5561)
 H30A(0.7054) H30B(0.6804) H31A(0.7407) H31B(0.7167) H32A(0.8675) H32B(0.8417)
 H33A(0.8916) H33B(0.9631) H33C(0.8743) H29C(0.6445) H29D(0.5727) H30C(0.6142)
 H30D(0.6763) H31C(0.7119) H31D(0.7558) H32C(0.7943) H32D(0.8356) H33D(0.8888)
 H33E(0.9537) H33F(0.8884) H34A(0.4576) H34B(0.4268) H35A(0.2824) H35B(0.3078)
 H36A(0.4282) H36B(0.4063) H37A(0.2815) H37B(0.2583) H38A(0.4052) H38B(0.3786)
 H39A(0.2589) H39B(0.3178) H39C(0.2354) H40A(0.0285) H40B(0.0388) H41A(-0.0938)
 H41B(-0.1071) H42A(0.0516) H42B(0.0369) H43A(-0.0744) H43B(-0.0935)
 H44A(0.0552) H44B(0.0699) H45A(-0.0697) H45B(0.0235) H45C(-0.0535)
 H46A(0.3197) H46B(0.356) H46C(0.3724) H47A(0.2141) H47B(0.197) H4(0.27)
 Fixed Z: H1A(0.1369) H1B(0.0315) H2A(1.0025) H3A(0.9072) H5A(0.7445)
 H6A(0.8537) H2B(0.9929) H3B(0.9) H5B(0.7237) H6B(0.813) H10(0.6953)
 H11(0.6035) H13(0.4722) H14(0.5625) H19(0.2077) H22(0.4055) H26(0.0229)
 H28A(0.1949) H28B(0.2453) H28C(0.1706) H28D(0.2355) H29A(0.3381) H29B(0.2371)
 H30A(0.3502) H30B(0.2507) H31A(0.3965) H31B(0.2972) H32A(0.4131) H32B(0.3117)
 H33A(0.4432) H33B(0.4139) H33C(0.3437) H29C(0.229) H29D(0.1899) H30C(0.3332)
 H30D(0.3775) H31C(0.2813) H31D(0.2892) H32C(0.436) H32D(0.4462) H33D(0.3869)
 H33E(0.4428) H33F(0.3373) H34A(0.3596) H34B(0.4263) H35A(0.3534) H35B(0.2816)
 H36A(0.3944) H36B(0.4678) H37A(0.327) H37B(0.3992) H38A(0.443) H38B(0.5136)
 H39A(0.3713) H39B(0.4732) H39C(0.4448) H40A(-0.0345) H40B(-0.1139) H41A(-
 0.2201) H41B(-0.1419) H42A(-0.1658) H42B(-0.089) H43A(-0.2753) H43B(-0.2001)
 H44A(-0.1366) H44B(-0.2155) H45A(-0.2409) H45B(-0.2443) H45C(-0.3194)
 H46A(0.0795) H46B(0.1655) H46C(0.0841) H47A(-0.0069) H47B(0.0739) H4(0.0566)
;
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.981
_shelxl_version_number           2013-2