Carbon-rich molecules: synthesis and isolation of aryl/heteroaryl terminal bis(butadiynes) (HCC–CC–Ar–CC–CCH) and their applications in the synthesis of oligo(arylenebutadiynylene) molecular wires
West, Kara; Wang, Changsheng; Batsanov, Andrei S.; Bryce, Martin R.; Organic & Biomolecular Chemistry 6 (2008) 1934–1937; doi:10.1039/b802968g

data_7150911
_publ_section_title
;
 Carbon-rich molecules: synthesis and isolation of aryl/heteroaryl
 terminal bis(butadiynes)
 (HC&#xE002;C--C&#xE002;C--Ar--C&#xE002;C--C&#xE002;CH) and their
 applications in the synthesis of oligo(arylenebutadiynylene) molecular
 wires
;
_journal_issue                   11
_journal_name_full               'Organic &amp;  Biomolecular Chemistry'
_journal_page_first              1934
_journal_page_last               1937
_journal_paper_doi               10.1039/b802968g
_journal_volume                  6
_journal_year                    2008
_chemical_formula_moiety         'C13 H5 N'
_chemical_formula_sum            'C13 H5 N'
_chemical_formula_weight         175.18
_chemical_name_common            2,5-bis(buta-1,3-diynyl)-pyridine
_chemical_name_systematic        ' 2,5-bis(buta-1,3-diynyl)-pyridine'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.91(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.7926(8)
_cell_length_b                   20.217(4)
_cell_length_c                   12.385(3)
_cell_measurement_reflns_used    408
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      22.7
_cell_measurement_theta_min      2.6
_cell_volume                     946.1(4)
_computing_cell_refinement       'SAINT version 6.02A (Bruker, 2001)'
_computing_data_collection       'SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT version 6.02A (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL version 6.14 (Bruker, 2003)'
_computing_publication_material  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_refinement  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_solution    'SHELXTL version 6.14 (Bruker, 2003)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART 6K CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1512
_diffrn_reflns_av_sigmaI/netI    0.1255
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8467
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.14
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.865
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.865
_refine_ls_R_factor_all          0.1796
_refine_ls_R_factor_gt           0.0686
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1072P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1609
_refine_ls_wR_factor_ref         0.2080
_reflns_number_gt                683
_reflns_number_total             1685
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            b802968g.txt
_cod_data_source_block           4d
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        946.2(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7150911
_exptl_twin_twinlaw_details      '1 0 0 0 -1 0 -0.5 0 -1'