New pyrimidine- and fluorene-containing oligo(arylene)s: synthesis, crystal structures, optoelectronic properties and a theoretical study Electronic supplementary information (ESI) available: experimental synthetic procedures for compounds 4, 9 and 10; HF/6?31G(d,p) and B3LYP/6?31G(d,p) calculated geometries and frontier orbitals for compounds 13E, 14E and 16E?21E. See http://www.rsc.org/suppdata/ob/b3/b305870k/
Hughes, Gregory; Wang, Changsheng; Batsanov, Andrei S.; Fern, Michael; Frank, Stephen; Bryce, Martin R.; Perepichka, Igor F.; Monkman, Andrew P.; Lyons, Benjamin P.; Organic & Biomolecular Chemistry 1 (2003) 3069–; doi:10.1039/b305870k

data_7151491
_publ_section_title
;
 New pyrimidine- and fluorene-containing oligo(arylene)s: synthesis,
 crystal structures, optoelectronic properties and a theoretical study
 Electronic supplementary information (ESI) available: experimental
 synthetic procedures for compounds 4, 9 and 10; HF/6?31G(d,p) and
 B3LYP/6?31G(d,p) calculated geometries and frontier orbitals for
 compounds 13E, 14E and 16E?21E. See
 http://www.rsc.org/suppdata/ob/b3/b305870k/
;
_journal_issue                   17
_journal_name_full               'Organic &amp;  Biomolecular Chemistry'
_journal_page_first              3069
_journal_paper_doi               10.1039/b305870k
_journal_volume                  1
_journal_year                    2003
_chemical_formula_sum            'C33 H36 Br2 N4'
_chemical_formula_weight         648.48
_chemical_melting_point          452.7(3)
_chemical_name_common
2,7-bis(5-bromo-2-pyrimidyl)-9,9-dihexylfluorene
_chemical_name_systematic
' 2,7-bis(5-bromo-2-pyrimidyl)-9,9-dihexylfluorene'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.37(1)
_cell_angle_beta                 93.99(1)
_cell_angle_gamma                95.14(1)
_cell_formula_units_Z            2
_cell_length_a                   10.244(3)
_cell_length_b                   10.979(3)
_cell_length_c                   13.520(3)
_cell_measurement_reflns_used    654
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.5
_cell_measurement_theta_min      12.0
_cell_volume                     1507.6(7)
_computing_cell_refinement       'SMART-NT V5.0 (Bruker, 1998)'
_computing_data_collection       'SMART-NT V5.0 (Bruker, 1998)'
_computing_data_reduction        'SMART-NT V5.0 (Bruker, 1998)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'SMART 1K 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  0.1187
_diffrn_reflns_av_sigmaI/netI    0.1006
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16402
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.5
_exptl_absorpt_coefficient_mu    2.717
_exptl_absorpt_correction_T_max  0.7780
_exptl_absorpt_correction_T_min  0.4361
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
'XPREP (SHELXTL), R(int)=0.158 before correction'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.1
_refine_diff_density_max         4.345
_refine_diff_density_min         -1.010
_refine_diff_density_rms         0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         6944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.1197
_refine_ls_R_factor_gt           0.0941
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1314P)^2^+10.9455P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2573
_refine_ls_wR_factor_ref         0.2780
_reflns_number_gt                5144
_reflns_number_total             6944
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            b305870k.txt
_cod_data_source_block           (15)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/adriana/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 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '179.3--179.8 \%C' was changed to
'452.7(3)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151491