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_7151489
_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            'C10 H7 Br N2'
_chemical_formula_weight         235.09
_chemical_melting_point          377.4(3)
_chemical_name_common            2-phenyl-5-bromopyrimidine
_chemical_name_systematic
;
2-phenyl-5-bromopyrimidine
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.27(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.271(1)
_cell_length_b                   21.359(3)
_cell_length_c                   6.932(1)
_cell_measurement_reflns_used    843
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      24.50
_cell_measurement_theta_min      12.00
_cell_volume                     881.7(2)
_computing_cell_refinement       'SMART version 5.060 (Bruker, 1999)'
_computing_data_collection       'SMART version 5.060 (Bruker, 1999)'
_computing_data_reduction        'SAINT version 6.02A (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL version 5.10 (Bruker, 1997)'
_computing_publication_material  'SHELXTL version 5.10 (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0518
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10386
_diffrn_reflns_theta_full        29.06
_diffrn_reflns_theta_max         29.06
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    4.609
_exptl_absorpt_correction_T_max  0.8322
_exptl_absorpt_correction_T_min  0.1486
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
'XPREP (SHELXTL,1997); R(int)=0.102 before correction'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2358
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0287
_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^)+(0.0372P)^2^+0.7319P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0786
_reflns_number_gt                2004
_reflns_number_total             2358
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            b305870k.txt
_cod_data_source_block           (6)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 '104.0--104.5 \%C' was changed to
'377.4(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      P2(1)/c
_cod_database_code               7151489