#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/14/7151491.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7151491
loop_
_publ_author_name
'Hughes, Gregory'
'Wang, Changsheng'
'Batsanov, Andrei S.'
'Fern, Michael'
'Frank, Stephen'
'Bryce, Martin R.'
'Perepichka, Igor F.'
'Monkman, Andrew P.'
'Lyons, Benjamin P.'
_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 &  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       'ω 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/[σ²(Fo²)+(0.1314P)²+10.9455P] where P=(Fo²+2Fc²)/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>2σ(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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.68059(9) 0.53389(7) 1.87517(5) 0.0339(3) Uani 1 1 d . . .
Br2 Br 0.74665(8) 0.99483(7) 0.56660(5) 0.0312(2) Uani 1 1 d . . .
N1 N 0.7351(6) 0.6322(6) 1.5907(5) 0.0291(14) Uani 1 1 d . . .
N2 N 0.5063(6) 0.6262(6) 1.6115(5) 0.0249(12) Uani 1 1 d . . .
N3 N 0.7666(6) 0.9092(6) 0.8580(5) 0.0265(13) Uani 1 1 d . . .
N4 N 0.5407(6) 0.8896(6) 0.8024(4) 0.0242(12) Uani 1 1 d . . .
C1 C 0.5385(6) 0.7531(6) 1.2629(5) 0.0173(12) Uani 1 1 d . . .
C2 C 0.6691(6) 0.7472(6) 1.3023(5) 0.0173(12) Uani 1 1 d . . .
C3 C 0.6938(6) 0.7114(6) 1.3972(5) 0.0204(13) Uani 1 1 d . . .
H3 H 0.7814 0.7067 1.4233 0.024 Uiso 1 1 d R . .
C4 C 0.5879(7) 0.6819(6) 1.4555(5) 0.0188(13) Uani 1 1 d . . .
C5 C 0.4583(6) 0.6898(6) 1.4154(5) 0.0195(13) Uani 1 1 d . . .
H5 H 0.3872 0.6705 1.4548 0.023 Uiso 1 1 d R . .
C6 C 0.4326(6) 0.7253(6) 1.3199(5) 0.0190(13) Uani 1 1 d . . .
H6 H 0.3451 0.7306 1.2939 0.023 Uiso 1 1 d R . .
C7 C 0.5434(6) 0.7888(6) 1.1603(4) 0.0147(12) Uani 1 1 d . . .
C8 C 0.6755(6) 0.8087(6) 1.1381(5) 0.0170(12) Uani 1 1 d . . .
C9 C 0.7069(6) 0.8410(6) 1.0464(5) 0.0162(12) Uani 1 1 d . . .
H9 H 0.7962 0.8551 1.0324 0.019 Uiso 1 1 d R . .
C10 C 0.6060(6) 0.8532(6) 0.9724(5) 0.0176(12) Uani 1 1 d . . .
C11 C 0.4743(6) 0.8356(6) 0.9951(5) 0.0188(12) Uani 1 1 d . . .
H11 H 0.4064 0.8460 0.9459 0.023 Uiso 1 1 d R . .
C12 C 0.4422(6) 0.8031(6) 1.0881(5) 0.0199(13) Uani 1 1 d . . .
H12 H 0.3531 0.7908 1.1028 0.024 Uiso 1 1 d R . .
C13 C 0.6117(7) 0.6438(6) 1.5581(5) 0.0206(13) Uani 1 1 d . . .
C14 C 0.7555(8) 0.6000(7) 1.6844(6) 0.0314(17) Uani 1 1 d . . .
H14 H 0.8422 0.5903 1.7101 0.038 Uiso 1 1 d R . .
C15 C 0.6536(8) 0.5807(6) 1.7438(5) 0.0256(15) Uani 1 1 d . . .
C16 C 0.5270(8) 0.5955(7) 1.7049(6) 0.0268(15) Uani 1 1 d . . .
H16 H 0.4551 0.5836 1.7449 0.032 Uiso 1 1 d R . .
C17 C 0.6395(6) 0.8866(6) 0.8725(5) 0.0167(12) Uani 1 1 d . . .
C18 C 0.7967(7) 0.9403(7) 0.7689(6) 0.0286(16) Uani 1 1 d . . .
H18 H 0.8863 0.9575 0.7568 0.034 Uiso 1 1 d R . .
C19 C 0.7020(7) 0.9483(6) 0.6933(5) 0.0240(14) Uani 1 1 d . . .
C20 C 0.5729(7) 0.9207(7) 0.7127(6) 0.0278(15) Uani 1 1 d . . .
H20 H 0.5056 0.9238 0.6613 0.033 Uiso 1 1 d R . .
C21 C 0.7671(6) 0.7886(6) 1.2290(5) 0.0156(12) Uani 1 1 d . . .
C22 C 0.8654(7) 0.6936(6) 1.2060(5) 0.0206(13) Uani 1 1 d . . .
H22A H 0.9253 0.7273 1.1580 0.027 Uiso 1 1 d R . .
H22B H 0.9191 0.6828 1.2678 0.027 Uiso 1 1 d R . .
C23 C 0.8039(7) 0.5683(6) 1.1639(5) 0.0227(14) Uani 1 1 d . . .
H23A H 0.7487 0.5778 1.1025 0.029 Uiso 1 1 d R . .
H23B H 0.7467 0.5318 1.2124 0.029 Uiso 1 1 d R . .
C24 C 0.9096(7) 0.4825(6) 1.1408(5) 0.0218(13) Uani 1 1 d . . .
H24A H 0.9672 0.5206 1.0934 0.028 Uiso 1 1 d R . .
H24B H 0.9642 0.4736 1.2027 0.028 Uiso 1 1 d R . .
C25 C 0.8553(7) 0.3565(6) 1.0979(6) 0.0265(15) Uani 1 1 d . . .
H25A H 0.8053 0.3644 1.0338 0.035 Uiso 1 1 d R . .
H25B H 0.7938 0.3197 1.1434 0.035 Uiso 1 1 d R . .
C26 C 0.9629(7) 0.2712(6) 1.0814(6) 0.0282(15) Uani 1 1 d . . .
H26A H 1.0239 0.3079 1.0355 0.037 Uiso 1 1 d R . .
H26B H 1.0135 0.2642 1.1454 0.037 Uiso 1 1 d R . .
C27 C 0.9098(8) 0.1440(7) 1.0391(8) 0.041(2) Uani 1 1 d . . .
H27A H 0.9828 0.0938 1.0303 0.06(2) Uiso 1 1 d R . .
H27B H 0.8614 0.1499 0.9749 0.06(2) Uiso 1 1 d R . .
H27C H 0.8508 0.1063 1.0849 0.06(2) Uiso 1 1 d R . .
C28 C 0.8490(6) 0.9107(6) 1.2681(5) 0.0193(13) Uani 1 1 d . . .
H28A H 0.9063 0.8942 1.3267 0.025 Uiso 1 1 d R . .
H28B H 0.9066 0.9372 1.2162 0.025 Uiso 1 1 d R . .
C29 C 0.7691(6) 1.0165(6) 1.2972(5) 0.0197(13) Uani 1 1 d . . .
H29A H 0.7162 1.0380 1.2379 0.026 Uiso 1 1 d R . .
H29B H 0.7079 0.9897 1.3466 0.026 Uiso 1 1 d R . .
C30 C 0.8557(7) 1.1297(6) 1.3404(5) 0.0228(14) Uani 1 1 d . . .
H30A H 0.9158 1.1577 1.2906 0.030 Uiso 1 1 d R . .
H30B H 0.9097 1.1082 1.3991 0.030 Uiso 1 1 d R . .
C31 C 0.7736(7) 1.2338(6) 1.3707(5) 0.0229(14) Uani 1 1 d . . .
H31A H 0.7105 1.2035 1.4177 0.030 Uiso 1 1 d R . .
H31B H 0.7223 1.2565 1.3111 0.030 Uiso 1 1 d R . .
C32 C 0.8543(8) 1.3490(7) 1.4191(6) 0.0307(16) Uani 1 1 d . . .
H32A H 0.9211 1.3765 1.3738 0.040 Uiso 1 1 d R . .
H32B H 0.7954 1.4148 1.4272 0.040 Uiso 1 1 d R . .
C33 C 0.9230(8) 1.3309(7) 1.5194(6) 0.0324(17) Uani 1 1 d . . .
H33A H 0.9729 1.4076 1.5453 0.038(15) Uiso 1 1 d R . .
H33B H 0.9829 1.2670 1.5120 0.038(15) Uiso 1 1 d R . .
H33C H 0.8576 1.3064 1.5655 0.038(15) Uiso 1 1 d R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 0.00 0.0500
1.00 0.00 0.00 0.0500
-1.00 -1.00 0.00 0.1000
1.00 1.00 0.00 0.1000
0.00 1.00 -3.00 0.2000
0.00 -1.00 -3.00 0.2100
0.00 1.00 2.00 0.1800
0.00 0.00 1.00 0.2000
1.00 -1.00 0.00 0.1000
-1.00 1.00 0.00 0.1000
0.00 0.00 -1.00 0.2100
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N1 C14 117.0(7) . . ?
C16 N2 C13 117.6(6) . . ?
C18 N3 C17 117.4(6) . . ?
C20 N4 C17 117.1(6) . . ?
C6 C1 C2 120.8(6) . . ?
C6 C1 C7 131.4(6) . . ?
C2 C1 C7 107.8(6) . . ?
C3 C2 C1 120.3(6) . . ?
C3 C2 C21 128.5(6) . . ?
C1 C2 C21 111.1(6) . . ?
C2 C3 C4 119.6(6) . . ?
C5 C4 C3 119.3(6) . . ?
C5 C4 C13 120.0(6) . . ?
C3 C4 C13 120.7(6) . . ?
C6 C5 C4 121.5(6) . . ?
C5 C6 C1 118.5(6) . . ?
C12 C7 C8 120.1(6) . . ?
C12 C7 C1 130.7(6) . . ?
C8 C7 C1 109.2(5) . . ?
C9 C8 C7 120.8(6) . . ?
C9 C8 C21 129.0(6) . . ?
C7 C8 C21 110.2(5) . . ?
C8 C9 C10 119.6(6) . . ?
C11 C10 C9 119.5(6) . . ?
C11 C10 C17 120.6(6) . . ?
C9 C10 C17 119.8(6) . . ?
C12 C11 C10 120.9(6) . . ?
C11 C12 C7 118.9(6) . . ?
N1 C13 N2 125.3(7) . . ?
N1 C13 C4 117.6(6) . . ?
N2 C13 C4 117.1(6) . . ?
N1 C14 C15 121.4(7) . . ?
C14 C15 C16 118.5(7) . . ?
C14 C15 Br1 121.8(6) . . ?
C16 C15 Br1 119.7(6) . . ?
N2 C16 C15 120.3(7) . . ?
N3 C17 N4 124.8(6) . . ?
N3 C17 C10 117.3(6) . . ?
N4 C17 C10 117.9(6) . . ?
N3 C18 C19 121.9(7) . . ?
C18 C19 C20 117.7(7) . . ?
C18 C19 Br2 121.3(6) . . ?
C20 C19 Br2 121.0(6) . . ?
N4 C20 C19 121.2(7) . . ?
C2 C21 C8 101.4(5) . . ?
C2 C21 C22 113.5(5) . . ?
C8 C21 C22 112.5(5) . . ?
C2 C21 C28 111.2(5) . . ?
C8 C21 C28 110.8(5) . . ?
C22 C21 C28 107.4(5) . . ?
C23 C22 C21 115.4(6) . . ?
C22 C23 C24 111.2(6) . . ?
C25 C24 C23 114.0(6) . . ?
C24 C25 C26 112.6(6) . . ?
C27 C26 C25 113.2(6) . . ?
C29 C28 C21 115.6(5) . . ?
C30 C29 C28 112.4(5) . . ?
C29 C30 C31 111.5(6) . . ?
C30 C31 C32 114.4(6) . . ?
C33 C32 C31 114.1(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C15 1.887(7) . ?
Br2 C19 1.891(7) . ?
N1 C13 1.329(9) . ?
N1 C14 1.344(10) . ?
N2 C16 1.333(9) . ?
N2 C13 1.346(9) . ?
N3 C18 1.321(10) . ?
N3 C17 1.334(9) . ?
N4 C20 1.335(10) . ?
N4 C17 1.341(8) . ?
C1 C6 1.396(9) . ?
C1 C2 1.414(9) . ?
C1 C7 1.466(9) . ?
C2 C3 1.378(9) . ?
C2 C21 1.519(9) . ?
C3 C4 1.410(9) . ?
C4 C5 1.410(9) . ?
C4 C13 1.483(9) . ?
C5 C6 1.386(9) . ?
C7 C12 1.399(9) . ?
C7 C8 1.407(9) . ?
C8 C9 1.361(9) . ?
C8 C21 1.532(9) . ?
C9 C10 1.409(9) . ?
C10 C11 1.403(9) . ?
C10 C17 1.475(9) . ?
C11 C12 1.380(9) . ?
C14 C15 1.370(11) . ?
C15 C16 1.392(11) . ?
C18 C19 1.372(10) . ?
C19 C20 1.377(11) . ?
C21 C22 1.547(9) . ?
C21 C28 1.561(9) . ?
C22 C23 1.522(9) . ?
C23 C24 1.534(9) . ?
C24 C25 1.510(10) . ?
C25 C26 1.528(10) . ?
C26 C27 1.517(10) . ?
C28 C29 1.528(9) . ?
C29 C30 1.522(9) . ?
C30 C31 1.533(9) . ?
C31 C32 1.533(10) . ?
C32 C33 1.516(12) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C27 C26 C25 C24 179.5(7) . . . . ?
C26 C25 C24 C23 -176.7(6) . . . . ?
C25 C24 C23 C22 -179.5(6) . . . . ?
C24 C23 C22 C21 178.3(6) . . . . ?
C23 C22 C21 C28 -178.4(6) . . . . ?
C22 C21 C28 C29 -178.9(5) . . . . ?
C21 C28 C29 C30 176.5(6) . . . . ?
C28 C29 C30 C31 -179.0(6) . . . . ?
C29 C30 C31 C32 177.5(6) . . . . ?
C30 C31 C32 C33 -66.6(9) . . . . ?
C9 C10 C17 N3 -2.9(9) . . . . ?
C3 C4 C13 N1 -3.7(9) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9181979
