#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/32/1513275.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1513275
loop_
_publ_author_name
'Meng, Ge'
'Velayudham, Singaravelu'
'Smith, Adrian'
'Luck, Rudy'
'Liu, Haiying'
_publ_section_title
;
 Color Tuning of Polyfluorene Emission with BODIPY Monomers
;
_journal_issue                   6
_journal_name_full               Macromolecules
_journal_page_first              1995
_journal_paper_doi               10.1021/ma8023975
_journal_volume                  42
_journal_year                    2009
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C21 H23 B1 F2 N2'
_chemical_formula_sum            'C21 H23 B F2 N2'
_chemical_formula_weight         352.24
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2008-12-18T14:26:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 112.49(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.442(5)
_cell_length_b                   7.847(2)
_cell_length_c                   25.831(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_measurement_wavelength     0.71073
_cell_volume                     3828.4(19)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_orient_matrix_type
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      -0.034973
_diffrn_orient_matrix_UB_12      -0.017479
_diffrn_orient_matrix_UB_13      -0.039159
_diffrn_orient_matrix_UB_21      -0.038401
_diffrn_orient_matrix_UB_22      0.047284
_diffrn_orient_matrix_UB_23      0.010834
_diffrn_orient_matrix_UB_31      0.010262
_diffrn_orient_matrix_UB_32      0.117049
_diffrn_orient_matrix_UB_33      -0.010235
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            2580
_diffrn_reflns_theta_full        22.47
_diffrn_reflns_theta_max         22.47
_diffrn_reflns_theta_min         1.71
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  166
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9662
_exptl_absorpt_correction_T_min  0.9411
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
        Number of psi-scan sets used was   9
        Theta correction was applied.
        Averaged transmission function was used.
        No Fourier smoothing was applied.
;
_exptl_crystal_colour            gold
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0075(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2496
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.067
_refine_ls_R_factor_gt           0.0587
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1040P)²+6.7104P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1806
_refine_ls_wR_factor_ref         0.1899
_reflns_number_gt                2166
_reflns_number_total             2496
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ma8023975sup1.cif
_cod_data_source_block           gemeng
_cod_original_cell_volume        3828.4(18)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C21 H23 B1 F2 N2'
_cod_database_code               1513275
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
B1 B 0.13541(18) 0.4121(6) 0.41978(15) 0.0601(10) Uani 1 1 d .
F1 F 0.17681(10) 0.4616(3) 0.47419(8) 0.0855(8) Uani 1 1 d .
F2 F 0.17766(11) 0.3320(3) 0.39607(10) 0.0902(8) Uani 1 1 d .
N1 N 0.09920(13) 0.5689(4) 0.38504(11) 0.0566(8) Uani 1 1 d .
N2 N 0.07610(12) 0.2904(4) 0.42025(10) 0.0526(7) Uani 1 1 d .
C1 C 0.2112(2) 0.7168(7) 0.3929(2) 0.0951(14) Uani 1 1 d .
H1A H 0.2325 0.6151 0.4129 0.143 Uiso 1 1 calc R
H1B H 0.2281 0.8138 0.417 0.143 Uiso 1 1 calc R
H1C H 0.2234 0.7292 0.3607 0.143 Uiso 1 1 calc R
C2 C 0.13204(18) 0.7049(5) 0.37425(15) 0.0671(10) Uani 1 1 d .
C3 C 0.0812(2) 0.8232(5) 0.34411(15) 0.0704(10) Uani 1 1 d .
H3 H 0.0905 0.9282 0.3317 0.085 Uiso 1 1 calc R
C4 C 0.01461(17) 0.7611(4) 0.33541(13) 0.0581(9) Uani 1 1 d .
C5 C -0.0541(2) 0.8522(5) 0.30470(15) 0.0711(10) Uani 1 1 d .
H5A H -0.0928 0.7821 0.3042 0.107 Uiso 1 1 calc R
H5B H -0.0587 0.8748 0.2669 0.107 Uiso 1 1 calc R
H5C H -0.0546 0.9577 0.3233 0.107 Uiso 1 1 calc R
C6 C 0.02565(15) 0.5989(4) 0.36146(12) 0.0503(8) Uani 1 1 d .
C7 C -0.02123(14) 0.4774(4) 0.36679(11) 0.0465(8) Uani 1 1 d .
C8 C 0.15555(19) 0.0579(5) 0.47619(16) 0.0792(12) Uani 1 1 d .
H8A H 0.1919 0.1319 0.4742 0.119 Uiso 1 1 calc R
H8B H 0.1581 -0.0499 0.4595 0.119 Uiso 1 1 calc R
H8C H 0.1621 0.0411 0.5147 0.119 Uiso 1 1 calc R
C9 C 0.08489(18) 0.1367(5) 0.44538(13) 0.0595(9) Uani 1 1 d .
C10 C 0.01838(18) 0.0720(5) 0.43794(14) 0.0637(9) Uani 1 1 d .
H10 H 0.0102 -0.0322 0.4516 0.076 Uiso 1 1 calc R
C11 C -0.03331(16) 0.1849(4) 0.40754(13) 0.0536(8) Uani 1 1 d .
C12 C -0.11134(18) 0.1603(5) 0.39158(18) 0.0725(10) Uani 1 1 d .
H12A H -0.1363 0.2571 0.3705 0.109 Uiso 1 1 calc R
H12B H -0.1213 0.1486 0.4248 0.109 Uiso 1 1 calc R
H12C H -0.1263 0.0593 0.3691 0.109 Uiso 1 1 calc R
C13 C 0.00298(15) 0.3249(4) 0.39578(12) 0.0487(8) Uani 1 1 d .
C14 C -0.09933(15) 0.5096(4) 0.34062(13) 0.0497(8) Uani 1 1 d .
C15 C -0.13389(18) 0.5804(4) 0.37298(15) 0.0619(9) Uani 1 1 d .
C16 C -0.2072(2) 0.6078(5) 0.3467(2) 0.0834(13) Uani 1 1 d .
H16 H -0.2316 0.656 0.367 0.1 Uiso 1 1 calc R
C17 C -0.2433(2) 0.5647(6) 0.2918(2) 0.0942(15) Uani 1 1 d .
H17 H -0.292 0.5822 0.2754 0.113 Uiso 1 1 calc R
C18 C -0.20863(19) 0.4958(5) 0.26064(18) 0.0782(11) Uani 1 1 d .
H18 H -0.234 0.4677 0.2233 0.094 Uiso 1 1 calc R
C19 C -0.13638(16) 0.4678(4) 0.28403(14) 0.0574(9) Uani 1 1 d .
C20 C -0.0987(2) 0.3937(6) 0.24940(15) 0.0768(11) Uani 1 1 d .
H20A H -0.0492 0.3828 0.272 0.115 Uiso 1 1 calc R
H20B H -0.1049 0.4674 0.2182 0.115 Uiso 1 1 calc R
H20C H -0.1181 0.2834 0.2358 0.115 Uiso 1 1 calc R
C21 C -0.0942(2) 0.6236(6) 0.43371(17) 0.0851(13) Uani 1 1 d .
H21A H -0.1264 0.6707 0.4489 0.128 Uiso 1 1 calc R
H21B H -0.058 0.7055 0.437 0.128 Uiso 1 1 calc R
H21C H -0.073 0.5223 0.454 0.128 Uiso 1 1 calc 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 3 8
-3 5 4
0 4 -1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
F2 B1 F1 109.4(3)
F2 B1 N1 110.3(3)
F1 B1 N1 109.8(3)
F2 B1 N2 110.2(3)
F1 B1 N2 109.9(3)
N1 B1 N2 107.2(3)
C2 N1 C6 108.2(3)
C2 N1 B1 126.1(3)
C6 N1 B1 125.6(3)
C9 N2 C13 108.1(3)
C9 N2 B1 126.5(3)
C13 N2 B1 125.3(3)
N1 C2 C3 108.7(3)
N1 C2 C1 122.9(4)
C3 C2 C1 128.4(4)
C4 C3 C2 109.6(3)
C3 C4 C6 105.8(3)
C3 C4 C5 125.6(3)
C6 C4 C5 128.7(3)
C7 C6 N1 120.2(3)
C7 C6 C4 132.1(3)
N1 C6 C4 107.8(3)
C6 C7 C13 121.5(3)
C6 C7 C14 119.6(3)
C13 C7 C14 119.0(3)
N2 C9 C10 108.4(3)
N2 C9 C8 123.5(3)
C10 C9 C8 128.1(3)
C11 C10 C9 109.9(3)
C10 C11 C13 105.7(3)
C10 C11 C12 125.4(3)
C13 C11 C12 128.9(3)
C7 C13 N2 120.2(3)
C7 C13 C11 132.0(3)
N2 C13 C11 107.8(3)
C15 C14 C19 121.3(3)
C15 C14 C7 119.5(3)
C19 C14 C7 119.2(3)
C14 C15 C16 117.5(4)
C14 C15 C21 121.3(3)
C16 C15 C21 121.3(3)
C17 C16 C15 121.1(4)
C16 C17 C18 120.7(4)
C17 C18 C19 120.8(4)
C18 C19 C14 118.6(3)
C18 C19 C20 120.4(3)
C14 C19 C20 121.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
B1 F2 1.386(4)
B1 F1 1.390(4)
B1 N1 1.535(5)
B1 N2 1.547(5)
N1 C2 1.346(4)
N1 C6 1.409(4)
N2 C9 1.349(4)
N2 C13 1.409(4)
C1 C2 1.503(5)
C2 C3 1.389(5)
C3 C4 1.380(5)
C4 C6 1.417(5)
C4 C5 1.503(5)
C6 C7 1.396(4)
C7 C13 1.397(4)
C7 C14 1.498(4)
C8 C9 1.491(5)
C9 C10 1.394(5)
C10 C11 1.373(5)
C11 C13 1.422(4)
C11 C12 1.499(4)
C14 C15 1.399(4)
C14 C19 1.404(4)
C15 C16 1.406(5)
C15 C21 1.503(5)
C16 C17 1.367(6)
C17 C18 1.371(7)
C18 C19 1.383(5)
C19 C20 1.502(5)
