#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:24:46 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179842 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/38/7013864.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_7013864
loop_
_publ_author_name
'Klappa, Jamie J.'
'Geers, Sarah A.'
'Schmidtke, Sarah J.'
'MacManus-Spencer, Laura A'
'McNeill, Kristopher'
_publ_section_title
;
 Pyridylpyrrolides as alternatives to cyclometalated phenylpyridine
 ligands: synthesis and characterization of luminescent zinc and boron
 pyridylpyrrolide complexes.
;
_journal_issue                   6
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              883
_journal_page_last               891
_journal_paper_doi               10.1039/b315523d
_journal_year                    2004
_chemical_formula_moiety         'C11 H11 B F2 N2'
_chemical_formula_sum            'C11 H11 B F2 N2'
_chemical_formula_weight         220.03
_chemical_name_common            03064
_chemical_name_systematic
;
?
;
_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                65.793(8)
_cell_angle_beta                 89.589(9)
_cell_angle_gamma                75.611(9)
_cell_formula_units_Z            2
_cell_length_a                   7.145(4)
_cell_length_b                   8.990(5)
_cell_length_c                   9.300(5)
_cell_measurement_reflns_used    1647
_cell_measurement_temperature    173(2)
_cell_volume                     524.7(5)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'SHELXTL, Bruker'
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Siemens SMART Platform CCD'
_diffrn_measurement_method       'area detector, omega 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  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5229
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.887097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         1845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0388
_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/[σ²(Fo²)+(0.0436P)²+0.2140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0950
_reflns_number_gt                1549
_reflns_number_total             1845
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b315523d.txt
_cod_data_source_block           '#6'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7013864
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
B1 B 0.2896(3) 0.8400(2) 0.8286(2) 0.0303(4) Uani 1 1 d . . .
F1 F 0.46429(15) 0.76341(13) 0.79164(12) 0.0445(3) Uani 1 1 d . . .
F2 F 0.14182(16) 0.78685(13) 0.78740(12) 0.0442(3) Uani 1 1 d . . .
N1 N 0.30301(19) 0.79421(16) 1.01553(15) 0.0269(3) Uani 1 1 d . . .
N2 N 0.24718(19) 1.03174(16) 0.77000(15) 0.0276(3) Uani 1 1 d . . .
C1 C 0.3427(2) 0.6385(2) 1.1366(2) 0.0326(4) Uani 1 1 d . . .
H1 H 0.366(3) 0.543(2) 1.107(2) 0.039 Uiso 1 1 d . . .
C2 C 0.3461(3) 0.6195(2) 1.2903(2) 0.0375(4) Uani 1 1 d . . .
H2 H 0.376(3) 0.505(3) 1.376(2) 0.045 Uiso 1 1 d . . .
C3 C 0.3074(3) 0.7631(2) 1.3201(2) 0.0380(4) Uani 1 1 d . . .
H3 H 0.310(3) 0.754(2) 1.428(2) 0.046 Uiso 1 1 d . . .
C4 C 0.2684(2) 0.9227(2) 1.1972(2) 0.0326(4) Uani 1 1 d . . .
H4 H 0.241(3) 1.028(2) 1.213(2) 0.039 Uiso 1 1 d . . .
C5 C 0.2674(2) 0.9365(2) 1.04196(19) 0.0266(4) Uani 1 1 d . . .
C6 C 0.2331(2) 1.0824(2) 0.89269(18) 0.0262(4) Uani 1 1 d . . .
C7 C 0.1884(2) 1.2577(2) 0.83097(19) 0.0287(4) Uani 1 1 d . . .
C8 C 0.1758(2) 1.3123(2) 0.6648(2) 0.0309(4) Uani 1 1 d . . .
H8 H 0.145(3) 1.426(2) 0.589(2) 0.037 Uiso 1 1 d . . .
C9 C 0.2107(2) 1.1731(2) 0.63023(19) 0.0297(4) Uani 1 1 d . . .
C10 C 0.2108(3) 1.1615(3) 0.4741(2) 0.0425(5) Uani 1 1 d . . .
H10A H 0.2396 1.0424 0.4922 0.064 Uiso 0.50 1 calc PR . .
H10B H 0.3101 1.2115 0.4145 0.064 Uiso 0.50 1 calc PR . .
H10C H 0.0829 1.2231 0.4133 0.064 Uiso 0.50 1 calc PR . .
H10D H 0.1821 1.2756 0.3878 0.064 Uiso 0.50 1 calc PR . .
H10E H 0.1116 1.1065 0.4656 0.064 Uiso 0.50 1 calc PR . .
H10F H 0.3388 1.0949 0.4667 0.064 Uiso 0.50 1 calc PR . .
C11 C 0.1570(3) 1.3676(2) 0.9187(2) 0.0368(4) Uani 1 1 d . . .
H11A H 0.1289 1.4867 0.8426 0.055 Uiso 0.50 1 calc PR . .
H11B H 0.2744 1.3382 0.9894 0.055 Uiso 0.50 1 calc PR . .
H11C H 0.0472 1.3500 0.9814 0.055 Uiso 0.50 1 calc PR . .
H11D H 0.1714 1.2966 1.0329 0.055 Uiso 0.50 1 calc PR . .
H11E H 0.0260 1.4451 0.8862 0.055 Uiso 0.50 1 calc PR . .
H11F H 0.2531 1.4333 0.8942 0.055 Uiso 0.50 1 calc PR . .
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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
F2 B1 F1 109.98(15) . . ?
F2 B1 N2 114.47(15) . . ?
F1 B1 N2 114.77(14) . . ?
F2 B1 N1 110.11(14) . . ?
F1 B1 N1 109.81(14) . . ?
N2 B1 N1 96.93(12) . . ?
C1 N1 C5 121.46(15) . . ?
C1 N1 B1 127.17(14) . . ?
C5 N1 B1 111.37(13) . . ?
C9 N2 C6 108.15(14) . . ?
C9 N2 B1 139.01(14) . . ?
C6 N2 B1 112.78(13) . . ?
N1 C1 C2 120.50(17) . . ?
N1 C1 H1 116.2(11) . . ?
C2 C1 H1 123.3(11) . . ?
C1 C2 C3 119.05(17) . . ?
C1 C2 H2 118.8(11) . . ?
C3 C2 H2 122.2(11) . . ?
C4 C3 C2 120.87(18) . . ?
C4 C3 H3 118.0(11) . . ?
C2 C3 H3 121.1(11) . . ?
C3 C4 C5 118.31(17) . . ?
C3 C4 H4 123.6(11) . . ?
C5 C4 H4 118.1(11) . . ?
N1 C5 C4 119.80(15) . . ?
N1 C5 C6 109.24(14) . . ?
C4 C5 C6 130.97(15) . . ?
N2 C6 C7 109.67(14) . . ?
N2 C6 C5 109.65(14) . . ?
C7 C6 C5 140.68(15) . . ?
C6 C7 C8 104.92(14) . . ?
C6 C7 C11 128.33(15) . . ?
C8 C7 C11 126.74(15) . . ?
C9 C8 C7 109.30(15) . . ?
C9 C8 H8 124.9(11) . . ?
C7 C8 H8 125.8(11) . . ?
N2 C9 C8 107.95(15) . . ?
N2 C9 C10 121.39(16) . . ?
C8 C9 C10 130.65(16) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C10 H10D 109.5 . . ?
H10A C10 H10D 141.1 . . ?
H10B C10 H10D 56.3 . . ?
H10C C10 H10D 56.3 . . ?
C9 C10 H10E 109.5 . . ?
H10A C10 H10E 56.3 . . ?
H10B C10 H10E 141.1 . . ?
H10C C10 H10E 56.3 . . ?
H10D C10 H10E 109.5 . . ?
C9 C10 H10F 109.5 . . ?
H10A C10 H10F 56.3 . . ?
H10B C10 H10F 56.3 . . ?
H10C C10 H10F 141.1 . . ?
H10D C10 H10F 109.5 . . ?
H10E C10 H10F 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C11 H11D 109.5 . . ?
H11A C11 H11D 141.1 . . ?
H11B C11 H11D 56.3 . . ?
H11C C11 H11D 56.3 . . ?
C7 C11 H11E 109.5 . . ?
H11A C11 H11E 56.3 . . ?
H11B C11 H11E 141.1 . . ?
H11C C11 H11E 56.3 . . ?
H11D C11 H11E 109.5 . . ?
C7 C11 H11F 109.5 . . ?
H11A C11 H11F 56.3 . . ?
H11B C11 H11F 56.3 . . ?
H11C C11 H11F 141.1 . . ?
H11D C11 H11F 109.5 . . ?
H11E C11 H11F 109.5 . . ?
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
B1 F2 1.377(2) . ?
B1 F1 1.382(2) . ?
B1 N2 1.527(2) . ?
B1 N1 1.612(2) . ?
N1 C1 1.350(2) . ?
N1 C5 1.363(2) . ?
N2 C9 1.363(2) . ?
N2 C6 1.386(2) . ?
C1 C2 1.368(3) . ?
C1 H1 0.984(19) . ?
C2 C3 1.391(3) . ?
C2 H2 0.98(2) . ?
C3 C4 1.379(3) . ?
C3 H3 0.97(2) . ?
C4 C5 1.398(2) . ?
C4 H4 0.985(19) . ?
C5 C6 1.435(2) . ?
C6 C7 1.387(2) . ?
C7 C8 1.413(3) . ?
C7 C11 1.497(2) . ?
C8 C9 1.380(3) . ?
C8 H8 0.944(19) . ?
C9 C10 1.498(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 H10D 0.9800 . ?
C10 H10E 0.9800 . ?
C10 H10F 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 H11D 0.9800 . ?
C11 H11E 0.9800 . ?
C11 H11F 0.9800 . ?
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
F2 B1 N1 C1 62.2(2) . . . . ?
F1 B1 N1 C1 -59.0(2) . . . . ?
N2 B1 N1 C1 -178.53(14) . . . . ?
F2 B1 N1 C5 -117.50(15) . . . . ?
F1 B1 N1 C5 121.25(15) . . . . ?
N2 B1 N1 C5 1.76(16) . . . . ?
F2 B1 N2 C9 -62.6(3) . . . . ?
F1 B1 N2 C9 66.0(3) . . . . ?
N1 B1 N2 C9 -178.44(17) . . . . ?
F2 B1 N2 C6 114.07(16) . . . . ?
F1 B1 N2 C6 -117.37(16) . . . . ?
N1 B1 N2 C6 -1.77(16) . . . . ?
C5 N1 C1 C2 0.7(2) . . . . ?
B1 N1 C1 C2 -178.94(16) . . . . ?
N1 C1 C2 C3 0.2(3) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C1 N1 C5 C4 -1.1(2) . . . . ?
B1 N1 C5 C4 178.62(14) . . . . ?
C1 N1 C5 C6 179.08(13) . . . . ?
B1 N1 C5 C6 -1.19(17) . . . . ?
C3 C4 C5 N1 0.5(2) . . . . ?
C3 C4 C5 C6 -179.73(16) . . . . ?
C9 N2 C6 C7 -0.39(17) . . . . ?
B1 N2 C6 C7 -178.10(14) . . . . ?
C9 N2 C6 C5 179.00(13) . . . . ?
B1 N2 C6 C5 1.29(17) . . . . ?
N1 C5 C6 N2 -0.02(17) . . . . ?
C4 C5 C6 N2 -179.79(16) . . . . ?
N1 C5 C6 C7 179.08(19) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
N2 C6 C7 C8 -0.01(17) . . . . ?
C5 C6 C7 C8 -179.11(19) . . . . ?
N2 C6 C7 C11 179.19(16) . . . . ?
C5 C6 C7 C11 0.1(3) . . . . ?
C6 C7 C8 C9 0.41(18) . . . . ?
C11 C7 C8 C9 -178.81(16) . . . . ?
C6 N2 C9 C8 0.64(18) . . . . ?
B1 N2 C9 C8 177.42(18) . . . . ?
C6 N2 C9 C10 -178.78(15) . . . . ?
B1 N2 C9 C10 -2.0(3) . . . . ?
C7 C8 C9 N2 -0.66(19) . . . . ?
C7 C8 C9 C10 178.69(17) . . . . ?
