#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/64/1506400.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_1506400
loop_
_publ_author_name
'Kee, Hooi Ling'
'Kirmaier, Christine'
'Yu, Lianhe'
'Thamyongkit, Patchanita'
'Youngblood, W. Justin'
'Calder, Matthew E.'
'Ramos, Lavoisier'
'Noll, Bruce C.'
'Bocian, David F.'
'Scheidt, W. Robert'
'Birge, Robert R.'
'Lindsey, Jonathan S.'
'Holten, Dewey'
_publ_section_title
;
 Structural control of the photodynamics of boron-dipyrrin complexes.
;
_journal_issue                   43
_journal_name_full               'The journal of physical chemistry. B'
_journal_page_first              20433
_journal_page_last               20443
_journal_paper_doi               10.1021/jp0525078
_journal_volume                  109
_journal_year                    2005
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C15 H11 B F2 N2'
_chemical_formula_sum            'C15 H11 B F2 N2'
_chemical_formula_weight         268.07
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.559(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2841(2)
_cell_length_b                   20.7345(3)
_cell_length_c                   9.9453(2)
_cell_measurement_reflns_used    4825
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      39.95
_cell_measurement_theta_min      2.88
_cell_volume                     1259.73(5)
_computing_cell_refinement       'Bruker SMART/SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT/SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            16537
_diffrn_reflns_theta_full        40.03
_diffrn_reflns_theta_max         40.03
_diffrn_reflns_theta_min         1.96
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Siemens KFFMO2K-90'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9867
_exptl_absorpt_correction_T_min  0.9459
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'triangular plate'
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.833
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         3877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0521
_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)+(0.1018P)²+0.2800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.1588
_reflns_number_gt                3197
_reflns_number_total             3877
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp0525078si20050512_100656.cif
_cod_data_source_block           bcn33
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1506400
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 0.0000 0.20114(5) 0.7500 0.0324(3) Uani 1 2 d S
F1 F 0.06119(14) 0.23922(4) 0.65146(9) 0.0739(3) Uani 1 1 d .
N1 N 0.19190(9) 0.15643(3) 0.81870(5) 0.01972(11) Uani 1 1 d .
C1 C 0.39048(11) 0.17470(4) 0.89254(7) 0.02543(13) Uani 1 1 d .
H1 H 0.4357 0.2181 0.9115 0.031 Uiso 1 1 calc R
C2 C 0.52155(11) 0.12031(4) 0.93768(7) 0.02688(14) Uani 1 1 d .
H2 H 0.6681 0.1203 0.9914 0.032 Uiso 1 1 calc R
C3 C 0.39495(10) 0.06673(4) 0.88845(6) 0.02200(12) Uani 1 1 d .
H3 H 0.4388 0.0229 0.9020 0.026 Uiso 1 1 calc R
C4 C 0.18850(9) 0.08944(3) 0.81438(5) 0.01707(10) Uani 1 1 d .
C5 C 0.0000 0.05559(4) 0.7500 0.01597(12) Uani 1 2 d S
C6 C 0.0000 -0.01585(4) 0.7500 0.01768(13) Uani 1 2 d S
C7 C -0.14529(11) -0.05014(3) 0.81043(7) 0.02233(12) Uani 1 1 d .
H7 H -0.2448 -0.0274 0.8517 0.027 Uiso 1 1 calc R
C8 C -0.14524(12) -0.11729(3) 0.81055(8) 0.02542(14) Uani 1 1 d .
H8 H -0.2443 -0.1402 0.8519 0.031 Uiso 1 1 calc R
C9 C 0.0000 -0.15078(4) 0.7500 0.02496(17) Uani 1 2 d S
H9 H 0.0000 -0.1966 0.7500 0.030 Uiso 1 2 calc SR
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
B1 0.0398(6) 0.0154(4) 0.0330(5) 0.000 -0.0096(4) 0.000
F1 0.0681(5) 0.0522(4) 0.0766(5) 0.0478(4) -0.0330(4) -0.0338(4)
N1 0.0231(2) 0.0179(2) 0.0166(2) 0.00019(13) 0.00145(15) -0.00410(15)
C1 0.0268(3) 0.0300(3) 0.0179(2) -0.00216(19) 0.00217(19) -0.0112(2)
C2 0.0191(2) 0.0417(4) 0.0183(2) -0.0001(2) 0.00127(18) -0.0049(2)
C3 0.0180(2) 0.0299(3) 0.0177(2) 0.00338(18) 0.00349(16) 0.00318(18)
C4 0.0169(2) 0.0178(2) 0.0161(2) 0.00150(14) 0.00304(15) -0.00030(14)
C5 0.0168(3) 0.0152(3) 0.0167(3) 0.000 0.0055(2) 0.000
C6 0.0197(3) 0.0151(3) 0.0203(3) 0.000 0.0088(2) 0.000
C7 0.0255(3) 0.0177(2) 0.0282(3) 0.00214(18) 0.0153(2) 0.00046(17)
C8 0.0313(3) 0.0179(2) 0.0314(3) 0.00360(19) 0.0162(2) -0.00143(19)
C9 0.0335(4) 0.0157(3) 0.0279(4) 0.000 0.0118(3) 0.000
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
F1 B1 F1 110.29(12) . 2_556
F1 B1 N1 110.30(4) . 2_556
F1 B1 N1 109.75(4) 2_556 2_556
F1 B1 N1 109.75(4) . .
F1 B1 N1 110.30(4) 2_556 .
N1 B1 N1 106.39(8) 2_556 .
C1 N1 C4 107.68(5) . .
C1 N1 B1 126.83(6) . .
C4 N1 B1 125.48(5) . .
N1 C1 C2 110.33(6) . .
N1 C1 H1 124.8 . .
C2 C1 H1 124.8 . .
C3 C2 C1 106.56(6) . .
C3 C2 H2 126.7 . .
C1 C2 H2 126.7 . .
C2 C3 C4 107.31(6) . .
C2 C3 H3 126.3 . .
C4 C3 H3 126.3 . .
N1 C4 C5 121.45(5) . .
N1 C4 C3 108.13(5) . .
C5 C4 C3 130.36(6) . .
C4 C5 C4 119.65(7) . 2_556
C4 C5 C6 120.17(4) . .
C4 C5 C6 120.17(4) 2_556 .
C7 C6 C7 118.93(7) 2_556 .
C7 C6 C5 120.53(4) 2_556 .
C7 C6 C5 120.53(4) . .
C8 C7 C6 120.56(6) . .
C8 C7 H7 119.7 . .
C6 C7 H7 119.7 . .
C9 C8 C7 119.92(6) . .
C9 C8 H8 120.0 . .
C7 C8 H8 120.0 . .
C8 C9 C8 120.11(8) . 2_556
C8 C9 H9 119.9 . .
C8 C9 H9 119.9 2_556 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 F1 1.3814(10) .
B1 F1 1.3814(10) 2_556
B1 N1 1.5472(9) 2_556
B1 N1 1.5472(9) .
N1 C1 1.3455(8) .
N1 C4 1.3898(8) .
C1 C2 1.4065(11) .
C1 H1 0.9500 .
C2 C3 1.3871(10) .
C2 H2 0.9500 .
C3 C4 1.4140(8) .
C3 H3 0.9500 .
C4 C5 1.3965(7) .
C5 C4 1.3965(7) 2_556
C5 C6 1.4813(11) .
C6 C7 1.3990(7) 2_556
C6 C7 1.3990(7) .
C7 C8 1.3924(9) .
C7 H7 0.9500 .
C8 C9 1.3913(8) .
C8 H8 0.9500 .
C9 C8 1.3913(8) 2_556
C9 H9 0.9500 .
