#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:59:43 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179874 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/70/7017067.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_7017067
loop_
_publ_author_name
'Zhong, Yihan'
'Si, Liping'
'He, Hongshan'
'Sykes, Andrew G.'
_publ_section_title
;
 BODIPY chromophores as efficient green light sensitizers for
 lanthanide-induced near-infrared emission.
;
_journal_issue                   43
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11389
_journal_page_last               11395
_journal_paper_doi               10.1039/c1dt11137j
_journal_volume                  40
_journal_year                    2011
_chemical_formula_moiety         'C15 H15 B F2'
_chemical_formula_sum            'C15 H15 B F2'
_chemical_formula_weight         244.08
_chemical_name_common            BODIPY
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 107.0770(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6854(7)
_cell_length_b                   14.2972(14)
_cell_length_c                   11.4501(11)
_cell_measurement_reflns_used    5889
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.45
_cell_measurement_theta_min      2.34
_cell_volume                     1202.7(2)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2006)'
_computing_data_collection       'Bruker APEXII (Bruker, 2006)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2006)'
_computing_molecular_graphics    'Ortep-3(Farrugia, 1997)'
_computing_publication_material  'WinGX(Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997a)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11441
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_correction_T_min  0.9441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0706
_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)+(0.1224P)²+2.4202P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2039
_refine_ls_wR_factor_ref         0.2173
_reflns_number_gt                1759
_reflns_number_total             2104
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1dt11137j.txt
_cod_data_source_block           09053
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7017067
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.7157(5) 0.2270(2) 0.8827(3) 0.0282(8) Uani 1 1 d .
H1A H 0.7413 0.2312 0.8040 0.042 Uiso 1 1 calc R
H1B H 0.5867 0.2123 0.8690 0.042 Uiso 1 1 calc R
H1C H 0.7906 0.1776 0.9322 0.042 Uiso 1 1 calc R
C2 C 0.7589(4) 0.3183(2) 0.9482(3) 0.0242(7) Uani 1 1 d .
C3 C 0.8838(4) 0.3351(2) 1.0633(3) 0.0254(7) Uani 1 1 d .
H3 H 0.9597 0.2898 1.1145 0.030 Uiso 1 1 calc R
C4 C 0.8767(4) 0.4305(2) 1.0890(3) 0.0229(7) Uani 1 1 d .
C5 C 0.9836(4) 0.4817(2) 1.2006(3) 0.0276(8) Uani 1 1 d .
H5A H 0.9498 0.5480 1.1930 0.041 Uiso 1 1 calc R
H5B H 1.1138 0.4754 1.2096 0.041 Uiso 1 1 calc R
H5C H 0.9573 0.4552 1.2726 0.041 Uiso 1 1 calc R
C6 C 0.7454(4) 0.4696(2) 0.9869(3) 0.0216(7) Uani 1 1 d .
C7 C 0.6763(4) 0.39939(18) 0.9017(2) 0.0099(6) Uani 1 1 d .
C8 C 0.6873(4) 0.5614(2) 0.9625(3) 0.0210(7) Uani 1 1 d .
H8 H 0.7349 0.6080 1.0225 0.025 Uiso 1 1 calc R
C9 C 0.5307(5) 0.7659(2) 0.8777(3) 0.0273(8) Uani 1 1 d .
H9A H 0.6186 0.7550 0.9580 0.041 Uiso 1 1 calc R
H9B H 0.4190 0.7927 0.8883 0.041 Uiso 1 1 calc R
H9C H 0.5828 0.8093 0.8309 0.041 Uiso 1 1 calc R
C10 C 0.4876(4) 0.6755(2) 0.8107(3) 0.0227(7) Uani 1 1 d .
C11 C 0.3705(4) 0.6605(2) 0.6946(3) 0.0246(7) Uani 1 1 d .
H11 H 0.2999 0.7071 0.6426 0.030 Uiso 1 1 calc R
C12 C 0.3733(4) 0.5651(2) 0.6666(3) 0.0235(7) Uani 1 1 d .
C13 C 0.2697(5) 0.5160(2) 0.5527(3) 0.0272(8) Uani 1 1 d .
H13A H 0.1947 0.5613 0.4954 0.041 Uiso 1 1 calc R
H13B H 0.1911 0.4683 0.5725 0.041 Uiso 1 1 calc R
H13C H 0.3550 0.4860 0.5154 0.041 Uiso 1 1 calc R
C14 C 0.4891(3) 0.52006(19) 0.7630(2) 0.0105(6) Uani 1 1 d .
C15 C 0.5624(4) 0.5868(2) 0.8538(3) 0.0212(7) Uani 1 1 d .
F1 F 0.3708(2) 0.36448(13) 0.77591(17) 0.0276(5) Uani 1 1 d .
F2 F 0.5909(3) 0.38100(13) 0.68195(16) 0.0285(5) Uani 1 1 d .
B1 B 0.5292(5) 0.4134(3) 0.7767(3) 0.0209(8) Uani 1 1 d .
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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C7 C2 C3 109.6(3)
C7 C2 C1 122.8(3)
C3 C2 C1 127.7(3)
C4 C3 C2 107.8(3)
C4 C3 H3 126.1
C2 C3 H3 126.1
C3 C4 C6 105.9(3)
C3 C4 C5 127.8(3)
C6 C4 C5 126.4(3)
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C8 C6 C7 120.5(3)
C8 C6 C4 130.4(3)
C7 C6 C4 109.0(3)
C2 C7 C6 107.7(3)
C2 C7 B1 127.1(3)
C6 C7 B1 125.2(3)
C15 C8 C6 121.9(3)
C15 C8 H8 119.1
C6 C8 H8 119.1
C10 C9 H9A 109.5
C10 C9 H9B 109.5
H9A C9 H9B 109.5
C10 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C11 C10 C15 106.2(3)
C11 C10 C9 127.7(3)
C15 C10 C9 126.1(3)
C10 C11 C12 108.7(3)
C10 C11 H11 125.7
C12 C11 H11 125.7
C14 C12 C11 109.0(3)
C14 C12 C13 122.8(3)
C11 C12 C13 128.2(3)
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C12 C14 C15 107.7(3)
C12 C14 B1 127.6(3)
C15 C14 B1 124.6(3)
C8 C15 C14 120.8(3)
C8 C15 C10 130.7(3)
C14 C15 C10 108.4(3)
F2 B1 F1 109.0(3)
F2 B1 C7 110.7(3)
F1 B1 C7 109.7(3)
F2 B1 C14 110.6(3)
F1 B1 C14 110.0(3)
C7 B1 C14 106.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.494(4)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C7 1.354(4)
C2 C3 1.404(5)
C3 C4 1.399(5)
C3 H3 0.9500
C4 C6 1.416(4)
C4 C5 1.492(4)
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 C8 1.387(5)
C6 C7 1.392(4)
C7 B1 1.555(4)
C8 C15 1.379(5)
C8 H8 0.9500
C9 C10 1.490(5)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 C11 1.386(5)
C10 C15 1.420(4)
C11 C12 1.402(5)
C11 H11 0.9500
C12 C14 1.360(4)
C12 C13 1.489(4)
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 C15 1.401(4)
C14 B1 1.555(4)
F1 B1 1.401(4)
F2 B1 1.385(4)
