#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:52:57 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180159 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/55/7105559.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_7105559
loop_
_publ_author_name
'Lu, Hua'
'Xue, Zhaoli'
'Mack, John'
'Shen, Zhen'
'You, Xiaozeng'
'Kobayashi, Nagao'
_publ_section_title
;
 Specific Cu2+-induced J-aggregation and Hg2+-induced fluorescence
 enhancement based on BODIPY
;
_journal_issue                   20
_journal_name_full               'Chemical Communications'
_journal_page_first              3565
_journal_paper_doi               10.1039/b926300d
_journal_volume                  46
_journal_year                    2010
_chemical_formula_moiety         'C19 H20 B F2 N3 O'
_chemical_formula_sum            'C19 H20 B F2 N3 O'
_chemical_formula_weight         355.19
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 126.05(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.941(4)
_cell_length_b                   7.683(2)
_cell_length_c                   18.761(3)
_cell_measurement_reflns_used    1123
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.10
_cell_measurement_theta_min      2.18
_cell_volume                     1857.7(9)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXL97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker smart apex II CCD'
_diffrn_measurement_method       'φ and 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  0.1854
_diffrn_reflns_av_sigmaI/netI    0.1687
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8215
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Blok
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.1616
_refine_ls_R_factor_gt           0.0701
_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/[σ^2^(Fo^2^)+(0.0885P)^2] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1613
_refine_ls_wR_factor_ref         0.2172
_reflns_number_gt                1492
_reflns_number_total             3254
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b926300d.txt
_cod_data_source_block           1
_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.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' 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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7105559
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.1347(4) 0.4488(6) 0.1896(4) 0.0292(13) Uani 1 1 d . . .
C1 C 0.4193(4) 0.5550(6) 0.5386(3) 0.0351(12) Uani 1 1 d . . .
H1 H 0.4400 0.4596 0.5219 0.042 Uiso 1 1 calc R . .
C2 C 0.4813(4) 0.6108(6) 0.6284(3) 0.0356(12) Uani 1 1 d . . .
C3 C 0.4485(4) 0.7525(6) 0.6545(3) 0.0408(13) Uani 1 1 d . . .
C4 C 0.3565(4) 0.8424(6) 0.5921(3) 0.0435(14) Uani 1 1 d . . .
H4 H 0.3353 0.9362 0.6092 0.052 Uiso 1 1 calc R . .
C5 C 0.2962(4) 0.7878(6) 0.5023(3) 0.0367(12) Uani 1 1 d . . .
H5 H 0.2357 0.8480 0.4610 0.044 Uiso 1 1 calc R . .
C6 C 0.3260(4) 0.6442(5) 0.4744(3) 0.0302(11) Uani 1 1 d . . .
C7 C 0.2591(4) 0.5836(5) 0.3794(3) 0.0268(11) Uani 1 1 d . . .
C8 C 0.2487(4) 0.6929(5) 0.3118(3) 0.0275(11) Uani 1 1 d . . .
C9 C 0.3755(4) 0.9690(6) 0.3944(3) 0.0422(13) Uani 1 1 d . . .
H9A H 0.4108 1.0417 0.3782 0.063 Uiso 1 1 d R . .
H9B H 0.4247 0.8936 0.4419 0.063 Uiso 1 1 d R . .
H9C H 0.3422 1.0406 0.4130 0.063 Uiso 1 1 d R . .
C10 C 0.2933(4) 0.8583(5) 0.3146(3) 0.0300(11) Uani 1 1 d . . .
C11 C 0.2530(4) 0.9021(6) 0.2267(3) 0.0351(12) Uani 1 1 d . . .
H11 H 0.2692 1.0014 0.2087 0.042 Uiso 1 1 calc R . .
C12 C 0.1145(4) 0.7567(6) 0.0695(3) 0.0453(14) Uani 1 1 d . . .
H12A H 0.1254 0.6472 0.0515 0.068 Uiso 1 1 d R . .
H12B H 0.1321 0.8500 0.0466 0.068 Uiso 1 1 d R . .
H12C H 0.0429 0.7667 0.0473 0.068 Uiso 1 1 d R . .
C13 C 0.1827(4) 0.7666(6) 0.1702(3) 0.0319(12) Uani 1 1 d . . .
C14 C 0.0249(4) 0.1017(6) 0.1817(4) 0.0480(15) Uani 1 1 d . . .
H14A H -0.0420 0.1567 0.1476 0.072 Uiso 1 1 d R . .
H14B H 0.0182 -0.0149 0.1963 0.072 Uiso 1 1 d R . .
H14C H 0.0524 0.0984 0.1480 0.072 Uiso 1 1 d R . .
C15 C 0.0981(4) 0.2045(5) 0.2664(3) 0.0348(12) Uani 1 1 d . . .
C16 C 0.1234(4) 0.1699(6) 0.3518(4) 0.0388(13) Uani 1 1 d . . .
H16 H 0.0988 0.0765 0.3661 0.047 Uiso 1 1 calc R . .
C17 C 0.2341(4) 0.3097(6) 0.5081(4) 0.0476(15) Uani 1 1 d . . .
H17A H 0.1947 0.2341 0.5188 0.071 Uiso 1 1 d R . .
H17B H 0.2290 0.4272 0.5226 0.071 Uiso 1 1 d R . .
H17C H 0.3055 0.2739 0.5439 0.071 Uiso 1 1 d R . .
C18 C 0.1913(4) 0.2994(5) 0.4105(3) 0.0326(12) Uani 1 1 d . . .
C19 C 0.2069(3) 0.4195(5) 0.3589(3) 0.0267(11) Uani 1 1 d . . .
F1 F 0.1948(2) 0.3580(3) 0.16609(18) 0.0405(8) Uani 1 1 d . . .
F2 F 0.0305(2) 0.4540(3) 0.11482(17) 0.0366(7) Uani 1 1 d . . .
N1 N 0.5746(3) 0.5207(5) 0.6953(3) 0.0462(12) Uani 1 1 d . . .
H1B H 0.5954 0.4261 0.6813 0.055 Uiso 1 1 d R . .
H1C H 0.6120 0.5588 0.7514 0.055 Uiso 1 1 d R . .
N2 N 0.1459(3) 0.3560(4) 0.2696(3) 0.0308(10) Uani 1 1 d . . .
N3 N 0.1804(3) 0.6393(4) 0.2211(2) 0.0265(9) Uani 1 1 d . . .
O1 O 0.5140(3) 0.7953(5) 0.7444(2) 0.0548(11) Uani 1 1 d . . .
H1A H 0.4864 0.8707 0.7551 0.082 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'
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'
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'
O O 0.0106 0.0060 '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 108.3(4) . . ?
F2 B1 N2 111.6(4) . . ?
F1 B1 N2 110.4(4) . . ?
F2 B1 N3 111.0(4) . . ?
F1 B1 N3 108.4(4) . . ?
N2 B1 N3 107.1(4) . . ?
C6 C1 C2 120.5(4) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 119.9(5) . . ?
C3 C2 N1 118.1(5) . . ?
C1 C2 N1 121.8(5) . . ?
O1 C3 C4 124.0(5) . . ?
O1 C3 C2 115.5(5) . . ?
C4 C3 C2 120.5(5) . . ?
C3 C4 C5 119.2(5) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 121.7(5) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 118.2(4) . . ?
C5 C6 C7 121.1(4) . . ?
C1 C6 C7 120.6(4) . . ?
C19 C7 C8 121.7(4) . . ?
C19 C7 C6 118.9(4) . . ?
C8 C7 C6 119.4(4) . . ?
N3 C8 C10 108.0(4) . . ?
N3 C8 C7 119.2(4) . . ?
C10 C8 C7 132.8(4) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C8 106.9(4) . . ?
C11 C10 C9 123.1(4) . . ?
C8 C10 C9 129.9(4) . . ?
C10 C11 C13 108.1(4) . . ?
C10 C11 H11 126.0 . . ?
C13 C11 H11 126.0 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C13 C12 H12C 109.4 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C11 109.2(4) . . ?
N3 C13 C12 121.9(4) . . ?
C11 C13 C12 128.8(4) . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 109.5 . . ?
C15 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 C16 109.0(4) . . ?
N2 C15 C14 123.3(4) . . ?
C16 C15 C14 127.5(4) . . ?
C18 C16 C15 109.0(4) . . ?
C18 C16 H16 125.5 . . ?
C15 C16 H16 125.5 . . ?
C18 C17 H17A 109.4 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C18 C17 H17C 109.4 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 C19 106.3(5) . . ?
C16 C18 C17 124.7(4) . . ?
C19 C18 C17 129.0(4) . . ?
C7 C19 N2 119.9(4) . . ?
C7 C19 C18 132.5(4) . . ?
N2 C19 C18 107.2(4) . . ?
C2 N1 H1B 120.2 . . ?
C2 N1 H1C 119.8 . . ?
H1B N1 H1C 120.0 . . ?
C15 N2 C19 108.4(4) . . ?
C15 N2 B1 126.4(4) . . ?
C19 N2 B1 125.2(4) . . ?
C13 N3 C8 107.8(4) . . ?
C13 N3 B1 126.1(4) . . ?
C8 N3 B1 124.5(4) . . ?
C3 O1 H1A 109.4 . . ?
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 1.409(7) . ?
B1 F1 1.448(6) . ?
B1 N2 1.574(7) . ?
B1 N3 1.585(7) . ?
C1 C6 1.422(7) . ?
C1 C2 1.429(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.413(7) . ?
C2 N1 1.438(7) . ?
C3 O1 1.404(7) . ?
C3 C4 1.406(8) . ?
C4 C5 1.424(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.417(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.514(7) . ?
C7 C19 1.432(7) . ?
C7 C8 1.448(6) . ?
C8 N3 1.439(6) . ?
C8 C10 1.442(6) . ?
C9 C10 1.540(7) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.413(7) . ?
C11 C13 1.437(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.529(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N3 1.383(6) . ?
C14 C15 1.526(7) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N2 1.372(6) . ?
C15 C16 1.428(7) . ?
C16 C18 1.404(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.534(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.461(6) . ?
C19 N2 1.440(6) . ?
N1 H1B 0.8999 . ?
N1 H1C 0.9000 . ?
O1 H1A 0.8200 . ?
