#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/73/4107381.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_4107381
loop_
_publ_author_name
'Keitaro Umezawa'
'Yuki Nakamura'
'Hiroshi Makino'
'Daniel Citterio'
'Koji Suzuki'
_publ_contact_author_address
;
Department of Applied Chemistry
Faculty of Science and Technology
Keio University
3-14-1 Hiyoshi Kohoku-ku
Yokohama 223-8522
Japan
;
_publ_contact_author_email       ' Suzuki@applc.keio.ac.jp '
_publ_contact_author_fax         ' (81)45 566 1566 '
_publ_contact_author_name        ' Prof. Koji Suzuki '
_publ_contact_author_phone       ' (81)45 566 1568 '
_publ_section_title
;
 Bright, Color-Tunable Fluorescent Dyes in the Visible-Near-Infrared
 Region
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1550
_journal_page_last               1551
_journal_paper_doi               10.1021/ja077756j
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C28 H18 B F5 N2 O4 '
_chemical_formula_sum            'C28 H18 B F5 N2 O4'
_chemical_formula_weight         552.26
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             'Fri Aug  3 19:41:35 2007'
_audit_creation_method           'by teXsan'
_cell_angle_alpha                92.00(3)
_cell_angle_beta                 106.85(3)
_cell_angle_gamma                92.01(2)
_cell_formula_units_Z            2
_cell_length_a                   9.644(3)
_cell_length_b                   13.419(4)
_cell_length_c                   9.634(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298.2
_cell_measurement_theta_max      17.2
_cell_measurement_theta_min      15.4
_cell_volume                     1191.2(7)
_computing_cell_refinement       WinAFC
_computing_data_collection       WinAFC
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  SHELXL97
_computing_structure_solution    SHELXS97
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.189
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6612
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_description       block
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.18
_refine_diff_density_min         -1.08
_refine_ls_extinction_coef       0.0327
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.44
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     362
_refine_ls_number_reflns         2423
_refine_ls_R_factor_gt           0.129
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.436
_reflns_number_gt                2423
_reflns_number_total             5460
_reflns_threshold_expression     >2.0sigma(I)
_cod_data_source_file            ja077756j-file001.cif
_cod_data_source_block           ColorFL_K-4
_cod_original_cell_volume        1191.2(6)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C28 H18 B F5 N2 O4 '
_cod_database_code               4107381
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_calc_flag
F(1) F 0.0654(4) 0.2210(2) 0.2479(4) 0.079(1) Uani 1.00 d
F(2) F 0.2517(4) 0.2788(2) 0.4342(4) 0.076(1) Uani 1.00 d
F(3) F 0.6079(8) 0.2018(8) 0.0315(8) 0.210(4) Uani 1.00 d
F(4) F 0.554(2) 0.3280(6) -0.018(2) 0.38(1) Uani 1.00 d
F(5) F 0.4469(8) 0.228(1) -0.1194(7) 0.37(1) Uani 1.00 d
O(1) O 0.4130(4) -0.0771(3) 0.3161(4) 0.062(1) Uani 1.00 d
O(2) O 0.1841(4) 0.5769(3) 0.0872(4) 0.065(1) Uani 1.00 d
O(3) O 0.2616(5) -0.4404(3) 0.6581(5) 0.080(1) Uani 1.00 d
O(4) O -0.1588(5) 0.9388(3) 0.2376(5) 0.078(1) Uani 1.00 d
N(1) N 0.3018(5) 0.1636(3) 0.2601(5) 0.056(1) Uani 1.00 d
N(2) N 0.2392(5) 0.3353(3) 0.1981(5) 0.058(1) Uani 1.00 d
C(1) C 0.3221(6) -0.0771(4) 0.4054(6) 0.062(1) Uani 1.00 d
C(2) C 0.2568(6) 0.0112(4) 0.4081(6) 0.062(1) Uani 1.00 d
C(3) C 0.3099(6) 0.0730(4) 0.3165(6) 0.056(1) Uani 1.00 d
C(4) C 0.4028(6) 0.0162(4) 0.2612(6) 0.059(1) Uani 1.00 d
C(5) C 0.4591(6) 0.0696(4) 0.1730(6) 0.062(1) Uani 1.00 d
C(6) C 0.3937(6) 0.1645(4) 0.1689(6) 0.059(1) Uani 1.00 d
C(7) C 0.4051(6) 0.2493(4) 0.0960(6) 0.058(1) Uani 1.00 d
C(8) C 0.3305(6) 0.3356(4) 0.1051(6) 0.058(1) Uani 1.00 d
C(9) C 0.3265(7) 0.4310(4) 0.0408(6) 0.063(1) Uani 1.00 d
C(10) C 0.2376(6) 0.4831(4) 0.0958(6) 0.058(1) Uani 1.00 d
C(11) C 0.1841(6) 0.4272(4) 0.1893(6) 0.057(1) Uani 1.00 d
C(12) C 0.0918(6) 0.4889(4) 0.2426(6) 0.061(1) Uani 1.00 d
C(13) C 0.0958(6) 0.5769(4) 0.1792(6) 0.059(1) Uani 1.00 d
C(14) C 0.3115(6) -0.1714(4) 0.4721(6) 0.059(1) Uani 1.00 d
C(15) C 0.2147(6) -0.1846(4) 0.5548(6) 0.061(1) Uani 1.00 d
C(16) C 0.2006(7) -0.2729(4) 0.6132(7) 0.067(1) Uani 1.00 d
C(17) C 0.2836(6) -0.3539(4) 0.5965(6) 0.062(1) Uani 1.00 d
C(18) C 0.3812(7) -0.3401(4) 0.5156(7) 0.070(2) Uani 1.00 d
C(19) C 0.3946(7) -0.2501(4) 0.4558(7) 0.068(2) Uani 1.00 d
C(20) C 0.0281(6) 0.6713(4) 0.1893(6) 0.058(1) Uani 1.00 d
C(21) C 0.0456(7) 0.7488(4) 0.1080(7) 0.068(2) Uani 1.00 d
C(22) C -0.0154(8) 0.8412(4) 0.1194(7) 0.072(2) Uani 1.00 d
C(23) C -0.0943(7) 0.8527(4) 0.2161(7) 0.064(1) Uani 1.00 d
C(24) C -0.1147(7) 0.7750(4) 0.2997(7) 0.071(2) Uani 1.00 d
C(25) C -0.0534(7) 0.6847(4) 0.2862(6) 0.063(1) Uani 1.00 d
C(26) C 0.3475(7) -0.5214(4) 0.6437(7) 0.075(2) Uani 1.00 d
C(27) C -0.1420(8) 1.0201(4) 0.1509(8) 0.080(2) Uani 1.00 d
C(28) C 0.5023(7) 0.2498(4) -0.0001(6) 0.062(1) Uani 1.00 d
B(1) B 0.2091(7) 0.2496(4) 0.2890(7) 0.055(1) Uani 1.00 d
H(2) H 0.1893 0.0288 0.4594 0.0739 Uiso 1.00 calc
H(5) H 0.5276 0.0486 0.1247 0.0738 Uiso 1.00 calc
H(9) H 0.3783 0.4529 -0.0252 0.0770 Uiso 1.00 calc
H(12) H 0.0388 0.4712 0.3085 0.0752 Uiso 1.00 calc
H(15) H 0.1558 -0.1305 0.5680 0.0719 Uiso 1.00 calc
H(16) H 0.1326 -0.2811 0.6692 0.0798 Uiso 1.00 calc
H(18) H 0.4394 -0.3946 0.4998 0.0833 Uiso 1.00 calc
H(19) H 0.4627 -0.2408 0.4015 0.0817 Uiso 1.00 calc
H(21) H 0.1006 0.7396 0.0408 0.0828 Uiso 1.00 calc
H(22) H -0.0034 0.8942 0.0581 0.0843 Uiso 1.00 calc
H(24) H -0.1720 0.7845 0.3666 0.0839 Uiso 1.00 calc
H(25) H -0.0670 0.6308 0.3448 0.0752 Uiso 1.00 calc
H(26A) H 0.3237 -0.5784 0.6907 0.0901 Uiso 1.00 calc
H(26B) H 0.3318 -0.5407 0.5427 0.0901 Uiso 1.00 calc
H(26C) H 0.4487 -0.5041 0.6849 0.0901 Uiso 1.00 calc
H(27A) H -0.0410 1.0396 0.1694 0.0971 Uiso 1.00 calc
H(27B) H -0.1803 1.0016 0.0496 0.0971 Uiso 1.00 calc
H(27C) H -0.1909 1.0767 0.1718 0.0971 Uiso 1.00 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C)
;
B B 0.001 0.001
;International Tables for Crystallography
(1992, Vol. C)
;
F F 0.017 0.010
;International Tables for Crystallography
(1992, Vol. C)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C)
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 B1 1.363(1)
F2 B1 1.377(1)
F3 C28 1.193(10)
F4 C28 1.185(13)
F5 C28 1.141(9)
O1 C1 1.395(8)
O1 C4 1.372(6)
O2 C10 1.374(6)
O2 C13 1.395(8)
O3 C17 1.360(7)
O3 C26 1.417(8)
O4 C23 1.370(7)
O4 C27 1.429(8)
N1 C3 1.345(7)
N1 C6 1.417(8)
N1 B1 1.550(8)
N2 C8 1.427(8)
N2 C11 1.356(6)
N2 B1 1.538(8)
C1 C2 1.365(8)
C1 C14 1.452(8)
C2 C3 1.418(9)
C2 H2 0.96
C3 C4 1.401(9)
C4 C5 1.347(9)
C5 C6 1.438(8)
C5 H5 0.96
C6 C7 1.376(8)
C7 C8 1.398(8)
C7 C28 1.496(10)
C8 C9 1.438(8)
C9 C10 1.336(9)
C9 H9 0.96
C10 C11 1.390(8)
C11 C12 1.425(9)
C12 C13 1.353(8)
C12 H12 0.96
C13 C20 1.458(8)
C14 C15 1.403(9)
C14 C19 1.379(8)
C15 C16 1.349(8)
C15 H15 0.96
C16 C17 1.404(8)
C16 H16 0.97
C17 C18 1.396(10)
C18 H18 0.97
C19 C18 1.375(9)
C19 H19 0.96
C20 C21 1.359(8)
C20 C25 1.394(9)
C21 C22 1.405(9)
C21 H21 0.96
C22 C23 1.371(11)
C22 H22 0.97
C23 C24 1.381(9)
C24 C25 1.386(8)
C24 H24 0.97
C25 H25 0.96
C26 H26A 0.96
C26 H26B 0.96
C26 H26C 0.96
C27 H27A 0.96
C27 H27B 0.96
C27 H27C 0.95
