#------------------------------------------------------------------------------
#$Date: 2016-03-25 15:56:59 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179944 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/39/7023995.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_7023995
loop_
_publ_author_name
'Luo, Geng-Geng'
'Xia, Jiu-Xu'
'Fang, Kai'
'Zhao, Qing-Hua'
'Wu, Ji-Huai'
'Dai, Jing-Cao'
_publ_section_title
;
 Discovery of polymorphism-dependent emission for crystalline
 boron-dipyrromethene dye.
;
_journal_issue                   46
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              16268
_journal_page_last               16271
_journal_paper_doi               10.1039/c3dt52325j
_journal_volume                  42
_journal_year                    2013
_chemical_formula_sum            'C21 H21 B F2 N2 O2'
_chemical_formula_weight         382.21
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3318(13)
_cell_length_b                   12.0855(17)
_cell_length_c                   18.610(2)
_cell_measurement_temperature    173(2)
_cell_volume                     1873.9(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'SuperNova (Cu) X-ray source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6851
_diffrn_reflns_theta_full        65.78
_diffrn_reflns_theta_max         65.78
_diffrn_reflns_theta_min         4.36
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_max  0.9365
_exptl_absorpt_correction_T_min  0.8192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro, Agilent Technologies
Version 1.171.35.21 
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0504
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1479
_reflns_number_gt                2740
_reflns_number_total             3129
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3dt52325j.txt
_cod_data_source_block           939166
_cod_original_cell_volume        1874.0(5)
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7023995
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
B1 B 0.6008(4) 0.8335(3) 0.62809(19) 0.0269(8) Uani 1 1 d .
N1 N 0.5384(3) 0.8899(2) 0.55820(13) 0.0273(6) Uani 1 1 d .
N2 N 0.7736(3) 0.8762(2) 0.63977(12) 0.0265(6) Uani 1 1 d .
O1 O 1.2640(3) 1.2254(2) 0.30749(13) 0.0390(6) Uani 1 1 d .
O2 O 1.0665(3) 1.35232(17) 0.30996(11) 0.0314(5) Uani 1 1 d .
F1 F 0.5032(2) 0.85960(16) 0.68624(9) 0.0357(5) Uani 1 1 d .
F2 F 0.6025(2) 0.71904(14) 0.61880(9) 0.0334(5) Uani 1 1 d .
C1 C 1.1376(4) 1.2584(2) 0.33101(16) 0.0265(7) Uani 1 1 d .
C2 C 1.1473(5) 1.4100(3) 0.25217(16) 0.0362(8) Uani 1 1 d .
H2A H 1.0876 1.4774 0.2402 0.054 Uiso 1 1 calc R
H2B H 1.1527 1.3619 0.2098 0.054 Uiso 1 1 calc R
H2C H 1.2562 1.4297 0.2674 0.054 Uiso 1 1 calc R
C3 C 1.0426(4) 1.1978(2) 0.38614(16) 0.0258(7) Uani 1 1 d .
C4 C 0.9393(4) 1.2498(2) 0.43475(16) 0.0270(7) Uani 1 1 d .
H4A H 0.9269 1.3279 0.4335 0.032 Uiso 1 1 calc R
C5 C 0.8549(4) 1.1879(3) 0.48482(17) 0.0282(7) Uani 1 1 d .
H5A H 0.7857 1.2240 0.5179 0.034 Uiso 1 1 calc R
C6 C 0.8709(4) 1.0728(2) 0.48702(16) 0.0240(6) Uani 1 1 d .
C7 C 0.9752(4) 1.0210(3) 0.43814(16) 0.0289(7) Uani 1 1 d .
H7A H 0.9868 0.9428 0.4390 0.035 Uiso 1 1 calc R
C8 C 1.0611(4) 1.0829(2) 0.38880(16) 0.0284(7) Uani 1 1 d .
H8A H 1.1330 1.0473 0.3566 0.034 Uiso 1 1 calc R
C9 C 0.7765(4) 1.0005(2) 0.53657(15) 0.0253(7) Uani 1 1 d .
C10 C 0.8503(4) 0.9591(3) 0.59885(15) 0.0258(6) Uani 1 1 d .
C11 C 1.0039(4) 0.9792(2) 0.63018(16) 0.0280(7) Uani 1 1 d .
C12 C 1.0160(4) 0.9077(3) 0.68769(16) 0.0311(7) Uani 1 1 d .
H12A H 1.1057 0.9016 0.7190 0.037 Uiso 1 1 calc R
C13 C 0.8749(4) 0.8458(2) 0.69234(16) 0.0282(7) Uani 1 1 d .
C14 C 0.4006(4) 0.8635(3) 0.52360(17) 0.0287(7) Uani 1 1 d .
C15 C 0.3945(4) 0.9214(3) 0.45873(17) 0.0311(7) Uani 1 1 d .
H15A H 0.3100 0.9176 0.4245 0.037 Uiso 1 1 calc R
C16 C 0.5309(4) 0.9850(2) 0.45240(16) 0.0292(7) Uani 1 1 d .
C17 C 0.6238(4) 0.9653(2) 0.51615(16) 0.0266(6) Uani 1 1 d .
C18 C 1.1310(4) 1.0595(3) 0.60673(16) 0.0298(7) Uani 1 1 d .
H18A H 1.2234 1.0542 0.6391 0.045 Uiso 1 1 calc R
H18B H 1.0877 1.1349 0.6081 0.045 Uiso 1 1 calc R
H18C H 1.1648 1.0418 0.5576 0.045 Uiso 1 1 calc R
C19 C 0.8363(5) 0.7562(3) 0.74559(17) 0.0371(8) Uani 1 1 d .
H19A H 0.7285 0.7273 0.7360 0.056 Uiso 1 1 calc R
H19B H 0.8403 0.7866 0.7944 0.056 Uiso 1 1 calc R
H19C H 0.9149 0.6963 0.7411 0.056 Uiso 1 1 calc R
C20 C 0.2794(4) 0.7847(3) 0.55323(19) 0.0342(7) Uani 1 1 d .
H20A H 0.3164 0.7568 0.5998 0.051 Uiso 1 1 calc R
H20B H 0.2657 0.7226 0.5199 0.051 Uiso 1 1 calc R
H20C H 0.1766 0.8229 0.5594 0.051 Uiso 1 1 calc R
C21 C 0.5674(5) 1.0601(3) 0.39002(18) 0.0387(8) Uani 1 1 d .
H21A H 0.4804 1.0555 0.3547 0.058 Uiso 1 1 calc R
H21B H 0.6685 1.0373 0.3675 0.058 Uiso 1 1 calc R
H21C H 0.5771 1.1365 0.4072 0.058 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 '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
F1 B1 F2 109.1(3)
F1 B1 N2 111.1(3)
F2 B1 N2 109.9(3)
F1 B1 N1 110.8(3)
F2 B1 N1 109.5(3)
N2 B1 N1 106.4(2)
C14 N1 C17 108.6(3)
C14 N1 B1 125.2(3)
C17 N1 B1 125.7(3)
C13 N2 C10 107.6(3)
C13 N2 B1 126.6(3)
C10 N2 B1 125.7(2)
C1 O2 C2 114.8(3)
O1 C1 O2 124.0(3)
O1 C1 C3 123.5(3)
O2 C1 C3 112.5(3)
C4 C3 C8 119.4(3)
C4 C3 C1 123.6(3)
C8 C3 C1 117.0(3)
C5 C4 C3 120.3(3)
C4 C5 C6 120.6(3)
C5 C6 C7 118.9(3)
C5 C6 C9 123.4(3)
C7 C6 C9 117.7(3)
C8 C7 C6 120.6(3)
C7 C8 C3 120.2(3)
C17 C9 C10 121.0(3)
C17 C9 C6 119.4(3)
C10 C9 C6 119.2(3)
C9 C10 N2 120.0(3)
C9 C10 C11 132.0(3)
N2 C10 C11 107.9(2)
C12 C11 C10 106.0(3)
C12 C11 C18 125.4(3)
C10 C11 C18 128.6(3)
C11 C12 C13 108.8(3)
N2 C13 C12 109.7(3)
N2 C13 C19 122.9(3)
C12 C13 C19 127.4(3)
N1 C14 C15 108.9(3)
N1 C14 C20 123.2(3)
C15 C14 C20 127.9(3)
C16 C15 C14 108.9(3)
C15 C16 C17 106.4(3)
C15 C16 C21 124.7(3)
C17 C16 C21 128.9(3)
C9 C17 N1 120.8(3)
C9 C17 C16 131.8(3)
N1 C17 C16 107.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
B1 F1 1.390(4)
B1 F2 1.394(4)
B1 N2 1.545(4)
B1 N1 1.558(4)
N1 C14 1.354(4)
N1 C17 1.396(4)
N2 C13 1.344(4)
N2 C10 1.411(4)
O1 C1 1.208(4)
O2 C1 1.339(4)
O2 C2 1.448(4)
C1 C3 1.488(4)
C3 C4 1.398(4)
C3 C8 1.398(4)
C4 C5 1.387(5)
C5 C6 1.397(4)
C6 C7 1.405(4)
C6 C9 1.495(4)
C7 C8 1.384(4)
C9 C17 1.394(5)
C9 C10 1.404(4)
C10 C11 1.427(4)
C11 C12 1.379(4)
C11 C18 1.501(4)
C12 C13 1.397(5)
C13 C19 1.502(4)
C14 C15 1.397(5)
C14 C20 1.494(5)
C15 C16 1.377(5)
C16 C17 1.436(4)
C16 C21 1.505(4)
