#------------------------------------------------------------------------------
#$Date: 2016-03-25 15:47:38 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179936 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/31/7023141.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_7023141
loop_
_publ_author_name
'Maeda, Hiromitsu'
'Nishimura, Yuki'
'Hiroto, Satoru'
'Shinokubo, Hiroshi'
_publ_section_title
;
 Assembled structures of dipyrrins and their oligomers bridged by
 dioxy-boron moieties.
;
_journal_issue                   45
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              15885
_journal_page_last               15888
_journal_paper_doi               10.1039/c3dt50783a
_journal_volume                  42
_journal_year                    2013
_chemical_formula_moiety         'C32 H32 B2 F4 N4, 2(C H Cl3) '
_chemical_formula_sum            'C34 H34 B2 Cl6 F4 N4'
_chemical_formula_weight         808.97
_chemical_name_systematic
;
?
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                70.3780(18)
_cell_angle_beta                 73.462(2)
_cell_angle_gamma                86.088(2)
_cell_formula_units_Z            1
_cell_length_a                   6.9862(2)
_cell_length_b                   11.3882(3)
_cell_length_c                   12.5660(4)
_cell_measurement_temperature    93(2)
_cell_volume                     902.33(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_sigmaI/netI    0.0883
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9206
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_diffrn_reflns_theta_min         3.89
_exptl_absorpt_coefficient_mu    4.797
_exptl_absorpt_correction_T_max  0.6455
_exptl_absorpt_correction_T_min  0.4471
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0546
_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)+(0.0610P)²+0.1753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1539
_reflns_number_gt                2207
_reflns_number_total             3206
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3dt50783a.txt
_cod_data_source_block           01109ma
_cod_original_cell_volume        902.32(5)
_cod_database_code               7023141
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.03082(16) 0.64841(9) 0.42368(8) 0.0429(3) Uani 1 1 d .
Cl2 Cl 0.22060(16) 0.88460(9) 0.37869(10) 0.0433(3) Uani 1 1 d .
Cl3 Cl 0.05389(18) 0.84786(10) 0.20605(9) 0.0477(3) Uani 1 1 d .
C17 C 0.1736(6) 0.7764(3) 0.3156(3) 0.0309(9) Uani 1 1 d .
H17 H 0.3046 0.7458 0.2785 0.037 Uiso 1 1 calc R
F1 F 0.4388(3) 0.61367(18) 0.20077(17) 0.0321(5) Uani 1 1 d .
F2 F 0.7515(3) 0.62161(18) 0.21784(18) 0.0363(6) Uani 1 1 d .
N1 N 0.6416(4) 0.4344(2) 0.1982(2) 0.0194(6) Uani 1 1 d .
N2 N 0.7158(4) 0.6327(3) 0.0294(2) 0.0236(7) Uani 1 1 d .
C1 C 0.3655(5) 0.0948(3) 0.4883(3) 0.0222(7) Uani 1 1 d .
H13 H 0.2716 0.1594 0.4810 0.027 Uiso 1 1 calc R
C2 C 0.7369(5) 0.7547(3) -0.0365(3) 0.0259(8) Uani 1 1 d .
C3 C 0.5263(5) 0.3889(3) 0.4149(3) 0.0264(8) Uani 1 1 d .
H1 H 0.6339 0.4402 0.4144 0.040 Uiso 1 1 calc R
H2 H 0.5010 0.3144 0.4854 0.040 Uiso 1 1 calc R
H3 H 0.4047 0.4371 0.4154 0.040 Uiso 1 1 calc R
C4 C 0.5866(5) 0.3504(3) 0.3077(3) 0.0196(7) Uani 1 1 d .
C5 C 0.7622(5) 0.4337(3) -0.0020(3) 0.0227(8) Uani 1 1 d .
H14 H 0.8010 0.3881 -0.0553 0.027 Uiso 1 1 calc R
C6 C 0.8328(5) 0.6470(3) -0.1632(3) 0.0256(8) Uani 1 1 d .
C7 C 0.7145(5) 0.1388(3) 0.1283(3) 0.0250(8) Uani 1 1 d .
H4 H 0.8464 0.1055 0.1321 0.037 Uiso 1 1 calc R
H5 H 0.7119 0.1724 0.0459 0.037 Uiso 1 1 calc R
H6 H 0.6123 0.0719 0.1718 0.037 Uiso 1 1 calc R
C8 C 0.6972(5) 0.3690(3) 0.1182(3) 0.0201(7) Uani 1 1 d .
C9 C 0.5489(5) 0.1115(3) 0.4021(3) 0.0202(7) Uani 1 1 d .
C10 C 0.9060(5) 0.6131(3) -0.2726(3) 0.0289(8) Uani 1 1 d .
H7 H 0.7919 0.6010 -0.2990 0.043 Uiso 1 1 calc R
H8 H 0.9798 0.5358 -0.2564 0.043 Uiso 1 1 calc R
H9 H 0.9943 0.6803 -0.3342 0.043 Uiso 1 1 calc R
C11 C 0.6730(5) 0.2402(3) 0.1816(3) 0.0201(7) Uani 1 1 d .
C16 C 0.3180(5) -0.0133(3) 0.5837(3) 0.0233(8) Uani 1 1 d .
H15 H 0.1925 -0.0214 0.6410 0.028 Uiso 1 1 calc R
C12 C 0.6884(6) 0.8559(3) 0.0171(3) 0.0333(9) Uani 1 1 d .
H10 H 0.5518 0.8424 0.0692 0.050 Uiso 1 1 calc R
H11 H 0.6996 0.9369 -0.0453 0.050 Uiso 1 1 calc R
H12 H 0.7821 0.8548 0.0624 0.050 Uiso 1 1 calc R
C13 C 0.6011(5) 0.2284(3) 0.3007(3) 0.0209(7) Uani 1 1 d .
B1 B 0.6358(6) 0.5779(4) 0.1651(4) 0.0249(9) Uani 1 1 d .
C14 C 0.7718(5) 0.5631(3) -0.0461(3) 0.0217(7) Uani 1 1 d .
C15 C 0.8095(5) 0.7658(3) -0.1554(3) 0.0268(8) Uani 1 1 d .
H16 H 0.8380 0.8417 -0.2197 0.032 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'
B B 0.0090 0.0039 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
Cl1 C17 Cl3 110.6(2) . .
Cl1 C17 Cl2 110.6(2) . .
Cl3 C17 Cl2 110.58(19) . .
Cl1 C17 H17 108.3 . .
Cl3 C17 H17 108.3 . .
Cl2 C17 H17 108.3 . .
C4 N1 C8 108.0(3) . .
C4 N1 B1 126.6(3) . .
C8 N1 B1 125.3(3) . .
C2 N2 C14 108.1(3) . .
C2 N2 B1 126.7(3) . .
C14 N2 B1 125.2(3) . .
C16 C1 C9 121.4(3) . .
C16 C1 H13 119.3 . .
C9 C1 H13 119.3 . .
N2 C2 C15 109.3(3) . .
N2 C2 C12 122.2(3) . .
C15 C2 C12 128.6(3) . .
C4 C3 H1 109.5 . .
C4 C3 H2 109.5 . .
H1 C3 H2 109.5 . .
C4 C3 H3 109.5 . .
H1 C3 H3 109.5 . .
H2 C3 H3 109.5 . .
N1 C4 C13 109.4(3) . .
N1 C4 C3 122.0(3) . .
C13 C4 C3 128.5(3) . .
C14 C5 C8 121.8(3) . .
C14 C5 H14 119.1 . .
C8 C5 H14 119.1 . .
C15 C6 C14 106.3(3) . .
C15 C6 C10 127.1(3) . .
C14 C6 C10 126.6(3) . .
C11 C7 H4 109.5 . .
C11 C7 H5 109.5 . .
H4 C7 H5 109.5 . .
C11 C7 H6 109.5 . .
H4 C7 H6 109.5 . .
H5 C7 H6 109.5 . .
C5 C8 N1 120.0(3) . .
C5 C8 C11 131.4(3) . .
N1 C8 C11 108.6(3) . .
C1 C9 C16 117.2(3) . 2_656
C1 C9 C13 121.4(3) . .
C16 C9 C13 121.4(3) 2_656 .
C6 C10 H7 109.5 . .
C6 C10 H8 109.5 . .
H7 C10 H8 109.5 . .
C6 C10 H9 109.5 . .
H7 C10 H9 109.5 . .
H8 C10 H9 109.5 . .
C13 C11 C8 106.7(3) . .
C13 C11 C7 128.0(3) . .
C8 C11 C7 125.2(3) . .
C1 C16 C9 121.4(3) . 2_656
C1 C16 H15 119.3 . .
C9 C16 H15 119.3 2_656 .
C2 C12 H10 109.5 . .
C2 C12 H11 109.5 . .
H10 C12 H11 109.5 . .
C2 C12 H12 109.5 . .
H10 C12 H12 109.5 . .
H11 C12 H12 109.5 . .
C11 C13 C4 107.2(3) . .
C11 C13 C9 127.3(3) . .
C4 C13 C9 125.5(3) . .
F2 B1 F1 108.9(3) . .
F2 B1 N1 111.5(3) . .
F1 B1 N1 109.7(3) . .
F2 B1 N2 110.4(3) . .
F1 B1 N2 109.5(3) . .
N1 B1 N2 107.0(3) . .
C5 C14 N2 120.6(3) . .
C5 C14 C6 131.2(3) . .
N2 C14 C6 108.2(3) . .
C6 C15 C2 108.2(3) . .
C6 C15 H16 125.9 . .
C2 C15 H16 125.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C17 1.750(4) .
Cl2 C17 1.764(4) .
Cl3 C17 1.751(4) .
C17 H17 1.0000 .
F1 B1 1.399(5) .
F2 B1 1.387(4) .
N1 C4 1.349(4) .
N1 C8 1.400(4) .
N1 B1 1.545(5) .
N2 C2 1.350(4) .
N2 C14 1.390(4) .
N2 B1 1.549(5) .
C1 C16 1.379(5) .
C1 C9 1.399(4) .
C1 H13 0.9500 .
C2 C15 1.399(5) .
C2 C12 1.495(5) .
C3 C4 1.495(4) .
C3 H1 0.9800 .
C3 H2 0.9800 .
C3 H3 0.9800 .
C4 C13 1.417(4) .
C5 C14 1.389(5) .
C5 C8 1.392(5) .
C5 H14 0.9500 .
C6 C15 1.385(5) .
C6 C14 1.419(5) .
C6 C10 1.493(5) .
C7 C11 1.493(4) .
C7 H4 0.9800 .
C7 H5 0.9800 .
C7 H6 0.9800 .
C8 C11 1.410(5) .
C9 C16 1.402(4) 2_656
C9 C13 1.480(4) .
C10 H7 0.9800 .
C10 H8 0.9800 .
C10 H9 0.9800 .
C11 C13 1.399(4) .
C16 C9 1.402(4) 2_656
C16 H15 0.9500 .
C12 H10 0.9800 .
C12 H11 0.9800 .
C12 H12 0.9800 .
C15 H16 0.9500 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C14 N2 C2 C15 -0.8(4) . .
B1 N2 C2 C15 -178.7(3) . .
C14 N2 C2 C12 179.8(3) . .
B1 N2 C2 C12 1.9(5) . .
C8 N1 C4 C13 -1.3(4) . .
B1 N1 C4 C13 176.0(3) . .
C8 N1 C4 C3 177.4(3) . .
B1 N1 C4 C3 -5.2(5) . .
C14 C5 C8 N1 -0.7(5) . .
C14 C5 C8 C11 179.0(3) . .
C4 N1 C8 C5 -179.6(3) . .
B1 N1 C8 C5 3.0(5) . .
C4 N1 C8 C11 0.6(4) . .
B1 N1 C8 C11 -176.8(3) . .
C16 C1 C9 C16 0.5(5) . 2_656
C16 C1 C9 C13 -179.1(3) . .
C5 C8 C11 C13 -179.4(3) . .
N1 C8 C11 C13 0.4(4) . .
C5 C8 C11 C7 -0.4(6) . .
N1 C8 C11 C7 179.4(3) . .
C9 C1 C16 C9 -0.5(5) . 2_656
C8 C11 C13 C4 -1.1(4) . .
C7 C11 C13 C4 179.9(3) . .
C8 C11 C13 C9 178.9(3) . .
C7 C11 C13 C9 0.0(6) . .
N1 C4 C13 C11 1.6(4) . .
C3 C4 C13 C11 -177.1(3) . .
N1 C4 C13 C9 -178.5(3) . .
C3 C4 C13 C9 2.9(6) . .
C1 C9 C13 C11 -129.5(4) . .
C16 C9 C13 C11 51.0(5) 2_656 .
C1 C9 C13 C4 50.5(5) . .
C16 C9 C13 C4 -129.0(4) 2_656 .
C4 N1 B1 F2 58.6(5) . .
C8 N1 B1 F2 -124.4(3) . .
C4 N1 B1 F1 -62.0(4) . .
C8 N1 B1 F1 114.9(3) . .
C4 N1 B1 N2 179.3(3) . .
C8 N1 B1 N2 -3.7(4) . .
C2 N2 B1 F2 -58.3(5) . .
C14 N2 B1 F2 124.2(3) . .
C2 N2 B1 F1 61.5(4) . .
C14 N2 B1 F1 -116.0(3) . .
C2 N2 B1 N1 -179.7(3) . .
C14 N2 B1 N1 2.8(4) . .
C8 C5 C14 N2 -0.2(5) . .
C8 C5 C14 C6 179.9(3) . .
C2 N2 C14 C5 -179.1(3) . .
B1 N2 C14 C5 -1.1(5) . .
C2 N2 C14 C6 0.9(4) . .
B1 N2 C14 C6 178.8(3) . .
C15 C6 C14 C5 179.3(3) . .
C10 C6 C14 C5 -0.4(6) . .
C15 C6 C14 N2 -0.7(4) . .
C10 C6 C14 N2 179.6(3) . .
C14 C6 C15 C2 0.2(4) . .
C10 C6 C15 C2 179.9(3) . .
N2 C2 C15 C6 0.4(4) . .
C12 C2 C15 C6 179.8(4) . .
