# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               'To Be Published'
_journal_coden_cambridge         0353
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
_publ_author_address
'Naoya Sakamoto'
;
Graduate School of Pure and Applied Sciences,
University of Tsukuba,
1-1-1 Tennodai Tsukuba, Ibaraki, 305-8571, Japan
;
'Chusaku Ikeda'
;
Graduate School of Pure and Applied Sciences,
University of Tsukuba,
1-1-1 Tennodai Tsukuba, Ibaraki, 305-8571, Japan
;
'Masaki Yamamura'
;
Graduate School of Pure and Applied Sciences,
University of Tsukuba,
1-1-1 Tennodai Tsukuba, Ibaraki, 305-8571, Japan
;
'Tatsuya Nabeshima'
;
Graduate School of Pure and Applied Sciences,
University of Tsukuba,
1-1-1 Tennodai Tsukuba, Ibaraki, 305-8571, Japan
;
_publ_contact_author_address     
;
Graduate School of Pure and Applied Sciences,
University of Tsukuba,
1-1-1 Tennodai Tsukuba, Ibaraki, 305-8571, Japan
;
_publ_contact_author_email       nabesima@chem.tsukuba.ac.jp
_publ_contact_author_fax         +81-29-853-4507
_publ_contact_author_phone       +81-29-853-4507

_publ_contact_author_name        'Tatsuya Nabeshima'
_publ_requested_category         FO
_publ_section_title              
;
alpha-Bridged BODIPY Oligomers with Switchable Near-IR Photoproperties by External-Stimuli-Induced Foldamer Formation and Disruption
;

data_dimerbf2_0ma
_database_code_depnum_ccdc_archive 'CCDC 841547'
#TrackingRef '6876_web_deposit_cif_file_0_NaoyaSakamoto_1314191232.BODIPYdimer.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C58 H52 B2 F4 N4 O4, 2(C H2 Cl2)'
_chemical_formula_sum            'C60 H56 B2 Cl4 F4 N4 O4'
_chemical_formula_weight         1136.51

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   15.0748(14)
_cell_length_b                   9.8130(9)
_cell_length_c                   20.2660(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.9900(10)
_cell_angle_gamma                90.00
_cell_volume                     2799.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      1.45
_cell_measurement_theta_max      27.55

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1180
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8976
_exptl_absorpt_correction_T_max  0.9217
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31126
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0138
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         27.55
_reflns_number_total             6427
_reflns_number_gt                5920
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 '
_computing_cell_refinement       'APEX2 '
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0554P)^2^+3.9087P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6427
_refine_ls_number_parameters     357
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1405
_refine_ls_wR_factor_gt          0.1377
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
O2 O 0.60549(9) 0.26746(13) 0.50314(7) 0.0237(3) Uani 1 1 d . . .
C11 C 0.06672(11) 0.27991(17) 0.39393(9) 0.0160(3) Uani 1 1 d . . .
C8 C -0.02690(11) 0.43752(17) 0.29931(9) 0.0155(3) Uani 1 1 d . . .
C12 C -0.00451(12) 0.18103(18) 0.38574(9) 0.0176(3) Uani 1 1 d . . .
H1 H -0.0666 0.1807 0.3508 0.021 Uiso 1 1 calc R . .
C10 C 0.06601(11) 0.39293(17) 0.35236(8) 0.0152(3) Uani 1 1 d . . .
C20 C 0.45509(12) 0.39005(18) 0.45848(9) 0.0194(3) Uani 1 1 d . . .
H2 H 0.4244 0.3150 0.4298 0.023 Uiso 1 1 calc R . .
C2 C -0.09321(12) 0.50061(17) 0.32360(9) 0.0174(3) Uani 1 1 d . . .
C7 C -0.04882(12) 0.41233(17) 0.22698(9) 0.0177(3) Uani 1 1 d . . .
C13 C 0.03286(12) 0.08557(18) 0.43784(9) 0.0184(3) Uani 1 1 d . . .
H3 H 0.0021 0.0050 0.4444 0.022 Uiso 1 1 calc R . .
C16 C 0.16544(12) 0.58133(18) 0.32728(9) 0.0188(3) Uani 1 1 d . . .
H4 H 0.1194 0.6286 0.2895 0.023 Uiso 1 1 calc R . .
C15 C 0.14966(11) 0.46423(17) 0.36195(9) 0.0163(3) Uani 1 1 d . . .
C14 C 0.12556(12) 0.12863(17) 0.48005(9) 0.0163(3) Uani 1 1 d . . .
C26 C 0.22351(13) 0.1478(2) 0.60859(10) 0.0234(4) Uani 1 1 d . . .
H5 H 0.2144 0.2437 0.6051 0.028 Uiso 1 1 calc R . .
C22 C 0.55097(12) 0.38017(18) 0.50034(9) 0.0193(3) Uani 1 1 d . . .
C25 C 0.18597(12) 0.06795(18) 0.54791(9) 0.0175(3) Uani 1 1 d . . .
C17 C 0.26043(12) 0.61425(18) 0.35862(9) 0.0207(3) Uani 1 1 d . . .
H6 H 0.2918 0.6889 0.3466 0.025 Uiso 1 1 calc R . .
C30 C 0.20001(12) -0.07402(18) 0.55425(9) 0.0191(3) Uani 1 1 d . . .
C6 C -0.13802(12) 0.45026(19) 0.17965(9) 0.0206(3) Uani 1 1 d . . .
H7 H -0.1532 0.4340 0.1306 0.025 Uiso 1 1 calc R . .
C3 C -0.18187(12) 0.53581(19) 0.27424(10) 0.0209(4) Uani 1 1 d . . .
H8 H -0.2274 0.5776 0.2902 0.025 Uiso 1 1 calc R . .
C19 C 0.40320(12) 0.50821(18) 0.45792(9) 0.0182(3) Uani 1 1 d . . .
C18 C 0.30227(12) 0.51688(17) 0.41174(9) 0.0177(3) Uani 1 1 d . . .
C1 C -0.06999(13) 0.5380(2) 0.40027(9) 0.0225(4) Uani 1 1 d . . .
H12 H -0.0421 0.6294 0.4090 0.034 Uiso 1 1 calc R . .
H13 H -0.0246 0.4720 0.4304 0.034 Uiso 1 1 calc R . .
H14 H -0.1283 0.5367 0.4112 0.034 Uiso 1 1 calc R . .
C9 C 0.02106(13) 0.3416(2) 0.20060(10) 0.0230(4) Uani 1 1 d . . .
H15 H -0.0111 0.3146 0.1512 0.035 Uiso 1 1 calc R . .
H16 H 0.0462 0.2604 0.2294 0.035 Uiso 1 1 calc R . .
H17 H 0.0734 0.4039 0.2041 0.035 Uiso 1 1 calc R . .
C28 C 0.28740(14) -0.0493(2) 0.67910(10) 0.0283(4) Uani 1 1 d . . .
H9 H 0.3220 -0.0891 0.7237 0.034 Uiso 1 1 calc R . .
C29 C 0.25101(13) -0.1318(2) 0.61991(10) 0.0241(4) Uani 1 1 d . . .
H10 H 0.2608 -0.2275 0.6240 0.029 Uiso 1 1 calc R . .
C24 C 0.56023(14) 0.1530(2) 0.46112(12) 0.0291(4) Uani 1 1 d . . .
H18 H 0.5064 0.1241 0.4740 0.044 Uiso 1 1 calc R . .
H19 H 0.6058 0.0779 0.4694 0.044 Uiso 1 1 calc R . .
H20 H 0.5374 0.1784 0.4110 0.044 Uiso 1 1 calc R . .
C4 C -0.20539(12) 0.51140(19) 0.20237(10) 0.0222(4) Uani 1 1 d . . .
C27 C 0.27389(15) 0.0903(2) 0.67392(10) 0.0295(4) Uani 1 1 d . . .
H11 H 0.2988 0.1463 0.7147 0.035 Uiso 1 1 calc R . .
C5 C -0.30150(14) 0.5512(3) 0.14999(11) 0.0341(5) Uani 1 1 d . . .
H21 H -0.2945 0.6294 0.1222 0.051 Uiso 1 1 calc R . .
H22 H -0.3436 0.5759 0.1754 0.051 Uiso 1 1 calc R . .
H23 H -0.3288 0.4743 0.1184 0.051 Uiso 1 1 calc R . .
N2 N 0.23573(10) 0.42480(15) 0.41351(7) 0.0162(3) Uani 1 1 d . . .
N1 N 0.14639(10) 0.24497(14) 0.45251(7) 0.0156(3) Uani 1 1 d . . .
B1 B 0.24090(13) 0.32797(19) 0.47617(10) 0.0160(3) Uani 1 1 d . . .
F1 F 0.31658(7) 0.23863(10) 0.49299(5) 0.0187(2) Uani 1 1 d . . .
F2 F 0.24905(7) 0.41026(11) 0.53429(5) 0.0207(2) Uani 1 1 d . . .
O1 O 0.16215(10) -0.14676(13) 0.49347(7) 0.0241(3) Uani 1 1 d . . .
C31 C 0.17157(15) -0.29177(19) 0.49916(11) 0.0271(4) Uani 1 1 d . . .
H24 H 0.2391 -0.3162 0.5174 0.041 Uiso 1 1 calc R . .
H25 H 0.1407 -0.3330 0.4525 0.041 Uiso 1 1 calc R . .
H26 H 0.1414 -0.3255 0.5315 0.041 Uiso 1 1 calc R . .
Cl1 Cl 0.46739(5) 0.79674(9) 0.33128(6) 0.0725(3) Uani 1 1 d . . .
Cl2 Cl 0.54927(7) 0.5596(2) 0.28913(7) 0.1472(8) Uani 1 1 d . . .
C32 C 0.54810(17) 0.6622(3) 0.35745(12) 0.0414(6) Uani 1 1 d . . .
H27 H 0.6126 0.6999 0.3813 0.050 Uiso 1 1 calc R . .
H28 H 0.5325 0.6058 0.3923 0.050 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0150(6) 0.0182(6) 0.0348(7) -0.0043(5) 0.0050(5) 0.0002(5)
C11 0.0120(7) 0.0180(8) 0.0167(7) 0.0001(6) 0.0035(6) 0.0009(6)
C8 0.0123(7) 0.0142(7) 0.0182(8) 0.0018(6) 0.0033(6) -0.0008(6)
C12 0.0142(7) 0.0195(8) 0.0186(8) 0.0002(6) 0.0052(6) -0.0009(6)
C10 0.0134(7) 0.0157(7) 0.0156(7) -0.0011(6) 0.0039(6) 0.0010(6)
C20 0.0152(8) 0.0189(8) 0.0232(8) -0.0020(6) 0.0059(6) -0.0039(6)
C2 0.0156(8) 0.0170(8) 0.0198(8) 0.0026(6) 0.0064(6) -0.0005(6)
C7 0.0167(8) 0.0159(8) 0.0191(8) 0.0003(6) 0.0047(6) -0.0015(6)
C13 0.0161(8) 0.0190(8) 0.0199(8) 0.0003(6) 0.0062(6) -0.0022(6)
C16 0.0176(8) 0.0173(8) 0.0200(8) 0.0019(6) 0.0051(6) 0.0001(6)
C15 0.0136(7) 0.0166(8) 0.0172(7) 0.0008(6) 0.0037(6) 0.0016(6)
C14 0.0154(7) 0.0158(8) 0.0176(7) -0.0001(6) 0.0057(6) 0.0007(6)
C26 0.0255(9) 0.0211(8) 0.0211(8) 0.0000(7) 0.0054(7) 0.0002(7)
C22 0.0147(8) 0.0183(8) 0.0248(8) 0.0000(7) 0.0070(7) -0.0011(6)
C25 0.0144(7) 0.0198(8) 0.0178(8) 0.0033(6) 0.0050(6) 0.0004(6)
C17 0.0186(8) 0.0190(8) 0.0240(8) 0.0018(7) 0.0068(7) -0.0022(6)
C30 0.0166(8) 0.0199(8) 0.0217(8) 0.0024(7) 0.0079(6) -0.0001(6)
C6 0.0184(8) 0.0227(8) 0.0173(8) 0.0020(6) 0.0024(6) -0.0021(7)
C3 0.0144(8) 0.0219(8) 0.0269(9) 0.0048(7) 0.0080(7) 0.0032(6)
C19 0.0133(7) 0.0196(8) 0.0215(8) 0.0013(6) 0.0058(6) -0.0023(6)
C18 0.0143(7) 0.0173(8) 0.0212(8) -0.0015(6) 0.0061(6) -0.0022(6)
C1 0.0213(8) 0.0262(9) 0.0219(9) 0.0001(7) 0.0100(7) 0.0028(7)
C9 0.0223(8) 0.0246(9) 0.0215(8) -0.0033(7) 0.0070(7) 0.0021(7)
C28 0.0242(9) 0.0350(11) 0.0215(9) 0.0087(8) 0.0033(7) 0.0026(8)
C29 0.0217(9) 0.0225(9) 0.0273(9) 0.0079(7) 0.0078(7) 0.0039(7)
C24 0.0211(9) 0.0206(9) 0.0419(11) -0.0072(8) 0.0068(8) -0.0009(7)
C4 0.0143(8) 0.0235(9) 0.0254(9) 0.0074(7) 0.0030(7) 0.0006(6)
C27 0.0315(10) 0.0324(10) 0.0189(9) -0.0007(8) 0.0021(7) -0.0009(8)
C5 0.0177(9) 0.0485(13) 0.0304(10) 0.0139(9) 0.0018(8) 0.0059(9)
N2 0.0113(6) 0.0165(7) 0.0190(7) 0.0002(5) 0.0034(5) -0.0002(5)
N1 0.0126(6) 0.0155(6) 0.0173(7) 0.0016(5) 0.0034(5) 0.0008(5)
B1 0.0128(8) 0.0157(8) 0.0177(8) 0.0002(7) 0.0032(6) -0.0003(7)
F1 0.0131(5) 0.0190(5) 0.0220(5) 0.0027(4) 0.0039(4) 0.0025(4)
F2 0.0217(5) 0.0195(5) 0.0202(5) -0.0036(4) 0.0067(4) -0.0023(4)
O1 0.0321(7) 0.0154(6) 0.0233(6) 0.0010(5) 0.0080(5) 0.0003(5)
C31 0.0326(10) 0.0158(8) 0.0344(10) 0.0005(7) 0.0137(8) -0.0006(7)
Cl1 0.0363(3) 0.0560(4) 0.1167(7) 0.0355(5) 0.0170(4) 0.0013(3)
Cl2 0.0582(6) 0.267(2) 0.0991(8) -0.1272(11) 0.0064(5) 0.0167(8)
C32 0.0331(11) 0.0607(16) 0.0298(11) -0.0031(10) 0.0105(9) 0.0053(11)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O2 C22 1.367(2) . ?
O2 C24 1.427(2) . ?
C11 C10 1.390(2) . ?
C11 N1 1.396(2) . ?
C11 C12 1.412(2) . ?
C8 C7 1.404(2) . ?
C8 C2 1.406(2) . ?
C8 C10 1.493(2) . ?
C12 C13 1.372(2) . ?
C12 H1 0.9500 . ?
C10 C15 1.394(2) . ?
C20 C22 1.393(2) . ?
C20 C19 1.397(2) . ?
C20 H2 0.9500 . ?
C2 C3 1.396(2) . ?
C2 C1 1.511(2) . ?
C7 C6 1.394(2) . ?
C7 C9 1.510(2) . ?
C13 C14 1.417(2) . ?
C13 H3 0.9500 . ?
C16 C17 1.381(2) . ?
C16 C15 1.411(2) . ?
C16 H4 0.9500 . ?
C15 N2 1.398(2) . ?
C14 N1 1.356(2) . ?
C14 C25 1.476(2) . ?
C26 C27 1.389(3) . ?
C26 C25 1.396(2) . ?
C26 H5 0.9500 . ?
C22 C19 1.405(2) 3_666 ?
C25 C30 1.408(2) . ?
C17 C18 1.408(2) . ?
C17 H6 0.9500 . ?
C30 O1 1.360(2) . ?
C30 C29 1.396(2) . ?
C6 C4 1.392(3) . ?
C6 H7 0.9500 . ?
C3 C4 1.391(3) . ?
C3 H8 0.9500 . ?
C19 C22 1.405(2) 3_666 ?
C19 C18 1.476(2) . ?
C18 N2 1.360(2) . ?
C1 H12 0.9800 . ?
C1 H13 0.9800 . ?
C1 H14 0.9800 . ?
C9 H15 0.9800 . ?
C9 H16 0.9800 . ?
C9 H17 0.9800 . ?
C28 C27 1.383(3) . ?
C28 C29 1.387(3) . ?
C28 H9 0.9500 . ?
C29 H10 0.9500 . ?
C24 H18 0.9800 . ?
C24 H19 0.9800 . ?
C24 H20 0.9800 . ?
C4 C5 1.509(2) . ?
C27 H11 0.9500 . ?
C5 H21 0.9800 . ?
C5 H22 0.9800 . ?
C5 H23 0.9800 . ?
N2 B1 1.565(2) . ?
N1 B1 1.560(2) . ?
B1 F1 1.381(2) . ?
B1 F2 1.397(2) . ?
O1 C31 1.431(2) . ?
C31 H24 0.9800 . ?
C31 H25 0.9800 . ?
C31 H26 0.9800 . ?
Cl1 C32 1.744(3) . ?
Cl2 C32 1.717(3) . ?
C32 H27 0.9900 . ?
C32 H28 0.9900 . ?

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
C22 O2 C24 117.40(14) . . ?
C10 C11 N1 121.93(15) . . ?
C10 C11 C12 129.52(15) . . ?
N1 C11 C12 108.51(14) . . ?
C7 C8 C2 120.80(15) . . ?
C7 C8 C10 120.62(15) . . ?
C2 C8 C10 118.54(15) . . ?
C13 C12 C11 107.06(15) . . ?
C13 C12 H1 126.5 . . ?
C11 C12 H1 126.5 . . ?
C11 C10 C15 120.39(15) . . ?
C11 C10 C8 118.14(14) . . ?
C15 C10 C8 121.44(15) . . ?
C22 C20 C19 121.25(16) . . ?
C22 C20 H2 119.4 . . ?
C19 C20 H2 119.4 . . ?
C3 C2 C8 118.45(16) . . ?
C3 C2 C1 119.12(16) . . ?
C8 C2 C1 122.35(15) . . ?
C6 C7 C8 118.67(16) . . ?
C6 C7 C9 120.16(16) . . ?
C8 C7 C9 121.15(15) . . ?
C12 C13 C14 107.78(15) . . ?
C12 C13 H3 126.1 . . ?
C14 C13 H3 126.1 . . ?
C17 C16 C15 107.07(15) . . ?
C17 C16 H4 126.5 . . ?
C15 C16 H4 126.5 . . ?
C10 C15 N2 121.10(15) . . ?
C10 C15 C16 130.18(15) . . ?
N2 C15 C16 108.71(14) . . ?
N1 C14 C13 109.05(14) . . ?
N1 C14 C25 124.51(15) . . ?
C13 C14 C25 126.05(15) . . ?
C27 C26 C25 121.48(18) . . ?
C27 C26 H5 119.3 . . ?
C25 C26 H5 119.3 . . ?
O2 C22 C20 123.98(16) . . ?
O2 C22 C19 116.56(15) . 3_666 ?
C20 C22 C19 119.45(16) . 3_666 ?
C26 C25 C30 118.36(16) . . ?
C26 C25 C14 120.96(16) . . ?
C30 C25 C14 120.44(16) . . ?
C16 C17 C18 107.43(15) . . ?
C16 C17 H6 126.3 . . ?
C18 C17 H6 126.3 . . ?
O1 C30 C29 124.01(16) . . ?
O1 C30 C25 115.85(15) . . ?
C29 C30 C25 120.14(17) . . ?
C4 C6 C7 121.71(16) . . ?
C4 C6 H7 119.1 . . ?
C7 C6 H7 119.1 . . ?
C4 C3 C2 121.82(16) . . ?
C4 C3 H8 119.1 . . ?
C2 C3 H8 119.1 . . ?
C20 C19 C22 119.29(15) . 3_666 ?
C20 C19 C18 120.02(16) . . ?
C22 C19 C18 120.65(16) 3_666 . ?
N2 C18 C17 109.78(15) . . ?
N2 C18 C19 123.19(15) . . ?
C17 C18 C19 126.99(15) . . ?
C2 C1 H12 109.5 . . ?
C2 C1 H13 109.5 . . ?
H12 C1 H13 109.5 . . ?
C2 C1 H14 109.5 . . ?
H12 C1 H14 109.5 . . ?
H13 C1 H14 109.5 . . ?
C7 C9 H15 109.5 . . ?
C7 C9 H16 109.5 . . ?
H15 C9 H16 109.5 . . ?
C7 C9 H17 109.5 . . ?
H15 C9 H17 109.5 . . ?
H16 C9 H17 109.5 . . ?
C27 C28 C29 120.69(18) . . ?
C27 C28 H9 119.7 . . ?
C29 C28 H9 119.7 . . ?
C28 C29 C30 119.96(18) . . ?
C28 C29 H10 120.0 . . ?
C30 C29 H10 120.0 . . ?
O2 C24 H18 109.5 . . ?
O2 C24 H19 109.5 . . ?
H18 C24 H19 109.5 . . ?
O2 C24 H20 109.5 . . ?
H18 C24 H20 109.5 . . ?
H19 C24 H20 109.5 . . ?
C3 C4 C6 118.56(16) . . ?
C3 C4 C5 120.82(17) . . ?
C6 C4 C5 120.62(18) . . ?
C28 C27 C26 119.37(19) . . ?
C28 C27 H11 120.3 . . ?
C26 C27 H11 120.3 . . ?
C4 C5 H21 109.5 . . ?
C4 C5 H22 109.5 . . ?
H21 C5 H22 109.5 . . ?
C4 C5 H23 109.5 . . ?
H21 C5 H23 109.5 . . ?
H22 C5 H23 109.5 . . ?
C18 N2 C15 106.99(14) . . ?
C18 N2 B1 127.00(14) . . ?
C15 N2 B1 122.52(14) . . ?
C14 N1 C11 107.53(14) . . ?
C14 N1 B1 129.33(14) . . ?
C11 N1 B1 123.09(14) . . ?
F1 B1 F2 110.09(14) . . ?
F1 B1 N1 109.09(14) . . ?
F2 B1 N1 110.84(14) . . ?
F1 B1 N2 112.47(14) . . ?
F2 B1 N2 107.27(14) . . ?
N1 B1 N2 107.04(13) . . ?
C30 O1 C31 116.85(15) . . ?
O1 C31 H24 109.5 . . ?
O1 C31 H25 109.5 . . ?
H24 C31 H25 109.5 . . ?
O1 C31 H26 109.5 . . ?
H24 C31 H26 109.5 . . ?
H25 C31 H26 109.5 . . ?
Cl2 C32 Cl1 113.97(15) . . ?
Cl2 C32 H27 108.8 . . ?
Cl1 C32 H27 108.8 . . ?
Cl2 C32 H28 108.8 . . ?
Cl1 C32 H28 108.8 . . ?
H27 C32 H28 107.7 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C11 C12 C13 176.19(17) . . . . ?
N1 C11 C12 C13 -1.52(19) . . . . ?
N1 C11 C10 C15 9.2(2) . . . . ?
C12 C11 C10 C15 -168.23(17) . . . . ?
N1 C11 C10 C8 -168.87(15) . . . . ?
C12 C11 C10 C8 13.7(3) . . . . ?
C7 C8 C10 C11 -105.25(19) . . . . ?
C2 C8 C10 C11 72.4(2) . . . . ?
C7 C8 C10 C15 76.7(2) . . . . ?
C2 C8 C10 C15 -105.65(19) . . . . ?
C7 C8 C2 C3 0.9(2) . . . . ?
C10 C8 C2 C3 -176.73(15) . . . . ?
C7 C8 C2 C1 -175.80(16) . . . . ?
C10 C8 C2 C1 6.5(2) . . . . ?
C2 C8 C7 C6 -0.4(3) . . . . ?
C10 C8 C7 C6 177.16(15) . . . . ?
C2 C8 C7 C9 -178.52(16) . . . . ?
C10 C8 C7 C9 -0.9(2) . . . . ?
C11 C12 C13 C14 2.55(19) . . . . ?
C11 C10 C15 N2 -0.4(2) . . . . ?
C8 C10 C15 N2 177.62(15) . . . . ?
C11 C10 C15 C16 -178.85(17) . . . . ?
C8 C10 C15 C16 -0.8(3) . . . . ?
C17 C16 C15 C10 177.51(18) . . . . ?
C17 C16 C15 N2 -1.1(2) . . . . ?
C12 C13 C14 N1 -2.7(2) . . . . ?
C12 C13 C14 C25 170.26(16) . . . . ?
C24 O2 C22 C20 -0.9(3) . . . . ?
C24 O2 C22 C19 179.99(16) . . . 3_666 ?
C19 C20 C22 O2 -179.98(16) . . . . ?
C19 C20 C22 C19 -0.9(3) . . . 3_666 ?
C27 C26 C25 C30 0.2(3) . . . . ?
C27 C26 C25 C14 174.63(18) . . . . ?
N1 C14 C25 C26 46.9(2) . . . . ?
C13 C14 C25 C26 -125.0(2) . . . . ?
N1 C14 C25 C30 -138.73(17) . . . . ?
C13 C14 C25 C30 49.3(2) . . . . ?
C15 C16 C17 C18 0.4(2) . . . . ?
C26 C25 C30 O1 -179.83(15) . . . . ?
C14 C25 C30 O1 5.7(2) . . . . ?
C26 C25 C30 C29 -0.5(3) . . . . ?
C14 C25 C30 C29 -174.93(16) . . . . ?
C8 C7 C6 C4 -0.3(3) . . . . ?
C9 C7 C6 C4 177.77(17) . . . . ?
C8 C2 C3 C4 -0.7(3) . . . . ?
C1 C2 C3 C4 176.17(17) . . . . ?
C22 C20 C19 C22 0.9(3) . . . 3_666 ?
C22 C20 C19 C18 178.55(16) . . . . ?
C16 C17 C18 N2 0.4(2) . . . . ?
C16 C17 C18 C19 178.09(17) . . . . ?
C20 C19 C18 N2 55.6(2) . . . . ?
C22 C19 C18 N2 -126.81(19) 3_666 . . . ?
C20 C19 C18 C17 -121.8(2) . . . . ?
C22 C19 C18 C17 55.8(3) 3_666 . . . ?
C27 C28 C29 C30 -0.1(3) . . . . ?
O1 C30 C29 C28 179.73(17) . . . . ?
C25 C30 C29 C28 0.4(3) . . . . ?
C2 C3 C4 C6 -0.1(3) . . . . ?
C2 C3 C4 C5 -179.59(18) . . . . ?
C7 C6 C4 C3 0.6(3) . . . . ?
C7 C6 C4 C5 -179.90(18) . . . . ?
C29 C28 C27 C26 -0.2(3) . . . . ?
C25 C26 C27 C28 0.1(3) . . . . ?
C17 C18 N2 C15 -1.05(19) . . . . ?
C19 C18 N2 C15 -178.86(16) . . . . ?
C17 C18 N2 B1 -160.13(16) . . . . ?
C19 C18 N2 B1 22.1(3) . . . . ?
C10 C15 N2 C18 -177.43(15) . . . . ?
C16 C15 N2 C18 1.32(19) . . . . ?
C10 C15 N2 B1 -17.2(2) . . . . ?
C16 C15 N2 B1 161.56(15) . . . . ?
C13 C14 N1 C11 1.76(19) . . . . ?
C25 C14 N1 C11 -171.37(15) . . . . ?
C13 C14 N1 B1 -175.79(16) . . . . ?
C25 C14 N1 B1 11.1(3) . . . . ?
C10 C11 N1 C14 -178.09(15) . . . . ?
C12 C11 N1 C14 -0.17(18) . . . . ?
C10 C11 N1 B1 -0.3(2) . . . . ?
C12 C11 N1 B1 177.57(15) . . . . ?
C14 N1 B1 F1 41.1(2) . . . . ?
C11 N1 B1 F1 -136.08(15) . . . . ?
C14 N1 B1 F2 -80.2(2) . . . . ?
C11 N1 B1 F2 102.54(17) . . . . ?
C14 N1 B1 N2 163.07(15) . . . . ?
C11 N1 B1 N2 -14.1(2) . . . . ?
C18 N2 B1 F1 -61.4(2) . . . . ?
C15 N2 B1 F1 142.51(15) . . . . ?
C18 N2 B1 F2 59.8(2) . . . . ?
C15 N2 B1 F2 -96.30(17) . . . . ?
C18 N2 B1 N1 178.82(15) . . . . ?
C15 N2 B1 N1 22.7(2) . . . . ?
C29 C30 O1 C31 3.6(3) . . . . ?
C25 C30 O1 C31 -177.10(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.432
_refine_diff_density_min         -1.270
_refine_diff_density_rms         0.064