# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2007


data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Atsuhiro Osuka'
_publ_contact_author_address     
;
Department of Chemistry
Kyoto University
Graduate School of Science
kyoto
Kyoto
606-8502
JAPAN
;

_publ_contact_author_email       OSUKA@KUCHEM.KYOTO-U.AC.JP

_publ_section_title              
;
Complementary face-to-face dimer formation from
meso-aryl subporphyrins bearing a 2-carboxyl group
;
loop_
_publ_author_name
'Atsuhiro Osuka'
'Yasuhide Inokuma'

# Attachment 'structure_9.cif'

data_s-mix-di
_database_code_depnum_ccdc_archive 'CCDC 644925'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            
;
bis[(5,10-diphenyl-15-(4-(trans-2-
carboxystyryl)phenyl)subporphyrinato)boron(III)]
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C84 H52 B2 N6 O4, 2(C H2 Cl2)'
_chemical_formula_sum            'C86 H56 B2 Cl4 N6 O4'
_chemical_formula_weight         1400.79

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'
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   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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                   15.823(3)
_cell_length_b                   12.328(4)
_cell_length_c                   18.763(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.961(7)
_cell_angle_gamma                90.00
_cell_volume                     3370.0(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    19740
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1448
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9541
_exptl_absorpt_correction_T_max  0.9767
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25828
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_sigmaI/netI    0.0541
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5920
_reflns_number_gt                4137
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0816P)^2^+4.0186P] 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         5920
_refine_ls_number_parameters     461
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1773
_refine_ls_wR_factor_gt          0.1577
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_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
C1 C 0.7254(2) 0.3251(3) 0.46483(19) 0.0283(8) Uani 1 1 d . . .
C2 C 0.6843(2) 0.4035(3) 0.4969(2) 0.0323(8) Uani 1 1 d . . .
H1 H 0.7162 0.4508 0.5388 0.039 Uiso 1 1 calc R . .
C3 C 0.5917(2) 0.3996(3) 0.4576(2) 0.0296(8) Uani 1 1 d . . .
H2 H 0.5479 0.4431 0.4674 0.036 Uiso 1 1 calc R . .
C4 C 0.5719(2) 0.3184(3) 0.39884(19) 0.0250(7) Uani 1 1 d . . .
C5 C 0.4908(2) 0.2583(3) 0.35741(18) 0.0246(7) Uani 1 1 d . . .
C6 C 0.5001(2) 0.1540(3) 0.33056(18) 0.0230(7) Uani 1 1 d . . .
C7 C 0.4420(2) 0.0601(3) 0.30626(19) 0.0266(8) Uani 1 1 d . . .
H3 H 0.3774 0.0592 0.2924 0.032 Uiso 1 1 calc R . .
C8 C 0.4948(2) -0.0273(3) 0.30649(19) 0.0255(7) Uani 1 1 d . . .
H4 H 0.4732 -0.0992 0.2921 0.031 Uiso 1 1 calc R . .
C9 C 0.5882(2) 0.0075(3) 0.33204(18) 0.0231(7) Uani 1 1 d . . .
C10 C 0.6744(2) -0.0441(3) 0.36078(18) 0.0245(7) Uani 1 1 d . . .
C11 C 0.7539(2) 0.0173(3) 0.40091(19) 0.0258(7) Uani 1 1 d . . .
C12 C 0.8423(2) -0.0097(3) 0.4571(2) 0.0304(8) Uani 1 1 d . . .
H5 H 0.8685 -0.0803 0.4661 0.036 Uiso 1 1 calc R . .
C13 C 0.8832(2) 0.0820(3) 0.4957(2) 0.0310(8) Uani 1 1 d . . .
H6 H 0.9428 0.0866 0.5356 0.037 Uiso 1 1 calc R . .
C14 C 0.8204(2) 0.1705(3) 0.46564(19) 0.0272(8) Uani 1 1 d . . .
C15 C 0.8121(2) 0.2738(3) 0.49409(19) 0.0289(8) Uani 1 1 d . . .
C16 C 0.4018(2) 0.3002(3) 0.35528(19) 0.0273(8) Uani 1 1 d . . .
C17 C 0.3766(2) 0.4069(3) 0.3334(2) 0.0325(8) Uani 1 1 d . . .
H7 H 0.4167 0.4524 0.3201 0.039 Uiso 1 1 calc R . .
C18 C 0.2940(3) 0.4478(3) 0.3308(2) 0.0410(10) Uani 1 1 d . . .
H8 H 0.2769 0.5205 0.3149 0.049 Uiso 1 1 calc R . .
C19 C 0.2364(3) 0.3819(4) 0.3514(2) 0.0473(11) Uani 1 1 d . . .
H9 H 0.1790 0.4090 0.3487 0.057 Uiso 1 1 calc R . .
C20 C 0.2619(3) 0.2776(4) 0.3756(3) 0.0462(11) Uani 1 1 d . . .
H10 H 0.2232 0.2335 0.3915 0.055 Uiso 1 1 calc R . .
C21 C 0.3443(2) 0.2363(3) 0.3771(2) 0.0362(9) Uani 1 1 d . . .
H11 H 0.3611 0.1636 0.3933 0.043 Uiso 1 1 calc R . .
C22 C 0.6826(2) -0.1639(3) 0.36400(19) 0.0264(8) Uani 1 1 d . . .
C23 C 0.6292(3) -0.2258(3) 0.3920(2) 0.0356(9) Uani 1 1 d . . .
H12 H 0.5850 -0.1911 0.4069 0.043 Uiso 1 1 calc R . .
C24 C 0.6392(3) -0.3369(3) 0.3987(2) 0.0427(10) Uani 1 1 d . . .
H13 H 0.6011 -0.3782 0.4170 0.051 Uiso 1 1 calc R . .
C25 C 0.7044(3) -0.3879(3) 0.3789(2) 0.0423(10) Uani 1 1 d . . .
H14 H 0.7116 -0.4644 0.3837 0.051 Uiso 1 1 calc R . .
C26 C 0.7585(3) -0.3278(3) 0.3523(2) 0.0390(9) Uani 1 1 d . . .
H15 H 0.8040 -0.3629 0.3392 0.047 Uiso 1 1 calc R . .
C27 C 0.7481(2) -0.2167(3) 0.3442(2) 0.0327(8) Uani 1 1 d . . .
H16 H 0.7859 -0.1762 0.3251 0.039 Uiso 1 1 calc R . .
C28 C 0.8884(2) 0.3226(3) 0.5596(2) 0.0318(8) Uani 1 1 d . . .
C29 C 0.9371(2) 0.2653(3) 0.6273(2) 0.0358(9) Uani 1 1 d . . .
H17 H 0.9202 0.1928 0.6327 0.043 Uiso 1 1 calc R . .
C30 C 1.0095(3) 0.3126(4) 0.6864(2) 0.0404(10) Uani 1 1 d . . .
H18 H 1.0422 0.2720 0.7319 0.048 Uiso 1 1 calc R . .
C31 C 1.0356(2) 0.4185(4) 0.6805(2) 0.0409(10) Uani 1 1 d DU . .
C32 C 0.9871(3) 0.4768(4) 0.6136(3) 0.0464(11) Uani 1 1 d . . .
H19 H 1.0040 0.5496 0.6090 0.056 Uiso 1 1 calc R . .
C33 C 0.9147(2) 0.4298(3) 0.5537(2) 0.0384(9) Uani 1 1 d . . .
H20 H 0.8823 0.4704 0.5082 0.046 Uiso 1 1 calc R . .
C34 C 1.1131(3) 0.4635(4) 0.7422(3) 0.0559(12) Uani 1 1 d DU . .
H21 H 1.1388 0.4081 0.7797 0.067 Uiso 1 1 calc R . .
C35 C 1.1603(3) 0.5477(3) 0.7662(2) 0.0471(11) Uani 1 1 d DU . .
H22 H 1.1302 0.6058 0.7325 0.056 Uiso 1 1 calc R . .
C36 C 1.2425(2) 0.5892(3) 0.8252(2) 0.0315(8) Uani 1 1 d DU . .
C37 C 1.2693(3) 0.5508(3) 0.8996(2) 0.0418(10) Uani 1 1 d . . .
H23 H 1.2324 0.4985 0.9112 0.050 Uiso 1 1 calc R . .
C38 C 0.6515(3) 0.4131(3) 0.0424(2) 0.0431(10) Uani 1 1 d . . .
H24 H 0.6333 0.4423 -0.0082 0.052 Uiso 1 1 calc R . .
C39 C 0.5980(3) 0.3346(3) 0.0571(2) 0.0370(9) Uani 1 1 d . . .
H25 H 0.5436 0.3090 0.0169 0.044 Uiso 1 1 calc R . .
C40 C 0.6248(2) 0.2938(3) 0.13136(19) 0.0275(8) Uani 1 1 d . . .
H26 H 0.5891 0.2386 0.1416 0.033 Uiso 1 1 calc R . .
C41 C 0.7028(2) 0.3320(3) 0.19121(19) 0.0244(7) Uani 1 1 d . . .
C42 C 0.7229(2) 0.2967(3) 0.27249(19) 0.0247(7) Uani 1 1 d . . .
B1 B 0.6652(2) 0.1908(3) 0.3550(2) 0.0229(8) Uani 1 1 d . . .
N1 N 0.65511(18) 0.2819(2) 0.40266(15) 0.0246(6) Uani 1 1 d . . .
N2 N 0.58524(18) 0.1185(2) 0.33992(15) 0.0231(6) Uani 1 1 d . . .
N3 N 0.74737(18) 0.1284(2) 0.40445(15) 0.0247(6) Uani 1 1 d . . .
O1 O 0.66369(15) 0.22433(18) 0.27743(12) 0.0254(5) Uani 1 1 d . . .
O2 O 0.78535(17) 0.3322(2) 0.32821(14) 0.0387(6) Uani 1 1 d . . .
C43 C 0.9226(3) 0.1384(4) 0.3257(3) 0.0607(14) Uani 1 1 d . . .
H27 H 0.8744 0.1466 0.3467 0.073 Uiso 1 1 calc R . .
H28 H 0.9005 0.1742 0.2745 0.073 Uiso 1 1 calc R . .
Cl1 Cl 0.93917(8) 0.00218(11) 0.31429(7) 0.0592(4) Uani 1 1 d . . .
Cl2 Cl 1.02437(9) 0.20427(11) 0.38878(7) 0.0655(4) Uani 1 1 d . . .

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
C1 0.0335(19) 0.0235(19) 0.0265(19) -0.0013(15) 0.0101(16) -0.0091(15)
C2 0.043(2) 0.0236(19) 0.031(2) -0.0064(16) 0.0142(18) -0.0097(16)
C3 0.038(2) 0.0216(19) 0.0300(19) -0.0016(15) 0.0138(17) -0.0022(15)
C4 0.0300(18) 0.0193(17) 0.0259(18) 0.0044(14) 0.0110(15) 0.0007(14)
C5 0.0294(18) 0.0214(18) 0.0218(17) 0.0029(14) 0.0086(15) -0.0005(14)
C6 0.0244(16) 0.0243(19) 0.0182(16) 0.0022(14) 0.0061(14) 0.0012(14)
C7 0.0236(17) 0.0276(19) 0.0270(18) -0.0002(15) 0.0080(15) -0.0024(15)
C8 0.0282(18) 0.0222(18) 0.0254(18) -0.0024(14) 0.0097(15) -0.0066(14)
C9 0.0307(18) 0.0201(18) 0.0189(16) 0.0007(13) 0.0100(15) -0.0026(14)
C10 0.0301(18) 0.0241(19) 0.0207(17) 0.0018(14) 0.0115(15) -0.0024(14)
C11 0.0305(18) 0.0244(19) 0.0246(18) 0.0015(15) 0.0129(16) -0.0001(15)
C12 0.0309(18) 0.030(2) 0.0301(19) 0.0048(16) 0.0120(16) 0.0052(16)
C13 0.0256(18) 0.039(2) 0.0244(18) 0.0019(16) 0.0054(15) -0.0016(16)
C14 0.0262(17) 0.031(2) 0.0231(17) 0.0006(15) 0.0076(15) -0.0044(15)
C15 0.0312(19) 0.032(2) 0.0205(17) 0.0000(15) 0.0072(15) -0.0068(15)
C16 0.0266(17) 0.029(2) 0.0234(17) -0.0046(15) 0.0064(15) -0.0004(15)
C17 0.0338(19) 0.034(2) 0.0263(19) -0.0041(16) 0.0084(16) 0.0032(16)
C18 0.045(2) 0.034(2) 0.039(2) -0.0063(18) 0.0108(19) 0.0113(19)
C19 0.036(2) 0.054(3) 0.052(3) -0.020(2) 0.016(2) 0.003(2)
C20 0.038(2) 0.046(3) 0.059(3) -0.013(2) 0.023(2) -0.0089(19)
C21 0.035(2) 0.032(2) 0.041(2) -0.0044(17) 0.0148(18) -0.0034(17)
C22 0.0291(18) 0.0237(19) 0.0221(17) 0.0013(14) 0.0051(15) 0.0010(15)
C23 0.042(2) 0.027(2) 0.042(2) 0.0051(17) 0.0213(19) 0.0017(16)
C24 0.052(2) 0.027(2) 0.052(3) 0.0067(19) 0.023(2) -0.0004(18)
C25 0.054(2) 0.023(2) 0.044(2) 0.0015(18) 0.013(2) 0.0027(18)
C26 0.045(2) 0.033(2) 0.037(2) -0.0018(18) 0.0142(19) 0.0125(18)
C27 0.035(2) 0.029(2) 0.035(2) -0.0001(16) 0.0146(17) 0.0021(16)
C28 0.0290(18) 0.034(2) 0.031(2) -0.0078(16) 0.0098(16) -0.0067(16)
C29 0.034(2) 0.043(2) 0.027(2) -0.0037(17) 0.0087(17) -0.0120(17)
C30 0.036(2) 0.055(3) 0.029(2) -0.0012(19) 0.0118(18) -0.0061(19)
C31 0.0279(19) 0.058(3) 0.037(2) -0.018(2) 0.0130(18) -0.0108(18)
C32 0.036(2) 0.041(2) 0.062(3) -0.015(2) 0.019(2) -0.0128(19)
C33 0.033(2) 0.036(2) 0.041(2) -0.0057(18) 0.0073(18) -0.0065(17)
C34 0.043(2) 0.077(3) 0.056(3) -0.030(2) 0.027(2) -0.015(2)
C35 0.069(3) 0.037(2) 0.057(3) -0.0141(19) 0.049(2) -0.018(2)
C36 0.045(2) 0.0223(19) 0.038(2) -0.0060(16) 0.0284(18) -0.0052(16)
C37 0.071(3) 0.026(2) 0.047(2) -0.0004(18) 0.042(2) -0.0026(19)
C38 0.075(3) 0.033(2) 0.031(2) 0.0054(18) 0.031(2) 0.010(2)
C39 0.049(2) 0.038(2) 0.0236(19) -0.0034(17) 0.0131(18) 0.0083(18)
C40 0.0317(18) 0.0234(19) 0.0284(19) -0.0026(15) 0.0128(16) 0.0003(15)
C41 0.0288(17) 0.0196(18) 0.0283(18) -0.0011(14) 0.0150(15) 0.0006(14)
C42 0.0247(17) 0.0199(18) 0.0281(19) -0.0031(15) 0.0088(16) -0.0042(14)
B1 0.0245(19) 0.021(2) 0.0222(19) -0.0018(15) 0.0080(16) -0.0035(15)
N1 0.0276(15) 0.0213(15) 0.0219(14) -0.0006(12) 0.0065(12) -0.0037(12)
N2 0.0283(15) 0.0190(15) 0.0210(14) -0.0007(12) 0.0086(12) -0.0022(12)
N3 0.0272(14) 0.0235(16) 0.0227(15) -0.0022(12) 0.0089(12) -0.0042(12)
O1 0.0287(12) 0.0227(13) 0.0232(12) -0.0005(10) 0.0085(10) -0.0063(10)
O2 0.0337(13) 0.0436(16) 0.0303(14) 0.0044(12) 0.0033(12) -0.0144(13)
C43 0.049(3) 0.088(4) 0.053(3) 0.026(3) 0.027(2) 0.019(3)
Cl1 0.0541(7) 0.0722(9) 0.0531(7) 0.0033(6) 0.0228(6) -0.0018(6)
Cl2 0.0754(8) 0.0618(8) 0.0592(8) 0.0088(6) 0.0262(7) 0.0015(6)

_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
C1 N1 1.367(4) . ?
C1 C15 1.412(5) . ?
C1 C2 1.424(5) . ?
C2 C3 1.360(5) . ?
C2 H1 0.9500 . ?
C3 C4 1.430(5) . ?
C3 H2 0.9500 . ?
C4 N1 1.367(4) . ?
C4 C5 1.420(5) . ?
C5 C6 1.409(5) . ?
C5 C16 1.486(5) . ?
C6 N2 1.362(4) . ?
C6 C7 1.437(5) . ?
C7 C8 1.363(5) . ?
C7 H3 0.9500 . ?
C8 C9 1.431(4) . ?
C8 H4 0.9500 . ?
C9 N2 1.379(4) . ?
C9 C10 1.408(5) . ?
C10 C11 1.408(5) . ?
C10 C22 1.482(5) . ?
C11 N3 1.377(4) . ?
C11 C12 1.423(5) . ?
C12 C13 1.363(5) . ?
C12 H5 0.9500 . ?
C13 C14 1.435(5) . ?
C13 H6 0.9500 . ?
C14 N3 1.374(4) . ?
C14 C15 1.406(5) . ?
C15 C28 1.474(5) . ?
C16 C21 1.382(5) . ?
C16 C17 1.389(5) . ?
C17 C18 1.384(5) . ?
C17 H7 0.9500 . ?
C18 C19 1.384(6) . ?
C18 H8 0.9500 . ?
C19 C20 1.371(6) . ?
C19 H9 0.9500 . ?
C20 C21 1.389(5) . ?
C20 H10 0.9500 . ?
C21 H11 0.9500 . ?
C22 C23 1.385(5) . ?
C22 C27 1.392(5) . ?
C23 C24 1.378(5) . ?
C23 H12 0.9500 . ?
C24 C25 1.377(6) . ?
C24 H13 0.9500 . ?
C25 C26 1.367(6) . ?
C25 H14 0.9500 . ?
C26 C27 1.380(5) . ?
C26 H15 0.9500 . ?
C27 H16 0.9500 . ?
C28 C29 1.395(5) . ?
C28 C33 1.402(5) . ?
C29 C30 1.375(5) . ?
C29 H17 0.9500 . ?
C30 C31 1.386(6) . ?
C30 H18 0.9500 . ?
C31 C32 1.389(6) . ?
C31 C34 1.429(4) . ?
C32 C33 1.381(5) . ?
C32 H19 0.9500 . ?
C33 H20 0.9500 . ?
C34 C35 1.255(4) . ?
C34 H21 0.9500 . ?
C35 C36 1.434(4) . ?
C35 H22 0.9500 . ?
C36 C37 1.376(5) . ?
C36 C41 1.413(5) 3_766 ?
C37 C38 1.374(6) 3_766 ?
C37 H23 0.9500 . ?
C38 C37 1.374(6) 3_766 ?
C38 C39 1.383(6) . ?
C38 H24 0.9500 . ?
C39 C40 1.382(5) . ?
C39 H25 0.9500 . ?
C40 C41 1.387(5) . ?
C40 H26 0.9500 . ?
C41 C36 1.413(5) 3_766 ?
C41 C42 1.496(5) . ?
C42 O2 1.206(4) . ?
C42 O1 1.323(4) . ?
B1 N2 1.482(4) . ?
B1 N1 1.482(5) . ?
B1 N3 1.483(5) . ?
B1 O1 1.505(4) . ?
C43 Cl1 1.726(5) . ?
C43 Cl2 1.780(5) . ?
C43 H27 0.9900 . ?
C43 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
N1 C1 C15 120.1(3) . . ?
N1 C1 C2 105.7(3) . . ?
C15 C1 C2 132.4(3) . . ?
C3 C2 C1 108.6(3) . . ?
C3 C2 H1 125.7 . . ?
C1 C2 H1 125.7 . . ?
C2 C3 C4 108.0(3) . . ?
C2 C3 H2 126.0 . . ?
C4 C3 H2 126.0 . . ?
N1 C4 C5 120.2(3) . . ?
N1 C4 C3 105.8(3) . . ?
C5 C4 C3 131.8(3) . . ?
C6 C5 C4 118.3(3) . . ?
C6 C5 C16 122.5(3) . . ?
C4 C5 C16 118.5(3) . . ?
N2 C6 C5 118.9(3) . . ?
N2 C6 C7 105.1(3) . . ?
C5 C6 C7 134.9(3) . . ?
C8 C7 C6 108.7(3) . . ?
C8 C7 H3 125.7 . . ?
C6 C7 H3 125.7 . . ?
C7 C8 C9 108.4(3) . . ?
C7 C8 H4 125.8 . . ?
C9 C8 H4 125.8 . . ?
N2 C9 C10 118.4(3) . . ?
N2 C9 C8 105.0(3) . . ?
C10 C9 C8 135.5(3) . . ?
C9 C10 C11 119.5(3) . . ?
C9 C10 C22 121.5(3) . . ?
C11 C10 C22 117.9(3) . . ?
N3 C11 C10 119.5(3) . . ?
N3 C11 C12 105.5(3) . . ?
C10 C11 C12 133.2(3) . . ?
C13 C12 C11 109.0(3) . . ?
C13 C12 H5 125.5 . . ?
C11 C12 H5 125.5 . . ?
C12 C13 C14 108.0(3) . . ?
C12 C13 H6 126.0 . . ?
C14 C13 H6 126.0 . . ?
N3 C14 C15 119.2(3) . . ?
N3 C14 C13 105.6(3) . . ?
C15 C14 C13 133.8(3) . . ?
C14 C15 C1 118.5(3) . . ?
C14 C15 C28 121.3(3) . . ?
C1 C15 C28 119.8(3) . . ?
C21 C16 C17 118.7(3) . . ?
C21 C16 C5 121.4(3) . . ?
C17 C16 C5 119.8(3) . . ?
C18 C17 C16 120.9(4) . . ?
C18 C17 H7 119.5 . . ?
C16 C17 H7 119.5 . . ?
C19 C18 C17 119.5(4) . . ?
C19 C18 H8 120.3 . . ?
C17 C18 H8 120.3 . . ?
C20 C19 C18 120.1(4) . . ?
C20 C19 H9 120.0 . . ?
C18 C19 H9 120.0 . . ?
C19 C20 C21 120.3(4) . . ?
C19 C20 H10 119.9 . . ?
C21 C20 H10 119.9 . . ?
C16 C21 C20 120.4(4) . . ?
C16 C21 H11 119.8 . . ?
C20 C21 H11 119.8 . . ?
C23 C22 C27 118.1(3) . . ?
C23 C22 C10 120.6(3) . . ?
C27 C22 C10 121.1(3) . . ?
C24 C23 C22 121.1(3) . . ?
C24 C23 H12 119.4 . . ?
C22 C23 H12 119.4 . . ?
C25 C24 C23 120.0(4) . . ?
C25 C24 H13 120.0 . . ?
C23 C24 H13 120.0 . . ?
C26 C25 C24 119.6(4) . . ?
C26 C25 H14 120.2 . . ?
C24 C25 H14 120.2 . . ?
C25 C26 C27 120.9(4) . . ?
C25 C26 H15 119.6 . . ?
C27 C26 H15 119.6 . . ?
C26 C27 C22 120.3(3) . . ?
C26 C27 H16 119.9 . . ?
C22 C27 H16 119.9 . . ?
C29 C28 C33 118.2(3) . . ?
C29 C28 C15 122.3(3) . . ?
C33 C28 C15 119.4(3) . . ?
C30 C29 C28 120.7(4) . . ?
C30 C29 H17 119.6 . . ?
C28 C29 H17 119.6 . . ?
C29 C30 C31 121.0(4) . . ?
C29 C30 H18 119.5 . . ?
C31 C30 H18 119.5 . . ?
C30 C31 C32 118.8(3) . . ?
C30 C31 C34 119.3(4) . . ?
C32 C31 C34 121.9(4) . . ?
C33 C32 C31 120.6(4) . . ?
C33 C32 H19 119.7 . . ?
C31 C32 H19 119.7 . . ?
C32 C33 C28 120.6(4) . . ?
C32 C33 H20 119.7 . . ?
C28 C33 H20 119.7 . . ?
C35 C34 C31 144.4(5) . . ?
C35 C34 H21 107.8 . . ?
C31 C34 H21 107.8 . . ?
C34 C35 C36 143.6(5) . . ?
C34 C35 H22 108.2 . . ?
C36 C35 H22 108.2 . . ?
C37 C36 C41 119.0(3) . 3_766 ?
C37 C36 C35 119.3(3) . . ?
C41 C36 C35 121.7(3) 3_766 . ?
C38 C37 C36 121.1(4) 3_766 . ?
C38 C37 H23 119.5 3_766 . ?
C36 C37 H23 119.5 . . ?
C37 C38 C39 120.6(4) 3_766 . ?
C37 C38 H24 119.7 3_766 . ?
C39 C38 H24 119.7 . . ?
C40 C39 C38 119.0(4) . . ?
C40 C39 H25 120.5 . . ?
C38 C39 H25 120.5 . . ?
C39 C40 C41 121.2(3) . . ?
C39 C40 H26 119.4 . . ?
C41 C40 H26 119.4 . . ?
C40 C41 C36 119.0(3) . 3_766 ?
C40 C41 C42 119.7(3) . . ?
C36 C41 C42 121.1(3) 3_766 . ?
O2 C42 O1 123.2(3) . . ?
O2 C42 C41 123.7(3) . . ?
O1 C42 C41 113.1(3) . . ?
N2 B1 N1 106.6(3) . . ?
N2 B1 N3 106.4(3) . . ?
N1 B1 N3 106.9(3) . . ?
N2 B1 O1 106.8(3) . . ?
N1 B1 O1 114.2(3) . . ?
N3 B1 O1 115.3(3) . . ?
C1 N1 C4 111.3(3) . . ?
C1 N1 B1 124.5(3) . . ?
C4 N1 B1 123.1(3) . . ?
C6 N2 C9 112.3(3) . . ?
C6 N2 B1 124.0(3) . . ?
C9 N2 B1 123.7(3) . . ?
C14 N3 C11 111.2(3) . . ?
C14 N3 B1 124.9(3) . . ?
C11 N3 B1 123.3(3) . . ?
C42 O1 B1 120.6(3) . . ?
Cl1 C43 Cl2 112.6(2) . . ?
Cl1 C43 H27 109.1 . . ?
Cl2 C43 H27 109.1 . . ?
Cl1 C43 H28 109.1 . . ?
Cl2 C43 H28 109.1 . . ?
H27 C43 H28 107.8 . . ?

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
N1 C1 C2 C3 4.5(4) . . . . ?
C15 C1 C2 C3 -159.8(4) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 N1 -3.8(4) . . . . ?
C2 C3 C4 C5 158.7(4) . . . . ?
N1 C4 C5 C6 9.1(5) . . . . ?
C3 C4 C5 C6 -151.4(4) . . . . ?
N1 C4 C5 C16 179.4(3) . . . . ?
C3 C4 C5 C16 19.0(5) . . . . ?
C4 C5 C6 N2 -5.1(4) . . . . ?
C16 C5 C6 N2 -175.0(3) . . . . ?
C4 C5 C6 C7 160.4(4) . . . . ?
C16 C5 C6 C7 -9.5(6) . . . . ?
N2 C6 C7 C8 3.5(4) . . . . ?
C5 C6 C7 C8 -163.4(4) . . . . ?
C6 C7 C8 C9 0.9(4) . . . . ?
C7 C8 C9 N2 -4.9(4) . . . . ?
C7 C8 C9 C10 162.5(4) . . . . ?
N2 C9 C10 C11 4.1(4) . . . . ?
C8 C9 C10 C11 -161.9(3) . . . . ?
N2 C9 C10 C22 171.7(3) . . . . ?
C8 C9 C10 C22 5.6(6) . . . . ?
C9 C10 C11 N3 -6.7(5) . . . . ?
C22 C10 C11 N3 -174.7(3) . . . . ?
C9 C10 C11 C12 155.5(3) . . . . ?
C22 C10 C11 C12 -12.5(5) . . . . ?
N3 C11 C12 C13 4.1(4) . . . . ?
C10 C11 C12 C13 -159.9(4) . . . . ?
C11 C12 C13 C14 1.0(4) . . . . ?
C12 C13 C14 N3 -5.7(4) . . . . ?
C12 C13 C14 C15 159.7(4) . . . . ?
N3 C14 C15 C1 7.5(5) . . . . ?
C13 C14 C15 C1 -156.4(4) . . . . ?
N3 C14 C15 C28 -180.0(3) . . . . ?
C13 C14 C15 C28 16.1(6) . . . . ?
N1 C1 C15 C14 -9.2(5) . . . . ?
C2 C1 C15 C14 153.2(4) . . . . ?
N1 C1 C15 C28 178.1(3) . . . . ?
C2 C1 C15 C28 -19.5(6) . . . . ?
C6 C5 C16 C21 43.6(5) . . . . ?
C4 C5 C16 C21 -126.3(4) . . . . ?
C6 C5 C16 C17 -138.6(3) . . . . ?
C4 C5 C16 C17 51.5(4) . . . . ?
C21 C16 C17 C18 -2.3(5) . . . . ?
C5 C16 C17 C18 179.8(3) . . . . ?
C16 C17 C18 C19 1.1(6) . . . . ?
C17 C18 C19 C20 1.2(6) . . . . ?
C18 C19 C20 C21 -2.2(6) . . . . ?
C17 C16 C21 C20 1.3(5) . . . . ?
C5 C16 C21 C20 179.2(3) . . . . ?
C19 C20 C21 C16 0.9(6) . . . . ?
C9 C10 C22 C23 -45.6(5) . . . . ?
C11 C10 C22 C23 122.1(4) . . . . ?
C9 C10 C22 C27 139.0(3) . . . . ?
C11 C10 C22 C27 -53.3(4) . . . . ?
C27 C22 C23 C24 -1.3(6) . . . . ?
C10 C22 C23 C24 -176.9(4) . . . . ?
C22 C23 C24 C25 1.3(6) . . . . ?
C23 C24 C25 C26 -0.3(6) . . . . ?
C24 C25 C26 C27 -0.7(6) . . . . ?
C25 C26 C27 C22 0.7(6) . . . . ?
C23 C22 C27 C26 0.3(5) . . . . ?
C10 C22 C27 C26 175.9(3) . . . . ?
C14 C15 C28 C29 -47.1(5) . . . . ?
C1 C15 C28 C29 125.3(4) . . . . ?
C14 C15 C28 C33 131.6(4) . . . . ?
C1 C15 C28 C33 -56.0(5) . . . . ?
C33 C28 C29 C30 -0.5(5) . . . . ?
C15 C28 C29 C30 178.2(3) . . . . ?
C28 C29 C30 C31 0.4(6) . . . . ?
C29 C30 C31 C32 0.1(6) . . . . ?
C29 C30 C31 C34 -178.0(4) . . . . ?
C30 C31 C32 C33 -0.5(6) . . . . ?
C34 C31 C32 C33 177.6(4) . . . . ?
C31 C32 C33 C28 0.4(6) . . . . ?
C29 C28 C33 C32 0.1(5) . . . . ?
C15 C28 C33 C32 -178.7(3) . . . . ?
C30 C31 C34 C35 -176.8(6) . . . . ?
C32 C31 C34 C35 5.2(9) . . . . ?
C31 C34 C35 C36 -172.3(5) . . . . ?
C34 C35 C36 C37 -37.6(8) . . . . ?
C34 C35 C36 C41 141.9(5) . . . 3_766 ?
C41 C36 C37 C38 -0.7(6) 3_766 . . 3_766 ?
C35 C36 C37 C38 178.8(4) . . . 3_766 ?
C37 C38 C39 C40 0.8(6) 3_766 . . . ?
C38 C39 C40 C41 1.5(5) . . . . ?
C39 C40 C41 C36 -2.7(5) . . . 3_766 ?
C39 C40 C41 C42 172.0(3) . . . . ?
C40 C41 C42 O2 -174.4(3) . . . . ?
C36 C41 C42 O2 0.2(5) 3_766 . . . ?
C40 C41 C42 O1 4.0(4) . . . . ?
C36 C41 C42 O1 178.6(3) 3_766 . . . ?
C15 C1 N1 C4 159.5(3) . . . . ?
C2 C1 N1 C4 -7.1(4) . . . . ?
C15 C1 N1 B1 -8.6(5) . . . . ?
C2 C1 N1 B1 -175.3(3) . . . . ?
C5 C4 N1 C1 -158.1(3) . . . . ?
C3 C4 N1 C1 6.9(4) . . . . ?
C5 C4 N1 B1 10.3(5) . . . . ?
C3 C4 N1 B1 175.2(3) . . . . ?
N2 B1 N1 C1 137.8(3) . . . . ?
N3 B1 N1 C1 24.3(4) . . . . ?
O1 B1 N1 C1 -104.4(3) . . . . ?
N2 B1 N1 C4 -29.0(4) . . . . ?
N3 B1 N1 C4 -142.5(3) . . . . ?
O1 B1 N1 C4 88.7(4) . . . . ?
C5 C6 N2 C9 162.6(3) . . . . ?
C7 C6 N2 C9 -6.8(4) . . . . ?
C5 C6 N2 B1 -18.7(5) . . . . ?
C7 C6 N2 B1 171.9(3) . . . . ?
C10 C9 N2 C6 -162.6(3) . . . . ?
C8 C9 N2 C6 7.4(3) . . . . ?
C10 C9 N2 B1 18.7(4) . . . . ?
C8 C9 N2 B1 -171.3(3) . . . . ?
N1 B1 N2 C6 33.7(4) . . . . ?
N3 B1 N2 C6 147.6(3) . . . . ?
O1 B1 N2 C6 -88.8(3) . . . . ?
N1 B1 N2 C9 -147.7(3) . . . . ?
N3 B1 N2 C9 -33.9(4) . . . . ?
O1 B1 N2 C9 89.8(4) . . . . ?
C15 C14 N3 C11 -159.5(3) . . . . ?
C13 C14 N3 C11 8.5(4) . . . . ?
C15 C14 N3 B1 12.3(5) . . . . ?
C13 C14 N3 B1 -179.7(3) . . . . ?
C10 C11 N3 C14 158.8(3) . . . . ?
C12 C11 N3 C14 -7.9(4) . . . . ?
C10 C11 N3 B1 -13.2(5) . . . . ?
C12 C11 N3 B1 -179.9(3) . . . . ?
N2 B1 N3 C14 -140.0(3) . . . . ?
N1 B1 N3 C14 -26.3(4) . . . . ?
O1 B1 N3 C14 101.8(3) . . . . ?
N2 B1 N3 C11 30.9(4) . . . . ?
N1 B1 N3 C11 144.5(3) . . . . ?
O1 B1 N3 C11 -87.3(4) . . . . ?
O2 C42 O1 B1 6.8(5) . . . . ?
C41 C42 O1 B1 -171.6(3) . . . . ?
N2 B1 O1 C42 174.3(3) . . . . ?
N1 B1 O1 C42 56.7(4) . . . . ?
N3 B1 O1 C42 -67.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.065