# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_wakabayashi_methoxy

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            
'Cyclic Trimer of 3-(Diethylborylethynyl)pyridine'
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H48 B3 N3 O3'
_chemical_formula_sum            'C36 H48 B3 N3 O3'
_chemical_formula_weight         603.20
_publ_section_abstract_2         
'Self-Assembly via B-N Coordination Imparts Conformational Flexibility'
_publ_author_name_2              'Kuse, M.'
_publ_author_name_3              'Kida, A.'
_publ_author_name_4              'Komeda, S.'
_publ_author_name_5              'Tatsumi, K.'
_publ_author_name_6              'Sugihara, Y.'
_publ_author_address_2           
'Fac of Pharm Svi, Suzuka Univ of Med Sci, Suzuka, Japan'
_publ_author_address_3           
'Grad Sch of Sci and Res. Center for Materials Sci, Nagoya Univ, Nagoya, Japan'
_publ_author_address_4           'Fac of Sci, Yamaguchi Univ, Yamaguchi, Japan'



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'
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'
B B 0.0013 0.0007 '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/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'


_cell_length_a                   18.3878(11)
_cell_length_b                   7.5278(5)
_cell_length_c                   26.7776(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.221(2)
_cell_angle_gamma                90.00
_cell_volume                     3647.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6196
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      27.44

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.525469
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  'imaging plate area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25642
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         24.71
_reflns_number_total             6196
_reflns_number_gt                3362
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0859P)²+0.2021P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6196
_refine_ls_number_parameters     421
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1785
_refine_ls_wR_factor_gt          0.1425
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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

O1 O 1.72392(12) 0.0505(3) 0.95984(8) 0.0948(7) Uani 1 1 d . . .
O2 O 1.52912(12) 0.2688(3) 0.50448(7) 0.0861(7) Uani 1 1 d . . .
O3 O 1.13094(10) -0.3389(3) 0.76033(7) 0.0724(6) Uani 1 1 d . . .
N1 N 1.57337(11) -0.1688(3) 0.88108(7) 0.0541(6) Uani 1 1 d . . .
N2 N 1.57731(11) 0.2018(3) 0.64145(8) 0.0559(6) Uani 1 1 d . . .
N3 N 1.27383(10) -0.2801(3) 0.68345(7) 0.0502(5) Uani 1 1 d . . .
C1 C 1.62359(15) -0.1142(4) 0.92099(10) 0.0643(8) Uani 1 1 d . . .
H1 H 1.6224 -0.1621 0.9528 0.077 Uiso 1 1 calc R . .
C2 C 1.67631(15) 0.0098(4) 0.91606(10) 0.0650(8) Uani 1 1 d . . .
C3 C 1.67866(14) 0.0826(4) 0.86928(10) 0.0611(7) Uani 1 1 d . . .
H3 H 1.7138 0.1680 0.8655 0.073 Uiso 1 1 calc R . .
C4 C 1.62758(13) 0.0264(4) 0.82776(9) 0.0542(7) Uani 1 1 d . . .
C5 C 1.57637(13) -0.1014(4) 0.83505(9) 0.0532(7) Uani 1 1 d . . .
H5 H 1.5429 -0.1418 0.8072 0.064 Uiso 1 1 calc R . .
C6 C 1.7641(2) 0.2089(5) 0.96163(14) 0.1076(12) Uani 1 1 d . . .
H6A H 1.7989 0.2011 0.9389 0.129 Uiso 1 1 calc R . .
H6B H 1.7901 0.2282 0.9956 0.129 Uiso 1 1 calc R . .
H6C H 1.7308 0.3060 0.9517 0.129 Uiso 1 1 calc R . .
C7 C 1.62776(13) 0.1003(4) 0.77813(10) 0.0596(7) Uani 1 1 d . . .
C8 C 1.63044(14) 0.1692(4) 0.73792(10) 0.0601(7) Uani 1 1 d . . .
C9 C 1.63743(18) 0.4784(4) 0.69256(12) 0.0818(9) Uani 1 1 d . . .
H9A H 1.6795 0.5185 0.7171 0.098 Uiso 1 1 calc R . .
H9B H 1.6421 0.5299 0.6601 0.098 Uiso 1 1 calc R . .
C10 C 1.5689(2) 0.5531(5) 0.70786(17) 0.1212(14) Uani 1 1 d . . .
H10A H 1.5266 0.5213 0.6830 0.145 Uiso 1 1 calc R . .
H10B H 1.5728 0.6801 0.7101 0.145 Uiso 1 1 calc R . .
H10C H 1.5635 0.5056 0.7403 0.145 Uiso 1 1 calc R . .
C11 C 1.72128(16) 0.2012(5) 0.67322(12) 0.0800(9) Uani 1 1 d . . .
H11A H 1.7286 0.2641 0.6429 0.096 Uiso 1 1 calc R . .
H11B H 1.7608 0.2364 0.7004 0.096 Uiso 1 1 calc R . .
C12 C 1.7287(2) 0.0043(5) 0.66405(16) 0.1106(13) Uani 1 1 d . . .
H12A H 1.7192 -0.0607 0.6930 0.133 Uiso 1 1 calc R . .
H12B H 1.7779 -0.0209 0.6586 0.133 Uiso 1 1 calc R . .
H12C H 1.6938 -0.0304 0.6346 0.133 Uiso 1 1 calc R . .
C21 C 1.58030(15) 0.2618(4) 0.59408(10) 0.0644(8) Uani 1 1 d . . .
C22 C 1.52923(16) 0.2142(4) 0.55322(10) 0.0640(8) Uani 1 1 d . . .
H21 H 1.6185 0.3377 0.5895 0.077 Uiso 1 1 calc R . .
C23 C 1.47154(16) 0.1020(4) 0.55973(10) 0.0656(8) Uani 1 1 d . . .
H23 H 1.4359 0.0691 0.5321 0.079 Uiso 1 1 calc R . .
C24 C 1.46788(14) 0.0400(3) 0.60799(9) 0.0554(7) Uani 1 1 d . . .
C25 C 1.52222(14) 0.0921(3) 0.64778(9) 0.0545(7) Uani 1 1 d . . .
H25 H 1.5205 0.0496 0.6802 0.065 Uiso 1 1 calc R . .
C26 C 1.5902(2) 0.3755(5) 0.49553(13) 0.1024(12) Uani 1 1 d . . .
H26A H 1.5903 0.4860 0.5134 0.123 Uiso 1 1 calc R . .
H26B H 1.5856 0.3985 0.4598 0.123 Uiso 1 1 calc R . .
H26C H 1.6356 0.3134 0.5073 0.123 Uiso 1 1 calc R . .
C27 C 1.40768(15) -0.0723(4) 0.61628(9) 0.0595(7) Uani 1 1 d . . .
C28 C 1.35460(14) -0.1580(4) 0.62106(9) 0.0557(7) Uani 1 1 d . . .
C29 C 1.28402(17) -0.4674(4) 0.60309(11) 0.0657(8) Uani 1 1 d . . .
H29A H 1.2390(15) -0.539(4) 0.6074(10) 0.079 Uiso 1 1 d . . .
H29B H 1.2819(14) -0.467(4) 0.5658(11) 0.079 Uiso 1 1 d . . .
C30 C 1.34932(18) -0.5806(4) 0.62534(12) 0.0874(10) Uani 1 1 d . . .
H30A H 1.3940 -0.5250 0.6194 0.105 Uiso 1 1 calc R . .
H30B H 1.3446 -0.6956 0.6096 0.105 Uiso 1 1 calc R . .
H30C H 1.3510 -0.5932 0.6612 0.105 Uiso 1 1 calc R . .
C31 C 1.20998(15) -0.1566(4) 0.59260(10) 0.0718(8) Uani 1 1 d . . .
H31A H 1.1665 -0.2314 0.5898 0.086 Uiso 1 1 calc R . .
H31B H 1.2018 -0.0529 0.6124 0.086 Uiso 1 1 calc R . .
C32 C 1.21827(19) -0.0968(5) 0.53993(12) 0.1032(12) Uani 1 1 d . . .
H32A H 1.2582 -0.0133 0.5424 0.124 Uiso 1 1 calc R . .
H32B H 1.1733 -0.0412 0.5236 0.124 Uiso 1 1 calc R . .
H32C H 1.2285 -0.1977 0.5204 0.124 Uiso 1 1 calc R . .
C41 C 1.20637(13) -0.2999(3) 0.69563(9) 0.0539(7) Uani 1 1 d . . .
H41 H 1.1649 -0.2989 0.6701 0.065 Uiso 1 1 calc R . .
C42 C 1.19785(14) -0.3217(4) 0.74552(9) 0.0551(7) Uani 1 1 d . . .
C43 C 1.25923(14) -0.3258(4) 0.78325(9) 0.0565(7) Uani 1 1 d . . .
H43 H 1.2539 -0.3408 0.8169 0.068 Uiso 1 1 calc R . .
C44 C 1.32870(13) -0.3077(3) 0.77110(9) 0.0514(6) Uani 1 1 d . . .
C45 C 1.33321(13) -0.2841(3) 0.72017(9) 0.0525(7) Uani 1 1 d . . .
H45 H 1.3796 -0.2705 0.7114 0.063 Uiso 1 1 calc R . .
C46 C 1.06678(15) -0.3098(5) 0.72300(12) 0.0838(10) Uani 1 1 d . . .
H46A H 1.0694 -0.1944 0.7082 0.101 Uiso 1 1 calc R . .
H46B H 1.0237 -0.3166 0.7385 0.101 Uiso 1 1 calc R . .
H46C H 1.0639 -0.3988 0.6970 0.101 Uiso 1 1 calc R . .
C47 C 1.39444(15) -0.3109(4) 0.80935(9) 0.0569(7) Uani 1 1 d . . .
C48 C 1.44780(15) -0.3135(4) 0.84268(10) 0.0574(7) Uani 1 1 d . . .
C49 C 1.55931(15) -0.5100(4) 0.89197(11) 0.0715(8) Uani 1 1 d . . .
H49A H 1.5726 -0.5307 0.8590 0.086 Uiso 1 1 calc R . .
H49B H 1.6048 -0.4989 0.9165 0.086 Uiso 1 1 calc R . .
C50 C 1.51693(19) -0.6674(4) 0.90582(13) 0.0923(10) Uani 1 1 d . . .
H50A H 1.5112 -0.6579 0.9407 0.111 Uiso 1 1 calc R . .
H50B H 1.5434 -0.7744 0.9012 0.111 Uiso 1 1 calc R . .
H50C H 1.4691 -0.6706 0.8845 0.111 Uiso 1 1 calc R . .
C51 C 1.48133(16) -0.2814(4) 0.94081(10) 0.0737(9) Uani 1 1 d . . .
H51A H 1.4490 -0.3786 0.9463 0.088 Uiso 1 1 calc R . .
H51B H 1.5224 -0.2808 0.9691 0.088 Uiso 1 1 calc R . .
C52 C 1.4397(2) -0.1126(5) 0.94218(13) 0.1037(12) Uani 1 1 d . . .
H52A H 1.4729 -0.0139 0.9427 0.124 Uiso 1 1 calc R . .
H52B H 1.4176 -0.1101 0.9721 0.124 Uiso 1 1 calc R . .
H52C H 1.4017 -0.1049 0.9126 0.124 Uiso 1 1 calc R . .
B1 B 1.64339(17) 0.2665(5) 0.68773(12) 0.0608(8) Uani 1 1 d . . .
B2 B 1.28068(16) -0.2657(4) 0.62304(10) 0.0534(8) Uani 1 1 d . . .
B3 B 1.51350(16) -0.3231(4) 0.89020(11) 0.0581(8) Uani 1 1 d . . .


_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
O1 C2 1.368(3) . ?
O1 C6 1.399(4) . ?
O2 C22 1.368(3) . ?
O2 C26 1.436(3) . ?
O3 C42 1.364(3) . ?
O3 C46 1.421(3) . ?
N1 C1 1.347(3) . ?
N1 C5 1.343(3) . ?
N1 B3 1.648(4) . ?
N2 C21 1.357(3) . ?
N2 C25 1.341(3) . ?
N2 B1 1.648(4) . ?
N3 C41 1.346(3) . ?
N3 C45 1.334(3) . ?
N3 B2 1.648(3) . ?
C1 C2 1.369(4) . ?
C3 C2 1.375(4) . ?
C4 C3 1.388(3) . ?
C4 C7 1.441(4) . ?
C5 C4 1.384(3) . ?
C8 C7 1.204(3) . ?
C8 B1 1.585(4) . ?
C9 B1 1.605(5) . ?
C10 C9 1.502(4) . ?
C11 B1 1.625(4) . ?
C12 C11 1.512(5) . ?
C22 C21 1.358(4) . ?
C22 C23 1.391(4) . ?
C24 C23 1.387(3) . ?
C24 C27 1.441(4) . ?
C25 C24 1.382(3) . ?
C28 C27 1.195(3) . ?
C28 B2 1.592(4) . ?
C29 C30 1.506(4) . ?
C29 B2 1.615(4) . ?
C31 C32 1.514(4) . ?
C31 B2 1.629(4) . ?
C41 C42 1.382(3) . ?
C43 C42 1.375(3) . ?
C43 C44 1.380(3) . ?
C45 C44 1.392(3) . ?
C47 C44 1.439(3) . ?
C47 C48 1.204(3) . ?
C48 B3 1.593(4) . ?
C49 B3 1.636(4) . ?
C50 C49 1.500(4) . ?
C51 C52 1.487(4) . ?
C51 B3 1.603(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
_geom_angle_publ_flag
C5 N1 C1 118.6(2) . . ?
C5 N1 B3 122.7(2) . . ?
C1 N1 B3 118.7(2) . . ?
C25 N2 C21 118.7(2) . . ?
C25 N2 B1 124.0(2) . . ?
C21 N2 B1 117.3(2) . . ?
C41 N3 B2 118.7(2) . . ?
C45 N3 C41 119.2(2) . . ?
C45 N3 B2 122.01(18) . . ?
C2 O1 C6 118.3(3) . . ?
C22 O2 C26 117.3(2) . . ?
C42 O3 C46 117.36(19) . . ?
N1 C1 C2 122.0(2) . . ?
C1 C2 C3 119.8(3) . . ?
O1 C2 C1 115.3(2) . . ?
O1 C2 C3 124.9(3) . . ?
C2 C3 C4 118.8(3) . . ?
C3 C4 C7 120.6(2) . . ?
C5 C4 C3 118.7(2) . . ?
C5 C4 C7 120.8(2) . . ?
N1 C5 C4 122.1(2) . . ?
C8 C7 C4 176.4(3) . . ?
C7 C8 B1 173.4(3) . . ?
C10 C9 B1 117.8(3) . . ?
C12 C11 B1 116.4(3) . . ?
C22 C21 N2 121.9(2) . . ?
C21 C22 O2 125.0(2) . . ?
C21 C22 C23 119.5(2) . . ?
O2 C22 C23 115.5(3) . . ?
C24 C23 C22 119.0(3) . . ?
C25 C24 C23 118.3(2) . . ?
C25 C24 C27 121.2(2) . . ?
C23 C24 C27 120.4(3) . . ?
N2 C25 C24 122.4(2) . . ?
C28 C27 C24 175.6(3) . . ?
C27 C28 B2 175.3(3) . . ?
C30 C29 B2 118.4(3) . . ?
C32 C31 B2 114.4(2) . . ?
N3 C41 C42 121.0(2) . . ?
O3 C42 C43 116.7(2) . . ?
O3 C42 C41 123.7(2) . . ?
C43 C42 C41 119.6(2) . . ?
C42 C43 C44 119.9(2) . . ?
C43 C44 C45 117.5(2) . . ?
C43 C44 C47 121.8(2) . . ?
C45 C44 C47 120.7(2) . . ?
N3 C45 C44 122.8(2) . . ?
C48 C47 C44 177.6(2) . . ?
C47 C48 B3 174.7(2) . . ?
C50 C49 B3 113.5(2) . . ?
C52 C51 B3 117.2(3) . . ?
C8 B1 C9 111.6(2) . . ?
C8 B1 C11 109.5(2) . . ?
C8 B1 N2 107.4(2) . . ?
C9 B1 C11 113.3(2) . . ?
C9 B1 N2 107.6(2) . . ?
C11 B1 N2 107.1(2) . . ?
C28 B2 N3 106.3(2) . . ?
C28 B2 C29 112.7(2) . . ?
C28 B2 C31 109.7(2) . . ?
C29 B2 N3 106.1(2) . . ?
C29 B2 C31 112.5(2) . . ?
C31 B2 N3 109.3(2) . . ?
C48 B3 N1 106.3(2) . . ?
C48 B3 C49 112.1(2) . . ?
C48 B3 C51 109.0(2) . . ?
C49 B3 N1 104.8(2) . . ?
C51 B3 N1 110.1(2) . . ?
C51 B3 C49 114.2(2) . . ?



_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.71
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 999215'
