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


data_global
_journal_name_full               Polym.Chem.
_journal_coden_cambridge         1478
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Frieder Jaekle'
_publ_contact_author_email       fjaekle@rutgers.edu
loop_
_publ_author_name
'Fei Cheng'
'Edward M. Bonder'
'Ami Doshi'
'Frieder Jaekle'

data_092908ami
_database_code_depnum_ccdc_archive 'CCDC 843756'
#TrackingRef '- XrayStructureAmi.txt'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H20 B N O'
_chemical_formula_sum            'C25 H20 B N O'
_chemical_formula_weight         361.23

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P(2)1/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                   14.0269(3)
_cell_length_b                   14.0772(3)
_cell_length_c                   9.7274(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.3180(10)
_cell_angle_gamma                90.00
_cell_volume                     1900.56(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      67.05

_exptl_crystal_description       Plate
_exptl_crystal_colour            Green-Yellow
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8259
_exptl_absorpt_correction_T_max  0.8870
_exptl_absorpt_process_details   '(SADABS; Blessing, 1995)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14033
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         67.07
_reflns_number_total             3299
_reflns_number_gt                2994
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX 2 (Bruker, 2006)'
_computing_cell_refinement       'APEX 2'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_structure_solution    'SHELXS (Sheldrick, 2004)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2004)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2004)'
_computing_publication_material  SHELXTL

_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^)+(0.0598P)^2^+0.4563P] 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         3299
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.0989
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
B1 B 0.17799(10) 0.36934(9) 0.30280(14) 0.0240(3) Uani 1 1 d . . .
C1 C 0.23796(8) 0.46718(8) 0.31729(11) 0.0238(3) Uani 1 1 d . . .
C2 C 0.22178(8) 0.53996(8) 0.21933(12) 0.0244(3) Uani 1 1 d . . .
H2 H 0.1770 0.5299 0.1376 0.029 Uiso 1 1 calc R . .
C3 C 0.26930(9) 0.62677(8) 0.23786(12) 0.0253(3) Uani 1 1 d . . .
H3 H 0.2570 0.6743 0.1683 0.030 Uiso 1 1 calc R . .
C4 C 0.33475(9) 0.64504(8) 0.35713(12) 0.0254(3) Uani 1 1 d . . .
C5 C 0.35285(9) 0.57183(9) 0.45499(12) 0.0276(3) Uani 1 1 d . . .
H5 H 0.3978 0.5817 0.5366 0.033 Uiso 1 1 calc R . .
C6 C 0.30626(9) 0.48545(9) 0.43450(12) 0.0267(3) Uani 1 1 d . . .
H6 H 0.3209 0.4368 0.5020 0.032 Uiso 1 1 calc R . .
C7 C 0.38317(9) 0.73800(9) 0.37654(13) 0.0280(3) Uani 1 1 d . . .
H7 H 0.3692 0.7825 0.3029 0.034 Uiso 1 1 calc R . .
C8 C 0.44385(10) 0.76591(10) 0.48555(14) 0.0370(3) Uani 1 1 d . . .
H8A H 0.4602 0.7242 0.5621 0.044 Uiso 1 1 calc R . .
H8B H 0.4711 0.8277 0.4875 0.044 Uiso 1 1 calc R . .
C9 C 0.24020(8) 0.27323(8) 0.31965(11) 0.0229(3) Uani 1 1 d . . .
C10 C 0.21784(8) 0.19504(8) 0.39743(12) 0.0248(3) Uani 1 1 d . . .
H10 H 0.1650 0.1992 0.4483 0.030 Uiso 1 1 calc R . .
C11 C 0.27079(9) 0.11143(8) 0.40239(12) 0.0254(3) Uani 1 1 d . . .
H11 H 0.2535 0.0598 0.4567 0.030 Uiso 1 1 calc R . .
C12 C 0.34870(8) 0.10160(8) 0.32948(12) 0.0237(3) Uani 1 1 d . . .
C13 C 0.37163(8) 0.17948(8) 0.24997(12) 0.0242(3) Uani 1 1 d . . .
H13 H 0.4238 0.1750 0.1980 0.029 Uiso 1 1 calc R . .
C14 C 0.31883(8) 0.26262(8) 0.24677(12) 0.0236(3) Uani 1 1 d . . .
H14 H 0.3365 0.3145 0.1932 0.028 Uiso 1 1 calc R . .
C15 C 0.40459(9) 0.01283(9) 0.34135(12) 0.0275(3) Uani 1 1 d . . .
H15 H 0.3805 -0.0370 0.3925 0.033 Uiso 1 1 calc R . .
C16 C 0.48432(9) -0.00559(9) 0.28914(13) 0.0327(3) Uani 1 1 d . . .
H16A H 0.5118 0.0416 0.2370 0.039 Uiso 1 1 calc R . .
H16B H 0.5143 -0.0660 0.3037 0.039 Uiso 1 1 calc R . .
C17 C 0.11041(9) 0.37472(8) 0.55214(12) 0.0258(3) Uani 1 1 d . . .
H17 H 0.1727 0.3741 0.6055 0.031 Uiso 1 1 calc R . .
C18 C 0.02819(9) 0.37868(8) 0.61885(13) 0.0278(3) Uani 1 1 d . . .
H18 H 0.0356 0.3813 0.7174 0.033 Uiso 1 1 calc R . .
C19 C -0.06286(9) 0.37887(8) 0.54430(13) 0.0279(3) Uani 1 1 d . . .
H19 H -0.1178 0.3813 0.5910 0.034 Uiso 1 1 calc R . .
C20 C -0.16067(9) 0.37532(8) 0.30187(14) 0.0303(3) Uani 1 1 d . . .
H20 H -0.2213 0.3780 0.3343 0.036 Uiso 1 1 calc R . .
C21 C -0.15592(9) 0.37120(9) 0.16152(14) 0.0314(3) Uani 1 1 d . . .
H21 H -0.2146 0.3705 0.0991 0.038 Uiso 1 1 calc R . .
C22 C -0.06850(9) 0.36802(8) 0.10537(13) 0.0282(3) Uani 1 1 d . . .
H22 H -0.0684 0.3650 0.0078 0.034 Uiso 1 1 calc R . .
C23 C 0.01636(9) 0.36940(8) 0.19585(13) 0.0239(3) Uani 1 1 d . . .
C24 C 0.01129(9) 0.37236(7) 0.33954(12) 0.0232(3) Uani 1 1 d . . .
C25 C -0.07412(9) 0.37546(8) 0.39745(13) 0.0258(3) Uani 1 1 d . . .
N1 N 0.10106(7) 0.37184(6) 0.41420(10) 0.0231(2) Uani 1 1 d . . .
O1 O 0.10697(6) 0.36737(6) 0.16862(8) 0.0256(2) 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
B1 0.0267(7) 0.0285(7) 0.0169(6) 0.0006(5) 0.0037(5) 0.0015(5)
C1 0.0260(6) 0.0262(6) 0.0201(6) -0.0002(4) 0.0063(5) 0.0048(5)
C2 0.0279(6) 0.0272(6) 0.0182(6) -0.0011(5) 0.0037(5) 0.0042(5)
C3 0.0307(6) 0.0261(6) 0.0197(6) 0.0039(4) 0.0059(5) 0.0049(5)
C4 0.0270(6) 0.0268(6) 0.0237(6) -0.0010(5) 0.0076(5) 0.0029(5)
C5 0.0295(6) 0.0315(6) 0.0212(6) 0.0005(5) 0.0010(5) 0.0006(5)
C6 0.0309(6) 0.0275(6) 0.0215(6) 0.0054(5) 0.0031(5) 0.0026(5)
C7 0.0298(6) 0.0264(6) 0.0282(6) 0.0021(5) 0.0058(5) 0.0029(5)
C8 0.0418(7) 0.0302(7) 0.0369(8) 0.0025(6) -0.0006(6) -0.0051(6)
C9 0.0252(6) 0.0262(6) 0.0160(5) -0.0020(4) -0.0012(4) -0.0020(5)
C10 0.0268(6) 0.0282(6) 0.0198(6) -0.0015(5) 0.0052(5) -0.0017(5)
C11 0.0321(6) 0.0246(6) 0.0194(6) 0.0007(5) 0.0036(5) -0.0036(5)
C12 0.0253(6) 0.0256(6) 0.0189(6) -0.0023(5) -0.0015(5) -0.0017(5)
C13 0.0233(6) 0.0286(6) 0.0207(6) -0.0020(5) 0.0036(5) -0.0017(5)
C14 0.0252(6) 0.0248(6) 0.0201(6) 0.0015(4) 0.0011(5) -0.0034(5)
C15 0.0313(6) 0.0252(6) 0.0252(6) -0.0002(5) 0.0008(5) -0.0012(5)
C16 0.0350(7) 0.0302(7) 0.0330(7) 0.0003(5) 0.0049(5) 0.0047(5)
C17 0.0334(7) 0.0236(6) 0.0200(6) 0.0004(4) 0.0024(5) 0.0021(5)
C18 0.0388(7) 0.0238(6) 0.0220(6) -0.0005(4) 0.0083(5) 0.0015(5)
C19 0.0334(7) 0.0217(6) 0.0310(7) -0.0002(5) 0.0123(5) 0.0015(5)
C20 0.0255(6) 0.0282(7) 0.0377(7) -0.0003(5) 0.0063(5) 0.0010(5)
C21 0.0281(6) 0.0304(7) 0.0336(7) 0.0001(5) -0.0025(5) 0.0017(5)
C22 0.0333(7) 0.0266(6) 0.0235(6) -0.0002(5) -0.0002(5) 0.0020(5)
C23 0.0282(6) 0.0195(6) 0.0241(6) 0.0004(4) 0.0040(5) 0.0020(5)
C24 0.0269(6) 0.0175(6) 0.0247(6) 0.0001(4) 0.0017(5) 0.0016(4)
C25 0.0306(6) 0.0174(6) 0.0301(7) -0.0003(4) 0.0065(5) 0.0013(5)
N1 0.0274(5) 0.0210(5) 0.0210(5) -0.0002(4) 0.0033(4) 0.0021(4)
O1 0.0265(4) 0.0308(5) 0.0195(4) 0.0002(3) 0.0029(3) 0.0027(3)

_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
B1 O1 1.5233(15) . ?
B1 C9 1.6054(17) . ?
B1 C1 1.6093(17) . ?
B1 N1 1.6365(16) . ?
C1 C2 1.3952(16) . ?
C1 C6 1.4028(17) . ?
C2 C3 1.3912(17) . ?
C3 C4 1.3954(17) . ?
C4 C5 1.4010(17) . ?
C4 C7 1.4738(17) . ?
C5 C6 1.3811(17) . ?
C7 C8 1.3199(19) . ?
C9 C10 1.3968(16) . ?
C9 C14 1.4028(16) . ?
C10 C11 1.3888(17) . ?
C11 C12 1.3931(17) . ?
C12 C13 1.4056(17) . ?
C12 C15 1.4708(17) . ?
C13 C14 1.3829(17) . ?
C15 C16 1.3193(18) . ?
C17 N1 1.3298(16) . ?
C17 C18 1.4037(17) . ?
C18 C19 1.3745(18) . ?
C19 C25 1.4151(19) . ?
C20 C21 1.3777(19) . ?
C20 C25 1.4184(18) . ?
C21 C22 1.4135(18) . ?
C22 C23 1.3743(17) . ?
C23 O1 1.3356(14) . ?
C23 C24 1.4104(17) . ?
C24 N1 1.3597(15) . ?
C24 C25 1.3963(17) . ?

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
O1 B1 C9 110.52(9) . . ?
O1 B1 C1 111.06(9) . . ?
C9 B1 C1 116.29(10) . . ?
O1 B1 N1 98.95(9) . . ?
C9 B1 N1 110.56(9) . . ?
C1 B1 N1 108.06(9) . . ?
C2 C1 C6 116.41(11) . . ?
C2 C1 B1 122.50(10) . . ?
C6 C1 B1 121.00(10) . . ?
C3 C2 C1 121.95(11) . . ?
C2 C3 C4 120.99(11) . . ?
C3 C4 C5 117.52(11) . . ?
C3 C4 C7 120.38(11) . . ?
C5 C4 C7 122.09(11) . . ?
C6 C5 C4 120.94(11) . . ?
C5 C6 C1 122.14(11) . . ?
C8 C7 C4 126.79(12) . . ?
C10 C9 C14 116.38(11) . . ?
C10 C9 B1 123.93(10) . . ?
C14 C9 B1 119.58(10) . . ?
C11 C10 C9 121.73(11) . . ?
C10 C11 C12 121.42(11) . . ?
C11 C12 C13 117.49(11) . . ?
C11 C12 C15 119.53(11) . . ?
C13 C12 C15 122.96(11) . . ?
C14 C13 C12 120.54(10) . . ?
C13 C14 C9 122.44(11) . . ?
C16 C15 C12 127.50(12) . . ?
N1 C17 C18 120.00(11) . . ?
C19 C18 C17 121.27(11) . . ?
C18 C19 C25 119.47(11) . . ?
C21 C20 C25 119.35(12) . . ?
C20 C21 C22 123.59(12) . . ?
C23 C22 C21 118.14(12) . . ?
O1 C23 C22 129.32(11) . . ?
O1 C23 C24 112.52(10) . . ?
C22 C23 C24 118.16(11) . . ?
N1 C24 C25 124.54(11) . . ?
N1 C24 C23 110.71(11) . . ?
C25 C24 C23 124.75(11) . . ?
C24 C25 C19 115.55(11) . . ?
C24 C25 C20 116.01(12) . . ?
C19 C25 C20 128.44(12) . . ?
C17 N1 C24 119.16(10) . . ?
C17 N1 B1 133.68(10) . . ?
C24 N1 B1 107.15(9) . . ?
C23 O1 B1 110.66(9) . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        67.07
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.038