data_2203206
loop_
_publ_author_name
'Marilyn M. Olmstead'
'Jeff T. Suri'
'Bakthan Singaram'
_publ_section_title
;
N-[2-(Hydroxymethoxyboryl)benzyl]-4,7-phenanthrolinium bromide
methanol solvate
;
_journal_issue                 2
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o278
_journal_page_last             o280
_journal_volume                60
_journal_year                  2004
_chemical_formula_moiety       'C20 H18 B N2 O2 1+, Br 1- C H4 O'
_chemical_formula_sum          'C21 H22 B Br N2 O3'
_chemical_formula_weight       441.13
_chemical_melting_point        ?
_chemical_name_common          ?
_chemical_name_systematic
;
N-[2-(Hydroxymethoxyboryl)benzyl]-4,7-phenanthrolinium bromide
methanol solvate
;
_symmetry_cell_setting         monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 21/c'
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary   direct
_atom_sites_solution_secondary difmap
_cell_angle_alpha              90.00
_cell_angle_beta               103.723(4)
_cell_angle_gamma              90.00
_cell_formula_units_Z          4
_cell_length_a                 16.376(3)
_cell_length_b                 13.894(3)
_cell_length_c                 9.0289(15)
_cell_measurement_reflns_used  545
_cell_measurement_temperature  90(2)
_cell_measurement_theta_max    25.
_cell_measurement_theta_min    2.5
_cell_volume                   1995.7(7)
_computing_cell_refinement     SMART
_computing_data_collection     'SMART (Bruker, 2002)'
_computing_data_reduction      'SAINT (Bruker, 2002)'
_computing_molecular_graphics  'SHELXTL (Sheldrick, 1994)'
_computing_publication_material SHELXL97
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution  'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature    90(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type 'Bruker SMART 1000'
_diffrn_measurement_method     \w
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source       'normal-focus sealed tube'
_diffrn_radiation_type         MoK\a
_diffrn_radiation_wavelength   0.71073
_diffrn_reflns_av_R_equivalents 0.0612
_diffrn_reflns_av_sigmaI/netI  0.0682
_diffrn_reflns_limit_h_max     19
_diffrn_reflns_limit_h_min     -19
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_l_max     10
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_number          11491
_diffrn_reflns_theta_full      25.34
_diffrn_reflns_theta_max       25.34
_diffrn_reflns_theta_min       1.95
_diffrn_standards_decay_%      ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number       0
_exptl_absorpt_coefficient_mu  2.084
_exptl_absorpt_correction_T_max 0.9030
_exptl_absorpt_correction_T_min 0.7054
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour          colorless
_exptl_crystal_density_diffrn  1.468
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     plate
_exptl_crystal_F_000           904
_exptl_crystal_size_max        0.18
_exptl_crystal_size_mid        0.11
_exptl_crystal_size_min        0.05
_refine_diff_density_max       0.526
_refine_diff_density_min       -0.631
_refine_ls_extinction_coef     ?
_refine_ls_extinction_method   none
_refine_ls_goodness_of_fit_ref 1.119
_refine_ls_hydrogen_treatment  mixed
_refine_ls_matrix_type         full
_refine_ls_number_parameters   261
_refine_ls_number_reflns       3618
_refine_ls_number_restraints   0
_refine_ls_restrained_S_all    1.119
_refine_ls_R_factor_all        0.0677
_refine_ls_R_factor_gt         0.0420
_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/[\s^2^(Fo^2^)+(0.0382P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.0901
_refine_ls_wR_factor_ref       0.0962
_reflns_number_gt              2624
_reflns_number_total           3618
_reflns_threshold_expression   I>2\s(I)
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'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Br1 0.78239(2) 0.58393(3) 0.31425(4) 0.01940(13) Uani d . 1 . . Br
O1 0.48970(18) 0.5484(2) 0.2154(3) 0.0303(7) Uani d . 1 . . O
H1A 0.527(3) 0.585(3) 0.263(5) 0.036 Uiso d . 1 . . H
O2 0.35007(16) 0.49847(19) 0.1386(3) 0.0202(6) Uani d . 1 . . O
N1 0.16625(18) 0.5979(2) 0.3377(3) 0.0148(7) Uani d . 1 . . N
N2 -0.03533(19) 0.6233(2) -0.2513(3) 0.0177(7) Uani d . 1 . . N
C1 0.1151(2) 0.6048(2) 0.1921(4) 0.0147(8) Uani d . 1 . . C
C2 0.1491(2) 0.5906(3) 0.0625(4) 0.0163(8) Uani d . 1 . . C
H2 0.2073 0.5774 0.0754 0.020 Uiso calc R 1 . . H
C3 0.0978(2) 0.5959(3) -0.0794(4) 0.0173(8) Uani d . 1 . . C
H3 0.1206 0.5843 -0.1652 0.021 Uiso calc R 1 . . H
C4 0.0103(2) 0.6184(3) -0.1035(4) 0.0148(8) Uani d . 1 . . C
C5 -0.1165(2) 0.6429(3) -0.2732(4) 0.0185(9) Uani d . 1 . . C
H5 -0.1492 0.6469 -0.3751 0.022 Uiso calc R 1 . . H
C6 -0.1570(2) 0.6582(3) -0.1548(4) 0.0184(8) Uani d . 1 . . C
H6 -0.2155 0.6721 -0.1772 0.022 Uiso calc R 1 . . H
C7 -0.1117(2) 0.6527(3) -0.0063(4) 0.0165(8) Uani d . 1 . . C
H7 -0.1384 0.6624 0.0752 0.020 Uiso calc R 1 . . H
C8 -0.0252(2) 0.6327(3) 0.0235(4) 0.0134(8) Uani d . 1 . . C
C9 0.0285(2) 0.6249(3) 0.1754(4) 0.0126(8) Uani d . 1 . . C
C10 -0.0025(2) 0.6338(3) 0.3078(4) 0.0157(8) Uani d . 1 . . C
H10 -0.0606 0.6462 0.2983 0.019 Uiso calc R 1 . . H
C11 0.0500(2) 0.6249(3) 0.4498(4) 0.0170(8) Uani d . 1 . . C
H11 0.0288 0.6304 0.5387 0.020 Uiso calc R 1 . . H
C12 0.1347(2) 0.6077(3) 0.4614(4) 0.0179(9) Uani d . 1 . . C
H12 0.1715 0.6026 0.5597 0.021 Uiso calc R 1 . . H
C13 0.2583(2) 0.5821(3) 0.3617(4) 0.0162(8) Uani d . 1 . . C
H13A 0.2682 0.5278 0.2972 0.019 Uiso calc R 1 . . H
H13B 0.2821 0.5644 0.4695 0.019 Uiso calc R 1 . . H
C14 0.3028(2) 0.6715(3) 0.3228(4) 0.0159(8) Uani d . 1 . . C
C15 0.2760(2) 0.7617(3) 0.3585(4) 0.0203(9) Uani d . 1 . . C
H15 0.2288 0.7664 0.4022 0.024 Uiso calc R 1 . . H
C16 0.3167(2) 0.8446(3) 0.3318(4) 0.0219(9) Uani d . 1 . . C
H16 0.2970 0.9057 0.3552 0.026 Uiso calc R 1 . . H
C17 0.3865(2) 0.8383(3) 0.2708(4) 0.0250(9) Uani d . 1 . . C
H17 0.4149 0.8950 0.2518 0.030 Uiso calc R 1 . . H
C18 0.4146(2) 0.7483(3) 0.2375(4) 0.0238(9) Uani d . 1 . . C
H18 0.4635 0.7445 0.1984 0.029 Uiso calc R 1 . . H
C19 0.3733(2) 0.6624(3) 0.2598(4) 0.0169(8) Uani d . 1 . . C
B1 0.4074(3) 0.5655(3) 0.2051(5) 0.0221(10) Uani d . 1 . . B
C20 0.3772(3) 0.4130(3) 0.0738(4) 0.0272(9) Uani d . 1 . . C
H20C 0.4212 0.4298 0.0213 0.041 Uiso calc R 1 . . H
H20A 0.3294 0.3844 0.0007 0.041 Uiso calc R 1 . . H
H20B 0.3995 0.3666 0.1551 0.041 Uiso calc R 1 . . H
O3 0.60938(18) 0.6693(2) 0.3600(3) 0.0324(7) Uani d . 1 . . O
H3A 0.663(3) 0.644(3) 0.349(5) 0.039 Uiso d . 1 . . H
C21 0.6140(3) 0.6727(4) 0.5192(5) 0.0405(12) Uani d . 1 . . C
H21A 0.6155 0.6070 0.5592 0.061 Uiso calc R 1 . . H
H21B 0.5647 0.7063 0.5370 0.061 Uiso calc R 1 . . H
H21C 0.6651 0.7070 0.5710 0.061 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.0177(2) 0.0239(2) 0.01666(19) -0.00196(19) 0.00435(14) 0.00002(19)
O1 0.0200(16) 0.0284(17) 0.0426(19) 0.0021(13) 0.0077(14) -0.0105(14)
O2 0.0211(14) 0.0209(15) 0.0194(14) 0.0024(12) 0.0062(11) -0.0012(12)
N1 0.0157(15) 0.0162(18) 0.0133(15) 0.0012(13) 0.0050(12) 0.0010(13)
N2 0.0211(18) 0.0181(17) 0.0131(16) -0.0050(14) 0.0029(14) -0.0022(13)
C1 0.0172(19) 0.011(2) 0.0154(18) -0.0020(14) 0.0019(15) 0.0018(14)
C2 0.0163(18) 0.017(2) 0.0168(18) -0.0001(17) 0.0072(15) -0.0013(17)
C3 0.022(2) 0.021(2) 0.0126(17) -0.0055(17) 0.0108(15) -0.0036(16)
C4 0.018(2) 0.0120(19) 0.0146(18) -0.0009(15) 0.0039(16) 0.0033(15)
C5 0.023(2) 0.016(2) 0.0131(19) -0.0046(17) -0.0018(16) 0.0021(16)
C6 0.0153(19) 0.014(2) 0.024(2) 0.0005(16) 0.0023(16) -0.0004(17)
C7 0.0171(19) 0.019(2) 0.0146(18) -0.0007(16) 0.0051(16) -0.0018(16)
C8 0.0190(19) 0.0112(19) 0.0097(17) 0.0004(15) 0.0026(15) 0.0002(14)
C9 0.0143(18) 0.0132(19) 0.0124(18) -0.0019(15) 0.0072(15) -0.0007(14)
C10 0.0138(19) 0.018(2) 0.0164(19) 0.0025(16) 0.0047(15) 0.0003(16)
C11 0.021(2) 0.019(2) 0.0142(19) -0.0007(16) 0.0105(16) 0.0006(16)
C12 0.025(2) 0.018(2) 0.0114(18) 0.0016(16) 0.0061(16) 0.0007(15)
C13 0.0171(18) 0.018(2) 0.0149(17) 0.0022(17) 0.0063(15) 0.0005(17)
C14 0.0111(19) 0.022(2) 0.0107(18) -0.0007(15) -0.0041(15) -0.0010(16)
C15 0.020(2) 0.025(2) 0.0174(19) -0.0002(17) 0.0064(16) -0.0001(16)
C16 0.023(2) 0.019(2) 0.019(2) 0.0036(18) -0.0043(17) -0.0020(17)
C17 0.021(2) 0.023(2) 0.028(2) -0.0053(18) -0.0003(18) 0.0020(19)
C18 0.0139(19) 0.028(2) 0.030(2) 0.0010(17) 0.0049(17) 0.0014(19)
C19 0.0154(19) 0.019(2) 0.0142(19) 0.0034(16) -0.0003(15) 0.0016(16)
B1 0.026(3) 0.023(3) 0.019(2) 0.004(2) 0.009(2) 0.0048(19)
C20 0.030(2) 0.029(2) 0.023(2) 0.007(2) 0.0065(18) -0.002(2)
O3 0.0258(16) 0.040(2) 0.0306(16) 0.0043(14) 0.0056(14) -0.0022(14)
C21 0.044(3) 0.056(3) 0.024(2) 0.006(2) 0.013(2) 0.010(2)
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'
Br Br -0.2901 2.4595 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
B1 O1 H1A . . 122(3) ?
B1 O2 C20 . . 119.8(3) ?
C12 N1 C1 . . 121.1(3) ?
C12 N1 C13 . . 118.0(3) ?
C1 N1 C13 . . 120.9(3) ?
C5 N2 C4 . . 116.9(3) ?
N1 C1 C9 . . 118.7(3) ?
N1 C1 C2 . . 120.2(3) ?
C9 C1 C2 . . 121.1(3) ?
C3 C2 C1 . . 119.6(3) ?
C3 C2 H2 . . 120.2 ?
C1 C2 H2 . . 120.2 ?
C2 C3 C4 . . 121.8(3) ?
C2 C3 H3 . . 119.1 ?
C4 C3 H3 . . 119.1 ?
N2 C4 C8 . . 123.3(3) ?
N2 C4 C3 . . 117.0(3) ?
C8 C4 C3 . . 119.7(3) ?
N2 C5 C6 . . 123.8(3) ?
N2 C5 H5 . . 118.1 ?
C6 C5 H5 . . 118.1 ?
C7 C6 C5 . . 119.5(3) ?
C7 C6 H6 . . 120.2 ?
C5 C6 H6 . . 120.2 ?
C6 C7 C8 . . 119.0(3) ?
C6 C7 H7 . . 120.5 ?
C8 C7 H7 . . 120.5 ?
C7 C8 C4 . . 117.4(3) ?
C7 C8 C9 . . 123.6(3) ?
C4 C8 C9 . . 118.9(3) ?
C10 C9 C1 . . 118.6(3) ?
C10 C9 C8 . . 122.5(3) ?
C1 C9 C8 . . 118.8(3) ?
C11 C10 C9 . . 120.8(3) ?
C11 C10 H10 . . 119.6 ?
C9 C10 H10 . . 119.6 ?
C10 C11 C12 . . 118.8(3) ?
C10 C11 H11 . . 120.6 ?
C12 C11 H11 . . 120.6 ?
N1 C12 C11 . . 122.0(3) ?
N1 C12 H12 . . 119.0 ?
C11 C12 H12 . . 119.0 ?
N1 C13 C14 . . 111.7(3) ?
N1 C13 H13A . . 109.3 ?
C14 C13 H13A . . 109.3 ?
N1 C13 H13B . . 109.3 ?
C14 C13 H13B . . 109.3 ?
H13A C13 H13B . . 108.0 ?
C15 C14 C19 . . 120.6(4) ?
C15 C14 C13 . . 119.1(3) ?
C19 C14 C13 . . 120.2(3) ?
C16 C15 C14 . . 121.3(3) ?
C16 C15 H15 . . 119.4 ?
C14 C15 H15 . . 119.4 ?
C15 C16 C17 . . 119.7(4) ?
C15 C16 H16 . . 120.1 ?
C17 C16 H16 . . 120.1 ?
C16 C17 C18 . . 119.3(4) ?
C16 C17 H17 . . 120.3 ?
C18 C17 H17 . . 120.3 ?
C17 C18 C19 . . 122.4(4) ?
C17 C18 H18 . . 118.8 ?
C19 C18 H18 . . 118.8 ?
C18 C19 C14 . . 116.7(4) ?
C18 C19 B1 . . 117.3(3) ?
C14 C19 B1 . . 125.9(3) ?
O1 B1 O2 . . 119.0(4) ?
O1 B1 C19 . . 123.3(4) ?
O2 B1 C19 . . 117.6(4) ?
O2 C20 H20C . . 109.5 ?
O2 C20 H20A . . 109.5 ?
H20C C20 H20A . . 109.5 ?
O2 C20 H20B . . 109.5 ?
H20C C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C21 O3 H3A . . 106(3) ?
O3 C21 H21A . . 109.5 ?
O3 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
O3 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 B1 . 1.349(5) ?
O1 H1A . 0.83(5) ?
O2 B1 . 1.357(5) ?
O2 C20 . 1.440(5) ?
N1 C12 . 1.345(4) ?
N1 C1 . 1.384(4) ?
N1 C13 . 1.487(4) ?
N2 C5 . 1.326(5) ?
N2 C4 . 1.368(4) ?
C1 C9 . 1.418(5) ?
C1 C2 . 1.424(5) ?
C2 C3 . 1.357(5) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.433(5) ?
C3 H3 . 0.9500 ?
C4 C8 . 1.416(5) ?
C5 C6 . 1.401(5) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.372(5) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.406(5) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.447(5) ?
C9 C10 . 1.410(5) ?
C10 C11 . 1.370(5) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.386(5) ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
C13 C14 . 1.524(5) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C15 . 1.391(5) ?
C14 C19 . 1.408(5) ?
C15 C16 . 1.381(5) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.384(5) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.390(6) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.409(5) ?
C18 H18 . 0.9500 ?
C19 B1 . 1.582(6) ?
C20 H20C . 0.9800 ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
O3 C21 . 1.422(5) ?
O3 H3A . 0.98(4) ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1A O3 . 0.83(5) 1.84(5) 2.674(4) 178(5)
O3 H3A Br1 . 0.97(5) 2.22(5) 3.187(3) 177(4)
C12 H12 Br1 3_666 0.95 2.86 3.425(4) 119
C10 H10 Br1 1_455 0.95 2.75 3.604(4) 150
C13 H13A O2 . 0.99 2.22 3.017(5) 137
C11 H11 N2 1_556 0.95 2.38 3.320(5) 172
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C12 N1 C1 C9 . . . . 1.7(5) ?
C13 N1 C1 C9 . . . . -176.8(3) ?
C12 N1 C1 C2 . . . . -177.6(3) ?
C13 N1 C1 C2 . . . . 4.0(5) ?
N1 C1 C2 C3 . . . . 178.9(3) ?
C9 C1 C2 C3 . . . . -0.3(5) ?
C1 C2 C3 C4 . . . . 2.0(6) ?
C5 N2 C4 C8 . . . . 0.4(5) ?
C5 N2 C4 C3 . . . . 179.1(3) ?
C2 C3 C4 N2 . . . . 179.1(3) ?
C2 C3 C4 C8 . . . . -2.1(5) ?
C4 N2 C5 C6 . . . . -0.3(5) ?
N2 C5 C6 C7 . . . . -0.1(6) ?
C5 C6 C7 C8 . . . . 0.5(5) ?
C6 C7 C8 C4 . . . . -0.4(5) ?
C6 C7 C8 C9 . . . . -179.7(3) ?
N2 C4 C8 C7 . . . . 0.0(5) ?
C3 C4 C8 C7 . . . . -178.8(3) ?
N2 C4 C8 C9 . . . . 179.4(3) ?
C3 C4 C8 C9 . . . . 0.6(5) ?
N1 C1 C9 C10 . . . . -2.2(5) ?
C2 C1 C9 C10 . . . . 177.0(3) ?
N1 C1 C9 C8 . . . . 179.6(3) ?
C2 C1 C9 C8 . . . . -1.1(5) ?
C7 C8 C9 C10 . . . . 2.2(6) ?
C4 C8 C9 C10 . . . . -177.1(3) ?
C7 C8 C9 C1 . . . . -179.7(3) ?
C4 C8 C9 C1 . . . . 0.9(5) ?
C1 C9 C10 C11 . . . . 1.1(5) ?
C8 C9 C10 C11 . . . . 179.2(3) ?
C9 C10 C11 C12 . . . . 0.6(5) ?
C1 N1 C12 C11 . . . . 0.0(5) ?
C13 N1 C12 C11 . . . . 178.5(3) ?
C10 C11 C12 N1 . . . . -1.1(6) ?
C12 N1 C13 C14 . . . . -106.7(3) ?
C1 N1 C13 C14 . . . . 71.8(4) ?
N1 C13 C14 C15 . . . . 37.5(4) ?
N1 C13 C14 C19 . . . . -146.2(3) ?
C19 C14 C15 C16 . . . . 0.8(5) ?
C13 C14 C15 C16 . . . . 177.1(3) ?
C14 C15 C16 C17 . . . . -1.2(5) ?
C15 C16 C17 C18 . . . . -0.1(6) ?
C16 C17 C18 C19 . . . . 1.8(6) ?
C17 C18 C19 C14 . . . . -2.1(5) ?
C17 C18 C19 B1 . . . . 175.2(4) ?
C15 C14 C19 C18 . . . . 0.8(5) ?
C13 C14 C19 C18 . . . . -175.4(3) ?
C15 C14 C19 B1 . . . . -176.2(3) ?
C13 C14 C19 B1 . . . . 7.5(5) ?
C20 O2 B1 O1 . . . . -3.1(5) ?
C20 O2 B1 C19 . . . . 174.1(3) ?
C18 C19 B1 O1 . . . . 36.2(5) ?
C14 C19 B1 O1 . . . . -146.8(4) ?
C18 C19 B1 O2 . . . . -140.9(4) ?
C14 C19 B1 O2 . . . . 36.1(5) ?