# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011
data_publication_text
_journal_name_full Chem.Commun.
_journal_coden_cambridge 0182
#TrackingRef 'final.cif'
_publ_contact_author_name 'James H. Davis, Jr.'
_publ_contact_author_address
;University of South Alabama
Department of Chemistry
Chemistry Building, Room 223
Mobile AL 36688-0002
;
_publ_contact_author_phone '1 (251) 460 7427'
_publ_contact_author_fax '1 (251) 460 7359'
_publ_contact_author_email jdavis@jaguar1.usouthal.edu
_publ_section_title
;
A new building block for electroactive organic materials: Synthesis,
cyclic voltammetry, single crystal X-ray structure,
and ab initio treatment of a unique boron-based viologen
;
loop_
_publ_author_name
_publ_author_address
_publ_author_footnote
S.C.Dorman
;
Department of Chemistry
Birmingham Southern College
Birmingham AL 35254
;
;
?
;
R.A.O'Brien
;
Department of Chemistry
University of South Alabama
Mobile AL 36688-0002
;
;
?
;
A.Lewis
;
Department of Chemistry
University of South Alabama
Mobile AL 36688-0002
;
;
?
;
A.Salter
;
Department of Chemistry
University of South Alabama
Mobile AL 36688-0002
;
;
?
;
A.Wierzbicki
;
Department of Chemistry
University of South Alabama
Mobile AL 36688-0002
;
;
?
;
P.W.Hixon
;
Department of Chemistry
University of South Alabama
Mobile AL 36688-0002
;
;
?
;
R.E.Sykora
;
Department of Chemistry
University of South Alabama
Mobile AL 36688-0002
;
;
?
;
'Davis Junior, J.H.'
;
Department of Chemistry
University of South Alabama
Mobile AL 36688-0002
;
;
?
;
data_1
_database_code_depnum_ccdc_archive 'CCDC 820389'
#TrackingRef 'final.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C16 H30 B2 N4, 2(I)'
_chemical_formula_sum 'C16 H30 B2 I2 N4'
_chemical_formula_weight 553.86
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'C 2/c'
_symmetry_space_group_name_Hall '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 11.2757(17)
_cell_length_b 24.849(3)
_cell_length_c 8.7892(8)
_cell_angle_alpha 90.00
_cell_angle_beta 110.468(10)
_cell_angle_gamma 90.00
_cell_volume 2307.2(5)
_cell_formula_units_Z 4
_cell_measurement_temperature 290(2)
_cell_measurement_reflns_used 25
_cell_measurement_theta_min 7.09
_cell_measurement_theta_max 12.18
_exptl_crystal_description prism
_exptl_crystal_colour orange
_exptl_crystal_size_max 1.2
_exptl_crystal_size_mid 0.474
_exptl_crystal_size_min 0.342
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.595
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1080
_exptl_absorpt_coefficient_mu 2.731
_exptl_absorpt_correction_type psi-scan
_exptl_absorpt_correction_T_min 0.311
_exptl_absorpt_correction_T_max 0.393
_exptl_absorpt_process_details '(North et al., 1968)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 290(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Enraf-Nonius CAD-4'
_diffrn_measurement_method '\q/2\q scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time 120
_diffrn_standards_decay_% ?
_diffrn_reflns_number 4404
_diffrn_reflns_av_R_equivalents 0.0259
_diffrn_reflns_av_sigmaI/netI 0.0268
_diffrn_reflns_limit_h_min 0
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_k_min -29
_diffrn_reflns_limit_k_max 29
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_theta_min 2.09
_diffrn_reflns_theta_max 25.37
_reflns_number_total 2124
_reflns_number_gt 1735
_reflns_threshold_expression >2\s(I)
_computing_data_collection
;
CAD-4-PC Software (Enraf-Nonius, 1993)
;
_computing_cell_refinement 'CAD-4-PC Software'
_computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1996)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_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^ > 2\s(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^)+(0.0548P)^2^+1.1949P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens mixed
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.00095(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 2124
_refine_ls_number_parameters 119
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0415
_refine_ls_R_factor_gt 0.0319
_refine_ls_wR_factor_ref 0.0909
_refine_ls_wR_factor_gt 0.0860
_refine_ls_goodness_of_fit_ref 1.050
_refine_ls_restrained_S_all 1.050
_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
I1 I 0.5000 0.570762(16) 0.2500 0.06870(17) Uani 1 2 d S . .
I2 I 0.5000 0.735286(14) 0.7500 0.06233(17) Uani 1 2 d S . .
N1 N 0.1581(3) 0.64326(12) 0.7200(4) 0.0582(7) Uani 1 1 d . . .
N2 N 0.2223(3) 0.58743(12) 0.5128(4) 0.0552(7) Uani 1 1 d . . .
C2 C 0.2265(5) 0.63401(17) 0.8763(5) 0.0745(12) Uani 1 1 d . . .
H2A H 0.2492 0.5989 0.9104 0.089 Uiso 1 1 calc R . .
C3 C 0.2641(5) 0.67506(17) 0.9875(4) 0.0708(11) Uani 1 1 d . . .
H3A H 0.3128 0.6675 1.0949 0.085 Uiso 1 1 calc R . .
C4 C 0.2297(3) 0.72732(16) 0.9404(4) 0.0517(8) Uani 1 1 d . . .
C5 C 0.1590(3) 0.73580(15) 0.7793(4) 0.0573(9) Uani 1 1 d . . .
H5A H 0.1344 0.7706 0.7427 0.069 Uiso 1 1 calc R . .
C6 C 0.1244(3) 0.69366(16) 0.6720(4) 0.0584(9) Uani 1 1 d . . .
H6A H 0.0765 0.7004 0.5638 0.070 Uiso 1 1 calc R . .
C7 C 0.2275(5) 0.63428(19) 0.4087(5) 0.0750(12) Uani 1 1 d . . .
H7A H 0.2920 0.6282 0.3626 0.112 Uiso 1 1 calc R . .
H7B H 0.2468 0.6664 0.4735 0.112 Uiso 1 1 calc R . .
H7C H 0.1471 0.6384 0.3231 0.112 Uiso 1 1 calc R . .
C8 C 0.1875(5) 0.5385(2) 0.4068(6) 0.0900(15) Uani 1 1 d . . .
H8A H 0.2487 0.5331 0.3551 0.135 Uiso 1 1 calc R . .
H8B H 0.1053 0.5435 0.3256 0.135 Uiso 1 1 calc R . .
H8C H 0.1861 0.5077 0.4719 0.135 Uiso 1 1 calc R . .
C9 C 0.3524(4) 0.57862(16) 0.6312(6) 0.0715(12) Uani 1 1 d . . .
H9A H 0.4104 0.5749 0.5738 0.107 Uiso 1 1 calc R . .
H9B H 0.3538 0.5465 0.6923 0.107 Uiso 1 1 calc R . .
H9C H 0.3768 0.6088 0.7037 0.107 Uiso 1 1 calc R . .
B1 B 0.1177(5) 0.5946(2) 0.5949(6) 0.0661(11) Uani 1 1 d . . .
H1A H 0.011(4) 0.6029(18) 0.488(5) 0.081(13) Uiso 1 1 d . . .
H1B H 0.105(4) 0.5584(18) 0.661(5) 0.074(12) Uiso 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
I1 0.0684(3) 0.0626(3) 0.0816(3) 0.000 0.0344(2) 0.000
I2 0.0553(2) 0.0577(2) 0.0684(3) 0.000 0.01460(17) 0.000
N1 0.0571(18) 0.0646(19) 0.0579(17) 0.0015(14) 0.0261(14) 0.0041(14)
N2 0.0480(16) 0.0539(17) 0.0581(18) -0.0065(13) 0.0114(14) 0.0055(12)
C2 0.107(3) 0.060(2) 0.060(2) 0.0103(18) 0.033(2) 0.011(2)
C3 0.102(3) 0.064(2) 0.0470(19) 0.0093(18) 0.027(2) 0.014(2)
C4 0.0540(19) 0.059(2) 0.0502(18) 0.0081(15) 0.0289(16) 0.0087(16)
C5 0.052(2) 0.064(2) 0.0562(19) 0.0077(16) 0.0191(17) 0.0171(16)
C6 0.0500(19) 0.072(2) 0.0528(19) 0.0083(17) 0.0172(16) 0.0134(17)
C7 0.082(3) 0.083(3) 0.070(3) 0.019(2) 0.039(2) 0.025(2)
C8 0.082(3) 0.084(3) 0.097(3) -0.040(3) 0.022(3) -0.011(3)
C9 0.053(2) 0.073(3) 0.076(3) -0.0022(19) 0.006(2) 0.0164(18)
B1 0.058(3) 0.070(3) 0.074(3) -0.011(2) 0.028(2) -0.006(2)
_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
N1 C6 1.334(5) . ?
N1 C2 1.339(5) . ?
N1 B1 1.590(6) . ?
N2 C9 1.488(5) . ?
N2 C7 1.495(5) . ?
N2 C8 1.497(5) . ?
N2 B1 1.593(6) . ?
C2 C3 1.373(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.377(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.377(5) . ?
C4 C4 1.497(8) 7_567 ?
C5 C6 1.371(5) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
B1 H1A 1.26(5) . ?
B1 H1B 1.11(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
C6 N1 C2 118.9(3) . . ?
C6 N1 B1 120.9(3) . . ?
C2 N1 B1 120.1(3) . . ?
C9 N2 C7 107.6(4) . . ?
C9 N2 C8 107.2(3) . . ?
C7 N2 C8 108.0(4) . . ?
C9 N2 B1 113.9(4) . . ?
C7 N2 B1 112.6(3) . . ?
C8 N2 B1 107.4(3) . . ?
N1 C2 C3 121.7(4) . . ?
N1 C2 H2A 119.1 . . ?
C3 C2 H2A 119.1 . . ?
C2 C3 C4 120.1(4) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C5 C4 C3 117.0(4) . . ?
C5 C4 C4 122.0(4) . 7_567 ?
C3 C4 C4 121.0(4) . 7_567 ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5A 119.6 . . ?
C4 C5 H5A 119.5 . . ?
N1 C6 C5 121.2(3) . . ?
N1 C6 H6A 119.4 . . ?
C5 C6 H6A 119.4 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 B1 N2 108.7(3) . . ?
N1 B1 H1A 111(2) . . ?
N2 B1 H1A 110(2) . . ?
N1 B1 H1B 108(2) . . ?
N2 B1 H1B 113(2) . . ?
H1A B1 H1B 105(3) . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full 25.37
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.768
_refine_diff_density_min -0.763
_refine_diff_density_rms 0.096