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


data_global
_journal_name_full               'Dalton Trans.'
_journal_coden_cambridge         0222
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Timothy J. Brunker'
_publ_contact_author_email       tbrunker@towson.edu
loop_
_publ_author_name
I.Novak
T.Brunker
B.Kovac
W.Polit
R.Winter
K.Kowalski
A.Rheingold

data_towson10
_database_code_depnum_ccdc_archive 'CCDC 851861'
#TrackingRef '7941_web_deposit_cif_file_0_TimothyJ.Brunker_1320173309.towson10.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H16 B Fe N'
_chemical_formula_weight         228.91

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   6.8884(4)
_cell_length_b                   10.1248(5)
_cell_length_c                   7.7647(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.8890(10)
_cell_angle_gamma                90.00
_cell_volume                     531.79(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4532
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      25.39

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             240
_exptl_absorpt_coefficient_mu    1.374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6997
_exptl_absorpt_correction_T_max  0.7707
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_reflns_number            4968
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_sigmaI/netI    0.0098
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         25.39
_reflns_number_total             1040
_reflns_number_gt                1022
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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^)+(0.0280P)^2^+0.1500P] 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         1040
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0187
_refine_ls_R_factor_gt           0.0183
_refine_ls_wR_factor_ref         0.0510
_refine_ls_wR_factor_gt          0.0508
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.145
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.004

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
Fe1 Fe 0.08310(3) 0.2500 0.31232(3) 0.02508(12) Uani 0.9751(18) 2 d SP . .
Fe1' Fe 0.5646(19) 0.2500 0.3085(16) 0.044(6) Uani 0.0249(18) 2 d SP . .
N1 N 0.2700(2) 0.2500 0.1400(2) 0.0253(3) Uani 1 2 d S . .
C1 C 0.2982(2) 0.00138(16) 0.1748(2) 0.0372(4) Uani 1 1 d . . .
C2 C 0.30338(18) 0.13743(15) 0.24673(17) 0.0308(3) Uani 1 1 d . . .
C3 C 0.35775(19) 0.18025(19) 0.42266(19) 0.0391(4) Uani 1 1 d . . .
C4 C -0.2068(3) 0.2500 0.1828(3) 0.0305(4) Uani 1 2 d S . .
C5 C -0.1678(2) 0.13643(16) 0.29018(19) 0.0335(3) Uani 1 1 d . . .
C6 C -0.1035(2) 0.17992(18) 0.4658(2) 0.0394(4) Uani 1 1 d . . .
B1 B 0.2240(3) 0.2500 -0.0694(3) 0.0289(5) Uani 1 2 d S . .
H4 H -0.246(4) 0.2500 0.067(4) 0.042(7) Uiso 1 2 d S . .
H1C H 0.176(3) -0.013(2) 0.090(2) 0.053(5) Uiso 1 1 d . . .
H1B H 0.302(3) -0.059(2) 0.267(2) 0.050(5) Uiso 1 1 d . . .
H3 H 0.377(3) 0.1247(19) 0.511(3) 0.047(5) Uiso 1 1 d . . .
H5 H -0.180(2) 0.0484(18) 0.249(2) 0.040(4) Uiso 1 1 d . . .
H1E H 0.134(3) 0.162(2) -0.114(3) 0.057(5) Uiso 1 1 d . . .
H1A H 0.410(3) -0.0117(19) 0.122(2) 0.048(5) Uiso 1 1 d . . .
H6 H -0.066(3) 0.1251(19) 0.565(2) 0.051(5) Uiso 1 1 d . . .
H1D H 0.361(4) 0.2500 -0.117(4) 0.062(8) Uiso 1 2 d S . .

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
Fe1 0.01759(16) 0.04068(19) 0.01757(16) 0.000 0.00488(10) 0.000
Fe1' 0.038(8) 0.064(10) 0.030(8) 0.000 0.007(5) 0.000
N1 0.0200(7) 0.0346(9) 0.0224(8) 0.000 0.0066(6) 0.000
C1 0.0348(8) 0.0392(8) 0.0412(8) 0.0126(7) 0.0162(7) 0.0083(6)
C2 0.0196(6) 0.0470(8) 0.0273(7) 0.0089(6) 0.0080(5) 0.0056(6)
C3 0.0206(6) 0.0717(10) 0.0245(7) 0.0101(7) 0.0033(5) 0.0060(7)
C4 0.0196(9) 0.0417(11) 0.0296(10) 0.000 0.0035(7) 0.000
C5 0.0236(6) 0.0384(8) 0.0399(8) 0.0027(6) 0.0098(6) -0.0021(6)
C6 0.0293(7) 0.0607(10) 0.0315(7) 0.0106(7) 0.0143(6) 0.0012(7)
B1 0.0339(11) 0.0338(11) 0.0194(10) 0.000 0.0064(8) 0.000

_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
Fe1 N1 2.0243(15) . ?
Fe1 C2 2.0379(13) . ?
Fe1 C2 2.0379(13) 4_565 ?
Fe1 C6 2.0384(14) . ?
Fe1 C6 2.0385(14) 4_565 ?
Fe1 C3 2.0493(14) 4_565 ?
Fe1 C3 2.0493(14) . ?
Fe1 C5 2.0559(14) . ?
Fe1 C5 2.0559(14) 4_565 ?
Fe1 C4 2.0591(19) . ?
Fe1' C3 1.947(12) . ?
Fe1' C3 1.947(12) 4_565 ?
Fe1' C4 2.003(13) 1_655 ?
Fe1' C2 2.107(11) . ?
Fe1' C2 2.107(11) 4_565 ?
Fe1' N1 2.197(13) . ?
Fe1' C5 2.200(11) 1_655 ?
Fe1' C5 2.200(11) 4_665 ?
Fe1' C6 2.483(12) 1_655 ?
Fe1' C6 2.483(12) 4_665 ?
N1 C2 1.4022(17) . ?
N1 C2 1.4023(17) 4_565 ?
N1 B1 1.597(2) . ?
C1 C2 1.484(2) . ?
C1 H1C 0.97(2) . ?
C1 H1B 0.94(2) . ?
C1 H1A 0.946(19) . ?
C2 C3 1.415(2) . ?
C3 C3 1.412(4) 4_565 ?
C3 H3 0.879(19) . ?
C4 C5 1.4159(19) 4_565 ?
C4 C5 1.4159(19) . ?
C4 Fe1' 2.003(13) 1_455 ?
C4 H4 0.89(3) . ?
C5 C6 1.422(2) . ?
C5 Fe1' 2.200(11) 1_455 ?
C5 H5 0.946(18) . ?
C6 C6 1.419(4) 4_565 ?
C6 Fe1' 2.483(12) 1_455 ?
C6 H6 0.943(19) . ?
B1 H1E 1.10(2) . ?
B1 H1D 1.08(3) . ?

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 Fe1 C2 40.38(4) . . ?
N1 Fe1 C2 40.39(4) . 4_565 ?
C2 Fe1 C2 68.01(8) . 4_565 ?
N1 Fe1 C6 159.46(5) . . ?
C2 Fe1 C6 122.21(6) . . ?
C2 Fe1 C6 157.27(6) 4_565 . ?
N1 Fe1 C6 159.46(5) . 4_565 ?
C2 Fe1 C6 157.27(6) . 4_565 ?
C2 Fe1 C6 122.21(6) 4_565 4_565 ?
C6 Fe1 C6 40.74(10) . 4_565 ?
N1 Fe1 C3 67.92(6) . 4_565 ?
C2 Fe1 C3 67.98(6) . 4_565 ?
C2 Fe1 C3 40.50(6) 4_565 4_565 ?
C6 Fe1 C3 120.65(6) . 4_565 ?
C6 Fe1 C3 105.66(6) 4_565 4_565 ?
N1 Fe1 C3 67.92(6) . . ?
C2 Fe1 C3 40.50(6) . . ?
C2 Fe1 C3 67.98(6) 4_565 . ?
C6 Fe1 C3 105.66(6) . . ?
C6 Fe1 C3 120.65(6) 4_565 . ?
C3 Fe1 C3 40.31(11) 4_565 . ?
N1 Fe1 C5 125.05(5) . . ?
C2 Fe1 C5 108.68(6) . . ?
C2 Fe1 C5 161.05(6) 4_565 . ?
C6 Fe1 C5 40.64(6) . . ?
C6 Fe1 C5 68.32(6) 4_565 . ?
C3 Fe1 C5 157.34(7) 4_565 . ?
C3 Fe1 C5 122.51(7) . . ?
N1 Fe1 C5 125.05(5) . 4_565 ?
C2 Fe1 C5 161.05(6) . 4_565 ?
C2 Fe1 C5 108.68(6) 4_565 4_565 ?
C6 Fe1 C5 68.32(6) . 4_565 ?
C6 Fe1 C5 40.64(6) 4_565 4_565 ?
C3 Fe1 C5 122.51(7) 4_565 4_565 ?
C3 Fe1 C5 157.34(7) . 4_565 ?
C5 Fe1 C5 68.01(9) . 4_565 ?
N1 Fe1 C4 110.88(7) . . ?
C2 Fe1 C4 125.25(6) . . ?
C2 Fe1 C4 125.25(6) 4_565 . ?
C6 Fe1 C4 67.98(7) . . ?
C6 Fe1 C4 67.98(7) 4_565 . ?
C3 Fe1 C4 159.67(5) 4_565 . ?
C3 Fe1 C4 159.67(5) . . ?
C5 Fe1 C4 40.25(5) . . ?
C5 Fe1 C4 40.25(5) 4_565 . ?
C3 Fe1' C3 42.5(3) . 4_565 ?
C3 Fe1' C4 158.74(15) . 1_655 ?
C3 Fe1' C4 158.74(15) 4_565 1_655 ?
C3 Fe1' C2 40.6(2) . . ?
C3 Fe1' C2 68.5(4) 4_565 . ?
C4 Fe1' C2 127.2(5) 1_655 . ?
C3 Fe1' C2 68.5(4) . 4_565 ?
C3 Fe1' C2 40.6(2) 4_565 4_565 ?
C4 Fe1' C2 127.2(5) 1_655 4_565 ?
C2 Fe1' C2 65.5(4) . 4_565 ?
C3 Fe1' N1 66.3(4) . . ?
C3 Fe1' N1 66.3(4) 4_565 . ?
C4 Fe1' N1 115.6(6) 1_655 . ?
C2 Fe1' N1 38.0(2) . . ?
C2 Fe1' N1 38.0(2) 4_565 . ?
C3 Fe1' C5 122.3(2) . 1_655 ?
C3 Fe1' C5 155.9(6) 4_565 1_655 ?
C4 Fe1' C5 39.0(2) 1_655 1_655 ?
C2 Fe1' C5 113.11(15) . 1_655 ?
C2 Fe1' C5 163.3(6) 4_565 1_655 ?
N1 Fe1' C5 130.7(4) . 1_655 ?
C3 Fe1' C5 155.9(6) . 4_665 ?
C3 Fe1' C5 122.3(2) 4_565 4_665 ?
C4 Fe1' C5 39.0(2) 1_655 4_665 ?
C2 Fe1' C5 163.3(6) . 4_665 ?
C2 Fe1' C5 113.11(15) 4_565 4_665 ?
N1 Fe1' C5 130.7(4) . 4_665 ?
C5 Fe1' C5 63.0(4) 1_655 4_665 ?
C3 Fe1' C6 110.9(4) . 1_655 ?
C3 Fe1' C6 124.4(6) 4_565 1_655 ?
C4 Fe1' C6 60.3(3) 1_655 1_655 ?
C2 Fe1' C6 128.65(19) . 1_655 ?
C2 Fe1' C6 159.0(4) 4_565 1_655 ?
N1 Fe1' C6 162.5(2) . 1_655 ?
C5 Fe1' C6 34.68(19) 1_655 1_655 ?
C5 Fe1' C6 58.4(3) 4_665 1_655 ?
C3 Fe1' C6 124.4(6) . 4_665 ?
C3 Fe1' C6 110.9(4) 4_565 4_665 ?
C4 Fe1' C6 60.3(3) 1_655 4_665 ?
C2 Fe1' C6 159.0(4) . 4_665 ?
C2 Fe1' C6 128.65(19) 4_565 4_665 ?
N1 Fe1' C6 162.5(2) . 4_665 ?
C5 Fe1' C6 58.4(3) 1_655 4_665 ?
C5 Fe1' C6 34.68(19) 4_665 4_665 ?
C6 Fe1' C6 33.20(19) 1_655 4_665 ?
C2 N1 C2 108.75(16) . 4_565 ?
C2 N1 B1 125.48(8) . . ?
C2 N1 B1 125.48(8) 4_565 . ?
C2 N1 Fe1 70.33(8) . . ?
C2 N1 Fe1 70.33(8) 4_565 . ?
B1 N1 Fe1 130.11(12) . . ?
C2 N1 Fe1' 67.56(17) . . ?
C2 N1 Fe1' 67.56(17) 4_565 . ?
B1 N1 Fe1' 126.1(3) . . ?
Fe1 N1 Fe1' 103.8(3) . . ?
C2 C1 H1C 110.2(12) . . ?
C2 C1 H1B 109.0(11) . . ?
H1C C1 H1B 108.3(16) . . ?
C2 C1 H1A 109.2(12) . . ?
H1C C1 H1A 110.7(15) . . ?
H1B C1 H1A 109.4(16) . . ?
N1 C2 C3 107.78(14) . . ?
N1 C2 C1 122.86(12) . . ?
C3 C2 C1 129.11(14) . . ?
N1 C2 Fe1 69.29(8) . . ?
C3 C2 Fe1 70.19(8) . . ?
C1 C2 Fe1 130.31(10) . . ?
N1 C2 Fe1' 74.5(3) . . ?
C3 C2 Fe1' 63.6(3) . . ?
C1 C2 Fe1' 123.1(2) . . ?
Fe1 C2 Fe1' 106.5(2) . . ?
C3 C3 C2 107.85(10) 4_565 . ?
C3 C3 Fe1' 68.74(15) 4_565 . ?
C2 C3 Fe1' 75.8(3) . . ?
C3 C3 Fe1 69.84(5) 4_565 . ?
C2 C3 Fe1 69.32(8) . . ?
Fe1' C3 Fe1 112.4(3) . . ?
C3 C3 H3 129.8(12) 4_565 . ?
C2 C3 H3 122.2(12) . . ?
Fe1' C3 H3 124.8(12) . . ?
Fe1 C3 H3 122.8(12) . . ?
C5 C4 C5 108.60(19) 4_565 . ?
C5 C4 Fe1' 78.0(2) 4_565 1_455 ?
C5 C4 Fe1' 78.0(2) . 1_455 ?
C5 C4 Fe1 69.75(9) 4_565 . ?
C5 C4 Fe1 69.75(9) . . ?
Fe1' C4 Fe1 122.8(4) 1_455 . ?
C5 C4 H4 125.69(10) 4_565 . ?
C5 C4 H4 125.69(10) . . ?
Fe1' C4 H4 112.2(17) 1_455 . ?
Fe1 C4 H4 125.0(16) . . ?
C4 C5 C6 107.66(14) . . ?
C4 C5 Fe1 70.00(9) . . ?
C6 C5 Fe1 69.02(8) . . ?
C4 C5 Fe1' 63.0(3) . 1_455 ?
C6 C5 Fe1' 83.6(3) . 1_455 ?
Fe1 C5 Fe1' 113.8(2) . 1_455 ?
C4 C5 H5 124.8(10) . . ?
C6 C5 H5 127.6(10) . . ?
Fe1 C5 H5 125.0(10) . . ?
Fe1' C5 H5 119.6(10) 1_455 . ?
C6 C6 C5 108.04(9) 4_565 . ?
C6 C6 Fe1 69.63(5) 4_565 . ?
C5 C6 Fe1 70.34(8) . . ?
C6 C6 Fe1' 73.40(9) 4_565 1_455 ?
C5 C6 Fe1' 61.7(3) . 1_455 ?
Fe1 C6 Fe1' 103.7(3) . 1_455 ?
C6 C6 H6 126.1(11) 4_565 . ?
C5 C6 H6 125.9(11) . . ?
Fe1 C6 H6 125.1(11) . . ?
Fe1' C6 H6 130.8(12) 1_455 . ?
N1 B1 H1E 108.1(10) . . ?
N1 B1 H1D 109.3(15) . . ?
H1E B1 H1D 111.8(12) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.035