# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2009

data_global

_journal_coden_Cambridge         222

loop_
_publ_author_name
'Marcus Cole'
'Sean G Alexander'
'Samantha K. Furfari'
'Marc Kloth'

_publ_contact_author_name        'Marcus Cole'
_publ_contact_author_email       M.COLE@UNSW.EDU.AU

_publ_section_title              
;
Hydride-Bromide Exchange at an NHC - A New Route to
Brominated Alanes and Gallanes
;

# Attachment 'Cpd 5.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 711718'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            '[AlBr2H(IMes)]'
_chemical_melting_point          '545 dec.'
_chemical_formula_moiety         'C21 H25 Al Br2 N2'
_chemical_formula_sum            'C21 H25 Al Br2 N2'
_chemical_formula_weight         492.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Al Al 0.0645 0.0514 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_int_tables_number      61

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

_cell_length_a                   14.1065(2)
_cell_length_b                   16.5232(3)
_cell_length_c                   19.4059(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4523.21(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1984
_exptl_absorpt_coefficient_mu    3.630
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5305
_exptl_absorpt_correction_T_max  0.7129
_exptl_absorpt_process_details   'performed as part of the DENZO-SMN package'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  g'graphite'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'psi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            46827
_diffrn_reflns_av_R_equivalents  0.1178
_diffrn_reflns_av_sigmaI/netI    0.0821
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         29.57
_reflns_number_total             6173
_reflns_number_gt                3642
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius Collect'
_computing_cell_refinement       DENZO-SMN
_computing_data_reduction        X-Seed
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed / POV-Ray'
_computing_publication_material  'Microsoft Office 2000'

_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^)+(0.0670P)^2^+2.8169P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6173
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1403
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
Br1 Br 0.66088(3) 0.24073(3) 0.34835(2) 0.02863(14) Uani 1 1 d . . .
Br2 Br 0.62795(3) 0.38144(3) 0.50003(2) 0.03285(14) Uani 1 1 d . . .
Al1 Al 0.71999(8) 0.35305(7) 0.40541(6) 0.0198(3) Uani 1 1 d . . .
N1 N 0.9320(2) 0.35242(19) 0.41056(15) 0.0170(7) Uani 1 1 d . . .
N2 N 0.8817(2) 0.28620(19) 0.49790(15) 0.0165(7) Uani 1 1 d . . .
C1 C 0.8514(3) 0.3252(2) 0.44046(19) 0.0170(8) Uani 1 1 d . . .
C2 C 1.0107(3) 0.3312(2) 0.44774(19) 0.0223(9) Uani 1 1 d . . .
H2 H 1.0748 0.3433 0.4367 0.027 Uiso 1 1 calc R . .
C3 C 0.9792(3) 0.2896(2) 0.5032(2) 0.0231(9) Uani 1 1 d . . .
H3 H 1.0169 0.2671 0.5389 0.028 Uiso 1 1 calc R . .
C4 C 0.9373(3) 0.3950(2) 0.34479(18) 0.0193(8) Uani 1 1 d . . .
C5 C 0.9342(3) 0.4795(2) 0.3457(2) 0.0222(9) Uani 1 1 d . . .
C6 C 0.9437(3) 0.5184(2) 0.2826(2) 0.0239(9) Uani 1 1 d . . .
H6 H 0.9424 0.5758 0.2814 0.029 Uiso 1 1 calc R . .
C7 C 0.9549(3) 0.4762(3) 0.2214(2) 0.0264(9) Uani 1 1 d . . .
C8 C 0.9560(3) 0.3921(3) 0.2236(2) 0.0248(9) Uani 1 1 d . . .
H8 H 0.9626 0.3628 0.1817 0.030 Uiso 1 1 calc R . .
C9 C 0.9477(3) 0.3496(2) 0.28487(19) 0.0209(8) Uani 1 1 d . . .
C10 C 0.9218(4) 0.5259(3) 0.4118(2) 0.0345(11) Uani 1 1 d . . .
H10A H 0.9145 0.5836 0.4015 0.052 Uiso 1 1 calc R . .
H10B H 0.9777 0.5180 0.4410 0.052 Uiso 1 1 calc R . .
H10C H 0.8653 0.5062 0.4359 0.052 Uiso 1 1 calc R . .
C11 C 0.9668(4) 0.5207(3) 0.1539(2) 0.0410(12) Uani 1 1 d . . .
H11A H 0.9818 0.4818 0.1173 0.061 Uiso 1 1 calc R . .
H11B H 1.0185 0.5600 0.1581 0.061 Uiso 1 1 calc R . .
H11C H 0.9079 0.5490 0.1425 0.061 Uiso 1 1 calc R . .
C12 C 0.9502(3) 0.2589(2) 0.2865(2) 0.0299(10) Uani 1 1 d . . .
H12A H 0.9620 0.2382 0.2399 0.045 Uiso 1 1 calc R . .
H12B H 0.8893 0.2383 0.3032 0.045 Uiso 1 1 calc R . .
H12C H 1.0010 0.2409 0.3173 0.045 Uiso 1 1 calc R . .
C13 C 0.8268(3) 0.2357(2) 0.5442(2) 0.0185(8) Uani 1 1 d . . .
C14 C 0.8116(3) 0.1555(2) 0.52523(19) 0.0189(8) Uani 1 1 d . . .
C15 C 0.7665(3) 0.1050(2) 0.57242(19) 0.0207(9) Uani 1 1 d . . .
H15 H 0.7553 0.0501 0.5603 0.025 Uiso 1 1 calc R . .
C16 C 0.7374(3) 0.1325(2) 0.63681(19) 0.0211(9) Uani 1 1 d . . .
C17 C 0.7532(3) 0.2137(2) 0.65310(19) 0.0218(9) Uani 1 1 d . . .
H17 H 0.7321 0.2336 0.6964 0.026 Uiso 1 1 calc R . .
C18 C 0.7988(3) 0.2662(2) 0.6080(2) 0.0227(9) Uani 1 1 d . . .
C19 C 0.8469(3) 0.1221(2) 0.4571(2) 0.0250(9) Uani 1 1 d . . .
H19A H 0.8133 0.1487 0.4191 0.038 Uiso 1 1 calc R . .
H19B H 0.8352 0.0637 0.4553 0.038 Uiso 1 1 calc R . .
H19C H 0.9151 0.1324 0.4528 0.038 Uiso 1 1 calc R . .
C20 C 0.6938(3) 0.0759(3) 0.6883(2) 0.0308(10) Uani 1 1 d . . .
H20A H 0.6527 0.0372 0.6644 0.046 Uiso 1 1 calc R . .
H20B H 0.6561 0.1070 0.7215 0.046 Uiso 1 1 calc R . .
H20C H 0.7440 0.0466 0.7127 0.046 Uiso 1 1 calc R . .
C21 C 0.8193(3) 0.3522(3) 0.6282(2) 0.0315(10) Uani 1 1 d . . .
H21A H 0.8879 0.3594 0.6333 0.047 Uiso 1 1 calc R . .
H21B H 0.7879 0.3643 0.6720 0.047 Uiso 1 1 calc R . .
H21C H 0.7956 0.3888 0.5924 0.047 Uiso 1 1 calc R . .
H1 H 0.716(2) 0.4594(19) 0.3493(14) 0.000(8) 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
Br1 0.0280(2) 0.0328(2) 0.0251(2) -0.00404(18) -0.00067(19) -0.00572(19)
Br2 0.0306(3) 0.0340(3) 0.0340(3) -0.00740(19) 0.00966(19) -0.00120(19)
Al1 0.0179(6) 0.0208(6) 0.0207(6) 0.0027(5) 0.0008(5) -0.0005(5)
N1 0.0174(16) 0.0180(16) 0.0155(16) 0.0018(13) 0.0020(13) -0.0013(13)
N2 0.0176(16) 0.0182(16) 0.0137(16) 0.0047(12) 0.0014(13) -0.0003(13)
C1 0.019(2) 0.0140(18) 0.018(2) -0.0006(15) -0.0008(16) -0.0004(15)
C2 0.019(2) 0.024(2) 0.023(2) 0.0034(17) -0.0021(17) -0.0012(16)
C3 0.019(2) 0.025(2) 0.025(2) 0.0031(18) -0.0050(18) 0.0024(17)
C4 0.0152(19) 0.028(2) 0.0146(19) 0.0059(16) 0.0024(15) 0.0005(16)
C5 0.024(2) 0.019(2) 0.023(2) 0.0031(16) -0.0033(17) -0.0043(16)
C6 0.026(2) 0.019(2) 0.027(2) 0.0058(17) -0.0005(18) -0.0024(17)
C7 0.021(2) 0.036(3) 0.022(2) 0.0087(18) -0.0035(17) -0.0033(18)
C8 0.020(2) 0.034(2) 0.020(2) 0.0000(17) 0.0019(17) -0.0016(18)
C9 0.018(2) 0.024(2) 0.020(2) 0.0004(17) 0.0021(16) -0.0001(16)
C10 0.050(3) 0.024(2) 0.029(2) 0.0004(19) -0.001(2) 0.001(2)
C11 0.048(3) 0.047(3) 0.028(2) 0.015(2) 0.000(2) -0.004(2)
C12 0.038(3) 0.026(2) 0.025(2) -0.0018(18) 0.008(2) 0.0030(19)
C13 0.017(2) 0.021(2) 0.017(2) 0.0049(15) 0.0009(16) 0.0014(16)
C14 0.0166(19) 0.020(2) 0.020(2) 0.0007(16) -0.0008(16) 0.0032(16)
C15 0.016(2) 0.021(2) 0.025(2) 0.0034(17) -0.0012(16) 0.0009(16)
C16 0.0146(19) 0.030(2) 0.018(2) 0.0062(16) -0.0010(16) 0.0046(16)
C17 0.023(2) 0.028(2) 0.015(2) 0.0006(17) 0.0027(17) 0.0032(17)
C18 0.026(2) 0.021(2) 0.022(2) 0.0006(17) -0.0021(17) 0.0049(17)
C19 0.030(2) 0.022(2) 0.023(2) -0.0025(16) 0.0006(18) 0.0002(18)
C20 0.026(2) 0.032(3) 0.034(3) 0.010(2) 0.007(2) 0.0021(19)
C21 0.047(3) 0.028(2) 0.020(2) -0.0029(18) 0.004(2) -0.002(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
Br1 Al1 2.3164(13) . ?
Br2 Al1 2.2973(13) . ?
Al1 C1 2.028(4) . ?
Al1 H1 2.07(3) . ?
N1 C1 1.353(5) . ?
N1 C2 1.370(5) . ?
N1 C4 1.459(5) . ?
N2 C1 1.357(5) . ?
N2 C3 1.380(5) . ?
N2 C13 1.450(5) . ?
C2 C3 1.351(5) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C9 1.391(5) . ?
C4 C5 1.397(5) . ?
C5 C6 1.389(5) . ?
C5 C10 1.504(6) . ?
C6 C7 1.386(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(6) . ?
C7 C11 1.511(6) . ?
C8 C9 1.386(5) . ?
C8 H8 0.9500 . ?
C9 C12 1.500(6) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.393(5) . ?
C13 C18 1.393(5) . ?
C14 C15 1.393(5) . ?
C14 C19 1.517(5) . ?
C15 C16 1.392(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.396(6) . ?
C16 C20 1.500(6) . ?
C17 C18 1.391(6) . ?
C17 H17 0.9500 . ?
C18 C21 1.501(6) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C1 Al1 Br2 107.15(12) . . ?
C1 Al1 Br1 107.93(12) . . ?
Br2 Al1 Br1 110.01(5) . . ?
C1 Al1 H1 113.2(9) . . ?
Br2 Al1 H1 103.5(8) . . ?
Br1 Al1 H1 114.8(8) . . ?
C1 N1 C2 111.7(3) . . ?
C1 N1 C4 125.3(3) . . ?
C2 N1 C4 122.8(3) . . ?
C1 N2 C3 110.8(3) . . ?
C1 N2 C13 127.9(3) . . ?
C3 N2 C13 120.7(3) . . ?
N1 C1 N2 104.2(3) . . ?
N1 C1 Al1 123.3(3) . . ?
N2 C1 Al1 132.2(3) . . ?
C3 C2 N1 106.4(3) . . ?
C3 C2 H2 126.8 . . ?
N1 C2 H2 126.8 . . ?
C2 C3 N2 106.8(3) . . ?
C2 C3 H3 126.6 . . ?
N2 C3 H3 126.6 . . ?
C9 C4 C5 123.5(3) . . ?
C9 C4 N1 118.5(3) . . ?
C5 C4 N1 118.0(3) . . ?
C6 C5 C4 116.6(4) . . ?
C6 C5 C10 121.8(4) . . ?
C4 C5 C10 121.5(3) . . ?
C7 C6 C5 122.3(4) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C6 C7 C8 118.5(4) . . ?
C6 C7 C11 120.8(4) . . ?
C8 C7 C11 120.7(4) . . ?
C9 C8 C7 122.1(4) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 C4 117.0(4) . . ?
C8 C9 C12 121.4(4) . . ?
C4 C9 C12 121.6(3) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 122.4(4) . . ?
C14 C13 N2 117.7(3) . . ?
C18 C13 N2 119.6(3) . . ?
C13 C14 C15 117.8(4) . . ?
C13 C14 C19 121.7(3) . . ?
C15 C14 C19 120.3(4) . . ?
C16 C15 C14 122.0(4) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C17 118.0(4) . . ?
C15 C16 C20 121.1(4) . . ?
C17 C16 C20 120.9(4) . . ?
C18 C17 C16 122.1(4) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C17 C18 C13 117.7(4) . . ?
C17 C18 C21 121.1(4) . . ?
C13 C18 C21 121.3(4) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        29.57
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         2.959
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.126
_chemical_compound_source        toluene

#===END