#------------------------------------------------------------------------------
#$Date: 2018-08-11 21:05:56 +0300 (Sat, 11 Aug 2018) $
#$Revision: 209586 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/10/7001008.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7001008
loop_
_publ_author_name
'Alexander, Sean G.'
'Cole, Marcus L.'
'Furfari, Samantha K.'
'Kloth, Marc'
_publ_section_title
;
 Hydride--bromide exchange at an NHC---a new route to brominated alanes
 and gallanes
;
_journal_coden_ASTM              DTARAF
_journal_issue                   16
_journal_name_full               'Dalton Transactions'
_journal_page_first              2909
_journal_page_last               2911
_journal_paper_doi               10.1039/b821367d
_journal_year                    2009
_chemical_compound_source        toluene
_chemical_formula_moiety         'C21 H25 Al Br2 N2'
_chemical_formula_sum            'C21 H25 Al Br2 N2'
_chemical_formula_weight         492.23
_chemical_name_common            '[AlBr2H(IMes)]'
_chemical_temperature_decomposition 545
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.1065(2)
_cell_length_b                   16.5232(3)
_cell_length_c                   19.4059(3)
_cell_measurement_temperature    123(2)
_cell_volume                     4523.21(13)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       'Nonius Collect'
_computing_data_reduction        X-Seed
_computing_molecular_graphics    'X-Seed / POV-Ray'
_computing_publication_material  'Microsoft Office 2000'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'psi and omega scans'
_diffrn_radiation_monochromator  g'graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1178
_diffrn_reflns_av_sigmaI/netI    0.0821
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            46827
_diffrn_reflns_theta_full        29.57
_diffrn_reflns_theta_max         29.57
_diffrn_reflns_theta_min         2.10
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.630
_exptl_absorpt_correction_T_max  0.7129
_exptl_absorpt_correction_T_min  0.5305
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'performed as part of the DENZO-SMN package'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         2.959
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         6173
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0537
_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/[σ²(Fo²)+(0.0670P)²+2.8169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1403
_reflns_number_gt                3642
_reflns_number_total             6173
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B821367D.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_temperature_decomposition' since the value had been '545
dec.'. The value '545 dec.' was changed to '545'.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               7001008
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'
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_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'
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 . . ?
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 . ?
