#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/78/4077859.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_4077859
loop_
_publ_author_name
'Koller, Jürgen'
'Bergman, Robert G.'
_publ_section_title
;
 Controlled Hydrosilylation of Carbonyls and Imines Catalyzed by a
 Cationic Aluminum Alkyl Complex
;
_journal_issue                   7
_journal_name_full               Organometallics
_journal_page_first              2530
_journal_paper_doi               10.1021/om2008277
_journal_volume                  31
_journal_year                    2012
_chemical_formula_sum            'C10.5 H19 Al0.5 B0.5 N3 O0.5'
_chemical_formula_weight         214.18
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2011-04-13 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.476(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.328(3)
_cell_length_b                   13.462(3)
_cell_length_c                   11.636(2)
_cell_measurement_reflns_used    5183
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.36
_cell_measurement_theta_min      2.46
_cell_volume                     2476.5(8)
_computing_cell_refinement       'Bruker APEX2 v.2009.1'
_computing_data_collection       'Bruker APEX2 v.2009.1'
_computing_data_reduction        'Bruker APEX2 v.2009.1'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  'Bruker SHELXTL v6.14'
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10986
_diffrn_reflns_theta_full        25.42
_diffrn_reflns_theta_max         25.42
_diffrn_reflns_theta_min         1.81
_diffrn_standards_decay_%        1
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9927
_exptl_absorpt_correction_T_min  0.9702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2389
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0488
_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)+(0.0634P)²+3.0419P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1381
_reflns_number_gt                1951
_reflns_number_total             2389
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2008277_si_002.cif
_cod_data_source_block           jk-ii-173
_cod_original_cell_volume        2476.5(9)
_cod_original_sg_symbol_H-M      C2/m
_cod_original_formula_sum        'C10.50 H19 Al0.50 B0.50 N3 O0.50'
_cod_database_code               4077859
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
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
Al1 Al 0.24188(6) 0.0000 0.65637(8) 0.0326(3) Uani 1 2 d S
O1 O 0.0000 0.2818(2) 0.0000 0.0586(7) Uani 1 2 d S
N1 N 0.18443(10) 0.10657(12) 0.55977(14) 0.0303(4) Uani 1 1 d .
N2 N 0.12332(10) 0.09454(12) 0.45532(14) 0.0308(4) Uani 1 1 d .
N3 N 0.26807(15) 0.0000 0.3727(2) 0.0311(5) Uani 1 2 d S
N4 N 0.18472(14) 0.0000 0.3096(2) 0.0303(5) Uani 1 2 d S
B1 B 0.1154(2) 0.0000 0.3776(3) 0.0313(7) Uani 1 2 d S
H1 H 0.0556(18) 0.0000 0.319(3) 0.028(7) Uiso 1 2 d S
C1 C 0.24304(16) 0.24128(16) 0.7004(2) 0.0444(6) Uani 1 1 d .
H1A H 0.2953 0.2021 0.7187 0.067 Uiso 1 1 calc R
H1B H 0.2157 0.2359 0.7661 0.067 Uiso 1 1 calc R
H1C H 0.2564 0.3110 0.6893 0.067 Uiso 1 1 calc R
C2 C 0.18496(13) 0.20294(15) 0.58978(19) 0.0346(5) Uani 1 1 d .
C3 C 0.12522(15) 0.25299(16) 0.5050(2) 0.0413(5) Uani 1 1 d .
H3A H 0.1126 0.3219 0.5042 0.050 Uiso 1 1 calc R
C4 C 0.08746(14) 0.18369(16) 0.42167(19) 0.0371(5) Uani 1 1 d .
C5 C 0.01971(16) 0.1982(2) 0.3104(2) 0.0526(7) Uani 1 1 d .
H5A H -0.0264 0.1512 0.3086 0.079 Uiso 1 1 calc R
H5B H 0.0430 0.1867 0.2417 0.079 Uiso 1 1 calc R
H5C H -0.0020 0.2663 0.3078 0.079 Uiso 1 1 calc R
C6 C 0.4072(2) 0.0000 0.3285(3) 0.0488(8) Uani 1 2 d S
H6A H 0.4261 0.0000 0.4153 0.073 Uiso 0.50 2 calc SPR
H6B H 0.4288 0.0594 0.2972 0.073 Uiso 0.25 1 calc PR
H6C H 0.4288 -0.0594 0.2972 0.073 Uiso 0.25 1 calc PR
H6D H 0.4297 0.0000 0.2578 0.073 Uiso 0.50 2 calc SPR
H6E H 0.4270 -0.0594 0.3759 0.073 Uiso 0.25 1 calc PR
H6F H 0.4270 0.0594 0.3759 0.073 Uiso 0.25 1 calc PR
C7 C 0.31250(19) 0.0000 0.2913(3) 0.0345(7) Uani 1 2 d S
C8 C 0.2598(2) 0.0000 0.1773(3) 0.0396(7) Uani 1 2 d S
H8A H 0.2763 0.0000 0.1046 0.047 Uiso 1 2 calc SR
C9 C 0.1791(2) 0.0000 0.1914(3) 0.0365(7) Uani 1 2 d S
C10 C 0.0974(2) 0.0000 0.0992(3) 0.0531(9) Uani 1 2 d S
H10A H 0.0505 0.0000 0.1377 0.080 Uiso 0.50 2 calc SPR
H10B H 0.0940 -0.0594 0.0496 0.080 Uiso 0.25 1 calc PR
H10C H 0.0940 0.0594 0.0496 0.080 Uiso 0.25 1 calc PR
H10D H 0.1085 0.0000 0.0203 0.080 Uiso 0.50 2 calc SPR
H10E H 0.0650 0.0594 0.1083 0.080 Uiso 0.25 1 calc PR
H10F H 0.0650 -0.0594 0.1083 0.080 Uiso 0.25 1 calc PR
C11 C 0.36464(19) 0.0000 0.6788(3) 0.0410(7) Uani 1 2 d S
H11A H 0.3892 -0.0564 0.7289 0.062 Uiso 0.25 1 calc PR
H11B H 0.3882 0.0621 0.7172 0.062 Uiso 0.25 1 calc PR
H11C H 0.3780 -0.0057 0.6015 0.062 Uiso 0.25 1 calc PR
H11D H 0.3811 0.0564 0.6362 0.062 Uiso 0.25 1 calc PR
H11E H 0.3821 -0.0621 0.6479 0.062 Uiso 0.25 1 calc PR
H11F H 0.3923 0.0057 0.7636 0.062 Uiso 0.25 1 calc PR
C12 C 0.20218(19) 0.0000 0.8047(2) 0.0292(6) Uani 1 2 d S
H12A H 0.2302 -0.0537 0.8568 0.044 Uiso 0.25 1 calc PR
H12B H 0.1408 -0.0102 0.7850 0.044 Uiso 0.25 1 calc PR
H12C H 0.2159 0.0639 0.8453 0.044 Uiso 0.25 1 calc PR
H12D H 0.1611 0.0537 0.8013 0.044 Uiso 0.25 1 calc PR
H12E H 0.2505 0.0102 0.8730 0.044 Uiso 0.25 1 calc PR
H12F H 0.1754 -0.0639 0.8127 0.044 Uiso 0.25 1 calc PR
C13 C -0.06878(19) 0.3403(2) 0.0140(3) 0.0705(8) Uani 1 1 d .
H13A H -0.0885 0.3841 -0.0558 0.085 Uiso 1 1 calc R
H13B H -0.0509 0.3825 0.0855 0.085 Uiso 1 1 calc R
C14 C -0.13815(18) 0.2731(3) 0.0261(3) 0.0783(10) Uani 1 1 d .
H14A H -0.1865 0.3127 0.0352 0.117 Uiso 1 1 calc R
H14B H -0.1184 0.2307 0.0961 0.117 Uiso 1 1 calc R
H14C H -0.1553 0.2314 -0.0449 0.117 Uiso 1 1 calc R
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'
Al Al 0.0645 0.0514 '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
N1 Al1 N1 96.91(10) . 6
N1 Al1 C11 114.41(8) . .
N1 Al1 C11 114.41(8) 6 .
N1 Al1 C12 106.91(8) . .
N1 Al1 C12 106.91(8) 6 .
C11 Al1 C12 115.44(14) . .
C13 O1 C13 112.3(3) . 2
C2 N1 N2 107.43(16) . .
C2 N1 Al1 126.87(14) . .
N2 N1 Al1 124.79(12) . .
C4 N2 N1 108.54(16) . .
C4 N2 B1 126.49(18) . .
N1 N2 B1 123.31(17) . .
C7 N3 N4 105.3(2) . .
C9 N4 N3 110.4(2) . .
C9 N4 B1 130.7(2) . .
N3 N4 B1 118.9(2) . .
N4 B1 N2 109.66(16) . 6
N4 B1 N2 109.66(16) . .
N2 B1 N2 110.6(2) 6 .
N4 B1 H1 110.5(15) . .
N2 B1 H1 108.2(8) 6 .
N2 B1 H1 108.2(8) . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
N1 C2 C3 109.20(19) . .
N1 C2 C1 121.44(19) . .
C3 C2 C1 129.4(2) . .
C4 C3 C2 106.59(19) . .
C4 C3 H3A 126.7 . .
C2 C3 H3A 126.7 . .
N2 C4 C3 108.24(19) . .
N2 C4 C5 122.8(2) . .
C3 C4 C5 128.9(2) . .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C4 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C7 C6 H6A 109.5 . .
C7 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C7 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C7 C6 H6D 109.5 . .
H6A C6 H6D 141.1 . .
H6B C6 H6D 56.3 . .
H6C C6 H6D 56.3 . .
C7 C6 H6E 109.5 . .
H6A C6 H6E 56.3 . .
H6B C6 H6E 141.1 . .
H6C C6 H6E 56.3 . .
H6D C6 H6E 109.5 . .
C7 C6 H6F 109.5 . .
H6A C6 H6F 56.3 . .
H6B C6 H6F 56.3 . .
H6C C6 H6F 141.1 . .
H6D C6 H6F 109.5 . .
H6E C6 H6F 109.5 . .
N3 C7 C8 111.2(3) . .
N3 C7 C6 120.2(3) . .
C8 C7 C6 128.6(3) . .
C9 C8 C7 105.7(3) . .
C9 C8 H8A 127.1 . .
C7 C8 H8A 127.1 . .
N4 C9 C8 107.4(3) . .
N4 C9 C10 123.5(3) . .
C8 C9 C10 129.1(3) . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C9 C10 H10D 109.5 . .
H10A C10 H10D 141.1 . .
H10B C10 H10D 56.3 . .
H10C C10 H10D 56.3 . .
C9 C10 H10E 109.5 . .
H10A C10 H10E 56.3 . .
H10B C10 H10E 141.1 . .
H10C C10 H10E 56.3 . .
H10D C10 H10E 109.5 . .
C9 C10 H10F 109.5 . .
H10A C10 H10F 56.3 . .
H10B C10 H10F 56.3 . .
H10C C10 H10F 141.1 . .
H10D C10 H10F 109.5 . .
H10E C10 H10F 109.5 . .
Al1 C11 H11A 109.5 . .
Al1 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
Al1 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
Al1 C11 H11D 109.5 . .
H11A C11 H11D 141.1 . .
H11B C11 H11D 56.3 . .
H11C C11 H11D 56.3 . .
Al1 C11 H11E 109.5 . .
H11A C11 H11E 56.3 . .
H11B C11 H11E 141.1 . .
H11C C11 H11E 56.3 . .
H11D C11 H11E 109.5 . .
Al1 C11 H11F 109.5 . .
H11A C11 H11F 56.3 . .
H11B C11 H11F 56.3 . .
H11C C11 H11F 141.1 . .
H11D C11 H11F 109.5 . .
H11E C11 H11F 109.5 . .
Al1 C12 H12A 109.5 . .
Al1 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
Al1 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
Al1 C12 H12D 109.5 . .
H12A C12 H12D 141.1 . .
H12B C12 H12D 56.3 . .
H12C C12 H12D 56.3 . .
Al1 C12 H12E 109.5 . .
H12A C12 H12E 56.3 . .
H12B C12 H12E 141.1 . .
H12C C12 H12E 56.3 . .
H12D C12 H12E 109.5 . .
Al1 C12 H12F 109.5 . .
H12A C12 H12F 56.3 . .
H12B C12 H12F 56.3 . .
H12C C12 H12F 141.1 . .
H12D C12 H12F 109.5 . .
H12E C12 H12F 109.5 . .
O1 C13 C14 108.6(3) . .
O1 C13 H13A 110.0 . .
C14 C13 H13A 110.0 . .
O1 C13 H13B 110.0 . .
C14 C13 H13B 110.0 . .
H13A C13 H13B 108.4 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Al1 N1 1.9169(17) .
Al1 N1 1.9169(17) 6
Al1 C11 1.956(3) .
Al1 C12 1.989(3) .
O1 C13 1.414(3) .
O1 C13 1.414(3) 2
N1 C2 1.343(3) .
N1 N2 1.376(2) .
N2 C4 1.350(3) .
N2 B1 1.548(2) .
N3 C7 1.329(4) .
N3 N4 1.375(3) .
N4 C9 1.356(4) .
N4 B1 1.535(4) .
B1 N2 1.548(2) 6
B1 H1 1.04(3) .
C1 C2 1.488(3) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 C3 1.378(3) .
C3 C4 1.375(3) .
C3 H3A 0.9500 .
C4 C5 1.491(3) .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 C7 1.499(4) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C6 H6D 0.9800 .
C6 H6E 0.9800 .
C6 H6F 0.9800 .
C7 C8 1.389(4) .
C8 C9 1.367(4) .
C8 H8A 0.9500 .
C9 C10 1.488(4) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C10 H10D 0.9800 .
C10 H10E 0.9800 .
C10 H10F 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C11 H11D 0.9800 .
C11 H11E 0.9800 .
C11 H11F 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C12 H12D 0.9800 .
C12 H12E 0.9800 .
C12 H12F 0.9800 .
C13 C14 1.484(4) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
