#------------------------------------------------------------------------------
#$Date: 2016-03-26 12:50:16 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180216 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/02/7110203.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_7110203
loop_
_publ_author_name
'Jillian A. Hatnean'
'Jordan W. Thomson'
'Preston A. Chase'
'Douglas W. Stephan'
_publ_section_title
;
 Imine hydrogenation by alkylaluminum catalysts
;
_journal_name_full               Chem.Commun.
_journal_page_first              301
_journal_paper_doi               10.1039/c3cc47889k
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C21 H29 Al Br N'
_chemical_formula_weight         402.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.770(5)
_cell_angle_beta                 110.985(5)
_cell_angle_gamma                111.068(5)
_cell_formula_units_Z            2
_cell_length_a                   9.5329(10)
_cell_length_b                   11.3713(13)
_cell_length_c                   11.5117(12)
_cell_measurement_temperature    150(2)
_cell_volume                     1021.5(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.985
_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  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16935
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.60
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    2.057
_exptl_absorpt_correction_T_max  0.6837
_exptl_absorpt_correction_T_min  0.6837
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.009
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0552P)²+0.8064P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1067
_reflns_number_gt                4049
_reflns_number_total             4657
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc47889k.txt
_cod_data_source_block           jh005_0m
_cod_original_cell_volume        1021.47(19)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7110203
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.13443(7) 0.47153(5) 1.07793(5) 0.01680(13) Uani 1 1 d .
Br1 Br 0.05858(4) 0.83394(3) 0.43671(3) 0.04855(12) Uani 1 1 d .
N1 N 0.1148(2) 0.59956(16) 0.97472(16) 0.0179(3) Uani 1 1 d .
C1 C 0.2719(3) 0.5692(2) 1.2715(2) 0.0248(4) Uani 1 1 d .
H1A H 0.2189 0.6217 1.2989 0.030 Uiso 1 1 calc R
H1B H 0.2632 0.5014 1.3160 0.030 Uiso 1 1 calc R
C2 C 0.4617(3) 0.6655(3) 1.3265(2) 0.0400(6) Uani 1 1 d .
H2 H 0.4727 0.7257 1.2727 0.048 Uiso 1 1 calc R
C3 C 0.5630(4) 0.5941(4) 1.3183(5) 0.1007(19) Uani 1 1 d .
H3A H 0.6823 0.6593 1.3569 0.151 Uiso 1 1 calc R
H3B H 0.5234 0.5441 1.2253 0.151 Uiso 1 1 calc R
H3C H 0.5502 0.5315 1.3673 0.151 Uiso 1 1 calc R
C4 C 0.5358(4) 0.7533(4) 1.4708(3) 0.0700(11) Uani 1 1 d .
H4A H 0.5349 0.6971 1.5265 0.105 Uiso 1 1 calc R
H4B H 0.4678 0.7989 1.4778 0.105 Uiso 1 1 calc R
H4C H 0.6522 0.8203 1.5004 0.105 Uiso 1 1 calc R
C5 C 0.1988(3) 0.3438(2) 0.9956(2) 0.0241(4) Uani 1 1 d .
H5A H 0.1435 0.3235 0.8987 0.029 Uiso 1 1 calc R
H5B H 0.3222 0.3909 1.0264 0.029 Uiso 1 1 calc R
C6 C 0.1572(3) 0.2088(2) 1.0206(2) 0.0272(4) Uani 1 1 d .
H6 H 0.0389 0.1711 1.0092 0.033 Uiso 1 1 calc R
C7 C 0.1637(4) 0.1081(3) 0.9185(3) 0.0447(7) Uani 1 1 d .
H7A H 0.2754 0.1461 0.9215 0.067 Uiso 1 1 calc R
H7B H 0.0772 0.0888 0.8298 0.067 Uiso 1 1 calc R
H7C H 0.1425 0.0250 0.9388 0.067 Uiso 1 1 calc R
C8 C 0.2723(4) 0.2257(3) 1.1605(3) 0.0438(6) Uani 1 1 d .
H8A H 0.2363 0.1389 1.1739 0.066 Uiso 1 1 calc R
H8B H 0.2659 0.2899 1.2244 0.066 Uiso 1 1 calc R
H8C H 0.3889 0.2591 1.1733 0.066 Uiso 1 1 calc R
C9 C 0.2350(2) 0.73798(19) 1.06172(19) 0.0198(4) Uani 1 1 d .
C10 C 0.2102(2) 0.7958(2) 1.1650(2) 0.0224(4) Uani 1 1 d .
H10 H 0.1134 0.7461 1.1746 0.027 Uiso 1 1 calc R
C11 C 0.3244(3) 0.9247(2) 1.2538(2) 0.0285(5) Uani 1 1 d .
H11 H 0.3059 0.9619 1.3240 0.034 Uiso 1 1 calc R
C12 C 0.4655(3) 0.9994(2) 1.2407(2) 0.0329(5) Uani 1 1 d .
H12 H 0.5435 1.0878 1.3010 0.039 Uiso 1 1 calc R
C13 C 0.4913(3) 0.9437(2) 1.1389(2) 0.0326(5) Uani 1 1 d .
H13 H 0.5879 0.9944 1.1296 0.039 Uiso 1 1 calc R
C14 C 0.3772(3) 0.8138(2) 1.0490(2) 0.0265(4) Uani 1 1 d .
H14 H 0.3966 0.7771 0.9792 0.032 Uiso 1 1 calc R
C15 C 0.1452(3) 0.5584(2) 0.8591(2) 0.0219(4) Uani 1 1 d .
H15A H 0.0661 0.4621 0.8090 0.026 Uiso 1 1 calc R
H15B H 0.2609 0.5670 0.8938 0.026 Uiso 1 1 calc R
C16 C 0.1270(2) 0.6337(2) 0.7621(2) 0.0221(4) Uani 1 1 d .
C17 C 0.1801(3) 0.6091(2) 0.6663(2) 0.0266(4) Uani 1 1 d .
H17 H 0.2310 0.5509 0.6675 0.032 Uiso 1 1 calc R
C18 C 0.1599(3) 0.6679(2) 0.5694(2) 0.0317(5) Uani 1 1 d .
H18 H 0.1955 0.6500 0.5041 0.038 Uiso 1 1 calc R
C19 C 0.0868(3) 0.7535(2) 0.5697(2) 0.0293(5) Uani 1 1 d .
C20 C 0.0351(3) 0.7812(2) 0.6640(2) 0.0292(5) Uani 1 1 d .
H20 H -0.0142 0.8406 0.6631 0.035 Uiso 1 1 calc R
C21 C 0.0561(3) 0.7212(2) 0.7604(2) 0.0253(4) Uani 1 1 d .
H21 H 0.0214 0.7404 0.8260 0.030 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'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 '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'
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
C1 Al1 C5 117.03(9) . .
C1 Al1 N1 110.92(8) . 2_567
C5 Al1 N1 115.32(8) . 2_567
C1 Al1 N1 111.79(8) . .
C5 Al1 N1 109.81(8) . .
N1 Al1 N1 88.44(7) 2_567 .
C1 Al1 Al1 120.54(7) . 2_567
C5 Al1 Al1 122.31(7) . 2_567
N1 Al1 Al1 44.57(5) 2_567 2_567
N1 Al1 Al1 43.87(5) . 2_567
C9 N1 C15 112.34(15) . .
C9 N1 Al1 121.04(12) . 2_567
C15 N1 Al1 111.73(12) . 2_567
C9 N1 Al1 109.87(12) . .
C15 N1 Al1 107.70(12) . .
Al1 N1 Al1 91.56(7) 2_567 .
C2 C1 Al1 118.91(16) . .
C2 C1 H1A 107.6 . .
Al1 C1 H1A 107.6 . .
C2 C1 H1B 107.6 . .
Al1 C1 H1B 107.6 . .
H1A C1 H1B 107.0 . .
C3 C2 C4 108.8(3) . .
C3 C2 C1 112.9(3) . .
C4 C2 C1 110.8(2) . .
C3 C2 H2 108.1 . .
C4 C2 H2 108.1 . .
C1 C2 H2 108.1 . .
C2 C3 H3A 109.5 . .
C2 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
C2 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
C2 C4 H4A 109.5 . .
C2 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C2 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C6 C5 Al1 118.53(15) . .
C6 C5 H5A 107.7 . .
Al1 C5 H5A 107.7 . .
C6 C5 H5B 107.7 . .
Al1 C5 H5B 107.7 . .
H5A C5 H5B 107.1 . .
C8 C6 C7 110.6(2) . .
C8 C6 C5 112.28(19) . .
C7 C6 C5 110.87(19) . .
C8 C6 H6 107.6 . .
C7 C6 H6 107.6 . .
C5 C6 H6 107.6 . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C6 C8 H8A 109.5 . .
C6 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C6 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C14 C9 C10 118.23(18) . .
C14 C9 N1 122.89(18) . .
C10 C9 N1 118.84(17) . .
C11 C10 C9 121.2(2) . .
C11 C10 H10 119.4 . .
C9 C10 H10 119.4 . .
C12 C11 C10 120.3(2) . .
C12 C11 H11 119.9 . .
C10 C11 H11 119.9 . .
C13 C12 C11 119.2(2) . .
C13 C12 H12 120.4 . .
C11 C12 H12 120.4 . .
C12 C13 C14 121.0(2) . .
C12 C13 H13 119.5 . .
C14 C13 H13 119.5 . .
C9 C14 C13 120.1(2) . .
C9 C14 H14 119.9 . .
C13 C14 H14 119.9 . .
N1 C15 C16 117.67(16) . .
N1 C15 H15A 107.9 . .
C16 C15 H15A 107.9 . .
N1 C15 H15B 107.9 . .
C16 C15 H15B 107.9 . .
H15A C15 H15B 107.2 . .
C21 C16 C17 118.5(2) . .
C21 C16 C15 124.12(18) . .
C17 C16 C15 117.32(19) . .
C18 C17 C16 121.2(2) . .
C18 C17 H17 119.4 . .
C16 C17 H17 119.4 . .
C17 C18 C19 118.7(2) . .
C17 C18 H18 120.6 . .
C19 C18 H18 120.6 . .
C20 C19 C18 121.4(2) . .
C20 C19 Br1 119.78(18) . .
C18 C19 Br1 118.78(17) . .
C19 C20 C21 119.1(2) . .
C19 C20 H20 120.4 . .
C21 C20 H20 120.4 . .
C16 C21 C20 120.9(2) . .
C16 C21 H21 119.5 . .
C20 C21 H21 119.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Al1 C1 1.985(2) .
Al1 C5 1.993(2) .
Al1 N1 2.0214(17) 2_567
Al1 N1 2.0469(17) .
Al1 Al1 2.9157(11) 2_567
Br1 C19 1.900(2) .
N1 C9 1.463(2) .
N1 C15 1.496(2) .
N1 Al1 2.0214(17) 2_567
C1 C2 1.547(3) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 C3 1.485(5) .
C2 C4 1.531(4) .
C2 H2 1.0000 .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 C6 1.547(3) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C8 1.521(3) .
C6 C7 1.530(3) .
C6 H6 1.0000 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C14 1.395(3) .
C9 C10 1.397(3) .
C10 C11 1.387(3) .
C10 H10 0.9500 .
C11 C12 1.387(3) .
C11 H11 0.9500 .
C12 C13 1.378(4) .
C12 H12 0.9500 .
C13 C14 1.399(3) .
C13 H13 0.9500 .
C14 H14 0.9500 .
C15 C16 1.517(3) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C21 1.389(3) .
C16 C17 1.396(3) .
C17 C18 1.386(3) .
C17 H17 0.9500 .
C18 C19 1.386(4) .
C18 H18 0.9500 .
C19 C20 1.378(3) .
C20 C21 1.390(3) .
C20 H20 0.9500 .
C21 H21 0.9500 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C1 Al1 N1 C9 11.99(15) . .
C5 Al1 N1 C9 -119.64(13) . .
N1 Al1 N1 C9 123.94(14) 2_567 .
Al1 Al1 N1 C9 123.94(14) 2_567 .
C1 Al1 N1 C15 134.64(13) . .
C5 Al1 N1 C15 3.01(14) . .
N1 Al1 N1 C15 -113.41(13) 2_567 .
Al1 Al1 N1 C15 -113.41(13) 2_567 .
C1 Al1 N1 Al1 -111.95(9) . 2_567
C5 Al1 N1 Al1 116.43(8) . 2_567
N1 Al1 N1 Al1 0.0 2_567 2_567
C5 Al1 C1 C2 62.6(2) . .
N1 Al1 C1 C2 -162.25(17) 2_567 .
N1 Al1 C1 C2 -65.3(2) . .
Al1 Al1 C1 C2 -113.55(18) 2_567 .
Al1 C1 C2 C3 -70.3(4) . .
Al1 C1 C2 C4 167.5(2) . .
C1 Al1 C5 C6 73.76(18) . .
N1 Al1 C5 C6 -59.47(18) 2_567 .
N1 Al1 C5 C6 -157.43(15) . .
Al1 Al1 C5 C6 -110.18(16) 2_567 .
Al1 C5 C6 C8 -73.4(2) . .
Al1 C5 C6 C7 162.29(18) . .
C15 N1 C9 C14 -9.8(3) . .
Al1 N1 C9 C14 -145.40(17) 2_567 .
Al1 N1 C9 C14 110.05(19) . .
C15 N1 C9 C10 172.41(17) . .
Al1 N1 C9 C10 36.8(2) 2_567 .
Al1 N1 C9 C10 -67.7(2) . .
C14 C9 C10 C11 -0.7(3) . .
N1 C9 C10 C11 177.15(19) . .
C9 C10 C11 C12 0.7(3) . .
C10 C11 C12 C13 -0.4(4) . .
C11 C12 C13 C14 0.2(4) . .
C10 C9 C14 C13 0.5(3) . .
N1 C9 C14 C13 -177.3(2) . .
C12 C13 C14 C9 -0.3(4) . .
C9 N1 C15 C16 -62.4(2) . .
Al1 N1 C15 C16 77.37(18) 2_567 .
Al1 N1 C15 C16 176.45(14) . .
N1 C15 C16 C21 -11.8(3) . .
N1 C15 C16 C17 170.51(18) . .
C21 C16 C17 C18 -1.3(3) . .
C15 C16 C17 C18 176.52(19) . .
C16 C17 C18 C19 0.6(3) . .
C17 C18 C19 C20 0.3(3) . .
C17 C18 C19 Br1 -179.86(16) . .
C18 C19 C20 C21 -0.4(3) . .
Br1 C19 C20 C21 179.78(17) . .
C17 C16 C21 C20 1.2(3) . .
C15 C16 C21 C20 -176.45(19) . .
C19 C20 C21 C16 -0.4(3) . .
