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#$Date: 2019-11-26 16:02:58 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243616 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/93/4089351.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_4089351
loop_
_publ_author_name
'Vela, Javier'
'Zhu, Liwei'
'Flaschenriem, Christine J.'
'Brennessel, William W.'
'Lachicotte, Rene J.'
'Holland, Patrick L.'
_publ_section_title
;
 Macrocyclic Binucleating β-Diketiminate Ligands and their Lithium,
 Aluminum, and Zinc Complexes.
;
_journal_issue                   14
_journal_name_full               Organometallics
_journal_page_first              3416
_journal_page_last               3423
_journal_paper_doi               10.1021/om0700258
_journal_volume                  26
_journal_year                    2007
_chemical_formula_moiety         'C30 H42 Al2 N4'
_chemical_formula_sum            'C30 H42 Al2 N4'
_chemical_formula_weight         512.64
_chemical_name_common            holjv62
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 107.887(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.0065(4)
_cell_length_b                   15.1913(7)
_cell_length_c                   10.9765(5)
_cell_measurement_reflns_used    4978
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      29.23
_cell_measurement_theta_min      2.37
_cell_volume                     1429.22(11)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD Platform'
_diffrn_measurement_method       'area detector, ω scans per φ'
_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  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21892
_diffrn_reflns_theta_full        30.49
_diffrn_reflns_theta_max         30.49
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_correction_T_min  0.9812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Blessing, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         4271
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0378
_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)+(0.0550P)²+0.3624P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                3319
_reflns_number_total             4271
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om0700258-file003.cif
_cod_data_source_block           mBinAl2Me4solvent
_cod_database_code               4089351
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Al1 Al 0.03829(4) 0.18209(2) 0.07683(3) 0.01480(10) Uani 1 1 d .
C13 C -0.16854(15) 0.12703(9) 0.04569(13) 0.0271(3) Uani 1 1 d .
H13A H -0.1641 0.0656 0.0198 0.041 Uiso 1 1 calc R
H13B H -0.2458 0.1590 -0.0225 0.041 Uiso 1 1 calc R
H13C H -0.1984 0.1291 0.1243 0.041 Uiso 1 1 calc R
C14 C 0.04292(14) 0.30709(8) 0.12675(12) 0.0191(2) Uani 1 1 d .
H14A H 0.0940 0.3127 0.2191 0.029 Uiso 1 1 calc R
H14B H -0.0640 0.3296 0.1053 0.029 Uiso 1 1 calc R
H14C H 0.1011 0.3411 0.0806 0.029 Uiso 1 1 calc R
N11 N 0.19905(11) 0.11874(6) 0.19845(9) 0.01543(19) Uani 1 1 d .
N21 N 0.12029(12) 0.16760(6) -0.06229(9) 0.0156(2) Uani 1 1 d .
C11 C 0.45783(15) 0.05010(8) 0.28786(12) 0.0220(3) Uani 1 1 d .
H11A H 0.4857 0.0894 0.3622 0.033 Uiso 1 1 calc R
H11B H 0.5499 0.0395 0.2603 0.033 Uiso 1 1 calc R
H11C H 0.4199 -0.0059 0.3111 0.033 Uiso 1 1 calc R
C21 C 0.33164(13) 0.09221(7) 0.18016(11) 0.0167(2) Uani 1 1 d .
C31 C 0.36219(13) 0.10208(7) 0.06336(11) 0.0179(2) Uani 1 1 d .
H31 H 0.4618 0.0829 0.0613 0.021 Uiso 1 1 calc R
C41 C 0.26271(14) 0.13700(7) -0.05111(11) 0.0170(2) Uani 1 1 d .
C51 C 0.32543(16) 0.14043(9) -0.16312(13) 0.0251(3) Uani 1 1 d .
H51A H 0.2598 0.1044 -0.2331 0.038 Uiso 1 1 calc R
H51B H 0.4324 0.1177 -0.1372 0.038 Uiso 1 1 calc R
H51C H 0.3250 0.2015 -0.1921 0.038 Uiso 1 1 calc R
C12 C 0.17693(15) 0.10557(8) 0.32455(11) 0.0185(2) Uani 1 1 d .
H12A H 0.0890 0.1430 0.3296 0.022 Uiso 1 1 calc R
H12B H 0.2718 0.1263 0.3912 0.022 Uiso 1 1 calc R
C22 C 0.14448(13) 0.01142(7) 0.35548(11) 0.0159(2) Uani 1 1 d .
C32 C 0.07616(14) -0.04944(8) 0.25920(11) 0.0169(2) Uani 1 1 d .
H32 H 0.0534 -0.0328 0.1719 0.020 Uiso 1 1 calc R
C42 C 0.04108(13) -0.13434(7) 0.28989(11) 0.0161(2) Uani 1 1 d .
C52 C 0.07326(14) -0.15815(8) 0.41804(11) 0.0173(2) Uani 1 1 d .
H52 H 0.0471 -0.2154 0.4397 0.021 Uiso 1 1 calc R
C62 C 0.14340(14) -0.09833(8) 0.51397(11) 0.0186(2) Uani 1 1 d .
H62 H 0.1667 -0.1151 0.6012 0.022 Uiso 1 1 calc R
C72 C 0.17969(14) -0.01408(8) 0.48302(11) 0.0178(2) Uani 1 1 d .
H72 H 0.2288 0.0263 0.5492 0.021 Uiso 1 1 calc R
C82 C 0.02451(15) 0.20275(8) -0.18656(11) 0.0188(2) Uani 1 1 d .
H82A H 0.0887 0.2447 -0.2178 0.023 Uiso 1 1 calc R
H82B H -0.0635 0.2362 -0.1732 0.023 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'
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'
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
N11 Al1 N21 96.05(4) . .
N11 Al1 C14 110.21(5) . .
N21 Al1 C14 110.73(5) . .
N11 Al1 C13 112.44(5) . .
N21 Al1 C13 112.98(5) . .
C14 Al1 C13 113.22(6) . .
Al1 C13 H13A 109.5 . .
Al1 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
Al1 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
Al1 C14 H14A 109.5 . .
Al1 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
Al1 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C21 N11 C12 119.15(10) . .
C21 N11 Al1 124.85(8) . .
C12 N11 Al1 115.80(8) . .
C41 N21 C82 119.00(10) . .
C41 N21 Al1 124.46(8) . .
C82 N21 Al1 116.13(8) . .
C21 C11 H11A 109.5 . .
C21 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C21 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
N11 C21 C31 122.89(10) . .
N11 C21 C11 120.31(11) . .
C31 C21 C11 116.79(11) . .
C21 C31 C41 127.54(11) . .
C21 C31 H31 116.2 . .
C41 C31 H31 116.2 . .
N21 C41 C31 123.04(11) . .
N21 C41 C51 120.32(11) . .
C31 C41 C51 116.62(11) . .
C41 C51 H51A 109.5 . .
C41 C51 H51B 109.5 . .
H51A C51 H51B 109.5 . .
C41 C51 H51C 109.5 . .
H51A C51 H51C 109.5 . .
H51B C51 H51C 109.5 . .
N11 C12 C22 115.42(9) . .
N11 C12 H12A 108.4 . .
C22 C12 H12A 108.4 . .
N11 C12 H12B 108.4 . .
C22 C12 H12B 108.4 . .
H12A C12 H12B 107.5 . .
C72 C22 C32 119.21(11) . .
C72 C22 C12 119.13(10) . .
C32 C22 C12 121.63(10) . .
C42 C32 C22 120.64(10) . .
C42 C32 H32 119.7 . .
C22 C32 H32 119.7 . .
C52 C42 C32 119.45(10) . .
C52 C42 C82 119.27(10) . 3
C32 C42 C82 121.21(10) . 3
C62 C52 C42 120.07(11) . .
C62 C52 H52 120.0 . .
C42 C52 H52 120.0 . .
C52 C62 C72 120.29(11) . .
C52 C62 H62 119.9 . .
C72 C62 H62 119.9 . .
C62 C72 C22 120.30(11) . .
C62 C72 H72 119.8 . .
C22 C72 H72 119.8 . .
N21 C82 C42 115.27(9) . 3
N21 C82 H82A 108.5 . .
C42 C82 H82A 108.5 3 .
N21 C82 H82B 108.5 . .
C42 C82 H82B 108.5 3 .
H82A C82 H82B 107.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Al1 N11 1.9019(10) .
Al1 N21 1.9023(10) .
Al1 C14 1.9734(12) .
Al1 C13 1.9736(13) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
N11 C21 1.3327(15) .
N11 C12 1.4714(14) .
N21 C41 1.3341(15) .
N21 C82 1.4721(15) .
C11 C21 1.5077(16) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C21 C31 1.3995(17) .
C31 C41 1.4041(16) .
C31 H31 0.9500 .
C41 C51 1.5034(17) .
C51 H51A 0.9800 .
C51 H51B 0.9800 .
C51 H51C 0.9800 .
C12 C22 1.5190(16) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C22 C72 1.3920(15) .
C22 C32 1.3967(16) .
C32 C42 1.3937(16) .
C32 H32 0.9500 .
C42 C52 1.3939(16) .
C42 C82 1.5178(16) 3
C52 C62 1.3875(17) .
C52 H52 0.9500 .
C62 C72 1.3886(17) .
C62 H62 0.9500 .
C72 H72 0.9500 .
C82 C42 1.5178(16) 3
C82 H82A 0.9900 .
C82 H82B 0.9900 .
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
N21 Al1 N11 C21 10.28(10) . .
C14 Al1 N11 C21 -104.44(10) . .
C13 Al1 N11 C21 128.22(10) . .
N21 Al1 N11 C12 -174.86(8) . .
C14 Al1 N11 C12 70.41(9) . .
C13 Al1 N11 C12 -56.92(9) . .
N11 Al1 N21 C41 -11.43(10) . .
C14 Al1 N21 C41 102.87(10) . .
C13 Al1 N21 C41 -128.94(10) . .
N11 Al1 N21 C82 176.00(8) . .
C14 Al1 N21 C82 -69.70(9) . .
C13 Al1 N21 C82 58.49(9) . .
C12 N11 C21 C31 179.92(10) . .
Al1 N11 C21 C31 -5.38(16) . .
C12 N11 C21 C11 -0.62(16) . .
Al1 N11 C21 C11 174.07(8) . .
N11 C21 C31 C41 -2.24(18) . .
C11 C21 C31 C41 178.29(11) . .
C82 N21 C41 C31 -179.84(10) . .
Al1 N21 C41 C31 7.78(16) . .
C82 N21 C41 C51 1.41(16) . .
Al1 N21 C41 C51 -170.97(9) . .
C21 C31 C41 N21 0.92(19) . .
C21 C31 C41 C51 179.72(11) . .
C21 N11 C12 C22 -74.00(13) . .
Al1 N11 C12 C22 110.84(10) . .
N11 C12 C22 C72 155.89(11) . .
N11 C12 C22 C32 -25.97(16) . .
C72 C22 C32 C42 1.03(17) . .
C12 C22 C32 C42 -177.12(11) . .
C22 C32 C42 C52 0.66(18) . .
C22 C32 C42 C82 -176.44(11) . 3
C32 C42 C52 C62 -1.68(18) . .
C82 C42 C52 C62 175.47(11) 3 .
C42 C52 C62 C72 1.01(18) . .
C52 C62 C72 C22 0.70(18) . .
C32 C22 C72 C62 -1.71(18) . .
C12 C22 C72 C62 176.48(11) . .
C41 N21 C82 C42 72.78(14) . 3
Al1 N21 C82 C42 -114.22(10) . 3
