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#$Date: 2024-03-04 08:42:19 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290063 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/53/7715370.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_7715370
loop_
_publ_author_name
'Wei, Biao'
'Wang, Chaoqun'
'Miao, Hui'
'Qin, Zhibiao'
'Huang, Mengna'
'Xu, Yan'
'Xue, Wenhui'
'Yang, Shucheng'
'Liu, Chenxu'
'Bai, Cuibing'
'Chen, Zheng'
_publ_section_title
;
 Novel bidentate N-coordinated alkylaluminum complexes: synthesis,
 characterization, and efficient catalysis for hydrophosphonylation.
;
_journal_issue                   9
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4185
_journal_page_last               4193
_journal_paper_doi               10.1039/d3dt04087a
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C23 H23 Al N2'
_chemical_formula_sum            'C23 H23 Al N2'
_chemical_formula_weight         354.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-11-14
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-12-01 deposited with the CCDC.	2024-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.965(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9561(5)
_cell_length_b                   14.6783(8)
_cell_length_c                   14.9503(8)
_cell_measurement_reflns_used    3544
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4590
_cell_measurement_theta_min      2.6610
_cell_volume                     1965.09(19)
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0950
_diffrn_reflns_av_unetI/netI     0.0934
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12566
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.566
_diffrn_reflns_theta_min         1.944
_exptl_absorpt_coefficient_mu    0.111
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4758
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0620
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1556P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1758
_refine_ls_wR_factor_ref         0.2520
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2642
_reflns_number_total             4758
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt04087a2.cif
_cod_data_source_block           exp_222
_cod_database_code               7715370
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C22(H22A,H22B)
1.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C14(H14), C18(H18), C11(H11), C2(H2), C16(H16), C10(H10), C9(H9),
 C17(H17), C5(H5), C8(H8), C3(H3), C4(H4)
1.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C23(H23A,H23B,H23C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Al1 Al 0.49774(10) 0.58112(6) 0.72721(5) 0.0553(3) Uani 1 1 d . . . . .
N2 N 0.4522(2) 0.59235(15) 0.85508(15) 0.0505(5) Uani 1 1 d . . . . .
N1 N 0.6308(2) 0.66865(14) 0.78775(13) 0.0474(5) Uani 1 1 d . . . . .
C13 C 0.7947(3) 0.77314(17) 0.70729(16) 0.0465(6) Uani 1 1 d . . . . .
C12 C 0.8641(3) 0.86326(18) 0.70241(17) 0.0481(6) Uani 1 1 d . . . . .
C1 C 0.8406(3) 0.72436(19) 0.62653(17) 0.0496(6) Uani 1 1 d . . . . .
C15 C 0.5640(3) 0.65318(17) 0.86864(16) 0.0448(6) Uani 1 1 d . . . . .
C6 C 0.9335(3) 0.7819(2) 0.57664(17) 0.0541(7) Uani 1 1 d . . . . .
C19 C 0.3695(3) 0.5654(2) 0.9255(2) 0.0588(7) Uani 1 1 d . . . . .
H19 H 0.292903 0.523406 0.916326 0.071 Uiso 1 1 calc R U . . .
C7 C 0.9476(3) 0.8686(2) 0.62297(17) 0.0520(7) Uani 1 1 d . . . . .
C14 C 0.7108(3) 0.74694(18) 0.77739(17) 0.0471(6) Uani 1 1 d . . . . .
H14 H 0.707256 0.787840 0.824810 0.056 Uiso 1 1 calc R U . . .
C18 C 0.3963(3) 0.5985(2) 1.0092(2) 0.0642(8) Uani 1 1 d . . . . .
H18 H 0.337134 0.580496 1.056544 0.077 Uiso 1 1 calc R U . . .
C11 C 0.8610(3) 0.93770(19) 0.75945(19) 0.0564(7) Uani 1 1 d . . . . .
H11 H 0.804503 0.935848 0.811028 0.068 Uiso 1 1 calc R U . . .
C2 C 0.8144(3) 0.6361(2) 0.59691(19) 0.0617(7) Uani 1 1 d . . . . .
H2 H 0.755158 0.596681 0.629678 0.074 Uiso 1 1 calc R U . . .
C16 C 0.5975(3) 0.68762(19) 0.95319(18) 0.0529(6) Uani 1 1 d . . . . .
H16 H 0.675303 0.728753 0.962040 0.063 Uiso 1 1 calc R U . . .
C10 C 0.9427(3) 1.0147(2) 0.7391(2) 0.0671(8) Uani 1 1 d . . . . .
H10 H 0.942849 1.063936 0.778251 0.081 Uiso 1 1 calc R U . . .
C9 C 1.0237(3) 1.0198(2) 0.6618(2) 0.0708(9) Uani 1 1 d . . . . .
H9 H 1.076620 1.072596 0.649045 0.085 Uiso 1 1 calc R U . . .
C17 C 0.5122(3) 0.6591(2) 1.02311(19) 0.0608(7) Uani 1 1 d . . . . .
H17 H 0.532683 0.680812 1.080472 0.073 Uiso 1 1 calc R U . . .
C5 C 0.9980(3) 0.7516(3) 0.4984(2) 0.0722(9) Uani 1 1 d . . . . .
H5 H 1.059956 0.789740 0.465986 0.087 Uiso 1 1 calc R U . . .
C8 C 1.0271(3) 0.9481(2) 0.6035(2) 0.0682(9) Uani 1 1 d . . . . .
H8 H 1.081784 0.952036 0.551317 0.082 Uiso 1 1 calc R U . . .
C3 C 0.8780(4) 0.6075(3) 0.5175(2) 0.0768(10) Uani 1 1 d . . . . .
H3 H 0.858524 0.548978 0.496553 0.092 Uiso 1 1 calc R U . . .
C20 C 0.3572(4) 0.6446(2) 0.6490(2) 0.0696(8) Uani 1 1 d . . . . .
H20A H 0.409048 0.664779 0.596113 0.084 Uiso 1 1 calc R U . . .
H20B H 0.279896 0.602228 0.629791 0.084 Uiso 1 1 calc R U . . .
C22 C 0.5750(4) 0.4586(2) 0.7071(2) 0.0745(9) Uani 1 1 d . . . . .
H22A H 0.677621 0.457258 0.728917 0.089 Uiso 1 1 calc R U . . .
H22B H 0.518776 0.416993 0.743952 0.089 Uiso 1 1 calc R U . . .
C4 C 0.9692(4) 0.6641(3) 0.4693(2) 0.0794(10) Uani 1 1 d . . . . .
H4 H 1.011557 0.643129 0.416771 0.095 Uiso 1 1 calc R U . . .
C21 C 0.2843(4) 0.7263(2) 0.6925(3) 0.0912(12) Uani 1 1 d . . . . .
H21A H 0.214108 0.753376 0.651232 0.137 Uiso 1 1 calc R U . . .
H21B H 0.359502 0.770143 0.708738 0.137 Uiso 1 1 calc R U . . .
H21C H 0.233154 0.706983 0.745182 0.137 Uiso 1 1 calc R U . . .
C23 C 0.5729(6) 0.4212(3) 0.6123(3) 0.1095(16) Uani 1 1 d . . . . .
H23A H 0.626179 0.461846 0.573946 0.164 Uiso 1 1 calc R U . . .
H23B H 0.471422 0.415746 0.591210 0.164 Uiso 1 1 calc R U . . .
H23C H 0.619650 0.362358 0.611815 0.164 Uiso 1 1 calc R U . . .
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'
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'
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
N2 Al1 C15 33.85(8) . . ?
N1 Al1 N2 68.37(9) . . ?
N1 Al1 C15 34.52(8) . . ?
C20 Al1 N2 113.71(13) . . ?
C20 Al1 N1 110.25(12) . . ?
C20 Al1 C15 117.51(12) . . ?
C20 Al1 C22 125.23(14) . . ?
C22 Al1 N2 107.87(12) . . ?
C22 Al1 N1 117.38(13) . . ?
C22 Al1 C15 116.96(12) . . ?
C15 N2 Al1 92.07(15) . . ?
C15 N2 C19 119.2(2) . . ?
C19 N2 Al1 148.6(2) . . ?
C15 N1 Al1 91.60(15) . . ?
C14 N1 Al1 144.56(17) . . ?
C14 N1 C15 118.4(2) . . ?
C12 C13 C1 105.9(2) . . ?
C14 C13 C12 122.4(2) . . ?
C14 C13 C1 131.6(3) . . ?
C7 C12 C13 108.8(2) . . ?
C11 C12 C13 132.0(2) . . ?
C11 C12 C7 119.2(2) . . ?
C6 C1 C13 108.6(2) . . ?
C2 C1 C13 132.0(3) . . ?
C2 C1 C6 119.3(3) . . ?
N2 C15 Al1 54.08(13) . . ?
N2 C15 N1 107.9(2) . . ?
N2 C15 C16 121.6(2) . . ?
N1 C15 Al1 53.88(12) . . ?
N1 C15 C16 130.4(2) . . ?
C16 C15 Al1 175.0(2) . . ?
C1 C6 C7 108.7(2) . . ?
C5 C6 C1 120.8(3) . . ?
C5 C6 C7 130.4(3) . . ?
N2 C19 H19 119.4 . . ?
N2 C19 C18 121.3(3) . . ?
C18 C19 H19 119.4 . . ?
C12 C7 C6 108.0(2) . . ?
C8 C7 C12 119.9(3) . . ?
C8 C7 C6 132.2(3) . . ?
N1 C14 H14 115.6 . . ?
C13 C14 N1 128.7(2) . . ?
C13 C14 H14 115.6 . . ?
C19 C18 H18 120.3 . . ?
C19 C18 C17 119.4(3) . . ?
C17 C18 H18 120.3 . . ?
C12 C11 H11 120.2 . . ?
C10 C11 C12 119.5(3) . . ?
C10 C11 H11 120.2 . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C15 C16 H16 121.0 . . ?
C17 C16 C15 117.9(3) . . ?
C17 C16 H16 121.0 . . ?
C11 C10 H10 119.4 . . ?
C9 C10 C11 121.1(3) . . ?
C9 C10 H10 119.4 . . ?
C10 C9 H9 119.6 . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 H9 119.6 . . ?
C18 C17 H17 119.7 . . ?
C16 C17 C18 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C6 C5 H5 120.5 . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 H5 120.5 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.5(3) . . ?
C9 C8 H8 120.2 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
Al1 C20 H20A 108.9 . . ?
Al1 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C21 C20 Al1 113.6(2) . . ?
C21 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
Al1 C22 H22A 107.7 . . ?
Al1 C22 H22B 107.7 . . ?
H22A C22 H22B 107.1 . . ?
C23 C22 Al1 118.5(3) . . ?
C23 C22 H22A 107.7 . . ?
C23 C22 H22B 107.7 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
Al1 N2 1.968(2) . ?
Al1 N1 1.963(2) . ?
Al1 C15 2.429(3) . ?
Al1 C20 1.942(3) . ?
Al1 C22 1.952(3) . ?
N2 C15 1.354(3) . ?
N2 C19 1.357(3) . ?
N1 C15 1.377(3) . ?
N1 C14 1.364(3) . ?
C13 C12 1.464(4) . ?
C13 C1 1.468(3) . ?
C13 C14 1.356(3) . ?
C12 C7 1.416(3) . ?
C12 C11 1.387(4) . ?
C1 C6 1.408(4) . ?
C1 C2 1.388(4) . ?
C15 C16 1.389(4) . ?
C6 C7 1.453(4) . ?
C6 C5 1.387(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.360(4) . ?
C7 C8 1.400(4) . ?
C14 H14 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.381(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.383(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.370(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.377(4) . ?
C9 H9 0.9300 . ?
C9 C8 1.367(5) . ?
C17 H17 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.379(5) . ?
C8 H8 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.377(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.518(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.520(5) . ?
C4 H4 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Al1 N2 C15 N1 1.52(19) . . . . ?
Al1 N2 C15 C16 -177.1(2) . . . . ?
Al1 N2 C19 C18 176.5(3) . . . . ?
Al1 N1 C15 N2 -1.52(19) . . . . ?
Al1 N1 C15 C16 176.9(3) . . . . ?
Al1 N1 C14 C13 -41.1(4) . . . . ?
N2 C15 C16 C17 -0.9(4) . . . . ?
N2 C19 C18 C17 -1.5(4) . . . . ?
N1 C15 C16 C17 -179.1(3) . . . . ?
C13 C12 C7 C6 -0.4(3) . . . . ?
C13 C12 C7 C8 -179.0(2) . . . . ?
C13 C12 C11 C10 177.9(3) . . . . ?
C13 C1 C6 C7 -0.8(3) . . . . ?
C13 C1 C6 C5 177.4(2) . . . . ?
C13 C1 C2 C3 -177.7(3) . . . . ?
C12 C13 C1 C6 0.5(3) . . . . ?
C12 C13 C1 C2 177.1(3) . . . . ?
C12 C13 C14 N1 174.5(2) . . . . ?
C12 C7 C8 C9 0.3(4) . . . . ?
C12 C11 C10 C9 1.9(4) . . . . ?
C1 C13 C12 C7 0.0(3) . . . . ?
C1 C13 C12 C11 -179.7(3) . . . . ?
C1 C13 C14 N1 -7.8(4) . . . . ?
C1 C6 C7 C12 0.8(3) . . . . ?
C1 C6 C7 C8 179.1(3) . . . . ?
C1 C6 C5 C4 0.5(4) . . . . ?
C1 C2 C3 C4 1.7(5) . . . . ?
C15 N2 C19 C18 0.2(4) . . . . ?
C15 N1 C14 C13 174.4(2) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
C6 C1 C2 C3 -1.4(4) . . . . ?
C6 C7 C8 C9 -177.9(3) . . . . ?
C6 C5 C4 C3 -0.3(5) . . . . ?
C19 N2 C15 Al1 178.1(3) . . . . ?
C19 N2 C15 N1 179.6(2) . . . . ?
C19 N2 C15 C16 1.0(4) . . . . ?
C19 C18 C17 C16 1.6(4) . . . . ?
C7 C12 C11 C10 -1.8(4) . . . . ?
C7 C6 C5 C4 178.3(3) . . . . ?
C14 N1 C15 Al1 160.3(2) . . . . ?
C14 N1 C15 N2 158.8(2) . . . . ?
C14 N1 C15 C16 -22.8(4) . . . . ?
C14 C13 C12 C7 178.2(2) . . . . ?
C14 C13 C12 C11 -1.5(4) . . . . ?
C14 C13 C1 C6 -177.5(3) . . . . ?
C14 C13 C1 C2 -0.9(5) . . . . ?
C11 C12 C7 C6 179.3(2) . . . . ?
C11 C12 C7 C8 0.7(4) . . . . ?
C11 C10 C9 C8 -0.9(5) . . . . ?
C2 C1 C6 C7 -177.9(2) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C10 C9 C8 C7 -0.2(5) . . . . ?
C5 C6 C7 C12 -177.2(3) . . . . ?
C5 C6 C7 C8 1.1(5) . . . . ?
