# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_wut_0m
_database_code_depnum_ccdc_archive 'CCDC 2359175'
loop_
_audit_author_name
_audit_author_address
'Worawat Wattanathana'
;Department of Materials Engineering, Faculty of Engineering, Kasetsart University
Thailand
;
_audit_update_record             
;
2024-05-29 deposited with the CCDC.	2024-07-22 downloaded from the CCDC.
;
_audit_creation_date             2024-05-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H19 Al N2 O'
_chemical_formula_sum            'C16 H19 Al N2 O'
_chemical_formula_weight         282.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.2130 0.2455 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3646(6)
_cell_length_b                   9.4194(8)
_cell_length_c                   11.4053(10)
_cell_angle_alpha                77.248(2)
_cell_angle_beta                 80.825(2)
_cell_angle_gamma                82.816(2)
_cell_volume                     758.47(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.141
_cell_measurement_theta_min      4.011
_shelx_estimated_absorpt_T_max   0.848
_shelx_estimated_absorpt_T_min   0.848
_exptl_absorpt_coefficient_mu    1.139
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1522 before and 0.0335 after correction. The Ratio of minimum to maximum transmission is 0.9228. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11471
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.134
_diffrn_reflns_theta_min         4.835
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2908
_reflns_number_total             2940
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2940
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.065
_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)+(0.0361P)²+0.3880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0826
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C3(H3), C10(H10), C1(H1), C2(H2), C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C16(H16A,H16B,H16C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.72451(4) 0.33911(3) 0.25372(3) 0.01293(11) Uani 1 1 d . . . . .
O1 O 0.70847(12) 0.21183(9) 0.39460(7) 0.01775(19) Uani 1 1 d . . . . .
N1 N 0.71478(13) 0.51104(10) 0.33167(9) 0.0134(2) Uani 1 1 d . . . . .
N2 N 0.73633(13) 0.50266(11) 0.44270(9) 0.0147(2) Uani 1 1 d . . . . .
C9 C 0.75667(16) 0.37059(13) 0.52241(10) 0.0146(2) Uani 1 1 d . . . . .
C12 C 0.79760(16) 0.12707(13) 0.70582(11) 0.0171(2) Uani 1 1 d . . . . .
H12 H 0.812883 0.043414 0.768736 0.020 Uiso 1 1 calc R U . . .
C6 C 0.69839(15) 0.65875(12) 0.26383(10) 0.0139(2) Uani 1 1 d . . . . .
C14 C 0.74335(15) 0.22987(13) 0.50023(10) 0.0142(2) Uani 1 1 d . . . . .
C3 C 0.67675(17) 0.94064(13) 0.12372(12) 0.0200(3) Uani 1 1 d . . . . .
H3 H 0.669526 1.037050 0.076025 0.024 Uiso 1 1 calc R U . . .
C10 C 0.78865(16) 0.38535(13) 0.63832(11) 0.0163(2) Uani 1 1 d . . . . .
H10 H 0.796692 0.479996 0.652286 0.020 Uiso 1 1 calc R U . . .
C1 C 0.68110(16) 0.68081(13) 0.14099(11) 0.0163(2) Uani 1 1 d . . . . .
H1 H 0.676604 0.599674 0.105020 0.020 Uiso 1 1 calc R U . . .
C13 C 0.76616(16) 0.10641(13) 0.59478(11) 0.0160(2) Uani 1 1 d . . . . .
C2 C 0.67044(16) 0.82214(13) 0.07125(11) 0.0184(3) Uani 1 1 d . . . . .
H2 H 0.658822 0.837456 -0.012489 0.022 Uiso 1 1 calc R U . . .
C7 C 0.50660(17) 0.34101(13) 0.17473(11) 0.0194(3) Uani 1 1 d . . . . .
H7A H 0.472450 0.241007 0.186829 0.029 Uiso 1 1 calc R U . . .
H7B H 0.534618 0.381286 0.087670 0.029 Uiso 1 1 calc R U . . .
H7C H 0.403680 0.401685 0.210160 0.029 Uiso 1 1 calc R U . . .
C11 C 0.80823(16) 0.26582(13) 0.73077(10) 0.0165(2) Uani 1 1 d . . . . .
C4 C 0.69371(18) 0.91794(13) 0.24668(12) 0.0209(3) Uani 1 1 d . . . . .
H4 H 0.698170 0.999236 0.282457 0.025 Uiso 1 1 calc R U . . .
C8 C 0.96851(17) 0.31797(14) 0.15864(11) 0.0213(3) Uani 1 1 d . . . . .
H8A H 1.063380 0.330659 0.205776 0.032 Uiso 1 1 calc R U . . .
H8B H 0.974051 0.392241 0.083279 0.032 Uiso 1 1 calc R U . . .
H8C H 0.990311 0.220421 0.139259 0.032 Uiso 1 1 calc R U . . .
C5 C 0.70408(17) 0.77816(13) 0.31690(11) 0.0178(2) Uani 1 1 d . . . . .
H5 H 0.715020 0.763321 0.400714 0.021 Uiso 1 1 calc R U . . .
C16 C 0.75610(18) -0.04318(13) 0.57105(11) 0.0207(3) Uani 1 1 d . . . . .
H16A H 0.793056 -0.117697 0.639898 0.031 Uiso 1 1 calc R U . . .
H16B H 0.839418 -0.055509 0.497181 0.031 Uiso 1 1 calc R U . . .
H16C H 0.629262 -0.053730 0.560628 0.031 Uiso 1 1 calc R U . . .
C15 C 0.83661(17) 0.27992(14) 0.85553(11) 0.0202(3) Uani 1 1 d . . . . .
H15A H 0.720808 0.266865 0.910800 0.030 Uiso 1 1 calc R U . . .
H15B H 0.874811 0.377068 0.851526 0.030 Uiso 1 1 calc R U . . .
H15C H 0.932676 0.205001 0.885398 0.030 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O1 1.7770(9) . ?
Al1 N1 2.0012(10) . ?
Al1 C7 1.9581(12) . ?
Al1 C8 1.9568(13) . ?
O1 C14 1.3214(14) . ?
N1 N2 1.2852(14) . ?
N1 C6 1.4358(14) . ?
N2 C9 1.3762(15) . ?
C9 C14 1.4209(16) . ?
C9 C10 1.4182(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.3816(17) . ?
C12 C11 1.4114(17) . ?
C6 C1 1.3943(16) . ?
C6 C5 1.3977(17) . ?
C14 C13 1.4138(16) . ?
C3 H3 0.9500 . ?
C3 C2 1.3867(18) . ?
C3 C4 1.3945(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.3726(17) . ?
C1 H1 0.9500 . ?
C1 C2 1.3919(16) . ?
C13 C16 1.5050(16) . ?
C2 H2 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C11 C15 1.5071(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.3819(17) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C5 H5 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
O1 Al1 N1 93.45(4) . . ?
O1 Al1 C7 109.97(5) . . ?
O1 Al1 C8 111.69(5) . . ?
C7 Al1 N1 112.79(5) . . ?
C8 Al1 N1 107.98(5) . . ?
C8 Al1 C7 118.22(6) . . ?
C14 O1 Al1 127.99(7) . . ?
N2 N1 Al1 124.71(8) . . ?
N2 N1 C6 113.02(9) . . ?
C6 N1 Al1 122.07(8) . . ?
N1 N2 C9 121.98(10) . . ?
N2 C9 C14 127.04(10) . . ?
N2 C9 C10 112.94(10) . . ?
C10 C9 C14 119.99(10) . . ?
C13 C12 H12 118.2 . . ?
C13 C12 C11 123.51(11) . . ?
C11 C12 H12 118.2 . . ?
C1 C6 N1 118.00(10) . . ?
C1 C6 C5 120.13(10) . . ?
C5 C6 N1 121.84(10) . . ?
O1 C14 C9 121.85(10) . . ?
O1 C14 C13 119.45(10) . . ?
C13 C14 C9 118.69(10) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.84(11) . . ?
C4 C3 H3 120.1 . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.41(11) . . ?
C11 C10 H10 119.3 . . ?
C6 C1 H1 120.1 . . ?
C2 C1 C6 119.75(11) . . ?
C2 C1 H1 120.1 . . ?
C12 C13 C14 118.89(11) . . ?
C12 C13 C16 122.17(10) . . ?
C14 C13 C16 118.94(11) . . ?
C3 C2 C1 120.16(11) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
Al1 C7 H7A 109.5 . . ?
Al1 C7 H7B 109.5 . . ?
Al1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C12 C11 C15 120.40(11) . . ?
C10 C11 C12 117.50(11) . . ?
C10 C11 C15 122.09(11) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.54(11) . . ?
C5 C4 H4 119.7 . . ?
Al1 C8 H8A 109.5 . . ?
Al1 C8 H8B 109.5 . . ?
Al1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.58(11) . . ?
C4 C5 H5 120.2 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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 O1 C14 C9 15.95(16) . . . . ?
Al1 O1 C14 C13 -164.79(8) . . . . ?
Al1 N1 N2 C9 -4.44(15) . . . . ?
Al1 N1 C6 C1 2.73(14) . . . . ?
Al1 N1 C6 C5 -175.64(9) . . . . ?
O1 C14 C13 C12 -178.26(10) . . . . ?
O1 C14 C13 C16 1.96(16) . . . . ?
N1 Al1 O1 C14 -19.35(10) . . . . ?
N1 N2 C9 C14 -5.19(18) . . . . ?
N1 N2 C9 C10 176.77(10) . . . . ?
N1 C6 C1 C2 -178.08(10) . . . . ?
N1 C6 C5 C4 177.90(11) . . . . ?
N2 N1 C6 C1 177.75(10) . . . . ?
N2 N1 C6 C5 -0.61(16) . . . . ?
N2 C9 C14 O1 0.14(19) . . . . ?
N2 C9 C14 C13 -179.13(11) . . . . ?
N2 C9 C10 C11 178.50(10) . . . . ?
C9 C14 C13 C12 1.02(17) . . . . ?
C9 C14 C13 C16 -178.76(10) . . . . ?
C9 C10 C11 C12 0.75(17) . . . . ?
C9 C10 C11 C15 -178.14(11) . . . . ?
C6 N1 N2 C9 -179.30(10) . . . . ?
C6 C1 C2 C3 -0.08(18) . . . . ?
C14 C9 C10 C11 0.32(17) . . . . ?
C3 C4 C5 C6 0.31(19) . . . . ?
C10 C9 C14 O1 178.05(10) . . . . ?
C10 C9 C14 C13 -1.22(17) . . . . ?
C1 C6 C5 C4 -0.43(18) . . . . ?
C13 C12 C11 C10 -0.97(17) . . . . ?
C13 C12 C11 C15 177.95(11) . . . . ?
C2 C3 C4 C5 -0.08(19) . . . . ?
C7 Al1 O1 C14 -135.13(10) . . . . ?
C11 C12 C13 C14 0.07(18) . . . . ?
C11 C12 C13 C16 179.84(11) . . . . ?
C4 C3 C2 C1 -0.03(18) . . . . ?
C8 Al1 O1 C14 91.55(10) . . . . ?
C5 C6 C1 C2 0.31(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
