# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1879149'
loop_
_audit_author_name
_audit_author_address
'Wen-Hua Sun'
;Institute of Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2018-12-26 deposited with the CCDC.	2019-02-13 downloaded from the CCDC.
;
_audit_creation_date             2018-06-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H17 Al Cl N O'
_chemical_formula_sum            'C12 H17 Al Cl N O'
_chemical_formula_weight         253.69
_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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'

_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      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   10.156(2)
_cell_length_b                   9.5875(19)
_cell_length_c                   13.196(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.05(3)
_cell_angle_gamma                90
_cell_volume                     1275.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4420
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4755
_cell_measurement_theta_min      1.5550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.47470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.427
_exptl_crystal_size_mid          0.419
_exptl_crystal_size_min          0.293
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15208
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_min         2.633
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2743
_reflns_number_total             2881
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2881
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0960P)²+0.7560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1528
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2)
2.d Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c), C12(H12a,H12b,H12c), C9(H9a,H9b,H9c), C10(H10a,H10b,H10c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.24369(5) 0.35952(6) 0.61519(4) 0.0391(2) Uani 1 1 d . . . . .
Al1 Al 0.60322(5) 0.27970(5) 0.74303(4) 0.02090(19) Uani 1 1 d . . . . .
O1 O 0.73884(13) 0.25846(14) 0.65999(9) 0.0217(3) Uani 1 1 d . . . . .
N1 N 0.48926(16) 0.32490(17) 0.58041(12) 0.0248(3) Uani 1 1 d . . . . .
C7 C 0.72273(19) 0.29367(18) 0.55491(13) 0.0221(4) Uani 1 1 d . . . . .
H7 H 0.761751 0.385865 0.546790 0.027 Uiso 1 1 calc R . . . .
C6 C 0.7751(2) 0.1909(2) 0.47724(14) 0.0250(4) Uani 1 1 d . . . . .
C8 C 0.5790(2) 0.29974(18) 0.51723(13) 0.0233(4) Uani 1 1 d . . . . .
C1 C 0.3641(2) 0.3244(2) 0.53704(15) 0.0272(4) Uani 1 1 d . . . . .
C4 C 0.5534(2) 0.2644(2) 0.41490(14) 0.0269(4) Uani 1 1 d . . . . .
C11 C 0.5484(2) 0.4629(2) 0.79236(14) 0.0270(4) Uani 1 1 d . . . . .
H11A H 0.535125 0.455582 0.862939 0.040 Uiso 1 1 calc GR . . . .
H11B H 0.467220 0.491545 0.752888 0.040 Uiso 1 1 calc GR . . . .
H11C H 0.616361 0.530564 0.785200 0.040 Uiso 1 1 calc GR . . . .
C3 C 0.4220(2) 0.2611(2) 0.37251(15) 0.0306(4) Uani 1 1 d . . . . .
H3 H 0.398701 0.236911 0.304419 0.037 Uiso 1 1 calc R . . . .
C2 C 0.3256(2) 0.2950(2) 0.43480(16) 0.0308(4) Uani 1 1 d . . . . .
H2 H 0.236510 0.297954 0.408200 0.037 Uiso 1 1 calc R . . . .
C12 C 0.4997(2) 0.1069(2) 0.74999(16) 0.0306(4) Uani 1 1 d . . . . .
H12A H 0.515440 0.046420 0.694763 0.046 Uiso 1 1 calc GR . . . .
H12B H 0.406997 0.129266 0.744762 0.046 Uiso 1 1 calc GR . . . .
H12C H 0.526301 0.060888 0.813833 0.046 Uiso 1 1 calc GR . . . .
C5 C 0.6828(2) 0.2285(2) 0.37721(14) 0.0290(4) Uani 1 1 d . . . . .
H5A H 0.717556 0.307396 0.342834 0.035 Uiso 1 1 calc R . . . .
H5B H 0.672844 0.149833 0.330709 0.035 Uiso 1 1 calc R . . . .
C9 C 0.7490(2) 0.0399(2) 0.50665(16) 0.0322(4) Uani 1 1 d . . . . .
H9A H 0.798717 0.019158 0.571548 0.048 Uiso 1 1 calc GR . . . .
H9B H 0.775857 -0.021907 0.455728 0.048 Uiso 1 1 calc GR . . . .
H9C H 0.656084 0.027633 0.511108 0.048 Uiso 1 1 calc GR . . . .
C10 C 0.9201(2) 0.2138(2) 0.46463(17) 0.0356(5) Uani 1 1 d . . . . .
H10A H 0.933291 0.309238 0.446241 0.053 Uiso 1 1 calc GR . . . .
H10B H 0.944547 0.153595 0.411923 0.053 Uiso 1 1 calc GR . . . .
H10C H 0.974045 0.193161 0.527757 0.053 Uiso 1 1 calc GR . . . .


_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
Cl1 C1 1.727(2) . ?
Al1 Al1 2.9646(12) 2_656 ?
Al1 O1 1.8735(14) . ?
Al1 O1 1.9361(16) 2_656 ?
Al1 N1 2.3500(17) . ?
Al1 C11 1.977(2) . ?
Al1 C12 1.970(2) . ?
O1 C7 1.417(2) . ?
N1 C8 1.331(2) . ?
N1 C1 1.328(3) . ?
C7 H7 0.9800 . ?
C7 C6 1.561(2) . ?
C7 C8 1.484(3) . ?
C6 C5 1.564(3) . ?
C6 C9 1.531(3) . ?
C6 C10 1.518(3) . ?
C8 C4 1.386(2) . ?
C1 C2 1.387(3) . ?
C4 C3 1.382(3) . ?
C4 C5 1.502(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C2 1.392(3) . ?
C2 H2 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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 Al1 39.67(4) . 2_656 ?
O1 Al1 Al1 38.15(4) 2_656 2_656 ?
O1 Al1 O1 76.48(6) . 2_656 ?
O1 Al1 N1 78.52(6) . . ?
O1 Al1 N1 153.92(6) 2_656 . ?
O1 Al1 C11 123.10(8) . . ?
O1 Al1 C11 96.88(7) 2_656 . ?
O1 Al1 C12 111.75(8) . . ?
O1 Al1 C12 106.51(8) 2_656 . ?
N1 Al1 Al1 115.82(5) . 2_656 ?
C11 Al1 Al1 107.53(6) . 2_656 ?
C11 Al1 N1 90.56(7) . . ?
C12 Al1 Al1 122.37(7) . 2_656 ?
C12 Al1 N1 89.53(8) . . ?
C12 Al1 C11 123.95(9) . . ?
Al1 O1 Al1 102.18(6) . 2_656 ?
C7 O1 Al1 127.48(11) . 2_656 ?
C7 O1 Al1 122.79(11) . . ?
C8 N1 Al1 103.90(12) . . ?
C1 N1 Al1 136.95(13) . . ?
C1 N1 C8 114.97(17) . . ?
O1 C7 H7 108.8 . . ?
O1 C7 C6 118.97(15) . . ?
O1 C7 C8 109.14(15) . . ?
C6 C7 H7 108.8 . . ?
C8 C7 H7 108.8 . . ?
C8 C7 C6 101.84(15) . . ?
C7 C6 C5 101.03(15) . . ?
C9 C6 C7 110.29(15) . . ?
C9 C6 C5 109.12(16) . . ?
C10 C6 C7 113.20(16) . . ?
C10 C6 C5 111.28(16) . . ?
C10 C6 C9 111.42(17) . . ?
N1 C8 C7 121.22(16) . . ?
N1 C8 C4 126.42(19) . . ?
C4 C8 C7 112.11(17) . . ?
N1 C1 Cl1 116.89(15) . . ?
N1 C1 C2 124.12(19) . . ?
C2 C1 Cl1 118.98(16) . . ?
C8 C4 C5 108.14(18) . . ?
C3 C4 C8 117.16(19) . . ?
C3 C4 C5 134.56(18) . . ?
Al1 C11 H11A 109.5 . . ?
Al1 C11 H11B 109.5 . . ?
Al1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C3 H3 121.0 . . ?
C4 C3 C2 118.01(18) . . ?
C2 C3 H3 121.0 . . ?
C1 C2 C3 119.1(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
Al1 C12 H12A 109.5 . . ?
Al1 C12 H12B 109.5 . . ?
Al1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C5 H5A 111.1 . . ?
C6 C5 H5B 111.1 . . ?
C4 C5 C6 103.39(15) . . ?
C4 C5 H5A 111.1 . . ?
C4 C5 H5B 111.1 . . ?
H5A C5 H5B 109.0 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
