# Electronic Supplementary Material (ESI) for Faraday Discussions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2216592'
loop_
_audit_author_name
_audit_author_address
'Marta E. G. Mosquera'
;University of Alcala
Spain
;
_audit_update_record             
;
2022-10-31 deposited with the CCDC.	2022-12-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT196_shelx               
;
PROBLEM: No TEMP record and _measurement_temperature .NE.        293 Degree
RESPONSE: Temperature is 200 Degree
;
# Added during the CSD deposition process: Monday 31 October 2022 01:04 PM
# end Validation Reply Form


_audit_creation_date             2022-10-29T11:32:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C11 H17 Al N Na O'
_chemical_formula_weight         229.22

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.5855(4)
_cell_length_b                   11.0763(5)
_cell_length_c                   13.1896(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.386(4)
_cell_angle_gamma                90
_cell_volume                     1381.62(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    66
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      19.56
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    1.102
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 7 6 0.099
-5 -8 -6 0.156
-1 -9 8 0.149
1 4 -2 0.119
6 -1 -1 0.046
-1 0 0 0.104


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_sortav_scale_factor_max   1.236
_exptl_sortav_scale_factor_min   0.842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_T_max  0.949

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_ub_11      0.01
_diffrn_orient_matrix_ub_12      0
_diffrn_orient_matrix_ub_13      0
_diffrn_orient_matrix_ub_21      0
_diffrn_orient_matrix_ub_22      0.01
_diffrn_orient_matrix_ub_23      0
_diffrn_orient_matrix_ub_31      0
_diffrn_orient_matrix_ub_32      0
_diffrn_orient_matrix_ub_33      0.01
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_number            29270
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.061
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             3171
_reflns_number_gt                2146
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0578P)²+0.1449P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3171
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.042
_refine_ls_wR_factor_ref         0.114
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.045

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.15788(6) 0.90684(5) 0.18004(4) 0.02820(16) Uani 1 1 d . . . . .
Na Na 0.06868(8) 0.87601(6) -0.07696(6) 0.0381(2) Uani 1 1 d . . . . .
N1 N -0.07315(15) 0.82747(14) 0.04662(11) 0.0305(3) Uani 1 1 d . . . . .
O1 O -0.02083(13) 0.92670(11) 0.10835(10) 0.0345(3) Uani 1 1 d . . . . .
C1 C 0.1453(3) 0.7834(2) 0.28728(17) 0.0408(5) Uani 1 1 d . . . . .
C2 C 0.1995(3) 1.0712(2) 0.23548(18) 0.0436(5) Uani 1 1 d . . . . .
C3 C 0.2886(2) 0.8563(2) 0.08530(17) 0.0421(5) Uani 1 1 d . . . . .
C4 C -0.2849(2) 0.85391(19) 0.12720(17) 0.0438(5) Uani 1 1 d . . . . .
H4A H -0.375162 0.814595 0.121354 0.066 Uiso 1 1 calc R U . . .
H4B H -0.236341 0.847427 0.196622 0.066 Uiso 1 1 calc R U . . .
H4C H -0.298588 0.937551 0.109201 0.066 Uiso 1 1 calc R U . . .
C10 C -0.19867(19) 0.79480(16) 0.05599(13) 0.0305(4) Uani 1 1 d . . . . .
C11 C -0.25673(19) 0.69163(16) -0.00958(14) 0.0327(4) Uani 1 1 d . . . . .
C12 C -0.4018(2) 0.6814(2) -0.04352(18) 0.0513(6) Uani 1 1 d . . . . .
H12 H -0.463019 0.739031 -0.024314 0.062 Uiso 1 1 calc R U . . .
C13 C -0.4553(3) 0.5858(2) -0.1057(2) 0.0665(7) Uani 1 1 d . . . . .
H13 H -0.552188 0.580365 -0.128485 0.08 Uiso 1 1 calc R U . . .
C14 C -0.3672(3) 0.4994(2) -0.13374(19) 0.0600(7) Uani 1 1 d . . . . .
H14 H -0.403703 0.435187 -0.175163 0.072 Uiso 1 1 calc R U . . .
C15 C -0.2246(3) 0.5085(2) -0.10027(18) 0.0554(6) Uani 1 1 d . . . . .
H15 H -0.164148 0.450131 -0.119465 0.067 Uiso 1 1 calc R U . . .
C16 C -0.1698(2) 0.60285(18) -0.03859(16) 0.0431(5) Uani 1 1 d . . . . .
H16 H -0.072839 0.607021 -0.016037 0.052 Uiso 1 1 calc R U . . .
H2A H 0.199(3) 1.133(2) 0.184(2) 0.059(7) Uiso 1 1 d . . . . .
H2B H 0.135(3) 1.100(2) 0.273(2) 0.070(8) Uiso 1 1 d . . . . .
H3A H 0.297(3) 0.918(2) 0.026(2) 0.069(7) Uiso 1 1 d . . . . .
H3C H 0.268(3) 0.782(2) 0.0516(18) 0.057(7) Uiso 1 1 d . . . . .
H1B H 0.092(4) 0.808(3) 0.331(3) 0.121(14) Uiso 1 1 d . . . . .
H1A H 0.103(3) 0.715(3) 0.265(2) 0.080(9) Uiso 1 1 d . . . . .
H2C H 0.289(3) 1.074(2) 0.275(2) 0.073(8) Uiso 1 1 d . . . . .
H3B H 0.389(3) 0.846(2) 0.129(2) 0.078(8) Uiso 1 1 d . . . . .
H1C H 0.237(4) 0.756(3) 0.327(2) 0.099(10) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.8299(13) . ?
Al1 C2 1.978(2) . ?
Al1 C1 1.985(2) . ?
Al1 C3 1.989(2) . ?
Al1 Na 3.3743(9) 3_575 ?
Al1 Na 3.3753(9) . ?
Na O1 2.2573(14) 3_575 ?
Na N1 2.3489(17) . ?
Na C1 2.701(2) 4_575 ?
Na C3 2.757(2) . ?
Na O1 2.7766(15) . ?
Na C2 3.094(2) 3_575 ?
Na Na 3.7777(14) 3_575 ?
N1 C10 1.282(2) . ?
N1 O1 1.4104(19) . ?
C4 C10 1.499(3) . ?
C10 C11 1.486(3) . ?
C11 C16 1.382(3) . ?
C11 C12 1.394(3) . ?
C12 C13 1.385(3) . ?
C13 C14 1.367(4) . ?
C14 C15 1.370(4) . ?
C15 C16 1.375(3) . ?

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 C2 101.30(8) . . ?
O1 Al1 C1 106.88(9) . . ?
C2 Al1 C1 113.73(10) . . ?
O1 Al1 C3 109.98(8) . . ?
C2 Al1 C3 112.44(11) . . ?
C1 Al1 C3 111.81(10) . . ?
O1 Al1 Na 38.69(4) . 3_575 ?
C2 Al1 Na 64.59(7) . 3_575 ?
C1 Al1 Na 131.91(8) . 3_575 ?
C3 Al1 Na 112.19(7) . 3_575 ?
O1 Al1 Na 55.30(5) . . ?
C2 Al1 Na 117.85(7) . . ?
C1 Al1 Na 127.67(7) . . ?
C3 Al1 Na 54.75(7) . . ?
Na Al1 Na 68.07(2) 3_575 . ?
O1 Na N1 103.04(6) 3_575 . ?
O1 Na C1 125.49(7) 3_575 4_575 ?
N1 Na C1 124.13(7) . 4_575 ?
O1 Na C3 109.03(6) 3_575 . ?
N1 Na C3 84.19(6) . . ?
C1 Na C3 101.93(7) 4_575 . ?
O1 Na O1 83.28(5) 3_575 . ?
N1 Na O1 30.51(4) . . ?
C1 Na O1 150.73(7) 4_575 . ?
C3 Na O1 68.87(5) . . ?
O1 Na C2 64.62(5) 3_575 3_575 ?
N1 Na C2 90.06(7) . 3_575 ?
C1 Na C2 87.79(7) 4_575 3_575 ?
C3 Na C2 170.28(7) . 3_575 ?
O1 Na C2 102.40(6) . 3_575 ?
O1 Na Al1 30.45(3) 3_575 3_575 ?
N1 Na Al1 92.03(4) . 3_575 ?
C1 Na Al1 115.19(6) 4_575 3_575 ?
C3 Na Al1 136.86(6) . 3_575 ?
O1 Na Al1 86.54(3) . 3_575 ?
C2 Na Al1 35.27(4) 3_575 3_575 ?
O1 Na Al1 95.56(4) 3_575 . ?
N1 Na Al1 53.61(4) . . ?
C1 Na Al1 132.87(6) 4_575 . ?
C3 Na Al1 36.10(5) . . ?
O1 Na Al1 32.81(3) . . ?
C2 Na Al1 134.92(6) 3_575 . ?
Al1 Na Al1 111.93(2) 3_575 . ?
O1 Na Na 46.88(4) 3_575 3_575 ?
N1 Na Na 60.10(4) . 3_575 ?
C1 Na Na 171.14(6) 4_575 3_575 ?
C3 Na Na 85.98(5) . 3_575 ?
O1 Na Na 36.40(3) . 3_575 ?
C2 Na Na 84.36(5) 3_575 3_575 ?
Al1 Na Na 55.98(2) 3_575 3_575 ?
Al1 Na Na 55.95(2) . 3_575 ?
C10 N1 O1 114.55(15) . . ?
C10 N1 Na 142.21(12) . . ?
O1 N1 Na 91.76(9) . . ?
N1 O1 Al1 114.80(10) . . ?
N1 O1 Na 127.30(9) . 3_575 ?
Al1 O1 Na 110.87(6) . 3_575 ?
N1 O1 Na 57.73(8) . . ?
Al1 O1 Na 91.89(6) . . ?
Na O1 Na 96.72(5) 3_575 . ?
Al1 C1 Na 167.86(12) . 4_576 ?
Al1 C2 Na 80.14(7) . 3_575 ?
Al1 C3 Na 89.16(8) . . ?
N1 C10 C11 115.43(16) . . ?
N1 C10 C4 124.03(17) . . ?
C11 C10 C4 120.54(17) . . ?
C16 C11 C12 117.87(18) . . ?
C16 C11 C10 121.53(17) . . ?
C12 C11 C10 120.60(18) . . ?
C13 C12 C11 120.4(2) . . ?
C14 C13 C12 120.6(2) . . ?
C13 C14 C15 119.3(2) . . ?
C14 C15 C16 120.7(2) . . ?
C15 C16 C11 121.0(2) . . ?


# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
