# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_d19159
_audit_block_doi                 10.5517/ccdc.csd.cc1zcr03
_database_code_depnum_ccdc_archive 'CCDC 1828535'
_audit_update_record             
;
2018-03-09 deposited with the CCDC.
2018-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'LClHAlMe2 (4)'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 Al Cl N S'
_chemical_formula_sum            'C15 H15 Al Cl N S'
_chemical_formula_weight         303.77

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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                   11.8748(9)
_cell_length_b                   12.7887(10)
_cell_length_c                   11.2417(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.102(2)
_cell_angle_gamma                90.00
_cell_volume                     1519.74(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9770
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.028

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8395
_exptl_absorpt_correction_T_max  0.9663
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28773
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2685
_reflns_number_gt                2271
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0321P)²+0.9386P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2685
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0816
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7848(2) 0.36912(16) 0.6293(2) 0.0354(5) Uani 1 1 d . . .
H1A H 0.8595 0.3402 0.7049 0.053 Uiso 1 1 calc R . .
H1B H 0.7741 0.4425 0.6473 0.053 Uiso 1 1 calc R . .
H1C H 0.7958 0.3646 0.5481 0.053 Uiso 1 1 calc R . .
C2 C 0.6480(2) 0.14744(15) 0.6723(2) 0.0391(5) Uani 1 1 d . . .
H2A H 0.6338 0.1384 0.7471 0.047 Uiso 1 1 d R . .
H2B H 0.6134 0.0936 0.6130 0.047 Uiso 1 1 d R . .
H2C H 0.7237 0.1196 0.6958 0.047 Uiso 1 1 d R . .
C3 C 0.36040(19) 0.33181(15) 0.44163(18) 0.0276(4) Uani 1 1 d . . .
C4 C 0.2320(2) 0.32314(16) 0.3528(2) 0.0340(5) Uani 1 1 d . . .
H4 H 0.2074 0.3055 0.2622 0.041 Uiso 1 1 calc R . .
C5 C 0.1404(2) 0.33962(16) 0.3935(2) 0.0359(5) Uani 1 1 d . . .
H5 H 0.0534 0.3338 0.3315 0.043 Uiso 1 1 calc R . .
C6 C 0.17609(19) 0.36473(15) 0.5253(2) 0.0312(5) Uani 1 1 d . . .
C7 C 0.30149(18) 0.37578(14) 0.61612(19) 0.0271(4) Uani 1 1 d . . .
H7 H 0.3249 0.3930 0.7066 0.033 Uiso 1 1 calc R . .
C8 C 0.39352(17) 0.36133(14) 0.57345(18) 0.0240(4) Uani 1 1 d . . .
C9 C 0.55846(18) 0.43863(14) 0.75916(18) 0.0256(4) Uani 1 1 d . . .
H9 H 0.4950 0.4852 0.7562 0.031 Uiso 1 1 calc R . .
C10 C 0.68390(18) 0.44990(14) 0.86997(17) 0.0253(4) Uani 1 1 d . . .
C11 C 0.7173(2) 0.54541(16) 0.93664(19) 0.0346(5) Uani 1 1 d . . .
H11 H 0.6588 0.6018 0.9076 0.042 Uiso 1 1 calc R . .
C12 C 0.8344(2) 0.55866(17) 1.0443(2) 0.0439(6) Uani 1 1 d . . .
H12 H 0.8570 0.6244 1.0882 0.053 Uiso 1 1 calc R . .
C13 C 0.9189(2) 0.47680(17) 1.0886(2) 0.0419(6) Uani 1 1 d . . .
H13 H 0.9999 0.4864 1.1626 0.050 Uiso 1 1 calc R . .
C14 C 0.8864(2) 0.38108(16) 1.0258(2) 0.0359(5) Uani 1 1 d . . .
H14 H 0.9445 0.3245 1.0574 0.043 Uiso 1 1 calc R . .
C15 C 0.76963(19) 0.36719(15) 0.91706(18) 0.0293(4) Uani 1 1 d . . .
H15 H 0.7476 0.3010 0.8741 0.035 Uiso 1 1 calc R . .
Al1 Al 0.63512(5) 0.28958(4) 0.60417(5) 0.02488(15) Uani 1 1 d . . .
Cl1 Cl 0.06112(5) 0.37959(5) 0.57961(6) 0.04589(17) Uani 1 1 d . . .
N1 N 0.52548(14) 0.37085(11) 0.66414(14) 0.0225(3) Uani 1 1 d . . .
S1 S 0.47763(5) 0.30806(5) 0.39003(5) 0.03797(16) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0359(12) 0.0347(12) 0.0421(12) -0.0039(9) 0.0236(10) -0.0057(9)
C2 0.0542(15) 0.0262(11) 0.0508(13) -0.0002(9) 0.0360(12) 0.0012(10)
C3 0.0323(11) 0.0237(10) 0.0259(10) -0.0005(8) 0.0125(9) -0.0030(8)
C4 0.0357(12) 0.0317(11) 0.0259(10) 0.0007(8) 0.0062(9) -0.0052(9)
C5 0.0260(11) 0.0309(11) 0.0383(12) 0.0080(9) 0.0038(9) -0.0042(9)
C6 0.0248(11) 0.0246(10) 0.0444(12) 0.0105(9) 0.0160(9) 0.0018(8)
C7 0.0280(11) 0.0247(10) 0.0290(10) 0.0029(8) 0.0133(9) 0.0020(8)
C8 0.0245(10) 0.0199(9) 0.0252(9) 0.0016(7) 0.0092(8) -0.0010(8)
C9 0.0270(10) 0.0248(10) 0.0264(10) 0.0000(8) 0.0133(8) 0.0023(8)
C10 0.0283(11) 0.0259(10) 0.0231(9) -0.0008(8) 0.0130(8) -0.0008(8)
C11 0.0399(13) 0.0261(11) 0.0304(10) -0.0029(8) 0.0095(9) 0.0027(9)
C12 0.0507(15) 0.0283(11) 0.0360(12) -0.0067(9) 0.0052(11) -0.0089(10)
C13 0.0359(13) 0.0403(13) 0.0323(11) 0.0026(10) 0.0007(10) -0.0092(10)
C14 0.0310(12) 0.0360(12) 0.0333(11) 0.0069(9) 0.0083(9) 0.0050(9)
C15 0.0330(11) 0.0260(10) 0.0277(10) -0.0024(8) 0.0127(9) -0.0018(9)
Al1 0.0269(3) 0.0242(3) 0.0282(3) -0.0020(2) 0.0166(3) -0.0022(2)
Cl1 0.0294(3) 0.0493(3) 0.0642(4) 0.0174(3) 0.0259(3) 0.0077(2)
N1 0.0228(8) 0.0225(8) 0.0219(8) 0.0010(6) 0.0099(7) 0.0000(6)
S1 0.0386(3) 0.0519(4) 0.0250(3) -0.0066(2) 0.0158(2) -0.0013(3)

_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
C1 Al1 1.953(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 Al1 1.951(2) . ?
C2 H2A 0.9377 . ?
C2 H2B 0.9150 . ?
C2 H2C 0.8880 . ?
C3 C4 1.395(3) . ?
C3 C8 1.401(3) . ?
C3 S1 1.761(2) . ?
C4 C5 1.375(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.376(3) . ?
C6 Cl1 1.741(2) . ?
C7 C8 1.392(3) . ?
C7 H7 0.9500 . ?
C8 N1 1.433(2) . ?
C9 N1 1.290(2) . ?
C9 C10 1.449(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(3) . ?
C10 C15 1.394(3) . ?
C11 C12 1.376(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
Al1 N1 2.0074(16) . ?
Al1 S1 2.2904(8) . ?

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
Al1 C1 H1A 109.5 . . ?
Al1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
Al1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
Al1 C2 H2A 116.9 . . ?
Al1 C2 H2B 119.1 . . ?
H2A C2 H2B 110.8 . . ?
Al1 C2 H2C 112.3 . . ?
H2A C2 H2C 104.7 . . ?
H2B C2 H2C 88.4 . . ?
C4 C3 C8 117.88(19) . . ?
C4 C3 S1 121.34(15) . . ?
C8 C3 S1 120.78(15) . . ?
C5 C4 C3 121.43(19) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 119.38(19) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C7 C6 C5 121.25(19) . . ?
C7 C6 Cl1 119.03(16) . . ?
C5 C6 Cl1 119.70(16) . . ?
C6 C7 C8 119.02(18) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C7 C8 C3 120.96(17) . . ?
C7 C8 N1 121.29(16) . . ?
C3 C8 N1 117.68(17) . . ?
N1 C9 C10 125.72(17) . . ?
N1 C9 H9 117.1 . . ?
C10 C9 H9 117.1 . . ?
C11 C10 C15 118.77(18) . . ?
C11 C10 C9 118.60(17) . . ?
C15 C10 C9 122.52(17) . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 120.14(19) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 120.17(19) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 120.25(18) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
C2 Al1 C1 121.65(10) . . ?
C2 Al1 N1 107.32(8) . . ?
C1 Al1 N1 111.62(8) . . ?
C2 Al1 S1 112.90(8) . . ?
C1 Al1 S1 110.58(7) . . ?
N1 Al1 S1 87.46(5) . . ?
C9 N1 C8 117.85(16) . . ?
C9 N1 Al1 128.84(13) . . ?
C8 N1 Al1 112.54(11) . . ?
C3 S1 Al1 93.50(7) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.042
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
