# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_alsnphbr
_audit_block_doi                 10.5517/cc1j79sv
_database_code_depnum_ccdc_archive 'CCDC 1407207'
_audit_update_record             
;
2015-06-17 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        LHBrAlMe3
_chemical_name_common            alsnphbr
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 Al Br N S'
_chemical_formula_sum            'C16 H17 Al Br N S'
_chemical_formula_weight         362.26

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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7337(5)
_cell_length_b                   9.8376(8)
_cell_length_c                   10.2179(9)
_cell_angle_alpha                65.706(8)
_cell_angle_beta                 76.457(6)
_cell_angle_gamma                64.524(7)
_cell_volume                     803.12(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2840
_cell_measurement_theta_min      4.1470
_cell_measurement_theta_max      27.7720

_exptl_crystal_description       crystal
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    2.733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0690
_diffrn_reflns_number            9640
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0532
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3152
_reflns_number_gt                2623
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
;
_computing_cell_refinement       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
;
_computing_data_reduction        
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0417P)²+0.3183P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3152
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_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
Al Al 0.91517(10) 0.35706(12) -0.21798(11) 0.0191(2) Uani 1 1 d . . .
Br1 Br 0.75734(4) -0.06595(4) -0.53704(4) 0.02885(13) Uani 1 1 d . . .
S1 S 0.51295(9) 0.22656(10) 0.04531(9) 0.0223(2) Uani 1 1 d . . .
N1 N 0.7677(3) 0.2670(3) -0.0580(3) 0.0175(6) Uani 1 1 d . . .
C1 C 0.5814(3) 0.2994(4) 0.1331(4) 0.0200(7) Uani 1 1 d . . .
C2 C 0.5177(4) 0.3414(4) 0.2549(4) 0.0231(7) Uani 1 1 d . . .
H2A H 0.4231 0.3381 0.2975 0.028 Uiso 1 1 calc R . .
C3 C 0.5995(4) 0.3878(4) 0.3099(4) 0.0256(8) Uani 1 1 d . . .
H3A H 0.5583 0.4192 0.3895 0.031 Uiso 1 1 calc R . .
C4 C 0.7435(4) 0.3887(4) 0.2482(4) 0.0254(8) Uani 1 1 d . . .
H4A H 0.7984 0.4160 0.2900 0.030 Uiso 1 1 calc R . .
C5 C 0.8054(4) 0.3499(4) 0.1268(4) 0.0235(7) Uani 1 1 d . . .
H5A H 0.9007 0.3518 0.0856 0.028 Uiso 1 1 calc R . .
C6 C 0.7218(3) 0.3077(4) 0.0667(3) 0.0193(7) Uani 1 1 d . . .
C7 C 0.6693(3) 0.2171(4) -0.0771(4) 0.0190(7) Uani 1 1 d . . .
C8 C 0.6892(3) 0.1487(4) -0.1861(3) 0.0182(7) Uani 1 1 d . . .
C9 C 0.8341(3) 0.0536(4) -0.2258(4) 0.0223(7) Uani 1 1 d . . .
H9A H 0.9182 0.0339 -0.1824 0.027 Uiso 1 1 calc R . .
C10 C 0.8546(4) -0.0118(4) -0.3285(4) 0.0224(7) Uani 1 1 d . . .
H10A H 0.9517 -0.0743 -0.3555 0.027 Uiso 1 1 calc R . .
C11 C 0.7280(4) 0.0173(4) -0.3907(4) 0.0215(7) Uani 1 1 d . . .
C12 C 0.5823(4) 0.1071(4) -0.3510(4) 0.0231(7) Uani 1 1 d . . .
H12A H 0.4985 0.1240 -0.3928 0.028 Uiso 1 1 calc R . .
C13 C 0.5635(4) 0.1720(4) -0.2469(4) 0.0226(7) Uani 1 1 d . . .
H13A H 0.4660 0.2315 -0.2178 0.027 Uiso 1 1 calc R . .
C14 C 0.8848(4) 0.5588(4) -0.1951(4) 0.0271(8) Uani 1 1 d . . .
H14A H 0.9495 0.6087 -0.2660 0.041 Uiso 1 1 calc R . .
H14B H 0.9101 0.5346 -0.1006 0.041 Uiso 1 1 calc R . .
H14D H 0.7802 0.6308 -0.2077 0.041 Uiso 1 1 calc R . .
C15 C 1.1216(4) 0.1937(4) -0.1687(4) 0.0288(8) Uani 1 1 d . . .
H15A H 1.1959 0.2281 -0.2390 0.043 Uiso 1 1 calc R . .
H15D H 1.1286 0.0929 -0.1677 0.043 Uiso 1 1 calc R . .
H15B H 1.1405 0.1806 -0.0753 0.043 Uiso 1 1 calc R . .
C16 C 0.8421(4) 0.4079(4) -0.4041(4) 0.0232(7) Uani 1 1 d . . .
H16D H 0.9071 0.4502 -0.4816 0.035 Uiso 1 1 calc R . .
H16A H 0.7396 0.4864 -0.4119 0.035 Uiso 1 1 calc R . .
H16B H 0.8441 0.3117 -0.4091 0.035 Uiso 1 1 calc R . .


_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
Al C16 1.979(3) . ?
Al C15 1.976(3) . ?
Al C14 1.981(3) . ?
Al N1 2.079(3) . ?
Br1 C11 1.896(3) . ?
S1 C7 1.724(3) . ?
S1 C1 1.727(3) . ?
N1 C7 1.329(4) . ?
N1 C6 1.408(4) . ?
C1 C6 1.396(4) . ?
C1 C2 1.395(4) . ?
C2 C3 1.375(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.398(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.375(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.395(4) . ?
C5 H5A 0.9300 . ?
C7 C8 1.461(4) . ?
C8 C9 1.392(4) . ?
C8 C13 1.391(4) . ?
C9 C10 1.380(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.385(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.380(4) . ?
C12 C13 1.393(4) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14D 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15D 0.9600 . ?
C15 H15B 0.9600 . ?
C16 H16D 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 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
C16 Al C15 118.81(14) . . ?
C16 Al C14 109.74(15) . . ?
C15 Al C14 111.18(15) . . ?
C16 Al N1 106.55(12) . . ?
C15 Al N1 105.17(14) . . ?
C14 Al N1 104.14(13) . . ?
C7 S1 C1 90.19(15) . . ?
C7 N1 C6 110.1(3) . . ?
C7 N1 Al 125.3(2) . . ?
C6 N1 Al 120.8(2) . . ?
C6 C1 C2 121.4(3) . . ?
C6 C1 S1 109.7(2) . . ?
C2 C1 S1 128.8(2) . . ?
C3 C2 C1 117.7(3) . . ?
C3 C2 H2A 121.1 . . ?
C1 C2 H2A 121.1 . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 H3A 119.4 . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4A 119.4 . . ?
C3 C4 H4A 119.4 . . ?
C4 C5 C6 118.5(3) . . ?
C4 C5 H5A 120.8 . . ?
C6 C5 H5A 120.8 . . ?
C1 C6 C5 120.0(3) . . ?
C1 C6 N1 114.5(3) . . ?
C5 C6 N1 125.5(3) . . ?
N1 C7 C8 125.2(3) . . ?
N1 C7 S1 115.3(2) . . ?
C8 C7 S1 119.4(2) . . ?
C9 C8 C13 119.2(3) . . ?
C9 C8 C7 120.2(3) . . ?
C13 C8 C7 120.5(3) . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9A 119.6 . . ?
C8 C9 H9A 119.6 . . ?
C9 C10 C11 118.8(3) . . ?
C9 C10 H10A 120.6 . . ?
C11 C10 H10A 120.6 . . ?
C12 C11 C10 121.9(3) . . ?
C12 C11 Br1 119.4(2) . . ?
C10 C11 Br1 118.7(2) . . ?
C11 C12 C13 118.6(3) . . ?
C11 C12 H12A 120.7 . . ?
C13 C12 H12A 120.7 . . ?
C8 C13 C12 120.6(3) . . ?
C8 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
Al C14 H14A 109.5 . . ?
Al C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Al C14 H14D 109.5 . . ?
H14A C14 H14D 109.5 . . ?
H14B C14 H14D 109.5 . . ?
Al C15 H15A 109.5 . . ?
Al C15 H15D 109.5 . . ?
H15A C15 H15D 109.5 . . ?
Al C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15D C15 H15B 109.5 . . ?
Al C16 H16D 109.5 . . ?
Al C16 H16A 109.5 . . ?
H16D C16 H16A 109.5 . . ?
Al C16 H16B 109.5 . . ?
H16D C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.084
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
####################################################################### 
# 
# 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_alnsphme
_audit_block_doi                 10.5517/cc1j79tw
_database_code_depnum_ccdc_archive 'CCDC 1407208'
_audit_update_record             
;
2015-06-17 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        LHMeALMe3
_chemical_name_common            alnsphme
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H20 Al N S'
_chemical_formula_sum            'C17 H20 Al N S'
_chemical_formula_weight         297.38

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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4807(5)
_cell_length_b                   10.2653(5)
_cell_length_c                   11.1798(7)
_cell_angle_alpha                63.422(6)
_cell_angle_beta                 72.126(6)
_cell_angle_gamma                72.803(5)
_cell_volume                     813.96(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3138
_cell_measurement_theta_min      3.6000
_cell_measurement_theta_max      29.1020

_exptl_crystal_description       crystal
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96680
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0690
_diffrn_reflns_number            8139
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3201
_reflns_number_gt                2687
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
;
_computing_cell_refinement       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
;
_computing_data_reduction        
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0623P)²+0.6273P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3201
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1238
_refine_ls_wR_factor_gt          0.1169
_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
Al Al 1.23682(8) 0.19716(7) 0.23911(7) 0.01960(18) Uani 1 1 d . . .
S1 S 0.71834(7) 0.19109(6) 0.19901(6) 0.02349(17) Uani 1 1 d . . .
N1 N 1.0135(2) 0.15136(19) 0.24389(18) 0.0187(4) Uani 1 1 d . . .
C1 C 0.8636(3) 0.0373(2) 0.1838(2) 0.0207(5) Uani 1 1 d . . .
C2 C 0.8421(3) -0.0717(3) 0.1507(2) 0.0252(5) Uani 1 1 d . . .
H2A H 0.7422 -0.0656 0.1287 0.030 Uiso 1 1 calc R . .
C3 C 0.9746(3) -0.1888(3) 0.1519(2) 0.0279(5) Uani 1 1 d . . .
H3A H 0.9641 -0.2629 0.1302 0.034 Uiso 1 1 calc R . .
C4 C 1.1240(3) -0.1978(2) 0.1852(2) 0.0266(5) Uani 1 1 d . . .
H4A H 1.2108 -0.2785 0.1863 0.032 Uiso 1 1 calc R . .
C5 C 1.1460(3) -0.0893(2) 0.2166(2) 0.0245(5) Uani 1 1 d . . .
H5A H 1.2463 -0.0962 0.2385 0.029 Uiso 1 1 calc R . .
C6 C 1.0138(3) 0.0310(2) 0.2147(2) 0.0203(5) Uani 1 1 d . . .
C7 C 0.8644(3) 0.2387(2) 0.2440(2) 0.0196(4) Uani 1 1 d . . .
C8 C 0.8097(3) 0.3605(2) 0.2917(2) 0.0204(5) Uani 1 1 d . . .
C9 C 0.8562(3) 0.3417(3) 0.4085(2) 0.0245(5) Uani 1 1 d . . .
H9A H 0.9286 0.2559 0.4512 0.029 Uiso 1 1 calc R . .
C10 C 0.7946(3) 0.4506(3) 0.4612(2) 0.0284(5) Uani 1 1 d . . .
H10A H 0.8279 0.4374 0.5383 0.034 Uiso 1 1 calc R . .
C11 C 0.6844(3) 0.5788(3) 0.4009(2) 0.0267(5) Uani 1 1 d . . .
C12 C 0.6380(3) 0.5965(3) 0.2845(2) 0.0281(5) Uani 1 1 d . . .
H12A H 0.5645 0.6819 0.2426 0.034 Uiso 1 1 calc R . .
C13 C 0.6993(3) 0.4894(2) 0.2300(2) 0.0243(5) Uani 1 1 d . . .
H13A H 0.6670 0.5033 0.1521 0.029 Uiso 1 1 calc R . .
C14 C 0.6156(4) 0.6953(3) 0.4605(3) 0.0388(7) Uani 1 1 d . . .
H14A H 0.5418 0.7755 0.4061 0.058 Uiso 1 1 calc R . .
H14B H 0.7072 0.7318 0.4610 0.058 Uiso 1 1 calc R . .
H14C H 0.5542 0.6525 0.5523 0.058 Uiso 1 1 calc R . .
C15 C 1.3894(3) 0.1536(3) 0.0801(2) 0.0258(5) Uani 1 1 d . . .
H15A H 1.4996 0.1711 0.0678 0.039 Uiso 1 1 calc R . .
H15B H 1.3450 0.2170 -0.0009 0.039 Uiso 1 1 calc R . .
H15C H 1.3970 0.0519 0.0970 0.039 Uiso 1 1 calc R . .
C16 C 1.2791(3) 0.0577(3) 0.4220(2) 0.0273(5) Uani 1 1 d . . .
H16A H 1.3821 0.0682 0.4328 0.041 Uiso 1 1 calc R . .
H16B H 1.2883 -0.0419 0.4318 0.041 Uiso 1 1 calc R . .
H16C H 1.1873 0.0790 0.4904 0.041 Uiso 1 1 calc R . .
C17 C 1.2081(3) 0.4123(3) 0.1907(3) 0.0323(6) Uani 1 1 d . . .
H17A H 1.3117 0.4344 0.1883 0.049 Uiso 1 1 calc R . .
H17B H 1.1200 0.4399 0.2577 0.049 Uiso 1 1 calc R . .
H17C H 1.1788 0.4669 0.1025 0.049 Uiso 1 1 calc R . .


_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
Al C16 1.971(2) . ?
Al C17 1.980(2) . ?
Al C15 1.998(2) . ?
Al N1 2.0619(19) . ?
S1 C7 1.728(2) . ?
S1 C1 1.732(2) . ?
N1 C7 1.316(3) . ?
N1 C6 1.411(3) . ?
C1 C6 1.396(3) . ?
C1 C2 1.398(3) . ?
C2 C3 1.379(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.393(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.383(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.398(3) . ?
C5 H5A 0.9300 . ?
C7 C8 1.472(3) . ?
C8 C13 1.396(3) . ?
C8 C9 1.394(3) . ?
C9 C10 1.387(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.388(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.393(3) . ?
C11 C14 1.509(3) . ?
C12 C13 1.385(3) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C16 Al C17 118.52(11) . . ?
C16 Al C15 116.88(10) . . ?
C17 Al C15 107.54(11) . . ?
C16 Al N1 101.23(9) . . ?
C17 Al N1 109.03(10) . . ?
C15 Al N1 101.87(9) . . ?
C7 S1 C1 89.96(10) . . ?
C7 N1 C6 110.57(18) . . ?
C7 N1 Al 127.38(15) . . ?
C6 N1 Al 120.56(14) . . ?
C6 C1 C2 121.9(2) . . ?
C6 C1 S1 109.79(16) . . ?
C2 C1 S1 128.24(18) . . ?
C3 C2 C1 117.5(2) . . ?
C3 C2 H2A 121.2 . . ?
C1 C2 H2A 121.2 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C5 C4 C3 121.5(2) . . ?
C5 C4 H4A 119.3 . . ?
C3 C4 H4A 119.3 . . ?
C4 C5 C6 118.4(2) . . ?
C4 C5 H5A 120.8 . . ?
C6 C5 H5A 120.8 . . ?
C1 C6 C5 119.6(2) . . ?
C1 C6 N1 114.12(19) . . ?
C5 C6 N1 126.3(2) . . ?
N1 C7 C8 125.5(2) . . ?
N1 C7 S1 115.41(16) . . ?
C8 C7 S1 118.78(16) . . ?
C13 C8 C9 119.0(2) . . ?
C13 C8 C7 121.3(2) . . ?
C9 C8 C7 119.4(2) . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
C9 C10 C11 121.3(2) . . ?
C9 C10 H10A 119.4 . . ?
C11 C10 H10A 119.4 . . ?
C12 C11 C10 118.2(2) . . ?
C12 C11 C14 120.9(2) . . ?
C10 C11 C14 120.8(2) . . ?
C13 C12 C11 121.3(2) . . ?
C13 C12 H12A 119.4 . . ?
C11 C12 H12A 119.4 . . ?
C12 C13 C8 120.1(2) . . ?
C12 C13 H13A 120.0 . . ?
C8 C13 H13A 120.0 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Al C15 H15A 109.5 . . ?
Al C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
Al C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Al C16 H16A 109.5 . . ?
Al C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Al C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Al C17 H17A 109.5 . . ?
Al C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
Al C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.060
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
####################################################################### 
# 
# 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_ch16652
_database_code_depnum_ccdc_archive 'CCDC 1407261'
_audit_update_record             
;
2016-05-03 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H7 N S2'
_chemical_formula_sum            'C11 H7 N S2'
_chemical_formula_weight         217.30

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'
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'
Al Al 0.0645 0.0514 '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                   9.7682(5)
_cell_length_b                   12.6868(5)
_cell_length_c                   16.3518(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.613(2)
_cell_angle_gamma                90.00
_cell_volume                     1984.95(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5569
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      25.04

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.41
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8062
_exptl_absorpt_correction_T_max  0.8245
_exptl_absorpt_process_details   ?

_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  'Bruker APEX2'
_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            11137
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         25.08
_reflns_number_total             3519
_reflns_number_gt                2974
_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)+(0.1975P)²+9.3120P] 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         3519
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0981
_refine_ls_wR_factor_ref         0.3022
_refine_ls_wR_factor_gt          0.2818
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.002

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 0.3066(5) 0.8182(4) 0.0513(3) 0.0316(11) Uani 1 1 d . . .
C2 C 0.2515(6) 0.7359(4) -0.0058(4) 0.0375(13) Uani 1 1 d . . .
C3 C 0.2104(6) 0.7404(5) -0.0937(4) 0.0443(14) Uani 1 1 d . . .
H3 H 0.2151 0.8015 -0.1266 0.053 Uiso 1 1 calc R . .
C4 C 0.1615(7) 0.6408(6) -0.1255(4) 0.0511(16) Uani 1 1 d . . .
H4 H 0.1284 0.6278 -0.1833 0.061 Uiso 1 1 calc R . .
C5 C 0.1659(7) 0.5655(6) -0.0662(5) 0.0543(17) Uani 1 1 d . . .
H5 H 0.1368 0.4947 -0.0780 0.065 Uiso 1 1 calc R . .
C6 C 0.3797(5) 0.9025(4) 0.1701(3) 0.0324(12) Uani 1 1 d . . .
C7 C 0.4141(5) 0.9191(4) 0.2568(3) 0.0281(11) Uani 1 1 d . . .
H7 H 0.4084 0.8634 0.2947 0.034 Uiso 1 1 calc R . .
C8 C 0.4568(7) 1.0194(5) 0.2854(4) 0.0461(15) Uani 1 1 d . . .
H8 H 0.4784 1.0322 0.3438 0.055 Uiso 1 1 calc R . .
C9 C 0.4685(6) 1.1011(5) 0.2311(4) 0.0425(14) Uani 1 1 d . . .
H9 H 0.4986 1.1688 0.2522 0.051 Uiso 1 1 calc R . .
C10 C 0.4363(6) 1.0837(4) 0.1456(4) 0.0347(12) Uani 1 1 d . . .
H10 H 0.4448 1.1390 0.1078 0.042 Uiso 1 1 calc R . .
C11 C 0.3918(5) 0.9849(4) 0.1161(4) 0.0342(12) Uani 1 1 d . . .
C12 C 0.8870(6) 0.9098(5) 0.1283(4) 0.0424(14) Uani 1 1 d . . .
C13 C 0.9411(6) 0.9946(5) 0.1833(4) 0.0407(13) Uani 1 1 d . . .
C14 C 1.0655(5) 1.0579(4) 0.1858(3) 0.0318(11) Uani 1 1 d . . .
H14 H 1.1317 1.0488 0.1511 0.038 Uiso 1 1 calc R . .
C15 C 1.0717(7) 1.1366(5) 0.2496(4) 0.0479(15) Uani 1 1 d . . .
H15 H 1.1460 1.1860 0.2624 0.057 Uiso 1 1 calc R . .
C16 C 0.9635(8) 1.1350(6) 0.2902(4) 0.0524(16) Uani 1 1 d . . .
H16 H 0.9543 1.1837 0.3330 0.063 Uiso 1 1 calc R . .
C17 C 0.7477(6) 0.7842(4) 0.0643(4) 0.0390(13) Uani 1 1 d . . .
C18 C 0.6296(5) 0.7190(4) 0.0480(3) 0.0281(11) Uani 1 1 d . . .
H18 H 0.5624 0.7193 0.0828 0.034 Uiso 1 1 calc R . .
C19 C 0.6155(6) 0.6533(5) -0.0220(4) 0.0433(14) Uani 1 1 d . . .
H19 H 0.5373 0.6073 -0.0350 0.052 Uiso 1 1 calc R . .
C20 C 0.7128(7) 0.6539(5) -0.0725(4) 0.0454(14) Uani 1 1 d . . .
H20 H 0.7018 0.6107 -0.1208 0.055 Uiso 1 1 calc R . .
C21 C 0.8351(6) 0.7244(5) -0.0485(4) 0.0454(16) Uani 1 1 d . . .
H21 H 0.9069 0.7244 -0.0799 0.054 Uiso 1 1 calc R . .
C22 C 0.8433(6) 0.7833(5) 0.0128(5) 0.0500(17) Uani 1 1 d . . .
N1 N 0.3303(4) 0.8073(4) 0.1314(3) 0.0333(10) Uani 1 1 d . . .
N2 N 0.7728(6) 0.8592(4) 0.1324(4) 0.0551(16) Uani 1 1 d . . .
S1 S 0.34038(14) 0.94168(11) 0.01285(8) 0.0364(4) Uani 1 1 d . . .
S2 S 0.2284(2) 0.61120(12) 0.03078(11) 0.0511(5) Uani 1 1 d . . .
S3 S 0.97367(17) 0.87718(14) 0.04823(11) 0.0497(5) Uani 1 1 d . . .
S4 S 0.8467(2) 1.03828(17) 0.25743(12) 0.0604(6) Uani 1 1 d . . .


_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 N1 1.291(7) . ?
C1 C2 1.431(8) . ?
C1 S1 1.744(5) . ?
C2 C3 1.414(8) . ?
C2 S2 1.722(6) . ?
C3 C4 1.412(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.357(10) . ?
C4 H4 0.9500 . ?
C5 S2 1.683(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.404(7) . ?
C6 C11 1.389(8) . ?
C6 N1 1.404(7) . ?
C7 C8 1.390(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(8) . ?
C10 H10 0.9500 . ?
C11 S1 1.750(6) . ?
C12 N2 1.301(8) . ?
C12 C13 1.434(9) . ?
C12 S3 1.746(7) . ?
C13 C14 1.450(8) . ?
C13 S4 1.753(7) . ?
C14 C15 1.436(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.357(10) . ?
C15 H15 0.9500 . ?
C16 S4 1.688(7) . ?
C16 H16 0.9500 . ?
C17 C22 1.377(9) . ?
C17 C18 1.402(7) . ?
C17 N2 1.448(9) . ?
C18 C19 1.401(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.378(9) . ?
C19 H19 0.9500 . ?
C20 C21 1.480(10) . ?
C20 H20 0.9500 . ?
C21 C22 1.239(10) . ?
C21 H21 0.9500 . ?
C22 S3 1.755(7) . ?

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
N1 C1 C2 123.4(5) . . ?
N1 C1 S1 117.0(4) . . ?
C2 C1 S1 119.6(4) . . ?
C1 C2 C3 128.8(6) . . ?
C1 C2 S2 120.1(5) . . ?
C3 C2 S2 111.1(4) . . ?
C4 C3 C2 110.1(6) . . ?
C4 C3 H3 124.9 . . ?
C2 C3 H3 124.9 . . ?
C5 C4 C3 114.0(6) . . ?
C5 C4 H4 123.0 . . ?
C3 C4 H4 123.0 . . ?
C4 C5 S2 112.6(5) . . ?
C4 C5 H5 123.7 . . ?
S2 C5 H5 123.7 . . ?
C7 C6 C11 119.7(5) . . ?
C7 C6 N1 125.1(5) . . ?
C11 C6 N1 115.2(5) . . ?
C6 C7 C8 118.1(5) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
C9 C8 C7 121.8(5) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 119.7(5) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 119.3(5) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C6 121.4(5) . . ?
C10 C11 S1 129.1(4) . . ?
C6 C11 S1 109.5(4) . . ?
N2 C12 C13 123.3(6) . . ?
N2 C12 S3 118.2(5) . . ?
C13 C12 S3 118.4(5) . . ?
C12 C13 C14 129.4(6) . . ?
C12 C13 S4 119.5(5) . . ?
C14 C13 S4 111.1(4) . . ?
C15 C14 C13 108.5(5) . . ?
C15 C14 H14 125.7 . . ?
C13 C14 H14 125.7 . . ?
C16 C15 C14 115.0(6) . . ?
C16 C15 H15 122.5 . . ?
C14 C15 H15 122.5 . . ?
C15 C16 S4 113.4(5) . . ?
C15 C16 H16 123.3 . . ?
S4 C16 H16 123.3 . . ?
C22 C17 C18 120.8(6) . . ?
C22 C17 N2 116.5(6) . . ?
C18 C17 N2 122.6(6) . . ?
C17 C18 C19 116.6(5) . . ?
C17 C18 H18 121.7 . . ?
C19 C18 H18 121.7 . . ?
C20 C19 C18 121.3(6) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 117.5(6) . . ?
C19 C20 H20 121.3 . . ?
C21 C20 H20 121.3 . . ?
C22 C21 C20 119.7(6) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C17 123.9(6) . . ?
C21 C22 S3 126.9(6) . . ?
C17 C22 S3 109.2(5) . . ?
C1 N1 C6 109.9(4) . . ?
C12 N2 C17 107.3(6) . . ?
C1 S1 C11 88.4(3) . . ?
C5 S2 C2 92.1(3) . . ?
C12 S3 C22 88.8(3) . . ?
C16 S4 C13 91.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.08
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         3.465
_refine_diff_density_min         -0.980
_refine_diff_density_rms         0.164

####################################################################### 
# 
# 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_a16651
_audit_block_doi                 10.5517/cc1j7crw
_database_code_depnum_ccdc_archive 'CCDC 1407268'
_audit_update_record             
;
2016-05-03 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 Al N S2'
_chemical_formula_sum            'C14 H16 Al N S2'
_chemical_formula_weight         289.38

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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2963(3)
_cell_length_b                   9.2804(4)
_cell_length_c                   10.3920(4)
_cell_angle_alpha                87.690(2)
_cell_angle_beta                 84.941(2)
_cell_angle_gamma                71.092(2)
_cell_volume                     753.93(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4387
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      25.05

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7840
_exptl_absorpt_correction_T_max  0.9361
_exptl_absorpt_process_details   ?

_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  'Bruker APEX2'
_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            6452
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2631
_reflns_number_gt                2401
_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)+(0.0754P)²+0.9792P] 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         2631
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1495
_refine_ls_wR_factor_gt          0.1376
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.000
_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 0.4064(3) 0.3673(3) 1.0703(3) 0.0233(6) Uani 1 1 d . . .
C2 C 0.3892(4) 0.4126(3) 1.1989(3) 0.0301(6) Uani 1 1 d . . .
H2 H 0.2897 0.4894 1.2329 0.036 Uiso 1 1 calc R . .
C3 C 0.5217(4) 0.3418(4) 1.2743(3) 0.0322(7) Uani 1 1 d . . .
H3 H 0.5139 0.3713 1.3617 0.039 Uiso 1 1 calc R . .
C4 C 0.6668(4) 0.2279(4) 1.2251(3) 0.0340(7) Uani 1 1 d . . .
H4 H 0.7550 0.1797 1.2801 0.041 Uiso 1 1 calc R . .
C5 C 0.6850(4) 0.1837(3) 1.0973(3) 0.0301(6) Uani 1 1 d . . .
H5 H 0.7844 0.1061 1.0643 0.036 Uiso 1 1 calc R . .
C6 C 0.5536(3) 0.2560(3) 1.0183(2) 0.0227(6) Uani 1 1 d . . .
C7 C 0.3998(3) 0.3034(3) 0.8449(3) 0.0225(6) Uani 1 1 d . . .
C8 C 0.3453(3) 0.2840(3) 0.7197(3) 0.0250(6) Uani 1 1 d . . .
C9 C 0.7442(4) 0.2130(4) 0.5957(3) 0.0359(7) Uani 1 1 d . . .
H9A H 0.7278 0.3224 0.5973 0.054 Uiso 1 1 calc R . .
H9B H 0.6437 0.1971 0.5635 0.054 Uiso 1 1 calc R . .
H9C H 0.8458 0.1623 0.5386 0.054 Uiso 1 1 calc R . .
C10 C 0.8098(5) -0.0935(4) 0.7956(3) 0.0405(8) Uani 1 1 d . . .
H10A H 0.8239 -0.1222 0.8868 0.061 Uiso 1 1 calc R . .
H10B H 0.9124 -0.1514 0.7428 0.061 Uiso 1 1 calc R . .
H10C H 0.7103 -0.1159 0.7687 0.061 Uiso 1 1 calc R . .
C11 C 0.9452(4) 0.2012(4) 0.8473(3) 0.0342(7) Uani 1 1 d . . .
H11A H 0.9166 0.3111 0.8314 0.051 Uiso 1 1 calc R . .
H11B H 1.0594 0.1487 0.8066 0.051 Uiso 1 1 calc R . .
H11C H 0.9436 0.1807 0.9406 0.051 Uiso 1 1 calc R . .
C13 C 0.3723(3) 0.1387(3) 0.6569(2) 0.0194(5) Uani 1 1 d . . .
H13 H 0.4369 0.0408 0.6870 0.023 Uiso 1 1 calc R . .
C14 C 0.1995(4) 0.3184(5) 0.5209(3) 0.0450(9) Uani 1 1 d . . .
H14 H 0.1355 0.3541 0.4480 0.054 Uiso 1 1 calc R . .
C15 C 0.2845(4) 0.1710(4) 0.5428(3) 0.0428(8) Uani 1 1 d . . .
H15 H 0.2857 0.0933 0.4856 0.051 Uiso 1 1 calc R . .
N1 N 0.5506(3) 0.2265(3) 0.8867(2) 0.0224(5) Uani 1 1 d . . .
Al1 Al 0.77507(10) 0.12626(9) 0.77304(8) 0.0237(3) Uani 1 1 d . . .
S1 S 0.25771(8) 0.42491(8) 0.95548(7) 0.0275(2) Uani 1 1 d . . .
S2 S 0.21797(12) 0.43392(10) 0.63574(8) 0.0433(3) Uani 1 1 d . . .


_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 C2 1.398(4) . ?
C1 C6 1.401(4) . ?
C1 S1 1.735(3) . ?
C2 C3 1.378(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(4) . ?
C5 H5 0.9500 . ?
C6 N1 1.409(3) . ?
C7 N1 1.325(3) . ?
C7 C8 1.451(4) . ?
C7 S1 1.728(3) . ?
C8 C13 1.464(4) . ?
C8 S2 1.710(3) . ?
C9 Al1 1.985(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 Al1 1.972(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 Al1 1.986(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 C15 1.417(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.341(5) . ?
C14 S2 1.685(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N1 Al1 2.075(2) . ?

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
C2 C1 C6 121.7(3) . . ?
C2 C1 S1 128.4(2) . . ?
C6 C1 S1 109.8(2) . . ?
C3 C2 C1 117.6(3) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 118.5(3) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 N1 126.2(3) . . ?
C1 C6 N1 114.1(2) . . ?
N1 C7 C8 124.8(2) . . ?
N1 C7 S1 115.4(2) . . ?
C8 C7 S1 119.6(2) . . ?
C7 C8 C13 126.1(2) . . ?
C7 C8 S2 121.8(2) . . ?
C13 C8 S2 111.72(19) . . ?
Al1 C9 H9A 109.5 . . ?
Al1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Al1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
Al1 C10 H10A 109.5 . . ?
Al1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
Al1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Al1 C11 H11A 109.5 . . ?
Al1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
Al1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C15 C13 C8 107.5(3) . . ?
C15 C13 H13 126.3 . . ?
C8 C13 H13 126.3 . . ?
C15 C14 S2 113.2(3) . . ?
C15 C14 H14 123.4 . . ?
S2 C14 H14 123.4 . . ?
C14 C15 C13 115.6(3) . . ?
C14 C15 H15 122.2 . . ?
C13 C15 H15 122.2 . . ?
C7 N1 C6 110.5(2) . . ?
C7 N1 Al1 126.38(18) . . ?
C6 N1 Al1 121.03(18) . . ?
C10 Al1 C11 115.82(14) . . ?
C10 Al1 C9 117.32(14) . . ?
C11 Al1 C9 107.54(14) . . ?
C10 Al1 N1 103.20(13) . . ?
C11 Al1 N1 103.80(11) . . ?
C9 Al1 N1 107.94(12) . . ?
C7 S1 C1 89.99(13) . . ?
C14 S2 C8 92.04(16) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.090

