# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2b

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H35 Al N2'
_chemical_formula_weight         366.51

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.075(3)
_cell_length_b                   17.439(6)
_cell_length_c                   13.495(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.666(4)
_cell_angle_gamma                90
_cell_volume                     2283.0(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    822
_cell_measurement_theta_min      2.336
_cell_measurement_theta_max      21.600

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.066
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.753
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10240
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.954
_diffrn_reflns_theta_max         26.010
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4494
_reflns_number_gt                2489
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0644P)²] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4494
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1287
_refine_ls_wR_factor_gt          0.1140
_refine_ls_goodness_of_fit_ref   0.902
_refine_ls_restrained_S_all      0.902
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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 0.32317(6) 0.22722(4) 0.43287(5) 0.0545(2) Uani 1 1 d . . . . .
N1 N -0.14923(16) 0.24748(9) 0.31401(13) 0.0495(4) Uani 1 1 d . . . . .
N2 N 0.16828(17) 0.30933(10) 0.38116(13) 0.0453(4) Uani 1 1 d . . . . .
H2 H 0.1112(19) 0.2911(10) 0.4125(14) 0.039(5) Uiso 1 1 d . . . . .
C1 C -0.2412(2) 0.23590(13) 0.38022(19) 0.0653(6) Uani 1 1 d . . . . .
H1A H -0.3357 0.2321 0.3383 0.078 Uiso 1 1 calc R U . . .
H1B H -0.2346 0.2793 0.4262 0.078 Uiso 1 1 calc R U . . .
C2 C -0.2018(3) 0.16372(14) 0.4420(2) 0.0820(8) Uani 1 1 d . . . . .
H2A H -0.2640 0.1558 0.4847 0.098 Uiso 1 1 calc R U . . .
H2B H -0.1092 0.1690 0.4869 0.098 Uiso 1 1 calc R U . . .
C3 C -0.2075(3) 0.09462(15) 0.3725(2) 0.0979(9) Uani 1 1 d . . . . .
H3A H -0.3026 0.0838 0.3361 0.118 Uiso 1 1 calc R U . . .
H3B H -0.1705 0.0501 0.4139 0.118 Uiso 1 1 calc R U . . .
C4 C -0.1247(3) 0.10957(13) 0.2952(2) 0.0785(8) Uani 1 1 d . . . . .
H4A H -0.0273 0.1116 0.3309 0.094 Uiso 1 1 calc R U . . .
H4B H -0.1389 0.0678 0.2460 0.094 Uiso 1 1 calc R U . . .
C5 C -0.1675(2) 0.18381(11) 0.23937(17) 0.0601(6) Uani 1 1 d . . . . .
H5A H -0.1122 0.1931 0.1919 0.072 Uiso 1 1 calc R U . . .
H5B H -0.2634 0.1808 0.2000 0.072 Uiso 1 1 calc R U . . .
C6 C -0.1595(2) 0.32059(11) 0.26490(15) 0.0467(5) Uani 1 1 d . . . . .
C7 C -0.2792(2) 0.36333(13) 0.23993(17) 0.0597(6) Uani 1 1 d . . . . .
H7A H -0.3580 0.3443 0.2547 0.072 Uiso 1 1 calc R U . . .
C8 C -0.2832(3) 0.43379(14) 0.19331(19) 0.0738(7) Uani 1 1 d . . . . .
H8A H -0.3644 0.4622 0.1778 0.089 Uiso 1 1 calc R U . . .
C9 C -0.1703(3) 0.46228(14) 0.16981(19) 0.0753(7) Uani 1 1 d . . . . .
H9A H -0.1736 0.5097 0.1377 0.090 Uiso 1 1 calc R U . . .
C10 C -0.0508(2) 0.42004(13) 0.19415(17) 0.0635(6) Uani 1 1 d . . . . .
H10A H 0.0266 0.4395 0.1778 0.076 Uiso 1 1 calc R U . . .
C11 C -0.0421(2) 0.34980(11) 0.24198(15) 0.0478(5) Uani 1 1 d . . . . .
C12 C 0.09209(19) 0.30608(12) 0.26860(15) 0.0510(5) Uani 1 1 d . . . . .
H12A H 0.0734 0.2529 0.2487 0.061 Uiso 1 1 calc R U . . .
H12B H 0.1509 0.3267 0.2288 0.061 Uiso 1 1 calc R U . . .
C13 C 0.20274(19) 0.38642(11) 0.42242(14) 0.0446(5) Uani 1 1 d . . . . .
C14 C 0.1486(2) 0.41051(12) 0.50179(15) 0.0521(5) Uani 1 1 d . . . . .
C15 C 0.0549(2) 0.36067(13) 0.54427(17) 0.0673(6) Uani 1 1 d . . . . .
H15A H 0.0298 0.3874 0.5988 0.101 Uiso 1 1 calc R U . . .
H15B H 0.1018 0.3140 0.5706 0.101 Uiso 1 1 calc R U . . .
H15C H -0.0267 0.3489 0.4906 0.101 Uiso 1 1 calc R U . . .
C16 C 0.1859(2) 0.48225(14) 0.54463(18) 0.0683(7) Uani 1 1 d . . . . .
H16A H 0.1516 0.4992 0.5982 0.082 Uiso 1 1 calc R U . . .
C17 C 0.2724(2) 0.52824(14) 0.5091(2) 0.0742(7) Uani 1 1 d . . . . .
H17A H 0.2947 0.5767 0.5375 0.089 Uiso 1 1 calc R U . . .
C18 C 0.3264(2) 0.50362(13) 0.43218(19) 0.0645(6) Uani 1 1 d . . . . .
H18A H 0.3859 0.5355 0.4092 0.077 Uiso 1 1 calc R U . . .
C19 C 0.2939(2) 0.43183(12) 0.38760(16) 0.0518(5) Uani 1 1 d . . . . .
C20 C 0.3629(2) 0.40753(13) 0.30661(18) 0.0685(7) Uani 1 1 d . . . . .
H20A H 0.3316 0.3572 0.2822 0.103 Uiso 1 1 calc R U . . .
H20B H 0.4610 0.4067 0.3357 0.103 Uiso 1 1 calc R U . . .
H20C H 0.3401 0.4432 0.2503 0.103 Uiso 1 1 calc R U . . .
C21 C 0.2371(3) 0.16127(13) 0.51585(19) 0.0775(7) Uani 1 1 d . . . . .
H21A H 0.2987 0.1201 0.5448 0.116 Uiso 1 1 calc R U . . .
H21B H 0.1527 0.1406 0.4731 0.116 Uiso 1 1 calc R U . . .
H21C H 0.2178 0.1909 0.5703 0.116 Uiso 1 1 calc R U . . .
C22 C 0.3486(3) 0.17723(14) 0.30896(19) 0.0762(7) Uani 1 1 d . . . . .
H22A H 0.4194 0.1390 0.3285 0.114 Uiso 1 1 calc R U . . .
H22B H 0.3751 0.2148 0.2659 0.114 Uiso 1 1 calc R U . . .
H22C H 0.2638 0.1534 0.2719 0.114 Uiso 1 1 calc R U . . .
C23 C 0.4819(2) 0.28237(14) 0.5202(2) 0.0777(7) Uani 1 1 d . . . . .
H23A H 0.5566 0.2471 0.5456 0.117 Uiso 1 1 calc R U . . .
H23B H 0.4565 0.3053 0.5771 0.117 Uiso 1 1 calc R U . . .
H23C H 0.5104 0.3217 0.4805 0.117 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 C23 1.963(2) . ?
Al1 C21 1.963(2) . ?
Al1 C22 1.963(2) . ?
Al1 N2 2.0939(18) . ?
N1 C6 1.428(2) . ?
N1 C1 1.464(3) . ?
N1 C5 1.477(2) . ?
N2 C13 1.461(2) . ?
N2 C12 1.507(2) . ?
N2 H2 0.862(17) . ?
C1 C2 1.503(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.518(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.524(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.502(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.380(3) . ?
C6 C11 1.397(3) . ?
C7 C8 1.376(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.356(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.373(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.376(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.509(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C19 1.387(3) . ?
C13 C14 1.392(3) . ?
C14 C16 1.387(3) . ?
C14 C15 1.506(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.363(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.365(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.389(3) . ?
C18 H18A 0.9300 . ?
C19 C20 1.506(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C23 Al1 C21 111.01(11) . . ?
C23 Al1 C22 117.12(11) . . ?
C21 Al1 C22 113.91(12) . . ?
C23 Al1 N2 106.15(9) . . ?
C21 Al1 N2 100.75(9) . . ?
C22 Al1 N2 106.08(9) . . ?
C6 N1 C1 115.32(16) . . ?
C6 N1 C5 112.01(16) . . ?
C1 N1 C5 109.23(17) . . ?
C13 N2 C12 115.02(16) . . ?
C13 N2 Al1 115.04(12) . . ?
C12 N2 Al1 116.18(12) . . ?
C13 N2 H2 105.9(12) . . ?
C12 N2 H2 104.8(12) . . ?
Al1 N2 H2 96.8(12) . . ?
N1 C1 C2 109.75(19) . . ?
N1 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C1 C2 C3 111.2(2) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C2 C3 C4 110.5(2) . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 110.8(2) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
N1 C5 C4 109.87(19) . . ?
N1 C5 H5A 109.7 . . ?
C4 C5 H5A 109.7 . . ?
N1 C5 H5B 109.7 . . ?
C4 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C7 C6 C11 119.0(2) . . ?
C7 C6 N1 123.03(19) . . ?
C11 C6 N1 117.94(17) . . ?
C8 C7 C6 120.7(2) . . ?
C8 C7 H7A 119.7 . . ?
C6 C7 H7A 119.7 . . ?
C9 C8 C7 120.8(2) . . ?
C9 C8 H8A 119.6 . . ?
C7 C8 H8A 119.6 . . ?
C8 C9 C10 119.0(2) . . ?
C8 C9 H9A 120.5 . . ?
C10 C9 H9A 120.5 . . ?
C9 C10 C11 122.0(2) . . ?
C9 C10 H10A 119.0 . . ?
C11 C10 H10A 119.0 . . ?
C10 C11 C6 118.55(19) . . ?
C10 C11 C12 120.05(19) . . ?
C6 C11 C12 121.40(18) . . ?
N2 C12 C11 113.63(15) . . ?
N2 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
N2 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C19 C13 C14 121.42(19) . . ?
C19 C13 N2 120.48(17) . . ?
C14 C13 N2 117.97(18) . . ?
C16 C14 C13 118.3(2) . . ?
C16 C14 C15 119.3(2) . . ?
C13 C14 C15 122.35(19) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C14 120.8(2) . . ?
C17 C16 H16A 119.6 . . ?
C14 C16 H16A 119.6 . . ?
C16 C17 C18 120.4(2) . . ?
C16 C17 H17A 119.8 . . ?
C18 C17 H17A 119.8 . . ?
C17 C18 C19 121.1(2) . . ?
C17 C18 H18A 119.4 . . ?
C19 C18 H18A 119.4 . . ?
C13 C19 C18 117.9(2) . . ?
C13 C19 C20 124.25(19) . . ?
C18 C19 C20 117.8(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Al1 C21 H21A 109.5 . . ?
Al1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
Al1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Al1 C22 H22A 109.5 . . ?
Al1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
Al1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Al1 C23 H23A 109.5 . . ?
Al1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
Al1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C6 N1 C1 C2 -169.39(19) . . . . ?
C5 N1 C1 C2 63.4(2) . . . . ?
N1 C1 C2 C3 -58.0(3) . . . . ?
C1 C2 C3 C4 51.9(3) . . . . ?
C2 C3 C4 C5 -51.9(3) . . . . ?
C6 N1 C5 C4 167.28(18) . . . . ?
C1 N1 C5 C4 -63.7(2) . . . . ?
C3 C4 C5 N1 57.8(3) . . . . ?
C1 N1 C6 C7 -28.7(3) . . . . ?
C5 N1 C6 C7 97.0(2) . . . . ?
C1 N1 C6 C11 150.92(19) . . . . ?
C5 N1 C6 C11 -83.3(2) . . . . ?
C11 C6 C7 C8 -0.1(3) . . . . ?
N1 C6 C7 C8 179.5(2) . . . . ?
C6 C7 C8 C9 0.8(4) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
C9 C10 C11 C6 0.9(3) . . . . ?
C9 C10 C11 C12 -179.1(2) . . . . ?
C7 C6 C11 C10 -0.7(3) . . . . ?
N1 C6 C11 C10 179.66(18) . . . . ?
C7 C6 C11 C12 179.27(18) . . . . ?
N1 C6 C11 C12 -0.4(3) . . . . ?
C13 N2 C12 C11 -58.1(2) . . . . ?
Al1 N2 C12 C11 163.28(14) . . . . ?
C10 C11 C12 N2 103.8(2) . . . . ?
C6 C11 C12 N2 -76.2(2) . . . . ?
C12 N2 C13 C19 -64.9(2) . . . . ?
Al1 N2 C13 C19 74.1(2) . . . . ?
C12 N2 C13 C14 119.18(19) . . . . ?
Al1 N2 C13 C14 -101.76(17) . . . . ?
C19 C13 C14 C16 1.2(3) . . . . ?
N2 C13 C14 C16 177.07(18) . . . . ?
C19 C13 C14 C15 -177.00(19) . . . . ?
N2 C13 C14 C15 -1.1(3) . . . . ?
C13 C14 C16 C17 0.6(3) . . . . ?
C15 C14 C16 C17 178.9(2) . . . . ?
C14 C16 C17 C18 -1.6(4) . . . . ?
C16 C17 C18 C19 0.6(4) . . . . ?
C14 C13 C19 C18 -2.1(3) . . . . ?
N2 C13 C19 C18 -177.84(18) . . . . ?
C14 C13 C19 C20 176.18(19) . . . . ?
N2 C13 C19 C20 0.4(3) . . . . ?
C17 C18 C19 C13 1.2(3) . . . . ?
C17 C18 C19 C20 -177.2(2) . . . . ?

_refine_diff_density_max         0.261
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.032

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 983597'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3b

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H31 Al N2'
_chemical_formula_weight         350.47

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.880(3)
_cell_length_b                   13.970(5)
_cell_length_c                   18.482(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2034.5(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    867
_cell_measurement_theta_min      2.810
_cell_measurement_theta_max      25.072

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.507
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9756
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.827
_diffrn_reflns_theta_max         27.010
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4339
_reflns_number_gt                3395
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_max     0.958
_reflns_Friedel_fraction_full    0.997

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0577P)²] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1233 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.22(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4339
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0972
_refine_ls_wR_factor_gt          0.0919
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_restrained_S_all      0.936
_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_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 0.31305(9) 0.48528(5) 0.19527(4) 0.04696(19) Uani 1 1 d . . . . .
N1 N 0.0515(2) 0.46533(13) 0.19385(11) 0.0452(4) Uani 1 1 d . . . . .
N2 N 0.3144(2) 0.55626(13) 0.11279(9) 0.0436(4) Uani 1 1 d . . . . .
C1 C 0.3920(4) 0.3512(2) 0.19326(18) 0.0734(8) Uani 1 1 d . . . . .
H1A H 0.3355 0.3175 0.1549 0.110 Uiso 1 1 calc R U . . .
H1B H 0.3665 0.3211 0.2387 0.110 Uiso 1 1 calc R U . . .
H1C H 0.5123 0.3498 0.1852 0.110 Uiso 1 1 calc R U . . .
C2 C 0.4157(4) 0.5559(2) 0.27628(15) 0.0688(8) Uani 1 1 d . . . . .
H2A H 0.5186 0.5860 0.2603 0.103 Uiso 1 1 calc R U . . .
H2B H 0.4407 0.5123 0.3150 0.103 Uiso 1 1 calc R U . . .
H2C H 0.3379 0.6039 0.2931 0.103 Uiso 1 1 calc R U . . .
C3 C -0.0579(3) 0.55353(18) 0.19142(14) 0.0501(6) Uani 1 1 d . . . . .
H3A H -0.1751 0.5346 0.1841 0.060 Uiso 1 1 calc R U . . .
H3B H -0.0241 0.5926 0.1505 0.060 Uiso 1 1 calc R U . . .
C4 C -0.0456(4) 0.6128(2) 0.25997(15) 0.0629(7) Uani 1 1 d . . . . .
H4A H 0.0683 0.6385 0.2642 0.075 Uiso 1 1 calc R U . . .
H4B H -0.1238 0.6663 0.2568 0.075 Uiso 1 1 calc R U . . .
C5 C -0.0864(5) 0.5545(3) 0.32685(16) 0.0766(9) Uani 1 1 d . . . . .
H5A H -0.0621 0.5920 0.3698 0.092 Uiso 1 1 calc R U . . .
H5B H -0.2063 0.5387 0.3272 0.092 Uiso 1 1 calc R U . . .
C6 C 0.0167(4) 0.4639(2) 0.32817(15) 0.0698(9) Uani 1 1 d . . . . .
H6A H -0.0196 0.4244 0.3685 0.084 Uiso 1 1 calc R U . . .
H6B H 0.1354 0.4797 0.3354 0.084 Uiso 1 1 calc R U . . .
C7 C -0.0028(4) 0.4085(2) 0.25866(15) 0.0619(7) Uani 1 1 d . . . . .
H7A H 0.0647 0.3505 0.2614 0.074 Uiso 1 1 calc R U . . .
H7B H -0.1206 0.3898 0.2529 0.074 Uiso 1 1 calc R U . . .
C8 C 0.0251(3) 0.41337(17) 0.12450(14) 0.0500(6) Uani 1 1 d . . . . .
C9 C -0.0623(4) 0.3271(2) 0.12270(18) 0.0687(8) Uani 1 1 d . . . . .
H9 H -0.1046 0.3013 0.1654 0.082 Uiso 1 1 calc R U . . .
C10 C -0.0873(5) 0.2792(2) 0.0581(2) 0.0858(11) Uani 1 1 d . . . . .
H10 H -0.1452 0.2212 0.0577 0.103 Uiso 1 1 calc R U . . .
C11 C -0.0275(4) 0.3167(3) -0.0048(2) 0.0861(11) Uani 1 1 d . . . . .
H11 H -0.0458 0.2852 -0.0484 0.103 Uiso 1 1 calc R U . . .
C12 C 0.0606(4) 0.4017(2) -0.00312(17) 0.0685(8) Uani 1 1 d . . . . .
H12 H 0.1018 0.4267 -0.0463 0.082 Uiso 1 1 calc R U . . .
C13 C 0.0902(3) 0.45164(18) 0.06068(13) 0.0501(6) Uani 1 1 d . . . . .
C14 C 0.1918(3) 0.54330(17) 0.05487(12) 0.0504(6) Uani 1 1 d . . . . .
H14A H 0.2514 0.5436 0.0090 0.061 Uiso 1 1 calc R U . . .
H14B H 0.1141 0.5971 0.0549 0.061 Uiso 1 1 calc R U . . .
C15 C 0.4535(3) 0.61586(17) 0.09273(12) 0.0423(5) Uani 1 1 d . . . . .
C16 C 0.5885(3) 0.57785(18) 0.05153(13) 0.0508(6) Uani 1 1 d . . . . .
C17 C 0.7216(3) 0.6361(2) 0.03219(14) 0.0639(8) Uani 1 1 d . . . . .
H17 H 0.8098 0.6109 0.0047 0.077 Uiso 1 1 calc R U . . .
C18 C 0.7276(4) 0.7305(2) 0.05251(16) 0.0687(8) Uani 1 1 d . . . . .
H18 H 0.8193 0.7687 0.0395 0.082 Uiso 1 1 calc R U . . .
C19 C 0.5962(4) 0.7678(2) 0.09241(15) 0.0628(7) Uani 1 1 d . . . . .
H19 H 0.6002 0.8316 0.1067 0.075 Uiso 1 1 calc R U . . .
C20 C 0.4575(3) 0.71214(18) 0.11190(13) 0.0492(6) Uani 1 1 d . . . . .
C21 C 0.5890(4) 0.4741(2) 0.03023(16) 0.0706(8) Uani 1 1 d . . . . .
H21A H 0.6807 0.4624 -0.0028 0.106 Uiso 1 1 calc R U . . .
H21B H 0.4833 0.4585 0.0073 0.106 Uiso 1 1 calc R U . . .
H21C H 0.6033 0.4352 0.0726 0.106 Uiso 1 1 calc R U . . .
C22 C 0.3114(4) 0.75694(18) 0.15197(16) 0.0649(7) Uani 1 1 d . . . . .
H22A H 0.2064 0.7372 0.1302 0.097 Uiso 1 1 calc R U . . .
H22B H 0.3207 0.8254 0.1496 0.097 Uiso 1 1 calc R U . . .
H22C H 0.3138 0.7368 0.2016 0.097 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 N2 1.8185(19) . ?
Al1 C2 1.967(3) . ?
Al1 C1 1.974(3) . ?
Al1 N1 2.080(2) . ?
N1 C8 1.488(3) . ?
N1 C7 1.499(3) . ?
N1 C3 1.505(3) . ?
N2 C15 1.425(3) . ?
N2 C14 1.453(3) . ?
C3 C4 1.517(4) . ?
C4 C5 1.515(4) . ?
C5 C6 1.505(5) . ?
C6 C7 1.508(4) . ?
C8 C9 1.388(4) . ?
C8 C13 1.393(4) . ?
C9 C10 1.383(5) . ?
C10 C11 1.359(5) . ?
C11 C12 1.375(5) . ?
C12 C13 1.390(4) . ?
C13 C14 1.514(4) . ?
C15 C20 1.391(3) . ?
C15 C16 1.412(3) . ?
C16 C17 1.375(4) . ?
C16 C21 1.502(4) . ?
C17 C18 1.372(4) . ?
C18 C19 1.374(4) . ?
C19 C20 1.388(4) . ?
C20 C22 1.505(4) . ?

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
N2 Al1 C2 111.22(12) . . ?
N2 Al1 C1 119.99(12) . . ?
C2 Al1 C1 111.15(14) . . ?
N2 Al1 N1 93.92(9) . . ?
C2 Al1 N1 118.96(12) . . ?
C1 Al1 N1 100.64(11) . . ?
C8 N1 C7 112.95(19) . . ?
C8 N1 C3 107.09(18) . . ?
C7 N1 C3 107.1(2) . . ?
C8 N1 Al1 102.39(15) . . ?
C7 N1 Al1 110.09(15) . . ?
C3 N1 Al1 117.28(14) . . ?
C15 N2 C14 113.09(17) . . ?
C15 N2 Al1 122.76(15) . . ?
C14 N2 Al1 123.07(15) . . ?
N1 C3 C4 112.7(2) . . ?
C5 C4 C3 112.0(2) . . ?
C6 C5 C4 110.6(2) . . ?
C5 C6 C7 111.3(2) . . ?
N1 C7 C6 112.3(2) . . ?
C9 C8 C13 119.7(2) . . ?
C9 C8 N1 120.9(2) . . ?
C13 C8 N1 119.4(2) . . ?
C10 C9 C8 120.7(3) . . ?
C11 C10 C9 120.2(3) . . ?
C10 C11 C12 119.2(3) . . ?
C11 C12 C13 122.5(3) . . ?
C12 C13 C8 117.6(2) . . ?
C12 C13 C14 117.0(2) . . ?
C8 C13 C14 125.4(2) . . ?
N2 C14 C13 113.87(19) . . ?
C20 C15 C16 118.9(2) . . ?
C20 C15 N2 121.1(2) . . ?
C16 C15 N2 120.0(2) . . ?
C17 C16 C15 119.5(3) . . ?
C17 C16 C21 120.1(3) . . ?
C15 C16 C21 120.4(2) . . ?
C18 C17 C16 121.6(3) . . ?
C17 C18 C19 119.1(3) . . ?
C18 C19 C20 121.4(3) . . ?
C19 C20 C15 119.5(3) . . ?
C19 C20 C22 119.8(2) . . ?
C15 C20 C22 120.7(2) . . ?

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.035

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 983598'
