# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# 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_cr1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C24 H46 Al4 N2 O2
;
_chemical_formula_sum            'C24 H46 Al4 N2 O2'
_chemical_formula_weight         502.55

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'
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'

_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                   7.3610(9)
_cell_length_b                   10.0951(12)
_cell_length_c                   10.6561(14)
_cell_angle_alpha                103.037(10)
_cell_angle_beta                 95.097(10)
_cell_angle_gamma                96.205(10)
_cell_volume                     761.67(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5427
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      29.3

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.096
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.9564
_exptl_absorpt_correction_T_max  0.9784
_exptl_absorpt_process_details   
;
A face-indexed absorption correction was applied 
using the Tompa method implemented within Stoe X-AREA'
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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  'Stoe IPDS2'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 6.67
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7591
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_sigmaI/netI    0.0817
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         29.16
_reflns_number_total             3999
_reflns_number_gt                2412
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Stoe X-AREA'
_computing_cell_refinement       'Stoe X-AREA'
_computing_data_reduction        'Stoe X-AREA'
_computing_structure_solution    SHELXS-86
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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.

 C-H hydrogen atoms were placed using a riding model. The orientation of 
 methyl groups was refined to obtain the best fit to the observed 
 electron density. 
 The single hydrogen atom located on the nitrogen atom was identified in the
 Fourier difference maps and sited with chemically sensible restraints. 
;




_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)+(0.0516P)²] 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         3999
_refine_ls_number_parameters     154
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0932
_refine_ls_goodness_of_fit_ref   0.859
_refine_ls_restrained_S_all      0.860
_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
Al2 Al 0.17898(7) 0.55704(5) 0.06705(5) 0.02443(14) Uani 1 1 d D . .
C1 C 0.2002(3) -0.4085(2) -0.3638(2) 0.0405(5) Uani 1 1 d . . .
H1A H 0.2890 -0.4489 -0.4192 0.061 Uiso 1 1 calc R . .
H1B H 0.0854 -0.4719 -0.3794 0.061 Uiso 1 1 calc R . .
H1C H 0.2509 -0.3915 -0.2725 0.061 Uiso 1 1 calc R . .
C2 C -0.0940(3) -0.1814(2) -0.3734(2) 0.0392(5) Uani 1 1 d . . .
H2A H -0.1042 -0.0923 -0.3938 0.059 Uiso 1 1 calc R . .
H2B H -0.1110 -0.1748 -0.2821 0.059 Uiso 1 1 calc R . .
H2C H -0.1887 -0.2508 -0.4287 0.059 Uiso 1 1 calc R . .
C3 C 0.2588(3) -0.1929(2) -0.5565(2) 0.0462(6) Uani 1 1 d . . .
H3A H 0.1980 -0.2581 -0.6354 0.069 Uiso 1 1 calc R . .
H3B H 0.3905 -0.2012 -0.5475 0.069 Uiso 1 1 calc R . .
H3C H 0.2419 -0.0994 -0.5620 0.069 Uiso 1 1 calc R . .
O1 O 0.30118(17) -0.09900(12) -0.25733(11) 0.0269(3) Uani 1 1 d . . .
C12 C 0.4982(3) -0.1051(2) -0.2344(2) 0.0389(5) Uani 1 1 d . . .
H12A H 0.5648 -0.0466 -0.2817 0.058 Uiso 1 1 calc R . .
H12B H 0.5225 -0.1999 -0.2646 0.058 Uiso 1 1 calc R . .
H12C H 0.5395 -0.0729 -0.1414 0.058 Uiso 1 1 calc R . .
C6 C 0.2522(2) 0.03495(17) -0.21492(16) 0.0247(3) Uani 1 1 d . . .
C7 C 0.2739(3) 0.12667(18) -0.29239(17) 0.0280(4) Uani 1 1 d . . .
H7 H 0.3257 0.1024 -0.3716 0.034 Uiso 1 1 calc R . .
C8 C 0.2184(3) 0.25529(18) -0.25231(17) 0.0276(4) Uani 1 1 d . . .
H8 H 0.2331 0.3195 -0.3047 0.033 Uiso 1 1 calc R . .
C9 C 0.1417(2) 0.29173(17) -0.13680(16) 0.0234(3) Uani 1 1 d . . .
C10 C 0.1246(2) 0.19698(18) -0.05915(16) 0.0264(4) Uani 1 1 d . . .
H10 H 0.0746 0.2206 0.0208 0.032 Uiso 1 1 calc R . .
C11 C 0.1809(2) 0.06822(18) -0.09899(16) 0.0260(4) Uani 1 1 d . . .
H11 H 0.1700 0.0040 -0.0463 0.031 Uiso 1 1 calc R . .
N1 N 0.0792(2) 0.42373(14) -0.09828(13) 0.0236(3) Uani 1 1 d D . .
Al1 Al 0.15016(8) -0.23351(6) -0.40444(5) 0.02762(14) Uani 1 1 d . . .
C4 C 0.3009(3) 0.4690(2) 0.19119(19) 0.0390(5) Uani 1 1 d . . .
H4A H 0.3909 0.4146 0.1493 0.058 Uiso 1 1 calc R . .
H4B H 0.2089 0.4088 0.2206 0.058 Uiso 1 1 calc R . .
H4C H 0.3638 0.5394 0.2658 0.058 Uiso 1 1 calc R . .
C5 C 0.3041(3) 0.72366(19) 0.03156(19) 0.0351(4) Uani 1 1 d . . .
H5A H 0.2871 0.8034 0.0993 0.053 Uiso 1 1 calc R . .
H5B H 0.2521 0.7343 -0.0529 0.053 Uiso 1 1 calc R . .
H5C H 0.4357 0.7166 0.0305 0.053 Uiso 1 1 calc R . .
H1 H 0.102(2) 0.466(2) -0.1586(16) 0.042 Uiso 1 1 d 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
Al2 C5 1.9582(19) . ?
Al2 C4 1.959(2) . ?
Al2 N1 1.9809(15) 2_565 ?
Al2 N1 1.9851(16) . ?
C1 Al1 1.975(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 Al1 1.962(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 Al1 1.973(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
O1 C6 1.422(2) . ?
O1 C12 1.459(2) . ?
O1 Al1 1.9851(14) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C6 C11 1.371(2) . ?
C6 C7 1.379(2) . ?
C7 C8 1.389(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.402(2) . ?
C9 N1 1.440(2) . ?
C10 C11 1.393(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
N1 Al2 1.9809(15) 2_565 ?
N1 H1 0.867(15) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?

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
C5 Al2 C4 119.69(9) . . ?
C5 Al2 N1 111.54(7) . 2_565 ?
C4 Al2 N1 111.68(8) . 2_565 ?
C5 Al2 N1 110.06(8) . . ?
C4 Al2 N1 112.02(8) . . ?
N1 Al2 N1 87.24(6) 2_565 . ?
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 109.5 . . ?
Al1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
Al1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
Al1 C3 H3A 109.5 . . ?
Al1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
Al1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C6 O1 C12 113.54(14) . . ?
C6 O1 Al1 120.28(10) . . ?
C12 O1 Al1 119.52(11) . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C6 C7 121.85(16) . . ?
C11 C6 O1 118.86(15) . . ?
C7 C6 O1 119.28(14) . . ?
C6 C7 C8 118.69(15) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
C7 C8 C9 121.16(15) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C10 118.71(15) . . ?
C8 C9 N1 120.67(14) . . ?
C10 C9 N1 120.62(14) . . ?
C11 C10 C9 120.17(15) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C6 C11 C10 119.41(15) . . ?
C6 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C9 N1 Al2 122.13(11) . 2_565 ?
C9 N1 Al2 122.38(11) . . ?
Al2 N1 Al2 92.76(6) 2_565 . ?
C9 N1 H1 106.2(15) . . ?
Al2 N1 H1 106.3(12) 2_565 . ?
Al2 N1 H1 105.2(12) . . ?
C2 Al1 C3 118.46(10) . . ?
C2 Al1 C1 115.59(10) . . ?
C3 Al1 C1 115.19(10) . . ?
C2 Al1 O1 99.36(8) . . ?
C3 Al1 O1 102.71(8) . . ?
C1 Al1 O1 101.08(8) . . ?
Al2 C4 H4A 109.5 . . ?
Al2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
Al2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Al2 C5 H5A 109.5 . . ?
Al2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
Al2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 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
C12 O1 C6 C11 -100.72(19) . . . . ?
Al1 O1 C6 C11 108.03(16) . . . . ?
C12 O1 C6 C7 80.6(2) . . . . ?
Al1 O1 C6 C7 -70.61(19) . . . . ?
C11 C6 C7 C8 -1.2(3) . . . . ?
O1 C6 C7 C8 177.38(17) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C7 C8 C9 C10 1.4(3) . . . . ?
C7 C8 C9 N1 -177.99(17) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
N1 C9 C10 C11 178.26(17) . . . . ?
C7 C6 C11 C10 1.5(3) . . . . ?
O1 C6 C11 C10 -177.12(16) . . . . ?
C9 C10 C11 C6 -0.3(3) . . . . ?
C8 C9 N1 Al2 121.14(16) . . . 2_565 ?
C10 C9 N1 Al2 -58.2(2) . . . 2_565 ?
C8 C9 N1 Al2 -121.12(16) . . . . ?
C10 C9 N1 Al2 59.5(2) . . . . ?
C5 Al2 N1 C9 116.67(14) . . . . ?
C4 Al2 N1 C9 -19.08(15) . . . . ?
N1 Al2 N1 C9 -131.38(14) 2_565 . . . ?
C5 Al2 N1 Al2 -111.95(8) . . . 2_565 ?
C4 Al2 N1 Al2 112.30(9) . . . 2_565 ?
N1 Al2 N1 Al2 0.0 2_565 . . 2_565 ?
C6 O1 Al1 C2 -34.88(13) . . . . ?
C12 O1 Al1 C2 175.57(13) . . . . ?
C6 O1 Al1 C3 87.29(13) . . . . ?
C12 O1 Al1 C3 -62.26(14) . . . . ?
C6 O1 Al1 C1 -153.45(12) . . . . ?
C12 O1 Al1 C1 57.00(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        25.30
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.055

_database_code_depnum_ccdc_archive 'CCDC 986715'
#######################################################################
#
#                 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_cr38

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H38 Al4 N2 O2'
_chemical_formula_sum            'C22 H38 Al4 N2 O2'
_chemical_formula_weight         470.46

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.7510(7)
_cell_length_b                   15.3173(12)
_cell_length_c                   10.1026(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.1329(13)
_cell_angle_gamma                90
_cell_volume                     1354.17(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6528
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.79

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.192
_shelx_estimated_absorpt_T_min   0.892
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   'SADABS v2.01, Sheldrick, G.M., (2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11499
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.415
_diffrn_reflns_theta_max         28.879
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3228
_reflns_number_gt                2703
_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 SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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)+(0.0520P)²+0.3059P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         3228
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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_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 1.08048(5) 0.06059(3) 0.42625(4) 0.02465(12) Uani 1 1 d . . . . .
C1 C 1.29966(19) 0.07116(12) 0.38918(18) 0.0455(4) Uani 1 1 d . . . . .
H1A H 1.3425 0.1194 0.4410 0.068 Uiso 1 1 calc R U . . .
H1B H 1.3146 0.0826 0.2947 0.068 Uiso 1 1 calc R U . . .
H1C H 1.3514 0.0167 0.4134 0.068 Uiso 1 1 calc R U . . .
C2 C 0.9618(2) 0.15396(10) 0.33853(15) 0.0406(4) Uani 1 1 d . . . . .
H2A H 0.8560 0.1524 0.3700 0.061 Uiso 1 1 calc R U . . .
H2B H 0.9634 0.1450 0.2425 0.061 Uiso 1 1 calc R U . . .
H2C H 1.0072 0.2108 0.3596 0.061 Uiso 1 1 calc R U . . .
Al2 Al 0.89498(4) 0.15546(3) 0.64521(4) 0.02493(12) Uani 1 1 d . . . . .
C3 C 0.67643(18) 0.16515(12) 0.61058(19) 0.0449(4) Uani 1 1 d . . . . .
H3A H 0.6540 0.1432 0.5215 0.067 Uiso 1 1 calc R U . . .
H3B H 0.6454 0.2265 0.6169 0.067 Uiso 1 1 calc R U . . .
H3C H 0.6200 0.1306 0.6759 0.067 Uiso 1 1 calc R U . . .
C4 C 1.02308(19) 0.26028(10) 0.64616(16) 0.0386(4) Uani 1 1 d . . . . .
H4A H 1.1310 0.2432 0.6460 0.058 Uiso 1 1 calc R U . . .
H4B H 1.0014 0.2947 0.7257 0.058 Uiso 1 1 calc R U . . .
H4C H 1.0009 0.2954 0.5673 0.058 Uiso 1 1 calc R U . . .
N1 N 1.01412(12) 0.05318(7) 0.60956(10) 0.0214(2) Uani 1 1 d . . . . .
C5 C 1.11476(15) 0.05089(8) 0.72176(13) 0.0240(3) Uani 1 1 d . . . . .
C6 C 1.26312(17) 0.01775(11) 0.72173(16) 0.0358(3) Uani 1 1 d . . . . .
H6 H 1.3002(19) -0.0065(12) 0.6424(18) 0.041(5) Uiso 1 1 d . . . . .
C7 C 1.3508(2) 0.01877(14) 0.83642(19) 0.0502(4) Uani 1 1 d . . . . .
H7 H 1.458(3) -0.0032(15) 0.835(2) 0.070(7) Uiso 1 1 d . . . . .
C8 C 1.2934(2) 0.05267(13) 0.95245(19) 0.0517(5) Uani 1 1 d . . . . .
H8 H 1.355(3) 0.0550(13) 1.028(2) 0.061(6) Uiso 1 1 d . . . . .
C9 C 1.1461(2) 0.08549(11) 0.95679(16) 0.0401(4) Uani 1 1 d . . . . .
H9 H 1.110(2) 0.1087(12) 1.031(2) 0.044(5) Uiso 1 1 d . . . . .
C10 C 1.06115(16) 0.08400(9) 0.84211(13) 0.0267(3) Uani 1 1 d . . . . .
O1 O 0.91176(11) 0.11744(6) 0.83040(9) 0.0284(2) Uani 1 1 d . . . . .
C11 C 0.8464(2) 0.16334(12) 0.94228(16) 0.0436(4) Uani 1 1 d . . . . .
H11A H 0.8373 0.1233 1.0175 0.065 Uiso 1 1 calc R U . . .
H11B H 0.7450 0.1855 0.9183 0.065 Uiso 1 1 calc R U . . .
H11C H 0.9128 0.2123 0.9668 0.065 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 N1 1.9454(11) . ?
Al1 C1 1.9618(16) . ?
Al1 N1 1.9626(11) 3_756 ?
Al1 C2 1.9759(16) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
Al2 N1 1.9164(11) . ?
Al2 C3 1.9491(16) . ?
Al2 C4 1.9583(16) . ?
Al2 O1 1.9645(10) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N1 C5 1.4343(16) . ?
C5 C6 1.3940(19) . ?
C5 C10 1.3993(19) . ?
C6 C7 1.388(2) . ?
C6 H6 0.942(19) . ?
C7 C8 1.378(3) . ?
C7 H7 1.00(2) . ?
C8 C9 1.384(3) . ?
C8 H8 0.94(2) . ?
C9 C10 1.375(2) . ?
C9 H9 0.89(2) . ?
C10 O1 1.4089(16) . ?
O1 C11 1.4498(16) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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 Al1 C1 118.73(7) . . ?
N1 Al1 N1 89.82(4) . 3_756 ?
C1 Al1 N1 116.76(6) . 3_756 ?
N1 Al1 C2 108.15(6) . . ?
C1 Al1 C2 111.57(8) . . ?
N1 Al1 C2 109.82(6) 3_756 . ?
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 109.5 . . ?
Al1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
Al1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 Al2 C3 124.23(7) . . ?
N1 Al2 C4 111.07(6) . . ?
C3 Al2 C4 119.99(8) . . ?
N1 Al2 O1 84.10(4) . . ?
C3 Al2 O1 105.34(7) . . ?
C4 Al2 O1 101.35(6) . . ?
Al2 C3 H3A 109.5 . . ?
Al2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
Al2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
Al2 C4 H4A 109.5 . . ?
Al2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
Al2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C5 N1 Al2 101.82(8) . . ?
C5 N1 Al1 124.73(8) . . ?
Al2 N1 Al1 107.15(5) . . ?
C5 N1 Al1 112.45(8) . 3_756 ?
Al2 N1 Al1 122.08(6) . 3_756 ?
Al1 N1 Al1 90.18(4) . 3_756 ?
C6 C5 C10 116.51(13) . . ?
C6 C5 N1 125.37(12) . . ?
C10 C5 N1 118.12(11) . . ?
C7 C6 C5 120.57(15) . . ?
C7 C6 H6 121.6(10) . . ?
C5 C6 H6 117.8(10) . . ?
C8 C7 C6 120.84(16) . . ?
C8 C7 H7 119.1(13) . . ?
C6 C7 H7 120.0(13) . . ?
C7 C8 C9 120.32(15) . . ?
C7 C8 H8 120.0(14) . . ?
C9 C8 H8 119.7(13) . . ?
C10 C9 C8 117.97(15) . . ?
C10 C9 H9 121.5(12) . . ?
C8 C9 H9 120.5(12) . . ?
C9 C10 C5 123.79(14) . . ?
C9 C10 O1 124.37(13) . . ?
C5 C10 O1 111.82(11) . . ?
C10 O1 C11 118.59(12) . . ?
C10 O1 Al2 104.78(8) . . ?
C11 O1 Al2 124.75(9) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
Al2 N1 C5 C6 -149.30(13) . . . . ?
Al1 N1 C5 C6 -28.53(18) . . . . ?
Al1 N1 C5 C6 78.35(15) 3_756 . . . ?
Al2 N1 C5 C10 31.04(13) . . . . ?
Al1 N1 C5 C10 151.81(10) . . . . ?
Al1 N1 C5 C10 -101.30(12) 3_756 . . . ?
C10 C5 C6 C7 -0.3(2) . . . . ?
N1 C5 C6 C7 -179.98(15) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C6 C7 C8 C9 0.7(3) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C8 C9 C10 C5 0.3(2) . . . . ?
C8 C9 C10 O1 -177.97(15) . . . . ?
C6 C5 C10 C9 0.2(2) . . . . ?
N1 C5 C10 C9 179.93(13) . . . . ?
C6 C5 C10 O1 178.71(12) . . . . ?
N1 C5 C10 O1 -1.60(17) . . . . ?
C9 C10 O1 C11 5.6(2) . . . . ?
C5 C10 O1 C11 -172.89(12) . . . . ?
C9 C10 O1 Al2 150.16(13) . . . . ?
C5 C10 O1 Al2 -28.30(13) . . . . ?

_refine_diff_density_max         0.310
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-4

_iucr_refine_instruction_details 
; 
TITL cr38 in P2(1)/n 
CELL 0.71073   8.7510  15.3173  10.1026  90.000  90.1329  90.000 
ZERR    2.00   0.0007   0.0012   0.0008   0.000   0.0013   0.000 
LATT  1 
SYMM 0.5-X, 0.5+Y, 0.5-Z 
SFAC C H N O AL 
UNIT 44 76 4 4 8 
TEMP -123 
SIZE 0.09 0.30 0.61 
  
ACTA 
CONF 
WPDB -1 
  
L.S. 6 
BOND $H 
FMAP 2 
PLAN 10 
LIST 4 
  
REM   EXTI    0.000000  INSIGNIFICANT 
WGHT    0.052000    0.305900 
FVAR       0.95456 
AL1   5    1.080475    0.060595    0.426246    11.00000    0.02940    0.02504 = 
         0.01951   -0.00198    0.00462   -0.00429 
C1    1    1.299656    0.071160    0.389177    11.00000    0.03919    0.05096 = 
         0.04631   -0.00757    0.01605   -0.01635 
AFIX 137 
H1A   2    1.342497    0.119447    0.440961    11.00000   -1.50000 
H1B   2    1.314578    0.082620    0.294650    11.00000   -1.50000 
H1C   2    1.351382    0.016689    0.413402    11.00000   -1.50000 
AFIX   0 
C2    1    0.961825    0.153964    0.338533    11.00000    0.06597    0.03036 = 
         0.02544    0.00340   -0.00202    0.00016 
AFIX 137 
H2A   2    0.856007    0.152444    0.369987    11.00000   -1.50000 
H2B   2    0.963427    0.144957    0.242508    11.00000   -1.50000 
H2C   2    1.007197    0.210798    0.359602    11.00000   -1.50000 
AFIX   0 
AL2   5    0.894983    0.155456    0.645209    11.00000    0.02541    0.02523 = 
         0.02417   -0.00080    0.00085    0.00402 
C3    1    0.676432    0.165151    0.610582    11.00000    0.03142    0.04880 = 
         0.05434   -0.00044   -0.00491    0.01111 
AFIX 137 
H3A   2    0.653965    0.143211    0.521516    11.00000   -1.50000 
H3B   2    0.645397    0.226482    0.616884    11.00000   -1.50000 
H3C   2    0.620048    0.130636    0.675936    11.00000   -1.50000 
AFIX   0 
C4    1    1.023085    0.260283    0.646159    11.00000    0.04814    0.02708 = 
         0.04063   -0.00133    0.00777   -0.00129 
AFIX 137 
H4A   2    1.131025    0.243241    0.645967    11.00000   -1.50000 
H4B   2    1.001411    0.294710    0.725696    11.00000   -1.50000 
H4C   2    1.000925    0.295359    0.567290    11.00000   -1.50000 
AFIX   0 
N1    3    1.014118    0.053181    0.609558    11.00000    0.02274    0.02357 = 
         0.01792   -0.00183    0.00002    0.00074 
C5    1    1.114764    0.050893    0.721762    11.00000    0.02558    0.02366 = 
         0.02284   -0.00073   -0.00198   -0.00031 
C6    1    1.263122    0.017748    0.721733    11.00000    0.02942    0.04197 = 
         0.03604   -0.00052   -0.00239    0.00774 
H6    2    1.300198   -0.006479    0.642377    11.00000    0.04116 
C7    1    1.350785    0.018771    0.836425    11.00000    0.03448    0.06279 = 
         0.05312    0.00254   -0.01487    0.01100 
H7    2    1.458499   -0.003178    0.834736    11.00000    0.06999 
C8    1    1.293424    0.052671    0.952450    11.00000    0.05392    0.05859 = 
         0.04236   -0.00036   -0.02643    0.00493 
H8    2    1.355199    0.055028    1.028324    11.00000    0.06140 
C9    1    1.146129    0.085489    0.956787    11.00000    0.05652    0.03982 = 
         0.02386   -0.00531   -0.00871    0.00235 
H9    2    1.109764    0.108683    1.030974    11.00000    0.04407 
C10   1    1.061152    0.083997    0.842109    11.00000    0.03127    0.02482 = 
         0.02412   -0.00138   -0.00274    0.00106 
O1    4    0.911759    0.117444    0.830395    11.00000    0.03226    0.03182 = 
         0.02125   -0.00404    0.00479    0.00650 
C11   1    0.846406    0.163343    0.942280    11.00000    0.05585    0.04720 = 
         0.02784   -0.00903    0.01236    0.01246 
AFIX 137 
H11A  2    0.837286    0.123258    1.017453    11.00000   -1.50000 
H11B  2    0.744997    0.185479    0.918259    11.00000   -1.50000 
H11C  2    0.912762    0.212318    0.966756    11.00000   -1.50000 
AFIX   0 
HKLF 4 
  
REM  cr38 in P2(1)/n 
REM R1 =  0.0329 for    2703 Fo > 4sig(Fo)  and  0.0416 for all    3228 data 
REM    157 parameters refined using      0 restraints 
  
END 
  
WGHT      0.0520      0.3059 
  
REM Highest difference peak  0.310,  deepest hole -0.222,  1-sigma level  0.046 
Q1    1   0.9435  0.0938  0.6209  11.00000  0.05    0.31 
Q2    1   0.9685  0.2111  0.6519  11.00000  0.05    0.30 
Q3    1   1.0168  0.1136  0.3849  11.00000  0.05    0.29 
Q4    1   0.7830  0.1536  0.6228  11.00000  0.05    0.28 
Q5    1   0.9912  0.0970  0.8399  11.00000  0.05    0.28 
Q6    1   0.9665  0.0127  0.6045  11.00000  0.05    0.28 
Q7    1   1.0833  0.0625  0.7852  11.00000  0.05    0.27 
Q8    1   1.1793  0.0342  0.7218  11.00000  0.05    0.25 
Q9    1   1.1059  0.0723  0.9010  11.00000  0.05    0.24 
Q10   1   1.0582  0.0504  0.6605  11.00000  0.05    0.24 
;

_database_code_depnum_ccdc_archive 'CCDC 986716'
#######################################################################
#
#                 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_cr42


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H46 Al4 N2 O2, C7 H8'
_chemical_formula_sum            'C31 H54 Al4 N2 O2'
_chemical_formula_weight         594.68

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.1092(4)
_cell_length_b                   21.2450(12)
_cell_length_c                   12.3300(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.839(2)
_cell_angle_gamma                90
_cell_volume                     1859.98(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6768
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      28.40

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.062
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.730
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.152
_shelx_estimated_absorpt_T_min   0.897
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'SADABS v2.01, Sheldrick, G.M., (2000)'

_exptl_special_details           ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15849
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.917
_diffrn_reflns_theta_max         28.693
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4408
_reflns_number_gt                3463
_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 SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXs-97 (Sheldrick, 2008)'
_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)+(0.0486P)²+0.7440P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4408
_refine_ls_number_parameters     235
_refine_ls_number_restraints     52
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1073
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.054
_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 0.10328(7) 0.23031(2) 0.24514(4) 0.03661(14) Uani 1 1 d . . . . .
C1 C 0.0038(4) 0.20683(19) 0.0999(2) 0.1045(12) Uani 1 1 d . . . . .
H1A H -0.0591 0.2432 0.0653 0.157 Uiso 1 1 calc R U . . .
H1B H -0.0867 0.1724 0.1056 0.157 Uiso 1 1 calc R U . . .
H1C H 0.1075 0.1932 0.0560 0.157 Uiso 1 1 calc R U . . .
C2 C 0.2618(3) 0.16702(9) 0.3221(2) 0.0657(6) Uani 1 1 d . . . . .
H2A H 0.3396 0.1454 0.2702 0.099 Uiso 1 1 calc R U . . .
H2B H 0.1814 0.1363 0.3569 0.099 Uiso 1 1 calc R U . . .
H2C H 0.3434 0.1878 0.3776 0.099 Uiso 1 1 calc R U . . .
C3 C -0.0613(3) 0.27828(9) 0.33687(16) 0.0502(5) Uani 1 1 d . . . . .
H3A H 0.0100 0.2919 0.4028 0.075 Uiso 1 1 calc R U . . .
H3B H -0.1670 0.2518 0.3568 0.075 Uiso 1 1 calc R U . . .
H3C H -0.1096 0.3153 0.2970 0.075 Uiso 1 1 calc R U . . .
Al2 Al -0.16176(6) 0.50037(2) 0.06428(4) 0.02861(12) Uani 1 1 d . . . . .
C4 C -0.2646(2) 0.42041(8) 0.11129(14) 0.0415(4) Uani 1 1 d . . . . .
H4A H -0.2262 0.4131 0.1877 0.062 Uiso 1 1 calc R U . . .
H4B H -0.2170 0.3863 0.0668 0.062 Uiso 1 1 calc R U . . .
H4C H -0.4024 0.4217 0.1031 0.062 Uiso 1 1 calc R U . . .
C5 C -0.2780(3) 0.57926(9) 0.10839(14) 0.0489(5) Uani 1 1 d . . . . .
H5A H -0.3871 0.5886 0.0593 0.073 Uiso 1 1 calc R U . . .
H5B H -0.1862 0.6135 0.1052 0.073 Uiso 1 1 calc R U . . .
H5C H -0.3190 0.5752 0.1828 0.073 Uiso 1 1 calc R U . . .
O1 O 0.29435(16) 0.29244(5) 0.20935(10) 0.0393(3) Uani 1 1 d . . . . .
C6 C 0.28894(19) 0.35790(6) 0.23110(12) 0.0284(3) Uani 1 1 d . . . . .
C7 C 0.3731(2) 0.37992(8) 0.32619(13) 0.0368(4) Uani 1 1 d . . . . .
H7 H 0.430(3) 0.3531(10) 0.3743(17) 0.058(6) Uiso 1 1 d . . . . .
C8 C 0.3700(2) 0.44410(8) 0.34407(12) 0.0370(4) Uani 1 1 d . . . . .
H8 H 0.423(3) 0.4610(9) 0.4092(16) 0.048(5) Uiso 1 1 d . . . . .
C9 C 0.2873(2) 0.48476(7) 0.26802(12) 0.0291(3) Uani 1 1 d . . . . .
H9 H 0.286(2) 0.5283(8) 0.2814(14) 0.034(4) Uiso 1 1 d . . . . .
C10 C 0.20219(17) 0.46144(6) 0.17198(10) 0.0220(3) Uani 1 1 d . . . . .
C11 C 0.20196(19) 0.39665(6) 0.15402(11) 0.0241(3) Uani 1 1 d . . . . .
H11 H 0.148(2) 0.3801(8) 0.0914(14) 0.033(4) Uiso 1 1 d . . . . .
C12 C 0.4534(3) 0.27389(8) 0.14719(19) 0.0551(5) Uani 1 1 d . . . . .
H12A H 0.4446 0.2946 0.0761 0.083 Uiso 1 1 calc R U . . .
H12B H 0.4520 0.2281 0.1371 0.083 Uiso 1 1 calc R U . . .
H12C H 0.5708 0.2864 0.1863 0.083 Uiso 1 1 calc R U . . .
N1 N 0.11473(16) 0.50315(5) 0.09261(10) 0.0247(2) Uani 1 1 d . . . . .
H1 H 0.139(3) 0.5401(9) 0.1111(14) 0.036(5) Uiso 1 1 d . . . . .
C13 C 0.0205(6) 0.4644(2) 0.5270(3) 0.0517(9) Uani 0.5 1 d D U P A -1
C14 C -0.1146(14) 0.4629(4) 0.4467(8) 0.0459(15) Uani 0.5 1 d D U P A -1
H14 H -0.1782 0.4247 0.4284 0.055 Uiso 0.5 1 calc R U P A -1
C15 C -0.1607(7) 0.5198(2) 0.3896(4) 0.0637(11) Uani 0.5 1 d D U P A -1
H15 H -0.2569 0.5199 0.3333 0.076 Uiso 0.5 1 calc R U P A -1
C16 C -0.0679(13) 0.5731(3) 0.4155(9) 0.085(2) Uani 0.5 1 d D U P A -1
H16 H -0.0991 0.6105 0.3765 0.101 Uiso 0.5 1 calc R U P A -1
C17 C 0.0698(10) 0.5749(3) 0.4962(6) 0.0910(18) Uani 0.5 1 d D U P A -1
H17 H 0.1353 0.6129 0.5132 0.109 Uiso 0.5 1 calc R U P A -1
C18 C 0.1138(16) 0.5178(4) 0.5552(10) 0.067(2) Uani 0.5 1 d D U P A -1
H18 H 0.2070 0.5177 0.6132 0.080 Uiso 0.5 1 calc R U P A -1
C19 C 0.0676(16) 0.4033(4) 0.5835(8) 0.103(3) Uani 0.5 1 d D U P A -1
H19A H -0.0476 0.3845 0.6097 0.155 Uiso 0.5 1 calc R U P A -1
H19B H 0.1568 0.4112 0.6452 0.155 Uiso 0.5 1 calc R U P A -1
H19C H 0.1244 0.3743 0.5326 0.155 Uiso 0.5 1 calc R U P A -1


_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 C3 1.9541(19) . ?
Al1 C1 1.957(2) . ?
Al1 O1 1.9600(11) . ?
Al1 C2 1.968(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
Al2 C4 1.9490(16) . ?
Al2 C5 1.9577(18) . ?
Al2 N1 1.9802(12) . ?
Al2 N1 1.9807(13) 3_565 ?
Al2 Al2 2.8573(8) 3_565 ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
O1 C6 1.4173(17) . ?
O1 C12 1.451(2) . ?
C6 C7 1.372(2) . ?
C6 C11 1.3803(19) . ?
C7 C8 1.382(2) . ?
C7 H7 0.90(2) . ?
C8 C9 1.384(2) . ?
C8 H8 0.94(2) . ?
C9 C10 1.3938(19) . ?
C9 H9 0.940(17) . ?
C10 C11 1.3941(18) . ?
C10 N1 1.4385(16) . ?
C11 H11 0.916(17) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N1 Al2 1.9807(13) 3_565 ?
N1 H1 0.833(19) . ?
C13 C14 1.344(9) . ?
C13 C18 1.351(8) . ?
C13 C19 1.503(8) . ?
C14 C15 1.430(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.340(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.362(11) . ?
C16 H16 0.9500 . ?
C17 C18 1.441(11) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C3 Al1 C1 117.58(12) . . ?
C3 Al1 O1 102.74(7) . . ?
C1 Al1 O1 100.87(10) . . ?
C3 Al1 C2 114.98(9) . . ?
C1 Al1 C2 116.07(15) . . ?
O1 Al1 C2 100.48(7) . . ?
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 109.5 . . ?
Al1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
Al1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
Al1 C3 H3A 109.5 . . ?
Al1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
Al1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 Al2 C5 119.59(9) . . ?
C4 Al2 N1 110.93(6) . . ?
C5 Al2 N1 110.76(7) . . ?
C4 Al2 N1 109.97(7) . 3_565 ?
C5 Al2 N1 113.43(6) . 3_565 ?
N1 Al2 N1 87.67(5) . 3_565 ?
C4 Al2 Al2 118.97(6) . 3_565 ?
C5 Al2 Al2 121.42(7) . 3_565 ?
N1 Al2 Al2 43.84(4) . 3_565 ?
N1 Al2 Al2 43.83(4) 3_565 3_565 ?
Al2 C4 H4A 109.5 . . ?
Al2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
Al2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Al2 C5 H5A 109.5 . . ?
Al2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
Al2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C6 O1 C12 113.30(11) . . ?
C6 O1 Al1 126.35(9) . . ?
C12 O1 Al1 120.17(10) . . ?
C7 C6 C11 123.14(14) . . ?
C7 C6 O1 118.79(13) . . ?
C11 C6 O1 118.06(13) . . ?
C6 C7 C8 117.59(14) . . ?
C6 C7 H7 120.6(14) . . ?
C8 C7 H7 121.8(14) . . ?
C7 C8 C9 121.16(14) . . ?
C7 C8 H8 120.2(12) . . ?
C9 C8 H8 118.6(12) . . ?
C8 C9 C10 120.37(14) . . ?
C8 C9 H9 120.1(11) . . ?
C10 C9 H9 119.5(11) . . ?
C9 C10 C11 118.88(12) . . ?
C9 C10 N1 120.92(12) . . ?
C11 C10 N1 120.20(12) . . ?
C6 C11 C10 118.85(13) . . ?
C6 C11 H11 120.5(10) . . ?
C10 C11 H11 120.6(10) . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 N1 Al2 119.57(9) . . ?
C10 N1 Al2 123.58(9) . 3_565 ?
Al2 N1 Al2 92.33(5) . 3_565 ?
C10 N1 H1 108.4(12) . . ?
Al2 N1 H1 105.6(12) . . ?
Al2 N1 H1 105.1(12) 3_565 . ?
C14 C13 C18 122.2(7) . . ?
C14 C13 C19 117.1(6) . . ?
C18 C13 C19 120.7(7) . . ?
C13 C14 C15 118.7(6) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C14 119.9(7) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 121.7(8) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C16 C17 C18 118.4(7) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C13 C18 C17 119.0(9) . . ?
C13 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C12 O1 C6 C7 -92.52(18) . . . . ?
Al1 O1 C6 C7 92.40(15) . . . . ?
C12 O1 C6 C11 86.21(18) . . . . ?
Al1 O1 C6 C11 -88.88(15) . . . . ?
C11 C6 C7 C8 -0.3(2) . . . . ?
O1 C6 C7 C8 178.37(13) . . . . ?
C6 C7 C8 C9 -0.9(2) . . . . ?
C7 C8 C9 C10 1.1(2) . . . . ?
C8 C9 C10 C11 0.0(2) . . . . ?
C8 C9 C10 N1 179.60(13) . . . . ?
C7 C6 C11 C10 1.3(2) . . . . ?
O1 C6 C11 C10 -177.35(11) . . . . ?
C9 C10 C11 C6 -1.12(19) . . . . ?
N1 C10 C11 C6 179.25(12) . . . . ?
C9 C10 N1 Al2 -113.06(13) . . . . ?
C11 C10 N1 Al2 66.56(15) . . . . ?
C9 C10 N1 Al2 131.30(12) . . . 3_565 ?
C11 C10 N1 Al2 -49.08(16) . . . 3_565 ?
C18 C13 C14 C15 0.0(18) . . . . ?
C19 C13 C14 C15 -178.8(8) . . . . ?
C13 C14 C15 C16 0.9(13) . . . . ?
C14 C15 C16 C17 -0.5(13) . . . . ?
C15 C16 C17 C18 -0.6(13) . . . . ?
C14 C13 C18 C17 -1.2(18) . . . . ?
C19 C13 C18 C17 177.6(8) . . . . ?
C16 C17 C18 C13 1.5(14) . . . . ?

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-4




_database_code_depnum_ccdc_archive 'CCDC 986717'
