# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013


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#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
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#  as required by the journal to which it was submitted. 
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data_trial1
_database_code_depnum_ccdc_archive 'CCDC 888916'
#TrackingRef 'CIF.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24.33 H25.33 Al N3 O6'
_chemical_formula_weight         482.79
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'
_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'
_cell_length_a                   15.1430(4)
_cell_length_b                   13.8141(4)
_cell_length_c                   17.0179(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3559.92(17)
_cell_formula_units_Z            6
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1520
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34767
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         27.11
_reflns_number_total             3918
_reflns_number_gt                2982
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1573P)^2^+2.6779P] where P=(Fo^2^+2Fc^2^)/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         3918
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1561
_refine_ls_wR_factor_gt          0.1237
_refine_ls_goodness_of_fit_ref   0.627
_refine_ls_restrained_S_all      0.627
_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
O1 O 0.68564(8) 0.46315(7) 0.13506(7) 0.0459(3) Uani 1 1 d . . .
O2 O 0.52673(9) 0.35796(9) 0.01008(8) 0.0561(4) Uani 1 1 d . . .
O3 O 0.69749(10) 0.18700(10) -0.02346(9) 0.0675(4) Uani 1 1 d . . .
O4 O 0.51688(11) 0.22465(11) 0.18691(9) 0.0699(4) Uani 1 1 d . . .
C24 C 0.49831(14) -0.13430(15) 0.14058(12) 0.0558(5) Uani 1 1 d . . .
C27 C 0.53145(10) 0.06369(11) 0.13922(9) 0.0394(3) Uani 1 1 d . . .
N3 N 0.60851(10) 0.20195(9) 0.08317(9) 0.0447(3) Uani 1 1 d . . .
N4 N 0.79706(9) 0.44172(9) 0.25342(9) 0.0449(3) Uani 1 1 d . . .
C26 C 0.45892(14) -0.07544(17) 0.19443(13) 0.0609(5) Uani 1 1 d . . .
C25 C 0.47533(13) 0.02402(16) 0.19401(11) 0.0537(5) Uani 1 1 d . . .
C1 C 0.55594(11) -0.09674(11) 0.08273(10) 0.0420(4) Uani 1 1 d . . .
C2 C 0.57293(10) 0.00456(10) 0.08244(8) 0.0349(3) Uani 1 1 d . . .
C3 C 0.54885(11) 0.16843(12) 0.14058(10) 0.0452(4) Uani 1 1 d . . .
N6 N 0.63347(11) 0.29832(10) 0.08980(10) 0.0530(4) Uani 1 1 d . . .
H4 H 0.6794 0.3127 0.1172 0.064 Uiso 1 1 calc R . .
C5 C 0.58833(11) 0.36932(11) 0.05500(9) 0.0406(4) Uani 1 1 d . . .
C6 C 0.62067(11) 0.46951(11) 0.07563(10) 0.0440(4) Uani 1 1 d . . .
H6C H 0.6455 0.5002 0.0294 0.053 Uiso 1 1 calc R . .
H6D H 0.5716 0.5087 0.0939 0.053 Uiso 1 1 calc R . .
C7 C 0.70856(10) 0.54624(10) 0.17379(9) 0.0367(3) Uani 1 1 d . . .
C8 C 0.76799(10) 0.53269(10) 0.23757(9) 0.0356(3) Uani 1 1 d . . .
C9 C 0.85270(12) 0.43165(14) 0.31254(11) 0.0512(4) Uani 1 1 d . . .
H9 H 0.8736 0.3699 0.3237 0.061 Uiso 1 1 calc R . .
C10 C 0.88219(12) 0.50846(15) 0.35960(11) 0.0514(4) Uani 1 1 d . . .
H10 H 0.9212 0.4972 0.4008 0.062 Uiso 1 1 calc R . .
C11 C 0.67763(12) 0.63661(11) 0.15502(10) 0.0437(4) Uani 1 1 d . . .
H11 H 0.6398 0.6447 0.1125 0.052 Uiso 1 1 calc R . .
C12 C 0.70333(12) 0.71722(12) 0.20029(11) 0.0492(4) Uani 1 1 d . . .
H12 H 0.6813 0.7781 0.1878 0.059 Uiso 1 1 calc R . .
C13 C 0.75988(12) 0.70744(11) 0.26197(11) 0.0482(4) Uani 1 1 d . . .
H13 H 0.7762 0.7614 0.2912 0.058 Uiso 1 1 calc R . .
C14 C 0.79387(10) 0.61494(11) 0.28167(10) 0.0407(4) Uani 1 1 d . . .
C15 C 0.85303(12) 0.59959(13) 0.34428(10) 0.0486(4) Uani 1 1 d . . .
H15 H 0.8720 0.6514 0.3749 0.058 Uiso 1 1 calc R . .
C16 C 0.59742(12) -0.15500(12) 0.02549(12) 0.0518(5) Uani 1 1 d . . .
H16 H 0.5871 -0.2214 0.0252 0.062 Uiso 1 1 calc R . .
C17 C 0.65221(13) -0.11574(14) -0.02920(12) 0.0546(5) Uani 1 1 d . . .
H17 H 0.6792 -0.1555 -0.0662 0.066 Uiso 1 1 calc R . .
C18 C 0.66837(11) -0.01599(13) -0.03025(11) 0.0471(4) Uani 1 1 d . . .
H18 H 0.7053 0.0102 -0.0684 0.056 Uiso 1 1 calc R . .
C19 C 0.62994(10) 0.04335(11) 0.02475(9) 0.0372(3) Uani 1 1 d . . .
C20 C 0.64955(11) 0.14785(12) 0.02367(10) 0.0430(4) Uani 1 1 d . . .
H19 H 0.4896(15) -0.2023(17) 0.1415(13) 0.063(6) Uiso 1 1 d . . .
H20 H 0.4476(16) 0.0688(18) 0.2311(15) 0.077(7) Uiso 1 1 d . . .
H21 H 0.4200(17) -0.1003(18) 0.2314(16) 0.083(8) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0571(7) 0.0274(5) 0.0532(7) -0.0063(5) -0.0141(5) -0.0009(5)
O2 0.0601(8) 0.0446(7) 0.0638(8) 0.0017(6) -0.0201(6) -0.0104(6)
O3 0.0770(9) 0.0535(8) 0.0719(9) 0.0033(7) 0.0169(8) -0.0226(7)
O4 0.0818(10) 0.0542(8) 0.0738(10) -0.0229(7) 0.0090(8) 0.0090(7)
C24 0.0601(11) 0.0454(10) 0.0620(11) 0.0159(9) -0.0123(9) -0.0148(8)
C27 0.0398(8) 0.0388(8) 0.0397(8) 0.0002(6) -0.0039(6) 0.0004(6)
N3 0.0512(8) 0.0273(6) 0.0558(8) -0.0024(6) -0.0059(6) -0.0043(6)
N4 0.0518(8) 0.0331(7) 0.0498(8) -0.0010(6) -0.0026(6) 0.0021(6)
C26 0.0601(11) 0.0675(13) 0.0550(11) 0.0185(10) 0.0030(9) -0.0145(10)
C25 0.0527(10) 0.0634(12) 0.0448(10) 0.0037(8) 0.0029(8) -0.0024(9)
C1 0.0449(8) 0.0312(7) 0.0499(9) 0.0047(6) -0.0151(7) -0.0035(6)
C2 0.0354(7) 0.0313(7) 0.0381(7) 0.0017(6) -0.0087(6) -0.0004(6)
C3 0.0476(9) 0.0389(8) 0.0492(9) -0.0056(7) -0.0059(7) 0.0042(7)
N6 0.0591(9) 0.0286(7) 0.0711(10) -0.0030(6) -0.0212(7) -0.0060(6)
C5 0.0451(8) 0.0343(8) 0.0425(8) -0.0017(6) -0.0022(7) -0.0045(6)
C6 0.0473(9) 0.0343(8) 0.0504(9) 0.0003(7) -0.0099(7) -0.0043(6)
C7 0.0424(8) 0.0260(7) 0.0415(8) -0.0036(6) 0.0041(6) -0.0049(6)
C8 0.0379(8) 0.0282(7) 0.0407(8) -0.0025(6) 0.0064(6) -0.0031(5)
C9 0.0535(10) 0.0450(9) 0.0551(11) 0.0023(8) -0.0030(8) 0.0052(8)
C10 0.0442(9) 0.0640(11) 0.0460(9) -0.0011(8) -0.0023(7) 0.0003(8)
C11 0.0504(9) 0.0310(8) 0.0498(9) 0.0020(6) -0.0008(7) -0.0021(7)
C12 0.0589(10) 0.0269(8) 0.0616(11) -0.0016(7) 0.0035(8) 0.0007(7)
C13 0.0570(10) 0.0294(8) 0.0581(10) -0.0121(7) 0.0049(8) -0.0073(7)
C14 0.0420(8) 0.0377(8) 0.0424(8) -0.0069(6) 0.0066(6) -0.0074(6)
C15 0.0498(9) 0.0504(10) 0.0455(9) -0.0108(7) 0.0022(7) -0.0101(7)
C16 0.0622(11) 0.0290(7) 0.0643(11) -0.0044(7) -0.0199(9) 0.0024(7)
C17 0.0592(11) 0.0456(10) 0.0590(11) -0.0151(8) -0.0050(9) 0.0113(8)
C18 0.0418(8) 0.0480(9) 0.0514(9) -0.0050(7) 0.0018(7) 0.0014(7)
C19 0.0344(7) 0.0342(8) 0.0429(8) -0.0012(6) -0.0055(6) -0.0001(6)
C20 0.0434(8) 0.0368(8) 0.0487(9) 0.0020(7) -0.0038(7) -0.0071(6)
_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
O1 C7 1.3683(17) . ?
O1 C6 1.414(2) . ?
O2 C5 1.216(2) . ?
O3 C20 1.209(2) . ?
O4 C3 1.208(2) . ?
C24 C26 1.363(3) . ?
C24 C1 1.414(3) . ?
C24 H19 0.95(2) . ?
C27 C25 1.375(2) . ?
C27 C2 1.413(2) . ?
C27 C3 1.471(2) . ?
N3 N6 1.3885(18) . ?
N3 C20 1.404(2) . ?
N3 C3 1.409(2) . ?
N4 C9 1.320(2) . ?
N4 C8 1.3586(19) . ?
C26 C25 1.396(3) . ?
C26 H21 0.93(3) . ?
C25 H20 0.98(3) . ?
C1 C16 1.411(3) . ?
C1 C2 1.423(2) . ?
C2 C19 1.413(2) . ?
N6 C5 1.334(2) . ?
N6 H4 0.8600 . ?
C5 C6 1.509(2) . ?
C6 H6C 0.9700 . ?
C6 H6D 0.9700 . ?
C7 C11 1.371(2) . ?
C7 C8 1.422(2) . ?
C8 C14 1.417(2) . ?
C9 C10 1.402(3) . ?
C9 H9 0.9300 . ?
C10 C15 1.359(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.409(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.361(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.418(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.408(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.360(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.400(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.474(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
C7 O1 C6 117.98(12) . . ?
C26 C24 C1 121.29(18) . . ?
C26 C24 H19 121.3(14) . . ?
C1 C24 H19 117.4(14) . . ?
C25 C27 C2 120.54(16) . . ?
C25 C27 C3 119.47(16) . . ?
C2 C27 C3 119.98(15) . . ?
N6 N3 C20 116.66(14) . . ?
N6 N3 C3 115.68(14) . . ?
C20 N3 C3 127.53(13) . . ?
C9 N4 C8 117.11(14) . . ?
C24 C26 C25 120.39(18) . . ?
C24 C26 H21 120.8(16) . . ?
C25 C26 H21 118.8(16) . . ?
C27 C25 C26 120.36(19) . . ?
C27 C25 H20 116.8(15) . . ?
C26 C25 H20 122.9(15) . . ?
C16 C1 C24 123.10(16) . . ?
C16 C1 C2 118.55(16) . . ?
C24 C1 C2 118.35(17) . . ?
C27 C2 C19 121.86(14) . . ?
C27 C2 C1 119.07(14) . . ?
C19 C2 C1 119.07(14) . . ?
O4 C3 N3 119.89(16) . . ?
O4 C3 C27 124.81(17) . . ?
N3 C3 C27 115.30(14) . . ?
C5 N6 N3 121.96(14) . . ?
C5 N6 H4 119.0 . . ?
N3 N6 H4 119.0 . . ?
O2 C5 N6 125.25(15) . . ?
O2 C5 C6 120.89(15) . . ?
N6 C5 C6 113.87(14) . . ?
O1 C6 C5 109.59(13) . . ?
O1 C6 H6C 109.8 . . ?
C5 C6 H6C 109.8 . . ?
O1 C6 H6D 109.8 . . ?
C5 C6 H6D 109.8 . . ?
H6C C6 H6D 108.2 . . ?
O1 C7 C11 124.39(15) . . ?
O1 C7 C8 114.69(12) . . ?
C11 C7 C8 120.92(14) . . ?
N4 C8 C14 123.16(15) . . ?
N4 C8 C7 118.57(13) . . ?
C14 C8 C7 118.27(13) . . ?
N4 C9 C10 123.99(17) . . ?
N4 C9 H9 118.0 . . ?
C10 C9 H9 118.0 . . ?
C15 C10 C9 119.19(17) . . ?
C15 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C7 C11 C12 119.86(16) . . ?
C7 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 121.13(15) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 120.01(14) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C8 117.13(15) . . ?
C15 C14 C13 123.06(15) . . ?
C8 C14 C13 119.80(15) . . ?
C10 C15 C14 119.42(16) . . ?
C10 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C1 121.11(16) . . ?
C17 C16 H16 119.4 . . ?
C1 C16 H16 119.4 . . ?
C16 C17 C18 120.54(17) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 120.31(17) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C2 120.41(15) . . ?
C18 C19 C20 119.37(15) . . ?
C2 C19 C20 120.22(14) . . ?
O3 C20 N3 120.40(15) . . ?
O3 C20 C19 124.56(16) . . ?
N3 C20 C19 115.04(14) . . ?
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.11
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.041