# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_uor001

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10.50 H7.50 Al0.50 O3'
_chemical_formula_weight         195.16

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'
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           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

loop_
_symmetry_equiv_pos_as_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                   9.5167(5)
_cell_length_b                   9.9644(3)
_cell_length_c                   19.0736(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.406(4)
_cell_angle_gamma                90.00
_cell_volume                     1778.97(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3024
_cell_measurement_theta_min      2.9763
_cell_measurement_theta_max      32.5269

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_min  0.9516
_exptl_absorpt_correction_T_max  0.9688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13807
_diffrn_reflns_av_R_equivalents  0.0962
_diffrn_reflns_av_sigmaI/netI    0.0821
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3132
_reflns_number_gt                2187
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0527P)²+0.5556P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3132
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1429
_refine_ls_wR_factor_gt          0.1239
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Al1 Al 0.78132(12) 0.26850(8) 0.41891(4) 0.0316(3) Uani 1 1 d . . .
O1 O 0.6316(2) 0.20446(19) 0.35259(10) 0.0337(6) Uani 1 1 d . . .
O2 O 0.7636(2) 0.44550(18) 0.37634(10) 0.0323(5) Uani 1 1 d . . .
O3 O 0.9043(3) 0.21981(19) 0.35869(10) 0.0335(5) Uani 1 1 d . . .
O4 O 0.9440(3) 0.3372(2) 0.48605(10) 0.0372(6) Uani 1 1 d . . .
O5 O 0.8097(3) 0.0977(2) 0.46515(10) 0.0393(6) Uani 1 1 d . . .
O6 O 0.6676(3) 0.32607(19) 0.48113(10) 0.0380(6) Uani 1 1 d . . .
C1 C 0.5995(4) 0.2424(3) 0.28570(15) 0.0292(7) Uani 1 1 d . . .
C2 C 0.5169(4) 0.1612(3) 0.23405(16) 0.0364(8) Uani 1 1 d . . .
H2 H 0.4817 0.0779 0.2479 0.044 Uiso 1 1 calc R . .
C3 C 0.4857(4) 0.1998(3) 0.16383(16) 0.0401(8) Uani 1 1 d . . .
H3 H 0.4300 0.1425 0.1299 0.048 Uiso 1 1 calc R . .
C4 C 0.5348(4) 0.3219(3) 0.14152(16) 0.0408(9) Uani 1 1 d . . .
H4 H 0.5153 0.3459 0.0925 0.049 Uiso 1 1 calc R . .
C5 C 0.6101(4) 0.4058(3) 0.18979(15) 0.0351(8) Uani 1 1 d . . .
H5 H 0.6397 0.4904 0.1747 0.042 Uiso 1 1 calc R . .
C6 C 0.6457(4) 0.3694(3) 0.26255(15) 0.0290(7) Uani 1 1 d . . .
C7 C 0.7174(4) 0.4634(3) 0.31113(15) 0.0306(7) Uani 1 1 d . . .
H7 H 0.7325 0.5497 0.2926 0.037 Uiso 1 1 calc R . .
C8 C 1.0285(4) 0.2685(3) 0.35304(16) 0.0325(8) Uani 1 1 d . . .
C9 C 1.0846(4) 0.2478(3) 0.29073(17) 0.0434(9) Uani 1 1 d . . .
H9 H 1.0332 0.1945 0.2534 0.052 Uiso 1 1 calc R . .
C10 C 1.2131(5) 0.3037(4) 0.2831(2) 0.0601(11) Uani 1 1 d . . .
H10 H 1.2472 0.2903 0.2398 0.072 Uiso 1 1 calc R . .
C11 C 1.2947(5) 0.3794(4) 0.3370(2) 0.0647(12) Uani 1 1 d . . .
H11 H 1.3827 0.4179 0.3303 0.078 Uiso 1 1 calc R . .
C12 C 1.2466(4) 0.3975(3) 0.39938(19) 0.0481(9) Uani 1 1 d . . .
H12 H 1.3026 0.4468 0.4370 0.058 Uiso 1 1 calc R . .
C13 C 1.1140(4) 0.3434(3) 0.40836(16) 0.0344(8) Uani 1 1 d . . .
C14 C 1.0669(4) 0.3650(3) 0.47330(16) 0.0374(8) Uani 1 1 d . . .
H14 H 1.1332 0.4040 0.5110 0.045 Uiso 1 1 calc R . .
C15 C 0.6038(4) 0.2561(3) 0.52531(14) 0.0321(8) Uani 1 1 d . . .
C16 C 0.4982(4) 0.3162(3) 0.55691(15) 0.0374(8) Uani 1 1 d . . .
H16 H 0.4754 0.4082 0.5482 0.045 Uiso 1 1 calc R . .
C17 C 0.4270(4) 0.2427(3) 0.60056(16) 0.0421(9) Uani 1 1 d . . .
H17 H 0.3524 0.2841 0.6198 0.051 Uiso 1 1 calc R . .
C18 C 0.4617(4) 0.1078(3) 0.61754(16) 0.0441(9) Uani 1 1 d . . .
H18 H 0.4118 0.0588 0.6481 0.053 Uiso 1 1 calc R . .
C19 C 0.5674(4) 0.0491(3) 0.58966(16) 0.0412(9) Uani 1 1 d . . .
H19 H 0.5930 -0.0412 0.6018 0.049 Uiso 1 1 calc R . .
C20 C 0.6411(4) 0.1199(3) 0.54249(15) 0.0352(8) Uani 1 1 d . . .
C21 C 0.7440(4) 0.0522(3) 0.51177(16) 0.0417(9) Uani 1 1 d . . .
H21 H 0.7664 -0.0369 0.5277 0.050 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Al1 O6 1.836(2) . ?
Al1 O1 1.840(2) . ?
Al1 O3 1.847(2) . ?
Al1 O5 1.914(2) . ?
Al1 O2 1.936(2) . ?
Al1 O4 1.947(3) . ?
O1 C1 1.312(3) . ?
O2 C7 1.255(3) . ?
O3 C8 1.300(4) . ?
O4 C14 1.267(4) . ?
O5 C21 1.260(4) . ?
O6 C15 1.323(3) . ?
C1 C2 1.401(4) . ?
C1 C6 1.435(4) . ?
C2 C3 1.373(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.397(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.350(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.415(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.405(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.403(4) . ?
C8 C13 1.422(5) . ?
C9 C10 1.375(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.362(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.411(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.408(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.396(5) . ?
C15 C20 1.426(4) . ?
C16 C17 1.376(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.408(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.353(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.423(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.401(5) . ?
C21 H21 0.9500 . ?

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
O6 Al1 O1 94.53(11) . . ?
O6 Al1 O3 176.10(11) . . ?
O1 Al1 O3 88.88(10) . . ?
O6 Al1 O5 91.76(9) . . ?
O1 Al1 O5 92.05(10) . . ?
O3 Al1 O5 90.02(10) . . ?
O6 Al1 O2 88.25(9) . . ?
O1 Al1 O2 91.69(10) . . ?
O3 Al1 O2 89.75(9) . . ?
O5 Al1 O2 176.25(11) . . ?
O6 Al1 O4 87.51(10) . . ?
O1 Al1 O4 177.73(10) . . ?
O3 Al1 O4 89.04(10) . . ?
O5 Al1 O4 88.86(10) . . ?
O2 Al1 O4 87.39(9) . . ?
C1 O1 Al1 125.7(2) . . ?
C7 O2 Al1 122.23(18) . . ?
C8 O3 Al1 129.90(19) . . ?
C14 O4 Al1 127.1(2) . . ?
C21 O5 Al1 126.7(2) . . ?
C15 O6 Al1 129.73(19) . . ?
O1 C1 C2 121.3(3) . . ?
O1 C1 C6 121.5(3) . . ?
C2 C1 C6 117.2(3) . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 118.5(3) . . ?
C7 C6 C1 121.6(3) . . ?
C5 C6 C1 119.7(3) . . ?
O2 C7 C6 126.9(3) . . ?
O2 C7 H7 116.5 . . ?
C6 C7 H7 116.5 . . ?
O3 C8 C9 120.4(3) . . ?
O3 C8 C13 122.8(3) . . ?
C9 C8 C13 116.9(3) . . ?
C10 C9 C8 120.7(4) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 122.0(3) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C12 C11 C10 119.1(4) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 120.3(4) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 118.8(3) . . ?
C14 C13 C8 120.2(3) . . ?
C12 C13 C8 121.0(3) . . ?
O4 C14 C13 125.9(3) . . ?
O4 C14 H14 117.0 . . ?
C13 C14 H14 117.0 . . ?
O6 C15 C16 119.9(3) . . ?
O6 C15 C20 121.6(3) . . ?
C16 C15 C20 118.5(3) . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 121.8(3) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C19 C18 C17 118.8(3) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C18 C19 C20 121.4(3) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C21 C20 C19 119.2(3) . . ?
C21 C20 C15 121.7(3) . . ?
C19 C20 C15 119.1(3) . . ?
O5 C21 C20 126.5(3) . . ?
O5 C21 H21 116.7 . . ?
C20 C21 H21 116.7 . . ?

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
O6 Al1 O1 C1 122.2(2) . . . . ?
O3 Al1 O1 C1 -55.9(2) . . . . ?
O5 Al1 O1 C1 -145.9(2) . . . . ?
O2 Al1 O1 C1 33.8(2) . . . . ?
O4 Al1 O1 C1 -32(3) . . . . ?
O6 Al1 O2 C7 -123.8(3) . . . . ?
O1 Al1 O2 C7 -29.3(3) . . . . ?
O3 Al1 O2 C7 59.5(3) . . . . ?
O5 Al1 O2 C7 145.9(15) . . . . ?
O4 Al1 O2 C7 148.6(2) . . . . ?
O6 Al1 O3 C8 2.8(16) . . . . ?
O1 Al1 O3 C8 153.7(3) . . . . ?
O5 Al1 O3 C8 -114.2(3) . . . . ?
O2 Al1 O3 C8 62.0(3) . . . . ?
O4 Al1 O3 C8 -25.4(3) . . . . ?
O6 Al1 O4 C14 -160.9(2) . . . . ?
O1 Al1 O4 C14 -7(3) . . . . ?
O3 Al1 O4 C14 17.2(2) . . . . ?
O5 Al1 O4 C14 107.2(2) . . . . ?
O2 Al1 O4 C14 -72.6(2) . . . . ?
O6 Al1 O5 C21 10.5(3) . . . . ?
O1 Al1 O5 C21 -84.1(3) . . . . ?
O3 Al1 O5 C21 -173.0(3) . . . . ?
O2 Al1 O5 C21 100.7(15) . . . . ?
O4 Al1 O5 C21 98.0(3) . . . . ?
O1 Al1 O6 C15 76.2(3) . . . . ?
O3 Al1 O6 C15 -133.0(15) . . . . ?
O5 Al1 O6 C15 -16.0(3) . . . . ?
O2 Al1 O6 C15 167.8(3) . . . . ?
O4 Al1 O6 C15 -104.8(3) . . . . ?
Al1 O1 C1 C2 158.8(2) . . . . ?
Al1 O1 C1 C6 -22.1(4) . . . . ?
O1 C1 C2 C3 -178.7(3) . . . . ?
C6 C1 C2 C3 2.2(5) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C2 C3 C4 C5 -2.2(5) . . . . ?
C3 C4 C5 C6 2.8(5) . . . . ?
C4 C5 C6 C7 -176.5(3) . . . . ?
C4 C5 C6 C1 -0.9(5) . . . . ?
O1 C1 C6 C7 -5.2(5) . . . . ?
C2 C1 C6 C7 173.9(3) . . . . ?
O1 C1 C6 C5 179.3(3) . . . . ?
C2 C1 C6 C5 -1.6(5) . . . . ?
Al1 O2 C7 C6 14.0(5) . . . . ?
C5 C6 C7 O2 -175.8(3) . . . . ?
C1 C6 C7 O2 8.6(5) . . . . ?
Al1 O3 C8 C9 -159.9(2) . . . . ?
Al1 O3 C8 C13 20.4(4) . . . . ?
O3 C8 C9 C10 177.2(3) . . . . ?
C13 C8 C9 C10 -3.1(5) . . . . ?
C8 C9 C10 C11 1.8(6) . . . . ?
C9 C10 C11 C12 0.7(6) . . . . ?
C10 C11 C12 C13 -1.8(6) . . . . ?
C11 C12 C13 C14 -179.4(3) . . . . ?
C11 C12 C13 C8 0.4(5) . . . . ?
O3 C8 C13 C14 1.5(5) . . . . ?
C9 C8 C13 C14 -178.2(3) . . . . ?
O3 C8 C13 C12 -178.3(3) . . . . ?
C9 C8 C13 C12 2.0(4) . . . . ?
Al1 O4 C14 C13 -4.5(4) . . . . ?
C12 C13 C14 O4 170.9(3) . . . . ?
C8 C13 C14 O4 -8.9(5) . . . . ?
Al1 O6 C15 C16 -166.5(2) . . . . ?
Al1 O6 C15 C20 14.2(4) . . . . ?
O6 C15 C16 C17 177.2(3) . . . . ?
C20 C15 C16 C17 -3.4(5) . . . . ?
C15 C16 C17 C18 3.0(5) . . . . ?
C16 C17 C18 C19 -0.4(5) . . . . ?
C17 C18 C19 C20 -1.5(5) . . . . ?
C18 C19 C20 C21 -176.3(3) . . . . ?
C18 C19 C20 C15 1.0(5) . . . . ?
O6 C15 C20 C21 -2.0(5) . . . . ?
C16 C15 C20 C21 178.7(3) . . . . ?
O6 C15 C20 C19 -179.2(3) . . . . ?
C16 C15 C20 C19 1.5(5) . . . . ?
Al1 O5 C21 C20 -3.6(5) . . . . ?
C19 C20 C21 O5 174.1(3) . . . . ?
C15 C20 C21 O5 -3.0(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 987154'
