# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A
# This journal is © The Royal Society of Chemistry 2013

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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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,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_mo_av63a3_pbcn

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H44 N2 O6'
_chemical_formula_weight         552.69

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   15.0473(8)
_cell_length_b                   18.1959(10)
_cell_length_c                   10.7775(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2950.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9541
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      30.24

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1192
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9831
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_suppport 'magnetic support whith MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Micorfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            30505
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         30.34
_reflns_number_total             4118
_reflns_number_gt                3282
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0549P)^2^+1.3575P] 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    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4118
_refine_ls_number_parameters     216
_refine_ls_number_restraints     41
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1228
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.067
_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
N1 N 0.76798(7) 0.17890(5) 0.93197(9) 0.0172(2) Uani 1 1 d . B .
O1 O 1.03992(6) 0.10819(4) 0.41371(8) 0.0198(2) Uani 1 1 d . . .
O2 O 0.94616(6) 0.18736(4) 0.57230(8) 0.01881(19) Uani 1 1 d . . .
H2 H 0.9758 0.1609 0.5236 0.028 Uiso 1 1 calc R . .
O3 O 0.86241(6) -0.04649(4) 0.76037(9) 0.0218(2) Uani 1 1 d . . .
H3 H 0.8939 -0.0647 0.7039 0.033 Uiso 1 1 calc R . .
C1 C 1.01766(8) 0.04834(6) 0.46157(11) 0.0157(2) Uani 1 1 d . . .
C2 C 0.96146(8) 0.02810(6) 0.56566(11) 0.0147(2) Uani 1 1 d . . .
C3 C 0.91091(7) 0.06547(6) 0.65446(11) 0.0143(2) Uani 1 1 d . . .
C4 C 0.90602(7) 0.14453(6) 0.65779(11) 0.0147(2) Uani 1 1 d . . .
C5 C 0.85959(8) 0.18088(6) 0.74831(11) 0.0161(2) Uani 1 1 d . . .
H5 H 0.8580 0.2331 0.7476 0.019 Uiso 1 1 calc R . .
C6 C 0.81389(8) 0.14226(6) 0.84309(11) 0.0157(2) Uani 1 1 d . . .
C7 C 0.81731(8) 0.06442(6) 0.84122(11) 0.0169(2) Uani 1 1 d . . .
H7 H 0.7869 0.0373 0.9035 0.020 Uiso 1 1 calc R . .
C8 C 0.86372(8) 0.02754(6) 0.75123(11) 0.0157(2) Uani 1 1 d . . .
C9 C 0.76044(8) 0.25945(6) 0.93162(12) 0.0183(2) Uani 1 1 d . . .
H9A H 0.7080 0.2734 0.9818 0.022 Uiso 1 1 calc R . .
H9B H 0.7493 0.2759 0.8454 0.022 Uiso 1 1 calc R . .
C10 C 0.84185(8) 0.30104(6) 0.98177(12) 0.0196(2) Uani 1 1 d D . .
H10 H 0.8932 0.2920 0.9249 0.024 Uiso 1 1 calc R . .
C11 C 0.81970(10) 0.38322(7) 0.97953(14) 0.0271(3) Uani 1 1 d D . .
H11A H 0.7696 0.3929 1.0353 0.041 Uiso 1 1 calc R . .
H11B H 0.8038 0.3979 0.8949 0.041 Uiso 1 1 calc R . .
H11C H 0.8716 0.4114 1.0070 0.041 Uiso 1 1 calc R . .
C12 C 0.86800(9) 0.27699(7) 1.11205(12) 0.0234(3) Uani 1 1 d D . .
H12A H 0.9222 0.3028 1.1373 0.035 Uiso 1 1 calc R . .
H12B H 0.8788 0.2239 1.1128 0.035 Uiso 1 1 calc R . .
H12C H 0.8198 0.2888 1.1700 0.035 Uiso 1 1 calc R . .
C13 C 0.72079(8) 0.14118(7) 1.03259(12) 0.0200(2) Uani 1 1 d D . .
H13A H 0.7288 0.1685 1.1079 0.024 Uiso 0.90 1 d PR A 1
H13B H 0.7470 0.0936 1.0444 0.024 Uiso 0.90 1 d PR A 1
H13C H 0.7004 0.1788 1.0882 0.024 Uiso 0.10 1 d PR A 2
H13D H 0.7648 0.1135 1.0770 0.024 Uiso 0.10 1 d PR A 2
C14 C 0.62014(10) 0.13150(8) 1.00869(13) 0.0219(3) Uani 0.90 1 d PDU B 1
H14 H 0.5936 0.1813 0.9959 0.026 Uiso 0.90 1 calc PR B 1
C15 C 0.59924(10) 0.08482(8) 0.89483(14) 0.0226(3) Uani 0.90 1 d PDU B 1
H15A H 0.6220 0.0349 0.9074 0.034 Uiso 0.90 1 calc PR B 1
H15B H 0.6276 0.1065 0.8216 0.034 Uiso 0.90 1 calc PR B 1
H15C H 0.5348 0.0830 0.8823 0.034 Uiso 0.90 1 calc PR B 1
C16 C 0.57922(13) 0.09830(11) 1.12506(16) 0.0333(4) Uani 0.90 1 d PDU B 1
H16A H 0.5156 0.0902 1.1116 0.050 Uiso 0.90 1 calc PR B 1
H16B H 0.5876 0.1320 1.1950 0.050 Uiso 0.90 1 calc PR B 1
H16C H 0.6082 0.0513 1.1434 0.050 Uiso 0.90 1 calc PR B 1
C14' C 0.6431(5) 0.0905(5) 1.0102(9) 0.023(2) Uani 0.10 1 d PDU B 2
H14' H 0.6605 0.0491 0.9541 0.027 Uiso 0.10 1 calc PR B 2
C15' C 0.6098(9) 0.0612(8) 1.1346(10) 0.026(2) Uani 0.10 1 d PDU B 2
H15D H 0.6536 0.0270 1.1690 0.039 Uiso 0.10 1 calc PR B 2
H15E H 0.5531 0.0356 1.1224 0.039 Uiso 0.10 1 calc PR B 2
H15F H 0.6012 0.1023 1.1922 0.039 Uiso 0.10 1 calc PR B 2
C16' C 0.5751(9) 0.1399(7) 0.9479(12) 0.028(2) Uani 0.10 1 d PDU B 2
H16D H 0.5507 0.1743 1.0090 0.042 Uiso 0.10 1 calc PR B 2
H16E H 0.5270 0.1098 0.9135 0.042 Uiso 0.10 1 calc PR B 2
H16F H 0.6038 0.1675 0.8809 0.042 Uiso 0.10 1 calc PR B 2

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
N1 0.0190(5) 0.0136(4) 0.0189(5) -0.0025(4) 0.0035(4) 0.0005(4)
O1 0.0248(4) 0.0117(4) 0.0228(5) 0.0001(3) 0.0070(4) -0.0002(3)
O2 0.0243(4) 0.0125(4) 0.0196(4) 0.0010(3) 0.0066(4) 0.0024(3)
O3 0.0301(5) 0.0112(4) 0.0242(5) -0.0009(3) 0.0104(4) 0.0003(3)
C1 0.0160(5) 0.0131(5) 0.0181(6) -0.0013(4) 0.0004(4) 0.0004(4)
C2 0.0149(5) 0.0118(5) 0.0176(5) -0.0009(4) -0.0007(4) 0.0000(4)
C3 0.0143(5) 0.0123(5) 0.0163(5) -0.0007(4) -0.0007(4) 0.0011(4)
C4 0.0143(5) 0.0136(5) 0.0163(5) 0.0009(4) -0.0012(4) 0.0006(4)
C5 0.0182(5) 0.0121(5) 0.0180(5) -0.0014(4) -0.0006(4) 0.0020(4)
C6 0.0155(5) 0.0149(5) 0.0167(5) -0.0020(4) -0.0010(4) 0.0013(4)
C7 0.0189(6) 0.0135(5) 0.0184(6) -0.0005(4) 0.0024(5) 0.0002(4)
C8 0.0164(5) 0.0128(5) 0.0179(5) -0.0007(4) -0.0010(4) 0.0005(4)
C9 0.0198(6) 0.0138(5) 0.0214(6) -0.0036(4) 0.0032(5) 0.0023(4)
C10 0.0202(6) 0.0156(5) 0.0231(6) -0.0041(4) 0.0045(5) 0.0000(4)
C11 0.0317(7) 0.0162(6) 0.0335(7) -0.0016(5) 0.0032(6) -0.0011(5)
C12 0.0249(6) 0.0188(6) 0.0265(7) -0.0052(5) -0.0013(5) 0.0003(5)
C13 0.0238(6) 0.0182(5) 0.0180(6) -0.0030(4) 0.0049(5) -0.0011(4)
C14 0.0201(7) 0.0187(7) 0.0268(7) -0.0023(5) 0.0043(6) -0.0002(5)
C15 0.0213(7) 0.0202(6) 0.0263(7) 0.0007(5) -0.0008(6) -0.0010(5)
C16 0.0307(9) 0.0406(10) 0.0287(8) -0.0062(7) 0.0106(7) -0.0112(8)
C14' 0.022(5) 0.020(5) 0.027(5) -0.001(4) 0.006(4) 0.001(4)
C15' 0.022(6) 0.030(6) 0.026(6) 0.000(4) 0.009(5) -0.001(5)
C16' 0.024(6) 0.028(6) 0.031(6) -0.001(4) -0.003(5) -0.001(4)

_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
N1 C6 1.3562(15) . ?
N1 C13 1.4667(15) . ?
N1 C9 1.4700(14) . ?
O1 C1 1.2507(14) . ?
O2 C4 1.3495(14) . ?
O3 C8 1.3508(13) . ?
C1 C2 1.4523(16) . ?
C1 C2 1.4558(15) 5_756 ?
C1 C1 2.016(2) 5_756 ?
C2 C3 1.3988(16) . ?
C2 C1 1.4559(15) 5_756 ?
C3 C8 1.4382(16) . ?
C3 C4 1.4409(15) . ?
C4 C5 1.3702(16) . ?
C5 C6 1.4178(16) . ?
C6 C7 1.4175(15) . ?
C7 C8 1.3706(16) . ?
C9 C10 1.5379(17) . ?
C10 C12 1.5224(17) . ?
C10 C11 1.5324(16) . ?
C13 C14' 1.509(5) . ?
C13 C14 1.5464(18) . ?
C14 C16 1.522(2) . ?
C14 C15 1.5252(19) . ?
C14' C16' 1.519(5) . ?
C14' C15' 1.527(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
C6 N1 C13 122.60(10) . . ?
C6 N1 C9 121.84(10) . . ?
C13 N1 C9 115.53(9) . . ?
O1 C1 C2 134.05(11) . . ?
O1 C1 C2 133.70(11) . 5_756 ?
C2 C1 C2 92.25(9) . 5_756 ?
O1 C1 C1 179.72(14) . 5_756 ?
C2 C1 C1 46.20(6) . 5_756 ?
C2 C1 C1 46.05(6) 5_756 5_756 ?
C3 C2 C1 136.21(10) . . ?
C3 C2 C1 136.02(11) . 5_756 ?
C1 C2 C1 87.76(9) . 5_756 ?
C2 C3 C8 122.10(10) . . ?
C2 C3 C4 122.01(10) . . ?
C8 C3 C4 115.83(10) . . ?
O2 C4 C5 115.82(10) . . ?
O2 C4 C3 122.45(10) . . ?
C5 C4 C3 121.72(10) . . ?
C4 C5 C6 121.40(10) . . ?
N1 C6 C7 121.31(11) . . ?
N1 C6 C5 120.82(10) . . ?
C7 C6 C5 117.87(10) . . ?
C8 C7 C6 121.18(11) . . ?
O3 C8 C7 115.42(10) . . ?
O3 C8 C3 122.59(10) . . ?
C7 C8 C3 121.99(10) . . ?
N1 C9 C10 115.35(10) . . ?
C12 C10 C11 110.56(10) . . ?
C12 C10 C9 112.86(10) . . ?
C11 C10 C9 107.54(10) . . ?
N1 C13 C14' 122.9(4) . . ?
N1 C13 C14 113.85(11) . . ?
C14' C13 C14 31.2(4) . . ?
C16 C14 C15 111.00(12) . . ?
C16 C14 C13 107.70(13) . . ?
C15 C14 C13 113.54(11) . . ?
C13 C14' C16' 103.3(8) . . ?
C13 C14' C15' 109.1(8) . . ?
C16' C14' C15' 111.9(6) . . ?

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
O1 C1 C2 C3 -0.9(2) . . . . ?
C2 C1 C2 C3 178.92(17) 5_756 . . . ?
C1 C1 C2 C3 178.92(17) 5_756 . . . ?
O1 C1 C2 C1 -179.82(18) . . . 5_756 ?
C2 C1 C2 C1 0.0 5_756 . . 5_756 ?
C1 C2 C3 C8 -177.67(12) . . . . ?
C1 C2 C3 C8 0.8(2) 5_756 . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C1 C2 C3 C4 178.06(12) 5_756 . . . ?
C2 C3 C4 O2 3.28(17) . . . . ?
C8 C3 C4 O2 -179.28(10) . . . . ?
C2 C3 C4 C5 -177.05(11) . . . . ?
C8 C3 C4 C5 0.39(16) . . . . ?
O2 C4 C5 C6 179.55(10) . . . . ?
C3 C4 C5 C6 -0.14(17) . . . . ?
C13 N1 C6 C7 1.30(18) . . . . ?
C9 N1 C6 C7 -177.09(11) . . . . ?
C13 N1 C6 C5 -179.16(11) . . . . ?
C9 N1 C6 C5 2.46(17) . . . . ?
C4 C5 C6 N1 -179.82(11) . . . . ?
C4 C5 C6 C7 -0.26(17) . . . . ?
N1 C6 C7 C8 179.96(11) . . . . ?
C5 C6 C7 C8 0.40(17) . . . . ?
C6 C7 C8 O3 179.46(11) . . . . ?
C6 C7 C8 C3 -0.15(18) . . . . ?
C2 C3 C8 O3 -2.39(18) . . . . ?
C4 C3 C8 O3 -179.82(11) . . . . ?
C2 C3 C8 C7 177.19(11) . . . . ?
C4 C3 C8 C7 -0.25(17) . . . . ?
C6 N1 C9 C10 -79.37(14) . . . . ?
C13 N1 C9 C10 102.14(12) . . . . ?
N1 C9 C10 C12 -55.20(14) . . . . ?
N1 C9 C10 C11 -177.41(10) . . . . ?
C6 N1 C13 C14' -63.9(5) . . . . ?
C9 N1 C13 C14' 114.6(5) . . . . ?
C6 N1 C13 C14 -98.02(14) . . . . ?
C9 N1 C13 C14 80.46(13) . . . . ?
N1 C13 C14 C16 -174.84(12) . . . . ?
C14' C13 C14 C16 70.6(7) . . . . ?
N1 C13 C14 C15 61.83(15) . . . . ?
C14' C13 C14 C15 -52.7(7) . . . . ?
N1 C13 C14' C16' -60.5(8) . . . . ?
C14 C13 C14' C16' 21.6(6) . . . . ?
N1 C13 C14' C15' -179.7(6) . . . . ?
C14 C13 C14' C15' -97.6(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.927
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 940816'