# Supplementary Material (ESI) for Chemical Science
# This journal is (c) The Royal Society of Chemistry 2011

data_global

_journal_coden_Cambridge         1475

loop_
_publ_author_name
'Elisabetta Iengo'

_publ_contact_author_name        'Elisabetta Iengo'
_publ_contact_author_address     
;

;

_publ_contact_author_email       eiengo@units.it

data_js0617
_database_code_depnum_ccdc_archive 'CCDC 804310'
#TrackingRef 'js0617.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H30 N2 O4'
_chemical_formula_sum            'C26 H30 N2 O4'
_chemical_formula_weight         434.52

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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.8231(2)
_cell_length_b                   8.3044(3)
_cell_length_c                   14.2640(6)
_cell_angle_alpha                96.566(2)
_cell_angle_beta                 97.473(2)
_cell_angle_gamma                92.996(2)
_cell_volume                     561.44(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    8275
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      32.58

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             232
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.863
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;

_exptl_special_details           
;
The hexyl group is poorly resolved: this moiety was modelled (with
bond length constraints and common, isotropic displacement parameters)
as disordered over two sites, occupancies 0.55, 0.45 (JED).
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice \w and \f scans'
_diffrn_reflns_number            10430
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.58
_diffrn_reflns_theta_max         32.53
_reflns_number_total             4026
_reflns_number_gt                2362
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_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^)+(0.1421P)^2^+0.3897P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4026
_refine_ls_number_parameters     141
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1532
_refine_ls_R_factor_gt           0.0966
_refine_ls_wR_factor_ref         0.3050
_refine_ls_wR_factor_gt          0.2574
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.047
_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
N1 N 0.7922(4) 0.2883(2) 0.34598(13) 0.0333(4) Uani 1 1 d . B .
O1 O 0.4119(4) 0.1209(2) 0.27995(13) 0.0457(5) Uani 1 1 d . . .
O2 O 1.1744(4) 0.4546(2) 0.41097(13) 0.0438(5) Uani 1 1 d . . .
C1 C 0.6258(4) 0.1437(3) 0.33685(15) 0.0332(4) Uani 1 1 d . . .
C2 C 0.7194(4) 0.0206(2) 0.39999(14) 0.0296(4) Uani 1 1 d . . .
C3 C 0.5679(4) -0.1268(3) 0.39311(15) 0.0327(4) Uani 1 1 d . . .
H3 H 0.4080 -0.1513 0.3462 0.049 Uiso 1 1 calc R . .
C4 C 1.0364(4) 0.3268(3) 0.41001(15) 0.0324(4) Uani 1 1 d . . .
C5 C 1.1178(4) 0.2073(2) 0.47654(14) 0.0287(4) Uani 1 1 d . . .
C6 C 1.3511(4) 0.2413(3) 0.54469(15) 0.0327(4) Uani 1 1 d . . .
H6 H 1.4573 0.3423 0.5496 0.049 Uiso 1 1 calc R . .
C7 C 0.9586(4) 0.0574(2) 0.46891(14) 0.0273(4) Uani 1 1 d . . .
C1' C 0.7080(5) 0.4089(3) 0.28070(17) 0.0402(5) Uani 1 1 d D . .
H1'A H 0.7787 0.5189 0.3114 0.060 Uiso 1 1 calc R A 1
H1'B H 0.5009 0.4066 0.2689 0.060 Uiso 1 1 calc R A 1
C2' C 0.8197(6) 0.3762(3) 0.18645(18) 0.0474(6) Uani 0.499(5) 1 d PD B 1
H2'A H 1.0269 0.3815 0.1993 0.057 Uiso 0.499(5) 1 calc PR B 1
H2'B H 0.7560 0.2637 0.1584 0.057 Uiso 0.499(5) 1 calc PR B 1
C3' C 0.7388(14) 0.4862(7) 0.1143(4) 0.0465(9) Uiso 0.499(5) 1 d PD B 1
H3'A H 0.5318 0.4812 0.1002 0.056 Uiso 0.499(5) 1 calc PR B 1
H3'B H 0.8126 0.4479 0.0547 0.056 Uiso 0.499(5) 1 calc PR B 1
C4' C 0.8467(16) 0.6601(8) 0.1463(5) 0.0581(11) Uiso 0.499(5) 1 d PD B 1
H4'A H 1.0522 0.6646 0.1651 0.070 Uiso 0.499(5) 1 calc PR B 1
H4'B H 0.7609 0.7018 0.2029 0.070 Uiso 0.499(5) 1 calc PR B 1
C5' C 0.778(2) 0.7713(11) 0.0655(7) 0.0895(18) Uiso 0.499(5) 1 d PD B 1
H5'A H 0.8878 0.7421 0.0128 0.107 Uiso 0.499(5) 1 calc PR B 1
H5'B H 0.5763 0.7559 0.0398 0.107 Uiso 0.499(5) 1 calc PR B 1
C6' C 0.851(3) 0.9452(13) 0.1070(9) 0.123(3) Uiso 0.499(5) 1 d PD B 1
H6'A H 0.8237 1.0155 0.0564 0.184 Uiso 0.499(5) 1 calc PR B 1
H6'B H 1.0477 0.9576 0.1364 0.184 Uiso 0.499(5) 1 calc PR B 1
H6'C H 0.7303 0.9758 0.1554 0.184 Uiso 0.499(5) 1 calc PR B 1
C2" C 0.8197(6) 0.3762(3) 0.18645(18) 0.0474(6) Uani 0.501(5) 1 d PD B 2
H2"A H 0.7179 0.2791 0.1480 0.057 Uiso 0.501(5) 1 calc PR B 2
H2"B H 1.0215 0.3568 0.1972 0.057 Uiso 0.501(5) 1 calc PR B 2
C3" C 0.7736(13) 0.5322(7) 0.1329(4) 0.0465(9) Uiso 0.501(5) 1 d PD B 2
H3"A H 0.8098 0.5052 0.0664 0.056 Uiso 0.501(5) 1 calc PR B 2
H3"B H 0.5742 0.5565 0.1307 0.056 Uiso 0.501(5) 1 calc PR B 2
C4" C 0.9510(16) 0.6828(7) 0.1755(5) 0.0581(11) Uiso 0.501(5) 1 d PD B 2
H4"A H 1.1469 0.6542 0.1912 0.070 Uiso 0.501(5) 1 calc PR B 2
H4"B H 0.8845 0.7258 0.2357 0.070 Uiso 0.501(5) 1 calc PR B 2
C5" C 0.946(2) 0.8146(11) 0.1104(7) 0.0895(18) Uiso 0.501(5) 1 d PD B 2
H5"A H 1.0636 0.9103 0.1441 0.107 Uiso 0.501(5) 1 calc PR B 2
H5"B H 1.0328 0.7751 0.0537 0.107 Uiso 0.501(5) 1 calc PR B 2
C6" C 0.669(3) 0.8669(17) 0.0782(9) 0.123(3) Uiso 0.501(5) 1 d PD B 2
H6"A H 0.6895 0.9661 0.0478 0.184 Uiso 0.501(5) 1 calc PR B 2
H6"B H 0.5671 0.8886 0.1329 0.184 Uiso 0.501(5) 1 calc PR B 2
H6"C H 0.5648 0.7812 0.0322 0.184 Uiso 0.501(5) 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 0.0303(9) 0.0345(9) 0.0369(9) 0.0120(7) 0.0042(7) 0.0032(7)
O1 0.0363(9) 0.0524(10) 0.0466(10) 0.0162(8) -0.0080(7) -0.0020(7)
O2 0.0446(10) 0.0345(8) 0.0536(10) 0.0142(7) 0.0070(7) -0.0064(7)
C1 0.0287(10) 0.0379(11) 0.0336(10) 0.0084(8) 0.0040(7) 0.0013(8)
C2 0.0254(9) 0.0323(10) 0.0313(9) 0.0059(7) 0.0040(7) -0.0002(7)
C3 0.0277(9) 0.0355(10) 0.0326(10) 0.0021(8) -0.0003(7) -0.0040(8)
C4 0.0305(10) 0.0314(10) 0.0367(10) 0.0064(8) 0.0089(8) 0.0005(7)
C5 0.0258(9) 0.0273(9) 0.0334(10) 0.0038(7) 0.0065(7) -0.0024(7)
C6 0.0304(10) 0.0287(9) 0.0378(11) 0.0024(8) 0.0044(8) -0.0062(7)
C7 0.0230(8) 0.0289(9) 0.0303(9) 0.0035(7) 0.0057(7) -0.0008(7)
C1' 0.0366(11) 0.0422(12) 0.0458(12) 0.0185(10) 0.0068(9) 0.0077(9)
C2' 0.0522(15) 0.0515(14) 0.0417(13) 0.0171(11) 0.0063(10) 0.0080(11)
C2" 0.0522(15) 0.0515(14) 0.0417(13) 0.0171(11) 0.0063(10) 0.0080(11)

_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 C4 1.392(3) . ?
N1 C1 1.393(3) . ?
N1 C1' 1.481(3) . ?
O1 C1 1.219(3) . ?
O2 C4 1.221(3) . ?
C1 C2 1.487(3) . ?
C2 C3 1.379(3) . ?
C2 C7 1.411(3) . ?
C3 C6 1.409(3) 2_756 ?
C3 H3 0.9500 . ?
C4 C5 1.483(3) . ?
C5 C6 1.382(3) . ?
C5 C7 1.414(3) . ?
C6 C3 1.409(3) 2_756 ?
C6 H6 0.9500 . ?
C7 C7 1.413(4) 2_756 ?
C1' C2' 1.514(3) . ?
C1' H1'A 0.9900 . ?
C1' H1'B 0.9900 . ?
C2' C3' 1.481(6) . ?
C2' H2'A 0.9900 . ?
C2' H2'B 0.9900 . ?
C3' C4' 1.508(8) . ?
C3' H3'A 0.9900 . ?
C3' H3'B 0.9900 . ?
C4' C5' 1.571(10) . ?
C4' H4'A 0.9900 . ?
C4' H4'B 0.9900 . ?
C5' C6' 1.503(12) . ?
C5' H5'A 0.9900 . ?
C5' H5'B 0.9900 . ?
C6' H6'A 0.9800 . ?
C6' H6'B 0.9800 . ?
C6' H6'C 0.9800 . ?
C3" C4" 1.499(8) . ?
C3" H3"A 0.9900 . ?
C3" H3"B 0.9900 . ?
C4" C5" 1.513(10) . ?
C4" H4"A 0.9900 . ?
C4" H4"B 0.9900 . ?
C5" C6" 1.459(12) . ?
C5" H5"A 0.9900 . ?
C5" H5"B 0.9900 . ?
C6" H6"A 0.9800 . ?
C6" H6"B 0.9800 . ?
C6" H6"C 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
C4 N1 C1 125.11(18) . . ?
C4 N1 C1' 117.24(18) . . ?
C1 N1 C1' 117.62(18) . . ?
O1 C1 N1 120.9(2) . . ?
O1 C1 C2 122.0(2) . . ?
N1 C1 C2 117.09(18) . . ?
C3 C2 C7 120.18(19) . . ?
C3 C2 C1 120.11(18) . . ?
C7 C2 C1 119.68(18) . . ?
C2 C3 C6 120.40(19) . 2_756 ?
C2 C3 H3 119.8 . . ?
C6 C3 H3 119.8 2_756 . ?
O2 C4 N1 120.7(2) . . ?
O2 C4 C5 122.1(2) . . ?
N1 C4 C5 117.21(18) . . ?
C6 C5 C7 120.17(19) . . ?
C6 C5 C4 120.10(18) . . ?
C7 C5 C4 119.72(18) . . ?
C5 C6 C3 120.25(19) . 2_756 ?
C5 C6 H6 119.9 . . ?
C3 C6 H6 119.9 2_756 . ?
C2 C7 C7 119.6(2) . 2_756 ?
C2 C7 C5 121.01(18) . . ?
C7 C7 C5 119.4(2) 2_756 . ?
N1 C1' C2' 112.2(2) . . ?
N1 C1' H1'A 109.2 . . ?
C2' C1' H1'A 109.2 . . ?
N1 C1' H1'B 109.2 . . ?
C2' C1' H1'B 109.2 . . ?
H1'A C1' H1'B 107.9 . . ?
C3' C2' C1' 116.6(3) . . ?
C3' C2' H2'A 108.1 . . ?
C1' C2' H2'A 108.1 . . ?
C3' C2' H2'B 108.1 . . ?
C1' C2' H2'B 108.1 . . ?
H2'A C2' H2'B 107.3 . . ?
C2' C3' C4' 112.8(5) . . ?
C2' C3' H3'A 109.0 . . ?
C4' C3' H3'A 109.0 . . ?
C2' C3' H3'B 109.0 . . ?
C4' C3' H3'B 109.0 . . ?
H3'A C3' H3'B 107.8 . . ?
C3' C4' C5' 111.7(6) . . ?
C3' C4' H4'A 109.3 . . ?
C5' C4' H4'A 109.3 . . ?
C3' C4' H4'B 109.3 . . ?
C5' C4' H4'B 109.3 . . ?
H4'A C4' H4'B 107.9 . . ?
C6' C5' C4' 108.5(8) . . ?
C6' C5' H5'A 110.0 . . ?
C4' C5' H5'A 110.0 . . ?
C6' C5' H5'B 110.0 . . ?
C4' C5' H5'B 110.0 . . ?
H5'A C5' H5'B 108.4 . . ?
C4" C3" H3"A 108.3 . . ?
C4" C3" H3"B 108.3 . . ?
H3"A C3" H3"B 107.4 . . ?
C3" C4" C5" 113.3(6) . . ?
C3" C4" H4"A 108.9 . . ?
C5" C4" H4"A 108.9 . . ?
C3" C4" H4"B 108.9 . . ?
C5" C4" H4"B 108.9 . . ?
H4"A C4" H4"B 107.7 . . ?
C6" C5" C4" 115.6(8) . . ?
C6" C5" H5"A 108.4 . . ?
C4" C5" H5"A 108.4 . . ?
C6" C5" H5"B 108.4 . . ?
C4" C5" H5"B 108.4 . . ?
H5"A C5" H5"B 107.4 . . ?
C5" C6" H6"A 109.5 . . ?
C5" C6" H6"B 109.5 . . ?
H6"A C6" H6"B 109.5 . . ?
C5" C6" H6"C 109.5 . . ?
H6"A C6" H6"C 109.5 . . ?
H6"B C6" H6"C 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
C4 N1 C1 O1 178.7(2) . . . . ?
C1' N1 C1 O1 -3.2(3) . . . . ?
C4 N1 C1 C2 -0.7(3) . . . . ?
C1' N1 C1 C2 177.43(18) . . . . ?
O1 C1 C2 C3 2.1(3) . . . . ?
N1 C1 C2 C3 -178.47(19) . . . . ?
O1 C1 C2 C7 -175.9(2) . . . . ?
N1 C1 C2 C7 3.5(3) . . . . ?
C7 C2 C3 C6 0.6(3) . . . 2_756 ?
C1 C2 C3 C6 -177.41(19) . . . 2_756 ?
C1 N1 C4 O2 177.6(2) . . . . ?
C1' N1 C4 O2 -0.5(3) . . . . ?
C1 N1 C4 C5 -2.9(3) . . . . ?
C1' N1 C4 C5 178.91(18) . . . . ?
O2 C4 C5 C6 2.3(3) . . . . ?
N1 C4 C5 C6 -177.14(19) . . . . ?
O2 C4 C5 C7 -176.6(2) . . . . ?
N1 C4 C5 C7 3.9(3) . . . . ?
C7 C5 C6 C3 0.1(3) . . . 2_756 ?
C4 C5 C6 C3 -178.82(19) . . . 2_756 ?
C3 C2 C7 C7 -0.3(3) . . . 2_756 ?
C1 C2 C7 C7 177.7(2) . . . 2_756 ?
C3 C2 C7 C5 179.49(19) . . . . ?
C1 C2 C7 C5 -2.5(3) . . . . ?
C6 C5 C7 C2 179.82(19) . . . . ?
C4 C5 C7 C2 -1.3(3) . . . . ?
C6 C5 C7 C7 -0.4(3) . . . 2_756 ?
C4 C5 C7 C7 178.5(2) . . . 2_756 ?
C4 N1 C1' C2' 92.9(3) . . . . ?
C1 N1 C1' C2' -85.3(3) . . . . ?
N1 C1' C2' C3' 177.8(3) . . . . ?
C1' C2' C3' C4' 62.8(6) . . . . ?
C2' C3' C4' C5' 175.6(6) . . . . ?
C3' C4' C5' C6' 171.4(9) . . . . ?
C3" C4" C5" C6" 56.8(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        32.53
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.784
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.101