# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2014

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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_sc1111

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 N3 O5'
_chemical_formula_weight         355.35

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           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   28.429(3)
_cell_length_b                   8.5120(7)
_cell_length_c                   15.7378(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.577(4)
_cell_angle_gamma                90.00
_cell_volume                     3375.7(5)
_cell_formula_units_Z            8
_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          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1488
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9695
_exptl_absorpt_correction_T_max  0.9846
_exptl_absorpt_process_details   sadabs

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17660
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0130
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         24.00
_reflns_number_total             2643
_reflns_number_gt                2305
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'ortep 3v2'

_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^)+(0.1982P)^2^+11.5418P] 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         2643
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0951
_refine_ls_wR_factor_ref         0.3089
_refine_ls_wR_factor_gt          0.2909
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
C5 C 0.95615(16) -0.2919(5) 1.0421(3) 0.0451(10) Uani 1 1 d . . .
C6 C 0.91858(17) -0.1864(5) 0.9831(3) 0.0445(10) Uani 1 1 d . . .
H6 H 0.8882 -0.2204 0.9296 0.053 Uiso 1 1 calc R . .
C1 C 0.92709(18) -0.0280(5) 1.0056(3) 0.0488(11) Uani 1 1 d . . .
C2 C 0.9722(2) 0.0187(6) 1.0858(3) 0.0631(13) Uani 1 1 d . . .
H2 H 0.9780 0.1250 1.1008 0.076 Uiso 1 1 calc R . .
C4 C 1.00132(18) -0.2452(6) 1.1226(4) 0.0607(13) Uani 1 1 d . . .
H4 H 1.0261 -0.3189 1.1617 0.073 Uiso 1 1 calc R . .
C3 C 1.0089(2) -0.0895(6) 1.1437(4) 0.0679(14) Uani 1 1 d . . .
H3 H 1.0390 -0.0560 1.1978 0.081 Uiso 1 1 calc R . .
C8 C 0.84077(17) 0.1152(5) 0.9661(3) 0.0542(12) Uani 1 1 d . . .
H8 H 0.8298 0.0127 0.9793 0.065 Uiso 1 1 calc R . .
C7 C 0.88791(18) 0.0921(5) 0.9444(3) 0.0527(11) Uani 1 1 d . . .
H7 H 0.9060 0.1927 0.9512 0.063 Uiso 1 1 calc R . .
C11 C 0.86045(16) 0.4822(5) 1.1152(3) 0.0435(10) Uani 1 1 d . . .
C10 C 0.84355(16) 0.3846(5) 1.0361(3) 0.0436(10) Uani 1 1 d . . .
H10 H 0.8263 0.4257 0.9745 0.052 Uiso 1 1 calc R . .
C9 C 0.85277(16) 0.2249(5) 1.0504(3) 0.0475(10) Uani 1 1 d . . .
C14 C 0.87686(19) 0.1698(6) 1.1447(3) 0.0610(13) Uani 1 1 d . . .
H14 H 0.8821 0.0623 1.1557 0.073 Uiso 1 1 calc R . .
C12 C 0.88570(18) 0.4275(6) 1.2077(3) 0.0570(12) Uani 1 1 d . . .
H12 H 0.8975 0.4962 1.2595 0.068 Uiso 1 1 calc R . .
C13 C 0.8929(2) 0.2688(7) 1.2214(3) 0.0652(14) Uani 1 1 d . . .
H13 H 0.9089 0.2281 1.2833 0.078 Uiso 1 1 calc R . .
N2 N 0.94861(15) -0.4588(4) 1.0166(3) 0.0513(10) Uani 1 1 d . . .
N1 N 0.85077(17) 0.6513(4) 1.0983(3) 0.0562(10) Uani 1 1 d . . .
O2 O 0.91313(15) -0.4961(4) 0.9379(3) 0.0672(10) Uani 1 1 d . . .
O1 O 0.97763(16) -0.5532(4) 1.0748(3) 0.0769(12) Uani 1 1 d . . .
O4 O 0.81873(19) 0.6955(4) 1.0194(3) 0.0837(13) Uani 1 1 d . . .
O3 O 0.87588(19) 0.7409(5) 1.1642(3) 0.0858(13) Uani 1 1 d . . .
O5 O 0.86388(13) 0.0447(4) 0.8467(2) 0.0594(9) Uani 1 1 d . . .
N3 N 0.79985(14) 0.1731(4) 0.8732(3) 0.0539(10) Uani 1 1 d . . .
C17 C 0.7747(2) 0.0813(7) 0.7116(4) 0.0698(14) Uani 1 1 d . . .
H17A H 0.7702 0.1381 0.6549 0.084 Uiso 1 1 calc R . .
H17B H 0.7803 -0.0291 0.7040 0.084 Uiso 1 1 calc R . .
C16 C 0.7275(2) 0.1044(7) 0.7300(4) 0.0736(15) Uani 1 1 d . . .
H16A H 0.7115 0.2066 0.7074 0.088 Uiso 1 1 calc R . .
H16B H 0.7010 0.0239 0.6979 0.088 Uiso 1 1 calc R . .
C15 C 0.7495(2) 0.0923(9) 0.8366(4) 0.0824(18) Uani 1 1 d . . .
H15A H 0.7263 0.1428 0.8579 0.099 Uiso 1 1 calc R . .
H15B H 0.7544 -0.0167 0.8570 0.099 Uiso 1 1 calc R . .
C18 C 0.81997(18) 0.1481(6) 0.8010(3) 0.0559(12) Uani 1 1 d . . .
H18 H 0.8317 0.2482 0.7863 0.067 Uiso 1 1 calc R . .

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
C5 0.049(2) 0.040(2) 0.049(2) 0.0003(18) 0.0257(19) 0.0059(18)
C6 0.054(2) 0.038(2) 0.038(2) -0.0006(16) 0.0183(18) 0.0065(17)
C1 0.063(3) 0.040(2) 0.042(2) -0.0003(18) 0.023(2) 0.0074(19)
C2 0.072(3) 0.051(3) 0.059(3) -0.015(2) 0.023(2) -0.007(2)
C4 0.049(2) 0.062(3) 0.061(3) 0.002(2) 0.017(2) 0.013(2)
C3 0.061(3) 0.066(3) 0.059(3) -0.015(2) 0.012(2) -0.002(2)
C8 0.056(3) 0.034(2) 0.048(2) 0.0029(18) 0.004(2) -0.0009(18)
C7 0.062(3) 0.040(2) 0.048(2) -0.0033(18) 0.018(2) 0.005(2)
C11 0.049(2) 0.037(2) 0.047(2) -0.0054(17) 0.0240(19) -0.0029(17)
C10 0.049(2) 0.037(2) 0.038(2) -0.0003(16) 0.0150(17) 0.0015(17)
C9 0.048(2) 0.032(2) 0.050(2) 0.0027(17) 0.0125(18) 0.0047(17)
C14 0.069(3) 0.049(3) 0.055(3) 0.012(2) 0.019(2) 0.013(2)
C12 0.058(3) 0.068(3) 0.044(2) -0.009(2) 0.022(2) -0.001(2)
C13 0.075(3) 0.073(3) 0.041(2) 0.014(2) 0.022(2) 0.016(3)
N2 0.058(2) 0.0374(19) 0.065(2) 0.0059(18) 0.034(2) 0.0101(17)
N1 0.076(3) 0.038(2) 0.062(2) -0.0103(19) 0.039(2) -0.0028(19)
O2 0.083(2) 0.0400(18) 0.075(2) -0.0093(16) 0.033(2) -0.0005(16)
O1 0.083(2) 0.047(2) 0.094(3) 0.0217(19) 0.035(2) 0.0225(18)
O4 0.115(3) 0.0395(19) 0.078(3) 0.0017(18) 0.029(2) 0.0124(19)
O3 0.120(3) 0.054(2) 0.082(3) -0.030(2) 0.045(2) -0.019(2)
O5 0.067(2) 0.0551(19) 0.0526(18) -0.0028(14) 0.0243(16) 0.0121(15)
N3 0.051(2) 0.045(2) 0.054(2) -0.0038(16) 0.0141(17) 0.0016(16)
C17 0.067(3) 0.073(3) 0.051(3) -0.004(2) 0.012(2) 0.004(3)
C16 0.066(3) 0.068(3) 0.066(3) -0.015(3) 0.013(3) -0.014(3)
C15 0.064(3) 0.103(5) 0.071(4) -0.008(3) 0.024(3) -0.033(3)
C18 0.055(2) 0.049(2) 0.052(2) 0.013(2) 0.015(2) 0.005(2)

_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
C5 C6 1.375(6) . ?
C5 C4 1.381(7) . ?
C5 N2 1.465(6) . ?
C6 C1 1.386(6) . ?
C6 H6 0.9300 . ?
C1 C2 1.378(6) . ?
C1 C7 1.490(6) . ?
C2 C3 1.373(7) . ?
C2 H2 0.9300 . ?
C4 C3 1.359(7) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C8 N3 1.469(5) . ?
C8 C9 1.525(6) . ?
C8 C7 1.542(7) . ?
C8 H8 0.9800 . ?
C7 O5 1.422(5) . ?
C7 H7 0.9800 . ?
C11 C12 1.373(6) . ?
C11 C10 1.384(6) . ?
C11 N1 1.467(6) . ?
C10 C9 1.383(6) . ?
C10 H10 0.9300 . ?
C9 C14 1.398(6) . ?
C14 C13 1.365(7) . ?
C14 H14 0.9300 . ?
C12 C13 1.368(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
N2 O1 1.210(5) . ?
N2 O2 1.223(5) . ?
N1 O4 1.210(5) . ?
N1 O3 1.218(5) . ?
O5 C18 1.421(5) . ?
N3 C15 1.446(6) . ?
N3 C18 1.505(6) . ?
C17 C16 1.510(8) . ?
C17 C18 1.511(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C16 C15 1.498(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C18 H18 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
C6 C5 C4 122.2(4) . . ?
C6 C5 N2 118.7(4) . . ?
C4 C5 N2 119.1(4) . . ?
C5 C6 C1 118.3(4) . . ?
C5 C6 H6 120.9 . . ?
C1 C6 H6 120.9 . . ?
C2 C1 C6 119.5(4) . . ?
C2 C1 C7 119.7(4) . . ?
C6 C1 C7 120.8(4) . . ?
C3 C2 C1 120.9(5) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C3 C4 C5 118.6(4) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C4 C3 C2 120.5(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
N3 C8 C9 114.5(3) . . ?
N3 C8 C7 101.0(4) . . ?
C9 C8 C7 113.8(4) . . ?
N3 C8 H8 109.1 . . ?
C9 C8 H8 109.1 . . ?
C7 C8 H8 109.1 . . ?
O5 C7 C1 110.2(3) . . ?
O5 C7 C8 104.2(3) . . ?
C1 C7 C8 114.3(4) . . ?
O5 C7 H7 109.3 . . ?
C1 C7 H7 109.3 . . ?
C8 C7 H7 109.3 . . ?
C12 C11 C10 122.9(4) . . ?
C12 C11 N1 119.2(4) . . ?
C10 C11 N1 117.9(4) . . ?
C9 C10 C11 118.9(4) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C10 C9 C14 117.7(4) . . ?
C10 C9 C8 120.8(4) . . ?
C14 C9 C8 121.4(4) . . ?
C13 C14 C9 122.1(4) . . ?
C13 C14 H14 119.0 . . ?
C9 C14 H14 119.0 . . ?
C13 C12 C11 117.9(4) . . ?
C13 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
C14 C13 C12 120.4(4) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
O1 N2 O2 123.2(4) . . ?
O1 N2 C5 118.4(4) . . ?
O2 N2 C5 118.5(4) . . ?
O4 N1 O3 123.0(4) . . ?
O4 N1 C11 118.7(4) . . ?
O3 N1 C11 118.3(4) . . ?
C18 O5 C7 103.9(3) . . ?
C15 N3 C8 114.7(4) . . ?
C15 N3 C18 106.5(4) . . ?
C8 N3 C18 107.6(3) . . ?
C16 C17 C18 102.9(4) . . ?
C16 C17 H17A 111.2 . . ?
C18 C17 H17A 111.2 . . ?
C16 C17 H17B 111.2 . . ?
C18 C17 H17B 111.2 . . ?
H17A C17 H17B 109.1 . . ?
C15 C16 C17 104.9(4) . . ?
C15 C16 H16A 110.8 . . ?
C17 C16 H16A 110.8 . . ?
C15 C16 H16B 110.8 . . ?
C17 C16 H16B 110.8 . . ?
H16A C16 H16B 108.8 . . ?
N3 C15 C16 103.7(5) . . ?
N3 C15 H15A 111.0 . . ?
C16 C15 H15A 111.0 . . ?
N3 C15 H15B 111.0 . . ?
C16 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
O5 C18 N3 104.9(3) . . ?
O5 C18 C17 114.1(4) . . ?
N3 C18 C17 107.3(4) . . ?
O5 C18 H18 110.1 . . ?
N3 C18 H18 110.1 . . ?
C17 C18 H18 110.1 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.524
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.085
_database_code_depnum_ccdc_archive 'CCDC 950404'