# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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#                                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
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H21 N3 O5'
_chemical_formula_sum            'C17 H21 N3 O5'
_chemical_formula_weight         347.37

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   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   9.491(4)
_cell_length_b                   9.123(4)
_cell_length_c                   10.884(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.727(19)
_cell_angle_gamma                90.00
_cell_volume                     902.5(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2125
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      24.57

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6216
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   
'SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction'

_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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4731
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2912
_reflns_number_gt                2278
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Sir-92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
There is disorder in the oxygen atoms of nitro group and resolved with fixing
their bond distances with N...O = 1.210 Å.
 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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

_chemical_absolute_configuration unk
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(3)
_refine_ls_number_reflns         2912
_refine_ls_number_parameters     239
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0817
_refine_ls_wR_factor_ref         0.3395
_refine_ls_wR_factor_gt          0.2611
_refine_ls_goodness_of_fit_ref   1.413
_refine_ls_restrained_S_all      1.432
_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
C1 C 0.6973(12) -0.4179(10) 0.6832(9) 0.086(3) Uani 1 1 d . . .
H1A H 0.7803 -0.4681 0.7308 0.103 Uiso 1 1 calc R . .
H1B H 0.6550 -0.4410 0.5972 0.103 Uiso 1 1 calc R . .
C2 C 0.6402(8) -0.3150(9) 0.7369(8) 0.073(2) Uani 1 1 d . . .
H2 H 0.5571 -0.2657 0.6881 0.087 Uiso 1 1 calc R . .
C3 C 0.7053(10) -0.2733(7) 0.8770(7) 0.0623(19) Uani 1 1 d . . .
H3A H 0.6425 -0.3097 0.9265 0.075 Uiso 1 1 calc R . .
H3B H 0.8013 -0.3185 0.9101 0.075 Uiso 1 1 calc R . .
C4 C 0.6268(8) -0.0251(7) 0.9320(5) 0.0480(15) Uani 1 1 d . . .
C5 C 0.8311(7) -0.0274(6) 0.8649(6) 0.0435(14) Uani 1 1 d . . .
C6 C 0.9517(9) -0.0774(7) 0.8252(7) 0.0590(18) Uani 1 1 d . . .
H6 H 0.9657 -0.1764 0.8123 0.071 Uiso 1 1 calc R . .
C7 C 1.0489(8) 0.0287(8) 0.8062(6) 0.0558(17) Uani 1 1 d . . .
H7 H 1.1274 -0.0010 0.7770 0.067 Uiso 1 1 calc R . .
C8 C 1.0340(7) 0.1744(8) 0.8286(6) 0.0555(17) Uani 1 1 d . . .
H8 H 1.1027 0.2419 0.8173 0.067 Uiso 1 1 calc R . .
C9 C 0.9124(7) 0.2213(6) 0.8694(5) 0.0468(14) Uani 1 1 d . . .
H9 H 0.8994 0.3203 0.8834 0.056 Uiso 1 1 calc R . .
C10 C 0.8128(6) 0.1188(6) 0.8883(5) 0.0412(13) Uani 1 1 d . . .
C11 C 0.6732(7) 0.1382(6) 0.9295(5) 0.0436(14) Uani 1 1 d . . .
C12 C 0.5559(8) 0.2253(7) 0.8383(6) 0.0573(17) Uani 1 1 d . A .
H12A H 0.4716 0.2307 0.8717 0.069 Uiso 1 1 calc R . .
H12B H 0.5918 0.3244 0.8354 0.069 Uiso 1 1 calc R . .
C13 C 0.7709(6) 0.1373(6) 1.1632(5) 0.0426(13) Uani 1 1 d . . .
C14 C 0.7561(12) 0.0148(10) 1.4153(9) 0.084(3) Uani 1 1 d . . .
H14A H 0.6546 0.0321 1.4093 0.126 Uiso 1 1 calc R . .
H14B H 0.8050 -0.0264 1.4977 0.126 Uiso 1 1 calc R . .
H14C H 0.7627 -0.0521 1.3491 0.126 Uiso 1 1 calc R . .
C15 C 0.8301(7) 0.1606(8) 1.3989(5) 0.0520(16) Uani 1 1 d . . .
C16 C 0.7810(11) 0.2774(12) 1.4758(7) 0.087(3) Uani 1 1 d . . .
H16A H 0.7893 0.3719 1.4397 0.130 Uiso 1 1 calc R . .
H16B H 0.8420 0.2743 1.5630 0.130 Uiso 1 1 calc R . .
H16C H 0.6805 0.2602 1.4734 0.130 Uiso 1 1 calc R . .
C17 C 0.9883(9) 0.1503(13) 1.4282(8) 0.083(3) Uani 1 1 d . . .
H17A H 1.0133 0.0717 1.3797 0.124 Uiso 1 1 calc R . .
H17B H 1.0299 0.1316 1.5182 0.124 Uiso 1 1 calc R . .
H17C H 1.0266 0.2408 1.4061 0.124 Uiso 1 1 calc R . .
N1 N 0.7199(7) -0.1113(5) 0.8915(5) 0.0497(14) Uani 1 1 d . . .
N2 N 0.5055(8) 0.1674(8) 0.7048(5) 0.078(2) Uani 1 1 d D . .
N3 N 0.6966(6) 0.2065(5) 1.0547(4) 0.0474(12) Uani 1 1 d . . .
H3 H 0.6622 0.2928 1.0594 0.057 Uiso 1 1 calc R . .
O1 O 0.5183(7) -0.0634(5) 0.9660(5) 0.0714(16) Uani 1 1 d . . .
O2 O 0.8416(6) 0.0257(5) 1.1645(5) 0.0656(14) Uani 1 1 d . . .
O3 O 0.7596(5) 0.2130(4) 1.2651(4) 0.0495(11) Uani 1 1 d . . .
O4 O 0.503(2) 0.0458(11) 0.6744(10) 0.143(7) Uani 0.660(12) 1 d PD A 1
O4' O 0.386(3) 0.107(2) 0.684(2) 0.143(7) Uani 0.340(12) 1 d PD A 2
O5 O 0.594(4) 0.207(4) 0.644(3) 0.134(6) Uani 0.35(2) 1 d PD A 1
O5' O 0.505(2) 0.260(2) 0.6175(12) 0.134(6) Uani 0.65(2) 1 d PD A 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
C1 C2 1.304(11) . ?
C1 H1A 0.9300 . ?
C1 H1B 0.9300 . ?
C2 C3 1.520(11) . ?
C2 H2 0.9300 . ?
C3 N1 1.489(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O1 1.241(8) . ?
C4 N1 1.348(9) . ?
C4 C11 1.556(8) . ?
C5 C10 1.378(8) . ?
C5 N1 1.400(8) . ?
C5 C6 1.411(10) . ?
C6 C7 1.393(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.367(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.416(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.386(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.527(9) . ?
C11 N3 1.456(7) . ?
C11 C12 1.490(9) . ?
C12 N2 1.490(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O2 1.217(8) . ?
C13 O3 1.336(7) . ?
C13 N3 1.346(7) . ?
C14 C15 1.538(12) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C17 1.445(10) . ?
C15 O3 1.495(7) . ?
C15 C16 1.509(11) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N2 O4 1.157(11) . ?
N2 O4' 1.220(18) . ?
N2 O5 1.256(18) . ?
N2 O5' 1.272(14) . ?
N3 H3 0.8600 . ?
O4 O5 1.78(3) . ?

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
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C1 C2 C3 121.9(8) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
N1 C3 C2 110.7(6) . . ?
N1 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
O1 C4 N1 127.7(6) . . ?
O1 C4 C11 122.6(6) . . ?
N1 C4 C11 109.7(5) . . ?
C10 C5 N1 110.4(6) . . ?
C10 C5 C6 121.7(6) . . ?
N1 C5 C6 127.9(5) . . ?
C7 C6 C5 116.8(6) . . ?
C7 C6 H6 121.6 . . ?
C5 C6 H6 121.6 . . ?
C8 C7 C6 122.8(7) . . ?
C8 C7 H7 118.6 . . ?
C6 C7 H7 118.6 . . ?
C7 C8 C9 119.1(7) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 119.6(5) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C5 C10 C9 119.9(6) . . ?
C5 C10 C11 109.4(5) . . ?
C9 C10 C11 130.7(5) . . ?
N3 C11 C12 106.2(5) . . ?
N3 C11 C10 114.4(5) . . ?
C12 C11 C10 114.3(5) . . ?
N3 C11 C4 111.1(4) . . ?
C12 C11 C4 111.1(5) . . ?
C10 C11 C4 99.7(5) . . ?
N2 C12 C11 115.4(6) . . ?
N2 C12 H12A 108.4 . . ?
C11 C12 H12A 108.4 . . ?
N2 C12 H12B 108.4 . . ?
C11 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
O2 C13 O3 126.8(5) . . ?
O2 C13 N3 123.4(5) . . ?
O3 C13 N3 109.8(5) . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C15 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C17 C15 O3 112.4(5) . . ?
C17 C15 C16 113.0(7) . . ?
O3 C15 C16 101.0(5) . . ?
C17 C15 C14 113.5(7) . . ?
O3 C15 C14 107.3(6) . . ?
C16 C15 C14 108.8(7) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 N1 C5 110.7(5) . . ?
C4 N1 C3 124.4(6) . . ?
C5 N1 C3 125.0(6) . . ?
O4 N2 O4' 64.9(14) . . ?
O4 N2 O5 94.8(19) . . ?
O4' N2 O5 139.1(18) . . ?
O4 N2 O5' 115.4(11) . . ?
O4' N2 O5' 111.1(15) . . ?
O4 N2 C12 126.4(8) . . ?
O4' N2 C12 111.1(11) . . ?
O5 N2 C12 109.5(15) . . ?
O5' N2 C12 115.1(9) . . ?
C13 N3 C11 121.4(5) . . ?
C13 N3 H3 119.3 . . ?
C11 N3 H3 119.3 . . ?
C13 O3 C15 121.5(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
C1 C2 C3 N1 132.6(9) . . . . ?
C10 C5 C6 C7 -2.2(10) . . . . ?
N1 C5 C6 C7 -179.3(6) . . . . ?
C5 C6 C7 C8 2.3(10) . . . . ?
C6 C7 C8 C9 -1.9(10) . . . . ?
C7 C8 C9 C10 1.3(8) . . . . ?
N1 C5 C10 C9 179.3(5) . . . . ?
C6 C5 C10 C9 1.8(9) . . . . ?
N1 C5 C10 C11 -2.4(7) . . . . ?
C6 C5 C10 C11 -180.0(6) . . . . ?
C8 C9 C10 C5 -1.3(8) . . . . ?
C8 C9 C10 C11 -179.1(5) . . . . ?
C5 C10 C11 N3 122.1(5) . . . . ?
C9 C10 C11 N3 -59.9(7) . . . . ?
C5 C10 C11 C12 -115.2(6) . . . . ?
C9 C10 C11 C12 62.8(8) . . . . ?
C5 C10 C11 C4 3.4(6) . . . . ?
C9 C10 C11 C4 -178.6(6) . . . . ?
O1 C4 C11 N3 56.2(8) . . . . ?
N1 C4 C11 N3 -124.4(5) . . . . ?
O1 C4 C11 C12 -61.8(8) . . . . ?
N1 C4 C11 C12 117.5(6) . . . . ?
O1 C4 C11 C10 177.3(6) . . . . ?
N1 C4 C11 C10 -3.4(6) . . . . ?
N3 C11 C12 N2 -175.4(6) . . . . ?
C10 C11 C12 N2 57.5(8) . . . . ?
C4 C11 C12 N2 -54.4(8) . . . . ?
O1 C4 N1 C5 -178.5(6) . . . . ?
C11 C4 N1 C5 2.2(7) . . . . ?
O1 C4 N1 C3 1.6(11) . . . . ?
C11 C4 N1 C3 -177.7(6) . . . . ?
C10 C5 N1 C4 0.1(8) . . . . ?
C6 C5 N1 C4 177.4(6) . . . . ?
C10 C5 N1 C3 180.0(6) . . . . ?
C6 C5 N1 C3 -2.7(11) . . . . ?
C2 C3 N1 C4 101.9(8) . . . . ?
C2 C3 N1 C5 -78.0(10) . . . . ?
C11 C12 N2 O4 30.2(19) . . . . ?
C11 C12 N2 O4' 103.9(14) . . . . ?
C11 C12 N2 O5 -82(2) . . . . ?
C11 C12 N2 O5' -128.7(13) . . . . ?
O2 C13 N3 C11 11.4(10) . . . . ?
O3 C13 N3 C11 -171.3(5) . . . . ?
C12 C11 N3 C13 165.0(6) . . . . ?
C10 C11 N3 C13 -68.0(7) . . . . ?
C4 C11 N3 C13 44.0(8) . . . . ?
O2 C13 O3 C15 -3.6(9) . . . . ?
N3 C13 O3 C15 179.2(5) . . . . ?
C17 C15 O3 C13 61.5(9) . . . . ?
C16 C15 O3 C13 -177.8(6) . . . . ?
C14 C15 O3 C13 -63.9(7) . . . . ?
O4' N2 O4 O5 143(2) . . . . ?
O5' N2 O4 O5 40.3(14) . . . . ?
C12 N2 O4 O5 -119(2) . . . . ?
O4' N2 O5 O4 -56(3) . . . . ?
O5' N2 O5 O4 -122(2) . . . . ?
C12 N2 O5 O4 131.4(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.959
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.092
_database_code_depnum_ccdc_archive 'CCDC 995338'
