# Electronic Supplementary Material (ESI) for RSC Advances.
# 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.
#
#  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
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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_p21c
#TrackingRef '16239_web_deposit_cif_file_0_HuanmingHuang_1355726599.1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 N O6'
_chemical_formula_weight         405.39

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   P2(1)/c

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

_cell_length_a                   10.2955(19)
_cell_length_b                   21.256(4)
_cell_length_c                   8.8920(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.858(5)
_cell_angle_gamma                90.00
_cell_volume                     1944.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9512
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10676
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3420
_reflns_number_gt                2300
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0921P)²+0.0107P] where P=(Fo²+2Fc²)/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         3420
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1605
_refine_ls_wR_factor_gt          0.1367
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
O1 O 0.36467(16) 0.69537(7) 0.6099(2) 0.0637(5) Uani 1 1 d . . .
O2 O 0.5594(2) 0.72977(9) 0.6844(3) 0.1110(10) Uani 1 1 d . . .
O3 O 0.78697(18) 0.50733(9) 0.4183(2) 0.0766(6) Uani 1 1 d . . .
O4 O 0.80782(15) 0.46018(7) 0.64180(18) 0.0557(5) Uani 1 1 d . . .
O5 O 0.30395(18) 0.61404(7) 0.8780(2) 0.0689(5) Uani 1 1 d . . .
O6 O 0.56566(16) 0.40473(7) 0.7090(2) 0.0636(5) Uani 1 1 d . . .
N1 N 0.62933(18) 0.59936(8) 0.5887(2) 0.0508(5) Uani 1 1 d . . .
C1 C 0.0778(2) 0.43023(12) 1.1354(3) 0.0567(6) Uani 1 1 d . . .
H1 H 0.0298 0.4652 1.1627 0.068 Uiso 1 1 calc R . .
C2 C 0.0413(3) 0.37216(14) 1.1805(3) 0.0671(7) Uani 1 1 d . . .
H2 H -0.0334 0.3676 1.2357 0.080 Uiso 1 1 calc R . .
C3 C 0.1141(3) 0.31902(13) 1.1454(3) 0.0704(8) Uani 1 1 d . . .
H3 H 0.0895 0.2797 1.1807 0.084 Uiso 1 1 calc R . .
C4 C 0.2205(2) 0.32431(11) 1.0602(3) 0.0618(7) Uani 1 1 d . . .
H4 H 0.2675 0.2885 1.0364 0.074 Uiso 1 1 calc R . .
C5 C 0.2610(2) 0.38393(10) 1.0071(3) 0.0463(6) Uani 1 1 d . . .
C6 C 0.1887(2) 0.43797(10) 1.0467(3) 0.0472(6) Uani 1 1 d . . .
C7 C 0.2289(2) 0.49722(10) 0.9924(3) 0.0467(6) Uani 1 1 d . . .
H7 H 0.1834 0.5330 1.0198 0.056 Uiso 1 1 calc R . .
C8 C 0.3319(2) 0.50351(9) 0.9014(2) 0.0425(5) Uani 1 1 d . . .
C9 C 0.4043(2) 0.44901(9) 0.8602(2) 0.0414(5) Uani 1 1 d . . .
C10 C 0.3685(2) 0.39106(10) 0.9147(3) 0.0463(6) Uani 1 1 d . . .
H10 H 0.4166 0.3558 0.8899 0.056 Uiso 1 1 calc R . .
C11 C 0.3641(2) 0.56694(9) 0.8415(3) 0.0478(6) Uani 1 1 d . . .
C12 C 0.4713(2) 0.56931(9) 0.7386(3) 0.0443(5) Uani 1 1 d . . .
C13 C 0.5498(2) 0.51607(10) 0.7072(2) 0.0429(5) Uani 1 1 d . . .
C14 C 0.5144(2) 0.45236(10) 0.7557(3) 0.0438(5) Uani 1 1 d . . .
C15 C 0.5235(2) 0.61957(10) 0.6626(3) 0.0506(6) Uani 1 1 d . . .
C16 C 0.6470(2) 0.53603(10) 0.6142(2) 0.0449(6) Uani 1 1 d . . .
C17 C 0.4853(2) 0.68739(11) 0.6563(3) 0.0613(7) Uani 1 1 d . . .
C18 C 0.3195(3) 0.76026(11) 0.5965(4) 0.0751(9) Uani 1 1 d . . .
H18A H 0.3714 0.7831 0.5256 0.090 Uiso 1 1 calc R . .
H18B H 0.3271 0.7812 0.6933 0.090 Uiso 1 1 calc R . .
C19 C 0.1832(3) 0.75859(13) 0.5435(4) 0.0912(10) Uani 1 1 d . . .
H19A H 0.1762 0.7355 0.4508 0.137 Uiso 1 1 calc R . .
H19B H 0.1524 0.8008 0.5273 0.137 Uiso 1 1 calc R . .
H19C H 0.1318 0.7384 0.6176 0.137 Uiso 1 1 calc R . .
C20 C 0.7533(2) 0.50067(11) 0.5455(3) 0.0504(6) Uani 1 1 d . . .
C21 C 0.8981(3) 0.41563(13) 0.5804(3) 0.0730(8) Uani 1 1 d . . .
H21A H 0.9613 0.4373 0.5205 0.088 Uiso 1 1 calc R . .
H21B H 0.8521 0.3854 0.5168 0.088 Uiso 1 1 calc R . .
C22 C 0.9637(3) 0.38348(16) 0.7084(4) 0.0990(11) Uani 1 1 d . . .
H22A H 1.0086 0.4139 0.7707 0.149 Uiso 1 1 calc R . .
H22B H 1.0249 0.3536 0.6716 0.149 Uiso 1 1 calc R . .
H22C H 0.9004 0.3620 0.7664 0.149 Uiso 1 1 calc R . .
C23 C 0.7100(3) 0.63890(13) 0.4934(3) 0.0709(8) Uani 1 1 d . . .
H23A H 0.6551 0.6660 0.4329 0.106 Uiso 1 1 calc R . .
H23B H 0.7599 0.6126 0.4292 0.106 Uiso 1 1 calc R . .
H23C H 0.7677 0.6639 0.5559 0.106 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
O1 C17 1.307(3) . ?
O1 C18 1.459(3) . ?
O2 C17 1.201(3) . ?
O3 C20 1.202(3) . ?
O4 C20 1.326(3) . ?
O4 C21 1.446(3) . ?
O5 C11 1.226(3) . ?
O6 C14 1.221(3) . ?
N1 C15 1.360(3) . ?
N1 C16 1.376(3) . ?
N1 C23 1.470(3) . ?
C1 C2 1.355(4) . ?
C1 C6 1.418(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.397(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.420(3) . ?
C4 H4 0.9300 . ?
C5 C10 1.408(3) . ?
C5 C6 1.419(3) . ?
C6 C7 1.415(3) . ?
C7 C8 1.361(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.432(3) . ?
C8 C11 1.491(3) . ?
C9 C10 1.378(3) . ?
C9 C14 1.491(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.457(3) . ?
C12 C15 1.382(3) . ?
C12 C13 1.424(3) . ?
C13 C16 1.384(3) . ?
C13 C14 1.471(3) . ?
C15 C17 1.495(3) . ?
C16 C20 1.476(3) . ?
C18 C19 1.466(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 C22 1.473(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C17 O1 C18 116.46(18) . . ?
C20 O4 C21 116.5(2) . . ?
C15 N1 C16 109.46(19) . . ?
C15 N1 C23 125.1(2) . . ?
C16 N1 C23 125.5(2) . . ?
C2 C1 C6 120.4(2) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C1 C2 C3 121.0(3) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C10 C5 C6 119.1(2) . . ?
C10 C5 C4 122.3(2) . . ?
C6 C5 C4 118.6(2) . . ?
C7 C6 C1 122.8(2) . . ?
C7 C6 C5 118.3(2) . . ?
C1 C6 C5 118.8(2) . . ?
C8 C7 C6 122.1(2) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C9 119.7(2) . . ?
C7 C8 C11 119.21(19) . . ?
C9 C8 C11 121.1(2) . . ?
C10 C9 C8 119.1(2) . . ?
C10 C9 C14 118.63(19) . . ?
C8 C9 C14 122.26(19) . . ?
C9 C10 C5 121.7(2) . . ?
C9 C10 H10 119.1 . . ?
C5 C10 H10 119.1 . . ?
O5 C11 C12 122.5(2) . . ?
O5 C11 C8 121.5(2) . . ?
C12 C11 C8 115.95(18) . . ?
C15 C12 C13 106.6(2) . . ?
C15 C12 C11 130.4(2) . . ?
C13 C12 C11 122.85(19) . . ?
C16 C13 C12 107.42(19) . . ?
C16 C13 C14 130.4(2) . . ?
C12 C13 C14 121.8(2) . . ?
O6 C14 C13 123.4(2) . . ?
O6 C14 C9 121.21(19) . . ?
C13 C14 C9 115.32(18) . . ?
N1 C15 C12 108.81(19) . . ?
N1 C15 C17 120.0(2) . . ?
C12 C15 C17 131.1(2) . . ?
N1 C16 C13 107.70(19) . . ?
N1 C16 C20 121.7(2) . . ?
C13 C16 C20 130.6(2) . . ?
O2 C17 O1 123.9(2) . . ?
O2 C17 C15 123.5(2) . . ?
O1 C17 C15 112.52(19) . . ?
O1 C18 C19 107.6(2) . . ?
O1 C18 H18A 110.2 . . ?
C19 C18 H18A 110.2 . . ?
O1 C18 H18B 110.2 . . ?
C19 C18 H18B 110.2 . . ?
H18A C18 H18B 108.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 O4 123.7(2) . . ?
O3 C20 C16 124.7(2) . . ?
O4 C20 C16 111.6(2) . . ?
O4 C21 C22 107.3(2) . . ?
O4 C21 H21A 110.3 . . ?
C22 C21 H21A 110.3 . . ?
O4 C21 H21B 110.3 . . ?
C22 C21 H21B 110.3 . . ?
H21A C21 H21B 108.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C6 C1 C2 C3 2.2(4) . . . . ?
C1 C2 C3 C4 -2.5(4) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C3 C4 C5 C10 -178.0(2) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C2 C1 C6 C7 177.9(2) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
C10 C5 C6 C7 -0.6(3) . . . . ?
C4 C5 C6 C7 -179.50(19) . . . . ?
C10 C5 C6 C1 177.80(19) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
C1 C6 C7 C8 -176.8(2) . . . . ?
C5 C6 C7 C8 1.6(3) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C6 C7 C8 C11 176.58(17) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C11 C8 C9 C10 -178.03(18) . . . . ?
C7 C8 C9 C14 177.29(18) . . . . ?
C11 C8 C9 C14 -0.3(3) . . . . ?
C8 C9 C10 C5 1.4(3) . . . . ?
C14 C9 C10 C5 -176.42(18) . . . . ?
C6 C5 C10 C9 -0.9(3) . . . . ?
C4 C5 C10 C9 178.0(2) . . . . ?
C7 C8 C11 O5 3.6(3) . . . . ?
C9 C8 C11 O5 -178.9(2) . . . . ?
C7 C8 C11 C12 -176.87(18) . . . . ?
C9 C8 C11 C12 0.7(3) . . . . ?
O5 C11 C12 C15 -1.6(4) . . . . ?
C8 C11 C12 C15 178.8(2) . . . . ?
O5 C11 C12 C13 173.7(2) . . . . ?
C8 C11 C12 C13 -5.9(3) . . . . ?
C15 C12 C13 C16 0.4(2) . . . . ?
C11 C12 C13 C16 -175.87(19) . . . . ?
C15 C12 C13 C14 -172.95(18) . . . . ?
C11 C12 C13 C14 10.8(3) . . . . ?
C16 C13 C14 O6 -4.9(3) . . . . ?
C12 C13 C14 O6 166.7(2) . . . . ?
C16 C13 C14 C9 178.78(19) . . . . ?
C12 C13 C14 C9 -9.6(3) . . . . ?
C10 C9 C14 O6 5.9(3) . . . . ?
C8 C9 C14 O6 -171.89(19) . . . . ?
C10 C9 C14 C13 -177.75(17) . . . . ?
C8 C9 C14 C13 4.5(3) . . . . ?
C16 N1 C15 C12 0.5(2) . . . . ?
C23 N1 C15 C12 179.0(2) . . . . ?
C16 N1 C15 C17 178.4(2) . . . . ?
C23 N1 C15 C17 -3.1(3) . . . . ?
C13 C12 C15 N1 -0.5(2) . . . . ?
C11 C12 C15 N1 175.3(2) . . . . ?
C13 C12 C15 C17 -178.1(2) . . . . ?
C11 C12 C15 C17 -2.2(4) . . . . ?
C15 N1 C16 C13 -0.3(2) . . . . ?
C23 N1 C16 C13 -178.8(2) . . . . ?
C15 N1 C16 C20 178.72(19) . . . . ?
C23 N1 C16 C20 0.2(3) . . . . ?
C12 C13 C16 N1 -0.1(2) . . . . ?
C14 C13 C16 N1 172.5(2) . . . . ?
C12 C13 C16 C20 -178.9(2) . . . . ?
C14 C13 C16 C20 -6.4(4) . . . . ?
C18 O1 C17 O2 -1.6(4) . . . . ?
C18 O1 C17 C15 -178.5(2) . . . . ?
N1 C15 C17 O2 -51.3(4) . . . . ?
C12 C15 C17 O2 126.0(3) . . . . ?
N1 C15 C17 O1 125.6(2) . . . . ?
C12 C15 C17 O1 -57.1(3) . . . . ?
C17 O1 C18 C19 180.0(3) . . . . ?
C21 O4 C20 O3 -9.9(3) . . . . ?
C21 O4 C20 C16 170.03(19) . . . . ?
N1 C16 C20 O3 -40.8(3) . . . . ?
C13 C16 C20 O3 137.9(3) . . . . ?
N1 C16 C20 O4 139.2(2) . . . . ?
C13 C16 C20 O4 -42.1(3) . . . . ?
C20 O4 C21 C22 170.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.046


_database_code_depnum_ccdc_archive 'CCDC 915882'
