# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013


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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 
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data_13
_database_code_depnum_ccdc_archive 'CCDC 894734'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
((5R,7S)-7-isopropoxy-3-(4-nitrophenyl)-4-oxo-2-
phenyl-2,4,5,7-tetrahydropyrano[3,4-c]pyrazol-5-yl)
methyl acetate
;
_chemical_name_common            
;
((5R,7S)-7-isopropoxy-3-(4-nitrophenyl)-4-oxo-2-phenyl-
2,4,5,7-tetrahydropyrano(3,4-c)pyrazol-5-yl) methyl acetate
;
_chemical_melting_point          200
_chemical_formula_moiety         'C24 H23 N3 O7'
_chemical_formula_sum            'C24 H23 N3 O7'
_chemical_formula_weight         465.45

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   P212121

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


_cell_length_a                   5.9798(9)
_cell_length_b                   14.147(2)
_cell_length_c                   25.909(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2191.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      1.57
_cell_measurement_theta_max      25.49

_exptl_crystal_description       'rectangular block'
_exptl_crystal_colour            Yellowish
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9772
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_process_details   SADABS


_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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 SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11937
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0580
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         25.49
_reflns_number_total             4075
_reflns_number_gt                3287
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXTL (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 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^)+(0.0457P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.8(12)
_refine_ls_number_reflns         4075
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1010
_refine_ls_wR_factor_gt          0.0927
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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 -0.7234(5) 1.22633(19) 0.04076(10) 0.0369(7) Uani 1 1 d . . .
H1A H -0.6827 1.2905 0.0301 0.055 Uiso 1 1 calc R . .
H1B H -0.8848 1.2231 0.0470 0.055 Uiso 1 1 calc R . .
H1C H -0.6826 1.1816 0.0134 0.055 Uiso 1 1 calc R . .
C2 C -0.6016(5) 1.20156(17) 0.08900(10) 0.0320(6) Uani 1 1 d . . .
C3 C -0.2654(5) 1.13585(18) 0.12246(9) 0.0344(7) Uani 1 1 d . . .
H3A H -0.3561 1.1370 0.1544 0.041 Uiso 1 1 calc R . .
H3B H -0.1421 1.1820 0.1263 0.041 Uiso 1 1 calc R . .
C4 C -0.1706(4) 1.03834(17) 0.11436(9) 0.0284(6) Uani 1 1 d . . .
H4 H -0.2942 0.9952 0.1034 0.034 Uiso 1 1 calc R . .
C5 C -0.0717(4) 1.00145(16) 0.16476(9) 0.0262(6) Uani 1 1 d . . .
C6 C 0.1225(4) 0.94077(16) 0.15763(9) 0.0247(6) Uani 1 1 d . . .
C7 C 0.1999(4) 0.91786(16) 0.10816(9) 0.0248(6) Uani 1 1 d . . .
C8 C 0.0984(4) 0.95801(16) 0.06009(9) 0.0256(6) Uani 1 1 d . . .
H8 H 0.2185 0.9707 0.0342 0.031 Uiso 1 1 calc R . .
C9 C -0.1405(4) 0.91325(18) -0.01060(9) 0.0290(6) Uani 1 1 d . . .
H9 H -0.1681 0.9828 -0.0131 0.035 Uiso 1 1 calc R . .
C10 C -0.3584(5) 0.86119(19) -0.01517(10) 0.0390(7) Uani 1 1 d . . .
H10A H -0.4553 0.8780 0.0139 0.059 Uiso 1 1 calc R . .
H10B H -0.3303 0.7929 -0.0148 0.059 Uiso 1 1 calc R . .
H10C H -0.4320 0.8787 -0.0476 0.059 Uiso 1 1 calc R . .
C11 C 0.0210(5) 0.88344(18) -0.05232(9) 0.0341(7) Uani 1 1 d . . .
H11A H 0.0413 0.8147 -0.0511 0.051 Uiso 1 1 calc R . .
H11B H 0.1653 0.9147 -0.0468 0.051 Uiso 1 1 calc R . .
H11C H -0.0388 0.9016 -0.0861 0.051 Uiso 1 1 calc R . .
C12 C 0.2560(4) 0.89073(16) 0.19177(9) 0.0240(6) Uani 1 1 d . . .
C13 C 0.5699(4) 0.77365(16) 0.17629(9) 0.0250(6) Uani 1 1 d . . .
C14 C 0.7578(4) 0.76440(17) 0.14540(9) 0.0270(6) Uani 1 1 d . . .
H14 H 0.7737 0.8017 0.1151 0.032 Uiso 1 1 calc R . .
C15 C 0.9218(5) 0.70040(17) 0.15909(10) 0.0310(6) Uani 1 1 d . . .
H15 H 1.0506 0.6938 0.1379 0.037 Uiso 1 1 calc R . .
C16 C 0.9014(5) 0.64593(18) 0.20303(9) 0.0327(6) Uani 1 1 d . . .
H16 H 1.0164 0.6029 0.2124 0.039 Uiso 1 1 calc R . .
C17 C 0.7119(5) 0.65459(18) 0.23328(10) 0.0325(6) Uani 1 1 d . . .
H17 H 0.6971 0.6169 0.2634 0.039 Uiso 1 1 calc R . .
C18 C 0.5438(5) 0.71726(17) 0.22026(9) 0.0290(6) Uani 1 1 d . . .
H18 H 0.4127 0.7220 0.2408 0.035 Uiso 1 1 calc R . .
C19 C 0.2527(4) 0.89101(16) 0.24890(9) 0.0254(6) Uani 1 1 d . . .
C20 C 0.0585(4) 0.86380(16) 0.27420(9) 0.0270(6) Uani 1 1 d . . .
H20 H -0.0655 0.8414 0.2548 0.032 Uiso 1 1 calc R . .
C21 C 0.0441(5) 0.86905(16) 0.32754(9) 0.0292(6) Uani 1 1 d . . .
H21 H -0.0892 0.8517 0.3451 0.035 Uiso 1 1 calc R . .
C22 C 0.2287(5) 0.90015(17) 0.35417(9) 0.0270(6) Uani 1 1 d . . .
C23 C 0.4269(5) 0.92543(17) 0.33043(9) 0.0283(6) Uani 1 1 d . . .
H23 H 0.5528 0.9448 0.3501 0.034 Uiso 1 1 calc R . .
C24 C 0.4363(4) 0.92164(16) 0.27709(9) 0.0286(6) Uani 1 1 d . . .
H24 H 0.5692 0.9401 0.2597 0.034 Uiso 1 1 calc R . .
N1 N 0.3687(4) 0.85692(14) 0.10984(7) 0.0274(5) Uani 1 1 d . . .
N2 N 0.4012(4) 0.84033(13) 0.16185(7) 0.0253(5) Uani 1 1 d . . .
N3 N 0.2157(4) 0.90728(15) 0.41077(8) 0.0357(6) Uani 1 1 d . . .
O1 O -0.6675(4) 1.21536(15) 0.13198(7) 0.0495(6) Uani 1 1 d . . .
O2 O -0.4032(3) 1.16160(13) 0.07884(7) 0.0416(5) Uani 1 1 d . . .
O3 O -0.0097(3) 1.04439(11) 0.07342(6) 0.0285(4) Uani 1 1 d . . .
O4 O -0.1609(3) 1.01959(12) 0.20625(7) 0.0339(5) Uani 1 1 d . . .
O5 O -0.0513(3) 0.89048(11) 0.04038(6) 0.0291(4) Uani 1 1 d . . .
O6 O 0.0297(4) 0.91848(14) 0.43015(7) 0.0481(6) Uani 1 1 d . . .
O7 O 0.3896(4) 0.90243(14) 0.43538(7) 0.0451(5) Uani 1 1 d . . .

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
C1 0.0377(18) 0.0341(15) 0.0390(16) 0.0021(12) -0.0012(14) 0.0024(14)
C2 0.0332(17) 0.0290(15) 0.0339(16) -0.0060(12) 0.0023(13) 0.0020(13)
C3 0.0390(18) 0.0377(16) 0.0265(14) -0.0006(12) -0.0010(13) 0.0089(14)
C4 0.0286(16) 0.0283(14) 0.0281(14) -0.0011(11) 0.0035(12) 0.0000(12)
C5 0.0282(15) 0.0237(12) 0.0267(14) -0.0004(11) -0.0003(12) -0.0054(12)
C6 0.0263(15) 0.0244(13) 0.0234(13) -0.0006(10) -0.0015(12) -0.0041(11)
C7 0.0248(15) 0.0221(13) 0.0275(14) 0.0012(11) -0.0016(11) -0.0031(12)
C8 0.0269(15) 0.0252(13) 0.0246(13) -0.0026(10) 0.0014(12) -0.0005(12)
C9 0.0343(17) 0.0296(14) 0.0231(13) 0.0016(11) -0.0053(12) 0.0025(12)
C10 0.0382(18) 0.0508(18) 0.0280(14) -0.0027(13) -0.0011(13) -0.0041(15)
C11 0.0437(18) 0.0359(15) 0.0225(14) 0.0002(11) 0.0024(13) 0.0014(13)
C12 0.0227(14) 0.0210(13) 0.0282(14) -0.0021(10) 0.0018(12) -0.0030(11)
C13 0.0277(15) 0.0215(12) 0.0258(13) -0.0025(10) -0.0043(11) 0.0015(12)
C14 0.0289(16) 0.0273(14) 0.0246(13) -0.0028(10) -0.0046(12) -0.0025(12)
C15 0.0288(16) 0.0326(14) 0.0315(15) -0.0085(12) 0.0003(13) 0.0014(12)
C16 0.0381(17) 0.0268(14) 0.0332(15) -0.0032(12) -0.0069(13) 0.0067(13)
C17 0.0433(18) 0.0240(14) 0.0301(14) 0.0021(11) -0.0006(13) -0.0005(13)
C18 0.0324(16) 0.0288(14) 0.0259(13) -0.0023(11) 0.0045(12) -0.0018(12)
C19 0.0290(16) 0.0196(13) 0.0276(14) 0.0006(10) 0.0000(12) 0.0023(11)
C20 0.0258(15) 0.0285(14) 0.0267(13) 0.0021(11) -0.0029(12) -0.0007(12)
C21 0.0291(16) 0.0267(14) 0.0317(15) 0.0019(11) 0.0032(12) 0.0019(12)
C22 0.0362(17) 0.0222(13) 0.0226(13) -0.0007(10) -0.0001(12) 0.0050(12)
C23 0.0302(16) 0.0260(13) 0.0286(14) -0.0016(11) -0.0042(12) 0.0014(12)
C24 0.0279(16) 0.0250(13) 0.0330(15) -0.0009(11) 0.0007(12) 0.0002(12)
N1 0.0313(13) 0.0293(12) 0.0216(11) 0.0025(9) -0.0020(10) -0.0003(10)
N2 0.0277(13) 0.0249(10) 0.0232(11) -0.0001(9) 0.0007(10) 0.0000(10)
N3 0.0430(16) 0.0330(13) 0.0310(13) 0.0005(10) 0.0005(12) -0.0005(12)
O1 0.0412(13) 0.0727(15) 0.0345(11) -0.0087(10) 0.0028(10) 0.0128(12)
O2 0.0434(13) 0.0521(12) 0.0293(10) 0.0039(9) 0.0057(9) 0.0204(10)
O3 0.0336(11) 0.0236(9) 0.0283(10) 0.0018(7) 0.0031(9) 0.0023(8)
O4 0.0339(11) 0.0379(11) 0.0298(10) -0.0009(8) 0.0035(9) 0.0031(9)
O5 0.0348(11) 0.0290(9) 0.0236(9) -0.0012(7) -0.0027(8) -0.0005(9)
O6 0.0497(14) 0.0556(13) 0.0389(12) -0.0040(10) 0.0157(11) 0.0009(11)
O7 0.0557(15) 0.0480(12) 0.0315(11) 0.0012(9) -0.0104(10) -0.0015(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
C1 C2 1.488(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O1 1.197(3) . ?
C2 O2 1.341(3) . ?
C3 O2 1.445(3) . ?
C3 C4 1.506(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O3 1.435(3) . ?
C4 C5 1.526(3) . ?
C4 H4 1.0000 . ?
C5 O4 1.227(3) . ?
C5 C6 1.456(3) . ?
C6 C12 1.386(3) . ?
C6 C7 1.401(3) . ?
C7 N1 1.328(3) . ?
C7 C8 1.497(3) . ?
C8 O5 1.405(3) . ?
C8 O3 1.425(3) . ?
C8 H8 1.0000 . ?
C9 O5 1.460(3) . ?
C9 C10 1.501(4) . ?
C9 C11 1.510(3) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N2 1.365(3) . ?
C12 C19 1.480(3) . ?
C13 C14 1.386(3) . ?
C13 C18 1.400(3) . ?
C13 N2 1.431(3) . ?
C14 C15 1.381(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.382(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.388(3) . ?
C19 C24 1.388(3) . ?
C20 C21 1.387(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.374(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.382(4) . ?
C22 N3 1.472(3) . ?
C23 C24 1.384(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
N1 N2 1.382(3) . ?
N3 O7 1.222(3) . ?
N3 O6 1.231(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 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 122.9(3) . . ?
O1 C2 C1 125.6(3) . . ?
O2 C2 C1 111.5(2) . . ?
O2 C3 C4 109.7(2) . . ?
O2 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
O2 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
O3 C4 C3 107.5(2) . . ?
O3 C4 C5 113.2(2) . . ?
C3 C4 C5 109.88(19) . . ?
O3 C4 H4 108.7 . . ?
C3 C4 H4 108.7 . . ?
C5 C4 H4 108.7 . . ?
O4 C5 C6 125.5(2) . . ?
O4 C5 C4 120.6(2) . . ?
C6 C5 C4 113.7(2) . . ?
C12 C6 C7 106.0(2) . . ?
C12 C6 C5 132.8(2) . . ?
C7 C6 C5 121.1(2) . . ?
N1 C7 C6 111.8(2) . . ?
N1 C7 C8 125.6(2) . . ?
C6 C7 C8 122.6(2) . . ?
O5 C8 O3 112.5(2) . . ?
O5 C8 C7 107.61(19) . . ?
O3 C8 C7 107.92(19) . . ?
O5 C8 H8 109.6 . . ?
O3 C8 H8 109.6 . . ?
C7 C8 H8 109.6 . . ?
O5 C9 C10 106.3(2) . . ?
O5 C9 C11 110.6(2) . . ?
C10 C9 C11 111.2(2) . . ?
O5 C9 H9 109.6 . . ?
C10 C9 H9 109.6 . . ?
C11 C9 H9 109.6 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C6 105.7(2) . . ?
N2 C12 C19 125.3(2) . . ?
C6 C12 C19 129.0(2) . . ?
C14 C13 C18 120.4(2) . . ?
C14 C13 N2 118.9(2) . . ?
C18 C13 N2 120.7(2) . . ?
C15 C14 C13 119.3(2) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 119.4(3) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 121.0(2) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C13 118.9(2) . . ?
C17 C18 H18 120.6 . . ?
C13 C18 H18 120.6 . . ?
C20 C19 C24 120.0(2) . . ?
C20 C19 C12 118.8(2) . . ?
C24 C19 C12 121.1(2) . . ?
C21 C20 C19 120.5(2) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 117.9(2) . . ?
C22 C21 H21 121.1 . . ?
C20 C21 H21 121.1 . . ?
C21 C22 C23 123.2(2) . . ?
C21 C22 N3 118.7(2) . . ?
C23 C22 N3 118.1(2) . . ?
C22 C23 C24 118.0(2) . . ?
C22 C23 H23 121.0 . . ?
C24 C23 H23 121.0 . . ?
C23 C24 C19 120.3(2) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
C7 N1 N2 104.42(18) . . ?
C12 N2 N1 112.1(2) . . ?
C12 N2 C13 130.1(2) . . ?
N1 N2 C13 117.77(19) . . ?
O7 N3 O6 124.3(2) . . ?
O7 N3 C22 118.1(2) . . ?
O6 N3 C22 117.6(2) . . ?
C2 O2 C3 117.21(19) . . ?
C8 O3 C4 115.61(17) . . ?
C8 O5 C9 114.29(18) . . ?


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
O2 C3 C4 O3 69.7(3) . . . . ?
O2 C3 C4 C5 -166.8(2) . . . . ?
O3 C4 C5 O4 156.7(2) . . . . ?
C3 C4 C5 O4 36.5(3) . . . . ?
O3 C4 C5 C6 -26.7(3) . . . . ?
C3 C4 C5 C6 -146.9(2) . . . . ?
O4 C5 C6 C12 -1.0(4) . . . . ?
C4 C5 C6 C12 -177.5(3) . . . . ?
O4 C5 C6 C7 174.3(2) . . . . ?
C4 C5 C6 C7 -2.1(3) . . . . ?
C12 C6 C7 N1 0.7(3) . . . . ?
C5 C6 C7 N1 -175.8(2) . . . . ?
C12 C6 C7 C8 -179.9(2) . . . . ?
C5 C6 C7 C8 3.6(3) . . . . ?
N1 C7 C8 O5 81.0(3) . . . . ?
C6 C7 C8 O5 -98.3(3) . . . . ?
N1 C7 C8 O3 -157.4(2) . . . . ?
C6 C7 C8 O3 23.3(3) . . . . ?
C7 C6 C12 N2 -0.9(3) . . . . ?
C5 C6 C12 N2 175.0(2) . . . . ?
C7 C6 C12 C19 177.8(2) . . . . ?
C5 C6 C12 C19 -6.4(4) . . . . ?
C18 C13 C14 C15 -1.5(4) . . . . ?
N2 C13 C14 C15 179.8(2) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
C14 C15 C16 C17 1.1(4) . . . . ?
C15 C16 C17 C18 -0.3(4) . . . . ?
C16 C17 C18 C13 -1.3(4) . . . . ?
C14 C13 C18 C17 2.2(4) . . . . ?
N2 C13 C18 C17 -179.2(2) . . . . ?
N2 C12 C19 C20 -121.8(3) . . . . ?
C6 C12 C19 C20 59.8(3) . . . . ?
N2 C12 C19 C24 60.9(3) . . . . ?
C6 C12 C19 C24 -117.5(3) . . . . ?
C24 C19 C20 C21 1.5(4) . . . . ?
C12 C19 C20 C21 -175.7(2) . . . . ?
C19 C20 C21 C22 -1.2(3) . . . . ?
C20 C21 C22 C23 -0.6(4) . . . . ?
C20 C21 C22 N3 179.3(2) . . . . ?
C21 C22 C23 C24 1.9(4) . . . . ?
N3 C22 C23 C24 -177.9(2) . . . . ?
C22 C23 C24 C19 -1.6(3) . . . . ?
C20 C19 C24 C23 -0.1(4) . . . . ?
C12 C19 C24 C23 177.1(2) . . . . ?
C6 C7 N1 N2 -0.1(3) . . . . ?
C8 C7 N1 N2 -179.5(2) . . . . ?
C6 C12 N2 N1 0.9(3) . . . . ?
C19 C12 N2 N1 -177.8(2) . . . . ?
C6 C12 N2 C13 -177.1(2) . . . . ?
C19 C12 N2 C13 4.2(4) . . . . ?
C7 N1 N2 C12 -0.5(2) . . . . ?
C7 N1 N2 C13 177.8(2) . . . . ?
C14 C13 N2 C12 -150.3(2) . . . . ?
C18 C13 N2 C12 31.0(4) . . . . ?
C14 C13 N2 N1 31.8(3) . . . . ?
C18 C13 N2 N1 -146.9(2) . . . . ?
C21 C22 N3 O7 155.1(2) . . . . ?
C23 C22 N3 O7 -25.1(3) . . . . ?
C21 C22 N3 O6 -25.5(3) . . . . ?
C23 C22 N3 O6 154.4(2) . . . . ?
O1 C2 O2 C3 -0.7(4) . . . . ?
C1 C2 O2 C3 178.7(2) . . . . ?
C4 C3 O2 C2 135.1(2) . . . . ?
O5 C8 O3 C4 64.1(2) . . . . ?
C7 C8 O3 C4 -54.5(3) . . . . ?
C3 C4 O3 C8 -179.9(2) . . . . ?
C5 C4 O3 C8 58.6(3) . . . . ?
O3 C8 O5 C9 69.7(2) . . . . ?
C7 C8 O5 C9 -171.63(19) . . . . ?
C10 C9 O5 C8 -156.1(2) . . . . ?
C11 C9 O5 C8 83.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.046
#===END