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


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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 
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#  except for the purpose of generating routine backup copies 
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data_p21c
_database_code_depnum_ccdc_archive 'CCDC 889553'
#TrackingRef '3p.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H23 N O5'
_chemical_formula_weight         417.44

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                   8.436(4)
_cell_length_b                   14.318(7)
_cell_length_c                   17.219(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.109(5)
_cell_angle_gamma                90.00
_cell_volume                     2076.7(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2548
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      24.70

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9789
_exptl_absorpt_correction_T_max  0.9825
_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       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9753
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3823
_reflns_number_gt                2489
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.1000P)^2^+0.3116P] 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         3823
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1655
_refine_ls_wR_factor_gt          0.1341
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_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 0.4612(3) 0.43823(16) 0.70935(12) 0.0329(5) Uani 1 1 d . . .
C2 C 0.6240(3) 0.41392(16) 0.69638(12) 0.0329(5) Uani 1 1 d . . .
C3 C 0.6959(3) 0.32728(19) 0.69153(14) 0.0475(7) Uani 1 1 d . . .
H3 H 0.6373 0.2726 0.6953 0.057 Uiso 1 1 calc R . .
C4 C 0.8553(4) 0.3242(2) 0.68103(17) 0.0560(8) Uani 1 1 d . . .
H4 H 0.9065 0.2669 0.6781 0.067 Uiso 1 1 calc R . .
C5 C 0.9411(3) 0.4065(2) 0.67463(15) 0.0524(7) Uani 1 1 d . . .
H5 H 1.0495 0.4027 0.6677 0.063 Uiso 1 1 calc R . .
C6 C 0.8720(3) 0.49312(18) 0.67823(13) 0.0399(6) Uani 1 1 d . . .
H6 H 0.9311 0.5474 0.6730 0.048 Uiso 1 1 calc R . .
C7 C 0.7098(3) 0.49665(16) 0.69008(11) 0.0315(5) Uani 1 1 d . . .
C8 C 0.4570(3) 0.54674(16) 0.71786(12) 0.0305(5) Uani 1 1 d . . .
C9 C 0.4217(3) 0.56886(15) 0.80173(12) 0.0301(5) Uani 1 1 d . . .
C10 C 0.5373(3) 0.59800(17) 0.85491(13) 0.0367(6) Uani 1 1 d . . .
H10 H 0.6396 0.6083 0.8392 0.044 Uiso 1 1 calc R . .
C11 C 0.5043(3) 0.61242(18) 0.93225(13) 0.0400(6) Uani 1 1 d . . .
H11 H 0.5841 0.6328 0.9676 0.048 Uiso 1 1 calc R . .
C12 C 0.3548(3) 0.59677(17) 0.95643(12) 0.0350(6) Uani 1 1 d . . .
C13 C 0.2364(3) 0.56597(16) 0.90244(13) 0.0345(6) Uani 1 1 d . . .
C14 C 0.2696(3) 0.55199(16) 0.82626(12) 0.0329(5) Uani 1 1 d . . .
H14 H 0.1902 0.5312 0.7908 0.040 Uiso 1 1 calc R . .
C15 C 0.4212(4) 0.6435(2) 1.08639(14) 0.0562(8) Uani 1 1 d . . .
H15A H 0.5090 0.6010 1.0919 0.084 Uiso 1 1 calc R . .
H15B H 0.3728 0.6496 1.1353 0.084 Uiso 1 1 calc R . .
H15C H 0.4584 0.7035 1.0703 0.084 Uiso 1 1 calc R . .
C16 C -0.0347(3) 0.5247(2) 0.88042(15) 0.0523(7) Uani 1 1 d . . .
H16A H -0.0572 0.5738 0.8435 0.078 Uiso 1 1 calc R . .
H16B H -0.1271 0.5127 0.9091 0.078 Uiso 1 1 calc R . .
H16C H -0.0061 0.4690 0.8534 0.078 Uiso 1 1 calc R . .
C17 C 0.6725(3) 0.66938(16) 0.69395(13) 0.0408(6) Uani 1 1 d . . .
H17A H 0.7531 0.6789 0.7355 0.049 Uiso 1 1 calc R . .
H17B H 0.5850 0.7113 0.7029 0.049 Uiso 1 1 calc R . .
C18 C 0.7412(3) 0.69456(16) 0.61750(13) 0.0370(6) Uani 1 1 d . . .
C19 C 0.6944(3) 0.65265(19) 0.54867(14) 0.0477(7) Uani 1 1 d . . .
H19 H 0.6185 0.6055 0.5482 0.057 Uiso 1 1 calc R . .
C20 C 0.7581(4) 0.6793(2) 0.48006(16) 0.0600(8) Uani 1 1 d . . .
H20 H 0.7249 0.6503 0.4337 0.072 Uiso 1 1 calc R . .
C21 C 0.8690(4) 0.7477(2) 0.48004(17) 0.0622(9) Uani 1 1 d . . .
H21 H 0.9112 0.7659 0.4336 0.075 Uiso 1 1 calc R . .
C22 C 0.9186(4) 0.7898(2) 0.54761(18) 0.0669(9) Uani 1 1 d . . .
H22 H 0.9954 0.8364 0.5475 0.080 Uiso 1 1 calc R . .
C23 C 0.8550(3) 0.7633(2) 0.61671(16) 0.0553(8) Uani 1 1 d . . .
H23 H 0.8894 0.7923 0.6629 0.066 Uiso 1 1 calc R . .
C24 C 0.3341(3) 0.58930(18) 0.65966(13) 0.0387(6) Uani 1 1 d . . .
C25 C 0.2346(4) 0.5895(3) 0.52944(17) 0.0809(11) Uani 1 1 d . . .
H25A H 0.1263 0.5769 0.5405 0.121 Uiso 1 1 calc R . .
H25B H 0.2575 0.5613 0.4807 0.121 Uiso 1 1 calc R . .
H25C H 0.2505 0.6557 0.5265 0.121 Uiso 1 1 calc R . .
N1 N 0.6159(2) 0.57381(13) 0.69726(10) 0.0333(5) Uani 1 1 d . . .
O1 O 0.3470(2) 0.38788(12) 0.71577(10) 0.0466(5) Uani 1 1 d . . .
O2 O 0.3081(2) 0.60892(13) 1.02986(9) 0.0504(5) Uani 1 1 d . . .
O3 O 0.09204(19) 0.55173(14) 0.93217(9) 0.0491(5) Uani 1 1 d . . .
O4 O 0.2464(3) 0.65051(17) 0.67321(11) 0.0854(8) Uani 1 1 d . . .
O5 O 0.3397(2) 0.55080(15) 0.59095(10) 0.0631(6) 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 0.0354(14) 0.0392(14) 0.0248(11) 0.0007(9) 0.0079(9) -0.0010(11)
C2 0.0335(13) 0.0372(13) 0.0289(11) -0.0008(9) 0.0096(9) 0.0036(11)
C3 0.0549(18) 0.0414(15) 0.0477(15) 0.0019(11) 0.0169(13) 0.0058(13)
C4 0.0550(19) 0.0496(18) 0.0648(18) -0.0007(13) 0.0159(14) 0.0179(15)
C5 0.0332(15) 0.074(2) 0.0512(16) -0.0052(14) 0.0113(12) 0.0141(15)
C6 0.0312(13) 0.0520(16) 0.0371(12) -0.0044(11) 0.0085(10) -0.0024(12)
C7 0.0293(13) 0.0418(14) 0.0240(10) -0.0022(9) 0.0067(9) 0.0008(11)
C8 0.0276(12) 0.0355(13) 0.0292(11) -0.0008(9) 0.0077(9) -0.0005(10)
C9 0.0292(13) 0.0327(13) 0.0289(11) 0.0011(9) 0.0071(9) 0.0035(10)
C10 0.0283(13) 0.0466(15) 0.0357(12) 0.0027(10) 0.0070(10) -0.0024(11)
C11 0.0356(14) 0.0510(16) 0.0334(12) -0.0026(10) 0.0004(10) -0.0056(12)
C12 0.0367(14) 0.0418(14) 0.0271(11) -0.0012(9) 0.0075(10) 0.0021(11)
C13 0.0277(13) 0.0426(14) 0.0342(12) -0.0014(10) 0.0103(10) -0.0004(11)
C14 0.0267(12) 0.0421(14) 0.0303(11) -0.0032(10) 0.0042(9) -0.0014(11)
C15 0.071(2) 0.0645(19) 0.0328(13) -0.0096(12) 0.0020(13) -0.0118(16)
C16 0.0317(14) 0.079(2) 0.0470(15) -0.0005(13) 0.0098(11) -0.0060(14)
C17 0.0499(16) 0.0349(14) 0.0389(13) -0.0041(10) 0.0130(11) -0.0064(12)
C18 0.0386(14) 0.0340(13) 0.0396(13) 0.0017(10) 0.0136(10) 0.0005(11)
C19 0.0566(18) 0.0447(16) 0.0430(14) -0.0026(11) 0.0145(12) -0.0101(13)
C20 0.083(2) 0.0573(19) 0.0418(15) -0.0036(13) 0.0173(15) 0.0019(17)
C21 0.085(2) 0.0530(19) 0.0527(17) 0.0073(14) 0.0386(16) 0.0015(17)
C22 0.074(2) 0.059(2) 0.070(2) 0.0026(16) 0.0316(17) -0.0228(17)
C23 0.0621(19) 0.0546(18) 0.0505(15) -0.0033(13) 0.0157(13) -0.0208(15)
C24 0.0403(15) 0.0441(15) 0.0327(12) 0.0000(10) 0.0105(10) 0.0021(12)
C25 0.095(3) 0.102(3) 0.0432(16) -0.0032(16) -0.0203(17) 0.028(2)
N1 0.0320(11) 0.0314(11) 0.0381(10) -0.0002(8) 0.0156(8) -0.0033(9)
O1 0.0397(10) 0.0450(11) 0.0562(11) -0.0024(8) 0.0133(8) -0.0109(9)
O2 0.0487(11) 0.0737(13) 0.0296(9) -0.0104(8) 0.0096(8) -0.0088(9)
O3 0.0299(10) 0.0819(14) 0.0369(9) -0.0094(8) 0.0139(7) -0.0066(9)
O4 0.1132(19) 0.0961(18) 0.0461(11) -0.0045(11) -0.0038(12) 0.0682(16)
O5 0.0731(14) 0.0778(15) 0.0368(10) -0.0130(9) -0.0106(9) 0.0275(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 O1 1.213(3) . ?
C1 C2 1.446(3) . ?
C1 C8 1.561(3) . ?
C2 C3 1.386(3) . ?
C2 C7 1.395(3) . ?
C3 C4 1.367(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.396(3) . ?
C6 H6 0.9300 . ?
C7 N1 1.368(3) . ?
C8 N1 1.458(3) . ?
C8 C9 1.523(3) . ?
C8 C24 1.529(3) . ?
C9 C10 1.366(3) . ?
C9 C14 1.394(3) . ?
C10 C11 1.391(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.368(3) . ?
C11 H11 0.9300 . ?
C12 O2 1.356(3) . ?
C12 C13 1.398(3) . ?
C13 O3 1.362(3) . ?
C13 C14 1.371(3) . ?
C14 H14 0.9300 . ?
C15 O2 1.415(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O3 1.408(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 N1 1.451(3) . ?
C17 C18 1.511(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.367(3) . ?
C18 C23 1.375(4) . ?
C19 C20 1.378(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.355(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.356(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.384(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 O4 1.179(3) . ?
C24 O5 1.308(3) . ?
C25 O5 1.454(3) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
O1 C1 C2 129.6(2) . . ?
O1 C1 C8 124.1(2) . . ?
C2 C1 C8 106.28(19) . . ?
C3 C2 C7 121.7(2) . . ?
C3 C2 C1 130.4(2) . . ?
C7 C2 C1 108.0(2) . . ?
C4 C3 C2 118.3(3) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 122.5(3) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C5 C6 C7 117.5(2) . . ?
C5 C6 H6 121.3 . . ?
C7 C6 H6 121.3 . . ?
N1 C7 C2 111.9(2) . . ?
N1 C7 C6 128.2(2) . . ?
C2 C7 C6 119.8(2) . . ?
N1 C8 C9 113.89(18) . . ?
N1 C8 C24 109.54(18) . . ?
C9 C8 C24 112.21(18) . . ?
N1 C8 C1 102.48(17) . . ?
C9 C8 C1 107.61(17) . . ?
C24 C8 C1 110.67(18) . . ?
C10 C9 C14 119.0(2) . . ?
C10 C9 C8 122.0(2) . . ?
C14 C9 C8 118.79(19) . . ?
C9 C10 C11 121.0(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
O2 C12 C11 125.6(2) . . ?
O2 C12 C13 115.3(2) . . ?
C11 C12 C13 119.1(2) . . ?
O3 C13 C14 124.8(2) . . ?
O3 C13 C12 114.72(19) . . ?
C14 C13 C12 120.5(2) . . ?
C13 C14 C9 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 C18 113.69(18) . . ?
N1 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
N1 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C23 118.3(2) . . ?
C19 C18 C17 123.0(2) . . ?
C23 C18 C17 118.7(2) . . ?
C18 C19 C20 120.9(3) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C21 C20 C19 120.1(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.1(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C23 120.0(3) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C18 C23 C22 120.5(3) . . ?
C18 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
O4 C24 O5 123.1(2) . . ?
O4 C24 C8 125.3(2) . . ?
O5 C24 C8 111.6(2) . . ?
O5 C25 H25A 109.5 . . ?
O5 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O5 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C7 N1 C17 124.4(2) . . ?
C7 N1 C8 110.57(18) . . ?
C17 N1 C8 124.67(18) . . ?
C12 O2 C15 117.9(2) . . ?
C13 O3 C16 117.83(18) . . ?
C24 O5 C25 116.6(2) . . ?

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
O1 C1 C2 C3 -3.6(4) . . . . ?
C8 C1 C2 C3 173.9(2) . . . . ?
O1 C1 C2 C7 177.6(2) . . . . ?
C8 C1 C2 C7 -4.9(2) . . . . ?
C7 C2 C3 C4 0.6(4) . . . . ?
C1 C2 C3 C4 -178.1(2) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C4 C5 C6 C7 1.1(4) . . . . ?
C3 C2 C7 N1 -179.4(2) . . . . ?
C1 C2 C7 N1 -0.5(2) . . . . ?
C3 C2 C7 C6 0.3(3) . . . . ?
C1 C2 C7 C6 179.24(18) . . . . ?
C5 C6 C7 N1 178.6(2) . . . . ?
C5 C6 C7 C2 -1.1(3) . . . . ?
O1 C1 C8 N1 -174.3(2) . . . . ?
C2 C1 C8 N1 8.0(2) . . . . ?
O1 C1 C8 C9 65.3(3) . . . . ?
C2 C1 C8 C9 -112.33(19) . . . . ?
O1 C1 C8 C24 -57.6(3) . . . . ?
C2 C1 C8 C24 124.75(19) . . . . ?
N1 C8 C9 C10 -9.4(3) . . . . ?
C24 C8 C9 C10 -134.6(2) . . . . ?
C1 C8 C9 C10 103.4(2) . . . . ?
N1 C8 C9 C14 175.56(19) . . . . ?
C24 C8 C9 C14 50.4(3) . . . . ?
C1 C8 C9 C14 -71.6(3) . . . . ?
C14 C9 C10 C11 -1.1(3) . . . . ?
C8 C9 C10 C11 -176.1(2) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C10 C11 C12 O2 -179.5(2) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
O2 C12 C13 O3 -0.7(3) . . . . ?
C11 C12 C13 O3 179.5(2) . . . . ?
O2 C12 C13 C14 179.5(2) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
O3 C13 C14 C9 179.9(2) . . . . ?
C12 C13 C14 C9 -0.3(3) . . . . ?
C10 C9 C14 C13 1.0(3) . . . . ?
C8 C9 C14 C13 176.2(2) . . . . ?
N1 C17 C18 C19 28.0(3) . . . . ?
N1 C17 C18 C23 -152.7(2) . . . . ?
C23 C18 C19 C20 -0.7(4) . . . . ?
C17 C18 C19 C20 178.6(3) . . . . ?
C18 C19 C20 C21 0.2(4) . . . . ?
C19 C20 C21 C22 0.5(5) . . . . ?
C20 C21 C22 C23 -0.5(5) . . . . ?
C19 C18 C23 C22 0.7(4) . . . . ?
C17 C18 C23 C22 -178.7(3) . . . . ?
C21 C22 C23 C18 -0.1(5) . . . . ?
N1 C8 C24 O4 -109.2(3) . . . . ?
C9 C8 C24 O4 18.3(4) . . . . ?
C1 C8 C24 O4 138.5(3) . . . . ?
N1 C8 C24 O5 69.3(3) . . . . ?
C9 C8 C24 O5 -163.2(2) . . . . ?
C1 C8 C24 O5 -43.0(3) . . . . ?
C2 C7 N1 C17 179.37(19) . . . . ?
C6 C7 N1 C17 -0.3(3) . . . . ?
C2 C7 N1 C8 6.2(2) . . . . ?
C6 C7 N1 C8 -173.5(2) . . . . ?
C18 C17 N1 C7 61.2(3) . . . . ?
C18 C17 N1 C8 -126.6(2) . . . . ?
C9 C8 N1 C7 107.3(2) . . . . ?
C24 C8 N1 C7 -126.1(2) . . . . ?
C1 C8 N1 C7 -8.6(2) . . . . ?
C9 C8 N1 C17 -65.8(3) . . . . ?
C24 C8 N1 C17 60.7(3) . . . . ?
C1 C8 N1 C17 178.25(19) . . . . ?
C11 C12 O2 C15 2.1(4) . . . . ?
C13 C12 O2 C15 -177.6(2) . . . . ?
C14 C13 O3 C16 -3.0(4) . . . . ?
C12 C13 O3 C16 177.2(2) . . . . ?
O4 C24 O5 C25 2.1(4) . . . . ?
C8 C24 O5 C25 -176.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.046


data_5i
_database_code_depnum_ccdc_archive 'CCDC 889554'
#TrackingRef '5i.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H23 N O3'
_chemical_formula_weight         385.44

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                   10.343(10)
_cell_length_b                   9.614(9)
_cell_length_c                   20.75(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.745(11)
_cell_angle_gamma                90.00
_cell_volume                     2020(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2626
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      23.54

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9692
_exptl_absorpt_correction_T_max  0.9779
_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       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9053
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0694
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3723
_reflns_number_gt                2285
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.1464P)^2^+3.2045P] 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     SHELXL
_refine_ls_extinction_coef       0.030(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3723
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1349
_refine_ls_R_factor_gt           0.0901
_refine_ls_wR_factor_ref         0.3272
_refine_ls_wR_factor_gt          0.2854
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_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 0.7367(5) 0.6920(5) 0.1291(2) 0.0428(12) Uani 1 1 d . . .
C2 C 0.6059(5) 0.6788(6) 0.0962(3) 0.0556(14) Uani 1 1 d . . .
H2 H 0.5494 0.6205 0.1132 0.067 Uiso 1 1 calc R . .
C3 C 0.5590(5) 0.7507(7) 0.0389(3) 0.0651(16) Uani 1 1 d . . .
H3 H 0.4716 0.7395 0.0174 0.078 Uiso 1 1 calc R . .
C4 C 0.6389(6) 0.8380(7) 0.0134(3) 0.0643(16) Uani 1 1 d . . .
H4 H 0.6052 0.8885 -0.0245 0.077 Uiso 1 1 calc R . .
C5 C 0.7704(5) 0.8518(6) 0.0438(2) 0.0511(13) Uani 1 1 d . . .
H5 H 0.8246 0.9116 0.0261 0.061 Uiso 1 1 calc R . .
C6 C 0.8219(5) 0.7776(5) 0.1003(2) 0.0413(11) Uani 1 1 d . . .
C7 C 0.9603(5) 0.7839(5) 0.1340(2) 0.0428(11) Uani 1 1 d . . .
C8 C 0.9959(5) 0.7385(5) 0.1960(2) 0.0461(12) Uani 1 1 d . . .
H8 H 1.0840 0.7467 0.2169 0.055 Uiso 1 1 calc R . .
C9 C 0.9024(5) 0.6760(5) 0.2328(2) 0.0450(12) Uani 1 1 d . . .
H9 H 0.9469 0.5962 0.2571 0.054 Uiso 1 1 calc R . .
C10 C 0.7004(6) 0.5358(6) 0.2158(2) 0.0548(14) Uani 1 1 d . . .
H10A H 0.6176 0.5847 0.2137 0.066 Uiso 1 1 calc R . .
H10B H 0.7402 0.5227 0.2620 0.066 Uiso 1 1 calc R . .
C11 C 0.6715(5) 0.3953(5) 0.1844(2) 0.0470(12) Uani 1 1 d . . .
C12 C 0.7570(6) 0.3321(6) 0.1501(3) 0.0564(14) Uani 1 1 d . . .
H12 H 0.8322 0.3790 0.1438 0.068 Uiso 1 1 calc R . .
C13 C 0.7311(6) 0.1993(7) 0.1252(3) 0.0678(17) Uani 1 1 d . . .
H13 H 0.7891 0.1571 0.1023 0.081 Uiso 1 1 calc R . .
C14 C 0.6216(7) 0.1301(7) 0.1338(3) 0.0713(18) Uani 1 1 d . . .
H14 H 0.6045 0.0408 0.1170 0.086 Uiso 1 1 calc R . .
C15 C 0.5369(7) 0.1923(8) 0.1673(3) 0.080(2) Uani 1 1 d . . .
H15 H 0.4618 0.1449 0.1733 0.096 Uiso 1 1 calc R . .
C16 C 0.5607(6) 0.3232(7) 0.1922(3) 0.0642(16) Uani 1 1 d . . .
H16 H 0.5015 0.3643 0.2146 0.077 Uiso 1 1 calc R . .
C17 C 0.8661(5) 0.7755(5) 0.2831(2) 0.0410(11) Uani 1 1 d . . .
C18 C 0.8052(5) 0.8998(5) 0.2642(2) 0.0480(12) Uani 1 1 d . . .
H18 H 0.7873 0.9238 0.2198 0.058 Uiso 1 1 calc R . .
C19 C 0.7699(5) 0.9893(6) 0.3088(2) 0.0528(13) Uani 1 1 d . . .
H19 H 0.7280 1.0727 0.2948 0.063 Uiso 1 1 calc R . .
C20 C 0.7971(5) 0.9552(6) 0.3754(2) 0.0504(13) Uani 1 1 d . . .
C21 C 0.8597(6) 0.8322(6) 0.3955(2) 0.0548(14) Uani 1 1 d . . .
H21 H 0.8794 0.8090 0.4400 0.066 Uiso 1 1 calc R . .
C22 C 0.8933(5) 0.7428(6) 0.3494(2) 0.0480(12) Uani 1 1 d . . .
H22 H 0.9350 0.6591 0.3632 0.058 Uiso 1 1 calc R . .
C23 C 0.7850(8) 1.0225(8) 0.4848(3) 0.090(2) Uani 1 1 d . . .
H23A H 0.7373 0.9408 0.4930 0.135 Uiso 1 1 calc R . .
H23B H 0.7578 1.1000 0.5080 0.135 Uiso 1 1 calc R . .
H23C H 0.8780 1.0071 0.4999 0.135 Uiso 1 1 calc R . .
C24 C 1.0630(5) 0.8308(5) 0.0984(2) 0.0471(12) Uani 1 1 d . . .
C25 C 1.2862(6) 0.8910(8) 0.1095(3) 0.080(2) Uani 1 1 d . . .
H25A H 1.2835 0.8313 0.0722 0.120 Uiso 1 1 calc R . .
H25B H 1.3667 0.8750 0.1410 0.120 Uiso 1 1 calc R . .
H25C H 1.2826 0.9863 0.0955 0.120 Uiso 1 1 calc R . .
N1 N 0.7870(4) 0.6223(4) 0.18627(18) 0.0480(11) Uani 1 1 d . . .
O1 O 1.0501(4) 0.8359(5) 0.04014(19) 0.0785(14) Uani 1 1 d . . .
O2 O 1.1760(4) 0.8615(4) 0.13909(18) 0.0601(11) Uani 1 1 d . . .
O3 O 0.7582(5) 1.0514(5) 0.41594(19) 0.0785(14) 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 0.054(3) 0.042(3) 0.033(2) -0.003(2) 0.010(2) -0.001(2)
C2 0.052(3) 0.065(4) 0.053(3) -0.006(3) 0.017(2) -0.004(3)
C3 0.047(3) 0.089(5) 0.053(3) 0.000(3) -0.002(2) 0.004(3)
C4 0.058(3) 0.085(5) 0.047(3) 0.014(3) 0.004(2) 0.006(3)
C5 0.057(3) 0.056(3) 0.041(3) 0.007(2) 0.012(2) 0.000(2)
C6 0.052(3) 0.039(3) 0.033(2) -0.002(2) 0.0081(19) 0.000(2)
C7 0.049(3) 0.045(3) 0.034(2) -0.005(2) 0.007(2) 0.001(2)
C8 0.045(3) 0.051(3) 0.040(3) 0.000(2) 0.005(2) 0.001(2)
C9 0.055(3) 0.043(3) 0.035(2) 0.004(2) 0.005(2) 0.003(2)
C10 0.070(3) 0.053(3) 0.044(3) 0.004(2) 0.020(2) -0.008(3)
C11 0.051(3) 0.052(3) 0.036(2) 0.008(2) 0.002(2) -0.006(2)
C12 0.057(3) 0.055(4) 0.055(3) -0.002(3) 0.007(3) -0.003(3)
C13 0.067(4) 0.063(4) 0.068(4) -0.009(3) 0.000(3) 0.013(3)
C14 0.090(5) 0.051(4) 0.062(4) -0.003(3) -0.013(3) -0.010(3)
C15 0.082(5) 0.081(5) 0.073(4) -0.002(4) 0.005(4) -0.038(4)
C16 0.063(3) 0.070(4) 0.061(3) -0.003(3) 0.014(3) -0.013(3)
C17 0.048(3) 0.038(3) 0.035(2) 0.005(2) 0.0036(19) -0.006(2)
C18 0.067(3) 0.046(3) 0.030(2) 0.006(2) 0.006(2) 0.001(2)
C19 0.066(3) 0.041(3) 0.050(3) 0.004(2) 0.009(2) 0.001(2)
C20 0.068(3) 0.043(3) 0.043(3) -0.006(2) 0.017(2) -0.005(2)
C21 0.074(4) 0.056(4) 0.033(2) 0.005(2) 0.008(2) -0.004(3)
C22 0.057(3) 0.046(3) 0.038(2) 0.005(2) 0.004(2) 0.002(2)
C23 0.142(7) 0.085(5) 0.048(4) -0.007(3) 0.034(4) 0.017(5)
C24 0.051(3) 0.047(3) 0.044(3) -0.004(2) 0.010(2) 0.000(2)
C25 0.067(4) 0.096(5) 0.082(4) -0.011(4) 0.027(3) -0.032(4)
N1 0.064(3) 0.045(2) 0.034(2) 0.0013(18) 0.0090(18) -0.013(2)
O1 0.065(2) 0.129(4) 0.045(2) 0.011(2) 0.0187(18) -0.006(2)
O2 0.056(2) 0.075(3) 0.053(2) -0.0152(19) 0.0181(17) -0.0204(19)
O3 0.128(4) 0.062(3) 0.052(2) -0.005(2) 0.033(2) 0.011(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 N1 1.370(6) . ?
C1 C2 1.391(7) . ?
C1 C6 1.423(7) . ?
C2 C3 1.375(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.358(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.461(7) . ?
C7 C8 1.337(6) . ?
C7 C24 1.482(7) . ?
C8 C9 1.477(7) . ?
C8 H8 0.9300 . ?
C9 N1 1.469(6) . ?
C9 C17 1.517(7) . ?
C9 H9 0.9800 . ?
C10 N1 1.446(6) . ?
C10 C11 1.504(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.376(7) . ?
C11 C12 1.383(8) . ?
C12 C13 1.383(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.356(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.362(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.364(9) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.370(7) . ?
C17 C22 1.383(6) . ?
C18 C19 1.368(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.392(7) . ?
C19 H19 0.9300 . ?
C20 O3 1.365(6) . ?
C20 C21 1.372(8) . ?
C21 C22 1.383(7) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 O3 1.427(7) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 O1 1.190(6) . ?
C24 O2 1.328(6) . ?
C25 O2 1.429(7) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
N1 C1 C2 122.7(5) . . ?
N1 C1 C6 119.2(4) . . ?
C2 C1 C6 118.1(4) . . ?
C3 C2 C1 121.0(5) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C4 C3 C2 120.8(5) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.0(5) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.7(5) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 119.3(4) . . ?
C5 C6 C7 123.7(5) . . ?
C1 C6 C7 117.0(4) . . ?
C8 C7 C6 119.8(4) . . ?
C8 C7 C24 119.6(4) . . ?
C6 C7 C24 120.5(4) . . ?
C7 C8 C9 123.4(4) . . ?
C7 C8 H8 118.3 . . ?
C9 C8 H8 118.3 . . ?
N1 C9 C8 109.4(4) . . ?
N1 C9 C17 113.1(4) . . ?
C8 C9 C17 112.3(4) . . ?
N1 C9 H9 107.2 . . ?
C8 C9 H9 107.2 . . ?
C17 C9 H9 107.2 . . ?
N1 C10 C11 114.7(4) . . ?
N1 C10 H10A 108.6 . . ?
C11 C10 H10A 108.6 . . ?
N1 C10 H10B 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C16 C11 C12 118.3(5) . . ?
C16 C11 C10 119.8(5) . . ?
C12 C11 C10 121.8(5) . . ?
C11 C12 C13 120.1(6) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.5(6) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.6(6) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120.8(6) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C11 120.7(6) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C18 C17 C22 118.2(5) . . ?
C18 C17 C9 121.1(4) . . ?
C22 C17 C9 120.8(4) . . ?
C19 C18 C17 121.7(4) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 119.8(5) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
O3 C20 C21 125.2(5) . . ?
O3 C20 C19 115.3(5) . . ?
C21 C20 C19 119.5(5) . . ?
C20 C21 C22 119.7(5) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C21 C22 C17 121.2(5) . . ?
C21 C22 H22 119.4 . . ?
C17 C22 H22 119.4 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O1 C24 O2 122.6(5) . . ?
O1 C24 C7 125.1(5) . . ?
O2 C24 C7 112.2(4) . . ?
O2 C25 H25A 109.5 . . ?
O2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C1 N1 C10 119.3(4) . . ?
C1 N1 C9 120.8(4) . . ?
C10 N1 C9 114.4(4) . . ?
C24 O2 C25 116.5(4) . . ?
C20 O3 C23 117.6(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
N1 C1 C2 C3 179.9(5) . . . . ?
C6 C1 C2 C3 -2.5(8) . . . . ?
C1 C2 C3 C4 -0.9(9) . . . . ?
C2 C3 C4 C5 2.2(10) . . . . ?
C3 C4 C5 C6 -0.1(9) . . . . ?
C4 C5 C6 C1 -3.3(8) . . . . ?
C4 C5 C6 C7 178.2(5) . . . . ?
N1 C1 C6 C5 -177.8(4) . . . . ?
C2 C1 C6 C5 4.5(7) . . . . ?
N1 C1 C6 C7 0.8(7) . . . . ?
C2 C1 C6 C7 -176.9(4) . . . . ?
C5 C6 C7 C8 163.2(5) . . . . ?
C1 C6 C7 C8 -15.3(7) . . . . ?
C5 C6 C7 C24 -21.2(7) . . . . ?
C1 C6 C7 C24 160.2(4) . . . . ?
C6 C7 C8 C9 2.3(8) . . . . ?
C24 C7 C8 C9 -173.3(5) . . . . ?
C7 C8 C9 N1 22.3(7) . . . . ?
C7 C8 C9 C17 -104.1(5) . . . . ?
N1 C10 C11 C16 -158.5(5) . . . . ?
N1 C10 C11 C12 24.8(7) . . . . ?
C16 C11 C12 C13 -0.6(8) . . . . ?
C10 C11 C12 C13 176.1(5) . . . . ?
C11 C12 C13 C14 0.2(9) . . . . ?
C12 C13 C14 C15 0.0(9) . . . . ?
C13 C14 C15 C16 0.0(10) . . . . ?
C14 C15 C16 C11 -0.4(10) . . . . ?
C12 C11 C16 C15 0.7(8) . . . . ?
C10 C11 C16 C15 -176.1(5) . . . . ?
N1 C9 C17 C18 -63.7(6) . . . . ?
C8 C9 C17 C18 60.8(6) . . . . ?
N1 C9 C17 C22 116.0(5) . . . . ?
C8 C9 C17 C22 -119.5(5) . . . . ?
C22 C17 C18 C19 -0.9(7) . . . . ?
C9 C17 C18 C19 178.9(5) . . . . ?
C17 C18 C19 C20 0.6(8) . . . . ?
C18 C19 C20 O3 179.9(5) . . . . ?
C18 C19 C20 C21 0.3(8) . . . . ?
O3 C20 C21 C22 179.5(5) . . . . ?
C19 C20 C21 C22 -0.9(8) . . . . ?
C20 C21 C22 C17 0.6(8) . . . . ?
C18 C17 C22 C21 0.3(8) . . . . ?
C9 C17 C22 C21 -179.5(5) . . . . ?
C8 C7 C24 O1 157.8(6) . . . . ?
C6 C7 C24 O1 -17.8(8) . . . . ?
C8 C7 C24 O2 -19.2(7) . . . . ?
C6 C7 C24 O2 165.2(4) . . . . ?
C2 C1 N1 C10 -2.8(7) . . . . ?
C6 C1 N1 C10 179.6(4) . . . . ?
C2 C1 N1 C9 -155.4(5) . . . . ?
C6 C1 N1 C9 27.1(7) . . . . ?
C11 C10 N1 C1 79.2(6) . . . . ?
C11 C10 N1 C9 -126.5(5) . . . . ?
C8 C9 N1 C1 -37.3(6) . . . . ?
C17 C9 N1 C1 88.7(5) . . . . ?
C8 C9 N1 C10 168.9(4) . . . . ?
C17 C9 N1 C10 -65.1(6) . . . . ?
O1 C24 O2 C25 -4.8(8) . . . . ?
C7 C24 O2 C25 172.4(5) . . . . ?
C21 C20 O3 C23 0.3(9) . . . . ?
C19 C20 O3 C23 -179.3(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.081