# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_z
_database_code_depnum_ccdc_archive 'CCDC 975762'
_audit_update_record             
;
2013-12-07 deposited with the CCDC.
2015-04-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H23 N O4'
_chemical_formula_weight         389.43

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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9379(6)
_cell_length_b                   10.0008(6)
_cell_length_c                   10.8276(6)
_cell_angle_alpha                96.918(2)
_cell_angle_beta                 104.753(2)
_cell_angle_gamma                99.920(2)
_cell_volume                     1009.72(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9643
_exptl_absorpt_correction_T_max  0.9811
_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_reflns_number            11829
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3528
_reflns_number_gt                2240
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0507P)²+0.1786P] 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         3528
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.0989
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 -0.02977(14) 0.22674(15) 0.87052(17) 0.0572(5) Uani 1 1 d . . .
O2 O 0.14243(15) 0.41280(15) 0.90514(16) 0.0566(5) Uani 1 1 d . . .
O3 O 0.62687(15) 0.38055(16) 1.07838(16) 0.0609(5) Uani 1 1 d . . .
H3A H 0.6971 0.4413 1.0866 0.091 Uiso 1 1 calc R . .
O4 O 0.13492(14) 0.06078(13) 0.91782(14) 0.0445(4) Uani 1 1 d . . .
N1 N 0.42035(17) 0.15574(17) 1.07539(17) 0.0407(4) Uani 1 1 d . . .
C1 C 0.2651(2) 0.2959(2) 1.1570(2) 0.0415(5) Uani 1 1 d . . .
C2 C 0.1426(2) 0.2220(2) 1.1763(2) 0.0483(6) Uani 1 1 d . . .
H2A H 0.0912 0.1429 1.1176 0.058 Uiso 1 1 calc R . .
C3 C 0.0960(2) 0.2643(3) 1.2813(2) 0.0579(7) Uani 1 1 d . . .
H3B H 0.0126 0.2148 1.2917 0.069 Uiso 1 1 calc R . .
C4 C 0.1722(3) 0.3789(3) 1.3704(3) 0.0613(7) Uani 1 1 d . . .
H4A H 0.1408 0.4067 1.4414 0.074 Uiso 1 1 calc R . .
C5 C 0.2945(3) 0.4526(3) 1.3547(3) 0.0582(7) Uani 1 1 d . . .
H5A H 0.3469 0.5298 1.4155 0.070 Uiso 1 1 calc R . .
C6 C 0.3402(2) 0.4122(2) 1.2485(2) 0.0511(6) Uani 1 1 d . . .
H6A H 0.4226 0.4636 1.2379 0.061 Uiso 1 1 calc R . .
C7 C 0.2629(2) 0.1903(2) 0.7939(2) 0.0446(6) Uani 1 1 d . . .
C8 C 0.4004(2) 0.2443(2) 0.7934(2) 0.0487(6) Uani 1 1 d . . .
H8A H 0.4687 0.2865 0.8706 0.058 Uiso 1 1 calc R . .
C9 C 0.4364(3) 0.2356(2) 0.6777(3) 0.0587(7) Uani 1 1 d . . .
H9A H 0.5293 0.2716 0.6781 0.070 Uiso 1 1 calc R . .
C10 C 0.3377(3) 0.1748(3) 0.5626(3) 0.0647(7) Uani 1 1 d . . .
H10A H 0.3626 0.1708 0.4853 0.078 Uiso 1 1 calc R . .
C11 C 0.2016(3) 0.1199(3) 0.5631(3) 0.0745(8) Uani 1 1 d . . .
H11A H 0.1339 0.0773 0.4856 0.089 Uiso 1 1 calc R . .
C12 C 0.1646(3) 0.1274(3) 0.6766(3) 0.0629(7) Uani 1 1 d . . .
H12A H 0.0718 0.0897 0.6752 0.075 Uiso 1 1 calc R . .
C13 C 0.5394(2) 0.2077(2) 1.1865(2) 0.0417(5) Uani 1 1 d . . .
C14 C 0.5603(2) 0.1457(2) 1.2965(2) 0.0534(6) Uani 1 1 d . . .
H14A H 0.4923 0.0706 1.2996 0.064 Uiso 1 1 calc R . .
C15 C 0.6801(3) 0.1935(3) 1.4013(3) 0.0637(7) Uani 1 1 d . . .
H15A H 0.6923 0.1497 1.4732 0.076 Uiso 1 1 calc R . .
C16 C 0.7806(3) 0.3048(3) 1.3996(3) 0.0619(7) Uani 1 1 d . . .
H16A H 0.8609 0.3369 1.4701 0.074 Uiso 1 1 calc R . .
C17 C 0.7621(2) 0.3691(3) 1.2926(3) 0.0563(7) Uani 1 1 d . . .
H17A H 0.8295 0.4457 1.2916 0.068 Uiso 1 1 calc R . .
C18 C 0.6446(2) 0.3208(2) 1.1875(2) 0.0453(6) Uani 1 1 d . . .
C19 C 0.2102(2) 0.1946(2) 0.9154(2) 0.0410(5) Uani 1 1 d . . .
C20 C 0.3252(2) 0.2545(2) 1.0458(2) 0.0397(5) Uani 1 1 d . . .
H20A H 0.3835 0.3384 1.0330 0.048 Uiso 1 1 calc R . .
C21 C 0.3400(2) 0.0171(2) 1.0712(2) 0.0469(6) Uani 1 1 d . . .
H21A H 0.2933 0.0183 1.1397 0.056 Uiso 1 1 calc R . .
H21B H 0.4045 -0.0458 1.0849 0.056 Uiso 1 1 calc R . .
C22 C 0.2314(2) -0.0309(2) 0.9426(2) 0.0486(6) Uani 1 1 d . . .
H22A H 0.2791 -0.0366 0.8749 0.058 Uiso 1 1 calc R . .
H22B H 0.1781 -0.1224 0.9405 0.058 Uiso 1 1 calc R . .
C23 C 0.1045(2) 0.2897(2) 0.8977(2) 0.0442(6) Uani 1 1 d . . .
C24 C -0.1324(2) 0.3148(3) 0.8498(3) 0.0890(10) Uani 1 1 d . . .
H24A H -0.2268 0.2598 0.8310 0.133 Uiso 1 1 calc R . .
H24B H -0.1245 0.3606 0.7782 0.133 Uiso 1 1 calc R . .
H24C H -0.1138 0.3821 0.9265 0.133 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 C23 1.315(2) . ?
O1 C24 1.451(3) . ?
O2 C23 1.211(2) . ?
O3 C18 1.373(3) . ?
O3 H3A 0.8200 . ?
O4 C19 1.423(2) . ?
O4 C22 1.437(2) . ?
N1 C13 1.425(3) . ?
N1 C21 1.465(2) . ?
N1 C20 1.489(2) . ?
C1 C2 1.389(3) . ?
C1 C6 1.392(3) . ?
C1 C20 1.519(3) . ?
C2 C3 1.380(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3B 0.9300 . ?
C4 C5 1.370(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.381(3) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.382(3) . ?
C7 C12 1.388(3) . ?
C7 C19 1.534(3) . ?
C8 C9 1.385(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.368(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.371(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.367(4) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C14 1.393(3) . ?
C13 C18 1.399(3) . ?
C14 C15 1.386(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.366(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.379(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.374(3) . ?
C17 H17A 0.9300 . ?
C19 C23 1.527(3) . ?
C19 C20 1.549(3) . ?
C20 H20A 0.9800 . ?
C21 C22 1.493(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C23 O1 C24 115.66(18) . . ?
C18 O3 H3A 109.5 . . ?
C19 O4 C22 110.32(14) . . ?
C13 N1 C21 115.63(17) . . ?
C13 N1 C20 113.46(16) . . ?
C21 N1 C20 111.94(15) . . ?
C2 C1 C6 117.6(2) . . ?
C2 C1 C20 124.18(19) . . ?
C6 C1 C20 118.15(18) . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2A 119.5 . . ?
C1 C2 H2A 119.5 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3B 119.8 . . ?
C2 C3 H3B 119.8 . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C5 C6 C1 121.2(2) . . ?
C5 C6 H6A 119.4 . . ?
C1 C6 H6A 119.4 . . ?
C8 C7 C12 118.2(2) . . ?
C8 C7 C19 124.7(2) . . ?
C12 C7 C19 117.15(19) . . ?
C7 C8 C9 119.9(2) . . ?
C7 C8 H8A 120.1 . . ?
C9 C8 H8A 120.1 . . ?
C10 C9 C8 121.2(2) . . ?
C10 C9 H9A 119.4 . . ?
C8 C9 H9A 119.4 . . ?
C9 C10 C11 119.0(3) . . ?
C9 C10 H10A 120.5 . . ?
C11 C10 H10A 120.5 . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11A 119.8 . . ?
C10 C11 H11A 119.8 . . ?
C11 C12 C7 121.3(2) . . ?
C11 C12 H12A 119.4 . . ?
C7 C12 H12A 119.4 . . ?
C14 C13 C18 116.8(2) . . ?
C14 C13 N1 122.2(2) . . ?
C18 C13 N1 120.9(2) . . ?
C15 C14 C13 121.5(2) . . ?
C15 C14 H14A 119.3 . . ?
C13 C14 H14A 119.3 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C15 C16 C17 119.6(2) . . ?
C15 C16 H16A 120.2 . . ?
C17 C16 H16A 120.2 . . ?
C18 C17 C16 120.4(2) . . ?
C18 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
O3 C18 C17 121.2(2) . . ?
O3 C18 C13 117.32(19) . . ?
C17 C18 C13 121.5(2) . . ?
O4 C19 C23 108.08(15) . . ?
O4 C19 C7 109.27(17) . . ?
C23 C19 C7 105.09(17) . . ?
O4 C19 C20 111.07(17) . . ?
C23 C19 C20 107.06(17) . . ?
C7 C19 C20 115.82(16) . . ?
N1 C20 C1 112.63(17) . . ?
N1 C20 C19 108.94(16) . . ?
C1 C20 C19 113.91(16) . . ?
N1 C20 H20A 107.0 . . ?
C1 C20 H20A 107.0 . . ?
C19 C20 H20A 107.0 . . ?
N1 C21 C22 109.67(18) . . ?
N1 C21 H21A 109.7 . . ?
C22 C21 H21A 109.7 . . ?
N1 C21 H21B 109.7 . . ?
C22 C21 H21B 109.7 . . ?
H21A C21 H21B 108.2 . . ?
O4 C22 C21 111.43(17) . . ?
O4 C22 H22A 109.3 . . ?
C21 C22 H22A 109.3 . . ?
O4 C22 H22B 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
O2 C23 O1 123.2(2) . . ?
O2 C23 C19 122.01(18) . . ?
O1 C23 C19 114.74(18) . . ?
O1 C24 H24A 109.5 . . ?
O1 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O1 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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 1.2(3) . . . . ?
C20 C1 C2 C3 178.6(2) . . . . ?
C1 C2 C3 C4 -1.5(4) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 C1 -1.0(4) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C20 C1 C6 C5 -177.5(2) . . . . ?
C12 C7 C8 C9 0.4(3) . . . . ?
C19 C7 C8 C9 -179.6(2) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
C8 C9 C10 C11 -1.0(4) . . . . ?
C9 C10 C11 C12 0.8(4) . . . . ?
C10 C11 C12 C7 0.0(4) . . . . ?
C8 C7 C12 C11 -0.6(4) . . . . ?
C19 C7 C12 C11 179.4(2) . . . . ?
C21 N1 C13 C14 -13.6(3) . . . . ?
C20 N1 C13 C14 117.7(2) . . . . ?
C21 N1 C13 C18 163.55(18) . . . . ?
C20 N1 C13 C18 -65.2(2) . . . . ?
C18 C13 C14 C15 -0.4(3) . . . . ?
N1 C13 C14 C15 176.9(2) . . . . ?
C13 C14 C15 C16 0.8(4) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
C15 C16 C17 C18 -0.9(4) . . . . ?
C16 C17 C18 O3 -177.7(2) . . . . ?
C16 C17 C18 C13 1.4(3) . . . . ?
C14 C13 C18 O3 178.4(2) . . . . ?
N1 C13 C18 O3 1.1(3) . . . . ?
C14 C13 C18 C17 -0.7(3) . . . . ?
N1 C13 C18 C17 -178.0(2) . . . . ?
C22 O4 C19 C23 -176.34(17) . . . . ?
C22 O4 C19 C7 69.8(2) . . . . ?
C22 O4 C19 C20 -59.2(2) . . . . ?
C8 C7 C19 O4 -131.2(2) . . . . ?
C12 C7 C19 O4 48.9(3) . . . . ?
C8 C7 C19 C23 113.1(2) . . . . ?
C12 C7 C19 C23 -66.9(2) . . . . ?
C8 C7 C19 C20 -4.8(3) . . . . ?
C12 C7 C19 C20 175.2(2) . . . . ?
C13 N1 C20 C1 -59.0(2) . . . . ?
C21 N1 C20 C1 74.1(2) . . . . ?
C13 N1 C20 C19 173.57(16) . . . . ?
C21 N1 C20 C19 -53.3(2) . . . . ?
C2 C1 C20 N1 -86.1(2) . . . . ?
C6 C1 C20 N1 91.3(2) . . . . ?
C2 C1 C20 C19 38.6(3) . . . . ?
C6 C1 C20 C19 -143.94(19) . . . . ?
O4 C19 C20 N1 55.1(2) . . . . ?
C23 C19 C20 N1 172.86(15) . . . . ?
C7 C19 C20 N1 -70.3(2) . . . . ?
O4 C19 C20 C1 -71.6(2) . . . . ?
C23 C19 C20 C1 46.2(2) . . . . ?
C7 C19 C20 C1 163.00(17) . . . . ?
C13 N1 C21 C22 -172.53(17) . . . . ?
C20 N1 C21 C22 55.5(2) . . . . ?
C19 O4 C22 C21 61.3(2) . . . . ?
N1 C21 C22 O4 -58.6(2) . . . . ?
C24 O1 C23 O2 -0.2(3) . . . . ?
C24 O1 C23 C19 -178.4(2) . . . . ?
O4 C19 C23 O2 172.5(2) . . . . ?
C7 C19 C23 O2 -70.9(3) . . . . ?
C20 C19 C23 O2 52.8(3) . . . . ?
O4 C19 C23 O1 -9.3(3) . . . . ?
C7 C19 C23 O1 107.3(2) . . . . ?
C20 C19 C23 O1 -129.00(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.036
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_z
_database_code_depnum_ccdc_archive 'CCDC 975763'
_audit_update_record             
;
2013-12-07 deposited with the CCDC.
2015-04-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22 Br N O5'
_chemical_formula_weight         496.35

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'
Br Br -0.2901 2.4595 '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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6542(8)
_cell_length_b                   10.7705(9)
_cell_length_c                   12.1323(9)
_cell_angle_alpha                87.694(2)
_cell_angle_beta                 71.902(2)
_cell_angle_gamma                69.127(2)
_cell_volume                     1116.89(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_absorpt_coefficient_mu    1.877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5061
_exptl_absorpt_correction_T_max  0.7287
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13055
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3902
_reflns_number_gt                3380
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0409P)²+0.6809P] 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         3902
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0770
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
Br1 Br 0.25892(4) 0.31205(3) -0.17161(2) 0.05130(12) Uani 1 1 d . . .
O1 O 0.1369(2) 0.57804(19) 0.54324(16) 0.0500(5) Uani 1 1 d . . .
O2 O 0.1358(2) 0.77439(18) 0.47749(16) 0.0441(4) Uani 1 1 d . . .
O3 O 0.27332(19) 0.67081(17) 0.25363(14) 0.0362(4) Uani 1 1 d . . .
O4 O 0.2151(3) 0.3045(2) 0.58942(16) 0.0620(6) Uani 1 1 d . . .
H4A H 0.2007 0.3762 0.5604 0.093 Uiso 1 1 calc R . .
O5 O 0.5859(2) 0.3115(2) 0.40200(18) 0.0506(5) Uani 1 1 d . . .
N1 N 0.3589(2) 0.3500(2) 0.36118(17) 0.0320(4) Uani 1 1 d . . .
C1 C 0.2803(3) 0.2039(3) 0.5036(2) 0.0428(6) Uani 1 1 d . . .
C2 C 0.2802(4) 0.0786(3) 0.5338(3) 0.0548(8) Uani 1 1 d . . .
H2A H 0.2386 0.0643 0.6112 0.066 Uiso 1 1 calc R . .
C3 C 0.3414(4) -0.0242(3) 0.4495(4) 0.0621(9) Uani 1 1 d . . .
H3A H 0.3428 -0.1085 0.4703 0.074 Uiso 1 1 calc R . .
C4 C 0.4012(4) -0.0045(3) 0.3342(4) 0.0646(9) Uani 1 1 d . . .
H4B H 0.4386 -0.0742 0.2773 0.077 Uiso 1 1 calc R . .
C5 C 0.4053(3) 0.1191(3) 0.3035(3) 0.0492(7) Uani 1 1 d . . .
H5A H 0.4468 0.1327 0.2259 0.059 Uiso 1 1 calc R . .
C6 C 0.3480(3) 0.2224(2) 0.3879(2) 0.0356(6) Uani 1 1 d . . .
C7 C 0.2511(3) 0.4207(2) 0.1988(2) 0.0316(5) Uani 1 1 d . . .
C8 C 0.3863(3) 0.3934(3) 0.1049(2) 0.0397(6) Uani 1 1 d . . .
H8A H 0.4755 0.3978 0.1162 0.048 Uiso 1 1 calc R . .
C9 C 0.3909(3) 0.3598(3) -0.0049(2) 0.0409(6) Uani 1 1 d . . .
H9A H 0.4822 0.3420 -0.0674 0.049 Uiso 1 1 calc R . .
C10 C 0.2588(3) 0.3527(3) -0.0211(2) 0.0368(6) Uani 1 1 d . . .
C11 C 0.1232(3) 0.3774(3) 0.0713(2) 0.0434(6) Uani 1 1 d . . .
H11A H 0.0346 0.3718 0.0598 0.052 Uiso 1 1 calc R . .
C12 C 0.1201(3) 0.4105(3) 0.1813(2) 0.0390(6) Uani 1 1 d . . .
H12A H 0.0295 0.4261 0.2441 0.047 Uiso 1 1 calc R . .
C13 C 0.1639(4) 0.7412(4) 0.0249(3) 0.0665(9) Uani 1 1 d . . .
H13A H 0.1471 0.6611 0.0302 0.080 Uiso 1 1 calc R . .
C14 C 0.1952(5) 0.7929(7) -0.0811(4) 0.1056(19) Uani 1 1 d . . .
H14A H 0.1985 0.7484 -0.1466 0.127 Uiso 1 1 calc R . .
C15 C 0.2207(5) 0.9065(8) -0.0900(6) 0.123(3) Uani 1 1 d . . .
H15A H 0.2413 0.9411 -0.1622 0.147 Uiso 1 1 calc R . .
C16 C 0.2175(6) 0.9751(5) 0.0056(7) 0.117(2) Uani 1 1 d . . .
H16A H 0.2370 1.0541 -0.0022 0.141 Uiso 1 1 calc R . .
C17 C 0.1838(4) 0.9218(4) 0.1162(4) 0.0786(11) Uani 1 1 d . . .
H17A H 0.1804 0.9659 0.1819 0.094 Uiso 1 1 calc R . .
C18 C 0.1566(3) 0.8050(3) 0.1244(2) 0.0434(6) Uani 1 1 d . . .
C19 C 0.1245(3) 0.7435(3) 0.2376(2) 0.0435(6) Uani 1 1 d . . .
H19A H 0.0600 0.8120 0.3008 0.052 Uiso 1 1 calc R . .
H19B H 0.0698 0.6837 0.2361 0.052 Uiso 1 1 calc R . .
C20 C 0.2775(3) 0.5822(2) 0.3417(2) 0.0323(5) Uani 1 1 d . . .
C21 C 0.4463(3) 0.5266(3) 0.3440(2) 0.0369(6) Uani 1 1 d . . .
H21A H 0.5181 0.5309 0.2689 0.044 Uiso 1 1 calc R . .
H21B H 0.4586 0.5768 0.4025 0.044 Uiso 1 1 calc R . .
C22 C 0.4765(3) 0.3843(3) 0.3729(2) 0.0348(6) Uani 1 1 d . . .
C23 C 0.2418(3) 0.4543(2) 0.3214(2) 0.0306(5) Uani 1 1 d . . .
H23A H 0.1375 0.4644 0.3738 0.037 Uiso 1 1 calc R . .
C24 C 0.1737(3) 0.6445(3) 0.4650(2) 0.0364(6) Uani 1 1 d . . .
C25 C 0.0492(4) 0.8361(3) 0.5947(2) 0.0514(7) Uani 1 1 d . . .
H25A H 0.0271 0.9304 0.5947 0.077 Uiso 1 1 calc R . .
H25B H 0.1103 0.7987 0.6452 0.077 Uiso 1 1 calc R . .
H25C H -0.0472 0.8202 0.6217 0.077 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
Br1 C10 1.895(2) . ?
O1 C24 1.207(3) . ?
O2 C24 1.316(3) . ?
O2 C25 1.450(3) . ?
O3 C20 1.404(3) . ?
O3 C19 1.441(3) . ?
O4 C1 1.361(3) . ?
O4 H4A 0.8200 . ?
O5 C22 1.214(3) . ?
N1 C22 1.360(3) . ?
N1 C6 1.432(3) . ?
N1 C23 1.471(3) . ?
C1 C2 1.385(4) . ?
C1 C6 1.391(4) . ?
C2 C3 1.367(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.378(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.378(4) . ?
C4 H4B 0.9300 . ?
C5 C6 1.376(4) . ?
C5 H5A 0.9300 . ?
C7 C8 1.385(3) . ?
C7 C12 1.387(3) . ?
C7 C23 1.513(3) . ?
C8 C9 1.378(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.377(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.381(4) . ?
C11 C12 1.384(4) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C14 1.370(6) . ?
C13 C18 1.383(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.326(9) . ?
C14 H14A 0.9300 . ?
C15 C16 1.387(9) . ?
C15 H15A 0.9300 . ?
C16 C17 1.427(7) . ?
C16 H16A 0.9300 . ?
C17 C18 1.368(5) . ?
C17 H17A 0.9300 . ?
C18 C19 1.493(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.532(3) . ?
C20 C24 1.537(3) . ?
C20 C23 1.579(3) . ?
C21 C22 1.503(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C23 H23A 0.9800 . ?
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
C24 O2 C25 115.8(2) . . ?
C20 O3 C19 118.03(18) . . ?
C1 O4 H4A 109.5 . . ?
C22 N1 C6 122.4(2) . . ?
C22 N1 C23 115.21(19) . . ?
C6 N1 C23 122.36(18) . . ?
O4 C1 C2 118.2(3) . . ?
O4 C1 C6 122.5(2) . . ?
C2 C1 C6 119.3(3) . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4B 120.2 . . ?
C3 C4 H4B 120.2 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 N1 121.8(2) . . ?
C1 C6 N1 117.9(2) . . ?
C8 C7 C12 118.9(2) . . ?
C8 C7 C23 122.9(2) . . ?
C12 C7 C23 118.1(2) . . ?
C9 C8 C7 121.1(2) . . ?
C9 C8 H8A 119.5 . . ?
C7 C8 H8A 119.5 . . ?
C10 C9 C8 119.2(2) . . ?
C10 C9 H9A 120.4 . . ?
C8 C9 H9A 120.4 . . ?
C9 C10 C11 120.8(2) . . ?
C9 C10 Br1 120.42(19) . . ?
C11 C10 Br1 118.72(19) . . ?
C10 C11 C12 119.4(2) . . ?
C10 C11 H11A 120.3 . . ?
C12 C11 H11A 120.3 . . ?
C11 C12 C7 120.5(2) . . ?
C11 C12 H12A 119.7 . . ?
C7 C12 H12A 119.7 . . ?
C14 C13 C18 121.9(4) . . ?
C14 C13 H13A 119.1 . . ?
C18 C13 H13A 119.1 . . ?
C15 C14 C13 119.7(5) . . ?
C15 C14 H14A 120.2 . . ?
C13 C14 H14A 120.2 . . ?
C14 C15 C16 121.8(5) . . ?
C14 C15 H15A 119.1 . . ?
C16 C15 H15A 119.1 . . ?
C15 C16 C17 118.5(5) . . ?
C15 C16 H16A 120.7 . . ?
C17 C16 H16A 120.7 . . ?
C18 C17 C16 119.2(5) . . ?
C18 C17 H17A 120.4 . . ?
C16 C17 H17A 120.4 . . ?
C17 C18 C13 119.0(3) . . ?
C17 C18 C19 121.3(3) . . ?
C13 C18 C19 119.7(3) . . ?
O3 C19 C18 107.1(2) . . ?
O3 C19 H19A 110.3 . . ?
C18 C19 H19A 110.3 . . ?
O3 C19 H19B 110.3 . . ?
C18 C19 H19B 110.3 . . ?
H19A C19 H19B 108.5 . . ?
O3 C20 C21 106.71(18) . . ?
O3 C20 C24 115.4(2) . . ?
C21 C20 C24 106.68(19) . . ?
O3 C20 C23 115.93(19) . . ?
C21 C20 C23 104.17(19) . . ?
C24 C20 C23 107.03(18) . . ?
C22 C21 C20 105.66(19) . . ?
C22 C21 H21A 110.6 . . ?
C20 C21 H21A 110.6 . . ?
C22 C21 H21B 110.6 . . ?
C20 C21 H21B 110.6 . . ?
H21A C21 H21B 108.7 . . ?
O5 C22 N1 125.3(2) . . ?
O5 C22 C21 126.7(2) . . ?
N1 C22 C21 108.0(2) . . ?
N1 C23 C7 112.18(19) . . ?
N1 C23 C20 101.68(17) . . ?
C7 C23 C20 116.65(19) . . ?
N1 C23 H23A 108.7 . . ?
C7 C23 H23A 108.7 . . ?
C20 C23 H23A 108.7 . . ?
O1 C24 O2 123.9(2) . . ?
O1 C24 C20 122.2(2) . . ?
O2 C24 C20 113.8(2) . . ?
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 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.054
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_z
_database_code_depnum_ccdc_archive 'CCDC 975764'
_audit_update_record             
;
2013-12-07 deposited with the CCDC.
2015-04-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H25 N O7'
_chemical_formula_weight         487.49

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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1316(14)
_cell_length_b                   11.5658(17)
_cell_length_c                   12.884(2)
_cell_angle_alpha                87.471(5)
_cell_angle_beta                 84.937(5)
_cell_angle_gamma                78.960(5)
_cell_volume                     1329.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9607
_exptl_absorpt_correction_T_max  0.9904
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15678
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4654
_reflns_number_gt                3204
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0735P)²+0.2990P] 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         4654
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1464
_refine_ls_wR_factor_gt          0.1250
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
O01 O 0.8961(3) 0.7644(2) 0.62838(19) 0.1095(8) Uani 1 1 d . . .
O1 O 0.24271(18) 1.10036(13) 0.16644(12) 0.0604(4) Uani 1 1 d . . .
O2 O 0.32181(19) 0.93296(14) 0.08443(12) 0.0638(5) Uani 1 1 d . . .
O3 O 0.53943(18) 0.68881(14) 0.08595(13) 0.0646(5) Uani 1 1 d . . .
H3A H 0.4739 0.7479 0.0932 0.097 Uiso 1 1 calc R . .
O4 O 0.78308(18) 0.71993(17) 0.45954(13) 0.0766(6) Uani 1 1 d . . .
H4B H 0.8126 0.7322 0.5156 0.115 Uiso 1 1 calc R . .
O5 O 0.57128(18) 0.82504(16) 0.52785(13) 0.0688(5) Uani 1 1 d . . .
O6 O 0.22309(15) 0.97252(11) 0.34239(10) 0.0449(4) Uani 1 1 d . . .
N1 N 0.36038(17) 0.75289(13) 0.25788(12) 0.0396(4) Uani 1 1 d . . .
C1 C 0.0026(2) 0.98420(16) 0.25514(15) 0.0407(5) Uani 1 1 d . . .
C2 C -0.0810(2) 0.9958(2) 0.35045(18) 0.0549(6) Uani 1 1 d . . .
H2A H -0.0347 0.9726 0.4114 0.066 Uiso 1 1 calc R . .
C3 C -0.2324(3) 1.0415(2) 0.3556(2) 0.0651(7) Uani 1 1 d . . .
H3B H -0.2872 1.0492 0.4201 0.078 Uiso 1 1 calc R . .
C4 C -0.3028(3) 1.0756(2) 0.2671(2) 0.0613(6) Uani 1 1 d . . .
H4A H -0.4044 1.1080 0.2712 0.074 Uiso 1 1 calc R . .
C5 C -0.2224(3) 1.0616(2) 0.1720(2) 0.0638(6) Uani 1 1 d . . .
H5A H -0.2703 1.0821 0.1112 0.077 Uiso 1 1 calc R . .
C6 C -0.0707(2) 1.0172(2) 0.16637(18) 0.0551(6) Uani 1 1 d . . .
H6A H -0.0169 1.0094 0.1015 0.066 Uiso 1 1 calc R . .
C7 C 0.1193(2) 0.73952(17) 0.18037(16) 0.0433(5) Uani 1 1 d . . .
C8 C -0.0060(3) 0.6954(2) 0.2177(2) 0.0617(6) Uani 1 1 d . . .
H8A H -0.0364 0.6990 0.2885 0.074 Uiso 1 1 calc R . .
C9 C -0.0867(3) 0.6462(2) 0.1521(3) 0.0784(8) Uani 1 1 d . . .
H9A H -0.1707 0.6171 0.1792 0.094 Uiso 1 1 calc R . .
C10 C -0.0452(3) 0.6396(2) 0.0481(3) 0.0736(8) Uani 1 1 d . . .
H10A H -0.1008 0.6071 0.0040 0.088 Uiso 1 1 calc R . .
C11 C 0.0787(3) 0.6813(2) 0.0098(2) 0.0699(7) Uani 1 1 d . . .
H11A H 0.1082 0.6768 -0.0611 0.084 Uiso 1 1 calc R . .
C12 C 0.1620(3) 0.7306(2) 0.07506(18) 0.0558(6) Uani 1 1 d . . .
H12A H 0.2472 0.7577 0.0476 0.067 Uiso 1 1 calc R . .
C13 C 0.4083(2) 0.62888(17) 0.23964(16) 0.0430(5) Uani 1 1 d . . .
C14 C 0.3718(3) 0.5392(2) 0.3046(2) 0.0656(7) Uani 1 1 d . . .
H14A H 0.3076 0.5563 0.3643 0.079 Uiso 1 1 calc R . .
C15 C 0.4318(4) 0.4218(2) 0.2800(3) 0.0860(9) Uani 1 1 d . . .
H15A H 0.4083 0.3605 0.3236 0.103 Uiso 1 1 calc R . .
C16 C 0.5257(4) 0.3981(2) 0.1911(3) 0.0850(9) Uani 1 1 d . . .
H16A H 0.5656 0.3202 0.1751 0.102 Uiso 1 1 calc R . .
C17 C 0.5617(3) 0.4859(2) 0.1259(2) 0.0706(7) Uani 1 1 d . . .
H17A H 0.6249 0.4683 0.0658 0.085 Uiso 1 1 calc R . .
C18 C 0.5034(2) 0.60165(18) 0.15021(17) 0.0481(5) Uani 1 1 d . . .
C19 C 0.1688(2) 0.93392(17) 0.25096(14) 0.0396(5) Uani 1 1 d . . .
C20 C 0.1971(2) 0.79693(16) 0.25739(15) 0.0392(5) Uani 1 1 d . . .
H20A H 0.1540 0.7763 0.3265 0.047 Uiso 1 1 calc R . .
C21 C 0.4153(2) 0.79408(17) 0.35185(15) 0.0434(5) Uani 1 1 d . . .
H21A H 0.3633 0.7645 0.4143 0.052 Uiso 1 1 calc R . .
C22 C 0.3795(2) 0.92687(18) 0.34876(17) 0.0463(5) Uani 1 1 d . . .
H22A H 0.4115 0.9556 0.4110 0.056 Uiso 1 1 calc R . .
H22B H 0.4355 0.9560 0.2890 0.056 Uiso 1 1 calc R . .
C23 C 0.5827(2) 0.7510(2) 0.35496(17) 0.0516(5) Uani 1 1 d . . .
H23A H 0.6059 0.6675 0.3411 0.062 Uiso 1 1 calc R . .
H23B H 0.6343 0.7913 0.2997 0.062 Uiso 1 1 calc R . .
C24 C 0.6419(2) 0.77024(19) 0.45701(18) 0.0500(5) Uani 1 1 d . . .
C25 C 0.2525(2) 0.98570(18) 0.15619(16) 0.0437(5) Uani 1 1 d . . .
C26 C 0.3214(3) 1.1602(2) 0.0849(2) 0.0743(8) Uani 1 1 d . . .
H26A H 0.3069 1.2424 0.0996 0.111 Uiso 1 1 calc R . .
H26B H 0.2832 1.1511 0.0193 0.111 Uiso 1 1 calc R . .
H26C H 0.4263 1.1267 0.0817 0.111 Uiso 1 1 calc R . .
C01 C 1.1078(7) 0.6125(5) 0.6161(5) 0.184(2) Uani 1 1 d . . .
C02 C 1.0070(5) 0.6941(4) 0.6848(3) 0.1225(14) Uani 1 1 d . . .


_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
O01 C02 1.406(4) . ?
O1 C25 1.323(2) . ?
O1 C26 1.446(3) . ?
O2 C25 1.194(2) . ?
O3 C18 1.347(3) . ?
O3 H3A 0.8200 . ?
O4 C24 1.311(2) . ?
O4 H4B 0.8200 . ?
O5 C24 1.201(2) . ?
O6 C22 1.433(2) . ?
O6 C19 1.438(2) . ?
N1 C13 1.441(2) . ?
N1 C20 1.481(2) . ?
N1 C21 1.481(2) . ?
C1 C6 1.379(3) . ?
C1 C2 1.385(3) . ?
C1 C19 1.515(3) . ?
C2 C3 1.380(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.365(4) . ?
C3 H3B 0.9300 . ?
C4 C5 1.371(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.379(3) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.381(3) . ?
C7 C12 1.381(3) . ?
C7 C20 1.514(3) . ?
C8 C9 1.376(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.362(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.359(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.390(3) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C14 1.376(3) . ?
C13 C18 1.390(3) . ?
C14 C15 1.402(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.374(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.360(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.381(3) . ?
C17 H17A 0.9300 . ?
C19 C25 1.543(3) . ?
C19 C20 1.555(3) . ?
C20 H20A 0.9800 . ?
C21 C22 1.507(3) . ?
C21 C23 1.518(3) . ?
C21 H21A 0.9800 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.506(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C01 C02 1.455(6) . ?

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
C25 O1 C26 116.16(18) . . ?
C18 O3 H3A 109.5 . . ?
C24 O4 H4B 109.5 . . ?
C22 O6 C19 111.86(14) . . ?
C13 N1 C20 115.06(15) . . ?
C13 N1 C21 114.68(15) . . ?
C20 N1 C21 109.52(14) . . ?
C6 C1 C2 117.99(19) . . ?
C6 C1 C19 122.20(17) . . ?
C2 C1 C19 119.79(18) . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3B 119.6 . . ?
C2 C3 H3B 119.6 . . ?
C3 C4 C5 119.5(2) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C5 C6 C1 121.2(2) . . ?
C5 C6 H6A 119.4 . . ?
C1 C6 H6A 119.4 . . ?
C8 C7 C12 117.5(2) . . ?
C8 C7 C20 117.55(19) . . ?
C12 C7 C20 124.95(19) . . ?
C9 C8 C7 121.2(2) . . ?
C9 C8 H8A 119.4 . . ?
C7 C8 H8A 119.4 . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9A 119.6 . . ?
C8 C9 H9A 119.6 . . ?
C11 C10 C9 118.9(2) . . ?
C11 C10 H10A 120.5 . . ?
C9 C10 H10A 120.5 . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 H11A 119.5 . . ?
C12 C11 H11A 119.5 . . ?
C7 C12 C11 120.6(2) . . ?
C7 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C14 C13 C18 119.4(2) . . ?
C14 C13 N1 125.3(2) . . ?
C18 C13 N1 115.17(18) . . ?
C13 C14 C15 119.6(3) . . ?
C13 C14 H14A 120.2 . . ?
C15 C14 H14A 120.2 . . ?
C16 C15 C14 119.4(3) . . ?
C16 C15 H15A 120.3 . . ?
C14 C15 H15A 120.3 . . ?
C17 C16 C15 121.6(3) . . ?
C17 C16 H16A 119.2 . . ?
C15 C16 H16A 119.2 . . ?
C16 C17 C18 119.2(3) . . ?
C16 C17 H17A 120.4 . . ?
C18 C17 H17A 120.4 . . ?
O3 C18 C17 119.3(2) . . ?
O3 C18 C13 119.90(18) . . ?
C17 C18 C13 120.8(2) . . ?
O6 C19 C1 106.75(14) . . ?
O6 C19 C25 106.69(15) . . ?
C1 C19 C25 110.78(16) . . ?
O6 C19 C20 107.18(15) . . ?
C1 C19 C20 110.65(15) . . ?
C25 C19 C20 114.36(15) . . ?
N1 C20 C7 115.24(15) . . ?
N1 C20 C19 108.30(15) . . ?
C7 C20 C19 115.34(16) . . ?
N1 C20 H20A 105.7 . . ?
C7 C20 H20A 105.7 . . ?
C19 C20 H20A 105.7 . . ?
N1 C21 C22 107.77(16) . . ?
N1 C21 C23 111.10(16) . . ?
C22 C21 C23 110.16(17) . . ?
N1 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
C23 C21 H21A 109.3 . . ?
O6 C22 C21 112.56(16) . . ?
O6 C22 H22A 109.1 . . ?
C21 C22 H22A 109.1 . . ?
O6 C22 H22B 109.1 . . ?
C21 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C24 C23 C21 114.08(17) . . ?
C24 C23 H23A 108.7 . . ?
C21 C23 H23A 108.7 . . ?
C24 C23 H23B 108.7 . . ?
C21 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
O5 C24 O4 123.2(2) . . ?
O5 C24 C23 125.31(19) . . ?
O4 C24 C23 111.46(19) . . ?
O2 C25 O1 122.95(19) . . ?
O2 C25 C19 126.98(19) . . ?
O1 C25 C19 110.01(17) . . ?
O1 C26 H26A 109.5 . . ?
O1 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O1 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O01 C02 C01 110.3(4) . . ?

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 -1.4(3) . . . . ?
C19 C1 C2 C3 179.9(2) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 1.5(4) . . . . ?
C3 C4 C5 C6 -2.2(4) . . . . ?
C4 C5 C6 C1 1.2(4) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C19 C1 C6 C5 179.3(2) . . . . ?
C12 C7 C8 C9 -1.1(3) . . . . ?
C20 C7 C8 C9 177.3(2) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C8 C7 C12 C11 1.5(3) . . . . ?
C20 C7 C12 C11 -176.8(2) . . . . ?
C10 C11 C12 C7 -0.8(4) . . . . ?
C20 N1 C13 C14 -65.0(3) . . . . ?
C21 N1 C13 C14 63.4(3) . . . . ?
C20 N1 C13 C18 117.42(19) . . . . ?
C21 N1 C13 C18 -114.21(19) . . . . ?
C18 C13 C14 C15 0.5(4) . . . . ?
N1 C13 C14 C15 -177.0(2) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C14 C15 C16 C17 -0.2(5) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 O3 179.7(2) . . . . ?
C16 C17 C18 C13 -0.4(4) . . . . ?
C14 C13 C18 O3 179.8(2) . . . . ?
N1 C13 C18 O3 -2.5(3) . . . . ?
C14 C13 C18 C17 -0.2(3) . . . . ?
N1 C13 C18 C17 177.6(2) . . . . ?
C22 O6 C19 C1 178.12(15) . . . . ?
C22 O6 C19 C25 -63.39(19) . . . . ?
C22 O6 C19 C20 59.53(19) . . . . ?
C6 C1 C19 O6 147.02(19) . . . . ?
C2 C1 C19 O6 -34.3(2) . . . . ?
C6 C1 C19 C25 31.2(3) . . . . ?
C2 C1 C19 C25 -150.12(19) . . . . ?
C6 C1 C19 C20 -96.7(2) . . . . ?
C2 C1 C19 C20 82.0(2) . . . . ?
C13 N1 C20 C7 -35.6(2) . . . . ?
C21 N1 C20 C7 -166.47(16) . . . . ?
C13 N1 C20 C19 -166.43(15) . . . . ?
C21 N1 C20 C19 62.66(19) . . . . ?
C8 C7 C20 N1 128.6(2) . . . . ?
C12 C7 C20 N1 -53.1(3) . . . . ?
C8 C7 C20 C19 -104.0(2) . . . . ?
C12 C7 C20 C19 74.3(2) . . . . ?
O6 C19 C20 N1 -61.40(18) . . . . ?
C1 C19 C20 N1 -177.43(14) . . . . ?
C25 C19 C20 N1 56.6(2) . . . . ?
O6 C19 C20 C7 167.78(15) . . . . ?
C1 C19 C20 C7 51.7(2) . . . . ?
C25 C19 C20 C7 -74.2(2) . . . . ?
C13 N1 C21 C22 169.86(16) . . . . ?
C20 N1 C21 C22 -59.02(19) . . . . ?
C13 N1 C21 C23 49.1(2) . . . . ?
C20 N1 C21 C23 -179.79(16) . . . . ?
C19 O6 C22 C21 -59.3(2) . . . . ?
N1 C21 C22 O6 56.8(2) . . . . ?
C23 C21 C22 O6 178.14(16) . . . . ?
N1 C21 C23 C24 -169.40(17) . . . . ?
C22 C21 C23 C24 71.2(2) . . . . ?
C21 C23 C24 O5 -7.6(3) . . . . ?
C21 C23 C24 O4 172.92(19) . . . . ?
C26 O1 C25 O2 0.0(3) . . . . ?
C26 O1 C25 C19 177.64(18) . . . . ?
O6 C19 C25 O2 126.4(2) . . . . ?
C1 C19 C25 O2 -117.8(2) . . . . ?
C20 C19 C25 O2 8.1(3) . . . . ?
O6 C19 C25 O1 -51.1(2) . . . . ?
C1 C19 C25 O1 64.8(2) . . . . ?
C20 C19 C25 O1 -169.37(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.039
