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

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_OxmTBAF

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H82 F2 N6 O7'
_chemical_formula_weight         917.22

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   p21/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                   22.5699(14)
_cell_length_b                   9.4519(7)
_cell_length_c                   26.9700(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.307(3)
_cell_angle_gamma                90.00
_cell_volume                     5575.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9423
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      17.88

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.093
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1992
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   psi-scan

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            47277
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0572
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         0.93
_diffrn_reflns_theta_max         25.00
_reflns_number_total             9788
_reflns_number_gt                5798
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0200P)²+4.1036P] 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         9288
_refine_ls_number_parameters     583
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.2106
_refine_ls_R_factor_gt           0.0988
_refine_ls_wR_factor_ref         0.2032
_refine_ls_wR_factor_gt          0.1827
_refine_ls_goodness_of_fit_ref   1.359
_refine_ls_restrained_S_all      1.676
_refine_ls_shift/su_max          0.003
_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
C14 C 0.1661(3) 0.7657(10) 0.3159(3) 0.221(9) Uani 1 1 d GD . .
C15 C 0.1492(3) 0.6625(6) 0.3465(3) 0.214(8) Uani 1 1 d G . .
H15 H 0.1555 0.5674 0.3405 0.257 Uiso 1 1 calc R . .
C16 C 0.1228(3) 0.7013(7) 0.3859(3) 0.165(6) Uani 1 1 d G . .
H16 H 0.1115 0.6322 0.4063 0.198 Uiso 1 1 calc R . .
C17 C 0.1133(3) 0.8434(9) 0.3947(2) 0.221(10) Uani 1 1 d GD . .
C18 C 0.1302(3) 0.9467(6) 0.3642(3) 0.188(8) Uani 1 1 d G . .
C13 C 0.1566(3) 0.9078(8) 0.3248(3) 0.203(8) Uani 1 1 d G . .
C9 C 0.4068(3) 0.4408(8) 0.1007(2) 0.0737(17) Uani 1 1 d . . .
C5 C 0.3680(3) 0.6060(9) 0.1546(2) 0.088(2) Uani 1 1 d . . .
C8 C 0.4494(3) 0.5493(8) 0.0903(2) 0.0773(17) Uani 1 1 d . . .
C4 C 0.3670(3) 0.4671(8) 0.1321(2) 0.0764(17) Uani 1 1 d . . .
C6 C 0.4067(3) 0.7118(8) 0.1431(3) 0.100(2) Uani 1 1 d . . .
H6 H 0.4056 0.8021 0.1566 0.120 Uiso 1 1 calc R . .
C7 C 0.4452(3) 0.6850(8) 0.1132(3) 0.096(2) Uani 1 1 d . . .
H7 H 0.4703 0.7578 0.1071 0.115 Uiso 1 1 calc R . .
C1 C 0.3717(4) 0.2145(9) 0.0830(3) 0.100(2) Uani 1 1 d . . .
H1 H 0.3725 0.1285 0.0664 0.120 Uiso 1 1 calc R . .
C3 C 0.3282(3) 0.3542(10) 0.1384(2) 0.099(2) Uani 1 1 d . . .
H3 H 0.3012 0.3650 0.1592 0.119 Uiso 1 1 calc R . .
C2 C 0.3308(3) 0.2303(9) 0.1137(3) 0.107(2) Uani 1 1 d . . .
H2 H 0.3052 0.1558 0.1172 0.129 Uiso 1 1 calc R . .
C11 C 0.1601(9) 1.160(3) 0.3157(10) 0.270(19) Uani 1 1 d . . .
H11 H 0.1725 1.2368 0.2992 0.324 Uiso 1 1 calc R . .
C10 C 0.1320(8) 1.186(3) 0.3525(9) 0.248(15) Uani 1 1 d . . .
H10 H 0.1234 1.2800 0.3584 0.297 Uiso 1 1 calc R . .
C23 C 0.1098(2) 0.5420(6) 0.15959(19) 0.0760(17) Uani 1 1 d . . .
H23A H 0.1380 0.4631 0.1628 0.091 Uiso 1 1 calc R . .
H23B H 0.1278 0.6102 0.1858 0.091 Uiso 1 1 calc R . .
C19 C 0.1678(2) 0.6658(6) 0.1088(2) 0.0745(17) Uani 1 1 d . . .
H19A H 0.1807 0.7274 0.1383 0.089 Uiso 1 1 calc R . .
H19B H 0.1957 0.5860 0.1139 0.089 Uiso 1 1 calc R . .
C24 C 0.0507(3) 0.4880(7) 0.1705(2) 0.092(2) Uani 1 1 d . . .
H24A H 0.0225 0.5661 0.1692 0.111 Uiso 1 1 calc R . .
H24B H 0.0318 0.4195 0.1446 0.111 Uiso 1 1 calc R . .
C20 C 0.1743(2) 0.7460(7) 0.0618(2) 0.0872(19) Uani 1 1 d . . .
H20A H 0.1475 0.8278 0.0565 0.105 Uiso 1 1 calc R . .
H20B H 0.1625 0.6856 0.0320 0.105 Uiso 1 1 calc R . .
C25 C 0.0644(3) 0.4197(8) 0.2229(2) 0.113(3) Uani 1 1 d . . .
H25A H 0.0923 0.3414 0.2236 0.135 Uiso 1 1 calc R . .
H25B H 0.0847 0.4883 0.2482 0.135 Uiso 1 1 calc R . .
C21 C 0.2403(3) 0.7939(8) 0.0688(3) 0.108(2) Uani 1 1 d . . .
H21A H 0.2519 0.8513 0.0994 0.130 Uiso 1 1 calc R . .
H21B H 0.2665 0.7111 0.0739 0.130 Uiso 1 1 calc R . .
C22 C 0.2517(3) 0.8776(8) 0.0244(3) 0.133(3) Uani 1 1 d . . .
H22A H 0.2373 0.8251 -0.0067 0.200 Uiso 1 1 calc R . .
H22B H 0.2948 0.8949 0.0298 0.200 Uiso 1 1 calc R . .
H22C H 0.2304 0.9662 0.0219 0.200 Uiso 1 1 calc R . .
C26 C 0.0079(3) 0.3655(10) 0.2377(3) 0.149(4) Uani 1 1 d . . .
H26A H -0.0201 0.4423 0.2371 0.223 Uiso 1 1 calc R . .
H26B H 0.0193 0.3259 0.2715 0.223 Uiso 1 1 calc R . .
H26C H -0.0114 0.2941 0.2138 0.223 Uiso 1 1 calc R . .
C27 C 0.0578(2) 0.7304(7) 0.0985(2) 0.0842(18) Uani 1 1 d . . .
H27A H 0.0553 0.7705 0.0649 0.101 Uiso 1 1 calc R . .
H27B H 0.0179 0.6914 0.0982 0.101 Uiso 1 1 calc R . .
C28 C 0.0719(3) 0.8482(7) 0.1378(3) 0.114(2) Uani 1 1 d . . .
H28A H 0.1130 0.8835 0.1410 0.136 Uiso 1 1 calc R . .
H28B H 0.0688 0.8137 0.1709 0.136 Uiso 1 1 calc R . .
C29 C 0.0246(4) 0.9674(10) 0.1190(4) 0.174(4) Uani 1 1 d . . .
H29A H 0.0208 0.9843 0.0828 0.208 Uiso 1 1 calc R . .
H29B H -0.0151 0.9376 0.1231 0.208 Uiso 1 1 calc R . .
C30 C 0.0417(5) 1.0920(14) 0.1460(6) 0.275(7) Uani 1 1 d . . .
H30A H 0.0450 1.0757 0.1817 0.413 Uiso 1 1 calc R . .
H30B H 0.0115 1.1636 0.1337 0.413 Uiso 1 1 calc R . .
H30C H 0.0805 1.1228 0.1414 0.413 Uiso 1 1 calc R . .
C31 C 0.0814(2) 0.5063(6) 0.06407(19) 0.0774(17) Uani 1 1 d . . .
H31A H 0.0422 0.4695 0.0669 0.093 Uiso 1 1 calc R . .
H31B H 0.0745 0.5574 0.0320 0.093 Uiso 1 1 calc R . .
C32 C 0.1230(3) 0.3826(7) 0.0618(2) 0.0913(19) Uani 1 1 d . . .
H32A H 0.1323 0.3321 0.0941 0.110 Uiso 1 1 calc R . .
H32B H 0.1611 0.4161 0.0555 0.110 Uiso 1 1 calc R . .
C33 C 0.0907(4) 0.2843(8) 0.0186(3) 0.126(3) Uani 1 1 d . . .
H33A H 0.0536 0.2479 0.0260 0.151 Uiso 1 1 calc R . .
H33B H 0.0792 0.3374 -0.0132 0.151 Uiso 1 1 calc R . .
C34 C 0.1305(4) 0.1647(10) 0.0123(4) 0.188(4) Uani 1 1 d . . .
H34A H 0.1682 0.2007 0.0068 0.281 Uiso 1 1 calc R . .
H34B H 0.1102 0.1086 -0.0166 0.281 Uiso 1 1 calc R . .
H34C H 0.1390 0.1073 0.0426 0.281 Uiso 1 1 calc R . .
C39 C 0.4362(2) 0.7779(6) 0.8651(2) 0.0804(17) Uani 1 1 d . . .
H39A H 0.4516 0.8436 0.8930 0.096 Uiso 1 1 calc R . .
H39B H 0.4628 0.6957 0.8708 0.096 Uiso 1 1 calc R . .
C40 C 0.4401(3) 0.8481(7) 0.8151(2) 0.096(2) Uani 1 1 d . . .
H40A H 0.4286 0.7799 0.7875 0.116 Uiso 1 1 calc R . .
H40B H 0.4111 0.9257 0.8078 0.116 Uiso 1 1 calc R . .
C35 C 0.3284(3) 0.8575(7) 0.8595(2) 0.097(2) Uani 1 1 d . . .
H35A H 0.3250 0.8956 0.8255 0.117 Uiso 1 1 calc R . .
H35B H 0.2882 0.8239 0.8607 0.117 Uiso 1 1 calc R . .
C41 C 0.5026(3) 0.9030(8) 0.8170(3) 0.117(2) Uani 1 1 d . . .
H41A H 0.5310 0.8242 0.8222 0.140 Uiso 1 1 calc R . .
H41B H 0.5151 0.9657 0.8462 0.140 Uiso 1 1 calc R . .
C36 C 0.3460(4) 0.9750(9) 0.8972(3) 0.140(3) Uani 1 1 d . . .
H36A H 0.3843 1.0168 0.8944 0.168 Uiso 1 1 calc R . .
H36B H 0.3514 0.9390 0.9317 0.168 Uiso 1 1 calc R . .
C42 C 0.5066(3) 0.9817(8) 0.7694(3) 0.122(3) Uani 1 1 d . . .
H42A H 0.4945 0.9202 0.7403 0.183 Uiso 1 1 calc R . .
H42B H 0.5479 1.0126 0.7727 0.183 Uiso 1 1 calc R . .
H42C H 0.4800 1.0624 0.7648 0.183 Uiso 1 1 calc R . .
C37 C 0.2950(5) 1.0872(11) 0.8859(4) 0.179(4) Uani 1 1 d . . .
H37 H 0.2646 1.0907 0.8555 0.214 Uiso 1 1 calc R . .
C38 C 0.2984(6) 1.1714(16) 0.9210(4) 0.289(9) Uani 1 1 d . . .
H38A H 0.3297 1.1632 0.9506 0.347 Uiso 1 1 calc R . .
H38B H 0.2697 1.2435 0.9180 0.347 Uiso 1 1 calc R . .
C43 C 0.3457(2) 0.6260(7) 0.8241(2) 0.0811(18) Uani 1 1 d . . .
H43A H 0.3045 0.6016 0.8256 0.097 Uiso 1 1 calc R . .
H43B H 0.3430 0.6725 0.7915 0.097 Uiso 1 1 calc R . .
C44 C 0.3818(3) 0.4909(7) 0.8253(2) 0.0906(19) Uani 1 1 d . . .
H44A H 0.4216 0.5127 0.8197 0.109 Uiso 1 1 calc R . .
H44B H 0.3880 0.4473 0.8588 0.109 Uiso 1 1 calc R . .
C45 C 0.3489(3) 0.3886(8) 0.7849(3) 0.110(2) Uani 1 1 d . . .
H45A H 0.3092 0.3670 0.7907 0.132 Uiso 1 1 calc R . .
H45B H 0.3424 0.4330 0.7515 0.132 Uiso 1 1 calc R . .
C46 C 0.3840(3) 0.2529(8) 0.7849(3) 0.129(3) Uani 1 1 d . . .
H46A H 0.4219 0.2728 0.7762 0.194 Uiso 1 1 calc R . .
H46B H 0.3602 0.1889 0.7602 0.194 Uiso 1 1 calc R . .
H46C H 0.3922 0.2107 0.8183 0.194 Uiso 1 1 calc R . .
C47 C 0.3767(2) 0.6634(7) 0.9190(2) 0.0801(17) Uani 1 1 d . . .
H47A H 0.3925 0.7332 0.9453 0.096 Uiso 1 1 calc R . .
H47B H 0.4061 0.5868 0.9234 0.096 Uiso 1 1 calc R . .
C48 C 0.3163(3) 0.6048(7) 0.9273(2) 0.0884(19) Uani 1 1 d . . .
H48A H 0.2862 0.6802 0.9225 0.106 Uiso 1 1 calc R . .
H48B H 0.3008 0.5320 0.9020 0.106 Uiso 1 1 calc R . .
C49 C 0.3251(3) 0.5439(8) 0.9799(2) 0.097(2) Uani 1 1 d . . .
H49A H 0.3404 0.6171 1.0050 0.117 Uiso 1 1 calc R . .
H49B H 0.3556 0.4695 0.9846 0.117 Uiso 1 1 calc R . .
C50 C 0.2659(3) 0.4837(8) 0.9889(2) 0.111(2) Uani 1 1 d . . .
H50A H 0.2351 0.5560 0.9829 0.167 Uiso 1 1 calc R . .
H50B H 0.2730 0.4511 1.0236 0.167 Uiso 1 1 calc R . .
H50C H 0.2524 0.4060 0.9660 0.167 Uiso 1 1 calc R . .
N1 N 0.4091(2) 0.3148(7) 0.07633(18) 0.0856(15) Uani 1 1 d . . .
N2 N 0.3287(3) 0.6247(8) 0.1848(2) 0.116(2) Uani 1 1 d . . .
C12 C 0.1155(4) 1.0899(14) 0.3809(4) 0.153(5) Uani 1 1 d . . .
H12 H 0.0973 1.1079 0.4077 0.184 Uiso 1 1 calc R . .
N5 N 0.10426(18) 0.6107(5) 0.10760(16) 0.0677(12) Uani 1 1 d . . .
N6 N 0.37173(19) 0.7312(5) 0.86694(17) 0.0737(13) Uani 1 1 d . . .
O1 O 0.48558(19) 0.5257(5) 0.06334(16) 0.0999(14) Uani 1 1 d . . .
N4 N 0.0834(4) 0.8997(9) 0.4294(3) 0.171(5) Uani 1 1 d D . .
O2 O 0.3277(2) 0.7485(8) 0.2043(2) 0.143(2) Uani 1 1 d . . .
H2A H 0.3590 0.7912 0.2034 0.215 Uiso 1 1 calc R . .
F1 F 0.5294(2) 0.7415(5) 0.00788(17) 0.1546(17) Uani 1 1 d . . .
F2 F 0.22527(18) 0.9098(5) 0.20631(16) 0.1553(18) Uani 1 1 d . . .
O5 O 0.2517(2) 0.4733(5) 0.23922(17) 0.1284(17) Uani 1 1 d . . .
O6 O 0.2032(2) 0.2129(6) 0.1816(2) 0.156(2) Uani 1 1 d . . .
O4 O 0.0644(4) 0.8092(12) 0.4529(3) 0.262(5) Uani 1 1 d D . .
H4 H 0.0917 0.7847 0.4775 0.393 Uiso 1 1 calc RD . .
O7 O 0.4549(6) 0.9712(11) 0.0228(4) 0.389(7) Uani 1 1 d . . .
N3 N 0.1732(4) 1.0160(15) 0.2991(4) 0.192(5) Uani 1 1 d . . .
O3 O 0.1857(2) 0.6830(10) 0.2807(2) 0.194(4) Uani 1 1 d 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
C14 C15 1.3900 . ?
C14 C13 1.3900 . ?
C14 O3 1.384(6) . ?
C15 C16 1.3900 . ?
C16 C17 1.3900 . ?
C17 C18 1.3900 . ?
C17 N4 1.388(9) . ?
C18 C13 1.3900 . ?
C18 C12 1.490(15) . ?
C13 N3 1.338(11) . ?
C9 N1 1.367(7) . ?
C9 C4 1.403(7) . ?
C9 C8 1.478(8) . ?
C5 N2 1.355(8) . ?
C5 C6 1.412(9) . ?
C5 C4 1.444(9) . ?
C8 O1 1.241(6) . ?
C8 C7 1.437(8) . ?
C4 C3 1.416(9) . ?
C6 C7 1.348(8) . ?
C1 N1 1.312(8) . ?
C1 C2 1.391(8) . ?
C3 C2 1.356(9) . ?
C11 C10 1.33(3) . ?
C11 N3 1.48(2) . ?
C10 C12 1.30(2) . ?
C23 C24 1.521(7) . ?
C23 N5 1.522(6) . ?
C19 C20 1.515(7) . ?
C19 N5 1.519(6) . ?
C24 C25 1.516(7) . ?
C20 C21 1.524(7) . ?
C25 C26 1.516(8) . ?
C21 C22 1.508(8) . ?
C27 C28 1.516(8) . ?
C27 N5 1.521(6) . ?
C28 C29 1.548(10) . ?
C29 C30 1.389(13) . ?
C31 C32 1.510(7) . ?
C31 N5 1.523(6) . ?
C32 C33 1.528(8) . ?
C33 C34 1.480(9) . ?
C39 C40 1.524(7) . ?
C39 N6 1.534(6) . ?
C40 C41 1.492(8) . ?
C35 C36 1.493(9) . ?
C35 N6 1.525(7) . ?
C41 C42 1.507(8) . ?
C36 C37 1.540(10) . ?
C37 C38 1.225(11) . ?
C43 C44 1.510(8) . ?
C43 N6 1.528(7) . ?
C44 C45 1.508(8) . ?
C45 C46 1.508(9) . ?
C47 N6 1.523(6) . ?
C47 C48 1.538(7) . ?
C48 C49 1.498(7) . ?
C49 C50 1.527(7) . ?
N2 O2 1.286(7) . ?
N4 O4 1.204(9) . ?

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
C15 C14 C13 120.0 . . ?
C15 C14 O3 101.0(8) . . ?
C13 C14 O3 138.8(8) . . ?
C14 C15 C16 120.0 . . ?
C17 C16 C15 120.0 . . ?
C16 C17 C18 120.0 . . ?
C16 C17 N4 127.4(6) . . ?
C18 C17 N4 112.4(6) . . ?
C17 C18 C13 120.0 . . ?
C17 C18 C12 110.1(7) . . ?
C13 C18 C12 129.9(7) . . ?
N3 C13 C18 114.9(8) . . ?
N3 C13 C14 125.1(8) . . ?
C18 C13 C14 120.0 . . ?
N1 C9 C4 123.4(6) . . ?
N1 C9 C8 114.2(6) . . ?
C4 C9 C8 122.4(7) . . ?
N2 C5 C6 124.9(8) . . ?
N2 C5 C4 115.2(8) . . ?
C6 C5 C4 119.9(6) . . ?
O1 C8 C7 122.4(7) . . ?
O1 C8 C9 122.6(6) . . ?
C7 C8 C9 115.0(6) . . ?
C9 C4 C3 116.5(7) . . ?
C9 C4 C5 118.0(7) . . ?
C3 C4 C5 125.5(7) . . ?
C7 C6 C5 121.6(7) . . ?
C6 C7 C8 123.0(7) . . ?
N1 C1 C2 123.2(7) . . ?
C2 C3 C4 119.3(7) . . ?
C3 C2 C1 120.0(7) . . ?
C10 C11 N3 124(3) . . ?
C12 C10 C11 125(3) . . ?
C24 C23 N5 116.4(4) . . ?
C20 C19 N5 116.0(4) . . ?
C25 C24 C23 109.7(5) . . ?
C19 C20 C21 109.9(5) . . ?
C26 C25 C24 113.5(5) . . ?
C22 C21 C20 114.3(6) . . ?
C28 C27 N5 114.6(5) . . ?
C27 C28 C29 107.2(6) . . ?
C30 C29 C28 111.4(8) . . ?
C32 C31 N5 115.9(4) . . ?
C31 C32 C33 108.5(5) . . ?
C34 C33 C32 111.2(7) . . ?
C40 C39 N6 114.6(4) . . ?
C41 C40 C39 112.4(5) . . ?
C36 C35 N6 116.0(5) . . ?
C40 C41 C42 113.5(6) . . ?
C35 C36 C37 108.5(7) . . ?
C38 C37 C36 113.1(10) . . ?
C44 C43 N6 115.4(4) . . ?
C45 C44 C43 111.1(5) . . ?
C46 C45 C44 112.4(6) . . ?
N6 C47 C48 114.8(4) . . ?
C49 C48 C47 111.1(5) . . ?
C48 C49 C50 112.2(5) . . ?
C1 N1 C9 117.5(6) . . ?
O2 N2 C5 116.4(7) . . ?
C10 C12 C18 109.8(16) . . ?
C19 N5 C27 111.0(4) . . ?
C19 N5 C23 105.3(4) . . ?
C27 N5 C23 111.3(4) . . ?
C19 N5 C31 112.2(4) . . ?
C27 N5 C31 105.6(4) . . ?
C23 N5 C31 111.6(4) . . ?
C47 N6 C35 110.5(4) . . ?
C47 N6 C43 110.6(4) . . ?
C35 N6 C43 107.2(4) . . ?
C47 N6 C39 107.3(4) . . ?
C35 N6 C39 110.7(5) . . ?
C43 N6 C39 110.7(4) . . ?
O4 N4 C17 112.1(10) . . ?
C13 N3 C11 116.3(14) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 1024294'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_znoxm

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 N4 O6 Zn'
_chemical_formula_weight         447.70

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'
Zn Zn 0.2839 1.4301 '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                   7.2755(9)
_cell_length_b                   7.9392(9)
_cell_length_c                   8.4103(9)
_cell_angle_alpha                64.840(11)
_cell_angle_beta                 74.394(10)
_cell_angle_gamma                87.012(10)
_cell_volume                     422.41(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1193
_cell_measurement_theta_min      2.9082
_cell_measurement_theta_max      28.6931

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             228
_exptl_absorpt_coefficient_mu    1.503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.655
_exptl_absorpt_correction_T_max  0.740
_exptl_absorpt_process_details   psi-scan

_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  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2958
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0585
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         25.25
_reflns_number_total             1533
_reflns_number_gt                1297
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0110P)²+0.6638P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1533
_refine_ls_number_parameters     138
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.0790
_refine_ls_wR_factor_gt          0.0724
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_restrained_S_all      0.924
_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
Zn1 Zn 0.5000 0.5000 1.0000 0.0429(2) Uani 1 2 d S . .
O1 O 0.3927(4) 0.2671(3) 0.9857(3) 0.0450(7) Uani 1 1 d . . .
N1 N 0.6040(4) 0.6733(4) 0.7238(4) 0.0352(7) Uani 1 1 d . . .
O2 O 0.9489(4) 1.4491(3) 0.3187(3) 0.0529(7) Uani 1 1 d . . .
O3 O 0.2216(4) 0.6244(4) 0.9990(3) 0.0463(7) Uani 1 1 d D . .
H3B H 0.1409 0.5630 1.1017 0.070 Uiso 1 1 d R . .
C9 C 0.6733(4) 0.8435(4) 0.6947(4) 0.0290(7) Uani 1 1 d . . .
N2 N 0.8826(4) 1.2985(4) 0.3314(4) 0.0399(7) Uani 1 1 d . . .
C7 C 0.7449(5) 1.0413(5) 0.8329(5) 0.0390(9) Uani 1 1 d . . .
H7 H 0.7486 1.0608 0.9335 0.047 Uiso 1 1 calc R . .
C8 C 0.6695(5) 0.8648(5) 0.8599(5) 0.0356(8) Uani 1 1 d . . .
C6 C 0.8105(5) 1.1791(5) 0.6636(5) 0.0377(9) Uani 1 1 d . . .
H6 H 0.8559 1.2923 0.6521 0.045 Uiso 1 1 calc R . .
C4 C 0.7444(4) 0.9881(4) 0.5187(4) 0.0303(8) Uani 1 1 d . . .
C5 C 0.8141(5) 1.1614(5) 0.5040(5) 0.0326(8) Uani 1 1 d . . .
C2 C 0.6806(5) 0.7738(5) 0.4030(5) 0.0388(9) Uani 1 1 d . . .
H2 H 0.6835 0.7454 0.3059 0.047 Uiso 1 1 calc R . .
C1 C 0.6092(5) 0.6404(5) 0.5825(5) 0.0416(9) Uani 1 1 d . . .
H1 H 0.5635 0.5238 0.6028 0.050 Uiso 1 1 calc R . .
C3 C 0.7459(5) 0.9458(5) 0.3714(5) 0.0368(8) Uani 1 1 d . . .
H3 H 0.7919 1.0360 0.2521 0.044 Uiso 1 1 calc R . .
H3A H 0.190(5) 0.631(5) 0.908(4) 0.061(14) Uiso 1 1 d 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
Zn1 N1 2.075(3) . ?
Zn1 N1 2.075(3) 2_667 ?
Zn1 O1 2.105(2) . ?
Zn1 O1 2.105(2) 2_667 ?
Zn1 O3 2.207(3) . ?
Zn1 O3 2.207(3) 2_667 ?
O1 C8 1.251(4) 2_667 ?
N1 C1 1.311(4) . ?
N1 C9 1.365(4) . ?
O2 N2 1.264(3) . ?
C9 C4 1.408(4) . ?
C9 C8 1.462(4) . ?
N2 C5 1.365(4) . ?
C7 C6 1.347(5) . ?
C7 C8 1.435(4) . ?
C8 O1 1.251(4) 2_667 ?
C6 C5 1.402(5) . ?
C4 C3 1.412(4) . ?
C4 C5 1.435(4) . ?
C2 C3 1.362(4) . ?
C2 C1 1.395(5) . ?

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 Zn1 N1 180.0 . 2_667 ?
N1 Zn1 O1 100.07(9) . . ?
N1 Zn1 O1 79.93(9) 2_667 . ?
N1 Zn1 O1 79.93(9) . 2_667 ?
N1 Zn1 O1 100.07(9) 2_667 2_667 ?
O1 Zn1 O1 179.999(1) . 2_667 ?
N1 Zn1 O3 89.71(10) . . ?
N1 Zn1 O3 90.29(10) 2_667 . ?
O1 Zn1 O3 90.81(10) . . ?
O1 Zn1 O3 89.19(10) 2_667 . ?
N1 Zn1 O3 90.29(10) . 2_667 ?
N1 Zn1 O3 89.71(10) 2_667 2_667 ?
O1 Zn1 O3 89.19(10) . 2_667 ?
O1 Zn1 O3 90.81(10) 2_667 2_667 ?
O3 Zn1 O3 180.0 . 2_667 ?
C8 O1 Zn1 112.2(2) 2_667 . ?
C1 N1 C9 118.9(3) . . ?
C1 N1 Zn1 129.2(2) . . ?
C9 N1 Zn1 111.9(2) . . ?
N1 C9 C4 122.6(3) . . ?
N1 C9 C8 115.1(3) . . ?
C4 C9 C8 122.2(3) . . ?
O2 N2 C5 116.4(3) . . ?
C6 C7 C8 120.9(3) . . ?
O1 C8 C7 123.1(3) 2_667 . ?
O1 C8 C9 120.7(3) 2_667 . ?
C7 C8 C9 116.2(3) . . ?
C7 C6 C5 123.6(3) . . ?
C9 C4 C3 116.1(3) . . ?
C9 C4 C5 118.0(3) . . ?
C3 C4 C5 125.9(3) . . ?
N2 C5 C6 124.4(3) . . ?
N2 C5 C4 116.5(3) . . ?
C6 C5 C4 119.1(3) . . ?
C3 C2 C1 119.4(3) . . ?
N1 C1 C2 122.5(3) . . ?
C2 C3 C4 120.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 983710'
