# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
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data_wwhc27

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H16 O3'
_chemical_formula_weight         208.25

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthrohombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   6.687(2)
_cell_length_b                   19.034(7)
_cell_length_c                   35.511(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4520(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1792
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   Multiscan
_exptl_absorpt_correction_T_min  0.5613
_exptl_absorpt_correction_T_max  0.7456
_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  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47879
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_sigmaI/netI    0.0666
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.15
_diffrn_reflns_theta_max         25.00
_reflns_number_total             7936
_reflns_number_gt                4246
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS 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)+(0.0655P)²+0.5531P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0033(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.3(13)
_refine_ls_number_reflns         7936
_refine_ls_number_parameters     542
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1449
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_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 1.2563(5) 0.31065(18) 0.56359(8) 0.0836(9) Uani 1 1 d . . .
O2 O 1.1136(4) 0.39978(13) 0.45390(7) 0.0608(7) Uani 1 1 d . . .
O3 O 1.3108(4) 0.31582(14) 0.47836(7) 0.0577(7) Uani 1 1 d . . .
O4 O 1.4107(5) 0.85560(15) 0.46756(8) 0.0777(9) Uani 1 1 d . . .
O5 O 1.2493(5) 0.64947(13) 0.42377(7) 0.0649(8) Uani 1 1 d . . .
O6 O 1.4439(4) 0.69442(14) 0.46932(7) 0.0621(7) Uani 1 1 d . . .
C1 C 1.1787(6) 0.3430(2) 0.53820(12) 0.0541(11) Uani 1 1 d . . .
C2 C 1.1152(6) 0.4192(2) 0.53915(11) 0.0595(11) Uani 1 1 d . . .
H2A H 1.2223 0.4473 0.5278 0.071 Uiso 1 1 calc R . .
C3 C 1.0705(7) 0.4494(3) 0.57807(13) 0.0815(14) Uani 1 1 d . . .
H3A H 1.0390 0.4989 0.5758 0.098 Uiso 1 1 calc R . .
H3B H 1.1882 0.4450 0.5939 0.098 Uiso 1 1 calc R . .
C4 C 0.8954(8) 0.4111(2) 0.59653(12) 0.0790(13) Uani 1 1 d . . .
H4A H 0.9439 0.3681 0.6079 0.095 Uiso 1 1 calc R . .
H4B H 0.8412 0.4404 0.6164 0.095 Uiso 1 1 calc R . .
C5 C 0.7330(7) 0.3937(2) 0.56947(13) 0.0691(12) Uani 1 1 d . . .
H5A H 0.6120 0.3778 0.5792 0.083 Uiso 1 1 calc R . .
C6 C 0.7492(6) 0.3994(2) 0.53302(13) 0.0671(12) Uani 1 1 d . . .
H6A H 0.6363 0.3899 0.5186 0.080 Uiso 1 1 calc R . .
C7 C 0.9376(6) 0.4201(2) 0.51243(11) 0.0593(11) Uani 1 1 d . . .
H7A H 0.9220 0.4670 0.5014 0.071 Uiso 1 1 calc R . .
C8 C 0.9898(6) 0.3670(2) 0.48197(11) 0.0563(11) Uani 1 1 d . . .
H8A H 0.8706 0.3451 0.4710 0.068 Uiso 1 1 calc R . .
C9 C 1.2661(6) 0.3506(2) 0.44394(10) 0.0519(10) Uani 1 1 d . . .
C10 C 1.1915(7) 0.2987(2) 0.41516(11) 0.0762(14) Uani 1 1 d . . .
H10A H 1.0756 0.2750 0.4248 0.114 Uiso 1 1 calc R . .
H10B H 1.2945 0.2650 0.4099 0.114 Uiso 1 1 calc R . .
H10C H 1.1570 0.3231 0.3924 0.114 Uiso 1 1 calc R . .
C11 C 1.4468(6) 0.3898(2) 0.43113(11) 0.0692(13) Uani 1 1 d . . .
H11A H 1.4880 0.4220 0.4504 0.104 Uiso 1 1 calc R . .
H11B H 1.4159 0.4154 0.4086 0.104 Uiso 1 1 calc R . .
H11C H 1.5531 0.3572 0.4261 0.104 Uiso 1 1 calc R . .
C12 C 1.1303(6) 0.3128(2) 0.50008(10) 0.0502(10) Uani 1 1 d . . .
H12A H 1.0725 0.2656 0.5014 0.060 Uiso 1 1 calc R . .
C13 C 1.3286(6) 0.8082(2) 0.45118(11) 0.0510(10) Uani 1 1 d . . .
C14 C 1.2675(6) 0.8070(2) 0.40981(10) 0.0536(10) Uani 1 1 d . . .
H14A H 1.3727 0.7835 0.3953 0.064 Uiso 1 1 calc R . .
C15 C 1.2330(8) 0.8792(2) 0.39321(12) 0.0765(13) Uani 1 1 d . . .
H15A H 1.1995 0.8746 0.3667 0.092 Uiso 1 1 calc R . .
H15B H 1.3552 0.9065 0.3951 0.092 Uiso 1 1 calc R . .
C16 C 1.0646(8) 0.9181(2) 0.41348(13) 0.0754(13) Uani 1 1 d . . .
H16A H 1.1159 0.9381 0.4367 0.091 Uiso 1 1 calc R . .
H16B H 1.0178 0.9563 0.3977 0.091 Uiso 1 1 calc R . .
C17 C 0.8938(7) 0.8706(3) 0.42236(12) 0.0766(14) Uani 1 1 d . . .
H17A H 0.7742 0.8914 0.4297 0.092 Uiso 1 1 calc R . .
C18 C 0.8990(7) 0.8017(3) 0.42059(11) 0.0681(12) Uani 1 1 d . . .
H18A H 0.7821 0.7772 0.4260 0.082 Uiso 1 1 calc R . .
C19 C 1.0817(6) 0.7599(2) 0.41035(11) 0.0576(11) Uani 1 1 d . . .
H19A H 1.0633 0.7378 0.3857 0.069 Uiso 1 1 calc R . .
C20 C 1.1275(6) 0.7041(2) 0.44008(10) 0.0562(11) Uani 1 1 d . . .
H20A H 1.0059 0.6855 0.4518 0.067 Uiso 1 1 calc R . .
C21 C 1.3916(6) 0.6299(2) 0.45093(11) 0.0539(10) Uani 1 1 d . . .
C22 C 1.5773(7) 0.6031(2) 0.43134(13) 0.0762(14) Uani 1 1 d . . .
H22A H 1.6260 0.6382 0.4143 0.114 Uiso 1 1 calc R . .
H22B H 1.5454 0.5611 0.4176 0.114 Uiso 1 1 calc R . .
H22C H 1.6783 0.5928 0.4497 0.114 Uiso 1 1 calc R . .
C23 C 1.3075(7) 0.5773(2) 0.47879(12) 0.0748(14) Uani 1 1 d . . .
H23A H 1.1912 0.5968 0.4907 0.112 Uiso 1 1 calc R . .
H23B H 1.4066 0.5669 0.4975 0.112 Uiso 1 1 calc R . .
H23C H 1.2715 0.5350 0.4658 0.112 Uiso 1 1 calc R . .
C24 C 1.2689(6) 0.73818(19) 0.46887(10) 0.0497(10) Uani 1 1 d . . .
H24A H 1.2080 0.7436 0.4938 0.060 Uiso 1 1 calc R . .
O4' O 0.2758(5) 0.40229(17) 0.32809(8) 0.0852(10) Uani 1 1 d . . .
O5' O 0.1235(5) 0.51809(15) 0.22910(8) 0.0731(9) Uani 1 1 d . . .
O6' O 0.2991(4) 0.42163(13) 0.24364(7) 0.0627(8) Uani 1 1 d . . .
C13' C 0.1908(6) 0.4410(2) 0.30620(11) 0.0519(10) Uani 1 1 d . . .
C14' C 0.1312(7) 0.5162(2) 0.31319(11) 0.0608(12) Uani 1 1 d . . .
H14B H 0.2364 0.5467 0.3031 0.073 Uiso 1 1 calc R . .
C15' C 0.0969(9) 0.5358(3) 0.35408(14) 0.0932(16) Uani 1 1 d . . .
H15C H 0.0641 0.5853 0.3558 0.112 Uiso 1 1 calc R . .
H15D H 0.2188 0.5278 0.3683 0.112 Uiso 1 1 calc R . .
C16' C -0.0720(8) 0.4926(3) 0.37119(13) 0.0900(16) Uani 1 1 d . . .
H16C H -0.0213 0.4466 0.3781 0.108 Uiso 1 1 calc R . .
H16D H -0.1185 0.5155 0.3940 0.108 Uiso 1 1 calc R . .
C17' C -0.2426(8) 0.4840(3) 0.34489(15) 0.0848(15) Uani 1 1 d . . .
H17B H -0.3632 0.4680 0.3547 0.102 Uiso 1 1 calc R . .
C18' C -0.2345(7) 0.4975(2) 0.30858(15) 0.0789(14) Uani 1 1 d . . .
H18B H -0.3492 0.4897 0.2944 0.095 Uiso 1 1 calc R . .
C19' C -0.0538(7) 0.5245(2) 0.28863(12) 0.0645(12) Uani 1 1 d . . .
H19B H -0.0724 0.5739 0.2816 0.077 Uiso 1 1 calc R . .
C20' C -0.0053(6) 0.4806(2) 0.25391(12) 0.0630(12) Uani 1 1 d . . .
H20B H -0.1264 0.4641 0.2411 0.076 Uiso 1 1 calc R . .
C21' C 0.2622(7) 0.4700(2) 0.21343(11) 0.0632(11) Uani 1 1 d . . .
C22' C 0.4537(8) 0.5075(3) 0.20427(14) 0.0888(16) Uani 1 1 d . . .
H22D H 0.5023 0.5311 0.2264 0.133 Uiso 1 1 calc R . .
H22E H 0.4297 0.5414 0.1847 0.133 Uiso 1 1 calc R . .
H22F H 0.5515 0.4741 0.1958 0.133 Uiso 1 1 calc R . .
C23' C 0.1754(9) 0.4318(3) 0.18004(12) 0.112(2) Uani 1 1 d . . .
H23D H 0.0529 0.4092 0.1873 0.168 Uiso 1 1 calc R . .
H23E H 0.2688 0.3970 0.1714 0.168 Uiso 1 1 calc R . .
H23F H 0.1492 0.4647 0.1602 0.168 Uiso 1 1 calc R . .
C24' C 0.1259(6) 0.4196(2) 0.26723(10) 0.0524(10) Uani 1 1 d . . .
H24B H 0.0569 0.3742 0.2667 0.063 Uiso 1 1 calc R . .
O1' O 0.7221(5) 0.31169(17) 0.20371(8) 0.0780(9) Uani 1 1 d . . .
O2' O 0.5748(4) 0.19769(13) 0.30857(7) 0.0552(7) Uani 1 1 d . . .
O3' O 0.7992(4) 0.27649(13) 0.28751(7) 0.0534(7) Uani 1 1 d . . .
C1' C 0.6499(5) 0.2733(2) 0.22737(11) 0.0522(10) Uani 1 1 d . . .
C2' C 0.5752(6) 0.1991(2) 0.22144(10) 0.0505(10) Uani 1 1 d . . .
H2'A H 0.6785 0.1664 0.2302 0.061 Uiso 1 1 calc R . .
C3' C 0.5219(6) 0.1804(3) 0.18110(11) 0.0722(13) Uani 1 1 d . . .
H3'A H 0.4844 0.1313 0.1799 0.087 Uiso 1 1 calc R . .
H3'B H 0.6384 0.1871 0.1652 0.087 Uiso 1 1 calc R . .
C4' C 0.3500(6) 0.2253(3) 0.16620(11) 0.0756(14) Uani 1 1 d . . .
H4'A H 0.4023 0.2705 0.1582 0.091 Uiso 1 1 calc R . .
H4'B H 0.2925 0.2025 0.1443 0.091 Uiso 1 1 calc R . .
C5' C 0.1906(6) 0.2369(2) 0.19455(12) 0.0634(12) Uani 1 1 d . . .
H5'A H 0.0688 0.2545 0.1862 0.076 Uiso 1 1 calc R . .
C6' C 0.2102(6) 0.22377(19) 0.23087(11) 0.0553(10) Uani 1 1 d . . .
H6'A H 0.1009 0.2324 0.2464 0.066 Uiso 1 1 calc R . .
C7' C 0.3985(5) 0.19572(19) 0.24882(9) 0.0472(9) Uani 1 1 d . . .
H7'A H 0.3773 0.1471 0.2569 0.057 Uiso 1 1 calc R . .
C8' C 0.4656(5) 0.24079(19) 0.28266(9) 0.0445(9) Uani 1 1 d . . .
H8'A H 0.3520 0.2640 0.2949 0.053 Uiso 1 1 calc R . .
C9' C 0.7458(6) 0.2371(2) 0.32034(10) 0.0502(10) Uani 1 1 d . . .
C10' C 0.6937(7) 0.2859(2) 0.35227(11) 0.0712(13) Uani 1 1 d . . .
H10D H 0.5881 0.3168 0.3445 0.107 Uiso 1 1 calc R . .
H10E H 0.8093 0.3131 0.3590 0.107 Uiso 1 1 calc R . .
H10F H 0.6506 0.2589 0.3736 0.107 Uiso 1 1 calc R . .
C11' C 0.9123(7) 0.1866(2) 0.32969(12) 0.0742(13) Uani 1 1 d . . .
H11D H 0.9401 0.1576 0.3082 0.111 Uiso 1 1 calc R . .
H11E H 0.8726 0.1574 0.3505 0.111 Uiso 1 1 calc R . .
H11F H 1.0302 0.2125 0.3364 0.111 Uiso 1 1 calc R . .
C12' C 0.6178(5) 0.29366(19) 0.26806(9) 0.0451(9) Uani 1 1 d . . .
H12B H 0.5763 0.3427 0.2714 0.054 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 C1 1.209(4) . ?
O2 C9 1.428(4) . ?
O2 C8 1.438(4) . ?
O3 C9 1.423(4) . ?
O3 C12 1.433(4) . ?
O4 C13 1.206(4) . ?
O5 C21 1.405(5) . ?
O5 C20 1.442(4) . ?
O6 C21 1.433(4) . ?
O6 C24 1.436(4) . ?
C1 C12 1.506(5) . ?
C1 C2 1.511(6) . ?
C2 C7 1.520(5) . ?
C2 C3 1.526(6) . ?
C3 C4 1.527(6) . ?
C4 C5 1.488(6) . ?
C5 C6 1.303(5) . ?
C6 C7 1.509(6) . ?
C7 C8 1.521(5) . ?
C8 C12 1.536(5) . ?
C9 C11 1.491(5) . ?
C9 C10 1.506(5) . ?
C13 C14 1.525(5) . ?
C13 C24 1.526(5) . ?
C14 C15 1.513(5) . ?
C14 C19 1.533(5) . ?
C15 C16 1.527(6) . ?
C16 C17 1.490(7) . ?
C17 C18 1.314(6) . ?
C18 C19 1.502(6) . ?
C19 C20 1.529(5) . ?
C20 C24 1.537(5) . ?
C21 C22 1.512(5) . ?
C21 C23 1.516(5) . ?
O4' C13' 1.212(4) . ?
O5' C21' 1.417(5) . ?
O5' C20' 1.424(5) . ?
O6' C24' 1.430(4) . ?
O6' C21' 1.435(5) . ?
C13' C24' 1.506(5) . ?
C13' C14' 1.508(5) . ?
C14' C15' 1.516(6) . ?
C14' C19' 1.522(6) . ?
C15' C16' 1.524(7) . ?
C16' C17' 1.483(7) . ?
C17' C18' 1.316(6) . ?
C18' C19' 1.492(6) . ?
C19' C20' 1.525(6) . ?
C20' C24' 1.530(5) . ?
C21' C22' 1.502(6) . ?
C21' C23' 1.507(6) . ?
O1' C1' 1.213(4) . ?
O2' C9' 1.430(4) . ?
O2' C8' 1.433(4) . ?
O3' C9' 1.431(4) . ?
O3' C12' 1.434(4) . ?
C1' C12' 1.511(5) . ?
C1' C2' 1.513(5) . ?
C2' C3' 1.518(5) . ?
C2' C7' 1.532(5) . ?
C3' C4' 1.527(5) . ?
C4' C5' 1.483(6) . ?
C5' C6' 1.320(5) . ?
C6' C7' 1.509(5) . ?
C7' C8' 1.543(5) . ?
C8' C12' 1.522(5) . ?
C9' C10' 1.507(5) . ?
C9' C11' 1.508(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
C9 O2 C8 107.4(3) . . ?
C9 O3 C12 107.7(3) . . ?
C21 O5 C20 107.3(3) . . ?
C21 O6 C24 107.0(3) . . ?
O1 C1 C12 124.6(4) . . ?
O1 C1 C2 126.4(4) . . ?
C12 C1 C2 109.0(3) . . ?
C1 C2 C7 102.5(3) . . ?
C1 C2 C3 115.9(4) . . ?
C7 C2 C3 114.1(4) . . ?
C2 C3 C4 111.1(4) . . ?
C5 C4 C3 112.9(4) . . ?
C6 C5 C4 124.2(4) . . ?
C5 C6 C7 124.9(4) . . ?
C6 C7 C2 110.3(3) . . ?
C6 C7 C8 111.2(3) . . ?
C2 C7 C8 104.9(3) . . ?
O2 C8 C7 109.7(3) . . ?
O2 C8 C12 103.3(3) . . ?
C7 C8 C12 106.8(3) . . ?
O3 C9 O2 104.0(3) . . ?
O3 C9 C11 108.9(3) . . ?
O2 C9 C11 109.1(3) . . ?
O3 C9 C10 110.3(3) . . ?
O2 C9 C10 111.2(3) . . ?
C11 C9 C10 112.9(4) . . ?
O3 C12 C1 106.7(3) . . ?
O3 C12 C8 105.3(3) . . ?
C1 C12 C8 104.6(3) . . ?
O4 C13 C14 126.6(4) . . ?
O4 C13 C24 125.0(4) . . ?
C14 C13 C24 108.3(3) . . ?
C15 C14 C13 113.8(3) . . ?
C15 C14 C19 114.4(4) . . ?
C13 C14 C19 102.3(3) . . ?
C14 C15 C16 111.6(4) . . ?
C17 C16 C15 111.8(4) . . ?
C18 C17 C16 125.1(5) . . ?
C17 C18 C19 124.2(5) . . ?
C18 C19 C20 111.3(4) . . ?
C18 C19 C14 110.7(3) . . ?
C20 C19 C14 104.7(3) . . ?
O5 C20 C19 109.7(3) . . ?
O5 C20 C24 102.9(3) . . ?
C19 C20 C24 106.8(3) . . ?
O5 C21 O6 104.6(3) . . ?
O5 C21 C22 109.2(3) . . ?
O6 C21 C22 107.4(3) . . ?
O5 C21 C23 111.8(4) . . ?
O6 C21 C23 111.0(3) . . ?
C22 C21 C23 112.4(3) . . ?
O6 C24 C13 107.3(3) . . ?
O6 C24 C20 105.3(3) . . ?
C13 C24 C20 104.8(3) . . ?
C21' O5' C20' 108.4(3) . . ?
C24' O6' C21' 108.4(3) . . ?
O4' C13' C24' 124.1(4) . . ?
O4' C13' C14' 126.6(4) . . ?
C24' C13' C14' 109.4(3) . . ?
C13' C14' C15' 115.5(4) . . ?
C13' C14' C19' 102.7(3) . . ?
C15' C14' C19' 113.6(4) . . ?
C14' C15' C16' 111.2(4) . . ?
C17' C16' C15' 112.3(4) . . ?
C18' C17' C16' 124.3(5) . . ?
C17' C18' C19' 124.5(5) . . ?
C18' C19' C14' 110.5(4) . . ?
C18' C19' C20' 111.5(4) . . ?
C14' C19' C20' 103.5(3) . . ?
O5' C20' C19' 110.7(4) . . ?
O5' C20' C24' 103.0(3) . . ?
C19' C20' C24' 106.8(3) . . ?
O5' C21' O6' 103.5(3) . . ?
O5' C21' C22' 109.6(4) . . ?
O6' C21' C22' 108.7(4) . . ?
O5' C21' C23' 111.6(4) . . ?
O6' C21' C23' 110.2(4) . . ?
C22' C21' C23' 112.8(4) . . ?
O6' C24' C13' 107.3(3) . . ?
O6' C24' C20' 105.3(3) . . ?
C13' C24' C20' 104.2(3) . . ?
C9' O2' C8' 107.2(3) . . ?
C9' O3' C12' 107.5(3) . . ?
O1' C1' C12' 124.4(4) . . ?
O1' C1' C2' 126.6(4) . . ?
C12' C1' C2' 109.0(3) . . ?
C1' C2' C3' 115.3(3) . . ?
C1' C2' C7' 101.8(3) . . ?
C3' C2' C7' 114.1(3) . . ?
C2' C3' C4' 111.9(3) . . ?
C5' C4' C3' 112.9(4) . . ?
C6' C5' C4' 124.3(4) . . ?
C5' C6' C7' 124.2(4) . . ?
C6' C7' C2' 111.2(3) . . ?
C6' C7' C8' 112.0(3) . . ?
C2' C7' C8' 104.3(3) . . ?
O2' C8' C12' 104.9(3) . . ?
O2' C8' C7' 109.3(3) . . ?
C12' C8' C7' 107.2(3) . . ?
O2' C9' O3' 103.7(3) . . ?
O2' C9' C10' 111.0(3) . . ?
O3' C9' C10' 110.3(3) . . ?
O2' C9' C11' 108.7(3) . . ?
O3' C9' C11' 109.2(3) . . ?
C10' C9' C11' 113.5(3) . . ?
O3' C12' C1' 106.4(3) . . ?
O3' C12' C8' 104.5(3) . . ?
C1' C12' C8' 104.6(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.048

_database_code_depnum_ccdc_archive 'CCDC 727043'
#######################################################################
#
#                 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_WWHADE105

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H19.50 N5 O3.50'
_chemical_formula_weight         313.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   8.5282(9)
_cell_length_b                   10.7576(11)
_cell_length_c                   41.024(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3763.6(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1467
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.108
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1332
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4915
_exptl_absorpt_correction_T_max  0.6434
_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  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23027
_diffrn_reflns_av_R_equivalents  0.1413
_diffrn_reflns_av_sigmaI/netI    0.1805
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         25.25
_reflns_number_total             6796
_reflns_number_gt                4698
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS 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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(4)
_refine_ls_number_reflns         6796
_refine_ls_number_parameters     406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1920
_refine_ls_R_factor_gt           0.1647
_refine_ls_wR_factor_ref         0.3918
_refine_ls_wR_factor_gt          0.3716
_refine_ls_goodness_of_fit_ref   1.732
_refine_ls_restrained_S_all      1.732
_refine_ls_shift/su_max          0.005
_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
N1 N 0.1915(7) 1.0464(7) 0.05909(16) 0.0251(16) Uani 1 1 d . . .
N2 N 0.1535(8) 1.0658(9) 0.0070(2) 0.050(2) Uani 1 1 d . . .
N3 N 0.5741(8) 1.1352(7) 0.00871(18) 0.0293(16) Uani 1 1 d . . .
N4 N 0.4723(10) 1.0877(9) 0.0606(2) 0.045(2) Uani 1 1 d . . .
N5 N 0.4221(9) 1.1380(10) -0.03673(19) 0.052(3) Uani 1 1 d . . .
H5A H 0.5005 1.1562 -0.0490 0.062 Uiso 1 1 calc R . .
H5B H 0.3303 1.1292 -0.0451 0.062 Uiso 1 1 calc R . .
O1 O 0.0831(7) 0.7941(6) 0.19039(13) 0.0338(15) Uani 1 1 d . . .
H1A H 0.0818 0.8681 0.1952 0.051 Uiso 1 1 calc R . .
O2 O -0.0345(10) 1.0559(6) 0.16487(14) 0.0470(19) Uani 1 1 d . . .
H2A H -0.0046 1.0226 0.1817 0.071 Uiso 1 1 calc R . .
O3 O -0.0650(6) 1.1548(5) 0.10611(13) 0.0267(13) Uani 1 1 d . . .
H3A H -0.0680 1.1844 0.0877 0.040 Uiso 1 1 calc R . .
C1 C 0.1810(13) 0.7753(10) 0.1586(2) 0.040(2) Uani 1 1 d . . .
H1B H 0.2892 0.7511 0.1636 0.048 Uiso 1 1 calc R . .
C2 C 0.1022(13) 0.6817(8) 0.1378(2) 0.040(2) Uani 1 1 d . . .
H2B H -0.0049 0.7067 0.1332 0.048 Uiso 1 1 calc R . .
H2C H 0.1004 0.6014 0.1486 0.048 Uiso 1 1 calc R . .
C3 C 0.1959(15) 0.6753(8) 0.1071(2) 0.049(3) Uani 1 1 d . . .
H3B H 0.1652 0.6023 0.0947 0.059 Uiso 1 1 calc R . .
H3C H 0.3063 0.6677 0.1124 0.059 Uiso 1 1 calc R . .
C4 C 0.1692(14) 0.7959(10) 0.0855(3) 0.054(3) Uani 1 1 d . . .
H4B H 0.2330 0.7919 0.0660 0.064 Uiso 1 1 calc R . .
H4C H 0.0600 0.8020 0.0791 0.064 Uiso 1 1 calc R . .
C5 C 0.2171(11) 0.9119(8) 0.1066(2) 0.033(2) Uani 1 1 d . . .
H5A H 0.3318 0.9157 0.1058 0.040 Uiso 1 1 calc R . .
C6 C 0.1732(10) 0.9117(8) 0.14359(19) 0.0276(18) Uani 1 1 d . . .
H6A H 0.2427 0.9677 0.1557 0.033 Uiso 1 1 calc R . .
C7 C -0.0016(11) 0.9780(7) 0.1382(2) 0.031(2) Uani 1 1 d . . .
H7A H -0.0791 0.9108 0.1388 0.038 Uiso 1 1 calc R . .
C8 C -0.0072(10) 1.0314(7) 0.10454(19) 0.0251(18) Uani 1 1 d . . .
H8A H -0.0674 0.9794 0.0894 0.030 Uiso 1 1 calc R . .
C9 C 0.1589(13) 1.0407(10) 0.09533(18) 0.039(2) Uani 1 1 d . . .
H9A H 0.2118 1.1081 0.1071 0.047 Uiso 1 1 calc R . .
C10 C 0.0974(9) 1.0474(7) 0.03498(16) 0.0208(17) Uani 1 1 d . . .
H10 H -0.0095 1.0349 0.0380 0.025 Uiso 1 1 calc R . .
C11 C 0.3051(12) 1.0863(9) 0.0131(2) 0.036(2) Uani 1 1 d . . .
C12 C 0.4414(12) 1.1246(11) -0.0072(2) 0.050(3) Uani 1 1 d . . .
C13 C 0.5945(12) 1.1211(10) 0.0381(2) 0.045(3) Uani 1 1 d . . .
H13A H 0.6952 1.1327 0.0462 0.054 Uiso 1 1 calc R . .
C14 C 0.3392(10) 1.0733(7) 0.04694(17) 0.0220(17) Uani 1 1 d . . .
O1' O 0.2536(12) 1.1221(8) 0.2287(2) 0.072(3) Uani 1 1 d . . .
O2' O 0.1189(10) 0.8808(7) 0.26121(18) 0.059(2) Uani 1 1 d . . .
H2'A H 0.0880 0.9169 0.2448 0.088 Uiso 1 1 calc R . .
O3' O 0.1070(10) 0.8100(7) 0.32335(18) 0.058(2) Uani 1 1 d . . .
H3'A H 0.1157 0.7871 0.3423 0.087 Uiso 1 1 calc R . .
N1' N 0.3943(8) 0.9169(6) 0.36236(16) 0.0286(16) Uani 1 1 d . . .
N2' N 0.3496(9) 0.9178(9) 0.4177(2) 0.046(2) Uani 1 1 d . . .
N3' N 0.7789(8) 0.8609(7) 0.41882(16) 0.0276(16) Uani 1 1 d . . .
N4' N 0.6748(7) 0.8701(5) 0.36250(14) 0.0189(14) Uani 1 1 d . . .
N5' N 0.6344(10) 0.8937(7) 0.46505(18) 0.037(2) Uani 1 1 d . . .
H5'A H 0.5515 0.9166 0.4753 0.045 Uiso 1 1 calc R . .
H5'B H 0.7191 0.8777 0.4756 0.045 Uiso 1 1 calc R . .
C1' C 0.3454(12) 1.1356(10) 0.2545(2) 0.044(3) Uani 1 1 d . . .
H1'A H 0.4511 1.1445 0.2454 0.053 Uiso 1 1 calc R . .
C2' C 0.319(2) 1.2517(9) 0.2730(3) 0.073(4) Uani 1 1 d . . .
H2'C H 0.3467 1.3225 0.2596 0.087 Uiso 1 1 calc R . .
H2'D H 0.2090 1.2586 0.2786 0.087 Uiso 1 1 calc R . .
C3' C 0.4113(19) 1.2538(14) 0.3023(5) 0.094(6) Uani 1 1 d . . .
H3'B H 0.5202 1.2623 0.2959 0.113 Uiso 1 1 calc R . .
H3'C H 0.3835 1.3287 0.3141 0.113 Uiso 1 1 calc R . .
C4' C 0.4024(15) 1.1533(10) 0.3246(3) 0.058(4) Uani 1 1 d . . .
H4'A H 0.4819 1.1652 0.3412 0.070 Uiso 1 1 calc R . .
H4'B H 0.3011 1.1560 0.3353 0.070 Uiso 1 1 calc R . .
C5' C 0.4225(11) 1.0341(10) 0.3109(2) 0.040(2) Uani 1 1 d . . .
H5'C H 0.5358 1.0208 0.3089 0.048 Uiso 1 1 calc R . .
C6' C 0.3563(19) 1.0326(13) 0.2761(2) 0.072(4) Uani 1 1 d . . .
H6'A H 0.4137 0.9677 0.2644 0.086 Uiso 1 1 calc R . .
C7' C 0.3554(11) 0.9176(10) 0.3274(3) 0.049(3) Uani 1 1 d . . .
H7'A H 0.4025 0.8441 0.3173 0.059 Uiso 1 1 calc R . .
C8' C 0.1861(13) 0.9202(9) 0.3192(2) 0.040(3) Uani 1 1 d . . .
H8'A H 0.1368 0.9813 0.3337 0.048 Uiso 1 1 calc R . .
C9' C 0.1772(11) 0.9723(9) 0.2848(2) 0.035(2) Uani 1 1 d . . .
H9'A H 0.1025 1.0415 0.2852 0.042 Uiso 1 1 calc R . .
C10' C 0.2816(11) 0.9292(11) 0.3874(2) 0.044(3) Uani 1 1 d . . .
H10B H 0.1753 0.9432 0.3839 0.053 Uiso 1 1 calc R . .
C11' C 0.5056(9) 0.9053(7) 0.41235(17) 0.0209(17) Uani 1 1 d . . .
C12' C 0.6318(10) 0.8830(8) 0.4326(2) 0.036(2) Uani 1 1 d . . .
C13' C 0.7829(12) 0.8633(9) 0.3852(2) 0.037(2) Uani 1 1 d . . .
H13B H 0.8841 0.8592 0.3768 0.045 Uiso 1 1 calc R . .
C14' C 0.5384(11) 0.8918(7) 0.37766(18) 0.028(2) Uani 1 1 d . . .
O1W O 0.0444(15) 0.9928(11) 0.2162(3) 0.103(4) 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
N1 C10 1.274(10) . ?
N1 C14 1.385(11) . ?
N1 C9 1.514(10) . ?
N2 C10 1.261(12) . ?
N2 C11 1.335(13) . ?
N3 C13 1.226(11) . ?
N3 C12 1.311(12) . ?
N4 C14 1.276(12) . ?
N4 C13 1.440(13) . ?
N5 C12 1.233(12) . ?
O1 C1 1.560(11) . ?
O2 C7 1.408(10) . ?
O3 C8 1.417(10) . ?
C1 C2 1.482(13) . ?
C1 C6 1.593(14) . ?
C2 C3 1.495(13) . ?
C3 C4 1.586(13) . ?
C4 C5 1.573(16) . ?
C5 C9 1.543(12) . ?
C5 C6 1.561(11) . ?
C6 C7 1.667(11) . ?
C7 C8 1.495(12) . ?
C8 C9 1.470(14) . ?
C10 C11 2.029(12) . ?
C11 C14 1.427(11) . ?
C11 C12 1.487(13) . ?
O1' C1' 1.321(12) . ?
O2' C9' 1.468(13) . ?
O3' C8' 1.374(13) . ?
N1' C14' 1.406(11) . ?
N1' C10' 1.413(12) . ?
N1' C7' 1.471(14) . ?
N2' C11' 1.356(11) . ?
N2' C10' 1.377(11) . ?
N3' C13' 1.380(11) . ?
N3' C12' 1.396(12) . ?
N4' C13' 1.312(11) . ?
N4' C14' 1.339(11) . ?
N5' C12' 1.337(12) . ?
C1' C6' 1.423(15) . ?
C1' C2' 1.480(17) . ?
C2' C3' 1.43(2) . ?
C3' C4' 1.418(17) . ?
C4' C5' 1.411(16) . ?
C5' C6' 1.533(15) . ?
C5' C7' 1.536(13) . ?
C6' C9' 1.70(2) . ?
C7' C8' 1.483(14) . ?
C8' C9' 1.519(12) . ?
C11' C12' 1.380(12) . ?
C11' C14' 1.458(10) . ?

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
C10 N1 C14 106.9(6) . . ?
C10 N1 C9 130.3(7) . . ?
C14 N1 C9 121.9(7) . . ?
C10 N2 C11 102.8(8) . . ?
C13 N3 C12 126.9(8) . . ?
C14 N4 C13 113.0(8) . . ?
C2 C1 O1 109.0(8) . . ?
C2 C1 C6 112.6(7) . . ?
O1 C1 C6 100.5(7) . . ?
C1 C2 C3 106.0(8) . . ?
C2 C3 C4 110.9(8) . . ?
C5 C4 C3 107.8(8) . . ?
C9 C5 C6 102.5(6) . . ?
C9 C5 C4 117.6(8) . . ?
C6 C5 C4 118.1(7) . . ?
C5 C6 C1 111.6(6) . . ?
C5 C6 C7 94.8(6) . . ?
C1 C6 C7 118.9(7) . . ?
O2 C7 C8 118.9(7) . . ?
O2 C7 C6 109.2(7) . . ?
C8 C7 C6 108.5(6) . . ?
O3 C8 C9 106.4(7) . . ?
O3 C8 C7 109.2(6) . . ?
C9 C8 C7 103.4(7) . . ?
C8 C9 N1 115.6(7) . . ?
C8 C9 C5 99.9(8) . . ?
N1 C9 C5 105.8(7) . . ?
N2 C10 N1 118.1(7) . . ?
N2 C10 C11 39.9(5) . . ?
N1 C10 C11 78.2(5) . . ?
N2 C11 C14 111.4(9) . . ?
N2 C11 C12 134.3(9) . . ?
C14 C11 C12 114.3(9) . . ?
N2 C11 C10 37.3(5) . . ?
C14 C11 C10 74.1(5) . . ?
C12 C11 C10 170.7(8) . . ?
N5 C12 N3 126.4(9) . . ?
N5 C12 C11 118.5(9) . . ?
N3 C12 C11 115.0(8) . . ?
N3 C13 N4 124.0(8) . . ?
N4 C14 N1 132.5(7) . . ?
N4 C14 C11 126.7(8) . . ?
N1 C14 C11 100.7(7) . . ?
C14' N1' C10' 106.7(6) . . ?
C14' N1' C7' 129.3(7) . . ?
C10' N1' C7' 123.7(7) . . ?
C11' N2' C10' 106.0(8) . . ?
C13' N3' C12' 115.1(7) . . ?
C13' N4' C14' 106.9(6) . . ?
O1' C1' C6' 116.9(11) . . ?
O1' C1' C2' 114.5(9) . . ?
C6' C1' C2' 110.2(9) . . ?
C3' C2' C1' 111.2(11) . . ?
C4' C3' C2' 119.9(14) . . ?
C5' C4' C3' 115.4(12) . . ?
C4' C5' C6' 109.6(8) . . ?
C4' C5' C7' 121.3(9) . . ?
C6' C5' C7' 105.4(10) . . ?
C1' C6' C5' 126.6(12) . . ?
C1' C6' C9' 111.7(10) . . ?
C5' C6' C9' 98.0(8) . . ?
N1' C7' C8' 116.2(8) . . ?
N1' C7' C5' 110.6(9) . . ?
C8' C7' C5' 104.3(8) . . ?
O3' C8' C7' 115.7(8) . . ?
O3' C8' C9' 114.1(7) . . ?
C7' C8' C9' 105.5(9) . . ?
O2' C9' C8' 112.4(8) . . ?
O2' C9' C6' 115.0(7) . . ?
C8' C9' C6' 106.9(8) . . ?
N2' C10' N1' 111.2(8) . . ?
N2' C11' C12' 133.2(8) . . ?
N2' C11' C14' 110.9(7) . . ?
C12' C11' C14' 114.9(7) . . ?
N5' C12' C11' 126.7(9) . . ?
N5' C12' N3' 113.7(8) . . ?
C11' C12' N3' 119.1(8) . . ?
N4' C13' N3' 133.8(8) . . ?
N4' C14' N1' 125.8(7) . . ?
N4' C14' C11' 129.6(7) . . ?
N1' C14' C11' 104.4(7) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.752
_refine_diff_density_rms         0.141
# SQUEEZE RESULTS (APPEND TO CIF)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.056 0.750 0.000 616.3 298.2
2 0.045 0.250 0.500 615.8 298.1
_platon_squeeze_details          
;
;
_database_code_depnum_ccdc_archive 'CCDC 1000117'
