# Electronic Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012


#######################################################################
#
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#                                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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#  data retrieval see:
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data_6
_database_code_depnum_ccdc_archive 'CCDC 896906'
#TrackingRef 'Sleem_Combined_CIF.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H22 N2 O4, H2 O'
_chemical_formula_sum            'C16 H24 N2 O5'
_chemical_formula_weight         324.38

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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                   11.336(3)
_cell_length_b                   10.813(3)
_cell_length_c                   16.926(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 129.643(6)
_cell_angle_gamma                90.00
_cell_volume                     1597.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    7320
_cell_measurement_theta_min      2.3332
_cell_measurement_theta_max      30.5237

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.33
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_max  0.9796
_exptl_absorpt_correction_T_min  0.9642
_exptl_absorpt_process_details   '(T. Higashi, 2000)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'graphite - Rigaku SHINE'
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 14.63
_diffrn_reflns_number            21578
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0127
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3649
_reflns_number_gt                3601
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXL-97 (Acta Cryst. 2008. A64, 112-122)'
_computing_structure_refinement  'SHELXL-97 (Acta Cryst. 2008. A64, 112-122)'
_computing_molecular_graphics    'CrystalStructure3.7.0(Rigaku/MSC Inc.,2005)'
_computing_publication_material  'CrystalStructure3.7.0(Rigaku/MSC Inc.,2005)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

H1N, H2N, H1W and H2W were introduced in difference map positions, and
refined positionally with distance and angle restraints and with thermal
parameters fixed 1.2 times that of their bonding partner. All other
hydrogen atoms were introduced in calculated positions and refined on a
riding model.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0499P)^2^+0.5175P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3649
_refine_ls_number_parameters     221
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.065
_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 0.19461(10) 1.03950(7) 0.31389(6) 0.0322(2) Uani 1 1 d . . .
O2 O 0.37752(9) 0.74292(7) 0.59605(6) 0.02684(18) Uani 1 1 d . . .
O3 O 0.31355(10) 0.49139(7) 0.51905(6) 0.02740(18) Uani 1 1 d . . .
O4 O 0.18711(11) 0.41771(7) 0.18123(6) 0.0325(2) Uani 1 1 d . . .
O5 O 0.03448(12) 0.19019(9) 0.13684(7) 0.0402(2) Uani 1 1 d D . .
N1 N 0.20598(11) 0.89911(9) 0.41703(7) 0.0267(2) Uani 1 1 d D . .
N2 N 0.22638(11) 0.44812(8) 0.32903(7) 0.02365(19) Uani 1 1 d D . .
C1 C 0.17556(11) 0.70855(9) 0.28409(8) 0.0208(2) Uani 1 1 d . . .
H1 H 0.2277 0.6851 0.3533 0.025 Uiso 1 1 calc R . .
C2 C 0.14045(11) 0.61946(9) 0.21233(8) 0.0207(2) Uani 1 1 d . . .
C3 C 0.06247(12) 0.65458(10) 0.11068(8) 0.0230(2) Uani 1 1 d . . .
H3 H 0.0389 0.5945 0.0615 0.028 Uiso 1 1 calc R . .
C4 C 0.01913(12) 0.77667(10) 0.08091(8) 0.0245(2) Uani 1 1 d . . .
H4 H -0.0361 0.7997 0.0112 0.029 Uiso 1 1 calc R . .
C5 C 0.05641(12) 0.86510(10) 0.15284(8) 0.0228(2) Uani 1 1 d . . .
H5 H 0.0285 0.9490 0.1325 0.027 Uiso 1 1 calc R . .
C6 C 0.13474(11) 0.83187(9) 0.25500(8) 0.0204(2) Uani 1 1 d . . .
C7 C 0.17983(11) 0.93195(9) 0.33088(8) 0.0217(2) Uani 1 1 d . . .
C8 C 0.26927(14) 0.98425(10) 0.50228(9) 0.0287(2) Uani 1 1 d . . .
H8A H 0.2066 0.9805 0.5242 0.034 Uiso 1 1 calc R . .
H8B H 0.2631 1.0696 0.4788 0.034 Uiso 1 1 calc R . .
C9 C 0.43535(13) 0.95488(11) 0.59378(9) 0.0303(2) Uani 1 1 d . . .
H9A H 0.4911 0.9337 0.5685 0.036 Uiso 1 1 calc R . .
H9B H 0.4838 1.0297 0.6372 0.036 Uiso 1 1 calc R . .
C10 C 0.45146(13) 0.84955(11) 0.65856(8) 0.0296(2) Uani 1 1 d . . .
H10A H 0.5613 0.8317 0.7146 0.036 Uiso 1 1 calc R . .
H10B H 0.4045 0.8727 0.6897 0.036 Uiso 1 1 calc R . .
C11 C 0.38832(13) 0.63981(11) 0.65255(8) 0.0268(2) Uani 1 1 d . . .
H11A H 0.3654 0.6659 0.6975 0.032 Uiso 1 1 calc R . .
H11B H 0.4934 0.6055 0.6962 0.032 Uiso 1 1 calc R . .
C12 C 0.27528(13) 0.54316(11) 0.57805(8) 0.0270(2) Uani 1 1 d . . .
H12A H 0.2718 0.4762 0.6164 0.032 Uiso 1 1 calc R . .
H12B H 0.1720 0.5807 0.5310 0.032 Uiso 1 1 calc R . .
C13 C 0.38815(13) 0.37422(10) 0.55463(8) 0.0265(2) Uani 1 1 d . . .
H13A H 0.3213 0.3135 0.5530 0.032 Uiso 1 1 calc R . .
H13B H 0.4846 0.3815 0.6263 0.032 Uiso 1 1 calc R . .
C14 C 0.42253(12) 0.33082(10) 0.48585(8) 0.0248(2) Uani 1 1 d . . .
H14A H 0.4695 0.2476 0.5087 0.030 Uiso 1 1 calc R . .
H14B H 0.4990 0.3874 0.4949 0.030 Uiso 1 1 calc R . .
C15 C 0.28375(12) 0.32464(9) 0.37208(8) 0.0240(2) Uani 1 1 d . . .
H15A H 0.3125 0.2819 0.3348 0.029 Uiso 1 1 calc R . .
H15B H 0.2017 0.2761 0.3628 0.029 Uiso 1 1 calc R . .
C16 C 0.18641(12) 0.48612(9) 0.23978(8) 0.0222(2) Uani 1 1 d . . .
H1N H 0.1836(16) 0.8239(12) 0.4217(11) 0.032 Uiso 1 1 d D . .
H2N H 0.2159(16) 0.4970(12) 0.3651(10) 0.028 Uiso 1 1 d D . .
H1W H 0.0901(19) 0.2608(13) 0.1540(13) 0.048 Uiso 1 1 d D . .
H2W H 0.0917(19) 0.1436(14) 0.1956(12) 0.048 Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0460(5) 0.0186(4) 0.0293(4) 0.0007(3) 0.0228(4) -0.0034(3)
O2 0.0329(4) 0.0254(4) 0.0196(3) -0.0015(3) 0.0155(3) 0.0004(3)
O3 0.0388(4) 0.0235(4) 0.0261(4) 0.0035(3) 0.0236(4) 0.0070(3)
O4 0.0515(5) 0.0228(4) 0.0328(4) -0.0027(3) 0.0314(4) 0.0003(4)
O5 0.0519(6) 0.0297(5) 0.0228(4) -0.0008(3) 0.0164(4) -0.0076(4)
N1 0.0373(5) 0.0187(4) 0.0241(4) -0.0018(3) 0.0195(4) -0.0030(4)
N2 0.0312(5) 0.0178(4) 0.0228(4) 0.0003(3) 0.0176(4) 0.0040(3)
C1 0.0209(4) 0.0204(5) 0.0186(4) 0.0007(4) 0.0114(4) -0.0002(4)
C2 0.0203(4) 0.0207(5) 0.0224(5) -0.0007(4) 0.0142(4) -0.0016(4)
C3 0.0234(5) 0.0263(5) 0.0211(5) -0.0035(4) 0.0150(4) -0.0037(4)
C4 0.0236(5) 0.0294(5) 0.0192(5) 0.0026(4) 0.0131(4) -0.0007(4)
C5 0.0230(5) 0.0218(5) 0.0229(5) 0.0039(4) 0.0143(4) 0.0010(4)
C6 0.0187(4) 0.0205(5) 0.0204(5) 0.0000(4) 0.0116(4) -0.0009(4)
C7 0.0203(4) 0.0193(5) 0.0215(5) 0.0009(4) 0.0115(4) 0.0007(4)
C8 0.0385(6) 0.0223(5) 0.0268(5) -0.0033(4) 0.0215(5) 0.0012(4)
C9 0.0327(6) 0.0286(6) 0.0301(6) -0.0100(5) 0.0202(5) -0.0065(4)
C10 0.0290(5) 0.0321(6) 0.0215(5) -0.0059(4) 0.0132(4) 0.0020(4)
C11 0.0302(5) 0.0303(6) 0.0195(5) 0.0033(4) 0.0157(4) 0.0056(4)
C12 0.0314(5) 0.0294(5) 0.0254(5) 0.0016(4) 0.0206(5) 0.0039(4)
C13 0.0295(5) 0.0245(5) 0.0247(5) 0.0042(4) 0.0169(4) 0.0052(4)
C14 0.0249(5) 0.0223(5) 0.0258(5) 0.0017(4) 0.0155(4) 0.0036(4)
C15 0.0281(5) 0.0165(5) 0.0254(5) 0.0001(4) 0.0162(4) 0.0021(4)
C16 0.0238(5) 0.0203(5) 0.0235(5) -0.0027(4) 0.0156(4) -0.0023(4)

_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 C7 1.2349(13) . ?
O2 C10 1.4212(14) . ?
O2 C11 1.4224(14) . ?
O3 C13 1.4259(13) . ?
O3 C12 1.4323(13) . ?
O4 C16 1.2407(13) . ?
O5 H1W 0.912(14) . ?
O5 H2W 0.916(13) . ?
N1 C7 1.3373(14) . ?
N1 C8 1.4572(14) . ?
N1 H1N 0.870(12) . ?
N2 C16 1.3353(14) . ?
N2 C15 1.4601(13) . ?
N2 H2N 0.871(12) . ?
C1 C6 1.3942(14) . ?
C1 C2 1.3946(14) . ?
C1 H1 0.9500 . ?
C2 C3 1.3947(15) . ?
C2 C16 1.5024(15) . ?
C3 C4 1.3864(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3853(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.3958(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.4981(14) . ?
C8 C9 1.5243(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5091(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5041(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5187(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5239(15) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

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 O2 C11 112.24(9) . . ?
C13 O3 C12 114.49(8) . . ?
H1W O5 H2W 104.3(14) . . ?
C7 N1 C8 122.58(10) . . ?
C7 N1 H1N 118.2(10) . . ?
C8 N1 H1N 119.2(10) . . ?
C16 N2 C15 124.58(9) . . ?
C16 N2 H2N 120.4(9) . . ?
C15 N2 H2N 115.0(9) . . ?
C6 C1 C2 120.48(9) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C1 C2 C3 119.36(10) . . ?
C1 C2 C16 122.94(9) . . ?
C3 C2 C16 117.68(9) . . ?
C4 C3 C2 120.42(10) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 119.95(10) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.49(10) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.29(9) . . ?
C1 C6 C7 122.23(9) . . ?
C5 C6 C7 118.39(9) . . ?
O1 C7 N1 122.37(10) . . ?
O1 C7 C6 120.22(10) . . ?
N1 C7 C6 117.39(9) . . ?
N1 C8 C9 112.53(9) . . ?
N1 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 113.20(10) . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.8 . . ?
O2 C10 C9 109.32(9) . . ?
O2 C10 H10A 109.8 . . ?
C9 C10 H10A 109.8 . . ?
O2 C10 H10B 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
O2 C11 C12 108.61(9) . . ?
O2 C11 H11A 110.0 . . ?
C12 C11 H11A 110.0 . . ?
O2 C11 H11B 110.0 . . ?
C12 C11 H11B 110.0 . . ?
H11A C11 H11B 108.3 . . ?
O3 C12 C11 112.40(9) . . ?
O3 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
O3 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
O3 C13 C14 108.90(9) . . ?
O3 C13 H13A 109.9 . . ?
C14 C13 H13A 109.9 . . ?
O3 C13 H13B 109.9 . . ?
C14 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C13 C14 C15 114.79(9) . . ?
C13 C14 H14A 108.6 . . ?
C15 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
C15 C14 H14B 108.6 . . ?
H14A C14 H14B 107.5 . . ?
N2 C15 C14 111.26(8) . . ?
N2 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
N2 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
O4 C16 N2 123.35(10) . . ?
O4 C16 C2 120.19(9) . . ?
N2 C16 C2 116.46(9) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.039


data_7
_database_code_depnum_ccdc_archive 'CCDC 896907'
#TrackingRef 'Sleem_Combined_CIF.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H44 N4 O8'
_chemical_formula_sum            'C32 H44 N4 O8'
_chemical_formula_weight         612.72

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'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2

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

_cell_length_a                   5.0083(18)
_cell_length_b                   9.048(3)
_cell_length_c                   17.725(6)
_cell_angle_alpha                85.179(8)
_cell_angle_beta                 82.023(9)
_cell_angle_gamma                75.645(9)
_cell_volume                     769.6(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    163(2)
_cell_measurement_reflns_used    2705
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.6

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.323
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
Multiple attempts were made to grow X-ray diffraction single crystals,
however, the only successful collection, reported here, was performed
on a very tiny needle that diffracted poorly. The high data statistics
are the result of this weak data-set. Please note that this has also
resulted in large esd's on some bond lengths and angles.
;

_diffrn_ambient_temperature      163(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'graphite - Rigaku SHINE'
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 14.63
_diffrn_reflns_number            8677
_diffrn_reflns_av_R_equivalents  0.1457
_diffrn_reflns_av_sigmaI/netI    0.1657
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2656
_reflns_number_gt                1356
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_structure_solution    'SHELXL-97 (Acta Cryst.2008, A64, 112-122)'
_computing_structure_refinement  'SHELXL-97 (Acta Cryst.2008, A64, 112-122)'
_computing_molecular_graphics    'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0977P)^2^+1.0970P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2656
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2347
_refine_ls_R_factor_gt           0.1365
_refine_ls_wR_factor_ref         0.3084
_refine_ls_wR_factor_gt          0.2533
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_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 0.6767(10) 0.1600(5) 0.8423(3) 0.0491(14) Uani 1 1 d . . .
O2 O 1.0155(9) -0.4003(5) 0.8881(3) 0.0427(13) Uani 1 1 d . . .
O3 O 0.0031(9) 0.4320(5) 0.2719(3) 0.0427(13) Uani 1 1 d . . .
O4 O 0.7176(9) 0.2423(5) 0.5491(3) 0.0509(14) Uani 1 1 d . . .
N1 N 0.7336(12) -0.0917(6) 0.8745(3) 0.0429(17) Uani 1 1 d . . .
N2 N 0.2917(11) 0.2534(6) 0.5188(3) 0.0398(16) Uani 1 1 d . . .
C1 C 0.5635(12) 0.1081(7) 0.6940(4) 0.0335(16) Uani 1 1 d . . .
H1 H 0.6722 0.1805 0.6939 0.040 Uiso 1 1 calc R . .
C2 C 0.4419(12) 0.0994(7) 0.6304(4) 0.0320(16) Uani 1 1 d . . .
C3 C 0.2824(13) -0.0073(7) 0.6296(4) 0.0408(18) Uani 1 1 d . . .
H3 H 0.1975 -0.0138 0.5857 0.049 Uiso 1 1 calc R . .
C4 C 0.2496(13) -0.1031(7) 0.6935(4) 0.0377(17) Uani 1 1 d . . .
H4 H 0.1418 -0.1760 0.6938 0.045 Uiso 1 1 calc R . .
C5 C 0.3743(13) -0.0920(7) 0.7565(4) 0.0374(17) Uani 1 1 d . . .
H5 H 0.3519 -0.1589 0.7999 0.045 Uiso 1 1 calc R . .
C6 C 0.5309(13) 0.0131(7) 0.7589(4) 0.0356(17) Uani 1 1 d . . .
C7 C 0.6533(14) 0.0337(8) 0.8269(4) 0.0375(17) Uani 1 1 d . . .
C8 C 0.8633(14) -0.0788(7) 0.9390(4) 0.0394(17) Uani 1 1 d . . .
H8A H 0.7406 0.0019 0.9709 0.047 Uiso 1 1 calc R . .
H8B H 1.0387 -0.0475 0.9218 0.047 Uiso 1 1 calc R . .
C9 C 0.9258(15) -0.2278(7) 0.9870(4) 0.0409(18) Uani 1 1 d . . .
H9A H 0.9965 -0.2099 1.0341 0.049 Uiso 1 1 calc R . .
H9B H 0.7514 -0.2614 1.0023 0.049 Uiso 1 1 calc R . .
C10 C 1.1369(15) -0.3538(8) 0.9454(4) 0.0464(19) Uani 1 1 d . . .
H10A H 1.3014 -0.3162 0.9228 0.056 Uiso 1 1 calc R . .
H10B H 1.1982 -0.4413 0.9816 0.056 Uiso 1 1 calc R . .
C11 C 1.2031(14) -0.5116(7) 0.8413(4) 0.0435(19) Uani 1 1 d . . .
H11A H 1.2801 -0.6032 0.8732 0.052 Uiso 1 1 calc R . .
H11B H 1.3592 -0.4692 0.8161 0.052 Uiso 1 1 calc R . .
C12 C -0.0570(14) 0.5545(7) 0.2169(4) 0.0437(19) Uani 1 1 d . . .
H12A H 0.1177 0.5794 0.1925 0.052 Uiso 1 1 calc R . .
H12B H -0.1745 0.6462 0.2421 0.052 Uiso 1 1 calc R . .
C13 C 0.1474(15) 0.4628(7) 0.3293(4) 0.0419(18) Uani 1 1 d . . .
H13A H 0.0611 0.5665 0.3474 0.050 Uiso 1 1 calc R . .
H13B H 0.3427 0.4590 0.3084 0.050 Uiso 1 1 calc R . .
C14 C 0.1381(13) 0.3467(7) 0.3943(4) 0.0371(17) Uani 1 1 d . . .
H14A H -0.0553 0.3609 0.4193 0.044 Uiso 1 1 calc R . .
H14B H 0.1971 0.2432 0.3744 0.044 Uiso 1 1 calc R . .
C15 C 0.3207(13) 0.3589(7) 0.4518(3) 0.0354(17) Uani 1 1 d . . .
H15A H 0.5164 0.3356 0.4281 0.043 Uiso 1 1 calc R . .
H15B H 0.2726 0.4650 0.4685 0.043 Uiso 1 1 calc R . .
C16 C 0.4958(14) 0.2036(7) 0.5625(4) 0.0386(18) Uani 1 1 d . . .
H2A H 0.141(14) 0.238(7) 0.532(4) 0.045 Uiso 1 1 d . . .
H1A H 0.744(14) -0.173(8) 0.856(4) 0.050 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.057(3) 0.035(3) 0.057(3) -0.004(2) -0.018(3) -0.008(2)
O2 0.043(3) 0.031(3) 0.050(3) -0.011(2) -0.007(2) 0.002(2)
O3 0.048(3) 0.031(3) 0.049(3) 0.006(2) -0.009(2) -0.009(2)
O4 0.028(3) 0.053(3) 0.072(4) 0.010(3) -0.007(2) -0.013(2)
N1 0.057(4) 0.024(3) 0.047(4) 0.001(3) -0.011(3) -0.006(3)
N2 0.024(3) 0.044(4) 0.051(4) -0.002(3) -0.001(3) -0.008(3)
C1 0.022(3) 0.032(4) 0.048(4) -0.012(3) -0.001(3) -0.009(3)
C2 0.017(3) 0.028(4) 0.048(4) -0.006(3) -0.001(3) -0.001(3)
C3 0.035(4) 0.042(4) 0.042(4) -0.002(4) -0.004(3) -0.004(3)
C4 0.036(4) 0.033(4) 0.048(5) -0.007(3) -0.003(4) -0.016(3)
C5 0.031(4) 0.030(4) 0.047(4) -0.004(3) -0.006(3) 0.001(3)
C6 0.026(4) 0.031(4) 0.046(4) -0.003(3) 0.003(3) -0.002(3)
C7 0.040(4) 0.034(4) 0.041(4) -0.012(4) -0.002(3) -0.013(3)
C8 0.044(4) 0.036(4) 0.038(4) -0.007(3) -0.008(4) -0.007(3)
C9 0.064(5) 0.031(4) 0.032(4) -0.001(3) -0.010(4) -0.016(3)
C10 0.050(5) 0.038(4) 0.053(5) 0.008(4) -0.019(4) -0.010(4)
C11 0.040(4) 0.030(4) 0.054(5) -0.001(3) -0.006(4) 0.003(3)
C12 0.046(5) 0.025(4) 0.052(5) -0.006(4) 0.001(4) 0.004(3)
C13 0.053(5) 0.031(4) 0.044(4) -0.004(3) -0.017(4) -0.009(3)
C14 0.033(4) 0.038(4) 0.040(4) 0.003(3) -0.003(3) -0.012(3)
C15 0.033(4) 0.039(4) 0.035(4) 0.001(3) -0.001(3) -0.013(3)
C16 0.023(4) 0.036(4) 0.053(5) -0.002(4) -0.002(4) -0.002(3)

_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 C7 1.234(7) . ?
O2 C10 1.396(7) . ?
O2 C11 1.428(7) . ?
O3 C13 1.409(7) . ?
O3 C12 1.415(7) . ?
O4 C16 1.233(7) . ?
N1 C7 1.366(8) . ?
N1 C8 1.418(8) . ?
N1 H1A 0.81(7) . ?
N2 C16 1.335(9) . ?
N2 C15 1.473(8) . ?
N2 H2A 0.80(7) . ?
C1 C2 1.371(9) . ?
C1 C6 1.392(9) . ?
C1 H1 0.9500 . ?
C2 C3 1.399(9) . ?
C2 C16 1.501(9) . ?
C3 C4 1.384(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.471(9) . ?
C8 C9 1.521(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.513(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.473(9) 2_656 ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C11 1.473(9) 2_656 ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.497(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.488(8) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

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 O2 C11 113.7(5) . . ?
C13 O3 C12 113.3(5) . . ?
C7 N1 C8 119.8(6) . . ?
C7 N1 H1A 114(5) . . ?
C8 N1 H1A 123(5) . . ?
C16 N2 C15 121.3(6) . . ?
C16 N2 H2A 121(5) . . ?
C15 N2 H2A 117(5) . . ?
C2 C1 C6 121.4(6) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C1 C2 C3 119.9(6) . . ?
C1 C2 C16 117.5(6) . . ?
C3 C2 C16 122.6(6) . . ?
C4 C3 C2 119.3(7) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 119.5(6) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 122.3(7) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C1 117.6(7) . . ?
C5 C6 C7 123.5(6) . . ?
C1 C6 C7 118.9(6) . . ?
O1 C7 N1 120.4(6) . . ?
O1 C7 C6 121.8(6) . . ?
N1 C7 C6 117.7(6) . . ?
N1 C8 C9 112.2(6) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 112.9(5) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
O2 C10 C9 108.9(5) . . ?
O2 C10 H10A 109.9 . . ?
C9 C10 H10A 109.9 . . ?
O2 C10 H10B 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
O2 C11 C12 109.9(5) . 2_656 ?
O2 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 2_656 . ?
O2 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 2_656 . ?
H11A C11 H11B 108.2 . . ?
O3 C12 C11 109.6(6) . 2_656 ?
O3 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 2_656 . ?
O3 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 2_656 . ?
H12A C12 H12B 108.2 . . ?
O3 C13 C14 109.4(5) . . ?
O3 C13 H13A 109.8 . . ?
C14 C13 H13A 109.8 . . ?
O3 C13 H13B 109.8 . . ?
C14 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
C15 C14 C13 112.1(6) . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
N2 C15 C14 111.7(5) . . ?
N2 C15 H15A 109.3 . . ?
C14 C15 H15A 109.3 . . ?
N2 C15 H15B 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
O4 C16 N2 122.1(7) . . ?
O4 C16 C2 120.9(6) . . ?
N2 C16 C2 116.9(6) . . ?

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 -0.4(9) . . . . ?
C6 C1 C2 C16 -178.3(5) . . . . ?
C1 C2 C3 C4 0.0(9) . . . . ?
C16 C2 C3 C4 177.8(6) . . . . ?
C2 C3 C4 C5 -0.1(9) . . . . ?
C3 C4 C5 C6 0.6(9) . . . . ?
C4 C5 C6 C1 -0.9(9) . . . . ?
C4 C5 C6 C7 176.4(6) . . . . ?
C2 C1 C6 C5 0.8(9) . . . . ?
C2 C1 C6 C7 -176.6(5) . . . . ?
C8 N1 C7 O1 -4.7(10) . . . . ?
C8 N1 C7 C6 177.3(6) . . . . ?
C5 C6 C7 O1 -146.0(7) . . . . ?
C1 C6 C7 O1 31.3(9) . . . . ?
C5 C6 C7 N1 32.0(9) . . . . ?
C1 C6 C7 N1 -150.7(6) . . . . ?
C7 N1 C8 C9 177.4(6) . . . . ?
N1 C8 C9 C10 65.0(8) . . . . ?
C11 O2 C10 C9 175.6(5) . . . . ?
C8 C9 C10 O2 -70.6(7) . . . . ?
C10 O2 C11 C12 179.5(5) . . . 2_656 ?
C13 O3 C12 C11 179.1(5) . . . 2_656 ?
C12 O3 C13 C14 165.7(5) . . . . ?
O3 C13 C14 C15 171.7(5) . . . . ?
C16 N2 C15 C14 155.1(6) . . . . ?
C13 C14 C15 N2 175.0(5) . . . . ?
C15 N2 C16 O4 -0.3(10) . . . . ?
C15 N2 C16 C2 178.6(6) . . . . ?
C1 C2 C16 O4 31.5(9) . . . . ?
C3 C2 C16 O4 -146.3(6) . . . . ?
C1 C2 C16 N2 -147.4(6) . . . . ?
C3 C2 C16 N2 34.8(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.078