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

#######################################################################
#
#                 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
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#  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_tc_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H23 N3 O5'
_chemical_formula_sum            'C22 H23 N3 O5'
_chemical_formula_weight         409.44

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

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

_cell_length_a                   7.9078(8)
_cell_length_b                   10.8875(12)
_cell_length_c                   13.1152(14)
_cell_angle_alpha                72.008(2)
_cell_angle_beta                 78.518(2)
_cell_angle_gamma                80.023(2)
_cell_volume                     1044.87(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5674
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      29.09

_exptl_crystal_description       Block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   'Multi scan'
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   'SADABS; BRUKER, 2008'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16944
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         27.00
_reflns_number_total             4565
_reflns_number_gt                3358
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.3594P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4541
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1518
_refine_ls_wR_factor_gt          0.1321
_refine_ls_goodness_of_fit_ref   0.840
_refine_ls_restrained_S_all      0.840
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.24991(18) 0.02690(14) 0.43246(12) 0.0358(3) Uani 1 1 d . . .
C2 C 0.2333(2) 0.07429(15) 0.32411(12) 0.0414(4) Uani 1 1 d . . .
H2 H 0.2992 0.0317 0.2752 0.050 Uiso 1 1 calc R . .
C3 C 0.1180(2) 0.18626(15) 0.28633(12) 0.0407(4) Uani 1 1 d . . .
C4 C 0.0212(2) 0.24847(15) 0.36333(13) 0.0442(4) Uani 1 1 d . . .
H4 H -0.0569 0.3222 0.3411 0.053 Uiso 1 1 calc R . .
C5 C 0.0413(2) 0.20102(14) 0.47062(12) 0.0401(3) Uani 1 1 d . . .
H5 H -0.0241 0.2440 0.5194 0.048 Uiso 1 1 calc R . .
C6 C 0.15656(19) 0.09030(14) 0.50982(11) 0.0350(3) Uani 1 1 d . . .
C7 C 0.18694(19) 0.04433(14) 0.62011(12) 0.0378(3) Uani 1 1 d . . .
H7 H 0.2741 -0.0252 0.6341 0.045 Uiso 1 1 calc R . .
C8 C 0.1089(2) 0.08596(15) 0.70756(12) 0.0400(3) Uani 1 1 d . . .
C9 C 0.1708(2) 0.03529(18) 0.81205(13) 0.0507(4) Uani 1 1 d . . .
C10 C -0.0599(2) 0.18226(18) 0.81609(13) 0.0507(4) Uani 1 1 d . . .
C11 C -0.1964(3) 0.2611(2) 0.87167(17) 0.0780(7) Uani 1 1 d . . .
H11A H -0.1470 0.3300 0.8822 0.117 Uiso 1 1 calc R . .
H11B H -0.2439 0.2070 0.9408 0.117 Uiso 1 1 calc R . .
H11C H -0.2870 0.2976 0.8281 0.117 Uiso 1 1 calc R . .
C12 C -0.0027(3) 0.35800(19) 0.13679(14) 0.0620(5) Uani 1 1 d . . .
H12A H 0.0440 0.3945 0.0611 0.074 Uiso 1 1 calc R . .
H12B H 0.0104 0.4172 0.1760 0.074 Uiso 1 1 calc R . .
C13 C -0.1930(3) 0.3495(3) 0.14561(19) 0.0802(7) Uani 1 1 d . . .
H13A H -0.2073 0.2884 0.1095 0.120 Uiso 1 1 calc R . .
H13B H -0.2503 0.4336 0.1122 0.120 Uiso 1 1 calc R . .
H13C H -0.2430 0.3212 0.2207 0.120 Uiso 1 1 calc R . .
C14 C 0.1816(3) 0.1639(2) 0.09931(15) 0.0683(6) Uani 1 1 d . . .
H14A H 0.1055 0.1788 0.0460 0.082 Uiso 1 1 calc R . .
H14B H 0.1953 0.0713 0.1358 0.082 Uiso 1 1 calc R . .
C15 C 0.3540(4) 0.2035(4) 0.0422(2) 0.1183(13) Uani 1 1 d . . .
H15A H 0.3408 0.2939 0.0023 0.177 Uiso 1 1 calc R . .
H15B H 0.4026 0.1524 -0.0070 0.177 Uiso 1 1 calc R . .
H15C H 0.4301 0.1898 0.0943 0.177 Uiso 1 1 calc R . .
C16 C 0.4318(2) -0.16271(14) 0.40335(12) 0.0392(3) Uani 1 1 d . . .
H16A H 0.5056 -0.1148 0.3405 0.047 Uiso 1 1 calc R . .
H16B H 0.3406 -0.1899 0.3785 0.047 Uiso 1 1 calc R . .
C17 C 0.53738(19) -0.28004(14) 0.46742(13) 0.0390(3) Uani 1 1 d . . .
C18 C 0.6550(2) -0.36688(15) 0.42100(14) 0.0430(4) Uani 1 1 d . . .
C19 C 0.7543(2) -0.47169(17) 0.48168(17) 0.0555(5) Uani 1 1 d . . .
H19 H 0.8330 -0.5262 0.4476 0.067 Uiso 1 1 calc R . .
C20 C 0.7362(3) -0.49458(18) 0.59132(17) 0.0597(5) Uani 1 1 d . . .
H20 H 0.8009 -0.5654 0.6326 0.072 Uiso 1 1 calc R . .
C21 C 0.6210(3) -0.41161(18) 0.64035(16) 0.0579(5) Uani 1 1 d . . .
H21 H 0.6079 -0.4266 0.7151 0.070 Uiso 1 1 calc R . .
C22 C 0.5244(2) -0.30591(16) 0.57908(14) 0.0482(4) Uani 1 1 d . . .
H22 H 0.4486 -0.2506 0.6138 0.058 Uiso 1 1 calc R . .
N1 N -0.03683(18) 0.17889(14) 0.71761(10) 0.0458(3) Uani 1 1 d . . .
N2 N 0.6792(2) -0.35136(14) 0.30413(12) 0.0534(4) Uani 1 1 d . . .
N3 N 0.0992(2) 0.23313(14) 0.17889(11) 0.0541(4) Uani 1 1 d . . .
O1 O 0.2895(2) -0.04178(16) 0.84433(11) 0.0783(5) Uani 1 1 d . . .
O2 O 0.05677(17) 0.10146(13) 0.87957(9) 0.0583(3) Uani 1 1 d . . .
O3 O 0.35787(14) -0.08262(11) 0.47274(9) 0.0446(3) Uani 1 1 d . . .
O4 O 0.8078(2) -0.40894(17) 0.26329(14) 0.0903(5) Uani 1 1 d . . .
O5 O 0.5702(2) -0.28199(16) 0.25171(11) 0.0771(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0367(7) 0.0330(7) 0.0372(7) -0.0116(6) -0.0063(6) 0.0008(6)
C2 0.0466(8) 0.0406(8) 0.0355(7) -0.0154(6) -0.0031(6) 0.0031(6)
C3 0.0480(9) 0.0383(8) 0.0332(7) -0.0091(6) -0.0063(6) -0.0005(6)
C4 0.0515(9) 0.0380(8) 0.0403(8) -0.0120(6) -0.0104(7) 0.0076(7)
C5 0.0454(8) 0.0379(8) 0.0376(8) -0.0167(6) -0.0056(6) 0.0032(6)
C6 0.0366(7) 0.0348(7) 0.0348(7) -0.0128(6) -0.0055(6) -0.0026(6)
C7 0.0399(8) 0.0365(7) 0.0375(8) -0.0108(6) -0.0093(6) -0.0018(6)
C8 0.0454(8) 0.0415(8) 0.0335(7) -0.0102(6) -0.0093(6) -0.0037(6)
C9 0.0577(10) 0.0555(10) 0.0379(8) -0.0114(7) -0.0133(7) -0.0012(8)
C10 0.0577(10) 0.0589(10) 0.0348(8) -0.0163(7) -0.0056(7) -0.0009(8)
C11 0.0834(15) 0.0975(17) 0.0482(11) -0.0330(11) -0.0032(10) 0.0167(13)
C12 0.0791(13) 0.0539(11) 0.0386(9) -0.0029(8) -0.0097(8) 0.0125(9)
C13 0.0802(15) 0.0904(17) 0.0656(13) -0.0222(12) -0.0231(11) 0.0151(13)
C14 0.0802(14) 0.0824(14) 0.0380(9) -0.0218(9) -0.0152(9) 0.0173(11)
C15 0.0807(17) 0.158(3) 0.0726(16) -0.0053(18) 0.0084(14) 0.0271(18)
C16 0.0392(8) 0.0375(8) 0.0408(8) -0.0160(6) -0.0042(6) 0.0024(6)
C17 0.0366(8) 0.0337(7) 0.0454(8) -0.0113(6) -0.0039(6) -0.0032(6)
C18 0.0424(8) 0.0352(8) 0.0510(9) -0.0150(6) -0.0043(7) -0.0019(6)
C19 0.0539(10) 0.0400(9) 0.0696(12) -0.0181(8) -0.0092(9) 0.0069(7)
C20 0.0610(11) 0.0425(9) 0.0681(12) -0.0070(8) -0.0189(9) 0.0082(8)
C21 0.0665(12) 0.0517(10) 0.0488(10) -0.0060(8) -0.0136(8) 0.0011(9)
C22 0.0509(9) 0.0442(9) 0.0445(9) -0.0124(7) -0.0039(7) 0.0031(7)
N1 0.0498(8) 0.0524(8) 0.0349(7) -0.0167(6) -0.0070(6) 0.0029(6)
N2 0.0616(9) 0.0433(8) 0.0557(9) -0.0240(7) -0.0011(7) 0.0020(7)
N3 0.0705(10) 0.0506(8) 0.0334(7) -0.0101(6) -0.0097(6) 0.0118(7)
O1 0.0848(10) 0.0891(11) 0.0548(8) -0.0165(7) -0.0333(7) 0.0244(8)
O2 0.0696(8) 0.0728(8) 0.0324(6) -0.0172(5) -0.0123(5) 0.0015(7)
O3 0.0506(6) 0.0417(6) 0.0411(6) -0.0175(5) -0.0121(5) 0.0121(5)
O4 0.0965(12) 0.0870(11) 0.0771(10) -0.0429(9) 0.0052(9) 0.0305(9)
O5 0.0914(11) 0.0839(10) 0.0535(8) -0.0307(7) -0.0179(7) 0.0245(9)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O3 1.3665(17) . ?
C1 C2 1.379(2) . ?
C1 C6 1.417(2) . ?
C2 C3 1.409(2) . ?
C3 N3 1.372(2) . ?
C3 C4 1.414(2) . ?
C4 C5 1.373(2) . ?
C5 C6 1.404(2) . ?
C6 C7 1.432(2) . ?
C7 C8 1.358(2) . ?
C8 N1 1.410(2) . ?
C8 C9 1.459(2) . ?
C9 O1 1.196(2) . ?
C9 O2 1.403(2) . ?
C10 N1 1.279(2) . ?
C10 O2 1.375(2) . ?
C10 C11 1.479(3) . ?
C12 N3 1.462(2) . ?
C12 C13 1.503(3) . ?
C14 N3 1.459(2) . ?
C14 C15 1.484(4) . ?
C16 O3 1.4255(18) . ?
C16 C17 1.510(2) . ?
C17 C22 1.389(2) . ?
C17 C18 1.398(2) . ?
C18 C19 1.389(2) . ?
C18 N2 1.466(2) . ?
C19 C20 1.364(3) . ?
C20 C21 1.378(3) . ?
C21 C22 1.386(2) . ?
N2 O5 1.215(2) . ?
N2 O4 1.218(2) . ?

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
O3 C1 C2 122.86(13) . . ?
O3 C1 C6 115.34(12) . . ?
C2 C1 C6 121.79(13) . . ?
C1 C2 C3 121.00(14) . . ?
N3 C3 C2 121.36(14) . . ?
N3 C3 C4 121.00(14) . . ?
C2 C3 C4 117.63(13) . . ?
C5 C4 C3 120.56(14) . . ?
C4 C5 C6 122.74(14) . . ?
C5 C6 C1 116.24(13) . . ?
C5 C6 C7 123.38(13) . . ?
C1 C6 C7 120.34(13) . . ?
C8 C7 C6 130.34(14) . . ?
C7 C8 N1 129.58(14) . . ?
C7 C8 C9 122.24(15) . . ?
N1 C8 C9 108.18(14) . . ?
O1 C9 O2 121.40(15) . . ?
O1 C9 C8 133.98(17) . . ?
O2 C9 C8 104.60(14) . . ?
N1 C10 O2 116.12(15) . . ?
N1 C10 C11 128.69(17) . . ?
O2 C10 C11 115.19(15) . . ?
N3 C12 C13 113.98(18) . . ?
N3 C14 C15 113.7(2) . . ?
O3 C16 C17 107.88(12) . . ?
C22 C17 C18 115.64(14) . . ?
C22 C17 C16 120.40(14) . . ?
C18 C17 C16 123.94(14) . . ?
C19 C18 C17 122.61(16) . . ?
C19 C18 N2 116.37(15) . . ?
C17 C18 N2 121.02(14) . . ?
C20 C19 C18 119.91(17) . . ?
C19 C20 C21 119.29(16) . . ?
C20 C21 C22 120.50(18) . . ?
C21 C22 C17 122.04(16) . . ?
C10 N1 C8 105.50(14) . . ?
O5 N2 O4 122.46(17) . . ?
O5 N2 C18 118.86(14) . . ?
O4 N2 C18 118.68(16) . . ?
C3 N3 C14 122.60(14) . . ?
C3 N3 C12 121.55(14) . . ?
C14 N3 C12 115.84(14) . . ?
C10 O2 C9 105.59(12) . . ?
C1 O3 C16 117.79(11) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 923721'
#######################################################################
#
#                 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_tc

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 N2 O3'
_chemical_formula_sum            'C15 H18 N2 O3'
_chemical_formula_weight         274.31

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

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

_cell_length_a                   12.521(2)
_cell_length_b                   15.687(3)
_cell_length_c                   14.616(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.589(4)
_cell_angle_gamma                90.00
_cell_volume                     2822.0(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2768
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      20.06

_exptl_crystal_description       Block
_exptl_crystal_colour            yellowish-green
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.0413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   'Multi scan'
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   'SADABS; BRUKER, 2008'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34391
_diffrn_reflns_av_R_equivalents  0.0904
_diffrn_reflns_av_sigmaI/netI    0.0698
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         27.00
_reflns_number_total             5653
_reflns_number_gt                2508
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0721P)^2^+0.9919P] 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         5653
_refine_ls_number_parameters     375
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1591
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1941
_refine_ls_wR_factor_gt          0.1454
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2717(3) 1.0255(2) 0.7266(2) 0.0464(8) Uani 1 1 d . . .
C2 C 0.1985(3) 0.96700(19) 0.75925(19) 0.0436(8) Uani 1 1 d . . .
C3 C 0.1284(3) 0.9198(2) 0.6982(2) 0.0482(8) Uani 1 1 d . . .
H3 H 0.0825 0.8813 0.7200 0.058 Uiso 1 1 calc R . .
C4 C 0.1245(2) 0.92877(19) 0.60084(19) 0.0441(8) Uani 1 1 d . . .
C5 C 0.0539(3) 0.8837(2) 0.5319(2) 0.0520(9) Uani 1 1 d . . .
H5 H 0.0063 0.8442 0.5499 0.062 Uiso 1 1 calc R . .
C6 C 0.0528(3) 0.8959(2) 0.4394(2) 0.0535(9) Uani 1 1 d . . .
H6 H 0.0068 0.8631 0.3960 0.064 Uiso 1 1 calc R . .
C7 C 0.1204(3) 0.9575(2) 0.4083(2) 0.0505(8) Uani 1 1 d . . .
C8 C 0.1912(3) 1.0033(2) 0.4766(2) 0.0513(8) Uani 1 1 d . . .
H8 H 0.2372 1.0444 0.4593 0.062 Uiso 1 1 calc R . .
C9 C 0.1921(2) 0.98711(19) 0.5689(2) 0.0440(8) Uani 1 1 d . . .
C10 C 0.1515(3) 0.9210(2) 0.9085(2) 0.0571(9) Uani 1 1 d . . .
C11 C 0.1798(3) 0.9329(2) 1.0116(2) 0.0688(11) Uani 1 1 d . . .
H11A H 0.1235 0.9649 1.0324 0.103 Uiso 1 1 calc R . .
H11B H 0.2474 0.9631 1.0270 0.103 Uiso 1 1 calc R . .
H11C H 0.1868 0.8782 1.0416 0.103 Uiso 1 1 calc R . .
C12 C 0.0542(3) 0.9178(2) 0.2442(2) 0.0641(10) Uani 1 1 d . . .
H12A H 0.0438 0.9471 0.1848 0.077 Uiso 1 1 calc R . .
H12B H -0.0171 0.9065 0.2586 0.077 Uiso 1 1 calc R . .
C13 C 0.1101(3) 0.8342(3) 0.2350(3) 0.0831(12) Uani 1 1 d . . .
H13A H 0.1813 0.8447 0.2219 0.125 Uiso 1 1 calc R . .
H13B H 0.0684 0.8018 0.1852 0.125 Uiso 1 1 calc R . .
H13C H 0.1162 0.8028 0.2921 0.125 Uiso 1 1 calc R . .
C14 C 0.1647(4) 1.0511(3) 0.2820(3) 0.0901(14) Uani 1 1 d . . .
H14A H 0.1211 1.0707 0.2240 0.108 Uiso 1 1 calc R . .
H14B H 0.1676 1.0965 0.3275 0.108 Uiso 1 1 calc R . .
C15 C 0.2725(4) 1.0319(4) 0.2680(3) 0.124(2) Uani 1 1 d . . .
H15A H 0.3155 1.0123 0.3254 0.186 Uiso 1 1 calc R . .
H15B H 0.3049 1.0822 0.2476 0.186 Uiso 1 1 calc R . .
H15C H 0.2693 0.9882 0.2216 0.186 Uiso 1 1 calc R . .
C16 C 0.4675(3) 0.1019(2) 0.0388(2) 0.0492(8) Uani 1 1 d . . .
C17 C 0.5407(3) 0.15633(19) 0.0000(2) 0.0450(8) Uani 1 1 d . . .
C18 C 0.6148(3) 0.2046(2) 0.0564(2) 0.0476(8) Uani 1 1 d . . .
H18 H 0.6612 0.2399 0.0308 0.057 Uiso 1 1 calc R . .
C19 C 0.6218(2) 0.20161(18) 0.1545(2) 0.0408(7) Uani 1 1 d . . .
C20 C 0.6933(3) 0.2507(2) 0.2183(2) 0.0500(8) Uani 1 1 d . . .
H20 H 0.7418 0.2868 0.1963 0.060 Uiso 1 1 calc R . .
C21 C 0.6943(3) 0.2474(2) 0.3118(2) 0.0526(9) Uani 1 1 d . . .
H21 H 0.7412 0.2827 0.3516 0.063 Uiso 1 1 calc R . .
C22 C 0.6253(3) 0.1909(2) 0.3490(2) 0.0515(8) Uani 1 1 d . . .
C23 C 0.5544(3) 0.1405(2) 0.2857(2) 0.0509(8) Uani 1 1 d . . .
H23 H 0.5078 0.1023 0.3073 0.061 Uiso 1 1 calc R . .
C24 C 0.5537(2) 0.14754(19) 0.1918(2) 0.0435(7) Uani 1 1 d . . .
C25 C 0.5794(3) 0.1978(2) -0.1538(2) 0.0565(9) Uani 1 1 d . . .
C26 C 0.5426(3) 0.1851(3) -0.2563(2) 0.0754(12) Uani 1 1 d . . .
H26A H 0.4910 0.2286 -0.2802 0.113 Uiso 1 1 calc R . .
H26B H 0.5092 0.1301 -0.2674 0.113 Uiso 1 1 calc R . .
H26C H 0.6040 0.1886 -0.2869 0.113 Uiso 1 1 calc R . .
C27 C 0.6981(3) 0.2400(3) 0.5089(2) 0.0773(12) Uani 1 1 d . . .
H27A H 0.7684 0.2437 0.4902 0.093 Uiso 1 1 calc R . .
H27B H 0.7090 0.2135 0.5699 0.093 Uiso 1 1 calc R . .
C28 C 0.6550(4) 0.3279(3) 0.5161(3) 0.1044(16) Uani 1 1 d . . .
H28A H 0.6445 0.3549 0.4561 0.157 Uiso 1 1 calc R . .
H28B H 0.7058 0.3605 0.5596 0.157 Uiso 1 1 calc R . .
H28C H 0.5868 0.3250 0.5372 0.157 Uiso 1 1 calc R . .
C29 C 0.5577(4) 0.1262(3) 0.4829(3) 0.0821(13) Uani 1 1 d . . .
H29A H 0.5931 0.1112 0.5455 0.098 Uiso 1 1 calc R . .
H29B H 0.5492 0.0744 0.4461 0.098 Uiso 1 1 calc R . .
C30 C 0.4480(4) 0.1619(3) 0.4862(3) 0.0977(15) Uani 1 1 d . . .
H30A H 0.4556 0.2132 0.5226 0.146 Uiso 1 1 calc R . .
H30B H 0.4066 0.1210 0.5139 0.146 Uiso 1 1 calc R . .
H30C H 0.4110 0.1745 0.4241 0.146 Uiso 1 1 calc R . .
H1 H 0.260(3) 1.000(2) 0.883(3) 0.072(13) Uiso 1 1 d . . .
H3A H 0.471(2) 0.1241(19) -0.118(2) 0.041(10) Uiso 1 1 d . . .
N1 N 0.2107(2) 0.96617(18) 0.85700(18) 0.0486(7) Uani 1 1 d . . .
N2 N 0.1131(3) 0.97388(19) 0.31544(18) 0.0677(9) Uani 1 1 d . . .
N3 N 0.5235(3) 0.1542(2) -0.09777(19) 0.0538(8) Uani 1 1 d . . .
N4 N 0.6276(2) 0.18567(19) 0.44313(18) 0.0658(8) Uani 1 1 d . . .
O1 O 0.3395(2) 1.06858(15) 0.77578(15) 0.0631(7) Uani 1 1 d . . .
O2 O 0.26501(17) 1.03456(13) 0.63258(13) 0.0520(6) Uani 1 1 d . . .
O3 O 0.0778(2) 0.87312(19) 0.87344(16) 0.0869(9) Uani 1 1 d . . .
O4 O 0.47834(17) 0.09840(14) 0.13363(13) 0.0528(6) Uani 1 1 d . . .
O5 O 0.39519(19) 0.05886(16) -0.00627(15) 0.0650(7) Uani 1 1 d . . .
O6 O 0.6555(2) 0.24420(18) -0.12271(16) 0.0796(8) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.049(2) 0.052(2) 0.0349(18) 0.0027(15) -0.0009(18) -0.0002(16)
C2 0.049(2) 0.051(2) 0.0309(16) 0.0012(14) 0.0080(16) 0.0058(16)
C3 0.051(2) 0.055(2) 0.0410(18) -0.0004(15) 0.0148(17) -0.0038(16)
C4 0.0496(19) 0.0454(19) 0.0376(17) 0.0035(14) 0.0087(17) -0.0016(15)
C5 0.058(2) 0.054(2) 0.0445(19) -0.0002(15) 0.0108(18) -0.0167(17)
C6 0.059(2) 0.061(2) 0.0398(18) -0.0092(15) 0.0073(18) -0.0156(17)
C7 0.057(2) 0.058(2) 0.0359(18) -0.0011(15) 0.0076(17) -0.0085(17)
C8 0.057(2) 0.059(2) 0.0384(18) 0.0003(15) 0.0100(18) -0.0152(16)
C9 0.0456(19) 0.048(2) 0.0368(17) -0.0035(14) 0.0018(16) -0.0070(15)
C10 0.061(2) 0.070(3) 0.0407(19) 0.0046(17) 0.011(2) 0.0004(19)
C11 0.081(3) 0.088(3) 0.0394(19) 0.0031(18) 0.017(2) -0.001(2)
C12 0.076(3) 0.080(3) 0.0349(18) -0.0063(17) 0.0072(19) -0.014(2)
C13 0.084(3) 0.097(3) 0.070(3) -0.015(2) 0.018(2) -0.008(2)
C14 0.088(3) 0.130(4) 0.047(2) -0.003(2) -0.003(3) -0.010(3)
C15 0.087(4) 0.207(6) 0.076(3) -0.026(3) 0.012(3) -0.030(4)
C16 0.052(2) 0.058(2) 0.0363(18) -0.0047(15) 0.0051(18) 0.0020(17)
C17 0.051(2) 0.050(2) 0.0339(17) 0.0011(14) 0.0055(17) 0.0061(16)
C18 0.053(2) 0.051(2) 0.0397(18) 0.0027(15) 0.0100(17) 0.0024(16)
C19 0.0434(18) 0.0394(18) 0.0398(17) -0.0010(14) 0.0086(16) 0.0033(14)
C20 0.054(2) 0.052(2) 0.0440(19) -0.0037(15) 0.0079(18) -0.0050(16)
C21 0.052(2) 0.061(2) 0.0447(19) -0.0095(16) 0.0073(18) -0.0076(17)
C22 0.055(2) 0.060(2) 0.0387(18) -0.0052(15) 0.0055(18) 0.0031(17)
C23 0.054(2) 0.057(2) 0.0426(19) -0.0058(15) 0.0124(18) -0.0077(17)
C24 0.0445(19) 0.0477(19) 0.0370(17) -0.0068(14) 0.0038(16) -0.0002(15)
C25 0.060(2) 0.070(3) 0.0389(19) 0.0023(17) 0.008(2) 0.0037(19)
C26 0.081(3) 0.103(3) 0.043(2) 0.0037(19) 0.012(2) 0.000(2)
C27 0.081(3) 0.104(3) 0.046(2) -0.009(2) 0.010(2) -0.010(2)
C28 0.102(4) 0.106(4) 0.115(4) -0.041(3) 0.044(3) -0.025(3)
C29 0.104(4) 0.095(3) 0.048(2) -0.006(2) 0.016(2) -0.015(3)
C30 0.105(4) 0.118(4) 0.072(3) -0.010(3) 0.022(3) -0.031(3)
N1 0.0555(19) 0.0577(19) 0.0329(15) 0.0021(13) 0.0090(15) -0.0021(15)
N2 0.091(2) 0.075(2) 0.0364(16) -0.0009(14) 0.0118(17) -0.0359(18)
N3 0.059(2) 0.065(2) 0.0366(16) -0.0034(14) 0.0070(16) -0.0081(17)
N4 0.077(2) 0.081(2) 0.0385(16) -0.0080(15) 0.0095(16) -0.0200(17)
O1 0.0706(16) 0.0719(17) 0.0419(13) -0.0046(11) -0.0026(13) -0.0200(13)
O2 0.0565(14) 0.0610(15) 0.0365(12) -0.0009(10) 0.0031(11) -0.0147(11)
O3 0.093(2) 0.123(3) 0.0455(15) 0.0032(15) 0.0142(16) -0.0421(19)
O4 0.0587(15) 0.0626(15) 0.0370(12) -0.0056(10) 0.0087(12) -0.0154(11)
O5 0.0616(15) 0.0851(19) 0.0465(14) -0.0109(12) 0.0054(13) -0.0204(14)
O6 0.087(2) 0.101(2) 0.0515(16) 0.0036(14) 0.0133(16) -0.0252(17)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.212(3) . ?
C1 O2 1.369(3) . ?
C1 C2 1.439(4) . ?
C2 C3 1.351(4) . ?
C2 N1 1.409(4) . ?
C3 C4 1.421(4) . ?
C4 C9 1.384(4) . ?
C4 C5 1.403(4) . ?
C5 C6 1.363(4) . ?
C6 C7 1.413(4) . ?
C7 N2 1.367(4) . ?
C7 C8 1.406(4) . ?
C8 C9 1.371(4) . ?
C9 O2 1.393(3) . ?
C10 O3 1.226(4) . ?
C10 N1 1.350(4) . ?
C10 C11 1.496(4) . ?
C12 N2 1.456(4) . ?
C12 C13 1.504(5) . ?
C14 C15 1.435(6) . ?
C14 N2 1.496(5) . ?
C16 O5 1.221(4) . ?
C16 O4 1.369(3) . ?
C16 C17 1.442(4) . ?
C17 C18 1.354(4) . ?
C17 N3 1.405(4) . ?
C18 C19 1.421(4) . ?
C19 C24 1.384(4) . ?
C19 C20 1.399(4) . ?
C20 C21 1.365(4) . ?
C21 C22 1.414(4) . ?
C22 N4 1.373(4) . ?
C22 C23 1.403(4) . ?
C23 C24 1.377(4) . ?
C24 O4 1.383(3) . ?
C25 O6 1.220(4) . ?
C25 N3 1.356(4) . ?
C25 C26 1.497(4) . ?
C27 N4 1.455(4) . ?
C27 C28 1.493(6) . ?
C29 N4 1.470(4) . ?
C29 C30 1.492(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 116.4(3) . . ?
O1 C1 C2 125.3(3) . . ?
O2 C1 C2 118.3(3) . . ?
C3 C2 N1 127.0(3) . . ?
C3 C2 C1 120.4(3) . . ?
N1 C2 C1 112.6(3) . . ?
C2 C3 C4 120.4(3) . . ?
C9 C4 C5 115.8(3) . . ?
C9 C4 C3 119.4(3) . . ?
C5 C4 C3 124.8(3) . . ?
C6 C5 C4 122.1(3) . . ?
C5 C6 C7 121.2(3) . . ?
N2 C7 C8 121.8(3) . . ?
N2 C7 C6 120.9(3) . . ?
C8 C7 C6 117.2(3) . . ?
C9 C8 C7 119.7(3) . . ?
C8 C9 C4 124.0(3) . . ?
C8 C9 O2 116.4(3) . . ?
C4 C9 O2 119.6(2) . . ?
O3 C10 N1 122.5(3) . . ?
O3 C10 C11 121.2(3) . . ?
N1 C10 C11 116.3(3) . . ?
N2 C12 C13 114.1(3) . . ?
C15 C14 N2 110.5(4) . . ?
O5 C16 O4 116.7(3) . . ?
O5 C16 C17 125.3(3) . . ?
O4 C16 C17 118.0(3) . . ?
C18 C17 N3 126.3(3) . . ?
C18 C17 C16 120.4(3) . . ?
N3 C17 C16 113.3(3) . . ?
C17 C18 C19 120.3(3) . . ?
C24 C19 C20 116.1(3) . . ?
C24 C19 C18 119.3(3) . . ?
C20 C19 C18 124.6(3) . . ?
C21 C20 C19 122.3(3) . . ?
C20 C21 C22 121.0(3) . . ?
N4 C22 C23 121.4(3) . . ?
N4 C22 C21 121.4(3) . . ?
C23 C22 C21 117.2(3) . . ?
C24 C23 C22 120.0(3) . . ?
C23 C24 O4 116.6(3) . . ?
C23 C24 C19 123.4(3) . . ?
O4 C24 C19 120.0(2) . . ?
O6 C25 N3 122.0(3) . . ?
O6 C25 C26 121.9(3) . . ?
N3 C25 C26 116.1(3) . . ?
N4 C27 C28 113.8(3) . . ?
N4 C29 C30 113.2(4) . . ?
C10 N1 C2 127.0(3) . . ?
C7 N2 C12 121.9(3) . . ?
C7 N2 C14 121.5(3) . . ?
C12 N2 C14 116.6(3) . . ?
C25 N3 C17 127.1(3) . . ?
C22 N4 C27 121.7(3) . . ?
C22 N4 C29 122.0(3) . . ?
C27 N4 C29 116.3(3) . . ?
C1 O2 C9 121.8(2) . . ?
C16 O4 C24 121.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 923722'