# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Lu, Tong-Bu'
_publ_contact_author_email       lutongbu@mail.sysu.edu.cn
loop_
_publ_author_name
'Jia-Mei Chen'
'Zi-Zhou Wang'
'Tong-Bu Lu'

# Attachment '- 1a.cif'

data_exp_881_110924_1_2
_database_code_depnum_ccdc_archive 'CCDC 866968'
#TrackingRef '- 1a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N3 O7'
_chemical_formula_weight         399.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Pn

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

_cell_length_a                   4.4592(5)
_cell_length_b                   15.3668(11)
_cell_length_c                   13.3336(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.602(8)
_cell_angle_gamma                90.00
_cell_volume                     913.61(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1386
_cell_measurement_theta_min      2.8732
_cell_measurement_theta_max      66.9913

_exptl_crystal_description       Needle
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7961
_exptl_absorpt_correction_T_max  0.9538
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 10.5058
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3818
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         65.07
_reflns_number_total             2228
_reflns_number_gt                2003
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond 3.1a'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.0327P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_number_reflns         2228
_refine_ls_number_parameters     276
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0787
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.023
_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
N3 N 1.1210(7) 0.55396(17) 0.7681(2) 0.0300(6) Uani 1 1 d . . .
O3 O 1.2838(5) 0.68183(14) 0.81919(17) 0.0346(5) Uani 1 1 d . . .
N2 N 0.9825(6) 0.40952(16) 0.73092(18) 0.0285(6) Uani 1 1 d . . .
C14 C 0.9585(7) 0.4948(2) 0.7151(2) 0.0273(6) Uani 1 1 d . . .
C9 C 0.7172(7) 0.28128(19) 0.6549(2) 0.0298(7) Uani 1 1 d . . .
H9 H 0.8132 0.2380 0.6947 0.036 Uiso 1 1 calc R . .
N1 N 0.7599(6) 0.51173(17) 0.6415(2) 0.0285(6) Uani 1 1 d . . .
O2 O 0.9193(5) 0.67728(14) 0.69971(17) 0.0383(6) Uani 1 1 d . . .
O1 O 0.2801(6) 0.14337(15) 0.49178(18) 0.0471(6) Uani 1 1 d . . .
C11 C 0.6445(7) 0.4322(2) 0.6078(2) 0.0290(7) Uani 1 1 d . . .
C10 C 0.7847(7) 0.36891(19) 0.6657(2) 0.0280(7) Uani 1 1 d . . .
C16 C 1.2742(10) 0.7758(2) 0.8173(3) 0.0430(8) Uani 1 1 d . . .
H16A H 1.3346 0.7966 0.7510 0.064 Uiso 1 1 calc R . .
H16B H 1.4117 0.7991 0.8685 0.064 Uiso 1 1 calc R . .
H16C H 1.0697 0.7956 0.8311 0.064 Uiso 1 1 calc R . .
C15 C 1.0921(8) 0.64246(19) 0.7564(2) 0.0308(7) Uani 1 1 d . . .
C13 C 0.3653(8) 0.32458(19) 0.5236(2) 0.0300(6) Uani 1 1 d . . .
H13 H 0.2219 0.3077 0.4741 0.036 Uiso 1 1 calc R . .
C7 C 0.4158(8) 0.1672(2) 0.5679(2) 0.0326(7) Uani 1 1 d . . .
C1 C 0.5037(7) 0.10131(19) 0.6454(2) 0.0344(7) Uani 1 1 d . . .
C6 C 0.4533(9) 0.1157(2) 0.7476(2) 0.0429(8) Uani 1 1 d . . .
H6 H 0.3600 0.1679 0.7692 0.051 Uiso 1 1 calc R . .
C8 C 0.5013(7) 0.2600(2) 0.5827(2) 0.0304(7) Uani 1 1 d . . .
C12 C 0.4316(7) 0.41138(18) 0.5345(2) 0.0293(7) Uani 1 1 d . . .
H12 H 0.3375 0.4548 0.4944 0.035 Uiso 1 1 calc R . .
C3 C 0.7345(11) -0.0359(2) 0.6850(3) 0.0607(12) Uani 1 1 d . . .
H3 H 0.8342 -0.0873 0.6639 0.073 Uiso 1 1 calc R . .
C5 C 0.5404(10) 0.0533(2) 0.8166(3) 0.0549(10) Uani 1 1 d . . .
H5 H 0.5027 0.0621 0.8858 0.066 Uiso 1 1 calc R . .
C2 C 0.6415(9) 0.0250(2) 0.6147(3) 0.0469(10) Uani 1 1 d . . .
H2 H 0.6721 0.0145 0.5453 0.056 Uiso 1 1 calc R . .
C4 C 0.6829(11) -0.0222(2) 0.7850(3) 0.0620(12) Uani 1 1 d . . .
H4 H 0.7449 -0.0644 0.8330 0.074 Uiso 1 1 calc R . .
H2A H 1.130(9) 0.380(2) 0.784(3) 0.031(9) Uiso 1 1 d . . .
H3A H 1.239(10) 0.533(2) 0.806(3) 0.037(11) Uiso 1 1 d . . .
H1A H 0.724(12) 0.562(3) 0.619(3) 0.060(13) Uiso 1 1 d . . .
O5 O 1.4954(5) 0.46164(13) 0.89989(17) 0.0353(5) Uani 1 1 d . . .
O4 O 1.3237(5) 0.32937(13) 0.85572(17) 0.0356(5) Uani 1 1 d . . .
O6 O 1.7413(5) 0.25250(13) 0.96029(16) 0.0355(5) Uani 1 1 d . . .
O7 O 1.8780(6) 0.37817(14) 1.03243(17) 0.0395(5) Uani 1 1 d . . .
C18 C 1.7279(7) 0.33766(19) 0.9739(2) 0.0281(7) Uani 1 1 d . . .
C17 C 1.4936(7) 0.3806(2) 0.9032(2) 0.0274(6) Uani 1 1 d . . .
C19 C 1.9615(8) 0.2064(2) 1.0198(3) 0.0421(8) Uani 1 1 d . . .
H19A H 2.1614 0.2164 0.9922 0.063 Uiso 1 1 calc R . .
H19B H 1.9166 0.1440 1.0186 0.063 Uiso 1 1 calc R . .
H19C H 1.9563 0.2275 1.0891 0.063 Uiso 1 1 calc R . .

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
N3 0.0311(15) 0.0276(12) 0.0310(14) 0.0003(12) -0.0069(12) -0.0016(12)
O3 0.0374(13) 0.0291(10) 0.0370(11) -0.0012(8) -0.0076(10) -0.0053(9)
N2 0.0284(14) 0.0285(13) 0.0286(14) -0.0001(11) -0.0054(11) -0.0027(11)
C14 0.0246(15) 0.0274(14) 0.0299(15) 0.0009(11) -0.0012(12) -0.0020(11)
C9 0.0325(18) 0.0267(14) 0.0302(16) 0.0018(13) -0.0038(13) 0.0003(13)
N1 0.0275(14) 0.0262(13) 0.0317(13) 0.0013(11) -0.0027(10) 0.0000(11)
O2 0.0411(15) 0.0315(11) 0.0421(13) -0.0013(10) -0.0101(11) 0.0009(10)
O1 0.0656(18) 0.0344(11) 0.0409(13) -0.0013(10) -0.0189(12) -0.0039(11)
C11 0.0259(18) 0.0296(14) 0.0316(17) -0.0001(12) 0.0030(13) -0.0020(12)
C10 0.0244(16) 0.0312(16) 0.0283(15) 0.0032(12) -0.0013(12) 0.0019(12)
C16 0.053(2) 0.0287(16) 0.0472(19) -0.0008(13) -0.0079(16) -0.0059(15)
C15 0.0317(16) 0.0287(14) 0.0319(15) -0.0002(14) 0.0014(13) 0.0004(14)
C13 0.0284(15) 0.0331(15) 0.0284(15) 0.0004(12) -0.0040(12) 0.0015(13)
C7 0.0358(17) 0.0311(15) 0.0308(16) -0.0032(12) -0.0044(13) -0.0028(14)
C1 0.0397(18) 0.0294(14) 0.0340(17) 0.0025(13) -0.0117(13) -0.0078(13)
C6 0.051(2) 0.0376(16) 0.0403(18) 0.0040(14) -0.0060(15) -0.0056(15)
C8 0.0341(19) 0.0292(14) 0.0279(14) 0.0000(12) -0.0002(13) -0.0005(13)
C12 0.0302(18) 0.0296(15) 0.0280(15) 0.0021(12) -0.0053(13) 0.0005(13)
C3 0.080(3) 0.0290(17) 0.073(3) 0.0025(17) -0.031(2) 0.0031(18)
C5 0.072(3) 0.050(2) 0.043(2) 0.0153(16) -0.0138(18) -0.019(2)
C2 0.064(3) 0.0280(16) 0.049(2) -0.0022(15) -0.0183(18) 0.0019(17)
C4 0.087(3) 0.0321(18) 0.067(3) 0.0168(18) -0.037(2) -0.0126(19)
O5 0.0390(13) 0.0264(10) 0.0403(12) -0.0010(9) -0.0103(10) 0.0028(9)
O4 0.0389(13) 0.0314(9) 0.0364(11) 0.0029(9) -0.0135(9) -0.0015(9)
O6 0.0348(13) 0.0263(10) 0.0452(13) 0.0027(10) -0.0114(10) 0.0017(9)
O7 0.0407(13) 0.0368(11) 0.0407(12) -0.0035(11) -0.0158(10) -0.0008(11)
C18 0.0295(17) 0.0265(14) 0.0281(16) 0.0012(13) -0.0041(13) -0.0034(13)
C17 0.0260(16) 0.0302(15) 0.0258(14) -0.0011(12) -0.0039(12) 0.0003(13)
C19 0.042(2) 0.0313(15) 0.053(2) 0.0065(14) -0.0135(16) 0.0043(15)

_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
N3 C14 1.357(4) . ?
N3 C15 1.375(4) . ?
N3 H3A 0.79(4) . ?
O3 C15 1.335(4) . ?
O3 C16 1.445(4) . ?
N2 C14 1.331(4) . ?
N2 C10 1.381(4) . ?
N2 H2A 1.07(4) . ?
C14 N1 1.340(4) . ?
C9 C10 1.387(4) . ?
C9 C8 1.394(5) . ?
C9 H9 0.9500 . ?
N1 C11 1.399(4) . ?
N1 H1A 0.84(5) . ?
O2 C15 1.200(4) . ?
O1 C7 1.232(4) . ?
C11 C10 1.387(4) . ?
C11 C12 1.392(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C13 C12 1.374(4) . ?
C13 C8 1.401(4) . ?
C13 H13 0.9500 . ?
C7 C8 1.489(4) . ?
C7 C1 1.496(5) . ?
C1 C2 1.388(5) . ?
C1 C6 1.400(5) . ?
C6 C5 1.382(5) . ?
C6 H6 0.9500 . ?
C12 H12 0.9500 . ?
C3 C4 1.373(7) . ?
C3 C2 1.385(5) . ?
C3 H3 0.9500 . ?
C5 C4 1.390(6) . ?
C5 H5 0.9500 . ?
C2 H2 0.9500 . ?
C4 H4 0.9500 . ?
O5 C17 1.245(4) . ?
O4 C17 1.259(4) . ?
O6 C18 1.323(4) . ?
O6 C19 1.442(4) . ?
O7 C18 1.197(4) . ?
C18 C17 1.548(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C14 N3 C15 123.7(3) . . ?
C14 N3 H3A 114(3) . . ?
C15 N3 H3A 122(3) . . ?
C15 O3 C16 115.0(3) . . ?
C14 N2 C10 107.2(3) . . ?
C14 N2 H2A 125.1(17) . . ?
C10 N2 H2A 127.7(17) . . ?
N2 C14 N1 111.0(3) . . ?
N2 C14 N3 122.4(3) . . ?
N1 C14 N3 126.6(3) . . ?
C10 C9 C8 116.6(3) . . ?
C10 C9 H9 121.7 . . ?
C8 C9 H9 121.7 . . ?
C14 N1 C11 107.7(3) . . ?
C14 N1 H1A 124(3) . . ?
C11 N1 H1A 128(3) . . ?
C10 C11 C12 122.0(3) . . ?
C10 C11 N1 105.7(3) . . ?
C12 C11 N1 132.2(3) . . ?
N2 C10 C11 108.4(2) . . ?
N2 C10 C9 129.8(3) . . ?
C11 C10 C9 121.8(3) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C15 O3 126.6(3) . . ?
O2 C15 N3 124.9(3) . . ?
O3 C15 N3 108.6(3) . . ?
C12 C13 C8 122.5(3) . . ?
C12 C13 H13 118.8 . . ?
C8 C13 H13 118.8 . . ?
O1 C7 C8 121.1(3) . . ?
O1 C7 C1 119.4(3) . . ?
C8 C7 C1 119.5(3) . . ?
C2 C1 C6 119.8(3) . . ?
C2 C1 C7 118.8(3) . . ?
C6 C1 C7 121.4(3) . . ?
C5 C6 C1 119.4(3) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C9 C8 C13 120.9(3) . . ?
C9 C8 C7 119.3(3) . . ?
C13 C8 C7 119.7(3) . . ?
C13 C12 C11 116.2(3) . . ?
C13 C12 H12 121.9 . . ?
C11 C12 H12 121.9 . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C18 O6 C19 116.2(2) . . ?
O7 C18 O6 125.3(3) . . ?
O7 C18 C17 123.0(3) . . ?
O6 C18 C17 111.7(2) . . ?
O5 C17 O4 127.7(3) . . ?
O5 C17 C18 116.3(3) . . ?
O4 C17 C18 116.0(2) . . ?
O6 C19 H19A 109.5 . . ?
O6 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O6 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O4 1.07(4) 1.50(4) 2.559(3) 174(3) .
N3 H3A O5 0.79(4) 2.01(4) 2.797(4) 170(4) .
N1 H1A O2 0.84(5) 2.25(5) 2.751(3) 119(4) .
N1 H1A O7 0.84(5) 2.13(5) 2.798(3) 136(4) 2_364

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        65.07
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.037

# Attachment '- 2.cif'

data_cjm1
_database_code_depnum_ccdc_archive 'CCDC 866969'
#TrackingRef '- 2.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 N3 O7'
_chemical_formula_weight         411.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   8.3845(3)
_cell_length_b                   8.9098(4)
_cell_length_c                   13.2841(7)
_cell_angle_alpha                83.810(4)
_cell_angle_beta                 80.223(4)
_cell_angle_gamma                84.612(3)
_cell_volume                     969.37(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3904
_cell_measurement_theta_min      3.3881
_cell_measurement_theta_max      72.3236

_exptl_crystal_description       Needle
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7272
_exptl_absorpt_correction_T_max  0.8304
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Nova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6857
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.39
_diffrn_reflns_theta_max         66.58
_reflns_number_total             4199
_reflns_number_gt                3792
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond Version 3.1a'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.0665P)^2^+0.1679P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_number_reflns         4199
_refine_ls_number_parameters     569
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1161
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_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
C12 C 0.2084(4) 1.0552(3) 0.1228(2) 0.0320(6) Uani 1 1 d . . .
C13 C 0.2479(4) 0.9630(4) 0.2067(2) 0.0338(7) Uani 1 1 d . . .
H13 H 0.3249 0.8780 0.1992 0.041 Uiso 1 1 calc R . .
C8 C 0.1694(4) 1.0006(4) 0.3035(2) 0.0361(7) Uani 1 1 d . . .
C9 C 0.0566(4) 1.1269(4) 0.3124(3) 0.0383(7) Uani 1 1 d . . .
H9 H 0.0086 1.1525 0.3790 0.046 Uiso 1 1 calc R . .
C10 C 0.0130(4) 1.2150(4) 0.2288(2) 0.0368(7) Uani 1 1 d . . .
H10 H -0.0669 1.2978 0.2360 0.044 Uiso 1 1 calc R . .
C11 C 0.0916(4) 1.1771(4) 0.1324(2) 0.0347(7) Uani 1 1 d . . .
C14 C 0.1849(4) 1.1632(3) -0.0320(2) 0.0337(7) Uani 1 1 d . . .
C7 C 0.2094(4) 0.9149(4) 0.3998(2) 0.0371(7) Uani 1 1 d . . .
C1 C 0.2216(4) 0.7459(4) 0.4129(3) 0.0400(7) Uani 1 1 d . . .
C2 C 0.2681(5) 0.6726(4) 0.5022(3) 0.0502(9) Uani 1 1 d . . .
H2 H 0.2962 0.7308 0.5515 0.060 Uiso 1 1 calc R . .
C3 C 0.2744(6) 0.5171(5) 0.5207(3) 0.0597(10) Uani 1 1 d . . .
H3 H 0.3052 0.4691 0.5827 0.072 Uiso 1 1 calc R . .
C4 C 0.2355(6) 0.4311(5) 0.4486(4) 0.0571(10) Uani 1 1 d . . .
H4 H 0.2393 0.3239 0.4610 0.069 Uiso 1 1 calc R . .
C5 C 0.1914(5) 0.5014(4) 0.3592(3) 0.0498(9) Uani 1 1 d . . .
H5 H 0.1668 0.4422 0.3093 0.060 Uiso 1 1 calc R . .
C6 C 0.1824(4) 0.6580(4) 0.3410(3) 0.0426(7) Uani 1 1 d . . .
H6 H 0.1496 0.7055 0.2795 0.051 Uiso 1 1 calc R . .
C15 C 0.3222(4) 1.1266(4) -0.2019(3) 0.0366(7) Uani 1 1 d . . .
C16 C 0.4472(5) 1.1236(5) -0.3715(3) 0.0525(9) Uani 1 1 d . . .
H16A H 0.5526 1.1415 -0.3544 0.079 Uiso 1 1 calc R . .
H16B H 0.4377 1.1721 -0.4403 0.079 Uiso 1 1 calc R . .
H16C H 0.4386 1.0144 -0.3701 0.079 Uiso 1 1 calc R . .
C32 C 0.7493(3) 0.9941(3) 0.1438(2) 0.0313(6) Uani 1 1 d . . .
C33 C 0.7817(4) 0.9046(4) 0.2302(2) 0.0336(6) Uani 1 1 d . . .
H33 H 0.8580 0.8187 0.2262 0.040 Uiso 1 1 calc R . .
C28 C 0.6960(4) 0.9468(4) 0.3246(2) 0.0355(7) Uani 1 1 d . . .
C29 C 0.5855(4) 1.0727(4) 0.3292(3) 0.0388(7) Uani 1 1 d . . .
H29 H 0.5335 1.0999 0.3947 0.047 Uiso 1 1 calc R . .
C30 C 0.5474(4) 1.1605(4) 0.2432(2) 0.0367(7) Uani 1 1 d . . .
H30 H 0.4685 1.2444 0.2474 0.044 Uiso 1 1 calc R . .
C31 C 0.6329(4) 1.1176(4) 0.1487(2) 0.0359(7) Uani 1 1 d . . .
C34 C 0.7335(4) 1.0987(4) -0.0132(2) 0.0345(7) Uani 1 1 d . . .
C27 C 0.7267(4) 0.8626(4) 0.4237(2) 0.0391(8) Uani 1 1 d . . .
C21 C 0.7401(4) 0.6952(4) 0.4377(3) 0.0409(7) Uani 1 1 d . . .
C22 C 0.8002(5) 0.6228(5) 0.5233(3) 0.0529(9) Uani 1 1 d . . .
H22 H 0.8387 0.6814 0.5685 0.063 Uiso 1 1 calc R . .
C23 C 0.8050(6) 0.4671(5) 0.5437(4) 0.0661(12) Uani 1 1 d . . .
H23 H 0.8451 0.4193 0.6029 0.079 Uiso 1 1 calc R . .
C24 C 0.7506(5) 0.3813(5) 0.4769(4) 0.0629(12) Uani 1 1 d . . .
H24 H 0.7529 0.2742 0.4904 0.076 Uiso 1 1 calc R . .
C25 C 0.6936(5) 0.4510(5) 0.3913(3) 0.0545(10) Uani 1 1 d . . .
H25 H 0.6583 0.3911 0.3456 0.065 Uiso 1 1 calc R . .
C26 C 0.6865(4) 0.6075(4) 0.3702(3) 0.0449(8) Uani 1 1 d . . .
H26 H 0.6460 0.6545 0.3110 0.054 Uiso 1 1 calc R . .
C35 C 0.8695(4) 1.0583(4) -0.1842(3) 0.0354(7) Uani 1 1 d . . .
C36 C 0.9724(5) 1.0488(5) -0.3590(3) 0.0540(10) Uani 1 1 d . . .
H36A H 1.0752 1.0931 -0.3594 0.081 Uiso 1 1 calc R . .
H36B H 0.9376 1.0738 -0.4260 0.081 Uiso 1 1 calc R . .
H36C H 0.9873 0.9386 -0.3450 0.081 Uiso 1 1 calc R . .
N2 N 0.0769(3) 1.2409(3) 0.0339(2) 0.0343(6) Uani 1 1 d D . .
N1 N 0.2636(4) 1.0519(3) 0.0180(2) 0.0355(6) Uani 1 1 d D . .
N3 N 0.2024(3) 1.2012(3) -0.1351(2) 0.0354(6) Uani 1 1 d . . .
N5 N 0.6243(3) 1.1798(3) 0.0496(2) 0.0360(6) Uani 1 1 d . . .
N4 N 0.8115(3) 0.9888(3) 0.0395(2) 0.0340(6) Uani 1 1 d . . .
N6 N 0.7515(4) 1.1322(3) -0.1166(2) 0.0384(6) Uani 1 1 d . . .
O1 O 0.2246(3) 0.9871(3) 0.47099(18) 0.0476(6) Uani 1 1 d . . .
O2 O 0.4137(3) 1.0238(3) -0.17474(18) 0.0437(6) Uani 1 1 d . . .
O3 O 0.3180(3) 1.1869(3) -0.29716(17) 0.0424(6) Uani 1 1 d . . .
O8 O 0.7327(4) 0.9372(3) 0.49569(19) 0.0524(7) Uani 1 1 d . . .
O9 O 0.9693(3) 0.9643(3) -0.15771(18) 0.0432(6) Uani 1 1 d . . .
O10 O 0.8493(3) 1.1097(3) -0.27957(18) 0.0461(6) Uani 1 1 d . . .
H6A H 0.688(4) 1.205(4) -0.135(2) 0.015(7) Uiso 1 1 d . . .
H1A H 0.337(5) 0.992(5) -0.011(4) 0.064(14) Uiso 1 1 d D . .
H4A H 0.899(5) 0.913(5) 0.010(3) 0.047(11) Uiso 1 1 d . . .
H5A H 0.558(5) 1.267(5) 0.021(3) 0.047(11) Uiso 1 1 d . . .
H2A H 0.009(5) 1.316(4) 0.009(4) 0.060(13) Uiso 1 1 d D . .
H3A H 0.119(6) 1.286(5) -0.162(4) 0.055(12) Uiso 1 1 d . . .
C20 C -0.3926(4) 1.7258(4) 0.0035(3) 0.0384(7) Uani 1 1 d . . .
C19 C -0.3336(4) 1.7218(4) -0.1081(3) 0.0405(8) Uani 1 1 d . . .
H19 H -0.3840 1.7987 -0.1501 0.049 Uiso 1 1 calc R . .
C18 C -0.2208(4) 1.6283(4) -0.1606(3) 0.0387(7) Uani 1 1 d . . .
H18 H -0.2058 1.6505 -0.2330 0.046 Uiso 1 1 calc R . .
C17 C -0.1164(4) 1.4965(4) -0.1239(3) 0.0386(7) Uani 1 1 d . . .
O6 O -0.3274(3) 1.6357(3) 0.07144(19) 0.0486(6) Uani 1 1 d . . .
H6B H -0.2651 1.5685 0.0421 0.073 Uiso 1 1 calc R . .
O7 O -0.5039(3) 1.8203(3) 0.0303(2) 0.0463(6) Uani 1 1 d . . .
O4 O -0.1227(3) 1.4639(3) -0.02737(18) 0.0476(6) Uani 1 1 d . . .
O5 O -0.0241(3) 1.4265(3) -0.18962(19) 0.0466(6) Uani 1 1 d . . .
C40 C 0.1540(4) 1.6637(4) 0.0230(3) 0.0377(7) Uani 1 1 d . . .
C39 C 0.2171(4) 1.6616(4) -0.0889(3) 0.0425(8) Uani 1 1 d . . .
H39 H 0.1682 1.7396 -0.1308 0.051 Uiso 1 1 calc R . .
C38 C 0.3303(4) 1.5697(4) -0.1414(3) 0.0386(7) Uani 1 1 d . . .
H38 H 0.3455 1.5925 -0.2138 0.046 Uiso 1 1 calc R . .
C37 C 0.4360(4) 1.4380(4) -0.1051(3) 0.0371(7) Uani 1 1 d . . .
O14 O 0.0500(3) 1.7620(3) 0.0505(2) 0.0489(6) Uani 1 1 d . . .
O13 O 0.2071(3) 1.5623(3) 0.09009(19) 0.0476(6) Uani 1 1 d . . .
H13B H 0.2821 1.5057 0.0603 0.071 Uiso 1 1 calc R . .
O11 O 0.4239(3) 1.4017(3) -0.00796(18) 0.0449(6) Uani 1 1 d . . .
O12 O 0.5313(3) 1.3698(3) -0.17017(19) 0.0436(6) 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
C12 0.0300(15) 0.0327(16) 0.0303(16) -0.0077(12) 0.0063(12) -0.0029(12)
C13 0.0364(16) 0.0312(15) 0.0320(16) -0.0081(12) 0.0040(12) -0.0052(12)
C8 0.0362(17) 0.0388(17) 0.0327(16) -0.0096(13) 0.0041(13) -0.0099(13)
C9 0.0375(17) 0.0390(18) 0.0371(17) -0.0138(14) 0.0065(14) -0.0077(14)
C10 0.0359(17) 0.0367(17) 0.0355(17) -0.0151(13) 0.0078(13) -0.0017(13)
C11 0.0370(16) 0.0346(16) 0.0326(17) -0.0079(13) 0.0007(13) -0.0086(13)
C14 0.0375(17) 0.0305(16) 0.0315(16) -0.0080(12) 0.0041(13) -0.0059(13)
C7 0.0334(16) 0.0446(18) 0.0308(16) -0.0112(14) 0.0078(12) -0.0051(13)
C1 0.0364(17) 0.0449(18) 0.0357(16) -0.0033(13) 0.0031(13) -0.0051(13)
C2 0.059(2) 0.053(2) 0.0368(18) -0.0056(15) -0.0049(16) -0.0005(18)
C3 0.075(3) 0.056(2) 0.046(2) 0.0025(17) -0.0101(19) 0.003(2)
C4 0.063(3) 0.041(2) 0.063(3) 0.0036(17) -0.004(2) 0.0010(18)
C5 0.052(2) 0.042(2) 0.054(2) -0.0085(17) -0.0045(17) -0.0047(17)
C6 0.0432(18) 0.0419(18) 0.0414(18) -0.0068(14) -0.0007(14) -0.0049(14)
C15 0.0415(18) 0.0338(17) 0.0327(17) -0.0065(13) 0.0021(14) -0.0045(14)
C16 0.054(2) 0.068(2) 0.0308(18) -0.0113(16) 0.0042(15) 0.0065(18)
C32 0.0239(14) 0.0348(15) 0.0339(16) -0.0134(13) 0.0041(12) -0.0005(11)
C33 0.0388(17) 0.0334(15) 0.0281(15) -0.0092(12) -0.0006(12) -0.0022(12)
C28 0.0338(16) 0.0388(17) 0.0350(16) -0.0100(13) -0.0009(13) -0.0090(13)
C29 0.0375(17) 0.0414(17) 0.0367(18) -0.0141(14) 0.0052(14) -0.0066(13)
C30 0.0345(17) 0.0396(17) 0.0342(17) -0.0140(14) 0.0048(13) -0.0004(13)
C31 0.0373(17) 0.0381(16) 0.0330(17) -0.0092(13) -0.0012(13) -0.0072(13)
C34 0.0359(17) 0.0336(16) 0.0333(16) -0.0106(13) 0.0030(13) -0.0059(13)
C27 0.0409(18) 0.048(2) 0.0288(17) -0.0105(14) 0.0004(13) -0.0079(15)
C21 0.0401(17) 0.0415(18) 0.0366(17) -0.0047(13) 0.0061(13) -0.0015(14)
C22 0.061(2) 0.058(2) 0.0348(18) -0.0008(16) -0.0002(16) 0.0025(18)
C23 0.080(3) 0.055(2) 0.052(2) 0.0055(19) 0.009(2) 0.008(2)
C24 0.053(2) 0.048(2) 0.074(3) 0.004(2) 0.018(2) 0.0059(18)
C25 0.053(2) 0.044(2) 0.062(3) -0.0115(19) 0.0116(19) -0.0096(18)
C26 0.0390(18) 0.0432(19) 0.050(2) -0.0102(15) 0.0049(14) -0.0055(15)
C35 0.0397(17) 0.0361(17) 0.0304(16) -0.0110(13) 0.0029(13) -0.0094(14)
C36 0.048(2) 0.076(3) 0.0361(19) -0.0179(18) 0.0033(16) 0.0008(19)
N2 0.0338(15) 0.0322(14) 0.0356(15) -0.0061(11) -0.0001(11) -0.0017(11)
N1 0.0414(15) 0.0342(14) 0.0291(14) -0.0109(11) 0.0048(11) -0.0045(12)
N3 0.0377(14) 0.0357(14) 0.0304(14) -0.0064(11) 0.0035(11) -0.0029(11)
N5 0.0372(15) 0.0345(14) 0.0342(15) -0.0073(11) 0.0009(11) 0.0002(12)
N4 0.0373(15) 0.0356(14) 0.0282(13) -0.0078(11) 0.0009(11) -0.0040(11)
N6 0.0396(15) 0.0375(15) 0.0346(15) -0.0057(12) 0.0042(12) -0.0002(13)
O1 0.0570(15) 0.0541(15) 0.0318(12) -0.0141(10) 0.0011(10) -0.0079(12)
O2 0.0539(15) 0.0428(13) 0.0308(12) -0.0074(10) 0.0036(11) 0.0011(12)
O3 0.0449(14) 0.0513(14) 0.0292(12) -0.0094(10) 0.0001(10) 0.0006(11)
O8 0.0719(18) 0.0520(15) 0.0358(13) -0.0148(11) -0.0107(12) -0.0019(13)
O9 0.0422(13) 0.0479(14) 0.0377(13) -0.0098(11) -0.0004(10) 0.0017(11)
O10 0.0458(14) 0.0610(16) 0.0292(12) -0.0111(11) 0.0014(10) 0.0020(12)
C20 0.0390(18) 0.0357(18) 0.0398(18) -0.0077(14) -0.0010(14) -0.0036(14)
C19 0.0391(18) 0.0404(18) 0.0415(19) -0.0047(14) -0.0037(14) -0.0045(14)
C18 0.0371(18) 0.0423(18) 0.0342(17) -0.0059(14) 0.0010(13) 0.0001(14)
C17 0.0369(17) 0.0412(17) 0.0376(18) -0.0114(14) 0.0012(13) -0.0060(14)
O6 0.0555(16) 0.0487(15) 0.0381(14) -0.0078(11) -0.0027(12) 0.0098(12)
O7 0.0456(14) 0.0442(13) 0.0468(14) -0.0116(11) -0.0021(11) 0.0069(11)
O4 0.0523(15) 0.0522(15) 0.0335(13) -0.0059(11) -0.0010(10) 0.0122(11)
O5 0.0473(14) 0.0508(15) 0.0407(13) -0.0146(11) -0.0024(11) 0.0051(11)
C40 0.0332(16) 0.0351(17) 0.0439(19) -0.0133(14) -0.0003(14) 0.0031(13)
C39 0.0430(19) 0.0442(19) 0.0400(19) -0.0044(15) -0.0059(14) -0.0033(15)
C38 0.0372(18) 0.0400(18) 0.0355(18) -0.0070(14) 0.0018(14) 0.0031(14)
C37 0.0370(18) 0.0378(17) 0.0370(18) -0.0105(13) 0.0002(13) -0.0087(14)
O14 0.0518(15) 0.0450(14) 0.0469(14) -0.0095(11) -0.0012(11) 0.0057(12)
O13 0.0552(15) 0.0438(14) 0.0391(13) -0.0048(10) -0.0010(11) 0.0092(11)
O11 0.0489(15) 0.0455(14) 0.0358(13) -0.0056(10) -0.0006(10) 0.0101(11)
O12 0.0458(14) 0.0406(13) 0.0434(13) -0.0122(11) 0.0003(11) -0.0016(11)

_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
C12 C13 1.380(5) . ?
C12 N1 1.393(4) . ?
C12 C11 1.394(5) . ?
C13 C8 1.400(4) . ?
C13 H13 0.9500 . ?
C8 C9 1.402(5) . ?
C8 C7 1.490(5) . ?
C9 C10 1.372(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.398(4) . ?
C10 H10 0.9500 . ?
C11 N2 1.389(5) . ?
C14 N1 1.320(5) . ?
C14 N2 1.346(4) . ?
C14 N3 1.360(4) . ?
C7 O1 1.230(4) . ?
C7 C1 1.493(5) . ?
C1 C2 1.389(5) . ?
C1 C6 1.396(5) . ?
C2 C3 1.378(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.373(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C15 O2 1.203(4) . ?
C15 O3 1.325(4) . ?
C15 N3 1.392(4) . ?
C16 O3 1.453(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C32 C33 1.377(5) . ?
C32 N4 1.399(4) . ?
C32 C31 1.399(5) . ?
C33 C28 1.406(4) . ?
C33 H33 0.9500 . ?
C28 C29 1.386(5) . ?
C28 C27 1.493(5) . ?
C29 C30 1.379(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.408(5) . ?
C30 H30 0.9500 . ?
C31 N5 1.382(4) . ?
C34 N4 1.329(5) . ?
C34 N5 1.343(4) . ?
C34 N6 1.359(5) . ?
C27 O8 1.233(4) . ?
C27 C21 1.479(5) . ?
C21 C22 1.391(5) . ?
C21 C26 1.404(5) . ?
C22 C23 1.382(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(8) . ?
C23 H23 0.9500 . ?
C24 C25 1.372(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.390(6) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C35 O9 1.196(4) . ?
C35 O10 1.333(4) . ?
C35 N6 1.386(5) . ?
C36 O10 1.457(4) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
N2 H2A 0.91(2) . ?
N1 H1A 0.85(2) . ?
N3 H3A 1.06(5) . ?
N5 H5A 0.99(5) . ?
N4 H4A 1.01(5) . ?
N6 H6A 0.84(3) . ?
C20 O7 1.229(4) . ?
C20 O6 1.299(5) . ?
C20 C19 1.484(5) . ?
C19 C18 1.352(5) . ?
C19 H19 0.9500 . ?
C18 C17 1.488(5) . ?
C18 H18 0.9500 . ?
C17 O5 1.243(4) . ?
C17 O4 1.277(4) . ?
O6 H6B 0.8400 . ?
C40 O14 1.216(4) . ?
C40 O13 1.302(4) . ?
C40 C39 1.492(5) . ?
C39 C38 1.346(5) . ?
C39 H39 0.9500 . ?
C38 C37 1.490(5) . ?
C38 H38 0.9500 . ?
C37 O12 1.242(4) . ?
C37 O11 1.285(4) . ?
O13 H13B 0.8400 . ?

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
C13 C12 N1 131.8(3) . . ?
C13 C12 C11 122.2(3) . . ?
N1 C12 C11 105.9(3) . . ?
C12 C13 C8 116.9(3) . . ?
C12 C13 H13 121.5 . . ?
C8 C13 H13 121.5 . . ?
C13 C8 C9 120.4(3) . . ?
C13 C8 C7 121.7(3) . . ?
C9 C8 C7 117.8(3) . . ?
C10 C9 C8 122.6(3) . . ?
C10 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
C9 C10 C11 116.8(3) . . ?
C9 C10 H10 121.6 . . ?
C11 C10 H10 121.6 . . ?
N2 C11 C12 107.4(3) . . ?
N2 C11 C10 131.6(3) . . ?
C12 C11 C10 121.0(3) . . ?
N1 C14 N2 110.5(3) . . ?
N1 C14 N3 128.1(3) . . ?
N2 C14 N3 121.4(3) . . ?
O1 C7 C8 118.2(3) . . ?
O1 C7 C1 120.3(3) . . ?
C8 C7 C1 121.5(3) . . ?
C2 C1 C6 118.3(3) . . ?
C2 C1 C7 118.7(3) . . ?
C6 C1 C7 122.9(3) . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.7(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.7(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.1(4) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O2 C15 O3 126.8(3) . . ?
O2 C15 N3 123.8(3) . . ?
O3 C15 N3 109.4(3) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C33 C32 N4 132.4(3) . . ?
C33 C32 C31 122.1(3) . . ?
N4 C32 C31 105.5(3) . . ?
C32 C33 C28 116.5(3) . . ?
C32 C33 H33 121.7 . . ?
C28 C33 H33 121.7 . . ?
C29 C28 C33 121.0(3) . . ?
C29 C28 C27 117.6(3) . . ?
C33 C28 C27 121.3(3) . . ?
C30 C29 C28 123.2(3) . . ?
C30 C29 H29 118.4 . . ?
C28 C29 H29 118.4 . . ?
C29 C30 C31 115.6(3) . . ?
C29 C30 H30 122.2 . . ?
C31 C30 H30 122.2 . . ?
N5 C31 C32 108.1(3) . . ?
N5 C31 C30 130.4(3) . . ?
C32 C31 C30 121.5(3) . . ?
N4 C34 N5 111.1(3) . . ?
N4 C34 N6 128.2(3) . . ?
N5 C34 N6 120.6(3) . . ?
O8 C27 C21 120.6(3) . . ?
O8 C27 C28 117.7(3) . . ?
C21 C27 C28 121.6(3) . . ?
C22 C21 C26 119.0(3) . . ?
C22 C21 C27 118.9(3) . . ?
C26 C21 C27 122.0(3) . . ?
C23 C22 C21 121.3(4) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C24 119.3(4) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C25 C24 C23 120.0(4) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 121.4(4) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C25 C26 C21 119.0(4) . . ?
C25 C26 H26 120.5 . . ?
C21 C26 H26 120.5 . . ?
O9 C35 O10 127.9(3) . . ?
O9 C35 N6 123.8(3) . . ?
O10 C35 N6 108.3(3) . . ?
O10 C36 H36A 109.5 . . ?
O10 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O10 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C14 N2 C11 107.4(3) . . ?
C14 N2 H2A 120(3) . . ?
C11 N2 H2A 133(3) . . ?
C14 N1 C12 108.8(3) . . ?
C14 N1 H1A 124(4) . . ?
C12 N1 H1A 127(4) . . ?
C14 N3 C15 120.8(3) . . ?
C14 N3 H3A 117(3) . . ?
C15 N3 H3A 122(3) . . ?
C34 N5 C31 107.0(3) . . ?
C34 N5 H5A 120(3) . . ?
C31 N5 H5A 133(3) . . ?
C34 N4 C32 108.3(3) . . ?
C34 N4 H4A 127(2) . . ?
C32 N4 H4A 125(2) . . ?
C34 N6 C35 122.8(3) . . ?
C34 N6 H6A 114(2) . . ?
C35 N6 H6A 123(2) . . ?
C15 O3 C16 113.2(3) . . ?
C35 O10 C36 114.2(3) . . ?
O7 C20 O6 120.5(3) . . ?
O7 C20 C19 117.7(3) . . ?
O6 C20 C19 121.8(3) . . ?
C18 C19 C20 131.5(3) . . ?
C18 C19 H19 114.3 . . ?
C20 C19 H19 114.3 . . ?
C19 C18 C17 130.8(3) . . ?
C19 C18 H18 114.6 . . ?
C17 C18 H18 114.6 . . ?
O5 C17 O4 123.7(4) . . ?
O5 C17 C18 117.7(3) . . ?
O4 C17 C18 118.6(3) . . ?
C20 O6 H6B 109.5 . . ?
C17 O4 H2A 116.0(17) . . ?
O14 C40 O13 120.3(3) . . ?
O14 C40 C39 118.4(3) . . ?
O13 C40 C39 121.3(3) . . ?
C38 C39 C40 131.9(3) . . ?
C38 C39 H39 114.0 . . ?
C40 C39 H39 114.0 . . ?
C39 C38 C37 130.8(3) . . ?
C39 C38 H38 114.6 . . ?
C37 C38 H38 114.6 . . ?
O12 C37 O11 123.6(3) . . ?
O12 C37 C38 118.4(3) . . ?
O11 C37 C38 118.1(3) . . ?
C40 O13 H13B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C12 C13 C8 179.1(3) . . . . ?
C11 C12 C13 C8 -2.3(4) . . . . ?
C12 C13 C8 C9 -0.2(4) . . . . ?
C12 C13 C8 C7 -176.3(3) . . . . ?
C13 C8 C9 C10 2.7(5) . . . . ?
C7 C8 C9 C10 179.0(3) . . . . ?
C8 C9 C10 C11 -2.6(5) . . . . ?
C13 C12 C11 N2 -177.5(3) . . . . ?
N1 C12 C11 N2 1.5(3) . . . . ?
C13 C12 C11 C10 2.4(5) . . . . ?
N1 C12 C11 C10 -178.6(3) . . . . ?
C9 C10 C11 N2 180.0(3) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C13 C8 C7 O1 136.0(3) . . . . ?
C9 C8 C7 O1 -40.2(4) . . . . ?
C13 C8 C7 C1 -47.5(4) . . . . ?
C9 C8 C7 C1 136.2(3) . . . . ?
O1 C7 C1 C2 -7.1(5) . . . . ?
C8 C7 C1 C2 176.5(3) . . . . ?
O1 C7 C1 C6 170.4(3) . . . . ?
C8 C7 C1 C6 -6.0(5) . . . . ?
C6 C1 C2 C3 -0.6(6) . . . . ?
C7 C1 C2 C3 177.0(4) . . . . ?
C1 C2 C3 C4 0.7(7) . . . . ?
C2 C3 C4 C5 0.2(7) . . . . ?
C3 C4 C5 C6 -1.2(6) . . . . ?
C4 C5 C6 C1 1.3(6) . . . . ?
C2 C1 C6 C5 -0.4(5) . . . . ?
C7 C1 C6 C5 -177.9(3) . . . . ?
N4 C32 C33 C28 178.7(3) . . . . ?
C31 C32 C33 C28 -2.3(4) . . . . ?
C32 C33 C28 C29 -0.3(4) . . . . ?
C32 C33 C28 C27 -177.1(3) . . . . ?
C33 C28 C29 C30 2.6(5) . . . . ?
C27 C28 C29 C30 179.6(3) . . . . ?
C28 C29 C30 C31 -2.3(5) . . . . ?
C33 C32 C31 N5 -177.5(3) . . . . ?
N4 C32 C31 N5 1.7(3) . . . . ?
C33 C32 C31 C30 2.7(5) . . . . ?
N4 C32 C31 C30 -178.1(3) . . . . ?
C29 C30 C31 N5 179.9(3) . . . . ?
C29 C30 C31 C32 -0.3(4) . . . . ?
C29 C28 C27 O8 -38.9(4) . . . . ?
C33 C28 C27 O8 138.1(3) . . . . ?
C29 C28 C27 C21 137.6(3) . . . . ?
C33 C28 C27 C21 -45.5(5) . . . . ?
O8 C27 C21 C22 -16.3(5) . . . . ?
C28 C27 C21 C22 167.4(3) . . . . ?
O8 C27 C21 C26 160.5(3) . . . . ?
C28 C27 C21 C26 -15.9(5) . . . . ?
C26 C21 C22 C23 -1.3(6) . . . . ?
C27 C21 C22 C23 175.6(4) . . . . ?
C21 C22 C23 C24 0.8(6) . . . . ?
C22 C23 C24 C25 0.3(6) . . . . ?
C23 C24 C25 C26 -1.0(6) . . . . ?
C24 C25 C26 C21 0.5(6) . . . . ?
C22 C21 C26 C25 0.6(5) . . . . ?
C27 C21 C26 C25 -176.1(3) . . . . ?
N1 C14 N2 C11 1.7(4) . . . . ?
N3 C14 N2 C11 -178.5(3) . . . . ?
C12 C11 N2 C14 -2.0(3) . . . . ?
C10 C11 N2 C14 178.1(3) . . . . ?
N2 C14 N1 C12 -0.8(4) . . . . ?
N3 C14 N1 C12 179.5(3) . . . . ?
C13 C12 N1 C14 178.4(3) . . . . ?
C11 C12 N1 C14 -0.4(3) . . . . ?
N1 C14 N3 C15 -4.8(5) . . . . ?
N2 C14 N3 C15 175.5(3) . . . . ?
O2 C15 N3 C14 1.9(5) . . . . ?
O3 C15 N3 C14 -178.0(3) . . . . ?
N4 C34 N5 C31 -0.2(4) . . . . ?
N6 C34 N5 C31 179.1(3) . . . . ?
C32 C31 N5 C34 -1.0(3) . . . . ?
C30 C31 N5 C34 178.8(3) . . . . ?
N5 C34 N4 C32 1.2(3) . . . . ?
N6 C34 N4 C32 -177.9(3) . . . . ?
C33 C32 N4 C34 177.3(3) . . . . ?
C31 C32 N4 C34 -1.8(3) . . . . ?
N4 C34 N6 C35 -5.2(5) . . . . ?
N5 C34 N6 C35 175.7(3) . . . . ?
O9 C35 N6 C34 -3.4(5) . . . . ?
O10 C35 N6 C34 176.2(3) . . . . ?
O2 C15 O3 C16 -4.3(5) . . . . ?
N3 C15 O3 C16 175.6(3) . . . . ?
O9 C35 O10 C36 -4.4(5) . . . . ?
N6 C35 O10 C36 176.1(3) . . . . ?
O7 C20 C19 C18 -176.4(4) . . . . ?
O6 C20 C19 C18 5.3(6) . . . . ?
C20 C19 C18 C17 -0.1(7) . . . . ?
C19 C18 C17 O5 178.2(3) . . . . ?
C19 C18 C17 O4 -3.7(6) . . . . ?
O14 C40 C39 C38 179.5(4) . . . . ?
O13 C40 C39 C38 -1.2(6) . . . . ?
C40 C39 C38 C37 -1.5(7) . . . . ?
C39 C38 C37 O12 179.3(4) . . . . ?
C39 C38 C37 O11 -1.0(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O13 H13B O11 0.84 1.64 2.481(3) 174.7 .
O6 H6B O4 0.84 1.66 2.487(3) 168.9 .
N6 H6A O12 0.84(3) 1.95(4) 2.790(4) 176(3) .
N4 H4A O9 1.01(5) 2.22(4) 2.748(4) 111(3) .
N4 H4A O14 1.01(5) 1.86(4) 2.716(4) 141(4) 1_645
N5 H5A O11 0.99(5) 1.63(5) 2.609(4) 169(4) .
N3 H3A O5 1.06(5) 1.71(5) 2.757(4) 173(4) .
N1 H1A O2 0.85(2) 2.16(5) 2.681(3) 120(4) .
N1 H1A O7 0.85(2) 2.02(4) 2.714(4) 138(5) 1_645
N2 H2A O4 0.91(2) 1.72(2) 2.627(4) 175(5) .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        66.58
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.048

# Attachment '- 4.cif'

data_0711_cjm_110701_4a_2
_database_code_depnum_ccdc_archive 'CCDC 866970'
#TrackingRef '- 4.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 N3 O7'
_chemical_formula_weight         427.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   6.2151(3)
_cell_length_b                   10.7634(8)
_cell_length_c                   15.0123(9)
_cell_angle_alpha                85.260(5)
_cell_angle_beta                 87.897(5)
_cell_angle_gamma                81.635(5)
_cell_volume                     989.86(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2892
_cell_measurement_theta_min      2.9522
_cell_measurement_theta_max      66.6602

_exptl_crystal_description       Needle
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9137
_exptl_absorpt_correction_T_max  0.9555
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 10.5058
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6939
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         65.09
_reflns_number_total             3361
_reflns_number_gt                2756
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond 3.1a'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.0571P)^2^+0.0885P] 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         3361
_refine_ls_number_parameters     297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
O3 O -0.6187(2) 0.83785(13) 0.09858(9) 0.0442(3) Uani 1 1 d . . .
N2 N -0.0792(2) 0.60873(14) 0.26285(9) 0.0330(3) Uani 1 1 d . . .
O2 O -0.3284(2) 0.75627(15) 0.01593(9) 0.0501(4) Uani 1 1 d . . .
N1 N -0.0006(2) 0.62141(14) 0.11580(11) 0.0333(3) Uani 1 1 d . . .
N3 N -0.3428(2) 0.72613(14) 0.16869(10) 0.0342(3) Uani 1 1 d . . .
O1 O 0.80082(19) 0.39228(13) 0.07449(8) 0.0411(3) Uani 1 1 d . . .
C12 C 0.1756(3) 0.54607(16) 0.15612(11) 0.0313(4) Uani 1 1 d . . .
C11 C 0.1249(3) 0.54025(16) 0.24776(11) 0.0311(4) Uani 1 1 d . . .
C14 C -0.1447(3) 0.65344(15) 0.18124(11) 0.0304(4) Uani 1 1 d . . .
C2 C 1.0379(3) 0.18457(18) 0.17537(12) 0.0350(4) Uani 1 1 d . . .
H2 H 1.1296 0.2414 0.1487 0.042 Uiso 1 1 calc R . .
C8 C 0.5113(3) 0.41425(16) 0.18075(12) 0.0323(4) Uani 1 1 d . . .
C6 C 0.6832(3) 0.13879(17) 0.22524(11) 0.0329(4) Uani 1 1 d . . .
H6 H 0.5321 0.1656 0.2343 0.039 Uiso 1 1 calc R . .
C1 C 0.8152(3) 0.22320(16) 0.18551(11) 0.0307(4) Uani 1 1 d . . .
C7 C 0.7168(3) 0.34816(17) 0.14300(11) 0.0328(4) Uani 1 1 d . . .
C3 C 1.1249(3) 0.06261(18) 0.20450(13) 0.0399(4) Uani 1 1 d . . .
H3A H 1.2773 0.0368 0.1991 0.048 Uiso 1 1 calc R . .
C4 C 0.9923(3) -0.02172(18) 0.24127(12) 0.0407(4) Uani 1 1 d . . .
H4 H 1.0532 -0.1057 0.2595 0.049 Uiso 1 1 calc R . .
C5 C 0.7711(3) 0.01596(18) 0.25157(12) 0.0375(4) Uani 1 1 d . . .
H5 H 0.6797 -0.0421 0.2766 0.045 Uiso 1 1 calc R . .
C15 C -0.4216(3) 0.77212(17) 0.08656(12) 0.0350(4) Uani 1 1 d . . .
C13 C 0.3656(3) 0.48506(16) 0.12074(12) 0.0334(4) Uani 1 1 d . . .
H13 H 0.3966 0.4908 0.0582 0.040 Uiso 1 1 calc R . .
C10 C 0.2728(3) 0.47111(17) 0.30778(12) 0.0348(4) Uani 1 1 d . . .
H10 H 0.2433 0.4673 0.3704 0.042 Uiso 1 1 calc R . .
C9 C 0.4625(3) 0.40887(17) 0.27301(12) 0.0339(4) Uani 1 1 d . . .
H9 H 0.5638 0.3606 0.3127 0.041 Uiso 1 1 calc R . .
C16 C -0.7285(4) 0.8929(2) 0.01851(14) 0.0531(5) Uani 1 1 d . . .
H16A H -0.6206 0.9061 -0.0293 0.080 Uiso 1 1 calc R . .
H16B H -0.8141 0.9740 0.0305 0.080 Uiso 1 1 calc R . .
H16C H -0.8253 0.8362 0.0000 0.080 Uiso 1 1 calc R . .
H1 H -0.027(3) 0.634(2) 0.0608(16) 0.041(6) Uiso 1 1 d . . .
H3 H -0.423(3) 0.743(2) 0.2171(16) 0.042(6) Uiso 1 1 d . . .
O7 O -1.2731(2) 0.94130(14) 0.45515(9) 0.0486(4) Uani 1 1 d . . .
O6 O -1.3649(2) 0.90231(15) 0.59789(9) 0.0470(4) Uani 1 1 d . . .
O4 O -0.3276(2) 0.62175(13) 0.41328(9) 0.0402(3) Uani 1 1 d . . .
O5 O -0.5597(2) 0.75965(13) 0.33162(8) 0.0425(3) Uani 1 1 d . . .
C17 C -0.5120(3) 0.69810(17) 0.40169(12) 0.0343(4) Uani 1 1 d . . .
C18 C -0.6600(3) 0.70363(18) 0.48334(12) 0.0373(4) Uani 1 1 d . . .
H18A H -0.5885 0.7388 0.5314 0.045 Uiso 1 1 calc R . .
H18B H -0.6843 0.6171 0.5047 0.045 Uiso 1 1 calc R . .
C20 C -1.0201(3) 0.80498(19) 0.54822(12) 0.0398(4) Uani 1 1 d . . .
H20A H -1.0525 0.7227 0.5757 0.048 Uiso 1 1 calc R . .
H20B H -0.9393 0.8430 0.5920 0.048 Uiso 1 1 calc R . .
C19 C -0.8782(3) 0.78384(18) 0.46471(12) 0.0366(4) Uani 1 1 d . . .
H19A H -0.9572 0.7424 0.4222 0.044 Uiso 1 1 calc R . .
H19B H -0.8525 0.8666 0.4357 0.044 Uiso 1 1 calc R . .
C21 C -1.2298(3) 0.88921(18) 0.52848(12) 0.0363(4) Uani 1 1 d . . .
H4A H -0.237(4) 0.612(2) 0.3583(19) 0.065(7) Uiso 1 1 d . . .
H6A H -1.487(5) 0.957(3) 0.579(2) 0.081(9) 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
O3 0.0408(7) 0.0510(8) 0.0342(7) -0.0019(6) -0.0083(5) 0.0162(6)
N2 0.0320(7) 0.0356(8) 0.0287(7) 0.0017(6) -0.0017(6) 0.0023(6)
O2 0.0492(8) 0.0615(9) 0.0314(7) 0.0034(6) -0.0001(6) 0.0151(6)
N1 0.0332(7) 0.0362(8) 0.0270(8) 0.0048(6) -0.0019(6) 0.0035(6)
N3 0.0321(7) 0.0376(8) 0.0292(8) 0.0005(6) -0.0007(6) 0.0053(6)
O1 0.0365(6) 0.0454(8) 0.0365(7) 0.0119(6) 0.0033(5) 0.0002(5)
C12 0.0305(8) 0.0287(9) 0.0323(9) 0.0043(7) -0.0020(6) 0.0001(7)
C11 0.0306(8) 0.0303(9) 0.0315(9) 0.0006(7) -0.0008(7) -0.0025(7)
C14 0.0308(8) 0.0273(9) 0.0318(9) 0.0011(7) -0.0021(7) -0.0012(7)
C2 0.0312(8) 0.0399(10) 0.0330(9) 0.0004(7) -0.0021(7) -0.0030(7)
C8 0.0311(8) 0.0308(9) 0.0337(9) 0.0031(7) -0.0027(7) -0.0031(7)
C6 0.0317(8) 0.0363(9) 0.0285(9) 0.0020(7) -0.0005(6) -0.0004(7)
C1 0.0315(8) 0.0333(9) 0.0255(8) 0.0012(7) -0.0034(6) 0.0006(7)
C7 0.0324(8) 0.0350(9) 0.0302(9) 0.0031(7) -0.0038(7) -0.0043(7)
C3 0.0347(9) 0.0424(11) 0.0400(10) -0.0031(8) -0.0076(7) 0.0048(8)
C4 0.0513(11) 0.0345(10) 0.0326(9) 0.0010(7) -0.0068(8) 0.0063(8)
C5 0.0456(10) 0.0361(10) 0.0295(9) 0.0036(7) 0.0009(7) -0.0049(8)
C15 0.0352(9) 0.0339(9) 0.0329(9) -0.0001(7) -0.0018(7) 0.0041(7)
C13 0.0338(9) 0.0334(9) 0.0309(9) 0.0059(7) -0.0011(7) -0.0026(7)
C10 0.0395(9) 0.0367(10) 0.0262(8) 0.0013(7) -0.0029(7) -0.0001(7)
C9 0.0340(9) 0.0340(9) 0.0317(9) 0.0036(7) -0.0061(7) -0.0002(7)
C16 0.0520(11) 0.0598(13) 0.0414(11) -0.0030(10) -0.0181(9) 0.0165(10)
O7 0.0441(7) 0.0622(9) 0.0325(7) 0.0063(6) 0.0049(5) 0.0082(6)
O6 0.0406(7) 0.0615(9) 0.0332(7) 0.0048(6) 0.0082(6) 0.0050(6)
O4 0.0344(6) 0.0473(8) 0.0345(7) 0.0048(6) -0.0010(5) 0.0039(5)
O5 0.0404(7) 0.0476(8) 0.0333(7) 0.0063(6) 0.0035(5) 0.0081(6)
C17 0.0337(9) 0.0344(9) 0.0335(9) 0.0015(7) -0.0026(7) -0.0029(7)
C18 0.0379(9) 0.0405(10) 0.0317(9) 0.0039(7) -0.0006(7) -0.0039(8)
C20 0.0381(9) 0.0460(11) 0.0330(10) 0.0055(8) 0.0024(7) -0.0045(8)
C19 0.0354(9) 0.0399(10) 0.0332(9) -0.0002(7) 0.0011(7) -0.0026(7)
C21 0.0375(9) 0.0397(10) 0.0312(9) -0.0009(8) 0.0033(7) -0.0066(7)

_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
O3 C15 1.336(2) . ?
O3 C16 1.445(2) . ?
N2 C14 1.334(2) . ?
N2 C11 1.392(2) . ?
O2 C15 1.202(2) . ?
N1 C14 1.337(2) . ?
N1 C12 1.390(2) . ?
N1 H1 0.84(2) . ?
N3 C14 1.369(2) . ?
N3 C15 1.370(2) . ?
N3 H3 0.88(2) . ?
O1 C7 1.228(2) . ?
C12 C13 1.376(2) . ?
C12 C11 1.399(2) . ?
C11 C10 1.401(2) . ?
C2 C3 1.387(3) . ?
C2 C1 1.393(2) . ?
C2 H2 0.9500 . ?
C8 C13 1.399(2) . ?
C8 C9 1.405(3) . ?
C8 C7 1.486(2) . ?
C6 C5 1.386(3) . ?
C6 C1 1.395(2) . ?
C6 H6 0.9500 . ?
C1 C7 1.496(2) . ?
C3 C4 1.382(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C13 H13 0.9500 . ?
C10 C9 1.376(3) . ?
C10 H10 0.9500 . ?
C9 H9 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O7 C21 1.214(2) . ?
O6 C21 1.318(2) . ?
O6 H6A 0.92(3) . ?
O4 C17 1.317(2) . ?
O4 H4A 0.99(3) . ?
O5 C17 1.218(2) . ?
C17 C18 1.505(3) . ?
C18 C19 1.519(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C20 C21 1.499(3) . ?
C20 C19 1.520(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 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
C15 O3 C16 116.15(15) . . ?
C14 N2 C11 104.00(14) . . ?
C14 N1 C12 106.71(15) . . ?
C14 N1 H1 124.1(15) . . ?
C12 N1 H1 128.2(15) . . ?
C14 N3 C15 124.02(16) . . ?
C14 N3 H3 116.7(14) . . ?
C15 N3 H3 119.2(14) . . ?
C13 C12 N1 131.52(16) . . ?
C13 C12 C11 123.02(15) . . ?
N1 C12 C11 105.46(14) . . ?
N2 C11 C12 109.79(14) . . ?
N2 C11 C10 130.57(16) . . ?
C12 C11 C10 119.64(16) . . ?
N2 C14 N1 114.02(15) . . ?
N2 C14 N3 121.24(15) . . ?
N1 C14 N3 124.73(16) . . ?
C3 C2 C1 119.51(16) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C13 C8 C9 120.15(16) . . ?
C13 C8 C7 117.46(15) . . ?
C9 C8 C7 122.38(15) . . ?
C5 C6 C1 120.43(16) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C2 C1 C6 119.49(15) . . ?
C2 C1 C7 119.48(15) . . ?
C6 C1 C7 120.53(15) . . ?
O1 C7 C8 120.48(15) . . ?
O1 C7 C1 119.57(16) . . ?
C8 C7 C1 119.84(14) . . ?
C4 C3 C2 120.71(17) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C3 C4 C5 120.09(17) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 119.71(17) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
O2 C15 O3 126.00(16) . . ?
O2 C15 N3 125.64(16) . . ?
O3 C15 N3 108.35(15) . . ?
C12 C13 C8 117.19(16) . . ?
C12 C13 H13 121.4 . . ?
C8 C13 H13 121.4 . . ?
C9 C10 C11 117.78(16) . . ?
C9 C10 H10 121.1 . . ?
C11 C10 H10 121.1 . . ?
C10 C9 C8 122.22(16) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C21 O6 H6A 107.5(18) . . ?
C17 O4 H4A 113.8(15) . . ?
O5 C17 O4 123.53(16) . . ?
O5 C17 C18 122.47(15) . . ?
O4 C17 C18 114.00(15) . . ?
C17 C18 C19 112.17(15) . . ?
C17 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C21 C20 C19 112.25(15) . . ?
C21 C20 H20A 109.2 . . ?
C19 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
C19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C18 C19 C20 113.40(15) . . ?
C18 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
C20 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
O7 C21 O6 122.41(17) . . ?
O7 C21 C20 123.41(16) . . ?
O6 C21 C20 114.18(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.84(2) 2.22(2) 2.7403(19) 120.1(18) .
N1 H1 O1 0.84(2) 2.44(2) 3.079(2) 133.0(18) 2_665
N3 H3 O5 0.88(2) 1.90(2) 2.774(2) 170(2) .
O4 H4A N2 0.99(3) 1.71(3) 2.6902(19) 175(2) .
O6 H6A O7 0.92(3) 1.79(3) 2.7091(19) 178(3) 2_276

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        65.09
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.041