# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Prof. Xuewei Liu'
_publ_contact_author_email       xuewei@ntu.edu.sg

_publ_section_title              
;
Facile synthesis of carbohydrate-integrated
isoxazolines through tandem [4 + 1] cycloaddition and
rearrangement of 2-nitroglycals
;
loop_
_publ_author_name
'Shuting Cai'
'Shaohua Xiang'
'Jing Zeng'
B.Gorityala
'Xuewei Liu'

# Attachment '- liu50.cif'

data_liu50
_database_code_depnum_ccdc_archive 'CCDC 826204'
#TrackingRef '- liu50.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_absolute_configuration unk
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H35 N O7'
_chemical_formula_sum            'C36 H35 N O7'
_chemical_formula_weight         593.65

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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)

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

_cell_length_a                   10.4039(4)
_cell_length_b                   11.4624(4)
_cell_length_c                   12.6741(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.861(2)
_cell_angle_gamma                90.00
_cell_volume                     1510.64(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      32.66

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             628
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9647
_exptl_absorpt_correction_T_max  0.9769
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      103(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            37285
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         33.16
_reflns_number_total             5923
_reflns_number_gt                5241
_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^)+(0.0759P)^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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5923
_refine_ls_number_parameters     472
_refine_ls_number_restraints     264
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1139
_refine_ls_wR_factor_gt          0.1015
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.57996(13) 1.02765(14) 1.02377(11) 0.0137(3) Uani 1 1 d . . .
C2 C 0.51187(13) 0.94566(14) 0.94796(11) 0.0146(3) Uani 1 1 d . . .
H2 H 0.4749 0.8802 0.9893 0.017 Uiso 1 1 calc R . .
C3 C 0.61399(13) 0.89528(14) 0.87587(10) 0.0135(2) Uani 1 1 d . . .
H3 H 0.5752 0.8316 0.8312 0.016 Uiso 1 1 calc R . .
C4 C 0.72435(14) 0.84564(14) 0.94603(11) 0.0146(3) Uani 1 1 d . B .
H4 H 0.6865 0.7890 0.9964 0.018 Uiso 1 1 calc R . .
C5 C 0.69952(14) 0.98308(14) 1.08046(11) 0.0140(2) Uani 1 1 d . B .
H5 H 0.6781 0.9240 1.1353 0.017 Uiso 1 1 calc R . .
C6 C 0.75121(13) 1.09586(14) 1.13125(11) 0.0142(3) Uani 1 1 d . . .
C7 C 0.77718(14) 1.08408(15) 1.25208(11) 0.0165(3) Uani 1 1 d . . .
C8 C 0.80706(14) 1.18879(14) 1.31722(11) 0.0149(3) Uani 1 1 d . . .
C9 C 0.80453(16) 1.17543(16) 1.42732(12) 0.0206(3) Uani 1 1 d . . .
H9 H 0.7819 1.1024 1.4569 0.025 Uiso 1 1 calc R . .
C10 C 0.83496(18) 1.26875(17) 1.49269(12) 0.0231(3) Uani 1 1 d . . .
H10 H 0.8309 1.2594 1.5670 0.028 Uiso 1 1 calc R . .
C11 C 0.87162(15) 1.37659(16) 1.45155(11) 0.0187(3) Uani 1 1 d . . .
C12 C 0.91075(19) 1.47611(18) 1.52289(14) 0.0271(4) Uani 1 1 d . . .
H12A H 0.8380 1.4986 1.5657 0.041 Uiso 1 1 calc R . .
H12B H 0.9368 1.5428 1.4801 0.041 Uiso 1 1 calc R . .
H12C H 0.9830 1.4518 1.5693 0.041 Uiso 1 1 calc R . .
C13 C 0.87114(17) 1.38922(16) 1.34188(12) 0.0216(3) Uani 1 1 d . . .
H13 H 0.8939 1.4622 1.3123 0.026 Uiso 1 1 calc R . .
C14 C 0.83801(16) 1.29685(15) 1.27512(11) 0.0196(3) Uani 1 1 d . . .
H14 H 0.8365 1.3076 1.2008 0.024 Uiso 1 1 calc R . .
C15 C 0.29596(13) 1.00198(16) 0.94601(11) 0.0181(3) Uani 1 1 d . . .
H15A H 0.3128 1.0421 1.0142 0.022 Uiso 1 1 calc R . .
H15B H 0.2666 0.9217 0.9608 0.022 Uiso 1 1 calc R . .
C16 C 0.19377(14) 1.06622(14) 0.88285(11) 0.0155(3) Uani 1 1 d . . .
C17 C 0.06541(14) 1.03400(16) 0.89199(12) 0.0175(3) Uani 1 1 d . . .
H17 H 0.0437 0.9721 0.9379 0.021 Uiso 1 1 calc R . .
C18 C -0.03125(14) 1.09199(16) 0.83423(12) 0.0201(3) Uani 1 1 d . . .
H18 H -0.1186 1.0696 0.8407 0.024 Uiso 1 1 calc R . .
C19 C 0.00047(16) 1.18262(17) 0.76710(12) 0.0226(3) Uani 1 1 d . . .
H19 H -0.0652 1.2217 0.7271 0.027 Uiso 1 1 calc R . .
C20 C 0.12822(17) 1.21634(17) 0.75821(13) 0.0226(3) Uani 1 1 d . . .
H20 H 0.1496 1.2791 0.7130 0.027 Uiso 1 1 calc R . .
C21 C 0.22490(15) 1.15768(16) 0.81591(12) 0.0200(3) Uani 1 1 d . . .
H21 H 0.3122 1.1802 0.8095 0.024 Uiso 1 1 calc R . .
C22 C 0.59971(16) 0.99678(16) 0.70876(12) 0.0199(3) Uani 1 1 d . . .
H22A H 0.6271 1.0711 0.6766 0.024 Uiso 1 1 calc R . .
H22B H 0.5062 1.0020 0.7200 0.024 Uiso 1 1 calc R . .
C23 C 0.62430(15) 0.89831(15) 0.63294(11) 0.0179(3) Uani 1 1 d . . .
C24 C 0.74838(16) 0.87609(17) 0.59944(13) 0.0229(3) Uani 1 1 d . . .
H24 H 0.8183 0.9215 0.6265 0.027 Uiso 1 1 calc R . .
C25 C 0.77042(17) 0.78816(19) 0.52701(13) 0.0267(4) Uani 1 1 d . . .
H25 H 0.8554 0.7733 0.5052 0.032 Uiso 1 1 calc R . .
C26 C 0.66858(19) 0.72181(18) 0.48630(14) 0.0276(4) Uani 1 1 d . . .
H26 H 0.6836 0.6623 0.4360 0.033 Uiso 1 1 calc R . .
C27 C 0.54510(19) 0.7428(2) 0.51950(15) 0.0291(4) Uani 1 1 d . . .
H27 H 0.4754 0.6971 0.4923 0.035 Uiso 1 1 calc R . .
C28 C 0.52276(16) 0.83077(17) 0.59281(13) 0.0236(3) Uani 1 1 d . . .
H28 H 0.4379 0.8446 0.6154 0.028 Uiso 1 1 calc R . .
C29 C 0.82460(14) 0.78140(14) 0.88415(12) 0.0170(3) Uani 1 1 d D . .
H29A H 0.8495 0.8260 0.8212 0.020 Uiso 1 1 calc R A 1
H29B H 0.9023 0.7637 0.9284 0.020 Uiso 1 1 calc R A 1
O7 O 0.7558(18) 0.6788(11) 0.8559(10) 0.0209(19) Uani 0.38(2) 1 d PDU B 1
C30 C 0.8200(15) 0.6104(11) 0.7793(13) 0.018(2) Uani 0.38(2) 1 d PDU B 1
H30A H 0.9092 0.5919 0.8035 0.022 Uiso 0.38(2) 1 calc PR B 1
H30B H 0.8221 0.6514 0.7107 0.022 Uiso 0.38(2) 1 calc PR B 1
C31 C 0.7394(14) 0.5020(10) 0.7712(14) 0.016(2) Uani 0.38(2) 1 d PDU B 1
C32 C 0.7850(16) 0.3976(13) 0.8141(17) 0.025(2) Uani 0.38(2) 1 d PDU B 1
H32 H 0.8704 0.3938 0.8427 0.030 Uiso 0.38(2) 1 calc PR B 1
C33 C 0.7088(14) 0.2999(11) 0.8157(14) 0.037(3) Uani 0.38(2) 1 d PDU B 1
H33 H 0.7403 0.2300 0.8474 0.044 Uiso 0.38(2) 1 calc PR B 1
C34 C 0.5853(14) 0.3038(11) 0.7710(15) 0.038(3) Uani 0.38(2) 1 d PDU B 1
H34 H 0.5310 0.2374 0.7746 0.045 Uiso 0.38(2) 1 calc PR B 1
C35 C 0.5411(11) 0.4033(14) 0.7214(12) 0.032(2) Uani 0.38(2) 1 d PDU B 1
H35 H 0.4572 0.4048 0.6895 0.038 Uiso 0.38(2) 1 calc PR B 1
C36 C 0.6193(14) 0.5023(13) 0.7177(19) 0.028(3) Uani 0.38(2) 1 d PDU B 1
H36 H 0.5912 0.5693 0.6793 0.034 Uiso 0.38(2) 1 calc PR B 1
O7A O 0.7589(10) 0.6826(7) 0.8415(7) 0.0200(11) Uani 0.62(2) 1 d PDU B 2
C30A C 0.8338(8) 0.5967(7) 0.7905(8) 0.0168(13) Uani 0.62(2) 1 d PDU B 2
H30C H 0.9081 0.5731 0.8365 0.020 Uiso 0.62(2) 1 calc PR B 2
H30D H 0.8665 0.6277 0.7235 0.020 Uiso 0.62(2) 1 calc PR B 2
C31A C 0.7456(8) 0.4938(7) 0.7692(9) 0.0188(17) Uani 0.62(2) 1 d PDU B 2
C32A C 0.6296(10) 0.5147(8) 0.7110(12) 0.0243(16) Uani 0.62(2) 1 d PDU B 2
H32A H 0.6122 0.5903 0.6832 0.029 Uiso 0.62(2) 1 calc PR B 2
C33A C 0.5407(7) 0.4252(7) 0.6942(6) 0.0245(11) Uani 0.62(2) 1 d PDU B 2
H33A H 0.4646 0.4380 0.6523 0.029 Uiso 0.62(2) 1 calc PR B 2
C34A C 0.5652(7) 0.3162(7) 0.7398(6) 0.0274(12) Uani 0.62(2) 1 d PDU B 2
H34A H 0.5051 0.2546 0.7288 0.033 Uiso 0.62(2) 1 calc PR B 2
C35A C 0.6762(8) 0.2969(5) 0.8009(5) 0.0222(12) Uani 0.62(2) 1 d PDU B 2
H35A H 0.6915 0.2228 0.8327 0.027 Uiso 0.62(2) 1 calc PR B 2
C36A C 0.7657(9) 0.3872(7) 0.8156(9) 0.0193(12) Uani 0.62(2) 1 d PDU B 2
H36A H 0.8412 0.3744 0.8582 0.023 Uiso 0.62(2) 1 calc PR B 2
N1 N 0.55303(12) 1.13370(13) 1.04156(10) 0.0173(2) Uani 1 1 d . . .
O1 O 0.78712(10) 0.93664(10) 1.00711(8) 0.0158(2) Uani 1 1 d . . .
O2 O 0.86315(11) 1.13706(12) 1.08610(9) 0.0201(2) Uani 1 1 d . . .
H2A H 0.8714 1.1058 1.0268 0.030 Uiso 1 1 calc R . .
O3 O 0.77219(15) 0.98731(12) 1.29154(9) 0.0276(3) Uani 1 1 d . . .
O4 O 0.64787(11) 1.17908(11) 1.11669(9) 0.0187(2) Uani 1 1 d . . .
O5 O 0.41151(10) 0.99818(11) 0.88733(8) 0.0165(2) Uani 1 1 d . . .
O6 O 0.66624(10) 0.98287(11) 0.80990(8) 0.0163(2) 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 0.0132(6) 0.0147(7) 0.0131(5) -0.0010(5) 0.0008(4) -0.0007(5)
C2 0.0126(6) 0.0154(7) 0.0156(6) -0.0019(5) -0.0007(4) -0.0002(5)
C3 0.0147(6) 0.0119(7) 0.0138(5) -0.0020(5) -0.0002(4) -0.0011(5)
C4 0.0155(6) 0.0121(7) 0.0162(6) -0.0037(5) -0.0012(5) -0.0008(5)
C5 0.0149(6) 0.0135(7) 0.0137(5) -0.0028(5) -0.0002(4) 0.0008(5)
C6 0.0143(6) 0.0128(7) 0.0153(6) -0.0022(5) -0.0007(4) 0.0008(5)
C7 0.0178(6) 0.0157(8) 0.0160(6) -0.0019(5) -0.0013(5) 0.0005(5)
C8 0.0173(6) 0.0145(7) 0.0129(5) -0.0009(5) -0.0018(4) 0.0012(5)
C9 0.0283(7) 0.0185(8) 0.0149(6) 0.0006(5) -0.0031(5) 0.0009(6)
C10 0.0328(8) 0.0238(9) 0.0122(6) -0.0011(6) -0.0042(5) 0.0010(7)
C11 0.0190(6) 0.0206(8) 0.0163(6) -0.0053(5) -0.0005(5) 0.0016(6)
C12 0.0357(9) 0.0239(10) 0.0215(7) -0.0104(6) -0.0010(6) -0.0025(7)
C13 0.0304(8) 0.0177(8) 0.0167(6) -0.0027(5) 0.0013(5) -0.0047(6)
C14 0.0277(8) 0.0171(8) 0.0141(6) -0.0017(5) 0.0019(5) -0.0040(6)
C15 0.0118(6) 0.0257(9) 0.0169(6) 0.0026(5) 0.0022(4) 0.0003(5)
C16 0.0133(6) 0.0188(8) 0.0146(6) -0.0023(5) 0.0008(4) -0.0007(5)
C17 0.0139(6) 0.0215(8) 0.0172(6) -0.0022(5) 0.0018(5) -0.0018(5)
C18 0.0151(6) 0.0251(9) 0.0201(6) -0.0015(6) 0.0006(5) 0.0009(6)
C19 0.0227(7) 0.0251(9) 0.0200(6) -0.0004(6) -0.0004(5) 0.0070(6)
C20 0.0277(8) 0.0180(8) 0.0222(7) 0.0023(6) 0.0030(6) 0.0011(6)
C21 0.0181(6) 0.0200(9) 0.0222(7) -0.0007(6) 0.0022(5) -0.0035(6)
C22 0.0245(7) 0.0196(8) 0.0155(6) -0.0001(5) -0.0004(5) 0.0055(6)
C23 0.0204(6) 0.0196(8) 0.0138(5) 0.0014(5) 0.0015(5) 0.0017(6)
C24 0.0204(7) 0.0264(9) 0.0220(7) -0.0029(6) 0.0044(5) -0.0004(6)
C25 0.0267(8) 0.0314(10) 0.0223(7) -0.0014(7) 0.0065(6) 0.0065(7)
C26 0.0375(9) 0.0245(10) 0.0207(7) -0.0065(6) 0.0020(6) 0.0047(7)
C27 0.0307(9) 0.0321(11) 0.0242(8) -0.0059(7) -0.0033(6) -0.0038(8)
C28 0.0202(7) 0.0297(10) 0.0209(7) -0.0022(6) -0.0009(5) 0.0006(6)
C29 0.0167(6) 0.0133(7) 0.0210(6) -0.0050(5) 0.0015(5) -0.0001(5)
O7 0.028(3) 0.013(3) 0.022(3) -0.010(2) 0.014(2) -0.003(2)
C30 0.017(3) 0.011(3) 0.028(4) 0.002(2) 0.002(2) 0.005(3)
C31 0.027(4) 0.009(4) 0.013(4) 0.000(3) 0.007(3) 0.011(3)
C32 0.026(4) 0.017(4) 0.034(4) -0.007(3) 0.014(3) -0.004(3)
C33 0.018(4) 0.027(4) 0.065(6) -0.010(4) 0.008(4) 0.001(3)
C34 0.034(5) 0.019(4) 0.061(7) -0.021(4) 0.018(4) -0.010(3)
C35 0.021(3) 0.034(6) 0.040(5) -0.011(4) 0.001(3) -0.005(3)
C36 0.023(4) 0.030(6) 0.032(4) -0.007(4) -0.001(4) 0.013(4)
O7A 0.0181(18) 0.018(2) 0.024(2) -0.0093(14) 0.0066(16) -0.0041(13)
C30A 0.017(2) 0.010(2) 0.024(2) -0.0075(19) 0.0029(15) 0.0038(17)
C31A 0.018(2) 0.017(3) 0.022(3) -0.011(2) 0.0053(18) -0.005(2)
C32A 0.026(2) 0.014(2) 0.033(3) -0.0047(17) -0.001(2) -0.0071(18)
C33A 0.0215(15) 0.021(2) 0.031(3) -0.0050(18) 0.0019(16) -0.0003(14)
C34A 0.024(2) 0.022(2) 0.036(3) -0.0120(19) 0.0091(18) -0.0048(16)
C35A 0.027(3) 0.0096(15) 0.0308(19) -0.0025(12) 0.0083(19) -0.0060(17)
C36A 0.027(3) 0.013(2) 0.0179(18) -0.0017(14) 0.003(2) 0.0016(17)
N1 0.0172(5) 0.0174(7) 0.0171(5) -0.0023(5) -0.0035(4) -0.0001(5)
O1 0.0144(4) 0.0148(5) 0.0180(4) -0.0066(4) -0.0011(3) 0.0008(4)
O2 0.0218(5) 0.0212(6) 0.0175(5) -0.0063(4) 0.0050(4) -0.0061(4)
O3 0.0462(8) 0.0162(6) 0.0200(5) 0.0019(5) -0.0055(5) -0.0026(6)
O4 0.0208(5) 0.0133(6) 0.0215(5) -0.0053(4) -0.0065(4) 0.0029(4)
O5 0.0116(4) 0.0232(6) 0.0148(4) -0.0005(4) -0.0002(3) 0.0008(4)
O6 0.0178(5) 0.0154(6) 0.0158(4) 0.0003(4) 0.0006(4) -0.0036(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
C1 N1 1.269(2) . ?
C1 C2 1.505(2) . ?
C1 C5 1.505(2) . ?
C2 O5 1.4110(18) . ?
C2 C3 1.536(2) . ?
C2 H2 1.0000 . ?
C3 O6 1.4255(18) . ?
C3 C4 1.538(2) . ?
C3 H3 1.0000 . ?
C4 O1 1.4426(18) . ?
C4 C29 1.516(2) . ?
C4 H4 1.0000 . ?
C5 O1 1.4259(17) . ?
C5 C6 1.534(2) . ?
C5 H5 1.0000 . ?
C6 O2 1.3964(18) . ?
C6 O4 1.4446(19) . ?
C6 C7 1.552(2) . ?
C7 O3 1.219(2) . ?
C7 C8 1.484(2) . ?
C8 C14 1.391(2) . ?
C8 C9 1.405(2) . ?
C9 C10 1.383(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.399(3) . ?
C10 H10 0.9500 . ?
C11 C13 1.397(2) . ?
C11 C12 1.504(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.392(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 O5 1.4347(17) . ?
C15 C16 1.503(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C21 1.393(2) . ?
C16 C17 1.394(2) . ?
C17 C18 1.393(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.392(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.397(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 O6 1.4457(18) . ?
C22 C23 1.510(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C28 1.393(2) . ?
C23 C24 1.395(2) . ?
C24 C25 1.387(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.390(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.386(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.396(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 O7 1.417(7) . ?
C29 O7A 1.421(4) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
O7 C30 1.430(12) . ?
C30 C31 1.501(10) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.392(11) . ?
C31 C36 1.402(10) . ?
C32 C33 1.373(15) . ?
C32 H32 0.9500 . ?
C33 C34 1.388(12) . ?
C33 H33 0.9500 . ?
C34 C35 1.374(13) . ?
C34 H34 0.9500 . ?
C35 C36 1.398(15) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
O7A C30A 1.424(8) . ?
C30A C31A 1.513(6) . ?
C30A H30C 0.9900 . ?
C30A H30D 0.9900 . ?
C31A C36A 1.370(7) . ?
C31A C32A 1.414(7) . ?
C32A C33A 1.394(9) . ?
C32A H32A 0.9500 . ?
C33A C34A 1.396(8) . ?
C33A H33A 0.9500 . ?
C34A C35A 1.388(7) . ?
C34A H34A 0.9500 . ?
C35A C36A 1.401(9) . ?
C35A H35A 0.9500 . ?
C36A H36A 0.9500 . ?
N1 O4 1.4457(16) . ?
O2 H2A 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
N1 C1 C2 127.55(14) . . ?
N1 C1 C5 115.09(13) . . ?
C2 C1 C5 117.21(13) . . ?
O5 C2 C1 113.95(13) . . ?
O5 C2 C3 110.51(11) . . ?
C1 C2 C3 107.11(11) . . ?
O5 C2 H2 108.4 . . ?
C1 C2 H2 108.4 . . ?
C3 C2 H2 108.4 . . ?
O6 C3 C2 111.61(12) . . ?
O6 C3 C4 107.93(11) . . ?
C2 C3 C4 108.23(11) . . ?
O6 C3 H3 109.7 . . ?
C2 C3 H3 109.7 . . ?
C4 C3 H3 109.7 . . ?
O1 C4 C29 108.77(11) . . ?
O1 C4 C3 111.05(12) . . ?
C29 C4 C3 113.18(12) . . ?
O1 C4 H4 107.9 . . ?
C29 C4 H4 107.9 . . ?
C3 C4 H4 107.9 . . ?
O1 C5 C1 110.56(11) . . ?
O1 C5 C6 111.43(12) . . ?
C1 C5 C6 100.79(12) . . ?
O1 C5 H5 111.2 . . ?
C1 C5 H5 111.2 . . ?
C6 C5 H5 111.2 . . ?
O2 C6 O4 110.58(13) . . ?
O2 C6 C5 113.50(12) . . ?
O4 C6 C5 104.69(11) . . ?
O2 C6 C7 108.24(11) . . ?
O4 C6 C7 106.76(11) . . ?
C5 C6 C7 112.84(13) . . ?
O3 C7 C8 121.25(13) . . ?
O3 C7 C6 118.41(14) . . ?
C8 C7 C6 120.34(13) . . ?
C14 C8 C9 119.36(14) . . ?
C14 C8 C7 123.63(13) . . ?
C9 C8 C7 117.00(14) . . ?
C10 C9 C8 119.94(16) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 121.32(14) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C13 C11 C10 118.03(15) . . ?
C13 C11 C12 120.78(16) . . ?
C10 C11 C12 121.19(14) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C11 121.25(16) . . ?
C14 C13 H13 119.4 . . ?
C11 C13 H13 119.4 . . ?
C8 C14 C13 120.01(13) . . ?
C8 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
O5 C15 C16 109.21(12) . . ?
O5 C15 H15A 109.8 . . ?
C16 C15 H15A 109.8 . . ?
O5 C15 H15B 109.8 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
C21 C16 C17 119.48(14) . . ?
C21 C16 C15 121.24(13) . . ?
C17 C16 C15 119.28(14) . . ?
C18 C17 C16 120.47(15) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 119.78(15) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.24(15) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C21 119.81(16) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C16 C21 C20 120.22(14) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
O6 C22 C23 113.31(13) . . ?
O6 C22 H22A 108.9 . . ?
C23 C22 H22A 108.9 . . ?
O6 C22 H22B 108.9 . . ?
C23 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C28 C23 C24 119.06(15) . . ?
C28 C23 C22 120.39(14) . . ?
C24 C23 C22 120.52(15) . . ?
C25 C24 C23 120.55(16) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 120.18(16) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C27 C26 C25 119.70(17) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C26 C27 C28 120.23(18) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C23 C28 C27 120.27(16) . . ?
C23 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
O7 C29 O7A 7.8(8) . . ?
O7 C29 C4 100.6(8) . . ?
O7A C29 C4 104.7(5) . . ?
O7 C29 H29A 111.7 . . ?
O7A C29 H29A 103.9 . . ?
C4 C29 H29A 111.7 . . ?
O7 C29 H29B 111.7 . . ?
O7A C29 H29B 115.2 . . ?
C4 C29 H29B 111.7 . . ?
H29A C29 H29B 109.4 . . ?
C29 O7 C30 112.5(10) . . ?
O7 C30 C31 103.2(11) . . ?
O7 C30 H30A 111.1 . . ?
C31 C30 H30A 111.1 . . ?
O7 C30 H30B 111.1 . . ?
C31 C30 H30B 111.1 . . ?
H30A C30 H30B 109.1 . . ?
C32 C31 C36 118.6(8) . . ?
C32 C31 C30 120.1(9) . . ?
C36 C31 C30 121.3(9) . . ?
C33 C32 C31 121.2(9) . . ?
C33 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
C32 C33 C34 119.7(9) . . ?
C32 C33 H33 120.2 . . ?
C34 C33 H33 120.2 . . ?
C35 C34 C33 120.3(8) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C34 C35 C36 120.2(9) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C35 C36 C31 119.5(9) . . ?
C35 C36 H36 120.3 . . ?
C31 C36 H36 120.3 . . ?
C29 O7A C30A 117.4(7) . . ?
O7A C30A C31A 106.4(6) . . ?
O7A C30A H30C 110.5 . . ?
C31A C30A H30C 110.5 . . ?
O7A C30A H30D 110.5 . . ?
C31A C30A H30D 110.5 . . ?
H30C C30A H30D 108.6 . . ?
C36A C31A C32A 119.4(5) . . ?
C36A C31A C30A 122.4(6) . . ?
C32A C31A C30A 117.6(6) . . ?
C33A C32A C31A 120.4(6) . . ?
C33A C32A H32A 119.8 . . ?
C31A C32A H32A 119.8 . . ?
C32A C33A C34A 119.0(5) . . ?
C32A C33A H33A 120.5 . . ?
C34A C33A H33A 120.5 . . ?
C35A C34A C33A 120.8(5) . . ?
C35A C34A H34A 119.6 . . ?
C33A C34A H34A 119.6 . . ?
C34A C35A C36A 119.6(5) . . ?
C34A C35A H35A 120.2 . . ?
C36A C35A H35A 120.2 . . ?
C31A C36A C35A 120.7(5) . . ?
C31A C36A H36A 119.6 . . ?
C35A C36A H36A 119.6 . . ?
C1 N1 O4 108.16(12) . . ?
C5 O1 C4 109.39(11) . . ?
C6 O2 H2A 109.5 . . ?
C6 O4 N1 109.62(11) . . ?
C2 O5 C15 110.38(11) . . ?
C3 O6 C22 114.64(12) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        33.16
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.147