Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2002

data_1

_database_code_CSD	173804


_journal_coden_Cambridge      182

_publ_requested_journal       'Chemical Communications'

loop_
_publ_author_name
'Shipman, Michael'
'Dransfield, Paul J.'
'Gore, Paul M.'
'Slawin, A.'

_publ_contact_author_name     	'Dr Michael Shipman'  
_publ_contact_author_address 
;
School of Chemistry
University of Exeter
Stocker Road
Exeter
Devon
EX4 4QD
UNITED KINGDOM
;

_publ_contact_author_email       'M.SHIPMAN@EXETER.AC.UK'

_publ_section_title		
;
Divergent Approach to Imino Sugar C-Glycosides using Imino Glycals:
Application to the Stereocontrolled Synthesis of (+)-Deoxoprosophylline
;

_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C16 H25 N O8'
_chemical_formula_sum
'C16 H25 N O8'
_chemical_formula_weight          359.37

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

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

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

_cell_length_a                    8.8915(4)
_cell_length_b                    9.2151(3)
_cell_length_c                    45.8131(19)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      3753.7(3)
_cell_formula_units_Z             8
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     165
_cell_measurement_theta_min       12
_cell_measurement_theta_max       168

_exptl_crystal_description        prism
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           .26
_exptl_crystal_size_mid           .15
_exptl_crystal_size_min           .1
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.272
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1536
_exptl_absorpt_coefficient_mu     0.102
_exptl_absorpt_correction_type    sadabs
_exptl_absorpt_correction_T_min   0.643931
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_process_details    ?

_exptl_special_details
;
disorder at C(28) 75% and 25% split.
;

_diffrn_ambient_temperature       293(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   'CCD area detector'
_diffrn_measurement_method        'phi and omega scans'
_diffrn_detector_area_resol_mean  0.9
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             16307
_diffrn_reflns_av_R_equivalents   0.0510
_diffrn_reflns_av_sigmaI/netI     0.0589
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -50
_diffrn_reflns_limit_l_max        50
_diffrn_reflns_theta_min          2.25
_diffrn_reflns_theta_max          23.43
_reflns_number_total              5410
_reflns_number_gt                 4108
_reflns_threshold_expression      >2sigma(I)

_computing_data_collection        'Bruker SMART'
_computing_cell_refinement        'Bruker SMART'
_computing_data_reduction         'Bruker SHELXTL'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_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^)+(0.0791P)^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      SHELXL
_refine_ls_extinction_coef        0.0044(9)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.2(14)
_refine_ls_number_reflns          5410
_refine_ls_number_parameters      469
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.0748
_refine_ls_R_factor_gt            0.0538
_refine_ls_wR_factor_ref          0.1345
_refine_ls_wR_factor_gt           0.1252
_refine_ls_goodness_of_fit_ref    0.987
_refine_ls_restrained_S_all       0.987
_refine_ls_shift/su_max           0.006
_refine_ls_shift/su_mean          0.001

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 0.2510(4) 0.8549(4) 0.93584(8) 0.0391(8) Uani 1 1 d . . .
H1A H 0.2982 0.8885 0.9177 0.047 Uiso 1 1 calc R . .
C2 C 0.3729(4) 0.7914(4) 0.95516(7) 0.0373(8) Uani 1 1 d . . .
H2A H 0.3296 0.7649 0.9741 0.045 Uiso 1 1 calc R . .
O2 O 0.4869(3) 0.9020(2) 0.95937(5) 0.0418(6) Uani 1 1 d . . .
C3 C 0.4454(4) 0.6590(4) 0.94147(8) 0.0391(8) Uani 1 1 d . . .
H3A H 0.5206 0.6171 0.9547 0.047 Uiso 1 1 calc R . .
O3 O 0.5143(3) 0.7027(3) 0.91424(5) 0.0505(6) Uani 1 1 d . . .
C4 C 0.3236(4) 0.5483(4) 0.93439(8) 0.0400(8) Uani 1 1 d . . .
H4A H 0.2807 0.5113 0.9526 0.048 Uiso 1 1 calc R . .
O4 O 0.3890(3) 0.4292(2) 0.91835(5) 0.0478(6) Uani 1 1 d . . .
C5 C 0.1998(4) 0.6118(4) 0.91608(8) 0.0443(9) Uani 1 1 d . . .
H5A H 0.2413 0.6341 0.8968 0.053 Uiso 1 1 calc R . .
N6 N 0.1401(3) 0.7455(3) 0.92835(7) 0.0450(8) Uani 1 1 d D . .
H6N H 0.082(4) 0.730(5) 0.9463(5) 0.072(13) Uiso 1 1 d D . .
C7 C 0.1737(5) 0.9844(4) 0.95014(9) 0.0560(10) Uani 1 1 d . . .
H7A H 0.2493 1.0520 0.9571 0.067 Uiso 1 1 calc R . .
H7B H 0.1161 0.9513 0.9668 0.067 Uiso 1 1 calc R . .
C8 C 0.0690(6) 1.0623(5) 0.92884(12) 0.0852(15) Uani 1 1 d . . .
H8A H 0.0221 1.1429 0.9385 0.128 Uiso 1 1 calc R . .
H8B H -0.0069 0.9961 0.9222 0.128 Uiso 1 1 calc R . .
H8C H 0.1261 1.0969 0.9125 0.128 Uiso 1 1 calc R . .
C9 C 0.5798(4) 0.8883(4) 0.98216(8) 0.0488(9) Uani 1 1 d . . .
O9 O 0.5667(4) 0.7941(3) 1.00018(6) 0.0690(8) Uani 1 1 d . . .
C10 C 0.6960(6) 1.0031(5) 0.98196(10) 0.0756(14) Uani 1 1 d . . .
H10A H 0.6818 1.0643 0.9652 0.113 Uiso 1 1 calc R . .
H10B H 0.7939 0.9593 0.9811 0.113 Uiso 1 1 calc R . .
H10C H 0.6877 1.0602 0.9994 0.113 Uiso 1 1 calc R . .
C13 C 0.4394(4) 0.3148(4) 0.93355(10) 0.0483(10) Uani 1 1 d . . .
O13 O 0.4357(4) 0.3087(3) 0.95941(7) 0.0702(9) Uani 1 1 d . . .
C11 C 0.6635(5) 0.7359(4) 0.91508(12) 0.0596(12) Uani 1 1 d . . .
O11 O 0.7382(3) 0.7253(4) 0.93647(9) 0.0789(10) Uani 1 1 d . . .
C12 C 0.7144(7) 0.7928(8) 0.88660(12) 0.116(2) Uani 1 1 d . . .
H12A H 0.6324 0.7902 0.8730 0.175 Uiso 1 1 calc R . .
H12B H 0.7955 0.7340 0.8794 0.175 Uiso 1 1 calc R . .
H12C H 0.7483 0.8910 0.8889 0.175 Uiso 1 1 calc R . .
C14 C 0.4986(5) 0.2007(4) 0.91374(10) 0.0589(11) Uani 1 1 d . . .
H14A H 0.4892 0.2324 0.8939 0.088 Uiso 1 1 calc R . .
H14B H 0.4424 0.1128 0.9165 0.088 Uiso 1 1 calc R . .
H14C H 0.6027 0.1832 0.9181 0.088 Uiso 1 1 calc R . .
C15 C 0.0724(5) 0.5066(4) 0.91209(8) 0.0531(10) Uani 1 1 d . . .
H15A H -0.0044 0.5484 0.8996 0.064 Uiso 1 1 calc R . .
H15B H 0.1085 0.4179 0.9031 0.064 Uiso 1 1 calc R . .
O15 O 0.0120(3) 0.4762(3) 0.94037(6) 0.0549(7) Uani 1 1 d . . .
C16 C -0.1297(5) 0.4249(4) 0.94242(11) 0.0579(11) Uani 1 1 d . . .
O16 O -0.1999(4) 0.3957(4) 0.92096(8) 0.0858(11) Uani 1 1 d . . .
C17 C -0.1792(5) 0.4108(6) 0.97238(10) 0.0748(13) Uani 1 1 d . . .
H17A H -0.1003 0.4419 0.9853 0.112 Uiso 1 1 calc R . .
H17B H -0.2035 0.3112 0.9763 0.112 Uiso 1 1 calc R . .
H17C H -0.2667 0.4700 0.9754 0.112 Uiso 1 1 calc R . .
C21 C 0.8308(4) 0.6971(4) 0.80794(9) 0.0518(10) Uani 1 1 d . . .
H21A H 0.7797 0.6518 0.8246 0.062 Uiso 1 1 calc R A 1
C22 C 0.9087(4) 0.5776(4) 0.79064(8) 0.0468(9) Uani 1 1 d . B .
H22A H 0.9479 0.6179 0.7724 0.056 Uiso 1 1 calc R . .
O22 O 0.7958(3) 0.4700(3) 0.78421(6) 0.0536(7) Uani 1 1 d . . .
C23 C 1.0350(4) 0.5079(4) 0.80744(8) 0.0441(9) Uani 1 1 d . . .
H23A H 1.0888 0.4384 0.7951 0.053 Uiso 1 1 calc R B .
O23 O 0.9735(3) 0.4354(3) 0.83282(5) 0.0502(6) Uani 1 1 d . B .
C24 C 1.1416(4) 0.6244(4) 0.81825(8) 0.0439(9) Uani 1 1 d . B .
H24A H 1.1888 0.6715 0.8014 0.053 Uiso 1 1 calc R . .
O24 O 1.2575(3) 0.5620(3) 0.83634(5) 0.0524(7) Uani 1 1 d . . .
C25 C 1.0607(4) 0.7387(4) 0.83628(8) 0.0473(9) Uani 1 1 d . . .
H25A H 1.0175 0.6911 0.8535 0.057 Uiso 1 1 calc R B .
N26 N 0.9380(4) 0.8017(3) 0.81932(7) 0.0515(8) Uani 1 1 d D B .
H26N H 0.967(4) 0.851(3) 0.8012(4) 0.055(11) Uiso 1 1 d D . .
C27 C 0.7126(6) 0.7732(5) 0.78952(14) 0.0879(17) Uani 1 1 d . B 1
H27A H 0.7624 0.8182 0.7730 0.106 Uiso 0.75 1 calc PR B 1
H27B H 0.6442 0.7005 0.7819 0.106 Uiso 0.75 1 calc PR B 1
C28A C 0.6266(8) 0.8809(9) 0.8041(2) 0.111(3) Uani 0.75 1 d P B 1
H28A H 0.5555 0.9226 0.7908 0.167 Uiso 0.75 1 calc PR B 1
H28B H 0.6923 0.9554 0.8113 0.167 Uiso 0.75 1 calc PR B 1
H28C H 0.5737 0.8375 0.8202 0.167 Uiso 0.75 1 calc PR B 1
C28B C 0.738(2) 0.8738(19) 0.7705(3) 0.065(5) Uani 0.25 1 d P C 2
O29 O 0.9218(4) 0.3881(4) 0.74584(7) 0.0840(10) Uani 1 1 d . . .
C29 C 0.8173(5) 0.3794(5) 0.76185(9) 0.0612(11) Uani 1 1 d . B .
C30 C 0.6951(6) 0.2713(7) 0.75988(12) 0.0949(17) Uani 1 1 d . . .
H30A H 0.6244 0.2873 0.7754 0.142 Uiso 1 1 calc R B .
H30B H 0.7366 0.1755 0.7616 0.142 Uiso 1 1 calc R . .
H30C H 0.6450 0.2809 0.7414 0.142 Uiso 1 1 calc R . .
C31 C 0.9499(5) 0.2893(4) 0.83081(10) 0.0573(11) Uani 1 1 d . . .
O31 O 0.9807(4) 0.2232(3) 0.80927(8) 0.0877(11) Uani 1 1 d . B .
C32 C 0.8810(6) 0.2326(5) 0.85768(11) 0.0807(15) Uani 1 1 d . B .
H32A H 0.8694 0.3101 0.8715 0.121 Uiso 1 1 calc R . .
H32B H 0.9445 0.1588 0.8658 0.121 Uiso 1 1 calc R . .
H32C H 0.7843 0.1920 0.8532 0.121 Uiso 1 1 calc R . .
C33 C 1.3796(4) 0.5093(4) 0.82264(10) 0.0519(10) Uani 1 1 d . B .
O33 O 1.3935(3) 0.5123(4) 0.79658(7) 0.0786(9) Uani 1 1 d . . .
C34 C 1.4898(5) 0.4476(5) 0.84364(11) 0.0726(12) Uani 1 1 d . . .
H34A H 1.4524 0.4589 0.8632 0.109 Uiso 1 1 calc R B .
H34B H 1.5840 0.4976 0.8418 0.109 Uiso 1 1 calc R . .
H34C H 1.5041 0.3464 0.8396 0.109 Uiso 1 1 calc R . .
O35 O 1.2204(3) 0.9296(3) 0.82118(6) 0.0623(8) Uani 1 1 d . . .
C35 C 1.1630(5) 0.8572(4) 0.84651(9) 0.0577(11) Uani 1 1 d . B .
H35A H 1.1081 0.9251 0.8587 0.069 Uiso 1 1 calc R . .
H35B H 1.2450 0.8169 0.8579 0.069 Uiso 1 1 calc R . .
C36 C 1.2824(6) 1.0599(6) 0.82471(13) 0.0798(14) Uani 1 1 d . B .
O36 O 1.2974(7) 1.1122(5) 0.84791(11) 0.142(2) Uani 1 1 d . . .
C37 C 1.3204(8) 1.1252(6) 0.79646(12) 0.102(2) Uani 1 1 d . . .
H37A H 1.2963 1.0584 0.7811 0.153 Uiso 1 1 calc R B .
H37B H 1.4260 1.1470 0.7959 0.153 Uiso 1 1 calc R . .
H37C H 1.2638 1.2130 0.7939 0.153 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
C1 0.0360(19) 0.0358(18) 0.046(2) 0.0025(16) 0.0041(17) -0.0022(16)
C2 0.041(2) 0.0340(17) 0.037(2) 0.0069(16) 0.0003(16) -0.0022(17)
O2 0.0428(13) 0.0325(11) 0.0501(14) 0.0038(11) -0.0069(12) -0.0009(11)
C3 0.0360(19) 0.0366(18) 0.045(2) 0.0059(15) -0.0002(17) -0.0018(16)
O3 0.0483(15) 0.0528(14) 0.0504(15) -0.0007(12) 0.0103(13) -0.0081(13)
C4 0.0423(19) 0.0361(18) 0.042(2) 0.0052(16) 0.0023(17) 0.0018(17)
O4 0.0590(16) 0.0359(13) 0.0485(14) -0.0006(12) 0.0018(12) 0.0005(13)
C5 0.050(2) 0.0395(19) 0.043(2) 0.0030(17) -0.0016(18) -0.0079(19)
N6 0.0335(16) 0.0424(17) 0.059(2) 0.0008(15) 0.0002(15) -0.0016(15)
C7 0.054(2) 0.042(2) 0.072(3) 0.004(2) 0.000(2) 0.0041(19)
C8 0.072(3) 0.067(3) 0.117(4) 0.009(3) -0.014(3) 0.033(3)
C9 0.052(2) 0.049(2) 0.046(2) 0.002(2) -0.006(2) 0.000(2)
O9 0.0770(19) 0.0723(19) 0.0577(18) 0.0168(17) -0.0160(16) -0.0027(18)
C10 0.073(3) 0.078(3) 0.075(3) 0.003(2) -0.022(3) -0.020(3)
C13 0.051(2) 0.0329(19) 0.061(3) 0.0071(19) -0.006(2) -0.0117(18)
O13 0.098(2) 0.0534(16) 0.059(2) 0.0151(15) -0.0034(19) 0.0121(17)
C11 0.050(3) 0.050(2) 0.079(3) -0.017(2) 0.019(3) -0.011(2)
O11 0.0406(16) 0.089(2) 0.107(3) -0.015(2) 0.003(2) -0.0017(17)
C12 0.103(4) 0.153(6) 0.094(4) -0.014(4) 0.059(4) -0.035(5)
C14 0.060(2) 0.0358(19) 0.081(3) 0.001(2) 0.000(2) 0.000(2)
C15 0.053(2) 0.052(2) 0.055(2) 0.006(2) -0.005(2) -0.007(2)
O15 0.0414(14) 0.0586(15) 0.0646(17) 0.0110(13) -0.0038(13) -0.0167(14)
C16 0.046(2) 0.047(2) 0.080(3) -0.005(2) -0.004(2) -0.007(2)
O16 0.0612(19) 0.105(3) 0.092(2) -0.029(2) -0.0094(19) -0.025(2)
C17 0.061(3) 0.087(3) 0.076(3) 0.007(3) -0.001(2) -0.017(3)
C21 0.041(2) 0.049(2) 0.065(3) 0.005(2) 0.004(2) 0.001(2)
C22 0.041(2) 0.052(2) 0.048(2) 0.0010(19) 0.0038(18) -0.009(2)
O22 0.0420(14) 0.0623(16) 0.0564(16) -0.0091(14) 0.0065(13) -0.0089(14)
C23 0.042(2) 0.0425(19) 0.048(2) 0.0000(17) 0.0055(18) -0.0057(17)
O23 0.0605(16) 0.0404(13) 0.0497(14) -0.0013(11) 0.0037(13) -0.0054(13)
C24 0.040(2) 0.045(2) 0.046(2) 0.0060(18) -0.0010(17) -0.0006(18)
O24 0.0456(15) 0.0560(15) 0.0557(16) 0.0031(13) -0.0004(13) 0.0007(14)
C25 0.047(2) 0.047(2) 0.048(2) 0.0062(18) 0.0032(19) -0.004(2)
N26 0.0479(19) 0.0431(17) 0.063(2) 0.0071(16) 0.0027(18) 0.0002(17)
C27 0.062(3) 0.064(3) 0.138(5) 0.000(3) -0.037(3) 0.010(3)
C28A 0.077(5) 0.100(6) 0.157(7) -0.024(6) -0.020(5) 0.050(5)
C28B 0.078(12) 0.067(10) 0.051(9) 0.041(9) 0.008(9) 0.011(10)
O29 0.087(2) 0.107(3) 0.0579(18) -0.0200(18) 0.0126(19) -0.011(2)
C29 0.059(3) 0.081(3) 0.043(2) -0.005(2) 0.006(2) 0.002(3)
C30 0.087(4) 0.111(4) 0.087(4) -0.030(3) -0.003(3) -0.033(4)
C31 0.067(3) 0.045(2) 0.060(3) -0.002(2) -0.004(2) 0.001(2)
O31 0.116(3) 0.0531(17) 0.094(3) -0.0117(18) 0.015(2) -0.003(2)
C32 0.102(4) 0.053(2) 0.087(4) 0.017(2) 0.006(3) -0.014(3)
C33 0.039(2) 0.053(2) 0.064(3) 0.003(2) -0.001(2) -0.004(2)
O33 0.0615(19) 0.107(3) 0.068(2) 0.0044(19) 0.0140(16) 0.0231(19)
C34 0.054(2) 0.068(3) 0.095(3) 0.010(3) -0.010(3) 0.006(2)
O35 0.0707(19) 0.0513(16) 0.0648(18) -0.0013(14) 0.0056(15) -0.0142(16)
C35 0.066(3) 0.048(2) 0.060(3) -0.001(2) -0.003(2) -0.003(2)
C36 0.076(3) 0.067(3) 0.097(4) -0.017(3) 0.001(3) -0.025(3)
O36 0.199(5) 0.111(3) 0.116(3) -0.023(3) -0.002(3) -0.093(4)
C37 0.124(5) 0.068(3) 0.114(5) 0.001(3) 0.043(4) -0.041(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 N6 1.452(4) . ?
C1 C2 1.517(5) . ?
C1 C7 1.526(5) . ?
C2 O2 1.450(4) . ?
C2 C3 1.516(5) . ?
O2 C9 1.337(4) . ?
C3 O3 1.447(4) . ?
C3 C4 1.523(5) . ?
O3 C11 1.362(5) . ?
C4 O4 1.443(4) . ?
C4 C5 1.502(5) . ?
O4 C13 1.340(4) . ?
C5 N6 1.454(5) . ?
C5 C15 1.502(5) . ?
C7 C8 1.528(6) . ?
C9 O9 1.204(4) . ?
C9 C10 1.478(6) . ?
C13 O13 1.186(5) . ?
C13 C14 1.486(6) . ?
C11 O11 1.188(6) . ?
C11 C12 1.477(7) . ?
C15 O15 1.430(5) . ?
O15 C16 1.349(5) . ?
C16 O16 1.195(5) . ?
C16 C17 1.447(6) . ?
C21 N26 1.453(5) . ?
C21 C27 1.519(6) . ?
C21 C22 1.523(5) . ?
C22 O22 1.442(4) . ?
C22 C23 1.505(5) . ?
O22 C29 1.335(5) . ?
C23 O23 1.448(4) . ?
C23 C24 1.515(5) . ?
O23 C31 1.365(5) . ?
C24 O24 1.442(4) . ?
C24 C25 1.519(5) . ?
O24 C33 1.345(5) . ?
C25 N26 1.460(5) . ?
C25 C35 1.497(6) . ?
C27 C28A 1.421(9) . ?
O29 C29 1.186(5) . ?
C29 C30 1.476(7) . ?
C31 O31 1.192(5) . ?
C31 C32 1.470(6) . ?
C33 O33 1.201(5) . ?
C33 C34 1.486(6) . ?
O35 C36 1.332(6) . ?
O35 C35 1.432(5) . ?
C36 O36 1.175(6) . ?
C36 C37 1.467(7) . ?

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
N6 C1 C2 110.8(3) . . ?
N6 C1 C7 109.8(3) . . ?
C2 C1 C7 111.9(3) . . ?
O2 C2 C1 107.8(2) . . ?
O2 C2 C3 108.8(3) . . ?
C1 C2 C3 111.9(3) . . ?
C9 O2 C2 118.0(3) . . ?
O3 C3 C2 108.2(3) . . ?
O3 C3 C4 107.7(3) . . ?
C2 C3 C4 108.9(3) . . ?
C11 O3 C3 116.8(3) . . ?
O4 C4 C5 107.9(3) . . ?
O4 C4 C3 109.3(3) . . ?
C5 C4 C3 112.2(3) . . ?
C13 O4 C4 117.9(3) . . ?
N6 C5 C15 108.6(3) . . ?
N6 C5 C4 112.5(3) . . ?
C15 C5 C4 111.6(3) . . ?
C1 N6 C5 115.6(3) . . ?
C1 C7 C8 111.6(4) . . ?
O9 C9 O2 122.9(4) . . ?
O9 C9 C10 126.0(4) . . ?
O2 C9 C10 111.1(3) . . ?
O13 C13 O4 123.2(4) . . ?
O13 C13 C14 125.9(4) . . ?
O4 C13 C14 111.0(4) . . ?
O11 C11 O3 123.3(4) . . ?
O11 C11 C12 125.9(5) . . ?
O3 C11 C12 110.7(5) . . ?
O15 C15 C5 107.4(3) . . ?
C16 O15 C15 118.9(3) . . ?
O16 C16 O15 120.6(4) . . ?
O16 C16 C17 127.0(4) . . ?
O15 C16 C17 112.4(4) . . ?
N26 C21 C27 110.3(3) . . ?
N26 C21 C22 111.6(3) . . ?
C27 C21 C22 111.1(4) . . ?
O22 C22 C23 109.3(3) . . ?
O22 C22 C21 106.7(3) . . ?
C23 C22 C21 112.5(3) . . ?
C29 O22 C22 119.1(3) . . ?
O23 C23 C22 109.0(3) . . ?
O23 C23 C24 107.5(3) . . ?
C22 C23 C24 109.4(3) . . ?
C31 O23 C23 117.3(3) . . ?
O24 C24 C23 110.6(3) . . ?
O24 C24 C25 107.6(3) . . ?
C23 C24 C25 111.9(3) . . ?
C33 O24 C24 116.9(3) . . ?
N26 C25 C35 109.3(3) . . ?
N26 C25 C24 109.9(3) . . ?
C35 C25 C24 112.9(3) . . ?
C21 N26 C25 114.7(3) . . ?
C28A C27 C21 115.7(6) . . ?
O29 C29 O22 123.0(4) . . ?
O29 C29 C30 125.8(4) . . ?
O22 C29 C30 111.3(4) . . ?
O31 C31 O23 121.6(4) . . ?
O31 C31 C32 127.4(4) . . ?
O23 C31 C32 111.0(4) . . ?
O33 C33 O24 122.6(4) . . ?
O33 C33 C34 125.8(4) . . ?
O24 C33 C34 111.6(4) . . ?
C36 O35 C35 118.0(4) . . ?
O35 C35 C25 107.6(3) . . ?
O36 C36 O35 121.8(5) . . ?
O36 C36 C37 127.2(5) . . ?
O35 C36 C37 111.0(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
N6 C1 C2 O2 174.4(3) . . . . ?
C7 C1 C2 O2 -62.7(3) . . . . ?
N6 C1 C2 C3 54.8(4) . . . . ?
C7 C1 C2 C3 177.7(3) . . . . ?
C1 C2 O2 C9 160.0(3) . . . . ?
C3 C2 O2 C9 -78.5(4) . . . . ?
O2 C2 C3 O3 -57.9(3) . . . . ?
C1 C2 C3 O3 61.1(3) . . . . ?
O2 C2 C3 C4 -174.7(2) . . . . ?
C1 C2 C3 C4 -55.7(3) . . . . ?
C2 C3 O3 C11 95.5(4) . . . . ?
C4 C3 O3 C11 -146.9(3) . . . . ?
O3 C3 C4 O4 56.3(3) . . . . ?
C2 C3 C4 O4 173.5(3) . . . . ?
O3 C3 C4 C5 -63.4(4) . . . . ?
C2 C3 C4 C5 53.8(4) . . . . ?
C5 C4 O4 C13 -146.1(3) . . . . ?
C3 C4 O4 C13 91.6(3) . . . . ?
O4 C4 C5 N6 -171.9(3) . . . . ?
C3 C4 C5 N6 -51.3(4) . . . . ?
O4 C4 C5 C15 65.8(4) . . . . ?
C3 C4 C5 C15 -173.6(3) . . . . ?
C2 C1 N6 C5 -52.3(4) . . . . ?
C7 C1 N6 C5 -176.5(3) . . . . ?
C15 C5 N6 C1 175.1(3) . . . . ?
C4 C5 N6 C1 51.1(4) . . . . ?
N6 C1 C7 C8 -65.5(4) . . . . ?
C2 C1 C7 C8 171.0(4) . . . . ?
C2 O2 C9 O9 -4.8(5) . . . . ?
C2 O2 C9 C10 175.6(3) . . . . ?
C4 O4 C13 O13 -1.8(6) . . . . ?
C4 O4 C13 C14 178.3(3) . . . . ?
C3 O3 C11 O11 2.9(6) . . . . ?
C3 O3 C11 C12 -174.1(4) . . . . ?
N6 C5 C15 O15 -62.6(4) . . . . ?
C4 C5 C15 O15 62.0(4) . . . . ?
C5 C15 O15 C16 158.5(3) . . . . ?
C15 O15 C16 O16 5.2(6) . . . . ?
C15 O15 C16 C17 -175.2(4) . . . . ?
N26 C21 C22 O22 171.7(3) . . . . ?
C27 C21 C22 O22 -64.8(4) . . . . ?
N26 C21 C22 C23 51.9(4) . . . . ?
C27 C21 C22 C23 175.4(3) . . . . ?
C23 C22 O22 C29 -80.0(4) . . . . ?
C21 C22 O22 C29 158.1(3) . . . . ?
O22 C22 C23 O23 -54.0(4) . . . . ?
C21 C22 C23 O23 64.2(4) . . . . ?
O22 C22 C23 C24 -171.3(3) . . . . ?
C21 C22 C23 C24 -53.1(4) . . . . ?
C22 C23 O23 C31 98.3(4) . . . . ?
C24 C23 O23 C31 -143.2(3) . . . . ?
O23 C23 C24 O24 57.3(4) . . . . ?
C22 C23 C24 O24 175.6(3) . . . . ?
O23 C23 C24 C25 -62.6(4) . . . . ?
C22 C23 C24 C25 55.6(4) . . . . ?
C23 C24 O24 C33 85.7(4) . . . . ?
C25 C24 O24 C33 -151.8(3) . . . . ?
O24 C24 C25 N26 -177.8(3) . . . . ?
C23 C24 C25 N26 -56.1(4) . . . . ?
O24 C24 C25 C35 59.9(4) . . . . ?
C23 C24 C25 C35 -178.4(3) . . . . ?
C27 C21 N26 C25 -177.3(4) . . . . ?
C22 C21 N26 C25 -53.4(4) . . . . ?
C35 C25 N26 C21 179.7(3) . . . . ?
C24 C25 N26 C21 55.3(4) . . . . ?
N26 C21 C27 C28A -59.5(6) . . . . ?
C22 C21 C27 C28A 176.3(5) . . . . ?
C22 O22 C29 O29 -4.3(6) . . . . ?
C22 O22 C29 C30 176.3(4) . . . . ?
C23 O23 C31 O31 1.3(6) . . . . ?
C23 O23 C31 C32 -177.4(3) . . . . ?
C24 O24 C33 O33 -0.4(6) . . . . ?
C24 O24 C33 C34 -179.7(3) . . . . ?
C36 O35 C35 C25 163.3(4) . . . . ?
N26 C25 C35 O35 -60.0(4) . . . . ?
C24 C25 C35 O35 62.6(4) . . . . ?
C35 O35 C36 O36 3.8(8) . . . . ?
C35 O35 C36 C37 -173.9(4) . . . . ?

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
N6 H6N O9  0.979(5) 2.47(2) 3.359(4) 151(3) 4_467
N26 H26N O29  0.980(5) 2.396(14) 3.331(5) 160(3) 3_756

_diffrn_measured_fraction_theta_max    0.986
_diffrn_reflns_theta_full              23.43
_diffrn_measured_fraction_theta_full   0.986
_refine_diff_density_max    0.179
_refine_diff_density_min   -0.189
_refine_diff_density_rms    0.041