# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ta0611a_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C15 H18 O6), C2 H6 O'
_chemical_formula_sum            'C32 H42 O13'
_chemical_formula_weight         634.67

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   10.1249(7)
_cell_length_b                   4.7655(3)
_cell_length_c                   35.020(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.387(2)
_cell_angle_gamma                90.00
_cell_volume                     1686.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9717
_exptl_absorpt_correction_T_max  0.9772
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_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  'BRUKER CCD AREA DETECTOR'
_diffrn_measurement_method       'PHI-OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13712
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.16
_diffrn_reflns_theta_max         24.03
_reflns_number_total             2655
_reflns_number_gt                1988
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER APEX II'
_computing_cell_refinement       'BRUKER APEX II'
_computing_data_reduction        'BRUKER APEX II'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'MERCURY 2.3, PLATON'
_computing_publication_material  'MERCURY 2.3, PLATON'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1735P)²+1.9664P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.042(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2655
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0858
_refine_ls_wR_factor_ref         0.2743
_refine_ls_wR_factor_gt          0.2555
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.2307(3) 1.0051(6) 0.17813(11) 0.0505(10) Uani 1 1 d . . .
O2 O 1.3182(3) 0.6737(7) 0.21605(9) 0.0439(9) Uani 1 1 d . . .
H2 H 1.3867 0.7582 0.2122 0.066 Uiso 1 1 calc R . .
O3 O 0.8807(4) 0.7172(8) 0.00441(9) 0.0624(11) Uani 1 1 d . . .
H3 H 0.9110 0.8267 -0.0109 0.094 Uiso 1 1 calc R . .
O4 O 0.9958(4) 0.9796(7) 0.04640(8) 0.0517(10) Uani 1 1 d . . .
O5 O 0.5447(3) 0.9374(7) 0.20060(9) 0.0499(10) Uani 1 1 d . . .
O6 O 0.4537(3) 1.2550(7) 0.16162(11) 0.0553(11) Uani 1 1 d . . .
H6 H 0.3853 1.1929 0.1698 0.083 Uiso 1 1 calc R . .
O7A O 0.5084(12) 0.461(3) 0.0157(4) 0.041(3) Uiso 0.25 1 d P . .
O7B O 0.496(2) 0.425(5) 0.0376(7) 0.102(6) Uiso 0.25 1 d P . .
C1 C 1.2186(4) 0.7936(8) 0.19658(11) 0.0301(10) Uani 1 1 d . . .
C2 C 1.0896(4) 0.6415(8) 0.19940(11) 0.0302(10) Uani 1 1 d . . .
H2A H 1.0620 0.6582 0.2254 0.036 Uiso 1 1 calc R . .
H2B H 1.1033 0.4438 0.1943 0.036 Uiso 1 1 calc R . .
C3 C 0.9796(4) 0.7490(8) 0.17212(11) 0.0274(9) Uani 1 1 d . . .
C4 C 0.9737(4) 0.6550(8) 0.13415(11) 0.0284(9) Uani 1 1 d . . .
C5 C 1.0784(4) 0.4624(9) 0.12051(13) 0.0408(11) Uani 1 1 d . . .
H5A H 1.0541 0.2713 0.1252 0.061 Uiso 1 1 calc R . .
H5B H 1.1614 0.5033 0.1340 0.061 Uiso 1 1 calc R . .
H5C H 1.0865 0.4894 0.0936 0.061 Uiso 1 1 calc R . .
C6 C 0.8689(4) 0.7398(8) 0.10906(11) 0.0301(10) Uani 1 1 d . . .
C7 C 0.8545(4) 0.6209(9) 0.06884(11) 0.0371(11) Uani 1 1 d . . .
H7A H 0.8931 0.4345 0.0690 0.045 Uiso 1 1 calc R . .
H7B H 0.7611 0.6019 0.0615 0.045 Uiso 1 1 calc R . .
C8 C 0.9179(4) 0.7933(9) 0.03919(12) 0.0349(10) Uani 1 1 d . . .
C9 C 0.7751(4) 0.9323(8) 0.12079(11) 0.0292(10) Uani 1 1 d . . .
C10 C 0.6621(4) 1.0229(10) 0.09326(13) 0.0432(12) Uani 1 1 d . . .
H10A H 0.5927 0.8857 0.0932 0.065 Uiso 1 1 calc R . .
H10B H 0.6933 1.0393 0.0680 0.065 Uiso 1 1 calc R . .
H10C H 0.6289 1.2010 0.1012 0.065 Uiso 1 1 calc R . .
C11 C 0.7851(3) 1.0365(8) 0.15806(11) 0.0265(9) Uani 1 1 d . . .
C12 C 0.6865(4) 1.2570(8) 0.17006(12) 0.0330(10) Uani 1 1 d . . .
H12A H 0.7237 1.3552 0.1925 0.040 Uiso 1 1 calc R . .
H12B H 0.6727 1.3933 0.1496 0.040 Uiso 1 1 calc R . .
C13 C 0.5549(4) 1.1329(9) 0.17904(11) 0.0305(10) Uani 1 1 d . . .
C14 C 0.8850(3) 0.9397(8) 0.18443(10) 0.0270(9) Uani 1 1 d . . .
C15 C 0.8886(4) 1.0403(10) 0.22533(12) 0.0397(11) Uani 1 1 d . . .
H15A H 0.9593 0.9482 0.2399 0.060 Uiso 1 1 calc R . .
H15B H 0.8059 0.9972 0.2361 0.060 Uiso 1 1 calc R . .
H15C H 0.9027 1.2395 0.2260 0.060 Uiso 1 1 calc R . .
C16A C 0.352(2) 0.586(5) 0.0579(6) 0.061(5) Uiso 0.25 1 d P . .
C16B C 0.351(2) 0.761(4) 0.0241(6) 0.049(5) Uiso 0.25 1 d P . .
C17 C 0.4234(12) 0.594(3) 0.0210(3) 0.061(3) Uiso 0.50 1 d P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.208(5) . ?
O2 C1 1.314(5) . ?
O3 C8 1.305(5) . ?
O4 C8 1.205(5) . ?
O5 C13 1.208(5) . ?
O6 C13 1.299(5) . ?
O7A O7B 0.80(2) . ?
O7A C17 1.091(15) . ?
O7A O7A 1.16(3) 3_665 ?
O7A C17 1.516(18) 3_665 ?
O7B C17 1.21(2) . ?
O7B C16A 1.82(3) . ?
C1 C2 1.502(5) . ?
C2 C3 1.513(5) . ?
C3 C4 1.401(5) . ?
C3 C14 1.406(5) . ?
C4 C6 1.397(5) . ?
C4 C5 1.501(6) . ?
C6 C9 1.399(6) . ?
C6 C7 1.517(5) . ?
C7 C8 1.498(6) . ?
C9 C11 1.395(5) . ?
C9 C10 1.515(5) . ?
C11 C14 1.407(5) . ?
C11 C12 1.526(5) . ?
C12 C13 1.508(6) . ?
C14 C15 1.509(5) . ?
C16A C16B 1.45(3) . ?
C16A C17 1.51(3) . ?
C16B C17 1.09(2) . ?
C17 O7A 1.516(18) 3_665 ?

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
O7B O7A C17 78(2) . . ?
O7B O7A O7A 161(3) . 3_665 ?
C17 O7A O7A 84.6(15) . 3_665 ?
O7B O7A C17 151(2) . 3_665 ?
C17 O7A C17 130.3(12) . 3_665 ?
O7A O7A C17 45.8(10) 3_665 3_665 ?
O7A O7B C17 61.9(19) . . ?
O7A O7B C16A 117(3) . . ?
C17 O7B C16A 55.6(13) . . ?
O1 C1 O2 122.8(4) . . ?
O1 C1 C2 123.7(3) . . ?
O2 C1 C2 113.6(3) . . ?
C1 C2 C3 113.9(3) . . ?
C4 C3 C14 120.4(3) . . ?
C4 C3 C2 118.7(3) . . ?
C14 C3 C2 120.9(3) . . ?
C6 C4 C3 119.5(4) . . ?
C6 C4 C5 120.1(4) . . ?
C3 C4 C5 120.4(4) . . ?
C4 C6 C9 120.6(3) . . ?
C4 C6 C7 120.3(4) . . ?
C9 C6 C7 119.2(4) . . ?
C8 C7 C6 114.7(3) . . ?
O4 C8 O3 123.3(4) . . ?
O4 C8 C7 124.1(4) . . ?
O3 C8 C7 112.5(4) . . ?
C11 C9 C6 119.7(3) . . ?
C11 C9 C10 120.3(4) . . ?
C6 C9 C10 120.0(4) . . ?
C9 C11 C14 120.5(4) . . ?
C9 C11 C12 119.4(3) . . ?
C14 C11 C12 120.1(3) . . ?
C13 C12 C11 112.8(3) . . ?
O5 C13 O6 123.0(4) . . ?
O5 C13 C12 122.8(3) . . ?
O6 C13 C12 114.1(3) . . ?
C3 C14 C11 119.1(3) . . ?
C3 C14 C15 121.2(3) . . ?
C11 C14 C15 119.6(4) . . ?
C16B C16A O7B 83.8(15) . . ?
C17 C16B C16A 71.8(16) . . ?
O7A C17 C16B 168.1(17) . . ?
C16B C17 O7B 146(2) . . ?
O7A C17 C16A 123.5(14) . . ?
C16B C17 C16A 65.0(15) . . ?
O7B C17 C16A 83.2(16) . . ?
O7A C17 O7A 49.7(12) . 3_665 ?
C16B C17 O7A 123.4(15) . 3_665 ?
O7B C17 O7A 89.9(17) . 3_665 ?
C16A C17 O7A 168.7(14) . 3_665 ?

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
O2 H2 O5 0.82 1.88 2.698(4) 176.2 1_655
O3 H3 O4 0.82 1.85 2.661(5) 168.8 3_775

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        24.03
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.201
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.142
# start Validation Reply Form
_vrf_DIFMX01_ta0611a_0m          
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00
RESPONSE: This could be due to the presence of disordered ethanol
molecule and smeared uninterpretable electron densities 
(1.20 e/angstrom cube, 0.85 angstrom away from C16B) observed in the e-map.
;
_vrf_THETM01_ta0611a_0m          
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: The crystal was poorly diffracting at higher Bragg angles 
and this problem could not be resolved even after collecting fresh data set on 
several crystals.
;
_vrf_PLAT097_ta0611a_0m          
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.20 eA-3  
RESPONSE: This could be due to the presence of disordered ethanol
molecule and smeared uninterpretable electron densities (1.20 e/angstrom cube)
 observed in the e-map.
;
_database_code_depnum_ccdc_archive 'CCDC 929277'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ta0668a_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H24 O6'
_chemical_formula_sum            'C18 H24 O6'
_chemical_formula_weight         336.37

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.125(6)
_cell_length_b                   4.993(3)
_cell_length_c                   37.33(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.079(15)
_cell_angle_gamma                90.00
_cell_volume                     1884(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9756
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_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  'BRUKER CCD AREA DETECTOR'
_diffrn_measurement_method       'PHI-OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7322
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.09
_diffrn_reflns_theta_max         17.50
_reflns_number_total             1192
_reflns_number_gt                917
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER APEX II'
_computing_cell_refinement       'BRUKER APEX II'
_computing_data_reduction        'BRUKER APEX II'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'MERCURY 2.3, PLATON'
_computing_publication_material  'MERCURY 2.3, PLATON'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.049(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1192
_refine_ls_number_parameters     224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0792
_refine_ls_wR_factor_ref         0.2647
_refine_ls_wR_factor_gt          0.2436
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4995(7) 0.5005(15) 0.04358(15) 0.082(2) Uani 1 1 d . . .
O2 O 0.3895(7) 0.2249(13) 0.00756(19) 0.100(2) Uani 1 1 d . . .
H2 H 0.4352 0.2935 -0.0074 0.150 Uiso 1 1 calc R . .
O3 O 0.0040(6) 0.7808(11) 0.16032(16) 0.072(2) Uani 1 1 d . . .
H3 H -0.0479 0.6870 0.1483 0.108 Uiso 1 1 calc R . .
O4 O 0.0896(5) 0.4293(15) 0.19004(16) 0.067(2) Uani 1 1 d . . .
O5 O 0.8599(6) 0.2007(12) 0.20392(17) 0.080(2) Uani 1 1 d . . .
H5 H 0.9241 0.3008 0.2054 0.119 Uiso 1 1 calc R . .
O6 O 0.7759(5) 0.5272(14) 0.17056(18) 0.080(2) Uani 1 1 d . . .
C1 C 0.4294(10) 0.310(2) 0.0398(3) 0.060(3) Uani 1 1 d . . .
C2 C 0.3769(7) 0.1354(16) 0.0681(2) 0.055(3) Uani 1 1 d . . .
H2A H 0.4181 -0.0395 0.0669 0.066 Uiso 1 1 calc R . .
H2B H 0.2825 0.1118 0.0632 0.066 Uiso 1 1 calc R . .
C3 C 0.4001(10) 0.2444(18) 0.1055(2) 0.045(2) Uani 1 1 d . . .
C4 C 0.5047(9) 0.1558(16) 0.1270(3) 0.045(2) Uani 1 1 d . . .
C5 C 0.5984(9) -0.0515(17) 0.1141(2) 0.067(3) Uani 1 1 d . . .
H5A H 0.5497 -0.1712 0.0977 0.081 Uiso 1 1 calc R . .
H5B H 0.6313 -0.1570 0.1345 0.081 Uiso 1 1 calc R . .
C6 C 0.7150(9) 0.060(2) 0.0954(2) 0.098(3) Uani 1 1 d . . .
H6A H 0.6840 0.1765 0.0763 0.147 Uiso 1 1 calc R . .
H6B H 0.7643 -0.0850 0.0856 0.147 Uiso 1 1 calc R . .
H6C H 0.7709 0.1581 0.1123 0.147 Uiso 1 1 calc R . .
C7 C 0.5248(8) 0.2579(17) 0.1623(3) 0.046(2) Uani 1 1 d . . .
C8 C 0.6381(8) 0.1583(16) 0.18675(19) 0.051(2) Uani 1 1 d . . .
H8A H 0.6097 0.1558 0.2112 0.062 Uiso 1 1 calc R . .
H8B H 0.6578 -0.0248 0.1802 0.062 Uiso 1 1 calc R . .
C9 C 0.7621(8) 0.320(2) 0.1859(2) 0.050(2) Uani 1 1 d . . .
C10 C 0.4378(10) 0.4546(18) 0.1745(2) 0.043(2) Uani 1 1 d . . .
C11 C 0.4598(7) 0.5672(15) 0.2121(2) 0.054(2) Uani 1 1 d . . .
H11A H 0.5537 0.5658 0.2187 0.065 Uiso 1 1 calc R . .
H11B H 0.4300 0.7519 0.2122 0.065 Uiso 1 1 calc R . .
C12 C 0.3878(8) 0.4114(18) 0.2394(2) 0.072(3) Uani 1 1 d . . .
H12A H 0.2957 0.4009 0.2320 0.109 Uiso 1 1 calc R . .
H12B H 0.3978 0.4997 0.2622 0.109 Uiso 1 1 calc R . .
H12C H 0.4241 0.2341 0.2414 0.109 Uiso 1 1 calc R . .
C13 C 0.3300(8) 0.5391(16) 0.1522(3) 0.047(2) Uani 1 1 d . . .
C14 C 0.2349(8) 0.7514(15) 0.1656(2) 0.054(2) Uani 1 1 d . . .
H14A H 0.2735 0.8325 0.1873 0.064 Uiso 1 1 calc R . .
H14B H 0.2227 0.8911 0.1476 0.064 Uiso 1 1 calc R . .
C15 C 0.1032(9) 0.633(2) 0.1731(2) 0.054(3) Uani 1 1 d . . .
C16 C 0.3112(8) 0.4311(18) 0.1177(3) 0.043(2) Uani 1 1 d . . .
C17 C 0.1944(8) 0.5214(16) 0.0942(2) 0.059(3) Uani 1 1 d . . .
H17A H 0.2213 0.5338 0.0697 0.071 Uiso 1 1 calc R . .
H17B H 0.1695 0.6998 0.1016 0.071 Uiso 1 1 calc R . .
C18 C 0.0726(8) 0.3398(17) 0.0948(2) 0.076(3) Uani 1 1 d . . .
H18A H 0.0862 0.1838 0.0804 0.113 Uiso 1 1 calc R . .
H18B H -0.0037 0.4354 0.0853 0.113 Uiso 1 1 calc R . .
H18C H 0.0590 0.2865 0.1190 0.113 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.192(10) . ?
O2 C1 1.317(10) . ?
O3 C15 1.313(9) . ?
O4 C15 1.211(9) . ?
O5 C9 1.309(9) . ?
O6 C9 1.196(9) . ?
C1 C2 1.490(12) . ?
C2 C3 1.506(10) . ?
C3 C4 1.366(10) . ?
C3 C16 1.389(10) . ?
C4 C7 1.419(10) . ?
C4 C5 1.501(10) . ?
C5 C6 1.509(11) . ?
C7 C10 1.411(10) . ?
C7 C8 1.511(10) . ?
C8 C9 1.494(11) . ?
C10 C13 1.403(10) . ?
C10 C11 1.515(10) . ?
C11 C12 1.502(9) . ?
C13 C16 1.398(10) . ?
C13 C14 1.534(10) . ?
C14 C15 1.498(11) . ?
C16 C17 1.504(10) . ?
C17 C18 1.532(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 121.1(9) . . ?
O1 C1 C2 128.0(8) . . ?
O2 C1 C2 110.9(10) . . ?
C1 C2 C3 113.8(7) . . ?
C4 C3 C16 121.4(7) . . ?
C4 C3 C2 120.3(9) . . ?
C16 C3 C2 118.3(9) . . ?
C3 C4 C7 119.8(7) . . ?
C3 C4 C5 121.2(9) . . ?
C7 C4 C5 119.0(9) . . ?
C4 C5 C6 114.8(7) . . ?
C10 C7 C4 119.3(7) . . ?
C10 C7 C8 120.1(9) . . ?
C4 C7 C8 120.6(9) . . ?
C9 C8 C7 114.9(7) . . ?
O6 C9 O5 122.3(8) . . ?
O6 C9 C8 126.7(9) . . ?
O5 C9 C8 111.0(9) . . ?
C13 C10 C7 119.7(7) . . ?
C13 C10 C11 120.7(9) . . ?
C7 C10 C11 119.6(9) . . ?
C12 C11 C10 112.5(6) . . ?
C16 C13 C10 119.7(7) . . ?
C16 C13 C14 120.7(9) . . ?
C10 C13 C14 119.7(9) . . ?
C15 C14 C13 111.7(6) . . ?
O4 C15 O3 123.7(8) . . ?
O4 C15 C14 123.8(8) . . ?
O3 C15 C14 112.5(9) . . ?
C3 C16 C13 120.1(7) . . ?
C3 C16 C17 120.9(9) . . ?
C13 C16 C17 119.0(9) . . ?
C16 C17 C18 115.0(6) . . ?

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
O5 H5 O4 0.82 1.91 2.667(8) 152.9 1_655
O3 H3 O6 0.82 2.16 2.679(8) 121.2 1_455
O2 H2 O1 0.82 1.85 2.649(9) 165.6 3_665

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        17.50
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.821
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.120
# start Validation Reply Form
_vrf_REFNR01_ta0668a_0m          
;
PROBLEM: Ratio of reflections to parameters is < 6 for a
RESPONSE: The crystal was poorly diffracting at higher Bragg angles and 
the problem could not be resolved even after collecting fresh data set
on several crystals.
;
_vrf_THETM01_ta0668a_0m          
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The crystal was poorly diffracting at higher Bragg angles and 
the problem could not be resolved even after collecting fresh data set
on several crystals.
;
_vrf_DIFMX01_ta0668a_0m          
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00
RESPONSE: We were not able to find out suitable model for the smeared 
electron densities (0.82 e/angstrom cube 3.25 angstrom
away from H18A) present in the e-map.
;
_vrf_PLAT088_ta0668a_0m          
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.35       
RESPONSE: The crystal was poorly diffracting at higher Bragg angles and 
the problem could not be resolved even after collecting fresh data sets
on several crystals.
;
_vrf_PLAT097_ta0668a_0m          
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.82 eA-3  
RESPONSE: We were not able to find out suitable model for the smeared 
electron densities (0.82 e/angstrom cube 3.25 angstrom
 away from H18A) present in the e-map.
;
_vrf_PLAT340_ta0668a_0m          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0124 Ang.  
RESPONSE: The crystal was poorly diffracting and the problem could not be 
resolved even after collecting fresh data  set on several crystals at low 
temparature.
;
_vrf_PLAT410_ta0668a_0m          
;
PROBLEM: Short Intra H...H Contact  H2A    ..  H5A     ..       1.83 Ang.  
RESPONSE: We could not get rid of this problems even after locating the
hydrogen atoms in the e-map. We do believe that the short intra H...H contact 
may be due to the conformation of various arms in the molecule.    
;
_vrf_PLAT601_ta0668a_0m          
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        128 Ang3  
RESPONSE: This could be due to the presence of uninterpretable smeared electron 
densities in the e-map.  
;
_database_code_depnum_ccdc_archive 'CCDC 929278'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ta1175_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H23 O6, C6 H16 N'
_chemical_formula_sum            'C24 H39 N O6'
_chemical_formula_weight         437.56

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

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   30.0728(8)
_cell_length_b                   9.9777(3)
_cell_length_c                   16.8414(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.730(2)
_cell_angle_gamma                90.00
_cell_volume                     4864.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1904
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9693
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 CCD AREA DETECTOR'
_diffrn_measurement_method       'PHI-OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            71057
_diffrn_reflns_av_R_equivalents  0.1044
_diffrn_reflns_av_sigmaI/netI    0.0800
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         0.70
_diffrn_reflns_theta_max         24.96
_reflns_number_total             8471
_reflns_number_gt                5544
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER APEX II'
_computing_cell_refinement       'BRUKER APEX II'
_computing_data_reduction        'BRUKER APEX II'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'MERCURY 2.3, PLATON'
_computing_publication_material  'MERCURY 2.3, PLATON'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0853P)²+28.5407P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.0047(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8471
_refine_ls_number_parameters     574
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1579
_refine_ls_R_factor_gt           0.1053
_refine_ls_wR_factor_ref         0.2727
_refine_ls_wR_factor_gt          0.2468
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.13539(14) -0.1176(5) 0.5096(2) 0.0345(11) Uani 1 1 d . . .
O2 O 0.18391(13) 0.0313(4) 0.5851(2) 0.0251(9) Uani 1 1 d . . .
H2 H 0.1655 0.0298 0.6133 0.038 Uiso 1 1 calc R . .
O3 O 0.05071(12) -0.1689(4) 0.1839(2) 0.0217(9) Uani 1 1 d . . .
O4 O 0.06220(12) -0.3788(4) 0.1597(2) 0.0220(9) Uani 1 1 d . . .
H4 H 0.0841 -0.4290 0.1618 0.033 Uiso 1 1 calc R . .
O5 O 0.12658(13) 0.4535(4) 0.1745(2) 0.0203(9) Uani 1 1 d . . .
O6 O 0.09366(14) 0.3164(4) 0.2448(3) 0.0351(11) Uani 1 1 d . . .
N1 N 0.04861(19) 0.0762(6) 0.2594(3) 0.0421(15) Uani 1 1 d . . .
H1A H 0.0591 0.0024 0.2397 0.051 Uiso 1 1 calc R . .
H1B H 0.0675 0.1445 0.2559 0.051 Uiso 1 1 calc R . .
C1 C 0.17035(18) -0.0529(5) 0.5233(3) 0.0184(12) Uani 1 1 d . . .
C2 C 0.20435(18) -0.0610(6) 0.4709(3) 0.0192(12) Uani 1 1 d . . .
H2A H 0.2290 0.0030 0.4919 0.023 Uiso 1 1 calc R . .
H2B H 0.2180 -0.1498 0.4768 0.023 Uiso 1 1 calc R . .
C3 C 0.18286(17) -0.0331(5) 0.3799(3) 0.0137(11) Uani 1 1 d . . .
C4 C 0.16442(17) -0.1406(5) 0.3254(3) 0.0126(11) Uani 1 1 d . . .
C5 C 0.16332(19) -0.2817(5) 0.3595(3) 0.0181(12) Uani 1 1 d . . .
H5A H 0.1369 -0.3291 0.3252 0.022 Uiso 1 1 calc R . .
H5B H 0.1593 -0.2756 0.4146 0.022 Uiso 1 1 calc R . .
C6 C 0.2070(2) -0.3623(6) 0.3632(4) 0.0294(14) Uani 1 1 d . . .
H6A H 0.2102 -0.3737 0.3084 0.044 Uiso 1 1 calc R . .
H6B H 0.2048 -0.4485 0.3871 0.044 Uiso 1 1 calc R . .
H6C H 0.2334 -0.3153 0.3963 0.044 Uiso 1 1 calc R . .
C7 C 0.14746(17) -0.1145(5) 0.2413(3) 0.0143(11) Uani 1 1 d . . .
C8 C 0.12764(18) -0.2300(5) 0.1836(3) 0.0164(12) Uani 1 1 d . . .
H8A H 0.1311 -0.2100 0.1292 0.020 Uiso 1 1 calc R . .
H8B H 0.1453 -0.3104 0.2033 0.020 Uiso 1 1 calc R . .
C9 C 0.07729(18) -0.2567(5) 0.1767(3) 0.0161(12) Uani 1 1 d . . .
C10 C 0.14815(17) 0.0174(5) 0.2104(3) 0.0158(11) Uani 1 1 d . . .
C11 C 0.1286(2) 0.0460(6) 0.1196(3) 0.0258(13) Uani 1 1 d . . .
H11A H 0.1169 0.1371 0.1133 0.031 Uiso 1 1 calc R . .
H11B H 0.1026 -0.0135 0.0979 0.031 Uiso 1 1 calc R . .
C12 C 0.1628(2) 0.0297(7) 0.0675(4) 0.0357(16) Uani 1 1 d . . .
H12A H 0.1900 0.0815 0.0914 0.053 Uiso 1 1 calc R . .
H12B H 0.1488 0.0604 0.0124 0.053 Uiso 1 1 calc R . .
H12C H 0.1710 -0.0631 0.0662 0.053 Uiso 1 1 calc R . .
C13 C 0.16615(17) 0.1211(5) 0.2648(3) 0.0145(11) Uani 1 1 d . . .
C14 C 0.16932(18) 0.2609(5) 0.2314(3) 0.0167(12) Uani 1 1 d . . .
H14A H 0.1774 0.2529 0.1796 0.020 Uiso 1 1 calc R . .
H14B H 0.1944 0.3079 0.2697 0.020 Uiso 1 1 calc R . .
C15 C 0.12585(18) 0.3470(5) 0.2167(3) 0.0183(12) Uani 1 1 d . . .
C16 C 0.18190(16) 0.0980(5) 0.3499(3) 0.0139(11) Uani 1 1 d . . .
C17 C 0.19653(18) 0.2134(5) 0.4101(3) 0.0178(12) Uani 1 1 d . . .
H17A H 0.1902 0.1893 0.4618 0.021 Uiso 1 1 calc R . .
H17B H 0.1777 0.2910 0.3883 0.021 Uiso 1 1 calc R . .
C18 C 0.24755(19) 0.2529(6) 0.4279(4) 0.0237(13) Uani 1 1 d . . .
H18A H 0.2666 0.1781 0.4519 0.036 Uiso 1 1 calc R . .
H18B H 0.2538 0.3271 0.4656 0.036 Uiso 1 1 calc R . .
H18C H 0.2542 0.2781 0.3773 0.036 Uiso 1 1 calc R . .
C19 C 0.0508(2) 0.0539(6) 0.3474(3) 0.0254(13) Uani 1 1 d . . .
H19A H 0.0222 0.0110 0.3499 0.030 Uiso 1 1 calc R . .
H19B H 0.0757 -0.0087 0.3700 0.030 Uiso 1 1 calc R . .
C20 C 0.0578(3) 0.1710(9) 0.4006(5) 0.060(2) Uani 1 1 d D . .
H20A H 0.0894 0.2002 0.4088 0.072 Uiso 1 1 calc R . .
H20B H 0.0381 0.2419 0.3708 0.072 Uiso 1 1 calc R . .
C21 C 0.0494(3) 0.1605(10) 0.4812(4) 0.066(3) Uani 1 1 d D . .
H21A H 0.0186 0.1282 0.4752 0.098 Uiso 1 1 calc R . .
H21B H 0.0529 0.2471 0.5070 0.098 Uiso 1 1 calc R . .
H21C H 0.0712 0.0992 0.5147 0.098 Uiso 1 1 calc R . .
C22 C 0.00129(19) 0.1069(6) 0.2065(3) 0.0222(13) Uani 1 1 d . . .
H22A H -0.0186 0.0306 0.2070 0.027 Uiso 1 1 calc R . .
H22B H -0.0110 0.1826 0.2299 0.027 Uiso 1 1 calc R . .
C24 C -0.0471(2) 0.1560(7) 0.0629(4) 0.0397(17) Uani 1 1 d . . .
H24A H -0.0644 0.0747 0.0608 0.060 Uiso 1 1 calc R . .
H24B H -0.0444 0.1767 0.0087 0.060 Uiso 1 1 calc R . .
H24C H -0.0627 0.2279 0.0820 0.060 Uiso 1 1 calc R . .
O1' O 0.36319(14) 0.1116(4) 0.3797(2) 0.0321(11) Uani 1 1 d . . .
O2' O 0.31440(13) -0.0390(4) 0.4050(2) 0.0240(9) Uani 1 1 d . . .
H2' H 0.3348 -0.0488 0.4481 0.036 Uiso 1 1 calc R . .
O3' O 0.44900(13) 0.1832(4) 0.1386(2) 0.0230(9) Uani 1 1 d . . .
O4' O 0.43778(13) 0.3928(4) 0.1013(3) 0.0241(9) Uani 1 1 d . . .
H4' H 0.4165 0.4408 0.0762 0.036 Uiso 1 1 calc R . .
O5' O 0.37253(13) -0.4417(4) 0.0489(2) 0.0207(9) Uani 1 1 d . . .
O6' O 0.40479(14) -0.3049(4) 0.1517(3) 0.0340(11) Uani 1 1 d . . .
N1' N 0.4501(2) 0.9325(6) 0.2122(4) 0.0440(15) Uani 1 1 d . . .
H1'1 H 0.4400 1.0079 0.1837 0.053 Uiso 1 1 calc R . .
H1'2 H 0.4306 0.8660 0.1896 0.053 Uiso 1 1 calc R . .
C1' C 0.32807(18) 0.0484(5) 0.3575(3) 0.0175(12) Uani 1 1 d . . .
C2' C 0.29430(18) 0.0629(6) 0.2733(3) 0.0189(12) Uani 1 1 d . . .
H2'1 H 0.2811 0.1522 0.2684 0.023 Uiso 1 1 calc R . .
H2'2 H 0.2693 -0.0007 0.2686 0.023 Uiso 1 1 calc R . .
C3' C 0.31591(17) 0.0399(5) 0.2018(3) 0.0155(11) Uani 1 1 d . . .
C4' C 0.33513(17) 0.1484(5) 0.1685(3) 0.0143(11) Uani 1 1 d . . .
C5' C 0.33643(19) 0.2875(5) 0.2062(3) 0.0185(12) Uani 1 1 d . . .
H5'1 H 0.3635 0.3346 0.1999 0.022 Uiso 1 1 calc R . .
H5'2 H 0.3395 0.2784 0.2648 0.022 Uiso 1 1 calc R . .
C6' C 0.2934(2) 0.3712(6) 0.1673(4) 0.0302(15) Uani 1 1 d . . .
H6'1 H 0.2912 0.3856 0.1100 0.045 Uiso 1 1 calc R . .
H6'2 H 0.2957 0.4561 0.1950 0.045 Uiso 1 1 calc R . .
H6'3 H 0.2664 0.3246 0.1724 0.045 Uiso 1 1 calc R . .
C7' C 0.35239(17) 0.1260(5) 0.1007(3) 0.0161(11) Uani 1 1 d . . .
C8' C 0.37222(19) 0.2436(5) 0.0642(3) 0.0183(12) Uani 1 1 d . . .
H8'1 H 0.3683 0.2267 0.0060 0.022 Uiso 1 1 calc R . .
H8'2 H 0.3546 0.3234 0.0687 0.022 Uiso 1 1 calc R . .
C9' C 0.42255(17) 0.2704(5) 0.1049(3) 0.0147(11) Uani 1 1 d . . .
C10' C 0.35203(17) -0.0020(5) 0.0667(3) 0.0156(11) Uani 1 1 d . . .
C11' C 0.37287(19) -0.0279(6) -0.0042(3) 0.0197(12) Uani 1 1 d . . .
H11C H 0.3844 -0.1192 -0.0001 0.024 Uiso 1 1 calc R . .
H11D H 0.3991 0.0315 0.0013 0.024 Uiso 1 1 calc R . .
C12' C 0.3394(2) -0.0079(6) -0.0900(3) 0.0258(14) Uani 1 1 d . . .
H12D H 0.3127 -0.0638 -0.0956 0.039 Uiso 1 1 calc R . .
H12E H 0.3545 -0.0317 -0.1315 0.039 Uiso 1 1 calc R . .
H12F H 0.3300 0.0843 -0.0968 0.039 Uiso 1 1 calc R . .
C13' C 0.33314(17) -0.1091(5) 0.1005(3) 0.0138(11) Uani 1 1 d . . .
C14' C 0.33050(18) -0.2453(5) 0.0616(3) 0.0176(12) Uani 1 1 d . . .
H14C H 0.3245 -0.2338 0.0024 0.021 Uiso 1 1 calc R . .
H14D H 0.3043 -0.2924 0.0715 0.021 Uiso 1 1 calc R . .
C15' C 0.37336(18) -0.3341(5) 0.0916(3) 0.0171(12) Uani 1 1 d . . .
C16' C 0.31664(17) -0.0887(5) 0.1704(3) 0.0138(11) Uani 1 1 d . . .
C17' C 0.29992(19) -0.2080(5) 0.2107(3) 0.0202(12) Uani 1 1 d . . .
H17C H 0.3053 -0.1900 0.2692 0.024 Uiso 1 1 calc R . .
H17D H 0.3180 -0.2862 0.2051 0.024 Uiso 1 1 calc R . .
C18' C 0.2486(2) -0.2396(6) 0.1738(4) 0.0319(15) Uani 1 1 d . . .
H18D H 0.2302 -0.1674 0.1856 0.048 Uiso 1 1 calc R . .
H18E H 0.2409 -0.3210 0.1975 0.048 Uiso 1 1 calc R . .
H18F H 0.2424 -0.2501 0.1151 0.048 Uiso 1 1 calc R . .
C19' C 0.4485(2) 0.9517(6) 0.2980(3) 0.0267(14) Uani 1 1 d . . .
H19C H 0.4237 1.0138 0.2979 0.032 Uiso 1 1 calc R . .
H19D H 0.4772 0.9937 0.3283 0.032 Uiso 1 1 calc R . .
C20' C 0.4417(3) 0.8297(9) 0.3434(5) 0.063(2) Uani 1 1 d . . .
H20D H 0.4102 0.7992 0.3203 0.076 Uiso 1 1 calc R . .
H20C H 0.4620 0.7604 0.3326 0.076 Uiso 1 1 calc R . .
C21' C 0.4496(3) 0.8401(11) 0.4314(5) 0.069(3) Uani 1 1 d . . .
H21D H 0.4815 0.8606 0.4564 0.104 Uiso 1 1 calc R . .
H21E H 0.4420 0.7566 0.4527 0.104 Uiso 1 1 calc R . .
H21F H 0.4306 0.9101 0.4437 0.104 Uiso 1 1 calc R . .
C22' C 0.49682(19) 0.8996(6) 0.2031(4) 0.0238(13) Uani 1 1 d . . .
H22C H 0.5171 0.9752 0.2227 0.029 Uiso 1 1 calc R . .
H22D H 0.5089 0.8237 0.2383 0.029 Uiso 1 1 calc R . .
C23' C 0.4984(3) 0.8676(10) 0.1191(5) 0.065(2) Uani 1 1 d . . .
H23C H 0.4835 0.9400 0.0833 0.078 Uiso 1 1 calc R . .
H23D H 0.4801 0.7875 0.1017 0.078 Uiso 1 1 calc R . .
C24' C 0.5441(2) 0.8460(8) 0.1059(5) 0.0464(19) Uani 1 1 d . . .
H24D H 0.5628 0.9243 0.1227 0.070 Uiso 1 1 calc R . .
H24E H 0.5408 0.8291 0.0484 0.070 Uiso 1 1 calc R . .
H24F H 0.5586 0.7703 0.1378 0.070 Uiso 1 1 calc R . .
C23 C 0.0001(3) 0.1383(10) 0.1206(5) 0.063(2) Uani 1 1 d . . .
H23A H 0.0156 0.0668 0.0996 0.075 Uiso 1 1 calc R . .
H23B H 0.0175 0.2199 0.1202 0.075 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.201(6) . ?
O2 C1 1.314(6) . ?
O2 H2 0.8200 . ?
O3 C9 1.214(6) . ?
O4 C9 1.305(6) . ?
O4 H4 0.8200 . ?
O5 C15 1.282(6) . ?
O6 C15 1.226(6) . ?
N1 C19 1.482(8) . ?
N1 C22 1.492(8) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
C1 C2 1.523(7) . ?
C2 C3 1.520(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C16 1.400(7) . ?
C3 C4 1.422(7) . ?
C4 C7 1.394(7) . ?
C4 C5 1.524(7) . ?
C5 C6 1.527(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C10 1.418(7) . ?
C7 C8 1.521(7) . ?
C8 C9 1.511(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 C13 1.390(7) . ?
C10 C11 1.510(7) . ?
C11 C12 1.530(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C16 1.402(7) . ?
C13 C14 1.517(7) . ?
C14 C15 1.527(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 C17 1.519(7) . ?
C17 C18 1.533(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.453(9) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.450(9) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.472(9) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C24 C23 1.496(10) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
O1' C1' 1.199(6) . ?
O2' C1' 1.321(6) . ?
O2' H2' 0.8200 . ?
O3' C9' 1.211(6) . ?
O4' C9' 1.311(6) . ?
O4' H4' 0.8200 . ?
O5' C15' 1.289(6) . ?
O6' C15' 1.218(6) . ?
N1' C19' 1.471(8) . ?
N1' C22' 1.490(8) . ?
N1' H1'1 0.9000 . ?
N1' H1'2 0.9000 . ?
C1' C2' 1.511(7) . ?
C2' C3' 1.532(7) . ?
C2' H2'1 0.9700 . ?
C2' H2'2 0.9700 . ?
C3' C16' 1.391(7) . ?
C3' C4' 1.413(7) . ?
C4' C7' 1.395(7) . ?
C4' C5' 1.522(7) . ?
C5' C6' 1.530(8) . ?
C5' H5'1 0.9700 . ?
C5' H5'2 0.9700 . ?
C6' H6'1 0.9600 . ?
C6' H6'2 0.9600 . ?
C6' H6'3 0.9600 . ?
C7' C10' 1.399(7) . ?
C7' C8' 1.519(7) . ?
C8' C9' 1.507(7) . ?
C8' H8'1 0.9700 . ?
C8' H8'2 0.9700 . ?
C10' C13' 1.401(7) . ?
C10' C11' 1.515(7) . ?
C11' C12' 1.534(8) . ?
C11' H11C 0.9700 . ?
C11' H11D 0.9700 . ?
C12' H12D 0.9600 . ?
C12' H12E 0.9600 . ?
C12' H12F 0.9600 . ?
C13' C16' 1.411(7) . ?
C13' C14' 1.501(7) . ?
C14' C15' 1.532(7) . ?
C14' H14C 0.9700 . ?
C14' H14D 0.9700 . ?
C16' C17' 1.522(7) . ?
C17' C18' 1.533(8) . ?
C17' H17C 0.9700 . ?
C17' H17D 0.9700 . ?
C18' H18D 0.9600 . ?
C18' H18E 0.9600 . ?
C18' H18F 0.9600 . ?
C19' C20' 1.481(10) . ?
C19' H19C 0.9700 . ?
C19' H19D 0.9700 . ?
C20' C21' 1.439(11) . ?
C20' H20D 0.9700 . ?
C20' H20C 0.9700 . ?
C21' H21D 0.9600 . ?
C21' H21E 0.9600 . ?
C21' H21F 0.9600 . ?
C22' C23' 1.462(10) . ?
C22' H22C 0.9700 . ?
C22' H22D 0.9700 . ?
C23' C24' 1.467(10) . ?
C23' H23C 0.9700 . ?
C23' H23D 0.9700 . ?
C24' H24D 0.9600 . ?
C24' H24E 0.9600 . ?
C24' H24F 0.9600 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?

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
C1 O2 H2 109.5 . . ?
C9 O4 H4 109.5 . . ?
C19 N1 C22 113.9(5) . . ?
C19 N1 H1A 108.8 . . ?
C22 N1 H1A 108.8 . . ?
C19 N1 H1B 108.8 . . ?
C22 N1 H1B 108.8 . . ?
H1A N1 H1B 107.7 . . ?
O1 C1 O2 124.2(5) . . ?
O1 C1 C2 123.4(5) . . ?
O2 C1 C2 112.3(5) . . ?
C3 C2 C1 114.0(4) . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C16 C3 C4 120.4(5) . . ?
C16 C3 C2 119.8(5) . . ?
C4 C3 C2 119.9(5) . . ?
C7 C4 C3 119.1(4) . . ?
C7 C4 C5 121.1(4) . . ?
C3 C4 C5 119.8(4) . . ?
C4 C5 C6 113.3(4) . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C6 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 C10 120.6(5) . . ?
C4 C7 C8 118.7(4) . . ?
C10 C7 C8 120.7(5) . . ?
C9 C8 C7 113.2(4) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
O3 C9 O4 119.8(5) . . ?
O3 C9 C8 122.6(5) . . ?
O4 C9 C8 117.6(5) . . ?
C13 C10 C7 119.4(5) . . ?
C13 C10 C11 120.1(5) . . ?
C7 C10 C11 120.4(5) . . ?
C10 C11 C12 115.0(5) . . ?
C10 C11 H11A 108.5 . . ?
C12 C11 H11A 108.5 . . ?
C10 C11 H11B 108.5 . . ?
C12 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
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 . . ?
C10 C13 C16 121.0(5) . . ?
C10 C13 C14 119.5(5) . . ?
C16 C13 C14 119.5(5) . . ?
C13 C14 C15 116.1(4) . . ?
C13 C14 H14A 108.3 . . ?
C15 C14 H14A 108.3 . . ?
C13 C14 H14B 108.3 . . ?
C15 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
O6 C15 O5 123.7(5) . . ?
O6 C15 C14 121.9(5) . . ?
O5 C15 C14 114.4(4) . . ?
C3 C16 C13 119.4(5) . . ?
C3 C16 C17 119.6(5) . . ?
C13 C16 C17 121.0(5) . . ?
C16 C17 C18 114.7(4) . . ?
C16 C17 H17A 108.6 . . ?
C18 C17 H17A 108.6 . . ?
C16 C17 H17B 108.6 . . ?
C18 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 N1 117.1(6) . . ?
C20 C19 H19A 108.0 . . ?
N1 C19 H19A 108.0 . . ?
C20 C19 H19B 108.0 . . ?
N1 C19 H19B 108.0 . . ?
H19A C19 H19B 107.3 . . ?
C21 C20 C19 119.1(7) . . ?
C21 C20 H20A 107.5 . . ?
C19 C20 H20A 107.5 . . ?
C21 C20 H20B 107.5 . . ?
C19 C20 H20B 107.5 . . ?
H20A C20 H20B 107.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 N1 113.4(5) . . ?
C23 C22 H22A 108.9 . . ?
N1 C22 H22A 108.9 . . ?
C23 C22 H22B 108.9 . . ?
N1 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1' O2' H2' 109.5 . . ?
C9' O4' H4' 109.5 . . ?
C19' N1' C22' 114.4(5) . . ?
C19' N1' H1'1 108.7 . . ?
C22' N1' H1'1 108.7 . . ?
C19' N1' H1'2 108.7 . . ?
C22' N1' H1'2 108.7 . . ?
H1'1 N1' H1'2 107.6 . . ?
O1' C1' O2' 123.4(5) . . ?
O1' C1' C2' 123.6(5) . . ?
O2' C1' C2' 113.0(5) . . ?
C1' C2' C3' 113.8(4) . . ?
C1' C2' H2'1 108.8 . . ?
C3' C2' H2'1 108.8 . . ?
C1' C2' H2'2 108.8 . . ?
C3' C2' H2'2 108.8 . . ?
H2'1 C2' H2'2 107.7 . . ?
C16' C3' C4' 120.3(5) . . ?
C16' C3' C2' 119.4(5) . . ?
C4' C3' C2' 120.2(5) . . ?
C7' C4' C3' 119.0(5) . . ?
C7' C4' C5' 121.0(5) . . ?
C3' C4' C5' 120.0(5) . . ?
C4' C5' C6' 113.3(4) . . ?
C4' C5' H5'1 108.9 . . ?
C6' C5' H5'1 108.9 . . ?
C4' C5' H5'2 108.9 . . ?
C6' C5' H5'2 108.9 . . ?
H5'1 C5' H5'2 107.7 . . ?
C5' C6' H6'1 109.5 . . ?
C5' C6' H6'2 109.5 . . ?
H6'1 C6' H6'2 109.5 . . ?
C5' C6' H6'3 109.5 . . ?
H6'1 C6' H6'3 109.5 . . ?
H6'2 C6' H6'3 109.5 . . ?
C4' C7' C10' 121.2(5) . . ?
C4' C7' C8' 118.7(5) . . ?
C10' C7' C8' 120.1(5) . . ?
C9' C8' C7' 114.2(4) . . ?
C9' C8' H8'1 108.7 . . ?
C7' C8' H8'1 108.7 . . ?
C9' C8' H8'2 108.7 . . ?
C7' C8' H8'2 108.7 . . ?
H8'1 C8' H8'2 107.6 . . ?
O3' C9' O4' 119.8(5) . . ?
O3' C9' C8' 122.5(5) . . ?
O4' C9' C8' 117.7(4) . . ?
C7' C10' C13' 119.4(5) . . ?
C7' C10' C11' 121.3(5) . . ?
C13' C10' C11' 119.3(5) . . ?
C10' C11' C12' 114.5(5) . . ?
C10' C11' H11C 108.6 . . ?
C12' C11' H11C 108.6 . . ?
C10' C11' H11D 108.6 . . ?
C12' C11' H11D 108.6 . . ?
H11C C11' H11D 107.6 . . ?
C11' C12' H12D 109.5 . . ?
C11' C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
C11' C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
C10' C13' C16' 120.1(5) . . ?
C10' C13' C14' 119.6(4) . . ?
C16' C13' C14' 120.4(5) . . ?
C13' C14' C15' 116.1(4) . . ?
C13' C14' H14C 108.3 . . ?
C15' C14' H14C 108.3 . . ?
C13' C14' H14D 108.3 . . ?
C15' C14' H14D 108.3 . . ?
H14C C14' H14D 107.4 . . ?
O6' C15' O5' 123.8(5) . . ?
O6' C15' C14' 122.0(5) . . ?
O5' C15' C14' 114.2(5) . . ?
C3' C16' C13' 119.8(5) . . ?
C3' C16' C17' 120.6(5) . . ?
C13' C16' C17' 119.6(5) . . ?
C16' C17' C18' 113.4(5) . . ?
C16' C17' H17C 108.9 . . ?
C18' C17' H17C 108.9 . . ?
C16' C17' H17D 108.9 . . ?
C18' C17' H17D 108.9 . . ?
H17C C17' H17D 107.7 . . ?
C17' C18' H18D 109.5 . . ?
C17' C18' H18E 109.5 . . ?
H18D C18' H18E 109.5 . . ?
C17' C18' H18F 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 109.5 . . ?
N1' C19' C20' 116.5(6) . . ?
N1' C19' H19C 108.2 . . ?
C20' C19' H19C 108.2 . . ?
N1' C19' H19D 108.2 . . ?
C20' C19' H19D 108.2 . . ?
H19C C19' H19D 107.3 . . ?
C21' C20' C19' 117.7(8) . . ?
C21' C20' H20D 107.9 . . ?
C19' C20' H20D 107.9 . . ?
C21' C20' H20C 107.9 . . ?
C19' C20' H20C 107.9 . . ?
H20D C20' H20C 107.2 . . ?
C20' C21' H21D 109.5 . . ?
C20' C21' H21E 109.5 . . ?
H21D C21' H21E 109.5 . . ?
C20' C21' H21F 109.5 . . ?
H21D C21' H21F 109.5 . . ?
H21E C21' H21F 109.5 . . ?
C23' C22' N1' 115.2(6) . . ?
C23' C22' H22C 108.5 . . ?
N1' C22' H22C 108.5 . . ?
C23' C22' H22D 108.5 . . ?
N1' C22' H22D 108.5 . . ?
H22C C22' H22D 107.5 . . ?
C22' C23' C24' 117.2(7) . . ?
C22' C23' H23C 108.0 . . ?
C24' C23' H23C 108.0 . . ?
C22' C23' H23D 108.0 . . ?
C24' C23' H23D 108.0 . . ?
H23C C23' H23D 107.2 . . ?
C23' C24' H24D 109.5 . . ?
C23' C24' H24E 109.5 . . ?
H24D C24' H24E 109.5 . . ?
C23' C24' H24F 109.5 . . ?
H24D C24' H24F 109.5 . . ?
H24E C24' H24F 109.5 . . ?
C22 C23 C24 115.5(7) . . ?
C22 C23 H23A 108.4 . . ?
C24 C23 H23A 108.4 . . ?
C22 C23 H23B 108.4 . . ?
C24 C23 H23B 108.4 . . ?
H23A C23 H23B 107.5 . . ?

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
O4 H4 O5 0.82 1.70 2.520(5) 172.3 1_545
O2' H2' O5' 0.82 1.77 2.583(5) 170.8 4_556
O4' H4' O5' 0.82 1.73 2.533(5) 165.0 1_565
N1' H1'1 O3' 0.90 1.95 2.788(7) 153.3 1_565
N1' H1'2 O6' 0.90 1.91 2.785(7) 163.5 1_565

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        24.96
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.959
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.096
# start Validation Reply Form
_vrf_DIFMX01_ta1175_2            
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*2.00
RESPONSE: We were unable to find out suitable model for the 
smeared electron densities (1.96 e/angstrom cube 1.23 angstrom 
away from H22D) present in the e-map.
;
_vrf_PLAT097_ta1175_2            
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.96 eA-3  
RESPONSE: Large Reported Max.  (Positive) Residual Density       1.96 eA-3  
RESPONSE: We were unable to find out suitable model for the 
smeared electron densities (1.96 e/angstrom cube1.23 angstrom 
away from H22D) present in the e-map.
;
# end Validation Reply Form
_database_code_depnum_ccdc_archive 'CCDC 929279'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ta1185b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         2(C18H23O6),2(C8H20N),2(H2O)
_chemical_formula_sum            'C52 H68 N2 O14'
_chemical_formula_weight         967.28

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

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   P21/C
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   33.1689(10)
_cell_length_b                   10.1077(3)
_cell_length_c                   16.6962(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.568(2)
_cell_angle_gamma                90.00
_cell_volume                     5441.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2024
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9714
_exptl_absorpt_correction_T_max  0.9770
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 CCD AREA DETECTOR'
_diffrn_measurement_method       'PHI-OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            62465
_diffrn_reflns_av_R_equivalents  0.0739
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         0.63
_diffrn_reflns_theta_max         21.29
_reflns_number_total             6060
_reflns_number_gt                5007
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER APEX II'
_computing_cell_refinement       'BRUKER APEX II'
_computing_data_reduction        'BRUKER APEX II'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'MERCURY 2.3, PLATON'
_computing_publication_material  'MERCURY 2.3, PLATON'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1385P)²+10.1369P] where P=(Fo²+2Fc²)/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         6060
_refine_ls_number_parameters     607
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0767
_refine_ls_wR_factor_ref         0.2351
_refine_ls_wR_factor_gt          0.2162
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.06986(9) 0.1879(3) 0.9269(2) 0.0567(9) Uani 1 1 d . . .
O2 O 0.08031(9) 0.3936(3) 0.9661(2) 0.0589(10) Uani 1 1 d . . .
H2 H 0.0999 0.4448 0.9793 0.088 Uiso 1 1 calc R . .
O3 O 0.13965(9) -0.4380(3) 1.00741(19) 0.0490(9) Uani 1 1 d . . .
O4 O 0.10668(10) -0.2880(3) 0.9198(2) 0.0510(9) Uani 1 1 d . . .
O5A O 0.1403(4) -0.0102(14) 0.6872(7) 0.054(3) Uiso 0.29 1 d P A 1
C21A C 0.0333(4) 1.2100(10) 0.6983(6) 0.067(3) Uiso 0.56 1 d PD B 1
C22A C 0.0661(5) 1.2746(17) 0.6597(10) 0.103(4) Uiso 0.57 1 d P B 1
C24A C 0.0771(6) 0.7231(18) 0.6995(11) 0.080(5) Uiso 0.41 1 d P B 1
O5B O 0.14152(15) 0.0593(6) 0.6839(3) 0.0480(13) Uiso 0.71 1 d P A 2
C21B C 0.0605(6) 1.2084(17) 0.7080(11) 0.089(5) Uiso 0.44 1 d P B 2
C22B C 0.0513(8) 1.340(3) 0.6671(15) 0.133(8) Uiso 0.43 1 d P B 2
C24B C 0.0932(3) 0.7610(10) 0.6993(6) 0.058(3) Uiso 0.59 1 d P B 2
O6 O 0.19404(9) -0.0226(3) 0.6388(2) 0.0515(9) Uani 1 1 d . A .
O7 O 0.06440(11) 0.9378(4) 0.8549(2) 0.0515(9) Uani 1 1 d . . .
N1 N 0.05807(12) 0.9711(4) 0.6898(2) 0.0510(11) Uani 1 1 d . B .
H1A H 0.0819 0.9950 0.6768 0.061 Uiso 1 1 calc R . .
H1B H 0.0631 0.9687 0.7452 0.061 Uiso 1 1 calc R . .
C1 C 0.09424(13) 0.2737(5) 0.9575(3) 0.0414(11) Uani 1 1 d . . .
C2 C 0.13995(12) 0.2484(4) 0.9910(3) 0.0381(11) Uani 1 1 d . . .
H2A H 0.1450 0.2368 1.0502 0.046 Uiso 1 1 calc R . .
H2B H 0.1552 0.3262 0.9810 0.046 Uiso 1 1 calc R . .
C3 C 0.15700(11) 0.1295(4) 0.9549(3) 0.0315(10) Uani 1 1 d . . .
C4 C 0.15728(12) 0.0045(4) 0.9918(2) 0.0305(10) Uani 1 1 d . . .
C5 C 0.13830(13) -0.0129(4) 1.0655(3) 0.0403(11) Uani 1 1 d . . .
H5A H 0.1265 -0.1009 1.0635 0.048 Uiso 1 1 calc R . .
H5B H 0.1158 0.0502 1.0612 0.048 Uiso 1 1 calc R . .
C6 C 0.16873(16) 0.0056(5) 1.1485(3) 0.0539(13) Uani 1 1 d . . .
H6A H 0.1915 -0.0548 1.1530 0.081 Uiso 1 1 calc R . .
H6B H 0.1549 -0.0114 1.1920 0.081 Uiso 1 1 calc R . .
H6C H 0.1790 0.0948 1.1530 0.081 Uiso 1 1 calc R . .
C7 C 0.17341(12) -0.1042(4) 0.9589(2) 0.0315(10) Uani 1 1 d . . .
C8 C 0.17488(13) -0.2372(4) 1.0002(3) 0.0372(11) Uani 1 1 d . . .
H8A H 0.1790 -0.2231 1.0590 0.045 Uiso 1 1 calc R . .
H8B H 0.1989 -0.2848 0.9915 0.045 Uiso 1 1 calc R . .
C9 C 0.13701(13) -0.3243(4) 0.9715(3) 0.0338(10) Uani 1 1 d . . .
C10 C 0.18827(13) -0.0911(4) 0.8872(3) 0.0365(11) Uani 1 1 d . . .
C11 C 0.20159(15) -0.2114(5) 0.8462(3) 0.0526(13) Uani 1 1 d . . .
H11A H 0.1852 -0.2868 0.8556 0.063 Uiso 1 1 calc R . .
H11B H 0.1959 -0.1963 0.7873 0.063 Uiso 1 1 calc R . .
C12 C 0.24641(16) -0.2432(6) 0.8771(4) 0.0689(16) Uani 1 1 d . . .
H12A H 0.2629 -0.1740 0.8616 0.103 Uiso 1 1 calc R . .
H12B H 0.2525 -0.3254 0.8537 0.103 Uiso 1 1 calc R . .
H12C H 0.2528 -0.2507 0.9361 0.103 Uiso 1 1 calc R . .
C13 C 0.18922(12) 0.0345(4) 0.8512(2) 0.0330(10) Uani 1 1 d . . .
C14 C 0.20731(13) 0.0483(4) 0.7771(3) 0.0391(11) Uani 1 1 d . A .
H14A H 0.2177 0.1377 0.7758 0.047 Uiso 1 1 calc R . .
H14B H 0.2307 -0.0114 0.7833 0.047 Uiso 1 1 calc R . .
C15 C 0.17764(13) 0.0202(4) 0.6963(3) 0.0402(11) Uani 1 1 d . . .
C16 C 0.17268(12) 0.1448(4) 0.8848(2) 0.0314(10) Uani 1 1 d . . .
C17 C 0.17202(13) 0.2798(4) 0.8444(3) 0.0401(11) Uani 1 1 d . . .
H17A H 0.1690 0.2679 0.7857 0.048 Uiso 1 1 calc R . .
H17B H 0.1481 0.3287 0.8523 0.048 Uiso 1 1 calc R . .
C18 C 0.21077(16) 0.3606(5) 0.8785(3) 0.0576(14) Uani 1 1 d . . .
H18A H 0.2127 0.3798 0.9355 0.086 Uiso 1 1 calc R . .
H18B H 0.2094 0.4418 0.8482 0.086 Uiso 1 1 calc R . .
H18C H 0.2347 0.3112 0.8732 0.086 Uiso 1 1 calc R . .
C19 C 0.0266(3) 1.0792(6) 0.6602(4) 0.091(2) Uani 1 1 d D . .
C20 C -0.0127(2) 1.0470(10) 0.6861(6) 0.142(4) Uani 1 1 d . B .
H20A H -0.0068 1.0369 0.7449 0.213 Uiso 1 1 calc R . .
H20B H -0.0241 0.9660 0.6603 0.213 Uiso 1 1 calc R . .
H20C H -0.0323 1.1174 0.6697 0.213 Uiso 1 1 calc R . .
C23 C 0.04794(17) 0.8325(5) 0.6586(3) 0.0622(15) Uani 1 1 d . . .
C25 C 0.0384(2) 0.8270(6) 0.5660(4) 0.0787(18) Uani 1 1 d . B .
H25A H 0.0621 0.8577 0.5465 0.094 Uiso 1 1 calc R . .
H25B H 0.0150 0.8837 0.5429 0.094 Uiso 1 1 calc R . .
C26 C 0.0282(2) 0.6811(8) 0.5385(5) 0.104(2) Uani 1 1 d . . .
H26A H 0.0476 0.6229 0.5732 0.156 Uiso 1 1 calc R B .
H26B H 0.0300 0.6705 0.4824 0.156 Uiso 1 1 calc R . .
H26C H 0.0006 0.6600 0.5431 0.156 Uiso 1 1 calc R . .
O1' O 0.36033(9) 1.4568(3) 0.8684(2) 0.0499(9) Uani 1 1 d . . .
O2' O 0.39366(10) 1.3043(3) 0.8145(2) 0.0522(9) Uani 1 1 d . . .
O3' O 0.42904(10) 0.8352(4) 0.8662(2) 0.0653(11) Uani 1 1 d . . .
O4' O 0.41892(9) 0.6264(2) 0.88741(10) 0.0655(11) Uani 1 1 d . . .
H4' H 0.3994 0.5750 0.8834 0.098 Uiso 1 1 calc R . .
O5'A O 0.35962(6) 0.94070(18) 0.55042(11) 0.0330(14) Uiso 0.48 1 d PR C 1
C21' C 0.46368(6) 0.70715(18) 0.16935(13) 0.084(4) Uiso 0.51 1 d PR D 1
C24' C 0.42954(6) 0.20510(18) 0.12435(11) 0.080(4) Uiso 0.44 1 d PR D 1
O5'B O 0.35937(6) 1.02782(18) 0.55024(11) 0.089(2) Uiso 0.52 1 d PR C 2
C21" C 0.43831(6) 0.68979(18) 0.15108(12) 0.101(5) Uiso 0.49 1 d PR D 2
C24" C 0.40907(6) 0.25242(18) 0.11337(11) 0.069(3) Uiso 0.56 1 d PR D 2
O6' O 0.30714(5) 1.00574(18) 0.45127(10) 0.0596(10) Uani 1 1 d R C .
O7' O 0.43637(5) 0.07739(18) 0.79381(12) 0.0561(10) Uani 1 1 d R . .
N1' N 0.44201(6) 0.46235(18) 0.13458(12) 0.0575(12) Uani 1 1 d R D .
H1'1 H 0.4174 0.4833 0.1010 0.069 Uiso 1 1 calc R . .
H1'2 H 0.4379 0.4569 0.1859 0.069 Uiso 1 1 calc R . .
C1' C 0.36308(13) 1.3419(4) 0.8364(3) 0.0348(10) Uani 1 1 d . . .
C2' C 0.32465(13) 1.2571(4) 0.8282(3) 0.0383(11) Uani 1 1 d . . .
H2'1 H 0.3193 1.2461 0.8825 0.046 Uiso 1 1 calc R . .
H2'2 H 0.3013 1.3047 0.7947 0.046 Uiso 1 1 calc R . .
C3' C 0.32625(12) 1.1215(4) 0.7908(3) 0.0335(10) Uani 1 1 d . . .
C4' C 0.34130(12) 1.0132(4) 0.8412(3) 0.0324(10) Uani 1 1 d . . .
C5' C 0.35827(15) 1.0334(5) 0.9333(3) 0.0464(12) Uani 1 1 d . . .
H5'1 H 0.3699 1.1216 0.9425 0.056 Uiso 1 1 calc R . .
H5'2 H 0.3805 0.9706 0.9528 0.056 Uiso 1 1 calc R . .
C6' C 0.32549(18) 1.0164(6) 0.9837(3) 0.0653(15) Uani 1 1 d . . .
H6'1 H 0.3021 1.0721 0.9613 0.098 Uiso 1 1 calc R . .
H6'2 H 0.3372 1.0407 1.0399 0.098 Uiso 1 1 calc R . .
H6'3 H 0.3167 0.9257 0.9813 0.098 Uiso 1 1 calc R . .
C7' C 0.34193(12) 0.8874(4) 0.8065(3) 0.0331(10) Uani 1 1 d . . .
C8' C 0.35900(13) 0.7701(4) 0.8595(3) 0.0392(11) Uani 1 1 d . . .
H8'1 H 0.3534 0.7825 0.9135 0.047 Uiso 1 1 calc R . .
H8'2 H 0.3442 0.6916 0.8355 0.047 Uiso 1 1 calc R . .
C9' C 0.40473(14) 0.7464(5) 0.8702(3) 0.0459(12) Uani 1 1 d . . .
C10' C 0.32704(12) 0.8695(4) 0.7210(3) 0.0352(11) Uani 1 1 d . . .
C11' C 0.32734(14) 0.7328(4) 0.6833(3) 0.0473(12) Uani 1 1 d . . .
H11C H 0.3506 0.6832 0.7154 0.057 Uiso 1 1 calc R . .
H11D H 0.3315 0.7421 0.6280 0.057 Uiso 1 1 calc R . .
C12' C 0.28763(17) 0.6540(5) 0.6791(4) 0.0672(16) Uani 1 1 d . . .
H12D H 0.2851 0.6339 0.7340 0.101 Uiso 1 1 calc R . .
H12E H 0.2886 0.5732 0.6494 0.101 Uiso 1 1 calc R . .
H12F H 0.2642 0.7055 0.6514 0.101 Uiso 1 1 calc R . .
C13' C 0.31162(12) 0.9783(4) 0.6716(3) 0.0352(11) Uani 1 1 d . . .
C14' C 0.29348(13) 0.9611(5) 0.5799(3) 0.0449(12) Uani 1 1 d . C .
H14C H 0.2825 0.8720 0.5704 0.054 Uiso 1 1 calc R . .
H14D H 0.2704 1.0219 0.5632 0.054 Uiso 1 1 calc R . .
C15' C 0.32299(13) 0.9834(5) 0.5265(3) 0.0464(12) Uani 1 1 d . . .
C16' C 0.31268(12) 1.1052(4) 0.7055(3) 0.0341(10) Uani 1 1 d . . .
C17' C 0.30102(13) 1.2245(5) 0.6499(3) 0.0466(12) Uani 1 1 d . . .
H17C H 0.3075 1.2056 0.5973 0.056 Uiso 1 1 calc R . .
H17D H 0.3181 1.2988 0.6743 0.056 Uiso 1 1 calc R . .
C18' C 0.25522(14) 1.2655(5) 0.6341(3) 0.0559(14) Uani 1 1 d . . .
H18D H 0.2380 1.1919 0.6117 0.084 Uiso 1 1 calc R . .
H18E H 0.2501 1.3377 0.5957 0.084 Uiso 1 1 calc R . .
H18F H 0.2490 1.2926 0.6850 0.084 Uiso 1 1 calc R . .
C19' C 0.4707(3) 0.5755(6) 0.1334(5) 0.088(2) Uani 1 1 d . . .
C20' C 0.5111(2) 0.5470(9) 0.1936(6) 0.136(4) Uani 1 1 d . D .
H20D H 0.5295 0.6206 0.1952 0.204 Uiso 1 1 calc R . .
H20E H 0.5233 0.4690 0.1767 0.204 Uiso 1 1 calc R . .
H20F H 0.5062 0.5334 0.2474 0.204 Uiso 1 1 calc R . .
C22' C 0.4372(4) 0.8010(13) 0.1106(8) 0.188(5) Uani 1 1 d . . .
C23' C 0.45334(19) 0.3274(6) 0.1111(3) 0.0728(17) Uani 1 1 d . . .
C25' C 0.4607(2) 0.3286(7) 0.0255(4) 0.087(2) Uani 1 1 d D D .
H25C H 0.4833 0.3881 0.0228 0.104 Uiso 1 1 calc R . .
H25D H 0.4360 0.3578 -0.0140 0.104 Uiso 1 1 calc R . .
C26' C 0.4719(2) 0.1838(8) 0.0061(5) 0.117(3) Uani 1 1 d D . .
H26D H 0.5002 0.1658 0.0332 0.176 Uiso 1 1 calc R D .
H26E H 0.4682 0.1734 -0.0523 0.176 Uiso 1 1 calc R . .
H26F H 0.4540 0.1231 0.0256 0.176 Uiso 1 1 calc R . .
H7' H 0.4208(14) 0.132(5) 0.799(3) 0.044(14) Uiso 1 1 d . . .
H7" H 0.429(2) -0.002(7) 0.815(4) 0.11(2) Uiso 1 1 d . . .
H7A H 0.068(2) 1.009(7) 0.879(4) 0.09(2) Uiso 1 1 d . . .
H7B H 0.0819(18) 0.874(6) 0.878(3) 0.074(19) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.214(5) . ?
O2 C1 1.316(5) . ?
O3 C9 1.290(5) . ?
O4 C9 1.218(5) . ?
O5A C15 1.250(13) . ?
C21A C19 1.462(10) . ?
C21A C22A 1.53(2) . ?
C24A C23 1.520(18) . ?
O5B C15 1.232(6) . ?
C21B C22B 1.49(3) . ?
C21B C19 1.785(19) . ?
C24B C23 1.660(11) . ?
O6 C15 1.284(5) . ?
N1 C23 1.505(7) . ?
N1 C19 1.511(7) . ?
C1 C2 1.509(6) . ?
C2 C3 1.512(6) . ?
C3 C16 1.396(6) . ?
C3 C4 1.405(6) . ?
C4 C7 1.391(6) . ?
C4 C5 1.518(6) . ?
C5 C6 1.523(6) . ?
C7 C10 1.403(6) . ?
C7 C8 1.507(6) . ?
C8 C9 1.516(6) . ?
C10 C13 1.408(6) . ?
C10 C11 1.511(6) . ?
C11 C12 1.490(7) . ?
C13 C16 1.416(6) . ?
C13 C14 1.503(6) . ?
C14 C15 1.499(6) . ?
C16 C17 1.520(6) . ?
C17 C18 1.516(6) . ?
C19 C20 1.505(12) . ?
C23 C25 1.505(8) . ?
C25 C26 1.558(9) . ?
O1' C1' 1.291(5) . ?
O2' C1' 1.217(5) . ?
O3' C9' 1.219(5) . ?
O4' C9' 1.308(5) . ?
O5'A C15' 1.263(5) . ?
C21' C22' 1.493(10) . ?
C21' C19' 1.500(6) . ?
C24' C23' 1.511(7) . ?
O5'B C15' 1.261(5) . ?
C21" C22' 1.308(11) . ?
C21" C19' 1.650(7) . ?
C24" C23' 1.661(7) . ?
O6' C15' 1.263(5) . ?
N1' C19' 1.490(6) . ?
N1' C23' 1.492(6) . ?
C1' C2' 1.516(6) . ?
C2' C3' 1.511(6) . ?
C3' C4' 1.399(6) . ?
C3' C16' 1.400(6) . ?
C4' C7' 1.400(6) . ?
C4' C5' 1.521(6) . ?
C5' C6' 1.533(7) . ?
C7' C10' 1.409(6) . ?
C7' C8' 1.507(6) . ?
C8' C9' 1.505(6) . ?
C10' C13' 1.398(6) . ?
C10' C11' 1.520(6) . ?
C11' C12' 1.526(7) . ?
C13' C16' 1.400(6) . ?
C13' C14' 1.517(6) . ?
C14' C15' 1.488(6) . ?
C16' C17' 1.516(6) . ?
C17' C18' 1.537(6) . ?
C19' C20' 1.503(12) . ?
C23' C25' 1.505(8) . ?
C25' C26' 1.562(9) . ?

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
C19 C21A C22A 104.6(10) . . ?
C22B C21B C19 114.0(14) . . ?
C23 N1 C19 118.6(4) . . ?
O1 C1 O2 119.2(4) . . ?
O1 C1 C2 123.1(4) . . ?
O2 C1 C2 117.6(4) . . ?
C1 C2 C3 115.1(4) . . ?
C16 C3 C4 120.1(4) . . ?
C16 C3 C2 119.6(4) . . ?
C4 C3 C2 120.3(4) . . ?
C7 C4 C3 120.1(4) . . ?
C7 C4 C5 120.0(4) . . ?
C3 C4 C5 119.9(4) . . ?
C4 C5 C6 114.3(4) . . ?
C4 C7 C10 120.5(4) . . ?
C4 C7 C8 119.9(4) . . ?
C10 C7 C8 119.6(4) . . ?
C7 C8 C9 116.0(3) . . ?
O4 C9 O3 123.5(4) . . ?
O4 C9 C8 122.3(4) . . ?
O3 C9 C8 114.2(4) . . ?
C7 C10 C13 119.8(4) . . ?
C7 C10 C11 120.6(4) . . ?
C13 C10 C11 119.6(4) . . ?
C12 C11 C10 113.0(4) . . ?
C10 C13 C16 119.4(4) . . ?
C10 C13 C14 119.2(4) . . ?
C16 C13 C14 121.3(4) . . ?
C15 C14 C13 114.8(4) . . ?
O5B C15 O6 123.2(4) . . ?
O5A C15 O6 114.1(7) . . ?
O5B C15 C14 119.8(4) . . ?
O5A C15 C14 125.3(7) . . ?
O6 C15 C14 115.6(4) . . ?
C3 C16 C13 120.0(4) . . ?
C3 C16 C17 120.1(4) . . ?
C13 C16 C17 119.8(4) . . ?
C18 C17 C16 113.2(4) . . ?
C21A C19 C20 97.0(7) . . ?
C21A C19 N1 119.3(7) . . ?
C20 C19 N1 109.1(6) . . ?
C20 C19 C21B 121.8(8) . . ?
N1 C19 C21B 94.0(7) . . ?
N1 C23 C25 111.5(5) . . ?
N1 C23 C24A 117.0(8) . . ?
C25 C23 C24A 113.1(8) . . ?
N1 C23 C24B 99.0(5) . . ?
C25 C23 C24B 110.9(5) . . ?
C23 C25 C26 108.4(6) . . ?
C22' C21' C19' 115.0(7) . . ?
C22' C21" C19' 116.7(6) . . ?
C19' N1' C23' 119.8(4) . . ?
O2' C1' O1' 123.4(4) . . ?
O2' C1' C2' 122.6(4) . . ?
O1' C1' C2' 114.0(4) . . ?
C3' C2' C1' 116.1(3) . . ?
C4' C3' C16' 120.3(4) . . ?
C4' C3' C2' 120.2(4) . . ?
C16' C3' C2' 119.5(4) . . ?
C3' C4' C7' 120.0(4) . . ?
C3' C4' C5' 119.9(4) . . ?
C7' C4' C5' 120.1(4) . . ?
C4' C5' C6' 113.4(4) . . ?
C4' C7' C10' 120.0(4) . . ?
C4' C7' C8' 120.7(4) . . ?
C10' C7' C8' 119.2(4) . . ?
C9' C8' C7' 115.1(4) . . ?
O3' C9' O4' 119.1(4) . . ?
O3' C9' C8' 122.5(4) . . ?
O4' C9' C8' 118.4(4) . . ?
C13' C10' C7' 119.3(4) . . ?
C13' C10' C11' 120.5(4) . . ?
C7' C10' C11' 120.1(4) . . ?
C10' C11' C12' 113.8(4) . . ?
C10' C13' C16' 120.7(4) . . ?
C10' C13' C14' 120.6(4) . . ?
C16' C13' C14' 118.7(4) . . ?
C15' C14' C13' 115.2(4) . . ?
O5'B C15' O6' 113.2(4) . . ?
O5'A C15' O6' 121.4(4) . . ?
O5'B C15' C14' 125.5(4) . . ?
O5'A C15' C14' 118.6(4) . . ?
O6' C15' C14' 116.4(3) . . ?
C3' C16' C13' 119.4(4) . . ?
C3' C16' C17' 120.3(4) . . ?
C13' C16' C17' 120.2(4) . . ?
C16' C17' C18' 114.8(4) . . ?
N1' C19' C21' 121.1(4) . . ?
N1' C19' C20' 108.4(5) . . ?
C21' C19' C20' 95.7(6) . . ?
N1' C19' C21" 95.3(4) . . ?
C20' C19' C21" 122.0(6) . . ?
N1' C23' C25' 110.5(5) . . ?
N1' C23' C24' 122.5(4) . . ?
C25' C23' C24' 110.7(4) . . ?
N1' C23' C24" 97.6(4) . . ?
C25' C23' C24" 111.5(4) . . ?
C23' C25' C26' 106.8(6) . . ?

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
O2 H2 O3 0.82 1.75 2.571(4) 176.5 1_565
N1 H1A O5A 0.90 1.91 2.745(13) 154.4 1_565
N1 H1B O7 0.90 1.85 2.736(5) 167.8 1
O4' H4' O1' 0.82 1.74 2.555(4) 174.4 1_545
N1' H1'2 O7' 0.90 1.85 2.738 170.0 4_565

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        21.29
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.853
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.070
# start Validation Reply Form
_vrf_THETM01_ta1185b             
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The crystal was poorly diffracting at higher Bragg angles and 
the problem could not be resolved even after collecting fresh data set on 
various crystals.
;
_vrf_DIFMX01_ta1185b             
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00
RESPONSE: We were unable to find out suitable model for the smeared electron 
densities (0.85 e/angstrom cube 1.12 angstrom away from H26F) present in the 
e-map.
;
_vrf_PLAT043_ta1185b             
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..      22.20 Check 
RESPONSE: It was not possible to locate eight hydrogen atoms of the disordered 
cationic moity and as a result the calculated and reported molecular weight
differ by 22.20.
;
_vrf_PLAT097_ta1185b             
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.85 eA-3  
RESPONSE: We were unable to find out suitable model for the smeared electron 
densities (0.85 e/angstrom cube 1.12 angstrom away from H26F) present in the 
e-map.
;
_vrf_PLAT201_ta1185b             
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          2 Why ? 
RESPONSE: This was due to the presence of disordered atoms which 
were not treated anisotropically.
;
_vrf_PLAT327_ta1185b             
;
PROBLEM: Check for Possibly Missing H on sp3? Carbon ....       C19'       
RESPONSE: The H-atoms associated with C-atoms adjacent to disordered atoms 
were not located in the e-map.
;
# end Validation Reply Form 


_database_code_depnum_ccdc_archive 'CCDC 929280'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_tapas2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 O6, C6 H12 N'
_chemical_formula_sum            'C21 H29 N O6'
_chemical_formula_weight         391.46

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

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   13.957(4)
_cell_length_b                   10.086(3)
_cell_length_c                   17.006(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.026(5)
_cell_angle_gamma                90.00
_cell_volume                     2203.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9708
_exptl_absorpt_correction_T_max  0.9815
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 CCD AREA DETECTOR'
_diffrn_measurement_method       'PHI-OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11542
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2642
_reflns_number_gt                2186
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER APEX II'
_computing_cell_refinement       'BRUKER APEX II'
_computing_data_reduction        'BRUKER APEX II'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'MERCURY 2.3, PLATON'
_computing_publication_material  'MERCURY 2.3, PLATON'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1445P)²+0.3674P] where P=(Fo²+2Fc²)/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         2642
_refine_ls_number_parameters     255
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.2040
_refine_ls_wR_factor_gt          0.1932
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.098
_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
C18A C 0.3282(6) 0.7661(7) 0.3411(5) 0.0788(17) Uiso 0.68 1 d PD A 1
C20A C 0.4976(8) 0.8163(8) 0.1233(6) 0.0705(19) Uiso 0.55 1 d P B 1
C21A C 0.5902(13) 0.8028(13) 0.1213(10) 0.091(3) Uiso 0.45 1 d P B 1
C18B C 0.375(2) 0.859(2) 0.4044(16) 0.109(6) Uiso 0.32 1 d P A 2
C20B C 0.5564(7) 0.8341(7) 0.1575(5) 0.0456(15) Uiso 0.45 1 d P B 2
C21B C 0.5394(9) 0.8091(10) 0.0740(8) 0.089(3) Uiso 0.55 1 d P B 2
O1 O 0.19253(19) 0.1278(2) 0.34807(14) 0.0496(6) Uani 1 1 d . . .
O2 O 0.09383(18) -0.0447(3) 0.35098(14) 0.0520(6) Uani 1 1 d . . .
H2 H 0.1385 -0.0534 0.3994 0.078 Uiso 1 1 calc R . .
O3 O 0.2824(2) -0.2997(2) 0.12847(17) 0.0631(8) Uani 1 1 d . . .
O4 O 0.22421(17) -0.41462(18) 0.00900(14) 0.0414(5) Uani 1 1 d . . .
O5 O 0.36864(16) 0.42420(17) 0.09106(16) 0.0440(6) Uani 1 1 d . . .
H5 H 0.3189 0.4719 0.0645 0.066 Uiso 1 1 calc R . .
O6 O 0.39581(16) 0.22024(18) 0.14280(14) 0.0397(5) Uani 1 1 d . . .
N1 N 0.4362(2) 0.8598(2) 0.23642(18) 0.0438(6) Uani 1 1 d . A .
H1A H 0.3853 0.8075 0.2011 0.053 Uiso 1 1 calc R . .
H1B H 0.4822 0.8077 0.2765 0.053 Uiso 1 1 calc R . .
C1 C 0.1180(2) 0.0572(3) 0.31305(18) 0.0353(6) Uani 1 1 d . . .
C2 C 0.0420(2) 0.0749(3) 0.22037(18) 0.0372(7) Uani 1 1 d . . .
H2A H 0.0122 0.1632 0.2133 0.045 Uiso 1 1 calc R . .
H2B H -0.0144 0.0116 0.2078 0.045 Uiso 1 1 calc R . .
C3 C 0.09418(19) 0.0554(2) 0.15621(16) 0.0280(6) Uani 1 1 d . . .
C4 C 0.13874(18) 0.1665(2) 0.13196(16) 0.0273(5) Uani 1 1 d . . .
C5 C 0.1422(2) 0.3034(3) 0.17160(19) 0.0375(6) Uani 1 1 d . . .
H5A H 0.2011 0.3518 0.1709 0.056 Uiso 1 1 calc R . .
H5B H 0.1483 0.2935 0.2295 0.056 Uiso 1 1 calc R . .
H5C H 0.0795 0.3508 0.1393 0.056 Uiso 1 1 calc R . .
C6 C 0.18049(18) 0.1490(2) 0.06907(16) 0.0264(6) Uani 1 1 d . . .
C7 C 0.2235(2) 0.2703(3) 0.03960(18) 0.0328(6) Uani 1 1 d . . .
H7A H 0.2185 0.2548 -0.0182 0.039 Uiso 1 1 calc R . .
H7B H 0.1802 0.3463 0.0381 0.039 Uiso 1 1 calc R . .
C8 C 0.3354(2) 0.3035(2) 0.09569(17) 0.0294(6) Uani 1 1 d . . .
C9 C 0.18130(19) 0.0225(2) 0.03341(16) 0.0280(6) Uani 1 1 d . . .
C10 C 0.2330(2) 0.0047(3) -0.03034(19) 0.0422(7) Uani 1 1 d . . .
H10A H 0.1848 0.0292 -0.0864 0.063 Uiso 1 1 calc R . .
H10B H 0.2530 -0.0863 -0.0306 0.063 Uiso 1 1 calc R . .
H10C H 0.2936 0.0601 -0.0140 0.063 Uiso 1 1 calc R . .
C11 C 0.13543(19) -0.0866(2) 0.05733(17) 0.0285(6) Uani 1 1 d . . .
C12 C 0.1273(2) -0.2201(3) 0.01280(18) 0.0363(6) Uani 1 1 d . . .
H12A H 0.1198 -0.2037 -0.0455 0.044 Uiso 1 1 calc R . .
H12B H 0.0645 -0.2641 0.0104 0.044 Uiso 1 1 calc R . .
C13 C 0.2200(2) -0.3151(2) 0.05486(17) 0.0315(6) Uani 1 1 d . . .
C14 C 0.0940(2) -0.0712(2) 0.12087(17) 0.0301(6) Uani 1 1 d . . .
C15 C 0.0510(2) -0.1916(3) 0.1502(2) 0.0416(7) Uani 1 1 d . . .
H15A H -0.0221 -0.1999 0.1162 0.062 Uiso 1 1 calc R . .
H15B H 0.0616 -0.1809 0.2092 0.062 Uiso 1 1 calc R . .
H15C H 0.0864 -0.2700 0.1439 0.062 Uiso 1 1 calc R . .
C16 C 0.3903(3) 0.9560(3) 0.2789(2) 0.0537(9) Uani 1 1 d . A .
H16A H 0.4433 1.0192 0.3115 0.064 Uiso 1 1 calc R . .
H16B H 0.3346 1.0046 0.2355 0.064 Uiso 1 1 calc R . .
C17 C 0.3493(3) 0.8894(6) 0.3358(4) 0.0820(14) Uani 1 1 d D . .
C19 C 0.4911(4) 0.9288(4) 0.1853(3) 0.0693(12) Uani 1 1 d . . .


_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
C18A C17 1.289(8) . ?
C20A C21A 1.313(17) . ?
C20A C19 1.576(9) . ?
C18B C17 1.12(2) . ?
C20B C21B 1.370(13) . ?
C20B C19 1.518(8) . ?
O1 C1 1.208(4) . ?
O2 C1 1.325(3) . ?
O2 H2 0.8200 . ?
O3 C13 1.224(4) . ?
O4 C13 1.287(3) . ?
O5 C8 1.316(3) . ?
O5 H5 0.8200 . ?
O6 C8 1.236(3) . ?
N1 C16 1.494(4) . ?
N1 C19 1.532(5) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
C1 C2 1.528(4) . ?
C2 C3 1.543(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C14 1.411(4) . ?
C3 C4 1.419(3) . ?
C4 C6 1.415(3) . ?
C4 C5 1.529(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C9 1.415(3) . ?
C6 C7 1.531(3) . ?
C7 C8 1.515(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C11 1.411(3) . ?
C9 C10 1.530(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C14 1.420(4) . ?
C11 C12 1.526(3) . ?
C12 C13 1.542(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 C15 1.523(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.467(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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
C21A C20A C19 114.1(10) . . ?
C21B C20B C19 123.9(8) . . ?
C1 O2 H2 109.5 . . ?
C8 O5 H5 109.5 . . ?
C16 N1 C19 112.5(3) . . ?
C16 N1 H1A 109.1 . . ?
C19 N1 H1A 109.1 . . ?
C16 N1 H1B 109.1 . . ?
C19 N1 H1B 109.1 . . ?
H1A N1 H1B 107.8 . . ?
O1 C1 O2 123.5(3) . . ?
O1 C1 C2 123.8(3) . . ?
O2 C1 C2 112.8(2) . . ?
C1 C2 C3 112.6(2) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C14 C3 C4 121.3(2) . . ?
C14 C3 C2 119.6(2) . . ?
C4 C3 C2 119.1(2) . . ?
C6 C4 C3 118.6(2) . . ?
C6 C4 C5 119.6(2) . . ?
C3 C4 C5 121.8(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 C9 120.7(2) . . ?
C4 C6 C7 118.6(2) . . ?
C9 C6 C7 120.7(2) . . ?
C8 C7 C6 114.2(2) . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
O6 C8 O5 120.0(2) . . ?
O6 C8 C7 122.1(2) . . ?
O5 C8 C7 117.8(2) . . ?
C11 C9 C6 120.0(2) . . ?
C11 C9 C10 120.4(2) . . ?
C6 C9 C10 119.6(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 C14 120.0(2) . . ?
C9 C11 C12 119.9(2) . . ?
C14 C11 C12 120.1(2) . . ?
C11 C12 C13 115.6(2) . . ?
C11 C12 H12A 108.4 . . ?
C13 C12 H12A 108.4 . . ?
C11 C12 H12B 108.4 . . ?
C13 C12 H12B 108.4 . . ?
H12A C12 H12B 107.4 . . ?
O3 C13 O4 122.4(3) . . ?
O3 C13 C12 121.9(2) . . ?
O4 C13 C12 115.6(2) . . ?
C3 C14 C11 119.3(2) . . ?
C3 C14 C15 121.2(2) . . ?
C11 C14 C15 119.5(2) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 N1 111.9(3) . . ?
C17 C16 H16A 109.2 . . ?
N1 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
N1 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C18B C17 C18A 69.6(12) . . ?
C18B C17 C16 140.0(14) . . ?
C18A C17 C16 130.2(5) . . ?
C20B C19 N1 112.7(3) . . ?
N1 C19 C20A 103.0(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
O2 H2 O4 0.82 1.81 2.622(3) 172.4 4_556
O5 H5 O4 0.82 1.72 2.540(3) 173.6 1_565
N1 H1A O3 0.90 1.84 2.735(4) 179.3 1_565
N1 H1B O6 0.90 1.93 2.816(3) 166.9 2_655

_diffrn_measured_fraction_theta_max 0.681
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.681
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.049
# start Validation Reply Form
_vrf_PLAT029_tapas               
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.681 Note  
RESPONSE: The crystal was poorly diffracting and the data completeness
problem could not be resolved even after collecting several fresh data 
sets.
;
_vrf_PLAT043_tapas               
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..       8.07 Check  
RESPONSE: It was not possible to locate eight hydrogen atoms of the disordered 
cationic moity and as a result the calculated and reported molecular weight
differ by 8.07.
;
_database_code_depnum_ccdc_archive 'CCDC 929281'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_tapas

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H23 O6, C12 H24 N, H2 O'
_chemical_formula_sum            'C30 H49 N O7'
_chemical_formula_weight         535.70

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

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   17.7425(9)
_cell_length_b                   8.7392(5)
_cell_length_c                   19.5395(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.293(2)
_cell_angle_gamma                90.00
_cell_volume                     2960.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9473
_exptl_absorpt_correction_T_max  0.9809
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 CCD AREA DETECTOR'
_diffrn_measurement_method       'PHI-OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50741
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.41
_diffrn_reflns_theta_max         27.50
_reflns_number_total             6795
_reflns_number_gt                5693
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER APEX II'
_computing_cell_refinement       'BRUKER APEX II'
_computing_data_reduction        'BRUKER APEX II'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'MERCURY 2.3, PLATON'
_computing_publication_material  'MERCURY 2.3, PLATON'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0727P)²+0.8200P] where P=(Fo²+2Fc²)/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         6795
_refine_ls_number_parameters     356
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1297
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
O1 O 0.72993(7) 0.60940(17) 0.11302(6) 0.0657(4) Uani 1 1 d . . .
O2 O 0.73958(6) 0.48556(15) 0.01682(5) 0.0491(3) Uani 1 1 d . . .
H2 H 0.6952 0.5158 0.0032 0.074 Uiso 1 1 calc R . .
O6 O 1.10493(5) 0.99708(10) 0.30789(6) 0.0381(2) Uani 1 1 d . . .
H6 H 1.0739 1.0586 0.3176 0.057 Uiso 1 1 calc R . .
O5 O 1.10807(5) 0.75559(10) 0.27915(6) 0.0368(2) Uani 1 1 d . . .
O4 O 1.02927(5) 0.22680(10) 0.33869(5) 0.0341(2) Uani 1 1 d . . .
O3 O 0.97548(6) 0.11139(11) 0.41635(5) 0.0385(2) Uani 1 1 d . . .
O7 O 0.59906(6) 0.57367(12) 0.97553(5) 0.0369(2) Uani 1 1 d . . .
N1 N 0.12995(6) 0.44050(11) 0.30449(6) 0.0274(2) Uani 1 1 d . . .
H1A H 0.0954 0.3842 0.3213 0.033 Uiso 1 1 calc R . .
H1B H 0.1090 0.5336 0.2941 0.033 Uiso 1 1 calc R . .
C1 C 0.76622(7) 0.53360(15) 0.08089(7) 0.0312(3) Uani 1 1 d . . .
C2 C 0.84854(7) 0.48173(16) 0.10808(7) 0.0324(3) Uani 1 1 d . . .
H2A H 0.8508 0.3715 0.1029 0.039 Uiso 1 1 calc R . .
H2B H 0.8808 0.5269 0.0791 0.039 Uiso 1 1 calc R . .
C3 C 0.88172(6) 0.52242(14) 0.18374(6) 0.0255(2) Uani 1 1 d . . .
C4 C 0.88258(6) 0.41374(13) 0.23671(6) 0.0258(2) Uani 1 1 d . . .
C5 C 0.84798(9) 0.25559(16) 0.22019(8) 0.0439(3) Uani 1 1 d . . .
H5A H 0.8733 0.1844 0.2558 0.053 Uiso 1 1 calc R . .
H5B H 0.8578 0.2218 0.1756 0.053 Uiso 1 1 calc R . .
C6 C 0.76130(11) 0.2516(3) 0.21681(12) 0.0773(7) Uani 1 1 d . . .
H6A H 0.7512 0.2836 0.2610 0.116 Uiso 1 1 calc R . .
H6B H 0.7425 0.1494 0.2067 0.116 Uiso 1 1 calc R . .
H6C H 0.7357 0.3195 0.1806 0.116 Uiso 1 1 calc R . .
C7 C 0.91427(6) 0.45247(13) 0.30654(6) 0.0230(2) Uani 1 1 d . . .
C8 C 0.91336(7) 0.33574(14) 0.36380(6) 0.0277(2) Uani 1 1 d . . .
H8A H 0.8641 0.2830 0.3534 0.033 Uiso 1 1 calc R . .
H8B H 0.9166 0.3900 0.4076 0.033 Uiso 1 1 calc R . .
C9 C 0.97733(6) 0.21643(13) 0.37413(6) 0.0244(2) Uani 1 1 d . . .
C10 C 0.94726(6) 0.59715(13) 0.32300(6) 0.0226(2) Uani 1 1 d . . .
C11 C 0.97813(7) 0.64046(15) 0.39884(6) 0.0311(3) Uani 1 1 d . . .
H11A H 1.0189 0.7155 0.4014 0.037 Uiso 1 1 calc R . .
H11B H 1.0001 0.5506 0.4248 0.037 Uiso 1 1 calc R . .
C12 C 0.91491(9) 0.70647(18) 0.43244(7) 0.0417(3) Uani 1 1 d . . .
H12A H 0.8964 0.8006 0.4096 0.063 Uiso 1 1 calc R . .
H12B H 0.9355 0.7255 0.4812 0.063 Uiso 1 1 calc R . .
H12C H 0.8731 0.6347 0.4276 0.063 Uiso 1 1 calc R . .
C13 C 0.94737(6) 0.70473(12) 0.26958(6) 0.0239(2) Uani 1 1 d . . .
C14 C 0.98435(7) 0.85987(13) 0.28821(7) 0.0285(3) Uani 1 1 d . . .
H14A H 0.9750 0.8910 0.3333 0.034 Uiso 1 1 calc R . .
H14B H 0.9594 0.9339 0.2538 0.034 Uiso 1 1 calc R . .
C15 C 1.07053(7) 0.86453(13) 0.29156(6) 0.0269(2) Uani 1 1 d . . .
C16 C 0.91320(6) 0.66895(13) 0.19997(6) 0.0260(2) Uani 1 1 d . . .
C17 C 0.90911(9) 0.78709(17) 0.14205(8) 0.0404(3) Uani 1 1 d . . .
H17A H 0.9007 0.8871 0.1606 0.048 Uiso 1 1 calc R . .
H17B H 0.8649 0.7642 0.1049 0.048 Uiso 1 1 calc R . .
C18 C 0.98103(11) 0.7944(3) 0.11068(10) 0.0634(5) Uani 1 1 d . . .
H18A H 1.0251 0.8189 0.1468 0.095 Uiso 1 1 calc R . .
H18B H 0.9742 0.8718 0.0750 0.095 Uiso 1 1 calc R . .
H18C H 0.9888 0.6971 0.0905 0.095 Uiso 1 1 calc R . .
C19 C 0.14037(7) 0.36779(14) 0.23726(6) 0.0286(3) Uani 1 1 d . . .
H19 H 0.1616 0.2648 0.2476 0.034 Uiso 1 1 calc R . .
C20 C 0.06135(8) 0.35449(19) 0.18867(8) 0.0417(3) Uani 1 1 d . . .
H20A H 0.0381 0.4551 0.1810 0.050 Uiso 1 1 calc R . .
H20B H 0.0283 0.2909 0.2105 0.050 Uiso 1 1 calc R . .
C21 C 0.06768(10) 0.2849(2) 0.11854(9) 0.0538(4) Uani 1 1 d . . .
H21A H 0.0863 0.1805 0.1257 0.065 Uiso 1 1 calc R . .
H21B H 0.0170 0.2822 0.0877 0.065 Uiso 1 1 calc R . .
C22 C 0.12233(10) 0.3771(2) 0.08437(8) 0.0523(4) Uani 1 1 d . . .
H22A H 0.1279 0.3270 0.0414 0.063 Uiso 1 1 calc R . .
H22B H 0.1009 0.4781 0.0724 0.063 Uiso 1 1 calc R . .
C23 C 0.20065(9) 0.39205(19) 0.13299(8) 0.0441(3) Uani 1 1 d . . .
H23A H 0.2332 0.4567 0.1112 0.053 Uiso 1 1 calc R . .
H23B H 0.2246 0.2919 0.1402 0.053 Uiso 1 1 calc R . .
C24 C 0.19545(9) 0.45995(16) 0.20364(8) 0.0397(3) Uani 1 1 d . . .
H24A H 0.2462 0.4604 0.2343 0.048 Uiso 1 1 calc R . .
H24B H 0.1776 0.5649 0.1973 0.048 Uiso 1 1 calc R . .
C25 C 0.20047(7) 0.45940(14) 0.36230(7) 0.0299(3) Uani 1 1 d . . .
H25 H 0.2364 0.5283 0.3458 0.036 Uiso 1 1 calc R . .
C26 C 0.24128(9) 0.30821(17) 0.38277(9) 0.0442(3) Uani 1 1 d . . .
H26A H 0.2581 0.2652 0.3427 0.053 Uiso 1 1 calc R . .
H26B H 0.2058 0.2365 0.3971 0.053 Uiso 1 1 calc R . .
C27 C 0.31098(9) 0.3325(2) 0.44287(9) 0.0529(4) Uani 1 1 d . . .
H27A H 0.3353 0.2345 0.4566 0.063 Uiso 1 1 calc R . .
H27B H 0.3483 0.3969 0.4269 0.063 Uiso 1 1 calc R . .
C28 C 0.28841(10) 0.40617(19) 0.50570(9) 0.0486(4) Uani 1 1 d . . .
H28A H 0.3344 0.4259 0.5415 0.058 Uiso 1 1 calc R . .
H28B H 0.2558 0.3366 0.5251 0.058 Uiso 1 1 calc R . .
C29 C 0.24565(10) 0.55500(18) 0.48547(8) 0.0466(4) Uani 1 1 d . . .
H29A H 0.2806 0.6291 0.4722 0.056 Uiso 1 1 calc R . .
H29B H 0.2281 0.5953 0.5256 0.056 Uiso 1 1 calc R . .
C30 C 0.17674(9) 0.53337(16) 0.42506(8) 0.0384(3) Uani 1 1 d . . .
H30A H 0.1532 0.6320 0.4114 0.046 Uiso 1 1 calc R . .
H30B H 0.1387 0.4695 0.4402 0.046 Uiso 1 1 calc R . .
H7A H 0.5644(12) 0.505(2) 0.9521(11) 0.060(5) Uiso 1 1 d . . .
H7B H 0.5812(13) 0.601(2) 1.0134(12) 0.071(6) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.1914(17) . ?
O2 C1 1.3096(16) . ?
O6 C15 1.3165(14) . ?
O5 C15 1.2155(15) . ?
O4 C9 1.2682(15) . ?
O3 C9 1.2393(14) . ?
N1 C19 1.5056(15) . ?
N1 C25 1.5056(17) . ?
C1 C2 1.5134(17) . ?
C2 C3 1.5126(17) . ?
C3 C4 1.4025(17) . ?
C3 C16 1.4060(17) . ?
C4 C7 1.4021(17) . ?
C4 C5 1.5188(17) . ?
C5 C6 1.525(3) . ?
C7 C10 1.4017(15) . ?
C7 C8 1.5168(16) . ?
C8 C9 1.5227(16) . ?
C10 C13 1.4052(16) . ?
C10 C11 1.5144(16) . ?
C11 C12 1.5283(19) . ?
C13 C16 1.4014(17) . ?
C13 C14 1.5164(15) . ?
C14 C15 1.5171(16) . ?
C16 C17 1.5222(17) . ?
C17 C18 1.530(2) . ?
C19 C24 1.5193(17) . ?
C19 C20 1.5211(19) . ?
C20 C21 1.525(2) . ?
C21 C22 1.520(2) . ?
C22 C23 1.513(2) . ?
C23 C24 1.523(2) . ?
C25 C26 1.5187(18) . ?
C25 C30 1.5227(18) . ?
C26 C27 1.528(2) . ?
C27 C28 1.514(2) . ?
C28 C29 1.515(2) . ?
C29 C30 1.520(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 N1 C25 117.65(9) . . ?
O1 C1 O2 123.81(12) . . ?
O1 C1 C2 124.82(12) . . ?
O2 C1 C2 111.37(11) . . ?
C3 C2 C1 114.73(10) . . ?
C4 C3 C16 120.59(11) . . ?
C4 C3 C2 120.19(11) . . ?
C16 C3 C2 119.20(11) . . ?
C7 C4 C3 119.59(10) . . ?
C7 C4 C5 119.12(11) . . ?
C3 C4 C5 121.27(11) . . ?
C4 C5 C6 112.83(14) . . ?
C10 C7 C4 120.17(10) . . ?
C10 C7 C8 120.46(10) . . ?
C4 C7 C8 119.37(10) . . ?
C7 C8 C9 115.70(9) . . ?
O3 C9 O4 122.80(11) . . ?
O3 C9 C8 118.09(10) . . ?
O4 C9 C8 119.11(10) . . ?
C7 C10 C13 119.97(10) . . ?
C7 C10 C11 119.76(10) . . ?
C13 C10 C11 120.15(10) . . ?
C10 C11 C12 111.66(10) . . ?
C16 C13 C10 120.20(10) . . ?
C16 C13 C14 120.54(10) . . ?
C10 C13 C14 119.26(10) . . ?
C13 C14 C15 114.51(9) . . ?
O5 C15 O6 119.47(11) . . ?
O5 C15 C14 124.09(10) . . ?
O6 C15 C14 116.43(10) . . ?
C13 C16 C3 119.42(10) . . ?
C13 C16 C17 120.83(11) . . ?
C3 C16 C17 119.75(11) . . ?
C16 C17 C18 114.48(12) . . ?
N1 C19 C24 111.30(10) . . ?
N1 C19 C20 107.98(10) . . ?
C24 C19 C20 111.27(11) . . ?
C19 C20 C21 110.91(12) . . ?
C22 C21 C20 111.05(14) . . ?
C23 C22 C21 110.89(13) . . ?
C22 C23 C24 112.21(12) . . ?
C19 C24 C23 110.73(12) . . ?
N1 C25 C26 112.06(10) . . ?
N1 C25 C30 108.83(10) . . ?
C26 C25 C30 110.82(12) . . ?
C25 C26 C27 110.13(12) . . ?
C28 C27 C26 111.82(13) . . ?
C27 C28 C29 110.97(13) . . ?
C28 C29 C30 111.80(13) . . ?
C29 C30 C25 111.32(12) . . ?

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
O7 H7B O3 0.90(2) 1.87(2) 2.7407(14) 164(2) 2_656
O7 H7A O3 0.91(2) 1.88(2) 2.7713(14) 165.1(18) 4_566
N1 H1B O5 0.90 1.96 2.8101(13) 156.6 1_455
N1 H1A O4 0.90 1.89 2.7630(13) 164.2 1_455
O6 H6 O4 0.82 1.76 2.5572(12) 163.6 1_565
O2 H2 O7 0.82 1.75 2.5698(14) 177.7 1_554

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 929282'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_tapas1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H23 O6, C8 H26 N'
_chemical_formula_sum            'C26 H43 N O6'
_chemical_formula_weight         461.58

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

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

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

_cell_length_a                   31.663(3)
_cell_length_b                   10.0805(10)
_cell_length_c                   16.7716(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.662(2)
_cell_angle_gamma                90.00
_cell_volume                     5178.8(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.33
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2000
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9675
_exptl_absorpt_correction_T_max  0.9731
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 CCD AREA DETECTOR'
_diffrn_measurement_method       'PHI-OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30072
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         0.66
_diffrn_reflns_theta_max         20.18
_reflns_number_total             4950
_reflns_number_gt                3719
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER APEX II'
_computing_cell_refinement       'BRUKER APEX II'
_computing_data_reduction        'BRUKER APEX II'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'MERCURY 2.3, PLATON'
_computing_publication_material  'MERCURY 2.3, PLATON'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0779P)²+2.5946P] where P=(Fo²+2Fc²)/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         4950
_refine_ls_number_parameters     609
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1474
_refine_ls_wR_factor_gt          0.1327
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.31216(9) 0.4631(3) 0.89628(17) 0.0643(8) Uani 1 1 d . . .
H1 H 0.3306 0.4647 0.9405 0.096 Uiso 1 1 calc R . .
O2 O 0.35343(11) 0.6204(3) 0.86703(17) 0.0792(10) Uani 1 1 d . . .
O3 O 0.40414(9) 0.2015(3) 0.62887(18) 0.0602(8) Uani 1 1 d . . .
O4 O 0.36801(8) 0.0514(2) 0.54241(15) 0.0466(7) Uani 1 1 d . . .
O5 O 0.42990(8) 0.8847(2) 0.59584(17) 0.0535(8) Uani 1 1 d . . .
H5 H 0.4093 0.9347 0.5776 0.080 Uiso 1 1 calc R . .
O6 O 0.44110(8) 0.6762(3) 0.62844(17) 0.0546(8) Uani 1 1 d . . .
N1 N 0.45027(9) 0.4222(3) 0.70131(19) 0.0450(8) Uani 1 1 d . . .
H1A H 0.4419 0.4857 0.6628 0.054 Uiso 1 1 calc R . .
H1B H 0.4353 0.3479 0.6825 0.054 Uiso 1 1 calc R . .
C1 C 0.32264(14) 0.5482(4) 0.8459(2) 0.0437(10) Uani 1 1 d . . .
C2 C 0.29150(11) 0.5502(4) 0.7619(2) 0.0407(10) Uani 1 1 d . . .
H2A H 0.2762 0.6343 0.7543 0.049 Uiso 1 1 calc R . .
H2B H 0.2700 0.4807 0.7591 0.049 Uiso 1 1 calc R . .
C3 C 0.31342(11) 0.5308(3) 0.6913(2) 0.0330(9) Uani 1 1 d . . .
C4 C 0.31546(11) 0.4032(3) 0.6593(2) 0.0337(9) Uani 1 1 d . . .
C5 C 0.29896(12) 0.2846(4) 0.6975(2) 0.0454(10) Uani 1 1 d . . .
H5A H 0.3030 0.3008 0.7559 0.055 Uiso 1 1 calc R . .
H5B H 0.3163 0.2076 0.6916 0.055 Uiso 1 1 calc R . .
C6 C 0.25115(13) 0.2541(4) 0.6590(3) 0.0625(12) Uani 1 1 d . . .
H6A H 0.2333 0.3225 0.6735 0.094 Uiso 1 1 calc R . .
H6B H 0.2438 0.1703 0.6790 0.094 Uiso 1 1 calc R . .
H6C H 0.2461 0.2504 0.6001 0.094 Uiso 1 1 calc R . .
C7 C 0.33261(11) 0.3866(3) 0.5905(2) 0.0323(9) Uani 1 1 d . . .
C8 C 0.33118(12) 0.2510(3) 0.5508(2) 0.0389(10) Uani 1 1 d . . .
H8A H 0.3067 0.2028 0.5616 0.047 Uiso 1 1 calc R . .
H8B H 0.3252 0.2635 0.4917 0.047 Uiso 1 1 calc R . .
C9 C 0.37126(13) 0.1645(4) 0.5772(2) 0.0368(10) Uani 1 1 d . . .
C10 C 0.35009(11) 0.4937(3) 0.5577(2) 0.0318(9) Uani 1 1 d . . .
C11 C 0.36919(12) 0.4738(4) 0.4841(2) 0.0429(10) Uani 1 1 d . . .
H11A H 0.3808 0.3844 0.4860 0.051 Uiso 1 1 calc R . .
H11B H 0.3933 0.5350 0.4885 0.051 Uiso 1 1 calc R . .
C12 C 0.33627(13) 0.4947(4) 0.4009(2) 0.0564(12) Uani 1 1 d . . .
H12A H 0.3120 0.4357 0.3964 0.085 Uiso 1 1 calc R . .
H12B H 0.3501 0.4768 0.3572 0.085 Uiso 1 1 calc R . .
H12C H 0.3261 0.5848 0.3969 0.085 Uiso 1 1 calc R . .
C13 C 0.34914(11) 0.6201(3) 0.5917(2) 0.0320(9) Uani 1 1 d . . .
C14 C 0.36833(11) 0.7376(3) 0.5568(2) 0.0383(10) Uani 1 1 d . . .
H14A H 0.3651 0.7228 0.4984 0.046 Uiso 1 1 calc R . .
H14B H 0.3517 0.8163 0.5623 0.046 Uiso 1 1 calc R . .
C15 C 0.41552(13) 0.7630(4) 0.5972(2) 0.0389(10) Uani 1 1 d . . .
C16 C 0.33064(11) 0.6400(3) 0.6583(2) 0.0308(9) Uani 1 1 d . . .
C17 C 0.32877(12) 0.7777(3) 0.6929(2) 0.0434(10) Uani 1 1 d . . .
H17A H 0.3542 0.8272 0.6875 0.052 Uiso 1 1 calc R . .
H17B H 0.3302 0.7707 0.7512 0.052 Uiso 1 1 calc R . .
C18 C 0.28807(14) 0.8540(4) 0.6508(3) 0.0674(13) Uani 1 1 d . . .
H18A H 0.2881 0.8704 0.5944 0.101 Uiso 1 1 calc R . .
H18B H 0.2876 0.9370 0.6786 0.101 Uiso 1 1 calc R . .
H18C H 0.2627 0.8031 0.6526 0.101 Uiso 1 1 calc R . .
C19 C 0.43904(14) 0.4652(4) 0.7787(3) 0.0580(12) Uani 1 1 d . . .
H19A H 0.4082 0.4863 0.7655 0.070 Uiso 1 1 calc R . .
H19B H 0.4549 0.5461 0.7978 0.070 Uiso 1 1 calc R . .
C20 C 0.44861(14) 0.3663(4) 0.8481(3) 0.0595(12) Uani 1 1 d . . .
H20 H 0.4784 0.3333 0.8552 0.071 Uiso 1 1 calc R . .
C21 C 0.4180(2) 0.2512(6) 0.8308(3) 0.128(3) Uani 1 1 d . . .
H21A H 0.3885 0.2826 0.8206 0.192 Uiso 1 1 calc R . .
H21B H 0.4241 0.1926 0.8774 0.192 Uiso 1 1 calc R . .
H21C H 0.4217 0.2045 0.7832 0.192 Uiso 1 1 calc R . .
C22 C 0.4458(2) 0.4356(6) 0.9264(3) 0.117(2) Uani 1 1 d . . .
H22A H 0.4172 0.4730 0.9191 0.176 Uiso 1 1 calc R . .
H22B H 0.4673 0.5050 0.9389 0.176 Uiso 1 1 calc R . .
H22C H 0.4512 0.3728 0.9709 0.176 Uiso 1 1 calc R . .
C23 C 0.49806(13) 0.3961(4) 0.7134(3) 0.0653(13) Uani 1 1 d . A .
H23A H 0.5141 0.4720 0.7412 0.078 Uiso 1 1 calc R . .
H23B H 0.5060 0.3202 0.7497 0.078 Uiso 1 1 calc R . .
C24 C 0.51231(17) 0.3705(8) 0.6381(3) 0.128(3) Uani 1 1 d D . .
C25A C 0.4939(4) 0.4125(12) 0.5535(7) 0.092(3) Uiso 0.48 1 d PD A 1
C25B C 0.4908(3) 0.3056(11) 0.5744(7) 0.086(3) Uiso 0.52 1 d P A 2
C26 C 0.56165(17) 0.3502(7) 0.6614(4) 0.133(3) Uani 1 1 d . A .
H26A H 0.5715 0.3359 0.6124 0.199 Uiso 1 1 calc R . .
H26B H 0.5689 0.2743 0.6968 0.199 Uiso 1 1 calc R . .
H26C H 0.5757 0.4275 0.6895 0.199 Uiso 1 1 calc R . .
O1' O 0.18402(9) -0.0337(3) 0.57399(19) 0.0638(8) Uani 1 1 d . . .
H1' H 0.1662 -0.0263 0.6016 0.096 Uiso 1 1 calc R . .
O2' O 0.14619(11) 0.1303(3) 0.50707(19) 0.0784(10) Uani 1 1 d . . .
O3' O 0.09453(9) -0.3087(3) 0.22272(18) 0.0580(8) Uani 1 1 d . . .
O4' O 0.13054(8) -0.4584(2) 0.17003(15) 0.0451(7) Uani 1 1 d . . .
O5' O 0.07017(8) 0.3715(2) 0.16091(18) 0.0534(8) Uani 1 1 d . . .
H5' H 0.0908 0.4223 0.1647 0.080 Uiso 1 1 calc R . .
O6' O 0.05923(8) 0.1628(3) 0.18028(17) 0.0565(8) Uani 1 1 d . . .
N1' N 0.04829(9) 0.5843(3) 0.74857(18) 0.0433(8) Uani 1 1 d . . .
H1'1 H 0.0569 0.5228 0.7171 0.052 Uiso 1 1 calc R . .
H1'2 H 0.0630 0.6595 0.7451 0.052 Uiso 1 1 calc R . .
C1' C 0.17558(13) 0.0533(4) 0.5147(2) 0.0404(10) Uani 1 1 d . . .
C2' C 0.20678(11) 0.0501(4) 0.4605(2) 0.0380(10) Uani 1 1 d . . .
H2'1 H 0.2282 -0.0191 0.4802 0.046 Uiso 1 1 calc R . .
H2'2 H 0.2223 0.1340 0.4659 0.046 Uiso 1 1 calc R . .
C3' C 0.18544(11) 0.0256(3) 0.3697(2) 0.0312(9) Uani 1 1 d . . .
C4' C 0.18315(11) -0.1044(3) 0.3387(2) 0.0323(9) Uani 1 1 d . . .
C5' C 0.19717(11) -0.2209(3) 0.3965(2) 0.0418(10) Uani 1 1 d . . .
H5'1 H 0.1789 -0.2965 0.3748 0.050 Uiso 1 1 calc R . .
H5'2 H 0.1920 -0.1988 0.4495 0.050 Uiso 1 1 calc R . .
C6' C 0.24498(12) -0.2618(4) 0.4099(3) 0.0558(12) Uani 1 1 d . . .
H6'1 H 0.2499 -0.2925 0.3588 0.084 Uiso 1 1 calc R . .
H6'2 H 0.2516 -0.3317 0.4500 0.084 Uiso 1 1 calc R . .
H6'3 H 0.2635 -0.1869 0.4293 0.084 Uiso 1 1 calc R . .
C7' C 0.16705(11) -0.1258(3) 0.2543(2) 0.0324(9) Uani 1 1 d . . .
C8' C 0.16836(12) -0.2628(3) 0.2187(2) 0.0405(10) Uani 1 1 d . . .
H8'1 H 0.1917 -0.3117 0.2555 0.049 Uiso 1 1 calc R . .
H8'2 H 0.1761 -0.2535 0.1667 0.049 Uiso 1 1 calc R . .
C9' C 0.12728(13) -0.3466(4) 0.2037(2) 0.0361(9) Uani 1 1 d . . .
C10' C 0.15042(11) -0.0196(3) 0.2015(2) 0.0327(9) Uani 1 1 d . . .
C11' C 0.13263(12) -0.0438(4) 0.1096(2) 0.0459(10) Uani 1 1 d . . .
H11C H 0.1086 0.0167 0.0886 0.055 Uiso 1 1 calc R . .
H11D H 0.1211 -0.1334 0.1014 0.055 Uiso 1 1 calc R . .
C12' C 0.16626(15) -0.0262(4) 0.0596(3) 0.0664(13) Uani 1 1 d . . .
H12D H 0.1757 0.0645 0.0627 0.100 Uiso 1 1 calc R . .
H12E H 0.1534 -0.0493 0.0031 0.100 Uiso 1 1 calc R . .
H12F H 0.1909 -0.0828 0.0815 0.100 Uiso 1 1 calc R . .
C13' C 0.15092(11) 0.1085(3) 0.2338(2) 0.0315(9) Uani 1 1 d . . .
C14' C 0.13190(11) 0.2241(3) 0.1783(2) 0.0367(9) Uani 1 1 d . . .
H14C H 0.1486 0.3034 0.1984 0.044 Uiso 1 1 calc R . .
H14D H 0.1349 0.2064 0.1232 0.044 Uiso 1 1 calc R . .
C15' C 0.08470(13) 0.2495(4) 0.1741(2) 0.0380(10) Uani 1 1 d . . .
C16' C 0.16908(10) 0.1322(3) 0.3178(2) 0.0288(9) Uani 1 1 d . . .
C17' C 0.17111(12) 0.2713(3) 0.3522(2) 0.0420(10) Uani 1 1 d . . .
H17C H 0.1684 0.2668 0.4085 0.050 Uiso 1 1 calc R . .
H17D H 0.1464 0.3215 0.3203 0.050 Uiso 1 1 calc R . .
C18' C 0.21283(14) 0.3449(4) 0.3516(3) 0.0681(13) Uani 1 1 d . . .
H18D H 0.2375 0.2908 0.3770 0.102 Uiso 1 1 calc R . .
H18E H 0.2140 0.4264 0.3817 0.102 Uiso 1 1 calc R . .
H18F H 0.2133 0.3639 0.2958 0.102 Uiso 1 1 calc R . .
C19' C 0.05984(14) 0.5382(4) 0.8354(3) 0.0555(12) Uani 1 1 d . . .
H19C H 0.0909 0.5201 0.8517 0.067 Uiso 1 1 calc R . .
H19D H 0.0448 0.4552 0.8382 0.067 Uiso 1 1 calc R . .
C20' C 0.04908(14) 0.6331(4) 0.8971(2) 0.0547(11) Uani 1 1 d . . .
H20' H 0.0185 0.6604 0.8774 0.066 Uiso 1 1 calc R . .
C21' C 0.0549(2) 0.5615(6) 0.9790(3) 0.118(2) Uani 1 1 d . . .
H21D H 0.0837 0.5242 0.9954 0.177 Uiso 1 1 calc R . .
H21E H 0.0337 0.4918 0.9732 0.177 Uiso 1 1 calc R . .
H21F H 0.0510 0.6232 1.0202 0.177 Uiso 1 1 calc R . .
C22' C 0.0772(2) 0.7534(6) 0.9082(4) 0.124(2) Uani 1 1 d . . .
H22D H 0.1073 0.7275 0.9250 0.186 Uiso 1 1 calc R . .
H22E H 0.0704 0.8093 0.9496 0.186 Uiso 1 1 calc R . .
H22F H 0.0719 0.8010 0.8570 0.186 Uiso 1 1 calc R . .
C23' C 0.00066(13) 0.6095(4) 0.7153(3) 0.0626(13) Uani 1 1 d . B .
H23C H -0.0152 0.5341 0.7289 0.075 Uiso 1 1 calc R . .
H23D H -0.0072 0.6863 0.7432 0.075 Uiso 1 1 calc R . .
C24' C -0.01404(17) 0.6324(8) 0.6259(3) 0.129(3) Uani 1 1 d D . .
C25' C 0.0057(4) 0.5951(12) 0.5595(7) 0.091(3) Uiso 0.48 1 d PD B 1
C27' C 0.0077(3) 0.6996(11) 0.5821(7) 0.086(3) Uiso 0.52 1 d P B 2
C26' C -0.06336(16) 0.6500(7) 0.6027(3) 0.122(2) Uani 1 1 d . B .
H26D H -0.0708 0.7277 0.6292 0.183 Uiso 1 1 calc R . .
H26E H -0.0768 0.5736 0.6201 0.183 Uiso 1 1 calc R . .
H26F H -0.0736 0.6596 0.5440 0.183 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.305(4) . ?
O2 C1 1.196(4) . ?
O3 O3 0.000(8) 1 ?
O3 C9 1.232(4) . ?
O4 C9 1.273(4) . ?
O5 C15 1.311(4) . ?
O6 C15 1.218(4) . ?
N1 C19 1.493(5) . ?
N1 C23 1.498(5) . ?
C1 C2 1.501(5) . ?
C2 C3 1.528(5) . ?
C3 C4 1.402(5) . ?
C3 C16 1.403(5) . ?
C4 C7 1.405(5) . ?
C4 C5 1.510(5) . ?
C5 C6 1.519(5) . ?
C7 C10 1.389(5) . ?
C7 C8 1.515(5) . ?
C8 C9 1.511(5) . ?
C9 O3 1.232(4) 1 ?
C10 C13 1.399(5) . ?
C10 C11 1.519(5) . ?
C11 C12 1.531(5) . ?
C13 C16 1.401(5) . ?
C13 C14 1.516(5) . ?
C14 C15 1.498(5) . ?
C15 O6 1.218(4) 1 ?
C16 C17 1.511(5) . ?
C17 C18 1.513(5) . ?
C19 C20 1.504(6) . ?
C20 C21 1.493(6) . ?
C20 C22 1.509(6) . ?
C23 C24 1.468(7) . ?
C24 C25B 1.289(11) . ?
C24 C25A 1.454(11) . ?
C24 C26 1.525(7) . ?
O1' C1' 1.302(4) . ?
O2' C1' 1.193(4) . ?
O3' C9' 1.221(4) . ?
O4' C9' 1.276(4) . ?
O5' C15' 1.312(4) . ?
O6' C15' 1.212(4) . ?
N1' C19' 1.484(5) . ?
N1' C23' 1.491(5) . ?
C1' C2' 1.502(5) . ?
C2' C3' 1.522(5) . ?
C3' C16' 1.397(5) . ?
C3' C4' 1.405(5) . ?
C4' C7' 1.395(5) . ?
C4' C5' 1.516(5) . ?
C5' C6' 1.530(5) . ?
C7' C10' 1.404(5) . ?
C7' C8' 1.509(5) . ?
C8' C9' 1.518(5) . ?
C10' C13' 1.399(5) . ?
C10' C11' 1.521(5) . ?
C11' C12' 1.523(5) . ?
C13' C16' 1.401(5) . ?
C13' C14' 1.517(5) . ?
C14' C15' 1.500(5) . ?
C16' C17' 1.512(5) . ?
C17' C18' 1.517(5) . ?
C19' C20' 1.509(5) . ?
C20' C22' 1.487(6) . ?
C20' C21' 1.522(6) . ?
C23' C24' 1.470(6) . ?
C24' C27' 1.314(12) . ?
C24' C25' 1.459(11) . ?
C24' C26' 1.521(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


C19 N1 C23 112.8(3) . . ?
O2 C1 O1 122.0(4) . . ?
O2 C1 C2 124.2(4) . . ?
O1 C1 C2 113.7(4) . . ?
C1 C2 C3 113.9(3) . . ?
C4 C3 C16 120.6(3) . . ?
C4 C3 C2 119.2(3) . . ?
C16 C3 C2 120.2(3) . . ?
C3 C4 C7 119.3(3) . . ?
C3 C4 C5 120.6(3) . . ?
C7 C4 C5 120.1(3) . . ?
C4 C5 C6 113.2(3) . . ?
C10 C7 C4 120.5(3) . . ?
C10 C7 C8 119.9(3) . . ?
C4 C7 C8 119.5(3) . . ?
C9 C8 C7 117.6(3) . . ?
O3 C9 O4 123.4(3) 1 . ?
O3 C9 O4 123.4(3) . . ?
O3 C9 C8 121.9(3) 1 . ?
O3 C9 C8 121.9(3) . . ?
O4 C9 C8 114.7(3) . . ?
C7 C10 C13 119.7(3) . . ?
C7 C10 C11 119.9(3) . . ?
C13 C10 C11 120.4(3) . . ?
C10 C11 C12 113.8(3) . . ?
C10 C13 C16 120.8(3) . . ?
C10 C13 C14 120.1(3) . . ?
C16 C13 C14 119.1(3) . . ?
C15 C14 C13 114.2(3) . . ?
O6 C15 O5 119.0(3) 1 . ?
O6 C15 O5 119.0(3) . . ?
O6 C15 C14 123.4(3) 1 . ?
O6 C15 C14 123.4(3) . . ?
O5 C15 C14 117.6(3) . . ?
C13 C16 C3 119.0(3) . . ?
C13 C16 C17 120.1(3) . . ?
C3 C16 C17 120.8(3) . . ?
C16 C17 C18 113.5(3) . . ?
N1 C19 C20 115.8(3) . . ?
C21 C20 C19 111.7(4) . . ?
C21 C20 C22 110.5(5) . . ?
C19 C20 C22 108.8(4) . . ?
C24 C23 N1 115.7(4) . . ?
C25B C24 C25A 48.9(6) . . ?
C25B C24 C23 126.1(7) . . ?
C25A C24 C23 130.8(6) . . ?
C25B C24 C26 115.8(7) . . ?
C25A C24 C26 114.9(6) . . ?
C23 C24 C26 108.7(5) . . ?
C19' N1' C23' 113.3(3) . . ?
O2' C1' O1' 121.6(4) . . ?
O2' C1' C2' 124.3(4) . . ?
O1' C1' C2' 114.1(4) . . ?
C1' C2' C3' 114.5(3) . . ?
C16' C3' C4' 120.7(3) . . ?
C16' C3' C2' 120.0(3) . . ?
C4' C3' C2' 119.3(3) . . ?
C7' C4' C3' 119.4(3) . . ?
C7' C4' C5' 120.1(3) . . ?
C3' C4' C5' 120.4(3) . . ?
C4' C5' C6' 114.9(3) . . ?
C4' C7' C10' 120.3(3) . . ?
C4' C7' C8' 120.2(3) . . ?
C10' C7' C8' 119.5(3) . . ?
C7' C8' C9' 117.8(3) . . ?
O3' C9' O4' 124.1(3) . . ?
O3' C9' C8' 122.1(3) . . ?
O4' C9' C8' 113.8(3) . . ?
C13' C10' C7' 119.6(3) . . ?
C13' C10' C11' 120.4(3) . . ?
C7' C10' C11' 120.0(3) . . ?
C10' C11' C12' 114.1(3) . . ?
C10' C13' C16' 120.6(3) . . ?
C10' C13' C14' 120.5(3) . . ?
C16' C13' C14' 118.9(3) . . ?
C15' C14' C13' 113.4(3) . . ?
O6' C15' O5' 118.6(3) . . ?
O6' C15' C14' 123.3(3) . . ?
O5' C15' C14' 118.1(3) . . ?
C3' C16' C13' 119.3(3) . . ?
C3' C16' C17' 120.1(3) . . ?
C13' C16' C17' 120.6(3) . . ?
C16' C17' C18' 113.8(3) . . ?
N1' C19' C20' 115.6(3) . . ?
C22' C20' C19' 111.8(4) . . ?
C22' C20' C21' 110.0(4) . . ?
C19' C20' C21' 108.7(4) . . ?
C24' C23' N1' 116.0(4) . . ?
C27' C24' C25' 47.1(6) . . ?
C27' C24' C23' 125.1(7) . . ?
C25' C24' C23' 130.7(6) . . ?
C27' C24' C26' 116.4(7) . . ?
C25' C24' C26' 116.4(6) . . ?
C23' C24' C26' 108.6(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
N1' H1'2 O3' 0.90 1.89 2.788(4) 171.7 4_566
N1' H1'1 O6' 0.90 1.98 2.800(4) 151.2 4_566
O5' H5' O4' 0.82 1.73 2.543(3) 174.3 1_565
O1' H1' O4' 0.82 1.81 2.617(4) 168.9 4_556
N1 H1B O3 0.90 1.87 2.768(4) 172.2 1
N1 H1A O6 0.90 2.00 2.820(4) 150.2 1
O5 H5 O4 0.82 1.75 2.564(3) 175.4 1_565
O1 H1 O4 0.82 1.82 2.638(4) 172.3 4_566

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        20.18
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.044
# start Validation Reply Form
_vrf_THETM01_tapas               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The crystal was poorly diffracting at higher Bragg angles 
and the problem could not be resolved even after low temperature 
fresh data collection on several crystals.
;
_database_code_depnum_ccdc_archive 'CCDC 929283'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_tapas

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H23 O6, C6 H12 N'
_chemical_formula_sum            'C24 H32 N O6'
_chemical_formula_weight         433.54

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   'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'

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

_cell_length_a                   16.681(2)
_cell_length_b                   10.1817(14)
_cell_length_c                   28.164(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4783.5(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.34
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1848
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9658
_exptl_absorpt_correction_T_max  0.9715
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 CCD AREA DETECTOR'
_diffrn_measurement_method       'PHI-OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29880
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         19.47
_reflns_number_total             4133
_reflns_number_gt                3822
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER APEX II'
_computing_cell_refinement       'BRUKER APEX II'
_computing_data_reduction        'BRUKER APEX II'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'MERCURY 2.3, PLATON'
_computing_publication_material  'MERCURY 2.3, PLATON'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0720P)²+1.7435P] where P=(Fo²+2Fc²)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_number_reflns         4133
_refine_ls_number_parameters     567
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      1.017
_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
C24' C 0.6821(5) 0.3669(8) 0.2037(3) 0.062(2) Uiso 0.64 1 d PD A 1
C21A C 0.5789(7) 0.1055(11) 0.3212(4) 0.064(3) Uiso 0.49 1 d PD B 1
C21B C 0.5211(9) 0.0262(15) 0.3365(6) 0.081(5) Uiso 0.51 1 d P B 2
C24" C 0.7380(12) 0.471(2) 0.1884(8) 0.075(6) Uiso 0.36 1 d P A 2
O1 O 0.61297(17) 0.2046(3) 0.44432(12) 0.0413(8) Uani 1 1 d . . .
H1 H 0.6495 0.2023 0.4249 0.062 Uiso 1 1 calc R . .
O2 O 0.56983(16) 0.3676(3) 0.39844(13) 0.0377(8) Uani 1 1 d . . .
O3 O 0.23395(18) -0.1867(3) 0.38527(11) 0.0399(9) Uani 1 1 d . . .
O4 O 0.3212(2) -0.0546(3) 0.35111(13) 0.0467(9) Uani 1 1 d . . .
O5 O 0.29988(18) 0.4522(3) 0.30638(11) 0.0360(8) Uani 1 1 d . . .
O6 O 0.26483(19) 0.6549(3) 0.31999(11) 0.0384(8) Uani 1 1 d . . .
H6 H 0.2544 0.7017 0.3429 0.058 Uiso 1 1 calc R . .
N1 N 0.3814(2) 0.1039(3) 0.28250(14) 0.0376(10) Uani 1 1 d . . .
H1A H 0.3581 0.0533 0.3048 0.045 Uiso 1 1 calc R . .
H1B H 0.4094 0.0508 0.2631 0.045 Uiso 1 1 calc R . .
C1 C 0.5617(2) 0.2974(5) 0.43238(18) 0.0260(11) Uani 1 1 d . . .
C2 C 0.4917(2) 0.3067(4) 0.46626(16) 0.0279(11) Uani 1 1 d . . .
H2A H 0.4932 0.3918 0.4817 0.033 Uiso 1 1 calc R . .
H2B H 0.4980 0.2403 0.4906 0.033 Uiso 1 1 calc R . .
C3 C 0.4100(2) 0.2894(4) 0.44301(15) 0.0233(11) Uani 1 1 d . . .
C4 C 0.3759(2) 0.1635(4) 0.44110(15) 0.0239(11) Uani 1 1 d . . .
C5 C 0.4201(2) 0.0446(4) 0.46013(17) 0.0316(12) Uani 1 1 d . . .
H5A H 0.4773 0.0574 0.4559 0.038 Uiso 1 1 calc R . .
H5B H 0.4045 -0.0322 0.4420 0.038 Uiso 1 1 calc R . .
C6 C 0.4027(3) 0.0201(5) 0.5129(2) 0.0429(15) Uani 1 1 d . . .
H6A H 0.4276 0.0875 0.5316 0.064 Uiso 1 1 calc R . .
H6B H 0.4238 -0.0640 0.5219 0.064 Uiso 1 1 calc R . .
H6C H 0.3459 0.0213 0.5181 0.064 Uiso 1 1 calc R . .
C7 C 0.2988(2) 0.1488(4) 0.42151(15) 0.0251(11) Uani 1 1 d . . .
C8 C 0.2582(3) 0.0145(4) 0.42335(19) 0.0276(13) Uani 1 1 d . . .
H8A H 0.2748 -0.0288 0.4524 0.033 Uiso 1 1 calc R . .
H8B H 0.2008 0.0286 0.4256 0.033 Uiso 1 1 calc R . .
C9 C 0.2733(3) -0.0781(4) 0.38284(18) 0.0296(12) Uani 1 1 d . . .
C10 C 0.2583(2) 0.2553(4) 0.40156(15) 0.0236(11) Uani 1 1 d . . .
C11 C 0.1776(2) 0.2363(4) 0.37736(16) 0.0316(12) Uani 1 1 d . . .
H11A H 0.1732 0.2987 0.3515 0.038 Uiso 1 1 calc R . .
H11B H 0.1758 0.1488 0.3638 0.038 Uiso 1 1 calc R . .
C12 C 0.1057(2) 0.2534(5) 0.40988(18) 0.0423(13) Uani 1 1 d . . .
H12A H 0.1085 0.1906 0.4352 0.063 Uiso 1 1 calc R . .
H12B H 0.0573 0.2399 0.3921 0.063 Uiso 1 1 calc R . .
H12C H 0.1059 0.3406 0.4228 0.063 Uiso 1 1 calc R . .
C13 C 0.2936(2) 0.3808(4) 0.40414(15) 0.0243(11) Uani 1 1 d . . .
C14 C 0.2507(3) 0.4991(4) 0.3841(2) 0.0287(13) Uani 1 1 d . . .
H14A H 0.1934 0.4831 0.3853 0.034 Uiso 1 1 calc R . .
H14B H 0.2619 0.5743 0.4042 0.034 Uiso 1 1 calc R . .
C15 C 0.2734(3) 0.5323(5) 0.33427(19) 0.0263(12) Uani 1 1 d . . .
C16 C 0.3697(2) 0.3985(4) 0.42396(14) 0.0215(11) Uani 1 1 d . . .
C17 C 0.4072(3) 0.5343(4) 0.42509(18) 0.0306(12) Uani 1 1 d . . .
H17A H 0.3892 0.5834 0.3976 0.037 Uiso 1 1 calc R . .
H17B H 0.4650 0.5256 0.4230 0.037 Uiso 1 1 calc R . .
C18 C 0.3862(3) 0.6115(4) 0.46993(19) 0.0439(13) Uani 1 1 d . . .
H18A H 0.3296 0.6289 0.4705 0.066 Uiso 1 1 calc R . .
H18B H 0.4151 0.6930 0.4701 0.066 Uiso 1 1 calc R . .
H18C H 0.4006 0.5610 0.4974 0.066 Uiso 1 1 calc R . .
C19 C 0.4378(3) 0.1959(5) 0.30617(18) 0.0489(14) Uani 1 1 d D B .
H19A H 0.4590 0.2570 0.2829 0.059 Uiso 1 1 calc R . .
H19B H 0.4092 0.2461 0.3300 0.059 Uiso 1 1 calc R . .
C20 C 0.5049(4) 0.1246(8) 0.3288(2) 0.084(2) Uani 1 1 d D . .
C22 C 0.3172(3) 0.1709(5) 0.25422(19) 0.0487(15) Uani 1 1 d . . .
H22A H 0.2834 0.2219 0.2754 0.058 Uiso 1 1 calc R . .
H22B H 0.3417 0.2309 0.2317 0.058 Uiso 1 1 calc R . .
C23 C 0.2671(4) 0.0738(5) 0.2281(2) 0.0619(17) Uani 1 1 d . . .
H23A H 0.2922 0.0243 0.2047 0.074 Uiso 1 1 calc R . .
C24 C 0.1929(5) 0.0526(7) 0.2351(3) 0.101(3) Uani 1 1 d . . .
H24A H 0.1654 0.1000 0.2582 0.122 Uiso 1 1 calc R . .
H24B H 0.1660 -0.0101 0.2172 0.122 Uiso 1 1 calc R . .
O1' O 1.02334(19) 0.7003(3) 0.13587(12) 0.0386(8) Uani 1 1 d . . .
H1' H 1.0100 0.7506 0.1572 0.058 Uiso 1 1 calc R . .
O2' O 0.9334(2) 0.5714(3) 0.17032(12) 0.0466(9) Uani 1 1 d . . .
O3' O 0.69138(17) 0.1186(3) 0.12148(12) 0.0404(9) Uani 1 1 d . . .
O4' O 0.64569(19) 0.2873(3) 0.07919(11) 0.0406(8) Uani 1 1 d . . .
H4' H 0.6068 0.2791 0.0968 0.061 Uiso 1 1 calc R . .
O5' O 0.99695(19) -0.1395(3) 0.20035(11) 0.0422(9) Uani 1 1 d . . .
O6' O 0.95954(18) 0.0622(3) 0.21435(12) 0.0374(8) Uani 1 1 d . . .
N1' N 0.8804(2) 0.3993(3) 0.23738(13) 0.0358(10) Uani 1 1 d . . .
H1'1 H 0.9013 0.4518 0.2149 0.043 Uiso 1 1 calc R . .
H1'2 H 0.8511 0.4498 0.2570 0.043 Uiso 1 1 calc R . .
C1' C 0.9808(3) 0.5943(4) 0.13830(18) 0.0276(11) Uani 1 1 d . . .
C2' C 0.9940(3) 0.5024(4) 0.0963(2) 0.0307(14) Uani 1 1 d . . .
H2'1 H 0.9735 0.5452 0.0681 0.037 Uiso 1 1 calc R . .
H2'2 H 1.0513 0.4913 0.0920 0.037 Uiso 1 1 calc R . .
C3' C 0.9563(2) 0.3672(4) 0.09948(16) 0.0269(12) Uani 1 1 d . . .
C4' C 0.8793(2) 0.3461(4) 0.08095(15) 0.0242(11) Uani 1 1 d . . .
C5' C 0.8282(3) 0.4623(4) 0.06533(17) 0.0333(12) Uani 1 1 d . . .
H5'1 H 0.8421 0.5373 0.0849 0.040 Uiso 1 1 calc R . .
H5'2 H 0.7725 0.4415 0.0715 0.040 Uiso 1 1 calc R . .
C6' C 0.8363(3) 0.5026(4) 0.01294(19) 0.0372(14) Uani 1 1 d . . .
H6'1 H 0.8903 0.5304 0.0068 0.056 Uiso 1 1 calc R . .
H6'2 H 0.8001 0.5736 0.0063 0.056 Uiso 1 1 calc R . .
H6'3 H 0.8235 0.4291 -0.0070 0.056 Uiso 1 1 calc R . .
C7' C 0.8491(2) 0.2183(4) 0.07817(14) 0.0226(11) Uani 1 1 d . . .
C8' C 0.7682(2) 0.1942(4) 0.05468(16) 0.0269(11) Uani 1 1 d . . .
H8'1 H 0.7591 0.2616 0.0310 0.032 Uiso 1 1 calc R . .
H8'2 H 0.7698 0.1102 0.0385 0.032 Uiso 1 1 calc R . .
C9' C 0.6992(2) 0.1942(5) 0.08895(18) 0.0279(12) Uani 1 1 d . . .
C10' C 0.8934(2) 0.1117(4) 0.09648(15) 0.0219(11) Uani 1 1 d . . .
C11' C 0.8597(3) -0.0254(4) 0.09280(19) 0.0315(13) Uani 1 1 d . . .
H11C H 0.8017 -0.0207 0.0949 0.038 Uiso 1 1 calc R . .
H11D H 0.8786 -0.0764 0.1197 0.038 Uiso 1 1 calc R . .
C12' C 0.8823(3) -0.0972(4) 0.04719(18) 0.0436(13) Uani 1 1 d . . .
H12D H 0.8672 -0.0448 0.0203 0.065 Uiso 1 1 calc R . .
H12E H 0.8548 -0.1800 0.0460 0.065 Uiso 1 1 calc R . .
H12F H 0.9391 -0.1120 0.0466 0.065 Uiso 1 1 calc R . .
C13' C 0.9685(2) 0.1346(4) 0.11707(14) 0.0217(11) Uani 1 1 d . . .
C14' C 1.0146(3) 0.0194(4) 0.13715(19) 0.0246(12) Uani 1 1 d . . .
H14C H 1.0076 -0.0557 0.1164 0.029 Uiso 1 1 calc R . .
H14D H 1.0712 0.0411 0.1377 0.029 Uiso 1 1 calc R . .
C15' C 0.9883(3) -0.0176(5) 0.1864(2) 0.0313(13) Uani 1 1 d . . .
C16' C 0.9998(2) 0.2626(4) 0.11890(15) 0.0263(12) Uani 1 1 d . . .
C17' C 1.0799(2) 0.2886(4) 0.14272(17) 0.0365(13) Uani 1 1 d . . .
H17C H 1.0856 0.2290 0.1694 0.044 Uiso 1 1 calc R . .
H17D H 1.0797 0.3773 0.1552 0.044 Uiso 1 1 calc R . .
C18' C 1.1536(3) 0.2723(5) 0.1098(2) 0.0541(16) Uani 1 1 d . . .
H18D H 1.1582 0.1821 0.1003 0.081 Uiso 1 1 calc R . .
H18E H 1.2012 0.2980 0.1266 0.081 Uiso 1 1 calc R . .
H18F H 1.1472 0.3266 0.0823 0.081 Uiso 1 1 calc R . .
C19' C 0.9469(3) 0.3390(5) 0.26477(18) 0.0445(14) Uani 1 1 d . . .
H19C H 0.9817 0.2915 0.2432 0.053 Uiso 1 1 calc R . .
H19D H 0.9249 0.2763 0.2872 0.053 Uiso 1 1 calc R . .
C20' C 0.9952(4) 0.4380(5) 0.2911(2) 0.0601(16) Uani 1 1 d . . .
H20' H 0.9687 0.4868 0.3142 0.072 Uiso 1 1 calc R . .
C21' C 1.0693(4) 0.4619(7) 0.2852(3) 0.0742(18) Uani 1 1 d . . .
H21A H 1.0983 0.4156 0.2625 0.089 Uiso 1 1 calc R . .
H21B H 1.0944 0.5259 0.3034 0.089 Uiso 1 1 calc R . .
C22' C 0.8266(3) 0.3010(5) 0.21425(18) 0.0464(14) Uani 1 1 d . A .
H22C H 0.8077 0.2383 0.2376 0.056 Uiso 1 1 calc R . .
H22D H 0.8558 0.2534 0.1900 0.056 Uiso 1 1 calc R . .
C23' C 0.7556(4) 0.3723(7) 0.1920(2) 0.0748(19) Uani 1 1 d D . .


_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
C24' C23' 1.270(9) . ?
C21A C20 1.268(11) . ?
C21B C20 1.060(14) . ?
C24" C23' 1.055(19) . ?
O1 C1 1.318(5) . ?
O2 C1 1.201(5) . ?
O3 C9 1.287(5) . ?
O4 C9 1.223(5) . ?
O5 C15 1.216(5) . ?
O6 C15 1.318(5) . ?
N1 C19 1.486(6) . ?
N1 C22 1.499(6) . ?
C1 C2 1.510(6) . ?
C2 C3 1.523(6) . ?
C3 C4 1.403(6) . ?
C3 C16 1.405(6) . ?
C4 C7 1.407(6) . ?
C4 C5 1.515(6) . ?
C5 C6 1.534(7) . ?
C7 C10 1.396(6) . ?
C7 C8 1.527(6) . ?
C8 C9 1.502(7) . ?
C9 O4 1.223(5) 1 ?
C10 C13 1.409(6) . ?
C10 C11 1.521(6) . ?
C11 C12 1.518(6) . ?
C13 C16 1.398(6) . ?
C13 C14 1.511(6) . ?
C14 C15 1.493(7) . ?
C16 C17 1.518(6) . ?
C17 C18 1.528(7) . ?
C19 C20 1.479(8) . ?
C22 C23 1.489(7) . ?
C23 C24 1.272(8) . ?
O1' C1' 1.294(5) . ?
O2' C1' 1.223(5) . ?
O3' C9' 1.203(5) . ?
O4' C9' 1.330(5) . ?
O5' C15' 1.310(5) . ?
O6' C15' 1.229(6) . ?
N1' C19' 1.484(6) . ?
N1' C22' 1.494(6) . ?
C1' C2' 1.523(7) . ?
C2' C3' 1.516(6) . ?
C3' C16' 1.400(6) . ?
C3' C4' 1.404(6) . ?
C4' C7' 1.398(6) . ?
C4' C5' 1.523(6) . ?
C5' C6' 1.538(7) . ?
C7' C10' 1.410(6) . ?
C7' C8' 1.523(6) . ?
C8' C9' 1.503(6) . ?
C10' C13' 1.400(6) . ?
C10' C11' 1.508(6) . ?
C11' C12' 1.525(7) . ?
C13' C16' 1.405(6) . ?
C13' C14' 1.512(6) . ?
C14' C15' 1.504(7) . ?
C16' C17' 1.519(6) . ?
C17' C18' 1.548(7) . ?
C19' C20' 1.489(7) . ?
C20' C21' 1.270(7) . ?
C22' C23' 1.524(8) . ?

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
C19 N1 C22 113.8(4) . . ?
O2 C1 O1 123.8(4) . . ?
O2 C1 C2 123.6(4) . . ?
O1 C1 C2 112.7(4) . . ?
C1 C2 C3 114.4(4) . . ?
C4 C3 C16 120.9(4) . . ?
C4 C3 C2 119.0(4) . . ?
C16 C3 C2 120.1(4) . . ?
C3 C4 C7 118.9(4) . . ?
C3 C4 C5 121.3(4) . . ?
C7 C4 C5 119.9(4) . . ?
C4 C5 C6 112.4(4) . . ?
C10 C7 C4 121.2(4) . . ?
C10 C7 C8 119.6(4) . . ?
C4 C7 C8 119.2(4) . . ?
C9 C8 C7 117.5(4) . . ?
O4 C9 O3 122.7(4) 1 . ?
O4 C9 O3 122.7(4) . . ?
O4 C9 C8 122.8(4) 1 . ?
O4 C9 C8 122.8(4) . . ?
O3 C9 C8 114.4(4) . . ?
C7 C10 C13 118.7(4) . . ?
C7 C10 C11 120.7(4) . . ?
C13 C10 C11 120.5(4) . . ?
C12 C11 C10 114.4(4) . . ?
C16 C13 C10 121.2(4) . . ?
C16 C13 C14 118.5(4) . . ?
C10 C13 C14 120.4(4) . . ?
C15 C14 C13 114.3(4) . . ?
O5 C15 O6 118.5(5) . . ?
O5 C15 C14 123.2(4) . . ?
O6 C15 C14 118.3(4) . . ?
C13 C16 C3 119.0(4) . . ?
C13 C16 C17 120.0(4) . . ?
C3 C16 C17 121.0(4) . . ?
C16 C17 C18 113.0(4) . . ?
C20 C19 N1 111.3(4) . . ?
C21B C20 C21A 69.0(10) . . ?
C21B C20 C19 138.2(11) . . ?
C21A C20 C19 137.6(9) . . ?
C23 C22 N1 111.1(4) . . ?
C24 C23 C22 125.6(6) . . ?
C19' N1' C22' 113.5(3) . . ?
O2' C1' O1' 123.6(4) . . ?
O2' C1' C2' 123.3(4) . . ?
O1' C1' C2' 113.1(4) . . ?
C3' C2' C1' 116.9(4) . . ?
C16' C3' C4' 120.2(4) . . ?
C16' C3' C2' 119.9(4) . . ?
C4' C3' C2' 119.8(4) . . ?
C7' C4' C3' 119.5(4) . . ?
C7' C4' C5' 120.4(4) . . ?
C3' C4' C5' 120.0(4) . . ?
C4' C5' C6' 115.8(4) . . ?
C4' C7' C10' 120.5(4) . . ?
C4' C7' C8' 119.6(4) . . ?
C10' C7' C8' 119.9(4) . . ?
C9' C8' C7' 113.6(4) . . ?
O3' C9' O4' 122.7(4) . . ?
O3' C9' C8' 124.9(4) . . ?
O4' C9' C8' 112.4(4) . . ?
C13' C10' C7' 119.4(4) . . ?
C13' C10' C11' 121.1(4) . . ?
C7' C10' C11' 119.5(4) . . ?
C10' C11' C12' 114.2(4) . . ?
C10' C13' C16' 120.2(4) . . ?
C10' C13' C14' 118.7(4) . . ?
C16' C13' C14' 121.1(4) . . ?
C15' C14' C13' 113.1(4) . . ?
O6' C15' O5' 118.6(5) . . ?
O6' C15' C14' 122.6(4) . . ?
O5' C15' C14' 118.8(5) . . ?
C3' C16' C13' 119.9(4) . . ?
C3' C16' C17' 119.8(4) . . ?
C13' C16' C17' 120.3(4) . . ?
C16' C17' C18' 114.6(4) . . ?
N1' C19' C20' 112.6(4) . . ?
C21' C20' C19' 126.2(6) . . ?
N1' C22' C23' 109.1(4) . . ?
C24" C23' C24' 78.3(12) . . ?
C24" C23' C22' 135.4(13) . . ?
C24' C23' C22' 128.6(7) . . ?

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' H1'2 O6 0.90 2.52 3.072(5) 120.1 3_565
N1' H1'2 O5 0.90 1.91 2.805(5) 171.0 3_565
O4' H4' O1' 0.82 1.79 2.594(4) 167.4 3_465
N1 H1B O5' 0.90 2.46 3.033(5) 121.5 3_455
N1 H1B O6' 0.90 1.98 2.871(5) 172.5 3_455
N1 H1A O4 0.90 1.81 2.710(5) 174.2 1
O6 H6 O3 0.82 1.68 2.499(4) 173.1 1_565
O1 H1 O3 0.82 1.80 2.621(4) 175.1 3

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        19.47
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.035
# start Validation Reply Form
_vrf_THETM01_tapas               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The crystal was poorly diffracting at higher Bragg angles 
and the problem could not be resolved even after low temperature 
fresh data collection on several crystals. 
;
_vrf_PLAT089_tapas               
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       3.75       
RESPONSE: Z value for the crystal is 8 and it is for this high value of 
Z consequently larger number of parameters and poor diffraction, the data 
parameter ratio is low.
;
_database_code_depnum_ccdc_archive 'CCDC 929284'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_TA0885

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_absolute_configuration R
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 O6, C8 H20 N'
_chemical_formula_sum            'C23 H37 N O6'
_chemical_formula_weight         423.54

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

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.405(11)
_cell_length_b                   16.69(2)
_cell_length_c                   9.156(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.32(8)
_cell_angle_gamma                90.00
_cell_volume                     1141(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.49
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9434
_exptl_absorpt_correction_T_max  0.9581
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 CCD AREA DETECTOR'
_diffrn_measurement_method       'PHI-OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10904
_diffrn_reflns_av_R_equivalents  0.1200
_diffrn_reflns_av_sigmaI/netI    0.0862
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         24.99
_reflns_number_total             4018
_reflns_number_gt                3686
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER APEX II'
_computing_cell_refinement       'BRUKER APEX II'
_computing_data_reduction        'BRUKER APEX II'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'MERCURY 2.3, PLATON'
_computing_publication_material  'MERCURY 2.3, PLATON'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.Acid componet is achiral and amine 
component is meso. so there is no absolute chirality inh the molecule and hance Flac parameter
has no meaning.so it was removed fron the cif.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1140P)²+0.0001P] where P=(Fo²+2Fc²)/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_number_reflns         4018
_refine_ls_number_parameters     286
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1643
_refine_ls_wR_factor_gt          0.1606
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0268(3) 0.73534(13) 0.7991(2) 0.0287(5) Uani 1 1 d . . .
O2 O 0.7303(3) 0.74651(13) 0.6822(2) 0.0280(5) Uani 1 1 d . . .
O3 O 0.7447(3) 0.64210(12) -0.1274(2) 0.0273(5) Uani 1 1 d . . .
O4 O 0.7690(3) 0.61875(12) 0.1189(2) 0.0322(5) Uani 1 1 d . . .
O5 O 0.0821(3) 0.96434(13) 0.0227(3) 0.0406(6) Uani 1 1 d . . .
O6 O 0.3233(3) 0.97780(13) -0.0124(3) 0.0285(5) Uani 1 1 d . . .
N1 N 0.1150(3) 0.57707(14) 0.9040(3) 0.0248(5) Uani 1 1 d . . .
H1A H 0.0324 0.5541 0.9274 0.030 Uiso 1 1 calc R . .
H1B H 0.0821 0.6285 0.8779 0.030 Uiso 1 1 calc R . .
C1 C 0.8860(4) 0.76952(17) 0.7057(3) 0.0210(6) Uani 1 1 d . . .
C2 C 0.8873(4) 0.84306(17) 0.6113(3) 0.0250(6) Uani 1 1 d . . .
H2A H 1.0094 0.8547 0.6334 0.030 Uiso 1 1 calc R . .
H2B H 0.8434 0.8884 0.6487 0.030 Uiso 1 1 calc R . .
C3 C 0.7723(4) 0.83250(15) 0.4276(3) 0.0216(6) Uani 1 1 d . . .
C4 C 0.8485(3) 0.79564(15) 0.3368(3) 0.0197(5) Uani 1 1 d . . .
C5 C 1.0391(4) 0.76424(19) 0.4213(4) 0.0297(7) Uani 1 1 d . . .
H5A H 1.0834 0.7667 0.5383 0.045 Uiso 1 1 calc R . .
H5B H 1.1134 0.7965 0.3904 0.045 Uiso 1 1 calc R . .
H5C H 1.0410 0.7097 0.3887 0.045 Uiso 1 1 calc R . .
C6 C 0.7456(4) 0.78662(15) 0.1670(3) 0.0209(6) Uani 1 1 d . . .
C7 C 0.8263(4) 0.75185(17) 0.0646(4) 0.0235(6) Uani 1 1 d . . .
H7A H 0.9557 0.7559 0.1255 0.028 Uiso 1 1 calc R . .
H7B H 0.7879 0.7835 -0.0347 0.028 Uiso 1 1 calc R . .
C8 C 0.7763(4) 0.66553(17) 0.0173(3) 0.0223(6) Uani 1 1 d . . .
C9 C 0.5640(4) 0.80905(16) 0.0880(3) 0.0213(6) Uani 1 1 d . . .
C10 C 0.4526(4) 0.79712(18) -0.0950(3) 0.0273(6) Uani 1 1 d . . .
H10A H 0.3746 0.8423 -0.1409 0.041 Uiso 1 1 calc R . .
H10B H 0.3823 0.7493 -0.1147 0.041 Uiso 1 1 calc R . .
H10C H 0.5301 0.7922 -0.1455 0.041 Uiso 1 1 calc R . .
C11 C 0.4869(4) 0.84109(15) 0.1804(3) 0.0213(6) Uani 1 1 d . . .
C12 C 0.2878(4) 0.85636(17) 0.1019(3) 0.0234(6) Uani 1 1 d . . .
H12A H 0.2466 0.8442 0.1826 0.028 Uiso 1 1 calc R . .
H12B H 0.2302 0.8186 0.0122 0.028 Uiso 1 1 calc R . .
C13 C 0.2226(4) 0.93945(18) 0.0356(3) 0.0238(6) Uani 1 1 d . . .
C14 C 0.5923(4) 0.85560(17) 0.3491(3) 0.0227(6) Uani 1 1 d . . .
C15 C 0.5090(4) 0.8949(2) 0.4445(4) 0.0351(7) Uani 1 1 d . . .
H15A H 0.5940 0.9307 0.5244 0.053 Uiso 1 1 calc R . .
H15B H 0.4746 0.8547 0.4995 0.053 Uiso 1 1 calc R . .
H15C H 0.4052 0.9246 0.3709 0.053 Uiso 1 1 calc R . .
C16 C 0.3493(4) 0.49134(19) 1.1146(4) 0.0329(7) Uani 1 1 d . . .
H16A H 0.3755 0.4646 1.0352 0.049 Uiso 1 1 calc R . .
H16B H 0.2548 0.4635 1.1245 0.049 Uiso 1 1 calc R . .
H16C H 0.4545 0.4919 1.2191 0.049 Uiso 1 1 calc R . .
C17 C 0.2912(4) 0.57653(18) 1.0590(4) 0.0264(6) Uani 1 1 d . . .
H17 H 0.3818 0.6017 1.0348 0.032 Uiso 1 1 calc R . .
C18 C 0.2677(4) 0.6278(2) 1.1841(4) 0.0373(8) Uani 1 1 d . . .
H18A H 0.1836 0.6019 1.2142 0.045 Uiso 1 1 calc R . .
H18B H 0.2177 0.6792 1.1350 0.045 Uiso 1 1 calc R . .
C19 C 0.4464(5) 0.6415(2) 1.3405(5) 0.0518(10) Uani 1 1 d . . .
H19A H 0.5361 0.6587 1.3099 0.078 Uiso 1 1 calc R . .
H19B H 0.4839 0.5925 1.4017 0.078 Uiso 1 1 calc R . .
H19C H 0.4305 0.6820 1.4071 0.078 Uiso 1 1 calc R . .
C20 C 0.2457(4) 0.5706(3) 0.7129(4) 0.0400(8) Uani 1 1 d . . .
H20A H 0.3624 0.5553 0.7962 0.060 Uiso 1 1 calc R . .
H20B H 0.2364 0.6280 0.7082 0.060 Uiso 1 1 calc R . .
H20C H 0.2279 0.5504 0.6084 0.060 Uiso 1 1 calc R . .
C21 C 0.1060(4) 0.53649(17) 0.7536(4) 0.0275(6) Uani 1 1 d . . .
H21 H 0.1278 0.4790 0.7754 0.033 Uiso 1 1 calc R . .
C22 C -0.0853(4) 0.5490(2) 0.6165(4) 0.0394(8) Uani 1 1 d . . .
H22A H -0.1690 0.5364 0.6590 0.047 Uiso 1 1 calc R . .
H22B H -0.1009 0.6051 0.5851 0.047 Uiso 1 1 calc R . .
C23 C -0.1308(6) 0.4984(3) 0.4646(6) 0.0646(12) Uani 1 1 d . . .
H23A H -0.1174 0.4427 0.4941 0.097 Uiso 1 1 calc R . .
H23B H -0.0516 0.5119 0.4191 0.097 Uiso 1 1 calc R . .
H23C H -0.2523 0.5086 0.3845 0.097 Uiso 1 1 calc R . .
H2 H 0.757(6) 0.694(4) 0.761(5) 0.068(14) Uiso 1 1 d . . .
H6 H 0.278(7) 1.025(4) -0.058(6) 0.065(14) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.236(4) . ?
O2 C1 1.284(4) . ?
O2 H2 1.09(6) . ?
O3 C8 1.287(4) . ?
O4 C8 1.237(4) . ?
O5 C13 1.205(4) . ?
O6 C13 1.289(4) . ?
O6 H6 0.89(6) . ?
N1 C21 1.505(4) . ?
N1 C17 1.509(4) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
C1 C2 1.504(4) . ?
C2 C3 1.517(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C14 1.398(4) . ?
C3 C4 1.404(4) . ?
C4 C6 1.398(4) . ?
C4 C5 1.517(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C9 1.407(4) . ?
C6 C7 1.503(4) . ?
C7 C8 1.508(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C11 1.388(4) . ?
C9 C10 1.511(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C14 1.404(4) . ?
C11 C12 1.510(4) . ?
C12 C13 1.512(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 C15 1.499(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.514(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.513(5) . ?
C17 H17 0.9800 . ?
C18 C19 1.544(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.498(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.534(5) . ?
C21 H21 0.9800 . ?
C22 C23 1.518(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C1 O2 H2 104(3) . . ?
C13 O6 H6 113(3) . . ?
C21 N1 C17 118.2(2) . . ?
C21 N1 H1A 107.8 . . ?
C17 N1 H1A 107.8 . . ?
C21 N1 H1B 107.8 . . ?
C17 N1 H1B 107.8 . . ?
H1A N1 H1B 107.1 . . ?
O1 C1 O2 123.8(3) . . ?
O1 C1 C2 121.2(3) . . ?
O2 C1 C2 115.0(2) . . ?
C1 C2 C3 111.9(2) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C14 C3 C4 119.8(3) . . ?
C14 C3 C2 121.8(3) . . ?
C4 C3 C2 118.4(3) . . ?
C6 C4 C3 119.2(3) . . ?
C6 C4 C5 120.0(2) . . ?
C3 C4 C5 120.8(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 C9 121.0(3) . . ?
C4 C6 C7 120.6(3) . . ?
C9 C6 C7 118.4(3) . . ?
C6 C7 C8 113.7(2) . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
O4 C8 O3 121.6(3) . . ?
O4 C8 C7 119.4(3) . . ?
O3 C8 C7 119.0(2) . . ?
C11 C9 C6 119.3(3) . . ?
C11 C9 C10 120.1(3) . . ?
C6 C9 C10 120.6(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 C14 120.1(3) . . ?
C9 C11 C12 120.1(2) . . ?
C14 C11 C12 119.8(3) . . ?
C11 C12 C13 117.7(2) . . ?
C11 C12 H12A 107.9 . . ?
C13 C12 H12A 107.9 . . ?
C11 C12 H12B 107.9 . . ?
C13 C12 H12B 107.9 . . ?
H12A C12 H12B 107.2 . . ?
O5 C13 O6 124.2(3) . . ?
O5 C13 C12 120.9(3) . . ?
O6 C13 C12 114.8(2) . . ?
C3 C14 C11 120.4(3) . . ?
C3 C14 C15 120.3(3) . . ?
C11 C14 C15 119.3(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 C18 107.2(2) . . ?
N1 C17 C16 110.3(2) . . ?
C18 C17 C16 114.3(3) . . ?
N1 C17 H17 108.3 . . ?
C18 C17 H17 108.3 . . ?
C16 C17 H17 108.3 . . ?
C17 C18 C19 112.1(3) . . ?
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 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C20 C21 N1 109.9(3) . . ?
C20 C21 C22 113.1(3) . . ?
N1 C21 C22 106.3(2) . . ?
C20 C21 H21 109.1 . . ?
N1 C21 H21 109.1 . . ?
C22 C21 H21 109.1 . . ?
C23 C22 C21 113.7(3) . . ?
C23 C22 H22A 108.8 . . ?
C21 C22 H22A 108.8 . . ?
C23 C22 H22B 108.8 . . ?
C21 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
O6 H6 O3 0.89(6) 2.65(6) 3.187(4) 120(4) 2_655
O6 H6 O4 0.89(6) 1.65(6) 2.528(4) 169(5) 2_655
O2 H2 O3 1.09(6) 1.39(5) 2.429(4) 159(5) 1_556
N1 H1B O1 0.90 1.90 2.792(4) 171.2 1_455
N1 H1A O5 0.90 1.94 2.784(4) 154.5 2_546

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.863
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.064
# start Validation Reply Form
_vrf_DIFMX01_TA0885              
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00
RESPONSE: We were not able to find out suitable
model for the smeared electron densities (0.86e/angstrom cube 
0.52 angstrom away from H20C) present in the e-map.
;
_vrf_PLAT097_TA0885              
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.86 eA-3  
RESPONSE: We were not able to find out suitable
model for the smeared electron densities (0.86e/angstrom cube 
0.52 angstrom away from H20C) present in the e-map.
;
_database_code_depnum_ccdc_archive 'CCDC 929285'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_iacs_ta

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 O6, C6 H16 N'
_chemical_formula_sum            'C21 H33 N O6'
_chemical_formula_weight         379.36

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

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_hall  '-P 2ybc'

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

_cell_length_a                   14.566(10)
_cell_length_b                   9.991(7)
_cell_length_c                   17.129(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.740(13)
_cell_angle_gamma                90.00
_cell_volume                     2299(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BOLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.096
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9753
_exptl_absorpt_correction_T_max  0.9839
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 CCD AREA DETECTOR'
_diffrn_measurement_method       'PHI-OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10415
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0601
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4035
_reflns_number_gt                2223
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER APEX II'
_computing_cell_refinement       'BRUKER APEX II'
_computing_data_reduction        'BRUKER APEX II'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'MERCURY 2.3, PLATON'
_computing_publication_material  'MERCURY 2.3, PLATON'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1513P)²+0.3672P] where P=(Fo²+2Fc²)/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         4035
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1429
_refine_ls_R_factor_gt           0.0866
_refine_ls_wR_factor_ref         0.2754
_refine_ls_wR_factor_gt          0.2308
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C17A C -0.0189(11) 0.8090(16) 0.3502(10) 0.118(4) Uiso 0.43 1 d P A 1
C20A C 0.1274(10) 0.8251(14) 0.1761(8) 0.122(4) Uiso 0.57 1 d P A 1
C21A C 0.1073(10) 0.8221(15) 0.0838(9) 0.137(4) Uiso 0.58 1 d P A 1
N1A N 0.1173(4) 0.9450(5) 0.3024(3) 0.0600(14) Uiso 0.60 1 d P A 1
C17B C 0.0147(7) 0.8994(11) 0.3853(7) 0.102(3) Uiso 0.57 1 d P A 2
C20B C 0.1229(19) 0.897(3) 0.1315(19) 0.191(9) Uiso 0.43 1 d P A 2
C21B C 0.1810(19) 0.772(3) 0.1524(16) 0.182(8) Uiso 0.42 1 d P A 2
N1B N 0.0638(6) 0.8436(8) 0.2501(5) 0.066(2) Uiso 0.40 1 d P A 2
O1 O 0.4105(2) -0.0365(4) 0.1440(2) 0.1006(12) Uani 1 1 d . . .
H1 H 0.3658 -0.0497 0.0977 0.151 Uiso 1 1 calc R . .
O2 O 0.3056(3) 0.1137(4) 0.1515(2) 0.1084(13) Uani 1 1 d . . .
O3 O 0.14439(18) 0.4150(2) 0.4113(2) 0.0748(9) Uani 1 1 d . . .
H3 H 0.1914 0.4637 0.4381 0.112 Uiso 1 1 calc R . .
O4 O 0.11851(19) 0.2077(3) 0.3674(2) 0.0800(10) Uani 1 1 d . . .
O5 O 0.2177(2) -0.2860(3) 0.3781(2) 0.1017(12) Uani 1 1 d . . .
O6 O 0.2854(2) -0.4210(2) 0.48676(18) 0.0719(8) Uani 1 1 d . . .
C1 C 0.3819(3) 0.0510(5) 0.1852(3) 0.0659(11) Uani 1 1 d . . .
C2 C 0.4541(3) 0.0694(5) 0.2765(3) 0.0710(12) Uani 1 1 d . . .
H2A H 0.4828 0.1583 0.2829 0.085 Uiso 1 1 calc R . .
H2B H 0.5079 0.0053 0.2888 0.085 Uiso 1 1 calc R . .
C3 C 0.4063(2) 0.0517(4) 0.3414(2) 0.0501(9) Uani 1 1 d . . .
C4 C 0.3647(2) 0.1613(3) 0.3663(2) 0.0519(9) Uani 1 1 d . . .
C5 C 0.3581(4) 0.2976(4) 0.3229(3) 0.0824(14) Uani 1 1 d . . .
H5A H 0.3008 0.3453 0.3227 0.124 Uiso 1 1 calc R . .
H5B H 0.3523 0.2840 0.2657 0.124 Uiso 1 1 calc R . .
H5C H 0.4171 0.3486 0.3531 0.124 Uiso 1 1 calc R . .
C6 C 0.3275(2) 0.1461(3) 0.4296(2) 0.0483(9) Uani 1 1 d . . .
C7 C 0.2869(3) 0.2685(4) 0.4590(3) 0.0651(11) Uani 1 1 d . . .
H7A H 0.2976 0.2570 0.5181 0.078 Uiso 1 1 calc R . .
H7B H 0.3242 0.3467 0.4549 0.078 Uiso 1 1 calc R . .
C8 C 0.1770(3) 0.2938(4) 0.4086(2) 0.0572(10) Uani 1 1 d . . .
C9 C 0.3291(2) 0.0207(4) 0.4674(2) 0.0483(9) Uani 1 1 d . . .
C10 C 0.2845(3) 0.0053(5) 0.5337(3) 0.0810(14) Uani 1 1 d . . .
H10A H 0.2680 -0.0870 0.5371 0.121 Uiso 1 1 calc R . .
H10B H 0.2254 0.0589 0.5181 0.121 Uiso 1 1 calc R . .
H10C H 0.3319 0.0342 0.5876 0.121 Uiso 1 1 calc R . .
C11 C 0.3708(2) -0.0897(3) 0.4422(2) 0.0482(9) Uani 1 1 d . . .
C12 C 0.3765(3) -0.2243(4) 0.4854(3) 0.0625(11) Uani 1 1 d . . .
H12A H 0.3866 -0.2084 0.5440 0.075 Uiso 1 1 calc R . .
H12B H 0.4343 -0.2721 0.4852 0.075 Uiso 1 1 calc R . .
C13 C 0.2846(3) -0.3141(4) 0.4452(3) 0.0586(10) Uani 1 1 d . . .
C14 C 0.4082(2) -0.0757(4) 0.3785(2) 0.0508(9) Uani 1 1 d . . .
C15 C 0.4475(3) -0.1961(4) 0.3476(3) 0.0824(14) Uani 1 1 d . . .
H15A H 0.4524 -0.1750 0.2946 0.124 Uiso 1 1 calc R . .
H15B H 0.4029 -0.2702 0.3399 0.124 Uiso 1 1 calc R . .
H15C H 0.5121 -0.2194 0.3885 0.124 Uiso 1 1 calc R . .
C16 C 0.0160(3) 0.9148(5) 0.2996(3) 0.0867(14) Uani 1 1 d . . .
C19 C 0.1159(4) 0.9559(5) 0.2128(4) 0.0959(16) Uani 1 1 d . . .
C18 C -0.0883(6) 0.8680(10) 0.3872(6) 0.180(4) Uani 1 1 d . . .


_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
C17A C18 1.506(16) . ?
C17A C16 1.571(16) . ?
C20A C19 1.488(14) . ?
C20A C21A 1.492(19) . ?
N1A C16 1.489(7) . ?
N1A C19 1.530(8) . ?
C17B C16 1.482(11) . ?
C17B C18 1.546(12) . ?
C20B C21B 1.47(3) . ?
C20B C19 1.55(3) . ?
N1B C16 1.472(9) . ?
N1B C19 1.617(9) . ?
O1 C1 1.289(5) . ?
O2 C1 1.209(5) . ?
O3 C8 1.308(4) . ?
O4 C8 1.223(4) . ?
O5 C13 1.218(4) . ?
O6 C13 1.281(4) . ?
C1 C2 1.522(6) . ?
C2 C3 1.532(5) . ?
C3 C4 1.395(5) . ?
C3 C14 1.418(5) . ?
C4 C6 1.396(5) . ?
C4 C5 1.537(5) . ?
C6 C9 1.405(5) . ?
C6 C7 1.526(5) . ?
C7 C8 1.518(5) . ?
C9 C11 1.405(5) . ?
C9 C10 1.518(5) . ?
C11 C14 1.401(5) . ?
C11 C12 1.522(5) . ?
C12 C13 1.536(5) . ?
C14 C15 1.513(5) . ?

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


C18 C17A C16 112.4(11) . . ?
C19 C20A C21A 117.2(12) . . ?
C16 N1A C19 110.7(4) . . ?
C16 C17B C18 115.2(8) . . ?
C21B C20B C19 109(2) . . ?
C16 N1B C19 107.0(6) . . ?
O2 C1 O1 121.5(4) . . ?
O2 C1 C2 124.7(4) . . ?
O1 C1 C2 113.7(4) . . ?
C1 C2 C3 113.8(3) . . ?
C4 C3 C14 120.1(3) . . ?
C4 C3 C2 120.3(3) . . ?
C14 C3 C2 119.6(3) . . ?
C3 C4 C6 119.8(3) . . ?
C3 C4 C5 120.0(4) . . ?
C6 C4 C5 120.1(4) . . ?
C4 C6 C9 120.8(3) . . ?
C4 C6 C7 119.0(3) . . ?
C9 C6 C7 120.2(3) . . ?
C8 C7 C6 113.8(3) . . ?
O4 C8 O3 119.4(3) . . ?
O4 C8 C7 123.8(3) . . ?
O3 C8 C7 116.8(3) . . ?
C11 C9 C6 119.4(3) . . ?
C11 C9 C10 120.7(3) . . ?
C6 C9 C10 119.9(3) . . ?
C14 C11 C9 120.3(3) . . ?
C14 C11 C12 120.2(3) . . ?
C9 C11 C12 119.5(3) . . ?
C11 C12 C13 115.1(3) . . ?
O5 C13 O6 123.3(4) . . ?
O5 C13 C12 122.0(4) . . ?
O6 C13 C12 114.8(3) . . ?
C11 C14 C3 119.5(3) . . ?
C11 C14 C15 120.4(4) . . ?
C3 C14 C15 120.0(4) . . ?
N1B C16 C17B 135.3(6) . . ?
N1B C16 N1A 55.4(4) . . ?
C17B C16 N1A 112.4(5) . . ?
N1B C16 C17A 108.6(7) . . ?
N1A C16 C17A 130.3(7) . . ?
C20A C19 N1A 113.7(7) . . ?
N1A C19 C20B 153.4(12) . . ?
C20A C19 N1B 72.9(7) . . ?
N1A C19 N1B 51.8(4) . . ?
C20B C19 N1B 107.2(11) . . ?


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
O1 H1 O6 0.82 1.83 2.639(5) 168.8 4
O3 H3 O6 0.82 1.74 2.553(4) 174.2 1_565

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.065
_database_code_depnum_ccdc_archive 'CCDC 929286'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ta0880-mono

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 O6, C8 H20 N'
_chemical_formula_sum            'C23 H37 N O6'
_chemical_formula_weight         423.54

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.494(5)
_cell_length_b                   8.794(5)
_cell_length_c                   19.179(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.665(5)
_cell_angle_gamma                90
_cell_volume                     2271.9(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9655
_exptl_absorpt_correction_T_max  0.9723
_exptl_absorpt_process_details   SADABS
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 CCD AREA DETECTOR'
_diffrn_measurement_method       'PHI-OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24321
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4245
_reflns_number_gt                3380
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER APEX II'
_computing_cell_refinement       'BRUKER APEX II'
_computing_data_reduction        'BRUKER APEX II'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'MERCURY 2.3, PLATON'
_computing_publication_material  'MERCURY 2.3, PLATON'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0711P)²+0.9129P] where P=(Fo²+2Fc²)/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         4245
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1483
_refine_ls_wR_factor_gt          0.1366
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
O1 O 0.26799(10) 0.88649(14) 1.07917(8) 0.0377(3) Uani 1 1 d . . .
O2 O 0.20942(12) 0.97591(17) 1.16185(8) 0.0501(4) Uani 1 1 d . . .
O3 O 0.38292(10) 0.11691(15) 1.09165(9) 0.0455(4) Uani 1 1 d . . .
H3 H 0.3421 0.0528 1.0922 0.068 Uiso 1 1 calc R . .
O4 O 0.38394(11) 0.35313(16) 1.05582(10) 0.0487(4) Uani 1 1 d . . .
O5 O 0.10072(18) 0.4919(2) 0.74098(12) 0.0775(6) Uani 1 1 d . . .
H5 H 0.1369 0.5216 0.7195 0.116 Uiso 1 1 calc R . .
O6 O 0.10901(17) 0.7313(2) 0.77365(12) 0.0742(6) Uani 1 1 d . . .
N1 N 0.37879(12) 0.67615(18) 0.03262(9) 0.0333(4) Uani 1 1 d . . .
H1A H 0.3383 0.7429 0.0427 0.040 Uiso 1 1 calc R . .
H1B H 0.3682 0.5841 0.0488 0.040 Uiso 1 1 calc R . .
C1 C 0.20579(14) 0.8854(2) 1.11174(10) 0.0303(4) Uani 1 1 d . . .
C2 C 0.12060(15) 0.7727(2) 1.08558(12) 0.0377(5) Uani 1 1 d . . .
H2A H 0.1156 0.7248 1.1296 0.045 Uiso 1 1 calc R . .
H2B H 0.0597 0.8294 1.0612 0.045 Uiso 1 1 calc R . .
C3 C 0.12580(13) 0.6484(2) 1.03258(10) 0.0305(4) Uani 1 1 d . . .
C4 C 0.07977(13) 0.6668(2) 0.95480(11) 0.0310(4) Uani 1 1 d . . .
C5 C 0.03301(18) 0.8182(2) 0.92325(13) 0.0484(5) Uani 1 1 d . . .
H5A H 0.0343 0.8317 0.8740 0.073 Uiso 1 1 calc R . .
H5B H 0.0695 0.8988 0.9554 0.073 Uiso 1 1 calc R . .
H5C H -0.0345 0.8200 0.9204 0.073 Uiso 1 1 calc R . .
C6 C 0.07772(13) 0.5459(2) 0.90674(10) 0.0305(4) Uani 1 1 d . . .
C7 C 0.01912(14) 0.5604(3) 0.82211(11) 0.0392(5) Uani 1 1 d . . .
H7A H -0.0133 0.4642 0.8034 0.047 Uiso 1 1 calc R . .
H7B H -0.0323 0.6365 0.8139 0.047 Uiso 1 1 calc R . .
C8 C 0.08180(15) 0.6034(2) 0.77755(11) 0.0385(5) Uani 1 1 d . . .
C9 C 0.12643(13) 0.4087(2) 0.93583(11) 0.0312(4) Uani 1 1 d . . .
C10 C 0.12769(18) 0.2789(2) 0.88464(13) 0.0465(5) Uani 1 1 d . . .
H10A H 0.1950 0.2485 0.8949 0.070 Uiso 1 1 calc R . .
H10B H 0.0977 0.3112 0.8333 0.070 Uiso 1 1 calc R . .
H10C H 0.0911 0.1946 0.8932 0.070 Uiso 1 1 calc R . .
C11 C 0.17513(13) 0.3935(2) 1.01371(11) 0.0314(4) Uani 1 1 d . . .
C12 C 0.22678(14) 0.2460(2) 1.04584(12) 0.0378(5) Uani 1 1 d . . .
H12A H 0.2145 0.2231 1.0911 0.045 Uiso 1 1 calc R . .
H12B H 0.1972 0.1653 1.0101 0.045 Uiso 1 1 calc R . .
C13 C 0.33707(14) 0.2449(2) 1.06445(11) 0.0335(4) Uani 1 1 d . . .
C14 C 0.17438(13) 0.5121(2) 1.06219(10) 0.0322(4) Uani 1 1 d . . .
C15 C 0.22646(18) 0.4921(3) 1.14597(12) 0.0508(6) Uani 1 1 d . . .
H15A H 0.2343 0.5894 1.1701 0.076 Uiso 1 1 calc R . .
H15B H 0.2906 0.4473 1.1563 0.076 Uiso 1 1 calc R . .
H15C H 0.1876 0.4269 1.1646 0.076 Uiso 1 1 calc R . .
C16 C 0.48419(16) 0.7219(3) 0.07491(11) 0.0419(5) Uani 1 1 d . . .
H16A H 0.4884 0.8320 0.0750 0.050 Uiso 1 1 calc R . .
H16B H 0.5250 0.6830 0.0487 0.050 Uiso 1 1 calc R . .
C17 C 0.52619(18) 0.6662(3) 0.15509(13) 0.0522(6) Uani 1 1 d . . .
H17 H 0.5109 0.5577 0.1555 0.063 Uiso 1 1 calc R . .
C18 C 0.6386(2) 0.6855(4) 0.18661(15) 0.0688(8) Uani 1 1 d . . .
H18A H 0.6661 0.6382 0.1535 0.103 Uiso 1 1 calc R . .
H18B H 0.6658 0.6385 0.2351 0.103 Uiso 1 1 calc R . .
H18C H 0.6548 0.7918 0.1911 0.103 Uiso 1 1 calc R . .
C19 C 0.4823(3) 0.7486(5) 0.20403(16) 0.1017(13) Uani 1 1 d . . .
H19A H 0.5016 0.8537 0.2078 0.153 Uiso 1 1 calc R . .
H19B H 0.5060 0.7037 0.2531 0.153 Uiso 1 1 calc R . .
H19C H 0.4113 0.7413 0.1825 0.153 Uiso 1 1 calc R . .
C20 C 0.35241(16) 0.6695(2) -0.05101(11) 0.0394(5) Uani 1 1 d . . .
H20A H 0.2832 0.6402 -0.0745 0.047 Uiso 1 1 calc R . .
H20B H 0.3919 0.5906 -0.0618 0.047 Uiso 1 1 calc R . .
C21 C 0.36790(16) 0.8162(2) -0.08638(11) 0.0425(5) Uani 1 1 d . . .
H21 H 0.4344 0.8550 -0.0572 0.051 Uiso 1 1 calc R . .
C22 C 0.2926(2) 0.9366(3) -0.08765(15) 0.0669(8) Uani 1 1 d . . .
H22A H 0.3069 1.0290 -0.1083 0.100 Uiso 1 1 calc R . .
H22B H 0.2958 0.9550 -0.0374 0.100 Uiso 1 1 calc R . .
H22C H 0.2272 0.9021 -0.1180 0.100 Uiso 1 1 calc R . .
C23 C 0.3622(2) 0.7829(3) -0.16561(13) 0.0617(7) Uani 1 1 d . . .
H23A H 0.2978 0.7432 -0.1947 0.093 Uiso 1 1 calc R . .
H23B H 0.4120 0.7095 -0.1639 0.093 Uiso 1 1 calc R . .
H23C H 0.3733 0.8750 -0.1882 0.093 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.272(2) . ?
O2 C1 1.234(2) . ?
O3 C13 1.314(2) . ?
O3 H3 0.8200 . ?
O4 C13 1.215(2) . ?
O5 C8 1.293(3) . ?
O5 H5 0.8200 . ?
O6 C8 1.203(3) . ?
N1 C16 1.496(3) . ?
N1 C20 1.507(2) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
C1 C2 1.517(3) . ?
C2 C3 1.514(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C14 1.400(3) . ?
C3 C4 1.401(3) . ?
C4 C6 1.400(3) . ?
C4 C5 1.515(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C9 1.405(3) . ?
C6 C7 1.534(3) . ?
C7 C8 1.507(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C11 1.403(3) . ?
C9 C10 1.510(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C14 1.399(3) . ?
C11 C12 1.511(3) . ?
C12 C13 1.504(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 C15 1.512(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.511(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C19 1.500(4) . ?
C17 C18 1.524(4) . ?
C17 H17 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.512(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.515(3) . ?
C21 C23 1.520(3) . ?
C21 H21 0.9800 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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 O3 H3 109.5 . . ?
C8 O5 H5 109.5 . . ?
C16 N1 C20 113.24(15) . . ?
C16 N1 H1A 108.9 . . ?
C20 N1 H1A 108.9 . . ?
C16 N1 H1B 108.9 . . ?
C20 N1 H1B 108.9 . . ?
H1A N1 H1B 107.7 . . ?
O2 C1 O1 122.93(18) . . ?
O2 C1 C2 118.32(16) . . ?
O1 C1 C2 118.69(16) . . ?
C3 C2 C1 117.25(15) . . ?
C3 C2 H2A 108.0 . . ?
C1 C2 H2A 108.0 . . ?
C3 C2 H2B 108.0 . . ?
C1 C2 H2B 108.0 . . ?
H2A C2 H2B 107.2 . . ?
C14 C3 C4 120.11(16) . . ?
C14 C3 C2 119.24(17) . . ?
C4 C3 C2 120.61(17) . . ?
C6 C4 C3 119.93(17) . . ?
C6 C4 C5 120.46(18) . . ?
C3 C4 C5 119.61(17) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 C9 120.36(17) . . ?
C4 C6 C7 120.12(17) . . ?
C9 C6 C7 119.49(17) . . ?
C8 C7 C6 113.99(16) . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.6 . . ?
O6 C8 O5 122.4(2) . . ?
O6 C8 C7 123.4(2) . . ?
O5 C8 C7 114.21(19) . . ?
C11 C9 C6 119.05(16) . . ?
C11 C9 C10 119.90(17) . . ?
C6 C9 C10 121.05(18) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C14 C11 C9 120.82(17) . . ?
C14 C11 C12 119.52(17) . . ?
C9 C11 C12 119.64(17) . . ?
C13 C12 C11 115.19(15) . . ?
C13 C12 H12A 108.5 . . ?
C11 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C11 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
O4 C13 O3 119.92(18) . . ?
O4 C13 C12 124.14(17) . . ?
O3 C13 C12 115.94(16) . . ?
C11 C14 C3 119.62(17) . . ?
C11 C14 C15 119.75(18) . . ?
C3 C14 C15 120.63(18) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C17 114.31(17) . . ?
N1 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
N1 C16 H16B 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C19 C17 C16 112.1(2) . . ?
C19 C17 C18 109.6(2) . . ?
C16 C17 C18 109.74(19) . . ?
C19 C17 H17 108.4 . . ?
C16 C17 H17 108.4 . . ?
C18 C17 H17 108.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 C21 115.04(16) . . ?
N1 C20 H20A 108.5 . . ?
C21 C20 H20A 108.5 . . ?
N1 C20 H20B 108.5 . . ?
C21 C20 H20B 108.5 . . ?
H20A C20 H20B 107.5 . . ?
C20 C21 C22 112.21(18) . . ?
C20 C21 C23 108.78(19) . . ?
C22 C21 C23 110.25(19) . . ?
C20 C21 H21 108.5 . . ?
C22 C21 H21 108.5 . . ?
C23 C21 H21 108.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
O3 H3 O1 0.82 1.78 2.578(2) 164.9 1_545
O5 H5 O2 0.82 1.79 2.575(2) 161.2 4_575
N1 H1A O1 0.90 1.91 2.803(2) 171.2 1_554
N1 H1B O4 0.90 2.04 2.872(3) 152.6 1_554

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 929287'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_tka

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H72 N3,C15 H15 O6, H2 O'
_chemical_formula_sum            'C51 H89 N3 O7'
_chemical_formula_weight         856.25

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   Fdd2
_symmetry_space_group_name_Hall  'F 2 -2d'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+3/4, -y+5/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+5/4, -y+3/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+5/4, -y+5/4, z+1/4'

_cell_length_a                   29.446(14)
_cell_length_b                   39.144(19)
_cell_length_c                   17.410(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     20067(16)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             7552
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9738
_exptl_absorpt_correction_T_max  0.9853
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II'
_diffrn_measurement_method       'Omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43331
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         6.22
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4494
_reflns_number_gt                3779
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Apex II'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury 2.3'
_computing_publication_material  'Mercury 2.3'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0582P)²+3.9766P] where P=(Fo²+2Fc²)/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_number_reflns         4494
_refine_ls_number_parameters     561
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1067
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.147
_refine_ls_shift/su_max          0.018
_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
O1 O 0.22034(8) 0.08508(6) 0.39592(12) 0.0715(6) Uani 1 1 d . . .
O2 O 0.26971(7) 0.08339(7) 0.30128(13) 0.0786(7) Uani 1 1 d . . .
O3 O 0.18625(8) -0.09897(5) 0.53506(16) 0.0818(7) Uani 1 1 d . . .
O4 O 0.25343(8) -0.07748(5) 0.56562(14) 0.0712(6) Uani 1 1 d . . .
O5 O 0.20306(7) 0.09224(6) 0.67878(13) 0.0694(6) Uani 1 1 d . . .
O6 O 0.24276(11) 0.09632(8) 0.78303(16) 0.1085(10) Uani 1 1 d . . .
O7 O 0.04608(10) 0.12127(9) 0.6401(2) 0.0980(9) Uani 1 1 d . . .
N1 N 0.17560(7) 0.10521(5) 0.52867(13) 0.0483(5) Uani 1 1 d . . .
H1A H 0.1892 0.0992 0.5730 0.058 Uiso 1 1 calc R . .
H1B H 0.1927 0.0971 0.4900 0.058 Uiso 1 1 calc R . .
N2 N 0.20780(7) 0.10351(5) 0.19854(13) 0.0489(5) Uani 1 1 d . . .
H2A H 0.2267 0.0968 0.2363 0.059 Uiso 1 1 calc R . .
H2B H 0.2217 0.0990 0.1536 0.059 Uiso 1 1 calc R . .
N3 N 0.39627(8) 0.12999(6) 0.06541(14) 0.0570(6) Uani 1 1 d . . .
H3A H 0.3745 0.1170 0.0440 0.068 Uiso 1 1 calc R . .
H3B H 0.4157 0.1358 0.0277 0.068 Uiso 1 1 calc R . .
C1 C 0.25655(9) 0.07532(7) 0.36684(16) 0.0497(6) Uani 1 1 d . . .
C2 C 0.28776(10) 0.05092(9) 0.41046(18) 0.0645(8) Uani 1 1 d . . .
H2C H 0.2963 0.0325 0.3761 0.077 Uiso 1 1 calc R . .
H2D H 0.3153 0.0631 0.4238 0.077 Uiso 1 1 calc R . .
C3 C 0.26828(8) 0.03535(7) 0.48320(15) 0.0465(6) Uani 1 1 d . . .
C4 C 0.24226(9) 0.00545(7) 0.47893(16) 0.0487(6) Uani 1 1 d . . .
C5 C 0.23350(14) -0.01120(10) 0.4017(2) 0.0827(11) Uani 1 1 d . . .
H5A H 0.2314 -0.0355 0.4082 0.124 Uiso 1 1 calc R . .
H5B H 0.2580 -0.0060 0.3673 0.124 Uiso 1 1 calc R . .
H5C H 0.2055 -0.0027 0.3808 0.124 Uiso 1 1 calc R . .
C6 C 0.22301(8) -0.00820(6) 0.54547(16) 0.0470(6) Uani 1 1 d . . .
C7 C 0.19197(10) -0.03897(7) 0.5396(2) 0.0688(8) Uani 1 1 d . . .
H7A H 0.1769 -0.0380 0.4901 0.083 Uiso 1 1 calc R . .
H7B H 0.1686 -0.0366 0.5786 0.083 Uiso 1 1 calc R . .
C8 C 0.21278(10) -0.07453(6) 0.54801(16) 0.0521(6) Uani 1 1 d . . .
C9 C 0.23039(8) 0.00767(6) 0.61685(15) 0.0448(6) Uani 1 1 d . . .
C10 C 0.20693(12) -0.00665(10) 0.6873(2) 0.0777(9) Uani 1 1 d . . .
H10A H 0.2199 0.0034 0.7326 0.117 Uiso 1 1 calc R . .
H10B H 0.2110 -0.0310 0.6889 0.117 Uiso 1 1 calc R . .
H10C H 0.1751 -0.0014 0.6851 0.117 Uiso 1 1 calc R . .
C11 C 0.25701(8) 0.03685(6) 0.62132(15) 0.0444(6) Uani 1 1 d . . .
C12 C 0.26626(11) 0.05412(8) 0.69724(17) 0.0628(8) Uani 1 1 d . . .
H12A H 0.2972 0.0626 0.6964 0.075 Uiso 1 1 calc R . .
H12B H 0.2646 0.0369 0.7372 0.075 Uiso 1 1 calc R . .
C13 C 0.23544(10) 0.08351(7) 0.71999(15) 0.0508(6) Uani 1 1 d . . .
C14 C 0.27553(8) 0.05111(6) 0.55380(16) 0.0457(6) Uani 1 1 d . . .
C15 C 0.30203(10) 0.08397(8) 0.5601(3) 0.0768(10) Uani 1 1 d . . .
H15A H 0.2863 0.0995 0.5936 0.115 Uiso 1 1 calc R . .
H15B H 0.3050 0.0941 0.5101 0.115 Uiso 1 1 calc R . .
H15C H 0.3317 0.0793 0.5805 0.115 Uiso 1 1 calc R . .
C16 C 0.12980(8) 0.08810(6) 0.52531(16) 0.0482(6) Uani 1 1 d . . .
H16 H 0.1109 0.0976 0.5664 0.058 Uiso 1 1 calc R . .
C17 C 0.10614(12) 0.09435(10) 0.4502(2) 0.0807(10) Uani 1 1 d . . .
H17A H 0.1255 0.0869 0.4083 0.097 Uiso 1 1 calc R . .
H17B H 0.1006 0.1186 0.4440 0.097 Uiso 1 1 calc R . .
C18 C 0.06117(14) 0.07512(11) 0.4469(3) 0.1023(14) Uani 1 1 d . . .
H18A H 0.0405 0.0847 0.4845 0.123 Uiso 1 1 calc R . .
H18B H 0.0477 0.0780 0.3965 0.123 Uiso 1 1 calc R . .
C19 C 0.06722(14) 0.03756(10) 0.4628(3) 0.0969(13) Uani 1 1 d . . .
H19A H 0.0849 0.0273 0.4217 0.116 Uiso 1 1 calc R . .
H19B H 0.0377 0.0265 0.4638 0.116 Uiso 1 1 calc R . .
C20 C 0.09097(12) 0.03171(10) 0.5384(3) 0.0890(11) Uani 1 1 d . . .
H20A H 0.0962 0.0074 0.5455 0.107 Uiso 1 1 calc R . .
H20B H 0.0718 0.0396 0.5800 0.107 Uiso 1 1 calc R . .
C21 C 0.13618(11) 0.05057(7) 0.5408(2) 0.0695(8) Uani 1 1 d . . .
H21A H 0.1500 0.0475 0.5909 0.083 Uiso 1 1 calc R . .
H21B H 0.1565 0.0410 0.5027 0.083 Uiso 1 1 calc R . .
C22 C 0.17502(9) 0.14361(7) 0.52356(16) 0.0517(6) Uani 1 1 d . . .
H22 H 0.1584 0.1501 0.4771 0.062 Uiso 1 1 calc R . .
C23 C 0.15142(12) 0.15971(8) 0.5921(2) 0.0760(10) Uani 1 1 d . . .
H23A H 0.1662 0.1523 0.6390 0.091 Uiso 1 1 calc R . .
H23B H 0.1201 0.1521 0.5938 0.091 Uiso 1 1 calc R . .
C24 C 0.15275(12) 0.19844(8) 0.5871(3) 0.0840(11) Uani 1 1 d . . .
H24A H 0.1343 0.2058 0.5440 0.101 Uiso 1 1 calc R . .
H24B H 0.1396 0.2080 0.6335 0.101 Uiso 1 1 calc R . .
C25 C 0.19992(13) 0.21215(8) 0.5775(2) 0.0770(9) Uani 1 1 d . . .
H25A H 0.1986 0.2367 0.5699 0.092 Uiso 1 1 calc R . .
H25B H 0.2173 0.2077 0.6237 0.092 Uiso 1 1 calc R . .
C26 C 0.22310(13) 0.19588(10) 0.5101(3) 0.0878(12) Uani 1 1 d . . .
H26A H 0.2542 0.2039 0.5073 0.105 Uiso 1 1 calc R . .
H26B H 0.2078 0.2026 0.4632 0.105 Uiso 1 1 calc R . .
C27 C 0.22290(10) 0.15682(9) 0.5165(2) 0.0741(9) Uani 1 1 d . . .
H27A H 0.2371 0.1470 0.4714 0.089 Uiso 1 1 calc R . .
H27B H 0.2403 0.1499 0.5612 0.089 Uiso 1 1 calc R . .
C28 C 0.16574(9) 0.08212(7) 0.20298(17) 0.0533(7) Uani 1 1 d . . .
H28 H 0.1507 0.0870 0.2520 0.064 Uiso 1 1 calc R . .
C29 C 0.13282(12) 0.09034(9) 0.1391(2) 0.0800(10) Uani 1 1 d . . .
H29A H 0.1472 0.0863 0.0898 0.096 Uiso 1 1 calc R . .
H29B H 0.1243 0.1143 0.1417 0.096 Uiso 1 1 calc R . .
C30 C 0.09008(15) 0.06789(12) 0.1465(4) 0.1140(16) Uani 1 1 d . . .
H30A H 0.0745 0.0733 0.1941 0.137 Uiso 1 1 calc R . .
H30B H 0.0696 0.0728 0.1043 0.137 Uiso 1 1 calc R . .
C31 C 0.10242(17) 0.03044(11) 0.1456(3) 0.1025(14) Uani 1 1 d . . .
H31A H 0.0753 0.0169 0.1534 0.123 Uiso 1 1 calc R . .
H31B H 0.1150 0.0245 0.0959 0.123 Uiso 1 1 calc R . .
C32 C 0.13642(15) 0.02225(9) 0.2072(3) 0.0931(12) Uani 1 1 d . . .
H32A H 0.1453 -0.0015 0.2029 0.112 Uiso 1 1 calc R . .
H32B H 0.1224 0.0254 0.2571 0.112 Uiso 1 1 calc R . .
C33 C 0.17839(12) 0.04456(8) 0.2018(2) 0.0746(9) Uani 1 1 d . . .
H33A H 0.1946 0.0394 0.1547 0.089 Uiso 1 1 calc R . .
H33B H 0.1984 0.0396 0.2446 0.089 Uiso 1 1 calc R . .
C34 C 0.20160(8) 0.14135(7) 0.20457(17) 0.0500(6) Uani 1 1 d . . .
H34 H 0.1823 0.1489 0.1620 0.060 Uiso 1 1 calc R . .
C35 C 0.17868(10) 0.15123(7) 0.27944(19) 0.0607(7) Uani 1 1 d . . .
H35A H 0.1966 0.1429 0.3223 0.073 Uiso 1 1 calc R . .
H35B H 0.1490 0.1405 0.2821 0.073 Uiso 1 1 calc R . .
C36 C 0.17342(10) 0.18977(8) 0.2858(2) 0.0701(9) Uani 1 1 d . . .
H36A H 0.1527 0.1977 0.2463 0.084 Uiso 1 1 calc R . .
H36B H 0.1604 0.1954 0.3353 0.084 Uiso 1 1 calc R . .
C37 C 0.21861(12) 0.20792(9) 0.2770(2) 0.0777(10) Uani 1 1 d . . .
H37A H 0.2137 0.2324 0.2766 0.093 Uiso 1 1 calc R . .
H37B H 0.2379 0.2025 0.3206 0.093 Uiso 1 1 calc R . .
C38 C 0.24225(11) 0.19746(8) 0.2038(2) 0.0776(10) Uani 1 1 d . . .
H38A H 0.2721 0.2079 0.2022 0.093 Uiso 1 1 calc R . .
H38B H 0.2251 0.2059 0.1603 0.093 Uiso 1 1 calc R . .
C39 C 0.24733(9) 0.15873(8) 0.19699(19) 0.0617(7) Uani 1 1 d . . .
H39A H 0.2606 0.1531 0.1476 0.074 Uiso 1 1 calc R . .
H39B H 0.2676 0.1505 0.2369 0.074 Uiso 1 1 calc R . .
C40 C 0.42156(10) 0.10822(8) 0.1214(2) 0.0654(8) Uani 1 1 d . . .
H40 H 0.4474 0.1214 0.1408 0.078 Uiso 1 1 calc R . .
C41 C 0.43985(12) 0.07744(9) 0.0801(3) 0.0801(10) Uani 1 1 d . . .
H41A H 0.4594 0.0848 0.0384 0.096 Uiso 1 1 calc R . .
H41B H 0.4149 0.0645 0.0583 0.096 Uiso 1 1 calc R . .
C42 C 0.46676(14) 0.05463(11) 0.1351(4) 0.1045(15) Uani 1 1 d . . .
H42A H 0.4759 0.0340 0.1084 0.125 Uiso 1 1 calc R . .
H42B H 0.4941 0.0665 0.1511 0.125 Uiso 1 1 calc R . .
C43 C 0.43909(16) 0.04521(11) 0.2051(3) 0.1074(16) Uani 1 1 d . . .
H43A H 0.4146 0.0301 0.1898 0.129 Uiso 1 1 calc R . .
H43B H 0.4582 0.0329 0.2410 0.129 Uiso 1 1 calc R . .
C44 C 0.41942(17) 0.07596(12) 0.2447(3) 0.1025(14) Uani 1 1 d . . .
H44A H 0.4439 0.0895 0.2663 0.123 Uiso 1 1 calc R . .
H44B H 0.4001 0.0685 0.2866 0.123 Uiso 1 1 calc R . .
C45 C 0.39181(13) 0.09805(9) 0.1901(2) 0.0741(9) Uani 1 1 d . . .
H45A H 0.3813 0.1184 0.2166 0.089 Uiso 1 1 calc R . .
H45B H 0.3654 0.0855 0.1723 0.089 Uiso 1 1 calc R . .
C46 C 0.37425(10) 0.16206(7) 0.09345(18) 0.0555(7) Uani 1 1 d . . .
H46 H 0.3489 0.1556 0.1269 0.067 Uiso 1 1 calc R . .
C47 C 0.40636(11) 0.18465(9) 0.1395(2) 0.0714(8) Uani 1 1 d . . .
H47A H 0.4325 0.1906 0.1083 0.086 Uiso 1 1 calc R . .
H47B H 0.4171 0.1723 0.1843 0.086 Uiso 1 1 calc R . .
C48 C 0.38141(14) 0.21731(9) 0.1648(2) 0.0820(10) Uani 1 1 d . . .
H48A H 0.3576 0.2113 0.2010 0.098 Uiso 1 1 calc R . .
H48B H 0.4026 0.2323 0.1909 0.098 Uiso 1 1 calc R . .
C49 C 0.36084(15) 0.23591(9) 0.0979(2) 0.0832(11) Uani 1 1 d . . .
H49A H 0.3850 0.2450 0.0659 0.100 Uiso 1 1 calc R . .
H49B H 0.3431 0.2550 0.1168 0.100 Uiso 1 1 calc R . .
C50 C 0.33085(13) 0.21328(8) 0.0498(2) 0.0770(9) Uani 1 1 d . . .
H50A H 0.3210 0.2258 0.0046 0.092 Uiso 1 1 calc R . .
H50B H 0.3040 0.2072 0.0791 0.092 Uiso 1 1 calc R . .
C51 C 0.35502(11) 0.18107(7) 0.0249(2) 0.0653(8) Uani 1 1 d . . .
H51A H 0.3795 0.1869 -0.0100 0.078 Uiso 1 1 calc R . .
H51B H 0.3339 0.1664 -0.0022 0.078 Uiso 1 1 calc R . .
H7WA H 0.0311(18) 0.1403(15) 0.605(3) 0.125(17) Uiso 1 1 d . . .
H7WB H 0.043(2) 0.1349(19) 0.688(5) 0.18(3) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag



O1 C1 1.240(3) . ?
O2 C1 1.246(3) . ?
O3 C8 1.255(3) . ?
O4 C8 1.241(4) . ?
O5 C13 1.241(3) . ?
O6 C13 1.226(4) . ?
O7 H7WA 1.06(6) . ?
O7 H7WB 0.99(9) . ?
N1 C22 1.506(3) . ?
N1 C16 1.507(3) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N2 C34 1.496(3) . ?
N2 C28 1.497(3) . ?
N2 H2A 0.9000 . ?
N2 H2B 0.9000 . ?
N3 C40 1.493(4) . ?
N3 C46 1.495(4) . ?
N3 H3A 0.9000 . ?
N3 H3B 0.9000 . ?
C1 O1 1.240(3) 1 ?
C1 O2 1.246(3) 1 ?
C1 C2 1.528(4) . ?
C2 C3 1.518(4) . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C3 C14 1.392(4) . ?
C3 C4 1.401(4) . ?
C4 C6 1.396(4) . ?
C4 C5 1.516(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C9 1.406(4) . ?
C6 C7 1.515(4) . ?
C7 C8 1.528(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C11 1.388(4) . ?
C9 C10 1.515(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C14 1.411(4) . ?
C11 C12 1.509(4) . ?
C12 C13 1.518(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O5 1.241(3) 1 ?
C14 C15 1.509(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.502(4) . ?
C16 C21 1.505(4) . ?
C16 H16 0.9800 . ?
C17 C18 1.524(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.506(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.508(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.523(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C27 1.507(4) . ?
C22 C23 1.517(4) . ?
C22 H22 0.9800 . ?
C23 C24 1.519(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.499(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.499(5) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.533(5) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.510(5) . ?
C28 C33 1.517(4) . ?
C28 H28 0.9800 . ?
C29 C30 1.540(5) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.510(7) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.502(6) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.516(5) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C39 1.515(4) . ?
C34 C35 1.518(4) . ?
C34 H34 0.9800 . ?
C35 C36 1.521(4) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.516(4) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C38 1.509(5) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.528(5) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 C41 1.503(5) . ?
C40 C45 1.536(5) . ?
C40 H40 0.9800 . ?
C41 C42 1.530(6) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C43 1.512(7) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 C44 1.503(7) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 C45 1.520(5) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 C51 1.516(4) . ?
C46 C47 1.522(4) . ?
C46 H46 0.9800 . ?
C47 C48 1.539(5) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C48 C49 1.502(6) . ?
C48 H48A 0.9700 . ?
C48 H48B 0.9700 . ?
C49 C50 1.505(5) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 C51 1.511(5) . ?
C50 H50A 0.9700 . ?
C50 H50B 0.9700 . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?

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




H7WA O7 H7WB 93(5) . . ?
C22 N1 C16 115.56(19) . . ?
C22 N1 H1A 108.4 . . ?
C16 N1 H1A 108.4 . . ?
C22 N1 H1B 108.4 . . ?
C16 N1 H1B 108.4 . . ?
H1A N1 H1B 107.5 . . ?
C34 N2 C28 116.7(2) . . ?
C34 N2 H2A 108.1 . . ?
C28 N2 H2A 108.1 . . ?
C34 N2 H2B 108.1 . . ?
C28 N2 H2B 108.1 . . ?
H2A N2 H2B 107.3 . . ?
C40 N3 C46 118.8(2) . . ?
C40 N3 H3A 107.6 . . ?
C46 N3 H3A 107.6 . . ?
C40 N3 H3B 107.6 . . ?
C46 N3 H3B 107.6 . . ?
H3A N3 H3B 107.0 . . ?
O1 C1 O2 124.3(3) 1 . ?
O1 C1 O2 124.3(3) . . ?
O1 C1 O2 124.3(3) 1 1 ?
O1 C1 O2 124.3(3) . 1 ?
O1 C1 C2 120.4(2) 1 . ?
O1 C1 C2 120.4(2) . . ?
O2 C1 C2 115.2(2) . . ?
O2 C1 C2 115.2(2) 1 . ?
C3 C2 C1 116.0(2) . . ?
C3 C2 H2C 108.3 . . ?
C1 C2 H2C 108.3 . . ?
C3 C2 H2D 108.3 . . ?
C1 C2 H2D 108.3 . . ?
H2C C2 H2D 107.4 . . ?
C14 C3 C4 120.1(2) . . ?
C14 C3 C2 120.1(2) . . ?
C4 C3 C2 119.9(3) . . ?
C6 C4 C3 119.9(2) . . ?
C6 C4 C5 120.1(3) . . ?
C3 C4 C5 120.0(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 C9 120.1(2) . . ?
C4 C6 C7 119.6(3) . . ?
C9 C6 C7 120.2(3) . . ?
C6 C7 C8 118.4(2) . . ?
C6 C7 H7A 107.7 . . ?
C8 C7 H7A 107.7 . . ?
C6 C7 H7B 107.7 . . ?
C8 C7 H7B 107.7 . . ?
H7A C7 H7B 107.1 . . ?
O4 C8 O3 125.0(3) . . ?
O4 C8 C7 119.7(2) . . ?
O3 C8 C7 115.3(3) . . ?
C11 C9 C6 120.0(2) . . ?
C11 C9 C10 121.1(3) . . ?
C6 C9 C10 118.8(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 C14 119.8(2) . . ?
C9 C11 C12 121.3(3) . . ?
C14 C11 C12 118.9(2) . . ?
C11 C12 C13 117.4(2) . . ?
C11 C12 H12A 108.0 . . ?
C13 C12 H12A 108.0 . . ?
C11 C12 H12B 108.0 . . ?
C13 C12 H12B 108.0 . . ?
H12A C12 H12B 107.2 . . ?
O6 C13 O5 122.7(3) . 1 ?
O6 C13 O5 122.7(3) . . ?
O6 C13 C12 116.0(3) . . ?
O5 C13 C12 121.1(2) 1 . ?
O5 C13 C12 121.1(2) . . ?
C3 C14 C11 120.1(2) . . ?
C3 C14 C15 121.4(3) . . ?
C11 C14 C15 118.5(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 111.9(3) . . ?
C17 C16 N1 112.1(2) . . ?
C21 C16 N1 108.4(2) . . ?
C17 C16 H16 108.1 . . ?
C21 C16 H16 108.1 . . ?
N1 C16 H16 108.1 . . ?
C16 C17 C18 110.8(3) . . ?
C16 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C19 C18 C17 111.9(3) . . ?
C19 C18 H18A 109.2 . . ?
C17 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
C17 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 C20 111.3(3) . . ?
C18 C19 H19A 109.4 . . ?
C20 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
C20 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C19 C20 C21 110.9(3) . . ?
C19 C20 H20A 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C16 C21 C20 111.0(3) . . ?
C16 C21 H21A 109.4 . . ?
C20 C21 H21A 109.4 . . ?
C16 C21 H21B 109.4 . . ?
C20 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
N1 C22 C27 109.7(2) . . ?
N1 C22 C23 111.9(2) . . ?
C27 C22 C23 110.5(3) . . ?
N1 C22 H22 108.2 . . ?
C27 C22 H22 108.2 . . ?
C23 C22 H22 108.2 . . ?
C22 C23 C24 111.0(3) . . ?
C22 C23 H23A 109.4 . . ?
C24 C23 H23A 109.4 . . ?
C22 C23 H23B 109.4 . . ?
C24 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C25 C24 C23 112.8(3) . . ?
C25 C24 H24A 109.0 . . ?
C23 C24 H24A 109.0 . . ?
C25 C24 H24B 109.0 . . ?
C23 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C26 C25 C24 111.0(3) . . ?
C26 C25 H25A 109.4 . . ?
C24 C25 H25A 109.4 . . ?
C26 C25 H25B 109.4 . . ?
C24 C25 H25B 109.4 . . ?
H25A C25 H25B 108.0 . . ?
C25 C26 C27 111.4(3) . . ?
C25 C26 H26A 109.3 . . ?
C27 C26 H26A 109.3 . . ?
C25 C26 H26B 109.3 . . ?
C27 C26 H26B 109.3 . . ?
H26A C26 H26B 108.0 . . ?
C22 C27 C26 110.6(3) . . ?
C22 C27 H27A 109.5 . . ?
C26 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 108.1 . . ?
N2 C28 C29 112.0(2) . . ?
N2 C28 C33 109.8(2) . . ?
C29 C28 C33 110.8(3) . . ?
N2 C28 H28 108.1 . . ?
C29 C28 H28 108.1 . . ?
C33 C28 H28 108.1 . . ?
C28 C29 C30 110.0(3) . . ?
C28 C29 H29A 109.7 . . ?
C30 C29 H29A 109.7 . . ?
C28 C29 H29B 109.7 . . ?
C30 C29 H29B 109.7 . . ?
H29A C29 H29B 108.2 . . ?
C31 C30 C29 110.9(4) . . ?
C31 C30 H30A 109.5 . . ?
C29 C30 H30A 109.5 . . ?
C31 C30 H30B 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 108.1 . . ?
C32 C31 C30 111.1(4) . . ?
C32 C31 H31A 109.4 . . ?
C30 C31 H31A 109.4 . . ?
C32 C31 H31B 109.4 . . ?
C30 C31 H31B 109.4 . . ?
H31A C31 H31B 108.0 . . ?
C31 C32 C33 112.1(3) . . ?
C31 C32 H32A 109.2 . . ?
C33 C32 H32A 109.2 . . ?
C31 C32 H32B 109.2 . . ?
C33 C32 H32B 109.2 . . ?
H32A C32 H32B 107.9 . . ?
C32 C33 C28 110.9(3) . . ?
C32 C33 H33A 109.5 . . ?
C28 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C28 C33 H33B 109.5 . . ?
H33A C33 H33B 108.0 . . ?
N2 C34 C39 109.3(2) . . ?
N2 C34 C35 111.5(2) . . ?
C39 C34 C35 110.8(2) . . ?
N2 C34 H34 108.4 . . ?
C39 C34 H34 108.4 . . ?
C35 C34 H34 108.4 . . ?
C34 C35 C36 111.1(3) . . ?
C34 C35 H35A 109.4 . . ?
C36 C35 H35A 109.4 . . ?
C34 C35 H35B 109.4 . . ?
C36 C35 H35B 109.4 . . ?
H35A C35 H35B 108.0 . . ?
C37 C36 C35 111.6(3) . . ?
C37 C36 H36A 109.3 . . ?
C35 C36 H36A 109.3 . . ?
C37 C36 H36B 109.3 . . ?
C35 C36 H36B 109.3 . . ?
H36A C36 H36B 108.0 . . ?
C38 C37 C36 111.3(3) . . ?
C38 C37 H37A 109.4 . . ?
C36 C37 H37A 109.4 . . ?
C38 C37 H37B 109.4 . . ?
C36 C37 H37B 109.4 . . ?
H37A C37 H37B 108.0 . . ?
C37 C38 C39 112.4(3) . . ?
C37 C38 H38A 109.1 . . ?
C39 C38 H38A 109.1 . . ?
C37 C38 H38B 109.1 . . ?
C39 C38 H38B 109.1 . . ?
H38A C38 H38B 107.9 . . ?
C34 C39 C38 110.6(2) . . ?
C34 C39 H39A 109.5 . . ?
C38 C39 H39A 109.5 . . ?
C34 C39 H39B 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 108.1 . . ?
N3 C40 C41 108.9(3) . . ?
N3 C40 C45 111.8(2) . . ?
C41 C40 C45 111.7(3) . . ?
N3 C40 H40 108.1 . . ?
C41 C40 H40 108.1 . . ?
C45 C40 H40 108.1 . . ?
C40 C41 C42 110.7(4) . . ?
C40 C41 H41A 109.5 . . ?
C42 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
C42 C41 H41B 109.5 . . ?
H41A C41 H41B 108.1 . . ?
C43 C42 C41 111.6(3) . . ?
C43 C42 H42A 109.3 . . ?
C41 C42 H42A 109.3 . . ?
C43 C42 H42B 109.3 . . ?
C41 C42 H42B 109.3 . . ?
H42A C42 H42B 108.0 . . ?
C44 C43 C42 112.5(3) . . ?
C44 C43 H43A 109.1 . . ?
C42 C43 H43A 109.1 . . ?
C44 C43 H43B 109.1 . . ?
C42 C43 H43B 109.1 . . ?
H43A C43 H43B 107.8 . . ?
C43 C44 C45 112.0(4) . . ?
C43 C44 H44A 109.2 . . ?
C45 C44 H44A 109.2 . . ?
C43 C44 H44B 109.2 . . ?
C45 C44 H44B 109.2 . . ?
H44A C44 H44B 107.9 . . ?
C44 C45 C40 109.2(3) . . ?
C44 C45 H45A 109.8 . . ?
C40 C45 H45A 109.8 . . ?
C44 C45 H45B 109.8 . . ?
C40 C45 H45B 109.8 . . ?
H45A C45 H45B 108.3 . . ?
N3 C46 C51 108.5(2) . . ?
N3 C46 C47 113.0(2) . . ?
C51 C46 C47 111.2(2) . . ?
N3 C46 H46 108.0 . . ?
C51 C46 H46 108.0 . . ?
C47 C46 H46 108.0 . . ?
C46 C47 C48 109.7(3) . . ?
C46 C47 H47A 109.7 . . ?
C48 C47 H47A 109.7 . . ?
C46 C47 H47B 109.7 . . ?
C48 C47 H47B 109.7 . . ?
H47A C47 H47B 108.2 . . ?
C49 C48 C47 111.9(3) . . ?
C49 C48 H48A 109.2 . . ?
C47 C48 H48A 109.2 . . ?
C49 C48 H48B 109.2 . . ?
C47 C48 H48B 109.2 . . ?
H48A C48 H48B 107.9 . . ?
C48 C49 C50 112.5(3) . . ?
C48 C49 H49A 109.1 . . ?
C50 C49 H49A 109.1 . . ?
C48 C49 H49B 109.1 . . ?
C50 C49 H49B 109.1 . . ?
H49A C49 H49B 107.8 . . ?
C49 C50 C51 112.0(3) . . ?
C49 C50 H50A 109.2 . . ?
C51 C50 H50A 109.2 . . ?
C49 C50 H50B 109.2 . . ?
C51 C50 H50B 109.2 . . ?
H50A C50 H50B 107.9 . . ?
C50 C51 C46 111.1(3) . . ?
C50 C51 H51A 109.4 . . ?
C46 C51 H51A 109.4 . . ?
C50 C51 H51B 109.4 . . ?
C46 C51 H51B 109.4 . . ?
H51A C51 H51B 108.0 . . ?

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
O7 H7WB O3 0.99(9) 1.91(9) 2.827(4) 153(6) 3
O7 H7WA O6 1.06(6) 1.77(6) 2.748(4) 152(4) 8_444
N3 H3B O6 0.90 2.38 3.041(4) 130.8 16_444
N3 H3B O5 0.90 2.22 3.104(3) 168.5 16_444
N3 H3A O3 0.90 1.93 2.767(3) 154.2 10_554
N2 H2B O4 0.90 1.90 2.774(3) 164.8 10_554
N2 H2A O2 0.90 1.78 2.673(3) 172.3 1
N1 H1B O1 0.90 1.89 2.775(3) 168.2 1
N1 H1A O5 0.90 1.91 2.782(3) 163.9 1

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.023
_database_code_depnum_ccdc_archive 'CCDC 929288'
