# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_1273
_database_code_depnum_ccdc_archive 'CCDC 1496575'
_audit_update_record             
;
2016-07-28 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;
_audit_creation_date             
;
'Tue Oct 14 18:41:24 2014'
;
_audit_creation_method           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_chemical_name_systematic        
((3'S,3a'R,4'R,5'R)-4',5'-di-tert-butoxytetrahydro-3'H-spiro[cyclopropane-1,2'-pyrrolo[1,2-b]isoxazol]-3'-yl)methanol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H31 N O4'
_chemical_formula_sum            'C17 H31 N O4'
_chemical_formula_weight         313.43
_chemical_absolute_configuration syn
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   17.6430(10)
_cell_length_b                   16.1440(10)
_cell_length_c                   6.6010(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1880.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2322
_cell_measurement_theta_min      4.9960
_cell_measurement_theta_max      69.5550

_exptl_crystal_description       prismatic
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96019
_exptl_absorpt_correction_T_max  0.97530
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1241
_diffrn_reflns_number            5913
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         5.013
_diffrn_reflns_theta_max         70.844
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.991
_reflns_number_total             3079
_reflns_number_gt                2442
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.532
_reflns_Friedel_fraction_max     0.701
_reflns_Friedel_fraction_full    0.747
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   76.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       46.2824  125.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega  -16.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       46.2824  -57.0000  -60.0000 81

#__ type_ start__ end____ width___ exp.time_
  3 omega  -92.00  -45.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000   30.0000 47

#__ type_ start__ end____ width___ exp.time_
  4 omega  -64.00  -27.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   45.0000   60.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega   32.00   57.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega   24.00   49.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega   35.00   68.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000   90.0000 33

#__ type_ start__ end____ width___ exp.time_
  8 omega   17.00  106.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -94.0000 -150.0000 89

#__ type_ start__ end____ width___ exp.time_
  9 omega -122.00  -47.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.2824  -19.0000 -120.0000 75
;

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SIR2004 J.Appl.Cryst.38,381-388'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0428P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 x determined using 725 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_number_reflns         3079
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1068
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.69296(14) 0.27327(14) -0.0737(4) 0.0236(6) Uani 1 1 d . . . . .
O1 O 0.71761(11) 0.35721(12) -0.0119(4) 0.0254(5) Uani 1 1 d . . . . .
O2 O 0.61653(12) 0.27236(13) 0.5645(3) 0.0281(5) Uani 1 1 d . . . . .
H2 H 0.6330 0.2762 0.6804 0.042 Uiso 1 1 calc R U . . .
O3 O 0.67432(12) 0.09642(11) 0.1317(4) 0.0292(6) Uani 1 1 d . . . . .
O4 O 0.81814(11) 0.24690(12) 0.2505(4) 0.0265(5) Uani 1 1 d . . . . .
C1 C 0.64868(16) 0.24186(16) 0.1069(5) 0.0198(6) Uani 1 1 d . . . . .
H1 H 0.6028 0.2147 0.0561 0.024 Uiso 1 1 calc R U . . .
C2 C 0.62418(17) 0.32046(17) 0.2241(5) 0.0212(7) Uani 1 1 d . . . . .
H2A H 0.5687 0.3226 0.2296 0.025 Uiso 1 1 calc R U . . .
C3 C 0.65233(17) 0.38798(17) 0.0847(5) 0.0236(7) Uani 1 1 d . . . . .
C4 C 0.76273(17) 0.2231(2) -0.0859(5) 0.0262(7) Uani 1 1 d . . . . .
H4A H 0.8047 0.2570 -0.1325 0.031 Uiso 1 1 calc R U . . .
H4B H 0.7558 0.1779 -0.1808 0.031 Uiso 1 1 calc R U . . .
C5 C 0.77939(16) 0.18940(18) 0.1244(5) 0.0237(7) Uani 1 1 d . . . . .
H5 H 0.8074 0.1371 0.1159 0.028 Uiso 1 1 calc R U . . .
C6 C 0.69869(17) 0.17492(16) 0.2075(5) 0.0209(7) Uani 1 1 d . . . . .
H6 H 0.6968 0.1776 0.3558 0.025 Uiso 1 1 calc R U . . .
C7 C 0.6528(2) 0.47874(18) 0.1227(6) 0.0338(8) Uani 1 1 d . . . . .
H7A H 0.6967 0.5100 0.0783 0.041 Uiso 1 1 calc R U . . .
H7B H 0.6295 0.4986 0.2467 0.041 Uiso 1 1 calc R U . . .
C8 C 0.60122(19) 0.44264(18) -0.0389(6) 0.0320(8) Uani 1 1 d . . . . .
H8A H 0.5473 0.4407 -0.0111 0.038 Uiso 1 1 calc R U . . .
H8B H 0.6145 0.4521 -0.1796 0.038 Uiso 1 1 calc R U . . .
C9 C 0.65541(17) 0.32925(18) 0.4368(5) 0.0241(7) Uani 1 1 d . . . . .
H9A H 0.7093 0.3174 0.4375 0.029 Uiso 1 1 calc R U . . .
H9B H 0.6479 0.3854 0.4851 0.029 Uiso 1 1 calc R U . . .
C10 C 0.64841(17) 0.03524(18) 0.2760(6) 0.0281(8) Uani 1 1 d . . . . .
C11 C 0.58506(19) 0.0699(2) 0.4067(7) 0.0474(11) Uani 1 1 d . . . . .
H11A H 0.5687 0.0283 0.5012 0.071 Uiso 1 1 calc R U . . .
H11B H 0.6032 0.1174 0.4794 0.071 Uiso 1 1 calc R U . . .
H11C H 0.5432 0.0857 0.3221 0.071 Uiso 1 1 calc R U . . .
C12 C 0.6207(2) -0.03450(19) 0.1408(7) 0.0390(10) Uani 1 1 d . . . . .
H12A H 0.6020 -0.0790 0.2231 0.059 Uiso 1 1 calc R U . . .
H12B H 0.5808 -0.0145 0.0550 0.059 Uiso 1 1 calc R U . . .
H12C H 0.6619 -0.0541 0.0586 0.059 Uiso 1 1 calc R U . . .
C13 C 0.7143(2) 0.0068(2) 0.4081(6) 0.0397(9) Uani 1 1 d . . . . .
H13A H 0.6967 -0.0337 0.5034 0.060 Uiso 1 1 calc R U . . .
H13B H 0.7530 -0.0171 0.3242 0.060 Uiso 1 1 calc R U . . .
H13C H 0.7348 0.0535 0.4799 0.060 Uiso 1 1 calc R U . . .
C14 C 0.89776(17) 0.2308(2) 0.2884(5) 0.0267(8) Uani 1 1 d . . . . .
C15 C 0.92325(18) 0.3059(2) 0.4059(7) 0.0398(10) Uani 1 1 d . . . . .
H15A H 0.9761 0.3007 0.4383 0.060 Uiso 1 1 calc R U . . .
H15B H 0.9155 0.3547 0.3255 0.060 Uiso 1 1 calc R U . . .
H15C H 0.8944 0.3101 0.5288 0.060 Uiso 1 1 calc R U . . .
C16 C 0.94219(18) 0.2235(2) 0.0905(6) 0.0389(9) Uani 1 1 d . . . . .
H16A H 0.9946 0.2128 0.1202 0.058 Uiso 1 1 calc R U . . .
H16B H 0.9220 0.1787 0.0113 0.058 Uiso 1 1 calc R U . . .
H16C H 0.9379 0.2743 0.0158 0.058 Uiso 1 1 calc R U . . .
C17 C 0.90716(18) 0.1531(2) 0.4147(6) 0.0361(9) Uani 1 1 d . . . . .
H17A H 0.9601 0.1433 0.4385 0.054 Uiso 1 1 calc R U . . .
H17B H 0.8816 0.1601 0.5420 0.054 Uiso 1 1 calc R U . . .
H17C H 0.8858 0.1068 0.3437 0.054 Uiso 1 1 calc R U . . .


_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
N1 C4 1.475(4) . ?
N1 O1 1.480(3) . ?
N1 C1 1.513(4) . ?
O1 C3 1.407(4) . ?
O2 C9 1.423(4) . ?
O2 H2 0.8200 . ?
O3 C6 1.429(3) . ?
O3 C10 1.446(4) . ?
O4 C5 1.422(4) . ?
O4 C14 1.450(4) . ?
C1 C2 1.548(4) . ?
C1 C6 1.545(4) . ?
C1 H1 0.9800 . ?
C2 C3 1.511(4) . ?
C2 C9 1.515(5) . ?
C2 H2A 0.9800 . ?
C3 C7 1.487(4) . ?
C3 C8 1.502(4) . ?
C4 C5 1.520(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.544(4) . ?
C5 H5 0.9800 . ?
C6 H6 0.9800 . ?
C7 C8 1.518(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C12 1.518(5) . ?
C10 C11 1.519(5) . ?
C10 C13 1.524(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.508(4) . ?
C14 C17 1.514(5) . ?
C14 C16 1.528(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C4 N1 O1 105.8(2) . . ?
C4 N1 C1 106.9(2) . . ?
O1 N1 C1 104.0(2) . . ?
C3 O1 N1 101.97(19) . . ?
C9 O2 H2 109.5 . . ?
C6 O3 C10 118.0(3) . . ?
C5 O4 C14 116.7(2) . . ?
N1 C1 C2 105.3(2) . . ?
N1 C1 C6 106.2(2) . . ?
C2 C1 C6 121.2(3) . . ?
N1 C1 H1 107.9 . . ?
C2 C1 H1 107.9 . . ?
C6 C1 H1 107.9 . . ?
C3 C2 C9 112.2(2) . . ?
C3 C2 C1 101.2(2) . . ?
C9 C2 C1 116.0(2) . . ?
C3 C2 H2A 109.0 . . ?
C9 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
O1 C3 C7 114.8(3) . . ?
O1 C3 C8 116.9(3) . . ?
C7 C3 C8 61.1(2) . . ?
O1 C3 C2 106.9(2) . . ?
C7 C3 C2 127.6(3) . . ?
C8 C3 C2 123.9(3) . . ?
N1 C4 C5 107.9(3) . . ?
N1 C4 H4A 110.1 . . ?
C5 C4 H4A 110.1 . . ?
N1 C4 H4B 110.1 . . ?
C5 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
O4 C5 C4 113.2(2) . . ?
O4 C5 C6 109.5(3) . . ?
C4 C5 C6 101.6(2) . . ?
O4 C5 H5 110.7 . . ?
C4 C5 H5 110.7 . . ?
C6 C5 H5 110.7 . . ?
O3 C6 C5 106.7(2) . . ?
O3 C6 C1 107.3(2) . . ?
C5 C6 C1 105.5(2) . . ?
O3 C6 H6 112.3 . . ?
C5 C6 H6 112.3 . . ?
C1 C6 H6 112.3 . . ?
C3 C7 C8 60.0(2) . . ?
C3 C7 H7A 117.8 . . ?
C8 C7 H7A 117.8 . . ?
C3 C7 H7B 117.8 . . ?
C8 C7 H7B 117.8 . . ?
H7A C7 H7B 114.9 . . ?
C3 C8 C7 59.0(2) . . ?
C3 C8 H8A 117.9 . . ?
C7 C8 H8A 117.9 . . ?
C3 C8 H8B 117.9 . . ?
C7 C8 H8B 117.9 . . ?
H8A C8 H8B 115.0 . . ?
O2 C9 C2 108.3(2) . . ?
O2 C9 H9A 110.0 . . ?
C2 C9 H9A 110.0 . . ?
O2 C9 H9B 110.0 . . ?
C2 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
O3 C10 C12 102.8(3) . . ?
O3 C10 C11 110.8(3) . . ?
C12 C10 C11 111.7(3) . . ?
O3 C10 C13 109.9(2) . . ?
C12 C10 C13 111.0(3) . . ?
C11 C10 C13 110.3(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 C15 103.5(2) . . ?
O4 C14 C17 110.5(3) . . ?
C15 C14 C17 110.5(3) . . ?
O4 C14 C16 111.3(3) . . ?
C15 C14 C16 110.4(3) . . ?
C17 C14 C16 110.5(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 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.044

_shelxl_version_number           2014/6



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1272
_database_code_depnum_ccdc_archive 'CCDC 1496576'
_audit_update_record             
;
2016-07-28 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;
_audit_creation_date             
;
'Tue Oct 14 14:57:20 2014'
;
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_chemical_name_systematic        
;
((3'R,3a'R,4'R,5'R)-4',5'-di-tert-butoxytetrahydro-3'H-spiro
[cyclopropane-1,2'-pyrrolo[1,2-b]isoxazol]-3'-yl)methanol
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H31 N O4'
_chemical_formula_sum            'C17 H31 N O4'
_chemical_formula_weight         313.43
_chemical_absolute_configuration syn

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.030(1)
_cell_length_b                   16.334(1)
_cell_length_c                   18.224(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1795.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4102
_cell_measurement_theta_min      4.8380
_cell_measurement_theta_max      70.3780
_cell_measurement_wavelength     1.54184

_exptl_crystal_description       prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9552
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1241
_diffrn_reflns_number            5696
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.853
_diffrn_reflns_theta_max         70.654
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.9972
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_point_group_measured_fraction_full 0.864
_reflns_number_total             2886
_reflns_number_gt                2603
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.483
_reflns_Friedel_fraction_max     0.651
_reflns_Friedel_fraction_full    0.688
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -116.00  -89.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -46.2824 -125.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega   73.00  111.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       46.2824  125.0000  -30.0000 38

#__ type_ start__ end____ width___ exp.time_
  3 omega  -22.00   31.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       46.2824  -57.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
  4 omega   36.00   70.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       46.2824  -57.0000   60.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega   65.00  166.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919   15.0000 -120.0000 101

#__ type_ start__ end____ width___ exp.time_
  6 omega   35.00   72.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -45.0000    0.0000 37

#__ type_ start__ end____ width___ exp.time_
  7 omega   44.00   72.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -45.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
  8 omega   18.00   76.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -94.0000   30.0000 58

#__ type_ start__ end____ width___ exp.time_
  9 omega -117.00  -39.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -46.2824  -37.0000   90.0000 78

;

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SIR2004 J.Appl.Cryst.38,381-388'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0336P)²+0.7703P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0049(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 813 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(16)
_refine_ls_number_reflns         2886
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0921
_refine_ls_wR_factor_gt          0.0786
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.0947(3) 0.75198(12) 0.33410(11) 0.0211(5) Uani 1 1 d . . . . .
O1 O 1.0073(3) 0.67517(10) 0.30088(9) 0.0229(4) Uani 1 1 d . . . . .
O2 O 0.3953(3) 0.67364(11) 0.43157(10) 0.0261(4) Uani 1 1 d . . . . .
H2 H 0.3114 0.6821 0.3970 0.039 Uiso 1 1 calc R U . . .
O3 O 0.8356(3) 0.79913(10) 0.19751(9) 0.0247(4) Uani 1 1 d . . . . .
O4 O 0.9666(3) 0.94132(11) 0.34307(10) 0.0251(4) Uani 1 1 d . . . . .
C1 C 0.8909(4) 0.79509(15) 0.36302(13) 0.0187(5) Uani 1 1 d . . . . .
H1 H 0.9174 0.8125 0.4137 0.022 Uiso 1 1 calc R U . . .
C2 C 0.7049(4) 0.73154(15) 0.36165(13) 0.0181(5) Uani 1 1 d . . . . .
H2A H 0.6079 0.7429 0.3197 0.022 Uiso 1 1 calc R U . . .
C3 C 0.8299(4) 0.65324(15) 0.34710(14) 0.0202(5) Uani 1 1 d . . . . .
C4 C 1.1717(5) 0.80071(16) 0.27059(14) 0.0229(6) Uani 1 1 d . . . . .
H4A H 1.2279 0.7649 0.2324 0.027 Uiso 1 1 calc R U . . .
H4B H 1.2896 0.8375 0.2854 0.027 Uiso 1 1 calc R U . . .
C5 C 0.9741(5) 0.84915(16) 0.24246(13) 0.0216(6) Uani 1 1 d . . . . .
H5 H 1.0219 0.8984 0.2162 0.026 Uiso 1 1 calc R U . . .
C6 C 0.8557(4) 0.87116(14) 0.31439(13) 0.0199(5) Uani 1 1 d . . . . .
H6 H 0.6977 0.8820 0.3063 0.024 Uiso 1 1 calc R U . . .
C7 C 0.7369(5) 0.57104(16) 0.33210(16) 0.0297(7) Uani 1 1 d . . . . .
H7A H 0.8054 0.5387 0.2936 0.036 Uiso 1 1 calc R U . . .
H7B H 0.5779 0.5640 0.3369 0.036 Uiso 1 1 calc R U . . .
C8 C 0.8694(5) 0.58598(16) 0.40140(16) 0.0294(6) Uani 1 1 d . . . . .
H8A H 0.7896 0.5881 0.4476 0.035 Uiso 1 1 calc R U . . .
H8B H 1.0173 0.5628 0.4043 0.035 Uiso 1 1 calc R U . . .
C9 C 0.5667(4) 0.73293(16) 0.43138(14) 0.0232(6) Uani 1 1 d . . . . .
H9A H 0.6631 0.7233 0.4731 0.028 Uiso 1 1 calc R U . . .
H9B H 0.5016 0.7869 0.4371 0.028 Uiso 1 1 calc R U . . .
C10 C 0.8302(5) 1.00541(16) 0.37573(15) 0.0274(6) Uani 1 1 d . . . . .
C11 C 0.6926(6) 0.97100(17) 0.43843(16) 0.0336(7) Uani 1 1 d . . . . .
H11A H 0.6038 1.0138 0.4594 0.050 Uiso 1 1 calc R U . . .
H11B H 0.5978 0.9284 0.4202 0.050 Uiso 1 1 calc R U . . .
H11C H 0.7894 0.9490 0.4753 0.050 Uiso 1 1 calc R U . . .
C12 C 1.0001(7) 1.06582(19) 0.40354(19) 0.0454(9) Uani 1 1 d . . . . .
H12A H 0.9260 1.1111 0.4264 0.068 Uiso 1 1 calc R U . . .
H12B H 1.0947 1.0394 0.4387 0.068 Uiso 1 1 calc R U . . .
H12C H 1.0878 1.0853 0.3632 0.068 Uiso 1 1 calc R U . . .
C13 C 0.6838(6) 1.04478(17) 0.31798(16) 0.0348(7) Uani 1 1 d . . . . .
H13A H 0.5952 1.0868 0.3403 0.052 Uiso 1 1 calc R U . . .
H13B H 0.7750 1.0685 0.2804 0.052 Uiso 1 1 calc R U . . .
H13C H 0.5887 1.0040 0.2967 0.052 Uiso 1 1 calc R U . . .
C14 C 0.7731(4) 0.83178(16) 0.12678(13) 0.0217(6) Uani 1 1 d . . . . .
C15 C 0.6277(5) 0.76510(17) 0.09456(14) 0.0288(6) Uani 1 1 d . . . . .
H15A H 0.5773 0.7815 0.0468 0.043 Uiso 1 1 calc R U . . .
H15B H 0.7114 0.7153 0.0905 0.043 Uiso 1 1 calc R U . . .
H15C H 0.5021 0.7563 0.1260 0.043 Uiso 1 1 calc R U . . .
C16 C 0.9784(5) 0.84438(17) 0.07962(14) 0.0292(7) Uani 1 1 d . . . . .
H16A H 0.9355 0.8661 0.0328 0.044 Uiso 1 1 calc R U . . .
H16B H 1.0767 0.8821 0.1035 0.044 Uiso 1 1 calc R U . . .
H16C H 1.0525 0.7929 0.0728 0.044 Uiso 1 1 calc R U . . .
C17 C 0.6426(5) 0.91080(16) 0.13545(15) 0.0283(6) Uani 1 1 d . . . . .
H17A H 0.6028 0.9314 0.0879 0.042 Uiso 1 1 calc R U . . .
H17B H 0.5106 0.9003 0.1634 0.042 Uiso 1 1 calc R U . . .
H17C H 0.7320 0.9506 0.1606 0.042 Uiso 1 1 calc R U . . .


_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
N1 C4 1.479(3) . ?
N1 O1 1.490(3) . ?
N1 C1 1.511(3) . ?
O1 C3 1.408(3) . ?
O2 C9 1.416(3) . ?
O2 H2 0.8200 . ?
O3 C5 1.427(3) . ?
O3 C14 1.445(3) . ?
O4 C6 1.426(3) . ?
O4 C10 1.458(3) . ?
C1 C2 1.529(3) . ?
C1 C6 1.541(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.508(3) . ?
C2 C9 1.520(3) . ?
C2 H2A 0.9800 . ?
C3 C7 1.481(3) . ?
C3 C8 1.498(4) . ?
C4 C5 1.520(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.535(4) . ?
C5 H5 0.9800 . ?
C6 H6 0.9800 . ?
C7 C8 1.514(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C12 1.510(4) . ?
C10 C13 1.517(4) . ?
C10 C11 1.520(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.517(4) . ?
C14 C16 1.521(4) . ?
C14 C17 1.520(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C4 N1 O1 104.25(18) . . ?
C4 N1 C1 106.10(19) . . ?
O1 N1 C1 104.27(17) . . ?
C3 O1 N1 103.89(17) . . ?
C9 O2 H2 109.5 . . ?
C5 O3 C14 116.97(19) . . ?
C6 O4 C10 117.5(2) . . ?
N1 C1 C2 105.94(19) . . ?
N1 C1 C6 106.7(2) . . ?
C2 C1 C6 115.9(2) . . ?
N1 C1 H1 109.4 . . ?
C2 C1 H1 109.4 . . ?
C6 C1 H1 109.4 . . ?
C3 C2 C9 115.7(2) . . ?
C3 C2 C1 102.2(2) . . ?
C9 C2 C1 112.2(2) . . ?
C3 C2 H2A 108.8 . . ?
C9 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
O1 C3 C7 114.1(2) . . ?
O1 C3 C8 117.5(2) . . ?
C7 C3 C8 61.11(18) . . ?
O1 C3 C2 105.62(19) . . ?
C7 C3 C2 127.7(2) . . ?
C8 C3 C2 125.8(2) . . ?
N1 C4 C5 107.3(2) . . ?
N1 C4 H4A 110.2 . . ?
C5 C4 H4A 110.2 . . ?
N1 C4 H4B 110.2 . . ?
C5 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
O3 C5 C4 110.8(2) . . ?
O3 C5 C6 110.6(2) . . ?
C4 C5 C6 101.45(19) . . ?
O3 C5 H5 111.2 . . ?
C4 C5 H5 111.2 . . ?
C6 C5 H5 111.2 . . ?
O4 C6 C5 106.4(2) . . ?
O4 C6 C1 111.85(19) . . ?
C5 C6 C1 103.8(2) . . ?
O4 C6 H6 111.5 . . ?
C5 C6 H6 111.5 . . ?
C1 C6 H6 111.5 . . ?
C3 C7 C8 60.00(17) . . ?
C3 C7 H7A 117.8 . . ?
C8 C7 H7A 117.8 . . ?
C3 C7 H7B 117.8 . . ?
C8 C7 H7B 117.8 . . ?
H7A C7 H7B 114.9 . . ?
C3 C8 C7 58.89(17) . . ?
C3 C8 H8A 117.9 . . ?
C7 C8 H8A 117.9 . . ?
C3 C8 H8B 117.9 . . ?
C7 C8 H8B 117.9 . . ?
H8A C8 H8B 115.0 . . ?
O2 C9 C2 113.1(2) . . ?
O2 C9 H9A 109.0 . . ?
C2 C9 H9A 109.0 . . ?
O2 C9 H9B 109.0 . . ?
C2 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
O4 C10 C12 102.9(2) . . ?
O4 C10 C13 110.5(2) . . ?
C12 C10 C13 110.5(3) . . ?
O4 C10 C11 110.4(2) . . ?
C12 C10 C11 111.1(2) . . ?
C13 C10 C11 111.2(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 C15 103.4(2) . . ?
O3 C14 C16 110.0(2) . . ?
C15 C14 C16 110.4(2) . . ?
O3 C14 C17 110.8(2) . . ?
C15 C14 C17 110.5(2) . . ?
C16 C14 C17 111.4(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 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.042

_shelxl_version_number           2014/6



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1121
_database_code_depnum_ccdc_archive 'CCDC 1496577'
_audit_update_record             
;
2016-07-28 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;
#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             
;
'Wed Feb 12 17:01:31 2014'
;
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
(3aS,6R,7S,7aR)-7-(tert-butoxy)tetrahydro-3aH-spiro
[1,6-methanopyrano[4,3-c]isoxazole-3,1'-cyclopropane]
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C13 H21 N O3)'
_chemical_formula_sum            'C52 H84 N4 O12'
_chemical_formula_weight         957.23
_chemical_absolute_configuration syn

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.178(1)
_cell_length_b                   21.780(1)
_cell_length_c                   11.615(1)
_cell_angle_alpha                90
_cell_angle_beta                 90.547(1)
_cell_angle_gamma                90
_cell_volume                     2574.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8140
_cell_measurement_theta_min      4.3104
_cell_measurement_theta_max      70.2713

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9485
_exptl_absorpt_correction_T_max  0.9791
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.41 (release 13-09-2010 CrysAlis171 .NET)
(compiled Sep 13 2010,14:28:38)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1241
_diffrn_reflns_number            14484
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.314
_diffrn_reflns_theta_max         70.399
_diffrn_reflns_theta_full        68.689
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measured_fraction_theta_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_Laue_measured_fraction_full 0.954
_reflns_number_total             7357
_reflns_number_gt                6479
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.594
_reflns_Friedel_fraction_max     0.573
_reflns_Friedel_fraction_full    0.602
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -24.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       46.2824  -37.0000 -150.0000 90

#__ type_ start__ end____ width___ exp.time_
  2 omega   74.00  117.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       46.2824  125.0000  -60.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega  -51.00  -25.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   45.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -75.00  -36.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   45.0000  150.0000 39

#__ type_ start__ end____ width___ exp.time_
  5 omega   36.00  120.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -77.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  6 omega   80.00  165.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919   45.0000 -120.0000 85

#__ type_ start__ end____ width___ exp.time_
  7 omega   77.00  166.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  125.0000  -90.0000 89

#__ type_ start__ end____ width___ exp.time_
  8 omega   28.00   75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -45.0000 -120.0000 47

#__ type_ start__ end____ width___ exp.time_
  9 omega -118.00  -16.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -46.2824  -77.0000  -30.0000 102

#__ type_ start__ end____ width___ exp.time_
 10 omega -118.00  -16.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -46.2824  -77.0000 -180.0000 102

#__ type_ start__ end____ width___ exp.time_
 11 omega -167.00 -133.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -15.0000   60.0000 34

#__ type_ start__ end____ width___ exp.time_
 12 omega   28.00   77.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -45.0000  -60.0000 49

;

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.41 (release 13-09-2010 CrysAlis171 .NET)
(compiled Sep 13 2010,14:28:38)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.41 (release 13-09-2010 CrysAlis171 .NET)
(compiled Sep 13 2010,14:28:38)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.41 (release 13-09-2010 CrysAlis171 .NET)
(compiled Sep 13 2010,14:28:38)
;
_computing_structure_solution    'SIR2004 J.Appl.Cryst.38,381-388'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0618P)²+0.4474P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 x determined using 2250 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(12)
_refine_ls_number_reflns         7357
_refine_ls_number_parameters     613
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1170
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 0.2573(3) 0.91091(16) 0.3962(3) 0.0321(8) Uani 1 1 d . . . . .
O1A O 0.2572(3) 0.84889(14) 0.4384(3) 0.0391(7) Uani 1 1 d . . . . .
O2A O 0.0392(3) 0.89214(13) 0.2066(2) 0.0300(6) Uani 1 1 d . . . . .
O3A O 0.1899(3) 1.02950(13) 0.3395(3) 0.0433(8) Uani 1 1 d . . . . .
C1A C 0.1247(4) 0.9349(2) 0.4254(3) 0.0297(9) Uani 1 1 d . . . . .
H1A H 0.1232 0.9540 0.5018 0.036 Uiso 1 1 calc R U . . .
C2A C 0.0976(4) 0.98046(18) 0.3305(4) 0.0297(9) Uani 1 1 d . . . . .
H2A H 0.0062 0.9946 0.3285 0.036 Uiso 1 1 calc R U . . .
C3A C 0.1331(4) 0.94056(19) 0.2269(3) 0.0296(9) Uani 1 1 d . . . . .
H3A H 0.1452 0.9656 0.1577 0.035 Uiso 1 1 calc R U . . .
C4A C 0.2626(4) 0.9125(2) 0.2673(4) 0.0352(10) Uani 1 1 d . . . . .
H4A1 H 0.2726 0.8714 0.2366 0.042 Uiso 1 1 calc R U . . .
H4A2 H 0.3361 0.9373 0.2420 0.042 Uiso 1 1 calc R U . . .
C5A C 0.0317(4) 0.87903(18) 0.4169(3) 0.0261(8) Uani 1 1 d . . . . .
H5A H -0.0304 0.8798 0.4809 0.031 Uiso 1 1 calc R U . . .
C6A C 0.1262(4) 0.82502(19) 0.4320(3) 0.0281(9) Uani 1 1 d . . . . .
C7A C 0.1059(4) 0.7719(2) 0.5090(4) 0.0388(10) Uani 1 1 d . . . . .
H7A1 H 0.0212 0.7678 0.5458 0.047 Uiso 1 1 calc R U . . .
H7A2 H 0.1802 0.7577 0.5547 0.047 Uiso 1 1 calc R U . . .
C8A C 0.1115(5) 0.7635(2) 0.3802(4) 0.0445(11) Uani 1 1 d . . . . .
H8A1 H 0.1891 0.7442 0.3485 0.053 Uiso 1 1 calc R U . . .
H8A2 H 0.0301 0.7543 0.3396 0.053 Uiso 1 1 calc R U . . .
C9A C -0.0434(4) 0.88005(19) 0.3029(3) 0.0272(8) Uani 1 1 d . . . . .
H9A1 H -0.0865 0.8407 0.2917 0.033 Uiso 1 1 calc R U . . .
H9A2 H -0.1111 0.9113 0.3063 0.033 Uiso 1 1 calc R U . . .
C10A C 0.1470(4) 1.09132(18) 0.3147(4) 0.0289(9) Uani 1 1 d . . . . .
C11A C 0.0750(5) 1.1161(2) 0.4184(4) 0.0453(12) Uani 1 1 d . . . . .
H11A H 0.0460 1.1573 0.4028 0.068 Uiso 1 1 calc R U . . .
H11B H 0.0004 1.0906 0.4340 0.068 Uiso 1 1 calc R U . . .
H11C H 0.1331 1.1163 0.4840 0.068 Uiso 1 1 calc R U . . .
C12A C 0.0610(6) 1.0943(3) 0.2072(5) 0.0649(17) Uani 1 1 d . . . . .
H12A H 0.0345 1.1360 0.1937 0.097 Uiso 1 1 calc R U . . .
H12B H 0.1096 1.0796 0.1423 0.097 Uiso 1 1 calc R U . . .
H12C H -0.0155 1.0692 0.2176 0.097 Uiso 1 1 calc R U . . .
C13A C 0.2738(4) 1.1268(2) 0.2975(5) 0.0483(12) Uani 1 1 d . . . . .
H13A H 0.2537 1.1689 0.2804 0.072 Uiso 1 1 calc R U . . .
H13B H 0.3263 1.1247 0.3664 0.072 Uiso 1 1 calc R U . . .
H13C H 0.3215 1.1092 0.2347 0.072 Uiso 1 1 calc R U . . .
N1B N 0.7770(3) 0.97577(15) 0.4803(3) 0.0274(7) Uani 1 1 d . . . . .
O1B O 0.7922(3) 1.04027(13) 0.4500(3) 0.0358(7) Uani 1 1 d . . . . .
O2B O 0.5301(3) 0.99183(14) 0.6416(2) 0.0328(7) Uani 1 1 d . . . . .
O3B O 0.6829(2) 0.85731(13) 0.5040(3) 0.0334(6) Uani 1 1 d . . . . .
C1B C 0.6472(3) 0.95955(17) 0.4287(3) 0.0236(8) Uani 1 1 d . . . . .
H1B H 0.6542 0.9452 0.3490 0.028 Uiso 1 1 calc R U . . .
C2B C 0.5990(4) 0.90983(17) 0.5097(3) 0.0260(8) Uani 1 1 d . . . . .
H2B H 0.5063 0.8995 0.4968 0.031 Uiso 1 1 calc R U . . .
C3B C 0.6227(4) 0.9426(2) 0.6245(3) 0.0304(9) Uani 1 1 d . . . . .
H3B H 0.6214 0.9135 0.6889 0.036 Uiso 1 1 calc R U . . .
C4B C 0.7609(4) 0.9686(2) 0.6066(3) 0.0315(9) Uani 1 1 d . . . . .
H4B1 H 0.7701 1.0079 0.6450 0.038 Uiso 1 1 calc R U . . .
H4B2 H 0.8267 0.9407 0.6375 0.038 Uiso 1 1 calc R U . . .
C5B C 0.5626(4) 1.01837(17) 0.4392(3) 0.0247(8) Uani 1 1 d . . . . .
H5B H 0.5149 1.0258 0.3668 0.030 Uiso 1 1 calc R U . . .
C6B C 0.6663(4) 1.06803(18) 0.4575(3) 0.0282(9) Uani 1 1 d . . . . .
C7B C 0.6606(5) 1.13177(19) 0.4099(4) 0.0397(10) Uani 1 1 d . . . . .
H7B1 H 0.5807 1.1443 0.3703 0.048 Uiso 1 1 calc R U . . .
H7B2 H 0.7408 1.1491 0.3792 0.048 Uiso 1 1 calc R U . . .
C8B C 0.6541(5) 1.1212(2) 0.5391(4) 0.0425(11) Uani 1 1 d . . . . .
H8B1 H 0.7304 1.1321 0.5853 0.051 Uiso 1 1 calc R U . . .
H8B2 H 0.5703 1.1274 0.5764 0.051 Uiso 1 1 calc R U . . .
C9B C 0.4658(4) 1.01202(19) 0.5374(3) 0.0284(9) Uani 1 1 d . . . . .
H9B1 H 0.4237 1.0513 0.5509 0.034 Uiso 1 1 calc R U . . .
H9B2 H 0.3981 0.9827 0.5160 0.034 Uiso 1 1 calc R U . . .
C10B C 0.6232(4) 0.79956(18) 0.4717(4) 0.0298(9) Uani 1 1 d . . . . .
C11B C 0.5635(4) 0.8037(2) 0.3523(4) 0.0431(11) Uani 1 1 d . . . . .
H11D H 0.5243 0.7650 0.3322 0.065 Uiso 1 1 calc R U . . .
H11E H 0.4974 0.8352 0.3509 0.065 Uiso 1 1 calc R U . . .
H11F H 0.6307 0.8135 0.2980 0.065 Uiso 1 1 calc R U . . .
C12B C 0.5222(4) 0.7809(2) 0.5613(4) 0.0414(11) Uani 1 1 d . . . . .
H12D H 0.4830 0.7425 0.5394 0.062 Uiso 1 1 calc R U . . .
H12E H 0.5647 0.7766 0.6349 0.062 Uiso 1 1 calc R U . . .
H12F H 0.4554 0.8119 0.5658 0.062 Uiso 1 1 calc R U . . .
C13B C 0.7388(4) 0.7554(2) 0.4734(4) 0.0405(11) Uani 1 1 d . . . . .
H13D H 0.7089 0.7150 0.4528 0.061 Uiso 1 1 calc R U . . .
H13E H 0.8034 0.7688 0.4193 0.061 Uiso 1 1 calc R U . . .
H13F H 0.7771 0.7544 0.5493 0.061 Uiso 1 1 calc R U . . .
N1C N 0.0445(3) 1.07321(16) 0.8594(3) 0.0295(7) Uani 1 1 d . . . . .
O1C O 0.0348(2) 1.13098(13) 0.9197(2) 0.0322(6) Uani 1 1 d . . . . .
O2C O 0.2803(3) 1.10842(13) 0.6959(2) 0.0305(6) Uani 1 1 d . . . . .
O3C O 0.1316(3) 0.96125(13) 0.7690(2) 0.0324(6) Uani 1 1 d . . . . .
C1C C 0.1765(4) 1.04987(18) 0.8938(4) 0.0275(9) Uani 1 1 d . . . . .
H1C H 0.1739 1.0255 0.9647 0.033 Uiso 1 1 calc R U . . .
C2C C 0.2166(4) 1.01167(18) 0.7898(3) 0.0287(9) Uani 1 1 d . . . . .
H2C H 0.3094 0.9997 0.7925 0.034 Uiso 1 1 calc R U . . .
C3C C 0.1874(4) 1.05869(19) 0.6965(3) 0.0290(9) Uani 1 1 d . . . . .
H3C H 0.1826 1.0390 0.6208 0.035 Uiso 1 1 calc R U . . .
C4C C 0.0523(4) 1.0822(2) 0.7320(3) 0.0300(9) Uani 1 1 d . . . . .
H1C1 H 0.0428 1.1253 0.7127 0.036 Uiso 1 1 calc R U . . .
H1C2 H -0.0166 1.0593 0.6930 0.036 Uiso 1 1 calc R U . . .
C5C C 0.2638(4) 1.10806(18) 0.9069(3) 0.0270(8) Uani 1 1 d . . . . .
H5C H 0.3177 1.1050 0.9771 0.032 Uiso 1 1 calc R U . . .
C6C C 0.1625(4) 1.15854(18) 0.9203(3) 0.0264(8) Uani 1 1 d . . . . .
C7C C 0.1721(4) 1.22130(19) 0.8693(4) 0.0363(10) Uani 1 1 d . . . . .
H7C1 H 0.0936 1.2387 0.8342 0.044 Uiso 1 1 calc R U . . .
H7C2 H 0.2538 1.2326 0.8327 0.044 Uiso 1 1 calc R U . . .
C8C C 0.1736(4) 1.21265(19) 0.9980(4) 0.0354(10) Uani 1 1 d . . . . .
H8C1 H 0.2563 1.2189 1.0386 0.042 Uiso 1 1 calc R U . . .
H8C2 H 0.0961 1.2249 1.0402 0.042 Uiso 1 1 calc R U . . .
C9C C 0.3521(4) 1.1149(2) 0.8024(3) 0.0314(9) Uani 1 1 d . . . . .
H9C1 H 0.3937 1.1550 0.8045 0.038 Uiso 1 1 calc R U . . .
H9C2 H 0.4207 1.0841 0.8059 0.038 Uiso 1 1 calc R U . . .
C10C C 0.1739(4) 0.90062(18) 0.8051(3) 0.0282(9) Uani 1 1 d . . . . .
C11C C 0.2011(4) 0.8978(2) 0.9337(3) 0.0339(9) Uani 1 1 d . . . . .
H11G H 0.2288 0.8570 0.9543 0.051 Uiso 1 1 calc R U . . .
H11H H 0.2692 0.9265 0.9534 0.051 Uiso 1 1 calc R U . . .
H11I H 0.1226 0.9079 0.9746 0.051 Uiso 1 1 calc R U . . .
C12C C 0.2933(4) 0.8803(2) 0.7372(4) 0.0341(9) Uani 1 1 d . . . . .
H12G H 0.3200 0.8401 0.7622 0.051 Uiso 1 1 calc R U . . .
H12H H 0.2714 0.8791 0.6567 0.051 Uiso 1 1 calc R U . . .
H12I H 0.3640 0.9088 0.7499 0.051 Uiso 1 1 calc R U . . .
C13C C 0.0564(4) 0.8611(2) 0.7740(4) 0.0391(10) Uani 1 1 d . . . . .
H13G H 0.0741 0.8192 0.7947 0.059 Uiso 1 1 calc R U . . .
H13H H -0.0192 0.8754 0.8150 0.059 Uiso 1 1 calc R U . . .
H13I H 0.0397 0.8637 0.6927 0.059 Uiso 1 1 calc R U . . .
N1D N 0.5338(3) 1.00679(16) 0.9759(3) 0.0293(7) Uani 1 1 d . . . . .
O1D O 0.5272(3) 0.94321(13) 0.9419(2) 0.0334(6) Uani 1 1 d . . . . .
O2D O 0.7878(3) 0.99634(13) 1.1382(2) 0.0316(6) Uani 1 1 d . . . . .
O3D O 0.6158(3) 1.12776(13) 1.0084(3) 0.0358(7) Uani 1 1 d . . . . .
C1D C 0.6600(3) 1.02849(18) 0.9267(3) 0.0252(8) Uani 1 1 d . . . . .
H1D H 0.6498 1.0439 0.8479 0.030 Uiso 1 1 calc R U . . .
C2D C 0.7047(4) 1.07745(18) 1.0096(3) 0.0279(9) Uani 1 1 d . . . . .
H2D H 0.7959 1.0901 0.9972 0.033 Uiso 1 1 calc R U . . .
C3D C 0.6871(4) 1.04154(19) 1.1227(3) 0.0297(9) Uani 1 1 d . . . . .
H3D H 0.6853 1.0697 1.1885 0.036 Uiso 1 1 calc R U . . .
C4D C 0.5530(4) 1.0127(2) 1.1034(3) 0.0349(10) Uani 1 1 d . . . . .
H4D1 H 0.5492 0.9726 1.1397 0.042 Uiso 1 1 calc R U . . .
H4D2 H 0.4850 1.0384 1.1359 0.042 Uiso 1 1 calc R U . . .
C5D C 0.7532(3) 0.97153(17) 0.9341(3) 0.0238(8) Uani 1 1 d . . . . .
H5D H 0.8002 0.9665 0.8614 0.029 Uiso 1 1 calc R U . . .
C6D C 0.6577(4) 0.91885(19) 0.9504(3) 0.0278(9) Uani 1 1 d . . . . .
C7D C 0.6779(5) 0.8658(2) 1.0313(4) 0.0403(11) Uani 1 1 d . . . . .
H7D1 H 0.6037 0.8526 1.0769 0.048 Uiso 1 1 calc R U . . .
H7D2 H 0.7629 0.8618 1.0689 0.048 Uiso 1 1 calc R U . . .
C8D C 0.6708(4) 0.8557(2) 0.9028(4) 0.0395(10) Uani 1 1 d . . . . .
H8D1 H 0.7515 0.8455 0.8635 0.047 Uiso 1 1 calc R U . . .
H8D2 H 0.5924 0.8363 0.8715 0.047 Uiso 1 1 calc R U . . .
C9D C 0.8508(4) 0.97904(19) 1.0328(3) 0.0269(8) Uani 1 1 d . . . . .
H9D1 H 0.8974 0.9407 1.0444 0.032 Uiso 1 1 calc R U . . .
H9D2 H 0.9147 1.0102 1.0126 0.032 Uiso 1 1 calc R U . . .
C10D C 0.6707(4) 1.1887(2) 0.9975(4) 0.0347(10) Uani 1 1 d . . . . .
C11D C 0.7270(5) 1.1972(3) 0.8786(4) 0.0506(13) Uani 1 1 d . . . . .
H11J H 0.7633 1.2377 0.8721 0.076 Uiso 1 1 calc R U . . .
H11K H 0.7949 1.1673 0.8662 0.076 Uiso 1 1 calc R U . . .
H11L H 0.6587 1.1919 0.8219 0.076 Uiso 1 1 calc R U . . .
C12D C 0.7743(5) 1.2009(2) 1.0895(5) 0.0485(12) Uani 1 1 d . . . . .
H12J H 0.8089 1.2416 1.0801 0.073 Uiso 1 1 calc R U . . .
H12K H 0.7355 1.1973 1.1643 0.073 Uiso 1 1 calc R U . . .
H12L H 0.8441 1.1715 1.0825 0.073 Uiso 1 1 calc R U . . .
C13D C 0.5535(4) 1.2308(2) 1.0141(5) 0.0459(12) Uani 1 1 d . . . . .
H13J H 0.5814 1.2728 1.0082 0.069 Uiso 1 1 calc R U . . .
H13K H 0.4884 1.2224 0.9559 0.069 Uiso 1 1 calc R U . . .
H13L H 0.5167 1.2239 1.0888 0.069 Uiso 1 1 calc R U . . .


_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
N1A O1A 1.437(5) . ?
N1A C1A 1.489(5) . ?
N1A C4A 1.500(5) . ?
O1A C6A 1.432(5) . ?
O2A C9A 1.431(4) . ?
O2A C3A 1.441(5) . ?
O3A C2A 1.426(5) . ?
O3A C10A 1.444(5) . ?
C1A C2A 1.508(6) . ?
C1A C5A 1.544(6) . ?
C1A H1A 0.9800 . ?
C2A C3A 1.530(5) . ?
C2A H2A 0.9800 . ?
C3A C4A 1.523(6) . ?
C3A H3A 0.9800 . ?
C4A H4A1 0.9700 . ?
C4A H4A2 0.9700 . ?
C5A C9A 1.524(5) . ?
C5A C6A 1.529(5) . ?
C5A H5A 0.9800 . ?
C6A C8A 1.477(6) . ?
C6A C7A 1.479(6) . ?
C7A C8A 1.509(7) . ?
C7A H7A1 0.9700 . ?
C7A H7A2 0.9700 . ?
C8A H8A1 0.9700 . ?
C8A H8A2 0.9700 . ?
C9A H9A1 0.9700 . ?
C9A H9A2 0.9700 . ?
C10A C11A 1.515(6) . ?
C10A C12A 1.520(7) . ?
C10A C13A 1.519(6) . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
N1B O1B 1.457(4) . ?
N1B C4B 1.486(5) . ?
N1B C1B 1.488(5) . ?
O1B C6B 1.420(5) . ?
O2B C9B 1.439(5) . ?
O2B C3B 1.444(5) . ?
O3B C2B 1.429(5) . ?
O3B C10B 1.445(5) . ?
C1B C2B 1.519(5) . ?
C1B C5B 1.549(5) . ?
C1B H1B 0.9800 . ?
C2B C3B 1.529(6) . ?
C2B H2B 0.9800 . ?
C3B C4B 1.532(5) . ?
C3B H3B 0.9800 . ?
C4B H4B1 0.9700 . ?
C4B H4B2 0.9700 . ?
C5B C9B 1.521(5) . ?
C5B C6B 1.525(5) . ?
C5B H5B 0.9800 . ?
C6B C7B 1.495(6) . ?
C6B C8B 1.502(6) . ?
C7B C8B 1.520(6) . ?
C7B H7B1 0.9700 . ?
C7B H7B2 0.9700 . ?
C8B H8B1 0.9700 . ?
C8B H8B2 0.9700 . ?
C9B H9B1 0.9700 . ?
C9B H9B2 0.9700 . ?
C10B C11B 1.512(6) . ?
C10B C13B 1.520(6) . ?
C10B C12B 1.524(5) . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?
C13B H13D 0.9600 . ?
C13B H13E 0.9600 . ?
C13B H13F 0.9600 . ?
N1C O1C 1.444(4) . ?
N1C C1C 1.487(5) . ?
N1C C4C 1.495(5) . ?
O1C C6C 1.431(5) . ?
O2C C9C 1.437(5) . ?
O2C C3C 1.438(5) . ?
O3C C2C 1.417(5) . ?
O3C C10C 1.450(5) . ?
C1C C2C 1.526(5) . ?
C1C C5C 1.555(6) . ?
C1C H1C 0.9800 . ?
C2C C3C 1.518(6) . ?
C2C H2C 0.9800 . ?
C3C C4C 1.527(5) . ?
C3C H3C 0.9800 . ?
C4C H1C1 0.9700 . ?
C4C H1C2 0.9700 . ?
C5C C6C 1.516(5) . ?
C5C C9C 1.524(5) . ?
C5C H5C 0.9800 . ?
C6C C8C 1.488(6) . ?
C6C C7C 1.493(6) . ?
C7C C8C 1.506(6) . ?
C7C H7C1 0.9700 . ?
C7C H7C2 0.9700 . ?
C8C H8C1 0.9700 . ?
C8C H8C2 0.9700 . ?
C9C H9C1 0.9700 . ?
C9C H9C2 0.9700 . ?
C10C C13C 1.514(6) . ?
C10C C11C 1.517(6) . ?
C10C C12C 1.521(5) . ?
C11C H11G 0.9600 . ?
C11C H11H 0.9600 . ?
C11C H11I 0.9600 . ?
C12C H12G 0.9600 . ?
C12C H12H 0.9600 . ?
C12C H12I 0.9600 . ?
C13C H13G 0.9600 . ?
C13C H13H 0.9600 . ?
C13C H13I 0.9600 . ?
N1D O1D 1.442(4) . ?
N1D C1D 1.488(5) . ?
N1D C4D 1.497(5) . ?
O1D C6D 1.433(5) . ?
O2D C3D 1.431(5) . ?
O2D C9D 1.437(4) . ?
O3D C2D 1.421(5) . ?
O3D C10D 1.446(5) . ?
C1D C2D 1.504(6) . ?
C1D C5D 1.563(5) . ?
C1D H1D 0.9800 . ?
C2D C3D 1.540(5) . ?
C2D H2D 0.9800 . ?
C3D C4D 1.517(6) . ?
C3D H3D 0.9800 . ?
C4D H4D1 0.9700 . ?
C4D H4D2 0.9700 . ?
C5D C6D 1.517(5) . ?
C5D C9D 1.518(5) . ?
C5D H5D 0.9800 . ?
C6D C8D 1.489(6) . ?
C6D C7D 1.502(6) . ?
C7D C8D 1.509(6) . ?
C7D H7D1 0.9700 . ?
C7D H7D2 0.9700 . ?
C8D H8D1 0.9700 . ?
C8D H8D2 0.9700 . ?
C9D H9D1 0.9700 . ?
C9D H9D2 0.9700 . ?
C10D C11D 1.512(6) . ?
C10D C12D 1.518(7) . ?
C10D C13D 1.519(6) . ?
C11D H11J 0.9600 . ?
C11D H11K 0.9600 . ?
C11D H11L 0.9600 . ?
C12D H12J 0.9600 . ?
C12D H12K 0.9600 . ?
C12D H12L 0.9600 . ?
C13D H13J 0.9600 . ?
C13D H13K 0.9600 . ?
C13D H13L 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
O1A N1A C1A 104.3(3) . . ?
O1A N1A C4A 111.3(3) . . ?
C1A N1A C4A 105.1(3) . . ?
C6A O1A N1A 109.1(3) . . ?
C9A O2A C3A 113.6(3) . . ?
C2A O3A C10A 119.1(3) . . ?
N1A C1A C2A 103.0(3) . . ?
N1A C1A C5A 105.4(3) . . ?
C2A C1A C5A 111.4(3) . . ?
N1A C1A H1A 112.2 . . ?
C2A C1A H1A 112.2 . . ?
C5A C1A H1A 112.2 . . ?
O3A C2A C1A 108.9(3) . . ?
O3A C2A C3A 108.8(3) . . ?
C1A C2A C3A 99.1(3) . . ?
O3A C2A H2A 113.0 . . ?
C1A C2A H2A 113.0 . . ?
C3A C2A H2A 113.0 . . ?
O2A C3A C4A 109.1(3) . . ?
O2A C3A C2A 112.5(3) . . ?
C4A C3A C2A 101.3(3) . . ?
O2A C3A H3A 111.2 . . ?
C4A C3A H3A 111.2 . . ?
C2A C3A H3A 111.2 . . ?
N1A C4A C3A 106.1(3) . . ?
N1A C4A H4A1 110.5 . . ?
C3A C4A H4A1 110.5 . . ?
N1A C4A H4A2 110.5 . . ?
C3A C4A H4A2 110.5 . . ?
H4A1 C4A H4A2 108.7 . . ?
C9A C5A C6A 114.9(3) . . ?
C9A C5A C1A 110.3(3) . . ?
C6A C5A C1A 102.3(3) . . ?
C9A C5A H5A 109.7 . . ?
C6A C5A H5A 109.7 . . ?
C1A C5A H5A 109.7 . . ?
O1A C6A C8A 116.2(3) . . ?
O1A C6A C7A 112.8(3) . . ?
C8A C6A C7A 61.4(3) . . ?
O1A C6A C5A 108.1(3) . . ?
C8A C6A C5A 126.2(4) . . ?
C7A C6A C5A 125.5(3) . . ?
C6A C7A C8A 59.2(3) . . ?
C6A C7A H7A1 117.9 . . ?
C8A C7A H7A1 117.9 . . ?
C6A C7A H7A2 117.9 . . ?
C8A C7A H7A2 117.9 . . ?
H7A1 C7A H7A2 115.0 . . ?
C6A C8A C7A 59.4(3) . . ?
C6A C8A H8A1 117.8 . . ?
C7A C8A H8A1 117.8 . . ?
C6A C8A H8A2 117.8 . . ?
C7A C8A H8A2 117.8 . . ?
H8A1 C8A H8A2 115.0 . . ?
O2A C9A C5A 112.9(3) . . ?
O2A C9A H9A1 109.0 . . ?
C5A C9A H9A1 109.0 . . ?
O2A C9A H9A2 109.0 . . ?
C5A C9A H9A2 109.0 . . ?
H9A1 C9A H9A2 107.8 . . ?
O3A C10A C11A 108.8(4) . . ?
O3A C10A C12A 112.0(4) . . ?
C11A C10A C12A 111.0(4) . . ?
O3A C10A C13A 104.1(3) . . ?
C11A C10A C13A 109.9(4) . . ?
C12A C10A C13A 110.7(4) . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C10A C12A H12A 109.5 . . ?
C10A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C10A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C10A C13A H13A 109.5 . . ?
C10A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C10A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
O1B N1B C4B 110.7(3) . . ?
O1B N1B C1B 103.2(3) . . ?
C4B N1B C1B 105.5(3) . . ?
C6B O1B N1B 107.3(3) . . ?
C9B O2B C3B 113.8(3) . . ?
C2B O3B C10B 117.3(3) . . ?
N1B C1B C2B 102.1(3) . . ?
N1B C1B C5B 105.3(3) . . ?
C2B C1B C5B 110.9(3) . . ?
N1B C1B H1B 112.6 . . ?
C2B C1B H1B 112.6 . . ?
C5B C1B H1B 112.6 . . ?
O3B C2B C1B 110.2(3) . . ?
O3B C2B C3B 108.9(3) . . ?
C1B C2B C3B 99.1(3) . . ?
O3B C2B H2B 112.6 . . ?
C1B C2B H2B 112.6 . . ?
C3B C2B H2B 112.6 . . ?
O2B C3B C2B 111.6(3) . . ?
O2B C3B C4B 110.2(3) . . ?
C2B C3B C4B 101.1(3) . . ?
O2B C3B H3B 111.2 . . ?
C2B C3B H3B 111.2 . . ?
C4B C3B H3B 111.2 . . ?
N1B C4B C3B 106.4(3) . . ?
N1B C4B H4B1 110.4 . . ?
C3B C4B H4B1 110.4 . . ?
N1B C4B H4B2 110.4 . . ?
C3B C4B H4B2 110.4 . . ?
H4B1 C4B H4B2 108.6 . . ?
C9B C5B C6B 114.4(3) . . ?
C9B C5B C1B 110.4(3) . . ?
C6B C5B C1B 102.3(3) . . ?
C9B C5B H5B 109.8 . . ?
C6B C5B H5B 109.8 . . ?
C1B C5B H5B 109.8 . . ?
O1B C6B C7B 113.9(3) . . ?
O1B C6B C8B 116.6(3) . . ?
C7B C6B C8B 60.9(3) . . ?
O1B C6B C5B 108.3(3) . . ?
C7B C6B C5B 125.6(4) . . ?
C8B C6B C5B 125.0(3) . . ?
C6B C7B C8B 59.8(3) . . ?
C6B C7B H7B1 117.8 . . ?
C8B C7B H7B1 117.8 . . ?
C6B C7B H7B2 117.8 . . ?
C8B C7B H7B2 117.8 . . ?
H7B1 C7B H7B2 114.9 . . ?
C6B C8B C7B 59.3(3) . . ?
C6B C8B H8B1 117.8 . . ?
C7B C8B H8B1 117.8 . . ?
C6B C8B H8B2 117.8 . . ?
C7B C8B H8B2 117.8 . . ?
H8B1 C8B H8B2 115.0 . . ?
O2B C9B C5B 111.5(3) . . ?
O2B C9B H9B1 109.3 . . ?
C5B C9B H9B1 109.3 . . ?
O2B C9B H9B2 109.3 . . ?
C5B C9B H9B2 109.3 . . ?
H9B1 C9B H9B2 108.0 . . ?
O3B C10B C11B 110.5(3) . . ?
O3B C10B C13B 103.0(3) . . ?
C11B C10B C13B 110.8(4) . . ?
O3B C10B C12B 109.9(3) . . ?
C11B C10B C12B 111.9(4) . . ?
C13B C10B C12B 110.4(3) . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C10B C12B H12D 109.5 . . ?
C10B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C10B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C10B C13B H13D 109.5 . . ?
C10B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C10B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
O1C N1C C1C 103.5(3) . . ?
O1C N1C C4C 111.8(3) . . ?
C1C N1C C4C 104.7(3) . . ?
C6C O1C N1C 107.5(3) . . ?
C9C O2C C3C 113.5(3) . . ?
C2C O3C C10C 118.5(3) . . ?
N1C C1C C2C 102.8(3) . . ?
N1C C1C C5C 105.2(3) . . ?
C2C C1C C5C 111.4(3) . . ?
N1C C1C H1C 112.3 . . ?
C2C C1C H1C 112.3 . . ?
C5C C1C H1C 112.3 . . ?
O3C C2C C3C 106.7(3) . . ?
O3C C2C C1C 112.9(3) . . ?
C3C C2C C1C 98.3(3) . . ?
O3C C2C H2C 112.6 . . ?
C3C C2C H2C 112.6 . . ?
C1C C2C H2C 112.6 . . ?
O2C C3C C2C 112.8(3) . . ?
O2C C3C C4C 110.0(3) . . ?
C2C C3C C4C 101.8(3) . . ?
O2C C3C H3C 110.6 . . ?
C2C C3C H3C 110.6 . . ?
C4C C3C H3C 110.6 . . ?
N1C C4C C3C 106.3(3) . . ?
N1C C4C H1C1 110.5 . . ?
C3C C4C H1C1 110.5 . . ?
N1C C4C H1C2 110.5 . . ?
C3C C4C H1C2 110.5 . . ?
H1C1 C4C H1C2 108.7 . . ?
C6C C5C C9C 114.6(3) . . ?
C6C C5C C1C 102.3(3) . . ?
C9C C5C C1C 110.0(3) . . ?
C6C C5C H5C 109.9 . . ?
C9C C5C H5C 109.9 . . ?
C1C C5C H5C 109.9 . . ?
O1C C6C C8C 113.5(3) . . ?
O1C C6C C7C 116.4(3) . . ?
C8C C6C C7C 60.7(3) . . ?
O1C C6C C5C 108.3(3) . . ?
C8C C6C C5C 126.0(4) . . ?
C7C C6C C5C 125.2(3) . . ?
C6C C7C C8C 59.5(3) . . ?
C6C C7C H7C1 117.8 . . ?
C8C C7C H7C1 117.8 . . ?
C6C C7C H7C2 117.8 . . ?
C8C C7C H7C2 117.8 . . ?
H7C1 C7C H7C2 115.0 . . ?
C6C C8C C7C 59.8(3) . . ?
C6C C8C H8C1 117.8 . . ?
C7C C8C H8C1 117.8 . . ?
C6C C8C H8C2 117.8 . . ?
C7C C8C H8C2 117.8 . . ?
H8C1 C8C H8C2 114.9 . . ?
O2C C9C C5C 112.2(3) . . ?
O2C C9C H9C1 109.2 . . ?
C5C C9C H9C1 109.2 . . ?
O2C C9C H9C2 109.2 . . ?
C5C C9C H9C2 109.2 . . ?
H9C1 C9C H9C2 107.9 . . ?
O3C C10C C13C 102.5(3) . . ?
O3C C10C C11C 111.9(3) . . ?
C13C C10C C11C 110.4(3) . . ?
O3C C10C C12C 110.6(3) . . ?
C13C C10C C12C 110.1(3) . . ?
C11C C10C C12C 111.0(3) . . ?
C10C C11C H11G 109.5 . . ?
C10C C11C H11H 109.5 . . ?
H11G C11C H11H 109.5 . . ?
C10C C11C H11I 109.5 . . ?
H11G C11C H11I 109.5 . . ?
H11H C11C H11I 109.5 . . ?
C10C C12C H12G 109.5 . . ?
C10C C12C H12H 109.5 . . ?
H12G C12C H12H 109.5 . . ?
C10C C12C H12I 109.5 . . ?
H12G C12C H12I 109.5 . . ?
H12H C12C H12I 109.5 . . ?
C10C C13C H13G 109.5 . . ?
C10C C13C H13H 109.5 . . ?
H13G C13C H13H 109.5 . . ?
C10C C13C H13I 109.5 . . ?
H13G C13C H13I 109.5 . . ?
H13H C13C H13I 109.5 . . ?
O1D N1D C1D 103.8(3) . . ?
O1D N1D C4D 111.0(3) . . ?
C1D N1D C4D 104.3(3) . . ?
C6D O1D N1D 107.2(3) . . ?
C3D O2D C9D 113.5(3) . . ?
C2D O3D C10D 117.5(3) . . ?
N1D C1D C2D 103.7(3) . . ?
N1D C1D C5D 104.6(3) . . ?
C2D C1D C5D 110.3(3) . . ?
N1D C1D H1D 112.5 . . ?
C2D C1D H1D 112.5 . . ?
C5D C1D H1D 112.5 . . ?
O3D C2D C1D 110.6(3) . . ?
O3D C2D C3D 108.7(3) . . ?
C1D C2D C3D 98.6(3) . . ?
O3D C2D H2D 112.7 . . ?
C1D C2D H2D 112.7 . . ?
C3D C2D H2D 112.7 . . ?
O2D C3D C4D 112.1(3) . . ?
O2D C3D C2D 111.5(3) . . ?
C4D C3D C2D 101.3(3) . . ?
O2D C3D H3D 110.5 . . ?
C4D C3D H3D 110.5 . . ?
C2D C3D H3D 110.5 . . ?
N1D C4D C3D 106.9(3) . . ?
N1D C4D H4D1 110.3 . . ?
C3D C4D H4D1 110.3 . . ?
N1D C4D H4D2 110.3 . . ?
C3D C4D H4D2 110.3 . . ?
H4D1 C4D H4D2 108.6 . . ?
C6D C5D C9D 113.8(3) . . ?
C6D C5D C1D 102.6(3) . . ?
C9D C5D C1D 110.4(3) . . ?
C6D C5D H5D 110.0 . . ?
C9D C5D H5D 110.0 . . ?
C1D C5D H5D 110.0 . . ?
O1D C6D C8D 113.7(3) . . ?
O1D C6D C7D 116.7(3) . . ?
C8D C6D C7D 60.6(3) . . ?
O1D C6D C5D 107.8(3) . . ?
C8D C6D C5D 126.4(3) . . ?
C7D C6D C5D 125.2(3) . . ?
C6D C7D C8D 59.3(3) . . ?
C6D C7D H7D1 117.8 . . ?
C8D C7D H7D1 117.8 . . ?
C6D C7D H7D2 117.8 . . ?
C8D C7D H7D2 117.8 . . ?
H7D1 C7D H7D2 115.0 . . ?
C6D C8D C7D 60.1(3) . . ?
C6D C8D H8D1 117.8 . . ?
C7D C8D H8D1 117.8 . . ?
C6D C8D H8D2 117.8 . . ?
C7D C8D H8D2 117.8 . . ?
H8D1 C8D H8D2 114.9 . . ?
O2D C9D C5D 112.2(3) . . ?
O2D C9D H9D1 109.2 . . ?
C5D C9D H9D1 109.2 . . ?
O2D C9D H9D2 109.2 . . ?
C5D C9D H9D2 109.2 . . ?
H9D1 C9D H9D2 107.9 . . ?
O3D C10D C11D 110.0(4) . . ?
O3D C10D C12D 111.4(4) . . ?
C11D C10D C12D 110.8(4) . . ?
O3D C10D C13D 103.8(3) . . ?
C11D C10D C13D 110.3(4) . . ?
C12D C10D C13D 110.3(4) . . ?
C10D C11D H11J 109.5 . . ?
C10D C11D H11K 109.5 . . ?
H11J C11D H11K 109.5 . . ?
C10D C11D H11L 109.5 . . ?
H11J C11D H11L 109.5 . . ?
H11K C11D H11L 109.5 . . ?
C10D C12D H12J 109.5 . . ?
C10D C12D H12K 109.5 . . ?
H12J C12D H12K 109.5 . . ?
C10D C12D H12L 109.5 . . ?
H12J C12D H12L 109.5 . . ?
H12K C12D H12L 109.5 . . ?
C10D C13D H13J 109.5 . . ?
C10D C13D H13K 109.5 . . ?
H13J C13D H13K 109.5 . . ?
C10D C13D H13L 109.5 . . ?
H13J C13D H13L 109.5 . . ?
H13K C13D H13L 109.5 . . ?

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.063

_shelxl_version_number           2014/6



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_24
_database_code_depnum_ccdc_archive 'CCDC 1496578'
_audit_update_record             
;
2016-07-28 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             
;
'Tue Sep 08 12:57:44 2015'
;
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic


_chemical_name_systematic        
;
(4aS,7R,8S,8aR)-8-(tert-butoxy)hexahydro-1,7-methanopyrano
[4,3-b]pyridin-4(7H)-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H21 N O3'
_chemical_formula_sum            'C13 H21 N O3'
_chemical_formula_weight         239.31
_chemical_absolute_configuration syn

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.0780(2)
_cell_length_b                   10.2040(3)
_cell_length_c                   19.9570(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1237.73(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2255
_cell_measurement_theta_min      6.1820
_cell_measurement_theta_max      70.2180

_exptl_crystal_description       prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9605
_exptl_absorpt_correction_T_max  0.9782
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1241
_diffrn_reflns_number            3991
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.867
_diffrn_reflns_theta_max         70.378
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.983
_reflns_number_total             1946
_reflns_number_gt                1675
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.441
_reflns_Friedel_fraction_max     0.614
_reflns_Friedel_fraction_full    0.651
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -75.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.2824   19.0000 -180.0000 105

#__ type_ start__ end____ width___ exp.time_
  2 omega   73.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       46.2824  125.0000 -150.0000 45

#__ type_ start__ end____ width___ exp.time_
  3 omega  -69.00  -17.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   30.0000  120.0000 52

#__ type_ start__ end____ width___ exp.time_
  4 omega   16.00  109.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -94.0000   90.0000 93

#__ type_ start__ end____ width___ exp.time_
  5 omega   28.00   74.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -45.0000 -120.0000 46

#__ type_ start__ end____ width___ exp.time_
  6 omega   39.00   66.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  7 omega   29.00   61.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -45.0000   90.0000 32

#__ type_ start__ end____ width___ exp.time_
  8 omega   25.00   58.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000 -150.0000 33

;

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_structure_solution    'SIR2004 J.Appl.Cryst.38,381-388'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0456P)²+0.0713P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 x determined using 475 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_number_reflns         1946
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7690(4) 0.8732(2) -0.02747(11) 0.0199(5) Uani 1 1 d . . . . .
O1 O 0.8156(4) 1.17688(19) -0.04332(9) 0.0248(5) Uani 1 1 d . . . . .
O2 O 0.3043(3) 0.9709(2) -0.17310(10) 0.0337(5) Uani 1 1 d . . . . .
O3 O 0.6822(3) 0.9738(2) 0.10250(9) 0.0229(5) Uani 1 1 d . . . . .
C1 C 0.5705(4) 0.9526(3) -0.01329(13) 0.0188(6) Uani 1 1 d . . . . .
H1 H 0.4484 0.8973 0.0019 0.023 Uiso 1 1 calc R U . . .
C2 C 0.6468(4) 1.0445(3) 0.04191(13) 0.0201(6) Uani 1 1 d . . . . .
H2 H 0.5454 1.1181 0.0482 0.024 Uiso 1 1 calc R U . . .
C3 C 0.8653(5) 1.0880(3) 0.01079(14) 0.0228(6) Uani 1 1 d . . . . .
H3 H 0.9606 1.1295 0.0442 0.027 Uiso 1 1 calc R U . . .
C4 C 0.9605(4) 0.9578(3) -0.01274(14) 0.0230(6) Uani 1 1 d . . . . .
H4A H 1.0496 0.9701 -0.0526 0.028 Uiso 1 1 calc R U . . .
H4B H 1.0513 0.9190 0.0220 0.028 Uiso 1 1 calc R U . . .
C5 C 0.7721(5) 0.8106(3) -0.09420(14) 0.0249(6) Uani 1 1 d . . . . .
H5A H 0.8264 0.7216 -0.0899 0.030 Uiso 1 1 calc R U . . .
H5B H 0.8725 0.8581 -0.1231 0.030 Uiso 1 1 calc R U . . .
C6 C 0.5438(5) 0.8077(3) -0.12660(15) 0.0284(7) Uani 1 1 d . . . . .
H6A H 0.5565 0.7722 -0.1715 0.034 Uiso 1 1 calc R U . . .
H6B H 0.4494 0.7497 -0.1010 0.034 Uiso 1 1 calc R U . . .
C7 C 0.4379(4) 0.9414(3) -0.13035(14) 0.0241(7) Uani 1 1 d . . . . .
C8 C 0.5048(4) 1.0343(3) -0.07486(13) 0.0203(6) Uani 1 1 d . . . . .
H8 H 0.3815 1.0920 -0.0635 0.024 Uiso 1 1 calc R U . . .
C9 C 0.7029(5) 1.1164(3) -0.09746(14) 0.0227(6) Uani 1 1 d . . . . .
H9A H 0.8048 1.0604 -0.1215 0.027 Uiso 1 1 calc R U . . .
H9B H 0.6526 1.1837 -0.1282 0.027 Uiso 1 1 calc R U . . .
C10 C 0.5991(5) 1.0336(3) 0.16371(14) 0.0228(6) Uani 1 1 d . . . . .
C11 C 0.6692(5) 0.9386(3) 0.21781(14) 0.0309(8) Uani 1 1 d . . . . .
H11A H 0.6208 0.9702 0.2606 0.046 Uiso 1 1 calc R U . . .
H11B H 0.6046 0.8543 0.2093 0.046 Uiso 1 1 calc R U . . .
H11C H 0.8266 0.9308 0.2178 0.046 Uiso 1 1 calc R U . . .
C12 C 0.7015(5) 1.1681(3) 0.17473(15) 0.0292(7) Uani 1 1 d . . . . .
H12A H 0.6445 1.2056 0.2153 0.044 Uiso 1 1 calc R U . . .
H12B H 0.8584 1.1594 0.1783 0.044 Uiso 1 1 calc R U . . .
H12C H 0.6664 1.2241 0.1376 0.044 Uiso 1 1 calc R U . . .
C13 C 0.3487(5) 1.0439(3) 0.16135(15) 0.0257(7) Uani 1 1 d . . . . .
H13A H 0.2964 1.0835 0.2020 0.039 Uiso 1 1 calc R U . . .
H13B H 0.3059 1.0968 0.1238 0.039 Uiso 1 1 calc R U . . .
H13C H 0.2864 0.9579 0.1568 0.039 Uiso 1 1 calc R U . . .


_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
N1 C5 1.477(3) . ?
N1 C4 1.478(4) . ?
N1 C1 1.480(3) . ?
O1 C9 1.420(3) . ?
O1 C3 1.442(3) . ?
O2 C7 1.216(3) . ?
O3 C2 1.424(3) . ?
O3 C10 1.456(3) . ?
C1 C2 1.519(4) . ?
C1 C8 1.538(4) . ?
C1 H1 0.9800 . ?
C2 C3 1.532(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.524(4) . ?
C3 H3 0.9800 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.531(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.510(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.513(4) . ?
C8 C9 1.534(4) . ?
C8 H8 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.513(4) . ?
C10 C12 1.523(4) . ?
C10 C13 1.526(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C5 N1 C4 114.9(2) . . ?
C5 N1 C1 114.8(2) . . ?
C4 N1 C1 106.5(2) . . ?
C9 O1 C3 113.4(2) . . ?
C2 O3 C10 116.60(19) . . ?
N1 C1 C2 103.2(2) . . ?
N1 C1 C8 110.8(2) . . ?
C2 C1 C8 108.9(2) . . ?
N1 C1 H1 111.2 . . ?
C2 C1 H1 111.2 . . ?
C8 C1 H1 111.2 . . ?
O3 C2 C1 110.5(2) . . ?
O3 C2 C3 111.1(2) . . ?
C1 C2 C3 98.6(2) . . ?
O3 C2 H2 112.0 . . ?
C1 C2 H2 112.0 . . ?
C3 C2 H2 112.0 . . ?
O1 C3 C4 113.4(2) . . ?
O1 C3 C2 107.7(2) . . ?
C4 C3 C2 101.6(2) . . ?
O1 C3 H3 111.2 . . ?
C4 C3 H3 111.2 . . ?
C2 C3 H3 111.2 . . ?
N1 C4 C3 105.7(2) . . ?
N1 C4 H4A 110.6 . . ?
C3 C4 H4A 110.6 . . ?
N1 C4 H4B 110.6 . . ?
C3 C4 H4B 110.6 . . ?
H4A C4 H4B 108.7 . . ?
N1 C5 C6 112.2(2) . . ?
N1 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
N1 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C5 113.0(2) . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
O2 C7 C6 122.9(3) . . ?
O2 C7 C8 122.6(3) . . ?
C6 C7 C8 114.5(2) . . ?
C7 C8 C9 109.7(2) . . ?
C7 C8 C1 108.4(2) . . ?
C9 C8 C1 109.1(2) . . ?
C7 C8 H8 109.9 . . ?
C9 C8 H8 109.9 . . ?
C1 C8 H8 109.9 . . ?
O1 C9 C8 113.1(2) . . ?
O1 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
O1 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
O3 C10 C11 103.4(2) . . ?
O3 C10 C12 110.9(2) . . ?
C11 C10 C12 111.1(2) . . ?
O3 C10 C13 110.4(2) . . ?
C11 C10 C13 110.3(3) . . ?
C12 C10 C13 110.5(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.042

_shelxl_version_number           2014/6



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_94
_database_code_depnum_ccdc_archive 'CCDC 1496579'
_audit_update_record             
;
2016-07-28 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             
;
'Tue May 10 12:33:38 2016'
;
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
(3R,4S,4aR,8aS,11R,12S,12aR,16aS)-4,12-di-tert-butoxydodecahydro-3,5:11,13-
dimethanodipyrano[4,3-b:4',3'-h][1,7]diazacyclododecine-8,16(3H,11H)-dione
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C26 H42 N2 O6)'
_chemical_formula_sum            'C52 H84 N4 O12'
_chemical_formula_weight         957.23
_chemical_absolute_configuration syn

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.2520(10)
_cell_length_b                   25.5700(10)
_cell_length_c                   14.4650(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.170(2)
_cell_angle_gamma                90
_cell_volume                     2640.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5427
_cell_measurement_theta_min      4.6420
_cell_measurement_theta_max      71.5950

_exptl_crystal_description       prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9530
_exptl_absorpt_correction_T_max  0.9796

_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1241
_diffrn_reflns_number            11770
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.648
_diffrn_reflns_theta_max         72.537
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.994
_reflns_number_total             7615
_reflns_number_gt                6330
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.492
_reflns_Friedel_fraction_max     0.492
_reflns_Friedel_fraction_full    0.532

_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -125.00  -90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.1574  -99.0000  -60.0000 35

#__ type_ start__ end____ width___ exp.time_
  2 omega  -22.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       46.1574  -37.0000  120.0000 87

#__ type_ start__ end____ width___ exp.time_
  3 omega   67.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       46.1574   37.0000 -120.0000 46

#__ type_ start__ end____ width___ exp.time_
  4 omega  -69.00  -35.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   30.0000  -30.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega  -53.00  -26.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   77.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega  -88.00  -59.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   77.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
  7 omega  -64.00  -29.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   45.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
  8 omega   37.00   71.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -45.0000   30.0000 34

#__ type_ start__ end____ width___ exp.time_
  9 omega   40.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -94.0000   30.0000 69

#__ type_ start__ end____ width___ exp.time_
 10 omega   67.00  167.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   15.0000  -30.0000 100

#__ type_ start__ end____ width___ exp.time_
 11 omega   28.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -30.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 12 omega   55.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000 -125.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
 13 omega   38.00   67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -30.0000  120.0000 29

;

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SIR2004 J.Appl.Cryst.38,381-388'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0694P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 x determined using 1810 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.25(16)
_refine_ls_number_reflns         7615
_refine_ls_number_parameters     613
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1250
_refine_ls_wR_factor_gt          0.1151
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 0.8991(4) 0.04439(14) 0.9299(2) 0.0252(7) Uani 1 1 d . . . . .
N2A N 0.6195(4) -0.11771(14) 0.7872(2) 0.0247(7) Uani 1 1 d . . . . .
O1A O 0.6009(4) 0.13089(11) 0.90142(19) 0.0284(6) Uani 1 1 d . . . . .
O2A O 0.8950(4) -0.19953(12) 0.7422(2) 0.0318(7) Uani 1 1 d . . . . .
O3A O 1.0210(4) -0.03972(12) 0.7839(2) 0.0321(7) Uani 1 1 d . . . . .
O4A O 0.5480(4) -0.04855(12) 0.9941(2) 0.0328(7) Uani 1 1 d . . . . .
O5A O 0.9855(4) 0.11279(12) 1.09635(19) 0.0309(7) Uani 1 1 d . . . . .
O6A O 0.5702(4) -0.20553(12) 0.9070(2) 0.0339(7) Uani 1 1 d . . . . .
C1A C 0.7835(5) 0.04729(17) 1.0040(3) 0.0261(9) Uani 1 1 d . . . . .
H1A H 0.8209 0.0213 1.0535 0.031 Uiso 1 1 calc R U . . .
C2A C 0.8063(5) 0.10372(17) 1.0415(3) 0.0271(9) Uani 1 1 d . . . . .
H2A H 0.7049 0.1139 1.0745 0.033 Uiso 1 1 calc R U . . .
C3A C 0.7939(5) 0.13171(18) 0.9477(3) 0.0271(9) Uani 1 1 d . . . . .
H3A H 0.8398 0.1677 0.9569 0.032 Uiso 1 1 calc R U . . .
C4A C 0.5343(6) 0.07930(17) 0.8746(3) 0.0288(9) Uani 1 1 d . . . . .
H4A1 H 0.5934 0.0671 0.8234 0.035 Uiso 1 1 calc R U . . .
H4A2 H 0.4002 0.0806 0.8521 0.035 Uiso 1 1 calc R U . . .
C5A C 0.5756(5) 0.04099(17) 0.9560(3) 0.0244(8) Uani 1 1 d . . . . .
H5A H 0.4971 0.0506 1.0019 0.029 Uiso 1 1 calc R U . . .
C6A C 0.9238(6) 0.09910(17) 0.8993(3) 0.0290(9) Uani 1 1 d . . . . .
H6A1 H 0.8898 0.1021 0.8316 0.035 Uiso 1 1 calc R U . . .
H6A2 H 1.0527 0.1103 0.9183 0.035 Uiso 1 1 calc R U . . .
C7A C 0.5392(5) -0.01659(17) 0.9309(3) 0.0259(9) Uani 1 1 d . . . . .
C8A C 0.4947(5) -0.03201(17) 0.8293(3) 0.0264(9) Uani 1 1 d . . . . .
H8A1 H 0.5987 -0.0214 0.7997 0.032 Uiso 1 1 calc R U . . .
H8A2 H 0.3859 -0.0122 0.8000 0.032 Uiso 1 1 calc R U . . .
C9A C 0.4560(5) -0.08962(17) 0.8074(3) 0.0259(9) Uani 1 1 d . . . . .
H9A1 H 0.4142 -0.1060 0.8605 0.031 Uiso 1 1 calc R U . . .
H9A2 H 0.3554 -0.0925 0.7537 0.031 Uiso 1 1 calc R U . . .
C10A C 0.7612(5) -0.13356(17) 0.8695(3) 0.0259(9) Uani 1 1 d . . . . .
H10A H 0.7424 -0.1160 0.9273 0.031 Uiso 1 1 calc R U . . .
C11A C 0.7386(6) -0.19263(17) 0.8751(3) 0.0279(9) Uani 1 1 d . . . . .
H11A H 0.8482 -0.2093 0.9129 0.034 Uiso 1 1 calc R U . . .
C12A C 0.7198(6) -0.20580(18) 0.7715(3) 0.0301(9) Uani 1 1 d . . . . .
H12A H 0.6719 -0.2414 0.7589 0.036 Uiso 1 1 calc R U . . .
C13A C 0.5731(6) -0.16532(17) 0.7297(3) 0.0291(9) Uani 1 1 d . . . . .
H13A H 0.5802 -0.1585 0.6644 0.035 Uiso 1 1 calc R U . . .
H13B H 0.4479 -0.1774 0.7334 0.035 Uiso 1 1 calc R U . . .
C14A C 0.9656(6) -0.14666(18) 0.7504(3) 0.0318(10) Uani 1 1 d . . . . .
H14A H 0.8913 -0.1251 0.7026 0.038 Uiso 1 1 calc R U . . .
H14B H 1.0937 -0.1464 0.7395 0.038 Uiso 1 1 calc R U . . .
C15A C 0.9598(5) -0.12336(17) 0.8467(3) 0.0275(9) Uani 1 1 d . . . . .
H15A H 1.0510 -0.1421 0.8931 0.033 Uiso 1 1 calc R U . . .
C16A C 1.0095(5) -0.06567(17) 0.8530(3) 0.0272(9) Uani 1 1 d . . . . .
C17A C 1.0523(5) -0.04279(17) 0.9514(3) 0.0286(9) Uani 1 1 d . . . . .
H17A H 0.9511 -0.0519 0.9842 0.034 Uiso 1 1 calc R U . . .
H17B H 1.1657 -0.0590 0.9848 0.034 Uiso 1 1 calc R U . . .
C18A C 1.0776(5) 0.01586(17) 0.9552(3) 0.0296(9) Uani 1 1 d . . . . .
H18A H 1.1368 0.0258 1.0181 0.035 Uiso 1 1 calc R U . . .
H18B H 1.1606 0.0260 0.9125 0.035 Uiso 1 1 calc R U . . .
C19A C 0.5891(7) -0.23254(18) 0.9966(3) 0.0352(10) Uani 1 1 d . . . . .
C20A C 0.3881(7) -0.2341(2) 1.0142(4) 0.0451(12) Uani 1 1 d . . . . .
H20A H 0.3849 -0.2515 1.0728 0.068 Uiso 1 1 calc R U . . .
H20B H 0.3419 -0.1991 1.0169 0.068 Uiso 1 1 calc R U . . .
H20C H 0.3111 -0.2528 0.9642 0.068 Uiso 1 1 calc R U . . .
C21A C 0.7113(8) -0.2010(2) 1.0733(3) 0.0479(13) Uani 1 1 d . . . . .
H21A H 0.7225 -0.2193 1.1320 0.072 Uiso 1 1 calc R U . . .
H21B H 0.8334 -0.1964 1.0575 0.072 Uiso 1 1 calc R U . . .
H21C H 0.6551 -0.1674 1.0789 0.072 Uiso 1 1 calc R U . . .
C22A C 0.6638(8) -0.28729(19) 0.9870(4) 0.0467(13) Uani 1 1 d . . . . .
H22A H 0.6761 -0.3050 1.0462 0.070 Uiso 1 1 calc R U . . .
H22B H 0.5785 -0.3062 0.9405 0.070 Uiso 1 1 calc R U . . .
H22C H 0.7840 -0.2853 0.9681 0.070 Uiso 1 1 calc R U . . .
C23A C 0.9914(6) 0.11764(19) 1.1974(3) 0.0363(10) Uani 1 1 d . . . . .
C24A C 0.8942(8) 0.1671(2) 1.2197(4) 0.0511(13) Uani 1 1 d . . . . .
H24A H 0.8994 0.1696 1.2864 0.077 Uiso 1 1 calc R U . . .
H24B H 0.9556 0.1968 1.1983 0.077 Uiso 1 1 calc R U . . .
H24C H 0.7657 0.1663 1.1888 0.077 Uiso 1 1 calc R U . . .
C25A C 1.2013(6) 0.1212(2) 1.2360(3) 0.0389(11) Uani 1 1 d . . . . .
H25A H 1.2208 0.1245 1.3031 0.058 Uiso 1 1 calc R U . . .
H25B H 1.2623 0.0901 1.2195 0.058 Uiso 1 1 calc R U . . .
H25C H 1.2527 0.1511 1.2096 0.058 Uiso 1 1 calc R U . . .
C26A C 0.9096(7) 0.0691(2) 1.2357(3) 0.0454(13) Uani 1 1 d . . . . .
H26A H 0.9145 0.0729 1.3021 0.068 Uiso 1 1 calc R U . . .
H26B H 0.7818 0.0648 1.2052 0.068 Uiso 1 1 calc R U . . .
H26C H 0.9810 0.0390 1.2240 0.068 Uiso 1 1 calc R U . . .
N1B N 0.3030(4) 0.15114(13) 0.6690(2) 0.0250(7) Uani 1 1 d . . . . .
N2B N 0.5058(4) -0.00335(13) 0.5243(2) 0.0245(7) Uani 1 1 d . . . . .
O1B O 0.5858(4) 0.24142(11) 0.7029(2) 0.0297(6) Uani 1 1 d . . . . .
O2B O 0.2392(4) -0.09557(11) 0.5450(2) 0.0285(6) Uani 1 1 d . . . . .
O3B O 0.7065(4) 0.08429(12) 0.66554(19) 0.0302(6) Uani 1 1 d . . . . .
O4B O 0.0908(4) 0.08411(12) 0.46449(19) 0.0301(6) Uani 1 1 d . . . . .
O5B O 0.1225(4) 0.23250(11) 0.54891(19) 0.0282(6) Uani 1 1 d . . . . .
O6B O 0.5103(4) -0.06888(12) 0.36320(18) 0.0289(6) Uani 1 1 d . . . . .
C1B C 0.3662(5) 0.17046(16) 0.5839(3) 0.0249(8) Uani 1 1 d . . . . .
H1B H 0.3053 0.1520 0.5274 0.030 Uiso 1 1 calc R U . . .
C2B C 0.3208(5) 0.22859(17) 0.5794(3) 0.0254(9) Uani 1 1 d . . . . .
H2B H 0.3913 0.2478 0.5384 0.030 Uiso 1 1 calc R U . . .
C3B C 0.3853(5) 0.24174(17) 0.6831(3) 0.0269(9) Uani 1 1 d . . . . .
H3B H 0.3359 0.2757 0.6986 0.032 Uiso 1 1 calc R U . . .
C4B C 0.6640(6) 0.19085(17) 0.6932(3) 0.0285(9) Uani 1 1 d . . . . .
H4B1 H 0.6388 0.1685 0.7437 0.034 Uiso 1 1 calc R U . . .
H4B2 H 0.7988 0.1940 0.6988 0.034 Uiso 1 1 calc R U . . .
C5B C 0.5842(5) 0.16538(16) 0.5992(3) 0.0256(9) Uani 1 1 d . . . . .
H5B H 0.6297 0.1847 0.5492 0.031 Uiso 1 1 calc R U . . .
C6B C 0.2969(6) 0.19711(17) 0.7305(3) 0.0271(9) Uani 1 1 d . . . . .
H6B1 H 0.3675 0.1905 0.7929 0.032 Uiso 1 1 calc R U . . .
H6B2 H 0.1687 0.2055 0.7358 0.032 Uiso 1 1 calc R U . . .
C7B C 0.6432(5) 0.10871(17) 0.5949(3) 0.0250(9) Uani 1 1 d . . . . .
C8B C 0.6288(5) 0.08477(17) 0.4984(3) 0.0267(9) Uani 1 1 d . . . . .
H8B1 H 0.7196 0.1015 0.4663 0.032 Uiso 1 1 calc R U . . .
H8B2 H 0.5052 0.0920 0.4627 0.032 Uiso 1 1 calc R U . . .
C9B C 0.6617(5) 0.02620(17) 0.4993(3) 0.0258(9) Uani 1 1 d . . . . .
H9B1 H 0.6816 0.0152 0.4376 0.031 Uiso 1 1 calc R U . . .
H9B2 H 0.7745 0.0182 0.5439 0.031 Uiso 1 1 calc R U . . .
C10B C 0.3405(5) -0.00789(16) 0.4486(3) 0.0244(8) Uani 1 1 d . . . . .
H10B H 0.3402 0.0190 0.4004 0.029 Uiso 1 1 calc R U . . .
C11B C 0.3536(5) -0.06292(17) 0.4089(3) 0.0271(9) Uani 1 1 d . . . . .
H11B H 0.2360 -0.0746 0.3703 0.033 Uiso 1 1 calc R U . . .
C12B C 0.4016(5) -0.09258(17) 0.5019(3) 0.0260(9) Uani 1 1 d . . . . .
H12B H 0.4495 -0.1276 0.4919 0.031 Uiso 1 1 calc R U . . .
C13B C 0.5579(5) -0.05755(16) 0.5545(3) 0.0255(9) Uani 1 1 d . . . . .
H13C H 0.5660 -0.0611 0.6219 0.031 Uiso 1 1 calc R U . . .
H13D H 0.6779 -0.0669 0.5384 0.031 Uiso 1 1 calc R U . . .
C14B C 0.1791(5) -0.04530(17) 0.5731(3) 0.0275(9) Uani 1 1 d . . . . .
H14C H 0.2683 -0.0327 0.6264 0.033 Uiso 1 1 calc R U . . .
H14D H 0.0587 -0.0490 0.5928 0.033 Uiso 1 1 calc R U . . .
C15B C 0.1621(5) -0.00524(16) 0.4936(3) 0.0245(8) Uani 1 1 d . . . . .
H15B H 0.0544 -0.0149 0.4456 0.029 Uiso 1 1 calc R U . . .
C16B C 0.1337(5) 0.05073(16) 0.5242(3) 0.0240(8) Uani 1 1 d . . . . .
C17B C 0.1635(5) 0.06364(16) 0.6277(3) 0.0261(9) Uani 1 1 d . . . . .
H17C H 0.2911 0.0544 0.6551 0.031 Uiso 1 1 calc R U . . .
H17D H 0.0810 0.0416 0.6568 0.031 Uiso 1 1 calc R U . . .
C18B C 0.1305(5) 0.12036(16) 0.6533(3) 0.0259(9) Uani 1 1 d . . . . .
H18C H 0.0418 0.1362 0.6031 0.031 Uiso 1 1 calc R U . . .
H18D H 0.0756 0.1211 0.7098 0.031 Uiso 1 1 calc R U . . .
C19B C 0.4812(6) -0.07079(18) 0.2613(3) 0.0327(10) Uani 1 1 d . . . . .
C20B C 0.3613(7) -0.1176(2) 0.2240(3) 0.0440(12) Uani 1 1 d . . . . .
H20D H 0.3440 -0.1180 0.1566 0.066 Uiso 1 1 calc R U . . .
H20E H 0.4227 -0.1492 0.2485 0.066 Uiso 1 1 calc R U . . .
H20F H 0.2416 -0.1151 0.2433 0.066 Uiso 1 1 calc R U . . .
C21B C 0.3949(7) -0.0201(2) 0.2197(3) 0.0422(12) Uani 1 1 d . . . . .
H21D H 0.3766 -0.0220 0.1524 0.063 Uiso 1 1 calc R U . . .
H21E H 0.2764 -0.0147 0.2391 0.063 Uiso 1 1 calc R U . . .
H21F H 0.4772 0.0085 0.2411 0.063 Uiso 1 1 calc R U . . .
C22B C 0.6784(7) -0.0762(2) 0.2417(3) 0.0410(12) Uani 1 1 d . . . . .
H22D H 0.6748 -0.0778 0.1751 0.062 Uiso 1 1 calc R U . . .
H22E H 0.7515 -0.0465 0.2671 0.062 Uiso 1 1 calc R U . . .
H22F H 0.7340 -0.1076 0.2704 0.062 Uiso 1 1 calc R U . . .
C23B C -0.1259(6) 0.27315(19) 0.4484(3) 0.0337(10) Uani 1 1 d . . . . .
H23A H -0.1931 0.3050 0.4308 0.051 Uiso 1 1 calc R U . . .
H23B H -0.0758 0.2600 0.3958 0.051 Uiso 1 1 calc R U . . .
H23C H -0.2095 0.2477 0.4672 0.051 Uiso 1 1 calc R U . . .
C24B C 0.1659(6) 0.32488(18) 0.5024(3) 0.0314(9) Uani 1 1 d . . . . .
H24D H 0.1008 0.3576 0.4909 0.047 Uiso 1 1 calc R U . . .
H24E H 0.2712 0.3291 0.5523 0.047 Uiso 1 1 calc R U . . .
H24F H 0.2090 0.3139 0.4464 0.047 Uiso 1 1 calc R U . . .
C25B C 0.0340(5) 0.28386(17) 0.5301(3) 0.0279(9) Uani 1 1 d . . . . .
C26B C -0.0445(6) 0.30183(19) 0.6159(3) 0.0330(10) Uani 1 1 d . . . . .
H26D H -0.1025 0.3355 0.6036 0.050 Uiso 1 1 calc R U . . .
H26E H -0.1359 0.2771 0.6291 0.050 Uiso 1 1 calc R U . . .
H26F H 0.0553 0.3043 0.6690 0.050 Uiso 1 1 calc R U . . .


_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
N1A C1A 1.474(5) . ?
N1A C18A 1.475(5) . ?
N1A C6A 1.487(6) . ?
N2A C9A 1.459(5) . ?
N2A C13A 1.479(5) . ?
N2A C10A 1.486(5) . ?
O1A C4A 1.435(5) . ?
O1A C3A 1.441(5) . ?
O2A C12A 1.417(5) . ?
O2A C14A 1.443(5) . ?
O3A C16A 1.215(5) . ?
O4A C7A 1.220(5) . ?
O5A C2A 1.417(5) . ?
O5A C23A 1.460(5) . ?
O6A C11A 1.418(5) . ?
O6A C19A 1.453(5) . ?
C1A C2A 1.540(6) . ?
C1A C5A 1.553(5) . ?
C1A H1A 0.9800 . ?
C2A C3A 1.523(6) . ?
C2A H2A 0.9800 . ?
C3A C6A 1.518(6) . ?
C3A H3A 0.9800 . ?
C4A C5A 1.520(6) . ?
C4A H4A1 0.9700 . ?
C4A H4A2 0.9700 . ?
C5A C7A 1.528(6) . ?
C5A H5A 0.9800 . ?
C6A H6A1 0.9700 . ?
C6A H6A2 0.9700 . ?
C7A C8A 1.500(5) . ?
C8A C9A 1.522(6) . ?
C8A H8A1 0.9700 . ?
C8A H8A2 0.9700 . ?
C9A H9A1 0.9700 . ?
C9A H9A2 0.9700 . ?
C10A C11A 1.523(6) . ?
C10A C15A 1.556(5) . ?
C10A H10A 0.9800 . ?
C11A C12A 1.518(6) . ?
C11A H11A 0.9800 . ?
C12A C13A 1.530(6) . ?
C12A H12A 0.9800 . ?
C13A H13A 0.9700 . ?
C13A H13B 0.9700 . ?
C14A C15A 1.522(6) . ?
C14A H14A 0.9700 . ?
C14A H14B 0.9700 . ?
C15A C16A 1.517(6) . ?
C15A H15A 0.9800 . ?
C16A C17A 1.519(6) . ?
C17A C18A 1.511(6) . ?
C17A H17A 0.9700 . ?
C17A H17B 0.9700 . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C19A C22A 1.516(7) . ?
C19A C21A 1.523(7) . ?
C19A C20A 1.524(7) . ?
C20A H20A 0.9600 . ?
C20A H20B 0.9600 . ?
C20A H20C 0.9600 . ?
C21A H21A 0.9600 . ?
C21A H21B 0.9600 . ?
C21A H21C 0.9600 . ?
C22A H22A 0.9600 . ?
C22A H22B 0.9600 . ?
C22A H22C 0.9600 . ?
C23A C24A 1.510(7) . ?
C23A C26A 1.522(7) . ?
C23A C25A 1.529(6) . ?
C24A H24A 0.9600 . ?
C24A H24B 0.9600 . ?
C24A H24C 0.9600 . ?
C25A H25A 0.9600 . ?
C25A H25B 0.9600 . ?
C25A H25C 0.9600 . ?
C26A H26A 0.9600 . ?
C26A H26B 0.9600 . ?
C26A H26C 0.9600 . ?
N1B C18B 1.461(5) . ?
N1B C1B 1.472(5) . ?
N1B C6B 1.480(5) . ?
N2B C9B 1.457(5) . ?
N2B C10B 1.479(5) . ?
N2B C13B 1.482(5) . ?
O1B C4B 1.429(5) . ?
O1B C3B 1.432(5) . ?
O2B C12B 1.429(5) . ?
O2B C14B 1.438(5) . ?
O3B C7B 1.216(5) . ?
O4B C16B 1.215(5) . ?
O5B C2B 1.431(5) . ?
O5B C25B 1.466(5) . ?
O6B C11B 1.420(5) . ?
O6B C19B 1.452(5) . ?
C1B C2B 1.521(6) . ?
C1B C5B 1.562(5) . ?
C1B H1B 0.9800 . ?
C2B C3B 1.528(6) . ?
C2B H2B 0.9800 . ?
C3B C6B 1.529(6) . ?
C3B H3B 0.9800 . ?
C4B C5B 1.527(6) . ?
C4B H4B1 0.9700 . ?
C4B H4B2 0.9700 . ?
C5B C7B 1.515(6) . ?
C5B H5B 0.9800 . ?
C6B H6B1 0.9700 . ?
C6B H6B2 0.9700 . ?
C7B C8B 1.511(6) . ?
C8B C9B 1.516(6) . ?
C8B H8B1 0.9700 . ?
C8B H8B2 0.9700 . ?
C9B H9B1 0.9700 . ?
C9B H9B2 0.9700 . ?
C10B C11B 1.529(6) . ?
C10B C15B 1.549(5) . ?
C10B H10B 0.9800 . ?
C11B C12B 1.529(6) . ?
C11B H11B 0.9800 . ?
C12B C13B 1.537(6) . ?
C12B H12B 0.9800 . ?
C13B H13C 0.9700 . ?
C13B H13D 0.9700 . ?
C14B C15B 1.528(6) . ?
C14B H14C 0.9700 . ?
C14B H14D 0.9700 . ?
C15B C16B 1.523(6) . ?
C15B H15B 0.9800 . ?
C16B C17B 1.510(5) . ?
C17B C18B 1.526(6) . ?
C17B H17C 0.9700 . ?
C17B H17D 0.9700 . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
C19B C22B 1.513(6) . ?
C19B C21B 1.517(6) . ?
C19B C20B 1.521(7) . ?
C20B H20D 0.9600 . ?
C20B H20E 0.9600 . ?
C20B H20F 0.9600 . ?
C21B H21D 0.9600 . ?
C21B H21E 0.9600 . ?
C21B H21F 0.9600 . ?
C22B H22D 0.9600 . ?
C22B H22E 0.9600 . ?
C22B H22F 0.9600 . ?
C23B C25B 1.527(6) . ?
C23B H23A 0.9600 . ?
C23B H23B 0.9600 . ?
C23B H23C 0.9600 . ?
C24B C25B 1.520(6) . ?
C24B H24D 0.9600 . ?
C24B H24E 0.9600 . ?
C24B H24F 0.9600 . ?
C25B C26B 1.525(6) . ?
C26B H26D 0.9600 . ?
C26B H26E 0.9600 . ?
C26B H26F 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
C1A N1A C18A 115.6(3) . . ?
C1A N1A C6A 106.4(3) . . ?
C18A N1A C6A 113.1(3) . . ?
C9A N2A C13A 113.9(3) . . ?
C9A N2A C10A 116.4(3) . . ?
C13A N2A C10A 106.4(3) . . ?
C4A O1A C3A 113.1(3) . . ?
C12A O2A C14A 113.9(3) . . ?
C2A O5A C23A 115.8(3) . . ?
C11A O6A C19A 116.7(3) . . ?
N1A C1A C2A 105.3(3) . . ?
N1A C1A C5A 107.5(3) . . ?
C2A C1A C5A 106.9(3) . . ?
N1A C1A H1A 112.2 . . ?
C2A C1A H1A 112.2 . . ?
C5A C1A H1A 112.2 . . ?
O5A C2A C3A 109.0(3) . . ?
O5A C2A C1A 112.4(3) . . ?
C3A C2A C1A 98.0(3) . . ?
O5A C2A H2A 112.2 . . ?
C3A C2A H2A 112.2 . . ?
C1A C2A H2A 112.2 . . ?
O1A C3A C6A 114.1(3) . . ?
O1A C3A C2A 107.9(3) . . ?
C6A C3A C2A 102.1(3) . . ?
O1A C3A H3A 110.8 . . ?
C6A C3A H3A 110.8 . . ?
C2A C3A H3A 110.8 . . ?
O1A C4A C5A 111.8(3) . . ?
O1A C4A H4A1 109.2 . . ?
C5A C4A H4A1 109.2 . . ?
O1A C4A H4A2 109.2 . . ?
C5A C4A H4A2 109.2 . . ?
H4A1 C4A H4A2 107.9 . . ?
C4A C5A C7A 115.8(3) . . ?
C4A C5A C1A 108.8(3) . . ?
C7A C5A C1A 108.6(3) . . ?
C4A C5A H5A 107.8 . . ?
C7A C5A H5A 107.8 . . ?
C1A C5A H5A 107.8 . . ?
N1A C6A C3A 105.2(3) . . ?
N1A C6A H6A1 110.7 . . ?
C3A C6A H6A1 110.7 . . ?
N1A C6A H6A2 110.7 . . ?
C3A C6A H6A2 110.7 . . ?
H6A1 C6A H6A2 108.8 . . ?
O4A C7A C8A 122.2(4) . . ?
O4A C7A C5A 118.9(4) . . ?
C8A C7A C5A 118.9(3) . . ?
C7A C8A C9A 117.3(3) . . ?
C7A C8A H8A1 108.0 . . ?
C9A C8A H8A1 108.0 . . ?
C7A C8A H8A2 108.0 . . ?
C9A C8A H8A2 108.0 . . ?
H8A1 C8A H8A2 107.2 . . ?
N2A C9A C8A 113.1(3) . . ?
N2A C9A H9A1 109.0 . . ?
C8A C9A H9A1 109.0 . . ?
N2A C9A H9A2 109.0 . . ?
C8A C9A H9A2 109.0 . . ?
H9A1 C9A H9A2 107.8 . . ?
N2A C10A C11A 104.3(3) . . ?
N2A C10A C15A 108.6(3) . . ?
C11A C10A C15A 106.9(3) . . ?
N2A C10A H10A 112.2 . . ?
C11A C10A H10A 112.2 . . ?
C15A C10A H10A 112.2 . . ?
O6A C11A C12A 109.7(3) . . ?
O6A C11A C10A 110.8(3) . . ?
C12A C11A C10A 99.2(3) . . ?
O6A C11A H11A 112.2 . . ?
C12A C11A H11A 112.2 . . ?
C10A C11A H11A 112.2 . . ?
O2A C12A C11A 109.9(3) . . ?
O2A C12A C13A 113.7(3) . . ?
C11A C12A C13A 100.1(3) . . ?
O2A C12A H12A 110.9 . . ?
C11A C12A H12A 110.9 . . ?
C13A C12A H12A 110.9 . . ?
N2A C13A C12A 105.1(3) . . ?
N2A C13A H13A 110.7 . . ?
C12A C13A H13A 110.7 . . ?
N2A C13A H13B 110.7 . . ?
C12A C13A H13B 110.7 . . ?
H13A C13A H13B 108.8 . . ?
O2A C14A C15A 112.0(3) . . ?
O2A C14A H14A 109.2 . . ?
C15A C14A H14A 109.2 . . ?
O2A C14A H14B 109.2 . . ?
C15A C14A H14B 109.2 . . ?
H14A C14A H14B 107.9 . . ?
C16A C15A C14A 113.0(3) . . ?
C16A C15A C10A 111.7(3) . . ?
C14A C15A C10A 107.7(3) . . ?
C16A C15A H15A 108.1 . . ?
C14A C15A H15A 108.1 . . ?
C10A C15A H15A 108.1 . . ?
O3A C16A C15A 122.1(4) . . ?
O3A C16A C17A 121.9(4) . . ?
C15A C16A C17A 115.9(3) . . ?
C18A C17A C16A 114.8(4) . . ?
C18A C17A H17A 108.6 . . ?
C16A C17A H17A 108.6 . . ?
C18A C17A H17B 108.6 . . ?
C16A C17A H17B 108.6 . . ?
H17A C17A H17B 107.5 . . ?
N1A C18A C17A 112.7(3) . . ?
N1A C18A H18A 109.0 . . ?
C17A C18A H18A 109.0 . . ?
N1A C18A H18B 109.0 . . ?
C17A C18A H18B 109.0 . . ?
H18A C18A H18B 107.8 . . ?
O6A C19A C22A 109.6(3) . . ?
O6A C19A C21A 110.5(4) . . ?
C22A C19A C21A 112.6(4) . . ?
O6A C19A C20A 102.7(4) . . ?
C22A C19A C20A 111.0(4) . . ?
C21A C19A C20A 110.0(4) . . ?
C19A C20A H20A 109.5 . . ?
C19A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C19A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C19A C21A H21A 109.5 . . ?
C19A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
C19A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C19A C22A H22A 109.5 . . ?
C19A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C19A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
O5A C23A C24A 110.7(4) . . ?
O5A C23A C26A 110.6(4) . . ?
C24A C23A C26A 112.2(4) . . ?
O5A C23A C25A 102.8(3) . . ?
C24A C23A C25A 110.2(4) . . ?
C26A C23A C25A 110.0(4) . . ?
C23A C24A H24A 109.5 . . ?
C23A C24A H24B 109.5 . . ?
H24A C24A H24B 109.5 . . ?
C23A C24A H24C 109.5 . . ?
H24A C24A H24C 109.5 . . ?
H24B C24A H24C 109.5 . . ?
C23A C25A H25A 109.5 . . ?
C23A C25A H25B 109.5 . . ?
H25A C25A H25B 109.5 . . ?
C23A C25A H25C 109.5 . . ?
H25A C25A H25C 109.5 . . ?
H25B C25A H25C 109.5 . . ?
C23A C26A H26A 109.5 . . ?
C23A C26A H26B 109.5 . . ?
H26A C26A H26B 109.5 . . ?
C23A C26A H26C 109.5 . . ?
H26A C26A H26C 109.5 . . ?
H26B C26A H26C 109.5 . . ?
C18B N1B C1B 115.8(3) . . ?
C18B N1B C6B 113.9(3) . . ?
C1B N1B C6B 106.5(3) . . ?
C9B N2B C10B 114.8(3) . . ?
C9B N2B C13B 112.9(3) . . ?
C10B N2B C13B 106.0(3) . . ?
C4B O1B C3B 113.1(3) . . ?
C12B O2B C14B 112.9(3) . . ?
C2B O5B C25B 120.2(3) . . ?
C11B O6B C19B 119.4(3) . . ?
N1B C1B C2B 105.5(3) . . ?
N1B C1B C5B 108.1(3) . . ?
C2B C1B C5B 107.1(3) . . ?
N1B C1B H1B 112.0 . . ?
C2B C1B H1B 112.0 . . ?
C5B C1B H1B 112.0 . . ?
O5B C2B C1B 106.2(3) . . ?
O5B C2B C3B 113.8(3) . . ?
C1B C2B C3B 98.4(3) . . ?
O5B C2B H2B 112.5 . . ?
C1B C2B H2B 112.5 . . ?
C3B C2B H2B 112.5 . . ?
O1B C3B C6B 113.4(3) . . ?
O1B C3B C2B 108.6(3) . . ?
C6B C3B C2B 101.3(3) . . ?
O1B C3B H3B 111.0 . . ?
C6B C3B H3B 111.0 . . ?
C2B C3B H3B 111.0 . . ?
O1B C4B C5B 112.3(3) . . ?
O1B C4B H4B1 109.1 . . ?
C5B C4B H4B1 109.1 . . ?
O1B C4B H4B2 109.1 . . ?
C5B C4B H4B2 109.1 . . ?
H4B1 C4B H4B2 107.9 . . ?
C7B C5B C4B 112.3(3) . . ?
C7B C5B C1B 111.1(3) . . ?
C4B C5B C1B 107.8(3) . . ?
C7B C5B H5B 108.5 . . ?
C4B C5B H5B 108.5 . . ?
C1B C5B H5B 108.5 . . ?
N1B C6B C3B 105.3(3) . . ?
N1B C6B H6B1 110.7 . . ?
C3B C6B H6B1 110.7 . . ?
N1B C6B H6B2 110.7 . . ?
C3B C6B H6B2 110.7 . . ?
H6B1 C6B H6B2 108.8 . . ?
O3B C7B C8B 121.5(4) . . ?
O3B C7B C5B 121.6(4) . . ?
C8B C7B C5B 116.8(3) . . ?
C7B C8B C9B 114.0(3) . . ?
C7B C8B H8B1 108.7 . . ?
C9B C8B H8B1 108.7 . . ?
C7B C8B H8B2 108.7 . . ?
C9B C8B H8B2 108.7 . . ?
H8B1 C8B H8B2 107.6 . . ?
N2B C9B C8B 112.8(3) . . ?
N2B C9B H9B1 109.0 . . ?
C8B C9B H9B1 109.0 . . ?
N2B C9B H9B2 109.0 . . ?
C8B C9B H9B2 109.0 . . ?
H9B1 C9B H9B2 107.8 . . ?
N2B C10B C11B 104.7(3) . . ?
N2B C10B C15B 108.3(3) . . ?
C11B C10B C15B 108.1(3) . . ?
N2B C10B H10B 111.8 . . ?
C11B C10B H10B 111.8 . . ?
C15B C10B H10B 111.8 . . ?
O6B C11B C10B 112.4(3) . . ?
O6B C11B C12B 106.2(3) . . ?
C10B C11B C12B 98.4(3) . . ?
O6B C11B H11B 112.9 . . ?
C10B C11B H11B 112.9 . . ?
C12B C11B H11B 112.9 . . ?
O2B C12B C11B 109.5(3) . . ?
O2B C12B C13B 114.0(3) . . ?
C11B C12B C13B 100.4(3) . . ?
O2B C12B H12B 110.8 . . ?
C11B C12B H12B 110.8 . . ?
C13B C12B H12B 110.8 . . ?
N2B C13B C12B 105.8(3) . . ?
N2B C13B H13C 110.6 . . ?
C12B C13B H13C 110.6 . . ?
N2B C13B H13D 110.6 . . ?
C12B C13B H13D 110.6 . . ?
H13C C13B H13D 108.7 . . ?
O2B C14B C15B 112.0(3) . . ?
O2B C14B H14C 109.2 . . ?
C15B C14B H14C 109.2 . . ?
O2B C14B H14D 109.2 . . ?
C15B C14B H14D 109.2 . . ?
H14C C14B H14D 107.9 . . ?
C16B C15B C14B 114.1(3) . . ?
C16B C15B C10B 109.2(3) . . ?
C14B C15B C10B 108.9(3) . . ?
C16B C15B H15B 108.2 . . ?
C14B C15B H15B 108.2 . . ?
C10B C15B H15B 108.2 . . ?
O4B C16B C17B 121.7(4) . . ?
O4B C16B C15B 118.9(3) . . ?
C17B C16B C15B 119.4(3) . . ?
C16B C17B C18B 116.6(3) . . ?
C16B C17B H17C 108.2 . . ?
C18B C17B H17C 108.2 . . ?
C16B C17B H17D 108.2 . . ?
C18B C17B H17D 108.2 . . ?
H17C C17B H17D 107.3 . . ?
N1B C18B C17B 112.5(3) . . ?
N1B C18B H18C 109.1 . . ?
C17B C18B H18C 109.1 . . ?
N1B C18B H18D 109.1 . . ?
C17B C18B H18D 109.1 . . ?
H18C C18B H18D 107.8 . . ?
O6B C19B C22B 102.7(3) . . ?
O6B C19B C21B 110.5(3) . . ?
C22B C19B C21B 109.9(4) . . ?
O6B C19B C20B 111.0(4) . . ?
C22B C19B C20B 111.2(4) . . ?
C21B C19B C20B 111.2(4) . . ?
C19B C20B H20D 109.5 . . ?
C19B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C19B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C19B C21B H21D 109.5 . . ?
C19B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
C19B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C19B C22B H22D 109.5 . . ?
C19B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C19B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
C25B C23B H23A 109.5 . . ?
C25B C23B H23B 109.5 . . ?
H23A C23B H23B 109.5 . . ?
C25B C23B H23C 109.5 . . ?
H23A C23B H23C 109.5 . . ?
H23B C23B H23C 109.5 . . ?
C25B C24B H24D 109.5 . . ?
C25B C24B H24E 109.5 . . ?
H24D C24B H24E 109.5 . . ?
C25B C24B H24F 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?
O5B C25B C26B 109.4(3) . . ?
O5B C25B C24B 113.1(3) . . ?
C26B C25B C24B 110.4(4) . . ?
O5B C25B C23B 103.4(3) . . ?
C26B C25B C23B 110.0(3) . . ?
C24B C25B C23B 110.3(4) . . ?
C25B C26B H26D 109.5 . . ?
C25B C26B H26E 109.5 . . ?
H26D C26B H26E 109.5 . . ?
C25B C26B H26F 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.053

_shelxl_version_number           2014/6



