# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_cu-1356
_database_code_depnum_ccdc_archive 'CCDC 1554475'
_audit_update_record             
;
2017-06-06 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_method           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_chemical_name_systematic        
'Dimethyl (r,s)-1-acetylpyrrolidine-2,5-dicarboxylate'
_chemical_name_common            ?
_chemical_melting_point          335
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H15 N O5'
_chemical_formula_weight         229.23

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pna21

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

_cell_length_a                   13.0145(3)
_cell_length_b                   7.79931(17)
_cell_length_c                   10.8094(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1097.21(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2649
_cell_measurement_theta_min      6.6140
_cell_measurement_theta_max      73.6260

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6484
_exptl_absorpt_correction_T_max  0.9453
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5435
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3683
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         6.62
_diffrn_reflns_theta_max         67.42
_reflns_number_total             1537
_reflns_number_gt                1505
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0333P)²+0.1969P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(18)
_refine_ls_number_reflns         1537
_refine_ls_number_parameters     147
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0632
_refine_ls_wR_factor_gt          0.0626
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.46156(9) 0.47238(15) 0.11025(14) 0.0213(3) Uani 1 1 d . . .
O1 O 0.29773(8) 0.42068(14) 0.05878(13) 0.0281(3) Uani 1 1 d . . .
O2 O 0.52618(10) 0.65027(16) 0.32217(14) 0.0367(3) Uani 1 1 d . . .
O3 O 0.64821(8) 0.78464(14) 0.21348(13) 0.0303(3) Uani 1 1 d . . .
O4 O 0.37486(10) 0.31315(14) 0.32159(13) 0.0323(3) Uani 1 1 d . . .
O5 O 0.41617(9) 0.05530(13) 0.24503(15) 0.0328(3) Uani 1 1 d . . .
C1 C 0.55641(11) 0.57190(19) 0.10789(17) 0.0227(3) Uani 1 1 d . . .
H1A H 0.5561 0.6524 0.0359 0.027 Uiso 1 1 calc R . .
C2 C 0.63829(12) 0.4324(2) 0.08904(18) 0.0275(4) Uani 1 1 d . . .
H2A H 0.6464 0.4040 0.0003 0.033 Uiso 1 1 calc R . .
H2B H 0.7055 0.4689 0.1228 0.033 Uiso 1 1 calc R . .
C3 C 0.59515(12) 0.2808(2) 0.16109(19) 0.0269(4) Uani 1 1 d . . .
H3A H 0.6095 0.2922 0.2506 0.032 Uiso 1 1 calc R . .
H3B H 0.6244 0.1713 0.1310 0.032 Uiso 1 1 calc R . .
C4 C 0.47876(11) 0.29064(19) 0.13489(16) 0.0223(3) Uani 1 1 d . . .
H4A H 0.4618 0.2218 0.0596 0.027 Uiso 1 1 calc R . .
C5 C 0.36870(11) 0.52359(19) 0.06759(16) 0.0228(3) Uani 1 1 d . . .
C6 C 0.35738(13) 0.7097(2) 0.03318(19) 0.0296(4) Uani 1 1 d . . .
H6A H 0.2860 0.7326 0.0093 0.044 Uiso 1 1 calc R . .
H6B H 0.4030 0.7362 -0.0364 0.044 Uiso 1 1 calc R . .
H6C H 0.3757 0.7815 0.1042 0.044 Uiso 1 1 calc R . .
C7 C 0.57259(11) 0.67044(17) 0.22736(18) 0.0224(3) Uani 1 1 d . . .
C8 C 0.67368(14) 0.8846(2) 0.3223(2) 0.0318(4) Uani 1 1 d . . .
H8A H 0.7294 0.9646 0.3024 0.048 Uiso 1 1 calc R . .
H8B H 0.6958 0.8077 0.3888 0.048 Uiso 1 1 calc R . .
H8C H 0.6131 0.9492 0.3492 0.048 Uiso 1 1 calc R . .
C9 C 0.41621(12) 0.22695(17) 0.24401(18) 0.0226(3) Uani 1 1 d . . .
C10 C 0.36214(15) -0.0212(2) 0.3487(2) 0.0389(5) Uani 1 1 d . . .
H10A H 0.3705 -0.1460 0.3463 0.058 Uiso 1 1 calc R . .
H10B H 0.2889 0.0074 0.3436 0.058 Uiso 1 1 calc R . .
H10C H 0.3905 0.0233 0.4263 0.058 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0209(6) 0.0216(6) 0.0215(7) 0.0002(5) 0.0000(6) -0.0021(5)
O1 0.0222(5) 0.0306(5) 0.0315(7) -0.0019(5) -0.0016(5) -0.0021(4)
O2 0.0415(7) 0.0451(7) 0.0236(7) -0.0065(6) 0.0064(7) -0.0191(5)
O3 0.0321(6) 0.0298(5) 0.0290(7) -0.0027(5) 0.0031(6) -0.0117(5)
O4 0.0447(7) 0.0271(5) 0.0252(7) -0.0016(6) 0.0099(6) -0.0006(5)
O5 0.0379(6) 0.0216(5) 0.0389(8) 0.0031(5) 0.0148(7) -0.0003(4)
C1 0.0216(7) 0.0244(7) 0.0221(9) 0.0021(7) 0.0010(7) -0.0034(6)
C2 0.0226(7) 0.0316(8) 0.0281(10) -0.0017(7) 0.0057(7) -0.0004(6)
C3 0.0224(8) 0.0301(8) 0.0283(9) 0.0015(7) 0.0020(7) 0.0045(6)
C4 0.0251(8) 0.0205(7) 0.0214(9) -0.0007(6) 0.0018(7) 0.0000(6)
C5 0.0232(7) 0.0274(7) 0.0180(8) -0.0015(7) 0.0013(7) 0.0002(6)
C6 0.0300(8) 0.0280(8) 0.0309(10) -0.0006(7) -0.0016(8) 0.0028(6)
C7 0.0202(7) 0.0219(6) 0.0252(10) 0.0019(7) -0.0016(7) -0.0016(5)
C8 0.0355(9) 0.0273(8) 0.0326(10) -0.0024(8) -0.0040(9) -0.0086(7)
C9 0.0208(7) 0.0222(7) 0.0246(9) 0.0006(7) -0.0021(7) -0.0008(5)
C10 0.0446(10) 0.0290(8) 0.0432(13) 0.0104(8) 0.0159(10) -0.0020(7)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.354(2) . ?
N1 C1 1.4584(18) . ?
N1 C4 1.4595(19) . ?
O1 C5 1.2273(18) . ?
O2 C7 1.200(2) . ?
O3 C7 1.3357(18) . ?
O3 C8 1.450(2) . ?
O4 C9 1.202(2) . ?
O5 C9 1.3388(18) . ?
O5 C10 1.451(2) . ?
C1 C7 1.517(2) . ?
C1 C2 1.536(2) . ?
C2 C3 1.523(2) . ?
C3 C4 1.543(2) . ?
C4 C9 1.517(2) . ?
C5 C6 1.506(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 126.34(13) . . ?
C5 N1 C4 119.05(12) . . ?
C1 N1 C4 112.98(11) . . ?
C7 O3 C8 115.86(14) . . ?
C9 O5 C10 114.69(14) . . ?
N1 C1 C7 111.85(13) . . ?
N1 C1 C2 102.27(12) . . ?
C7 C1 C2 112.04(13) . . ?
C3 C2 C1 103.08(12) . . ?
C2 C3 C4 103.25(13) . . ?
N1 C4 C9 112.19(12) . . ?
N1 C4 C3 103.45(12) . . ?
C9 C4 C3 111.58(14) . . ?
O1 C5 N1 120.35(14) . . ?
O1 C5 C6 122.52(14) . . ?
N1 C5 C6 117.13(13) . . ?
O2 C7 O3 123.65(16) . . ?
O2 C7 C1 126.19(13) . . ?
O3 C7 C1 110.15(14) . . ?
O4 C9 O5 123.60(16) . . ?
O4 C9 C4 126.84(13) . . ?
O5 C9 C4 109.52(14) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.42
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.033
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_cu-1352
_database_code_depnum_ccdc_archive 'CCDC 1554476'
_audit_update_record             
;
2017-06-06 deposited with the CCDC.
2017-07-24 downloaded from the CCDC.
;

_audit_creation_method           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_chemical_name_systematic        
'Dimethyl (r,r)-1-acetylpyrrolidine-2,5-dicarboxylate'
_chemical_name_common            ?
_chemical_melting_point          370
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H15 N O5'
_chemical_formula_weight         229.23

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   7.8936(2)
_cell_length_b                   13.1800(3)
_cell_length_c                   11.2852(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.484(3)
_cell_angle_gamma                90.00
_cell_volume                     1136.78(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3045
_cell_measurement_theta_min      3.3310
_cell_measurement_theta_max      73.2130

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7053
_exptl_absorpt_correction_T_max  0.8381
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5435
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3980
_diffrn_reflns_av_R_equivalents  0.0117
_diffrn_reflns_av_sigmaI/netI    0.0124
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         5.26
_diffrn_reflns_theta_max         67.50
_reflns_number_total             2054
_reflns_number_gt                1935
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0425P)²+0.4043P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2054
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0873
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.32444(14) 0.57830(8) 0.32450(9) 0.0283(2) Uani 1 1 d . . .
O1 O 0.24739(13) 0.44746(8) 0.19696(8) 0.0395(3) Uani 1 1 d . . .
O2 O 0.03790(14) 0.70195(10) 0.31875(9) 0.0528(3) Uani 1 1 d . . .
O3 O 0.14104(12) 0.74183(7) 0.51594(8) 0.0346(2) Uani 1 1 d . . .
O4 O 0.66374(12) 0.51074(8) 0.31865(8) 0.0381(3) Uani 1 1 d . . .
O5 O 0.60204(12) 0.56412(7) 0.12390(8) 0.0313(2) Uani 1 1 d . . .
C1 C 0.32255(16) 0.64089(10) 0.43042(11) 0.0296(3) Uani 1 1 d . . .
H1A H 0.3450 0.5985 0.5062 0.035 Uiso 1 1 calc R . .
C2 C 0.47575(18) 0.71380(11) 0.43530(13) 0.0362(3) Uani 1 1 d . . .
H2A H 0.4573 0.7790 0.4737 0.043 Uiso 1 1 calc R . .
H2B H 0.5876 0.6837 0.4818 0.043 Uiso 1 1 calc R . .
C3 C 0.47500(19) 0.72868(11) 0.30071(13) 0.0376(3) Uani 1 1 d . . .
H3A H 0.5927 0.7476 0.2921 0.045 Uiso 1 1 calc R . .
H3B H 0.3905 0.7819 0.2624 0.045 Uiso 1 1 calc R . .
C4 C 0.41932(16) 0.62424(10) 0.24290(11) 0.0287(3) Uani 1 1 d . . .
H4A H 0.3395 0.6330 0.1595 0.034 Uiso 1 1 calc R . .
C5 C 0.23661(16) 0.49031(10) 0.29119(11) 0.0293(3) Uani 1 1 d . . .
C6 C 0.12845(18) 0.44899(11) 0.37245(12) 0.0363(3) Uani 1 1 d . . .
H6A H 0.0935 0.3792 0.3482 0.054 Uiso 1 1 calc R . .
H6B H 0.0238 0.4910 0.3644 0.054 Uiso 1 1 calc R . .
H6C H 0.1975 0.4498 0.4577 0.054 Uiso 1 1 calc R . .
C7 C 0.15028(17) 0.69742(10) 0.41232(11) 0.0302(3) Uani 1 1 d . . .
C8 C -0.01369(19) 0.80234(12) 0.51112(13) 0.0391(3) Uani 1 1 d . . .
H8A H -0.0072 0.8314 0.5920 0.059 Uiso 1 1 calc R . .
H8B H -0.1179 0.7594 0.4866 0.059 Uiso 1 1 calc R . .
H8C H -0.0206 0.8571 0.4514 0.059 Uiso 1 1 calc R . .
C9 C 0.57442(16) 0.55886(10) 0.23550(11) 0.0274(3) Uani 1 1 d . . .
C10 C 0.74783(18) 0.50580(12) 0.10516(13) 0.0363(3) Uani 1 1 d . . .
H10A H 0.7516 0.5106 0.0192 0.054 Uiso 1 1 calc R . .
H10B H 0.7339 0.4346 0.1260 0.054 Uiso 1 1 calc R . .
H10C H 0.8570 0.5325 0.1575 0.054 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0320(6) 0.0295(6) 0.0237(5) -0.0033(4) 0.0076(4) -0.0005(4)
O1 0.0482(6) 0.0393(6) 0.0308(5) -0.0092(4) 0.0094(4) -0.0086(4)
O2 0.0485(6) 0.0726(8) 0.0291(5) -0.0101(5) -0.0059(5) 0.0254(6)
O3 0.0330(5) 0.0437(5) 0.0246(5) -0.0051(4) 0.0026(4) 0.0115(4)
O4 0.0354(5) 0.0516(6) 0.0264(5) 0.0100(4) 0.0064(4) 0.0100(4)
O5 0.0326(5) 0.0389(5) 0.0227(4) 0.0031(4) 0.0075(4) 0.0027(4)
C1 0.0316(7) 0.0330(7) 0.0222(6) -0.0035(5) 0.0031(5) 0.0039(5)
C2 0.0321(7) 0.0367(7) 0.0367(7) -0.0097(6) 0.0026(6) 0.0007(6)
C3 0.0400(7) 0.0306(7) 0.0427(8) -0.0013(6) 0.0111(6) -0.0016(6)
C4 0.0301(6) 0.0310(7) 0.0239(6) 0.0021(5) 0.0049(5) 0.0010(5)
C5 0.0277(6) 0.0324(7) 0.0250(6) 0.0009(5) 0.0012(5) 0.0012(5)
C6 0.0322(7) 0.0433(8) 0.0315(7) 0.0048(6) 0.0042(5) -0.0036(6)
C7 0.0329(7) 0.0335(7) 0.0221(6) -0.0016(5) 0.0027(5) 0.0027(5)
C8 0.0360(7) 0.0479(8) 0.0335(7) 0.0005(6) 0.0088(6) 0.0152(6)
C9 0.0284(6) 0.0304(6) 0.0224(6) 0.0005(5) 0.0042(5) -0.0034(5)
C10 0.0337(7) 0.0446(8) 0.0334(7) 0.0004(6) 0.0136(6) 0.0007(6)

_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 1.3552(17) . ?
N1 C1 1.4555(16) . ?
N1 C4 1.4562(16) . ?
O1 C5 1.2257(16) . ?
O2 C7 1.1987(16) . ?
O3 C7 1.3259(15) . ?
O3 C8 1.4483(16) . ?
O4 C9 1.2036(16) . ?
O5 C9 1.3327(15) . ?
O5 C10 1.4428(16) . ?
C1 C7 1.5189(17) . ?
C1 C2 1.5348(19) . ?
C2 C3 1.530(2) . ?
C3 C4 1.5395(19) . ?
C4 C9 1.5164(17) . ?
C5 C6 1.5026(19) . ?

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 C1 127.10(11) . . ?
C5 N1 C4 119.26(10) . . ?
C1 N1 C4 113.34(10) . . ?
C7 O3 C8 116.22(10) . . ?
C9 O5 C10 115.84(10) . . ?
N1 C1 C7 111.12(10) . . ?
N1 C1 C2 102.39(10) . . ?
C7 C1 C2 111.63(11) . . ?
C3 C2 C1 103.72(10) . . ?
C2 C3 C4 103.65(11) . . ?
N1 C4 C9 110.39(10) . . ?
N1 C4 C3 103.96(10) . . ?
C9 C4 C3 112.49(10) . . ?
O1 C5 N1 119.55(12) . . ?
O1 C5 C6 122.40(12) . . ?
N1 C5 C6 118.05(11) . . ?
O2 C7 O3 124.27(12) . . ?
O2 C7 C1 125.68(12) . . ?
O3 C7 C1 110.05(10) . . ?
O4 C9 O5 124.18(12) . . ?
O4 C9 C4 125.46(11) . . ?
O5 C9 C4 110.34(10) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.043
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
