# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_ed082
_database_code_depnum_ccdc_archive 'CCDC 957613'
_audit_update_record             
;
2013-08-27 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;

_audit_creation_date             2013-08-10T08:03:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 dimethyl (3S,5S)-3-(2,6-dimethoxyphenyl)-5-methylpyrrolidine-
2,2-dicarboxylate
;
_chemical_formula_moiety         'C17 H23 N1 O6'
_chemical_formula_sum            'C17 H23 N O6'
_chemical_formula_weight         337.36
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.22300(10)
_cell_length_b                   7.16940(10)
_cell_length_c                   13.32590(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.7310(10)
_cell_angle_gamma                90
_cell_volume                     880.153(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13321
_cell_measurement_theta_min      3.3175
_cell_measurement_theta_max      73.9279
_cell_measurement_wavelength     1.54184

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4512
_exptl_crystal_size_mid          0.3172
_exptl_crystal_size_min          0.0558
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 -2 1 0.1151
3 -3 -4 0.1363
0 4 3 0.0991
3 4 1 0.1442
0 -1 9 0.023
0 1 -9 0.0328

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_correction_T_min  0.803
_exptl_absorpt_correction_T_max  0.957

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Nova (Cu) X-ray micro-source'
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_source_voltage           50
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 10.4023
_diffrn_orient_matrix_ub_11      0.0926327
_diffrn_orient_matrix_ub_12      -0.1118374
_diffrn_orient_matrix_ub_13      0.0781345
_diffrn_orient_matrix_ub_21      -0.1003751
_diffrn_orient_matrix_ub_22      0.0625114
_diffrn_orient_matrix_ub_23      0.0828305
_diffrn_orient_matrix_ub_31      -0.0964686
_diffrn_orient_matrix_ub_32      -0.1725328
_diffrn_orient_matrix_ub_33      -0.0206799
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_number            17228
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         72.39
_diffrn_reflns_theta_full        72.39
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             3470
_reflns_number_gt                3416
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -91.00  -65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7631  125.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -60.00  -20.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7631  -38.0000  -60.0000 40

#__ type_ start__ end____ width___ exp.time_
  3 omega  -26.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7631  -38.0000   90.0000 93

#__ type_ start__ end____ width___ exp.time_
  4 omega   12.00  108.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7631   57.0000   30.0000 96

#__ type_ start__ end____ width___ exp.time_
  5 omega  -33.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7631  -57.0000 -120.0000 99

#__ type_ start__ end____ width___ exp.time_
  6 omega  -40.00  -15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   30.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega  -86.00  -60.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -45.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega  -80.00  -50.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
  9 omega   39.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -49.0000  -44.0000 40

#__ type_ start__ end____ width___ exp.time_
 10 omega   80.00  113.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000    0.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   36.00   70.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000   90.0000 34

#__ type_ start__ end____ width___ exp.time_
 12 omega  122.00  156.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
 13 omega   79.00  136.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   30.0000   60.0000 57

#__ type_ start__ end____ width___ exp.time_
 14 omega   33.00   68.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  120.0000 35

#__ type_ start__ end____ width___ exp.time_
 15 omega   30.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000 -150.0000 35

#__ type_ start__ end____ width___ exp.time_
 16 omega   81.00  125.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000    0.0000 44

#__ type_ start__ end____ width___ exp.time_
 17 omega   31.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
 18 omega  114.00  147.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000  -60.0000 33

#__ type_ start__ end____ width___ exp.time_
 19 omega   75.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000  -60.0000 32

#__ type_ start__ end____ width___ exp.time_
 20 omega   30.00   55.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 21 omega   76.00  136.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000  -90.0000 60

#__ type_ start__ end____ width___ exp.time_
 22 omega   35.00  121.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000  150.0000 86

#__ type_ start__ end____ width___ exp.time_
 23 omega   88.00  128.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000   90.0000 40

#__ type_ start__ end____ width___ exp.time_
 24 omega  131.00  157.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   35.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -49.0000 -103.0000 47

#__ type_ start__ end____ width___ exp.time_
 26 omega   84.00  151.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000 -180.0000 67

#__ type_ start__ end____ width___ exp.time_
 27 omega   36.00   62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7631 -125.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 28 omega   41.00   71.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000    0.0000 30

#__ type_ start__ end____ width___ exp.time_
 29 omega   64.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000    0.0000 38

#__ type_ start__ end____ width___ exp.time_
 30 omega   64.00  121.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000 -150.0000 57

#__ type_ start__ end____ width___ exp.time_
 31 omega   59.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 32 omega   68.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000  -90.0000 34

#__ type_ start__ end____ width___ exp.time_
 33 omega   55.00   84.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000 -120.0000 29

#__ type_ start__ end____ width___ exp.time_
 34 omega  124.00  156.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  125.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
 35 omega  -74.00   38.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7631   77.0000   60.0000 112

#__ type_ start__ end____ width___ exp.time_
 36 omega -119.00   -7.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7631  -77.0000   30.0000 112

#__ type_ start__ end____ width___ exp.time_
 37 omega  -70.00   33.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7631   57.0000   30.0000 103

#__ type_ start__ end____ width___ exp.time_
 38 omega -119.00   -7.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7631  -77.0000  -90.0000 112

#__ type_ start__ end____ width___ exp.time_
 39 omega    7.00  119.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7631   77.0000  120.0000 112

#__ type_ start__ end____ width___ exp.time_
 40 omega   11.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7631   57.0000 -150.0000 104

#__ type_ start__ end____ width___ exp.time_
 41 omega    7.00  119.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7631   77.0000 -120.0000 112

#__ type_ start__ end____ width___ exp.time_
 42 omega -157.00  -85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -61.0000    0.0000 72

#__ type_ start__ end____ width___ exp.time_
 43 omega -162.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -150.0000 113

#__ type_ start__ end____ width___ exp.time_
 44 omega -162.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   60.0000 113

#__ type_ start__ end____ width___ exp.time_
 45 omega -162.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  150.0000 113

#__ type_ start__ end____ width___ exp.time_
 46 omega -162.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -120.0000 113

#__ type_ start__ end____ width___ exp.time_
 47 omega -157.00  -53.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -61.0000   90.0000 104

#__ type_ start__ end____ width___ exp.time_
 48 omega   75.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000 -120.0000 83

#__ type_ start__ end____ width___ exp.time_
 49 omega   24.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000 -180.0000 85

#__ type_ start__ end____ width___ exp.time_
 50 omega   78.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000  120.0000 80

#__ type_ start__ end____ width___ exp.time_
 51 omega   24.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000  -30.0000 85

#__ type_ start__ end____ width___ exp.time_
 52 omega   75.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000 -150.0000 83

;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_structure_solution    'OLEX2 (Dolomanov et al, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond v.3.2f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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)+(0.0565P)²+0.0828P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3470
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0775
_refine_ls_wR_factor_gt          0.0769
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
The Friedel pair coverage of the experiment is almost complete (98%).
Analysis of the absolute structure using likelihood methods
(Hooft, Straver & Spek, 2008) was performed using PLATON (Spek, 2011).
 The results indicated that the absolute structure had been correctly
 assigned. The method calculated that the probability that the structure 
is inverted is smaller than 10-99. The absolute structure parameter y 
(Hooft, Straver & Spek, 2008) was calculated using PLATON (Spek,
2010). The resulting value was y=0.08(4), which together with Flack parameter 
value, indicate that the absolute structure has sureley been determined 
correctly.

Flack, H. D. (1983), Acta Cryst. A39, 876-881
Flack & G. Bernardinelli, Acta Cryst. 1999, A55, 908-915; 
H. D. Flack & G. Bernardinelli, J. Appl. Cryst. 2000, 33, 1143-1148.

R. W. W. Hooft, L. H. Straver & A. L. Spek, J. Appl. Cryst. 2008, 41, 96-103
A. L. Spek (2010) PLATON, Utrecht, The Netherlands; 
A. L. Spek, J. Appl. Cryst. 2003, 36, 7-13
A. L. Thompson & D. J. Watkin, Tetrahedron: Asymmetry 2009, 20, 712--717

;
_refine_ls_abs_structure_Flack   0.03(11)
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.19
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'

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
C2 C 0.75292(11) 1.02622(17) 0.31352(8) 0.0157(2) Uani 1 1 d . . .
C3 C 0.62292(11) 1.13717(17) 0.25973(8) 0.0162(2) Uani 1 1 d . . .
H3 H 0.5792 1.2188 0.3111 0.019 Uiso 1 1 calc R . .
C4 C 0.69945(13) 1.26481(18) 0.18488(9) 0.0207(2) Uani 1 1 d . . .
H4A H 0.6725 1.229 0.1147 0.025 Uiso 1 1 calc R . .
H4B H 0.6725 1.3969 0.1949 0.025 Uiso 1 1 calc R . .
C5 C 0.86309(13) 1.23568(19) 0.20792(9) 0.0239(3) Uani 1 1 d . . .
H5 H 0.8965 1.3294 0.2596 0.029 Uiso 1 1 calc R . .
C6 C 0.79387(11) 1.11297(16) 0.41692(8) 0.0156(2) Uani 1 1 d . . .
C7 C 0.94236(13) 1.08135(19) 0.56479(9) 0.0227(3) Uani 1 1 d . . .
H7A H 0.9778 1.209 0.5564 0.034 Uiso 1 1 calc R . .
H7B H 1.0214 1.0029 0.5927 0.034 Uiso 1 1 calc R . .
H7C H 0.8624 1.0817 0.6107 0.034 Uiso 1 1 calc R . .
C8 C 0.71511(12) 0.82199(17) 0.32830(8) 0.0172(2) Uani 1 1 d . . .
C9 C 0.54188(14) 0.62892(19) 0.40309(11) 0.0278(3) Uani 1 1 d . . .
H9A H 0.4803 0.6059 0.3424 0.042 Uiso 1 1 calc R . .
H9B H 0.4821 0.6278 0.4619 0.042 Uiso 1 1 calc R . .
H9C H 0.616 0.5312 0.4102 0.042 Uiso 1 1 calc R . .
C10 C 0.50339(12) 1.01387(17) 0.21411(8) 0.0164(2) Uani 1 1 d . . .
C11 C 0.36570(12) 1.01556(18) 0.25506(8) 0.0182(2) Uani 1 1 d . . .
C12 C 0.25409(13) 0.89726(19) 0.21955(9) 0.0235(3) Uani 1 1 d . . .
H12 H 0.1613 0.9015 0.2475 0.028 Uiso 1 1 calc R . .
C13 C 0.28173(14) 0.7737(2) 0.14274(9) 0.0263(3) Uani 1 1 d . . .
H13 H 0.2072 0.691 0.1192 0.032 Uiso 1 1 calc R . .
C14 C 0.41526(14) 0.76764(19) 0.09954(9) 0.0240(3) Uani 1 1 d . . .
H14 H 0.4321 0.6825 0.0468 0.029 Uiso 1 1 calc R . .
C15 C 0.52438(13) 0.88850(18) 0.13476(8) 0.0189(2) Uani 1 1 d . . .
C16 C 0.21780(13) 1.1303(2) 0.38373(9) 0.0246(3) Uani 1 1 d . . .
H16A H 0.1348 1.1558 0.337 0.037 Uiso 1 1 calc R . .
H16B H 0.2207 1.2231 0.4378 0.037 Uiso 1 1 calc R . .
H16C H 0.2078 1.0054 0.4125 0.037 Uiso 1 1 calc R . .
C17 C 0.69312(16) 0.7539(2) 0.02414(10) 0.0335(3) Uani 1 1 d . . .
H17A H 0.6312 0.7702 -0.0371 0.05 Uiso 1 1 calc R . .
H17B H 0.6762 0.6302 0.0527 0.05 Uiso 1 1 calc R . .
H17C H 0.7952 0.7652 0.0078 0.05 Uiso 1 1 calc R . .
C18 C 0.95632(15) 1.2563(3) 0.11765(11) 0.0422(4) Uani 1 1 d . . .
H18A H 0.9259 1.1646 0.0663 0.063 Uiso 1 1 calc R . .
H18B H 1.0584 1.2352 0.1384 0.063 Uiso 1 1 calc R . .
H18C H 0.9449 1.3823 0.0899 0.063 Uiso 1 1 calc R . .
N1 N 0.87984(10) 1.04748(16) 0.25255(7) 0.0204(2) Uani 1 1 d . . .
O1 O 0.74951(10) 1.25837(13) 0.44702(6) 0.0279(2) Uani 1 1 d . . .
O2 O 0.89108(9) 1.00770(12) 0.46777(6) 0.02074(18) Uani 1 1 d . . .
O3 O 0.76610(10) 0.69364(12) 0.28405(7) 0.0250(2) Uani 1 1 d . . .
O4 O 0.61181(9) 0.80915(12) 0.39535(6) 0.01932(18) Uani 1 1 d . . .
O5 O 0.34897(9) 1.13994(13) 0.33113(6) 0.02229(19) Uani 1 1 d . . .
O6 O 0.65917(9) 0.89372(12) 0.09544(6) 0.02238(19) Uani 1 1 d . . .
H1 H 0.8676(18) 0.959(3) 0.2037(13) 0.026(4) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C2 N1 1.4643(13) . ?
C2 C8 1.5201(17) . ?
C2 C6 1.5423(15) . ?
C2 C3 1.5818(15) . ?
C3 C10 1.5173(15) . ?
C3 C4 1.5485(16) . ?
C3 H3 1 . ?
C4 C5 1.5400(17) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 N1 1.4797(17) . ?
C5 C18 1.5189(17) . ?
C5 H5 1 . ?
C6 O1 1.1961(15) . ?
C6 O2 1.3322(14) . ?
C7 O2 1.4546(14) . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 O3 1.2009(15) . ?
C8 O4 1.3400(14) . ?
C9 O4 1.4501(15) . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 C11 1.4060(15) . ?
C10 C15 1.4082(16) . ?
C11 O5 1.3644(15) . ?
C11 C12 1.3988(16) . ?
C12 C13 1.3866(19) . ?
C12 H12 0.95 . ?
C13 C14 1.3848(18) . ?
C13 H13 0.95 . ?
C14 C15 1.3924(18) . ?
C14 H14 0.95 . ?
C15 O6 1.3724(14) . ?
C16 O5 1.4285(14) . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 O6 1.4262(16) . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
N1 H1 0.913(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C2 C8 111.50(9) . . ?
N1 C2 C6 106.59(9) . . ?
C8 C2 C6 108.70(9) . . ?
N1 C2 C3 107.76(9) . . ?
C8 C2 C3 111.68(9) . . ?
C6 C2 C3 110.50(9) . . ?
C10 C3 C4 115.53(9) . . ?
C10 C3 C2 114.15(9) . . ?
C4 C3 C2 103.30(9) . . ?
C10 C3 H3 107.8 . . ?
C4 C3 H3 107.8 . . ?
C2 C3 H3 107.8 . . ?
C5 C4 C3 105.30(9) . . ?
C5 C4 H4A 110.7 . . ?
C3 C4 H4A 110.7 . . ?
C5 C4 H4B 110.7 . . ?
C3 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
N1 C5 C18 110.78(12) . . ?
N1 C5 C4 106.64(10) . . ?
C18 C5 C4 114.54(10) . . ?
N1 C5 H5 108.2 . . ?
C18 C5 H5 108.2 . . ?
C4 C5 H5 108.2 . . ?
O1 C6 O2 123.77(10) . . ?
O1 C6 C2 125.30(10) . . ?
O2 C6 C2 110.87(9) . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O3 C8 O4 125.61(11) . . ?
O3 C8 C2 125.23(11) . . ?
O4 C8 C2 109.11(9) . . ?
O4 C9 H9A 109.5 . . ?
O4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 117.13(10) . . ?
C11 C10 C3 119.47(10) . . ?
C15 C10 C3 123.33(10) . . ?
O5 C11 C12 122.70(10) . . ?
O5 C11 C10 115.48(10) . . ?
C12 C11 C10 121.82(10) . . ?
C13 C12 C11 118.62(11) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C14 C13 C12 121.69(11) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 118.90(11) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.6 . . ?
O6 C15 C14 122.79(10) . . ?
O6 C15 C10 115.38(10) . . ?
C14 C15 C10 121.82(11) . . ?
O5 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O6 C17 H17A 109.5 . . ?
O6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C5 C18 H18A 109.5 . . ?
C5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 N1 C5 104.30(9) . . ?
C2 N1 H1 104.4(11) . . ?
C5 N1 H1 109.9(10) . . ?
C6 O2 C7 115.40(9) . . ?
C8 O4 C9 116.20(10) . . ?
C11 O5 C16 117.47(9) . . ?
C15 O6 C17 117.82(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C10 110.08(10) . . . . ?
C8 C2 C3 C10 -12.71(13) . . . . ?
C6 C2 C3 C10 -133.84(10) . . . . ?
N1 C2 C3 C4 -16.18(11) . . . . ?
C8 C2 C3 C4 -138.96(9) . . . . ?
C6 C2 C3 C4 99.91(10) . . . . ?
C10 C3 C4 C5 -131.22(10) . . . . ?
C2 C3 C4 C5 -5.86(11) . . . . ?
C3 C4 C5 N1 25.90(12) . . . . ?
C3 C4 C5 C18 148.82(12) . . . . ?
N1 C2 C6 O1 106.77(13) . . . . ?
C8 C2 C6 O1 -132.93(12) . . . . ?
C3 C2 C6 O1 -10.05(16) . . . . ?
N1 C2 C6 O2 -70.63(11) . . . . ?
C8 C2 C6 O2 49.67(12) . . . . ?
C3 C2 C6 O2 172.55(9) . . . . ?
N1 C2 C8 O3 -10.93(15) . . . . ?
C6 C2 C8 O3 -128.14(11) . . . . ?
C3 C2 C8 O3 109.69(12) . . . . ?
N1 C2 C8 O4 171.59(8) . . . . ?
C6 C2 C8 O4 54.38(11) . . . . ?
C3 C2 C8 O4 -67.79(11) . . . . ?
C4 C3 C10 C11 -127.74(11) . . . . ?
C2 C3 C10 C11 112.68(11) . . . . ?
C4 C3 C10 C15 55.55(15) . . . . ?
C2 C3 C10 C15 -64.03(14) . . . . ?
C15 C10 C11 O5 -179.42(10) . . . . ?
C3 C10 C11 O5 3.67(15) . . . . ?
C15 C10 C11 C12 0.51(16) . . . . ?
C3 C10 C11 C12 -176.41(11) . . . . ?
O5 C11 C12 C13 -179.20(11) . . . . ?
C10 C11 C12 C13 0.89(18) . . . . ?
C11 C12 C13 C14 -1.31(19) . . . . ?
C12 C13 C14 C15 0.31(19) . . . . ?
C13 C14 C15 O6 -179.11(11) . . . . ?
C13 C14 C15 C10 1.17(18) . . . . ?
C11 C10 C15 O6 178.71(9) . . . . ?
C3 C10 C15 O6 -4.51(16) . . . . ?
C11 C10 C15 C14 -1.55(16) . . . . ?
C3 C10 C15 C14 175.23(11) . . . . ?
C8 C2 N1 C5 155.39(9) . . . . ?
C6 C2 N1 C5 -86.13(10) . . . . ?
C3 C2 N1 C5 32.49(11) . . . . ?
C18 C5 N1 C2 -161.59(10) . . . . ?
C4 C5 N1 C2 -36.35(11) . . . . ?
O1 C6 O2 C7 -0.15(16) . . . . ?
C2 C6 O2 C7 177.30(9) . . . . ?
O3 C8 O4 C9 -9.71(16) . . . . ?
C2 C8 O4 C9 167.76(9) . . . . ?
C12 C11 O5 C16 7.97(16) . . . . ?
C10 C11 O5 C16 -172.11(10) . . . . ?
C14 C15 O6 C17 -7.75(16) . . . . ?
C10 C15 O6 C17 171.99(11) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
