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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mo_dm11166_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H25 N O3'
_chemical_formula_weight         279.37

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   7.2984(19)
_cell_length_b                   10.981(3)
_cell_length_c                   10.041(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.375(4)
_cell_angle_gamma                90.00
_cell_volume                     804.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    2548
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      30.61

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9654
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5782
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3346
_reflns_number_gt                3236
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of 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)+(0.0653P)²+0.0426P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.2(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3346
_refine_ls_number_parameters     185
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0916
_refine_ls_wR_factor_gt          0.0901
_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 0.81216(14) 0.17692(9) 0.32491(10) 0.0209(2) Uani 1 1 d . . .
O1 O 0.64816(14) 0.31429(9) 0.19132(10) 0.0322(2) Uani 1 1 d . . .
O2 O 0.74223(15) 0.36277(9) 0.39707(10) 0.0343(2) Uani 1 1 d . . .
O3 O 0.91099(13) -0.01437(8) 0.29714(9) 0.0279(2) Uani 1 1 d . . .
C1 C 0.92854(17) 0.19263(13) 0.44433(11) 0.0240(3) Uani 1 1 d . . .
H1 H 0.9184 0.1194 0.5030 0.029 Uiso 1 1 calc R . .
C2 C 0.83076(19) 0.30032(14) 0.50806(14) 0.0324(3) Uani 1 1 d . . .
H2A H 0.7390 0.2721 0.5734 0.039 Uiso 1 1 calc R . .
H2B H 0.9193 0.3546 0.5537 0.039 Uiso 1 1 calc R . .
C3 C 0.72519(17) 0.28623(12) 0.29256(13) 0.0256(3) Uani 1 1 d . . .
C4 C 0.81411(16) 0.06718(11) 0.25507(11) 0.0199(2) Uani 1 1 d . . .
C5 C 0.69445(15) 0.05417(10) 0.13351(11) 0.0192(2) Uani 1 1 d . . .
C6 C 0.77638(16) 0.09979(11) 0.00305(12) 0.0217(2) Uani 1 1 d . . .
C7 C 0.76217(18) -0.03490(11) 0.03022(12) 0.0238(3) Uani 1 1 d . . .
H7A H 0.8769 -0.0797 0.0499 0.029 Uiso 1 1 calc R . .
H7B H 0.6693 -0.0818 -0.0206 0.029 Uiso 1 1 calc R . .
C8 C 0.48926(16) 0.05756(12) 0.15855(13) 0.0244(3) Uani 1 1 d . . .
H8A H 0.4231 0.0403 0.0743 0.029 Uiso 1 1 calc R . .
H8B H 0.4541 0.1402 0.1883 0.029 Uiso 1 1 calc R . .
C9 C 0.4322(2) -0.03468(13) 0.26338(14) 0.0315(3) Uani 1 1 d . . .
H9A H 0.4775 -0.0085 0.3509 0.047 Uiso 1 1 calc R . .
H9B H 0.4842 -0.1145 0.2416 0.047 Uiso 1 1 calc R . .
H9C H 0.2983 -0.0405 0.2652 0.047 Uiso 1 1 calc R . .
C10 C 0.96631(18) 0.15656(14) 0.00812(13) 0.0282(3) Uani 1 1 d . . .
H10A H 1.0393 0.1166 0.0791 0.034 Uiso 1 1 calc R . .
H10B H 0.9551 0.2439 0.0310 0.034 Uiso 1 1 calc R . .
C11 C 1.0665(2) 0.14430(19) -0.12390(16) 0.0454(4) Uani 1 1 d . . .
H11A H 0.9977 0.1871 -0.1937 0.068 Uiso 1 1 calc R . .
H11B H 1.0770 0.0580 -0.1473 0.068 Uiso 1 1 calc R . .
H11C H 1.1891 0.1799 -0.1155 0.068 Uiso 1 1 calc R . .
C12 C 0.65140(18) 0.16077(13) -0.09376(12) 0.0276(3) Uani 1 1 d . . .
H12 H 0.6341 0.2459 -0.0829 0.033 Uiso 1 1 calc R . .
C13 C 0.5624(2) 0.10870(15) -0.19285(14) 0.0330(3) Uani 1 1 d . . .
H13A H 0.5751 0.0237 -0.2080 0.040 Uiso 1 1 calc R . .
H13B H 0.4856 0.1561 -0.2493 0.040 Uiso 1 1 calc R . .
C14 C 1.12956(17) 0.21414(12) 0.40769(12) 0.0240(3) Uani 1 1 d . . .
H14 H 1.1670 0.1466 0.3469 0.029 Uiso 1 1 calc R . .
C15 C 1.1622(2) 0.33374(14) 0.33394(14) 0.0328(3) Uani 1 1 d . . .
H15A H 1.2914 0.3393 0.3086 0.049 Uiso 1 1 calc R . .
H15B H 1.1313 0.4022 0.3922 0.049 Uiso 1 1 calc R . .
H15C H 1.0850 0.3364 0.2538 0.049 Uiso 1 1 calc R . .
C16 C 1.2499(2) 0.20563(16) 0.53262(14) 0.0342(3) Uani 1 1 d . . .
H16A H 1.2175 0.2713 0.5942 0.051 Uiso 1 1 calc R . .
H16B H 1.3790 0.2133 0.5077 0.051 Uiso 1 1 calc R . .
H16C H 1.2302 0.1268 0.5760 0.051 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.3944(16) . ?
N1 C3 1.3952(16) . ?
N1 C1 1.4751(15) . ?
O1 C3 1.1988(17) . ?
O2 C3 1.3496(16) . ?
O2 C2 1.4561(19) . ?
O3 C4 1.2151(16) . ?
C1 C2 1.5243(19) . ?
C1 C14 1.5332(18) . ?
C1 H1 1.0000 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C4 C5 1.5030(16) . ?
C5 C7 1.5111(16) . ?
C5 C8 1.5206(16) . ?
C5 C6 1.5280(16) . ?
C6 C12 1.4879(17) . ?
C6 C7 1.5077(17) . ?
C6 C10 1.5205(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5209(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.5240(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.315(2) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9500 . ?
C13 H13B 0.9500 . ?
C14 C15 1.5273(19) . ?
C14 C16 1.5293(17) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 C3 129.24(10) . . ?
C4 N1 C1 120.15(10) . . ?
C3 N1 C1 110.32(10) . . ?
C3 O2 C2 109.88(11) . . ?
N1 C1 C2 99.40(10) . . ?
N1 C1 C14 111.70(10) . . ?
C2 C1 C14 115.63(11) . . ?
N1 C1 H1 109.9 . . ?
C2 C1 H1 109.9 . . ?
C14 C1 H1 109.9 . . ?
O2 C2 C1 104.52(10) . . ?
O2 C2 H2A 110.8 . . ?
C1 C2 H2A 110.8 . . ?
O2 C2 H2B 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
O1 C3 O2 122.66(12) . . ?
O1 C3 N1 128.96(12) . . ?
O2 C3 N1 108.38(11) . . ?
O3 C4 N1 118.03(11) . . ?
O3 C4 C5 123.09(11) . . ?
N1 C4 C5 118.87(10) . . ?
C4 C5 C7 115.34(10) . . ?
C4 C5 C8 115.53(9) . . ?
C7 C5 C8 117.15(10) . . ?
C4 C5 C6 115.88(9) . . ?
C7 C5 C6 59.48(8) . . ?
C8 C5 C6 121.67(10) . . ?
C12 C6 C7 121.14(11) . . ?
C12 C6 C10 113.09(11) . . ?
C7 C6 C10 117.38(11) . . ?
C12 C6 C5 117.78(10) . . ?
C7 C6 C5 59.70(8) . . ?
C10 C6 C5 117.87(10) . . ?
C6 C7 C5 60.82(8) . . ?
C6 C7 H7A 117.7 . . ?
C5 C7 H7A 117.7 . . ?
C6 C7 H7B 117.7 . . ?
C5 C7 H7B 117.7 . . ?
H7A C7 H7B 114.8 . . ?
C5 C8 C9 111.86(11) . . ?
C5 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C5 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 C11 112.15(12) . . ?
C6 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C6 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
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 . . ?
C13 C12 C6 126.59(13) . . ?
C13 C12 H12 116.7 . . ?
C6 C12 H12 116.7 . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
C15 C14 C16 111.08(11) . . ?
C15 C14 C1 113.67(11) . . ?
C16 C14 C1 109.81(10) . . ?
C15 C14 H14 107.3 . . ?
C16 C14 H14 107.3 . . ?
C1 C14 H14 107.3 . . ?
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 . . ?

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
C4 N1 C1 C2 -160.86(11) . . . . ?
C3 N1 C1 C2 24.77(12) . . . . ?
C4 N1 C1 C14 76.60(14) . . . . ?
C3 N1 C1 C14 -97.77(12) . . . . ?
C3 O2 C2 C1 20.30(14) . . . . ?
N1 C1 C2 O2 -26.01(12) . . . . ?
C14 C1 C2 O2 93.67(12) . . . . ?
C2 O2 C3 O1 176.12(13) . . . . ?
C2 O2 C3 N1 -4.68(14) . . . . ?
C4 N1 C3 O1 -8.4(2) . . . . ?
C1 N1 C3 O1 165.30(13) . . . . ?
C4 N1 C3 O2 172.46(11) . . . . ?
C1 N1 C3 O2 -13.83(13) . . . . ?
C3 N1 C4 O3 174.56(11) . . . . ?
C1 N1 C4 O3 1.38(17) . . . . ?
C3 N1 C4 C5 -6.62(18) . . . . ?
C1 N1 C4 C5 -179.79(10) . . . . ?
O3 C4 C5 C7 -28.68(16) . . . . ?
N1 C4 C5 C7 152.56(11) . . . . ?
O3 C4 C5 C8 113.11(13) . . . . ?
N1 C4 C5 C8 -65.65(14) . . . . ?
O3 C4 C5 C6 -95.43(14) . . . . ?
N1 C4 C5 C6 85.81(13) . . . . ?
C4 C5 C6 C12 -142.89(11) . . . . ?
C7 C5 C6 C12 111.67(13) . . . . ?
C8 C5 C6 C12 6.68(16) . . . . ?
C4 C5 C6 C7 105.44(11) . . . . ?
C8 C5 C6 C7 -104.99(12) . . . . ?
C4 C5 C6 C10 -1.63(16) . . . . ?
C7 C5 C6 C10 -107.07(13) . . . . ?
C8 C5 C6 C10 147.94(11) . . . . ?
C12 C6 C7 C5 -106.12(13) . . . . ?
C10 C6 C7 C5 107.88(12) . . . . ?
C4 C5 C7 C6 -106.35(11) . . . . ?
C8 C5 C7 C6 112.50(12) . . . . ?
C4 C5 C8 C9 -53.42(14) . . . . ?
C7 C5 C8 C9 87.66(13) . . . . ?
C6 C5 C8 C9 156.91(11) . . . . ?
C12 C6 C10 C11 -63.44(17) . . . . ?
C7 C6 C10 C11 85.21(16) . . . . ?
C5 C6 C10 C11 153.57(13) . . . . ?
C7 C6 C12 C13 -23.1(2) . . . . ?
C10 C6 C12 C13 124.20(15) . . . . ?
C5 C6 C12 C13 -92.76(16) . . . . ?
N1 C1 C14 C15 65.62(14) . . . . ?
C2 C1 C14 C15 -47.08(15) . . . . ?
N1 C1 C14 C16 -169.25(11) . . . . ?
C2 C1 C14 C16 78.04(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.041
_database_code_depnum_ccdc_archive 'CCDC 978791'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cd212214

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H21 N O5'
_chemical_formula_weight         283.32

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

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

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

_cell_length_a                   5.510(5)
_cell_length_b                   13.604(11)
_cell_length_c                   19.941(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1495(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3264
_cell_measurement_theta_min      5.050
_cell_measurement_theta_max      47.967

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.112
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.72622
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9047
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2942
_reflns_number_gt                2536
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of 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)+(0.0602P)²+0.0872P] 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   -0.1(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2942
_refine_ls_number_parameters     204
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1050
_refine_ls_wR_factor_gt          0.1004
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.031
_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 0.8489(3) 1.07644(10) 0.00966(7) 0.0490(4) Uani 1 1 d . . .
O1 O 0.5977(3) 1.14453(11) 0.09080(8) 0.0752(4) Uani 1 1 d . . .
O2 O 0.5746(3) 1.19084(10) -0.01576(8) 0.0701(4) Uani 1 1 d . . .
O3 O 1.2048(2) 0.99821(11) 0.02006(6) 0.0648(4) Uani 1 1 d . . .
O4 O 1.0070(3) 0.82322(10) 0.09978(7) 0.0656(4) Uani 1 1 d . A .
O5 O 1.1159(2) 0.90712(10) 0.13361(7) 0.0637(4) Uani 1 1 d . . .
C1 C 0.6678(4) 1.13724(13) 0.03443(12) 0.0583(5) Uani 1 1 d . . .
C2 C 0.6981(4) 1.17062(15) -0.07689(11) 0.0678(6) Uani 1 1 d . . .
H2A H 0.7684 1.2304 -0.0949 0.081 Uiso 1 1 calc R . .
H2B H 0.5859 1.1441 -0.1097 0.081 Uiso 1 1 calc R . .
C3 C 0.8962(4) 1.09628(13) -0.06165(9) 0.0540(4) Uani 1 1 d . . .
H3 H 1.0548 1.1282 -0.0662 0.065 Uiso 1 1 calc R . .
C4 C 0.8912(4) 1.00397(15) -0.10520(9) 0.0603(5) Uani 1 1 d . . .
H4 H 1.0158 0.9592 -0.0879 0.072 Uiso 1 1 calc R . .
C5 C 0.6506(5) 0.95009(17) -0.10229(13) 0.0838(7) Uani 1 1 d . . .
H5A H 0.6062 0.9392 -0.0563 0.126 Uiso 1 1 calc R . .
H5B H 0.6653 0.8880 -0.1248 0.126 Uiso 1 1 calc R . .
H5C H 0.5278 0.9889 -0.1239 0.126 Uiso 1 1 calc R . .
C6 C 0.9605(6) 1.0301(2) -0.17650(12) 0.0929(8) Uani 1 1 d . . .
H6A H 0.9733 0.9712 -0.2027 0.139 Uiso 1 1 calc R . .
H6B H 1.1138 1.0637 -0.1765 0.139 Uiso 1 1 calc R . .
H6C H 0.8385 1.0721 -0.1955 0.139 Uiso 1 1 calc R . .
C7 C 1.0160(3) 1.02022(13) 0.04638(9) 0.0478(4) Uani 1 1 d . . .
C8 C 0.9546(3) 0.98560(14) 0.11789(9) 0.0509(4) Uani 1 1 d . . .
C9 C 0.7027(4) 0.93879(13) 0.12408(10) 0.0531(4) Uani 1 1 d . A .
H9A H 0.5982 0.9591 0.0875 0.064 Uiso 1 1 calc R . .
H9B H 0.6267 0.9564 0.1663 0.064 Uiso 1 1 calc R . .
C10 C 0.7548(4) 0.82737(15) 0.12084(10) 0.0569(5) Uani 1 1 d D . .
C11 C 0.6196(5) 0.77492(17) 0.06552(12) 0.0752(6) Uani 1 1 d . A .
H11A H 0.6393 0.8103 0.0242 0.113 Uiso 1 1 calc R . .
H11B H 0.4503 0.7714 0.0767 0.113 Uiso 1 1 calc R . .
H11C H 0.6832 0.7096 0.0605 0.113 Uiso 1 1 calc R . .
C12 C 0.7350(8) 0.7780(3) 0.18766(19) 0.0784(9) Uani 0.85 1 d PDU A 1
H12 H 0.8843 0.7675 0.2082 0.094 Uiso 0.85 1 calc PR A 1
C13 C 0.5592(9) 0.7478(4) 0.2218(2) 0.0919(12) Uani 0.65 1 d PDU A 1
H13A H 0.4018 0.7548 0.2056 0.110 Uiso 0.65 1 calc PR A 1
H13B H 0.5861 0.7183 0.2632 0.110 Uiso 0.65 1 calc PR A 1
C12' C 0.619(3) 0.7902(14) 0.1788(8) 0.066(4) Uani 0.15 1 d PDU A 2
H12' H 0.4535 0.7959 0.1866 0.079 Uiso 0.15 1 calc PR A 2
C13' C 0.796(2) 0.7429(8) 0.2213(5) 0.117(3) Uani 0.35 1 d PDU A 2
H13C H 0.9588 0.7414 0.2086 0.141 Uiso 0.35 1 calc PR A 2
H13D H 0.7483 0.7139 0.2613 0.141 Uiso 0.35 1 calc PR A 2
C14 C 1.0218(5) 1.06535(17) 0.16842(10) 0.0702(6) Uani 1 1 d . . .
H14A H 0.9999 1.0406 0.2131 0.105 Uiso 1 1 calc R . .
H14B H 0.9194 1.1216 0.1618 0.105 Uiso 1 1 calc R . .
H14C H 1.1883 1.0840 0.1622 0.105 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.387(3) . ?
N1 C7 1.403(2) . ?
N1 C3 1.471(3) . ?
O1 C1 1.192(3) . ?
O2 C1 1.341(3) . ?
O2 C2 1.423(3) . ?
O3 C7 1.203(2) . ?
O4 C10 1.453(3) . ?
O4 O5 1.455(2) . ?
O5 C8 1.424(2) . ?
C2 C3 1.519(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.527(3) . ?
C3 H3 0.9800 . ?
C4 C6 1.515(3) . ?
C4 C5 1.516(4) . ?
C4 H4 0.9800 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.540(3) . ?
C8 C14 1.526(3) . ?
C8 C9 1.532(3) . ?
C9 C10 1.544(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C12' 1.466(16) . ?
C10 C12 1.496(4) . ?
C10 C11 1.510(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.253(5) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9300 . ?
C13 H13B 0.9300 . ?
C12' C13' 1.444(14) . ?
C12' H12' 0.9300 . ?
C13' H13C 0.9300 . ?
C13' H13D 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C7 127.69(16) . . ?
C1 N1 C3 111.25(15) . . ?
C7 N1 C3 119.21(15) . . ?
C1 O2 C2 110.57(16) . . ?
C10 O4 O5 103.30(14) . . ?
C8 O5 O4 103.21(13) . . ?
O1 C1 O2 122.30(18) . . ?
O1 C1 N1 128.18(19) . . ?
O2 C1 N1 109.52(18) . . ?
O2 C2 C3 107.52(16) . . ?
O2 C2 H2A 110.2 . . ?
C3 C2 H2A 110.2 . . ?
O2 C2 H2B 110.2 . . ?
C3 C2 H2B 110.2 . . ?
H2A C2 H2B 108.5 . . ?
N1 C3 C2 100.85(16) . . ?
N1 C3 C4 113.31(15) . . ?
C2 C3 C4 114.89(16) . . ?
N1 C3 H3 109.1 . . ?
C2 C3 H3 109.1 . . ?
C4 C3 H3 109.1 . . ?
C6 C4 C5 111.7(2) . . ?
C6 C4 C3 109.63(19) . . ?
C5 C4 C3 113.06(18) . . ?
C6 C4 H4 107.4 . . ?
C5 C4 H4 107.4 . . ?
C3 C4 H4 107.4 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 N1 118.40(17) . . ?
O3 C7 C8 121.21(18) . . ?
N1 C7 C8 120.37(16) . . ?
O5 C8 C14 103.67(16) . . ?
O5 C8 C9 103.65(15) . . ?
C14 C8 C9 117.52(17) . . ?
O5 C8 C7 107.21(15) . . ?
C14 C8 C7 109.92(16) . . ?
C9 C8 C7 113.65(15) . . ?
C8 C9 C10 103.68(15) . . ?
C8 C9 H9A 111.0 . . ?
C10 C9 H9A 111.0 . . ?
C8 C9 H9B 111.0 . . ?
C10 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
O4 C10 C12' 134.6(6) . . ?
O4 C10 C12 108.0(2) . . ?
C12' C10 C12 26.6(6) . . ?
O4 C10 C11 104.02(17) . . ?
C12' C10 C11 99.3(8) . . ?
C12 C10 C11 113.7(2) . . ?
O4 C10 C9 103.18(16) . . ?
C12' C10 C9 102.2(7) . . ?
C12 C10 C9 113.0(2) . . ?
C11 C10 C9 113.75(18) . . ?
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 . . ?
C13 C12 C10 133.4(4) . . ?
C13 C12 H12 113.3 . . ?
C10 C12 H12 113.3 . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
C13' C12' C10 105.8(12) . . ?
C13' C12' H12' 127.1 . . ?
C10 C12' H12' 127.1 . . ?
C12' C13' H13C 120.0 . . ?
C12' C13' H13D 120.0 . . ?
H13C C13' H13D 120.0 . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 O4 O5 C8 -49.51(17) . . . . ?
C2 O2 C1 O1 177.48(19) . . . . ?
C2 O2 C1 N1 -2.3(2) . . . . ?
C7 N1 C1 O1 -10.4(3) . . . . ?
C3 N1 C1 O1 -174.6(2) . . . . ?
C7 N1 C1 O2 169.39(16) . . . . ?
C3 N1 C1 O2 5.19(19) . . . . ?
C1 O2 C2 C3 -1.3(2) . . . . ?
C1 N1 C3 C2 -5.51(18) . . . . ?
C7 N1 C3 C2 -171.22(15) . . . . ?
C1 N1 C3 C4 -128.82(17) . . . . ?
C7 N1 C3 C4 65.5(2) . . . . ?
O2 C2 C3 N1 3.98(19) . . . . ?
O2 C2 C3 C4 126.19(18) . . . . ?
N1 C3 C4 C6 -175.7(2) . . . . ?
C2 C3 C4 C6 69.1(3) . . . . ?
N1 C3 C4 C5 59.0(2) . . . . ?
C2 C3 C4 C5 -56.2(2) . . . . ?
C1 N1 C7 O3 -155.83(17) . . . . ?
C3 N1 C7 O3 7.3(2) . . . . ?
C1 N1 C7 C8 25.8(2) . . . . ?
C3 N1 C7 C8 -171.12(14) . . . . ?
O4 O5 C8 C14 164.05(14) . . . . ?
O4 O5 C8 C9 40.79(16) . . . . ?
O4 O5 C8 C7 -79.70(16) . . . . ?
O3 C7 C8 O5 -16.4(2) . . . . ?
N1 C7 C8 O5 161.92(14) . . . . ?
O3 C7 C8 C14 95.6(2) . . . . ?
N1 C7 C8 C14 -86.0(2) . . . . ?
O3 C7 C8 C9 -130.34(19) . . . . ?
N1 C7 C8 C9 48.0(2) . . . . ?
O5 C8 C9 C10 -17.89(18) . . . . ?
C14 C8 C9 C10 -131.52(18) . . . . ?
C7 C8 C9 C10 98.13(18) . . . . ?
O5 O4 C10 C12' -86.2(11) . . . . ?
O5 O4 C10 C12 -83.7(2) . . . . ?
O5 O4 C10 C11 155.15(14) . . . . ?
O5 O4 C10 C9 36.15(18) . . . . ?
C8 C9 C10 O4 -11.35(19) . . . . ?
C8 C9 C10 C12' 130.6(7) . . . . ?
C8 C9 C10 C12 105.1(2) . . . . ?
C8 C9 C10 C11 -123.37(18) . . . . ?
O4 C10 C12 C13 -166.2(5) . . . . ?
C12' C10 C12 C13 9.8(17) . . . . ?
C11 C10 C12 C13 -51.3(6) . . . . ?
C9 C10 C12 C13 80.3(5) . . . . ?
O4 C10 C12' C13' 1.9(19) . . . . ?
C12 C10 C12' C13' -3.4(9) . . . . ?
C11 C10 C12' C13' 122.3(11) . . . . ?
C9 C10 C12' C13' -120.8(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.028
_database_code_depnum_ccdc_archive 'CCDC 978792'
