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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_compound1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H18 N O4'
_chemical_formula_sum            'C12 H18 N O4'
_chemical_formula_weight         240.27

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   5.4960(9)
_cell_length_b                   12.831(2)
_cell_length_c                   17.881(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.872(3)
_cell_angle_gamma                90.00
_cell_volume                     1258.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0001
_exptl_absorpt_correction_T_max  0.0001
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7893
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_sigmaI/netI    0.0655
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         28.32
_reflns_number_total             3037
_reflns_number_gt                2063
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.1407P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3037
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0791
_refine_ls_wR_factor_ref         0.2435
_refine_ls_wR_factor_gt          0.2230
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1715(3) 0.93495(12) 0.47395(9) 0.0466(4) Uani 1 1 d . . .
O1 O 0.5318(3) 0.80557(15) 0.43543(10) 0.0776(6) Uani 1 1 d . . .
H1 H 0.4256 0.8502 0.4374 0.080 Uiso 1 1 calc . . .
C10 C 0.6293(4) 0.57734(15) 0.41795(10) 0.0461(5) Uani 1 1 d . . .
H10A H 0.6447 0.6020 0.4693 0.055 Uiso 1 1 calc R . .
H10B H 0.4628 0.5538 0.4074 0.055 Uiso 1 1 calc R . .
C11 C 0.6802(3) 0.66739(14) 0.36559(10) 0.0416(4) Uani 1 1 d . . .
H11A H 0.8422 0.6956 0.3801 0.050 Uiso 1 1 calc R . .
C7 C 0.4944(4) 0.75181(15) 0.37403(12) 0.0495(5) Uani 1 1 d . . .
C12 C 0.8585(4) 0.53818(19) 0.27829(13) 0.0603(6) Uani 1 1 d . . .
H12A H 0.8515 0.5140 0.2268 0.072 Uiso 1 1 calc R . .
H12B H 1.0227 0.5629 0.2912 0.072 Uiso 1 1 calc R . .
O2 O 0.5454(3) 0.38137(14) 0.23018(10) 0.0735(6) Uani 1 1 d . . .
H2 H 0.4181 0.3504 0.2184 0.080 Uiso 1 1 calc . . .
C1 C 0.0252(4) 0.90135(14) 0.52607(11) 0.0462(5) Uani 1 1 d . . .
C9 C 0.5708(4) 0.39142(15) 0.30387(13) 0.0532(5) Uani 1 1 d . . .
C8 C 0.6790(4) 0.62827(17) 0.28474(11) 0.0531(6) Uani 1 1 d . . .
H8A H 0.5161 0.6052 0.2682 0.064 Uiso 1 1 calc R . .
H8B H 0.7230 0.6849 0.2524 0.064 Uiso 1 1 calc R . .
O3 O 0.3256(4) 0.76615(18) 0.32981(13) 0.1063(9) Uani 1 1 d . . .
C6 C 0.8016(4) 0.48606(17) 0.40982(12) 0.0547(5) Uani 1 1 d . . .
H6A H 0.7529 0.4290 0.4411 0.066 Uiso 1 1 calc R . .
H6B H 0.9654 0.5068 0.4273 0.066 Uiso 1 1 calc R . .
C2 C 0.1487(4) 1.03220(15) 0.44781(10) 0.0453(5) Uani 1 1 d . . .
C5 C 0.8030(4) 0.44852(16) 0.32892(12) 0.0494(5) Uani 1 1 d . . .
H5A H 0.9372 0.3985 0.3269 0.059 Uiso 1 1 calc R . .
O4 O 0.4286(4) 0.35642(18) 0.34496(12) 0.0903(7) Uani 1 1 d . . .
C4 C 0.3172(5) 1.0645(2) 0.38967(14) 0.0686(7) Uani 1 1 d . . .
H4A H 0.2821 1.1350 0.3746 0.103 Uiso 1 1 calc R . .
H4B H 0.2948 1.0193 0.3470 0.103 Uiso 1 1 calc R . .
H4C H 0.4829 1.0598 0.4101 0.103 Uiso 1 1 calc R . .
C3 C 0.0581(5) 0.79196(16) 0.55365(16) 0.0698(7) Uani 1 1 d . . .
H3A H -0.0575 0.7777 0.5903 0.105 Uiso 1 1 calc R . .
H3B H 0.2205 0.7834 0.5761 0.105 Uiso 1 1 calc R . .
H3C H 0.0323 0.7445 0.5124 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 C2 1.335(3) . ?
N1 C1 1.343(3) . ?
O1 C7 1.301(3) . ?
O1 H1 0.8200 . ?
C10 C6 1.519(3) . ?
C10 C11 1.525(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C7 1.503(3) . ?
C11 C8 1.530(3) . ?
C11 H11A 0.9800 . ?
C7 O3 1.192(3) . ?
C12 C5 1.508(3) . ?
C12 C8 1.529(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O2 C9 1.322(3) . ?
O2 H2 0.8200 . ?
C1 C2 1.385(3) 3_576 ?
C1 C3 1.495(3) . ?
C9 O4 1.196(3) . ?
C9 C5 1.513(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C6 C5 1.525(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C2 C1 1.385(3) 3_576 ?
C2 C4 1.497(3) . ?
C5 H5A 0.9800 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 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
C2 N1 C1 119.76(16) . . ?
C7 O1 H1 109.5 . . ?
C6 C10 C11 112.58(17) . . ?
C6 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C6 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C7 C11 C10 109.29(16) . . ?
C7 C11 C8 111.82(16) . . ?
C10 C11 C8 110.02(15) . . ?
C7 C11 H11A 108.5 . . ?
C10 C11 H11A 108.5 . . ?
C8 C11 H11A 108.5 . . ?
O3 C7 O1 123.3(2) . . ?
O3 C7 C11 123.2(2) . . ?
O1 C7 C11 113.39(17) . . ?
C5 C12 C8 111.95(17) . . ?
C5 C12 H12A 109.2 . . ?
C8 C12 H12A 109.2 . . ?
C5 C12 H12B 109.2 . . ?
C8 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C9 O2 H2 109.5 . . ?
N1 C1 C2 119.72(17) . 3_576 ?
N1 C1 C3 117.76(19) . . ?
C2 C1 C3 122.5(2) 3_576 . ?
O4 C9 O2 123.1(2) . . ?
O4 C9 C5 125.0(2) . . ?
O2 C9 C5 111.9(2) . . ?
C12 C8 C11 110.96(17) . . ?
C12 C8 H8A 109.4 . . ?
C11 C8 H8A 109.4 . . ?
C12 C8 H8B 109.4 . . ?
C11 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C10 C6 C5 112.18(16) . . ?
C10 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C10 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N1 C2 C1 120.52(18) . 3_576 ?
N1 C2 C4 116.99(19) . . ?
C1 C2 C4 122.49(19) 3_576 . ?
C12 C5 C9 113.10(18) . . ?
C12 C5 C6 110.04(16) . . ?
C9 C5 C6 112.05(19) . . ?
C12 C5 H5A 107.1 . . ?
C9 C5 H5A 107.1 . . ?
C6 C5 H5A 107.1 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.074
_database_code_depnum_ccdc_archive 'CCDC 987037'
#######################################################################
#
#                 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_compound2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 N2 O8'
_chemical_formula_sum            'C22 H24 N2 O8'
_chemical_formula_weight         444.43

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   9.6944(4)
_cell_length_b                   17.9372(7)
_cell_length_c                   18.6161(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.427(3)
_cell_angle_gamma                90.00
_cell_volume                     3236.2(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1404
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0001
_exptl_absorpt_correction_T_max  0.0001
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9481
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         24.81
_reflns_number_total             5234
_reflns_number_gt                3661
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.1484P)²+0.9878P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5234
_refine_ls_number_parameters     441
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0781
_refine_ls_wR_factor_ref         0.2540
_refine_ls_wR_factor_gt          0.2250
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
N3 N 0.0692(3) 0.17365(16) 0.12207(14) 0.0566(7) Uani 1 1 d . . .
O10 O -0.2781(3) 0.25470(16) -0.17101(14) 0.0695(8) Uani 1 1 d . . .
O12 O -0.1001(3) 0.23967(16) -0.06716(13) 0.0786(8) Uani 1 1 d . . .
H12 H -0.1407 0.2543 -0.1037 0.080 Uiso 1 1 calc . . .
C32 C -0.2984(3) 0.16523(16) -0.07399(15) 0.0487(7) Uani 1 1 d . . .
O6 O -0.1302(3) 0.15752(17) 0.01881(14) 0.0826(9) Uani 1 1 d . . .
O9 O -0.3406(3) 0.07306(15) 0.01651(13) 0.0774(8) Uani 1 1 d . . .
H9 H -0.2667 0.0902 0.0312 0.080 Uiso 1 1 calc . . .
C31 C -0.3485(3) 0.19951(18) -0.13870(16) 0.0540(8) Uani 1 1 d . . .
C12 C 0.0489(3) 0.22429(19) 0.17439(16) 0.0565(8) Uani 1 1 d . . .
C27 C -0.3799(4) 0.10809(18) -0.04494(17) 0.0558(8) Uani 1 1 d . . .
N1 N 0.2643(3) 0.1887(2) 0.22631(17) 0.0750(9) Uani 1 1 d . . .
C33 C -0.1695(4) 0.18746(19) -0.03864(17) 0.0582(8) Uani 1 1 d . . .
C28 C -0.5008(4) 0.0859(2) -0.0786(2) 0.0663(9) Uani 1 1 d . . .
H28A H -0.5526 0.0474 -0.0594 0.080 Uiso 1 1 calc R . .
C11 C 0.1814(4) 0.1304(2) 0.11936(19) 0.0656(9) Uani 1 1 d . . .
C30 C -0.4689(4) 0.1774(2) -0.1706(2) 0.0710(10) Uani 1 1 d . . .
H30A H -0.5004 0.2004 -0.2127 0.085 Uiso 1 1 calc R . .
C29 C -0.5448(4) 0.1207(2) -0.1406(2) 0.0759(11) Uani 1 1 d . . .
H29A H -0.6272 0.1059 -0.1628 0.091 Uiso 1 1 calc R . .
C10 C 0.1496(4) 0.2303(2) 0.22779(17) 0.0648(9) Uani 1 1 d . . .
C9 C 0.2816(4) 0.1393(3) 0.1739(2) 0.0736(11) Uani 1 1 d . . .
C24 C -0.0799(4) 0.2686(2) 0.1705(2) 0.0795(11) Uani 1 1 d . . .
H24A H -0.1326 0.2548 0.1283 0.119 Uiso 1 1 calc R . .
H24B H -0.0576 0.3207 0.1684 0.119 Uiso 1 1 calc R . .
H24C H -0.1330 0.2590 0.2124 0.119 Uiso 1 1 calc R . .
C3 C 0.1910(5) 0.0753(3) 0.0595(2) 0.0937(14) Uani 1 1 d . . .
H3A H 0.1105 0.0792 0.0286 0.141 Uiso 1 1 calc R . .
H3B H 0.1968 0.0258 0.0790 0.141 Uiso 1 1 calc R . .
H3C H 0.2718 0.0855 0.0324 0.141 Uiso 1 1 calc R . .
C23 C 0.1373(5) 0.2842(3) 0.2886(2) 0.0927(14) Uani 1 1 d . . .
H23A H 0.2164 0.2795 0.3204 0.139 Uiso 1 1 calc R . .
H23B H 0.0552 0.2735 0.3145 0.139 Uiso 1 1 calc R . .
H23C H 0.1325 0.3340 0.2700 0.139 Uiso 1 1 calc R . .
N2 N 0.6108(3) 0.51562(17) 0.04266(14) 0.0609(7) Uani 1 1 d . . .
O11 O 1.0513(3) 0.62226(17) 0.15595(15) 0.0768(8) Uani 1 1 d . . .
C4 C 0.9620(3) 0.52397(19) 0.23016(17) 0.0556(8) Uani 1 1 d . . .
O8 O 0.8288(3) 0.54939(17) 0.12517(14) 0.0793(8) Uani 1 1 d . . .
H8 H 0.7583 0.5375 0.1027 0.080 Uiso 1 1 calc . . .
C2 C 0.9833(4) 0.4815(2) 0.29308(19) 0.0660(9) Uani 1 1 d . . .
C8 C 0.4978(4) 0.5579(2) 0.04790(17) 0.0628(9) Uani 1 1 d . . .
C7 C 0.6168(4) 0.4580(2) -0.00306(17) 0.0615(9) Uani 1 1 d . . .
O5 O 0.7560(3) 0.4608(2) 0.19781(18) 0.1046(11) Uani 1 1 d . . .
C22 C 1.0995(4) 0.4921(2) 0.33706(19) 0.0730(10) Uani 1 1 d . . .
H22A H 1.1130 0.4635 0.3783 0.088 Uiso 1 1 calc R . .
C1 C 0.8405(4) 0.5095(2) 0.1830(2) 0.0694(10) Uani 1 1 d . . .
C18 C 0.2788(4) 0.3292(2) 0.06229(17) 0.0581(8) Uani 1 1 d . . .
C21 C 1.1937(4) 0.5450(2) 0.31897(19) 0.0681(10) Uani 1 1 d . . .
H21A H 1.2714 0.5522 0.3485 0.082 Uiso 1 1 calc R . .
O4 O 0.0682(4) 0.3133(2) 0.00002(19) 0.1041(11) Uani 1 1 d . . .
H4 H 0.0268 0.2875 -0.0298 0.080 Uiso 1 1 calc . . .
C20 C 1.1768(4) 0.5876(2) 0.25891(19) 0.0637(9) Uani 1 1 d . . .
H20A H 1.2426 0.6234 0.2480 0.076 Uiso 1 1 calc R . .
O7 O 0.8923(3) 0.42902(19) 0.31298(17) 0.0958(10) Uani 1 1 d . . .
H7 H 0.8283 0.4272 0.2834 0.080 Uiso 1 1 calc . . .
O3 O 0.2334(5) 0.2341(2) -0.02325(19) 0.1144(12) Uani 1 1 d . . .
C17 C 0.4117(5) 0.3034(3) 0.0771(2) 0.0867(13) Uani 1 1 d . . .
C13 C 0.2325(5) 0.3918(3) 0.0995(2) 0.0815(12) Uani 1 1 d . . .
C19 C 0.1914(5) 0.2891(3) 0.0087(2) 0.0823(12) Uani 1 1 d . . .
O2 O 0.1037(4) 0.4210(2) 0.0865(2) 0.1219(13) Uani 1 1 d . . .
H2 H 0.0634 0.3962 0.0555 0.080 Uiso 1 1 calc . . .
O1 O 0.4651(4) 0.2447(3) 0.0450(2) 0.1325(15) Uani 1 1 d . . .
H1 H 0.4086 0.2277 0.0159 0.080 Uiso 1 1 calc . . .
C15 C 0.4407(5) 0.4012(3) 0.1627(2) 0.0891(14) Uani 1 1 d . . .
H15A H 0.4950 0.4264 0.1966 0.107 Uiso 1 1 calc R . .
C16 C 0.4967(5) 0.3415(4) 0.1302(3) 0.0993(16) Uani 1 1 d . . .
H16A H 0.5860 0.3257 0.1415 0.119 Uiso 1 1 calc R . .
C6 C 0.5014(5) 0.6200(3) 0.1008(2) 0.0913(13) Uani 1 1 d . . .
H6A H 0.4144 0.6455 0.0994 0.137 Uiso 1 1 calc R . .
H6B H 0.5736 0.6542 0.0891 0.137 Uiso 1 1 calc R . .
H6C H 0.5187 0.6003 0.1482 0.137 Uiso 1 1 calc R . .
C5 C 0.7469(5) 0.4138(3) -0.0035(3) 0.0947(14) Uani 1 1 d . . .
H5A H 0.7381 0.3745 -0.0383 0.142 Uiso 1 1 calc R . .
H5B H 0.7641 0.3927 0.0433 0.142 Uiso 1 1 calc R . .
H5C H 0.8223 0.4457 -0.0157 0.142 Uiso 1 1 calc R . .
C14 C 0.3110(6) 0.4270(3) 0.1496(3) 0.0957(14) Uani 1 1 d . . .
H14A H 0.2773 0.4678 0.1745 0.115 Uiso 1 1 calc R . .
C25 C 0.4118(5) 0.0955(4) 0.1743(3) 0.1183(19) Uani 1 1 d . . .
H25A H 0.4677 0.1089 0.2156 0.177 Uiso 1 1 calc R . .
H25B H 0.4613 0.1060 0.1314 0.177 Uiso 1 1 calc R . .
H25C H 0.3906 0.0432 0.1761 0.177 Uiso 1 1 calc R . .
C26 C 1.0620(3) 0.57802(18) 0.21377(17) 0.0546(8) Uani 1 1 d . . .
H10 H -0.224(4) 0.268(2) -0.148(2) 0.068(14) Uiso 1 1 d . . .
H11 H 0.982(5) 0.607(3) 0.135(3) 0.104(18) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 C11 1.338(5) . ?
N3 C12 1.350(4) . ?
O10 C31 1.352(4) . ?
O10 H10 0.71(4) . ?
O12 C33 1.276(4) . ?
O12 H12 0.8200 . ?
C32 C27 1.410(5) . ?
C32 C31 1.427(4) . ?
C32 C33 1.454(4) . ?
O6 C33 1.248(4) . ?
O9 C27 1.352(4) . ?
O9 H9 0.8200 . ?
C31 C30 1.355(5) . ?
C12 C10 1.380(5) . ?
C12 C24 1.480(5) . ?
C27 C28 1.374(5) . ?
N1 C9 1.331(5) . ?
N1 C10 1.341(5) . ?
C28 C29 1.370(5) . ?
C28 H28A 0.9300 . ?
C11 C9 1.396(5) . ?
C11 C3 1.493(6) . ?
C30 C29 1.382(6) . ?
C30 H30A 0.9300 . ?
C29 H29A 0.9300 . ?
C10 C23 1.495(5) . ?
C9 C25 1.488(6) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
N2 C8 1.338(4) . ?
N2 C7 1.341(4) . ?
O11 C26 1.339(4) . ?
O11 H11 0.81(5) . ?
C4 C2 1.409(5) . ?
C4 C26 1.410(5) . ?
C4 C1 1.474(5) . ?
O8 C1 1.296(5) . ?
O8 H8 0.8200 . ?
C2 O7 1.348(5) . ?
C2 C22 1.389(5) . ?
C8 C7 1.402(5) 3_665 ?
C8 C6 1.487(5) . ?
C7 C8 1.402(5) 3_665 ?
C7 C5 1.490(5) . ?
O5 C1 1.233(5) . ?
C22 C21 1.366(6) . ?
C22 H22A 0.9300 . ?
C18 C17 1.391(6) . ?
C18 C13 1.400(6) . ?
C18 C19 1.479(6) . ?
C21 C20 1.361(5) . ?
C21 H21A 0.9300 . ?
O4 C19 1.277(6) . ?
O4 H4 0.8200 . ?
C20 C26 1.389(5) . ?
C20 H20A 0.9300 . ?
O7 H7 0.8200 . ?
O3 C19 1.227(6) . ?
C17 O1 1.321(6) . ?
C17 C16 1.443(7) . ?
C13 C14 1.345(6) . ?
C13 O2 1.370(6) . ?
O2 H2 0.8200 . ?
O1 H1 0.8200 . ?
C15 C16 1.350(7) . ?
C15 C14 1.356(7) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C14 H14A 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C11 N3 C12 123.4(3) . . ?
C31 O10 H10 111(3) . . ?
C33 O12 H12 109.5 . . ?
C27 C32 C31 117.1(3) . . ?
C27 C32 C33 120.6(3) . . ?
C31 C32 C33 122.3(3) . . ?
C27 O9 H9 109.5 . . ?
O10 C31 C30 117.2(3) . . ?
O10 C31 C32 121.8(3) . . ?
C30 C31 C32 121.0(3) . . ?
N3 C12 C10 117.4(3) . . ?
N3 C12 C24 117.6(3) . . ?
C10 C12 C24 125.0(3) . . ?
O9 C27 C28 118.1(3) . . ?
O9 C27 C32 120.9(3) . . ?
C28 C27 C32 121.0(3) . . ?
C9 N1 C10 120.3(3) . . ?
O6 C33 O12 121.3(3) . . ?
O6 C33 C32 120.7(3) . . ?
O12 C33 C32 118.0(3) . . ?
C29 C28 C27 119.7(3) . . ?
C29 C28 H28A 120.1 . . ?
C27 C28 H28A 120.1 . . ?
N3 C11 C9 117.2(3) . . ?
N3 C11 C3 118.5(4) . . ?
C9 C11 C3 124.3(4) . . ?
C31 C30 C29 119.9(3) . . ?
C31 C30 H30A 120.0 . . ?
C29 C30 H30A 120.0 . . ?
C28 C29 C30 121.2(3) . . ?
C28 C29 H29A 119.4 . . ?
C30 C29 H29A 119.4 . . ?
N1 C10 C12 120.9(3) . . ?
N1 C10 C23 117.2(3) . . ?
C12 C10 C23 121.9(4) . . ?
N1 C9 C11 120.8(4) . . ?
N1 C9 C25 118.0(4) . . ?
C11 C9 C25 121.2(4) . . ?
C12 C24 H24A 109.5 . . ?
C12 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C12 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C11 C3 H3A 109.5 . . ?
C11 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C11 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C10 C23 H23A 109.5 . . ?
C10 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C10 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C8 N2 C7 122.1(3) . . ?
C26 O11 H11 103(4) . . ?
C2 C4 C26 117.7(3) . . ?
C2 C4 C1 119.9(3) . . ?
C26 C4 C1 122.4(3) . . ?
C1 O8 H8 109.5 . . ?
O7 C2 C22 117.4(3) . . ?
O7 C2 C4 121.5(3) . . ?
C22 C2 C4 121.1(3) . . ?
N2 C8 C7 118.6(3) . 3_665 ?
N2 C8 C6 117.8(3) . . ?
C7 C8 C6 123.5(4) 3_665 . ?
N2 C7 C8 119.2(3) . 3_665 ?
N2 C7 C5 117.6(3) . . ?
C8 C7 C5 123.1(4) 3_665 . ?
C21 C22 C2 119.2(3) . . ?
C21 C22 H22A 120.4 . . ?
C2 C22 H22A 120.4 . . ?
O5 C1 O8 122.1(3) . . ?
O5 C1 C4 121.2(4) . . ?
O8 C1 C4 116.7(3) . . ?
C17 C18 C13 118.4(4) . . ?
C17 C18 C19 119.0(4) . . ?
C13 C18 C19 122.6(4) . . ?
C20 C21 C22 121.7(3) . . ?
C20 C21 H21A 119.1 . . ?
C22 C21 H21A 119.1 . . ?
C19 O4 H4 109.5 . . ?
C21 C20 C26 120.4(3) . . ?
C21 C20 H20A 119.8 . . ?
C26 C20 H20A 119.8 . . ?
C2 O7 H7 109.5 . . ?
O1 C17 C18 123.1(5) . . ?
O1 C17 C16 117.6(5) . . ?
C18 C17 C16 119.2(5) . . ?
C14 C13 O2 116.2(5) . . ?
C14 C13 C18 122.4(5) . . ?
O2 C13 C18 121.4(4) . . ?
O3 C19 O4 122.2(4) . . ?
O3 C19 C18 121.8(4) . . ?
O4 C19 C18 116.0(4) . . ?
C13 O2 H2 109.5 . . ?
C17 O1 H1 109.5 . . ?
C16 C15 C14 124.8(4) . . ?
C16 C15 H15A 117.6 . . ?
C14 C15 H15A 117.6 . . ?
C15 C16 C17 117.0(4) . . ?
C15 C16 H16A 121.5 . . ?
C17 C16 H16A 121.5 . . ?
C8 C6 H6A 109.5 . . ?
C8 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C8 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C7 C5 H5A 109.5 . . ?
C7 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C7 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C13 C14 C15 118.1(5) . . ?
C13 C14 H14A 120.9 . . ?
C15 C14 H14A 120.9 . . ?
C9 C25 H25A 109.5 . . ?
C9 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C9 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O11 C26 C20 117.2(3) . . ?
O11 C26 C4 122.8(3) . . ?
C20 C26 C4 120.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.938
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 987038'
#######################################################################
#
#                 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_compound3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H13 N2 O5'
_chemical_formula_sum            'C11 H13 N2 O5'
_chemical_formula_weight         253.23

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   7.3345(7)
_cell_length_b                   10.9381(11)
_cell_length_c                   15.0352(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.804(2)
_cell_angle_gamma                90.00
_cell_volume                     1204.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0001
_exptl_absorpt_correction_T_max  0.0001
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7473
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_av_sigmaI/netI    0.0660
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         28.27
_reflns_number_total             2903
_reflns_number_gt                2257
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0899P)²+0.1825P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2903
_refine_ls_number_parameters     179
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1768
_refine_ls_wR_factor_gt          0.1634
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.002

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 0.15675(17) 0.62120(12) 0.42586(8) 0.0406(3) Uani 1 1 d . . .
O4 O 0.3406(2) 0.35264(13) 0.52283(9) 0.0609(4) Uani 1 1 d . . .
O2 O -0.0078(2) 0.76430(12) 0.29879(8) 0.0642(4) Uani 1 1 d . . .
N2 N 0.44667(18) 0.12042(13) 0.49659(9) 0.0473(3) Uani 1 1 d . . .
O3 O -0.0156(2) 0.91906(12) 0.39377(9) 0.0632(4) Uani 1 1 d D . .
O1 O 0.2997(2) 0.40341(14) 0.37967(9) 0.0710(4) Uani 1 1 d . . .
C7 C 0.0964(2) 0.73053(14) 0.44899(9) 0.0414(3) Uani 1 1 d . . .
C8 C 0.2310(3) 0.58004(19) 0.57930(11) 0.0574(5) Uani 1 1 d . . .
H8 H 0.2759 0.5258 0.6227 0.080 Uiso 1 1 calc . . .
C11 C 0.0193(2) 0.80584(15) 0.37273(10) 0.0448(4) Uani 1 1 d . . .
C4 C 0.5009(2) 0.06918(16) 0.57464(10) 0.0451(4) Uani 1 1 d . . .
C10 C 0.2898(2) 0.42738(16) 0.45792(11) 0.0475(4) Uani 1 1 d . . .
C9 C 0.2240(2) 0.54770(15) 0.48999(10) 0.0425(4) Uani 1 1 d . . .
C6 C 0.1019(3) 0.77249(17) 0.53629(11) 0.0569(5) Uani 1 1 d . . .
H6 H 0.0613 0.8505 0.5500 0.080 Uiso 1 1 calc . . .
C3 C 0.4451(2) 0.05275(16) 0.42183(10) 0.0475(4) Uani 1 1 d . . .
C2 C 0.5006(3) 0.14774(18) 0.65644(11) 0.0562(4) Uani 1 1 d . . .
H2A H 0.4585 0.2283 0.6404 0.080 Uiso 1 1 calc . . .
H2B H 0.6221 0.1526 0.6829 0.080 Uiso 1 1 calc . . .
H2C H 0.4209 0.1126 0.6983 0.080 Uiso 1 1 calc . . .
C5 C 0.1700(3) 0.6939(2) 0.60223(11) 0.0692(6) Uani 1 1 d . . .
H5 H 0.1744 0.7182 0.6616 0.080 Uiso 1 1 calc . . .
C1 C 0.3849(3) 0.1137(2) 0.33605(13) 0.0684(6) Uani 1 1 d . . .
H1A H 0.3535 0.1973 0.3474 0.080 Uiso 1 1 calc . . .
H1B H 0.2804 0.0718 0.3100 0.080 Uiso 1 1 calc . . .
H1C H 0.4824 0.1112 0.2957 0.080 Uiso 1 1 calc . . .
O1W O 0.1416(3) 0.54290(14) 0.23783(9) 0.0713(5) Uani 1 1 d D . .
H1WB H 0.089(3) 0.6036(18) 0.2588(16) 0.082(8) Uiso 1 1 d D . .
H3 H -0.056(3) 0.961(2) 0.3481(14) 0.081(7) Uiso 1 1 d D . .
H1WA H 0.181(4) 0.499(2) 0.2783(16) 0.103(10) Uiso 1 1 d D . .
H4 H 0.378(3) 0.275(3) 0.5022(17) 0.085(8) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.327(2) . ?
N1 C9 1.331(2) . ?
O4 C10 1.313(2) . ?
O4 H4 0.95(3) . ?
O2 C11 1.2083(19) . ?
N2 C4 1.3431(19) . ?
N2 C3 1.345(2) . ?
O3 C11 1.307(2) . ?
O3 H3 0.866(16) . ?
O1 C10 1.211(2) . ?
C7 C6 1.389(2) . ?
C7 C11 1.500(2) . ?
C8 C5 1.373(3) . ?
C8 C9 1.387(2) . ?
C8 H8 0.9300 . ?
C4 C3 1.391(2) 3_656 ?
C4 C2 1.500(2) . ?
C10 C9 1.490(2) . ?
C6 C5 1.387(3) . ?
C6 H6 0.9300 . ?
C3 C4 1.391(2) 3_656 ?
C3 C1 1.499(2) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C5 H5 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
O1W H1WB 0.838(16) . ?
O1W H1WA 0.814(16) . ?

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
C7 N1 C9 118.08(13) . . ?
C10 O4 H4 112.9(16) . . ?
C4 N2 C3 119.37(14) . . ?
C11 O3 H3 112.0(18) . . ?
N1 C7 C6 123.41(15) . . ?
N1 C7 C11 114.38(13) . . ?
C6 C7 C11 122.21(15) . . ?
C5 C8 C9 118.51(16) . . ?
C5 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
O2 C11 O3 123.64(15) . . ?
O2 C11 C7 122.38(15) . . ?
O3 C11 C7 113.98(13) . . ?
N2 C4 C3 120.32(15) . 3_656 ?
N2 C4 C2 117.70(15) . . ?
C3 C4 C2 121.97(14) 3_656 . ?
O1 C10 O4 123.98(17) . . ?
O1 C10 C9 122.78(15) . . ?
O4 C10 C9 113.21(14) . . ?
N1 C9 C8 122.81(15) . . ?
N1 C9 C10 114.42(13) . . ?
C8 C9 C10 122.77(15) . . ?
C5 C6 C7 117.61(17) . . ?
C5 C6 H6 121.2 . . ?
C7 C6 H6 121.2 . . ?
N2 C3 C4 120.31(14) . 3_656 ?
N2 C3 C1 117.64(16) . . ?
C4 C3 C1 122.05(16) 3_656 . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C8 C5 C6 119.54(16) . . ?
C8 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
H1WB O1W H1WA 110(2) . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        28.27
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.084
_database_code_depnum_ccdc_archive 'CCDC 987039'
#######################################################################
#
#                 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_compound4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H28 N2 O6'
_chemical_formula_sum            'C30 H28 N2 O6'
_chemical_formula_weight         512.54

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   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                   14.650(7)
_cell_length_b                   12.512(6)
_cell_length_c                   14.649(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.13
_cell_angle_gamma                90.00
_cell_volume                     2681(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0001
_exptl_absorpt_correction_T_max  0.0001
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16329
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_av_sigmaI/netI    0.0571
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.39
_diffrn_reflns_theta_max         28.59
_reflns_number_total             6388
_reflns_number_gt                3827
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.1096P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6388
_refine_ls_number_parameters     347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.2065
_refine_ls_wR_factor_gt          0.1806
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C24 C 0.10143(12) 0.51832(14) 0.20134(12) 0.0467(4) Uani 1 1 d . . .
C21 C -0.07506(12) 0.53302(14) 0.10883(12) 0.0482(4) Uani 1 1 d . . .
C26 C -0.05824(12) 0.45464(14) 0.17358(12) 0.0489(4) Uani 1 1 d . . .
H26A H -0.1045 0.4069 0.1863 0.059 Uiso 1 1 calc R . .
C25 C 0.02925(12) 0.44514(14) 0.22185(12) 0.0455(4) Uani 1 1 d . . .
C23 C 0.08252(13) 0.59715(16) 0.13176(13) 0.0562(5) Uani 1 1 d . . .
H23A H 0.1285 0.6438 0.1161 0.067 Uiso 1 1 calc R . .
C22 C -0.00244(13) 0.60474(16) 0.08790(13) 0.0558(5) Uani 1 1 d . . .
H22A H -0.0132 0.6573 0.0438 0.067 Uiso 1 1 calc R . .
O1 O -0.18576(10) 0.62178(12) 0.00973(11) 0.0747(5) Uani 1 1 d . . .
C27 C 0.04707(13) 0.36753(15) 0.29164(13) 0.0532(5) Uani 1 1 d . . .
H27A H 0.0016 0.3191 0.3053 0.064 Uiso 1 1 calc R . .
C30 C 0.18723(12) 0.51193(17) 0.25203(13) 0.0564(5) Uani 1 1 d . . .
H30A H 0.2341 0.5586 0.2388 0.068 Uiso 1 1 calc R . .
C29 C 0.20121(12) 0.43744(17) 0.32019(13) 0.0568(5) Uani 1 1 d . . .
O6 O 0.28424(9) 0.43932(15) 0.37011(11) 0.0828(5) Uani 1 1 d . . .
H6 H 0.2852 0.3918 0.4087 0.080 Uiso 1 1 calc . . .
C28 C 0.13094(13) 0.36323(16) 0.33934(14) 0.0568(5) Uani 1 1 d . . .
H28A H 0.1417 0.3115 0.3843 0.068 Uiso 1 1 calc R . .
O5 O -0.22925(10) 0.47818(14) 0.08791(12) 0.0858(5) Uani 1 1 d . . .
H5 H -0.2786 0.4909 0.0609 0.080 Uiso 1 1 calc . . .
C20 C -0.16816(13) 0.54898(16) 0.06378(14) 0.0556(5) Uani 1 1 d . . .
C16 C 0.35540(13) 0.85975(15) 0.23119(13) 0.0519(5) Uani 1 1 d . . .
C12 C 0.45098(12) 0.75998(14) 0.34349(12) 0.0475(4) Uani 1 1 d . . .
C17 C 0.36423(13) 0.78206(15) 0.29689(13) 0.0519(5) Uani 1 1 d . . .
H17A H 0.3131 0.7429 0.3116 0.062 Uiso 1 1 calc R . .
C19 C 0.61607(13) 0.80222(16) 0.36897(13) 0.0556(5) Uani 1 1 d . . .
H19A H 0.6672 0.8418 0.3550 0.067 Uiso 1 1 calc R . .
C13 C 0.52931(12) 0.82276(14) 0.32121(12) 0.0482(4) Uani 1 1 d . . .
C18 C 0.26327(14) 0.87624(16) 0.18101(14) 0.0552(5) Uani 1 1 d . . .
O4 O 0.70490(11) 0.70562(14) 0.48561(11) 0.0732(5) Uani 1 1 d . . .
C9 C 0.62349(13) 0.72475(16) 0.43475(13) 0.0562(5) Uani 1 1 d . . .
O3 O 0.26201(11) 0.96012(14) 0.12520(12) 0.0877(6) Uani 1 1 d . . .
H3 H 0.2114 0.9652 0.0988 0.080 Uiso 1 1 calc . . .
O2 O 0.19713(10) 0.81847(12) 0.19058(11) 0.0721(4) Uani 1 1 d . . .
C14 C 0.51827(13) 0.90231(16) 0.25302(13) 0.0571(5) Uani 1 1 d . . .
H14A H 0.5683 0.9430 0.2377 0.068 Uiso 1 1 calc R . .
C15 C 0.43451(13) 0.92029(17) 0.20905(14) 0.0568(5) Uani 1 1 d . . .
H15A H 0.4289 0.9727 0.1641 0.068 Uiso 1 1 calc R . .
C11 C 0.46222(14) 0.67764(16) 0.41020(14) 0.0577(5) Uani 1 1 d . . .
H11A H 0.4126 0.6353 0.4239 0.069 Uiso 1 1 calc R . .
N2 N 0.08984(11) 0.99027(14) 0.03622(10) 0.0581(4) Uani 1 1 d . . .
C10 C 0.54648(15) 0.66037(16) 0.45460(14) 0.0610(5) Uani 1 1 d . . .
H10A H 0.5532 0.6062 0.4979 0.073 Uiso 1 1 calc R . .
C6 C 0.03598(14) 1.07246(16) 0.06148(13) 0.0569(5) Uani 1 1 d . . .
C5 C 0.05518(14) 0.91787(16) -0.02500(13) 0.0577(5) Uani 1 1 d . . .
C8 C 0.11947(17) 0.82928(19) -0.05189(18) 0.0773(7) Uani 1 1 d . . .
H8A H 0.0885 0.7835 -0.0962 0.116 Uiso 1 1 calc R . .
H8B H 0.1382 0.7883 0.0013 0.116 Uiso 1 1 calc R . .
H8C H 0.1722 0.8601 -0.0778 0.116 Uiso 1 1 calc R . .
C7 C 0.07838(18) 1.15049(18) 0.13027(16) 0.0771(7) Uani 1 1 d . . .
H7A H 0.0348 1.2052 0.1426 0.116 Uiso 1 1 calc R . .
H7B H 0.1315 1.1824 0.1060 0.116 Uiso 1 1 calc R . .
H7C H 0.0957 1.1134 0.1859 0.116 Uiso 1 1 calc R . .
N1 N 0.59279(10) 0.50015(12) 0.02668(10) 0.0493(4) Uani 1 1 d . . .
C4 C 0.53401(13) 0.56720(14) 0.06644(11) 0.0473(4) Uani 1 1 d . . .
C3 C 0.55978(13) 0.43269(14) -0.03911(12) 0.0498(4) Uani 1 1 d . . .
C2 C 0.57509(17) 0.64051(17) 0.14029(15) 0.0710(6) Uani 1 1 d . . .
H2A H 0.5278 0.6842 0.1637 0.106 Uiso 1 1 calc R . .
H2B H 0.6204 0.6854 0.1149 0.106 Uiso 1 1 calc R . .
H2C H 0.6030 0.5983 0.1889 0.106 Uiso 1 1 calc R . .
C1 C 0.62920(18) 0.3604(2) -0.08169(18) 0.0837(8) Uani 1 1 d . . .
H1A H 0.5988 0.3164 -0.1276 0.126 Uiso 1 1 calc R . .
H1B H 0.6580 0.3157 -0.0352 0.126 Uiso 1 1 calc R . .
H1C H 0.6746 0.4033 -0.1091 0.126 Uiso 1 1 calc R . .
H4 H 0.7362(19) 0.762(2) 0.4896(19) 0.107(10) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C24 C30 1.427(3) . ?
C24 C23 1.434(3) . ?
C24 C25 1.443(2) . ?
C21 C26 1.377(3) . ?
C21 C22 1.438(3) . ?
C21 C20 1.496(3) . ?
C26 C25 1.435(2) . ?
C26 H26A 0.9300 . ?
C25 C27 1.424(3) . ?
C23 C22 1.372(3) . ?
C23 H23A 0.9300 . ?
C22 H22A 0.9300 . ?
O1 C20 1.225(2) . ?
C27 C28 1.381(3) . ?
C27 H27A 0.9300 . ?
C30 C29 1.373(3) . ?
C30 H30A 0.9300 . ?
C29 O6 1.385(2) . ?
C29 C28 1.425(3) . ?
O6 H6 0.8200 . ?
C28 H28A 0.9300 . ?
O5 C20 1.321(2) . ?
O5 H5 0.8200 . ?
C16 C17 1.369(3) . ?
C16 C15 1.436(3) . ?
C16 C18 1.515(3) . ?
C12 C11 1.423(3) . ?
C12 C17 1.436(3) . ?
C12 C13 1.443(3) . ?
C17 H17A 0.9300 . ?
C19 C9 1.367(3) . ?
C19 C13 1.440(3) . ?
C19 H19A 0.9300 . ?
C13 C14 1.413(3) . ?
C18 O2 1.223(2) . ?
C18 O3 1.330(3) . ?
O4 C9 1.392(2) . ?
O4 H4 0.85(3) . ?
C9 C10 1.429(3) . ?
O3 H3 0.8200 . ?
C14 C15 1.373(3) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C11 C10 1.380(3) . ?
C11 H11A 0.9300 . ?
N2 C5 1.354(3) . ?
N2 C6 1.360(3) . ?
C10 H10A 0.9300 . ?
C6 C5 1.416(3) 3_575 ?
C6 C7 1.512(3) . ?
C5 C6 1.416(3) 3_575 ?
C5 C8 1.520(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
N1 C3 1.351(2) . ?
N1 C4 1.356(2) . ?
C4 C3 1.410(3) 3_665 ?
C4 C2 1.518(3) . ?
C3 C4 1.410(3) 3_665 ?
C3 C1 1.520(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
C30 C24 C23 122.61(17) . . ?
C30 C24 C25 119.40(17) . . ?
C23 C24 C25 117.97(16) . . ?
C26 C21 C22 118.99(16) . . ?
C26 C21 C20 121.57(16) . . ?
C22 C21 C20 119.35(17) . . ?
C21 C26 C25 121.33(16) . . ?
C21 C26 H26A 119.3 . . ?
C25 C26 H26A 119.3 . . ?
C27 C25 C26 122.30(16) . . ?
C27 C25 C24 118.33(16) . . ?
C26 C25 C24 119.34(16) . . ?
C22 C23 C24 121.01(17) . . ?
C22 C23 H23A 119.5 . . ?
C24 C23 H23A 119.5 . . ?
C23 C22 C21 121.32(18) . . ?
C23 C22 H22A 119.3 . . ?
C21 C22 H22A 119.3 . . ?
C28 C27 C25 120.87(17) . . ?
C28 C27 H27A 119.6 . . ?
C25 C27 H27A 119.6 . . ?
C29 C30 C24 120.58(17) . . ?
C29 C30 H30A 119.7 . . ?
C24 C30 H30A 119.7 . . ?
C30 C29 O6 117.67(18) . . ?
C30 C29 C28 120.30(17) . . ?
O6 C29 C28 122.01(18) . . ?
C29 O6 H6 109.5 . . ?
C27 C28 C29 120.47(18) . . ?
C27 C28 H28A 119.8 . . ?
C29 C28 H28A 119.8 . . ?
C20 O5 H5 109.5 . . ?
O1 C20 O5 123.35(18) . . ?
O1 C20 C21 122.62(18) . . ?
O5 C20 C21 114.02(17) . . ?
C17 C16 C15 119.12(18) . . ?
C17 C16 C18 119.03(18) . . ?
C15 C16 C18 121.80(18) . . ?
C11 C12 C17 122.13(17) . . ?
C11 C12 C13 119.06(17) . . ?
C17 C12 C13 118.81(17) . . ?
C16 C17 C12 121.19(18) . . ?
C16 C17 H17A 119.4 . . ?
C12 C17 H17A 119.4 . . ?
C9 C19 C13 120.20(18) . . ?
C9 C19 H19A 119.9 . . ?
C13 C19 H19A 119.9 . . ?
C14 C13 C19 122.21(18) . . ?
C14 C13 C12 118.79(17) . . ?
C19 C13 C12 119.00(17) . . ?
O2 C18 O3 123.54(19) . . ?
O2 C18 C16 123.65(19) . . ?
O3 C18 C16 112.81(18) . . ?
C9 O4 H4 109.8(19) . . ?
C19 C9 O4 122.15(19) . . ?
C19 C9 C10 120.66(18) . . ?
O4 C9 C10 117.19(19) . . ?
C18 O3 H3 109.5 . . ?
C15 C14 C13 120.79(18) . . ?
C15 C14 H14A 119.6 . . ?
C13 C14 H14A 119.6 . . ?
C14 C15 C16 121.28(19) . . ?
C14 C15 H15A 119.4 . . ?
C16 C15 H15A 119.4 . . ?
C10 C11 C12 120.26(18) . . ?
C10 C11 H11A 119.9 . . ?
C12 C11 H11A 119.9 . . ?
C5 N2 C6 118.95(17) . . ?
C11 C10 C9 120.75(19) . . ?
C11 C10 H10A 119.6 . . ?
C9 C10 H10A 119.6 . . ?
N2 C6 C5 120.73(18) . 3_575 ?
N2 C6 C7 116.51(19) . . ?
C5 C6 C7 122.8(2) 3_575 . ?
N2 C5 C6 120.31(19) . 3_575 ?
N2 C5 C8 116.38(19) . . ?
C6 C5 C8 123.3(2) 3_575 . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 N1 C4 118.82(15) . . ?
N1 C4 C3 120.69(16) . 3_665 ?
N1 C4 C2 116.34(18) . . ?
C3 C4 C2 122.97(18) 3_665 . ?
N1 C3 C4 120.49(16) . 3_665 ?
N1 C3 C1 116.32(19) . . ?
C4 C3 C1 123.18(18) 3_665 . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.934
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 987040'
#######################################################################
#
#                 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_compound5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 N2 O7'
_chemical_formula_weight         297.24

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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8574(13)
_cell_length_b                   8.3711(11)
_cell_length_c                   11.1437(13)
_cell_angle_alpha                88.282(2)
_cell_angle_beta                 72.1630(10)
_cell_angle_gamma                84.647(2)
_cell_volume                     694.70(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             310
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0001
_exptl_absorpt_correction_T_max  0.0001
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4452
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         28.30
_reflns_number_total             3172
_reflns_number_gt                2641
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.1007P)²+0.2194P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3172
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1872
_refine_ls_wR_factor_gt          0.1773
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.002
_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 0.31881(19) 0.49474(16) 0.04658(14) 0.0383(3) Uani 1 1 d . . .
O4 O -0.02993(16) 0.47263(16) 0.13932(12) 0.0450(3) Uani 1 1 d . . .
H4 H 0.0774 0.4860 0.1162 0.080 Uiso 1 1 calc . . .
O2 O -0.08052(19) 0.26019(18) 0.36687(16) 0.0597(4) Uani 1 1 d . . .
C12 C -0.3039(2) 0.5144(2) 0.29496(15) 0.0356(4) Uani 1 1 d . . .
O1 O -0.03205(18) 0.60958(18) 0.30834(15) 0.0551(4) Uani 1 1 d . . .
C7 C -0.3639(2) 0.3701(2) 0.35146(16) 0.0378(4) Uani 1 1 d . . .
C6 C -0.1053(2) 0.5380(2) 0.24871(17) 0.0378(4) Uani 1 1 d . . .
C4 C 0.3862(2) 0.63143(19) -0.00308(17) 0.0382(4) Uani 1 1 d . . .
C11 C -0.4349(2) 0.6320(2) 0.28115(17) 0.0404(4) Uani 1 1 d . . .
C3 C 0.4283(2) 0.36323(19) 0.05086(16) 0.0380(4) Uani 1 1 d . . .
N2 N -0.3825(2) 0.7861(2) 0.22164(18) 0.0545(4) Uani 1 1 d . . .
C10 C -0.6163(2) 0.6096(3) 0.31970(18) 0.0473(4) Uani 1 1 d . . .
H10A H -0.6997 0.6911 0.3094 0.057 Uiso 1 1 calc R . .
C9 C -0.6715(3) 0.4661(3) 0.37325(19) 0.0502(5) Uani 1 1 d . . .
H9A H -0.7927 0.4490 0.3986 0.060 Uiso 1 1 calc R . .
C8 C -0.5459(3) 0.3471(2) 0.38925(18) 0.0460(4) Uani 1 1 d . . .
H8A H -0.5836 0.2501 0.4259 0.055 Uiso 1 1 calc R . .
O1W O -0.1019(3) 0.8724(2) 0.4620(2) 0.0784(6) Uani 1 1 d . . .
O3 O -0.3087(2) 0.10907(19) 0.4185(2) 0.0825(7) Uani 1 1 d . . .
H3 H -0.2334 0.0413 0.4308 0.080 Uiso 1 1 calc . . .
C5 C -0.2337(2) 0.2412(2) 0.37765(17) 0.0420(4) Uani 1 1 d . . .
C2 C 0.3416(3) 0.2154(2) 0.1082(2) 0.0535(5) Uani 1 1 d . . .
H2A H 0.4327 0.1300 0.1068 0.080 Uiso 1 1 calc R . .
H2B H 0.2666 0.1843 0.0608 0.080 Uiso 1 1 calc R . .
H2C H 0.2700 0.2372 0.1938 0.080 Uiso 1 1 calc R . .
O6 O -0.5004(3) 0.8901(2) 0.2237(3) 0.1068(9) Uani 1 1 d . . .
C1 C 0.2548(3) 0.7736(2) -0.0029(2) 0.0548(5) Uani 1 1 d . . .
H1A H 0.3187 0.8636 -0.0410 0.082 Uiso 1 1 calc R . .
H1B H 0.1848 0.7996 0.0823 0.082 Uiso 1 1 calc R . .
H1C H 0.1768 0.7485 -0.0499 0.082 Uiso 1 1 calc R . .
O5 O -0.2272(3) 0.8018(2) 0.1674(2) 0.0888(7) Uani 1 1 d . . .
H1WB H -0.057(5) 0.854(5) 0.520(4) 0.106(12) Uiso 1 1 d . . .
H1WA H -0.082(5) 0.795(5) 0.419(4) 0.099(12) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.338(2) . ?
N1 C3 1.342(2) . ?
O4 C6 1.294(2) . ?
O4 H4 0.8200 . ?
O2 C5 1.198(2) . ?
C12 C11 1.396(2) . ?
C12 C7 1.399(2) . ?
C12 C6 1.516(2) . ?
O1 C6 1.206(2) . ?
C7 C8 1.391(3) . ?
C7 C5 1.501(2) . ?
C4 C3 1.395(3) 2_665 ?
C4 C1 1.501(2) . ?
C11 C10 1.386(3) . ?
C11 N2 1.468(3) . ?
C3 C4 1.395(3) 2_665 ?
C3 C2 1.499(2) . ?
N2 O5 1.202(3) . ?
N2 O6 1.206(2) . ?
C10 C9 1.373(3) . ?
C10 H10A 0.9300 . ?
C9 C8 1.383(3) . ?
C9 H9A 0.9300 . ?
C8 H8A 0.9300 . ?
O1W H1WB 0.83(4) . ?
O1W H1WA 0.79(4) . ?
O3 C5 1.305(2) . ?
O3 H3 0.8200 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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 C3 120.50(15) . . ?
C6 O4 H4 109.5 . . ?
C11 C12 C7 116.77(15) . . ?
C11 C12 C6 122.40(16) . . ?
C7 C12 C6 120.81(14) . . ?
C8 C7 C12 120.45(16) . . ?
C8 C7 C5 119.15(16) . . ?
C12 C7 C5 120.34(15) . . ?
O1 C6 O4 126.18(16) . . ?
O1 C6 C12 122.91(16) . . ?
O4 C6 C12 110.91(14) . . ?
N1 C4 C3 119.62(15) . 2_665 ?
N1 C4 C1 117.21(16) . . ?
C3 C4 C1 123.17(16) 2_665 . ?
C10 C11 C12 122.82(17) . . ?
C10 C11 N2 117.09(16) . . ?
C12 C11 N2 120.07(16) . . ?
N1 C3 C4 119.88(15) . 2_665 ?
N1 C3 C2 116.97(16) . . ?
C4 C3 C2 123.14(16) 2_665 . ?
O5 N2 O6 122.5(2) . . ?
O5 N2 C11 119.67(16) . . ?
O6 N2 C11 117.75(19) . . ?
C9 C10 C11 119.27(17) . . ?
C9 C10 H10A 120.4 . . ?
C11 C10 H10A 120.4 . . ?
C10 C9 C8 119.58(17) . . ?
C10 C9 H9A 120.2 . . ?
C8 C9 H9A 120.2 . . ?
C9 C8 C7 121.09(18) . . ?
C9 C8 H8A 119.5 . . ?
C7 C8 H8A 119.5 . . ?
H1WB O1W H1WA 108(4) . . ?
C5 O3 H3 109.5 . . ?
O2 C5 O3 124.10(17) . . ?
O2 C5 C7 123.56(16) . . ?
O3 C5 C7 112.28(16) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.917
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.075
_database_code_depnum_ccdc_archive 'CCDC 987041'
#######################################################################
#
#                 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_compound6

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N2 O4'
_chemical_formula_sum            'C16 H18 N2 O4'
_chemical_formula_weight         302.32

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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5343(14)
_cell_length_b                   8.9454(17)
_cell_length_c                   12.885(3)
_cell_angle_alpha                99.769(4)
_cell_angle_beta                 103.689(4)
_cell_angle_gamma                108.465(3)
_cell_volume                     771.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0001
_exptl_absorpt_correction_T_max  0.0001
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4994
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_sigmaI/netI    0.0793
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         28.36
_reflns_number_total             3537
_reflns_number_gt                2786
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.1743P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3537
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0873
_refine_ls_wR_factor_ref         0.2474
_refine_ls_wR_factor_gt          0.2292
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.0987(2) 0.65567(17) 0.59750(14) 0.0561(4) Uani 1 1 d . . .
H3 H 0.1806 0.6450 0.5679 0.080 Uiso 1 1 calc . . .
N2 N 0.3622(2) 0.55607(19) 0.52558(13) 0.0430(4) Uani 1 1 d . . .
O1 O 0.2729(2) 0.7765(2) 0.83397(14) 0.0579(4) Uani 1 1 d . . .
C12 C -0.0254(2) 0.8366(2) 0.67791(15) 0.0378(4) Uani 1 1 d . . .
C16 C 0.1199(3) 0.8096(2) 0.62238(15) 0.0418(4) Uani 1 1 d . . .
O4 O 0.2351(2) 0.9173(2) 0.59997(16) 0.0653(5) Uani 1 1 d . . .
C13 C -0.1518(3) 0.9058(2) 0.62750(17) 0.0473(5) Uani 1 1 d . . .
H13 H -0.1381 0.9408 0.5649 0.080 Uiso 1 1 calc . . .
C15 C 0.1058(3) 0.7328(2) 0.83517(15) 0.0420(4) Uani 1 1 d . . .
O2 O 0.0366(2) 0.6328(2) 0.89270(14) 0.0627(5) Uani 1 1 d . . .
H2 H 0.1239 0.6056 0.9251 0.080 Uiso 1 1 calc . . .
C11 C -0.0430(2) 0.7889(2) 0.77351(16) 0.0396(4) Uani 1 1 d . . .
C8 C 0.4240(3) 0.5879(2) 0.44108(15) 0.0427(4) Uani 1 1 d . . .
C14 C -0.2985(3) 0.9224(2) 0.6708(2) 0.0542(6) Uani 1 1 d . . .
H14 H -0.3847 0.9668 0.6361 0.080 Uiso 1 1 calc . . .
C7 C 0.4347(3) 0.4681(2) 0.58551(15) 0.0430(4) Uani 1 1 d . . .
C10 C -0.1900(3) 0.8084(3) 0.81604(19) 0.0513(5) Uani 1 1 d . . .
H10 H -0.2024 0.7768 0.8799 0.080 Uiso 1 1 calc . . .
C9 C -0.3178(3) 0.8742(3) 0.7642(2) 0.0561(6) Uani 1 1 d . . .
H9 H -0.4167 0.8858 0.7927 0.080 Uiso 1 1 calc . . .
C6 C 0.3365(4) 0.6847(4) 0.3762(2) 0.0696(7) Uani 1 1 d . . .
H6A H 0.2437 0.7120 0.4076 0.080 Uiso 1 1 calc . . .
H6B H 0.2706 0.6211 0.3007 0.080 Uiso 1 1 calc . . .
H6C H 0.4390 0.7832 0.3786 0.080 Uiso 1 1 calc . . .
C5 C 0.3570(5) 0.4319(4) 0.6776(2) 0.0726(7) Uani 1 1 d . . .
H5A H 0.2615 0.4808 0.6818 0.080 Uiso 1 1 calc . . .
H5B H 0.4631 0.4756 0.7461 0.080 Uiso 1 1 calc . . .
H5C H 0.2959 0.3157 0.6646 0.080 Uiso 1 1 calc . . .
N1 N 0.3364(2) 0.53950(18) 0.98531(12) 0.0451(4) Uani 1 1 d . . .
C3 C 0.3206(3) 0.3886(2) 0.93924(14) 0.0439(4) Uani 1 1 d . . .
C2 C 0.5134(3) 0.6512(2) 1.04614(15) 0.0458(5) Uani 1 1 d . . .
C4 C 0.1178(3) 0.2690(3) 0.8732(2) 0.0635(6) Uani 1 1 d . . .
H4A H 0.0249 0.3214 0.8744 0.080 Uiso 1 1 calc . . .
H4B H 0.0848 0.1780 0.9048 0.080 Uiso 1 1 calc . . .
H4C H 0.1138 0.2307 0.7981 0.080 Uiso 1 1 calc . . .
C1 C 0.5201(4) 0.8175(3) 1.0968(2) 0.0742(8) Uani 1 1 d . . .
H1A H 0.3895 0.8186 1.0768 0.080 Uiso 1 1 calc . . .
H1B H 0.6028 0.8974 1.0700 0.080 Uiso 1 1 calc . . .
H1C H 0.5721 0.8430 1.1759 0.080 Uiso 1 1 calc . . .


_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
O3 C16 1.308(2) . ?
O3 H3 0.8200 . ?
N2 C8 1.321(2) . ?
N2 C7 1.339(2) . ?
O1 C15 1.199(2) . ?
C12 C13 1.389(2) . ?
C12 C11 1.392(3) . ?
C12 C16 1.499(2) . ?
C16 O4 1.203(2) . ?
C13 C14 1.387(3) . ?
C13 H13 0.9300 . ?
C15 O2 1.317(2) . ?
C15 C11 1.487(2) . ?
O2 H2 0.8200 . ?
C11 C10 1.391(3) . ?
C8 C7 1.398(3) 2_666 ?
C8 C6 1.494(3) . ?
C14 C9 1.369(4) . ?
C14 H14 0.9300 . ?
C7 C8 1.398(3) 2_666 ?
C7 C5 1.481(3) . ?
C10 C9 1.381(3) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
N1 C3 1.335(2) . ?
N1 C2 1.337(2) . ?
C3 C2 1.385(3) 2_667 ?
C3 C4 1.498(3) . ?
C2 C3 1.385(3) 2_667 ?
C2 C1 1.500(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
C16 O3 H3 109.5 . . ?
C8 N2 C7 119.50(15) . . ?
C13 C12 C11 119.74(17) . . ?
C13 C12 C16 117.41(17) . . ?
C11 C12 C16 122.78(14) . . ?
O4 C16 O3 125.13(18) . . ?
O4 C16 C12 123.04(17) . . ?
O3 C16 C12 111.76(16) . . ?
C14 C13 C12 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
O1 C15 O2 123.51(16) . . ?
O1 C15 C11 123.25(18) . . ?
O2 C15 C11 113.23(16) . . ?
C15 O2 H2 109.5 . . ?
C10 C11 C12 119.37(17) . . ?
C10 C11 C15 120.39(18) . . ?
C12 C11 C15 119.99(15) . . ?
N2 C8 C7 120.62(16) . 2_666 ?
N2 C8 C6 117.28(17) . . ?
C7 C8 C6 122.10(19) 2_666 . ?
C9 C14 C13 120.66(18) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
N2 C7 C8 119.88(17) . 2_666 ?
N2 C7 C5 117.53(17) . . ?
C8 C7 C5 122.58(18) 2_666 . ?
C9 C10 C11 120.6(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C14 C9 C10 119.79(18) . . ?
C14 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C8 C6 H6A 109.5 . . ?
C8 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C8 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C7 C5 H5A 109.5 . . ?
C7 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C7 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 N1 C2 119.36(16) . . ?
N1 C3 C2 120.19(17) . 2_667 ?
N1 C3 C4 116.63(18) . . ?
C2 C3 C4 123.18(18) 2_667 . ?
N1 C2 C3 120.45(17) . 2_667 ?
N1 C2 C1 116.56(18) . . ?
C3 C2 C1 122.99(19) 2_667 . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.921
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.104
_database_code_depnum_ccdc_archive 'CCDC 987042'
#######################################################################
#
#                 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_compound7

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 N O4'
_chemical_formula_sum            'C12 H12 N O4'
_chemical_formula_weight         234.23

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   7.4101(6)
_cell_length_b                   10.2133(9)
_cell_length_c                   15.0232(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.937(9)
_cell_angle_gamma                90.00
_cell_volume                     1130.88(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             492
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0001
_exptl_absorpt_correction_T_max  0.0001
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3956
_diffrn_reflns_av_R_equivalents  0.0126
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.41
_diffrn_reflns_theta_max         27.35
_reflns_number_total             2123
_reflns_number_gt                1727
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0927P)²+0.4994P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2123
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1611
_refine_ls_wR_factor_gt          0.1532
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O -0.0111(2) 0.63351(17) 0.93238(10) 0.0490(5) Uani 1 1 d . . .
H4 H -0.1110 0.5998 0.9346 0.080 Uiso 1 1 calc . . .
C7 C 0.2097(3) 0.6958(2) 0.83883(12) 0.0326(5) Uani 1 1 d . . .
O2 O 0.2179(2) 0.94319(18) 1.00535(12) 0.0578(5) Uani 1 1 d . . .
O3 O -0.0105(2) 0.91448(18) 0.89898(12) 0.0579(5) Uani 1 1 d . . .
H3 H -0.0632 0.9598 0.9332 0.080 Uiso 1 1 calc . . .
O1 O -0.0663(2) 0.59049(19) 0.78637(11) 0.0572(5) Uani 1 1 d . . .
C12 C 0.2697(3) 0.8126(2) 0.88046(13) 0.0344(5) Uani 1 1 d . . .
C5 C 0.0280(3) 0.63532(19) 0.84882(14) 0.0351(5) Uani 1 1 d . . .
C11 C 0.4431(3) 0.8590(2) 0.86991(16) 0.0444(6) Uani 1 1 d . . .
H11A H 0.4837 0.9363 0.8980 0.053 Uiso 1 1 calc R . .
C6 C 0.1508(3) 0.8938(2) 0.93282(15) 0.0382(5) Uani 1 1 d . . .
C8 C 0.3240(3) 0.6295(2) 0.78641(14) 0.0396(5) Uani 1 1 d . . .
H8A H 0.2845 0.5525 0.7576 0.047 Uiso 1 1 calc R . .
C9 C 0.4967(3) 0.6769(3) 0.77658(14) 0.0465(6) Uani 1 1 d . . .
H9A H 0.5725 0.6312 0.7419 0.056 Uiso 1 1 calc R . .
C10 C 0.5550(3) 0.7910(3) 0.81796(16) 0.0484(6) Uani 1 1 d . . .
H10A H 0.6704 0.8229 0.8111 0.058 Uiso 1 1 calc R . .
N1 N 0.1647(2) 0.96304(16) 0.47312(10) 0.0336(4) Uani 1 1 d . . .
C4 C 0.0871(3) 0.8928(2) 0.53430(13) 0.0341(5) Uani 1 1 d . . .
C3 C 0.0805(3) 1.07042(19) 0.43865(13) 0.0340(5) Uani 1 1 d . . .
C2 C 0.1886(4) 0.7749(3) 0.57221(18) 0.0596(7) Uani 1 1 d . . .
H2A H 0.1200 0.7328 0.6149 0.089 Uiso 1 1 calc R . .
H2B H 0.3043 0.8016 0.6012 0.089 Uiso 1 1 calc R . .
H2C H 0.2066 0.7148 0.5248 0.089 Uiso 1 1 calc R . .
C1 C 0.1724(4) 1.1452(2) 0.37041(18) 0.0550(7) Uani 1 1 d . . .
H1A H 0.0995 1.2195 0.3507 0.083 Uiso 1 1 calc R . .
H1B H 0.1876 1.0895 0.3203 0.083 Uiso 1 1 calc R . .
H1C H 0.2890 1.1747 0.3966 0.083 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
O4 C5 1.317(3) . ?
O4 H4 0.8200 . ?
C7 C8 1.391(3) . ?
C7 C12 1.398(3) . ?
C7 C5 1.503(3) . ?
O2 C6 1.256(3) . ?
O3 C6 1.267(3) . ?
O3 H3 0.8200 . ?
O1 C5 1.201(3) . ?
C12 C11 1.394(3) . ?
C12 C6 1.492(3) . ?
C11 C10 1.383(3) . ?
C11 H11A 0.9300 . ?
C8 C9 1.390(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.369(4) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
N1 C3 1.339(3) . ?
N1 C4 1.341(3) . ?
C4 C3 1.398(3) 3_576 ?
C4 C2 1.501(3) . ?
C3 C4 1.398(3) 3_576 ?
C3 C1 1.498(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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 O4 H4 109.5 . . ?
C8 C7 C12 119.03(19) . . ?
C8 C7 C5 117.43(18) . . ?
C12 C7 C5 123.54(18) . . ?
C6 O3 H3 109.5 . . ?
C11 C12 C7 119.6(2) . . ?
C11 C12 C6 118.14(19) . . ?
C7 C12 C6 122.21(18) . . ?
O1 C5 O4 124.84(19) . . ?
O1 C5 C7 122.25(19) . . ?
O4 C5 C7 112.87(17) . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
O2 C6 O3 123.6(2) . . ?
O2 C6 C12 118.57(18) . . ?
O3 C6 C12 117.69(19) . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8A 119.6 . . ?
C7 C8 H8A 119.6 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C9 C10 C11 120.2(2) . . ?
C9 C10 H10A 119.9 . . ?
C11 C10 H10A 119.9 . . ?
C3 N1 C4 119.15(17) . . ?
N1 C4 C3 120.83(18) . 3_576 ?
N1 C4 C2 117.11(19) . . ?
C3 C4 C2 122.06(19) 3_576 . ?
N1 C3 C4 120.02(18) . 3_576 ?
N1 C3 C1 117.10(19) . . ?
C4 C3 C1 122.87(19) 3_576 . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.829
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 987043'
#######################################################################
#
#                 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_compound8

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H24 N3 O3'
_chemical_formula_sum            'C19 H24 N3 O3'
_chemical_formula_weight         342.41

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   9.3995(12)
_cell_length_b                   17.904(2)
_cell_length_c                   11.3775(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.243(2)
_cell_angle_gamma                90.00
_cell_volume                     1911.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             732
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0001
_exptl_absorpt_correction_T_max  0.0001
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12163
_diffrn_reflns_av_R_equivalents  0.0994
_diffrn_reflns_av_sigmaI/netI    0.0719
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         28.55
_reflns_number_total             4648
_reflns_number_gt                2630
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.1300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4648
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0712
_refine_ls_wR_factor_ref         0.2241
_refine_ls_wR_factor_gt          0.1963
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.002
_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
N2 N 0.48055(16) 0.06578(9) 0.66884(13) 0.0574(4) Uani 1 1 d . . .
N3 N 1.39669(16) -0.44744(8) 0.50839(13) 0.0579(4) Uani 1 1 d . . .
C14 C 1.01820(19) -0.26211(10) 0.46557(15) 0.0520(4) Uani 1 1 d . . .
O2 O 1.20686(19) -0.33805(9) 0.53681(14) 0.0879(6) Uani 1 1 d . . .
N1 N 0.68787(18) -0.04119(10) 0.70253(15) 0.0668(5) Uani 1 1 d . . .
C18 C 0.8271(2) -0.14788(11) 0.49511(18) 0.0641(5) Uani 1 1 d . . .
H18 H 0.7621 -0.1097 0.5058 0.080 Uiso 1 1 calc . . .
C16 C 0.9122(2) -0.24792(11) 0.38027(17) 0.0618(5) Uani 1 1 d . . .
H16 H 0.9056 -0.2769 0.3123 0.080 Uiso 1 1 calc . . .
O3 O 0.7130(2) -0.18048(11) 0.30788(16) 0.1091(7) Uani 1 1 d . . .
H3 H 0.6629 -0.1450 0.3246 0.080 Uiso 1 1 calc . . .
C12 C 0.44519(19) -0.00652(11) 0.67682(16) 0.0555(5) Uani 1 1 d . . .
C2 C 1.36023(19) -0.51911(11) 0.49411(16) 0.0576(5) Uani 1 1 d . . .
C3 C 1.5330(2) -0.42692(10) 0.51388(16) 0.0569(5) Uani 1 1 d . . .
C11 C 0.5515(2) -0.06045(10) 0.69351(17) 0.0586(5) Uani 1 1 d . . .
O1 O 1.1186(2) -0.36007(11) 0.35698(15) 0.1157(8) Uani 1 1 d . . .
C10 C 0.6183(2) 0.08526(10) 0.67586(17) 0.0576(5) Uani 1 1 d . . .
C15 C 1.0309(2) -0.21819(11) 0.56620(16) 0.0629(5) Uani 1 1 d . . .
H15 H 1.1033 -0.2272 0.6236 0.080 Uiso 1 1 calc . . .
C9 C 0.7231(2) 0.03099(12) 0.69320(17) 0.0611(5) Uani 1 1 d . . .
C13 C 1.1185(2) -0.32436(12) 0.44640(18) 0.0643(5) Uani 1 1 d . . .
C19 C 0.8154(2) -0.19099(11) 0.39468(18) 0.0611(5) Uani 1 1 d . . .
C17 C 0.9351(3) -0.16123(11) 0.58000(18) 0.0708(6) Uani 1 1 d . . .
H17 H 0.9430 -0.1314 0.6470 0.080 Uiso 1 1 calc . . .
C1 C 1.2053(2) -0.53906(15) 0.4883(2) 0.0854(7) Uani 1 1 d . . .
H1A H 1.1495 -0.4947 0.4969 0.080 Uiso 1 1 calc . . .
H1B H 1.1871 -0.5733 0.5506 0.080 Uiso 1 1 calc . . .
H1C H 1.1799 -0.5620 0.4137 0.080 Uiso 1 1 calc . . .
C8 C 0.6544(3) 0.16659(12) 0.6640(2) 0.0850(7) Uani 1 1 d . . .
H8A H 0.5682 0.1951 0.6528 0.080 Uiso 1 1 calc . . .
H8B H 0.7116 0.1734 0.5976 0.080 Uiso 1 1 calc . . .
H8C H 0.7065 0.1832 0.7342 0.080 Uiso 1 1 calc . . .
C4 C 1.5684(3) -0.34574(12) 0.5294(2) 0.0805(7) Uani 1 1 d . . .
H4A H 1.4819 -0.3175 0.5330 0.080 Uiso 1 1 calc . . .
H4B H 1.6200 -0.3288 0.4640 0.080 Uiso 1 1 calc . . .
H4C H 1.6258 -0.3389 0.6011 0.080 Uiso 1 1 calc . . .
C7 C 0.8790(2) 0.05012(16) 0.7027(3) 0.0936(8) Uani 1 1 d . . .
H7A H 0.9339 0.0053 0.7147 0.080 Uiso 1 1 calc . . .
H7B H 0.8979 0.0833 0.7681 0.080 Uiso 1 1 calc . . .
H7C H 0.9049 0.0741 0.6315 0.080 Uiso 1 1 calc . . .
C6 C 0.2907(2) -0.02584(15) 0.6677(2) 0.0819(7) Uani 1 1 d . . .
H6A H 0.2353 0.0190 0.6584 0.080 Uiso 1 1 calc . . .
H6B H 0.2659 -0.0512 0.7380 0.080 Uiso 1 1 calc . . .
H6C H 0.2713 -0.0578 0.6010 0.080 Uiso 1 1 calc . . .
C5 C 0.5156(3) -0.14189(12) 0.6994(2) 0.0912(8) Uani 1 1 d . . .
H5A H 0.6019 -0.1704 0.7101 0.080 Uiso 1 1 calc . . .
H5B H 0.4651 -0.1568 0.6275 0.080 Uiso 1 1 calc . . .
H5C H 0.4570 -0.1506 0.7644 0.080 Uiso 1 1 calc . . .
H2 H 1.274(3) -0.3757(15) 0.520(2) 0.101(8) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C10 1.339(2) . ?
N2 C12 1.341(2) . ?
N3 C3 1.331(2) . ?
N3 C2 1.336(2) . ?
C14 C16 1.375(2) . ?
C14 C15 1.389(3) . ?
C14 C13 1.484(2) . ?
O2 C13 1.308(2) . ?
O2 H2 0.95(3) . ?
N1 C11 1.326(2) . ?
N1 C9 1.340(3) . ?
C18 C19 1.378(3) . ?
C18 C17 1.382(3) . ?
C18 H18 0.9300 . ?
C16 C19 1.382(3) . ?
C16 H16 0.9300 . ?
O3 C19 1.353(2) . ?
O3 H3 0.8200 . ?
C12 C11 1.395(3) . ?
C12 C6 1.491(3) . ?
C2 C3 1.400(3) 3_846 ?
C2 C1 1.497(3) . ?
C3 C2 1.400(3) 3_846 ?
C3 C4 1.499(3) . ?
C11 C5 1.499(3) . ?
O1 C13 1.202(2) . ?
C10 C9 1.390(3) . ?
C10 C8 1.503(3) . ?
C15 C17 1.375(3) . ?
C15 H15 0.9300 . ?
C9 C7 1.503(3) . ?
C17 H17 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 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
C10 N2 C12 119.35(15) . . ?
C3 N3 C2 120.70(15) . . ?
C16 C14 C15 120.16(16) . . ?
C16 C14 C13 118.43(16) . . ?
C15 C14 C13 121.40(16) . . ?
C13 O2 H2 112.1(16) . . ?
C11 N1 C9 119.14(16) . . ?
C19 C18 C17 120.23(16) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C14 C16 C19 120.54(17) . . ?
C14 C16 H16 119.7 . . ?
C19 C16 H16 119.7 . . ?
C19 O3 H3 109.5 . . ?
N2 C12 C11 119.94(17) . . ?
N2 C12 C6 117.62(17) . . ?
C11 C12 C6 122.44(19) . . ?
N3 C2 C3 119.41(18) . 3_846 ?
N3 C2 C1 118.47(17) . . ?
C3 C2 C1 122.11(19) 3_846 . ?
N3 C3 C2 119.88(18) . 3_846 ?
N3 C3 C4 118.66(17) . . ?
C2 C3 C4 121.46(19) 3_846 . ?
N1 C11 C12 120.84(18) . . ?
N1 C11 C5 117.93(19) . . ?
C12 C11 C5 121.2(2) . . ?
N2 C10 C9 120.11(18) . . ?
N2 C10 C8 118.02(17) . . ?
C9 C10 C8 121.87(19) . . ?
C17 C15 C14 119.20(17) . . ?
C17 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
N1 C9 C10 120.60(18) . . ?
N1 C9 C7 117.30(18) . . ?
C10 C9 C7 122.1(2) . . ?
O1 C13 O2 122.38(17) . . ?
O1 C13 C14 123.69(17) . . ?
O2 C13 C14 113.92(16) . . ?
O3 C19 C18 123.19(16) . . ?
O3 C19 C16 117.52(17) . . ?
C18 C19 C16 119.29(17) . . ?
C15 C17 C18 120.55(17) . . ?
C15 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C10 C8 H8A 109.5 . . ?
C10 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C10 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C9 C7 H7A 109.5 . . ?
C9 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C9 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C12 C6 H6A 109.5 . . ?
C12 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C12 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C11 C5 H5A 109.5 . . ?
C11 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C11 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.131
_database_code_depnum_ccdc_archive 'CCDC 987044'
