# 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_ADI3PIC

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H24 N2 O4'
_chemical_formula_weight         332.39

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                   5.4732(11)
_cell_length_b                   14.309(3)
_cell_length_c                   11.659(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.48(3)
_cell_angle_gamma                90.00
_cell_volume                     900.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1517
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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            4023
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         27.47
_reflns_number_total             2051
_reflns_number_gt                1517
_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)+(0.0653P)²+0.1143P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2051
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1292
_refine_ls_wR_factor_gt          0.1160
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
O8 O 0.07428(18) 0.79621(7) 0.53515(10) 0.0515(3) Uani 1 1 d . . .
O10 O 0.37813(18) 0.69643(7) 0.59984(10) 0.0555(3) Uani 1 1 d . . .
N1 N 0.3968(2) 0.92688(8) 0.62481(10) 0.0426(3) Uani 1 1 d . . .
C3 C 0.5332(3) 1.08475(9) 0.66829(11) 0.0421(3) Uani 1 1 d . . .
C9 C 0.1697(2) 0.71123(9) 0.55100(11) 0.0400(3) Uani 1 1 d . . .
C12 C 0.0917(2) 0.53735(9) 0.52595(12) 0.0410(3) Uani 1 1 d . . .
H12A H 0.1323 0.5279 0.6111 0.049 Uiso 1 1 calc R . .
H13B H 0.2466 0.5304 0.4933 0.049 Uiso 1 1 calc R . .
C11 C -0.0088(2) 0.63557(9) 0.50170(12) 0.0422(3) Uani 1 1 d . . .
H11B H -0.0515 0.6443 0.4165 0.051 Uiso 1 1 calc R . .
H11A H -0.1631 0.6423 0.5349 0.051 Uiso 1 1 calc R . .
C6 C 0.6172(2) 0.89584(11) 0.67826(12) 0.0475(4) Uani 1 1 d . . .
H6 H 0.6475 0.8304 0.6814 0.057 Uiso 1 1 calc R . .
C2 C 0.3589(2) 1.01928(10) 0.62018(11) 0.0415(3) Uani 1 1 d . . .
H2 H 0.2031 1.0414 0.5816 0.050 Uiso 1 1 calc R . .
C4 C 0.7593(3) 1.05054(11) 0.72437(12) 0.0492(4) Uani 1 1 d . . .
H4 H 0.8842 1.0924 0.7594 0.059 Uiso 1 1 calc R . .
C5 C 0.8014(3) 0.95544(11) 0.72887(13) 0.0530(4) Uani 1 1 d . . .
H5 H 0.9557 0.9314 0.7665 0.064 Uiso 1 1 calc R . .
C7 C 0.4760(3) 1.18751(10) 0.65938(15) 0.0564(4) Uani 1 1 d . . .
H7A H 0.6158 1.2228 0.7017 0.085 Uiso 1 1 calc R . .
H7B H 0.3269 1.2003 0.6932 0.085 Uiso 1 1 calc R . .
H7C H 0.4480 1.2063 0.5774 0.085 Uiso 1 1 calc R . .
H8 H 0.1947 0.8411 0.5671 0.076(6) Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O8 0.0419(5) 0.0342(5) 0.0730(7) -0.0043(4) -0.0067(5) 0.0024(4)
O10 0.0433(6) 0.0419(6) 0.0743(8) 0.0069(5) -0.0105(5) -0.0007(4)
N1 0.0400(6) 0.0398(6) 0.0463(6) -0.0008(5) 0.0019(5) -0.0037(5)
C3 0.0464(7) 0.0432(8) 0.0368(7) -0.0033(5) 0.0078(5) -0.0076(6)
C9 0.0387(7) 0.0364(7) 0.0439(7) 0.0024(5) 0.0036(6) 0.0015(5)
C12 0.0398(7) 0.0366(7) 0.0453(7) -0.0021(5) 0.0029(5) 0.0021(6)
C11 0.0398(7) 0.0348(7) 0.0497(8) -0.0016(6) 0.0009(6) 0.0009(5)
C6 0.0430(8) 0.0430(8) 0.0544(8) -0.0002(6) 0.0019(6) 0.0011(6)
C2 0.0401(7) 0.0434(8) 0.0397(7) -0.0001(6) 0.0025(5) -0.0021(6)
C4 0.0417(8) 0.0552(9) 0.0494(8) -0.0085(7) 0.0032(6) -0.0128(6)
C5 0.0375(7) 0.0585(10) 0.0596(9) -0.0031(7) -0.0016(6) 0.0003(7)
C7 0.0684(10) 0.0428(9) 0.0562(9) -0.0059(7) 0.0047(8) -0.0088(7)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O8 C9 1.3242(16) . ?
O8 H8 0.9509 . ?
O10 C9 1.2069(16) . ?
N1 C2 1.3382(17) . ?
N1 C6 1.3387(17) . ?
C3 C2 1.3880(19) . ?
C3 C4 1.390(2) . ?
C3 C7 1.503(2) . ?
C9 C11 1.5072(18) . ?
C12 C11 1.5185(18) . ?
C12 C12 1.522(3) 3_566 ?
C12 H12A 0.9900 . ?
C12 H13B 0.9900 . ?
C11 H11B 0.9900 . ?
C11 H11A 0.9900 . ?
C6 C5 1.377(2) . ?
C6 H6 0.9500 . ?
C2 H2 0.9500 . ?
C4 C5 1.380(2) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O8 H8 109.5 . . ?
C2 N1 C6 117.94(12) . . ?
C2 C3 C4 116.88(13) . . ?
C2 C3 C7 120.70(13) . . ?
C4 C3 C7 122.42(13) . . ?
O10 C9 O8 123.18(12) . . ?
O10 C9 C11 123.83(12) . . ?
O8 C9 C11 112.99(11) . . ?
C11 C12 C12 112.41(13) . 3_566 ?
C11 C12 H12A 109.1 . . ?
C12 C12 H12A 109.1 3_566 . ?
C11 C12 H13B 109.1 . . ?
C12 C12 H13B 109.1 3_566 . ?
H12A C12 H13B 107.9 . . ?
C9 C11 C12 113.70(11) . . ?
C9 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C9 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
H11B C11 H11A 107.7 . . ?
N1 C6 C5 122.27(14) . . ?
N1 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
N1 C2 C3 123.96(12) . . ?
N1 C2 H2 118.0 . . ?
C3 C2 H2 118.0 . . ?
C5 C4 C3 119.69(13) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C6 C5 C4 119.25(13) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 O10 0.95 2.51 3.2086(19) 130.6 .
C4 H4 O10 0.95 2.43 3.3403(18) 161.0 2_656
O8 H8 N1 0.95 1.71 2.6641(15) 176.4 .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 1008278'
#######################################################################
#
#                 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_FUM4PIC

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_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           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                   8.7460(17)
_cell_length_b                   7.2170(14)
_cell_length_c                   12.799(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.68(3)
_cell_angle_gamma                90.00
_cell_volume                     807.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1547
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      28.37

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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            6600
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         28.37
_reflns_number_total             2015
_reflns_number_gt                1547
_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)+(0.0528P)²+0.1393P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2015
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1140
_refine_ls_wR_factor_gt          0.1048
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
O8 O 0.55979(10) 0.69589(12) 0.41987(7) 0.0357(3) Uani 1 1 d . . .
O10 O 0.73607(11) 0.71825(14) 0.55076(8) 0.0435(3) Uani 1 1 d . . .
N1 N 0.68594(12) 0.38348(14) 0.37610(8) 0.0298(3) Uani 1 1 d . . .
C11 C 0.56091(13) 0.96431(16) 0.52473(9) 0.0278(3) Uani 1 1 d . . .
H11 H 0.6093 1.0344 0.5797 0.033 Uiso 1 1 calc R . .
C4 C 0.84088(14) 0.05893(17) 0.32592(10) 0.0300(3) Uani 1 1 d . . .
C2 C 0.63977(14) 0.27894(17) 0.29448(10) 0.0303(3) Uani 1 1 d . . .
H2 H 0.5522 0.3171 0.2533 0.036 Uiso 1 1 calc R . .
C9 C 0.62724(13) 0.78021(17) 0.49961(9) 0.0280(3) Uani 1 1 d . . .
C6 C 0.80981(15) 0.32777(18) 0.43281(10) 0.0320(3) Uani 1 1 d . . .
H6 H 0.8443 0.4005 0.4911 0.038 Uiso 1 1 calc R . .
C5 C 0.88936(14) 0.16934(18) 0.41011(10) 0.0322(3) Uani 1 1 d . . .
H5 H 0.9775 0.1354 0.4520 0.039 Uiso 1 1 calc R . .
C3 C 0.71346(14) 0.11792(18) 0.26710(10) 0.0301(3) Uani 1 1 d . . .
H3 H 0.6768 0.0482 0.2082 0.036 Uiso 1 1 calc R . .
C7 C 0.92439(18) -0.1159(2) 0.29928(13) 0.0472(4) Uani 1 1 d . . .
H7A H 0.9055 -0.2111 0.3517 0.071 Uiso 1 1 calc R . .
H7B H 1.0344 -0.0907 0.2986 0.071 Uiso 1 1 calc R . .
H7C H 0.8876 -0.1598 0.2301 0.071 Uiso 1 1 calc R . .
H8 H 0.6131 0.5893 0.4094 0.086(7) Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O8 0.0425(5) 0.0283(5) 0.0352(5) -0.0083(4) -0.0104(4) 0.0105(4)
O10 0.0449(6) 0.0376(5) 0.0462(6) -0.0089(5) -0.0173(4) 0.0138(4)
N1 0.0363(6) 0.0238(5) 0.0291(5) -0.0016(4) 0.0002(4) 0.0035(4)
C11 0.0326(6) 0.0248(6) 0.0259(6) -0.0019(5) 0.0005(5) 0.0002(5)
C4 0.0337(6) 0.0267(6) 0.0302(6) 0.0013(5) 0.0085(5) 0.0021(5)
C2 0.0320(6) 0.0296(6) 0.0289(6) 0.0017(5) -0.0017(5) 0.0016(5)
C9 0.0311(6) 0.0253(6) 0.0274(6) -0.0003(5) 0.0001(5) 0.0014(5)
C6 0.0381(7) 0.0282(6) 0.0291(6) -0.0025(5) -0.0028(5) -0.0005(5)
C5 0.0321(6) 0.0324(7) 0.0318(6) 0.0027(5) -0.0013(5) 0.0034(5)
C3 0.0353(6) 0.0287(6) 0.0263(6) -0.0032(5) 0.0029(5) -0.0020(5)
C7 0.0527(9) 0.0408(8) 0.0485(9) -0.0087(7) 0.0047(7) 0.0171(7)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O8 C9 1.3052(14) . ?
O8 H8 0.9128 . ?
O10 C9 1.2150(14) . ?
N1 C2 1.3357(16) . ?
N1 C6 1.3374(17) . ?
C11 C11 1.318(2) 3_676 ?
C11 C9 1.4908(17) . ?
C11 H11 0.9500 . ?
C4 C3 1.3826(18) . ?
C4 C5 1.3904(18) . ?
C4 C7 1.5051(18) . ?
C2 C3 1.3819(18) . ?
C2 H2 0.9500 . ?
C6 C5 1.3765(18) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C3 H3 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O8 H8 107.0 . . ?
C2 N1 C6 117.53(11) . . ?
C11 C11 C9 123.95(14) 3_676 . ?
C11 C11 H11 118.0 3_676 . ?
C9 C11 H11 118.0 . . ?
C3 C4 C5 117.02(12) . . ?
C3 C4 C7 121.48(12) . . ?
C5 C4 C7 121.50(12) . . ?
N1 C2 C3 123.08(11) . . ?
N1 C2 H2 118.5 . . ?
C3 C2 H2 118.5 . . ?
O10 C9 O8 124.31(12) . . ?
O10 C9 C11 120.98(11) . . ?
O8 C9 C11 114.71(10) . . ?
N1 C6 C5 122.67(12) . . ?
N1 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C6 C5 C4 120.05(12) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C2 C3 C4 119.63(12) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O8 H8 N1 0.91 1.68 2.5831(14) 170.2 .
C2 H2 O8 0.95 2.54 3.2379(18) 130.8 2_645

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.37
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.037
_database_code_depnum_ccdc_archive 'CCDC 1008279'
#######################################################################
#
#                 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_FUM3PIC

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_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           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                   9.805(2)
_cell_length_b                   4.8099(10)
_cell_length_c                   16.660(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.91(3)
_cell_angle_gamma                90.00
_cell_volume                     776.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1615
_cell_measurement_theta_min      4.21
_cell_measurement_theta_max      28.68

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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            3742
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.21
_diffrn_reflns_theta_max         28.68
_reflns_number_total             2005
_reflns_number_gt                1615
_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)+(0.0583P)²+0.1134P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2005
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1125
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_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
O8 O 0.93325(7) 0.64058(16) 0.59331(5) 0.0315(2) Uani 1 1 d . . .
O10 O 0.75782(8) 0.62912(17) 0.48949(5) 0.0343(2) Uani 1 1 d . . .
N1 N 0.80286(9) 0.26798(19) 0.66473(5) 0.0274(2) Uani 1 1 d . . .
C11 C 0.93935(10) 0.9489(2) 0.48428(6) 0.0264(2) Uani 1 1 d . . .
H11 H 0.8950 1.0238 0.4342 0.032 Uiso 1 1 calc R . .
C5 C 0.61576(10) -0.0589(2) 0.65546(7) 0.0284(2) Uani 1 1 d . . .
C4 C 0.66070(11) -0.1349(2) 0.73552(7) 0.0321(3) Uani 1 1 d . . .
H4 H 0.6123 -0.2738 0.7603 0.039 Uiso 1 1 calc R . .
C6 C 0.69137(11) 0.1464(2) 0.62331(6) 0.0277(2) Uani 1 1 d . . .
H6 H 0.6619 0.2033 0.5688 0.033 Uiso 1 1 calc R . .
C3 C 0.77581(11) -0.0094(2) 0.77952(7) 0.0329(3) Uani 1 1 d . . .
H3 H 0.8070 -0.0605 0.8344 0.039 Uiso 1 1 calc R . .
C9 C 0.86756(10) 0.7232(2) 0.52248(6) 0.0251(2) Uani 1 1 d . . .
C2 C 0.84420(11) 0.1916(2) 0.74196(7) 0.0293(2) Uani 1 1 d . . .
H2 H 0.9231 0.2785 0.7719 0.035 Uiso 1 1 calc R . .
C7 C 0.49243(13) -0.1882(3) 0.60416(8) 0.0435(3) Uani 1 1 d . . .
H7A H 0.4511 -0.3263 0.6364 0.065 Uiso 1 1 calc R . .
H7B H 0.5214 -0.2791 0.5569 0.065 Uiso 1 1 calc R . .
H7C H 0.4243 -0.0436 0.5857 0.065 Uiso 1 1 calc R . .
H1 H 0.8791 0.5025 0.6170 0.072(5) Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O8 0.0321(4) 0.0331(4) 0.0267(4) 0.0077(3) -0.0034(3) -0.0088(3)
O10 0.0300(4) 0.0405(5) 0.0301(4) 0.0030(3) -0.0028(3) -0.0113(3)
N1 0.0299(4) 0.0272(5) 0.0246(5) 0.0029(4) 0.0020(3) -0.0018(4)
C11 0.0296(5) 0.0264(5) 0.0223(5) 0.0027(4) 0.0008(4) -0.0022(4)
C5 0.0255(5) 0.0323(6) 0.0276(6) 0.0003(4) 0.0041(4) 0.0003(4)
C4 0.0314(5) 0.0351(6) 0.0310(6) 0.0075(5) 0.0085(4) -0.0014(5)
C6 0.0300(5) 0.0309(5) 0.0211(5) 0.0029(4) 0.0007(4) 0.0005(4)
C3 0.0354(6) 0.0389(6) 0.0232(5) 0.0068(4) 0.0011(4) 0.0022(5)
C9 0.0268(5) 0.0251(5) 0.0228(5) 0.0000(4) 0.0020(4) -0.0016(4)
C2 0.0300(5) 0.0315(5) 0.0248(5) 0.0006(4) -0.0006(4) 0.0004(4)
C7 0.0356(6) 0.0533(8) 0.0391(7) 0.0049(6) -0.0016(5) -0.0150(6)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O8 C9 1.3152(12) . ?
O8 H1 0.9715 . ?
O10 C9 1.2171(12) . ?
N1 C6 1.3338(14) . ?
N1 C2 1.3390(14) . ?
C11 C11 1.318(2) 3_776 ?
C11 C9 1.4893(14) . ?
C11 H11 0.9500 . ?
C5 C4 1.3874(16) . ?
C5 C6 1.3910(15) . ?
C5 C7 1.5032(16) . ?
C4 C3 1.3854(17) . ?
C4 H4 0.9500 . ?
C6 H6 0.9500 . ?
C3 C2 1.3805(16) . ?
C3 H3 0.9500 . ?
C2 H2 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O8 H1 110.4 . . ?
C6 N1 C2 118.60(9) . . ?
C11 C11 C9 123.99(12) 3_776 . ?
C11 C11 H11 118.0 3_776 . ?
C9 C11 H11 118.0 . . ?
C4 C5 C6 116.65(10) . . ?
C4 C5 C7 123.03(11) . . ?
C6 C5 C7 120.32(10) . . ?
C3 C4 C5 120.33(10) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N1 C6 C5 123.70(10) . . ?
N1 C6 H6 118.1 . . ?
C5 C6 H6 118.1 . . ?
C2 C3 C4 118.59(10) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
O10 C9 O8 124.66(10) . . ?
O10 C9 C11 121.42(9) . . ?
O8 C9 C11 113.92(8) . . ?
N1 C2 C3 122.12(10) . . ?
N1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O8 H1 N1 0.97 1.63 2.5948(12) 173.7 .
C2 H2 O8 0.95 2.55 3.2400(18) 129.9 2_746

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.68
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 1008280'
#######################################################################
#
#                 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_ADI4PIC

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H24 N2 O4'
_chemical_formula_weight         332.39

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   6.9477(14)
_cell_length_b                   7.1623(14)
_cell_length_c                   10.509(2)
_cell_angle_alpha                78.17(3)
_cell_angle_beta                 73.89(3)
_cell_angle_gamma                62.48(3)
_cell_volume                     443.76(15)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1917
_cell_measurement_theta_min      2.03
_cell_measurement_theta_max      28.36

_exptl_crystal_description       chunk
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             178
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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            8165
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         28.36
_reflns_number_total             2207
_reflns_number_gt                1917
_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)+(0.0637P)²+0.0549P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         2207
_refine_ls_number_parameters     219
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.1037
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.569
_refine_ls_shift/su_mean         0.172

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 0.1602(6) 0.1360(6) 0.8561(3) 0.0301(8) Uani 1 1 d . . .
C2 C 0.0713(8) 0.1714(8) 0.7519(4) 0.0341(10) Uani 1 1 d . . .
H2 H 0.0870 0.2744 0.6820 0.041 Uiso 1 1 calc R . .
C3 C -0.0452(8) 0.0609(7) 0.7421(4) 0.0339(10) Uani 1 1 d . . .
H3 H -0.1073 0.0901 0.6664 0.041 Uiso 1 1 calc R . .
C4 C -0.0701(7) -0.0887(6) 0.8409(4) 0.0302(10) Uani 1 1 d . . .
C5 C 0.0227(6) -0.1250(6) 0.9512(3) 0.0260(9) Uani 1 1 d . . .
H5 H 0.0086 -0.2268 1.0224 0.031 Uiso 1 1 calc R . .
C6 C 0.1366(7) -0.0085(7) 0.9546(4) 0.0303(9) Uani 1 1 d . . .
H6 H 0.1992 -0.0329 1.0295 0.036 Uiso 1 1 calc R . .
C7 C -0.1954(10) -0.2111(9) 0.8357(5) 0.0490(14) Uani 1 1 d . . .
H7A H -0.3542 -0.1291 0.8704 0.073 Uiso 1 1 calc R . .
H7B H -0.1414 -0.3463 0.8900 0.073 Uiso 1 1 calc R . .
H7C H -0.1720 -0.2373 0.7435 0.073 Uiso 1 1 calc R . .
O8 O 0.3713(5) 0.3437(5) 0.8991(2) 0.0323(8) Uani 1 1 d . . .
C9 C 0.4364(7) 0.2792(7) 1.0159(4) 0.0268(9) Uani 1 1 d . . .
O10 O 0.4010(6) 0.1424(6) 1.0933(3) 0.0432(9) Uani 1 1 d . . .
C11 C 0.5593(6) 0.3963(6) 1.0344(4) 0.0260(8) Uani 1 1 d . . .
H11A H 0.4589 0.5493 1.0338 0.031 Uiso 1 1 calc R . .
H11B H 0.6868 0.3767 0.9585 0.031 Uiso 1 1 calc R . .
C12 C 0.6443(7) 0.3215(6) 1.1641(4) 0.0271(8) Uani 1 1 d . . .
H12A H 0.5163 0.3530 1.2406 0.033 Uiso 1 1 calc R . .
H12B H 0.7347 0.1664 1.1686 0.033 Uiso 1 1 calc R . .
C13 C 0.7843(7) 0.4289(7) 1.1740(4) 0.0280(8) Uani 1 1 d . . .
H13A H 0.9117 0.3978 1.0972 0.034 Uiso 1 1 calc R . .
H13B H 0.6935 0.5839 1.1695 0.034 Uiso 1 1 calc R . .
C14 C 0.8700(7) 0.3572(7) 1.3006(4) 0.0317(9) Uani 1 1 d . . .
H14A H 0.7425 0.3744 1.3762 0.038 Uiso 1 1 calc R . .
H14B H 0.9705 0.2043 1.3003 0.038 Uiso 1 1 calc R . .
C15 C 0.9918(7) 0.4688(7) 1.3252(4) 0.0281(8) Uani 1 1 d . . .
O16 O 1.0266(5) 0.6059(5) 1.2473(3) 0.0367(8) Uani 1 1 d . . .
O17 O 1.0559(5) 0.4035(5) 1.4386(3) 0.0402(9) Uani 1 1 d . . .
N18 N 1.2657(6) 0.6114(6) 1.4822(3) 0.0319(8) Uani 1 1 d . . .
C19 C 1.3594(8) 0.5772(7) 1.5867(4) 0.0310(9) Uani 1 1 d . . .
H19 H 1.3439 0.4739 1.6564 0.037 Uiso 1 1 calc R . .
C20 C 1.4757(8) 0.6824(7) 1.5986(4) 0.0336(9) Uani 1 1 d . . .
H20 H 1.5375 0.6524 1.6745 0.040 Uiso 1 1 calc R . .
C21 C 1.5016(7) 0.8359(6) 1.4956(4) 0.0329(10) Uani 1 1 d . . .
C22 C 1.4062(8) 0.8702(7) 1.3896(4) 0.0384(11) Uani 1 1 d . . .
H22 H 1.4193 0.9718 1.3180 0.046 Uiso 1 1 calc R . .
C23 C 1.2927(8) 0.7589(7) 1.3866(4) 0.0330(10) Uani 1 1 d . . .
H23 H 1.2285 0.7877 1.3118 0.040 Uiso 1 1 calc R . .
C24 C 1.6234(9) 0.9582(8) 1.5030(5) 0.0473(14) Uani 1 1 d . . .
H24A H 1.5241 1.0762 1.5576 0.071 Uiso 1 1 calc R . .
H24B H 1.6740 1.0132 1.4132 0.071 Uiso 1 1 calc R . .
H24C H 1.7519 0.8652 1.5429 0.071 Uiso 1 1 calc R . .
H17 H 1.1180 0.4826 1.4563 0.057 Uiso 1 1 d R . .
H8 H 0.3039 0.2694 0.8872 0.057 Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0301(18) 0.0349(19) 0.0332(19) -0.0051(15) -0.0075(15) -0.0193(16)
C2 0.042(3) 0.037(2) 0.032(2) 0.0011(18) -0.0071(18) -0.026(2)
C3 0.045(3) 0.041(2) 0.0292(18) -0.0029(16) -0.0169(17) -0.025(2)
C4 0.032(2) 0.037(2) 0.031(2) -0.0052(18) -0.0123(16) -0.0181(19)
C5 0.032(2) 0.029(2) 0.0242(18) 0.0034(15) -0.0098(15) -0.0185(18)
C6 0.031(2) 0.033(2) 0.033(2) 0.0017(16) -0.0145(16) -0.0162(19)
C7 0.065(4) 0.057(3) 0.049(3) 0.002(2) -0.027(3) -0.040(3)
O8 0.0474(19) 0.0418(18) 0.0269(14) 0.0064(12) -0.0200(13) -0.0321(16)
C9 0.029(2) 0.034(2) 0.0213(18) -0.0004(15) -0.0070(14) -0.0173(19)
O10 0.057(2) 0.055(2) 0.0348(18) 0.0081(15) -0.0176(15) -0.038(2)
C11 0.031(2) 0.0310(18) 0.0257(17) 0.0026(14) -0.0157(15) -0.0186(17)
C12 0.028(2) 0.033(2) 0.0238(17) -0.0022(15) -0.0095(15) -0.0143(17)
C13 0.025(2) 0.034(2) 0.0293(19) -0.0062(16) -0.0027(15) -0.0169(18)
C14 0.027(2) 0.034(2) 0.034(2) -0.0042(17) -0.0019(15) -0.0147(18)
C15 0.025(2) 0.031(2) 0.030(2) -0.0035(15) -0.0089(15) -0.0108(18)
O16 0.049(2) 0.0466(19) 0.0312(16) 0.0109(13) -0.0196(14) -0.0342(17)
O17 0.047(2) 0.048(2) 0.0355(17) 0.0080(15) -0.0189(14) -0.0281(18)
N18 0.033(2) 0.035(2) 0.0290(18) -0.0012(15) -0.0085(15) -0.0152(17)
C19 0.037(2) 0.037(2) 0.0209(18) 0.0008(16) -0.0076(16) -0.0184(19)
C20 0.041(2) 0.039(2) 0.0250(17) 0.0047(16) -0.0100(16) -0.021(2)
C21 0.034(2) 0.029(2) 0.034(2) -0.0001(18) -0.0021(17) -0.0161(19)
C22 0.039(3) 0.032(2) 0.038(2) -0.0005(19) -0.0077(19) -0.012(2)
C23 0.036(2) 0.036(2) 0.0251(19) -0.0030(16) -0.0103(16) -0.011(2)
C24 0.062(4) 0.050(3) 0.051(3) 0.007(2) -0.018(2) -0.043(3)

_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 1.328(6) . ?
N1 C6 1.340(5) . ?
C2 C3 1.401(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.368(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.401(5) . ?
C4 C7 1.511(6) . ?
C5 C6 1.401(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
O8 C9 1.344(4) . ?
O8 H8 0.8989 . ?
C9 O10 1.211(5) . ?
C9 C11 1.513(5) . ?
C11 C12 1.533(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5271(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.505(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.501(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O16 1.214(5) . ?
C15 O17 1.308(5) . ?
O17 H17 0.9243 . ?
N18 C23 1.343(5) . ?
N18 C19 1.352(6) . ?
C19 C20 1.376(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.414(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.374(6) . ?
C21 C24 1.496(6) . ?
C22 C23 1.365(6) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 118.9(4) . . ?
N1 C2 C3 121.7(4) . . ?
N1 C2 H2 119.1 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 120.5(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 117.8(4) . . ?
C3 C4 C7 122.6(4) . . ?
C5 C4 C7 119.7(4) . . ?
C6 C5 C4 118.8(3) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
N1 C6 C5 122.3(3) . . ?
N1 C6 H6 118.9 . . ?
C5 C6 H6 118.8 . . ?
C4 C7 H7A 109.4 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 O8 H8 110.8 . . ?
O10 C9 O8 122.8(4) . . ?
O10 C9 C11 125.9(4) . . ?
O8 C9 C11 111.3(3) . . ?
C9 C11 C12 112.9(3) . . ?
C9 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C9 C11 H11B 109.0 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 111.6(2) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 112.5(3) . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C13 116.3(4) . . ?
C15 C14 H14A 108.2 . . ?
C13 C14 H14A 108.2 . . ?
C15 C14 H14B 108.2 . . ?
C13 C14 H14B 108.2 . . ?
H14A C14 H14B 107.4 . . ?
O16 C15 O17 123.7(4) . . ?
O16 C15 C14 123.1(4) . . ?
O17 C15 C14 113.3(4) . . ?
C15 O17 H17 112.3 . . ?
C23 N18 C19 115.4(4) . . ?
N18 C19 C20 124.2(4) . . ?
N18 C19 H19 117.9 . . ?
C20 C19 H19 117.9 . . ?
C19 C20 C21 118.8(4) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.6 . . ?
C22 C21 C20 116.9(4) . . ?
C22 C21 C24 121.6(4) . . ?
C20 C21 C24 121.6(4) . . ?
C23 C22 C21 120.3(4) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
N18 C23 C22 124.5(4) . . ?
N18 C23 H23 117.7 . . ?
C22 C23 H23 117.8 . . ?
C21 C24 H24A 109.4 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.4 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C19 H19 O8 0.95 2.56 3.370(5) 143.6 1_656
C2 H2 O17 0.95 2.57 3.376(5) 142.9 1_454
C5 H5 O16 0.95 2.43 3.307(5) 153.6 1_445
C22 H22 O10 0.95 2.43 3.317(6) 154.5 1_665
C23 H23 O16 0.95 2.59 3.285(6) 130.5 .
C6 H6 O10 0.95 2.55 3.261(6) 132.1 .
O8 H8 N1 0.90 1.79 2.688(4) 176.2 .
O17 H17 N18 0.92 1.76 2.684(5) 173.5 .

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.034
_database_code_depnum_ccdc_archive 'CCDC 1008281'
