

data_global
#TrackingRef 'web_deposit_cif_file_0_matthewcdavis_1364340814.TG_MD_52_Resveratrol_1_0m.cif'

_audit_creation_method           'APEX2 v2012.4-3'

data_I
#TrackingRef 'web_deposit_cif_file_0_matthewcdavis_1364340814.TG_MD_52_Resveratrol_1_0m.cif'

_chemical_name_systematic        ?
_chemical_name_common            'resveratrol tricyanate'
_chemical_formula_moiety         'C17 H9 N3 O3'
_chemical_formula_sum            'C17 H9 N3 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         303.27

_chemical_melting_point          438

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   3.9559(3)
_cell_length_b                   20.3303(14)
_cell_length_c                   18.2471(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.0410(10)
_cell_angle_gamma                90
_cell_volume                     1461.84(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2074
_cell_measurement_theta_min      2.2409
_cell_measurement_theta_max      21.6994
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Rod
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624

_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       CCD

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            16001
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_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.
;

_reflns_number_total             2586
_reflns_number_gt                1496
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1208
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_number_reflns         2586
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0366P)²+0.6691P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.175
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O3 0.1835(5) 0.41504(9) 0.20019(10) 0.0675(5) Uani d . 1 . .
O O2 1.2359(6) 0.89763(10) 0.12367(10) 0.0778(6) Uani d . 1 . .
O O1 0.9269(6) 0.84909(10) -0.12954(10) 0.0821(6) Uani d . 1 . .
N N3 -0.1877(7) 0.35026(13) 0.11570(16) 0.0844(8) Uani d . 1 . .
N N2 1.5274(8) 0.99781(15) 0.09631(15) 0.0954(9) Uani d . 1 . .
N N1 0.6659(9) 0.77790(16) -0.22392(16) 0.1097(11) Uani d . 1 . .
C C17 -0.0118(8) 0.38071(14) 0.15412(17) 0.0634(7) Uani d . 1 . .
C C14 0.3046(6) 0.47601(12) 0.17481(14) 0.0508(6) Uani d . 1 . .
C C15 0.2511(7) 0.49541(13) 0.10340(14) 0.0597(7) Uani d . 1 . .
H H8 0.1366 0.4685 0.0682 0.072 Uiso calc R 1 . .
C C16 0.3728(7) 0.55670(14) 0.08461(15) 0.0631(7) Uani d . 1 . .
H H9 0.3369 0.5713 0.0363 0.076 Uiso calc R 1 . .
C C11 0.5480(6) 0.59657(12) 0.13731(16) 0.0567(7) Uani d . 1 . .
C C2 0.6848(7) 0.66221(14) 0.11995(16) 0.0679(8) Uani d . 1 . .
H H2 0.7978 0.6855 0.1585 0.081 Uiso calc R 1 . .
C C1 0.6609(7) 0.68951(14) 0.05659(16) 0.0660(8) Uani d . 1 . .
H H1 0.5435 0.6665 0.0183 0.079 Uiso calc R 1 . .
C C3 0.8042(6) 0.75502(12) 0.03826(15) 0.0562(7) Uani d . 1 . .
C C8 0.9554(7) 0.79810(13) 0.09023(15) 0.0589(7) Uani d . 1 . .
H H5 0.9689 0.7877 0.14 0.071 Uiso calc R 1 . .
C C7 1.0851(6) 0.85647(13) 0.06675(14) 0.0553(7) Uani d . 1 . .
C C10 1.3881(8) 0.95092(18) 0.10674(16) 0.0695(8) Uani d . 1 . .
C C12 0.6008(7) 0.57331(14) 0.20777(15) 0.0618(7) Uani d . 1 . .
H H6 0.7228 0.5988 0.2432 0.074 Uiso calc R 1 . .
C C13 0.4791(7) 0.51366(13) 0.22729(15) 0.0615(7) Uani d . 1 . .
H H7 0.5143 0.4989 0.2756 0.074 Uiso calc R 1 . .
C C4 0.7891(7) 0.77208(12) -0.03502(14) 0.0560(7) Uani d . 1 . .
H H3 0.6863 0.7442 -0.0707 0.067 Uiso calc R 1 . .
C C5 0.9264(7) 0.83024(12) -0.05451(14) 0.0559(7) Uani d . 1 . .
C C9 0.7856(9) 0.80989(16) -0.17854(18) 0.0779(9) Uani d . 1 . .
C C6 1.0774(6) 0.87502(13) -0.00534(14) 0.0556(7) Uani d . 1 . .
H H4 1.167 0.9147 -0.02 0.067 Uiso calc R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O3 C17 . 1.295(3) ?
O3 C14 . 1.421(3) ?
O2 C10 . 1.290(4) ?
O2 C7 . 1.423(3) ?
O1 C9 . 1.288(4) ?
O1 C5 . 1.422(3) ?
N3 C17 . 1.128(3) ?
N2 C10 . 1.126(4) ?
N1 C9 . 1.124(4) ?
C14 C15 . 1.360(3) ?
C14 C13 . 1.365(3) ?
C15 C16 . 1.390(3) ?
C15 H8 . 0.93 ?
C16 C11 . 1.395(4) ?
C16 H9 . 0.93 ?
C11 C12 . 1.369(4) ?
C11 C2 . 1.485(4) ?
C2 C1 . 1.278(4) ?
C2 H2 . 0.93 ?
C1 C3 . 1.497(4) ?
C1 H1 . 0.93 ?
C3 C4 . 1.378(3) ?
C3 C8 . 1.387(4) ?
C8 C7 . 1.376(4) ?
C8 H5 . 0.93 ?
C7 C6 . 1.366(3) ?
C12 C13 . 1.364(4) ?
C12 H6 . 0.93 ?
C13 H7 . 0.93 ?
C4 C5 . 1.361(3) ?
C4 H3 . 0.93 ?
C5 C6 . 1.377(3) ?
C6 H4 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C17 O3 C14 . . 117.2(2) ?
C10 O2 C7 . . 119.6(2) ?
C9 O1 C5 . . 117.7(2) ?
N3 C17 O3 . . 177.9(3) ?
C15 C14 C13 . . 122.4(2) ?
C15 C14 O3 . . 122.4(2) ?
C13 C14 O3 . . 115.1(2) ?
C14 C15 C16 . . 117.9(2) ?
C14 C15 H8 . . 121.0 ?
C16 C15 H8 . . 121.0 ?
C15 C16 C11 . . 120.9(2) ?
C15 C16 H9 . . 119.6 ?
C11 C16 H9 . . 119.6 ?
C12 C11 C16 . . 118.2(2) ?
C12 C11 C2 . . 118.9(3) ?
C16 C11 C2 . . 122.9(3) ?
C1 C2 C11 . . 125.7(3) ?
C1 C2 H2 . . 117.1 ?
C11 C2 H2 . . 117.1 ?
C2 C1 C3 . . 126.1(3) ?
C2 C1 H1 . . 117.0 ?
C3 C1 H1 . . 117.0 ?
C4 C3 C8 . . 118.9(2) ?
C4 C3 C1 . . 117.1(2) ?
C8 C3 C1 . . 123.9(3) ?
C7 C8 C3 . . 118.8(2) ?
C7 C8 H5 . . 120.6 ?
C3 C8 H5 . . 120.6 ?
C6 C7 C8 . . 124.1(2) ?
C6 C7 O2 . . 120.8(2) ?
C8 C7 O2 . . 115.1(2) ?
N2 C10 O2 . . 175.9(3) ?
C13 C12 C11 . . 121.6(3) ?
C13 C12 H6 . . 119.2 ?
C11 C12 H6 . . 119.2 ?
C12 C13 C14 . . 118.9(3) ?
C12 C13 H7 . . 120.5 ?
C14 C13 H7 . . 120.5 ?
C5 C4 C3 . . 119.2(2) ?
C5 C4 H3 . . 120.4 ?
C3 C4 H3 . . 120.4 ?
C4 C5 C6 . . 124.3(2) ?
C4 C5 O1 . . 121.3(2) ?
C6 C5 O1 . . 114.3(2) ?
N1 C9 O1 . . 176.5(3) ?
C7 C6 C5 . . 114.6(2) ?
C7 C6 H4 . . 122.7 ?
C5 C6 H4 . . 122.7 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C14 O3 C17 N3 . . . . -142.(9) ?
C17 O3 C14 C15 . . . . -6.8(4) ?
C17 O3 C14 C13 . . . . 173.3(2) ?
C13 C14 C15 C16 . . . . -1.7(4) ?
O3 C14 C15 C16 . . . . 178.4(2) ?
C14 C15 C16 C11 . . . . 0.8(4) ?
C15 C16 C11 C12 . . . . 0.9(4) ?
C15 C16 C11 C2 . . . . 179.6(2) ?
C12 C11 C2 C1 . . . . 178.5(3) ?
C16 C11 C2 C1 . . . . -0.2(4) ?
C11 C2 C1 C3 . . . . -178.6(2) ?
C2 C1 C3 C4 . . . . 171.9(3) ?
C2 C1 C3 C8 . . . . -6.7(4) ?
C4 C3 C8 C7 . . . . 0.0(4) ?
C1 C3 C8 C7 . . . . 178.6(2) ?
C3 C8 C7 C6 . . . . -0.5(4) ?
C3 C8 C7 O2 . . . . -179.9(2) ?
C10 O2 C7 C6 . . . . -4.9(4) ?
C10 O2 C7 C8 . . . . 174.5(3) ?
C7 O2 C10 N2 . . . . -172.(5) ?
C16 C11 C12 C13 . . . . -1.8(4) ?
C2 C11 C12 C13 . . . . 179.4(2) ?
C11 C12 C13 C14 . . . . 1.0(4) ?
C15 C14 C13 C12 . . . . 0.8(4) ?
O3 C14 C13 C12 . . . . -179.3(2) ?
C8 C3 C4 C5 . . . . 0.8(4) ?
C1 C3 C4 C5 . . . . -177.8(2) ?
C3 C4 C5 C6 . . . . -1.3(4) ?
C3 C4 C5 O1 . . . . 177.9(2) ?
C9 O1 C5 C4 . . . . 1.6(4) ?
C9 O1 C5 C6 . . . . -179.1(3) ?
C5 O1 C9 N1 . . . . 180.(100) ?
C8 C7 C6 C5 . . . . 0.1(4) ?
O2 C7 C6 C5 . . . . 179.5(2) ?
C4 C5 C6 C7 . . . . 0.8(4) ?
O1 C5 C6 C7 . . . . -178.5(2) ?


data_global
#TrackingRef 'web_deposit_cif_file_0_matthewcdavis_1364340814.TG_MD_52_Resveratrol_1_0m.cif'

_audit_creation_method           'APEX2 v2012.4-3'


# Attachment 'web_deposit_cif_file_1_matthewcdavis_1364340814.TG_MD_1871_90B_1_0m.cif'

data_II
#TrackingRef 'web_deposit_cif_file_1_matthewcdavis_1364340814.TG_MD_1871_90B_1_0m.cif'

_chemical_name_systematic        ?
_chemical_name_common            'dihydroresveratrol tricyanate'
_chemical_formula_moiety         'C17 H11 N3 O3'
_chemical_formula_sum            'C17 H11 N3 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         305.29

_chemical_melting_point          391

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.4993(2)
_cell_length_b                   19.1442(8)
_cell_length_c                   17.7080(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.7330(10)
_cell_angle_gamma                90
_cell_volume                     1522.05(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632

_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
;
_exptl_absorpt_correction_T_min  .6632
_exptl_absorpt_correction_T_max  .7460

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       CCD

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            16429
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_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.
;

_reflns_number_total             2686
_reflns_number_gt                1979
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1164
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_number_reflns         2686
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0532P)²+0.3013P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.099
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0058(17)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.5613(4) 1.08035(8) 0.30300(7) 0.0863(5) Uani d . 1 . .
O O2 0.5450(4) 0.66162(8) 0.62381(7) 0.0868(5) Uani d . 1 . .
O O3 0.6098(3) 0.58374(7) 0.36942(7) 0.0752(4) Uani d . 1 . .
N N1 -0.7991(5) 1.15169(11) 0.39360(13) 0.1075(7) Uani d . 1 . .
C C15 0.2978(4) 0.67800(8) 0.39503(10) 0.0545(4) Uani d . 1 . .
H H15 0.2493 0.6802 0.3432 0.065 Uiso calc R 1 . .
C C14 0.4931(4) 0.62824(8) 0.42457(9) 0.0519(4) Uani d . 1 . .
C C7 -0.6853(5) 1.11776(11) 0.35208(12) 0.0758(6) Uani d . 1 . .
C C4 -0.3871(4) 1.02195(9) 0.32975(10) 0.0596(5) Uani d . 1 . .
C C3 -0.2687(5) 0.98225(11) 0.27539(11) 0.0792(6) Uani d . 1 . .
H H2 -0.3048 0.993 0.2244 0.095 Uiso calc R 1 . .
C C2 -0.0941(4) 0.92572(10) 0.29764(11) 0.0712(5) Uani d . 1 . .
H H1 -0.0114 0.8984 0.261 0.085 Uiso calc R 1 . .
C C1 -0.0395(4) 0.90889(8) 0.37270(10) 0.0528(4) Uani d . 1 . .
C C8 0.1525(4) 0.84753(9) 0.39775(11) 0.0599(5) Uani d . 1 . .
H H5 0.272 0.8603 0.4432 0.072 Uiso calc R 1 . .
H H6 0.2873 0.8371 0.3587 0.072 Uiso calc R 1 . .
C C9 -0.0254(4) 0.78241(9) 0.41359(11) 0.0610(5) Uani d . 1 . .
H H7 -0.17 0.7932 0.4502 0.073 Uiso calc R 1 . .
H H8 -0.133 0.7671 0.3673 0.073 Uiso calc R 1 . .
C C10 0.1752(3) 0.72464(8) 0.44377(10) 0.0526(4) Uani d . 1 . .
C C11 0.2537(4) 0.71994(9) 0.52092(10) 0.0584(5) Uani d . 1 . .
H H9 0.1737 0.7508 0.5548 0.07 Uiso calc R 1 . .
C C12 0.4504(4) 0.66926(9) 0.54625(9) 0.0566(4) Uani d . 1 . .
C C16 0.4246(6) 0.70002(12) 0.67254(12) 0.0842(7) Uani d . 1 . .
N N2 0.3288(6) 0.73176(13) 0.71842(12) 0.1255(9) Uani d . 1 . .
C C5 -0.3428(4) 1.00722(9) 0.40431(10) 0.0614(5) Uani d . 1 . .
H H3 -0.4277 1.0347 0.4405 0.074 Uiso calc R 1 . .
C C6 -0.1676(4) 0.95016(9) 0.42519(10) 0.0613(5) Uani d . 1 . .
H H4 -0.1356 0.9394 0.4763 0.074 Uiso calc R 1 . .
C C13 0.5760(4) 0.62155(9) 0.49995(9) 0.0547(4) Uani d . 1 . .
H H10 0.7076 0.5872 0.5185 0.066 Uiso calc R 1 . .
C C17 0.7905(5) 0.53450(10) 0.39037(10) 0.0646(5) Uani d . 1 . .
N N3 0.9506(5) 0.49074(11) 0.40316(11) 0.0988(7) Uani d . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.282(3) ?
O1 C4 . 1.428(2) ?
O2 C16 . 1.280(3) ?
O2 C12 . 1.419(2) ?
O3 C17 . 1.284(2) ?
O3 C14 . 1.4218(19) ?
N1 C7 . 1.129(3) ?
C15 C14 . 1.376(2) ?
C15 C10 . 1.382(2) ?
C15 H15 . 0.93 ?
C14 C13 . 1.368(2) ?
C4 C5 . 1.352(2) ?
C4 C3 . 1.362(3) ?
C3 C2 . 1.380(3) ?
C3 H2 . 0.93 ?
C2 C1 . 1.374(2) ?
C2 H1 . 0.93 ?
C1 C6 . 1.375(2) ?
C1 C8 . 1.507(2) ?
C8 C9 . 1.517(2) ?
C8 H5 . 0.97 ?
C8 H6 . 0.97 ?
C9 C10 . 1.503(2) ?
C9 H7 . 0.97 ?
C9 H8 . 0.97 ?
C10 C11 . 1.392(2) ?
C11 C12 . 1.369(2) ?
C11 H9 . 0.93 ?
C12 C13 . 1.373(2) ?
C16 N2 . 1.123(3) ?
C5 C6 . 1.383(2) ?
C5 H3 . 0.93 ?
C6 H4 . 0.93 ?
C13 H10 . 0.93 ?
C17 N3 . 1.118(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O1 C4 . . 117.79(15) ?
C16 O2 C12 . . 118.67(16) ?
C17 O3 C14 . . 119.79(14) ?
C14 C15 C10 . . 118.77(15) ?
C14 C15 H15 . . 120.6 ?
C10 C15 H15 . . 120.6 ?
C13 C14 C15 . . 124.21(15) ?
C13 C14 O3 . . 121.64(14) ?
C15 C14 O3 . . 114.14(14) ?
N1 C7 O1 . . 178.0(2) ?
C5 C4 C3 . . 122.29(16) ?
C5 C4 O1 . . 121.99(16) ?
C3 C4 O1 . . 115.72(15) ?
C4 C3 C2 . . 118.53(17) ?
C4 C3 H2 . . 120.7 ?
C2 C3 H2 . . 120.7 ?
C1 C2 C3 . . 121.52(17) ?
C1 C2 H1 . . 119.2 ?
C3 C2 H1 . . 119.2 ?
C2 C1 C6 . . 117.56(16) ?
C2 C1 C8 . . 122.02(16) ?
C6 C1 C8 . . 120.41(16) ?
C1 C8 C9 . . 113.31(14) ?
C1 C8 H5 . . 108.9 ?
C9 C8 H5 . . 108.9 ?
C1 C8 H6 . . 108.9 ?
C9 C8 H6 . . 108.9 ?
H5 C8 H6 . . 107.7 ?
C10 C9 C8 . . 111.02(13) ?
C10 C9 H7 . . 109.4 ?
C8 C9 H7 . . 109.4 ?
C10 C9 H8 . . 109.4 ?
C8 C9 H8 . . 109.4 ?
H7 C9 H8 . . 108.0 ?
C15 C10 C11 . . 119.03(15) ?
C15 C10 C9 . . 120.55(16) ?
C11 C10 C9 . . 120.31(16) ?
C12 C11 C10 . . 119.00(16) ?
C12 C11 H9 . . 120.5 ?
C10 C11 H9 . . 120.5 ?
C11 C12 C13 . . 123.92(16) ?
C11 C12 O2 . . 122.48(15) ?
C13 C12 O2 . . 113.59(15) ?
N2 C16 O2 . . 176.0(3) ?
C4 C5 C6 . . 118.09(16) ?
C4 C5 H3 . . 121.0 ?
C6 C5 H3 . . 121.0 ?
C1 C6 C5 . . 121.99(16) ?
C1 C6 H4 . . 119.0 ?
C5 C6 H4 . . 119.0 ?
C14 C13 C12 . . 115.06(15) ?
C14 C13 H10 . . 122.5 ?
C12 C13 H10 . . 122.5 ?
N3 C17 O3 . . 174.9(2) ?




