# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1561493'
_audit_update_record             
;
2017-07-11 deposited with the CCDC.
2017-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 N3 O2'
_chemical_formula_sum            'C9 H9 N3 O2'
_chemical_formula_weight         191.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0040 0.0020 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0076 0.0040 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175'
O O 0.0132 0.0074 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   3.8441(3)
_cell_length_b                   14.0818(11)
_cell_length_c                   8.2393(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.091(5)
_cell_angle_gamma                90
_cell_volume                     437.68(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2635
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      29.82

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9898
_exptl_absorpt_correction_T_max  0.9987
_exptl_absorpt_process_details   'SADABS v2012/1 (Sheldrick)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
; 
loop mount with paratone
;


_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.7749
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         synchrotron
_diffrn_radiation_monochromator  'Si-<111> channel cut crystal'
_diffrn_measurement_device_type  'Bruker AXS APEXII CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6675
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.154
_diffrn_reflns_theta_max         29.952
_diffrn_reflns_theta_full        27.706
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             1900
_reflns_number_gt                1639
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.947
_reflns_Friedel_fraction_max     0.957
_reflns_Friedel_fraction_full    0.970

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;


_computing_data_collection       'Bruker APEX2 v2013.6.2'
_computing_cell_refinement       'Bruker SAINT v8.32B'
_computing_data_reduction        'Bruker SAINT v8.32B'
_computing_structure_solution    'Bruker SHELXTL v6.14'
_computing_structure_refinement  
"Bruker SHELXTL v6.14 & SHELXL-2014/7 (Sheldrick, 2014)'"
_computing_molecular_graphics    'Bruker SHELXTL v6.14'
_computing_publication_material  'Bruker SHELXTL v6.14'


_refine_special_details          ?


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+0.0806P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1900
_refine_ls_number_parameters     128
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.071
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4993(7) 0.40603(13) 0.4143(3) 0.0364(5) Uani 1 1 d . . . . .
O2 O 0.7383(5) 0.03224(13) 0.0212(2) 0.0268(5) Uani 1 1 d . . . . .
N1 N 0.5770(8) 0.56764(17) 0.2700(3) 0.0359(7) Uani 1 1 d . . . . .
N2 N 0.6239(7) 0.64408(18) 0.2029(3) 0.0309(6) Uani 1 1 d . . . . .
N3 N 0.6532(10) 0.71851(18) 0.1585(4) 0.0422(7) Uani 1 1 d . . . . .
C1 C 0.6259(7) 0.30133(18) 0.2101(3) 0.0223(6) Uani 1 1 d . . . . .
C2 C 0.5639(7) 0.22171(19) 0.3006(3) 0.0248(7) Uani 1 1 d . . . . .
H2 H 0.4986 0.2301 0.4052 0.030 Uiso 1 1 calc R U . . .
C3 C 0.5951(8) 0.1309(2) 0.2419(3) 0.0236(6) Uani 1 1 d . . . . .
H3 H 0.5493 0.0774 0.3048 0.028 Uiso 1 1 calc R U . . .
C4 C 0.6945(7) 0.11847(18) 0.0894(3) 0.0218(6) Uani 1 1 d . . . . .
C5 C 0.7571(8) 0.1972(2) -0.0034(3) 0.0250(7) Uani 1 1 d . . . . .
H5 H 0.8233 0.1887 -0.1077 0.030 Uiso 1 1 calc R U . . .
C6 C 0.7227(9) 0.2875(2) 0.0563(4) 0.0247(6) Uani 1 1 d . . . . .
H6 H 0.7652 0.3409 -0.0075 0.030 Uiso 1 1 calc R U . . .
C7 C 0.5832(8) 0.39655(19) 0.2796(4) 0.0251(6) Uani 1 1 d . . . . .
C8 C 0.6378(9) 0.48233(18) 0.1778(4) 0.0276(7) Uani 1 1 d . . . . .
H8A H 0.8823 0.4826 0.1561 0.033 Uiso 1 1 calc R U . . .
H8B H 0.4703 0.4807 0.0703 0.033 Uiso 1 1 calc R U . . .
C9 C 0.6698(9) -0.0502(2) 0.1117(4) 0.0291(7) Uani 1 1 d . . . . .
H9A H 0.7055 -0.1074 0.0491 0.044 Uiso 1 1 calc R U . . .
H9B H 0.4246 -0.0484 0.1290 0.044 Uiso 1 1 calc R U . . .
H9C H 0.8323 -0.0513 0.2191 0.044 Uiso 1 1 calc R U . . .


_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
O1 C7 1.221(4) . ?
O2 C4 1.362(3) . ?
O2 C9 1.431(3) . ?
N1 N2 1.239(3) . ?
N1 C8 1.464(4) . ?
N2 N3 1.123(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.401(4) . ?
C1 C7 1.479(4) . ?
C2 C3 1.381(3) . ?
C3 C4 1.393(4) . ?
C4 C5 1.394(4) . ?
C5 C6 1.378(4) . ?
C7 C8 1.508(4) . ?

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 O2 C9 117.3(2) . . ?
N2 N1 C8 115.4(2) . . ?
N3 N2 N1 171.3(3) . . ?
C2 C1 C6 118.4(2) . . ?
C2 C1 C7 118.6(2) . . ?
C6 C1 C7 123.0(2) . . ?
C3 C2 C1 121.5(2) . . ?
C2 C3 C4 119.4(3) . . ?
O2 C4 C3 124.2(2) . . ?
O2 C4 C5 115.8(2) . . ?
C3 C4 C5 120.1(3) . . ?
C6 C5 C4 120.0(2) . . ?
C5 C6 C1 120.7(2) . . ?
O1 C7 C1 121.3(2) . . ?
O1 C7 C8 120.5(2) . . ?
C1 C7 C8 118.2(2) . . ?
N1 C8 C7 108.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.2(4) . . . . ?
C7 C1 C2 C3 179.2(3) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C9 O2 C4 C3 1.4(4) . . . . ?
C9 O2 C4 C5 -178.8(2) . . . . ?
C2 C3 C4 O2 179.0(3) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
O2 C4 C5 C6 -179.4(3) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
C7 C1 C6 C5 -179.6(3) . . . . ?
C2 C1 C7 O1 0.8(4) . . . . ?
C6 C1 C7 O1 -179.8(3) . . . . ?
C2 C1 C7 C8 -177.8(3) . . . . ?
C6 C1 C7 C8 1.6(4) . . . . ?
N2 N1 C8 C7 177.8(3) . . . . ?
O1 C7 C8 N1 0.6(4) . . . . ?
C1 C7 C8 N1 179.2(3) . . . . ?

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.038

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_7
_database_code_depnum_ccdc_archive 'CCDC 1561494'
_audit_update_record             
;
2017-07-11 deposited with the CCDC.
2017-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 N O4'
_chemical_formula_sum            'C17 H17 N O4'
_chemical_formula_weight         299.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0040 0.0020 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0076 0.0040 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175'
O O 0.0132 0.0074 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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                   16.431(3)
_cell_length_b                   5.3912(9)
_cell_length_c                   16.311(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.010(3)
_cell_angle_gamma                90
_cell_volume                     1441.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3178
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      30.13

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.118
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9953
_exptl_absorpt_correction_T_max  0.9988
_exptl_absorpt_process_details   'SADABS v2012/1 (Sheldrick)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
; 
loop mount with paratone
;


_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.7749
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         synchrotron
_diffrn_radiation_monochromator  'Si-<111> channel cut crystal'
_diffrn_measurement_device_type  'Bruker AXS APEXII CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17437
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.355
_diffrn_reflns_theta_max         31.131
_diffrn_reflns_theta_full        27.706
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3525
_reflns_number_gt                2536
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2 v2013.6.2'
_computing_cell_refinement       'Bruker SAINT v8.32B'
_computing_data_reduction        'Bruker SAINT v8.32B'
_computing_structure_solution    'Bruker SHELXTL v6.14'
_computing_structure_refinement  
"Bruker SHELXTL v6.14 & SHELXL-2014/7 (Sheldrick, 2014)'"
_computing_molecular_graphics    'Bruker SHELXTL v6.14'
_computing_publication_material  'Bruker SHELXTL v6.14'


_refine_special_details          ?



_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0557P)²+0.3057P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3525
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1132
_refine_ls_wR_factor_gt          0.1017
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.19554(6) 0.44301(19) 0.47419(6) 0.0290(3) Uani 1 1 d . . . . .
O2 O 0.51607(6) 0.7625(2) 0.68144(7) 0.0350(3) Uani 1 1 d . . . . .
O3 O 0.69870(6) 0.0806(2) 0.67762(7) 0.0362(3) Uani 1 1 d . . . . .
O4 O 0.99732(6) 0.56572(19) 0.87889(6) 0.0295(3) Uani 1 1 d . . . . .
N1 N 0.64245(7) 0.4582(2) 0.68567(8) 0.0285(3) Uani 1 1 d . . . . .
H1 H 0.6427(10) 0.619(3) 0.6967(10) 0.034 Uiso 1 1 d . U . . .
C1 C 0.17689(9) 0.2314(3) 0.42378(9) 0.0310(3) Uani 1 1 d . . . . .
H1A H 0.1217 0.2484 0.3974 0.047 Uiso 1 1 calc R U . . .
H1B H 0.1798 0.0814 0.4578 0.047 Uiso 1 1 calc R U . . .
H1C H 0.2163 0.2191 0.3815 0.047 Uiso 1 1 calc R U . . .
C2 C 0.27149(8) 0.4545(3) 0.51354(8) 0.0230(3) Uani 1 1 d . . . . .
C3 C 0.33270(8) 0.2796(3) 0.50521(9) 0.0252(3) Uani 1 1 d . . . . .
H3 H 0.3235 0.1399 0.4703 0.030 Uiso 1 1 calc R U . . .
C4 C 0.40762(8) 0.3137(3) 0.54910(9) 0.0260(3) Uani 1 1 d . . . . .
H4 H 0.4494 0.1938 0.5445 0.031 Uiso 1 1 calc R U . . .
C5 C 0.42274(8) 0.5193(3) 0.59946(8) 0.0224(3) Uani 1 1 d . . . . .
C6 C 0.35990(8) 0.6909(3) 0.60679(9) 0.0262(3) Uani 1 1 d . . . . .
H6 H 0.3689 0.8318 0.6412 0.031 Uiso 1 1 calc R U . . .
C7 C 0.28515(8) 0.6581(3) 0.56474(9) 0.0278(3) Uani 1 1 d . . . . .
H7 H 0.2428 0.7751 0.5708 0.033 Uiso 1 1 calc R U . . .
C8 C 0.50246(8) 0.5690(3) 0.64450(8) 0.0244(3) Uani 1 1 d . . . . .
C9 C 0.56757(8) 0.3725(3) 0.64287(9) 0.0263(3) Uani 1 1 d . . . . .
H9A H 0.5488 0.2195 0.6694 0.032 Uiso 1 1 calc R U . . .
H9B H 0.5776 0.3325 0.5852 0.032 Uiso 1 1 calc R U . . .
C10 C 0.70430(8) 0.2984(3) 0.70048(9) 0.0260(3) Uani 1 1 d . . . . .
C11 C 0.77993(8) 0.3917(3) 0.74673(8) 0.0234(3) Uani 1 1 d . . . . .
C12 C 0.85082(8) 0.2516(3) 0.74128(9) 0.0272(3) Uani 1 1 d . . . . .
H12 H 0.8498 0.1092 0.7069 0.033 Uiso 1 1 calc R U . . .
C13 C 0.92200(8) 0.3173(3) 0.78504(9) 0.0274(3) Uani 1 1 d . . . . .
H13 H 0.9701 0.2224 0.7799 0.033 Uiso 1 1 calc R U . . .
C14 C 0.92393(8) 0.5219(3) 0.83672(8) 0.0232(3) Uani 1 1 d . . . . .
C15 C 0.85431(8) 0.6672(3) 0.84243(9) 0.0244(3) Uani 1 1 d . . . . .
H15 H 0.8555 0.8090 0.8771 0.029 Uiso 1 1 calc R U . . .
C16 C 0.78298(8) 0.6010(3) 0.79657(8) 0.0242(3) Uani 1 1 d . . . . .
H16 H 0.7356 0.7006 0.7994 0.029 Uiso 1 1 calc R U . . .
C17 C 1.00385(9) 0.7771(3) 0.93152(10) 0.0335(4) Uani 1 1 d . . . . .
H17A H 1.0599 0.7905 0.9560 0.050 Uiso 1 1 calc R U . . .
H17B H 0.9662 0.7591 0.9752 0.050 Uiso 1 1 calc R U . . .
H17C H 0.9900 0.9270 0.8995 0.050 Uiso 1 1 calc R U . . .


_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
O1 C2 1.3642(15) . ?
O1 C1 1.4269(17) . ?
O2 C8 1.2178(17) . ?
O3 C10 1.2333(18) . ?
O4 C14 1.3664(15) . ?
O4 C17 1.4264(18) . ?
N1 C10 1.3414(18) . ?
N1 C9 1.4473(17) . ?
C2 C7 1.388(2) . ?
C2 C3 1.3922(19) . ?
C3 C4 1.3922(18) . ?
C4 C5 1.3913(19) . ?
C5 C6 1.3978(19) . ?
C5 C8 1.4808(18) . ?
C6 C7 1.3756(19) . ?
C8 C9 1.507(2) . ?
C10 C11 1.4951(18) . ?
C11 C16 1.389(2) . ?
C11 C12 1.3962(19) . ?
C12 C13 1.3734(19) . ?
C13 C14 1.387(2) . ?
C14 C15 1.3948(19) . ?
C15 C16 1.3920(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 117.39(11) . . ?
C14 O4 C17 117.89(11) . . ?
C10 N1 C9 119.31(13) . . ?
O1 C2 C7 115.04(12) . . ?
O1 C2 C3 124.51(13) . . ?
C7 C2 C3 120.45(12) . . ?
C2 C3 C4 118.63(13) . . ?
C5 C4 C3 121.59(13) . . ?
C4 C5 C6 118.37(12) . . ?
C4 C5 C8 123.52(12) . . ?
C6 C5 C8 118.09(12) . . ?
C7 C6 C5 120.74(13) . . ?
C6 C7 C2 120.20(13) . . ?
O2 C8 C5 121.74(13) . . ?
O2 C8 C9 120.33(12) . . ?
C5 C8 C9 117.94(12) . . ?
N1 C9 C8 110.34(12) . . ?
O3 C10 N1 121.15(13) . . ?
O3 C10 C11 120.99(13) . . ?
N1 C10 C11 117.85(13) . . ?
C16 C11 C12 118.71(12) . . ?
C16 C11 C10 124.28(13) . . ?
C12 C11 C10 116.96(13) . . ?
C13 C12 C11 120.74(13) . . ?
C12 C13 C14 120.23(13) . . ?
O4 C14 C13 115.17(12) . . ?
O4 C14 C15 124.63(13) . . ?
C13 C14 C15 120.20(12) . . ?
C16 C15 C14 118.93(13) . . ?
C11 C16 C15 121.14(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 C2 C7 -177.11(13) . . . . ?
C1 O1 C2 C3 2.7(2) . . . . ?
O1 C2 C3 C4 -179.93(13) . . . . ?
C7 C2 C3 C4 -0.1(2) . . . . ?
C2 C3 C4 C5 -1.1(2) . . . . ?
C3 C4 C5 C6 1.4(2) . . . . ?
C3 C4 C5 C8 -177.31(14) . . . . ?
C4 C5 C6 C7 -0.5(2) . . . . ?
C8 C5 C6 C7 178.31(14) . . . . ?
C5 C6 C7 C2 -0.7(2) . . . . ?
O1 C2 C7 C6 -179.15(13) . . . . ?
C3 C2 C7 C6 1.0(2) . . . . ?
C4 C5 C8 O2 172.57(14) . . . . ?
C6 C5 C8 O2 -6.1(2) . . . . ?
C4 C5 C8 C9 -6.9(2) . . . . ?
C6 C5 C8 C9 174.41(13) . . . . ?
C10 N1 C9 C8 171.21(13) . . . . ?
O2 C8 C9 N1 -2.85(19) . . . . ?
C5 C8 C9 N1 176.60(12) . . . . ?
C9 N1 C10 O3 0.7(2) . . . . ?
C9 N1 C10 C11 -178.47(13) . . . . ?
O3 C10 C11 C16 -158.42(14) . . . . ?
N1 C10 C11 C16 20.7(2) . . . . ?
O3 C10 C11 C12 19.0(2) . . . . ?
N1 C10 C11 C12 -161.91(13) . . . . ?
C16 C11 C12 C13 0.8(2) . . . . ?
C10 C11 C12 C13 -176.77(14) . . . . ?
C11 C12 C13 C14 1.3(2) . . . . ?
C17 O4 C14 C13 178.45(13) . . . . ?
C17 O4 C14 C15 -1.1(2) . . . . ?
C12 C13 C14 O4 178.24(13) . . . . ?
C12 C13 C14 C15 -2.2(2) . . . . ?
O4 C14 C15 C16 -179.47(13) . . . . ?
C13 C14 C15 C16 1.0(2) . . . . ?
C12 C11 C16 C15 -2.0(2) . . . . ?
C10 C11 C16 C15 175.38(13) . . . . ?
C14 C15 C16 C11 1.1(2) . . . . ?

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
N1 H1 O3 0.886(18) 2.679(18) 3.4854(18) 151.9(14) 1_565

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.041

