# Electronic Supplementary Material (ESI) for ChemComm.
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1544055'
_audit_update_record             
;
2017-04-14 deposited with the CCDC.
2017-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 N2 O5'
_chemical_formula_weight         262.22

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   3.748(8)
_cell_length_b                   12.14(3)
_cell_length_c                   26.33(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1198(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2282
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      33.4

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.644

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            9366
_diffrn_reflns_av_unetI/netI     0.1032
_diffrn_reflns_av_R_equivalents  0.1615
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.547
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2239
_reflns_number_gt                1709
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.631
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXL-14 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-14 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1498P)²+0.7180P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 438 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2239
_refine_ls_number_parameters     180
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1218
_refine_ls_R_factor_gt           0.0985
_refine_ls_wR_factor_ref         0.2934
_refine_ls_wR_factor_gt          0.2656
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_restrained_S_all      1.166
_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_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
O5 O 0.866(5) 0.7475(7) 0.0350(3) 0.105(4) Uani 1 1 d D . . . .
C003 C 0.534(2) 0.1281(6) 0.1006(3) 0.0336(17) Uani 1 1 d . . . . .
C004 C 0.420(2) 0.0311(7) 0.1309(3) 0.0321(17) Uani 1 1 d . . . . .
C005 C 0.270(3) 0.0431(7) 0.1791(3) 0.040(2) Uani 1 1 d . . . . .
H005 H 0.2245 0.1144 0.1925 0.049 Uiso 1 1 calc R U . . .
C006 C 0.246(2) -0.1502(7) 0.1863(3) 0.0363(18) Uani 1 1 d . . . . .
C007 C 0.189(3) -0.0487(7) 0.2069(3) 0.0395(19) Uani 1 1 d . . . . .
H007 H 0.0945 -0.0418 0.2402 0.047 Uiso 1 1 calc R U . . .
C008 C 0.464(2) 0.3574(7) 0.0547(3) 0.0396(19) Uani 1 1 d . . . . .
H008 H 0.3685 0.3078 0.0303 0.047 Uiso 1 1 calc R U . . .
C010 C 0.523(2) 0.3252(6) 0.1041(3) 0.0337(17) Uani 1 1 d . . . . .
C011 C 0.483(2) -0.0730(7) 0.1104(3) 0.0355(18) Uani 1 1 d . . . . .
H011 H 0.5869 -0.0802 0.0777 0.043 Uiso 1 1 calc R U . . .
C012 C 0.676(3) 0.3991(7) 0.1381(3) 0.043(2) Uani 1 1 d . . . . .
H012 H 0.7284 0.3780 0.1721 0.051 Uiso 1 1 calc R U . . .
C014 C 0.392(2) -0.1662(7) 0.1381(3) 0.038(2) Uani 1 1 d . . . . .
H014 H 0.4274 -0.2381 0.1248 0.046 Uiso 1 1 calc R U . . .
C017 C 0.747(3) 0.5033(7) 0.1209(3) 0.049(2) Uani 1 1 d . . . . .
H017 H 0.8438 0.5548 0.1444 0.059 Uiso 1 1 calc R U . . .
C018 C 0.548(3) 0.4647(7) 0.0420(3) 0.045(2) Uani 1 1 d . . . . .
H018 H 0.5004 0.4880 0.0083 0.054 Uiso 1 1 calc R U . . .
N1 N 0.691(2) 0.5373(6) 0.0734(3) 0.0486(19) Uani 1 1 d . . . . .
N2 N 0.155(2) -0.2488(6) 0.2168(2) 0.047(2) Uani 1 1 d . . . . .
O1 O 0.4254(17) 0.2241(5) 0.12387(18) 0.0420(15) Uani 1 1 d . . . . .
O2 O 0.708(2) 0.1273(5) 0.0623(2) 0.0512(17) Uani 1 1 d . . . . .
O3 O -0.026(2) -0.2344(5) 0.2552(2) 0.059(2) Uani 1 1 d . . . . .
O4 O 0.258(3) -0.3399(5) 0.2020(2) 0.064(2) Uani 1 1 d . . . . .
H5A H 0.80(5) 0.689(8) 0.051(5) 0.13(6) Uiso 1 1 d D . . . .
H5C H 1.01(3) 0.738(10) 0.009(3) 0.07(4) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 H5A 0.86(3) . ?
O5 H5C 0.87(3) . ?
C003 O2 1.202(9) . ?
C003 O1 1.379(9) . ?
C003 C004 1.484(10) . ?
C004 C011 1.394(11) . ?
C004 C005 1.397(11) . ?
C005 C007 1.367(11) . ?
C005 H005 0.9500 . ?
C006 C007 1.363(11) . ?
C006 C014 1.394(11) . ?
C006 N2 1.482(10) . ?
C007 H007 0.9500 . ?
C008 C010 1.376(11) . ?
C008 C018 1.382(12) . ?
C008 H008 0.9500 . ?
C010 O1 1.382(10) . ?
C010 C012 1.392(12) . ?
C011 C014 1.389(12) . ?
C011 H011 0.9500 . ?
C012 C017 1.371(13) . ?
C012 H012 0.9500 . ?
C014 H014 0.9500 . ?
C017 N1 1.335(11) . ?
C017 H017 0.9500 . ?
C018 N1 1.320(12) . ?
C018 H018 0.9500 . ?
N2 O3 1.230(10) . ?
N2 O4 1.233(10) . ?

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
H5A O5 H5C 117(10) . . ?
O2 C003 O1 122.6(7) . . ?
O2 C003 C004 126.9(7) . . ?
O1 C003 C004 110.3(6) . . ?
C011 C004 C005 120.9(7) . . ?
C011 C004 C003 117.6(6) . . ?
C005 C004 C003 121.4(7) . . ?
C007 C005 C004 119.4(7) . . ?
C007 C005 H005 120.3 . . ?
C004 C005 H005 120.3 . . ?
C007 C006 C014 123.3(7) . . ?
C007 C006 N2 118.6(7) . . ?
C014 C006 N2 118.0(7) . . ?
C006 C007 C005 119.3(7) . . ?
C006 C007 H007 120.3 . . ?
C005 C007 H007 120.3 . . ?
C010 C008 C018 117.3(8) . . ?
C010 C008 H008 121.3 . . ?
C018 C008 H008 121.3 . . ?
C008 C010 O1 124.5(7) . . ?
C008 C010 C012 119.4(7) . . ?
O1 C010 C012 116.0(6) . . ?
C014 C011 C004 119.7(7) . . ?
C014 C011 H011 120.2 . . ?
C004 C011 H011 120.2 . . ?
C017 C012 C010 117.6(7) . . ?
C017 C012 H012 121.2 . . ?
C010 C012 H012 121.2 . . ?
C011 C014 C006 117.4(8) . . ?
C011 C014 H014 121.3 . . ?
C006 C014 H014 121.3 . . ?
N1 C017 C012 124.3(8) . . ?
N1 C017 H017 117.8 . . ?
C012 C017 H017 117.8 . . ?
N1 C018 C008 124.9(7) . . ?
N1 C018 H018 117.6 . . ?
C008 C018 H018 117.6 . . ?
C018 N1 C017 116.4(8) . . ?
O3 N2 O4 123.9(7) . . ?
O3 N2 C006 117.2(7) . . ?
O4 N2 C006 118.8(7) . . ?
C003 O1 C010 120.4(6) . . ?

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
O2 C003 C004 C011 -8.2(12) . . . . ?
O1 C003 C004 C011 174.7(7) . . . . ?
O2 C003 C004 C005 169.1(9) . . . . ?
O1 C003 C004 C005 -8.1(11) . . . . ?
C011 C004 C005 C007 1.1(13) . . . . ?
C003 C004 C005 C007 -176.0(8) . . . . ?
C014 C006 C007 C005 1.6(14) . . . . ?
N2 C006 C007 C005 -179.7(8) . . . . ?
C004 C005 C007 C006 -2.1(13) . . . . ?
C018 C008 C010 O1 174.4(8) . . . . ?
C018 C008 C010 C012 -2.6(13) . . . . ?
C005 C004 C011 C014 0.6(13) . . . . ?
C003 C004 C011 C014 177.8(7) . . . . ?
C008 C010 C012 C017 2.7(14) . . . . ?
O1 C010 C012 C017 -174.6(8) . . . . ?
C004 C011 C014 C006 -1.2(12) . . . . ?
C007 C006 C014 C011 0.1(13) . . . . ?
N2 C006 C014 C011 -178.6(8) . . . . ?
C010 C012 C017 N1 -2.3(16) . . . . ?
C010 C008 C018 N1 2.1(15) . . . . ?
C008 C018 N1 C017 -1.7(15) . . . . ?
C012 C017 N1 C018 1.7(16) . . . . ?
C007 C006 N2 O3 12.9(12) . . . . ?
C014 C006 N2 O3 -168.3(8) . . . . ?
C007 C006 N2 O4 -168.5(9) . . . . ?
C014 C006 N2 O4 10.3(12) . . . . ?
O2 C003 O1 C010 -1.6(12) . . . . ?
C004 C003 O1 C010 175.7(7) . . . . ?
C008 C010 O1 C003 53.9(12) . . . . ?
C012 C010 O1 C003 -129.0(8) . . . . ?

_refine_diff_density_max         0.372
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.100

_shelxl_version_number           2014-3





# start Validation Reply Form
_vrf_PLAT340_3                   
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01218 Ang.  
RESPONSE: The above alert is generated due to poor quality of the crystal.
;
_vrf_PLAT417_3                   
;
PROBLEM: Short Inter D-H..H-D       H5C    ..  H5C     ..       1.96 Ang.  
RESPONSE: The close proximity occurs due to the presence of strong O-H...O hydrogen bond between water molecules
;
# end Validation Reply Form

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1544054'
_audit_update_record             
;
2017-04-14 deposited with the CCDC.
2017-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 N O5'
_chemical_formula_weight         259.21

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.228(2)
_cell_length_b                   7.888(3)
_cell_length_c                   20.958(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1195.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2209
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      33.3

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.722

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            11284
_diffrn_reflns_av_unetI/netI     0.0857
_diffrn_reflns_av_R_equivalents  0.1234
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.943
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2338
_reflns_number_gt                1695
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXL-14 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-14 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0450P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 486 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2338
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.1333
_refine_ls_wR_factor_gt          0.1149
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.003
_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
C002 C -0.0060(7) 0.6948(6) 0.0835(2) 0.0265(10) Uani 1 1 d . . . . .
C004 C -0.1038(7) 0.7082(6) 0.0266(2) 0.0308(11) Uani 1 1 d . . . . .
H004 H -0.1736 0.8074 0.0176 0.037 Uiso 1 1 calc R U . . .
C005 C 0.0917(7) 0.5488(6) 0.0979(2) 0.0298(11) Uani 1 1 d . . . . .
H005 H 0.1547 0.5396 0.1375 0.036 Uiso 1 1 calc R U . . .
C006 C 0.1558(6) 0.1683(6) -0.1378(2) 0.0291(11) Uani 1 1 d . . . . .
C007 C 0.1406(7) 0.3164(6) -0.0943(2) 0.0304(11) Uani 1 1 d . . . . .
C008 C 0.1062(7) -0.1249(6) -0.1635(2) 0.0318(12) Uani 1 1 d . . . . .
H008 H 0.0594 -0.2341 -0.1531 0.038 Uiso 1 1 calc R U . . .
C009 C 0.2696(7) 0.0584(6) -0.2382(2) 0.0346(12) Uani 1 1 d . . . . .
H009 H 0.3299 0.0739 -0.2780 0.042 Uiso 1 1 calc R U . . .
C010 C 0.1992(7) -0.0984(6) -0.2204(2) 0.0308(12) Uani 1 1 d . . . . .
C011 C 0.0038(7) 0.4337(5) -0.0026(2) 0.0286(11) Uani 1 1 d . . . . .
C014 C -0.0987(7) 0.5755(6) -0.0171(2) 0.0301(11) Uani 1 1 d . . . . .
H014 H -0.1647 0.5827 -0.0562 0.036 Uiso 1 1 calc R U . . .
C015 C 0.2486(7) 0.1912(6) -0.1957(2) 0.0341(12) Uani 1 1 d . . . . .
H015 H 0.2980 0.2994 -0.2060 0.041 Uiso 1 1 calc R U . . .
C016 C 0.0823(7) 0.0104(6) -0.1217(2) 0.0293(11) Uani 1 1 d . . . . .
H016 H 0.0168 -0.0046 -0.0828 0.035 Uiso 1 1 calc R U . . .
C017 C 0.0981(7) 0.4157(6) 0.0545(2) 0.0305(11) Uani 1 1 d . . . . .
H017 H 0.1653 0.3152 0.0638 0.037 Uiso 1 1 calc R U . . .
N1 N 0.2264(6) -0.2404(6) -0.2651(2) 0.0418(11) Uani 1 1 d . . . . .
O1 O 0.0145(5) 0.2960(4) -0.04741(14) 0.0320(8) Uani 1 1 d . . . . .
O2 O -0.0008(5) 0.8222(4) 0.12846(14) 0.0371(9) Uani 1 1 d . . . . .
H2 H -0.0629 0.9054 0.1155 0.056 Uiso 1 1 calc R U . . .
O3 O 0.2332(6) 0.4436(4) -0.09955(18) 0.0542(12) Uani 1 1 d . . . . .
O4 O 0.1955(6) -0.3851(5) -0.24518(18) 0.0514(11) Uani 1 1 d . . . . .
O5 O 0.2760(7) -0.2081(5) -0.3201(2) 0.0684(13) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C002 O2 1.378(5) . ?
C002 C005 1.384(6) . ?
C002 C004 1.391(6) . ?
C004 C014 1.392(7) . ?
C004 H004 0.9500 . ?
C005 C017 1.389(6) . ?
C005 H005 0.9500 . ?
C006 C016 1.396(6) . ?
C006 C015 1.399(6) . ?
C006 C007 1.486(6) . ?
C007 O3 1.211(5) . ?
C007 O1 1.349(5) . ?
C008 C010 1.385(7) . ?
C008 C016 1.391(6) . ?
C008 H008 0.9500 . ?
C009 C015 1.383(6) . ?
C009 C010 1.389(6) . ?
C009 H009 0.9500 . ?
C010 N1 1.475(6) . ?
C011 C014 1.375(6) . ?
C011 C017 1.386(6) . ?
C011 O1 1.437(5) . ?
C014 H014 0.9500 . ?
C015 H015 0.9500 . ?
C016 H016 0.9500 . ?
C017 H017 0.9500 . ?
N1 O5 1.233(6) . ?
N1 O4 1.236(6) . ?
O2 H2 0.8400 . ?

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
O2 C002 C005 116.4(4) . . ?
O2 C002 C004 123.0(4) . . ?
C005 C002 C004 120.6(4) . . ?
C002 C004 C014 119.6(4) . . ?
C002 C004 H004 120.2 . . ?
C014 C004 H004 120.2 . . ?
C002 C005 C017 120.2(4) . . ?
C002 C005 H005 119.9 . . ?
C017 C005 H005 119.9 . . ?
C016 C006 C015 120.5(4) . . ?
C016 C006 C007 121.7(4) . . ?
C015 C006 C007 117.8(4) . . ?
O3 C007 O1 122.6(4) . . ?
O3 C007 C006 123.6(4) . . ?
O1 C007 C006 113.8(4) . . ?
C010 C008 C016 119.1(4) . . ?
C010 C008 H008 120.5 . . ?
C016 C008 H008 120.5 . . ?
C015 C009 C010 117.4(4) . . ?
C015 C009 H009 121.3 . . ?
C010 C009 H009 121.3 . . ?
C008 C010 C009 123.0(4) . . ?
C008 C010 N1 119.8(4) . . ?
C009 C010 N1 117.2(4) . . ?
C014 C011 C017 122.6(4) . . ?
C014 C011 O1 120.0(4) . . ?
C017 C011 O1 117.4(4) . . ?
C011 C014 C004 118.7(4) . . ?
C011 C014 H014 120.6 . . ?
C004 C014 H014 120.6 . . ?
C009 C015 C006 120.9(4) . . ?
C009 C015 H015 119.5 . . ?
C006 C015 H015 119.5 . . ?
C008 C016 C006 119.1(4) . . ?
C008 C016 H016 120.5 . . ?
C006 C016 H016 120.5 . . ?
C011 C017 C005 118.1(4) . . ?
C011 C017 H017 120.9 . . ?
C005 C017 H017 120.9 . . ?
O5 N1 O4 124.0(5) . . ?
O5 N1 C010 118.4(5) . . ?
O4 N1 C010 117.5(5) . . ?
C007 O1 C011 114.9(3) . . ?
C002 O2 H2 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C002 C004 C014 178.4(5) . . . . ?
C005 C002 C004 C014 -1.9(7) . . . . ?
O2 C002 C005 C017 -178.3(4) . . . . ?
C004 C002 C005 C017 2.0(7) . . . . ?
C016 C006 C007 O3 164.0(5) . . . . ?
C015 C006 C007 O3 -15.3(8) . . . . ?
C016 C006 C007 O1 -15.4(7) . . . . ?
C015 C006 C007 O1 165.3(4) . . . . ?
C016 C008 C010 C009 -0.4(7) . . . . ?
C016 C008 C010 N1 179.8(4) . . . . ?
C015 C009 C010 C008 1.7(7) . . . . ?
C015 C009 C010 N1 -178.4(5) . . . . ?
C017 C011 C014 C004 1.8(7) . . . . ?
O1 C011 C014 C004 -178.8(4) . . . . ?
C002 C004 C014 C011 0.0(7) . . . . ?
C010 C009 C015 C006 -1.5(8) . . . . ?
C016 C006 C015 C009 0.0(8) . . . . ?
C007 C006 C015 C009 179.3(5) . . . . ?
C010 C008 C016 C006 -1.2(7) . . . . ?
C015 C006 C016 C008 1.4(7) . . . . ?
C007 C006 C016 C008 -177.9(5) . . . . ?
C014 C011 C017 C005 -1.7(7) . . . . ?
O1 C011 C017 C005 178.9(4) . . . . ?
C002 C005 C017 C011 -0.3(7) . . . . ?
C008 C010 N1 O5 166.0(5) . . . . ?
C009 C010 N1 O5 -13.9(7) . . . . ?
C008 C010 N1 O4 -13.2(7) . . . . ?
C009 C010 N1 O4 167.0(5) . . . . ?
O3 C007 O1 C011 -2.5(7) . . . . ?
C006 C007 O1 C011 176.9(4) . . . . ?
C014 C011 O1 C007 82.3(6) . . . . ?
C017 C011 O1 C007 -98.2(5) . . . . ?

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.047

_shelxl_version_number           2014-3



