# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_USA
_database_code_depnum_ccdc_archive 'CCDC 1495375'
_audit_update_record             
;
2016-07-22 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT213_USA                 
;
PROBLEM: Atom N3              has ADP max/min Ratio .....        5.1 prolat
RESPONSE: Poor quality, weakly diffracting crystal
;
_vrf_THETM01_USA                 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: Weak diffraction
;
# Added during the CSD deposition process: Friday 22 July 2016 10:00 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 N2 O4'
_chemical_formula_weight         196.16

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      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                   4.7242(12)
_cell_length_b                   12.369(3)
_cell_length_c                   13.831(3)
_cell_angle_alpha                90
_cell_angle_beta                 82.466(8)
_cell_angle_gamma                90
_cell_volume                     801.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6579
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      23.3

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.099
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.043
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5421
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6579
_diffrn_reflns_av_unetI/netI     0.1436
_diffrn_reflns_av_R_equivalents  0.1669
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.217
_diffrn_reflns_theta_max         23.309
_diffrn_reflns_theta_full        23.309
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1154
_reflns_number_gt                719
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0446P)²+3.6472P] 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_number_reflns         1154
_refine_ls_number_parameters     127
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.1789
_refine_ls_R_factor_gt           0.1138
_refine_ls_wR_factor_ref         0.1931
_refine_ls_wR_factor_gt          0.1711
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.140
_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 1.5028(10) 0.6393(3) 0.0219(3) 0.0128(13) Uani 1 1 d . . . . .
N1 N 1.0708(12) 0.7076(5) 0.0817(4) 0.0160(16) Uani 1 1 d . . . . .
H1A H 1.1136 0.7713 0.0556 0.019 Uiso 1 1 calc R U . . .
H1B H 0.9024 0.6967 0.1158 0.019 Uiso 1 1 calc R U . . .
O2 O 0.2709(10) 0.4046(4) 0.3837(3) 0.0190(14) Uani 1 1 d . . . . .
H2 H 0.2207 0.4545 0.4235 0.023 Uiso 1 1 calc R U . . .
C2 C 1.2612(16) 0.6274(6) 0.0697(5) 0.0100(18) Uani 1 1 d . U . . .
O3 O 0.2872(10) 0.5987(4) 0.4609(3) 0.0167(13) Uani 1 1 d . . . . .
N3 N 1.1905(12) 0.5297(4) 0.1119(4) 0.0117(15) Uani 1 1 d . U . . .
H3 H 1.3068 0.4761 0.0926 0.014 Uiso 1 1 calc R U . . .
O4 O 0.6529(10) 0.7074(4) 0.4061(3) 0.0186(14) Uani 1 1 d . . . . .
H4 H 0.5761 0.7469 0.4516 0.022 Uiso 1 1 calc R U . . .
C4 C 0.9568(15) 0.5026(6) 0.1821(5) 0.0130(18) Uani 1 1 d . . . . .
C5 C 0.8359(16) 0.3979(6) 0.1793(5) 0.0153(19) Uani 1 1 d . . . . .
H5 H 0.9092 0.3483 0.1298 0.018 Uiso 1 1 calc R U . . .
C6 C 0.6120(16) 0.3677(6) 0.2484(5) 0.0145(18) Uani 1 1 d . U . . .
H6 H 0.5353 0.2968 0.2469 0.017 Uiso 1 1 calc R U . . .
C7 C 0.4997(15) 0.4386(5) 0.3188(5) 0.0091(17) Uani 1 1 d . U . . .
C8 C 0.6179(15) 0.5412(6) 0.3263(5) 0.0107(18) Uani 1 1 d . . . . .
C9 C 0.8525(16) 0.5714(6) 0.2575(5) 0.0142(19) Uani 1 1 d . . . . .
H9 H 0.9400 0.6399 0.2630 0.017 Uiso 1 1 calc R U . . .
C10 C 0.5039(16) 0.6172(6) 0.4033(5) 0.0112(18) Uani 1 1 d . 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 1.250(8) . ?
N1 C2 1.335(8) . ?
O2 C7 1.377(8) . ?
C2 N3 1.363(8) . ?
O3 C10 1.233(8) . ?
N3 C4 1.412(9) . ?
O4 C10 1.323(8) . ?
C4 C9 1.386(10) . ?
C4 C5 1.418(10) . ?
C5 C6 1.381(10) . ?
C6 C7 1.365(9) . ?
C7 C8 1.396(9) . ?
C8 C9 1.413(10) . ?
C8 C10 1.469(9) . ?

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
O1 C2 N1 122.1(6) . . ?
O1 C2 N3 119.1(6) . . ?
N1 C2 N3 118.8(6) . . ?
C2 N3 C4 129.1(6) . . ?
C9 C4 N3 122.7(6) . . ?
C9 C4 C5 118.5(7) . . ?
N3 C4 C5 118.7(7) . . ?
C6 C5 C4 120.2(7) . . ?
C7 C6 C5 120.7(7) . . ?
C6 C7 O2 117.9(6) . . ?
C6 C7 C8 121.0(7) . . ?
O2 C7 C8 121.1(6) . . ?
C7 C8 C9 118.4(6) . . ?
C7 C8 C10 121.6(6) . . ?
C9 C8 C10 120.0(6) . . ?
C4 C9 C8 121.0(7) . . ?
O3 C10 O4 122.5(6) . . ?
O3 C10 C8 123.0(7) . . ?
O4 C10 C8 114.5(6) . . ?

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 H1A O3 0.88 2.17 3.022(7) 164.1 4_675
N1 H1B O1 0.88 2.53 3.030(8) 116.9 1_455
O2 H2 O3 0.84 1.90 2.633(7) 145.8 .
N3 H3 O1 0.88 2.23 3.032(7) 151.0 3_865
O4 H4 O1 0.84 1.72 2.523(6) 159.1 4_476
C6 H6 O4 0.95 2.64 3.281(9) 124.9 2_645
N1 H1A O3 0.88 2.17 3.022(7) 164.1 4_675
N1 H1B O1 0.88 2.53 3.030(8) 116.9 1_455
O2 H2 O3 0.84 1.90 2.633(7) 145.8 .
N3 H3 O1 0.88 2.23 3.032(7) 151.0 3_865
O4 H4 O1 0.84 1.72 2.523(6) 159.1 4_476
C6 H6 O4 0.95 2.64 3.281(9) 124.9 2_645

_refine_diff_density_max         0.422
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.096



####################################################################### 
# 
# 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_THF
_database_code_depnum_ccdc_archive 'CCDC 1495376'
_audit_update_record             
;
2016-07-22 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H16 N2 O5'
_chemical_formula_weight         268.27

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   22.3090(19)
_cell_length_b                   19.1478(16)
_cell_length_c                   9.0100(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.398(3)
_cell_angle_gamma                90.00
_cell_volume                     3847.6(6)
_cell_formula_units_Z            12
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    429
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      21.39

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1704
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9676
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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  'Bruker D8 Venture'
_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            43079
_diffrn_reflns_av_R_equivalents  0.0930
_diffrn_reflns_av_sigmaI/netI    0.0672
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         24.84
_reflns_number_total             6619
_reflns_number_gt                4236
_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)+(0.0634P)²+6.3091P] 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         6619
_refine_ls_number_parameters     514
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.1622
_refine_ls_wR_factor_gt          0.1375
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_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
O1 O 0.33151(11) 0.38763(12) 0.7376(3) 0.0310(6) Uani 1 1 d . . .
N1 N 0.41100(13) 0.33991(15) 0.6252(3) 0.0304(8) Uani 1 1 d . . .
H1A H 0.4248 0.3811 0.5996 0.037 Uiso 1 1 calc R . .
H1B H 0.4305 0.3018 0.6009 0.037 Uiso 1 1 calc R . .
O2 O 0.15661(12) 0.16511(13) 1.0690(3) 0.0412(7) Uani 1 1 d . . .
H2O H 0.1324 0.1963 1.0944 0.049 Uiso 1 1 calc R . .
C2 C 0.36031(15) 0.33514(18) 0.7012(4) 0.0231(8) Uani 1 1 d . . .
O3 O 0.11675(11) 0.29190(13) 1.0930(3) 0.0363(7) Uani 1 1 d . . .
N3 N 0.34345(12) 0.26985(14) 0.7376(3) 0.0265(7) Uani 1 1 d . . .
H3 H 0.3663 0.2361 0.7043 0.032 Uiso 1 1 calc R . .
O4 O 0.16396(10) 0.37827(12) 0.9776(3) 0.0304(6) Uani 1 1 d . . .
H4O H 0.1364 0.4020 1.0146 0.037 Uiso 1 1 calc R . .
C4 C 0.29396(15) 0.24793(17) 0.8221(4) 0.0226(8) Uani 1 1 d . . .
O5 O 0.09682(10) 0.46936(12) 1.0819(3) 0.0276(6) Uani 1 1 d . . .
C5 C 0.29127(16) 0.17700(18) 0.8562(4) 0.0301(9) Uani 1 1 d . . .
H5 H 0.3218 0.1466 0.8227 0.036 Uiso 1 1 calc R . .
O6 O 0.04491(12) 0.80246(13) 1.1263(3) 0.0469(8) Uani 1 1 d . . .
H6O H 0.0728 0.8126 1.0691 0.056 Uiso 1 1 calc R . .
C6 C 0.24540(17) 0.15041(18) 0.9370(4) 0.0330(9) Uani 1 1 d . . .
H6 H 0.2441 0.1018 0.9580 0.040 Uiso 1 1 calc R . .
O7 O 0.13609(11) 0.77621(12) 0.9591(3) 0.0310(6) Uani 1 1 d . . .
C7 C 0.20067(16) 0.19414(19) 0.9884(4) 0.0286(9) Uani 1 1 d . . .
O8 O 0.15989(10) 0.66486(11) 0.9137(3) 0.0258(6) Uani 1 1 d . . .
H8O H 0.1882 0.6839 0.8692 0.031 Uiso 1 1 calc R . .
C8 C 0.20305(15) 0.26508(17) 0.9566(4) 0.0226(8) Uani 1 1 d . . .
O9 O 0.24975(10) 0.70219(12) 0.7674(2) 0.0233(5) Uani 1 1 d . . .
C9 C 0.25001(15) 0.29165(17) 0.8721(4) 0.0231(8) Uani 1 1 d . . .
H9 H 0.2514 0.3401 0.8494 0.028 Uiso 1 1 calc R . .
O10 O 0.46652(10) 0.58914(13) 0.3642(3) 0.0317(6) Uani 1 1 d . . .
H10O H 0.4650 0.5490 0.4014 0.038 Uiso 1 1 calc R . .
C10 C 0.15753(16) 0.31282(18) 1.0139(4) 0.0266(8) Uani 1 1 d . . .
O11 O 0.42468(10) 0.49081(12) 0.5319(3) 0.0278(6) Uani 1 1 d . . .
N11 N 0.03283(12) 0.39890(15) 1.2015(3) 0.0262(7) Uani 1 1 d . . .
H11A H 0.0558 0.3622 1.1875 0.031 Uiso 1 1 calc R . .
H11B H -0.0009 0.3945 1.2492 0.031 Uiso 1 1 calc R . .
O12 O 0.34324(10) 0.51272(12) 0.6624(3) 0.0309(6) Uani 1 1 d . . .
H12O H 0.3477 0.4705 0.6852 0.037 Uiso 1 1 calc R . .
C12 C 0.04930(14) 0.46156(17) 1.1499(4) 0.0204(8) Uani 1 1 d . . .
O13 O 0.44933(12) 0.18949(14) 0.6551(3) 0.0386(7) Uani 1 1 d . . .
N13 N 0.01274(12) 0.51572(14) 1.1805(3) 0.0227(7) Uani 1 1 d . . .
H13 H -0.0219 0.5048 1.2188 0.027 Uiso 1 1 calc R . .
O14 O -0.08715(10) 0.47071(13) 1.3434(3) 0.0303(6) Uani 1 1 d . . .
C14 C 0.02332(14) 0.58745(17) 1.1588(4) 0.0205(7) Uani 1 1 d . . .
O15 O 0.29052(13) 0.91610(13) 0.5369(3) 0.0447(7) Uani 1 1 d . . .
C15 C -0.01557(16) 0.6341(2) 1.2264(4) 0.0326(9) Uani 1 1 d . . .
H15 H -0.0478 0.6165 1.2825 0.039 Uiso 1 1 calc R . .
C16 C -0.00809(17) 0.7050(2) 1.2131(5) 0.0387(10) Uani 1 1 d . . .
H16 H -0.0352 0.7358 1.2598 0.046 Uiso 1 1 calc R . .
C17 C 0.03853(16) 0.73207(18) 1.1324(4) 0.0305(9) Uani 1 1 d . . .
C18 C 0.07722(15) 0.68602(18) 1.0623(4) 0.0230(8) Uani 1 1 d . . .
C19 C 0.06919(14) 0.61380(17) 1.0761(4) 0.0198(7) Uani 1 1 d . . .
H19 H 0.0956 0.5827 1.0279 0.024 Uiso 1 1 calc R . .
C20 C 0.12656(15) 0.71322(18) 0.9743(4) 0.0234(8) Uani 1 1 d . . .
N21 N 0.22257(13) 0.81474(15) 0.7343(3) 0.0293(7) Uani 1 1 d . . .
H21A H 0.1969 0.8129 0.8069 0.035 Uiso 1 1 calc R . .
H21B H 0.2271 0.8538 0.6843 0.035 Uiso 1 1 calc R . .
C22 C 0.25457(14) 0.75838(18) 0.7001(4) 0.0212(8) Uani 1 1 d . . .
N23 N 0.29327(12) 0.76657(14) 0.5875(3) 0.0233(7) Uani 1 1 d . . .
H23 H 0.2919 0.8071 0.5414 0.028 Uiso 1 1 calc R . .
C24 C 0.33526(14) 0.71821(17) 0.5357(4) 0.0196(7) Uani 1 1 d . . .
C25 C 0.37547(14) 0.74179(18) 0.4311(4) 0.0237(8) Uani 1 1 d . . .
H25 H 0.3731 0.7888 0.3976 0.028 Uiso 1 1 calc R . .
C26 C 0.41863(14) 0.69839(19) 0.3754(4) 0.0264(8) Uani 1 1 d . . .
H26 H 0.4455 0.7156 0.3038 0.032 Uiso 1 1 calc R . .
C27 C 0.42322(14) 0.62979(18) 0.4227(4) 0.0227(8) Uani 1 1 d . . .
C28 C 0.38256(14) 0.60452(17) 0.5265(4) 0.0200(7) Uani 1 1 d . . .
C29 C 0.33895(14) 0.64943(17) 0.5824(4) 0.0198(7) Uani 1 1 d . . .
H29 H 0.3116 0.6325 0.6531 0.024 Uiso 1 1 calc R . .
C30 C 0.38535(14) 0.53145(18) 0.5744(4) 0.0230(8) Uani 1 1 d . . .
C31 C 0.4548(3) 0.1659(2) 0.5055(5) 0.0609(14) Uani 1 1 d . . .
H31A H 0.4837 0.1955 0.4524 0.073 Uiso 1 1 calc R . .
H31B H 0.4154 0.1685 0.4523 0.073 Uiso 1 1 calc R . .
C32 C 0.4758(3) 0.0939(3) 0.5118(5) 0.0640(15) Uani 1 1 d . . .
H32A H 0.5031 0.0841 0.4293 0.077 Uiso 1 1 calc R . .
H32B H 0.4416 0.0610 0.5054 0.077 Uiso 1 1 calc R . .
C33 C 0.5076(2) 0.0875(2) 0.6554(5) 0.0555(13) Uani 1 1 d . . .
H33A H 0.5511 0.0960 0.6445 0.067 Uiso 1 1 calc R . .
H33B H 0.5019 0.0403 0.6978 0.067 Uiso 1 1 calc R . .
C34 C 0.48067(19) 0.1417(2) 0.7517(4) 0.0392(10) Uani 1 1 d . . .
H34A H 0.4526 0.1200 0.8216 0.047 Uiso 1 1 calc R . .
H34B H 0.5124 0.1664 0.8099 0.047 Uiso 1 1 calc R . .
C35 C -0.14891(15) 0.48129(19) 1.3018(4) 0.0296(9) Uani 1 1 d . . .
H35A H -0.1592 0.4564 1.2083 0.036 Uiso 1 1 calc R . .
H35B H -0.1577 0.5316 1.2884 0.036 Uiso 1 1 calc R . .
C36 C -0.18294(16) 0.4518(2) 1.4287(4) 0.0332(9) Uani 1 1 d . . .
H36A H -0.1873 0.4005 1.4199 0.040 Uiso 1 1 calc R . .
H36B H -0.2232 0.4733 1.4346 0.040 Uiso 1 1 calc R . .
C37 C -0.14368(17) 0.4714(2) 1.5620(4) 0.0394(10) Uani 1 1 d . . .
H37A H -0.1569 0.5162 1.6054 0.047 Uiso 1 1 calc R . .
H37B H -0.1449 0.4347 1.6392 0.047 Uiso 1 1 calc R . .
C38 C -0.08173(17) 0.4780(2) 1.5018(4) 0.0357(10) Uani 1 1 d . . .
H38A H -0.0644 0.5241 1.5280 0.043 Uiso 1 1 calc R . .
H38B H -0.0553 0.4411 1.5439 0.043 Uiso 1 1 calc R . .
C39 C 0.25799(18) 0.9781(2) 0.4996(5) 0.0375(10) Uani 1 1 d . . .
H39A H 0.2150 0.9723 0.5210 0.045 Uiso 1 1 calc R . .
H39B H 0.2618 0.9892 0.3930 0.045 Uiso 1 1 calc R . .
C40 C 0.2851(2) 1.0355(2) 0.5943(6) 0.0663(15) Uani 1 1 d . . .
H40A H 0.3097 1.0672 0.5338 0.080 Uiso 1 1 calc R . .
H40B H 0.2534 1.0631 0.6421 0.080 Uiso 1 1 calc R . .
C41 C 0.3230(2) 0.9988(2) 0.7073(5) 0.0489(12) Uani 1 1 d . . .
H41A H 0.3582 1.0273 0.7380 0.059 Uiso 1 1 calc R . .
H41B H 0.2998 0.9866 0.7959 0.059 Uiso 1 1 calc R . .
C42 C 0.3411(2) 0.9356(2) 0.6249(7) 0.0688(16) Uani 1 1 d . . .
H42A H 0.3756 0.9460 0.5616 0.083 Uiso 1 1 calc R . .
H42B H 0.3525 0.8977 0.6947 0.083 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.241(4) . ?
N1 C2 1.340(4) . ?
O2 C7 1.356(4) . ?
C2 N3 1.348(4) . ?
O3 C10 1.236(4) . ?
N3 C4 1.420(4) . ?
O4 C10 1.304(4) . ?
C4 C9 1.373(5) . ?
C4 C5 1.394(5) . ?
O5 C12 1.246(4) . ?
C5 C6 1.369(5) . ?
O6 C17 1.357(4) . ?
C6 C7 1.391(5) . ?
O7 C20 1.233(4) . ?
C7 C8 1.390(5) . ?
O8 C20 1.315(4) . ?
C8 C9 1.405(5) . ?
C8 C10 1.469(5) . ?
O9 C22 1.241(4) . ?
O10 C27 1.357(4) . ?
O11 C30 1.240(4) . ?
N11 C12 1.341(4) . ?
O12 C30 1.295(4) . ?
C12 N13 1.352(4) . ?
O13 C31 1.430(5) . ?
O13 C34 1.433(4) . ?
N13 C14 1.408(4) . ?
O14 C38 1.436(4) . ?
O14 C35 1.434(4) . ?
C14 C19 1.376(4) . ?
C14 C15 1.395(5) . ?
O15 C42 1.413(5) . ?
O15 C39 1.428(4) . ?
C15 C16 1.374(5) . ?
C16 C17 1.384(5) . ?
C17 C18 1.396(5) . ?
C18 C19 1.400(5) . ?
C18 C20 1.468(5) . ?
N21 C22 1.334(4) . ?
C22 N23 1.357(4) . ?
N23 C24 1.405(4) . ?
C24 C29 1.385(5) . ?
C24 C25 1.392(4) . ?
C25 C26 1.376(5) . ?
C26 C27 1.384(5) . ?
C27 C28 1.405(5) . ?
C28 C29 1.401(4) . ?
C28 C30 1.465(5) . ?
C31 C32 1.457(6) . ?
C32 C33 1.465(6) . ?
C33 C34 1.490(6) . ?
C35 C36 1.498(5) . ?
C36 C37 1.516(5) . ?
C37 C38 1.502(5) . ?
C39 C40 1.508(6) . ?
C40 C41 1.484(6) . ?
C41 C42 1.480(6) . ?

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
O1 C2 N1 121.9(3) . . ?
O1 C2 N3 122.5(3) . . ?
N1 C2 N3 115.6(3) . . ?
C2 N3 C4 129.0(3) . . ?
C9 C4 C5 119.2(3) . . ?
C9 C4 N3 124.5(3) . . ?
C5 C4 N3 116.4(3) . . ?
C6 C5 C4 121.1(3) . . ?
C5 C6 C7 120.3(3) . . ?
O2 C7 C8 122.9(3) . . ?
O2 C7 C6 117.8(3) . . ?
C8 C7 C6 119.3(3) . . ?
C7 C8 C9 119.9(3) . . ?
C7 C8 C10 120.4(3) . . ?
C9 C8 C10 119.7(3) . . ?
C4 C9 C8 120.3(3) . . ?
O3 C10 O4 122.9(3) . . ?
O3 C10 C8 121.7(3) . . ?
O4 C10 C8 115.4(3) . . ?
O5 C12 N11 121.4(3) . . ?
O5 C12 N13 122.2(3) . . ?
N11 C12 N13 116.3(3) . . ?
C31 O13 C34 108.7(3) . . ?
C12 N13 C14 128.0(3) . . ?
C38 O14 C35 107.7(3) . . ?
C19 C14 C15 118.7(3) . . ?
C19 C14 N13 124.2(3) . . ?
C15 C14 N13 117.1(3) . . ?
C42 O15 C39 107.8(3) . . ?
C16 C15 C14 121.1(3) . . ?
C15 C16 C17 120.7(3) . . ?
O6 C17 C16 118.3(3) . . ?
O6 C17 C18 122.9(3) . . ?
C16 C17 C18 118.8(3) . . ?
C17 C18 C19 120.1(3) . . ?
C17 C18 C20 120.0(3) . . ?
C19 C18 C20 119.8(3) . . ?
C14 C19 C18 120.6(3) . . ?
O7 C20 O8 122.8(3) . . ?
O7 C20 C18 122.7(3) . . ?
O8 C20 C18 114.4(3) . . ?
O9 C22 N21 122.3(3) . . ?
O9 C22 N23 122.0(3) . . ?
N21 C22 N23 115.7(3) . . ?
C22 N23 C24 127.9(3) . . ?
C29 C24 C25 118.7(3) . . ?
C29 C24 N23 124.1(3) . . ?
C25 C24 N23 117.2(3) . . ?
C26 C25 C24 121.3(3) . . ?
C25 C26 C27 120.5(3) . . ?
O10 C27 C26 118.2(3) . . ?
O10 C27 C28 122.6(3) . . ?
C26 C27 C28 119.2(3) . . ?
C29 C28 C27 119.6(3) . . ?
C29 C28 C30 120.3(3) . . ?
C27 C28 C30 120.1(3) . . ?
C24 C29 C28 120.7(3) . . ?
O11 C30 O12 123.0(3) . . ?
O11 C30 C28 122.3(3) . . ?
O12 C30 C28 114.7(3) . . ?
O13 C31 C32 107.2(4) . . ?
C31 C32 C33 105.2(4) . . ?
C32 C33 C34 105.2(4) . . ?
O13 C34 C33 106.8(3) . . ?
O14 C35 C36 104.4(3) . . ?
C35 C36 C37 102.6(3) . . ?
C38 C37 C36 104.7(3) . . ?
O14 C38 C37 107.2(3) . . ?
O15 C39 C40 106.2(3) . . ?
C41 C40 C39 104.9(4) . . ?
C42 C41 C40 101.6(4) . . ?
O15 C42 C41 105.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        24.84
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.063
####################################################################### 
# 
# 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_A019A23
_database_code_depnum_ccdc_archive 'CCDC 1495377'
_audit_update_record             
;
2016-07-22 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H8 N2 O4, C2 H3 N'
_chemical_formula_sum            'C10 H11 N3 O4'
_chemical_formula_weight         237.22

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   13.3689(18)
_cell_length_b                   15.143(2)
_cell_length_c                   18.786(3)
_cell_angle_alpha                77.079(3)
_cell_angle_beta                 74.563(4)
_cell_angle_gamma                63.839(3)
_cell_volume                     3265.4(8)
_cell_formula_units_Z            12
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1215
_cell_measurement_theta_min      1.76
_cell_measurement_theta_max      30.17

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1488
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9578
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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  'Bruker D8 Venture'
_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            26914
_diffrn_reflns_av_R_equivalents  0.1028
_diffrn_reflns_av_sigmaI/netI    0.1162
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         23.34
_reflns_number_total             9285
_reflns_number_gt                5891
_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)+(0.1116P)²+2.0885P] 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         9285
_refine_ls_number_parameters     925
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1328
_refine_ls_R_factor_gt           0.0892
_refine_ls_wR_factor_ref         0.2243
_refine_ls_wR_factor_gt          0.2027
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
O1 O 0.3606(3) 1.5329(3) 0.13777(17) 0.0374(9) Uani 1 1 d . . .
N1 N 0.3108(3) 1.6623(3) 0.2001(2) 0.0352(11) Uani 1 1 d . . .
H1A H 0.3287 1.6230 0.2412 0.042 Uiso 1 1 calc R . .
H1B H 0.2845 1.7269 0.1991 0.042 Uiso 1 1 calc R . .
O2 O 0.2957(3) 1.6509(3) -0.20868(18) 0.0422(9) Uani 1 1 d . . .
H2O H 0.3235 1.5913 -0.2162 0.051 Uiso 1 1 calc R . .
C2 C 0.3238(4) 1.6236(4) 0.1389(3) 0.0316(12) Uani 1 1 d . . .
O3 O 0.3956(3) 1.4585(2) -0.17547(18) 0.0387(9) Uani 1 1 d . . .
N3 N 0.2960(3) 1.6909(3) 0.0781(2) 0.0320(10) Uani 1 1 d . . .
H3 H 0.2710 1.7534 0.0847 0.038 Uiso 1 1 calc R . .
O4 O 0.4324(3) 1.3985(2) -0.06081(17) 0.0369(9) Uani 1 1 d . . .
H4O H 0.4571 1.3444 -0.0779 0.044 Uiso 1 1 calc R . .
C4 C 0.3022(4) 1.6736(4) 0.0063(3) 0.0301(12) Uani 1 1 d . . .
O5 O 0.5207(3) 1.2204(2) -0.08501(18) 0.0383(9) Uani 1 1 d . . .
C5 C 0.2593(4) 1.7572(4) -0.0446(3) 0.0359(13) Uani 1 1 d . . .
H5 H 0.2288 1.8212 -0.0293 0.043 Uiso 1 1 calc R . .
O6 O 0.7511(3) 0.7577(2) 0.05867(18) 0.0421(9) Uani 1 1 d . . .
H6O H 0.7415 0.7734 0.1009 0.050 Uiso 1 1 calc R . .
C6 C 0.2603(4) 1.7487(4) -0.1158(3) 0.0382(13) Uani 1 1 d . . .
H6 H 0.2321 1.8067 -0.1496 0.046 Uiso 1 1 calc R . .
O7 O 0.6852(3) 0.8789(2) 0.15698(18) 0.0372(9) Uani 1 1 d . . .
C7 C 0.3023(4) 1.6557(4) -0.1389(3) 0.0351(13) Uani 1 1 d . . .
O8 O 0.6162(3) 1.0418(2) 0.12054(18) 0.0438(10) Uani 1 1 d . . .
H8O H 0.6150 1.0439 0.1651 0.053 Uiso 1 1 calc R . .
C8 C 0.3487(4) 1.5709(4) -0.0891(3) 0.0305(12) Uani 1 1 d . . .
O9 O 0.5994(3) 1.0839(2) 0.24642(17) 0.0372(9) Uani 1 1 d . . .
C9 C 0.3489(4) 1.5817(4) -0.0171(3) 0.0304(12) Uani 1 1 d . . .
H9 H 0.3819 1.5244 0.0161 0.036 Uiso 1 1 calc R . .
O10 O 0.3965(3) 1.4286(2) 0.46398(18) 0.0416(9) Uani 1 1 d . . .
H10O H 0.3761 1.4742 0.4292 0.050 Uiso 1 1 calc R . .
C10 C 0.3941(4) 1.4723(4) -0.1126(3) 0.0330(13) Uani 1 1 d . . .
O11 O 0.3747(3) 1.5035(3) 0.32633(18) 0.0371(9) Uani 1 1 d . . .
N11 N 0.4944(4) 1.2436(3) -0.2032(2) 0.0434(12) Uani 1 1 d . . .
H11A H 0.4599 1.3083 -0.2032 0.052 Uiso 1 1 calc R . .
H11B H 0.5037 1.2171 -0.2430 0.052 Uiso 1 1 calc R . .
C12 C 0.5329(4) 1.1848(4) -0.1422(3) 0.0345(13) Uani 1 1 d . . .
O13 O 0.8786(3) 1.0380(3) 0.39500(18) 0.0372(9) Uani 1 1 d . . .
N13 N 0.5836(3) 1.0867(3) -0.1466(2) 0.0333(10) Uani 1 1 d . . .
H13 H 0.5913 1.0694 -0.1901 0.040 Uiso 1 1 calc R . .
O14 O 0.7934(3) 1.1590(2) 0.72473(18) 0.0419(9) Uani 1 1 d . . .
H14O H 0.8159 1.0998 0.7446 0.050 Uiso 1 1 calc R . .
C14 C 0.6258(4) 1.0079(4) -0.0917(3) 0.0324(12) Uani 1 1 d . . .
O15 O 0.8734(3) 0.9675(2) 0.72703(19) 0.0414(9) Uani 1 1 d . . .
C15 C 0.6750(4) 0.9120(4) -0.1115(3) 0.0351(13) Uani 1 1 d . . .
H15 H 0.6796 0.9030 -0.1609 0.042 Uiso 1 1 calc R . .
O16 O 0.9079(3) 0.9059(2) 0.62149(18) 0.0389(9) Uani 1 1 d . . .
H16O H 0.9275 0.8522 0.6497 0.047 Uiso 1 1 calc R . .
C16 C 0.7167(4) 0.8313(4) -0.0618(3) 0.0386(13) Uani 1 1 d . . .
H16 H 0.7514 0.7670 -0.0773 0.046 Uiso 1 1 calc R . .
O17 O 0.9772(3) 0.7287(2) 0.68633(19) 0.0445(10) Uani 1 1 d . . .
C17 C 0.7092(4) 0.8413(4) 0.0108(3) 0.0315(12) Uani 1 1 d . . .
O18 O 1.2563(3) 0.2680(2) 0.62078(19) 0.0466(10) Uani 1 1 d . . .
H18O H 1.2449 0.2831 0.5770 0.056 Uiso 1 1 calc R . .
C18 C 0.6624(4) 0.9364(4) 0.0318(3) 0.0300(12) Uani 1 1 d . . .
O19 O 1.1781(3) 0.3830(2) 0.50601(18) 0.0376(9) Uani 1 1 d . . .
C19 C 0.6205(4) 1.0194(4) -0.0202(3) 0.0330(12) Uani 1 1 d . . .
H19 H 0.5882 1.0841 -0.0057 0.040 Uiso 1 1 calc R . .
O20 O 1.1026(3) 0.5465(2) 0.50789(18) 0.0429(10) Uani 1 1 d . . .
H20O H 1.1005 0.5469 0.4635 0.051 Uiso 1 1 calc R . .
C20 C 0.6559(4) 0.9499(4) 0.1088(3) 0.0320(12) Uani 1 1 d . . .
O21 O 1.0855(3) 0.5795(2) 0.37357(17) 0.0377(9) Uani 1 1 d . . .
N21 N 0.6870(3) 0.9276(3) 0.2981(2) 0.0386(11) Uani 1 1 d . . .
H21A H 0.6976 0.9039 0.2567 0.046 Uiso 1 1 calc R . .
H21B H 0.7112 0.8869 0.3373 0.046 Uiso 1 1 calc R . .
O22 O 0.9065(3) 0.9223(3) 0.10159(17) 0.0407(9) Uani 1 1 d . . .
H22O H 0.8872 0.9678 0.1276 0.049 Uiso 1 1 calc R . .
C22 C 0.6348(4) 1.0241(4) 0.3014(3) 0.0320(12) Uani 1 1 d . . .
O23 O 0.8908(3) 0.9997(3) 0.21628(18) 0.0389(9) Uani 1 1 d . . .
N23 N 0.6187(4) 1.0561(3) 0.3669(2) 0.0367(11) Uani 1 1 d . . .
H23 H 0.6477 1.0095 0.4022 0.044 Uiso 1 1 calc R . .
O24 O 0.9410(3) 0.8992(2) 0.31938(17) 0.0375(9) Uani 1 1 d . . .
H24O H 0.9174 0.9535 0.3359 0.045 Uiso 1 1 calc R . .
C24 C 0.5626(4) 1.1527(4) 0.3867(3) 0.0336(13) Uani 1 1 d . . .
C25 C 0.5445(5) 1.1630(4) 0.4615(3) 0.0404(14) Uani 1 1 d . . .
H25 H 0.5699 1.1055 0.4962 0.049 Uiso 1 1 calc R . .
C26 C 0.4909(4) 1.2541(4) 0.4858(3) 0.0393(14) Uani 1 1 d . . .
H26 H 0.4813 1.2591 0.5369 0.047 Uiso 1 1 calc R . .
C27 C 0.4501(4) 1.3398(4) 0.4369(3) 0.0341(13) Uani 1 1 d . . .
C28 C 0.4654(4) 1.3301(4) 0.3621(3) 0.0313(12) Uani 1 1 d . . .
C29 C 0.5222(4) 1.2374(4) 0.3373(3) 0.0317(12) Uani 1 1 d . . .
H29 H 0.5334 1.2320 0.2861 0.038 Uiso 1 1 calc R . .
C30 C 0.4218(4) 1.4191(4) 0.3085(3) 0.0312(12) Uani 1 1 d . . .
N31 N 0.8194(4) 1.1654(3) 0.3052(2) 0.0394(11) Uani 1 1 d . . .
H31A H 0.8403 1.1249 0.2718 0.047 Uiso 1 1 calc R . .
H31B H 0.7883 1.2299 0.2926 0.047 Uiso 1 1 calc R . .
C32 C 0.8349(4) 1.1289(4) 0.3749(3) 0.0318(12) Uani 1 1 d . . .
N33 N 0.8015(3) 1.1966(3) 0.4221(2) 0.0354(11) Uani 1 1 d . . .
H33 H 0.7741 1.2591 0.4028 0.042 Uiso 1 1 calc R . .
C34 C 0.8051(4) 1.1794(4) 0.4987(3) 0.0324(12) Uani 1 1 d . . .
C35 C 0.7705(4) 1.2630(4) 0.5339(3) 0.0355(13) Uani 1 1 d . . .
H35 H 0.7481 1.3267 0.5056 0.043 Uiso 1 1 calc R . .
C36 C 0.7680(4) 1.2550(4) 0.6082(3) 0.0398(14) Uani 1 1 d . . .
H36 H 0.7443 1.3129 0.6310 0.048 Uiso 1 1 calc R . .
C37 C 0.8002(4) 1.1620(4) 0.6508(3) 0.0352(13) Uani 1 1 d . . .
C38 C 0.8389(4) 1.0780(4) 0.6161(3) 0.0304(12) Uani 1 1 d . . .
C39 C 0.8404(4) 1.0872(4) 0.5401(3) 0.0315(12) Uani 1 1 d . . .
H39 H 0.8659 1.0295 0.5167 0.038 Uiso 1 1 calc R . .
C40 C 0.8753(4) 0.9795(4) 0.6596(3) 0.0337(13) Uani 1 1 d . . .
N41 N 0.9698(4) 0.7582(3) 0.8003(2) 0.0442(12) Uani 1 1 d . . .
H41A H 0.9277 0.8217 0.7907 0.053 Uiso 1 1 calc R . .
H41B H 0.9896 0.7344 0.8440 0.053 Uiso 1 1 calc R . .
C42 C 1.0036(5) 0.6976(4) 0.7484(3) 0.0382(13) Uani 1 1 d . . .
N43 N 1.0676(4) 0.6015(3) 0.7687(2) 0.0388(11) Uani 1 1 d . . .
H43 H 1.0821 0.5873 0.8139 0.047 Uiso 1 1 calc R . .
C44 C 1.1137(4) 0.5218(4) 0.7276(3) 0.0328(13) Uani 1 1 d . . .
C45 C 1.1709(4) 0.4268(4) 0.7634(3) 0.0358(13) Uani 1 1 d . . .
H45 H 1.1770 0.4198 0.8138 0.043 Uiso 1 1 calc R . .
C46 C 1.2181(4) 0.3440(4) 0.7273(3) 0.0401(14) Uani 1 1 d . . .
H46 H 1.2572 0.2809 0.7527 0.048 Uiso 1 1 calc R . .
C47 C 1.2093(4) 0.3517(4) 0.6550(3) 0.0331(13) Uani 1 1 d . . .
C48 C 1.1551(4) 0.4449(4) 0.6173(3) 0.0307(12) Uani 1 1 d . . .
C49 C 1.1083(4) 0.5287(4) 0.6538(3) 0.0326(12) Uani 1 1 d . . .
H49 H 1.0720 0.5920 0.6277 0.039 Uiso 1 1 calc R . .
C50 C 1.1470(4) 0.4549(4) 0.5387(3) 0.0311(12) Uani 1 1 d . . .
N51 N 1.1698(3) 0.4215(3) 0.3465(2) 0.0370(11) Uani 1 1 d . . .
H51A H 1.1777 0.3976 0.3928 0.044 Uiso 1 1 calc R . .
H51B H 1.1941 0.3809 0.3127 0.044 Uiso 1 1 calc R . .
C52 C 1.1211(4) 0.5193(4) 0.3274(3) 0.0312(12) Uani 1 1 d . . .
N53 N 1.1116(3) 0.5506(3) 0.2553(2) 0.0331(10) Uani 1 1 d . . .
H53 H 1.1436 0.5037 0.2259 0.040 Uiso 1 1 calc R . .
C54 C 1.0581(4) 0.6469(4) 0.2206(3) 0.0318(12) Uani 1 1 d . . .
C55 C 1.0434(4) 0.6569(4) 0.1485(3) 0.0353(13) Uani 1 1 d . . .
H55 H 1.0690 0.5990 0.1252 0.042 Uiso 1 1 calc R . .
C56 C 0.9927(4) 0.7485(4) 0.1097(3) 0.0365(13) Uani 1 1 d . . .
H56 H 0.9839 0.7531 0.0603 0.044 Uiso 1 1 calc R . .
C57 C 0.9552(4) 0.8325(4) 0.1418(3) 0.0322(12) Uani 1 1 d . . .
C58 C 0.9688(4) 0.8255(4) 0.2145(3) 0.0315(12) Uani 1 1 d . . .
C59 C 1.0207(4) 0.7315(4) 0.2532(3) 0.0304(12) Uani 1 1 d . . .
H59 H 1.0300 0.7263 0.3026 0.036 Uiso 1 1 calc R . .
C60 C 0.9301(4) 0.9156(4) 0.2502(3) 0.0337(13) Uani 1 1 d . . .
C61 C 0.0502(5) 2.0827(4) 0.0805(3) 0.0435(14) Uani 1 1 d . . .
H61A H 0.0192 2.0902 0.0367 0.065 Uiso 1 1 calc R . .
H61B H 0.0951 2.1223 0.0698 0.065 Uiso 1 1 calc R . .
H61C H -0.0123 2.1055 0.1227 0.065 Uiso 1 1 calc R . .
C62 C 0.1216(5) 1.9796(5) 0.0986(3) 0.0371(13) Uani 1 1 d . . .
N63 N 0.1758(4) 1.8987(4) 0.1133(3) 0.0455(12) Uani 1 1 d . . .
C64 C 0.6636(6) 0.8762(6) -0.3309(4) 0.073(2) Uani 1 1 d . . .
H64A H 0.7442 0.8435 -0.3279 0.109 Uiso 1 1 calc R . .
H64B H 0.6547 0.8751 -0.3808 0.109 Uiso 1 1 calc R . .
H64C H 0.6221 0.8411 -0.2939 0.109 Uiso 1 1 calc R . .
C65 C 0.6189(6) 0.9771(7) -0.3162(3) 0.064(2) Uani 1 1 d . . .
N66 N 0.5843(5) 1.0568(6) -0.3032(3) 0.0751(19) Uani 1 1 d . . .
C67 C 0.9426(5) 0.7842(4) 0.4843(3) 0.0461(15) Uani 1 1 d . . .
H67A H 0.9791 0.8296 0.4792 0.069 Uiso 1 1 calc R . .
H67B H 0.9800 0.7423 0.4440 0.069 Uiso 1 1 calc R . .
H67C H 0.9493 0.7424 0.5323 0.069 Uiso 1 1 calc R . .
C68 C 0.8236(5) 0.8410(4) 0.4804(3) 0.0398(14) Uani 1 1 d . . .
N69 N 0.7298(4) 0.8860(4) 0.4776(2) 0.0480(13) Uani 1 1 d . . .
C70 C 0.5371(5) 1.5887(4) 0.3720(3) 0.0455(15) Uani 1 1 d . . .
H70A H 0.4996 1.5967 0.4241 0.068 Uiso 1 1 calc R . .
H70B H 0.4797 1.6089 0.3415 0.068 Uiso 1 1 calc R . .
H70C H 0.5802 1.6302 0.3546 0.068 Uiso 1 1 calc R . .
C71 C 0.6133(5) 1.4863(5) 0.3662(3) 0.0382(14) Uani 1 1 d . . .
N72 N 0.6740(4) 1.4056(4) 0.3618(3) 0.0490(13) Uani 1 1 d . . .
C73 C 1.1671(5) 0.4511(4) 1.0213(3) 0.0516(16) Uani 1 1 d . . .
H73A H 1.2043 0.3942 0.9930 0.077 Uiso 1 1 calc R . .
H73B H 1.1130 0.4385 1.0647 0.077 Uiso 1 1 calc R . .
H73C H 1.2243 0.4613 1.0380 0.077 Uiso 1 1 calc R . .
C74 C 1.1072(5) 0.5388(5) 0.9746(3) 0.0429(14) Uani 1 1 d . . .
N75 N 1.0606(4) 0.6073(4) 0.9370(3) 0.0588(14) Uani 1 1 d . . .
C76 C 0.4527(4) 1.2828(4) 0.1146(3) 0.0432(14) Uani 1 1 d . . .
H76A H 0.4696 1.3396 0.0877 0.065 Uiso 1 1 calc R . .
H76B H 0.4622 1.2400 0.0789 0.065 Uiso 1 1 calc R . .
H76C H 0.5048 1.2451 0.1493 0.065 Uiso 1 1 calc R . .
C77 C 0.3368(5) 1.3179(4) 0.1556(3) 0.0377(13) Uani 1 1 d . . .
N78 N 0.2462(5) 1.3453(4) 0.1880(3) 0.0528(13) Uani 1 1 d . . .
O12 O 0.4369(3) 1.4006(2) 0.24087(17) 0.0386(9) Uani 1 1 d . . .
H12O H 0.4002 1.4526 0.2154 0.046 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.242(6) . ?
N1 C2 1.342(6) . ?
O2 C7 1.356(6) . ?
C2 N3 1.361(6) . ?
O3 C10 1.238(6) . ?
N3 C4 1.406(6) . ?
O4 C10 1.316(5) . ?
C4 C9 1.372(6) . ?
C4 C5 1.398(7) . ?
O5 C12 1.248(6) . ?
C5 C6 1.368(7) . ?
O6 C17 1.363(6) . ?
C6 C7 1.392(7) . ?
O7 C20 1.230(6) . ?
C7 C8 1.407(7) . ?
O8 C20 1.300(6) . ?
C8 C9 1.399(6) . ?
C8 C10 1.465(7) . ?
O9 C22 1.255(6) . ?
O10 C27 1.358(6) . ?
O11 C30 1.230(6) . ?
N11 C12 1.352(6) . ?
C12 N13 1.346(6) . ?
O13 C32 1.247(6) . ?
N13 C14 1.403(6) . ?
O14 C37 1.358(6) . ?
C14 C19 1.374(7) . ?
C14 C15 1.396(7) . ?
O15 C40 1.234(6) . ?
C15 C16 1.358(7) . ?
O16 C40 1.306(6) . ?
C16 C17 1.379(7) . ?
O17 C42 1.238(6) . ?
C17 C18 1.397(7) . ?
O18 C47 1.364(6) . ?
C18 C19 1.403(7) . ?
C18 C20 1.481(7) . ?
O19 C50 1.226(6) . ?
O20 C50 1.307(6) . ?
O21 C52 1.249(5) . ?
N21 C22 1.322(6) . ?
O22 C57 1.366(6) . ?
C22 N23 1.352(6) . ?
O23 C60 1.236(6) . ?
N23 C24 1.404(6) . ?
O24 C60 1.303(6) . ?
C24 C29 1.386(7) . ?
C24 C25 1.394(7) . ?
C25 C26 1.364(7) . ?
C26 C27 1.392(7) . ?
C27 C28 1.396(6) . ?
C28 C29 1.388(7) . ?
C28 C30 1.477(7) . ?
C30 O12 1.307(6) . ?
N31 C32 1.336(6) . ?
C32 N33 1.352(6) . ?
N33 C34 1.413(6) . ?
C34 C39 1.380(7) . ?
C34 C35 1.395(7) . ?
C35 C36 1.368(7) . ?
C36 C37 1.398(7) . ?
C37 C38 1.388(7) . ?
C38 C39 1.399(6) . ?
C38 C40 1.469(7) . ?
N41 C42 1.340(6) . ?
C42 N43 1.350(6) . ?
N43 C44 1.393(6) . ?
C44 C49 1.385(6) . ?
C44 C45 1.406(7) . ?
C45 C46 1.373(7) . ?
C46 C47 1.370(7) . ?
C47 C48 1.394(7) . ?
C48 C49 1.390(7) . ?
C48 C50 1.477(7) . ?
N51 C52 1.336(6) . ?
C52 N53 1.351(6) . ?
N53 C54 1.402(6) . ?
C54 C59 1.375(7) . ?
C54 C55 1.386(7) . ?
C55 C56 1.378(7) . ?
C56 C57 1.361(7) . ?
C57 C58 1.400(7) . ?
C58 C59 1.404(7) . ?
C58 C60 1.477(7) . ?
C61 C62 1.444(8) . ?
C62 N63 1.128(6) . ?
C64 C65 1.437(10) . ?
C65 N66 1.144(9) . ?
C67 C68 1.451(8) . ?
C68 N69 1.143(7) . ?
C70 C71 1.442(8) . ?
C71 N72 1.137(6) . ?
C73 C74 1.446(8) . ?
C74 N75 1.140(7) . ?
C76 C77 1.449(8) . ?
C77 N78 1.135(6) . ?

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
O1 C2 N1 122.2(5) . . ?
O1 C2 N3 122.8(4) . . ?
N1 C2 N3 115.1(5) . . ?
C2 N3 C4 128.5(4) . . ?
C9 C4 C5 118.6(4) . . ?
C9 C4 N3 124.7(4) . . ?
C5 C4 N3 116.7(4) . . ?
C6 C5 C4 121.5(5) . . ?
C5 C6 C7 120.3(5) . . ?
O2 C7 C6 118.3(4) . . ?
O2 C7 C8 122.9(5) . . ?
C6 C7 C8 118.9(5) . . ?
C9 C8 C7 119.6(5) . . ?
C9 C8 C10 120.7(4) . . ?
C7 C8 C10 119.7(4) . . ?
C4 C9 C8 121.0(5) . . ?
O3 C10 O4 122.2(5) . . ?
O3 C10 C8 123.4(4) . . ?
O4 C10 C8 114.4(4) . . ?
O5 C12 N13 122.5(5) . . ?
O5 C12 N11 121.3(5) . . ?
N13 C12 N11 116.2(4) . . ?
C12 N13 C14 129.3(4) . . ?
C19 C14 C15 118.4(5) . . ?
C19 C14 N13 124.1(5) . . ?
C15 C14 N13 117.4(4) . . ?
C16 C15 C14 121.5(5) . . ?
C15 C16 C17 120.9(5) . . ?
O6 C17 C16 118.5(4) . . ?
O6 C17 C18 122.7(4) . . ?
C16 C17 C18 118.8(5) . . ?
C17 C18 C19 119.9(4) . . ?
C17 C18 C20 120.2(4) . . ?
C19 C18 C20 119.9(4) . . ?
C14 C19 C18 120.4(5) . . ?
O7 C20 O8 123.8(4) . . ?
O7 C20 C18 121.7(5) . . ?
O8 C20 C18 114.6(4) . . ?
O9 C22 N21 121.5(4) . . ?
O9 C22 N23 121.1(5) . . ?
N21 C22 N23 117.4(4) . . ?
C22 N23 C24 129.4(4) . . ?
C29 C24 C25 118.4(5) . . ?
C29 C24 N23 124.4(4) . . ?
C25 C24 N23 117.1(5) . . ?
C26 C25 C24 121.2(5) . . ?
C25 C26 C27 121.0(5) . . ?
O10 C27 C26 118.7(4) . . ?
O10 C27 C28 123.1(5) . . ?
C26 C27 C28 118.2(5) . . ?
C29 C28 C27 120.6(5) . . ?
C29 C28 C30 119.5(4) . . ?
C27 C28 C30 119.9(4) . . ?
C24 C29 C28 120.5(4) . . ?
O11 C30 O12 122.9(5) . . ?
O11 C30 C28 122.7(4) . . ?
O12 C30 C28 114.5(4) . . ?
O13 C32 N31 121.9(4) . . ?
O13 C32 N33 122.1(4) . . ?
N31 C32 N33 116.0(4) . . ?
C32 N33 C34 128.1(4) . . ?
C39 C34 C35 118.6(5) . . ?
C39 C34 N33 124.9(4) . . ?
C35 C34 N33 116.5(4) . . ?
C36 C35 C34 121.3(5) . . ?
C35 C36 C37 120.3(5) . . ?
O14 C37 C38 123.4(5) . . ?
O14 C37 C36 117.6(4) . . ?
C38 C37 C36 119.0(5) . . ?
C37 C38 C39 120.1(5) . . ?
C37 C38 C40 119.9(4) . . ?
C39 C38 C40 120.0(4) . . ?
C34 C39 C38 120.6(5) . . ?
O15 C40 O16 122.8(5) . . ?
O15 C40 C38 122.6(4) . . ?
O16 C40 C38 114.6(4) . . ?
O17 C42 N41 121.6(5) . . ?
O17 C42 N43 122.9(5) . . ?
N41 C42 N43 115.4(5) . . ?
C42 N43 C44 128.6(4) . . ?
C49 C44 N43 125.1(4) . . ?
C49 C44 C45 117.2(5) . . ?
N43 C44 C45 117.7(4) . . ?
C46 C45 C44 121.6(5) . . ?
C47 C46 C45 120.5(5) . . ?
O18 C47 C46 119.1(4) . . ?
O18 C47 C48 121.4(4) . . ?
C46 C47 C48 119.5(5) . . ?
C49 C48 C47 119.8(5) . . ?
C49 C48 C50 119.9(5) . . ?
C47 C48 C50 120.2(4) . . ?
C44 C49 C48 121.4(5) . . ?
O19 C50 O20 123.2(4) . . ?
O19 C50 C48 122.4(5) . . ?
O20 C50 C48 114.4(4) . . ?
O21 C52 N51 122.0(4) . . ?
O21 C52 N53 121.2(4) . . ?
N51 C52 N53 116.7(4) . . ?
C52 N53 C54 129.4(4) . . ?
C59 C54 C55 118.2(5) . . ?
C59 C54 N53 124.2(4) . . ?
C55 C54 N53 117.6(4) . . ?
C56 C55 C54 121.7(5) . . ?
C57 C56 C55 120.3(5) . . ?
C56 C57 O22 118.9(4) . . ?
C56 C57 C58 119.7(5) . . ?
O22 C57 C58 121.3(4) . . ?
C57 C58 C59 119.2(4) . . ?
C57 C58 C60 120.7(5) . . ?
C59 C58 C60 120.1(4) . . ?
C54 C59 C58 120.9(4) . . ?
O23 C60 O24 123.3(5) . . ?
O23 C60 C58 121.9(4) . . ?
O24 C60 C58 114.8(4) . . ?
N63 C62 C61 178.8(6) . . ?
N66 C65 C64 178.6(8) . . ?
N69 C68 C67 179.6(6) . . ?
N72 C71 C70 179.5(6) . . ?
N75 C74 C73 179.2(6) . . ?
N78 C77 C76 179.7(5) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        23.34
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.070
####################################################################### 
# 
# 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_Acetone
_database_code_depnum_ccdc_archive 'CCDC 1495378'
_audit_update_record             
;
2016-07-22 deposited with the CCDC.
2016-09-01 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         ?
_chemical_formula_sum            'C11 H14 N2 O5'
_chemical_formula_weight         254.24

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   14.6759(9)
_cell_length_b                   31.2850(19)
_cell_length_c                   15.9269(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.324(2)
_cell_angle_gamma                90
_cell_volume                     7216.0(8)
_cell_formula_units_Z            24
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    132
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      18.93

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_F_000             3216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.328
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.066
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            63443
_diffrn_reflns_av_unetI/netI     0.0710
_diffrn_reflns_av_R_equivalents  0.1104
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.061
_diffrn_reflns_theta_max         22.070
_diffrn_reflns_theta_full        22.070
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             8899
_reflns_number_gt                5728
_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 SAINT'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        ?
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    XSeed
_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)+(0.0922P)²+19.1814P] 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_number_reflns         8899
_refine_ls_number_parameters     985
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1293
_refine_ls_R_factor_gt           0.0790
_refine_ls_wR_factor_ref         0.2110
_refine_ls_wR_factor_gt          0.1799
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.056
_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 0.6533(3) 0.15455(11) 0.3140(3) 0.0284(10) Uani 1 1 d . . . . .
N1 N 0.6718(3) 0.22576(14) 0.3032(3) 0.0285(13) Uani 1 1 d . . . . .
H1A H 0.7237 0.2221 0.2830 0.034 Uiso 1 1 calc R U . . .
H1B H 0.6512 0.2517 0.3099 0.034 Uiso 1 1 calc R U . . .
O2 O 0.2887(3) 0.09276(12) 0.4674(2) 0.0303(10) Uani 1 1 d . . . . .
H2O H 0.3001 0.0669 0.4593 0.036 Uiso 1 1 calc R U . . .
C2 C 0.6244(4) 0.19186(18) 0.3235(4) 0.0258(15) Uani 1 1 d . . . . .
O3 O 0.3865(3) 0.02839(12) 0.4287(2) 0.0231(9) Uani 1 1 d . . . . .
N3 N 0.5475(3) 0.20008(14) 0.3556(3) 0.0256(12) Uani 1 1 d . U . . .
H3 H 0.5343 0.2273 0.3605 0.031 Uiso 1 1 calc R U . . .
O4 O 0.5056(2) 0.04056(11) 0.3610(2) 0.0235(10) Uani 1 1 d . . . . .
H4O H 0.5075 0.0137 0.3608 0.028 Uiso 1 1 calc R U . . .
C4 C 0.4852(4) 0.17122(17) 0.3825(4) 0.0214(14) Uani 1 1 d . . . . .
O5 O 0.5402(2) -0.03818(11) 0.3525(2) 0.0223(10) Uani 1 1 d . . . . .
C5 C 0.4113(4) 0.18746(19) 0.4176(4) 0.0301(16) Uani 1 1 d . . . . .
H5 H 0.4047 0.2175 0.4223 0.036 Uiso 1 1 calc R U . . .
O6 O 0.8172(3) -0.18001(11) 0.2345(2) 0.0256(10) Uani 1 1 d . . . . .
H6O H 0.8524 -0.1611 0.2202 0.031 Uiso 1 1 calc R U . . .
C6 C 0.3486(4) 0.16144(18) 0.4450(4) 0.0245(15) Uani 1 1 d . . . . .
H6 H 0.2999 0.1738 0.4694 0.029 Uiso 1 1 calc R U . . .
O7 O 0.8734(3) -0.10233(11) 0.2139(2) 0.0219(9) Uani 1 1 d . . . . .
C7 C 0.3533(4) 0.11779(18) 0.4387(3) 0.0182(13) Uani 1 1 d . . . . .
O8 O 0.7867(3) -0.04757(11) 0.2467(2) 0.0241(10) Uani 1 1 d . . . . .
H8O H 0.8275 -0.0332 0.2279 0.029 Uiso 1 1 calc R U . . .
C8 C 0.4261(4) 0.10007(17) 0.4043(3) 0.0186(13) Uani 1 1 d . . . . .
O9 O 0.8818(3) 0.00669(12) 0.1797(3) 0.0271(10) Uani 1 1 d . . . . .
C9 C 0.4909(4) 0.12659(17) 0.3752(3) 0.0200(14) Uani 1 1 d . . . . .
H9 H 0.5393 0.1143 0.3501 0.024 Uiso 1 1 calc R U . . .
O10 O 0.9487(3) 0.20845(13) 0.1134(3) 0.0484(13) Uani 1 1 d . . . . .
H10O H 0.9067 0.2161 0.1403 0.058 Uiso 1 1 calc R U . . .
C10 C 0.4370(4) 0.05338(18) 0.3993(4) 0.0202(14) Uani 1 1 d . . . . .
O11 O 0.8221(3) 0.19766(13) 0.2096(3) 0.0313(10) Uani 1 1 d . . . . .
N11 N 0.4277(3) -0.06289(14) 0.4205(3) 0.0216(11) Uani 1 1 d . . . . .
H11A H 0.4070 -0.0369 0.4270 0.026 Uiso 1 1 calc R U . . .
H11B H 0.4005 -0.0850 0.4401 0.026 Uiso 1 1 calc R U . . .
O12 O 0.7863(3) 0.13112(11) 0.2422(2) 0.0257(10) Uani 1 1 d . . . . .
H12O H 0.7472 0.1439 0.2661 0.031 Uiso 1 1 calc R U . . .
C12 C 0.4990(4) -0.06868(17) 0.3816(3) 0.0145(13) Uani 1 1 d . . . . .
O13 O 0.8635(3) 0.32156(12) 0.6736(3) 0.0303(10) Uani 1 1 d . . . . .
N13 N 0.5253(3) -0.10990(14) 0.3715(3) 0.0179(11) Uani 1 1 d . . . . .
H13 H 0.4902 -0.1296 0.3895 0.021 Uiso 1 1 calc R U . . .
O14 O 1.2239(3) 0.25202(12) 0.5215(3) 0.0288(10) Uani 1 1 d . . . . .
H14O H 1.2100 0.2263 0.5273 0.035 Uiso 1 1 calc R U . . .
C14 C 0.6012(3) -0.12543(16) 0.3361(3) 0.0144(13) Uani 1 1 d . . . . .
O15 O 1.1244(3) 0.18891(11) 0.5622(2) 0.0232(9) Uani 1 1 d . . . . .
C15 C 0.6107(4) -0.16937(16) 0.3285(3) 0.0169(13) Uani 1 1 d . . . . .
H15 H 0.5661 -0.1876 0.3468 0.020 Uiso 1 1 calc R U . . .
O16 O 0.9969(3) 0.20270(11) 0.6166(3) 0.0272(10) Uani 1 1 d . . . . .
H16O H 0.9937 0.1759 0.6163 0.033 Uiso 1 1 calc R U . . .
C16 C 0.6817(4) -0.18700(17) 0.2955(4) 0.0220(14) Uani 1 1 d . . . . .
H16 H 0.6865 -0.2172 0.2916 0.026 Uiso 1 1 calc R U . . .
O17 O 0.6225(3) 0.17416(11) 0.7995(3) 0.0291(10) Uani 1 1 d . . . . .
C17 C 0.7473(4) -0.16109(17) 0.2676(3) 0.0167(13) Uani 1 1 d . . . . .
O18 O 0.5553(3) 0.37863(11) 0.8543(3) 0.0331(11) Uani 1 1 d . . . . .
H18O H 0.5996 0.3857 0.8299 0.040 Uiso 1 1 calc R U . . .
C18 C 0.7397(3) -0.11703(16) 0.2742(3) 0.0138(13) Uani 1 1 d . . . . .
O19 O 0.6923(3) 0.36544(11) 0.7703(3) 0.0277(10) Uani 1 1 d . . . . .
C19 C 0.6662(4) -0.09948(17) 0.3095(3) 0.0162(13) Uani 1 1 d . . . . .
H19 H 0.6615 -0.0694 0.3150 0.019 Uiso 1 1 calc R U . . .
O20 O 0.7278(3) 0.29790(12) 0.7403(3) 0.0300(10) Uani 1 1 d . . . . .
H20O H 0.7681 0.3104 0.7173 0.036 Uiso 1 1 calc R U . . .
C20 C 0.8062(4) -0.08859(17) 0.2431(3) 0.0170(13) Uani 1 1 d . . . . .
O21 O 0.9613(2) 0.12350(11) 0.6225(3) 0.0245(10) Uani 1 1 d . . . . .
N21 N 0.9808(3) -0.03930(15) 0.1326(3) 0.0301(13) Uani 1 1 d . . . . .
H21A H 0.9501 -0.0616 0.1469 0.036 Uiso 1 1 calc R U . . .
H21B H 1.0305 -0.0430 0.1091 0.036 Uiso 1 1 calc R U . . .
O22 O 0.6902(3) -0.01380(11) 0.7676(2) 0.0248(10) Uani 1 1 d . . . . .
H22O H 0.6568 0.0056 0.7830 0.030 Uiso 1 1 calc R U . . .
C22 C 0.9513(4) 0.00079(18) 0.1468(4) 0.0217(14) Uani 1 1 d . . . . .
O23 O 0.6412(3) 0.06456(11) 0.7911(2) 0.0214(9) Uani 1 1 d . . . . .
N23 N 1.0022(3) 0.03219(14) 0.1228(3) 0.0207(11) Uani 1 1 d . . . . .
H23 H 1.0525 0.0243 0.1034 0.025 Uiso 1 1 calc R U . . .
O24 O 0.7194(2) 0.11831(11) 0.7435(2) 0.0238(10) Uani 1 1 d . . . . .
H24O H 0.6801 0.1329 0.7637 0.029 Uiso 1 1 calc R U . . .
C24 C 0.9855(4) 0.07708(18) 0.1246(4) 0.0233(14) Uani 1 1 d . . . . .
O25 O 0.5045(3) 0.04549(13) 0.1143(3) 0.0458(13) Uani 1 1 d . . . . .
C25 C 1.0368(4) 0.1035(2) 0.0810(4) 0.0372(17) Uani 1 1 d . . . . .
H25 H 1.0815 0.0910 0.0515 0.045 Uiso 1 1 calc R U . . .
O26 O 0.6241(3) 0.15110(14) 0.5587(3) 0.0355(11) Uani 1 1 d . . . . .
C26 C 1.0259(4) 0.1465(2) 0.0785(4) 0.0396(18) Uani 1 1 d . . . . .
H26 H 1.0637 0.1637 0.0490 0.047 Uiso 1 1 calc R U . . .
O27 O 1.1489(3) -0.02188(15) 0.0643(3) 0.0407(12) Uani 1 1 d . . . . .
C27 C 0.9594(4) 0.16563(19) 0.1192(4) 0.0326(16) Uani 1 1 d . . . . .
O28 O 0.3680(3) 0.15606(15) 0.9313(3) 0.0408(12) Uani 1 1 d . . . . .
C28 C 0.9059(4) 0.13972(18) 0.1641(4) 0.0241(14) Uani 1 1 d . . . . .
O29 O 0.5175(3) 0.29073(12) 0.3649(3) 0.0295(10) Uani 1 1 d . . . . .
C29 C 0.9209(4) 0.09540(18) 0.1668(3) 0.0214(14) Uani 1 1 d . . . . .
H29 H 0.8858 0.0778 0.1982 0.026 Uiso 1 1 calc R U . . .
O30 O 1.1260(3) 0.00326(13) 0.5619(3) 0.0334(11) Uani 1 1 d . . . . .
C30 C 0.8344(4) 0.15862(19) 0.2083(4) 0.0249(15) Uani 1 1 d . . . . .
N31 N 0.8521(3) 0.39241(14) 0.6874(3) 0.0290(13) Uani 1 1 d . . . . .
H31A H 0.7987 0.3903 0.7054 0.035 Uiso 1 1 calc R U . . .
H31B H 0.8769 0.4177 0.6824 0.035 Uiso 1 1 calc R U . . .
C32 C 0.8961(4) 0.35677(19) 0.6673(4) 0.0233(14) Uani 1 1 d . . . . .
N33 N 0.9757(3) 0.36365(14) 0.6345(3) 0.0218(12) Uani 1 1 d . . . . .
H33 H 0.9924 0.3905 0.6305 0.026 Uiso 1 1 calc R U . . .
C34 C 1.0331(4) 0.33306(17) 0.6068(4) 0.0213(14) Uani 1 1 d . . . . .
C35 C 1.1080(4) 0.34805(18) 0.5722(4) 0.0301(16) Uani 1 1 d . . . . .
H35 H 1.1165 0.3780 0.5671 0.036 Uiso 1 1 calc R U . . .
C36 C 1.1701(4) 0.32052(18) 0.5453(4) 0.0244(14) Uani 1 1 d . . . . .
H36 H 1.2216 0.3318 0.5234 0.029 Uiso 1 1 calc R U . . .
C37 C 1.1595(4) 0.27768(18) 0.5495(4) 0.0214(14) Uani 1 1 d . . . . .
C38 C 1.0843(4) 0.26114(16) 0.5829(4) 0.0191(14) Uani 1 1 d . . . . .
C39 C 1.0207(4) 0.28950(17) 0.6113(4) 0.0210(14) Uani 1 1 d . . . . .
H39 H 0.9693 0.2785 0.6337 0.025 Uiso 1 1 calc R U . . .
C40 C 1.0703(4) 0.21462(17) 0.5862(3) 0.0171(13) Uani 1 1 d . . . . .
N41 N 0.5299(3) 0.13011(14) 0.8587(3) 0.0239(12) Uani 1 1 d . . . . .
H41A H 0.5587 0.1074 0.8435 0.029 Uiso 1 1 calc R U . . .
H41B H 0.4834 0.1270 0.8868 0.029 Uiso 1 1 calc R U . . .
C42 C 0.5569(4) 0.16932(18) 0.8392(4) 0.0223(14) Uani 1 1 d . . . . .
N43 N 0.5100(3) 0.20275(14) 0.8655(3) 0.0207(11) Uani 1 1 d . . . . .
H43 H 0.4635 0.1959 0.8915 0.025 Uiso 1 1 calc R U . . .
C44 C 0.5249(4) 0.24635(18) 0.8574(3) 0.0187(13) Uani 1 1 d . . . . .
C45 C 0.4669(4) 0.27364(18) 0.8919(4) 0.0243(14) Uani 1 1 d . . . . .
H45 H 0.4185 0.2619 0.9178 0.029 Uiso 1 1 calc R U . . .
C46 C 0.4773(4) 0.31757(19) 0.8900(4) 0.0285(15) Uani 1 1 d . . . . .
H46 H 0.4363 0.3355 0.9144 0.034 Uiso 1 1 calc R U . . .
C47 C 0.5465(4) 0.33547(19) 0.8530(4) 0.0239(15) Uani 1 1 d . . . . .
C48 C 0.6054(4) 0.30856(17) 0.8156(4) 0.0194(14) Uani 1 1 d . . . . .
C49 C 0.5930(4) 0.26416(17) 0.8186(4) 0.0228(14) Uani 1 1 d . . . . .
H49 H 0.6326 0.2459 0.7932 0.027 Uiso 1 1 calc R U . . .
C50 C 0.6778(4) 0.32684(18) 0.7740(4) 0.0246(15) Uani 1 1 d . . . . .
N51 N 1.0823(3) 0.09548(14) 0.5693(3) 0.0242(12) Uani 1 1 d . . . . .
H51A H 1.1030 0.1209 0.5579 0.029 Uiso 1 1 calc R U . . .
H51B H 1.1119 0.0723 0.5576 0.029 Uiso 1 1 calc R U . . .
C52 C 1.0062(4) 0.09211(18) 0.6044(4) 0.0205(14) Uani 1 1 d . . . . .
N53 N 0.9795(3) 0.05082(14) 0.6192(3) 0.0225(12) Uani 1 1 d . . . . .
H53 H 1.0144 0.0304 0.6035 0.027 Uiso 1 1 calc R U . . .
C54 C 0.9035(4) 0.03717(16) 0.6562(3) 0.0149(13) Uani 1 1 d . . . . .
C55 C 0.8917(4) -0.00665(17) 0.6656(4) 0.0238(15) Uani 1 1 d . . . . .
H55 H 0.9342 -0.0258 0.6463 0.029 Uiso 1 1 calc R U . . .
C56 C 0.8219(4) -0.02276(18) 0.7012(4) 0.0219(14) Uani 1 1 d . . . . .
H56 H 0.8158 -0.0529 0.7061 0.026 Uiso 1 1 calc R U . . .
C57 C 0.7585(4) 0.00407(17) 0.7311(3) 0.0197(14) Uani 1 1 d . . . . .
C58 C 0.7686(4) 0.04831(17) 0.7218(3) 0.0176(13) Uani 1 1 d . . . . .
C59 C 0.8403(3) 0.06440(16) 0.6840(3) 0.0117(12) Uani 1 1 d . U . . .
H59 H 0.8461 0.0944 0.6771 0.014 Uiso 1 1 calc R U . . .
C60 C 0.7039(4) 0.07749(17) 0.7546(4) 0.0185(14) Uani 1 1 d . . . . .
C61 C 0.5576(4) -0.02512(17) 0.1399(4) 0.0283(15) Uani 1 1 d . . . . .
H61A H 0.5263 -0.0381 0.1834 0.042 Uiso 1 1 calc R U . . .
H61B H 0.6201 -0.0369 0.1444 0.042 Uiso 1 1 calc R U . . .
H61C H 0.5229 -0.0314 0.0833 0.042 Uiso 1 1 calc R U . . .
C62 C 0.5631(4) 0.02214(18) 0.1529(4) 0.0252(15) Uani 1 1 d . . . . .
C63 C 0.6419(4) 0.03878(19) 0.2152(4) 0.0352(17) Uani 1 1 d . . . . .
H63A H 0.6978 0.0392 0.1889 0.053 Uiso 1 1 calc R U . . .
H63B H 0.6518 0.0202 0.2654 0.053 Uiso 1 1 calc R U . . .
H63C H 0.6278 0.0678 0.2323 0.053 Uiso 1 1 calc R U . . .
C64 C 0.7591(4) 0.1833(2) 0.5306(5) 0.0456(19) Uani 1 1 d . . . . .
H64A H 0.7854 0.1544 0.5372 0.068 Uiso 1 1 calc R U . . .
H64B H 0.8004 0.2034 0.5653 0.068 Uiso 1 1 calc R U . . .
H64C H 0.7521 0.1918 0.4706 0.068 Uiso 1 1 calc R U . . .
C65 C 0.6676(4) 0.18360(19) 0.5586(3) 0.0218(14) Uani 1 1 d . . . . .
C66 C 0.6310(5) 0.2242(2) 0.5848(5) 0.053(2) Uani 1 1 d . . . . .
H66A H 0.6119 0.2421 0.5346 0.080 Uiso 1 1 calc R U . . .
H66B H 0.6790 0.2390 0.6243 0.080 Uiso 1 1 calc R U . . .
H66C H 0.5777 0.2186 0.6131 0.080 Uiso 1 1 calc R U . . .
C67 C 1.2357(5) -0.0776(2) 0.0149(4) 0.0438(19) Uani 1 1 d . . . . .
H67A H 1.1849 -0.0957 0.0271 0.066 Uiso 1 1 calc R U . . .
H67B H 1.2934 -0.0868 0.0502 0.066 Uiso 1 1 calc R U . . .
H67C H 1.2414 -0.0803 -0.0453 0.066 Uiso 1 1 calc R U . . .
C68 C 1.2165(4) -0.0321(2) 0.0345(4) 0.0322(16) Uani 1 1 d . . . . .
C69 C 1.2818(5) 0.0013(3) 0.0164(5) 0.062(2) Uani 1 1 d . . . . .
H69A H 1.2726 0.0272 0.0487 0.093 Uiso 1 1 calc R U . . .
H69B H 1.2707 0.0079 -0.0446 0.093 Uiso 1 1 calc R U . . .
H69C H 1.3452 -0.0089 0.0330 0.093 Uiso 1 1 calc R U . . .
C70 C 0.2497(5) 0.1969(3) 0.9758(5) 0.066(3) Uani 1 1 d . . . . .
H70A H 0.2763 0.2209 0.9483 0.099 Uiso 1 1 calc R U . . .
H70B H 0.2582 0.2018 1.0373 0.099 Uiso 1 1 calc R U . . .
H70C H 0.1837 0.1947 0.9533 0.099 Uiso 1 1 calc R U . . .
C71 C 0.2968(5) 0.1567(2) 0.9581(4) 0.0356(17) Uani 1 1 d . . . . .
C72 C 0.2506(5) 0.1166(3) 0.9753(5) 0.068(3) Uani 1 1 d . . . . .
H72A H 0.1897 0.1153 0.9395 0.102 Uiso 1 1 calc R U . . .
H72B H 0.2433 0.1157 1.0354 0.102 Uiso 1 1 calc R U . . .
H72C H 0.2880 0.0923 0.9625 0.102 Uiso 1 1 calc R U . . .
C73 C 0.4383(4) 0.35645(18) 0.3477(5) 0.0386(17) Uani 1 1 d . . . . .
H73A H 0.4899 0.3661 0.3904 0.058 Uiso 1 1 calc R U . . .
H73B H 0.3799 0.3622 0.3680 0.058 Uiso 1 1 calc R U . . .
H73C H 0.4393 0.3718 0.2942 0.058 Uiso 1 1 calc R U . . .
C74 C 0.4472(4) 0.30982(18) 0.3333(4) 0.0253(15) Uani 1 1 d . . . . .
C75 C 0.3683(5) 0.2880(2) 0.2785(5) 0.0441(18) Uani 1 1 d . . . . .
H75A H 0.3214 0.2802 0.3130 0.066 Uiso 1 1 calc R U . . .
H75B H 0.3907 0.2621 0.2537 0.066 Uiso 1 1 calc R U . . .
H75C H 0.3413 0.3073 0.2327 0.066 Uiso 1 1 calc R U . . .
C76 C 1.2650(4) -0.0283(2) 0.5418(4) 0.0412(18) Uani 1 1 d . . . . .
H76A H 1.2609 -0.0303 0.4799 0.062 Uiso 1 1 calc R U . . .
H76B H 1.3012 -0.0523 0.5689 0.062 Uiso 1 1 calc R U . . .
H76C H 1.2951 -0.0013 0.5616 0.062 Uiso 1 1 calc R U . . .
C77 C 1.1709(4) -0.02951(18) 0.5643(4) 0.0204(14) Uani 1 1 d . . . . .
C78 C 1.1334(5) -0.0707(2) 0.5860(5) 0.0429(18) Uani 1 1 d . . . . .
H78A H 1.0685 -0.0672 0.5923 0.064 Uiso 1 1 calc R U . . .
H78B H 1.1687 -0.0812 0.6395 0.064 Uiso 1 1 calc R U . . .
H78C H 1.1379 -0.0914 0.5405 0.064 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 1.260(7) . ?
N1 C2 1.337(7) . ?
O2 C7 1.364(6) . ?
C2 N3 1.337(7) . ?
O3 C10 1.222(6) . ?
N3 C4 1.401(7) . ?
O4 C10 1.321(6) . ?
C4 C5 1.394(8) . ?
C4 C9 1.405(8) . ?
O5 C12 1.258(6) . ?
C5 C6 1.352(8) . ?
O6 C17 1.362(6) . ?
C6 C7 1.372(8) . ?
O7 C20 1.235(6) . ?
C7 C8 1.393(7) . ?
O8 C20 1.318(6) . ?
C8 C9 1.396(8) . ?
C8 C10 1.473(8) . ?
O9 C22 1.233(6) . ?
O10 C27 1.350(7) . ?
O11 C30 1.235(7) . ?
N11 C12 1.312(7) . ?
O12 C30 1.287(7) . ?
C12 N13 1.363(7) . ?
O13 C32 1.211(7) . ?
N13 C14 1.414(6) . ?
O14 C37 1.368(6) . ?
C14 C19 1.371(7) . ?
C14 C15 1.389(7) . ?
O15 C40 1.233(6) . ?
C15 C16 1.358(7) . ?
O16 C40 1.305(6) . ?
C16 C17 1.385(7) . ?
O17 C42 1.244(7) . ?
C17 C18 1.388(7) . ?
O18 C47 1.356(7) . ?
C18 C19 1.407(7) . ?
C18 C20 1.464(7) . ?
O19 C50 1.229(7) . ?
O20 C50 1.332(7) . ?
O21 C52 1.241(7) . ?
N21 C22 1.358(7) . ?
O22 C57 1.359(6) . ?
C22 N23 1.327(7) . ?
O23 C60 1.233(6) . ?
N23 C24 1.427(7) . ?
O24 C60 1.314(6) . ?
C24 C29 1.374(8) . ?
C24 C25 1.379(8) . ?
O25 C62 1.216(7) . ?
C25 C26 1.356(9) . ?
O26 C65 1.200(7) . ?
C26 C27 1.390(9) . ?
O27 C68 1.211(7) . ?
C27 C28 1.403(8) . ?
O28 C71 1.192(7) . ?
C28 C29 1.403(8) . ?
C28 C30 1.478(8) . ?
O29 C74 1.227(7) . ?
O30 C77 1.216(6) . ?
N31 C32 1.352(7) . ?
C32 N33 1.372(7) . ?
N33 C34 1.393(7) . ?
C34 C39 1.378(7) . ?
C34 C35 1.389(8) . ?
C35 C36 1.371(8) . ?
C36 C37 1.352(8) . ?
C37 C38 1.400(8) . ?
C38 C39 1.414(8) . ?
C38 C40 1.472(8) . ?
N41 C42 1.341(7) . ?
C42 N43 1.355(7) . ?
N43 C44 1.391(7) . ?
C44 C49 1.376(8) . ?
C44 C45 1.381(8) . ?
C45 C46 1.383(8) . ?
C46 C47 1.374(8) . ?
C47 C48 1.406(8) . ?
C48 C49 1.403(8) . ?
C48 C50 1.457(8) . ?
N51 C52 1.333(7) . ?
C52 N53 1.381(7) . ?
N53 C54 1.409(7) . ?
C54 C59 1.384(7) . ?
C54 C55 1.393(7) . ?
C55 C56 1.347(8) . ?
C56 C57 1.392(8) . ?
C57 C58 1.402(8) . ?
C58 C59 1.390(7) . ?
C58 C60 1.473(7) . ?
C61 C62 1.493(8) . ?
C62 C63 1.490(8) . ?
C64 C65 1.483(8) . ?
C65 C66 1.466(9) . ?
C67 C68 1.494(9) . ?
C68 C69 1.479(9) . ?
C70 C71 1.484(9) . ?
C71 C72 1.472(10) . ?
C73 C74 1.486(8) . ?
C74 C75 1.498(8) . ?
C76 C77 1.483(8) . ?
C77 C78 1.465(8) . ?

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
O1 C2 N3 123.1(5) . . ?
O1 C2 N1 120.5(6) . . ?
N3 C2 N1 116.4(5) . . ?
C2 N3 C4 128.8(5) . . ?
C5 C4 N3 118.5(5) . . ?
C5 C4 C9 117.2(5) . . ?
N3 C4 C9 124.4(5) . . ?
C6 C5 C4 121.6(5) . . ?
C5 C6 C7 122.1(5) . . ?
O2 C7 C6 120.1(5) . . ?
O2 C7 C8 121.5(5) . . ?
C6 C7 C8 118.4(5) . . ?
C7 C8 C9 120.1(5) . . ?
C7 C8 C10 120.8(5) . . ?
C9 C8 C10 119.1(5) . . ?
C8 C9 C4 120.7(5) . . ?
O3 C10 O4 122.5(5) . . ?
O3 C10 C8 122.4(5) . . ?
O4 C10 C8 115.0(5) . . ?
O5 C12 N11 122.5(5) . . ?
O5 C12 N13 120.8(5) . . ?
N11 C12 N13 116.7(5) . . ?
C12 N13 C14 129.0(4) . . ?
C19 C14 C15 118.3(5) . . ?
C19 C14 N13 123.5(5) . . ?
C15 C14 N13 118.1(5) . . ?
C16 C15 C14 122.0(5) . . ?
C15 C16 C17 120.2(5) . . ?
O6 C17 C16 118.4(5) . . ?
O6 C17 C18 122.3(5) . . ?
C16 C17 C18 119.3(5) . . ?
C17 C18 C19 119.6(5) . . ?
C17 C18 C20 120.8(5) . . ?
C19 C18 C20 119.6(5) . . ?
C14 C19 C18 120.6(5) . . ?
O7 C20 O8 123.2(5) . . ?
O7 C20 C18 122.2(5) . . ?
O8 C20 C18 114.6(5) . . ?
O9 C22 N23 123.7(5) . . ?
O9 C22 N21 121.1(5) . . ?
N23 C22 N21 115.2(5) . . ?
C22 N23 C24 128.0(5) . . ?
C29 C24 C25 118.2(6) . . ?
C29 C24 N23 123.7(5) . . ?
C25 C24 N23 118.0(5) . . ?
C26 C25 C24 122.6(6) . . ?
C25 C26 C27 120.1(6) . . ?
O10 C27 C26 118.5(5) . . ?
O10 C27 C28 122.7(6) . . ?
C26 C27 C28 118.8(6) . . ?
C27 C28 C29 119.3(6) . . ?
C27 C28 C30 120.7(5) . . ?
C29 C28 C30 120.0(5) . . ?
C24 C29 C28 121.0(5) . . ?
O11 C30 O12 124.2(6) . . ?
O11 C30 C28 121.4(5) . . ?
O12 C30 C28 114.4(5) . . ?
O13 C32 N31 121.3(5) . . ?
O13 C32 N33 123.1(5) . . ?
N31 C32 N33 115.4(5) . . ?
C32 N33 C34 127.5(5) . . ?
C39 C34 C35 118.3(5) . . ?
C39 C34 N33 124.8(5) . . ?
C35 C34 N33 116.9(5) . . ?
C36 C35 C34 121.4(5) . . ?
C37 C36 C35 121.3(6) . . ?
C36 C37 O14 118.4(5) . . ?
C36 C37 C38 119.3(5) . . ?
O14 C37 C38 122.4(5) . . ?
C37 C38 C39 119.4(5) . . ?
C37 C38 C40 120.1(5) . . ?
C39 C38 C40 120.4(5) . . ?
C34 C39 C38 120.3(5) . . ?
O15 C40 O16 122.7(5) . . ?
O15 C40 C38 122.3(5) . . ?
O16 C40 C38 115.1(5) . . ?
O17 C42 N41 120.8(5) . . ?
O17 C42 N43 122.5(5) . . ?
N41 C42 N43 116.8(5) . . ?
C42 N43 C44 129.3(5) . . ?
C49 C44 C45 117.9(5) . . ?
C49 C44 N43 125.1(5) . . ?
C45 C44 N43 117.0(5) . . ?
C44 C45 C46 121.9(6) . . ?
C47 C46 C45 120.4(5) . . ?
O18 C47 C46 118.3(5) . . ?
O18 C47 C48 122.7(5) . . ?
C46 C47 C48 119.0(5) . . ?
C49 C48 C47 119.1(5) . . ?
C49 C48 C50 120.8(5) . . ?
C47 C48 C50 120.1(5) . . ?
C44 C49 C48 121.6(5) . . ?
O19 C50 O20 122.5(5) . . ?
O19 C50 C48 123.5(5) . . ?
O20 C50 C48 114.0(5) . . ?
O21 C52 N51 123.1(5) . . ?
O21 C52 N53 121.7(5) . . ?
N51 C52 N53 115.2(5) . . ?
C52 N53 C54 128.3(5) . . ?
C59 C54 C55 118.0(5) . . ?
C59 C54 N53 124.3(4) . . ?
C55 C54 N53 117.7(5) . . ?
C56 C55 C54 122.0(5) . . ?
C55 C56 C57 120.9(5) . . ?
O22 C57 C56 118.6(5) . . ?
O22 C57 C58 123.3(5) . . ?
C56 C57 C58 118.1(5) . . ?
C59 C58 C57 120.2(5) . . ?
C59 C58 C60 120.5(5) . . ?
C57 C58 C60 119.3(5) . . ?
C54 C59 C58 120.6(5) . . ?
O23 C60 O24 122.7(5) . . ?
O23 C60 C58 122.5(5) . . ?
O24 C60 C58 114.8(5) . . ?
O25 C62 C63 122.4(5) . . ?
O25 C62 C61 120.5(6) . . ?
C63 C62 C61 117.2(5) . . ?
O26 C65 C66 120.9(6) . . ?
O26 C65 C64 120.2(6) . . ?
C66 C65 C64 118.9(6) . . ?
O27 C68 C69 119.2(7) . . ?
O27 C68 C67 121.9(6) . . ?
C69 C68 C67 118.9(6) . . ?
O28 C71 C72 120.6(7) . . ?
O28 C71 C70 123.0(7) . . ?
C72 C71 C70 116.4(7) . . ?
O29 C74 C73 120.3(6) . . ?
O29 C74 C75 122.4(5) . . ?
C73 C74 C75 117.3(6) . . ?
O30 C77 C78 121.8(5) . . ?
O30 C77 C76 119.4(5) . . ?
C78 C77 C76 118.7(6) . . ?

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 H1A O11 0.88 2.14 2.987(6) 161.0 .
N1 H1B O6 0.88 2.32 3.018(6) 136.3 2_655
N1 H1B O29 0.88 2.58 3.309(6) 140.7 .
O2 H2O O3 0.84 1.87 2.604(5) 145.3 .
N3 H3 O29 0.88 2.00 2.877(6) 173.0 .
O4 H4O O5 0.84 1.70 2.523(5) 164.2 .
O6 H6O O7 0.84 1.87 2.604(5) 145.2 .
O8 H8O O9 0.84 1.73 2.540(5) 161.9 .
O10 H10O O11 0.84 1.88 2.614(6) 145.2 .
N11 H11A O3 0.88 2.07 2.926(6) 165.7 .
N11 H11B O26 0.88 2.10 2.896(6) 150.0 3_656
O12 H12O O1 0.84 1.71 2.525(5) 162.3 .
N13 H13 O26 0.88 2.10 2.915(6) 154.3 3_656
O14 H14O O15 0.84 1.86 2.600(5) 145.3 .
O16 H16O O21 0.84 1.71 2.537(5) 166.1 .
O18 H18O O19 0.84 1.89 2.623(5) 145.0 .
O20 H20O O13 0.84 1.70 2.515(6) 163.7 .
N21 H21A O7 0.88 2.10 2.951(6) 161.8 .
N21 H21B O27 0.88 2.09 2.904(6) 153.7 .
O22 H22O O23 0.84 1.87 2.599(5) 144.8 .
N23 H23 O27 0.88 2.18 3.002(6) 154.7 .
O24 H24O O17 0.84 1.69 2.507(5) 163.0 .
N31 H31A O19 0.88 2.15 2.992(6) 159.6 .
N31 H31B O22 0.88 2.54 3.107(6) 122.9 2_656
N31 H31B O25 0.88 2.58 3.313(7) 141.0 4_666
N33 H33 O25 0.88 2.03 2.899(6) 168.9 4_666
N41 H41A O23 0.88 2.07 2.933(6) 166.4 .
N41 H41B O28 0.88 2.14 2.921(6) 147.4 .
N43 H43 O28 0.88 2.05 2.878(6) 156.1 .
N51 H51A O15 0.88 2.15 2.993(6) 160.0 .
N51 H51B O30 0.88 2.17 2.962(6) 149.4 .
N53 H53 O30 0.88 2.05 2.883(6) 157.8 .

_refine_diff_density_max         0.597
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.078



####################################################################### 
# 
# 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_NBZSQZ
_database_code_depnum_ccdc_archive 'CCDC 1495379'
_audit_update_record             
;
2016-07-22 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_CHEMW03_NBZSQZ              
;
PROBLEM: ALERT: The ratio of given/expected molecular weight as
RESPONSE: Squeeze used
;
# Added during the CSD deposition process: Friday 22 July 2016 10:00 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12.20 H11.50 N2.70 O5.40'
_chemical_formula_weight         282.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0010 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           114
_space_group_name_H-M_alt        'P -4 21 c'
_space_group_name_Hall           'P -4 2n'

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

_cell_length_a                   17.707(3)
_cell_length_b                   17.707(3)
_cell_length_c                   7.3732(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2311.8(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2853
_cell_measurement_theta_min      1.58
_cell_measurement_theta_max      27.31

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_F_000             1174
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.001
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   1.000
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'Diamond I19'
_diffrn_measurement_device_type  'Diamond I19'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22865
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         1.576
_diffrn_reflns_theta_max         27.310
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2853
_reflns_number_gt                2613
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.997

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.1042P)²+3.3608P] 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 1007 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2853
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0749
_refine_ls_wR_factor_ref         0.2027
_refine_ls_wR_factor_gt          0.1999
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.24353(18) 0.62660(18) 0.8034(5) 0.0332(8) Uani 1 1 d . . . . .
N1 N 0.1575(2) 0.6182(2) 1.0283(5) 0.0335(9) Uani 1 1 d . . . . .
H1A H 0.1405 0.5760 0.9877 0.040 Uiso 1 1 calc R U . . .
H1B H 0.1382 0.6379 1.1242 0.040 Uiso 1 1 calc R U . . .
C1 C 0.2139(3) 0.6531(2) 0.9424(6) 0.0271(9) Uani 1 1 d . . . . .
O2 O 0.48014(16) 0.88378(17) 0.7337(5) 0.0324(8) Uani 1 1 d . . . . .
H2 H 0.4657 0.9208 0.6766 0.039 Uiso 1 1 calc R U . . .
N2 N 0.2368(2) 0.7201(2) 1.0113(5) 0.0297(8) Uani 1 1 d . . . . .
H2A H 0.2132 0.7380 1.1037 0.036 Uiso 1 1 calc R U . . .
C2 C 0.2981(2) 0.7627(2) 0.9382(6) 0.0241(8) Uani 1 1 d . . . . .
O3 O 0.39075(19) 0.99898(16) 0.7188(5) 0.0301(7) Uani 1 1 d . . . . .
C3 C 0.2880(2) 0.8366(2) 0.8976(5) 0.0239(8) Uani 1 1 d . . . . .
H3 H 0.2409 0.8587 0.9141 0.029 Uiso 1 1 calc R U . . .
O4 O 0.27092(18) 0.98703(18) 0.8050(5) 0.0314(7) Uani 1 1 d . . . . .
C4 C 0.3490(2) 0.8803(2) 0.8301(5) 0.0216(8) Uani 1 1 d . . . . .
C5 C 0.4191(2) 0.8457(2) 0.8002(6) 0.0232(8) Uani 1 1 d . . . . .
C6 C 0.4284(2) 0.7700(2) 0.8421(7) 0.0301(10) Uani 1 1 d . . . . .
H6 H 0.4748 0.7468 0.8227 0.036 Uiso 1 1 calc R U . . .
C7 C 0.3684(2) 0.7284(2) 0.9135(6) 0.0278(9) Uani 1 1 d . . . . .
H7 H 0.3752 0.6780 0.9445 0.033 Uiso 1 1 calc R U . . .
C8 C 0.3391(2) 0.9604(2) 0.7802(6) 0.0234(8) Uani 1 1 d . . . . .
H4 H 0.2540 1.0329 0.7773 0.11(3) Uiso 1 1 d R . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.243(6) . ?
N1 C1 1.334(5) . ?
C1 N2 1.354(5) . ?
O2 C5 1.365(5) . ?
N2 C2 1.427(5) . ?
C2 C3 1.354(6) . ?
C2 C7 1.397(6) . ?
O3 C8 1.227(5) . ?
C3 C4 1.419(5) . ?
O4 C8 1.309(5) . ?
C4 C5 1.403(5) . ?
C4 C8 1.476(5) . ?
C5 C6 1.385(6) . ?
C6 C7 1.396(6) . ?

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
O1 C1 N1 122.2(4) . . ?
O1 C1 N2 120.9(4) . . ?
N1 C1 N2 116.9(4) . . ?
C1 N2 C2 123.3(4) . . ?
C3 C2 C7 120.6(4) . . ?
C3 C2 N2 119.5(4) . . ?
C7 C2 N2 119.9(4) . . ?
C2 C3 C4 120.3(4) . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 C8 119.1(3) . . ?
C3 C4 C8 121.5(4) . . ?
O2 C5 C6 117.7(4) . . ?
O2 C5 C4 122.7(3) . . ?
C6 C5 C4 119.6(4) . . ?
C5 C6 C7 120.3(4) . . ?
C6 C7 C2 119.9(4) . . ?
O3 C8 O4 122.6(4) . . ?
O3 C8 C4 122.6(4) . . ?
O4 C8 C4 114.9(3) . . ?

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 H1A O3 0.86 2.12 2.916(5) 154.4 6_546
N1 H1B O1 0.86 2.30 3.056(5) 147.0 8_455
O2 H2 O3 0.82 1.94 2.584(4) 134.5 .
N2 H2A O1 0.86 2.13 2.935(5) 156.3 8_455
O4 H4 O1 0.89 1.76 2.610(4) 158.1 6_556

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.081

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.023 365 179 ' '
2 0.500 0.500 -0.045 365 179 ' '
_platon_squeeze_details          
;
From PLaton electron count of 358 per cell there should be 5.6 nitrobenzene
molecules per unit cell.
;



####################################################################### 
# 
# 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_4Picoline
_database_code_depnum_ccdc_archive 'CCDC 1495380'
_audit_update_record             
;
2016-07-22 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 N4 O4'
_chemical_formula_weight         382.42

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   4.5668(4)
_cell_length_b                   20.5310(16)
_cell_length_c                   20.9009(16)
_cell_angle_alpha                76.149(2)
_cell_angle_beta                 88.228(3)
_cell_angle_gamma                88.156(3)
_cell_volume                     1901.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    121
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      22.25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          1.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.731
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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  'Bruker D8 Venture'
_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            21149
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_sigmaI/netI    0.0886
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         24.80
_reflns_number_total             6528
_reflns_number_gt                4312
_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)+(0.0504P)²+2.0498P] 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         6528
_refine_ls_number_parameters     509
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0653
_refine_ls_wR_factor_ref         0.1557
_refine_ls_wR_factor_gt          0.1367
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_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
O1 O 0.9252(4) 0.37738(13) 0.40039(10) 0.0373(6) Uani 1 1 d . . .
N1 N 1.3448(6) 0.38477(16) 0.45189(13) 0.0395(8) Uani 1 1 d . . .
H1A H 1.2506 0.3883 0.4883 0.047 Uiso 1 1 calc R . .
H1B H 1.5375 0.3854 0.4497 0.047 Uiso 1 1 calc R . .
O2 O 0.8644(5) 0.31925(10) 0.12499(10) 0.0268(5) Uani 1 1 d . . .
H2O H 0.7396 0.3491 0.1087 0.032 Uiso 1 1 calc R . .
C2 C 1.1951(7) 0.37847(18) 0.39974(15) 0.0309(8) Uani 1 1 d . . .
O3 O 0.5738(4) 0.42941(10) 0.11053(9) 0.0219(5) Uani 1 1 d . . .
N3 N 1.3590(5) 0.37251(15) 0.34615(12) 0.0298(7) Uani 1 1 d . . .
H3 H 1.5503 0.3762 0.3468 0.036 Uiso 1 1 calc R . .
O4 O 0.6117(4) 0.49186(10) 0.18352(10) 0.0229(5) Uani 1 1 d . . .
H4O H 0.4866 0.5157 0.1592 0.027 Uiso 1 1 calc R . .
C4 C 1.2319(6) 0.36052(16) 0.28890(14) 0.0221(7) Uani 1 1 d . . .
O5 O -0.0053(5) 0.00223(11) 0.32855(13) 0.0379(6) Uani 1 1 d . . .
C5 C 1.3179(6) 0.30360(16) 0.26693(15) 0.0250(7) Uani 1 1 d . . .
H5 H 1.4618 0.2733 0.2901 0.030 Uiso 1 1 calc R . .
O6 O 0.1310(6) -0.23502(12) 0.18171(14) 0.0496(7) Uani 1 1 d . . .
H6O H 0.2228 -0.2315 0.1457 0.059 Uiso 1 1 calc R . .
C6 C 1.1954(6) 0.29101(15) 0.21182(15) 0.0241(7) Uani 1 1 d . . .
H6 H 1.2570 0.2524 0.1969 0.029 Uiso 1 1 calc R . .
O7 O 0.4857(6) -0.18542(12) 0.08736(13) 0.0465(7) Uani 1 1 d . . .
C7 C 0.9831(6) 0.33434(15) 0.17814(14) 0.0200(7) Uani 1 1 d . . .
O8 O 0.6759(6) -0.08558(12) 0.08254(13) 0.0467(7) Uani 1 1 d . . .
H8O H 0.7383 -0.0907 0.0458 0.056 Uiso 1 1 calc R . .
C8 C 0.8995(6) 0.39244(14) 0.19850(13) 0.0167(6) Uani 1 1 d . . .
C9 C 1.0275(6) 0.40472(15) 0.25406(14) 0.0206(7) Uani 1 1 d . . .
H9 H 0.9728 0.4442 0.2681 0.025 Uiso 1 1 calc R . .
C10 C 0.6802(6) 0.44012(14) 0.16122(14) 0.0180(7) Uani 1 1 d . . .
N11 N 0.3956(6) 0.04980(13) 0.35534(14) 0.0336(7) Uani 1 1 d . . .
H11A H 0.2891 0.0772 0.3737 0.040 Uiso 1 1 calc R . .
H11B H 0.5880 0.0514 0.3547 0.040 Uiso 1 1 calc R . .
C12 C 0.2652(7) 0.00584(15) 0.32849(17) 0.0268(8) Uani 1 1 d . . .
N13 N 0.4446(5) -0.03372(12) 0.30054(13) 0.0268(6) Uani 1 1 d . . .
H13 H 0.6345 -0.0284 0.3020 0.032 Uiso 1 1 calc R . .
C14 C 0.3513(6) -0.08320(15) 0.26905(17) 0.0250(8) Uani 1 1 d . . .
C15 C 0.1498(7) -0.13121(15) 0.29892(18) 0.0305(8) Uani 1 1 d . . .
H15 H 0.0634 -0.1298 0.3405 0.037 Uiso 1 1 calc R . .
C16 C 0.0750(7) -0.18055(16) 0.26870(19) 0.0349(9) Uani 1 1 d . . .
H16 H -0.0661 -0.2124 0.2892 0.042 Uiso 1 1 calc R . .
C17 C 0.2026(7) -0.18434(16) 0.2088(2) 0.0356(9) Uani 1 1 d . . .
C18 C 0.4010(7) -0.13536(16) 0.17763(17) 0.0303(8) Uani 1 1 d . . .
C19 C 0.4722(7) -0.08546(15) 0.20871(17) 0.0259(8) Uani 1 1 d . . .
H19 H 0.6071 -0.0523 0.1878 0.031 Uiso 1 1 calc R . .
C20 C 0.5285(8) -0.13638(17) 0.11158(19) 0.0365(9) Uani 1 1 d . . .
C21 C -0.2218(8) 0.13601(18) 0.20792(19) 0.0439(10) Uani 1 1 d . . .
H21A H -0.4160 0.1165 0.2173 0.066 Uiso 1 1 calc R . .
H21B H -0.2386 0.1846 0.2032 0.066 Uiso 1 1 calc R . .
H21C H -0.0917 0.1161 0.2443 0.066 Uiso 1 1 calc R . .
C22 C -0.0992(7) 0.12209(15) 0.14585(18) 0.0300(8) Uani 1 1 d . . .
C23 C -0.1260(8) 0.16865(17) 0.08599(19) 0.0392(9) Uani 1 1 d . . .
H23 H -0.2229 0.2106 0.0843 0.047 Uiso 1 1 calc R . .
C24 C -0.0144(8) 0.15451(16) 0.02974(19) 0.0382(9) Uani 1 1 d . . .
H24 H -0.0356 0.1872 -0.0107 0.046 Uiso 1 1 calc R . .
N25 N 0.1240(6) 0.09636(13) 0.02922(15) 0.0373(7) Uani 1 1 d . . .
C26 C 0.1538(9) 0.05100(17) 0.0863(2) 0.0453(10) Uani 1 1 d . . .
H26 H 0.2530 0.0096 0.0865 0.054 Uiso 1 1 calc R . .
C27 C 0.0465(8) 0.06213(16) 0.14443(19) 0.0386(9) Uani 1 1 d . . .
H27 H 0.0717 0.0287 0.1842 0.046 Uiso 1 1 calc R . .
C28 C 0.3582(9) 0.1934(4) 0.5521(2) 0.125(3) Uani 1 1 d . . .
H28A H 0.3389 0.2425 0.5402 0.187 Uiso 1 1 calc R . .
H28B H 0.4335 0.1785 0.5967 0.187 Uiso 1 1 calc R . .
H28C H 0.1660 0.1741 0.5504 0.187 Uiso 1 1 calc R . .
C29 C 0.5680(8) 0.1706(3) 0.50398(17) 0.0504(12) Uani 1 1 d . . .
C30 C 0.7018(7) 0.21582(18) 0.45417(17) 0.0329(8) Uani 1 1 d . . .
H30 H 0.6632 0.2625 0.4489 0.040 Uiso 1 1 calc R . .
C31 C 0.8914(7) 0.19360(17) 0.41198(16) 0.0307(8) Uani 1 1 d . . .
H31 H 0.9809 0.2264 0.3777 0.037 Uiso 1 1 calc R . .
N32 N 0.9597(7) 0.13038(17) 0.41506(17) 0.0447(8) Uani 1 1 d . . .
C33 C 0.8324(12) 0.0872(2) 0.4626(3) 0.0669(16) Uani 1 1 d . . .
H33 H 0.8787 0.0410 0.4662 0.080 Uiso 1 1 calc R . .
C34 C 0.6360(12) 0.1029(3) 0.5080(2) 0.078(2) Uani 1 1 d . . .
H34 H 0.5488 0.0688 0.5413 0.094 Uiso 1 1 calc R . .
C35 C -0.4024(7) 0.69686(15) -0.00419(15) 0.0237(7) Uani 1 1 d . . .
H35A H -0.4447 0.7363 0.0135 0.035 Uiso 1 1 calc R . .
H35B H -0.5841 0.6731 -0.0054 0.035 Uiso 1 1 calc R . .
H35C H -0.3186 0.7111 -0.0489 0.035 Uiso 1 1 calc R . .
C36 C -0.1872(6) 0.65089(14) 0.03906(14) 0.0169(6) Uani 1 1 d . . .
C37 C -0.0717(6) 0.59413(14) 0.02144(15) 0.0194(7) Uani 1 1 d . . .
H37 H -0.1333 0.5829 -0.0175 0.023 Uiso 1 1 calc R . .
C38 C 0.1314(7) 0.55445(14) 0.06047(15) 0.0213(7) Uani 1 1 d . . .
H38 H 0.2112 0.5162 0.0474 0.026 Uiso 1 1 calc R . .
N39 N 0.2219(5) 0.56728(12) 0.11616(12) 0.0184(6) Uani 1 1 d . . .
C40 C 0.1073(6) 0.62113(14) 0.13447(14) 0.0192(7) Uani 1 1 d . . .
H40 H 0.1681 0.6303 0.1744 0.023 Uiso 1 1 calc R . .
C41 C -0.0954(6) 0.66355(14) 0.09728(15) 0.0202(7) Uani 1 1 d . . .
H41 H -0.1722 0.7014 0.1115 0.024 Uiso 1 1 calc R . .
C42 C 1.6584(8) 0.6274(2) 0.27162(17) 0.0469(10) Uani 1 1 d . . .
H42A H 1.6755 0.5862 0.2557 0.070 Uiso 1 1 calc R . .
H42B H 1.8513 0.6385 0.2847 0.070 Uiso 1 1 calc R . .
H42C H 1.5844 0.6643 0.2364 0.070 Uiso 1 1 calc R . .
C43 C 1.4501(7) 0.6170(2) 0.32990(16) 0.0369(9) Uani 1 1 d . . .
C44 C 1.3190(9) 0.5566(2) 0.35556(19) 0.0483(10) Uani 1 1 d . . .
H44 H 1.3630 0.5194 0.3368 0.058 Uiso 1 1 calc R . .
C45 C 1.1244(9) 0.5496(2) 0.4083(2) 0.0538(11) Uani 1 1 d . . .
H45 H 1.0357 0.5074 0.4245 0.065 Uiso 1 1 calc R . .
N46 N 1.0542(7) 0.5988(2) 0.43764(15) 0.0508(9) Uani 1 1 d . . .
C47 C 1.1839(8) 0.6565(3) 0.4133(2) 0.0496(11) Uani 1 1 d . . .
H47 H 1.1394 0.6925 0.4336 0.060 Uiso 1 1 calc R . .
C48 C 1.3783(8) 0.6679(2) 0.36062(18) 0.0420(10) Uani 1 1 d . . .
H48 H 1.4629 0.7107 0.3454 0.050 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.233(4) . ?
N1 C2 1.339(4) . ?
O2 C7 1.355(3) . ?
C2 N3 1.356(4) . ?
O3 C10 1.248(3) . ?
N3 C4 1.422(4) . ?
O4 C10 1.285(3) . ?
C4 C9 1.377(4) . ?
C4 C5 1.395(4) . ?
O5 C12 1.240(4) . ?
C5 C6 1.377(4) . ?
O6 C17 1.352(4) . ?
C6 C7 1.384(4) . ?
O7 C20 1.253(4) . ?
C7 C8 1.398(4) . ?
O8 C20 1.275(4) . ?
C8 C9 1.395(4) . ?
C8 C10 1.479(4) . ?
N11 C12 1.335(4) . ?
C12 N13 1.352(4) . ?
N13 C14 1.418(4) . ?
C14 C19 1.371(5) . ?
C14 C15 1.391(5) . ?
C15 C16 1.373(4) . ?
C16 C17 1.382(5) . ?
C17 C18 1.402(5) . ?
C18 C19 1.389(4) . ?
C18 C20 1.486(5) . ?
C21 C22 1.483(5) . ?
C22 C23 1.387(5) . ?
C22 C27 1.387(5) . ?
C23 C24 1.358(5) . ?
C24 N25 1.335(4) . ?
N25 C26 1.334(5) . ?
C26 C27 1.362(5) . ?
C28 C29 1.511(6) . ?
C29 C30 1.361(5) . ?
C29 C34 1.397(7) . ?
C30 C31 1.362(5) . ?
C31 N32 1.312(4) . ?
N32 C33 1.299(6) . ?
C33 C34 1.373(7) . ?
C35 C36 1.504(4) . ?
C36 C41 1.383(4) . ?
C36 C37 1.388(4) . ?
C37 C38 1.367(4) . ?
C38 N39 1.334(4) . ?
N39 C40 1.340(4) . ?
C40 C41 1.374(4) . ?
C42 C43 1.500(5) . ?
C43 C48 1.379(5) . ?
C43 C44 1.376(5) . ?
C44 C45 1.378(5) . ?
C45 N46 1.326(5) . ?
N46 C47 1.324(5) . ?
C47 C48 1.372(5) . ?

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
O1 C2 N1 122.4(3) . . ?
O1 C2 N3 121.9(3) . . ?
N1 C2 N3 115.8(3) . . ?
C2 N3 C4 122.1(3) . . ?
C9 C4 C5 119.2(3) . . ?
C9 C4 N3 121.1(3) . . ?
C5 C4 N3 119.7(3) . . ?
C6 C5 C4 120.4(3) . . ?
C5 C6 C7 120.2(3) . . ?
O2 C7 C6 118.2(3) . . ?
O2 C7 C8 121.7(3) . . ?
C6 C7 C8 120.1(3) . . ?
C9 C8 C7 118.9(3) . . ?
C9 C8 C10 120.9(3) . . ?
C7 C8 C10 120.2(3) . . ?
C4 C9 C8 121.1(3) . . ?
O3 C10 O4 123.3(3) . . ?
O3 C10 C8 120.1(3) . . ?
O4 C10 C8 116.6(3) . . ?
O5 C12 N11 121.7(3) . . ?
O5 C12 N13 122.1(3) . . ?
N11 C12 N13 116.2(3) . . ?
C12 N13 C14 125.2(3) . . ?
C19 C14 C15 119.1(3) . . ?
C19 C14 N13 119.0(3) . . ?
C15 C14 N13 121.8(3) . . ?
C16 C15 C14 120.5(3) . . ?
C15 C16 C17 120.7(3) . . ?
O6 C17 C16 119.0(3) . . ?
O6 C17 C18 121.7(3) . . ?
C16 C17 C18 119.2(3) . . ?
C19 C18 C17 119.2(3) . . ?
C19 C18 C20 120.7(3) . . ?
C17 C18 C20 120.1(3) . . ?
C14 C19 C18 121.2(3) . . ?
O7 C20 O8 123.8(4) . . ?
O7 C20 C18 119.7(3) . . ?
O8 C20 C18 116.5(3) . . ?
C23 C22 C27 116.5(3) . . ?
C23 C22 C21 121.4(3) . . ?
C27 C22 C21 122.1(3) . . ?
C24 C23 C22 120.3(3) . . ?
N25 C24 C23 122.3(3) . . ?
C26 N25 C24 118.3(3) . . ?
N25 C26 C27 122.2(3) . . ?
C26 C27 C22 120.3(3) . . ?
C30 C29 C34 116.5(4) . . ?
C30 C29 C28 121.1(5) . . ?
C34 C29 C28 122.4(5) . . ?
C29 C30 C31 119.5(4) . . ?
N32 C31 C30 125.0(3) . . ?
C33 N32 C31 115.6(4) . . ?
N32 C33 C34 125.2(4) . . ?
C33 C34 C29 118.2(4) . . ?
C41 C36 C37 117.6(3) . . ?
C41 C36 C35 121.7(3) . . ?
C37 C36 C35 120.8(3) . . ?
C38 C37 C36 119.6(3) . . ?
N39 C38 C37 122.7(3) . . ?
C38 N39 C40 118.4(3) . . ?
N39 C40 C41 122.1(3) . . ?
C40 C41 C36 119.7(3) . . ?
C48 C43 C44 116.2(3) . . ?
C48 C43 C42 121.5(4) . . ?
C44 C43 C42 122.3(4) . . ?
C45 C44 C43 120.3(4) . . ?
N46 C45 C44 123.4(4) . . ?
C45 N46 C47 116.0(3) . . ?
N46 C47 C48 124.4(4) . . ?
C47 C48 C43 119.6(4) . . ?

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 H1A N46 0.88 2.11 2.973(4) 167.6 2_766
N1 H1B O1 0.88 2.04 2.843(3) 150.6 1_655
O2 H2O O3 0.84 1.80 2.544(3) 146.6 .
N3 H3 O1 0.88 2.08 2.868(3) 149.1 1_655
O4 H4O N39 0.84 1.71 2.546(3) 174.4 .
O6 H6O O7 0.84 1.80 2.549(4) 147.0 .
O8 H8O N25 0.84 1.70 2.539(4) 176.3 2_655
N11 H11A N32 0.88 2.11 2.980(4) 167.9 1_455
N11 H11B O5 0.88 2.20 2.957(3) 143.8 1_655
N13 H13 O5 0.88 1.92 2.760(3) 158.2 1_655

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        24.80
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_Water
_database_code_depnum_ccdc_archive 'CCDC 1495381'
_audit_update_record             
;
2016-07-22 deposited with the CCDC.
2016-09-01 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         ?
_chemical_formula_sum            'C8 H10 N2 O5'
_chemical_formula_weight         214.18

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

_cell_length_a                   4.5426(19)
_cell_length_b                   10.729(5)
_cell_length_c                   18.692(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     911.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    213
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      32.35

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.184
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6103
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9640
_diffrn_reflns_av_unetI/netI     0.0894
_diffrn_reflns_av_R_equivalents  0.1211
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.189
_diffrn_reflns_theta_max         24.830
_diffrn_reflns_theta_full        24.830
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1573
_reflns_number_gt                1138
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.635
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.992

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    X-Seed
_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)+(0.0642P)²] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.013(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 349 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.6(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1573
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1122
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
O3 O 0.1169(8) 0.5308(3) 0.0415(2) 0.0250(10) Uani 1 1 d . . . . .
O2 O 0.4383(9) 0.7317(3) 0.05152(19) 0.0264(10) Uani 1 1 d . . . . .
O1 O 0.4155(7) 0.5571(3) 0.37014(18) 0.0209(10) Uani 1 1 d . . . . .
O4 O 0.1227(9) 0.3900(4) 0.1287(2) 0.0253(10) Uani 1 1 d . . . . .
N3 N 0.8470(12) 0.5469(5) 0.3108(3) 0.0226(12) Uani 1 1 d . . . . .
H3 H 1.002(14) 0.550(5) 0.317(3) 0.010(17) Uiso 1 1 d . . . . .
C8 C 0.4264(11) 0.5671(4) 0.1409(3) 0.0167(12) Uani 1 1 d . . . . .
C9 C 0.5338(11) 0.5238(5) 0.2064(3) 0.0184(13) Uani 1 1 d . . . . .
H9 H 0.4663 0.4463 0.2246 0.022 Uiso 1 1 calc R U . . .
N1 N 0.8288(12) 0.5151(5) 0.4317(3) 0.0226(13) Uani 1 1 d . . . . .
H1A H 0.729(14) 0.505(4) 0.470(3) 0.016(15) Uiso 1 1 d . . . . .
H1B H 0.994(15) 0.504(5) 0.434(3) 0.03(2) Uiso 1 1 d . . . . .
C7 C 0.5295(13) 0.6809(5) 0.1140(3) 0.0202(14) Uani 1 1 d . . . . .
C4 C 0.7360(12) 0.5919(5) 0.2447(3) 0.0189(13) Uani 1 1 d . . . . .
C2 C 0.6887(11) 0.5405(5) 0.3710(3) 0.0166(12) Uani 1 1 d . . . . .
C5 C 0.8389(12) 0.7041(5) 0.2173(3) 0.0213(14) Uani 1 1 d . . . . .
H5 H 0.9794 0.7512 0.2435 0.026 Uiso 1 1 calc R U . . .
C10 C 0.2097(12) 0.4957(5) 0.0997(3) 0.0189(13) Uani 1 1 d . . . . .
C6 C 0.7378(13) 0.7469(5) 0.1527(3) 0.0253(14) Uani 1 1 d . . . . .
H6 H 0.8120 0.8231 0.1341 0.030 Uiso 1 1 calc R U . . .
O1S O -0.2394(9) 0.2566(4) 0.0472(2) 0.0257(10) Uani 1 1 d . . . . .
H1S H -0.39(2) 0.281(7) 0.021(4) 0.09(3) Uiso 1 1 d . . . . .
H2S H -0.28(3) 0.190(9) 0.073(5) 0.12(4) Uiso 1 1 d . . . . .
H2 H 0.254(18) 0.679(6) 0.031(3) 0.06(2) Uiso 1 1 d . . . . .
H4 H 0.03(3) 0.343(10) 0.105(5) 0.14(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C10 1.226(6) . ?
O2 C7 1.353(6) . ?
O1 C2 1.254(6) . ?
O4 C10 1.318(6) . ?
N3 C2 1.337(7) . ?
N3 C4 1.420(7) . ?
C8 C9 1.396(7) . ?
C8 C7 1.402(7) . ?
C8 C10 1.466(7) . ?
C9 C4 1.375(7) . ?
N1 C2 1.329(7) . ?
C7 C6 1.386(8) . ?
C4 C5 1.388(7) . ?
C5 C6 1.372(7) . ?

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 N3 C4 124.0(5) . . ?
C9 C8 C7 119.2(5) . . ?
C9 C8 C10 121.4(5) . . ?
C7 C8 C10 119.3(5) . . ?
C4 C9 C8 120.8(5) . . ?
O2 C7 C6 117.0(5) . . ?
O2 C7 C8 124.0(5) . . ?
C6 C7 C8 119.0(5) . . ?
C9 C4 C5 119.6(5) . . ?
C9 C4 N3 120.7(5) . . ?
C5 C4 N3 119.7(5) . . ?
O1 C2 N1 121.0(5) . . ?
O1 C2 N3 120.9(5) . . ?
N1 C2 N3 118.1(5) . . ?
C6 C5 C4 120.1(6) . . ?
O3 C10 O4 121.8(5) . . ?
O3 C10 C8 122.5(5) . . ?
O4 C10 C8 115.7(5) . . ?
C5 C6 C7 121.1(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
N3 H3 O1 0.72(6) 2.12(6) 2.812(6) 162(5) 1_655
N1 H1A O3 0.85(6) 2.10(6) 2.925(7) 163(5) 2_565
N1 H1B O1 0.76(7) 2.33(6) 2.938(6) 138(6) 1_655
O1S H1S O1S 0.89(9) 2.07(9) 2.881(5) 151(7) 3_455
O1S H2S O1 0.88(10) 1.89(10) 2.757(6) 171(11) 4_545
O2 H2 O3 1.08(8) 1.72(7) 2.610(5) 136(5) .
O2 H2 O2 1.08(8) 2.31(7) 3.004(5) 120(4) 3_465
O4 H4 O1S 0.81(11) 1.86(12) 2.660(6) 170(12) .

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.064



