# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_16kaw29a
_database_code_depnum_ccdc_archive 'CCDC 1832191'
_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-06-18 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 H16 N4 O7'
_chemical_formula_weight         280.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.0233(5)
_cell_length_b                   7.9864(6)
_cell_length_c                   9.3673(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.686(2)
_cell_angle_gamma                90
_cell_volume                     597.28(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7643
_cell_measurement_theta_min      4.74
_cell_measurement_theta_max      68.32

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.424
_exptl_crystal_size_mid          0.279
_exptl_crystal_size_min          0.114
_exptl_absorpt_coefficient_mu    1.189
_shelx_estimated_absorpt_T_min   0.633
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
_exptl_absorpt_special_details   ?


_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8907
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.744
_diffrn_reflns_theta_max         68.209
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.931
_reflns_number_total             2042
_reflns_number_gt                2022
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_max     0.852
_reflns_Friedel_fraction_full    0.854

_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       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms. Those H atoms attached to nitrogen or oxygen were
 located in Fourier diff maps and assigned Uiso = 1.2xUeqiv with 
 N-H and O-H bond distances restrained to 0.85(2) angstroms.
;


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0509P)²+0.1305P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 841 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(7)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2042
_refine_ls_number_parameters     225
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_ref         0.0756
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
O1A O 0.56339(17) 0.5468(2) 1.11001(15) 0.0128(4) Uani 1 1 d . . . . .
O2A O 0.26624(19) 0.3341(2) 0.86125(17) 0.0135(4) Uani 1 1 d D . . . .
H5A H 0.310(4) 0.243(3) 0.872(3) 0.016 Uiso 1 1 d D U . . .
O3A O 0.23111(17) 0.6834(2) 0.86963(15) 0.0130(3) Uani 1 1 d D . . . .
H6A H 0.149(3) 0.667(4) 0.810(2) 0.016 Uiso 1 1 d D U . . .
O4A O -0.07038(18) 0.5450(3) 0.88656(16) 0.0164(4) Uani 1 1 d . . . . .
O1B O 0.42851(18) -0.2047(3) 0.39070(15) 0.0145(4) Uani 1 1 d . . . . .
O2B O 0.73437(19) -0.0031(2) 0.63983(17) 0.0154(4) Uani 1 1 d D . . . .
H5B H 0.700(4) 0.097(3) 0.628(3) 0.018 Uiso 1 1 d D U . . .
O3B O 1.07609(18) -0.2235(3) 0.60626(16) 0.0194(4) Uani 1 1 d . . . . .
N1A N 0.5834(2) 0.4592(3) 0.8818(2) 0.0134(4) Uani 1 1 d D . . . .
H4B H 0.535(3) 0.408(4) 0.805(3) 0.016 Uiso 1 1 d D U . . .
H4A H 0.689(3) 0.493(4) 0.888(3) 0.016 Uiso 1 1 d D U . . .
N2A N -0.0139(2) 0.4837(3) 1.1233(2) 0.0147(5) Uani 1 1 d D . . . .
H7A H -0.111(3) 0.448(4) 1.131(3) 0.018 Uiso 1 1 d D U . . .
H7B H 0.059(3) 0.481(4) 1.197(2) 0.018 Uiso 1 1 d D U . . .
N1B N 0.4215(2) -0.1340(3) 0.6235(2) 0.0159(4) Uani 1 1 d D . . . .
H4C H 0.317(3) -0.168(4) 0.621(3) 0.019 Uiso 1 1 d D U . . .
H4D H 0.474(3) -0.092(4) 0.699(3) 0.019 Uiso 1 1 d D U . . .
N2B N 1.0121(2) -0.1608(3) 0.3731(2) 0.0154(5) Uani 1 1 d D . . . .
H7D H 0.940(3) -0.146(4) 0.306(3) 0.019 Uiso 1 1 d D U . . .
H7C H 1.112(3) -0.134(4) 0.364(3) 0.019 Uiso 1 1 d D U . . .
C1A C 0.5022(3) 0.4807(3) 0.9958(3) 0.0109(5) Uani 1 1 d . . . . .
C2A C 0.3191(3) 0.4243(3) 0.9873(2) 0.0111(5) Uani 1 1 d . . . . .
H2A H 0.302(3) 0.361(4) 1.067(3) 0.016(7) Uiso 1 1 d . . . . .
C3A C 0.2114(3) 0.5838(3) 0.9904(2) 0.0112(5) Uani 1 1 d . . . . .
H3A H 0.250(3) 0.643(4) 1.074(3) 0.012(6) Uiso 1 1 d . . . . .
C4A C 0.0274(2) 0.5357(3) 0.9963(3) 0.0116(5) Uani 1 1 d . . . . .
C1B C 0.4977(3) -0.1474(3) 0.5059(3) 0.0123(5) Uani 1 1 d . . . . .
C2B C 0.6814(3) -0.0931(3) 0.5132(2) 0.0128(5) Uani 1 1 d . . . . .
H2B H 0.689(3) -0.025(4) 0.430(3) 0.006(6) Uiso 1 1 d . . . . .
C3B C 0.7888(3) -0.2515(3) 0.5107(2) 0.0140(5) Uani 1 1 d . . . . .
H3B H 0.746(3) -0.322(5) 0.432(3) 0.013(6) Uiso 1 1 d . . . . .
H3C H 0.779(3) -0.313(4) 0.600(3) 0.010(6) Uiso 1 1 d . . . . .
C4B C 0.9720(3) -0.2107(3) 0.5001(3) 0.0129(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C1A 1.249(3) . ?
O2A C2A 1.412(3) . ?
O2A H5A 0.81(2) . ?
O3A C3A 1.405(3) . ?
O3A H6A 0.83(2) . ?
O4A C4A 1.232(3) . ?
O1B C1B 1.251(3) . ?
O2B C2B 1.416(3) . ?
O2B H5B 0.85(2) . ?
O3B C4B 1.238(3) . ?
N1A C1A 1.316(3) . ?
N1A H4B 0.88(2) . ?
N1A H4A 0.88(2) . ?
N2A C4A 1.332(3) . ?
N2A H7A 0.84(2) . ?
N2A H7B 0.86(2) . ?
N1B C1B 1.315(3) . ?
N1B H4C 0.88(2) . ?
N1B H4D 0.85(2) . ?
N2B C4B 1.324(3) . ?
N2B H7D 0.82(2) . ?
N2B H7C 0.84(2) . ?
C1A C2A 1.530(3) . ?
C2A C3A 1.541(3) . ?
C2A H2A 0.93(3) . ?
C3A C4A 1.531(3) . ?
C3A H3A 0.94(3) . ?
C1B C2B 1.531(3) . ?
C2B C3B 1.532(3) . ?
C2B H2B 0.96(3) . ?
C3B C4B 1.518(3) . ?
C3B H3B 0.96(3) . ?
C3B H3C 0.98(3) . ?

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
C2A O2A H5A 106(2) . . ?
C3A O3A H6A 108(2) . . ?
C2B O2B H5B 108(2) . . ?
C1A N1A H4B 120.6(17) . . ?
C1A N1A H4A 116.8(18) . . ?
H4B N1A H4A 122(2) . . ?
C4A N2A H7A 120.2(19) . . ?
C4A N2A H7B 121.1(19) . . ?
H7A N2A H7B 119(3) . . ?
C1B N1B H4C 118.3(18) . . ?
C1B N1B H4D 119.5(18) . . ?
H4C N1B H4D 122(2) . . ?
C4B N2B H7D 121(2) . . ?
C4B N2B H7C 119.1(19) . . ?
H7D N2B H7C 120(3) . . ?
O1A C1A N1A 124.4(2) . . ?
O1A C1A C2A 117.6(2) . . ?
N1A C1A C2A 118.0(2) . . ?
O2A C2A C1A 113.65(18) . . ?
O2A C2A C3A 108.35(18) . . ?
C1A C2A C3A 107.06(19) . . ?
O2A C2A H2A 109.8(19) . . ?
C1A C2A H2A 109.9(18) . . ?
C3A C2A H2A 107.9(19) . . ?
O3A C3A C4A 110.93(18) . . ?
O3A C3A C2A 110.17(17) . . ?
C4A C3A C2A 109.8(2) . . ?
O3A C3A H3A 109.5(18) . . ?
C4A C3A H3A 109.5(15) . . ?
C2A C3A H3A 106.8(18) . . ?
O4A C4A N2A 124.72(19) . . ?
O4A C4A C3A 119.4(2) . . ?
N2A C4A C3A 115.9(2) . . ?
O1B C1B N1B 123.3(2) . . ?
O1B C1B C2B 119.0(2) . . ?
N1B C1B C2B 117.7(2) . . ?
O2B C2B C1B 112.88(18) . . ?
O2B C2B C3B 108.02(18) . . ?
C1B C2B C3B 107.82(19) . . ?
O2B C2B H2B 110.9(16) . . ?
C1B C2B H2B 105.3(15) . . ?
C3B C2B H2B 112.0(16) . . ?
C4B C3B C2B 111.9(2) . . ?
C4B C3B H3B 110.5(14) . . ?
C2B C3B H3B 109.7(18) . . ?
C4B C3B H3C 108.9(13) . . ?
C2B C3B H3C 107.6(16) . . ?
H3B C3B H3C 108(3) . . ?
O3B C4B N2B 122.81(19) . . ?
O3B C4B C3B 120.7(2) . . ?
N2B C4B C3B 116.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1A C1A C2A O2A -173.1(2) . . . . ?
N1A C1A C2A O2A 8.1(3) . . . . ?
O1A C1A C2A C3A 67.3(3) . . . . ?
N1A C1A C2A C3A -111.5(2) . . . . ?
O2A C2A C3A O3A -60.1(2) . . . . ?
C1A C2A C3A O3A 62.8(2) . . . . ?
O2A C2A C3A C4A 62.3(2) . . . . ?
C1A C2A C3A C4A -174.73(17) . . . . ?
O3A C3A C4A O4A 19.3(3) . . . . ?
C2A C3A C4A O4A -102.7(3) . . . . ?
O3A C3A C4A N2A -161.6(2) . . . . ?
C2A C3A C4A N2A 76.4(3) . . . . ?
O1B C1B C2B O2B 169.1(2) . . . . ?
N1B C1B C2B O2B -12.2(3) . . . . ?
O1B C1B C2B C3B -71.7(3) . . . . ?
N1B C1B C2B C3B 107.0(2) . . . . ?
O2B C2B C3B C4B -64.3(2) . . . . ?
C1B C2B C3B C4B 173.40(18) . . . . ?
C2B C3B C4B O3B 104.6(3) . . . . ?
C2B C3B C4B N2B -75.0(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
N1A H4B O1B 0.88(2) 2.09(2) 2.862(2) 146(2) 2_656
N1A H4A O4A 0.88(2) 1.98(2) 2.857(2) 173(3) 1_655
N2A H7B O2B 0.86(2) 2.14(2) 2.996(2) 171(3) 2_657
N2A H7A O3A 0.84(2) 2.32(3) 2.969(3) 134(3) 2_547
N2B H7D O2A 0.82(2) 2.17(2) 2.973(2) 167(3) 2_646
N2B H7C O1B 0.84(2) 2.59(2) 3.347(2) 150(3) 1_655
N1B H4C O3B 0.88(2) 1.97(2) 2.851(2) 174(3) 1_455
N1B H4D O1A 0.85(2) 2.15(2) 2.876(3) 143(2) 2_647
O3A H6A O3B 0.83(2) 2.13(2) 2.753(2) 132(3) 1_465
O2A H5A O1A 0.81(2) 1.86(2) 2.670(2) 173(3) 2_647
O2B H5B O1B 0.85(2) 1.89(2) 2.719(3) 166(3) 2_656

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_17kaw12
_database_code_depnum_ccdc_archive 'CCDC 1832195'
_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-06-18 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         'C12 H24 N2 O4'
_chemical_formula_sum            'C12 H24 N2 O4'
_chemical_formula_weight         260.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   31.8791(12)
_cell_length_b                   5.0676(2)
_cell_length_c                   8.8564(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.049(4)
_cell_angle_gamma                90
_cell_volume                     1422.79(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6462
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      68.08

_exptl_crystal_description       'transparent plate'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.111
_exptl_absorpt_coefficient_mu    0.747
_shelx_estimated_absorpt_T_min   0.793
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
_exptl_absorpt_special_details   0


_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14676
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.788
_diffrn_reflns_theta_max         68.116
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1307
_reflns_number_gt                1211
_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       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (Uiso = 1.5xUeqiv for methyl groups). Those H 
 atoms attached to nitrogen or oxygen were
 located in Fourier diff maps and assigned Uiso = 1.2xUeqiv with 
 N-H and O-H bond distances restrained to 0.85(2) angstroms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²+1.3147P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1307
_refine_ls_number_parameters     89
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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 0.06627(3) 0.6279(2) 0.14988(11) 0.0261(3) Uani 1 1 d . . . . .
O2 O 0.02117(3) 0.1596(2) 0.39160(12) 0.0262(3) Uani 1 1 d . . . . .
H5 H 0.0330(6) 0.197(4) 0.474(2) 0.031 Uiso 1 1 d . U . . .
N1 N 0.07934(4) 0.1917(3) 0.19308(14) 0.0238(3) Uani 1 1 d . . . . .
H4 H 0.0704(6) 0.058(4) 0.228(2) 0.029 Uiso 1 1 d . U . . .
C1 C 0.05797(4) 0.4130(3) 0.20874(15) 0.0210(3) Uani 1 1 d . . . . .
C2 C 0.02059(4) 0.3948(3) 0.30443(15) 0.0214(3) Uani 1 1 d . . . . .
H2 H 0.0208 0.5510 0.3735 0.026 Uiso 1 1 calc R U . . .
C3 C 0.11363(5) 0.1678(3) 0.09573(18) 0.0285(4) Uani 1 1 d . . . . .
H3A H 0.1117 0.3151 0.0219 0.034 Uiso 1 1 calc R U . . .
H3B H 0.1102 0.0008 0.0377 0.034 Uiso 1 1 calc R U . . .
C4 C 0.15713(5) 0.1715(3) 0.1865(2) 0.0351(4) Uani 1 1 d . . . . .
H4A H 0.1580 0.0346 0.2665 0.042 Uiso 1 1 calc R U . . .
H4B H 0.1786 0.1250 0.1179 0.042 Uiso 1 1 calc R U . . .
C5 C 0.16865(5) 0.4365(4) 0.2604(2) 0.0409(5) Uani 1 1 d . . . . .
H5A H 0.1465 0.4872 0.3255 0.049 Uiso 1 1 calc R U . . .
H5B H 0.1692 0.5721 0.1802 0.049 Uiso 1 1 calc R U . . .
C6 C 0.21134(6) 0.4330(5) 0.3566(3) 0.0558(6) Uani 1 1 d . . . . .
H6A H 0.2105 0.3066 0.4400 0.084 Uiso 1 1 calc R U . . .
H6B H 0.2176 0.6095 0.3983 0.084 Uiso 1 1 calc R U . . .
H6C H 0.2333 0.3806 0.2933 0.084 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 C1 1.2476(17) . ?
O2 C2 1.4194(17) . ?
O2 H5 0.81(2) . ?
N1 C1 1.3273(19) . ?
N1 C3 1.4668(18) . ?
N1 H4 0.81(2) . ?
C1 C2 1.5359(19) . ?
C2 C2 1.545(3) 2 ?
C2 H2 1.0000 . ?
C3 C4 1.528(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.522(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.528(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 H5 105.9(14) . . ?
C1 N1 C3 123.63(13) . . ?
C1 N1 H4 117.5(13) . . ?
C3 N1 H4 118.1(13) . . ?
O1 C1 N1 124.06(13) . . ?
O1 C1 C2 119.60(12) . . ?
N1 C1 C2 116.33(12) . . ?
O2 C2 C1 112.60(11) . . ?
O2 C2 C2 107.50(9) . 2 ?
C1 C2 C2 108.26(13) . 2 ?
O2 C2 H2 109.5 . . ?
C1 C2 H2 109.5 . . ?
C2 C2 H2 109.5 2 . ?
N1 C3 C4 112.41(13) . . ?
N1 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
N1 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 113.68(14) . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C4 C5 C6 112.96(17) . . ?
C4 C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
C6 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 O1 -4.4(2) . . . . ?
C3 N1 C1 C2 174.80(12) . . . . ?
O1 C1 C2 O2 -166.15(12) . . . . ?
N1 C1 C2 O2 14.58(16) . . . . ?
O1 C1 C2 C2 75.14(12) . . . 2 ?
N1 C1 C2 C2 -104.13(11) . . . 2 ?
C1 N1 C3 C4 102.85(16) . . . . ?
N1 C3 C4 C5 -67.93(18) . . . . ?
C3 C4 C5 C6 177.35(15) . . . . ?

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 H4 O1 0.81(2) 2.29(2) 2.9067(17) 133.7(17) 1_545
O2 H5 O1 0.81(2) 2.00(2) 2.7868(15) 165.2(19) 6_566

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_16kaw53
_database_code_depnum_ccdc_archive 'CCDC 1832192'
_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-06-18 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         'C4 H8 N2 O3'
_chemical_formula_sum            'C4 H8 N2 O3'
_chemical_formula_weight         132.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   9.4044(2)
_cell_length_b                   8.2033(2)
_cell_length_c                   7.7750(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.659(1)
_cell_angle_gamma                90
_cell_volume                     587.44(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6297
_cell_measurement_theta_min      4.80
_cell_measurement_theta_max      68.30

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.136
_exptl_crystal_size_mid          0.265
_exptl_crystal_size_max          0.274
_exptl_absorpt_coefficient_mu    1.105
_shelx_estimated_absorpt_T_min   0.739
_shelx_estimated_absorpt_T_max   0.860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8515
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.801
_diffrn_reflns_theta_max         68.209
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1067
_reflns_number_gt                1049
_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       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms. Those H atoms attached to nitrogen or oxygen were
 located in Fourier diff maps and assigned Uiso = 1.2xUeqiv with 
 N-H and O-H bond distances restrained to 0.85(2) angstroms.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0555P)²+0.3136P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1067
_refine_ls_number_parameters     97
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0885
_refine_ls_wR_factor_gt          0.0882
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.008
_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 0.66371(9) -0.29208(11) 0.23699(13) 0.0183(3) Uani 1 1 d . . . . .
O2 O 0.70083(10) 0.13074(11) 0.34681(13) 0.0193(3) Uani 1 1 d D . . . .
H5 H 0.7694(17) 0.178(2) 0.422(2) 0.023 Uiso 1 1 d D U . . .
O3 O 0.92622(10) 0.24640(11) 0.07696(12) 0.0180(3) Uani 1 1 d . . . . .
N1 N 0.50135(12) -0.10324(15) 0.28600(15) 0.0190(3) Uani 1 1 d D . . . .
H4B H 0.4839(18) -0.0051(19) 0.305(2) 0.023 Uiso 1 1 d D U . . .
H4A H 0.4348(17) -0.177(2) 0.270(2) 0.023 Uiso 1 1 d D U . . .
N2 N 1.06052(11) 0.05181(14) 0.23664(14) 0.0152(3) Uani 1 1 d D . . . .
H7B H 1.1396(16) 0.1124(18) 0.247(2) 0.018 Uiso 1 1 d D U . . .
H7A H 1.0622(17) -0.0448(18) 0.279(2) 0.018 Uiso 1 1 d D U . . .
C1 C 0.63283(13) -0.15025(15) 0.27170(16) 0.0148(3) Uani 1 1 d . . . . .
C2 C 0.75229(13) -0.02117(15) 0.29730(16) 0.0145(3) Uani 1 1 d . . . . .
H2 H 0.8345 -0.0583 0.3917 0.017 Uiso 1 1 calc R U . . .
C3 C 0.80654(13) -0.00501(16) 0.12462(16) 0.0160(3) Uani 1 1 d . . . . .
H3A H 0.8338 -0.1140 0.0871 0.019 Uiso 1 1 calc R U . . .
H3B H 0.7272 0.0378 0.0321 0.019 Uiso 1 1 calc R U . . .
C4 C 0.93644(13) 0.10789(15) 0.14456(16) 0.0142(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2420(16) . ?
O2 C2 1.4179(15) . ?
O2 H5 0.866(14) . ?
O3 C4 1.2475(16) . ?
N1 C1 1.3212(17) . ?
N1 H4B 0.841(15) . ?
N1 H4A 0.861(14) . ?
N2 C4 1.3222(17) . ?
N2 H7B 0.884(13) . ?
N2 H7A 0.858(14) . ?
C1 C2 1.5273(17) . ?
C2 C3 1.5354(17) . ?
C2 H2 1.0000 . ?
C3 C4 1.5158(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?

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 O2 H5 108.9(11) . . ?
C1 N1 H4B 120.9(12) . . ?
C1 N1 H4A 116.6(12) . . ?
H4B N1 H4A 122.4(16) . . ?
C4 N2 H7B 119.3(11) . . ?
C4 N2 H7A 118.4(11) . . ?
H7B N2 H7A 122.2(15) . . ?
O1 C1 N1 123.75(12) . . ?
O1 C1 C2 118.67(11) . . ?
N1 C1 C2 117.58(11) . . ?
O2 C2 C1 111.24(10) . . ?
O2 C2 C3 110.70(10) . . ?
C1 C2 C3 108.15(10) . . ?
O2 C2 H2 108.9 . . ?
C1 C2 H2 108.9 . . ?
C3 C2 H2 108.9 . . ?
C4 C3 C2 111.51(10) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
O3 C4 N2 121.97(12) . . ?
O3 C4 C3 121.44(11) . . ?
N2 C4 C3 116.59(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O2 -176.29(10) . . . . ?
N1 C1 C2 O2 4.48(16) . . . . ?
O1 C1 C2 C3 61.94(14) . . . . ?
N1 C1 C2 C3 -117.29(12) . . . . ?
O2 C2 C3 C4 63.95(13) . . . . ?
C1 C2 C3 C4 -173.94(10) . . . . ?
C2 C3 C4 O3 -107.97(13) . . . . ?
C2 C3 C4 N2 72.17(14) . . . . ?

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 H4B O1 0.841(15) 2.215(15) 2.9740(15) 150.3(15) 2_655
N1 H4A O2 0.861(14) 2.115(15) 2.9411(15) 160.8(16) 2_645
N2 H7B O1 0.884(13) 1.990(14) 2.8623(14) 168.7(15) 2_755
N2 H7A O3 0.858(14) 2.036(14) 2.8844(14) 169.8(16) 2_745
O2 H5 O3 0.866(14) 1.817(15) 2.6791(13) 173.0(16) 4_566

_refine_diff_density_max         0.457
_refine_diff_density_min         -0.251
_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_kaw13
_database_code_depnum_ccdc_archive 'CCDC 1832198'
_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-06-18 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         'C12 H24 N2 O3, C12 H24 N2 O4'
_chemical_formula_sum            'C24 H48 N4 O7'
_chemical_formula_weight         504.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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'

_cell_length_a                   4.9064(3)
_cell_length_b                   8.7118(6)
_cell_length_c                   17.1527(14)
_cell_angle_alpha                102.543(7)
_cell_angle_beta                 96.249(5)
_cell_angle_gamma                90.472(5)
_cell_volume                     711.03(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6351
_cell_measurement_theta_max      66.056
_cell_measurement_theta_min      2.654

_exptl_crystal_description       'transparent plate'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_F_000             276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.704
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.5209
_exptl_absorpt_correction_T_min  0.4372
_exptl_absorpt_process_details   
;   
 SADABS-2014/5 (Bruker,2014/5) was used for absorption
 correction. wR2(int) was 0.0725 before and 0.0530
 after correction. The Ratio of minimum to maximum
 transmission is 0.8393. The λ/2 correction
 factor is 0.00150.
;
_exptl_absorpt_special_details   ?


_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_reflns_number            15213
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.656
_diffrn_reflns_theta_max         68.165
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_point_group_measured_fraction_full 0.920
_reflns_number_total             4727
_reflns_number_gt                4188
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_max     0.861
_reflns_Friedel_fraction_full    0.868

_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_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.10-0 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms. Those H atoms attached to nitrogen or oxygen were
 located in Fourier diff maps and assigned Uiso = 1.2xUeqiv with 
 N-H and O-H bond distances restrained to 0.85(2) angstroms.
;

_refine_ls_abs_structure_details 
;
 Flack x determined using 1793 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0599P)²+0.2364P] 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_Flack   0.16(10)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         4727
_refine_ls_number_parameters     323
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1207
_refine_ls_wR_factor_gt          0.1155
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
O1A O 0.2788(5) 0.7806(4) 0.3832(2) 0.0618(9) Uani 1 1 d . . . . .
O2A O -0.2527(5) 0.6353(3) 0.47530(19) 0.0457(7) Uani 1 1 d D . . . .
H5A H -0.2692 0.5511 0.4909 0.069 Uiso 1 1 calc DR U . . .
O3A O 0.0800(5) 0.9271(3) 0.55416(18) 0.0416(6) Uani 1 1 d D . . . .
H6A H 0.2141 0.9893 0.5736 0.062 Uiso 1 1 calc DR U . . .
O4A O 0.1875(5) 0.5773(3) 0.62943(17) 0.0427(7) Uani 1 1 d . . . . .
O1B O 0.5556(5) 0.0744(3) 0.63495(17) 0.0409(6) Uani 1 1 d . . . . .
O2B O 0.5898(5) 0.4202(3) 0.55720(17) 0.0379(6) Uani 1 1 d D . . . .
H5B H 0.4698 0.4796 0.5774 0.057 Uiso 1 1 calc DR U . . .
O4B O 0.1998(5) 0.2539(4) 0.39587(19) 0.0537(8) Uani 1 1 d . . . . .
N1A N -0.1795(6) 0.7776(4) 0.3605(2) 0.0396(8) Uani 1 1 d D . . . .
H4A H -0.3363 0.7499 0.3748 0.048 Uiso 1 1 calc DR U . . .
N2A N -0.0792(6) 0.7857(4) 0.66359(19) 0.0365(7) Uani 1 1 d D . . . .
H7A H -0.1402 0.8746 0.6531 0.044 Uiso 1 1 calc DR U . . .
N1B N 0.8591(6) 0.2806(4) 0.66413(19) 0.0350(7) Uani 1 1 d D . . . .
H4B H 0.9146 0.3676 0.6516 0.042 Uiso 1 1 calc DR U . . .
N2B N 0.6160(6) 0.2765(4) 0.3562(2) 0.0393(7) Uani 1 1 d D . . . .
H7B H 0.7914 0.2569 0.3638 0.047 Uiso 1 1 calc DR U . . .
C1A C 0.0508(7) 0.7464(5) 0.3999(2) 0.0393(9) Uani 1 1 d . . . . .
C2A C 0.0252(7) 0.6652(5) 0.4691(2) 0.0393(9) Uani 1 1 d . . . . .
H2A H 0.1204 0.5629 0.4585 0.047 Uiso 1 1 calc R U . . .
C3A C 0.1647(7) 0.7701(4) 0.5468(2) 0.0361(8) Uani 1 1 d . . . . .
H3A H 0.3679 0.7681 0.5456 0.043 Uiso 1 1 calc R U . . .
C4A C 0.0924(7) 0.7035(4) 0.6173(2) 0.0360(8) Uani 1 1 d . . . . .
C5A C -0.1828(9) 0.8564(5) 0.2940(3) 0.0491(10) Uani 1 1 d . . . . .
H5A1 H -0.0452 0.9447 0.3083 0.059 Uiso 1 1 calc R U . . .
H5A2 H -0.3655 0.9010 0.2849 0.059 Uiso 1 1 calc R U . . .
C6A C -0.1215(13) 0.7476(6) 0.2177(3) 0.0657(13) Uani 1 1 d . . . . .
H6A1 H 0.0516 0.6946 0.2288 0.079 Uiso 1 1 calc R U . . .
H6A2 H -0.2696 0.6655 0.2009 0.079 Uiso 1 1 calc R U . . .
C7A C -0.0949(15) 0.8264(8) 0.1497(3) 0.0800(17) Uani 1 1 d . . . . .
H7A1 H 0.0392 0.9159 0.1682 0.096 Uiso 1 1 calc R U . . .
H7A2 H -0.2741 0.8697 0.1346 0.096 Uiso 1 1 calc R U . . .
C8A C -0.0054(19) 0.7206(10) 0.0767(4) 0.107(2) Uani 1 1 d . . . . .
H8A1 H 0.1653 0.6711 0.0916 0.160 Uiso 1 1 calc R U . . .
H8A2 H 0.0253 0.7824 0.0368 0.160 Uiso 1 1 calc R U . . .
H8A3 H -0.1481 0.6391 0.0537 0.160 Uiso 1 1 calc R U . . .
C9A C -0.1681(8) 0.7311(5) 0.7313(2) 0.0419(9) Uani 1 1 d . . . . .
H9A1 H -0.0085 0.6895 0.7597 0.050 Uiso 1 1 calc R U . . .
H9A2 H -0.3048 0.6435 0.7108 0.050 Uiso 1 1 calc R U . . .
C10A C -0.2919(9) 0.8571(5) 0.7902(3) 0.0485(10) Uani 1 1 d . . . . .
H10A H -0.4555 0.8969 0.7628 0.058 Uiso 1 1 calc R U . . .
H10B H -0.1575 0.9460 0.8104 0.058 Uiso 1 1 calc R U . . .
C11A C -0.3733(11) 0.7947(6) 0.8599(3) 0.0605(12) Uani 1 1 d . . . . .
H11A H -0.5117 0.7081 0.8390 0.073 Uiso 1 1 calc R U . . .
H11B H -0.2103 0.7497 0.8848 0.073 Uiso 1 1 calc R U . . .
C12A C -0.4882(15) 0.9142(8) 0.9237(4) 0.087(2) Uani 1 1 d . . . . .
H12A H -0.3544 1.0017 0.9443 0.130 Uiso 1 1 calc R U . . .
H12B H -0.5272 0.8652 0.9678 0.130 Uiso 1 1 calc R U . . .
H12C H -0.6580 0.9539 0.9008 0.130 Uiso 1 1 calc R U . . .
C1B C 0.6435(7) 0.1973(4) 0.6203(2) 0.0333(8) Uani 1 1 d . . . . .
C2B C 0.5074(6) 0.2612(4) 0.5508(2) 0.0330(8) Uani 1 1 d . . . . .
H2B H 0.3040 0.2552 0.5514 0.040 Uiso 1 1 calc R U . . .
C3B C 0.5790(7) 0.1623(5) 0.4713(2) 0.0354(8) Uani 1 1 d . . . . .
H3B1 H 0.7805 0.1616 0.4707 0.043 Uiso 1 1 calc R U . . .
H3B2 H 0.5101 0.0525 0.4643 0.043 Uiso 1 1 calc R U . . .
C4B C 0.4477(7) 0.2329(4) 0.4040(2) 0.0360(8) Uani 1 1 d . . . . .
C5B C 1.0030(8) 0.2296(5) 0.7323(2) 0.0407(9) Uani 1 1 d . . . . .
H5B1 H 1.1209 0.1415 0.7120 0.049 Uiso 1 1 calc R U . . .
H5B2 H 0.8664 0.1892 0.7620 0.049 Uiso 1 1 calc R U . . .
C6B C 1.1763(9) 0.3558(5) 0.7891(3) 0.0466(10) Uani 1 1 d . . . . .
H6B1 H 1.0610 0.4454 0.8091 0.056 Uiso 1 1 calc R U . . .
H6B2 H 1.3188 0.3939 0.7606 0.056 Uiso 1 1 calc R U . . .
C7B C 1.3124(11) 0.2945(6) 0.8598(3) 0.0589(12) Uani 1 1 d . . . . .
H7B1 H 1.1677 0.2517 0.8858 0.071 Uiso 1 1 calc R U . . .
H7B2 H 1.4294 0.2064 0.8388 0.071 Uiso 1 1 calc R U . . .
C8B C 1.4840(15) 0.4129(8) 0.9222(4) 0.0857(19) Uani 1 1 d . . . . .
H8B1 H 1.6279 0.4570 0.8973 0.129 Uiso 1 1 calc R U . . .
H8B2 H 1.5684 0.3619 0.9641 0.129 Uiso 1 1 calc R U . . .
H8B3 H 1.3684 0.4975 0.9462 0.129 Uiso 1 1 calc R U . . .
C9B C 0.5229(9) 0.3546(5) 0.2924(3) 0.0488(10) Uani 1 1 d . . . . .
H9B1 H 0.6819 0.4092 0.2781 0.059 Uiso 1 1 calc R U . . .
H9B2 H 0.3914 0.4354 0.3123 0.059 Uiso 1 1 calc R U . . .
C10B C 0.3879(12) 0.2451(6) 0.2182(3) 0.0614(13) Uani 1 1 d . . . . .
H10C H 0.2329 0.1878 0.2327 0.074 Uiso 1 1 calc R U . . .
H10D H 0.5215 0.1665 0.1972 0.074 Uiso 1 1 calc R U . . .
C11B C 0.2820(14) 0.3274(7) 0.1523(3) 0.0763(16) Uani 1 1 d . . . . .
H11C H 0.1591 0.4112 0.1747 0.092 Uiso 1 1 calc R U . . .
H11D H 0.4394 0.3786 0.1354 0.092 Uiso 1 1 calc R U . . .
C12B C 0.1301(18) 0.2224(10) 0.0800(4) 0.099(2) Uani 1 1 d . . . . .
H12D H 0.2503 0.1397 0.0568 0.148 Uiso 1 1 calc R U . . .
H12E H 0.0712 0.2843 0.0401 0.148 Uiso 1 1 calc R U . . .
H12F H -0.0312 0.1745 0.0955 0.148 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
O1A C1A 1.234(5) . ?
O2A C2A 1.406(4) . ?
O2A H5A 0.8400 . ?
O3A C3A 1.416(5) . ?
O3A H6A 0.8400 . ?
O4A C4A 1.247(5) . ?
O1B C1B 1.236(5) . ?
O2B C2B 1.417(4) . ?
O2B H5B 0.8400 . ?
O4B C4B 1.229(4) . ?
N1A C1A 1.314(5) . ?
N1A C5A 1.452(6) . ?
N1A H4A 0.8800 . ?
N2A C4A 1.328(5) . ?
N2A C9A 1.453(5) . ?
N2A H7A 0.8800 . ?
N1B C1B 1.337(5) . ?
N1B C5B 1.454(5) . ?
N1B H4B 0.8800 . ?
N2B C4B 1.333(5) . ?
N2B C9B 1.446(5) . ?
N2B H7B 0.8800 . ?
C1A C2A 1.524(6) . ?
C2A C3A 1.531(6) . ?
C2A H2A 1.0000 . ?
C3A C4A 1.522(6) . ?
C3A H3A 1.0000 . ?
C5A C6A 1.501(7) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6A C7A 1.493(8) . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
C7A C8A 1.495(10) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
C9A C10A 1.502(6) . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C10A C11A 1.505(6) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A C12A 1.500(8) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C1B C2B 1.515(5) . ?
C2B C3B 1.525(5) . ?
C2B H2B 1.0000 . ?
C3B C4B 1.509(6) . ?
C3B H3B1 0.9900 . ?
C3B H3B2 0.9900 . ?
C5B C6B 1.490(6) . ?
C5B H5B1 0.9900 . ?
C5B H5B2 0.9900 . ?
C6B C7B 1.520(6) . ?
C6B H6B1 0.9900 . ?
C6B H6B2 0.9900 . ?
C7B C8B 1.493(8) . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C8B H8B1 0.9800 . ?
C8B H8B2 0.9800 . ?
C8B H8B3 0.9800 . ?
C9B C10B 1.499(7) . ?
C9B H9B1 0.9900 . ?
C9B H9B2 0.9900 . ?
C10B C11B 1.513(7) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B C12B 1.492(9) . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2A O2A H5A 109.5 . . ?
C3A O3A H6A 109.5 . . ?
C2B O2B H5B 109.5 . . ?
C1A N1A C5A 121.9(3) . . ?
C1A N1A H4A 119.0 . . ?
C5A N1A H4A 119.0 . . ?
C4A N2A C9A 121.0(3) . . ?
C4A N2A H7A 119.5 . . ?
C9A N2A H7A 119.5 . . ?
C1B N1B C5B 120.9(3) . . ?
C1B N1B H4B 119.5 . . ?
C5B N1B H4B 119.5 . . ?
C4B N2B C9B 122.9(3) . . ?
C4B N2B H7B 118.6 . . ?
C9B N2B H7B 118.6 . . ?
O1A C1A N1A 122.9(4) . . ?
O1A C1A C2A 120.4(3) . . ?
N1A C1A C2A 116.6(3) . . ?
O2A C2A C1A 110.0(3) . . ?
O2A C2A C3A 111.1(3) . . ?
C1A C2A C3A 108.9(3) . . ?
O2A C2A H2A 108.9 . . ?
C1A C2A H2A 108.9 . . ?
C3A C2A H2A 108.9 . . ?
O3A C3A C4A 111.1(3) . . ?
O3A C3A C2A 110.5(3) . . ?
C4A C3A C2A 108.3(3) . . ?
O3A C3A H3A 109.0 . . ?
C4A C3A H3A 109.0 . . ?
C2A C3A H3A 109.0 . . ?
O4A C4A N2A 122.5(4) . . ?
O4A C4A C3A 121.3(3) . . ?
N2A C4A C3A 116.3(3) . . ?
N1A C5A C6A 112.4(4) . . ?
N1A C5A H5A1 109.1 . . ?
C6A C5A H5A1 109.1 . . ?
N1A C5A H5A2 109.1 . . ?
C6A C5A H5A2 109.1 . . ?
H5A1 C5A H5A2 107.9 . . ?
C7A C6A C5A 114.4(5) . . ?
C7A C6A H6A1 108.7 . . ?
C5A C6A H6A1 108.7 . . ?
C7A C6A H6A2 108.7 . . ?
C5A C6A H6A2 108.7 . . ?
H6A1 C6A H6A2 107.6 . . ?
C6A C7A C8A 114.1(6) . . ?
C6A C7A H7A1 108.7 . . ?
C8A C7A H7A1 108.7 . . ?
C6A C7A H7A2 108.7 . . ?
C8A C7A H7A2 108.7 . . ?
H7A1 C7A H7A2 107.6 . . ?
C7A C8A H8A1 109.5 . . ?
C7A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C7A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
N2A C9A C10A 113.5(3) . . ?
N2A C9A H9A1 108.9 . . ?
C10A C9A H9A1 108.9 . . ?
N2A C9A H9A2 108.9 . . ?
C10A C9A H9A2 108.9 . . ?
H9A1 C9A H9A2 107.7 . . ?
C9A C10A C11A 111.1(4) . . ?
C9A C10A H10A 109.4 . . ?
C11A C10A H10A 109.4 . . ?
C9A C10A H10B 109.4 . . ?
C11A C10A H10B 109.4 . . ?
H10A C10A H10B 108.0 . . ?
C12A C11A C10A 114.8(5) . . ?
C12A C11A H11A 108.6 . . ?
C10A C11A H11A 108.6 . . ?
C12A C11A H11B 108.6 . . ?
C10A C11A H11B 108.6 . . ?
H11A C11A H11B 107.5 . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
O1B C1B N1B 122.6(3) . . ?
O1B C1B C2B 120.7(3) . . ?
N1B C1B C2B 116.7(3) . . ?
O2B C2B C1B 111.3(3) . . ?
O2B C2B C3B 109.3(3) . . ?
C1B C2B C3B 110.1(3) . . ?
O2B C2B H2B 108.7 . . ?
C1B C2B H2B 108.7 . . ?
C3B C2B H2B 108.7 . . ?
C4B C3B C2B 108.4(3) . . ?
C4B C3B H3B1 110.0 . . ?
C2B C3B H3B1 110.0 . . ?
C4B C3B H3B2 110.0 . . ?
C2B C3B H3B2 110.0 . . ?
H3B1 C3B H3B2 108.4 . . ?
O4B C4B N2B 122.0(4) . . ?
O4B C4B C3B 121.4(3) . . ?
N2B C4B C3B 116.5(3) . . ?
N1B C5B C6B 113.9(3) . . ?
N1B C5B H5B1 108.8 . . ?
C6B C5B H5B1 108.8 . . ?
N1B C5B H5B2 108.8 . . ?
C6B C5B H5B2 108.8 . . ?
H5B1 C5B H5B2 107.7 . . ?
C5B C6B C7B 110.7(4) . . ?
C5B C6B H6B1 109.5 . . ?
C7B C6B H6B1 109.5 . . ?
C5B C6B H6B2 109.5 . . ?
C7B C6B H6B2 109.5 . . ?
H6B1 C6B H6B2 108.1 . . ?
C8B C7B C6B 115.4(4) . . ?
C8B C7B H7B1 108.4 . . ?
C6B C7B H7B1 108.4 . . ?
C8B C7B H7B2 108.4 . . ?
C6B C7B H7B2 108.4 . . ?
H7B1 C7B H7B2 107.5 . . ?
C7B C8B H8B1 109.5 . . ?
C7B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
C7B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
H8B2 C8B H8B3 109.5 . . ?
N2B C9B C10B 113.6(4) . . ?
N2B C9B H9B1 108.8 . . ?
C10B C9B H9B1 108.8 . . ?
N2B C9B H9B2 108.8 . . ?
C10B C9B H9B2 108.8 . . ?
H9B1 C9B H9B2 107.7 . . ?
C9B C10B C11B 113.6(4) . . ?
C9B C10B H10C 108.8 . . ?
C11B C10B H10C 108.8 . . ?
C9B C10B H10D 108.8 . . ?
C11B C10B H10D 108.8 . . ?
H10C C10B H10D 107.7 . . ?
C12B C11B C10B 114.6(5) . . ?
C12B C11B H11C 108.6 . . ?
C10B C11B H11C 108.6 . . ?
C12B C11B H11D 108.6 . . ?
C10B C11B H11D 108.6 . . ?
H11C C11B H11D 107.6 . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5A N1A C1A O1A -0.4(6) . . . . ?
C5A N1A C1A C2A 179.2(4) . . . . ?
O1A C1A C2A O2A -178.7(4) . . . . ?
N1A C1A C2A O2A 1.7(5) . . . . ?
O1A C1A C2A C3A 59.3(5) . . . . ?
N1A C1A C2A C3A -120.3(4) . . . . ?
O2A C2A C3A O3A -73.7(4) . . . . ?
C1A C2A C3A O3A 47.6(4) . . . . ?
O2A C2A C3A C4A 48.2(4) . . . . ?
C1A C2A C3A C4A 169.6(3) . . . . ?
C9A N2A C4A O4A -0.6(6) . . . . ?
C9A N2A C4A C3A 178.4(3) . . . . ?
O3A C3A C4A O4A -168.1(3) . . . . ?
C2A C3A C4A O4A 70.3(4) . . . . ?
O3A C3A C4A N2A 12.8(4) . . . . ?
C2A C3A C4A N2A -108.7(4) . . . . ?
C1A N1A C5A C6A 78.1(5) . . . . ?
N1A C5A C6A C7A -174.2(4) . . . . ?
C5A C6A C7A C8A 174.0(6) . . . . ?
C4A N2A C9A C10A 163.2(4) . . . . ?
N2A C9A C10A C11A -178.6(4) . . . . ?
C9A C10A C11A C12A 177.5(5) . . . . ?
C5B N1B C1B O1B 0.1(5) . . . . ?
C5B N1B C1B C2B 179.7(3) . . . . ?
O1B C1B C2B O2B 164.4(3) . . . . ?
N1B C1B C2B O2B -15.3(4) . . . . ?
O1B C1B C2B C3B -74.2(4) . . . . ?
N1B C1B C2B C3B 106.2(3) . . . . ?
O2B C2B C3B C4B -55.5(4) . . . . ?
C1B C2B C3B C4B -178.1(3) . . . . ?
C9B N2B C4B O4B 1.3(6) . . . . ?
C9B N2B C4B C3B -176.1(3) . . . . ?
C2B C3B C4B O4B -55.5(4) . . . . ?
C2B C3B C4B N2B 121.9(3) . . . . ?
C1B N1B C5B C6B -161.9(3) . . . . ?
N1B C5B C6B C7B 178.3(4) . . . . ?
C5B C6B C7B C8B -178.0(5) . . . . ?
C4B N2B C9B C10B -78.7(5) . . . . ?
N2B C9B C10B C11B 178.1(4) . . . . ?
C9B C10B C11B C12B -176.1(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
N1A H4A O1A 0.88 1.93 2.728(4) 150.7 1_455
N2A H7A O1B 0.88 2.35 3.194(4) 160.1 1_465
O2A H5A O2B 0.84 1.95 2.727(4) 154.0 1_455
O3A H6A O1B 0.84 1.93 2.736(4) 160.8 1_565
N1B H4B O4A 0.88 2.38 3.231(4) 163.8 1_655
N2B H7B O4B 0.88 2.02 2.890(4) 168.8 1_655
O2B H5B O4A 0.84 1.84 2.673(4) 169.0 .

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.038

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

data_16kaw102
_database_code_depnum_ccdc_archive 'CCDC 1832196'
_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-06-18 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         'C6 H12 N2 O4'
_chemical_formula_sum            'C6 H12 N2 O4'
_chemical_formula_weight         176.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

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

_cell_length_a                   9.8954(4)
_cell_length_b                   19.3100(9)
_cell_length_c                   8.9868(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1717.20(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7340
_cell_measurement_theta_min      4.58
_cell_measurement_theta_max      67.73

_exptl_crystal_description       'transparent needle'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.983
_shelx_estimated_absorpt_T_min   0.762
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.675
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24009
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.580
_diffrn_reflns_theta_max         68.187
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1570
_reflns_number_gt                1318
_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       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms. Those H atoms attached to nitrogen or oxygen were
 located in Fourier diff maps and assigned Uiso = 1.2xUeqiv with 
 N-H and O-H bond distances restrained to 0.85(2) angstroms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0597P)²+1.0194P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1570
_refine_ls_number_parameters     127
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1060
_refine_ls_wR_factor_gt          0.0996
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.101
_refine_ls_shift/su_mean         0.002

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 0.56949(12) 0.31271(6) 0.41424(12) 0.0183(3) Uani 1 1 d . . . . .
O2 O 0.67988(12) 0.33774(6) 0.03577(13) 0.0201(3) Uani 1 1 d D . . . .
H5 H 0.7626(19) 0.3330(13) 0.007(3) 0.048(7) Uiso 1 1 d D . . . .
O3 O 0.50784(12) 0.44072(6) 0.15536(14) 0.0193(3) Uani 1 1 d D . . . .
H6 H 0.464(3) 0.4690(12) 0.214(3) 0.050(8) Uiso 1 1 d D . . . .
O4 O 0.86858(12) 0.46740(6) 0.18518(14) 0.0230(3) Uani 1 1 d . . . . .
N1 N 0.52504(14) 0.25466(8) 0.19827(16) 0.0187(3) Uani 1 1 d D . . . .
H4 H 0.541(2) 0.2506(12) 0.1046(19) 0.031(6) Uiso 1 1 d D . . . .
N2 N 0.70343(15) 0.52927(8) 0.06809(17) 0.0211(3) Uani 1 1 d D . . . .
H7 H 0.6200(16) 0.5296(11) 0.045(2) 0.026(5) Uiso 1 1 d D . . . .
C1 C 0.58516(16) 0.30457(8) 0.27632(18) 0.0152(4) Uani 1 1 d . . . . .
C2 C 0.68031(16) 0.35302(8) 0.19070(18) 0.0155(4) Uani 1 1 d . . . . .
H2 H 0.7741 0.3464 0.2295 0.019 Uiso 1 1 calc R U . . .
C3 C 0.63811(16) 0.42883(9) 0.21806(19) 0.0166(4) Uani 1 1 d . . . . .
H3 H 0.6327 0.4367 0.3279 0.020 Uiso 1 1 calc R U . . .
C4 C 0.74685(18) 0.47720(8) 0.15360(18) 0.0175(4) Uani 1 1 d . . . . .
C5 C 0.79548(19) 0.58013(10) 0.0020(2) 0.0270(4) Uani 1 1 d . . . . .
H5A H 0.8289 0.6114 0.0797 0.040 Uiso 1 1 calc R U . . .
H5B H 0.7472 0.6070 -0.0737 0.040 Uiso 1 1 calc R U . . .
H5C H 0.8719 0.5560 -0.0442 0.040 Uiso 1 1 calc R U . . .
C6 C 0.43948(19) 0.20161(10) 0.2671(2) 0.0252(4) Uani 1 1 d . . . . .
H6A H 0.4664 0.1952 0.3711 0.038 Uiso 1 1 calc R U . . .
H6B H 0.4500 0.1578 0.2133 0.038 Uiso 1 1 calc R U . . .
H6C H 0.3448 0.2163 0.2629 0.038 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 C1 1.259(2) . ?
O2 C2 1.423(2) . ?
O2 H5 0.862(17) . ?
O3 C3 1.425(2) . ?
O3 H6 0.874(17) . ?
O4 C4 1.252(2) . ?
N1 C1 1.332(2) . ?
N1 C6 1.466(2) . ?
N1 H4 0.861(16) . ?
N2 C4 1.337(2) . ?
N2 C5 1.465(2) . ?
N2 H7 0.851(16) . ?
C1 C2 1.534(2) . ?
C2 C3 1.542(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.538(2) . ?
C3 H3 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 H5 108.0(18) . . ?
C3 O3 H6 107.8(18) . . ?
C1 N1 C6 122.78(15) . . ?
C1 N1 H4 119.8(15) . . ?
C6 N1 H4 117.2(15) . . ?
C4 N2 C5 122.51(15) . . ?
C4 N2 H7 117.2(15) . . ?
C5 N2 H7 120.0(15) . . ?
O1 C1 N1 123.61(15) . . ?
O1 C1 C2 119.56(14) . . ?
N1 C1 C2 116.82(14) . . ?
O2 C2 C1 111.24(13) . . ?
O2 C2 C3 110.61(13) . . ?
C1 C2 C3 109.44(13) . . ?
O2 C2 H2 108.5 . . ?
C1 C2 H2 108.5 . . ?
C3 C2 H2 108.5 . . ?
O3 C3 C4 112.70(13) . . ?
O3 C3 C2 109.56(13) . . ?
C4 C3 C2 109.09(13) . . ?
O3 C3 H3 108.5 . . ?
C4 C3 H3 108.5 . . ?
C2 C3 H3 108.5 . . ?
O4 C4 N2 123.60(16) . . ?
O4 C4 C3 119.73(15) . . ?
N2 C4 C3 116.65(15) . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C1 O1 -3.3(3) . . . . ?
C6 N1 C1 C2 175.44(15) . . . . ?
O1 C1 C2 O2 -177.32(14) . . . . ?
N1 C1 C2 O2 3.9(2) . . . . ?
O1 C1 C2 C3 -54.79(19) . . . . ?
N1 C1 C2 C3 126.43(15) . . . . ?
O2 C2 C3 O3 57.50(17) . . . . ?
C1 C2 C3 O3 -65.40(16) . . . . ?
O2 C2 C3 C4 -66.30(16) . . . . ?
C1 C2 C3 C4 170.80(13) . . . . ?
C5 N2 C4 O4 0.3(3) . . . . ?
C5 N2 C4 C3 178.68(15) . . . . ?
O3 C3 C4 O4 -171.69(14) . . . . ?
C2 C3 C4 O4 -49.8(2) . . . . ?
O3 C3 C4 N2 9.9(2) . . . . ?
C2 C3 C4 N2 131.80(15) . . . . ?

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 H4 O1 0.861(16) 2.121(18) 2.8985(18) 150(2) 8_565
N2 H7 O3 0.851(16) 2.274(19) 2.9562(19) 137.2(19) 5_665
O2 H5 O1 0.862(17) 1.901(18) 2.7527(17) 169(3) 7_755
O3 H6 O4 0.874(17) 1.795(18) 2.6646(17) 173(3) 3_465

_refine_diff_density_max         0.289
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_17kaw05b
_database_code_depnum_ccdc_archive 'CCDC 1832193'
_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-06-18 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         'C6 H12 N2 O4, C6 H12 N2 O3'
_chemical_formula_sum            'C12 H24 N4 O7'
_chemical_formula_weight         336.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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'

_cell_length_a                   5.0193(3)
_cell_length_b                   8.6051(6)
_cell_length_c                   10.2069(7)
_cell_angle_alpha                69.005(4)
_cell_angle_beta                 77.721(4)
_cell_angle_gamma                89.513(4)
_cell_volume                     401.06(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6764
_cell_measurement_theta_min      4.76
_cell_measurement_theta_max      68.35

_exptl_crystal_description       'transparent plate'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_F_000             180
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.378
_exptl_crystal_size_min          0.082
_exptl_absorpt_coefficient_mu    0.976
_shelx_estimated_absorpt_T_min   0.692
_shelx_estimated_absorpt_T_max   0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.538
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker'
_exptl_absorpt_special_details   ?


_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8655
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.762
_diffrn_reflns_theta_max         68.234
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_point_group_measured_fraction_full 0.868
_reflns_number_total             2517
_reflns_number_gt                2467
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_max     0.746
_reflns_Friedel_fraction_full    0.753

_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       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms. Those H atoms attached to nitrogen or oxygen were
 located in Fourier diff maps and assigned Uiso = 1.2xUeqiv with 
 N-H and O-H bond distances restrained to 0.85(2) angstroms.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0796P)²+0.0055P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1030 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(10)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2517
_refine_ls_number_parameters     240
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0960
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.044
_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
O1A O 0.7267(4) 0.2774(2) 0.55199(18) 0.0204(4) Uani 1 1 d . . . . .
O2A O 0.6202(4) -0.1714(2) 0.68883(19) 0.0210(4) Uani 1 1 d D . . . .
H5A H 0.766(6) -0.192(5) 0.644(4) 0.034(10) Uiso 1 1 d D . . . .
O3A O 0.2351(4) 0.0264(2) 0.82461(19) 0.0199(4) Uani 1 1 d D . . . .
H6A H 0.206(9) 0.126(3) 0.801(4) 0.042(11) Uiso 1 1 d D . . . .
O4A O 0.7097(4) -0.2274(2) 1.0044(2) 0.0249(4) Uani 1 1 d . . . . .
O1B O 1.1254(4) -0.2113(2) 0.53872(19) 0.0203(4) Uani 1 1 d . . . . .
O2B O 1.0972(4) -0.6585(2) 0.68205(18) 0.0203(4) Uani 1 1 d D . . . .
H5B H 0.985(7) -0.687(5) 0.645(4) 0.030(9) Uiso 1 1 d D . . . .
O3B O 0.6827(4) -0.6909(2) 0.9833(2) 0.0264(5) Uani 1 1 d . . . . .
N1A N 0.4909(4) 0.0981(3) 0.4922(2) 0.0193(5) Uani 1 1 d D . . . .
H4A H 0.420(8) 0.001(3) 0.520(4) 0.033(10) Uiso 1 1 d D . . . .
N2A N 0.2532(4) -0.2542(3) 1.0281(2) 0.0189(5) Uani 1 1 d D . . . .
H7A H 0.121(5) -0.206(4) 0.997(3) 0.010(7) Uiso 1 1 d D . . . .
N1B N 1.4213(5) -0.3967(3) 0.4925(2) 0.0202(5) Uani 1 1 d D . . . .
H4B H 1.450(8) -0.500(3) 0.515(4) 0.033(9) Uiso 1 1 d D . . . .
N2B N 1.0977(4) -0.7558(3) 1.0320(2) 0.0201(5) Uani 1 1 d D . . . .
H7B H 1.266(5) -0.730(5) 1.012(4) 0.031(9) Uiso 1 1 d D . . . .
C1A C 0.6379(5) 0.1320(3) 0.5738(2) 0.0171(5) Uani 1 1 d . . . . .
C2A C 0.6889(5) -0.0183(3) 0.7020(3) 0.0176(5) Uani 1 1 d . . . . .
H2A H 0.8855 -0.0126 0.7065 0.021 Uiso 1 1 calc R U . . .
C3A C 0.5057(5) -0.0073(3) 0.8412(3) 0.0178(5) Uani 1 1 d . . . . .
H3A H 0.5852 0.0839 0.8637 0.021 Uiso 1 1 calc R U . . .
C4A C 0.4989(5) -0.1740(3) 0.9661(3) 0.0185(5) Uani 1 1 d . . . . .
C5A C 0.2175(5) -0.4174(3) 1.1437(3) 0.0214(6) Uani 1 1 d . . . . .
H5A1 H 0.2256 -0.4038 1.2341 0.032 Uiso 1 1 calc R U . . .
H5A2 H 0.3633 -0.4862 1.1206 0.032 Uiso 1 1 calc R U . . .
H5A3 H 0.0397 -0.4720 1.1540 0.032 Uiso 1 1 calc R U . . .
C6A C 0.4142(6) 0.2268(3) 0.3712(3) 0.0241(6) Uani 1 1 d . . . . .
H6A1 H 0.5556 0.3196 0.3287 0.036 Uiso 1 1 calc R U . . .
H6A2 H 0.2395 0.2673 0.4048 0.036 Uiso 1 1 calc R U . . .
H6A3 H 0.3957 0.1802 0.2986 0.036 Uiso 1 1 calc R U . . .
C1B C 1.1966(5) -0.3561(3) 0.5663(2) 0.0181(5) Uani 1 1 d . . . . .
C2B C 1.0247(5) -0.5026(3) 0.6932(3) 0.0181(5) Uani 1 1 d . . . . .
H2B H 0.8268 -0.4905 0.6921 0.022 Uiso 1 1 calc R U . . .
C3B C 1.0716(5) -0.4977(3) 0.8361(3) 0.0208(5) Uani 1 1 d . . . . .
H3B1 H 1.2699 -0.4911 0.8326 0.025 Uiso 1 1 calc R U . . .
H3B2 H 0.9936 -0.3983 0.8522 0.025 Uiso 1 1 calc R U . . .
C4B C 0.9324(5) -0.6564(3) 0.9580(3) 0.0196(5) Uani 1 1 d . . . . .
C5B C 0.9975(6) -0.9173(4) 1.1454(3) 0.0252(6) Uani 1 1 d . . . . .
H5B1 H 0.8747 -0.9761 1.1128 0.038 Uiso 1 1 calc R U . . .
H5B2 H 0.8981 -0.9000 1.2321 0.038 Uiso 1 1 calc R U . . .
H5B3 H 1.1526 -0.9841 1.1673 0.038 Uiso 1 1 calc R U . . .
C6B C 1.6074(6) -0.2719(4) 0.3699(3) 0.0247(6) Uani 1 1 d . . . . .
H6B1 H 1.7565 -0.2355 0.4030 0.037 Uiso 1 1 calc R U . . .
H6B2 H 1.5069 -0.1757 0.3265 0.037 Uiso 1 1 calc R U . . .
H6B3 H 1.6830 -0.3211 0.2981 0.037 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
O1A C1A 1.258(3) . ?
O2A C2A 1.423(3) . ?
O2A H5A 0.83(2) . ?
O3A C3A 1.419(3) . ?
O3A H6A 0.83(2) . ?
O4A C4A 1.234(3) . ?
O1B C1B 1.242(3) . ?
O2B C2B 1.424(3) . ?
O2B H5B 0.82(2) . ?
O3B C4B 1.241(4) . ?
N1A C1A 1.328(3) . ?
N1A C6A 1.454(3) . ?
N1A H4A 0.83(2) . ?
N2A C4A 1.330(3) . ?
N2A C5A 1.457(3) . ?
N2A H7A 0.84(2) . ?
N1B C1B 1.335(3) . ?
N1B C6B 1.466(3) . ?
N1B H4B 0.85(2) . ?
N2B C4B 1.335(4) . ?
N2B C5B 1.461(3) . ?
N2B H7B 0.84(3) . ?
C1A C2A 1.541(3) . ?
C2A C3A 1.553(3) . ?
C2A H2A 1.0000 . ?
C3A C4A 1.535(3) . ?
C3A H3A 1.0000 . ?
C5A H5A1 0.9800 . ?
C5A H5A2 0.9800 . ?
C5A H5A3 0.9800 . ?
C6A H6A1 0.9800 . ?
C6A H6A2 0.9800 . ?
C6A H6A3 0.9800 . ?
C1B C2B 1.544(3) . ?
C2B C3B 1.540(4) . ?
C2B H2B 1.0000 . ?
C3B C4B 1.526(4) . ?
C3B H3B1 0.9900 . ?
C3B H3B2 0.9900 . ?
C5B H5B1 0.9800 . ?
C5B H5B2 0.9800 . ?
C5B H5B3 0.9800 . ?
C6B H6B1 0.9800 . ?
C6B H6B2 0.9800 . ?
C6B H6B3 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2A O2A H5A 104(3) . . ?
C3A O3A H6A 114(3) . . ?
C2B O2B H5B 107(3) . . ?
C1A N1A C6A 122.7(2) . . ?
C1A N1A H4A 117(3) . . ?
C6A N1A H4A 119(3) . . ?
C4A N2A C5A 121.4(2) . . ?
C4A N2A H7A 116(2) . . ?
C5A N2A H7A 122(2) . . ?
C1B N1B C6B 122.3(2) . . ?
C1B N1B H4B 118(3) . . ?
C6B N1B H4B 120(3) . . ?
C4B N2B C5B 122.0(2) . . ?
C4B N2B H7B 121(3) . . ?
C5B N2B H7B 117(3) . . ?
O1A C1A N1A 123.1(2) . . ?
O1A C1A C2A 120.9(2) . . ?
N1A C1A C2A 116.0(2) . . ?
O2A C2A C1A 110.9(2) . . ?
O2A C2A C3A 109.6(2) . . ?
C1A C2A C3A 107.48(18) . . ?
O2A C2A H2A 109.6 . . ?
C1A C2A H2A 109.6 . . ?
C3A C2A H2A 109.6 . . ?
O3A C3A C4A 109.2(2) . . ?
O3A C3A C2A 111.2(2) . . ?
C4A C3A C2A 108.86(19) . . ?
O3A C3A H3A 109.2 . . ?
C4A C3A H3A 109.2 . . ?
C2A C3A H3A 109.2 . . ?
O4A C4A N2A 123.4(2) . . ?
O4A C4A C3A 121.2(2) . . ?
N2A C4A C3A 115.4(2) . . ?
N2A C5A H5A1 109.5 . . ?
N2A C5A H5A2 109.5 . . ?
H5A1 C5A H5A2 109.5 . . ?
N2A C5A H5A3 109.5 . . ?
H5A1 C5A H5A3 109.5 . . ?
H5A2 C5A H5A3 109.5 . . ?
N1A C6A H6A1 109.5 . . ?
N1A C6A H6A2 109.5 . . ?
H6A1 C6A H6A2 109.5 . . ?
N1A C6A H6A3 109.5 . . ?
H6A1 C6A H6A3 109.5 . . ?
H6A2 C6A H6A3 109.5 . . ?
O1B C1B N1B 123.9(2) . . ?
O1B C1B C2B 120.5(2) . . ?
N1B C1B C2B 115.6(2) . . ?
O2B C2B C3B 109.6(2) . . ?
O2B C2B C1B 110.91(19) . . ?
C3B C2B C1B 109.4(2) . . ?
O2B C2B H2B 109.0 . . ?
C3B C2B H2B 109.0 . . ?
C1B C2B H2B 109.0 . . ?
C4B C3B C2B 108.4(2) . . ?
C4B C3B H3B1 110.0 . . ?
C2B C3B H3B1 110.0 . . ?
C4B C3B H3B2 110.0 . . ?
C2B C3B H3B2 110.0 . . ?
H3B1 C3B H3B2 108.4 . . ?
O3B C4B N2B 122.9(3) . . ?
O3B C4B C3B 121.5(2) . . ?
N2B C4B C3B 115.6(2) . . ?
N2B C5B H5B1 109.5 . . ?
N2B C5B H5B2 109.5 . . ?
H5B1 C5B H5B2 109.5 . . ?
N2B C5B H5B3 109.5 . . ?
H5B1 C5B H5B3 109.5 . . ?
H5B2 C5B H5B3 109.5 . . ?
N1B C6B H6B1 109.5 . . ?
N1B C6B H6B2 109.5 . . ?
H6B1 C6B H6B2 109.5 . . ?
N1B C6B H6B3 109.5 . . ?
H6B1 C6B H6B3 109.5 . . ?
H6B2 C6B H6B3 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A C1A O1A -1.2(3) . . . . ?
C6A N1A C1A C2A 177.1(2) . . . . ?
O1A C1A C2A O2A -168.2(2) . . . . ?
N1A C1A C2A O2A 13.5(3) . . . . ?
O1A C1A C2A C3A 72.0(3) . . . . ?
N1A C1A C2A C3A -106.3(2) . . . . ?
O2A C2A C3A O3A -74.1(2) . . . . ?
C1A C2A C3A O3A 46.5(3) . . . . ?
O2A C2A C3A C4A 46.3(3) . . . . ?
C1A C2A C3A C4A 166.9(2) . . . . ?
C5A N2A C4A O4A -2.7(4) . . . . ?
C5A N2A C4A C3A 177.2(2) . . . . ?
O3A C3A C4A O4A -177.6(2) . . . . ?
C2A C3A C4A O4A 60.8(3) . . . . ?
O3A C3A C4A N2A 2.5(3) . . . . ?
C2A C3A C4A N2A -119.1(2) . . . . ?
C6B N1B C1B O1B -0.2(4) . . . . ?
C6B N1B C1B C2B -179.5(2) . . . . ?
O1B C1B C2B O2B 164.1(2) . . . . ?
N1B C1B C2B O2B -16.6(3) . . . . ?
O1B C1B C2B C3B -74.9(3) . . . . ?
N1B C1B C2B C3B 104.4(2) . . . . ?
O2B C2B C3B C4B -50.4(3) . . . . ?
C1B C2B C3B C4B -172.15(19) . . . . ?
C5B N2B C4B O3B 2.6(4) . . . . ?
C5B N2B C4B C3B -175.8(2) . . . . ?
C2B C3B C4B O3B -60.0(3) . . . . ?
C2B C3B C4B N2B 118.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1A H4A O1B 0.83(2) 2.29(3) 3.080(3) 158(4) 1_455
N2A H7A O4A 0.84(2) 2.06(3) 2.790(3) 146(3) 1_455
N1B H4B O1A 0.85(2) 2.32(3) 3.112(3) 154(4) 1_645
N2B H7B O3B 0.84(3) 2.06(3) 2.897(3) 173(4) 1_655
O2A H5A O1B 0.83(2) 1.93(3) 2.758(2) 172(4) .
O3A H6A O2B 0.83(2) 1.96(3) 2.742(2) 157(4) 1_465
O2B H5B O1A 0.82(2) 1.85(3) 2.668(3) 173(4) 1_545

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_17kaw03
_database_code_depnum_ccdc_archive 'CCDC 1832197'
_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-06-18 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         'C6 H12 N2 O3'
_chemical_formula_sum            'C6 H12 N2 O3'
_chemical_formula_weight         160.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   19.637(4)
_cell_length_b                   4.9347(13)
_cell_length_c                   8.4645(17)
_cell_angle_alpha                90
_cell_angle_beta                 92.281(12)
_cell_angle_gamma                90
_cell_volume                     819.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2865
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      67.48

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.052
_exptl_absorpt_coefficient_mu    0.881
_shelx_estimated_absorpt_T_min   0.741
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.578
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10151
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.252
_diffrn_reflns_theta_max         65.060
_diffrn_reflns_theta_full        65.060
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             1369
_reflns_number_gt                1122
_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       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms. Those H atoms attached to nitrogen or oxygen were
 located in Fourier diff maps and assigned Uiso = 1.2xUeqiv with 
 N-H and O-H bond distances restrained to 0.85(2) angstroms.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1596P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1369
_refine_ls_number_parameters     114
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.2231
_refine_ls_wR_factor_gt          0.1894
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.136
_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 0.13732(9) 0.5576(4) 0.02067(19) 0.0383(6) Uani 1 1 d . . . . .
O2 O 0.20919(10) 0.5060(4) -0.3619(2) 0.0394(6) Uani 1 1 d D . . . .
H5 H 0.188(2) 0.642(6) -0.409(5) 0.080(13) Uiso 1 1 d D . . . .
O3 O 0.34985(11) 0.8049(4) -0.2352(3) 0.0517(7) Uani 1 1 d . . . . .
N1 N 0.11606(11) 0.2745(5) -0.1864(2) 0.0361(6) Uani 1 1 d D . . . .
H4 H 0.128(2) 0.222(8) -0.278(3) 0.066(11) Uiso 1 1 d D . . . .
N2 N 0.37938(11) 0.3677(5) -0.2770(3) 0.0399(6) Uani 1 1 d D . . . .
H7 H 0.369(2) 0.202(5) -0.263(6) 0.100(17) Uiso 1 1 d D . . . .
C1 C 0.15221(13) 0.4667(5) -0.1122(3) 0.0322(7) Uani 1 1 d . . . . .
C2 C 0.21336(13) 0.5753(5) -0.1988(3) 0.0318(6) Uani 1 1 d . . . . .
H2 H 0.2144 0.7772 -0.1887 0.038 Uiso 1 1 calc R U . . .
C3 C 0.27972(14) 0.4592(6) -0.1248(3) 0.0374(7) Uani 1 1 d . . . . .
H3A H 0.2852 0.5179 -0.0131 0.045 Uiso 1 1 calc R U . . .
H3B H 0.2781 0.2587 -0.1271 0.045 Uiso 1 1 calc R U . . .
C4 C 0.33943(13) 0.5586(5) -0.2167(3) 0.0352(7) Uani 1 1 d . . . . .
C5 C 0.43612(15) 0.4338(7) -0.3765(4) 0.0520(8) Uani 1 1 d . . . . .
H5A H 0.4206 0.5605 -0.4596 0.078 Uiso 1 1 calc R U . . .
H5B H 0.4530 0.2678 -0.4250 0.078 Uiso 1 1 calc R U . . .
H5C H 0.4729 0.5176 -0.3118 0.078 Uiso 1 1 calc R U . . .
C6 C 0.05710(14) 0.1458(6) -0.1185(3) 0.0428(7) Uani 1 1 d . . . . .
H6A H 0.0726 0.0062 -0.0429 0.064 Uiso 1 1 calc R U . . .
H6B H 0.0287 0.0623 -0.2029 0.064 Uiso 1 1 calc R U . . .
H6C H 0.0304 0.2823 -0.0640 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 C1 1.256(3) . ?
O2 C2 1.422(3) . ?
O2 H5 0.873(19) . ?
O3 C4 1.243(3) . ?
N1 C1 1.328(3) . ?
N1 C6 1.459(3) . ?
N1 H4 0.852(19) . ?
N2 C4 1.340(4) . ?
N2 C5 1.460(4) . ?
N2 H7 0.85(2) . ?
C1 C2 1.528(3) . ?
C2 C3 1.534(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.514(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 H5 105(3) . . ?
C1 N1 C6 122.9(2) . . ?
C1 N1 H4 119(3) . . ?
C6 N1 H4 118(3) . . ?
C4 N2 C5 122.3(3) . . ?
C4 N2 H7 118(3) . . ?
C5 N2 H7 119(3) . . ?
O1 C1 N1 122.6(2) . . ?
O1 C1 C2 121.3(2) . . ?
N1 C1 C2 116.1(2) . . ?
O2 C2 C1 111.4(2) . . ?
O2 C2 C3 108.8(2) . . ?
C1 C2 C3 110.1(2) . . ?
O2 C2 H2 108.8 . . ?
C1 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
C4 C3 C2 109.4(2) . . ?
C4 C3 H3A 109.8 . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
C2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
O3 C4 N2 122.5(2) . . ?
O3 C4 C3 121.1(3) . . ?
N2 C4 C3 116.4(2) . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C1 O1 -1.9(4) . . . . ?
C6 N1 C1 C2 178.7(2) . . . . ?
O1 C1 C2 O2 -162.7(2) . . . . ?
N1 C1 C2 O2 16.8(3) . . . . ?
O1 C1 C2 C3 76.5(3) . . . . ?
N1 C1 C2 C3 -104.0(3) . . . . ?
O2 C2 C3 C4 55.0(3) . . . . ?
C1 C2 C3 C4 177.4(2) . . . . ?
C5 N2 C4 O3 -3.4(4) . . . . ?
C5 N2 C4 C3 176.0(2) . . . . ?
C2 C3 C4 O3 56.5(3) . . . . ?
C2 C3 C4 N2 -123.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H4 O1 0.852(19) 2.21(2) 3.015(3) 157(4) 4_565
O2 H5 O1 0.873(19) 1.87(2) 2.740(3) 171(4) 4_575
N2 H7 O3 0.85(2) 2.01(2) 2.862(3) 177(5) 1_545

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_16kaw57
_database_code_depnum_ccdc_archive 'CCDC 1832194'
_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-06-18 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         'C4 H8 N2 O4'
_chemical_formula_sum            'C4 H8 N2 O4'
_chemical_formula_weight         148.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   8.0175(4)
_cell_length_b                   8.1062(4)
_cell_length_c                   9.2562(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.619(2)
_cell_angle_gamma                90
_cell_volume                     598.68(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6566
_cell_measurement_theta_min      4.80
_cell_measurement_theta_max      68.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.341
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.287
_shelx_estimated_absorpt_T_min   0.630
_shelx_estimated_absorpt_T_max   0.783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.657
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8705
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.544
_diffrn_reflns_theta_max         68.228
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             1082
_reflns_number_gt                1067
_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       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms. Those H atoms attached to nitrogen or oxygen were
 located in Fourier diff maps and assigned Uiso = 1.2xUeqiv with 
 N-H and O-H bond distances restrained to 0.85(2) angstroms.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²+0.2565P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1082
_refine_ls_number_parameters     109
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0860
_refine_ls_wR_factor_gt          0.0857
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_restrained_S_all      1.180
_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 -0.06330(11) 0.39130(12) 0.14029(10) 0.0146(3) Uani 1 1 d . . . . .
O4 O 0.57192(11) 0.38672(11) 0.36116(10) 0.0115(2) Uani 1 1 d . . . . .
O2 O 0.24054(11) 0.52418(11) 0.12747(10) 0.0125(2) Uani 1 1 d D . . . .
H5 H 0.1639(19) 0.502(2) 0.0629(16) 0.015 Uiso 1 1 d D U . . .
O3 O 0.26742(11) 0.17534(11) 0.11626(10) 0.0122(2) Uani 1 1 d D . . . .
H6 H 0.311(2) 0.0848(19) 0.1263(17) 0.015 Uiso 1 1 d D U . . .
N1 N -0.01017(14) 0.32326(14) 0.37774(13) 0.0133(3) Uani 1 1 d D . . . .
H4A H -0.1086(18) 0.286(2) 0.3825(18) 0.016 Uiso 1 1 d D U . . .
H4B H 0.062(2) 0.315(2) 0.4519(16) 0.016 Uiso 1 1 d D U . . .
N2 N 0.58674(14) 0.29397(14) 0.13190(12) 0.0128(3) Uani 1 1 d D . . . .
H7A H 0.6894(18) 0.328(2) 0.1347(18) 0.015 Uiso 1 1 d D U . . .
H7B H 0.536(2) 0.247(2) 0.0545(16) 0.015 Uiso 1 1 d D U . . .
C1 C 0.03398(15) 0.37773(15) 0.25244(14) 0.0108(3) Uani 1 1 d . . . . .
C2 C 0.21868(15) 0.42298(16) 0.24815(13) 0.0105(3) Uani 1 1 d . . . . .
H2 H 0.2572 0.4850 0.3387 0.013 Uiso 1 1 calc R U . . .
C3 C 0.32468(15) 0.26463(15) 0.24289(13) 0.0104(3) Uani 1 1 d . . . . .
H3 H 0.3097 0.1957 0.3303 0.012 Uiso 1 1 calc R U . . .
C4 C 0.50785(16) 0.31896(15) 0.24746(14) 0.0101(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2407(16) . ?
O4 C4 1.2520(16) . ?
O2 C2 1.4107(15) . ?
O2 H5 0.834(14) . ?
O3 C3 1.4153(15) . ?
O3 H6 0.815(14) . ?
N1 C1 1.3213(18) . ?
N1 H4A 0.851(14) . ?
N1 H4B 0.854(14) . ?
N2 C4 1.3106(18) . ?
N2 H7A 0.866(14) . ?
N2 H7B 0.874(13) . ?
C1 C2 1.5299(17) . ?
C2 C3 1.5428(17) . ?
C2 H2 1.0000 . ?
C3 C4 1.5298(17) . ?
C3 H3 1.0000 . ?

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 O2 H5 107.6(11) . . ?
C3 O3 H6 105.4(11) . . ?
C1 N1 H4A 119.6(11) . . ?
C1 N1 H4B 120.8(11) . . ?
H4A N1 H4B 119.3(16) . . ?
C4 N2 H7A 117.3(11) . . ?
C4 N2 H7B 121.0(11) . . ?
H7A N2 H7B 121.7(15) . . ?
O1 C1 N1 124.30(11) . . ?
O1 C1 C2 119.20(11) . . ?
N1 C1 C2 116.49(11) . . ?
O2 C2 C1 110.83(10) . . ?
O2 C2 C3 110.32(10) . . ?
C1 C2 C3 109.81(10) . . ?
O2 C2 H2 108.6 . . ?
C1 C2 H2 108.6 . . ?
C3 C2 H2 108.6 . . ?
O3 C3 C4 113.75(10) . . ?
O3 C3 C2 108.46(10) . . ?
C4 C3 C2 106.85(10) . . ?
O3 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
O4 C4 N2 124.25(12) . . ?
O4 C4 C3 117.60(11) . . ?
N2 C4 C3 118.14(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O2 19.12(16) . . . . ?
N1 C1 C2 O2 -162.00(11) . . . . ?
O1 C1 C2 C3 -103.02(13) . . . . ?
N1 C1 C2 C3 75.85(14) . . . . ?
O2 C2 C3 O3 -62.34(12) . . . . ?
C1 C2 C3 O3 60.11(13) . . . . ?
O2 C2 C3 C4 60.68(12) . . . . ?
C1 C2 C3 C4 -176.88(10) . . . . ?
O3 C3 C4 O4 -174.27(10) . . . . ?
C2 C3 C4 O4 66.08(14) . . . . ?
O3 C3 C4 N2 6.71(16) . . . . ?
C2 C3 C4 N2 -112.95(13) . . . . ?

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 H4A O2 0.851(14) 2.366(16) 3.0453(14) 137.1(15) 2_545
N1 H4B O3 0.854(14) 2.133(15) 2.9775(15) 169.9(16) 4_566
N2 H7B O4 0.874(13) 2.136(15) 2.8951(15) 145.0(14) 4_565
N2 H7A O1 0.866(14) 2.044(14) 2.9083(14) 175.8(16) 1_655
O2 H5 O1 0.834(14) 2.154(15) 2.8181(13) 136.5(15) 3_565
O3 H6 O4 0.815(14) 1.857(15) 2.6690(13) 174.1(17) 2_645

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.076

