# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_14evi05
_database_code_depnum_ccdc_archive 'CCDC 1011486'
_audit_update_record             
;
2014-07-01 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O, C2 H4 O3'
_chemical_formula_sum            'C8 H10 N2 O4'
_chemical_formula_weight         198.18

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

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

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

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

_cell_length_a                   9.6305(15)
_cell_length_b                   4.8508(9)
_cell_length_c                   19.676(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.762(8)
_cell_angle_gamma                90
_cell_volume                     899.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1286
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      26.73

_exptl_crystal_description       needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.119
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.778
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8586
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.114
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             1735
_reflns_number_gt                1256
_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 Software (Bruker, 2014)'
_computing_cell_refinement       'APEX2 Software (Bruker, 2014)'
_computing_data_reduction        'APEX2 Software (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0747P)²+0.0152P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1735
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1419
_refine_ls_wR_factor_gt          0.1270
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
O10 O 0.08189(16) 0.3602(3) 0.16996(7) 0.0179(4) Uani 1 1 d . . . . .
N10 N 0.0717(2) 0.2672(4) 0.05663(10) 0.0172(5) Uani 1 1 d . . . . .
H10A H 0.102(2) 0.307(5) 0.0169(12) 0.021 Uiso 1 1 d . U . . .
H10B H 0.007(3) 0.120(5) 0.0553(11) 0.021 Uiso 1 1 d . U . . .
N13 N 0.26431(19) 0.6639(4) 0.04915(9) 0.0179(5) Uani 1 1 d . . . . .
C11 C 0.1211(2) 0.4039(4) 0.11409(11) 0.0147(5) Uani 1 1 d . . . . .
C12 C 0.2301(2) 0.6215(4) 0.11097(11) 0.0147(5) Uani 1 1 d . . . . .
C14 C 0.3607(2) 0.8601(5) 0.04647(12) 0.0214(6) Uani 1 1 d . . . . .
H14 H 0.3863 0.8946 0.0031 0.026 Uiso 1 1 calc R U . . .
C15 C 0.4251(2) 1.0156(5) 0.10303(11) 0.0203(5) Uani 1 1 d . . . . .
H15 H 0.4926 1.1534 0.0983 0.024 Uiso 1 1 calc R U . . .
C16 C 0.3897(2) 0.9670(5) 0.16645(11) 0.0182(5) Uani 1 1 d . . . . .
H16 H 0.4331 1.0688 0.2064 0.022 Uiso 1 1 calc R U . . .
C17 C 0.2891(2) 0.7659(4) 0.17060(11) 0.0169(5) Uani 1 1 d . . . . .
H17 H 0.2614 0.7283 0.2133 0.020 Uiso 1 1 calc R U . . .
O11 O 0.91828(16) 0.9675(3) 0.19561(8) 0.0199(4) Uani 1 1 d . . . . .
H11 H 0.975(3) 1.105(5) 0.1817(12) 0.030 Uiso 1 1 d . U . . .
O12 O 0.88194(15) 0.8360(3) 0.08395(7) 0.0188(4) Uani 1 1 d . . . . .
O13 O 0.70544(19) 0.4300(4) 0.10351(9) 0.0304(5) Uani 1 1 d . . . . .
H13 H 0.730(3) 0.489(6) 0.0683(16) 0.046 Uiso 1 1 d . U . . .
C1 C 0.8598(2) 0.8161(4) 0.14239(11) 0.0159(5) Uani 1 1 d . . . . .
C2 C 0.7578(2) 0.6040(5) 0.16014(12) 0.0210(6) Uani 1 1 d . . . . .
H2A H 0.8068 0.4914 0.1998 0.025 Uiso 1 1 calc R U . . .
H2B H 0.6775 0.6993 0.1744 0.025 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O10 0.0188(9) 0.0232(9) 0.0137(8) -0.0004(6) 0.0077(7) -0.0026(7)
N10 0.0164(11) 0.0214(10) 0.0158(11) -0.0019(8) 0.0080(8) -0.0047(8)
N13 0.0154(10) 0.0222(10) 0.0179(10) -0.0010(8) 0.0076(8) -0.0033(8)
C11 0.0119(12) 0.0175(11) 0.0151(12) 0.0015(9) 0.0038(9) 0.0036(9)
C12 0.0115(12) 0.0185(11) 0.0150(11) 0.0007(9) 0.0047(9) 0.0006(9)
C14 0.0182(13) 0.0275(13) 0.0213(12) 0.0020(10) 0.0110(10) -0.0057(10)
C15 0.0157(12) 0.0216(12) 0.0253(13) -0.0026(10) 0.0084(10) -0.0030(10)
C16 0.0145(13) 0.0227(12) 0.0171(12) -0.0038(9) 0.0026(9) 0.0009(9)
C17 0.0130(12) 0.0211(12) 0.0181(12) 0.0011(9) 0.0071(10) 0.0025(9)
O11 0.0203(9) 0.0234(9) 0.0183(9) -0.0020(7) 0.0088(7) -0.0065(7)
O12 0.0203(9) 0.0217(9) 0.0164(8) -0.0014(6) 0.0084(7) -0.0029(7)
O13 0.0331(11) 0.0360(11) 0.0253(10) -0.0063(8) 0.0140(8) -0.0174(8)
C1 0.0122(12) 0.0189(11) 0.0175(12) -0.0007(10) 0.0050(9) 0.0027(9)
C2 0.0180(13) 0.0262(13) 0.0221(13) -0.0022(10) 0.0120(10) -0.0032(10)

_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
O10 C11 1.251(2) . ?
N10 C11 1.313(3) . ?
N10 H10A 0.91(2) . ?
N10 H10B 0.94(2) . ?
N13 C14 1.338(3) . ?
N13 C12 1.339(3) . ?
C11 C12 1.498(3) . ?
C12 C17 1.385(3) . ?
C14 C15 1.382(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
O11 C1 1.309(2) . ?
O11 H11 0.94(3) . ?
O12 C1 1.215(2) . ?
O13 C2 1.407(3) . ?
O13 H13 0.83(3) . ?
C1 C2 1.512(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 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
C11 N10 H10A 120.6(15) . . ?
C11 N10 H10B 121.8(14) . . ?
H10A N10 H10B 118(2) . . ?
C14 N13 C12 116.50(19) . . ?
O10 C11 N10 123.3(2) . . ?
O10 C11 C12 119.65(19) . . ?
N10 C11 C12 117.01(19) . . ?
N13 C12 C17 123.9(2) . . ?
N13 C12 C11 116.71(19) . . ?
C17 C12 C11 119.43(18) . . ?
N13 C14 C15 123.9(2) . . ?
N13 C14 H14 118.1 . . ?
C15 C14 H14 118.1 . . ?
C16 C15 C14 118.8(2) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 118.5(2) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C12 C17 C16 118.4(2) . . ?
C12 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
C1 O11 H11 110.3(15) . . ?
C2 O13 H13 110(2) . . ?
O12 C1 O11 125.6(2) . . ?
O12 C1 C2 121.33(19) . . ?
O11 C1 C2 113.02(18) . . ?
O13 C2 C1 111.73(18) . . ?
O13 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
O13 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?

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
C14 N13 C12 C17 -0.5(3) . . . . ?
C14 N13 C12 C11 179.42(18) . . . . ?
O10 C11 C12 N13 -178.01(19) . . . . ?
N10 C11 C12 N13 2.1(3) . . . . ?
O10 C11 C12 C17 2.0(3) . . . . ?
N10 C11 C12 C17 -177.98(19) . . . . ?
C12 N13 C14 C15 0.3(3) . . . . ?
N13 C14 C15 C16 0.4(3) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
N13 C12 C17 C16 0.1(3) . . . . ?
C11 C12 C17 C16 -179.89(18) . . . . ?
C15 C16 C17 C12 0.6(3) . . . . ?
O12 C1 C2 O13 4.7(3) . . . . ?
O11 C1 C2 O13 -175.23(19) . . . . ?

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
N10 H10A O12 0.91(2) 2.14(2) 2.933(2) 146(2) 3_665
N10 H10B O12 0.94(2) 1.99(2) 2.899(2) 162(2) 1_445
C14 H14 O13 0.95 2.63 3.214(3) 120.3 3_665
C15 H15 O13 0.95 2.43 3.365(3) 166.1 1_565
C17 H17 O10 0.95 2.56 3.163(3) 121.7 2
O11 H11 O10 0.94(3) 1.66(3) 2.586(2) 171(2) 1_665
O13 H13 N13 0.83(3) 2.44(3) 3.110(2) 139(3) 3_665
O13 H13 O12 0.83(3) 2.21(3) 2.680(2) 116(2) .

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.277
_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_14evi01
_database_code_depnum_ccdc_archive 'CCDC 1011487'
_audit_update_record             
;
2014-07-01 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 H6 N2 O), C2 H4 O3'
_chemical_formula_sum            'C14 H16 N4 O5'
_chemical_formula_weight         320.31

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   14.4343(12)
_cell_length_b                   12.3390(12)
_cell_length_c                   16.3675(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2915.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1942
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      30.31

_exptl_crystal_description       plate
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35298
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.489
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4439
_reflns_number_gt                3427
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       'APPEX2 Software (Bruker, 2013)'
_computing_cell_refinement       'APPEX2 Software (Bruker, 2013)'
_computing_data_reduction        'APPEX2 Software (Bruker, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0563P)²+0.9500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4439
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1140
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
O10 O 0.34220(6) 0.49362(7) 0.41197(5) 0.02015(19) Uani 1 1 d . . . . .
N10 N 0.36572(7) 0.34909(8) 0.49414(6) 0.0162(2) Uani 1 1 d . . . . .
H10A H 0.3673 0.2822 0.5006 0.019 Uiso 1 1 d R U . . .
H10B H 0.3785 0.3944 0.5346 0.019 Uiso 1 1 d R U . . .
N14 N 0.31763(7) 0.30019(8) 0.20716(6) 0.01468(19) Uani 1 1 d . . . . .
C11 C 0.34411(7) 0.39456(9) 0.42286(6) 0.0135(2) Uani 1 1 d . . . . .
C12 C 0.32186(7) 0.32025(9) 0.35325(6) 0.0115(2) Uani 1 1 d . . . . .
C13 C 0.33530(7) 0.35886(9) 0.27410(6) 0.0132(2) Uani 1 1 d . . . . .
H13 H 0.3582 0.4305 0.2673 0.016 Uiso 1 1 d R U . . .
C15 C 0.28511(8) 0.19953(9) 0.21793(7) 0.0151(2) Uani 1 1 d . . . . .
H15 H 0.2718 0.1571 0.1709 0.018 Uiso 1 1 d R U . . .
C16 C 0.26994(8) 0.15428(9) 0.29399(7) 0.0146(2) Uani 1 1 d . . . . .
H16 H 0.2470 0.0824 0.2989 0.018 Uiso 1 1 d R U . . .
C17 C 0.28884(7) 0.21552(9) 0.36297(6) 0.0132(2) Uani 1 1 d . . . . .
H17 H 0.2793 0.1863 0.4160 0.016 Uiso 1 1 d R U . . .
O20 O 0.10635(6) 0.49631(7) 0.12885(5) 0.01916(19) Uani 1 1 d . . . . .
N20 N 0.11543(7) 0.35604(8) 0.04038(6) 0.0171(2) Uani 1 1 d . . . . .
H20A H 0.1306 0.4018 0.0021 0.020 Uiso 1 1 d R U . . .
H20B H 0.1149 0.2880 0.0333 0.020 Uiso 1 1 d R U . . .
N24 N 0.06840(6) 0.29191(8) 0.32593(5) 0.01304(19) Uani 1 1 d . . . . .
C21 C 0.09996(7) 0.39828(9) 0.11413(6) 0.0128(2) Uani 1 1 d . . . . .
C22 C 0.07465(7) 0.32126(9) 0.18109(6) 0.0112(2) Uani 1 1 d . . . . .
C23 C 0.08836(7) 0.35461(9) 0.26148(6) 0.0119(2) Uani 1 1 d . . . . .
H23 H 0.1129 0.4249 0.2710 0.014 Uiso 1 1 d R U . . .
C25 C 0.03293(7) 0.19328(9) 0.31242(6) 0.0140(2) Uani 1 1 d . . . . .
H25 H 0.0191 0.1484 0.3580 0.017 Uiso 1 1 d R U . . .
C26 C 0.01545(7) 0.15413(9) 0.23451(7) 0.0140(2) Uani 1 1 d . . . . .
H26 H -0.0105 0.0841 0.2269 0.017 Uiso 1 1 d R U . . .
C27 C 0.03652(7) 0.21915(9) 0.16785(6) 0.0124(2) Uani 1 1 d . . . . .
H27 H 0.0251 0.1943 0.1139 0.015 Uiso 1 1 d R U . . .
O11 O 0.11618(6) 0.13352(6) -0.03176(5) 0.01609(17) Uani 1 1 d . . . . .
H11A H 0.0971 0.1606 -0.0850 0.024 Uiso 1 1 d R U . . .
O12 O 0.07660(6) -0.02855(7) -0.08255(5) 0.01755(18) Uani 1 1 d . . . . .
O13 O 0.13690(7) -0.13045(7) 0.05383(5) 0.02091(19) Uani 1 1 d . . . . .
H13A H 0.1544 -0.1526 0.1055 0.031 Uiso 1 1 d R U . . .
C1 C 0.10880(7) 0.02676(9) -0.02825(6) 0.0120(2) Uani 1 1 d . . . . .
C2 C 0.14578(8) -0.01762(9) 0.05124(6) 0.0141(2) Uani 1 1 d . . . . .
H2A H 0.2119 0.0024 0.0571 0.017 Uiso 1 1 d R U . . .
H2B H 0.1113 0.0148 0.0974 0.017 Uiso 1 1 d R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O10 0.0337(5) 0.0108(4) 0.0159(4) 0.0011(3) -0.0058(3) -0.0001(3)
N10 0.0252(5) 0.0101(5) 0.0132(4) 0.0016(3) -0.0046(4) 0.0004(4)
N14 0.0180(4) 0.0141(5) 0.0120(4) 0.0006(3) 0.0015(3) 0.0020(3)
C11 0.0150(5) 0.0123(5) 0.0133(5) 0.0013(4) 0.0001(4) -0.0003(4)
C12 0.0116(4) 0.0107(5) 0.0121(5) 0.0007(4) -0.0002(4) 0.0014(4)
C13 0.0154(5) 0.0106(5) 0.0135(5) 0.0020(4) 0.0010(4) 0.0004(4)
C15 0.0162(5) 0.0143(5) 0.0147(5) -0.0026(4) -0.0003(4) 0.0016(4)
C16 0.0154(5) 0.0108(5) 0.0177(5) 0.0004(4) 0.0011(4) -0.0006(4)
C17 0.0137(5) 0.0122(5) 0.0138(5) 0.0025(4) 0.0014(4) 0.0010(4)
O20 0.0323(5) 0.0091(4) 0.0161(4) -0.0012(3) 0.0032(3) -0.0020(3)
N20 0.0277(5) 0.0095(5) 0.0141(4) -0.0009(3) 0.0038(4) -0.0022(4)
N24 0.0145(4) 0.0121(5) 0.0126(4) -0.0005(3) -0.0006(3) -0.0002(3)
C21 0.0139(5) 0.0108(5) 0.0136(5) -0.0004(4) 0.0001(4) -0.0006(4)
C22 0.0122(4) 0.0095(5) 0.0118(4) -0.0015(4) 0.0004(3) 0.0003(3)
C23 0.0132(5) 0.0091(5) 0.0133(5) -0.0014(4) -0.0004(4) -0.0003(4)
C25 0.0152(5) 0.0118(5) 0.0148(5) 0.0010(4) 0.0004(4) -0.0003(4)
C26 0.0152(5) 0.0096(5) 0.0173(5) -0.0008(4) -0.0002(4) -0.0023(4)
C27 0.0128(5) 0.0115(5) 0.0129(5) -0.0023(4) -0.0007(4) -0.0004(4)
O11 0.0262(4) 0.0097(4) 0.0123(4) 0.0002(3) -0.0039(3) 0.0003(3)
O12 0.0243(4) 0.0141(4) 0.0143(4) -0.0029(3) -0.0032(3) -0.0011(3)
O13 0.0415(5) 0.0091(4) 0.0122(4) 0.0004(3) -0.0045(3) 0.0012(3)
C1 0.0136(5) 0.0112(5) 0.0111(4) -0.0013(4) 0.0011(3) 0.0008(4)
C2 0.0207(5) 0.0101(5) 0.0115(5) -0.0004(4) -0.0021(4) 0.0007(4)

_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
O10 C11 1.2355(13) . ?
N10 C11 1.3316(14) . ?
N10 H10A 0.8330 . ?
N10 H10B 0.8865 . ?
N14 C13 1.3376(14) . ?
N14 C15 1.3394(15) . ?
C11 C12 1.4972(15) . ?
C12 C17 1.3865(15) . ?
C12 C13 1.3939(14) . ?
C13 H13 0.9500 . ?
C15 C16 1.3819(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.3856(15) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
O20 C21 1.2368(13) . ?
N20 C21 1.3337(14) . ?
N20 H20A 0.8708 . ?
N20 H20B 0.8470 . ?
N24 C25 1.3386(14) . ?
N24 C23 1.3396(14) . ?
C21 C22 1.4960(15) . ?
C22 C27 1.3918(15) . ?
C22 C23 1.3927(14) . ?
C23 H23 0.9500 . ?
C25 C26 1.3867(15) . ?
C25 H25 0.9500 . ?
C26 C27 1.3880(15) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
O11 C1 1.3229(13) . ?
O11 H11A 0.9728 . ?
O12 C1 1.2130(13) . ?
O13 C2 1.3987(13) . ?
O13 H13A 0.9245 . ?
C1 C2 1.5091(15) . ?
C2 H2A 0.9900 . ?
C2 H2B 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
C11 N10 H10A 122.4 . . ?
C11 N10 H10B 116.0 . . ?
H10A N10 H10B 121.6 . . ?
C13 N14 C15 117.45(9) . . ?
O10 C11 N10 123.26(10) . . ?
O10 C11 C12 119.43(9) . . ?
N10 C11 C12 117.32(10) . . ?
C17 C12 C13 118.22(10) . . ?
C17 C12 C11 123.87(9) . . ?
C13 C12 C11 117.91(10) . . ?
N14 C13 C12 123.35(10) . . ?
N14 C13 H13 118.3 . . ?
C12 C13 H13 118.3 . . ?
N14 C15 C16 123.27(10) . . ?
N14 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C15 C16 C17 118.85(10) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C16 C17 C12 118.85(10) . . ?
C16 C17 H17 120.6 . . ?
C12 C17 H17 120.6 . . ?
C21 N20 H20A 116.1 . . ?
C21 N20 H20B 120.6 . . ?
H20A N20 H20B 123.1 . . ?
C25 N24 C23 118.50(9) . . ?
O20 C21 N20 123.10(10) . . ?
O20 C21 C22 119.79(9) . . ?
N20 C21 C22 117.11(9) . . ?
C27 C22 C23 118.09(9) . . ?
C27 C22 C21 123.89(9) . . ?
C23 C22 C21 118.01(9) . . ?
N24 C23 C22 122.87(10) . . ?
N24 C23 H23 118.5 . . ?
C22 C23 H23 118.6 . . ?
N24 C25 C26 122.56(10) . . ?
N24 C25 H25 118.7 . . ?
C26 C25 H25 118.7 . . ?
C25 C26 C27 118.79(10) . . ?
C25 C26 H26 120.6 . . ?
C27 C26 H26 120.6 . . ?
C26 C27 C22 119.17(9) . . ?
C26 C27 H27 120.4 . . ?
C22 C27 H27 120.4 . . ?
C1 O11 H11A 111.0 . . ?
C2 O13 H13A 107.3 . . ?
O12 C1 O11 124.00(10) . . ?
O12 C1 C2 124.26(10) . . ?
O11 C1 C2 111.73(9) . . ?
O13 C2 C1 110.79(9) . . ?
O13 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
O13 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?

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
O10 C11 C12 C17 -155.32(11) . . . . ?
N10 C11 C12 C17 25.05(15) . . . . ?
O10 C11 C12 C13 24.75(15) . . . . ?
N10 C11 C12 C13 -154.88(10) . . . . ?
C15 N14 C13 C12 0.22(16) . . . . ?
C17 C12 C13 N14 0.27(16) . . . . ?
C11 C12 C13 N14 -179.79(10) . . . . ?
C13 N14 C15 C16 -0.46(16) . . . . ?
N14 C15 C16 C17 0.18(17) . . . . ?
C15 C16 C17 C12 0.33(16) . . . . ?
C13 C12 C17 C16 -0.54(15) . . . . ?
C11 C12 C17 C16 179.53(10) . . . . ?
O20 C21 C22 C27 158.02(10) . . . . ?
N20 C21 C22 C27 -22.51(15) . . . . ?
O20 C21 C22 C23 -20.65(15) . . . . ?
N20 C21 C22 C23 158.82(10) . . . . ?
C25 N24 C23 C22 -0.63(16) . . . . ?
C27 C22 C23 N24 1.52(16) . . . . ?
C21 C22 C23 N24 -179.73(10) . . . . ?
C23 N24 C25 C26 -0.54(16) . . . . ?
N24 C25 C26 C27 0.77(16) . . . . ?
C25 C26 C27 C22 0.16(16) . . . . ?
C23 C22 C27 C26 -1.23(15) . . . . ?
C21 C22 C27 C26 -179.90(10) . . . . ?
O12 C1 C2 O13 -0.61(15) . . . . ?
O11 C1 C2 O13 179.71(9) . . . . ?

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
N10 H10A O13 0.83 2.07 2.8694(13) 162.1 2
N10 H10B O20 0.89 2.06 2.9433(13) 174.0 2_565
C16 H16 O10 0.95 2.51 3.2061(14) 130.5 7_655
N20 H20A O10 0.87 2.00 2.8692(13) 176.7 2_564
N20 H20B O11 0.85 2.18 2.9888(13) 158.6 .
C25 H25 O20 0.95 2.62 3.2974(14) 128.9 4_545
C26 H26 O12 0.95 2.64 3.2177(13) 119.7 5
O11 H11A N24 0.97 1.63 2.5976(12) 178.2 8_565
O13 H13A N14 0.92 1.81 2.7317(12) 176.8 7_655

_refine_diff_density_max         0.445
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_14evi04
_database_code_depnum_ccdc_archive 'CCDC 1011491'
_audit_update_record             
;
2014-07-01 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H8 N4 O2, C H3 N O'
_chemical_formula_sum            'C8 H11 N5 O3'
_chemical_formula_weight         225.22

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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'
'-x, -y, -z'

_cell_length_a                   8.2970(4)
_cell_length_b                   8.4259(4)
_cell_length_c                   8.6973(4)
_cell_angle_alpha                73.191(3)
_cell_angle_beta                 62.990(3)
_cell_angle_gamma                63.742(3)
_cell_volume                     482.84(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1674
_cell_measurement_theta_min      2.645
_cell_measurement_theta_max      23.57

_exptl_crystal_description       prism
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_F_000             236
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7808
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16916
_diffrn_reflns_av_unetI/netI     0.1367
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.645
_diffrn_reflns_theta_max         26.408
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             9155
_reflns_number_gt                5530
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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 Software (Bruker, 2014)'
_computing_cell_refinement       'APEX2 Software (Bruker, 2014)'
_computing_data_reduction        'APEX2 Software (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 Refined as a 2-component perfect twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0852P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.07(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9155
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1433
_refine_ls_R_factor_gt           0.0773
_refine_ls_wR_factor_ref         0.1931
_refine_ls_wR_factor_gt          0.1602
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
O2 O 0.7574(6) 0.5008(5) 0.4815(5) 0.0177(10) Uani 1 1 d . . . . .
O6 O 1.1803(5) 0.0396(5) 0.1504(5) 0.0174(10) Uani 1 1 d . . . . .
N1 N 0.9655(6) 0.2735(6) 0.3138(6) 0.0104(11) Uani 1 1 d . . . . .
N3 N 0.7286(6) 0.5213(6) 0.2275(6) 0.0113(11) Uani 1 1 d . . . . .
N7 N 0.9796(7) 0.2509(6) -0.1087(6) 0.0102(12) Uani 1 1 d . . . . .
H7 H 1.073(7) 0.163(7) -0.174(6) 0.012 Uiso 1 1 d . U . . .
N9 N 0.7361(7) 0.5135(6) -0.0540(6) 0.0120(11) Uani 1 1 d . . . . .
C1 C 1.0576(8) 0.1942(7) 0.4427(7) 0.0171(14) Uani 1 1 d . . . . .
H1A H 1.0998 0.2795 0.4560 0.026 Uiso 1 1 d R U . . .
H1B H 1.1705 0.0864 0.4020 0.026 Uiso 1 1 d R U . . .
H1C H 0.9647 0.1634 0.5548 0.026 Uiso 1 1 d R U . . .
C2 C 0.8125(8) 0.4373(7) 0.3471(7) 0.0114(13) Uani 1 1 d . . . . .
C3 C 0.5693(8) 0.6966(7) 0.2532(7) 0.0193(15) Uani 1 1 d . . . . .
H3A H 0.4461 0.6832 0.2855 0.029 Uiso 1 1 d R U . . .
H3B H 0.5943 0.7767 0.1453 0.029 Uiso 1 1 d R U . . .
H3C H 0.5620 0.7464 0.3460 0.029 Uiso 1 1 d R U . . .
C4 C 0.7984(7) 0.4459(7) 0.0798(7) 0.0098(13) Uani 1 1 d . . . . .
C5 C 0.9494(8) 0.2839(7) 0.0485(7) 0.0097(13) Uani 1 1 d . . . . .
C6 C 1.0447(8) 0.1841(8) 0.1679(7) 0.0130(13) Uani 1 1 d . . . . .
C8 C 0.8493(8) 0.3909(7) -0.1652(7) 0.0123(14) Uani 1 1 d . . . . .
H8 H 0.8393 0.4008 -0.2724 0.015 Uiso 1 1 d R U . . .
O10 O 0.7266(6) 0.0039(5) 0.3202(5) 0.0193(11) Uani 1 1 d . . . . .
N10 N 0.5677(7) 0.1655(7) 0.1395(6) 0.0152(12) Uani 1 1 d . . . . .
H10A H 0.659(7) 0.090(7) 0.043(7) 0.018 Uiso 1 1 d . U . . .
H10B H 0.469(8) 0.260(7) 0.117(7) 0.018 Uiso 1 1 d . U . . .
C10 C 0.5935(8) 0.1283(8) 0.2856(8) 0.0172(15) Uani 1 1 d . . . . .
H10 H 0.4996 0.2040 0.3738 0.021 Uiso 1 1 d R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.021(2) 0.015(2) 0.013(2) -0.0050(18) -0.0073(19) -0.0001(19)
O6 0.016(2) 0.013(2) 0.018(2) -0.0061(18) -0.0098(18) 0.0050(19)
N1 0.013(3) 0.009(3) 0.013(3) -0.001(2) -0.010(2) -0.001(2)
N3 0.010(3) 0.007(3) 0.009(3) -0.004(2) -0.002(2) 0.004(2)
N7 0.010(3) 0.006(3) 0.008(3) -0.004(2) -0.004(2) 0.005(2)
N9 0.015(3) 0.009(3) 0.010(3) -0.002(2) -0.006(2) -0.001(2)
C1 0.019(4) 0.019(4) 0.013(3) -0.003(3) -0.009(3) -0.002(3)
C2 0.014(3) 0.011(3) 0.007(3) -0.002(3) 0.000(3) -0.006(3)
C3 0.020(3) 0.011(3) 0.020(4) -0.005(3) -0.008(3) 0.002(3)
C4 0.008(3) 0.012(3) 0.010(3) -0.004(3) -0.002(2) -0.004(3)
C5 0.011(3) 0.014(3) 0.006(3) -0.003(2) -0.005(2) -0.002(3)
C6 0.012(3) 0.011(3) 0.015(3) -0.001(3) -0.008(3) -0.001(3)
C8 0.015(3) 0.017(4) 0.007(3) -0.003(3) -0.004(3) -0.007(3)
O10 0.016(2) 0.017(3) 0.022(3) -0.0034(19) -0.013(2) 0.0045(19)
N10 0.014(3) 0.020(3) 0.009(3) -0.008(2) -0.005(2) 0.000(2)
C10 0.014(4) 0.019(4) 0.017(4) -0.010(3) -0.001(3) -0.005(3)

_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
O2 C2 1.233(6) . ?
O6 C6 1.229(6) . ?
N1 C2 1.395(7) . ?
N1 C6 1.402(7) . ?
N1 C1 1.477(7) . ?
N3 C4 1.364(6) . ?
N3 C2 1.365(7) . ?
N3 C3 1.474(6) . ?
N7 C8 1.349(7) . ?
N7 C5 1.363(6) . ?
N7 H7 0.90(5) . ?
N9 C8 1.334(7) . ?
N9 C4 1.360(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.377(7) . ?
C5 C6 1.436(7) . ?
C8 H8 0.9500 . ?
O10 C10 1.227(7) . ?
N10 C10 1.310(7) . ?
N10 H10A 0.99(5) . ?
N10 H10B 0.91(5) . ?
C10 H10 0.9500 . ?

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 N1 C6 126.7(5) . . ?
C2 N1 C1 115.3(4) . . ?
C6 N1 C1 117.9(4) . . ?
C4 N3 C2 119.6(5) . . ?
C4 N3 C3 119.9(4) . . ?
C2 N3 C3 120.4(5) . . ?
C8 N7 C5 106.6(5) . . ?
C8 N7 H7 123(3) . . ?
C5 N7 H7 130(3) . . ?
C8 N9 C4 104.1(5) . . ?
N1 C1 H1A 109.6 . . ?
N1 C1 H1B 108.9 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.9 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 N3 122.4(5) . . ?
O2 C2 N1 119.8(5) . . ?
N3 C2 N1 117.8(5) . . ?
N3 C3 H3A 109.7 . . ?
N3 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N3 C3 H3C 109.3 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N9 C4 N3 127.2(5) . . ?
N9 C4 C5 110.8(5) . . ?
N3 C4 C5 122.0(5) . . ?
N7 C5 C4 105.8(5) . . ?
N7 C5 C6 131.7(5) . . ?
C4 C5 C6 122.5(5) . . ?
O6 C6 N1 121.8(5) . . ?
O6 C6 C5 126.8(5) . . ?
N1 C6 C5 111.4(5) . . ?
N9 C8 N7 112.6(5) . . ?
N9 C8 H8 123.7 . . ?
N7 C8 H8 123.6 . . ?
C10 N10 H10A 121(3) . . ?
C10 N10 H10B 124(3) . . ?
H10A N10 H10B 115(5) . . ?
O10 C10 N10 126.2(6) . . ?
O10 C10 H10 116.7 . . ?
N10 C10 H10 117.1 . . ?

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
C4 N3 C2 O2 178.8(5) . . . . ?
C3 N3 C2 O2 1.6(8) . . . . ?
C4 N3 C2 N1 -1.4(7) . . . . ?
C3 N3 C2 N1 -178.6(4) . . . . ?
C6 N1 C2 O2 -180.0(5) . . . . ?
C1 N1 C2 O2 -3.5(7) . . . . ?
C6 N1 C2 N3 0.2(7) . . . . ?
C1 N1 C2 N3 176.6(4) . . . . ?
C8 N9 C4 N3 -179.9(5) . . . . ?
C8 N9 C4 C5 0.4(5) . . . . ?
C2 N3 C4 N9 -178.0(5) . . . . ?
C3 N3 C4 N9 -0.8(8) . . . . ?
C2 N3 C4 C5 1.6(7) . . . . ?
C3 N3 C4 C5 178.8(5) . . . . ?
C8 N7 C5 C4 0.2(6) . . . . ?
C8 N7 C5 C6 -179.2(5) . . . . ?
N9 C4 C5 N7 -0.4(6) . . . . ?
N3 C4 C5 N7 180.0(5) . . . . ?
N9 C4 C5 C6 179.1(5) . . . . ?
N3 C4 C5 C6 -0.6(8) . . . . ?
C2 N1 C6 O6 180.0(5) . . . . ?
C1 N1 C6 O6 3.6(7) . . . . ?
C2 N1 C6 C5 0.8(7) . . . . ?
C1 N1 C6 C5 -175.6(5) . . . . ?
N7 C5 C6 O6 -0.4(10) . . . . ?
C4 C5 C6 O6 -179.7(5) . . . . ?
N7 C5 C6 N1 178.7(5) . . . . ?
C4 C5 C6 N1 -0.6(7) . . . . ?
C4 N9 C8 N7 -0.3(6) . . . . ?
C5 N7 C8 N9 0.1(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
N7 H7 O10 0.90(5) 1.84(5) 2.741(6) 175(5) 2_755
N10 H10A O6 0.99(5) 1.88(5) 2.872(6) 176(4) 2_755
N10 H10B N9 0.91(5) 2.05(5) 2.954(7) 175(5) 2_665
C3 H3A O2 0.98 2.60 3.395(7) 138.5 2_666
C8 H8 O2 0.95 2.35 3.277(7) 164.9 1_554
C10 H10 O2 0.95 2.65 3.550(7) 159.2 2_666

_refine_diff_density_max         0.634
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.173


####################################################################### 
# 
# 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_14evi02
_database_code_depnum_ccdc_archive 'CCDC 1011490'
_audit_update_record             
;
2014-07-01 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H10 N4 O2, 2(C2 H4 O3)'
_chemical_formula_sum            'C12 H18 N4 O8'
_chemical_formula_weight         346.30

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

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

_cell_length_a                   16.8076(15)
_cell_length_b                   6.3120(6)
_cell_length_c                   13.8556(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1469.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1977
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      29.01

_exptl_crystal_description       needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16112
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.905
_diffrn_reflns_theta_max         30.532
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2428
_reflns_number_gt                1774
_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 Software (Bruker, 2013)'
_computing_cell_refinement       'APEX2 Software (Bruker, 2013)'
_computing_data_reduction        'APEX2 Software (Bruker, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²+0.5828P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0019(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2428
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.0916
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.07801(8) 0.2500 0.33963(9) 0.0162(3) Uani 1 2 d S T P . .
O6 O 0.24401(7) 0.2500 0.07746(9) 0.0154(3) Uani 1 2 d S T P . .
N1 N 0.15962(8) 0.2500 0.20771(11) 0.0120(3) Uani 1 2 d S T P . .
N3 N 0.01956(8) 0.2500 0.19218(11) 0.0114(3) Uani 1 2 d S T P . .
N7 N 0.09180(9) 0.2500 -0.04554(10) 0.0112(3) Uani 1 2 d S T P . .
N9 N -0.02755(8) 0.2500 0.02476(11) 0.0114(3) Uani 1 2 d S T P . .
C1 C 0.23007(11) 0.2500 0.27035(14) 0.0193(4) Uani 1 2 d S T P . .
H1A H 0.2643 0.1272 0.2548 0.023 Uiso 1 1 d R U . . .
H1B H 0.2168 0.2500 0.3325 0.023 Uiso 1 2 d R U P . .
C2 C 0.08500(10) 0.2500 0.25168(13) 0.0119(3) Uani 1 2 d S T P . .
C3 C -0.05949(10) 0.2500 0.23689(13) 0.0157(4) Uani 1 2 d S T P . .
H3A H -0.0678 0.1222 0.2772 0.019 Uiso 1 1 d R U . . .
H3B H -0.0985 0.2500 0.1845 0.019 Uiso 1 2 d R U P . .
C4 C 0.03023(10) 0.2500 0.09393(12) 0.0102(3) Uani 1 2 d S T P . .
C5 C 0.10429(10) 0.2500 0.05299(12) 0.0103(3) Uani 1 2 d S T P . .
C6 C 0.17578(10) 0.2500 0.10827(13) 0.0114(3) Uani 1 2 d S T P . .
C7 C 0.15349(12) 0.2500 -0.12032(13) 0.0163(4) Uani 1 2 d S T P . .
H7A H 0.1270 0.2500 -0.1831 0.020 Uiso 1 2 d R U P . .
H7B H 0.1872 0.1294 -0.1143 0.020 Uiso 1 1 d R U . . .
C8 C 0.01292(10) 0.2500 -0.05872(13) 0.0118(3) Uani 1 2 d S T P . .
H8 H -0.0114 0.2500 -0.1243 0.014 Uiso 1 2 d R U P . .
O11 O 0.15119(7) 0.7500 0.32668(10) 0.0171(3) Uani 1 2 d S T P . .
H11 H 0.1598 0.7500 0.2620 0.026 Uiso 1 2 d R U P . .
O12 O 0.02106(8) 0.7500 0.28751(10) 0.0169(3) Uani 1 2 d S T P . .
O13 O -0.02179(7) 0.7500 0.47193(10) 0.0180(3) Uani 1 2 d S T P . .
H13 H -0.0323 0.7500 0.5320 0.027 Uiso 1 2 d R U P . .
C11 C 0.07385(10) 0.7500 0.34699(13) 0.0123(3) Uani 1 2 d S T P . .
C12 C 0.06086(10) 0.7500 0.45439(12) 0.0136(4) Uani 1 2 d S T P . .
H12A H 0.0877 0.6227 0.4814 0.016 Uiso 1 1 d R U . . .
O21 O 0.18306(7) 0.7500 -0.02395(9) 0.0156(3) Uani 1 2 d S T P . .
H21 H 0.1219 0.7500 -0.0185 0.023 Uiso 1 2 d R U P . .
O22 O 0.17441(8) 0.7500 0.13638(10) 0.0170(3) Uani 1 2 d S T P . .
O23 O 0.33908(8) 0.7500 0.14899(10) 0.0215(3) Uani 1 2 d S T P . .
H23 H 0.3900 0.7500 0.1391 0.032 Uiso 1 2 d R U P . .
C21 C 0.21458(10) 0.7500 0.06310(12) 0.0115(3) Uani 1 2 d S T P . .
C22 C 0.30369(10) 0.7500 0.05736(12) 0.0150(4) Uani 1 2 d S T P . .
H22A H 0.3181 0.6190 0.0198 0.018 Uiso 1 1 d R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0185(6) 0.0217(7) 0.0084(6) 0.000 0.0006(5) 0.000
O6 0.0098(6) 0.0204(7) 0.0159(6) 0.000 0.0005(5) 0.000
N1 0.0090(6) 0.0165(8) 0.0106(7) 0.000 -0.0021(5) 0.000
N3 0.0093(6) 0.0146(8) 0.0103(7) 0.000 0.0005(5) 0.000
N7 0.0140(7) 0.0117(7) 0.0078(6) 0.000 0.0000(5) 0.000
N9 0.0111(7) 0.0113(7) 0.0119(7) 0.000 -0.0020(5) 0.000
C1 0.0118(8) 0.0317(11) 0.0143(9) 0.000 -0.0068(7) 0.000
C2 0.0129(8) 0.0120(8) 0.0108(8) 0.000 -0.0011(6) 0.000
C3 0.0095(8) 0.0225(10) 0.0151(8) 0.000 0.0034(6) 0.000
C4 0.0100(7) 0.0090(8) 0.0117(8) 0.000 -0.0010(6) 0.000
C5 0.0108(7) 0.0117(8) 0.0085(7) 0.000 0.0002(6) 0.000
C6 0.0127(8) 0.0099(8) 0.0114(8) 0.000 0.0011(6) 0.000
C7 0.0196(9) 0.0177(9) 0.0117(8) 0.000 0.0044(7) 0.000
C8 0.0136(8) 0.0111(8) 0.0108(8) 0.000 -0.0027(6) 0.000
O11 0.0121(6) 0.0253(8) 0.0138(6) 0.000 0.0019(5) 0.000
O12 0.0156(6) 0.0214(7) 0.0136(6) 0.000 -0.0021(5) 0.000
O13 0.0129(6) 0.0287(8) 0.0126(6) 0.000 0.0027(5) 0.000
C11 0.0123(7) 0.0112(8) 0.0132(8) 0.000 0.0006(6) 0.000
C12 0.0118(8) 0.0177(9) 0.0112(8) 0.000 -0.0002(6) 0.000
O21 0.0112(6) 0.0240(7) 0.0115(6) 0.000 0.0001(5) 0.000
O22 0.0162(6) 0.0219(7) 0.0130(6) 0.000 0.0040(5) 0.000
O23 0.0136(6) 0.0375(9) 0.0133(7) 0.000 -0.0037(5) 0.000
C21 0.0122(7) 0.0108(8) 0.0114(8) 0.000 0.0006(6) 0.000
C22 0.0109(8) 0.0230(10) 0.0110(8) 0.000 -0.0005(6) 0.000

_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
O2 C2 1.224(2) . ?
O6 C6 1.224(2) . ?
N1 C2 1.394(2) . ?
N1 C6 1.404(2) . ?
N1 C1 1.468(2) . ?
N3 C4 1.373(2) . ?
N3 C2 1.375(2) . ?
N3 C3 1.466(2) . ?
N7 C8 1.338(2) . ?
N7 C5 1.381(2) . ?
N7 C7 1.466(2) . ?
N9 C8 1.342(2) . ?
N9 C4 1.364(2) . ?
C1 H1A 0.9894 . ?
C1 H1B 0.8890 . ?
C3 H3A 0.9914 . ?
C3 H3B 0.9782 . ?
C4 C5 1.368(2) . ?
C5 C6 1.425(2) . ?
C7 H7A 0.9770 . ?
C7 H7B 0.9521 . ?
C8 H8 0.9960 . ?
O11 C11 1.330(2) . ?
O11 H11 0.9077 . ?
O12 C11 1.211(2) . ?
O13 C12 1.410(2) . ?
O13 H13 0.8512 . ?
C11 C12 1.504(2) . ?
C12 H12A 0.9940 . ?
O21 C21 1.317(2) . ?
O21 H21 1.0304 . ?
O22 C21 1.219(2) . ?
O23 C22 1.402(2) . ?
O23 H23 0.8661 . ?
C21 C22 1.500(2) . ?
C22 H22A 1.0067 . ?

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 N1 C6 127.06(14) . . ?
C2 N1 C1 117.85(15) . . ?
C6 N1 C1 115.09(14) . . ?
C4 N3 C2 119.35(14) . . ?
C4 N3 C3 122.50(14) . . ?
C2 N3 C3 118.15(15) . . ?
C8 N7 C5 106.58(14) . . ?
C8 N7 C7 127.18(15) . . ?
C5 N7 C7 126.24(15) . . ?
C8 N9 C4 104.16(14) . . ?
N1 C1 H1A 109.9 . . ?
N1 C1 H1B 111.7 . . ?
H1A C1 H1B 111.0 . . ?
O2 C2 N3 121.35(16) . . ?
O2 C2 N1 121.41(16) . . ?
N3 C2 N1 117.24(15) . . ?
N3 C3 H3A 111.5 . . ?
N3 C3 H3B 107.1 . . ?
H3A C3 H3B 108.9 . . ?
N9 C4 C5 110.88(15) . . ?
N9 C4 N3 127.12(15) . . ?
C5 C4 N3 122.00(15) . . ?
C4 C5 N7 105.76(15) . . ?
C4 C5 C6 122.98(15) . . ?
N7 C5 C6 131.25(16) . . ?
O6 C6 N1 121.57(16) . . ?
O6 C6 C5 127.07(16) . . ?
N1 C6 C5 111.36(14) . . ?
N7 C7 H7A 107.9 . . ?
N7 C7 H7B 111.0 . . ?
H7A C7 H7B 110.4 . . ?
N7 C8 N9 112.61(15) . . ?
N7 C8 H8 122.1 . . ?
N9 C8 H8 125.3 . . ?
C11 O11 H11 111.4 . . ?
C12 O13 H13 111.9 . . ?
O12 C11 O11 124.90(16) . . ?
O12 C11 C12 124.54(16) . . ?
O11 C11 C12 110.56(15) . . ?
O13 C12 C11 108.27(14) . . ?
O13 C12 H12A 112.4 . . ?
C11 C12 H12A 107.9 . . ?
C21 O21 H21 109.5 . . ?
C22 O23 H23 106.0 . . ?
O22 C21 O21 122.66(16) . . ?
O22 C21 C22 126.66(16) . . ?
O21 C21 C22 110.67(15) . . ?
O23 C22 C21 112.06(14) . . ?
O23 C22 H22A 111.4 . . ?
C21 C22 H22A 105.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N3 C2 O2 180.000(0) . . . . ?
C3 N3 C2 O2 0.000(0) . . . . ?
C4 N3 C2 N1 0.000(0) . . . . ?
C3 N3 C2 N1 180.0 . . . . ?
C6 N1 C2 O2 180.000(0) . . . . ?
C1 N1 C2 O2 0.000(0) . . . . ?
C6 N1 C2 N3 0.000(0) . . . . ?
C1 N1 C2 N3 180.0 . . . . ?
C8 N9 C4 C5 0.0 . . . . ?
C8 N9 C4 N3 180.0 . . . . ?
C2 N3 C4 N9 180.0 . . . . ?
C3 N3 C4 N9 0.0 . . . . ?
C2 N3 C4 C5 0.0 . . . . ?
C3 N3 C4 C5 180.0 . . . . ?
N9 C4 C5 N7 0.0 . . . . ?
N3 C4 C5 N7 180.0 . . . . ?
N9 C4 C5 C6 180.0 . . . . ?
N3 C4 C5 C6 0.0 . . . . ?
C8 N7 C5 C4 0.0 . . . . ?
C7 N7 C5 C4 180.0 . . . . ?
C8 N7 C5 C6 180.0 . . . . ?
C7 N7 C5 C6 0.0 . . . . ?
C2 N1 C6 O6 180.0 . . . . ?
C1 N1 C6 O6 0.0 . . . . ?
C2 N1 C6 C5 0.0 . . . . ?
C1 N1 C6 C5 180.0 . . . . ?
C4 C5 C6 O6 180.0 . . . . ?
N7 C5 C6 O6 0.0 . . . . ?
C4 C5 C6 N1 0.0 . . . . ?
N7 C5 C6 N1 180.0 . . . . ?
C5 N7 C8 N9 0.0 . . . . ?
C7 N7 C8 N9 180.0 . . . . ?
C4 N9 C8 N7 0.0 . . . . ?
O12 C11 C12 O13 0.000(0) . . . . ?
O11 C11 C12 O13 180.000(0) . . . . ?
O22 C21 C22 O23 0.0 . . . . ?
O21 C21 C22 O23 180.0 . . . . ?

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
O11 H11 O22 0.91 1.76 2.6654(19) 178.8 .
O13 H13 O2 0.85 1.94 2.7767(19) 168.6 5_566
O21 H21 N9 1.03 1.59 2.6137(19) 172.7 5_565
O23 H23 O12 0.87 2.43 3.1826(19) 146.1 6_656
O23 H23 O13 0.87 2.14 2.8767(19) 143.0 6_656
C1 H1B O21 0.89 2.61 3.202(2) 125.2 2_565
C3 H3B O21 0.98 2.64 3.608(2) 170.5 5_565
C7 H7A O23 0.98 2.40 3.199(2) 139.2 2_564
C8 H8 O12 1.00 2.27 3.221(2) 159.9 5_565

_refine_diff_density_max         0.380
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.075
####################################################################### 
# 
# 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_19ac01
_database_code_depnum_ccdc_archive 'CCDC 1938426'
loop_
_audit_author_name
_audit_author_address
'Alfonso Castineiras'
;University of Santiago de Compostela
Spain
;
_audit_update_record             
;
2019-07-04 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 H4 O3, C2 H3 O3, H4 N'
_chemical_formula_sum            'C4 H11 N O6'
_chemical_formula_weight         169.14

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                   3.81770(10)
_cell_length_b                   18.7165(7)
_cell_length_c                   10.7428(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.012(2)
_cell_angle_gamma                90
_cell_volume                     725.74(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1964
_cell_measurement_theta_min      4.725
_cell_measurement_theta_max      74.46

_exptl_crystal_description       plate
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.303
_shelx_estimated_absorpt_T_min   0.829
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III-14'
_diffrn_measurement_method       'omega and phi'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15809
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.725
_diffrn_reflns_theta_max         74.522
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1487
_reflns_number_gt                1391
_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       'APEX3 Software (Bruker, 2018)'
_computing_cell_refinement       'APEX3 Software (Bruker, 2018)'
_computing_data_reduction        'APEX3 Software (Bruker, 2018)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²+0.3407P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1487
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0748
_refine_ls_wR_factor_gt          0.0735
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
O21 O 0.2256(2) -0.03870(4) 0.32859(8) 0.0186(2) Uani 1 1 d . . . . .
H21 H 0.1217 -0.0785 0.2795 0.028 Uiso 1 1 d R U . . .
O22 O 0.2938(2) 0.00705(4) 0.14431(8) 0.0159(2) Uani 1 1 d . . . . .
O23 O 0.6402(2) 0.12470(4) 0.27654(8) 0.0159(2) Uani 1 1 d . . . . .
H23 H 0.5385 0.1630 0.2802 0.024 Uiso 1 1 d R U . . .
C3 C 0.3320(3) 0.01070(6) 0.26130(11) 0.0130(2) Uani 1 1 d . . . . .
C4 C 0.5099(3) 0.07345(6) 0.34735(11) 0.0143(2) Uani 1 1 d . . . . .
H4A H 0.3267 0.0960 0.3823 0.017 Uiso 1 1 calc R U . . .
H4B H 0.7194 0.0562 0.4230 0.017 Uiso 1 1 calc R U . . .
O11 O 0.0663(2) 0.35281(4) 0.30605(8) 0.0154(2) Uani 1 1 d . . . . .
O12 O 0.2975(2) 0.24333(4) 0.31943(8) 0.0163(2) Uani 1 1 d . . . . .
O13 O 0.2221(2) 0.23897(4) 0.06190(8) 0.0156(2) Uani 1 1 d . . . . .
H13 H 0.2242 0.2468 -0.0138 0.023 Uiso 1 1 d R U . . .
C1 C 0.1636(3) 0.29788(6) 0.25508(11) 0.0120(2) Uani 1 1 d . . . . .
C2 C 0.1126(3) 0.30289(6) 0.10907(10) 0.0131(2) Uani 1 1 d . . . . .
H2A H -0.1510 0.3127 0.0596 0.016 Uiso 1 1 calc R U . . .
H2B H 0.2616 0.3432 0.0937 0.016 Uiso 1 1 calc R U . . .
N1 N 0.7169(3) 0.11751(5) 0.02493(9) 0.0148(2) Uani 1 1 d . . . . .
H1 H 0.8135 0.0766 0.0033 0.018 Uiso 1 1 d R U . . .
H2 H 0.8687 0.1557 0.0331 0.018 Uiso 1 1 d R U . . .
H3 H 0.6650 0.1130 0.1040 0.018 Uiso 1 1 d R U . . .
H4 H 0.5006 0.1279 -0.0418 0.018 Uiso 1 1 d R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O21 0.0297(5) 0.0132(4) 0.0140(4) -0.0008(3) 0.0088(3) -0.0069(3)
O22 0.0223(4) 0.0141(4) 0.0123(4) -0.0004(3) 0.0068(3) 0.0007(3)
O23 0.0238(4) 0.0087(4) 0.0188(4) 0.0007(3) 0.0121(3) 0.0002(3)
C3 0.0135(5) 0.0115(5) 0.0145(5) 0.0007(4) 0.0055(4) 0.0022(4)
C4 0.0194(6) 0.0122(5) 0.0130(5) 0.0000(4) 0.0078(4) -0.0018(4)
O11 0.0217(4) 0.0122(4) 0.0133(4) -0.0006(3) 0.0074(3) 0.0034(3)
O12 0.0259(4) 0.0119(4) 0.0134(4) 0.0021(3) 0.0094(3) 0.0037(3)
O13 0.0259(4) 0.0121(4) 0.0120(4) -0.0009(3) 0.0103(3) 0.0011(3)
C1 0.0136(5) 0.0104(5) 0.0136(5) -0.0006(4) 0.0064(4) -0.0014(4)
C2 0.0173(5) 0.0112(5) 0.0120(5) -0.0003(4) 0.0062(4) 0.0011(4)
N1 0.0190(5) 0.0121(5) 0.0155(5) 0.0006(4) 0.0085(4) 0.0014(4)

_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
O21 C3 1.3166(14) . ?
O21 H21 0.9238 . ?
O22 C3 1.2192(14) . ?
O23 C4 1.4116(13) . ?
O23 H23 0.8225 . ?
C3 C4 1.5120(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
O11 C1 1.2756(14) . ?
O12 C1 1.2455(14) . ?
O13 C2 1.4144(13) . ?
O13 H13 0.8291 . ?
C1 C2 1.5192(14) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N1 H1 0.9126 . ?
N1 H2 0.9066 . ?
N1 H3 0.9372 . ?
N1 H4 0.9208 . ?

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
C3 O21 H21 113.9 . . ?
C4 O23 H23 108.2 . . ?
O22 C3 O21 124.89(10) . . ?
O22 C3 C4 123.55(10) . . ?
O21 C3 C4 111.55(9) . . ?
O23 C4 C3 111.43(9) . . ?
O23 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
O23 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C2 O13 H13 107.5 . . ?
O12 C1 O11 123.14(10) . . ?
O12 C1 C2 121.00(10) . . ?
O11 C1 C2 115.86(9) . . ?
O13 C2 C1 111.36(9) . . ?
O13 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
O13 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
H1 N1 H2 112.9 . . ?
H1 N1 H3 112.2 . . ?
H2 N1 H3 107.4 . . ?
H1 N1 H4 108.3 . . ?
H2 N1 H4 107.0 . . ?
H3 N1 H4 108.9 . . ?

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
O22 C3 C4 O23 -2.89(15) . . . . ?
O21 C3 C4 O23 177.07(9) . . . . ?
O12 C1 C2 O13 2.03(14) . . . . ?
O11 C1 C2 O13 -178.95(9) . . . . ?

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
O21 H21 O11 0.92 1.61 2.5312(11) 179.0 2_545
O23 H23 O12 0.82 1.88 2.6921(11) 168.7 .
C4 H4B O21 0.99 2.63 3.3574(14) 130.6 3_656
O13 H13 O11 0.83 2.61 3.1296(11) 121.9 4_565
O13 H13 O12 0.83 1.91 2.7326(11) 171.3 4_565
N1 H1 O22 0.91 2.35 2.9882(12) 126.5 1_655
N1 H1 O22 0.91 2.17 2.9485(12) 142.7 3_655
N1 H2 O13 0.91 2.02 2.9233(12) 176.7 1_655
N1 H3 O22 0.94 2.56 3.1427(12) 121.0 .
N1 H3 O23 0.94 1.90 2.8152(12) 165.3 .
N1 H4 O11 0.92 1.95 2.8639(13) 174.8 4_565

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-3

_shelx_res_file                  
;
TITL 19ac01 = 19ag05 =19gsg012b = GLYCOLLIC in P21/c, Cu, 1/04/2019
CELL  1.54178    3.8177   18.7165   10.7428    90.000   109.012    90.000
ZERR  4          0.0001    0.0007    0.0004     0.000     0.002     0.000
LATT   1
SYMM             - X ,    0.50000 + Y ,    0.50000 - Z
SFAC     C    H   N   O
UNIT    16   44   4  24
EQIV $1 -x, y-1/2, -z+1/2
EQIV $2 -x+1, -y, -z+1
EQIV $3 x, -y+1/2, z-1/2
EQIV $4 x+1, y, z
EQIV $5 -x+1, -y, -z
BOND $H
CONF
HTAB O21 O11_$1
HTAB O23 O12
HTAB C4 O21_$2
HTAB O13 O11_$3
HTAB O13 O12_$3
HTAB N1 O22_$4
HTAB N1 O22_$5
HTAB N1 O13_$4
HTAB N1 O22
HTAB N1 O23
HTAB N1 O11_$3
MERG 2
FMAP 2
PLAN -10
L.S. 10
MPLA 4 C1 C2 O11 O12 O13
MPLA 4 C3 C4 O21 O22 O23
ACTA
SIZE   0.15  0.11  0.08
TEMP  -173
WGHT    0.031400    0.340700
FVAR       0.30171
O21   4    0.225602   -0.038701    0.328586    11.00000    0.02969    0.01324 =
         0.01403   -0.00078    0.00876   -0.00688
AFIX   3
H21   2    0.121702   -0.078481    0.279506    11.00000   -1.50000
AFIX   0
O22   4    0.293841    0.007053    0.144307    11.00000    0.02232    0.01406 =
         0.01226   -0.00041    0.00681    0.00068
O23   4    0.640235    0.124695    0.276539    11.00000    0.02382    0.00871 =
         0.01883    0.00066    0.01212    0.00017
AFIX   3
H23   2    0.538475    0.163005    0.280189    11.00000   -1.50000
AFIX   0
C3    1    0.331959    0.010701    0.261302    11.00000    0.01355    0.01148 =
         0.01453    0.00071    0.00548    0.00217
C4    1    0.509930    0.073449    0.347352    11.00000    0.01941    0.01224 =
         0.01295    0.00003    0.00781   -0.00181
AFIX  23
H4A   2    0.326729    0.096020    0.382333    11.00000   -1.20000
H4B   2    0.719370    0.056248    0.423004    11.00000   -1.20000
AFIX   0
O11   4    0.066321    0.352808    0.306049    11.00000    0.02173    0.01221 =
         0.01334   -0.00056    0.00737    0.00343
O12   4    0.297527    0.243335    0.319426    11.00000    0.02594    0.01188 =
         0.01336    0.00215    0.00937    0.00368
O13   4    0.222066    0.238970    0.061903    11.00000    0.02589    0.01213 =
         0.01195   -0.00090    0.01032    0.00105
AFIX   3
H13   2    0.224216    0.246760   -0.013817    11.00000   -1.50000
AFIX   0
C1    1    0.163555    0.297875    0.255076    11.00000    0.01357    0.01039 =
         0.01363   -0.00057    0.00641   -0.00145
C2    1    0.112566    0.302887    0.109067    11.00000    0.01732    0.01117 =
         0.01199   -0.00032    0.00623    0.00109
AFIX  23
H2A   2   -0.151028    0.312663    0.059610    11.00000   -1.20000
H2B   2    0.261607    0.343161    0.093739    11.00000   -1.20000
AFIX   0
N1    3    0.716926    0.117507    0.024933    11.00000    0.01896    0.01211 =
         0.01551    0.00059    0.00850    0.00136
AFIX   3
H1    2    0.813496    0.076567    0.003303    11.00000   -1.20000
H2    2    0.868686    0.155727    0.033113    11.00000   -1.20000
H3    2    0.664996    0.113047    0.104043    11.00000   -1.20000
H4    2    0.500606    0.127897   -0.041787    11.00000   -1.20000
AFIX   0
HKLF 4 1 -1.0000  0.0000  0.0000  0.0000 -1.0000  0.0000  1.0000  0.0000  1.0000

REM  19ac01 = 19ag05 =19gsg012b = GLYCOLLIC in P21/c, Cu, 1/04/2019
REM R1 =  0.0284 for    1391 Fo > 4sig(Fo)  and  0.0302 for all    1487 data
REM    100 parameters refined using      0 restraints

END

WGHT      0.0314      0.3401

REM Highest difference peak  0.328,  deepest hole -0.218,  1-sigma level  0.046
Q1    1   0.1438  0.2002 -0.3138  11.00000  0.05    0.33
Q2    1   0.3859  0.0480  0.3032  11.00000  0.05    0.22
Q3    1   0.4276  0.0807  0.3995  11.00000  0.05    0.17
Q4    1   0.3547  0.1548 -0.3584  11.00000  0.05    0.15
Q5    1   0.3703  0.2440  0.4064  11.00000  0.05    0.15
Q6    1   0.5668  0.1062  0.1936  11.00000  0.05    0.14
Q7    1   0.1183  0.1498 -0.1135  11.00000  0.05    0.13
Q8    1   0.3975  0.0006  0.1980  11.00000  0.05    0.13
Q9    1   0.2242  0.0120  0.1878  11.00000  0.05    0.13
Q10   1   0.1126  0.1624 -0.2203  11.00000  0.05    0.13
;
_shelx_res_checksum              94122
####################################################################### 
# 
# 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_13co01
_database_code_depnum_ccdc_archive 'CCDC 1011488'
_audit_update_record             
;
2014-07-01 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O, C2 H4 O3'
_chemical_formula_sum            'C8 H10 N2 O4'
_chemical_formula_weight         198.18

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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'
'-x, -y, -z'

_cell_length_a                   3.7260(3)
_cell_length_b                   10.5594(9)
_cell_length_c                   10.9879(9)
_cell_angle_alpha                84.170(6)
_cell_angle_beta                 87.921(5)
_cell_angle_gamma                85.492(6)
_cell_volume                     428.57(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1967
_cell_measurement_theta_min      2.555
_cell_measurement_theta_max      26.35

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_F_000             208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8416
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12421
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.864
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1749
_reflns_number_gt                1546
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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 Software (Bruker, 2013)'
_computing_cell_refinement       'APEX2 Software (Bruker, 2013)'
_computing_data_reduction        'APEX2 Software (Bruker, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0599P)²+0.1610P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1749
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
O10 O 0.5955(3) 0.65294(9) 0.42187(8) 0.0188(2) Uani 1 1 d . . . . .
N10 N 0.8065(3) 0.46073(11) 0.36634(10) 0.0181(3) Uani 1 1 d . . . . .
H10A H 0.691(4) 0.4256(15) 0.4337(16) 0.022 Uiso 1 1 d . U . . .
H10B H 0.946(4) 0.4088(16) 0.3204(15) 0.022 Uiso 1 1 d . U . . .
N15 N 1.2254(3) 0.78472(10) 0.02717(9) 0.0166(3) Uani 1 1 d . . . . .
C11 C 0.7710(3) 0.58653(12) 0.34992(11) 0.0146(3) Uani 1 1 d . . . . .
C12 C 0.9424(3) 0.65265(12) 0.23640(11) 0.0147(3) Uani 1 1 d . . . . .
C13 C 1.0992(3) 0.58721(12) 0.14149(11) 0.0162(3) Uani 1 1 d . . . . .
H13 H 1.109(4) 0.4962(16) 0.1418(14) 0.019 Uiso 1 1 d . U . . .
C14 C 1.2340(3) 0.65743(12) 0.03885(11) 0.0167(3) Uani 1 1 d . . . . .
H14 H 1.347(4) 0.6158(15) -0.0288(15) 0.020 Uiso 1 1 d . U . . .
C16 C 1.0786(4) 0.84703(13) 0.11899(12) 0.0178(3) Uani 1 1 d . . . . .
H16 H 1.078(4) 0.9374(16) 0.1095(15) 0.021 Uiso 1 1 d . U . . .
C17 C 0.9327(3) 0.78471(12) 0.22442(11) 0.0167(3) Uani 1 1 d . . . . .
H17 H 0.822(4) 0.8355(15) 0.2851(15) 0.020 Uiso 1 1 d . U . . .
O11 O 0.5602(3) 0.09896(9) 0.18080(9) 0.0199(2) Uani 1 1 d . . . . .
H11 H 0.622(5) 0.1456(17) 0.1074(17) 0.030 Uiso 1 1 d . U . . .
O12 O 0.2696(3) 0.28401(9) 0.22239(8) 0.0220(3) Uani 1 1 d . . . . .
O13 O 0.0639(3) 0.17339(10) 0.45305(9) 0.0285(3) Uani 1 1 d . . . . .
H13A H 0.190(6) 0.224(2) 0.4851(18) 0.043 Uiso 1 1 d . U . . .
C1 C 0.3673(3) 0.17321(12) 0.25185(11) 0.0161(3) Uani 1 1 d . . . . .
C2 C 0.2881(4) 0.10209(13) 0.37550(12) 0.0202(3) Uani 1 1 d . . . . .
H2A H 0.170(4) 0.0249(16) 0.3599(15) 0.024 Uiso 1 1 d . U . . .
H2B H 0.527(5) 0.0740(15) 0.4085(15) 0.024 Uiso 1 1 d . U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O10 0.0247(5) 0.0213(5) 0.0097(4) -0.0024(3) 0.0051(4) 0.0005(4)
N10 0.0237(6) 0.0204(6) 0.0100(5) -0.0021(4) 0.0065(4) -0.0026(5)
N15 0.0174(6) 0.0224(6) 0.0099(5) -0.0016(4) 0.0017(4) -0.0013(4)
C11 0.0147(6) 0.0219(6) 0.0075(6) -0.0021(5) -0.0007(4) -0.0015(5)
C12 0.0136(6) 0.0225(7) 0.0081(6) -0.0017(5) -0.0002(4) -0.0015(5)
C13 0.0187(6) 0.0179(6) 0.0120(6) -0.0022(5) 0.0008(5) -0.0008(5)
C14 0.0184(6) 0.0225(7) 0.0091(6) -0.0035(5) 0.0021(5) -0.0001(5)
C16 0.0211(7) 0.0191(7) 0.0130(6) -0.0017(5) 0.0013(5) -0.0018(5)
C17 0.0190(6) 0.0214(7) 0.0099(6) -0.0040(5) 0.0013(5) -0.0006(5)
O11 0.0273(5) 0.0189(5) 0.0122(5) 0.0001(4) 0.0069(4) 0.0007(4)
O12 0.0316(6) 0.0190(5) 0.0149(5) -0.0021(4) 0.0057(4) 0.0001(4)
O13 0.0425(7) 0.0306(6) 0.0147(5) -0.0103(4) 0.0116(4) -0.0142(5)
C1 0.0172(6) 0.0200(6) 0.0117(6) -0.0037(5) 0.0006(5) -0.0037(5)
C2 0.0216(7) 0.0269(7) 0.0118(6) 0.0000(5) 0.0029(5) -0.0035(5)

_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
O10 C11 1.2439(15) . ?
N10 C11 1.3190(17) . ?
N10 H10A 0.904(18) . ?
N10 H10B 0.904(18) . ?
N15 C14 1.3351(17) . ?
N15 C16 1.3373(17) . ?
C11 C12 1.5122(17) . ?
C12 C17 1.3851(18) . ?
C12 C13 1.3947(17) . ?
C13 C14 1.3862(18) . ?
C13 H13 0.959(16) . ?
C14 H14 0.969(16) . ?
C16 C17 1.3879(18) . ?
C16 H16 0.949(16) . ?
C17 H17 0.959(16) . ?
O11 C1 1.3176(16) . ?
O11 H11 0.933(19) . ?
O12 C1 1.2127(16) . ?
O13 C2 1.4037(17) . ?
O13 H13A 0.85(2) . ?
C1 C2 1.5151(17) . ?
C2 H2A 0.989(17) . ?
C2 H2B 0.986(17) . ?

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
C11 N10 H10A 115.1(10) . . ?
C11 N10 H10B 126.2(10) . . ?
H10A N10 H10B 118.6(15) . . ?
C14 N15 C16 118.20(11) . . ?
O10 C11 N10 123.03(11) . . ?
O10 C11 C12 118.58(11) . . ?
N10 C11 C12 118.37(11) . . ?
C17 C12 C13 118.49(11) . . ?
C17 C12 C11 118.37(11) . . ?
C13 C12 C11 123.11(11) . . ?
C14 C13 C12 118.47(12) . . ?
C14 C13 H13 118.1(10) . . ?
C12 C13 H13 123.4(10) . . ?
N15 C14 C13 123.14(12) . . ?
N15 C14 H14 115.6(9) . . ?
C13 C14 H14 121.2(9) . . ?
N15 C16 C17 122.61(12) . . ?
N15 C16 H16 116.9(10) . . ?
C17 C16 H16 120.4(10) . . ?
C12 C17 C16 119.08(12) . . ?
C12 C17 H17 122.7(9) . . ?
C16 C17 H17 118.2(9) . . ?
C1 O11 H11 110.0(10) . . ?
C2 O13 H13A 108.4(13) . . ?
O12 C1 O11 124.40(12) . . ?
O12 C1 C2 124.67(12) . . ?
O11 C1 C2 110.93(11) . . ?
O13 C2 C1 113.83(11) . . ?
O13 C2 H2A 109.2(10) . . ?
C1 C2 H2A 106.9(10) . . ?
O13 C2 H2B 114.2(10) . . ?
C1 C2 H2B 104.7(10) . . ?
H2A C2 H2B 107.7(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O10 C11 C12 C17 7.44(18) . . . . ?
N10 C11 C12 C17 -174.35(11) . . . . ?
O10 C11 C12 C13 -170.41(12) . . . . ?
N10 C11 C12 C13 7.80(19) . . . . ?
C17 C12 C13 C14 -0.83(19) . . . . ?
C11 C12 C13 C14 177.02(11) . . . . ?
C16 N15 C14 C13 -0.18(19) . . . . ?
C12 C13 C14 N15 1.0(2) . . . . ?
C14 N15 C16 C17 -0.73(19) . . . . ?
C13 C12 C17 C16 0.00(19) . . . . ?
C11 C12 C17 C16 -177.95(11) . . . . ?
N15 C16 C17 C12 0.8(2) . . . . ?
O12 C1 C2 O13 4.49(19) . . . . ?
O11 C1 C2 O13 -176.20(11) . . . . ?

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
N10 H10A O10 0.904(18) 2.023(19) 2.9261(15) 176.5(15) 2_666
N10 H10B O12 0.904(18) 2.073(18) 2.9761(15) 177.3(15) 1_655
O11 H11 N15 0.933(19) 1.684(19) 2.6116(14) 172.9(16) 2_765
O13 H13A O10 0.85(2) 1.97(2) 2.8047(15) 169.5(19) 2_666
C13 H13 O12 0.959(16) 2.363(16) 3.2537(16) 154.2(13) 1_655

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.057
