# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_20106z
_database_code_depnum_ccdc_archive 'CCDC 2166582'
loop_
_audit_author_name
_audit_author_address
'Victor G. Young'
;University of Minnesota
United States of America
;
_audit_update_record             
;
2022-04-14 deposited with the CCDC.	2022-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            2016z
_chemical_melting_point          128
_chemical_formula_moiety         ?
_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 0.0033 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           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                   20.8643(19)
_cell_length_b                   4.5307(4)
_cell_length_c                   8.7480(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.292(4)
_cell_angle_gamma                90
_cell_volume                     807.99(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    2182
_cell_measurement_theta_min      4.00
_cell_measurement_theta_max      30.44

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   0.6404
_exptl_transmission_factor_max   0.7461
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.025
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6404
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS-2016/2, Sheldrick'
_exptl_absorpt_special_details   ?
_exptl_special_details           'Yoon-Jung Jang / Prof. Mark Hillmyer'
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   micro-focus
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4006
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.998
_diffrn_reflns_theta_max         30.596
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1241
_reflns_number_gt                994
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0623P)²+0.2195P] 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         1241
_refine_ls_number_parameters     61
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1170
_refine_ls_wR_factor_gt          0.1093
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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 0.39045(4) 0.20928(18) 0.60488(9) 0.0189(2) Uani 1 1 d . . . . .
N1 N 0.41183(5) 0.4620(2) 0.39757(10) 0.0169(2) Uani 1 1 d D . . . .
H1A H 0.3975(6) 0.509(3) 0.2952(5) 0.020 Uiso 1 1 d D U . . .
C1 C 0.47082(5) 0.6052(2) 0.48462(13) 0.0176(2) Uani 1 1 d . . . . .
H1B H 0.462805 0.677769 0.585654 0.021 Uiso 1 1 calc R U . . .
H1C H 0.481187 0.777615 0.424690 0.021 Uiso 1 1 calc R U . . .
O2 O 0.31152(4) 0.20953(18) 0.19725(9) 0.0205(2) Uani 1 1 d D . . . .
H2A H 0.3357(6) 0.083(2) 0.1673(17) 0.025 Uiso 1 1 d D U . . .
C2 C 0.37607(5) 0.2785(2) 0.46375(12) 0.0149(2) Uani 1 1 d . . . . .
C3 C 0.31461(6) 0.1577(3) 0.35772(12) 0.0186(2) Uani 1 1 d . . . . .
H3A H 0.312423 -0.057688 0.375050 0.022 Uiso 1 1 calc R U . . .
H3B H 0.275810 0.248666 0.387141 0.022 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
O1 0.0232(5) 0.0209(4) 0.0125(4) -0.0001(3) 0.0036(3) -0.0006(3)
N1 0.0175(5) 0.0189(4) 0.0131(4) 0.0013(3) 0.0004(3) -0.0016(3)
C1 0.0187(5) 0.0157(5) 0.0175(5) -0.0009(4) 0.0017(4) -0.0017(4)
O2 0.0202(5) 0.0266(4) 0.0137(4) -0.0018(3) 0.0011(3) 0.0024(3)
C2 0.0164(5) 0.0152(5) 0.0136(5) -0.0022(3) 0.0041(4) 0.0022(4)
C3 0.0166(5) 0.0245(5) 0.0147(5) -0.0016(4) 0.0029(4) -0.0018(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
O1 C2 1.2468(12) . ?
N1 C2 1.3294(14) . ?
N1 C1 1.4550(14) . ?
N1 H1A 0.907(3) . ?
C1 C1 1.525(2) 5_666 ?
C1 H1B 0.9900 . ?
C1 H1C 0.9900 . ?
O2 C3 1.4112(13) . ?
O2 H2A 0.841(3) . ?
C2 C3 1.5159(15) . ?
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 N1 C1 122.79(9) . . ?
C2 N1 H1A 118.6(9) . . ?
C1 N1 H1A 118.5(9) . . ?
N1 C1 C1 111.62(11) . 5_666 ?
N1 C1 H1B 109.3 . . ?
C1 C1 H1B 109.3 5_666 . ?
N1 C1 H1C 109.3 . . ?
C1 C1 H1C 109.3 5_666 . ?
H1B C1 H1C 108.0 . . ?
C3 O2 H2A 107.1(10) . . ?
O1 C2 N1 123.33(10) . . ?
O1 C2 C3 120.60(10) . . ?
N1 C2 C3 116.06(9) . . ?
O2 C3 C2 113.71(9) . . ?
O2 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
O2 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?

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
C2 N1 C1 C1 77.71(15) . . . 5_666 ?
C1 N1 C2 O1 -1.26(17) . . . . ?
C1 N1 C2 C3 177.66(9) . . . . ?
O1 C2 C3 O2 -168.58(10) . . . . ?
N1 C2 C3 O2 12.47(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
_geom_hbond_publ_flag
N1 H1A O1 0.907(3) 2.079(7) 2.9132(12) 152.4(12) 6_565 yes
O2 H2A O1 0.841(3) 1.904(3) 2.7445(12) 178.2(15) 6 yes

_refine_diff_density_max         0.442
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.067

_shelx_res_file                  
;
TITL 20106z in C2/c
    20106z.res
    created by SHELXL-2018/3 at 13:59:19 on 10-Nov-2020
CELL  0.71073  20.8643   4.5307   8.7480   90.000  102.292   90.000
ZERR    4.000   0.0019   0.0004   0.0007    0.000    0.004    0.000
LATT  7
SYMM -X, Y, 1/2-Z
SFAC C  H  N O
UNIT 24 48 8 16
TEMP -148.150
SIZE 0.025 0.13 0.23

L.S. 10
ACTA
CONF
BOND $H
LIST 4
FMAP 2
PLAN 5
EQIV $2 x, -y+1, z-1/2
HTAB N1 O1_$2
EQIV $3 x, -y, z-1/2
HTAB O2 O1_$3
WGHT    0.062300    0.219500
FVAR       0.78362
O1    4    0.390446    0.209280    0.604877    11.00000    0.02320    0.02094 =
         0.01251   -0.00007    0.00362   -0.00063
N1    3    0.411826    0.462007    0.397567    11.00000    0.01753    0.01894 =
         0.01310    0.00134    0.00041   -0.00165
REM AFIX  43
DFIX 0.91 0.003 N1 H1A
H1A   2    0.397489    0.508539    0.295189    11.00000   -1.20000
REM AFIX   0
C1    1    0.470821    0.605210    0.484624    11.00000    0.01871    0.01572 =
         0.01753   -0.00093    0.00169   -0.00166
AFIX  23
H1B   2    0.462805    0.677769    0.585654    11.00000   -1.20000
H1C   2    0.481187    0.777615    0.424690    11.00000   -1.20000
AFIX   0
DFIX 0.84 0.003 O2 H2A
O2    4    0.311516    0.209530    0.197252    11.00000    0.02022    0.02659 =
         0.01373   -0.00184    0.00114    0.00244
H2A   2    0.335740    0.083473    0.167301    11.00000   -1.20000
C2    1    0.376070    0.278460    0.463755    11.00000    0.01642    0.01517 =
         0.01361   -0.00220    0.00406    0.00217
C3    1    0.314605    0.157678    0.357718    11.00000    0.01656    0.02452 =
         0.01467   -0.00159    0.00287   -0.00181
AFIX  23
H3A   2    0.312423   -0.057688    0.375050    11.00000   -1.20000
H3B   2    0.275810    0.248666    0.387141    11.00000   -1.20000
AFIX   0
HKLF 4




REM  20106z in C2/c
REM wR2 = 0.1170, GooF = S = 1.093, Restrained GooF = 1.093 for all data
REM R1 = 0.0392 for 994 Fo > 4sig(Fo) and 0.0496 for all 1241 data
REM 61 parameters refined using 2 restraints

END

WGHT      0.0622      0.2188

REM Highest difference peak  0.442,  deepest hole -0.247,  1-sigma level  0.067
Q1    1   0.5000  0.5000  0.5000  10.50000  0.05    0.44
Q2    1   0.3478  0.2021  0.4129  11.00000  0.05    0.36
Q3    1   0.4364  0.5383  0.4419  11.00000  0.05    0.30
Q4    1   0.3120  0.1754  0.2791  11.00000  0.05    0.23
Q5    1   0.2639  0.1552  0.1670  11.00000  0.05    0.21
;
_shelx_res_checksum              87324

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone and water'
####################################################################### 
# 
# 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_20090z
_database_code_depnum_ccdc_archive 'CCDC 2166583'
loop_
_audit_author_name
_audit_author_address
'Victor G. Young'
;University of Minnesota
United States of America
;
_audit_update_record             
;
2022-04-14 deposited with the CCDC.	2022-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            20090z
_chemical_melting_point          140
_chemical_formula_moiety         'C8 H16 N2 O4'
_chemical_formula_sum            'C8 H16 N2 O4'
_chemical_formula_weight         204.23

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

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

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

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

_cell_length_a                   8.1288(6)
_cell_length_b                   7.5360(6)
_cell_length_c                   8.5510(6)
_cell_angle_alpha                90
_cell_angle_beta                 113.285(2)
_cell_angle_gamma                90
_cell_volume                     481.16(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    2967
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      30.49

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             220
_exptl_transmission_factor_min   0.6915
_exptl_transmission_factor_max   0.7461
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6915
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS-2016/2, Sheldrick'
_exptl_absorpt_special_details   ?
_exptl_special_details           'Yoon-Jung Jang / Prof. M. Hillmyer'
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   micro-focus
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7826
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.728
_diffrn_reflns_theta_max         30.494
_diffrn_reflns_theta_full        25.242
_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             1473
_reflns_number_gt                1376
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0472P)²+0.1489P] 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         1473
_refine_ls_number_parameters     68
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0950
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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 0.57550(8) 0.26767(8) 0.57200(8) 0.01637(15) Uani 1 1 d . . . . .
H1A H 0.605141 0.165599 0.612941 0.020 Uiso 1 1 calc R U . . .
N1 N 0.22957(9) 0.27373(9) 0.53626(9) 0.01327(16) Uani 1 1 d . . . . .
H1B H 0.2709(17) 0.2195(17) 0.4739(17) 0.016 Uiso 1 1 d . U . . .
C1 C 0.53608(10) 0.37392(11) 0.68853(10) 0.01430(17) Uani 1 1 d . . . . .
H1C H 0.569714 0.498094 0.677368 0.017 Uiso 1 1 calc R U . . .
H1D H 0.610955 0.333907 0.805469 0.017 Uiso 1 1 calc R U . . .
O2 O 0.29350(8) 0.45419(8) 0.76562(8) 0.01619(15) Uani 1 1 d . . . . .
C2 C 0.34118(10) 0.36992(10) 0.66518(10) 0.01211(16) Uani 1 1 d . . . . .
C3 C 0.03915(10) 0.25614(10) 0.50308(11) 0.01499(17) Uani 1 1 d . . . . .
H3A H -0.032572 0.273692 0.379990 0.018 Uiso 1 1 calc R U . . .
H3B H 0.005500 0.350325 0.565615 0.018 Uiso 1 1 calc R U . . .
C4 C -0.00611(10) 0.07578(10) 0.55641(10) 0.01297(16) Uani 1 1 d . . . . .
H4A H -0.129131 0.079931 0.553211 0.016 Uiso 1 1 calc R U . . .
H4B H 0.076863 0.051639 0.675345 0.016 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
O1 0.0183(3) 0.0171(3) 0.0168(3) 0.0014(2) 0.0102(2) 0.0032(2)
N1 0.0125(3) 0.0123(3) 0.0166(3) -0.0018(2) 0.0075(2) -0.0018(2)
C1 0.0130(3) 0.0161(4) 0.0147(3) -0.0016(3) 0.0064(3) -0.0015(3)
O2 0.0186(3) 0.0155(3) 0.0174(3) -0.0022(2) 0.0102(2) 0.0002(2)
C2 0.0138(3) 0.0099(3) 0.0137(3) 0.0020(2) 0.0065(3) -0.0003(2)
C3 0.0110(3) 0.0124(3) 0.0211(4) 0.0009(3) 0.0059(3) -0.0003(2)
C4 0.0122(3) 0.0130(3) 0.0152(3) -0.0007(2) 0.0069(3) -0.0015(2)

_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 1.4103(10) . ?
O1 H1A 0.8400 . ?
N1 C2 1.3315(10) . ?
N1 C3 1.4652(10) . ?
N1 H1B 0.840(13) . ?
C1 C2 1.5169(11) . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
O2 C2 1.2467(9) . ?
C3 C4 1.5242(11) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C4 1.5234(15) 3_556 ?
C4 H4A 0.9900 . ?
C4 H4B 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
C1 O1 H1A 109.5 . . ?
C2 N1 C3 122.10(7) . . ?
C2 N1 H1B 118.6(9) . . ?
C3 N1 H1B 119.3(9) . . ?
O1 C1 C2 114.38(6) . . ?
O1 C1 H1C 108.7 . . ?
C2 C1 H1C 108.7 . . ?
O1 C1 H1D 108.7 . . ?
C2 C1 H1D 108.7 . . ?
H1C C1 H1D 107.6 . . ?
O2 C2 N1 123.51(7) . . ?
O2 C2 C1 119.48(7) . . ?
N1 C2 C1 117.02(7) . . ?
N1 C3 C4 112.59(6) . . ?
N1 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
N1 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C3 C4 C4 113.28(8) . 3_556 ?
C3 C4 H4A 108.9 . . ?
C4 C4 H4A 108.9 3_556 . ?
C3 C4 H4B 108.9 . . ?
C4 C4 H4B 108.9 3_556 . ?
H4A C4 H4B 107.7 . . ?

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 C2 O2 -1.12(12) . . . . ?
C3 N1 C2 C1 178.54(7) . . . . ?
O1 C1 C2 O2 177.39(7) . . . . ?
O1 C1 C2 N1 -2.29(10) . . . . ?
C2 N1 C3 C4 -104.79(8) . . . . ?
N1 C3 C4 C4 -70.02(10) . . . 3_556 ?

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
_geom_hbond_publ_flag
O1 H1A O2 0.84 1.90 2.7339(9) 170.2 2_646 yes
N1 H1B O2 0.840(13) 2.276(13) 3.0866(9) 162.4(12) 4_565 yes

_refine_diff_density_max         0.333
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.063

_shelx_res_file                  
;
TITL 20090Z in P2(1)/c
    20090z.res
    created by SHELXL-2018/3 at 15:28:41 on 28-Sep-2020
CELL 0.71073   8.12880   7.53600   8.55100  90.0000 113.2848  90.0000
ZERR    2.00   0.00060   0.00060   0.00060   0.0000   0.0023   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC C  H  N O
UNIT 16 32 4 8
SIZE  0.25 0.23 0.20
TEMP -148.150

L.S. 10
ACTA
CONF
BOND $H
LIST 4
FMAP 2
PLAN 5
EQIV $2 -x+1, y-1/2, -z+3/2
HTAB O1 O2_$2
EQIV $3 x, -y+1/2, z-1/2
HTAB N1 O2_$3
REM EQIV $4 -x+1, -y+1, -z+1
REM HTAB C1 O1_$4
REM EQIV $5 x, -y+1/2, z+1/2
REM HTAB C1 O1_$5
REM EQIV $6 -x, y-1/2, -z+3/2
REM HTAB C4 O2_$6

WGHT    0.047200    0.148900
FVAR       0.55202
O1    4    0.575501    0.267671    0.572004    11.00000    0.01834    0.01708 =
         0.01677    0.00144    0.01021    0.00319
AFIX 147
H1A   2    0.605141    0.165599    0.612941    11.00000   -1.20000
AFIX   0
N1    3    0.229569    0.273729    0.536264    11.00000    0.01250    0.01226 =
         0.01663   -0.00178    0.00746   -0.00182
H1B   2    0.270856    0.219492    0.473916    11.00000   -1.20000
C1    1    0.536083    0.373924    0.688530    11.00000    0.01299    0.01612 =
         0.01468   -0.00160    0.00644   -0.00147
AFIX  23
H1C   2    0.569714    0.498094    0.677368    11.00000   -1.20000
H1D   2    0.610955    0.333907    0.805469    11.00000   -1.20000
AFIX   0
O2    4    0.293504    0.454185    0.765617    11.00000    0.01858    0.01549 =
         0.01741   -0.00217    0.01023    0.00015
C2    1    0.341176    0.369915    0.665175    11.00000    0.01377    0.00991 =
         0.01367    0.00197    0.00650   -0.00026
C3    1    0.039147    0.256144    0.503082    11.00000    0.01100    0.01240 =
         0.02113    0.00086    0.00589   -0.00030
AFIX  23
H3A   2   -0.032572    0.273692    0.379990    11.00000   -1.20000
H3B   2    0.005500    0.350325    0.565615    11.00000   -1.20000
AFIX   0
C4    1   -0.006113    0.075784    0.556405    11.00000    0.01219    0.01297 =
         0.01518   -0.00075    0.00694   -0.00149
AFIX  23
H4A   2   -0.129131    0.079931    0.553211    11.00000   -1.20000
H4B   2    0.076863    0.051639    0.675345    11.00000   -1.20000
AFIX   0
HKLF 4




REM  20090Z in P2(1)/c
REM wR2 = 0.0950, GooF = S = 1.072, Restrained GooF = 1.072 for all data
REM R1 = 0.0347 for 1376 Fo > 4sig(Fo) and 0.0367 for all 1473 data
REM 68 parameters refined using 0 restraints

END

WGHT      0.0445      0.1543

REM Highest difference peak  0.333,  deepest hole -0.297,  1-sigma level  0.063
Q1    1   0.0000  0.0000  0.5000  10.50000  0.05    0.33
Q2    1   0.4428  0.3656  0.6722  11.00000  0.05    0.33
Q3    1   0.0266  0.1629  0.5321  11.00000  0.05    0.29
Q4    1   0.1396  0.1289  0.8347  11.00000  0.05    0.18
Q5    1   0.2825  0.3258  0.6015  11.00000  0.05    0.16
;
_shelx_res_checksum              52432

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone and water'
####################################################################### 
# 
# 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_20107z
_database_code_depnum_ccdc_archive 'CCDC 2166584'
loop_
_audit_author_name
_audit_author_address
'Victor G. Young'
;University of Minnesota
United States of America
;
_audit_update_record             
;
2022-04-14 deposited with the CCDC.	2022-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_melting_point          128
_chemical_formula_moiety         'C10 H20 N2 O4'
_chemical_formula_sum            'C10 H20 N2 O4'
_chemical_formula_weight         232.28

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           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                   25.3633(17)
_cell_length_b                   5.2161(3)
_cell_length_c                   8.9982(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.025(3)
_cell_angle_gamma                90
_cell_volume                     1159.81(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    2761
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      30.10

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6446
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS-2016/2, Sheldrick'
_exptl_absorpt_special_details   ?
_exptl_special_details           'Yoon-Jung Jang / Prof. Mark Hillmyer'
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   micro-focus
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5679
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.298
_diffrn_reflns_theta_max         30.757
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1794
_reflns_number_gt                1439
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0593P)²+0.3869P] 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         1794
_refine_ls_number_parameters     79
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1191
_refine_ls_wR_factor_gt          0.1093
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.65636(3) 0.23501(15) 0.39481(8) 0.0196(2) Uani 1 1 d . . . . .
N1 N 0.63618(4) 0.46119(17) 0.58897(9) 0.0162(2) Uani 1 1 d D . . . .
H1A H 0.6457(5) 0.497(3) 0.6903(4) 0.019 Uiso 1 1 d D U . . .
C1 C 0.51773(4) 0.9188(2) 0.46046(11) 0.0181(2) Uani 1 1 d . . . . .
H1B H 0.494542 0.796154 0.391017 0.022 Uiso 1 1 calc R U . . .
H1C H 0.535326 1.031915 0.397667 0.022 Uiso 1 1 calc R U . . .
O2 O 0.70471(4) 0.18438(16) 0.80085(9) 0.0196(2) Uani 1 1 d . . . . .
H2A H 0.6887(6) 0.056(3) 0.8320(15) 0.023 Uiso 1 1 d . U . . .
C2 C 0.56121(4) 0.7703(2) 0.57143(12) 0.0178(2) Uani 1 1 d . . . . .
H2B H 0.584565 0.891546 0.641491 0.021 Uiso 1 1 calc R U . . .
H2C H 0.543923 0.654090 0.633356 0.021 Uiso 1 1 calc R U . . .
C3 C 0.59554(4) 0.6147(2) 0.48642(11) 0.0180(2) Uani 1 1 d . . . . .
H3A H 0.571770 0.499950 0.412873 0.022 Uiso 1 1 calc R U . . .
H3B H 0.613841 0.732374 0.427843 0.022 Uiso 1 1 calc R U . . .
C4 C 0.66379(4) 0.28062(19) 0.53429(11) 0.0143(2) Uani 1 1 d . . . . .
C5 C 0.70538(5) 0.1301(2) 0.64777(11) 0.0169(2) Uani 1 1 d . . . . .
H5A H 0.698651 -0.055267 0.628886 0.020 Uiso 1 1 calc R U . . .
H5B H 0.741811 0.169007 0.631089 0.020 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
O1 0.0241(4) 0.0200(4) 0.0147(4) -0.0010(3) 0.0045(3) 0.0048(3)
N1 0.0173(5) 0.0168(4) 0.0141(4) -0.0008(3) 0.0027(3) 0.0039(3)
C1 0.0202(5) 0.0186(5) 0.0154(5) 0.0009(4) 0.0041(4) 0.0052(4)
O2 0.0246(4) 0.0189(4) 0.0150(4) 0.0018(3) 0.0040(3) -0.0026(3)
C2 0.0191(5) 0.0192(5) 0.0155(5) 0.0009(4) 0.0047(4) 0.0062(4)
C3 0.0193(5) 0.0199(5) 0.0145(4) 0.0009(4) 0.0032(4) 0.0070(4)
C4 0.0144(5) 0.0132(4) 0.0160(5) 0.0007(3) 0.0049(4) -0.0006(4)
C5 0.0171(5) 0.0170(5) 0.0169(5) 0.0019(4) 0.0047(4) 0.0031(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
O1 C4 1.2493(12) . ?
N1 C4 1.3322(13) . ?
N1 C3 1.4582(13) . ?
N1 H1A 0.909(2) . ?
C1 C2 1.5221(15) . ?
C1 C1 1.524(2) 5_676 ?
C1 H1B 0.9900 . ?
C1 H1C 0.9900 . ?
O2 C5 1.4100(12) . ?
O2 H2A 0.863(16) . ?
C2 C3 1.5173(14) . ?
C2 H2B 0.9900 . ?
C2 H2C 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5120(14) . ?
C5 H5A 0.9900 . ?
C5 H5B 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
C4 N1 C3 120.66(8) . . ?
C4 N1 H1A 118.4(9) . . ?
C3 N1 H1A 120.7(9) . . ?
C2 C1 C1 113.16(10) . 5_676 ?
C2 C1 H1B 108.9 . . ?
C1 C1 H1B 108.9 5_676 . ?
C2 C1 H1C 108.9 . . ?
C1 C1 H1C 108.9 5_676 . ?
H1B C1 H1C 107.8 . . ?
C5 O2 H2A 105.7(9) . . ?
C3 C2 C1 110.78(8) . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2B C2 H2C 108.1 . . ?
N1 C3 C2 112.26(8) . . ?
N1 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
N1 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
O1 C4 N1 122.20(9) . . ?
O1 C4 C5 120.26(9) . . ?
N1 C4 C5 117.54(9) . . ?
O2 C5 C4 113.29(9) . . ?
O2 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
O2 C5 H5B 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C1 C2 C3 -179.40(12) 5_676 . . . ?
C4 N1 C3 C2 168.56(10) . . . . ?
C1 C2 C3 N1 -177.53(9) . . . . ?
C3 N1 C4 O1 0.07(16) . . . . ?
C3 N1 C4 C5 179.79(9) . . . . ?
O1 C4 C5 O2 -173.38(9) . . . . ?
N1 C4 C5 O2 6.89(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
_geom_hbond_publ_flag
N1 H1A O1 0.909(2) 2.277(7) 3.1164(11) 153.4(12) 6_566 yes
O2 H2A O1 0.863(16) 1.871(16) 2.7334(11) 176.9(14) 6_556 yes

_refine_diff_density_max         0.319
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.109

_shelx_res_file                  
;
TITL 20107z in C2/c
    20107z.res
    created by SHELXL-2018/3 at 15:34:33 on 10-Nov-2020
CELL  0.71073  25.3633   5.2161   8.9982   90.000  103.025   90.000
ZERR    4.000   0.0017   0.0003   0.0004    0.000    0.003    0.000
LATT  7
SYMM -X, Y, 1/2-Z
SFAC C  H  N O
UNIT 40 80 8 16
TEMP -148.150
SIZE 0.21 0.06 0.04

L.S. 10
CONF
ACTA
BOND $H
LIST 4
FMAP 2
PLAN 5
EQIV $2 x, -y+1, z+1/2
HTAB N1 O1_$2
EQIV $3 x, -y, z+1/2
HTAB O2 O1_$3

WGHT    0.059300    0.386900
FVAR       0.73278
O1    4    0.656360    0.235014    0.394813    11.00000    0.02410    0.01996 =
         0.01474   -0.00101    0.00454    0.00484
DFIX  0.91 0.003 N1 H1A
N1    3    0.636180    0.461187    0.588967    11.00000    0.01730    0.01684 =
         0.01405   -0.00085    0.00273    0.00392
H1A   2    0.645667    0.497347    0.690305    11.00000   -1.20000
C1    1    0.517734    0.918806    0.460463    11.00000    0.02019    0.01865 =
         0.01545    0.00090    0.00406    0.00516
AFIX  23
H1B   2    0.494542    0.796154    0.391017    11.00000   -1.20000
H1C   2    0.535326    1.031915    0.397667    11.00000   -1.20000
AFIX   0
DFIX  0.91 0.003 N1 H1A
O2    4    0.704708    0.184381    0.800852    11.00000    0.02457    0.01892 =
         0.01500    0.00182    0.00404   -0.00262
H2A   2    0.688727    0.055708    0.831980    11.00000   -1.20000
C2    1    0.561208    0.770284    0.571433    11.00000    0.01914    0.01915 =
         0.01552    0.00088    0.00469    0.00623
AFIX  23
H2B   2    0.584565    0.891546    0.641491    11.00000   -1.20000
H2C   2    0.543923    0.654090    0.633356    11.00000   -1.20000
AFIX   0
C3    1    0.595544    0.614718    0.486424    11.00000    0.01926    0.01987 =
         0.01452    0.00086    0.00322    0.00697
AFIX  23
H3A   2    0.571770    0.499950    0.412873    11.00000   -1.20000
H3B   2    0.613841    0.732374    0.427843    11.00000   -1.20000
AFIX   0
C4    1    0.663788    0.280624    0.534290    11.00000    0.01439    0.01325 =
         0.01600    0.00074    0.00486   -0.00059
C5    1    0.705378    0.130129    0.647774    11.00000    0.01715    0.01703 =
         0.01686    0.00189    0.00468    0.00305
AFIX  23
H5A   2    0.698651   -0.055267    0.628886    11.00000   -1.20000
H5B   2    0.741811    0.169007    0.631089    11.00000   -1.20000
REM #####
AFIX   0
HKLF 4




REM  20107z in C2/c
REM wR2 = 0.1191, GooF = S = 1.088, Restrained GooF = 1.088 for all data
REM R1 = 0.0429 for 1439 Fo > 4sig(Fo) and 0.0551 for all 1794 data
REM 79 parameters refined using 2 restraints

END

WGHT      0.0574      0.4351

REM Highest difference peak  0.319,  deepest hole -0.363,  1-sigma level  0.109
Q1    1   0.6163  0.7252  0.3025  11.00000  0.05    0.32
Q2    1   0.6092  0.6586  0.4027  11.00000  0.05    0.31
Q3    1   0.7424  0.2458  0.5356  11.00000  0.05    0.30
Q4    1   0.6186  0.5316  0.5334  11.00000  0.05    0.29
Q5    1   0.5160  1.1784  0.2825  11.00000  0.05    0.29
;
_shelx_res_checksum              3462

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone and water'
