# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_19kaw15
_database_code_depnum_ccdc_archive 'CCDC 2017253'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2020-07-17 deposited with the CCDC.	2021-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H14 N O2, C6 H14 N O2, 2(C2 H O4)'
_chemical_formula_sum            'C16 H30 N2 O12'
_chemical_formula_weight         442.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.6883(2)
_cell_length_b                   9.7485(3)
_cell_length_c                   9.8768(4)
_cell_angle_alpha                81.291(2)
_cell_angle_beta                 74.807(2)
_cell_angle_gamma                81.290(2)
_cell_volume                     518.86(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7797
_cell_measurement_theta_min      4.62
_cell_measurement_theta_max      68.21
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.025
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_max          0.219


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             236
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    1.051
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_T_min  0.6825
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker AXS)
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microsource IuS Incoatec 3.0'
_diffrn_detector                 'Bruker Photon II CPAD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray

_diffrn_reflns_number            11263
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.620
_diffrn_reflns_theta_max         68.242
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             3656
_reflns_number_gt                3392
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.929
_reflns_Friedel_fraction_max     0.927
_reflns_Friedel_fraction_full    0.933

_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 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygenwere located in Fourier diff maps and assigned
 Uiso = 1.5xUeqiv.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0313P)²+0.1174P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1500 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(12)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3656
_refine_ls_number_parameters     305
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0761
_refine_ls_wR_factor_gt          0.0734
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0098(4) 0.4599(3) 0.2768(3) 0.0227(5) Uani 1 1 d . . . . .
O2 O 0.7618(4) 0.4759(2) 0.4938(2) 0.0182(5) Uani 1 1 d . . . . .
H1 H 1.056(7) 0.387(5) 0.307(5) 0.027 Uiso 1 1 d . U . . .
O3 O 0.0008(4) 0.5439(2) 0.7427(3) 0.0243(5) Uani 1 1 d . . . . .
H3 H -0.085(8) 0.628(5) 0.698(5) 0.036 Uiso 1 1 d . U . . .
O4 O 0.2380(4) 0.5202(2) 0.5250(3) 0.0198(5) Uani 1 1 d . . . . .
O5 O -0.1487(4) 1.1426(2) 0.3266(3) 0.0216(5) Uani 1 1 d . . . . .
H5 H -0.269(8) 1.110(5) 0.321(4) 0.032 Uiso 1 1 d . U . . .
O6 O 0.0308(4) 0.9220(2) 0.3489(2) 0.0200(5) Uani 1 1 d . . . . .
O7 O 0.4594(4) 1.0239(2) 0.3356(3) 0.0196(5) Uani 1 1 d . . . . .
O8 O 0.2513(4) 1.2339(2) 0.3638(2) 0.0178(5) Uani 1 1 d . . . . .
O9 O 1.1465(4) -0.1430(2) 0.6685(2) 0.0187(5) Uani 1 1 d . . . . .
H9 H 1.289(8) -0.092(4) 0.661(4) 0.028 Uiso 1 1 d . U . . .
O10 O 0.9535(4) 0.0756(2) 0.6570(3) 0.0210(5) Uani 1 1 d . . . . .
O11 O 0.5389(4) -0.0292(2) 0.6538(3) 0.0186(5) Uani 1 1 d . . . . .
O12 O 0.7477(4) -0.2415(2) 0.6440(2) 0.0174(5) Uani 1 1 d . . . . .
N1 N 0.5445(5) 0.7314(3) 0.4183(3) 0.0166(6) Uani 1 1 d . . . . .
H1B H 0.415(8) 0.687(4) 0.450(4) 0.025 Uiso 1 1 d . U . . .
H1C H 0.610(8) 0.732(4) 0.493(5) 0.025 Uiso 1 1 d . U . . .
H1A H 0.505(8) 0.815(5) 0.388(4) 0.025 Uiso 1 1 d . U . . .
N2 N 0.4357(6) 0.2637(3) 0.5965(3) 0.0186(6) Uani 1 1 d . . . . .
H2A H 0.498(8) 0.174(5) 0.627(4) 0.028 Uiso 1 1 d . U . . .
H2C H 0.391(8) 0.262(4) 0.514(5) 0.028 Uiso 1 1 d . U . . .
H2B H 0.559(8) 0.313(5) 0.577(4) 0.028 Uiso 1 1 d . U . . .
C1 C 0.8362(6) 0.5218(3) 0.3712(4) 0.0175(7) Uani 1 1 d . . . . .
C2 C 0.7318(6) 0.6621(3) 0.3055(3) 0.0167(7) Uani 1 1 d . . . . .
H2 H 0.867255 0.722213 0.265858 0.020 Uiso 1 1 calc R U . . .
C3 C 0.6206(6) 0.6402(3) 0.1861(3) 0.0190(6) Uani 1 1 d . . . . .
H3A H 0.481969 0.584204 0.227185 0.023 Uiso 1 1 calc R U . . .
H3B H 0.745830 0.584526 0.119598 0.023 Uiso 1 1 calc R U . . .
C4 C 0.5277(5) 0.7733(3) 0.1020(3) 0.0199(6) Uani 1 1 d . . . . .
H4 H 0.402264 0.830260 0.169088 0.024 Uiso 1 1 calc R U . . .
C5 C 0.7349(6) 0.8613(4) 0.0268(4) 0.0267(7) Uani 1 1 d . . . . .
H5A H 0.861574 0.806071 -0.037651 0.040 Uiso 1 1 calc R U . . .
H5B H 0.806327 0.889730 0.096880 0.040 Uiso 1 1 calc R U . . .
H5C H 0.669792 0.944580 -0.027028 0.040 Uiso 1 1 calc R U . . .
C6 C 0.4041(6) 0.7321(4) -0.0036(4) 0.0265(7) Uani 1 1 d . . . . .
H6A H 0.340416 0.816504 -0.056494 0.040 Uiso 1 1 calc R U . . .
H6B H 0.268663 0.678356 0.047354 0.040 Uiso 1 1 calc R U . . .
H6C H 0.524173 0.674889 -0.069352 0.040 Uiso 1 1 calc R U . . .
C7 C 0.1588(6) 0.4748(3) 0.6476(4) 0.0179(7) Uani 1 1 d . . . . .
C8 C 0.2229(6) 0.3238(3) 0.7055(4) 0.0203(7) Uani 1 1 d . . . . .
H8 H 0.080470 0.272988 0.709960 0.024 Uiso 1 1 calc R U . . .
C9 C 0.2670(6) 0.3017(3) 0.8534(3) 0.0223(7) Uani 1 1 d . . . . .
H9A H 0.138736 0.366045 0.910963 0.027 Uiso 1 1 calc R U . . .
C10 C 0.5164(6) 0.3427(4) 0.8549(4) 0.0270(7) Uani 1 1 d . . . . .
H10A H 0.648285 0.278711 0.801668 0.032 Uiso 1 1 calc R U . . .
H10B H 0.532208 0.438488 0.805888 0.032 Uiso 1 1 calc R U . . .
C11 C 0.5517(7) 0.3378(4) 1.0034(4) 0.0315(8) Uani 1 1 d . . . . .
H11A H 0.409646 0.390288 1.061002 0.047 Uiso 1 1 calc R U . . .
H11B H 0.700473 0.379536 0.998388 0.047 Uiso 1 1 calc R U . . .
H11C H 0.567690 0.240457 1.046211 0.047 Uiso 1 1 calc R U . . .
C12 C 0.2285(7) 0.1527(4) 0.9240(4) 0.0296(8) Uani 1 1 d . . . . .
H12A H 0.063916 0.133548 0.924790 0.044 Uiso 1 1 calc R U . . .
H12B H 0.245784 0.143538 1.021187 0.044 Uiso 1 1 calc R U . . .
H12C H 0.351359 0.085879 0.870973 0.044 Uiso 1 1 calc R U . . .
C13 C 0.0353(6) 1.0470(3) 0.3395(3) 0.0150(6) Uani 1 1 d . . . . .
C14 C 0.2679(6) 1.1085(3) 0.3458(3) 0.0142(6) Uani 1 1 d . . . . .
C15 C 0.9567(6) -0.0494(3) 0.6606(3) 0.0153(7) Uani 1 1 d . . . . .
C16 C 0.7291(6) -0.1140(3) 0.6533(3) 0.0152(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.310(4) . ?
O1 H1 0.76(4) . ?
O2 C1 1.212(4) . ?
O3 C7 1.308(4) . ?
O3 H3 1.00(4) . ?
O4 C7 1.215(4) . ?
O5 C13 1.310(4) . ?
O5 H5 0.82(5) . ?
O6 C13 1.212(4) . ?
O7 C14 1.255(4) . ?
O8 C14 1.247(4) . ?
O9 C15 1.315(4) . ?
O9 H9 0.99(4) . ?
O10 C15 1.211(4) . ?
O11 C16 1.257(4) . ?
O12 C16 1.247(4) . ?
N1 C2 1.490(4) . ?
N1 H1B 0.87(4) . ?
N1 H1C 0.91(5) . ?
N1 H1A 0.85(5) . ?
N2 C8 1.504(4) . ?
N2 H2A 0.93(5) . ?
N2 H2C 0.92(5) . ?
N2 H2B 0.88(5) . ?
C1 C2 1.527(4) . ?
C2 C3 1.531(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.533(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.527(5) . ?
C4 C6 1.530(5) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.523(5) . ?
C8 C9 1.525(5) . ?
C8 H8 1.0000 . ?
C9 C12 1.534(4) . ?
C9 C10 1.535(5) . ?
C9 H9A 1.0000 . ?
C10 C11 1.524(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.552(4) . ?
C15 C16 1.545(4) . ?

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 H1 111(3) . . ?
C7 O3 H3 111(3) . . ?
C13 O5 H5 113(3) . . ?
C15 O9 H9 108(2) . . ?
C2 N1 H1B 112(3) . . ?
C2 N1 H1C 109(3) . . ?
H1B N1 H1C 107(4) . . ?
C2 N1 H1A 110(3) . . ?
H1B N1 H1A 111(4) . . ?
H1C N1 H1A 108(4) . . ?
C8 N2 H2A 112(3) . . ?
C8 N2 H2C 111(3) . . ?
H2A N2 H2C 109(4) . . ?
C8 N2 H2B 112(3) . . ?
H2A N2 H2B 105(4) . . ?
H2C N2 H2B 108(4) . . ?
O2 C1 O1 126.1(3) . . ?
O2 C1 C2 123.3(3) . . ?
O1 C1 C2 110.6(3) . . ?
N1 C2 C1 108.5(3) . . ?
N1 C2 C3 111.2(3) . . ?
C1 C2 C3 110.2(3) . . ?
N1 C2 H2 108.9 . . ?
C1 C2 H2 108.9 . . ?
C3 C2 H2 108.9 . . ?
C2 C3 C4 116.0(2) . . ?
C2 C3 H3A 108.3 . . ?
C4 C3 H3A 108.3 . . ?
C2 C3 H3B 108.3 . . ?
C4 C3 H3B 108.3 . . ?
H3A C3 H3B 107.4 . . ?
C5 C4 C6 111.0(3) . . ?
C5 C4 C3 111.6(2) . . ?
C6 C4 C3 108.8(2) . . ?
C5 C4 H4 108.5 . . ?
C6 C4 H4 108.5 . . ?
C3 C4 H4 108.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O4 C7 O3 125.5(3) . . ?
O4 C7 C8 122.6(3) . . ?
O3 C7 C8 111.8(3) . . ?
N2 C8 C7 106.6(3) . . ?
N2 C8 C9 113.3(3) . . ?
C7 C8 C9 115.8(3) . . ?
N2 C8 H8 106.9 . . ?
C7 C8 H8 106.9 . . ?
C9 C8 H8 106.9 . . ?
C8 C9 C12 111.2(3) . . ?
C8 C9 C10 112.4(3) . . ?
C12 C9 C10 112.7(3) . . ?
C8 C9 H9A 106.7 . . ?
C12 C9 H9A 106.7 . . ?
C10 C9 H9A 106.7 . . ?
C11 C10 C9 113.3(3) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O6 C13 O5 125.4(3) . . ?
O6 C13 C14 121.3(3) . . ?
O5 C13 C14 113.3(3) . . ?
O8 C14 O7 125.3(3) . . ?
O8 C14 C13 119.2(3) . . ?
O7 C14 C13 115.6(3) . . ?
O10 C15 O9 125.5(3) . . ?
O10 C15 C16 121.4(3) . . ?
O9 C15 C16 113.1(2) . . ?
O12 C16 O11 125.6(3) . . ?
O12 C16 C15 119.1(3) . . ?
O11 C16 C15 115.3(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 N1 4.0(4) . . . . ?
O1 C1 C2 N1 -177.2(3) . . . . ?
O2 C1 C2 C3 -118.0(3) . . . . ?
O1 C1 C2 C3 60.8(3) . . . . ?
N1 C2 C3 C4 64.5(3) . . . . ?
C1 C2 C3 C4 -175.1(3) . . . . ?
C2 C3 C4 C5 61.9(3) . . . . ?
C2 C3 C4 C6 -175.3(3) . . . . ?
O4 C7 C8 N2 13.4(4) . . . . ?
O3 C7 C8 N2 -170.2(3) . . . . ?
O4 C7 C8 C9 140.5(3) . . . . ?
O3 C7 C8 C9 -43.2(4) . . . . ?
N2 C8 C9 C12 -79.0(4) . . . . ?
C7 C8 C9 C12 157.4(3) . . . . ?
N2 C8 C9 C10 48.5(4) . . . . ?
C7 C8 C9 C10 -75.2(4) . . . . ?
C8 C9 C10 C11 173.2(3) . . . . ?
C12 C9 C10 C11 -60.2(4) . . . . ?
O6 C13 C14 O8 -166.0(3) . . . . ?
O5 C13 C14 O8 12.6(4) . . . . ?
O6 C13 C14 O7 12.2(5) . . . . ?
O5 C13 C14 O7 -169.2(3) . . . . ?
O10 C15 C16 O12 173.3(3) . . . . ?
O9 C15 C16 O12 -5.6(4) . . . . ?
O10 C15 C16 O11 -4.9(4) . . . . ?
O9 C15 C16 O11 176.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O8 0.76(4) 1.83(4) 2.571(3) 164(4) 1_645 yes
O3 H3 O12 1.00(4) 1.58(5) 2.570(3) 172(4) 1_465 yes
O5 H5 O7 0.82(5) 1.83(5) 2.639(3) 171(4) 1_455 yes
O9 H9 O11 0.99(4) 1.61(4) 2.601(3) 172(4) 1_655 yes
N1 H1B O4 0.87(4) 1.99(4) 2.803(4) 155(4) . yes
N1 H1C O12 0.91(5) 1.92(5) 2.828(4) 173(4) 1_565 yes
N1 H1A O7 0.85(5) 2.02(5) 2.849(4) 168(4) . yes
N2 H2A O11 0.93(5) 1.94(5) 2.827(4) 158(4) . yes
N2 H2C O8 0.92(5) 1.93(5) 2.833(4) 169(4) 1_545 yes
N2 H2B O2 0.88(5) 2.04(5) 2.879(4) 159(4) . yes

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.039


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: H2O'
####################################################################### 
# 
# 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_twin4
_database_code_depnum_ccdc_archive 'CCDC 2017254'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2020-07-17 deposited with the CCDC.	2021-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H14 N O2, C5 H12 N O2, 2(C2 H O4)'
_chemical_formula_sum            'C15 H28 N2 O12'
_chemical_formula_weight         428.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.6561(5)
_cell_length_b                   9.5934(8)
_cell_length_c                   9.7572(9)
_cell_angle_alpha                85.735(3)
_cell_angle_beta                 75.315(3)
_cell_angle_gamma                82.514(3)
_cell_volume                     507.31(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9944
_cell_measurement_theta_min      4.65
_cell_measurement_theta_max      72.57
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.033
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_max          0.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             228
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?

_exptl_absorpt_coefficient_mu    1.057
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.467620
_exptl_absorpt_correction_T_max  0.753579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker AXS)
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microsource IuS Incoatec 3.0'
_diffrn_detector                 'Bruker Photon II CPAD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray

_diffrn_reflns_number            1772
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_av_R_equivalents  0.01643
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         4.653
_diffrn_reflns_theta_max         68.184
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.480
_diffrn_reflns_point_group_measured_fraction_full 0.481
_reflns_number_total             1772
_reflns_number_gt                1687
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen were located in Fourier diff maps and assigned
 Uiso = 1.2xUeqiv.

 Refined as a 2-component inversion twin.,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)+(0.1168P)²+0.2148P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.5(10)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         1772
_refine_ls_number_parameters     280
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.1741
_refine_ls_wR_factor_gt          0.1715
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0077(7) 0.4517(4) 0.2622(4) 0.0306(9) Uani 1 1 d D . . . .
H1 H 1.078(13) 0.371(6) 0.299(8) 0.046 Uiso 1 1 d D U . . .
O2 O 0.7566(6) 0.4803(4) 0.4788(4) 0.0278(9) Uani 1 1 d . . . . .
O3 O -0.0259(8) 0.5532(5) 0.7377(5) 0.0391(10) Uani 1 1 d D . . . .
H3 H -0.105(14) 0.625(8) 0.693(8) 0.059 Uiso 1 1 d D U . . .
O4 O 0.2257(6) 0.5214(4) 0.5213(4) 0.0288(9) Uani 1 1 d . . . . .
O5 O -0.1667(6) 1.1388(4) 0.3343(4) 0.0280(9) Uani 1 1 d D . . . .
H5 H -0.300(10) 1.093(8) 0.333(8) 0.042 Uiso 1 1 d D U . . .
O6 O 0.0132(7) 0.9153(4) 0.3479(4) 0.0272(8) Uani 1 1 d . . . . .
O7 O 0.4434(6) 1.0195(4) 0.3406(4) 0.0263(8) Uani 1 1 d . . . . .
O8 O 0.2481(6) 1.2351(4) 0.3559(4) 0.0283(9) Uani 1 1 d . . . . .
O9 O 1.1370(6) -0.1318(4) 0.6702(4) 0.0256(8) Uani 1 1 d D . . . .
H9 H 1.274(10) -0.086(7) 0.662(8) 0.038 Uiso 1 1 d D U . . .
O10 O 0.9549(7) 0.0886(4) 0.6569(4) 0.0293(9) Uani 1 1 d . . . . .
O11 O 0.5288(6) -0.0150(4) 0.6609(4) 0.0259(8) Uani 1 1 d . . . . .
O12 O 0.7317(6) -0.2317(4) 0.6416(4) 0.0247(8) Uani 1 1 d . . . . .
N1 N 0.5368(8) 0.7307(5) 0.4084(5) 0.0258(10) Uani 1 1 d . . . . .
H1A H 0.406743 0.679808 0.438511 0.039 Uiso 1 1 calc R U . . .
H1B H 0.484586 0.817288 0.375061 0.039 Uiso 1 1 calc R U . . .
H1C H 0.604248 0.740107 0.482029 0.039 Uiso 1 1 calc R U . . .
N2 N 0.4453(8) 0.2754(5) 0.5931(5) 0.0264(10) Uani 1 1 d . . . . .
H2A H 0.385541 0.270417 0.515529 0.040 Uiso 1 1 calc R U . . .
H2B H 0.491241 0.186905 0.624841 0.040 Uiso 1 1 calc R U . . .
H2C H 0.577834 0.324705 0.569378 0.040 Uiso 1 1 calc R U . . .
C1 C 0.8298(9) 0.5191(6) 0.3570(6) 0.0269(11) Uani 1 1 d . . . . .
C2 C 0.7256(9) 0.6563(6) 0.2924(6) 0.0256(11) Uani 1 1 d . . . . .
H2 H 0.861202 0.716472 0.253825 0.031 Uiso 1 1 calc R U . . .
C3 C 0.6126(10) 0.6252(6) 0.1714(6) 0.0268(11) Uani 1 1 d . . . . .
H3A H 0.739442 0.568908 0.101150 0.032 Uiso 1 1 calc R U . . .
H3B H 0.476711 0.566989 0.210843 0.032 Uiso 1 1 calc R U . . .
C4 C 0.5132(9) 0.7559(6) 0.0947(6) 0.0280(11) Uani 1 1 d . . . . .
H4 H 0.387352 0.813635 0.165878 0.034 Uiso 1 1 calc R U . . .
C5 C 0.3909(9) 0.7110(6) -0.0127(5) 0.0325(10) Uani 1 1 d . . . . .
H5A H 0.510684 0.650898 -0.080849 0.049 Uiso 1 1 calc R U . . .
H5B H 0.328833 0.794470 -0.063023 0.049 Uiso 1 1 calc R U . . .
H5C H 0.253651 0.658564 0.035867 0.049 Uiso 1 1 calc R U . . .
C6 C 0.7209(10) 0.8462(7) 0.0222(6) 0.0321(12) Uani 1 1 d . . . . .
H6A H 0.788872 0.880852 0.094443 0.048 Uiso 1 1 calc R U . . .
H6B H 0.654520 0.926252 -0.030620 0.048 Uiso 1 1 calc R U . . .
H6C H 0.851088 0.788880 -0.043174 0.048 Uiso 1 1 calc R U . . .
C7 C 0.1505(9) 0.4842(6) 0.6444(6) 0.0278(12) Uani 1 1 d . . . . .
C8 C 0.2505(10) 0.3476(6) 0.7070(7) 0.0310(12) Uani 1 1 d . . . . .
H8 H 0.114149 0.286849 0.739203 0.037 Uiso 1 1 calc R U . . .
C9 C 0.3496(12) 0.3706(7) 0.8340(7) 0.0376(14) Uani 1 1 d . . . . .
H9A H 0.225463 0.433277 0.899259 0.045 Uiso 1 1 calc R U . . .
H9B H 0.499451 0.418939 0.800497 0.045 Uiso 1 1 calc R U . . .
C10 C 0.4129(12) 0.2327(7) 0.9170(7) 0.0417(16) Uani 1 1 d . . . . .
H10A H 0.539827 0.171338 0.851878 0.050 Uiso 1 1 calc R U . . .
H10B H 0.485661 0.256057 0.993439 0.050 Uiso 1 1 calc R U . . .
C11 C 0.1995(15) 0.1512(9) 0.9820(9) 0.0551(19) Uani 1 1 d . . . . .
H11A H 0.063682 0.213916 1.037241 0.083 Uiso 1 1 calc R U . . .
H11B H 0.250224 0.074588 1.044482 0.083 Uiso 1 1 calc R U . . .
H11C H 0.145283 0.111817 0.906841 0.083 Uiso 1 1 calc R U . . .
C12 C 0.0208(9) 1.0411(6) 0.3414(6) 0.0240(11) Uani 1 1 d . . . . .
C13 C 0.2586(9) 1.1042(6) 0.3449(6) 0.0230(11) Uani 1 1 d . . . . .
C14 C 0.9548(9) -0.0379(6) 0.6612(5) 0.0241(11) Uani 1 1 d . . . . .
C15 C 0.7185(10) -0.1023(6) 0.6552(5) 0.0224(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.316(7) . ?
O1 H1 0.92(3) . ?
O2 C1 1.203(8) . ?
O3 C7 1.312(7) . ?
O3 H3 0.92(4) . ?
O4 C7 1.211(7) . ?
O5 C12 1.333(6) . ?
O5 H5 0.92(4) . ?
O6 C12 1.209(7) . ?
O7 C13 1.231(7) . ?
O8 C13 1.260(7) . ?
O9 C14 1.294(6) . ?
O9 H9 0.92(3) . ?
O10 C14 1.211(7) . ?
O11 C15 1.264(7) . ?
O12 C15 1.248(7) . ?
N1 C2 1.496(7) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N2 C8 1.491(7) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
C1 C2 1.529(7) . ?
C2 C3 1.542(7) . ?
C2 H2 1.0000 . ?
C3 C4 1.529(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.508(7) . ?
C4 C6 1.544(8) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.508(8) . ?
C8 C9 1.524(8) . ?
C8 H8 1.0000 . ?
C9 C10 1.549(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.501(12) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.554(7) . ?
C14 C15 1.559(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 113(5) . . ?
C7 O3 H3 110(5) . . ?
C12 O5 H5 108(5) . . ?
C14 O9 H9 108(5) . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C8 N2 H2A 109.5 . . ?
C8 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C8 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
O2 C1 O1 125.5(5) . . ?
O2 C1 C2 123.5(5) . . ?
O1 C1 C2 111.0(4) . . ?
N1 C2 C1 107.7(4) . . ?
N1 C2 C3 111.2(4) . . ?
C1 C2 C3 110.3(4) . . ?
N1 C2 H2 109.2 . . ?
C1 C2 H2 109.2 . . ?
C3 C2 H2 109.2 . . ?
C4 C3 C2 114.6(5) . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C5 C4 C3 109.2(5) . . ?
C5 C4 C6 110.7(4) . . ?
C3 C4 C6 111.1(4) . . ?
C5 C4 H4 108.6 . . ?
C3 C4 H4 108.6 . . ?
C6 C4 H4 108.6 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O4 C7 O3 125.5(5) . . ?
O4 C7 C8 122.5(5) . . ?
O3 C7 C8 112.0(5) . . ?
N2 C8 C7 108.1(4) . . ?
N2 C8 C9 111.3(5) . . ?
C7 C8 C9 112.0(5) . . ?
N2 C8 H8 108.4 . . ?
C7 C8 H8 108.4 . . ?
C9 C8 H8 108.4 . . ?
C8 C9 C10 113.6(5) . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 115.1(6) . . ?
C11 C10 H10A 108.5 . . ?
C9 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O6 C12 O5 125.4(5) . . ?
O6 C12 C13 121.4(4) . . ?
O5 C12 C13 113.2(5) . . ?
O7 C13 O8 125.0(5) . . ?
O7 C13 C12 116.2(5) . . ?
O8 C13 C12 118.8(4) . . ?
O10 C14 O9 126.5(5) . . ?
O10 C14 C15 120.2(4) . . ?
O9 C14 C15 113.3(4) . . ?
O12 C15 O11 125.7(5) . . ?
O12 C15 C14 118.9(4) . . ?
O11 C15 C14 115.4(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 N1 3.3(7) . . . . ?
O1 C1 C2 N1 -176.4(4) . . . . ?
O2 C1 C2 C3 -118.3(6) . . . . ?
O1 C1 C2 C3 62.0(5) . . . . ?
N1 C2 C3 C4 63.2(6) . . . . ?
C1 C2 C3 C4 -177.3(4) . . . . ?
C2 C3 C4 C5 -175.6(4) . . . . ?
C2 C3 C4 C6 62.1(6) . . . . ?
O4 C7 C8 N2 0.0(7) . . . . ?
O3 C7 C8 N2 178.8(5) . . . . ?
O4 C7 C8 C9 123.0(6) . . . . ?
O3 C7 C8 C9 -58.2(6) . . . . ?
N2 C8 C9 C10 -68.7(7) . . . . ?
C7 C8 C9 C10 170.2(5) . . . . ?
C8 C9 C10 C11 -61.9(8) . . . . ?
O6 C12 C13 O7 6.8(7) . . . . ?
O5 C12 C13 O7 -174.7(5) . . . . ?
O6 C12 C13 O8 -171.1(6) . . . . ?
O5 C12 C13 O8 7.4(6) . . . . ?
O10 C14 C15 O12 171.0(6) . . . . ?
O9 C14 C15 O12 -8.8(6) . . . . ?
O10 C14 C15 O11 -7.1(7) . . . . ?
O9 C14 C15 O11 173.1(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
_geom_hbond_publ_flag
O1 H1 O8 0.92(3) 1.66(4) 2.572(5) 171(7) 1_645 yes
O3 H3 O12 0.92(4) 1.67(4) 2.577(5) 170(9) 1_465 yes
O5 H5 O7 0.92(4) 1.68(4) 2.599(5) 175(7) 1_455 yes
O9 H9 O11 0.92(3) 1.67(4) 2.589(5) 174(7) 1_655 yes
N1 H1A O4 0.91 1.95 2.819(6) 158.5 . yes
N1 H1B O7 0.91 1.94 2.814(5) 161.0 . yes
N1 H1C O12 0.91 1.92 2.833(6) 176.7 1_565 yes
N2 H2A O8 0.91 1.98 2.882(6) 172.7 1_545 yes
N2 H2B O11 0.91 1.94 2.822(6) 163.8 . yes
N2 H2C O2 0.91 1.94 2.791(6) 154.3 . yes

_refine_diff_density_max         0.506
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.093


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: H2O'
####################################################################### 
# 
# 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_20kaw34
_database_code_depnum_ccdc_archive 'CCDC 2017249'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2020-07-17 deposited with the CCDC.	2021-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H12 N O2, C2 H O4'
_chemical_formula_sum            'C7 H13 N O6'
_chemical_formula_weight         207.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   5.7278(2)
_cell_length_b                   9.4026(3)
_cell_length_c                   9.8028(2)
_cell_angle_alpha                77.211(2)
_cell_angle_beta                 78.253(2)
_cell_angle_gamma                78.876(2)
_cell_volume                     497.98(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3353
_cell_measurement_theta_min      4.69
_cell_measurement_theta_max      68.08
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless

_exptl_crystal_size_min          0.052
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_max          0.197
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             220
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    1.058
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_T_min  0.6102
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker AXS)
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microsource IuS Incoatec 3.0'
_diffrn_detector                 'Bruker Photon II CPAD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray

_diffrn_reflns_number            5325
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.692
_diffrn_reflns_theta_max         68.282
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1802
_reflns_number_gt                1545
_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 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps and assigned
 Uiso = 1.5xUeqiv.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0390P)²+0.1855P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         1802
_refine_ls_number_parameters     143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0825
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.45416(19) 0.74703(12) 0.48135(11) 0.0230(3) Uani 1 1 d . . . . .
H1 H 0.523(4) 0.779(2) 0.394(2) 0.035 Uiso 1 1 d . U . . .
O2 O 0.26591(18) 0.98075(11) 0.47310(10) 0.0198(2) Uani 1 1 d . . . . .
O3 O 0.34271(18) 0.81479(12) 0.14975(10) 0.0203(3) Uani 1 1 d . . . . .
H3 H 0.220(4) 0.8205(19) 0.1051(19) 0.030 Uiso 1 1 d . U . . .
O4 O 0.55382(19) 0.83607(13) -0.07129(11) 0.0252(3) Uani 1 1 d . . . . .
O5 O 0.95845(18) 0.82994(12) 0.03513(10) 0.0206(3) Uani 1 1 d . . . . .
O6 O 0.73581(18) 0.83385(11) 0.24912(10) 0.0194(3) Uani 1 1 d . . . . .
N1 N 0.0311(2) 0.92783(15) 0.73967(13) 0.0185(3) Uani 1 1 d . . . . .
H1A H 0.098(4) 1.012(2) 0.7295(19) 0.028 Uiso 1 1 d . U . . .
H1B H -0.092(4) 0.9513(19) 0.686(2) 0.028 Uiso 1 1 d . U . . .
H1C H -0.035(3) 0.901(2) 0.833(2) 0.028 Uiso 1 1 d . U . . .
C1 C 0.3142(2) 0.85499(17) 0.53640(15) 0.0176(3) Uani 1 1 d . . . . .
C2 C 0.2197(3) 0.80720(17) 0.69322(15) 0.0194(3) Uani 1 1 d . . . . .
H2 H 0.356299 0.796943 0.745817 0.023 Uiso 1 1 calc R U . . .
C3 C 0.1255(3) 0.65984(17) 0.73095(15) 0.0214(3) Uani 1 1 d . . . . .
H3A H 0.067123 0.638153 0.834495 0.026 Uiso 1 1 calc R U . . .
H3B H 0.260979 0.581121 0.708388 0.026 Uiso 1 1 calc R U . . .
C4 C -0.0782(3) 0.65479(17) 0.65389(17) 0.0233(3) Uani 1 1 d . . . . .
H4A H -0.213718 0.734149 0.674626 0.028 Uiso 1 1 calc R U . . .
H4B H -0.019793 0.672866 0.550252 0.028 Uiso 1 1 calc R U . . .
C5 C -0.1676(3) 0.50664(19) 0.6990(2) 0.0324(4) Uani 1 1 d . . . . .
H5A H -0.032358 0.427546 0.682192 0.049 Uiso 1 1 calc R U . . .
H5B H -0.291255 0.504898 0.643649 0.049 Uiso 1 1 calc R U . . .
H5C H -0.236991 0.491923 0.800128 0.049 Uiso 1 1 calc R U . . .
C6 C 0.5399(3) 0.82586(15) 0.05506(15) 0.0169(3) Uani 1 1 d . . . . .
C7 C 0.7635(3) 0.82935(15) 0.12062(14) 0.0161(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3102(18) . ?
O1 H1 0.88(2) . ?
O2 C1 1.2161(18) . ?
O3 C6 1.3128(18) . ?
O3 H3 0.89(2) . ?
O4 C6 1.2082(17) . ?
O5 C7 1.2525(18) . ?
O6 C7 1.2464(17) . ?
N1 C2 1.4889(19) . ?
N1 H1A 0.92(2) . ?
N1 H1B 0.93(2) . ?
N1 H1C 0.92(2) . ?
C1 C2 1.519(2) . ?
C2 C3 1.526(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.526(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.520(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.5541(19) . ?

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 H1 111.4(13) . . ?
C6 O3 H3 108.6(12) . . ?
C2 N1 H1A 109.8(12) . . ?
C2 N1 H1B 111.7(11) . . ?
H1A N1 H1B 107.7(16) . . ?
C2 N1 H1C 110.3(11) . . ?
H1A N1 H1C 108.6(15) . . ?
H1B N1 H1C 108.7(17) . . ?
O2 C1 O1 125.40(13) . . ?
O2 C1 C2 122.37(13) . . ?
O1 C1 C2 112.21(13) . . ?
N1 C2 C1 108.10(12) . . ?
N1 C2 C3 111.35(12) . . ?
C1 C2 C3 114.38(12) . . ?
N1 C2 H2 107.6 . . ?
C1 C2 H2 107.6 . . ?
C3 C2 H2 107.6 . . ?
C2 C3 C4 114.24(12) . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C5 C4 C3 111.51(13) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O4 C6 O3 125.65(13) . . ?
O4 C6 C7 121.25(13) . . ?
O3 C6 C7 113.08(12) . . ?
O6 C7 O5 125.94(13) . . ?
O6 C7 C6 119.04(12) . . ?
O5 C7 C6 115.00(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 N1 11.12(18) . . . . ?
O1 C1 C2 N1 -170.26(11) . . . . ?
O2 C1 C2 C3 135.78(14) . . . . ?
O1 C1 C2 C3 -45.60(16) . . . . ?
N1 C2 C3 C4 64.84(16) . . . . ?
C1 C2 C3 C4 -58.08(17) . . . . ?
C2 C3 C4 C5 -178.58(13) . . . . ?
O4 C6 C7 O6 172.66(13) . . . . ?
O3 C6 C7 O6 -5.76(18) . . . . ?
O4 C6 C7 O5 -6.1(2) . . . . ?
O3 C6 C7 O5 175.46(12) . . . . ?

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 H1 O6 0.88(2) 1.73(2) 2.5771(14) 161.6(19) . yes
O3 H3 O5 0.89(2) 1.75(2) 2.6348(14) 173.8(18) 1_455 yes
N1 H1A O6 0.92(2) 1.95(2) 2.8529(17) 166.4(16) 2_676 yes
N1 H1B O2 0.93(2) 1.94(2) 2.8408(16) 161.9(17) 2_576 yes
N1 H1C O5 0.92(2) 1.94(2) 2.8082(16) 157.7(17) 1_456 yes

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.044


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: H2O'
####################################################################### 
# 
# 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_19kaw74_a
_database_code_depnum_ccdc_archive 'CCDC 2105696'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2021-08-26 deposited with the CCDC.	2021-11-11 downloaded from the CCDC.
;

_vrf_PLAT097_19kaw74_a           
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.76 eA-3  
RESPONSE: The large residual electron density (0.76 eA-3) peak at
 0.86 angstroms was assessed thoroughly.  While the distance suggests 
 a possible O-H hydrogen atom, the position of this peak does not create a viable
 hydrogen bond.  Additionally, adding a hydrogen atom to O2 does not make
 chemical sense.  
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H14 N O2, C2 H O4'
_chemical_formula_sum            'C8 H15 N O6'
_chemical_formula_weight         221.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           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                   5.6270(5)
_cell_length_b                   9.4327(9)
_cell_length_c                   10.4431(10)
_cell_angle_alpha                88.922(4)
_cell_angle_beta                 75.976(4)
_cell_angle_gamma                83.757(4)
_cell_volume                     534.57(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7746
_cell_measurement_theta_min      4.36
_cell_measurement_theta_max      68.36

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.028
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_max          0.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             236
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?

_exptl_absorpt_coefficient_mu    1.020
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.5918
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker AXS)
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microsource IuS Incoatec 3.0'
_diffrn_detector                 'Bruker Photon II CPAD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray

_diffrn_reflns_number            9427
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.364
_diffrn_reflns_theta_max         68.281
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1944
_reflns_number_gt                1788
_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 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps
 and assigned Uiso = 1.2xUeqiv.
The norleucinium fragment was modeled with two-part disorder with the
 occupancy factors of the two components refined to 91:9.  The adps of 
 several atom pairs (C2/C2A, C3/C3A, C4/C4A, C5/C5A, C1/C1A, C6/C6A,
 N1/N1A, and O1/O1A) for this disorder model were restrained using
 the SHELX EADP command.,whole molecule disorder of the leucinium fragment
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0713P)²+0.2219P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         1944
_refine_ls_number_parameters     188
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.1269
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.083
_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 0.8129(3) 0.44677(15) 0.22670(14) 0.0319(4) Uani 0.910(2) 1 d . . P A 1
O2 O 0.7466(3) 0.47814(14) 0.02505(14) 0.0350(4) Uani 0.910(2) 1 d . . P A 1
O3 O 1.13911(19) 0.23479(11) 0.14309(12) 0.0281(3) Uani 1 1 d . . . . .
O4 O 1.32147(19) 0.01426(11) 0.14732(12) 0.0272(3) Uani 1 1 d . . . . .
O5 O 0.8947(2) -0.08958(11) 0.13632(11) 0.0275(3) Uani 1 1 d . . . . .
O6 O 0.7059(2) 0.13363(12) 0.16212(12) 0.0284(3) Uani 1 1 d . . . . .
H6 H 0.586(4) 0.093(2) 0.155(2) 0.034 Uiso 1 1 d . U . . .
N1 N 0.4647(4) 0.7239(2) 0.08694(19) 0.0284(5) Uani 0.910(2) 1 d D . P A 1
H1A H 0.396(5) 0.815(3) 0.108(2) 0.034 Uiso 0.910(2) 1 d . U P A 1
H1B H 0.359(5) 0.682(3) 0.066(2) 0.034 Uiso 0.910(2) 1 d . U P A 1
H1C H 0.596(5) 0.732(2) 0.013(2) 0.034 Uiso 0.910(2) 1 d . U P A 1
C1 C 0.7140(4) 0.5138(2) 0.1391(2) 0.0276(5) Uani 0.910(2) 1 d D . P A 1
C2 C 0.5491(4) 0.64750(19) 0.1961(2) 0.0257(5) Uani 0.910(2) 1 d D . P A 1
H2 H 0.648808 0.710336 0.232983 0.031 Uiso 0.910(2) 1 calc R U P A 1
C3 C 0.3324(3) 0.61075(19) 0.30729(18) 0.0289(4) Uani 0.910(2) 1 d D . P A 1
H3A H 0.236104 0.546185 0.271766 0.035 Uiso 0.910(2) 1 calc R U P A 1
H3B H 0.397903 0.558582 0.376715 0.035 Uiso 0.910(2) 1 calc R U P A 1
C4 C 0.1613(4) 0.7402(3) 0.3695(2) 0.0320(6) Uani 0.910(2) 1 d D . P A 1
H4A H 0.099173 0.794274 0.299917 0.038 Uiso 0.910(2) 1 calc R U P A 1
H4B H 0.255418 0.803257 0.408207 0.038 Uiso 0.910(2) 1 calc R U P A 1
C5 C -0.0574(4) 0.6997(2) 0.4767(2) 0.0375(5) Uani 0.910(2) 1 d D . P A 1
H5A H -0.137698 0.626410 0.441031 0.045 Uiso 0.910(2) 1 calc R U P A 1
H5B H 0.003966 0.656966 0.551504 0.045 Uiso 0.910(2) 1 calc R U P A 1
C6 C -0.2464(5) 0.8247(3) 0.5271(3) 0.0482(7) Uani 0.910(2) 1 d D . P A 1
H6A H -0.172347 0.893799 0.569996 0.072 Uiso 0.910(2) 1 calc R U P A 1
H6B H -0.386915 0.791170 0.590900 0.072 Uiso 0.910(2) 1 calc R U P A 1
H6C H -0.302744 0.870260 0.452985 0.072 Uiso 0.910(2) 1 calc R U P A 1
C7 C 1.1387(3) 0.10265(16) 0.14739(15) 0.0229(4) Uani 1 1 d . . . . .
C8 C 0.8962(3) 0.03753(16) 0.14898(15) 0.0230(4) Uani 1 1 d . . . . .
H1 H 0.893(4) 0.372(2) 0.195(2) 0.028 Uiso 1 1 d . U . . .
O1A O 0.720(3) 0.4066(16) 0.2155(15) 0.0319(4) Uani 0.090(2) 1 d . . P A 2
O2A O 0.926(2) 0.5869(14) 0.1300(14) 0.033(3) Uani 0.090(2) 1 d . . P A 2
N1A N 0.497(5) 0.743(2) 0.118(2) 0.0284(5) Uani 0.090(2) 1 d D . P A 2
H1A1 H 0.372476 0.812685 0.150209 0.043 Uiso 0.090(2) 1 calc R U P A 2
H1A2 H 0.481885 0.711185 0.039154 0.043 Uiso 0.090(2) 1 calc R U P A 2
H1A3 H 0.644205 0.778502 0.107613 0.043 Uiso 0.090(2) 1 calc R U P A 2
C1A C 0.736(4) 0.539(2) 0.182(2) 0.0276(5) Uani 0.090(2) 1 d D . P A 2
C2A C 0.483(4) 0.623(2) 0.2129(19) 0.0257(5) Uani 0.090(2) 1 d D . P A 2
H2A H 0.362107 0.559842 0.195518 0.031 Uiso 0.090(2) 1 calc R U P A 2
C3A C 0.393(3) 0.679(2) 0.3518(16) 0.0289(4) Uani 0.090(2) 1 d D . P A 2
H3A1 H 0.474905 0.764403 0.361976 0.035 Uiso 0.090(2) 1 calc R U P A 2
H3A2 H 0.433788 0.605852 0.414295 0.035 Uiso 0.090(2) 1 calc R U P A 2
C4A C 0.113(4) 0.719(4) 0.383(3) 0.0320(6) Uani 0.090(2) 1 d D . P A 2
H4A1 H 0.074339 0.798047 0.325490 0.038 Uiso 0.090(2) 1 calc R U P A 2
H4A2 H 0.033202 0.635841 0.363563 0.038 Uiso 0.090(2) 1 calc R U P A 2
C5A C 0.011(4) 0.762(2) 0.5224(19) 0.0375(5) Uani 0.090(2) 1 d D . P A 2
H5A1 H -0.023878 0.674534 0.574784 0.045 Uiso 0.090(2) 1 calc R U P A 2
H5A2 H 0.139088 0.805055 0.553620 0.045 Uiso 0.090(2) 1 calc R U P A 2
C6A C -0.215(5) 0.863(4) 0.552(4) 0.0482(7) Uani 0.090(2) 1 d D . P A 2
H6A1 H -0.286314 0.869934 0.474473 0.072 Uiso 0.090(2) 1 calc R U P A 2
H6A2 H -0.175376 0.956508 0.572680 0.072 Uiso 0.090(2) 1 calc R U P A 2
H6A3 H -0.334925 0.828041 0.627134 0.072 Uiso 0.090(2) 1 calc R U P A 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 1.302(3) . ?
O1 H1 0.82(2) . ?
O2 C1 1.209(3) . ?
O3 C7 1.2466(19) . ?
O4 C7 1.2515(19) . ?
O5 C8 1.2098(19) . ?
O6 C8 1.3076(19) . ?
O6 H6 0.83(2) . ?
N1 C2 1.484(3) . ?
N1 H1A 0.91(3) . ?
N1 H1B 0.82(3) . ?
N1 H1C 0.94(3) . ?
C1 C2 1.520(3) . ?
C2 C3 1.532(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.520(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.527(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.509(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.553(2) . ?
O1A C1A 1.30(3) . ?
O1A H1 0.96(3) . ?
O2A C1A 1.21(3) . ?
N1A C2A 1.485(17) . ?
N1A H1A1 0.9100 . ?
N1A H1A2 0.9100 . ?
N1A H1A3 0.9100 . ?
C1A C2A 1.517(17) . ?
C2A C3A 1.503(17) . ?
C2A H2A 1.0000 . ?
C3A C4A 1.533(18) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C4A C5A 1.475(18) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C5A C6A 1.474(18) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6A H6A1 0.9800 . ?
C6A H6A2 0.9800 . ?
C6A H6A3 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 110.1(14) . . ?
C8 O6 H6 107.8(15) . . ?
C2 N1 H1A 114.0(15) . . ?
C2 N1 H1B 109.8(16) . . ?
H1A N1 H1B 106(2) . . ?
C2 N1 H1C 111.2(15) . . ?
H1A N1 H1C 105(2) . . ?
H1B N1 H1C 110(2) . . ?
O2 C1 O1 125.76(18) . . ?
O2 C1 C2 122.30(18) . . ?
O1 C1 C2 111.94(19) . . ?
N1 C2 C1 108.12(17) . . ?
N1 C2 C3 111.85(17) . . ?
C1 C2 C3 111.14(15) . . ?
N1 C2 H2 108.6 . . ?
C1 C2 H2 108.6 . . ?
C3 C2 H2 108.6 . . ?
C4 C3 C2 113.79(15) . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 C5 112.51(18) . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C6 C5 C4 113.2(2) . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 O4 125.59(13) . . ?
O3 C7 C8 119.03(13) . . ?
O4 C7 C8 115.36(13) . . ?
O5 C8 O6 125.95(14) . . ?
O5 C8 C7 121.05(13) . . ?
O6 C8 C7 112.99(13) . . ?
C1A O1A H1 100(2) . . ?
C2A N1A H1A1 109.5 . . ?
C2A N1A H1A2 109.5 . . ?
H1A1 N1A H1A2 109.5 . . ?
C2A N1A H1A3 109.5 . . ?
H1A1 N1A H1A3 109.5 . . ?
H1A2 N1A H1A3 109.5 . . ?
O2A C1A O1A 124.4(18) . . ?
O2A C1A C2A 125.2(19) . . ?
O1A C1A C2A 110.4(19) . . ?
N1A C2A C3A 109.8(16) . . ?
N1A C2A C1A 106.4(17) . . ?
C3A C2A C1A 115.2(17) . . ?
N1A C2A H2A 108.4 . . ?
C3A C2A H2A 108.4 . . ?
C1A C2A H2A 108.4 . . ?
C2A C3A C4A 109.8(15) . . ?
C2A C3A H3A1 109.7 . . ?
C4A C3A H3A1 109.7 . . ?
C2A C3A H3A2 109.7 . . ?
C4A C3A H3A2 109.7 . . ?
H3A1 C3A H3A2 108.2 . . ?
C5A C4A C3A 112.1(19) . . ?
C5A C4A H4A1 109.2 . . ?
C3A C4A H4A1 109.2 . . ?
C5A C4A H4A2 109.2 . . ?
C3A C4A H4A2 109.2 . . ?
H4A1 C4A H4A2 107.9 . . ?
C6A C5A C4A 117(2) . . ?
C6A C5A H5A1 108.1 . . ?
C4A C5A H5A1 108.1 . . ?
C6A C5A H5A2 108.1 . . ?
C4A C5A H5A2 108.1 . . ?
H5A1 C5A H5A2 107.3 . . ?
C5A C6A H6A1 109.5 . . ?
C5A C6A H6A2 109.5 . . ?
H6A1 C6A H6A2 109.5 . . ?
C5A C6A H6A3 109.5 . . ?
H6A1 C6A H6A3 109.5 . . ?
H6A2 C6A H6A3 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 N1 -4.8(3) . . . . ?
O1 C1 C2 N1 174.56(16) . . . . ?
O2 C1 C2 C3 118.3(2) . . . . ?
O1 C1 C2 C3 -62.3(2) . . . . ?
N1 C2 C3 C4 -59.5(2) . . . . ?
C1 C2 C3 C4 179.51(18) . . . . ?
C2 C3 C4 C5 178.08(18) . . . . ?
C3 C4 C5 C6 -172.5(2) . . . . ?
O3 C7 C8 O5 170.57(14) . . . . ?
O4 C7 C8 O5 -7.7(2) . . . . ?
O3 C7 C8 O6 -8.1(2) . . . . ?
O4 C7 C8 O6 173.66(13) . . . . ?
O2A C1A C2A N1A 25(3) . . . . ?
O1A C1A C2A N1A -153(2) . . . . ?
O2A C1A C2A C3A -97(3) . . . . ?
O1A C1A C2A C3A 85(2) . . . . ?
N1A C2A C3A C4A 78(3) . . . . ?
C1A C2A C3A C4A -162(2) . . . . ?
C2A C3A C4A C5A 175(2) . . . . ?
C3A C4A C5A C6A 152(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O6 H6 O4 0.83(2) 1.75(2) 2.5823(15) 176(2) 1_455 yes
N1^a H1A^a O4 0.91(3) 1.91(3) 2.809(2) 168(2) 1_465 yes
N1^a H1B^a O2^a 0.82(3) 2.01(3) 2.768(2) 152(2) 2_665 yes
N1^a H1C^a O3 0.94(3) 1.97(3) 2.907(2) 175(2) 2_765 yes
O1^a H1 O3 0.82(2) 1.78(2) 2.5732(17) 162(2) . yes
O1A^b H1 O3 0.96(3) 1.78(2) 2.667(15) 152(2) . yes
N1A^b H1A1^b O4 0.91 1.89 2.64(2) 137.5 1_465 yes
N1A^b H1A3^b O5 0.91 2.06 2.92(3) 158.4 1_565 yes

_refine_diff_density_max         0.763
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.067


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_19kaw63a
_database_code_depnum_ccdc_archive 'CCDC 2017256'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2020-07-17 deposited with the CCDC.	2021-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H14 N O2, C2 H O4'
_chemical_formula_sum            'C8 H15 N O6'
_chemical_formula_weight         221.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           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                   5.6792(4)
_cell_length_b                   9.5687(7)
_cell_length_c                   9.9416(8)
_cell_angle_alpha                84.722(3)
_cell_angle_beta                 74.876(3)
_cell_angle_gamma                82.793(3)
_cell_volume                     516.43(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9676
_cell_measurement_theta_min      4.62
_cell_measurement_theta_max      68.36
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.063
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_max          0.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_F_000             236
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?

_exptl_absorpt_coefficient_mu    1.056
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.6190
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker AXS)
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microsource IuS Incoatec 3.0'
_diffrn_detector                 'Bruker Photon II CPAD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray

_diffrn_reflns_number            10477
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.616
_diffrn_reflns_theta_max         68.359
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1874
_reflns_number_gt                1778
_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 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps and assigned
 Uiso = 1.5xUeqiv.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+0.2188P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         1874
_refine_ls_number_parameters     153
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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 0.51915(18) 0.45451(10) 0.76757(10) 0.0254(3) Uani 1 1 d . . . . .
H1 H 0.580(3) 0.371(2) 0.8082(19) 0.030 Uiso 1 1 d . U . . .
O2 O 0.26491(16) 0.48091(9) 0.98075(10) 0.0207(2) Uani 1 1 d . . . . .
O3 O 0.35010(16) 0.13854(10) 0.83306(10) 0.0219(2) Uani 1 1 d . . . . .
H3 H 0.218(3) 0.0932(18) 0.8321(17) 0.026 Uiso 1 1 d . U . . .
O4 O 0.52848(17) -0.08396(10) 0.84536(10) 0.0229(2) Uani 1 1 d . . . . .
O5 O 0.95623(16) 0.02046(9) 0.83965(10) 0.0208(2) Uani 1 1 d . . . . .
O6 O 0.75574(16) 0.23593(9) 0.86152(10) 0.0201(2) Uani 1 1 d . . . . .
N1 N 0.0477(2) 0.73014(12) 0.90876(12) 0.0195(3) Uani 1 1 d . . . . .
H1A H -0.082(3) 0.6776(18) 0.9387(17) 0.023 Uiso 1 1 d . U . . .
H1B H -0.001(3) 0.8225(19) 0.8786(17) 0.023 Uiso 1 1 d . U . . .
H1C H 0.105(3) 0.7399(17) 0.9845(19) 0.023 Uiso 1 1 d . U . . .
C1 C 0.3409(2) 0.52099(13) 0.85960(14) 0.0194(3) Uani 1 1 d . . . . .
C2 C 0.2382(2) 0.65785(13) 0.79567(14) 0.0204(3) Uani 1 1 d . . . . .
H2 H 0.373266 0.719522 0.758080 0.025 Uiso 1 1 calc R U . . .
C3 C 0.1289(2) 0.62910(14) 0.67661(14) 0.0219(3) Uani 1 1 d . . . . .
H3A H -0.012310 0.573852 0.716003 0.026 Uiso 1 1 calc R U . . .
H3B H 0.253612 0.569883 0.610465 0.026 Uiso 1 1 calc R U . . .
C4 C 0.0424(2) 0.76096(14) 0.59484(14) 0.0228(3) Uani 1 1 d . . . . .
H4 H -0.081162 0.821823 0.661818 0.027 Uiso 1 1 calc R U . . .
C5 C -0.0821(3) 0.71385(16) 0.49043(15) 0.0285(3) Uani 1 1 d . . . . .
H5A H -0.143633 0.796918 0.439363 0.043 Uiso 1 1 calc R U . . .
H5B H -0.219212 0.660954 0.540438 0.043 Uiso 1 1 calc R U . . .
H5C H 0.036661 0.653428 0.424454 0.043 Uiso 1 1 calc R U . . .
C6 C 0.2533(3) 0.84687(15) 0.52029(16) 0.0281(3) Uani 1 1 d . . . . .
H6A H 0.380291 0.786958 0.458041 0.042 Uiso 1 1 calc R U . . .
H6B H 0.323069 0.881881 0.589490 0.042 Uiso 1 1 calc R U . . .
H6C H 0.191919 0.926923 0.465490 0.042 Uiso 1 1 calc R U . . .
C7 C 0.5338(2) 0.04236(13) 0.84062(13) 0.0174(3) Uani 1 1 d . . . . .
C8 C 0.7686(2) 0.10679(13) 0.84693(13) 0.0167(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3148(16) . ?
O1 H1 0.93(2) . ?
O2 C1 1.2122(17) . ?
O3 C7 1.3149(16) . ?
O3 H3 0.917(19) . ?
O4 C7 1.2092(16) . ?
O5 C8 1.2541(16) . ?
O6 C8 1.2482(15) . ?
N1 C2 1.4944(16) . ?
N1 H1A 0.912(18) . ?
N1 H1B 0.938(18) . ?
N1 H1C 0.911(18) . ?
C1 C2 1.5192(18) . ?
C2 C3 1.5324(18) . ?
C2 H2 1.0000 . ?
C3 C4 1.5356(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.526(2) . ?
C4 C6 1.527(2) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.5553(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
C1 O1 H1 110.4(11) . . ?
C7 O3 H3 108.2(11) . . ?
C2 N1 H1A 109.4(10) . . ?
C2 N1 H1B 111.1(10) . . ?
H1A N1 H1B 111.9(15) . . ?
C2 N1 H1C 112.2(11) . . ?
H1A N1 H1C 107.0(14) . . ?
H1B N1 H1C 105.0(14) . . ?
O2 C1 O1 125.53(12) . . ?
O2 C1 C2 123.01(11) . . ?
O1 C1 C2 111.47(11) . . ?
N1 C2 C1 107.89(11) . . ?
N1 C2 C3 110.93(10) . . ?
C1 C2 C3 110.86(10) . . ?
N1 C2 H2 109.0 . . ?
C1 C2 H2 109.0 . . ?
C3 C2 H2 109.0 . . ?
C2 C3 C4 115.28(11) . . ?
C2 C3 H3A 108.5 . . ?
C4 C3 H3A 108.5 . . ?
C2 C3 H3B 108.5 . . ?
C4 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C5 C4 C6 110.71(12) . . ?
C5 C4 C3 108.26(11) . . ?
C6 C4 C3 112.15(11) . . ?
C5 C4 H4 108.5 . . ?
C6 C4 H4 108.5 . . ?
C3 C4 H4 108.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O4 C7 O3 125.77(12) . . ?
O4 C7 C8 121.26(11) . . ?
O3 C7 C8 112.95(11) . . ?
O6 C8 O5 125.72(11) . . ?
O6 C8 C7 118.93(11) . . ?
O5 C8 C7 115.33(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 N1 3.00(17) . . . . ?
O1 C1 C2 N1 -176.80(10) . . . . ?
O2 C1 C2 C3 -118.64(13) . . . . ?
O1 C1 C2 C3 61.55(14) . . . . ?
N1 C2 C3 C4 65.93(15) . . . . ?
C1 C2 C3 C4 -174.23(11) . . . . ?
C2 C3 C4 C5 -174.75(11) . . . . ?
C2 C3 C4 C6 62.82(15) . . . . ?
O4 C7 C8 O6 -170.01(11) . . . . ?
O3 C7 C8 O6 8.60(17) . . . . ?
O4 C7 C8 O5 8.46(18) . . . . ?
O3 C7 C8 O5 -172.93(10) . . . . ?

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 H1 O6 0.93(2) 1.66(2) 2.5773(13) 165.6(17) . yes
O3 H3 O5 0.917(19) 1.699(19) 2.6132(13) 174.8(16) 1_455 yes
N1 H1A O2 0.912(18) 1.940(18) 2.8127(15) 159.6(15) 2_567 yes
N1 H1B O5 0.938(18) 1.897(18) 2.8164(15) 166.1(15) 1_465 yes
N1 H1C O6 0.911(18) 1.940(19) 2.8504(15) 176.8(15) 2_667 yes

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: H2O'
####################################################################### 
# 
# 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_19kaw44
_database_code_depnum_ccdc_archive 'CCDC 2017255'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2020-07-17 deposited with the CCDC.	2021-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H14 N O2, C6H14 N O2, 2(C2 H O4)'
_chemical_formula_sum            'C16 H30 N2 O12'
_chemical_formula_weight         442.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.6629(5)
_cell_length_b                   9.5020(9)
_cell_length_c                   10.2123(10)
_cell_angle_alpha                95.275(6)
_cell_angle_beta                 101.163(5)
_cell_angle_gamma                97.232(5)
_cell_volume                     530.99(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5805
_cell_measurement_theta_min      4.44
_cell_measurement_theta_max      68.60
_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             236
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.326
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.068
_exptl_absorpt_coefficient_mu    1.027
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_T_min  0.5865
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker AXS)
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microsource IuS Incoatec 3.0'
_diffrn_detector                 'Bruker Photon II CPAD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray

_diffrn_reflns_number            7892
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.445
_diffrn_reflns_theta_max         68.591
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_point_group_measured_fraction_full 0.876
_reflns_number_total             3399
_reflns_number_gt                3072
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_max     0.757
_reflns_Friedel_fraction_full    0.766

_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 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen were located in Fourier diff maps and assigned
 Uiso = 1.2xUeqiv.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0893P)²+0.0094P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1189 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.23(19)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3399
_refine_ls_number_parameters     304
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1322
_refine_ls_wR_factor_gt          0.1265
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.060
_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 0.1563(5) 0.4722(3) 0.7407(3) 0.0302(7) Uani 1 1 d D . . . .
H1 H 0.068(10) 0.394(4) 0.702(6) 0.045 Uiso 1 1 d D U . . .
O2 O 0.2462(5) 0.4851(3) 0.5368(3) 0.0272(7) Uani 1 1 d . . . . .
O3 O 0.8344(6) 0.5320(3) 0.2933(3) 0.0316(7) Uani 1 1 d D . . . .
H3 H 0.939(9) 0.604(5) 0.332(6) 0.047 Uiso 1 1 d D U . . .
O4 O 0.7448(5) 0.5197(3) 0.4963(3) 0.0275(7) Uani 1 1 d . . . . .
O5 O 1.2751(5) 1.1506(3) 0.6731(3) 0.0276(7) Uani 1 1 d D . . . .
H5 H 1.409(7) 1.124(6) 0.665(6) 0.041 Uiso 1 1 d D U . . .
O6 O 1.0873(5) 0.9255(3) 0.6627(3) 0.0285(7) Uani 1 1 d . . . . .
O7 O 0.6636(5) 1.0315(3) 0.6689(3) 0.0260(7) Uani 1 1 d . . . . .
O8 O 0.8447(5) 1.2465(3) 0.6450(3) 0.0263(7) Uani 1 1 d . . . . .
O9 O -0.2749(5) -0.1490(3) 0.3501(3) 0.0286(7) Uani 1 1 d D . . . .
H9 H -0.390(9) -0.100(6) 0.349(6) 0.043 Uiso 1 1 d D U . . .
O10 O -0.0854(5) 0.0750(3) 0.3622(3) 0.0295(7) Uani 1 1 d . . . . .
O11 O 0.3370(5) -0.0301(3) 0.3576(3) 0.0274(7) Uani 1 1 d . . . . .
O12 O 0.1560(5) -0.2454(3) 0.3795(3) 0.0258(7) Uani 1 1 d . . . . .
N1 N 0.5274(7) 0.7370(4) 0.6083(4) 0.0273(8) Uani 1 1 d . . . . .
H1A H 0.615(11) 0.834(7) 0.633(6) 0.041 Uiso 1 1 d . U . . .
H1B H 0.407(13) 0.737(7) 0.539(6) 0.041 Uiso 1 1 d . U . . .
H1C H 0.634(12) 0.684(7) 0.582(6) 0.041 Uiso 1 1 d . U . . .
N2 N 0.4631(7) 0.2669(4) 0.4245(4) 0.0243(8) Uani 1 1 d . . . . .
H2B H 0.575(12) 0.275(6) 0.495(6) 0.036 Uiso 1 1 d . U . . .
H2A H 0.397(11) 0.180(7) 0.387(6) 0.036 Uiso 1 1 d . U . . .
H2C H 0.341(12) 0.311(7) 0.445(6) 0.036 Uiso 1 1 d . U . . .
C1 C 0.2656(8) 0.5319(4) 0.6534(5) 0.0245(9) Uani 1 1 d . . . . .
C2 C 0.4240(7) 0.6724(4) 0.7154(4) 0.0233(9) Uani 1 1 d . . . . .
H2 H 0.319539 0.738102 0.750258 0.028 Uiso 1 1 calc R U . . .
C3 C 0.6255(8) 0.6500(5) 0.8322(4) 0.0273(9) Uani 1 1 d . . . . .
H3A H 0.549871 0.595976 0.895673 0.033 Uiso 1 1 calc R U . . .
H3B H 0.734886 0.590205 0.796202 0.033 Uiso 1 1 calc R U . . .
C4 C 0.7796(8) 0.7868(5) 0.9105(5) 0.0308(10) Uani 1 1 d . . . . .
H4 H 0.855079 0.841973 0.846501 0.037 Uiso 1 1 calc R U . . .
C5 C 0.9833(9) 0.7452(6) 1.0156(5) 0.0408(10) Uani 1 1 d . . . . .
H5A H 1.089167 0.831683 1.063100 0.061 Uiso 1 1 calc R U . . .
H5B H 1.079037 0.684683 0.970711 0.061 Uiso 1 1 calc R U . . .
H5C H 0.911947 0.692544 1.080118 0.061 Uiso 1 1 calc R U . . .
C6 C 0.6279(8) 0.8809(5) 0.9780(4) 0.0387(9) Uani 1 1 d . . . . .
H6A H 0.506046 0.912118 0.909219 0.058 Uiso 1 1 calc R U . . .
H6B H 0.734271 0.964643 1.030681 0.058 Uiso 1 1 calc R U . . .
H6C H 0.545935 0.826421 1.037605 0.058 Uiso 1 1 calc R U . . .
C7 C 0.7259(8) 0.4721(5) 0.3799(4) 0.0264(9) Uani 1 1 d . . . . .
C8 C 0.5707(8) 0.3307(5) 0.3182(5) 0.0276(10) Uani 1 1 d . . . . .
H8 H 0.679534 0.265387 0.287381 0.033 Uiso 1 1 calc R U . . .
C9 C 0.3753(8) 0.3482(5) 0.1963(4) 0.0286(9) Uani 1 1 d . . . . .
H9A H 0.255417 0.403618 0.227244 0.034 Uiso 1 1 calc R U . . .
H9B H 0.452807 0.403638 0.134430 0.034 Uiso 1 1 calc R U . . .
C10 C 0.2418(9) 0.2057(5) 0.1197(5) 0.0300(10) Uani 1 1 d . . . . .
H10A H 0.363034 0.142820 0.104558 0.036 Uiso 1 1 calc R U . . .
H10B H 0.138207 0.158865 0.175638 0.036 Uiso 1 1 calc R U . . .
C11 C 0.0833(7) 0.2213(4) -0.0155(4) 0.0309(8) Uani 1 1 d . . . . .
H11A H 0.185237 0.274075 -0.068810 0.037 Uiso 1 1 calc R U . . .
H11B H 0.022507 0.124979 -0.064924 0.037 Uiso 1 1 calc R U . . .
C12 C -0.1330(8) 0.2985(5) -0.0051(4) 0.0406(10) Uani 1 1 d . . . . .
H12A H -0.230502 0.250354 0.051728 0.061 Uiso 1 1 calc R U . . .
H12B H -0.233310 0.297342 -0.095019 0.061 Uiso 1 1 calc R U . . .
H12C H -0.074665 0.397636 0.034671 0.061 Uiso 1 1 calc R U . . .
C13 C 1.0866(7) 1.0535(4) 0.6669(4) 0.0220(9) Uani 1 1 d . . . . .
C14 C 0.8445(7) 1.1182(5) 0.6604(4) 0.0236(9) Uani 1 1 d . . . . .
C15 C -0.0858(8) -0.0528(5) 0.3580(4) 0.0241(9) Uani 1 1 d . . . . .
C16 C 0.1559(7) -0.1156(4) 0.3646(4) 0.0221(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.311(6) . ?
O1 H1 0.86(3) . ?
O2 C1 1.212(6) . ?
O3 C7 1.304(6) . ?
O3 H3 0.85(3) . ?
O4 C7 1.211(5) . ?
O5 C13 1.307(5) . ?
O5 H5 0.85(3) . ?
O6 C13 1.214(5) . ?
O7 C14 1.254(5) . ?
O8 C14 1.243(6) . ?
O9 C15 1.302(5) . ?
O9 H9 0.85(3) . ?
O10 C15 1.211(6) . ?
O11 C16 1.244(5) . ?
O12 C16 1.257(5) . ?
N1 C2 1.482(6) . ?
N1 H1A 0.98(7) . ?
N1 H1B 0.88(7) . ?
N1 H1C 0.90(7) . ?
N2 C8 1.484(6) . ?
N2 H2B 0.85(6) . ?
N2 H2A 0.88(7) . ?
N2 H2C 0.90(6) . ?
C1 C2 1.520(6) . ?
C2 C3 1.534(6) . ?
C2 H2 1.0000 . ?
C3 C4 1.531(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C6 1.524(6) . ?
C4 C5 1.534(7) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.519(6) . ?
C8 C9 1.533(6) . ?
C8 H8 1.0000 . ?
C9 C10 1.528(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.525(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.520(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.564(5) . ?
C15 C16 1.553(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109(4) . . ?
C7 O3 H3 111(5) . . ?
C13 O5 H5 119(4) . . ?
C15 O9 H9 103(4) . . ?
C2 N1 H1A 116(3) . . ?
C2 N1 H1B 108(4) . . ?
H1A N1 H1B 109(6) . . ?
C2 N1 H1C 109(4) . . ?
H1A N1 H1C 106(5) . . ?
H1B N1 H1C 109(6) . . ?
C8 N2 H2B 108(4) . . ?
C8 N2 H2A 104(4) . . ?
H2B N2 H2A 117(6) . . ?
C8 N2 H2C 113(4) . . ?
H2B N2 H2C 108(5) . . ?
H2A N2 H2C 106(6) . . ?
O2 C1 O1 126.0(4) . . ?
O2 C1 C2 122.3(4) . . ?
O1 C1 C2 111.7(4) . . ?
N1 C2 C1 108.1(3) . . ?
N1 C2 C3 111.2(3) . . ?
C1 C2 C3 111.3(4) . . ?
N1 C2 H2 108.7 . . ?
C1 C2 H2 108.7 . . ?
C3 C2 H2 108.7 . . ?
C4 C3 C2 115.3(4) . . ?
C4 C3 H3A 108.4 . . ?
C2 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
C2 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
C6 C4 C3 112.0(4) . . ?
C6 C4 C5 110.4(4) . . ?
C3 C4 C5 108.5(4) . . ?
C6 C4 H4 108.6 . . ?
C3 C4 H4 108.6 . . ?
C5 C4 H4 108.6 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O4 C7 O3 125.6(4) . . ?
O4 C7 C8 122.7(4) . . ?
O3 C7 C8 111.7(4) . . ?
N2 C8 C7 108.2(4) . . ?
N2 C8 C9 111.9(4) . . ?
C7 C8 C9 112.0(4) . . ?
N2 C8 H8 108.2 . . ?
C7 C8 H8 108.2 . . ?
C9 C8 H8 108.2 . . ?
C10 C9 C8 113.1(4) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 113.3(4) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C10 114.2(4) . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O6 C13 O5 126.2(3) . . ?
O6 C13 C14 121.0(4) . . ?
O5 C13 C14 112.8(3) . . ?
O8 C14 O7 125.9(4) . . ?
O8 C14 C13 119.0(4) . . ?
O7 C14 C13 115.0(4) . . ?
O10 C15 O9 126.2(4) . . ?
O10 C15 C16 120.1(4) . . ?
O9 C15 C16 113.7(3) . . ?
O11 C16 O12 125.3(4) . . ?
O11 C16 C15 116.0(4) . . ?
O12 C16 C15 118.7(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 N1 3.1(5) . . . . ?
O1 C1 C2 N1 -176.4(3) . . . . ?
O2 C1 C2 C3 -119.3(4) . . . . ?
O1 C1 C2 C3 61.2(4) . . . . ?
N1 C2 C3 C4 65.2(4) . . . . ?
C1 C2 C3 C4 -174.2(4) . . . . ?
C2 C3 C4 C6 62.2(5) . . . . ?
C2 C3 C4 C5 -175.6(4) . . . . ?
O4 C7 C8 N2 -1.7(5) . . . . ?
O3 C7 C8 N2 177.5(3) . . . . ?
O4 C7 C8 C9 122.1(4) . . . . ?
O3 C7 C8 C9 -58.6(4) . . . . ?
N2 C8 C9 C10 -66.8(4) . . . . ?
C7 C8 C9 C10 171.4(4) . . . . ?
C8 C9 C10 C11 -168.9(4) . . . . ?
C9 C10 C11 C12 -66.7(5) . . . . ?
O6 C13 C14 O8 -169.5(4) . . . . ?
O5 C13 C14 O8 8.7(5) . . . . ?
O6 C13 C14 O7 9.1(6) . . . . ?
O5 C13 C14 O7 -172.6(3) . . . . ?
O10 C15 C16 O11 -8.5(6) . . . . ?
O9 C15 C16 O11 172.5(4) . . . . ?
O10 C15 C16 O12 169.9(4) . . . . ?
O9 C15 C16 O12 -9.1(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O8 0.86(3) 1.74(3) 2.581(4) 167(6) 1_445 yes
O3 H3 O12 0.85(3) 1.73(3) 2.575(4) 169(7) 1_665 yes
O5 H5 O7 0.85(3) 1.78(3) 2.603(4) 165(6) 1_655 yes
O9 H9 O11 0.85(3) 1.77(3) 2.605(4) 167(6) 1_455 yes
N1 H1A O7 0.98(7) 1.85(6) 2.786(5) 159(5) . yes
N1 H1B O12 0.88(7) 1.98(7) 2.858(5) 174(6) 1_565 yes
N1 H1C O4 0.90(7) 1.95(7) 2.800(4) 158(6) . yes
N2 H2B O8 0.85(6) 2.00(7) 2.842(5) 166(5) 1_545 yes
N2 H2A O11 0.88(7) 1.97(7) 2.808(5) 160(6) . yes
N2 H2C O2 0.90(6) 2.01(6) 2.806(4) 147(6) . yes

_refine_diff_density_max         0.392
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.074


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: H2O'
####################################################################### 
# 
# 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_20kaw07
_database_code_depnum_ccdc_archive 'CCDC 2017245'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2020-07-17 deposited with the CCDC.	2021-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H14 N O2, C2 H O4'
_chemical_formula_sum            'C8 H15 N O6'
_chemical_formula_weight         221.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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/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                   9.7133(5)
_cell_length_b                   5.7496(3)
_cell_length_c                   19.3839(12)
_cell_angle_alpha                90
_cell_angle_beta                 104.238(2)
_cell_angle_gamma                90
_cell_volume                     1049.29(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9949
_cell_measurement_theta_min      4.71
_cell_measurement_theta_max      72.29
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless

_exptl_crystal_size_min          0.095
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_max          0.219
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    1.039
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.6928
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker AXS)
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microsource IuS Incoatec 3.0'
_diffrn_detector                 'Bruker Photon II CPAD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray

_diffrn_reflns_number            15413
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.707
_diffrn_reflns_theta_max         72.284
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2043
_reflns_number_gt                2008
_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 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen were located in Fourier diff maps and assigned
 Uiso = 1.5xUeqiv.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0358P)²+0.4519P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         2043
_refine_ls_number_parameters     153
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0768
_refine_ls_wR_factor_gt          0.0765
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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 0.26008(8) 0.38580(14) 0.48304(4) 0.01785(19) Uani 1 1 d . . . . .
H1 H 0.2621(15) 0.437(3) 0.4414(8) 0.027 Uiso 1 1 d . U . . .
O2 O 0.47828(7) 0.24829(13) 0.48706(4) 0.01469(18) Uani 1 1 d . . . . .
O3 O 0.66745(8) -0.51524(13) 0.81867(4) 0.01649(18) Uani 1 1 d . . . . .
H3 H 0.6392(15) -0.657(3) 0.8005(8) 0.025 Uiso 1 1 d . U . . .
O4 O 0.53211(8) -0.36709(13) 0.71672(4) 0.01813(18) Uani 1 1 d . . . . .
O5 O 0.59861(8) 0.06762(13) 0.77206(4) 0.01569(18) Uani 1 1 d . . . . .
O6 O 0.75116(8) -0.09774(13) 0.86508(4) 0.01632(18) Uani 1 1 d . . . . .
N1 N 0.51885(9) 0.08943(16) 0.62049(5) 0.01298(19) Uani 1 1 d . . . . .
H1A H 0.6002(15) 0.171(3) 0.6215(7) 0.019 Uiso 1 1 d . U . . .
H1C H 0.5267(14) 0.045(2) 0.6666(8) 0.019 Uiso 1 1 d . U . . .
H1B H 0.5156(14) -0.038(3) 0.5934(7) 0.019 Uiso 1 1 d . U . . .
C1 C 0.38113(10) 0.28771(17) 0.51462(5) 0.0126(2) Uani 1 1 d . . . . .
C2 C 0.38947(10) 0.23441(18) 0.59240(5) 0.0128(2) Uani 1 1 d . . . . .
H2 H 0.403967 0.385466 0.618771 0.015 Uiso 1 1 calc R U . . .
C3 C 0.25393(11) 0.12288(18) 0.60521(5) 0.0142(2) Uani 1 1 d . . . . .
H3A H 0.172442 0.223792 0.581061 0.017 Uiso 1 1 calc R U . . .
C4 C 0.22630(11) -0.11919(19) 0.57170(6) 0.0192(2) Uani 1 1 d . . . . .
H4A H 0.226435 -0.108661 0.520741 0.023 Uiso 1 1 calc R U . . .
H4B H 0.304734 -0.224100 0.595112 0.023 Uiso 1 1 calc R U . . .
C5 C 0.08566(12) -0.2246(2) 0.57797(7) 0.0275(3) Uani 1 1 d . . . . .
H5A H 0.091139 -0.261879 0.627907 0.041 Uiso 1 1 calc R U . . .
H5B H 0.066723 -0.366823 0.549356 0.041 Uiso 1 1 calc R U . . .
H5C H 0.008829 -0.112636 0.560682 0.041 Uiso 1 1 calc R U . . .
C6 C 0.25835(13) 0.1235(2) 0.68452(6) 0.0252(3) Uani 1 1 d . . . . .
H6A H 0.330006 0.012265 0.709342 0.038 Uiso 1 1 calc R U . . .
H6B H 0.165051 0.079039 0.691148 0.038 Uiso 1 1 calc R U . . .
H6C H 0.282821 0.279660 0.703960 0.038 Uiso 1 1 calc R U . . .
C7 C 0.61185(10) -0.34583(18) 0.77501(5) 0.0119(2) Uani 1 1 d . . . . .
C8 C 0.65876(10) -0.10241(18) 0.80737(5) 0.0118(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3120(13) . ?
O1 H1 0.865(16) . ?
O2 C1 1.2145(13) . ?
O3 C7 1.3160(13) . ?
O3 H3 0.906(16) . ?
O4 C7 1.2087(12) . ?
O5 C8 1.2525(13) . ?
O6 C8 1.2505(12) . ?
N1 C2 1.4946(13) . ?
N1 H1A 0.916(15) . ?
N1 H1C 0.914(15) . ?
N1 H1B 0.899(15) . ?
C1 C2 1.5210(13) . ?
C2 C3 1.5385(14) . ?
C2 H2 1.0000 . ?
C3 C6 1.5274(14) . ?
C3 C4 1.5314(15) . ?
C3 H3A 1.0000 . ?
C4 C5 1.5263(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.5554(14) . ?

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 H1 111.1(10) . . ?
C7 O3 H3 112.4(9) . . ?
C2 N1 H1A 111.4(9) . . ?
C2 N1 H1C 111.9(9) . . ?
H1A N1 H1C 105.1(12) . . ?
C2 N1 H1B 109.7(9) . . ?
H1A N1 H1B 109.8(12) . . ?
H1C N1 H1B 108.9(13) . . ?
O2 C1 O1 125.38(9) . . ?
O2 C1 C2 122.73(9) . . ?
O1 C1 C2 111.85(9) . . ?
N1 C2 C1 107.97(8) . . ?
N1 C2 C3 112.64(8) . . ?
C1 C2 C3 113.89(8) . . ?
N1 C2 H2 107.3 . . ?
C1 C2 H2 107.3 . . ?
C3 C2 H2 107.3 . . ?
C6 C3 C4 112.81(9) . . ?
C6 C3 C2 110.37(9) . . ?
C4 C3 C2 112.21(8) . . ?
C6 C3 H3A 107.0 . . ?
C4 C3 H3A 107.0 . . ?
C2 C3 H3A 107.0 . . ?
C5 C4 C3 113.20(9) . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.8 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O4 C7 O3 126.41(10) . . ?
O4 C7 C8 121.65(9) . . ?
O3 C7 C8 111.93(8) . . ?
O6 C8 O5 127.43(9) . . ?
O6 C8 C7 117.04(9) . . ?
O5 C8 C7 115.53(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 N1 -11.11(13) . . . . ?
O1 C1 C2 N1 170.84(8) . . . . ?
O2 C1 C2 C3 -137.00(10) . . . . ?
O1 C1 C2 C3 44.96(12) . . . . ?
N1 C2 C3 C6 68.84(11) . . . . ?
C1 C2 C3 C6 -167.77(9) . . . . ?
N1 C2 C3 C4 -57.91(11) . . . . ?
C1 C2 C3 C4 65.47(11) . . . . ?
C6 C3 C4 C5 59.68(13) . . . . ?
C2 C3 C4 C5 -174.90(9) . . . . ?
O4 C7 C8 O6 -173.78(9) . . . . ?
O3 C7 C8 O6 7.06(12) . . . . ?
O4 C7 C8 O5 6.26(14) . . . . ?
O3 C7 C8 O5 -172.90(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
_geom_hbond_publ_flag
O3 H3 O5 0.906(16) 1.689(16) 2.5920(10) 174.9(14) 1_545 yes
N1 H1A O3 0.916(15) 2.511(14) 3.0447(11) 117.5(11) 2_656 yes
N1 H1A O6 0.916(15) 1.931(15) 2.8278(12) 165.6(13) 2_656 yes
N1 H1C O4 0.914(15) 2.555(15) 3.2043(12) 128.4(11) . yes
N1 H1C O5 0.914(15) 1.996(15) 2.8509(11) 155.0(13) . yes
N1 H1B O2 0.899(15) 1.985(15) 2.8542(12) 162.3(13) 3_656 yes
O1 H1 O6 0.865(16) 1.724(17) 2.5736(10) 166.7(15) 4_565 yes

_refine_diff_density_max         0.310
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.043


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: H2O'
####################################################################### 
# 
# 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_20kaw21_a
_database_code_depnum_ccdc_archive 'CCDC 2017247'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2020-07-17 deposited with the CCDC.	2021-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H14 N O2, C5 H12 N O2, 2(C2 H O4)'
_chemical_formula_sum            'C15 H28 N2 O12'
_chemical_formula_weight         428.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.7100(4)
_cell_length_b                   9.5809(7)
_cell_length_c                   9.8621(7)
_cell_angle_alpha                74.666(3)
_cell_angle_beta                 79.160(3)
_cell_angle_gamma                79.281(3)
_cell_volume                     505.72(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    173.15(2)
_cell_measurement_reflns_used    7812
_cell_measurement_theta_min      4.70
_cell_measurement_theta_max      72.15


_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             228
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.356
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.043
_exptl_absorpt_coefficient_mu    1.060
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_T_min  0.6201
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker AXS)
;

_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      173.15(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microsource IuS Incoatec 3.0'
_diffrn_detector                 'Bruker Photon II CPAD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray

_diffrn_reflns_number            12329
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.700
_diffrn_reflns_theta_max         72.193
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             3780
_reflns_number_gt                3501
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_max     0.914
_reflns_Friedel_fraction_full    0.933

_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 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (1.5xUeqiv for methyl groups). Those H atoms
 attached to nitrogen and oxygen were located in Fourier diff maps and assigned
 Uiso = 1.5xUeqiv with N-H and O-H restrained to 0.85(2).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0330P)²+0.1101P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1556 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(14)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3780
_refine_ls_number_parameters     295
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0803
_refine_ls_wR_factor_gt          0.0783
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7418(6) 0.4594(3) 1.4575(3) 0.0219(6) Uani 1 1 d D . . . .
H1 H 0.791(8) 0.500(5) 1.372(3) 0.033 Uiso 1 1 d D U . . .
O2 O 0.5483(5) 0.6865(3) 1.4561(3) 0.0191(6) Uani 1 1 d . . . . .
O3 O -0.1710(6) 0.9433(3) 1.4958(3) 0.0217(6) Uani 1 1 d . . . . .
H3 H -0.252(9) 0.904(5) 1.583(4) 0.033 Uiso 1 1 d . U . . .
O4 O 0.0259(5) 0.7156(3) 1.5024(3) 0.0186(6) Uani 1 1 d . . . . .
O5 O -0.3798(5) 0.5357(3) 2.1335(3) 0.0204(6) Uani 1 1 d D . . . .
H5 H -0.508(6) 0.544(5) 2.094(5) 0.031 Uiso 1 1 d D U . . .
O6 O -0.1661(5) 0.5273(3) 1.9195(3) 0.0255(7) Uani 1 1 d . . . . .
O7 O 0.2359(5) 0.5459(3) 2.0202(2) 0.0184(6) Uani 1 1 d . . . . .
O8 O 0.0173(5) 0.5564(3) 2.2294(3) 0.0197(6) Uani 1 1 d . . . . .
O9 O 0.9472(5) 0.8745(3) 0.8241(3) 0.0200(6) Uani 1 1 d D . . . .
H9 H 1.061(7) 0.885(4) 0.866(5) 0.030 Uiso 1 1 d D U . . .
O10 O 0.7336(6) 0.8799(4) 1.0385(3) 0.0275(7) Uani 1 1 d . . . . .
O11 O 0.3284(5) 0.8744(3) 0.9364(3) 0.0183(6) Uani 1 1 d . . . . .
O12 O 0.5505(5) 0.8492(3) 0.7297(3) 0.0185(6) Uani 1 1 d . . . . .
N1 N 0.3223(6) 0.6100(3) 1.7220(3) 0.0173(7) Uani 1 1 d D . . . .
H1A H 0.203(7) 0.629(5) 1.676(5) 0.026 Uiso 1 1 d D U . . .
H1C H 0.385(9) 0.689(4) 1.714(5) 0.026 Uiso 1 1 d D U . . .
H1B H 0.274(8) 0.581(5) 1.812(3) 0.026 Uiso 1 1 d D U . . .
N2 N 0.2550(6) 0.7862(3) 1.2369(3) 0.0173(7) Uani 1 1 d D . . . .
H2A H 0.322(8) 0.817(5) 1.150(3) 0.026 Uiso 1 1 d D U . . .
H2B H 0.196(9) 0.704(4) 1.248(5) 0.026 Uiso 1 1 d D U . . .
H2C H 0.366(7) 0.761(5) 1.292(5) 0.026 Uiso 1 1 d D U . . .
C1 C 0.6024(7) 0.5587(4) 1.5158(4) 0.0158(7) Uani 1 1 d . . . . .
C2 C 0.5144(7) 0.4979(4) 1.6728(4) 0.0174(8) Uani 1 1 d . . . . .
H2 H 0.652417 0.487116 1.725721 0.021 Uiso 1 1 calc R U . . .
C3 C 0.4351(8) 0.3464(4) 1.7041(4) 0.0178(8) Uani 1 1 d . . . . .
H3A H 0.568833 0.283433 1.657741 0.021 Uiso 1 1 calc R U . . .
C4 C 0.2121(8) 0.3525(4) 1.6369(4) 0.0217(8) Uani 1 1 d . . . . .
H4A H 0.243691 0.399021 1.534145 0.026 Uiso 1 1 calc R U . . .
H4B H 0.075690 0.414642 1.680184 0.026 Uiso 1 1 calc R U . . .
C5 C 0.1400(9) 0.2018(4) 1.6553(5) 0.0299(10) Uani 1 1 d . . . . .
H5A H 0.282806 0.133761 1.630665 0.045 Uiso 1 1 calc R U . . .
H5B H 0.021170 0.209509 1.592814 0.045 Uiso 1 1 calc R U . . .
H5C H 0.069769 0.165485 1.754379 0.045 Uiso 1 1 calc R U . . .
C6 C 0.4054(6) 0.2750(3) 1.8634(3) 0.0283(6) Uani 1 1 d . . . . .
H6A H 0.547960 0.281438 1.902194 0.043 Uiso 1 1 calc R U . . .
H6B H 0.387331 0.172019 1.878620 0.043 Uiso 1 1 calc R U . . .
H6C H 0.261997 0.325755 1.911589 0.043 Uiso 1 1 calc R U . . .
C7 C -0.0269(7) 0.8413(4) 1.4405(4) 0.0168(8) Uani 1 1 d . . . . .
C8 C 0.0620(8) 0.8995(4) 1.2833(4) 0.0176(8) Uani 1 1 d . . . . .
H8 H -0.075189 0.909859 1.229879 0.021 Uiso 1 1 calc R U . . .
C9 C 0.1476(8) 1.0482(4) 1.2482(4) 0.0213(8) Uani 1 1 d . . . . .
H9A H 0.010942 1.120774 1.275052 0.026 Uiso 1 1 calc R U . . .
H9B H 0.196780 1.078794 1.144191 0.026 Uiso 1 1 calc R U . . .
C10 C 0.3580(8) 1.0508(4) 1.3227(4) 0.0222(9) Uani 1 1 d . . . . .
H10A H 0.312410 1.016997 1.426731 0.027 Uiso 1 1 calc R U . . .
H10B H 0.498435 0.982316 1.292479 0.027 Uiso 1 1 calc R U . . .
C11 C 0.4283(10) 1.2035(5) 1.2886(5) 0.0294(10) Uani 1 1 d . . . . .
H11A H 0.479207 1.235756 1.186080 0.044 Uiso 1 1 calc R U . . .
H11B H 0.561410 1.201346 1.339400 0.044 Uiso 1 1 calc R U . . .
H11C H 0.289656 1.271487 1.318498 0.044 Uiso 1 1 calc R U . . .
C12 C -0.1820(7) 0.5343(4) 2.0419(4) 0.0150(8) Uani 1 1 d . . . . .
C13 C 0.0434(7) 0.5462(4) 2.1038(4) 0.0142(7) Uani 1 1 d . . . . .
C14 C 0.7484(7) 0.8761(4) 0.9160(4) 0.0155(8) Uani 1 1 d . . . . .
C15 C 0.5240(7) 0.8661(4) 0.8535(4) 0.0146(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.305(5) . ?
O1 H1 0.84(2) . ?
O2 C1 1.220(5) . ?
O3 C7 1.320(5) . ?
O3 H3 0.91(4) . ?
O4 C7 1.208(5) . ?
O5 C12 1.307(5) . ?
O5 H5 0.88(2) . ?
O6 C12 1.212(5) . ?
O7 C13 1.244(5) . ?
O8 C13 1.248(4) . ?
O9 C14 1.313(5) . ?
O9 H9 0.87(2) . ?
O10 C14 1.205(5) . ?
O11 C15 1.257(5) . ?
O12 C15 1.251(4) . ?
N1 C2 1.493(5) . ?
N1 H1A 0.86(2) . ?
N1 H1C 0.88(3) . ?
N1 H1B 0.86(2) . ?
N2 C8 1.494(5) . ?
N2 H2A 0.87(2) . ?
N2 H2B 0.88(2) . ?
N2 H2C 0.88(2) . ?
C1 C2 1.525(5) . ?
C2 C3 1.537(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.528(6) . ?
C3 C6 1.530(4) . ?
C3 H3A 1.0000 . ?
C4 C5 1.531(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.524(5) . ?
C8 C9 1.525(6) . ?
C8 H8 1.0000 . ?
C9 C10 1.528(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.524(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.558(5) . ?
C14 C15 1.551(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 108(3) . . ?
C7 O3 H3 112(3) . . ?
C12 O5 H5 112(3) . . ?
C14 O9 H9 107(3) . . ?
C2 N1 H1A 112(3) . . ?
C2 N1 H1C 109(3) . . ?
H1A N1 H1C 111(4) . . ?
C2 N1 H1B 110(3) . . ?
H1A N1 H1B 110(5) . . ?
H1C N1 H1B 105(4) . . ?
C8 N2 H2A 112(3) . . ?
C8 N2 H2B 110(3) . . ?
H2A N2 H2B 111(4) . . ?
C8 N2 H2C 111(3) . . ?
H2A N2 H2C 109(4) . . ?
H2B N2 H2C 104(4) . . ?
O2 C1 O1 125.7(3) . . ?
O2 C1 C2 122.2(4) . . ?
O1 C1 C2 112.1(3) . . ?
N1 C2 C1 107.8(3) . . ?
N1 C2 C3 113.4(3) . . ?
C1 C2 C3 113.4(3) . . ?
N1 C2 H2 107.3 . . ?
C1 C2 H2 107.3 . . ?
C3 C2 H2 107.3 . . ?
C4 C3 C6 113.1(3) . . ?
C4 C3 C2 111.7(3) . . ?
C6 C3 C2 111.4(3) . . ?
C4 C3 H3A 106.7 . . ?
C6 C3 H3A 106.7 . . ?
C2 C3 H3A 106.7 . . ?
C3 C4 C5 113.2(3) . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.8 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O4 C7 O3 125.8(3) . . ?
O4 C7 C8 122.6(3) . . ?
O3 C7 C8 111.6(3) . . ?
N2 C8 C7 107.6(3) . . ?
N2 C8 C9 111.7(3) . . ?
C7 C8 C9 114.2(3) . . ?
N2 C8 H8 107.7 . . ?
C7 C8 H8 107.7 . . ?
C9 C8 H8 107.7 . . ?
C8 C9 C10 114.1(3) . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
C10 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C9 111.7(3) . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O6 C12 O5 125.8(4) . . ?
O6 C12 C13 120.9(4) . . ?
O5 C12 C13 113.2(3) . . ?
O7 C13 O8 125.8(4) . . ?
O7 C13 C12 115.5(3) . . ?
O8 C13 C12 118.7(3) . . ?
O10 C14 O9 125.7(4) . . ?
O10 C14 C15 121.1(4) . . ?
O9 C14 C15 113.1(3) . . ?
O12 C15 O11 126.1(4) . . ?
O12 C15 C14 119.1(3) . . ?
O11 C15 C14 114.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 N1 11.7(5) . . . . ?
O1 C1 C2 N1 -169.5(3) . . . . ?
O2 C1 C2 C3 138.1(4) . . . . ?
O1 C1 C2 C3 -43.1(5) . . . . ?
N1 C2 C3 C4 57.5(4) . . . . ?
C1 C2 C3 C4 -65.9(4) . . . . ?
N1 C2 C3 C6 -70.0(4) . . . . ?
C1 C2 C3 C6 166.6(3) . . . . ?
C6 C3 C4 C5 -58.2(4) . . . . ?
C2 C3 C4 C5 175.2(4) . . . . ?
O4 C7 C8 N2 -11.8(5) . . . . ?
O3 C7 C8 N2 170.3(3) . . . . ?
O4 C7 C8 C9 -136.5(4) . . . . ?
O3 C7 C8 C9 45.6(5) . . . . ?
N2 C8 C9 C10 -62.2(4) . . . . ?
C7 C8 C9 C10 60.3(5) . . . . ?
C8 C9 C10 C11 -177.5(4) . . . . ?
O6 C12 C13 O7 -0.9(5) . . . . ?
O5 C12 C13 O7 -179.8(3) . . . . ?
O6 C12 C13 O8 178.4(3) . . . . ?
O5 C12 C13 O8 -0.4(5) . . . . ?
O10 C14 C15 O12 -173.7(3) . . . . ?
O9 C14 C15 O12 4.1(5) . . . . ?
O10 C14 C15 O11 5.5(5) . . . . ?
O9 C14 C15 O11 -176.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O8 0.84(2) 1.77(3) 2.550(4) 153(5) 1_654 yes
O3 H3 O12 0.91(4) 1.69(4) 2.592(4) 169(4) 1_456 yes
O5 H5 O7 0.88(2) 1.75(3) 2.619(4) 175(4) 1_455 yes
O9 H9 O11 0.87(2) 1.77(3) 2.621(4) 168(4) 1_655 yes
N1 H1A O4 0.86(2) 2.06(3) 2.857(4) 156(4) . yes
N1 H1C O12 0.88(3) 2.00(3) 2.862(4) 169(4) 1_556 yes
N1 H1B O7 0.86(2) 1.97(3) 2.807(4) 163(4) . yes
N2 H2A O11 0.87(2) 2.03(3) 2.830(4) 154(4) . yes
N2 H2B O8 0.88(2) 1.95(3) 2.815(5) 164(4) 1_554 yes
N2 H2C O2 0.88(2) 1.99(3) 2.841(4) 165(5) . yes

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.040


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: H2O'
