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

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

data_201030c
_database_code_depnum_ccdc_archive 'CCDC 2159563'
loop_
_audit_author_name
_audit_author_address
'yingying Wang'
;School of Chemical Engineering and Technology, Zhengzhou University
China
;
_audit_update_record             
;
2022-07-07 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;
_audit_creation_date             2022-07-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H2 O5, 2(C2 H7 N)'
_chemical_formula_sum            'C10 H16 N2 O5'
_chemical_formula_weight         244.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5303(7)
_cell_length_b                   9.5146(8)
_cell_length_c                   9.5825(9)
_cell_angle_alpha                70.618(2)
_cell_angle_beta                 66.8640(10)
_cell_angle_gamma                66.6890(10)
_cell_volume                     567.02(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1363
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.052
_cell_measurement_theta_min      3.086
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.9718
_exptl_absorpt_correction_T_min  0.9641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2938
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.341
_diffrn_reflns_theta_min         2.363
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1567
_reflns_number_total             2041
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2041
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0877
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2446
_refine_ls_wR_factor_ref         0.2739
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All N(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), N2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.1777(3) 0.6099(3) 0.2961(3) 0.0319(6) Uani 1 1 d . . . . .
O2 O -0.0355(4) 0.8916(3) 0.1641(3) 0.0401(7) Uani 1 1 d . . . . .
O3 O -0.0341(4) 1.0015(3) 0.3366(3) 0.0373(7) Uani 1 1 d . . . . .
O4 O 0.3659(4) 0.3265(3) 0.2143(3) 0.0485(8) Uani 1 1 d . . . . .
O5 O 0.4326(5) 0.2178(3) 0.4370(4) 0.0617(9) Uani 1 1 d . . . . .
C1 C 0.0026(5) 0.8854(4) 0.2823(4) 0.0302(8) Uani 1 1 d . . . . .
C2 C 0.1031(5) 0.7321(4) 0.3675(4) 0.0315(8) Uani 1 1 d . . . . .
C3 C 0.1383(6) 0.6829(4) 0.5071(4) 0.0380(9) Uani 1 1 d . . . . .
H3 H 0.102546 0.744271 0.577589 0.046 Uiso 1 1 calc R U . . .
C4 C 0.2382(6) 0.5228(4) 0.5242(4) 0.0406(9) Uani 1 1 d . . . . .
H4 H 0.280302 0.456351 0.609149 0.049 Uiso 1 1 calc R U . . .
C5 C 0.2621(5) 0.4825(4) 0.3944(4) 0.0319(8) Uani 1 1 d . . . . .
C6 C 0.3596(5) 0.3317(4) 0.3442(4) 0.0384(9) Uani 1 1 d . . . . .
N1 N 0.7977(4) 0.2384(3) 0.0957(3) 0.0333(7) Uani 1 1 d . . . . .
H1A H 0.872039 0.204423 0.007950 0.050 Uiso 1 1 calc R U . . .
H1B H 0.671638 0.236277 0.120848 0.050 Uiso 1 1 calc R U . . .
H1C H 0.851342 0.176859 0.171332 0.050 Uiso 1 1 calc R U . . .
C7 C 0.7947(5) 0.3996(4) 0.0742(4) 0.0356(8) Uani 1 1 d . . . . .
H7A H 0.724159 0.432508 0.172669 0.043 Uiso 1 1 calc R U . . .
H7B H 0.719739 0.468440 0.001923 0.043 Uiso 1 1 calc R U . . .
C8 C 1.0025(5) 0.4161(4) 0.0144(4) 0.0378(9) Uani 1 1 d . . . . .
H8A H 1.075410 0.378754 -0.081672 0.045 Uiso 1 1 calc R U . . .
H8B H 1.075414 0.351199 0.089015 0.045 Uiso 1 1 calc R U . . .
N2 N 0.3528(4) 0.9794(3) 0.3588(3) 0.0383(8) Uani 1 1 d . . . . .
H2A H 0.366112 1.070308 0.352650 0.057 Uiso 1 1 calc R U . . .
H2B H 0.387860 0.910204 0.440043 0.057 Uiso 1 1 calc R U . . .
H2C H 0.224448 0.992666 0.370200 0.057 Uiso 1 1 calc R U . . .
C9 C 0.4860(5) 0.9210(4) 0.2152(4) 0.0370(9) Uani 1 1 d . . . . .
H9A H 0.478421 0.818374 0.225763 0.044 Uiso 1 1 calc R U . . .
H9B H 0.625137 0.909761 0.201839 0.044 Uiso 1 1 calc R U . . .
C10 C 0.4290(5) 1.0279(4) 0.0738(4) 0.0371(8) Uani 1 1 d . . . . .
H10A H 0.430323 1.131803 0.065965 0.044 Uiso 1 1 calc R U . . .
H10B H 0.292017 1.035241 0.085054 0.044 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.358(4) . ?
O1 C5 1.365(4) . ?
O2 C1 1.252(4) . ?
O3 C1 1.262(4) . ?
O4 C6 1.244(5) . ?
O5 C6 1.241(5) . ?
C1 C2 1.480(5) . ?
C2 C3 1.357(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.346(5) . ?
C5 C6 1.476(5) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C7 1.471(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.493(5) . ?
C8 C8 1.515(6) 2_765 ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N2 C9 1.480(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.501(5) . ?
C10 C10 1.512(7) 2_675 ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C5 105.9(3) . . ?
O2 C1 O3 125.5(3) . . ?
O2 C1 C2 119.4(3) . . ?
O3 C1 C2 115.1(3) . . ?
O1 C2 C1 116.1(3) . . ?
C3 C2 O1 110.1(3) . . ?
C3 C2 C1 133.8(3) . . ?
C2 C3 H3 126.6 . . ?
C2 C3 C4 106.7(3) . . ?
C4 C3 H3 126.6 . . ?
C3 C4 H4 126.6 . . ?
C5 C4 C3 106.9(3) . . ?
C5 C4 H4 126.6 . . ?
O1 C5 C6 117.7(3) . . ?
C4 C5 O1 110.3(3) . . ?
C4 C5 C6 132.0(3) . . ?
O4 C6 C5 119.3(3) . . ?
O5 C6 O4 124.6(4) . . ?
O5 C6 C5 116.1(4) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C7 N1 H1A 109.5 . . ?
C7 N1 H1B 109.5 . . ?
C7 N1 H1C 109.5 . . ?
N1 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
N1 C7 C8 112.7(3) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C7 C8 C8 112.2(3) . 2_765 ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C8 C8 H8A 109.2 2_765 . ?
C8 C8 H8B 109.2 2_765 . ?
H8A C8 H8B 107.9 . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C9 N2 H2A 109.5 . . ?
C9 N2 H2B 109.5 . . ?
C9 N2 H2C 109.5 . . ?
N2 C9 H9A 109.1 . . ?
N2 C9 H9B 109.1 . . ?
N2 C9 C10 112.5(3) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C9 C10 C10 112.5(4) . 2_675 ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C10 C10 H10A 109.1 2_675 . ?
C10 C10 H10B 109.1 2_675 . ?
H10A C10 H10B 107.8 . . ?

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
C3 H3 O3 0.93 2.61 3.475(4) 155.7 2_576 yes
N1 H1A O2 0.89 1.89 2.779(4) 173.3 2_665 yes
N1 H1B O4 0.89 2.04 2.853(4) 151.2 . yes
N1 H1C O2 0.89 2.52 2.971(4) 112.1 1_645 yes
N1 H1C O3 0.89 2.05 2.932(4) 169.0 1_645 yes
C7 H7B O4 0.97 2.43 3.354(4) 159.9 2_665 yes
N2 H2A O4 0.89 2.36 3.154(4) 149.3 1_565 yes
N2 H2A O5 0.89 2.12 2.937(5) 152.1 1_565 yes
N2 H2B O5 0.89 1.92 2.758(4) 155.7 2_666 yes
N2 H2C O3 0.89 2.06 2.924(4) 163.3 . yes
C9 H9B O2 0.97 2.38 3.348(4) 178.0 1_655 yes
C10 H10A O4 0.97 2.49 3.328(4) 145.1 1_565 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -0.3(4) . . . . ?
O1 C5 C6 O4 1.7(5) . . . . ?
O1 C5 C6 O5 -179.1(3) . . . . ?
O2 C1 C2 O1 10.4(4) . . . . ?
O2 C1 C2 C3 -169.0(4) . . . . ?
O3 C1 C2 O1 -168.3(3) . . . . ?
O3 C1 C2 C3 12.4(5) . . . . ?
C1 C2 C3 C4 179.1(3) . . . . ?
C2 O1 C5 C4 1.1(4) . . . . ?
C2 O1 C5 C6 -178.8(3) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C3 C4 C5 O1 -1.3(4) . . . . ?
C3 C4 C5 C6 178.6(3) . . . . ?
C4 C5 C6 O4 -178.1(4) . . . . ?
C4 C5 C6 O5 1.0(6) . . . . ?
C5 O1 C2 C1 -179.9(2) . . . . ?
C5 O1 C2 C3 -0.4(4) . . . . ?
N1 C7 C8 C8 177.3(4) . . . 2_765 ?
N2 C9 C10 C10 177.3(4) . . . 2_675 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_201114g
_database_code_depnum_ccdc_archive 'CCDC 2159562'
loop_
_audit_author_name
_audit_author_address
'yingying Wang'
;School of Chemical Engineering and Technology, Zhengzhou University
China
;
_audit_update_record             
;
2022-07-07 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;
_audit_creation_date             2022-07-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C2 H7 N), C6 H2 O5, H2 O'
_chemical_formula_sum            'C10 H18 N2 O6'
_chemical_formula_weight         262.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2019(8)
_cell_length_b                   9.8663(9)
_cell_length_c                   9.8663(8)
_cell_angle_alpha                71.2540(10)
_cell_angle_beta                 76.887(2)
_cell_angle_gamma                76.887(2)
_cell_volume                     637.49(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1014
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.907
_cell_measurement_theta_min      2.668
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.9669
_exptl_absorpt_correction_T_min  0.9562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0834
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3466
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.211
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1582
_reflns_number_total             2485
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-1997  (Sheldrick, 2008)'
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2485
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0766
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0866P)²+0.5134P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1842
_refine_ls_wR_factor_ref         0.2020
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
 At 1.5 times of:
  All N(H,H,H) groups
2. Restrained distances
 O6-H6B
 0.85 with sigma of 0.01
 H6B-H6A
 1.45 with sigma of 0.01
3.a Riding coordinates:
 O6(H6A)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
3.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), N2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
N1 N -0.1533(4) 0.9085(3) 0.8389(3) 0.0285(7) Uani 1 1 d . . . . .
H1A H -0.246638 0.985380 0.836014 0.043 Uiso 1 1 calc R U . . .
H1B H -0.050513 0.924765 0.863465 0.043 Uiso 1 1 calc R U . . .
H1C H -0.195091 0.830866 0.904290 0.043 Uiso 1 1 calc R U . . .
N2 N 0.0385(5) 0.7198(3) 1.1891(3) 0.0319(8) Uani 1 1 d . . . . .
H2A H 0.143477 0.743390 1.203002 0.048 Uiso 1 1 calc R U . . .
H2B H -0.034100 0.799320 1.142398 0.048 Uiso 1 1 calc R U . . .
H2C H 0.073566 0.657078 1.136524 0.048 Uiso 1 1 calc R U . . .
O1 O 0.2764(3) 0.7052(2) 0.9008(3) 0.0265(6) Uani 1 1 d . . . . .
O2 O 0.1543(4) 0.4656(3) 1.1029(3) 0.0355(7) Uani 1 1 d . . . . .
O3 O 0.2904(4) 0.3245(3) 0.9546(3) 0.0355(7) Uani 1 1 d . . . . .
O4 O 0.1901(4) 0.9950(3) 0.8838(3) 0.0338(7) Uani 1 1 d . . . . .
O5 O 0.4352(4) 1.0419(3) 0.6938(3) 0.0407(7) Uani 1 1 d . . . . .
O6 O 0.3984(4) 0.7864(4) 1.2196(4) 0.0496(9) Uani 1 1 d D . . . .
H6A H 0.489615 0.748675 1.164480 0.060 Uiso 1 1 d DR U . . .
C1 C 0.2488(5) 0.4456(4) 0.9858(4) 0.0260(8) Uani 1 1 d . . . . .
C2 C 0.3187(5) 0.5735(4) 0.8681(4) 0.0260(8) Uani 1 1 d . . . . .
C3 C 0.4229(5) 0.5907(4) 0.7318(4) 0.0304(9) Uani 1 1 d . . . . .
H3 H 0.468297 0.519222 0.684119 0.037 Uiso 1 1 calc R U . . .
C4 C 0.4501(5) 0.7407(4) 0.6748(4) 0.0303(9) Uani 1 1 d . . . . .
H4 H 0.515717 0.784276 0.583880 0.036 Uiso 1 1 calc R U . . .
C5 C 0.3597(5) 0.8059(4) 0.7817(4) 0.0246(8) Uani 1 1 d . . . . .
C6 C 0.3272(5) 0.9603(4) 0.7876(4) 0.0273(8) Uani 1 1 d . . . . .
C7 C -0.0984(5) 0.8822(4) 0.6922(4) 0.0273(8) Uani 1 1 d . . . . .
H7A H -0.209034 0.859862 0.667879 0.033 Uiso 1 1 calc R U . . .
H7B H 0.004239 0.798912 0.695543 0.033 Uiso 1 1 calc R U . . .
C8 C -0.0305(6) 1.0144(4) 0.5739(4) 0.0296(9) Uani 1 1 d . . . . .
H8A H -0.134452 1.096991 0.568530 0.036 Uiso 1 1 calc R U . . .
H8B H 0.077790 1.038479 0.599561 0.036 Uiso 1 1 calc R U . . .
C9 C -0.0752(5) 0.6518(4) 1.3330(4) 0.0322(9) Uani 1 1 d . . . . .
H9A H -0.175188 0.609186 1.318246 0.039 Uiso 1 1 calc R U . . .
H9B H -0.137270 0.725604 1.381685 0.039 Uiso 1 1 calc R U . . .
C10 C 0.0567(6) 0.5356(4) 1.4266(4) 0.0358(10) Uani 1 1 d . . . . .
H10A H 0.156295 0.578576 1.441417 0.043 Uiso 1 1 calc R U . . .
H10B H 0.119460 0.462425 1.377275 0.043 Uiso 1 1 calc R U . . .
H6B H 0.434(3) 0.833(4) 1.267(4) 0.046(13) Uiso 1 1 d 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
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C7 1.501(5) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N2 C9 1.498(5) . ?
O1 C2 1.390(4) . ?
O1 C5 1.389(4) . ?
O2 C1 1.251(4) . ?
O3 C1 1.283(4) . ?
O4 C6 1.274(4) . ?
O5 C6 1.260(4) . ?
O6 H6A 0.8501 . ?
O6 H6B 0.859(10) . ?
C1 C2 1.508(5) . ?
C2 C3 1.361(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.446(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(5) . ?
C5 C6 1.506(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.535(5) . ?
C8 C8 1.523(7) 2_576 ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.514(5) . ?
C10 C10 1.525(8) 2_568 ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C7 N1 H1A 109.5 . . ?
C7 N1 H1B 109.5 . . ?
C7 N1 H1C 109.5 . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C9 N2 H2A 109.5 . . ?
C9 N2 H2B 109.5 . . ?
C9 N2 H2C 109.5 . . ?
C5 O1 C2 107.3(3) . . ?
H6A O6 H6B 114.7 . . ?
O2 C1 O3 125.6(3) . . ?
O2 C1 C2 118.5(3) . . ?
O3 C1 C2 115.8(3) . . ?
O1 C2 C1 116.5(3) . . ?
C3 C2 O1 109.4(3) . . ?
C3 C2 C1 134.1(3) . . ?
C2 C3 H3 126.3 . . ?
C2 C3 C4 107.4(3) . . ?
C4 C3 H3 126.3 . . ?
C3 C4 H4 126.9 . . ?
C5 C4 C3 106.3(3) . . ?
C5 C4 H4 126.9 . . ?
O1 C5 C6 117.7(3) . . ?
C4 C5 O1 109.6(3) . . ?
C4 C5 C6 132.6(3) . . ?
O4 C6 C5 116.5(3) . . ?
O5 C6 O4 127.3(3) . . ?
O5 C6 C5 116.2(3) . . ?
N1 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
N1 C7 C8 111.9(3) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C8 C8 C7 111.6(4) 2_576 . ?
C8 C8 H8A 109.3 2_576 . ?
C8 C8 H8B 109.3 2_576 . ?
H8A C8 H8B 108.0 . . ?
N2 C9 H9A 109.6 . . ?
N2 C9 H9B 109.6 . . ?
N2 C9 C10 110.2(3) . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C9 C10 C10 111.0(4) . 2_568 ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C10 C10 H10A 109.4 2_568 . ?
C10 C10 H10B 109.4 2_568 . ?
H10A C10 H10B 108.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O6 0.89 2.22 3.074(4) 160.6 2_577 yes
N1 H1B O4 0.89 2.08 2.956(4) 169.0 . yes
N1 H1C O3 0.89 1.85 2.741(4) 177.1 2_567 yes
N2 H2A O6 0.89 2.03 2.915(4) 174.1 . yes
N2 H2B O4 0.89 2.05 2.877(4) 154.0 2_577 yes
N2 H2C O1 0.89 2.42 2.998(4) 123.4 . yes
N2 H2C O2 0.89 1.96 2.795(4) 156.0 . yes
O6 H6A O3 0.85 1.90 2.742(4) 174.1 2_667 yes
C10 H10B O2 0.97 2.65 3.369(5) 131.0 . yes
O6 H6B O5 0.859(10) 1.889(17) 2.712(4) 160(3) 2_677 yes

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
N1 C7 C8 C8 178.3(4) . . . 2_576 ?
N2 C9 C10 C10 -179.7(4) . . . 2_568 ?
O1 C2 C3 C4 0.5(4) . . . . ?
O1 C5 C6 O4 -16.4(5) . . . . ?
O1 C5 C6 O5 165.7(3) . . . . ?
O2 C1 C2 O1 1.7(5) . . . . ?
O2 C1 C2 C3 179.5(4) . . . . ?
O3 C1 C2 O1 -179.4(3) . . . . ?
O3 C1 C2 C3 -1.5(6) . . . . ?
C1 C2 C3 C4 -177.5(4) . . . . ?
C2 O1 C5 C4 1.0(4) . . . . ?
C2 O1 C5 C6 177.5(3) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 O1 -0.7(4) . . . . ?
C3 C4 C5 C6 -176.5(4) . . . . ?
C4 C5 C6 O4 159.2(4) . . . . ?
C4 C5 C6 O5 -18.8(6) . . . . ?
C5 O1 C2 C1 177.5(3) . . . . ?
C5 O1 C2 C3 -0.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_210519d
_database_code_depnum_ccdc_archive 'CCDC 2159561'
loop_
_audit_author_name
_audit_author_address
'yingying Wang'
;School of Chemical Engineering and Technology, Zhengzhou University
China
;
_audit_update_record             
;
2022-07-07 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;
_audit_creation_date             2022-07-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C2 H7 N), C6 H2 O5, H2 O'
_chemical_formula_sum            'C10 H18 N2 O6'
_chemical_formula_weight         262.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9385(6)
_cell_length_b                   9.2887(8)
_cell_length_c                   10.7058(9)
_cell_angle_alpha                83.234(3)
_cell_angle_beta                 74.443(2)
_cell_angle_gamma                84.182(3)
_cell_volume                     658.32(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1187
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.069
_cell_measurement_theta_min      2.256
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9784
_exptl_absorpt_correction_T_min  0.9627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3620
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.214
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1735
_reflns_number_total             2591
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-1997  (Sheldrick, 2008)'
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.050(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2591
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0673
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0781P)²+0.2879P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1665
_refine_ls_wR_factor_ref         0.1831
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All O(H,H) groups
 At 1.5 times of:
  All N(H,H,H) groups
2. Restrained distances
 C9-C10' = C9-C10
 1.53 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C10 \\sim C10': within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
Uanis(C10) \\sim Ueq, Uanis(C10') \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(H9BC)=Sof(H9BD)=Sof(C10')=Sof(H10C)=Sof(H10D)=1-FVAR(1)
 Sof(H9AA)=Sof(H9AB)=Sof(C10)=Sof(H10A)=Sof(H10B)=FVAR(1)
5.a Riding coordinates:
 O6(H6A,H6B)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9AA,H9AB), C10(H10A,H10B), C10'(H10C,H10D)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
5.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), N2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
N1 N -0.1887(4) 0.2964(3) 0.4200(2) 0.0392(6) Uani 1 1 d . . . . .
H1A H -0.227034 0.275339 0.505958 0.059 Uiso 1 1 calc R U . . .
H1B H -0.070586 0.249213 0.388150 0.059 Uiso 1 1 calc R U . . .
H1C H -0.279373 0.269305 0.384106 0.059 Uiso 1 1 calc R U . . .
N2 N 0.7056(4) 0.2286(3) 1.0263(2) 0.0511(8) Uani 1 1 d . . . . .
H2A H 0.628515 0.230852 1.107372 0.077 Uiso 1 1 calc R U . . .
H2B H 0.818220 0.173731 1.027055 0.077 Uiso 1 1 calc R U . . .
H2C H 0.640316 0.191274 0.978032 0.077 Uiso 1 1 calc R U . . .
O1 O 0.4434(3) 0.1841(2) 0.55140(17) 0.0350(5) Uani 1 1 d . . . . .
O2 O 0.5054(3) 0.2338(2) 0.29355(18) 0.0424(6) Uani 1 1 d . . . . .
O3 O 0.1953(3) 0.1687(3) 0.30221(19) 0.0454(6) Uani 1 1 d . . . . .
O4 O 0.6835(3) 0.2329(3) 0.6990(2) 0.0527(7) Uani 1 1 d . . . . .
O5 O 0.4728(3) 0.1343(3) 0.88111(19) 0.0591(7) Uani 1 1 d . . . . .
O6 O 0.1047(3) 0.1375(3) 1.0615(2) 0.0694(9) Uani 1 1 d . . . . .
H6A H 0.127186 0.146811 1.134270 0.083 Uiso 1 1 d R U . . .
H6B H 0.216106 0.136101 1.003820 0.083 Uiso 1 1 d R U . . .
C1 C 0.3353(4) 0.1866(3) 0.3530(3) 0.0339(7) Uani 1 1 d . . . . .
C2 C 0.2959(4) 0.1502(3) 0.4971(3) 0.0323(7) Uani 1 1 d . . . . .
C3 C 0.1416(4) 0.0956(3) 0.5947(3) 0.0362(7) Uani 1 1 d . . . . .
H3 H 0.023136 0.065568 0.584822 0.043 Uiso 1 1 calc R U . . .
C4 C 0.1964(4) 0.0936(3) 0.7141(3) 0.0376(7) Uani 1 1 d . . . . .
H4 H 0.121091 0.061514 0.796679 0.045 Uiso 1 1 calc R U . . .
C5 C 0.3812(4) 0.1479(3) 0.6838(3) 0.0346(7) Uani 1 1 d . . . . .
C6 C 0.5244(5) 0.1746(4) 0.7602(3) 0.0407(8) Uani 1 1 d . . . . .
C7 C -0.1700(5) 0.4573(4) 0.3894(3) 0.0511(9) Uani 1 1 d . . . . .
H7A H -0.292786 0.508290 0.435575 0.061 Uiso 1 1 calc R U . . .
H7B H -0.154865 0.482067 0.296880 0.061 Uiso 1 1 calc R U . . .
C8 C 0.0074(5) 0.5097(4) 0.4267(3) 0.0459(8) Uani 1 1 d . . . . .
H8A H 0.018345 0.611852 0.396342 0.055 Uiso 1 1 calc R U . . .
H8B H 0.129426 0.457029 0.381686 0.055 Uiso 1 1 calc R U . . .
C9 C 0.7558(6) 0.3810(4) 0.9696(4) 0.0640(11) Uani 1 1 d D . . . .
H9AA H 0.861900 0.374800 0.889811 0.077 Uiso 0.675(13) 1 calc R U P A 1
H9AB H 0.808480 0.425004 1.030193 0.077 Uiso 0.675(13) 1 calc R U P A 1
H9BC H 0.789(18) 0.361(13) 0.863(12) 0.077 Uiso 0.325(13) 1 d . U P A 2
H9BD H 0.871(19) 0.390(13) 1.008(12) 0.077 Uiso 0.325(13) 1 d . U P A 2
C10 C 0.5814(9) 0.4823(7) 0.9393(8) 0.068(2) Uani 0.675(13) 1 d D U P A 1
H10A H 0.633482 0.572155 0.892795 0.081 Uiso 0.675(13) 1 calc R U P A 1
H10B H 0.522805 0.436772 0.882578 0.081 Uiso 0.675(13) 1 calc R U P A 1
C10' C 0.593(2) 0.5019(14) 1.0186(19) 0.079(4) Uani 0.325(13) 1 d D U P A 2
H10C H 0.562259 0.495230 1.112876 0.095 Uiso 0.325(13) 1 calc R U P A 2
H10D H 0.646837 0.595326 0.985635 0.095 Uiso 0.325(13) 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
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C7 1.504(4) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N2 C9 1.509(5) . ?
O1 C2 1.383(3) . ?
O1 C5 1.378(3) . ?
O2 C1 1.275(3) . ?
O3 C1 1.267(3) . ?
O4 C6 1.262(4) . ?
O5 C6 1.268(3) . ?
O6 H6A 0.8501 . ?
O6 H6B 0.8500 . ?
C1 C2 1.496(4) . ?
C2 C3 1.371(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.426(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.369(4) . ?
C5 C6 1.500(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.530(5) . ?
C8 C8 1.536(6) 2_566 ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9AA 0.9700 . ?
C9 H9AB 0.9700 . ?
C9 H9BC 1.14(13) . ?
C9 H9BD 1.01(13) . ?
C9 C10 1.538(6) . ?
C9 C10' 1.543(9) . ?
C10 C10 1.521(15) 2_667 ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10' C10' 1.45(3) 2_667 ?
C10' H10C 0.9700 . ?
C10' H10D 0.9700 . ?

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
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C7 N1 H1A 109.5 . . ?
C7 N1 H1B 109.5 . . ?
C7 N1 H1C 109.5 . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C9 N2 H2A 109.5 . . ?
C9 N2 H2B 109.5 . . ?
C9 N2 H2C 109.5 . . ?
C5 O1 C2 107.7(2) . . ?
H6A O6 H6B 108.3 . . ?
O2 C1 C2 117.0(2) . . ?
O3 C1 O2 126.4(3) . . ?
O3 C1 C2 116.6(3) . . ?
O1 C2 C1 115.2(2) . . ?
C3 C2 O1 108.8(2) . . ?
C3 C2 C1 135.9(3) . . ?
C2 C3 H3 126.3 . . ?
C2 C3 C4 107.3(2) . . ?
C4 C3 H3 126.3 . . ?
C3 C4 H4 126.6 . . ?
C5 C4 C3 106.8(2) . . ?
C5 C4 H4 126.6 . . ?
O1 C5 C6 115.6(2) . . ?
C4 C5 O1 109.4(2) . . ?
C4 C5 C6 135.0(3) . . ?
O4 C6 O5 126.4(3) . . ?
O4 C6 C5 117.7(2) . . ?
O5 C6 C5 115.9(3) . . ?
N1 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
N1 C7 C8 113.2(3) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C7 C8 C8 114.5(3) . 2_566 ?
C7 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
C8 C8 H8A 108.6 2_566 . ?
C8 C8 H8B 108.6 2_566 . ?
H8A C8 H8B 107.6 . . ?
N2 C9 H9AA 108.3 . . ?
N2 C9 H9AB 108.3 . . ?
N2 C9 H9BC 97(6) . . ?
N2 C9 H9BD 99(7) . . ?
N2 C9 C10 115.9(4) . . ?
N2 C9 C10' 115.3(7) . . ?
H9AA C9 H9AB 107.4 . . ?
H9BC C9 H9BD 119(9) . . ?
C10 C9 H9AA 108.3 . . ?
C10 C9 H9AB 108.3 . . ?
C10' C9 H9BC 117(6) . . ?
C10' C9 H9BD 107(7) . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C10 C10 C9 113.0(7) 2_667 . ?
C10 C10 H10A 109.0 2_667 . ?
C10 C10 H10B 109.0 2_667 . ?
H10A C10 H10B 107.8 . . ?
C9 C10' H10C 108.5 . . ?
C9 C10' H10D 108.5 . . ?
C10' C10' C9 115.1(16) 2_667 . ?
C10' C10' H10C 108.5 2_667 . ?
C10' C10' H10D 108.5 2_667 . ?
H10C C10' H10D 107.5 . . ?

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
N1 H1A O4 0.89 2.00 2.885(3) 178.6 1_455 yes
N1 H1B O3 0.89 1.94 2.829(3) 172.4 . yes
N1 H1C O2 0.89 2.06 2.942(3) 172.8 1_455 yes
N2 H2A O2 0.89 1.95 2.829(3) 169.7 1_556 yes
N2 H2B O6 0.89 2.10 2.922(3) 152.2 1_655 yes
N2 H2C O5 0.89 1.90 2.783(4) 171.7 . yes
O6 H6A O3 0.85 2.01 2.864(3) 177.1 1_556 yes
O6 H6B O5 0.85 1.91 2.757(3) 177.1 . yes
C4 H4 O6 0.93 2.61 3.427(4) 146.5 2_557 yes
C8 H8A O4 0.97 2.55 3.295(4) 133.2 2_666 yes
C9 H9BC O4 1.14(13) 2.52(13) 3.520(5) 145(8) . yes

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
N1 C7 C8 C8 -64.1(5) . . . 2_566 ?
N2 C9 C10 C10 66.4(9) . . . 2_667 ?
N2 C9 C10' C10' -66(2) . . . 2_667 ?
O1 C2 C3 C4 -0.8(3) . . . . ?
O1 C5 C6 O4 3.0(4) . . . . ?
O1 C5 C6 O5 -176.4(3) . . . . ?
O2 C1 C2 O1 5.4(4) . . . . ?
O2 C1 C2 C3 -178.3(3) . . . . ?
O3 C1 C2 O1 -174.0(2) . . . . ?
O3 C1 C2 C3 2.2(5) . . . . ?
C1 C2 C3 C4 -177.2(3) . . . . ?
C2 O1 C5 C4 -0.7(3) . . . . ?
C2 O1 C5 C6 179.0(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 O1 0.2(3) . . . . ?
C3 C4 C5 C6 -179.4(3) . . . . ?
C4 C5 C6 O4 -177.3(3) . . . . ?
C4 C5 C6 O5 3.3(5) . . . . ?
C5 O1 C2 C1 178.2(2) . . . . ?
C5 O1 C2 C3 1.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
