# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_221126d
_database_code_depnum_ccdc_archive 'CCDC 2225395'
loop_
_audit_author_name
_audit_author_address
'qin yang'
;Shenzhen Institute of Advanced Technology
China
;
_audit_update_record             
;
2022-12-09 deposited with the CCDC.	2023-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H11 N O4'
_chemical_formula_sum            'C4 H11 N O4'
_chemical_formula_weight         137.14

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   5.8966(5)
_cell_length_b                   14.2652(11)
_cell_length_c                   7.4117(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.338(2)
_cell_angle_gamma                90.00
_cell_volume                     616.85(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      6.20
_cell_measurement_theta_max      78.99

_exptl_crystal_description       column
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    1.139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4550
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9343
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         6.03
_diffrn_reflns_theta_max         67.90
_reflns_number_total             2175
_reflns_number_gt                2162
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0522P)²+0.0844P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(15)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2175
_refine_ls_number_parameters     187
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0842
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.43822(18) 0.50823(8) 0.00138(15) 0.0153(3) Uani 1 1 d . . .
O1' O 0.71420(18) 0.35300(8) 0.03668(15) 0.0131(2) Uani 1 1 d . . .
H1'B H 0.8437 0.3745 -0.0086 0.020 Uiso 1 1 d R . .
H1'A H 0.5982 0.3988 0.0294 0.020 Uiso 1 1 d R . .
O2 O 0.14392(19) 0.40917(8) -0.04114(15) 0.0151(3) Uani 1 1 d . . .
O2' O 0.81690(18) 0.65864(8) 0.43124(14) 0.0130(3) Uani 1 1 d . . .
H2'A H 0.7032 0.6345 0.4708 0.019 Uiso 1 1 d R . .
H2'B H 0.9244 0.6181 0.4367 0.019 Uiso 1 1 d R . .
O3 O 0.19799(18) 0.64497(8) -0.19720(14) 0.0121(2) Uani 1 1 d . . .
H3A H 0.2743 0.6265 -0.2776 0.018 Uiso 1 1 calc R . .
O4 O 0.10507(19) 0.49860(8) 0.44213(15) 0.0143(3) Uani 1 1 d . . .
O5 O 0.41696(19) 0.58617(8) 0.52018(16) 0.0139(3) Uani 1 1 d . . .
O6 O 0.35312(18) 0.35743(8) 0.31471(14) 0.0120(2) Uani 1 1 d . . .
H6A H 0.3093 0.3736 0.2063 0.018 Uiso 1 1 calc R . .
N1 N -0.4015(2) 0.69296(10) 0.06155(18) 0.0129(3) Uani 1 1 d . . .
H1A H -0.496(4) 0.7405(18) 0.026(3) 0.024(6) Uiso 1 1 d . . .
H1B H -0.334(4) 0.6956(16) 0.174(3) 0.022(5) Uiso 1 1 d . . .
H1C H -0.496(5) 0.632(2) 0.052(4) 0.042(7) Uiso 1 1 d . . .
N2 N 0.9015(2) 0.32035(11) 0.42156(18) 0.0114(3) Uani 1 1 d . . .
H2A H 0.996(4) 0.3699(17) 0.435(3) 0.017(5) Uiso 1 1 d . . .
H2B H 1.014(4) 0.2759(16) 0.438(3) 0.017(5) Uiso 1 1 d . . .
H2C H 0.820(4) 0.3210(19) 0.318(4) 0.031(6) Uiso 1 1 d . . .
C1 C 0.2325(3) 0.48852(12) -0.0548(2) 0.0116(3) Uani 1 1 d . . .
C2 C 0.0761(3) 0.56846(11) -0.1362(2) 0.0111(3) Uani 1 1 d . . .
H2D H -0.0343 0.5437 -0.2406 0.013 Uiso 1 1 calc R . .
C3 C -0.0568(3) 0.60429(11) 0.0111(2) 0.0118(3) Uani 1 1 d . . .
H3B H 0.0522 0.6284 0.1149 0.014 Uiso 1 1 calc R . .
H3C H -0.1431 0.5518 0.0561 0.014 Uiso 1 1 calc R . .
C4 C -0.2230(3) 0.68189(11) -0.0605(2) 0.0137(3) Uani 1 1 d . . .
H4A H -0.1384 0.7416 -0.0658 0.016 Uiso 1 1 calc R . .
H4B H -0.2969 0.6663 -0.1854 0.016 Uiso 1 1 calc R . .
C5 C 0.3168(3) 0.51208(11) 0.4586(2) 0.0111(3) Uani 1 1 d . . .
C6 C 0.4730(3) 0.43242(11) 0.4102(2) 0.0105(3) Uani 1 1 d . . .
H6B H 0.5858 0.4584 0.3348 0.013 Uiso 1 1 calc R . .
C7 C 0.6030(3) 0.39286(12) 0.5874(2) 0.0123(3) Uani 1 1 d . . .
H7A H 0.7042 0.4424 0.6480 0.015 Uiso 1 1 calc R . .
H7B H 0.4910 0.3764 0.6696 0.015 Uiso 1 1 calc R . .
C8 C 0.7471(3) 0.30729(12) 0.5624(2) 0.0135(3) Uani 1 1 d . . .
H8A H 0.8412 0.2918 0.6803 0.016 Uiso 1 1 calc R . .
H8B H 0.6441 0.2535 0.5270 0.016 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.256(2) . ?
O1' H1'B 0.9292 . ?
O1' H1'A 0.9415 . ?
O2 C1 1.257(2) . ?
O2' H2'A 0.8433 . ?
O2' H2'B 0.8551 . ?
O3 C2 1.4165(19) . ?
O3 H3A 0.8400 . ?
O4 C5 1.252(2) . ?
O5 C5 1.263(2) . ?
O6 C6 1.4142(19) . ?
O6 H6A 0.8400 . ?
N1 C4 1.493(2) . ?
N1 H1A 0.89(3) . ?
N1 H1B 0.87(2) . ?
N1 H1C 1.02(3) . ?
N2 C8 1.493(2) . ?
N2 H2A 0.90(2) . ?
N2 H2B 0.91(3) . ?
N2 H2C 0.84(3) . ?
C1 C2 1.534(2) . ?
C2 C3 1.522(2) . ?
C2 H2D 1.0000 . ?
C3 C4 1.522(2) . ?
C3 H3B 0.9900 . ?
C3 H3C 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.538(2) . ?
C6 C7 1.530(2) . ?
C6 H6B 1.0000 . ?
C7 C8 1.514(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1'B O1' H1'A 112.3 . . ?
H2'A O2' H2'B 109.2 . . ?
C2 O3 H3A 109.5 . . ?
C6 O6 H6A 109.5 . . ?
C4 N1 H1A 111.6(16) . . ?
C4 N1 H1B 108.6(15) . . ?
H1A N1 H1B 115(2) . . ?
C4 N1 H1C 106.8(16) . . ?
H1A N1 H1C 108(2) . . ?
H1B N1 H1C 106(2) . . ?
C8 N2 H2A 116.9(14) . . ?
C8 N2 H2B 109.1(14) . . ?
H2A N2 H2B 96.0(18) . . ?
C8 N2 H2C 107.9(17) . . ?
H2A N2 H2C 111(2) . . ?
H2B N2 H2C 116(2) . . ?
O1 C1 O2 124.58(15) . . ?
O1 C1 C2 117.44(14) . . ?
O2 C1 C2 117.89(13) . . ?
O3 C2 C3 107.93(13) . . ?
O3 C2 C1 113.22(12) . . ?
C3 C2 C1 108.07(12) . . ?
O3 C2 H2D 109.2 . . ?
C3 C2 H2D 109.2 . . ?
C1 C2 H2D 109.2 . . ?
C2 C3 C4 111.51(12) . . ?
C2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3C 109.3 . . ?
C4 C3 H3C 109.3 . . ?
H3B C3 H3C 108.0 . . ?
N1 C4 C3 109.93(13) . . ?
N1 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
N1 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
O4 C5 O5 124.83(15) . . ?
O4 C5 C6 119.12(14) . . ?
O5 C5 C6 115.99(13) . . ?
O6 C6 C7 107.61(13) . . ?
O6 C6 C5 113.75(11) . . ?
C7 C6 C5 108.35(12) . . ?
O6 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C8 C7 C6 114.36(13) . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N2 C8 C7 113.27(13) . . ?
N2 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
N2 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O3 21.54(19) . . . . ?
O2 C1 C2 O3 -161.74(13) . . . . ?
O1 C1 C2 C3 -97.96(16) . . . . ?
O2 C1 C2 C3 78.76(17) . . . . ?
O3 C2 C3 C4 59.17(15) . . . . ?
C1 C2 C3 C4 -178.05(13) . . . . ?
C2 C3 C4 N1 161.05(13) . . . . ?
O4 C5 C6 O6 12.60(19) . . . . ?
O5 C5 C6 O6 -170.20(13) . . . . ?
O4 C5 C6 C7 -107.01(16) . . . . ?
O5 C5 C6 C7 70.18(17) . . . . ?
O6 C6 C7 C8 50.92(17) . . . . ?
C5 C6 C7 C8 174.32(13) . . . . ?
C6 C7 C8 N2 50.82(18) . . . . ?

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
O1' H1'B O2 0.93 1.89 2.7963(16) 165.4 1_655
O1' H1'A O1 0.94 1.82 2.7380(16) 164.0 .
O2' H2'A O5 0.84 1.91 2.7415(15) 170.0 .
O2' H2'B O4 0.86 2.01 2.8400(16) 164.5 1_655
O3 H3A O5 0.84 1.91 2.7464(16) 173.5 1_554
O6 H6A O2 0.84 2.01 2.8423(16) 169.1 .
N1 H1A O1' 0.89(3) 2.07(3) 2.9584(19) 176(2) 2
N1 H1B O2' 0.87(2) 2.05(2) 2.8953(17) 163(2) 1_455
N1 H1C O1 1.02(3) 1.84(3) 2.8131(18) 157(3) 1_455
N1 H1C O3 1.02(3) 2.39(3) 2.8999(17) 109(2) 1_455
N2 H2A O4 0.90(2) 1.94(2) 2.8065(19) 160.8(19) 1_655
N2 H2A O6 0.90(2) 2.41(2) 2.9341(16) 117.6(16) 1_655
N2 H2B O2' 0.91(3) 2.11(2) 2.9568(19) 154(2) 2_746
N2 H2C O1' 0.84(3) 2.14(3) 2.9430(18) 159(2) .

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        67.90
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.059
