# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_LVK175
_database_code_depnum_ccdc_archive 'CCDC 2175349'
loop_
_audit_author_name
_audit_author_address
'Yulia Nelyubina'
;AN Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2022-05-27 deposited with the CCDC.	2022-10-10 downloaded from the CCDC.
;
_audit_creation_date             2022-05-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'O4 S, 2(C2 H6 N O)'
_chemical_formula_sum            'C4 H12 N2 O6 S'
_chemical_formula_weight         216.22
_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'
S S 0.1246 0.1234 '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                   5.7797(4)
_cell_length_b                   6.3309(5)
_cell_length_c                   12.8187(10)
_cell_angle_alpha                76.647(2)
_cell_angle_beta                 78.320(2)
_cell_angle_gamma                74.621(2)
_cell_volume                     435.01(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1764
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.45
_cell_measurement_theta_min      3.30
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.879
_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0480 before and 0.0403 after correction.
The Ratio of minimum to maximum transmission is 0.9225.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5422
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_min         1.652
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1949
_reflns_number_total             2302
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.042
_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)+(0.0439P)²+0.1377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0912
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All O(H) groups
2.a Riding coordinates:
 O1(H1), N1(H1A), O2(H2), N2(H2C)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1B,H1C), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
;
_atom_sites_solution_hydrogens   mixed
_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
S1 S 0.76424(7) 0.22489(7) 0.75534(3) 0.00981(11) Uani 1 1 d . . . . .
O3 O 0.8338(2) 0.02665(19) 0.70586(10) 0.0141(3) Uani 1 1 d . . . . .
O4 O 0.9576(2) 0.3567(2) 0.71712(9) 0.0136(3) Uani 1 1 d . . . . .
O5 O 0.7262(2) 0.1768(2) 0.87365(9) 0.0140(3) Uani 1 1 d . . . . .
O6 O 0.5337(2) 0.36894(19) 0.71555(9) 0.0127(2) Uani 1 1 d . . . . .
O1 O 1.2272(2) 0.30821(19) 0.53293(9) 0.0131(2) Uani 1 1 d . . . . .
H1 H 1.1378 0.3350 0.5961 0.016 Uiso 1 1 d R U . . .
N1 N 1.4420(2) 0.1631(2) 0.56903(11) 0.0105(3) Uani 1 1 d . . . . .
H1A H 1.4764 0.2203 0.6182 0.013 Uiso 1 1 d R U . . .
C1 C 1.6410(3) 0.1673(3) 0.47434(13) 0.0118(3) Uani 1 1 d . . . . .
H1B H 1.7969 0.0802 0.4983 0.014 Uiso 1 1 calc R U . . .
H1C H 1.6558 0.3229 0.4450 0.014 Uiso 1 1 calc R U . . .
C2 C 1.5898(3) 0.0700(3) 0.38652(13) 0.0113(3) Uani 1 1 d . . . . .
H2A H 1.4406 0.1637 0.3585 0.014 Uiso 1 1 calc R U . . .
H2B H 1.7260 0.0686 0.3256 0.014 Uiso 1 1 calc R U . . .
O2 O 0.2391(2) 0.60605(19) 0.84893(9) 0.0133(2) Uani 1 1 d . . . . .
H2 H 0.3338 0.5353 0.8035 0.016 Uiso 1 1 d R U . . .
N2 N 0.0601(2) 0.4780(2) 0.88789(11) 0.0102(3) Uani 1 1 d . . . . .
H2C H 0.0163 0.4375 0.8374 0.012 Uiso 1 1 d R U . . .
C3 C -0.1703(3) 0.6308(3) 0.92745(13) 0.0114(3) Uani 1 1 d . . . . .
H3A H -0.3029 0.5502 0.9482 0.014 Uiso 1 1 calc R U . . .
H3B H -0.2149 0.7588 0.8685 0.014 Uiso 1 1 calc R U . . .
C4 C -0.1403(3) 0.7149(3) 1.02431(13) 0.0111(3) Uani 1 1 d . . . . .
H4A H -0.0183 0.8072 1.0020 0.013 Uiso 1 1 calc R U . . .
H4B H -0.2964 0.8092 1.0521 0.013 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
S1 O3 1.4614(12) . ?
S1 O4 1.5067(12) . ?
S1 O5 1.4588(12) . ?
S1 O6 1.5112(12) . ?
O1 H1 0.8938 . ?
O1 N1 1.4249(17) . ?
N1 H1A 0.8732 . ?
N1 C1 1.494(2) . ?
N1 C2 1.500(2) 2_856 ?
C1 H1B 0.9900 . ?
C1 H1C 0.9900 . ?
C1 C2 1.512(2) . ?
C2 N1 1.500(2) 2_856 ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
O2 H2 0.8373 . ?
O2 N2 1.4230(17) . ?
N2 H2C 0.8527 . ?
N2 C3 1.495(2) . ?
N2 C4 1.499(2) 2_567 ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.515(2) . ?
C4 N2 1.499(2) 2_567 ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 109.48(7) . . ?
O3 S1 O6 107.71(7) . . ?
O4 S1 O6 107.59(7) . . ?
O5 S1 O3 114.10(7) . . ?
O5 S1 O4 108.32(7) . . ?
O5 S1 O6 109.47(7) . . ?
N1 O1 H1 100.9 . . ?
O1 N1 H1A 106.8 . . ?
O1 N1 C1 107.31(12) . . ?
O1 N1 C2 111.92(12) . 2_856 ?
C1 N1 H1A 108.5 . . ?
C1 N1 C2 110.87(12) . 2_856 ?
C2 N1 H1A 111.2 2_856 . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
N1 C1 C2 110.62(13) . . ?
H1B C1 H1C 108.1 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C2 C1 110.07(13) 2_856 . ?
N1 C2 H2A 109.6 2_856 . ?
N1 C2 H2B 109.6 2_856 . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.2 . . ?
N2 O2 H2 102.3 . . ?
O2 N2 H2C 112.9 . . ?
O2 N2 C3 107.61(11) . . ?
O2 N2 C4 111.09(12) . 2_567 ?
C3 N2 H2C 100.8 . . ?
C3 N2 C4 111.58(12) . 2_567 ?
C4 N2 H2C 112.3 2_567 . ?
N2 C3 H3A 109.6 . . ?
N2 C3 H3B 109.6 . . ?
N2 C3 C4 110.48(13) . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
N2 C4 C3 110.10(13) 2_567 . ?
N2 C4 H4A 109.6 2_567 . ?
N2 C4 H4B 109.6 2_567 . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.2 . . ?

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 N1 C1 C2 -64.89(15) . . . . ?
N1 C1 C2 N1 -57.14(18) . . . 2_856 ?
C2 N1 C1 C2 57.60(18) 2_856 . . . ?
O2 N2 C3 C4 -64.94(15) . . . . ?
N2 C3 C4 N2 -56.31(18) . . . 2_567 ?
C4 N2 C3 C4 57.16(18) 2_567 . . . ?

_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_lvk519
_database_code_depnum_ccdc_archive 'CCDC 2176251'
loop_
_audit_author_name
_audit_author_address
'Nasyrova Darina'
;Zelinsky Institute of Organic Chemistry RAS
Russia
;
_audit_update_record             
;
2022-06-01 deposited with the CCDC.	2022-10-10 downloaded from the CCDC.
;
_audit_creation_date             2022-05-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H7 N O2, 0.5(C4 H10 N2 O2)'
_chemical_formula_sum            'C9 H12 N2 O3'
_chemical_formula_weight         196.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     LVK519
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.63990(10)
_cell_length_b                   8.49780(10)
_cell_length_c                   11.93370(10)
_cell_angle_alpha                90
_cell_angle_beta                 116.019(2)
_cell_angle_gamma                90
_cell_volume                     969.64(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11168
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.5780
_cell_measurement_theta_min      4.6420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.856
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.54a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12736
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.829
_diffrn_reflns_theta_min         4.654
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00 107.00   0.50    0.15    --  107.75-112.00-133.73  142
  2  ω     49.00  75.00   0.50    0.15    --  107.75-125.00-120.00   52
  3  ω     68.00 109.00   0.50    0.15    --  107.75-125.00 -60.00   82
  4  ω     36.00 105.00   0.50    0.15    --  107.75 -95.00   0.00  138
  5  ω     40.00  66.00   0.50    0.15    --  107.75 -95.00 -60.00   52
  6  ω     36.00 134.00   0.50    0.15    --  107.75 -87.00-108.98  196
  7  ω     37.00  62.00   0.50    0.15    --  107.75 -55.00-120.35   50
  8  ω     40.00  66.00   0.50    0.15    --  107.75 -77.00 -90.00   52
  9  ω     80.00 105.00   0.50    0.15    --  107.75 -77.00 -90.00   50
 10  ω     36.00 105.00   0.50    0.15    --  107.75 -77.00 -30.00  138
 11  ω     72.00 108.00   0.50    0.15    --  107.75 -78.00  75.36   72
 12  ω     73.00  99.00   0.50    0.15    --  107.75 -77.00 150.00   52
 13  ω     71.00  96.00   0.50    0.15    --  107.75 -77.00 120.00   50
 14  ω     36.00  71.00   0.50    0.15    --  107.75 -61.00 120.00   70
 15  ω     37.00  67.00   0.50    0.15    --  107.75 -77.00 120.00   60
 16  ω     36.00  71.00   0.50    0.15    --  107.75 -61.00 150.00   70
 17  ω     36.00 105.00   0.50    0.15    --  107.75 -77.00  90.00  138
 18  ω     36.00  89.00   0.50    0.15    --  107.75 -71.00  65.00  106
 19  ω     37.00  63.00   0.50    0.15    --  107.75 -61.00  90.00   52
 20  ω     45.00  71.00   0.50    0.15    --  107.75 -61.00  60.00   52
 21  ω     37.00  62.00   0.50    0.15    --  107.75 -77.00 -60.00   50
 22  ω     99.00 162.00   0.50    0.15    --  107.75  30.00 120.00  126
 23  ω     86.00 156.00   0.50    0.15    --  107.75  77.00  30.00  140
 24  ω    109.00 173.00   0.50    0.15    --  107.75  45.00   0.00  128
 25  ω    134.00 176.00   0.50    0.15    --  107.75  30.00 150.00   84
 26  ω     99.00 124.00   0.50    0.15    --  107.75  61.00 -60.00   50
 27  ω     97.00 178.00   0.50    0.15    --  107.75  45.00 -90.00  162
 28  ω     30.00 120.00   0.50    0.05    --   48.70  71.00-163.00  180
 29  ω     89.00 178.00   0.50    0.15    --  107.75  71.00-163.00  178
 30  ω     97.00 178.00   0.50    0.15    --  107.75  30.00-180.00  162
 31  ω     96.00 134.00   0.50    0.15    --  107.75 125.00-150.00   76
 32  ω    -68.00  24.00   0.50    0.05    --  -48.70  71.00-163.00  184
 33  ω    -89.00 -14.00   0.50    0.15    --  -86.25  71.00-163.00  150
 34  ω   -120.00 -73.00   0.50    0.05    --  -48.70-125.00-150.00   94
 35  ω   -120.00 -29.00   0.50    0.05    --  -48.70 -71.00  65.00  182
 36  ω    -22.00  68.00   0.50    0.05    --   48.70 -71.00  65.00  180
 37  ω    -25.00  26.00   0.50    0.05    --   48.70 -19.00 -90.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1369702000
_diffrn_orient_matrix_UB_12      0.0954746000
_diffrn_orient_matrix_UB_13      0.0554694000
_diffrn_orient_matrix_UB_21      0.0616757000
_diffrn_orient_matrix_UB_22      -0.1084777000
_diffrn_orient_matrix_UB_23      -0.0667300000
_diffrn_orient_matrix_UB_31      -0.0582605000
_diffrn_orient_matrix_UB_32      0.1094591000
_diffrn_orient_matrix_UB_33      -0.1144853000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2007
_reflns_number_total             2067
_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       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0081(11)
_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   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2067
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0674P)²+0.3667P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1184
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2C,H2D)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.78262(10) 0.49501(12) 0.26447(8) 0.0260(3) Uani 1 1 d . . . . .
H1 H 0.698(2) 0.536(3) 0.253(2) 0.048(6) Uiso 1 1 d . . . . .
N1 N 0.86741(10) 0.51560(12) 0.39628(9) 0.0197(3) Uani 1 1 d . . . . .
C1 C 0.92206(13) 0.36005(14) 0.44883(12) 0.0231(3) Uani 1 1 d . . . . .
H1A H 0.975646 0.314727 0.406562 0.028 Uiso 1 1 calc R U . . .
H1B H 0.843727 0.288067 0.435970 0.028 Uiso 1 1 calc R U . . .
O2 O 0.55546(9) 0.62731(11) 0.26854(8) 0.0230(2) Uani 1 1 d . . . . .
N2 N 0.17071(12) 0.99824(13) 0.46960(11) 0.0235(3) Uani 1 1 d . . . . .
H2A H 0.1079(19) 1.053(2) 0.4043(18) 0.032(4) Uiso 1 1 d . . . . .
H2B H 0.202(2) 1.043(2) 0.544(2) 0.041(5) Uiso 1 1 d . . . . .
C2 C 0.98342(13) 0.62162(15) 0.41232(12) 0.0228(3) Uani 1 1 d . . . . .
H2C H 0.946281 0.725538 0.374967 0.027 Uiso 1 1 calc R U . . .
H2D H 1.037234 0.577369 0.369888 0.027 Uiso 1 1 calc R U . . .
C3 C 0.27013(12) 0.91924(14) 0.44668(11) 0.0196(3) Uani 1 1 d . . . . .
O3 O 0.69242(9) 0.63546(12) 0.47378(8) 0.0255(3) Uani 1 1 d . . . . .
H3 H 0.759(3) 0.586(3) 0.449(2) 0.064(7) Uiso 1 1 d . . . . .
C4 C 0.39190(13) 0.86131(15) 0.54574(11) 0.0225(3) Uani 1 1 d . . . . .
H4 H 0.406757 0.878339 0.629326 0.027 Uiso 1 1 calc R U . . .
C5 C 0.48969(12) 0.78008(15) 0.52234(11) 0.0220(3) Uani 1 1 d . . . . .
H5 H 0.572523 0.743624 0.590219 0.026 Uiso 1 1 calc R U . . .
C6 C 0.46910(12) 0.75024(14) 0.40003(11) 0.0194(3) Uani 1 1 d . . . . .
C7 C 0.34739(12) 0.80667(15) 0.30120(11) 0.0215(3) Uani 1 1 d . . . . .
H7 H 0.331648 0.787024 0.217692 0.026 Uiso 1 1 calc R U . . .
C8 C 0.24995(13) 0.89072(15) 0.32410(12) 0.0219(3) Uani 1 1 d . . . . .
H8 H 0.168404 0.929625 0.256143 0.026 Uiso 1 1 calc R U . . .
C9 C 0.57454(12) 0.66597(14) 0.37506(11) 0.0193(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 H1 0.92(2) . ?
O1 N1 1.4400(13) . ?
N1 C1 1.4693(16) . ?
N1 C2 1.4713(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5229(17) 3_766 ?
O2 C9 1.2404(15) . ?
N2 H2A 0.903(19) . ?
N2 H2B 0.88(2) . ?
N2 C3 1.3778(16) . ?
C2 H2C 0.9900 . ?
C2 H2D 0.9900 . ?
C3 C4 1.4052(17) . ?
C3 C8 1.4033(17) . ?
O3 H3 0.98(3) . ?
O3 C9 1.3160(14) . ?
C4 H4 0.9500 . ?
C4 C5 1.3755(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.4008(17) . ?
C6 C7 1.3992(16) . ?
C6 C9 1.4675(17) . ?
C7 H7 0.9500 . ?
C7 C8 1.3815(18) . ?
C8 H8 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O1 H1 102.4(14) . . ?
O1 N1 C1 107.33(9) . . ?
O1 N1 C2 107.72(9) . . ?
C1 N1 C2 110.06(9) . . ?
N1 C1 H1A 109.9 . . ?
N1 C1 H1B 109.9 . . ?
N1 C1 C2 108.74(10) . 3_766 ?
H1A C1 H1B 108.3 . . ?
C2 C1 H1A 109.9 3_766 . ?
C2 C1 H1B 109.9 3_766 . ?
H2A N2 H2B 117.0(18) . . ?
C3 N2 H2A 115.1(12) . . ?
C3 N2 H2B 115.1(13) . . ?
N1 C2 C1 108.67(10) . 3_766 ?
N1 C2 H2C 110.0 . . ?
N1 C2 H2D 110.0 . . ?
C1 C2 H2C 110.0 3_766 . ?
C1 C2 H2D 110.0 3_766 . ?
H2C C2 H2D 108.3 . . ?
N2 C3 C4 120.57(11) . . ?
N2 C3 C8 120.75(11) . . ?
C8 C3 C4 118.65(11) . . ?
C9 O3 H3 110.3(14) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.36(11) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.06(11) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C9 121.05(11) . . ?
C7 C6 C5 118.70(11) . . ?
C7 C6 C9 120.22(11) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.51(11) . . ?
C8 C7 H7 119.7 . . ?
C3 C8 H8 119.6 . . ?
C7 C8 C3 120.71(11) . . ?
C7 C8 H8 119.6 . . ?
O2 C9 O3 121.90(11) . . ?
O2 C9 C6 122.78(11) . . ?
O3 C9 C6 115.32(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2 0.92(2) 1.78(2) 2.6853(13) 167(2) . yes
N2 H2A O2 0.903(19) 2.128(19) 3.0117(14) 166.0(17) 2 yes
N2 H2B O1 0.88(2) 2.41(2) 3.1824(14) 146.9(17) 4_576 yes
O3 H3 O1 0.98(3) 2.45(3) 3.2693(13) 141.7(19) . yes
O3 H3 N1 0.98(3) 1.65(3) 2.6212(14) 175(2) . 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 N1 C1 C2 178.03(9) . . . 3_766 ?
O1 N1 C2 C1 -177.75(9) . . . 3_766 ?
C1 N1 C2 C1 -61.03(14) . . . 3_766 ?
N2 C3 C4 C5 178.84(11) . . . . ?
N2 C3 C8 C7 -177.70(11) . . . . ?
C2 N1 C1 C2 61.07(14) . . . 3_766 ?
C3 C4 C5 C6 -1.41(19) . . . . ?
C4 C3 C8 C7 0.35(18) . . . . ?
C4 C5 C6 C7 0.86(19) . . . . ?
C4 C5 C6 C9 178.93(11) . . . . ?
C5 C6 C7 C8 0.29(18) . . . . ?
C5 C6 C9 O2 174.52(11) . . . . ?
C5 C6 C9 O3 -6.28(17) . . . . ?
C6 C7 C8 C3 -0.89(19) . . . . ?
C7 C6 C9 O2 -7.45(18) . . . . ?
C7 C6 C9 O3 171.76(11) . . . . ?
C8 C3 C4 C5 0.79(18) . . . . ?
C9 C6 C7 C8 -177.80(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.910
_oxdiff_exptl_absorpt_empirical_full_min 0.405
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH, 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_lvk520
_database_code_depnum_ccdc_archive 'CCDC 2176252'
loop_
_audit_author_name
_audit_author_address
'Nasyrova Darina'
;Zelinsky Instituteof Organic Chemistry RAS
Russia
;
_audit_update_record             
;
2022-06-01 deposited with the CCDC.	2022-10-10 downloaded from the CCDC.
;
_audit_creation_date             2022-05-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H12 N2 O2, C2 O4, 0.901(H2 O)'
_chemical_formula_sum            'C6 H13.80 N2 O6.90'
_chemical_formula_weight         224.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     LVK520
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.54180(10)
_cell_length_b                   9.76040(10)
_cell_length_c                   10.15310(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.0180(10)
_cell_angle_gamma                90
_cell_volume                     938.492(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11061
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.4690
_cell_measurement_theta_min      4.3940
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.275
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.54a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_unetI/netI     0.0095
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12301
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.832
_diffrn_reflns_theta_min         6.009
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     41.00 120.00   0.50    0.25    --  107.75-137.00 143.00  158
  2  ω     36.00 111.00   0.50    0.25    --  107.75-125.00  60.00  150
  3  ω     38.00 116.00   0.50    0.25    --  107.75-132.00 -39.00  156
  4  ω     37.00  79.00   0.50    0.25    --  107.75 -95.00-150.00   84
  5  ω     36.00 111.00   0.50    0.25    --  107.75-125.00-120.00  150
  6  ω     71.00 106.00   0.50    0.25    --  107.75-125.00 -90.00   70
  7  ω     36.00 106.00   0.50    0.25    --  107.75 -96.00 -22.64  140
  8  ω     36.00 105.00   0.50    0.25    --  107.75 -95.00 -60.00  138
  9  ω     38.00  99.00   0.50    0.15    --   48.70-132.00 -39.00  122
 10  ω     66.00  98.00   0.50    0.25    --  107.75 -95.00 120.00   64
 11  ω     39.00  66.00   0.50    0.25    --  107.75 -61.00  30.00   54
 12  ω     36.00 105.00   0.50    0.25    --  107.75 -77.00   0.00  138
 13  ω     36.00  71.00   0.50    0.25    --  107.75 -61.00 -30.00   70
 14  ω     36.00 105.00   0.50    0.25    --  107.75 -77.00 -90.00  138
 15  ω     36.00  98.00   0.50    0.25    --  107.75 -77.00-120.00  124
 16  ω     36.00  71.00   0.50    0.25    --  107.75 -61.00 -60.00   70
 17  ω     36.00  71.00   0.50    0.25    --  107.75 -61.00   0.00   70
 18  ω     36.00  71.00   0.50    0.25    --  107.75 -61.00  90.00   70
 19  ω     97.00 178.00   0.50    0.25    --  107.75  30.00 -30.00  162
 20  ω    127.00 153.00   0.50    0.25    --  107.75  45.00-180.00   52
 21  ω     97.00 178.00   0.50    0.25    --  107.75  45.00-150.00  162
 22  ω    126.00 154.00   0.50    0.25    --  107.75  45.00   0.00   56
 23  ω    108.00 173.00   0.50    0.25    --  107.75  30.00  60.00  130
 24  ω    107.00 151.00   0.50    0.25    --  107.75  61.00 120.00   88
 25  ω     91.00 178.00   0.50    0.25    --  107.75 132.00  28.00  174
 26  ω    130.00 156.00   0.50    0.25    --  107.75 125.00 -30.00   52
 27  ω     96.00 130.00   0.50    0.25    --  107.75 125.00-120.00   68
 28  ω    135.00 161.00   0.50    0.25    --  107.75 125.00-120.00   52
 29  ω    -26.00  26.00   0.50    0.15    --  -48.70  19.00-180.00  104
 30  ω    -91.00 -17.00   0.50    0.15    --  -48.70 132.00  28.00  148
 31  ω    -51.00 -14.00   0.50    0.25    --  -86.25  45.00-120.00   74
 32  ω   -120.00 -69.00   0.50    0.15    --  -48.70-132.00 -39.00  102
 33  ω   -158.00 -69.00   0.50    0.25    --  -86.25-132.00 -39.00  178
 34  ω   -120.00 -66.00   0.50    0.15    --  -48.70-137.00 143.00  108
 35  ω   -120.00 -27.00   0.50    0.15    --  -48.70 -77.00  60.00  186
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0160460000
_diffrn_orient_matrix_UB_12      -0.1570529000
_diffrn_orient_matrix_UB_13      -0.0018724000
_diffrn_orient_matrix_UB_21      -0.1594514000
_diffrn_orient_matrix_UB_22      0.0153643000
_diffrn_orient_matrix_UB_23      0.0076703000
_diffrn_orient_matrix_UB_31      -0.0277622000
_diffrn_orient_matrix_UB_32      0.0027398000
_diffrn_orient_matrix_UB_33      -0.1527198000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1967
_reflns_number_total             1990
_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       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         1990
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+0.4398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0921
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Others
 Sof(O7)=Sof(H7A)=Sof(H7B)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1B,H1C), C2(H2B,H2C), C3(H3A,H3B), C4(H4A,H4B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.62208(8) 0.90748(8) 1.09702(8) 0.0140(2) Uani 1 1 d . . . . .
H1 H 0.612(2) 0.876(2) 1.190(2) 0.052(6) Uiso 1 1 d . . . . .
O2 O 0.77548(8) 0.60014(8) 0.82786(8) 0.01389(19) Uani 1 1 d . . . . .
H2 H 0.789(2) 0.632(2) 0.743(2) 0.040(5) Uiso 1 1 d . . . . .
O3 O 0.57695(9) 0.71106(9) 0.56984(8) 0.0183(2) Uani 1 1 d . . . . .
O4 O 0.81155(8) 0.68231(8) 0.59460(8) 0.01452(19) Uani 1 1 d . . . . .
O5 O 0.58891(8) 0.83394(8) 0.33463(8) 0.01440(19) Uani 1 1 d . . . . .
O6 O 0.82241(9) 0.79828(10) 0.35606(8) 0.0210(2) Uani 1 1 d . . . . .
O7 O 0.44093(11) 0.50129(11) 0.69880(11) 0.0225(4) Uani 0.901(6) 1 d . . P A 1
H7A H 0.494(3) 0.553(3) 0.664(2) 0.042(6) Uiso 0.901(6) 1 d . . P A 1
H7B H 0.392(2) 0.556(2) 0.738(2) 0.039(6) Uiso 0.901(6) 1 d . . P A 1
N1 N 0.56992(10) 0.80553(10) 1.00418(9) 0.0119(2) Uani 1 1 d . . . . .
H1A H 0.476(2) 0.8034(17) 0.9979(17) 0.028(4) Uiso 1 1 d . . . . .
N2 N 0.82855(10) 0.70244(9) 0.91975(9) 0.0112(2) Uani 1 1 d . . . . .
H2A H 0.9231(18) 0.7040(16) 0.9252(15) 0.019(4) Uiso 1 1 d . . . . .
C1 C 0.77339(11) 0.84208(11) 0.88027(10) 0.0118(2) Uani 1 1 d . . . . .
H1B H 0.801374 0.866378 0.792480 0.014 Uiso 1 1 calc R U . . .
H1C H 0.815256 0.910463 0.945584 0.014 Uiso 1 1 calc R U . . .
C2 C 0.61410(11) 0.84581(11) 0.87367(10) 0.0124(2) Uani 1 1 d . . . . .
H2B H 0.579567 0.939350 0.850134 0.015 Uiso 1 1 calc R U . . .
H2C H 0.571840 0.782184 0.803913 0.015 Uiso 1 1 calc R U . . .
C3 C 0.62513(12) 0.66636(11) 1.04393(11) 0.0139(2) Uani 1 1 d . . . . .
H3A H 0.583322 0.597771 0.978805 0.017 Uiso 1 1 calc R U . . .
H3B H 0.597205 0.642283 1.131795 0.017 Uiso 1 1 calc R U . . .
C4 C 0.78470(12) 0.66280(12) 1.05049(10) 0.0133(2) Uani 1 1 d . . . . .
H4A H 0.826920 0.726832 1.119899 0.016 Uiso 1 1 calc R U . . .
H4B H 0.819413 0.569413 1.074457 0.016 Uiso 1 1 calc R U . . .
C5 C 0.69488(11) 0.72093(11) 0.53134(10) 0.0122(2) Uani 1 1 d . . . . .
C6 C 0.70429(12) 0.78936(11) 0.39497(11) 0.0129(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 H1 1.01(2) . ?
O1 N1 1.4183(12) . ?
O2 H2 0.93(2) . ?
O2 N2 1.4172(12) . ?
O3 C5 1.2393(14) . ?
O4 C5 1.2725(13) . ?
O5 C6 1.2696(14) . ?
O6 C6 1.2421(14) . ?
O7 H7A 0.82(3) . ?
O7 H7B 0.84(3) . ?
N1 H1A 0.889(19) . ?
N1 C2 1.4915(13) . ?
N1 C3 1.4945(14) . ?
N2 H2A 0.898(17) . ?
N2 C1 1.4980(13) . ?
N2 C4 1.4908(13) . ?
C1 H1B 0.9900 . ?
C1 H1C 0.9900 . ?
C1 C2 1.5136(15) . ?
C2 H2B 0.9900 . ?
C2 H2C 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5163(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5497(15) . ?

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
N1 O1 H1 110.1(13) . . ?
N2 O2 H2 107.1(12) . . ?
H7A O7 H7B 103(2) . . ?
O1 N1 H1A 109.4(11) . . ?
O1 N1 C2 106.93(8) . . ?
O1 N1 C3 112.01(8) . . ?
C2 N1 H1A 109.5(11) . . ?
C2 N1 C3 110.54(8) . . ?
C3 N1 H1A 108.4(11) . . ?
O2 N2 H2A 109.2(10) . . ?
O2 N2 C1 112.29(8) . . ?
O2 N2 C4 106.66(8) . . ?
C1 N2 H2A 108.6(10) . . ?
C4 N2 H2A 109.8(10) . . ?
C4 N2 C1 110.29(8) . . ?
N2 C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
N2 C1 C2 110.59(9) . . ?
H1B C1 H1C 108.1 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C2 C1 110.22(9) . . ?
N1 C2 H2B 109.6 . . ?
N1 C2 H2C 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C1 C2 H2C 109.6 . . ?
H2B C2 H2C 108.1 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
N1 C3 C4 110.58(9) . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
N2 C4 C3 110.15(9) . . ?
N2 C4 H4A 109.6 . . ?
N2 C4 H4B 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
O3 C5 O4 126.15(10) . . ?
O3 C5 C6 117.98(10) . . ?
O4 C5 C6 115.85(10) . . ?
O5 C6 C5 115.94(10) . . ?
O6 C6 O5 126.12(10) . . ?
O6 C6 C5 117.92(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 O5 1.01(2) 1.56(2) 2.5734(11) 176(2) 1_556 yes
O1 H1 O6 1.01(2) 2.57(2) 3.2371(11) 123.1(15) 1_556 yes
O2 H2 O3 0.93(2) 2.63(2) 3.2266(11) 122.3(15) . yes
O2 H2 O4 0.93(2) 1.63(2) 2.5632(11) 178.3(19) . yes
O7 H7A O3 0.82(3) 2.03(3) 2.8295(13) 164(2) . yes
O7 H7B O6 0.84(3) 2.02(3) 2.8454(14) 166(2) 4_576 yes
N1 H1A O4 0.889(19) 1.956(18) 2.7363(12) 145.6(15) 4_576 yes
N1 H1A O6 0.889(19) 2.167(18) 2.8281(13) 130.7(14) 4_576 yes
N2 H2A O3 0.898(17) 2.114(16) 2.7875(12) 131.1(13) 4_676 yes
N2 H2A O5 0.898(17) 1.960(17) 2.7512(12) 146.2(14) 4_676 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 N1 C2 C1 64.81(10) . . . . ?
O1 N1 C3 C4 -61.53(11) . . . . ?
O2 N2 C1 C2 60.86(11) . . . . ?
O2 N2 C4 C3 -64.46(10) . . . . ?
O3 C5 C6 O5 1.96(15) . . . . ?
O3 C5 C6 O6 -179.48(10) . . . . ?
O4 C5 C6 O5 -176.71(9) . . . . ?
O4 C5 C6 O6 1.84(15) . . . . ?
N1 C3 C4 N2 -57.71(11) . . . . ?
N2 C1 C2 N1 57.58(11) . . . . ?
C1 N2 C4 C3 57.73(11) . . . . ?
C2 N1 C3 C4 57.61(11) . . . . ?
C3 N1 C2 C1 -57.36(11) . . . . ?
C4 N2 C1 C2 -57.95(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.303
_oxdiff_exptl_absorpt_empirical_full_min 0.740
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH, H2O'
