# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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. 
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data_202305141_tw
_database_code_depnum_ccdc_archive 'CCDC 2292118'
loop_
_audit_author_name
_audit_author_address
'Jinqiu Fu'
;Zhengzhou University
China
;
_audit_update_record             
;
2023-11-10 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;
_audit_creation_date             2023-06-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H15 N3 O4'
_chemical_formula_sum            'C8 H15 N3 O4'
_chemical_formula_weight         217.23
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C13H9O1N1
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.0351(2)
_cell_length_b                   25.7114(10)
_cell_length_c                   8.6670(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.890(4)
_cell_angle_gamma                90
_cell_volume                     1073.63(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3246
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9230
_cell_measurement_theta_min      5.5760
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.803
_exptl_absorpt_coefficient_mu    0.918
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            3910
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.489
_diffrn_reflns_theta_min         3.438
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -12.00   0.80    4.50    --  -33.50 -37.00  60.00  115
  2  ω   -108.00 -36.00   0.80    4.50    --  -33.50 178.00-150.00   90
  3  ω    -56.00  36.00   0.80    4.50    --  -33.50  37.00-120.00  115
  4  ω   -108.00 -36.00   0.80    4.50    --  -33.50 178.00 -90.00   90
  5  ω    -71.00  38.60   0.80    4.50    --  -33.50  19.00   0.00  137
  6  ω     31.00  99.00   0.80    4.50    --   36.47-138.00 171.00   85
  7  ω     61.00 109.00   0.80    4.50    --   36.47 178.00 -30.00   60
  8  ω    -34.00  58.00   0.80    4.50    --   36.47 -37.00  60.00  115
  9  ω     40.00 128.00   0.80   15.00    --  108.00 -61.00 -90.00  110
 10  ω     88.00 176.00   0.80   15.00    --  108.00  61.00 -90.00  110
 11  ω     39.00 136.60   0.80   15.00    --  108.00 -77.00 150.00  122
 12  ω     38.00 106.00   0.80   15.00    --  108.00 -94.00 -60.00   85
 13  ω    104.00 176.00   0.80   15.00    --  108.00 111.00-180.00   90
 14  ω     88.00 177.60   0.80   15.00    --  108.00  45.00 -60.00  112
 15  ω     40.00 108.00   0.80   15.00    --  108.00-111.00 150.00   85
 16  ω     96.80 176.00   0.80   15.00    --  108.00  61.00-120.00   99
 17  ω     41.00 109.00   0.80   15.00    --  108.00 -30.00 120.00   85
 18  ω     77.00 103.40   0.80   15.00    --  108.00 -94.00 -30.00   33
 19  ω     38.00  98.00   0.80   15.00    --  108.00 -94.00-180.00   75
 20  ω     84.00 123.20   0.80   15.00    --  108.00 178.00-180.00   49
 21  ω     36.00 136.00   0.80   15.00    --  108.00 -15.00-120.00  125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0339065000
_diffrn_orient_matrix_UB_12      0.0553547000
_diffrn_orient_matrix_UB_13      0.0711632000
_diffrn_orient_matrix_UB_21      -0.1078020000
_diffrn_orient_matrix_UB_22      0.0228683000
_diffrn_orient_matrix_UB_23      -0.1711122000
_diffrn_orient_matrix_UB_31      -0.2991414000
_diffrn_orient_matrix_UB_32      -0.0019659000
_diffrn_orient_matrix_UB_33      0.0120984000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.933
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3576
_reflns_number_total             3910
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 _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 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 1456 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3910
_refine_ls_number_restraints     74
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      1.092
_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)+(0.0765P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1334
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.569(4)
 0.431(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups,
  All N(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C8'A-N3'A
 1.4 with sigma of 0.02
 C8'-N3'
 1.4 with sigma of 0.02
 C8A-N3A
 1.4 with sigma of 0.02
 N3-C8
 1.35 with sigma of 0.02
 C8-O4
 1.2 with sigma of 0.02
 O4A-C8A
 1.2 with sigma of 0.02
 C8'A-O4'A
 1.2 with sigma of 0.02
 C8-C7
 1.72 with sigma of 0.02
 C8A-C7
 1.64 with sigma of 0.02
 C7'-C8'
 1.7 with sigma of 0.02
 C6-C7
 1.65 with sigma of 0.02
 C8'A-C7'
 1.62 with sigma of 0.02
 C2'-C1'
 1.58 with sigma of 0.02
 C7'-C8' \\sim C4'-C5' \\sim C7'-C8'A \\sim C1'-C2' \\sim C4'-C6' \\sim C7'-C6'
 with sigma of 0.01
 C7-C8 \\sim C4-C5 \\sim C7-C8A \\sim C6-C7 \\sim C1-C2 \\sim C2-C3
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(N3A) \\sim Ueq, Uanis(N3) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C8A) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C7) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C8) = Uanis(C8A)
Uanis(N3) = Uanis(N3A)
Uanis(O4) = Uanis(O4A)
Uanis(O4') = Uanis(O4'A)
Uanis(C8') = Uanis(C8'A)
Uanis(N3') = Uanis(N3'A)
5. Others
 Sof(O4A)=Sof(N3A)=Sof(H3AA)=Sof(H3AB)=Sof(H7BC)=Sof(H7BD)=Sof(C8A)=1-FVAR(1)
 Sof(O4)=Sof(N3)=Sof(H3A)=Sof(H3B)=Sof(H7AA)=Sof(H7AB)=Sof(C8)=FVAR(1)
 Sof(O4'A)=Sof(N3'A)=Sof(H3'C)=Sof(H3'D)=Sof(H7'C)=Sof(H7'D)=Sof(C8'A)=1-FVAR(2)
 Sof(O4')=Sof(N3')=Sof(H3'A)=Sof(H3'B)=Sof(H7'A)=Sof(H7'B)=Sof(C8')=FVAR(2)
6.a Rotating group:
 N3'A(H3'C,H3'D)
6.b Ternary CH refined with riding coordinates:
 C2(H2A), C4(H4), C2'(H2'A), C4'(H4')
6.c Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7AA,H7AB), C7(H7BC,H7BD), C6'(H6'A,H6'B), C7'(H7'A,H7'B),
 C7'(H7'C,H7'D)
6.d Aromatic/amide H refined with riding coordinates:
 N2(H2)
6.e X=CH2 refined with riding coordinates:
 N3(H3A,H3B), N3A(H3AA,H3AB), N3'(H3'A,H3'B)
6.f Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C1(H1D,H1E,H1F), N1'(H1'A,H1'B,H1'C), C1'(H1'D,H1'E,H1'F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.1006(10) 0.6451(2) 0.2134(5) 0.0419(12) Uani 1 1 d . . . . .
O2 O 0.9496(10) 0.6663(2) 0.6248(6) 0.0465(13) Uani 1 1 d . . . . .
O3 O 0.7182(11) 0.6461(2) 0.7979(6) 0.0470(13) Uani 1 1 d . . . . .
O4 O 0.910(2) 0.4631(5) 0.556(2) 0.058(3) Uani 0.618(12) 1 d D . P A 1
O4A O 0.878(4) 0.4655(8) 0.461(3) 0.058(3) Uani 0.382(12) 1 d D . P A 2
N1 N 0.3079(13) 0.6407(3) -0.0538(7) 0.0387(13) Uani 1 1 d . . . . .
H1A H 0.3885 0.6464 -0.1310 0.046 Uiso 1 1 calc GR . . . .
H1B H 0.1286 0.6488 -0.0901 0.046 Uiso 1 1 calc GR . . . .
H1C H 0.3257 0.6073 -0.0258 0.046 Uiso 1 1 calc GR . . . .
N2 N 0.5428(11) 0.6502(2) 0.3688(6) 0.0320(11) Uani 1 1 d . . . . .
H2 H 0.7111 0.6566 0.3702 0.038 Uiso 1 1 calc R . . . .
N3 N 0.473(3) 0.4643(5) 0.566(2) 0.053(3) Uani 0.618(12) 1 d D U P A 1
H3A H 0.4705 0.4312 0.5799 0.064 Uiso 0.618(12) 1 calc R . P A 1
H3B H 0.3285 0.4826 0.5613 0.064 Uiso 0.618(12) 1 calc R . P A 1
N3A N 0.433(4) 0.4644(7) 0.462(3) 0.053(3) Uani 0.382(12) 1 d D U P A 2
H3AA H 0.4055 0.4329 0.4277 0.064 Uiso 0.382(12) 1 calc R . P A 2
H3AB H 0.3004 0.4818 0.4813 0.064 Uiso 0.382(12) 1 calc R . P A 2
C1 C 0.361(2) 0.7297(3) 0.0487(11) 0.064(3) Uani 1 1 d D . . . .
H1D H 0.4413 0.7418 -0.0326 0.096 Uiso 1 1 calc GR . . . .
H1E H 0.4285 0.7505 0.1441 0.096 Uiso 1 1 calc GR . . . .
H1F H 0.1628 0.7324 0.0096 0.096 Uiso 1 1 calc GR . . . .
C2 C 0.4423(15) 0.6733(3) 0.0883(7) 0.0359(15) Uani 1 1 d D . . . .
H2A H 0.6443 0.6696 0.1153 0.043 Uiso 1 1 calc R . . . .
C3 C 0.3431(12) 0.6546(3) 0.2294(7) 0.0287(13) Uani 1 1 d D . . . .
C4 C 0.4886(12) 0.6348(3) 0.5195(6) 0.0317(14) Uani 1 1 d D . . . .
H4 H 0.3239 0.6532 0.5298 0.038 Uiso 1 1 calc R . . . .
C5 C 0.7429(13) 0.6513(3) 0.6567(7) 0.0329(14) Uani 1 1 d D . . . .
C6 C 0.4438(13) 0.5765(3) 0.5252(7) 0.0354(13) Uani 1 1 d D . . . .
H6A H 0.2856 0.5667 0.4356 0.042 Uiso 1 1 calc R . . . .
H6B H 0.4000 0.5680 0.6241 0.042 Uiso 1 1 calc R . . . .
C7 C 0.6942(14) 0.5448(3) 0.5172(12) 0.051(2) Uani 1 1 d D U . . .
H7AA H 0.7155 0.5494 0.4104 0.061 Uiso 0.618(12) 1 calc R . P A 1
H7AB H 0.8567 0.5599 0.5931 0.061 Uiso 0.618(12) 1 calc R . P A 1
H7BC H 0.8357 0.5501 0.6192 0.061 Uiso 0.382(12) 1 calc R . P A 2
H7BD H 0.7632 0.5609 0.4352 0.061 Uiso 0.382(12) 1 calc R . P A 2
C8 C 0.699(3) 0.4868(4) 0.5507(19) 0.040(3) Uani 0.618(12) 1 d D U P A 1
C8A C 0.684(4) 0.4866(5) 0.485(3) 0.040(3) Uani 0.382(12) 1 d D U P A 2
O1' O 0.3769(11) 0.3575(3) 0.7100(6) 0.0477(14) Uani 1 1 d . . . . .
O2' O -0.0588(11) 0.3318(2) 1.1239(6) 0.0463(12) Uani 1 1 d . . . . .
O3' O 0.3441(11) 0.3535(3) 1.2952(6) 0.0484(13) Uani 1 1 d . . . . .
O4' O 0.344(4) 0.5340(7) 1.066(2) 0.061(4) Uani 0.65(3) 1 d . . P B 1
O4'A O 0.306(7) 0.5351(15) 0.994(5) 0.061(4) Uani 0.35(3) 1 d D . P B 2
N1' N -0.0877(12) 0.3585(2) 0.4423(6) 0.0354(12) Uani 1 1 d . . . . .
H1'A H -0.2335 0.3497 0.3603 0.042 Uiso 1 1 calc GR . . . .
H1'B H 0.0677 0.3524 0.4160 0.042 Uiso 1 1 calc GR . . . .
H1'C H -0.0975 0.3922 0.4641 0.042 Uiso 1 1 calc GR . . . .
N2' N 0.0856(11) 0.3514(2) 0.8652(6) 0.0337(12) Uani 1 1 d . . . . .
H2' H -0.079(15) 0.342(3) 0.873(8) 0.029(16) Uiso 1 1 d . . . . .
N3' N -0.081(3) 0.5402(6) 1.088(3) 0.062(4) Uani 0.65(3) 1 d D . P B 1
H3'A H -0.0573 0.5727 1.1110 0.074 Uiso 0.65(3) 1 calc R . P B 1
H3'B H -0.2358 0.5255 1.0837 0.074 Uiso 0.65(3) 1 calc R . P B 1
N3'A N -0.127(5) 0.5406(11) 0.998(5) 0.062(4) Uani 0.35(3) 1 d D . P B 2
H3'C H -0.2431 0.5386 0.9009 0.074 Uiso 0.35(3) 1 d GR . P B 2
H3'D H -0.2167 0.5302 1.0660 0.074 Uiso 0.35(3) 1 d GR . P B 2
C1' C -0.048(2) 0.2702(3) 0.5528(11) 0.067(3) Uani 1 1 d D . . . .
H1'D H -0.1800 0.2605 0.4526 0.101 Uiso 1 1 calc GR . . . .
H1'E H -0.0774 0.2494 0.6384 0.101 Uiso 1 1 calc GR . . . .
H1'F H 0.1364 0.2648 0.5461 0.101 Uiso 1 1 calc GR . . . .
C2' C -0.0873(13) 0.3273(3) 0.5866(7) 0.0328(13) Uani 1 1 d D . . . .
H2'A H -0.2639 0.3320 0.6111 0.039 Uiso 1 1 calc R . . . .
C3' C 0.1499(13) 0.3473(3) 0.7266(7) 0.0323(14) Uani 1 1 d . . . . .
C4' C 0.2880(13) 0.3666(2) 1.0161(6) 0.0301(13) Uani 1 1 d D . . . .
H4' H 0.4646 0.3492 1.0238 0.036 Uiso 1 1 calc R . . . .
C5' C 0.1811(14) 0.3479(3) 1.1552(7) 0.0315(13) Uani 1 1 d D . . . .
C6' C 0.3356(13) 0.4254(2) 1.0254(7) 0.0346(13) Uani 1 1 d D . . . .
H6'A H 0.4829 0.4336 1.1226 0.041 Uiso 1 1 calc R . . . .
H6'B H 0.3951 0.4365 0.9337 0.041 Uiso 1 1 calc R . . . .
C7' C 0.0751(15) 0.4550(3) 1.0264(11) 0.0480(19) Uani 1 1 d D . . . .
H7'A H 0.0009 0.4401 1.1080 0.058 Uiso 0.65(3) 1 calc R . P B 1
H7'B H -0.0630 0.4505 0.9227 0.058 Uiso 0.65(3) 1 calc R . P B 1
H7'C H 0.0378 0.4494 1.1288 0.058 Uiso 0.35(3) 1 calc R . P B 2
H7'D H -0.0812 0.4415 0.9419 0.058 Uiso 0.35(3) 1 calc R . P B 2
C8' C 0.123(3) 0.5128(4) 1.059(2) 0.040(4) Uani 0.65(3) 1 d D . P B 1
C8'A C 0.103(6) 0.5130(5) 1.001(4) 0.040(4) Uani 0.35(3) 1 d D . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.213(8) . ?
O2 C5 1.214(9) . ?
O3 C5 1.272(8) . ?
O4 C8 1.214(14) . ?
O4A C8A 1.19(2) . ?
N1 C2 1.480(9) . ?
N2 C3 1.333(8) . ?
N2 C4 1.464(8) . ?
N3 C8 1.314(15) . ?
N3A C8A 1.35(2) . ?
C1 C2 1.519(8) . ?
C2 C3 1.527(7) . ?
C4 C5 1.533(7) . ?
C4 C6 1.520(9) . ?
C6 C7 1.520(7) . ?
C7 C8 1.518(9) . ?
C7 C8A 1.520(10) . ?
O1' C3' 1.221(9) . ?
O2' C5' 1.230(9) . ?
O3' C5' 1.260(9) . ?
O4' C8' 1.227(18) . ?
O4'A C8'A 1.18(3) . ?
N1' C2' 1.486(8) . ?
N2' C3' 1.336(8) . ?
N2' C4' 1.459(8) . ?
N3' C8' 1.327(16) . ?
N3'A C8'A 1.35(2) . ?
C1' C2' 1.519(8) . ?
C2' C3' 1.524(8) . ?
C4' C5' 1.534(7) . ?
C4' C6' 1.530(7) . ?
C6' C7' 1.519(7) . ?
C7' C8' 1.519(9) . ?
C7' C8'A 1.521(10) . ?

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
C3 N2 C4 123.0(5) . . ?
N1 C2 C1 108.9(6) . . ?
N1 C2 C3 108.2(6) . . ?
C1 C2 C3 110.6(6) . . ?
O1 C3 N2 123.7(6) . . ?
O1 C3 C2 121.6(6) . . ?
N2 C3 C2 114.6(5) . . ?
N2 C4 C5 106.7(5) . . ?
N2 C4 C6 111.3(5) . . ?
C6 C4 C5 110.2(5) . . ?
O2 C5 O3 125.6(6) . . ?
O2 C5 C4 119.2(6) . . ?
O3 C5 C4 115.1(6) . . ?
C4 C6 C7 113.3(6) . . ?
C6 C7 C8A 123.5(9) . . ?
C8 C7 C6 119.0(7) . . ?
O4 C8 N3 123.2(11) . . ?
O4 C8 C7 117.7(10) . . ?
N3 C8 C7 119.0(10) . . ?
O4A C8A N3A 124.5(17) . . ?
O4A C8A C7 119.8(16) . . ?
N3A C8A C7 115.0(14) . . ?
C3' N2' C4' 122.6(5) . . ?
N1' C2' C1' 109.2(6) . . ?
N1' C2' C3' 107.3(5) . . ?
C1' C2' C3' 111.4(6) . . ?
O1' C3' N2' 124.7(6) . . ?
O1' C3' C2' 121.5(6) . . ?
N2' C3' C2' 113.8(6) . . ?
N2' C4' C5' 107.9(5) . . ?
N2' C4' C6' 111.7(5) . . ?
C6' C4' C5' 110.7(5) . . ?
O2' C5' O3' 125.1(6) . . ?
O2' C5' C4' 118.6(6) . . ?
O3' C5' C4' 116.2(6) . . ?
C7' C6' C4' 111.9(6) . . ?
C6' C7' C8' 113.6(8) . . ?
C6' C7' C8'A 112.0(12) . . ?
O4' C8' N3' 119.7(13) . . ?
O4' C8' C7' 122.5(13) . . ?
N3' C8' C7' 117.8(12) . . ?
O4'A C8'A N3'A 120(2) . . ?
O4'A C8'A C7' 126(3) . . ?
N3'A C8'A C7' 114(2) . . ?

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
N1 H1A O3 0.89 1.93 2.735(8) 149.5 1_554
N1 H1B O3 0.89 2.01 2.876(8) 163.0 1_454
N1 H1C O4' 0.89 2.04 2.92(2) 171.5 1_554
N1 H1C O4'A 0.89 1.87 2.75(4) 168.4 1_554
N1 H1C N3'A 0.89 2.91 3.49(3) 124.7 1_554
N2 H2 O1 0.86 2.71 3.452(7) 145.7 1_655
N3 H3A O1' 0.86 2.32 3.114(14) 152.9 .
N3 H3B O4 0.86 2.15 2.813(16) 133.2 1_455
N3A H3AA O3' 0.86 2.32 3.17(2) 170.0 1_554
N3A H3AB O4A 0.86 2.12 2.79(2) 134.2 1_455
N1' H1'A O3' 0.89 2.04 2.776(8) 139.6 1_454
N1' H1'B O3' 0.89 1.97 2.825(8) 160.5 1_554
N1' H1'C O4 0.89 1.99 2.864(15) 169.2 1_455
N1' H1'C O4A 0.89 1.89 2.76(2) 167.0 1_455
N2' H2' O1' 0.88(8) 2.72(7) 3.432(7) 138(5) 1_455
N3' H3'A O1 0.86 2.11 2.952(19) 164.2 1_556
N3' H3'B O4' 0.86 2.09 2.85(2) 147.7 1_455

_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 1.143
_oxdiff_exptl_absorpt_empirical_full_min 0.858
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.569(4)
2 0.431(4)

####################################################################### 
# 
# 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_35346_f1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2292119'
loop_
_audit_author_name
_audit_author_address
'Jinqiu Fu'
;Zhengzhou University
China
;
_audit_update_record             
;
2023-11-10 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;
_audit_creation_date             2022-10-13
_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         'C8 H15 N3 O4'
_chemical_formula_sum            'C8 H15 N3 O4'
_chemical_formula_weight         217.23
_chemical_absolute_configuration rm
_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 0.0181 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.0339(2)
_cell_length_b                   16.1821(8)
_cell_length_c                   16.2812(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1326.25(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      71.887
_cell_measurement_theta_min      3.852
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5220
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1820 before and 0.1077 after correction.
The Ratio of minimum to maximum transmission is 0.6927.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.088
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14722
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.327
_diffrn_reflns_theta_min         3.851
_diffrn_ambient_temperature      200.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2394
_reflns_number_total             2596
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 917 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.25(11)
_refine_ls_extinction_coef       0.0100(14)
_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   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2596
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.066
_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)+(0.0615P)²+0.1396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1062
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2
 0.9 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3D,H3E)
3.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
3.d Idealised Me refined as rotating group:
 N3(H3A,H3B,H3C), C8(H8A,H8B,H8C)
;
_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
O1 O 0.0688(3) 0.20001(10) 0.39094(13) 0.0481(5) Uani 1 1 d . . . . .
O2 O 0.4643(4) 0.49054(12) 0.24939(10) 0.0517(5) Uani 1 1 d . . . . .
O3 O 0.1722(3) 0.52925(13) 0.34245(11) 0.0534(5) Uani 1 1 d . . . . .
O4 O 0.8589(3) 0.47200(10) 0.53547(9) 0.0329(4) Uani 1 1 d . . . . .
N1 N 0.5096(3) 0.19137(12) 0.40107(14) 0.0412(5) Uani 1 1 d . . . . .
H1A H 0.500969 0.137348 0.406715 0.049 Uiso 1 1 calc R U . . .
H1B H 0.664744 0.216404 0.401603 0.049 Uiso 1 1 calc R U . . .
N2 N 0.4644(3) 0.48515(11) 0.46945(11) 0.0303(4) Uani 1 1 d D . . . .
H2 H 0.298(3) 0.5050(17) 0.4698(18) 0.051(8) Uiso 1 1 d D . . . .
N3 N 0.5658(4) 0.46085(13) 0.68166(11) 0.0378(5) Uani 1 1 d . . . . .
H3A H 0.564519 0.407477 0.664059 0.045 Uiso 1 1 calc R U . . .
H3B H 0.453094 0.466383 0.725017 0.045 Uiso 1 1 calc R U . . .
H3C H 0.733174 0.474939 0.697460 0.045 Uiso 1 1 calc R U . . .
C1 C 0.2899(4) 0.23479(14) 0.39180(14) 0.0329(5) Uani 1 1 d . . . . .
C2 C 0.3041(4) 0.32695(14) 0.38389(14) 0.0335(5) Uani 1 1 d . . . . .
H2A H 0.205204 0.351350 0.430518 0.040 Uiso 1 1 calc R U . . .
H2B H 0.209227 0.342817 0.333018 0.040 Uiso 1 1 calc R U . . .
C3 C 0.5790(4) 0.36671(13) 0.38154(13) 0.0297(5) Uani 1 1 d . . . . .
H3D H 0.667821 0.351974 0.329297 0.036 Uiso 1 1 calc R U . . .
H3E H 0.687727 0.344518 0.427158 0.036 Uiso 1 1 calc R U . . .
C4 C 0.5640(3) 0.46147(13) 0.38896(12) 0.0289(4) Uani 1 1 d . . . . .
H4 H 0.746861 0.484640 0.382079 0.035 Uiso 1 1 calc R U . . .
C5 C 0.3856(4) 0.49742(15) 0.32231(14) 0.0366(5) Uani 1 1 d . . . . .
C6 C 0.6186(4) 0.48859(13) 0.53610(13) 0.0299(4) Uani 1 1 d . . . . .
C7 C 0.4790(4) 0.51570(15) 0.61413(14) 0.0382(5) Uani 1 1 d . . . . .
H7 H 0.282448 0.510655 0.606687 0.046 Uiso 1 1 calc R U . . .
C8 C 0.5491(7) 0.60488(17) 0.63444(18) 0.0595(8) Uani 1 1 d . . . . .
H8A H 0.487449 0.641084 0.590120 0.089 Uiso 1 1 calc R U . . .
H8B H 0.742187 0.610130 0.640237 0.089 Uiso 1 1 calc R U . . .
H8C H 0.463001 0.620834 0.686033 0.089 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 C1 1.247(2) . ?
O2 C5 1.257(3) . ?
O3 C5 1.236(3) . ?
O4 C6 1.239(2) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C1 1.319(3) . ?
N2 H2 0.899(13) . ?
N2 C4 1.455(3) . ?
N2 C6 1.335(3) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
N3 C7 1.479(3) . ?
C1 C2 1.499(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.527(3) . ?
C3 H3D 0.9900 . ?
C3 H3E 0.9900 . ?
C3 C4 1.540(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.524(3) . ?
C6 C7 1.517(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.522(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
C4 N2 H2 115.0(19) . . ?
C6 N2 H2 121.5(19) . . ?
C6 N2 C4 122.86(16) . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C7 N3 H3A 109.5 . . ?
C7 N3 H3B 109.5 . . ?
C7 N3 H3C 109.5 . . ?
O1 C1 N1 120.6(2) . . ?
O1 C1 C2 119.38(19) . . ?
N1 C1 C2 120.01(17) . . ?
C1 C2 H2A 107.9 . . ?
C1 C2 H2B 107.9 . . ?
C1 C2 C3 117.70(17) . . ?
H2A C2 H2B 107.2 . . ?
C3 C2 H2A 107.9 . . ?
C3 C2 H2B 107.9 . . ?
C2 C3 H3D 109.2 . . ?
C2 C3 H3E 109.2 . . ?
C2 C3 C4 111.92(16) . . ?
H3D C3 H3E 107.9 . . ?
C4 C3 H3D 109.2 . . ?
C4 C3 H3E 109.2 . . ?
N2 C4 C3 110.48(16) . . ?
N2 C4 H4 108.6 . . ?
N2 C4 C5 109.74(16) . . ?
C3 C4 H4 108.6 . . ?
C5 C4 C3 110.67(17) . . ?
C5 C4 H4 108.6 . . ?
O2 C5 C4 116.9(2) . . ?
O3 C5 O2 124.2(2) . . ?
O3 C5 C4 118.9(2) . . ?
O4 C6 N2 123.49(19) . . ?
O4 C6 C7 121.47(18) . . ?
N2 C6 C7 115.04(17) . . ?
N3 C7 C6 108.18(17) . . ?
N3 C7 H7 109.5 . . ?
N3 C7 C8 109.8(2) . . ?
C6 C7 H7 109.5 . . ?
C6 C7 C8 110.4(2) . . ?
C8 C7 H7 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -177.4(2) . . . . ?
O4 C6 C7 N3 -44.8(3) . . . . ?
O4 C6 C7 C8 75.4(3) . . . . ?
N1 C1 C2 C3 3.8(3) . . . . ?
N2 C4 C5 O2 171.70(19) . . . . ?
N2 C4 C5 O3 -10.1(3) . . . . ?
N2 C6 C7 N3 135.96(19) . . . . ?
N2 C6 C7 C8 -103.9(2) . . . . ?
C1 C2 C3 C4 -169.75(18) . . . . ?
C2 C3 C4 N2 65.9(2) . . . . ?
C2 C3 C4 C5 -55.8(2) . . . . ?
C3 C4 C5 O2 -66.1(2) . . . . ?
C3 C4 C5 O3 112.1(2) . . . . ?
C4 N2 C6 O4 0.0(3) . . . . ?
C4 N2 C6 C7 179.21(18) . . . . ?
C6 N2 C4 C3 81.7(2) . . . . ?
C6 N2 C4 C5 -155.96(19) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.988 0.250 0.000 206.1 42.3 ?
2 -0.363 0.750 0.500 206.1 42.3 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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_r20230110a_autored
_database_code_depnum_ccdc_archive 'CCDC 2292123'
loop_
_audit_author_name
_audit_author_address
'Jinqiu Fu'
;Zhengzhou University
China
;
_audit_update_record             
;
2023-11-10 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;
_audit_creation_date             2023-01-12
_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         'C2 H6 O S, C8 H15 N3 O4'
_chemical_formula_sum            'C10 H21 N3 O5 S'
_chemical_formula_weight         295.36
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.94380(10)
_cell_length_b                   17.0476(3)
_cell_length_c                   8.7107(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.326(2)
_cell_angle_gamma                90
_cell_volume                     708.03(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7232
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      34.5380
_cell_measurement_theta_min      2.4130
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (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    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9712
_diffrn_reflns_point_group_measured_fraction_full 0.816
_diffrn_reflns_point_group_measured_fraction_max 0.665
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.676
_diffrn_reflns_theta_min         2.424
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50    0.50    --  -20.00   0.00   0.00  360
  2  ω   -110.00   7.00   0.50    0.50    --  -20.00 -70.00  90.00  234
  3  ω    -70.00   6.00   0.50    0.50    --  -20.00 -70.00 180.00  152
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'rigaku saturn 944+'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0660811000
_diffrn_orient_matrix_UB_12      0.0288663000
_diffrn_orient_matrix_UB_13      0.0560373000
_diffrn_orient_matrix_UB_21      0.0316020000
_diffrn_orient_matrix_UB_22      -0.0289700000
_diffrn_orient_matrix_UB_23      0.0605658000
_diffrn_orient_matrix_UB_31      0.1294904000
_diffrn_orient_matrix_UB_32      -0.0076656000
_diffrn_orient_matrix_UB_33      -0.0177956000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.415
_reflns_Friedel_fraction_full    0.634
_reflns_Friedel_fraction_max     0.400
_reflns_number_gt                3855
_reflns_number_total             4030
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 Flack x determined using 1082 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         4030
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.044
_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)+(0.0551P)²+0.0649P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0886
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups, All
  N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2)
2.d X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
2.e Idealised Me refined as rotating group:
 C1(H1D,H1E,H1F), C2(H2A,H2B,H2C), N1(H1A,H1B,H1C), C3(H3C,H3D,H3E)
;
_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
S1 S 0.23382(10) 0.39460(2) 0.70257(5) 0.01958(10) Uani 1 1 d . . . . .
O1 O 0.5107(3) 0.42240(9) 0.6786(2) 0.0291(3) Uani 1 1 d . . . . .
C1 C -0.0074(5) 0.39747(14) 0.5101(2) 0.0268(4) Uani 1 1 d . . . . .
H1D H -0.027714 0.451654 0.471109 0.040 Uiso 1 1 calc R U . . .
H1E H -0.190074 0.377652 0.516605 0.040 Uiso 1 1 calc R U . . .
H1F H 0.063071 0.364683 0.436644 0.040 Uiso 1 1 calc R U . . .
C2 C 0.2649(5) 0.29063(12) 0.7236(2) 0.0287(4) Uani 1 1 d . . . . .
H2A H 0.306347 0.268170 0.628712 0.043 Uiso 1 1 calc R U . . .
H2B H 0.088431 0.268792 0.735749 0.043 Uiso 1 1 calc R U . . .
H2C H 0.417142 0.277827 0.817721 0.043 Uiso 1 1 calc R U . . .
O2 O 0.7806(2) 0.59150(8) 0.46080(12) 0.0151(2) Uani 1 1 d . . . . .
O3 O -0.0528(2) 0.65095(7) 0.06058(12) 0.0132(2) Uani 1 1 d . . . . .
O4 O 0.1790(2) 0.61098(8) -0.11355(12) 0.0137(2) Uani 1 1 d . . . . .
O5 O 0.5144(3) 0.34309(8) 0.08864(17) 0.0198(2) Uani 1 1 d . . . . .
N1 N 0.6052(3) 0.58150(8) 0.73897(13) 0.0114(2) Uani 1 1 d . . . . .
H1A H 0.613693 0.529306 0.718861 0.014 Uiso 1 1 calc R U . . .
H1B H 0.530407 0.588565 0.822878 0.014 Uiso 1 1 calc R U . . .
H1C H 0.780961 0.602238 0.762595 0.014 Uiso 1 1 calc R U . . .
N2 N 0.3281(3) 0.59852(8) 0.31341(13) 0.0097(2) Uani 1 1 d . . . . .
H2 H 0.151717 0.603371 0.315148 0.012 Uiso 1 1 calc R U . . .
N3 N 0.0677(3) 0.31164(9) 0.07688(19) 0.0174(3) Uani 1 1 d . . . . .
H3A H 0.096845 0.261624 0.061992 0.021 Uiso 1 1 calc R U . . .
H3B H -0.099389 0.327749 0.080857 0.021 Uiso 1 1 calc R U . . .
C3 C 0.4364(5) 0.70948(11) 0.6232(2) 0.0217(4) Uani 1 1 d . . . . .
H3C H 0.374206 0.721527 0.718518 0.033 Uiso 1 1 calc R U . . .
H3D H 0.312597 0.735546 0.530774 0.033 Uiso 1 1 calc R U . . .
H3E H 0.628988 0.728209 0.637856 0.033 Uiso 1 1 calc R U . . .
C4 C 0.4263(3) 0.62132(9) 0.59626(15) 0.0102(2) Uani 1 1 d . . . . .
H4 H 0.228482 0.602819 0.578520 0.012 Uiso 1 1 calc R U . . .
C5 C 0.5290(3) 0.60102(9) 0.45054(15) 0.0093(2) Uani 1 1 d . . . . .
C6 C 0.3939(3) 0.58793(9) 0.16066(14) 0.0087(2) Uani 1 1 d . . . . .
H6 H 0.565194 0.619549 0.162722 0.010 Uiso 1 1 calc R U . . .
C7 C 0.1521(3) 0.61974(9) 0.02605(15) 0.0082(2) Uani 1 1 d . . . . .
C8 C 0.4582(3) 0.50198(9) 0.13285(16) 0.0105(2) Uani 1 1 d . . . . .
H8A H 0.523679 0.498338 0.035055 0.013 Uiso 1 1 calc R U . . .
H8B H 0.612451 0.483655 0.223088 0.013 Uiso 1 1 calc R U . . .
C9 C 0.2061(3) 0.44806(10) 0.1161(2) 0.0140(3) Uani 1 1 d . . . . .
H9A H 0.136965 0.452556 0.212499 0.017 Uiso 1 1 calc R U . . .
H9B H 0.053519 0.465130 0.023686 0.017 Uiso 1 1 calc R U . . .
C10 C 0.2774(3) 0.36315(10) 0.09344(18) 0.0126(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
S1 O1 1.5142(15) . ?
S1 C1 1.783(2) . ?
S1 C2 1.784(2) . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C1 H1F 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
O2 C5 1.2341(18) . ?
O3 C7 1.2492(18) . ?
O4 C7 1.2667(16) . ?
O5 C10 1.232(2) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C4 1.4856(18) . ?
N2 H2 0.8800 . ?
N2 C5 1.3371(17) . ?
N2 C6 1.4621(17) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N3 C10 1.337(2) . ?
C3 H3C 0.9800 . ?
C3 H3D 0.9800 . ?
C3 H3E 0.9800 . ?
C3 C4 1.520(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.5262(19) . ?
C6 H6 1.0000 . ?
C6 C7 1.5354(19) . ?
C6 C8 1.532(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.524(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.515(2) . ?

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
O1 S1 C1 105.42(10) . . ?
O1 S1 C2 105.57(10) . . ?
C1 S1 C2 98.15(11) . . ?
S1 C1 H1D 109.5 . . ?
S1 C1 H1E 109.5 . . ?
S1 C1 H1F 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
S1 C2 H2A 109.5 . . ?
S1 C2 H2B 109.5 . . ?
S1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C4 N1 H1A 109.5 . . ?
C4 N1 H1B 109.5 . . ?
C4 N1 H1C 109.5 . . ?
C5 N2 H2 119.1 . . ?
C5 N2 C6 121.70(12) . . ?
C6 N2 H2 119.1 . . ?
H3A N3 H3B 120.0 . . ?
C10 N3 H3A 120.0 . . ?
C10 N3 H3B 120.0 . . ?
H3C C3 H3D 109.5 . . ?
H3C C3 H3E 109.5 . . ?
H3D C3 H3E 109.5 . . ?
C4 C3 H3C 109.5 . . ?
C4 C3 H3D 109.5 . . ?
C4 C3 H3E 109.5 . . ?
N1 C4 C3 109.54(12) . . ?
N1 C4 H4 109.1 . . ?
N1 C4 C5 109.70(12) . . ?
C3 C4 H4 109.1 . . ?
C3 C4 C5 110.39(13) . . ?
C5 C4 H4 109.1 . . ?
O2 C5 N2 123.85(13) . . ?
O2 C5 C4 121.33(12) . . ?
N2 C5 C4 114.73(12) . . ?
N2 C6 H6 108.0 . . ?
N2 C6 C7 109.62(12) . . ?
N2 C6 C8 111.55(12) . . ?
C7 C6 H6 108.0 . . ?
C8 C6 H6 108.0 . . ?
C8 C6 C7 111.67(11) . . ?
O3 C7 O4 125.39(13) . . ?
O3 C7 C6 118.93(12) . . ?
O4 C7 C6 115.67(12) . . ?
C6 C8 H8A 108.9 . . ?
C6 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C6 113.16(12) . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C8 112.09(13) . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
O5 C10 N3 122.09(16) . . ?
O5 C10 C9 121.72(15) . . ?
N3 C10 C9 116.18(14) . . ?

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 C4 C5 O2 -34.6(2) . . . . ?
N1 C4 C5 N2 148.52(13) . . . . ?
N2 C6 C7 O3 2.21(19) . . . . ?
N2 C6 C7 O4 -177.20(13) . . . . ?
N2 C6 C8 C9 65.42(15) . . . . ?
C3 C4 C5 O2 86.15(19) . . . . ?
C3 C4 C5 N2 -90.69(16) . . . . ?
C5 N2 C6 C7 -157.27(13) . . . . ?
C5 N2 C6 C8 78.52(17) . . . . ?
C6 N2 C5 O2 -3.1(2) . . . . ?
C6 N2 C5 C4 173.61(14) . . . . ?
C6 C8 C9 C10 -178.35(12) . . . . ?
C7 C6 C8 C9 -57.63(16) . . . . ?
C8 C6 C7 O3 126.35(15) . . . . ?
C8 C6 C7 O4 -53.06(17) . . . . ?
C8 C9 C10 O5 -0.6(2) . . . . ?
C8 C9 C10 N3 -179.69(14) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.289
_oxdiff_exptl_absorpt_empirical_full_min 0.623
####################################################################### 
# 
# 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_r20230406b_autored
_database_code_depnum_ccdc_archive 'CCDC 2292120'
loop_
_audit_author_name
_audit_author_address
'Jinqiu Fu'
;Zhengzhou University
China
;
_audit_update_record             
;
2023-11-10 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;
_audit_creation_date             2023-04-07
_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(C8 H15 N3 O4)'
_chemical_formula_sum            'C16 H30 N6 O8'
_chemical_formula_weight         434.46
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.02400(10)
_cell_length_b                   8.6623(3)
_cell_length_c                   14.2346(9)
_cell_angle_alpha                96.682(4)
_cell_angle_beta                 95.901(4)
_cell_angle_gamma                106.738(3)
_cell_volume                     583.12(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4830
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      31.4340
_cell_measurement_theta_min      2.4730
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9754
_diffrn_reflns_point_group_measured_fraction_full 0.914
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.485
_diffrn_ambient_temperature      294.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_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   -110.00  70.00   0.50    2.00    --  -20.00   0.00  90.00  360
  2  ω   -110.00  55.00   0.50    2.00    --  -20.00   0.00 180.00  330
  3  ω   -110.00   7.00   0.50    2.00    --  -20.00 -70.00 180.00  234
  4  ω   -110.00   7.00   0.50    2.00    --  -20.00 -70.00   0.00  234
  5  ω   -110.00  -2.00   0.50    2.00    --  -20.00 -70.00  90.00  216
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn 944+'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0407743000
_diffrn_orient_matrix_UB_12      -0.0347775000
_diffrn_orient_matrix_UB_13      -0.0488742000
_diffrn_orient_matrix_UB_21      -0.0389247000
_diffrn_orient_matrix_UB_22      -0.0791176000
_diffrn_orient_matrix_UB_23      0.0131434000
_diffrn_orient_matrix_UB_31      -0.1378895000
_diffrn_orient_matrix_UB_32      0.0042369000
_diffrn_orient_matrix_UB_33      0.0028931000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.818
_reflns_Friedel_fraction_full    0.833
_reflns_Friedel_fraction_max     0.813
_reflns_number_gt                3808
_reflns_number_total             4307
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.760
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details 
;
 Flack x determined using 1382 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4307
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0771
_refine_ls_restrained_S_all      1.083
_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)+(0.1551P)²+0.0507P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2056
_refine_ls_wR_factor_ref         0.2189
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups, All
  N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2
 0.9 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C12(H12), C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3D,H3E), C10(H10A,H10B), C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 N5(H5)
3.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N4(H4A,H4B)
3.e Idealised Me refined as rotating group:
 N3(H3A,H3B,H3C), C8(H8A,H8B,H8C), N6(H6A,H6B,H6C), C16(H16A,H16B,H16C)
;
_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
O1 O 0.4728(10) 0.2750(8) 0.3969(3) 0.0644(14) Uani 1 1 d . . . . .
O2 O 0.1417(9) 0.0509(4) 0.7242(3) 0.0448(10) Uani 1 1 d . . . . .
O3 O 0.5542(8) 0.2359(5) 0.7776(4) 0.0501(11) Uani 1 1 d . . . . .
O4 O 0.0972(8) 0.6365(4) 0.7207(3) 0.0365(8) Uani 1 1 d . . . . .
N1 N 0.0377(11) 0.2893(9) 0.3984(4) 0.0585(16) Uani 1 1 d . . . . .
H1A H 0.009813 0.284716 0.337362 0.070 Uiso 1 1 calc R U . . .
H1B H -0.093057 0.296584 0.431616 0.070 Uiso 1 1 calc R U . . .
N2 N 0.3903(9) 0.4859(5) 0.7433(3) 0.0324(9) Uani 1 1 d D . . . .
H2 H 0.559(7) 0.482(8) 0.770(4) 0.043(17) Uiso 1 1 d D . . . .
N3 N 0.5747(9) 0.8959(5) 0.7118(3) 0.0356(10) Uani 1 1 d . . . . .
H3A H 0.565591 0.845869 0.652749 0.043 Uiso 1 1 calc R U . . .
H3B H 0.730284 0.980499 0.725853 0.043 Uiso 1 1 calc R U . . .
H3C H 0.425412 0.930797 0.715594 0.043 Uiso 1 1 calc R U . . .
C1 C 0.2780(12) 0.2853(8) 0.4405(4) 0.0438(13) Uani 1 1 d . . . . .
C2 C 0.3240(12) 0.2913(9) 0.5479(4) 0.0493(15) Uani 1 1 d . . . . .
H2A H 0.378446 0.196118 0.560440 0.059 Uiso 1 1 calc R U . . .
H2B H 0.483088 0.386209 0.573806 0.059 Uiso 1 1 calc R U . . .
C3 C 0.0871(10) 0.2978(6) 0.6041(4) 0.0312(10) Uani 1 1 d . . . . .
H3D H -0.063371 0.195615 0.586822 0.037 Uiso 1 1 calc R U . . .
H3E H 0.013957 0.384381 0.586888 0.037 Uiso 1 1 calc R U . . .
C4 C 0.1797(10) 0.3273(5) 0.7117(4) 0.0295(10) Uani 1 1 d . . . . .
H4 H 0.015313 0.323971 0.743898 0.035 Uiso 1 1 calc R U . . .
C5 C 0.3029(11) 0.1942(6) 0.7419(4) 0.0329(11) Uani 1 1 d . . . . .
C6 C 0.3289(9) 0.6260(5) 0.7448(3) 0.0247(9) Uani 1 1 d . . . . .
C7 C 0.5794(10) 0.7788(5) 0.7811(4) 0.0310(10) Uani 1 1 d . . . . .
H7 H 0.755035 0.750520 0.783351 0.037 Uiso 1 1 calc R U . . .
C8 C 0.5555(17) 0.8585(8) 0.8782(4) 0.0557(18) Uani 1 1 d . . . . .
H8A H 0.699631 0.961706 0.894809 0.084 Uiso 1 1 calc R U . . .
H8B H 0.577083 0.789488 0.924672 0.084 Uiso 1 1 calc R U . . .
H8C H 0.374591 0.875367 0.877142 0.084 Uiso 1 1 calc R U . . .
O5 O 0.5422(10) 0.7449(8) 0.5171(3) 0.0704(16) Uani 1 1 d . . . . .
O6 O 0.7222(9) 0.9562(4) 0.1935(3) 0.0462(10) Uani 1 1 d . . . . .
O7 O 0.9156(9) 0.7678(5) 0.1398(4) 0.0508(11) Uani 1 1 d . . . . .
O8 O 0.0981(7) 0.3701(4) 0.2006(3) 0.0371(9) Uani 1 1 d . . . . .
N4 N 0.9736(13) 0.7240(12) 0.5301(4) 0.081(2) Uani 1 1 d . . . . .
H4A H 0.985077 0.727964 0.591088 0.098 Uiso 1 1 calc R U . . .
H4B H 1.112499 0.714740 0.501672 0.098 Uiso 1 1 calc R U . . .
N5 N 0.5293(9) 0.5209(5) 0.1799(3) 0.0296(9) Uani 1 1 d . . . . .
H5 H 0.689161 0.518165 0.164506 0.036 Uiso 1 1 calc R U . . .
N6 N 0.3170(10) 0.1082(5) 0.2062(3) 0.0359(10) Uani 1 1 d . . . . .
H6A H 0.130638 0.067185 0.196300 0.043 Uiso 1 1 calc R U . . .
H6B H 0.373387 0.156395 0.266605 0.043 Uiso 1 1 calc R U . . .
H6C H 0.392857 0.028087 0.194649 0.043 Uiso 1 1 calc R U . . .
C9 C 0.7458(13) 0.7318(8) 0.4808(4) 0.0464(14) Uani 1 1 d . . . . .
C10 C 0.7571(12) 0.7223(9) 0.3738(4) 0.0466(14) Uani 1 1 d . . . . .
H10A H 0.902806 0.817083 0.362831 0.056 Uiso 1 1 calc R U . . .
H10B H 0.809403 0.626361 0.351691 0.056 Uiso 1 1 calc R U . . .
C11 C 0.4847(10) 0.7147(6) 0.3152(4) 0.0329(11) Uani 1 1 d . . . . .
H11A H 0.446628 0.817748 0.329876 0.039 Uiso 1 1 calc R U . . .
H11B H 0.333233 0.630041 0.332880 0.039 Uiso 1 1 calc R U . . .
C12 C 0.4898(10) 0.6795(5) 0.2078(3) 0.0286(10) Uani 1 1 d . . . . .
H12 H 0.310485 0.680334 0.173818 0.034 Uiso 1 1 calc R U . . .
C13 C 0.7283(10) 0.8101(6) 0.1764(4) 0.0319(10) Uani 1 1 d . . . . .
C14 C 0.3292(10) 0.3806(5) 0.1773(3) 0.0273(9) Uani 1 1 d . . . . .
C15 C 0.4074(11) 0.2300(6) 0.1411(4) 0.0354(11) Uani 1 1 d . . . . .
H15 H 0.611060 0.258225 0.141572 0.043 Uiso 1 1 calc R U . . .
C16 C 0.257(2) 0.1553(9) 0.0407(5) 0.063(2) Uani 1 1 d . . . . .
H16A H 0.303417 0.234677 -0.001570 0.095 Uiso 1 1 calc R U . . .
H16B H 0.057538 0.121608 0.041414 0.095 Uiso 1 1 calc R U . . .
H16C H 0.314189 0.062396 0.018760 0.095 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 C1 1.230(8) . ?
O2 C5 1.252(6) . ?
O3 C5 1.243(7) . ?
O4 C6 1.212(6) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.304(8) . ?
N2 H2 0.902(14) . ?
N2 C4 1.460(6) . ?
N2 C6 1.333(6) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 H3C 0.8900 . ?
N3 C7 1.498(7) . ?
C1 C2 1.514(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.511(8) . ?
C3 H3D 0.9700 . ?
C3 H3E 0.9700 . ?
C3 C4 1.524(7) . ?
C4 H4 0.9800 . ?
C4 C5 1.539(7) . ?
C6 C7 1.533(6) . ?
C7 H7 0.9800 . ?
C7 C8 1.504(8) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
O5 C9 1.220(8) . ?
O6 C13 1.271(6) . ?
O7 C13 1.243(7) . ?
O8 C14 1.222(6) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C9 1.303(9) . ?
N5 H5 0.8600 . ?
N5 C12 1.459(6) . ?
N5 C14 1.329(6) . ?
N6 H6A 0.8900 . ?
N6 H6B 0.8900 . ?
N6 H6C 0.8900 . ?
N6 C15 1.489(7) . ?
C9 C10 1.524(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.508(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.528(7) . ?
C12 H12 0.9800 . ?
C12 C13 1.537(7) . ?
C14 C15 1.517(7) . ?
C15 H15 0.9800 . ?
C15 C16 1.522(8) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
C4 N2 H2 115(4) . . ?
C6 N2 H2 122(4) . . ?
C6 N2 C4 122.6(4) . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C7 N3 H3A 109.5 . . ?
C7 N3 H3B 109.5 . . ?
C7 N3 H3C 109.5 . . ?
O1 C1 N1 123.0(6) . . ?
O1 C1 C2 117.3(5) . . ?
N1 C1 C2 119.7(5) . . ?
C1 C2 H2A 107.5 . . ?
C1 C2 H2B 107.5 . . ?
H2A C2 H2B 107.0 . . ?
C3 C2 C1 119.2(5) . . ?
C3 C2 H2A 107.5 . . ?
C3 C2 H2B 107.5 . . ?
C2 C3 H3D 109.1 . . ?
C2 C3 H3E 109.1 . . ?
C2 C3 C4 112.5(4) . . ?
H3D C3 H3E 107.8 . . ?
C4 C3 H3D 109.1 . . ?
C4 C3 H3E 109.1 . . ?
N2 C4 C3 111.7(4) . . ?
N2 C4 H4 108.5 . . ?
N2 C4 C5 108.5(4) . . ?
C3 C4 H4 108.5 . . ?
C3 C4 C5 110.8(4) . . ?
C5 C4 H4 108.5 . . ?
O2 C5 C4 116.3(5) . . ?
O3 C5 O2 125.5(5) . . ?
O3 C5 C4 118.0(4) . . ?
O4 C6 N2 124.6(4) . . ?
O4 C6 C7 121.0(4) . . ?
N2 C6 C7 114.4(4) . . ?
N3 C7 C6 106.8(4) . . ?
N3 C7 H7 110.0 . . ?
N3 C7 C8 108.5(4) . . ?
C6 C7 H7 110.0 . . ?
C8 C7 C6 111.6(5) . . ?
C8 C7 H7 110.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
H4A N4 H4B 120.0 . . ?
C9 N4 H4A 120.0 . . ?
C9 N4 H4B 120.0 . . ?
C12 N5 H5 118.5 . . ?
C14 N5 H5 118.5 . . ?
C14 N5 C12 122.9(4) . . ?
H6A N6 H6B 109.5 . . ?
H6A N6 H6C 109.5 . . ?
H6B N6 H6C 109.5 . . ?
C15 N6 H6A 109.5 . . ?
C15 N6 H6B 109.5 . . ?
C15 N6 H6C 109.5 . . ?
O5 C9 N4 123.0(6) . . ?
O5 C9 C10 123.2(5) . . ?
N4 C9 C10 113.8(5) . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 C9 114.1(5) . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C10 C11 C12 112.6(4) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
N5 C12 C11 111.9(4) . . ?
N5 C12 H12 108.7 . . ?
N5 C12 C13 107.9(4) . . ?
C11 C12 H12 108.7 . . ?
C11 C12 C13 111.0(4) . . ?
C13 C12 H12 108.7 . . ?
O6 C13 C12 116.1(5) . . ?
O7 C13 O6 124.9(5) . . ?
O7 C13 C12 118.9(4) . . ?
O8 C14 N5 124.0(4) . . ?
O8 C14 C15 121.4(4) . . ?
N5 C14 C15 114.6(4) . . ?
N6 C15 C14 107.7(4) . . ?
N6 C15 H15 109.9 . . ?
N6 C15 C16 108.3(5) . . ?
C14 C15 H15 109.9 . . ?
C14 C15 C16 111.2(5) . . ?
C16 C15 H15 109.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -177.8(6) . . . . ?
O4 C6 C7 N3 -47.8(6) . . . . ?
O4 C6 C7 C8 70.6(6) . . . . ?
N1 C1 C2 C3 1.5(10) . . . . ?
N2 C4 C5 O2 176.4(4) . . . . ?
N2 C4 C5 O3 -6.6(7) . . . . ?
N2 C6 C7 N3 132.7(5) . . . . ?
N2 C6 C7 C8 -108.9(6) . . . . ?
C1 C2 C3 C4 -172.0(5) . . . . ?
C2 C3 C4 N2 63.5(6) . . . . ?
C2 C3 C4 C5 -57.7(6) . . . . ?
C3 C4 C5 O2 -60.5(6) . . . . ?
C3 C4 C5 O3 116.5(5) . . . . ?
C4 N2 C6 O4 0.1(8) . . . . ?
C4 N2 C6 C7 179.5(4) . . . . ?
C6 N2 C4 C3 71.1(6) . . . . ?
C6 N2 C4 C5 -166.4(4) . . . . ?
O5 C9 C10 C11 -5.4(10) . . . . ?
O8 C14 C15 N6 -45.9(6) . . . . ?
O8 C14 C15 C16 72.7(7) . . . . ?
N4 C9 C10 C11 174.3(7) . . . . ?
N5 C12 C13 O6 178.6(4) . . . . ?
N5 C12 C13 O7 -3.9(6) . . . . ?
N5 C14 C15 N6 134.9(4) . . . . ?
N5 C14 C15 C16 -106.6(6) . . . . ?
C9 C10 C11 C12 -171.4(5) . . . . ?
C10 C11 C12 N5 62.2(6) . . . . ?
C10 C11 C12 C13 -58.4(6) . . . . ?
C11 C12 C13 O6 -58.5(6) . . . . ?
C11 C12 C13 O7 119.0(5) . . . . ?
C12 N5 C14 O8 -2.5(7) . . . . ?
C12 N5 C14 C15 176.7(4) . . . . ?
C14 N5 C12 C11 72.9(6) . . . . ?
C14 N5 C12 C13 -164.7(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.639 0.508 0.961 66.8 15.2 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.430
_oxdiff_exptl_absorpt_empirical_full_min 0.518
####################################################################### 
# 
# 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_r20220706a
_database_code_depnum_ccdc_archive 'CCDC 2292122'
loop_
_audit_author_name
_audit_author_address
'Jinqiu Fu'
;Zhengzhou University
China
;
_audit_update_record             
;
2023-11-10 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;
_audit_creation_date             2022-07-09
_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         'C8 H15 N3 O4, C2 H6 O'
_chemical_formula_sum            'C10 H21 N3 O5'
_chemical_formula_weight         263.30
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.0660(5)
_cell_length_b                   16.1694(7)
_cell_length_c                   16.1972(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2636.3(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    11112
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.8970
_cell_measurement_theta_min      2.3680
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_unetI/netI     0.0688
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            35347
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.876
_diffrn_reflns_theta_min         1.780
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   2.00    2.00    --  -25.00  45.00   0.00   90
  2  ω   -115.00  45.00   2.00    2.00    --  -25.00  45.00  90.00   80
  3  ω   -115.00  25.00   2.00    2.00    --  -25.00  45.00 180.00   70
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn70'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0253842000
_diffrn_orient_matrix_UB_12      0.0030130000
_diffrn_orient_matrix_UB_13      -0.0407503000
_diffrn_orient_matrix_UB_21      0.0061358000
_diffrn_orient_matrix_UB_22      -0.0434363000
_diffrn_orient_matrix_UB_23      -0.0046755000
_diffrn_orient_matrix_UB_31      -0.0654527000
_diffrn_orient_matrix_UB_32      -0.0052278000
_diffrn_orient_matrix_UB_33      0.0153707000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.897
_reflns_number_gt                6490
_reflns_number_total             9160
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 2060 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(6)
_refine_ls_extinction_coef       0.0041(7)
_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   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         9160
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0587
_refine_ls_restrained_S_all      1.030
_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)+(0.0495P)²+0.4589P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1375
_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 N(H,H)
  groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N5-H5 = N2-H2
 0.9 with sigma of 0.01
 O10-C20 \\sim O10A-C20
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(O10) \\sim Ueq, Uanis(O10A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(H20C)=Sof(H20D)=Sof(O10A)=Sof(H10C)=1-FVAR(1)
 Sof(H20A)=Sof(H20B)=Sof(O10)=Sof(H10)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C12(H12), C15(H15)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3D,H3E), C10(H10A,H10B), C11(H11A,H11B), C18(H18A,H18B),
 C20(H20A,H20B), C20(H20C,H20D)
5.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N4(H4A,H4B)
5.d Idealised Me refined as rotating group:
 N3(H3A,H3B,H3C), C8(H8A,H8B,H8C), N6(H6A,H6B,H6C), C16(H16A,H16B,H16C),
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
5.e Idealised tetrahedral OH refined as rotating group:
 O9(H9), O10(H10), O10A(H10C)
;
_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
O1 O 0.63190(18) 0.82178(11) 0.60243(13) 0.0271(4) Uani 1 1 d . . . . .
O2 O 0.59678(19) 0.55083(12) 0.77525(10) 0.0241(4) Uani 1 1 d . . . . .
O3 O 0.46557(18) 0.48527(12) 0.68631(11) 0.0251(4) Uani 1 1 d . . . . .
O4 O 0.80605(16) 0.52881(11) 0.48904(10) 0.0165(3) Uani 1 1 d . . . . .
N1 N 0.4109(2) 0.81833(14) 0.58839(14) 0.0226(5) Uani 1 1 d . . . . .
H1A H 0.407967 0.871018 0.574881 0.027 Uiso 1 1 calc R U . . .
H1B H 0.337110 0.789242 0.590754 0.027 Uiso 1 1 calc R U . . .
N2 N 0.6068(2) 0.52452(12) 0.55478(12) 0.0142(4) Uani 1 1 d D . . . .
H2 H 0.5189(13) 0.5167(16) 0.5516(17) 0.012(7) Uiso 1 1 d D . . . .
N3 N 0.6740(2) 0.52335(12) 0.33845(11) 0.0165(4) Uani 1 1 d . . . . .
H3A H 0.621663 0.513759 0.293673 0.020 Uiso 1 1 calc R U . . .
H3B H 0.756641 0.502494 0.329088 0.020 Uiso 1 1 calc R U . . .
H3C H 0.679826 0.578779 0.347502 0.020 Uiso 1 1 calc R U . . .
C1 C 0.5261(2) 0.78291(15) 0.60511(15) 0.0172(5) Uani 1 1 d . . . . .
C2 C 0.5231(2) 0.69168(15) 0.62712(15) 0.0174(5) Uani 1 1 d . . . . .
H2A H 0.468923 0.661895 0.585663 0.021 Uiso 1 1 calc R U . . .
H2B H 0.479392 0.684954 0.681460 0.021 Uiso 1 1 calc R U . . .
C3 C 0.6603(2) 0.65269(14) 0.63068(14) 0.0151(4) Uani 1 1 d . . . . .
H3D H 0.707155 0.673064 0.680405 0.018 Uiso 1 1 calc R U . . .
H3E H 0.711804 0.670347 0.581707 0.018 Uiso 1 1 calc R U . . .
C4 C 0.6554(2) 0.55744(14) 0.63321(13) 0.0133(4) Uani 1 1 d . . . . .
H4 H 0.747243 0.536049 0.642916 0.016 Uiso 1 1 calc R U . . .
C5 C 0.5657(2) 0.52788(15) 0.70358(14) 0.0169(5) Uani 1 1 d . . . . .
C6 C 0.6851(2) 0.51522(14) 0.48894(13) 0.0125(4) Uani 1 1 d . . . . .
C7 C 0.6153(2) 0.48260(14) 0.41203(13) 0.0153(4) Uani 1 1 d . . . . .
H7 H 0.518526 0.496275 0.415172 0.018 Uiso 1 1 calc R U . . .
C8 C 0.6320(3) 0.38919(16) 0.40480(16) 0.0267(6) Uani 1 1 d . . . . .
H8A H 0.591965 0.370029 0.353086 0.040 Uiso 1 1 calc R U . . .
H8B H 0.588088 0.362121 0.451544 0.040 Uiso 1 1 calc R U . . .
H8C H 0.726824 0.375365 0.405140 0.040 Uiso 1 1 calc R U . . .
O5 O 0.12974(17) 0.81716(11) 0.58005(12) 0.0225(4) Uani 1 1 d . . . . .
O6 O 0.11674(19) 0.54812(13) 0.78276(10) 0.0263(4) Uani 1 1 d . . . . .
O7 O -0.03848(18) 0.50282(12) 0.69602(11) 0.0239(4) Uani 1 1 d . . . . .
O8 O 0.30549(16) 0.52491(11) 0.49341(10) 0.0187(4) Uani 1 1 d . . . . .
O9 O 0.7533(2) 0.33114(18) 0.73509(14) 0.0494(7) Uani 1 1 d . . . . .
H9 H 0.680845 0.328372 0.709510 0.074 Uiso 1 1 calc R U . . .
N4 N -0.0915(2) 0.81939(14) 0.59409(14) 0.0248(5) Uani 1 1 d . . . . .
H4A H -0.095764 0.871472 0.578555 0.030 Uiso 1 1 calc R U . . .
H4B H -0.164562 0.792520 0.607108 0.030 Uiso 1 1 calc R U . . .
N5 N 0.1098(2) 0.52057(13) 0.56328(12) 0.0151(4) Uani 1 1 d D . . . .
H5 H 0.0233(14) 0.5099(19) 0.561(2) 0.032(9) Uiso 1 1 d D . . . .
N6 N 0.1548(2) 0.51178(14) 0.34845(12) 0.0224(5) Uani 1 1 d . . . . .
H6A H 0.097226 0.499267 0.306957 0.027 Uiso 1 1 calc R U . . .
H6B H 0.238470 0.496684 0.333521 0.027 Uiso 1 1 calc R U . . .
H6C H 0.152561 0.567168 0.358338 0.027 Uiso 1 1 calc R U . . .
C9 C 0.0255(2) 0.78126(15) 0.59789(15) 0.0165(5) Uani 1 1 d . . . . .
C10 C 0.0237(2) 0.69142(14) 0.62449(15) 0.0166(5) Uani 1 1 d . . . . .
H10A H -0.030156 0.659220 0.584727 0.020 Uiso 1 1 calc R U . . .
H10B H -0.019519 0.687216 0.679223 0.020 Uiso 1 1 calc R U . . .
C11 C 0.1620(2) 0.65366(14) 0.62963(14) 0.0155(5) Uani 1 1 d . . . . .
H11A H 0.209336 0.677883 0.677430 0.019 Uiso 1 1 calc R U . . .
H11B H 0.212134 0.668437 0.579161 0.019 Uiso 1 1 calc R U . . .
C12 C 0.1604(2) 0.55878(14) 0.63870(13) 0.0141(4) Uani 1 1 d . . . . .
H12 H 0.253092 0.538948 0.648684 0.017 Uiso 1 1 calc R U . . .
C13 C 0.0731(2) 0.53341(15) 0.71174(14) 0.0160(5) Uani 1 1 d . . . . .
C14 C 0.1859(2) 0.50730(14) 0.49723(14) 0.0151(4) Uani 1 1 d . . . . .
C15 C 0.1156(2) 0.46643(16) 0.42448(15) 0.0206(5) Uani 1 1 d . . . . .
H15 H 0.017260 0.470535 0.432218 0.025 Uiso 1 1 calc R U . . .
C16 C 0.1552(3) 0.37585(17) 0.41661(19) 0.0348(7) Uani 1 1 d . . . . .
H16A H 0.114793 0.352319 0.366835 0.052 Uiso 1 1 calc R U . . .
H16B H 0.124228 0.345345 0.465218 0.052 Uiso 1 1 calc R U . . .
H16C H 0.252140 0.371606 0.412723 0.052 Uiso 1 1 calc R U . . .
C17 C 0.8443(4) 0.3268(2) 0.5964(2) 0.0469(9) Uani 1 1 d . . . . .
H17A H 0.916536 0.302013 0.564230 0.070 Uiso 1 1 calc R U . . .
H17B H 0.849584 0.387206 0.592476 0.070 Uiso 1 1 calc R U . . .
H17C H 0.758699 0.308036 0.574437 0.070 Uiso 1 1 calc R U . . .
C18 C 0.8565(3) 0.3013(2) 0.68428(19) 0.0363(7) Uani 1 1 d . . . . .
H18A H 0.857507 0.240121 0.687115 0.044 Uiso 1 1 calc R U . . .
H18B H 0.942453 0.321462 0.706100 0.044 Uiso 1 1 calc R U . . .
C19 C 0.2565(4) 0.3171(2) 0.6642(3) 0.0689(13) Uani 1 1 d . . . . .
H19A H 0.236358 0.314091 0.723350 0.103 Uiso 1 1 calc R U . . .
H19B H 0.188582 0.286743 0.633155 0.103 Uiso 1 1 calc R U . . .
H19C H 0.257089 0.375039 0.646576 0.103 Uiso 1 1 calc R U . . .
C20 C 0.3844(4) 0.2809(2) 0.6490(3) 0.0620(12) Uani 1 1 d D . . . .
H20A H 0.402874 0.244477 0.696715 0.074 Uiso 0.329(19) 1 calc R U P A 1
H20B H 0.372949 0.244093 0.600672 0.074 Uiso 0.329(19) 1 calc R U P A 1
H20C H 0.380104 0.221515 0.663490 0.074 Uiso 0.671(19) 1 calc R U P A 2
H20D H 0.403162 0.284646 0.589095 0.074 Uiso 0.671(19) 1 calc R U P A 2
O10 O 0.5014(9) 0.3255(7) 0.6347(15) 0.057(5) Uani 0.329(19) 1 d D U P A 1
H10 H 0.482358 0.374385 0.621853 0.086 Uiso 0.329(19) 1 calc R U P A 1
O10A O 0.4893(6) 0.3162(3) 0.6914(7) 0.053(2) Uani 0.671(19) 1 d D U P A 2
H10C H 0.488357 0.367666 0.684382 0.080 Uiso 0.671(19) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.237(3) . ?
O2 C5 1.258(3) . ?
O3 C5 1.253(3) . ?
O4 C6 1.237(3) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C1 1.321(3) . ?
N2 H2 0.895(12) . ?
N2 C4 1.462(3) . ?
N2 C6 1.335(3) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
N3 C7 1.485(3) . ?
C1 C2 1.518(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.519(3) . ?
C3 H3D 0.9900 . ?
C3 H3E 0.9900 . ?
C3 C4 1.541(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.530(3) . ?
C6 C7 1.524(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.524(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O5 C9 1.233(3) . ?
O6 C13 1.254(3) . ?
O7 C13 1.254(3) . ?
O8 C14 1.239(3) . ?
O9 H9 0.8400 . ?
O9 C18 1.411(4) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N4 C9 1.331(3) . ?
N5 H5 0.889(13) . ?
N5 C12 1.460(3) . ?
N5 C14 1.333(3) . ?
N6 H6A 0.9100 . ?
N6 H6B 0.9100 . ?
N6 H6C 0.9100 . ?
N6 C15 1.486(3) . ?
C9 C10 1.515(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.522(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.541(3) . ?
C12 H12 1.0000 . ?
C12 C13 1.529(3) . ?
C14 C15 1.525(3) . ?
C15 H15 1.0000 . ?
C15 C16 1.523(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 C18 1.488(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 C20 1.435(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 H20C 0.9900 . ?
C20 H20D 0.9900 . ?
C20 O10 1.400(8) . ?
C20 O10A 1.383(5) . ?
O10 H10 0.8400 . ?
O10A H10C 0.8400 . ?

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 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
C4 N2 H2 115.6(18) . . ?
C6 N2 H2 121.5(18) . . ?
C6 N2 C4 122.54(19) . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C7 N3 H3A 109.5 . . ?
C7 N3 H3B 109.5 . . ?
C7 N3 H3C 109.5 . . ?
O1 C1 N1 121.9(2) . . ?
O1 C1 C2 121.3(2) . . ?
N1 C1 C2 116.9(2) . . ?
C1 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C1 C2 C3 113.2(2) . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C2 C3 H3D 109.0 . . ?
C2 C3 H3E 109.0 . . ?
C2 C3 C4 112.75(19) . . ?
H3D C3 H3E 107.8 . . ?
C4 C3 H3D 109.0 . . ?
C4 C3 H3E 109.0 . . ?
N2 C4 C3 110.59(18) . . ?
N2 C4 H4 108.7 . . ?
N2 C4 C5 109.65(19) . . ?
C3 C4 H4 108.7 . . ?
C5 C4 C3 110.53(19) . . ?
C5 C4 H4 108.7 . . ?
O2 C5 C4 116.6(2) . . ?
O3 C5 O2 124.6(2) . . ?
O3 C5 C4 118.7(2) . . ?
O4 C6 N2 124.1(2) . . ?
O4 C6 C7 121.1(2) . . ?
N2 C6 C7 114.8(2) . . ?
N3 C7 C6 108.59(18) . . ?
N3 C7 H7 109.3 . . ?
N3 C7 C8 109.52(19) . . ?
C6 C7 H7 109.3 . . ?
C8 C7 C6 110.8(2) . . ?
C8 C7 H7 109.3 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C18 O9 H9 109.5 . . ?
H4A N4 H4B 120.0 . . ?
C9 N4 H4A 120.0 . . ?
C9 N4 H4B 120.0 . . ?
C12 N5 H5 117(2) . . ?
C14 N5 H5 120(2) . . ?
C14 N5 C12 122.6(2) . . ?
H6A N6 H6B 109.5 . . ?
H6A N6 H6C 109.5 . . ?
H6B N6 H6C 109.5 . . ?
C15 N6 H6A 109.5 . . ?
C15 N6 H6B 109.5 . . ?
C15 N6 H6C 109.5 . . ?
O5 C9 N4 121.6(2) . . ?
O5 C9 C10 121.9(2) . . ?
N4 C9 C10 116.5(2) . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C9 C10 C11 112.9(2) . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C10 C11 C12 113.26(19) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
N5 C12 C11 110.18(18) . . ?
N5 C12 H12 109.0 . . ?
N5 C12 C13 109.49(19) . . ?
C11 C12 H12 108.9 . . ?
C13 C12 C11 110.29(19) . . ?
C13 C12 H12 108.9 . . ?
O6 C13 C12 117.2(2) . . ?
O7 C13 O6 125.1(2) . . ?
O7 C13 C12 117.6(2) . . ?
O8 C14 N5 124.1(2) . . ?
O8 C14 C15 120.8(2) . . ?
N5 C14 C15 115.1(2) . . ?
N6 C15 C14 107.65(19) . . ?
N6 C15 H15 109.5 . . ?
N6 C15 C16 109.6(2) . . ?
C14 C15 H15 109.5 . . ?
C16 C15 C14 111.1(2) . . ?
C16 C15 H15 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
O9 C18 C17 113.7(3) . . ?
O9 C18 H18A 108.8 . . ?
O9 C18 H18B 108.8 . . ?
C17 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
C19 C20 H20A 106.1 . . ?
C19 C20 H20B 106.1 . . ?
C19 C20 H20C 108.4 . . ?
C19 C20 H20D 108.4 . . ?
H20A C20 H20B 106.3 . . ?
H20C C20 H20D 107.4 . . ?
O10 C20 C19 125.0(5) . . ?
O10 C20 H20A 106.1 . . ?
O10 C20 H20B 106.1 . . ?
O10A C20 C19 115.6(5) . . ?
O10A C20 H20C 108.4 . . ?
O10A C20 H20D 108.4 . . ?
C20 O10 H10 109.5 . . ?
C20 O10A H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -9.5(3) . . . . ?
O4 C6 C7 N3 -38.6(3) . . . . ?
O4 C6 C7 C8 81.7(3) . . . . ?
N1 C1 C2 C3 170.0(2) . . . . ?
N2 C4 C5 O2 179.2(2) . . . . ?
N2 C4 C5 O3 -3.0(3) . . . . ?
N2 C6 C7 N3 143.6(2) . . . . ?
N2 C6 C7 C8 -96.1(3) . . . . ?
C1 C2 C3 C4 -166.88(19) . . . . ?
C2 C3 C4 N2 68.1(2) . . . . ?
C2 C3 C4 C5 -53.5(3) . . . . ?
C3 C4 C5 O2 -58.6(3) . . . . ?
C3 C4 C5 O3 119.2(2) . . . . ?
C4 N2 C6 O4 4.2(4) . . . . ?
C4 N2 C6 C7 -178.1(2) . . . . ?
C6 N2 C4 C3 81.5(3) . . . . ?
C6 N2 C4 C5 -156.4(2) . . . . ?
O5 C9 C10 C11 2.3(3) . . . . ?
O8 C14 C15 N6 -46.1(3) . . . . ?
O8 C14 C15 C16 73.9(3) . . . . ?
N4 C9 C10 C11 -178.2(2) . . . . ?
N5 C12 C13 O6 167.0(2) . . . . ?
N5 C12 C13 O7 -15.9(3) . . . . ?
N5 C14 C15 N6 134.9(2) . . . . ?
N5 C14 C15 C16 -105.1(3) . . . . ?
C9 C10 C11 C12 -168.0(2) . . . . ?
C10 C11 C12 N5 67.4(2) . . . . ?
C10 C11 C12 C13 -53.5(3) . . . . ?
C11 C12 C13 O6 -71.6(3) . . . . ?
C11 C12 C13 O7 105.5(2) . . . . ?
C12 N5 C14 O8 0.8(4) . . . . ?
C12 N5 C14 C15 179.8(2) . . . . ?
C14 N5 C12 C11 82.1(3) . . . . ?
C14 N5 C12 C13 -156.4(2) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.623
_oxdiff_exptl_absorpt_empirical_full_min 0.763
####################################################################### 
# 
# 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_r20220617c
_database_code_depnum_ccdc_archive 'CCDC 2292121'
loop_
_audit_author_name
_audit_author_address
'Jinqiu Fu'
;Zhengzhou University
China
;
_audit_update_record             
;
2023-11-10 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;
_audit_creation_date             2022-06-18
_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         'C8 H15 N3 O4, 2(H2 O)'
_chemical_formula_sum            'C8 H19 N3 O6'
_chemical_formula_weight         253.26
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.0124(3)
_cell_length_b                   15.2769(10)
_cell_length_c                   16.3628(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1252.96(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5733
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      31.6230
_cell_measurement_theta_min      2.5210
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15740
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.907
_diffrn_reflns_theta_min         2.824
_diffrn_ambient_temperature      294.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    8.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  35.00   1.00    8.00    --  -25.00  45.00  90.00  150
  3  ω   -115.00   5.00   1.00    8.00    --  -25.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn70'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0020855000
_diffrn_orient_matrix_UB_12      -0.0461754000
_diffrn_orient_matrix_UB_13      -0.0045839000
_diffrn_orient_matrix_UB_21      0.0098273000
_diffrn_orient_matrix_UB_22      -0.0049618000
_diffrn_orient_matrix_UB_23      0.0429842000
_diffrn_orient_matrix_UB_31      -0.1411510000
_diffrn_orient_matrix_UB_32      0.0003247000
_diffrn_orient_matrix_UB_33      0.0030675000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.671
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.861
_reflns_number_gt                2861
_reflns_number_total             4257
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 765 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.1(10)
_refine_ls_extinction_coef       0.032(4)
_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   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         4257
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0559
_refine_ls_restrained_S_all      1.034
_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)+(0.0503P)²+0.0169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1313
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 N2-H2
 0.9 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(O6) \\sim Ueq, Uanis(O7) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(O7)=Sof(H7C)=Sof(H7D)=1-FVAR(1)
 Sof(O6)=Sof(H6C)=Sof(H6D)=FVAR(1)
5.a Free rotating group:
 O5(H5A,H5B), O6(H6C,H6D), O7(H7C,H7D)
5.b Ternary CH refined with riding coordinates:
 C2(H2A), C4(H4)
5.c Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
5.d X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
5.e Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C1(H1D,H1E,H1F)
;
_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
O1 O 0.1329(3) 0.48754(12) 0.52568(10) 0.0339(4) Uani 1 1 d . . . . .
O2 O 0.8165(4) 0.49174(13) 0.72926(11) 0.0430(5) Uani 1 1 d . . . . .
O3 O 0.5251(4) 0.42079(12) 0.80640(9) 0.0401(5) Uani 1 1 d . . . . .
O4 O 0.9221(4) 0.16884(11) 0.58781(14) 0.0485(5) Uani 1 1 d . . . . .
N1 N 0.4369(5) 0.51447(14) 0.38388(11) 0.0350(5) Uani 1 1 d . . . . .
H1A H 0.559707 0.526769 0.346324 0.042 Uiso 1 1 calc R U . . .
H1B H 0.279547 0.535273 0.367792 0.042 Uiso 1 1 calc R U . . .
H1C H 0.425785 0.456726 0.390252 0.042 Uiso 1 1 calc R U . . .
N2 N 0.5254(4) 0.48449(13) 0.59442(11) 0.0281(4) Uani 1 1 d D . . . .
H2 H 0.697(3) 0.4984(18) 0.5949(19) 0.043(8) Uiso 1 1 d D . . . .
N3 N 0.4797(5) 0.16217(14) 0.58149(16) 0.0480(7) Uani 1 1 d . . . . .
H3A H 0.486530 0.109805 0.562319 0.058 Uiso 1 1 calc R U . . .
H3B H 0.327848 0.187022 0.589281 0.058 Uiso 1 1 calc R U . . .
C1 C 0.4312(8) 0.65192(18) 0.46327(18) 0.0569(9) Uani 1 1 d . . . . .
H1D H 0.241121 0.656216 0.457440 0.085 Uiso 1 1 calc R U . . .
H1E H 0.516370 0.681540 0.418571 0.085 Uiso 1 1 calc R U . . .
H1F H 0.484623 0.678526 0.513842 0.085 Uiso 1 1 calc R U . . .
C2 C 0.5133(5) 0.55580(16) 0.46318(14) 0.0331(5) Uani 1 1 d . . . . .
H2A H 0.706819 0.551403 0.470603 0.040 Uiso 1 1 calc R U . . .
C3 C 0.3731(5) 0.50573(14) 0.53101(13) 0.0263(5) Uani 1 1 d . . . . .
C4 C 0.4258(5) 0.43468(14) 0.66431(12) 0.0260(5) Uani 1 1 d . . . . .
H4 H 0.244903 0.454964 0.676817 0.031 Uiso 1 1 calc R U . . .
C5 C 0.6026(5) 0.45166(15) 0.73900(13) 0.0284(5) Uani 1 1 d . . . . .
C6 C 0.4130(5) 0.33626(15) 0.64398(14) 0.0280(5) Uani 1 1 d . . . . .
H6A H 0.324707 0.305672 0.688340 0.034 Uiso 1 1 calc R U . . .
H6B H 0.307003 0.328041 0.594973 0.034 Uiso 1 1 calc R U . . .
C7 C 0.6887(5) 0.29648(16) 0.63077(15) 0.0321(5) Uani 1 1 d . . . . .
H7A H 0.785178 0.333774 0.592972 0.038 Uiso 1 1 calc R U . . .
H7B H 0.783271 0.298249 0.682461 0.038 Uiso 1 1 calc R U . . .
C8 C 0.7014(5) 0.20425(16) 0.59888(16) 0.0331(5) Uani 1 1 d . . . . .
O5 O 0.5711(6) 0.23490(16) 0.83398(18) 0.0698(7) Uani 1 1 d G . . . .
H5A H 0.418810 0.213192 0.823484 0.105 Uiso 1 1 d G U . . .
H5B H 0.555028 0.288981 0.822787 0.105 Uiso 1 1 d G U . . .
O6 O 0.9206(13) 0.6560(6) 0.6561(11) 0.077(4) Uani 0.60(3) 1 d G U P A 1
H6C H 1.087110 0.663059 0.663432 0.115 Uiso 0.60(3) 1 d G U P A 1
H6D H 0.886864 0.606476 0.677399 0.115 Uiso 0.60(3) 1 d G U P A 1
O7 O 0.930(2) 0.6732(7) 0.7073(17) 0.084(5) Uani 0.40(3) 1 d G U P A 2
H7C H 0.955879 0.618508 0.712053 0.126 Uiso 0.40(3) 1 d G U P A 2
H7D H 1.049619 0.690189 0.674070 0.126 Uiso 0.40(3) 1 d G U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.239(3) . ?
O2 C5 1.245(3) . ?
O3 C5 1.261(3) . ?
O4 C8 1.245(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C2 1.493(3) . ?
N2 H2 0.888(12) . ?
N2 C3 1.329(3) . ?
N2 C4 1.462(3) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N3 C8 1.315(3) . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C1 H1F 0.9600 . ?
C1 C2 1.525(4) . ?
C2 H2A 0.9800 . ?
C2 C3 1.520(3) . ?
C4 H4 0.9800 . ?
C4 C5 1.532(3) . ?
C4 C6 1.541(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.525(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.504(3) . ?
O5 H5A 0.8499 . ?
O5 H5B 0.8501 . ?
O6 H6C 0.8499 . ?
O6 H6D 0.8499 . ?
O7 H7C 0.8500 . ?
O7 H7D 0.8500 . ?

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 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
C3 N2 H2 120(2) . . ?
C3 N2 C4 122.8(2) . . ?
C4 N2 H2 117(2) . . ?
H3A N3 H3B 120.0 . . ?
C8 N3 H3A 120.0 . . ?
C8 N3 H3B 120.0 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
N1 C2 C1 109.8(2) . . ?
N1 C2 H2A 109.4 . . ?
N1 C2 C3 107.65(19) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 C1 111.1(2) . . ?
C3 C2 H2A 109.4 . . ?
O1 C3 N2 124.0(2) . . ?
O1 C3 C2 120.7(2) . . ?
N2 C3 C2 115.3(2) . . ?
N2 C4 H4 108.4 . . ?
N2 C4 C5 109.79(19) . . ?
N2 C4 C6 110.70(18) . . ?
C5 C4 H4 108.4 . . ?
C5 C4 C6 111.20(18) . . ?
C6 C4 H4 108.4 . . ?
O2 C5 O3 124.1(2) . . ?
O2 C5 C4 118.6(2) . . ?
O3 C5 C4 117.2(2) . . ?
C4 C6 H6A 109.1 . . ?
C4 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 C4 112.42(19) . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C6 C7 H7A 107.9 . . ?
C6 C7 H7B 107.9 . . ?
H7A C7 H7B 107.2 . . ?
C8 C7 C6 117.4(2) . . ?
C8 C7 H7A 107.9 . . ?
C8 C7 H7B 107.9 . . ?
O4 C8 N3 120.5(2) . . ?
O4 C8 C7 119.7(2) . . ?
N3 C8 C7 119.8(2) . . ?
H5A O5 H5B 104.5 . . ?
H6C O6 H6D 104.5 . . ?
H7C O7 H7D 104.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 O1 -46.8(3) . . . . ?
N1 C2 C3 N2 133.5(2) . . . . ?
N2 C4 C5 O2 -10.2(3) . . . . ?
N2 C4 C5 O3 172.4(2) . . . . ?
N2 C4 C6 C7 66.3(2) . . . . ?
C1 C2 C3 O1 73.4(3) . . . . ?
C1 C2 C3 N2 -106.2(3) . . . . ?
C3 N2 C4 C5 -157.5(2) . . . . ?
C3 N2 C4 C6 79.3(3) . . . . ?
C4 N2 C3 O1 1.8(4) . . . . ?
C4 N2 C3 C2 -178.60(19) . . . . ?
C4 C6 C7 C8 -171.5(2) . . . . ?
C5 C4 C6 C7 -56.0(2) . . . . ?
C6 C4 C5 O2 112.6(2) . . . . ?
C6 C4 C5 O3 -64.7(3) . . . . ?
C6 C7 C8 O4 -179.4(2) . . . . ?
C6 C7 C8 N3 1.8(4) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.519
_oxdiff_exptl_absorpt_empirical_full_min 0.592
