# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

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

data_r20210618c
_database_code_depnum_ccdc_archive 'CCDC 2221414'
loop_
_audit_author_name
_audit_author_address
'Hu Xingchen'
;School of Chemical Engineering and Technology, Tianjin University
China
;
_audit_update_record             
;
2023-04-03 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;
_audit_creation_date             2023-03-28
_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         'C9 H9 O5, 0.163(H2 O), C14 H19 N4 O3'
_chemical_formula_sum            'C23 H28.33 N4 O8.16'
_chemical_formula_weight         491.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.1553(5)
_cell_length_b                   8.8076(3)
_cell_length_c                   22.3040(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.608(3)
_cell_angle_gamma                90
_cell_volume                     2380.13(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      33.6070
_cell_measurement_theta_min      1.8630
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93023
_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            ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1038
_exptl_crystal_size_max          0.23
_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  0.0412
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            18662
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.832
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   1.00    1.00    --  -30.00  45.00   0.00  180
  2  ω   -120.00  30.00   1.00    1.00    --  -30.00  45.00  90.00  150
  3  ω   -120.00   0.00   1.00    1.00    --  -30.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4023
_reflns_number_total             4860
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0103(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     458
_refine_ls_number_reflns         4860
_refine_ls_number_restraints     600
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.019
_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)+(0.0488P)²+0.9516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1115
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O5-H5
 0.84 with sigma of 0.01
 N1-H1A = N1-H1B = N2-H2A = N2-H2B = N4-H4
 0.88 with sigma of 0.01
 H1A-H1B = H2A-H2B
 1.5 with sigma of 0.01
 O7-C17 \\sim O8A-C19A
 with sigma of 0.02
 O7-C21 \\sim O8A-C22A
 with sigma of 0.02
 O8-C19 \\sim O7A-C17A
 with sigma of 0.02
 O8-C22 \\sim O7A-C21A
 with sigma of 0.02
 O9-C18 \\sim O9A-C18A
 with sigma of 0.02
 C16-C17 \\sim C20A-C19A
 with sigma of 0.02
 C20-C19 \\sim C16A-C17A
 with sigma of 0.02
 C19-C18 \\sim C17A-C18A
 with sigma of 0.02
 C18-C17 \\sim C18A-C19A
 with sigma of 0.02
 O7-C16 \\sim O8A-C20A
 with sigma of 0.04
 O7-C18 \\sim O8A-C18A
 with sigma of 0.04
 O8-C20 \\sim O7A-C16A
 with sigma of 0.04
 O8-C18 \\sim O7A-C18A
 with sigma of 0.04
 O9-C19 \\sim O9A-C17A
 with sigma of 0.04
 O9-C17 \\sim O9A-C19A
 with sigma of 0.04
 C16-C20 \\sim C20A-C16A
 with sigma of 0.04
 C16-C18 \\sim C20A-C18A
 with sigma of 0.04
 C20-C18 \\sim C16A-C18A
 with sigma of 0.04
 C19-C22 \\sim C17A-C21A
 with sigma of 0.04
 C19-C17 \\sim C17A-C19A
 with sigma of 0.04
 C17-C21 \\sim C19A-C22A
 with sigma of 0.04
 C15-C16 \\sim C15A-C20A
 with sigma of 0.02
 C15-C20 \\sim C15A-C16A
 with sigma of 0.02
 C15-C19 \\sim C15A-C17A
 with sigma of 0.04
 C15-C17 \\sim C15A-C19A
 with sigma of 0.04
 C14-C16 \\sim C14-C20A
 with sigma of 0.04
 C14-C20 \\sim C14-C16A
 with sigma of 0.04
 C14-C15 \\sim C14-C15A
 with sigma of 0.02
 C15-C14 \\sim C14A-C15A
 with sigma of 0.01
 O9-C23 \\sim O9A-C23A
 with sigma of 0.02
 C18-C23 \\sim C18A-C23A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
O7 \\sim O8 \\sim O9 \\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim C18 \\sim
C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim O7A \\sim O8A \\sim O9A \\sim
C14A \\sim C20A \\sim C15A \\sim C16A \\sim C17A \\sim C18A \\sim C19A \\sim
C21A \\sim C22A \\sim C23A: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01 within 2A
Uanis(O7) \\sim Ueq, Uanis(O8) \\sim Ueq, Uanis(O9) \\sim Ueq, Uanis(C14) \\sim
Ueq, Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq,
Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C21)
\\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(O7A) \\sim Ueq,
Uanis(O8A) \\sim Ueq, Uanis(O9A) \\sim Ueq, Uanis(C14A) \\sim Ueq, Uanis(C20A)
\\sim Ueq, Uanis(C15A) \\sim Ueq, Uanis(C16A) \\sim Ueq, Uanis(C17A) \\sim Ueq,
Uanis(C18A) \\sim Ueq, Uanis(C19A) \\sim Ueq, Uanis(C21A) \\sim Ueq,
Uanis(C22A) \\sim Ueq, Uanis(C23A) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4. Others
 Sof(O7A)=Sof(O8A)=Sof(O9A)=Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(C20A)=Sof(H20A)=
 Sof(C15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(C18A)=Sof(C19A)=Sof(C21A)=
 Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C22A)=Sof(H22D)=Sof(H22E)=Sof(H22F)=
 Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=1-FVAR(1)
 Sof(O7)=Sof(O8)=Sof(O9)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(C16)=
 Sof(H16)=Sof(C17)=Sof(C18)=Sof(C19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21A)=
 Sof(H21B)=Sof(H21C)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=Sof(C23)=Sof(H23A)=
 Sof(H23B)=Sof(H23C)=FVAR(1)
 Sof(O6)=Sof(H6A)=Sof(H6B)=FVAR(2)
5.a Riding coordinates:
 O6(H6A,H6B)
5.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C14A(H14C,H14D)
5.c Me refined with riding coordinates:
 C9(H9A,H9B,H9C)
5.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C12(H12), C16(H16), C20(H20), C20A(H20A), C16A(H16A)
5.e Fitted hexagon refined as free rotating group:
 C20A(C15A,C16A,C17A,C18A,C19A)
5.f Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C21A(H21D,H21E,H21F), C22A(H22D,H22E,H22F), C23A(H23D,H23E,H23F)
;
_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 0.05074(8) 0.01116(12) 0.32219(4) 0.0267(3) Uani 1 1 d . . . . .
O2 O 0.09483(9) 0.06616(13) 0.41822(4) 0.0287(3) Uani 1 1 d . . . . .
O3 O 0.38428(10) 0.21587(14) 0.21959(5) 0.0403(3) Uani 1 1 d . . . . .
O4 O 0.40102(10) 0.46466(14) 0.40372(5) 0.0353(3) Uani 1 1 d . . . . .
O5 O 0.46750(8) 0.42952(12) 0.29393(4) 0.0251(3) Uani 1 1 d D . . . .
H5 H 0.4576(16) 0.447(2) 0.2564(5) 0.038 Uiso 1 1 d D U . . .
C1 C 0.11216(11) 0.07379(16) 0.36388(6) 0.0206(3) Uani 1 1 d . . . . .
C2 C 0.20956(11) 0.16395(16) 0.34571(6) 0.0209(3) Uani 1 1 d . . . . .
C3 C 0.24580(12) 0.14606(17) 0.28859(7) 0.0238(3) Uani 1 1 d . . . . .
H3 H 0.209518 0.077182 0.260808 0.029 Uiso 1 1 calc R U . . .
C4 C 0.33551(12) 0.22985(17) 0.27260(7) 0.0249(3) Uani 1 1 d . . . . .
C5 C 0.38452(11) 0.33841(16) 0.31128(6) 0.0210(3) Uani 1 1 d . . . . .
C6 C 0.34863(12) 0.35399(18) 0.36893(6) 0.0242(3) Uani 1 1 d . . . . .
C7 C 0.26242(12) 0.26469(18) 0.38635(6) 0.0242(3) Uani 1 1 d . . . . .
H7 H 0.239708 0.272593 0.425999 0.029 Uiso 1 1 calc R U . . .
C8 C 0.33589(16) 0.1132(2) 0.17605(8) 0.0444(5) Uani 1 1 d . . . . .
H8A H 0.338420 0.010088 0.192644 0.067 Uiso 1 1 calc R U . . .
H8B H 0.376898 0.116296 0.139994 0.067 Uiso 1 1 calc R U . . .
H8C H 0.258955 0.142234 0.165464 0.067 Uiso 1 1 calc R U . . .
C9 C 0.3586(2) 0.4926(4) 0.46058(9) 0.0928(12) Uani 1 1 d . . . . .
H9A H 0.401708 0.573242 0.481655 0.139 Uiso 1 1 calc R U . . .
H9B H 0.281195 0.524123 0.454327 0.139 Uiso 1 1 calc R U . . .
H9C H 0.363748 0.399631 0.484782 0.139 Uiso 1 1 calc R U . . .
O6 O 0.4559(6) 0.2338(8) 0.5121(3) 0.034(2) Uani 0.163(4) 1 d . . P . .
H6A H 0.519918 0.212410 0.501861 0.052 Uiso 0.163(4) 1 d R U P . .
H6B H 0.433178 0.184600 0.541481 0.052 Uiso 0.163(4) 1 d R U P . .
N1 N 0.87114(11) 0.07695(16) 0.11871(6) 0.0287(3) Uani 1 1 d D . . . .
H1A H 0.8948(14) 0.081(2) 0.0829(4) 0.034 Uiso 1 1 d D U . . .
H1B H 0.9099(13) 0.0282(18) 0.1475(5) 0.034 Uiso 1 1 d D U . . .
N2 N 0.58847(11) 0.38676(16) 0.04454(6) 0.0283(3) Uani 1 1 d D . . . .
H2A H 0.6134(13) 0.3865(19) 0.0089(5) 0.034 Uiso 1 1 d D U . . .
H2B H 0.5313(11) 0.4422(17) 0.0516(7) 0.034 Uiso 1 1 d D U . . .
N3 N 0.72998(10) 0.22747(14) 0.08010(5) 0.0227(3) Uani 1 1 d . . . . .
N4 N 0.59600(10) 0.31250(13) 0.14301(5) 0.0192(3) Uani 1 1 d D . . . .
H4 H 0.5431(11) 0.3769(16) 0.1500(7) 0.023 Uiso 1 1 d D U . . .
C10 C 0.77951(12) 0.15321(16) 0.12758(6) 0.0202(3) Uani 1 1 d . . . . .
C11 C 0.63990(12) 0.30831(16) 0.08915(6) 0.0202(3) Uani 1 1 d . . . . .
C12 C 0.64507(11) 0.23612(15) 0.19063(6) 0.0185(3) Uani 1 1 d . . . . .
H12 H 0.613258 0.240084 0.228132 0.022 Uiso 1 1 calc R U . . .
C13 C 0.73795(11) 0.15459(15) 0.18613(6) 0.0183(3) Uani 1 1 d . . . . .
O7 O 0.5027(2) -0.0272(4) 0.37414(14) 0.0412(6) Uani 0.8451(14) 1 d D U P A 1
O8 O 0.78922(13) 0.29676(17) 0.44151(6) 0.0387(4) Uani 0.8451(14) 1 d D U P A 1
O9 O 0.59837(12) 0.15659(18) 0.45743(6) 0.0403(4) Uani 0.8451(14) 1 d D U P A 1
C14 C 0.7987(7) 0.0750(7) 0.23802(19) 0.0235(8) Uani 0.8451(14) 1 d D U P A 1
H14A H 0.874975 0.115040 0.243229 0.028 Uiso 0.8451(14) 1 calc R U P A 1
H14B H 0.803290 -0.034506 0.228488 0.028 Uiso 0.8451(14) 1 calc R U P A 1
C15 C 0.74508(17) 0.0931(3) 0.29701(9) 0.0242(4) Uani 0.8451(14) 1 d D U P A 1
C16 C 0.64711(17) 0.0191(2) 0.30634(8) 0.0268(4) Uani 0.8451(14) 1 d D U P A 1
H16 H 0.613573 -0.045920 0.276182 0.032 Uiso 0.8451(14) 1 calc R U P A 1
C17 C 0.59813(17) 0.0405(2) 0.36004(8) 0.0296(4) Uani 0.8451(14) 1 d D U P A 1
C18 C 0.64774(17) 0.1356(2) 0.40446(9) 0.0301(4) Uani 0.8451(14) 1 d D U P A 1
C19 C 0.74617(17) 0.2086(2) 0.39507(8) 0.0297(4) Uani 0.8451(14) 1 d D U P A 1
C20 C 0.79489(17) 0.1876(2) 0.34107(9) 0.0269(4) Uani 0.8451(14) 1 d D U P A 1
H20 H 0.861987 0.237923 0.334471 0.032 Uiso 0.8451(14) 1 calc R U P A 1
C21 C 0.44839(19) -0.1253(3) 0.33016(10) 0.0431(5) Uani 0.8451(14) 1 d D U P A
1
H21A H 0.433971 -0.070019 0.292208 0.065 Uiso 0.8451(14) 1 calc R U P A 1
H21B H 0.378377 -0.160032 0.344297 0.065 Uiso 0.8451(14) 1 calc R U P A 1
H21C H 0.495552 -0.213142 0.323799 0.065 Uiso 0.8451(14) 1 calc R U P A 1
C22 C 0.8955(2) 0.3615(4) 0.43603(16) 0.0419(7) Uani 0.8451(14) 1 d D U P A 1
H22A H 0.949188 0.280262 0.431199 0.063 Uiso 0.8451(14) 1 calc R U P A 1
H22B H 0.917864 0.420239 0.472292 0.063 Uiso 0.8451(14) 1 calc R U P A 1
H22C H 0.892506 0.428421 0.400840 0.063 Uiso 0.8451(14) 1 calc R U P A 1
C23 C 0.6419(2) 0.0552(3) 0.50415(9) 0.0546(7) Uani 0.8451(14) 1 d D U P A 1
H23A H 0.597040 0.062354 0.538650 0.082 Uiso 0.8451(14) 1 calc R U P A 1
H23B H 0.718247 0.083489 0.516693 0.082 Uiso 0.8451(14) 1 calc R U P A 1
H23C H 0.639932 -0.049184 0.488901 0.082 Uiso 0.8451(14) 1 calc R U P A 1
O7A O 0.5495(6) 0.0603(10) 0.4035(3) 0.0380(11) Uani 0.1549(14) 1 d D U P A 2
O8A O 0.8602(10) 0.3582(16) 0.4299(6) 0.0369(17) Uani 0.1549(14) 1 d D U P A 2
O9A O 0.6725(6) 0.2559(9) 0.4667(3) 0.0361(11) Uani 0.1549(14) 1 d D U P A 2
C14A C 0.794(4) 0.057(4) 0.2388(10) 0.0235(17) Uani 0.1549(14) 1 d D U P A 2
H14C H 0.767820 -0.049515 0.234423 0.028 Uiso 0.1549(14) 1 calc R U P A 2
H14D H 0.874997 0.056444 0.235977 0.028 Uiso 0.1549(14) 1 calc R U P A 2
C20A C 0.8345(6) 0.2172(10) 0.3354(3) 0.0252(13) Uani 0.1549(14) 1 d DG U P A 2
H20A H 0.900616 0.255609 0.321172 0.030 Uiso 0.1549(14) 1 calc R U P A 2
C15A C 0.7691(8) 0.1165(12) 0.3004(3) 0.0250(12) Uani 0.1549(14) 1 d DG U P A 2
C16A C 0.6724(7) 0.0602(10) 0.3212(4) 0.0283(12) Uani 0.1549(14) 1 d DG U P A 2
H16A H 0.627616 -0.008592 0.297247 0.034 Uiso 0.1549(14) 1 calc R U P A 2
C17A C 0.6411(6) 0.1047(10) 0.3772(4) 0.0314(10) Uani 0.1549(14) 1 d DG U P A 2
C18A C 0.7066(7) 0.2054(10) 0.4123(3) 0.0328(11) Uani 0.1549(14) 1 d DG U P A 2
C19A C 0.8033(6) 0.2616(9) 0.3914(3) 0.0314(12) Uani 0.1549(14) 1 d DG U P A 2
C21A C 0.479(2) -0.041(3) 0.3667(14) 0.038(3) Uani 0.1549(14) 1 d D U P A 2
H21D H 0.458230 0.006979 0.327911 0.057 Uiso 0.1549(14) 1 calc R U P A 2
H21E H 0.412909 -0.064186 0.387183 0.057 Uiso 0.1549(14) 1 calc R U P A 2
H21F H 0.519350 -0.135702 0.360104 0.057 Uiso 0.1549(14) 1 calc R U P A 2
C22A C 0.9636(10) 0.4164(14) 0.4107(5) 0.041(2) Uani 0.1549(14) 1 d D U P A 2
H22D H 0.950649 0.461927 0.370621 0.061 Uiso 0.1549(14) 1 calc R U P A 2
H22E H 1.016749 0.333089 0.409158 0.061 Uiso 0.1549(14) 1 calc R U P A 2
H22F H 0.993200 0.493567 0.439251 0.061 Uiso 0.1549(14) 1 calc R U P A 2
C23A C 0.7301(11) 0.1851(16) 0.5180(4) 0.046(2) Uani 0.1549(14) 1 d D U P A 2
H23D H 0.733815 0.075260 0.511370 0.069 Uiso 0.1549(14) 1 calc R U P A 2
H23E H 0.690835 0.205251 0.553851 0.069 Uiso 0.1549(14) 1 calc R U P A 2
H23F H 0.805103 0.226377 0.523846 0.069 Uiso 0.1549(14) 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 1.2706(17) . ?
O2 C1 1.2485(17) . ?
O3 C4 1.3701(17) . ?
O3 C8 1.420(2) . ?
O4 C6 1.3706(18) . ?
O4 C9 1.428(2) . ?
O5 H5 0.851(9) . ?
O5 C5 1.3689(16) . ?
C1 C2 1.5079(19) . ?
C2 C3 1.390(2) . ?
C2 C7 1.389(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(2) . ?
C4 C5 1.390(2) . ?
C5 C6 1.397(2) . ?
C6 C7 1.390(2) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
O6 H6A 0.8497 . ?
O6 H6B 0.8503 . ?
N1 H1A 0.870(9) . ?
N1 H1B 0.877(9) . ?
N1 C10 1.3290(18) . ?
N2 H2A 0.872(9) . ?
N2 H2B 0.874(9) . ?
N2 C11 1.3260(18) . ?
N3 C10 1.3451(18) . ?
N3 C11 1.3349(18) . ?
N4 H4 0.881(9) . ?
N4 C11 1.3536(18) . ?
N4 C12 1.3545(17) . ?
C10 C13 1.4377(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.3485(19) . ?
C13 C14 1.496(7) . ?
C13 C14A 1.57(4) . ?
O7 C17 1.363(4) . ?
O7 C21 1.429(3) . ?
O8 C19 1.365(2) . ?
O8 C22 1.426(4) . ?
O9 C18 1.380(2) . ?
O9 C23 1.440(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.523(3) . ?
C15 C16 1.388(3) . ?
C15 C20 1.389(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.393(3) . ?
C17 C18 1.397(3) . ?
C18 C19 1.389(3) . ?
C19 C20 1.396(3) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O7A C17A 1.357(9) . ?
O7A C21A 1.445(17) . ?
O8A C19A 1.358(12) . ?
O8A C22A 1.454(14) . ?
O9A C18A 1.386(8) . ?
O9A C23A 1.436(11) . ?
C14A H14C 0.9900 . ?
C14A H14D 0.9900 . ?
C14A C15A 1.525(9) . ?
C20A H20A 0.9500 . ?
C20A C15A 1.3900 . ?
C20A C19A 1.3900 . ?
C15A C16A 1.3900 . ?
C16A H16A 0.9500 . ?
C16A C17A 1.3900 . ?
C17A C18A 1.3900 . ?
C18A C19A 1.3900 . ?
C21A H21D 0.9800 . ?
C21A H21E 0.9800 . ?
C21A H21F 0.9800 . ?
C22A H22D 0.9800 . ?
C22A H22E 0.9800 . ?
C22A H22F 0.9800 . ?
C23A H23D 0.9800 . ?
C23A H23E 0.9800 . ?
C23A H23F 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
C4 O3 C8 117.60(12) . . ?
C6 O4 C9 116.15(13) . . ?
C5 O5 H5 109.8(13) . . ?
O1 C1 C2 117.37(12) . . ?
O2 C1 O1 123.51(13) . . ?
O2 C1 C2 119.12(12) . . ?
C3 C2 C1 120.01(12) . . ?
C7 C2 C1 119.55(12) . . ?
C7 C2 C3 120.44(13) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.27(13) . . ?
C4 C3 H3 120.4 . . ?
O3 C4 C3 125.29(13) . . ?
O3 C4 C5 113.83(12) . . ?
C3 C4 C5 120.87(13) . . ?
O5 C5 C4 121.10(13) . . ?
O5 C5 C6 119.63(13) . . ?
C4 C5 C6 119.27(13) . . ?
O4 C6 C5 115.18(12) . . ?
O4 C6 C7 124.78(13) . . ?
C7 C6 C5 119.98(13) . . ?
C2 C7 C6 119.92(13) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 C9 H9A 109.5 . . ?
O4 C9 H9B 109.5 . . ?
O4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H6A O6 H6B 117.1 . . ?
H1A N1 H1B 119.6(13) . . ?
C10 N1 H1A 117.2(11) . . ?
C10 N1 H1B 123.1(11) . . ?
H2A N2 H2B 120.3(13) . . ?
C11 N2 H2A 120.3(11) . . ?
C11 N2 H2B 119.4(11) . . ?
C11 N3 C10 117.46(12) . . ?
C11 N4 H4 121.3(11) . . ?
C11 N4 C12 120.14(12) . . ?
C12 N4 H4 117.6(10) . . ?
N1 C10 N3 117.13(12) . . ?
N1 C10 C13 119.96(12) . . ?
N3 C10 C13 122.90(12) . . ?
N2 C11 N3 120.50(13) . . ?
N2 C11 N4 117.12(12) . . ?
N3 C11 N4 122.37(12) . . ?
N4 C12 H12 119.2 . . ?
C13 C12 N4 121.65(12) . . ?
C13 C12 H12 119.2 . . ?
C10 C13 C14 120.7(2) . . ?
C10 C13 C14A 120.8(9) . . ?
C12 C13 C10 115.44(12) . . ?
C12 C13 C14 123.8(2) . . ?
C12 C13 C14A 123.6(10) . . ?
C17 O7 C21 117.4(3) . . ?
C19 O8 C22 117.2(2) . . ?
C18 O9 C23 112.13(15) . . ?
C13 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
C13 C14 C15 113.6(5) . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C16 C15 C14 120.8(3) . . ?
C16 C15 C20 120.39(17) . . ?
C20 C15 C14 118.8(3) . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.79(18) . . ?
C17 C16 H16 120.1 . . ?
O7 C17 C16 124.8(2) . . ?
O7 C17 C18 115.2(2) . . ?
C16 C17 C18 120.06(18) . . ?
O9 C18 C17 119.67(18) . . ?
O9 C18 C19 120.42(19) . . ?
C19 C18 C17 119.92(18) . . ?
O8 C19 C18 115.55(18) . . ?
O8 C19 C20 124.50(19) . . ?
C18 C19 C20 119.94(18) . . ?
C15 C20 C19 119.89(19) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
O7 C21 H21A 109.5 . . ?
O7 C21 H21B 109.5 . . ?
O7 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O8 C22 H22A 109.5 . . ?
O8 C22 H22B 109.5 . . ?
O8 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O9 C23 H23A 109.5 . . ?
O9 C23 H23B 109.5 . . ?
O9 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C17A O7A C21A 113.6(14) . . ?
C19A O8A C22A 116.3(10) . . ?
C18A O9A C23A 113.5(8) . . ?
C13 C14A H14C 109.2 . . ?
C13 C14A H14D 109.2 . . ?
H14C C14A H14D 107.9 . . ?
C15A C14A C13 112(2) . . ?
C15A C14A H14C 109.2 . . ?
C15A C14A H14D 109.2 . . ?
C15A C20A H20A 120.0 . . ?
C15A C20A C19A 120.0 . . ?
C19A C20A H20A 120.0 . . ?
C20A C15A C14A 125.5(19) . . ?
C20A C15A C16A 120.0 . . ?
C16A C15A C14A 114.5(19) . . ?
C15A C16A H16A 120.0 . . ?
C17A C16A C15A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
O7A C17A C16A 126.9(7) . . ?
O7A C17A C18A 113.1(7) . . ?
C16A C17A C18A 120.0 . . ?
O9A C18A C17A 120.0(7) . . ?
O9A C18A C19A 119.9(7) . . ?
C17A C18A C19A 120.0 . . ?
O8A C19A C20A 125.6(8) . . ?
O8A C19A C18A 114.4(8) . . ?
C18A C19A C20A 120.0 . . ?
O7A C21A H21D 109.5 . . ?
O7A C21A H21E 109.5 . . ?
O7A C21A H21F 109.5 . . ?
H21D C21A H21E 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
O8A C22A H22D 109.5 . . ?
O8A C22A H22E 109.5 . . ?
O8A C22A H22F 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
O9A C23A H23D 109.5 . . ?
O9A C23A H23E 109.5 . . ?
O9A C23A H23F 109.5 . . ?
H23D C23A H23E 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 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 -16.0(2) . . . . ?
O1 C1 C2 C7 163.88(13) . . . . ?
O2 C1 C2 C3 165.03(14) . . . . ?
O2 C1 C2 C7 -15.0(2) . . . . ?
O3 C4 C5 O5 5.3(2) . . . . ?
O3 C4 C5 C6 -174.36(14) . . . . ?
O4 C6 C7 C2 174.95(14) . . . . ?
O5 C5 C6 O4 0.8(2) . . . . ?
O5 C5 C6 C7 178.29(13) . . . . ?
C1 C2 C3 C4 180.00(13) . . . . ?
C1 C2 C7 C6 -176.68(13) . . . . ?
C2 C3 C4 O3 175.29(15) . . . . ?
C2 C3 C4 C5 -4.4(2) . . . . ?
C3 C2 C7 C6 3.2(2) . . . . ?
C3 C4 C5 O5 -174.91(14) . . . . ?
C3 C4 C5 C6 5.4(2) . . . . ?
C4 C5 C6 O4 -179.48(13) . . . . ?
C4 C5 C6 C7 -2.0(2) . . . . ?
C5 C6 C7 C2 -2.3(2) . . . . ?
C7 C2 C3 C4 0.1(2) . . . . ?
C8 O3 C4 C3 3.5(2) . . . . ?
C8 O3 C4 C5 -176.76(15) . . . . ?
C9 O4 C6 C5 174.2(2) . . . . ?
C9 O4 C6 C7 -3.2(3) . . . . ?
N1 C10 C13 C12 179.50(14) . . . . ?
N1 C10 C13 C14 2.0(4) . . . . ?
N1 C10 C13 C14A -4.9(18) . . . . ?
N3 C10 C13 C12 -0.1(2) . . . . ?
N3 C10 C13 C14 -177.6(3) . . . . ?
N3 C10 C13 C14A 175.6(18) . . . . ?
N4 C12 C13 C10 -0.8(2) . . . . ?
N4 C12 C13 C14 176.6(3) . . . . ?
N4 C12 C13 C14A -176.3(18) . . . . ?
C10 N3 C11 N2 178.58(14) . . . . ?
C10 N3 C11 N4 -2.5(2) . . . . ?
C10 C13 C14 C15 177.9(3) . . . . ?
C10 C13 C14A C15A 158.1(17) . . . . ?
C11 N3 C10 N1 -177.89(13) . . . . ?
C11 N3 C10 C13 1.7(2) . . . . ?
C11 N4 C12 C13 0.0(2) . . . . ?
C12 N4 C11 N2 -179.34(13) . . . . ?
C12 N4 C11 N3 1.7(2) . . . . ?
C12 C13 C14 C15 0.6(6) . . . . ?
C12 C13 C14A C15A -27(4) . . . . ?
C13 C14 C15 C16 71.9(5) . . . . ?
C13 C14 C15 C20 -106.9(5) . . . . ?
C13 C14A C15A C20A -94(3) . . . . ?
C13 C14A C15A C16A 87(3) . . . . ?
O7 C17 C18 O9 -1.0(3) . . . . ?
O7 C17 C18 C19 179.1(2) . . . . ?
O8 C19 C20 C15 178.87(18) . . . . ?
O9 C18 C19 O8 1.3(3) . . . . ?
O9 C18 C19 C20 -179.40(18) . . . . ?
C14 C15 C16 C17 -178.4(4) . . . . ?
C14 C15 C20 C19 178.7(4) . . . . ?
C15 C16 C17 O7 -179.5(2) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C16 C15 C20 C19 -0.1(3) . . . . ?
C16 C17 C18 O9 179.72(17) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 O8 -178.81(17) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C18 C19 C20 C15 -0.4(3) . . . . ?
C20 C15 C16 C17 0.4(3) . . . . ?
C21 O7 C17 C16 -1.0(4) . . . . ?
C21 O7 C17 C18 179.8(2) . . . . ?
C22 O8 C19 C18 174.0(2) . . . . ?
C22 O8 C19 C20 -5.3(3) . . . . ?
C23 O9 C18 C17 94.8(2) . . . . ?
C23 O9 C18 C19 -85.3(2) . . . . ?
O7A C17A C18A O9A -3.2(8) . . . . ?
O7A C17A C18A C19A -179.8(8) . . . . ?
O9A C18A C19A O8A 3.7(10) . . . . ?
O9A C18A C19A C20A -176.6(8) . . . . ?
C14A C15A C16A C17A 179(2) . . . . ?
C20A C15A C16A C17A 0.0 . . . . ?
C15A C20A C19A O8A 179.6(10) . . . . ?
C15A C20A C19A C18A 0.0 . . . . ?
C15A C16A C17A O7A 179.8(9) . . . . ?
C15A C16A C17A C18A 0.0 . . . . ?
C16A C17A C18A O9A 176.6(8) . . . . ?
C16A C17A C18A C19A 0.0 . . . . ?
C17A C18A C19A O8A -179.6(9) . . . . ?
C17A C18A C19A C20A 0.0 . . . . ?
C19A C20A C15A C14A -179(2) . . . . ?
C19A C20A C15A C16A 0.0 . . . . ?
C21A O7A C17A C16A -1.4(18) . . . . ?
C21A O7A C17A C18A 178.5(15) . . . . ?
C22A O8A C19A C20A -1.3(16) . . . . ?
C22A O8A C19A C18A 178.3(9) . . . . ?
C23A O9A C18A C17A 104.1(9) . . . . ?
C23A O9A C18A C19A -79.3(10) . . . . ?

_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
;
####################################################################### 
# 
# 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_r20211001a
_database_code_depnum_ccdc_archive 'CCDC 2221420'
loop_
_audit_author_name
_audit_author_address
XingchenHu
;Tianjin University
China
;
_audit_update_record             
;
2023-03-17 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;
_audit_creation_date             2023-03-16
_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         'C5 H3 N2 O4, C14 H19 N4 O3'
_chemical_formula_sum            'C19 H22 N6 O7'
_chemical_formula_weight         446.42
_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           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0878(6)
_cell_length_b                   7.5969(7)
_cell_length_c                   18.9464(14)
_cell_angle_alpha                91.152(7)
_cell_angle_beta                 98.566(7)
_cell_angle_gamma                103.763(8)
_cell_volume                     978.19(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5495
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      33.2280
_cell_measurement_theta_min      2.1470
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66253
_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            ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14952
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.213
_diffrn_reflns_theta_min         2.178
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.893
_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  65.00   1.00    8.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    8.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0319748000
_diffrn_orient_matrix_UB_12      -0.0788587000
_diffrn_orient_matrix_UB_13      -0.0077982000
_diffrn_orient_matrix_UB_21      -0.0008893000
_diffrn_orient_matrix_UB_22      0.0229897000
_diffrn_orient_matrix_UB_23      -0.0361274000
_diffrn_orient_matrix_UB_31      0.0993235000
_diffrn_orient_matrix_UB_32      0.0502406000
_diffrn_orient_matrix_UB_33      0.0084938000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4274
_reflns_number_total             6688
_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         0.533
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       0.018(3)
_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   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         6688
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1172
_refine_ls_R_factor_gt           0.0757
_refine_ls_restrained_S_all      1.055
_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)+(0.0876P)²+0.6681P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1892
_refine_ls_wR_factor_ref         0.2146
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C4(H4), N3(H3), C6(H6), C12(H12), C16(H16)
2.c X=CH2 refined with riding coordinates:
 N5(H5A,H5B), N6(H6A,H6B)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1617(3) 0.4841(2) 0.32332(9) 0.0265(4) Uani 1 1 d . . . . .
O2 O 0.0794(3) 0.7245(2) 0.53305(9) 0.0256(4) Uani 1 1 d . . . . .
O3 O 0.4678(3) 1.1733(2) 0.32721(10) 0.0271(4) Uani 1 1 d . . . . .
O4 O 0.4301(3) 1.2378(2) 0.43894(10) 0.0301(4) Uani 1 1 d . . . . .
N1 N 0.1273(3) 0.6081(2) 0.42817(10) 0.0192(4) Uani 1 1 d . . . . .
H1 H 0.068089 0.499239 0.439462 0.023 Uiso 1 1 calc R U . . .
N2 N 0.2402(3) 0.9122(2) 0.45815(10) 0.0196(4) Uani 1 1 d . . . . .
H2 H 0.255734 1.006555 0.488050 0.024 Uiso 1 1 calc R U . . .
C1 C 0.1926(3) 0.6200(3) 0.36260(12) 0.0191(4) Uani 1 1 d . . . . .
C2 C 0.1454(3) 0.7470(3) 0.47664(12) 0.0190(4) Uani 1 1 d . . . . .
C3 C 0.3131(3) 0.9395(3) 0.39525(12) 0.0179(4) Uani 1 1 d . . . . .
C4 C 0.2937(3) 0.8006(3) 0.34822(12) 0.0187(4) Uani 1 1 d . . . . .
H4 H 0.346797 0.820943 0.305089 0.022 Uiso 1 1 calc R U . . .
C5 C 0.4135(3) 1.1349(3) 0.38507(13) 0.0202(4) Uani 1 1 d . . . . .
O5 O 0.4522(3) 0.1630(2) 0.07727(10) 0.0268(4) Uani 1 1 d . . . . .
O6 O 0.7085(3) 0.4820(2) 0.08935(9) 0.0218(4) Uani 1 1 d . . . . .
O7 O 1.0920(2) 0.5142(2) 0.14005(9) 0.0222(4) Uani 1 1 d . . . . .
N3 N 0.6760(3) -0.4474(2) 0.32181(10) 0.0190(4) Uani 1 1 d . . . . .
H3 H 0.614207 -0.562944 0.320003 0.023 Uiso 1 1 calc R U . . .
N4 N 0.7757(3) -0.1631(2) 0.38514(10) 0.0174(4) Uani 1 1 d . . . . .
N5 N 0.6235(3) -0.4136(3) 0.43709(11) 0.0227(4) Uani 1 1 d . . . . .
H5A H 0.633424 -0.346531 0.476512 0.027 Uiso 1 1 calc R U . . .
H5B H 0.567542 -0.530551 0.435136 0.027 Uiso 1 1 calc R U . . .
N6 N 0.9342(3) 0.0851(2) 0.33587(10) 0.0194(4) Uani 1 1 d . . . . .
H6A H 0.939017 0.146771 0.376180 0.023 Uiso 1 1 calc R U . . .
H6B H 0.985757 0.140382 0.300344 0.023 Uiso 1 1 calc R U . . .
C6 C 0.7565(3) -0.3755(3) 0.26499(12) 0.0181(4) Uani 1 1 d . . . . .
H6 H 0.749201 -0.452599 0.224049 0.022 Uiso 1 1 calc R U . . .
C7 C 0.8466(3) -0.1977(3) 0.26490(12) 0.0168(4) Uani 1 1 d . . . . .
C8 C 0.8500(3) -0.0900(3) 0.32871(11) 0.0156(4) Uani 1 1 d . . . . .
C9 C 0.6917(3) -0.3396(3) 0.38148(12) 0.0168(4) Uani 1 1 d . . . . .
C10 C 0.9520(3) -0.1226(3) 0.20509(12) 0.0191(4) Uani 1 1 d . . . . .
H10A H 0.932536 -0.221354 0.167831 0.023 Uiso 1 1 calc R U . . .
H10B H 1.094590 -0.084296 0.223681 0.023 Uiso 1 1 calc R U . . .
C11 C 0.8893(3) 0.0358(3) 0.17045(12) 0.0179(4) Uani 1 1 d . . . . .
C12 C 0.6956(4) 0.0180(3) 0.13934(12) 0.0194(4) Uani 1 1 d . . . . .
H12 H 0.602176 -0.095182 0.138375 0.023 Uiso 1 1 calc R U . . .
C13 C 0.6389(3) 0.1662(3) 0.10966(12) 0.0180(4) Uani 1 1 d . . . . .
C14 C 0.7731(3) 0.3329(3) 0.11196(11) 0.0174(4) Uani 1 1 d . . . . .
C15 C 0.9689(3) 0.3480(3) 0.14132(12) 0.0172(4) Uani 1 1 d . . . . .
C16 C 1.0259(3) 0.1991(3) 0.17067(12) 0.0185(4) Uani 1 1 d . . . . .
H16 H 1.159282 0.209720 0.190959 0.022 Uiso 1 1 calc R U . . .
C17 C 0.3113(4) -0.0058(4) 0.06992(16) 0.0304(6) Uani 1 1 d . . . . .
H17A H 0.185835 0.009152 0.044394 0.046 Uiso 1 1 calc R U . . .
H17B H 0.293249 -0.049321 0.117379 0.046 Uiso 1 1 calc R U . . .
H17C H 0.357461 -0.094209 0.042889 0.046 Uiso 1 1 calc R U . . .
C18 C 0.7597(5) 0.5439(4) 0.02284(15) 0.0353(7) Uani 1 1 d . . . . .
H18A H 0.728629 0.440705 -0.012322 0.053 Uiso 1 1 calc R U . . .
H18B H 0.900795 0.601520 0.028951 0.053 Uiso 1 1 calc R U . . .
H18C H 0.684896 0.632267 0.006019 0.053 Uiso 1 1 calc R U . . .
C19 C 1.2944(4) 0.5318(3) 0.16855(14) 0.0241(5) Uani 1 1 d . . . . .
H19A H 1.346542 0.446827 0.142065 0.036 Uiso 1 1 calc R U . . .
H19B H 1.306354 0.504422 0.219114 0.036 Uiso 1 1 calc R U . . .
H19C H 1.369230 0.656226 0.164009 0.036 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 1.216(3) . ?
O2 C2 1.228(3) . ?
O3 C5 1.233(3) . ?
O4 C5 1.247(3) . ?
N1 H1 0.8800 . ?
N1 C1 1.386(3) . ?
N1 C2 1.355(3) . ?
N2 H2 0.8800 . ?
N2 C2 1.355(3) . ?
N2 C3 1.368(3) . ?
C1 C4 1.441(3) . ?
C3 C4 1.335(3) . ?
C3 C5 1.516(3) . ?
C4 H4 0.9500 . ?
O5 C13 1.368(3) . ?
O5 C17 1.415(3) . ?
O6 C14 1.373(2) . ?
O6 C18 1.421(3) . ?
O7 C15 1.356(3) . ?
O7 C19 1.430(3) . ?
N3 H3 0.8800 . ?
N3 C6 1.357(3) . ?
N3 C9 1.358(3) . ?
N4 C8 1.334(3) . ?
N4 C9 1.328(3) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C9 1.306(3) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N6 C8 1.317(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.350(3) . ?
C7 C8 1.440(3) . ?
C7 C10 1.498(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.508(3) . ?
C11 C12 1.385(3) . ?
C11 C16 1.380(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(3) . ?
C13 C14 1.387(3) . ?
C14 C15 1.393(3) . ?
C15 C16 1.388(3) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1 116.7 . . ?
C2 N1 H1 116.7 . . ?
C2 N1 C1 126.63(19) . . ?
C2 N2 H2 118.4 . . ?
C2 N2 C3 123.20(19) . . ?
C3 N2 H2 118.4 . . ?
O1 C1 N1 119.7(2) . . ?
O1 C1 C4 126.3(2) . . ?
N1 C1 C4 114.04(19) . . ?
O2 C2 N1 122.25(19) . . ?
O2 C2 N2 122.6(2) . . ?
N1 C2 N2 115.2(2) . . ?
N2 C3 C5 114.65(19) . . ?
C4 C3 N2 120.6(2) . . ?
C4 C3 C5 124.7(2) . . ?
C1 C4 H4 119.9 . . ?
C3 C4 C1 120.3(2) . . ?
C3 C4 H4 119.9 . . ?
O3 C5 O4 128.3(2) . . ?
O3 C5 C3 118.6(2) . . ?
O4 C5 C3 113.1(2) . . ?
C13 O5 C17 117.47(18) . . ?
C14 O6 C18 115.19(19) . . ?
C15 O7 C19 116.69(17) . . ?
C6 N3 H3 120.3 . . ?
C6 N3 C9 119.42(18) . . ?
C9 N3 H3 120.3 . . ?
C9 N4 C8 118.83(19) . . ?
H5A N5 H5B 120.0 . . ?
C9 N5 H5A 120.0 . . ?
C9 N5 H5B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C8 N6 H6A 120.0 . . ?
C8 N6 H6B 120.0 . . ?
N3 C6 H6 119.0 . . ?
C7 C6 N3 122.0(2) . . ?
C7 C6 H6 119.0 . . ?
C6 C7 C8 115.6(2) . . ?
C6 C7 C10 121.7(2) . . ?
C8 C7 C10 122.52(19) . . ?
N4 C8 C7 122.01(19) . . ?
N6 C8 N4 116.1(2) . . ?
N6 C8 C7 121.83(19) . . ?
N4 C9 N3 122.13(19) . . ?
N5 C9 N3 118.48(19) . . ?
N5 C9 N4 119.4(2) . . ?
C7 C10 H10A 108.4 . . ?
C7 C10 H10B 108.4 . . ?
C7 C10 C11 115.64(19) . . ?
H10A C10 H10B 107.4 . . ?
C11 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C12 C11 C10 120.2(2) . . ?
C16 C11 C10 119.5(2) . . ?
C16 C11 C12 120.22(19) . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.6(2) . . ?
C13 C12 H12 120.2 . . ?
O5 C13 C12 124.3(2) . . ?
O5 C13 C14 114.98(19) . . ?
C12 C13 C14 120.7(2) . . ?
O6 C14 C13 119.4(2) . . ?
O6 C14 C15 121.19(19) . . ?
C13 C14 C15 119.25(19) . . ?
O7 C15 C14 115.74(18) . . ?
O7 C15 C16 124.3(2) . . ?
C16 C15 C14 119.9(2) . . ?
C11 C16 C15 120.2(2) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O6 C18 H18A 109.5 . . ?
O6 C18 H18B 109.5 . . ?
O6 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O7 C19 H19A 109.5 . . ?
O7 C19 H19B 109.5 . . ?
O7 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 C4 C3 178.1(2) . . . . ?
N1 C1 C4 C3 -1.8(3) . . . . ?
N2 C3 C4 C1 1.0(3) . . . . ?
N2 C3 C5 O3 -173.8(2) . . . . ?
N2 C3 C5 O4 6.4(3) . . . . ?
C1 N1 C2 O2 178.5(2) . . . . ?
C1 N1 C2 N2 -1.1(3) . . . . ?
C2 N1 C1 O1 -178.0(2) . . . . ?
C2 N1 C1 C4 1.9(3) . . . . ?
C2 N2 C3 C4 -0.2(4) . . . . ?
C2 N2 C3 C5 179.8(2) . . . . ?
C3 N2 C2 O2 -179.5(2) . . . . ?
C3 N2 C2 N1 0.2(3) . . . . ?
C4 C3 C5 O3 6.3(4) . . . . ?
C4 C3 C5 O4 -173.6(2) . . . . ?
C5 C3 C4 C1 -179.0(2) . . . . ?
O5 C13 C14 O6 6.5(3) . . . . ?
O5 C13 C14 C15 -177.4(2) . . . . ?
O6 C14 C15 O7 -5.6(3) . . . . ?
O6 C14 C15 C16 173.2(2) . . . . ?
O7 C15 C16 C11 179.0(2) . . . . ?
N3 C6 C7 C8 -0.5(3) . . . . ?
N3 C6 C7 C10 174.0(2) . . . . ?
C6 N3 C9 N4 3.2(3) . . . . ?
C6 N3 C9 N5 -176.0(2) . . . . ?
C6 C7 C8 N4 2.5(3) . . . . ?
C6 C7 C8 N6 179.6(2) . . . . ?
C6 C7 C10 C11 126.1(2) . . . . ?
C7 C10 C11 C12 -58.7(3) . . . . ?
C7 C10 C11 C16 120.6(2) . . . . ?
C8 N4 C9 N3 -1.1(3) . . . . ?
C8 N4 C9 N5 178.1(2) . . . . ?
C8 C7 C10 C11 -59.9(3) . . . . ?
C9 N3 C6 C7 -2.3(3) . . . . ?
C9 N4 C8 N6 -179.0(2) . . . . ?
C9 N4 C8 C7 -1.8(3) . . . . ?
C10 C7 C8 N4 -171.9(2) . . . . ?
C10 C7 C8 N6 5.2(3) . . . . ?
C10 C11 C12 C13 178.0(2) . . . . ?
C10 C11 C16 C15 -177.6(2) . . . . ?
C11 C12 C13 O5 179.5(2) . . . . ?
C11 C12 C13 C14 -1.2(3) . . . . ?
C12 C11 C16 C15 1.6(3) . . . . ?
C12 C13 C14 O6 -172.8(2) . . . . ?
C12 C13 C14 C15 3.2(3) . . . . ?
C13 C14 C15 O7 178.4(2) . . . . ?
C13 C14 C15 C16 -2.8(3) . . . . ?
C14 C15 C16 C11 0.4(3) . . . . ?
C16 C11 C12 C13 -1.2(3) . . . . ?
C17 O5 C13 C12 -4.0(3) . . . . ?
C17 O5 C13 C14 176.7(2) . . . . ?
C18 O6 C14 C13 -107.4(3) . . . . ?
C18 O6 C14 C15 76.6(3) . . . . ?
C19 O7 C15 C14 -178.7(2) . . . . ?
C19 O7 C15 C16 2.6(3) . . . . ?

_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 2.422
_oxdiff_exptl_absorpt_empirical_full_min 0.619
####################################################################### 
# 
# 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_r20210921c
_database_code_depnum_ccdc_archive 'CCDC 2221421'
loop_
_audit_author_name
_audit_author_address
xingchenhu
;Tianjin university
China
;
_audit_update_record             
;
2023-03-17 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;
_audit_creation_date             2023-03-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H19 N4 O3, C7 H5 O4'
_chemical_formula_sum            'C21 H24 N4 O7'
_chemical_formula_weight         444.44
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.0172(3)
_cell_length_b                   28.2186(13)
_cell_length_c                   10.7877(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.469(5)
_cell_angle_gamma                90
_cell_volume                     2077.38(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7215
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      31.3890
_cell_measurement_theta_min      2.0640
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70873
_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            ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_av_unetI/netI     0.0772
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26572
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.257
_diffrn_reflns_theta_min         2.071
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   1.00    1.00    --  -30.00  45.00   0.00  180
  2  ω   -120.00  60.00   1.00    1.00    --  -30.00  45.00  90.00  180
  3  ω   -120.00  60.00   1.00    1.00    --  -30.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4341
_reflns_number_total             6989
_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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.0115(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         6989
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0659
_refine_ls_restrained_S_all      1.040
_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)+(0.0548P)²+0.7520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1671
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C5(H5), C7(H7), C14(H14), C16(H16), C19(H19), C20(H20)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N4(H4A,H4B)
2.d Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 -0.1161(2) 0.20960(5) 0.13265(13) 0.0323(3) Uani 1 1 d . . . . .
O2 O 0.2286(2) 0.18729(5) 0.28361(12) 0.0280(3) Uani 1 1 d . . . . .
O3 O 0.53642(19) 0.24670(5) 0.31870(13) 0.0290(3) Uani 1 1 d . . . . .
N1 N 0.3453(3) 0.34326(6) -0.13254(17) 0.0341(4) Uani 1 1 d . . . . .
H1A H 0.412433 0.334181 -0.187826 0.041 Uiso 1 1 calc R U . . .
H1B H 0.236850 0.328304 -0.128464 0.041 Uiso 1 1 calc R U . . .
N2 N 0.5747(2) 0.40080(5) -0.06665(16) 0.0265(3) Uani 1 1 d . . . . .
N3 N 0.5428(2) 0.45415(5) 0.09588(15) 0.0243(3) Uani 1 1 d . . . . .
H3 H 0.589780 0.478441 0.144638 0.029 Uiso 1 1 calc R U . . .
N4 N 0.7988(2) 0.46144(6) -0.00303(16) 0.0295(4) Uani 1 1 d . . . . .
H4A H 0.864603 0.452191 -0.058926 0.035 Uiso 1 1 calc R U . . .
H4B H 0.839277 0.486053 0.046143 0.035 Uiso 1 1 calc R U . . .
C1 C -0.3005(3) 0.21862(8) 0.04669(19) 0.0337(5) Uani 1 1 d . . . . .
H1C H -0.361358 0.246512 0.075469 0.050 Uiso 1 1 calc R U . . .
H1D H -0.386323 0.191086 0.044523 0.050 Uiso 1 1 calc R U . . .
H1E H -0.280246 0.224431 -0.038885 0.050 Uiso 1 1 calc R U . . .
C2 C 0.0252(3) 0.24398(7) 0.14641(17) 0.0238(4) Uani 1 1 d . . . . .
C3 C 0.2068(3) 0.23085(6) 0.22343(17) 0.0239(4) Uani 1 1 d . . . . .
C4 C 0.3625(3) 0.26295(7) 0.24417(16) 0.0225(4) Uani 1 1 d . . . . .
C5 C 0.3349(3) 0.30817(6) 0.18935(17) 0.0233(4) Uani 1 1 d . . . . .
H5 H 0.439908 0.330268 0.204565 0.028 Uiso 1 1 calc R U . . .
C6 C 0.1543(3) 0.32071(6) 0.11286(17) 0.0225(4) Uani 1 1 d . . . . .
C7 C -0.0015(3) 0.28867(7) 0.09062(17) 0.0237(4) Uani 1 1 d . . . . .
H7 H -0.124773 0.297308 0.037837 0.028 Uiso 1 1 calc R U . . .
C8 C 0.2716(3) 0.14960(7) 0.20460(19) 0.0310(4) Uani 1 1 d . . . . .
H8A H 0.279593 0.119516 0.250916 0.046 Uiso 1 1 calc R U . . .
H8B H 0.397033 0.155918 0.182566 0.046 Uiso 1 1 calc R U . . .
H8C H 0.167473 0.147680 0.126463 0.046 Uiso 1 1 calc R U . . .
C9 C 0.6863(3) 0.28125(8) 0.3623(2) 0.0336(5) Uani 1 1 d . . . . .
H9A H 0.791985 0.267091 0.427390 0.050 Uiso 1 1 calc R U . . .
H9B H 0.631036 0.308306 0.398809 0.050 Uiso 1 1 calc R U . . .
H9C H 0.738612 0.292001 0.290380 0.050 Uiso 1 1 calc R U . . .
C10 C 0.1182(3) 0.36989(6) 0.05303(18) 0.0240(4) Uani 1 1 d . . . . .
H10A H 0.026231 0.366890 -0.031424 0.029 Uiso 1 1 calc R U . . .
H10B H 0.054075 0.389779 0.107102 0.029 Uiso 1 1 calc R U . . .
C11 C 0.3006(3) 0.39493(6) 0.03634(17) 0.0226(4) Uani 1 1 d . . . . .
C12 C 0.4077(3) 0.37964(6) -0.05500(18) 0.0242(4) Uani 1 1 d . . . . .
C13 C 0.6375(3) 0.43810(6) 0.00716(18) 0.0231(4) Uani 1 1 d . . . . .
C14 C 0.3750(2) 0.43239(6) 0.10871(17) 0.0218(3) Uani 1 1 d . . . . .
H14 H 0.309052 0.443949 0.170156 0.026 Uiso 1 1 calc R U . . .
O4 O 1.4366(2) 0.58523(7) 0.61568(15) 0.0499(5) Uani 1 1 d . . . . .
H4 H 1.496964 0.577543 0.559995 0.075 Uiso 1 1 calc R U . . .
O5 O 0.6365(2) 0.57047(7) 0.43382(16) 0.0451(4) Uani 1 1 d . . . . .
H5A H 0.608428 0.555716 0.364312 0.068 Uiso 1 1 calc R U . . .
O6 O 0.69224(19) 0.52716(5) 0.24398(14) 0.0332(3) Uani 1 1 d . . . . .
O7 O 0.9898(2) 0.52341(5) 0.20311(14) 0.0359(4) Uani 1 1 d . . . . .
C15 C 1.2389(3) 0.57993(8) 0.56729(19) 0.0331(5) Uani 1 1 d . . . . .
C16 C 1.1619(3) 0.55846(7) 0.45067(18) 0.0279(4) Uani 1 1 d . . . . .
H16 H 1.247792 0.545730 0.402928 0.033 Uiso 1 1 calc R U . . .
C17 C 0.9598(3) 0.55535(6) 0.40276(18) 0.0238(4) Uani 1 1 d . . . . .
C18 C 0.8354(3) 0.57315(7) 0.47596(19) 0.0302(4) Uani 1 1 d . . . . .
C19 C 0.9131(3) 0.59448(8) 0.5930(2) 0.0345(5) Uani 1 1 d . . . . .
H19 H 0.827846 0.606840 0.641768 0.041 Uiso 1 1 calc R U . . .
C20 C 1.1140(3) 0.59779(8) 0.6388(2) 0.0334(5) Uani 1 1 d . . . . .
H20 H 1.166513 0.612254 0.718981 0.040 Uiso 1 1 calc R U . . .
C21 C 0.8788(3) 0.53371(7) 0.27392(19) 0.0274(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.428(2) . ?
O1 C2 1.370(2) . ?
O2 C3 1.382(2) . ?
O2 C8 1.438(2) . ?
O3 C4 1.374(2) . ?
O3 C9 1.431(2) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C12 1.332(2) . ?
N2 C12 1.346(2) . ?
N2 C13 1.332(2) . ?
N3 H3 0.8800 . ?
N3 C13 1.364(2) . ?
N3 C14 1.364(2) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N4 C13 1.336(2) . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C2 C3 1.399(3) . ?
C2 C7 1.391(3) . ?
C3 C4 1.396(2) . ?
C4 C5 1.401(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(2) . ?
C6 C7 1.396(2) . ?
C6 C10 1.527(2) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.509(2) . ?
C11 C12 1.438(2) . ?
C11 C14 1.345(3) . ?
C14 H14 0.9500 . ?
O4 H4 0.8400 . ?
O4 C15 1.372(2) . ?
O5 H5A 0.8400 . ?
O5 C18 1.366(2) . ?
O6 C21 1.287(2) . ?
O7 C21 1.246(2) . ?
C15 C16 1.387(3) . ?
C15 C20 1.390(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.394(2) . ?
C17 C18 1.400(3) . ?
C17 C21 1.503(3) . ?
C18 C19 1.390(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(3) . ?
C20 H20 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 117.87(15) . . ?
C3 O2 C8 113.26(14) . . ?
C4 O3 C9 116.72(15) . . ?
H1A N1 H1B 120.0 . . ?
C12 N1 H1A 120.0 . . ?
C12 N1 H1B 120.0 . . ?
C13 N2 C12 117.97(15) . . ?
C13 N3 H3 120.1 . . ?
C14 N3 H3 120.1 . . ?
C14 N3 C13 119.70(15) . . ?
H4A N4 H4B 120.0 . . ?
C13 N4 H4A 120.0 . . ?
C13 N4 H4B 120.0 . . ?
O1 C1 H1C 109.5 . . ?
O1 C1 H1D 109.5 . . ?
O1 C1 H1E 109.5 . . ?
H1C C1 H1D 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
O1 C2 C3 114.37(16) . . ?
O1 C2 C7 125.01(17) . . ?
C7 C2 C3 120.62(16) . . ?
O2 C3 C2 120.03(16) . . ?
O2 C3 C4 120.32(16) . . ?
C4 C3 C2 119.57(17) . . ?
O3 C4 C3 115.62(16) . . ?
O3 C4 C5 124.57(16) . . ?
C3 C4 C5 119.82(16) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.05(16) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C7 120.49(17) . . ?
C5 C6 C10 121.46(16) . . ?
C7 C6 C10 118.03(16) . . ?
C2 C7 C6 119.44(17) . . ?
C2 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 108.6 . . ?
C6 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 C6 114.48(15) . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C12 C11 C10 122.31(16) . . ?
C14 C11 C10 121.58(16) . . ?
C14 C11 C12 116.08(16) . . ?
N1 C12 N2 116.69(16) . . ?
N1 C12 C11 120.90(17) . . ?
N2 C12 C11 122.41(16) . . ?
N2 C13 N3 122.31(16) . . ?
N2 C13 N4 120.63(16) . . ?
N4 C13 N3 117.06(16) . . ?
N3 C14 H14 119.3 . . ?
C11 C14 N3 121.49(16) . . ?
C11 C14 H14 119.3 . . ?
C15 O4 H4 109.5 . . ?
C18 O5 H5A 109.5 . . ?
O4 C15 C16 122.56(18) . . ?
O4 C15 C20 117.50(19) . . ?
C16 C15 C20 119.93(18) . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.75(17) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C18 118.84(17) . . ?
C16 C17 C21 120.08(16) . . ?
C18 C17 C21 121.07(16) . . ?
O5 C18 C17 121.05(17) . . ?
O5 C18 C19 118.70(17) . . ?
C19 C18 C17 120.24(17) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.28(18) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 120.0 . . ?
C19 C20 C15 119.93(19) . . ?
C19 C20 H20 120.0 . . ?
O6 C21 C17 115.72(16) . . ?
O7 C21 O6 123.89(18) . . ?
O7 C21 C17 120.39(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 O2 -3.4(2) . . . . ?
O1 C2 C3 C4 179.82(15) . . . . ?
O1 C2 C7 C6 179.56(16) . . . . ?
O2 C3 C4 O3 4.6(2) . . . . ?
O2 C3 C4 C5 -175.80(15) . . . . ?
O3 C4 C5 C6 178.39(16) . . . . ?
C1 O1 C2 C3 -174.66(16) . . . . ?
C1 O1 C2 C7 5.3(3) . . . . ?
C2 C3 C4 O3 -178.63(15) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C2 C7 C6 -0.5(3) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C4 C5 C6 C10 179.17(16) . . . . ?
C5 C6 C7 C2 0.3(3) . . . . ?
C5 C6 C10 C11 24.2(2) . . . . ?
C6 C10 C11 C12 69.7(2) . . . . ?
C6 C10 C11 C14 -108.7(2) . . . . ?
C7 C2 C3 O2 176.64(15) . . . . ?
C7 C2 C3 C4 -0.1(3) . . . . ?
C7 C6 C10 C11 -157.14(16) . . . . ?
C8 O2 C3 C2 85.2(2) . . . . ?
C8 O2 C3 C4 -98.05(19) . . . . ?
C9 O3 C4 C3 -168.06(16) . . . . ?
C9 O3 C4 C5 12.4(2) . . . . ?
C10 C6 C7 C2 -178.39(15) . . . . ?
C10 C11 C12 N1 2.4(3) . . . . ?
C10 C11 C12 N2 -177.37(17) . . . . ?
C10 C11 C14 N3 178.16(16) . . . . ?
C12 N2 C13 N3 2.3(3) . . . . ?
C12 N2 C13 N4 -177.87(17) . . . . ?
C12 C11 C14 N3 -0.4(3) . . . . ?
C13 N2 C12 N1 178.14(17) . . . . ?
C13 N2 C12 C11 -2.1(3) . . . . ?
C13 N3 C14 C11 0.6(3) . . . . ?
C14 N3 C13 N2 -1.6(3) . . . . ?
C14 N3 C13 N4 178.57(16) . . . . ?
C14 C11 C12 N1 -179.12(18) . . . . ?
C14 C11 C12 N2 1.1(3) . . . . ?
O4 C15 C16 C17 -177.6(2) . . . . ?
O4 C15 C20 C19 178.4(2) . . . . ?
O5 C18 C19 C20 179.9(2) . . . . ?
C15 C16 C17 C18 -1.7(3) . . . . ?
C15 C16 C17 C21 177.57(18) . . . . ?
C16 C15 C20 C19 -0.5(3) . . . . ?
C16 C17 C18 O5 -179.27(19) . . . . ?
C16 C17 C18 C19 1.4(3) . . . . ?
C16 C17 C21 O6 172.02(17) . . . . ?
C16 C17 C21 O7 -8.2(3) . . . . ?
C17 C18 C19 C20 -0.8(3) . . . . ?
C18 C17 C21 O6 -8.7(3) . . . . ?
C18 C17 C21 O7 171.03(19) . . . . ?
C18 C19 C20 C15 0.3(3) . . . . ?
C20 C15 C16 C17 1.3(3) . . . . ?
C21 C17 C18 O5 1.5(3) . . . . ?
C21 C17 C18 C19 -177.82(19) . . . . ?

_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
;
####################################################################### 
# 
# 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_r20220722b
_database_code_depnum_ccdc_archive 'CCDC 2221430'
loop_
_audit_author_name
_audit_author_address
XingchenHu
;CCDC
China
;
_audit_update_record             
;
2022-11-22 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;
_audit_creation_date             2022-08-02
_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        TMP-26HBA
_chemical_formula_moiety         'C14 H19 N4 O3, C7 H5 O4'
_chemical_formula_sum            'C21 H24 N4 O7'
_chemical_formula_weight         444.44
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.4626(13)
_cell_length_b                   9.2831(4)
_cell_length_c                   19.5540(11)
_cell_angle_alpha                90
_cell_angle_beta                 111.922(6)
_cell_angle_gamma                90
_cell_volume                     4287.8(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7323
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      31.9390
_cell_measurement_theta_min      2.2610
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79737
_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            ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            23814
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.258
_diffrn_reflns_theta_min         2.264
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   1.00    1.00    --  -30.00  45.00   0.00  180
  2  ω   -120.00  30.00   1.00    1.00    --  -30.00  45.00  90.00  150
  3  ω   -120.00  30.00   1.00    1.00    --  -30.00  45.00 180.00  150
;
_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      0.0245209000
_diffrn_orient_matrix_UB_12      0.0425244000
_diffrn_orient_matrix_UB_13      0.0063614000
_diffrn_orient_matrix_UB_21      0.0169500000
_diffrn_orient_matrix_UB_22      -0.0630752000
_diffrn_orient_matrix_UB_23      0.0084627000
_diffrn_orient_matrix_UB_31      -0.0037056000
_diffrn_orient_matrix_UB_32      -0.0069969000
_diffrn_orient_matrix_UB_33      -0.0376406000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4306
_reflns_number_total             7029
_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         0.269
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0023(3)
_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   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         7029
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0603
_refine_ls_restrained_S_all      1.059
_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)+(0.0549P)²+1.5795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1585
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C9(H9), C14(H14), C16(H16), C17(H17), C18(H18)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N4(H4A,H4B)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2C,H2D,H2E), C3(H3A,H3B,H3C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.61315(5) 0.87024(13) 0.66582(6) 0.0363(3) Uani 1 1 d . . . . .
O2 O 0.52323(5) 0.72074(13) 0.66569(6) 0.0338(3) Uani 1 1 d . . . . .
O3 O 0.44378(5) 0.62598(13) 0.53978(6) 0.0352(3) Uani 1 1 d . . . . .
N1 N 0.61960(6) 0.63978(15) 0.34941(8) 0.0353(3) Uani 1 1 d . . . . .
H1 H 0.633393 0.553414 0.364272 0.042 Uiso 1 1 calc R U . . .
N2 N 0.66417(7) 0.63847(16) 0.26652(9) 0.0457(4) Uani 1 1 d . . . . .
H2A H 0.672996 0.679300 0.231621 0.055 Uiso 1 1 calc R U . . .
H2B H 0.676603 0.551371 0.282041 0.055 Uiso 1 1 calc R U . . .
N3 N 0.61302(6) 0.84042(15) 0.27254(8) 0.0322(3) Uani 1 1 d . . . . .
N4 N 0.56806(6) 1.04471(15) 0.28506(8) 0.0333(3) Uani 1 1 d . . . . .
H4A H 0.578622 1.084902 0.251486 0.040 Uiso 1 1 calc R U . . .
H4B H 0.548008 1.094238 0.305076 0.040 Uiso 1 1 calc R U . . .
C1 C 0.66145(8) 0.9520(2) 0.66704(12) 0.0457(5) Uani 1 1 d . . . . .
H1A H 0.681651 0.898323 0.641249 0.069 Uiso 1 1 calc R U . . .
H1B H 0.686818 0.968575 0.718237 0.069 Uiso 1 1 calc R U . . .
H1C H 0.648819 1.044717 0.642455 0.069 Uiso 1 1 calc R U . . .
C2 C 0.55191(11) 0.5917(2) 0.69938(12) 0.0559(6) Uani 1 1 d . . . . .
H2C H 0.531946 0.508168 0.670787 0.084 Uiso 1 1 calc R U . . .
H2D H 0.552692 0.584812 0.749765 0.084 Uiso 1 1 calc R U . . .
H2E H 0.590757 0.593706 0.700699 0.084 Uiso 1 1 calc R U . . .
C3 C 0.39919(8) 0.5824(2) 0.47332(10) 0.0420(4) Uani 1 1 d . . . . .
H3A H 0.381098 0.667874 0.444820 0.063 Uiso 1 1 calc R U . . .
H3B H 0.371099 0.526804 0.485422 0.063 Uiso 1 1 calc R U . . .
H3C H 0.414765 0.522664 0.444107 0.063 Uiso 1 1 calc R U . . .
C4 C 0.57307(7) 0.83722(17) 0.59794(9) 0.0275(3) Uani 1 1 d . . . . .
C5 C 0.52790(7) 0.75283(16) 0.59896(8) 0.0267(3) Uani 1 1 d . . . . .
C6 C 0.48524(6) 0.71140(16) 0.53284(9) 0.0268(3) Uani 1 1 d . . . . .
C7 C 0.48626(7) 0.76223(17) 0.46591(9) 0.0295(3) Uani 1 1 d . . . . .
H7 H 0.457199 0.735269 0.420741 0.035 Uiso 1 1 calc R U . . .
C8 C 0.52985(7) 0.85219(17) 0.46562(9) 0.0292(3) Uani 1 1 d . . . . .
C9 C 0.57405(7) 0.88734(17) 0.53119(9) 0.0304(3) Uani 1 1 d . . . . .
H9 H 0.604650 0.945041 0.530456 0.036 Uiso 1 1 calc R U . . .
C10 C 0.52916(8) 0.91815(19) 0.39441(9) 0.0342(4) Uani 1 1 d . . . . .
H10A H 0.489650 0.919319 0.358309 0.041 Uiso 1 1 calc R U . . .
H10B H 0.542078 1.019354 0.404034 0.041 Uiso 1 1 calc R U . . .
C11 C 0.56566(7) 0.84068(17) 0.36044(9) 0.0292(3) Uani 1 1 d . . . . .
C12 C 0.58246(7) 0.90848(17) 0.30564(9) 0.0289(3) Uani 1 1 d . . . . .
C13 C 0.63197(7) 0.70851(18) 0.29584(10) 0.0333(4) Uani 1 1 d . . . . .
C14 C 0.58563(7) 0.70570(18) 0.38000(10) 0.0330(4) Uani 1 1 d . . . . .
H14 H 0.575796 0.655525 0.415864 0.040 Uiso 1 1 calc R U . . .
O4 O 0.77562(6) 0.18705(16) 0.32980(8) 0.0527(4) Uani 1 1 d . . . . .
H4 H 0.762165 0.270737 0.324894 0.079 Uiso 1 1 calc R U . . .
O5 O 0.65305(6) 0.13453(14) 0.46466(8) 0.0472(4) Uani 1 1 d . . . . .
H5 H 0.644200 0.219060 0.449380 0.071 Uiso 1 1 calc R U . . .
O6 O 0.71851(7) 0.39432(15) 0.34240(9) 0.0577(4) Uani 1 1 d . . . . .
O7 O 0.65806(6) 0.37171(13) 0.39990(8) 0.0463(4) Uani 1 1 d . . . . .
C15 C 0.75222(7) 0.1056(2) 0.36869(10) 0.0375(4) Uani 1 1 d . . . . .
C16 C 0.76641(8) -0.0389(2) 0.38031(11) 0.0453(5) Uani 1 1 d . . . . .
H16 H 0.791523 -0.081219 0.360311 0.054 Uiso 1 1 calc R U . . .
C17 C 0.74352(8) -0.1206(2) 0.42140(12) 0.0486(5) Uani 1 1 d . . . . .
H17 H 0.753324 -0.219636 0.429567 0.058 Uiso 1 1 calc R U . . .
C18 C 0.70669(8) -0.0619(2) 0.45093(11) 0.0453(5) Uani 1 1 d . . . . .
H18 H 0.692206 -0.119513 0.480037 0.054 Uiso 1 1 calc R U . . .
C19 C 0.69103(7) 0.08207(19) 0.43771(10) 0.0360(4) Uani 1 1 d . . . . .
C20 C 0.71371(7) 0.16858(19) 0.39641(9) 0.0325(4) Uani 1 1 d . . . . .
C21 C 0.69577(8) 0.3206(2) 0.37888(11) 0.0388(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.438(2) . ?
O1 C4 1.373(2) . ?
O2 C2 1.429(2) . ?
O2 C5 1.3861(18) . ?
O3 C3 1.428(2) . ?
O3 C6 1.3669(18) . ?
N1 H1 0.8800 . ?
N1 C13 1.360(2) . ?
N1 C14 1.3664(19) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C13 1.332(2) . ?
N3 C12 1.342(2) . ?
N3 C13 1.333(2) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N4 C12 1.336(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2C 0.9800 . ?
C2 H2D 0.9800 . ?
C2 H2E 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.398(2) . ?
C4 C9 1.395(2) . ?
C5 C6 1.397(2) . ?
C6 C7 1.401(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.391(2) . ?
C8 C9 1.393(2) . ?
C8 C10 1.515(2) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.511(2) . ?
C11 C12 1.439(2) . ?
C11 C14 1.353(2) . ?
C14 H14 0.9500 . ?
O4 H4 0.8400 . ?
O4 C15 1.357(2) . ?
O5 H5 0.8400 . ?
O5 C19 1.353(2) . ?
O6 C21 1.273(2) . ?
O7 C21 1.2691(19) . ?
C15 C16 1.386(3) . ?
C15 C20 1.412(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.391(2) . ?
C19 C20 1.407(2) . ?
C20 C21 1.484(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
C4 O1 C1 117.14(13) . . ?
C5 O2 C2 113.91(13) . . ?
C6 O3 C3 117.06(13) . . ?
C13 N1 H1 120.2 . . ?
C13 N1 C14 119.57(14) . . ?
C14 N1 H1 120.2 . . ?
H2A N2 H2B 120.0 . . ?
C13 N2 H2A 120.0 . . ?
C13 N2 H2B 120.0 . . ?
C13 N3 C12 117.96(13) . . ?
H4A N4 H4B 120.0 . . ?
C12 N4 H4A 120.0 . . ?
C12 N4 H4B 120.0 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 H2C 109.5 . . ?
O2 C2 H2D 109.5 . . ?
O2 C2 H2E 109.5 . . ?
H2C C2 H2D 109.5 . . ?
H2C C2 H2E 109.5 . . ?
H2D C2 H2E 109.5 . . ?
O3 C3 H3A 109.5 . . ?
O3 C3 H3B 109.5 . . ?
O3 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C4 C5 115.45(14) . . ?
O1 C4 C9 124.31(15) . . ?
C9 C4 C5 120.17(15) . . ?
O2 C5 C4 119.60(14) . . ?
O2 C5 C6 120.12(14) . . ?
C6 C5 C4 120.06(14) . . ?
O3 C6 C5 115.49(13) . . ?
O3 C6 C7 124.94(14) . . ?
C5 C6 C7 119.52(14) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 119.97(15) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C9 120.58(15) . . ?
C7 C8 C10 120.73(15) . . ?
C9 C8 C10 118.65(15) . . ?
C4 C9 H9 120.2 . . ?
C8 C9 C4 119.52(15) . . ?
C8 C9 H9 120.2 . . ?
C8 C10 H10A 108.7 . . ?
C8 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 C8 114.43(13) . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C12 C11 C10 121.46(14) . . ?
C14 C11 C10 122.99(14) . . ?
C14 C11 C12 115.53(14) . . ?
N3 C12 C11 122.73(14) . . ?
N4 C12 N3 116.34(14) . . ?
N4 C12 C11 120.93(14) . . ?
N2 C13 N1 117.33(15) . . ?
N2 C13 N3 120.24(15) . . ?
N3 C13 N1 122.42(14) . . ?
N1 C14 H14 119.2 . . ?
C11 C14 N1 121.58(14) . . ?
C11 C14 H14 119.2 . . ?
C15 O4 H4 109.5 . . ?
C19 O5 H5 109.5 . . ?
O4 C15 C16 119.25(16) . . ?
O4 C15 C20 119.84(16) . . ?
C16 C15 C20 120.91(17) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.07(18) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.67(18) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.53(19) . . ?
C19 C18 H18 120.2 . . ?
O5 C19 C18 118.05(17) . . ?
O5 C19 C20 121.63(15) . . ?
C18 C19 C20 120.31(17) . . ?
C15 C20 C21 120.20(15) . . ?
C19 C20 C15 118.48(16) . . ?
C19 C20 C21 121.25(15) . . ?
O6 C21 C20 118.40(15) . . ?
O7 C21 O6 122.56(17) . . ?
O7 C21 C20 119.04(15) . . ?

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 C4 C5 O2 6.3(2) . . . . ?
O1 C4 C5 C6 -179.07(13) . . . . ?
O1 C4 C9 C8 -177.20(14) . . . . ?
O2 C5 C6 O3 -7.0(2) . . . . ?
O2 C5 C6 C7 170.72(13) . . . . ?
O3 C6 C7 C8 178.10(14) . . . . ?
C1 O1 C4 C5 177.55(14) . . . . ?
C1 O1 C4 C9 -5.4(2) . . . . ?
C2 O2 C5 C4 -89.60(19) . . . . ?
C2 O2 C5 C6 95.77(19) . . . . ?
C3 O3 C6 C5 179.52(14) . . . . ?
C3 O3 C6 C7 1.9(2) . . . . ?
C4 C5 C6 O3 178.38(13) . . . . ?
C4 C5 C6 C7 -3.9(2) . . . . ?
C5 C4 C9 C8 -0.3(2) . . . . ?
C5 C6 C7 C8 0.6(2) . . . . ?
C6 C7 C8 C9 2.9(2) . . . . ?
C6 C7 C8 C10 -174.92(14) . . . . ?
C7 C8 C9 C4 -3.0(2) . . . . ?
C7 C8 C10 C11 -99.38(18) . . . . ?
C8 C10 C11 C12 -162.53(16) . . . . ?
C8 C10 C11 C14 16.1(2) . . . . ?
C9 C4 C5 O2 -170.90(14) . . . . ?
C9 C4 C5 C6 3.7(2) . . . . ?
C9 C8 C10 C11 82.77(19) . . . . ?
C10 C8 C9 C4 174.81(14) . . . . ?
C10 C11 C12 N3 -177.39(15) . . . . ?
C10 C11 C12 N4 2.6(3) . . . . ?
C10 C11 C14 N1 -178.52(16) . . . . ?
C12 N3 C13 N1 2.5(3) . . . . ?
C12 N3 C13 N2 -177.64(16) . . . . ?
C12 C11 C14 N1 0.2(2) . . . . ?
C13 N1 C14 C11 -2.7(3) . . . . ?
C13 N3 C12 N4 174.76(15) . . . . ?
C13 N3 C12 C11 -5.2(2) . . . . ?
C14 N1 C13 N2 -178.46(16) . . . . ?
C14 N1 C13 N3 1.4(3) . . . . ?
C14 C11 C12 N3 3.9(2) . . . . ?
C14 C11 C12 N4 -176.11(16) . . . . ?
O4 C15 C16 C17 178.50(18) . . . . ?
O4 C15 C20 C19 -178.79(16) . . . . ?
O4 C15 C20 C21 4.2(3) . . . . ?
O5 C19 C20 C15 -178.64(16) . . . . ?
O5 C19 C20 C21 -1.6(3) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C15 C20 C21 O6 -4.2(3) . . . . ?
C15 C20 C21 O7 174.93(17) . . . . ?
C16 C15 C20 C19 1.5(3) . . . . ?
C16 C15 C20 C21 -175.54(17) . . . . ?
C16 C17 C18 C19 1.6(3) . . . . ?
C17 C18 C19 O5 177.16(17) . . . . ?
C17 C18 C19 C20 -1.8(3) . . . . ?
C18 C19 C20 C15 0.3(3) . . . . ?
C18 C19 C20 C21 177.33(18) . . . . ?
C19 C20 C21 O6 178.80(18) . . . . ?
C19 C20 C21 O7 -2.0(3) . . . . ?
C20 C15 C16 C17 -1.8(3) . . . . ?

_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 1.311
_oxdiff_exptl_absorpt_empirical_full_min 0.822
####################################################################### 
# 
# 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_r20220721c
_database_code_depnum_ccdc_archive 'CCDC 2221425'
loop_
_audit_author_name
_audit_author_address
XingchenHu
;CCDC
China
;
_audit_update_record             
;
2022-11-22 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;
_audit_creation_date             2022-08-01
_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        TMP-GA-2MeOH
_chemical_formula_moiety         'C14 H19 N4 O3, C7 H5 O5, 2(C H4 O)'
_chemical_formula_sum            'C23 H32 N4 O10'
_chemical_formula_weight         524.52
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.2636(10)
_cell_length_b                   20.7045(13)
_cell_length_c                   12.0759(11)
_cell_angle_alpha                90
_cell_angle_beta                 117.535(11)
_cell_angle_gamma                90
_cell_volume                     2497.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6758
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      33.0010
_cell_measurement_theta_min      1.9630
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61810
_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            ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19767
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         1.967
_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 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   1.00    2.00    --  -30.00  45.00   0.00  180
  2  ω   -120.00  30.00   1.00    2.00    --  -30.00  45.00  90.00  150
  3  ω   -120.00   0.00   1.00    2.00    --  -30.00  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      0.0099420000
_diffrn_orient_matrix_UB_12      0.0222879000
_diffrn_orient_matrix_UB_13      0.0481536000
_diffrn_orient_matrix_UB_21      0.0244699000
_diffrn_orient_matrix_UB_22      0.0231120000
_diffrn_orient_matrix_UB_23      -0.0277822000
_diffrn_orient_matrix_UB_31      -0.0659201000
_diffrn_orient_matrix_UB_32      0.0119267000
_diffrn_orient_matrix_UB_33      -0.0360106000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3552
_reflns_number_total             5092
_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         0.276
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0059(9)
_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   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5092
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0560
_refine_ls_restrained_S_all      1.054
_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)+(0.0570P)²+0.6353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1473
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C8(H8), C12(H12), C17(H17), C21(H21)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N4(H4A,H4B)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2C,H2D,H2E), C3(H3A,H3B,H3C), C22(H22A,H22B,H22C),
 C23(H23A,H23B,H23C)
2.e Idealised tetrahedral OH refined as rotating group:
 O6(H6A), O7(H7), O8(H8A), O9(H9), O10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.03382(17) 0.52996(8) 0.25019(15) 0.0312(4) Uani 1 1 d . . . . .
O2 O -0.15565(16) 0.43031(8) 0.28584(14) 0.0280(4) Uani 1 1 d . . . . .
O3 O 0.22691(17) 0.55646(8) 0.40680(16) 0.0354(5) Uani 1 1 d . . . . .
N1 N 0.62592(19) 0.35673(9) 0.83760(16) 0.0247(5) Uani 1 1 d . . . . .
H1 H 0.692142 0.338030 0.830341 0.030 Uiso 1 1 calc R U . . .
N2 N 0.77813(19) 0.40530(10) 1.01929(18) 0.0290(5) Uani 1 1 d . . . . .
H2A H 0.797961 0.431896 1.082274 0.035 Uiso 1 1 calc R U . . .
H2B H 0.842254 0.384143 1.012570 0.035 Uiso 1 1 calc R U . . .
N3 N 0.55486(19) 0.42943(9) 0.94544(16) 0.0222(4) Uani 1 1 d . . . . .
N4 N 0.3355(2) 0.45662(10) 0.86716(18) 0.0289(5) Uani 1 1 d . . . . .
H4A H 0.359597 0.484218 0.929263 0.035 Uiso 1 1 calc R U . . .
H4B H 0.250613 0.452938 0.812055 0.035 Uiso 1 1 calc R U . . .
C1 C 0.0107(3) 0.53068(15) 0.1562(2) 0.0414(7) Uani 1 1 d . . . . .
H1A H -0.057463 0.551389 0.080487 0.062 Uiso 1 1 calc R U . . .
H1B H 0.025023 0.486262 0.137018 0.062 Uiso 1 1 calc R U . . .
H1C H 0.094736 0.554869 0.187111 0.062 Uiso 1 1 calc R U . . .
C2 C -0.2329(3) 0.38254(13) 0.3099(2) 0.0326(6) Uani 1 1 d . . . . .
H2C H -0.324761 0.382589 0.241742 0.049 Uiso 1 1 calc R U . . .
H2D H -0.233994 0.392503 0.388758 0.049 Uiso 1 1 calc R U . . .
H2E H -0.192815 0.339872 0.315632 0.049 Uiso 1 1 calc R U . . .
C3 C 0.3683(3) 0.56144(14) 0.4589(3) 0.0376(7) Uani 1 1 d . . . . .
H3A H 0.391352 0.599829 0.425336 0.056 Uiso 1 1 calc R U . . .
H3B H 0.403619 0.522860 0.437295 0.056 Uiso 1 1 calc R U . . .
H3C H 0.407427 0.565083 0.549896 0.056 Uiso 1 1 calc R U . . .
C4 C 0.0406(2) 0.49016(11) 0.3513(2) 0.0231(5) Uani 1 1 d . . . . .
C5 C -0.0241(2) 0.43836(11) 0.3739(2) 0.0216(5) Uani 1 1 d . . . . .
C6 C 0.0429(2) 0.39915(11) 0.4773(2) 0.0236(5) Uani 1 1 d . . . . .
H6 H -0.003219 0.365241 0.494253 0.028 Uiso 1 1 calc R U . . .
C7 C 0.1783(2) 0.40973(11) 0.5564(2) 0.0236(5) Uani 1 1 d . . . . .
C8 C 0.2444(2) 0.46077(11) 0.5347(2) 0.0261(5) Uani 1 1 d . . . . .
H8 H 0.336761 0.467898 0.588662 0.031 Uiso 1 1 calc R U . . .
C9 C 0.1740(2) 0.50195(11) 0.4325(2) 0.0254(5) Uani 1 1 d . . . . .
C10 C 0.2487(2) 0.36122(11) 0.6630(2) 0.0271(5) Uani 1 1 d . . . . .
H10A H 0.196034 0.357978 0.709570 0.032 Uiso 1 1 calc R U . . .
H10B H 0.245716 0.318339 0.625558 0.032 Uiso 1 1 calc R U . . .
C11 C 0.3920(2) 0.37512(11) 0.7557(2) 0.0228(5) Uani 1 1 d . . . . .
C12 C 0.4965(2) 0.34532(11) 0.7514(2) 0.0257(5) Uani 1 1 d . . . . .
H12 H 0.479263 0.315386 0.686044 0.031 Uiso 1 1 calc R U . . .
C13 C 0.6518(2) 0.39713(11) 0.9347(2) 0.0223(5) Uani 1 1 d . . . . .
C14 C 0.4271(2) 0.42055(11) 0.8566(2) 0.0219(5) Uani 1 1 d . . . . .
O4 O 0.97297(16) 0.33731(8) 0.99682(15) 0.0288(4) Uani 1 1 d . . . . .
O5 O 0.83315(16) 0.29289(8) 0.81651(15) 0.0306(4) Uani 1 1 d . . . . .
O6 O 1.16459(17) 0.15427(8) 0.72625(15) 0.0320(4) Uani 1 1 d . . . . .
H6A H 1.104977 0.161620 0.653124 0.048 Uiso 1 1 calc R U . . .
O7 O 1.41023(16) 0.20064(9) 0.89189(16) 0.0351(5) Uani 1 1 d . . . . .
H7 H 1.390570 0.175170 0.831772 0.053 Uiso 1 1 calc R U . . .
O8 O 1.43415(16) 0.29746(9) 1.05356(16) 0.0324(4) Uani 1 1 d . . . . .
H8A H 1.493255 0.275727 1.046475 0.049 Uiso 1 1 calc R U . . .
C15 C 0.9507(2) 0.30431(11) 0.9011(2) 0.0243(5) Uani 1 1 d . . . . .
C16 C 1.0696(2) 0.27834(11) 0.8900(2) 0.0226(5) Uani 1 1 d . . . . .
C17 C 1.0553(2) 0.23059(11) 0.8032(2) 0.0237(5) Uani 1 1 d . . . . .
H17 H 0.968668 0.216372 0.744506 0.028 Uiso 1 1 calc R U . . .
C18 C 1.1681(2) 0.20398(11) 0.8030(2) 0.0223(5) Uani 1 1 d . . . . .
C19 C 1.2959(2) 0.22541(11) 0.8871(2) 0.0239(5) Uani 1 1 d . . . . .
C20 C 1.3093(2) 0.27461(11) 0.9708(2) 0.0234(5) Uani 1 1 d . . . . .
C21 C 1.1973(2) 0.30023(11) 0.9734(2) 0.0239(5) Uani 1 1 d . . . . .
H21 H 1.207223 0.332912 1.032308 0.029 Uiso 1 1 calc R U . . .
O9 O 1.67539(18) 0.25641(9) 1.08907(15) 0.0370(5) Uani 1 1 d . . . . .
H9 H 1.721005 0.246511 1.164661 0.055 Uiso 1 1 calc R U . . .
C22 C 1.7261(3) 0.22326(13) 1.0165(2) 0.0323(6) Uani 1 1 d . . . . .
H22A H 1.652718 0.214462 0.933134 0.048 Uiso 1 1 calc R U . . .
H22B H 1.766891 0.182412 1.057369 0.048 Uiso 1 1 calc R U . . .
H22C H 1.793715 0.250115 1.008973 0.048 Uiso 1 1 calc R U . . .
O10 O 1.43911(18) 0.11872(9) 0.73596(15) 0.0334(4) Uani 1 1 d . . . . .
H10 H 1.446372 0.138579 0.678724 0.050 Uiso 1 1 calc R U . . .
C23 C 1.3715(3) 0.05968(14) 0.6891(3) 0.0539(9) Uani 1 1 d . . . . .
H23A H 1.306457 0.064908 0.600953 0.081 Uiso 1 1 calc R U . . .
H23B H 1.324719 0.046978 0.736848 0.081 Uiso 1 1 calc R U . . .
H23C H 1.436448 0.026194 0.696972 0.081 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 1.437(3) . ?
O1 C4 1.388(3) . ?
O2 C2 1.433(3) . ?
O2 C5 1.377(3) . ?
O3 C3 1.420(3) . ?
O3 C9 1.378(3) . ?
N1 H1 0.8800 . ?
N1 C12 1.364(3) . ?
N1 C13 1.357(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C13 1.324(3) . ?
N3 C13 1.337(3) . ?
N3 C14 1.352(3) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N4 C14 1.327(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2C 0.9800 . ?
C2 H2D 0.9800 . ?
C2 H2E 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.393(3) . ?
C4 C9 1.384(3) . ?
C5 C6 1.384(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.393(3) . ?
C7 C8 1.385(3) . ?
C7 C10 1.533(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.405(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.507(3) . ?
C11 C12 1.351(3) . ?
C11 C14 1.443(3) . ?
C12 H12 0.9500 . ?
O4 C15 1.264(3) . ?
O5 C15 1.265(3) . ?
O6 H6A 0.8400 . ?
O6 C18 1.373(3) . ?
O7 H7 0.8400 . ?
O7 C19 1.362(3) . ?
O8 H8A 0.8400 . ?
O8 C20 1.379(3) . ?
C15 C16 1.506(3) . ?
C16 C17 1.395(3) . ?
C16 C21 1.396(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(3) . ?
C18 C19 1.396(3) . ?
C19 C20 1.393(3) . ?
C20 C21 1.382(3) . ?
C21 H21 0.9500 . ?
O9 H9 0.8400 . ?
O9 C22 1.425(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O10 H10 0.8400 . ?
O10 C23 1.413(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C4 O1 C1 114.31(19) . . ?
C5 O2 C2 117.65(18) . . ?
C9 O3 C3 118.27(19) . . ?
C12 N1 H1 120.2 . . ?
C13 N1 H1 120.2 . . ?
C13 N1 C12 119.5(2) . . ?
H2A N2 H2B 120.0 . . ?
C13 N2 H2A 120.0 . . ?
C13 N2 H2B 120.0 . . ?
C13 N3 C14 118.19(19) . . ?
H4A N4 H4B 120.0 . . ?
C14 N4 H4A 120.0 . . ?
C14 N4 H4B 120.0 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 H2C 109.5 . . ?
O2 C2 H2D 109.5 . . ?
O2 C2 H2E 109.5 . . ?
H2C C2 H2D 109.5 . . ?
H2C C2 H2E 109.5 . . ?
H2D C2 H2E 109.5 . . ?
O3 C3 H3A 109.5 . . ?
O3 C3 H3B 109.5 . . ?
O3 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C4 C5 118.1(2) . . ?
C9 C4 O1 122.4(2) . . ?
C9 C4 C5 119.4(2) . . ?
O2 C5 C4 114.52(19) . . ?
O2 C5 C6 124.7(2) . . ?
C6 C5 C4 120.8(2) . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.6(2) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C10 116.7(2) . . ?
C8 C7 C6 120.3(2) . . ?
C8 C7 C10 123.0(2) . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.6(2) . . ?
C9 C8 H8 120.2 . . ?
O3 C9 C4 115.2(2) . . ?
O3 C9 C8 124.6(2) . . ?
C4 C9 C8 120.2(2) . . ?
C7 C10 H10A 108.0 . . ?
C7 C10 H10B 108.0 . . ?
H10A C10 H10B 107.2 . . ?
C11 C10 C7 117.3(2) . . ?
C11 C10 H10A 108.0 . . ?
C11 C10 H10B 108.0 . . ?
C12 C11 C10 122.5(2) . . ?
C12 C11 C14 115.3(2) . . ?
C14 C11 C10 122.2(2) . . ?
N1 C12 H12 118.9 . . ?
C11 C12 N1 122.3(2) . . ?
C11 C12 H12 118.9 . . ?
N2 C13 N1 118.1(2) . . ?
N2 C13 N3 119.7(2) . . ?
N3 C13 N1 122.2(2) . . ?
N3 C14 C11 122.3(2) . . ?
N4 C14 N3 115.9(2) . . ?
N4 C14 C11 121.8(2) . . ?
C18 O6 H6A 109.5 . . ?
C19 O7 H7 109.5 . . ?
C20 O8 H8A 109.5 . . ?
O4 C15 O5 122.0(2) . . ?
O4 C15 C16 117.7(2) . . ?
O5 C15 C16 120.2(2) . . ?
C17 C16 C15 121.4(2) . . ?
C17 C16 C21 119.7(2) . . ?
C21 C16 C15 118.8(2) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.7(2) . . ?
C18 C17 H17 120.1 . . ?
O6 C18 C17 124.0(2) . . ?
O6 C18 C19 115.3(2) . . ?
C17 C18 C19 120.6(2) . . ?
O7 C19 C18 123.2(2) . . ?
O7 C19 C20 117.5(2) . . ?
C20 C19 C18 119.3(2) . . ?
O8 C20 C19 120.6(2) . . ?
O8 C20 C21 119.2(2) . . ?
C21 C20 C19 120.2(2) . . ?
C16 C21 H21 119.8 . . ?
C20 C21 C16 120.4(2) . . ?
C20 C21 H21 119.8 . . ?
C22 O9 H9 109.5 . . ?
O9 C22 H22A 109.5 . . ?
O9 C22 H22B 109.5 . . ?
O9 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 O10 H10 109.5 . . ?
O10 C23 H23A 109.5 . . ?
O10 C23 H23B 109.5 . . ?
O10 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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 C4 C5 O2 4.2(3) . . . . ?
O1 C4 C5 C6 -176.4(2) . . . . ?
O1 C4 C9 O3 0.8(3) . . . . ?
O1 C4 C9 C8 179.0(2) . . . . ?
O2 C5 C6 C7 176.3(2) . . . . ?
C1 O1 C4 C5 -117.7(2) . . . . ?
C1 O1 C4 C9 65.2(3) . . . . ?
C2 O2 C5 C4 -173.3(2) . . . . ?
C2 O2 C5 C6 7.3(3) . . . . ?
C3 O3 C9 C4 -160.8(2) . . . . ?
C3 O3 C9 C8 21.2(4) . . . . ?
C4 C5 C6 C7 -3.1(3) . . . . ?
C5 C4 C9 O3 -176.2(2) . . . . ?
C5 C4 C9 C8 2.0(4) . . . . ?
C5 C6 C7 C8 2.6(3) . . . . ?
C5 C6 C7 C10 -175.3(2) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C6 C7 C10 C11 -175.0(2) . . . . ?
C7 C8 C9 O3 175.5(2) . . . . ?
C7 C8 C9 C4 -2.4(4) . . . . ?
C7 C10 C11 C12 -100.9(3) . . . . ?
C7 C10 C11 C14 80.1(3) . . . . ?
C8 C7 C10 C11 7.2(3) . . . . ?
C9 C4 C5 O2 -178.7(2) . . . . ?
C9 C4 C5 C6 0.8(3) . . . . ?
C10 C7 C8 C9 177.9(2) . . . . ?
C10 C11 C12 N1 -178.1(2) . . . . ?
C10 C11 C14 N3 174.8(2) . . . . ?
C10 C11 C14 N4 -5.8(3) . . . . ?
C12 N1 C13 N2 177.5(2) . . . . ?
C12 N1 C13 N3 -3.9(3) . . . . ?
C12 C11 C14 N3 -4.3(3) . . . . ?
C12 C11 C14 N4 175.2(2) . . . . ?
C13 N1 C12 C11 3.0(3) . . . . ?
C13 N3 C14 N4 -176.0(2) . . . . ?
C13 N3 C14 C11 3.5(3) . . . . ?
C14 N3 C13 N1 0.7(3) . . . . ?
C14 N3 C13 N2 179.2(2) . . . . ?
C14 C11 C12 N1 0.9(3) . . . . ?
O4 C15 C16 C17 166.0(2) . . . . ?
O4 C15 C16 C21 -10.5(3) . . . . ?
O5 C15 C16 C17 -13.9(3) . . . . ?
O5 C15 C16 C21 169.6(2) . . . . ?
O6 C18 C19 O7 1.8(3) . . . . ?
O6 C18 C19 C20 -178.4(2) . . . . ?
O7 C19 C20 O8 0.9(3) . . . . ?
O7 C19 C20 C21 -177.8(2) . . . . ?
O8 C20 C21 C16 179.5(2) . . . . ?
C15 C16 C17 C18 -174.5(2) . . . . ?
C15 C16 C21 C20 176.1(2) . . . . ?
C16 C17 C18 O6 176.1(2) . . . . ?
C16 C17 C18 C19 -1.3(3) . . . . ?
C17 C16 C21 C20 -0.4(3) . . . . ?
C17 C18 C19 O7 179.4(2) . . . . ?
C17 C18 C19 C20 -0.8(4) . . . . ?
C18 C19 C20 O8 -178.9(2) . . . . ?
C18 C19 C20 C21 2.4(4) . . . . ?
C19 C20 C21 C16 -1.8(4) . . . . ?
C21 C16 C17 C18 1.9(3) . . . . ?

_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 1.732
_oxdiff_exptl_absorpt_empirical_full_min 0.690
