# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_hn1109
_database_code_depnum_ccdc_archive 'CCDC 2222382'
loop_
_audit_author_name
_audit_author_address
'Qi-Liang Yang'
;Henan normal university
China
;
_audit_update_record             
;
2022-11-26 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;
_audit_creation_date             2022-11-10
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 N6 O S'
_chemical_formula_sum            'C20 H16 N6 O S'
_chemical_formula_weight         388.45
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   11.3223(3)
_cell_length_b                   15.5202(6)
_cell_length_c                   10.3674(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1821.80(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3571
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.0660
_cell_measurement_theta_min      4.2120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.783
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6353
_diffrn_reflns_point_group_measured_fraction_full 0.921
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.759
_diffrn_reflns_theta_min         4.835
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00  -5.00   1.00    1.00    --  -40.73 -19.00  60.00  114
  2  ω     25.00  97.00   1.00    1.00    --   40.73-125.00 120.00   72
  3  ω     29.00  55.00   1.00    1.00    --   40.73-125.00-180.00   26
  4  ω     75.00 141.00   1.00    1.00    --  107.58  77.00 -90.00   66
  5  ω     37.00 124.00   1.00    1.00    --  107.58 -45.00 -30.00   87
  6  ω    109.00 163.00   1.00    1.00    --  107.58 125.00-120.00   54
  7  ω    101.00 141.00   1.00    1.00    --  107.58 125.00 -90.00   40
  8  ω     79.00 177.00   1.00    1.00    --  107.58  30.00-150.00   98
  9  ω     61.00 116.00   1.00    1.00    --  107.58-125.00 120.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0798309000
_diffrn_orient_matrix_UB_12      -0.0036853000
_diffrn_orient_matrix_UB_13      -0.1203669000
_diffrn_orient_matrix_UB_21      0.0321852000
_diffrn_orient_matrix_UB_22      0.0955638000
_diffrn_orient_matrix_UB_23      0.0186578000
_diffrn_orient_matrix_UB_31      0.1051996000
_diffrn_orient_matrix_UB_32      -0.0265292000
_diffrn_orient_matrix_UB_33      0.0854225000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.831
_reflns_Friedel_fraction_max     0.784
_reflns_number_gt                3184
_reflns_number_total             3278
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1199 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(2)
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3278
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.053
_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)+(0.0505P)²+0.8344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1132
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Others
 Sof(S1B)=Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(1)
 Sof(S1)=Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C12(H12), C15(H15), C16(H16),
 C18(H18), C19(H19)
3.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C20(H20D,H20E,H20F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.12737(10) 0.05287(11) 0.32165(13) 0.0327(5) Uani 0.816(6) 1 d . . P A 1
S1B S 0.1117(6) 0.1091(7) 0.2992(8) 0.051(3) Uani 0.184(6) 1 d . . P A 2
O1 O 0.0380(3) 0.1211(3) 0.3368(5) 0.0711(13) Uani 1 1 d . . . . .
N2 N 0.7636(3) 0.45424(19) 0.8099(3) 0.0308(7) Uani 1 1 d . . . . .
N4 N 0.5996(2) 0.26156(19) 0.6334(3) 0.0246(6) Uani 1 1 d . . . . .
N1 N 0.8687(3) 0.3312(2) 0.8084(3) 0.0318(7) Uani 1 1 d . . . . .
N3 N 0.5845(3) 0.4062(2) 0.6996(3) 0.0316(7) Uani 1 1 d . . . . .
N6 N 0.7451(3) 0.1674(2) 0.6678(3) 0.0315(7) Uani 1 1 d . . . . .
N5 N 0.6548(3) 0.1274(2) 0.6011(3) 0.0317(7) Uani 1 1 d . . . . .
C1 C 0.8977(4) 0.6207(3) 0.7105(4) 0.0356(9) Uani 1 1 d . . . . .
H1 H 0.952017 0.598168 0.771657 0.043 Uiso 1 1 calc R U . . .
C2 C 0.9387(4) 0.6719(3) 0.6102(4) 0.0415(10) Uani 1 1 d . . . . .
H2 H 1.020559 0.684134 0.602521 0.050 Uiso 1 1 calc R U . . .
C3 C 0.8593(4) 0.7048(3) 0.5214(5) 0.0463(11) Uani 1 1 d . . . . .
H3 H 0.887047 0.739312 0.452007 0.056 Uiso 1 1 calc R U . . .
C4 C 0.7403(5) 0.6880(3) 0.5331(5) 0.0472(11) Uani 1 1 d . . . . .
H4 H 0.686271 0.711307 0.472387 0.057 Uiso 1 1 calc R U . . .
C5 C 0.6992(4) 0.6369(3) 0.6336(4) 0.0390(9) Uani 1 1 d . . . . .
H5 H 0.617012 0.625649 0.641748 0.047 Uiso 1 1 calc R U . . .
C6 C 0.7783(3) 0.6020(2) 0.7225(4) 0.0317(8) Uani 1 1 d . . . . .
C7 C 0.7344(3) 0.5459(2) 0.8307(4) 0.0331(8) Uani 1 1 d . . . . .
H7A H 0.770062 0.565480 0.912780 0.040 Uiso 1 1 calc R U . . .
H7B H 0.647633 0.552248 0.838125 0.040 Uiso 1 1 calc R U . . .
C8 C 0.8650(3) 0.4131(3) 0.8448(4) 0.0338(8) Uani 1 1 d . . . . .
H8 H 0.927118 0.440396 0.890798 0.041 Uiso 1 1 calc R U . . .
C9 C 0.6964(3) 0.3945(2) 0.7474(4) 0.0286(8) Uani 1 1 d . . . . .
C10 C 0.7626(3) 0.3201(2) 0.7473(4) 0.0288(8) Uani 1 1 d . . . . .
C11 C 0.7111(3) 0.2473(2) 0.6868(4) 0.0267(7) Uani 1 1 d . . . . .
C12 C 0.5384(3) 0.3391(2) 0.6451(4) 0.0301(8) Uani 1 1 d . . . . .
H12 H 0.460344 0.342751 0.612098 0.036 Uiso 1 1 calc R U . . .
C13 C 0.5690(3) 0.1823(2) 0.5810(4) 0.0264(8) Uani 1 1 d . . . . .
C14 C 0.4601(3) 0.1583(2) 0.5121(4) 0.0261(7) Uani 1 1 d . . . . .
C15 C 0.3940(3) 0.2143(3) 0.4371(4) 0.0331(8) Uani 1 1 d . . . . .
H15 H 0.417438 0.272700 0.427731 0.040 Uiso 1 1 calc R U . . .
C16 C 0.2924(4) 0.1837(3) 0.3754(4) 0.0379(9) Uani 1 1 d . . . . .
H16 H 0.245057 0.221744 0.325614 0.045 Uiso 1 1 calc R U . . .
C17 C 0.2611(3) 0.0972(3) 0.3873(4) 0.0370(9) Uani 1 1 d . . . . .
C18 C 0.3292(4) 0.0410(3) 0.4586(4) 0.0380(9) Uani 1 1 d . . . . .
H18 H 0.308382 -0.018181 0.464176 0.046 Uiso 1 1 calc R U . . .
C19 C 0.4278(4) 0.0715(3) 0.5217(4) 0.0327(8) Uani 1 1 d . . . . .
H19 H 0.474247 0.033240 0.572172 0.039 Uiso 1 1 calc R U . . .
C20 C 0.1682(4) 0.0500(3) 0.1585(5) 0.0531(12) Uani 1 1 d . . . . .
H20A H 0.101073 0.030452 0.106552 0.080 Uiso 0.816(6) 1 calc R U P A 1
H20B H 0.234586 0.010238 0.147190 0.080 Uiso 0.816(6) 1 calc R U P A 1
H20C H 0.191775 0.107882 0.130625 0.080 Uiso 0.816(6) 1 calc R U P A 1
H20D H 0.199048 -0.005960 0.186267 0.080 Uiso 0.184(6) 1 calc R U P A 2
H20E H 0.231607 0.083364 0.117839 0.080 Uiso 0.184(6) 1 calc R U P A 2
H20F H 0.104094 0.041251 0.096382 0.080 Uiso 0.184(6) 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
S1 O1 1.474(4) . ?
S1 C17 1.797(4) . ?
S1 C20 1.754(6) . ?
S1B O1 0.940(8) . ?
S1B C17 1.931(8) . ?
S1B C20 1.838(9) . ?
N2 C7 1.477(5) . ?
N2 C8 1.363(5) . ?
N2 C9 1.364(5) . ?
N4 C11 1.396(4) . ?
N4 C12 1.393(4) . ?
N4 C13 1.388(5) . ?
N1 C8 1.326(5) . ?
N1 C10 1.369(4) . ?
N3 C9 1.373(5) . ?
N3 C12 1.296(5) . ?
N6 N5 1.381(4) . ?
N6 C11 1.315(5) . ?
N5 C13 1.309(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.388(6) . ?
C1 C6 1.388(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(6) . ?
C6 C7 1.504(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8 0.9500 . ?
C9 C10 1.376(5) . ?
C10 C11 1.418(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.473(5) . ?
C14 C15 1.385(6) . ?
C14 C19 1.400(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.399(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.394(6) . ?
C17 C18 1.380(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.377(6) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 H20D 0.9800 . ?
C20 H20E 0.9800 . ?
C20 H20F 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
O1 S1 C17 105.2(2) . . ?
O1 S1 C20 107.6(3) . . ?
C20 S1 C17 98.8(2) . . ?
O1 S1B C17 126.9(7) . . ?
O1 S1B C20 137.5(6) . . ?
C20 S1B C17 91.3(4) . . ?
C8 N2 C7 127.0(3) . . ?
C8 N2 C9 106.1(3) . . ?
C9 N2 C7 126.8(3) . . ?
C12 N4 C11 123.4(3) . . ?
C13 N4 C11 103.9(3) . . ?
C13 N4 C12 132.5(3) . . ?
C8 N1 C10 102.9(3) . . ?
C12 N3 C9 114.9(3) . . ?
C11 N6 N5 106.4(3) . . ?
C13 N5 N6 109.7(3) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C6 C1 C2 120.8(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.5(4) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(4) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(4) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.1(4) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.0(4) . . ?
C1 C6 C7 120.6(4) . . ?
C5 C6 C7 120.3(4) . . ?
N2 C7 C6 112.0(3) . . ?
N2 C7 H7A 109.2 . . ?
N2 C7 H7B 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N2 C8 H8 123.2 . . ?
N1 C8 N2 113.6(3) . . ?
N1 C8 H8 123.2 . . ?
N2 C9 N3 126.6(3) . . ?
N2 C9 C10 105.5(3) . . ?
N3 C9 C10 127.9(3) . . ?
N1 C10 C9 111.9(3) . . ?
N1 C10 C11 131.7(4) . . ?
C9 C10 C11 116.4(3) . . ?
N4 C11 C10 114.9(3) . . ?
N6 C11 N4 110.8(3) . . ?
N6 C11 C10 134.3(3) . . ?
N4 C12 H12 118.9 . . ?
N3 C12 N4 122.2(3) . . ?
N3 C12 H12 118.9 . . ?
N4 C13 C14 128.5(3) . . ?
N5 C13 N4 109.3(3) . . ?
N5 C13 C14 122.3(3) . . ?
C15 C14 C13 124.5(3) . . ?
C15 C14 C19 120.1(4) . . ?
C19 C14 C13 115.3(3) . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.3(4) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.7(4) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 S1 123.4(3) . . ?
C16 C17 S1B 95.1(4) . . ?
C18 C17 S1 115.6(3) . . ?
C18 C17 S1B 143.5(5) . . ?
C18 C17 C16 121.0(4) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 C17 119.4(4) . . ?
C19 C18 H18 120.3 . . ?
C14 C19 H19 119.7 . . ?
C18 C19 C14 120.6(4) . . ?
C18 C19 H19 119.7 . . ?
S1 C20 H20A 109.5 . . ?
S1 C20 H20B 109.5 . . ?
S1 C20 H20C 109.5 . . ?
S1B C20 H20D 109.5 . . ?
S1B C20 H20E 109.5 . . ?
S1B C20 H20F 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H20D C20 H20E 109.5 . . ?
H20D C20 H20F 109.5 . . ?
H20E C20 H20F 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
S1 C17 C18 C19 -174.4(3) . . . . ?
S1B C17 C18 C19 -168.1(6) . . . . ?
O1 S1 C17 C16 -35.9(4) . . . . ?
O1 S1 C17 C18 140.1(4) . . . . ?
N2 C9 C10 N1 0.3(4) . . . . ?
N2 C9 C10 C11 -180.0(3) . . . . ?
N4 C13 C14 C15 31.0(6) . . . . ?
N4 C13 C14 C19 -151.9(4) . . . . ?
N1 C10 C11 N4 -179.5(4) . . . . ?
N1 C10 C11 N6 -0.2(8) . . . . ?
N3 C9 C10 N1 -177.3(3) . . . . ?
N3 C9 C10 C11 2.4(6) . . . . ?
N6 N5 C13 N4 0.3(4) . . . . ?
N6 N5 C13 C14 -179.9(3) . . . . ?
N5 N6 C11 N4 -0.3(4) . . . . ?
N5 N6 C11 C10 -179.6(4) . . . . ?
N5 C13 C14 C15 -148.8(4) . . . . ?
N5 C13 C14 C19 28.3(5) . . . . ?
C1 C2 C3 C4 0.8(7) . . . . ?
C1 C6 C7 N2 -73.9(4) . . . . ?
C2 C1 C6 C5 -1.3(6) . . . . ?
C2 C1 C6 C7 179.5(4) . . . . ?
C2 C3 C4 C5 -0.7(8) . . . . ?
C3 C4 C5 C6 -0.4(7) . . . . ?
C4 C5 C6 C1 1.3(6) . . . . ?
C4 C5 C6 C7 -179.4(4) . . . . ?
C5 C6 C7 N2 106.8(4) . . . . ?
C6 C1 C2 C3 0.2(6) . . . . ?
C7 N2 C8 N1 -177.1(4) . . . . ?
C7 N2 C9 N3 -5.2(6) . . . . ?
C7 N2 C9 C10 177.1(4) . . . . ?
C8 N2 C7 C6 87.3(5) . . . . ?
C8 N2 C9 N3 177.2(4) . . . . ?
C8 N2 C9 C10 -0.5(4) . . . . ?
C8 N1 C10 C9 0.0(4) . . . . ?
C8 N1 C10 C11 -179.7(4) . . . . ?
C9 N2 C7 C6 -89.9(4) . . . . ?
C9 N2 C8 N1 0.5(5) . . . . ?
C9 N3 C12 N4 -1.5(6) . . . . ?
C9 C10 C11 N4 0.8(5) . . . . ?
C9 C10 C11 N6 -179.8(4) . . . . ?
C10 N1 C8 N2 -0.3(4) . . . . ?
C11 N4 C12 N3 4.8(6) . . . . ?
C11 N4 C13 N5 -0.4(4) . . . . ?
C11 N4 C13 C14 179.8(4) . . . . ?
C11 N6 N5 C13 0.0(4) . . . . ?
C12 N4 C11 N6 176.2(3) . . . . ?
C12 N4 C11 C10 -4.2(5) . . . . ?
C12 N4 C13 N5 -175.7(4) . . . . ?
C12 N4 C13 C14 4.5(6) . . . . ?
C12 N3 C9 N2 -179.2(4) . . . . ?
C12 N3 C9 C10 -2.1(6) . . . . ?
C13 N4 C11 N6 0.4(4) . . . . ?
C13 N4 C11 C10 179.9(3) . . . . ?
C13 N4 C12 N3 179.4(4) . . . . ?
C13 C14 C15 C16 179.5(3) . . . . ?
C13 C14 C19 C18 -178.3(4) . . . . ?
C14 C15 C16 C17 -1.8(6) . . . . ?
C15 C14 C19 C18 -1.0(6) . . . . ?
C15 C16 C17 S1 175.5(3) . . . . ?
C15 C16 C17 S1B 173.6(4) . . . . ?
C15 C16 C17 C18 -0.4(6) . . . . ?
C16 C17 C18 C19 1.8(6) . . . . ?
C17 C18 C19 C14 -1.1(6) . . . . ?
C19 C14 C15 C16 2.4(6) . . . . ?
C20 S1 C17 C16 75.1(4) . . . . ?
C20 S1 C17 C18 -108.8(3) . . . . ?

_olex2_date_sample_data_collection 2022-11-09
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.489
_oxdiff_exptl_absorpt_empirical_full_min 0.559
####################################################################### 
# 
# 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_lww-2-20220502
_database_code_depnum_ccdc_archive 'CCDC 2222383'
loop_
_audit_author_name
_audit_author_address
'Qi-Liang Yang'
;Henan normal university
China
;
_audit_update_record             
;
2022-11-26 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;
_audit_creation_date             2022-11-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H13 F3 N6'
_chemical_formula_sum            'C20 H13 F3 N6'
_chemical_formula_weight         394.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 N1 F1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   13.9286(5)
_cell_length_b                   9.9839(4)
_cell_length_c                   13.3315(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.139(3)
_cell_angle_gamma                90
_cell_volume                     1849.07(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4416
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9140
_cell_measurement_theta_min      5.4600
_shelx_estimated_absorpt_T_max   0.835
_shelx_estimated_absorpt_T_min   0.766
_exptl_absorpt_coefficient_mu    0.939
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8232
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.257
_diffrn_reflns_theta_min         5.456
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00  27.00   1.00    1.00    --  -35.62  93.00-179.00   98
  2  ω    101.00 176.00   1.00    3.21    --  107.12  93.00-179.00   75
  3  ω     38.00 109.00   1.00    3.21    --  107.12 -93.00  68.00   71
  4  ω   -103.00 -19.00   1.00    1.00    --  -35.62 -57.00   0.00   84
  5  ω   -108.00 -35.00   1.00    1.00    --  -35.62-178.00-120.00   73
  6  ω     57.00 108.00   1.00    1.00    --   35.62 178.00-120.00   51
  7  ω     57.00 108.00   1.00    1.00    --   35.62 178.00 -30.00   51
  8  ω     57.00 108.00   1.00    1.00    --   35.62 178.00  30.00   51
  9  ω     -6.00  71.00   1.00    1.00    --   35.62 -93.00  68.00   77
 10  ω     40.00 125.00   1.00    3.21    --  107.12 -61.00  90.00   85
 11  ω     40.00 125.00   1.00    3.21    --  107.12 -61.00-150.00   85
 12  ω     39.00 115.00   1.00    3.21    --  107.12 -45.00  60.00   76
 13  ω     80.00 170.00   1.00    3.21    --  107.12  77.00-150.00   90
 14  ω     44.00  75.00   1.00    3.21    --  107.12 -95.00   0.00   31
 15  ω    119.00 166.00   1.00    3.21    --  107.12  61.00  30.00   47
 16  ω    137.00 172.00   1.00    3.21    --  107.12  61.00 120.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0870250000
_diffrn_orient_matrix_UB_12      -0.0818550000
_diffrn_orient_matrix_UB_13      0.0306261000
_diffrn_orient_matrix_UB_21      -0.0675728000
_diffrn_orient_matrix_UB_22      0.1164610000
_diffrn_orient_matrix_UB_23      -0.0333534000
_diffrn_orient_matrix_UB_31      -0.0123743000
_diffrn_orient_matrix_UB_32      -0.0599025000
_diffrn_orient_matrix_UB_33      -0.1065325000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2707
_reflns_number_total             3433
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.298
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0832
_refine_ls_restrained_S_all      1.071
_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)+(0.1472P)²+0.9061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2351
_refine_ls_wR_factor_ref         0.2638
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00N(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00H(H00H), C00K(H00K), C00L(H00L), C00M(H00M),
 C00O(H00O), C00P(H00P), C00R(H00R), C00S(H00S), C00T(H00T)
;
_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
N001 N 0.42663(17) 0.3697(2) 0.31898(18) 0.0505(6) Uani 1 1 d . . . . .
N002 N 0.60819(18) 0.2528(3) 0.54255(19) 0.0557(7) Uani 1 1 d . . . . .
N003 N 0.64717(19) 0.4517(3) 0.47756(19) 0.0584(7) Uani 1 1 d . . . . .
N004 N 0.46058(17) 0.2037(3) 0.44157(19) 0.0546(6) Uani 1 1 d . . . . .
N005 N 0.49842(18) 0.5643(3) 0.2941(2) 0.0594(7) Uani 1 1 d . . . . .
N006 N 0.41729(19) 0.5523(3) 0.2277(2) 0.0602(7) Uani 1 1 d . . . . .
F007 F -0.0208(2) 0.3210(3) -0.0124(3) 0.1415(15) Uani 1 1 d . . . . .
C008 C 0.5384(2) 0.2831(3) 0.4682(2) 0.0502(7) Uani 1 1 d . . . . .
C009 C 0.5026(2) 0.4545(3) 0.3488(2) 0.0499(7) Uani 1 1 d . . . . .
C00A C 0.5645(2) 0.4033(3) 0.4290(2) 0.0488(6) Uani 1 1 d . . . . .
C00B C 0.3756(2) 0.4378(3) 0.2423(2) 0.0533(7) Uani 1 1 d . . . . .
C00C C 0.4070(2) 0.2505(3) 0.3671(2) 0.0550(7) Uani 1 1 d . . . . .
H00C H 0.352612 0.202180 0.344422 0.066 Uiso 1 1 calc R U . . .
C00D C 0.2887(2) 0.3846(3) 0.1868(2) 0.0552(7) Uani 1 1 d . . . . .
C00E C 0.6703(2) 0.3583(3) 0.5451(2) 0.0604(8) Uani 1 1 d . . . . .
H00E H 0.724106 0.363949 0.590438 0.073 Uiso 1 1 calc R U . . .
F00F F -0.0191(3) 0.1672(4) 0.0914(4) 0.174(2) Uani 1 1 d . . . . .
C00G C 0.7020(2) 0.1064(3) 0.6620(2) 0.0602(8) Uani 1 1 d . . . . .
C00H C 0.2898(2) 0.2594(3) 0.1415(3) 0.0642(8) Uani 1 1 d . . . . .
H00H H 0.346042 0.208802 0.145831 0.077 Uiso 1 1 calc R U . . .
F00I F 0.0519(3) 0.1430(5) -0.0375(5) 0.198(2) Uani 1 1 d . . . . .
C00J C 0.1249(3) 0.2847(4) 0.0836(3) 0.0733(10) Uani 1 1 d . . . . .
C00K C 0.7315(3) 0.1636(4) 0.7538(3) 0.0726(9) Uani 1 1 d . . . . .
H00K H 0.690777 0.221779 0.784924 0.087 Uiso 1 1 calc R U . . .
C00L C 0.2081(3) 0.2099(3) 0.0903(3) 0.0710(9) Uani 1 1 d . . . . .
H00L H 0.209123 0.125906 0.060227 0.085 Uiso 1 1 calc R U . . .
C00M C 0.2051(3) 0.4605(3) 0.1777(3) 0.0722(10) Uani 1 1 d . . . . .
H00M H 0.204040 0.545486 0.206182 0.087 Uiso 1 1 calc R U . . .
C00N C 0.6045(3) 0.1407(4) 0.6141(3) 0.0732(10) Uani 1 1 d . . . . .
H00A H 0.577589 0.062610 0.579060 0.088 Uiso 1 1 calc R U . . .
H00B H 0.562261 0.164345 0.666114 0.088 Uiso 1 1 calc R U . . .
C00O C 0.1238(3) 0.4102(4) 0.1265(4) 0.0815(12) Uani 1 1 d . . . . .
H00O H 0.067798 0.461154 0.120799 0.098 Uiso 1 1 calc R U . . .
C00P C 0.7626(3) 0.0200(4) 0.6173(4) 0.0856(12) Uani 1 1 d . . . . .
H00P H 0.744003 -0.018203 0.555274 0.103 Uiso 1 1 calc R U . . .
C00Q C 0.0359(4) 0.2295(5) 0.0300(5) 0.1032(17) Uani 1 1 d . . . . .
C00R C 0.8208(4) 0.1347(6) 0.7989(3) 0.0941(14) Uani 1 1 d . . . . .
H00R H 0.840544 0.174390 0.859997 0.113 Uiso 1 1 calc R U . . .
C00S C 0.8807(4) 0.0483(7) 0.7548(5) 0.1139(19) Uani 1 1 d . . . . .
H00S H 0.941113 0.028952 0.785768 0.137 Uiso 1 1 calc R U . . .
C00T C 0.8517(4) -0.0098(6) 0.6650(5) 0.1087(17) Uani 1 1 d . . . . .
H00T H 0.892102 -0.070017 0.635559 0.130 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
N001 C009 1.391(4) . ?
N001 C00B 1.381(4) . ?
N001 C00C 1.389(4) . ?
N002 C008 1.371(4) . ?
N002 C00E 1.361(4) . ?
N002 C00N 1.475(4) . ?
N003 C00A 1.368(4) . ?
N003 C00E 1.321(4) . ?
N004 C008 1.369(4) . ?
N004 C00C 1.286(4) . ?
N005 N006 1.390(4) . ?
N005 C009 1.316(4) . ?
N006 C00B 1.303(4) . ?
F007 C00Q 1.309(5) . ?
C008 C00A 1.368(4) . ?
C009 C00A 1.419(4) . ?
C00B C00D 1.472(4) . ?
C00C H00C 0.9300 . ?
C00D C00H 1.389(5) . ?
C00D C00M 1.388(4) . ?
C00E H00E 0.9300 . ?
F00F C00Q 1.317(7) . ?
C00G C00K 1.386(5) . ?
C00G C00N 1.498(5) . ?
C00G C00P 1.374(5) . ?
C00H H00H 0.9300 . ?
C00H C00L 1.376(5) . ?
F00I C00Q 1.278(7) . ?
C00J C00L 1.377(5) . ?
C00J C00O 1.378(5) . ?
C00J C00Q 1.491(5) . ?
C00K H00K 0.9300 . ?
C00K C00R 1.372(6) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00O 1.373(5) . ?
C00N H00A 0.9700 . ?
C00N H00B 0.9700 . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00P C00T 1.385(7) . ?
C00R H00R 0.9300 . ?
C00R C00S 1.363(8) . ?
C00S H00S 0.9300 . ?
C00S C00T 1.365(8) . ?
C00T H00T 0.9300 . ?

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
C00B N001 C009 104.6(2) . . ?
C00B N001 C00C 131.0(3) . . ?
C00C N001 C009 124.1(3) . . ?
C008 N002 C00N 125.4(3) . . ?
C00E N002 C008 105.3(3) . . ?
C00E N002 C00N 128.5(3) . . ?
C00E N003 C00A 103.2(2) . . ?
C00C N004 C008 113.2(3) . . ?
C009 N005 N006 106.4(2) . . ?
C00B N006 N005 109.3(3) . . ?
N004 C008 N002 124.5(3) . . ?
C00A C008 N002 106.0(3) . . ?
C00A C008 N004 129.5(3) . . ?
N001 C009 C00A 113.9(2) . . ?
N005 C009 N001 110.2(3) . . ?
N005 C009 C00A 135.9(3) . . ?
N003 C00A C009 132.4(3) . . ?
C008 C00A N003 111.5(3) . . ?
C008 C00A C009 116.1(3) . . ?
N001 C00B C00D 123.7(3) . . ?
N006 C00B N001 109.4(3) . . ?
N006 C00B C00D 126.9(3) . . ?
N001 C00C H00C 118.5 . . ?
N004 C00C N001 123.0(3) . . ?
N004 C00C H00C 118.5 . . ?
C00H C00D C00B 120.5(3) . . ?
C00M C00D C00B 120.1(3) . . ?
C00M C00D C00H 119.3(3) . . ?
N002 C00E H00E 123.0 . . ?
N003 C00E N002 114.0(3) . . ?
N003 C00E H00E 123.0 . . ?
C00K C00G C00N 119.0(3) . . ?
C00P C00G C00K 119.3(4) . . ?
C00P C00G C00N 121.7(4) . . ?
C00D C00H H00H 119.9 . . ?
C00L C00H C00D 120.3(3) . . ?
C00L C00H H00H 119.9 . . ?
C00L C00J C00O 120.0(3) . . ?
C00L C00J C00Q 119.8(4) . . ?
C00O C00J C00Q 120.1(4) . . ?
C00G C00K H00K 119.9 . . ?
C00R C00K C00G 120.1(4) . . ?
C00R C00K H00K 119.9 . . ?
C00H C00L C00J 120.0(3) . . ?
C00H C00L H00L 120.0 . . ?
C00J C00L H00L 120.0 . . ?
C00D C00M H00M 120.0 . . ?
C00O C00M C00D 120.0(3) . . ?
C00O C00M H00M 120.0 . . ?
N002 C00N C00G 112.1(3) . . ?
N002 C00N H00A 109.2 . . ?
N002 C00N H00B 109.2 . . ?
C00G C00N H00A 109.2 . . ?
C00G C00N H00B 109.2 . . ?
H00A C00N H00B 107.9 . . ?
C00J C00O H00O 119.8 . . ?
C00M C00O C00J 120.4(3) . . ?
C00M C00O H00O 119.8 . . ?
C00G C00P H00P 120.2 . . ?
C00G C00P C00T 119.6(5) . . ?
C00T C00P H00P 120.2 . . ?
F007 C00Q F00F 103.8(5) . . ?
F007 C00Q C00J 113.8(4) . . ?
F00F C00Q C00J 112.2(5) . . ?
F00I C00Q F007 107.3(5) . . ?
F00I C00Q F00F 105.0(5) . . ?
F00I C00Q C00J 114.0(5) . . ?
C00K C00R H00R 119.7 . . ?
C00S C00R C00K 120.6(5) . . ?
C00S C00R H00R 119.7 . . ?
C00R C00S H00S 120.2 . . ?
C00R C00S C00T 119.6(5) . . ?
C00T C00S H00S 120.2 . . ?
C00P C00T H00T 119.6 . . ?
C00S C00T C00P 120.7(5) . . ?
C00S C00T H00T 119.6 . . ?

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
N001 C009 C00A N003 177.7(3) . . . . ?
N001 C009 C00A C008 -3.0(4) . . . . ?
N001 C00B C00D C00H -53.7(4) . . . . ?
N001 C00B C00D C00M 127.6(3) . . . . ?
N002 C008 C00A N003 -1.4(3) . . . . ?
N002 C008 C00A C009 179.2(2) . . . . ?
N004 C008 C00A N003 179.2(3) . . . . ?
N004 C008 C00A C009 -0.2(4) . . . . ?
N005 N006 C00B N001 0.4(3) . . . . ?
N005 N006 C00B C00D -178.9(3) . . . . ?
N005 C009 C00A N003 -2.4(6) . . . . ?
N005 C009 C00A C008 176.9(3) . . . . ?
N006 N005 C009 N001 0.8(3) . . . . ?
N006 N005 C009 C00A -179.2(3) . . . . ?
N006 C00B C00D C00H 125.5(4) . . . . ?
N006 C00B C00D C00M -53.2(5) . . . . ?
C008 N002 C00E N003 -1.3(4) . . . . ?
C008 N002 C00N C00G 161.0(3) . . . . ?
C008 N004 C00C N001 -0.1(4) . . . . ?
C009 N001 C00B N006 0.1(3) . . . . ?
C009 N001 C00B C00D 179.4(3) . . . . ?
C009 N001 C00C N004 -3.5(5) . . . . ?
C009 N005 N006 C00B -0.7(3) . . . . ?
C00A N003 C00E N002 0.5(4) . . . . ?
C00B N001 C009 N005 -0.5(3) . . . . ?
C00B N001 C009 C00A 179.4(2) . . . . ?
C00B N001 C00C N004 -176.4(3) . . . . ?
C00B C00D C00H C00L 179.6(3) . . . . ?
C00B C00D C00M C00O -179.5(4) . . . . ?
C00C N001 C009 N005 -175.0(3) . . . . ?
C00C N001 C009 C00A 4.9(4) . . . . ?
C00C N001 C00B N006 174.0(3) . . . . ?
C00C N001 C00B C00D -6.7(5) . . . . ?
C00C N004 C008 N002 -177.4(3) . . . . ?
C00C N004 C008 C00A 1.9(5) . . . . ?
C00D C00H C00L C00J 0.2(6) . . . . ?
C00D C00M C00O C00J -0.3(7) . . . . ?
C00E N002 C008 N004 -179.0(3) . . . . ?
C00E N002 C008 C00A 1.5(3) . . . . ?
C00E N002 C00N C00G -30.7(5) . . . . ?
C00E N003 C00A C008 0.6(3) . . . . ?
C00E N003 C00A C009 179.9(3) . . . . ?
C00G C00K C00R C00S -0.9(7) . . . . ?
C00G C00P C00T C00S -1.6(8) . . . . ?
C00H C00D C00M C00O 1.7(6) . . . . ?
C00K C00G C00N N002 93.8(4) . . . . ?
C00K C00G C00P C00T 0.8(6) . . . . ?
C00K C00R C00S C00T 0.1(8) . . . . ?
C00L C00J C00O C00M -1.2(7) . . . . ?
C00L C00J C00Q F007 -149.6(5) . . . . ?
C00L C00J C00Q F00F 92.9(6) . . . . ?
C00L C00J C00Q F00I -26.1(8) . . . . ?
C00M C00D C00H C00L -1.7(5) . . . . ?
C00N N002 C008 N004 -8.5(5) . . . . ?
C00N N002 C008 C00A 172.0(3) . . . . ?
C00N N002 C00E N003 -171.4(3) . . . . ?
C00N C00G C00K C00R -179.5(3) . . . . ?
C00N C00G C00P C00T -179.3(4) . . . . ?
C00O C00J C00L C00H 1.3(6) . . . . ?
C00O C00J C00Q F007 30.5(8) . . . . ?
C00O C00J C00Q F00F -87.0(6) . . . . ?
C00O C00J C00Q F00I 154.0(5) . . . . ?
C00P C00G C00K C00R 0.4(6) . . . . ?
C00P C00G C00N N002 -86.1(4) . . . . ?
C00Q C00J C00L C00H -178.6(4) . . . . ?
C00Q C00J C00O C00M 178.7(5) . . . . ?
C00R C00S C00T C00P 1.2(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.169
_oxdiff_exptl_absorpt_empirical_full_min 0.444
####################################################################### 
# 
# 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_lww-4-20220511
_database_code_depnum_ccdc_archive 'CCDC 2222384'
loop_
_audit_author_name
_audit_author_address
'Qi-Liang Yang'
;Henan normal university
China
;
_audit_update_record             
;
2022-11-26 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;
_audit_creation_date             2022-11-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 N6 O4'
_chemical_formula_sum            'C20 H20 N6 O4'
_chemical_formula_weight         408.42
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.58890(10)
_cell_length_b                   13.3226(2)
_cell_length_c                   17.0548(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1951.52(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3946
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.4180
_cell_measurement_theta_min      5.7660
_shelx_estimated_absorpt_T_max   0.851
_shelx_estimated_absorpt_T_min   0.788
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5868
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.514
_diffrn_reflns_theta_min         4.211
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -96.00 -10.00   1.00    1.00    --  -35.62 139.00 -87.00   86
  2  ω    -70.00 -40.00   1.00    1.00    --  -35.62  90.00-150.00   30
  3  ω     51.00 114.00   1.00    1.51    --  107.12 -32.00-111.00   63
  4  ω    108.00 165.00   1.00    1.51    --  107.12  90.00-150.00   57
  5  ω     47.00 111.00   1.00    1.51    --  107.12-131.00  26.00   64
  6  ω     72.00 101.00   1.00    1.51    --  107.12-139.00-148.00   29
  7  ω     19.00  71.00   1.00    1.00    --   35.62  57.00-150.00   52
  8  ω     22.00 100.00   1.00    1.00    --   35.62  57.00 -90.00   78
  9  ω     58.00  91.00   1.00    1.51    --  107.12 -95.00-150.00   33
 10  ω     89.00 130.00   1.00    1.51    --  107.12  61.00  30.00   41
 11  ω     39.00 109.00   1.00    1.51    --  107.12 -95.00  30.00   70
 12  ω    129.00 164.00   1.00    1.51    --  107.12 111.00  30.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1450766000
_diffrn_orient_matrix_UB_12      -0.0408397000
_diffrn_orient_matrix_UB_13      -0.0424635000
_diffrn_orient_matrix_UB_21      -0.0750606000
_diffrn_orient_matrix_UB_22      0.0252134000
_diffrn_orient_matrix_UB_23      -0.0797211000
_diffrn_orient_matrix_UB_31      0.0741808000
_diffrn_orient_matrix_UB_32      0.1051386000
_diffrn_orient_matrix_UB_33      0.0025380000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.654
_reflns_Friedel_fraction_full    0.904
_reflns_Friedel_fraction_max     0.858
_reflns_number_gt                3352
_reflns_number_total             3534
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.146
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 1258 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(11)
_refine_ls_extinction_coef       0.0039(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   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3534
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.071
_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)+(0.0397P)²+0.2315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0875
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00E(H00E), C00G(H00G), C00L(H00L), C00M(H00M)
2.b Secondary CH2 refined with riding coordinates:
 C00P(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00K(H00K), C00N(H00N), C00O(H00O), C00Q(H00Q), C00R(H00R),
 C00T(H00T)
2.d Idealised Me refined as rotating group:
 C00S(H00C,H00D,H00F), C00U(H00H,H00I,H00P)
2.e Idealised tetrahedral OH refined as rotating group:
 O005(H005)
;
_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
O001 O 0.8302(2) 0.93479(12) 0.58060(11) 0.0493(5) Uani 1 1 d . . . . .
O002 O 0.9021(2) 0.71047(13) 0.56365(10) 0.0490(4) Uani 1 1 d . . . . .
N003 N 0.4692(2) 0.39753(14) 0.65075(12) 0.0376(4) Uani 1 1 d . . . . .
O004 O 0.6830(2) 0.87079(13) 0.67896(12) 0.0585(5) Uani 1 1 d . . . . .
O005 O 1.1489(2) 0.72239(17) 0.67765(12) 0.0615(5) Uani 1 1 d . . . . .
H005 H 1.219084 0.745488 0.704805 0.092 Uiso 1 1 calc R U . . .
N006 N 0.7705(2) 0.62256(14) 0.66217(12) 0.0424(5) Uani 1 1 d . . . . .
N007 N 0.6081(2) 0.29572(14) 0.72641(14) 0.0460(5) Uani 1 1 d . . . . .
N008 N 0.5297(2) 0.55972(15) 0.60552(12) 0.0442(5) Uani 1 1 d . . . . .
N009 N 0.8374(3) 0.49148(15) 0.73736(15) 0.0526(6) Uani 1 1 d . . . . .
N00A N 0.4778(3) 0.24471(14) 0.70021(14) 0.0457(5) Uani 1 1 d . . . . .
C00B C 0.6997(3) 0.47202(16) 0.69947(15) 0.0404(5) Uani 1 1 d . . . . .
C00C C 0.6021(3) 0.38649(17) 0.69690(14) 0.0386(5) Uani 1 1 d . . . . .
C00D C 0.6565(3) 0.55202(16) 0.65312(14) 0.0386(5) Uani 1 1 d . . . . .
C00E C 0.8157(3) 0.80874(16) 0.67132(13) 0.0397(5) Uani 1 1 d . . . . .
H00E H 0.858389 0.789337 0.722421 0.048 Uiso 1 1 calc R U . . .
C00F C 0.3950(3) 0.30503(17) 0.65610(14) 0.0410(5) Uani 1 1 d . . . . .
C00G C 0.9314(3) 0.86889(17) 0.62345(15) 0.0415(5) Uani 1 1 d . . . . .
H00G H 1.006093 0.905361 0.656262 0.050 Uiso 1 1 calc R U . . .
C00H C 0.2447(3) 0.27859(19) 0.62121(14) 0.0442(6) Uani 1 1 d . . . . .
C00I C 0.7023(3) 0.95716(18) 0.63098(16) 0.0467(6) Uani 1 1 d . . . . .
C00J C 0.4399(3) 0.48238(18) 0.60599(15) 0.0435(6) Uani 1 1 d . . . . .
H00J H 0.351074 0.483435 0.574818 0.052 Uiso 1 1 calc R U . . .
C00K C 0.8750(3) 0.58207(18) 0.71326(19) 0.0530(7) Uani 1 1 d . . . . .
H00K H 0.964450 0.615354 0.729583 0.064 Uiso 1 1 calc R U . . .
C00L C 1.0093(3) 0.79394(19) 0.56983(14) 0.0454(6) Uani 1 1 d . . . . .
H00L H 1.023153 0.824266 0.517947 0.055 Uiso 1 1 calc R U . . .
C00M C 0.7821(3) 0.71764(16) 0.61971(14) 0.0401(5) Uani 1 1 d . . . . .
H00M H 0.683701 0.729200 0.592089 0.048 Uiso 1 1 calc R U . . .
C00N C 0.2213(4) 0.1798(2) 0.59690(18) 0.0615(8) Uani 1 1 d . . . . .
H00N H 0.301695 0.133393 0.601225 0.074 Uiso 1 1 calc R U . . .
C00O C 0.1238(3) 0.3464(2) 0.61452(17) 0.0553(7) Uani 1 1 d . . . . .
H00O H 0.137096 0.412350 0.631086 0.066 Uiso 1 1 calc R U . . .
C00P C 1.1647(3) 0.7581(2) 0.59961(18) 0.0581(7) Uani 1 1 d . . . . .
H00A H 1.203364 0.704741 0.566194 0.070 Uiso 1 1 calc R U . . .
H00B H 1.239103 0.812899 0.598260 0.070 Uiso 1 1 calc R U . . .
C00Q C -0.0171(4) 0.3161(3) 0.5831(2) 0.0730(9) Uani 1 1 d . . . . .
H00Q H -0.098302 0.361900 0.578486 0.088 Uiso 1 1 calc R U . . .
C00R C -0.0375(5) 0.2189(3) 0.5588(2) 0.0833(12) Uani 1 1 d . . . . .
H00R H -0.131948 0.199206 0.536998 0.100 Uiso 1 1 calc R U . . .
C00S C 0.7364(4) 1.0448(2) 0.6847(2) 0.0729(10) Uani 1 1 d . . . . .
H00C H 0.826200 1.029839 0.716058 0.109 Uiso 1 1 calc R U . . .
H00D H 0.648457 1.056453 0.718197 0.109 Uiso 1 1 calc R U . . .
H00F H 0.756131 1.103682 0.653795 0.109 Uiso 1 1 calc R U . . .
C00T C 0.0804(5) 0.1509(3) 0.5666(2) 0.0802(12) Uani 1 1 d . . . . .
H00T H 0.065135 0.084620 0.551357 0.096 Uiso 1 1 calc R U . . .
C00U C 0.5594(4) 0.9714(3) 0.5819(2) 0.0826(11) Uani 1 1 d . . . . .
H00H H 0.571089 1.030519 0.550242 0.124 Uiso 1 1 calc R U . . .
H00I H 0.470385 0.978931 0.615459 0.124 Uiso 1 1 calc R U . . .
H00P H 0.545198 0.914056 0.548664 0.124 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
O001 C00G 1.436(3) . ?
O001 C00I 1.427(3) . ?
O002 C00L 1.448(3) . ?
O002 C00M 1.409(3) . ?
N003 C00C 1.394(3) . ?
N003 C00F 1.390(3) . ?
N003 C00J 1.387(3) . ?
O004 C00E 1.415(3) . ?
O004 C00I 1.422(3) . ?
O005 H005 0.8200 . ?
O005 C00P 1.420(3) . ?
N006 C00D 1.366(3) . ?
N006 C00K 1.362(3) . ?
N006 C00M 1.462(3) . ?
N007 N00A 1.384(3) . ?
N007 C00C 1.311(3) . ?
N008 C00D 1.362(3) . ?
N008 C00J 1.287(3) . ?
N009 C00B 1.372(3) . ?
N009 C00K 1.315(3) . ?
N00A C00F 1.310(3) . ?
C00B C00C 1.415(3) . ?
C00B C00D 1.378(3) . ?
C00E H00E 0.9800 . ?
C00E C00G 1.515(3) . ?
C00E C00M 1.527(3) . ?
C00F C00H 1.465(3) . ?
C00G H00G 0.9800 . ?
C00G C00L 1.510(3) . ?
C00H C00N 1.394(4) . ?
C00H C00O 1.381(4) . ?
C00I C00S 1.512(4) . ?
C00I C00U 1.497(4) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9800 . ?
C00L C00P 1.506(4) . ?
C00M H00M 0.9800 . ?
C00N H00N 0.9300 . ?
C00N C00T 1.371(5) . ?
C00O H00O 0.9300 . ?
C00O C00Q 1.383(4) . ?
C00P H00A 0.9700 . ?
C00P H00B 0.9700 . ?
C00Q H00Q 0.9300 . ?
C00Q C00R 1.371(6) . ?
C00R H00R 0.9300 . ?
C00R C00T 1.366(6) . ?
C00S H00C 0.9600 . ?
C00S H00D 0.9600 . ?
C00S H00F 0.9600 . ?
C00T H00T 0.9300 . ?
C00U H00H 0.9600 . ?
C00U H00I 0.9600 . ?
C00U H00P 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00I O001 C00G 106.72(18) . . ?
C00M O002 C00L 111.33(17) . . ?
C00F N003 C00C 104.16(19) . . ?
C00J N003 C00C 123.0(2) . . ?
C00J N003 C00F 132.5(2) . . ?
C00E O004 C00I 109.03(19) . . ?
C00P O005 H005 109.5 . . ?
C00D N006 C00M 126.07(19) . . ?
C00K N006 C00D 105.78(19) . . ?
C00K N006 C00M 128.0(2) . . ?
C00C N007 N00A 107.3(2) . . ?
C00J N008 C00D 114.5(2) . . ?
C00K N009 C00B 103.8(2) . . ?
C00F N00A N007 108.84(19) . . ?
N009 C00B C00C 132.6(2) . . ?
N009 C00B C00D 110.9(2) . . ?
C00D C00B C00C 116.4(2) . . ?
N003 C00C C00B 114.7(2) . . ?
N007 C00C N003 110.3(2) . . ?
N007 C00C C00B 135.0(2) . . ?
N006 C00D C00B 105.9(2) . . ?
N008 C00D N006 126.1(2) . . ?
N008 C00D C00B 128.0(2) . . ?
O004 C00E H00E 111.9 . . ?
O004 C00E C00G 105.62(18) . . ?
O004 C00E C00M 111.4(2) . . ?
C00G C00E H00E 111.9 . . ?
C00G C00E C00M 103.52(19) . . ?
C00M C00E H00E 111.9 . . ?
N003 C00F C00H 126.2(2) . . ?
N00A C00F N003 109.4(2) . . ?
N00A C00F C00H 124.3(2) . . ?
O001 C00G C00E 101.6(2) . . ?
O001 C00G H00G 112.6 . . ?
O001 C00G C00L 111.4(2) . . ?
C00E C00G H00G 112.6 . . ?
C00L C00G C00E 105.50(19) . . ?
C00L C00G H00G 112.6 . . ?
C00N C00H C00F 118.3(3) . . ?
C00O C00H C00F 122.6(2) . . ?
C00O C00H C00N 119.0(3) . . ?
O001 C00I C00S 112.1(2) . . ?
O001 C00I C00U 108.7(2) . . ?
O004 C00I O001 105.51(19) . . ?
O004 C00I C00S 107.4(2) . . ?
O004 C00I C00U 109.2(3) . . ?
C00U C00I C00S 113.5(3) . . ?
N003 C00J H00J 118.4 . . ?
N008 C00J N003 123.2(2) . . ?
N008 C00J H00J 118.4 . . ?
N006 C00K H00K 123.2 . . ?
N009 C00K N006 113.7(2) . . ?
N009 C00K H00K 123.2 . . ?
O002 C00L C00G 105.7(2) . . ?
O002 C00L H00L 109.1 . . ?
O002 C00L C00P 110.2(2) . . ?
C00G C00L H00L 109.1 . . ?
C00P C00L C00G 113.5(2) . . ?
C00P C00L H00L 109.1 . . ?
O002 C00M N006 109.09(19) . . ?
O002 C00M C00E 107.86(19) . . ?
O002 C00M H00M 108.4 . . ?
N006 C00M C00E 114.58(19) . . ?
N006 C00M H00M 108.4 . . ?
C00E C00M H00M 108.4 . . ?
C00H C00N H00N 119.9 . . ?
C00T C00N C00H 120.3(3) . . ?
C00T C00N H00N 119.9 . . ?
C00H C00O H00O 120.0 . . ?
C00H C00O C00Q 119.9(3) . . ?
C00Q C00O H00O 120.0 . . ?
O005 C00P C00L 109.7(2) . . ?
O005 C00P H00A 109.7 . . ?
O005 C00P H00B 109.7 . . ?
C00L C00P H00A 109.7 . . ?
C00L C00P H00B 109.7 . . ?
H00A C00P H00B 108.2 . . ?
C00O C00Q H00Q 119.9 . . ?
C00R C00Q C00O 120.3(4) . . ?
C00R C00Q H00Q 119.9 . . ?
C00Q C00R H00R 119.9 . . ?
C00T C00R C00Q 120.1(3) . . ?
C00T C00R H00R 119.9 . . ?
C00I C00S H00C 109.5 . . ?
C00I C00S H00D 109.5 . . ?
C00I C00S H00F 109.5 . . ?
H00C C00S H00D 109.5 . . ?
H00C C00S H00F 109.5 . . ?
H00D C00S H00F 109.5 . . ?
C00N C00T H00T 119.8 . . ?
C00R C00T C00N 120.3(3) . . ?
C00R C00T H00T 119.8 . . ?
C00I C00U H00H 109.5 . . ?
C00I C00U H00I 109.5 . . ?
C00I C00U H00P 109.5 . . ?
H00H C00U H00I 109.5 . . ?
H00H C00U H00P 109.5 . . ?
H00I C00U H00P 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
O001 C00G C00L O002 -86.7(2) . . . . ?
O001 C00G C00L C00P 152.4(2) . . . . ?
O002 C00L C00P O005 -65.5(3) . . . . ?
N003 C00F C00H C00N 148.1(3) . . . . ?
N003 C00F C00H C00O -34.6(4) . . . . ?
O004 C00E C00G O001 -25.3(2) . . . . ?
O004 C00E C00G C00L -141.6(2) . . . . ?
O004 C00E C00M O002 130.86(19) . . . . ?
O004 C00E C00M N006 -107.4(2) . . . . ?
N007 N00A C00F N003 0.9(3) . . . . ?
N007 N00A C00F C00H -176.8(2) . . . . ?
N009 C00B C00C N003 179.7(3) . . . . ?
N009 C00B C00C N007 -2.6(5) . . . . ?
N009 C00B C00D N006 0.3(3) . . . . ?
N009 C00B C00D N008 178.3(2) . . . . ?
N00A N007 C00C N003 -0.2(3) . . . . ?
N00A N007 C00C C00B -177.9(3) . . . . ?
N00A C00F C00H C00N -34.7(4) . . . . ?
N00A C00F C00H C00O 142.6(3) . . . . ?
C00B N009 C00K N006 0.0(3) . . . . ?
C00C N003 C00F N00A -0.9(3) . . . . ?
C00C N003 C00F C00H 176.7(2) . . . . ?
C00C N003 C00J N008 -2.8(4) . . . . ?
C00C N007 N00A C00F -0.4(3) . . . . ?
C00C C00B C00D N006 -177.1(2) . . . . ?
C00C C00B C00D N008 0.9(4) . . . . ?
C00D N006 C00K N009 0.2(3) . . . . ?
C00D N006 C00M O002 -105.8(3) . . . . ?
C00D N006 C00M C00E 133.1(2) . . . . ?
C00D N008 C00J N003 -0.3(4) . . . . ?
C00D C00B C00C N003 -3.6(3) . . . . ?
C00D C00B C00C N007 174.0(3) . . . . ?
C00E O004 C00I O001 13.5(3) . . . . ?
C00E O004 C00I C00S -106.3(3) . . . . ?
C00E O004 C00I C00U 130.2(3) . . . . ?
C00E C00G C00L O002 22.7(3) . . . . ?
C00E C00G C00L C00P -98.2(2) . . . . ?
C00F N003 C00C N007 0.7(3) . . . . ?
C00F N003 C00C C00B 178.9(2) . . . . ?
C00F N003 C00J N008 -175.2(2) . . . . ?
C00F C00H C00N C00T 177.6(3) . . . . ?
C00F C00H C00O C00Q -178.1(3) . . . . ?
C00G O001 C00I O004 -30.6(2) . . . . ?
C00G O001 C00I C00S 86.0(3) . . . . ?
C00G O001 C00I C00U -147.6(2) . . . . ?
C00G C00E C00M O002 17.8(2) . . . . ?
C00G C00E C00M N006 139.5(2) . . . . ?
C00G C00L C00P O005 52.8(3) . . . . ?
C00H C00N C00T C00R 1.1(5) . . . . ?
C00H C00O C00Q C00R 0.2(5) . . . . ?
C00I O001 C00G C00E 34.1(2) . . . . ?
C00I O001 C00G C00L 146.0(2) . . . . ?
C00I O004 C00E C00G 7.6(3) . . . . ?
C00I O004 C00E C00M -104.1(2) . . . . ?
C00J N003 C00C N007 -173.6(2) . . . . ?
C00J N003 C00C C00B 4.7(3) . . . . ?
C00J N003 C00F N00A 172.5(2) . . . . ?
C00J N003 C00F C00H -9.9(4) . . . . ?
C00J N008 C00D N006 178.8(2) . . . . ?
C00J N008 C00D C00B 1.2(4) . . . . ?
C00K N006 C00D N008 -178.3(3) . . . . ?
C00K N006 C00D C00B -0.3(3) . . . . ?
C00K N006 C00M O002 68.3(3) . . . . ?
C00K N006 C00M C00E -52.7(4) . . . . ?
C00K N009 C00B C00C 176.6(3) . . . . ?
C00K N009 C00B C00D -0.2(3) . . . . ?
C00L O002 C00M N006 -129.0(2) . . . . ?
C00L O002 C00M C00E -3.9(2) . . . . ?
C00M O002 C00L C00G -11.8(3) . . . . ?
C00M O002 C00L C00P 111.1(2) . . . . ?
C00M N006 C00D N008 -3.1(4) . . . . ?
C00M N006 C00D C00B 174.9(2) . . . . ?
C00M N006 C00K N009 -174.9(2) . . . . ?
C00M C00E C00G O001 91.9(2) . . . . ?
C00M C00E C00G C00L -24.4(3) . . . . ?
C00N C00H C00O C00Q -0.8(4) . . . . ?
C00O C00H C00N C00T 0.2(4) . . . . ?
C00O C00Q C00R C00T 1.0(5) . . . . ?
C00Q C00R C00T C00N -1.7(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.235
_oxdiff_exptl_absorpt_empirical_full_min 0.700
####################################################################### 
# 
# 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_2-78
_database_code_depnum_ccdc_archive 'CCDC 2222385'
loop_
_audit_author_name
_audit_author_address
'Qi-Liang Yang'
;Henan normal university
China
;
_audit_update_record             
;
2022-11-26 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;
_audit_creation_date             2022-11-26
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 N6 O4'
_chemical_formula_sum            'C17 H16 N6 O4'
_chemical_formula_weight         368.36
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.16540(10)
_cell_length_b                   11.4212(2)
_cell_length_c                   19.8938(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1628.06(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4416
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      73.5420
_cell_measurement_theta_min      2.1810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.932
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5776
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.861
_diffrn_reflns_theta_min         4.445
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     10.00  62.00   1.00    1.00    --   40.73 -77.00-180.00   52
  2  ω    -10.00  65.00   1.00    1.00    --   40.73 -38.00  30.00   75
  3  ω    -28.00  56.00   1.00    1.00    --   40.73 -38.00 -60.00   84
  4  ω    101.00 160.00   1.00    1.00    --  107.58 125.00 -90.00   59
  5  ω     80.00 170.00   1.00    1.00    --  107.58  30.00 -30.00   90
  6  ω     59.00  88.00   1.00    1.00    --  107.58-125.00 -60.00   29
  7  ω     86.00 114.00   1.00    1.00    --  107.58-111.00 156.00   28
  8  ω     52.00  79.00   1.00    1.00    --  107.58-111.00 156.00   27
  9  ω     49.00 109.00   1.00    1.00    --  107.58 -94.00   0.00   60
 10  ω     39.00 133.00   1.00    1.00    --  107.58 -45.00 -30.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0415526000
_diffrn_orient_matrix_UB_12      0.1209004000
_diffrn_orient_matrix_UB_13      0.0308845000
_diffrn_orient_matrix_UB_21      0.0137129000
_diffrn_orient_matrix_UB_22      0.0530285000
_diffrn_orient_matrix_UB_23      -0.0710100000
_diffrn_orient_matrix_UB_31      -0.2104446000
_diffrn_orient_matrix_UB_32      0.0276932000
_diffrn_orient_matrix_UB_33      0.0015280000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                3126
_reflns_number_total             3195
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1272 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.086
_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)+(0.0377P)²+0.1738P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0761
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3A), C4(H4A), C5(H5), C6(H6), C11(H11), C12(H12)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O4(H4)
;
_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 0.57684(18) 0.71890(13) 0.66825(7) 0.0245(3) Uani 1 1 d . . . . .
O2 O 1.03905(18) 0.83156(13) 0.63995(7) 0.0267(3) Uani 1 1 d . . . . .
H2 H 1.040294 0.852641 0.680396 0.040 Uiso 1 1 calc R U . . .
O3 O 0.7164(2) 0.97343(13) 0.65633(9) 0.0337(4) Uani 1 1 d . . . . .
H3 H 0.812060 1.014318 0.649556 0.051 Uiso 1 1 calc R U . . .
O4 O 0.2873(2) 0.69286(14) 0.56793(8) 0.0341(4) Uani 1 1 d . . . . .
H4 H 0.212406 0.733126 0.590752 0.051 Uiso 1 1 calc R U . . .
N1 N 0.9721(2) 0.14752(15) 0.56922(8) 0.0265(4) Uani 1 1 d . . . . .
N2 N 0.9720(2) 0.20170(15) 0.63207(8) 0.0266(4) Uani 1 1 d . . . . .
N3 N 0.8965(2) 0.33273(14) 0.55382(8) 0.0206(3) Uani 1 1 d . . . . .
N4 N 0.8102(2) 0.53015(15) 0.56642(8) 0.0226(3) Uani 1 1 d . . . . .
N5 N 0.9193(3) 0.42690(15) 0.73255(8) 0.0263(4) Uani 1 1 d . . . . .
N6 N 0.8329(2) 0.59550(15) 0.68358(8) 0.0231(4) Uani 1 1 d . . . . .
C1 C 0.9208(3) 0.20098(18) 0.45066(10) 0.0230(4) Uani 1 1 d . . . . .
C2 C 0.9798(3) 0.28289(19) 0.40278(10) 0.0262(4) Uani 1 1 d . . . . .
H2A H 1.016879 0.359060 0.416558 0.031 Uiso 1 1 calc R U . . .
C3 C 0.9840(3) 0.2528(2) 0.33515(10) 0.0306(5) Uani 1 1 d . . . . .
H3A H 1.022342 0.308808 0.302665 0.037 Uiso 1 1 calc R U . . .
C4 C 0.9326(3) 0.1414(2) 0.31494(10) 0.0315(5) Uani 1 1 d . . . . .
H4A H 0.937274 0.121039 0.268662 0.038 Uiso 1 1 calc R U . . .
C5 C 0.8742(3) 0.05902(19) 0.36199(11) 0.0307(5) Uani 1 1 d . . . . .
H5 H 0.839074 -0.017369 0.347974 0.037 Uiso 1 1 calc R U . . .
C6 C 0.8677(3) 0.08921(18) 0.42963(11) 0.0270(4) Uani 1 1 d . . . . .
H6 H 0.826736 0.033360 0.461797 0.032 Uiso 1 1 calc R U . . .
C7 C 0.9276(3) 0.22521(17) 0.52318(10) 0.0226(4) Uani 1 1 d . . . . .
C8 C 0.9276(3) 0.31160(17) 0.62222(9) 0.0221(4) Uani 1 1 d . . . . .
C9 C 0.9023(3) 0.41048(17) 0.66418(9) 0.0219(4) Uani 1 1 d . . . . .
C10 C 0.8477(3) 0.51292(17) 0.63294(10) 0.0211(4) Uani 1 1 d . . . . .
C11 C 0.8343(3) 0.43943(17) 0.52867(10) 0.0227(4) Uani 1 1 d . . . . .
H11 H 0.808521 0.445810 0.481966 0.027 Uiso 1 1 calc R U . . .
C12 C 0.8772(3) 0.53794(19) 0.74141(10) 0.0259(4) Uani 1 1 d . . . . .
H12 H 0.877694 0.574678 0.784251 0.031 Uiso 1 1 calc R U . . .
C13 C 0.7711(3) 0.71656(18) 0.67994(9) 0.0214(4) Uani 1 1 d . . . . .
H13 H 0.797677 0.755664 0.723891 0.026 Uiso 1 1 calc R U . . .
C14 C 0.8610(3) 0.78802(18) 0.62351(10) 0.0219(4) Uani 1 1 d . . . . .
H14 H 0.873439 0.736528 0.583105 0.026 Uiso 1 1 calc R U . . .
C15 C 0.7108(3) 0.87997(19) 0.60892(10) 0.0260(4) Uani 1 1 d . . . . .
H15 H 0.719412 0.909580 0.561712 0.031 Uiso 1 1 calc R U . . .
C16 C 0.5317(3) 0.81101(17) 0.62029(9) 0.0236(4) Uani 1 1 d . . . . .
H16 H 0.436025 0.864021 0.640625 0.028 Uiso 1 1 calc R U . . .
C17 C 0.4527(3) 0.7579(2) 0.55659(10) 0.0289(4) Uani 1 1 d . . . . .
H17A H 0.427(3) 0.824(2) 0.5232(12) 0.030(6) Uiso 1 1 d . . . . .
H17B H 0.546(4) 0.701(2) 0.5323(13) 0.040(7) Uiso 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 C13 1.412(2) . ?
O1 C16 1.457(2) . ?
O2 H2 0.8400 . ?
O2 C14 1.408(2) . ?
O3 H3 0.8400 . ?
O3 C15 1.425(3) . ?
O4 H4 0.8400 . ?
O4 C17 1.417(3) . ?
N1 N2 1.395(2) . ?
N1 C7 1.314(3) . ?
N2 C8 1.310(3) . ?
N3 C7 1.389(3) . ?
N3 C8 1.400(2) . ?
N3 C11 1.391(2) . ?
N4 C10 1.365(2) . ?
N4 C11 1.291(3) . ?
N5 C9 1.378(2) . ?
N5 C12 1.315(3) . ?
N6 C10 1.384(2) . ?
N6 C12 1.362(2) . ?
N6 C13 1.454(3) . ?
C1 C2 1.400(3) . ?
C1 C6 1.396(3) . ?
C1 C7 1.470(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.389(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.384(3) . ?
C4 H4A 0.9500 . ?
C4 C5 1.392(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(3) . ?
C6 H6 0.9500 . ?
C8 C9 1.416(3) . ?
C9 C10 1.381(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13 1.0000 . ?
C13 C14 1.530(3) . ?
C14 H14 1.0000 . ?
C14 C15 1.531(3) . ?
C15 H15 1.0000 . ?
C15 C16 1.523(3) . ?
C16 H16 1.0000 . ?
C16 C17 1.515(3) . ?
C17 H17A 1.02(2) . ?
C17 H17B 1.05(3) . ?

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
C13 O1 C16 109.92(14) . . ?
C14 O2 H2 109.5 . . ?
C15 O3 H3 109.5 . . ?
C17 O4 H4 109.5 . . ?
C7 N1 N2 108.96(16) . . ?
C8 N2 N1 106.93(16) . . ?
C7 N3 C8 104.39(15) . . ?
C7 N3 C11 131.93(16) . . ?
C11 N3 C8 123.49(16) . . ?
C11 N4 C10 114.96(17) . . ?
C12 N5 C9 104.07(17) . . ?
C10 N6 C13 129.43(16) . . ?
C12 N6 C10 105.54(16) . . ?
C12 N6 C13 124.89(16) . . ?
C2 C1 C7 122.13(18) . . ?
C6 C1 C2 119.29(19) . . ?
C6 C1 C7 118.37(18) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 H2A 120.0 . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3A 119.9 . . ?
C3 C4 H4A 119.8 . . ?
C3 C4 C5 120.39(19) . . ?
C5 C4 H4A 119.8 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.6(2) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 H6 119.7 . . ?
N1 C7 N3 109.27(17) . . ?
N1 C7 C1 124.39(18) . . ?
N3 C7 C1 126.28(17) . . ?
N2 C8 N3 110.45(17) . . ?
N2 C8 C9 135.02(18) . . ?
N3 C8 C9 114.52(16) . . ?
N5 C9 C8 132.75(18) . . ?
N5 C9 C10 110.72(18) . . ?
C10 C9 C8 116.53(17) . . ?
N4 C10 N6 126.33(17) . . ?
N4 C10 C9 127.89(18) . . ?
C9 C10 N6 105.75(17) . . ?
N3 C11 H11 118.8 . . ?
N4 C11 N3 122.46(17) . . ?
N4 C11 H11 118.8 . . ?
N5 C12 N6 113.92(18) . . ?
N5 C12 H12 123.0 . . ?
N6 C12 H12 123.0 . . ?
O1 C13 N6 109.06(16) . . ?
O1 C13 H13 108.9 . . ?
O1 C13 C14 106.50(15) . . ?
N6 C13 H13 108.9 . . ?
N6 C13 C14 114.57(16) . . ?
C14 C13 H13 108.9 . . ?
O2 C14 C13 113.54(16) . . ?
O2 C14 H14 108.3 . . ?
O2 C14 C15 116.02(17) . . ?
C13 C14 H14 108.3 . . ?
C13 C14 C15 102.07(15) . . ?
C15 C14 H14 108.3 . . ?
O3 C15 C14 111.60(16) . . ?
O3 C15 H15 111.5 . . ?
O3 C15 C16 108.24(17) . . ?
C14 C15 H15 111.5 . . ?
C16 C15 C14 102.09(16) . . ?
C16 C15 H15 111.5 . . ?
O1 C16 C15 106.48(15) . . ?
O1 C16 H16 108.9 . . ?
O1 C16 C17 109.99(16) . . ?
C15 C16 H16 108.9 . . ?
C17 C16 C15 113.43(16) . . ?
C17 C16 H16 108.9 . . ?
O4 C17 C16 112.91(18) . . ?
O4 C17 H17A 110.0(14) . . ?
O4 C17 H17B 106.3(15) . . ?
C16 C17 H17A 108.4(14) . . ?
C16 C17 H17B 113.2(14) . . ?
H17A C17 H17B 105.9(19) . . ?

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 C13 C14 O2 157.46(15) . . . . ?
O1 C13 C14 C15 31.83(19) . . . . ?
O1 C16 C17 O4 60.2(2) . . . . ?
O2 C14 C15 O3 -43.6(2) . . . . ?
O2 C14 C15 C16 -158.96(16) . . . . ?
O3 C15 C16 O1 -90.78(18) . . . . ?
O3 C15 C16 C17 148.10(17) . . . . ?
N1 N2 C8 N3 0.3(2) . . . . ?
N1 N2 C8 C9 179.3(2) . . . . ?
N2 N1 C7 N3 -0.1(2) . . . . ?
N2 N1 C7 C1 177.48(17) . . . . ?
N2 C8 C9 N5 1.4(4) . . . . ?
N2 C8 C9 C10 -177.8(2) . . . . ?
N3 C8 C9 N5 -179.64(19) . . . . ?
N3 C8 C9 C10 1.1(3) . . . . ?
N5 C9 C10 N4 -177.51(18) . . . . ?
N5 C9 C10 N6 0.7(2) . . . . ?
N6 C13 C14 O2 -81.9(2) . . . . ?
N6 C13 C14 C15 152.49(16) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C2 C1 C7 N1 -142.1(2) . . . . ?
C2 C1 C7 N3 35.1(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C6 C1 C7 N1 32.8(3) . . . . ?
C6 C1 C7 N3 -150.13(19) . . . . ?
C7 N1 N2 C8 -0.2(2) . . . . ?
C7 N3 C8 N2 -0.4(2) . . . . ?
C7 N3 C8 C9 -179.56(16) . . . . ?
C7 N3 C11 N4 178.35(19) . . . . ?
C7 C1 C2 C3 175.11(18) . . . . ?
C7 C1 C6 C5 -174.55(18) . . . . ?
C8 N3 C7 N1 0.2(2) . . . . ?
C8 N3 C7 C1 -177.24(17) . . . . ?
C8 N3 C11 N4 4.1(3) . . . . ?
C8 C9 C10 N4 1.9(3) . . . . ?
C8 C9 C10 N6 -179.86(16) . . . . ?
C9 N5 C12 N6 0.3(2) . . . . ?
C10 N4 C11 N3 -0.9(3) . . . . ?
C10 N6 C12 N5 0.2(2) . . . . ?
C10 N6 C13 O1 70.9(2) . . . . ?
C10 N6 C13 C14 -48.3(3) . . . . ?
C11 N3 C7 N1 -174.85(18) . . . . ?
C11 N3 C7 C1 7.7(3) . . . . ?
C11 N3 C8 N2 175.27(17) . . . . ?
C11 N3 C8 C9 -3.9(3) . . . . ?
C11 N4 C10 N6 -179.96(18) . . . . ?
C11 N4 C10 C9 -2.0(3) . . . . ?
C12 N5 C9 C8 -179.9(2) . . . . ?
C12 N5 C9 C10 -0.6(2) . . . . ?
C12 N6 C10 N4 177.74(19) . . . . ?
C12 N6 C10 C9 -0.6(2) . . . . ?
C12 N6 C13 O1 -104.3(2) . . . . ?
C12 N6 C13 C14 136.5(2) . . . . ?
C13 O1 C16 C15 -7.6(2) . . . . ?
C13 O1 C16 C17 115.64(18) . . . . ?
C13 N6 C10 N4 1.9(3) . . . . ?
C13 N6 C10 C9 -176.44(19) . . . . ?
C13 N6 C12 N5 176.32(18) . . . . ?
C13 C14 C15 O3 80.43(19) . . . . ?
C13 C14 C15 C16 -34.98(18) . . . . ?
C14 C15 C16 O1 27.06(18) . . . . ?
C14 C15 C16 C17 -94.06(18) . . . . ?
C15 C16 C17 O4 179.31(17) . . . . ?
C16 O1 C13 N6 -139.54(15) . . . . ?
C16 O1 C13 C14 -15.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.589
_oxdiff_exptl_absorpt_empirical_full_min 0.542
####################################################################### 
# 
# 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_lww-5-20220511
_database_code_depnum_ccdc_archive 'CCDC 2222386'
loop_
_audit_author_name
_audit_author_address
'Qi-Liang Yang'
;Henan normal university
China
;
_audit_update_record             
;
2022-11-26 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;
_audit_creation_date             2022-11-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H7 Cl N4'
_chemical_formula_sum            'C11 H7 Cl N4'
_chemical_formula_weight         230.66
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Cl1 C1 N1 O1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.1946(5)
_cell_length_b                   11.1720(8)
_cell_length_c                   12.8438(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.899(6)
_cell_angle_gamma                90
_cell_volume                     1031.04(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2589
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2030
_cell_measurement_theta_min      6.1570
_shelx_estimated_absorpt_T_max   0.459
_shelx_estimated_absorpt_T_min   0.459
_exptl_absorpt_coefficient_mu    3.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4548
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.380
_diffrn_reflns_theta_min         5.250
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  13.00   1.00    1.00    --  -35.62 107.00 -52.00   92
  2  ω      9.00  79.00   1.00    1.00    --   35.62-107.00-150.00   70
  3  ω     37.00 112.00   1.00    1.00    --  107.12-107.00-150.00   75
  4  ω    101.00 177.00   1.00    1.00    --  107.12 107.00 -52.00   76
  5  ω   -108.00 -35.00   1.00    1.00    --  -35.62-178.00  60.00   73
  6  ω    -95.00 -22.00   1.00    1.00    --  -35.62 -57.00   0.00   73
  7  ω   -103.00 -35.00   1.00    1.00    --  -35.62-178.00   0.00   68
  8  ω     56.00  84.00   1.00    1.00    --   35.62  57.00 -90.00   28
  9  ω    143.00 174.00   1.00    1.00    --  107.12  61.00 150.00   31
 10  ω    118.00 170.00   1.00    1.00    --  107.12  61.00-150.00   52
 11  ω     94.00 125.00   1.00    1.00    --  107.12  61.00 120.00   31
 12  ω     38.00 107.00   1.00    1.00    --  107.12 -95.00   0.00   69
 13  ω     50.00 111.00   1.00    1.00    --  107.12-111.00 -90.00   61
 14  ω     98.00 124.00   1.00    1.00    --  107.12  61.00 150.00   26
 15  ω    137.00 164.00   1.00    1.00    --  107.12  61.00 120.00   27
 16  ω     40.00  94.00   1.00    1.00    --  107.12 -95.00 150.00   54
 17  ω     70.00 124.00   1.00    1.00    --  107.12 -61.00   0.00   54
 18  ω     39.00  66.00   1.00    1.00    --  107.12 -95.00  60.00   27
 19  ω     42.00  68.00   1.00    1.00    --  107.12 -61.00   0.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1245598000
_diffrn_orient_matrix_UB_12      0.0231257000
_diffrn_orient_matrix_UB_13      -0.0991341000
_diffrn_orient_matrix_UB_21      -0.0201033000
_diffrn_orient_matrix_UB_22      0.1321680000
_diffrn_orient_matrix_UB_23      0.0318143000
_diffrn_orient_matrix_UB_31      0.1731531000
_diffrn_orient_matrix_UB_32      0.0319601000
_diffrn_orient_matrix_UB_33      -0.0599919000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1708
_reflns_number_total             1953
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.618
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.0055(17)
_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   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1953
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0806
_refine_ls_restrained_S_all      1.144
_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)+(0.1230P)²+0.6630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2273
_refine_ls_wR_factor_ref         0.2336
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F),
 C00G(H00G)
;
_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
Cl01 Cl 0.7607(2) 0.91974(9) 0.46194(9) 0.0846(6) Uani 1 1 d . . . . .
N002 N 0.7982(3) 0.6030(2) 0.56861(18) 0.0332(6) Uani 1 1 d . . . . .
N003 N 0.7653(4) 0.6964(2) 0.50174(19) 0.0381(7) Uani 1 1 d . . . . .
N004 N 0.8277(4) 0.4252(3) 0.6361(2) 0.0508(8) Uani 1 1 d . . . . .
N005 N 0.8791(4) 0.5056(3) 0.7130(2) 0.0531(8) Uani 1 1 d . . . . .
C006 C 0.7789(4) 0.4832(3) 0.5493(2) 0.0364(7) Uani 1 1 d . . . . .
C007 C 0.7148(4) 0.4247(3) 0.4520(2) 0.0372(7) Uani 1 1 d . . . . .
C008 C 0.8609(4) 0.6132(3) 0.6720(2) 0.0405(7) Uani 1 1 d . . . . .
C009 C 0.6600(5) 0.4867(3) 0.3621(3) 0.0474(8) Uani 1 1 d . . . . .
H009 H 0.661728 0.569947 0.361997 0.057 Uiso 1 1 calc R U . . .
C00A C 0.7999(5) 0.7997(3) 0.5442(3) 0.0439(8) Uani 1 1 d . . . . .
C00B C 0.8984(5) 0.7282(4) 0.7120(2) 0.0463(8) Uani 1 1 d . . . . .
H00B H 0.944260 0.738901 0.780389 0.056 Uiso 1 1 calc R U . . .
C00C C 0.8660(5) 0.8225(3) 0.6482(3) 0.0479(9) Uani 1 1 d . . . . .
H00C H 0.886380 0.900368 0.671775 0.058 Uiso 1 1 calc R U . . .
C00D C 0.7081(5) 0.2999(3) 0.4498(3) 0.0539(9) Uani 1 1 d . . . . .
H00D H 0.741824 0.256646 0.509696 0.065 Uiso 1 1 calc R U . . .
C00E C 0.5981(5) 0.3022(4) 0.2713(3) 0.0601(11) Uani 1 1 d . . . . .
H00E H 0.558969 0.261448 0.210974 0.072 Uiso 1 1 calc R U . . .
C00F C 0.6026(6) 0.4252(4) 0.2724(3) 0.0570(10) Uani 1 1 d . . . . .
H00F H 0.566698 0.467605 0.212392 0.068 Uiso 1 1 calc R U . . .
C00G C 0.6517(6) 0.2402(4) 0.3597(4) 0.0649(11) Uani 1 1 d . . . . .
H00G H 0.650203 0.156948 0.358961 0.078 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
Cl01 C00A 1.721(4) . ?
N002 N003 1.365(3) . ?
N002 C006 1.366(4) . ?
N002 C008 1.385(4) . ?
N003 C00A 1.295(4) . ?
N004 N005 1.371(5) . ?
N004 C006 1.323(4) . ?
N005 C008 1.317(5) . ?
C006 C007 1.463(4) . ?
C007 C009 1.387(5) . ?
C007 C00D 1.395(5) . ?
C008 C00B 1.405(5) . ?
C009 H009 0.9300 . ?
C009 C00F 1.386(5) . ?
C00A C00C 1.419(5) . ?
C00B H00B 0.9300 . ?
C00B C00C 1.348(5) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00D C00G 1.380(6) . ?
C00E H00E 0.9300 . ?
C00E C00F 1.375(6) . ?
C00E C00G 1.369(7) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?

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
N003 N002 C006 128.4(2) . . ?
N003 N002 C008 125.3(3) . . ?
C006 N002 C008 106.3(3) . . ?
C00A N003 N002 113.2(3) . . ?
C006 N004 N005 109.7(3) . . ?
C008 N005 N004 107.0(3) . . ?
N002 C006 C007 128.1(3) . . ?
N004 C006 N002 107.9(3) . . ?
N004 C006 C007 124.0(3) . . ?
C009 C007 C006 123.5(3) . . ?
C009 C007 C00D 118.3(3) . . ?
C00D C007 C006 118.2(3) . . ?
N002 C008 C00B 118.3(3) . . ?
N005 C008 N002 109.2(3) . . ?
N005 C008 C00B 132.5(3) . . ?
C007 C009 H009 119.8 . . ?
C00F C009 C007 120.3(4) . . ?
C00F C009 H009 119.8 . . ?
N003 C00A Cl01 114.5(2) . . ?
N003 C00A C00C 127.2(3) . . ?
C00C C00A Cl01 118.3(3) . . ?
C008 C00B H00B 121.0 . . ?
C00C C00B C008 117.9(3) . . ?
C00C C00B H00B 121.0 . . ?
C00A C00C H00C 120.9 . . ?
C00B C00C C00A 118.1(3) . . ?
C00B C00C H00C 120.9 . . ?
C007 C00D H00D 119.7 . . ?
C00G C00D C007 120.6(4) . . ?
C00G C00D H00D 119.7 . . ?
C00F C00E H00E 120.3 . . ?
C00G C00E H00E 120.3 . . ?
C00G C00E C00F 119.5(4) . . ?
C009 C00F H00F 119.7 . . ?
C00E C00F C009 120.6(4) . . ?
C00E C00F H00F 119.7 . . ?
C00D C00G H00G 119.7 . . ?
C00E C00G C00D 120.6(4) . . ?
C00E C00G H00G 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl01 C00A C00C C00B -179.3(3) . . . . ?
N002 N003 C00A Cl01 179.8(2) . . . . ?
N002 N003 C00A C00C 0.3(5) . . . . ?
N002 C006 C007 C009 -0.9(5) . . . . ?
N002 C006 C007 C00D 179.3(3) . . . . ?
N002 C008 C00B C00C 1.9(5) . . . . ?
N003 N002 C006 N004 179.4(3) . . . . ?
N003 N002 C006 C007 -1.1(5) . . . . ?
N003 N002 C008 N005 -179.4(3) . . . . ?
N003 N002 C008 C00B -1.6(4) . . . . ?
N003 C00A C00C C00B 0.2(6) . . . . ?
N004 N005 C008 N002 -0.1(4) . . . . ?
N004 N005 C008 C00B -177.6(3) . . . . ?
N004 C006 C007 C009 178.5(3) . . . . ?
N004 C006 C007 C00D -1.3(4) . . . . ?
N005 N004 C006 N002 0.0(3) . . . . ?
N005 N004 C006 C007 -179.4(3) . . . . ?
N005 C008 C00B C00C 179.2(4) . . . . ?
C006 N002 N003 C00A -179.0(3) . . . . ?
C006 N002 C008 N005 0.2(3) . . . . ?
C006 N002 C008 C00B 178.0(3) . . . . ?
C006 N004 N005 C008 0.1(4) . . . . ?
C006 C007 C009 C00F 179.3(3) . . . . ?
C006 C007 C00D C00G -178.9(3) . . . . ?
C007 C009 C00F C00E 0.4(6) . . . . ?
C007 C00D C00G C00E -1.2(6) . . . . ?
C008 N002 N003 C00A 0.4(4) . . . . ?
C008 N002 C006 N004 -0.1(3) . . . . ?
C008 N002 C006 C007 179.3(3) . . . . ?
C008 C00B C00C C00A -1.3(5) . . . . ?
C009 C007 C00D C00G 1.3(5) . . . . ?
C00D C007 C009 C00F -0.9(5) . . . . ?
C00F C00E C00G C00D 0.7(6) . . . . ?
C00G C00E C00F C009 -0.3(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.925
_oxdiff_exptl_absorpt_empirical_full_min 0.426
