# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2478595'
loop_
_audit_author_name
_audit_author_address
'Sheng-Jiao Yan'
;Yunnan University
China
;
_audit_update_record             
;
2025-08-06 deposited with the CCDC.	2025-09-22 downloaded from the CCDC.
;
_audit_creation_date             2024-12-04
_audit_creation_method           
;
FinalCif V89 by Daniel Kratzert, Freiburg 2024,
https://dkratzert.de/finalcif.html
;
_diffrn_source_power             0.0705
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C21 H17 Cl N4 O2'
_chemical_formula_moiety         'C21 H17 Cl N4 O2'
_chemical_formula_weight         392.84
_exptl_crystal_colour_primary    colourless
_chemical_melting_point          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N3(H3), N7(H7A)
2.b Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C28(H28), C29(H29)
2.c Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C32(H32A,H32B)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C19(H19), C23(H23), C26(H26), C27(H27), C34(H34), C35(H35), C36(H36), C37(H37),
  C38(H38), C40(H40)
2.e Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C42(H42A,H42B,H42C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;

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                   21.4394(16)
_cell_length_b                   13.9197(11)
_cell_length_c                   12.5913(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.292(2)
_cell_angle_gamma                90
_cell_volume                     3624.6(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9802
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      29.60
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7203
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1110 before and 0.0585 after correction.
The Ratio of minimum to maximum transmission is 0.9657.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.956
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.41
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            66443
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_theta_min         2.225
_diffrn_reflns_theta_max         29.620
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10167
_reflns_number_gt                7896
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0276P)²+3.9295P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         10167
_refine_ls_number_parameters     507
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1125
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.753
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_
_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
Cl1 Cl 0.83736(3) 0.33500(4) 0.37453(5) 0.04110(14) Uani 1 1 d . . . . .
O1 O 0.85730(7) 0.90596(10) 0.65802(11) 0.0304(3) Uani 1 1 d . . . . .
O2 O 0.78921(6) 0.76899(9) 0.31891(10) 0.0219(3) Uani 1 1 d . . . . .
N1 N 1.00016(7) 0.74952(13) 0.38639(12) 0.0247(3) Uani 1 1 d . . . . .
N2 N 0.96153(7) 0.71616(11) 0.45014(11) 0.0188(3) Uani 1 1 d . . . . .
N3 N 0.94414(7) 0.73238(11) 0.62935(11) 0.0189(3) Uani 1 1 d . . . . .
H3 H 0.961318 0.752270 0.697114 0.023 Uiso 1 1 d R U . . .
N4 N 0.82184(7) 0.85834(10) 0.47703(11) 0.0169(3) Uani 1 1 d . . . . .
C1 C 0.93054(8) 0.62611(13) 0.42732(13) 0.0185(3) Uani 1 1 d . . . . .
C2 C 0.95999(9) 0.55225(14) 0.38453(14) 0.0244(4) Uani 1 1 d . . . . .
H2 H 0.999713 0.563473 0.366575 0.029 Uiso 1 1 calc R U . . .
C3 C 0.93159(10) 0.46217(14) 0.36792(15) 0.0283(4) Uani 1 1 d . . . . .
H3A H 0.951989 0.410906 0.340228 0.034 Uiso 1 1 calc R U . . .
C4 C 0.87327(10) 0.44824(13) 0.39227(15) 0.0258(4) Uani 1 1 d . . . . .
C5 C 0.84283(9) 0.52166(13) 0.43348(14) 0.0227(4) Uani 1 1 d . . . . .
H5 H 0.802358 0.510478 0.448803 0.027 Uiso 1 1 calc R U . . .
C6 C 0.87166(8) 0.61191(12) 0.45241(13) 0.0181(3) Uani 1 1 d . . . . .
C7 C 0.83764(8) 0.69087(12) 0.49661(14) 0.0176(3) Uani 1 1 d . . . . .
H7 H 0.798069 0.661093 0.510445 0.021 Uiso 1 1 calc R U . . .
C8 C 0.87372(8) 0.73999(12) 0.60551(14) 0.0186(3) Uani 1 1 d . . . . .
H8 H 0.859068 0.711275 0.667643 0.022 Uiso 1 1 calc R U . . .
C9 C 0.85072(8) 0.84425(13) 0.58881(14) 0.0193(3) Uani 1 1 d . . . . .
C10 C 0.81402(8) 0.77397(12) 0.41733(14) 0.0175(3) Uani 1 1 d . . . . .
C11 C 0.79252(8) 0.94915(12) 0.43285(14) 0.0195(3) Uani 1 1 d . . . . .
H11A H 0.795122 0.994057 0.494833 0.023 Uiso 1 1 calc R U . . .
H11B H 0.746164 0.937932 0.396852 0.023 Uiso 1 1 calc R U . . .
C12 C 0.82308(9) 0.99677(12) 0.35049(13) 0.0192(3) Uani 1 1 d . . . . .
C13 C 0.87252(9) 0.95516(13) 0.31383(14) 0.0210(3) Uani 1 1 d . . . . .
H13 H 0.890879 0.895996 0.344566 0.025 Uiso 1 1 calc R U . . .
C14 C 0.89540(10) 0.99969(14) 0.23212(15) 0.0258(4) Uani 1 1 d . . . . .
H14 H 0.928569 0.969920 0.206490 0.031 Uiso 1 1 calc R U . . .
C15 C 0.87007(11) 1.08706(14) 0.18812(15) 0.0287(4) Uani 1 1 d . . . . .
H15 H 0.885553 1.117142 0.132311 0.034 Uiso 1 1 calc R U . . .
C16 C 0.82178(10) 1.13012(13) 0.22656(15) 0.0269(4) Uani 1 1 d . . . . .
H16 H 0.804598 1.190441 0.197667 0.032 Uiso 1 1 calc R U . . .
C17 C 0.79845(9) 1.08536(13) 0.30717(15) 0.0233(4) Uani 1 1 d . . . . .
H17 H 0.765445 1.115439 0.332944 0.028 Uiso 1 1 calc R U . . .
C18 C 0.97304(8) 0.76442(13) 0.54858(13) 0.0188(3) Uani 1 1 d . . . . .
C19 C 1.01887(9) 0.83245(14) 0.54703(15) 0.0256(4) Uani 1 1 d . . . . .
H19 H 1.036380 0.878813 0.602210 0.031 Uiso 1 1 calc R U . . .
C20 C 1.03460(9) 0.81906(16) 0.44587(15) 0.0283(4) Uani 1 1 d . . . . .
C21 C 1.08427(12) 0.8714(2) 0.40368(19) 0.0463(6) Uani 1 1 d . . . . .
H21A H 1.087673 0.841707 0.334881 0.069 Uiso 1 1 calc R U . . .
H21B H 1.126238 0.868060 0.458469 0.069 Uiso 1 1 calc R U . . .
H21C H 1.071373 0.938826 0.390090 0.069 Uiso 1 1 calc R U . . .
Cl2 Cl 0.70456(3) 1.16091(3) 0.55767(5) 0.03334(12) Uani 1 1 d . . . . .
O3 O 0.70614(6) 0.73808(9) 0.52030(11) 0.0239(3) Uani 1 1 d . . . . .
O4 O 0.62667(8) 0.58854(11) 0.77785(13) 0.0391(4) Uani 1 1 d . . . . .
N5 N 0.50371(7) 0.78660(11) 0.39993(11) 0.0184(3) Uani 1 1 d . . . . .
N6 N 0.54174(7) 0.81162(10) 0.50291(11) 0.0163(3) Uani 1 1 d . . . . .
N7 N 0.55508(7) 0.77822(11) 0.69494(12) 0.0209(3) Uani 1 1 d . . . . .
H7A H 0.538383 0.738936 0.734840 0.025 Uiso 1 1 d R U . . .
N8 N 0.66964(7) 0.64309(10) 0.64057(11) 0.0177(3) Uani 1 1 d . . . . .
C22 C 0.65595(9) 1.05838(13) 0.54270(15) 0.0219(4) Uani 1 1 d . . . . .
C23 C 0.67710(9) 0.98021(13) 0.61045(15) 0.0209(3) Uani 1 1 d . . . . .
H23 H 0.717286 0.982861 0.664932 0.025 Uiso 1 1 calc R U . . .
C24 C 0.63921(8) 0.89757(12) 0.59845(13) 0.0178(3) Uani 1 1 d . . . . .
C25 C 0.58066(8) 0.89568(12) 0.51721(13) 0.0162(3) Uani 1 1 d . . . . .
C26 C 0.56003(8) 0.97487(13) 0.44982(14) 0.0188(3) Uani 1 1 d . . . . .
H26 H 0.520052 0.972572 0.394805 0.023 Uiso 1 1 calc R U . . .
C27 C 0.59759(9) 1.05694(13) 0.46272(14) 0.0208(3) Uani 1 1 d . . . . .
H27 H 0.583557 1.111504 0.417394 0.025 Uiso 1 1 calc R U . . .
C28 C 0.66529(8) 0.81052(12) 0.66645(14) 0.0194(3) Uani 1 1 d . . . . .
H28 H 0.706595 0.830959 0.719555 0.023 Uiso 1 1 calc R U . . .
C29 C 0.62497(9) 0.76075(13) 0.73509(14) 0.0209(3) Uani 1 1 d . . . . .
H29 H 0.640530 0.781414 0.813720 0.025 Uiso 1 1 calc R U . . .
C30 C 0.64004(9) 0.65413(14) 0.72525(15) 0.0235(4) Uani 1 1 d . . . . .
C31 C 0.68277(8) 0.72990(12) 0.59778(14) 0.0176(3) Uani 1 1 d . . . . .
C32 C 0.69303(9) 0.55094(12) 0.61254(14) 0.0196(3) Uani 1 1 d . . . . .
H32A H 0.688525 0.503175 0.668305 0.024 Uiso 1 1 calc R U . . .
H32B H 0.739711 0.557119 0.617466 0.024 Uiso 1 1 calc R U . . .
C33 C 0.65920(8) 0.51240(12) 0.49966(14) 0.0188(3) Uani 1 1 d . . . . .
C34 C 0.68629(9) 0.43252(13) 0.46144(15) 0.0224(4) Uani 1 1 d . . . . .
H34 H 0.724502 0.404268 0.506494 0.027 Uiso 1 1 calc R U . . .
C35 C 0.65790(9) 0.39401(14) 0.35821(16) 0.0255(4) Uani 1 1 d . . . . .
H35 H 0.676933 0.340064 0.332725 0.031 Uiso 1 1 calc R U . . .
C36 C 0.60168(9) 0.43436(14) 0.29221(15) 0.0237(4) Uani 1 1 d . . . . .
H36 H 0.582248 0.408376 0.221449 0.028 Uiso 1 1 calc R U . . .
C37 C 0.57414(9) 0.51283(13) 0.33039(15) 0.0242(4) Uani 1 1 d . . . . .
H37 H 0.535468 0.540218 0.285782 0.029 Uiso 1 1 calc R U . . .
C38 C 0.60275(9) 0.55183(13) 0.43366(15) 0.0219(4) Uani 1 1 d . . . . .
H38 H 0.583523 0.605648 0.459027 0.026 Uiso 1 1 calc R U . . .
C39 C 0.52621(8) 0.75819(12) 0.58399(14) 0.0189(3) Uani 1 1 d . . . . .
C40 C 0.47751(9) 0.69695(13) 0.53276(15) 0.0216(3) Uani 1 1 d . . . . .
H40 H 0.456562 0.650364 0.566441 0.026 Uiso 1 1 calc R U . . .
C41 C 0.46507(8) 0.71772(13) 0.41933(15) 0.0200(3) Uani 1 1 d . . . . .
C42 C 0.41614(9) 0.67171(15) 0.32588(16) 0.0275(4) Uani 1 1 d . . . . .
H42A H 0.416922 0.703351 0.256719 0.041 Uiso 1 1 calc R U . . .
H42B H 0.372994 0.678221 0.337873 0.041 Uiso 1 1 calc R U . . .
H42C H 0.426503 0.603451 0.321928 0.041 Uiso 1 1 calc R U . . .


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
Cl1 C4 1.743(2) . ?
O1 C9 1.205(2) . ?
O2 C10 1.215(2) . ?
N1 N2 1.377(2) . ?
N1 C20 1.323(2) . ?
N2 C1 1.412(2) . ?
N2 C18 1.374(2) . ?
N3 H3 0.8800 . ?
N3 C8 1.463(2) . ?
N3 C18 1.396(2) . ?
N4 C9 1.394(2) . ?
N4 C10 1.381(2) . ?
N4 C11 1.455(2) . ?
C1 C2 1.388(2) . ?
C1 C6 1.394(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.377(3) . ?
C4 C5 1.385(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(2) . ?
C6 C7 1.504(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.545(2) . ?
C7 C10 1.525(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.529(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.517(2) . ?
C12 C13 1.389(2) . ?
C12 C17 1.395(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.396(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.392(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.368(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.413(3) . ?
C20 C21 1.499(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
Cl2 C22 1.7479(18) . ?
O3 C31 1.214(2) . ?
O4 C30 1.206(2) . ?
N5 N6 1.3819(19) . ?
N5 C41 1.331(2) . ?
N6 C25 1.421(2) . ?
N6 C39 1.373(2) . ?
N7 H7A 0.8800 . ?
N7 C29 1.470(2) . ?
N7 C39 1.399(2) . ?
N8 C30 1.386(2) . ?
N8 C31 1.382(2) . ?
N8 C32 1.454(2) . ?
C22 C23 1.383(3) . ?
C22 C27 1.384(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.393(2) . ?
C24 C25 1.395(2) . ?
C24 C28 1.504(2) . ?
C25 C26 1.390(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.382(2) . ?
C27 H27 0.9500 . ?
C28 H28 1.0000 . ?
C28 C29 1.539(2) . ?
C28 C31 1.523(2) . ?
C29 H29 1.0000 . ?
C29 C30 1.531(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.513(2) . ?
C33 C34 1.397(2) . ?
C33 C38 1.388(2) . ?
C34 H34 0.9500 . ?
C34 C35 1.389(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.389(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.387(3) . ?
C37 H37 0.9500 . ?
C37 C38 1.393(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.370(3) . ?
C40 H40 0.9500 . ?
C40 C41 1.412(2) . ?
C41 C42 1.498(3) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 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
C20 N1 N2 104.37(14) . . ?
N1 N2 C1 120.24(14) . . ?
C18 N2 N1 111.62(14) . . ?
C18 N2 C1 125.49(14) . . ?
C8 N3 H3 108.8 . . ?
C18 N3 H3 116.9 . . ?
C18 N3 C8 117.35(13) . . ?
C9 N4 C11 122.70(14) . . ?
C10 N4 C9 112.83(14) . . ?
C10 N4 C11 123.54(14) . . ?
C2 C1 N2 119.92(16) . . ?
C2 C1 C6 121.00(17) . . ?
C6 C1 N2 119.03(15) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.15(18) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3A 120.6 . . ?
C4 C3 C2 118.84(17) . . ?
C4 C3 H3A 120.6 . . ?
C3 C4 Cl1 119.68(15) . . ?
C3 C4 C5 121.64(18) . . ?
C5 C4 Cl1 118.65(16) . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.87(18) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C7 122.45(15) . . ?
C5 C6 C1 118.47(16) . . ?
C5 C6 C7 119.06(16) . . ?
C6 C7 H7 106.1 . . ?
C6 C7 C8 118.27(14) . . ?
C6 C7 C10 114.95(14) . . ?
C8 C7 H7 106.1 . . ?
C10 C7 H7 106.1 . . ?
C10 C7 C8 104.33(13) . . ?
N3 C8 C7 113.45(13) . . ?
N3 C8 H8 109.3 . . ?
N3 C8 C9 112.00(14) . . ?
C7 C8 H8 109.3 . . ?
C9 C8 C7 103.31(13) . . ?
C9 C8 H8 109.3 . . ?
O1 C9 N4 124.47(16) . . ?
O1 C9 C8 127.23(16) . . ?
N4 C9 C8 108.27(14) . . ?
O2 C10 N4 124.17(16) . . ?
O2 C10 C7 127.23(16) . . ?
N4 C10 C7 108.49(14) . . ?
N4 C11 H11A 108.6 . . ?
N4 C11 H11B 108.6 . . ?
N4 C11 C12 114.84(14) . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C13 C12 C11 123.34(15) . . ?
C13 C12 C17 118.82(17) . . ?
C17 C12 C11 117.81(16) . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.45(17) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.47(18) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.26(18) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.35(18) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 119.7 . . ?
C16 C17 C12 120.62(18) . . ?
C16 C17 H17 119.7 . . ?
N2 C18 N3 119.49(15) . . ?
C19 C18 N2 106.52(15) . . ?
C19 C18 N3 133.61(16) . . ?
C18 C19 H19 127.3 . . ?
C18 C19 C20 105.34(16) . . ?
C20 C19 H19 127.3 . . ?
N1 C20 C19 112.12(16) . . ?
N1 C20 C21 119.84(18) . . ?
C19 C20 C21 128.03(19) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C41 N5 N6 104.55(13) . . ?
N5 N6 C25 120.53(13) . . ?
C39 N6 N5 111.24(14) . . ?
C39 N6 C25 126.96(14) . . ?
C29 N7 H7A 103.4 . . ?
C39 N7 H7A 107.9 . . ?
C39 N7 C29 116.94(14) . . ?
C30 N8 C32 122.81(14) . . ?
C31 N8 C30 112.63(14) . . ?
C31 N8 C32 123.91(14) . . ?
C23 C22 Cl2 119.12(14) . . ?
C23 C22 C27 121.58(17) . . ?
C27 C22 Cl2 119.29(14) . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 119.72(16) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C25 118.77(16) . . ?
C23 C24 C28 119.02(15) . . ?
C25 C24 C28 121.99(16) . . ?
C24 C25 N6 119.57(15) . . ?
C26 C25 N6 119.60(15) . . ?
C26 C25 C24 120.83(16) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 C25 120.13(16) . . ?
C27 C26 H26 119.9 . . ?
C22 C27 H27 120.5 . . ?
C26 C27 C22 118.96(16) . . ?
C26 C27 H27 120.5 . . ?
C24 C28 H28 106.4 . . ?
C24 C28 C29 120.20(15) . . ?
C24 C28 C31 112.38(14) . . ?
C29 C28 H28 106.4 . . ?
C31 C28 H28 106.4 . . ?
C31 C28 C29 104.24(14) . . ?
N7 C29 C28 113.89(14) . . ?
N7 C29 H29 109.7 . . ?
N7 C29 C30 110.50(15) . . ?
C28 C29 H29 109.7 . . ?
C30 C29 C28 103.25(14) . . ?
C30 C29 H29 109.7 . . ?
O4 C30 N8 124.19(17) . . ?
O4 C30 C29 127.14(17) . . ?
N8 C30 C29 108.60(15) . . ?
O3 C31 N8 124.40(16) . . ?
O3 C31 C28 127.08(16) . . ?
N8 C31 C28 108.49(14) . . ?
N8 C32 H32A 108.4 . . ?
N8 C32 H32B 108.4 . . ?
N8 C32 C33 115.47(14) . . ?
H32A C32 H32B 107.5 . . ?
C33 C32 H32A 108.4 . . ?
C33 C32 H32B 108.4 . . ?
C34 C33 C32 117.76(15) . . ?
C38 C33 C32 123.25(16) . . ?
C38 C33 C34 118.98(16) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 C33 120.66(17) . . ?
C35 C34 H34 119.7 . . ?
C34 C35 H35 120.0 . . ?
C34 C35 C36 120.03(17) . . ?
C36 C35 H35 120.0 . . ?
C35 C36 H36 120.2 . . ?
C37 C36 C35 119.52(17) . . ?
C37 C36 H36 120.2 . . ?
C36 C37 H37 119.7 . . ?
C36 C37 C38 120.50(17) . . ?
C38 C37 H37 119.7 . . ?
C33 C38 C37 120.30(17) . . ?
C33 C38 H38 119.9 . . ?
C37 C38 H38 119.9 . . ?
N6 C39 N7 120.29(16) . . ?
C40 C39 N6 106.92(15) . . ?
C40 C39 N7 132.51(16) . . ?
C39 C40 H40 127.3 . . ?
C39 C40 C41 105.43(15) . . ?
C41 C40 H40 127.3 . . ?
N5 C41 C40 111.86(15) . . ?
N5 C41 C42 120.31(16) . . ?
C40 C41 C42 127.83(16) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 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
Cl1 C4 C5 C6 177.58(13) . . . . ?
N1 N2 C1 C2 32.3(2) . . . . ?
N1 N2 C1 C6 -150.18(16) . . . . ?
N1 N2 C18 N3 -172.09(15) . . . . ?
N1 N2 C18 C19 1.8(2) . . . . ?
N2 N1 C20 C19 -0.5(2) . . . . ?
N2 N1 C20 C21 178.3(2) . . . . ?
N2 C1 C2 C3 176.29(16) . . . . ?
N2 C1 C6 C5 -177.55(15) . . . . ?
N2 C1 C6 C7 3.8(2) . . . . ?
N2 C18 C19 C20 -1.9(2) . . . . ?
N3 C8 C9 O1 -70.9(2) . . . . ?
N3 C8 C9 N4 107.13(15) . . . . ?
N3 C18 C19 C20 170.68(19) . . . . ?
N4 C11 C12 C13 3.9(2) . . . . ?
N4 C11 C12 C17 -178.28(15) . . . . ?
C1 N2 C18 N3 -10.7(3) . . . . ?
C1 N2 C18 C19 163.18(16) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C1 C6 C7 C8 -58.6(2) . . . . ?
C1 C6 C7 C10 65.4(2) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
C2 C1 C6 C7 -178.66(16) . . . . ?
C2 C3 C4 Cl1 -178.80(14) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C4 C5 C6 C7 179.67(16) . . . . ?
C5 C6 C7 C8 122.78(17) . . . . ?
C5 C6 C7 C10 -113.16(17) . . . . ?
C6 C1 C2 C3 -1.2(3) . . . . ?
C6 C7 C8 N3 23.7(2) . . . . ?
C6 C7 C8 C9 145.17(15) . . . . ?
C6 C7 C10 O2 40.4(2) . . . . ?
C6 C7 C10 N4 -143.14(15) . . . . ?
C7 C8 C9 O1 166.61(18) . . . . ?
C7 C8 C9 N4 -15.32(17) . . . . ?
C8 N3 C18 N2 -66.7(2) . . . . ?
C8 N3 C18 C19 121.5(2) . . . . ?
C8 C7 C10 O2 171.55(17) . . . . ?
C8 C7 C10 N4 -11.99(17) . . . . ?
C9 N4 C10 O2 179.02(16) . . . . ?
C9 N4 C10 C7 2.42(19) . . . . ?
C9 N4 C11 C12 118.79(17) . . . . ?
C10 N4 C9 O1 -173.36(17) . . . . ?
C10 N4 C9 C8 8.50(19) . . . . ?
C10 N4 C11 C12 -73.1(2) . . . . ?
C10 C7 C8 N3 -105.49(15) . . . . ?
C10 C7 C8 C9 16.00(16) . . . . ?
C11 N4 C9 O1 -4.1(3) . . . . ?
C11 N4 C9 C8 177.79(14) . . . . ?
C11 N4 C10 O2 9.8(3) . . . . ?
C11 N4 C10 C7 -166.76(14) . . . . ?
C11 C12 C13 C14 175.45(17) . . . . ?
C11 C12 C17 C16 -176.23(16) . . . . ?
C12 C13 C14 C15 1.4(3) . . . . ?
C13 C12 C17 C16 1.7(3) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
C15 C16 C17 C12 0.0(3) . . . . ?
C17 C12 C13 C14 -2.3(3) . . . . ?
C18 N2 C1 C2 -127.66(18) . . . . ?
C18 N2 C1 C6 49.9(2) . . . . ?
C18 N3 C8 C7 54.5(2) . . . . ?
C18 N3 C8 C9 -62.01(19) . . . . ?
C18 C19 C20 N1 1.6(2) . . . . ?
C18 C19 C20 C21 -177.1(2) . . . . ?
C20 N1 N2 C1 -163.31(16) . . . . ?
C20 N1 N2 C18 -0.8(2) . . . . ?
Cl2 C22 C23 C24 -179.18(13) . . . . ?
Cl2 C22 C27 C26 178.66(13) . . . . ?
N5 N6 C25 C24 -148.15(15) . . . . ?
N5 N6 C25 C26 31.6(2) . . . . ?
N5 N6 C39 N7 -174.28(14) . . . . ?
N5 N6 C39 C40 0.38(19) . . . . ?
N6 N5 C41 C40 -0.43(19) . . . . ?
N6 N5 C41 C42 -179.94(15) . . . . ?
N6 C25 C26 C27 -179.79(15) . . . . ?
N6 C39 C40 C41 -0.61(19) . . . . ?
N7 C29 C30 O4 -69.2(3) . . . . ?
N7 C29 C30 N8 107.99(16) . . . . ?
N7 C39 C40 C41 173.14(18) . . . . ?
N8 C32 C33 C34 169.85(15) . . . . ?
N8 C32 C33 C38 -10.8(2) . . . . ?
C22 C23 C24 C25 0.4(2) . . . . ?
C22 C23 C24 C28 175.13(16) . . . . ?
C23 C22 C27 C26 -0.7(3) . . . . ?
C23 C24 C25 N6 179.27(15) . . . . ?
C23 C24 C25 C26 -0.5(2) . . . . ?
C23 C24 C28 C29 127.93(17) . . . . ?
C23 C24 C28 C31 -108.88(18) . . . . ?
C24 C25 C26 C27 0.0(2) . . . . ?
C24 C28 C29 N7 23.4(2) . . . . ?
C24 C28 C29 C30 143.30(16) . . . . ?
C24 C28 C31 O3 36.6(2) . . . . ?
C24 C28 C31 N8 -145.47(15) . . . . ?
C25 N6 C39 N7 -7.2(3) . . . . ?
C25 N6 C39 C40 167.45(16) . . . . ?
C25 C24 C28 C29 -57.5(2) . . . . ?
C25 C24 C28 C31 65.6(2) . . . . ?
C25 C26 C27 C22 0.6(2) . . . . ?
C27 C22 C23 C24 0.2(3) . . . . ?
C28 C24 C25 N6 4.7(2) . . . . ?
C28 C24 C25 C26 -175.03(15) . . . . ?
C28 C29 C30 O4 168.7(2) . . . . ?
C28 C29 C30 N8 -14.18(19) . . . . ?
C29 N7 C39 N6 -66.4(2) . . . . ?
C29 N7 C39 C40 120.5(2) . . . . ?
C29 C28 C31 O3 168.32(17) . . . . ?
C29 C28 C31 N8 -13.73(17) . . . . ?
C30 N8 C31 O3 -176.93(17) . . . . ?
C30 N8 C31 C28 5.06(19) . . . . ?
C30 N8 C32 C33 115.42(18) . . . . ?
C31 N8 C30 O4 -176.69(19) . . . . ?
C31 N8 C30 C29 6.1(2) . . . . ?
C31 N8 C32 C33 -74.5(2) . . . . ?
C31 C28 C29 N7 -103.59(16) . . . . ?
C31 C28 C29 C30 16.27(17) . . . . ?
C32 N8 C30 O4 -5.6(3) . . . . ?
C32 N8 C30 C29 177.11(15) . . . . ?
C32 N8 C31 O3 12.1(3) . . . . ?
C32 N8 C31 C28 -165.88(15) . . . . ?
C32 C33 C34 C35 -179.53(17) . . . . ?
C32 C33 C38 C37 179.91(17) . . . . ?
C33 C34 C35 C36 -0.6(3) . . . . ?
C34 C33 C38 C37 -0.8(3) . . . . ?
C34 C35 C36 C37 -0.3(3) . . . . ?
C35 C36 C37 C38 0.6(3) . . . . ?
C36 C37 C38 C33 -0.1(3) . . . . ?
C38 C33 C34 C35 1.1(3) . . . . ?
C39 N6 C25 C24 45.9(2) . . . . ?
C39 N6 C25 C26 -134.36(17) . . . . ?
C39 N7 C29 C28 53.2(2) . . . . ?
C39 N7 C29 C30 -62.51(19) . . . . ?
C39 C40 C41 N5 0.7(2) . . . . ?
C39 C40 C41 C42 -179.87(18) . . . . ?
C41 N5 N6 C25 -167.98(14) . . . . ?
C41 N5 N6 C39 0.03(18) . . . . ?

####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2478597'
loop_
_audit_author_name
_audit_author_address
'Sheng-Jiao Yan'
;Yunnan University
China
;
_audit_update_record             
;
2025-08-06 deposited with the CCDC.	2025-09-22 downloaded from the CCDC.
;
_audit_creation_date             2024-11-13
_audit_creation_method           
;
FinalCif V89 by Daniel Kratzert, Freiburg 2024,
https://dkratzert.de/finalcif.html
;
_diffrn_source_power             0.07
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C21 H21 Cl N4 O4'
_chemical_formula_moiety         'C21 H17 Cl N4 O2, 2(H2 O)'
_chemical_formula_weight         428.87
_exptl_crystal_colour_primary    colourless
_chemical_melting_point          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Riding coordinates:
 O4(H4A,H4B)
2.b Free rotating group:
 O3(H3A,H3B)
2.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B)
2.d Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C5(H5), C13(H13), C15(H15), C16(H16),
  C19(H19)
2.e Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;

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                   9.5672(9)
_cell_length_b                   35.984(3)
_cell_length_c                   5.9462(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.563(3)
_cell_angle_gamma                90
_cell_volume                     2037.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      28.20
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5785
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1323 before and 0.0968 after correction.
The Ratio of minimum to maximum transmission is 0.7758.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.965
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            27229
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_theta_min         2.139
_diffrn_reflns_theta_max         28.420
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5069
_reflns_number_gt                4241
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0045P)²+14.2552P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5069
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1273
_refine_ls_R_factor_gt           0.1120
_refine_ls_wR_factor_ref         0.2344
_refine_ls_wR_factor_gt          0.2267
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.406
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_
_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
Cl1 Cl 0.47992(13) 0.57017(3) -0.09168(19) 0.0298(3) Uani 1 1 d . . . . .
O1 O 0.8110(3) 0.61670(9) 0.8228(5) 0.0268(7) Uani 1 1 d . . . . .
O2 O 1.0457(4) 0.62349(11) 0.1944(6) 0.0350(8) Uani 1 1 d . . . . .
N1 N 0.9306(4) 0.60988(10) 0.5080(6) 0.0233(8) Uani 1 1 d . . . . .
N2 N 0.7368(4) 0.69131(10) 0.6254(7) 0.0248(8) Uani 1 1 d . . . . .
H2 H 0.793727 0.710466 0.622345 0.030 Uiso 1 1 calc R U . . .
N3 N 0.5099(4) 0.67143(10) 0.6940(6) 0.0218(8) Uani 1 1 d . . . . .
N4 N 0.4037(4) 0.67797(11) 0.8293(6) 0.0246(8) Uani 1 1 d . . . . .
C1 C 0.8838(5) 0.52257(14) 0.7639(8) 0.0306(10) Uani 1 1 d . . . . .
H1 H 0.943609 0.527411 0.897669 0.037 Uiso 1 1 calc R U . . .
C2 C 0.7847(6) 0.49450(15) 0.7618(9) 0.0366(12) Uani 1 1 d . . . . .
H2A H 0.778714 0.479798 0.893223 0.044 Uiso 1 1 calc R U . . .
C3 C 0.6938(6) 0.48762(14) 0.5689(10) 0.0380(12) Uani 1 1 d . . . . .
H3 H 0.624314 0.468785 0.569733 0.046 Uiso 1 1 calc R U . . .
C4 C 0.7057(6) 0.50846(14) 0.3762(9) 0.0349(12) Uani 1 1 d . . . . .
H4 H 0.645276 0.503726 0.242901 0.042 Uiso 1 1 calc R U . . .
C5 C 0.8065(6) 0.53637(13) 0.3782(8) 0.0302(10) Uani 1 1 d . . . . .
H5 H 0.814127 0.550647 0.245584 0.036 Uiso 1 1 calc R U . . .
C6 C 0.8961(5) 0.54368(13) 0.5715(8) 0.0253(9) Uani 1 1 d . . . . .
C7 C 1.0014(5) 0.57525(13) 0.5762(8) 0.0282(10) Uani 1 1 d . . . . .
H7A H 1.049173 0.577916 0.730581 0.034 Uiso 1 1 calc R U . . .
H7B H 1.073418 0.569592 0.472350 0.034 Uiso 1 1 calc R U . . .
C8 C 0.9575(5) 0.63109(14) 0.3234(8) 0.0258(10) Uani 1 1 d . . . . .
C9 C 0.8639(5) 0.66500(13) 0.3145(8) 0.0259(9) Uani 1 1 d . . . . .
H9A H 0.813085 0.667866 0.162409 0.031 Uiso 1 1 calc R U . . .
H9B H 0.919932 0.687720 0.351059 0.031 Uiso 1 1 calc R U . . .
C10 C 0.7596(5) 0.65807(12) 0.4938(7) 0.0225(9) Uani 1 1 d . . . . .
C11 C 0.8344(4) 0.62650(12) 0.6365(7) 0.0211(8) Uani 1 1 d . . . . .
C12 C 0.6206(5) 0.64135(12) 0.3963(7) 0.0228(9) Uani 1 1 d . . . . .
C13 C 0.6126(5) 0.61765(12) 0.2106(7) 0.0218(9) Uani 1 1 d . . . . .
H13 H 0.693246 0.613347 0.132772 0.026 Uiso 1 1 calc R U . . .
C14 C 0.4864(5) 0.60033(12) 0.1395(7) 0.0223(9) Uani 1 1 d . . . . .
C15 C 0.3664(5) 0.60646(12) 0.2450(7) 0.0232(9) Uani 1 1 d . . . . .
H15 H 0.280781 0.594650 0.191626 0.028 Uiso 1 1 calc R U . . .
C16 C 0.3722(5) 0.63024(12) 0.4313(8) 0.0229(9) Uani 1 1 d . . . . .
H16 H 0.290418 0.634858 0.505744 0.027 Uiso 1 1 calc R U . . .
C17 C 0.4990(5) 0.64708(11) 0.5066(7) 0.0208(8) Uani 1 1 d . . . . .
C18 C 0.6249(5) 0.69231(12) 0.7545(8) 0.0231(9) Uani 1 1 d . . . . .
C19 C 0.5963(5) 0.71332(12) 0.9379(8) 0.0246(9) Uani 1 1 d . . . . .
H19 H 0.656427 0.730633 1.019897 0.030 Uiso 1 1 calc R U . . .
C20 C 0.4572(5) 0.70344(12) 0.9777(8) 0.0272(10) Uani 1 1 d . . . . .
C21 C 0.3696(6) 0.71827(14) 1.1542(8) 0.0342(11) Uani 1 1 d . . . . .
H21A H 0.338654 0.743563 1.113614 0.051 Uiso 1 1 calc R U . . .
H21B H 0.425548 0.718616 1.301175 0.051 Uiso 1 1 calc R U . . .
H21C H 0.287296 0.702284 1.162775 0.051 Uiso 1 1 calc R U . . .
O3 O 0.1129(4) 0.66507(11) 0.8102(7) 0.0385(9) Uani 1 1 d G . . . .
H3A H 0.203432 0.664781 0.804626 0.058 Uiso 1 1 d G U . . .
H3B H 0.099881 0.653187 0.933723 0.058 Uiso 1 1 d G U . . .
O4 O -0.0122(6) 0.73315(14) 0.8093(14) 0.105(3) Uani 1 1 d . . . . .
H4A H 0.061735 0.721287 0.868066 0.158 Uiso 1 1 d R U . . .
H4B H -0.042465 0.745077 0.922276 0.158 Uiso 1 1 d R U . . .


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
Cl1 C14 1.748(4) . ?
O1 C11 1.204(5) . ?
O2 C8 1.225(6) . ?
N1 C7 1.457(6) . ?
N1 C8 1.382(6) . ?
N1 C11 1.387(6) . ?
N2 H2 0.8800 . ?
N2 C10 1.457(6) . ?
N2 C18 1.377(6) . ?
N3 N4 1.375(5) . ?
N3 C17 1.414(6) . ?
N3 C18 1.352(5) . ?
N4 C20 1.339(6) . ?
C1 H1 0.9500 . ?
C1 C2 1.384(8) . ?
C1 C6 1.388(7) . ?
C2 H2A 0.9500 . ?
C2 C3 1.393(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(6) . ?
C6 C7 1.517(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.511(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.550(7) . ?
C10 C11 1.551(6) . ?
C10 C12 1.522(6) . ?
C12 C13 1.391(6) . ?
C12 C17 1.405(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(6) . ?
C14 C15 1.378(7) . ?
C15 H15 0.9500 . ?
C15 C16 1.396(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(6) . ?
C18 C19 1.376(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.419(7) . ?
C20 C21 1.503(7) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O3 H3A 0.8698 . ?
O3 H3B 0.8694 . ?
O4 H4A 0.8700 . ?
O4 H4B 0.8703 . ?

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
C8 N1 C7 125.2(4) . . ?
C8 N1 C11 112.6(4) . . ?
C11 N1 C7 122.1(4) . . ?
C10 N2 H2 120.5 . . ?
C18 N2 H2 120.5 . . ?
C18 N2 C10 119.1(4) . . ?
N4 N3 C17 124.4(4) . . ?
C18 N3 N4 112.2(4) . . ?
C18 N3 C17 123.4(4) . . ?
C20 N4 N3 104.3(4) . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.3(5) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2A 119.7 . . ?
C1 C2 C3 120.6(5) . . ?
C3 C2 H2A 119.7 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.4(5) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(5) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(5) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.9(5) . . ?
C1 C6 C7 120.3(4) . . ?
C5 C6 C7 120.8(4) . . ?
N1 C7 C6 110.2(4) . . ?
N1 C7 H7A 109.6 . . ?
N1 C7 H7B 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
O2 C8 N1 124.5(5) . . ?
O2 C8 C9 126.9(5) . . ?
N1 C8 C9 108.6(4) . . ?
C8 C9 H9A 110.7 . . ?
C8 C9 H9B 110.7 . . ?
C8 C9 C10 105.4(4) . . ?
H9A C9 H9B 108.8 . . ?
C10 C9 H9A 110.7 . . ?
C10 C9 H9B 110.7 . . ?
N2 C10 C9 112.2(4) . . ?
N2 C10 C11 113.1(4) . . ?
N2 C10 C12 111.0(4) . . ?
C9 C10 C11 101.5(4) . . ?
C12 C10 C9 113.5(4) . . ?
C12 C10 C11 105.0(3) . . ?
O1 C11 N1 124.9(4) . . ?
O1 C11 C10 126.9(4) . . ?
N1 C11 C10 108.1(4) . . ?
C13 C12 C10 121.6(4) . . ?
C13 C12 C17 118.4(4) . . ?
C17 C12 C10 119.8(4) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.7(4) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 Cl1 118.8(4) . . ?
C15 C14 Cl1 119.3(3) . . ?
C15 C14 C13 121.9(4) . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.3(4) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.2(4) . . ?
C17 C16 H16 120.4 . . ?
C12 C17 N3 117.3(4) . . ?
C16 C17 N3 121.3(4) . . ?
C16 C17 C12 121.5(4) . . ?
N3 C18 N2 119.6(4) . . ?
N3 C18 C19 107.3(4) . . ?
C19 C18 N2 133.0(4) . . ?
C18 C19 H19 127.6 . . ?
C18 C19 C20 104.9(4) . . ?
C20 C19 H19 127.6 . . ?
N4 C20 C19 111.5(4) . . ?
N4 C20 C21 120.0(5) . . ?
C19 C20 C21 128.5(4) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H3A O3 H3B 104.5 . . ?
H4A O4 H4B 104.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C14 C15 C16 179.3(3) . . . . ?
O2 C8 C9 C10 172.4(4) . . . . ?
N1 C8 C9 C10 -9.4(5) . . . . ?
N2 C10 C11 O1 42.7(6) . . . . ?
N2 C10 C11 N1 -140.0(4) . . . . ?
N2 C10 C12 C13 158.9(4) . . . . ?
N2 C10 C12 C17 -26.9(5) . . . . ?
N2 C18 C19 C20 174.3(5) . . . . ?
N3 N4 C20 C19 0.2(5) . . . . ?
N3 N4 C20 C21 179.0(4) . . . . ?
N3 C18 C19 C20 -0.5(5) . . . . ?
N4 N3 C17 C12 -175.3(4) . . . . ?
N4 N3 C17 C16 6.3(6) . . . . ?
N4 N3 C18 N2 -174.9(4) . . . . ?
N4 N3 C18 C19 0.7(5) . . . . ?
C1 C2 C3 C4 1.8(8) . . . . ?
C1 C6 C7 N1 -123.6(5) . . . . ?
C2 C1 C6 C5 0.7(7) . . . . ?
C2 C1 C6 C7 178.0(5) . . . . ?
C2 C3 C4 C5 -1.0(8) . . . . ?
C3 C4 C5 C6 0.1(8) . . . . ?
C4 C5 C6 C1 0.1(7) . . . . ?
C4 C5 C6 C7 -177.2(5) . . . . ?
C5 C6 C7 N1 53.6(6) . . . . ?
C6 C1 C2 C3 -1.6(8) . . . . ?
C7 N1 C8 O2 -0.7(7) . . . . ?
C7 N1 C8 C9 -179.0(4) . . . . ?
C7 N1 C11 O1 8.2(7) . . . . ?
C7 N1 C11 C10 -169.2(4) . . . . ?
C8 N1 C7 C6 -119.2(5) . . . . ?
C8 N1 C11 O1 -167.4(4) . . . . ?
C8 N1 C11 C10 15.2(5) . . . . ?
C8 C9 C10 N2 137.9(4) . . . . ?
C8 C9 C10 C11 16.9(4) . . . . ?
C8 C9 C10 C12 -95.3(4) . . . . ?
C9 C10 C11 O1 163.1(4) . . . . ?
C9 C10 C11 N1 -19.6(4) . . . . ?
C9 C10 C12 C13 31.5(6) . . . . ?
C9 C10 C12 C17 -154.3(4) . . . . ?
C10 N2 C18 N3 -26.8(6) . . . . ?
C10 N2 C18 C19 158.9(5) . . . . ?
C10 C12 C13 C14 174.2(4) . . . . ?
C10 C12 C17 N3 5.9(6) . . . . ?
C10 C12 C17 C16 -175.7(4) . . . . ?
C11 N1 C7 C6 65.8(5) . . . . ?
C11 N1 C8 O2 174.7(4) . . . . ?
C11 N1 C8 C9 -3.6(5) . . . . ?
C11 C10 C12 C13 -78.6(5) . . . . ?
C11 C10 C12 C17 95.7(5) . . . . ?
C12 C10 C11 O1 -78.5(5) . . . . ?
C12 C10 C11 N1 98.9(4) . . . . ?
C12 C13 C14 Cl1 -179.1(3) . . . . ?
C12 C13 C14 C15 1.4(7) . . . . ?
C13 C12 C17 N3 -179.7(4) . . . . ?
C13 C12 C17 C16 -1.3(6) . . . . ?
C13 C14 C15 C16 -1.2(7) . . . . ?
C14 C15 C16 C17 -0.2(6) . . . . ?
C15 C16 C17 N3 179.8(4) . . . . ?
C15 C16 C17 C12 1.5(6) . . . . ?
C17 N3 N4 C20 -177.8(4) . . . . ?
C17 N3 C18 N2 2.3(6) . . . . ?
C17 N3 C18 C19 177.9(4) . . . . ?
C17 C12 C13 C14 -0.2(6) . . . . ?
C18 N2 C10 C9 165.5(4) . . . . ?
C18 N2 C10 C11 -80.4(5) . . . . ?
C18 N2 C10 C12 37.3(5) . . . . ?
C18 N3 N4 C20 -0.6(5) . . . . ?
C18 N3 C17 C12 7.8(6) . . . . ?
C18 N3 C17 C16 -170.6(4) . . . . ?
C18 C19 C20 N4 0.2(5) . . . . ?
C18 C19 C20 C21 -178.5(4) . . . . ?

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

data_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2478596'
loop_
_audit_author_name
_audit_author_address
'Sheng-Jiao Yan'
;Yunnan University
China
;
_audit_update_record             
;
2025-08-06 deposited with the CCDC.	2025-09-22 downloaded from the CCDC.
;
_audit_creation_date             2025-04-21
_audit_creation_method           
;
FinalCif V89 by Daniel Kratzert, Freiburg 2025,
https://dkratzert.de/finalcif.html
;
_diffrn_source_power             0.07
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C14 H14 N4 O'
_chemical_formula_moiety         'C14 H14 N4 O'
_chemical_formula_weight         254.29
_exptl_crystal_colour_primary    yellow
_chemical_melting_point          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_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.
;

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

_cell_length_a                   10.6661(4)
_cell_length_b                   4.9190(2)
_cell_length_c                   23.7529(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.205(2)
_cell_angle_gamma                90
_cell_volume                     1218.06(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    5657
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      28.31
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6169
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1264 before and 0.0581 after correction.
The Ratio of minimum to maximum transmission is 0.8273.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.996
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            13236
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_theta_min         2.305
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3043
_reflns_number_gt                2490
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+0.7111P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3043
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1129
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_
_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 0.24775(10) 0.2150(2) 0.51158(4) 0.0196(2) Uani 1 1 d . . . . .
N1 N 0.17905(11) 0.6495(2) 0.49854(5) 0.0147(2) Uani 1 1 d . . . . .
H1 H 0.183865 0.816868 0.511941 0.018 Uiso 1 1 calc R U . . .
N2 N 0.28556(11) 0.7303(2) 0.61251(5) 0.0153(2) Uani 1 1 d . . . . .
N3 N 0.47825(11) 0.7144(2) 0.68608(5) 0.0142(2) Uani 1 1 d . . . . .
N4 N 0.53422(11) 0.8316(2) 0.73693(5) 0.0162(3) Uani 1 1 d . . . . .
C1 C 0.01900(14) 0.8359(3) 0.41819(6) 0.0196(3) Uani 1 1 d . . . . .
H1A H -0.037046 0.788925 0.381205 0.029 Uiso 1 1 calc R U . . .
H1B H 0.079660 0.977145 0.412192 0.029 Uiso 1 1 calc R U . . .
H1C H -0.033058 0.903543 0.444614 0.029 Uiso 1 1 calc R U . . .
C2 C 0.09228(13) 0.5860(3) 0.44374(6) 0.0155(3) Uani 1 1 d . . . . .
H2A H 0.030952 0.443681 0.449934 0.019 Uiso 1 1 calc R U . . .
H2B H 0.142391 0.513880 0.416399 0.019 Uiso 1 1 calc R U . . .
C3 C 0.25073(12) 0.4547(3) 0.52817(6) 0.0139(3) Uani 1 1 d . . . . .
C4 C 0.33542(12) 0.5444(3) 0.58444(6) 0.0139(3) Uani 1 1 d . . . . .
C5 C 0.46132(12) 0.4257(3) 0.60458(6) 0.0142(3) Uani 1 1 d . . . . .
C6 C 0.51681(14) 0.2255(3) 0.57464(6) 0.0175(3) Uani 1 1 d . . . . .
H6 H 0.471076 0.162617 0.538243 0.021 Uiso 1 1 calc R U . . .
C7 C 0.63658(14) 0.1207(3) 0.59775(6) 0.0195(3) Uani 1 1 d . . . . .
H7 H 0.672386 -0.015423 0.577515 0.023 Uiso 1 1 calc R U . . .
C8 C 0.70560(13) 0.2149(3) 0.65112(6) 0.0192(3) Uani 1 1 d . . . . .
H8 H 0.787790 0.140554 0.666746 0.023 Uiso 1 1 calc R U . . .
C9 C 0.65651(13) 0.4130(3) 0.68128(6) 0.0174(3) Uani 1 1 d . . . . .
H9 H 0.704400 0.477647 0.717111 0.021 Uiso 1 1 calc R U . . .
C10 C 0.53425(12) 0.5171(3) 0.65792(5) 0.0145(3) Uani 1 1 d . . . . .
C11 C 0.35750(12) 0.8185(3) 0.66391(6) 0.0146(3) Uani 1 1 d . . . . .
C12 C 0.33515(13) 1.0123(3) 0.70290(6) 0.0166(3) Uani 1 1 d . . . . .
H12 H 0.260583 1.120880 0.700569 0.020 Uiso 1 1 calc R U . . .
C13 C 0.44667(13) 1.0133(3) 0.74666(6) 0.0153(3) Uani 1 1 d . . . . .
C14 C 0.47778(14) 1.1907(3) 0.79882(6) 0.0190(3) Uani 1 1 d . . . . .
H14A H 0.563850 1.146885 0.820875 0.028 Uiso 1 1 calc R U . . .
H14B H 0.414929 1.159898 0.822863 0.028 Uiso 1 1 calc R U . . .
H14C H 0.474965 1.381813 0.786933 0.028 Uiso 1 1 calc R U . . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.2415(17) . ?
N1 H1 0.8800 . ?
N1 C2 1.4627(16) . ?
N1 C3 1.3308(17) . ?
N2 C4 1.3090(17) . ?
N2 C11 1.3680(17) . ?
N3 N4 1.3574(15) . ?
N3 C10 1.3839(17) . ?
N3 C11 1.3826(17) . ?
N4 C13 1.3476(18) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.5134(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5122(18) . ?
C4 C5 1.4496(18) . ?
C5 C6 1.4156(19) . ?
C5 C10 1.4127(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.379(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.403(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.377(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.4017(19) . ?
C11 C12 1.3843(19) . ?
C12 H12 0.9500 . ?
C12 C13 1.4045(19) . ?
C13 C14 1.4942(19) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C2 N1 H1 120.0 . . ?
C3 N1 H1 120.0 . . ?
C3 N1 C2 120.09(11) . . ?
C4 N2 C11 117.68(11) . . ?
N4 N3 C10 125.06(11) . . ?
N4 N3 C11 112.38(11) . . ?
C11 N3 C10 122.55(11) . . ?
C13 N4 N3 104.12(11) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C2 C1 111.05(11) . . ?
N1 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
O1 C3 N1 122.89(12) . . ?
O1 C3 C4 121.87(12) . . ?
N1 C3 C4 115.23(12) . . ?
N2 C4 C3 115.02(11) . . ?
N2 C4 C5 124.13(12) . . ?
C5 C4 C3 120.84(12) . . ?
C6 C5 C4 124.82(12) . . ?
C10 C5 C4 117.63(12) . . ?
C10 C5 C6 117.55(12) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.70(13) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.06(13) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.29(13) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 120.8 . . ?
C8 C9 C10 118.48(13) . . ?
C10 C9 H9 120.8 . . ?
N3 C10 C5 116.40(12) . . ?
N3 C10 C9 121.68(12) . . ?
C9 C10 C5 121.91(13) . . ?
N2 C11 N3 121.60(12) . . ?
N2 C11 C12 132.23(12) . . ?
N3 C11 C12 106.17(11) . . ?
C11 C12 H12 127.5 . . ?
C11 C12 C13 105.02(12) . . ?
C13 C12 H12 127.5 . . ?
N4 C13 C12 112.31(12) . . ?
N4 C13 C14 119.29(12) . . ?
C12 C13 C14 128.37(13) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.88 2.07 2.8762(15) 151.1 1_565 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C4 N2 -143.17(13) . . . . ?
O1 C3 C4 C5 36.14(19) . . . . ?
N1 C3 C4 N2 35.90(17) . . . . ?
N1 C3 C4 C5 -144.80(12) . . . . ?
N2 C4 C5 C6 -179.70(13) . . . . ?
N2 C4 C5 C10 0.1(2) . . . . ?
N2 C11 C12 C13 -178.71(14) . . . . ?
N3 N4 C13 C12 0.44(15) . . . . ?
N3 N4 C13 C14 -177.80(11) . . . . ?
N3 C11 C12 C13 0.43(15) . . . . ?
N4 N3 C10 C5 -178.43(12) . . . . ?
N4 N3 C10 C9 1.9(2) . . . . ?
N4 N3 C11 N2 179.07(12) . . . . ?
N4 N3 C11 C12 -0.19(15) . . . . ?
C2 N1 C3 O1 -0.3(2) . . . . ?
C2 N1 C3 C4 -179.33(11) . . . . ?
C3 N1 C2 C1 179.04(12) . . . . ?
C3 C4 C5 C6 1.1(2) . . . . ?
C3 C4 C5 C10 -179.17(12) . . . . ?
C4 N2 C11 N3 -0.60(19) . . . . ?
C4 N2 C11 C12 178.43(14) . . . . ?
C4 C5 C6 C7 -178.82(13) . . . . ?
C4 C5 C10 N3 -0.29(18) . . . . ?
C4 C5 C10 C9 179.41(12) . . . . ?
C5 C6 C7 C8 -0.9(2) . . . . ?
C6 C5 C10 N3 179.49(12) . . . . ?
C6 C5 C10 C9 -0.8(2) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
C7 C8 C9 C10 1.0(2) . . . . ?
C8 C9 C10 N3 179.32(13) . . . . ?
C8 C9 C10 C5 -0.4(2) . . . . ?
C10 N3 N4 C13 178.50(12) . . . . ?
C10 N3 C11 N2 0.4(2) . . . . ?
C10 N3 C11 C12 -178.88(12) . . . . ?
C10 C5 C6 C7 1.4(2) . . . . ?
C11 N2 C4 C3 179.66(11) . . . . ?
C11 N2 C4 C5 0.4(2) . . . . ?
C11 N3 N4 C13 -0.15(15) . . . . ?
C11 N3 C10 C5 0.09(18) . . . . ?
C11 N3 C10 C9 -179.62(12) . . . . ?
C11 C12 C13 N4 -0.56(16) . . . . ?
C11 C12 C13 C14 177.48(13) . . . . ?

