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

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

data_11
_database_code_depnum_ccdc_archive 'CCDC 2251361'
loop_
_audit_author_name
_audit_author_address
'jing zhang'
;Guangzhou University of Chinese Medicine
China
;
_audit_update_record             
;
2023-03-24 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_audit_creation_date             2022-05-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H11 N3 O2'
_chemical_formula_sum            'C11 H11 N3 O2'
_chemical_formula_weight         217.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.7766(8)
_cell_length_b                   9.6982(9)
_cell_length_c                   13.2431(13)
_cell_angle_alpha                99.818(4)
_cell_angle_beta                 98.950(4)
_cell_angle_gamma                101.433(4)
_cell_volume                     1067.53(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7696
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      60.596
_cell_measurement_theta_min      5.600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1148 before and 0.0628 after correction.
The Ratio of minimum to maximum transmission is 0.7564.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.15
_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  0.0493
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14132
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         2.190
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1997996
_diffrn_source_voltage           69.86
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3797
_reflns_number_total             4746
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4746
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.076
_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)+(0.0528P)²+0.2928P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1217
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N4(H4), C11(H11), C18(H18), C7(H7), C22(H22), C21(H21), C8(H8),
 C9(H9), C20(H20), C19(H19), C10(H10)
2.c X=CH2 refined with riding coordinates:
 N5(H5A,H5B), N2(H2A,H2B)
2.d :
 C1(H1A), C12(H12)
;
_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
O2 O 0.87106(11) 0.14248(10) 0.34839(7) 0.0221(2) Uani 1 1 d . . . . .
O4 O 0.36914(12) 0.33233(10) 0.34279(7) 0.0245(2) Uani 1 1 d . . . . .
O3 O 0.31822(12) 0.11593(10) 0.38721(8) 0.0267(2) Uani 1 1 d . . . . .
O1 O 0.81569(12) 0.35925(10) 0.39275(8) 0.0263(2) Uani 1 1 d . . . . .
N3 N 0.74367(13) 0.17181(11) 0.47953(8) 0.0203(2) Uani 1 1 d . . . . .
N1 N 0.62145(14) 0.17413(12) 0.61836(9) 0.0212(2) Uani 1 1 d . . . . .
H1 H 0.609840 0.080245 0.602937 0.025 Uiso 1 1 calc R U . . .
N6 N 0.24928(13) 0.31775(11) 0.47672(8) 0.0212(2) Uani 1 1 d . . . . .
N5 N 0.18312(14) 0.11786(12) 0.55630(9) 0.0238(3) Uani 1 1 d . . . . .
H5A H 0.222702 0.062292 0.512742 0.029 Uiso 1 1 calc R U . . .
H5B H 0.140379 0.083850 0.605501 0.029 Uiso 1 1 calc R U . . .
N4 N 0.12895(14) 0.33882(12) 0.61551(9) 0.0239(3) Uani 1 1 d . . . . .
H4 H 0.119416 0.421195 0.598891 0.029 Uiso 1 1 calc R U . . .
N2 N 0.66231(15) 0.38081(12) 0.55197(9) 0.0269(3) Uani 1 1 d . . . . .
H2A H 0.696548 0.428631 0.505977 0.032 Uiso 1 1 calc R U . . .
H2B H 0.617571 0.421783 0.600261 0.032 Uiso 1 1 calc R U . . .
C15 C 0.31025(16) 0.24275(14) 0.40453(10) 0.0201(3) Uani 1 1 d . . . . .
C4 C 0.80770(15) 0.23740(13) 0.40925(10) 0.0188(3) Uani 1 1 d . . . . .
C16 C 0.18786(15) 0.25236(14) 0.54782(10) 0.0195(3) Uani 1 1 d . . . . .
C5 C 0.67812(16) 0.24726(14) 0.54852(10) 0.0200(3) Uani 1 1 d . . . . .
C6 C 0.57851(15) 0.22983(14) 0.71313(10) 0.0194(3) Uani 1 1 d . . . . .
C17 C 0.08065(16) 0.31471(14) 0.70935(10) 0.0204(3) Uani 1 1 d . . . . .
C3 C 0.94395(17) 0.19684(15) 0.26827(11) 0.0239(3) Uani 1 1 d . . . . .
H3A H 1.023564 0.142070 0.250698 0.029 Uiso 1 1 calc R U . . .
H3B H 0.999740 0.298915 0.295256 0.029 Uiso 1 1 calc R U . . .
C11 C 0.46780(17) 0.13845(15) 0.75061(11) 0.0247(3) Uani 1 1 d . . . . .
H11 H 0.421181 0.043766 0.711418 0.030 Uiso 1 1 calc R U . . .
C14 C 0.44331(17) 0.27018(16) 0.26236(11) 0.0260(3) Uani 1 1 d . . . . .
H14A H 0.494554 0.196426 0.286824 0.031 Uiso 1 1 calc R U . . .
H14B H 0.526837 0.345971 0.249005 0.031 Uiso 1 1 calc R U . . .
C18 C 0.12804(17) 0.42873(15) 0.79532(11) 0.0269(3) Uani 1 1 d . . . . .
H18 H 0.191221 0.517509 0.789367 0.032 Uiso 1 1 calc R U . . .
C7 C 0.64924(17) 0.36720(15) 0.77250(11) 0.0248(3) Uani 1 1 d . . . . .
H7 H 0.727954 0.429193 0.748929 0.030 Uiso 1 1 calc R U . . .
C2 C 0.82685(18) 0.18527(15) 0.17367(11) 0.0270(3) Uani 1 1 d . . . . .
C13 C 0.32900(18) 0.20419(15) 0.16505(11) 0.0276(3) Uani 1 1 d . . . . .
C22 C -0.01471(16) 0.18589(15) 0.71793(11) 0.0240(3) Uani 1 1 d . . . . .
H22 H -0.050416 0.108294 0.659081 0.029 Uiso 1 1 calc R U . . .
C21 C -0.05736(18) 0.17132(16) 0.81277(12) 0.0301(3) Uani 1 1 d . . . . .
H21 H -0.121226 0.082917 0.818815 0.036 Uiso 1 1 calc R U . . .
C8 C 0.60435(19) 0.41317(16) 0.86613(11) 0.0295(3) Uani 1 1 d . . . . .
H8 H 0.651323 0.507475 0.905896 0.035 Uiso 1 1 calc R U . . .
C9 C 0.4920(2) 0.32311(17) 0.90212(12) 0.0323(3) Uani 1 1 d . . . . .
H9 H 0.460700 0.355756 0.965799 0.039 Uiso 1 1 calc R U . . .
C20 C -0.0080(2) 0.28396(18) 0.89850(12) 0.0340(4) Uani 1 1 d . . . . .
H20 H -0.036640 0.272716 0.963404 0.041 Uiso 1 1 calc R U . . .
C19 C 0.08397(19) 0.41398(17) 0.88937(12) 0.0321(3) Uani 1 1 d . . . . .
H19 H 0.116422 0.492506 0.947685 0.038 Uiso 1 1 calc R U . . .
C1 C 0.7335(2) 0.17456(18) 0.09597(13) 0.0392(4) Uani 1 1 d . . . . .
H1A H 0.658796 0.165987 0.033766 0.047 Uiso 1 1 calc R U . . .
C10 C 0.42520(19) 0.18478(17) 0.84472(12) 0.0316(3) Uani 1 1 d . . . . .
H10 H 0.349973 0.121627 0.870071 0.038 Uiso 1 1 calc R U . . .
C12 C 0.2399(2) 0.15222(19) 0.08463(13) 0.0403(4) Uani 1 1 d . . . . .
H12 H 0.168367 0.110512 0.020090 0.048 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
O2 C4 1.3769(16) . ?
O2 C3 1.4426(16) . ?
O4 C15 1.3734(16) . ?
O4 C14 1.4401(16) . ?
O3 C15 1.2301(16) . ?
O1 C4 1.2285(16) . ?
N3 C4 1.3451(17) . ?
N3 C5 1.3430(17) . ?
N1 H1 0.8800 . ?
N1 C5 1.3538(17) . ?
N1 C6 1.4163(17) . ?
N6 C15 1.3438(17) . ?
N6 C16 1.3436(17) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C16 1.3213(17) . ?
N4 H4 0.8800 . ?
N4 C16 1.3542(17) . ?
N4 C17 1.4150(17) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C5 1.3236(17) . ?
C6 C11 1.3909(19) . ?
C6 C7 1.3933(19) . ?
C17 C18 1.390(2) . ?
C17 C22 1.3920(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.464(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.384(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.462(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(2) . ?
C2 C1 1.187(2) . ?
C13 C12 1.184(2) . ?
C22 H22 0.9500 . ?
C22 C21 1.387(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.381(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.382(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.387(2) . ?
C20 H20 0.9500 . ?
C20 C19 1.391(2) . ?
C19 H19 0.9500 . ?
C1 H1A 0.9500 . ?
C10 H10 0.9500 . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O2 C3 115.73(10) . . ?
C15 O4 C14 116.28(10) . . ?
C5 N3 C4 118.55(11) . . ?
C5 N1 H1 115.9 . . ?
C5 N1 C6 128.11(11) . . ?
C6 N1 H1 115.9 . . ?
C16 N6 C15 119.28(11) . . ?
H5A N5 H5B 120.0 . . ?
C16 N5 H5A 120.0 . . ?
C16 N5 H5B 120.0 . . ?
C16 N4 H4 115.6 . . ?
C16 N4 C17 128.80(11) . . ?
C17 N4 H4 115.6 . . ?
H2A N2 H2B 120.0 . . ?
C5 N2 H2A 120.0 . . ?
C5 N2 H2B 120.0 . . ?
O3 C15 O4 119.86(12) . . ?
O3 C15 N6 131.36(12) . . ?
N6 C15 O4 108.77(11) . . ?
O1 C4 O2 119.55(12) . . ?
O1 C4 N3 131.48(13) . . ?
N3 C4 O2 108.97(11) . . ?
N6 C16 N4 113.62(11) . . ?
N5 C16 N6 126.17(13) . . ?
N5 C16 N4 120.21(12) . . ?
N3 C5 N1 114.43(11) . . ?
N2 C5 N3 126.35(12) . . ?
N2 C5 N1 119.21(12) . . ?
C11 C6 N1 117.55(12) . . ?
C11 C6 C7 119.39(13) . . ?
C7 C6 N1 122.93(12) . . ?
C18 C17 N4 117.15(12) . . ?
C18 C17 C22 119.45(13) . . ?
C22 C17 N4 123.36(12) . . ?
O2 C3 H3A 109.3 . . ?
O2 C3 H3B 109.3 . . ?
O2 C3 C2 111.71(11) . . ?
H3A C3 H3B 107.9 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C6 C11 H11 119.8 . . ?
C10 C11 C6 120.33(13) . . ?
C10 C11 H11 119.8 . . ?
O4 C14 H14A 109.2 . . ?
O4 C14 H14B 109.2 . . ?
O4 C14 C13 111.84(12) . . ?
H14A C14 H14B 107.9 . . ?
C13 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.54(14) . . ?
C19 C18 H18 119.7 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.79(13) . . ?
C8 C7 H7 120.1 . . ?
C1 C2 C3 178.80(17) . . ?
C12 C13 C14 177.99(16) . . ?
C17 C22 H22 120.1 . . ?
C21 C22 C17 119.72(13) . . ?
C21 C22 H22 120.1 . . ?
C22 C21 H21 119.7 . . ?
C20 C21 C22 120.69(14) . . ?
C20 C21 H21 119.7 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.64(14) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.61(14) . . ?
C10 C9 H9 120.2 . . ?
C21 C20 H20 120.2 . . ?
C21 C20 C19 119.68(14) . . ?
C19 C20 H20 120.2 . . ?
C18 C19 C20 119.89(14) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C2 C1 H1A 180.0 . . ?
C11 C10 C9 120.19(14) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C13 C12 H12 180.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C6 C11 C10 177.65(13) . . . . ?
N1 C6 C7 C8 -178.16(13) . . . . ?
N4 C17 C18 C19 179.25(13) . . . . ?
N4 C17 C22 C21 -179.68(13) . . . . ?
C15 O4 C14 C13 88.78(14) . . . . ?
C15 N6 C16 N5 1.4(2) . . . . ?
C15 N6 C16 N4 -179.40(11) . . . . ?
C4 O2 C3 C2 -83.54(14) . . . . ?
C4 N3 C5 N1 -177.91(11) . . . . ?
C4 N3 C5 N2 3.6(2) . . . . ?
C16 N6 C15 O4 -178.43(11) . . . . ?
C16 N6 C15 O3 2.4(2) . . . . ?
C16 N4 C17 C18 136.08(14) . . . . ?
C16 N4 C17 C22 -46.1(2) . . . . ?
C5 N3 C4 O2 178.55(10) . . . . ?
C5 N3 C4 O1 -2.1(2) . . . . ?
C5 N1 C6 C11 154.68(13) . . . . ?
C5 N1 C6 C7 -29.5(2) . . . . ?
C6 N1 C5 N3 164.77(12) . . . . ?
C6 N1 C5 N2 -16.6(2) . . . . ?
C6 C11 C10 C9 0.4(2) . . . . ?
C6 C7 C8 C9 1.1(2) . . . . ?
C17 N4 C16 N6 -168.33(12) . . . . ?
C17 N4 C16 N5 10.9(2) . . . . ?
C17 C18 C19 C20 0.3(2) . . . . ?
C17 C22 C21 C20 0.9(2) . . . . ?
C3 O2 C4 O1 0.19(17) . . . . ?
C3 O2 C4 N3 179.67(10) . . . . ?
C11 C6 C7 C8 -2.4(2) . . . . ?
C14 O4 C15 O3 -2.28(18) . . . . ?
C14 O4 C15 N6 178.40(10) . . . . ?
C18 C17 C22 C21 -1.9(2) . . . . ?
C7 C6 C11 C10 1.7(2) . . . . ?
C7 C8 C9 C10 0.9(2) . . . . ?
C22 C17 C18 C19 1.4(2) . . . . ?
C22 C21 C20 C19 0.8(2) . . . . ?
C21 C20 C19 C18 -1.3(2) . . . . ?
C8 C9 C10 C11 -1.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2251362'
loop_
_audit_author_name
_audit_author_address
'jing zhang'
;Guangzhou University of Chinese Medicine
China
;
_audit_update_record             
;
2023-03-24 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_audit_creation_date             2022-04-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H8 Cl3 N3 O2'
_chemical_formula_sum            'C11 H8 Cl3 N3 O2'
_chemical_formula_weight         320.55
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

_cell_length_a                   7.5748(3)
_cell_length_b                   12.5331(4)
_cell_length_c                   13.9255(5)
_cell_angle_alpha                91.8130(10)
_cell_angle_beta                 97.6170(10)
_cell_angle_gamma                102.8260(10)
_cell_volume                     1275.11(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9793
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      68.728
_cell_measurement_theta_min      3.152
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.3899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1415 before and 0.0857 after correction.
The Ratio of minimum to maximum transmission is 0.5177.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20912
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.605
_diffrn_reflns_theta_min         1.478
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.19985679999999997
_diffrn_source_voltage           69.88
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6291
_reflns_number_total             6864
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         6864
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0617P)²+0.8554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1177
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C22(H22), C11(H11), C18(H18)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N5(H5A,H5B), C15(H15A,H15B), C4(H4A,H4B)
;
_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
Cl2 Cl 0.82903(6) 1.02594(3) 0.12531(3) 0.03224(11) Uani 1 1 d . . . . .
Cl5 Cl 0.65633(6) 0.25601(3) 0.73311(3) 0.03134(11) Uani 1 1 d . . . . .
Cl6 Cl 0.68663(6) 0.09494(4) 0.56237(3) 0.03296(11) Uani 1 1 d . . . . .
Cl3 Cl 0.84136(7) 0.78121(4) 0.07261(3) 0.03634(12) Uani 1 1 d . . . . .
Cl4 Cl 0.63995(7) 0.16924(4) 0.94215(3) 0.03566(12) Uani 1 1 d . . . . .
Cl1 Cl 0.84799(7) 1.10156(3) 0.34352(3) 0.03370(11) Uani 1 1 d . . . . .
O2 O 0.74576(17) 0.48535(10) 0.67012(9) 0.0282(3) Uani 1 1 d . . . . .
O3 O 0.30297(18) -0.47543(11) 0.84385(12) 0.0395(3) Uani 1 1 d . . . . .
O1 O 0.50964(18) 0.55281(12) 0.61024(11) 0.0369(3) Uani 1 1 d . . . . .
O4 O 0.5409(2) -0.54690(11) 0.89442(12) 0.0386(3) Uani 1 1 d . . . . .
N3 N 0.79833(17) 0.61387(11) 0.56332(10) 0.0214(2) Uani 1 1 d . . . . .
N1 N 0.87094(19) 0.70854(11) 0.43005(10) 0.0248(3) Uani 1 1 d . . . . .
N6 N 0.60378(19) -0.37476(11) 0.85003(10) 0.0229(3) Uani 1 1 d . . . . .
N2 N 0.6027(2) 0.72097(14) 0.49554(12) 0.0320(3) Uani 1 1 d . . . . .
H2A H 0.570804 0.766845 0.453682 0.038 Uiso 1 1 calc R U . . .
H2B H 0.534373 0.698691 0.540687 0.038 Uiso 1 1 calc R U . . .
N4 N 0.7093(2) -0.20025(12) 0.80451(13) 0.0309(3) Uani 1 1 d . . . . .
N5 N 0.3987(2) -0.26029(13) 0.82063(15) 0.0398(4) Uani 1 1 d . . . . .
H5A H 0.371041 -0.197553 0.806197 0.048 Uiso 1 1 calc R U . . .
H5B H 0.313287 -0.315543 0.834090 0.048 Uiso 1 1 calc R U . . .
C7 C 0.6711(2) -0.02303(14) 0.86312(13) 0.0278(3) Uani 1 1 d . . . . .
H7 H 0.667864 -0.048215 0.926629 0.033 Uiso 1 1 calc R U . . .
C22 C 0.8436(2) 0.75060(13) 0.26236(12) 0.0248(3) Uani 1 1 d . . . . .
H22 H 0.845086 0.676869 0.245202 0.030 Uiso 1 1 calc R U . . .
C13 C 0.6685(2) 0.55154(13) 0.61341(12) 0.0243(3) Uani 1 1 d . . . . .
C20 C 0.8355(2) 0.93371(13) 0.21382(11) 0.0236(3) Uani 1 1 d . . . . .
C16 C 0.7571(2) 0.68463(12) 0.49049(11) 0.0210(3) Uani 1 1 d . . . . .
C5 C 0.5718(2) -0.27177(12) 0.82212(12) 0.0227(3) Uani 1 1 d . . . . .
C21 C 0.8379(2) 0.82490(13) 0.19095(12) 0.0243(3) Uani 1 1 d . . . . .
C10 C 0.6796(2) 0.05100(13) 0.67842(12) 0.0246(3) Uani 1 1 d . . . . .
C6 C 0.6864(2) -0.09375(13) 0.78700(13) 0.0257(3) Uani 1 1 d . . . . .
C19 C 0.8403(2) 0.96578(13) 0.31070(12) 0.0236(3) Uani 1 1 d . . . . .
C17 C 0.8471(2) 0.78371(13) 0.35919(12) 0.0228(3) Uani 1 1 d . . . . .
C14 C 0.9729(2) 0.59252(13) 0.59304(11) 0.0216(3) Uani 1 1 d . . . . .
C8 C 0.6608(2) 0.08385(13) 0.84644(12) 0.0258(3) Uani 1 1 d . . . . .
C9 C 0.6658(2) 0.12265(12) 0.75392(12) 0.0239(3) Uani 1 1 d . . . . .
C3 C 0.7787(2) -0.39728(13) 0.87684(12) 0.0239(3) Uani 1 1 d . . . . .
C15 C 1.1351(2) 0.64156(15) 0.57173(14) 0.0307(3) Uani 1 1 d . . . . .
H15A H 1.145788 0.700889 0.530454 0.037 Uiso 1 1 calc R U . . .
H15B H 1.240975 0.617454 0.597680 0.037 Uiso 1 1 calc R U . . .
C11 C 0.6907(2) -0.05630(13) 0.69399(13) 0.0268(3) Uani 1 1 d . . . . .
H11 H 0.701204 -0.103858 0.641612 0.032 Uiso 1 1 calc R U . . .
C18 C 0.8452(2) 0.89260(13) 0.38330(12) 0.0248(3) Uani 1 1 d . . . . .
H18 H 0.847230 0.916362 0.448980 0.030 Uiso 1 1 calc R U . . .
C4 C 0.9443(2) -0.33691(15) 0.87504(15) 0.0330(4) Uani 1 1 d . . . . .
H4A H 0.959690 -0.264992 0.852814 0.040 Uiso 1 1 calc R U . . .
H4B H 1.048307 -0.365289 0.895977 0.040 Uiso 1 1 calc R U . . .
C2 C 0.4664(2) -0.46594(14) 0.86076(14) 0.0294(3) Uani 1 1 d . . . . .
C12 C 0.9370(2) 0.50027(14) 0.65928(13) 0.0274(3) Uani 1 1 d . . . . .
H12A H 0.960823 0.432619 0.630261 0.033 Uiso 1 1 calc R U . . .
H12B H 1.015558 0.519609 0.722901 0.033 Uiso 1 1 calc R U . . .
C1 C 0.7369(3) -0.51119(15) 0.91211(15) 0.0336(4) Uani 1 1 d . . . . .
H1A H 0.794352 -0.560355 0.875941 0.040 Uiso 1 1 calc R U . . .
H1B H 0.782526 -0.510302 0.982188 0.040 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
Cl2 C20 1.7196(16) . ?
Cl5 C9 1.7208(16) . ?
Cl6 C10 1.7274(17) . ?
Cl3 C21 1.7253(16) . ?
Cl4 C8 1.7283(18) . ?
Cl1 C19 1.7343(16) . ?
O2 C13 1.3373(19) . ?
O2 C12 1.448(2) . ?
O3 C2 1.207(2) . ?
O1 C13 1.202(2) . ?
O4 C2 1.335(2) . ?
O4 C1 1.438(2) . ?
N3 C13 1.392(2) . ?
N3 C16 1.4173(19) . ?
N3 C14 1.4181(19) . ?
N1 C16 1.279(2) . ?
N1 C17 1.407(2) . ?
N6 C5 1.422(2) . ?
N6 C3 1.420(2) . ?
N6 C2 1.391(2) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C16 1.355(2) . ?
N4 C5 1.271(2) . ?
N4 C6 1.408(2) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C5 1.348(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.393(2) . ?
C7 C8 1.384(2) . ?
C22 H22 0.9500 . ?
C22 C21 1.387(2) . ?
C22 C17 1.393(2) . ?
C20 C21 1.395(2) . ?
C20 C19 1.389(2) . ?
C10 C9 1.391(2) . ?
C10 C11 1.388(2) . ?
C6 C11 1.394(2) . ?
C19 C18 1.389(2) . ?
C17 C18 1.399(2) . ?
C14 C15 1.322(2) . ?
C14 C12 1.502(2) . ?
C8 C9 1.394(2) . ?
C3 C4 1.317(2) . ?
C3 C1 1.505(2) . ?
C15 H15A 0.9500 . ?
C15 H15B 0.9500 . ?
C11 H11 0.9500 . ?
C18 H18 0.9500 . ?
C4 H4A 0.9500 . ?
C4 H4B 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O2 C12 110.15(13) . . ?
C2 O4 C1 110.37(14) . . ?
C13 N3 C16 123.94(13) . . ?
C13 N3 C14 110.26(13) . . ?
C14 N3 C16 125.75(13) . . ?
C16 N1 C17 120.59(14) . . ?
C3 N6 C5 125.20(13) . . ?
C2 N6 C5 124.26(14) . . ?
C2 N6 C3 110.42(13) . . ?
H2A N2 H2B 120.0 . . ?
C16 N2 H2A 120.0 . . ?
C16 N2 H2B 120.0 . . ?
C5 N4 C6 118.22(14) . . ?
H5A N5 H5B 120.0 . . ?
C5 N5 H5A 120.0 . . ?
C5 N5 H5B 120.0 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C8 C7 C6 120.17(16) . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C17 120.23(15) . . ?
C17 C22 H22 119.9 . . ?
O2 C13 N3 109.81(13) . . ?
O1 C13 O2 121.83(15) . . ?
O1 C13 N3 128.36(15) . . ?
C21 C20 Cl2 121.25(12) . . ?
C19 C20 Cl2 120.82(12) . . ?
C19 C20 C21 117.92(14) . . ?
N1 C16 N3 116.74(13) . . ?
N1 C16 N2 128.03(15) . . ?
N2 C16 N3 115.20(14) . . ?
N4 C5 N6 116.86(14) . . ?
N4 C5 N5 127.46(15) . . ?
N5 C5 N6 115.63(14) . . ?
C22 C21 Cl3 118.52(13) . . ?
C22 C21 C20 121.24(15) . . ?
C20 C21 Cl3 120.20(12) . . ?
C9 C10 Cl6 120.26(12) . . ?
C11 C10 Cl6 118.30(13) . . ?
C11 C10 C9 121.44(15) . . ?
C7 C6 N4 120.50(16) . . ?
C11 C6 N4 119.77(16) . . ?
C11 C6 C7 119.60(15) . . ?
C20 C19 Cl1 119.68(12) . . ?
C20 C19 C18 121.77(15) . . ?
C18 C19 Cl1 118.52(13) . . ?
C22 C17 N1 118.14(14) . . ?
C22 C17 C18 119.20(14) . . ?
C18 C17 N1 122.35(15) . . ?
N3 C14 C12 104.44(13) . . ?
C15 C14 N3 129.96(15) . . ?
C15 C14 C12 125.58(15) . . ?
C7 C8 Cl4 119.07(13) . . ?
C7 C8 C9 120.91(16) . . ?
C9 C8 Cl4 120.02(13) . . ?
C10 C9 Cl5 120.52(12) . . ?
C10 C9 C8 118.37(14) . . ?
C8 C9 Cl5 121.11(13) . . ?
N6 C3 C1 104.02(14) . . ?
C4 C3 N6 131.05(16) . . ?
C4 C3 C1 124.92(16) . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C10 C11 C6 119.52(16) . . ?
C10 C11 H11 120.2 . . ?
C6 C11 H11 120.2 . . ?
C19 C18 C17 119.64(15) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C3 C4 H4A 120.0 . . ?
C3 C4 H4B 120.0 . . ?
H4A C4 H4B 120.0 . . ?
O3 C2 O4 122.38(16) . . ?
O3 C2 N6 127.89(16) . . ?
O4 C2 N6 109.73(15) . . ?
O2 C12 C14 104.91(12) . . ?
O2 C12 H12A 110.8 . . ?
O2 C12 H12B 110.8 . . ?
C14 C12 H12A 110.8 . . ?
C14 C12 H12B 110.8 . . ?
H12A C12 H12B 108.8 . . ?
O4 C1 C3 105.22(14) . . ?
O4 C1 H1A 110.7 . . ?
O4 C1 H1B 110.7 . . ?
C3 C1 H1A 110.7 . . ?
C3 C1 H1B 110.7 . . ?
H1A C1 H1B 108.8 . . ?

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
Cl2 C20 C21 Cl3 1.9(2) . . . . ?
Cl2 C20 C21 C22 179.85(13) . . . . ?
Cl2 C20 C19 Cl1 -2.3(2) . . . . ?
Cl2 C20 C19 C18 179.86(13) . . . . ?
Cl6 C10 C9 Cl5 -0.2(2) . . . . ?
Cl6 C10 C9 C8 -179.91(13) . . . . ?
Cl6 C10 C11 C6 179.63(13) . . . . ?
Cl4 C8 C9 Cl5 1.4(2) . . . . ?
Cl4 C8 C9 C10 -178.94(12) . . . . ?
Cl1 C19 C18 C17 -177.27(13) . . . . ?
N3 C14 C12 O2 -6.31(17) . . . . ?
N1 C17 C18 C19 173.31(15) . . . . ?
N6 C3 C1 O4 4.73(19) . . . . ?
N4 C6 C11 C10 -175.97(15) . . . . ?
C7 C6 C11 C10 -0.1(2) . . . . ?
C7 C8 C9 Cl5 -179.04(13) . . . . ?
C7 C8 C9 C10 0.7(2) . . . . ?
C22 C17 C18 C19 -0.2(2) . . . . ?
C13 O2 C12 C14 4.39(18) . . . . ?
C13 N3 C16 N1 -158.05(16) . . . . ?
C13 N3 C16 N2 23.6(2) . . . . ?
C13 N3 C14 C15 -172.19(18) . . . . ?
C13 N3 C14 C12 6.26(17) . . . . ?
C20 C19 C18 C17 0.6(3) . . . . ?
C16 N3 C13 O2 173.87(14) . . . . ?
C16 N3 C13 O1 -6.4(3) . . . . ?
C16 N3 C14 C15 10.2(3) . . . . ?
C16 N3 C14 C12 -171.34(14) . . . . ?
C16 N1 C17 C22 -125.95(17) . . . . ?
C16 N1 C17 C18 60.5(2) . . . . ?
C5 N6 C3 C4 -6.3(3) . . . . ?
C5 N6 C3 C1 172.68(15) . . . . ?
C5 N6 C2 O3 4.4(3) . . . . ?
C5 N6 C2 O4 -175.40(15) . . . . ?
C5 N4 C6 C7 74.2(2) . . . . ?
C5 N4 C6 C11 -109.9(2) . . . . ?
C21 C22 C17 N1 -173.87(15) . . . . ?
C21 C22 C17 C18 -0.1(2) . . . . ?
C21 C20 C19 Cl1 177.09(12) . . . . ?
C21 C20 C19 C18 -0.8(2) . . . . ?
C6 N4 C5 N6 -173.23(15) . . . . ?
C6 N4 C5 N5 4.3(3) . . . . ?
C6 C7 C8 Cl4 179.45(13) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C19 C20 C21 Cl3 -177.44(12) . . . . ?
C19 C20 C21 C22 0.5(2) . . . . ?
C17 N1 C16 N3 -175.92(14) . . . . ?
C17 N1 C16 N2 2.1(3) . . . . ?
C17 C22 C21 Cl3 177.90(13) . . . . ?
C17 C22 C21 C20 0.0(2) . . . . ?
C14 N3 C13 O2 -3.78(19) . . . . ?
C14 N3 C13 O1 175.93(18) . . . . ?
C14 N3 C16 N1 19.2(2) . . . . ?
C14 N3 C16 N2 -159.07(15) . . . . ?
C8 C7 C6 N4 175.73(16) . . . . ?
C8 C7 C6 C11 -0.1(3) . . . . ?
C9 C10 C11 C6 0.6(2) . . . . ?
C3 N6 C5 N4 12.2(2) . . . . ?
C3 N6 C5 N5 -165.65(16) . . . . ?
C3 N6 C2 O3 -179.39(19) . . . . ?
C3 N6 C2 O4 0.8(2) . . . . ?
C15 C14 C12 O2 172.24(16) . . . . ?
C11 C10 C9 Cl5 178.82(13) . . . . ?
C11 C10 C9 C8 -0.9(2) . . . . ?
C4 C3 C1 O4 -176.19(18) . . . . ?
C2 O4 C1 C3 -4.5(2) . . . . ?
C2 N6 C5 N4 -172.10(17) . . . . ?
C2 N6 C5 N5 10.0(2) . . . . ?
C2 N6 C3 C4 177.48(19) . . . . ?
C2 N6 C3 C1 -3.52(18) . . . . ?
C12 O2 C13 O1 179.66(17) . . . . ?
C12 O2 C13 N3 -0.60(19) . . . . ?
C1 O4 C2 O3 -177.33(19) . . . . ?
C1 O4 C2 N6 2.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2251364'
loop_
_audit_author_name
_audit_author_address
'jing zhang'
;Guangzhou University of Chinese Medicine
China
;
_audit_update_record             
;
2023-03-24 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_audit_creation_date             2022-05-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 I N3 O3'
_chemical_formula_sum            'C12 H12 I N3 O3'
_chemical_formula_weight         373.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.4737(4)
_cell_length_b                   7.2411(2)
_cell_length_c                   15.4718(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.0440(10)
_cell_angle_gamma                90
_cell_volume                     1343.03(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7561
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      60.594
_cell_measurement_theta_min      3.520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.392
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.3393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1554 before and 0.0869 after correction.
The Ratio of minimum to maximum transmission is 0.4513.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_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  0.0619
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9658
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         1.864
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.19977099999999998
_diffrn_source_voltage           69.85
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2469
_reflns_number_total             2930
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.425
_refine_diff_density_min         -2.416
_refine_diff_density_rms         0.248
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2930
_refine_ls_number_restraints     253
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0972P)²+2.0667P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1479
_refine_ls_wR_factor_ref         0.1549
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4.a Rotating group:
 N2(H2A,H2B)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C10(H10), C8(H8), C7(H7), C11(H11)
4.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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
I1 I 1.15169(3) 0.11913(4) 0.60994(2) 0.02021(19) Uani 1 1 d . . . . .
O3 O 1.0353(3) 0.6957(6) 0.6989(3) 0.0249(8) Uani 1 1 d . U . . .
O1 O 0.3610(3) 0.1392(5) 0.2801(3) 0.0215(8) Uani 1 1 d . U . . .
O2 O 0.8692(4) 0.8326(6) 0.6550(3) 0.0310(9) Uani 1 1 d . U . . .
N3 N 0.8997(3) 0.5457(6) 0.5977(3) 0.0152(7) Uani 1 1 d . U . . .
N1 N 0.7812(4) 0.3689(5) 0.4890(3) 0.0166(8) Uani 1 1 d . U . . .
N2 N 0.7084(4) 0.6148(6) 0.5575(3) 0.0232(10) Uani 1 1 d . U . . .
H2A H 0.643872 0.581129 0.521060 0.028 Uiso 1 1 d R U . . .
H2B H 0.706689 0.600900 0.613637 0.028 Uiso 1 1 d R U . . .
C5 C 0.7908(4) 0.5061(6) 0.5420(3) 0.0133(8) Uani 1 1 d . U . . .
C9 C 0.4631(4) 0.2061(7) 0.3293(3) 0.0157(8) Uani 1 1 d . U . . .
C1 C 1.0009(4) 0.2644(7) 0.5743(3) 0.0169(9) Uani 1 1 d . U . . .
H1 H 0.937616 0.213724 0.531887 0.020 Uiso 1 1 calc R U . . .
C2 C 0.9941(4) 0.4281(7) 0.6114(3) 0.0144(8) Uani 1 1 d . U . . .
C10 C 0.5061(5) 0.3757(6) 0.3140(4) 0.0180(10) Uani 1 1 d . U . . .
H10 H 0.464635 0.453445 0.267135 0.022 Uiso 1 1 calc R U . . .
C4 C 0.9284(5) 0.7041(7) 0.6506(4) 0.0208(9) Uani 1 1 d . U . . .
C8 C 0.5256(5) 0.0907(7) 0.3967(4) 0.0193(10) Uani 1 1 d . U . . .
H8 H 0.497528 -0.027231 0.406303 0.023 Uiso 1 1 calc R U . . .
C6 C 0.6723(4) 0.3195(7) 0.4358(3) 0.0157(8) Uani 1 1 d . U . . .
C7 C 0.6291(4) 0.1485(7) 0.4498(4) 0.0175(9) Uani 1 1 d . U . . .
H7 H 0.670920 0.070228 0.496290 0.021 Uiso 1 1 calc R U . . .
C3 C 1.0864(4) 0.5278(7) 0.6779(3) 0.0190(9) Uani 1 1 d . U . . .
H3A H 1.116062 0.452243 0.732679 0.023 Uiso 1 1 calc R U . . .
H3B H 1.148102 0.556832 0.651369 0.023 Uiso 1 1 calc R U . . .
C11 C 0.6096(4) 0.4317(8) 0.3671(4) 0.0190(9) Uani 1 1 d . U . . .
H11 H 0.638217 0.548498 0.356586 0.023 Uiso 1 1 calc R U . . .
C12 C 0.2914(4) 0.2614(7) 0.2169(3) 0.0189(10) Uani 1 1 d . U . . .
H12A H 0.327210 0.291407 0.169673 0.028 Uiso 1 1 calc R U . . .
H12B H 0.279804 0.375009 0.247534 0.028 Uiso 1 1 calc R U . . .
H12C H 0.219337 0.201998 0.189931 0.028 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
I1 C1 2.092(5) . ?
O3 C4 1.338(7) . ?
O3 C3 1.450(7) . ?
O1 C9 1.378(6) . ?
O1 C12 1.423(6) . ?
O2 C4 1.202(7) . ?
N3 C5 1.422(6) . ?
N3 C2 1.420(6) . ?
N3 C4 1.397(7) . ?
N1 C5 1.272(6) . ?
N1 C6 1.425(7) . ?
N2 H2A 0.8802 . ?
N2 H2B 0.8803 . ?
N2 C5 1.368(6) . ?
C9 C10 1.386(7) . ?
C9 C8 1.395(7) . ?
C1 H1 0.9500 . ?
C1 C2 1.330(7) . ?
C2 C3 1.501(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(8) . ?
C8 H8 0.9500 . ?
C8 C7 1.389(8) . ?
C6 C7 1.391(7) . ?
C6 C11 1.394(8) . ?
C7 H7 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O3 C3 110.2(4) . . ?
C9 O1 C12 117.1(4) . . ?
C2 N3 C5 125.7(4) . . ?
C4 N3 C5 124.6(4) . . ?
C4 N3 C2 109.7(4) . . ?
C5 N1 C6 118.2(4) . . ?
H2A N2 H2B 109.4 . . ?
C5 N2 H2A 109.1 . . ?
C5 N2 H2B 109.4 . . ?
N1 C5 N3 116.9(4) . . ?
N1 C5 N2 128.4(5) . . ?
N2 C5 N3 114.6(4) . . ?
O1 C9 C10 124.0(5) . . ?
O1 C9 C8 116.3(4) . . ?
C10 C9 C8 119.7(5) . . ?
I1 C1 H1 120.2 . . ?
C2 C1 I1 119.7(4) . . ?
C2 C1 H1 120.2 . . ?
N3 C2 C3 105.2(4) . . ?
C1 C2 N3 128.2(5) . . ?
C1 C2 C3 126.6(5) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.9(5) . . ?
C11 C10 H10 120.0 . . ?
O3 C4 N3 110.2(4) . . ?
O2 C4 O3 122.5(5) . . ?
O2 C4 N3 127.3(5) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 C9 119.9(5) . . ?
C7 C8 H8 120.1 . . ?
C7 C6 N1 118.8(5) . . ?
C7 C6 C11 118.5(5) . . ?
C11 C6 N1 122.6(5) . . ?
C8 C7 C6 120.8(5) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
O3 C3 C2 104.8(4) . . ?
O3 C3 H3A 110.8 . . ?
O3 C3 H3B 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C10 C11 C6 121.1(5) . . ?
C10 C11 H11 119.4 . . ?
C6 C11 H11 119.4 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
I1 C1 C2 N3 -178.7(4) . . . . ?
I1 C1 C2 C3 1.1(7) . . . . ?
O1 C9 C10 C11 179.8(5) . . . . ?
O1 C9 C8 C7 -179.5(5) . . . . ?
N3 C2 C3 O3 1.5(5) . . . . ?
N1 C6 C7 C8 -176.9(5) . . . . ?
N1 C6 C11 C10 177.0(5) . . . . ?
C5 N3 C2 C1 2.2(8) . . . . ?
C5 N3 C2 C3 -177.7(4) . . . . ?
C5 N3 C4 O3 176.5(4) . . . . ?
C5 N3 C4 O2 -3.3(9) . . . . ?
C5 N1 C6 C7 -116.0(5) . . . . ?
C5 N1 C6 C11 67.4(7) . . . . ?
C9 C10 C11 C6 0.5(8) . . . . ?
C9 C8 C7 C6 -1.0(8) . . . . ?
C1 C2 C3 O3 -178.4(5) . . . . ?
C2 N3 C5 N1 -12.2(7) . . . . ?
C2 N3 C5 N2 163.4(4) . . . . ?
C2 N3 C4 O3 -0.8(6) . . . . ?
C2 N3 C4 O2 179.4(5) . . . . ?
C10 C9 C8 C7 1.8(8) . . . . ?
C4 O3 C3 C2 -2.1(5) . . . . ?
C4 N3 C5 N1 171.0(5) . . . . ?
C4 N3 C5 N2 -13.4(7) . . . . ?
C4 N3 C2 C1 179.4(5) . . . . ?
C4 N3 C2 C3 -0.5(5) . . . . ?
C8 C9 C10 C11 -1.6(7) . . . . ?
C6 N1 C5 N3 176.7(4) . . . . ?
C6 N1 C5 N2 1.8(8) . . . . ?
C7 C6 C11 C10 0.4(8) . . . . ?
C3 O3 C4 O2 -178.4(5) . . . . ?
C3 O3 C4 N3 1.8(6) . . . . ?
C11 C6 C7 C8 -0.1(7) . . . . ?
C12 O1 C9 C10 -7.2(7) . . . . ?
C12 O1 C9 C8 174.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_11_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2251368'
loop_
_audit_author_name
_audit_author_address
'jing zhang'
;Guangzhou University of Chinese Medicine
China
;
_audit_update_record             
;
2023-03-24 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_audit_creation_date             2022-06-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H9 Br F N3 O2'
_chemical_formula_sum            'C11 H9 Br F N3 O2'
_chemical_formula_weight         314.12
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.3126(16)
_cell_length_b                   6.7487(10)
_cell_length_c                   16.077(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.264(5)
_cell_angle_gamma                90
_cell_volume                     1158.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7737
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      60.548
_cell_measurement_theta_min      5.162
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.558
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1450 before and 0.0866 after correction.
The Ratio of minimum to maximum transmission is 0.6784.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9147
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.684
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2143
_reflns_number_total             2340
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.765
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2340
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0670P)²+0.6187P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1118
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Rotating group:
 N2(H2A,H2B)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C8(H8), C10(H10), C11(H11)
;
_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
Br1 Br 0.44906(3) 0.85334(4) 0.61399(2) 0.03173(16) Uani 1 1 d . . . . .
F1 F 0.94494(16) 0.9337(3) 0.22450(11) 0.0381(4) Uani 1 1 d . . . . .
O1 O 0.66464(19) 0.2695(3) 0.67196(14) 0.0301(4) Uani 1 1 d . . . . .
O2 O 0.8049(2) 0.1532(3) 0.61342(16) 0.0321(5) Uani 1 1 d . . . . .
N1 N 0.71038(19) 0.4624(3) 0.57361(14) 0.0211(4) Uani 1 1 d . . . . .
N2 N 0.8756(2) 0.4252(3) 0.51640(16) 0.0272(5) Uani 1 1 d . . . . .
H2A H 0.875485 0.306967 0.539447 0.033 Uiso 1 1 d R U . . .
H2B H 0.879184 0.412794 0.462796 0.033 Uiso 1 1 d R U . . .
N3 N 0.7196(2) 0.6690(3) 0.46216(16) 0.0224(5) Uani 1 1 d . . . . .
C1 C 0.5699(2) 0.7465(4) 0.56761(18) 0.0234(5) Uani 1 1 d . . . . .
H1 H 0.594703 0.817128 0.524986 0.028 Uiso 1 1 calc R U . . .
C2 C 0.6185(2) 0.5706(4) 0.59645(17) 0.0212(5) Uani 1 1 d . . . . .
C3 C 0.5864(3) 0.4434(4) 0.66346(19) 0.0269(6) Uani 1 1 d . . . . .
H3A H 0.605840 0.513455 0.720518 0.032 Uiso 1 1 calc R U . . .
H3B H 0.496597 0.407068 0.642370 0.032 Uiso 1 1 calc R U . . .
C4 C 0.7345(2) 0.2826(4) 0.61907(18) 0.0252(6) Uani 1 1 d . . . . .
C5 C 0.7686(2) 0.5236(3) 0.51201(17) 0.0201(5) Uani 1 1 d . . . . .
C6 C 0.7791(2) 0.7332(4) 0.40102(17) 0.0209(5) Uani 1 1 d . . . . .
C7 C 0.8444(2) 0.9128(4) 0.41613(18) 0.0246(5) Uani 1 1 d . . . . .
H7 H 0.850538 0.988419 0.467238 0.030 Uiso 1 1 calc R U . . .
C8 C 0.9006(3) 0.9812(4) 0.35618(19) 0.0276(6) Uani 1 1 d . . . . .
H8 H 0.945008 1.103158 0.365630 0.033 Uiso 1 1 calc R U . . .
C9 C 0.8900(3) 0.8678(4) 0.28332(19) 0.0258(6) Uani 1 1 d . . . . .
C10 C 0.8258(3) 0.6919(4) 0.26615(18) 0.0261(6) Uani 1 1 d . . . . .
H10 H 0.820150 0.617543 0.214792 0.031 Uiso 1 1 calc R U . . .
C11 C 0.7692(3) 0.6248(4) 0.3258(2) 0.0245(6) Uani 1 1 d . . . . .
H11 H 0.723533 0.503978 0.314910 0.029 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
Br1 C1 1.902(2) . ?
F1 C9 1.366(3) . ?
O1 C3 1.449(3) . ?
O1 C4 1.341(3) . ?
O2 C4 1.205(3) . ?
N1 C2 1.414(3) . ?
N1 C4 1.396(3) . ?
N1 C5 1.420(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C5 1.362(3) . ?
N3 C5 1.272(3) . ?
N3 C6 1.429(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.326(4) . ?
C2 C3 1.512(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C6 C7 1.399(4) . ?
C6 C11 1.385(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.397(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.371(4) . ?
C9 C10 1.371(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.394(4) . ?
C11 H11 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C3 110.8(2) . . ?
C2 N1 C5 125.5(2) . . ?
C4 N1 C2 110.2(2) . . ?
C4 N1 C5 124.3(2) . . ?
H2A N2 H2B 109.4 . . ?
C5 N2 H2A 109.8 . . ?
C5 N2 H2B 108.9 . . ?
C5 N3 C6 117.4(2) . . ?
Br1 C1 H1 120.9 . . ?
C2 C1 Br1 118.11(19) . . ?
C2 C1 H1 120.9 . . ?
N1 C2 C3 105.2(2) . . ?
C1 C2 N1 128.8(2) . . ?
C1 C2 C3 126.0(2) . . ?
O1 C3 C2 104.1(2) . . ?
O1 C3 H3A 110.9 . . ?
O1 C3 H3B 110.9 . . ?
C2 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
H3A C3 H3B 109.0 . . ?
O1 C4 N1 109.6(2) . . ?
O2 C4 O1 122.8(2) . . ?
O2 C4 N1 127.6(3) . . ?
N2 C5 N1 115.5(2) . . ?
N3 C5 N1 117.3(2) . . ?
N3 C5 N2 127.1(2) . . ?
C7 C6 N3 119.0(2) . . ?
C11 C6 N3 121.3(2) . . ?
C11 C6 C7 119.7(2) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.1(2) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 120.9 . . ?
C9 C8 C7 118.3(2) . . ?
C9 C8 H8 120.9 . . ?
F1 C9 C8 118.5(2) . . ?
F1 C9 C10 118.3(3) . . ?
C10 C9 C8 123.2(3) . . ?
C9 C10 H10 120.8 . . ?
C9 C10 C11 118.4(3) . . ?
C11 C10 H10 120.8 . . ?
C6 C11 C10 120.4(2) . . ?
C6 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?

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
Br1 C1 C2 N1 -178.8(2) . . . . ?
Br1 C1 C2 C3 0.4(4) . . . . ?
F1 C9 C10 C11 -179.7(2) . . . . ?
N1 C2 C3 O1 -0.5(3) . . . . ?
N3 C6 C7 C8 -178.4(2) . . . . ?
N3 C6 C11 C10 178.7(2) . . . . ?
C1 C2 C3 O1 -179.8(3) . . . . ?
C2 N1 C4 O1 -1.2(3) . . . . ?
C2 N1 C4 O2 177.9(3) . . . . ?
C2 N1 C5 N2 163.6(2) . . . . ?
C2 N1 C5 N3 -13.0(4) . . . . ?
C3 O1 C4 O2 -178.3(3) . . . . ?
C3 O1 C4 N1 0.9(3) . . . . ?
C4 O1 C3 C2 -0.3(3) . . . . ?
C4 N1 C2 C1 -179.7(3) . . . . ?
C4 N1 C2 C3 1.0(3) . . . . ?
C4 N1 C5 N2 -17.9(4) . . . . ?
C4 N1 C5 N3 165.5(2) . . . . ?
C5 N1 C2 C1 -1.0(4) . . . . ?
C5 N1 C2 C3 179.7(2) . . . . ?
C5 N1 C4 O1 -179.9(2) . . . . ?
C5 N1 C4 O2 -0.8(5) . . . . ?
C5 N3 C6 C7 -108.0(3) . . . . ?
C5 N3 C6 C11 74.4(3) . . . . ?
C6 N3 C5 N1 179.0(2) . . . . ?
C6 N3 C5 N2 2.8(4) . . . . ?
C6 C7 C8 C9 -0.2(4) . . . . ?
C7 C6 C11 C10 1.2(4) . . . . ?
C7 C8 C9 F1 -179.9(2) . . . . ?
C7 C8 C9 C10 0.7(4) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C6 -0.7(4) . . . . ?
C11 C6 C7 C8 -0.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_11_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2251367'
loop_
_audit_author_name
_audit_author_address
'jing zhang'
;Guangzhou University of Chinese Medicine
China
;
_audit_update_record             
;
2023-03-24 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_audit_creation_date             2022-06-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 Cl N3 O2'
_chemical_formula_sum            'C12 H12 Cl N3 O2'
_chemical_formula_weight         265.70
_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 0.0033 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'

_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      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   9.38970(10)
_cell_length_b                   9.38970(10)
_cell_length_c                   28.9002(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2548.03(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      60.313
_cell_measurement_theta_min      4.304
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1270 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.7843.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23658
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.437
_diffrn_reflns_theta_min         2.281
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.637
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                2558
_reflns_number_total             2838
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 913 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.95(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2838
_refine_ls_number_restraints     126
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      1.077
_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)+(0.0426P)²+1.1518P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1008
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C1 \\sim H1A \\sim H1B \\sim H1C \\sim C2 \\sim C3 \\sim H3 \\sim C4 \\sim H4
\\sim C5 \\sim C6 \\sim C7 \\sim H7: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
3. Rigid body (RIGU) restrains
 C1, H1A, H1B, H1C, C2, C3, H3, C4, H4, C5, C6, C7, H7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C7(H7)
4.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
4.e :
 C12(H12)
;
_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
Cl1 Cl 0.57806(11) 0.90598(9) 0.51259(3) 0.0641(3) Uani 1 1 d . . . . .
O1 O 0.7844(2) 0.3024(2) 0.58302(6) 0.0416(5) Uani 1 1 d . . . . .
O2 O 0.73521(19) 0.25229(19) 0.50839(6) 0.0321(4) Uani 1 1 d . . . . .
N1 N 0.4983(2) 0.6305(2) 0.55842(7) 0.0292(5) Uani 1 1 d . . . . .
H1 H 0.447697 0.613079 0.533425 0.035 Uiso 1 1 calc R U . . .
N2 N 0.6795(2) 0.5576(3) 0.60731(7) 0.0319(5) Uani 1 1 d . . . . .
H2A H 0.747746 0.497258 0.614419 0.038 Uiso 1 1 calc R U . . .
H2B H 0.663077 0.631734 0.625183 0.038 Uiso 1 1 calc R U . . .
N3 N 0.6160(2) 0.4283(2) 0.53973(7) 0.0269(4) Uani 1 1 d . . . . .
C1 C 0.2902(4) 0.8503(6) 0.69859(13) 0.0762(13) Uani 1 1 d . U . . .
H1A H 0.330130 0.919741 0.720335 0.114 Uiso 1 1 calc R U . . .
H1B H 0.304952 0.753856 0.710607 0.114 Uiso 1 1 calc R U . . .
H1C H 0.187934 0.867913 0.694871 0.114 Uiso 1 1 calc R U . . .
C2 C 0.3636(3) 0.8650(4) 0.65216(11) 0.0510(7) Uani 1 1 d . U . . .
C3 C 0.3954(4) 0.9980(4) 0.63372(15) 0.0634(8) Uani 1 1 d . U . . .
H3 H 0.372559 1.081349 0.650815 0.076 Uiso 1 1 calc R U . . .
C4 C 0.4590(4) 1.0108(4) 0.59148(15) 0.0619(9) Uani 1 1 d . U . . .
H4 H 0.478653 1.102767 0.579354 0.074 Uiso 1 1 calc R U . . .
C5 C 0.4955(3) 0.8901(3) 0.56590(12) 0.0450(7) Uani 1 1 d . U . . .
C6 C 0.4652(3) 0.7549(3) 0.58380(9) 0.0324(5) Uani 1 1 d . U . . .
C7 C 0.3991(3) 0.7447(3) 0.62661(10) 0.0386(6) Uani 1 1 d . U . . .
H7 H 0.377557 0.653253 0.638771 0.046 Uiso 1 1 calc R U . . .
C8 C 0.6010(3) 0.5369(2) 0.56950(8) 0.0255(5) Uani 1 1 d . . . . .
C9 C 0.7162(3) 0.3289(3) 0.54770(9) 0.0291(5) Uani 1 1 d . . . . .
C10 C 0.8492(3) 0.1501(3) 0.50982(11) 0.0431(7) Uani 1 1 d . . . . .
H10A H 0.831478 0.078941 0.534446 0.052 Uiso 1 1 calc R U . . .
H10B H 0.940729 0.198335 0.516347 0.052 Uiso 1 1 calc R U . . .
C11 C 0.8544(3) 0.0809(4) 0.46498(11) 0.0448(7) Uani 1 1 d . . . . .
C12 C 0.8569(5) 0.0229(5) 0.42921(13) 0.0739(14) Uani 1 1 d . . . . .
H12 H 0.858998 -0.024267 0.400135 0.089 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C5 1.731(4) . ?
O1 C9 1.231(3) . ?
O2 C9 1.357(3) . ?
O2 C10 1.438(3) . ?
N1 H1 0.8800 . ?
N1 C6 1.413(3) . ?
N1 C8 1.344(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C8 1.332(3) . ?
N3 C8 1.341(3) . ?
N3 C9 1.345(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.515(5) . ?
C2 C3 1.391(6) . ?
C2 C7 1.390(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.364(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.396(5) . ?
C5 C6 1.401(4) . ?
C6 C7 1.388(4) . ?
C7 H7 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.450(4) . ?
C11 C12 1.169(5) . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O2 C10 115.3(2) . . ?
C6 N1 H1 117.5 . . ?
C8 N1 H1 117.5 . . ?
C8 N1 C6 125.1(2) . . ?
H2A N2 H2B 120.0 . . ?
C8 N2 H2A 120.0 . . ?
C8 N2 H2B 120.0 . . ?
C8 N3 C9 119.4(2) . . ?
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 . . ?
C3 C2 C1 121.3(3) . . ?
C7 C2 C1 120.4(4) . . ?
C7 C2 C3 118.3(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(4) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 Cl1 120.8(3) . . ?
C4 C5 C6 119.4(3) . . ?
C6 C5 Cl1 119.8(2) . . ?
C5 C6 N1 120.9(3) . . ?
C7 C6 N1 120.3(2) . . ?
C7 C6 C5 118.8(3) . . ?
C2 C7 H7 119.1 . . ?
C6 C7 C2 121.7(3) . . ?
C6 C7 H7 119.1 . . ?
N2 C8 N1 119.8(2) . . ?
N2 C8 N3 125.4(2) . . ?
N3 C8 N1 114.8(2) . . ?
O1 C9 O2 121.2(2) . . ?
O1 C9 N3 130.3(3) . . ?
N3 C9 O2 108.5(2) . . ?
O2 C10 H10A 110.2 . . ?
O2 C10 H10B 110.2 . . ?
O2 C10 C11 107.3(2) . . ?
H10A C10 H10B 108.5 . . ?
C11 C10 H10A 110.2 . . ?
C11 C10 H10B 110.2 . . ?
C12 C11 C10 178.6(4) . . ?
C11 C12 H12 180.0 . . ?

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 C5 C6 N1 -1.4(4) . . . . ?
Cl1 C5 C6 C7 180.0(2) . . . . ?
N1 C6 C7 C2 -179.2(2) . . . . ?
C1 C2 C3 C4 -178.7(3) . . . . ?
C1 C2 C7 C6 179.4(3) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C3 C2 C7 C6 0.3(4) . . . . ?
C3 C4 C5 Cl1 -179.3(3) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C4 C5 C6 N1 178.8(3) . . . . ?
C4 C5 C6 C7 0.2(4) . . . . ?
C5 C6 C7 C2 -0.6(4) . . . . ?
C6 N1 C8 N2 0.8(4) . . . . ?
C6 N1 C8 N3 -178.3(2) . . . . ?
C7 C2 C3 C4 0.5(5) . . . . ?
C8 N1 C6 C5 110.0(3) . . . . ?
C8 N1 C6 C7 -71.3(3) . . . . ?
C8 N3 C9 O1 15.2(4) . . . . ?
C8 N3 C9 O2 -165.1(2) . . . . ?
C9 O2 C10 C11 -179.2(2) . . . . ?
C9 N3 C8 N1 179.9(2) . . . . ?
C9 N3 C8 N2 0.8(4) . . . . ?
C10 O2 C9 O1 -6.1(4) . . . . ?
C10 O2 C9 N3 174.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
