# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 2233686'
loop_
_audit_author_name
_audit_author_address
'Sheng Zhang'
;Anhui University
China
;
_audit_update_record             
;
2022-12-31 deposited with the CCDC.	2023-05-24 downloaded from the CCDC.
;
_audit_creation_date             2022-10-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C19 H20 Cl N2)'
_chemical_formula_sum            'C18 H18 Cl N3'
_chemical_formula_weight         311.80
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.192(16)
_cell_length_b                   10.25(2)
_cell_length_c                   11.264(11)
_cell_angle_alpha                108.81(15)
_cell_angle_beta                 108.25(12)
_cell_angle_gamma                99.05(16)
_cell_volume                     815(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5357
_cell_measurement_temperature    295
_cell_measurement_theta_max      69.73
_cell_measurement_theta_min      4.50
_shelx_estimated_absorpt_T_max   0.805
_shelx_estimated_absorpt_T_min   0.776
_exptl_absorpt_coefficient_mu    2.059
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6152
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        66.597
_diffrn_reflns_theta_max         66.597
_diffrn_reflns_theta_min         4.502
_diffrn_ambient_temperature      295
_diffrn_detector                 Pilatus300K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS 300K'
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      '1298 frames, detector distance = 40 mm'
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 mm, 0.6 diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'GeniX 3D HF Cu'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2055
_reflns_number_total             2772
_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       
;
X-Area Recipe 1.37.0.0 (STOE, 2021)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.175.0 (STOE, 2021)
;
_computing_data_reduction        
;
X-Area Integrate 2.5.1.0 (STOE, 2021)
X-Area LANA 2.6.2.0 (STOE, 2021)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 2.0, Darmstadt 2021
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.166
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2772
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0736
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1781P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1903
_refine_ls_wR_factor_ref         0.2431
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C13(H13), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C12(H12A,H12B,H12C)
;
_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 0.75775(14) 0.33579(11) -0.02457(10) 0.0600(4) Uani 1 1 d . . . . .
N1 N 0.6801(3) 0.5051(3) 0.2231(3) 0.0309(6) Uani 1 1 d . . . . .
N2 N 0.4534(3) 0.4729(3) 0.2951(3) 0.0302(6) Uani 1 1 d . . . . .
N3 N 0.2424(4) 0.4059(3) 0.3687(3) 0.0438(8) Uani 1 1 d . . . . .
C1 C 0.1654(5) 0.1417(4) 0.2325(4) 0.0517(10) Uani 1 1 d . . . . .
H1 H 0.077586 0.115511 0.263208 0.062 Uiso 1 1 calc R U . . .
C2 C 0.2039(5) 0.0399(4) 0.1410(4) 0.0528(10) Uani 1 1 d . . . . .
H2 H 0.141403 -0.056454 0.109590 0.063 Uiso 1 1 calc R U . . .
C3 C 0.3334(6) 0.0769(4) 0.0944(4) 0.0513(10) Uani 1 1 d . . . . .
H3 H 0.355527 0.004799 0.031628 0.062 Uiso 1 1 calc R U . . .
C4 C 0.4322(5) 0.2193(4) 0.1385(4) 0.0377(8) Uani 1 1 d . . . . .
H4 H 0.520375 0.244357 0.107719 0.045 Uiso 1 1 calc R U . . .
C5 C 0.3909(4) 0.3216(3) 0.2314(3) 0.0318(7) Uani 1 1 d . . . . .
C6 C 0.2592(4) 0.2837(4) 0.2783(3) 0.0377(8) Uani 1 1 d . . . . .
C7 C 0.3538(4) 0.5105(4) 0.3742(4) 0.0392(8) Uani 1 1 d . . . . .
H7 H 0.368089 0.605582 0.427188 0.047 Uiso 1 1 calc R U . . .
C8 C 0.5934(4) 0.5654(3) 0.2877(3) 0.0281(7) Uani 1 1 d . . . . .
C9 C 0.6145(5) 0.7223(4) 0.3593(4) 0.0429(9) Uani 1 1 d . . . . .
H9A H 0.506798 0.744201 0.317402 0.064 Uiso 1 1 calc R U . . .
H9B H 0.713875 0.778986 0.352869 0.064 Uiso 1 1 calc R U . . .
H9C H 0.636237 0.743815 0.453358 0.064 Uiso 1 1 calc R U . . .
C10 C 0.8277(4) 0.5841(3) 0.2024(3) 0.0310(7) Uani 1 1 d . . . . .
C11 C 0.9108(5) 0.4705(4) 0.1399(3) 0.0383(8) Uani 1 1 d . . . . .
H11A H 0.950583 0.423536 0.201367 0.046 Uiso 1 1 calc R U . . .
H11B H 1.015509 0.517752 0.130478 0.046 Uiso 1 1 calc R U . . .
C12 C 0.7547(5) 0.6549(4) 0.1040(4) 0.0453(9) Uani 1 1 d . . . . .
H12A H 0.653018 0.586167 0.025871 0.068 Uiso 1 1 calc R U . . .
H12B H 0.846518 0.687549 0.075505 0.068 Uiso 1 1 calc R U . . .
H12C H 0.719054 0.735270 0.149075 0.068 Uiso 1 1 calc R U . . .
C13 C 1.1027(5) 0.8029(4) 0.3376(4) 0.0423(9) Uani 1 1 d . . . . .
H13 H 1.082962 0.819822 0.258686 0.051 Uiso 1 1 calc R U . . .
C14 C 0.9845(4) 0.6889(3) 0.3358(3) 0.0307(7) Uani 1 1 d . . . . .
C15 C 1.0190(4) 0.6657(4) 0.4554(3) 0.0387(8) Uani 1 1 d . . . . .
H15 H 0.941456 0.589886 0.456591 0.046 Uiso 1 1 calc R U . . .
C16 C 1.1669(5) 0.7540(5) 0.5723(4) 0.0507(10) Uani 1 1 d . . . . .
H16 H 1.189644 0.736723 0.651235 0.061 Uiso 1 1 calc R U . . .
C17 C 1.2799(5) 0.8670(5) 0.5716(4) 0.0561(11) Uani 1 1 d . . . . .
H17 H 1.378064 0.927642 0.650752 0.067 Uiso 1 1 calc R U . . .
C18 C 1.2493(5) 0.8915(4) 0.4550(5) 0.0551(11) Uani 1 1 d . . . . .
H18 H 1.327370 0.967885 0.454967 0.066 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 C11 1.806(6) . ?
N1 C8 1.260(4) . ?
N1 C10 1.470(5) . ?
N2 C5 1.409(6) . ?
N2 C7 1.394(5) . ?
N2 C8 1.411(5) . ?
N3 C6 1.395(6) . ?
N3 C7 1.265(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.365(7) . ?
C1 C6 1.375(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.391(5) . ?
C5 C6 1.397(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.502(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.529(6) . ?
C10 C12 1.534(5) . ?
C10 C14 1.542(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C14 1.385(5) . ?
C13 C18 1.380(7) . ?
C14 C15 1.393(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.369(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.370(7) . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C10 123.6(3) . . ?
C5 N2 C8 127.9(3) . . ?
C7 N2 C5 104.6(3) . . ?
C7 N2 C8 127.4(3) . . ?
C7 N3 C6 105.1(3) . . ?
C2 C1 H1 120.7 . . ?
C2 C1 C6 118.7(4) . . ?
C6 C1 H1 120.7 . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.3(4) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 121.9(4) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 122.0 . . ?
C5 C4 C3 116.0(3) . . ?
C5 C4 H4 122.0 . . ?
C4 C5 N2 133.4(3) . . ?
C4 C5 C6 121.9(3) . . ?
C6 C5 N2 104.7(3) . . ?
N3 C6 C5 110.5(3) . . ?
C1 C6 N3 129.3(3) . . ?
C1 C6 C5 120.1(4) . . ?
N2 C7 H7 122.5 . . ?
N3 C7 N2 115.1(4) . . ?
N3 C7 H7 122.5 . . ?
N1 C8 N2 116.0(3) . . ?
N1 C8 C9 130.3(3) . . ?
N2 C8 C9 113.7(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C11 105.3(3) . . ?
N1 C10 C12 110.3(3) . . ?
N1 C10 C14 113.9(3) . . ?
C11 C10 C12 110.1(3) . . ?
C11 C10 C14 103.4(3) . . ?
C12 C10 C14 113.4(3) . . ?
Cl1 C11 H11A 108.9 . . ?
Cl1 C11 H11B 108.9 . . ?
C10 C11 Cl1 113.2(3) . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.8 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 H13 119.6 . . ?
C18 C13 H13 119.6 . . ?
C18 C13 C14 120.8(4) . . ?
C13 C14 C10 120.8(3) . . ?
C13 C14 C15 118.1(3) . . ?
C15 C14 C10 121.0(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.8(3) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.8(4) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.5(4) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 H18 120.0 . . ?
C17 C18 C13 120.0(4) . . ?
C17 C18 H18 120.0 . . ?

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 C10 C11 Cl1 63.1(3) . . . . ?
N1 C10 C14 C13 -158.6(3) . . . . ?
N1 C10 C14 C15 26.2(4) . . . . ?
N2 C5 C6 N3 -0.8(3) . . . . ?
N2 C5 C6 C1 178.2(3) . . . . ?
C1 C2 C3 C4 0.4(7) . . . . ?
C2 C1 C6 N3 178.8(4) . . . . ?
C2 C1 C6 C5 0.0(6) . . . . ?
C2 C3 C4 C5 -0.6(6) . . . . ?
C3 C4 C5 N2 -177.3(3) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C4 C5 C6 N3 -179.2(3) . . . . ?
C4 C5 C6 C1 -0.2(5) . . . . ?
C5 N2 C7 N3 0.4(4) . . . . ?
C5 N2 C8 N1 -4.7(4) . . . . ?
C5 N2 C8 C9 175.2(3) . . . . ?
C6 N3 C7 N2 -0.9(4) . . . . ?
C6 C1 C2 C3 -0.1(7) . . . . ?
C7 N2 C5 C4 178.3(4) . . . . ?
C7 N2 C5 C6 0.3(3) . . . . ?
C7 N2 C8 N1 170.8(3) . . . . ?
C7 N2 C8 C9 -9.3(4) . . . . ?
C7 N3 C6 C1 -177.8(4) . . . . ?
C7 N3 C6 C5 1.1(4) . . . . ?
C8 N1 C10 C11 171.3(3) . . . . ?
C8 N1 C10 C12 -69.9(4) . . . . ?
C8 N1 C10 C14 58.8(4) . . . . ?
C8 N2 C5 C4 -5.3(5) . . . . ?
C8 N2 C5 C6 176.6(3) . . . . ?
C8 N2 C7 N3 -175.9(3) . . . . ?
C10 N1 C8 N2 178.7(3) . . . . ?
C10 N1 C8 C9 -1.3(5) . . . . ?
C10 C14 C15 C16 175.4(3) . . . . ?
C11 C10 C14 C13 87.8(4) . . . . ?
C11 C10 C14 C15 -87.5(4) . . . . ?
C12 C10 C11 Cl1 -55.8(3) . . . . ?
C12 C10 C14 C13 -31.4(4) . . . . ?
C12 C10 C14 C15 153.3(3) . . . . ?
C13 C14 C15 C16 0.0(5) . . . . ?
C14 C10 C11 Cl1 -177.2(2) . . . . ?
C14 C13 C18 C17 0.3(6) . . . . ?
C14 C15 C16 C17 1.0(6) . . . . ?
C15 C16 C17 C18 -1.3(6) . . . . ?
C16 C17 C18 C13 0.7(7) . . . . ?
C18 C13 C14 C10 -176.0(3) . . . . ?
C18 C13 C14 C15 -0.6(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_STOE_detector_distance          '40.0 mm'
_STOE_detector_pixelsize_x       '0.172 mm'
_STOE_detector_pixelsize_y       '0.172 mm'
_STOE_detector_size_x            '8.4 cm'
_STOE_detector_size_y            '10.6 cm'
_STOE_evaluation_integration_A   6.5
_STOE_evaluation_integration_B   0.8
_STOE_evaluation_integration_EMS 0.020
_STOE_evaluation_LANA_BIS_l_even_max -
_STOE_evaluation_LANA_BIS_l_odd_max -
_STOE_evaluation_LANA_BOS_l_even_max 4
_STOE_evaluation_LANA_BOS_l_odd_max 1
_STOE_evaluation_LANA_completeness 93.9
_STOE_evaluation_LANA_DXS_max_order 3
_STOE_evaluation_LANA_DYS_max_order 3
_STOE_evaluation_LANA_FS_max_order 3
_STOE_evaluation_LANA_max_2theta_available 139.1
_STOE_evaluation_LANA_max_2theta_desired 139.1
_STOE_evaluation_LANA_mean_redundancy 2.2
_STOE_evaluation_LANA_number_refls_after_OR 6292
_STOE_evaluation_LANA_number_refls_outliers 1025
_STOE_evaluation_LANA_number_refls_total 7317
_STOE_evaluation_LANA_number_refls_unique 2880
_STOE_evaluation_LANA_number_refls_written 6292
_STOE_evaluation_LANA_OR_c1      0.035
_STOE_evaluation_LANA_OR_c2      0
_STOE_evaluation_LANA_OR_c3      0
_STOE_evaluation_LANA_OR_c4      0.7
_STOE_evaluation_LANA_point_group -1
_STOE_evaluation_LANA_table      
;
#----------------------------------------------------------------------------
2Theta          15.6   30.2   44.8   59.4   74.0   88.6  103.2  117.8  132.4
#----------------------------------------------------------------------------
<Resolution>    5.39   2.88   1.96   1.54   1.28   1.10   0.99   0.90   0.85
N(total)          47    134    315   1185   1513   1352   1227   1045    499
<Redundancy>     1.5    1.3    1.5    3.0    2.9    2.4    2.1    1.9    1.5
Complet. [%%]   100.0   98.0   94.1   99.7   99.8   99.8   98.5   94.3   71.6
<I/sigma>      181.0   85.6   37.7   20.1   12.6    9.1    6.2    4.2    3.6
R(int)         0.027  0.083  0.071  0.035  0.047  0.051  0.069  0.089  0.104
#----------------------------------------------------------------------------
;
_STOE_measurement_identifier     2
_STOE_measurement_max_exposure_per_frame '0.5 s'
_STOE_measurement_mean_exposure_per_frame '0.5 s'
_STOE_measurement_min_exposure_per_frame '0.3 s'
_STOE_measurement_total_exposure_time '10 min'
_STOE_measurement_total_frame_number 1298
_STOE_measurement_total_run_number 27
_STOE_measurement_tube_power     '30.0 W'
####################################################################### 
# 
# 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 2233688'
loop_
_audit_author_name
_audit_author_address
'Sheng Zhang'
;Anhui University
China
;
_audit_update_record             
;
2022-12-31 deposited with the CCDC.	2023-05-24 downloaded from the CCDC.
;
_audit_creation_date             2022-10-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 Cl3 N3'
_chemical_formula_sum            'C17 H14 Cl3 N3'
_chemical_formula_weight         366.66
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   11.0153(11)
_cell_length_b                   11.3962(12)
_cell_length_c                   13.8948(14)
_cell_angle_alpha                90
_cell_angle_beta                 112.288(8)
_cell_angle_gamma                90
_cell_volume                     1613.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6658
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.39
_cell_measurement_theta_min      3.12
_shelx_estimated_absorpt_T_max   0.627
_shelx_estimated_absorpt_T_min   0.577
_exptl_absorpt_coefficient_mu    5.149
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13138
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         69.446
_diffrn_reflns_theta_min         4.396
_diffrn_ambient_temperature      150
_diffrn_detector                 Pilatus300K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS 300K'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      '1538 frames, detector distance = 40 mm'
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 mm, 0.6 diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'GeniX 3D HF Cu'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2492
_reflns_number_total             2922
_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       'X-Area Recipe 1.37.0.0 (STOE, 2021)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.175.0 (STOE, 2021)'
_computing_data_reduction        
;
X-Area Integrate 2.5.1.0 (STOE, 2021)
X-Area LANA 2.6.2.0 (STOE, 2021)
;
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.810
_refine_diff_density_min         -0.785
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2922
_refine_ls_number_restraints     150
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0687P)²+1.2259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1245
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
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.a Ternary CH refined with riding coordinates:
 C00A(H00A)
3.b Secondary CH2 refined with riding coordinates:
 C00H(H00C,H00D)
3.c Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C00L(H00L), C00M(H00M), C00G(H00G), C00B(H00B), C00J(H00J),
 C00K(H00K), C00E(H00E)
3.d Fitted hexagon refined as free rotating group:
 C007(C00F,C00I,C00L,C00M,C00G), C00D(C009,C00C,C00J,C00K,C00E)
3.e Idealised Me refined as rotating group:
 C00N(H00F,H00H,H00N)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl01 Cl 0.60569(6) 0.41799(6) 0.60852(5) 0.0300(2) Uani 1 1 d . U . . .
Cl02 Cl 0.70348(6) 0.04172(6) 0.40281(5) 0.0292(2) Uani 1 1 d . U . . .
Cl03 Cl 0.84595(7) 0.08205(6) 0.68683(5) 0.0368(2) Uani 1 1 d . U . . .
N004 N 0.83773(19) 0.55426(19) 0.45490(16) 0.0208(4) Uani 1 1 d . U . . .
N005 N 0.82881(19) 0.38424(19) 0.53734(16) 0.0203(4) Uani 1 1 d . U . . .
N006 N 0.8641(2) 0.7345(2) 0.39844(19) 0.0304(5) Uani 1 1 d . U . . .
C007 C 0.89193(16) 0.62457(12) 0.54257(11) 0.0217(5) Uani 1 1 d G U . . .
C00F C 0.90790(16) 0.73465(14) 0.50593(9) 0.0246(5) Uani 1 1 d G U . . .
C00I C 0.95941(17) 0.82644(11) 0.57537(13) 0.0288(6) Uani 1 1 d G U . . .
H00I H 0.970322 0.901683 0.550325 0.035 Uiso 1 1 calc R U . . .
C00L C 0.99495(17) 0.80815(12) 0.68147(12) 0.0322(6) Uani 1 1 d G U . . .
H00L H 1.030156 0.870891 0.728929 0.039 Uiso 1 1 calc R U . . .
C00M C 0.97898(19) 0.69807(15) 0.71811(9) 0.0335(6) Uani 1 1 d G U . . .
H00M H 1.003275 0.685568 0.790625 0.040 Uiso 1 1 calc R U . . .
C00G C 0.92747(18) 0.60627(11) 0.64867(12) 0.0275(6) Uani 1 1 d G U . . .
H00G H 0.916559 0.531036 0.673717 0.033 Uiso 1 1 calc R U . . .
C008 C 0.8015(2) 0.4335(2) 0.45019(19) 0.0188(5) Uani 1 1 d . U . . .
C00A C 0.7965(2) 0.2605(2) 0.54437(18) 0.0196(5) Uani 1 1 d . U . . .
H00A H 0.839724 0.212160 0.506346 0.024 Uiso 1 1 calc R U . . .
C00B C 0.8252(3) 0.6281(3) 0.3726(2) 0.0279(6) Uani 1 1 d . U . . .
H00B H 0.790551 0.602341 0.302320 0.034 Uiso 1 1 calc R U . . .
C00D C 0.60156(13) 0.13177(13) 0.43819(12) 0.0211(5) Uani 1 1 d G U . . .
C009 C 0.64638(11) 0.23010(14) 0.50088(12) 0.0195(5) Uani 1 1 d G U . . .
C00C C 0.55892(14) 0.29896(12) 0.52656(12) 0.0231(5) Uani 1 1 d G U . . .
C00J C 0.42664(13) 0.26950(14) 0.48955(14) 0.0297(6) Uani 1 1 d G U . . .
H00J H 0.366864 0.316560 0.507099 0.036 Uiso 1 1 calc R U . . .
C00K C 0.38182(11) 0.17117(16) 0.42685(14) 0.0301(6) Uani 1 1 d G U . . .
H00K H 0.291408 0.151026 0.401558 0.036 Uiso 1 1 calc R U . . .
C00E C 0.46928(14) 0.10230(13) 0.40117(12) 0.0261(6) Uani 1 1 d G U . . .
H00E H 0.438643 0.035099 0.358325 0.031 Uiso 1 1 calc R U . . .
C00H C 0.8623(3) 0.2336(2) 0.66079(19) 0.0243(5) Uani 1 1 d . U . . .
H00C H 0.821763 0.282355 0.699536 0.029 Uiso 1 1 calc R U . . .
H00D H 0.956516 0.254160 0.685423 0.029 Uiso 1 1 calc R U . . .
C00N C 0.7345(3) 0.3841(3) 0.3430(2) 0.0285(6) Uani 1 1 d . U . . .
H00F H 0.645833 0.416747 0.311437 0.043 Uiso 1 1 calc R U . . .
H00H H 0.729331 0.298522 0.347102 0.043 Uiso 1 1 calc R U . . .
H00N H 0.784687 0.404771 0.300323 0.043 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl01 C00C 1.7197(13) . ?
Cl02 C00D 1.7244(13) . ?
Cl03 C00H 1.787(3) . ?
N004 C007 1.390(2) . ?
N004 C008 1.428(3) . ?
N004 C00B 1.384(3) . ?
N005 C008 1.263(3) . ?
N005 C00A 1.467(3) . ?
N006 C00F 1.385(3) . ?
N006 C00B 1.291(4) . ?
C007 C00F 1.3900 . ?
C007 C00G 1.3900 . ?
C00F C00I 1.3900 . ?
C00I H00I 0.9500 . ?
C00I C00L 1.3900 . ?
C00L H00L 0.9500 . ?
C00L C00M 1.3900 . ?
C00M H00M 0.9500 . ?
C00M C00G 1.3900 . ?
C00G H00G 0.9500 . ?
C008 C00N 1.499(4) . ?
C00A H00A 1.0000 . ?
C00A C009 1.569(2) . ?
C00A C00H 1.532(3) . ?
C00B H00B 0.9500 . ?
C00D C009 1.3900 . ?
C00D C00E 1.3900 . ?
C009 C00C 1.3900 . ?
C00C C00J 1.3900 . ?
C00J H00J 0.9500 . ?
C00J C00K 1.3900 . ?
C00K H00K 0.9500 . ?
C00K C00E 1.3900 . ?
C00E H00E 0.9500 . ?
C00H H00C 0.9900 . ?
C00H H00D 0.9900 . ?
C00N H00F 0.9800 . ?
C00N H00H 0.9800 . ?
C00N H00N 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
C007 N004 C008 128.01(19) . . ?
C00B N004 C007 104.4(2) . . ?
C00B N004 C008 127.6(2) . . ?
C008 N005 C00A 121.0(2) . . ?
C00B N006 C00F 104.1(2) . . ?
N004 C007 C00F 105.74(13) . . ?
N004 C007 C00G 134.26(13) . . ?
C00F C007 C00G 120.0 . . ?
N006 C00F C007 110.70(14) . . ?
N006 C00F C00I 129.29(14) . . ?
C007 C00F C00I 120.0 . . ?
C00F C00I H00I 120.0 . . ?
C00F C00I C00L 120.0 . . ?
C00L C00I H00I 120.0 . . ?
C00I C00L H00L 120.0 . . ?
C00M C00L C00I 120.0 . . ?
C00M C00L H00L 120.0 . . ?
C00L C00M H00M 120.0 . . ?
C00L C00M C00G 120.0 . . ?
C00G C00M H00M 120.0 . . ?
C007 C00G H00G 120.0 . . ?
C00M C00G C007 120.0 . . ?
C00M C00G H00G 120.0 . . ?
N004 C008 C00N 115.5(2) . . ?
N005 C008 N004 115.1(2) . . ?
N005 C008 C00N 129.4(2) . . ?
N005 C00A H00A 108.6 . . ?
N005 C00A C009 115.69(18) . . ?
N005 C00A C00H 103.49(19) . . ?
C009 C00A H00A 108.6 . . ?
C00H C00A H00A 108.6 . . ?
C00H C00A C009 111.70(18) . . ?
N004 C00B H00B 122.5 . . ?
N006 C00B N004 115.0(2) . . ?
N006 C00B H00B 122.5 . . ?
C009 C00D Cl02 122.92(9) . . ?
C009 C00D C00E 120.0 . . ?
C00E C00D Cl02 117.08(9) . . ?
C00D C009 C00A 119.43(12) . . ?
C00D C009 C00C 120.0 . . ?
C00C C009 C00A 120.56(12) . . ?
C009 C00C Cl01 123.55(9) . . ?
C00J C00C Cl01 116.38(9) . . ?
C00J C00C C009 120.0 . . ?
C00C C00J H00J 120.0 . . ?
C00C C00J C00K 120.0 . . ?
C00K C00J H00J 120.0 . . ?
C00J C00K H00K 120.0 . . ?
C00E C00K C00J 120.0 . . ?
C00E C00K H00K 120.0 . . ?
C00D C00E H00E 120.0 . . ?
C00K C00E C00D 120.0 . . ?
C00K C00E H00E 120.0 . . ?
Cl03 C00H H00C 109.4 . . ?
Cl03 C00H H00D 109.4 . . ?
C00A C00H Cl03 111.32(17) . . ?
C00A C00H H00C 109.4 . . ?
C00A C00H H00D 109.4 . . ?
H00C C00H H00D 108.0 . . ?
C008 C00N H00F 109.5 . . ?
C008 C00N H00H 109.5 . . ?
C008 C00N H00N 109.5 . . ?
H00F C00N H00H 109.5 . . ?
H00F C00N H00N 109.5 . . ?
H00H C00N H00N 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
Cl01 C00C C00J C00K -176.97(13) . . . . ?
Cl02 C00D C009 C00A -1.46(17) . . . . ?
Cl02 C00D C009 C00C -179.94(14) . . . . ?
Cl02 C00D C00E C00K 179.95(13) . . . . ?
N004 C007 C00F N006 0.53(17) . . . . ?
N004 C007 C00F C00I 179.28(15) . . . . ?
N004 C007 C00G C00M -179.0(2) . . . . ?
N005 C00A C009 C00D 135.30(16) . . . . ?
N005 C00A C009 C00C -46.2(2) . . . . ?
N005 C00A C00H Cl03 -175.59(16) . . . . ?
N006 C00F C00I C00L 178.5(2) . . . . ?
C007 N004 C008 N005 -3.9(3) . . . . ?
C007 N004 C008 C00N 175.0(2) . . . . ?
C007 N004 C00B N006 -0.3(3) . . . . ?
C007 C00F C00I C00L 0.0 . . . . ?
C00F N006 C00B N004 0.6(3) . . . . ?
C00F C007 C00G C00M 0.0 . . . . ?
C00F C00I C00L C00M 0.0 . . . . ?
C00I C00L C00M C00G 0.0 . . . . ?
C00L C00M C00G C007 0.0 . . . . ?
C00G C007 C00F N006 -178.75(17) . . . . ?
C00G C007 C00F C00I 0.0 . . . . ?
C008 N004 C007 C00F -179.49(19) . . . . ?
C008 N004 C007 C00G -0.4(3) . . . . ?
C008 N004 C00B N006 179.0(2) . . . . ?
C008 N005 C00A C009 -64.9(3) . . . . ?
C008 N005 C00A C00H 172.6(2) . . . . ?
C00A N005 C008 N004 179.63(19) . . . . ?
C00A N005 C008 C00N 0.9(4) . . . . ?
C00A C009 C00C Cl01 -1.72(17) . . . . ?
C00A C009 C00C C00J -178.46(17) . . . . ?
C00B N004 C007 C00F -0.16(19) . . . . ?
C00B N004 C007 C00G 178.97(16) . . . . ?
C00B N004 C008 N005 176.9(2) . . . . ?
C00B N004 C008 C00N -4.2(3) . . . . ?
C00B N006 C00F C007 -0.7(2) . . . . ?
C00B N006 C00F C00I -179.29(16) . . . . ?
C00D C009 C00C Cl01 176.74(14) . . . . ?
C00D C009 C00C C00J 0.0 . . . . ?
C009 C00A C00H Cl03 59.3(2) . . . . ?
C009 C00D C00E C00K 0.0 . . . . ?
C009 C00C C00J C00K 0.0 . . . . ?
C00C C00J C00K C00E 0.0 . . . . ?
C00J C00K C00E C00D 0.0 . . . . ?
C00E C00D C009 C00A 178.48(17) . . . . ?
C00E C00D C009 C00C 0.0 . . . . ?
C00H C00A C009 C00D -106.66(19) . . . . ?
C00H C00A C009 C00C 71.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_STOE_detector_distance          '40.0 mm'
_STOE_detector_pixelsize_x       '0.172 mm'
_STOE_detector_pixelsize_y       '0.172 mm'
_STOE_detector_size_x            '8.4 cm'
_STOE_detector_size_y            '10.6 cm'
_STOE_evaluation_integration_A   6.0
_STOE_evaluation_integration_B   0.5
_STOE_evaluation_integration_EMS 0.020
_STOE_evaluation_LANA_BIS_l_even_max -
_STOE_evaluation_LANA_BIS_l_odd_max -
_STOE_evaluation_LANA_BOS_l_even_max 4
_STOE_evaluation_LANA_BOS_l_odd_max 1
_STOE_evaluation_LANA_completeness 92.9
_STOE_evaluation_LANA_DXS_max_order -
_STOE_evaluation_LANA_DYS_max_order 3
_STOE_evaluation_LANA_FS_max_order 3
_STOE_evaluation_LANA_max_2theta_available 138.9
_STOE_evaluation_LANA_max_2theta_desired 138.9
_STOE_evaluation_LANA_mean_redundancy 2.4
_STOE_evaluation_LANA_number_refls_after_OR 13541
_STOE_evaluation_LANA_number_refls_outliers 1970
_STOE_evaluation_LANA_number_refls_total 15511
_STOE_evaluation_LANA_number_refls_unique 5633
_STOE_evaluation_LANA_number_refls_written 13541
_STOE_evaluation_LANA_OR_c1      0.035
_STOE_evaluation_LANA_OR_c2      0
_STOE_evaluation_LANA_OR_c3      0
_STOE_evaluation_LANA_OR_c4      0.7
_STOE_evaluation_LANA_point_group 2
_STOE_evaluation_LANA_table      
;
#----------------------------------------------------------------------------
2Theta          13.6   28.4   43.2   58.0   72.8   87.6  102.4  117.2  132.0
#----------------------------------------------------------------------------
<Resolution>    5.61   2.98   2.00   1.57   1.30   1.11   0.99   0.90   0.85
N(total)          61    139    360   2301   3046   3107   2892   2399   1206
<Redundancy>     1.5    1.1    1.3    3.1    3.1    2.7    2.4    2.1    1.7
Complet. [%%]    74.0   72.0   73.9   99.3  100.0   99.7   99.0   97.0   75.6
<I/sigma>       92.9  104.1   39.7   23.3   15.3   12.1    8.9    8.5    8.4
R(int)         0.034  0.019  0.028  0.024  0.026  0.026  0.036  0.039  0.041
#----------------------------------------------------------------------------
;
_STOE_measurement_identifier     1
_STOE_measurement_max_exposure_per_frame '0.6 s'
_STOE_measurement_mean_exposure_per_frame '0.5 s'
_STOE_measurement_min_exposure_per_frame '0.2 s'
_STOE_measurement_total_exposure_time '13 min'
_STOE_measurement_total_frame_number 1538
_STOE_measurement_total_run_number 30
_STOE_measurement_tube_power     '30.0 W'
####################################################################### 
# 
# 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 2233687'
loop_
_audit_author_name
_audit_author_address
'Sheng Zhang'
;Anhui University
China
;
_audit_update_record             
;
2022-12-31 deposited with the CCDC.	2023-05-24 downloaded from the CCDC.
;
_audit_creation_date             2022-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 Br Cl3 N3 O2'
_chemical_formula_sum            'C19 H15 Br Cl3 N3 O2'
_chemical_formula_weight         503.60
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.0080(15)
_cell_length_b                   11.572(2)
_cell_length_c                   12.746(3)
_cell_angle_alpha                108.887(14)
_cell_angle_beta                 100.654(15)
_cell_angle_gamma                106.117(14)
_cell_volume                     1023.4(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8606
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.537
_cell_measurement_theta_min      3.845
_shelx_estimated_absorpt_T_max   0.562
_shelx_estimated_absorpt_T_min   0.245
_exptl_absorpt_coefficient_mu    6.520
_exptl_absorpt_correction_T_max  10
_exptl_absorpt_correction_T_min  1
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8606
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         69.537
_diffrn_reflns_theta_min         3.845
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2900
_reflns_number_total             3633
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.980
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3633
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      0.965
_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)+(0.0759P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1120
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H10(0.026) H12(0.03) H13(0.033) H15(0.034) H16(0.031) H17(0.026)
 H7(0.031) H2(0.03) H5(0.024) H19A(0.071) H19B(0.071) H19C(0.071) H9A(0.057)
 H9B(0.057) H9C(0.057)
 Fixed X: H10(0.410569) H12(0.034849) H13(-0.22662) H15(0.000609) H16(0.26208)
 H17(0.42079) H7(0.324221) H2(0.21851) H5(0.268821) H19A(0.860801)
 H19B(0.979679) H19C(0.91216) H9A(0.26171) H9B(0.367361) H9C(0.472729)
 Fixed Y: H10(0.168121) H12(0.27115) H13(0.168941) H15(-0.07336) H16(0.028841)
 H17(0.405809) H7(0.2185) H2(0.60492) H5(0.50281) H19A(0.618641) H19B(0.59809)
 H19C(0.71628) H9A(0.07316) H9B(0.07889) H9C(0.150331)
 Fixed Z: H10(0.736468) H12(0.74874) H13(0.786549) H15(0.86497) H16(0.827161)
 H17(0.904989) H7(0.358291) H2(0.39081) H5(0.71577) H19A(0.83393) H19B(0.93382)
 H19C(0.96355) H9A(0.45) H9B(0.569221) H9C(0.50232)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.35184(5) -0.04558(4) 0.86084(4) 0.04070(16) Uani 1 1 d . . . . .
Cl2 Cl 0.20460(11) 0.73631(8) 0.77976(7) 0.0260(2) Uani 1 1 d . . . . .
Cl1 Cl 0.17144(12) 0.80653(9) 0.55994(8) 0.0339(2) Uani 1 1 d . . . . .
Cl3 Cl 0.56008(11) 0.29359(9) 0.98820(7) 0.0305(2) Uani 1 1 d . . . . .
O2 O 0.7217(3) 0.3683(2) 0.7859(2) 0.0312(6) Uani 1 1 d . . . . .
O1 O 0.7171(3) 0.5454(2) 0.9247(2) 0.0346(6) Uani 1 1 d . . . . .
N2 N 0.3038(3) 0.3236(3) 0.5163(2) 0.0206(6) Uani 1 1 d . . . . .
N1 N 0.3170(3) 0.2933(3) 0.6848(2) 0.0207(6) Uani 1 1 d . . . . .
N3 N 0.2803(4) 0.3773(3) 0.3604(2) 0.0276(6) Uani 1 1 d . . . . .
C10 C 0.3514(4) 0.2303(3) 0.7656(3) 0.0219(7) Uani 1 1 d . . . . .
H10 H 0.410569 0.168121 0.736468 0.026 Uiso 1 1 d . . . . .
C11 C 0.1758(4) 0.1610(3) 0.7845(3) 0.0211(6) Uani 1 1 d . . . . .
C12 C 0.0267(5) 0.2012(3) 0.7724(3) 0.0256(7) Uani 1 1 d . . . . .
H12 H 0.034849 0.271150 0.748740 0.030 Uiso 1 1 d . . . . .
C13 C -0.1290(4) 0.1403(3) 0.7941(3) 0.0278(7) Uani 1 1 d . . . . .
H13 H -0.226620 0.168941 0.786549 0.033 Uiso 1 1 d . . . . .
C14 C -0.1366(4) 0.0389(3) 0.8298(3) 0.0261(7) Uani 1 1 d . . . . .
C15 C 0.0067(5) -0.0044(3) 0.8419(3) 0.0291(8) Uani 1 1 d . . . . .
H15 H 0.000609 -0.073360 0.864970 0.034 Uiso 1 1 d . . . . .
C16 C 0.1626(5) 0.0564(3) 0.8183(3) 0.0266(7) Uani 1 1 d . . . . .
H16 H 0.262080 0.028841 0.827161 0.031 Uiso 1 1 d . . . . .
C17 C 0.4823(4) 0.3454(3) 0.8764(3) 0.0218(6) Uani 1 1 d . . . . .
H17 H 0.420790 0.405809 0.904989 0.026 Uiso 1 1 d . . . . .
C7 C 0.3058(4) 0.2934(3) 0.4018(3) 0.0258(7) Uani 1 1 d . . . . .
H7 H 0.324221 0.218500 0.358291 0.031 Uiso 1 1 d . . . . .
C8 C 0.3274(4) 0.2483(3) 0.5832(3) 0.0200(6) Uani 1 1 d . . . . .
C2 C 0.2283(4) 0.5853(3) 0.4539(3) 0.0252(7) Uani 1 1 d . . . . .
H2 H 0.218510 0.604920 0.390810 0.030 Uiso 1 1 d . . . . .
C1 C 0.2129(4) 0.6652(3) 0.5552(3) 0.0242(7) Uani 1 1 d . . . . .
C6 C 0.2280(4) 0.6346(3) 0.6540(3) 0.0219(7) Uani 1 1 d . . . . .
C5 C 0.2596(4) 0.5225(3) 0.6531(3) 0.0199(6) Uani 1 1 d . . . . .
H5 H 0.268821 0.502810 0.715770 0.024 Uiso 1 1 d . . . . .
C4 C 0.2740(4) 0.4424(3) 0.5508(3) 0.0202(6) Uani 1 1 d . . . . .
C3 C 0.2593(4) 0.4730(3) 0.4521(3) 0.0230(7) Uani 1 1 d . . . . .
C18 C 0.6541(4) 0.4188(3) 0.8554(3) 0.0234(7) Uani 1 1 d . . . . .
C19 C 0.8818(6) 0.6265(4) 0.9130(3) 0.0474(11) Uani 1 1 d . . . . .
H19A H 0.860801 0.618641 0.833930 0.071 Uiso 1 1 d . . . . .
H19B H 0.979679 0.598090 0.933820 0.071 Uiso 1 1 d . . . . .
H19C H 0.912160 0.716280 0.963550 0.071 Uiso 1 1 d . . . . .
C9 C 0.3605(6) 0.1269(4) 0.5207(3) 0.0387(9) Uani 1 1 d . . . . .
H9A H 0.261710 0.073160 0.450000 0.057 Uiso 1 1 d . . . . .
H9B H 0.367361 0.078890 0.569221 0.057 Uiso 1 1 d . . . . .
H9C H 0.472729 0.150331 0.502320 0.057 Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C14 1.911(3) . ?
Cl2 C6 1.733(3) . ?
Cl1 C1 1.741(3) . ?
Cl3 C17 1.793(3) . ?
O2 C18 1.199(4) . ?
O1 C18 1.330(4) . ?
O1 C19 1.456(4) . ?
N2 C7 1.390(4) . ?
N2 C8 1.426(4) . ?
N2 C4 1.404(4) . ?
N1 C10 1.470(4) . ?
N1 C8 1.259(4) . ?
N3 C7 1.290(5) . ?
N3 C3 1.400(4) . ?
C10 C11 1.518(4) . ?
C10 C17 1.525(5) . ?
C11 C12 1.397(4) . ?
C11 C16 1.394(5) . ?
C12 C13 1.375(5) . ?
C13 C14 1.379(5) . ?
C14 C15 1.377(5) . ?
C15 C16 1.391(5) . ?
C17 C18 1.523(4) . ?
C8 C9 1.496(5) . ?
C2 C1 1.374(5) . ?
C2 C3 1.383(5) . ?
C1 C6 1.409(5) . ?
C6 C5 1.385(5) . ?
C5 C4 1.380(4) . ?
C4 C3 1.407(4) . ?

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
C18 O1 C19 115.8(3) . . ?
C7 N2 C8 126.6(3) . . ?
C7 N2 C4 105.5(3) . . ?
C4 N2 C8 127.9(3) . . ?
C8 N1 C10 121.1(3) . . ?
C7 N3 C3 104.4(3) . . ?
N1 C10 C11 111.1(3) . . ?
N1 C10 C17 102.9(3) . . ?
C11 C10 C17 112.0(3) . . ?
C12 C11 C10 121.9(3) . . ?
C16 C11 C10 119.8(3) . . ?
C16 C11 C12 118.3(3) . . ?
C13 C12 C11 121.2(3) . . ?
C12 C13 C14 119.2(3) . . ?
C13 C14 Br1 119.5(2) . . ?
C15 C14 Br1 119.0(3) . . ?
C15 C14 C13 121.5(3) . . ?
C14 C15 C16 118.9(3) . . ?
C15 C16 C11 120.9(3) . . ?
C10 C17 Cl3 112.1(2) . . ?
C18 C17 Cl3 105.4(2) . . ?
C18 C17 C10 111.7(3) . . ?
N3 C7 N2 114.7(3) . . ?
N2 C8 C9 114.4(3) . . ?
N1 C8 N2 115.7(3) . . ?
N1 C8 C9 129.9(3) . . ?
C1 C2 C3 117.6(3) . . ?
C2 C1 Cl1 118.8(2) . . ?
C2 C1 C6 121.5(3) . . ?
C6 C1 Cl1 119.7(3) . . ?
C1 C6 Cl2 120.3(3) . . ?
C5 C6 Cl2 118.4(2) . . ?
C5 C6 C1 121.3(3) . . ?
C4 C5 C6 116.8(3) . . ?
N2 C4 C3 104.5(3) . . ?
C5 C4 N2 133.6(3) . . ?
C5 C4 C3 121.9(3) . . ?
N3 C3 C4 110.9(3) . . ?
C2 C3 N3 128.2(3) . . ?
C2 C3 C4 120.9(3) . . ?
O2 C18 O1 125.4(3) . . ?
O2 C18 C17 124.2(3) . . ?
O1 C18 C17 110.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
