# Supplementary Information (SI) for Chemical Science.
# 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. 
# 
#######################################################################

data_form_I
_database_code_depnum_ccdc_archive 'CCDC 2376850'
loop_
_audit_author_name
_audit_author_address
'Jiaxuan Zhu'
;The Cambridge crystallographic data centre
China
;
_audit_update_record             
;
2024-08-24 deposited with the CCDC.	2024-10-22 downloaded from the CCDC.
;
_audit_creation_date             2024-04-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 Cl N3 O'
_chemical_formula_sum            'C16 H16 Cl N3 O'
_chemical_formula_weight         301.77
_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'
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                   5.2898(2)
_cell_length_b                   7.8669(3)
_cell_length_c                   17.5590(6)
_cell_angle_alpha                99.161(3)
_cell_angle_beta                 96.187(3)
_cell_angle_gamma                90.692(3)
_cell_volume                     716.87(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4635
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      71.7470
_cell_measurement_theta_min      2.5870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.375
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5886
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.149
_diffrn_reflns_theta_min         2.565
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     37.00  81.00   0.50    0.05    --   36.12-143.00 -30.00   88
  2  ω     93.00 120.00   0.50    0.05    --  108.45-143.00 -30.00   54
  3  ω     39.00  98.00   0.50    0.05    --   36.12-127.00 138.00  118
  4  ω     83.00 111.00   0.50    0.05    --  108.45-127.00 138.00   56
  5  ω     30.00  74.00   0.50    0.05    --  108.45-127.00 138.00   88
  6  ω     39.00  64.00   0.50    0.05    --  108.45 -61.00 150.00   50
  7  ω     41.00  81.00   0.50    0.05    --  108.45 -77.00  30.00   80
  8  ω     32.00  86.00   0.50    0.05    --  108.45 -77.00-150.00  108
  9  ω     50.00 103.00   0.50    0.05    --  108.45 -77.00 -90.00  106
 10  ω     49.00  75.00   0.50    0.05    --  108.45 -77.00 -60.00   52
 11  ω     -2.00 115.00   0.50    0.05    --   36.12  37.00 150.00  234
 12  ω     98.00 123.00   0.50    0.05    --  108.45 143.00  24.00   50
 13  ω    113.00 144.00   0.50    0.05    --  108.45 179.00 -30.00   62
 14  ω    118.00 145.00   0.50    0.05    --  108.45 179.00-120.00   54
 15  ω     77.00 105.00   0.50    0.05    --  108.45 127.00-145.00   56
 16  ω     45.00  77.00   0.50    0.05    --  108.45 179.00-120.00   64
 17  ω     53.00  97.00   0.50    0.05    --  108.45 179.00 -30.00   88
 18  ω    130.00 169.00   0.50    0.05    --  108.45 111.00  90.00   78
 19  ω     88.00 117.00   0.50    0.05    --  108.45 111.00  90.00   58
 20  ω    -42.00  22.00   0.50    0.05    --   36.12 -19.00 -30.00  128
 21  ω    -43.00  17.00   0.50    0.05    --   36.12 -19.00-150.00  120
 22  ω    -50.00 -15.00   0.50    0.05    --   36.12 -19.00-180.00   70
 23  ω   -151.00-124.00   0.50    0.05    -- -100.00 -94.00 -90.00   54
 24  ω   -116.00 -88.00   0.50    0.05    -- -100.00 -94.00 -90.00   56
 25  ω   -125.00 -74.00   0.50    0.05    --  -36.12-179.00  60.00  102
 26  ω   -101.00 -70.00   0.50    0.05    -- -100.00-143.00 -30.00   62
 27  ω   -171.00 -68.00   0.50    0.05    -- -100.00 -61.00  60.00  206
 28  ω   -163.00 -68.00   0.50    0.05    -- -100.00 -61.00  30.00  190
 29  ω   -151.00-126.00   0.50    0.05    -- -100.00-127.00 138.00   50
 30  ω    -54.00 -20.00   0.50    0.05    -- -100.00  45.00 -30.00   68
 31  ω    -53.00 -20.00   0.50    0.05    -- -100.00  45.00  30.00   66
 32  ω    -52.00 -21.00   0.50    0.05    -- -100.00  45.00   0.00   62
 33  ω   -102.00 -55.00   0.50    0.05    -- -100.00  77.00-150.00   94
 34  ω    -54.00 -19.00   0.50    0.05    -- -100.00  45.00-180.00   70
 35  ω    -46.00 -21.00   0.50    0.05    -- -100.00  77.00-150.00   50
 36  ω    -64.00 -31.00   0.50    0.05    -- -100.00 127.00-145.00   66
 37  ω    -88.00 -54.00   0.50    0.05    -- -100.00 179.00 -90.00   68
 38  ω   -150.00 -92.00   0.50    0.05    -- -100.00 179.00 -90.00  116
 39  ω   -120.00 -68.00   0.50    0.05    -- -100.00 143.00  24.00  104
 40  ω   -108.00 -48.00   0.50    0.05    -- -100.00 179.00  30.00  120
 41  ω    -95.00 -70.00   0.50    0.05    --  -36.12 143.00  24.00   50
 42  ω    -77.00 -50.00   0.50    0.05    --  -36.12 127.00-145.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0092387000
_diffrn_orient_matrix_UB_12      0.0268948000
_diffrn_orient_matrix_UB_13      0.0891118000
_diffrn_orient_matrix_UB_21      -0.1452695000
_diffrn_orient_matrix_UB_22      -0.1731899000
_diffrn_orient_matrix_UB_23      -0.0054478000
_diffrn_orient_matrix_UB_31      0.2543651000
_diffrn_orient_matrix_UB_32      -0.0930758000
_diffrn_orient_matrix_UB_33      0.0051009000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2481
_reflns_number_total             2655
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.079
_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)+(0.0676P)²+0.1778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1059
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N003(H003), C007(H007), C009(H009), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00H(H00H), C00I(H00I), C00J(H00J)
2.b Idealised Me refined as rotating group:
 C00K(H00A,H00F,H00G), C00L(H00K,H00L,H00M)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl01 Cl 0.04434(7) 0.91069(4) 0.10013(2) 0.02569(15) Uani 1 1 d . . . . .
O002 O -0.23773(19) 0.78059(14) 0.44882(6) 0.0255(3) Uani 1 1 d . . . . .
N003 N 0.1944(2) 0.76549(15) 0.46938(7) 0.0198(3) Uani 1 1 d . . . . .
H003 H 0.338775 0.764651 0.448673 0.024 Uiso 1 1 calc R U . . .
N004 N 0.1937(2) 0.74344(15) 0.54596(7) 0.0205(3) Uani 1 1 d . . . . .
N005 N 0.5382(2) 0.62613(15) 0.89686(7) 0.0211(3) Uani 1 1 d . . . . .
C006 C 0.4349(3) 0.67323(17) 0.65864(8) 0.0176(3) Uani 1 1 d . . . . .
C007 C 0.6815(3) 0.57312(17) 0.76688(8) 0.0190(3) Uani 1 1 d . . . . .
H007 H 0.824463 0.513683 0.785630 0.023 Uiso 1 1 calc R U . . .
C008 C 0.5096(3) 0.64275(17) 0.81816(8) 0.0179(3) Uani 1 1 d . . . . .
C009 C 0.4037(3) 0.69271(17) 0.57683(8) 0.0193(3) Uani 1 1 d . . . . .
H009 H 0.540443 0.667529 0.546308 0.023 Uiso 1 1 calc R U . . .
C00A C 0.0031(3) 0.81967(17) 0.34566(8) 0.0178(3) Uani 1 1 d . . . . .
C00B C 0.2620(3) 0.74139(17) 0.70967(8) 0.0187(3) Uani 1 1 d . . . . .
H00B H 0.116866 0.797984 0.690385 0.022 Uiso 1 1 calc R U . . .
C00C C -0.1868(3) 0.75254(18) 0.28690(8) 0.0202(3) Uani 1 1 d . . . . .
H00C H -0.326428 0.688581 0.298994 0.024 Uiso 1 1 calc R U . . .
C00D C 0.2078(3) 0.91426(18) 0.32789(8) 0.0201(3) Uani 1 1 d . . . . .
H00D H 0.338816 0.959244 0.367582 0.024 Uiso 1 1 calc R U . . .
C00E C 0.2987(3) 0.72779(18) 0.78728(8) 0.0189(3) Uani 1 1 d . . . . .
H00E H 0.179567 0.776668 0.820679 0.023 Uiso 1 1 calc R U . . .
C00F C -0.0271(3) 0.78839(18) 0.42624(8) 0.0194(3) Uani 1 1 d . . . . .
C00G C 0.0297(3) 0.87380(17) 0.19529(8) 0.0190(3) Uani 1 1 d . . . . .
C00H C 0.6448(3) 0.59030(17) 0.68902(8) 0.0185(3) Uani 1 1 d . . . . .
H00H H 0.765659 0.544388 0.655607 0.022 Uiso 1 1 calc R U . . .
C00I C -0.1746(3) 0.77791(18) 0.21111(8) 0.0215(3) Uani 1 1 d . . . . .
H00I H -0.302876 0.730845 0.170943 0.026 Uiso 1 1 calc R U . . .
C00J C 0.2202(3) 0.94265(18) 0.25229(9) 0.0205(3) Uani 1 1 d . . . . .
H00J H 0.357515 1.008418 0.239985 0.025 Uiso 1 1 calc R U . . .
C00K C 0.4655(3) 0.7719(2) 0.95158(9) 0.0263(3) Uani 1 1 d . . . . .
H00A H 0.574770 0.872445 0.949954 0.039 Uiso 1 1 calc R U . . .
H00F H 0.485158 0.742924 1.004107 0.039 Uiso 1 1 calc R U . . .
H00G H 0.287658 0.798294 0.937445 0.039 Uiso 1 1 calc R U . . .
C00L C 0.7677(3) 0.5473(2) 0.92599(9) 0.0316(4) Uani 1 1 d . . . . .
H00K H 0.781194 0.432556 0.895609 0.047 Uiso 1 1 calc R U . . .
H00L H 0.760630 0.536961 0.980613 0.047 Uiso 1 1 calc R U . . .
H00M H 0.916333 0.619009 0.921409 0.047 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 C00G 1.7505(14) . ?
O002 C00F 1.2260(18) . ?
N003 H003 0.8800 . ?
N003 N004 1.3833(16) . ?
N003 C00F 1.3554(19) . ?
N004 C009 1.2798(19) . ?
N005 C008 1.4009(18) . ?
N005 C00K 1.4578(19) . ?
N005 C00L 1.451(2) . ?
C006 C009 1.4608(19) . ?
C006 C00B 1.401(2) . ?
C006 C00H 1.394(2) . ?
C007 H007 0.9500 . ?
C007 C008 1.404(2) . ?
C007 C00H 1.388(2) . ?
C008 C00E 1.410(2) . ?
C009 H009 0.9500 . ?
C00A C00C 1.394(2) . ?
C00A C00D 1.397(2) . ?
C00A C00F 1.4990(19) . ?
C00B H00B 0.9500 . ?
C00B C00E 1.377(2) . ?
C00C H00C 0.9500 . ?
C00C C00I 1.385(2) . ?
C00D H00D 0.9500 . ?
C00D C00J 1.389(2) . ?
C00E H00E 0.9500 . ?
C00G C00I 1.388(2) . ?
C00G C00J 1.381(2) . ?
C00H H00H 0.9500 . ?
C00I H00I 0.9500 . ?
C00J H00J 0.9500 . ?
C00K H00A 0.9800 . ?
C00K H00F 0.9800 . ?
C00K H00G 0.9800 . ?
C00L H00K 0.9800 . ?
C00L H00L 0.9800 . ?
C00L H00M 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
N004 N003 H003 120.0 . . ?
C00F N003 H003 120.0 . . ?
C00F N003 N004 120.00(11) . . ?
C009 N004 N003 114.55(12) . . ?
C008 N005 C00K 116.96(11) . . ?
C008 N005 C00L 117.31(12) . . ?
C00L N005 C00K 112.51(12) . . ?
C00B C006 C009 121.72(13) . . ?
C00H C006 C009 120.51(13) . . ?
C00H C006 C00B 117.73(13) . . ?
C008 C007 H007 119.7 . . ?
C00H C007 H007 119.7 . . ?
C00H C007 C008 120.62(13) . . ?
N005 C008 C007 122.33(13) . . ?
N005 C008 C00E 120.15(12) . . ?
C007 C008 C00E 117.50(13) . . ?
N004 C009 C006 120.50(13) . . ?
N004 C009 H009 119.7 . . ?
C006 C009 H009 119.7 . . ?
C00C C00A C00D 119.56(13) . . ?
C00C C00A C00F 117.33(12) . . ?
C00D C00A C00F 123.10(12) . . ?
C006 C00B H00B 119.4 . . ?
C00E C00B C006 121.16(13) . . ?
C00E C00B H00B 119.4 . . ?
C00A C00C H00C 119.6 . . ?
C00I C00C C00A 120.84(13) . . ?
C00I C00C H00C 119.6 . . ?
C00A C00D H00D 119.9 . . ?
C00J C00D C00A 120.10(13) . . ?
C00J C00D H00D 119.9 . . ?
C008 C00E H00E 119.3 . . ?
C00B C00E C008 121.31(13) . . ?
C00B C00E H00E 119.3 . . ?
O002 C00F N003 124.29(13) . . ?
O002 C00F C00A 121.38(13) . . ?
N003 C00F C00A 114.30(12) . . ?
C00I C00G Cl01 118.86(11) . . ?
C00J C00G Cl01 118.96(11) . . ?
C00J C00G C00I 122.18(13) . . ?
C006 C00H H00H 119.2 . . ?
C007 C00H C006 121.65(13) . . ?
C007 C00H H00H 119.2 . . ?
C00C C00I C00G 118.34(13) . . ?
C00C C00I H00I 120.8 . . ?
C00G C00I H00I 120.8 . . ?
C00D C00J H00J 120.5 . . ?
C00G C00J C00D 118.97(13) . . ?
C00G C00J H00J 120.5 . . ?
N005 C00K H00A 109.5 . . ?
N005 C00K H00F 109.5 . . ?
N005 C00K H00G 109.5 . . ?
H00A C00K H00F 109.5 . . ?
H00A C00K H00G 109.5 . . ?
H00F C00K H00G 109.5 . . ?
N005 C00L H00K 109.5 . . ?
N005 C00L H00L 109.5 . . ?
N005 C00L H00M 109.5 . . ?
H00K C00L H00L 109.5 . . ?
H00K C00L H00M 109.5 . . ?
H00L C00L H00M 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 C00G C00I C00C -178.70(10) . . . . ?
Cl01 C00G C00J C00D 179.62(10) . . . . ?
N003 N004 C009 C006 176.59(11) . . . . ?
N004 N003 C00F O002 -4.8(2) . . . . ?
N004 N003 C00F C00A 177.02(11) . . . . ?
N005 C008 C00E C00B -178.04(12) . . . . ?
C006 C00B C00E C008 -0.9(2) . . . . ?
C007 C008 C00E C00B 0.3(2) . . . . ?
C008 C007 C00H C006 -1.4(2) . . . . ?
C009 C006 C00B C00E -177.53(12) . . . . ?
C009 C006 C00H C007 178.69(12) . . . . ?
C00A C00C C00I C00G -0.9(2) . . . . ?
C00A C00D C00J C00G -1.0(2) . . . . ?
C00B C006 C009 N004 -13.4(2) . . . . ?
C00B C006 C00H C007 0.8(2) . . . . ?
C00C C00A C00D C00J 0.7(2) . . . . ?
C00C C00A C00F O002 -33.12(19) . . . . ?
C00C C00A C00F N003 145.14(13) . . . . ?
C00D C00A C00C C00I 0.2(2) . . . . ?
C00D C00A C00F O002 145.69(14) . . . . ?
C00D C00A C00F N003 -36.05(18) . . . . ?
C00F N003 N004 C009 168.13(13) . . . . ?
C00F C00A C00C C00I 179.10(12) . . . . ?
C00F C00A C00D C00J -178.09(12) . . . . ?
C00H C006 C009 N004 168.79(13) . . . . ?
C00H C006 C00B C00E 0.3(2) . . . . ?
C00H C007 C008 N005 179.12(12) . . . . ?
C00H C007 C008 C00E 0.8(2) . . . . ?
C00I C00G C00J C00D 0.4(2) . . . . ?
C00J C00G C00I C00C 0.5(2) . . . . ?
C00K N005 C008 C007 143.91(14) . . . . ?
C00K N005 C008 C00E -37.83(18) . . . . ?
C00L N005 C008 C007 5.7(2) . . . . ?
C00L N005 C008 C00E -176.08(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.880
_oxdiff_exptl_absorpt_empirical_full_min 0.567
####################################################################### 
# 
# 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_r20240420a
_database_code_depnum_ccdc_archive 'CCDC 2376851'
loop_
_audit_author_name
_audit_author_address
'Zhu jiaxuan'
;Tianjin University
China
;
_audit_update_record             
;
2024-08-11 deposited with the CCDC.	2024-10-22 downloaded from the CCDC.
;
_audit_creation_date             2024-04-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 Cl N3 O'
_chemical_formula_sum            'C16 H16 Cl N3 O'
_chemical_formula_weight         301.77
_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      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                   14.9184(5)
_cell_length_b                   12.9302(4)
_cell_length_c                   7.6631(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.635(3)
_cell_angle_gamma                90
_cell_volume                     1468.30(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4315
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      31.1650
_cell_measurement_theta_min      2.0770
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12460
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.554
_diffrn_reflns_theta_min         2.090
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -78.00  -8.00   1.00   35.00    --  -13.40 -57.00  30.00   70
  2  ω    -28.00  50.00   1.00   35.00    --  -13.40  38.00-150.00   78
  3  ω    -93.00  -3.00   1.00   35.00    --  -13.40 -57.00 120.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku MM007 Saturn944+'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0376945000
_diffrn_orient_matrix_UB_12      0.0336201000
_diffrn_orient_matrix_UB_13      -0.0144167000
_diffrn_orient_matrix_UB_21      -0.0294116000
_diffrn_orient_matrix_UB_22      -0.0424945000
_diffrn_orient_matrix_UB_23      0.0070336000
_diffrn_orient_matrix_UB_31      0.0019655000
_diffrn_orient_matrix_UB_32      0.0085088000
_diffrn_orient_matrix_UB_33      0.0918365000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3702
_reflns_number_total             4677
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         4677
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0643
_refine_ls_restrained_S_all      1.079
_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)+(0.0501P)²+0.6811P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1391
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.9 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14)
3.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_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
Cl1 Cl 0.19318(3) -0.08569(4) -0.01138(7) 0.03299(15) Uani 1 1 d . . . . .
O1 O -0.10691(8) -0.13854(9) -0.73851(15) 0.0184(3) Uani 1 1 d . . . . .
N1 N -0.17213(9) -0.22803(11) -0.52965(17) 0.0147(3) Uani 1 1 d D . . . .
H1 H -0.1631(13) -0.2638(14) -0.4292(18) 0.026(6) Uiso 1 1 d D . . . .
N2 N -0.24953(9) -0.24798(11) -0.64282(17) 0.0147(3) Uani 1 1 d . . . . .
N3 N -0.64152(10) -0.41377(12) -0.95984(19) 0.0202(3) Uani 1 1 d . . . . .
C1 C 0.10563(12) -0.10736(13) -0.1781(2) 0.0203(4) Uani 1 1 d . . . . .
C2 C 0.12649(12) -0.12634(14) -0.3466(3) 0.0220(4) Uani 1 1 d . . . . .
H2 H 0.187553 -0.127674 -0.370587 0.026 Uiso 1 1 calc R U . . .
C3 C 0.05669(11) -0.14343(13) -0.4803(2) 0.0184(3) Uani 1 1 d . . . . .
H3 H 0.069943 -0.155396 -0.596890 0.022 Uiso 1 1 calc R U . . .
C4 C -0.03271(11) -0.14303(12) -0.4434(2) 0.0144(3) Uani 1 1 d . . . . .
C5 C -0.05157(12) -0.12306(12) -0.2729(2) 0.0162(3) Uani 1 1 d . . . . .
H5 H -0.112512 -0.121468 -0.248143 0.019 Uiso 1 1 calc R U . . .
C6 C 0.01768(12) -0.10536(12) -0.1379(2) 0.0189(3) Uani 1 1 d . . . . .
H6 H 0.004775 -0.092275 -0.021404 0.023 Uiso 1 1 calc R U . . .
C7 C -0.10649(10) -0.16820(12) -0.5854(2) 0.0135(3) Uani 1 1 d . . . . .
C8 C -0.29814(10) -0.32240(12) -0.5934(2) 0.0139(3) Uani 1 1 d . . . . .
H8 H -0.276301 -0.362874 -0.494012 0.017 Uiso 1 1 calc R U . . .
C9 C -0.38636(10) -0.34517(12) -0.6883(2) 0.0135(3) Uani 1 1 d . . . . .
C10 C -0.43102(11) -0.27489(12) -0.8066(2) 0.0142(3) Uani 1 1 d . . . . .
H10 H -0.403363 -0.210242 -0.825136 0.017 Uiso 1 1 calc R U . . .
C11 C -0.51405(11) -0.29677(13) -0.8972(2) 0.0154(3) Uani 1 1 d . . . . .
H11 H -0.542197 -0.247526 -0.977727 0.018 Uiso 1 1 calc R U . . .
C12 C -0.55793(11) -0.39163(13) -0.8718(2) 0.0154(3) Uani 1 1 d . . . . .
C13 C -0.51328(11) -0.46196(13) -0.7510(2) 0.0180(3) Uani 1 1 d . . . . .
H13 H -0.540832 -0.526437 -0.730813 0.022 Uiso 1 1 calc R U . . .
C14 C -0.42992(11) -0.43852(13) -0.6613(2) 0.0166(3) Uani 1 1 d . . . . .
H14 H -0.401647 -0.486967 -0.579424 0.020 Uiso 1 1 calc R U . . .
C15 C -0.67865(12) -0.51742(14) -0.9453(3) 0.0234(4) Uani 1 1 d . . . . .
H15A H -0.634520 -0.568762 -0.974929 0.035 Uiso 1 1 calc R U . . .
H15B H -0.734130 -0.524159 -1.026423 0.035 Uiso 1 1 calc R U . . .
H15C H -0.692231 -0.528933 -0.824688 0.035 Uiso 1 1 calc R U . . .
C16 C -0.67758(12) -0.34895(16) -1.1054(2) 0.0251(4) Uani 1 1 d . . . . .
H16A H -0.685662 -0.278405 -1.063134 0.038 Uiso 1 1 calc R U . . .
H16B H -0.735920 -0.376470 -1.156828 0.038 Uiso 1 1 calc R U . . .
H16C H -0.635544 -0.348111 -1.194640 0.038 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 C1 1.7409(17) . ?
O1 C7 1.2335(19) . ?
N1 H1 0.895(9) . ?
N1 N2 1.3858(18) . ?
N1 C7 1.355(2) . ?
N2 C8 1.288(2) . ?
N3 C12 1.378(2) . ?
N3 C15 1.459(2) . ?
N3 C16 1.448(2) . ?
C1 C2 1.385(3) . ?
C1 C6 1.382(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.391(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(2) . ?
C4 C5 1.392(2) . ?
C4 C7 1.492(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(2) . ?
C6 H6 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.458(2) . ?
C9 C10 1.397(2) . ?
C9 C14 1.398(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.378(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.414(2) . ?
C12 C13 1.409(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(2) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
N2 N1 H1 118.3(13) . . ?
C7 N1 H1 121.6(13) . . ?
C7 N1 N2 119.27(13) . . ?
C8 N2 N1 114.31(13) . . ?
C12 N3 C15 118.91(15) . . ?
C12 N3 C16 119.44(14) . . ?
C16 N3 C15 118.68(14) . . ?
C2 C1 Cl1 118.85(14) . . ?
C6 C1 Cl1 118.98(14) . . ?
C6 C1 C2 122.17(16) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.01(16) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.13(16) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C7 119.56(15) . . ?
C5 C4 C3 119.51(15) . . ?
C5 C4 C7 120.88(14) . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.93(16) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.23(16) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
O1 C7 N1 123.58(14) . . ?
O1 C7 C4 123.25(14) . . ?
N1 C7 C4 113.17(13) . . ?
N2 C8 H8 119.7 . . ?
N2 C8 C9 120.70(14) . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 121.84(14) . . ?
C10 C9 C14 117.58(14) . . ?
C14 C9 C8 120.58(15) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.80(15) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.82(15) . . ?
C12 C11 H11 119.6 . . ?
N3 C12 C11 121.33(15) . . ?
N3 C12 C13 121.34(15) . . ?
C13 C12 C11 117.32(15) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 120.98(15) . . ?
C14 C13 H13 119.5 . . ?
C9 C14 H14 119.3 . . ?
C13 C14 C9 121.49(15) . . ?
C13 C14 H14 119.3 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C2 C3 -179.83(13) . . . . ?
Cl1 C1 C6 C5 -179.88(12) . . . . ?
N1 N2 C8 C9 173.27(13) . . . . ?
N2 N1 C7 O1 -7.9(2) . . . . ?
N2 N1 C7 C4 173.02(13) . . . . ?
N2 C8 C9 C10 -15.6(2) . . . . ?
N2 C8 C9 C14 165.40(15) . . . . ?
N3 C12 C13 C14 -179.07(15) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C2 C3 C4 C5 1.5(2) . . . . ?
C2 C3 C4 C7 -176.06(15) . . . . ?
C3 C4 C5 C6 -1.2(2) . . . . ?
C3 C4 C7 O1 -39.4(2) . . . . ?
C3 C4 C7 N1 139.74(15) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C5 C4 C7 O1 143.12(16) . . . . ?
C5 C4 C7 N1 -37.8(2) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C7 N1 N2 C8 165.56(14) . . . . ?
C7 C4 C5 C6 176.30(15) . . . . ?
C8 C9 C10 C11 179.52(14) . . . . ?
C8 C9 C14 C13 -179.49(15) . . . . ?
C9 C10 C11 C12 0.7(2) . . . . ?
C10 C9 C14 C13 1.5(2) . . . . ?
C10 C11 C12 N3 179.09(15) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
C11 C12 C13 C14 0.0(2) . . . . ?
C12 C13 C14 C9 -0.8(3) . . . . ?
C14 C9 C10 C11 -1.4(2) . . . . ?
C15 N3 C12 C11 172.54(15) . . . . ?
C15 N3 C12 C13 -8.4(2) . . . . ?
C16 N3 C12 C11 12.3(2) . . . . ?
C16 N3 C12 C13 -168.67(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.708
_oxdiff_exptl_absorpt_empirical_full_min 0.574
