# 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. 
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#######################################################################

data_20220722_0m
_database_code_depnum_ccdc_archive 'CCDC 2241694'
loop_
_audit_author_name
_audit_author_address
'xinyuan wang'
;ZheJiang Normal University
China
;
_audit_update_record             
;
2023-02-14 deposited with the CCDC.	2023-08-28 downloaded from the CCDC.
;
_audit_creation_date             2022-07-25
_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         'C10 H10 Cl N3 O2'
_chemical_formula_sum            'C10 H10 Cl N3 O2'
_chemical_formula_weight         239.66
_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 0.0033 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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.347(2)
_cell_length_b                   11.8842(11)
_cell_length_c                   9.4684(9)
_cell_angle_alpha                90
_cell_angle_beta                 111.351(3)
_cell_angle_gamma                90
_cell_volume                     2237.2(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2492
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      25.06
_cell_measurement_theta_min      2.76
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6294
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0977 before and 0.0529 after correction.
The Ratio of minimum to maximum transmission is 0.8446.
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    1.423
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.154
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9082
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.371
_diffrn_reflns_theta_min         3.324
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1519
_reflns_number_total             2050
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2050
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      1.029
_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)+(0.0590P)²+2.7329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1481
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C007(H00A,H00B), C00F(H00F,H00G)
1.b Aromatic/amide H refined with riding coordinates:
 C00B(H00C), C00C(H00D), C00D(H00E)
1.c Idealised Me refined as rotating group:
 C00G(H00H,H00I,H00J)
;
_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 0.93527(4) 0.51385(10) 0.83288(9) 0.0950(4) Uani 1 1 d . . . . .
N002 N 0.72341(10) 0.48523(17) 0.2434(2) 0.0522(5) Uani 1 1 d . . . . .
O003 O 0.57329(10) 0.6353(2) 0.0376(2) 0.0833(7) Uani 1 1 d . . . . .
O004 O 0.61378(11) 0.5869(2) 0.2805(2) 0.0890(8) Uani 1 1 d . . . . .
N005 N 0.71838(12) 0.37196(19) 0.2308(3) 0.0639(6) Uani 1 1 d . . . . .
N006 N 0.76232(13) 0.3270(2) 0.3523(3) 0.0682(7) Uani 1 1 d . . . . .
C007 C 0.67883(13) 0.5546(2) 0.1238(3) 0.0556(7) Uani 1 1 d . . . . .
H00A H 0.663372 0.512196 0.029757 0.067 Uiso 1 1 calc R U . . .
H00B H 0.703238 0.619776 0.109630 0.067 Uiso 1 1 calc R U . . .
C008 C 0.61908(13) 0.5930(2) 0.1595(3) 0.0592(7) Uani 1 1 d . . . . .
C009 C 0.77175(12) 0.5145(2) 0.3778(3) 0.0495(6) Uani 1 1 d . . . . .
C00A C 0.79639(13) 0.4125(2) 0.4467(3) 0.0550(6) Uani 1 1 d . . . . .
C00B C 0.79638(14) 0.6176(2) 0.4453(3) 0.0585(7) Uani 1 1 d . . . . .
H00C H 0.779602 0.685629 0.398013 0.070 Uiso 1 1 calc R U . . .
C00C C 0.84687(14) 0.6131(3) 0.5856(3) 0.0656(8) Uani 1 1 d . . . . .
H00D H 0.864971 0.679538 0.635690 0.079 Uiso 1 1 calc R U . . .
C00D C 0.84778(14) 0.4090(3) 0.5897(3) 0.0640(8) Uani 1 1 d . . . . .
H00E H 0.864746 0.341299 0.637848 0.077 Uiso 1 1 calc R U . . .
C00E C 0.87144(14) 0.5096(3) 0.6542(3) 0.0640(8) Uani 1 1 d . . . . .
C00F C 0.50997(19) 0.6723(4) 0.0523(4) 0.1133(16) Uani 1 1 d . . . . .
H00F H 0.493801 0.614056 0.102371 0.136 Uiso 1 1 calc R U . . .
H00G H 0.518051 0.739672 0.114179 0.136 Uiso 1 1 calc R U . . .
C00G C 0.46185(19) 0.6941(5) -0.0888(5) 0.1286(17) Uani 1 1 d . . . . .
H00H H 0.456561 0.629238 -0.152578 0.193 Uiso 1 1 calc R U . . .
H00I H 0.475774 0.757149 -0.133618 0.193 Uiso 1 1 calc R U . . .
H00J H 0.419788 0.711063 -0.078345 0.193 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 C00E 1.744(3) . ?
N002 N005 1.352(3) . ?
N002 C007 1.443(3) . ?
N002 C009 1.360(3) . ?
O003 C008 1.311(3) . ?
O003 C00F 1.475(4) . ?
O004 C008 1.194(3) . ?
N005 N006 1.305(3) . ?
N006 C00A 1.374(4) . ?
C007 H00A 0.9700 . ?
C007 H00B 0.9700 . ?
C007 C008 1.504(4) . ?
C009 C00A 1.386(4) . ?
C009 C00B 1.393(4) . ?
C00A C00D 1.399(4) . ?
C00B H00C 0.9300 . ?
C00B C00C 1.374(4) . ?
C00C H00D 0.9300 . ?
C00C C00E 1.400(4) . ?
C00D H00E 0.9300 . ?
C00D C00E 1.354(4) . ?
C00F H00F 0.9700 . ?
C00F H00G 0.9700 . ?
C00F C00G 1.382(5) . ?
C00G H00H 0.9600 . ?
C00G H00I 0.9600 . ?
C00G H00J 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N005 N002 C007 119.4(2) . . ?
N005 N002 C009 110.2(2) . . ?
C009 N002 C007 130.3(2) . . ?
C008 O003 C00F 116.5(2) . . ?
N006 N005 N002 108.8(2) . . ?
N005 N006 C00A 108.1(2) . . ?
N002 C007 H00A 109.3 . . ?
N002 C007 H00B 109.3 . . ?
N002 C007 C008 111.6(2) . . ?
H00A C007 H00B 108.0 . . ?
C008 C007 H00A 109.3 . . ?
C008 C007 H00B 109.3 . . ?
O003 C008 C007 109.9(2) . . ?
O004 C008 O003 124.5(3) . . ?
O004 C008 C007 125.6(2) . . ?
N002 C009 C00A 104.2(2) . . ?
N002 C009 C00B 133.2(2) . . ?
C00A C009 C00B 122.6(2) . . ?
N006 C00A C009 108.7(2) . . ?
N006 C00A C00D 130.6(3) . . ?
C009 C00A C00D 120.8(3) . . ?
C009 C00B H00C 121.9 . . ?
C00C C00B C009 116.2(3) . . ?
C00C C00B H00C 121.9 . . ?
C00B C00C H00D 119.6 . . ?
C00B C00C C00E 120.9(3) . . ?
C00E C00C H00D 119.6 . . ?
C00A C00D H00E 121.9 . . ?
C00E C00D C00A 116.2(3) . . ?
C00E C00D H00E 121.9 . . ?
C00C C00E Cl01 116.9(2) . . ?
C00D C00E Cl01 119.6(2) . . ?
C00D C00E C00C 123.5(3) . . ?
O003 C00F H00F 109.6 . . ?
O003 C00F H00G 109.6 . . ?
H00F C00F H00G 108.1 . . ?
C00G C00F O003 110.4(3) . . ?
C00G C00F H00F 109.6 . . ?
C00G C00F H00G 109.6 . . ?
C00F C00G H00H 109.5 . . ?
C00F C00G H00I 109.5 . . ?
C00F C00G H00J 109.5 . . ?
H00H C00G H00I 109.5 . . ?
H00H C00G H00J 109.5 . . ?
H00I C00G H00J 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
N002 N005 N006 C00A 0.5(3) . . . . ?
N002 C007 C008 O003 -167.0(2) . . . . ?
N002 C007 C008 O004 13.4(4) . . . . ?
N002 C009 C00A N006 0.0(3) . . . . ?
N002 C009 C00A C00D 180.0(2) . . . . ?
N002 C009 C00B C00C -179.8(3) . . . . ?
N005 N002 C007 C008 96.7(3) . . . . ?
N005 N002 C009 C00A 0.3(3) . . . . ?
N005 N002 C009 C00B -180.0(3) . . . . ?
N005 N006 C00A C009 -0.3(3) . . . . ?
N005 N006 C00A C00D 179.7(3) . . . . ?
N006 C00A C00D C00E 179.7(3) . . . . ?
C007 N002 N005 N006 -178.8(2) . . . . ?
C007 N002 C009 C00A 178.3(2) . . . . ?
C007 N002 C009 C00B -2.0(5) . . . . ?
C008 O003 C00F C00G -168.3(4) . . . . ?
C009 N002 N005 N006 -0.5(3) . . . . ?
C009 N002 C007 C008 -81.1(3) . . . . ?
C009 C00A C00D C00E -0.3(4) . . . . ?
C009 C00B C00C C00E 0.2(4) . . . . ?
C00A C009 C00B C00C -0.2(4) . . . . ?
C00A C00D C00E Cl01 179.7(2) . . . . ?
C00A C00D C00E C00C 0.4(4) . . . . ?
C00B C009 C00A N006 -179.8(2) . . . . ?
C00B C009 C00A C00D 0.2(4) . . . . ?
C00B C00C C00E Cl01 -179.7(2) . . . . ?
C00B C00C C00E C00D -0.3(5) . . . . ?
C00F O003 C008 O004 -3.1(5) . . . . ?
C00F O003 C008 C007 177.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
