# Electronic Supplementary Material (ESI) for Inorganic 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_3_1zncl_auto
_database_code_depnum_ccdc_archive 'CCDC 2243044'
loop_
_audit_author_name
_audit_author_address
'Yaoguo Shen'
;Minjiang University
China
;
_audit_update_record             
;
2023-02-19 deposited with the CCDC.	2023-04-13 downloaded from the CCDC.
;
_audit_creation_date             2022-10-17
_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 H8 N O2, Cl, H2 O'
_chemical_formula_sum            'C10 H10 Cl N O3'
_chemical_formula_weight         227.64
_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                   10.6630(10)
_cell_length_b                   13.7778(16)
_cell_length_c                   7.2187(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.204(10)
_cell_angle_gamma                90
_cell_volume                     1054.31(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3762
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.9780
_cell_measurement_theta_min      1.9020
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.873
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6769
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.017
_diffrn_reflns_theta_min         1.921
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -80.00  35.00   0.50    3.32    --    9.30 -77.00-180.00  230
  2  ω    -16.00  99.00   0.50    3.32    --    9.30  77.00 -90.00  230
  3  ω    -16.00  99.00   0.50    3.32    --    9.30  77.00  60.00  230
  4  ω    -80.00 -55.00   0.50    3.32    --    9.30 -57.00   0.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Pro II AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0383826000
_diffrn_orient_matrix_UB_12      -0.0352910000
_diffrn_orient_matrix_UB_13      0.0501485000
_diffrn_orient_matrix_UB_21      -0.0496529000
_diffrn_orient_matrix_UB_22      -0.0343405000
_diffrn_orient_matrix_UB_23      -0.0152206000
_diffrn_orient_matrix_UB_31      0.0233630000
_diffrn_orient_matrix_UB_32      -0.0148534000
_diffrn_orient_matrix_UB_33      -0.0838267000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed 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                1738
_reflns_number_total             2185
_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 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2185
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.115
_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)+(0.0531P)²+0.0910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1124
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 O3-H3A = O3-H3B
 0.85 with sigma of 0.02
 H3A-H3B
 1.34 with sigma of 0.04
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9)
3.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.67012(4) 0.41561(3) -0.20708(6) 0.0511(2) Uani 1 1 d . . . . .
O1 O 0.34686(12) 0.30833(10) 0.19212(17) 0.0580(4) Uani 1 1 d . . . . .
O2 O 0.51114(11) 0.37161(10) 0.37025(17) 0.0546(4) Uani 1 1 d . . . . .
H2 H 0.552349 0.347482 0.292449 0.082 Uiso 1 1 calc R U . . .
N1 N 0.38362(15) 0.40932(10) 0.6410(2) 0.0407(4) Uani 1 1 d . . . . .
H1 H 0.466(2) 0.4052(13) 0.642(3) 0.060(6) Uiso 1 1 d . . . . .
C1 C 0.31596(15) 0.37975(11) 0.4855(2) 0.0370(4) Uani 1 1 d . . . . .
C2 C 0.18301(15) 0.37472(11) 0.4796(2) 0.0400(4) Uani 1 1 d . . . . .
C3 C 0.10223(16) 0.34602(13) 0.3190(3) 0.0521(5) Uani 1 1 d . . . . .
H3 H 0.136260 0.328937 0.210247 0.062 Uiso 1 1 calc R U . . .
C4 C -0.02502(18) 0.34361(15) 0.3249(3) 0.0628(6) Uani 1 1 d . . . . .
H4 H -0.077186 0.325290 0.219027 0.075 Uiso 1 1 calc R U . . .
C5 C -0.07874(18) 0.36818(14) 0.4870(3) 0.0613(6) Uani 1 1 d . . . . .
H5 H -0.165804 0.365178 0.487961 0.074 Uiso 1 1 calc R U . . .
C6 C -0.00522(18) 0.39632(14) 0.6429(3) 0.0556(5) Uani 1 1 d . . . . .
H6 H -0.042243 0.412672 0.749555 0.067 Uiso 1 1 calc R U . . .
C7 C 0.12812(16) 0.40097(12) 0.6442(3) 0.0451(4) Uani 1 1 d . . . . .
C8 C 0.20676(19) 0.43110(13) 0.8018(3) 0.0526(5) Uani 1 1 d . . . . .
H8 H 0.171719 0.448626 0.909488 0.063 Uiso 1 1 calc R U . . .
C9 C 0.33350(18) 0.43490(13) 0.7985(3) 0.0493(5) Uani 1 1 d . . . . .
H9 H 0.385508 0.454874 0.903291 0.059 Uiso 1 1 calc R U . . .
C10 C 0.39143(16) 0.34911(12) 0.3303(2) 0.0417(4) Uani 1 1 d . . . . .
O3 O 0.66551(13) 0.30320(10) 0.16429(19) 0.0552(4) Uani 1 1 d D . . . .
H3A H 0.659(2) 0.3250(16) 0.055(2) 0.083 Uiso 1 1 d D U . . .
H3B H 0.665(2) 0.2422(11) 0.165(3) 0.083 Uiso 1 1 d D 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
O1 C10 1.197(2) . ?
O2 H2 0.8200 . ?
O2 C10 1.315(2) . ?
N1 H1 0.88(2) . ?
N1 C1 1.331(2) . ?
N1 C9 1.354(2) . ?
C1 C2 1.415(2) . ?
C1 C10 1.509(2) . ?
C2 C3 1.424(2) . ?
C2 C7 1.427(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.362(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.399(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.357(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.422(2) . ?
C7 C8 1.401(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.355(3) . ?
C9 H9 0.9300 . ?
O3 H3A 0.841(15) . ?
O3 H3B 0.841(15) . ?

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
C10 O2 H2 109.5 . . ?
C1 N1 H1 116.1(14) . . ?
C1 N1 C9 124.09(15) . . ?
C9 N1 H1 119.5(14) . . ?
N1 C1 C2 119.36(16) . . ?
N1 C1 C10 115.34(14) . . ?
C2 C1 C10 125.22(15) . . ?
C1 C2 C3 123.64(17) . . ?
C1 C2 C7 117.53(15) . . ?
C3 C2 C7 118.83(16) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.89(19) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.3(2) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.73(18) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.41(19) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C2 118.86(18) . . ?
C8 C7 C2 119.20(16) . . ?
C8 C7 C6 121.94(18) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.50(17) . . ?
C9 C8 H8 119.7 . . ?
N1 C9 C8 119.31(18) . . ?
N1 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
O1 C10 O2 125.60(16) . . ?
O1 C10 C1 123.67(15) . . ?
O2 C10 C1 110.72(15) . . ?
H3A O3 H3B 111(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O3 0.82 1.71 2.5174(18) 167.6 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 178.63(15) . . . . ?
N1 C1 C2 C7 -0.8(2) . . . . ?
N1 C1 C10 O1 169.25(16) . . . . ?
N1 C1 C10 O2 -9.5(2) . . . . ?
C1 N1 C9 C8 -0.2(3) . . . . ?
C1 C2 C3 C4 -179.67(18) . . . . ?
C1 C2 C7 C6 -179.77(15) . . . . ?
C1 C2 C7 C8 0.6(2) . . . . ?
C2 C1 C10 O1 -7.6(3) . . . . ?
C2 C1 C10 O2 173.66(16) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C2 C7 C8 C9 -0.3(3) . . . . ?
C3 C2 C7 C6 0.8(2) . . . . ?
C3 C2 C7 C8 -178.78(16) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C2 -0.6(3) . . . . ?
C5 C6 C7 C8 179.02(18) . . . . ?
C6 C7 C8 C9 -179.88(18) . . . . ?
C7 C2 C3 C4 -0.3(3) . . . . ?
C7 C8 C9 N1 0.1(3) . . . . ?
C9 N1 C1 C2 0.5(2) . . . . ?
C9 N1 C1 C10 -176.50(15) . . . . ?
C10 C1 C2 C3 -4.6(3) . . . . ?
C10 C1 C2 C7 175.98(15) . . . . ?

_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 3.632
_oxdiff_exptl_absorpt_empirical_full_min 0.322
