# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_g210927a
_database_code_depnum_ccdc_archive 'CCDC 2159922'
loop_
_audit_author_name
_audit_author_address
quanyou
;Suzhou University
China
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2022-06-24 downloaded from the CCDC.
;
_audit_creation_date             2021-09-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H10 Cl N O3'
_chemical_formula_sum            'C10 H10 Cl N O3'
_chemical_formula_weight         227.64
_chemical_absolute_configuration S
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Cl'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.3826(10)
_cell_length_b                   11.4210(15)
_cell_length_c                   11.6800(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     984.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1028
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.4000
_cell_measurement_theta_min      5.4320
_shelx_estimated_absorpt_T_max   0.554
_shelx_estimated_absorpt_T_min   0.434
_exptl_absorpt_coefficient_mu    3.343
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2560
_diffrn_reflns_point_group_measured_fraction_full 0.868
_diffrn_reflns_point_group_measured_fraction_max 0.830
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.473
_diffrn_reflns_theta_min         5.417
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    3.00   33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9843   57.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega  -68.00  -28.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9843   57.0000   30.0000 40

#__ type_ start__ end____ width___ exp.time_
  3 omega  -47.00   12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9843   37.0000  150.0000 59

#__ type_ start__ end____ width___ exp.time_
  4 omega  -28.00   27.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9843   37.0000 -150.0000 55

#__ type_ start__ end____ width___ exp.time_
  5 omega  106.00  175.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000  150.0000 69

#__ type_ start__ end____ width___ exp.time_
  6 omega   45.00   95.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000  120.0000 50

#__ type_ start__ end____ width___ exp.time_
  7 omega   35.00  106.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000   90.0000 71

#__ type_ start__ end____ width___ exp.time_
  8 omega   40.00   87.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000 -120.0000 47

#__ type_ start__ end____ width___ exp.time_
  9 omega   36.00   85.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000  -30.0000 49
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1432808000
_diffrn_orient_matrix_UB_12      0.0833481000
_diffrn_orient_matrix_UB_13      -0.0506219000
_diffrn_orient_matrix_UB_21      0.1113313000
_diffrn_orient_matrix_UB_22      0.0098140000
_diffrn_orient_matrix_UB_23      -0.1108392000
_diffrn_orient_matrix_UB_31      -0.1028833000
_diffrn_orient_matrix_UB_32      -0.1056890000
_diffrn_orient_matrix_UB_33      -0.0504620000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.459
_reflns_Friedel_fraction_full    0.684
_reflns_Friedel_fraction_max     0.632
_reflns_number_gt                1473
_reflns_number_total             1744
_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, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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         0.549
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details 
;
 Flack x determined using 380 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1744
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0743
_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)+(0.1500P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2048
_refine_ls_wR_factor_ref         0.2192
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C6(H6), C8(H8), C5(H5)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 0.3939(3) 0.06991(14) 0.83141(13) 0.0651(5) Uani 1 1 d . . . . .
O2 O 0.4055(8) 0.4068(4) 0.2223(4) 0.0622(12) Uani 1 1 d . . . . .
O1 O 0.4009(9) 0.4826(3) 0.3978(4) 0.0665(13) Uani 1 1 d . . . . .
N1 N 0.4155(7) 0.2824(4) 0.3686(4) 0.0486(10) Uani 1 1 d . . . . .
O3 O 0.3448(10) 0.3396(5) -0.0235(5) 0.0754(15) Uani 1 1 d . . . . .
H3 H 0.266449 0.389936 -0.030839 0.113 Uiso 1 1 calc R U . . .
C4 C 0.4088(7) 0.2365(4) 0.4797(5) 0.0439(10) Uani 1 1 d . . . . .
C9 C 0.3948(10) 0.3050(4) 0.5768(5) 0.0530(12) Uani 1 1 d . . . . .
H9 H 0.389399 0.386046 0.569365 0.064 Uiso 1 1 calc R U . . .
C008 C 0.4052(9) 0.3977(5) 0.3369(5) 0.0511(12) Uani 1 1 d . . . . .
C3 C 0.4175(11) 0.2070(5) 0.2688(5) 0.0570(15) Uani 1 1 d . . . . .
H3A H 0.305353 0.163356 0.262244 0.068 Uiso 1 1 calc R U . . .
H3B H 0.518186 0.152528 0.271783 0.068 Uiso 1 1 calc R U . . .
C2 C 0.4391(8) 0.2929(5) 0.1698(5) 0.0533(13) Uani 1 1 d . . . . .
H2 H 0.563428 0.289715 0.140515 0.064 Uiso 1 1 calc R U . . .
C7 C 0.4011(8) 0.1346(5) 0.6957(5) 0.0501(11) Uani 1 1 d . . . . .
C6 C 0.4148(9) 0.0650(5) 0.6023(6) 0.0557(13) Uani 1 1 d . . . . .
H6 H 0.419292 -0.015897 0.610531 0.067 Uiso 1 1 calc R U . . .
C8 C 0.3889(10) 0.2557(5) 0.6845(5) 0.0582(14) Uani 1 1 d . . . . .
H8 H 0.376734 0.302827 0.748954 0.070 Uiso 1 1 calc R U . . .
C5 C 0.4222(10) 0.1149(5) 0.4942(5) 0.0550(14) Uani 1 1 d . . . . .
H5 H 0.436223 0.067109 0.430376 0.066 Uiso 1 1 calc R U . . .
C1 C 0.3071(10) 0.2715(6) 0.0733(5) 0.0589(14) Uani 1 1 d . . . . .
H1A H 0.310800 0.189414 0.052259 0.071 Uiso 1 1 calc R U . . .
H1B H 0.185480 0.289038 0.099715 0.071 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0829(10) 0.0628(8) 0.0497(7) 0.0073(6) 0.0002(8) 0.0020(8)
O2 0.090(3) 0.048(2) 0.049(2) 0.0006(17) 0.003(2) -0.007(2)
O1 0.102(4) 0.0390(18) 0.058(2) -0.0059(18) 0.013(3) 0.002(3)
N1 0.058(2) 0.042(2) 0.047(2) -0.0042(18) 0.002(2) -0.003(2)
O3 0.103(4) 0.070(3) 0.054(2) 0.008(2) 0.002(3) 0.017(3)
C4 0.043(2) 0.042(2) 0.046(3) -0.006(2) 0.002(2) -0.003(2)
C9 0.068(3) 0.037(2) 0.054(3) -0.006(2) 0.004(3) -0.002(3)
C008 0.057(3) 0.045(2) 0.051(3) -0.001(2) 0.000(3) 0.000(2)
C3 0.083(4) 0.046(3) 0.042(3) -0.006(2) 0.000(3) -0.004(3)
C2 0.061(3) 0.048(3) 0.050(3) 0.000(2) 0.003(3) -0.003(2)
C7 0.050(2) 0.051(2) 0.049(3) 0.000(2) 0.002(3) 0.000(2)
C6 0.066(3) 0.042(2) 0.059(3) -0.001(2) 0.003(3) -0.001(3)
C8 0.075(3) 0.053(3) 0.046(3) -0.012(2) 0.001(3) 0.000(3)
C5 0.073(4) 0.044(3) 0.048(3) -0.006(2) 0.000(3) -0.001(3)
C1 0.073(3) 0.056(3) 0.048(3) -0.003(2) 0.003(3) -0.005(3)

_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 C7 1.750(6) . ?
O2 C008 1.343(7) . ?
O2 C2 1.460(7) . ?
O1 C008 1.203(7) . ?
N1 C4 1.401(7) . ?
N1 C008 1.370(7) . ?
N1 C3 1.449(7) . ?
O3 H3 0.8200 . ?
O3 C1 1.400(8) . ?
C4 C9 1.382(8) . ?
C4 C5 1.402(8) . ?
C9 H9 0.9300 . ?
C9 C8 1.379(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.524(8) . ?
C2 H2 0.9800 . ?
C2 C1 1.510(9) . ?
C7 C6 1.353(9) . ?
C7 C8 1.393(8) . ?
C6 H6 0.9300 . ?
C6 C5 1.386(9) . ?
C8 H8 0.9300 . ?
C5 H5 0.9300 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

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
C008 O2 C2 110.5(5) . . ?
C4 N1 C3 121.6(4) . . ?
C008 N1 C4 127.4(5) . . ?
C008 N1 C3 110.8(5) . . ?
C1 O3 H3 109.5 . . ?
N1 C4 C5 118.7(5) . . ?
C9 C4 N1 123.4(5) . . ?
C9 C4 C5 117.9(5) . . ?
C4 C9 H9 119.4 . . ?
C8 C9 C4 121.3(5) . . ?
C8 C9 H9 119.4 . . ?
O2 C008 N1 110.1(5) . . ?
O1 C008 O2 121.8(6) . . ?
O1 C008 N1 128.1(6) . . ?
N1 C3 H3A 111.1 . . ?
N1 C3 H3B 111.1 . . ?
N1 C3 C2 103.3(4) . . ?
H3A C3 H3B 109.1 . . ?
C2 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
O2 C2 C3 103.7(5) . . ?
O2 C2 H2 109.8 . . ?
O2 C2 C1 110.4(5) . . ?
C3 C2 H2 109.8 . . ?
C1 C2 C3 113.3(5) . . ?
C1 C2 H2 109.8 . . ?
C6 C7 Cl1 119.0(5) . . ?
C6 C7 C8 120.8(6) . . ?
C8 C7 Cl1 120.2(5) . . ?
C7 C6 H6 120.1 . . ?
C7 C6 C5 119.7(5) . . ?
C5 C6 H6 120.1 . . ?
C9 C8 C7 119.3(5) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.9(5) . . ?
C6 C5 H5 119.5 . . ?
O3 C1 C2 112.6(6) . . ?
O3 C1 H1A 109.1 . . ?
O3 C1 H1B 109.1 . . ?
C2 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C7 C6 C5 -179.5(5) . . . . ?
Cl1 C7 C8 C9 180.0(5) . . . . ?
O2 C2 C1 O3 72.8(7) . . . . ?
N1 C4 C9 C8 -179.9(6) . . . . ?
N1 C4 C5 C6 -179.5(6) . . . . ?
N1 C3 C2 O2 -12.4(7) . . . . ?
N1 C3 C2 C1 -132.1(6) . . . . ?
C4 N1 C008 O2 -176.3(6) . . . . ?
C4 N1 C008 O1 5.7(11) . . . . ?
C4 N1 C3 C2 -176.0(5) . . . . ?
C4 C9 C8 C7 1.4(11) . . . . ?
C9 C4 C5 C6 2.4(10) . . . . ?
C008 O2 C2 C3 12.3(7) . . . . ?
C008 O2 C2 C1 133.9(6) . . . . ?
C008 N1 C4 C9 -1.8(10) . . . . ?
C008 N1 C4 C5 -179.9(6) . . . . ?
C008 N1 C3 C2 9.2(7) . . . . ?
C3 N1 C4 C9 -175.7(6) . . . . ?
C3 N1 C4 C5 6.3(9) . . . . ?
C3 N1 C008 O2 -1.9(8) . . . . ?
C3 N1 C008 O1 -180.0(8) . . . . ?
C3 C2 C1 O3 -171.4(6) . . . . ?
C2 O2 C008 O1 171.3(6) . . . . ?
C2 O2 C008 N1 -7.0(8) . . . . ?
C7 C6 C5 C4 -2.4(10) . . . . ?
C6 C7 C8 C9 -1.4(11) . . . . ?
C8 C7 C6 C5 1.9(10) . . . . ?
C5 C4 C9 C8 -1.9(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
