# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_20220627_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2182535'
loop_
_audit_author_name
_audit_author_address
lmz-et
;centeral south university
China
;
_audit_update_record             
;
2022-06-28 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_audit_creation_date             2022-06-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '4(C10 H9 Cl N2 O)'
_chemical_formula_sum            'C40 H36 Cl4 N8 O4'
_chemical_formula_weight         834.57
_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 0.0148 0.0070 '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 0.3294 0.5404 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.3980(3)
_cell_length_b                   10.9637(4)
_cell_length_c                   11.9743(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.8516(14)
_cell_angle_gamma                90.00
_cell_volume                     950.52(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5246
_cell_measurement_temperature    156(2)
_cell_measurement_theta_max      56.954
_cell_measurement_theta_min      5.646
_exptl_absorpt_coefficient_mu    2.139
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1542 before and 0.0616 after correction.
The Ratio of minimum to maximum transmission is 0.7499.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BAR
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6184
_diffrn_reflns_theta_full        56.99
_diffrn_reflns_theta_max         56.99
_diffrn_reflns_theta_min         5.65
_diffrn_ambient_temperature      156.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1788
_reflns_number_total             1920
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1920
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0575P)²+0.3643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1058
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C1(H1), C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.10320(5) 0.13790(3) 0.03476(3) 0.02862(17) Uani 1 d . . .
O1 O 0.15190(17) 0.23202(10) -0.18586(9) 0.0302(3) Uani 1 d . . .
N2 N 0.18484(17) 0.36365(11) 0.08933(11) 0.0214(3) Uani 1 d . . .
N1 N 0.23793(16) 0.42611(11) -0.12919(10) 0.0179(3) Uani 1 d . . .
C5 C 0.26079(18) 0.51542(13) -0.04396(12) 0.0177(3) Uani 1 d . . .
C4 C 0.3096(2) 0.63621(13) -0.06303(13) 0.0221(3) Uani 1 d . . .
H4 H 0.3285 0.6604 -0.1360 0.027 Uiso 1 calc . . R
C8 C 0.1813(2) 0.30980(13) -0.11136(12) 0.0212(3) Uani 1 d . . .
C1 C 0.2555(2) 0.56843(14) 0.15241(12) 0.0234(3) Uani 1 d . . .
H1 H 0.2376 0.5451 0.2258 0.028 Uiso 1 calc . . R
C7 C 0.1622(2) 0.28670(13) 0.00805(12) 0.0201(3) Uani 1 d . . .
C10 C 0.0935(2) 0.49354(16) -0.32540(12) 0.0271(4) Uani 1 d . . .
H10A H 0.1217 0.5164 -0.3991 0.041 Uiso 1 calc . . GR
H10B H 0.0409 0.5638 -0.2927 0.041 Uiso 1 calc . . GR
H10C H 0.0042 0.4263 -0.3364 0.041 Uiso 1 calc . . GR
C3 C 0.3299(2) 0.71969(14) 0.02509(14) 0.0257(3) Uani 1 d . . .
H3 H 0.3629 0.8013 0.0117 0.031 Uiso 1 calc . . R
C9 C 0.2693(2) 0.45333(14) -0.24480(12) 0.0211(3) Uani 1 d . . .
H9A H 0.3182 0.3796 -0.2761 0.025 Uiso 1 calc . . R
H9B H 0.3631 0.5186 -0.2396 0.025 Uiso 1 calc . . R
C6 C 0.23332(18) 0.48189(13) 0.06476(12) 0.0188(3) Uani 1 d . . .
C2 C 0.3031(2) 0.68714(15) 0.13351(14) 0.0261(3) Uani 1 d . . .
H2 H 0.3175 0.7458 0.1931 0.031 Uiso 1 calc . . R

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 0.0372(3) 0.0205(2) 0.0285(3) 0.00634(13) 0.00753(17) -0.00028(14)
O1 0.0475(7) 0.0210(6) 0.0237(6) -0.0045(4) 0.0111(5) -0.0001(5)
N2 0.0197(6) 0.0255(7) 0.0192(6) 0.0032(5) 0.0046(5) 0.0012(5)
N1 0.0204(6) 0.0191(6) 0.0147(6) 0.0002(4) 0.0046(4) 0.0022(5)
C5 0.0149(6) 0.0211(7) 0.0163(7) 0.0010(5) 0.0017(5) 0.0034(5)
C4 0.0227(7) 0.0239(8) 0.0197(7) 0.0017(5) 0.0043(6) -0.0003(5)
C8 0.0236(7) 0.0207(7) 0.0195(7) 0.0013(6) 0.0052(5) 0.0047(6)
C1 0.0215(7) 0.0318(8) 0.0173(7) -0.0028(6) 0.0053(5) -0.0014(6)
C7 0.0210(7) 0.0199(7) 0.0196(7) 0.0042(5) 0.0047(5) 0.0032(5)
C10 0.0272(8) 0.0343(9) 0.0187(7) 0.0047(6) 0.0021(6) 0.0003(6)
C3 0.0251(7) 0.0232(8) 0.0278(8) -0.0004(6) 0.0035(6) -0.0024(6)
C9 0.0232(7) 0.0259(8) 0.0150(7) 0.0010(6) 0.0060(5) 0.0010(6)
C6 0.0159(6) 0.0220(7) 0.0185(7) 0.0005(5) 0.0032(5) 0.0010(5)
C2 0.0249(7) 0.0294(8) 0.0238(8) -0.0088(6) 0.0043(6) -0.0029(6)

_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 1.7354(15) . ?
O1 C8 1.2209(19) . ?
N2 C7 1.273(2) . ?
N2 C6 1.3926(19) . ?
N1 C5 1.3994(18) . ?
N1 C8 1.3727(19) . ?
N1 C9 1.4802(17) . ?
C5 C4 1.404(2) . ?
C5 C6 1.4070(19) . ?
C4 H4 0.9500 . ?
C4 C3 1.382(2) . ?
C8 C7 1.487(2) . ?
C1 H1 0.9500 . ?
C1 C6 1.399(2) . ?
C1 C2 1.379(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 C9 1.517(2) . ?
C3 H3 0.9500 . ?
C3 C2 1.399(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C2 H2 0.9500 . ?

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
C7 N2 C6 117.04(13) . . ?
C5 N1 C9 121.49(12) . . ?
C8 N1 C5 122.11(12) . . ?
C8 N1 C9 116.38(12) . . ?
N1 C5 C4 122.56(13) . . ?
N1 C5 C6 118.24(13) . . ?
C4 C5 C6 119.20(13) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 C5 119.48(14) . . ?
C3 C4 H4 120.3 . . ?
O1 C8 N1 123.32(13) . . ?
O1 C8 C7 123.09(14) . . ?
N1 C8 C7 113.58(12) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C2 C1 C6 120.75(13) . . ?
N2 C7 Cl1 118.73(11) . . ?
N2 C7 C8 126.78(14) . . ?
C8 C7 Cl1 114.48(11) . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
C4 C3 H3 119.1 . . ?
C4 C3 C2 121.72(15) . . ?
C2 C3 H3 119.1 . . ?
N1 C9 C10 112.03(12) . . ?
N1 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N2 C6 C5 122.08(13) . . ?
N2 C6 C1 117.93(13) . . ?
C1 C6 C5 119.99(13) . . ?
C1 C2 C3 118.85(14) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?

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
O1 C8 C7 Cl1 2.37(19) . . . . ?
O1 C8 C7 N2 -177.73(15) . . . . ?
N1 C5 C4 C3 -179.98(13) . . . . ?
N1 C5 C6 N2 0.08(19) . . . . ?
N1 C5 C6 C1 179.77(12) . . . . ?
N1 C8 C7 Cl1 -176.58(10) . . . . ?
N1 C8 C7 N2 3.3(2) . . . . ?
C5 N1 C8 O1 176.41(13) . . . . ?
C5 N1 C8 C7 -4.64(19) . . . . ?
C5 N1 C9 C10 -91.75(16) . . . . ?
C5 C4 C3 C2 0.0(2) . . . . ?
C4 C5 C6 N2 -179.98(12) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
C4 C3 C2 C1 0.1(2) . . . . ?
C8 N1 C5 C4 -176.68(12) . . . . ?
C8 N1 C5 C6 3.26(19) . . . . ?
C8 N1 C9 C10 86.75(15) . . . . ?
C7 N2 C6 C5 -1.5(2) . . . . ?
C7 N2 C6 C1 178.84(13) . . . . ?
C9 N1 C5 C4 1.7(2) . . . . ?
C9 N1 C5 C6 -178.33(11) . . . . ?
C9 N1 C8 O1 -2.1(2) . . . . ?
C9 N1 C8 C7 176.87(11) . . . . ?
C6 N2 C7 Cl1 179.58(10) . . . . ?
C6 N2 C7 C8 -0.3(2) . . . . ?
C6 C5 C4 C3 0.1(2) . . . . ?
C6 C1 C2 C3 -0.3(2) . . . . ?
C2 C1 C6 N2 -179.89(13) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
