# Electronic Supplementary Material (ESI) for ChemComm.
# 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_ussrnb1_134_1_rt_cu_auto
_database_code_depnum_ccdc_archive 'CCDC 2300817'
loop_
_audit_author_name
_audit_author_address
'PUNEET SOOD'
;IIT Mandi
India
;
_audit_update_record             
;
2023-10-12 deposited with the CCDC.	2024-05-01 downloaded from the CCDC.
;
_audit_creation_date             2023-10-10
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 Cl N O'
_chemical_formula_sum            'C18 H14 Cl N O'
_chemical_formula_weight         295.75
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C72  H56  Cl4  N4  O4  '
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      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                   7.8569(6)
_cell_length_b                   16.8285(13)
_cell_length_c                   11.2120(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.254(7)
_cell_angle_gamma                90
_cell_volume                     1436.81(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1763
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.3850
_cell_measurement_theta_min      4.8610
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.323
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.416
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             616
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 3 7 0.2318
0 -3 -7 0.1286
-1 -10 2 0.1702
1 10 -2 0.1702
5 0 0 0.0765
-5 0 0 0.0765
2 5 -6 0.1446
-2 -6 6 0.1648
0 -10 -2 0.1397
3 -9 -1 0.1194
-5 2 2 0.1131
3 -5 4 0.1266
3 2 4 0.1462
-4 -5 4 0.1234
-5 -2 -1 0.0670
-5 1 -1 0.0626

_exptl_crystal_size_max          0.635
_exptl_crystal_size_mid          0.387
_exptl_crystal_size_min          0.143
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.3127 3.1653 6.8432 0.3236 0.9156 -0.2388
0.3758 -2.5685 -6.9648 -0.3277 -0.9270 0.1823
-1.1098 -10.1779 2.4616 0.0876 0.2458 0.9654
1.1098 10.1779 -2.4616 -0.0876 -0.2458 -0.9654
4.9822 -0.0276 -0.2474 0.9565 -0.2293 -0.1804
-4.9822 0.0276 0.2474 -0.9565 0.2293 0.1804
1.8775 4.8669 -6.4217 -0.1095 -0.8367 -0.5365
-1.8544 -6.2787 5.8308 0.0975 0.7454 0.6594
-0.1708 -10.4156 -2.0506 -0.0099 -0.3669 0.9302
2.8156 -9.0922 -1.2540 0.6033 -0.3698 0.7066
-4.9685 2.2497 2.3677 -0.8528 0.5221 -0.0090
2.7068 -5.0109 4.0760 0.8580 0.3556 0.3708
3.4596 2.0820 3.7879 0.8828 0.3663 -0.2942
-4.1499 -5.2952 3.7374 -0.4965 0.5814 0.6446
-4.5928 -2.3794 -1.0413 -0.9264 0.0241 0.3757
-4.6343 0.5438 -1.2925 -0.9932 0.0256 0.1138

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4102
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.974
_diffrn_reflns_theta_min         4.844
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -101.00 -51.00   1.00    1.00    --  -24.78 -57.00-180.00   50
  2  ω    -63.00  42.00   1.00    1.00    --  -24.78  77.00  60.00  105
  3  ω    -15.00  37.00   1.00    1.00    --   24.78  77.00 150.00   52
  4  ω   -125.00 -48.00   1.00    1.50    --  -69.25 178.00-120.00   77
  5  ω    114.00 155.00   1.00    1.50    --   69.25 111.00-180.00   41
  6  ω    109.00 154.00   1.00    1.50    --   69.25 111.00 -30.00   45
  7  ω    106.00 153.00   1.00    1.50    --   69.25 111.00  60.00   47
  8  ω    -21.00 159.00   1.00    1.50    --   69.25  12.00 -60.00  180
  9  ω    122.00 165.00   1.00    2.44    --  113.72  43.00-180.00   43
 10  ω     83.00 118.00   1.00    2.44    --  113.72  43.00-180.00   35
 11  ω     26.00 158.00   1.00    2.44    --  113.72 -21.00 -30.00  132
 12  ω     25.00 106.00   1.00    2.44    --  113.72 -89.00-120.00   81
 13  ω     29.00 108.00   1.00    2.44    --  113.72-104.00  90.00   79
 14  ω     48.00 103.00   1.00    2.44    --  113.72-104.00-150.00   55
 15  ω     34.00 143.00   1.00    2.44    --  113.72 -65.00  60.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1950274000
_diffrn_orient_matrix_UB_12      -0.0146465000
_diffrn_orient_matrix_UB_13      0.0629698000
_diffrn_orient_matrix_UB_21      -0.0396565000
_diffrn_orient_matrix_UB_22      0.0108804000
_diffrn_orient_matrix_UB_23      0.1269498000
_diffrn_orient_matrix_UB_31      -0.0364565000
_diffrn_orient_matrix_UB_32      -0.0896821000
_diffrn_orient_matrix_UB_33      0.0049254000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2042
_reflns_number_total             2554
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0009(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2554
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.026
_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)+(0.0908P)²+0.1112P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1540
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C17(H17), C11(H11), C5(H5), C13(H13), C1(H1), C12(H12), C4(H4),
 C3(H3), C2(H2)
2.c X=CH2 refined with riding coordinates:
 C18(H18A,H18B)
;
_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 0.79299(10) 0.44598(5) 0.18891(6) 0.0786(3) Uani 1 1 d . . . . .
O1 O 0.6307(2) 0.31301(9) 0.62320(13) 0.0537(4) Uani 1 1 d . . . . .
N1 N 0.6565(2) 0.30349(10) 0.42784(15) 0.0452(4) Uani 1 1 d . . . . .
C15 C 0.7048(2) 0.43165(12) 0.52899(18) 0.0432(5) Uani 1 1 d . . . . .
C16 C 0.6611(2) 0.34642(12) 0.53360(17) 0.0424(5) Uani 1 1 d . . . . .
C8 C 0.6961(3) 0.33449(14) 0.32503(18) 0.0495(5) Uani 1 1 d . . . . .
H8 H 0.690371 0.302218 0.256831 0.059 Uiso 1 1 calc R U . . .
C14 C 0.7036(3) 0.48211(13) 0.62986(19) 0.0480(5) Uani 1 1 d . . . . .
C10 C 0.7498(3) 0.46271(13) 0.42395(19) 0.0480(5) Uani 1 1 d . . . . .
C6 C 0.4079(3) 0.20728(12) 0.39349(19) 0.0463(5) Uani 1 1 d . . . . .
C7 C 0.6044(3) 0.21888(12) 0.4259(2) 0.0490(5) Uani 1 1 d . . . . .
H7A H 0.654058 0.195775 0.506187 0.059 Uiso 1 1 calc R U . . .
H7B H 0.653178 0.190736 0.366455 0.059 Uiso 1 1 calc R U . . .
C9 C 0.7428(3) 0.41068(15) 0.32168(19) 0.0525(5) Uani 1 1 d . . . . .
C17 C 0.6462(3) 0.45695(13) 0.7419(2) 0.0544(5) Uani 1 1 d . . . . .
H17 H 0.551978 0.422029 0.731839 0.065 Uiso 1 1 calc R U . . .
C11 C 0.7986(3) 0.54305(14) 0.4213(2) 0.0590(6) Uani 1 1 d . . . . .
H11 H 0.830116 0.563562 0.352795 0.071 Uiso 1 1 calc R U . . .
C5 C 0.3062(3) 0.23280(15) 0.2809(2) 0.0581(6) Uani 1 1 d . . . . .
H5 H 0.359667 0.257979 0.225864 0.070 Uiso 1 1 calc R U . . .
C13 C 0.7512(3) 0.56123(13) 0.6222(2) 0.0601(6) Uani 1 1 d . . . . .
H13 H 0.750564 0.595128 0.687563 0.072 Uiso 1 1 calc R U . . .
C1 C 0.3253(4) 0.16915(16) 0.4723(2) 0.0637(6) Uani 1 1 d . . . . .
H1 H 0.391127 0.151389 0.548284 0.076 Uiso 1 1 calc R U . . .
C12 C 0.7992(3) 0.59097(15) 0.5206(2) 0.0659(7) Uani 1 1 d . . . . .
H12 H 0.832395 0.643948 0.519288 0.079 Uiso 1 1 calc R U . . .
C4 C 0.1271(3) 0.22144(17) 0.2492(3) 0.0675(7) Uani 1 1 d . . . . .
H4 H 0.060632 0.239704 0.173812 0.081 Uiso 1 1 calc R U . . .
C3 C 0.0466(3) 0.18344(16) 0.3282(3) 0.0705(7) Uani 1 1 d . . . . .
H3 H -0.074305 0.175576 0.306513 0.085 Uiso 1 1 calc R U . . .
C2 C 0.1451(4) 0.15692(18) 0.4399(3) 0.0784(8) Uani 1 1 d . . . . .
H2 H 0.091067 0.130770 0.493772 0.094 Uiso 1 1 calc R U . . .
C18 C 0.7204(5) 0.48108(18) 0.8519(3) 0.0845(9) Uani 1 1 d . . . . .
H18A H 0.814871 0.516010 0.864664 0.101 Uiso 1 1 calc R U . . .
H18B H 0.679234 0.463500 0.918348 0.101 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 C9 1.736(2) . ?
O1 C16 1.225(2) . ?
N1 C16 1.381(3) . ?
N1 C8 1.369(3) . ?
N1 C7 1.480(3) . ?
C15 C16 1.479(3) . ?
C15 C14 1.416(3) . ?
C15 C10 1.411(3) . ?
C8 C9 1.337(3) . ?
C14 C17 1.496(3) . ?
C14 C13 1.392(3) . ?
C10 C9 1.433(3) . ?
C10 C11 1.408(3) . ?
C6 C7 1.509(3) . ?
C6 C5 1.386(3) . ?
C6 C1 1.377(3) . ?
C17 C18 1.293(4) . ?
C11 C12 1.373(4) . ?
C5 C4 1.377(3) . ?
C13 C12 1.379(4) . ?
C1 C2 1.387(4) . ?
C4 C3 1.367(4) . ?
C3 C2 1.375(4) . ?

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
C16 N1 C7 117.68(17) . . ?
C8 N1 C16 124.06(18) . . ?
C8 N1 C7 118.26(17) . . ?
C14 C15 C16 120.42(19) . . ?
C10 C15 C16 119.77(19) . . ?
C10 C15 C14 119.80(19) . . ?
O1 C16 N1 119.65(18) . . ?
O1 C16 C15 124.59(19) . . ?
N1 C16 C15 115.76(17) . . ?
C9 C8 N1 120.7(2) . . ?
C15 C14 C17 124.29(19) . . ?
C13 C14 C15 118.0(2) . . ?
C13 C14 C17 117.6(2) . . ?
C15 C10 C9 118.27(19) . . ?
C11 C10 C15 119.9(2) . . ?
C11 C10 C9 121.8(2) . . ?
C5 C6 C7 120.4(2) . . ?
C1 C6 C7 121.4(2) . . ?
C1 C6 C5 118.2(2) . . ?
N1 C7 C6 112.99(17) . . ?
C8 C9 Cl1 118.32(18) . . ?
C8 C9 C10 121.3(2) . . ?
C10 C9 Cl1 120.34(18) . . ?
C18 C17 C14 123.6(3) . . ?
C12 C11 C10 119.6(2) . . ?
C4 C5 C6 121.0(2) . . ?
C12 C13 C14 122.1(2) . . ?
C6 C1 C2 120.8(2) . . ?
C11 C12 C13 120.6(2) . . ?
C3 C4 C5 120.3(3) . . ?
C4 C3 C2 119.7(2) . . ?
C3 C2 C1 120.0(3) . . ?

_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 1.541
_oxdiff_exptl_absorpt_empirical_full_min 0.700
