# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_RK4C
_database_code_depnum_ccdc_archive 'CCDC 2056338'
loop_
_audit_author_name
_audit_author_address
'E Suresh'
;CSIR CSMCRI
India
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ORGANIC
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 Cl2 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         337.19

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.5085(11)
_cell_length_b                   6.9929(5)
_cell_length_c                   14.8594(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.310(2)
_cell_angle_gamma                90
_cell_volume                     1507.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9944
_cell_measurement_theta_min      2.7416
_cell_measurement_theta_max      30.4925
_cell_measurement_temperature    127.(2)

_exptl_crystal_description       PLATES
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.439
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.064
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696

_exptl_absorpt_coefficient_mu    0.439
_exptl_absorpt_correction_type   'MULTI SCAN'
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_min  0.8310
_exptl_absorpt_correction_T_max  0.9720

_exptl_special_details           
;
;

_diffrn_ambient_temperature      127.(2)

_diffrn_source                   'MICRO FOCUS TUBE'
_diffrn_source_type              ?

_diffrn_radiation_type           Mok\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 quest'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            26805
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         30.56
_diffrn_reflns_theta_full        30.56
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
;

_reflns_number_total             4599
_reflns_number_gt                3844
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_gt          0.1718
_refine_ls_wR_factor_ref         0.1830
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_number_reflns         4599
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0848P)²+2.7269P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.255
_refine_diff_density_min         -0.825
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.87188(5) 0.59312(9) 1.11615(4) 0.03362(18) Uani d . . . 1 . .
Cl Cl2 0.76510(5) 0.57601(11) 0.31720(4) 0.0389(2) Uani d . . . 1 . .
O O1 0.53456(12) 0.4752(3) 0.75970(12) 0.0284(4) Uani d . . . 1 . .
O O2 0.49471(18) 0.1864(4) 0.89886(17) 0.0557(7) Uani d . . . 1 . .
N N1 0.67768(14) 0.5942(2) 0.60328(12) 0.0206(4) Uani d . . . 1 . .
N N2 0.81939(14) 0.5554(3) 0.66075(13) 0.0227(4) Uani d . . . 1 . .
C C1 0.72290(16) 0.5300(3) 0.89184(15) 0.0222(4) Uani d . . . 1 . .
C C2 0.74927(17) 0.5351(3) 0.98158(15) 0.0249(4) Uani d . . . 1 . .
C C3 0.83882(17) 0.5853(3) 1.00358(15) 0.0239(4) Uani d . . . 1 . .
C C4 0.90295(18) 0.6264(3) 0.93765(16) 0.0264(5) Uani d . . . 1 . .
C C5 0.87534(16) 0.6233(3) 0.84804(15) 0.0234(4) Uani d . . . 1 . .
C C6 0.78517(16) 0.5784(3) 0.82399(14) 0.0200(4) Uani d . . . 1 . .
C C7 0.75667(16) 0.5800(3) 0.72898(14) 0.0199(4) Uani d . . . 1 . .
C C8 0.66883(16) 0.6073(3) 0.69561(14) 0.0203(4) Uani d . . . 1 . .
C C9 0.77038(16) 0.5637(3) 0.58515(15) 0.0217(4) Uani d . . . 1 . .
C C10 0.79919(19) 0.5523(3) 0.49460(16) 0.0265(5) Uani d . . . 1 . .
C C11 0.73370(19) 0.5733(3) 0.42926(15) 0.0268(5) Uani d . . . 1 . .
C C12 0.63926(19) 0.5975(3) 0.44911(15) 0.0265(5) Uani d . . . 1 . .
C C13 0.61259(17) 0.6080(3) 0.53650(15) 0.0234(4) Uani d . . . 1 . .
C C14 0.58018(16) 0.6512(3) 0.73997(15) 0.0231(4) Uani d . . . 1 . .
C C15 0.4593(2) 0.4902(4) 0.8194(2) 0.0392(6) Uani d . . . 1 . .
H H15A 0.407654 0.55988 0.790367 0.047 Uiso calc U . R 1 . .
H H15B 0.477785 0.560073 0.874528 0.047 Uiso calc U . R 1 . .
C C16 0.4301(2) 0.2861(5) 0.8426(2) 0.0429(7) Uani d . . . 1 . .
H H16A 0.369807 0.290396 0.873339 0.052 Uiso calc U . R 1 . .
H H16B 0.421773 0.213219 0.78599 0.052 Uiso calc U . R 1 . .
H H1 0.662(2) 0.485(5) 0.874(2) 0.031(8) Uiso d . . . 1 . .
H H2 0.701(2) 0.499(5) 1.025(2) 0.038(9) Uiso d . . . 1 . .
H H2C 0.5057(18) 0.024(4) 0.9047(18) 0.016(6) Uiso d . . . 1 . .
H H4 0.966(2) 0.656(5) 0.951(2) 0.031(8) Uiso d . . . 1 . .
H H5 0.917(2) 0.666(5) 0.802(2) 0.029(8) Uiso d . . . 1 . .
H H10 0.859(2) 0.532(5) 0.482(2) 0.028(8) Uiso d . . . 1 . .
H H12 0.593(2) 0.597(4) 0.407(2) 0.027(8) Uiso d . . . 1 . .
H H13 0.548(2) 0.631(5) 0.552(2) 0.028(8) Uiso d . . . 1 . .
H H14A 0.5943(18) 0.723(4) 0.7953(18) 0.015(6) Uiso d . . . 1 . .
H H14B 0.543(2) 0.728(4) 0.703(2) 0.023(7) Uiso d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C3 . 1.738(2) ?
Cl2 C11 . 1.729(2) ?
O1 C15 . 1.415(3) ?
O1 C14 . 1.428(3) ?
O2 C16 . 1.433(4) ?
O2 H2C . 1.15(3) ?
N1 C13 . 1.370(3) ?
N1 C8 . 1.382(3) ?
N1 C9 . 1.389(3) ?
N2 C9 . 1.328(3) ?
N2 C7 . 1.377(3) ?
C1 C2 . 1.386(3) ?
C1 C6 . 1.399(3) ?
C1 H1 . 0.97(3) ?
C2 C3 . 1.383(4) ?
C2 H2 . 0.99(4) ?
C3 C4 . 1.385(3) ?
C4 C5 . 1.388(3) ?
C4 H4 . 0.96(3) ?
C5 C6 . 1.390(3) ?
C5 H5 . 0.96(3) ?
C6 C7 . 1.469(3) ?
C7 C8 . 1.378(3) ?
C8 C14 . 1.481(3) ?
C9 C10 . 1.413(3) ?
C10 C11 . 1.363(4) ?
C10 H10 . 0.90(3) ?
C11 C12 . 1.413(4) ?
C12 C13 . 1.359(3) ?
C12 H12 . 0.92(3) ?
C13 H13 . 0.98(3) ?
C14 H14A . 0.99(3) ?
C14 H14B . 0.94(3) ?
C15 C16 . 1.529(4) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C15 O1 C14 . . 115.17(19) ?
C16 O2 H2C . . 127.9(14) ?
C13 N1 C8 . . 130.3(2) ?
C13 N1 C9 . . 122.32(19) ?
C8 N1 C9 . . 107.34(19) ?
C9 N2 C7 . . 105.34(19) ?
C2 C1 C6 . . 120.7(2) ?
C2 C1 H1 . . 121.2(19) ?
C6 C1 H1 . . 118.0(19) ?
C3 C2 C1 . . 119.2(2) ?
C3 C2 H2 . . 125.(2) ?
C1 C2 H2 . . 116.(2) ?
C2 C3 C4 . . 121.3(2) ?
C2 C3 Cl1 . . 119.29(18) ?
C4 C3 Cl1 . . 119.42(19) ?
C3 C4 C5 . . 118.9(2) ?
C3 C4 H4 . . 123.0(19) ?
C5 C4 H4 . . 118.1(19) ?
C4 C5 C6 . . 121.1(2) ?
C4 C5 H5 . . 119.6(19) ?
C6 C5 H5 . . 119.0(19) ?
C5 C6 C1 . . 118.7(2) ?
C5 C6 C7 . . 120.33(19) ?
C1 C6 C7 . . 121.0(2) ?
N2 C7 C8 . . 111.47(19) ?
N2 C7 C6 . . 121.5(2) ?
C8 C7 C6 . . 126.99(19) ?
C7 C8 N1 . . 104.91(19) ?
C7 C8 C14 . . 132.2(2) ?
N1 C8 C14 . . 122.8(2) ?
N2 C9 N1 . . 110.93(19) ?
N2 C9 C10 . . 130.0(2) ?
N1 C9 C10 . . 119.0(2) ?
C11 C10 C9 . . 117.6(2) ?
C11 C10 H10 . . 123.(2) ?
C9 C10 H10 . . 120.(2) ?
C10 C11 C12 . . 122.5(2) ?
C10 C11 Cl2 . . 120.1(2) ?
C12 C11 Cl2 . . 117.42(19) ?
C13 C12 C11 . . 119.2(2) ?
C13 C12 H12 . . 116.(2) ?
C11 C12 H12 . . 124.(2) ?
C12 C13 N1 . . 119.3(2) ?
C12 C13 H13 . . 121.2(19) ?
N1 C13 H13 . . 119.4(19) ?
O1 C14 C8 . . 108.52(18) ?
O1 C14 H14A . . 111.4(16) ?
C8 C14 H14A . . 107.5(15) ?
O1 C14 H14B . . 110.4(19) ?
C8 C14 H14B . . 110.7(18) ?
H14A C14 H14B . . 108.(2) ?
O1 C15 C16 . . 106.7(2) ?
O1 C15 H15A . . 110.4 ?
C16 C15 H15A . . 110.4 ?
O1 C15 H15B . . 110.4 ?
C16 C15 H15B . . 110.4 ?
H15A C15 H15B . . 108.6 ?
O2 C16 C15 . . 113.9(3) ?
O2 C16 H16A . . 108.8 ?
C15 C16 H16A . . 108.8 ?
O2 C16 H16B . . 108.8 ?
C15 C16 H16B . . 108.8 ?
H16A C16 H16B . . 107.7 ?

