# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_RSR
_database_code_depnum_ccdc_archive 'CCDC 1922202'
loop_
_audit_author_name
_audit_author_address
'Rajesh G. Gonnade'
;National Chemical Laboratory, Pune
India
;
_audit_update_record             
;
2019-06-11 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        RSR-4e
_chemical_name_common            ?
_chemical_melting_point          471-472
_chemical_formula_moiety         'C12 H6 Cl2 N2 O2'
_chemical_formula_sum            'C12 H6 Cl2 N2 O2'
_chemical_formula_weight         281.09

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'
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'
Cl Cl 0.1484 0.1585 '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 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   10.4975(2)
_cell_length_b                   14.8593(4)
_cell_length_c                   7.2597(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.3700(10)
_cell_angle_gamma                90
_cell_volume                     1110.18(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7567
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      32.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.577
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            24444
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.407
_diffrn_reflns_theta_max         32.584
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4005
_reflns_number_gt                3315
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0218P)²+0.8753P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4005
_refine_ls_number_parameters     181
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.69439(3) 0.44375(3) 0.90420(5) 0.01679(8) Uani 1 1 d . . . . .
Cl2 Cl 0.35230(3) 0.68569(2) 0.54872(5) 0.01759(8) Uani 1 1 d . . . . .
O1 O 0.05482(10) 0.44833(8) 0.73554(17) 0.0201(2) Uani 1 1 d . . . . .
O2 O 0.32966(10) 0.23434(7) 0.56926(16) 0.0187(2) Uani 1 1 d . . . . .
N1 N 0.21949(11) 0.36015(8) 0.65117(16) 0.0117(2) Uani 1 1 d . U . . .
C1 C 0.09817(13) 0.37677(10) 0.7022(2) 0.0138(3) Uani 1 1 d . U . . .
C2 C 0.23794(13) 0.26742(10) 0.62054(19) 0.0135(3) Uani 1 1 d . U . . .
C3 C 0.1279(7) 0.2217(5) 0.6576(11) 0.0142(13) Uani 0.6 1 d D U P A 1
N2 N 0.0474(4) 0.2893(4) 0.7013(8) 0.0099(9) Uani 0.6 1 d D U P A 1
N2' N 0.1178(8) 0.2292(6) 0.6660(13) 0.0104(16) Uani 0.4 1 d D U P A 2
C3' C 0.0322(8) 0.2915(8) 0.7131(14) 0.0121(17) Uani 0.4 1 d D U P A 2
C4 C 0.06704(14) 0.14226(10) 0.6720(2) 0.0157(3) Uani 1 1 d . . . . .
H4 H 0.1000 0.0846 0.6498 0.019 Uiso 1 1 calc R U . A 1
C5 C -0.05271(14) 0.15883(11) 0.7250(2) 0.0173(3) Uani 1 1 d . . . . .
H5 H -0.1135 0.1141 0.7440 0.021 Uiso 1 1 calc R U . . .
C6 C -0.06782(13) 0.25097(10) 0.7451(2) 0.0152(3) Uani 1 1 d . . . . .
H6 H -0.1388 0.2816 0.7801 0.018 Uiso 1 1 calc R U . A 1
C7 C 0.31957(12) 0.42609(9) 0.66689(18) 0.0110(2) Uani 1 1 d . . . . .
C8 C 0.44374(13) 0.40373(10) 0.76391(19) 0.0122(2) Uani 1 1 d . . . . .
H8 H 0.4630 0.3449 0.8129 0.015 Uiso 1 1 calc R U . . .
C9 C 0.53819(12) 0.47021(10) 0.78650(19) 0.0127(3) Uani 1 1 d . . . . .
C10 C 0.51221(13) 0.55739(10) 0.72274(19) 0.0134(2) Uani 1 1 d . . . . .
H10 H 0.5775 0.6025 0.7438 0.016 Uiso 1 1 calc R U . . .
C11 C 0.38724(13) 0.57634(9) 0.62703(19) 0.0122(2) Uani 1 1 d . . . . .
C12 C 0.29011(12) 0.51184(9) 0.59312(19) 0.0114(2) Uani 1 1 d . . . . .
H12 H 0.2063 0.5256 0.5220 0.014 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 1.7381(13) . ?
Cl2 C11 1.7366(14) . ?
O1 C1 1.1999(18) . ?
O2 C2 1.2035(18) . ?
N1 C2 1.4151(18) . ?
N1 C1 1.4162(18) . ?
N1 C7 1.4247(17) . ?
C1 N2 1.405(6) . ?
C1 C3' 1.453(11) . ?
C2 C3 1.411(8) . ?
C2 N2' 1.479(9) . ?
C3 C4 1.357(8) . ?
C3 N2 1.388(8) . ?
N2 C6 1.428(5) . ?
N2' C3' 1.379(11) . ?
N2' C4 1.401(9) . ?
C3' C6 1.271(10) . ?
C4 C5 1.407(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.3930(19) . ?
C7 C8 1.3941(18) . ?
C8 C9 1.3862(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(2) . ?
C10 C11 1.3870(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.3856(19) . ?
C12 H12 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
C2 N1 C1 111.65(11) . . ?
C2 N1 C7 124.10(11) . . ?
C1 N1 C7 123.09(12) . . ?
O1 C1 N2 131.5(2) . . ?
O1 C1 N1 127.14(13) . . ?
N2 C1 N1 101.4(2) . . ?
O1 C1 C3' 123.9(4) . . ?
N1 C1 C3' 109.0(4) . . ?
O2 C2 C3 126.7(3) . . ?
O2 C2 N1 126.08(13) . . ?
C3 C2 N1 107.2(3) . . ?
O2 C2 N2' 133.0(3) . . ?
N1 C2 N2' 100.9(3) . . ?
C4 C3 N2 107.1(6) . . ?
C4 C3 C2 148.1(6) . . ?
N2 C3 C2 104.7(5) . . ?
C3 N2 C1 115.0(5) . . ?
C3 N2 C6 110.1(5) . . ?
C1 N2 C6 134.8(4) . . ?
C3' N2' C4 110.0(8) . . ?
C3' N2' C2 115.0(7) . . ?
C4 N2' C2 135.0(6) . . ?
C6 C3' N2' 109.2(9) . . ?
C6 C3' C1 147.4(8) . . ?
N2' C3' C1 103.4(7) . . ?
C3 C4 C5 109.2(3) . . ?
N2' C4 C5 102.3(4) . . ?
C3 C4 H4 125.4 . . ?
C5 C4 H4 125.4 . . ?
C6 C5 C4 109.14(13) . . ?
C6 C5 H5 125.4 . . ?
C4 C5 H5 125.4 . . ?
C3' C6 C5 109.4(5) . . ?
C5 C6 N2 104.5(3) . . ?
C5 C6 H6 127.8 . . ?
N2 C6 H6 127.8 . . ?
C12 C7 C8 121.80(12) . . ?
C12 C7 N1 119.60(11) . . ?
C8 C7 N1 118.54(12) . . ?
C9 C8 C7 117.75(13) . . ?
C9 C8 H8 121.1 . . ?
C7 C8 H8 121.1 . . ?
C10 C9 C8 122.55(12) . . ?
C10 C9 Cl1 118.72(11) . . ?
C8 C9 Cl1 118.71(11) . . ?
C9 C10 C11 117.51(13) . . ?
C9 C10 H10 121.2 . . ?
C11 C10 H10 121.2 . . ?
C12 C11 C10 122.61(13) . . ?
C12 C11 Cl2 119.24(10) . . ?
C10 C11 Cl2 118.15(11) . . ?
C11 C12 C7 117.68(12) . . ?
C11 C12 H12 121.2 . . ?
C7 C12 H12 121.2 . . ?

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
C2 N1 C1 O1 -179.42(14) . . . . ?
C7 N1 C1 O1 12.4(2) . . . . ?
C2 N1 C1 N2 0.5(3) . . . . ?
C7 N1 C1 N2 -167.7(2) . . . . ?
C2 N1 C1 C3' 1.9(4) . . . . ?
C7 N1 C1 C3' -166.2(4) . . . . ?
C1 N1 C2 O2 177.11(14) . . . . ?
C7 N1 C2 O2 -14.9(2) . . . . ?
C1 N1 C2 C3 -1.7(4) . . . . ?
C7 N1 C2 C3 166.3(3) . . . . ?
C1 N1 C2 N2' -2.3(4) . . . . ?
C7 N1 C2 N2' 165.7(4) . . . . ?
O2 C2 C3 C4 4.8(14) . . . . ?
N1 C2 C3 C4 -176.4(10) . . . . ?
O2 C2 C3 N2 -176.6(3) . . . . ?
N1 C2 C3 N2 2.2(6) . . . . ?
C4 C3 N2 C1 177.1(4) . . . . ?
C2 C3 N2 C1 -2.1(7) . . . . ?
C4 C3 N2 C6 0.2(7) . . . . ?
C2 C3 N2 C6 -179.1(4) . . . . ?
O1 C1 N2 C3 -179.1(4) . . . . ?
N1 C1 N2 C3 1.0(5) . . . . ?
O1 C1 N2 C6 -3.1(7) . . . . ?
N1 C1 N2 C6 177.0(5) . . . . ?
O2 C2 N2' C3' -177.3(5) . . . . ?
N1 C2 N2' C3' 2.0(8) . . . . ?
O2 C2 N2' C4 2.1(13) . . . . ?
N1 C2 N2' C4 -178.6(8) . . . . ?
C4 N2' C3' C6 -0.9(10) . . . . ?
C2 N2' C3' C6 178.7(6) . . . . ?
C4 N2' C3' C1 179.5(6) . . . . ?
C2 N2' C3' C1 -0.9(10) . . . . ?
O1 C1 C3' C6 1.4(17) . . . . ?
N1 C1 C3' C6 -179.8(13) . . . . ?
O1 C1 C3' N2' -179.3(5) . . . . ?
N1 C1 C3' N2' -0.6(8) . . . . ?
N2 C3 C4 C5 0.0(6) . . . . ?
C2 C3 C4 C5 178.6(10) . . . . ?
C3' N2' C4 C5 0.1(8) . . . . ?
C2 N2' C4 C5 -179.4(8) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
N2' C4 C5 C6 0.7(4) . . . . ?
N2' C3' C6 C5 1.3(9) . . . . ?
C1 C3' C6 C5 -179.4(13) . . . . ?
C4 C5 C6 C3' -1.3(5) . . . . ?
C4 C5 C6 N2 0.2(3) . . . . ?
C3 N2 C6 C5 -0.2(5) . . . . ?
C1 N2 C6 C5 -176.4(5) . . . . ?
C2 N1 C7 C12 143.68(13) . . . . ?
C1 N1 C7 C12 -49.65(18) . . . . ?
C2 N1 C7 C8 -39.17(18) . . . . ?
C1 N1 C7 C8 127.50(14) . . . . ?
C12 C7 C8 C9 0.5(2) . . . . ?
N1 C7 C8 C9 -176.62(12) . . . . ?
C7 C8 C9 C10 2.4(2) . . . . ?
C7 C8 C9 Cl1 -179.16(10) . . . . ?
C8 C9 C10 C11 -2.4(2) . . . . ?
Cl1 C9 C10 C11 179.14(10) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
C9 C10 C11 Cl2 179.17(10) . . . . ?
C10 C11 C12 C7 3.1(2) . . . . ?
Cl2 C11 C12 C7 -176.53(10) . . . . ?
C8 C7 C12 C11 -3.1(2) . . . . ?
N1 C7 C12 C11 173.99(12) . . . . ?

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
C10 H10 O2 0.95 2.47 3.3108(18) 147.3 2_656
C6 H6 Cl2 0.95 2.97 3.4413(14) 111.7 3_566
C5 H5 O1 0.95 2.54 3.141(2) 121.7 2_546
C5 H5 Cl1 0.95 2.99 3.5153(15) 116.4 4_465

_refine_diff_density_max         0.462
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.074

