# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_3
_database_code_depnum_ccdc_archive 'CCDC 2053205'
loop_
_audit_author_name
_audit_author_address
'Subhankar Saha'
;IISER Kolkata
India
;
_audit_update_record             
;
2020-12-30 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;
_audit_creation_date             2020-12-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 Cl3 O2'
_chemical_formula_sum            'C13 H7 Cl3 O2'
_chemical_formula_weight         301.54
_chemical_absolute_configuration ?
_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 0.0033 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'
O O 0.0106 0.0060 '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                   3.927(4)
_cell_length_b                   11.665(12)
_cell_length_c                   27.84(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1275(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2833
_cell_measurement_temperature    293(2)
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      33.8
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.920
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1780
_diffrn_reflns_av_unetI/netI     0.1077
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            10764
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         3.409
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.638
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1939
_reflns_number_total             2250
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 
;
 Flack x determined using 565 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0623
_refine_ls_restrained_S_all      1.083
_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)+(0.0387P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1294
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C002(H002), C004(H004), C009(H009), C012(H012), C013(H013), C014(H014),
 C015(H015)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.3944(4) 0.86593(14) 0.18638(6) 0.0591(5) Uani 1 1 d . . . . .
Cl2 Cl 0.3097(4) 1.16086(13) 0.03779(7) 0.0585(5) Uani 1 1 d . . . . .
Cl3 Cl 1.0811(5) 0.20816(15) 0.21342(7) 0.0688(6) Uani 1 1 d . . . . .
O1 O 0.7676(10) 0.7208(3) 0.11918(15) 0.0488(11) Uani 1 1 d . . . . .
C002 C 0.3799(15) 1.0063(4) 0.1091(2) 0.0421(13) Uani 1 1 d . . . . .
H002 H 0.265115 1.058594 0.128381 0.050 Uiso 1 1 calc R . . . .
O2 O 0.4827(13) 0.6144(4) 0.06482(18) 0.0657(14) Uani 1 1 d . . . . .
C004 C 0.8102(15) 0.3147(5) 0.1368(2) 0.0516(16) Uani 1 1 d . . . . .
H004 H 0.771197 0.241341 0.124974 0.062 Uiso 1 1 calc R . . . .
C005 C 0.4483(14) 1.0314(5) 0.0619(2) 0.0406(13) Uani 1 1 d . . . . .
C006 C 0.7773(13) 0.5204(5) 0.1289(2) 0.0390(13) Uani 1 1 d . . . . .
C007 C 0.6564(14) 0.6194(5) 0.0998(2) 0.0417(13) Uani 1 1 d . . . . .
C008 C 0.9621(15) 0.3292(5) 0.1806(2) 0.0476(14) Uani 1 1 d . . . . .
C009 C 0.7240(13) 0.8498(5) 0.0504(2) 0.0452(15) Uani 1 1 d . . . . .
H009 H 0.840014 0.797883 0.031090 0.054 Uiso 1 1 calc R . . . .
C010 C 0.4859(14) 0.9002(5) 0.1277(2) 0.0383(12) Uani 1 1 d . . . . .
C011 C 0.6537(13) 0.8235(4) 0.0979(2) 0.0387(13) Uani 1 1 d . . . . .
C012 C 1.0269(15) 0.4365(5) 0.1997(2) 0.0495(15) Uani 1 1 d . . . . .
H012 H 1.129247 0.444319 0.229620 0.059 Uiso 1 1 calc R . . . .
C013 C 0.7142(15) 0.4103(5) 0.1099(2) 0.0471(14) Uani 1 1 d . . . . .
H013 H 0.610591 0.401619 0.080111 0.057 Uiso 1 1 calc R . . . .
C014 C 0.6193(13) 0.9544(5) 0.0322(2) 0.0424(13) Uani 1 1 d . . . . .
H014 H 0.662713 0.973165 0.000283 0.051 Uiso 1 1 calc R . . . .
C015 C 0.9348(15) 0.5331(5) 0.1728(2) 0.0465(14) Uani 1 1 d . . . . .
H015 H 0.980097 0.606101 0.184605 0.056 Uiso 1 1 calc R . . . .


_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 C010 1.719(6) . ?
Cl2 C005 1.741(6) . ?
Cl3 C008 1.745(6) . ?
O1 C007 1.372(6) . ?
O1 C011 1.409(6) . ?
C002 C005 1.371(8) . ?
C002 C010 1.405(7) . ?
O2 C007 1.190(7) . ?
C004 C008 1.368(9) . ?
C004 C013 1.394(8) . ?
C005 C014 1.394(8) . ?
C006 C007 1.489(7) . ?
C006 C013 1.411(8) . ?
C006 C015 1.377(8) . ?
C008 C012 1.383(8) . ?
C009 C011 1.385(8) . ?
C009 C014 1.384(8) . ?
C010 C011 1.386(8) . ?
C012 C015 1.400(9) . ?

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
C007 O1 C011 117.9(4) . . ?
C005 C002 C010 118.9(5) . . ?
C008 C004 C013 119.8(6) . . ?
C002 C005 Cl2 119.6(4) . . ?
C002 C005 C014 121.7(6) . . ?
C014 C005 Cl2 118.7(5) . . ?
C013 C006 C007 116.5(5) . . ?
C015 C006 C007 122.8(5) . . ?
C015 C006 C013 120.7(5) . . ?
O1 C007 C006 110.7(5) . . ?
O2 C007 O1 123.1(5) . . ?
O2 C007 C006 126.2(5) . . ?
C004 C008 Cl3 118.9(5) . . ?
C004 C008 C012 122.3(6) . . ?
C012 C008 Cl3 118.8(5) . . ?
C011 C009 C014 119.1(5) . . ?
C002 C010 Cl1 119.6(4) . . ?
C011 C010 Cl1 121.2(4) . . ?
C011 C010 C002 119.2(6) . . ?
C009 C011 O1 121.7(5) . . ?
C009 C011 C010 121.5(5) . . ?
C010 C011 O1 116.6(5) . . ?
C008 C012 C015 118.4(6) . . ?
C004 C013 C006 118.6(6) . . ?
C009 C014 C005 119.5(6) . . ?
C006 C015 C012 120.2(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
