# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_chz_pa
_database_code_depnum_ccdc_archive 'CCDC 1982306'
loop_
_audit_author_name
_audit_author_address
'PARAG ROY'
;BIRLA INSTITUTE OF TECHNOLOGY
India
;
_audit_update_record             
;
2020-02-06 deposited with the CCDC.	2020-06-08 downloaded from the CCDC.
;
_audit_creation_date             2020-02-06
_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        CHZ_PA
_chemical_formula_moiety         'C7 H4 Cl N O2, C6 H5 N O2'
_chemical_formula_sum            'C13 H9 Cl N2 O4'
_chemical_formula_weight         292.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H9 Cl N2 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5903(4)
_cell_length_b                   9.0809(6)
_cell_length_c                   9.7444(5)
_cell_angle_alpha                99.238(5)
_cell_angle_beta                 107.382(5)
_cell_angle_gamma                101.179(5)
_cell_volume                     611.46(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2639
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.2310
_cell_measurement_theta_min      4.4350
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.908
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.590
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_preparation       'LIQUID ASSISTED GRINDING WITH ACN'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0092
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4909
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.445
_diffrn_reflns_theta_min         3.617
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4324
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  79.00   1.00   12.57    --   10.22  57.00 -90.00   91
  2  ω    -59.00  35.00   1.00   12.57    --   10.22 -57.00 120.00   94
  3  ω    -67.00  15.00   1.00   12.57    --  -10.38 -57.00 -30.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0519477000
_diffrn_orient_matrix_UB_12      -0.0028748000
_diffrn_orient_matrix_UB_13      -0.0745888000
_diffrn_orient_matrix_UB_21      -0.0203688000
_diffrn_orient_matrix_UB_22      0.0710818000
_diffrn_orient_matrix_UB_23      0.0228066000
_diffrn_orient_matrix_UB_31      0.0845666000
_diffrn_orient_matrix_UB_32      0.0405398000
_diffrn_orient_matrix_UB_33      -0.0083108000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2464
_reflns_number_total             2843
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2843
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.048
_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)+(0.0570P)²+0.1051P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1043
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H6), C10(H7), C3(H5), C5(H3), C12(H8), C6(H2), C4(H4), C13(H9)
;
_atom_sites_solution_hydrogens   mixed
_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 0.32465(6) 0.64048(5) 0.04706(4) 0.05591(15) Uani 1 1 d . . . . .
O4 O 0.79452(15) 0.69664(11) 0.65445(10) 0.0423(2) Uani 1 1 d . . . . .
O1 O 0.89292(17) 0.14000(13) 0.46730(11) 0.0527(3) Uani 1 1 d . . . . .
O2 O 0.68212(19) 0.20154(14) 0.28791(12) 0.0589(3) Uani 1 1 d . . . . .
O3 O 0.94596(17) 0.52131(14) 0.74096(12) 0.0549(3) Uani 1 1 d . . . . .
N1 N 0.91542(17) -0.09720(13) 0.27046(13) 0.0367(3) Uani 1 1 d . . . . .
N2 N 0.76790(17) 0.48477(13) 0.49258(13) 0.0387(3) Uani 1 1 d . . . . .
H6 H 0.781225 0.397118 0.454626 0.046 Uiso 1 1 calc R . . . .
C2 C 0.81827(18) 0.00336(15) 0.22133(14) 0.0336(3) Uani 1 1 d . . . . .
C9 C 0.66256(18) 0.57119(14) 0.41434(14) 0.0327(3) Uani 1 1 d . . . . .
C1 C 0.7958(2) 0.12599(15) 0.33633(15) 0.0376(3) Uani 1 1 d . . . . .
C10 C 0.55433(19) 0.54734(15) 0.26759(15) 0.0379(3) Uani 1 1 d . . . . .
H7 H 0.541541 0.459410 0.197876 0.045 Uiso 1 1 calc R . . . .
C7 C 0.8472(2) 0.55773(16) 0.63758(16) 0.0400(3) Uani 1 1 d . . . . .
C3 C 0.7438(2) -0.01060(17) 0.07178(15) 0.0407(3) Uani 1 1 d . . . . .
H5 H 0.676227 0.058052 0.035172 0.049 Uiso 1 1 calc R . . . .
C8 C 0.68044(19) 0.70319(15) 0.51692(14) 0.0359(3) Uani 1 1 d . . . . .
C11 C 0.4654(2) 0.66231(16) 0.22978(15) 0.0387(3) Uani 1 1 d . . . . .
C5 C 0.8700(2) -0.22881(17) 0.02997(16) 0.0452(3) Uani 1 1 d . . . . .
H3 H 0.888838 -0.307131 -0.033955 0.054 Uiso 1 1 calc R . . . .
C12 C 0.4827(2) 0.79360(17) 0.33180(17) 0.0458(3) Uani 1 1 d . . . . .
H8 H 0.420383 0.867564 0.301543 0.055 Uiso 1 1 calc R . . . .
C6 C 0.9416(2) -0.21250(17) 0.17990(16) 0.0427(3) Uani 1 1 d . . . . .
H2 H 1.007887 -0.280881 0.218734 0.051 Uiso 1 1 calc R . . . .
C4 C 0.7698(2) -0.12773(18) -0.02458(16) 0.0475(4) Uani 1 1 d . . . . .
H4 H 0.719530 -0.137858 -0.126136 0.057 Uiso 1 1 calc R . . . .
C13 C 0.5927(2) 0.81575(17) 0.47954(17) 0.0471(4) Uani 1 1 d . . . . .
H9 H 0.605899 0.903428 0.549710 0.057 Uiso 1 1 calc R . . . .
H1 H 0.967(3) -0.089(2) 0.365(2) 0.067(6) Uiso 1 1 d . . . . .


_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 C11 1.7374(14) . ?
O4 C7 1.3953(17) . ?
O4 C8 1.3790(16) . ?
O1 C1 1.2402(17) . ?
O2 C1 1.2360(17) . ?
O3 C7 1.1991(18) . ?
N1 C2 1.3407(17) . ?
N1 C6 1.3428(18) . ?
N2 C9 1.3812(17) . ?
N2 C7 1.3544(18) . ?
C2 C1 1.5207(18) . ?
C2 C3 1.3711(18) . ?
C9 C10 1.3770(18) . ?
C9 C8 1.3876(17) . ?
C10 C11 1.3893(19) . ?
C3 C4 1.387(2) . ?
C8 C13 1.364(2) . ?
C11 C12 1.381(2) . ?
C5 C6 1.370(2) . ?
C5 C4 1.374(2) . ?
C12 C13 1.391(2) . ?

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
C8 O4 C7 107.22(10) . . ?
C2 N1 C6 123.06(12) . . ?
C7 N2 C9 110.33(11) . . ?
N1 C2 C1 117.44(11) . . ?
N1 C2 C3 118.70(12) . . ?
C3 C2 C1 123.86(12) . . ?
N2 C9 C8 105.92(11) . . ?
C10 C9 N2 132.85(12) . . ?
C10 C9 C8 121.23(12) . . ?
O1 C1 C2 117.07(12) . . ?
O2 C1 O1 127.16(13) . . ?
O2 C1 C2 115.77(12) . . ?
C9 C10 C11 116.09(12) . . ?
O3 C7 O4 121.41(14) . . ?
O3 C7 N2 131.13(14) . . ?
N2 C7 O4 107.46(12) . . ?
C2 C3 C4 119.59(13) . . ?
O4 C8 C9 109.07(11) . . ?
C13 C8 O4 128.37(12) . . ?
C13 C8 C9 122.56(13) . . ?
C10 C11 Cl1 119.01(11) . . ?
C12 C11 Cl1 118.24(11) . . ?
C12 C11 C10 122.76(13) . . ?
C6 C5 C4 119.02(13) . . ?
C11 C12 C13 120.34(13) . . ?
N1 C6 C5 119.60(13) . . ?
C5 C4 C3 120.02(13) . . ?
C8 C13 C12 117.03(13) . . ?


_olex2_submission_original_sample_id CHZ_PA
_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 1.260
_oxdiff_exptl_absorpt_empirical_full_min 0.796
