# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_c
_database_code_depnum_ccdc_archive 'CCDC 1953617'
loop_
_audit_author_name
_audit_author_address
'Rupali Mittal'
;University of Delhi
India
;
_audit_update_record             
;
2019-09-14 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;
_audit_creation_date             2019-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        5-(3-chlorobenzyl)-1H-tetrazole
_chemical_formula_moiety         'C8 H7 Cl N4'
_chemical_formula_sum            'C8 H7 Cl N4'
_chemical_formula_weight         194.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H7 Cl N4'
_chemical_oxdiff_usercomment     28-08-2019
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'

_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/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                   4.8058(5)
_cell_length_b                   26.6823(19)
_cell_length_c                   7.1899(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.575(10)
_cell_angle_gamma                90
_cell_volume                     883.65(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2632
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4860
_cell_measurement_theta_min      3.7240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.386
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54089
_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
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate: Hexane (1:1)'
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11098
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.327
_diffrn_ambient_temperature      296
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9853
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  87.00   1.00    2.50    --   18.84  57.00   0.00   87
  2  ω      6.00  87.00   1.00    2.50    --   18.84  57.00 -90.00   81
  3  ω    -25.00  59.00   1.00    2.50    --   18.84 -99.00 -60.00   84
  4  ω    -25.00  59.00   1.00    2.50    --   18.84 -99.00-150.00   84
  5  ω    -48.00  35.00   1.00    2.50    --   18.84 -57.00   0.00   83
  6  ω    -25.00  59.00   1.00    2.50    --   18.84 -99.00 120.00   84
  7  ω     -6.00  82.00   1.00    2.50    --   18.84  77.00 150.00   88
  8  ω    -82.00  -1.00   1.00    2.50    --  -15.17 -57.00  30.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0782383000
_diffrn_orient_matrix_UB_12      0.0220179000
_diffrn_orient_matrix_UB_13      -0.0381814000
_diffrn_orient_matrix_UB_21      0.1269001000
_diffrn_orient_matrix_UB_22      0.0145769000
_diffrn_orient_matrix_UB_23      0.0386433000
_diffrn_orient_matrix_UB_31      0.0383747000
_diffrn_orient_matrix_UB_32      -0.0031717000
_diffrn_orient_matrix_UB_33      -0.0874456000
_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'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1379
_reflns_number_total             1617
_reflns_odcompleteness_completeness 99.67
_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         0.250
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1617
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0718
_refine_ls_restrained_S_all      1.206
_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)+(0.0319P)²+1.0298P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1463
_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:
 C2(H2), C6(H6), C5(H5), C4(H4A)
;
_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 0.1121(3) 0.45591(5) 0.18894(19) 0.0862(5) Uani 1 1 d . . . . .
N4 N 0.9201(6) 0.23754(11) 0.4383(4) 0.0428(7) Uani 1 1 d . . . . .
N1 N 0.6912(6) 0.25972(11) 0.6379(4) 0.0451(7) Uani 1 1 d . . . . .
N3 N 0.8146(7) 0.19534(11) 0.4932(4) 0.0503(8) Uani 1 1 d . . . . .
N2 N 0.6776(7) 0.20895(11) 0.6140(5) 0.0510(8) Uani 1 1 d . . . . .
C8 C 0.8449(7) 0.27680(12) 0.5253(5) 0.0364(8) Uani 1 1 d . . . . .
C1 C 0.7195(7) 0.36872(12) 0.5300(5) 0.0417(8) Uani 1 1 d . . . . .
C2 C 0.5350(8) 0.39186(13) 0.3700(5) 0.0479(9) Uani 1 1 d . . . . .
H2 H 0.538831 0.382940 0.245671 0.057 Uiso 1 1 calc R . . . .
C6 C 0.7087(8) 0.38282(14) 0.7142(5) 0.0478(9) Uani 1 1 d . . . . .
H6 H 0.831013 0.367581 0.823558 0.057 Uiso 1 1 calc R . . . .
C7 C 0.9315(8) 0.32943(13) 0.5046(6) 0.0495(9) Uani 1 1 d . . . . .
H7A H 0.958737 0.333429 0.376833 0.059 Uiso 1 1 calc R . . . .
H7B H 1.117342 0.335534 0.599316 0.059 Uiso 1 1 calc R . . . .
C5 C 0.5172(9) 0.41929(15) 0.7345(6) 0.0557(10) Uani 1 1 d . . . . .
H5 H 0.511491 0.428606 0.858045 0.067 Uiso 1 1 calc R . . . .
C3 C 0.3462(8) 0.42803(14) 0.3951(6) 0.0510(9) Uani 1 1 d . . . . .
C4 C 0.3328(8) 0.44232(14) 0.5737(6) 0.0536(10) Uani 1 1 d . . . . .
H4A H 0.203133 0.466926 0.587543 0.064 Uiso 1 1 calc R . . . .
H4 H 1.010(9) 0.2366(15) 0.353(6) 0.063(13) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0806(9) 0.0860(9) 0.0748(8) 0.0235(7) -0.0057(6) 0.0054(7)
N4 0.0445(17) 0.0504(18) 0.0426(17) 0.0021(14) 0.0273(15) -0.0001(14)
N1 0.0479(17) 0.0530(18) 0.0456(17) 0.0001(14) 0.0314(14) -0.0024(14)
N3 0.061(2) 0.0488(18) 0.0520(19) 0.0010(14) 0.0340(17) -0.0024(15)
N2 0.060(2) 0.0526(19) 0.0525(19) 0.0032(15) 0.0352(16) -0.0047(16)
C8 0.0322(17) 0.048(2) 0.0323(17) -0.0029(14) 0.0143(14) 0.0010(14)
C1 0.0399(18) 0.0382(19) 0.050(2) -0.0025(16) 0.0184(16) -0.0078(15)
C2 0.055(2) 0.045(2) 0.046(2) -0.0028(16) 0.0191(18) -0.0137(18)
C6 0.046(2) 0.055(2) 0.043(2) 0.0003(17) 0.0123(17) 0.0031(17)
C7 0.049(2) 0.051(2) 0.058(2) -0.0031(18) 0.0303(19) -0.0045(18)
C5 0.062(2) 0.060(2) 0.049(2) -0.0100(19) 0.022(2) 0.000(2)
C3 0.049(2) 0.047(2) 0.052(2) 0.0056(17) 0.0061(18) -0.0082(18)
C4 0.047(2) 0.048(2) 0.066(3) -0.0013(19) 0.017(2) 0.0046(18)

_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 C3 1.750(4) . ?
N4 N3 1.340(4) . ?
N4 C8 1.323(4) . ?
N4 H4 0.84(4) . ?
N1 N2 1.365(4) . ?
N1 C8 1.323(4) . ?
N3 N2 1.283(4) . ?
C8 C7 1.484(5) . ?
C1 C2 1.382(5) . ?
C1 C6 1.392(5) . ?
C1 C7 1.509(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.376(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C4 1.384(5) . ?
C3 C4 1.359(5) . ?
C4 H4A 0.9300 . ?

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
N3 N4 H4 120(3) . . ?
C8 N4 N3 110.4(3) . . ?
C8 N4 H4 129(3) . . ?
C8 N1 N2 106.2(3) . . ?
N2 N3 N4 105.8(3) . . ?
N3 N2 N1 110.5(3) . . ?
N4 C8 C7 125.4(3) . . ?
N1 C8 N4 107.0(3) . . ?
N1 C8 C7 127.5(3) . . ?
C2 C1 C6 118.9(3) . . ?
C2 C1 C7 120.3(3) . . ?
C6 C1 C7 120.8(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.0(4) . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C1 115.3(3) . . ?
C8 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
C1 C7 H7A 108.5 . . ?
C1 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C6 C5 H5 119.5 . . ?
C6 C5 C4 120.9(4) . . ?
C4 C5 H5 119.5 . . ?
C2 C3 Cl1 118.5(3) . . ?
C4 C3 Cl1 119.3(3) . . ?
C4 C3 C2 122.2(4) . . ?
C5 C4 H4A 120.9 . . ?
C3 C4 C5 118.3(4) . . ?
C3 C4 H4A 120.9 . . ?

_shelx_res_file                  
;
TITL c_a.res in P2(1)/n
    c.res
    created by SHELXL-2017/1 at 15:30:36 on 12-Sep-2019
REM Old TITL c_a.res in P2(1)/n
REM SHELXT solution in P2(1)/n
REM R1 0.194, Rweak 0.066, Alpha 0.049, Orientation as input
REM Formula found by SHELXT: C9 Cl N3
CELL 0.71073 4.8058 26.6823 7.1899 90 106.575 90
ZERR 4 0.0005 0.0019 0.0007 0 0.01 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H Cl N
UNIT 32 28 4 16

L.S. 10
PLAN  20
TEMP 22.85
BOND $H
LIST 6
fmap 2
acta
SHEL 100 0.83
REM <olex2.extras>
REM <HklSrc "%.\\C.hkl">
REM </olex2.extras>

WGHT    0.031900    1.029800
FVAR       0.89706
CL1   3    0.112147    0.455908    0.188937    11.00000    0.08062    0.08598 =
         0.07479    0.02350   -0.00575    0.00537
N4    4    0.920145    0.237538    0.438261    11.00000    0.04452    0.05041 =
         0.04258    0.00213    0.02726   -0.00008
N1    4    0.691201    0.259720    0.637914    11.00000    0.04790    0.05295 =
         0.04562    0.00014    0.03137   -0.00240
N3    4    0.814610    0.195343    0.493193    11.00000    0.06119    0.04883 =
         0.05199    0.00098    0.03397   -0.00240
N2    4    0.677588    0.208948    0.613967    11.00000    0.05972    0.05260 =
         0.05248    0.00322    0.03524   -0.00474
C8    1    0.844881    0.276798    0.525347    11.00000    0.03219    0.04790 =
         0.03228   -0.00292    0.01430    0.00104
C1    1    0.719481    0.368723    0.530034    11.00000    0.03991    0.03823 =
         0.05037   -0.00251    0.01838   -0.00783
C2    1    0.534976    0.391863    0.369950    11.00000    0.05514    0.04509 =
         0.04628   -0.00276    0.01910   -0.01365
AFIX  43
H2    2    0.538831    0.382940    0.245671    11.00000   -1.20000
AFIX   0
C6    1    0.708736    0.382816    0.714232    11.00000    0.04554    0.05500 =
         0.04263    0.00029    0.01225    0.00306
AFIX  43
H6    2    0.831013    0.367581    0.823558    11.00000   -1.20000
AFIX   0
C7    1    0.931505    0.329434    0.504595    11.00000    0.04878    0.05121 =
         0.05798   -0.00309    0.03034   -0.00452
AFIX  23
H7A   2    0.958737    0.333429    0.376833    11.00000   -1.20000
H7B   2    1.117342    0.335534    0.599316    11.00000   -1.20000
AFIX   0
C5    1    0.517165    0.419294    0.734534    11.00000    0.06212    0.05996 =
         0.04874   -0.01001    0.02160   -0.00003
AFIX  43
H5    2    0.511491    0.428606    0.858045    11.00000   -1.20000
AFIX   0
C3    1    0.346200    0.428029    0.395061    11.00000    0.04861    0.04750 =
         0.05181    0.00560    0.00613   -0.00817
C4    1    0.332820    0.442315    0.573717    11.00000    0.04674    0.04839 =
         0.06624   -0.00131    0.01702    0.00458
AFIX  43
H4A   2    0.203133    0.466926    0.587543    11.00000   -1.20000
AFIX   0
H4    2    1.010323    0.236567    0.353344    11.00000    0.06273
HKLF 4




REM  c_a.res in P2(1)/n
REM R1 =  0.0718 for    1379 Fo > 4sig(Fo)  and  0.0832 for all    1617 data
REM    122 parameters refined using      0 restraints

END

WGHT      0.0319      1.0297

REM Highest difference peak  0.250,  deepest hole -0.241,  1-sigma level  0.050
Q1    1   0.1282  0.5040  0.2105  11.00000  0.05    0.25
Q2    1   0.1213  0.4157  0.1308  11.00000  0.05    0.25
Q3    1   0.9300  0.3011  0.5343  11.00000  0.05    0.20
Q4    1   0.8856  0.1610  0.5006  11.00000  0.05    0.18
Q5    1   0.9297  0.2702  0.4776  11.00000  0.05    0.16
Q6    1   0.8298  0.2340  0.1522  11.00000  0.05    0.16
Q7    1   0.6859  0.3463  0.6767  11.00000  0.05    0.16
Q8    1   0.2748  0.4825 -0.0335  11.00000  0.05    0.15
Q9    1   0.7385  0.2976  0.6778  11.00000  0.05    0.15
Q10   1   0.8307  0.2339  0.5269  11.00000  0.05    0.15
Q11   1   0.2943  0.4642  0.1608  11.00000  0.05    0.15
Q12   1   0.3290  0.3639  0.0628  11.00000  0.05    0.15
Q13   1   0.7134  0.1687  0.6084  11.00000  0.05    0.15
Q14   1   0.1548  0.4876  0.0847  11.00000  0.05    0.14
Q15   1  -0.0354  0.4947  0.2520  11.00000  0.05    0.14
Q16   1   0.5752  0.3567  0.2333  11.00000  0.05    0.14
Q17   1   0.5450  0.4560  0.7129  11.00000  0.05    0.14
Q18   1   0.2728  0.4173  0.9884  11.00000  0.05    0.13
Q19   1   1.0229  0.3302  0.4541  11.00000  0.05    0.13
Q20   1  -0.0496  0.3924  0.1455  11.00000  0.05    0.13
;
_shelx_res_checksum              9975
_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 1.610
_oxdiff_exptl_absorpt_empirical_full_min 0.591
