# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_SNZ2BZU
_database_code_depnum_ccdc_archive 'CCDC 2251452'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir'
;University of Sargodha, Pakistan
Pakistan
;
_audit_update_record             
;
2023-03-24 deposited with the CCDC.	2023-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
N-(2-methylphenyl)-5-phenyl-1,3,4-oxadiazol-2-amine
;
_chemical_formula_moiety         'C15 H13 N3 O'
_chemical_formula_sum            'C15 H13 N3 O'
_chemical_formula_iupac          'C15 H13 N3 O'
_chemical_formula_weight         251.28

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'

_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                   8.5156(16)
_cell_length_b                   7.2615(15)
_cell_length_c                   20.971(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.424(9)
_cell_angle_gamma                90
_cell_volume                     1294.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2374
_cell_measurement_theta_min      3.176
_cell_measurement_theta_max      27.949
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.6418
_exptl_absorpt_correction_T_max  0.7456
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.975
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.50
_diffrn_reflns_number            11008
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.176
_diffrn_reflns_theta_max         27.949
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total             3064
_reflns_number_gt                2374
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1600
_refine_ls_wR_factor_gt          0.1470
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_number_reflns         3064
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0816P)²+0.2366P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_extinction_method     ?
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression ?
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2  (Sheldrick, 2019)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2009)
;

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
O1 O 0.15188(12) 0.69733(14) 0.02928(4) 0.0380(3) Uani 1 1 d . . . . .
N1 N 0.38579(16) 0.5834(2) 0.07902(6) 0.0457(4) Uani 1 1 d . . . . .
H1 H 0.474013 0.529303 0.073946 0.055 Uiso 1 1 calc R U . . .
N2 N 0.33660(15) 0.6029(2) -0.03291(6) 0.0441(3) Uani 1 1 d . . . . .
N3 N 0.20769(16) 0.6676(2) -0.07167(6) 0.0458(4) Uani 1 1 d . . . . .
C1 C 0.6358(2) 0.7038(3) 0.16757(9) 0.0628(5) Uani 1 1 d . . . . .
H1A H 0.697447 0.759634 0.202198 0.094 Uiso 1 1 calc R U . . .
H1B H 0.637019 0.781284 0.130503 0.094 Uiso 1 1 calc R U . . .
H1C H 0.679354 0.585673 0.158101 0.094 Uiso 1 1 calc R U . . .
C2 C 0.4694(2) 0.6801(2) 0.18618(8) 0.0477(4) Uani 1 1 d . . . . .
C3 C 0.4292(3) 0.7199(3) 0.24818(8) 0.0600(5) Uani 1 1 d . . . . .
H3 H 0.507260 0.760909 0.277705 0.072 Uiso 1 1 calc R U . . .
C4 C 0.2786(3) 0.7006(3) 0.26724(9) 0.0711(6) Uani 1 1 d . . . . .
H4 H 0.255655 0.729311 0.308892 0.085 Uiso 1 1 calc R U . . .
C5 C 0.1610(3) 0.6382(3) 0.22412(9) 0.0677(6) Uani 1 1 d . . . . .
H5 H 0.058947 0.624119 0.236816 0.081 Uiso 1 1 calc R U . . .
C6 C 0.1957(2) 0.5969(3) 0.16199(8) 0.0521(4) Uani 1 1 d . . . . .
H6 H 0.117223 0.553701 0.133071 0.062 Uiso 1 1 calc R U . . .
C7 C 0.3487(2) 0.6201(2) 0.14290(7) 0.0415(4) Uani 1 1 d . . . . .
C8 C 0.29773(17) 0.6242(2) 0.02581(7) 0.0361(3) Uani 1 1 d . . . . .
C9 C 0.10392(17) 0.7222(2) -0.03396(6) 0.0365(3) Uani 1 1 d . . . . .
C10 C -0.05191(17) 0.7972(2) -0.04975(7) 0.0377(3) Uani 1 1 d . . . . .
C11 C -0.0905(2) 0.8564(2) -0.11179(8) 0.0484(4) Uani 1 1 d . . . . .
H11 H -0.014834 0.854778 -0.141983 0.058 Uiso 1 1 calc R U . . .
C12 C -0.2411(2) 0.9178(3) -0.12876(9) 0.0558(5) Uani 1 1 d . . . . .
H12 H -0.266414 0.957608 -0.170261 0.067 Uiso 1 1 calc R U . . .
C13 C -0.3533(2) 0.9198(3) -0.08435(10) 0.0570(5) Uani 1 1 d . . . . .
H13 H -0.455232 0.957808 -0.096130 0.068 Uiso 1 1 calc R U . . .
C14 C -0.3151(2) 0.8658(3) -0.02244(10) 0.0547(5) Uani 1 1 d . . . . .
H14 H -0.391106 0.869630 0.007602 0.066 Uiso 1 1 calc R U . . .
C15 C -0.16431(19) 0.8057(2) -0.00449(8) 0.0450(4) Uani 1 1 d . . . . .
H15 H -0.138623 0.771312 0.037560 0.054 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
O1 C8 1.3566(17) . ?
O1 C9 1.3761(17) . ?
N1 C8 1.340(2) . ?
N1 C7 1.4201(18) . ?
N1 H1 0.8600 . ?
N2 C8 1.3032(18) . ?
N2 N3 1.4070(18) . ?
N3 C9 1.2833(19) . ?
C1 C2 1.502(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.394(2) . ?
C2 C7 1.400(2) . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.395(2) . ?
C6 H6 0.9300 . ?
C9 C10 1.454(2) . ?
C10 C15 1.389(2) . ?
C10 C11 1.391(2) . ?
C11 C12 1.384(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.387(2) . ?
C14 H14 0.9300 . ?
C15 H15 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
C8 O1 C9 102.69(10) . . ?
C8 N1 C7 126.81(13) . . ?
C8 N1 H1 116.6 . . ?
C7 N1 H1 116.6 . . ?
C8 N2 N3 105.83(12) . . ?
C9 N3 N2 106.82(12) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 117.19(17) . . ?
C3 C2 C1 120.45(17) . . ?
C7 C2 C1 122.35(15) . . ?
C4 C3 C2 122.42(19) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C3 C4 C5 119.64(17) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 119.9(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 119.91(18) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 120.91(15) . . ?
C6 C7 N1 120.80(15) . . ?
C2 C7 N1 118.28(15) . . ?
N2 C8 N1 126.84(14) . . ?
N2 C8 O1 112.46(13) . . ?
N1 C8 O1 120.70(12) . . ?
N3 C9 O1 112.18(13) . . ?
N3 C9 C10 128.90(14) . . ?
O1 C9 C10 118.88(12) . . ?
C15 C10 C11 119.43(15) . . ?
C15 C10 C9 121.19(14) . . ?
C11 C10 C9 119.35(13) . . ?
C12 C11 C10 120.24(16) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 120.03(17) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.13(17) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 120.54(17) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 119.56(16) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?

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
C8 N2 N3 C9 0.26(18) . . . . ?
C7 C2 C3 C4 0.5(3) . . . . ?
C1 C2 C3 C4 179.85(19) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C5 C6 C7 C2 1.8(3) . . . . ?
C5 C6 C7 N1 -178.25(16) . . . . ?
C3 C2 C7 C6 -1.7(2) . . . . ?
C1 C2 C7 C6 179.02(17) . . . . ?
C3 C2 C7 N1 178.37(14) . . . . ?
C1 C2 C7 N1 -1.0(2) . . . . ?
C8 N1 C7 C6 40.0(2) . . . . ?
C8 N1 C7 C2 -140.00(17) . . . . ?
N3 N2 C8 N1 -179.04(15) . . . . ?
N3 N2 C8 O1 0.37(18) . . . . ?
C7 N1 C8 N2 174.55(16) . . . . ?
C7 N1 C8 O1 -4.8(2) . . . . ?
C9 O1 C8 N2 -0.81(16) . . . . ?
C9 O1 C8 N1 178.64(14) . . . . ?
N2 N3 C9 O1 -0.80(18) . . . . ?
N2 N3 C9 C10 -178.52(15) . . . . ?
C8 O1 C9 N3 0.99(17) . . . . ?
C8 O1 C9 C10 178.96(13) . . . . ?
N3 C9 C10 C15 163.26(16) . . . . ?
O1 C9 C10 C15 -14.3(2) . . . . ?
N3 C9 C10 C11 -14.8(3) . . . . ?
O1 C9 C10 C11 167.57(14) . . . . ?
C15 C10 C11 C12 -2.1(2) . . . . ?
C9 C10 C11 C12 176.09(15) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 C14 1.8(3) . . . . ?
C12 C13 C14 C15 -1.2(3) . . . . ?
C13 C14 C15 C10 -1.1(3) . . . . ?
C11 C10 C15 C14 2.7(2) . . . . ?
C9 C10 C15 C14 -175.42(15) . . . . ?

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
_geom_hbond_publ_flag
N1 H1 N2 0.86 2.10 2.9373(19) 162.8 3_665 yes

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.044



