# Electronic Supplementary Material (ESI) for Sensors & Diagnostics.
# 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_mo_sb_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2254070'
loop_
_audit_author_name
_audit_author_address
'Mr. Ramling Shivanandyya Mathpati '
;National Institute of Technology Kurukshetra Haryana 
India
;
_audit_update_record             
;
2023-04-05 deposited with the CCDC.	2023-07-05 downloaded from the CCDC.
;
_audit_creation_date             2023-04-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ApN3
_chemical_name_systematic        
2-azido-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide
_chemical_formula_moiety         'C13 H14 N6 O2'
_chemical_formula_sum            'C13 H14 N6 O2'
_chemical_formula_weight         286.30
_chemical_melting_point          158
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'

_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                   13.3072(7)
_cell_length_b                   6.9369(3)
_cell_length_c                   15.2738(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.507(2)
_cell_angle_gamma                90
_cell_volume                     1351.82(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.02
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.6642
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0871
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            92555
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.111
_diffrn_reflns_theta_min         2.397
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4086
_reflns_number_total             5503
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         5503
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0502P)²+0.4558P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1143
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C7(H7), C11(H11), C8(H8), C10(H10), C9(H9)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.38338(5) 0.55056(10) 0.71752(5) 0.01600(14) Uani 1 1 d . . . . .
O2 O 0.15151(6) 0.51476(11) 0.56191(5) 0.01892(15) Uani 1 1 d . . . . .
N3 N 0.20070(6) 0.26461(12) 0.66143(5) 0.01341(15) Uani 1 1 d . . . . .
H3 H 0.182063 0.186335 0.699401 0.016 Uiso 1 1 calc R U . . .
N1 N 0.46753(6) 0.31788(11) 0.65499(5) 0.01215(15) Uani 1 1 d . . . . .
N2 N 0.44005(6) 0.14376(11) 0.60697(5) 0.01309(15) Uani 1 1 d . . . . .
N4 N -0.00041(7) 0.58140(14) 0.66463(6) 0.02008(18) Uani 1 1 d . . . . .
N5 N -0.01366(7) 0.71739(14) 0.61037(6) 0.02076(18) Uani 1 1 d . . . . .
C6 C 0.55936(7) 0.41925(13) 0.65358(6) 0.01166(16) Uani 1 1 d . . . . .
C2 C 0.30195(7) 0.24933(13) 0.64994(6) 0.01214(16) Uani 1 1 d . . . . .
C7 C 0.60984(7) 0.53249(14) 0.72855(6) 0.01354(17) Uani 1 1 d . . . . .
H7 H 0.584768 0.536456 0.780884 0.016 Uiso 1 1 calc R U . . .
C1 C 0.38307(7) 0.39173(13) 0.68013(6) 0.01165(16) Uani 1 1 d . . . . .
C11 C 0.59793(7) 0.40870(14) 0.57775(6) 0.01471(17) Uani 1 1 d . . . . .
H11 H 0.563682 0.330259 0.527073 0.018 Uiso 1 1 calc R U . . .
C12 C 0.13200(7) 0.39780(14) 0.61491(6) 0.01341(17) Uani 1 1 d . . . . .
N6 N -0.02983(10) 0.85735(16) 0.57064(8) 0.0356(3) Uani 1 1 d . . . . .
C3 C 0.33889(7) 0.10253(13) 0.60905(6) 0.01326(17) Uani 1 1 d . . . . .
C8 C 0.69730(7) 0.63966(14) 0.72597(7) 0.01761(19) Uani 1 1 d . . . . .
H8 H 0.731232 0.719334 0.776272 0.021 Uiso 1 1 calc R U . . .
C10 C 0.68672(8) 0.51350(15) 0.57666(7) 0.01837(19) Uani 1 1 d . . . . .
H10 H 0.714036 0.504819 0.525699 0.022 Uiso 1 1 calc R U . . .
C5 C 0.52144(7) -0.00681(14) 0.62828(7) 0.01535(17) Uani 1 1 d . . . . .
H5A H 0.575920 0.024795 0.598874 0.023 Uiso 1 1 calc R U . . .
H5B H 0.489920 -0.131407 0.605594 0.023 Uiso 1 1 calc R U . . .
H5C H 0.552625 -0.014001 0.694542 0.023 Uiso 1 1 calc R U . . .
C13 C 0.02501(7) 0.39269(15) 0.63229(7) 0.01606(18) Uani 1 1 d . . . . .
H13A H -0.029054 0.357860 0.575187 0.019 Uiso 1 1 calc R U . . .
H13B H 0.024804 0.292980 0.678614 0.019 Uiso 1 1 calc R U . . .
C4 C 0.28502(8) -0.07886(15) 0.56957(8) 0.0204(2) Uani 1 1 d . . . . .
H4A H 0.294351 -0.099932 0.508914 0.031 Uiso 1 1 calc R U . . .
H4B H 0.210097 -0.068620 0.564361 0.031 Uiso 1 1 calc R U . . .
H4C H 0.315149 -0.187474 0.609433 0.031 Uiso 1 1 calc R U . . .
C9 C 0.73534(8) 0.63079(15) 0.65016(8) 0.0197(2) Uani 1 1 d . . . . .
H9 H 0.794768 0.705184 0.648656 0.024 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 C1 1.2404(11) . ?
O2 C12 1.2248(11) . ?
N3 H3 0.8800 . ?
N3 C2 1.4113(11) . ?
N3 C12 1.3510(12) . ?
N1 N2 1.4065(11) . ?
N1 C6 1.4153(11) . ?
N1 C1 1.3851(11) . ?
N2 C3 1.3854(11) . ?
N2 C5 1.4730(12) . ?
N4 N5 1.2349(13) . ?
N4 C13 1.4721(14) . ?
N5 N6 1.1327(14) . ?
C6 C7 1.3937(13) . ?
C6 C11 1.3957(13) . ?
C2 C1 1.4391(13) . ?
C2 C3 1.3576(13) . ?
C7 H7 0.9500 . ?
C7 C8 1.3910(13) . ?
C11 H11 0.9500 . ?
C11 C10 1.3914(14) . ?
C12 C13 1.5211(13) . ?
C3 C4 1.4883(13) . ?
C8 H8 0.9500 . ?
C8 C9 1.3906(15) . ?
C10 H10 0.9500 . ?
C10 C9 1.3886(15) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C9 H9 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 N3 H3 119.6 . . ?
C12 N3 H3 119.6 . . ?
C12 N3 C2 120.88(8) . . ?
N2 N1 C6 121.10(7) . . ?
C1 N1 N2 110.55(7) . . ?
C1 N1 C6 126.34(8) . . ?
N1 N2 C5 115.33(7) . . ?
C3 N2 N1 106.01(7) . . ?
C3 N2 C5 120.45(8) . . ?
N5 N4 C13 117.18(8) . . ?
N6 N5 N4 169.59(11) . . ?
C7 C6 N1 118.96(8) . . ?
C7 C6 C11 120.42(8) . . ?
C11 C6 N1 120.61(8) . . ?
N3 C2 C1 124.36(8) . . ?
C3 C2 N3 126.64(8) . . ?
C3 C2 C1 109.00(8) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.33(9) . . ?
C8 C7 H7 120.3 . . ?
O1 C1 N1 124.01(8) . . ?
O1 C1 C2 131.40(8) . . ?
N1 C1 C2 104.55(8) . . ?
C6 C11 H11 120.1 . . ?
C10 C11 C6 119.75(9) . . ?
C10 C11 H11 120.1 . . ?
O2 C12 N3 124.18(8) . . ?
O2 C12 C13 121.03(8) . . ?
N3 C12 C13 114.79(8) . . ?
N2 C3 C4 121.63(8) . . ?
C2 C3 N2 109.69(8) . . ?
C2 C3 C4 128.68(8) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.36(9) . . ?
C9 C8 H8 119.8 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 C11 119.91(9) . . ?
C9 C10 H10 120.0 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C13 C12 110.70(8) . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.19(9) . . ?
C10 C9 H9 119.9 . . ?

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
O2 C12 C13 N4 -56.92(12) . . . . ?
N3 C2 C1 O1 -2.37(16) . . . . ?
N3 C2 C1 N1 180.00(8) . . . . ?
N3 C2 C3 N2 177.08(8) . . . . ?
N3 C2 C3 C4 -2.26(16) . . . . ?
N3 C12 C13 N4 123.53(9) . . . . ?
N1 N2 C3 C2 4.35(10) . . . . ?
N1 N2 C3 C4 -176.26(8) . . . . ?
N1 C6 C7 C8 -177.03(8) . . . . ?
N1 C6 C11 C10 178.28(9) . . . . ?
N2 N1 C6 C7 -151.05(8) . . . . ?
N2 N1 C6 C11 29.99(13) . . . . ?
N2 N1 C1 O1 -174.71(8) . . . . ?
N2 N1 C1 C2 3.14(10) . . . . ?
N5 N4 C13 C12 66.32(12) . . . . ?
C6 N1 N2 C3 -169.49(8) . . . . ?
C6 N1 N2 C5 54.53(11) . . . . ?
C6 N1 C1 O1 -10.87(14) . . . . ?
C6 N1 C1 C2 166.98(8) . . . . ?
C6 C7 C8 C9 -1.35(14) . . . . ?
C6 C11 C10 C9 -1.22(15) . . . . ?
C2 N3 C12 O2 -1.31(15) . . . . ?
C2 N3 C12 C13 178.23(8) . . . . ?
C7 C6 C11 C10 -0.66(14) . . . . ?
C7 C8 C9 C10 -0.52(15) . . . . ?
C1 N1 N2 C3 -4.67(10) . . . . ?
C1 N1 N2 C5 -140.65(8) . . . . ?
C1 N1 C6 C7 46.67(13) . . . . ?
C1 N1 C6 C11 -132.29(10) . . . . ?
C1 C2 C3 N2 -2.51(11) . . . . ?
C1 C2 C3 C4 178.15(9) . . . . ?
C11 C6 C7 C8 1.94(14) . . . . ?
C11 C10 C9 C8 1.81(15) . . . . ?
C12 N3 C2 C1 68.76(13) . . . . ?
C12 N3 C2 C3 -110.76(11) . . . . ?
C3 C2 C1 O1 177.22(10) . . . . ?
C3 C2 C1 N1 -0.41(10) . . . . ?
C5 N2 C3 C2 137.57(9) . . . . ?
C5 N2 C3 C4 -43.03(13) . . . . ?
C13 N4 N5 N6 174.9(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
