# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_089HVE23
_database_code_depnum_ccdc_archive 'CCDC 2267235'
loop_
_audit_author_name
_audit_author_address
'Diego Martinez Otero'
;UNAM
Mexico
;
_audit_update_record             
;
2023-06-02 deposited with the CCDC.	2023-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        
3-(4-(4-chlorophenyl)-5-methyl-1H-pyrazol-3-yl)pyridine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 Cl N3'
_chemical_formula_weight         269.73

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'
Cl Cl 0.1484 0.1585 '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                   14.1324(5)
_cell_length_b                   8.3919(3)
_cell_length_c                   11.1269(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.5870(10)
_cell_angle_gamma                90
_cell_volume                     1282.69(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9903
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      27.95

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.208
_exptl_absorpt_coefficient_mu    0.286
_shelx_estimated_absorpt_T_min   0.904
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7186
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_absorpt_special_details   
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71077   11.146    8.404   14.156   90.008  103.603   90.012
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec ImuS'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18891
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.844
_diffrn_reflns_theta_max         27.948
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3087
_reflns_number_gt                2890
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    
; 
Ortep-3 Ver 2.02 L.J. Farrugia (1997) J. Appl. Cryst. 30, 565 
;
_computing_publication_material  'SHELXTL  (Sheldrick, 2013)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²+0.6530P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3087
_refine_ls_number_parameters     176
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0861
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.50306(2) 0.18675(4) 0.32135(3) 0.02154(10) Uani 1 1 d . . . . .
N1 N 0.11918(7) 0.19754(11) 0.56949(9) 0.0158(2) Uani 1 1 d . . . . .
C2 C 0.14294(8) 0.33845(13) 0.52870(10) 0.0140(2) Uani 1 1 d . . . . .
H2 H 0.169707 0.339610 0.457970 0.017 Uiso 1 1 calc R U . . .
C3 C 0.13070(7) 0.48398(13) 0.58402(10) 0.0122(2) Uani 1 1 d . . . . .
C4 C 0.08660(8) 0.48009(13) 0.68421(10) 0.0149(2) Uani 1 1 d . . . . .
H4 H 0.075390 0.576266 0.723717 0.018 Uiso 1 1 calc R U . . .
C5 C 0.05933(8) 0.33506(14) 0.72553(11) 0.0170(2) Uani 1 1 d . . . . .
H5 H 0.028125 0.330393 0.792325 0.020 Uiso 1 1 calc R U . . .
C6 C 0.07871(8) 0.19689(14) 0.66701(11) 0.0171(2) Uani 1 1 d . . . . .
H6 H 0.062545 0.097282 0.697503 0.021 Uiso 1 1 calc R U . . .
C7 C 0.30093(8) 0.54537(13) 0.43412(10) 0.0130(2) Uani 1 1 d . . . . .
C8 C 0.36346(8) 0.45173(13) 0.52270(10) 0.0145(2) Uani 1 1 d . . . . .
H8 H 0.363740 0.464492 0.607613 0.017 Uiso 1 1 calc R U . . .
C9 C 0.42507(8) 0.34057(13) 0.48859(10) 0.0155(2) Uani 1 1 d . . . . .
H9 H 0.467378 0.277704 0.549310 0.019 Uiso 1 1 calc R U . . .
C10 C 0.42371(8) 0.32293(13) 0.36404(10) 0.0148(2) Uani 1 1 d . . . . .
C11 C 0.36230(8) 0.41291(14) 0.27398(10) 0.0165(2) Uani 1 1 d . . . . .
H11 H 0.361851 0.398749 0.189136 0.020 Uiso 1 1 calc R U . . .
C12 C 0.30128(8) 0.52438(13) 0.30966(10) 0.0158(2) Uani 1 1 d . . . . .
H12 H 0.259261 0.587082 0.248513 0.019 Uiso 1 1 calc R U . . .
N11 N 0.16579(7) 0.88488(11) 0.50799(9) 0.01506(19) Uani 1 1 d D . . . .
H11A H 0.1504(11) 0.9876(11) 0.5179(14) 0.018 Uiso 1 1 d D U . . .
N12 N 0.12123(7) 0.77198(11) 0.56197(9) 0.01438(19) Uani 1 1 d . . . . .
C13 C 0.16284(8) 0.63502(13) 0.53968(10) 0.0126(2) Uani 1 1 d . . . . .
C14 C 0.23490(8) 0.66170(13) 0.47181(10) 0.0129(2) Uani 1 1 d . . . . .
C15 C 0.23437(8) 0.82521(13) 0.45385(10) 0.0144(2) Uani 1 1 d . . . . .
C16 C 0.29687(9) 0.92887(14) 0.39494(11) 0.0194(2) Uani 1 1 d . . . . .
H16A H 0.276019 1.040042 0.396726 0.029 Uiso 1 1 calc R U . . .
H16B H 0.290568 0.895458 0.309022 0.029 Uiso 1 1 calc R U . . .
H16C H 0.364956 0.918999 0.440472 0.029 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
Cl1 C10 1.7434(11) . ?
N1 C2 1.3374(14) . ?
N1 C6 1.3402(15) . ?
C2 C3 1.3965(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.3996(15) . ?
C3 C13 1.4703(14) . ?
C4 C5 1.3872(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.3882(16) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.3972(15) . ?
C7 C8 1.4002(15) . ?
C7 C14 1.4778(14) . ?
C8 C9 1.3883(15) . ?
C8 H8 0.9500 . ?
C9 C10 1.3894(15) . ?
C9 H9 0.9500 . ?
C10 C11 1.3853(16) . ?
C11 C12 1.3919(15) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
N11 C15 1.3518(14) . ?
N11 N12 1.3537(13) . ?
N11 H11A 0.902(9) . ?
N12 C13 1.3404(14) . ?
C13 C14 1.4209(15) . ?
C14 C15 1.3863(15) . ?
C15 C16 1.4962(15) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 N1 C6 117.86(10) . . ?
N1 C2 C3 123.82(10) . . ?
N1 C2 H2 118.1 . . ?
C3 C2 H2 118.1 . . ?
C2 C3 C4 117.07(10) . . ?
C2 C3 C13 121.74(9) . . ?
C4 C3 C13 121.19(10) . . ?
C5 C4 C3 119.66(10) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 118.46(10) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
N1 C6 C5 123.03(10) . . ?
N1 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
C12 C7 C8 118.58(10) . . ?
C12 C7 C14 120.93(10) . . ?
C8 C7 C14 120.48(9) . . ?
C9 C8 C7 121.15(10) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 118.79(10) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C10 C9 121.53(10) . . ?
C11 C10 Cl1 119.60(9) . . ?
C9 C10 Cl1 118.86(9) . . ?
C10 C11 C12 119.00(10) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C7 120.94(10) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
C15 N11 N12 113.29(9) . . ?
C15 N11 H11A 128.8(10) . . ?
N12 N11 H11A 117.6(10) . . ?
C13 N12 N11 104.36(9) . . ?
N12 C13 C14 111.32(10) . . ?
N12 C13 C3 119.58(9) . . ?
C14 C13 C3 129.10(10) . . ?
C15 C14 C13 104.61(9) . . ?
C15 C14 C7 126.54(10) . . ?
C13 C14 C7 128.75(10) . . ?
N11 C15 C14 106.41(10) . . ?
N11 C15 C16 122.60(10) . . ?
C14 C15 C16 130.91(10) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
C6 N1 C2 C3 1.99(17) . . . . ?
N1 C2 C3 C4 -3.16(16) . . . . ?
N1 C2 C3 C13 176.65(10) . . . . ?
C2 C3 C4 C5 1.39(16) . . . . ?
C13 C3 C4 C5 -178.42(10) . . . . ?
C3 C4 C5 C6 1.29(17) . . . . ?
C2 N1 C6 C5 1.00(17) . . . . ?
C4 C5 C6 N1 -2.61(18) . . . . ?
C12 C7 C8 C9 0.27(16) . . . . ?
C14 C7 C8 C9 179.21(10) . . . . ?
C7 C8 C9 C10 -0.15(17) . . . . ?
C8 C9 C10 C11 -0.27(17) . . . . ?
C8 C9 C10 Cl1 178.50(8) . . . . ?
C9 C10 C11 C12 0.56(17) . . . . ?
Cl1 C10 C11 C12 -178.21(9) . . . . ?
C10 C11 C12 C7 -0.43(17) . . . . ?
C8 C7 C12 C11 0.02(16) . . . . ?
C14 C7 C12 C11 -178.91(10) . . . . ?
C15 N11 N12 C13 -0.68(12) . . . . ?
N11 N12 C13 C14 0.46(12) . . . . ?
N11 N12 C13 C3 -179.06(9) . . . . ?
C2 C3 C13 N12 156.23(10) . . . . ?
C4 C3 C13 N12 -23.97(15) . . . . ?
C2 C3 C13 C14 -23.19(17) . . . . ?
C4 C3 C13 C14 156.61(11) . . . . ?
N12 C13 C14 C15 -0.10(12) . . . . ?
C3 C13 C14 C15 179.36(10) . . . . ?
N12 C13 C14 C7 176.49(10) . . . . ?
C3 C13 C14 C7 -4.05(19) . . . . ?
C12 C7 C14 C15 -62.06(16) . . . . ?
C8 C7 C14 C15 119.03(13) . . . . ?
C12 C7 C14 C13 122.05(13) . . . . ?
C8 C7 C14 C13 -56.86(16) . . . . ?
N12 N11 C15 C14 0.63(13) . . . . ?
N12 N11 C15 C16 -176.38(10) . . . . ?
C13 C14 C15 N11 -0.30(12) . . . . ?
C7 C14 C15 N11 -176.99(10) . . . . ?
C13 C14 C15 C16 176.37(11) . . . . ?
C7 C14 C15 C16 -0.32(19) . . . . ?

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
N11 H11A N1 0.902(9) 1.936(9) 2.8282(13) 169.9(14) 1_565 yes

_refine_diff_density_max         0.407
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.049


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
