# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_ngm-298
_database_code_depnum_ccdc_archive 'CCDC 1954607'
loop_
_audit_author_name
_audit_author_address
'Ekaterina Mescheryakova'
;Institute of Petrochemistry and Catalysis
Russia
;
_audit_update_record             
;
2019-09-19 deposited with the CCDC.	2020-03-25 downloaded from the CCDC.
;
_audit_creation_date             2019-09-18
_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_systematic        
4-{[(3,5-dimethyl-1H-pyrazol-4-yl)methyl]sulfanyl}phenol
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H14 N2 O S'
_chemical_formula_sum            'C12 H14 N2 O S'
_chemical_formula_weight         234.31
_exptl_crystal_recrystallization_method 'Acetone: Methanol'
_chemical_melting_point          459
_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      293(2)
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'
S S 0.1246 0.1234 '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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yn'
_chemical_absolute_configuration ?
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.1997(11)
_cell_length_b                   7.7319(4)
_cell_length_c                   16.5888(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.914(5)
_cell_angle_gamma                90
_cell_volume                     2449.5(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1732
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7030
_cell_measurement_theta_min      2.4940
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             992.0
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5838
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.139
_diffrn_reflns_theta_min         2.133
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1709
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -40.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.4011   77.0000   60.0000 86

#__ type_ start__ end____ width___ exp.time_
  2 omega   -9.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       17.2605   77.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
  3 omega   47.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       17.2605   77.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega   -6.00   20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       17.2605   77.0000 -180.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0008367000
_diffrn_orient_matrix_UB_12      0.0802966000
_diffrn_orient_matrix_UB_13      -0.0208047000
_diffrn_orient_matrix_UB_21      0.0027556000
_diffrn_orient_matrix_UB_22      0.0443766000
_diffrn_orient_matrix_UB_23      0.0375955000
_diffrn_orient_matrix_UB_31      0.0370242000
_diffrn_orient_matrix_UB_32      -0.0015362000
_diffrn_orient_matrix_UB_33      0.0011444000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'Agilent Xcalibur'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2095
_reflns_number_total             2802
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2802
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.041
_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)+(0.0630P)²+0.8711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1323
_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:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), N2(H2), C11(H11), C14(H14), C10(H10)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
S8 S 0.07004(3) 0.55074(6) 0.10445(3) 0.0581(2) Uani 1 1 d . . . . .
O16 O 0.24490(7) 0.84994(18) 0.38518(8) 0.0458(3) Uani 1 1 d . . . . .
N1 N 0.16101(9) 1.0348(2) -0.00754(10) 0.0513(4) Uani 1 1 d . . . . .
C13 C 0.22730(9) 0.7835(2) 0.24553(11) 0.0416(4) Uani 1 1 d . . . . .
H13 H 0.269250 0.838621 0.238218 0.050 Uiso 1 1 calc R . . . .
N2 N 0.14719(8) 1.1127(2) 0.06199(10) 0.0463(4) Uani 1 1 d . . . . .
H2 H 0.167573 1.205495 0.080713 0.056 Uiso 1 1 calc R . . . .
C11 C 0.14305(10) 0.6882(3) 0.33289(12) 0.0467(5) Uani 1 1 d . . . . .
H11 H 0.128765 0.677450 0.384549 0.056 Uiso 1 1 calc R . . . .
C12 C 0.20455(9) 0.7747(2) 0.32197(11) 0.0387(4) Uani 1 1 d . . . . .
C9 C 0.12403(10) 0.6306(2) 0.18953(12) 0.0430(4) Uani 1 1 d . . . . .
C14 C 0.18748(10) 0.7103(2) 0.18009(11) 0.0434(4) Uani 1 1 d . . . . .
H14 H 0.203439 0.714424 0.129062 0.052 Uiso 1 1 calc R . . . .
C3 C 0.09777(10) 1.0281(2) 0.09855(11) 0.0416(4) Uani 1 1 d . . . . .
C5 C 0.11828(10) 0.8979(3) -0.01531(12) 0.0474(5) Uani 1 1 d . . . . .
C4 C 0.07741(9) 0.8890(2) 0.04954(11) 0.0402(4) Uani 1 1 d . . . . .
C7 C 0.02692(10) 0.7518(3) 0.06689(13) 0.0507(5) Uani 1 1 d . . . . .
H7A H -0.003322 0.726851 0.017774 0.061 Uiso 1 1 calc R . . . .
H7B H -0.002263 0.794331 0.106987 0.061 Uiso 1 1 calc R . . . .
C10 C 0.10297(10) 0.6181(3) 0.26709(13) 0.0504(5) Uani 1 1 d . . . . .
H10 H 0.061345 0.561832 0.274697 0.061 Uiso 1 1 calc R . . . .
C6 C 0.07680(13) 1.0859(3) 0.17827(14) 0.0629(6) Uani 1 1 d . . . . .
H6A H 0.105842 1.030137 0.221162 0.094 Uiso 1 1 calc GR . . . .
H6B H 0.028708 1.055905 0.181944 0.094 Uiso 1 1 calc GR . . . .
H6C H 0.082324 1.209016 0.183053 0.094 Uiso 1 1 calc GR . . . .
C15 C 0.12027(15) 0.7765(4) -0.08548(14) 0.0804(8) Uani 1 1 d . . . . .
H15A H 0.142517 0.832348 -0.127706 0.121 Uiso 1 1 calc GR . . . .
H15B H 0.073363 0.744575 -0.105640 0.121 Uiso 1 1 calc GR . . . .
H15C H 0.146200 0.674655 -0.068017 0.121 Uiso 1 1 calc GR . . . .
H16 H 0.2205(13) 0.884(4) 0.4266(15) 0.083(8) 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
S8 C9 1.7737(19) . ?
S8 C7 1.840(2) . ?
O16 C12 1.368(2) . ?
N1 N2 1.352(2) . ?
N1 C5 1.337(3) . ?
C13 C12 1.385(2) . ?
C13 C14 1.383(3) . ?
N2 C3 1.347(2) . ?
C11 C12 1.385(3) . ?
C11 C10 1.380(3) . ?
C9 C14 1.388(3) . ?
C9 C10 1.391(3) . ?
C3 C4 1.380(3) . ?
C3 C6 1.490(3) . ?
C5 C4 1.397(3) . ?
C5 C15 1.499(3) . ?
C4 C7 1.485(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
C9 S8 C7 100.42(9) . . ?
C5 N1 N2 105.22(15) . . ?
C14 C13 C12 119.84(17) . . ?
C3 N2 N1 112.16(16) . . ?
C10 C11 C12 119.97(17) . . ?
O16 C12 C13 118.28(17) . . ?
O16 C12 C11 121.89(16) . . ?
C13 C12 C11 119.82(17) . . ?
C14 C9 S8 120.82(15) . . ?
C14 C9 C10 118.49(17) . . ?
C10 C9 S8 120.67(15) . . ?
C13 C14 C9 120.91(17) . . ?
N2 C3 C4 106.44(17) . . ?
N2 C3 C6 121.40(18) . . ?
C4 C3 C6 132.12(18) . . ?
N1 C5 C4 110.64(17) . . ?
N1 C5 C15 120.41(19) . . ?
C4 C5 C15 128.9(2) . . ?
C3 C4 C5 105.54(17) . . ?
C3 C4 C7 126.39(18) . . ?
C5 C4 C7 127.88(18) . . ?
C4 C7 S8 112.91(13) . . ?
C11 C10 C9 120.85(18) . . ?


