# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_rk130a_1
_database_code_depnum_ccdc_archive 'CCDC 1978280'
loop_
_audit_author_name
_audit_author_address
'Malcolm Halcrow' 'University of Leeds'
_audit_update_record             
;
2020-01-16 deposited with the CCDC.	2020-05-26 downloaded from the CCDC.
;
_audit_creation_date             2020-01-16
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
4-(Isopropylsulfanyl)-2,6-di(pyrazol-1-yl)pyridine
;
_chemical_formula_moiety         'C14 H15 N5 S'
_chemical_formula_sum            'C14 H15 N5 S'
_chemical_formula_weight         285.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.2184(2)
_cell_length_b                   32.4625(16)
_cell_length_c                   10.1791(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.362(4)
_cell_angle_gamma                90.00
_cell_volume                     1392.74(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2158
_cell_measurement_temperature    120(2)
_cell_measurement_theta_min      5.11
_cell_measurement_theta_max      73.63
_exptl_absorpt_coefficient_mu    2.040
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 This dataset is only 89.5 % complete to /q = 72 deg, which reflects 
 incomplete data collection in the hk0 and 0kl zones. That?s a consequence of 
 the long unit cell b axis, and the crystal's needle morphology. Despite that 
 limitation, the observed data:parameter ratio is 12.3:1, which is easily 
 enough for a precise refinement. 
;
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4056
_diffrn_reflns_theta_full        72.00
_diffrn_reflns_theta_max         73.72
_diffrn_reflns_theta_min         4.56
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 5.3095
_diffrn_measured_fraction_theta_full 0.895
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_reflns_number_gt                2258
_reflns_number_total             2468
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2468
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0389P)²+1.6900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1140
_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 > 2sigma(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. 

 No disorder is present in the model, and no restraints were applied. 
 All non-H atoms were refined anisotropically, and H atoms were placed in 
 calculated positions and refined using a riding model.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.9417(4) 0.67532(6) 0.37007(18) 0.0168(4) Uani 1 1 d . . .
C2 C 1.0397(5) 0.63698(7) 0.3901(2) 0.0157(5) Uani 1 1 d . . .
C3 C 0.9728(5) 0.61238(7) 0.4970(2) 0.0172(5) Uani 1 1 d . . .
H3 H 1.0529 0.5851 0.5058 0.021 Uiso 1 1 calc R . .
C4 C 0.7818(5) 0.62982(7) 0.5907(2) 0.0156(4) Uani 1 1 d . . .
C5 C 0.6716(5) 0.66976(7) 0.5735(2) 0.0174(5) Uani 1 1 d . . .
H5 H 0.5399 0.6822 0.6358 0.021 Uiso 1 1 calc R . .
C6 C 0.7601(5) 0.69101(7) 0.4622(2) 0.0159(5) Uani 1 1 d . . .
N7 N 1.2304(4) 0.62088(6) 0.29022(18) 0.0172(4) Uani 1 1 d . . .
N8 N 1.3232(5) 0.58088(6) 0.29352(19) 0.0233(5) Uani 1 1 d . . .
C9 C 1.4857(6) 0.57659(8) 0.1857(2) 0.0258(5) Uani 1 1 d . . .
H9 H 1.5833 0.5516 0.1607 0.031 Uiso 1 1 calc R . .
C10 C 1.4975(6) 0.61314(8) 0.1125(2) 0.0240(5) Uani 1 1 d . . .
H10 H 1.5988 0.6175 0.0321 0.029 Uiso 1 1 calc R . .
C11 C 1.3304(6) 0.64104(8) 0.1829(2) 0.0203(5) Uani 1 1 d . . .
H11 H 1.2920 0.6691 0.1608 0.024 Uiso 1 1 calc R . .
N12 N 0.6558(4) 0.73153(6) 0.44023(18) 0.0173(4) Uani 1 1 d . . .
N13 N 0.4717(5) 0.75040(7) 0.52982(19) 0.0234(5) Uani 1 1 d . . .
C14 C 0.4195(6) 0.78745(8) 0.4804(2) 0.0251(5) Uani 1 1 d . . .
H14 H 0.2960 0.8079 0.5212 0.030 Uiso 1 1 calc R . .
C15 C 0.5679(6) 0.79325(8) 0.3601(2) 0.0247(5) Uani 1 1 d . . .
H15 H 0.5649 0.8173 0.3067 0.030 Uiso 1 1 calc R . .
C16 C 0.7166(6) 0.75674(8) 0.3374(2) 0.0213(5) Uani 1 1 d . . .
H16 H 0.8390 0.7502 0.2640 0.026 Uiso 1 1 calc R . .
S17 S 0.66952(13) 0.604677(17) 0.73465(5) 0.01822(17) Uani 1 1 d . . .
C18 C 0.8603(5) 0.55434(7) 0.7287(2) 0.0196(5) Uani 1 1 d . . .
H18 H 1.0840 0.5583 0.7024 0.023 Uiso 1 1 calc R . .
C19 C 0.6955(6) 0.52516(8) 0.6305(2) 0.0236(5) Uani 1 1 d . . .
H19A H 0.8234 0.5002 0.6221 0.035 Uiso 1 1 calc R . .
H19B H 0.6710 0.5387 0.5447 0.035 Uiso 1 1 calc R . .
H19C H 0.4860 0.5178 0.6615 0.035 Uiso 1 1 calc R . .
C20 C 0.8669(6) 0.53709(9) 0.8676(2) 0.0284(6) Uani 1 1 d . . .
H20A H 0.6498 0.5352 0.8978 0.043 Uiso 1 1 calc R . .
H20B H 0.9920 0.5553 0.9263 0.043 Uiso 1 1 calc R . .
H20C H 0.9633 0.5096 0.8682 0.043 Uiso 1 1 calc R . .


_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
N1 C2 1.325(3) . ?
N1 C6 1.336(3) . ?
C2 C3 1.388(3) . ?
C2 N7 1.422(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(3) . ?
C4 C5 1.386(3) . ?
C4 S17 1.759(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(3) . ?
C6 N12 1.402(3) . ?
N7 N8 1.356(3) . ?
N7 C11 1.356(3) . ?
N8 C9 1.325(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.403(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.368(3) . ?
C11 H11 0.9500 . ?
N12 N13 1.367(3) . ?
N12 C16 1.361(3) . ?
N13 C14 1.319(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.411(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.365(3) . ?
C16 H16 0.9500 . ?
S17 C18 1.824(2) . ?
C18 H18 1.0000 . ?
C18 C19 1.524(3) . ?
C18 C20 1.520(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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 115.74(19) . . ?
N1 C2 C3 126.1(2) . . ?
N1 C2 N7 114.68(19) . . ?
C3 C2 N7 119.2(2) . . ?
C2 C3 H3 121.8 . . ?
C2 C3 C4 116.4(2) . . ?
C4 C3 H3 121.8 . . ?
C3 C4 S17 124.38(18) . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 S17 116.01(16) . . ?
C4 C5 H5 121.1 . . ?
C4 C5 C6 117.8(2) . . ?
C6 C5 H5 121.1 . . ?
N1 C6 C5 124.3(2) . . ?
N1 C6 N12 115.51(19) . . ?
C5 C6 N12 120.2(2) . . ?
N8 N7 C2 120.37(18) . . ?
C11 N7 C2 127.1(2) . . ?
C11 N7 N8 112.51(19) . . ?
C9 N8 N7 103.81(19) . . ?
N8 C9 H9 123.8 . . ?
N8 C9 C10 112.4(2) . . ?
C10 C9 H9 123.8 . . ?
C9 C10 H10 127.7 . . ?
C11 C10 C9 104.6(2) . . ?
C11 C10 H10 127.7 . . ?
N7 C11 C10 106.7(2) . . ?
N7 C11 H11 126.7 . . ?
C10 C11 H11 126.7 . . ?
N13 N12 C6 119.81(18) . . ?
C16 N12 C6 128.25(19) . . ?
C16 N12 N13 111.94(19) . . ?
C14 N13 N12 104.16(19) . . ?
N13 C14 H14 123.8 . . ?
N13 C14 C15 112.3(2) . . ?
C15 C14 H14 123.8 . . ?
C14 C15 H15 127.6 . . ?
C16 C15 C14 104.7(2) . . ?
C16 C15 H15 127.6 . . ?
N12 C16 C15 106.8(2) . . ?
N12 C16 H16 126.6 . . ?
C15 C16 H16 126.6 . . ?
C4 S17 C18 104.69(11) . . ?
S17 C18 H18 108.4 . . ?
C19 C18 S17 112.88(17) . . ?
C19 C18 H18 108.4 . . ?
C20 C18 S17 106.88(17) . . ?
C20 C18 H18 108.4 . . ?
C20 C18 C19 111.8(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
N1 C2 C3 C4 0.7(3) . . . . ?
N1 C2 N7 N8 -174.4(2) . . . . ?
N1 C2 N7 C11 3.2(3) . . . . ?
N1 C6 N12 N13 -179.3(2) . . . . ?
N1 C6 N12 C16 -0.1(3) . . . . ?
C2 N1 C6 C5 -0.3(3) . . . . ?
C2 N1 C6 N12 -179.72(19) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C3 C4 S17 -179.34(17) . . . . ?
C2 N7 N8 C9 178.3(2) . . . . ?
C2 N7 C11 C10 -178.0(2) . . . . ?
C3 C2 N7 N8 5.6(3) . . . . ?
C3 C2 N7 C11 -176.8(2) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C3 C4 S17 C18 0.7(2) . . . . ?
C4 C5 C6 N1 0.7(3) . . . . ?
C4 C5 C6 N12 -179.9(2) . . . . ?
C4 S17 C18 C19 -75.35(18) . . . . ?
C4 S17 C18 C20 161.32(17) . . . . ?
C5 C4 S17 C18 -178.44(17) . . . . ?
C5 C6 N12 N13 1.2(3) . . . . ?
C5 C6 N12 C16 -179.6(2) . . . . ?
C6 N1 C2 C3 -0.5(3) . . . . ?
C6 N1 C2 N7 179.54(19) . . . . ?
C6 N12 N13 C14 179.5(2) . . . . ?
C6 N12 C16 C15 -179.2(2) . . . . ?
N7 C2 C3 C4 -179.3(2) . . . . ?
N7 N8 C9 C10 -0.3(3) . . . . ?
N8 N7 C11 C10 -0.2(3) . . . . ?
N8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 N7 0.0(3) . . . . ?
C11 N7 N8 C9 0.3(3) . . . . ?
N12 N13 C14 C15 -0.3(3) . . . . ?
N13 N12 C16 C15 0.0(3) . . . . ?
N13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 N12 -0.1(3) . . . . ?
C16 N12 N13 C14 0.2(3) . . . . ?
S17 C4 C5 C6 178.78(17) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
