2,4,6-Tris(pyridin-2-ylsulfan­yl)-1,3,5-triazine

Galicia-López, O.; Morales-Morales, D.; Hernández-Ortega, S.

doi:10.1107/S1600536807010045

2,4,6-Tris(pyridin-2-ylsulfanyl)-1,3,5-triazine

O. Galicia-López, D. Morales-Morales and S. Hernández-Ortega

There are two independent molecules in the asymmetric unit of the title compound, C₂₁H₁₈N₆S. The molecules are linked by C—H

S and C—H

N intermolecular and π–π stacking interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807010045/av3075sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807010045/av3075Isup2.hkl Contains datablock I

CCDC reference: 642902

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.007 Å
Disorder in main residue
R factor = 0.045
wR factor = 0.055
Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT480_ALERT_4_B Long H...A H-Bond Reported H16    ..  S4      ..       3.45 Ang.

Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S4
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S5
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S6
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C10
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C22
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT301_ALERT_3_C Main Residue  Disorder .........................      16.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17    ..  N10     ..       2.84 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11    ..  S4      ..       3.23 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H24    ..  S1      ..       2.98 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C16    ..  S4      ..       4.26 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               6608
           Count of symmetry unique reflns         3715
           Completeness (_total/calc)            177.87%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2893
           Fraction of Friedel pairs measured     0.779
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  15 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

2,4,6-tris(pyridin-2-ylsulfanyl)-1,3,5-triazine top

Crystal data top

C₁₈H₁₂N₆S₃	F(000) = 1680
M_r = 408.52	D_x = 1.441 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6733 reflections
a = 10.2018 (7) Å	θ = 2.2–31.3°
b = 16.7019 (11) Å	µ = 0.41 mm⁻¹
c = 22.1016 (14) Å	T = 298 K
V = 3765.9 (4) Å³	Prism, colourless
Z = 8	0.39 × 0.08 × 0.02 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3651 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.082
Graphite monochromator	θ_max = 25.0°, θ_min = 1.8°
ω scans	h = −12→12
30823 measured reflections	k = −19→19
6608 independent reflections	l = −26→26

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.055	w = 1/[σ²(F_o²) + (0.0112P)²] where P = (F_o² + 2F_c²)/3
S = 0.81	(Δ/σ)_max = 0.001
6608 reflections	Δρ_max = 0.37 e Å⁻³
579 parameters	Δρ_min = −0.19 e Å⁻³
402 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (5)

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.66448 (9)	1.08458 (6)	1.02430 (5)	0.0622 (3)
S2	0.69358 (11)	0.87064 (6)	0.84847 (5)	0.0756 (4)
S3	0.35688 (11)	0.84304 (6)	1.03282 (5)	0.0764 (4)
N1	0.5185 (3)	0.96146 (17)	1.01683 (12)	0.0521 (8)
N2	0.6679 (3)	0.97323 (16)	0.93498 (13)	0.0490 (8)
N3	0.5252 (3)	0.85927 (16)	0.94098 (14)	0.0511 (8)
N4	0.8490 (3)	1.18454 (17)	1.02521 (13)	0.0600 (9)
N5	0.6671 (3)	0.7139 (2)	0.84360 (16)	0.0847 (12)
N6	0.2405 (4)	0.7470 (2)	0.95585 (18)	0.0816 (11)
C1	0.6145 (3)	0.9973 (2)	0.98621 (17)	0.0456 (10)
C2	0.6186 (3)	0.9026 (2)	0.91523 (15)	0.0496 (10)
C3	0.4795 (3)	0.8922 (2)	0.99140 (17)	0.0512 (10)
C4	0.8112 (3)	1.1221 (2)	0.99236 (17)	0.0500 (10)
C5	0.9624 (4)	1.2202 (2)	1.00947 (19)	0.0672 (13)
H5	0.9900	1.2641	1.0321	0.081*
C6	1.0397 (4)	1.1958 (2)	0.9620 (2)	0.0673 (12)
H6	1.1179	1.2217	0.9530	0.081*
C7	0.9977 (4)	1.1321 (3)	0.92842 (19)	0.0822 (14)
H7	1.0468	1.1141	0.8957	0.099*
C8	0.8823 (4)	1.0950 (2)	0.94357 (17)	0.0703 (12)
H8	0.8523	1.0518	0.9210	0.084*
C9	0.6037 (4)	0.7817 (2)	0.83222 (17)	0.0555 (11)
C10	0.6019 (5)	0.6463 (3)	0.8296 (2)	0.1054 (18)
H10	0.6426	0.5974	0.8371	0.126*
C11	0.4796 (6)	0.6458 (3)	0.8050 (2)	0.0888 (17)
H11	0.4384	0.5977	0.7957	0.107*
C12	0.4190 (5)	0.7163 (3)	0.79453 (19)	0.0919 (15)
H12	0.3352	0.7177	0.7780	0.110*
C13	0.4829 (4)	0.7855 (2)	0.80860 (18)	0.0724 (13)
H13	0.4431	0.8348	0.8019	0.087*
C14	0.3430 (5)	0.7519 (3)	0.99206 (19)	0.0652 (12)
C15	0.2254 (5)	0.6773 (4)	0.9259 (2)	0.0963 (17)
H15	0.1533	0.6717	0.9005	0.116*
C16	0.3104 (6)	0.6148 (3)	0.9309 (2)	0.0992 (19)
H16	0.2965	0.5681	0.9089	0.119*
C17	0.4140 (5)	0.6208 (3)	0.9678 (2)	0.1011 (17)
H17	0.4727	0.5786	0.9720	0.121*
C18	0.4317 (4)	0.6916 (3)	0.9996 (2)	0.0874 (15)
H18	0.5027	0.6978	1.0256	0.105*
S4	0.43380 (10)	0.41028 (6)	0.83088 (5)	0.0754 (3)
S5	0.43065 (10)	0.09853 (6)	0.85965 (5)	0.0733 (3)
S6	0.02308 (10)	0.25983 (7)	0.76507 (5)	0.0850 (4)
N7	0.2383 (3)	0.32149 (18)	0.80228 (13)	0.0561 (9)
N8	0.4200 (3)	0.24996 (19)	0.84198 (12)	0.0517 (8)
N9	0.2262 (3)	0.17960 (17)	0.81236 (13)	0.0509 (8)
N10	0.6030 (3)	0.45151 (19)	0.91112 (18)	0.0793 (11)
C19	0.3584 (4)	0.3164 (2)	0.82505 (16)	0.0537 (10)
C20	0.3471 (4)	0.1838 (2)	0.83490 (16)	0.0482 (10)
C21	0.1795 (3)	0.2514 (3)	0.79641 (15)	0.0517 (10)
C22	0.5828 (4)	0.3956 (2)	0.87041 (18)	0.0565 (11)
C23	0.7145 (5)	0.4458 (3)	0.9417 (2)	0.1017 (18)
H23	0.7324	0.4852	0.9702	0.122*
C24	0.8044 (5)	0.3865 (3)	0.9344 (3)	0.1009 (18)
H24	0.8791	0.3850	0.9585	0.121*
C25	0.7845 (4)	0.3304 (3)	0.8921 (2)	0.0878 (15)
H25	0.8451	0.2897	0.8855	0.105*
C26	0.6712 (4)	0.3353 (2)	0.85875 (19)	0.0732 (12)
H26	0.6543	0.2981	0.8285	0.088*
C27	0.3125 (4)	0.02178 (19)	0.85014 (18)	0.0628 (11)
N11	0.2841 (7)	−0.0156 (4)	0.9021 (2)	0.0732 (17)	0.713 (12)
C28	0.1976 (9)	−0.0758 (4)	0.8970 (3)	0.087 (2)	0.713 (12)
H28	0.1715	−0.1012	0.9324	0.105*	0.713 (12)
C29	0.1449 (7)	−0.1027 (4)	0.8443 (3)	0.086 (2)	0.713 (12)
H29	0.0898	−0.1470	0.8437	0.103*	0.713 (12)
C30	0.1764 (8)	−0.0615 (4)	0.7912 (3)	0.085 (2)	0.713 (12)
H30	0.1378	−0.0753	0.7545	0.102*	0.713 (12)
C31	0.2661 (8)	−0.0001 (4)	0.7946 (2)	0.0760 (19)	0.713 (12)
H31	0.2944	0.0259	0.7598	0.091*	0.713 (12)
N11A	0.2320 (14)	0.0089 (8)	0.8970 (5)	0.076 (2)	0.287 (12)
C28A	0.1375 (14)	−0.0463 (9)	0.8874 (7)	0.082 (2)	0.287 (12)
H28A	0.0816	−0.0581	0.9194	0.098*	0.287 (12)
C29A	0.1181 (15)	−0.0859 (10)	0.8343 (8)	0.085 (3)	0.287 (12)
H29A	0.0422	−0.1152	0.8272	0.102*	0.287 (12)
C30A	0.2177 (16)	−0.0804 (10)	0.7910 (7)	0.084 (3)	0.287 (12)
H30A	0.2230	−0.1168	0.7592	0.101*	0.287 (12)
C31A	0.3080 (15)	−0.0193 (9)	0.7969 (5)	0.074 (3)	0.287 (12)
H31A	0.3644	−0.0065	0.7652	0.088*	0.287 (12)
C32	−0.0228 (4)	0.1608 (2)	0.7477 (2)	0.0698 (11)
N12	−0.1250 (13)	0.1448 (7)	0.7840 (6)	0.089 (2)	0.513 (16)
C33	−0.1728 (11)	0.0700 (7)	0.7766 (6)	0.091 (2)	0.513 (16)
H33	−0.2386	0.0534	0.8029	0.109*	0.513 (16)
C34	−0.1325 (13)	0.0166 (5)	0.7337 (7)	0.084 (2)	0.513 (16)
H34	−0.1675	−0.0347	0.7320	0.100*	0.513 (16)
C35	−0.0372 (13)	0.0412 (5)	0.6924 (5)	0.084 (2)	0.513 (16)
H35	−0.0124	0.0086	0.6603	0.101*	0.513 (16)
C36	0.0189 (16)	0.1156 (7)	0.7008 (7)	0.078 (2)	0.513 (16)
H36	0.0839	0.1341	0.6749	0.093*	0.513 (16)
N12A	−0.1134 (14)	0.1201 (7)	0.7793 (6)	0.092 (2)	0.487 (16)
C33A	−0.1484 (15)	0.0492 (7)	0.7552 (7)	0.095 (2)	0.487 (16)
H33A	−0.2185	0.0226	0.7731	0.115*	0.487 (16)
C34A	−0.0906 (13)	0.0130 (5)	0.7072 (7)	0.083 (3)	0.487 (16)
H34A	−0.1179	−0.0370	0.6936	0.100*	0.487 (16)
C35A	0.0114 (13)	0.0540 (6)	0.6789 (5)	0.079 (2)	0.487 (16)
H35A	0.0552	0.0316	0.6461	0.095*	0.487 (16)
C36A	0.0462 (17)	0.1284 (8)	0.7006 (7)	0.075 (2)	0.487 (16)
H36A	0.1158	0.1563	0.6835	0.090*	0.487 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0570 (7)	0.0494 (6)	0.0803 (8)	−0.0088 (6)	0.0111 (6)	−0.0195 (6)
S2	0.0882 (9)	0.0669 (8)	0.0717 (8)	−0.0294 (7)	0.0265 (7)	−0.0196 (6)
S3	0.0755 (8)	0.0610 (7)	0.0929 (9)	−0.0218 (6)	0.0314 (7)	−0.0159 (7)
N1	0.051 (2)	0.048 (2)	0.057 (2)	−0.0010 (17)	0.0082 (18)	−0.0116 (18)
N2	0.057 (2)	0.0364 (18)	0.054 (2)	−0.0047 (16)	0.0033 (18)	−0.0010 (16)
N3	0.054 (2)	0.0438 (19)	0.056 (2)	−0.0076 (17)	0.0059 (17)	−0.0053 (17)
N4	0.063 (2)	0.045 (2)	0.072 (2)	−0.0124 (18)	0.003 (2)	−0.0112 (19)
N5	0.088 (3)	0.062 (2)	0.104 (3)	−0.002 (2)	0.005 (2)	0.007 (3)
N6	0.076 (3)	0.064 (3)	0.105 (3)	−0.018 (2)	0.012 (2)	−0.015 (3)
C1	0.039 (2)	0.042 (2)	0.055 (3)	0.0035 (19)	0.007 (2)	−0.001 (2)
C2	0.056 (3)	0.041 (2)	0.052 (3)	−0.006 (2)	−0.009 (2)	0.002 (2)
C3	0.055 (3)	0.045 (3)	0.053 (3)	−0.006 (2)	0.000 (2)	−0.006 (2)
C4	0.051 (3)	0.040 (2)	0.059 (3)	0.003 (2)	−0.007 (2)	−0.001 (2)
C5	0.077 (3)	0.051 (3)	0.073 (3)	−0.020 (3)	−0.008 (3)	0.005 (2)
C6	0.062 (3)	0.067 (3)	0.073 (3)	−0.007 (3)	0.003 (3)	0.001 (3)
C7	0.070 (3)	0.077 (3)	0.099 (4)	−0.018 (3)	0.021 (3)	−0.017 (3)
C8	0.066 (3)	0.065 (3)	0.080 (3)	−0.025 (3)	0.013 (3)	−0.027 (3)
C9	0.064 (3)	0.050 (3)	0.052 (3)	−0.013 (2)	0.016 (2)	−0.004 (2)
C10	0.116 (5)	0.062 (4)	0.138 (5)	−0.001 (4)	0.026 (4)	−0.004 (4)
C11	0.130 (5)	0.057 (4)	0.079 (4)	−0.043 (4)	0.012 (4)	−0.003 (3)
C12	0.094 (4)	0.101 (4)	0.080 (3)	−0.040 (4)	−0.024 (3)	0.016 (3)
C13	0.075 (3)	0.053 (3)	0.089 (4)	−0.014 (3)	−0.008 (3)	0.011 (3)
C14	0.057 (3)	0.059 (3)	0.079 (3)	−0.020 (3)	0.023 (3)	−0.001 (3)
C15	0.079 (4)	0.104 (4)	0.105 (4)	−0.046 (4)	0.020 (3)	−0.020 (4)
C16	0.119 (5)	0.064 (4)	0.115 (5)	−0.038 (4)	0.046 (4)	−0.020 (4)
C17	0.115 (5)	0.055 (4)	0.134 (5)	−0.013 (3)	0.023 (4)	−0.005 (3)
C18	0.089 (4)	0.052 (3)	0.121 (4)	−0.010 (3)	0.007 (3)	−0.005 (3)
S4	0.0800 (8)	0.0447 (6)	0.1014 (9)	−0.0023 (6)	−0.0296 (7)	0.0054 (7)
S5	0.0735 (7)	0.0528 (7)	0.0935 (9)	0.0073 (6)	−0.0247 (7)	0.0156 (7)
S6	0.0631 (7)	0.0660 (8)	0.1259 (11)	0.0086 (7)	−0.0313 (7)	0.0023 (7)
N7	0.065 (2)	0.043 (2)	0.060 (2)	0.0078 (19)	−0.0153 (19)	0.0031 (18)
N8	0.0596 (19)	0.0445 (18)	0.051 (2)	0.0073 (19)	−0.0097 (17)	0.0067 (18)
N9	0.045 (2)	0.046 (2)	0.062 (2)	0.0034 (17)	−0.0003 (17)	0.0054 (17)
N10	0.070 (3)	0.052 (2)	0.116 (3)	−0.008 (2)	−0.020 (3)	−0.008 (2)
C19	0.064 (3)	0.045 (3)	0.051 (3)	−0.004 (2)	−0.012 (2)	0.004 (2)
C20	0.056 (3)	0.045 (3)	0.044 (2)	0.007 (2)	0.008 (2)	0.003 (2)
C21	0.056 (3)	0.050 (2)	0.049 (3)	0.009 (3)	−0.003 (2)	−0.004 (2)
C22	0.064 (3)	0.040 (2)	0.066 (3)	−0.013 (2)	−0.010 (2)	0.004 (2)
C23	0.086 (4)	0.081 (4)	0.138 (5)	−0.026 (3)	−0.040 (4)	−0.026 (3)
C24	0.059 (3)	0.083 (4)	0.160 (6)	−0.011 (3)	−0.035 (4)	0.009 (4)
C25	0.055 (3)	0.077 (4)	0.131 (5)	−0.004 (3)	−0.015 (3)	−0.001 (3)
C26	0.057 (3)	0.072 (3)	0.091 (3)	−0.007 (3)	0.005 (3)	−0.016 (3)
C27	0.082 (3)	0.040 (2)	0.067 (3)	0.013 (2)	−0.018 (2)	0.011 (2)
N11	0.096 (4)	0.049 (3)	0.075 (3)	0.003 (3)	−0.014 (3)	0.014 (2)
C28	0.113 (5)	0.057 (4)	0.091 (3)	−0.005 (3)	−0.015 (3)	0.019 (3)
C29	0.103 (4)	0.049 (3)	0.105 (4)	−0.006 (3)	−0.030 (3)	0.013 (3)
C30	0.107 (4)	0.056 (4)	0.090 (3)	0.009 (3)	−0.040 (3)	0.001 (3)
C31	0.100 (4)	0.055 (4)	0.074 (3)	0.005 (3)	−0.018 (3)	0.014 (3)
N11A	0.099 (5)	0.052 (5)	0.076 (4)	0.002 (4)	−0.009 (4)	0.010 (4)
C28A	0.105 (5)	0.054 (5)	0.087 (4)	0.000 (4)	−0.011 (4)	0.016 (4)
C29A	0.106 (5)	0.053 (5)	0.097 (5)	−0.007 (4)	−0.022 (4)	0.010 (4)
C30A	0.104 (5)	0.055 (5)	0.092 (4)	0.006 (4)	−0.022 (4)	−0.006 (4)
C31A	0.098 (5)	0.047 (5)	0.077 (4)	0.010 (5)	−0.013 (4)	0.003 (4)
C32	0.052 (3)	0.067 (3)	0.091 (3)	−0.009 (2)	−0.026 (2)	0.016 (2)
N12	0.073 (4)	0.069 (5)	0.125 (4)	−0.013 (4)	−0.009 (3)	0.017 (4)
C33	0.074 (5)	0.072 (5)	0.127 (5)	−0.014 (4)	−0.006 (4)	0.010 (4)
C34	0.072 (5)	0.065 (4)	0.114 (6)	−0.023 (4)	−0.011 (4)	0.013 (4)
C35	0.073 (6)	0.069 (4)	0.110 (5)	−0.039 (4)	−0.014 (4)	0.005 (4)
C36	0.068 (5)	0.062 (4)	0.103 (4)	−0.028 (4)	−0.020 (4)	0.003 (4)
N12A	0.081 (4)	0.073 (5)	0.122 (4)	−0.016 (4)	−0.009 (3)	0.023 (4)
C33A	0.083 (5)	0.081 (5)	0.122 (6)	−0.025 (4)	−0.007 (4)	0.021 (4)
C34A	0.072 (6)	0.066 (4)	0.112 (6)	−0.040 (4)	−0.015 (4)	0.020 (4)
C35A	0.070 (6)	0.060 (4)	0.107 (5)	−0.045 (4)	−0.016 (4)	0.007 (4)
C36A	0.064 (5)	0.060 (4)	0.102 (4)	−0.032 (3)	−0.020 (4)	−0.001 (4)

Geometric parameters (Å, º) top

S1—C1	1.759 (3)	N9—C20	1.332 (4)
S1—C4	1.770 (4)	N9—C21	1.338 (4)
S2—C2	1.746 (3)	N10—C22	1.313 (4)
S2—C9	1.783 (4)	N10—C23	1.326 (5)
S3—C3	1.754 (4)	C22—C26	1.377 (4)
S3—C14	1.774 (4)	C23—C24	1.359 (5)
N1—C1	1.333 (4)	C23—H23	0.9300
N1—C3	1.347 (4)	C24—C25	1.340 (5)
N2—C1	1.319 (4)	C24—H24	0.9300
N2—C2	1.355 (4)	C25—C26	1.373 (5)
N3—C2	1.325 (4)	C25—H25	0.9300
N3—C3	1.327 (4)	C26—H26	0.9300
N4—C4	1.327 (4)	C27—N11	1.340 (5)
N4—C5	1.347 (4)	C27—N11A	1.340 (7)
N5—C9	1.328 (4)	C27—C31A	1.364 (7)
N5—C10	1.346 (5)	C27—C31	1.366 (5)
N6—C14	1.319 (4)	N11—C28	1.344 (5)
N6—C15	1.348 (5)	C28—C29	1.358 (5)
C4—C8	1.376 (4)	C28—H28	0.9300
C5—C6	1.375 (5)	C29—C30	1.399 (6)
C5—H5	0.9300	C29—H29	0.9300
C6—C7	1.364 (4)	C30—C31	1.376 (5)
C6—H6	0.9300	C30—H30	0.9300
C7—C8	1.372 (5)	C31—H31	0.9300
C7—H7	0.9300	N11A—C28A	1.351 (7)
C8—H8	0.9300	C28A—C29A	1.360 (8)
C9—C13	1.340 (5)	C28A—H28A	0.9300
C10—C11	1.360 (5)	C29A—C30A	1.399 (8)
C10—H10	0.9300	C29A—H29A	0.9300
C11—C12	1.351 (5)	C30A—C31A	1.380 (7)
C11—H11	0.9300	C30A—H30A	0.9300
C12—C13	1.363 (5)	C31A—H31A	0.9300
C12—H12	0.9300	C32—N12	1.342 (6)
C13—H13	0.9300	C32—N12A	1.342 (6)
C14—C18	1.365 (5)	C32—C36	1.350 (6)
C15—C16	1.362 (6)	C32—C36A	1.367 (6)
C15—H15	0.9300	N12—C33	1.352 (6)
C16—C17	1.339 (6)	C33—C34	1.365 (7)
C16—H16	0.9300	C33—H33	0.9300
C17—C18	1.386 (5)	C34—C35	1.395 (7)
C17—H17	0.9300	C34—H34	0.9300
C18—H18	0.9300	C35—C36	1.381 (6)
S4—C19	1.751 (3)	C35—H35	0.9300
S4—C22	1.770 (4)	C36—H36	0.9300
S5—C20	1.747 (3)	N12A—C33A	1.347 (7)
S5—C27	1.772 (4)	C33A—C34A	1.356 (7)
S6—C21	1.746 (3)	C33A—H33A	0.9300
S6—C32	1.762 (4)	C34A—C35A	1.393 (7)
N7—C21	1.321 (4)	C34A—H34A	0.9300
N7—C19	1.327 (4)	C35A—C36A	1.379 (6)
N8—C19	1.330 (4)	C35A—H35A	0.9300
N8—C20	1.342 (4)	C36A—H36A	0.9300

C1—S1—C4	110.37 (19)	N10—C22—C26	123.1 (4)
C2—S2—C9	101.53 (18)	N10—C22—S4	112.0 (4)
C3—S3—C14	101.14 (19)	C26—C22—S4	124.9 (4)
C1—N1—C3	113.0 (3)	N10—C23—C24	124.8 (5)
C1—N2—C2	112.9 (3)	N10—C23—H23	117.6
C2—N3—C3	112.8 (3)	C24—C23—H23	117.6
C4—N4—C5	117.1 (3)	C25—C24—C23	119.4 (5)
C9—N5—C10	115.5 (4)	C25—C24—H24	120.3
C14—N6—C15	116.2 (4)	C23—C24—H24	120.3
N2—C1—N1	127.0 (3)	C24—C25—C26	117.4 (5)
N2—C1—S1	122.9 (3)	C24—C25—H25	121.3
N1—C1—S1	110.0 (3)	C26—C25—H25	121.3
N3—C2—N2	127.2 (3)	C25—C26—C22	119.7 (4)
N3—C2—S2	120.7 (3)	C25—C26—H26	120.1
N2—C2—S2	112.1 (3)	C22—C26—H26	120.1
N3—C3—N1	127.0 (3)	N11A—C27—C31A	124.5 (6)
N3—C3—S3	119.7 (3)	N11—C27—C31	124.8 (4)
N1—C3—S3	113.3 (3)	N11—C27—S5	112.5 (3)
N4—C4—C8	122.3 (3)	N11A—C27—S5	116.2 (5)
N4—C4—S1	107.8 (3)	C31A—C27—S5	119.3 (5)
C8—C4—S1	129.9 (3)	C31—C27—S5	122.4 (4)
N4—C5—C6	123.9 (4)	C27—N11—C28	114.7 (4)
N4—C5—H5	118.0	N11—C28—C29	125.5 (5)
C6—C5—H5	118.0	N11—C28—H28	117.3
C7—C6—C5	117.8 (4)	C29—C28—H28	117.3
C7—C6—H6	121.1	C28—C29—C30	117.8 (5)
C5—C6—H6	121.1	C28—C29—H29	121.1
C6—C7—C8	119.2 (4)	C30—C29—H29	121.1
C6—C7—H7	120.4	C31—C30—C29	118.2 (5)
C8—C7—H7	120.4	C31—C30—H30	120.9
C7—C8—C4	119.7 (4)	C29—C30—H30	120.9
C7—C8—H8	120.2	C27—C31—C30	118.7 (5)
C4—C8—H8	120.2	C27—C31—H31	120.7
N5—C9—C13	124.2 (4)	C30—C31—H31	120.7
N5—C9—S2	115.0 (4)	C27—N11A—C28A	115.1 (6)
C13—C9—S2	120.8 (4)	N11A—C28A—C29A	124.9 (7)
N5—C10—C11	123.3 (5)	N11A—C28A—H28A	117.6
N5—C10—H10	118.3	C29A—C28A—H28A	117.6
C11—C10—H10	118.3	C28A—C29A—C30A	116.9 (7)
C12—C11—C10	118.9 (5)	C28A—C29A—H29A	121.5
C12—C11—H11	120.6	C30A—C29A—H29A	121.5
C10—C11—H11	120.6	C31A—C30A—C29A	117.9 (7)
C11—C12—C13	118.8 (5)	C31A—C30A—H30A	121.0
C11—C12—H12	120.6	C29A—C30A—H30A	121.0
C13—C12—H12	120.6	C27—C31A—C30A	118.4 (6)
C9—C13—C12	119.2 (4)	C27—C31A—H31A	120.8
C9—C13—H13	120.4	C30A—C31A—H31A	120.8
C12—C13—H13	120.4	N12—C32—C36	126.3 (5)
N6—C14—C18	123.6 (4)	N12A—C32—C36A	123.4 (5)
N6—C14—S3	115.1 (4)	N12—C32—S6	105.2 (5)
C18—C14—S3	121.2 (4)	N12A—C32—S6	123.0 (6)
N6—C15—C16	123.4 (5)	C36—C32—S6	127.5 (5)
N6—C15—H15	118.3	C36A—C32—S6	113.6 (5)
C16—C15—H15	118.3	C32—N12—C33	113.0 (5)
C17—C16—C15	119.6 (6)	N12—C33—C34	125.4 (6)
C17—C16—H16	120.2	N12—C33—H33	117.3
C15—C16—H16	120.2	C34—C33—H33	117.3
C16—C17—C18	118.4 (5)	C33—C34—C35	118.2 (6)
C16—C17—H17	120.8	C33—C34—H34	120.9
C18—C17—H17	120.8	C35—C34—H34	120.9
C14—C18—C17	118.8 (5)	C36—C35—C34	117.7 (6)
C14—C18—H18	120.6	C36—C35—H35	121.1
C17—C18—H18	120.6	C34—C35—H35	121.1
C19—S4—C22	106.85 (19)	C32—C36—C35	118.4 (6)
C20—S5—C27	102.74 (18)	C32—C36—H36	120.8
C21—S6—C32	104.71 (19)	C35—C36—H36	120.8
C21—N7—C19	113.6 (3)	C32—N12A—C33A	114.9 (6)
C19—N8—C20	113.2 (3)	N12A—C33A—C34A	125.9 (6)
C20—N9—C21	112.4 (3)	N12A—C33A—H33A	117.1
C22—N10—C23	115.6 (4)	C34A—C33A—H33A	117.1
N7—C19—N8	126.6 (3)	C33A—C34A—C35A	117.2 (6)
N7—C19—S4	112.1 (3)	C33A—C34A—H34A	121.4
N8—C19—S4	121.3 (3)	C35A—C34A—H34A	121.4
N9—C20—N8	126.9 (3)	C36A—C35A—C34A	118.6 (6)
N9—C20—S5	121.8 (3)	C36A—C35A—H35A	120.7
N8—C20—S5	111.4 (3)	C34A—C35A—H35A	120.7
N7—C21—N9	127.4 (3)	C32—C36A—C35A	119.2 (6)
N7—C21—S6	112.5 (3)	C32—C36A—H36A	120.4
N9—C21—S6	120.1 (3)	C35A—C36A—H36A	120.4

C2—N2—C1—N1	−2.7 (5)	C23—N10—C22—C26	−1.1 (6)
C2—N2—C1—S1	177.0 (2)	C23—N10—C22—S4	−178.4 (3)
C3—N1—C1—N2	2.5 (5)	C19—S4—C22—N10	−136.8 (3)
C3—N1—C1—S1	−177.3 (2)	C19—S4—C22—C26	45.9 (4)
C4—S1—C1—N2	−10.8 (3)	C22—N10—C23—C24	−1.4 (7)
C4—S1—C1—N1	168.9 (2)	N10—C23—C24—C25	2.6 (9)
C3—N3—C2—N2	0.0 (5)	C23—C24—C25—C26	−1.2 (7)
C3—N3—C2—S2	179.8 (2)	C24—C25—C26—C22	−1.1 (7)
C1—N2—C2—N3	1.3 (5)	N10—C22—C26—C25	2.4 (6)
C1—N2—C2—S2	−178.5 (2)	S4—C22—C26—C25	179.3 (3)
C9—S2—C2—N3	3.2 (3)	C20—S5—C27—N11	−120.6 (5)
C9—S2—C2—N2	−176.9 (3)	C20—S5—C27—N11A	−88.5 (9)
C2—N3—C3—N1	−0.2 (5)	C20—S5—C27—C31A	91.0 (10)
C2—N3—C3—S3	−179.0 (2)	C20—S5—C27—C31	64.8 (6)
C1—N1—C3—N3	−0.8 (5)	N11A—C27—N11—C28	77.9 (12)
C1—N1—C3—S3	178.0 (2)	C31A—C27—N11—C28	−30.1 (10)
C14—S3—C3—N3	5.0 (4)	C31—C27—N11—C28	−3.7 (8)
C14—S3—C3—N1	−174.0 (3)	S5—C27—N11—C28	−178.2 (4)
C5—N4—C4—C8	−1.0 (5)	C27—N11—C28—C29	3.6 (9)
C5—N4—C4—S1	177.7 (3)	N11—C28—C29—C30	−4.2 (11)
C1—S1—C4—N4	−175.9 (2)	C28—C29—C30—C31	4.7 (10)
C1—S1—C4—C8	2.7 (4)	N11—C27—C31—C30	4.7 (8)
C4—N4—C5—C6	−0.1 (6)	N11A—C27—C31—C30	−28.1 (10)
N4—C5—C6—C7	0.9 (6)	C31A—C27—C31—C30	89.5 (17)
C5—C6—C7—C8	−0.7 (6)	S5—C27—C31—C30	178.6 (4)
C6—C7—C8—C4	−0.4 (6)	C29—C30—C31—C27	−4.9 (9)
N4—C4—C8—C7	1.3 (6)	N11—C27—N11A—C28A	−94.3 (16)
S1—C4—C8—C7	−177.2 (3)	C31A—C27—N11A—C28A	−3.5 (18)
C10—N5—C9—C13	0.2 (7)	C31—C27—N11A—C28A	21.0 (15)
C10—N5—C9—S2	−177.8 (3)	S5—C27—N11A—C28A	176.0 (9)
C2—S2—C9—N5	−105.0 (3)	C27—N11A—C28A—C29A	−2 (2)
C2—S2—C9—C13	76.9 (4)	N11A—C28A—C29A—C30A	13 (3)
C9—N5—C10—C11	0.4 (7)	C28A—C29A—C30A—C31A	−18 (3)
N5—C10—C11—C12	−0.7 (8)	N11—C27—C31A—C30A	32.1 (18)
C10—C11—C12—C13	0.4 (7)	N11A—C27—C31A—C30A	−2 (2)
N5—C9—C13—C12	−0.5 (7)	C31—C27—C31A—C30A	−77.3 (18)
S2—C9—C13—C12	177.4 (3)	S5—C27—C31A—C30A	178.2 (11)
C11—C12—C13—C9	0.2 (7)	C29A—C30A—C31A—C27	13 (3)
C15—N6—C14—C18	0.6 (6)	C21—S6—C32—N12	114.8 (8)
C15—N6—C14—S3	−177.9 (3)	C21—S6—C32—N12A	107.5 (11)
C3—S3—C14—N6	−102.7 (3)	C21—S6—C32—C36	−76.2 (13)
C3—S3—C14—C18	78.7 (4)	C21—S6—C32—C36A	−70.0 (11)
C14—N6—C15—C16	−1.0 (7)	N12A—C32—N12—C33	−19 (4)
N6—C15—C16—C17	0.9 (8)	C36—C32—N12—C33	11 (2)
C15—C16—C17—C18	−0.4 (8)	C36A—C32—N12—C33	7 (3)
N6—C14—C18—C17	−0.2 (7)	S6—C32—N12—C33	−179.7 (11)
S3—C14—C18—C17	178.2 (3)	C32—N12—C33—C34	−6 (2)
C16—C17—C18—C14	0.1 (7)	N12—C33—C34—C35	−2.2 (18)
C21—N7—C19—N8	−0.6 (5)	C33—C34—C35—C36	5.7 (18)
C21—N7—C19—S4	179.0 (3)	N12—C32—C36—C35	−8 (2)
C20—N8—C19—N7	−1.0 (5)	N12A—C32—C36—C35	2 (2)
C20—N8—C19—S4	179.4 (3)	C36A—C32—C36—C35	163 (9)
C22—S4—C19—N7	172.7 (3)	S6—C32—C36—C35	−174.8 (9)
C22—S4—C19—N8	−7.6 (4)	C34—C35—C36—C32	−1 (2)
C21—N9—C20—N8	−0.2 (5)	N12—C32—N12A—C33A	150 (6)
C21—N9—C20—S5	179.6 (2)	C36—C32—N12A—C33A	−5 (2)
C19—N8—C20—N9	1.5 (5)	C36A—C32—N12A—C33A	−11 (2)
C19—N8—C20—S5	−178.4 (3)	S6—C32—N12A—C33A	171.9 (11)
C27—S5—C20—N9	−3.3 (3)	C32—N12A—C33A—C34A	8 (3)
C27—S5—C20—N8	176.6 (3)	N12A—C33A—C34A—C35A	−2 (2)
C19—N7—C21—N9	2.2 (5)	C33A—C34A—C35A—C36A	−0.8 (17)
C19—N7—C21—S6	−178.9 (3)	N12—C32—C36A—C35A	−1 (3)
C20—N9—C21—N7	−1.8 (5)	N12A—C32—C36A—C35A	8 (3)
C20—N9—C21—S6	179.4 (2)	C36—C32—C36A—C35A	−13 (6)
C32—S6—C21—N7	168.8 (3)	S6—C32—C36A—C35A	−174.0 (12)
C32—S6—C21—N9	−12.2 (3)	C34A—C35A—C36A—C32	−2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···N6ⁱ	0.93	2.63	3.457 (6)	149
C17—H17···N10	0.93	2.84	3.644 (6)	145
C11—H11···S4	0.93	3.23	4.002 (5)	142
C16—H16···S4	0.93	3.45	4.259 (5)	147
C24—H24···S1ⁱ	0.93	2.98	3.816 (4)	150

Symmetry code: (i) x+1/2, −y+3/2, −z+2.

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2,4,6-Tris(pyridin-2-ylsulfan­yl)-1,3,5-triazine

Supporting information

Key indicators

checkCIF/PLATON results

2,4,6-Tris(pyridin-2-ylsulfanyl)-1,3,5-triazine