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In the title compound, C
17H
17N
5O
2S, the dihedral angles between the plane of the 4,6-dimethyl-2-mercaptopyrimidine group and the plane of the triazole and
p-methoxyphenylcarbonyl groups are 79.64 (2) and 0.44 (2)°, respectively. There are weak C—H
O and C—H
N intermolecular interactions between the molecules in the crystal lattice.
Supporting information
CCDC reference: 226959
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.125
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C16
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PLEASE PROVIDE; cell refinement: PLEASE PROVIDE; data reduction: PLEASE PROVIDE; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: WinGX (Farrugia, 1999).
Crystal data top
C17H17N5O2S | F(000) = 744 |
Mr = 355.42 | Dx = 1.346 Mg m−3 |
Monoclinic, P21/c | Melting point = 420–421 K |
Hall symbol: -P 2y bc | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0158 (16) Å | Cell parameters from 20 reflections |
b = 12.462 (3) Å | θ = 2–11° |
c = 17.824 (4) Å | µ = 0.21 mm−1 |
β = 99.89 (3)° | T = 293 K |
V = 1754.0 (7) Å3 | Pillar, yellow |
Z = 4 | 0.25 × 0.20 × 0.15 mm |
Data collection top
Oxford Instruments point-detector diffractometer | Rint = 0.031 |
Radiation source: fine-focus sealed tube | θmax = 25.9°, θmin = 2.8° |
Graphite monochromator | h = −9→9 |
θ/2θ scans | k = 0→15 |
5553 measured reflections | l = −21→21 |
3257 independent reflections | 3 standard reflections every 100 reflections |
2334 reflections with I > 2σ(I) | intensity decay: 0.9% |
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) = 0.125 | w = 1/[σ2(Fo2) + (0.0696P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3257 reflections | Δρmax = 0.25 e Å−3 |
227 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0062 (12) |
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 | Uiso*/Ueq | |
S1 | 0.80796 (8) | 0.19144 (5) | 0.43339 (3) | 0.0548 (2) | |
O1 | 0.8926 (2) | 0.83294 (15) | 0.33798 (10) | 0.0689 (5) | |
O2 | 0.9401 (2) | 0.32648 (14) | 0.33395 (10) | 0.0612 (5) | |
N1 | 0.5955 (2) | 0.36351 (14) | 0.41242 (9) | 0.0405 (4) | |
N2 | 0.5153 (2) | 0.36244 (17) | 0.33822 (10) | 0.0520 (5) | |
N3 | 0.3323 (3) | 0.40295 (18) | 0.41768 (11) | 0.0592 (6) | |
N4 | 0.7316 (3) | 0.05129 (16) | 0.52949 (12) | 0.0593 (6) | |
N5 | 0.7046 (2) | 0.23472 (17) | 0.56621 (10) | 0.0516 (5) | |
C1 | 0.8356 (4) | 0.9060 (2) | 0.39000 (17) | 0.0750 (8) | |
H1A | 0.8471 | 0.9782 | 0.3730 | 0.112* | |
H1B | 0.9025 | 0.8969 | 0.4397 | 0.112* | |
H1C | 0.7189 | 0.8918 | 0.3923 | 0.112* | |
C2 | 0.8865 (3) | 0.7257 (2) | 0.35252 (13) | 0.0490 (6) | |
C3 | 0.9316 (3) | 0.6590 (2) | 0.29629 (13) | 0.0544 (6) | |
H3B | 0.9639 | 0.6886 | 0.2531 | 0.065* | |
C4 | 0.9282 (3) | 0.5500 (2) | 0.30498 (12) | 0.0489 (6) | |
H4B | 0.9591 | 0.5061 | 0.2675 | 0.059* | |
C5 | 0.8792 (2) | 0.50340 (18) | 0.36905 (11) | 0.0403 (5) | |
C6 | 0.8388 (3) | 0.57107 (19) | 0.42514 (12) | 0.0450 (6) | |
H6A | 0.8082 | 0.5415 | 0.4687 | 0.054* | |
C7 | 0.8430 (3) | 0.68131 (19) | 0.41760 (13) | 0.0483 (6) | |
H7A | 0.8167 | 0.7254 | 0.4560 | 0.058* | |
C8 | 0.8733 (3) | 0.38544 (19) | 0.37435 (12) | 0.0432 (5) | |
C9 | 0.7741 (3) | 0.33553 (18) | 0.43204 (12) | 0.0410 (5) | |
H9A | 0.8185 | 0.3643 | 0.4827 | 0.049* | |
C10 | 0.4833 (3) | 0.38667 (19) | 0.45716 (12) | 0.0484 (6) | |
H10A | 0.5091 | 0.3907 | 0.5100 | 0.058* | |
C11 | 0.3598 (3) | 0.3868 (2) | 0.34567 (13) | 0.0570 (7) | |
H11A | 0.2732 | 0.3926 | 0.3038 | 0.068* | |
C12 | 0.7391 (3) | 0.1573 (2) | 0.51982 (13) | 0.0501 (6) | |
C13 | 0.6580 (3) | 0.2019 (2) | 0.63200 (13) | 0.0549 (7) | |
C14 | 0.6488 (3) | 0.0938 (2) | 0.64806 (15) | 0.0638 (8) | |
H14A | 0.6179 | 0.0712 | 0.6935 | 0.077* | |
C15 | 0.6863 (3) | 0.0196 (2) | 0.59560 (16) | 0.0631 (7) | |
C16 | 0.6174 (4) | 0.2878 (2) | 0.68452 (13) | 0.0706 (8) | |
H16A | 0.6317 | 0.3569 | 0.6626 | 0.106* | |
H16B | 0.6922 | 0.2819 | 0.7326 | 0.106* | |
H16C | 0.5024 | 0.2800 | 0.6921 | 0.106* | |
C17 | 0.6770 (4) | −0.0997 (2) | 0.60760 (19) | 0.0898 (10) | |
H17A | 0.7086 | −0.1365 | 0.5649 | 0.135* | |
H17B | 0.5635 | −0.1192 | 0.6124 | 0.135* | |
H17C | 0.7531 | −0.1194 | 0.6532 | 0.135* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0691 (4) | 0.0399 (4) | 0.0593 (4) | 0.0028 (3) | 0.0221 (3) | 0.0019 (3) |
O1 | 0.0878 (14) | 0.0442 (11) | 0.0765 (12) | −0.0021 (9) | 0.0194 (10) | 0.0085 (9) |
O2 | 0.0745 (12) | 0.0512 (11) | 0.0680 (11) | 0.0010 (9) | 0.0405 (9) | −0.0094 (9) |
N1 | 0.0452 (10) | 0.0407 (11) | 0.0388 (9) | −0.0024 (8) | 0.0162 (8) | −0.0020 (8) |
N2 | 0.0537 (12) | 0.0650 (15) | 0.0385 (10) | 0.0000 (10) | 0.0116 (9) | −0.0043 (9) |
N3 | 0.0546 (12) | 0.0718 (16) | 0.0545 (12) | 0.0131 (11) | 0.0188 (10) | 0.0013 (10) |
N4 | 0.0605 (13) | 0.0459 (13) | 0.0692 (13) | −0.0055 (10) | 0.0043 (10) | 0.0115 (11) |
N5 | 0.0549 (12) | 0.0542 (13) | 0.0465 (11) | −0.0002 (10) | 0.0109 (9) | 0.0103 (10) |
C1 | 0.0748 (19) | 0.0449 (17) | 0.105 (2) | 0.0044 (14) | 0.0153 (17) | −0.0044 (16) |
C2 | 0.0469 (13) | 0.0422 (14) | 0.0582 (14) | −0.0048 (11) | 0.0095 (11) | 0.0039 (12) |
C3 | 0.0659 (16) | 0.0536 (16) | 0.0474 (13) | −0.0108 (12) | 0.0202 (11) | 0.0048 (11) |
C4 | 0.0543 (13) | 0.0505 (16) | 0.0462 (12) | −0.0061 (11) | 0.0205 (10) | −0.0040 (11) |
C5 | 0.0413 (12) | 0.0434 (14) | 0.0388 (11) | −0.0035 (10) | 0.0145 (9) | −0.0033 (9) |
C6 | 0.0466 (13) | 0.0479 (14) | 0.0439 (12) | −0.0021 (11) | 0.0171 (10) | −0.0001 (10) |
C7 | 0.0498 (13) | 0.0446 (15) | 0.0528 (13) | −0.0036 (11) | 0.0151 (10) | −0.0058 (11) |
C8 | 0.0448 (12) | 0.0457 (14) | 0.0417 (11) | −0.0021 (11) | 0.0147 (10) | −0.0025 (10) |
C9 | 0.0434 (12) | 0.0393 (13) | 0.0421 (12) | −0.0019 (9) | 0.0123 (9) | −0.0012 (9) |
C10 | 0.0585 (15) | 0.0500 (15) | 0.0416 (12) | 0.0056 (12) | 0.0221 (11) | −0.0018 (10) |
C11 | 0.0513 (14) | 0.0706 (19) | 0.0490 (14) | 0.0022 (13) | 0.0088 (11) | −0.0041 (12) |
C12 | 0.0492 (14) | 0.0464 (15) | 0.0535 (14) | −0.0021 (11) | 0.0056 (11) | 0.0108 (12) |
C13 | 0.0456 (13) | 0.0689 (19) | 0.0491 (13) | −0.0015 (12) | 0.0047 (11) | 0.0142 (13) |
C14 | 0.0545 (15) | 0.073 (2) | 0.0632 (16) | −0.0058 (14) | 0.0088 (13) | 0.0274 (15) |
C15 | 0.0520 (15) | 0.0579 (18) | 0.0747 (17) | −0.0101 (13) | −0.0026 (13) | 0.0263 (15) |
C16 | 0.0721 (19) | 0.090 (2) | 0.0524 (15) | 0.0048 (16) | 0.0185 (13) | 0.0126 (15) |
C17 | 0.099 (2) | 0.061 (2) | 0.104 (2) | −0.0195 (17) | 0.0005 (19) | 0.0290 (17) |
Geometric parameters (Å, º) top
S1—C12 | 1.775 (3) | C4—C5 | 1.396 (3) |
S1—C9 | 1.816 (2) | C4—H4B | 0.9300 |
O1—C2 | 1.364 (3) | C5—C6 | 1.388 (3) |
O1—C1 | 1.429 (3) | C5—C8 | 1.474 (3) |
O2—C8 | 1.215 (3) | C6—C7 | 1.381 (3) |
N1—C10 | 1.332 (3) | C6—H6A | 0.9300 |
N1—N2 | 1.368 (2) | C7—H7A | 0.9300 |
N1—C9 | 1.456 (3) | C8—C9 | 1.536 (3) |
N2—C11 | 1.312 (3) | C9—H9A | 0.9800 |
N3—C10 | 1.307 (3) | C10—H10A | 0.9300 |
N3—C11 | 1.354 (3) | C11—H11A | 0.9300 |
N4—C12 | 1.335 (3) | C13—C14 | 1.381 (4) |
N4—C15 | 1.350 (3) | C13—C16 | 1.494 (3) |
N5—C12 | 1.331 (3) | C14—C15 | 1.384 (4) |
N5—C13 | 1.354 (3) | C14—H14A | 0.9300 |
C1—H1A | 0.9600 | C15—C17 | 1.506 (4) |
C1—H1B | 0.9600 | C16—H16A | 0.9600 |
C1—H1C | 0.9600 | C16—H16B | 0.9600 |
C2—C7 | 1.383 (3) | C16—H16C | 0.9600 |
C2—C3 | 1.396 (3) | C17—H17A | 0.9600 |
C3—C4 | 1.368 (3) | C17—H17B | 0.9600 |
C3—H3B | 0.9300 | C17—H17C | 0.9600 |
| | | |
C12—S1—C9 | 100.40 (11) | N1—C9—C8 | 110.07 (17) |
C2—O1—C1 | 118.3 (2) | N1—C9—S1 | 112.26 (14) |
C10—N1—N2 | 109.10 (18) | C8—C9—S1 | 108.41 (15) |
C10—N1—C9 | 130.16 (17) | N1—C9—H9A | 108.7 |
N2—N1—C9 | 120.62 (17) | C8—C9—H9A | 108.7 |
C11—N2—N1 | 101.36 (18) | S1—C9—H9A | 108.7 |
C10—N3—C11 | 101.6 (2) | N3—C10—N1 | 111.67 (19) |
C12—N4—C15 | 115.3 (2) | N3—C10—H10A | 124.2 |
C12—N5—C13 | 115.9 (2) | N1—C10—H10A | 124.2 |
O1—C1—H1A | 109.5 | N2—C11—N3 | 116.3 (2) |
O1—C1—H1B | 109.5 | N2—C11—H11A | 121.9 |
H1A—C1—H1B | 109.5 | N3—C11—H11A | 121.9 |
O1—C1—H1C | 109.5 | N5—C12—N4 | 128.2 (2) |
H1A—C1—H1C | 109.5 | N5—C12—S1 | 119.62 (18) |
H1B—C1—H1C | 109.5 | N4—C12—S1 | 112.2 (2) |
O1—C2—C7 | 125.0 (2) | N5—C13—C14 | 120.5 (3) |
O1—C2—C3 | 115.1 (2) | N5—C13—C16 | 116.6 (2) |
C7—C2—C3 | 119.9 (2) | C14—C13—C16 | 122.9 (2) |
C4—C3—C2 | 119.8 (2) | C13—C14—C15 | 119.1 (2) |
C4—C3—H3B | 120.1 | C13—C14—H14A | 120.5 |
C2—C3—H3B | 120.1 | C15—C14—H14A | 120.5 |
C3—C4—C5 | 121.3 (2) | N4—C15—C14 | 121.1 (2) |
C3—C4—H4B | 119.3 | N4—C15—C17 | 116.1 (3) |
C5—C4—H4B | 119.3 | C14—C15—C17 | 122.8 (3) |
C6—C5—C4 | 118.0 (2) | C13—C16—H16A | 109.5 |
C6—C5—C8 | 123.1 (2) | C13—C16—H16B | 109.5 |
C4—C5—C8 | 118.9 (2) | H16A—C16—H16B | 109.5 |
C7—C6—C5 | 121.4 (2) | C13—C16—H16C | 109.5 |
C7—C6—H6A | 119.3 | H16A—C16—H16C | 109.5 |
C5—C6—H6A | 119.3 | H16B—C16—H16C | 109.5 |
C6—C7—C2 | 119.5 (2) | C15—C17—H17A | 109.5 |
C6—C7—H7A | 120.2 | C15—C17—H17B | 109.5 |
C2—C7—H7A | 120.2 | H17A—C17—H17B | 109.5 |
O2—C8—C5 | 122.9 (2) | C15—C17—H17C | 109.5 |
O2—C8—C9 | 118.9 (2) | H17A—C17—H17C | 109.5 |
C5—C8—C9 | 118.21 (19) | H17B—C17—H17C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3B···O2i | 0.93 | 2.52 | 3.409 (2) | 159 |
C6—H6A···N3ii | 0.93 | 2.57 | 3.340 (3) | 139 |
C9—H9A···N5 | 0.98 | 2.47 | 2.840 (3) | 102 |
C10—H10A···N5 | 0.93 | 2.58 | 3.054 (3) | 111 |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z+1. |
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