In the crystal structure of the title compound, C
16H
15N
3OS, intermolecular N—H
S hydrogen bonds link the molecules together as characteristic dimers, which are further stabilized by weak intermolecular benzene-ring π–π interactions along the
a-axis direction.
Supporting information
CCDC reference: 613847
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.114
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 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: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
3-(4-Methylphenoxymethyl)-4-phenyl-1
H-1,2,4triazole-5(4
H)-thione
top
Crystal data top
C16H15N3OS | Z = 2 |
Mr = 297.37 | F(000) = 312 |
Triclinic, P1 | Dx = 1.293 Mg m−3 |
a = 7.182 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.846 (4) Å | Cell parameters from 3183 reflections |
c = 11.644 (5) Å | θ = 0.0–0.0° |
α = 71.283 (7)° | µ = 0.21 mm−1 |
β = 78.783 (7)° | T = 293 K |
γ = 89.372 (7)° | Block, colorless |
V = 763.8 (6) Å3 | 0.52 × 0.47 × 0.25 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2971 independent reflections |
Radiation source: fine-focus sealed tube | 2302 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
φ and ω scans | θmax = 26.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −8→8 |
Tmin = 0.897, Tmax = 0.949 | k = −12→12 |
5977 measured reflections | l = −13→14 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0592P)2 + 0.1617P] where P = (Fo2 + 2Fc2)/3 |
2971 reflections | (Δ/σ)max < 0.001 |
195 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
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 | |
C1 | 0.2818 (2) | 0.96740 (18) | 0.38206 (15) | 0.0470 (4) | |
C2 | 0.5206 (2) | 0.83767 (19) | 0.44447 (15) | 0.0497 (4) | |
C3 | 0.7094 (3) | 0.7750 (2) | 0.43999 (17) | 0.0545 (4) | |
H3A | 0.8082 | 0.8475 | 0.3891 | 0.065* | |
H3B | 0.7361 | 0.7372 | 0.5226 | 0.065* | |
C4 | 0.8744 (2) | 0.61585 (18) | 0.34325 (17) | 0.0521 (4) | |
C5 | 0.8686 (3) | 0.5339 (3) | 0.2679 (2) | 0.0789 (7) | |
H5 | 0.7532 | 0.5132 | 0.2505 | 0.095* | |
C6 | 1.0333 (3) | 0.4826 (3) | 0.2180 (2) | 0.0809 (7) | |
H6 | 1.0269 | 0.4280 | 0.1667 | 0.097* | |
C7 | 1.2059 (3) | 0.5097 (2) | 0.24186 (19) | 0.0616 (5) | |
C8 | 1.2079 (3) | 0.5879 (2) | 0.32009 (19) | 0.0615 (5) | |
H8 | 1.3226 | 0.6053 | 0.3401 | 0.074* | |
C9 | 1.0447 (3) | 0.6417 (2) | 0.37032 (17) | 0.0559 (4) | |
H9 | 1.0509 | 0.6954 | 0.4224 | 0.067* | |
C10 | 1.3856 (4) | 0.4557 (3) | 0.1839 (3) | 0.0922 (8) | |
H10A | 1.4609 | 0.5349 | 0.1215 | 0.138* | |
H10B | 1.3533 | 0.3873 | 0.1469 | 0.138* | |
H10C | 1.4568 | 0.4105 | 0.2464 | 0.138* | |
C11 | 0.5756 (2) | 0.9863 (2) | 0.21883 (14) | 0.0486 (4) | |
C12 | 0.6092 (3) | 0.8974 (3) | 0.14753 (18) | 0.0654 (5) | |
H12 | 0.5589 | 0.8031 | 0.1776 | 0.078* | |
C13 | 0.7205 (3) | 0.9529 (3) | 0.02928 (19) | 0.0821 (7) | |
H13 | 0.7461 | 0.8948 | −0.0204 | 0.099* | |
C14 | 0.7919 (3) | 1.0905 (3) | −0.01427 (19) | 0.0862 (8) | |
H14 | 0.8646 | 1.1266 | −0.0940 | 0.103* | |
C15 | 0.7579 (3) | 1.1772 (3) | 0.0582 (2) | 0.0841 (7) | |
H15 | 0.8085 | 1.2714 | 0.0278 | 0.101* | |
C16 | 0.6481 (3) | 1.1246 (2) | 0.17689 (18) | 0.0658 (5) | |
H16 | 0.6245 | 1.1827 | 0.2267 | 0.079* | |
N1 | 0.46203 (19) | 0.93033 (15) | 0.34325 (12) | 0.0470 (3) | |
N2 | 0.2445 (2) | 0.89431 (17) | 0.50347 (13) | 0.0523 (4) | |
N3 | 0.3903 (2) | 0.81319 (17) | 0.54406 (13) | 0.0560 (4) | |
O1 | 0.70311 (17) | 0.66276 (14) | 0.38825 (14) | 0.0641 (4) | |
S1 | 0.14154 (7) | 1.07616 (6) | 0.29890 (4) | 0.06245 (19) | |
H2 | 0.140 (3) | 0.898 (2) | 0.555 (2) | 0.068 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0428 (9) | 0.0565 (10) | 0.0391 (8) | 0.0037 (7) | 0.0038 (7) | −0.0192 (7) |
C2 | 0.0500 (10) | 0.0574 (10) | 0.0375 (8) | 0.0060 (8) | −0.0011 (7) | −0.0144 (7) |
C3 | 0.0509 (10) | 0.0642 (11) | 0.0469 (10) | 0.0108 (8) | −0.0071 (8) | −0.0180 (8) |
C4 | 0.0464 (10) | 0.0498 (10) | 0.0561 (10) | 0.0093 (8) | −0.0085 (8) | −0.0130 (8) |
C5 | 0.0581 (13) | 0.0883 (16) | 0.1131 (19) | 0.0164 (11) | −0.0301 (13) | −0.0570 (15) |
C6 | 0.0760 (15) | 0.0875 (16) | 0.0997 (18) | 0.0200 (12) | −0.0213 (13) | −0.0567 (15) |
C7 | 0.0544 (11) | 0.0576 (11) | 0.0654 (12) | 0.0084 (9) | −0.0027 (9) | −0.0154 (9) |
C8 | 0.0461 (10) | 0.0623 (11) | 0.0696 (12) | 0.0045 (8) | −0.0090 (9) | −0.0143 (10) |
C9 | 0.0531 (11) | 0.0581 (11) | 0.0557 (11) | 0.0057 (8) | −0.0095 (8) | −0.0184 (9) |
C10 | 0.0713 (15) | 0.0929 (17) | 0.108 (2) | 0.0181 (13) | 0.0045 (14) | −0.0397 (15) |
C11 | 0.0379 (8) | 0.0674 (11) | 0.0322 (8) | 0.0113 (8) | 0.0025 (6) | −0.0110 (8) |
C12 | 0.0615 (12) | 0.0878 (14) | 0.0464 (10) | 0.0169 (10) | −0.0013 (9) | −0.0272 (10) |
C13 | 0.0700 (14) | 0.132 (2) | 0.0420 (11) | 0.0332 (15) | 0.0003 (10) | −0.0334 (13) |
C14 | 0.0507 (12) | 0.145 (2) | 0.0372 (10) | 0.0201 (14) | 0.0066 (8) | −0.0047 (13) |
C15 | 0.0669 (14) | 0.0989 (17) | 0.0563 (13) | −0.0055 (12) | 0.0049 (10) | 0.0060 (12) |
C16 | 0.0630 (12) | 0.0754 (13) | 0.0476 (10) | 0.0065 (10) | 0.0011 (9) | −0.0115 (9) |
N1 | 0.0421 (7) | 0.0588 (8) | 0.0349 (7) | 0.0095 (6) | 0.0028 (5) | −0.0148 (6) |
N2 | 0.0468 (8) | 0.0666 (9) | 0.0367 (7) | 0.0076 (7) | 0.0064 (6) | −0.0165 (7) |
N3 | 0.0540 (9) | 0.0677 (10) | 0.0390 (8) | 0.0089 (7) | −0.0003 (6) | −0.0132 (7) |
O1 | 0.0464 (7) | 0.0661 (8) | 0.0835 (10) | 0.0109 (6) | −0.0094 (6) | −0.0316 (7) |
S1 | 0.0497 (3) | 0.0834 (4) | 0.0422 (3) | 0.0205 (2) | 0.00434 (19) | −0.0125 (2) |
Geometric parameters (Å, º) top
C1—N2 | 1.339 (2) | C8—H8 | 0.9300 |
C1—N1 | 1.371 (2) | C9—H9 | 0.9300 |
C1—S1 | 1.6703 (18) | C10—H10A | 0.9600 |
C2—N3 | 1.297 (2) | C10—H10B | 0.9600 |
C2—N1 | 1.376 (2) | C10—H10C | 0.9600 |
C2—C3 | 1.482 (2) | C11—C16 | 1.361 (3) |
C3—O1 | 1.423 (2) | C11—C12 | 1.378 (3) |
C3—H3A | 0.9700 | C11—N1 | 1.451 (2) |
C3—H3B | 0.9700 | C12—C13 | 1.390 (3) |
C4—C9 | 1.367 (3) | C12—H12 | 0.9300 |
C4—C5 | 1.375 (3) | C13—C14 | 1.352 (4) |
C4—O1 | 1.376 (2) | C13—H13 | 0.9300 |
C5—C6 | 1.378 (3) | C14—C15 | 1.370 (4) |
C5—H5 | 0.9300 | C14—H14 | 0.9300 |
C6—C7 | 1.369 (3) | C15—C16 | 1.388 (3) |
C6—H6 | 0.9300 | C15—H15 | 0.9300 |
C7—C8 | 1.370 (3) | C16—H16 | 0.9300 |
C7—C10 | 1.510 (3) | N2—N3 | 1.374 (2) |
C8—C9 | 1.384 (3) | N2—H2 | 0.88 (2) |
| | | |
N2—C1—N1 | 103.02 (15) | C7—C10—H10B | 109.5 |
N2—C1—S1 | 128.19 (13) | H10A—C10—H10B | 109.5 |
N1—C1—S1 | 128.79 (13) | C7—C10—H10C | 109.5 |
N3—C2—N1 | 111.37 (15) | H10A—C10—H10C | 109.5 |
N3—C2—C3 | 124.49 (16) | H10B—C10—H10C | 109.5 |
N1—C2—C3 | 124.13 (14) | C16—C11—C12 | 122.06 (17) |
O1—C3—C2 | 106.96 (15) | C16—C11—N1 | 118.90 (16) |
O1—C3—H3A | 110.3 | C12—C11—N1 | 119.04 (17) |
C2—C3—H3A | 110.3 | C11—C12—C13 | 118.0 (2) |
O1—C3—H3B | 110.3 | C11—C12—H12 | 121.0 |
C2—C3—H3B | 110.3 | C13—C12—H12 | 121.0 |
H3A—C3—H3B | 108.6 | C14—C13—C12 | 120.7 (2) |
C9—C4—C5 | 118.92 (17) | C14—C13—H13 | 119.6 |
C9—C4—O1 | 125.05 (17) | C12—C13—H13 | 119.6 |
C5—C4—O1 | 116.01 (17) | C13—C14—C15 | 120.5 (2) |
C4—C5—C6 | 120.2 (2) | C13—C14—H14 | 119.7 |
C4—C5—H5 | 119.9 | C15—C14—H14 | 119.7 |
C6—C5—H5 | 119.9 | C14—C15—C16 | 120.1 (2) |
C7—C6—C5 | 121.9 (2) | C14—C15—H15 | 119.9 |
C7—C6—H6 | 119.1 | C16—C15—H15 | 119.9 |
C5—C6—H6 | 119.1 | C11—C16—C15 | 118.6 (2) |
C6—C7—C8 | 117.07 (18) | C11—C16—H16 | 120.7 |
C6—C7—C10 | 121.1 (2) | C15—C16—H16 | 120.7 |
C8—C7—C10 | 121.8 (2) | C1—N1—C2 | 108.04 (13) |
C7—C8—C9 | 122.07 (18) | C1—N1—C11 | 125.91 (14) |
C7—C8—H8 | 119.0 | C2—N1—C11 | 125.93 (13) |
C9—C8—H8 | 119.0 | C1—N2—N3 | 114.01 (14) |
C4—C9—C8 | 119.84 (18) | C1—N2—H2 | 125.0 (14) |
C4—C9—H9 | 120.1 | N3—N2—H2 | 120.9 (14) |
C8—C9—H9 | 120.1 | C2—N3—N2 | 103.55 (14) |
C7—C10—H10A | 109.5 | C4—O1—C3 | 117.06 (14) |
| | | |
N3—C2—C3—O1 | 103.4 (2) | N2—C1—N1—C2 | −0.18 (18) |
N1—C2—C3—O1 | −77.0 (2) | S1—C1—N1—C2 | −179.86 (14) |
C9—C4—C5—C6 | −1.8 (3) | N2—C1—N1—C11 | −176.52 (16) |
O1—C4—C5—C6 | 179.7 (2) | S1—C1—N1—C11 | 3.8 (3) |
C4—C5—C6—C7 | 0.5 (4) | N3—C2—N1—C1 | 0.3 (2) |
C5—C6—C7—C8 | 1.4 (4) | C3—C2—N1—C1 | −179.29 (16) |
C5—C6—C7—C10 | −178.5 (2) | N3—C2—N1—C11 | 176.61 (16) |
C6—C7—C8—C9 | −2.0 (3) | C3—C2—N1—C11 | −3.0 (3) |
C10—C7—C8—C9 | 177.8 (2) | C16—C11—N1—C1 | 71.3 (2) |
C5—C4—C9—C8 | 1.2 (3) | C12—C11—N1—C1 | −109.6 (2) |
O1—C4—C9—C8 | 179.49 (17) | C16—C11—N1—C2 | −104.4 (2) |
C7—C8—C9—C4 | 0.8 (3) | C12—C11—N1—C2 | 74.7 (2) |
C16—C11—C12—C13 | −0.1 (3) | N1—C1—N2—N3 | 0.0 (2) |
N1—C11—C12—C13 | −179.16 (17) | S1—C1—N2—N3 | 179.73 (13) |
C11—C12—C13—C14 | −0.6 (3) | N1—C2—N3—N2 | −0.23 (19) |
C12—C13—C14—C15 | 0.9 (4) | C3—C2—N3—N2 | 179.33 (17) |
C13—C14—C15—C16 | −0.6 (4) | C1—N2—N3—C2 | 0.1 (2) |
C12—C11—C16—C15 | 0.5 (3) | C9—C4—O1—C3 | 16.8 (3) |
N1—C11—C16—C15 | 179.48 (18) | C5—C4—O1—C3 | −164.86 (18) |
C14—C15—C16—C11 | −0.1 (3) | C2—C3—O1—C4 | 162.35 (15) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···S1i | 0.88 (2) | 2.44 (2) | 3.3163 (18) | 175.9 (18) |
Symmetry code: (i) −x, −y+2, −z+1. |
π-π Interactions (Face-to-Face) topX (j) → X (k) | Dihedral angle (j, k) (°) | Distance between the barycenters (Å) |
X (1A) → X (1B)l | 0 | 4.116 |
X (1B) → X (1C)m | 0 | 4.864 |
Symmetry codes: (l) 1+x, y, z; (m) x, y, z |