Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024774/cf2105sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024774/cf2105Isup2.hkl |
CCDC reference: 654937
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.053
- wR factor = 0.135
- Data-to-parameter ratio = 14.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H4B .. S1 .. 2.99 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C18 H15 O P
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Triethylamine (0.024 mol, 2.42 g) was added to a mixture of triphenylphosphine (0.012 mol, 2.84 g), 4-amino-5-(2-ethoxyphenyl)-4H-1,2,4-triazole-3-thiol (0.008 mol) and dry acetonitrile (40 ml) at room temperature. The mixture was stirred for 5 h under reflux (Ding et al., 2004). The white solid was filtered off and recrystallized from ethanol. Yield 58%, m. p. 436–438 K.
H atoms attached to N atoms were located in a difference Fourier map, and refined with N—H distances restrained to 0.85 (1) Å with Uiso = 1.2Ueq(N). The other H atoms were positioned geometrically and allowed to ride on their parent atoms with C—H = 0.93–0.97 Å and Uiso = 1.2Ueq(C) or 1.5Ueq(methyl-C).
Recently, iminophosphoranes have attracted increasing attention as useful building blocks for nitrogen-containing heterocycles (Fresneda & Molina, 2004). Many interesting crystal structures involving iminophosphorane groups have been published, including some recent reports from our laboratory (Ding et al., 2005; Huang et al., 2005). As an extension of our research, we report the synthesis and crystal structure of the title compound (I), in which an iminophosphorane is not formed.
The molecular structure of (I) is shown in Fig. 1. The triazole ring (C20, C19, N1—N3) is planar with an r.m.s. deviation of 0.0066 Å, and makes a dihedral angle of 51.24 (7)° with the attached benzene group. The C—N bond lengths, in the range 1.305 (3) Å-1.370 (3) Å, are longer than a typical C=N bond [ca 1.269 (2) Å], but short than a typical C—N bond length [ca 1.443 (4) Å], indicating electron delocalization in the triazole ring (Jin et al., 2004).
The crystal packing (Fig. 2) is stabilized by an intramolecular N—H···O hydrogen bond, an intermolecular N—H···O hydrogen bond between the triazole ring and the triphenylphosphine oxide molecule, and intermolecular N—H···S hydrogen bonds, which can be described by the graph-set notation R22(8) (Xiong et al., 2005).
For related literature, see: Ding et al. (2004); Fresneda & Molina (2004); Huang et al. (2005); Jin et al. (2004); Xiong et al. (2005); Ding et al. (2005).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.
C18H15OP·C10H12N4OS | F(000) = 1080 |
Mr = 514.57 | Dx = 1.263 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5026 reflections |
a = 10.0514 (7) Å | θ = 2.4–25.1° |
b = 18.3008 (12) Å | µ = 0.21 mm−1 |
c = 15.285 (1) Å | T = 298 K |
β = 105.726 (1)° | Block, colourless |
V = 2706.4 (3) Å3 | 0.42 × 0.31 × 0.27 mm |
Z = 4 |
Bruker APEX area-detector diffractometer | 4857 independent reflections |
Radiation source: fine-focus sealed tube | 4255 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
φ and ω scans | θmax = 25.2°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −11→12 |
Tmin = 0.917, Tmax = 0.942 | k = −21→21 |
14188 measured reflections | l = −16→18 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.066P)2 + 0.984P] where P = (Fo2 + 2Fc2)/3 |
4857 reflections | (Δ/σ)max = 0.001 |
335 parameters | Δρmax = 0.27 e Å−3 |
3 restraints | Δρmin = −0.27 e Å−3 |
C18H15OP·C10H12N4OS | V = 2706.4 (3) Å3 |
Mr = 514.57 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.0514 (7) Å | µ = 0.21 mm−1 |
b = 18.3008 (12) Å | T = 298 K |
c = 15.285 (1) Å | 0.42 × 0.31 × 0.27 mm |
β = 105.726 (1)° |
Bruker APEX area-detector diffractometer | 4857 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 4255 reflections with I > 2σ(I) |
Tmin = 0.917, Tmax = 0.942 | Rint = 0.022 |
14188 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 3 restraints |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.27 e Å−3 |
4857 reflections | Δρmin = −0.27 e Å−3 |
335 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | −0.05775 (9) | 1.11318 (3) | 0.05669 (4) | 0.0669 (2) | |
P1 | −0.47530 (6) | 1.19485 (3) | 0.18357 (4) | 0.04240 (17) | |
O1 | −0.32154 (16) | 1.19058 (8) | 0.21438 (12) | 0.0549 (4) | |
O2 | −0.00016 (19) | 0.84581 (8) | 0.21677 (11) | 0.0632 (5) | |
N1 | 0.00551 (18) | 1.00791 (9) | 0.18675 (11) | 0.0419 (4) | |
N2 | −0.1418 (2) | 1.08364 (10) | 0.20819 (12) | 0.0466 (4) | |
N3 | −0.11670 (18) | 1.03653 (10) | 0.28068 (12) | 0.0455 (4) | |
N4 | 0.1115 (2) | 0.97627 (12) | 0.15487 (15) | 0.0583 (5) | |
C1 | −0.5478 (2) | 1.15002 (13) | 0.07667 (15) | 0.0503 (5) | |
C2 | −0.6097 (3) | 1.08207 (15) | 0.06990 (18) | 0.0673 (7) | |
H2 | −0.6204 | 1.0591 | 0.1218 | 0.081* | |
C3 | −0.6557 (3) | 1.04802 (19) | −0.0136 (2) | 0.0856 (9) | |
H3 | −0.6986 | 1.0026 | −0.0176 | 0.103* | |
C4 | −0.6389 (4) | 1.0803 (2) | −0.0896 (2) | 0.0906 (10) | |
H4 | −0.6699 | 1.0570 | −0.1456 | 0.109* | |
C5 | −0.5763 (4) | 1.1470 (2) | −0.0841 (2) | 0.0996 (12) | |
H5 | −0.5644 | 1.1689 | −0.1363 | 0.119* | |
C6 | −0.5307 (4) | 1.18205 (17) | −0.00140 (19) | 0.0796 (9) | |
H6 | −0.4882 | 1.2275 | 0.0018 | 0.096* | |
C7 | −0.5512 (2) | 1.15562 (11) | 0.26723 (14) | 0.0446 (5) | |
C8 | −0.4618 (3) | 1.13856 (15) | 0.35082 (16) | 0.0616 (6) | |
H8 | −0.3673 | 1.1458 | 0.3607 | 0.074* | |
C9 | −0.5120 (4) | 1.11093 (17) | 0.41956 (19) | 0.0786 (9) | |
H9 | −0.4513 | 1.0997 | 0.4756 | 0.094* | |
C10 | −0.6507 (4) | 1.10008 (15) | 0.40541 (19) | 0.0736 (8) | |
H10 | −0.6842 | 1.0811 | 0.4518 | 0.088* | |
C11 | −0.7405 (3) | 1.11694 (14) | 0.32346 (19) | 0.0636 (7) | |
H11 | −0.8348 | 1.1098 | 0.3145 | 0.076* | |
C12 | −0.6922 (2) | 1.14453 (13) | 0.25385 (16) | 0.0540 (6) | |
H12 | −0.7537 | 1.1557 | 0.1981 | 0.065* | |
C13 | −0.5308 (2) | 1.28893 (12) | 0.17058 (15) | 0.0446 (5) | |
C14 | −0.6686 (3) | 1.30798 (14) | 0.13743 (17) | 0.0586 (6) | |
H14 | −0.7351 | 1.2720 | 0.1171 | 0.070* | |
C15 | −0.7070 (3) | 1.38043 (17) | 0.1346 (2) | 0.0727 (8) | |
H15 | −0.7997 | 1.3931 | 0.1130 | 0.087* | |
C16 | −0.6100 (4) | 1.43355 (16) | 0.1632 (2) | 0.0786 (9) | |
H16 | −0.6369 | 1.4823 | 0.1611 | 0.094* | |
C17 | −0.4741 (4) | 1.41562 (15) | 0.1947 (2) | 0.0786 (8) | |
H17 | −0.4082 | 1.4522 | 0.2133 | 0.094* | |
C18 | −0.4333 (3) | 1.34315 (13) | 0.19924 (18) | 0.0602 (6) | |
H18 | −0.3404 | 1.3310 | 0.2216 | 0.072* | |
C19 | −0.0680 (2) | 1.06811 (11) | 0.15007 (14) | 0.0442 (5) | |
C20 | −0.0245 (2) | 0.99114 (11) | 0.26665 (14) | 0.0400 (5) | |
C21 | 0.0393 (2) | 0.93404 (11) | 0.33202 (15) | 0.0428 (5) | |
C22 | 0.0484 (2) | 0.86112 (12) | 0.30667 (16) | 0.0489 (5) | |
C23 | 0.1019 (3) | 0.80937 (13) | 0.3740 (2) | 0.0620 (7) | |
H23 | 0.1101 | 0.7609 | 0.3578 | 0.074* | |
C24 | 0.1424 (3) | 0.82924 (16) | 0.46318 (19) | 0.0673 (7) | |
H24 | 0.1777 | 0.7941 | 0.5073 | 0.081* | |
C25 | 0.1316 (3) | 0.90041 (15) | 0.48875 (18) | 0.0626 (7) | |
H25 | 0.1578 | 0.9133 | 0.5499 | 0.075* | |
C26 | 0.0816 (2) | 0.95263 (13) | 0.42319 (15) | 0.0504 (5) | |
H26 | 0.0762 | 1.0010 | 0.4404 | 0.060* | |
C27 | −0.0126 (4) | 0.77064 (15) | 0.1900 (2) | 0.0777 (8) | |
H27A | −0.0690 | 0.7448 | 0.2223 | 0.093* | |
H27B | 0.0780 | 0.7480 | 0.2048 | 0.093* | |
C28 | −0.0768 (4) | 0.76641 (18) | 0.0916 (2) | 0.0938 (11) | |
H28A | −0.1676 | 0.7875 | 0.0777 | 0.141* | |
H28B | −0.0834 | 0.7162 | 0.0727 | 0.141* | |
H28C | −0.0213 | 0.7928 | 0.0601 | 0.141* | |
H2A | −0.202 (3) | 1.1183 (15) | 0.203 (2) | 0.113* | |
H4A | 0.123 (4) | 1.0041 (17) | 0.113 (2) | 0.113* | |
H4B | 0.078 (4) | 0.9357 (14) | 0.133 (2) | 0.113* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.1072 (6) | 0.0476 (4) | 0.0524 (4) | 0.0064 (3) | 0.0329 (4) | 0.0079 (3) |
P1 | 0.0379 (3) | 0.0395 (3) | 0.0503 (3) | 0.0045 (2) | 0.0128 (2) | −0.0017 (2) |
O1 | 0.0421 (9) | 0.0480 (9) | 0.0748 (11) | 0.0070 (7) | 0.0162 (8) | −0.0034 (8) |
O2 | 0.0910 (13) | 0.0364 (9) | 0.0617 (11) | 0.0011 (8) | 0.0197 (9) | −0.0026 (7) |
N1 | 0.0504 (10) | 0.0344 (9) | 0.0447 (10) | 0.0030 (7) | 0.0196 (8) | −0.0039 (7) |
N2 | 0.0535 (11) | 0.0385 (10) | 0.0504 (10) | 0.0088 (8) | 0.0187 (9) | 0.0020 (8) |
N3 | 0.0494 (11) | 0.0413 (10) | 0.0494 (10) | 0.0056 (8) | 0.0194 (8) | 0.0027 (8) |
N4 | 0.0686 (14) | 0.0513 (12) | 0.0663 (14) | 0.0110 (10) | 0.0374 (11) | −0.0013 (10) |
C1 | 0.0493 (13) | 0.0529 (14) | 0.0502 (13) | 0.0053 (10) | 0.0162 (10) | −0.0052 (10) |
C2 | 0.0782 (19) | 0.0658 (17) | 0.0614 (16) | −0.0144 (14) | 0.0251 (14) | −0.0152 (13) |
C3 | 0.091 (2) | 0.088 (2) | 0.079 (2) | −0.0216 (18) | 0.0246 (17) | −0.0317 (17) |
C4 | 0.102 (3) | 0.111 (3) | 0.0597 (18) | −0.001 (2) | 0.0222 (17) | −0.0295 (18) |
C5 | 0.141 (3) | 0.109 (3) | 0.0576 (19) | −0.006 (3) | 0.043 (2) | −0.0051 (18) |
C6 | 0.112 (3) | 0.075 (2) | 0.0610 (17) | −0.0117 (17) | 0.0393 (17) | −0.0036 (14) |
C7 | 0.0491 (12) | 0.0385 (11) | 0.0462 (12) | 0.0010 (9) | 0.0131 (10) | −0.0054 (9) |
C8 | 0.0617 (15) | 0.0677 (16) | 0.0505 (14) | −0.0018 (13) | 0.0068 (12) | 0.0051 (12) |
C9 | 0.092 (2) | 0.087 (2) | 0.0507 (16) | −0.0075 (17) | 0.0095 (15) | 0.0084 (14) |
C10 | 0.105 (3) | 0.0665 (18) | 0.0582 (17) | −0.0149 (16) | 0.0380 (17) | −0.0036 (13) |
C11 | 0.0674 (17) | 0.0603 (16) | 0.0705 (17) | −0.0121 (13) | 0.0315 (14) | −0.0101 (13) |
C12 | 0.0522 (14) | 0.0577 (14) | 0.0522 (13) | −0.0037 (11) | 0.0143 (11) | −0.0035 (11) |
C13 | 0.0477 (12) | 0.0426 (11) | 0.0477 (12) | 0.0080 (9) | 0.0203 (10) | 0.0024 (9) |
C14 | 0.0526 (14) | 0.0602 (15) | 0.0654 (16) | 0.0129 (11) | 0.0203 (12) | 0.0118 (12) |
C15 | 0.0731 (18) | 0.074 (2) | 0.0811 (19) | 0.0350 (16) | 0.0383 (15) | 0.0259 (15) |
C16 | 0.115 (3) | 0.0485 (16) | 0.087 (2) | 0.0277 (17) | 0.052 (2) | 0.0133 (14) |
C17 | 0.102 (2) | 0.0459 (15) | 0.094 (2) | −0.0025 (15) | 0.0372 (19) | −0.0028 (14) |
C18 | 0.0594 (15) | 0.0482 (14) | 0.0754 (17) | 0.0023 (12) | 0.0225 (13) | −0.0009 (12) |
C19 | 0.0544 (13) | 0.0338 (11) | 0.0447 (12) | −0.0016 (9) | 0.0138 (10) | −0.0036 (9) |
C20 | 0.0432 (11) | 0.0350 (11) | 0.0437 (11) | −0.0020 (9) | 0.0150 (9) | −0.0032 (8) |
C21 | 0.0397 (11) | 0.0391 (11) | 0.0529 (13) | 0.0015 (9) | 0.0180 (9) | 0.0043 (9) |
C22 | 0.0482 (13) | 0.0434 (12) | 0.0569 (14) | 0.0019 (10) | 0.0173 (11) | 0.0013 (10) |
C23 | 0.0663 (16) | 0.0409 (13) | 0.0795 (18) | 0.0082 (11) | 0.0211 (14) | 0.0110 (12) |
C24 | 0.0645 (17) | 0.0683 (18) | 0.0660 (17) | 0.0109 (13) | 0.0124 (13) | 0.0227 (14) |
C25 | 0.0578 (15) | 0.0746 (18) | 0.0519 (14) | 0.0040 (13) | 0.0086 (12) | 0.0092 (13) |
C26 | 0.0473 (13) | 0.0524 (13) | 0.0515 (13) | 0.0007 (10) | 0.0135 (10) | 0.0010 (10) |
C27 | 0.102 (2) | 0.0452 (15) | 0.085 (2) | −0.0095 (15) | 0.0244 (17) | −0.0081 (14) |
C28 | 0.140 (3) | 0.070 (2) | 0.081 (2) | −0.016 (2) | 0.046 (2) | −0.0201 (17) |
S1—C19 | 1.676 (2) | C10—C11 | 1.366 (4) |
P1—O1 | 1.4906 (16) | C10—H10 | 0.930 |
P1—C1 | 1.797 (2) | C11—C12 | 1.380 (3) |
P1—C13 | 1.804 (2) | C11—H11 | 0.930 |
P1—C7 | 1.806 (2) | C12—H12 | 0.930 |
O2—C22 | 1.357 (3) | C13—C18 | 1.379 (3) |
O2—C27 | 1.431 (3) | C13—C14 | 1.384 (3) |
N1—C19 | 1.360 (3) | C14—C15 | 1.378 (4) |
N1—C20 | 1.370 (3) | C14—H14 | 0.930 |
N1—N4 | 1.410 (3) | C15—C16 | 1.362 (5) |
N2—C19 | 1.334 (3) | C15—H15 | 0.930 |
N2—N3 | 1.372 (2) | C16—C17 | 1.360 (5) |
N2—H2A | 0.862 (18) | C16—H16 | 0.930 |
N3—C20 | 1.305 (3) | C17—C18 | 1.384 (4) |
N4—H4A | 0.846 (18) | C17—H17 | 0.930 |
N4—H4B | 0.847 (18) | C18—H18 | 0.930 |
C1—C6 | 1.381 (4) | C20—C21 | 1.468 (3) |
C1—C2 | 1.382 (4) | C21—C26 | 1.385 (3) |
C2—C3 | 1.383 (4) | C21—C22 | 1.399 (3) |
C2—H2 | 0.930 | C22—C23 | 1.394 (3) |
C3—C4 | 1.354 (5) | C23—C24 | 1.362 (4) |
C3—H3 | 0.930 | C23—H23 | 0.930 |
C4—C5 | 1.365 (5) | C24—C25 | 1.373 (4) |
C4—H4 | 0.930 | C24—H24 | 0.930 |
C5—C6 | 1.380 (4) | C25—C26 | 1.377 (3) |
C5—H5 | 0.930 | C25—H25 | 0.930 |
C6—H6 | 0.930 | C26—H26 | 0.930 |
C7—C8 | 1.384 (3) | C27—C28 | 1.469 (4) |
C7—C12 | 1.390 (3) | C27—H27A | 0.970 |
C8—C9 | 1.379 (4) | C27—H27B | 0.970 |
C8—H8 | 0.930 | C28—H28A | 0.960 |
C9—C10 | 1.367 (4) | C28—H28B | 0.960 |
C9—H9 | 0.930 | C28—H28C | 0.960 |
O1—P1—C1 | 113.18 (10) | C18—C13—P1 | 118.67 (18) |
O1—P1—C13 | 110.35 (10) | C14—C13—P1 | 121.96 (19) |
C1—P1—C13 | 107.37 (11) | C15—C14—C13 | 119.8 (3) |
O1—P1—C7 | 110.87 (10) | C15—C14—H14 | 120.1 |
C1—P1—C7 | 108.51 (10) | C13—C14—H14 | 120.1 |
C13—P1—C7 | 106.26 (10) | C16—C15—C14 | 120.4 (3) |
C22—O2—C27 | 117.9 (2) | C16—C15—H15 | 119.8 |
C19—N1—C20 | 108.82 (17) | C14—C15—H15 | 119.8 |
C19—N1—N4 | 124.54 (18) | C17—C16—C15 | 120.3 (3) |
C20—N1—N4 | 125.86 (18) | C17—C16—H16 | 119.9 |
C19—N2—N3 | 112.96 (17) | C15—C16—H16 | 119.9 |
C19—N2—H2A | 126 (2) | C16—C17—C18 | 120.3 (3) |
N3—N2—H2A | 121 (2) | C16—C17—H17 | 119.9 |
C20—N3—N2 | 104.53 (16) | C18—C17—H17 | 119.9 |
N1—N4—H4A | 106 (3) | C13—C18—C17 | 119.9 (3) |
N1—N4—H4B | 104 (3) | C13—C18—H18 | 120.1 |
H4A—N4—H4B | 111 (3) | C17—C18—H18 | 120.1 |
C6—C1—C2 | 118.4 (2) | N2—C19—N1 | 103.67 (17) |
C6—C1—P1 | 118.5 (2) | N2—C19—S1 | 129.52 (17) |
C2—C1—P1 | 122.85 (19) | N1—C19—S1 | 126.73 (17) |
C1—C2—C3 | 120.4 (3) | N3—C20—N1 | 109.98 (18) |
C1—C2—H2 | 119.8 | N3—C20—C21 | 122.72 (18) |
C3—C2—H2 | 119.8 | N1—C20—C21 | 127.22 (18) |
C4—C3—C2 | 120.5 (3) | C26—C21—C22 | 119.2 (2) |
C4—C3—H3 | 119.8 | C26—C21—C20 | 117.93 (19) |
C2—C3—H3 | 119.8 | C22—C21—C20 | 122.7 (2) |
C3—C4—C5 | 120.0 (3) | O2—C22—C23 | 124.6 (2) |
C3—C4—H4 | 120.0 | O2—C22—C21 | 116.40 (19) |
C5—C4—H4 | 120.0 | C23—C22—C21 | 119.0 (2) |
C4—C5—C6 | 120.4 (3) | C24—C23—C22 | 120.5 (2) |
C4—C5—H5 | 119.8 | C24—C23—H23 | 119.7 |
C6—C5—H5 | 119.8 | C22—C23—H23 | 119.7 |
C5—C6—C1 | 120.4 (3) | C23—C24—C25 | 120.9 (2) |
C5—C6—H6 | 119.8 | C23—C24—H24 | 119.6 |
C1—C6—H6 | 119.8 | C25—C24—H24 | 119.6 |
C8—C7—C12 | 118.9 (2) | C24—C25—C26 | 119.5 (2) |
C8—C7—P1 | 116.74 (18) | C24—C25—H25 | 120.2 |
C12—C7—P1 | 124.27 (17) | C26—C25—H25 | 120.2 |
C9—C8—C7 | 120.4 (3) | C25—C26—C21 | 120.9 (2) |
C9—C8—H8 | 119.8 | C25—C26—H26 | 119.5 |
C7—C8—H8 | 119.8 | C21—C26—H26 | 119.5 |
C10—C9—C8 | 120.1 (3) | O2—C27—C28 | 108.9 (2) |
C10—C9—H9 | 120.0 | O2—C27—H27A | 109.9 |
C8—C9—H9 | 120.0 | C28—C27—H27A | 109.9 |
C11—C10—C9 | 120.3 (3) | O2—C27—H27B | 109.9 |
C11—C10—H10 | 119.9 | C28—C27—H27B | 109.9 |
C9—C10—H10 | 119.9 | H27A—C27—H27B | 108.3 |
C10—C11—C12 | 120.5 (3) | C27—C28—H28A | 109.5 |
C10—C11—H11 | 119.8 | C27—C28—H28B | 109.5 |
C12—C11—H11 | 119.8 | H28A—C28—H28B | 109.5 |
C11—C12—C7 | 119.8 (2) | C27—C28—H28C | 109.5 |
C11—C12—H12 | 120.1 | H28A—C28—H28C | 109.5 |
C7—C12—H12 | 120.1 | H28B—C28—H28C | 109.5 |
C18—C13—C14 | 119.3 (2) | ||
C19—N2—N3—C20 | 0.2 (2) | C13—C14—C15—C16 | 0.8 (4) |
O1—P1—C1—C6 | −71.7 (2) | C14—C15—C16—C17 | 0.1 (4) |
C13—P1—C1—C6 | 50.3 (2) | C15—C16—C17—C18 | −0.9 (5) |
C7—P1—C1—C6 | 164.8 (2) | C14—C13—C18—C17 | 0.1 (4) |
O1—P1—C1—C2 | 102.7 (2) | P1—C13—C18—C17 | −176.5 (2) |
C13—P1—C1—C2 | −135.2 (2) | C16—C17—C18—C13 | 0.8 (4) |
C7—P1—C1—C2 | −20.8 (2) | N3—N2—C19—N1 | 0.9 (2) |
C6—C1—C2—C3 | −1.3 (4) | N3—N2—C19—S1 | −175.86 (17) |
P1—C1—C2—C3 | −175.8 (2) | C20—N1—C19—N2 | −1.7 (2) |
C1—C2—C3—C4 | 1.0 (5) | N4—N1—C19—N2 | −172.0 (2) |
C2—C3—C4—C5 | −0.1 (6) | C20—N1—C19—S1 | 175.21 (16) |
C3—C4—C5—C6 | −0.4 (6) | N4—N1—C19—S1 | 4.9 (3) |
C4—C5—C6—C1 | 0.0 (6) | N2—N3—C20—N1 | −1.3 (2) |
C2—C1—C6—C5 | 0.8 (5) | N2—N3—C20—C21 | 175.65 (19) |
P1—C1—C6—C5 | 175.5 (3) | C19—N1—C20—N3 | 2.0 (2) |
O1—P1—C7—C8 | 9.8 (2) | N4—N1—C20—N3 | 172.1 (2) |
C1—P1—C7—C8 | 134.69 (19) | C19—N1—C20—C21 | −174.8 (2) |
C13—P1—C7—C8 | −110.12 (19) | N4—N1—C20—C21 | −4.7 (3) |
O1—P1—C7—C12 | −172.82 (18) | N3—C20—C21—C26 | −43.7 (3) |
C1—P1—C7—C12 | −47.9 (2) | N1—C20—C21—C26 | 132.7 (2) |
C13—P1—C7—C12 | 67.3 (2) | N3—C20—C21—C22 | 130.9 (2) |
C12—C7—C8—C9 | 0.1 (4) | N1—C20—C21—C22 | −52.7 (3) |
P1—C7—C8—C9 | 177.6 (2) | C27—O2—C22—C23 | 7.7 (4) |
C7—C8—C9—C10 | 0.1 (4) | C27—O2—C22—C21 | −170.5 (2) |
C8—C9—C10—C11 | −0.4 (5) | C26—C21—C22—O2 | 177.25 (19) |
C9—C10—C11—C12 | 0.5 (4) | C20—C21—C22—O2 | 2.7 (3) |
C10—C11—C12—C7 | −0.3 (4) | C26—C21—C22—C23 | −1.1 (3) |
C8—C7—C12—C11 | 0.0 (3) | C20—C21—C22—C23 | −175.6 (2) |
P1—C7—C12—C11 | −177.30 (19) | O2—C22—C23—C24 | −176.9 (2) |
O1—P1—C13—C18 | −7.5 (2) | C21—C22—C23—C24 | 1.3 (4) |
C1—P1—C13—C18 | −131.23 (19) | C22—C23—C24—C25 | −0.1 (4) |
C7—P1—C13—C18 | 112.81 (19) | C23—C24—C25—C26 | −1.2 (4) |
O1—P1—C13—C14 | 176.10 (19) | C24—C25—C26—C21 | 1.4 (4) |
C1—P1—C13—C14 | 52.3 (2) | C22—C21—C26—C25 | −0.3 (3) |
C7—P1—C13—C14 | −63.6 (2) | C20—C21—C26—C25 | 174.5 (2) |
C18—C13—C14—C15 | −0.9 (4) | C22—O2—C27—C28 | 175.6 (2) |
P1—C13—C14—C15 | 175.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 (2) | 1.83 (2) | 2.682 (2) | 169 (3) |
N4—H4A···S1 | 0.85 (2) | 2.68 (3) | 3.169 (2) | 118 (3) |
N4—H4B···O2 | 0.85 (2) | 2.35 (3) | 2.904 (3) | 124 (3) |
N4—H4B···S1i | 0.85 (2) | 2.99 (3) | 3.533 (2) | 124 (3) |
Symmetry code: (i) −x, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | C18H15OP·C10H12N4OS |
Mr | 514.57 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 10.0514 (7), 18.3008 (12), 15.285 (1) |
β (°) | 105.726 (1) |
V (Å3) | 2706.4 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.42 × 0.31 × 0.27 |
Data collection | |
Diffractometer | Bruker APEX area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.917, 0.942 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14188, 4857, 4255 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.600 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.135, 1.08 |
No. of reflections | 4857 |
No. of parameters | 335 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.27, −0.27 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2002), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.862 (18) | 1.830 (19) | 2.682 (2) | 169 (3) |
N4—H4A···S1 | 0.846 (18) | 2.68 (3) | 3.169 (2) | 118 (3) |
N4—H4B···O2 | 0.847 (18) | 2.35 (3) | 2.904 (3) | 124 (3) |
N4—H4B···S1i | 0.847 (18) | 2.99 (3) | 3.533 (2) | 124 (3) |
Symmetry code: (i) −x, −y+2, −z. |
Recently, iminophosphoranes have attracted increasing attention as useful building blocks for nitrogen-containing heterocycles (Fresneda & Molina, 2004). Many interesting crystal structures involving iminophosphorane groups have been published, including some recent reports from our laboratory (Ding et al., 2005; Huang et al., 2005). As an extension of our research, we report the synthesis and crystal structure of the title compound (I), in which an iminophosphorane is not formed.
The molecular structure of (I) is shown in Fig. 1. The triazole ring (C20, C19, N1—N3) is planar with an r.m.s. deviation of 0.0066 Å, and makes a dihedral angle of 51.24 (7)° with the attached benzene group. The C—N bond lengths, in the range 1.305 (3) Å-1.370 (3) Å, are longer than a typical C=N bond [ca 1.269 (2) Å], but short than a typical C—N bond length [ca 1.443 (4) Å], indicating electron delocalization in the triazole ring (Jin et al., 2004).
The crystal packing (Fig. 2) is stabilized by an intramolecular N—H···O hydrogen bond, an intermolecular N—H···O hydrogen bond between the triazole ring and the triphenylphosphine oxide molecule, and intermolecular N—H···S hydrogen bonds, which can be described by the graph-set notation R22(8) (Xiong et al., 2005).