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The structure of the title compound, C
23H
19N
3O
3, has been determined as part of our study on the synthesis and crystallography of triazole derivatives. The hydroxyl group is involved in an O—H
N intermolecular interaction.
Supporting information
CCDC reference: 605231
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.047
- wR factor = 0.115
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.97 Deg.
| Author Response: The entire data has been collected in the theta range of
2.25 to 24.97 Deg and MoKa radiation has been used for data collection.
Usually the theta range for the data collection with MoKa radiation is
2-25 Deg. The value of sin(thata)/lambda is 0.594 which is quite close to
0.6 (i.e. 25 degrees MoKa).
|
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.87 Ratio
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc.
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.75 Ratio
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
2 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
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PARST95 (Nardelli, 1995).
2-[3-(Methylphenoxymethyl)-5-phenyl-4
H-1,2,4-triazol-4-yl]benzoic acid
top
Crystal data top
C23H19N3O3 | Dx = 1.264 Mg m−3 |
Mr = 385.41 | Melting point: 573 K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 25 reflections |
a = 13.589 (9) Å | θ = 5.9–12.5° |
b = 18.546 (6) Å | µ = 0.09 mm−1 |
c = 16.075 (8) Å | T = 295 K |
V = 4051 (4) Å3 | Prism, light yellow |
Z = 8 | 0.5 × 0.45 × 0.3 mm |
F(000) = 1616 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.2° |
Graphite monochromator | h = 0→16 |
ω/2θ scans | k = 0→22 |
3548 measured reflections | l = 0→19 |
3548 independent reflections | 2 standard reflections every 60 min |
1595 reflections with I > 2σ(I) | intensity decay: <2% |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 0.90 | w = 1/[σ2(Fo2) + (0.0538P)2] where P = (Fo2 + 2Fc2)/3 |
3548 reflections | (Δ/σ)max < 0.001 |
263 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
Special details top
Experimental. A mixture of anthranilic acid (0.1 mol) and benzoyl chloride (0.1 mol) in
benzene (30 ml),trimethyl amine (0.5 ml) was heated on water bath for 3 h. The
solution then cooled and separated solid was filtered and further
recrystallized from ethanol to get 2-phenyl-3,1-benzoxazin-4-one. The mixture
of 2-phenyl-3-benzoxazin-4-one (0.1 mol) and m-methylphenoxyacetic acid
hydrazide (0.1 mol) in methanol was refluxed for 6 h, cooled and separated
solid filtered and recrystallized from ethanol. |
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 | |
N1 | 0.40251 (14) | 0.25636 (10) | 0.11547 (10) | 0.0352 (5) | |
C2 | 0.37042 (18) | 0.19196 (13) | 0.14590 (14) | 0.0373 (6) | |
N3 | 0.31497 (16) | 0.20286 (11) | 0.21181 (12) | 0.0455 (6) | |
N4 | 0.31333 (15) | 0.27583 (11) | 0.22549 (11) | 0.0437 (6) | |
C5 | 0.36745 (18) | 0.30780 (13) | 0.16840 (13) | 0.0357 (6) | |
C6 | 0.38869 (19) | 0.38495 (13) | 0.16812 (15) | 0.0431 (7) | |
C7 | 0.3929 (2) | 0.42641 (16) | 0.09600 (17) | 0.0604 (8) | |
H7 | 0.3848 | 0.4046 | 0.0444 | 0.073* | |
C8 | 0.4087 (3) | 0.49930 (17) | 0.1008 (2) | 0.0813 (11) | |
H8 | 0.4108 | 0.5267 | 0.0524 | 0.098* | |
C9 | 0.4217 (3) | 0.53250 (18) | 0.1772 (3) | 0.0877 (12) | |
H9 | 0.4324 | 0.5820 | 0.1802 | 0.105* | |
C10 | 0.4186 (3) | 0.49159 (16) | 0.2485 (2) | 0.0881 (12) | |
H10 | 0.4279 | 0.5134 | 0.3000 | 0.106* | |
C11 | 0.4020 (2) | 0.41924 (15) | 0.24390 (17) | 0.0666 (9) | |
H11 | 0.3995 | 0.3923 | 0.2927 | 0.080* | |
C12 | 0.46951 (17) | 0.26582 (12) | 0.04565 (13) | 0.0316 (6) | |
C13 | 0.42874 (18) | 0.26027 (14) | −0.03367 (14) | 0.0452 (7) | |
H13 | 0.3619 | 0.2513 | −0.0404 | 0.054* | |
C14 | 0.4895 (2) | 0.26839 (14) | −0.10219 (14) | 0.0471 (7) | |
H14 | 0.4634 | 0.2637 | −0.1554 | 0.057* | |
C15 | 0.58745 (19) | 0.28331 (13) | −0.09241 (14) | 0.0418 (7) | |
H15 | 0.6273 | 0.2893 | −0.1389 | 0.050* | |
C16 | 0.62760 (19) | 0.28955 (13) | −0.01305 (13) | 0.0396 (7) | |
H16 | 0.6939 | 0.3008 | −0.0066 | 0.048* | |
C17 | 0.56829 (17) | 0.27887 (12) | 0.05712 (12) | 0.0310 (6) | |
C18 | 0.6148 (2) | 0.27850 (14) | 0.14208 (14) | 0.0402 (6) | |
C19 | 0.3948 (2) | 0.11970 (13) | 0.11340 (15) | 0.0470 (7) | |
H19A | 0.4647 | 0.1166 | 0.1018 | 0.056* | |
H19B | 0.3784 | 0.0832 | 0.1544 | 0.056* | |
C20 | 0.3338 (2) | 0.03838 (14) | 0.01022 (17) | 0.0499 (8) | |
C21 | 0.2723 (2) | 0.02995 (16) | −0.05767 (17) | 0.0604 (9) | |
H21 | 0.2409 | 0.0700 | −0.0803 | 0.073* | |
C22 | 0.2571 (3) | −0.03735 (18) | −0.0922 (2) | 0.0722 (10) | |
C23 | 0.3043 (3) | −0.09579 (18) | −0.0571 (2) | 0.0823 (11) | |
H23 | 0.2940 | −0.1416 | −0.0790 | 0.099* | |
C24 | 0.3657 (3) | −0.08754 (16) | 0.0090 (2) | 0.0824 (11) | |
H24 | 0.3979 | −0.1276 | 0.0307 | 0.099* | |
C25 | 0.3809 (2) | −0.02035 (15) | 0.04461 (19) | 0.0681 (9) | |
H25 | 0.4218 | −0.0150 | 0.0906 | 0.082* | |
C26 | 0.1879 (3) | −0.0459 (2) | −0.1647 (2) | 0.1201 (16) | |
H26A | 0.1843 | −0.0958 | −0.1801 | 0.180* | |
H26B | 0.2116 | −0.0182 | −0.2110 | 0.180* | |
H26C | 0.1236 | −0.0291 | −0.1491 | 0.180* | |
O1 | 0.70514 (14) | 0.30179 (10) | 0.14115 (10) | 0.0591 (6) | |
H1 | 0.7277 | 0.3007 | 0.1885 | 0.089* | |
O2 | 0.57509 (14) | 0.25433 (12) | 0.20312 (10) | 0.0758 (7) | |
O3 | 0.34037 (15) | 0.10771 (9) | 0.03936 (11) | 0.0598 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0390 (12) | 0.0491 (13) | 0.0176 (10) | −0.0034 (11) | 0.0035 (10) | −0.0005 (9) |
C2 | 0.0369 (16) | 0.0500 (15) | 0.0250 (13) | −0.0054 (13) | 0.0011 (13) | 0.0008 (13) |
N3 | 0.0529 (16) | 0.0540 (15) | 0.0297 (12) | −0.0047 (12) | 0.0063 (11) | 0.0023 (10) |
N4 | 0.0515 (16) | 0.0525 (13) | 0.0272 (12) | −0.0073 (12) | 0.0059 (11) | −0.0016 (10) |
C5 | 0.0366 (15) | 0.0509 (16) | 0.0197 (12) | −0.0028 (13) | −0.0002 (12) | −0.0011 (12) |
C6 | 0.0428 (18) | 0.0489 (17) | 0.0376 (15) | −0.0022 (14) | 0.0045 (14) | −0.0023 (13) |
C7 | 0.074 (2) | 0.060 (2) | 0.0469 (18) | −0.0052 (17) | −0.0057 (17) | 0.0109 (16) |
C8 | 0.099 (3) | 0.066 (2) | 0.079 (3) | −0.008 (2) | −0.012 (2) | 0.026 (2) |
C9 | 0.098 (3) | 0.053 (2) | 0.112 (3) | −0.011 (2) | 0.004 (3) | −0.002 (2) |
C10 | 0.127 (4) | 0.063 (2) | 0.074 (2) | −0.020 (2) | 0.010 (2) | −0.019 (2) |
C11 | 0.097 (3) | 0.062 (2) | 0.0405 (17) | −0.0155 (19) | 0.0025 (17) | −0.0085 (16) |
C12 | 0.0292 (15) | 0.0455 (15) | 0.0200 (13) | −0.0025 (12) | 0.0018 (11) | 0.0017 (11) |
C13 | 0.0387 (17) | 0.0720 (19) | 0.0250 (13) | −0.0103 (15) | −0.0047 (12) | −0.0011 (13) |
C14 | 0.0563 (19) | 0.0694 (19) | 0.0156 (13) | −0.0036 (15) | −0.0022 (13) | −0.0004 (13) |
C15 | 0.0468 (18) | 0.0604 (16) | 0.0184 (12) | −0.0015 (14) | 0.0073 (13) | 0.0037 (12) |
C16 | 0.0383 (17) | 0.0541 (16) | 0.0265 (14) | −0.0025 (13) | 0.0025 (12) | 0.0063 (11) |
C17 | 0.0318 (15) | 0.0441 (14) | 0.0170 (12) | 0.0002 (12) | −0.0009 (11) | 0.0013 (10) |
C18 | 0.0373 (17) | 0.0589 (16) | 0.0242 (14) | −0.0030 (13) | −0.0042 (13) | 0.0023 (12) |
C19 | 0.0528 (19) | 0.0511 (17) | 0.0371 (16) | 0.0006 (15) | −0.0023 (14) | 0.0028 (13) |
C20 | 0.060 (2) | 0.0393 (17) | 0.0501 (18) | 0.0022 (15) | 0.0061 (16) | −0.0063 (14) |
C21 | 0.076 (2) | 0.0579 (18) | 0.0477 (17) | 0.0038 (17) | −0.0004 (17) | −0.0136 (15) |
C22 | 0.076 (3) | 0.069 (2) | 0.072 (2) | −0.005 (2) | 0.005 (2) | −0.029 (2) |
C23 | 0.085 (3) | 0.054 (2) | 0.107 (3) | −0.002 (2) | 0.016 (2) | −0.033 (2) |
C24 | 0.089 (3) | 0.044 (2) | 0.114 (3) | 0.0069 (18) | 0.001 (3) | −0.0053 (19) |
C25 | 0.082 (3) | 0.0527 (19) | 0.069 (2) | 0.0072 (18) | −0.0029 (19) | −0.0038 (17) |
C26 | 0.104 (4) | 0.136 (4) | 0.121 (3) | −0.010 (3) | −0.021 (3) | −0.073 (3) |
O1 | 0.0533 (13) | 0.0961 (15) | 0.0278 (10) | −0.0207 (11) | −0.0155 (9) | 0.0174 (10) |
O2 | 0.0495 (13) | 0.156 (2) | 0.0218 (10) | −0.0164 (14) | −0.0038 (9) | 0.0214 (12) |
O3 | 0.0900 (16) | 0.0457 (11) | 0.0436 (11) | 0.0032 (11) | −0.0219 (11) | −0.0091 (9) |
Geometric parameters (Å, º) top
N1—C2 | 1.362 (3) | C15—H15 | 0.9300 |
N1—C5 | 1.364 (3) | C16—C17 | 1.400 (3) |
N1—C12 | 1.456 (3) | C16—H16 | 0.9300 |
C2—N3 | 1.316 (3) | C17—C18 | 1.505 (3) |
C2—C19 | 1.476 (3) | C18—O2 | 1.206 (3) |
N3—N4 | 1.371 (3) | C18—O1 | 1.302 (3) |
N4—C5 | 1.317 (3) | C19—O3 | 1.419 (3) |
C5—C6 | 1.460 (3) | C19—H19A | 0.9700 |
C6—C11 | 1.386 (3) | C19—H19B | 0.9700 |
C6—C7 | 1.392 (3) | C20—O3 | 1.371 (3) |
C7—C8 | 1.371 (4) | C20—C25 | 1.379 (4) |
C7—H7 | 0.9300 | C20—C21 | 1.383 (4) |
C8—C9 | 1.384 (4) | C21—C22 | 1.382 (4) |
C8—H8 | 0.9300 | C21—H21 | 0.9300 |
C9—C10 | 1.375 (4) | C22—C23 | 1.381 (4) |
C9—H9 | 0.9300 | C22—C26 | 1.505 (4) |
C10—C11 | 1.363 (4) | C23—C24 | 1.359 (4) |
C10—H10 | 0.9300 | C23—H23 | 0.9300 |
C11—H11 | 0.9300 | C24—C25 | 1.387 (4) |
C12—C17 | 1.376 (3) | C24—H24 | 0.9300 |
C12—C13 | 1.394 (3) | C25—H25 | 0.9300 |
C13—C14 | 1.384 (3) | C26—H26A | 0.9600 |
C13—H13 | 0.9300 | C26—H26B | 0.9600 |
C14—C15 | 1.369 (3) | C26—H26C | 0.9600 |
C14—H14 | 0.9300 | O1—H1 | 0.8200 |
C15—C16 | 1.392 (3) | | |
| | | |
C2—N1—C5 | 106.10 (19) | C15—C16—C17 | 120.1 (2) |
C2—N1—C12 | 125.6 (2) | C15—C16—H16 | 120.0 |
C5—N1—C12 | 128.0 (2) | C17—C16—H16 | 120.0 |
N3—C2—N1 | 109.7 (2) | C12—C17—C16 | 118.6 (2) |
N3—C2—C19 | 123.6 (2) | C12—C17—C18 | 122.0 (2) |
N1—C2—C19 | 126.7 (2) | C16—C17—C18 | 119.4 (2) |
C2—N3—N4 | 106.9 (2) | O2—C18—O1 | 123.7 (2) |
C5—N4—N3 | 108.87 (19) | O2—C18—C17 | 123.6 (2) |
N4—C5—N1 | 108.4 (2) | O1—C18—C17 | 112.6 (2) |
N4—C5—C6 | 123.6 (2) | O3—C19—C2 | 108.8 (2) |
N1—C5—C6 | 127.9 (2) | O3—C19—H19A | 109.9 |
C11—C6—C7 | 118.2 (2) | C2—C19—H19A | 109.9 |
C11—C6—C5 | 118.2 (2) | O3—C19—H19B | 109.9 |
C7—C6—C5 | 123.5 (2) | C2—C19—H19B | 109.9 |
C8—C7—C6 | 120.2 (3) | H19A—C19—H19B | 108.3 |
C8—C7—H7 | 119.9 | O3—C20—C25 | 125.0 (3) |
C6—C7—H7 | 119.9 | O3—C20—C21 | 114.5 (2) |
C7—C8—C9 | 120.6 (3) | C25—C20—C21 | 120.5 (3) |
C7—C8—H8 | 119.7 | C22—C21—C20 | 120.7 (3) |
C9—C8—H8 | 119.7 | C22—C21—H21 | 119.7 |
C10—C9—C8 | 119.3 (3) | C20—C21—H21 | 119.7 |
C10—C9—H9 | 120.3 | C23—C22—C21 | 118.4 (3) |
C8—C9—H9 | 120.3 | C23—C22—C26 | 121.6 (3) |
C11—C10—C9 | 120.2 (3) | C21—C22—C26 | 120.0 (3) |
C11—C10—H10 | 119.9 | C24—C23—C22 | 121.1 (3) |
C9—C10—H10 | 119.9 | C24—C23—H23 | 119.4 |
C10—C11—C6 | 121.4 (3) | C22—C23—H23 | 119.4 |
C10—C11—H11 | 119.3 | C23—C24—C25 | 121.0 (3) |
C6—C11—H11 | 119.3 | C23—C24—H24 | 119.5 |
C17—C12—C13 | 121.5 (2) | C25—C24—H24 | 119.5 |
C17—C12—N1 | 121.85 (19) | C20—C25—C24 | 118.4 (3) |
C13—C12—N1 | 116.6 (2) | C20—C25—H25 | 120.8 |
C14—C13—C12 | 118.9 (2) | C24—C25—H25 | 120.8 |
C14—C13—H13 | 120.6 | C22—C26—H26A | 109.5 |
C12—C13—H13 | 120.6 | C22—C26—H26B | 109.5 |
C15—C14—C13 | 120.7 (2) | H26A—C26—H26B | 109.5 |
C15—C14—H14 | 119.7 | C22—C26—H26C | 109.5 |
C13—C14—H14 | 119.7 | H26A—C26—H26C | 109.5 |
C14—C15—C16 | 120.2 (2) | H26B—C26—H26C | 109.5 |
C14—C15—H15 | 119.9 | C18—O1—H1 | 109.5 |
C16—C15—H15 | 119.9 | C20—O3—C19 | 117.9 (2) |
| | | |
C5—N1—C2—N3 | 2.6 (3) | N1—C12—C13—C14 | −179.6 (2) |
C12—N1—C2—N3 | 176.6 (2) | C12—C13—C14—C15 | −1.5 (4) |
C5—N1—C2—C19 | −175.6 (2) | C13—C14—C15—C16 | 0.9 (4) |
C12—N1—C2—C19 | −1.6 (4) | C14—C15—C16—C17 | 1.5 (4) |
N1—C2—N3—N4 | −1.6 (3) | C13—C12—C17—C16 | 2.6 (4) |
C19—C2—N3—N4 | 176.7 (2) | N1—C12—C17—C16 | −178.1 (2) |
C2—N3—N4—C5 | −0.2 (3) | C13—C12—C17—C18 | −174.5 (2) |
N3—N4—C5—N1 | 1.8 (3) | N1—C12—C17—C18 | 4.8 (4) |
N3—N4—C5—C6 | −174.8 (2) | C15—C16—C17—C12 | −3.2 (3) |
C2—N1—C5—N4 | −2.7 (2) | C15—C16—C17—C18 | 174.0 (2) |
C12—N1—C5—N4 | −176.5 (2) | C12—C17—C18—O2 | 14.2 (4) |
C2—N1—C5—C6 | 173.7 (2) | C16—C17—C18—O2 | −162.9 (2) |
C12—N1—C5—C6 | −0.1 (4) | C12—C17—C18—O1 | −171.0 (2) |
N4—C5—C6—C11 | 35.8 (4) | C16—C17—C18—O1 | 12.0 (3) |
N1—C5—C6—C11 | −140.1 (3) | N3—C2—C19—O3 | 106.4 (3) |
N4—C5—C6—C7 | −141.8 (3) | N1—C2—C19—O3 | −75.6 (3) |
N1—C5—C6—C7 | 42.3 (4) | O3—C20—C21—C22 | −178.5 (3) |
C11—C6—C7—C8 | −0.7 (4) | C25—C20—C21—C22 | −0.1 (5) |
C5—C6—C7—C8 | 177.0 (3) | C20—C21—C22—C23 | 0.3 (5) |
C6—C7—C8—C9 | 0.6 (5) | C20—C21—C22—C26 | 178.4 (3) |
C7—C8—C9—C10 | 0.0 (6) | C21—C22—C23—C24 | −1.1 (5) |
C8—C9—C10—C11 | −0.6 (6) | C26—C22—C23—C24 | −179.1 (3) |
C9—C10—C11—C6 | 0.5 (6) | C22—C23—C24—C25 | 1.6 (6) |
C7—C6—C11—C10 | 0.1 (5) | O3—C20—C25—C24 | 178.8 (3) |
C5—C6—C11—C10 | −177.7 (3) | C21—C20—C25—C24 | 0.6 (5) |
C2—N1—C12—C17 | −99.2 (3) | C23—C24—C25—C20 | −1.4 (5) |
C5—N1—C12—C17 | 73.5 (3) | C25—C20—O3—C19 | −4.0 (4) |
C2—N1—C12—C13 | 80.1 (3) | C21—C20—O3—C19 | 174.4 (2) |
C5—N1—C12—C13 | −107.2 (3) | C2—C19—O3—C20 | −164.6 (2) |
C17—C12—C13—C14 | −0.2 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N4i | 0.82 | 1.87 | 2.644 (3) | 158 |
Symmetry code: (i) x+1/2, y, −z+1/2. |
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