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The title compound, C24H22N4O3, prepared by the reaction of 3,4,5-tri­methoxy­benz­aldehyde and 3,5-di­phenyl-4-amino-4H-1,2,4-triazole, crystallizes in a monoclinic space group, with one mol­ecule in the asymmetric unit. The crystal structure is stabilized mainly by van der Waals interactions, although a short intermolecular C...O contact of 3.156 (3) Å is also found.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803020270/cv6226sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803020270/cv6226Isup2.hkl
Contains datablock I

CCDC reference: 225777

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.041
  • wR factor = 0.097
  • Data-to-parameter ratio = 11.2

checkCIF/PLATON results

No syntax errors found



Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.743 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99 PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 - C14 = 6.77 su PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C24 H22 N4 O3
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 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1997) and PARST (Nardelli, 1995).

3,5-Diphenyl-4-(3,4,5-trimethoxybenzylidenamino)-4H-1,2,4-triazole top
Crystal data top
C24H22N4O3F(000) = 872
Mr = 414.46Dx = 1.281 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8342 reflections
a = 12.3359 (10) Åθ = 1.6–30.4°
b = 12.5288 (12) ŵ = 0.09 mm1
c = 13.9855 (11) ÅT = 293 K
β = 96.272 (6)°Prism, white
V = 2148.6 (3) Å30.5 × 0.3 × 0.22 mm
Z = 4
Data collection top
Stoe IPDS-2
diffractometer
3749 independent reflections
Radiation source: fine-focus sealed tube1919 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.134
Detector resolution: 6.67 pixels mm-1θmax = 25.0°, θmin = 1.7°
ω scansh = 1414
Absorption correction: integration
[Please provide reference]
k = 1817
Tmin = 0.985, Tmax = 0.997l = 2019
3749 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097 w = 1/[σ2(Fo2) + (0.0564P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.74(Δ/σ)max = 0.001
3749 reflectionsΔρmax = 0.16 e Å3
336 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0074 (7)
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
xyzUiso*/Ueq
H50.0127 (19)0.3042 (19)0.1359 (17)0.075 (7)*
H10.0628 (19)0.1301 (19)0.0978 (17)0.071 (8)*
C60.0047 (2)0.2747 (2)0.0714 (2)0.0689 (7)
C10.0361 (2)0.1725 (2)0.0496 (2)0.0734 (7)
H40.0652 (18)0.4108 (19)0.0147 (15)0.071 (7)*
C50.03802 (19)0.34094 (19)0.00111 (17)0.0582 (6)
C20.0232 (2)0.1372 (2)0.0430 (2)0.0683 (7)
H20.042 (2)0.067 (2)0.0580 (18)0.092 (9)*
C40.05173 (16)0.30604 (16)0.09562 (15)0.0489 (5)
O10.65053 (12)0.05881 (13)0.34780 (12)0.0707 (5)
C240.7103 (2)0.1513 (2)0.3804 (2)0.1013 (10)
H24A0.67940.18110.43460.152*
H24B0.78500.13230.39910.152*
H24C0.70690.20310.32950.152*
C30.02103 (18)0.20244 (18)0.11653 (19)0.0572 (6)
H130.5211 (16)0.2295 (17)0.3190 (14)0.061 (6)*
O20.53783 (12)0.12509 (12)0.34586 (12)0.0674 (5)
C200.53960 (17)0.06629 (18)0.33702 (15)0.0536 (5)
C70.09076 (17)0.38202 (16)0.17130 (15)0.0498 (5)
C210.48321 (19)0.16127 (18)0.32291 (15)0.0537 (5)
C190.48413 (18)0.02952 (16)0.33962 (15)0.0511 (5)
N30.06275 (15)0.48338 (14)0.17133 (14)0.0613 (5)
H110.3544 (18)0.3247 (17)0.2955 (14)0.061 (6)*
H30.0282 (18)0.1819 (18)0.1826 (17)0.071 (7)*
C230.5967 (3)0.1492 (2)0.43460 (19)0.1014 (10)
H23A0.55120.13820.48520.152*
H23B0.61980.22240.43480.152*
H23C0.65940.10360.44470.152*
C160.36937 (17)0.15981 (16)0.31175 (14)0.0478 (5)
C180.37016 (17)0.03017 (16)0.32955 (15)0.0522 (5)
C150.31216 (19)0.26058 (18)0.29182 (15)0.0491 (5)
N10.16380 (13)0.36252 (12)0.24991 (12)0.0477 (4)
O30.32370 (13)0.12827 (12)0.33480 (13)0.0768 (5)
N40.20982 (15)0.26099 (13)0.26938 (12)0.0539 (5)
C170.31287 (19)0.06452 (17)0.31658 (15)0.0509 (5)
N20.11850 (16)0.53090 (14)0.25169 (13)0.0616 (5)
H60.3131 (19)0.6067 (19)0.3406 (18)0.079 (8)*
H120.2336 (19)0.0668 (16)0.3085 (15)0.065 (6)*
C220.2071 (2)0.1333 (2)0.3299 (3)0.1030 (10)
H22A0.17550.10210.27060.155*
H22B0.18460.20650.33280.155*
H22C0.18310.09470.38310.155*
C80.17949 (17)0.45760 (16)0.29801 (15)0.0515 (5)
C140.3125 (2)0.5686 (2)0.3973 (2)0.0752 (7)
C90.24885 (18)0.47733 (17)0.38892 (15)0.0538 (6)
H70.411 (2)0.652 (2)0.484 (2)0.101 (11)*
C130.3717 (3)0.5933 (3)0.4831 (3)0.0924 (10)
C100.2459 (2)0.4127 (2)0.46811 (18)0.0649 (7)
H100.2006 (18)0.3528 (18)0.4615 (16)0.069 (7)*
C120.3681 (3)0.5295 (3)0.5613 (2)0.0958 (10)
C110.3040 (3)0.4389 (3)0.5537 (2)0.0878 (9)
H80.408 (3)0.550 (2)0.624 (2)0.124 (11)*
H90.306 (2)0.396 (2)0.611 (2)0.108 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C60.0733 (18)0.0710 (18)0.0596 (16)0.0172 (14)0.0058 (13)0.0050 (14)
C10.0648 (17)0.0756 (19)0.0760 (19)0.0078 (14)0.0096 (14)0.0131 (16)
C50.0580 (14)0.0523 (14)0.0631 (15)0.0109 (12)0.0018 (12)0.0105 (12)
C20.0642 (16)0.0608 (16)0.0796 (19)0.0060 (13)0.0062 (14)0.0001 (14)
C40.0406 (12)0.0482 (12)0.0572 (13)0.0089 (10)0.0029 (10)0.0075 (10)
O10.0390 (9)0.0704 (11)0.1027 (13)0.0079 (8)0.0072 (8)0.0052 (9)
C240.0481 (16)0.112 (2)0.142 (3)0.0030 (16)0.0004 (17)0.046 (2)
C30.0563 (14)0.0543 (14)0.0613 (15)0.0027 (11)0.0082 (12)0.0058 (12)
O20.0631 (10)0.0560 (9)0.0809 (11)0.0264 (8)0.0019 (9)0.0086 (8)
C200.0426 (13)0.0611 (14)0.0576 (13)0.0110 (11)0.0076 (11)0.0006 (11)
C70.0468 (13)0.0476 (13)0.0547 (13)0.0090 (10)0.0044 (11)0.0094 (10)
C210.0495 (14)0.0502 (14)0.0617 (14)0.0022 (11)0.0068 (11)0.0031 (11)
C190.0505 (13)0.0485 (13)0.0543 (13)0.0130 (11)0.0056 (10)0.0027 (10)
N30.0644 (12)0.0477 (11)0.0692 (12)0.0148 (9)0.0051 (10)0.0056 (9)
C230.139 (3)0.087 (2)0.0769 (19)0.053 (2)0.0040 (19)0.0137 (15)
C160.0495 (13)0.0462 (12)0.0479 (12)0.0106 (10)0.0056 (10)0.0045 (9)
C180.0502 (13)0.0445 (13)0.0615 (13)0.0043 (10)0.0042 (11)0.0006 (10)
C150.0510 (15)0.0480 (13)0.0487 (12)0.0056 (11)0.0071 (11)0.0054 (10)
N10.0489 (10)0.0382 (10)0.0552 (10)0.0105 (8)0.0021 (9)0.0065 (8)
O30.0543 (10)0.0468 (9)0.1277 (15)0.0004 (8)0.0029 (10)0.0060 (9)
N40.0531 (12)0.0424 (10)0.0639 (12)0.0108 (8)0.0036 (9)0.0070 (8)
C170.0419 (13)0.0503 (13)0.0593 (13)0.0068 (11)0.0003 (11)0.0039 (10)
N20.0700 (13)0.0471 (11)0.0658 (12)0.0133 (10)0.0019 (10)0.0024 (9)
C220.0546 (17)0.0726 (19)0.180 (3)0.0108 (14)0.0035 (19)0.0068 (19)
C80.0559 (13)0.0445 (13)0.0547 (12)0.0090 (10)0.0086 (11)0.0025 (10)
C140.091 (2)0.0685 (17)0.0661 (17)0.0008 (16)0.0092 (16)0.0054 (15)
C90.0576 (14)0.0468 (12)0.0573 (14)0.0104 (11)0.0082 (11)0.0037 (11)
C130.100 (2)0.086 (2)0.091 (3)0.0166 (19)0.007 (2)0.0272 (19)
C100.0756 (18)0.0616 (16)0.0569 (16)0.0105 (14)0.0046 (13)0.0029 (13)
C120.101 (2)0.112 (3)0.070 (2)0.014 (2)0.0122 (18)0.019 (2)
C110.113 (3)0.086 (2)0.0619 (19)0.021 (2)0.0001 (18)0.0022 (17)
Geometric parameters (Å, º) top
C6—C51.371 (3)C23—H23B0.9600
C6—C11.381 (4)C23—H23C0.9600
C6—H50.97 (2)C16—C171.388 (3)
C1—C21.361 (4)C16—C151.458 (3)
C1—H10.89 (2)C18—O31.361 (2)
C5—C41.385 (3)C18—C171.383 (3)
C5—H40.97 (2)C15—N41.267 (3)
C2—C31.379 (3)C15—H110.96 (2)
C2—H20.94 (3)N1—C81.371 (2)
C4—C31.392 (3)N1—N41.407 (2)
C4—C71.465 (3)O3—C221.434 (3)
O1—C201.363 (2)C17—H120.97 (2)
O1—C241.422 (3)N2—C81.313 (3)
C24—H24A0.9600C22—H22A0.9600
C24—H24B0.9600C22—H22B0.9600
C24—H24C0.9600C22—H22C0.9600
C3—H30.95 (2)C8—C91.474 (3)
O2—C191.367 (2)C14—C131.371 (4)
O2—C231.401 (3)C14—C91.385 (3)
C20—C211.382 (3)C14—H60.93 (2)
C20—C191.384 (3)C9—C101.375 (3)
C7—N31.316 (2)C13—C121.359 (5)
C7—N11.365 (2)C13—H70.88 (3)
C21—C161.396 (3)C10—C111.366 (4)
C21—H130.98 (2)C10—H100.93 (2)
C19—C181.398 (3)C12—C111.380 (5)
N3—N21.386 (3)C12—H80.99 (3)
C23—H23A0.9600C11—H90.96 (3)
C5—C6—C1119.5 (3)C17—C16—C21120.7 (2)
C5—C6—H5116.7 (14)C17—C16—C15121.3 (2)
C1—C6—H5123.9 (14)C21—C16—C15118.0 (2)
C2—C1—C6120.4 (3)O3—C18—C17124.7 (2)
C2—C1—H1121.3 (15)O3—C18—C19115.13 (19)
C6—C1—H1118.3 (15)C17—C18—C19120.2 (2)
C6—C5—C4120.8 (2)N4—C15—C16119.9 (2)
C6—C5—H4119.4 (13)N4—C15—H11122.2 (13)
C4—C5—H4119.5 (13)C16—C15—H11117.9 (13)
C1—C2—C3120.8 (3)C7—N1—C8106.55 (16)
C1—C2—H2120.8 (16)C7—N1—N4122.30 (17)
C3—C2—H2118.4 (16)C8—N1—N4131.14 (17)
C5—C4—C3119.2 (2)C18—O3—C22117.60 (18)
C5—C4—C7118.72 (19)C15—N4—N1114.92 (18)
C3—C4—C7121.97 (19)C18—C17—C16119.5 (2)
C20—O1—C24117.29 (18)C18—C17—H12122.3 (13)
O1—C24—H24A109.5C16—C17—H12118.2 (13)
O1—C24—H24B109.5C8—N2—N3107.85 (17)
H24A—C24—H24B109.5O3—C22—H22A109.5
O1—C24—H24C109.5O3—C22—H22B109.5
H24A—C24—H24C109.5H22A—C22—H22B109.5
H24B—C24—H24C109.5O3—C22—H22C109.5
C2—C3—C4119.4 (2)H22A—C22—H22C109.5
C2—C3—H3123.3 (14)H22B—C22—H22C109.5
C4—C3—H3117.2 (14)N2—C8—N1108.85 (19)
C19—O2—C23116.52 (18)N2—C8—C9123.77 (19)
O1—C20—C21124.0 (2)N1—C8—C9127.33 (18)
O1—C20—C19115.51 (19)C13—C14—C9120.2 (3)
C21—C20—C19120.5 (2)C13—C14—H6125.4 (16)
N3—C7—N1108.82 (19)C9—C14—H6114.3 (16)
N3—C7—C4124.16 (19)C10—C9—C14118.9 (2)
N1—C7—C4126.96 (18)C10—C9—C8122.1 (2)
C20—C21—C16119.3 (2)C14—C9—C8118.8 (2)
C20—C21—H13121.6 (12)C12—C13—C14120.7 (3)
C16—C21—H13119.1 (12)C12—C13—H7123.0 (19)
O2—C19—C20121.59 (19)C14—C13—H7116 (2)
O2—C19—C18118.5 (2)C11—C10—C9120.4 (3)
C20—C19—C18119.82 (19)C11—C10—H10122.0 (14)
C7—N3—N2107.92 (17)C9—C10—H10117.5 (14)
O2—C23—H23A109.5C13—C12—C11119.3 (3)
O2—C23—H23B109.5C13—C12—H8119.9 (18)
H23A—C23—H23B109.5C11—C12—H8120.7 (18)
O2—C23—H23C109.5C10—C11—C12120.5 (3)
H23A—C23—H23C109.5C10—C11—H9123.4 (18)
H23B—C23—H23C109.5C12—C11—H9116.1 (18)
C5—C6—C1—C21.0 (4)N3—C7—N1—C80.3 (2)
C1—C6—C5—C41.1 (4)C4—C7—N1—C8177.23 (19)
C6—C1—C2—C30.2 (4)N3—C7—N1—N4179.43 (17)
C6—C5—C4—C30.3 (3)C4—C7—N1—N41.9 (3)
C6—C5—C4—C7175.9 (2)C17—C18—O3—C222.3 (3)
C1—C2—C3—C40.6 (4)C19—C18—O3—C22176.8 (2)
C5—C4—C3—C20.6 (3)C16—C15—N4—N1178.80 (16)
C7—C4—C3—C2174.9 (2)C7—N1—N4—C15133.4 (2)
C24—O1—C20—C2123.3 (3)C8—N1—N4—C1545.5 (3)
C24—O1—C20—C19157.6 (2)O3—C18—C17—C16179.6 (2)
C5—C4—C7—N337.1 (3)C19—C18—C17—C161.3 (3)
C3—C4—C7—N3138.4 (2)C21—C16—C17—C182.0 (3)
C5—C4—C7—N1140.0 (2)C15—C16—C17—C18175.91 (19)
C3—C4—C7—N144.5 (3)C7—N3—N2—C80.5 (2)
O1—C20—C21—C16179.38 (19)N3—N2—C8—N10.6 (2)
C19—C20—C21—C160.3 (3)N3—N2—C8—C9178.38 (19)
C23—O2—C19—C2072.2 (3)C7—N1—C8—N20.5 (2)
C23—O2—C19—C18111.9 (3)N4—N1—C8—N2179.62 (18)
O1—C20—C19—O24.4 (3)C7—N1—C8—C9178.2 (2)
C21—C20—C19—O2174.8 (2)N4—N1—C8—C92.7 (3)
O1—C20—C19—C18179.78 (18)C13—C14—C9—C100.3 (4)
C21—C20—C19—C181.1 (3)C13—C14—C9—C8175.2 (2)
N1—C7—N3—N20.1 (2)N2—C8—C9—C10129.7 (2)
C4—C7—N3—N2177.69 (18)N1—C8—C9—C1047.7 (3)
C20—C21—C16—C171.3 (3)N2—C8—C9—C1445.0 (3)
C20—C21—C16—C15176.76 (19)N1—C8—C9—C14137.6 (2)
O2—C19—C18—O35.1 (3)C9—C14—C13—C120.6 (5)
C20—C19—C18—O3178.93 (19)C14—C9—C10—C110.6 (4)
O2—C19—C18—C17175.68 (19)C8—C9—C10—C11174.1 (2)
C20—C19—C18—C170.3 (3)C14—C13—C12—C110.0 (5)
C17—C16—C15—N46.8 (3)C9—C10—C11—C121.2 (4)
C21—C16—C15—N4171.2 (2)C13—C12—C11—C100.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H11···O2i0.96 (2)2.58 (2)3.156 (3)119.2 (15)
Symmetry code: (i) x+1, y1/2, z+1/2.
 

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