The title compound, C
22H
18Cl
2N
4, displays the characteristic features of 1,2,4-triazole derivatives. There is an N—H
N intermolecular hydrogen bond.
Supporting information
CCDC reference: 239269
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.010 Å
- R factor = 0.074
- wR factor = 0.133
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 35 Perc.
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.149
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.15
PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C5 .. 5.60 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C5 - C8 .. 5.12 su
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C13
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C2
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
7 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
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
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).
4-(2,4-Dichlorobenzylamino)-3-phenyl-5-
p-tolyl-4
H- 1,2,4-triazole
top
Crystal data top
C22H18Cl2N4 | Z = 2 |
Mr = 409.30 | F(000) = 424 |
Triclinic, P1 | Dx = 1.349 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.2604 (12) Å | Cell parameters from 4695 reflections |
b = 11.952 (3) Å | θ = 1.9–26.7° |
c = 14.775 (3) Å | µ = 0.34 mm−1 |
α = 113.152 (16)° | T = 293 K |
β = 91.984 (15)° | Plate, colourless |
γ = 95.864 (17)° | 0.18 × 0.14 × 0.07 mm |
V = 1007.8 (4) Å3 | |
Data collection top
Stoe IPDS-II diffractometer | 3654 independent reflections |
Radiation source: fine-focus sealed tube | 1272 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.149 |
w scans | θmax = 25.3°, θmin = 2.8° |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | h = −7→7 |
Tmin = 0.924, Tmax = 0.969 | k = −14→14 |
13341 measured reflections | l = −17→17 |
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)] = 0.074 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 0.93 | w = 1/[σ2(Fo2) + (0.0303P)2] where P = (Fo2 + 2Fc2)/3 |
3654 reflections | (Δ/σ)max < 0.001 |
253 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.15 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 | |
Cl1 | 0.0895 (3) | 0.80955 (16) | 0.26166 (12) | 0.0877 (6) | |
Cl2 | 0.3895 (3) | 1.21594 (18) | 0.57630 (12) | 0.1069 (7) | |
N3 | −0.0715 (7) | 0.9924 (5) | 0.1264 (3) | 0.0557 (13) | |
N1 | 0.1851 (7) | 0.8939 (5) | 0.0446 (4) | 0.0677 (15) | |
C8 | −0.0217 (9) | 0.8853 (7) | 0.0591 (4) | 0.0562 (16) | |
N2 | 0.2725 (7) | 1.0134 (5) | 0.1069 (4) | 0.0716 (16) | |
N4 | −0.2646 (6) | 1.0130 (4) | 0.1741 (3) | 0.0621 (14) | |
H4 | −0.3550 | 1.0579 | 0.1650 | 0.075* | |
C18 | 0.0516 (9) | 0.9574 (5) | 0.3420 (4) | 0.0587 (16) | |
C16 | −0.2936 (8) | 0.9500 (5) | 0.2403 (4) | 0.0658 (17) | |
H16A | −0.2755 | 0.8642 | 0.2057 | 0.079* | |
H16B | −0.4379 | 0.9545 | 0.2622 | 0.079* | |
C19 | 0.2096 (9) | 1.0186 (7) | 0.4171 (4) | 0.0678 (17) | |
H19 | 0.3290 | 0.9812 | 0.4235 | 0.081* | |
C22 | −0.1456 (10) | 1.1249 (7) | 0.3970 (5) | 0.0754 (19) | |
H22 | −0.2675 | 1.1609 | 0.3913 | 0.090* | |
C10 | 0.1437 (9) | 1.1996 (7) | 0.2276 (4) | 0.0686 (18) | |
C20 | 0.1903 (10) | 1.1356 (7) | 0.4829 (4) | 0.0726 (19) | |
C5 | −0.1631 (9) | 0.7704 (6) | 0.0066 (4) | 0.0566 (17) | |
C9 | 0.1167 (8) | 1.0736 (7) | 0.1565 (5) | 0.0591 (18) | |
C21 | 0.0086 (11) | 1.1909 (6) | 0.4742 (4) | 0.0795 (19) | |
H21 | −0.0080 | 1.2695 | 0.5188 | 0.095* | |
C7 | −0.4997 (9) | 0.6520 (7) | −0.0806 (4) | 0.0663 (18) | |
H7 | −0.6427 | 0.6505 | −0.1009 | 0.080* | |
C15 | −0.0157 (9) | 1.2761 (8) | 0.2390 (5) | 0.082 (2) | |
H15 | −0.1483 | 1.2464 | 0.2024 | 0.099* | |
C17 | −0.1287 (8) | 1.0097 (6) | 0.3287 (4) | 0.0577 (16) | |
C6 | −0.3802 (8) | 0.7627 (6) | −0.0262 (4) | 0.0649 (17) | |
H6 | −0.4437 | 0.8343 | −0.0107 | 0.078* | |
C4 | −0.0824 (10) | 0.6592 (7) | −0.0183 (5) | 0.077 (2) | |
H4A | 0.0592 | 0.6601 | 0.0035 | 0.093* | |
C2 | −0.4147 (11) | 0.5427 (7) | −0.1062 (4) | 0.0738 (18) | |
C11 | 0.3382 (9) | 1.2476 (8) | 0.2842 (5) | 0.085 (2) | |
H11 | 0.4466 | 1.1980 | 0.2778 | 0.102* | |
C3 | −0.1997 (12) | 0.5486 (8) | −0.0729 (5) | 0.089 (2) | |
H3 | −0.1368 | 0.4769 | −0.0882 | 0.107* | |
C13 | 0.2174 (14) | 1.4519 (9) | 0.3659 (6) | 0.127 (3) | |
H13 | 0.2408 | 1.5333 | 0.4109 | 0.153* | |
C14 | 0.0267 (14) | 1.3974 (8) | 0.3061 (6) | 0.111 (3) | |
H14 | −0.0818 | 1.4468 | 0.3117 | 0.133* | |
C1 | −0.5446 (12) | 0.4255 (7) | −0.1643 (5) | 0.118 (3) | |
H1A | −0.6908 | 0.4390 | −0.1737 | 0.177* | |
H1B | −0.5406 | 0.3721 | −0.1300 | 0.177* | |
H1C | −0.4878 | 0.3885 | −0.2273 | 0.177* | |
C12 | 0.3713 (13) | 1.3684 (9) | 0.3498 (6) | 0.114 (3) | |
H12 | 0.5042 | 1.3973 | 0.3862 | 0.137* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0873 (12) | 0.1008 (15) | 0.0744 (12) | 0.0316 (11) | 0.0025 (9) | 0.0301 (11) |
Cl2 | 0.0869 (13) | 0.1475 (19) | 0.0696 (12) | −0.0040 (12) | −0.0113 (10) | 0.0314 (12) |
N3 | 0.037 (3) | 0.091 (4) | 0.055 (3) | 0.020 (3) | 0.008 (2) | 0.042 (3) |
N1 | 0.030 (3) | 0.116 (5) | 0.079 (4) | 0.029 (3) | 0.018 (2) | 0.057 (3) |
C8 | 0.040 (4) | 0.088 (5) | 0.057 (4) | 0.009 (4) | 0.001 (3) | 0.046 (4) |
N2 | 0.038 (3) | 0.114 (5) | 0.078 (4) | 0.011 (3) | 0.007 (3) | 0.055 (4) |
N4 | 0.032 (2) | 0.110 (4) | 0.068 (3) | 0.031 (3) | 0.020 (2) | 0.054 (3) |
C18 | 0.052 (4) | 0.081 (5) | 0.051 (4) | 0.016 (3) | 0.010 (3) | 0.033 (3) |
C16 | 0.043 (3) | 0.114 (5) | 0.063 (4) | 0.016 (3) | 0.018 (3) | 0.057 (4) |
C19 | 0.050 (4) | 0.111 (6) | 0.056 (4) | 0.016 (4) | 0.009 (3) | 0.046 (4) |
C22 | 0.076 (5) | 0.100 (6) | 0.058 (4) | 0.029 (4) | 0.024 (4) | 0.034 (4) |
C10 | 0.056 (4) | 0.107 (6) | 0.051 (4) | 0.005 (4) | 0.009 (3) | 0.041 (4) |
C20 | 0.069 (4) | 0.108 (6) | 0.049 (4) | 0.013 (4) | 0.006 (3) | 0.040 (4) |
C5 | 0.050 (4) | 0.089 (5) | 0.060 (4) | 0.041 (4) | 0.026 (3) | 0.051 (4) |
C9 | 0.018 (3) | 0.116 (6) | 0.069 (4) | 0.007 (4) | −0.001 (3) | 0.066 (4) |
C21 | 0.096 (5) | 0.085 (5) | 0.057 (4) | 0.025 (4) | 0.014 (4) | 0.024 (4) |
C7 | 0.045 (4) | 0.092 (6) | 0.061 (4) | 0.015 (4) | 0.009 (3) | 0.028 (4) |
C15 | 0.052 (4) | 0.120 (7) | 0.099 (6) | 0.016 (5) | 0.000 (4) | 0.069 (5) |
C17 | 0.044 (3) | 0.097 (5) | 0.045 (4) | 0.009 (3) | 0.011 (3) | 0.041 (4) |
C6 | 0.045 (4) | 0.101 (6) | 0.069 (4) | 0.020 (4) | 0.013 (3) | 0.051 (4) |
C4 | 0.061 (4) | 0.109 (6) | 0.076 (5) | 0.024 (5) | 0.014 (4) | 0.048 (5) |
C2 | 0.084 (5) | 0.077 (6) | 0.060 (4) | 0.004 (5) | 0.009 (4) | 0.027 (4) |
C11 | 0.044 (4) | 0.133 (7) | 0.084 (5) | −0.002 (4) | −0.010 (4) | 0.056 (5) |
C3 | 0.091 (6) | 0.110 (7) | 0.084 (5) | 0.052 (5) | 0.027 (4) | 0.047 (5) |
C13 | 0.078 (6) | 0.191 (10) | 0.135 (8) | 0.024 (7) | 0.001 (6) | 0.086 (7) |
C14 | 0.121 (8) | 0.103 (7) | 0.121 (7) | 0.043 (6) | 0.038 (6) | 0.049 (6) |
C1 | 0.129 (7) | 0.117 (7) | 0.085 (5) | 0.007 (6) | 0.007 (5) | 0.020 (5) |
C12 | 0.080 (6) | 0.131 (8) | 0.107 (7) | −0.030 (6) | −0.019 (5) | 0.036 (6) |
Geometric parameters (Å, º) top
Cl1—C18 | 1.745 (6) | C5—C4 | 1.386 (7) |
Cl2—C20 | 1.725 (6) | C5—C6 | 1.409 (7) |
N3—C8 | 1.352 (6) | C21—H21 | 0.9300 |
N3—C9 | 1.385 (6) | C7—C6 | 1.370 (7) |
N3—N4 | 1.415 (5) | C7—C2 | 1.379 (7) |
N1—C8 | 1.320 (6) | C7—H7 | 0.9300 |
N1—N2 | 1.399 (6) | C15—C14 | 1.389 (9) |
C8—C5 | 1.461 (7) | C15—H15 | 0.9300 |
N2—C9 | 1.336 (6) | C6—H6 | 0.9300 |
N4—C16 | 1.456 (6) | C4—C3 | 1.364 (7) |
N4—H4 | 0.8600 | C4—H4A | 0.9300 |
C18—C19 | 1.373 (7) | C2—C3 | 1.402 (8) |
C18—C17 | 1.389 (7) | C2—C1 | 1.460 (8) |
C16—C17 | 1.519 (7) | C11—C12 | 1.375 (9) |
C16—H16A | 0.9700 | C11—H11 | 0.9300 |
C16—H16B | 0.9700 | C3—H3 | 0.9300 |
C19—C20 | 1.373 (8) | C13—C14 | 1.395 (9) |
C19—H19 | 0.9300 | C13—C12 | 1.417 (10) |
C22—C17 | 1.367 (7) | C13—H13 | 0.9300 |
C22—C21 | 1.384 (7) | C14—H14 | 0.9300 |
C22—H22 | 0.9300 | C1—H1A | 0.9600 |
C10—C11 | 1.386 (7) | C1—H1B | 0.9600 |
C10—C15 | 1.391 (8) | C1—H1C | 0.9600 |
C10—C9 | 1.447 (7) | C12—H12 | 0.9300 |
C20—C21 | 1.400 (7) | | |
| | | |
C8—N3—C9 | 107.2 (5) | C20—C21—H21 | 121.1 |
C8—N3—N4 | 127.2 (5) | C6—C7—C2 | 122.0 (5) |
C9—N3—N4 | 124.3 (5) | C6—C7—H7 | 119.0 |
C8—N1—N2 | 106.0 (5) | C2—C7—H7 | 119.0 |
N1—C8—N3 | 110.7 (6) | C14—C15—C10 | 118.8 (6) |
N1—C8—C5 | 120.8 (6) | C14—C15—H15 | 120.6 |
N3—C8—C5 | 128.6 (5) | C10—C15—H15 | 120.6 |
C9—N2—N1 | 109.2 (5) | C22—C17—C18 | 116.4 (5) |
N3—N4—C16 | 112.7 (4) | C22—C17—C16 | 119.8 (5) |
N3—N4—H4 | 123.7 | C18—C17—C16 | 123.6 (6) |
C16—N4—H4 | 123.7 | C7—C6—C5 | 121.4 (6) |
C19—C18—C17 | 122.4 (6) | C7—C6—H6 | 119.3 |
C19—C18—Cl1 | 116.6 (5) | C5—C6—H6 | 119.3 |
C17—C18—Cl1 | 121.0 (5) | C3—C4—C5 | 123.5 (6) |
N4—C16—C17 | 109.3 (5) | C3—C4—H4A | 118.3 |
N4—C16—H16A | 109.8 | C5—C4—H4A | 118.3 |
C17—C16—H16A | 109.8 | C7—C2—C3 | 117.3 (6) |
N4—C16—H16B | 109.8 | C7—C2—C1 | 121.3 (6) |
C17—C16—H16B | 109.8 | C3—C2—C1 | 121.5 (7) |
H16A—C16—H16B | 108.3 | C12—C11—C10 | 120.2 (7) |
C18—C19—C20 | 119.6 (5) | C12—C11—H11 | 119.9 |
C18—C19—H19 | 120.2 | C10—C11—H11 | 119.9 |
C20—C19—H19 | 120.2 | C4—C3—C2 | 120.3 (6) |
C17—C22—C21 | 123.6 (6) | C4—C3—H3 | 119.9 |
C17—C22—H22 | 118.2 | C2—C3—H3 | 119.9 |
C21—C22—H22 | 118.2 | C14—C13—C12 | 111.8 (9) |
C11—C10—C15 | 118.6 (7) | C14—C13—H13 | 124.1 |
C11—C10—C9 | 118.9 (6) | C12—C13—H13 | 124.1 |
C15—C10—C9 | 122.5 (6) | C15—C14—C13 | 125.9 (8) |
C19—C20—C21 | 120.1 (6) | C15—C14—H14 | 117.0 |
C19—C20—Cl2 | 120.6 (5) | C13—C14—H14 | 117.0 |
C21—C20—Cl2 | 119.4 (6) | C2—C1—H1A | 109.5 |
C4—C5—C6 | 115.5 (6) | C2—C1—H1B | 109.5 |
C4—C5—C8 | 119.9 (5) | H1A—C1—H1B | 109.5 |
C6—C5—C8 | 124.5 (5) | C2—C1—H1C | 109.5 |
N2—C9—N3 | 106.8 (6) | H1A—C1—H1C | 109.5 |
N2—C9—C10 | 125.7 (6) | H1B—C1—H1C | 109.5 |
N3—C9—C10 | 127.5 (5) | C11—C12—C13 | 124.7 (8) |
C22—C21—C20 | 117.8 (6) | C11—C12—H12 | 117.7 |
C22—C21—H21 | 121.1 | C13—C12—H12 | 117.7 |
| | | |
N2—N1—C8—N3 | 0.5 (6) | C19—C20—C21—C22 | −1.1 (9) |
N2—N1—C8—C5 | −178.8 (4) | Cl2—C20—C21—C22 | 178.5 (5) |
C9—N3—C8—N1 | −0.4 (6) | C11—C10—C15—C14 | 0.4 (10) |
N4—N3—C8—N1 | −167.8 (4) | C9—C10—C15—C14 | −177.3 (6) |
C9—N3—C8—C5 | 178.8 (5) | C21—C22—C17—C18 | 2.3 (9) |
N4—N3—C8—C5 | 11.3 (8) | C21—C22—C17—C16 | −173.3 (5) |
C8—N1—N2—C9 | −0.4 (6) | C19—C18—C17—C22 | −2.3 (8) |
C8—N3—N4—C16 | 66.5 (6) | Cl1—C18—C17—C22 | 178.6 (4) |
C9—N3—N4—C16 | −99.0 (6) | C19—C18—C17—C16 | 173.2 (5) |
N3—N4—C16—C17 | 69.5 (6) | Cl1—C18—C17—C16 | −6.0 (8) |
C17—C18—C19—C20 | 0.6 (9) | N4—C16—C17—C22 | 69.8 (6) |
Cl1—C18—C19—C20 | 179.8 (5) | N4—C16—C17—C18 | −105.5 (6) |
C18—C19—C20—C21 | 1.1 (9) | C2—C7—C6—C5 | −0.1 (9) |
C18—C19—C20—Cl2 | −178.5 (4) | C4—C5—C6—C7 | −1.1 (8) |
N1—C8—C5—C4 | 32.0 (7) | C8—C5—C6—C7 | 175.7 (5) |
N3—C8—C5—C4 | −147.1 (5) | C6—C5—C4—C3 | 1.6 (8) |
N1—C8—C5—C6 | −144.8 (5) | C8—C5—C4—C3 | −175.4 (6) |
N3—C8—C5—C6 | 36.1 (8) | C6—C7—C2—C3 | 0.9 (9) |
N1—N2—C9—N3 | 0.2 (6) | C6—C7—C2—C1 | −179.9 (6) |
N1—N2—C9—C10 | −179.6 (5) | C15—C10—C11—C12 | −0.2 (10) |
C8—N3—C9—N2 | 0.1 (5) | C9—C10—C11—C12 | 177.6 (7) |
N4—N3—C9—N2 | 168.0 (4) | C5—C4—C3—C2 | −0.9 (10) |
C8—N3—C9—C10 | 179.9 (5) | C7—C2—C3—C4 | −0.5 (9) |
N4—N3—C9—C10 | −12.2 (8) | C1—C2—C3—C4 | −179.6 (6) |
C11—C10—C9—N2 | −31.7 (8) | C10—C15—C14—C13 | −0.8 (12) |
C15—C10—C9—N2 | 146.0 (6) | C12—C13—C14—C15 | 0.9 (12) |
C11—C10—C9—N3 | 148.5 (5) | C10—C11—C12—C13 | 0.3 (13) |
C15—C10—C9—N3 | −33.7 (9) | C14—C13—C12—C11 | −0.6 (13) |
C17—C22—C21—C20 | −0.7 (10) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···N2i | 0.86 | 2.39 | 3.031 (6) | 132 |
Symmetry code: (i) x−1, y, z. |