1-[4-(4-Methyl­pyrimidin-2-yl)piperazin-1-ylmeth­yl]-1H-benzotriazole

The title compound, C₁₆H₁₉N₇, is a potent new herbicide. X-ray analysis reveals that the piperazine ring adopts a chair conformation and weak C—H...N hydrogen bonds link the mol­ecules into a chain along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.048
• wR factor = 0.135
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); 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, 1999); software used to prepare material for publication: SHELXTL.

1-[4-(4-Methylpyrimidin-2-yl)piperazin-1-ylmethyl]-1H-benzotriazole

Crystal data

C16H19N7	Z = 2
Mr = 309.38	F(000) = 328
Triclinic, P1	Dx = 1.334 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5207 (17) Å	Cell parameters from 1635 reflections
b = 9.2488 (16) Å	θ = 2.3–26.2°
c = 13.429 (4) Å	µ = 0.09 mm^−1
α = 102.108 (8)°	T = 294 K
β = 94.112 (7)°	Prism, colourless
γ = 101.504 (8)°	0.26 × 0.24 × 0.20 mm
V = 770.5 (3) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3104 independent reflections
Radiation source: fine-focus sealed tube	2102 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 26.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.972, Tmax = 0.983	k = −11→11
4365 measured reflections	l = −16→7

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0614P)^2 + 0.1903P] where P = (Fo^2 + 2Fc^2)/3
3104 reflections	(Δ/σ)max = 0.001
209 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.0256 (2)	0.16368 (18)	0.08980 (12)	0.0448 (4)
N2	−0.1810 (3)	0.1463 (2)	0.10249 (14)	0.0596 (5)
N3	−0.2741 (3)	0.2019 (2)	0.03535 (14)	0.0624 (5)
N4	0.2611 (2)	0.23005 (17)	0.25140 (11)	0.0396 (4)
N5	0.3795 (3)	0.51160 (17)	0.39374 (11)	0.0416 (4)
N6	0.4797 (3)	0.74315 (18)	0.35356 (12)	0.0488 (4)
N7	0.1601 (3)	0.6799 (2)	0.42649 (14)	0.0583 (5)
C1	0.0669 (3)	0.2329 (2)	0.01128 (13)	0.0409 (4)
C2	−0.1273 (3)	0.2571 (2)	−0.02272 (14)	0.0465 (5)
C3	−0.1475 (4)	0.3256 (3)	−0.10485 (16)	0.0598 (6)
H3	−0.2763	0.3430	−0.1280	0.072*
C4	0.0276 (4)	0.3657 (3)	−0.14938 (18)	0.0676 (7)
H4	0.0191	0.4120	−0.2042	0.081*
C5	0.2217 (4)	0.3394 (3)	−0.11507 (18)	0.0683 (7)
H5	0.3382	0.3682	−0.1483	0.082*
C6	0.2461 (3)	0.2730 (3)	−0.03465 (16)	0.0544 (6)
H6	0.3754	0.2559	−0.0121	0.065*
C7	0.1670 (3)	0.1167 (2)	0.16130 (14)	0.0475 (5)
H7A	0.0879	0.0298	0.1823	0.057*
H7B	0.2787	0.0838	0.1247	0.057*
C8	0.1087 (3)	0.2894 (2)	0.31321 (14)	0.0426 (5)
H8A	0.0066	0.2060	0.3266	0.051*
H8B	0.0338	0.3461	0.2759	0.051*
C9	0.2186 (3)	0.3908 (2)	0.41291 (14)	0.0444 (5)
H9A	0.1170	0.4339	0.4520	0.053*
H9B	0.2829	0.3321	0.4529	0.053*
C10	0.5331 (3)	0.4520 (2)	0.33370 (14)	0.0440 (5)
H10A	0.6055	0.3946	0.3714	0.053*
H10B	0.6370	0.5350	0.3211	0.053*
C11	0.4240 (3)	0.3514 (2)	0.23333 (14)	0.0428 (5)
H11A	0.3610	0.4109	0.1934	0.051*
H11B	0.5260	0.3084	0.1946	0.051*
C12	0.3364 (3)	0.6498 (2)	0.39045 (13)	0.0424 (5)
C13	0.4403 (4)	0.8812 (2)	0.35349 (16)	0.0536 (5)
C14	0.2630 (4)	0.9204 (3)	0.38875 (19)	0.0661 (7)
H14	0.2360	1.0154	0.3885	0.079*
C15	0.1277 (4)	0.8168 (3)	0.42415 (19)	0.0696 (7)
H15	0.0064	0.8426	0.4480	0.084*
C16	0.5980 (4)	0.9835 (3)	0.3114 (2)	0.0813 (8)
H16A	0.7356	0.9659	0.3271	0.122*
H16B	0.5962	1.0870	0.3415	0.122*
H16C	0.5645	0.9641	0.2384	0.122*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0422 (10)	0.0491 (10)	0.0396 (9)	0.0098 (7)	0.0015 (7)	0.0037 (7)
N2	0.0438 (11)	0.0734 (13)	0.0550 (11)	0.0049 (9)	0.0067 (8)	0.0078 (9)
N3	0.0420 (10)	0.0844 (14)	0.0569 (11)	0.0155 (10)	0.0020 (9)	0.0074 (10)
N4	0.0451 (9)	0.0355 (8)	0.0368 (8)	0.0081 (7)	0.0034 (7)	0.0062 (6)
N5	0.0502 (10)	0.0346 (8)	0.0389 (8)	0.0060 (7)	0.0082 (7)	0.0086 (7)
N6	0.0522 (10)	0.0437 (10)	0.0498 (9)	0.0036 (8)	0.0033 (8)	0.0163 (8)
N7	0.0666 (13)	0.0545 (11)	0.0616 (11)	0.0218 (10)	0.0229 (9)	0.0174 (9)
C1	0.0408 (11)	0.0429 (10)	0.0352 (9)	0.0118 (8)	−0.0011 (8)	0.0002 (8)
C2	0.0396 (11)	0.0534 (12)	0.0410 (10)	0.0140 (9)	−0.0019 (8)	−0.0027 (9)
C3	0.0562 (14)	0.0708 (15)	0.0522 (12)	0.0268 (12)	−0.0096 (11)	0.0070 (11)
C4	0.0748 (17)	0.0808 (17)	0.0534 (13)	0.0237 (14)	−0.0017 (12)	0.0260 (12)
C5	0.0585 (15)	0.0934 (19)	0.0591 (14)	0.0152 (13)	0.0109 (11)	0.0310 (13)
C6	0.0411 (12)	0.0763 (15)	0.0499 (12)	0.0193 (11)	0.0057 (9)	0.0172 (11)
C7	0.0584 (13)	0.0406 (11)	0.0415 (10)	0.0133 (10)	0.0002 (9)	0.0047 (8)
C8	0.0461 (11)	0.0390 (10)	0.0420 (10)	0.0050 (9)	0.0086 (8)	0.0111 (8)
C9	0.0550 (12)	0.0391 (10)	0.0396 (10)	0.0066 (9)	0.0145 (9)	0.0106 (8)
C10	0.0417 (11)	0.0439 (11)	0.0453 (10)	0.0065 (9)	0.0046 (8)	0.0109 (9)
C11	0.0447 (11)	0.0468 (11)	0.0395 (10)	0.0130 (9)	0.0107 (8)	0.0106 (8)
C12	0.0524 (12)	0.0406 (11)	0.0313 (9)	0.0044 (9)	0.0008 (8)	0.0085 (8)
C13	0.0617 (14)	0.0448 (12)	0.0513 (12)	0.0029 (10)	−0.0011 (10)	0.0156 (10)
C14	0.0810 (18)	0.0520 (14)	0.0736 (16)	0.0243 (13)	0.0162 (13)	0.0211 (12)
C15	0.0791 (17)	0.0641 (16)	0.0769 (16)	0.0316 (14)	0.0271 (14)	0.0198 (13)
C16	0.0808 (19)	0.0605 (16)	0.110 (2)	0.0069 (14)	0.0187 (16)	0.0424 (16)

Geometric parameters (Å, º)

N1—N2	1.352 (2)	C5—H5	0.93
N1—C1	1.360 (2)	C6—H6	0.93
N1—C7	1.473 (2)	C7—H7A	0.97
N2—N3	1.298 (3)	C7—H7B	0.97
N3—C2	1.365 (3)	C8—C9	1.501 (3)
N4—C7	1.430 (2)	C8—H8A	0.97
N4—C8	1.457 (2)	C8—H8B	0.97
N4—C11	1.457 (2)	C9—H9A	0.97
N5—C12	1.370 (2)	C9—H9B	0.97
N5—C9	1.451 (2)	C10—C11	1.504 (3)
N5—C10	1.452 (2)	C10—H10A	0.97
N6—C12	1.337 (2)	C10—H10B	0.97
N6—C13	1.352 (3)	C11—H11A	0.97
N7—C15	1.330 (3)	C11—H11B	0.97
N7—C12	1.336 (3)	C13—C14	1.366 (3)
C1—C6	1.382 (3)	C13—C16	1.481 (3)
C1—C2	1.391 (3)	C14—C15	1.356 (3)
C2—C3	1.393 (3)	C14—H14	0.93
C3—C4	1.349 (3)	C15—H15	0.93
C3—H3	0.93	C16—H16A	0.96
C4—C5	1.400 (3)	C16—H16B	0.96
C4—H4	0.93	C16—H16C	0.96
C5—C6	1.364 (3)
N2—N1—C1	109.99 (16)	N4—C8—H8B	109.6
N2—N1—C7	119.05 (16)	C9—C8—H8B	109.6
C1—N1—C7	130.86 (16)	H8A—C8—H8B	108.1
N3—N2—N1	109.01 (17)	N5—C9—C8	110.09 (14)
N2—N3—C2	108.31 (17)	N5—C9—H9A	109.6
C7—N4—C8	113.74 (15)	C8—C9—H9A	109.6
C7—N4—C11	114.47 (15)	N5—C9—H9B	109.6
C8—N4—C11	111.63 (14)	C8—C9—H9B	109.6
C12—N5—C9	120.77 (16)	H9A—C9—H9B	108.2
C12—N5—C10	121.44 (15)	N5—C10—C11	109.74 (15)
C9—N5—C10	111.52 (15)	N5—C10—H10A	109.7
C12—N6—C13	116.02 (18)	C11—C10—H10A	109.7
C15—N7—C12	115.34 (19)	N5—C10—H10B	109.7
N1—C1—C6	133.72 (18)	C11—C10—H10B	109.7
N1—C1—C2	103.99 (17)	H10A—C10—H10B	108.2
C6—C1—C2	122.27 (18)	N4—C11—C10	110.20 (14)
N3—C2—C1	108.69 (18)	N4—C11—H11A	109.6
N3—C2—C3	130.69 (19)	C10—C11—H11A	109.6
C1—C2—C3	120.61 (19)	N4—C11—H11B	109.6
C4—C3—C2	117.2 (2)	C10—C11—H11B	109.6
C4—C3—H3	121.4	H11A—C11—H11B	108.1
C2—C3—H3	121.4	N7—C12—N6	126.34 (19)
C3—C4—C5	121.6 (2)	N7—C12—N5	117.49 (17)
C3—C4—H4	119.2	N6—C12—N5	116.15 (18)
C5—C4—H4	119.2	N6—C13—C14	121.1 (2)
C6—C5—C4	122.4 (2)	N6—C13—C16	115.8 (2)
C6—C5—H5	118.8	C14—C13—C16	123.0 (2)
C4—C5—H5	118.8	C15—C14—C13	118.0 (2)
C5—C6—C1	115.9 (2)	C15—C14—H14	121.0
C5—C6—H6	122.1	C13—C14—H14	121.0
C1—C6—H6	122.1	N7—C15—C14	123.2 (2)
N4—C7—N1	115.55 (15)	N7—C15—H15	118.4
N4—C7—H7A	108.4	C14—C15—H15	118.4
N1—C7—H7A	108.4	C13—C16—H16A	109.5
N4—C7—H7B	108.4	C13—C16—H16B	109.5
N1—C7—H7B	108.4	H16A—C16—H16B	109.5
H7A—C7—H7B	107.5	C13—C16—H16C	109.5
N4—C8—C9	110.24 (16)	H16A—C16—H16C	109.5
N4—C8—H8A	109.6	H16B—C16—H16C	109.5
C9—C8—H8A	109.6
C1—N1—N2—N3	−0.1 (2)	C7—N4—C8—C9	172.07 (15)
C7—N1—N2—N3	176.62 (17)	C11—N4—C8—C9	−56.53 (19)
N1—N2—N3—C2	−0.1 (2)	C12—N5—C9—C8	94.3 (2)
N2—N1—C1—C6	−177.9 (2)	C10—N5—C9—C8	−58.2 (2)
C7—N1—C1—C6	5.8 (4)	N4—C8—C9—N5	56.3 (2)
N2—N1—C1—C2	0.3 (2)	C12—N5—C10—C11	−94.0 (2)
C7—N1—C1—C2	−175.98 (18)	C9—N5—C10—C11	58.37 (19)
N2—N3—C2—C1	0.2 (2)	C7—N4—C11—C10	−172.10 (15)
N2—N3—C2—C3	179.1 (2)	C8—N4—C11—C10	56.88 (19)
N1—C1—C2—N3	−0.3 (2)	N5—C10—C11—N4	−56.9 (2)
C6—C1—C2—N3	178.17 (18)	C15—N7—C12—N6	0.3 (3)
N1—C1—C2—C3	−179.27 (18)	C15—N7—C12—N5	178.34 (19)
C6—C1—C2—C3	−0.8 (3)	C13—N6—C12—N7	0.2 (3)
N3—C2—C3—C4	−178.3 (2)	C13—N6—C12—N5	−177.93 (16)
C1—C2—C3—C4	0.4 (3)	C9—N5—C12—N7	13.9 (3)
C2—C3—C4—C5	0.2 (4)	C10—N5—C12—N7	163.73 (17)
C3—C4—C5—C6	−0.5 (4)	C9—N5—C12—N6	−167.80 (15)
C4—C5—C6—C1	0.1 (4)	C10—N5—C12—N6	−18.0 (3)
N1—C1—C6—C5	178.5 (2)	C12—N6—C13—C14	−0.4 (3)
C2—C1—C6—C5	0.6 (3)	C12—N6—C13—C16	−179.30 (19)
C8—N4—C7—N1	58.0 (2)	N6—C13—C14—C15	0.2 (4)
C11—N4—C7—N1	−72.0 (2)	C16—C13—C14—C15	179.0 (2)
N2—N1—C7—N4	−88.9 (2)	C12—N7—C15—C14	−0.5 (4)
C1—N1—C7—N4	87.1 (2)	C13—C14—C15—N7	0.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···N3^i	0.93	2.50	3.430 (3)	176
C9—H9A···N7	0.97	2.34	2.746 (3)	105
C10—H10B···N6	0.97	2.33	2.744 (3)	105

Symmetry code: (i) x+1, y, z.