N-[2-({[1-(4-Chloro-phen-yl)-1H-pyrazol-3-yl]-oxy}meth-yl)phen-yl]-N-meth-oxy-hydrazinecarboxamide.

In the title compound, C(18)H(18)ClN(5)O(3), the hydrazinecarboxamide N-N-C(O)-N unit is nearly planar [maximum deviation = 0.074 (2) Å] and is inclined at a dihedral angle of 57.43 (7)° with respect to the plane of the attached benzene ring. The chloro-phenyl group makes dihedral angles of 19.71 (7) and 34.07 (6)° with the pyrazole and benzene rings, respectively. In the crystal, pairs of N-H⋯O hydrogen bonds link the mol-ecules into inversion dimers that are further linked into chains along the a-axis direction by N-H⋯N hydrogen bonds. In addition, π-π stacking inter-actions are observed between benzene rings [centroid-centroid distance = 3.680 (1) Å].

Related literature

For the biological activity of pyraclostrobin (systematic name: methyl N-{2-[1-(4-chloro­phen­yl)-1H-pyrazol-3-yloxymeth­yl]phen­yl}), see: Esteve-Turrillas et al. (2011 ▶); Mercader et al. (2008 ▶); Patel et al. (2012 ▶). For a related structure, see: Attia et al. (2012 ▶).

Experimental

Crystal data

C18H18ClN5O3

M = 387.82

Monoclinic,

a = 7.6830 (4) Å

b = 9.1597 (4) Å

c = 26.1083 (12) Å

β = 91.683 (4)°

V = 1836.55 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.832, T max = 1.000

27359 measured reflections

3616 independent reflections

2922 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.112

S = 1.12

3616 reflections

256 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812038214/gk2517sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038214/gk2517Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812038214/gk2517Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H18ClN5O3	F(000) = 808
Mr = 387.82	Dx = 1.403 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 14322 reflections
a = 7.6830 (4) Å	θ = 3.5–28.0°
b = 9.1597 (4) Å	µ = 0.24 mm−1
c = 26.1083 (12) Å	T = 293 K
β = 91.683 (4)°	Plate, colourless
V = 1836.55 (15) Å3	0.3 × 0.2 × 0.2 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3616 independent reflections
Radiation source: fine-focus sealed tube	2922 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.5°
ω scan	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −11→11
Tmin = 0.832, Tmax = 1.000	l = −32→32
27359 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0328P)2 + 1.1459P] where P = (Fo2 + 2Fc2)/3
3616 reflections	(Δ/σ)max < 0.001
256 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Cl1	0.85943 (10)	0.62565 (8)	0.12909 (3)	0.0738 (2)
C1	0.2793 (3)	−0.0901 (2)	−0.06670 (7)	0.0343 (4)
O1	0.43612 (17)	−0.10159 (17)	−0.05818 (5)	0.0413 (4)
N2	0.2112 (2)	−0.0929 (2)	−0.11646 (6)	0.0417 (4)
O3	0.03330 (18)	−0.13060 (17)	−0.12029 (6)	0.0459 (4)
C4	−0.0602 (3)	−0.0201 (4)	−0.14807 (11)	0.0706 (8)
H4B	−0.1812	−0.0459	−0.1506	0.106*
H4A	−0.0148	−0.0116	−0.1818	0.106*
H4C	−0.0474	0.0714	−0.1305	0.106*
N5	0.1626 (2)	−0.0688 (2)	−0.03072 (6)	0.0394 (4)
N6	0.2138 (2)	−0.0411 (2)	0.02087 (7)	0.0408 (4)
C7	0.3083 (3)	−0.1280 (2)	−0.16026 (8)	0.0404 (5)
C8	0.2614 (3)	−0.2474 (3)	−0.19022 (9)	0.0556 (6)
H8	0.1703	−0.3074	−0.1806	0.067*
C9	0.3496 (4)	−0.2774 (3)	−0.23418 (10)	0.0668 (8)
H9	0.3177	−0.3571	−0.2544	0.080*
C10	0.4843 (4)	−0.1895 (4)	−0.24800 (9)	0.0648 (8)
H10	0.5456	−0.2110	−0.2772	0.078*
C11	0.5297 (3)	−0.0690 (3)	−0.21873 (8)	0.0534 (6)
H11	0.6205	−0.0094	−0.2289	0.064*
C12	0.4424 (3)	−0.0350 (3)	−0.17444 (7)	0.0409 (5)
C13	0.4906 (3)	0.0949 (3)	−0.14239 (8)	0.0453 (5)
H131	0.3875	0.1335	−0.1266	0.054*
H132	0.5729	0.0662	−0.1154	0.054*
O13	0.5663 (2)	0.2046 (2)	−0.17350 (6)	0.0566 (4)
C14	0.6187 (3)	0.3245 (3)	−0.14708 (9)	0.0480 (6)
N15	0.6511 (2)	0.3234 (2)	−0.09724 (7)	0.0454 (4)
N16	0.7001 (2)	0.4639 (2)	−0.08603 (7)	0.0464 (5)
C17	0.6965 (4)	0.5466 (3)	−0.12880 (11)	0.0653 (7)
H17	0.7243	0.6453	−0.1305	0.078*
C18	0.6457 (4)	0.4619 (3)	−0.16864 (11)	0.0636 (7)
H18	0.6318	0.4889	−0.2029	0.076*
C19	0.7379 (3)	0.5041 (2)	−0.03455 (9)	0.0425 (5)
C20	0.6784 (3)	0.4182 (2)	0.00479 (9)	0.0425 (5)
H20	0.6131	0.3349	−0.0027	0.051*
C21	0.7157 (3)	0.4559 (2)	0.05512 (9)	0.0464 (5)
H21	0.6777	0.3975	0.0817	0.056*
C22	0.8103 (3)	0.5816 (3)	0.06560 (10)	0.0504 (6)
C23	0.8675 (3)	0.6674 (3)	0.02681 (11)	0.0584 (7)
H23	0.9305	0.7517	0.0344	0.070*
C24	0.8325 (3)	0.6298 (3)	−0.02355 (11)	0.0548 (6)
H24	0.8720	0.6882	−0.0499	0.066*
H61	0.305 (3)	0.013 (3)	0.0208 (8)	0.045 (7)*
H62	0.251 (3)	−0.123 (3)	0.0344 (10)	0.053 (7)*
H51	0.053 (3)	−0.051 (3)	−0.0385 (9)	0.051 (7)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0739 (5)	0.0668 (5)	0.0798 (5)	−0.0013 (4)	−0.0113 (4)	−0.0195 (4)
C1	0.0345 (11)	0.0338 (10)	0.0345 (10)	−0.0024 (8)	0.0004 (8)	0.0022 (8)
O1	0.0298 (7)	0.0558 (9)	0.0381 (8)	0.0005 (7)	−0.0013 (6)	0.0025 (7)
N2	0.0273 (8)	0.0621 (12)	0.0357 (9)	−0.0054 (8)	−0.0017 (7)	−0.0022 (8)
O3	0.0298 (7)	0.0595 (10)	0.0481 (9)	−0.0076 (7)	−0.0048 (6)	0.0012 (7)
C4	0.0473 (15)	0.100 (2)	0.0640 (17)	0.0128 (15)	−0.0123 (12)	0.0124 (16)
N5	0.0324 (9)	0.0516 (11)	0.0342 (9)	0.0018 (8)	−0.0015 (7)	−0.0015 (8)
N6	0.0385 (10)	0.0487 (12)	0.0350 (10)	−0.0009 (10)	−0.0010 (8)	−0.0004 (9)
C7	0.0348 (11)	0.0544 (13)	0.0315 (10)	0.0046 (10)	−0.0055 (8)	−0.0015 (9)
C8	0.0558 (15)	0.0615 (16)	0.0491 (14)	−0.0044 (12)	−0.0036 (11)	−0.0096 (12)
C9	0.0723 (18)	0.0781 (19)	0.0495 (15)	0.0057 (16)	−0.0056 (13)	−0.0237 (14)
C10	0.0602 (16)	0.097 (2)	0.0370 (13)	0.0140 (16)	0.0012 (11)	−0.0177 (14)
C11	0.0413 (12)	0.0837 (19)	0.0352 (11)	0.0048 (12)	−0.0002 (9)	−0.0012 (12)
C12	0.0325 (10)	0.0583 (13)	0.0315 (10)	0.0065 (10)	−0.0032 (8)	−0.0008 (10)
C13	0.0417 (12)	0.0565 (14)	0.0379 (11)	−0.0034 (10)	0.0058 (9)	0.0032 (10)
O13	0.0651 (11)	0.0650 (11)	0.0401 (9)	−0.0129 (9)	0.0058 (8)	0.0076 (8)
C14	0.0415 (12)	0.0543 (14)	0.0486 (13)	0.0016 (10)	0.0084 (10)	0.0117 (11)
N15	0.0462 (11)	0.0394 (10)	0.0509 (11)	−0.0045 (8)	0.0033 (8)	0.0064 (8)
N16	0.0448 (11)	0.0346 (10)	0.0603 (12)	0.0004 (8)	0.0084 (9)	0.0097 (9)
C17	0.0774 (19)	0.0471 (15)	0.0722 (18)	−0.0012 (13)	0.0139 (15)	0.0197 (14)
C18	0.0702 (17)	0.0653 (17)	0.0558 (16)	0.0017 (14)	0.0075 (13)	0.0215 (14)
C19	0.0344 (11)	0.0321 (11)	0.0612 (14)	0.0038 (9)	0.0066 (10)	0.0039 (10)
C20	0.0354 (11)	0.0301 (10)	0.0623 (14)	0.0002 (9)	0.0062 (10)	−0.0001 (10)
C21	0.0397 (12)	0.0377 (12)	0.0622 (15)	0.0043 (10)	0.0054 (10)	0.0019 (11)
C22	0.0400 (12)	0.0404 (12)	0.0708 (16)	0.0064 (10)	0.0005 (11)	−0.0076 (12)
C23	0.0481 (14)	0.0370 (13)	0.090 (2)	−0.0070 (11)	0.0034 (13)	−0.0050 (13)
C24	0.0499 (14)	0.0357 (12)	0.0793 (18)	−0.0051 (11)	0.0109 (12)	0.0061 (12)

Cl1—C22	1.737 (3)	C12—C13	1.495 (3)
C1—O1	1.223 (2)	C13—O13	1.427 (3)
C1—N5	1.332 (3)	C13—H131	0.9700
C1—N2	1.387 (2)	C13—H132	0.9700
N2—O3	1.411 (2)	O13—C14	1.352 (3)
N2—C7	1.420 (3)	C14—N15	1.318 (3)
O3—C4	1.427 (3)	C14—C18	1.397 (3)
C4—H4B	0.9600	N15—N16	1.370 (3)
C4—H4A	0.9600	N16—C17	1.349 (3)
C4—H4C	0.9600	N16—C19	1.415 (3)
N5—N6	1.415 (2)	C17—C18	1.346 (4)
N5—H51	0.88 (2)	C17—H17	0.9300
N6—H61	0.86 (2)	C18—H18	0.9300
N6—H62	0.87 (3)	C19—C20	1.382 (3)
C7—C8	1.386 (3)	C19—C24	1.387 (3)
C7—C12	1.395 (3)	C20—C21	1.380 (3)
C8—C9	1.378 (4)	C20—H20	0.9300
C8—H8	0.9300	C21—C22	1.385 (3)
C9—C10	1.368 (4)	C21—H21	0.9300
C9—H9	0.9300	C22—C23	1.364 (4)
C10—C11	1.382 (4)	C23—C24	1.378 (4)
C10—H10	0.9300	C23—H23	0.9300
C11—C12	1.389 (3)	C24—H24	0.9300
C11—H11	0.9300
O1—C1—N5	124.34 (18)	O13—C13—H131	109.7
O1—C1—N2	120.78 (18)	C12—C13—H131	109.7
N5—C1—N2	114.83 (17)	O13—C13—H132	109.7
C1—N2—O3	114.16 (16)	C12—C13—H132	109.7
C1—N2—C7	124.46 (16)	H131—C13—H132	108.2
O3—N2—C7	114.70 (15)	C14—O13—C13	113.70 (17)
N2—O3—C4	109.54 (17)	N15—C14—O13	122.9 (2)
O3—C4—H4B	109.5	N15—C14—C18	112.3 (2)
O3—C4—H4A	109.5	O13—C14—C18	124.9 (2)
H4B—C4—H4A	109.5	C14—N15—N16	104.28 (18)
O3—C4—H4C	109.5	C17—N16—N15	110.6 (2)
H4B—C4—H4C	109.5	C17—N16—C19	129.7 (2)
H4A—C4—H4C	109.5	N15—N16—C19	119.64 (17)
C1—N5—N6	121.57 (17)	C18—C17—N16	108.3 (2)
C1—N5—H51	121.9 (15)	C18—C17—H17	125.8
N6—N5—H51	115.1 (15)	N16—C17—H17	125.8
N5—N6—H61	107.8 (15)	C17—C18—C14	104.5 (2)
N5—N6—H62	108.1 (16)	C17—C18—H18	127.7
H61—N6—H62	104 (2)	C14—C18—H18	127.7
C8—C7—C12	120.9 (2)	C20—C19—C24	120.1 (2)
C8—C7—N2	120.0 (2)	C20—C19—N16	119.6 (2)
C12—C7—N2	119.00 (19)	C24—C19—N16	120.3 (2)
C9—C8—C7	120.1 (2)	C21—C20—C19	120.1 (2)
C9—C8—H8	120.0	C21—C20—H20	120.0
C7—C8—H8	120.0	C19—C20—H20	120.0
C10—C9—C8	119.8 (3)	C20—C21—C22	119.3 (2)
C10—C9—H9	120.1	C20—C21—H21	120.4
C8—C9—H9	120.1	C22—C21—H21	120.4
C9—C10—C11	120.4 (2)	C23—C22—C21	120.7 (2)
C9—C10—H10	119.8	C23—C22—Cl1	120.6 (2)
C11—C10—H10	119.8	C21—C22—Cl1	118.7 (2)
C10—C11—C12	121.2 (2)	C22—C23—C24	120.4 (2)
C10—C11—H11	119.4	C22—C23—H23	119.8
C12—C11—H11	119.4	C24—C23—H23	119.8
C11—C12—C7	117.6 (2)	C23—C24—C19	119.4 (2)
C11—C12—C13	121.8 (2)	C23—C24—H24	120.3
C7—C12—C13	120.64 (18)	C19—C24—H24	120.3
O13—C13—C12	109.90 (17)
O1—C1—N2—O3	158.54 (18)	C13—O13—C14—N15	21.2 (3)
N5—C1—N2—O3	−23.9 (3)	C13—O13—C14—C18	−159.2 (2)
O1—C1—N2—C7	8.8 (3)	O13—C14—N15—N16	179.8 (2)
N5—C1—N2—C7	−173.6 (2)	C18—C14—N15—N16	0.1 (3)
C1—N2—O3—C4	125.3 (2)	C14—N15—N16—C17	0.0 (2)
C7—N2—O3—C4	−81.9 (2)	C14—N15—N16—C19	177.28 (18)
O1—C1—N5—N6	7.2 (3)	N15—N16—C17—C18	−0.2 (3)
N2—C1—N5—N6	−170.22 (19)	C19—N16—C17—C18	−177.1 (2)
C1—N2—C7—C8	118.9 (2)	N16—C17—C18—C14	0.3 (3)
O3—N2—C7—C8	−30.7 (3)	N15—C14—C18—C17	−0.2 (3)
C1—N2—C7—C12	−65.6 (3)	O13—C14—C18—C17	−179.9 (2)
O3—N2—C7—C12	144.89 (18)	C17—N16—C19—C20	157.9 (2)
C12—C7—C8—C9	1.2 (4)	N15—N16—C19—C20	−18.7 (3)
N2—C7—C8—C9	176.6 (2)	C17—N16—C19—C24	−21.4 (3)
C7—C8—C9—C10	0.5 (4)	N15—N16—C19—C24	161.9 (2)
C8—C9—C10—C11	−1.5 (4)	C24—C19—C20—C21	−1.2 (3)
C9—C10—C11—C12	0.9 (4)	N16—C19—C20—C21	179.50 (19)
C10—C11—C12—C7	0.6 (3)	C19—C20—C21—C22	1.2 (3)
C10—C11—C12—C13	179.9 (2)	C20—C21—C22—C23	−0.4 (3)
C8—C7—C12—C11	−1.7 (3)	C20—C21—C22—Cl1	−178.87 (16)
N2—C7—C12—C11	−177.21 (19)	C21—C22—C23—C24	−0.3 (4)
C8—C7—C12—C13	179.1 (2)	Cl1—C22—C23—C24	178.14 (19)
N2—C7—C12—C13	3.6 (3)	C22—C23—C24—C19	0.2 (4)
C11—C12—C13—O13	27.3 (3)	C20—C19—C24—C23	0.5 (3)
C7—C12—C13—O13	−153.51 (19)	N16—C19—C24—C23	179.8 (2)
C12—C13—O13—C14	−178.05 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H51···N6i	0.88 (2)	2.28 (2)	3.080 (3)	153 (2)
N6—H61···O1ii	0.86 (2)	2.34 (2)	3.120 (3)	152 (2)
N6—H62···N15ii	0.87 (3)	2.56 (3)	3.408 (3)	164 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H51⋯N6i	0.88 (2)	2.28 (2)	3.080 (3)	153 (2)
N6—H61⋯O1ii	0.86 (2)	2.34 (2)	3.120 (3)	152 (2)
N6—H62⋯N15ii	0.87 (3)	2.56 (3)	3.408 (3)	164 (2)

Symmetry codes: (i) ; (ii) .