Diniconazole

Xiong, Z.-Q.; Chen, J.-Z.; Wen, S.-H.; Nie, X.-L.

doi:10.1107/S160053681004804X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3278

https://doi.org/10.1107/S160053681004804X

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Diniconazole

Zhi-Qiang Xiong,^a,^b Jin-Zhu Chen,^a Shi-He Wen ^a and Xu-Liang Nie ^a ^*

^aDepartment of Chemistry, Jiangxi Agricultural University, Nanchang 330045, People's Republic of China, and ^bInstrumental Analysis Center, Nanchang Hangkong University, Nanchang 330063, People's Republic of China
^*Correspondence e-mail: niexuliang1981@163.com

(Received 16 November 2010; accepted 18 November 2010; online 24 November 2010)

The asymmetric unit of the title compound [systematic name: (E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol], C₁₅H₁₇Cl₂N₃O, contains two molecules in which the dihedral angles between the triazole and benzene rings are 9.4 (2) and 35.0 (2)°. In the crystal, the molecules are linked by O—H⋯N hydrogen bonds, forming C(7) chains propagating in [010].

Related literature

For background to the use of diniconazole as a fungicide, see: Sumitomo Chemical (1984 ). For further synthetic details, see: Xia et al. (2001 ).

Experimental

Crystal data

C₁₅H₁₇Cl₂N₃O
M_r = 326.22
Monoclinic, P 2₁ /n
a = 7.2321 (15) Å
b = 20.248 (4) Å
c = 22.449 (5) Å
β = 96.072 (2)°
V = 3268.8 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 296 K
0.22 × 0.18 × 0.07 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.917, T_max = 0.973
24930 measured reflections
6074 independent reflections
4232 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.179
S = 1.02
6074 reflections
391 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.06 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N6ⁱ	0.82	2.04	2.844 (3)	165
O2—H2⋯N3ⁱⁱ	0.82	2.01	2.812 (4)	166
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x, y-1, z.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681004804X/hb5745sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004804X/hb5745Isup2.hkl

checkCIF report

Related literature top

For background to the use of diniconazole as a fungicide, see: Sumitomo Chemical (1984). For further synthetic details, see: Xia et al. (2001).

Experimental top

The synthesis process of diniconazole is carried out by the three steps of condensing, using a-triazolylpinacolone and 2,4-dichlorobenzaldehyde for material shifting and reduing, using a modified Xia reaction (Xia et al., 2001). Diniconazole was recrystallized from ethanol, and colourless blocks were obtained by slow concentration of a water/ethanol solution. m.p. 134–138 °C (m.p.134–156°C). Anal. Calcd. For C15H17Cl2N3O (%) (Mr = 326.22): C, 55.23; H, 5.25; N, 12.88. Found (%): C, 55.21; H, 5.36; N, 12.90.

Structure description top

For background to the use of diniconazole as a fungicide, see: Sumitomo Chemical (1984). For further synthetic details, see: Xia et al. (2001).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 40% probability level.
	Fig. 2. The crystal packing of (I), showing hydrogen-bonded chains; H-bonds are shown as dashed lines.

1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H- 1,2,4-triazol-1-yl)pent-1-en-3-ol top

Crystal data top

C₁₅H₁₇Cl₂N₃O	F(000) = 1360
M_r = 326.22	D_x = 1.326 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6731 reflections
a = 7.2321 (15) Å	θ = 2.9–23.7°
b = 20.248 (4) Å	µ = 0.40 mm⁻¹
c = 22.449 (5) Å	T = 296 K
β = 96.072 (2)°	Block, colourless
V = 3268.8 (12) Å³	0.22 × 0.18 × 0.07 mm
Z = 8

Data collection top

Bruker SMART APEX CCD diffractometer	6074 independent reflections
Radiation source: fine-focus sealed tube	4232 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
φ and ω scans	θ_max = 25.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −8→8
T_min = 0.917, T_max = 0.973	k = −24→24
24930 measured reflections	l = −27→27

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.179	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0857P)² + 2.8116P] where P = (F_o² + 2F_c²)/3
6074 reflections	(Δ/σ)_max < 0.001
391 parameters	Δρ_max = 1.06 e Å⁻³
1 restraint	Δρ_min = −0.53 e Å⁻³

Crystal data top

C₁₅H₁₇Cl₂N₃O	V = 3268.8 (12) Å³
M_r = 326.22	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.2321 (15) Å	µ = 0.40 mm⁻¹
b = 20.248 (4) Å	T = 296 K
c = 22.449 (5) Å	0.22 × 0.18 × 0.07 mm
β = 96.072 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	6074 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	4232 reflections with I > 2σ(I)
T_min = 0.917, T_max = 0.973	R_int = 0.028
24930 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	1 restraint
wR(F²) = 0.179	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 1.06 e Å⁻³
6074 reflections	Δρ_min = −0.53 e Å⁻³
391 parameters

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	U_iso*/U_eq
Cl2	0.65600 (18)	0.67176 (5)	0.77688 (5)	0.0814 (4)
Cl3	0.70579 (19)	0.44904 (6)	1.11219 (5)	0.0883 (4)
Cl1	0.5999 (2)	0.83181 (5)	0.96433 (4)	0.0888 (4)
Cl4	0.82764 (18)	0.21724 (9)	1.22070 (6)	0.1187 (6)
N4	0.8131 (4)	0.43310 (12)	0.90776 (11)	0.0446 (6)
C17	0.7857 (5)	0.37039 (19)	1.10971 (15)	0.0576 (9)
C22	0.8479 (5)	0.34644 (17)	1.05758 (14)	0.0492 (8)
C19	0.8393 (5)	0.2666 (2)	1.15758 (18)	0.0713 (12)
C21	0.9102 (5)	0.28044 (19)	1.05634 (16)	0.0603 (9)
C20	0.9004 (5)	0.2411 (2)	1.10768 (19)	0.0701 (11)
H20	0.9365	0.1970	1.1072	0.084*
C18	0.7834 (5)	0.3313 (2)	1.16074 (16)	0.0705 (11)
H18	0.7452	0.3484	1.1959	0.085*
O2	0.7417 (4)	0.29529 (11)	0.87882 (10)	0.0582 (6)
H2	0.7670	0.2567	0.8872	0.087*
C24	0.7835 (4)	0.38187 (14)	0.95063 (13)	0.0425 (7)
C25	0.6605 (5)	0.32546 (15)	0.92710 (13)	0.0459 (7)
H25	0.6629	0.2926	0.9592	0.055*
N6	0.8689 (4)	0.48664 (14)	0.82749 (12)	0.0600 (8)
N5	0.7781 (4)	0.49744 (13)	0.91967 (12)	0.0577 (8)
C30	0.8680 (5)	0.42838 (17)	0.85327 (14)	0.0536 (8)
H30	0.9012	0.3891	0.8357	0.064*
C26	0.4538 (5)	0.34365 (17)	0.90934 (15)	0.0539 (8)
C23	0.8597 (5)	0.39100 (16)	1.00591 (14)	0.0490 (8)
H23	0.9283	0.4296	1.0132	0.059*
C31	0.8128 (6)	0.52653 (17)	0.87023 (17)	0.0631 (10)
H31	0.7997	0.5719	0.8648	0.076*
C29	0.4280 (5)	0.38712 (18)	0.85297 (16)	0.0620 (9)
H29A	0.4925	0.3677	0.8221	0.093*
H29B	0.4774	0.4304	0.8623	0.093*
H29C	0.2980	0.3905	0.8393	0.093*
C28	0.3795 (6)	0.3783 (3)	0.96174 (19)	0.0833 (13)
H28A	0.2479	0.3849	0.9532	0.125*
H28B	0.4399	0.4203	0.9681	0.125*
H28C	0.4037	0.3517	0.9971	0.125*
C27	0.3483 (6)	0.2788 (2)	0.8956 (2)	0.0816 (13)
H27A	0.2184	0.2880	0.8858	0.122*
H27B	0.3644	0.2505	0.9300	0.122*
H27C	0.3959	0.2573	0.8623	0.122*
O1	0.4857 (4)	1.04993 (11)	0.77059 (10)	0.0589 (6)
H1	0.5461	1.0329	0.7457	0.088*
C10	0.4536 (5)	1.00280 (15)	0.81480 (14)	0.0478 (8)
H10	0.4444	0.9597	0.7948	0.057*
C9	0.6143 (4)	0.99840 (14)	0.86293 (14)	0.0440 (7)
C7	0.6734 (4)	0.87704 (15)	0.85638 (14)	0.0466 (7)
C2	0.6358 (5)	0.82160 (16)	0.88971 (14)	0.0500 (8)
C8	0.6993 (5)	0.94335 (15)	0.88313 (15)	0.0484 (8)
H8	0.7829	0.9470	0.9174	0.058*
C5	0.6972 (5)	0.80365 (17)	0.77202 (16)	0.0564 (9)
H5	0.7174	0.7976	0.7322	0.068*
C4	0.6598 (5)	0.75077 (15)	0.80720 (16)	0.0533 (8)
C3	0.6285 (5)	0.75888 (16)	0.86631 (16)	0.0549 (8)
H3	0.6031	0.7228	0.8897	0.066*
C6	0.7044 (5)	0.86592 (16)	0.79699 (15)	0.0532 (8)
H6	0.7307	0.9017	0.7734	0.064*
C11	0.2617 (5)	1.01600 (18)	0.83808 (16)	0.0569 (9)
C14	0.1120 (6)	1.0049 (2)	0.7858 (2)	0.0780 (12)
H14A	0.1323	1.0345	0.7537	0.117*
H14B	−0.0082	1.0132	0.7987	0.117*
H14C	0.1178	0.9601	0.7721	0.117*
C12	0.2327 (6)	0.9669 (3)	0.8877 (2)	0.1003 (17)
H12A	0.2481	0.9228	0.8735	0.150*
H12B	0.1095	0.9720	0.8994	0.150*
H12C	0.3222	0.9752	0.9216	0.150*
C13	0.2417 (6)	1.0870 (2)	0.8601 (2)	0.0906 (15)
H13A	0.1164	1.0941	0.8691	0.136*
H13B	0.2702	1.1173	0.8295	0.136*
H13C	0.3259	1.0940	0.8956	0.136*
N1	0.6761 (4)	1.05896 (12)	0.89188 (12)	0.0494 (7)
N3	0.7609 (5)	1.16084 (14)	0.91014 (16)	0.0682 (9)
N2	0.7569 (6)	1.05941 (16)	0.94929 (15)	0.0791 (10)
C15	0.6829 (5)	1.12015 (16)	0.86994 (17)	0.0593 (9)
H15	0.6380	1.1322	0.8311	0.071*
C16	0.8031 (7)	1.1211 (2)	0.9574 (2)	0.0840 (13)
H16	0.8614	1.1367	0.9936	0.101*
H21	1.0000 (13)	0.2641 (5)	1.0193 (4)	−0.050 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl2	0.1121 (9)	0.0410 (5)	0.0934 (8)	0.0038 (5)	0.0210 (6)	−0.0089 (5)
Cl3	0.1113 (9)	0.0765 (7)	0.0782 (7)	0.0223 (6)	0.0151 (6)	−0.0110 (5)
Cl1	0.1515 (12)	0.0683 (6)	0.0495 (5)	−0.0040 (7)	0.0248 (6)	0.0095 (5)
Cl4	0.0886 (9)	0.1778 (15)	0.0906 (9)	0.0219 (9)	0.0131 (7)	0.0851 (10)
N4	0.0555 (16)	0.0405 (14)	0.0382 (13)	−0.0042 (12)	0.0067 (12)	0.0008 (11)
C17	0.056 (2)	0.069 (2)	0.0459 (18)	−0.0022 (17)	0.0006 (16)	−0.0012 (16)
C22	0.0500 (18)	0.059 (2)	0.0368 (16)	−0.0066 (15)	−0.0038 (14)	0.0024 (14)
C19	0.053 (2)	0.101 (3)	0.058 (2)	0.005 (2)	−0.0044 (18)	0.033 (2)
C21	0.057 (2)	0.062 (2)	0.059 (2)	0.0051 (17)	−0.0058 (17)	0.0132 (17)
C20	0.063 (2)	0.072 (3)	0.073 (3)	0.012 (2)	−0.002 (2)	0.026 (2)
C18	0.060 (2)	0.110 (4)	0.0413 (19)	−0.001 (2)	0.0067 (17)	0.006 (2)
O2	0.0883 (18)	0.0394 (12)	0.0486 (13)	0.0003 (12)	0.0155 (12)	−0.0052 (10)
C24	0.0518 (18)	0.0394 (16)	0.0367 (15)	0.0001 (13)	0.0060 (13)	0.0019 (12)
C25	0.064 (2)	0.0397 (16)	0.0340 (15)	−0.0045 (14)	0.0038 (14)	0.0038 (12)
N6	0.080 (2)	0.0554 (17)	0.0465 (16)	−0.0132 (15)	0.0149 (15)	0.0077 (13)
N5	0.084 (2)	0.0400 (15)	0.0513 (16)	−0.0028 (14)	0.0159 (15)	0.0001 (12)
C30	0.069 (2)	0.0512 (19)	0.0422 (17)	−0.0085 (16)	0.0126 (16)	−0.0022 (14)
C26	0.058 (2)	0.057 (2)	0.0450 (18)	−0.0062 (16)	−0.0011 (16)	0.0065 (15)
C23	0.058 (2)	0.0473 (18)	0.0416 (17)	−0.0051 (15)	0.0029 (15)	−0.0006 (14)
C31	0.088 (3)	0.0420 (18)	0.060 (2)	−0.0079 (18)	0.014 (2)	0.0083 (16)
C29	0.066 (2)	0.059 (2)	0.059 (2)	0.0001 (18)	−0.0065 (18)	0.0087 (17)
C28	0.062 (2)	0.124 (4)	0.066 (3)	0.011 (2)	0.014 (2)	−0.001 (3)
C27	0.081 (3)	0.083 (3)	0.075 (3)	−0.035 (2)	−0.015 (2)	0.022 (2)
O1	0.0888 (18)	0.0460 (13)	0.0459 (13)	0.0125 (12)	0.0254 (12)	0.0075 (10)
C10	0.065 (2)	0.0362 (16)	0.0441 (17)	0.0056 (14)	0.0131 (16)	0.0008 (13)
C9	0.0526 (18)	0.0358 (15)	0.0464 (17)	0.0004 (13)	0.0187 (15)	0.0000 (13)
C7	0.0503 (18)	0.0379 (16)	0.0523 (18)	0.0058 (14)	0.0088 (15)	0.0058 (13)
C2	0.057 (2)	0.0462 (18)	0.0470 (18)	0.0035 (15)	0.0052 (15)	0.0076 (14)
C8	0.0511 (19)	0.0426 (17)	0.0522 (18)	−0.0008 (14)	0.0092 (15)	0.0019 (14)
C5	0.070 (2)	0.0478 (18)	0.0539 (19)	0.0079 (16)	0.0181 (17)	0.0012 (15)
C4	0.058 (2)	0.0369 (17)	0.065 (2)	0.0070 (15)	0.0086 (17)	0.0001 (15)
C3	0.064 (2)	0.0380 (17)	0.063 (2)	0.0019 (15)	0.0069 (17)	0.0126 (15)
C6	0.066 (2)	0.0404 (17)	0.0561 (19)	0.0059 (15)	0.0193 (17)	0.0100 (15)
C11	0.056 (2)	0.064 (2)	0.0516 (19)	0.0035 (17)	0.0090 (16)	0.0021 (16)
C14	0.067 (3)	0.085 (3)	0.080 (3)	0.005 (2)	−0.003 (2)	0.001 (2)
C12	0.066 (3)	0.148 (5)	0.090 (3)	−0.004 (3)	0.025 (2)	0.046 (3)
C13	0.074 (3)	0.099 (3)	0.102 (3)	0.019 (3)	0.023 (3)	−0.038 (3)
N1	0.0616 (17)	0.0397 (14)	0.0490 (15)	−0.0004 (12)	0.0154 (13)	−0.0025 (11)
N3	0.089 (2)	0.0410 (16)	0.076 (2)	−0.0033 (15)	0.0162 (18)	−0.0121 (16)
N2	0.124 (3)	0.0556 (19)	0.0550 (19)	−0.0067 (19)	−0.0017 (19)	−0.0046 (15)
C15	0.076 (2)	0.0361 (17)	0.068 (2)	0.0006 (16)	0.0168 (19)	0.0019 (16)
C16	0.125 (4)	0.055 (2)	0.070 (3)	−0.005 (2)	−0.002 (3)	−0.017 (2)

Geometric parameters (Å, º) top

Cl2—C4	1.738 (3)	C27—H27B	0.9600
Cl3—C17	1.697 (4)	C27—H27C	0.9600
Cl1—C2	1.734 (3)	O1—C10	1.413 (4)
Cl4—C19	1.743 (4)	O1—H1	0.8200
N4—C30	1.329 (4)	C10—C9	1.504 (5)
N4—N5	1.359 (4)	C10—C11	1.557 (5)
N4—C24	1.446 (4)	C10—H10	0.9800
C17—C22	1.385 (5)	C9—C8	1.329 (4)
C17—C18	1.394 (5)	C9—N1	1.437 (4)
C22—C21	1.411 (5)	C7—C2	1.392 (4)
C22—C23	1.479 (4)	C7—C6	1.393 (5)
C19—C20	1.349 (6)	C7—C8	1.475 (4)
C19—C18	1.375 (6)	C2—C3	1.373 (5)
C21—C20	1.409 (5)	C8—H8	0.9300
C21—H21	1.157 (7)	C5—C4	1.374 (5)
C20—H20	0.9300	C5—C6	1.379 (5)
C18—H18	0.9300	C5—H5	0.9300
O2—C25	1.424 (4)	C4—C3	1.379 (5)
O2—H2	0.8200	C3—H3	0.9300
C24—C23	1.317 (4)	C6—H6	0.9300
C24—C25	1.508 (4)	C11—C12	1.524 (5)
C25—C26	1.550 (5)	C11—C14	1.527 (6)
C25—H25	0.9800	C11—C13	1.532 (6)
N6—C30	1.314 (4)	C14—H14A	0.9600
N6—C31	1.349 (5)	C14—H14B	0.9600
N5—C31	1.304 (4)	C14—H14C	0.9600
C30—H30	0.9300	C12—H12A	0.9600
C26—C28	1.516 (5)	C12—H12B	0.9600
C26—C27	1.534 (5)	C12—H12C	0.9600
C26—C29	1.536 (5)	C13—H13A	0.9600
C23—H23	0.9300	C13—H13B	0.9600
C31—H31	0.9300	C13—H13C	0.9600
C29—H29A	0.9600	N1—C15	1.336 (4)
C29—H29B	0.9600	N1—N2	1.358 (4)
C29—H29C	0.9600	N3—C15	1.305 (5)
C28—H28A	0.9600	N3—C16	1.341 (5)
C28—H28B	0.9600	N2—C16	1.302 (5)
C28—H28C	0.9600	C15—H15	0.9300
C27—H27A	0.9600	C16—H16	0.9300

C30—N4—N5	109.3 (3)	C10—O1—H1	109.5
C30—N4—C24	129.9 (3)	O1—C10—C9	111.9 (3)
N5—N4—C24	120.8 (2)	O1—C10—C11	109.8 (3)
C22—C17—C18	121.9 (4)	C9—C10—C11	114.7 (3)
C22—C17—Cl3	119.9 (3)	O1—C10—H10	106.7
C18—C17—Cl3	118.2 (3)	C9—C10—H10	106.7
C17—C22—C21	118.8 (3)	C11—C10—H10	106.7
C17—C22—C23	120.0 (3)	C8—C9—N1	116.8 (3)
C21—C22—C23	121.1 (3)	C8—C9—C10	126.1 (3)
C20—C19—C18	122.1 (4)	N1—C9—C10	117.0 (3)
C20—C19—Cl4	120.2 (4)	C2—C7—C6	116.4 (3)
C18—C19—Cl4	117.7 (3)	C2—C7—C8	122.6 (3)
C20—C21—C22	118.4 (4)	C6—C7—C8	120.7 (3)
C20—C21—H21	120.4 (6)	C3—C2—C7	122.8 (3)
C22—C21—H21	119.3 (6)	C3—C2—Cl1	118.4 (2)
C19—C20—C21	120.8 (4)	C7—C2—Cl1	118.7 (3)
C19—C20—H20	119.6	C9—C8—C7	126.2 (3)
C21—C20—H20	119.6	C9—C8—H8	116.9
C19—C18—C17	118.0 (4)	C7—C8—H8	116.9
C19—C18—H18	121.0	C4—C5—C6	118.7 (3)
C17—C18—H18	121.0	C4—C5—H5	120.7
C25—O2—H2	109.5	C6—C5—H5	120.7
C23—C24—N4	116.7 (3)	C5—C4—C3	121.5 (3)
C23—C24—C25	127.5 (3)	C5—C4—Cl2	119.2 (3)
N4—C24—C25	115.7 (2)	C3—C4—Cl2	119.3 (3)
O2—C25—C24	108.4 (3)	C2—C3—C4	118.3 (3)
O2—C25—C26	111.7 (3)	C2—C3—H3	120.8
C24—C25—C26	115.3 (3)	C4—C3—H3	120.8
O2—C25—H25	107.0	C5—C6—C7	122.3 (3)
C24—C25—H25	107.0	C5—C6—H6	118.9
C26—C25—H25	107.0	C7—C6—H6	118.9
C30—N6—C31	102.0 (3)	C12—C11—C14	109.0 (4)
C31—N5—N4	102.1 (3)	C12—C11—C13	110.5 (4)
N6—C30—N4	110.9 (3)	C14—C11—C13	107.6 (3)
N6—C30—H30	124.5	C12—C11—C10	109.3 (3)
N4—C30—H30	124.5	C14—C11—C10	107.5 (3)
C28—C26—C27	110.1 (3)	C13—C11—C10	112.8 (3)
C28—C26—C29	110.6 (3)	C11—C14—H14A	109.5
C27—C26—C29	108.1 (3)	C11—C14—H14B	109.5
C28—C26—C25	108.7 (3)	H14A—C14—H14B	109.5
C27—C26—C25	107.1 (3)	C11—C14—H14C	109.5
C29—C26—C25	112.2 (3)	H14A—C14—H14C	109.5
C24—C23—C22	126.9 (3)	H14B—C14—H14C	109.5
C24—C23—H23	116.6	C11—C12—H12A	109.5
C22—C23—H23	116.6	C11—C12—H12B	109.5
N5—C31—N6	115.7 (3)	H12A—C12—H12B	109.5
N5—C31—H31	122.1	C11—C12—H12C	109.5
N6—C31—H31	122.1	H12A—C12—H12C	109.5
C26—C29—H29A	109.5	H12B—C12—H12C	109.5
C26—C29—H29B	109.5	C11—C13—H13A	109.5
H29A—C29—H29B	109.5	C11—C13—H13B	109.5
C26—C29—H29C	109.5	H13A—C13—H13B	109.5
H29A—C29—H29C	109.5	C11—C13—H13C	109.5
H29B—C29—H29C	109.5	H13A—C13—H13C	109.5
C26—C28—H28A	109.5	H13B—C13—H13C	109.5
C26—C28—H28B	109.5	C15—N1—N2	108.3 (3)
H28A—C28—H28B	109.5	C15—N1—C9	130.3 (3)
C26—C28—H28C	109.5	N2—N1—C9	121.1 (3)
H28A—C28—H28C	109.5	C15—N3—C16	102.4 (3)
H28B—C28—H28C	109.5	C16—N2—N1	102.6 (3)
C26—C27—H27A	109.5	N3—C15—N1	111.1 (3)
C26—C27—H27B	109.5	N3—C15—H15	124.4
H27A—C27—H27B	109.5	N1—C15—H15	124.4
C26—C27—H27C	109.5	N2—C16—N3	115.5 (4)
H27A—C27—H27C	109.5	N2—C16—H16	122.2
H27B—C27—H27C	109.5	N3—C16—H16	122.2

C18—C17—C22—C21	0.2 (5)	O1—C10—C9—C8	−130.0 (3)
Cl3—C17—C22—C21	−178.8 (3)	C11—C10—C9—C8	104.2 (4)
C18—C17—C22—C23	−175.9 (3)	O1—C10—C9—N1	53.3 (3)
Cl3—C17—C22—C23	5.2 (5)	C11—C10—C9—N1	−72.6 (3)
C17—C22—C21—C20	2.1 (5)	C6—C7—C2—C3	−0.1 (5)
C23—C22—C21—C20	178.1 (3)	C8—C7—C2—C3	−173.9 (3)
C18—C19—C20—C21	0.3 (6)	C6—C7—C2—Cl1	178.9 (3)
Cl4—C19—C20—C21	179.9 (3)	C8—C7—C2—Cl1	5.2 (5)
C22—C21—C20—C19	−2.4 (6)	N1—C9—C8—C7	−173.0 (3)
C20—C19—C18—C17	2.0 (6)	C10—C9—C8—C7	10.3 (5)
Cl4—C19—C18—C17	−177.6 (3)	C2—C7—C8—C9	−129.4 (4)
C22—C17—C18—C19	−2.2 (6)	C6—C7—C8—C9	57.1 (5)
Cl3—C17—C18—C19	176.7 (3)	C6—C5—C4—C3	0.4 (5)
C30—N4—C24—C23	131.4 (4)	C6—C5—C4—Cl2	−178.4 (3)
N5—N4—C24—C23	−51.0 (4)	C7—C2—C3—C4	−0.1 (5)
C30—N4—C24—C25	−51.3 (5)	Cl1—C2—C3—C4	−179.1 (3)
N5—N4—C24—C25	126.2 (3)	C5—C4—C3—C2	−0.1 (5)
C23—C24—C25—O2	−123.9 (3)	Cl2—C4—C3—C2	178.7 (3)
N4—C24—C25—O2	59.2 (3)	C4—C5—C6—C7	−0.5 (5)
C23—C24—C25—C26	110.0 (4)	C2—C7—C6—C5	0.4 (5)
N4—C24—C25—C26	−66.9 (3)	C8—C7—C6—C5	174.3 (3)
C30—N4—N5—C31	0.8 (4)	O1—C10—C11—C12	−177.4 (3)
C24—N4—N5—C31	−177.1 (3)	C9—C10—C11—C12	−50.4 (4)
C31—N6—C30—N4	0.5 (4)	O1—C10—C11—C14	64.5 (4)
N5—N4—C30—N6	−0.9 (4)	C9—C10—C11—C14	−168.6 (3)
C24—N4—C30—N6	176.8 (3)	O1—C10—C11—C13	−54.0 (4)
O2—C25—C26—C28	−177.3 (3)	C9—C10—C11—C13	72.9 (4)
C24—C25—C26—C28	−53.0 (4)	C8—C9—N1—C15	148.1 (4)
O2—C25—C26—C27	63.7 (3)	C10—C9—N1—C15	−34.9 (5)
C24—C25—C26—C27	−171.9 (3)	C8—C9—N1—N2	−25.6 (4)
O2—C25—C26—C29	−54.7 (4)	C10—C9—N1—N2	151.4 (3)
C24—C25—C26—C29	69.7 (4)	C15—N1—N2—C16	1.0 (5)
N4—C24—C23—C22	179.3 (3)	C9—N1—N2—C16	176.0 (3)
C25—C24—C23—C22	2.5 (6)	C16—N3—C15—N1	0.7 (4)
C17—C22—C23—C24	−125.7 (4)	N2—N1—C15—N3	−1.1 (4)
C21—C22—C23—C24	58.3 (5)	C9—N1—C15—N3	−175.5 (3)
N4—N5—C31—N6	−0.5 (5)	N1—N2—C16—N3	−0.6 (6)
C30—N6—C31—N5	0.0 (5)	C15—N3—C16—N2	0.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N6ⁱ	0.82	2.04	2.844 (3)	165
O2—H2···N3ⁱⁱ	0.82	2.01	2.812 (4)	166

Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₇Cl₂N₃O
M_r	326.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	7.2321 (15), 20.248 (4), 22.449 (5)
β (°)	96.072 (2)
V (Å³)	3268.8 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.22 × 0.18 × 0.07

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.917, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	24930, 6074, 4232
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.179, 1.02
No. of reflections	6074
No. of parameters	391
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.06, −0.53

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N6ⁱ	0.82	2.04	2.844 (3)	165
O2—H2···N3ⁱⁱ	0.82	2.01	2.812 (4)	166

Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) x, y−1, z.

Acknowledgements

This work was supported by the Natural Science Foundation of Jiangxi Agricultural University, China (2964).

References

Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisoconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sumitomo Chemical (1984). Jpn Pestic. Soc. 6, 229–236. Google Scholar
Xia, H. Y., Duan, Z. X., Tu, Y. M. & Liu, J. H. (2001). Chin. J. Pestic. 40, 12–14. CAS Google Scholar