Literature DB >> 21577964

1-[(6-Chloro-3-pyrid-yl)meth-yl]-5-eth-oxy-8-nitro-1,2,3,5,6,7-hexa-hydro-imidazo[1,2-a]pyridine.

Abstract

In the title compound, C(15)H(19)ClN(4)O(3), an active agrochemical possessing insecticidal activity, the dihedral angle between the mean planes passing through the pyridine ring and the five-membered ring is 87.3 (2)°. The fused pyridine ring adopts a twisted sofa conformation. The mol-ecular structure features close intra-molecular C-H⋯N and C-H⋯O hydrogen bonding.

Entities: Chemical Disease Gene Species

Year: 2009 PMID： 21577964 PMCID： PMC2970492 DOI： 10.1107/S1600536809037660

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For related literature, see: Kagabu et al. (2002 ▶); Moriya et al. (1992 ▶); Tian et al. (2007 ▶); Tokumitsu (1990 ▶).

Experimental

Crystal data

C15H19ClN4O3 M = 338.79 Monoclinic, a = 17.021 (3) Å b = 5.5737 (8) Å c = 18.334 (3) Å β = 112.097 (3)° V = 1611.6 (4) Å3 Z = 4 Mo Kα radiation μ = 0.26 mm−1 T = 290 K 0.50 × 0.24 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.922, T max = 0.969 8970 measured reflections 3486 independent reflections 1870 reflections with I > 2σ(I) R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.049 wR(F 2) = 0.135 S = 0.82 3486 reflections 210 parameters H-atom parameters constrained Δρmax = 0.32 e Å−3 Δρmin = −0.24 e Å−3 Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037660/bx2230sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037660/bx2230Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₅H₁₉ClN₄O₃	F(000) = 712
M_r = 338.79	D_x = 1.396 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1727 reflections
a = 17.021 (3) Å	θ = 4.8–47.4°
b = 5.5737 (8) Å	µ = 0.26 mm⁻¹
c = 18.334 (3) Å	T = 290 K
β = 112.097 (3)°	Prismatic, colourless
V = 1611.6 (4) Å³	0.50 × 0.24 × 0.12 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3486 independent reflections
Radiation source: fine-focus sealed tube	1870 reflections with I > 2σ(I)
graphite	R_int = 0.082
φ and ω scans	θ_max = 27.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −21→21
T_min = 0.922, T_max = 0.969	k = −7→7
8970 measured reflections	l = −23→13

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.135	w = 1/[σ²(F_o²) + (0.069P)²] where P = (F_o² + 2F_c²)/3
S = 0.82	(Δ/σ)_max = 0.044
3486 reflections	Δρ_max = 0.32 e Å⁻³
210 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (2)

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	U_iso*/U_eq
Cl	1.20916 (4)	0.34129 (13)	0.43476 (5)	0.0742 (3)
O1	0.58663 (11)	0.9036 (4)	0.35790 (10)	0.0669 (5)
O2	0.69588 (12)	0.4707 (4)	0.16844 (11)	0.0739 (6)
O3	0.81680 (12)	0.5033 (3)	0.26680 (11)	0.0653 (5)
N1	0.84352 (11)	0.9213 (3)	0.35853 (10)	0.0428 (5)
N2	0.71934 (11)	1.0384 (4)	0.35902 (11)	0.0484 (5)
N3	0.74299 (13)	0.5777 (4)	0.22900 (12)	0.0517 (5)
N4	1.05820 (12)	0.4680 (4)	0.42526 (12)	0.0542 (5)
C1	0.86309 (14)	1.0659 (5)	0.43064 (14)	0.0528 (6)
H1A	0.9076	1.1814	0.4361	0.063*
H1B	0.8806	0.9645	0.4770	0.063*
C2	0.77991 (15)	1.1909 (5)	0.41832 (15)	0.0594 (7)
H2A	0.7687	1.1946	0.4664	0.071*
H2B	0.7793	1.3533	0.3991	0.071*
C3	0.75815 (13)	0.9028 (4)	0.32102 (13)	0.0406 (5)
C4	0.71043 (14)	0.7723 (4)	0.25471 (13)	0.0451 (6)
C5	0.61813 (14)	0.8220 (5)	0.21354 (14)	0.0582 (7)
H5A	0.5857	0.6921	0.2236	0.070*
H5B	0.6045	0.8293	0.1572	0.070*
C6	0.59349 (15)	1.0563 (5)	0.24097 (15)	0.0602 (7)
H6A	0.5322	1.0689	0.2210	0.072*
H6B	0.6150	1.1890	0.2197	0.072*
C7	0.62807 (15)	1.0737 (5)	0.32935 (15)	0.0552 (7)
H7	0.6161	1.2340	0.3445	0.066*
C8	0.59553 (18)	0.9382 (6)	0.43754 (16)	0.0753 (9)
H8A	0.5732	1.0941	0.4433	0.090*
H8B	0.6551	0.9334	0.4715	0.090*
C9	0.5492 (2)	0.7483 (7)	0.46073 (19)	0.1023 (12)
H9A	0.4896	0.7620	0.4299	0.123*
H9B	0.5587	0.7652	0.5155	0.123*
H9C	0.5691	0.5940	0.4519	0.123*
C11	0.89956 (13)	0.9436 (4)	0.31525 (13)	0.0455 (6)
H11A	0.9131	1.1118	0.3130	0.055*
H11B	0.8695	0.8891	0.2617	0.055*
C12	0.98050 (13)	0.8050 (4)	0.35017 (12)	0.0393 (5)
C13	0.98935 (14)	0.6091 (4)	0.39838 (13)	0.0490 (6)
H13	0.9443	0.5719	0.4134	0.059*
C14	1.12093 (14)	0.5302 (4)	0.40378 (13)	0.0454 (6)
C15	1.12235 (14)	0.7269 (4)	0.35956 (13)	0.0465 (6)
H15	1.1699	0.7651	0.3486	0.056*
C16	1.05008 (14)	0.8655 (4)	0.33212 (13)	0.0462 (6)
H16	1.0480	1.0000	0.3014	0.055*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0596 (4)	0.0681 (5)	0.0967 (6)	0.0181 (3)	0.0313 (4)	0.0041 (4)
O1	0.0668 (11)	0.0879 (15)	0.0610 (12)	−0.0114 (10)	0.0413 (10)	−0.0097 (10)
O2	0.0778 (12)	0.0823 (14)	0.0702 (13)	−0.0259 (11)	0.0374 (11)	−0.0376 (11)
O3	0.0691 (12)	0.0575 (12)	0.0737 (13)	0.0125 (9)	0.0320 (10)	−0.0075 (9)
N1	0.0411 (11)	0.0494 (12)	0.0425 (11)	−0.0023 (8)	0.0210 (9)	−0.0026 (9)
N2	0.0439 (11)	0.0575 (13)	0.0477 (12)	0.0013 (9)	0.0216 (9)	−0.0130 (10)
N3	0.0583 (13)	0.0558 (13)	0.0503 (13)	−0.0090 (11)	0.0311 (11)	−0.0095 (11)
N4	0.0553 (12)	0.0513 (13)	0.0624 (14)	0.0059 (10)	0.0293 (11)	0.0106 (10)
C1	0.0529 (14)	0.0594 (16)	0.0473 (14)	−0.0102 (12)	0.0201 (12)	−0.0093 (12)
C2	0.0641 (16)	0.0623 (18)	0.0556 (16)	−0.0076 (13)	0.0269 (13)	−0.0186 (13)
C3	0.0447 (13)	0.0413 (13)	0.0407 (13)	0.0016 (10)	0.0216 (11)	0.0027 (10)
C4	0.0475 (13)	0.0493 (15)	0.0436 (14)	−0.0033 (11)	0.0231 (11)	−0.0055 (11)
C5	0.0476 (14)	0.081 (2)	0.0484 (15)	−0.0038 (13)	0.0204 (12)	−0.0060 (13)
C6	0.0466 (14)	0.082 (2)	0.0545 (16)	0.0109 (13)	0.0218 (12)	0.0084 (14)
C7	0.0500 (14)	0.0604 (17)	0.0626 (17)	0.0079 (12)	0.0297 (13)	−0.0033 (13)
C8	0.0739 (19)	0.104 (3)	0.0543 (18)	0.0098 (17)	0.0314 (15)	0.0030 (17)
C9	0.111 (3)	0.143 (3)	0.071 (2)	−0.020 (2)	0.055 (2)	0.006 (2)
C11	0.0480 (13)	0.0474 (14)	0.0479 (14)	−0.0009 (11)	0.0257 (11)	0.0059 (11)
C12	0.0426 (12)	0.0410 (13)	0.0379 (12)	−0.0033 (10)	0.0193 (10)	−0.0017 (10)
C13	0.0483 (14)	0.0533 (16)	0.0545 (15)	−0.0001 (11)	0.0299 (12)	0.0080 (12)
C14	0.0433 (13)	0.0477 (15)	0.0453 (14)	0.0016 (11)	0.0167 (11)	−0.0066 (11)
C15	0.0435 (13)	0.0538 (15)	0.0494 (14)	−0.0068 (11)	0.0257 (11)	−0.0048 (12)
C16	0.0488 (14)	0.0493 (14)	0.0451 (14)	−0.0073 (11)	0.0230 (11)	0.0045 (11)

Cl—C14	1.745 (2)	C5—H5A	0.9700
O1—C7	1.396 (3)	C5—H5B	0.9700
O1—C8	1.423 (3)	C6—C7	1.505 (4)
O2—N3	1.250 (2)	C6—H6A	0.9700
O3—N3	1.255 (2)	C6—H6B	0.9700
N1—C3	1.358 (3)	C7—H7	0.9800
N1—C11	1.458 (3)	C8—C9	1.475 (4)
N1—C1	1.475 (3)	C8—H8A	0.9700
N2—C3	1.356 (3)	C8—H8B	0.9700
N2—C7	1.453 (3)	C9—H9A	0.9600
N2—C2	1.457 (3)	C9—H9B	0.9600
N3—C4	1.379 (3)	C9—H9C	0.9600
N4—C14	1.316 (3)	C11—C12	1.497 (3)
N4—C13	1.342 (3)	C11—H11A	0.9700
C1—C2	1.517 (3)	C11—H11B	0.9700
C1—H1A	0.9700	C12—C13	1.377 (3)
C1—H1B	0.9700	C12—C16	1.386 (3)
C2—H2A	0.9700	C13—H13	0.9300
C2—H2B	0.9700	C14—C15	1.369 (3)
C3—C4	1.387 (3)	C15—C16	1.378 (3)
C4—C5	1.491 (3)	C15—H15	0.9300
C5—C6	1.514 (4)	C16—H16	0.9300

C7—O1—C8	114.8 (2)	H6A—C6—H6B	108.0
C3—N1—C11	121.70 (18)	O1—C7—N2	112.8 (2)
C3—N1—C1	109.47 (18)	O1—C7—C6	108.2 (2)
C11—N1—C1	117.89 (18)	N2—C7—C6	108.9 (2)
C3—N2—C7	122.79 (19)	O1—C7—H7	108.9
C3—N2—C2	111.33 (18)	N2—C7—H7	108.9
C7—N2—C2	123.86 (19)	C6—C7—H7	108.9
O2—N3—O3	120.5 (2)	O1—C8—C9	109.7 (3)
O2—N3—C4	118.2 (2)	O1—C8—H8A	109.7
O3—N3—C4	121.2 (2)	C9—C8—H8A	109.7
C14—N4—C13	115.5 (2)	O1—C8—H8B	109.7
N1—C1—C2	103.53 (17)	C9—C8—H8B	109.7
N1—C1—H1A	111.1	H8A—C8—H8B	108.2
C2—C1—H1A	111.1	C8—C9—H9A	109.5
N1—C1—H1B	111.1	C8—C9—H9B	109.5
C2—C1—H1B	111.1	H9A—C9—H9B	109.5
H1A—C1—H1B	109.0	C8—C9—H9C	109.5
N2—C2—C1	101.66 (19)	H9A—C9—H9C	109.5
N2—C2—H2A	111.4	H9B—C9—H9C	109.5
C1—C2—H2A	111.4	N1—C11—C12	114.11 (18)
N2—C2—H2B	111.4	N1—C11—H11A	108.7
C1—C2—H2B	111.4	C12—C11—H11A	108.7
H2A—C2—H2B	109.3	N1—C11—H11B	108.7
N2—C3—N1	109.43 (19)	C12—C11—H11B	108.7
N2—C3—C4	120.32 (19)	H11A—C11—H11B	107.6
N1—C3—C4	130.3 (2)	C13—C12—C16	116.7 (2)
N3—C4—C3	122.3 (2)	C13—C12—C11	123.00 (19)
N3—C4—C5	117.1 (2)	C16—C12—C11	120.3 (2)
C3—C4—C5	120.3 (2)	N4—C13—C12	124.8 (2)
C4—C5—C6	111.3 (2)	N4—C13—H13	117.6
C4—C5—H5A	109.4	C12—C13—H13	117.6
C6—C5—H5A	109.4	N4—C14—C15	125.8 (2)
C4—C5—H5B	109.4	N4—C14—Cl	116.08 (18)
C6—C5—H5B	109.4	C15—C14—Cl	118.11 (18)
H5A—C5—H5B	108.0	C14—C15—C16	117.0 (2)
C5—C6—C7	111.6 (2)	C14—C15—H15	121.5
C5—C6—H6A	109.3	C16—C15—H15	121.5
C7—C6—H6A	109.3	C15—C16—C12	120.1 (2)
C5—C6—H6B	109.3	C15—C16—H16	119.9
C7—C6—H6B	109.3	C12—C16—H16	119.9

C3—N1—C1—C2	−16.3 (3)	C8—O1—C7—N2	75.1 (3)
C11—N1—C1—C2	128.5 (2)	C8—O1—C7—C6	−164.3 (2)
C3—N2—C2—C1	−19.3 (3)	C3—N2—C7—O1	91.2 (3)
C7—N2—C2—C1	176.5 (2)	C2—N2—C7—O1	−106.4 (3)
N1—C1—C2—N2	20.5 (2)	C3—N2—C7—C6	−28.9 (3)
C7—N2—C3—N1	174.3 (2)	C2—N2—C7—C6	133.5 (2)
C2—N2—C3—N1	9.9 (3)	C5—C6—C7—O1	−67.8 (3)
C7—N2—C3—C4	−6.0 (3)	C5—C6—C7—N2	55.2 (3)
C2—N2—C3—C4	−170.4 (2)	C7—O1—C8—C9	180.0 (2)
C11—N1—C3—N2	−138.6 (2)	C3—N1—C11—C12	−140.6 (2)
C1—N1—C3—N2	4.7 (3)	C1—N1—C11—C12	79.0 (2)
C11—N1—C3—C4	41.7 (4)	N1—C11—C12—C13	23.2 (3)
C1—N1—C3—C4	−175.0 (2)	N1—C11—C12—C16	−159.4 (2)
O2—N3—C4—C3	−179.6 (2)	C14—N4—C13—C12	1.3 (3)
O3—N3—C4—C3	3.1 (3)	C16—C12—C13—N4	−3.6 (3)
O2—N3—C4—C5	7.1 (3)	C11—C12—C13—N4	173.9 (2)
O3—N3—C4—C5	−170.2 (2)	C13—N4—C14—C15	2.3 (3)
N2—C3—C4—N3	−158.8 (2)	C13—N4—C14—Cl	−177.37 (17)
N1—C3—C4—N3	20.8 (4)	N4—C14—C15—C16	−3.2 (3)
N2—C3—C4—C5	14.3 (3)	Cl—C14—C15—C16	176.44 (17)
N1—C3—C4—C5	−166.1 (2)	C14—C15—C16—C12	0.6 (3)
N3—C4—C5—C6	−173.1 (2)	C13—C12—C16—C15	2.4 (3)
C3—C4—C5—C6	13.5 (3)	C11—C12—C16—C15	−175.1 (2)
C4—C5—C6—C7	−48.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O3	0.97	2.35	2.803 (3)	108
C13—H13···N1	0.93	2.54	2.891 (3)	103

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O3	0.97	2.35	2.803 (3)	108
C13—H13⋯N1	0.93	2.54	2.891 (3)	103

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