2,6-Dichloro­benzaldehyde oxime

Bao, F.-Y.

doi:10.1107/S1600536808033217

organic compounds

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Volume 64| Part 11| November 2008| Page o2134

doi:10.1107/S1600536808033217

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2,6-Dichlorobenzaldehyde oxime

Feng-Yu Bao ^a ^*

^aDepartment of Applied Chemistry, College of Science, Henan Agricultural University, Zhengzhou 450002, People's Republic of China
^*Correspondence e-mail: bfyu2008@yahoo.com.cn

(Received 10 October 2008; accepted 13 October 2008; online 18 October 2008)

In the title compound, C₇H₅Cl₂NO, there are two molecules in the asymmetric unit. The molecules are essentially identical. Each molecule is connected to a symmetry-related molecule through an inversion center by O—H⋯N hydrogen bonds, building an R₂²(6) graph-set motif.

Related literature

For related literature, see: Xu & Jin (1999 ). For graph-set notation, see: Etter et al. (1990 ); Bernstein et al. (1995 ).

Experimental

Crystal data

C₇H₅Cl₂NO
M_r = 190.02
Triclinic, $[P \overline 1]$
a = 3.8074 (1) Å
b = 14.3712 (2) Å
c = 14.3835 (3) Å
α = 89.108 (1)°
β = 88.545 (1)°
γ = 85.296 (1)°
V = 784.04 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.76 mm⁻¹
T = 296 (2) K
0.26 × 0.24 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.818, T_max = 0.884
11107 measured reflections
3235 independent reflections
2809 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.085
S = 1.06
3235 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.82	2.14	2.854 (2)	145
O2—H2⋯N2ⁱⁱ	0.82	2.15	2.850 (2)	144
Symmetry codes: (i) -x, -y+1, -z+2; (ii) -x+1, -y+2, -z+1.

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: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033217/dn2391sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033217/dn2391Isup2.hkl

checkCIF report

Comment top

2,6-Dichlorobenzaldehyde oxime, is an important intermediate for organic synthesis(Xu & Jin,1999). As part of our task, we have synthesized the title compound (I) .

In the title compound, C₇H₆Cl₂NO, there are two molecules in the asymmetric unit. Both molecules are roughly identical, the oxime fragment is twisted with respect to the dichlorobenzene ring by 53.83 (11)° and 42.99 (14)° respectively (Fig. 1).

Each molecule is connected to its symmetry related one through inversion center by O-H···N hydrogen bonds building a R₂²(6) graph-set motif (Etter et al., 1990; Bernstein et al., 1995) (Fig. 2 and Table 1).

Related literature top

For related literature, see: Xu & Jin (1999). For graph-set notation, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental top

2,6-dichlorobenzaldehyde (1 mmol) was dissolved in anhydrous methanol, hydroxylamine hydrochloride and sodium carbonate were added to this, the mixture was stirred for 3 h at room temperature. The product was isolated and recrystallized in dichloromethane, colourless single crystals of (I) was obtained after 5 d.

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: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Partial packing view of compound ( I ), showing the formation of dimer through R₂²(6) graph set motif. H bonds are represented as dashed lines. H atoms not involved in hydrogen bonding have been omitted. [Symmetry codes: (i) -x, -y+1, -z+2; (ii) -x+1 , -y+2, -z+1.]

2,6-Dichlorobenzaldehyde oxime top

Crystal data top

C₇H₅Cl₂NO	Z = 4
M_r = 190.02	F(000) = 384
Triclinic, P1	D_x = 1.610 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 3.8074 (1) Å	Cell parameters from 5529 reflections
b = 14.3712 (2) Å	θ = 2.8–27.4°
c = 14.3835 (3) Å	µ = 0.76 mm⁻¹
α = 89.108 (1)°	T = 296 K
β = 88.545 (1)°	Block, colourless
γ = 85.296 (1)°	0.26 × 0.24 × 0.16 mm
V = 784.04 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3235 independent reflections
Radiation source: fine-focus sealed tube	2809 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ω scans	θ_max = 26.5°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −4→4
T_min = 0.818, T_max = 0.884	k = −17→17
11107 measured reflections	l = −18→18

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0352P)² + 0.3155P] where P = (F_o² + 2F_c²)/3
3235 reflections	(Δ/σ)_max = 0.001
201 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₇H₅Cl₂NO	γ = 85.296 (1)°
M_r = 190.02	V = 784.04 (3) Å³
Triclinic, P1	Z = 4
a = 3.8074 (1) Å	Mo Kα radiation
b = 14.3712 (2) Å	µ = 0.76 mm⁻¹
c = 14.3835 (3) Å	T = 296 K
α = 89.108 (1)°	0.26 × 0.24 × 0.16 mm
β = 88.545 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3235 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2809 reflections with I > 2σ(I)
T_min = 0.818, T_max = 0.884	R_int = 0.018
11107 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.06	Δρ_max = 0.40 e Å⁻³
3235 reflections	Δρ_min = −0.31 e Å⁻³
201 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Cl1	0.16981 (16)	0.12516 (3)	1.04669 (4)	0.06328 (16)
Cl2	−0.28140 (15)	0.39071 (3)	0.79443 (4)	0.05813 (16)
N1	−0.0849 (4)	0.39836 (10)	0.99884 (10)	0.0430 (3)
O1	−0.2185 (4)	0.44211 (9)	1.07941 (9)	0.0574 (4)
H1	−0.1779	0.4973	1.0774	0.086*
C1	−0.0441 (4)	0.25470 (11)	0.91699 (11)	0.0371 (4)
C2	0.1056 (5)	0.16371 (12)	0.93282 (13)	0.0426 (4)
C3	0.2132 (6)	0.10360 (13)	0.86200 (16)	0.0551 (5)
H3	0.3128	0.0437	0.8752	0.066*
C4	0.1703 (7)	0.13390 (15)	0.77145 (16)	0.0653 (6)
H4	0.2431	0.0943	0.7229	0.078*
C5	0.0202 (6)	0.22243 (15)	0.75209 (14)	0.0599 (5)
H5	−0.0105	0.2422	0.6908	0.072*
C6	−0.0839 (5)	0.28136 (12)	0.82397 (13)	0.0434 (4)
C7	−0.1573 (5)	0.31429 (12)	0.99624 (12)	0.0416 (4)
H7	−0.2847	0.2895	1.0454	0.050*
Cl3	0.60840 (16)	0.62545 (3)	0.44764 (4)	0.06139 (16)
Cl4	0.35612 (19)	0.88605 (4)	0.71520 (4)	0.07117 (19)
N2	0.4237 (4)	0.89871 (10)	0.50330 (10)	0.0429 (3)
O2	0.2629 (4)	0.94385 (9)	0.42708 (9)	0.0538 (3)
H2	0.3079	0.9987	0.4256	0.081*
C8	0.5024 (4)	0.75283 (11)	0.58413 (11)	0.0384 (4)
C9	0.6303 (5)	0.66160 (12)	0.56212 (13)	0.0421 (4)
C10	0.7785 (5)	0.59945 (13)	0.62661 (16)	0.0546 (5)
H10	0.8605	0.5393	0.6093	0.065*
C11	0.8035 (6)	0.62748 (15)	0.71651 (16)	0.0618 (6)
H11	0.9070	0.5864	0.7604	0.074*
C12	0.6773 (6)	0.71567 (15)	0.74256 (14)	0.0612 (6)
H12	0.6931	0.7340	0.8039	0.073*
C13	0.5265 (5)	0.77725 (12)	0.67727 (13)	0.0477 (4)
C14	0.3507 (5)	0.81491 (11)	0.51094 (12)	0.0406 (4)
H14	0.1973	0.7919	0.4693	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0848 (4)	0.0441 (3)	0.0602 (3)	0.0013 (2)	−0.0151 (3)	0.0096 (2)
Cl2	0.0817 (4)	0.0398 (3)	0.0525 (3)	0.0009 (2)	−0.0155 (2)	0.0047 (2)
N1	0.0565 (9)	0.0348 (7)	0.0375 (8)	−0.0012 (6)	−0.0006 (6)	−0.0057 (6)
O1	0.0891 (11)	0.0393 (7)	0.0429 (7)	−0.0001 (7)	0.0089 (7)	−0.0099 (6)
C1	0.0395 (9)	0.0296 (8)	0.0428 (9)	−0.0062 (6)	−0.0018 (7)	−0.0032 (7)
C2	0.0440 (10)	0.0329 (8)	0.0514 (10)	−0.0052 (7)	−0.0040 (8)	−0.0010 (7)
C3	0.0587 (12)	0.0330 (9)	0.0729 (14)	0.0009 (8)	0.0011 (10)	−0.0095 (9)
C4	0.0859 (16)	0.0477 (12)	0.0617 (13)	−0.0014 (11)	0.0098 (12)	−0.0206 (10)
C5	0.0861 (16)	0.0497 (11)	0.0445 (11)	−0.0080 (10)	0.0018 (10)	−0.0081 (9)
C6	0.0516 (10)	0.0331 (8)	0.0462 (10)	−0.0065 (7)	−0.0038 (8)	−0.0026 (7)
C7	0.0480 (10)	0.0349 (9)	0.0417 (9)	−0.0035 (7)	0.0023 (7)	0.0002 (7)
Cl3	0.0811 (4)	0.0450 (3)	0.0574 (3)	0.0006 (2)	0.0000 (3)	−0.0139 (2)
Cl4	0.1140 (5)	0.0476 (3)	0.0511 (3)	−0.0031 (3)	0.0111 (3)	−0.0128 (2)
N2	0.0526 (9)	0.0351 (7)	0.0403 (8)	−0.0002 (6)	−0.0031 (6)	0.0031 (6)
O2	0.0744 (9)	0.0380 (7)	0.0486 (7)	0.0001 (6)	−0.0127 (7)	0.0071 (6)
C8	0.0419 (9)	0.0317 (8)	0.0422 (9)	−0.0069 (7)	0.0001 (7)	0.0022 (7)
C9	0.0444 (10)	0.0337 (8)	0.0488 (10)	−0.0068 (7)	−0.0008 (8)	−0.0002 (7)
C10	0.0569 (12)	0.0343 (9)	0.0728 (14)	−0.0048 (8)	−0.0082 (10)	0.0080 (9)
C11	0.0744 (15)	0.0481 (11)	0.0644 (13)	−0.0124 (10)	−0.0206 (11)	0.0208 (10)
C12	0.0871 (16)	0.0552 (12)	0.0443 (11)	−0.0219 (11)	−0.0113 (10)	0.0082 (9)
C13	0.0630 (12)	0.0371 (9)	0.0441 (10)	−0.0105 (8)	0.0017 (8)	−0.0001 (7)
C14	0.0451 (10)	0.0346 (9)	0.0422 (9)	−0.0027 (7)	−0.0020 (7)	−0.0020 (7)

Geometric parameters (Å, º) top

Cl1—C2	1.7376 (19)	Cl3—C9	1.7403 (19)
Cl2—C6	1.7370 (18)	Cl4—C13	1.7336 (19)
N1—C7	1.262 (2)	N2—C14	1.261 (2)
N1—O1	1.3919 (19)	N2—O2	1.3945 (18)
O1—H1	0.8200	O2—H2	0.8200
C1—C6	1.394 (2)	C8—C13	1.397 (2)
C1—C2	1.401 (2)	C8—C9	1.399 (2)
C1—C7	1.471 (2)	C8—C14	1.468 (2)
C2—C3	1.378 (3)	C9—C10	1.377 (3)
C3—C4	1.376 (3)	C10—C11	1.368 (3)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.379 (3)	C11—C12	1.372 (3)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.376 (3)	C12—C13	1.383 (3)
C5—H5	0.9300	C12—H12	0.9300
C7—H7	0.9300	C14—H14	0.9300

C7—N1—O1	111.93 (15)	C14—N2—O2	111.98 (15)
N1—O1—H1	109.5	N2—O2—H2	109.5
C6—C1—C2	115.78 (16)	C13—C8—C9	115.73 (16)
C6—C1—C7	124.33 (15)	C13—C8—C14	124.76 (16)
C2—C1—C7	119.86 (15)	C9—C8—C14	119.50 (15)
C3—C2—C1	123.02 (18)	C10—C9—C8	122.98 (18)
C3—C2—Cl1	118.10 (15)	C10—C9—Cl3	118.38 (15)
C1—C2—Cl1	118.86 (14)	C8—C9—Cl3	118.63 (14)
C4—C3—C2	118.71 (18)	C11—C10—C9	119.02 (19)
C4—C3—H3	120.6	C11—C10—H10	120.5
C2—C3—H3	120.6	C9—C10—H10	120.5
C3—C4—C5	120.56 (19)	C10—C11—C12	120.62 (19)
C3—C4—H4	119.7	C10—C11—H11	119.7
C5—C4—H4	119.7	C12—C11—H11	119.7
C6—C5—C4	119.7 (2)	C11—C12—C13	119.8 (2)
C6—C5—H5	120.2	C11—C12—H12	120.1
C4—C5—H5	120.2	C13—C12—H12	120.1
C5—C6—C1	122.23 (17)	C12—C13—C8	121.80 (18)
C5—C6—Cl2	117.14 (15)	C12—C13—Cl4	117.71 (16)
C1—C6—Cl2	120.61 (13)	C8—C13—Cl4	120.46 (14)
N1—C7—C1	121.30 (16)	N2—C14—C8	121.45 (16)
N1—C7—H7	119.4	N2—C14—H14	119.3
C1—C7—H7	119.4	C8—C14—H14	119.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.82	2.14	2.854 (2)	145
O2—H2···N2ⁱⁱ	0.82	2.15	2.850 (2)	144

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

Experimental details

Crystal data
Chemical formula	C₇H₅Cl₂NO
M_r	190.02
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	3.8074 (1), 14.3712 (2), 14.3835 (3)
α, β, γ (°)	89.108 (1), 88.545 (1), 85.296 (1)
V (Å³)	784.04 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.26 × 0.24 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.818, 0.884
No. of measured, independent and observed [I > 2σ(I)] reflections	11107, 3235, 2809
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.085, 1.06
No. of reflections	3235
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.31

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.82	2.14	2.854 (2)	145.0
O2—H2···N2ⁱⁱ	0.82	2.15	2.850 (2)	143.6

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

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, J. & Jin, S. (1999). Acta Cryst. C55, 1579–1581. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2134

doi:10.1107/S1600536808033217

Open

access