5-(4-Bromo­phen­oxy)-1-methyl-3-methyl-1H-pyrazole-4-carbaldehyde-O-[(5-meth­oxy-1,3,4-thia­diazol-2-yl)-meth­yl]oxime

Fan, C.-G.; Chen, J.-C.; Dai, H.; Wei, Y.-H.; Shi, Y.-J.

doi:10.1107/S1600536812042274

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3122

doi:10.1107/S1600536812042274

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5-(4-Bromophenoxy)-1-methyl-3-methyl-1H-pyrazole-4-carbaldehyde-O-[(5-methoxy-1,3,4-thiadiazol-2-yl)-methyl]oxime

Chong-Guang Fan,^a Jian-Cun Chen,^a Hong Dai,^a ^* Yun-Hua Wei ^a and Yu-Jun Shi ^a ^*

^aCollege of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, People's Republic of China
^*Correspondence e-mail: gaofz2005@yahoo.com.cn, yjshi2001@yahoo.com.cn

(Received 7 October 2012; accepted 9 October 2012; online 13 October 2012)

In the title molecule, C₁₆H₁₆BrN₅O₃S, the 1,3,4-thiadiazole ring is situated under the benzene ring, forming a dihedral angle of 86.6 (2)°, and with an S⋯Cg (where Cg is the centroid of the benzene ring) distance of 3.312 (3) Å. The benzene and 1,3,4-thiadiazole rings form dihedral angles of 83.8 (3) and 57.7 (2)°, respectively, with the central pyrazole ring. In the absence of classical hydrogen bonds, the crystal packing is stabilized by a C—H⋯π interaction..

Related literature

For a related structure, see: Dai et al. (2011 ).

Experimental

Crystal data

C₁₆H₁₆BrN₅O₃S
M_r = 438.31
Triclinic, $[P \overline 1]$
a = 9.732 (3) Å
b = 9.832 (2) Å
c = 11.166 (3) Å
α = 64.55 (2)°
β = 69.62 (2)°
γ = 75.33 (3)°
V = 897.5 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.43 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ) T_min = 0.642, T_max = 0.759
7729 measured reflections
3175 independent reflections
2363 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.054
S = 1.02
3175 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯Cgⁱ	0.98	2.89	3.652 (4)	125
Symmetry code: (i) -x+2, -y+2, -z+2.

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; 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: 10.1107/S1600536812042274/cv5348sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812042274/cv5348Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812042274/cv5348Isup3.cml

checkCIF report

Comment top

In a continuation of our structural study of pyrazole oxime derivatives (Dai et al., 2011), we report here the crystal structure of the title compound, (I). In (I) (Fig. 1), all bonds lengths and angles are similar to those observed in the related compound (Dai et al., 2011). The dihedral angles between the substituted phenyl ring and the pyrazole ring and between the 1,3,4-thiadiazole ring and the pyrazole ring are 83.8 (3)° and 57.7 (2)°, respectively. The crystal packing displays short intermolecular C···C contacts of 3.203 (4) Å.

Related literature top

For a related structure, see: Dai et al. (2011).

Experimental top

To a stirred solution of 1-methyl-3-methyl-5-(4-bromophenoxy)-1H-pyrazole -4-carbaldehyde oxime (3 mmol), and powdered potassium carbonate (9 mmol) in 30 ml of anhydrous acetonitrile, was added 2-chloromethyl-5-methoxy- 1,3,4-thiadiazole (4.2 mmol) at room temperature. The mixture was heated to reflux for 13 h. After removal of the solvent, the residue was separated by column chromatography on silica gel using a mixture of petroleum ether/ethyl acetate to obtain colourless crystals.

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); 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 the atomic numbering and 50% probabilty displacement ellipsoids.

5-(4-Bromophenoxy)-1-methyl-3-methyl-1H-pyrazole-4-carbaldehyde- O-[(5-methoxy-1,3,4-thiadiazol-2-yl)-methyl]oxime top

Crystal data top

C₁₆H₁₆BrN₅O₃S	Z = 2
M_r = 438.31	F(000) = 444
Triclinic, P1	D_x = 1.622 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.732 (3) Å	Cell parameters from 3391 reflections
b = 9.832 (2) Å	θ = 2.1–27.9°
c = 11.166 (3) Å	µ = 2.43 mm⁻¹
α = 64.55 (2)°	T = 113 K
β = 69.62 (2)°	Prism, colourless
γ = 75.33 (3)°	0.20 × 0.18 × 0.12 mm
V = 897.5 (4) Å³

Data collection top

Rigaku Saturn724 CCD diffractometer	3175 independent reflections
Radiation source: rotating anode	2363 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.044
Detector resolution: 14.22 pixels mm^-1	θ_max = 25.0°, θ_min = 2.1°
ω and ϕ scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −11→11
T_min = 0.642, T_max = 0.759	l = −13→13
7729 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.054	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.P)²] where P = (F_o² + 2F_c²)/3
3175 reflections	(Δ/σ)_max = 0.001
238 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₆H₁₆BrN₅O₃S	γ = 75.33 (3)°
M_r = 438.31	V = 897.5 (4) Å³
Triclinic, P1	Z = 2
a = 9.732 (3) Å	Mo Kα radiation
b = 9.832 (2) Å	µ = 2.43 mm⁻¹
c = 11.166 (3) Å	T = 113 K
α = 64.55 (2)°	0.20 × 0.18 × 0.12 mm
β = 69.62 (2)°

Data collection top

Rigaku Saturn724 CCD diffractometer	3175 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	2363 reflections with I > 2σ(I)
T_min = 0.642, T_max = 0.759	R_int = 0.044
7729 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.054	H-atom parameters constrained
S = 1.02	Δρ_max = 0.36 e Å⁻³
3175 reflections	Δρ_min = −0.49 e Å⁻³
238 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
Br1	0.51369 (3)	0.66558 (3)	1.32176 (3)	0.02651 (10)
S1	0.54286 (8)	0.73735 (8)	0.87231 (7)	0.02150 (19)
O1	0.96309 (18)	0.88211 (18)	0.76885 (17)	0.0166 (5)
O2	0.63830 (19)	0.93453 (19)	0.53541 (18)	0.0202 (5)
O3	0.3297 (2)	0.6561 (2)	1.10298 (18)	0.0291 (5)
N1	1.0439 (2)	1.1205 (2)	0.6791 (2)	0.0157 (5)
N2	1.0308 (2)	1.2623 (2)	0.5802 (2)	0.0173 (6)
N3	0.7358 (2)	0.9392 (2)	0.6035 (2)	0.0166 (5)
N4	0.3648 (2)	0.7120 (2)	0.7625 (2)	0.0196 (6)
N5	0.2883 (2)	0.6764 (2)	0.9015 (2)	0.0202 (6)
C1	0.6530 (3)	0.7382 (3)	1.1473 (3)	0.0174 (7)
C2	0.6437 (3)	0.8902 (3)	1.0675 (3)	0.0161 (7)
H2	0.5676	0.9587	1.0999	0.019*
C3	0.7454 (3)	0.9447 (3)	0.9390 (3)	0.0155 (7)
H3	0.7395	1.0497	0.8827	0.019*
C4	0.8547 (3)	0.8423 (3)	0.8958 (3)	0.0143 (6)
C5	0.8662 (3)	0.6893 (3)	0.9768 (3)	0.0168 (7)
H5	0.9440	0.6213	0.9455	0.020*
C6	0.7646 (3)	0.6357 (3)	1.1029 (3)	0.0176 (7)
H6	0.7705	0.5305	1.1587	0.021*
C7	0.9571 (3)	1.0319 (3)	0.6821 (3)	0.0144 (7)
C8	0.8804 (3)	1.1148 (3)	0.5847 (3)	0.0114 (6)
C9	0.9324 (3)	1.2589 (3)	0.5235 (3)	0.0150 (7)
C10	0.8892 (3)	1.3946 (3)	0.4084 (2)	0.0211 (7)
H10A	0.9228	1.4843	0.4016	0.032*
H10B	0.7816	1.4105	0.4264	0.032*
H10C	0.9350	1.3784	0.3216	0.032*
C11	1.1437 (3)	1.0799 (3)	0.7631 (3)	0.0239 (7)
H11A	1.1112	1.1413	0.8199	0.036*
H11B	1.2437	1.0986	0.7032	0.036*
H11C	1.1436	0.9721	0.8229	0.036*
C12	0.7799 (3)	1.0706 (3)	0.5427 (3)	0.0153 (6)
H12	0.7448	1.1421	0.4664	0.018*
C13	0.5995 (3)	0.7852 (3)	0.5917 (3)	0.0194 (7)
H13A	0.6904	0.7119	0.5950	0.023*
H13B	0.5533	0.7753	0.5301	0.023*
C14	0.4958 (3)	0.7459 (3)	0.7328 (3)	0.0151 (6)
C15	0.3691 (3)	0.6834 (3)	0.9682 (3)	0.0194 (7)
C16	0.1869 (3)	0.6019 (3)	1.1781 (3)	0.0360 (9)
H16A	0.1105	0.6772	1.1391	0.054*
H16B	0.1657	0.5860	1.2754	0.054*
H16C	0.1879	0.5058	1.1708	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02695 (19)	0.03281 (19)	0.01571 (17)	−0.00625 (14)	−0.00270 (14)	−0.00650 (15)
S1	0.0216 (4)	0.0264 (4)	0.0212 (4)	−0.0059 (4)	−0.0073 (3)	−0.0105 (4)
O1	0.0170 (11)	0.0132 (10)	0.0140 (11)	0.0018 (8)	−0.0045 (8)	−0.0019 (9)
O2	0.0230 (12)	0.0190 (11)	0.0215 (11)	−0.0089 (9)	−0.0136 (9)	−0.0009 (10)
O3	0.0335 (13)	0.0366 (13)	0.0201 (12)	−0.0128 (11)	−0.0003 (10)	−0.0140 (11)
N1	0.0149 (14)	0.0174 (13)	0.0178 (13)	−0.0006 (11)	−0.0085 (11)	−0.0070 (11)
N2	0.0196 (14)	0.0154 (13)	0.0160 (13)	−0.0016 (11)	−0.0063 (11)	−0.0044 (11)
N3	0.0142 (13)	0.0213 (13)	0.0184 (13)	−0.0059 (11)	−0.0091 (11)	−0.0056 (12)
N4	0.0185 (14)	0.0196 (13)	0.0202 (14)	−0.0064 (11)	−0.0067 (11)	−0.0036 (12)
N5	0.0190 (15)	0.0195 (14)	0.0211 (14)	−0.0057 (11)	−0.0055 (11)	−0.0050 (12)
C1	0.0212 (17)	0.0228 (16)	0.0088 (15)	−0.0060 (14)	−0.0058 (13)	−0.0034 (14)
C2	0.0157 (16)	0.0167 (15)	0.0195 (17)	0.0050 (13)	−0.0105 (13)	−0.0095 (14)
C3	0.0175 (16)	0.0106 (14)	0.0180 (16)	0.0011 (13)	−0.0096 (13)	−0.0030 (13)
C4	0.0155 (16)	0.0176 (15)	0.0121 (15)	−0.0018 (13)	−0.0075 (12)	−0.0049 (13)
C5	0.0168 (16)	0.0161 (15)	0.0170 (16)	0.0052 (13)	−0.0087 (13)	−0.0066 (13)
C6	0.0220 (17)	0.0134 (15)	0.0184 (16)	0.0020 (13)	−0.0130 (13)	−0.0034 (14)
C7	0.0130 (16)	0.0143 (15)	0.0139 (15)	−0.0015 (13)	−0.0012 (12)	−0.0057 (13)
C8	0.0103 (16)	0.0103 (14)	0.0130 (15)	−0.0014 (12)	−0.0040 (12)	−0.0031 (13)
C9	0.0132 (16)	0.0184 (15)	0.0110 (15)	0.0002 (13)	−0.0023 (13)	−0.0054 (13)
C10	0.0225 (17)	0.0156 (15)	0.0202 (17)	−0.0059 (13)	−0.0059 (14)	−0.0003 (14)
C11	0.0274 (19)	0.0275 (18)	0.0245 (17)	−0.0033 (15)	−0.0169 (14)	−0.0091 (15)
C12	0.0100 (16)	0.0194 (16)	0.0137 (16)	0.0028 (13)	−0.0055 (12)	−0.0043 (14)
C13	0.0216 (17)	0.0196 (16)	0.0213 (17)	−0.0060 (14)	−0.0097 (14)	−0.0067 (14)
C14	0.0198 (17)	0.0106 (14)	0.0219 (17)	−0.0005 (13)	−0.0105 (13)	−0.0096 (13)
C15	0.0218 (18)	0.0133 (15)	0.0204 (17)	−0.0033 (13)	−0.0021 (14)	−0.0061 (14)
C16	0.034 (2)	0.039 (2)	0.0244 (19)	−0.0063 (17)	0.0040 (16)	−0.0103 (17)

Geometric parameters (Å, º) top

Br1—C1	1.897 (2)	C3—H3	0.9500
S1—C15	1.730 (3)	C4—C5	1.381 (3)
S1—C14	1.735 (3)	C5—C6	1.376 (3)
O1—C7	1.371 (3)	C5—H5	0.9500
O1—C4	1.402 (3)	C6—H6	0.9500
O2—C13	1.420 (3)	C7—C8	1.378 (3)
O2—N3	1.426 (3)	C8—C9	1.422 (3)
O3—C15	1.337 (3)	C8—C12	1.442 (3)
O3—C16	1.449 (3)	C9—C10	1.492 (3)
N1—C7	1.342 (3)	C10—H10A	0.9800
N1—N2	1.365 (3)	C10—H10B	0.9800
N1—C11	1.448 (3)	C10—H10C	0.9800
N2—C9	1.333 (3)	C11—H11A	0.9800
N3—C12	1.279 (3)	C11—H11B	0.9800
N4—C14	1.293 (3)	C11—H11C	0.9800
N4—N5	1.395 (3)	C12—H12	0.9500
N5—C15	1.287 (3)	C13—C14	1.489 (3)
C1—C2	1.370 (3)	C13—H13A	0.9900
C1—C6	1.393 (3)	C13—H13B	0.9900
C2—C3	1.395 (3)	C16—H16A	0.9800
C2—H2	0.9500	C16—H16B	0.9800
C3—C4	1.376 (3)	C16—H16C	0.9800

C15—S1—C14	85.62 (13)	N2—C9—C10	121.1 (2)
C7—O1—C4	117.5 (2)	C8—C9—C10	127.0 (3)
C13—O2—N3	109.17 (19)	C9—C10—H10A	109.5
C15—O3—C16	114.5 (2)	C9—C10—H10B	109.5
C7—N1—N2	111.0 (2)	H10A—C10—H10B	109.5
C7—N1—C11	127.8 (2)	C9—C10—H10C	109.5
N2—N1—C11	121.2 (2)	H10A—C10—H10C	109.5
C9—N2—N1	105.0 (2)	H10B—C10—H10C	109.5
C12—N3—O2	108.0 (2)	N1—C11—H11A	109.5
C14—N4—N5	113.1 (2)	N1—C11—H11B	109.5
C15—N5—N4	110.5 (2)	H11A—C11—H11B	109.5
C2—C1—C6	121.0 (2)	N1—C11—H11C	109.5
C2—C1—Br1	119.8 (2)	H11A—C11—H11C	109.5
C6—C1—Br1	119.2 (2)	H11B—C11—H11C	109.5
C1—C2—C3	120.2 (2)	N3—C12—C8	122.9 (3)
C1—C2—H2	119.9	N3—C12—H12	118.5
C3—C2—H2	119.9	C8—C12—H12	118.5
C4—C3—C2	118.3 (2)	O2—C13—C14	112.9 (2)
C4—C3—H3	120.8	O2—C13—H13A	109.0
C2—C3—H3	120.8	C14—C13—H13A	109.0
C3—C4—C5	121.7 (2)	O2—C13—H13B	109.0
C3—C4—O1	124.0 (2)	C14—C13—H13B	109.0
C5—C4—O1	114.3 (2)	H13A—C13—H13B	107.8
C6—C5—C4	119.8 (3)	N4—C14—C13	123.1 (2)
C6—C5—H5	120.1	N4—C14—S1	114.4 (2)
C4—C5—H5	120.1	C13—C14—S1	122.53 (19)
C5—C6—C1	118.9 (2)	N5—C15—O3	126.0 (2)
C5—C6—H6	120.5	N5—C15—S1	116.3 (2)
C1—C6—H6	120.5	O3—C15—S1	117.6 (2)
N1—C7—O1	119.3 (3)	O3—C16—H16A	109.5
N1—C7—C8	109.1 (2)	O3—C16—H16B	109.5
O1—C7—C8	131.5 (2)	H16A—C16—H16B	109.5
C7—C8—C9	103.0 (2)	O3—C16—H16C	109.5
C7—C8—C12	130.8 (2)	H16A—C16—H16C	109.5
C9—C8—C12	126.0 (3)	H16B—C16—H16C	109.5
N2—C9—C8	111.9 (2)

C7—N1—N2—C9	0.7 (3)	N1—C7—C8—C12	176.5 (2)
C11—N1—N2—C9	179.4 (2)	O1—C7—C8—C12	0.4 (5)
C13—O2—N3—C12	174.10 (19)	N1—N2—C9—C8	−0.1 (3)
C14—N4—N5—C15	−1.2 (3)	N1—N2—C9—C10	−179.3 (2)
C6—C1—C2—C3	0.8 (4)	C7—C8—C9—N2	−0.5 (3)
Br1—C1—C2—C3	−179.91 (19)	C12—C8—C9—N2	−176.4 (2)
C1—C2—C3—C4	−0.4 (4)	C7—C8—C9—C10	178.7 (2)
C2—C3—C4—C5	−0.7 (4)	C12—C8—C9—C10	2.8 (4)
C2—C3—C4—O1	179.6 (2)	O2—N3—C12—C8	−179.9 (2)
C7—O1—C4—C3	−1.3 (4)	C7—C8—C12—N3	6.2 (4)
C7—O1—C4—C5	179.0 (2)	C9—C8—C12—N3	−179.1 (2)
C3—C4—C5—C6	1.4 (4)	N3—O2—C13—C14	72.8 (3)
O1—C4—C5—C6	−178.9 (2)	N5—N4—C14—C13	178.9 (2)
C4—C5—C6—C1	−1.1 (4)	N5—N4—C14—S1	0.4 (3)
C2—C1—C6—C5	0.0 (4)	O2—C13—C14—N4	118.3 (3)
Br1—C1—C6—C5	−179.35 (19)	O2—C13—C14—S1	−63.3 (3)
N2—N1—C7—O1	175.63 (19)	C15—S1—C14—N4	0.4 (2)
C11—N1—C7—O1	−3.0 (4)	C15—S1—C14—C13	−178.2 (2)
N2—N1—C7—C8	−1.0 (3)	N4—N5—C15—O3	179.9 (2)
C11—N1—C7—C8	−179.6 (2)	N4—N5—C15—S1	1.5 (3)
C4—O1—C7—N1	98.1 (3)	C16—O3—C15—N5	5.5 (4)
C4—O1—C7—C8	−86.2 (3)	C16—O3—C15—S1	−176.12 (18)
N1—C7—C8—C9	0.9 (3)	C14—S1—C15—N5	−1.1 (2)
O1—C7—C8—C9	−175.2 (2)	C14—S1—C15—O3	−179.7 (2)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···Cgⁱ	0.98	2.89	3.652 (4)	125

Symmetry code: (i) −x+2, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆BrN₅O₃S
M_r	438.31
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	9.732 (3), 9.832 (2), 11.166 (3)
α, β, γ (°)	64.55 (2), 69.62 (2), 75.33 (3)
V (Å³)	897.5 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.43
Crystal size (mm)	0.20 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku Saturn724 CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2008)
T_min, T_max	0.642, 0.759
No. of measured, independent and observed [I > 2σ(I)] reflections	7729, 3175, 2363
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.054, 1.02
No. of reflections	3175
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.49

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···Cgⁱ	0.98	2.89	3.652 (4)	125

Symmetry code: (i) −x+2, −y+2, −z+2.

Acknowledgements

This work was supported by the Science and Technology Projects Fund of Nantong City (Nos. K2010016, AS2010005 and AS2011011), the Science Foundation of Nantong University (grant No. 11Z046) and the Science Foundation of Nantong University Xinglin College (grant No. 2010 K132).

References

Dai, H., Miao, W.-K., Wu, S.-S., Qin, X. & Fang, J.-X. (2011). Acta Cryst. E67, o775. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (2008). CrystalClear. Rigaku Corporation, Toyko, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 11| November 2012| Page o3122

doi:10.1107/S1600536812042274

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

5-(4-Bromo­phen­­oxy)-1-methyl-3-methyl-1H-pyrazole-4-carbaldehyde-O-[(5-meth­­oxy-1,3,4-thia­diazol-2-yl)-meth­yl]oxime

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5-(4-Bromophenoxy)-1-methyl-3-methyl-1H-pyrazole-4-carbaldehyde-O-[(5-methoxy-1,3,4-thiadiazol-2-yl)-methyl]oxime