Ethyl 5-{[(E)-2-(isonicotinoyl)hydrazinyl­idene]methyl}-3,4-dimethyl-1H-pyrrole-2-carboxyl­ate dihydrate

Zhang, Z.-P.; Wang, Y.; Lu, M.-J.; Jia, L.-W.; Qiao, H.-C.

doi:10.1107/S1600536811017132

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1413

doi:10.1107/S1600536811017132

Open

access

Ethyl 5-{[(E)-2-(isonicotinoyl)hydrazinylidene]methyl}-3,4-dimethyl-1H-pyrrole-2-carboxylate dihydrate

Zhao-Po Zhang,^a Yuan Wang,^a ^* Ming-Jia Lu,^a Lei-Wei Jia ^a and Hong-Chang Qiao ^a

^aDepartment of Physics and Chemistry, Henan Polytechnic University, Jiaozuo 454000, People's Republic of China
^*Correspondence e-mail: wangyuan08@hpu.edu.cn

(Received 27 April 2011; accepted 6 May 2011; online 14 May 2011)

In the title compound, C₁₆H₁₈N₄O₃·2H₂O, the dihedral angle between the pyrrole and pyridine rings in the hydrazone molecule is 7.12 (3)°. In the crystal structure, intermolecular N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds link the hydrazone and water molecules into double layers parallel to (101). The crystal packing exhibits weak π–π interactions between the pyrrole and pyridine rings of neighbouring hydrazone molecules [centroid–centroid distance = 3.777 (3) Å]. The crystal studied was a non-merohedral twin, the refined ratio of twin domains being 0.73 (3):0.27 (3).

Related literature

For the antioxidant and DNA-binding properties of hydrazone complexes, see: Liu & Yang (2009 ). For the synthesis and structure of 5-formyl-3,4-dimethyl-1H-pyrrole-2-carboxylate, see: Wu et al. (2009 ). For the similar structure of ethyl 5-[(3,4-dimethyl-1H-pyrrole-2-carboxylimino)-methyl]-3,4-dimethyl-1H-pyrrole-2-carboxylate monohydrate, see: Wang et al. (2009 ).

Experimental

Crystal data

C₁₆H₁₈N₄O₃·2H₂O
M_r = 350.38
Monoclinic, P 2₁ /n
a = 8.297 (4) Å
b = 18.120 (6) Å
c = 11.834 (4) Å
β = 91.814 (4)°
V = 1778.3 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.23 × 0.21 × 0.16 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.977, T_max = 0.984
10998 measured reflections
3839 independent reflections
2671 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.074
wR(F²) = 0.176
S = 1.02
3839 reflections
241 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1Wⁱ	0.86	2.08	2.919 (4)	164
N4—H4A⋯O2W	0.86	2.24	3.084 (4)	165
O1W—H1C⋯N1	0.69 (5)	2.18 (5)	2.854 (4)	164 (6)
O1W—H1D⋯O2Wⁱⁱ	0.91 (5)	1.88 (5)	2.790 (5)	174 (5)
O2W—H2C⋯O2ⁱⁱⁱ	0.92 (5)	2.06 (5)	2.941 (4)	160 (4)
O2W—H2D⋯O1	0.82 (5)	2.27 (5)	3.048 (4)	159 (5)
O2W—H2D⋯N3	0.82 (5)	2.43 (5)	3.014 (4)	129 (4)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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 I, global. DOI: 10.1107/S1600536811017132/cv5084sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017132/cv5084Isup2.hkl

checkCIF report

Comment top

In recent years, hydrazone complexes have received extensive attention due to their biological and pharmaceutical activities (Liu et al., 2009). As a part of our studies of hydrazone ligands bearing pyrrole unit (Wang et al., 2009), we present here the crystal structure of the title compound.

In the title compound (Fig. 1), the imine C=N double bond has an E configuration. The dihedral angle between pyrrole (N4/C8–C11, r.m.s. deviation 0.0030 Å) and pyridine rings (N1/C1–C5, r.m.s. deviation 0.0038 Å) in the hydrazone molecule is 7.12 (3)°. In the crystal structure, intermolecular N—H···O, O—H···N and O—H···O hydrogen bonds link the hydrazone and water molecules into doubled layers parallel to (101) plane. The crystal packing exhibits weak π–π interactions between the pyrrole and pyridine rings from the neighbouring hydrazone molecules [centroid-to-centroid distance of 3.777 (3) Å].

Related literature top

For the antioxidant and DNA-binding properties of hydrazone complexes, see: Liu & Yang (2009). For the synthesis and structure of 5-formyl-3,4-dimethyl-1H-pyrrole-2-carboxylate, see: Wu et al. (2009). For the similar structure of ethyl 5-[(3,4-dimethyl-1H-pyrrole-2-carboxylimino)-methyl]-3,4-dimethyl-1H-pyrrole-2-carboxylate monohydrate, see: Wang et al. (2009).

Experimental top

Isonicotinohydrazide (0.137 g, 1 mmol) and ethyl 5-formyl-3,4-dimethyl-1H-pyrrole-2-carboxylate (0.167 g, 1 mmol) (Wu et al., 2009) was dissolved in an ethanol solution. The mixture was stirred for 4 h at room temperture. The resulting solution was left in air for a few days, yielding yellow prism-shaped crystals.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 title compound with the displacement ellipsoids shown at the 50% probability level.

Ethyl 5-{[(E)-2-(isonicotinoyl)hydrazinylidene]methyl}- 3,4-dimethyl-1H-pyrrole-2-carboxylate dihydrate top

Crystal data top

C₁₆H₁₈N₄O₃·2H₂O	F(000) = 744
M_r = 350.38	D_x = 1.309 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.297 (4) Å	θ = 2.7–25.3°
b = 18.120 (6) Å	µ = 0.10 mm⁻¹
c = 11.834 (4) Å	T = 296 K
β = 91.814 (4)°	Prism, yellow
V = 1778.3 (11) Å³	0.23 × 0.21 × 0.16 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	3839 independent reflections
Radiation source: fine-focus sealed tube	2671 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ϕ and ω scans	θ_max = 27.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→10
T_min = 0.977, T_max = 0.984	k = −9→24
10998 measured reflections	l = −15→15

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.176	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.02P)² + 3.5P] where P = (F_o² + 2F_c²)/3
3839 reflections	(Δ/σ)_max = 0.069
241 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₆H₁₈N₄O₃·2H₂O	V = 1778.3 (11) Å³
M_r = 350.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.297 (4) Å	µ = 0.10 mm⁻¹
b = 18.120 (6) Å	T = 296 K
c = 11.834 (4) Å	0.23 × 0.21 × 0.16 mm
β = 91.814 (4)°

Data collection top

Bruker SMART APEX CCD diffractometer	3839 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2671 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.984	R_int = 0.037
10998 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.074	0 restraints
wR(F²) = 0.176	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.41 e Å⁻³
3839 reflections	Δρ_min = −0.27 e Å⁻³
241 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
O1	0.6319 (3)	0.46189 (12)	0.4160 (2)	0.0530 (6)
O2	1.1091 (4)	0.29040 (14)	0.9756 (2)	0.0660 (8)
O3	0.9696 (3)	0.27423 (12)	0.8122 (2)	0.0564 (7)
N1	0.4775 (4)	0.68078 (16)	0.1780 (2)	0.0532 (8)
N2	0.7766 (3)	0.55247 (14)	0.5019 (2)	0.0406 (6)
H2A	0.8043	0.5982	0.5024	0.049*
N3	0.8374 (3)	0.50452 (14)	0.5828 (2)	0.0420 (6)
N4	0.9761 (3)	0.41573 (14)	0.7584 (2)	0.0415 (6)
H4A	0.9158	0.3892	0.7141	0.050*
C1	0.4299 (4)	0.6106 (2)	0.1836 (3)	0.0545 (9)
H1	0.3507	0.5946	0.1319	0.065*
C2	0.4901 (4)	0.56074 (19)	0.2606 (3)	0.0498 (8)
H2	0.4522	0.5124	0.2604	0.060*
C3	0.6076 (4)	0.58255 (17)	0.3388 (3)	0.0385 (7)
C4	0.6579 (5)	0.65506 (18)	0.3348 (3)	0.0531 (9)
H4	0.7355	0.6730	0.3861	0.064*
C5	0.5898 (5)	0.70012 (19)	0.2527 (3)	0.0605 (10)
H5	0.6267	0.7485	0.2500	0.073*
C6	0.6727 (4)	0.52615 (16)	0.4219 (3)	0.0380 (7)
C7	0.9388 (4)	0.53192 (17)	0.6540 (3)	0.0418 (7)
H7A	0.9686	0.5811	0.6471	0.050*
C8	1.0084 (4)	0.48875 (17)	0.7448 (3)	0.0412 (7)
C9	1.1112 (4)	0.51125 (18)	0.8322 (3)	0.0428 (8)
C10	1.1406 (4)	0.44984 (18)	0.9021 (3)	0.0423 (7)
C11	1.0555 (4)	0.39167 (17)	0.8543 (3)	0.0411 (7)
C12	1.1778 (5)	0.5870 (2)	0.8501 (3)	0.0654 (11)
H12A	1.1754	0.6131	0.7795	0.098*
H12B	1.2870	0.5837	0.8789	0.098*
H12C	1.1137	0.6129	0.9033	0.098*
C13	1.2480 (5)	0.4481 (2)	1.0061 (3)	0.0589 (10)
H13A	1.1894	0.4654	1.0695	0.088*
H13B	1.3398	0.4792	0.9954	0.088*
H13C	1.2835	0.3984	1.0201	0.088*
C14	1.0502 (4)	0.31492 (18)	0.8893 (3)	0.0452 (8)
C15	0.9548 (5)	0.19650 (18)	0.8342 (3)	0.0609 (10)
H15A	0.8978	0.1883	0.9034	0.073*
H15B	1.0605	0.1738	0.8420	0.073*
C16	0.8642 (7)	0.1652 (2)	0.7371 (4)	0.0830 (15)
H16A	0.7623	0.1900	0.7281	0.125*
H16B	0.8461	0.1135	0.7498	0.125*
H16C	0.9247	0.1715	0.6700	0.125*
O1W	0.4291 (4)	0.80318 (15)	0.0290 (3)	0.0654 (8)
H1C	0.428 (7)	0.770 (3)	0.059 (5)	0.098*
H1D	0.528 (6)	0.813 (3)	0.001 (4)	0.098*
O2W	0.7783 (3)	0.34071 (15)	0.5656 (2)	0.0588 (7)
H2C	0.704 (6)	0.305 (3)	0.544 (4)	0.088*
H2D	0.744 (6)	0.380 (3)	0.541 (4)	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0688 (16)	0.0297 (12)	0.0598 (15)	−0.0029 (11)	−0.0066 (12)	0.0035 (10)
O2	0.102 (2)	0.0431 (14)	0.0513 (15)	0.0040 (14)	−0.0203 (15)	0.0099 (12)
O3	0.0790 (18)	0.0327 (12)	0.0562 (15)	−0.0080 (12)	−0.0160 (13)	0.0066 (11)
N1	0.0622 (19)	0.0453 (17)	0.0512 (18)	0.0079 (14)	−0.0106 (15)	0.0081 (14)
N2	0.0489 (15)	0.0314 (13)	0.0412 (15)	0.0009 (11)	−0.0045 (12)	0.0071 (11)
N3	0.0514 (16)	0.0334 (14)	0.0412 (15)	0.0061 (12)	0.0007 (12)	0.0060 (11)
N4	0.0479 (15)	0.0373 (14)	0.0388 (14)	−0.0002 (12)	−0.0063 (12)	0.0009 (11)
C1	0.055 (2)	0.056 (2)	0.051 (2)	−0.0028 (17)	−0.0150 (17)	0.0018 (17)
C2	0.053 (2)	0.0374 (18)	0.058 (2)	−0.0064 (15)	−0.0077 (17)	0.0021 (16)
C3	0.0430 (17)	0.0327 (16)	0.0396 (17)	0.0022 (13)	0.0000 (13)	−0.0006 (13)
C4	0.069 (2)	0.0373 (18)	0.052 (2)	−0.0048 (16)	−0.0192 (18)	0.0029 (15)
C5	0.079 (3)	0.0298 (18)	0.072 (3)	−0.0034 (17)	−0.017 (2)	0.0099 (17)
C6	0.0437 (17)	0.0295 (16)	0.0410 (17)	0.0023 (13)	0.0040 (14)	0.0027 (13)
C7	0.0525 (19)	0.0333 (16)	0.0396 (17)	0.0013 (14)	0.0019 (15)	0.0003 (13)
C8	0.0459 (18)	0.0379 (17)	0.0399 (17)	0.0056 (14)	0.0024 (14)	0.0016 (14)
C9	0.0515 (19)	0.0367 (17)	0.0404 (17)	0.0011 (14)	0.0029 (15)	−0.0014 (13)
C10	0.0501 (19)	0.0384 (17)	0.0383 (17)	0.0027 (14)	−0.0022 (14)	−0.0018 (14)
C11	0.0502 (18)	0.0368 (17)	0.0359 (16)	0.0040 (14)	−0.0030 (14)	0.0018 (13)
C12	0.092 (3)	0.042 (2)	0.061 (2)	−0.008 (2)	−0.011 (2)	0.0002 (18)
C13	0.072 (3)	0.056 (2)	0.047 (2)	0.0001 (19)	−0.0138 (18)	−0.0002 (17)
C14	0.057 (2)	0.0384 (18)	0.0404 (18)	0.0043 (15)	−0.0020 (15)	0.0007 (14)
C15	0.086 (3)	0.0304 (18)	0.065 (2)	−0.0057 (18)	−0.004 (2)	0.0070 (16)
C16	0.118 (4)	0.043 (2)	0.086 (3)	−0.005 (2)	−0.025 (3)	−0.005 (2)
O1W	0.0706 (18)	0.0443 (16)	0.081 (2)	0.0111 (14)	−0.0049 (16)	0.0186 (14)
O2W	0.0681 (18)	0.0384 (14)	0.0692 (18)	0.0038 (12)	−0.0093 (14)	−0.0031 (13)

Geometric parameters (Å, º) top

O1—C6	1.214 (4)	C7—H7A	0.9300
O2—C14	1.204 (4)	C8—C9	1.382 (5)
O3—C14	1.336 (4)	C9—C10	1.403 (4)
O3—C15	1.438 (4)	C9—C12	1.492 (5)
N1—C5	1.312 (5)	C10—C11	1.380 (4)
N1—C1	1.334 (5)	C10—C13	1.497 (5)
N2—C6	1.347 (4)	C11—C14	1.452 (4)
N2—N3	1.377 (3)	C12—H12A	0.9600
N2—H2A	0.8600	C12—H12B	0.9600
N3—C7	1.273 (4)	C12—H12C	0.9600
N4—C8	1.361 (4)	C13—H13A	0.9600
N4—C11	1.366 (4)	C13—H13B	0.9600
N4—H4A	0.8600	C13—H13C	0.9600
C1—C2	1.366 (5)	C15—C16	1.468 (5)
C1—H1	0.9300	C15—H15A	0.9700
C2—C3	1.380 (4)	C15—H15B	0.9700
C2—H2	0.9300	C16—H16A	0.9600
C3—C4	1.380 (4)	C16—H16B	0.9600
C3—C6	1.506 (4)	C16—H16C	0.9600
C4—C5	1.376 (5)	O1W—H1C	0.69 (5)
C4—H4	0.9300	O1W—H1D	0.91 (5)
C5—H5	0.9300	O2W—H2C	0.92 (5)
C7—C8	1.435 (4)	O2W—H2D	0.82 (5)

C14—O3—C15	117.4 (3)	C11—C10—C9	106.7 (3)
C5—N1—C1	115.2 (3)	C11—C10—C13	127.2 (3)
C6—N2—N3	118.5 (3)	C9—C10—C13	126.1 (3)
C6—N2—H2A	120.7	N4—C11—C10	108.9 (3)
N3—N2—H2A	120.7	N4—C11—C14	121.6 (3)
C7—N3—N2	115.7 (3)	C10—C11—C14	129.4 (3)
C8—N4—C11	108.5 (3)	C9—C12—H12A	109.5
C8—N4—H4A	125.8	C9—C12—H12B	109.5
C11—N4—H4A	125.8	H12A—C12—H12B	109.5
N1—C1—C2	124.1 (3)	C9—C12—H12C	109.5
N1—C1—H1	117.9	H12A—C12—H12C	109.5
C2—C1—H1	117.9	H12B—C12—H12C	109.5
C1—C2—C3	119.6 (3)	C10—C13—H13A	109.5
C1—C2—H2	120.2	C10—C13—H13B	109.5
C3—C2—H2	120.2	H13A—C13—H13B	109.5
C4—C3—C2	117.2 (3)	C10—C13—H13C	109.5
C4—C3—C6	124.5 (3)	H13A—C13—H13C	109.5
C2—C3—C6	118.3 (3)	H13B—C13—H13C	109.5
C3—C4—C5	118.1 (3)	O2—C14—O3	123.9 (3)
C3—C4—H4	120.9	O2—C14—C11	125.5 (3)
C5—C4—H4	120.9	O3—C14—C11	110.7 (3)
N1—C5—C4	125.7 (3)	O3—C15—C16	106.3 (3)
N1—C5—H5	117.1	O3—C15—H15A	110.5
C4—C5—H5	117.1	C16—C15—H15A	110.5
O1—C6—N2	123.4 (3)	O3—C15—H15B	110.5
O1—C6—C3	121.3 (3)	C16—C15—H15B	110.5
N2—C6—C3	115.3 (3)	H15A—C15—H15B	108.7
N3—C7—C8	121.7 (3)	C15—C16—H16A	109.5
N3—C7—H7A	119.2	C15—C16—H16B	109.5
C8—C7—H7A	119.2	H16A—C16—H16B	109.5
N4—C8—C9	108.5 (3)	C15—C16—H16C	109.5
N4—C8—C7	122.9 (3)	H16A—C16—H16C	109.5
C9—C8—C7	128.6 (3)	H16B—C16—H16C	109.5
C8—C9—C10	107.4 (3)	H1C—O1W—H1D	112 (5)
C8—C9—C12	126.5 (3)	H2C—O2W—H2D	107 (4)
C10—C9—C12	126.1 (3)

C6—N2—N3—C7	177.9 (3)	C7—C8—C9—C10	177.6 (3)
C5—N1—C1—C2	0.3 (6)	N4—C8—C9—C12	179.8 (3)
N1—C1—C2—C3	0.1 (6)	C7—C8—C9—C12	−1.8 (6)
C1—C2—C3—C4	0.3 (5)	C8—C9—C10—C11	0.4 (4)
C1—C2—C3—C6	−179.4 (3)	C12—C9—C10—C11	179.9 (3)
C2—C3—C4—C5	−1.0 (5)	C8—C9—C10—C13	178.8 (3)
C6—C3—C4—C5	178.7 (3)	C12—C9—C10—C13	−1.8 (6)
C1—N1—C5—C4	−1.1 (6)	C8—N4—C11—C10	−0.5 (4)
C3—C4—C5—N1	1.5 (7)	C8—N4—C11—C14	−177.4 (3)
N3—N2—C6—O1	−1.4 (5)	C9—C10—C11—N4	0.0 (4)
N3—N2—C6—C3	178.1 (3)	C13—C10—C11—N4	−178.3 (3)
C4—C3—C6—O1	−174.7 (3)	C9—C10—C11—C14	176.6 (3)
C2—C3—C6—O1	5.0 (5)	C13—C10—C11—C14	−1.7 (6)
C4—C3—C6—N2	5.8 (5)	C15—O3—C14—O2	−0.7 (5)
C2—C3—C6—N2	−174.5 (3)	C15—O3—C14—C11	179.5 (3)
N2—N3—C7—C8	178.2 (3)	N4—C11—C14—O2	−175.6 (3)
C11—N4—C8—C9	0.8 (4)	C10—C11—C14—O2	8.2 (6)
C11—N4—C8—C7	−177.7 (3)	N4—C11—C14—O3	4.3 (5)
N3—C7—C8—N4	2.6 (5)	C10—C11—C14—O3	−172.0 (3)
N3—C7—C8—C9	−175.5 (3)	C14—O3—C15—C16	−179.3 (4)
N4—C8—C9—C10	−0.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1Wⁱ	0.86	2.08	2.919 (4)	164
N4—H4A···O2W	0.86	2.24	3.084 (4)	165
O1W—H1C···N1	0.69 (5)	2.18 (5)	2.854 (4)	164 (6)
O1W—H1D···O2Wⁱⁱ	0.91 (5)	1.88 (5)	2.790 (5)	174 (5)
O2W—H2C···O2ⁱⁱⁱ	0.92 (5)	2.06 (5)	2.941 (4)	160 (4)
O2W—H2D···O1	0.82 (5)	2.27 (5)	3.048 (4)	159 (5)
O2W—H2D···N3	0.82 (5)	2.43 (5)	3.014 (4)	129 (4)

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₈N₄O₃·2H₂O
M_r	350.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	8.297 (4), 18.120 (6), 11.834 (4)
β (°)	91.814 (4)
V (Å³)	1778.3 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.23 × 0.21 × 0.16

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.977, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	10998, 3839, 2671
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.176, 1.02
No. of reflections	3839
No. of parameters	241
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.27

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), 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
N2—H2A···O1Wⁱ	0.86	2.08	2.919 (4)	164
N4—H4A···O2W	0.86	2.24	3.084 (4)	165
O1W—H1C···N1	0.69 (5)	2.18 (5)	2.854 (4)	164 (6)
O1W—H1D···O2Wⁱⁱ	0.91 (5)	1.88 (5)	2.790 (5)	174 (5)
O2W—H2C···O2ⁱⁱⁱ	0.92 (5)	2.06 (5)	2.941 (4)	160 (4)
O2W—H2D···O1	0.82 (5)	2.27 (5)	3.048 (4)	159 (5)
O2W—H2D···N3	0.82 (5)	2.43 (5)	3.014 (4)	129 (4)

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

Acknowledgements

The authors are grateful to the National Natural Science Foundation of China for financial support (grant No. 21001040).

References

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA . Google Scholar
Liu, Y.-C. & Yang, Z.-Y. (2009). J. Inorg. Biochem. 103, 1014–1022. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Y., Wu, W.-N., Zhao, R.-Q., Wang, Q.-F. & Qin, B.-F. (2009). Z. Kristallogr. New Cryst. Struct. 224, 625–626. CAS Google Scholar
Wu, W.-N., Wang, Y. & Wang, Q.-F. (2009). Acta Cryst. E65, o1661. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1413

doi:10.1107/S1600536811017132

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Ethyl 5-{[(E)-2-(isonicotinoyl)hydrazinyl­­idene]methyl}-3,4-di­methyl-1H-pyrrole-2-carboxyl­ate dihydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 5-{[(E)-2-(isonicotinoyl)hydrazinylidene]methyl}-3,4-dimethyl-1H-pyrrole-2-carboxylate dihydrate