4-Meth-oxy-benzaldehyde (5-bromo-pyrimidin-2-yl)hydrazone monohydrate.

In the title Schiff base compound, C(12)H(11)BrN(4)O·H(2)O, the organic mol-ecule exists in an E configuration with respect to the C=N double bond. The pyrimidine ring is approximately planar, with a maximum deviation of 0.011 (2) Å, and forms a dihedral angle of 10.68 (8)° with the benzene ring. In the crystal, inter-molecular O-H⋯N, N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into a two-dimensional network parallel to the ac plane.

Related literature

For the preparation of hydrazones, see: Pasha & Nanjundaswamy (2004 ▶). For the importance and biological activity of hydrazones, see: Sridhar & Perumal (2003 ▶); Rollas et al. (2002 ▶); Terzioglu & Gürsoy (2003 ▶). For the biological activity of pyrimidines and their derivatives, see: Ghorab et al. (2004 ▶). For a related structure, see: Zhang et al. (2009 ▶). For reference bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C12H11BrN4O·H2O

M = 325.17

Orthorhombic,

a = 13.0606 (3) Å

b = 60.5887 (10) Å

c = 6.5618 (1) Å

V = 5192.52 (17) Å3

Z = 16

Mo Kα radiation

μ = 3.17 mm−1

T = 100 K

0.40 × 0.34 × 0.21 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.365, T max = 0.558

12616 measured reflections

4593 independent reflections

4107 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.052

S = 0.92

4593 reflections

225 parameters

1 restraint

All H-atom parameters refined

Δρmax = 0.43 e Å−3

Δρmin = −0.40 e Å−3

Absolute structure: Flack (1983 ▶), 2037 Friedel pairs

Flack parameter: 0.012 (5)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033283/wn2404sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033283/wn2404Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H11BrN4O·H2O	F(000) = 2624
Mr = 325.17	Dx = 1.664 Mg m−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 5163 reflections
a = 13.0606 (3) Å	θ = 3.7–32.2°
b = 60.5887 (10) Å	µ = 3.17 mm−1
c = 6.5618 (1) Å	T = 100 K
V = 5192.52 (17) Å3	Block, colourless
Z = 16	0.40 × 0.34 × 0.21 mm

Bruker SMART APEXII CCD area-detector diffractometer	4593 independent reflections
Radiation source: fine-focus sealed tube	4107 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 32.8°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→19
Tmin = 0.365, Tmax = 0.558	k = −92→91
12616 measured reflections	l = −9→9

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)] = 0.026	All H-atom parameters refined
wR(F2) = 0.052	w = 1/[σ2(Fo2) + (0.P)2] where P = (Fo2 + 2Fc2)/3
S = 0.92	(Δ/σ)max < 0.001
4593 reflections	Δρmax = 0.43 e Å−3
225 parameters	Δρmin = −0.40 e Å−3
1 restraint	Absolute structure: Flack (1983), 2037 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.012 (5)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	Uiso*/Ueq
Br1	0.088547 (13)	0.026408 (2)	0.69853 (3)	0.02305 (5)
O1	0.08828 (10)	0.235769 (16)	0.7073 (2)	0.0206 (2)
N1	0.04426 (12)	0.07710 (2)	1.1084 (2)	0.0181 (3)
N2	0.05839 (12)	0.09353 (2)	0.7759 (2)	0.0168 (3)
N3	0.03392 (13)	0.11442 (2)	1.0691 (2)	0.0175 (3)
N4	0.04759 (10)	0.133332 (18)	0.9574 (2)	0.0156 (2)
C1	0.05708 (15)	0.05747 (3)	1.0215 (3)	0.0194 (3)
C2	0.07009 (14)	0.05472 (3)	0.8133 (3)	0.0182 (3)
C3	0.06893 (12)	0.07344 (2)	0.6943 (3)	0.0176 (3)
C4	0.04600 (12)	0.09446 (2)	0.9789 (2)	0.0149 (3)
C5	0.03372 (14)	0.15154 (3)	1.0534 (3)	0.0165 (3)
C6	0.04819 (11)	0.17289 (2)	0.9545 (3)	0.0147 (3)
C7	0.03424 (14)	0.19218 (3)	1.0688 (2)	0.0183 (3)
C8	0.04797 (14)	0.21285 (2)	0.9828 (2)	0.0186 (3)
C9	0.07649 (14)	0.21461 (3)	0.7790 (2)	0.0167 (3)
C10	0.09188 (14)	0.19569 (3)	0.6627 (2)	0.0167 (3)
C11	0.07730 (14)	0.17500 (3)	0.7492 (2)	0.0167 (3)
C12	0.11941 (17)	0.23826 (3)	0.5009 (3)	0.0242 (4)
O1W	0.24687 (11)	0.12558 (2)	0.72556 (19)	0.0203 (3)
H1W1	0.184 (2)	0.1255 (4)	0.749 (4)	0.037 (7)*
H2W1	0.2655 (18)	0.1332 (4)	0.826 (4)	0.027 (6)*
H1N3	0.0212 (17)	0.1149 (3)	1.189 (5)	0.030 (6)*
H1A	0.0590 (17)	0.0449 (4)	1.110 (3)	0.023 (5)*
H3A	0.0769 (19)	0.0728 (4)	0.546 (4)	0.035 (7)*
H5A	0.0120 (15)	0.1507 (3)	1.198 (4)	0.022 (5)*
H7A	0.0149 (15)	0.1910 (3)	1.218 (4)	0.020 (5)*
H8A	0.041 (2)	0.2255 (4)	1.052 (4)	0.036 (7)*
H10A	0.1133 (19)	0.1960 (4)	0.522 (4)	0.036 (6)*
H11A	0.0919 (16)	0.1621 (3)	0.667 (4)	0.023 (5)*
H12A	0.1909 (19)	0.2312 (3)	0.491 (4)	0.033 (6)*
H12B	0.1262 (15)	0.2538 (3)	0.476 (4)	0.023 (5)*
H12C	0.0727 (17)	0.2324 (4)	0.415 (4)	0.031 (6)*

	U11	U22	U33	U12	U13	U23
Br1	0.02252 (8)	0.01183 (6)	0.03480 (9)	0.00168 (6)	−0.00211 (8)	−0.00497 (7)
O1	0.0280 (6)	0.0115 (4)	0.0223 (5)	−0.0010 (5)	−0.0027 (5)	0.0006 (6)
N1	0.0205 (8)	0.0142 (6)	0.0195 (7)	0.0001 (5)	0.0023 (6)	0.0035 (5)
N2	0.0206 (7)	0.0128 (6)	0.0171 (6)	0.0004 (5)	0.0013 (5)	−0.0002 (5)
N3	0.0270 (8)	0.0122 (6)	0.0133 (6)	0.0003 (6)	0.0036 (6)	0.0007 (5)
N4	0.0195 (6)	0.0118 (5)	0.0156 (6)	−0.0014 (5)	0.0001 (6)	0.0011 (5)
C1	0.0193 (9)	0.0127 (7)	0.0261 (8)	−0.0008 (6)	0.0026 (7)	0.0035 (6)
C2	0.0152 (8)	0.0123 (7)	0.0273 (9)	−0.0005 (6)	0.0001 (6)	−0.0020 (6)
C3	0.0165 (8)	0.0152 (6)	0.0211 (7)	0.0015 (5)	0.0001 (8)	−0.0020 (7)
C4	0.0149 (7)	0.0123 (6)	0.0176 (8)	−0.0002 (5)	0.0011 (6)	0.0006 (5)
C5	0.0194 (9)	0.0138 (7)	0.0164 (7)	0.0013 (6)	0.0009 (6)	−0.0002 (5)
C6	0.0147 (7)	0.0125 (6)	0.0168 (6)	0.0011 (5)	−0.0007 (7)	−0.0007 (6)
C7	0.0226 (9)	0.0159 (7)	0.0164 (7)	0.0017 (6)	−0.0009 (6)	−0.0017 (6)
C8	0.0236 (8)	0.0127 (7)	0.0195 (8)	0.0020 (6)	−0.0029 (7)	−0.0040 (6)
C9	0.0180 (8)	0.0106 (7)	0.0216 (7)	−0.0002 (6)	−0.0041 (6)	0.0006 (5)
C10	0.0195 (8)	0.0152 (6)	0.0154 (8)	−0.0006 (6)	0.0004 (6)	−0.0011 (5)
C11	0.0210 (9)	0.0127 (6)	0.0164 (8)	0.0019 (6)	−0.0006 (6)	−0.0021 (5)
C12	0.0258 (10)	0.0161 (7)	0.0307 (10)	−0.0008 (7)	0.0068 (8)	0.0045 (6)
O1W	0.0256 (7)	0.0202 (5)	0.0152 (6)	−0.0051 (5)	0.0025 (6)	−0.0026 (5)

Br1—C2	1.8886 (17)	C5—H5A	0.99 (2)
O1—C9	1.3745 (19)	C6—C7	1.401 (2)
O1—C12	1.422 (2)	C6—C11	1.406 (2)
N1—C1	1.329 (2)	C7—C8	1.386 (2)
N1—C4	1.352 (2)	C7—H7A	1.01 (2)
N2—C3	1.337 (2)	C8—C9	1.392 (2)
N2—C4	1.343 (2)	C8—H8A	0.89 (2)
N3—C4	1.356 (2)	C9—C10	1.392 (2)
N3—N4	1.3719 (18)	C10—C11	1.389 (2)
N3—H1N3	0.81 (3)	C10—H10A	0.96 (2)
N4—C5	1.284 (2)	C11—H11A	0.97 (2)
C1—C2	1.387 (3)	C12—H12A	1.03 (2)
C1—H1A	0.95 (2)	C12—H12B	0.957 (19)
C2—C3	1.377 (2)	C12—H12C	0.90 (3)
C3—H3A	0.98 (3)	O1W—H1W1	0.83 (3)
C5—C6	1.459 (2)	O1W—H2W1	0.84 (3)
C9—O1—C12	117.21 (13)	C11—C6—C5	122.81 (14)
C1—N1—C4	115.10 (14)	C8—C7—C6	121.30 (15)
C3—N2—C4	116.63 (14)	C8—C7—H7A	119.3 (9)
C4—N3—N4	119.77 (14)	C6—C7—H7A	119.4 (9)
C4—N3—H1N3	118.9 (14)	C7—C8—C9	119.66 (14)
N4—N3—H1N3	121.3 (14)	C7—C8—H8A	123.6 (17)
C5—N4—N3	115.91 (15)	C9—C8—H8A	116.8 (17)
N1—C1—C2	123.06 (16)	O1—C9—C10	124.35 (15)
N1—C1—H1A	117.1 (13)	O1—C9—C8	115.47 (14)
C2—C1—H1A	119.8 (13)	C10—C9—C8	120.17 (14)
C3—C2—C1	117.26 (16)	C11—C10—C9	119.95 (14)
C3—C2—Br1	121.57 (14)	C11—C10—H10A	116.7 (14)
C1—C2—Br1	121.17 (14)	C9—C10—H10A	123.3 (14)
N2—C3—C2	121.59 (19)	C10—C11—C6	120.72 (14)
N2—C3—H3A	116.5 (15)	C10—C11—H11A	118.3 (13)
C2—C3—H3A	121.9 (15)	C6—C11—H11A	120.9 (13)
N2—C4—N1	126.34 (14)	O1—C12—H12A	105.9 (13)
N2—C4—N3	118.98 (13)	O1—C12—H12B	106.9 (14)
N1—C4—N3	114.68 (14)	H12A—C12—H12B	108.1 (17)
N4—C5—C6	121.68 (15)	O1—C12—H12C	111.1 (15)
N4—C5—H5A	117.8 (10)	H12A—C12—H12C	114 (2)
C6—C5—H5A	120.5 (10)	H12B—C12—H12C	110 (2)
C7—C6—C11	118.19 (14)	H1W1—O1W—H2W1	98 (2)
C7—C6—C5	118.99 (16)
C4—N3—N4—C5	179.31 (15)	N4—C5—C6—C7	−178.50 (16)
C4—N1—C1—C2	−0.8 (3)	N4—C5—C6—C11	0.4 (3)
N1—C1—C2—C3	−0.3 (3)	C11—C6—C7—C8	0.4 (3)
N1—C1—C2—Br1	179.74 (14)	C5—C6—C7—C8	179.38 (16)
C4—N2—C3—C2	−1.9 (2)	C6—C7—C8—C9	−0.2 (3)
C1—C2—C3—N2	1.7 (3)	C12—O1—C9—C10	−0.7 (2)
Br1—C2—C3—N2	−178.33 (12)	C12—O1—C9—C8	178.75 (17)
C3—N2—C4—N1	0.8 (3)	C7—C8—C9—O1	180.00 (15)
C3—N2—C4—N3	−179.34 (15)	C7—C8—C9—C10	−0.5 (3)
C1—N1—C4—N2	0.6 (3)	O1—C9—C10—C11	−179.58 (15)
C1—N1—C4—N3	−179.35 (16)	C8—C9—C10—C11	0.9 (3)
N4—N3—C4—N2	−8.4 (2)	C9—C10—C11—C6	−0.7 (3)
N4—N3—C4—N1	171.56 (15)	C7—C6—C11—C10	0.1 (2)
N3—N4—C5—C6	178.45 (14)	C5—C6—C11—C10	−178.87 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···N2	0.84 (3)	2.55 (3)	3.153 (2)	131 (2)
O1W—H1W1···N4	0.84 (3)	2.30 (3)	3.0511 (19)	151 (2)
O1W—H2W1···N2i	0.84 (3)	2.01 (3)	2.8341 (19)	169 (2)
N3—H1N3···O1Wii	0.81 (3)	1.99 (3)	2.7773 (19)	165.1 (19)
C5—H5A···O1Wii	0.99 (2)	2.43 (2)	3.257 (2)	140.7 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯N2	0.84 (3)	2.55 (3)	3.153 (2)	131 (2)
O1W—H1W1⋯N4	0.84 (3)	2.30 (3)	3.0511 (19)	151 (2)
O1W—H2W1⋯N2i	0.84 (3)	2.01 (3)	2.8341 (19)	169 (2)
N3—H1N3⋯O1Wii	0.81 (3)	1.99 (3)	2.7773 (19)	165.1 (19)
C5—H5A⋯O1Wii	0.99 (2)	2.43 (2)	3.257 (2)	140.7 (13)

Symmetry codes: (i) ; (ii) .