Bis{2-[(2-benzoyl-hydrazin-1-yl-idene)meth-yl]-6-meth-oxy-phenolato}iron(III) chloride monohydrate.

In the title mononuclear iron(III) complex, [Fe(C(15)H(13)N(2)O(3))(2)]Cl·H(2)O, the Fe(III) atom has a distorted octa-hedral geometry and is six-coordinated by four O atoms and two N atoms from two ligands. In the crystal structure, the complex cations, Cl(-) anions and water mol-ecules are connected into a chain along [100] through N-H⋯O, O-H⋯Cl and N-H⋯Cl hydrogen bonds. Two adjacent chains are linked by O-H⋯O hydrogen bonds.

Related literature

For the applications of metal–Schiff base compounds, see: Dilworth (1976 ▶); Merchant & Clothia (1970 ▶); Pickart et al. (1983 ▶). For the ligand synthesis, see: Pouralimardan et al. (2007 ▶); Sacconi (1954 ▶). For related structures, see: Gao et al. (1998 ▶); Monfared et al. (2007 ▶); Yu et al. (2010 ▶).

Experimental

Crystal data

[Fe(C15H13N2O3)2]Cl·H2O

M = 647.86

Monoclinic,

a = 12.7778 (10) Å

b = 22.7113 (18) Å

c = 10.0604 (7) Å

β = 94.542 (1)°

V = 2910.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.67 mm−1

T = 296 K

0.24 × 0.18 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.857, T max = 0.907

14540 measured reflections

5098 independent reflections

3508 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.153

S = 0.98

5098 reflections

390 parameters

H-atom parameters constrained

Δρmax = 0.95 e Å−3

Δρmin = −0.48 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810023226/hy2322sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023226/hy2322Isup2.hkl

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

[Fe(C15H13N2O3)2]Cl·H2O	F(000) = 1340
Mr = 647.86	Dx = 1.479 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4767 reflections
a = 12.7778 (10) Å	θ = 4.8–51.7°
b = 22.7113 (18) Å	µ = 0.67 mm−1
c = 10.0604 (7) Å	T = 296 K
β = 94.542 (1)°	Block, black
V = 2910.4 (4) Å3	0.24 × 0.18 × 0.15 mm
Z = 4

Bruker SMART APEX CCD diffractometer	5098 independent reflections
Radiation source: fine-focus sealed tube	3508 reflections with I > 2σ(I)
graphite	Rint = 0.052
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.857, Tmax = 0.907	k = −27→23
14540 measured reflections	l = −11→10

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0933P)2 + 0.1872P] where P = (Fo2 + 2Fc2)/3
5098 reflections	(Δ/σ)max < 0.001
390 parameters	Δρmax = 0.95 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

	x	y	z	Uiso*/Ueq
Fe1	0.28270 (4)	0.56160 (2)	0.90592 (5)	0.02612 (19)
Cl1	0.87327 (8)	0.66511 (5)	0.74420 (12)	0.0455 (3)
C1	0.0861 (3)	0.69236 (18)	0.5203 (4)	0.0376 (10)
H1A	0.0396	0.7024	0.5832	0.045*
C2	0.0804 (4)	0.7195 (2)	0.3979 (5)	0.0449 (12)
H2A	0.0305	0.7487	0.3787	0.054*
C3	0.1472 (4)	0.7040 (2)	0.3036 (5)	0.0511 (13)
H3A	0.1416	0.7227	0.2211	0.061*
C4	0.2219 (4)	0.6615 (2)	0.3292 (4)	0.0433 (11)
H4A	0.2659	0.6508	0.2640	0.052*
C5	0.2313 (3)	0.63511 (19)	0.4515 (4)	0.0350 (10)
H5A	0.2837	0.6073	0.4703	0.042*
C6	0.1631 (3)	0.64933 (18)	0.5489 (4)	0.0307 (9)
C7	0.1786 (3)	0.61984 (17)	0.6799 (4)	0.0275 (9)
C8	0.0525 (3)	0.58652 (18)	0.9627 (4)	0.0310 (9)
H8A	−0.0129	0.6023	0.9359	0.037*
C9	0.0651 (3)	0.55879 (18)	1.0885 (4)	0.0294 (9)
C10	0.1608 (3)	0.53399 (17)	1.1403 (4)	0.0290 (9)
C11	0.1644 (3)	0.50693 (18)	1.2666 (4)	0.0319 (10)
C12	0.0756 (3)	0.5034 (2)	1.3356 (4)	0.0397 (11)
H12A	0.0786	0.4844	1.4177	0.048*
C13	−0.0175 (3)	0.5278 (2)	1.2842 (4)	0.0440 (12)
H13A	−0.0766	0.5256	1.3322	0.053*
C14	−0.0234 (3)	0.5551 (2)	1.1631 (4)	0.0405 (11)
H14A	−0.0867	0.5716	1.1294	0.049*
C15	0.2726 (4)	0.4590 (2)	1.4393 (4)	0.0500 (13)
H15A	0.3446	0.4478	1.4594	0.075*
H15B	0.2288	0.4246	1.4392	0.075*
H15C	0.2522	0.4862	1.5056	0.075*
C16	0.5865 (3)	0.71820 (18)	1.0512 (4)	0.0353 (10)
H16A	0.6324	0.6914	1.0169	0.042*
C17	0.6243 (4)	0.76907 (19)	1.1109 (4)	0.0400 (11)
H17A	0.6961	0.7766	1.1178	0.048*
C18	0.5563 (4)	0.8090 (2)	1.1605 (4)	0.0435 (12)
H18A	0.5822	0.8436	1.2003	0.052*
C19	0.4499 (4)	0.7979 (2)	1.1514 (4)	0.0444 (12)
H19A	0.4043	0.8250	1.1852	0.053*
C20	0.4108 (3)	0.74682 (18)	1.0923 (4)	0.0356 (10)
H20A	0.3389	0.7395	1.0863	0.043*
C21	0.4784 (3)	0.70675 (17)	1.0423 (4)	0.0294 (9)
C22	0.4344 (3)	0.65140 (17)	0.9850 (4)	0.0257 (9)
C23	0.5028 (3)	0.52154 (17)	0.8316 (4)	0.0257 (9)
H23A	0.5735	0.5297	0.8244	0.031*
C24	0.4618 (3)	0.46776 (17)	0.7770 (4)	0.0267 (9)
C25	0.3558 (3)	0.45109 (17)	0.7842 (4)	0.0269 (9)
C26	0.3226 (3)	0.39603 (18)	0.7277 (4)	0.0303 (9)
C27	0.3928 (3)	0.36044 (19)	0.6688 (4)	0.0351 (10)
H27A	0.3703	0.3246	0.6319	0.042*
C28	0.4968 (3)	0.37752 (19)	0.6638 (4)	0.0366 (10)
H28A	0.5434	0.3527	0.6246	0.044*
C29	0.5312 (3)	0.42949 (18)	0.7147 (4)	0.0327 (10)
H29A	0.6008	0.4404	0.7091	0.039*
C30	0.1794 (4)	0.3313 (2)	0.6782 (6)	0.0551 (14)
H30A	0.1063	0.3280	0.6928	0.083*
H30B	0.2167	0.2981	0.7175	0.083*
H30C	0.1874	0.3321	0.5842	0.083*
N1	0.1015 (3)	0.61943 (14)	0.7608 (3)	0.0307 (8)
H1B	0.0412	0.6352	0.7399	0.037*
N2	0.1262 (2)	0.59143 (14)	0.8822 (3)	0.0260 (7)
N3	0.4973 (2)	0.61077 (13)	0.9384 (3)	0.0277 (8)
H3B	0.5640	0.6158	0.9378	0.033*
N4	0.4475 (2)	0.55953 (13)	0.8906 (3)	0.0231 (7)
O1	0.2638 (2)	0.59602 (12)	0.7150 (3)	0.0307 (6)
O1W	0.7122 (2)	0.60423 (13)	0.9294 (3)	0.0421 (8)
H1WA	0.7368	0.5719	0.9611	0.050*
H1WB	0.7434	0.6240	0.8725	0.050*
O2	0.2468 (2)	0.53545 (13)	1.0763 (3)	0.0346 (7)
O3	0.2611 (2)	0.48627 (13)	1.3112 (3)	0.0396 (7)
O4	0.3375 (2)	0.64162 (12)	0.9791 (3)	0.0318 (7)
O5	0.2873 (2)	0.48311 (12)	0.8409 (3)	0.0323 (7)
O6	0.2204 (2)	0.38391 (13)	0.7375 (3)	0.0423 (8)

	U11	U22	U33	U12	U13	U23
Fe1	0.0196 (3)	0.0345 (3)	0.0245 (3)	0.0041 (2)	0.0039 (2)	0.0024 (3)
Cl1	0.0289 (6)	0.0524 (7)	0.0550 (8)	0.0074 (5)	0.0009 (5)	0.0078 (6)
C1	0.036 (3)	0.040 (3)	0.036 (3)	0.001 (2)	−0.0045 (19)	0.007 (2)
C2	0.045 (3)	0.045 (3)	0.043 (3)	0.001 (2)	−0.008 (2)	0.013 (2)
C3	0.055 (3)	0.062 (3)	0.034 (3)	−0.011 (3)	−0.010 (2)	0.024 (2)
C4	0.046 (3)	0.055 (3)	0.029 (3)	−0.001 (2)	0.001 (2)	0.008 (2)
C5	0.036 (2)	0.042 (3)	0.027 (2)	0.001 (2)	0.0000 (19)	0.002 (2)
C6	0.029 (2)	0.036 (2)	0.027 (2)	−0.0047 (18)	−0.0044 (18)	0.0020 (18)
C7	0.028 (2)	0.028 (2)	0.026 (2)	−0.0035 (17)	0.0018 (17)	−0.0018 (17)
C8	0.026 (2)	0.041 (2)	0.026 (2)	0.0031 (18)	0.0046 (18)	0.0017 (19)
C9	0.024 (2)	0.038 (2)	0.026 (2)	0.0022 (18)	0.0032 (17)	−0.0015 (19)
C10	0.028 (2)	0.032 (2)	0.028 (2)	0.0005 (17)	0.0064 (17)	−0.0040 (18)
C11	0.036 (2)	0.035 (2)	0.025 (2)	−0.0016 (19)	0.0011 (18)	−0.0016 (19)
C12	0.037 (3)	0.056 (3)	0.026 (2)	−0.003 (2)	0.0081 (19)	0.001 (2)
C13	0.034 (3)	0.068 (3)	0.032 (3)	−0.002 (2)	0.013 (2)	0.005 (2)
C14	0.030 (2)	0.058 (3)	0.034 (3)	0.006 (2)	0.0046 (19)	0.007 (2)
C15	0.056 (3)	0.068 (3)	0.026 (2)	0.006 (3)	0.003 (2)	0.017 (2)
C16	0.033 (2)	0.036 (2)	0.037 (3)	0.0015 (19)	0.0023 (19)	−0.001 (2)
C17	0.043 (3)	0.039 (3)	0.036 (3)	−0.005 (2)	−0.005 (2)	0.002 (2)
C18	0.062 (3)	0.039 (3)	0.028 (2)	−0.006 (2)	−0.003 (2)	−0.009 (2)
C19	0.052 (3)	0.041 (3)	0.040 (3)	0.010 (2)	0.003 (2)	−0.009 (2)
C20	0.040 (3)	0.038 (2)	0.029 (2)	0.006 (2)	0.0011 (19)	−0.0023 (19)
C21	0.032 (2)	0.033 (2)	0.022 (2)	−0.0003 (18)	−0.0045 (17)	0.0024 (18)
C22	0.023 (2)	0.033 (2)	0.021 (2)	0.0052 (17)	−0.0003 (16)	0.0050 (17)
C23	0.020 (2)	0.037 (2)	0.020 (2)	0.0047 (17)	0.0027 (16)	0.0028 (17)
C24	0.022 (2)	0.037 (2)	0.020 (2)	0.0021 (17)	−0.0017 (16)	0.0021 (18)
C25	0.028 (2)	0.033 (2)	0.019 (2)	0.0039 (17)	0.0007 (17)	0.0034 (17)
C26	0.027 (2)	0.037 (2)	0.027 (2)	−0.0001 (18)	−0.0022 (17)	0.0054 (18)
C27	0.043 (3)	0.035 (2)	0.027 (2)	0.002 (2)	−0.0001 (19)	−0.0036 (19)
C28	0.033 (2)	0.043 (3)	0.034 (2)	0.008 (2)	0.0037 (19)	−0.010 (2)
C29	0.025 (2)	0.041 (3)	0.032 (2)	0.0027 (18)	0.0034 (18)	−0.0056 (19)
C30	0.041 (3)	0.047 (3)	0.077 (4)	−0.013 (2)	−0.001 (3)	−0.012 (3)
N1	0.0245 (18)	0.040 (2)	0.0274 (19)	0.0083 (15)	0.0023 (14)	0.0098 (15)
N2	0.0231 (17)	0.0344 (19)	0.0201 (17)	0.0038 (14)	−0.0001 (14)	0.0063 (14)
N3	0.0231 (17)	0.0315 (18)	0.0281 (19)	−0.0025 (14)	0.0002 (14)	−0.0003 (15)
N4	0.0208 (16)	0.0286 (17)	0.0197 (16)	0.0011 (14)	−0.0008 (13)	−0.0002 (14)
O1	0.0250 (15)	0.0424 (17)	0.0251 (15)	0.0053 (13)	0.0053 (12)	0.0069 (13)
O1W	0.0332 (17)	0.0456 (19)	0.0476 (19)	0.0050 (14)	0.0044 (14)	0.0046 (15)
O2	0.0249 (15)	0.0553 (19)	0.0242 (15)	0.0088 (13)	0.0043 (12)	0.0116 (13)
O3	0.0346 (17)	0.059 (2)	0.0248 (16)	0.0076 (15)	0.0022 (13)	0.0145 (14)
O4	0.0279 (16)	0.0359 (16)	0.0318 (16)	0.0046 (12)	0.0033 (12)	−0.0048 (13)
O5	0.0235 (15)	0.0342 (16)	0.0399 (17)	0.0001 (12)	0.0073 (12)	−0.0046 (13)
O6	0.0303 (17)	0.0440 (18)	0.053 (2)	−0.0081 (14)	0.0050 (14)	−0.0108 (15)

Fe1—O1	2.070 (3)	C16—C17	1.372 (6)
Fe1—O2	1.904 (3)	C16—C21	1.402 (6)
Fe1—O4	2.062 (3)	C16—H16A	0.9300
Fe1—O5	1.901 (3)	C17—C18	1.377 (6)
Fe1—N2	2.106 (3)	C17—H17A	0.9300
Fe1—N4	2.124 (3)	C18—C19	1.379 (7)
C1—C2	1.373 (6)	C18—H18A	0.9300
C1—C6	1.401 (6)	C19—C20	1.379 (6)
C1—H1A	0.9300	C19—H19A	0.9300
C2—C3	1.372 (7)	C20—C21	1.377 (5)
C2—H2A	0.9300	C20—H20A	0.9300
C3—C4	1.367 (6)	C21—C22	1.476 (5)
C3—H3A	0.9300	C22—O4	1.254 (4)
C4—C5	1.365 (6)	C22—N3	1.334 (5)
C4—H4A	0.9300	C23—N4	1.289 (5)
C5—C6	1.399 (6)	C23—C24	1.422 (5)
C5—H5A	0.9300	C23—H23A	0.9300
C6—C7	1.478 (5)	C24—C25	1.413 (5)
C7—O1	1.241 (5)	C24—C29	1.422 (5)
C7—N1	1.328 (5)	C25—O5	1.303 (4)
C8—N2	1.294 (4)	C25—C26	1.425 (5)
C8—C9	1.411 (5)	C26—O6	1.346 (5)
C8—H8A	0.9300	C26—C27	1.375 (6)
C9—C10	1.408 (5)	C27—C28	1.389 (6)
C9—C14	1.409 (5)	C27—H27A	0.9300
C10—O2	1.317 (4)	C28—C29	1.347 (6)
C10—C11	1.409 (5)	C28—H28A	0.9300
C11—O3	1.364 (5)	C29—H29A	0.9300
C11—C12	1.379 (5)	C30—O6	1.417 (5)
C12—C13	1.375 (6)	C30—H30A	0.9600
C12—H12A	0.9300	C30—H30B	0.9600
C13—C14	1.364 (6)	C30—H30C	0.9600
C13—H13A	0.9300	N1—N2	1.391 (4)
C14—H14A	0.9300	N1—H1B	0.8600
C15—O3	1.428 (5)	N3—N4	1.394 (4)
C15—H15A	0.9600	N3—H3B	0.8600
C15—H15B	0.9600	O1W—H1WA	0.8500
C15—H15C	0.9600	O1W—H1WB	0.8502
O5—Fe1—O2	91.94 (12)	C21—C16—H16A	120.1
O5—Fe1—O4	158.43 (11)	C16—C17—C18	120.2 (4)
O2—Fe1—O4	93.00 (12)	C16—C17—H17A	119.9
O5—Fe1—O1	92.26 (11)	C18—C17—H17A	119.9
O2—Fe1—O1	159.12 (11)	C17—C18—C19	120.2 (4)
O4—Fe1—O1	90.57 (11)	C17—C18—H18A	119.9
O5—Fe1—N2	108.53 (12)	C19—C18—H18A	119.9
O2—Fe1—N2	84.74 (11)	C18—C19—C20	120.3 (4)
O4—Fe1—N2	92.83 (11)	C18—C19—H19A	119.9
O1—Fe1—N2	74.54 (11)	C20—C19—H19A	119.9
O5—Fe1—N4	84.04 (11)	C21—C20—C19	119.8 (4)
O2—Fe1—N4	111.65 (11)	C21—C20—H20A	120.1
O4—Fe1—N4	74.63 (11)	C19—C20—H20A	120.1
O1—Fe1—N4	89.13 (11)	C20—C21—C16	119.9 (4)
N2—Fe1—N4	159.46 (12)	C20—C21—C22	118.4 (4)
C2—C1—C6	118.9 (4)	C16—C21—C22	121.7 (4)
C2—C1—H1A	120.5	O4—C22—N3	118.8 (4)
C6—C1—H1A	120.5	O4—C22—C21	120.9 (3)
C3—C2—C1	120.9 (4)	N3—C22—C21	120.3 (3)
C3—C2—H2A	119.6	N4—C23—C24	123.6 (3)
C1—C2—H2A	119.6	N4—C23—H23A	118.2
C4—C3—C2	121.0 (4)	C24—C23—H23A	118.2
C4—C3—H3A	119.5	C25—C24—C29	119.5 (4)
C2—C3—H3A	119.5	C25—C24—C23	122.4 (3)
C5—C4—C3	119.3 (4)	C29—C24—C23	118.1 (3)
C5—C4—H4A	120.3	O5—C25—C24	123.5 (4)
C3—C4—H4A	120.3	O5—C25—C26	118.4 (3)
C4—C5—C6	120.9 (4)	C24—C25—C26	118.1 (3)
C4—C5—H5A	119.5	O6—C26—C27	125.5 (4)
C6—C5—H5A	119.5	O6—C26—C25	114.2 (3)
C5—C6—C1	118.9 (4)	C27—C26—C25	120.3 (4)
C5—C6—C7	118.2 (4)	C26—C27—C28	120.6 (4)
C1—C6—C7	122.8 (4)	C26—C27—H27A	119.7
O1—C7—N1	120.0 (4)	C28—C27—H27A	119.7
O1—C7—C6	120.3 (3)	C29—C28—C27	121.0 (4)
N1—C7—C6	119.8 (4)	C29—C28—H28A	119.5
N2—C8—C9	124.2 (4)	C27—C28—H28A	119.5
N2—C8—H8A	117.9	C28—C29—C24	120.5 (4)
C9—C8—H8A	117.9	C28—C29—H29A	119.8
C10—C9—C14	119.3 (4)	C24—C29—H29A	119.8
C10—C9—C8	123.0 (3)	O6—C30—H30A	109.5
C14—C9—C8	117.7 (4)	O6—C30—H30B	109.5
O2—C10—C9	122.9 (3)	H30A—C30—H30B	109.5
O2—C10—C11	118.8 (4)	O6—C30—H30C	109.5
C9—C10—C11	118.3 (3)	H30A—C30—H30C	109.5
O3—C11—C12	125.1 (4)	H30B—C30—H30C	109.5
O3—C11—C10	114.3 (3)	C7—N1—N2	114.4 (3)
C12—C11—C10	120.6 (4)	C7—N1—H1B	122.8
C13—C12—C11	120.6 (4)	N2—N1—H1B	122.8
C13—C12—H12A	119.7	C8—N2—N1	117.5 (3)
C11—C12—H12A	119.7	C8—N2—Fe1	129.2 (3)
C14—C13—C12	120.3 (4)	N1—N2—Fe1	113.2 (2)
C14—C13—H13A	119.8	C22—N3—N4	115.3 (3)
C12—C13—H13A	119.8	C22—N3—H3B	122.4
C13—C14—C9	120.8 (4)	N4—N3—H3B	122.4
C13—C14—H14A	119.6	C23—N4—N3	117.7 (3)
C9—C14—H14A	119.6	C23—N4—Fe1	129.1 (3)
O3—C15—H15A	109.5	N3—N4—Fe1	112.6 (2)
O3—C15—H15B	109.5	C7—O1—Fe1	117.7 (2)
H15A—C15—H15B	109.5	H1WA—O1W—H1WB	121.9
O3—C15—H15C	109.5	C10—O2—Fe1	135.8 (3)
H15A—C15—H15C	109.5	C11—O3—C15	118.2 (3)
H15B—C15—H15C	109.5	C22—O4—Fe1	118.6 (2)
C17—C16—C21	119.7 (4)	C25—O5—Fe1	135.6 (2)
C17—C16—H16A	120.1	C26—O6—C30	118.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···Cl1i	0.86	2.25	3.087 (3)	163
N3—H3B···O1W	0.86	1.92	2.759 (4)	164
O1W—H1WA···O5ii	0.85	2.39	3.045 (4)	134
O1W—H1WB···Cl1	0.85	2.37	3.198 (3)	163

Table 1

Selected bond lengths (Å)

Fe1—O1	2.070 (3)
Fe1—O2	1.904 (3)
Fe1—O4	2.062 (3)
Fe1—O5	1.901 (3)
Fe1—N2	2.106 (3)
Fe1—N4	2.124 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯Cl1i	0.86	2.25	3.087 (3)	163
N3—H3B⋯O1W	0.86	1.92	2.759 (4)	164
O1W—H1WA⋯O5ii	0.85	2.39	3.045 (4)	134
O1W—H1WB⋯Cl1	0.85	2.37	3.198 (3)	163

Symmetry codes: (i) ; (ii) .