(S)-1-(1-Ferrocenylmethyl-1H-benz-imidazol-2-yl)ethanol monohydrate.

In the structure of the title compound, [Fe(C(5)H(5))(C(15)H(15)N(2)O)]·H(2)O, the unsubstituted cyclo-penta-diene (Cp) ring is disordered over two positions, with site-occupancy factors of 0.636 (12) and 0.364 (12). The dihedral angles between the planes of the substituted Cp ring and the major and minor components of the disordered ring are 0.8 (3) and 3.4 (6)°, respectively. The crystal packing is stabilized by inter-molecular O-H⋯O hydrogen bonds, forming zigzag chains running parallel to the a axis.

Related literature

For applications of ferrocene compounds, see: Savage et al. (2006 ▶); Carr et al. (2001 ▶). For the biological and pharmaceutical activity of imidazole and benzimidazole derivatives, see: Matsuno et al. (2000 ▶); Garuti et al. (1999 ▶). For the synthesis and crystal structure of (±)-1-(1H-benzimidazol-2-yl)ethanol, see: Xia & Xu (2008 ▶).

Experimental

Crystal data

[Fe(C5H5)(C15H15N2O)]·H2O

M = 378.25

Orthorhombic,

a = 7.678 (5) Å

b = 12.480 (8) Å

c = 19.428 (12) Å

V = 1862 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.83 mm−1

T = 293 K

0.40 × 0.35 × 0.30 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.724, T max = 0.785

19049 measured reflections

4236 independent reflections

3622 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.113

S = 1.05

4236 reflections

243 parameters

146 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 1811 Friedel pairs

Flack parameter: 0.03 (2)

Data collection: CrystalClear (Rigaku, 2005 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809023575/rz2334sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023575/rz2334Isup2.hkl

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

[Fe(C5H5)(C15H15N2O)]·H2O	F(000) = 792
Mr = 378.25	Dx = 1.349 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4425 reflections
a = 7.678 (5) Å	θ = 2.7–27.5°
b = 12.480 (8) Å	µ = 0.83 mm−1
c = 19.428 (12) Å	T = 293 K
V = 1862 (2) Å3	Block, colourless
Z = 4	0.40 × 0.35 × 0.30 mm

Rigaku SCXmini diffractometer	4236 independent reflections
Radiation source: fine-focus sealed tube	3622 reflections with I > 2σ(I)
graphite	Rint = 0.042
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 2.7°
ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −16→16
Tmin = 0.724, Tmax = 0.785	l = −25→25
19049 measured reflections

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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0566P)2 + 0.1498P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
4236 reflections	Δρmax = 0.32 e Å−3
243 parameters	Δρmin = −0.21 e Å−3
146 restraints	Absolute structure: Flack (1983), 1811 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (2)

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	Occ. (<1)
Fe1	0.12377 (5)	0.11965 (3)	0.10136 (2)	0.05548 (14)
C1	0.2965 (13)	0.2388 (10)	0.0874 (6)	0.076 (2)	0.636 (12)
H1	0.3040	0.3018	0.1128	0.092*	0.636 (12)
C2	0.3868 (13)	0.1411 (10)	0.1064 (6)	0.088 (2)	0.636 (12)
H2	0.4582	0.1309	0.1445	0.105*	0.636 (12)
C3	0.3440 (15)	0.0626 (9)	0.0545 (6)	0.090 (2)	0.636 (12)
H3	0.3799	−0.0085	0.0519	0.108*	0.636 (12)
C4	0.2340 (16)	0.1193 (11)	0.0081 (5)	0.087 (2)	0.636 (12)
H4	0.1888	0.0883	−0.0316	0.104*	0.636 (12)
C5	0.198 (2)	0.2298 (13)	0.0278 (7)	0.081 (2)	0.636 (12)
H5	0.1278	0.2805	0.0063	0.097*	0.636 (12)
C1'	0.344 (2)	0.218 (2)	0.0982 (13)	0.076 (2)	0.364 (12)
H1'	0.3815	0.2628	0.1333	0.092*	0.364 (12)
C2'	0.384 (3)	0.104 (2)	0.0815 (11)	0.088 (2)	0.364 (12)
H2'	0.4599	0.0594	0.1059	0.105*	0.364 (12)
C3'	0.294 (3)	0.0763 (17)	0.0258 (12)	0.090 (2)	0.364 (12)
H3'	0.3024	0.0082	0.0068	0.108*	0.364 (12)
C4'	0.187 (3)	0.1529 (19)	−0.0023 (11)	0.087 (2)	0.364 (12)
H4'	0.1092	0.1521	−0.0391	0.104*	0.364 (12)
C5'	0.236 (4)	0.233 (2)	0.0447 (15)	0.081 (2)	0.364 (12)
H5'	0.1904	0.3009	0.0384	0.097*	0.364 (12)
C6	0.0499 (5)	0.0507 (3)	0.19164 (17)	0.0656 (8)
H6	0.1226	0.0277	0.2270	0.079*
C7	−0.0067 (6)	−0.0118 (3)	0.1347 (2)	0.0781 (10)
H7	0.0243	−0.0825	0.1260	0.094*
C8	−0.1161 (5)	0.0507 (3)	0.09454 (18)	0.0714 (8)
H8	−0.1717	0.0286	0.0544	0.086*
C9	−0.1290 (4)	0.1537 (3)	0.12467 (16)	0.0617 (7)
H9	−0.1943	0.2108	0.1080	0.074*
C10	−0.0239 (3)	0.1541 (2)	0.18508 (14)	0.0490 (6)
C11	−0.0006 (4)	0.2455 (2)	0.23385 (14)	0.0553 (7)
H11A	0.0989	0.2317	0.2633	0.066*
H11B	0.0226	0.3105	0.2081	0.066*
C12	−0.2966 (4)	0.3248 (2)	0.25873 (14)	0.0531 (7)
C13	−0.3238 (4)	0.3941 (3)	0.20362 (16)	0.0636 (8)
H13A	−0.2437	0.4009	0.1680	0.076*
C14	−0.4778 (5)	0.4525 (3)	0.2051 (2)	0.0791 (11)
H14A	−0.5003	0.5008	0.1698	0.095*
C15	−0.6005 (6)	0.4410 (4)	0.2581 (2)	0.0918 (12)
H15A	−0.7020	0.4818	0.2571	0.110*
C16	−0.5738 (5)	0.3712 (4)	0.3111 (2)	0.0827 (10)
H16A	−0.6565	0.3628	0.3457	0.099*
C17	−0.4184 (4)	0.3126 (3)	0.31211 (16)	0.0632 (8)
C18	−0.1993 (4)	0.2124 (3)	0.33753 (15)	0.0601 (7)
C19	−0.0719 (5)	0.1412 (3)	0.37575 (19)	0.0757 (10)
H19A	−0.0051	0.1004	0.3417	0.091*
C20	−0.1628 (7)	0.0627 (4)	0.4224 (3)	0.1130 (17)
H20A	−0.0778	0.0186	0.4451	0.169*
H20B	−0.2393	0.0183	0.3957	0.169*
H20C	−0.2292	0.1011	0.4563	0.169*
N1	−0.1568 (3)	0.2606 (2)	0.27640 (11)	0.0538 (6)
N2	−0.3554 (4)	0.2401 (2)	0.36061 (13)	0.0683 (7)
O1	0.0467 (4)	0.2076 (3)	0.41300 (18)	0.0971 (9)
H1''	0.1441	0.1808	0.4120	0.146*
OW	0.4102 (5)	0.1890 (3)	0.47061 (15)	0.1251 (12)
HWB	0.4440	0.2535	0.4746	0.188*
HWC	0.3948	0.1621	0.5104	0.188*

	U11	U22	U33	U12	U13	U23
Fe1	0.0499 (2)	0.0611 (2)	0.0554 (2)	0.0041 (2)	0.01120 (19)	0.0056 (2)
C1	0.042 (5)	0.101 (5)	0.086 (5)	−0.012 (3)	0.007 (4)	0.018 (4)
C2	0.051 (2)	0.129 (7)	0.084 (6)	0.007 (4)	0.017 (4)	0.021 (4)
C3	0.072 (6)	0.119 (4)	0.079 (6)	0.029 (3)	0.028 (4)	0.005 (4)
C4	0.079 (7)	0.124 (7)	0.058 (4)	0.009 (4)	0.019 (3)	0.016 (4)
C5	0.068 (7)	0.104 (3)	0.071 (7)	−0.004 (4)	0.012 (3)	0.029 (4)
C1'	0.042 (5)	0.101 (5)	0.086 (5)	−0.012 (3)	0.007 (4)	0.018 (4)
C2'	0.051 (2)	0.129 (7)	0.084 (6)	0.007 (4)	0.017 (4)	0.021 (4)
C3'	0.072 (6)	0.119 (4)	0.079 (6)	0.029 (3)	0.028 (4)	0.005 (4)
C4'	0.079 (7)	0.124 (7)	0.058 (4)	0.009 (4)	0.019 (3)	0.016 (4)
C5'	0.068 (7)	0.104 (3)	0.071 (7)	−0.004 (4)	0.012 (3)	0.029 (4)
C6	0.0729 (19)	0.0610 (17)	0.0627 (18)	0.0124 (15)	0.0137 (16)	0.0162 (15)
C7	0.099 (3)	0.0551 (18)	0.081 (2)	−0.0086 (19)	0.025 (2)	−0.0063 (17)
C8	0.0674 (19)	0.083 (2)	0.0638 (18)	−0.0155 (18)	−0.002 (2)	−0.0108 (17)
C9	0.0454 (14)	0.083 (2)	0.0564 (15)	0.0054 (15)	−0.0020 (13)	−0.0046 (14)
C10	0.0421 (13)	0.0572 (15)	0.0476 (13)	0.0021 (11)	0.0044 (11)	0.0056 (12)
C11	0.0479 (14)	0.0623 (17)	0.0559 (17)	0.0006 (13)	−0.0042 (12)	0.0015 (14)
C12	0.0512 (15)	0.0579 (16)	0.0501 (15)	0.0052 (13)	−0.0090 (12)	−0.0099 (12)
C13	0.0656 (18)	0.0669 (19)	0.0582 (16)	0.0019 (15)	−0.0125 (14)	−0.0036 (15)
C14	0.080 (2)	0.075 (2)	0.082 (2)	0.0162 (19)	−0.033 (2)	−0.0011 (19)
C15	0.077 (3)	0.099 (3)	0.099 (3)	0.031 (2)	−0.018 (2)	−0.020 (2)
C16	0.066 (2)	0.101 (3)	0.081 (2)	0.021 (2)	0.0003 (18)	−0.021 (2)
C17	0.0593 (18)	0.0718 (19)	0.0586 (17)	0.0068 (14)	−0.0012 (14)	−0.0115 (16)
C18	0.071 (2)	0.0627 (18)	0.0471 (14)	0.0018 (15)	−0.0013 (14)	−0.0036 (13)
C19	0.084 (2)	0.077 (2)	0.0655 (18)	0.0096 (18)	−0.0145 (18)	0.0093 (17)
C20	0.129 (4)	0.099 (3)	0.111 (3)	−0.020 (3)	−0.046 (3)	0.045 (3)
N1	0.0567 (14)	0.0597 (13)	0.0449 (11)	0.0061 (11)	−0.0005 (11)	−0.0005 (10)
N2	0.0730 (17)	0.0795 (17)	0.0523 (13)	0.0063 (15)	0.0105 (14)	−0.0061 (12)
O1	0.0643 (15)	0.121 (2)	0.106 (2)	−0.0134 (15)	−0.0203 (16)	0.0323 (18)
OW	0.124 (3)	0.177 (3)	0.0739 (17)	0.012 (3)	0.0232 (18)	0.0031 (19)

Fe1—C5'	1.98 (3)	C7—C8	1.387 (5)
Fe1—C4	2.000 (10)	C7—H7	0.9300
Fe1—C1	2.011 (12)	C8—C9	1.416 (5)
Fe1—C7	2.029 (4)	C8—H8	0.9300
Fe1—C10	2.029 (3)	C9—C10	1.424 (4)
Fe1—C6	2.034 (3)	C9—H9	0.9300
Fe1—C8	2.037 (4)	C10—C11	1.494 (4)
Fe1—C9	2.038 (3)	C11—N1	1.469 (4)
Fe1—C3'	2.036 (17)	C11—H11A	0.9700
Fe1—C2	2.040 (10)	C11—H11B	0.9700
Fe1—C2'	2.05 (2)	C12—N1	1.383 (4)
Fe1—C3	2.048 (8)	C12—C13	1.392 (4)
C1—C5	1.388 (12)	C12—C17	1.404 (4)
C1—C2	1.451 (13)	C13—C14	1.390 (5)
C1—H1	0.9300	C13—H13A	0.9300
C2—C3	1.444 (14)	C14—C15	1.403 (6)
C2—H2	0.9300	C14—H14A	0.9300
C3—C4	1.423 (10)	C15—C16	1.365 (6)
C3—H3	0.9300	C15—H15A	0.9300
C4—C5	1.46 (2)	C16—C17	1.400 (5)
C4—H4	0.9300	C16—H16A	0.9300
C5—H5	0.9300	C17—N2	1.393 (4)
C1'—C5'	1.34 (2)	C18—N2	1.325 (4)
C1'—C2'	1.49 (3)	C18—N1	1.370 (4)
C1'—H1'	0.9300	C18—C19	1.516 (5)
C2'—C3'	1.33 (2)	C19—O1	1.428 (5)
C2'—H2'	0.9300	C19—C20	1.507 (6)
C3'—C4'	1.37 (2)	C19—H19A	0.9800
C3'—H3'	0.9300	C20—H20A	0.9600
C4'—C5'	1.40 (4)	C20—H20B	0.9600
C4'—H4'	0.9300	C20—H20C	0.9600
C5'—H5'	0.9300	O1—H1''	0.8200
C6—C10	1.415 (4)	OW—HWB	0.8501
C6—C7	1.421 (5)	OW—HWC	0.8500
C6—H6	0.9300
C5'—Fe1—C4	46.8 (9)	Fe1—C1'—H1'	125.5
C5'—Fe1—C1	27.6 (8)	C3'—C2'—C1'	108.2 (18)
C4—Fe1—C1	66.5 (5)	C3'—C2'—Fe1	70.5 (12)
C5'—Fe1—C7	165.0 (8)	C1'—C2'—Fe1	70.4 (12)
C4—Fe1—C7	119.8 (4)	C3'—C2'—H2'	125.9
C1—Fe1—C7	165.2 (3)	C1'—C2'—H2'	125.9
C5'—Fe1—C10	122.4 (9)	Fe1—C2'—H2'	124.8
C4—Fe1—C10	164.4 (4)	C2'—C3'—C4'	117 (2)
C1—Fe1—C10	108.7 (4)	C2'—C3'—Fe1	71.4 (11)
C7—Fe1—C10	68.85 (13)	C4'—C3'—Fe1	73.6 (13)
C5'—Fe1—C6	154.1 (8)	C2'—C3'—H3'	121.4
C4—Fe1—C6	153.9 (4)	C4'—C3'—H3'	121.4
C1—Fe1—C6	127.8 (4)	Fe1—C3'—H3'	125.2
C7—Fe1—C6	40.95 (14)	C3'—C4'—C5'	94.2 (18)
C10—Fe1—C6	40.76 (12)	C3'—C4'—Fe1	67.7 (12)
C5'—Fe1—C8	131.0 (7)	C5'—C4'—Fe1	65.2 (16)
C4—Fe1—C8	108.8 (4)	C3'—C4'—H4'	132.9
C1—Fe1—C8	154.1 (3)	C5'—C4'—H4'	132.9
C7—Fe1—C8	39.88 (15)	Fe1—C4'—H4'	125.9
C10—Fe1—C8	68.68 (13)	C1'—C5'—C4'	125 (2)
C6—Fe1—C8	68.00 (15)	C1'—C5'—Fe1	75.1 (16)
C5'—Fe1—C9	112.9 (8)	C4'—C5'—Fe1	74.9 (17)
C4—Fe1—C9	127.2 (4)	C1'—C5'—H5'	117.5
C1—Fe1—C9	120.3 (3)	C4'—C5'—H5'	117.5
C7—Fe1—C9	68.11 (16)	Fe1—C5'—H5'	124.1
C10—Fe1—C9	41.00 (11)	C10—C6—C7	107.9 (3)
C6—Fe1—C9	68.35 (13)	C10—C6—Fe1	69.42 (17)
C8—Fe1—C9	40.68 (14)	C7—C6—Fe1	69.3 (2)
C5'—Fe1—C3'	60.7 (11)	C10—C6—H6	126.0
C4—Fe1—C3'	22.4 (5)	C7—C6—H6	126.0
C1—Fe1—C3'	71.2 (7)	Fe1—C6—H6	126.8
C7—Fe1—C3'	109.4 (6)	C8—C7—C6	108.3 (3)
C10—Fe1—C3'	172.7 (8)	C8—C7—Fe1	70.4 (2)
C6—Fe1—C3'	133.4 (7)	C6—C7—Fe1	69.73 (19)
C8—Fe1—C3'	114.8 (6)	C8—C7—H7	125.8
C9—Fe1—C3'	145.6 (7)	C6—C7—H7	125.8
C5'—Fe1—C2	60.2 (7)	Fe1—C7—H7	125.6
C4—Fe1—C2	68.0 (4)	C7—C8—C9	108.7 (3)
C1—Fe1—C2	42.0 (3)	C7—C8—Fe1	69.7 (2)
C7—Fe1—C2	125.4 (3)	C9—C8—Fe1	69.69 (19)
C10—Fe1—C2	119.1 (4)	C7—C8—H8	125.7
C6—Fe1—C2	106.9 (3)	C9—C8—H8	125.7
C8—Fe1—C2	162.5 (4)	Fe1—C8—H8	126.5
C9—Fe1—C2	154.8 (4)	C8—C9—C10	107.7 (3)
C3'—Fe1—C2	55.6 (6)	C8—C9—Fe1	69.6 (2)
C5'—Fe1—C2'	62.6 (10)	C10—C9—Fe1	69.17 (17)
C4—Fe1—C2'	54.3 (6)	C8—C9—H9	126.1
C1—Fe1—C2'	53.3 (7)	C10—C9—H9	126.1
C7—Fe1—C2'	117.7 (7)	Fe1—C9—H9	126.6
C10—Fe1—C2'	135.9 (7)	C6—C10—C9	107.3 (3)
C6—Fe1—C2'	113.2 (6)	C6—C10—C11	126.2 (3)
C8—Fe1—C2'	146.1 (8)	C9—C10—C11	126.4 (3)
C9—Fe1—C2'	173.2 (8)	C6—C10—Fe1	69.82 (17)
C3'—Fe1—C2'	38.1 (7)	C9—C10—Fe1	69.83 (17)
C2—Fe1—C2'	18.9 (6)	C11—C10—Fe1	127.10 (19)
C5'—Fe1—C3	69.0 (9)	N1—C11—C10	110.9 (2)
C4—Fe1—C3	41.1 (3)	N1—C11—H11A	109.5
C1—Fe1—C3	69.7 (5)	C10—C11—H11A	109.5
C7—Fe1—C3	105.6 (3)	N1—C11—H11B	109.5
C10—Fe1—C3	153.1 (4)	C10—C11—H11B	109.5
C6—Fe1—C3	117.8 (4)	H11A—C11—H11B	108.1
C8—Fe1—C3	124.8 (4)	N1—C12—C13	131.8 (3)
C9—Fe1—C3	163.2 (4)	N1—C12—C17	105.7 (3)
C3'—Fe1—C3	19.7 (5)	C13—C12—C17	122.4 (3)
C2—Fe1—C3	41.4 (4)	C14—C13—C12	115.9 (3)
C2'—Fe1—C3	22.5 (5)	C14—C13—H13A	122.0
C5—C1—C2	113.8 (11)	C12—C13—H13A	122.0
C5—C1—Fe1	72.1 (9)	C13—C14—C15	122.2 (4)
C2—C1—Fe1	70.1 (6)	C13—C14—H14A	118.9
C5—C1—H1	123.1	C15—C14—H14A	118.9
C2—C1—H1	123.1	C16—C15—C14	121.2 (4)
Fe1—C1—H1	126.5	C16—C15—H15A	119.4
C3—C2—C1	106.5 (8)	C14—C15—H15A	119.4
C3—C2—Fe1	69.6 (5)	C15—C16—C17	118.2 (4)
C1—C2—Fe1	68.0 (6)	C15—C16—H16A	120.9
C3—C2—H2	126.8	C17—C16—H16A	120.9
C1—C2—H2	126.8	N2—C17—C16	130.1 (3)
Fe1—C2—H2	127.2	N2—C17—C12	109.8 (3)
C4—C3—C2	103.9 (8)	C16—C17—C12	120.1 (3)
C4—C3—Fe1	67.6 (5)	N2—C18—N1	113.2 (3)
C2—C3—Fe1	69.0 (5)	N2—C18—C19	124.8 (3)
C4—C3—H3	128.0	N1—C18—C19	121.9 (3)
C2—C3—H3	128.0	O1—C19—C20	111.6 (3)
Fe1—C3—H3	126.9	O1—C19—C18	108.6 (3)
C3—C4—C5	114.6 (10)	C20—C19—C18	112.2 (4)
C3—C4—Fe1	71.2 (5)	O1—C19—H19A	108.1
C5—C4—Fe1	71.3 (8)	C20—C19—H19A	108.1
C3—C4—H4	122.7	C18—C19—H19A	108.1
C5—C4—H4	122.7	C19—C20—H20A	109.5
Fe1—C4—H4	126.5	C19—C20—H20B	109.5
C1—C5—C4	101.1 (10)	H20A—C20—H20B	109.5
C1—C5—Fe1	68.1 (8)	C19—C20—H20C	109.5
C4—C5—Fe1	66.7 (8)	H20A—C20—H20C	109.5
C1—C5—H5	129.4	H20B—C20—H20C	109.5
C4—C5—H5	129.4	C18—N1—C12	106.5 (2)
Fe1—C5—H5	127.2	C18—N1—C11	128.8 (3)
C5'—C1'—C2'	95 (2)	C12—N1—C11	124.6 (2)
C5'—C1'—Fe1	66.6 (17)	C18—N2—C17	104.7 (3)
C2'—C1'—Fe1	67.4 (12)	C19—O1—H1''	109.5
C5'—C1'—H1'	132.3	HWB—OW—HWC	109.5
C2'—C1'—H1'	132.3

D—H···A	D—H	H···A	D···A	D—H···A
OW—HWB···O1i	0.85	2.37	2.806 (5)	112
O1—H1''···OW	0.82	2.34	3.016 (5)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
OW—HWB⋯O1i	0.85	2.37	2.806 (5)	112
O1—H1′′⋯OW	0.82	2.34	3.016 (5)	140

Symmetry code: (i) .