2-(1H-Imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenol monohydrate

Abstract

The asymmetric unit of the title compound, C₁₉H₁₂N₄O·H₂O, contains one organic molecule and one solvent water mol­ecule, which are connected by N—H⋯O and O—H⋯N hydrogen bonds. In addition, there is one intra­molecular O—H⋯N hydrogen bond. The organic mol­ecule is essentially planar (r.m.s. deviation for all non-H atoms = 0.028 Å).

Related literature

For related literature, see: Yin (2008 ▶). For a related structure, see: Sun et al. (2007 ▶).

Experimental

Crystal data

• C₁₉H₁₂N₄O·H₂O

• M _r = 330.34

• Monoclinic,

• a = 4.5272 (9) Å

• b = 19.822 (4) Å

• c = 16.956 (3) Å

• β = 94.15 (3)°

• V = 1517.6 (5) ų

• Z = 4

• Mo Kα radiation

• μ = 0.10 mm⁻¹

• T = 293 (2) K

• 0.21 × 0.17 × 0.15 mm

Data collection

• Rigaku R-AXIS RAPID diffractometer

• Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.975, T _max = 0.989

• 14107 measured reflections

• 3351 independent reflections

• 1342 reflections with I > 2σ(I)

• R _int = 0.177

Refinement

• R[F ² > 2σ(F ²)] = 0.094

• wR(F ²) = 0.205

• S = 1.02

• 3351 reflections

• 232 parameters

• 3 restraints

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.20 e Å⁻³

• Δρ_min = −0.21 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N3	0.82	1.83	2.569 (5)	149
N4—H4⋯O1W	0.86	1.90	2.744 (4)	169
O1W—HW12⋯N2i	0.863 (18)	1.91 (2)	2.715 (5)	155 (4)
O1W—HW12⋯N1i	0.863 (18)	2.62 (4)	3.255 (5)	131 (3)

Symmetry code: (i) .

supplementary crystallographic information

Comment

1,10-Phenanthroline and its derivatives are commonly used as ligands in metal-organic coordination polymers (Sun et al., 2007; Yin, 2008). The title compound was synthesized from [4,5-f]1,10-phenanthroline. All bond lengths are within normal ranges. The H₂O molecules links the 2-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenol molecules by hydrogen bonds to the nitrogen atoms of the imidazo-phenantholine ring systems.

Experimental

1,10-Phenanthroline-5,6-dione (1.5 mmol) and 2-hydroxybenzaldehyde (1.5 mmol) were dissolved in CH₃COOHCH₃COONH₄ (1:1) solution (30 ml). The mixture was refluxed for 1.5 h under argon, after cooling, this mixture was diluted with water and neutralized with concentrated aqueous ammonia, immediately resulting a yellow precipitate, which was washed with water, acetone and diethyl ether respectively. Crystals of the title compound were obtained by recrystallization from dichloromethane.

Refinement

C- and N-bound H atoms were positioned geometrically (N-H = 0.86 Å and C-H = 0.93-0.96 Å) and refined as riding, with U_iso(H) = 1.2U_eq(carrier). The water H-atoms were located in a difference Fourier map, and were refined with distance restraints of O–H = 0.85±0.01 Å and HW11···HW12 = 1.35±0.01 Å and with U_iso(H) = 1.2U_eq(O).

Figures

Fig. 1.

A perspective view of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C19H12N4O·H2O	F000 = 688
Mr = 330.34	Dx = 1.446 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6908 reflections
a = 4.5272 (9) Å	θ = 3.0–27.5º
b = 19.822 (4) Å	µ = 0.10 mm−1
c = 16.956 (3) Å	T = 293 (2) K
β = 94.15 (3)º	Block, pale yellow
V = 1517.6 (5) Å3	0.21 × 0.17 × 0.15 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	3351 independent reflections
Radiation source: rotating anode	1342 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.177
Detector resolution: 10.0 pixels mm-1	θmax = 27.5º
T = 293(2) K	θmin = 3.2º
ω scans	h = −5→5
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	k = −25→25
Tmin = 0.975, Tmax = 0.989	l = −21→21
14107 measured reflections

Refinement

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)] = 0.094	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.205	w = 1/[σ2(Fo2) + (0.0767P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.006
3351 reflections	Δρmax = 0.20 e Å−3
232 parameters	Δρmin = −0.21 e Å−3
3 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.8402 (11)	0.1329 (2)	1.0945 (2)	0.0583 (13)
H1	0.9502	0.1313	1.1429	0.070*
C2	0.6283 (11)	0.0844 (3)	1.0794 (2)	0.0632 (14)
H2	0.5933	0.0519	1.1172	0.076*
C3	0.4704 (10)	0.0846 (2)	1.0080 (2)	0.0568 (12)
H3	0.3234	0.0526	0.9964	0.068*
C4	0.5324 (9)	0.1337 (2)	0.9525 (2)	0.0454 (11)
C5	0.7451 (9)	0.1833 (2)	0.9742 (2)	0.0436 (10)
C6	0.8102 (9)	0.2370 (2)	0.9201 (2)	0.0434 (10)
C7	1.0598 (11)	0.3337 (2)	0.8980 (3)	0.0622 (13)
H7	1.1926	0.3669	0.9163	0.075*
C8	0.6649 (9)	0.2387 (2)	0.8427 (2)	0.0414 (10)
C9	0.3919 (9)	0.1377 (2)	0.8750 (2)	0.0419 (10)
C10	0.4603 (9)	0.1867 (2)	0.8232 (2)	0.0413 (10)
C11	0.1276 (9)	0.1180 (2)	0.7673 (2)	0.0421 (10)
C12	−0.0845 (9)	0.0871 (2)	0.7108 (2)	0.0467 (11)
C13	−0.2259 (10)	0.0279 (2)	0.7296 (3)	0.0544 (12)
C14	−0.4299 (11)	−0.0019 (3)	0.6760 (3)	0.0685 (14)
H14	−0.5268	−0.0411	0.6895	0.082*
C15	−0.4894 (11)	0.0265 (3)	0.6030 (3)	0.0740 (16)
H15	−0.6268	0.0062	0.5671	0.089*
C16	−0.1476 (10)	0.1140 (2)	0.6352 (2)	0.0610 (13)
H16	−0.0506	0.1529	0.6205	0.073*
C17	−0.3502 (11)	0.0840 (3)	0.5825 (3)	0.0717 (15)
H17	−0.3924	0.1028	0.5327	0.086*
C18	0.9353 (10)	0.3391 (2)	0.8210 (2)	0.0587 (13)
H18	0.9871	0.3745	0.7887	0.070*
C19	0.7362 (10)	0.2917 (2)	0.7935 (2)	0.0486 (11)
H19	0.6485	0.2946	0.7423	0.058*
O1	−0.1730 (7)	−0.00281 (16)	0.80052 (18)	0.0763 (11)
H1A	−0.0499	0.0189	0.8278	0.114*
N1	1.0015 (8)	0.28440 (19)	0.94675 (19)	0.0546 (10)
N2	0.9002 (8)	0.18203 (19)	1.04526 (18)	0.0504 (10)
N3	0.1823 (7)	0.09440 (17)	0.84045 (18)	0.0449 (9)
N4	0.2873 (7)	0.17430 (17)	0.75510 (17)	0.0458 (9)
H4	0.2814	0.1979	0.7125	0.055*
O1W	0.3484 (8)	0.24505 (18)	0.61814 (17)	0.0688 (10)
HW12	0.195 (7)	0.257 (2)	0.588 (2)	0.083*
HW11	0.444 (9)	0.219 (2)	0.590 (2)	0.083*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
C1	0.074 (4)	0.061 (3)	0.039 (2)	0.011 (3)	−0.006 (2)	0.001 (2)
C2	0.075 (4)	0.071 (4)	0.044 (3)	0.008 (3)	0.004 (2)	0.013 (2)
C3	0.064 (3)	0.055 (3)	0.052 (3)	0.001 (3)	0.007 (2)	0.008 (2)
C4	0.049 (3)	0.048 (3)	0.039 (2)	0.007 (2)	0.0045 (19)	0.002 (2)
C5	0.046 (3)	0.044 (3)	0.041 (2)	0.008 (2)	−0.0006 (19)	−0.003 (2)
C6	0.045 (3)	0.039 (3)	0.046 (2)	0.005 (2)	0.002 (2)	−0.005 (2)
C7	0.069 (4)	0.053 (3)	0.063 (3)	−0.012 (3)	−0.009 (2)	−0.009 (3)
C8	0.043 (3)	0.040 (3)	0.041 (2)	0.007 (2)	0.0010 (19)	0.0004 (19)
C9	0.040 (3)	0.039 (3)	0.047 (2)	0.001 (2)	0.0010 (19)	0.000 (2)
C10	0.039 (3)	0.042 (3)	0.041 (2)	0.004 (2)	−0.0061 (19)	−0.001 (2)
C11	0.043 (3)	0.035 (2)	0.047 (2)	0.009 (2)	0.0010 (19)	−0.003 (2)
C12	0.044 (3)	0.042 (3)	0.053 (3)	0.004 (2)	−0.004 (2)	−0.002 (2)
C13	0.055 (3)	0.046 (3)	0.062 (3)	0.006 (2)	0.002 (2)	−0.006 (2)
C14	0.060 (4)	0.056 (3)	0.088 (4)	−0.010 (3)	0.001 (3)	−0.022 (3)
C15	0.066 (4)	0.078 (4)	0.075 (4)	−0.003 (3)	−0.016 (3)	−0.022 (3)
C16	0.058 (3)	0.057 (3)	0.066 (3)	−0.001 (3)	−0.009 (2)	−0.003 (3)
C17	0.072 (4)	0.071 (4)	0.069 (3)	−0.001 (3)	−0.019 (3)	−0.007 (3)
C18	0.069 (4)	0.049 (3)	0.057 (3)	−0.007 (2)	0.001 (2)	0.004 (2)
C19	0.054 (3)	0.046 (3)	0.046 (2)	0.001 (2)	0.000 (2)	0.002 (2)
O1	0.077 (2)	0.066 (2)	0.083 (2)	−0.0178 (19)	−0.0115 (18)	0.0141 (19)
N1	0.063 (3)	0.047 (2)	0.053 (2)	−0.011 (2)	−0.0019 (18)	−0.0013 (19)
N2	0.059 (2)	0.052 (2)	0.0394 (19)	0.0082 (19)	0.0000 (17)	0.0002 (18)
N3	0.043 (2)	0.046 (2)	0.0449 (19)	0.0014 (18)	0.0012 (16)	0.0004 (17)
N4	0.046 (2)	0.044 (2)	0.0463 (19)	0.0008 (18)	−0.0033 (16)	0.0060 (17)
O1W	0.077 (3)	0.071 (3)	0.0559 (19)	0.000 (2)	−0.0092 (16)	0.0158 (17)

Geometric parameters (Å, °)

C1—N2	1.323 (5)	C11—N3	1.332 (5)
C1—C2	1.370 (6)	C11—N4	1.353 (5)
C1—H1	0.9300	C11—C12	1.443 (5)
C2—C3	1.360 (5)	C12—C13	1.384 (6)
C2—H2	0.9300	C12—C16	1.400 (5)
C3—C4	1.397 (5)	C13—O1	1.353 (5)
C3—H3	0.9300	C13—C14	1.380 (6)
C4—C5	1.407 (6)	C14—C15	1.368 (6)
C4—C9	1.420 (5)	C14—H14	0.9300
C5—N2	1.351 (4)	C15—C17	1.360 (7)
C5—C6	1.449 (5)	C15—H15	0.9300
C6—N1	1.334 (5)	C16—C17	1.370 (6)
C6—C8	1.424 (5)	C16—H16	0.9300
C7—N1	1.318 (5)	C17—H17	0.9300
C7—C18	1.389 (5)	C18—C19	1.361 (6)
C7—H7	0.9300	C18—H18	0.9300
C8—C19	1.393 (5)	C19—H19	0.9300
C8—C10	1.410 (5)	O1—H1A	0.8200
C9—C10	1.360 (5)	N4—H4	0.8600
C9—N3	1.378 (5)	O1W—HW12	0.863 (18)
C10—N4	1.370 (4)	O1W—HW11	0.841 (18)
N2—C1—C2	124.9 (4)	C13—C12—C16	117.8 (4)
N2—C1—H1	117.5	C13—C12—C11	120.3 (4)
C2—C1—H1	117.5	C16—C12—C11	121.8 (4)
C3—C2—C1	118.7 (4)	O1—C13—C14	117.4 (4)
C3—C2—H2	120.7	O1—C13—C12	122.0 (4)
C1—C2—H2	120.7	C14—C13—C12	120.6 (4)
C2—C3—C4	118.9 (4)	C15—C14—C13	119.9 (5)
C2—C3—H3	120.5	C15—C14—H14	120.1
C4—C3—H3	120.5	C13—C14—H14	120.1
C3—C4—C5	118.6 (4)	C17—C15—C14	120.8 (5)
C3—C4—C9	124.4 (4)	C17—C15—H15	119.6
C5—C4—C9	117.1 (4)	C14—C15—H15	119.6
N2—C5—C4	121.4 (4)	C17—C16—C12	121.0 (5)
N2—C5—C6	117.6 (4)	C17—C16—H16	119.5
C4—C5—C6	121.0 (3)	C12—C16—H16	119.5
N1—C6—C8	122.8 (4)	C15—C17—C16	119.8 (5)
N1—C6—C5	117.3 (3)	C15—C17—H17	120.1
C8—C6—C5	119.9 (4)	C16—C17—H17	120.1
N1—C7—C18	124.1 (4)	C19—C18—C7	118.8 (4)
N1—C7—H7	117.9	C19—C18—H18	120.6
C18—C7—H7	117.9	C7—C18—H18	120.6
C19—C8—C10	126.0 (3)	C18—C19—C8	119.5 (4)
C19—C8—C6	117.2 (4)	C18—C19—H19	120.3
C10—C8—C6	116.8 (4)	C8—C19—H19	120.3
C10—C9—N3	110.6 (3)	C13—O1—H1A	109.5
C10—C9—C4	122.0 (4)	C7—N1—C6	117.6 (4)
N3—C9—C4	127.4 (4)	C1—N2—C5	117.4 (4)
C9—C10—N4	105.8 (3)	C11—N3—C9	104.6 (3)
C9—C10—C8	123.2 (3)	C11—N4—C10	107.3 (3)
N4—C10—C8	130.9 (4)	C11—N4—H4	126.3
N3—C11—N4	111.5 (3)	C10—N4—H4	126.3
N3—C11—C12	122.5 (4)	HW12—O1W—HW11	105 (3)
N4—C11—C12	125.9 (4)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N3	0.82	1.83	2.569 (5)	149
N4—H4···O1W	0.86	1.90	2.744 (4)	169
O1W—HW12···N2i	0.863 (18)	1.91 (2)	2.715 (5)	155 (4)
O1W—HW12···N1i	0.863 (18)	2.62 (4)	3.255 (5)	131 (3)

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