N-(1,10-Phenanthrolin-5-yl)-4-(2-pyridyl)-benzamide monohydrate.

In the title mol-ecule, C(24)H(16)N(4)O·H(2)O, the benzene ring of the 1,10-phenanthroline group and that of the 2-phenyl-pyridine group are respectively twisted by 67.9 (1) and 15.3 (3)° from the carbamoyl group defined by the plane of the O=C-N group of atoms. The water mol-ecule is hydrogen bonded to one of the phenanthroline N atoms. In the crystal structure, significant π-π stacking inter-actions occur, with centroid-to-centroid separations in the range 3.567-3.681 (2) Å.

Related literature

For background information, see: Ozawa & Sakai (2007 ▶); Ozawa et al. (2006 ▶, 2007 ▶); Sakai & Ozawa (2007 ▶).

Experimental

Crystal data

C24H16N4O·H2O

M = 394.42

Triclinic,

a = 8.226 (2) Å

b = 9.357 (3) Å

c = 13.849 (4) Å

α = 73.638 (3)°

β = 82.883 (4)°

γ = 64.695 (3)°

V = 924.7 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 (2) K

0.13 × 0.05 × 0.05 mm

Data collection

Bruker SMART APEX CCD-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.992, T max = 0.995

8821 measured reflections

3222 independent reflections

2284 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.114

S = 1.03

3222 reflections

279 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: KENX (Sakai, 2004 ▶); software used to prepare material for publication: SHELXL97, TEXSAN (Molecular Structure Corporation, 2001 ▶), KENX and ORTEPII (Johnson, 1976 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029851/lh2685sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029851/lh2685Isup2.hkl

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

C24H16N4O·H2O	Z = 2
Mr = 394.42	F(000) = 412
Triclinic, P1	? # Insert any comments here.
Hall symbol: -P 1	Dx = 1.417 Mg m−3
a = 8.226 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.357 (3) Å	Cell parameters from 7706 reflections
c = 13.849 (4) Å	θ = 2.5–25.0°
α = 73.638 (3)°	µ = 0.09 mm−1
β = 82.883 (4)°	T = 296 K
γ = 64.695 (3)°	Cube, yellow
V = 924.7 (5) Å3	0.13 × 0.05 × 0.05 mm

Bruker SMART APEX CCD-detector diffractometer	3222 independent reflections
Radiation source: rotating anode with a mirror focusing unit	2284 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.992, Tmax = 0.995	k = −11→11
8821 measured reflections	l = −16→16

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0447P)2 + 0.4023P] where P = (Fo2 + 2Fc2)/3
3222 reflections	(Δ/σ)max < 0.001
279 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. The first 50 frames were rescanned at the end of data collection to evaluate any possible decay phenomenon. Since it was judged to be negligible, no decay correction was applied to the data.

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
O1	0.6321 (2)	0.64738 (18)	0.79108 (12)	0.0325 (4)
O2	0.8041 (2)	0.0010 (2)	0.48055 (13)	0.0320 (4)
N1	0.9204 (2)	0.3157 (2)	0.44978 (14)	0.0227 (4)
N2	0.7555 (2)	0.2000 (2)	0.61822 (14)	0.0240 (4)
N3	0.4357 (2)	0.7537 (2)	0.66380 (13)	0.0234 (4)
H3	0.3311	0.8231	0.6404	0.028*
N4	0.1196 (2)	1.2126 (2)	1.05472 (14)	0.0283 (5)
C1	0.9942 (3)	0.3743 (3)	0.36656 (17)	0.0261 (5)
H1	1.0806	0.3002	0.3340	0.031*
C2	0.9506 (3)	0.5398 (3)	0.32478 (17)	0.0269 (5)
H2	1.0048	0.5749	0.2654	0.032*
C3	0.8266 (3)	0.6497 (3)	0.37276 (17)	0.0242 (5)
H3A	0.7957	0.7610	0.3466	0.029*
C4	0.7459 (3)	0.5937 (2)	0.46189 (16)	0.0202 (5)
C5	0.7961 (3)	0.4238 (2)	0.49721 (16)	0.0194 (5)
C6	0.7149 (3)	0.3620 (2)	0.58924 (16)	0.0196 (5)
C7	0.5959 (3)	0.4720 (2)	0.64404 (16)	0.0203 (5)
C8	0.5206 (3)	0.4072 (3)	0.73217 (17)	0.0251 (5)
H8	0.4421	0.4754	0.7708	0.030*
C9	0.5626 (3)	0.2438 (3)	0.76114 (18)	0.0281 (5)
H9	0.5137	0.1991	0.8197	0.034*
C10	0.6796 (3)	0.1450 (3)	0.70180 (18)	0.0274 (5)
H10	0.7061	0.0338	0.7219	0.033*
C11	0.6237 (3)	0.7014 (2)	0.51907 (17)	0.0222 (5)
H11	0.5914	0.8133	0.4952	0.027*
C12	0.5542 (3)	0.6440 (2)	0.60716 (16)	0.0207 (5)
C13	0.4863 (3)	0.7494 (3)	0.75393 (17)	0.0235 (5)
C14	0.3587 (3)	0.8709 (2)	0.80803 (16)	0.0214 (5)
C15	0.1777 (3)	0.9621 (2)	0.78548 (17)	0.0226 (5)
H15	0.1289	0.9500	0.7328	0.027*
C16	0.0692 (3)	1.0709 (3)	0.84065 (17)	0.0241 (5)
H16	−0.0519	1.1309	0.8245	0.029*
C17	0.1378 (3)	1.0925 (2)	0.92009 (16)	0.0214 (5)
C18	0.3183 (3)	0.9973 (3)	0.94320 (18)	0.0273 (5)
H18	0.3666	1.0069	0.9971	0.033*
C19	0.4274 (3)	0.8894 (3)	0.88841 (17)	0.0267 (5)
H19	0.5482	0.8282	0.9052	0.032*
C20	0.0297 (3)	1.2124 (3)	0.97979 (17)	0.0222 (5)
C21	−0.1468 (3)	1.3208 (3)	0.95877 (18)	0.0271 (5)
H21	−0.2065	1.3184	0.9069	0.033*
C22	−0.2342 (3)	1.4330 (3)	1.01517 (18)	0.0303 (6)
H22	−0.3535	1.5064	1.0021	0.036*
C23	−0.1423 (3)	1.4343 (3)	1.09085 (18)	0.0297 (6)
H23	−0.1972	1.5092	1.1297	0.036*
C24	0.0327 (3)	1.3224 (3)	1.10773 (18)	0.0303 (6)
H24	0.0944	1.3232	1.1593	0.036*
H1S	0.809 (4)	0.067 (4)	0.518 (3)	0.093 (12)*
H2S	0.900 (4)	−0.092 (4)	0.494 (2)	0.068 (10)*

	U11	U22	U33	U12	U13	U23
O1	0.0266 (9)	0.0314 (9)	0.0339 (10)	−0.0004 (8)	−0.0089 (8)	−0.0150 (8)
O2	0.0348 (10)	0.0202 (9)	0.0357 (11)	−0.0016 (8)	−0.0115 (8)	−0.0102 (8)
N1	0.0229 (10)	0.0218 (10)	0.0218 (11)	−0.0049 (8)	−0.0011 (8)	−0.0096 (8)
N2	0.0272 (10)	0.0207 (10)	0.0235 (11)	−0.0087 (8)	−0.0050 (9)	−0.0045 (8)
N3	0.0183 (10)	0.0242 (10)	0.0249 (11)	−0.0022 (8)	−0.0025 (8)	−0.0116 (8)
N4	0.0317 (11)	0.0307 (11)	0.0263 (12)	−0.0140 (9)	0.0018 (9)	−0.0120 (9)
C1	0.0248 (13)	0.0314 (13)	0.0209 (14)	−0.0075 (10)	0.0008 (10)	−0.0119 (11)
C2	0.0279 (13)	0.0325 (13)	0.0200 (13)	−0.0125 (11)	−0.0026 (10)	−0.0053 (11)
C3	0.0281 (13)	0.0208 (11)	0.0229 (14)	−0.0099 (10)	−0.0055 (10)	−0.0023 (10)
C4	0.0189 (11)	0.0209 (11)	0.0202 (13)	−0.0064 (9)	−0.0050 (9)	−0.0053 (9)
C5	0.0180 (11)	0.0190 (11)	0.0209 (13)	−0.0050 (9)	−0.0048 (9)	−0.0067 (10)
C6	0.0187 (11)	0.0182 (11)	0.0217 (13)	−0.0063 (9)	−0.0051 (9)	−0.0047 (9)
C7	0.0164 (11)	0.0234 (11)	0.0212 (13)	−0.0064 (9)	−0.0038 (9)	−0.0073 (10)
C8	0.0225 (12)	0.0290 (12)	0.0258 (14)	−0.0102 (10)	0.0024 (10)	−0.0118 (10)
C9	0.0304 (13)	0.0328 (13)	0.0237 (14)	−0.0166 (11)	0.0003 (11)	−0.0055 (11)
C10	0.0322 (13)	0.0213 (11)	0.0286 (15)	−0.0124 (10)	−0.0048 (11)	−0.0020 (11)
C11	0.0218 (12)	0.0152 (11)	0.0265 (14)	−0.0039 (9)	−0.0060 (10)	−0.0044 (10)
C12	0.0177 (11)	0.0211 (11)	0.0222 (13)	−0.0047 (9)	−0.0041 (10)	−0.0075 (10)
C13	0.0222 (12)	0.0225 (12)	0.0250 (14)	−0.0074 (10)	−0.0051 (10)	−0.0055 (10)
C14	0.0232 (12)	0.0179 (11)	0.0233 (13)	−0.0092 (9)	0.0014 (10)	−0.0050 (10)
C15	0.0267 (12)	0.0220 (11)	0.0202 (13)	−0.0104 (10)	−0.0020 (10)	−0.0057 (10)
C16	0.0215 (12)	0.0219 (11)	0.0285 (14)	−0.0074 (10)	−0.0022 (10)	−0.0073 (10)
C17	0.0248 (12)	0.0184 (11)	0.0224 (13)	−0.0109 (10)	0.0004 (10)	−0.0043 (10)
C18	0.0289 (13)	0.0304 (13)	0.0271 (14)	−0.0120 (11)	−0.0042 (11)	−0.0127 (11)
C19	0.0225 (12)	0.0265 (12)	0.0315 (15)	−0.0072 (10)	−0.0026 (10)	−0.0117 (11)
C20	0.0262 (12)	0.0219 (11)	0.0224 (13)	−0.0150 (10)	0.0027 (10)	−0.0046 (10)
C21	0.0278 (13)	0.0270 (12)	0.0281 (14)	−0.0121 (10)	−0.0003 (11)	−0.0081 (11)
C22	0.0257 (13)	0.0285 (13)	0.0364 (15)	−0.0103 (10)	0.0059 (11)	−0.0116 (11)
C23	0.0321 (14)	0.0325 (13)	0.0310 (15)	−0.0168 (11)	0.0106 (11)	−0.0166 (11)
C24	0.0373 (15)	0.0349 (14)	0.0257 (14)	−0.0188 (12)	0.0028 (11)	−0.0133 (11)

O1—C13	1.229 (2)	C9—C10	1.388 (3)
O2—H1S	0.92 (4)	C9—H9	0.9300
O2—H2S	0.88 (3)	C10—H10	0.9300
N1—C1	1.324 (3)	C11—C12	1.351 (3)
N1—C5	1.351 (3)	C11—H11	0.9300
N2—C10	1.325 (3)	C13—C14	1.490 (3)
N2—C6	1.352 (3)	C14—C15	1.386 (3)
N3—C13	1.349 (3)	C14—C19	1.392 (3)
N3—C12	1.424 (3)	C15—C16	1.381 (3)
N3—H3	0.8600	C15—H15	0.9300
N4—C24	1.331 (3)	C16—C17	1.395 (3)
N4—C20	1.347 (3)	C16—H16	0.9300
C1—C2	1.391 (3)	C17—C18	1.388 (3)
C1—H1	0.9300	C17—C20	1.490 (3)
C2—C3	1.363 (3)	C18—C19	1.375 (3)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.403 (3)	C19—H19	0.9300
C3—H3A	0.9300	C20—C21	1.378 (3)
C4—C5	1.410 (3)	C21—C22	1.381 (3)
C4—C11	1.428 (3)	C21—H21	0.9300
C5—C6	1.452 (3)	C22—C23	1.372 (3)
C6—C7	1.410 (3)	C22—H22	0.9300
C7—C8	1.400 (3)	C23—C24	1.371 (3)
C7—C12	1.441 (3)	C23—H23	0.9300
C8—C9	1.362 (3)	C24—H24	0.9300
C8—H8	0.9300
H1S—O2—H2S	109 (3)	C11—C12—N3	120.22 (19)
C1—N1—C5	117.71 (19)	C11—C12—C7	120.60 (19)
C10—N2—C6	117.68 (19)	N3—C12—C7	119.2 (2)
C13—N3—C12	120.42 (17)	O1—C13—N3	121.2 (2)
C13—N3—H3	119.8	O1—C13—C14	120.86 (19)
C12—N3—H3	119.8	N3—C13—C14	117.90 (18)
C24—N4—C20	117.8 (2)	C15—C14—C19	118.5 (2)
N1—C1—C2	124.1 (2)	C15—C14—C13	124.69 (19)
N1—C1—H1	118.0	C19—C14—C13	116.80 (19)
C2—C1—H1	118.0	C16—C15—C14	120.5 (2)
C3—C2—C1	118.5 (2)	C16—C15—H15	119.7
C3—C2—H2	120.7	C14—C15—H15	119.7
C1—C2—H2	120.7	C15—C16—C17	121.3 (2)
C2—C3—C4	119.6 (2)	C15—C16—H16	119.3
C2—C3—H3A	120.2	C17—C16—H16	119.3
C4—C3—H3A	120.2	C18—C17—C16	117.4 (2)
C3—C4—C5	117.66 (19)	C18—C17—C20	118.70 (19)
C3—C4—C11	122.32 (19)	C16—C17—C20	123.92 (19)
C5—C4—C11	119.9 (2)	C19—C18—C17	121.7 (2)
N1—C5—C4	122.4 (2)	C19—C18—H18	119.2
N1—C5—C6	118.61 (18)	C17—C18—H18	119.2
C4—C5—C6	119.02 (19)	C18—C19—C14	120.5 (2)
N2—C6—C7	122.6 (2)	C18—C19—H19	119.7
N2—C6—C5	118.13 (19)	C14—C19—H19	119.7
C7—C6—C5	119.30 (19)	N4—C20—C21	121.5 (2)
C8—C7—C6	117.37 (19)	N4—C20—C17	114.92 (19)
C8—C7—C12	122.94 (19)	C21—C20—C17	123.5 (2)
C6—C7—C12	119.7 (2)	C20—C21—C22	119.6 (2)
C9—C8—C7	119.7 (2)	C20—C21—H21	120.2
C9—C8—H8	120.1	C22—C21—H21	120.2
C7—C8—H8	120.1	C23—C22—C21	118.9 (2)
C8—C9—C10	118.9 (2)	C23—C22—H22	120.6
C8—C9—H9	120.6	C21—C22—H22	120.6
C10—C9—H9	120.6	C24—C23—C22	118.2 (2)
N2—C10—C9	123.8 (2)	C24—C23—H23	120.9
N2—C10—H10	118.1	C22—C23—H23	120.9
C9—C10—H10	118.1	N4—C24—C23	124.0 (2)
C12—C11—C4	121.33 (19)	N4—C24—H24	118.0
C12—C11—H11	119.3	C23—C24—H24	118.0
C4—C11—H11	119.3
C5—N1—C1—C2	−0.5 (3)	C8—C7—C12—C11	−176.69 (19)
N1—C1—C2—C3	1.2 (3)	C6—C7—C12—C11	2.1 (3)
C1—C2—C3—C4	−0.4 (3)	C8—C7—C12—N3	2.0 (3)
C2—C3—C4—C5	−0.9 (3)	C6—C7—C12—N3	−179.23 (17)
C2—C3—C4—C11	175.97 (19)	C12—N3—C13—O1	−2.9 (3)
C1—N1—C5—C4	−0.9 (3)	C12—N3—C13—C14	178.02 (19)
C1—N1—C5—C6	−179.31 (17)	O1—C13—C14—C15	−163.3 (2)
C3—C4—C5—N1	1.6 (3)	N3—C13—C14—C15	15.8 (3)
C11—C4—C5—N1	−175.33 (18)	O1—C13—C14—C19	15.0 (3)
C3—C4—C5—C6	−179.97 (17)	N3—C13—C14—C19	−165.89 (19)
C11—C4—C5—C6	3.1 (3)	C19—C14—C15—C16	1.1 (3)
C10—N2—C6—C7	−0.3 (3)	C13—C14—C15—C16	179.4 (2)
C10—N2—C6—C5	−179.43 (18)	C14—C15—C16—C17	0.1 (3)
N1—C5—C6—N2	−6.0 (3)	C15—C16—C17—C18	−1.6 (3)
C4—C5—C6—N2	175.59 (17)	C15—C16—C17—C20	177.5 (2)
N1—C5—C6—C7	174.89 (18)	C16—C17—C18—C19	2.0 (3)
C4—C5—C6—C7	−3.6 (3)	C20—C17—C18—C19	−177.2 (2)
N2—C6—C7—C8	0.8 (3)	C17—C18—C19—C14	−0.8 (4)
C5—C6—C7—C8	179.88 (17)	C15—C14—C19—C18	−0.8 (3)
N2—C6—C7—C12	−178.05 (18)	C13—C14—C19—C18	−179.2 (2)
C5—C6—C7—C12	1.1 (3)	C24—N4—C20—C21	−0.6 (3)
C6—C7—C8—C9	−0.5 (3)	C24—N4—C20—C17	176.9 (2)
C12—C7—C8—C9	178.31 (19)	C18—C17—C20—N4	−2.1 (3)
C7—C8—C9—C10	−0.2 (3)	C16—C17—C20—N4	178.8 (2)
C6—N2—C10—C9	−0.5 (3)	C18—C17—C20—C21	175.3 (2)
C8—C9—C10—N2	0.8 (3)	C16—C17—C20—C21	−3.8 (3)
C3—C4—C11—C12	−176.79 (19)	N4—C20—C21—C22	0.3 (3)
C5—C4—C11—C12	0.0 (3)	C17—C20—C21—C22	−177.0 (2)
C4—C11—C12—N3	178.66 (18)	C20—C21—C22—C23	0.4 (3)
C4—C11—C12—C7	−2.6 (3)	C21—C22—C23—C24	−0.7 (3)
C13—N3—C12—C11	−112.9 (2)	C20—N4—C24—C23	0.3 (3)
C13—N3—C12—C7	68.4 (3)	C22—C23—C24—N4	0.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1S···N2	0.92 (4)	2.01 (4)	2.905 (2)	163 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1S⋯N2	0.92 (4)	2.01 (4)	2.905 (2)	163 (3)