1,2-Diphenyl-ethane-1,2-diyl diiso-nico-tinate monohydrate.

In the novel title compound, C(26)H(20)N(2)O(4)·H(2)O, the two phenyl rings make a dihedral angle of 45.3 (1)° with each other, and the dihedral angle between the two pyridyl planes is 69.8 (1)°.

Related literature

For general background, see: Aspinall et al. (2003 ▶); Takenaka et al. (2006 ▶); MacMahon et al. (2001 ▶); Schuster et al. (2005 ▶). For related structures, see: Shi et al. (2006 ▶).

Experimental

Crystal data

C26H20N2O4·H2O

M = 442.46

Monoclinic,

a = 11.925 (10) Å

b = 5.826 (5) Å

c = 17.787 (15) Å

β = 105.629 (10)°

V = 1190.1 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 291 (2) K

0.32 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker,2000 ▶) T min = 0.979, T max = 0.981

6535 measured reflections

2566 independent reflections

1816 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.086

S = 1.10

2566 reflections

304 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.11 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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.

Crystal structure: contains datablocks z0612, I. DOI: 10.1107/S1600536808022484/sg2251sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022484/sg2251Isup2.hkl

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

C26H20N2O4·H2O	F(000) = 464
Mr = 442.46	Dx = 1.235 Mg m−3
Monoclinic, P21	Melting point: 327 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 11.925 (10) Å	Cell parameters from 1142 reflections
b = 5.826 (5) Å	θ = 2.4–21.6°
c = 17.787 (15) Å	µ = 0.09 mm−1
β = 105.629 (10)°	T = 291 K
V = 1190.1 (17) Å3	Acicular, colorless
Z = 2	0.32 × 0.24 × 0.22 mm

Bruker SMART APEX CCD diffractometer	2566 independent reflections
Radiation source: sealed tube	1816 reflections with I > 2σ(I)
graphite	Rint = 0.024
phi and ω scans	θmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker,2000)	h = −14→14
Tmin = 0.979, Tmax = 0.981	k = −7→7
6535 measured reflections	l = −21→18

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.030P)2] where P = (Fo2 + 2Fc2)/3
2566 reflections	(Δ/σ)max < 0.001
304 parameters	Δρmax = 0.13 e Å−3
1 restraint	Δρmin = −0.11 e Å−3

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 > 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
C1	0.1366 (3)	0.0950 (8)	0.1997 (2)	0.0617 (9)
H1	0.1843	0.0198	0.2426	0.074*
C2	0.0250 (3)	0.0040 (7)	0.1606 (2)	0.0610 (10)
H2	0.0002	−0.1319	0.1784	0.073*
C3	−0.0446 (3)	0.1107 (7)	0.0988 (2)	0.0658 (10)
H3	−0.1171	0.0486	0.0744	0.079*
C4	−0.0107 (3)	0.3060 (7)	0.0718 (2)	0.0644 (10)
H4	−0.0598	0.3783	0.0287	0.077*
C5	0.1006 (3)	0.4042 (7)	0.1088 (2)	0.0604 (9)
H5	0.1237	0.5395	0.0895	0.072*
C6	0.1729 (3)	0.2994 (6)	0.17230 (19)	0.0526 (8)
C7	0.2931 (2)	0.3938 (6)	0.20841 (16)	0.0479 (8)
H7	0.2980	0.5524	0.1912	0.058*
C8	0.3874 (3)	0.2465 (7)	0.18741 (17)	0.0520 (8)
H8	0.3854	0.0892	0.2065	0.062*
C9	0.3699 (2)	0.2474 (6)	0.10007 (17)	0.0454 (7)
C10	0.3172 (3)	0.0645 (7)	0.05519 (19)	0.0575 (9)
H10	0.2938	−0.0621	0.0790	0.069*
C11	0.2988 (3)	0.0677 (7)	−0.0256 (2)	0.0592 (9)
H11	0.2647	−0.0576	−0.0555	0.071*
C12	0.3315 (3)	0.2587 (7)	−0.06095 (19)	0.0545 (8)
H12	0.3165	0.2639	−0.1150	0.065*
C13	0.3855 (3)	0.4387 (7)	−0.01715 (19)	0.0560 (9)
H13	0.4093	0.5640	−0.0414	0.067*
C14	0.4059 (2)	0.4372 (6)	0.06493 (19)	0.0511 (8)
H14	0.4427	0.5604	0.0949	0.061*
C15	0.3427 (3)	0.5843 (7)	0.3341 (2)	0.0534 (8)
C16	0.3422 (3)	0.5479 (7)	0.4175 (2)	0.0586 (9)
C17	0.2955 (3)	0.3621 (7)	0.4423 (2)	0.0629 (10)
H17	0.2644	0.2469	0.4066	0.076*
C18	0.2919 (3)	0.3359 (7)	0.5200 (2)	0.0611 (10)
H18	0.2595	0.2051	0.5356	0.073*
C19	0.3806 (3)	0.6880 (6)	0.5480 (2)	0.0611 (10)
H19	0.4073	0.8048	0.5840	0.073*
C20	0.3910 (3)	0.7229 (7)	0.4693 (2)	0.0639 (10)
H20	0.4270	0.8507	0.4548	0.077*
C21	0.5955 (3)	0.2419 (6)	0.22411 (18)	0.0478 (8)
C22	0.7001 (3)	0.3845 (6)	0.25533 (17)	0.0504 (8)
C23	0.7001 (3)	0.5913 (7)	0.29022 (18)	0.0551 (9)
H23	0.6312	0.6513	0.2971	0.066*
C24	0.8028 (3)	0.7121 (7)	0.3155 (2)	0.0608 (10)
H24	0.8009	0.8528	0.3398	0.073*
C25	0.9004 (3)	0.4385 (8)	0.2745 (2)	0.0661 (10)
H25	0.9706	0.3818	0.2690	0.079*
C26	0.8048 (3)	0.2999 (7)	0.2472 (2)	0.0590 (9)
H26	0.8101	0.1579	0.2245	0.071*
N1	0.3370 (3)	0.5066 (6)	0.57225 (18)	0.0654 (8)
N2	0.9046 (3)	0.6389 (6)	0.30715 (18)	0.0660 (9)
O1	0.31042 (17)	0.3875 (4)	0.29344 (11)	0.0516 (6)
O2	0.36767 (19)	0.7536 (5)	0.30737 (14)	0.0629 (7)
O3	0.49642 (18)	0.3587 (4)	0.22757 (12)	0.0531 (6)
O4	0.59297 (19)	0.0481 (5)	0.19752 (13)	0.0587 (6)
O5	0.0848 (2)	0.9233 (6)	0.40864 (18)	0.0779 (9)
H5A	0.059 (4)	0.815 (9)	0.424 (3)	0.093*
H5B	0.047 (3)	0.947 (8)	0.362 (3)	0.093*

	U11	U22	U33	U12	U13	U23
C1	0.061 (2)	0.065 (3)	0.058 (2)	0.0020 (18)	0.0136 (18)	0.0043 (19)
C2	0.063 (2)	0.059 (3)	0.061 (2)	−0.0087 (17)	0.0178 (19)	−0.0038 (18)
C3	0.062 (2)	0.069 (3)	0.064 (2)	−0.010 (2)	0.0140 (19)	−0.015 (2)
C4	0.060 (2)	0.067 (3)	0.062 (2)	0.0080 (19)	0.0089 (18)	−0.005 (2)
C5	0.0522 (18)	0.063 (2)	0.064 (2)	0.0058 (18)	0.0123 (16)	−0.001 (2)
C6	0.0556 (19)	0.057 (2)	0.0475 (18)	−0.0030 (16)	0.0178 (15)	−0.0043 (17)
C7	0.0533 (17)	0.057 (2)	0.0308 (15)	0.0098 (16)	0.0067 (13)	0.0048 (15)
C8	0.0542 (18)	0.062 (2)	0.0420 (17)	−0.0031 (16)	0.0175 (15)	0.0039 (16)
C9	0.0432 (15)	0.053 (2)	0.0411 (18)	0.0037 (15)	0.0136 (14)	−0.0001 (16)
C10	0.0568 (19)	0.065 (2)	0.050 (2)	−0.0001 (18)	0.0130 (16)	−0.0030 (19)
C11	0.061 (2)	0.061 (2)	0.054 (2)	−0.0055 (19)	0.0127 (17)	−0.0121 (19)
C12	0.0562 (18)	0.067 (2)	0.0429 (19)	0.0085 (18)	0.0180 (16)	0.0023 (18)
C13	0.0502 (17)	0.064 (2)	0.0525 (19)	0.0065 (17)	0.0121 (15)	0.0081 (18)
C14	0.0488 (17)	0.059 (2)	0.0481 (18)	−0.0065 (17)	0.0179 (14)	−0.0004 (17)
C15	0.0568 (19)	0.052 (2)	0.053 (2)	0.0120 (17)	0.0188 (16)	0.0071 (19)
C16	0.064 (2)	0.062 (2)	0.0490 (18)	−0.0077 (18)	0.0140 (16)	−0.0006 (18)
C17	0.066 (2)	0.066 (3)	0.055 (2)	−0.0181 (18)	0.0140 (18)	−0.0070 (19)
C18	0.067 (2)	0.059 (2)	0.055 (2)	−0.0162 (18)	0.0121 (17)	0.0051 (18)
C19	0.065 (2)	0.060 (2)	0.057 (2)	−0.0133 (19)	0.0159 (17)	−0.0154 (19)
C20	0.0620 (19)	0.063 (2)	0.065 (2)	−0.0051 (18)	0.0138 (18)	−0.0064 (19)
C21	0.0522 (17)	0.058 (2)	0.0351 (16)	0.0071 (16)	0.0142 (14)	0.0124 (16)
C22	0.0616 (19)	0.060 (2)	0.0320 (15)	0.0033 (17)	0.0170 (14)	0.0072 (16)
C23	0.060 (2)	0.065 (3)	0.0394 (17)	0.0064 (17)	0.0124 (15)	0.0017 (17)
C24	0.060 (2)	0.063 (3)	0.058 (2)	0.0028 (18)	0.0136 (18)	−0.0088 (18)
C25	0.063 (2)	0.064 (3)	0.072 (2)	−0.001 (2)	0.0174 (19)	−0.011 (2)
C26	0.0579 (19)	0.061 (2)	0.058 (2)	−0.0075 (17)	0.0152 (17)	−0.0077 (18)
N1	0.0718 (19)	0.066 (2)	0.0574 (17)	−0.0158 (16)	0.0152 (15)	−0.0097 (16)
N2	0.0662 (18)	0.066 (2)	0.065 (2)	0.0032 (15)	0.0164 (15)	−0.0170 (17)
O1	0.0563 (13)	0.0607 (16)	0.0372 (12)	−0.0064 (12)	0.0117 (10)	0.0014 (11)
O2	0.0610 (14)	0.0649 (17)	0.0592 (15)	−0.0069 (13)	0.0100 (12)	0.0042 (14)
O3	0.0570 (12)	0.0594 (15)	0.0429 (11)	0.0088 (11)	0.0134 (10)	−0.0027 (11)
O4	0.0579 (13)	0.0690 (17)	0.0498 (13)	0.0184 (13)	0.0153 (10)	−0.0072 (13)
O5	0.0623 (17)	0.073 (2)	0.079 (2)	−0.0134 (15)	−0.0127 (14)	0.0160 (17)

C1—C6	1.399 (5)	C15—O2	1.168 (4)
C1—C2	1.427 (5)	C15—O1	1.354 (4)
C1—H1	0.9300	C15—C16	1.502 (5)
C2—C3	1.339 (5)	C16—C17	1.344 (5)
C2—H2	0.9300	C16—C20	1.392 (5)
C3—C4	1.339 (6)	C17—C18	1.402 (5)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.433 (5)	C18—N1	1.369 (5)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.367 (5)	C19—N1	1.302 (5)
C5—H5	0.9300	C19—C20	1.452 (5)
C6—C7	1.507 (4)	C19—H19	0.9300
C7—O1	1.471 (3)	C20—H20	0.9300
C7—C8	1.538 (4)	C21—O4	1.221 (5)
C7—H7	0.9800	C21—O3	1.379 (4)
C8—O3	1.459 (4)	C21—C22	1.477 (5)
C8—C9	1.511 (4)	C22—C23	1.355 (5)
C8—H8	0.9800	C22—C26	1.386 (4)
C9—C10	1.377 (5)	C23—C24	1.379 (5)
C9—C14	1.394 (5)	C23—H23	0.9300
C10—C11	1.394 (5)	C24—N2	1.333 (4)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.385 (5)	C25—N2	1.298 (5)
C11—H11	0.9300	C25—C26	1.374 (5)
C12—C13	1.361 (5)	C25—H25	0.9300
C12—H12	0.9300	C26—H26	0.9300
C13—C14	1.414 (5)	O5—H5A	0.78 (5)
C13—H13	0.9300	O5—H5B	0.84 (4)
C14—H14	0.9300
C6—C1—C2	118.9 (3)	C9—C14—C13	118.7 (3)
C6—C1—H1	120.6	C9—C14—H14	120.7
C2—C1—H1	120.6	C13—C14—H14	120.7
C3—C2—C1	121.2 (4)	O2—C15—O1	124.4 (3)
C3—C2—H2	119.4	O2—C15—C16	126.2 (4)
C1—C2—H2	119.4	O1—C15—C16	109.4 (3)
C4—C3—C2	120.6 (4)	C17—C16—C20	120.7 (3)
C4—C3—H3	119.7	C17—C16—C15	123.3 (3)
C2—C3—H3	119.7	C20—C16—C15	116.0 (4)
C3—C4—C5	120.4 (4)	C16—C17—C18	122.4 (3)
C3—C4—H4	119.8	C16—C17—H17	118.8
C5—C4—H4	119.8	C18—C17—H17	118.8
C6—C5—C4	120.1 (4)	N1—C18—C17	118.6 (3)
C6—C5—H5	119.9	N1—C18—H18	120.7
C4—C5—H5	119.9	C17—C18—H18	120.7
C5—C6—C1	118.8 (3)	N1—C19—C20	125.3 (3)
C5—C6—C7	120.3 (3)	N1—C19—H19	117.3
C1—C6—C7	120.7 (3)	C20—C19—H19	117.3
O1—C7—C6	106.5 (2)	C16—C20—C19	113.9 (4)
O1—C7—C8	109.0 (2)	C16—C20—H20	123.0
C6—C7—C8	111.5 (3)	C19—C20—H20	123.0
O1—C7—H7	109.9	O4—C21—O3	122.8 (3)
C6—C7—H7	109.9	O4—C21—C22	126.6 (3)
C8—C7—H7	109.9	O3—C21—C22	110.6 (3)
O3—C8—C9	111.1 (2)	C23—C22—C26	118.4 (3)
O3—C8—C7	104.2 (3)	C23—C22—C21	124.6 (3)
C9—C8—C7	109.9 (3)	C26—C22—C21	117.0 (3)
O3—C8—H8	110.5	C22—C23—C24	119.6 (3)
C9—C8—H8	110.5	C22—C23—H23	120.2
C7—C8—H8	110.5	C24—C23—H23	120.2
C10—C9—C14	120.1 (3)	N2—C24—C23	123.8 (4)
C10—C9—C8	120.6 (3)	N2—C24—H24	118.1
C14—C9—C8	119.3 (3)	C23—C24—H24	118.1
C9—C10—C11	120.5 (4)	N2—C25—C26	128.0 (4)
C9—C10—H10	119.7	N2—C25—H25	116.0
C11—C10—H10	119.7	C26—C25—H25	116.0
C12—C11—C10	119.6 (3)	C25—C26—C22	116.0 (3)
C12—C11—H11	120.2	C25—C26—H26	122.0
C10—C11—H11	120.2	C22—C26—H26	122.0
C13—C12—C11	120.5 (3)	C19—N1—C18	118.9 (3)
C13—C12—H12	119.8	C25—N2—C24	114.2 (4)
C11—C12—H12	119.8	C15—O1—C7	117.9 (3)
C12—C13—C14	120.6 (3)	C21—O3—C8	114.7 (3)
C12—C13—H13	119.7	H5A—O5—H5B	108 (4)
C14—C13—H13	119.7

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···N2i	0.84 (4)	2.48 (5)	2.921 (4)	113 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5B⋯N2i	0.84 (4)	2.48 (5)	2.921 (4)	113 (4)

Symmetry code: (i) .