3'-Benz-yloxy-3-hydr-oxy-3,3'-bi-1H-indole-2,2'(3H,3'H)-dione monohydrate.

In the title compound, C(23)H(18)N(2)O(4)·H(2)O, the two oxindole rings subtend a dihedral angle of 54.29 (5)°. The crystal structure is stabilized by intermolecular N-H⋯O, O-H⋯O and C-H⋯π inter-actions.

Related literature

For the biological activity and pharmaceutical applications of indole derivatives, see: Harris & Uhle (1960 ▶); Ho et al. (1986 ▶); Rajeswaran et al. (1999 ▶); Stevenson et al. (2000 ▶). For description of hydrogen-bond motifs, see Bernstein et al. (1995 ▶).

Experimental

Crystal data

C23H18N2O4·H2O

M = 404.41

Triclinic,

a = 9.8243 (3) Å

b = 9.9304 (6) Å

c = 11.4460 (5) Å

α = 107.517 (2)°

β = 114.227 (3)°

γ = 93.918 (2)°

V = 947.17 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.28 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.972, T max = 0.980

16894 measured reflections

3335 independent reflections

3045 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.084

S = 1.05

3335 reflections

292 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); 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: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012380/bt2889sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012380/bt2889Isup2.hkl

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

C23H18N2O4·H2O	Z = 2
Mr = 404.41	F(000) = 424
Triclinic, P1	Dx = 1.418 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8243 (3) Å	Cell parameters from 4635 reflections
b = 9.9304 (6) Å	θ = 2.1–25.0°
c = 11.4460 (5) Å	µ = 0.10 mm−1
α = 107.517 (2)°	T = 293 K
β = 114.227 (3)°	Block, colourless
γ = 93.918 (2)°	0.28 × 0.25 × 0.20 mm
V = 947.17 (8) Å3

Bruker Kappa APEXII area-detector diffractometer	3335 independent reflections
Radiation source: fine-focus sealed tube	3045 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω and φ scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −11→11
Tmin = 0.972, Tmax = 0.980	k = −11→11
16894 measured reflections	l = −13→13

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)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084	w = 1/[σ2(Fo2) + (0.038P)2 + 0.3004P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.003
3335 reflections	Δρmax = 0.23 e Å−3
292 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.038 (3)

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	0.33868 (11)	0.37105 (9)	0.58225 (10)	0.0399 (2)
O2	0.38716 (10)	0.07924 (10)	0.53420 (9)	0.0335 (2)
H2	0.381 (2)	−0.018 (2)	0.504 (2)	0.070 (6)*
O3	0.61939 (10)	0.21310 (10)	0.48237 (10)	0.0374 (2)
O4	0.33920 (10)	0.00510 (8)	0.25071 (9)	0.0302 (2)
O5	0.09912 (16)	−0.40448 (16)	−0.55511 (16)	0.0632 (3)
H5B	0.183 (4)	−0.346 (3)	−0.552 (3)	0.129 (10)*
H5A	0.064 (4)	−0.482 (4)	−0.622 (3)	0.135 (12)*
N1	0.09503 (13)	0.23295 (12)	0.47470 (12)	0.0349 (3)
H1	0.0522 (19)	0.2945 (18)	0.5098 (17)	0.048 (4)*
C2	0.02036 (14)	0.08934 (14)	0.38791 (13)	0.0320 (3)
C3	−0.12940 (15)	0.02332 (17)	0.34058 (15)	0.0435 (3)
H3	−0.1961	0.0735	0.3647	0.052*
C4	−0.17671 (17)	−0.12064 (19)	0.25573 (16)	0.0520 (4)
H4	−0.2777	−0.1681	0.2211	0.062*
C5	−0.07767 (19)	−0.19539 (17)	0.22128 (17)	0.0521 (4)
H5	−0.1129	−0.2921	0.1632	0.062*
C6	0.07409 (17)	−0.12838 (15)	0.27202 (14)	0.0407 (3)
H6	0.1416	−0.1794	0.2502	0.049*
C7	0.12222 (14)	0.01554 (13)	0.35540 (12)	0.0288 (3)
C8	0.27766 (13)	0.11694 (12)	0.43061 (12)	0.0262 (3)
C9	0.24378 (14)	0.25831 (13)	0.50590 (12)	0.0286 (3)
C10	0.33824 (13)	0.14368 (12)	0.33172 (12)	0.0255 (3)
C11	0.50226 (13)	0.24303 (12)	0.41187 (12)	0.0273 (3)
N12	0.49318 (12)	0.36457 (11)	0.38326 (11)	0.0305 (2)
H12	0.5721 (18)	0.4358 (17)	0.4159 (16)	0.042 (4)*
C13	0.34446 (14)	0.36220 (13)	0.29098 (12)	0.0289 (3)
C14	0.29438 (16)	0.46934 (14)	0.24218 (14)	0.0382 (3)
H14	0.3602	0.5570	0.2701	0.046*
C15	0.14143 (18)	0.44063 (16)	0.14958 (15)	0.0448 (4)
H15	0.1036	0.5108	0.1147	0.054*
C16	0.04399 (16)	0.31071 (17)	0.10790 (15)	0.0443 (4)
H16	−0.0580	0.2940	0.0447	0.053*
C17	0.09647 (15)	0.20413 (15)	0.15937 (13)	0.0359 (3)
H17	0.0307	0.1164	0.1314	0.043*
C18	0.24816 (14)	0.23153 (13)	0.25278 (12)	0.0277 (3)
C19	0.40617 (18)	0.00789 (15)	0.16166 (15)	0.0418 (3)
H19A	0.5160	0.0441	0.2151	0.050*
H19B	0.3649	0.0719	0.1131	0.050*
C20	0.37193 (14)	−0.14144 (13)	0.06125 (13)	0.0315 (3)
C21	0.39451 (15)	−0.25784 (15)	0.10387 (14)	0.0370 (3)
H21	0.4291	−0.2440	0.1963	0.044*
C22	0.36598 (19)	−0.39435 (16)	0.00986 (17)	0.0492 (4)
H22	0.3802	−0.4725	0.0390	0.059*
C23	0.3165 (2)	−0.41584 (17)	−0.12678 (18)	0.0573 (4)
H23	0.2985	−0.5080	−0.1897	0.069*
C24	0.2940 (2)	−0.30139 (19)	−0.16987 (16)	0.0566 (4)
H24	0.2607	−0.3157	−0.2623	0.068*
C25	0.32036 (17)	−0.16459 (17)	−0.07653 (15)	0.0440 (3)
H25	0.3033	−0.0874	−0.1067	0.053*

	U11	U22	U33	U12	U13	U23
O1	0.0466 (6)	0.0270 (5)	0.0427 (5)	0.0014 (4)	0.0243 (5)	0.0037 (4)
O2	0.0331 (5)	0.0333 (5)	0.0335 (5)	0.0095 (4)	0.0121 (4)	0.0154 (4)
O3	0.0245 (5)	0.0340 (5)	0.0483 (6)	0.0061 (4)	0.0110 (4)	0.0158 (4)
O4	0.0346 (5)	0.0230 (4)	0.0360 (5)	0.0038 (3)	0.0224 (4)	0.0061 (4)
O5	0.0581 (8)	0.0594 (8)	0.0800 (9)	0.0163 (6)	0.0439 (7)	0.0168 (7)
N1	0.0346 (6)	0.0360 (6)	0.0414 (6)	0.0138 (5)	0.0235 (5)	0.0135 (5)
C2	0.0298 (6)	0.0400 (7)	0.0316 (6)	0.0074 (5)	0.0149 (5)	0.0187 (6)
C3	0.0279 (7)	0.0621 (9)	0.0482 (8)	0.0095 (6)	0.0179 (6)	0.0292 (7)
C4	0.0302 (7)	0.0672 (11)	0.0510 (9)	−0.0090 (7)	0.0111 (7)	0.0258 (8)
C5	0.0502 (9)	0.0427 (8)	0.0482 (9)	−0.0148 (7)	0.0180 (7)	0.0082 (7)
C6	0.0428 (8)	0.0333 (7)	0.0433 (8)	−0.0011 (6)	0.0219 (7)	0.0089 (6)
C7	0.0282 (6)	0.0306 (6)	0.0293 (6)	0.0026 (5)	0.0139 (5)	0.0125 (5)
C8	0.0256 (6)	0.0250 (6)	0.0283 (6)	0.0057 (5)	0.0123 (5)	0.0096 (5)
C9	0.0332 (7)	0.0277 (6)	0.0296 (6)	0.0076 (5)	0.0174 (5)	0.0117 (5)
C10	0.0247 (6)	0.0217 (6)	0.0288 (6)	0.0041 (4)	0.0132 (5)	0.0064 (5)
C11	0.0257 (6)	0.0253 (6)	0.0304 (6)	0.0055 (5)	0.0145 (5)	0.0070 (5)
N12	0.0265 (5)	0.0251 (5)	0.0359 (6)	0.0003 (4)	0.0123 (5)	0.0096 (4)
C13	0.0311 (6)	0.0290 (6)	0.0279 (6)	0.0066 (5)	0.0152 (5)	0.0095 (5)
C14	0.0458 (8)	0.0319 (7)	0.0389 (7)	0.0085 (6)	0.0185 (6)	0.0164 (6)
C15	0.0505 (9)	0.0480 (8)	0.0432 (8)	0.0204 (7)	0.0189 (7)	0.0272 (7)
C16	0.0328 (7)	0.0612 (9)	0.0389 (8)	0.0134 (7)	0.0110 (6)	0.0247 (7)
C17	0.0290 (7)	0.0431 (7)	0.0334 (7)	0.0037 (6)	0.0119 (5)	0.0151 (6)
C18	0.0289 (6)	0.0293 (6)	0.0269 (6)	0.0061 (5)	0.0152 (5)	0.0092 (5)
C19	0.0520 (8)	0.0333 (7)	0.0501 (8)	0.0037 (6)	0.0375 (7)	0.0089 (6)
C20	0.0287 (6)	0.0326 (7)	0.0353 (7)	0.0053 (5)	0.0194 (5)	0.0084 (5)
C21	0.0376 (7)	0.0400 (7)	0.0350 (7)	0.0105 (6)	0.0179 (6)	0.0129 (6)
C22	0.0611 (10)	0.0361 (8)	0.0614 (10)	0.0175 (7)	0.0380 (8)	0.0161 (7)
C23	0.0735 (11)	0.0402 (8)	0.0540 (10)	0.0033 (8)	0.0412 (9)	−0.0039 (7)
C24	0.0673 (11)	0.0638 (11)	0.0328 (8)	0.0027 (8)	0.0273 (8)	0.0056 (7)
C25	0.0499 (9)	0.0494 (8)	0.0409 (8)	0.0117 (7)	0.0253 (7)	0.0201 (7)

O1—C9	1.2191 (15)	N12—C13	1.4016 (16)
O2—C8	1.4066 (14)	N12—H12	0.877 (16)
O2—H2	0.91 (2)	C13—C14	1.3747 (18)
O3—C11	1.2218 (15)	C13—C18	1.3861 (17)
O4—C10	1.4123 (14)	C14—C15	1.384 (2)
O4—C19	1.4273 (15)	C14—H14	0.9300
O5—H5B	0.96 (3)	C15—C16	1.376 (2)
O5—H5A	0.83 (3)	C15—H15	0.9300
N1—C9	1.3392 (17)	C16—C17	1.391 (2)
N1—C2	1.4017 (17)	C16—H16	0.9300
N1—H1	0.860 (18)	C17—C18	1.3783 (18)
C2—C3	1.3742 (19)	C17—H17	0.9300
C2—C7	1.3851 (18)	C19—C20	1.4906 (18)
C3—C4	1.381 (2)	C19—H19A	0.9700
C3—H3	0.9300	C19—H19B	0.9700
C4—C5	1.375 (2)	C20—C25	1.3808 (19)
C4—H4	0.9300	C20—C21	1.3816 (19)
C5—C6	1.387 (2)	C21—C22	1.377 (2)
C5—H5	0.9300	C21—H21	0.9300
C6—C7	1.3759 (18)	C22—C23	1.374 (2)
C6—H6	0.9300	C22—H22	0.9300
C7—C8	1.5086 (16)	C23—C24	1.366 (3)
C8—C9	1.5477 (16)	C23—H23	0.9300
C8—C10	1.5551 (16)	C24—C25	1.380 (2)
C10—C18	1.5114 (17)	C24—H24	0.9300
C10—C11	1.5608 (16)	C25—H25	0.9300
C11—N12	1.3418 (16)
C8—O2—H2	110.3 (12)	C13—N12—H12	123.8 (10)
C10—O4—C19	113.84 (9)	C14—C13—C18	122.68 (12)
H5B—O5—H5A	112 (3)	C14—C13—N12	127.59 (12)
C9—N1—C2	111.86 (11)	C18—C13—N12	109.73 (11)
C9—N1—H1	124.2 (11)	C13—C14—C15	116.90 (13)
C2—N1—H1	123.7 (11)	C13—C14—H14	121.5
C3—C2—C7	122.20 (13)	C15—C14—H14	121.5
C3—C2—N1	127.96 (13)	C16—C15—C14	121.59 (13)
C7—C2—N1	109.82 (11)	C16—C15—H15	119.2
C2—C3—C4	117.24 (14)	C14—C15—H15	119.2
C2—C3—H3	121.4	C15—C16—C17	120.67 (13)
C4—C3—H3	121.4	C15—C16—H16	119.7
C5—C4—C3	121.41 (13)	C17—C16—H16	119.7
C5—C4—H4	119.3	C18—C17—C16	118.49 (12)
C3—C4—H4	119.3	C18—C17—H17	120.8
C4—C5—C6	120.82 (14)	C16—C17—H17	120.8
C4—C5—H5	119.6	C17—C18—C13	119.65 (12)
C6—C5—H5	119.6	C17—C18—C10	131.70 (11)
C7—C6—C5	118.33 (14)	C13—C18—C10	108.63 (10)
C7—C6—H6	120.8	O4—C19—C20	109.22 (10)
C5—C6—H6	120.8	O4—C19—H19A	109.8
C6—C7—C2	119.98 (12)	C20—C19—H19A	109.8
C6—C7—C8	131.53 (12)	O4—C19—H19B	109.8
C2—C7—C8	108.41 (10)	C20—C19—H19B	109.8
O2—C8—C7	114.09 (10)	H19A—C19—H19B	108.3
O2—C8—C9	105.88 (9)	C25—C20—C21	118.92 (12)
C7—C8—C9	101.76 (9)	C25—C20—C19	119.93 (13)
O2—C8—C10	111.95 (9)	C21—C20—C19	121.13 (12)
C7—C8—C10	112.73 (9)	C22—C21—C20	120.20 (13)
C9—C8—C10	109.61 (9)	C22—C21—H21	119.9
O1—C9—N1	126.95 (12)	C20—C21—H21	119.9
O1—C9—C8	124.94 (11)	C23—C22—C21	120.39 (15)
N1—C9—C8	108.10 (10)	C23—C22—H22	119.8
O4—C10—C18	115.50 (9)	C21—C22—H22	119.8
O4—C10—C8	105.35 (9)	C24—C23—C22	119.82 (14)
C18—C10—C8	112.18 (9)	C24—C23—H23	120.1
O4—C10—C11	110.65 (9)	C22—C23—H23	120.1
C18—C10—C11	101.56 (9)	C23—C24—C25	120.11 (14)
C8—C10—C11	111.77 (9)	C23—C24—H24	119.9
O3—C11—N12	125.87 (11)	C25—C24—H24	119.9
O3—C11—C10	126.42 (11)	C24—C25—C20	120.55 (14)
N12—C11—C10	107.61 (10)	C24—C25—H25	119.7
C11—N12—C13	112.33 (10)	C20—C25—H25	119.7
C11—N12—H12	123.8 (10)
C9—N1—C2—C3	176.59 (13)	O4—C10—C11—O3	−50.44 (16)
C9—N1—C2—C7	−2.02 (15)	C18—C10—C11—O3	−173.59 (12)
C7—C2—C3—C4	−1.4 (2)	C8—C10—C11—O3	66.64 (15)
N1—C2—C3—C4	−179.82 (13)	O4—C10—C11—N12	126.13 (10)
C2—C3—C4—C5	0.7 (2)	C18—C10—C11—N12	2.99 (12)
C3—C4—C5—C6	0.6 (2)	C8—C10—C11—N12	−116.79 (11)
C4—C5—C6—C7	−1.3 (2)	O3—C11—N12—C13	175.33 (12)
C5—C6—C7—C2	0.7 (2)	C10—C11—N12—C13	−1.27 (13)
C5—C6—C7—C8	177.20 (13)	C11—N12—C13—C14	178.62 (12)
C3—C2—C7—C6	0.65 (19)	C11—N12—C13—C18	−1.22 (14)
N1—C2—C7—C6	179.35 (11)	C18—C13—C14—C15	−1.10 (19)
C3—C2—C7—C8	−176.58 (11)	N12—C13—C14—C15	179.07 (12)
N1—C2—C7—C8	2.12 (14)	C13—C14—C15—C16	−0.2 (2)
C6—C7—C8—O2	−64.69 (17)	C14—C15—C16—C17	0.8 (2)
C2—C7—C8—O2	112.10 (11)	C15—C16—C17—C18	−0.1 (2)
C6—C7—C8—C9	−178.23 (13)	C16—C17—C18—C13	−1.14 (19)
C2—C7—C8—C9	−1.44 (12)	C16—C17—C18—C10	176.85 (12)
C6—C7—C8—C10	64.46 (17)	C14—C13—C18—C17	1.79 (19)
C2—C7—C8—C10	−118.75 (11)	N12—C13—C18—C17	−178.35 (11)
C2—N1—C9—O1	−177.54 (12)	C14—C13—C18—C10	−176.62 (11)
C2—N1—C9—C8	1.01 (14)	N12—C13—C18—C10	3.23 (13)
O2—C8—C9—O1	59.33 (15)	O4—C10—C18—C17	58.38 (17)
C7—C8—C9—O1	178.85 (11)	C8—C10—C18—C17	−62.37 (16)
C10—C8—C9—O1	−61.60 (15)	C11—C10—C18—C17	178.15 (13)
O2—C8—C9—N1	−119.26 (10)	O4—C10—C18—C13	−123.47 (11)
C7—C8—C9—N1	0.27 (12)	C8—C10—C18—C13	115.79 (11)
C10—C8—C9—N1	119.82 (11)	C11—C10—C18—C13	−3.70 (12)
C19—O4—C10—C18	61.51 (14)	C10—O4—C19—C20	−168.10 (10)
C19—O4—C10—C8	−174.11 (10)	O4—C19—C20—C25	133.58 (13)
C19—O4—C10—C11	−53.14 (13)	O4—C19—C20—C21	−48.07 (17)
O2—C8—C10—O4	73.14 (11)	C25—C20—C21—C22	0.1 (2)
C7—C8—C10—O4	−57.10 (12)	C19—C20—C21—C22	−178.29 (13)
C9—C8—C10—O4	−169.68 (9)	C20—C21—C22—C23	0.7 (2)
O2—C8—C10—C18	−160.41 (9)	C21—C22—C23—C24	−0.7 (3)
C7—C8—C10—C18	69.34 (12)	C22—C23—C24—C25	−0.1 (3)
C9—C8—C10—C18	−43.23 (13)	C23—C24—C25—C20	1.0 (3)
O2—C8—C10—C11	−47.09 (13)	C21—C20—C25—C24	−0.9 (2)
C7—C8—C10—C11	−177.34 (9)	C19—C20—C25—C24	177.44 (14)
C9—C8—C10—C11	70.09 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5i	0.860 (18)	2.045 (18)	2.8858 (17)	165.6 (15)
O2—H2···O3ii	0.91 (2)	1.99 (2)	2.8463 (13)	155.9 (18)
O2—H2···O2ii	0.91 (2)	2.57 (2)	3.0274 (18)	111.9 (14)
O5—H5B···O3iii	0.96 (3)	1.97 (3)	2.8969 (17)	161 (3)
N12—H12···O1iv	0.877 (16)	2.044 (16)	2.8329 (14)	149.2 (14)
C17—H17···Cg3	0.93	3.15	3.8226 (17)	131
C16—H16···Cg5v	0.93	2.75	3.5140 (19)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5i	0.860 (18)	2.045 (18)	2.8858 (17)	165.6 (15)
O2—H2⋯O3ii	0.91 (2)	1.99 (2)	2.8463 (13)	155.9 (18)
O2—H2⋯O2ii	0.91 (2)	2.57 (2)	3.0274 (18)	111.9 (14)
O5—H5B⋯O3iii	0.96 (3)	1.97 (3)	2.8969 (17)	161 (3)
N12—H12⋯O1iv	0.877 (16)	2.044 (16)	2.8329 (14)	149.2 (14)
C17—H17⋯Cg3	0.93	3.15	3.8226 (17)	130
C16—H16⋯Cg5v	0.93	2.75	3.5140 (19)	140

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg3 is the centroid of the C2–C7 ring and Cg5 is the centroid of the C20–C25 ring.