3′-Benz­yloxy-3-hydr­oxy-3,3′-bi-1H-indole-2,2′(3H,3′H)-dione monohydrate

Ramesh, P.; Sundaresan, S.S.; Lakshmi, N.V.; Perumal, P.T.; Ponnuswamy, M.N.

doi:10.1107/S1600536809012380

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o994

doi:10.1107/S1600536809012380

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3′-Benzyloxy-3-hydroxy-3,3′-bi-1H-indole-2,2′(3H,3′H)-dione monohydrate

P. Ramesh,^a S. S. Sundaresan,^b N. Vidhya Lakshmi,^c Paramasivan T. Perumal ^c and M. N. Ponnuswamy ^b ^*

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, ^bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^cOrganic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 600 020, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 28 February 2009; accepted 2 April 2009; online 8 April 2009)

In the title compound, C₂₃H₁₈N₂O₄·H₂O, 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 interactions.

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_r = 404.41
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.032
wR(F²) = 0.084
S = 1.05
3335 reflections
292 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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⋯O1^iv	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⋯Cg5^v	0.93	2.75	3.5140 (19)	140
Symmetry codes: (i) -x, -y, -z; (ii) -x+1, -y, -z+1; (iii) -x+1, -y, -z; (iv) -x+1, -y+1, -z+1; (v) -x, -y, -z. Cg3 is the centroid of the C2–C7 ring and Cg5 is the centroid of the C20–C25 ring.

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 ).

Supporting information

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

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

checkCIF report

Comment top

Indole derivatives are used as bioactive drugs (Stevenson et al., 2000) and they exibit anti-allergic, central nervous system depressant and muscle relaxant properties (Harris & Uhle 1960; Ho et al., 1986). Indoles have been proved to display high aldose reductase inhibitory activity (Rajeswaran et al., 1999). Against this background and to ascertain the molecular conformation, the structure determination of the title compound has been carried out.

The ORTEP plot of the molecule is shown in Fig. 1. The oxindole rings enclose a dihedral angle of 54.29 (5)°. In the benzene ring of the indole ring system, the endocyclic angels at C3 and C14 are contracted to 117.24 (25)° and 116.90 (14)°, while those at C2 and C13 are expanded to 122.20 (14)° and 122.69 (13)°, respectively. This would appear to be a real effect caused by the fusion of the pyrrole with benzene ring resulting in an angular distortion. The sum of the bond angles around the hetero nitrogen atom in the oxindole ring systems are equal to N1 [359.76 (11)°] and N12 [359.93 (10)°], is in accordance with the sp² hybridization.

The packing of the molecules in the crystal structure is stabilized through N-H···O, O-H···O and C-H···π interactions. Atom N12 (x, y, z) donates a proton to O1 (-x+1, -y+1, -z+1) and forms a dimer with graph-set motif of R²₂(14) (Bernstein et al., 1995). The intermolecular N1-H1···O5 and O5-H5B···O3 hydrogen bonds form a one dimensional chain running along a-axis. The indole ring interacts with the other indole moiety through a weak intra C-H···π interaction involving atom C17, the separation between H17 and the centroid of the C2/C3/C4/C5/C6/C7 (Cg3) ring being 3.15Å.

Related literature top

For related literature, see: Harris & Uhle (1960); Ho et al. (1986); Rajeswaran et al. (1999); Stevenson et al. (2000). For description of hydrogen bonds, see Bernstein et al. (1995). Cg3 ids the centroid of the C2–C7 ring and Cg5 is the centroid of the C20–C25 ring.

Experimental top

To a refluxing solution of isatin (1 equivalent), Rh₂(OAC)₄ (0.01 equivalent) in dichloromethane, benzyl alcohol (1.2 equivalent) was added. After five minutes, 3-diazo-1,3-dihydro-indol-2-one in dichloromethane was added dropwise through a syringe pump. The reaction mixture was allowed to stir at 60°C for half-an-hour. The solid formed in the reaction was filtered and washed with methanol to obtain the pure product. The compound was recrystallized in ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Perspective view of the molecule with displacement ellipsoids drawn at the 50% probability level. The H atoms are shown as small circles of arbitrary radii.
	Fig. 2. The crystal packing of the molecules viewed down c axis. H atoms not involved in hydrogen bonding have been omitted for clarity.

3'-Benzyloxy-3-hydroxy-3,3'-bi-1H-indole-2,2'(3H,3'H)-dione monohydrate top

Crystal data top

C₂₃H₁₈N₂O₄·H₂O	Z = 2
M_r = 404.41	F(000) = 424
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.038P)² + 0.3004P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.003
3335 reflections	Δρ_max = 0.23 e Å⁻³
292 parameters	Δρ_min = −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)

Crystal data top

C₂₃H₁₈N₂O₄·H₂O	γ = 93.918 (2)°
M_r = 404.41	V = 947.17 (8) Å³
Triclinic, P1	Z = 2
a = 9.8243 (3) Å	Mo Kα radiation
b = 9.9304 (6) Å	µ = 0.10 mm⁻¹
c = 11.4460 (5) Å	T = 293 K
α = 107.517 (2)°	0.28 × 0.25 × 0.20 mm
β = 114.227 (3)°

Data collection top

Bruker Kappa APEXII area-detector diffractometer	3335 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3045 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.980	R_int = 0.021
16894 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.23 e Å⁻³
3335 reflections	Δρ_min = −0.18 e Å⁻³
292 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O1^iv	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···Cg5ⁱ	0.93	2.75	3.5140 (19)	140

Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y, −z+1; (iii) −x+1, −y, −z; (iv) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₈N₂O₄·H₂O
M_r	404.41
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.8243 (3), 9.9304 (6), 11.4460 (5)
α, β, γ (°)	107.517 (2), 114.227 (3), 93.918 (2)
V (Å³)	947.17 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.28 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.972, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	16894, 3335, 3045
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.084, 1.05
No. of reflections	3335
No. of parameters	292
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.18

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.877 (16)	2.044 (16)	2.8329 (14)	149.2 (14)
C17—H17···Cg3	0.93	3.1532	3.8226 (17)	130.45
C16—H16···Cg5ⁱ	0.93	2.7483	3.5140 (19)	140.25

Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y, −z+1; (iii) −x+1, −y, −z; (iv) −x+1, −y+1, −z+1.

Acknowledgements

PR thanks Dr Babu Varghese, SAIF, IIT-Madras, India, for his help with the data collection.

References

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