2'-Amino-3,6-dihydroxyxanthene-9-spiro-1'-isoindolin-3'-one monohydrate.

The title compound, C(20)H(14)N(2)O(4)·H(2)O, was synthesized by the reaction of fluorescein and hydrazine hydrate in ethanol. In the crystal structure, the organic mol-ecules are linked into extended two-dimensional networks by inter-molecular hydrogen bonding. Additional face-to-face π-π stacking inter-actions between the phenolic benzene rings in two adjacent mol-ecules [centroid-to-centroid separation = 3.773 (3) Å] link the mol-ecules into a three-dimensional framework.

Related literature

For general background, see: Chen et al. (2006 ▶); Yang et al. (2005 ▶); Adamczyk et al. (2000 ▶). For related literature, see: Orndorff et al. (1927 ▶).

Experimental

Crystal data

C20H14N2O4·H2O

M = 364.35

Triclinic,

a = 7.8524 (9) Å

b = 10.7077 (13) Å

c = 11.2137 (13) Å

α = 103.857 (2)°

β = 110.432 (2)°

γ = 99.704 (2)°

V = 824.22 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 293 (2) K

0.32 × 0.26 × 0.22 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.967, T max = 0.977

4192 measured reflections

2892 independent reflections

1975 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.161

S = 1.01

2892 reflections

256 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT-Plus (Bruker, 1997 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Bruker, 1997 ▶); software used to prepare material for publication: SHELXTL (Bruker, 1997 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808000032/at2528sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000032/at2528Isup2.hkl

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

C20H14N2O4·H2O	Z = 2
Mr = 364.35	F000 = 380
Triclinic, P1	Dx = 1.468 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.8524 (9) Å	Cell parameters from 988 reflections
b = 10.7077 (13) Å	θ = 2.4–24.3º
c = 11.2137 (13) Å	µ = 0.11 mm−1
α = 103.857 (2)º	T = 293 (2) K
β = 110.432 (2)º	Block, light orange
γ = 99.704 (2)º	0.32 × 0.26 × 0.22 mm
V = 824.22 (17) Å3

Bruker SAMRT Apex CCD area-detector diffractometer	2892 independent reflections
Radiation source: sealed tube	1975 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
T = 293(2) K	θmax = 25.1º
phi and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Bruker, 1997)	h = −9→8
Tmin = 0.967, Tmax = 0.977	k = −12→12
4192 measured reflections	l = −11→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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.161	w = 1/[σ2(Fo2) + (0.0787P)2 + 0.372P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2892 reflections	Δρmax = 0.23 e Å−3
256 parameters	Δρmin = −0.21 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
C1	0.7582 (4)	0.8546 (3)	1.0078 (3)	0.0383 (7)
C2	0.8972 (4)	0.7821 (3)	0.9920 (3)	0.0363 (7)
C3	1.0760 (4)	0.7941 (3)	1.0832 (3)	0.0480 (8)
H3	1.1261	0.8547	1.1699	0.058*
C4	1.1785 (4)	0.7131 (3)	1.0418 (3)	0.0537 (9)
H4	1.2993	0.7193	1.1012	0.064*
C5	1.1019 (4)	0.6226 (3)	0.9121 (3)	0.0514 (8)
H5	1.1725	0.5688	0.8859	0.062*
C6	0.9215 (4)	0.6111 (3)	0.8207 (3)	0.0425 (7)
H6	0.8709	0.5510	0.7337	0.051*
C7	0.8206 (4)	0.6910 (3)	0.8629 (3)	0.0342 (6)
C8	0.6212 (4)	0.6958 (2)	0.7840 (2)	0.0323 (6)
C9	0.4728 (4)	0.5651 (3)	0.7417 (2)	0.0322 (6)
C10	0.4807 (4)	0.4862 (3)	0.8257 (3)	0.0375 (7)
H10	0.5825	0.5137	0.9089	0.045*
C11	0.3430 (4)	0.3696 (3)	0.7891 (3)	0.0409 (7)
H11	0.3522	0.3195	0.8471	0.049*
C12	0.1896 (4)	0.3268 (3)	0.6649 (3)	0.0398 (7)
C13	0.1775 (4)	0.4022 (3)	0.5803 (3)	0.0426 (7)
H13	0.0753	0.3747	0.4973	0.051*
C14	0.3180 (4)	0.5193 (3)	0.6192 (3)	0.0354 (6)
C15	0.4389 (4)	0.6917 (3)	0.5467 (3)	0.0340 (6)
C16	0.4123 (4)	0.7408 (3)	0.4402 (3)	0.0384 (7)
H16	0.3018	0.7034	0.3621	0.046*
C17	0.5519 (4)	0.8459 (3)	0.4512 (3)	0.0372 (7)
C18	0.7171 (4)	0.9011 (3)	0.5690 (3)	0.0415 (7)
H18	0.8112	0.9723	0.5770	0.050*
C19	0.7401 (4)	0.8499 (3)	0.6729 (3)	0.0399 (7)
H19	0.8511	0.8870	0.7507	0.048*
C20	0.6026 (4)	0.7444 (2)	0.6654 (2)	0.0332 (6)
N1	0.4419 (4)	0.8470 (3)	0.8590 (3)	0.0480 (7)
N2	0.6013 (3)	0.7991 (2)	0.8911 (2)	0.0360 (6)
O1	0.7722 (3)	0.9475 (2)	1.1028 (2)	0.0588 (7)
O2	0.0591 (3)	0.2089 (2)	0.6320 (2)	0.0560 (6)
H2	−0.0062	0.1822	0.5509	0.084*
O3	0.2926 (3)	0.5867 (2)	0.52644 (19)	0.0460 (6)
O4	0.5213 (3)	0.8911 (2)	0.34392 (19)	0.0501 (6)
H4A	0.6073	0.9578	0.3637	0.075*
O1W	0.1874 (3)	0.9043 (2)	0.6353 (2)	0.0548 (6)
H1A	0.379 (6)	0.820 (4)	0.896 (4)	0.072 (14)*
H1B	0.481 (4)	0.936 (3)	0.889 (2)	0.091 (14)*
H1WA	0.2675	0.8615	0.6600	0.16 (3)*
H1WB	0.1586	0.9439	0.7003	0.13 (2)*

	U11	U22	U33	U12	U13	U23
C1	0.0487 (17)	0.0328 (14)	0.0279 (14)	0.0084 (13)	0.0136 (13)	0.0054 (12)
C2	0.0392 (16)	0.0332 (14)	0.0284 (14)	0.0057 (12)	0.0089 (12)	0.0061 (11)
C3	0.0485 (18)	0.0438 (17)	0.0339 (16)	0.0090 (15)	0.0035 (14)	0.0043 (13)
C4	0.0378 (17)	0.063 (2)	0.0484 (19)	0.0163 (16)	0.0036 (15)	0.0157 (16)
C5	0.0401 (18)	0.0547 (19)	0.055 (2)	0.0219 (15)	0.0148 (15)	0.0115 (15)
C6	0.0410 (17)	0.0423 (16)	0.0359 (15)	0.0126 (14)	0.0117 (13)	0.0034 (13)
C7	0.0353 (15)	0.0317 (14)	0.0300 (14)	0.0065 (12)	0.0095 (12)	0.0078 (11)
C8	0.0351 (15)	0.0309 (13)	0.0261 (13)	0.0099 (12)	0.0100 (11)	0.0044 (11)
C9	0.0293 (14)	0.0337 (14)	0.0300 (14)	0.0100 (12)	0.0104 (11)	0.0061 (11)
C10	0.0374 (16)	0.0418 (16)	0.0289 (14)	0.0120 (13)	0.0103 (12)	0.0081 (12)
C11	0.0458 (17)	0.0408 (16)	0.0390 (16)	0.0125 (14)	0.0186 (14)	0.0153 (13)
C12	0.0347 (16)	0.0394 (16)	0.0427 (16)	0.0064 (13)	0.0168 (13)	0.0098 (13)
C13	0.0350 (16)	0.0464 (17)	0.0368 (16)	0.0057 (13)	0.0069 (13)	0.0127 (13)
C14	0.0335 (15)	0.0383 (15)	0.0322 (14)	0.0091 (12)	0.0115 (12)	0.0113 (12)
C15	0.0315 (15)	0.0325 (14)	0.0335 (15)	0.0059 (12)	0.0112 (12)	0.0082 (11)
C16	0.0364 (16)	0.0400 (15)	0.0310 (15)	0.0084 (13)	0.0064 (12)	0.0105 (12)
C17	0.0424 (16)	0.0368 (15)	0.0338 (15)	0.0152 (13)	0.0146 (13)	0.0120 (12)
C18	0.0407 (17)	0.0352 (15)	0.0400 (16)	0.0036 (13)	0.0120 (13)	0.0086 (12)
C19	0.0355 (16)	0.0391 (15)	0.0317 (15)	0.0033 (13)	0.0054 (12)	0.0057 (12)
C20	0.0335 (15)	0.0305 (14)	0.0292 (14)	0.0081 (12)	0.0089 (12)	0.0051 (11)
N1	0.0478 (17)	0.0555 (19)	0.0450 (15)	0.0277 (14)	0.0185 (13)	0.0150 (13)
N2	0.0363 (13)	0.0395 (13)	0.0299 (12)	0.0183 (11)	0.0110 (10)	0.0057 (10)
O1	0.0704 (15)	0.0539 (13)	0.0362 (12)	0.0245 (12)	0.0133 (10)	−0.0055 (10)
O2	0.0523 (14)	0.0523 (13)	0.0484 (13)	−0.0072 (11)	0.0124 (11)	0.0178 (11)
O3	0.0350 (11)	0.0515 (12)	0.0369 (11)	−0.0028 (9)	0.0006 (9)	0.0206 (9)
O4	0.0568 (14)	0.0488 (13)	0.0396 (12)	0.0090 (10)	0.0116 (10)	0.0214 (10)
O1W	0.0552 (14)	0.0654 (14)	0.0384 (12)	0.0146 (12)	0.0160 (11)	0.0133 (11)

C1—O1	1.229 (3)	C12—O2	1.362 (3)
C1—N2	1.356 (3)	C12—C13	1.375 (4)
C1—C2	1.477 (4)	C13—C14	1.384 (4)
C2—C3	1.381 (4)	C13—H13	0.9300
C2—C7	1.388 (4)	C14—O3	1.380 (3)
C3—C4	1.385 (4)	C15—O3	1.377 (3)
C3—H3	0.9300	C15—C16	1.382 (4)
C4—C5	1.391 (4)	C15—C20	1.394 (4)
C4—H4	0.9300	C16—C17	1.381 (4)
C5—C6	1.393 (4)	C16—H16	0.9300
C5—H5	0.9300	C17—O4	1.362 (3)
C6—C7	1.371 (4)	C17—C18	1.396 (4)
C6—H6	0.9300	C18—C19	1.373 (4)
C7—C8	1.523 (4)	C18—H18	0.9300
C8—N2	1.497 (3)	C19—C20	1.389 (4)
C8—C20	1.511 (4)	C19—H19	0.9300
C8—C9	1.513 (4)	N1—N2	1.396 (3)
C9—C14	1.384 (4)	N1—H1A	0.81 (4)
C9—C10	1.400 (4)	N1—H1B	0.89 (3)
C10—C11	1.373 (4)	O2—H2	0.8200
C10—H10	0.9300	O4—H4A	0.8200
C11—C12	1.391 (4)	O1W—H1WA	0.8473
C11—H11	0.9300	O1W—H1WB	0.8723
O1—C1—N2	124.0 (3)	O2—C12—C11	117.6 (3)
O1—C1—C2	130.1 (3)	C13—C12—C11	119.4 (3)
N2—C1—C2	105.9 (2)	C12—C13—C14	119.8 (3)
C3—C2—C7	121.4 (3)	C12—C13—H13	120.1
C3—C2—C1	129.7 (3)	C14—C13—H13	120.1
C7—C2—C1	108.8 (2)	O3—C14—C9	122.5 (2)
C2—C3—C4	118.0 (3)	O3—C14—C13	115.0 (2)
C2—C3—H3	121.0	C9—C14—C13	122.4 (3)
C4—C3—H3	121.0	O3—C15—C16	115.0 (2)
C3—C4—C5	120.5 (3)	O3—C15—C20	122.6 (2)
C3—C4—H4	119.8	C16—C15—C20	122.3 (3)
C5—C4—H4	119.8	C17—C16—C15	119.2 (2)
C4—C5—C6	121.2 (3)	C17—C16—H16	120.4
C4—C5—H5	119.4	C15—C16—H16	120.4
C6—C5—H5	119.4	O4—C17—C16	117.5 (2)
C7—C6—C5	117.9 (3)	O4—C17—C18	122.6 (3)
C7—C6—H6	121.0	C16—C17—C18	119.9 (3)
C5—C6—H6	121.0	C19—C18—C17	119.7 (3)
C6—C7—C2	121.0 (2)	C19—C18—H18	120.2
C6—C7—C8	128.1 (2)	C17—C18—H18	120.2
C2—C7—C8	110.9 (2)	C18—C19—C20	122.0 (2)
N2—C8—C20	109.8 (2)	C18—C19—H19	119.0
N2—C8—C9	109.7 (2)	C20—C19—H19	119.0
C20—C8—C9	110.8 (2)	C19—C20—C15	117.0 (2)
N2—C8—C7	99.09 (19)	C19—C20—C8	121.8 (2)
C20—C8—C7	113.7 (2)	C15—C20—C8	121.0 (2)
C9—C8—C7	113.1 (2)	N2—N1—H1A	108 (3)
C14—C9—C10	116.4 (2)	N2—N1—H1B	108.0 (14)
C14—C9—C8	121.5 (2)	H1A—N1—H1B	110 (3)
C10—C9—C8	122.1 (2)	C1—N2—N1	124.5 (2)
C11—C10—C9	122.1 (2)	C1—N2—C8	115.0 (2)
C11—C10—H10	118.9	N1—N2—C8	119.5 (2)
C9—C10—H10	118.9	C12—O2—H2	109.5
C10—C11—C12	119.8 (3)	C15—O3—C14	118.9 (2)
C10—C11—H11	120.1	C17—O4—H4A	109.5
C12—C11—H11	120.1	H1WA—O1W—H1WB	112.6
O2—C12—C13	123.0 (3)
O1—C1—C2—C3	4.5 (5)	C8—C9—C14—C13	−177.9 (2)
N2—C1—C2—C3	−176.3 (3)	C12—C13—C14—O3	179.6 (3)
O1—C1—C2—C7	−175.8 (3)	C12—C13—C14—C9	−0.2 (4)
N2—C1—C2—C7	3.3 (3)	O3—C15—C16—C17	−179.8 (2)
C7—C2—C3—C4	0.6 (5)	C20—C15—C16—C17	−0.2 (4)
C1—C2—C3—C4	−179.8 (3)	C15—C16—C17—O4	179.6 (2)
C2—C3—C4—C5	−0.2 (5)	C15—C16—C17—C18	−0.1 (4)
C3—C4—C5—C6	0.1 (5)	O4—C17—C18—C19	−179.3 (3)
C4—C5—C6—C7	−0.6 (5)	C16—C17—C18—C19	0.4 (4)
C5—C6—C7—C2	1.0 (4)	C17—C18—C19—C20	−0.5 (4)
C5—C6—C7—C8	−178.8 (3)	C18—C19—C20—C15	0.2 (4)
C3—C2—C7—C6	−1.1 (4)	C18—C19—C20—C8	−174.9 (3)
C1—C2—C7—C6	179.2 (3)	O3—C15—C20—C19	179.7 (2)
C3—C2—C7—C8	178.8 (3)	C16—C15—C20—C19	0.1 (4)
C1—C2—C7—C8	−0.9 (3)	O3—C15—C20—C8	−5.2 (4)
C6—C7—C8—N2	178.2 (3)	C16—C15—C20—C8	175.3 (2)
C2—C7—C8—N2	−1.7 (3)	N2—C8—C20—C19	69.3 (3)
C6—C7—C8—C20	−65.4 (4)	C9—C8—C20—C19	−169.3 (2)
C2—C7—C8—C20	114.7 (3)	C7—C8—C20—C19	−40.6 (3)
C6—C7—C8—C9	62.1 (4)	N2—C8—C20—C15	−105.5 (3)
C2—C7—C8—C9	−117.8 (2)	C9—C8—C20—C15	15.8 (3)
N2—C8—C9—C14	106.9 (3)	C7—C8—C20—C15	144.5 (2)
C20—C8—C9—C14	−14.5 (3)	O1—C1—N2—N1	5.6 (5)
C7—C8—C9—C14	−143.5 (3)	C2—C1—N2—N1	−173.6 (3)
N2—C8—C9—C10	−70.9 (3)	O1—C1—N2—C8	174.5 (3)
C20—C8—C9—C10	167.7 (2)	C2—C1—N2—C8	−4.7 (3)
C7—C8—C9—C10	38.7 (3)	C20—C8—N2—C1	−115.3 (3)
C14—C9—C10—C11	0.0 (4)	C9—C8—N2—C1	122.7 (2)
C8—C9—C10—C11	178.0 (2)	C7—C8—N2—C1	4.0 (3)
C9—C10—C11—C12	0.1 (4)	C20—C8—N2—N1	54.2 (3)
C10—C11—C12—O2	178.5 (3)	C9—C8—N2—N1	−67.8 (3)
C10—C11—C12—C13	−0.2 (4)	C7—C8—N2—N1	173.5 (3)
O2—C12—C13—C14	−178.3 (3)	C16—C15—O3—C14	170.9 (2)
C11—C12—C13—C14	0.3 (4)	C20—C15—O3—C14	−8.7 (4)
C10—C9—C14—O3	−179.7 (2)	C9—C14—O3—C15	10.1 (4)
C8—C9—C14—O3	2.3 (4)	C13—C14—O3—C15	−169.6 (2)
C10—C9—C14—C13	0.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O1Wi	0.82	1.99	2.790 (3)	165
N1—H1B···O1ii	0.89 (3)	2.534 (16)	3.025 (3)	115.4 (19)
O2—H2···O1Wiii	0.82	1.95	2.760 (3)	170
O1W—H1WA···N1	0.85	2.23	2.883 (3)	134
O1W—H1WB···O1ii	0.87	2.06	2.861 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O1Wi	0.82	1.99	2.790 (3)	165
N1—H1B⋯O1ii	0.89 (3)	2.534 (16)	3.025 (3)	115.4 (19)
O2—H2⋯O1Wiii	0.82	1.95	2.760 (3)	170
O1W—H1WA⋯N1	0.85	2.23	2.883 (3)	134
O1W—H1WB⋯O1ii	0.87	2.06	2.861 (3)	152

Symmetry codes: (i) ; (ii) ; (iii) .