3-[(2-Hydr­oxy-5-nitro­phen­yl)amino]-2-benzofuran-1(3H)-one monohydrate

The crystal structure of the title compound, C₁₄H₁₀N₂O₅·H₂O, is stabilized by inversion-related O—H...O and C—H...O inter­molecular hydrogen bonds and also by π–π inter­actions. The dihedral angle between the phthalide group and the benzene ring is 51.45 (8)°.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.042
• wR factor = 0.115
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H6B    ..  H6B     ..       1.89 Ang.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT731_ALERT_1_C Bond    Calc     0.79(4), Rep   0.790(19) ......       2.11 su-Rat
              O6   -H6A     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.79(5), Rep   0.794(19) ......       2.63 su-Rat
              O6   -H6B     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.79(4), Rep   0.790(19) ......       2.11 su-Rat
              O6   -H6A     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.79(4), Rep   0.790(19) ......       2.11 su-Rat
              O6   -H6A     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.79(5), Rep   0.794(19) ......       2.63 su-Rat
              O6   -H6B     1.555   1.555

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-[(2-Hydroxy-5-nitrophenyl)amino]-2-benzofuran-1(3H)-one monohydrate

Crystal data

C14H10N2O5·H2O	F(000) = 632
Mr = 304.26	Dx = 1.508 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 18837 reflections
a = 10.8202 (7) Å	θ = 2.3–28.0°
b = 9.8139 (4) Å	µ = 0.12 mm^−1
c = 15.1475 (10) Å	T = 296 K
β = 123.588 (4)°	Prism, light brown
V = 1339.93 (14) Å^3	0.45 × 0.34 × 0.14 mm
Z = 4

Data collection

Stoe IPDS-II diffractometer	2628 independent reflections
Radiation source: fine-focus sealed tube	2077 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.090
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 2.3°
ω scans	h = −13→13
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→12
Tmin = 0.952, Tmax = 0.984	l = −18→18
18837 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0646P)^2 + 0.1854P] where P = (Fo^2 + 2Fc^2)/3
2628 reflections	(Δ/σ)max < 0.001
207 parameters	Δρmax = 0.24 e Å^−3
3 restraints	Δρmin = −0.22 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.60464 (19)	0.14962 (16)	0.19227 (12)	0.0443 (4)
C2	0.49812 (17)	0.23027 (15)	0.09903 (12)	0.0402 (3)
C3	0.43360 (19)	0.20241 (17)	−0.00746 (12)	0.0478 (4)
H3	0.4531	0.1216	−0.0297	0.057*
C4	0.3393 (2)	0.29940 (18)	−0.07913 (13)	0.0532 (4)
H4	0.2936	0.2839	−0.1513	0.064*
C5	0.31169 (19)	0.41983 (18)	−0.04505 (13)	0.0546 (4)
H5	0.2481	0.4839	−0.0950	0.065*
C6	0.37636 (19)	0.44694 (17)	0.06122 (13)	0.0490 (4)
H6	0.3576	0.5279	0.0837	0.059*
C7	0.46990 (17)	0.34939 (15)	0.13290 (12)	0.0405 (3)
C8	0.55973 (18)	0.35106 (15)	0.25181 (12)	0.0427 (4)
H8	0.4935	0.3507	0.2770	0.051*
C9	0.74754 (16)	0.49136 (15)	0.40150 (11)	0.0397 (3)
C10	0.82439 (17)	0.61583 (15)	0.43100 (12)	0.0410 (3)
C11	0.91826 (18)	0.64999 (16)	0.53655 (12)	0.0455 (4)
H11	0.9681	0.7329	0.5552	0.055*
C12	0.93865 (18)	0.56193 (16)	0.61459 (12)	0.0455 (4)
H12	1.0014	0.5846	0.6859	0.055*
C13	0.86401 (17)	0.44001 (15)	0.58446 (12)	0.0410 (4)
C14	0.76820 (17)	0.40241 (16)	0.47896 (12)	0.0415 (3)
H14	0.7191	0.3191	0.4610	0.050*
N1	0.65444 (16)	0.46414 (14)	0.29330 (10)	0.0477 (3)
H1	0.6552	0.5197	0.2497	0.057*
N2	0.88986 (16)	0.34320 (14)	0.66530 (11)	0.0489 (3)
O1	0.65643 (15)	0.03851 (12)	0.19793 (10)	0.0578 (3)
O2	0.64292 (13)	0.22039 (11)	0.28037 (8)	0.0493 (3)
O3	0.79939 (14)	0.69517 (11)	0.34976 (9)	0.0527 (3)
H3A	0.8479	0.7656	0.3732	0.079*
O4	0.97407 (16)	0.37473 (15)	0.75877 (9)	0.0655 (4)
O5	0.82640 (18)	0.23300 (14)	0.63813 (10)	0.0726 (4)
O6	0.9234 (3)	−0.06097 (17)	0.39383 (16)	0.0860 (5)
H6A	0.893 (5)	−0.008 (4)	0.347 (3)	0.21 (2)*
H6B	0.999 (4)	−0.028 (5)	0.440 (3)	0.23 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0518 (9)	0.0381 (8)	0.0382 (8)	−0.0026 (7)	0.0218 (7)	−0.0011 (6)
C2	0.0430 (8)	0.0375 (7)	0.0347 (7)	−0.0046 (6)	0.0181 (7)	−0.0036 (6)
C3	0.0560 (10)	0.0456 (9)	0.0374 (8)	−0.0074 (7)	0.0231 (7)	−0.0091 (7)
C4	0.0565 (10)	0.0585 (10)	0.0311 (8)	−0.0084 (8)	0.0158 (7)	−0.0031 (7)
C5	0.0509 (10)	0.0502 (10)	0.0404 (9)	0.0005 (8)	0.0113 (8)	0.0045 (7)
C6	0.0487 (9)	0.0405 (8)	0.0436 (9)	0.0018 (7)	0.0165 (7)	−0.0028 (7)
C7	0.0415 (8)	0.0383 (8)	0.0335 (7)	−0.0055 (6)	0.0158 (6)	−0.0052 (6)
C8	0.0476 (9)	0.0382 (8)	0.0343 (7)	−0.0022 (6)	0.0177 (7)	−0.0038 (6)
C9	0.0403 (8)	0.0384 (8)	0.0316 (7)	0.0003 (6)	0.0144 (6)	−0.0043 (6)
C10	0.0451 (8)	0.0364 (7)	0.0382 (8)	0.0013 (6)	0.0210 (7)	−0.0019 (6)
C11	0.0485 (9)	0.0386 (8)	0.0414 (8)	−0.0050 (6)	0.0198 (7)	−0.0083 (6)
C12	0.0445 (8)	0.0462 (9)	0.0332 (7)	0.0002 (7)	0.0137 (7)	−0.0062 (6)
C13	0.0413 (8)	0.0420 (8)	0.0326 (7)	0.0051 (6)	0.0159 (6)	0.0005 (6)
C14	0.0440 (8)	0.0363 (7)	0.0369 (8)	−0.0014 (6)	0.0177 (7)	−0.0040 (6)
N1	0.0588 (8)	0.0418 (7)	0.0296 (6)	−0.0096 (6)	0.0163 (6)	−0.0039 (5)
N2	0.0512 (8)	0.0475 (8)	0.0378 (7)	0.0047 (6)	0.0182 (6)	0.0022 (6)
O1	0.0705 (8)	0.0415 (6)	0.0530 (7)	0.0096 (6)	0.0288 (6)	0.0024 (5)
O2	0.0612 (7)	0.0402 (6)	0.0325 (5)	0.0020 (5)	0.0171 (5)	0.0000 (4)
O3	0.0674 (8)	0.0414 (6)	0.0400 (6)	−0.0081 (5)	0.0238 (6)	−0.0007 (5)
O4	0.0687 (9)	0.0713 (8)	0.0320 (6)	0.0003 (6)	0.0125 (6)	0.0047 (5)
O5	0.0933 (11)	0.0501 (8)	0.0512 (7)	−0.0128 (7)	0.0255 (7)	0.0056 (6)
O6	0.1111 (14)	0.0619 (9)	0.0708 (10)	−0.0229 (9)	0.0414 (10)	0.0007 (8)

Geometric parameters (Å, º)

C1—O1	1.207 (2)	C9—N1	1.3949 (19)
C1—O2	1.3502 (19)	C9—C10	1.404 (2)
C1—C2	1.466 (2)	C10—O3	1.3510 (19)
C2—C7	1.377 (2)	C10—C11	1.380 (2)
C2—C3	1.385 (2)	C11—C12	1.380 (2)
C3—C4	1.378 (2)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.373 (2)
C4—C5	1.387 (3)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.390 (2)
C5—C6	1.380 (2)	C13—N2	1.450 (2)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.380 (2)	N1—H1	0.8600
C6—H6	0.9300	N2—O5	1.2239 (19)
C7—C8	1.501 (2)	N2—O4	1.2259 (18)
C8—N1	1.401 (2)	O3—H3A	0.8200
C8—O2	1.4869 (19)	O6—H6A	0.790 (19)
C8—H8	0.9800	O6—H6B	0.794 (19)
C9—C14	1.378 (2)
O1—C1—O2	121.19 (14)	C14—C9—N1	123.41 (14)
O1—C1—C2	130.00 (15)	C14—C9—C10	119.45 (13)
O2—C1—C2	108.80 (13)	N1—C9—C10	117.13 (14)
C7—C2—C3	121.92 (15)	O3—C10—C11	124.30 (14)
C7—C2—C1	108.52 (13)	O3—C10—C9	115.25 (13)
C3—C2—C1	129.55 (15)	C11—C10—C9	120.45 (14)
C4—C3—C2	117.23 (15)	C10—C11—C12	120.46 (15)
C4—C3—H3	121.4	C10—C11—H11	119.8
C2—C3—H3	121.4	C12—C11—H11	119.8
C3—C4—C5	120.89 (15)	C13—C12—C11	118.37 (14)
C3—C4—H4	119.6	C13—C12—H12	120.8
C5—C4—H4	119.6	C11—C12—H12	120.8
C6—C5—C4	121.58 (16)	C12—C13—C14	122.76 (14)
C6—C5—H5	119.2	C12—C13—N2	119.16 (13)
C4—C5—H5	119.2	C14—C13—N2	118.03 (14)
C7—C6—C5	117.50 (15)	C9—C14—C13	118.51 (14)
C7—C6—H6	121.2	C9—C14—H14	120.7
C5—C6—H6	121.2	C13—C14—H14	120.7
C2—C7—C6	120.87 (15)	C9—N1—C8	123.51 (13)
C2—C7—C8	109.06 (13)	C9—N1—H1	118.2
C6—C7—C8	130.01 (14)	C8—N1—H1	118.2
N1—C8—O2	112.19 (13)	O5—N2—O4	122.12 (15)
N1—C8—C7	111.98 (13)	O5—N2—C13	119.00 (13)
O2—C8—C7	103.04 (11)	O4—N2—C13	118.87 (14)
N1—C8—H8	109.8	C1—O2—C8	110.54 (11)
O2—C8—H8	109.8	C10—O3—H3A	109.5
C7—C8—H8	109.8	H6A—O6—H6B	104 (3)
O1—C1—C2—C7	178.46 (18)	N1—C9—C10—C11	179.86 (15)
O2—C1—C2—C7	−1.69 (18)	O3—C10—C11—C12	−179.22 (15)
O1—C1—C2—C3	−3.1 (3)	C9—C10—C11—C12	0.4 (2)
O2—C1—C2—C3	176.72 (16)	C10—C11—C12—C13	0.3 (2)
C7—C2—C3—C4	0.1 (2)	C11—C12—C13—C14	−0.6 (2)
C1—C2—C3—C4	−178.09 (16)	C11—C12—C13—N2	176.84 (15)
C2—C3—C4—C5	0.3 (3)	N1—C9—C14—C13	179.85 (14)
C3—C4—C5—C6	−0.4 (3)	C10—C9—C14—C13	0.7 (2)
C4—C5—C6—C7	−0.1 (3)	C12—C13—C14—C9	0.1 (2)
C3—C2—C7—C6	−0.6 (2)	N2—C13—C14—C9	−177.38 (14)
C1—C2—C7—C6	177.95 (15)	C14—C9—N1—C8	7.5 (3)
C3—C2—C7—C8	−178.12 (14)	C10—C9—N1—C8	−173.36 (15)
C1—C2—C7—C8	0.43 (18)	O2—C8—N1—C9	−66.11 (19)
C5—C6—C7—C2	0.6 (3)	C7—C8—N1—C9	178.59 (14)
C5—C6—C7—C8	177.51 (16)	C12—C13—N2—O5	−177.91 (16)
C2—C7—C8—N1	121.60 (15)	C14—C13—N2—O5	−0.4 (2)
C6—C7—C8—N1	−55.6 (2)	C12—C13—N2—O4	2.5 (2)
C2—C7—C8—O2	0.83 (16)	C14—C13—N2—O4	179.99 (15)
C6—C7—C8—O2	−176.38 (16)	O1—C1—O2—C8	−177.88 (15)
C14—C9—C10—O3	178.74 (14)	C2—C1—O2—C8	2.26 (18)
N1—C9—C10—O3	−0.5 (2)	N1—C8—O2—C1	−122.54 (14)
C14—C9—C10—C11	−0.9 (2)	C7—C8—O2—C1	−1.92 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O6^i	0.82	1.84	2.643 (2)	166
O6—H6A···O1	0.79 (2)	2.34 (4)	2.936 (3)	133 (4)
O6—H6A···O4^ii	0.79 (2)	2.36 (4)	3.011 (2)	141 (5)
O6—H6B···O6^iii	0.79 (2)	2.34 (4)	2.937 (4)	133 (5)
C4—H4···O3^iv	0.93	2.60	3.500 (2)	164
C5—H5···O5^v	0.93	2.54	3.367 (2)	148

Symmetry codes: (i) x, y+1, z; (ii) x, −y+1/2, z−1/2; (iii) −x+2, −y, −z+1; (iv) −x+1, −y+1, −z; (v) −x+1, y+1/2, −z+1/2.