4-(2-Meth­oxy-4-nitro­phenyl­diazen­yl)phenol monohydrate

The organic molecule of the title compound, C₁₃H₁₁N₃O₄·H₂O, is essentially planar. The two benzene rings make a dihedral angle of only 1.6 (1)° and the nitro group is rotated only 3.6 (1)° from the plane of its attached benzene ring. In the crystal structure, the planar mol­ecules stack along [100] through π–π inter­actions, and these stacks inter­act laterally through strong and weak hydrogen bonds. The solvent water mol­ecule is involved in all of the strong inter­actions through O—H...O(water), N...H—O(water) and O...H—O(water) hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.055
• wR factor = 0.131
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8     ..  O5      ..       2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10    ..  O4      ..       2.71 Ang.

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

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

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Computing details

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003); 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: SHELXTL (Sheldrick, 1997).

4-(2-Methoxy-4-nitrophenyldiazenyl)phenol monohydrate

Crystal data

C13H11N3O4·H2O	Z = 2
Mr = 291.26	F(000) = 304
Triclinic, P1	Dx = 1.445 Mg m^−3
Hall symbol: -P 1	Melting point: 499 K
a = 7.2392 (18) Å	Mo Kα radiation, λ = 0.71070 Å
b = 8.6741 (15) Å	Cell parameters from 2640 reflections
c = 11.066 (3) Å	θ = 3.4–27.5°
α = 75.286 (11)°	µ = 0.11 mm^−1
β = 88.505 (15)°	T = 193 K
γ = 84.737 (15)°	Chip, orange
V = 669.3 (3) Å^3	0.40 × 0.35 × 0.17 mm

Data collection

Rigaku Mercury diffractometer	2996 independent reflections
Radiation source: fine-focus sealed tube	2568 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 7.31 pixels mm^-1	θmax = 27.5°, θmin = 3.4°
ω scans	h = −9→9
Absorption correction: multi-scan (Jacobson, 1998)	k = −11→11
Tmin = 0.956, Tmax = 0.981	l = −14→11
7473 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ^2(Fo^2) + (0.0575P)^2 + 0.1914P] where P = (Fo^2 + 2Fc^2)/3
2996 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.26 e Å^−3
0 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
O1	0.05712 (18)	−0.62942 (13)	0.85645 (10)	0.0346 (3)
H1	0.0433	−0.6909	0.8103	0.052*
O2	0.27545 (16)	0.06065 (12)	0.22128 (10)	0.0299 (3)
O3	0.4557 (2)	0.70362 (14)	0.24945 (13)	0.0500 (4)
O4	0.4171 (2)	0.63411 (15)	0.07898 (11)	0.0444 (3)
O5	0.9941 (2)	0.17111 (15)	0.71625 (12)	0.0381 (3)
H5A	1.078 (4)	0.122 (4)	0.678 (3)	0.086 (9)*
H5B	0.902 (4)	0.121 (3)	0.720 (2)	0.072 (8)*
N1	0.25982 (16)	−0.00952 (14)	0.46748 (11)	0.0240 (3)
N2	0.23014 (17)	−0.02976 (15)	0.58330 (11)	0.0242 (3)
N3	0.41916 (19)	0.60607 (15)	0.19300 (13)	0.0299 (3)
C1	0.3328 (2)	0.26703 (18)	0.46383 (14)	0.0255 (3)
H1A	0.3310	0.2437	0.5525	0.031*
C2	0.3694 (2)	0.41758 (18)	0.39486 (14)	0.0259 (3)
H2	0.3895	0.4994	0.4349	0.031*
C3	0.3761 (2)	0.44652 (17)	0.26627 (14)	0.0235 (3)
C4	0.3471 (2)	0.33273 (17)	0.20297 (14)	0.0239 (3)
H4A	0.3542	0.3567	0.1144	0.029*
C5	0.30725 (19)	0.18181 (17)	0.27285 (14)	0.0225 (3)
C6	0.29842 (19)	0.14870 (17)	0.40423 (13)	0.0218 (3)
C7	0.1615 (2)	−0.30650 (17)	0.58683 (13)	0.0248 (3)
H7	0.1713	−0.2853	0.4985	0.030*
C8	0.1175 (2)	−0.45451 (17)	0.65558 (14)	0.0250 (3)
H8	0.0960	−0.5349	0.6145	0.030*
C9	0.1046 (2)	−0.48669 (17)	0.78558 (13)	0.0235 (3)
C10	0.1378 (2)	−0.36974 (19)	0.84615 (14)	0.0276 (3)
H10	0.1315	−0.3921	0.9347	0.033*
C11	0.1801 (2)	−0.22087 (18)	0.77670 (14)	0.0264 (3)
H11	0.2015	−0.1405	0.8178	0.032*
C12	0.19181 (19)	−0.18742 (17)	0.64657 (13)	0.0224 (3)
C13	0.2944 (3)	0.0876 (2)	0.08859 (15)	0.0427 (5)
H13A	0.2027	0.1739	0.0473	0.064*
H13B	0.2740	−0.0106	0.0643	0.064*
H13C	0.4195	0.1179	0.0634	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0537 (7)	0.0247 (6)	0.0234 (6)	−0.0112 (5)	0.0057 (5)	0.0000 (4)
O2	0.0487 (7)	0.0210 (5)	0.0213 (5)	−0.0100 (5)	0.0067 (5)	−0.0059 (4)
O3	0.0811 (10)	0.0240 (6)	0.0478 (8)	−0.0180 (6)	0.0006 (7)	−0.0100 (5)
O4	0.0679 (9)	0.0331 (7)	0.0295 (7)	−0.0197 (6)	0.0039 (6)	0.0019 (5)
O5	0.0478 (8)	0.0306 (6)	0.0396 (7)	−0.0145 (6)	0.0096 (6)	−0.0128 (5)
N1	0.0252 (6)	0.0219 (6)	0.0224 (6)	−0.0037 (5)	0.0023 (5)	−0.0010 (5)
N2	0.0250 (6)	0.0249 (6)	0.0215 (6)	−0.0048 (5)	0.0013 (5)	−0.0025 (5)
N3	0.0321 (7)	0.0211 (6)	0.0350 (8)	−0.0058 (5)	0.0012 (6)	−0.0034 (5)
C1	0.0275 (7)	0.0295 (8)	0.0195 (7)	−0.0073 (6)	0.0002 (6)	−0.0046 (6)
C2	0.0260 (7)	0.0248 (7)	0.0286 (8)	−0.0068 (6)	−0.0002 (6)	−0.0083 (6)
C3	0.0209 (7)	0.0188 (7)	0.0291 (8)	−0.0032 (5)	0.0019 (6)	−0.0026 (6)
C4	0.0268 (7)	0.0220 (7)	0.0216 (7)	−0.0038 (6)	0.0028 (6)	−0.0025 (6)
C5	0.0223 (7)	0.0205 (7)	0.0248 (7)	−0.0027 (5)	0.0026 (6)	−0.0059 (6)
C6	0.0193 (7)	0.0203 (7)	0.0238 (7)	−0.0020 (5)	0.0017 (5)	−0.0017 (5)
C7	0.0306 (8)	0.0249 (7)	0.0171 (7)	−0.0019 (6)	0.0018 (6)	−0.0027 (5)
C8	0.0296 (8)	0.0223 (7)	0.0227 (7)	−0.0031 (6)	0.0019 (6)	−0.0047 (6)
C9	0.0249 (7)	0.0205 (7)	0.0217 (7)	−0.0024 (5)	0.0023 (6)	0.0008 (5)
C10	0.0337 (8)	0.0308 (8)	0.0169 (7)	−0.0054 (6)	0.0012 (6)	−0.0028 (6)
C11	0.0324 (8)	0.0259 (7)	0.0212 (7)	−0.0053 (6)	−0.0008 (6)	−0.0058 (6)
C12	0.0206 (7)	0.0227 (7)	0.0219 (7)	−0.0026 (5)	0.0014 (5)	−0.0019 (5)
C13	0.0775 (14)	0.0306 (9)	0.0231 (8)	−0.0163 (9)	0.0118 (8)	−0.0095 (7)

Geometric parameters (Å, º)

O1—C9	1.3551 (17)	C3—C4	1.381 (2)
O1—H1	0.8400	C4—C5	1.392 (2)
O2—C5	1.3561 (17)	C4—H4A	0.9500
O2—C13	1.4320 (19)	C5—C6	1.409 (2)
O3—N3	1.2224 (18)	C7—C8	1.376 (2)
O4—N3	1.2230 (18)	C7—C12	1.396 (2)
O5—H5A	0.87 (3)	C7—H7	0.9500
O5—H5B	0.83 (3)	C8—C9	1.396 (2)
N1—N2	1.2641 (17)	C8—H8	0.9500
N1—C6	1.4226 (18)	C9—C10	1.391 (2)
N2—C12	1.4179 (18)	C10—C11	1.381 (2)
N3—C3	1.4716 (19)	C10—H10	0.9500
C1—C2	1.380 (2)	C11—C12	1.397 (2)
C1—C6	1.396 (2)	C11—H11	0.9500
C1—H1A	0.9500	C13—H13A	0.9800
C2—C3	1.381 (2)	C13—H13B	0.9800
C2—H2	0.9500	C13—H13C	0.9800
C9—O1—H1	109.5	C5—C6—N1	115.89 (13)
C5—O2—C13	117.86 (12)	C8—C7—C12	120.20 (13)
H5A—O5—H5B	105 (3)	C8—C7—H7	119.9
N2—N1—C6	114.24 (12)	C12—C7—H7	119.9
N1—N2—C12	114.35 (12)	C7—C8—C9	120.13 (14)
O3—N3—O4	123.41 (14)	C7—C8—H8	119.9
O3—N3—C3	118.18 (14)	C9—C8—H8	119.9
O4—N3—C3	118.42 (13)	O1—C9—C10	117.90 (13)
C2—C1—C6	120.47 (14)	O1—C9—C8	122.00 (14)
C2—C1—H1A	119.8	C10—C9—C8	120.09 (13)
C6—C1—H1A	119.8	C11—C10—C9	119.56 (14)
C1—C2—C3	118.42 (14)	C11—C10—H10	120.2
C1—C2—H2	120.8	C9—C10—H10	120.2
C3—C2—H2	120.8	C10—C11—C12	120.64 (14)
C4—C3—C2	123.36 (13)	C10—C11—H11	119.7
C4—C3—N3	118.28 (13)	C12—C11—H11	119.7
C2—C3—N3	118.35 (13)	C7—C12—C11	119.36 (13)
C3—C4—C5	118.00 (14)	C7—C12—N2	124.16 (13)
C3—C4—H4A	121.0	C11—C12—N2	116.47 (13)
C5—C4—H4A	121.0	O2—C13—H13A	109.5
O2—C5—C4	123.40 (13)	O2—C13—H13B	109.5
O2—C5—C6	116.57 (12)	H13A—C13—H13B	109.5
C4—C5—C6	120.02 (13)	O2—C13—H13C	109.5
C1—C6—C5	119.69 (13)	H13A—C13—H13C	109.5
C1—C6—N1	124.39 (13)	H13B—C13—H13C	109.5
C6—N1—N2—C12	−179.94 (11)	C4—C5—C6—C1	−1.0 (2)
C6—C1—C2—C3	−1.8 (2)	O2—C5—C6—N1	0.94 (19)
C1—C2—C3—C4	0.3 (2)	C4—C5—C6—N1	−179.01 (12)
C1—C2—C3—N3	−178.70 (13)	N2—N1—C6—C1	10.5 (2)
O3—N3—C3—C4	−175.72 (14)	N2—N1—C6—C5	−171.68 (12)
O4—N3—C3—C4	4.1 (2)	C12—C7—C8—C9	−0.6 (2)
O3—N3—C3—C2	3.4 (2)	C7—C8—C9—O1	178.33 (14)
O4—N3—C3—C2	−176.82 (14)	C7—C8—C9—C10	−0.6 (2)
C2—C3—C4—C5	0.7 (2)	O1—C9—C10—C11	−177.73 (13)
N3—C3—C4—C5	179.74 (12)	C8—C9—C10—C11	1.3 (2)
C13—O2—C5—C4	3.6 (2)	C9—C10—C11—C12	−0.7 (2)
C13—O2—C5—C6	−176.33 (14)	C8—C7—C12—C11	1.1 (2)
C3—C4—C5—O2	179.73 (13)	C8—C7—C12—N2	−177.29 (13)
C3—C4—C5—C6	−0.3 (2)	C10—C11—C12—C7	−0.4 (2)
C2—C1—C6—C5	2.1 (2)	C10—C11—C12—N2	178.06 (13)
C2—C1—C6—N1	179.89 (13)	N1—N2—C12—C7	−9.0 (2)
O2—C5—C6—C1	178.90 (13)	N1—N2—C12—C11	172.55 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···O2^i	0.83 (3)	2.09 (3)	2.8757 (18)	160 (3)
O5—H5A···N2^ii	0.87 (3)	2.11 (3)	2.9572 (19)	166 (3)
O1—H1···O5^iii	0.84	1.84	2.6747 (18)	175
C8—H8···O5^iii	0.95	2.68	3.346 (2)	128
C10—H10···O4^iv	0.95	2.71	3.323 (2)	124
C13—H13A···O1^v	0.98	2.54	3.439 (2)	153

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