2-(2,4-Di­nitro­phen­yl)-1-(pyridin-4-yl)ethanol monohydrate

In the title compound, C₁₃H₁₁N₃O₅·H₂O, the dihedral angle between the aromatic rings is 9.60 (7)° and the chain linking the rings has an anti conformation with a torsion angle of −178.28 (12)°. In the crystal, the components are linked by O—H...O and O—H...N hydrogen bonds, generating (010) sheets.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.125
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         N8 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         N9 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.452 Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT793_ALERT_4_G Model has Chirality at C11         (Centro SPGR)          S Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        212 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (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: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2015).

2-(2,4-Dinitrophenyl)-1-(pyridin-4-yl)ethanol monohydrate

Crystal data

C13H11N3O5·H2O	F(000) = 640
Mr = 307.26	Dx = 1.481 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.639 (8) Å	Cell parameters from 6924 reflections
b = 20.045 (12) Å	θ = 2.6–27.1°
c = 8.116 (5) Å	µ = 0.12 mm^−1
β = 101.326 (5)°	T = 296 K
V = 1378.2 (17) Å^3	Block, yellow
Z = 4	0.19 × 0.18 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer	2531 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.025
ω scans	θmax = 27.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
Tmin = 0.616, Tmax = 0.746	k = −22→25
10488 measured reflections	l = −10→10
2889 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0605P)^2 + 0.4306P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
2889 reflections	Δρmax = 0.37 e Å^−3
208 parameters	Δρmin = −0.24 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O2	0.11854 (12)	0.30340 (6)	0.04733 (14)	0.0475 (3)
H2	0.0856	0.3009	−0.0544	0.071*
C3	−0.03252 (17)	0.51894 (7)	0.25550 (18)	0.0418 (3)
H3	−0.0432	0.5644	0.2332	0.050*
C4	0.10032 (16)	0.48431 (7)	0.23286 (18)	0.0389 (3)
C5	0.40549 (16)	0.30336 (7)	0.08026 (17)	0.0383 (3)
C6	0.12367 (17)	0.41637 (7)	0.26901 (17)	0.0393 (3)
C7	−0.14831 (17)	0.48357 (8)	0.31235 (18)	0.0435 (3)
N8	−0.29271 (16)	0.51917 (8)	0.33273 (18)	0.0563 (4)
N9	0.21854 (15)	0.52431 (6)	0.16714 (18)	0.0500 (3)
N10	0.68428 (15)	0.23063 (7)	0.09129 (19)	0.0534 (4)
C11	0.25687 (16)	0.34380 (7)	0.07980 (18)	0.0394 (3)
H11	0.2482	0.3787	−0.0060	0.047*
O12	0.30318 (16)	0.49757 (7)	0.08429 (19)	0.0669 (4)
C13	0.41333 (17)	0.23595 (7)	0.1180 (2)	0.0451 (3)
H13	0.3254	0.2137	0.1408	0.054*
O14	−0.30398 (18)	0.57810 (8)	0.2980 (2)	0.0795 (4)
C15	0.0034 (2)	0.38446 (8)	0.3309 (2)	0.0488 (4)
H15	0.0154	0.3396	0.3594	0.059*
C16	−0.1328 (2)	0.41660 (8)	0.3516 (2)	0.0504 (4)
H16	−0.2119	0.3937	0.3910	0.060*
C17	0.55312 (19)	0.20209 (8)	0.1213 (2)	0.0529 (4)
H17	0.5560	0.1567	0.1459	0.064*
C18	0.26799 (18)	0.37632 (7)	0.25304 (19)	0.0438 (3)
H18A	0.2839	0.3417	0.3382	0.053*
H18B	0.3596	0.4054	0.2747	0.053*
C19	0.54071 (18)	0.33341 (8)	0.0472 (2)	0.0499 (4)
H19	0.5407	0.3785	0.0205	0.060*
O20	0.2244 (2)	0.58322 (7)	0.1986 (3)	0.1047 (7)
C21	0.67505 (19)	0.29564 (9)	0.0543 (2)	0.0547 (4)
H21	0.7647	0.3166	0.0320	0.066*
O22	−0.3925 (2)	0.48738 (9)	0.3855 (3)	0.1002 (6)
O1	−0.00579 (15)	0.69790 (7)	0.28295 (16)	0.0537 (3)
H1A	−0.044 (3)	0.7282 (11)	0.324 (3)	0.072 (7)*
H1B	0.094 (3)	0.7007 (10)	0.319 (3)	0.072 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0343 (5)	0.0568 (6)	0.0508 (6)	−0.0054 (4)	0.0066 (4)	−0.0012 (5)
C3	0.0400 (7)	0.0391 (7)	0.0445 (7)	0.0017 (6)	0.0040 (6)	−0.0014 (6)
C4	0.0356 (7)	0.0387 (7)	0.0413 (7)	−0.0043 (5)	0.0053 (5)	−0.0016 (6)
C5	0.0340 (7)	0.0411 (7)	0.0395 (7)	−0.0008 (5)	0.0064 (5)	−0.0012 (5)
C6	0.0403 (7)	0.0395 (7)	0.0377 (7)	0.0010 (6)	0.0062 (5)	−0.0019 (5)
C7	0.0380 (7)	0.0513 (8)	0.0412 (7)	0.0024 (6)	0.0075 (6)	−0.0072 (6)
N8	0.0428 (7)	0.0717 (10)	0.0559 (8)	0.0063 (7)	0.0134 (6)	−0.0074 (7)
N9	0.0424 (7)	0.0421 (7)	0.0661 (9)	−0.0068 (5)	0.0121 (6)	−0.0001 (6)
N10	0.0366 (7)	0.0576 (8)	0.0659 (9)	0.0065 (6)	0.0094 (6)	0.0050 (7)
C11	0.0337 (7)	0.0408 (7)	0.0433 (7)	0.0001 (5)	0.0065 (5)	0.0032 (6)
O12	0.0645 (8)	0.0615 (8)	0.0841 (9)	−0.0096 (6)	0.0378 (7)	−0.0020 (7)
C13	0.0352 (7)	0.0427 (8)	0.0577 (9)	−0.0029 (6)	0.0095 (6)	0.0028 (6)
O14	0.0669 (9)	0.0698 (9)	0.1059 (12)	0.0257 (7)	0.0271 (8)	0.0022 (8)
C15	0.0599 (9)	0.0382 (7)	0.0521 (8)	−0.0003 (7)	0.0200 (7)	0.0022 (6)
C16	0.0502 (9)	0.0520 (9)	0.0534 (9)	−0.0089 (7)	0.0212 (7)	−0.0031 (7)
C17	0.0424 (8)	0.0441 (8)	0.0718 (11)	0.0034 (6)	0.0100 (7)	0.0057 (7)
C18	0.0423 (8)	0.0433 (8)	0.0442 (8)	0.0061 (6)	0.0049 (6)	0.0004 (6)
C19	0.0407 (8)	0.0444 (8)	0.0661 (10)	−0.0025 (6)	0.0144 (7)	0.0063 (7)
O20	0.0977 (12)	0.0435 (7)	0.193 (2)	−0.0191 (7)	0.0773 (13)	−0.0134 (10)
C21	0.0345 (8)	0.0607 (10)	0.0708 (11)	−0.0036 (7)	0.0149 (7)	0.0058 (8)
O22	0.0645 (9)	0.1094 (13)	0.1428 (17)	0.0092 (9)	0.0599 (11)	0.0136 (12)
O1	0.0379 (6)	0.0607 (8)	0.0601 (7)	−0.0024 (5)	0.0034 (5)	−0.0086 (6)

Geometric parameters (Å, º)

O2—C11	1.4248 (19)	N10—C17	1.334 (2)
O2—H2	0.8200	N10—C21	1.336 (2)
C3—C7	1.378 (2)	C11—C18	1.536 (2)
C3—C4	1.384 (2)	C11—H11	0.9800
C3—H3	0.9300	C13—C17	1.381 (2)
C4—C6	1.400 (2)	C13—H13	0.9300
C4—N9	1.478 (2)	C15—C16	1.380 (2)
C5—C13	1.384 (2)	C15—H15	0.9300
C5—C19	1.387 (2)	C16—H16	0.9300
C5—C11	1.518 (2)	C17—H17	0.9300
C6—C15	1.395 (2)	C18—H18A	0.9700
C6—C18	1.510 (2)	C18—H18B	0.9700
C7—C16	1.380 (2)	C19—C21	1.377 (2)
C7—N8	1.474 (2)	C19—H19	0.9300
N8—O14	1.214 (2)	C21—H21	0.9300
N8—O22	1.216 (2)	O1—H1A	0.80 (2)
N9—O20	1.207 (2)	O1—H1B	0.86 (3)
N9—O12	1.2113 (19)
C11—O2—H2	109.5	C5—C11—H11	109.3
C7—C3—C4	117.52 (14)	C18—C11—H11	109.3
C7—C3—H3	121.2	C17—C13—C5	119.26 (14)
C4—C3—H3	121.2	C17—C13—H13	120.4
C3—C4—C6	123.32 (13)	C5—C13—H13	120.4
C3—C4—N9	115.20 (13)	C16—C15—C6	122.89 (15)
C6—C4—N9	121.48 (13)	C16—C15—H15	118.6
C13—C5—C19	117.41 (14)	C6—C15—H15	118.6
C13—C5—C11	121.77 (13)	C15—C16—C7	118.20 (14)
C19—C5—C11	120.79 (14)	C15—C16—H16	120.9
C15—C6—C4	115.76 (13)	C7—C16—H16	120.9
C15—C6—C18	118.25 (14)	N10—C17—C13	123.82 (16)
C4—C6—C18	125.94 (13)	N10—C17—H17	118.1
C3—C7—C16	122.26 (14)	C13—C17—H17	118.1
C3—C7—N8	118.34 (15)	C6—C18—C11	113.58 (12)
C16—C7—N8	119.40 (14)	C6—C18—H18A	108.8
O14—N8—O22	124.18 (16)	C11—C18—H18A	108.8
O14—N8—C7	118.42 (15)	C6—C18—H18B	108.8
O22—N8—C7	117.39 (17)	C11—C18—H18B	108.8
O20—N9—O12	123.07 (15)	H18A—C18—H18B	107.7
O20—N9—C4	117.22 (14)	C21—C19—C5	119.22 (15)
O12—N9—C4	119.71 (13)	C21—C19—H19	120.4
C17—N10—C21	116.36 (14)	C5—C19—H19	120.4
O2—C11—C5	112.04 (13)	N10—C21—C19	123.92 (15)
O2—C11—C18	108.06 (12)	N10—C21—H21	118.0
C5—C11—C18	108.88 (11)	C19—C21—H21	118.0
O2—C11—H11	109.3	H1A—O1—H1B	106 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2^i	0.80 (2)	2.01 (2)	2.801 (3)	173 (2)
O1—H1B···N10^ii	0.86 (3)	2.00 (3)	2.841 (3)	166.1 (19)
O2—H2···O1^iii	0.82	1.85	2.666 (3)	175
C17—H17···O20^iv	0.93	2.53	3.226 (4)	131

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