N-(2,4-Dimethyl­phen­yl)-N′-(3-pyrid­yl)urea monohydrate

In the title compound, C₁₄H₁₅N₃O·H₂O, the water mol­ecule bridges three organic mol­ecules via four inter­molecular hydrogen bonds, leading to supra­molecular tapes that are further cross-linked to form layers.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.149
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT031_ALERT_4_B Refined Extinction Parameter within Range ......       1.65 Sigma

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C9     -   C10     ..       5.25 su
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C13
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C14

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   3 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); 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, 1999); software used to prepare material for publication: SHELXTL (Bruker, 1998).

N-(2,4-Dimethylphenyl)-N'-(3-pyridyl)urea monohydrate

Crystal data

C14H15N3O·H2O	F(000) = 552
Mr = 259.31	Dx = 1.273 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1788 reflections
a = 6.9265 (6) Å	θ = 2.8–22.6°
b = 13.3777 (11) Å	µ = 0.09 mm^−1
c = 14.8549 (12) Å	T = 293 K
β = 100.563 (1)°	Plate, colourless
V = 1353.1 (2) Å^3	0.41 × 0.31 × 0.16 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2400 independent reflections
Radiation source: fine-focus sealed tube	1691 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 25.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −8→8
Tmin = 0.966, Tmax = 0.987	k = −12→15
6758 measured reflections	l = −17→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.149	w = 1/[σ^2(Fo^2) + (0.0712P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.38	(Δ/σ)max < 0.001
2400 reflections	Δρmax = 0.22 e Å^−3
179 parameters	Δρmin = −0.15 e Å^−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (17)

Special details

Experimental. Spectroscopic analysis: ¹H NMR (DMSO-d₆, δ, p.p.m.): 9.14 (s, 1H, NH), 8.60 (d, 1H, py-H2), 8.18 (dd, 1H, py-H6, J = 4.4 and 3.6 Hz), 8.00 (s, 1H, NH), 7.96 (m, 1H, J = 8.4, 3.6 and 2.0 Hz, py-H4), 7.63 (d, 1H, J = 8.0 Hz, Ar—H6'), 7.31 (dd, 1H, J = 8.4 and 4.4 Hz, py-H5), 7.00 (s, 1H, Ar—H3'), 6.96 (d, 1H, J = 8.0 Hz, Ar—H5'), 2.23 (s, 3H, CH₃), 2.20 (s, 3H, CH₃); ¹³C NMR (DMSO-d₆, δ, p.p.m.): 152.81 (C═O), 142.61, 139.76, 136.68, 134.43, 132.06, 130.74, 128.25, 126.59, 124.81, 123.59, 121.82, 20.32, 17.74 (CH₃); IR (KBr, ν, cm^-1): 3296, 3033, 1639, 1589, 1557, 1479, 811, 708.

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
N1	1.3024 (3)	0.90074 (12)	0.18274 (12)	0.0691 (5)
N2	1.1297 (2)	0.64530 (11)	0.14701 (10)	0.0533 (4)
H2A	1.2431	0.6196	0.1673	0.064*
N3	1.0388 (2)	0.48340 (11)	0.12098 (10)	0.0545 (4)
H3B	1.1637	0.4739	0.1303	0.065*
O1	0.80471 (19)	0.60583 (9)	0.10887 (11)	0.0713 (5)
O2	0.4799 (2)	0.53421 (12)	0.19021 (11)	0.0768 (5)
C5	1.1485 (3)	0.95114 (17)	0.13904 (16)	0.0795 (7)
H5A	1.1555	1.0205	0.1379	0.095*
C4	0.9809 (3)	0.90606 (16)	0.09588 (18)	0.0825 (7)
H4A	0.8770	0.9446	0.0660	0.099*
C3	0.9647 (3)	0.80358 (14)	0.09625 (14)	0.0648 (6)
H3A	0.8510	0.7719	0.0668	0.078*
C2	1.1210 (2)	0.74945 (13)	0.14132 (10)	0.0480 (5)
C1	1.2866 (3)	0.80209 (14)	0.18313 (13)	0.0586 (5)
H1A	1.3933	0.7656	0.2134	0.070*
C6	0.9774 (3)	0.57988 (13)	0.12374 (12)	0.0508 (5)
C7	0.9185 (2)	0.39665 (12)	0.10429 (11)	0.0479 (5)
C12	0.7299 (3)	0.40033 (14)	0.05401 (12)	0.0555 (5)
H12A	0.6789	0.4607	0.0293	0.067*
C11	0.6169 (3)	0.31471 (14)	0.04025 (13)	0.0604 (5)
H11A	0.4900	0.3185	0.0065	0.073*
C10	0.6880 (3)	0.22385 (14)	0.07537 (13)	0.0569 (5)
C9	0.8789 (3)	0.22172 (14)	0.12365 (13)	0.0575 (5)
H9A	0.9301	0.1608	0.1469	0.069*
C8	0.9977 (3)	0.30573 (12)	0.13924 (12)	0.0500 (5)
C13	1.2042 (3)	0.29764 (15)	0.19207 (14)	0.0682 (6)
H13A	1.2313	0.2295	0.2103	0.102*
H13B	1.2184	0.3393	0.2455	0.102*
H13C	1.2947	0.3190	0.1541	0.102*
C14	0.5640 (3)	0.13061 (16)	0.06151 (17)	0.0839 (7)
H14B	0.4367	0.1466	0.0269	0.126*
H14C	0.5502	0.1039	0.1200	0.126*
H14D	0.6261	0.0820	0.0288	0.126*
H2C	0.573 (2)	0.5571 (16)	0.1666 (13)	0.080*
H2B	0.528 (3)	0.4911 (14)	0.2309 (12)	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0571 (11)	0.0526 (11)	0.0930 (12)	−0.0078 (8)	0.0019 (9)	−0.0029 (8)
N2	0.0365 (9)	0.0425 (9)	0.0766 (10)	0.0009 (6)	−0.0012 (7)	0.0002 (7)
N3	0.0357 (8)	0.0437 (9)	0.0811 (10)	−0.0013 (7)	0.0026 (7)	0.0021 (7)
O1	0.0363 (8)	0.0523 (9)	0.1223 (12)	0.0022 (6)	0.0062 (7)	0.0035 (7)
O2	0.0455 (9)	0.0815 (11)	0.1025 (12)	0.0171 (7)	0.0110 (7)	0.0244 (8)
C5	0.0713 (16)	0.0469 (13)	0.1156 (18)	−0.0050 (11)	0.0050 (13)	0.0001 (11)
C4	0.0626 (14)	0.0517 (14)	0.1227 (19)	0.0035 (10)	−0.0106 (13)	0.0134 (12)
C3	0.0501 (12)	0.0507 (12)	0.0861 (14)	−0.0019 (9)	−0.0073 (10)	0.0060 (9)
C2	0.0415 (10)	0.0458 (11)	0.0556 (10)	−0.0004 (7)	0.0057 (8)	0.0009 (8)
C1	0.0453 (11)	0.0522 (12)	0.0745 (12)	−0.0034 (8)	0.0006 (9)	0.0012 (9)
C6	0.0387 (10)	0.0475 (11)	0.0638 (11)	0.0003 (8)	0.0033 (8)	0.0037 (8)
C7	0.0417 (10)	0.0450 (11)	0.0575 (10)	−0.0014 (8)	0.0105 (8)	−0.0018 (7)
C12	0.0462 (11)	0.0498 (11)	0.0663 (11)	−0.0020 (8)	−0.0006 (9)	0.0029 (8)
C11	0.0461 (11)	0.0615 (13)	0.0701 (12)	−0.0060 (9)	0.0012 (9)	−0.0042 (9)
C10	0.0503 (12)	0.0507 (12)	0.0698 (11)	−0.0067 (9)	0.0111 (9)	−0.0066 (8)
C9	0.0595 (12)	0.0436 (11)	0.0702 (12)	0.0027 (9)	0.0140 (10)	0.0025 (8)
C8	0.0434 (10)	0.0465 (11)	0.0600 (11)	0.0027 (8)	0.0098 (8)	0.0009 (8)
C13	0.0515 (13)	0.0595 (13)	0.0901 (15)	0.0098 (9)	0.0035 (11)	0.0106 (10)
C14	0.0739 (16)	0.0608 (14)	0.1140 (18)	−0.0161 (11)	0.0092 (14)	−0.0091 (12)

Geometric parameters (Å, º)

N1—C1	1.324 (2)	C1—H1A	0.9300
N1—C5	1.326 (3)	C7—C12	1.381 (2)
N2—C6	1.365 (2)	C7—C8	1.395 (2)
N2—C2	1.396 (2)	C12—C11	1.381 (3)
N2—H2A	0.8600	C12—H12A	0.9300
N3—C6	1.362 (2)	C11—C10	1.378 (3)
N3—C7	1.424 (2)	C11—H11A	0.9300
N3—H3B	0.8600	C10—C9	1.384 (3)
O1—C6	1.226 (2)	C10—C14	1.507 (3)
O2—H2C	0.844 (9)	C9—C8	1.387 (2)
O2—H2B	0.858 (9)	C9—H9A	0.9300
C5—C4	1.360 (3)	C8—C13	1.504 (3)
C5—H5A	0.9300	C13—H13A	0.9600
C4—C3	1.376 (3)	C13—H13B	0.9600
C4—H4A	0.9300	C13—H13C	0.9600
C3—C2	1.371 (2)	C14—H14B	0.9600
C3—H3A	0.9300	C14—H14C	0.9600
C2—C1	1.392 (2)	C14—H14D	0.9600
C1—N1—C5	116.69 (18)	C8—C7—N3	117.93 (15)
C6—N2—C2	126.97 (15)	C11—C12—C7	120.29 (17)
C6—N2—H2A	116.5	C11—C12—H12A	119.9
C2—N2—H2A	116.5	C7—C12—H12A	119.9
C6—N3—C7	127.01 (14)	C10—C11—C12	121.48 (18)
C6—N3—H3B	116.5	C10—C11—H11A	119.3
C7—N3—H3B	116.5	C12—C11—H11A	119.3
H2C—O2—H2B	108 (2)	C11—C10—C9	117.09 (17)
N1—C5—C4	123.0 (2)	C11—C10—C14	121.57 (19)
N1—C5—H5A	118.5	C9—C10—C14	121.34 (18)
C4—C5—H5A	118.5	C10—C9—C8	123.44 (18)
C5—C4—C3	120.2 (2)	C10—C9—H9A	118.3
C5—C4—H4A	119.9	C8—C9—H9A	118.3
C3—C4—H4A	119.9	C9—C8—C7	117.61 (17)
C2—C3—C4	118.07 (19)	C9—C8—C13	120.49 (16)
C2—C3—H3A	121.0	C7—C8—C13	121.90 (16)
C4—C3—H3A	121.0	C8—C13—H13A	109.5
C3—C2—C1	117.60 (18)	C8—C13—H13B	109.5
C3—C2—N2	125.32 (16)	H13A—C13—H13B	109.5
C1—C2—N2	117.07 (15)	C8—C13—H13C	109.5
N1—C1—C2	124.36 (18)	H13A—C13—H13C	109.5
N1—C1—H1A	117.8	H13B—C13—H13C	109.5
C2—C1—H1A	117.8	C10—C14—H14B	109.5
O1—C6—N3	124.23 (16)	C10—C14—H14C	109.5
O1—C6—N2	123.16 (17)	H14B—C14—H14C	109.5
N3—C6—N2	112.60 (15)	C10—C14—H14D	109.5
C12—C7—C8	120.05 (16)	H14B—C14—H14D	109.5
C12—C7—N3	122.01 (15)	H14C—C14—H14D	109.5
C1—N1—C5—C4	−0.2 (3)	C6—N3—C7—C8	−154.52 (17)
N1—C5—C4—C3	0.1 (4)	C8—C7—C12—C11	1.8 (3)
C5—C4—C3—C2	0.2 (3)	N3—C7—C12—C11	−179.21 (16)
C4—C3—C2—C1	−0.5 (3)	C7—C12—C11—C10	−0.3 (3)
C4—C3—C2—N2	−178.92 (19)	C12—C11—C10—C9	−1.2 (3)
C6—N2—C2—C3	−12.3 (3)	C12—C11—C10—C14	179.17 (18)
C6—N2—C2—C1	169.31 (17)	C11—C10—C9—C8	1.2 (3)
C5—N1—C1—C2	−0.1 (3)	C14—C10—C9—C8	−179.10 (18)
C3—C2—C1—N1	0.5 (3)	C10—C9—C8—C7	0.2 (3)
N2—C2—C1—N1	179.04 (17)	C10—C9—C8—C13	−179.77 (16)
C7—N3—C6—O1	−2.5 (3)	C12—C7—C8—C9	−1.7 (3)
C7—N3—C6—N2	176.17 (15)	N3—C7—C8—C9	179.25 (15)
C2—N2—C6—O1	−12.8 (3)	C12—C7—C8—C13	178.24 (16)
C2—N2—C6—N3	168.55 (15)	N3—C7—C8—C13	−0.8 (2)
C6—N3—C7—C12	26.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···N1^i	0.86 (1)	1.98 (1)	2.825 (2)	167 (2)
O2—H2C···O1	0.84 (1)	2.06 (1)	2.905 (2)	177 (2)
C3—H3A···O1	0.93	2.35	2.888 (2)	117
C12—H12A···O1	0.93	2.36	2.887 (2)	116
N2—H2A···O2^ii	0.86	1.98	2.8164 (19)	165
N3—H3B···O2^ii	0.86	2.35	3.115 (2)	148

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