Crystal stucture of methyl 2-({[2-(meth-oxy-carbon-yl)phen-yl]carbamo-yl}amino)-benzoate.

In the title compound, C17H16N2O5, the dihedral angles between the central urea [N-C(=O)-N] fragment and its attached benzene rings are 20.20 (14) and 24.24 (13)°; the dihedral angle between the aromatic rings is 42.1 (1)°. The mol-ecular conformation is consolidated by two intra-molecular N-H⋯O hydrogen bonds, which both generate S(6) rings. In the crystal, inversion dimers linked by pairs of C-H⋯O inter-actions generate R 2 (2)(14) loops. The dimers are linked by further C-H⋯O inter-actions into (011) sheets.

Related literature

For the medical and biological activities of urea derivatives, see: Abad et al. (2004 ▸); Chen et al. (2005 ▸); Batra et al. (2006 ▸). For cytokinin activity, see: Wang et al. (2001 ▸); Ricci et al. (2005 ▸).

Experimental

Crystal data

C17H16N2O5

M = 328.32

Monoclinic,

a = 9.005 (8) Å

b = 23.80 (2) Å

c = 7.400 (7) Å

β = 93.66 (4)°

V = 1583 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.42 × 0.36 × 0.29 mm

Data collection

Bruker X8 APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.693, T max = 0.747

11500 measured reflections

3364 independent reflections

1667 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.137

S = 0.95

3364 reflections

220 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015006465/hb7393sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015006465/hb7393Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015006465/hb7393Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015006465/hb7393fig1.tif

A view of the mol­ecule of the title compound, showing displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989015006465/hb7393fig2.tif

Part of the crystal structure of the title compound, showing hydrogen-bonded (dashed lines) dimers.

CCDC reference: 1056943

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H16N2O5	F(000) = 688
Mr = 328.32	Dx = 1.378 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3364 reflections
a = 9.005 (8) Å	θ = 2.4–26.7°
b = 23.80 (2) Å	µ = 0.10 mm−1
c = 7.400 (7) Å	T = 296 K
β = 93.66 (4)°	Block, yellow
V = 1583 (3) Å3	0.42 × 0.36 × 0.29 mm
Z = 4

Bruker X8 APEXII CCD diffractometer	3364 independent reflections
Radiation source: fine-focus sealed tube	1667 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
φ and ω scans	θmax = 26.7°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→7
Tmin = 0.693, Tmax = 0.747	k = −29→30
11500 measured reflections	l = −9→9

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-atom parameters constrained
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.0578P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95	(Δ/σ)max < 0.001
3364 reflections	Δρmax = 0.21 e Å−3
220 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0052 (11)

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	0.8216 (3)	0.50547 (11)	0.6105 (4)	0.0617 (8)
H1A	0.8796	0.5351	0.5624	0.093*
H1B	0.8023	0.4772	0.5194	0.093*
H1C	0.8755	0.4891	0.7136	0.093*
C2	0.5813 (3)	0.49037 (10)	0.7155 (3)	0.0413 (6)
C3	0.4424 (2)	0.51598 (9)	0.7748 (3)	0.0370 (6)
C4	0.4261 (3)	0.57446 (9)	0.7763 (3)	0.0463 (6)
H4	0.5028	0.5968	0.7377	0.056*
C5	0.3000 (3)	0.59993 (10)	0.8334 (3)	0.0524 (7)
H5	0.2913	0.6389	0.8324	0.063*
C6	0.1861 (3)	0.56676 (10)	0.8925 (3)	0.0496 (7)
H6	0.1012	0.5837	0.9328	0.060*
C7	0.1975 (3)	0.50878 (9)	0.8921 (3)	0.0421 (6)
H7	0.1199	0.4871	0.9315	0.050*
C8	0.3249 (3)	0.48226 (9)	0.8331 (3)	0.0377 (6)
C9	0.2326 (3)	0.38375 (10)	0.8583 (3)	0.0429 (6)
C10	0.2281 (3)	0.27870 (9)	0.8808 (3)	0.0420 (6)
C11	0.0793 (3)	0.27180 (10)	0.8152 (3)	0.0519 (7)
H11	0.0219	0.3031	0.7827	0.062*
C12	0.0181 (3)	0.21894 (11)	0.7988 (4)	0.0607 (8)
H12	−0.0800	0.2150	0.7535	0.073*
C13	0.0991 (3)	0.17166 (11)	0.8482 (4)	0.0627 (8)
H13	0.0560	0.1362	0.8371	0.075*
C14	0.2450 (3)	0.17759 (10)	0.9142 (3)	0.0511 (7)
H14	0.2997	0.1457	0.9478	0.061*
C15	0.3129 (3)	0.23038 (9)	0.9319 (3)	0.0407 (6)
C16	0.4711 (3)	0.23461 (10)	1.0022 (3)	0.0460 (6)
C17	0.6894 (3)	0.18555 (11)	1.1114 (4)	0.0695 (9)
H17A	0.6980	0.2026	1.2292	0.104*
H17B	0.7470	0.2066	1.0300	0.104*
H17C	0.7258	0.1477	1.1196	0.104*
N2	0.2964 (2)	0.33173 (7)	0.8915 (3)	0.0472 (5)
H2N	0.3903	0.3306	0.9209	0.057*
N3	0.3414 (2)	0.42374 (7)	0.8385 (3)	0.0443 (5)
H3N	0.4311	0.4140	0.8169	0.053*
O1	0.68143 (18)	0.52810 (7)	0.6650 (2)	0.0536 (5)
O2	0.60738 (18)	0.44002 (7)	0.7108 (2)	0.0557 (5)
O3	0.0994 (2)	0.39320 (7)	0.8476 (3)	0.0692 (6)
O4	0.5330 (2)	0.18523 (7)	1.0436 (3)	0.0618 (5)
O5	0.5419 (2)	0.27802 (7)	1.0207 (3)	0.0710 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0386 (16)	0.080 (2)	0.0678 (19)	−0.0038 (14)	0.0124 (14)	0.0022 (15)
C2	0.0424 (15)	0.0422 (15)	0.0387 (14)	−0.0047 (12)	−0.0025 (12)	0.0035 (11)
C3	0.0377 (14)	0.0362 (13)	0.0364 (13)	−0.0004 (11)	−0.0018 (11)	0.0031 (10)
C4	0.0503 (16)	0.0346 (13)	0.0536 (16)	−0.0020 (12)	0.0010 (13)	0.0064 (11)
C5	0.0583 (18)	0.0350 (14)	0.0638 (18)	0.0053 (13)	0.0029 (14)	−0.0007 (12)
C6	0.0504 (16)	0.0481 (15)	0.0501 (16)	0.0133 (13)	0.0017 (13)	−0.0014 (12)
C7	0.0438 (15)	0.0390 (14)	0.0435 (15)	0.0014 (12)	0.0039 (12)	0.0005 (11)
C8	0.0414 (14)	0.0359 (13)	0.0352 (13)	0.0003 (11)	−0.0029 (11)	0.0003 (10)
C9	0.0443 (16)	0.0388 (14)	0.0465 (15)	−0.0055 (12)	0.0091 (12)	0.0008 (11)
C10	0.0484 (16)	0.0390 (14)	0.0396 (14)	−0.0089 (12)	0.0111 (12)	0.0001 (10)
C11	0.0528 (18)	0.0471 (16)	0.0561 (17)	−0.0068 (13)	0.0063 (14)	0.0036 (12)
C12	0.0591 (19)	0.0541 (18)	0.0686 (19)	−0.0156 (15)	0.0011 (15)	−0.0027 (14)
C13	0.066 (2)	0.0463 (16)	0.076 (2)	−0.0211 (15)	0.0036 (16)	−0.0101 (14)
C14	0.0626 (19)	0.0346 (14)	0.0570 (17)	−0.0066 (13)	0.0117 (14)	−0.0041 (12)
C15	0.0467 (15)	0.0362 (13)	0.0404 (14)	−0.0069 (11)	0.0115 (12)	−0.0024 (10)
C16	0.0584 (18)	0.0328 (14)	0.0480 (16)	−0.0052 (13)	0.0128 (13)	0.0008 (11)
C17	0.0476 (18)	0.0535 (17)	0.107 (3)	0.0005 (14)	0.0035 (17)	0.0059 (16)
N2	0.0441 (12)	0.0362 (11)	0.0614 (14)	−0.0054 (10)	0.0046 (11)	0.0055 (10)
N3	0.0384 (12)	0.0321 (11)	0.0632 (14)	0.0010 (9)	0.0094 (10)	0.0043 (9)
O1	0.0435 (11)	0.0497 (10)	0.0688 (12)	−0.0056 (8)	0.0134 (9)	0.0033 (8)
O2	0.0486 (11)	0.0416 (10)	0.0780 (13)	0.0030 (9)	0.0137 (9)	−0.0019 (9)
O3	0.0417 (11)	0.0492 (11)	0.1177 (18)	−0.0013 (9)	0.0138 (11)	−0.0042 (10)
O4	0.0544 (12)	0.0369 (10)	0.0938 (15)	−0.0016 (9)	0.0033 (10)	0.0022 (9)
O5	0.0606 (13)	0.0380 (11)	0.1121 (17)	−0.0105 (9)	−0.0126 (12)	0.0073 (10)

C1—O1	1.453 (3)	C10—N2	1.404 (3)
C1—H1A	0.9600	C10—C11	1.405 (4)
C1—H1B	0.9600	C10—C15	1.418 (3)
C1—H1C	0.9600	C11—C12	1.376 (3)
C2—O2	1.222 (3)	C11—H11	0.9300
C2—O1	1.342 (3)	C12—C13	1.377 (4)
C2—C3	1.483 (3)	C12—H12	0.9300
C3—C4	1.400 (3)	C13—C14	1.379 (4)
C3—C8	1.417 (3)	C13—H13	0.9300
C4—C5	1.378 (3)	C14—C15	1.400 (3)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.387 (3)	C15—C16	1.489 (4)
C5—H5	0.9300	C16—O5	1.217 (3)
C6—C7	1.384 (3)	C16—O4	1.328 (3)
C6—H6	0.9300	C17—O4	1.465 (3)
C7—C8	1.403 (3)	C17—H17A	0.9600
C7—H7	0.9300	C17—H17B	0.9600
C8—N3	1.401 (3)	C17—H17C	0.9600
C9—O3	1.218 (3)	N2—H2N	0.8600
C9—N2	1.381 (3)	N3—H3N	0.8646
C9—N3	1.381 (3)
O1—C1—H1A	109.5	C12—C11—C10	120.3 (2)
O1—C1—H1B	109.5	C12—C11—H11	119.8
H1A—C1—H1B	109.5	C10—C11—H11	119.8
O1—C1—H1C	109.5	C11—C12—C13	121.4 (3)
H1A—C1—H1C	109.5	C11—C12—H12	119.3
H1B—C1—H1C	109.5	C13—C12—H12	119.3
O2—C2—O1	121.0 (2)	C12—C13—C14	119.1 (2)
O2—C2—C3	125.3 (2)	C12—C13—H13	120.5
O1—C2—C3	113.7 (2)	C14—C13—H13	120.5
C4—C3—C8	118.7 (2)	C13—C14—C15	121.7 (2)
C4—C3—C2	120.1 (2)	C13—C14—H14	119.2
C8—C3—C2	121.2 (2)	C15—C14—H14	119.2
C5—C4—C3	121.9 (2)	C14—C15—C10	118.6 (2)
C5—C4—H4	119.0	C14—C15—C16	119.7 (2)
C3—C4—H4	119.0	C10—C15—C16	121.7 (2)
C4—C5—C6	119.1 (2)	O5—C16—O4	121.1 (3)
C4—C5—H5	120.4	O5—C16—C15	125.4 (2)
C6—C5—H5	120.4	O4—C16—C15	113.5 (2)
C7—C6—C5	120.7 (2)	O4—C17—H17A	109.5
C7—C6—H6	119.6	O4—C17—H17B	109.5
C5—C6—H6	119.6	H17A—C17—H17B	109.5
C6—C7—C8	120.8 (2)	O4—C17—H17C	109.5
C6—C7—H7	119.6	H17A—C17—H17C	109.5
C8—C7—H7	119.6	H17B—C17—H17C	109.5
N3—C8—C7	121.7 (2)	C9—N2—C10	128.3 (2)
N3—C8—C3	119.4 (2)	C9—N2—H2N	117.6
C7—C8—C3	118.7 (2)	C10—N2—H2N	114.0
O3—C9—N2	125.1 (2)	C9—N3—C8	127.8 (2)
O3—C9—N3	124.7 (2)	C9—N3—H3N	120.8
N2—C9—N3	110.3 (2)	C8—N3—H3N	111.1
N2—C10—C11	122.0 (2)	C2—O1—C1	116.1 (2)
N2—C10—C15	119.2 (2)	C16—O4—C17	117.03 (19)
C11—C10—C15	118.8 (2)
O2—C2—C3—C4	179.2 (2)	C13—C14—C15—C16	−179.4 (2)
O1—C2—C3—C4	−0.7 (3)	N2—C10—C15—C14	−177.6 (2)
O2—C2—C3—C8	0.1 (3)	C11—C10—C15—C14	0.3 (3)
O1—C2—C3—C8	−179.83 (19)	N2—C10—C15—C16	2.0 (3)
C8—C3—C4—C5	0.3 (3)	C11—C10—C15—C16	179.9 (2)
C2—C3—C4—C5	−178.9 (2)	C14—C15—C16—O5	178.9 (2)
C3—C4—C5—C6	0.5 (4)	C10—C15—C16—O5	−0.8 (4)
C4—C5—C6—C7	−0.9 (4)	C14—C15—C16—O4	−0.5 (3)
C5—C6—C7—C8	0.4 (3)	C10—C15—C16—O4	179.9 (2)
C6—C7—C8—N3	177.4 (2)	O3—C9—N2—C10	15.1 (4)
C6—C7—C8—C3	0.4 (3)	N3—C9—N2—C10	−164.8 (2)
C4—C3—C8—N3	−177.8 (2)	C11—C10—N2—C9	6.1 (4)
C2—C3—C8—N3	1.4 (3)	C15—C10—N2—C9	−176.1 (2)
C4—C3—C8—C7	−0.8 (3)	O3—C9—N3—C8	11.5 (4)
C2—C3—C8—C7	178.4 (2)	N2—C9—N3—C8	−168.6 (2)
N2—C10—C11—C12	177.0 (2)	C7—C8—N3—C9	16.1 (3)
C15—C10—C11—C12	−0.9 (4)	C3—C8—N3—C9	−167.0 (2)
C10—C11—C12—C13	1.0 (4)	O2—C2—O1—C1	−1.7 (3)
C11—C12—C13—C14	−0.5 (4)	C3—C2—O1—C1	178.3 (2)
C12—C13—C14—C15	−0.2 (4)	O5—C16—O4—C17	−0.2 (4)
C13—C14—C15—C10	0.2 (4)	C15—C16—O4—C17	179.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O5	0.86	1.96	2.677 (3)	140
N3—H3N···O2	0.86	1.92	2.659 (3)	144
C6—H6···O3i	0.93	2.57	3.442 (4)	157
C17—H17C···O2ii	0.96	2.46	3.176 (4)	132

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N2H2NO5	0.86	1.96	2.677(3)	140
N3H3NO2	0.86	1.92	2.659(3)	144
C6H6O3i	0.93	2.57	3.442(4)	157
C17H17CO2ii	0.96	2.46	3.176(4)	132

Symmetry codes: (i) ; (ii) .