N-{2-[N-(4-Methyl-phen-yl)oxamo-yl]phen-yl}propanamide.

The title compound, C(18)H(18)N(2)O(3), is the product of the heterocyclic ring cleavage at position 2 of 1-propionylisatin. Two centrosymmetric cyclic motifs, viz. R(2) (2)(14) and R(2) (2)(18), are formed by N-H⋯O hydrogen bonds with the propanamide and amino-phenyl units, respectively, as the N-H donors. These motifs combine into two C(2) (2)(8) chain motifs parallel to the b axis. The chain structure is stabilized by C-H⋯π inter-actions between the benzene rings, where C-H is from the phenyl ring of the cleaved part of 1-pro-pionylisatin.

Related literature

For related structures, see: Hohne & Seidel (1979 ▶); Boryczka et al. (1998 ▶); Zukerman-Schpector et al. (1994 ▶). For synthetic background, see: Pervez et al. (2009 ▶, 2010a ▶,b ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H18N2O3

M = 310.34

Triclinic,

a = 9.2048 (4) Å

b = 9.7717 (3) Å

c = 10.4404 (4) Å

α = 72.962 (2)°

β = 72.920 (1)°

γ = 69.285 (2)°

V = 820.63 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.32 × 0.24 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.942, T max = 0.952

11476 measured reflections

2933 independent reflections

2402 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.111

S = 1.03

2933 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023263/gk2285sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023263/gk2285Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H18N2O3	Z = 2
Mr = 310.34	F(000) = 328
Triclinic, P1	Dx = 1.254 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2048 (4) Å	Cell parameters from 2402 reflections
b = 9.7717 (3) Å	θ = 2.8–25.3°
c = 10.4404 (4) Å	µ = 0.09 mm−1
α = 72.962 (2)°	T = 296 K
β = 72.920 (1)°	Prism, yellow
γ = 69.285 (2)°	0.32 × 0.24 × 0.22 mm
V = 820.63 (6) Å3

Bruker Kappa APEXII CCD diffractometer	2933 independent reflections
Radiation source: fine-focus sealed tube	2402 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 8.2 pixels mm-1	θmax = 25.3°, θmin = 2.8°
ω scans	h = −11→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
Tmin = 0.942, Tmax = 0.952	l = −12→12
11476 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0538P)2 + 0.1939P] where P = (Fo2 + 2Fc2)/3
2933 reflections	(Δ/σ)max < 0.001
210 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.73296 (14)	0.26832 (11)	0.51591 (11)	0.0532 (4)
O2	0.60422 (14)	−0.02427 (11)	0.72653 (12)	0.0527 (4)
O3	0.36026 (15)	0.18977 (12)	0.55159 (12)	0.0572 (4)
N1	0.73440 (15)	0.06472 (13)	0.45212 (13)	0.0454 (4)
N2	0.36473 (15)	0.41064 (13)	0.57412 (12)	0.0434 (4)
C1	0.81861 (17)	0.09987 (16)	0.31438 (16)	0.0423 (5)
C2	0.7508 (2)	0.11442 (19)	0.20806 (17)	0.0533 (6)
C3	0.8280 (2)	0.1562 (2)	0.07434 (18)	0.0584 (6)
C4	0.9720 (2)	0.18504 (18)	0.04359 (18)	0.0541 (6)
C5	1.0394 (2)	0.1665 (2)	0.15214 (19)	0.0585 (6)
C6	0.96495 (19)	0.12374 (19)	0.28597 (18)	0.0533 (6)
C7	1.0503 (3)	0.2377 (3)	−0.1028 (2)	0.0789 (8)
C8	0.69138 (17)	0.15593 (15)	0.53889 (15)	0.0396 (5)
C9	0.58882 (17)	0.10771 (15)	0.67838 (15)	0.0404 (5)
C10	0.49283 (17)	0.22541 (16)	0.75877 (14)	0.0394 (4)
C11	0.5065 (2)	0.19194 (19)	0.89436 (16)	0.0503 (5)
C12	0.4344 (2)	0.2961 (2)	0.97574 (17)	0.0606 (6)
C13	0.3468 (2)	0.4365 (2)	0.92194 (18)	0.0619 (6)
C14	0.3263 (2)	0.47161 (18)	0.78955 (17)	0.0513 (5)
C15	0.39731 (17)	0.36707 (15)	0.70660 (14)	0.0390 (4)
C16	0.33857 (18)	0.32494 (17)	0.50734 (16)	0.0444 (5)
C17	0.2851 (3)	0.4048 (2)	0.3751 (2)	0.0701 (7)
C18	0.1504 (3)	0.3664 (3)	0.3605 (3)	0.0991 (10)
H1	0.71043	−0.01814	0.48038	0.0544*
H2	0.65336	0.09623	0.22615	0.0639*
H2A	0.36115	0.50119	0.53138	0.0521*
H3	0.78158	0.16501	0.00316	0.0701*
H5	1.13748	0.18326	0.13421	0.0702*
H6	1.01320	0.11098	0.35712	0.0640*
H7A	1.16236	0.18772	−0.11688	0.1184*
H7B	1.03271	0.34386	−0.12098	0.1184*
H7C	1.00549	0.21520	−0.16359	0.1184*
H11	0.56593	0.09679	0.93107	0.0604*
H12	0.44498	0.27149	1.06627	0.0727*
H13	0.30103	0.50856	0.97527	0.0744*
H14	0.26406	0.56636	0.75514	0.0616*
H17A	0.25468	0.51191	0.36884	0.0841*
H17B	0.37380	0.38080	0.29937	0.0841*
H18A	0.06159	0.39040	0.43466	0.1487*
H18B	0.18084	0.26134	0.36232	0.1487*
H18C	0.12098	0.42260	0.27493	0.1487*

	U11	U22	U33	U12	U13	U23
O1	0.0656 (7)	0.0375 (6)	0.0605 (7)	−0.0269 (5)	−0.0023 (5)	−0.0126 (5)
O2	0.0635 (7)	0.0321 (5)	0.0596 (7)	−0.0167 (5)	−0.0155 (5)	0.0002 (5)
O3	0.0757 (8)	0.0411 (6)	0.0698 (8)	−0.0238 (5)	−0.0319 (6)	−0.0087 (5)
N1	0.0516 (8)	0.0360 (6)	0.0531 (8)	−0.0213 (6)	−0.0045 (6)	−0.0122 (5)
N2	0.0566 (8)	0.0321 (6)	0.0465 (7)	−0.0200 (5)	−0.0182 (6)	0.0002 (5)
C1	0.0417 (8)	0.0338 (7)	0.0522 (9)	−0.0120 (6)	−0.0048 (7)	−0.0143 (6)
C2	0.0465 (9)	0.0610 (10)	0.0617 (11)	−0.0255 (8)	−0.0069 (8)	−0.0191 (8)
C3	0.0581 (11)	0.0693 (11)	0.0555 (10)	−0.0246 (9)	−0.0114 (8)	−0.0176 (8)
C4	0.0508 (10)	0.0466 (9)	0.0596 (10)	−0.0144 (7)	−0.0001 (8)	−0.0152 (7)
C5	0.0408 (9)	0.0644 (11)	0.0714 (12)	−0.0227 (8)	−0.0031 (8)	−0.0159 (9)
C6	0.0442 (9)	0.0586 (10)	0.0622 (11)	−0.0185 (8)	−0.0124 (8)	−0.0147 (8)
C7	0.0777 (14)	0.0777 (14)	0.0698 (13)	−0.0306 (11)	0.0063 (11)	−0.0111 (10)
C8	0.0420 (8)	0.0293 (7)	0.0491 (9)	−0.0116 (6)	−0.0126 (7)	−0.0061 (6)
C9	0.0439 (8)	0.0325 (7)	0.0494 (9)	−0.0153 (6)	−0.0170 (7)	−0.0032 (6)
C10	0.0423 (8)	0.0368 (7)	0.0419 (8)	−0.0184 (6)	−0.0089 (6)	−0.0040 (6)
C11	0.0582 (10)	0.0475 (9)	0.0462 (9)	−0.0181 (7)	−0.0179 (8)	−0.0013 (7)
C12	0.0765 (12)	0.0680 (12)	0.0415 (9)	−0.0242 (10)	−0.0147 (8)	−0.0118 (8)
C13	0.0784 (13)	0.0568 (10)	0.0527 (10)	−0.0194 (9)	−0.0076 (9)	−0.0215 (8)
C14	0.0591 (10)	0.0386 (8)	0.0556 (10)	−0.0141 (7)	−0.0101 (8)	−0.0115 (7)
C15	0.0436 (8)	0.0345 (7)	0.0428 (8)	−0.0189 (6)	−0.0098 (6)	−0.0039 (6)
C16	0.0481 (9)	0.0417 (8)	0.0497 (9)	−0.0199 (7)	−0.0148 (7)	−0.0063 (7)
C17	0.0917 (14)	0.0686 (12)	0.0623 (12)	−0.0303 (11)	−0.0355 (11)	−0.0043 (9)
C18	0.1088 (19)	0.0778 (15)	0.133 (2)	−0.0164 (13)	−0.0782 (18)	−0.0158 (14)

O1—C8	1.2244 (19)	C12—C13	1.371 (3)
O2—C9	1.2119 (18)	C13—C14	1.376 (2)
O3—C16	1.228 (2)	C14—C15	1.391 (2)
N1—C1	1.425 (2)	C16—C17	1.501 (3)
N1—C8	1.3359 (19)	C17—C18	1.475 (4)
N2—C15	1.4116 (19)	C2—H2	0.9300
N2—C16	1.352 (2)	C3—H3	0.9300
N1—H1	0.8600	C5—H5	0.9300
N2—H2A	0.8600	C6—H6	0.9300
C1—C6	1.380 (3)	C7—H7A	0.9600
C1—C2	1.376 (2)	C7—H7B	0.9600
C2—C3	1.382 (2)	C7—H7C	0.9600
C3—C4	1.379 (3)	C11—H11	0.9300
C4—C7	1.508 (3)	C12—H12	0.9300
C4—C5	1.384 (3)	C13—H13	0.9300
C5—C6	1.376 (3)	C14—H14	0.9300
C8—C9	1.529 (2)	C17—H17A	0.9700
C9—C10	1.490 (2)	C17—H17B	0.9700
C10—C11	1.390 (2)	C18—H18A	0.9600
C10—C15	1.402 (2)	C18—H18B	0.9600
C11—C12	1.377 (2)	C18—H18C	0.9600
O1···N2	3.1213 (19)	C3···H13i	3.0000
O1···C6	3.027 (2)	C6···H14i	3.0100
O1···C15	3.138 (2)	C8···H6	2.9700
O1···N2i	2.8821 (16)	C10···H7Avi	3.0400
O2···N1	2.7678 (17)	C11···H11iii	3.0500
O2···O3	3.0986 (18)	C11···H3vii	2.9700
O3···C8	2.914 (2)	C12···H3vii	3.0600
O3···N1ii	2.9247 (18)	C15···H7Avi	3.1000
O3···C10	2.930 (2)	H1···O2	2.4600
O3···C9	2.577 (2)	H1···O3ii	2.1400
O3···N1	3.178 (2)	H1···H18Bii	2.5200
O3···O2	3.0986 (18)	H2···O2ii	2.5800
O1···H6	2.8200	H2A···H14	2.4300
O1···H14i	2.8200	H2A···H17A	2.1600
O1···H17Ai	2.8000	H2A···O1i	2.0700
O1···H2Ai	2.0700	H2A···N2i	2.7700
O2···H12iii	2.8000	H2A···H2Ai	2.4400
O2···H1	2.4600	H3···C11viii	2.9700
O2···H11	2.6100	H3···C12viii	3.0600
O2···H2ii	2.5800	H3···H7C	2.3700
O2···H5iv	2.8800	H5···H7A	2.5500
O2···H18Bii	2.6600	H5···O2iv	2.8800
O3···H18B	2.7200	H6···O1	2.8200
O3···H1ii	2.1400	H6···C8	2.9700
N1···O2	2.7678 (17)	H6···H18Bix	2.5000
N1···O3	3.178 (2)	H7A···C10x	3.0400
N1···O3ii	2.9247 (18)	H7A···C15x	3.1000
N2···O1	3.1213 (19)	H7A···H5	2.5500
N2···C8	3.157 (2)	H7B···H18Cxi	2.5900
N2···O1i	2.8821 (16)	H7C···H3	2.3700
N2···N2i	3.298 (2)	H11···O2	2.6100
N2···H2Ai	2.7700	H11···C11iii	3.0500
C3···C4v	3.572 (3)	H11···H11iii	2.4700
C3···C7v	3.554 (3)	H12···O2iii	2.8000
C4···C3v	3.572 (3)	H13···C3i	3.0000
C6···O1	3.027 (2)	H14···H2A	2.4300
C7···C3v	3.554 (3)	H14···O1i	2.8200
C8···C16	3.146 (2)	H14···C1i	2.9900
C8···N2	3.157 (2)	H14···C6i	3.0100
C8···O3	2.914 (2)	H17A···H2A	2.1600
C9···C16	3.120 (2)	H17A···O1i	2.8000
C9···O3	2.577 (2)	H18B···O3	2.7200
C10···O3	2.930 (2)	H18B···H6xii	2.5000
C15···O1	3.138 (2)	H18B···O2ii	2.6600
C16···C8	3.146 (2)	H18B···H1ii	2.5200
C16···C9	3.120 (2)	H18C···H7Bxi	2.5900
C1···H14i	2.9900
C1—N1—C8	122.33 (13)	C16—C17—C18	113.78 (19)
C15—N2—C16	126.83 (13)	C1—C2—H2	120.00
C8—N1—H1	119.00	C3—C2—H2	120.00
C1—N1—H1	119.00	C2—C3—H3	119.00
C16—N2—H2A	117.00	C4—C3—H3	119.00
C15—N2—H2A	117.00	C4—C5—H5	119.00
C2—C1—C6	119.50 (16)	C6—C5—H5	119.00
N1—C1—C6	121.04 (15)	C1—C6—H6	120.00
N1—C1—C2	119.43 (16)	C5—C6—H6	120.00
C1—C2—C3	119.74 (18)	C4—C7—H7A	109.00
C2—C3—C4	121.78 (18)	C4—C7—H7B	109.00
C3—C4—C7	120.86 (19)	C4—C7—H7C	109.00
C5—C4—C7	121.7 (2)	H7A—C7—H7B	109.00
C3—C4—C5	117.39 (17)	H7A—C7—H7C	110.00
C4—C5—C6	121.66 (19)	H7B—C7—H7C	109.00
C1—C6—C5	119.89 (17)	C10—C11—H11	119.00
O1—C8—N1	124.88 (14)	C12—C11—H11	119.00
N1—C8—C9	115.40 (13)	C11—C12—H12	120.00
O1—C8—C9	119.66 (13)	C13—C12—H12	120.00
O2—C9—C8	119.57 (13)	C12—C13—H13	120.00
O2—C9—C10	122.47 (14)	C14—C13—H13	120.00
C8—C9—C10	117.22 (12)	C13—C14—H14	120.00
C11—C10—C15	118.54 (14)	C15—C14—H14	120.00
C9—C10—C11	116.22 (14)	C16—C17—H17A	109.00
C9—C10—C15	125.18 (13)	C16—C17—H17B	109.00
C10—C11—C12	121.67 (16)	C18—C17—H17A	109.00
C11—C12—C13	119.31 (16)	C18—C17—H17B	109.00
C12—C13—C14	120.45 (17)	H17A—C17—H17B	108.00
C13—C14—C15	120.80 (16)	C17—C18—H18A	109.00
N2—C15—C10	123.90 (13)	C17—C18—H18B	109.00
N2—C15—C14	116.97 (13)	C17—C18—H18C	109.00
C10—C15—C14	119.12 (14)	H18A—C18—H18B	109.00
O3—C16—C17	122.47 (16)	H18A—C18—H18C	109.00
N2—C16—C17	115.84 (14)	H18B—C18—H18C	109.00
O3—C16—N2	121.68 (15)
C8—N1—C1—C2	−118.93 (18)	N1—C8—C9—C10	−159.46 (15)
C8—N1—C1—C6	59.2 (2)	O1—C8—C9—O2	−147.04 (17)
C1—N1—C8—O1	−8.3 (3)	C8—C9—C10—C15	47.4 (2)
C1—N1—C8—C9	174.65 (14)	O2—C9—C10—C11	40.4 (2)
C15—N2—C16—O3	−9.2 (3)	O2—C9—C10—C15	−142.61 (18)
C16—N2—C15—C10	38.2 (3)	C8—C9—C10—C11	−129.66 (17)
C16—N2—C15—C14	−140.31 (18)	C15—C10—C11—C12	−2.8 (3)
C15—N2—C16—C17	172.10 (17)	C9—C10—C15—N2	7.8 (3)
C2—C1—C6—C5	2.1 (3)	C9—C10—C15—C14	−173.71 (16)
N1—C1—C2—C3	176.60 (15)	C9—C10—C11—C12	174.46 (17)
C6—C1—C2—C3	−1.6 (3)	C11—C10—C15—N2	−175.24 (16)
N1—C1—C6—C5	−176.03 (15)	C11—C10—C15—C14	3.3 (3)
C1—C2—C3—C4	−0.4 (3)	C10—C11—C12—C13	0.0 (3)
C2—C3—C4—C7	−177.02 (19)	C11—C12—C13—C14	2.3 (3)
C2—C3—C4—C5	1.8 (3)	C12—C13—C14—C15	−1.8 (3)
C3—C4—C5—C6	−1.2 (3)	C13—C14—C15—N2	177.53 (17)
C7—C4—C5—C6	177.57 (19)	C13—C14—C15—C10	−1.1 (3)
C4—C5—C6—C1	−0.7 (3)	O3—C16—C17—C18	47.0 (3)
O1—C8—C9—C10	23.3 (2)	N2—C16—C17—C18	−134.27 (19)
N1—C8—C9—O2	30.2 (2)

Cg1 is the centroid of C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	2.46	2.7678 (17)	102
N1—H1···O3ii	0.86	2.14	2.9247 (18)	152
N2—H2A···O1i	0.86	2.07	2.8821 (16)	157
C2—H2···O2ii	0.93	2.58	3.506 (2)	175
C14—H14···Cg1i	0.93	2.89	3.6693 (18)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	2.46	2.7678 (17)	102
N1—H1⋯O3i	0.86	2.14	2.9247 (18)	152
N2—H2A⋯O1ii	0.86	2.07	2.8821 (16)	157
C2—H2⋯O2i	0.93	2.58	3.506 (2)	175
C14—H14⋯Cg1ii	0.93	2.89	3.6693 (18)	142

Symmetry codes: (i) ; (ii) .