3-(Phenyl-imino)indolin-2-one.

The imino C=N double bond in the title compound, C(14)H(10)N(2)O, exists in an E conformation, with the phenyl ring being twisted by 80.7 (1)° in one independent mol-ecule and by 81.4 (1)° in the other with respect to the plane of the indoline fused-ring system. The two independent mol-ecules are linked by N-H⋯O hydrogen bonds, forming a zigzag chain running along the a axis.

Related literature

For the synthesis, see: Grimshaw & Begley (1974 ▶). For the crystal structures of other phenyl-substituted derivatives, see: Akkurt et al. (2003 ▶); Hökelek et al. (2006 ▶); Öztürk et al. (2003 ▶).

Experimental

Crystal data

C14H10N2O

M = 222.24

Orthorhombic,

a = 20.1647 (4) Å

b = 5.0223 (1) Å

c = 21.8791 (5) Å

V = 2215.77 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.3 × 0.3 × 0.3 mm

Data collection

Bruker APEXII diffractometer

15055 measured reflections

2619 independent reflections

2042 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.118

S = 1.10

2619 reflections

315 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681000259X/bt5177sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000259X/bt5177Isup2.hkl

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

C14H10N2O	F(000) = 928
Mr = 222.24	Dx = 1.332 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3521 reflections
a = 20.1647 (4) Å	θ = 2.7–25.7°
b = 5.0223 (1) Å	µ = 0.09 mm−1
c = 21.8791 (5) Å	T = 293 K
V = 2215.77 (8) Å3	Block, orange
Z = 8	0.3 × 0.3 × 0.3 mm

Bruker APEXII diffractometer	2042 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
graphite	θmax = 27.5°, θmin = 1.9°
φ and ω scans	h = −24→26
15055 measured reflections	k = −3→6
2619 independent reflections	l = −28→28

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0745P)2 + 0.0171P] where P = (Fo2 + 2Fc2)/3
2619 reflections	(Δ/σ)max = 0.001
315 parameters	Δρmax = 0.19 e Å−3
3 restraints	Δρmin = −0.20 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.36628 (12)	0.9072 (6)	0.49888 (10)	0.0769 (7)
O2	0.11993 (12)	0.6636 (6)	0.52675 (12)	0.0816 (8)
N1	0.44843 (11)	0.6264 (6)	0.53285 (11)	0.0543 (6)
N2	0.28865 (11)	0.6607 (5)	0.59271 (10)	0.0505 (6)
N3	0.20427 (11)	0.9352 (5)	0.49173 (10)	0.0535 (6)
N4	0.04413 (11)	0.9133 (5)	0.43186 (11)	0.0525 (6)
C1	0.38742 (14)	0.7371 (6)	0.53269 (13)	0.0535 (7)
C2	0.34907 (12)	0.5996 (5)	0.58405 (11)	0.0462 (6)
C3	0.39537 (12)	0.4079 (5)	0.61115 (11)	0.0446 (6)
C4	0.39058 (14)	0.2185 (6)	0.65685 (13)	0.0519 (7)
H4	0.3517	0.2014	0.6794	0.062*
C5	0.44415 (16)	0.0553 (6)	0.66857 (15)	0.0605 (7)
H5	0.4414	−0.0724	0.6993	0.073*
C6	0.50158 (16)	0.0802 (7)	0.63515 (17)	0.0663 (8)
H6	0.5370	−0.0327	0.6436	0.080*
C7	0.50835 (15)	0.2678 (7)	0.58932 (15)	0.0609 (8)
H7	0.5475	0.2840	0.5672	0.073*
C8	0.45450 (13)	0.4302 (6)	0.57769 (12)	0.0481 (6)
C9	0.25376 (12)	0.5309 (5)	0.64115 (12)	0.0454 (6)
C10	0.20928 (13)	0.3331 (7)	0.62764 (14)	0.0565 (7)
H10	0.2017	0.2850	0.5872	0.068*
C11	0.17563 (15)	0.2051 (7)	0.67433 (17)	0.0619 (8)
H11	0.1464	0.0673	0.6653	0.074*
C12	0.18528 (14)	0.2810 (7)	0.73385 (15)	0.0594 (8)
H12	0.1628	0.1938	0.7651	0.071*
C13	0.22774 (15)	0.4843 (6)	0.74728 (13)	0.0565 (7)
H13	0.2334	0.5381	0.7876	0.068*
C14	0.26251 (16)	0.6108 (6)	0.70102 (13)	0.0536 (7)
H14	0.2916	0.7488	0.7102	0.064*
C15	0.14226 (13)	0.8292 (7)	0.49218 (13)	0.0539 (7)
C16	0.10494 (12)	0.9666 (5)	0.44047 (11)	0.0455 (6)
C17	0.15210 (13)	1.1524 (5)	0.41286 (11)	0.0437 (6)
C18	0.14711 (14)	1.3414 (6)	0.36677 (13)	0.0528 (7)
H18	0.1080	1.3596	0.3447	0.063*
C19	0.20099 (16)	1.5019 (6)	0.35414 (15)	0.0609 (7)
H19	0.1983	1.6295	0.3235	0.073*
C20	0.25942 (17)	1.4720 (7)	0.38751 (17)	0.0661 (8)
H20	0.2955	1.5803	0.3785	0.079*
C21	0.26500 (16)	1.2858 (7)	0.43355 (16)	0.0620 (8)
H21	0.3042	1.2679	0.4555	0.074*
C22	0.21093 (13)	1.1269 (5)	0.44624 (12)	0.0472 (6)
C23	0.00927 (12)	1.0342 (6)	0.38269 (12)	0.0461 (6)
C24	0.01763 (15)	0.9423 (6)	0.32334 (14)	0.0576 (7)
H24	0.0478	0.8065	0.3154	0.069*
C25	−0.01848 (16)	1.0510 (7)	0.27619 (16)	0.0610 (8)
H25	−0.0126	0.9887	0.2365	0.073*
C26	−0.06293 (15)	1.2504 (7)	0.28746 (16)	0.0630 (8)
H26	−0.0869	1.3255	0.2555	0.076*
C27	−0.07213 (15)	1.3401 (7)	0.34652 (17)	0.0687 (9)
H27	−0.1025	1.4755	0.3541	0.082*
C28	−0.03689 (14)	1.2315 (7)	0.39430 (14)	0.0586 (7)
H28	−0.0441	1.2903	0.4341	0.070*
H1	0.4791 (10)	0.653 (6)	0.5061 (10)	0.052 (8)*
H3	0.2338 (12)	0.883 (7)	0.5172 (12)	0.064 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0687 (14)	0.0941 (18)	0.0678 (15)	0.0084 (12)	0.0068 (11)	0.0340 (13)
O2	0.0684 (14)	0.104 (2)	0.0721 (14)	−0.0040 (13)	−0.0001 (12)	0.0422 (15)
N1	0.0457 (13)	0.0711 (16)	0.0461 (12)	−0.0002 (11)	0.0104 (10)	0.0017 (12)
N2	0.0423 (12)	0.0625 (15)	0.0468 (12)	0.0047 (10)	0.0007 (9)	0.0070 (11)
N3	0.0483 (12)	0.0653 (15)	0.0470 (12)	0.0081 (11)	−0.0064 (10)	0.0028 (11)
N4	0.0419 (12)	0.0659 (15)	0.0498 (12)	0.0040 (11)	0.0037 (9)	0.0097 (11)
C1	0.0477 (15)	0.0673 (19)	0.0454 (15)	−0.0002 (13)	0.0020 (12)	0.0021 (14)
C2	0.0440 (13)	0.0533 (15)	0.0414 (12)	−0.0015 (11)	−0.0017 (10)	−0.0023 (12)
C3	0.0424 (13)	0.0466 (14)	0.0447 (13)	0.0000 (11)	−0.0018 (10)	−0.0070 (11)
C4	0.0528 (15)	0.0507 (15)	0.0523 (16)	−0.0015 (12)	−0.0007 (12)	−0.0013 (13)
C5	0.0673 (18)	0.0514 (16)	0.0628 (17)	0.0045 (14)	−0.0089 (15)	0.0015 (14)
C6	0.0586 (17)	0.0610 (18)	0.079 (2)	0.0137 (15)	−0.0129 (15)	−0.0068 (17)
C7	0.0498 (16)	0.0683 (19)	0.0645 (19)	0.0081 (13)	0.0051 (14)	−0.0094 (16)
C8	0.0452 (14)	0.0521 (15)	0.0471 (13)	0.0008 (11)	0.0006 (11)	−0.0098 (12)
C9	0.0355 (12)	0.0527 (15)	0.0479 (13)	0.0082 (11)	0.0022 (10)	0.0033 (12)
C10	0.0534 (16)	0.0620 (18)	0.0541 (16)	−0.0013 (14)	−0.0060 (14)	−0.0022 (14)
C11	0.0501 (16)	0.0592 (17)	0.076 (2)	−0.0087 (14)	−0.0041 (15)	0.0083 (16)
C12	0.0505 (17)	0.0612 (18)	0.067 (2)	0.0046 (14)	0.0100 (14)	0.0159 (15)
C13	0.0664 (17)	0.0566 (16)	0.0465 (14)	0.0090 (14)	0.0075 (13)	−0.0021 (13)
C14	0.0539 (16)	0.0525 (16)	0.0544 (16)	−0.0026 (13)	0.0024 (12)	−0.0016 (12)
C15	0.0486 (15)	0.0687 (19)	0.0444 (15)	0.0099 (14)	0.0045 (12)	0.0066 (13)
C16	0.0411 (13)	0.0532 (15)	0.0422 (13)	0.0076 (11)	0.0045 (10)	0.0025 (11)
C17	0.0444 (14)	0.0452 (14)	0.0414 (13)	0.0083 (11)	0.0055 (10)	−0.0025 (10)
C18	0.0525 (16)	0.0513 (15)	0.0545 (17)	0.0073 (12)	0.0051 (13)	0.0036 (13)
C19	0.0660 (18)	0.0527 (16)	0.0640 (17)	0.0002 (14)	0.0109 (15)	0.0083 (15)
C20	0.0609 (17)	0.0572 (18)	0.080 (2)	−0.0122 (15)	0.0092 (17)	−0.0001 (17)
C21	0.0492 (16)	0.0621 (18)	0.075 (2)	−0.0016 (13)	−0.0026 (15)	−0.0090 (17)
C22	0.0468 (14)	0.0480 (14)	0.0467 (13)	0.0062 (11)	0.0026 (11)	−0.0062 (12)
C23	0.0355 (12)	0.0510 (15)	0.0519 (14)	0.0011 (11)	0.0023 (10)	0.0069 (12)
C24	0.0606 (17)	0.0549 (17)	0.0572 (16)	0.0146 (13)	0.0025 (14)	0.0000 (14)
C25	0.0688 (19)	0.0606 (18)	0.0536 (15)	0.0011 (15)	−0.0094 (14)	−0.0036 (15)
C26	0.0542 (18)	0.0700 (19)	0.065 (2)	0.0061 (15)	−0.0105 (14)	0.0155 (16)
C27	0.0550 (18)	0.069 (2)	0.082 (2)	0.0236 (15)	0.0052 (16)	0.0144 (18)
C28	0.0542 (16)	0.0647 (19)	0.0569 (17)	0.0108 (14)	0.0077 (14)	0.0011 (14)

O1—C1	1.208 (4)	C11—H11	0.9300
O2—C15	1.211 (4)	C12—C13	1.364 (5)
N1—C1	1.350 (4)	C12—H12	0.9300
N1—C8	1.396 (4)	C13—C14	1.386 (4)
N1—H1	0.86 (1)	C13—H13	0.9300
N2—C2	1.271 (3)	C14—H14	0.9300
N2—C9	1.429 (3)	C15—C16	1.524 (4)
N3—C15	1.359 (4)	C16—C17	1.463 (4)
N3—C22	1.391 (4)	C17—C18	1.389 (4)
N3—H3	0.86 (1)	C17—C22	1.399 (4)
N4—C16	1.269 (3)	C18—C19	1.381 (4)
N4—C23	1.421 (3)	C18—H18	0.9300
C1—C2	1.529 (4)	C19—C20	1.394 (5)
C2—C3	1.466 (4)	C19—H19	0.9300
C3—C4	1.383 (4)	C20—C21	1.379 (5)
C3—C8	1.404 (4)	C20—H20	0.9300
C4—C5	1.380 (4)	C21—C22	1.380 (4)
C4—H4	0.9300	C21—H21	0.9300
C5—C6	1.375 (5)	C23—C28	1.383 (4)
C5—H5	0.9300	C23—C24	1.389 (4)
C6—C7	1.383 (5)	C24—C25	1.376 (4)
C6—H6	0.9300	C24—H24	0.9300
C7—C8	1.382 (4)	C25—C26	1.366 (4)
C7—H7	0.9300	C25—H25	0.9300
C9—C10	1.371 (4)	C26—C27	1.381 (5)
C9—C14	1.381 (4)	C26—H26	0.9300
C10—C11	1.385 (4)	C27—C28	1.377 (4)
C10—H10	0.9300	C27—H27	0.9300
C11—C12	1.371 (5)	C28—H28	0.9300
C1—N1—C8	111.9 (2)	C14—C13—H13	119.9
C1—N1—H1	126 (2)	C9—C14—C13	119.7 (3)
C8—N1—H1	121 (2)	C9—C14—H14	120.2
C2—N2—C9	118.2 (2)	C13—C14—H14	120.2
C15—N3—C22	111.4 (2)	O2—C15—N3	128.0 (3)
C15—N3—H3	121 (2)	O2—C15—C16	126.2 (3)
C22—N3—H3	128 (2)	N3—C15—C16	105.7 (2)
C16—N4—C23	120.0 (2)	N4—C16—C17	134.5 (2)
O1—C1—N1	127.9 (3)	N4—C16—C15	119.4 (2)
O1—C1—C2	126.2 (3)	C17—C16—C15	105.9 (2)
N1—C1—C2	105.8 (2)	C18—C17—C22	120.2 (3)
N2—C2—C3	135.1 (3)	C18—C17—C16	133.5 (3)
N2—C2—C1	119.0 (2)	C22—C17—C16	106.1 (2)
C3—C2—C1	105.8 (2)	C19—C18—C17	119.2 (3)
C4—C3—C8	119.4 (3)	C19—C18—H18	120.4
C4—C3—C2	134.4 (2)	C17—C18—H18	120.4
C8—C3—C2	106.1 (2)	C18—C19—C20	119.8 (3)
C5—C4—C3	119.2 (3)	C18—C19—H19	120.1
C5—C4—H4	120.4	C20—C19—H19	120.1
C3—C4—H4	120.4	C21—C20—C19	121.6 (3)
C6—C5—C4	120.4 (3)	C21—C20—H20	119.2
C6—C5—H5	119.8	C19—C20—H20	119.2
C4—C5—H5	119.8	C20—C21—C22	118.3 (3)
C5—C6—C7	122.0 (3)	C20—C21—H21	120.8
C5—C6—H6	119.0	C22—C21—H21	120.8
C7—C6—H6	119.0	C21—C22—N3	128.4 (3)
C8—C7—C6	117.3 (3)	C21—C22—C17	120.8 (3)
C8—C7—H7	121.4	N3—C22—C17	110.8 (2)
C6—C7—H7	121.4	C28—C23—C24	119.5 (3)
C7—C8—N1	128.0 (3)	C28—C23—N4	120.0 (3)
C7—C8—C3	121.6 (3)	C24—C23—N4	120.4 (3)
N1—C8—C3	110.4 (2)	C25—C24—C23	120.3 (3)
C10—C9—C14	119.9 (3)	C25—C24—H24	119.8
C10—C9—N2	119.5 (3)	C23—C24—H24	119.8
C14—C9—N2	120.5 (3)	C26—C25—C24	120.2 (3)
C9—C10—C11	119.9 (3)	C26—C25—H25	119.9
C9—C10—H10	120.1	C24—C25—H25	119.9
C11—C10—H10	120.1	C25—C26—C27	119.7 (3)
C12—C11—C10	120.1 (3)	C25—C26—H26	120.1
C12—C11—H11	119.9	C27—C26—H26	120.1
C10—C11—H11	119.9	C28—C27—C26	120.8 (3)
C13—C12—C11	120.1 (3)	C28—C27—H27	119.6
C13—C12—H12	119.9	C26—C27—H27	119.6
C11—C12—H12	119.9	C27—C28—C23	119.5 (3)
C12—C13—C14	120.2 (3)	C27—C28—H28	120.3
C12—C13—H13	119.9	C23—C28—H28	120.3
C8—N1—C1—O1	−178.4 (3)	C22—N3—C15—O2	−178.1 (3)
C8—N1—C1—C2	0.7 (3)	C22—N3—C15—C16	0.7 (3)
C9—N2—C2—C3	3.4 (5)	C23—N4—C16—C17	5.7 (5)
C9—N2—C2—C1	−179.7 (2)	C23—N4—C16—C15	−178.2 (2)
O1—C1—C2—N2	1.5 (5)	O2—C15—C16—N4	1.7 (5)
N1—C1—C2—N2	−177.6 (3)	N3—C15—C16—N4	−177.1 (3)
O1—C1—C2—C3	179.3 (3)	O2—C15—C16—C17	178.9 (3)
N1—C1—C2—C3	0.1 (3)	N3—C15—C16—C17	0.1 (3)
N2—C2—C3—C4	0.2 (6)	N4—C16—C17—C18	0.4 (5)
C1—C2—C3—C4	−177.1 (3)	C15—C16—C17—C18	−176.1 (3)
N2—C2—C3—C8	176.3 (3)	N4—C16—C17—C22	175.8 (3)
C1—C2—C3—C8	−0.9 (3)	C15—C16—C17—C22	−0.8 (3)
C8—C3—C4—C5	0.0 (4)	C22—C17—C18—C19	0.4 (4)
C2—C3—C4—C5	175.7 (3)	C16—C17—C18—C19	175.2 (3)
C3—C4—C5—C6	−0.1 (4)	C17—C18—C19—C20	0.1 (4)
C4—C5—C6—C7	0.4 (5)	C18—C19—C20—C21	−0.4 (5)
C5—C6—C7—C8	−0.6 (5)	C19—C20—C21—C22	0.0 (5)
C6—C7—C8—N1	−177.6 (3)	C20—C21—C22—N3	−177.2 (3)
C6—C7—C8—C3	0.4 (4)	C20—C21—C22—C17	0.6 (4)
C1—N1—C8—C7	176.8 (3)	C15—N3—C22—C21	176.7 (3)
C1—N1—C8—C3	−1.4 (3)	C15—N3—C22—C17	−1.2 (3)
C4—C3—C8—C7	−0.1 (4)	C18—C17—C22—C21	−0.8 (4)
C2—C3—C8—C7	−177.0 (3)	C16—C17—C22—C21	−176.9 (2)
C4—C3—C8—N1	178.2 (2)	C18—C17—C22—N3	177.3 (2)
C2—C3—C8—N1	1.4 (3)	C16—C17—C22—N3	1.2 (3)
C2—N2—C9—C10	−104.2 (3)	C16—N4—C23—C28	−107.2 (3)
C2—N2—C9—C14	78.5 (4)	C16—N4—C23—C24	77.5 (4)
C14—C9—C10—C11	−3.1 (4)	C28—C23—C24—C25	1.6 (5)
N2—C9—C10—C11	179.5 (2)	N4—C23—C24—C25	176.9 (3)
C9—C10—C11—C12	1.9 (4)	C23—C24—C25—C26	−0.1 (5)
C10—C11—C12—C13	0.5 (5)	C24—C25—C26—C27	−0.9 (5)
C11—C12—C13—C14	−1.5 (5)	C25—C26—C27—C28	0.2 (5)
C10—C9—C14—C13	2.1 (4)	C26—C27—C28—C23	1.4 (5)
N2—C9—C14—C13	179.4 (2)	C24—C23—C28—C27	−2.3 (5)
C12—C13—C14—C9	0.3 (4)	N4—C23—C28—C27	−177.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N4i	0.86 (3)	2.11 (2)	2.940 (3)	161 (3)
N3—H3···N2	0.86 (3)	2.28 (3)	3.111 (3)	164 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N4i	0.86 (3)	2.11 (2)	2.940 (3)	161 (3)
N3—H3⋯N2	0.86 (3)	2.28 (3)	3.111 (3)	164 (3)

Symmetry code: (i) .