3-(Phenyl­imino)indolin-2-one

Al Subari, A.; Bouhfid, R.; Zouihri, H.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S160053681000259X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o453

https://doi.org/10.1107/S160053681000259X

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3-(Phenylimino)indolin-2-one

Abdusalam Al Subari,^a Rachid Bouhfid,^b Hafid Zouihri,^c El Mokhtar Essassi ^a and Seik Weng Ng ^d ^*

^aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, ^bInstitute of Nanomaterials and Nanotechnology, Avenue de l'Armée Royale, Madinat El Irfane, 10100 Rabat, Morocco, ^cCNRST Division of UATRS Angle Allal Fassi/FAR, BP 8027 Hay Riad, 10000 Rabat, Morocco, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 20 January 2010; accepted 20 January 2010; online 27 January 2010)

The imino C=N double bond in the title compound, C₁₄H₁₀N₂O, exists in an E conformation, with the phenyl ring being twisted by 80.7 (1)° in one independent molecule and by 81.4 (1)° in the other with respect to the plane of the indoline fused-ring system. The two independent molecules 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_r = 222.24
Orthorhombic, P n a 2₁
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.118
S = 1.10
2619 reflections
315 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻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) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ .

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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681000259X/bt5177Isup2.hkl

checkCIF report

Related literature top

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 top

The compound was synthesized from the reaction of isatin and aniline in ethanol according to a literature method (Grimshaw & Begley, 1974), and crystals were obtained by recrystallization from ethanol.

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the two independent molecules of C₁₄H₁₀N₂O at the 50% probability level; hydrogen atoms are drawn as spheres of an arbitrary radius.

3-(Phenylimino)indolin-2-one top

Crystal data top

C₁₄H₁₀N₂O	F(000) = 928
M_r = 222.24	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0745P)² + 0.0171P] where P = (F_o² + 2F_c²)/3
2619 reflections	(Δ/σ)_max = 0.001
315 parameters	Δρ_max = 0.19 e Å⁻³
3 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₄H₁₀N₂O	V = 2215.77 (8) Å³
M_r = 222.24	Z = 8
Orthorhombic, Pna2₁	Mo Kα radiation
a = 20.1647 (4) Å	µ = 0.09 mm⁻¹
b = 5.0223 (1) Å	T = 293 K
c = 21.8791 (5) Å	0.3 × 0.3 × 0.3 mm

Data collection top

Bruker APEXII diffractometer	2042 reflections with I > 2σ(I)
15055 measured reflections	R_int = 0.030
2619 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	3 restraints
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.19 e Å⁻³
2619 reflections	Δρ_min = −0.20 e Å⁻³
315 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+3/2, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀N₂O
M_r	222.24
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	20.1647 (4), 5.0223 (1), 21.8791 (5)
V (Å³)	2215.77 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.3 × 0.3 × 0.3

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15055, 2619, 2042
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.118, 1.10
No. of reflections	2619
No. of parameters	315
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+3/2, z.

Acknowledgements

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

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