4-{(E)-[2-(4-Iodo-but-oxy)benzyl-idene]amino}-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one.

The title Schiff base compound, C(22)H(24)IN(3)O(2), adopts an E configuration about the central C=N bond. The pyrazolone ring makes a dihedral angle of 49.68 (10)° with its attached phenyl ring. The phenolate plane makes dihedral angles of 16.78 (9) and 50.54 (9)°, respectively, with the pyrazolone ring and the terminal phenyl ring. An intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal structure, an inter-molecular C-H⋯O hydrogen bond is also observed.

Related literature

For background to and applications of Schiff bases, see: Tarafder et al. (2002 ▶); Silver & Soderlund (2005 ▶); Vicini et al. (2003 ▶); Ozdemir et al. (2007 ▶); Joshi et al. (2004 ▶). For background to and the biological activity of 4-amino­anti­pyrene and its derivatives, see: Jain et al. (2003 ▶); Filho et al. (1998 ▶); Sondhi et al. (1999 ▶); Mishra (1999 ▶); Sondhi et al. (2001 ▶). For related structures, see: Eryigit & Kendi (1998 ▶); Manikandan et al. (2000 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C22H24IN3O2

M = 489.34

Monoclinic,

a = 11.5235 (10) Å

b = 16.4156 (14) Å

c = 11.2828 (9) Å

β = 94.010 (2)°

V = 2129.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.53 mm−1

T = 100 K

0.41 × 0.34 × 0.29 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.571, T max = 0.663

36214 measured reflections

9632 independent reflections

7935 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.159

S = 1.05

9632 reflections

255 parameters

H-atom parameters constrained

Δρmax = 1.26 e Å−3

Δρmin = −1.68 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020374/is2554sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020374/is2554Isup2.hkl

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

C22H24IN3O2	F(000) = 984
Mr = 489.34	Dx = 1.527 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9944 reflections
a = 11.5235 (10) Å	θ = 2.7–35.4°
b = 16.4156 (14) Å	µ = 1.53 mm−1
c = 11.2828 (9) Å	T = 100 K
β = 94.010 (2)°	Blcok, yellow
V = 2129.1 (3) Å3	0.41 × 0.34 × 0.29 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	9632 independent reflections
Radiation source: fine-focus sealed tube	7935 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 35.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→18
Tmin = 0.571, Tmax = 0.663	k = −26→26
36214 measured reflections	l = −17→18

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1027P)2 + 1.5532P] where P = (Fo2 + 2Fc2)/3
9632 reflections	(Δ/σ)max = 0.001
255 parameters	Δρmax = 1.26 e Å−3
0 restraints	Δρmin = −1.68 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
I1	0.290561 (14)	0.362436 (10)	0.802978 (17)	0.03475 (7)
O1	0.68399 (13)	0.05872 (8)	0.94462 (12)	0.0192 (2)
O2	0.71122 (14)	0.22745 (9)	0.66181 (13)	0.0206 (2)
N1	0.76696 (14)	−0.05557 (10)	1.03829 (14)	0.0182 (3)
N2	0.87138 (14)	−0.09878 (10)	1.03161 (15)	0.0200 (3)
N3	0.89080 (14)	0.03071 (9)	0.78003 (13)	0.0163 (2)
C1	0.78638 (19)	−0.05051 (15)	1.25448 (18)	0.0266 (4)
H1A	0.8669	−0.0531	1.2531	0.032*
C2	0.7339 (2)	−0.04626 (17)	1.36239 (19)	0.0315 (5)
H2A	0.7798	−0.0461	1.4336	0.038*
C3	0.6135 (2)	−0.04230 (14)	1.3637 (2)	0.0275 (4)
H3A	0.5791	−0.0395	1.4357	0.033*
C4	0.54450 (18)	−0.04253 (12)	1.25739 (19)	0.0232 (3)
H4A	0.4640	−0.0392	1.2586	0.028*
C5	0.59526 (17)	−0.04769 (11)	1.14967 (18)	0.0199 (3)
H5A	0.5492	−0.0490	1.0786	0.024*
C6	0.71592 (17)	−0.05082 (11)	1.14923 (16)	0.0186 (3)
C7	0.92082 (16)	−0.07340 (11)	0.93152 (15)	0.0172 (3)
C8	0.85924 (15)	−0.00877 (10)	0.88180 (15)	0.0156 (3)
C9	0.75980 (16)	0.00540 (10)	0.95158 (15)	0.0161 (3)
C10	0.82737 (16)	0.09014 (10)	0.73798 (15)	0.0166 (3)
H10A	0.7665	0.1092	0.7803	0.020*
C11	0.85006 (16)	0.12799 (10)	0.62451 (15)	0.0160 (3)
C12	0.93106 (16)	0.09552 (11)	0.55089 (16)	0.0184 (3)
H12A	0.9768	0.0516	0.5775	0.022*
C13	0.94457 (18)	0.12744 (12)	0.43891 (17)	0.0209 (3)
H13A	0.9995	0.1057	0.3912	0.025*
C14	0.87488 (18)	0.19228 (12)	0.39885 (16)	0.0210 (3)
H14A	0.8814	0.2124	0.3226	0.025*
C15	0.79573 (17)	0.22751 (11)	0.47051 (16)	0.0195 (3)
H15A	0.7510	0.2717	0.4432	0.023*
C16	0.78371 (16)	0.19599 (10)	0.58414 (15)	0.0167 (3)
C17	0.64112 (18)	0.29607 (12)	0.62471 (18)	0.0224 (3)
H17A	0.5886	0.2813	0.5572	0.027*
H17B	0.6902	0.3403	0.6010	0.027*
C18	0.57265 (18)	0.32256 (11)	0.72692 (19)	0.0229 (3)
H18A	0.5220	0.3673	0.7010	0.027*
H18B	0.6262	0.3426	0.7905	0.027*
C19	0.49946 (19)	0.25498 (12)	0.7752 (2)	0.0244 (3)
H19A	0.4505	0.2319	0.7103	0.029*
H19B	0.5506	0.2122	0.8072	0.029*
C20	0.4233 (2)	0.28321 (15)	0.8710 (2)	0.0301 (4)
H20A	0.4709	0.3111	0.9327	0.036*
H20B	0.3884	0.2362	0.9066	0.036*
C21	0.8675 (2)	−0.18482 (14)	1.0635 (2)	0.0313 (5)
H21A	0.9438	−0.2080	1.0613	0.047*
H21B	0.8147	−0.2129	1.0080	0.047*
H21C	0.8414	−0.1902	1.1421	0.047*
C22	1.02298 (18)	−0.11555 (13)	0.88815 (18)	0.0223 (3)
H22A	1.0828	−0.1196	0.9515	0.033*
H22B	1.0517	−0.0852	0.8236	0.033*
H22C	1.0008	−0.1692	0.8612	0.033*

	U11	U22	U33	U12	U13	U23
I1	0.02522 (9)	0.03191 (10)	0.04766 (12)	0.00818 (5)	0.00638 (7)	0.01372 (6)
O1	0.0219 (6)	0.0172 (5)	0.0185 (5)	0.0063 (4)	0.0021 (4)	0.0012 (4)
O2	0.0269 (7)	0.0163 (5)	0.0188 (5)	0.0067 (5)	0.0033 (5)	0.0036 (4)
N1	0.0186 (6)	0.0191 (6)	0.0169 (6)	0.0048 (5)	0.0018 (5)	0.0040 (5)
N2	0.0181 (6)	0.0195 (6)	0.0224 (7)	0.0051 (5)	0.0023 (5)	0.0069 (5)
N3	0.0184 (6)	0.0155 (6)	0.0147 (6)	0.0014 (5)	−0.0003 (4)	0.0013 (4)
C1	0.0213 (8)	0.0392 (11)	0.0191 (8)	−0.0067 (7)	0.0002 (6)	0.0047 (7)
C2	0.0296 (10)	0.0457 (13)	0.0192 (8)	−0.0092 (9)	0.0020 (7)	0.0032 (8)
C3	0.0321 (10)	0.0283 (9)	0.0232 (8)	−0.0054 (8)	0.0091 (7)	−0.0004 (7)
C4	0.0233 (8)	0.0184 (7)	0.0288 (9)	0.0010 (6)	0.0076 (7)	0.0021 (6)
C5	0.0197 (7)	0.0165 (7)	0.0234 (8)	0.0014 (5)	0.0012 (6)	0.0012 (6)
C6	0.0200 (7)	0.0182 (7)	0.0177 (7)	−0.0004 (5)	0.0020 (5)	0.0031 (5)
C7	0.0181 (7)	0.0169 (6)	0.0162 (6)	0.0029 (5)	−0.0003 (5)	0.0028 (5)
C8	0.0174 (6)	0.0146 (6)	0.0145 (6)	0.0020 (5)	−0.0001 (5)	0.0010 (5)
C9	0.0190 (7)	0.0143 (6)	0.0149 (6)	0.0017 (5)	−0.0002 (5)	0.0008 (5)
C10	0.0206 (7)	0.0139 (6)	0.0151 (6)	0.0016 (5)	0.0005 (5)	0.0006 (5)
C11	0.0187 (7)	0.0137 (6)	0.0153 (6)	−0.0002 (5)	−0.0008 (5)	0.0002 (5)
C12	0.0204 (7)	0.0184 (7)	0.0162 (6)	0.0021 (6)	−0.0001 (5)	−0.0001 (5)
C13	0.0223 (8)	0.0235 (8)	0.0169 (7)	−0.0005 (6)	0.0027 (6)	0.0009 (6)
C14	0.0227 (8)	0.0232 (8)	0.0169 (7)	−0.0017 (6)	0.0007 (6)	0.0042 (6)
C15	0.0209 (7)	0.0187 (7)	0.0186 (7)	−0.0012 (6)	−0.0009 (6)	0.0050 (5)
C16	0.0199 (7)	0.0138 (6)	0.0162 (6)	−0.0010 (5)	−0.0001 (5)	0.0006 (5)
C17	0.0257 (8)	0.0170 (7)	0.0245 (8)	0.0053 (6)	0.0026 (6)	0.0055 (6)
C18	0.0246 (8)	0.0137 (6)	0.0304 (9)	0.0020 (6)	0.0024 (7)	0.0009 (6)
C19	0.0252 (8)	0.0172 (7)	0.0310 (9)	0.0018 (6)	0.0025 (7)	0.0036 (6)
C20	0.0298 (10)	0.0298 (10)	0.0314 (10)	0.0106 (8)	0.0063 (8)	0.0122 (8)
C21	0.0305 (10)	0.0227 (9)	0.0418 (12)	0.0084 (8)	0.0110 (9)	0.0154 (8)
C22	0.0210 (8)	0.0219 (7)	0.0243 (8)	0.0062 (6)	0.0031 (6)	0.0024 (6)

I1—C20	2.111 (2)	C11—C12	1.398 (3)
O1—C9	1.235 (2)	C11—C16	1.410 (2)
O2—C16	1.355 (2)	C12—C13	1.387 (3)
O2—C17	1.432 (2)	C12—H12A	0.9300
N1—C9	1.398 (2)	C13—C14	1.390 (3)
N1—N2	1.403 (2)	C13—H13A	0.9300
N1—C6	1.422 (2)	C14—C15	1.387 (3)
N2—C7	1.365 (2)	C14—H14A	0.9300
N2—C21	1.459 (3)	C15—C16	1.398 (2)
N3—C10	1.289 (2)	C15—H15A	0.9300
N3—C8	1.389 (2)	C17—C18	1.506 (3)
C1—C6	1.391 (3)	C17—H17A	0.9700
C1—C2	1.398 (3)	C17—H17B	0.9700
C1—H1A	0.9300	C18—C19	1.518 (3)
C2—C3	1.390 (3)	C18—H18A	0.9700
C2—H2A	0.9300	C18—H18B	0.9700
C3—C4	1.392 (3)	C19—C20	1.512 (3)
C3—H3A	0.9300	C19—H19A	0.9700
C4—C5	1.388 (3)	C19—H19B	0.9700
C4—H4A	0.9300	C20—H20A	0.9700
C5—C6	1.392 (3)	C20—H20B	0.9700
C5—H5A	0.9300	C21—H21A	0.9600
C7—C8	1.374 (2)	C21—H21B	0.9600
C7—C22	1.478 (3)	C21—H21C	0.9600
C8—C9	1.454 (2)	C22—H22A	0.9600
C10—C11	1.463 (2)	C22—H22B	0.9600
C10—H10A	0.9300	C22—H22C	0.9600
C16—O2—C17	118.14 (15)	C14—C13—H13A	120.4
C9—N1—N2	109.46 (14)	C15—C14—C13	121.23 (17)
C9—N1—C6	124.67 (15)	C15—C14—H14A	119.4
N2—N1—C6	118.95 (15)	C13—C14—H14A	119.4
C7—N2—N1	107.41 (14)	C14—C15—C16	119.45 (17)
C7—N2—C21	121.40 (17)	C14—C15—H15A	120.3
N1—N2—C21	115.78 (16)	C16—C15—H15A	120.3
C10—N3—C8	118.86 (15)	O2—C16—C15	123.87 (16)
C6—C1—C2	118.8 (2)	O2—C16—C11	115.96 (15)
C6—C1—H1A	120.6	C15—C16—C11	120.17 (17)
C2—C1—H1A	120.6	O2—C17—C18	108.56 (15)
C3—C2—C1	120.3 (2)	O2—C17—H17A	110.0
C3—C2—H2A	119.9	C18—C17—H17A	110.0
C1—C2—H2A	119.9	O2—C17—H17B	110.0
C2—C3—C4	120.08 (19)	C18—C17—H17B	110.0
C2—C3—H3A	120.0	H17A—C17—H17B	108.4
C4—C3—H3A	120.0	C17—C18—C19	113.44 (16)
C5—C4—C3	120.3 (2)	C17—C18—H18A	108.9
C5—C4—H4A	119.9	C19—C18—H18A	108.9
C3—C4—H4A	119.9	C17—C18—H18B	108.9
C4—C5—C6	119.19 (18)	C19—C18—H18B	108.9
C4—C5—H5A	120.4	H18A—C18—H18B	107.7
C6—C5—H5A	120.4	C20—C19—C18	113.41 (18)
C1—C6—C5	121.36 (18)	C20—C19—H19A	108.9
C1—C6—N1	119.94 (18)	C18—C19—H19A	108.9
C5—C6—N1	118.69 (17)	C20—C19—H19B	108.9
N2—C7—C8	109.87 (15)	C18—C19—H19B	108.9
N2—C7—C22	121.27 (16)	H19A—C19—H19B	107.7
C8—C7—C22	128.82 (16)	C19—C20—I1	111.76 (15)
C7—C8—N3	122.69 (16)	C19—C20—H20A	109.3
C7—C8—C9	107.86 (15)	I1—C20—H20A	109.3
N3—C8—C9	129.42 (15)	C19—C20—H20B	109.3
O1—C9—N1	123.96 (16)	I1—C20—H20B	109.3
O1—C9—C8	131.28 (16)	H20A—C20—H20B	107.9
N1—C9—C8	104.73 (14)	N2—C21—H21A	109.5
N3—C10—C11	120.79 (16)	N2—C21—H21B	109.5
N3—C10—H10A	119.6	H21A—C21—H21B	109.5
C11—C10—H10A	119.6	N2—C21—H21C	109.5
C12—C11—C16	118.64 (16)	H21A—C21—H21C	109.5
C12—C11—C10	121.71 (16)	H21B—C21—H21C	109.5
C16—C11—C10	119.52 (16)	C7—C22—H22A	109.5
C13—C12—C11	121.30 (17)	C7—C22—H22B	109.5
C13—C12—H12A	119.3	H22A—C22—H22B	109.5
C11—C12—H12A	119.3	C7—C22—H22C	109.5
C12—C13—C14	119.12 (18)	H22A—C22—H22C	109.5
C12—C13—H13A	120.4	H22B—C22—H22C	109.5
C9—N1—N2—C7	−8.6 (2)	C6—N1—C9—O1	−21.4 (3)
C6—N1—N2—C7	−160.89 (17)	N2—N1—C9—C8	6.5 (2)
C9—N1—N2—C21	−147.91 (19)	C6—N1—C9—C8	156.82 (17)
C6—N1—N2—C21	59.8 (2)	C7—C8—C9—O1	175.93 (19)
C6—C1—C2—C3	−0.1 (4)	N3—C8—C9—O1	−6.2 (3)
C1—C2—C3—C4	0.0 (4)	C7—C8—C9—N1	−2.11 (19)
C2—C3—C4—C5	0.8 (3)	N3—C8—C9—N1	175.74 (17)
C3—C4—C5—C6	−1.4 (3)	C8—N3—C10—C11	−173.62 (16)
C2—C1—C6—C5	−0.5 (3)	N3—C10—C11—C12	7.8 (3)
C2—C1—C6—N1	−179.6 (2)	N3—C10—C11—C16	−176.25 (17)
C4—C5—C6—C1	1.3 (3)	C16—C11—C12—C13	−1.8 (3)
C4—C5—C6—N1	−179.60 (17)	C10—C11—C12—C13	174.17 (18)
C9—N1—C6—C1	−116.1 (2)	C11—C12—C13—C14	−0.9 (3)
N2—N1—C6—C1	31.7 (3)	C12—C13—C14—C15	2.6 (3)
C9—N1—C6—C5	64.8 (3)	C13—C14—C15—C16	−1.6 (3)
N2—N1—C6—C5	−147.45 (18)	C17—O2—C16—C15	1.2 (3)
N1—N2—C7—C8	7.2 (2)	C17—O2—C16—C11	−179.42 (17)
C21—N2—C7—C8	143.72 (19)	C14—C15—C16—O2	178.16 (18)
N1—N2—C7—C22	−170.71 (17)	C14—C15—C16—C11	−1.2 (3)
C21—N2—C7—C22	−34.2 (3)	C12—C11—C16—O2	−176.58 (16)
N2—C7—C8—N3	178.79 (16)	C10—C11—C16—O2	7.4 (2)
C22—C7—C8—N3	−3.5 (3)	C12—C11—C16—C15	2.8 (3)
N2—C7—C8—C9	−3.2 (2)	C10—C11—C16—C15	−173.23 (17)
C22—C7—C8—C9	174.55 (19)	C16—O2—C17—C18	−177.32 (16)
C10—N3—C8—C7	178.99 (17)	O2—C17—C18—C19	−55.7 (2)
C10—N3—C8—C9	1.4 (3)	C17—C18—C19—C20	−175.30 (18)
N2—N1—C9—O1	−171.71 (17)	C18—C19—C20—I1	67.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O1	0.93	2.30	2.995 (2)	132
C17—H17B···O1i	0.97	2.42	3.193 (2)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O1	0.93	2.30	2.995 (2)	132
C17—H17B⋯O1i	0.97	2.42	3.193 (2)	137

Symmetry code: (i) .