(E)-4-[(4-Bromo­benzyl­idene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

The title compound, C₁₈H₁₆BrN₃O, presents the expected mol­ecular geometry. There are π–π inter­actions between neighbouring mol­ecules, through the imine functionality, forming dimers in the crystal structure. Weak C—H...O inter­actions link the dimers, forming a chain structure.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C)= 0.005 Å
• R factor = 0.051
• wR factor = 0.113
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(E)-4-[(4-Bromobenzylidene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Crystal data

C18H16BrN3O	F(000) = 1504
Mr = 370.25	Dx = 1.493 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3812 reflections
a = 6.9803 (4) Å	θ = 2.1–25.4°
b = 17.5191 (9) Å	µ = 2.50 mm^−1
c = 26.9377 (14) Å	T = 291 K
V = 3294.2 (3) Å^3	Block, yellow
Z = 8	0.32 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3241 independent reflections
Radiation source: sealed tube	2307 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
φ and ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
Tmin = 0.460, Tmax = 0.550	k = −21→21
19952 measured reflections	l = −33→33

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.05P)^2 + 1.88P] where P = (Fo^2 + 2Fc^2)/3
3241 reflections	(Δ/σ)max < 0.001
210 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.5658 (6)	0.7643 (2)	0.65022 (14)	0.0380 (9)
C2	0.5504 (6)	0.6850 (2)	0.65020 (14)	0.0435 (10)
H2	0.4751	0.6607	0.6265	0.052*
C3	0.6478 (6)	0.6423 (2)	0.68558 (15)	0.0433 (9)
H3	0.6376	0.5894	0.6856	0.052*
C4	0.7604 (6)	0.6787 (2)	0.72102 (16)	0.0467 (10)
H4	0.8250	0.6501	0.7448	0.056*
C5	0.7762 (6)	0.7576 (2)	0.72087 (15)	0.0456 (9)
H5	0.8520	0.7818	0.7445	0.055*
C6	0.6793 (6)	0.8007 (3)	0.68551 (15)	0.0458 (10)
H6	0.6902	0.8536	0.6855	0.055*
C7	0.5741 (6)	0.8537 (2)	0.57949 (14)	0.0363 (8)
C8	0.4456 (6)	0.8586 (2)	0.53658 (14)	0.0424 (9)
C9	0.2862 (5)	0.8182 (2)	0.54792 (13)	0.0364 (8)
C10	0.6380 (6)	0.9253 (2)	0.48153 (15)	0.0437 (9)
H10	0.7260	0.9315	0.5071	0.052*
C11	0.6804 (5)	0.9534 (2)	0.43779 (14)	0.0389 (8)
C12	0.8582 (6)	0.9871 (2)	0.42999 (15)	0.0419 (9)
H12	0.9460	0.9904	0.4559	0.050*
C13	0.9045 (5)	1.0159 (2)	0.38349 (14)	0.0390 (9)
H13	1.0231	1.0387	0.3783	0.047*
C14	0.7742 (6)	1.0107 (2)	0.34478 (14)	0.0428 (10)
C15	0.5964 (6)	0.9767 (2)	0.35242 (15)	0.0392 (9)
H15	0.5091	0.9731	0.3264	0.047*
C16	0.5497 (5)	0.9481 (2)	0.39907 (13)	0.0370 (8)
H16	0.4309	0.9254	0.4043	0.044*
C17	0.1385 (6)	0.7684 (2)	0.62533 (14)	0.0411 (9)
H17A	0.0848	0.8157	0.6367	0.062*
H17B	0.1826	0.7393	0.6533	0.062*
H17C	0.0424	0.7398	0.6078	0.062*
C18	0.1081 (6)	0.8101 (2)	0.51640 (15)	0.0451 (10)
H18A	0.0819	0.7570	0.5109	0.068*
H18B	0.1278	0.8350	0.4851	0.068*
H18C	0.0015	0.8332	0.5332	0.068*
Br1	0.83900 (7)	1.04881 (3)	0.280562 (16)	0.05384 (16)
N1	0.4729 (5)	0.81047 (18)	0.61548 (11)	0.0408 (8)
N2	0.2996 (4)	0.78398 (17)	0.59204 (11)	0.0362 (7)
N3	0.4820 (5)	0.88983 (18)	0.49082 (11)	0.0413 (8)
O1	0.7378 (4)	0.87729 (16)	0.58694 (10)	0.0445 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.035 (2)	0.038 (2)	0.040 (2)	0.0016 (16)	0.0059 (17)	−0.0052 (16)
C2	0.042 (3)	0.050 (2)	0.038 (2)	0.0017 (19)	−0.0068 (17)	−0.0125 (18)
C3	0.032 (2)	0.045 (2)	0.054 (2)	0.0140 (19)	0.0033 (18)	−0.0006 (17)
C4	0.041 (2)	0.042 (2)	0.058 (2)	0.0068 (19)	−0.010 (2)	0.0040 (19)
C5	0.041 (2)	0.049 (2)	0.047 (2)	−0.0087 (18)	0.0008 (19)	−0.0047 (19)
C6	0.034 (2)	0.057 (3)	0.047 (2)	−0.0109 (19)	−0.0026 (17)	−0.0036 (18)
C7	0.039 (2)	0.0261 (18)	0.043 (2)	−0.0021 (16)	0.0008 (17)	0.0004 (15)
C8	0.040 (2)	0.047 (2)	0.040 (2)	−0.0017 (18)	0.0009 (17)	−0.0099 (18)
C9	0.035 (2)	0.046 (2)	0.0288 (18)	0.0010 (17)	−0.0060 (15)	−0.0091 (15)
C10	0.044 (3)	0.044 (2)	0.043 (2)	0.004 (2)	−0.0034 (19)	−0.0074 (17)
C11	0.030 (2)	0.0382 (19)	0.048 (2)	0.0016 (18)	−0.0089 (16)	−0.0122 (18)
C12	0.030 (2)	0.042 (2)	0.054 (2)	−0.0048 (17)	−0.0065 (18)	−0.0093 (18)
C13	0.026 (2)	0.040 (2)	0.051 (2)	−0.0140 (16)	0.0082 (16)	−0.0117 (17)
C14	0.049 (3)	0.041 (2)	0.0383 (19)	−0.0156 (18)	−0.0076 (17)	−0.0024 (16)
C15	0.031 (2)	0.044 (2)	0.042 (2)	−0.0122 (17)	−0.0126 (15)	0.0105 (17)
C16	0.030 (2)	0.037 (2)	0.045 (2)	−0.0096 (16)	−0.0119 (16)	0.0024 (16)
C17	0.039 (2)	0.042 (2)	0.0424 (19)	−0.0105 (18)	0.0110 (18)	0.0105 (16)
C18	0.045 (3)	0.048 (2)	0.043 (2)	−0.0088 (19)	−0.0126 (17)	−0.0018 (17)
Br1	0.0536 (3)	0.0537 (3)	0.0542 (3)	0.0104 (2)	0.0105 (2)	0.0134 (2)
N1	0.041 (2)	0.0386 (18)	0.0427 (18)	−0.0135 (15)	−0.0047 (15)	−0.0019 (14)
N2	0.0347 (18)	0.0332 (16)	0.0407 (17)	−0.0127 (14)	0.0013 (13)	−0.0086 (13)
N3	0.045 (2)	0.0414 (19)	0.0374 (17)	−0.0040 (16)	−0.0006 (15)	−0.0038 (13)
O1	0.0431 (16)	0.0418 (15)	0.0487 (16)	−0.0141 (13)	−0.0044 (13)	0.0043 (12)

Geometric parameters (Å, º)

C1—C6	1.392 (5)	C10—H10	0.9300
C1—C2	1.393 (6)	C11—C16	1.389 (5)
C1—N1	1.396 (5)	C11—C12	1.391 (5)
C2—C3	1.390 (6)	C12—C13	1.388 (6)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.391 (6)	C13—C14	1.387 (5)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.387 (6)	C14—C15	1.392 (6)
C4—H4	0.9300	C14—Br1	1.909 (4)
C5—C6	1.391 (6)	C15—C16	1.392 (5)
C5—H5	0.9300	C15—H15	0.9300
C6—H6	0.9300	C16—H16	0.9300
C7—O1	1.232 (5)	C17—N2	1.464 (5)
C7—N1	1.418 (5)	C17—H17A	0.9600
C7—C8	1.466 (5)	C17—H17B	0.9600
C8—C9	1.353 (6)	C17—H17C	0.9600
C8—N3	1.372 (5)	C18—H18A	0.9600
C9—N2	1.334 (5)	C18—H18B	0.9600
C9—C18	1.512 (5)	C18—H18C	0.9600
C10—N3	1.278 (5)	N1—N2	1.442 (4)
C10—C11	1.311 (6)
C6—C1—C2	120.1 (4)	C13—C12—H12	120.1
C6—C1—N1	117.2 (3)	C11—C12—H12	120.1
C2—C1—N1	122.8 (4)	C14—C13—C12	120.2 (4)
C3—C2—C1	120.0 (4)	C14—C13—H13	119.9
C3—C2—H2	120.0	C12—C13—H13	119.9
C1—C2—H2	120.0	C13—C14—C15	120.1 (4)
C2—C3—C4	120.0 (4)	C13—C14—Br1	120.2 (3)
C2—C3—H3	120.0	C15—C14—Br1	119.7 (3)
C4—C3—H3	120.0	C16—C15—C14	119.8 (3)
C5—C4—C3	120.0 (4)	C16—C15—H15	120.1
C5—C4—H4	120.0	C14—C15—H15	120.1
C3—C4—H4	120.0	C11—C16—C15	120.0 (3)
C4—C5—C6	120.3 (4)	C11—C16—H16	120.0
C4—C5—H5	119.9	C15—C16—H16	120.0
C6—C5—H5	119.9	N2—C17—H17A	109.5
C5—C6—C1	119.7 (4)	N2—C17—H17B	109.5
C5—C6—H6	120.1	H17A—C17—H17B	109.5
C1—C6—H6	120.1	N2—C17—H17C	109.5
O1—C7—N1	122.0 (3)	H17A—C17—H17C	109.5
O1—C7—C8	132.6 (4)	H17B—C17—H17C	109.5
N1—C7—C8	105.4 (3)	C9—C18—H18A	109.5
C9—C8—N3	124.3 (4)	C9—C18—H18B	109.5
C9—C8—C7	107.1 (3)	H18A—C18—H18B	109.5
N3—C8—C7	128.2 (4)	C9—C18—H18C	109.5
N2—C9—C8	112.2 (3)	H18A—C18—H18C	109.5
N2—C9—C18	121.0 (4)	H18B—C18—H18C	109.5
C8—C9—C18	126.7 (4)	C1—N1—C7	122.4 (3)
N3—C10—C11	123.4 (4)	C1—N1—N2	119.8 (3)
N3—C10—H10	118.3	C7—N1—N2	106.9 (3)
C11—C10—H10	118.3	C9—N2—N1	107.7 (3)
C10—C11—C16	120.1 (4)	C9—N2—C17	125.2 (3)
C10—C11—C12	119.8 (4)	N1—N2—C17	115.9 (3)
C16—C11—C12	120.1 (4)	C10—N3—C8	121.8 (4)
C13—C12—C11	119.9 (4)