4-[(Z)-(2-Fluorenyl­amino)­phenyl­methyl­ene]-5-methyl-2-phenyl-2H-pyrazol-3(4H)-one

The NH unit on the exocyclic C=C double bond in the title compound, C₃₀H₂₃N₃O, lies on the same side of the double bond as the carbonyl unit of the pyrazolonyl ring, and the two interact through an N—H...O hydrogen bond [2.671 (2) Å].

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.116
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

4-[(Z)-(2-Fluorenylamino)phenylmethylene]-5-methyl-2-phenyl-2H-pyrazol-3(4H)-one

Crystal data

C30H23N3O	F(000) = 928
Mr = 441.51	Dx = 1.270 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 934 reflections
a = 9.700 (1) Å	θ = 2.9–25.7°
b = 22.441 (3) Å	µ = 0.08 mm^−1
c = 10.638 (1) Å	T = 298 K
β = 94.583 (3)°	Block, colorless
V = 2308.4 (5) Å^3	0.37 × 0.30 × 0.23 mm
Z = 4

Data collection

Bruker SMART area-detector diffractometer	2835 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
Graphite monochromator	θmax = 27.0°, θmin = 1.8°
φ and ω scans	h = −12→10
13811 measured reflections	k = −28→28
5038 independent reflections	l = −11→13

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.05P)^2 + 0.2453P] where P = (Fo^2 + 2Fc^2)/3
5038 reflections	(Δ/σ)max = 0.001
312 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

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

	x	y	z	Uiso*/Ueq
O1	0.7523 (1)	0.5340 (1)	0.4559 (1)	0.0539 (4)
N1	0.7520 (1)	0.6209 (1)	0.5774 (1)	0.0432 (4)
N2	0.6619 (2)	0.6688 (1)	0.5936 (1)	0.0463 (4)
N3	0.5141 (2)	0.5244 (1)	0.3130 (1)	0.0474 (4)
C1	0.8671 (2)	0.6126 (1)	0.6669 (2)	0.0427 (4)
C2	0.9736 (2)	0.5743 (1)	0.6417 (2)	0.0584 (5)
C3	1.0814 (2)	0.5652 (1)	0.7325 (2)	0.0721 (6)
C4	1.0853 (2)	0.5937 (1)	0.8466 (2)	0.0710 (7)
C5	0.9805 (2)	0.6323 (1)	0.8701 (2)	0.0630 (6)
C6	0.8718 (2)	0.6423 (1)	0.7811 (2)	0.0520 (5)
C7	0.6966 (2)	0.5812 (1)	0.4889 (2)	0.0414 (4)
C8	0.5643 (2)	0.6060 (1)	0.4452 (2)	0.0393 (4)
C9	0.5531 (2)	0.6599 (1)	0.5151 (2)	0.0422 (4)
C10	0.4381 (2)	0.7044 (1)	0.5115 (2)	0.0640 (6)
C11	0.4747 (2)	0.5775 (1)	0.3549 (2)	0.0401 (4)
C12	0.3401 (2)	0.6041 (1)	0.3089 (2)	0.0397 (4)
C13	0.3373 (2)	0.6552 (1)	0.2357 (2)	0.0460 (4)
C14	0.2127 (2)	0.6810 (1)	0.1943 (2)	0.0556 (5)
C15	0.0915 (2)	0.6563 (1)	0.2264 (2)	0.0638 (6)
C16	0.0934 (2)	0.6057 (1)	0.2995 (2)	0.0718 (6)
C17	0.2171 (2)	0.5793 (1)	0.3407 (2)	0.0572 (5)
C18	0.3780 (2)	0.4056 (1)	0.0268 (2)	0.0432 (4)
C19	0.3271 (2)	0.4632 (1)	0.0208 (2)	0.0511 (5)
C20	0.3675 (2)	0.5032 (1)	0.1147 (2)	0.0510 (5)
C21	0.4585 (2)	0.4860 (1)	0.2160 (2)	0.0437 (4)
C22	0.5092 (2)	0.4280 (1)	0.2226 (2)	0.0439 (4)
C23	0.4685 (2)	0.3879 (1)	0.1281 (2)	0.0447 (4)
C24	0.3548 (2)	0.3545 (1)	−0.0589 (2)	0.0447 (4)
C25	0.2807 (2)	0.3497 (1)	−0.1752 (2)	0.0541 (5)
C26	0.2802 (2)	0.2953 (1)	−0.2379 (2)	0.0634 (6)
C27	0.3507 (2)	0.2470 (1)	−0.1846 (2)	0.0649 (6)
C28	0.4249 (2)	0.2518 (1)	−0.0688 (2)	0.0607 (5)
C29	0.4280 (2)	0.3055 (1)	−0.0066 (2)	0.0488 (5)
C30	0.5056 (2)	0.3233 (1)	0.1164 (2)	0.0554 (5)
H3n	0.604 (2)	0.5129 (8)	0.354 (2)	0.076 (6)*
H2	0.9725	0.5549	0.5643	0.070*
H3	1.1525	0.5392	0.7160	0.086*
H4	1.1580	0.5870	0.9074	0.085*
H5	0.9829	0.6520	0.9471	0.076*
H6	0.8019	0.6688	0.7977	0.062*
H10a	0.4545	0.7320	0.5802	0.096*
H10b	0.3520	0.6842	0.5191	0.096*
H10c	0.4342	0.7257	0.4331	0.096*
H13	0.4197	0.6722	0.2143	0.055*
H14	0.2111	0.7151	0.1446	0.067*
H15	0.0076	0.6738	0.1987	0.077*
H16	0.0107	0.5892	0.3212	0.086*
H17	0.2179	0.5449	0.3897	0.069*
H19	0.2658	0.4749	−0.0464	0.061*
H20	0.3337	0.5420	0.1104	0.061*
H22	0.5700	0.4162	0.2900	0.053*
H25	0.2324	0.3822	−0.2107	0.065*
H26	0.2318	0.2915	−0.3165	0.076*
H27	0.3482	0.2107	−0.2272	0.078*
H28	0.4722	0.2190	−0.0333	0.073*
H30a	0.4751	0.3002	0.1862	0.066*
H30b	0.6045	0.3181	0.1129	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0580 (8)	0.0442 (7)	0.0571 (8)	0.0159 (6)	−0.0099 (6)	−0.0111 (6)
N1	0.0441 (8)	0.0394 (8)	0.0449 (8)	0.0056 (7)	−0.0037 (7)	−0.0057 (7)
N2	0.0490 (9)	0.0393 (8)	0.0499 (9)	0.0065 (7)	−0.0009 (7)	−0.0052 (7)
N3	0.0497 (9)	0.0390 (8)	0.0512 (9)	0.0068 (7)	−0.0103 (8)	−0.0062 (7)
C1	0.042 (1)	0.042 (1)	0.043 (1)	−0.004 (1)	−0.002 (1)	0.003 (1)
C2	0.050 (1)	0.060 (1)	0.064 (1)	0.008 (1)	−0.005 (1)	−0.013 (1)
C3	0.056 (1)	0.068 (1)	0.089 (2)	0.013 (1)	−0.014 (1)	−0.010 (1)
C4	0.066 (2)	0.068 (1)	0.074 (2)	0.004 (1)	−0.027 (1)	0.001 (1)
C5	0.066 (1)	0.073 (1)	0.048 (1)	−0.003 (1)	−0.009 (1)	−0.004 (1)
C6	0.051 (1)	0.056 (1)	0.049 (1)	−0.001 (1)	0.001 (1)	−0.003 (1)
C7	0.048 (1)	0.035 (1)	0.041 (1)	0.003 (1)	0.003 (1)	0.001 (1)
C8	0.044 (1)	0.035 (1)	0.038 (1)	0.005 (1)	0.001 (1)	0.000 (1)
C9	0.045 (1)	0.040 (1)	0.042 (1)	0.004 (1)	0.003 (1)	−0.001 (1)
C10	0.065 (1)	0.057 (1)	0.068 (1)	0.020 (1)	−0.005 (1)	−0.018 (1)
C11	0.045 (1)	0.036 (1)	0.039 (1)	0.001 (1)	0.001 (1)	0.004 (1)
C12	0.043 (1)	0.037 (1)	0.039 (1)	0.000 (1)	0.000 (1)	0.000 (1)
C13	0.045 (1)	0.045 (1)	0.049 (1)	0.000 (1)	0.005 (1)	0.007 (1)
C14	0.057 (1)	0.050 (1)	0.060 (1)	0.005 (1)	0.001 (1)	0.015 (1)
C15	0.043 (1)	0.074 (1)	0.074 (1)	0.009 (1)	−0.002 (1)	0.019 (1)
C16	0.041 (1)	0.090 (2)	0.085 (2)	−0.007 (1)	0.005 (1)	0.029 (1)
C17	0.051 (1)	0.056 (1)	0.064 (1)	−0.005 (1)	0.000 (1)	0.022 (1)
C18	0.040 (1)	0.046 (1)	0.044 (1)	−0.003 (1)	0.004 (1)	−0.002 (1)
C19	0.050 (1)	0.050 (1)	0.051 (1)	0.007 (1)	−0.010 (1)	−0.003 (1)
C20	0.059 (1)	0.040 (1)	0.052 (1)	0.010 (1)	−0.008 (1)	−0.004 (1)
C21	0.043 (1)	0.039 (1)	0.049 (1)	−0.001 (1)	−0.001 (1)	−0.003 (1)
C22	0.044 (1)	0.043 (1)	0.044 (1)	0.003 (1)	−0.003 (1)	0.001 (1)
C23	0.047 (1)	0.040 (1)	0.048 (1)	0.001 (1)	0.006 (1)	0.002 (1)
C24	0.041 (1)	0.048 (1)	0.047 (1)	−0.009 (1)	0.011 (1)	−0.008 (1)
C25	0.043 (1)	0.063 (1)	0.057 (1)	−0.007 (1)	0.005 (1)	−0.010 (1)
C26	0.051 (1)	0.081 (2)	0.059 (1)	−0.020 (1)	0.011 (1)	−0.024 (1)
C27	0.064 (1)	0.058 (1)	0.076 (2)	−0.018 (1)	0.023 (1)	−0.024 (1)
C28	0.067 (1)	0.047 (1)	0.070 (1)	−0.008 (1)	0.018 (1)	−0.010 (1)
C29	0.051 (1)	0.045 (1)	0.052 (1)	−0.004 (1)	0.014 (1)	−0.004 (1)
C30	0.066 (1)	0.043 (1)	0.057 (1)	0.006 (1)	0.003 (1)	−0.001 (1)

Geometric parameters (Å, º)

O1—C7	1.251 (2)	C23—C30	1.503 (2)
N1—C7	1.375 (2)	C24—C25	1.385 (2)
N1—N2	1.404 (2)	C24—C29	1.399 (2)
N1—C1	1.420 (2)	C25—C26	1.391 (3)
N2—C9	1.308 (2)	C26—C27	1.380 (3)
N3—C11	1.339 (2)	C27—C28	1.380 (3)
N3—C21	1.417 (2)	C28—C29	1.376 (2)
C1—C6	1.383 (2)	C29—C30	1.509 (2)
C1—C2	1.387 (2)	N3—H3n	0.97 (2)
C2—C3	1.381 (3)	C2—H2	0.93
C3—C4	1.369 (3)	C3—H3	0.93
C4—C5	1.374 (3)	C4—H4	0.93
C5—C6	1.378 (3)	C5—H5	0.93
C7—C8	1.441 (2)	C6—H6	0.93
C8—C11	1.397 (2)	C10—H10a	0.96
C8—C9	1.429 (2)	C10—H10b	0.96
C9—C10	1.496 (2)	C10—H10c	0.96
C11—C12	1.483 (2)	C13—H13	0.93
C12—C17	1.384 (2)	C14—H14	0.93
C12—C13	1.385 (2)	C15—H15	0.93
C13—C14	1.380 (2)	C16—H16	0.93
C14—C15	1.367 (3)	C17—H17	0.93
C15—C16	1.377 (3)	C19—H19	0.93
C16—C17	1.378 (3)	C20—H20	0.93
C18—C19	1.384 (2)	C22—H22	0.93
C18—C23	1.392 (2)	C25—H25	0.93
C18—C24	1.471 (2)	C26—H26	0.93
C19—C20	1.377 (2)	C27—H27	0.93
C20—C21	1.392 (2)	C28—H28	0.93
C21—C22	1.392 (2)	C30—H30a	0.97
C22—C23	1.382 (2)	C30—H30b	0.97
C7—N1—N2	111.6 (1)	C28—C29—C24	120.4 (2)
C7—N1—C1	128.1 (1)	C28—C29—C30	129.7 (2)
N2—N1—C1	118.8 (1)	C24—C29—C30	109.9 (2)
C9—N2—N1	106.4 (1)	C23—C30—C29	102.7 (1)
C11—N3—C21	133.0 (2)	C11—N3—H3n	111 (1)
C6—C1—C2	119.7 (2)	C21—N3—H3n	116 (1)
C6—C1—N1	119.6 (2)	C3—C2—H2	120.3
C2—C1—N1	120.7 (2)	C1—C2—H2	120.3
C3—C2—C1	119.4 (2)	C4—C3—H3	119.4
C4—C3—C2	121.1 (2)	C2—C3—H3	119.4
C3—C4—C5	119.1 (2)	C3—C4—H4	120.4
C4—C5—C6	120.9 (2)	C5—C4—H4	120.4
C5—C6—C1	119.7 (2)	C4—C5—H5	119.5
O1—C7—N1	125.9 (2)	C6—C5—H5	119.5
O1—C7—C8	129.0 (2)	C5—C6—H6	120.2
N1—C7—C8	105.0 (1)	C1—C6—H6	120.2
C11—C8—C9	132.5 (2)	C9—C10—H10a	109.5
C11—C8—C7	122.3 (2)	C9—C10—H10b	109.5
C9—C8—C7	105.2 (1)	H10a—C10—H10b	109.5
N2—C9—C8	111.8 (1)	C9—C10—H10c	109.5
N2—C9—C10	118.4 (2)	H10a—C10—H10c	109.5
C8—C9—C10	129.8 (2)	H10b—C10—H10c	109.5
N3—C11—C8	117.2 (2)	C14—C13—H13	119.9
N3—C11—C12	121.0 (1)	C12—C13—H13	119.9
C8—C11—C12	121.8 (2)	C15—C14—H14	120.0
C17—C12—C13	119.6 (2)	C13—C14—H14	120.0
C17—C12—C11	120.7 (2)	C14—C15—H15	119.9
C13—C12—C11	119.7 (2)	C16—C15—H15	119.9
C14—C13—C12	120.2 (2)	C15—C16—H16	119.8
C15—C14—C13	119.9 (2)	C17—C16—H16	119.8
C14—C15—C16	120.2 (2)	C16—C17—H17	120.2
C15—C16—C17	120.5 (2)	C12—C17—H17	120.2
C16—C17—C12	119.6 (2)	C20—C19—H19	120.1
C19—C18—C23	120.2 (2)	C18—C19—H19	120.1
C19—C18—C24	131.6 (2)	C19—C20—H20	119.8
C23—C18—C24	108.2 (2)	C21—C20—H20	119.8
C20—C19—C18	119.7 (2)	C23—C22—H22	120.2
C19—C20—C21	120.5 (2)	C21—C22—H22	120.2
C22—C21—C20	119.9 (2)	C24—C25—H25	120.7
C22—C21—N3	114.8 (2)	C26—C25—H25	120.7
C20—C21—N3	125.2 (2)	C27—C26—H26	119.6
C23—C22—C21	119.5 (2)	C25—C26—H26	119.6
C22—C23—C18	120.2 (2)	C26—C27—H27	119.6
C22—C23—C30	129.2 (2)	C28—C27—H27	119.6
C18—C23—C30	110.6 (2)	C29—C28—H28	120.4
C25—C24—C29	120.3 (2)	C27—C28—H28	120.4
C25—C24—C18	131.1 (2)	C23—C30—H30a	111.2
C29—C24—C18	108.6 (2)	C29—C30—H30a	111.2
C24—C25—C26	118.6 (2)	C23—C30—H30b	111.2
C27—C26—C25	120.7 (2)	C29—C30—H30b	111.2
C26—C27—C28	120.7 (2)	H30a—C30—H30b	109.1
C29—C28—C27	119.2 (2)
C7—N1—N2—C9	−1.1 (2)	C12—C13—C14—C15	0.5 (3)
C1—N1—N2—C9	−168.0 (2)	C13—C14—C15—C16	−0.3 (3)
C7—N1—C1—C6	−150.1 (2)	C14—C15—C16—C17	−0.2 (3)
N2—N1—C1—C6	14.5 (2)	C15—C16—C17—C12	0.4 (3)
C7—N1—C1—C2	29.0 (3)	C13—C12—C17—C16	−0.2 (3)
N2—N1—C1—C2	−166.5 (2)	C11—C12—C17—C16	178.4 (2)
C6—C1—C2—C3	1.7 (3)	C23—C18—C19—C20	0.8 (3)
N1—C1—C2—C3	−177.4 (2)	C24—C18—C19—C20	−179.3 (2)
C1—C2—C3—C4	−0.5 (3)	C18—C19—C20—C21	−0.4 (3)
C2—C3—C4—C5	−0.5 (3)	C19—C20—C21—C22	0.0 (3)
C3—C4—C5—C6	0.4 (3)	C19—C20—C21—N3	175.5 (2)
C4—C5—C6—C1	0.7 (3)	C11—N3—C21—C22	−164.2 (2)
C2—C1—C6—C5	−1.7 (3)	C11—N3—C21—C20	20.1 (3)
N1—C1—C6—C5	177.3 (2)	C20—C21—C22—C23	0.0 (3)
N2—N1—C7—O1	−179.1 (2)	N3—C21—C22—C23	−175.9 (2)
C1—N1—C7—O1	−13.7 (3)	C21—C22—C23—C18	0.3 (3)
N2—N1—C7—C8	0.9 (2)	C21—C22—C23—C30	−178.1 (2)
C1—N1—C7—C8	166.3 (2)	C19—C18—C23—C22	−0.7 (3)
O1—C7—C8—C11	1.0 (3)	C24—C18—C23—C22	179.3 (2)
N1—C7—C8—C11	−179.0 (2)	C19—C18—C23—C30	178.0 (2)
O1—C7—C8—C9	179.6 (2)	C24—C18—C23—C30	−2.0 (2)
N1—C7—C8—C9	−0.4 (2)	C19—C18—C24—C25	4.2 (3)
N1—N2—C9—C8	0.8 (2)	C23—C18—C24—C25	−175.8 (2)
N1—N2—C9—C10	180.0 (2)	C19—C18—C24—C29	−178.1 (2)
C11—C8—C9—N2	178.2 (2)	C23—C18—C24—C29	1.9 (2)
C7—C8—C9—N2	−0.3 (2)	C29—C24—C25—C26	0.5 (3)
C11—C8—C9—C10	−0.9 (3)	C18—C24—C25—C26	177.9 (2)
C7—C8—C9—C10	−179.4 (2)	C24—C25—C26—C27	0.7 (3)
C21—N3—C11—C8	−173.2 (2)	C25—C26—C27—C28	−0.9 (3)
C21—N3—C11—C12	8.1 (3)	C26—C27—C28—C29	0.0 (3)
C9—C8—C11—N3	−175.7 (2)	C27—C28—C29—C24	1.2 (3)
C7—C8—C11—N3	2.6 (3)	C27—C28—C29—C30	−176.8 (2)
C9—C8—C11—C12	3.0 (3)	C25—C24—C29—C28	−1.4 (3)
C7—C8—C11—C12	−178.8 (2)	C18—C24—C29—C28	−179.4 (2)
N3—C11—C12—C17	68.8 (2)	C25—C24—C29—C30	176.9 (2)
C8—C11—C12—C17	−109.9 (2)	C18—C24—C29—C30	−1.0 (2)
N3—C11—C12—C13	−112.7 (2)	C22—C23—C30—C29	179.9 (2)
C8—C11—C12—C13	68.6 (2)	C18—C23—C30—C29	1.4 (2)
C17—C12—C13—C14	−0.3 (3)	C28—C29—C30—C23	178.0 (2)
C11—C12—C13—C14	−178.8 (2)	C24—C29—C30—C23	−0.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3n···O1	0.97 (2)	1.80 (2)	2.671 (2)	147 (2)