4-[(Z)-(2,4-Dimethyl­phenyl­amino)phenyl­methyl­ene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

The NH unit on the exocyclic C=C double bond in the title compound, C₂₅H₂₃N₃O, inter­acts with the carbonyl group through an intra­molecular hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.054
• wR factor = 0.130
• Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         44 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C7     -   C8      ..       5.74 su
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C25 H23 N3 O

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

4-[(Z)-(2,4-Dimethylphenylamino)phenylmethylene]-3-methyl-1-phenyl-1H- pyrazol-5(4H)-one

Crystal data

C25H23N3O	Z = 2
Mr = 381.46	F(000) = 404
Triclinic, P1	Dx = 1.223 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.909 (1) Å	Cell parameters from 1384 reflections
b = 11.200 (1) Å	θ = 2.7–20.4°
c = 13.239 (1) Å	µ = 0.08 mm^−1
α = 106.410 (2)°	T = 295 K
β = 106.327 (2)°	Block, yellow
γ = 100.390 (2)°	0.10 × 0.06 × 0.04 mm
V = 1035.6 (2) Å^3

Data collection

Bruker SMART area-detector diffractometer	2018 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.078
Graphite monochromator	θmax = 27.5°, θmin = 1.7°
ω and φ scans	h = −10→10
10060 measured reflections	k = −14→14
4633 independent reflections	l = −17→17

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.130	H-atom parameters constrained
S = 0.83	w = 1/[σ^2(Fo^2) + (0.047P)^2] where P = (Fo^2 + 2Fc^2)/3
4633 reflections	(Δ/σ)max = 0.001
265 parameters	Δρmax = 0.18 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	1.2316 (2)	0.14575 (15)	0.75272 (13)	0.0714 (5)
N1	1.5387 (2)	0.26624 (17)	0.85053 (14)	0.0569 (5)
N2	1.6439 (2)	0.39594 (18)	0.88910 (14)	0.0613 (5)
N3	1.0293 (2)	0.30363 (19)	0.69866 (14)	0.0610 (5)
H3N	1.0457	0.2308	0.7020	0.073
C1	1.6299 (3)	0.1689 (2)	0.85790 (17)	0.0579 (6)
C2	1.5392 (3)	0.0537 (2)	0.8613 (2)	0.0835 (8)
H2	1.4181	0.0391	0.8583	0.100*
C3	1.6288 (4)	−0.0393 (2)	0.8690 (2)	0.0960 (9)
H3	1.5672	−0.1169	0.8714	0.115*
C4	1.8064 (4)	−0.0201 (3)	0.8733 (2)	0.0916 (9)
H4	1.8652	−0.0842	0.8777	0.110*
C5	1.8966 (4)	0.0942 (3)	0.8709 (2)	0.0907 (9)
H5	2.0178	0.1081	0.8742	0.109*
C6	1.8094 (3)	0.1898 (3)	0.8637 (2)	0.0735 (7)
H6	1.8722	0.2679	0.8627	0.088*
C7	1.3562 (3)	0.2510 (2)	0.79753 (18)	0.0560 (6)
C8	1.3434 (3)	0.3791 (2)	0.80392 (16)	0.0514 (5)
C9	1.5279 (3)	0.4613 (2)	0.86177 (17)	0.0560 (6)
C10	1.6025 (3)	0.6043 (2)	0.8930 (2)	0.0764 (7)
H10A	1.7338	0.6288	0.9276	0.115*
H10B	1.5515	0.6492	0.9449	0.115*
H10C	1.5703	0.6266	0.8266	0.115*
C11	1.1805 (3)	0.4038 (2)	0.75300 (17)	0.0527 (6)
C12	1.1714 (3)	0.5336 (2)	0.75121 (18)	0.0512 (5)
C13	1.1637 (3)	0.5623 (2)	0.65563 (19)	0.0676 (7)
H13	1.1664	0.5003	0.5928	0.081*
C14	1.1518 (3)	0.6829 (3)	0.6531 (2)	0.0807 (8)
H14	1.1476	0.7021	0.5886	0.097*
C15	1.1463 (3)	0.7743 (3)	0.7449 (3)	0.0803 (8)
H15	1.1366	0.8550	0.7424	0.096*
C16	1.1551 (3)	0.7474 (2)	0.8403 (2)	0.0776 (7)
H16	1.1518	0.8099	0.9028	0.093*
C17	1.1687 (3)	0.6281 (2)	0.84409 (19)	0.0652 (6)
H17	1.1761	0.6106	0.9096	0.078*
C18	0.8445 (3)	0.2952 (2)	0.63569 (18)	0.0539 (6)
C19	0.7652 (3)	0.3951 (2)	0.66224 (19)	0.0686 (7)
H19	0.8316	0.4706	0.7238	0.082*
C20	0.5878 (3)	0.3827 (2)	0.5975 (2)	0.0700 (7)
H20	0.5364	0.4506	0.6158	0.084*
C21	0.4858 (3)	0.2715 (3)	0.5065 (2)	0.0643 (6)
C22	0.5661 (3)	0.1726 (2)	0.48343 (19)	0.0666 (6)
H22	0.4977	0.0963	0.4232	0.080*
C23	0.7434 (3)	0.1813 (2)	0.54563 (19)	0.0568 (6)
C24	0.2931 (3)	0.2602 (3)	0.4367 (2)	0.1006 (9)
H24A	0.2945	0.3295	0.4075	0.151*
H24B	0.2180	0.2654	0.4827	0.151*
H24C	0.2439	0.1784	0.3755	0.151*
C25	0.8245 (3)	0.0713 (2)	0.5134 (2)	0.0881 (8)
H25A	0.7379	0.0041	0.4461	0.132*
H25B	0.8526	0.0374	0.5732	0.132*
H25C	0.9350	0.1021	0.5004	0.132*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0513 (9)	0.0629 (11)	0.0876 (12)	0.0201 (9)	0.0088 (9)	0.0217 (9)
N1	0.0480 (11)	0.0505 (12)	0.0667 (12)	0.0202 (9)	0.0083 (9)	0.0206 (10)
N2	0.0531 (11)	0.0623 (13)	0.0635 (12)	0.0181 (10)	0.0104 (9)	0.0239 (10)
N3	0.0561 (12)	0.0543 (13)	0.0713 (13)	0.0258 (10)	0.0125 (10)	0.0240 (10)
C1	0.0535 (14)	0.0608 (16)	0.0562 (14)	0.0274 (12)	0.0091 (11)	0.0188 (12)
C2	0.0534 (15)	0.0687 (18)	0.115 (2)	0.0248 (14)	0.0083 (14)	0.0297 (16)
C3	0.0731 (19)	0.0611 (18)	0.131 (3)	0.0272 (15)	0.0004 (17)	0.0318 (17)
C4	0.086 (2)	0.087 (2)	0.096 (2)	0.0542 (18)	0.0119 (17)	0.0250 (18)
C5	0.0718 (18)	0.129 (3)	0.099 (2)	0.059 (2)	0.0362 (16)	0.056 (2)
C6	0.0661 (17)	0.0918 (19)	0.0852 (18)	0.0401 (15)	0.0324 (14)	0.0475 (15)
C7	0.0468 (14)	0.0612 (16)	0.0564 (14)	0.0225 (12)	0.0102 (11)	0.0191 (12)
C8	0.0511 (13)	0.0499 (14)	0.0517 (13)	0.0227 (11)	0.0125 (11)	0.0162 (11)
C9	0.0560 (14)	0.0596 (15)	0.0499 (13)	0.0213 (12)	0.0118 (11)	0.0195 (12)
C10	0.0697 (16)	0.0620 (17)	0.0854 (18)	0.0181 (13)	0.0119 (14)	0.0238 (14)
C11	0.0538 (14)	0.0602 (15)	0.0430 (12)	0.0207 (12)	0.0146 (11)	0.0162 (11)
C12	0.0464 (12)	0.0570 (15)	0.0494 (13)	0.0213 (11)	0.0092 (10)	0.0209 (12)
C13	0.0636 (15)	0.0862 (19)	0.0605 (15)	0.0274 (14)	0.0210 (12)	0.0334 (14)
C14	0.0695 (17)	0.098 (2)	0.084 (2)	0.0190 (16)	0.0178 (15)	0.0577 (19)
C15	0.0643 (16)	0.0588 (17)	0.098 (2)	0.0155 (14)	−0.0071 (16)	0.0352 (17)
C16	0.0729 (16)	0.0641 (18)	0.0725 (18)	0.0295 (14)	−0.0025 (13)	0.0118 (14)
C17	0.0756 (16)	0.0630 (16)	0.0530 (14)	0.0326 (13)	0.0099 (12)	0.0194 (13)
C18	0.0488 (13)	0.0611 (15)	0.0570 (14)	0.0242 (12)	0.0169 (11)	0.0250 (13)
C19	0.0573 (15)	0.0679 (17)	0.0704 (16)	0.0283 (13)	0.0155 (13)	0.0097 (13)
C20	0.0580 (15)	0.0692 (17)	0.0813 (18)	0.0328 (14)	0.0190 (14)	0.0206 (15)
C21	0.0491 (14)	0.0742 (17)	0.0753 (17)	0.0243 (13)	0.0185 (13)	0.0335 (15)
C22	0.0520 (14)	0.0677 (17)	0.0703 (16)	0.0160 (13)	0.0134 (12)	0.0187 (13)
C23	0.0508 (14)	0.0576 (15)	0.0654 (15)	0.0201 (12)	0.0221 (12)	0.0221 (13)
C24	0.0584 (16)	0.108 (2)	0.117 (2)	0.0304 (16)	0.0028 (16)	0.0362 (19)
C25	0.0687 (17)	0.0681 (17)	0.114 (2)	0.0277 (14)	0.0237 (16)	0.0148 (15)

Geometric parameters (Å, º)

O1—C7	1.253 (2)	C12—C17	1.386 (3)
N1—C7	1.371 (2)	C13—C14	1.380 (3)
N1—N2	1.403 (2)	C13—H13	0.9300
N1—C1	1.422 (2)	C14—C15	1.368 (3)
N2—C9	1.309 (2)	C14—H14	0.9300
N3—C11	1.335 (2)	C15—C16	1.366 (3)
N3—C18	1.436 (2)	C15—H15	0.9300
N3—H3N	0.8600	C16—C17	1.373 (3)
C1—C6	1.373 (3)	C16—H16	0.9300
C1—C2	1.378 (3)	C17—H17	0.9300
C2—C3	1.372 (3)	C18—C19	1.386 (3)
C2—H2	0.9300	C18—C23	1.388 (3)
C3—C4	1.365 (3)	C19—C20	1.381 (3)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.361 (3)	C20—C21	1.377 (3)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.385 (3)	C21—C22	1.377 (3)
C5—H5	0.9300	C21—C24	1.505 (3)
C6—H6	0.9300	C22—C23	1.382 (3)
C7—C8	1.436 (3)	C22—H22	0.9300
C8—C11	1.392 (3)	C23—C25	1.501 (3)
C8—C9	1.433 (3)	C24—H24A	0.9600
C9—C10	1.494 (3)	C24—H24B	0.9600
C10—H10A	0.9600	C24—H24C	0.9600
C10—H10B	0.9600	C25—H25A	0.9600
C10—H10C	0.9600	C25—H25B	0.9600
C11—C12	1.475 (3)	C25—H25C	0.9600
C12—C13	1.379 (3)
C7—N1—N2	111.97 (17)	C14—C13—C12	120.2 (2)
C7—N1—C1	128.56 (19)	C14—C13—H13	119.9
N2—N1—C1	119.00 (17)	C12—C13—H13	119.9
C9—N2—N1	105.94 (16)	C15—C14—C13	120.3 (2)
C11—N3—C18	131.78 (19)	C15—C14—H14	119.9
C11—N3—H3N	114.1	C13—C14—H14	119.9
C18—N3—H3N	114.1	C16—C15—C14	120.2 (2)
C6—C1—C2	119.6 (2)	C16—C15—H15	119.9
C6—C1—N1	120.4 (2)	C14—C15—H15	119.9
C2—C1—N1	120.0 (2)	C15—C16—C17	120.0 (2)
C3—C2—C1	119.6 (2)	C15—C16—H16	120.0
C3—C2—H2	120.2	C17—C16—H16	120.0
C1—C2—H2	120.2	C16—C17—C12	120.6 (2)
C4—C3—C2	121.2 (3)	C16—C17—H17	119.7
C4—C3—H3	119.4	C12—C17—H17	119.7
C2—C3—H3	119.4	C19—C18—C23	119.8 (2)
C5—C4—C3	119.2 (3)	C19—C18—N3	122.6 (2)
C5—C4—H4	120.4	C23—C18—N3	117.6 (2)
C3—C4—H4	120.4	C20—C19—C18	120.2 (2)
C4—C5—C6	120.6 (3)	C20—C19—H19	119.9
C4—C5—H5	119.7	C18—C19—H19	119.9
C6—C5—H5	119.7	C21—C20—C19	121.1 (2)
C1—C6—C5	119.8 (2)	C21—C20—H20	119.4
C1—C6—H6	120.1	C19—C20—H20	119.4
C5—C6—H6	120.1	C22—C21—C20	117.6 (2)
O1—C7—N1	125.8 (2)	C22—C21—C24	122.1 (2)
O1—C7—C8	129.00 (19)	C20—C21—C24	120.3 (2)
N1—C7—C8	105.17 (19)	C21—C22—C23	123.1 (2)
C11—C8—C9	131.9 (2)	C21—C22—H22	118.5
C11—C8—C7	122.9 (2)	C23—C22—H22	118.5
C9—C8—C7	104.98 (18)	C22—C23—C18	118.2 (2)
N2—C9—C8	111.93 (19)	C22—C23—C25	120.3 (2)
N2—C9—C10	117.8 (2)	C18—C23—C25	121.5 (2)
C8—C9—C10	130.2 (2)	C21—C24—H24A	109.5
C9—C10—H10A	109.5	C21—C24—H24B	109.5
C9—C10—H10B	109.5	H24A—C24—H24B	109.5
H10A—C10—H10B	109.5	C21—C24—H24C	109.5
C9—C10—H10C	109.5	H24A—C24—H24C	109.5
H10A—C10—H10C	109.5	H24B—C24—H24C	109.5
H10B—C10—H10C	109.5	C23—C25—H25A	109.5
N3—C11—C8	117.88 (19)	C23—C25—H25B	109.5
N3—C11—C12	119.33 (18)	H25A—C25—H25B	109.5
C8—C11—C12	122.69 (19)	C23—C25—H25C	109.5
C13—C12—C17	118.8 (2)	H25A—C25—H25C	109.5
C13—C12—C11	120.1 (2)	H25B—C25—H25C	109.5
C17—C12—C11	121.16 (19)
C7—N1—N2—C9	0.8 (2)	C7—C8—C11—N3	1.9 (3)
C1—N1—N2—C9	173.61 (18)	C9—C8—C11—C12	−0.5 (4)
C7—N1—C1—C6	148.6 (2)	C7—C8—C11—C12	−174.40 (19)
N2—N1—C1—C6	−22.9 (3)	N3—C11—C12—C13	−75.1 (3)
C7—N1—C1—C2	−32.5 (3)	C8—C11—C12—C13	101.1 (2)
N2—N1—C1—C2	156.0 (2)	N3—C11—C12—C17	104.3 (2)
C6—C1—C2—C3	−0.8 (4)	C8—C11—C12—C17	−79.5 (3)
N1—C1—C2—C3	−179.6 (2)	C17—C12—C13—C14	−0.5 (3)
C1—C2—C3—C4	−0.1 (4)	C11—C12—C13—C14	178.81 (19)
C2—C3—C4—C5	0.7 (4)	C12—C13—C14—C15	−0.5 (3)
C3—C4—C5—C6	−0.3 (4)	C13—C14—C15—C16	0.9 (4)
C2—C1—C6—C5	1.1 (4)	C14—C15—C16—C17	−0.3 (4)
N1—C1—C6—C5	180.0 (2)	C15—C16—C17—C12	−0.8 (3)
C4—C5—C6—C1	−0.5 (4)	C13—C12—C17—C16	1.2 (3)
N2—N1—C7—O1	178.31 (19)	C11—C12—C17—C16	−178.17 (19)
C1—N1—C7—O1	6.4 (4)	C11—N3—C18—C19	−32.7 (3)
N2—N1—C7—C8	−0.8 (2)	C11—N3—C18—C23	147.9 (2)
C1—N1—C7—C8	−172.76 (19)	C23—C18—C19—C20	−1.7 (3)
O1—C7—C8—C11	−3.3 (4)	N3—C18—C19—C20	178.85 (19)
N1—C7—C8—C11	175.84 (19)	C18—C19—C20—C21	0.6 (3)
O1—C7—C8—C9	−178.6 (2)	C19—C20—C21—C22	0.9 (3)
N1—C7—C8—C9	0.5 (2)	C19—C20—C21—C24	−179.7 (2)
N1—N2—C9—C8	−0.4 (2)	C20—C21—C22—C23	−1.3 (3)
N1—N2—C9—C10	179.92 (18)	C24—C21—C22—C23	179.3 (2)
C11—C8—C9—N2	−174.8 (2)	C21—C22—C23—C18	0.2 (3)
C7—C8—C9—N2	0.0 (2)	C21—C22—C23—C25	−178.0 (2)
C11—C8—C9—C10	4.8 (4)	C19—C18—C23—C22	1.3 (3)
C7—C8—C9—C10	179.5 (2)	N3—C18—C23—C22	−179.21 (18)
C18—N3—C11—C8	−177.90 (19)	C19—C18—C23—C25	179.5 (2)
C18—N3—C11—C12	−1.5 (3)	N3—C18—C23—C25	−1.1 (3)
C9—C8—C11—N3	175.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1	0.86	1.96	2.700 (2)	144