3-Methyl-1-phenyl-4-[phen­yl(8-quinolylamino)methyl­ene]pyrazol-5(4H)-one

The title compound, C₂₆H₂₀N₄O, was synthesized by the reaction of 1-phenyl-3-methyl-4-benzoyl­pyrazol-5-one and 8-amino­quinoline. The mol­ecule exists in the enamine-keto tautomeric form.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.115
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.99 Deg.
PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size .......       0.95 mm

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C23    -   C24     ..       5.01 su
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C10

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   3 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

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

3-Methyl-1-phenyl-4-[phenyl(8-quinolylamino)methylene]pyrazol-5(4H)-one

Crystal data

C26H20N4O	F(000) = 848
Mr = 404.46	Dx = 1.295 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5842 reflections
a = 7.387 (1) Å	θ = 2.5–28.2°
b = 26.563 (4) Å	µ = 0.08 mm^−1
c = 10.7360 (15) Å	T = 273 K
β = 99.937 (2)°	Block, yellow
V = 2075.0 (5) Å^3	0.95 × 0.28 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3657 independent reflections
Radiation source: fine-focus sealed tube	3227 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
φ and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.927, Tmax = 0.992	k = −31→31
10524 measured reflections	l = −12→8

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)] = 0.037	Hydrogen site location: difference Fourier map
wR(F^2) = 0.115	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.077P)^2 + 0.2722P] where P = (Fo^2 + 2Fc^2)/3
3657 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

Experimental. IR (KBr, ν cm^-1): 1637, 1587, 1571, 1498, 1456, 1379, 1317, 1263, 1176, 1147, 1007, 793, 775, 741,696, 656, 588.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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.

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

	x	y	z	Uiso*/Ueq
O1	0.02577 (13)	0.14001 (4)	0.05656 (8)	0.0511 (3)
N1	0.28269 (15)	0.18678 (4)	0.14581 (10)	0.0439 (3)
N2	0.38107 (15)	0.19717 (4)	0.26687 (10)	0.0463 (3)
N3	−0.12845 (15)	0.09768 (4)	0.24324 (11)	0.0465 (3)
H3	−0.1119	0.1000	0.1661	0.056*
N4	−0.18477 (16)	0.01280 (4)	0.10664 (11)	0.0500 (3)
C1	0.12944 (17)	0.15762 (5)	0.14976 (12)	0.0403 (3)
C2	0.12395 (17)	0.15226 (4)	0.28303 (11)	0.0394 (3)
C3	0.28658 (18)	0.17755 (5)	0.34699 (12)	0.0422 (3)
C4	0.36315 (18)	0.19684 (4)	0.03796 (12)	0.0406 (3)
C5	0.25271 (19)	0.21138 (5)	−0.07387 (12)	0.0457 (3)
H5	0.1269	0.2156	−0.0774	0.055*
C6	0.3308 (2)	0.21961 (6)	−0.18006 (13)	0.0554 (4)
H6	0.2570	0.2292	−0.2555	0.067*
C7	0.5168 (2)	0.21382 (6)	−0.17526 (14)	0.0602 (4)
H7	0.5686	0.2197	−0.2469	0.072*
C8	0.6263 (2)	0.19926 (6)	−0.06383 (15)	0.0578 (4)
H8	0.7519	0.1950	−0.0609	0.069*
C9	0.55082 (19)	0.19099 (5)	0.04330 (13)	0.0483 (3)
H9	0.6253	0.1816	0.1186	0.058*
C10	0.3601 (2)	0.18213 (6)	0.48465 (13)	0.0548 (4)
H10A	0.4712	0.2016	0.4966	0.082*
H10B	0.3856	0.1492	0.5202	0.082*
H10C	0.2708	0.1985	0.5259	0.082*
C11	−0.00985 (17)	0.12400 (4)	0.32710 (12)	0.0392 (3)
C12	−0.02264 (17)	0.12140 (5)	0.46328 (12)	0.0403 (3)
C13	−0.06639 (19)	0.16417 (5)	0.52596 (13)	0.0492 (3)
H13	−0.0865	0.1945	0.4826	0.059*
C14	−0.0802 (2)	0.16186 (7)	0.65234 (14)	0.0593 (4)
H14	−0.1106	0.1906	0.6938	0.071*
C15	−0.0490 (2)	0.11720 (7)	0.71726 (15)	0.0656 (4)
H15	−0.0582	0.1157	0.8025	0.079*
C16	−0.0043 (2)	0.07485 (7)	0.65572 (15)	0.0632 (4)
H16	0.0177	0.0448	0.7000	0.076*
C17	0.00851 (19)	0.07637 (5)	0.52927 (13)	0.0504 (3)
H17	0.0378	0.0474	0.4883	0.060*
C18	−0.27690 (18)	0.06668 (5)	0.26272 (13)	0.0450 (3)
C19	−0.3946 (2)	0.07838 (6)	0.34361 (15)	0.0591 (4)
H19	−0.3802	0.1084	0.3888	0.071*
C20	−0.5369 (2)	0.04524 (8)	0.35857 (19)	0.0734 (5)
H20	−0.6158	0.0534	0.4143	0.088*
C21	−0.5610 (2)	0.00136 (7)	0.29262 (19)	0.0747 (5)
H21	−0.6545	−0.0205	0.3051	0.090*
C22	−0.4457 (2)	−0.01127 (6)	0.20545 (16)	0.0579 (4)
C23	−0.4639 (2)	−0.05549 (6)	0.1300 (2)	0.0743 (5)
H23	−0.5562	−0.0786	0.1368	0.089*
C24	−0.3474 (3)	−0.06386 (6)	0.0487 (2)	0.0745 (5)
H24	−0.3586	−0.0927	−0.0012	0.089*
C25	−0.2098 (2)	−0.02883 (6)	0.04012 (16)	0.0623 (4)
H25	−0.1305	−0.0354	−0.0164	0.075*
C26	−0.30175 (18)	0.02179 (5)	0.18954 (13)	0.0454 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0522 (6)	0.0616 (6)	0.0394 (5)	−0.0163 (4)	0.0081 (4)	−0.0047 (4)
N1	0.0470 (6)	0.0498 (6)	0.0357 (6)	−0.0122 (5)	0.0093 (5)	−0.0016 (4)
N2	0.0487 (6)	0.0516 (6)	0.0383 (6)	−0.0099 (5)	0.0072 (5)	−0.0039 (5)
N3	0.0514 (6)	0.0479 (6)	0.0432 (6)	−0.0111 (5)	0.0160 (5)	−0.0043 (5)
N4	0.0489 (7)	0.0491 (7)	0.0516 (7)	−0.0015 (5)	0.0071 (5)	−0.0054 (5)
C1	0.0429 (7)	0.0382 (6)	0.0406 (7)	−0.0034 (5)	0.0095 (5)	−0.0020 (5)
C2	0.0445 (7)	0.0369 (6)	0.0381 (7)	−0.0004 (5)	0.0106 (5)	−0.0011 (5)
C3	0.0478 (7)	0.0401 (6)	0.0395 (7)	−0.0014 (5)	0.0097 (5)	−0.0025 (5)
C4	0.0471 (7)	0.0344 (6)	0.0421 (7)	−0.0083 (5)	0.0127 (5)	−0.0033 (5)
C5	0.0450 (7)	0.0490 (7)	0.0432 (7)	−0.0061 (6)	0.0081 (5)	−0.0008 (6)
C6	0.0614 (9)	0.0641 (9)	0.0408 (7)	−0.0120 (7)	0.0089 (6)	0.0006 (6)
C7	0.0648 (10)	0.0723 (10)	0.0483 (8)	−0.0161 (8)	0.0231 (7)	−0.0062 (7)
C8	0.0473 (8)	0.0664 (9)	0.0637 (9)	−0.0076 (7)	0.0207 (7)	−0.0063 (7)
C9	0.0467 (8)	0.0489 (7)	0.0492 (8)	−0.0032 (6)	0.0078 (6)	0.0007 (6)
C10	0.0566 (8)	0.0660 (9)	0.0414 (8)	−0.0078 (7)	0.0079 (6)	−0.0058 (6)
C11	0.0431 (7)	0.0331 (6)	0.0429 (7)	0.0035 (5)	0.0117 (5)	−0.0002 (5)
C12	0.0404 (6)	0.0400 (6)	0.0423 (7)	−0.0005 (5)	0.0120 (5)	0.0023 (5)
C13	0.0562 (8)	0.0456 (7)	0.0490 (8)	0.0031 (6)	0.0178 (6)	−0.0005 (6)
C14	0.0594 (9)	0.0727 (10)	0.0495 (8)	−0.0008 (7)	0.0195 (7)	−0.0116 (7)
C15	0.0612 (9)	0.0965 (13)	0.0410 (8)	−0.0060 (9)	0.0145 (7)	0.0045 (8)
C16	0.0613 (9)	0.0716 (10)	0.0561 (9)	0.0010 (8)	0.0085 (7)	0.0256 (8)
C17	0.0515 (8)	0.0450 (7)	0.0561 (8)	0.0034 (6)	0.0131 (6)	0.0077 (6)
C18	0.0413 (7)	0.0443 (7)	0.0503 (7)	−0.0034 (5)	0.0102 (6)	0.0034 (6)
C19	0.0522 (8)	0.0613 (9)	0.0675 (10)	−0.0013 (7)	0.0207 (7)	−0.0037 (7)
C20	0.0544 (9)	0.0866 (12)	0.0864 (12)	−0.0077 (8)	0.0328 (9)	−0.0001 (10)
C21	0.0547 (10)	0.0743 (11)	0.0991 (13)	−0.0199 (8)	0.0241 (9)	0.0073 (10)
C22	0.0476 (8)	0.0504 (8)	0.0738 (10)	−0.0085 (6)	0.0051 (7)	0.0070 (7)
C23	0.0621 (10)	0.0503 (9)	0.1058 (14)	−0.0173 (8)	0.0015 (10)	0.0014 (9)
C24	0.0705 (11)	0.0514 (9)	0.0969 (13)	−0.0051 (8)	0.0011 (10)	−0.0184 (9)
C25	0.0617 (9)	0.0556 (9)	0.0675 (10)	0.0011 (7)	0.0049 (8)	−0.0128 (7)
C26	0.0405 (7)	0.0432 (7)	0.0506 (8)	−0.0012 (5)	0.0033 (6)	0.0056 (5)

Geometric parameters (Å, º)

O1—C1	1.2418 (15)	C11—C12	1.4829 (18)
N1—C1	1.3783 (16)	C12—C13	1.3869 (18)
N1—N2	1.4027 (15)	C12—C17	1.3891 (19)
N1—C4	1.4153 (16)	C13—C14	1.379 (2)
N2—C3	1.3060 (16)	C13—H13	0.9300
N3—C11	1.3396 (16)	C14—C15	1.375 (2)
N3—C18	1.4154 (16)	C14—H14	0.9300
N3—H3	0.8600	C15—C16	1.374 (2)
N4—C25	1.3120 (19)	C15—H15	0.9300
N4—C26	1.3643 (18)	C16—C17	1.377 (2)
C1—C2	1.4454 (17)	C16—H16	0.9300
C2—C11	1.3877 (17)	C17—H17	0.9300
C2—C3	1.4428 (18)	C18—C19	1.366 (2)
C3—C10	1.4890 (18)	C18—C26	1.4224 (19)
C4—C5	1.3849 (19)	C19—C20	1.401 (2)
C4—C9	1.3863 (19)	C19—H19	0.9300
C5—C6	1.3811 (19)	C20—C21	1.359 (3)
C5—H5	0.9300	C20—H20	0.9300
C6—C7	1.374 (2)	C21—C22	1.410 (2)
C6—H6	0.9300	C21—H21	0.9300
C7—C8	1.379 (2)	C22—C26	1.4122 (19)
C7—H7	0.9300	C22—C23	1.420 (2)
C8—C9	1.379 (2)	C23—C24	1.346 (3)
C8—H8	0.9300	C23—H23	0.9300
C9—H9	0.9300	C24—C25	1.393 (3)
C10—H10A	0.9600	C24—H24	0.9300
C10—H10B	0.9600	C25—H25	0.9300
C10—H10C	0.9600
C1—N1—N2	112.27 (10)	C13—C12—C11	120.01 (11)
C1—N1—C4	126.47 (10)	C17—C12—C11	120.66 (11)
N2—N1—C4	119.82 (10)	C14—C13—C12	120.25 (13)
C3—N2—N1	106.35 (10)	C14—C13—H13	119.9
C11—N3—C18	129.62 (11)	C12—C13—H13	119.9
C11—N3—H3	115.2	C15—C14—C13	120.18 (14)
C18—N3—H3	115.2	C15—C14—H14	119.9
C25—N4—C26	117.20 (13)	C13—C14—H14	119.9
O1—C1—N1	125.63 (11)	C16—C15—C14	119.73 (14)
O1—C1—C2	129.92 (11)	C16—C15—H15	120.1
N1—C1—C2	104.44 (10)	C14—C15—H15	120.1
C11—C2—C3	132.31 (11)	C15—C16—C17	120.88 (14)
C11—C2—C1	122.29 (11)	C15—C16—H16	119.6
C3—C2—C1	105.19 (10)	C17—C16—H16	119.6
N2—C3—C2	111.59 (11)	C16—C17—C12	119.63 (13)
N2—C3—C10	118.45 (12)	C16—C17—H17	120.2
C2—C3—C10	129.91 (12)	C12—C17—H17	120.2
C5—C4—C9	120.16 (12)	C19—C18—N3	123.77 (13)
C5—C4—N1	119.62 (12)	C19—C18—C26	120.40 (12)
C9—C4—N1	120.20 (12)	N3—C18—C26	115.82 (11)
C6—C5—C4	119.49 (13)	C18—C19—C20	120.14 (16)
C6—C5—H5	120.3	C18—C19—H19	119.9
C4—C5—H5	120.3	C20—C19—H19	119.9
C7—C6—C5	120.57 (14)	C21—C20—C19	120.83 (16)
C7—C6—H6	119.7	C21—C20—H20	119.6
C5—C6—H6	119.7	C19—C20—H20	119.6
C6—C7—C8	119.78 (13)	C20—C21—C22	120.65 (14)
C6—C7—H7	120.1	C20—C21—H21	119.7
C8—C7—H7	120.1	C22—C21—H21	119.7
C7—C8—C9	120.49 (14)	C21—C22—C26	119.07 (14)
C7—C8—H8	119.8	C21—C22—C23	124.53 (15)
C9—C8—H8	119.8	C26—C22—C23	116.39 (15)
C8—C9—C4	119.51 (13)	C24—C23—C22	119.90 (15)
C8—C9—H9	120.2	C24—C23—H23	120.0
C4—C9—H9	120.2	C22—C23—H23	120.0
C3—C10—H10A	109.5	C23—C24—C25	119.21 (16)
C3—C10—H10B	109.5	C23—C24—H24	120.4
H10A—C10—H10B	109.5	C25—C24—H24	120.4
C3—C10—H10C	109.5	N4—C25—C24	124.26 (16)
H10A—C10—H10C	109.5	N4—C25—H25	117.9
H10B—C10—H10C	109.5	C24—C25—H25	117.9
N3—C11—C2	118.35 (11)	N4—C26—C22	123.03 (13)
N3—C11—C12	119.53 (11)	N4—C26—C18	118.11 (11)
C2—C11—C12	122.12 (11)	C22—C26—C18	118.86 (13)
C13—C12—C17	119.34 (12)