1,5-Dimethyl-2-phenyl-4-[(1H-pyrrol-2-ylmethyl­ene)amino]pyrazol-3(2H)-one

In the crystal structure of the title compound, C₁₆H₁₆N₄O, the mol­ecules are linked via weak inter­molecular N—H...O hydrogen bonds, forming an extended supra­molecular arrangement.

Key indicators

• Single-crystal X-ray study
• T = 113 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.121
• Data-to-parameter ratio = 17.0

checkCIF/PLATON results

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Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         700 Deg.

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

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

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Computing details

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2005); software used to prepare material for publication: CrystalStructure.

1,5-Dimethyl-2-phenyl-4-[(1H-pyrrol-2-ylmethylene)amino]pyrazol-3(2H)-one

Crystal data

C16H16N4O	Z = 2
Mr = 280.33	F(000) = 296
Triclinic, P1	Dx = 1.313 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71070 Å
a = 7.3142 (4) Å	Cell parameters from 1913 reflections
b = 7.3170 (3) Å	θ = 2.8–27.9°
c = 13.5485 (6) Å	µ = 0.09 mm^−1
α = 80.791 (7)°	T = 113 K
β = 82.639 (7)°	Prism, colourless
γ = 86.330 (7)°	0.20 × 0.16 × 0.14 mm
V = 709.14 (6) Å^3

Data collection

Rigaku Saturn diffractometer	3346 independent reflections
Radiation source: rotating anode	2367 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.034
Detector resolution: 7.31 pixels mm^-1	θmax = 27.9°, θmin = 2.8°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→9
Tmin = 0.983, Tmax = 0.988	l = −17→17
8890 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.0627P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
3346 reflections	Δρmax = 0.23 e Å^−3
197 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.038 (7)

Special details

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	0.34727 (13)	0.22414 (15)	0.40364 (7)	0.0264 (3)
N1	0.07153 (15)	0.32447 (17)	0.34154 (9)	0.0221 (3)
N2	−0.11405 (15)	0.33548 (17)	0.37902 (9)	0.0214 (3)
N3	0.07838 (15)	0.17397 (16)	0.60771 (9)	0.0203 (3)
N4	0.43612 (17)	−0.06065 (17)	0.74861 (10)	0.0235 (3)
H4	0.514 (2)	−0.108 (2)	0.7051 (13)	0.035*
C1	0.17495 (19)	0.25423 (19)	0.41823 (11)	0.0206 (3)
C2	0.04575 (18)	0.22915 (19)	0.50753 (10)	0.0190 (3)
C3	−0.12617 (19)	0.28459 (19)	0.47976 (10)	0.0195 (3)
C4	0.13535 (19)	0.3825 (2)	0.23791 (11)	0.0208 (3)
C5	0.2531 (2)	0.5278 (2)	0.21260 (12)	0.0288 (4)
H5	0.2910	0.5869	0.2636	0.035*
C6	0.3152 (2)	0.5864 (2)	0.11228 (13)	0.0364 (4)
H6	0.3979	0.6846	0.0945	0.044*
C7	0.2575 (2)	0.5026 (3)	0.03801 (12)	0.0365 (4)
H7	0.2980	0.5451	−0.0308	0.044*
C8	0.1406 (2)	0.3570 (2)	0.06382 (12)	0.0330 (4)
H8	0.1017	0.2990	0.0126	0.040*
C9	0.07966 (19)	0.2947 (2)	0.16440 (11)	0.0262 (4)
H9	0.0009	0.1934	0.1823	0.031*
C10	0.23260 (19)	0.09109 (19)	0.62683 (10)	0.0195 (3)
H10	0.3180	0.0587	0.5728	0.023*
C11	0.27964 (19)	0.04582 (19)	0.72843 (11)	0.0198 (3)
C12	0.1942 (2)	0.0904 (2)	0.81923 (11)	0.0236 (3)
H12	0.0832	0.1637	0.8288	0.028*
C13	0.3013 (2)	0.0078 (2)	0.89459 (11)	0.0296 (4)
H13	0.2760	0.0144	0.9645	0.036*
C14	0.4493 (2)	−0.0841 (2)	0.84866 (11)	0.0296 (4)
H14	0.5449	−0.1527	0.8815	0.036*
C15	−0.30628 (19)	0.2886 (2)	0.54432 (11)	0.0252 (3)
H15A	−0.3426	0.4167	0.5533	0.038*
H15B	−0.2947	0.2136	0.6101	0.038*
H15C	−0.4002	0.2381	0.5121	0.038*
C16	−0.24885 (19)	0.4392 (2)	0.32005 (11)	0.0256 (3)
H16A	−0.3720	0.4274	0.3581	0.038*
H16B	−0.2471	0.3902	0.2567	0.038*
H16C	−0.2187	0.5701	0.3055	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0179 (6)	0.0373 (7)	0.0224 (6)	0.0019 (4)	−0.0009 (4)	−0.0019 (5)
N1	0.0139 (6)	0.0305 (7)	0.0202 (6)	−0.0005 (5)	−0.0008 (5)	−0.0001 (5)
N2	0.0173 (6)	0.0252 (7)	0.0207 (6)	0.0014 (5)	−0.0024 (5)	−0.0019 (5)
N3	0.0220 (7)	0.0198 (6)	0.0195 (6)	−0.0024 (5)	−0.0030 (5)	−0.0034 (5)
N4	0.0234 (7)	0.0246 (7)	0.0220 (7)	0.0024 (5)	−0.0035 (5)	−0.0029 (5)
C1	0.0210 (8)	0.0206 (7)	0.0205 (7)	0.0000 (6)	−0.0038 (6)	−0.0036 (6)
C2	0.0215 (8)	0.0172 (7)	0.0183 (7)	−0.0006 (6)	−0.0028 (6)	−0.0026 (5)
C3	0.0202 (8)	0.0177 (7)	0.0211 (7)	−0.0011 (6)	−0.0017 (6)	−0.0046 (6)
C4	0.0188 (7)	0.0242 (8)	0.0180 (7)	0.0018 (6)	−0.0018 (5)	−0.0001 (6)
C5	0.0280 (8)	0.0319 (9)	0.0253 (8)	−0.0022 (7)	−0.0035 (6)	−0.0005 (7)
C6	0.0311 (9)	0.0404 (10)	0.0318 (9)	−0.0028 (8)	0.0004 (7)	0.0095 (8)
C7	0.0275 (9)	0.0529 (12)	0.0216 (8)	0.0138 (8)	0.0020 (7)	0.0064 (8)
C8	0.0321 (9)	0.0446 (10)	0.0235 (8)	0.0151 (8)	−0.0099 (7)	−0.0099 (7)
C9	0.0242 (8)	0.0282 (8)	0.0278 (8)	0.0011 (6)	−0.0087 (6)	−0.0057 (7)
C10	0.0213 (8)	0.0169 (7)	0.0200 (7)	−0.0031 (6)	0.0002 (6)	−0.0028 (5)
C11	0.0203 (7)	0.0163 (7)	0.0226 (7)	−0.0015 (6)	−0.0036 (6)	−0.0016 (6)
C12	0.0256 (8)	0.0212 (8)	0.0238 (8)	0.0012 (6)	−0.0022 (6)	−0.0043 (6)
C13	0.0413 (10)	0.0291 (9)	0.0184 (7)	0.0042 (7)	−0.0059 (7)	−0.0037 (6)
C14	0.0353 (9)	0.0303 (9)	0.0231 (8)	0.0051 (7)	−0.0090 (7)	−0.0020 (7)
C15	0.0198 (8)	0.0312 (9)	0.0255 (8)	−0.0013 (6)	−0.0016 (6)	−0.0078 (6)
C16	0.0230 (8)	0.0240 (8)	0.0297 (8)	0.0013 (6)	−0.0086 (6)	−0.0007 (6)

Geometric parameters (Å, º)

O1—C1	1.2612 (16)	C7—C8	1.382 (3)
N1—C1	1.3772 (18)	C7—H7	0.9500
N1—N2	1.3890 (15)	C8—C9	1.391 (2)
N1—C4	1.4268 (17)	C8—H8	0.9500
N2—C3	1.3491 (18)	C9—H9	0.9500
N2—C16	1.4485 (17)	C10—C11	1.4436 (19)
N3—C10	1.2823 (17)	C10—H10	0.9500
N3—C2	1.3991 (17)	C11—C12	1.384 (2)
N4—C14	1.3539 (19)	C12—C13	1.403 (2)
N4—C11	1.3745 (18)	C12—H12	0.9500
N4—H4	0.862 (17)	C13—C14	1.371 (2)
C1—C2	1.4314 (18)	C13—H13	0.9500
C2—C3	1.3764 (19)	C14—H14	0.9500
C3—C15	1.4864 (19)	C15—H15A	0.9800
C4—C9	1.383 (2)	C15—H15B	0.9800
C4—C5	1.383 (2)	C15—H15C	0.9800
C5—C6	1.385 (2)	C16—H16A	0.9800
C5—H5	0.9500	C16—H16B	0.9800
C6—C7	1.381 (2)	C16—H16C	0.9800
C6—H6	0.9500
C1—N1—N2	109.92 (11)	C7—C8—H8	119.8
C1—N1—C4	127.88 (11)	C9—C8—H8	119.8
N2—N1—C4	122.19 (11)	C4—C9—C8	119.07 (15)
C3—N2—N1	107.37 (11)	C4—C9—H9	120.5
C3—N2—C16	128.50 (12)	C8—C9—H9	120.5
N1—N2—C16	121.42 (11)	N3—C10—C11	121.65 (13)
C10—N3—C2	119.48 (12)	N3—C10—H10	119.2
C14—N4—C11	109.54 (13)	C11—C10—H10	119.2
C14—N4—H4	124.5 (12)	N4—C11—C12	107.08 (13)
C11—N4—H4	125.9 (12)	N4—C11—C10	120.75 (13)
O1—C1—N1	122.66 (13)	C12—C11—C10	132.17 (14)
O1—C1—C2	132.03 (13)	C11—C12—C13	107.55 (13)
N1—C1—C2	105.30 (12)	C11—C12—H12	126.2
C3—C2—N3	123.17 (13)	C13—C12—H12	126.2
C3—C2—C1	107.40 (12)	C14—C13—C12	107.33 (13)
N3—C2—C1	129.25 (13)	C14—C13—H13	126.3
N2—C3—C2	109.84 (12)	C12—C13—H13	126.3
N2—C3—C15	121.41 (12)	N4—C14—C13	108.49 (13)
C2—C3—C15	128.74 (13)	N4—C14—H14	125.8
C9—C4—C5	120.85 (14)	C13—C14—H14	125.8
C9—C4—N1	120.31 (13)	C3—C15—H15A	109.5
C5—C4—N1	118.84 (13)	C3—C15—H15B	109.5
C4—C5—C6	119.50 (15)	H15A—C15—H15B	109.5
C4—C5—H5	120.2	C3—C15—H15C	109.5
C6—C5—H5	120.2	H15A—C15—H15C	109.5
C7—C6—C5	120.22 (16)	H15B—C15—H15C	109.5
C7—C6—H6	119.9	N2—C16—H16A	109.5
C5—C6—H6	119.9	N2—C16—H16B	109.5
C6—C7—C8	119.98 (15)	H16A—C16—H16B	109.5
C6—C7—H7	120.0	N2—C16—H16C	109.5
C8—C7—H7	120.0	H16A—C16—H16C	109.5
C7—C8—C9	120.36 (15)	H16B—C16—H16C	109.5
C1—N1—N2—C3	4.12 (15)	C1—N1—C4—C9	118.35 (16)
C4—N1—N2—C3	−175.13 (13)	N2—N1—C4—C9	−62.53 (19)
C1—N1—N2—C16	166.96 (12)	C1—N1—C4—C5	−61.8 (2)
C4—N1—N2—C16	−12.3 (2)	N2—N1—C4—C5	117.32 (15)
N2—N1—C1—O1	177.46 (12)	C9—C4—C5—C6	0.3 (2)
C4—N1—C1—O1	−3.3 (2)	N1—C4—C5—C6	−179.59 (13)
N2—N1—C1—C2	−2.60 (15)	C4—C5—C6—C7	1.2 (2)
C4—N1—C1—C2	176.60 (14)	C5—C6—C7—C8	−1.5 (2)
C10—N3—C2—C3	166.66 (13)	C6—C7—C8—C9	0.4 (2)
C10—N3—C2—C1	−18.9 (2)	C5—C4—C9—C8	−1.3 (2)
O1—C1—C2—C3	−179.91 (15)	N1—C4—C9—C8	178.52 (12)
N1—C1—C2—C3	0.17 (15)	C7—C8—C9—C4	1.0 (2)
O1—C1—C2—N3	5.0 (3)	C2—N3—C10—C11	174.50 (12)
N1—C1—C2—N3	−174.97 (14)	C14—N4—C11—C12	0.41 (16)
N1—N2—C3—C2	−3.98 (15)	C14—N4—C11—C10	−179.76 (13)
C16—N2—C3—C2	−165.21 (13)	N3—C10—C11—N4	172.82 (12)
N1—N2—C3—C15	177.35 (13)	N3—C10—C11—C12	−7.4 (2)
C16—N2—C3—C15	16.1 (2)	N4—C11—C12—C13	−0.41 (16)
N3—C2—C3—N2	177.90 (12)	C10—C11—C12—C13	179.78 (15)
C1—C2—C3—N2	2.39 (15)	C11—C12—C13—C14	0.27 (17)
N3—C2—C3—C15	−3.6 (2)	C11—N4—C14—C13	−0.24 (18)
C1—C2—C3—C15	−179.07 (13)	C12—C13—C14—N4	−0.02 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1^i	0.862 (17)	1.959 (18)	2.8117 (16)	170.3 (17)

Symmetry code: (i) −x+1, −y, −z+1.