4-Methyl­acetophenone [(2-methyl-4-nitro-1H-imidazol-1-yl)acet­yl]hydrazone

In the title mol­ecule, C₁₅H₁₇N₅O₃, the nitro group lies in the plane of the imidazole group, which makes a dihedral angle of 59.9 (2)° with the benzene ring. Inter­molecular N—H...O hydrogen bonds link the mol­ecules into centrosymmetric dimers. The crystal packing is further stabilized by weak C—H...O and C—H...N inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.065
• wR factor = 0.256
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.256
PLAT084_ALERT_2_C High R2 Value ..................................       0.26
PLAT157_ALERT_4_C Non-standard Monoclinic Beta Angle less 90 Deg        89.46 Deg.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C24
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C16
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C23

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   4 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Farrugia, 1999); program(s) used to solve structure: SIR2004 (Burla et al., 2004); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

4-Methylacetophenone [(2-methyl-4-nitro-1H-imidazol-1-yl)acetyl]hydrazone

Crystal data

C15H17N5O3	F(000) = 664
Mr = 315.34	Dx = 1.308 Mg m^−3
Monoclinic, P21/c	Melting point = 524–525 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54180 Å
a = 8.423 (2) Å	Cell parameters from 25 reflections
b = 10.577 (4) Å	θ = 15–25°
c = 17.97 (3) Å	µ = 0.78 mm^−1
β = 89.46 (8)°	T = 298 K
V = 1601 (3) Å^3	Plate, colourless
Z = 4	0.3 × 0.1 × 0.1 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	2512 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.066
Graphite monochromator	θmax = 68.0°, θmin = 4.9°
ω–2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→12
Tmin = 0.799, Tmax = 0.926	l = −21→21
3111 measured reflections	2 standard reflections every 60 min
2902 independent reflections	intensity decay: none

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.256	H-atom parameters constrained
S = 1.14	w = 1/[σ^2(Fo^2) + (0.1295P)^2 + 1.2895P] where P = (Fo^2 + 2Fc^2)/3
2902 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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

	x	y	z	Uiso*/Ueq
O12	0.4591 (4)	1.0360 (2)	0.08760 (15)	0.0761 (10)
O41	−0.0500 (4)	1.2251 (3)	0.2636 (3)	0.1033 (16)
O42	0.1268 (4)	1.3437 (3)	0.31357 (19)	0.0825 (11)
N1	0.3216 (3)	0.9911 (2)	0.21945 (14)	0.0478 (8)
N3	0.3600 (3)	1.1705 (3)	0.27901 (17)	0.0575 (10)
N4	0.0868 (4)	1.2472 (3)	0.28163 (18)	0.0611 (10)
N13	0.4002 (4)	0.8454 (3)	0.03981 (16)	0.0593 (10)
N14	0.3374 (3)	0.7258 (2)	0.05162 (16)	0.0536 (9)
C2	0.4307 (4)	1.0689 (3)	0.25197 (17)	0.0498 (10)
C4	0.2055 (4)	1.1548 (3)	0.26327 (19)	0.0525 (11)
C5	0.1775 (4)	1.0444 (3)	0.22681 (19)	0.0502 (10)
C11	0.3546 (4)	0.8815 (3)	0.17312 (18)	0.0520 (10)
C12	0.4085 (4)	0.9265 (3)	0.09706 (18)	0.0539 (10)
C15	0.3305 (4)	0.6525 (3)	−0.0052 (2)	0.0592 (11)
C16	0.3859 (6)	0.6823 (4)	−0.0796 (2)	0.0804 (18)
C17	0.2593 (4)	0.5240 (3)	0.01097 (19)	0.0585 (11)
C18	0.2877 (5)	0.4236 (4)	−0.0378 (2)	0.0720 (14)
C19	0.2214 (6)	0.3092 (4)	−0.0232 (3)	0.0865 (18)
C20	0.1185 (5)	0.2868 (3)	0.0385 (3)	0.0725 (15)
C21	0.0926 (5)	0.3889 (4)	0.0839 (3)	0.0716 (14)
C22	0.1591 (5)	0.5055 (3)	0.0710 (2)	0.0636 (11)
C23	0.0406 (7)	0.1624 (4)	0.0473 (4)	0.102 (2)
C24	0.6011 (5)	1.0395 (4)	0.2551 (3)	0.0750 (16)
H5	0.08064	1.01301	0.21064	0.0602*
H11A	0.43694	0.83032	0.19555	0.0623*
H11B	0.25981	0.83010	0.16862	0.0623*
H13	0.43347	0.86733	−0.00371	0.0713*
H16A	0.49766	0.69985	−0.07857	0.1201*
H16B	0.36662	0.61165	−0.11181	0.1201*
H16C	0.33021	0.75506	−0.09768	0.1201*
H18	0.35144	0.43504	−0.07978	0.0864*
H19	0.24430	0.24228	−0.05519	0.1041*
H21	0.02693	0.37881	0.12538	0.0861*
H22	0.13630	0.57231	0.10303	0.0765*
H23A	0.07799	0.10611	0.00903	0.1524*
H23B	0.06537	0.12792	0.09519	0.1524*
H23C	−0.07231	0.17239	0.04325	0.1524*
H24A	0.62064	0.95939	0.23157	0.1120*
H24B	0.66027	1.10418	0.22965	0.1120*
H24C	0.63366	1.03557	0.30611	0.1120*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O12	0.124 (2)	0.0447 (14)	0.0592 (15)	−0.0217 (14)	0.0161 (14)	−0.0018 (12)
O41	0.0594 (18)	0.088 (2)	0.162 (4)	0.0102 (15)	0.0142 (19)	−0.026 (2)
O42	0.098 (2)	0.0545 (17)	0.095 (2)	0.0159 (14)	0.0031 (16)	−0.0164 (15)
N1	0.0620 (16)	0.0339 (13)	0.0473 (14)	−0.0063 (11)	0.0037 (11)	−0.0038 (10)
N3	0.0639 (17)	0.0463 (16)	0.0621 (18)	0.0013 (12)	0.0037 (13)	−0.0082 (13)
N4	0.0696 (19)	0.0400 (16)	0.0734 (19)	0.0039 (13)	0.0100 (14)	−0.0011 (14)
N13	0.090 (2)	0.0371 (14)	0.0507 (16)	−0.0131 (13)	0.0103 (14)	−0.0089 (12)
N14	0.0768 (18)	0.0319 (13)	0.0521 (15)	−0.0008 (12)	−0.0010 (13)	0.0007 (11)
C2	0.0651 (18)	0.0395 (16)	0.0449 (16)	−0.0009 (13)	−0.0052 (13)	0.0038 (13)
C4	0.0602 (19)	0.0397 (17)	0.0574 (19)	0.0003 (13)	0.0073 (14)	−0.0028 (14)
C5	0.0524 (17)	0.0400 (16)	0.0579 (18)	−0.0064 (13)	0.0062 (13)	0.0024 (14)
C11	0.070 (2)	0.0378 (16)	0.0482 (17)	−0.0047 (14)	0.0043 (14)	0.0008 (13)
C12	0.078 (2)	0.0329 (16)	0.0507 (18)	−0.0032 (14)	0.0087 (15)	−0.0033 (13)
C15	0.076 (2)	0.0469 (19)	0.0546 (19)	0.0000 (15)	−0.0034 (16)	−0.0097 (15)
C16	0.123 (4)	0.072 (3)	0.046 (2)	−0.012 (2)	0.001 (2)	−0.0156 (18)
C17	0.077 (2)	0.0494 (19)	0.0493 (18)	0.0018 (16)	−0.0131 (16)	−0.0085 (15)
C18	0.097 (3)	0.049 (2)	0.070 (2)	0.0100 (19)	−0.010 (2)	−0.0082 (18)
C19	0.106 (3)	0.051 (2)	0.103 (4)	0.004 (2)	−0.029 (3)	−0.020 (2)
C20	0.099 (3)	0.0332 (18)	0.086 (3)	−0.0009 (17)	−0.036 (2)	−0.0040 (17)
C21	0.092 (3)	0.049 (2)	0.074 (2)	−0.0074 (19)	−0.016 (2)	−0.0005 (19)
C22	0.080 (2)	0.0417 (18)	0.069 (2)	0.0021 (16)	−0.0048 (18)	−0.0064 (16)
C23	0.141 (5)	0.037 (2)	0.128 (4)	−0.011 (2)	−0.040 (4)	0.003 (2)
C24	0.067 (2)	0.068 (3)	0.090 (3)	0.0099 (18)	−0.006 (2)	−0.023 (2)

Geometric parameters (Å, º)

O12—C12	1.245 (4)	C19—C20	1.421 (8)
O41—N4	1.222 (5)	C20—C23	1.478 (6)
O42—N4	1.220 (5)	C20—C21	1.370 (7)
N1—C2	1.369 (5)	C21—C22	1.373 (6)
N1—C5	1.344 (5)	C5—H5	0.9300
N1—C11	1.453 (5)	C11—H11A	0.9700
N3—C2	1.319 (5)	C11—H11B	0.9700
N3—C4	1.345 (5)	C16—H16A	0.9600
N4—C4	1.434 (5)	C16—H16B	0.9600
N13—N14	1.387 (5)	C16—H16C	0.9600
N13—C12	1.342 (5)	C18—H18	0.9300
N14—C15	1.284 (5)	C19—H19	0.9300
N13—H13	0.8600	C21—H21	0.9300
C2—C24	1.470 (6)	C22—H22	0.9300
C4—C5	1.361 (5)	C23—H23A	0.9600
C11—C12	1.513 (5)	C23—H23B	0.9600
C15—C16	1.447 (6)	C23—H23C	0.9600
C15—C17	1.513 (5)	C24—H24A	0.9600
C17—C22	1.377 (6)	C24—H24B	0.9600
C17—C18	1.396 (6)	C24—H24C	0.9600
C18—C19	1.357 (7)
O12···N1	2.670 (6)	C18···H16B	2.4800
O12···C2	2.982 (6)	C19···H16A^viii	3.0100
O12···C24	3.250 (8)	C22···H24C^vii	2.8500
O12···N13^i	2.858 (6)	C24···H11A	2.8200
O12···C16^i	3.256 (7)	H5···O41	2.6700
O41···C11^ii	3.249 (7)	H5···H11B	2.5600
O42···N3	2.753 (6)	H5···H23B^x	2.4100
O42···C5^ii	3.411 (7)	H5···O42^vi	2.5400
O42···C24^iii	3.318 (8)	H11A···N14	2.9400
O12···H16C^i	2.8400	H11A···C24	2.8200
O12···H13^i	2.0300	H11A···H24A	2.1700
O12···H16A^i	2.8200	H11A···N3^vii	2.4500
O41···H5	2.6700	H11B···N14	2.4600
O41···H24B^iv	2.8300	H11B···H5	2.5600
O41···H11B^ii	2.4100	H11B···O41^vi	2.4100
O42···H5^ii	2.5400	H13···C16	2.4200
O42···H24A^iii	2.5800	H13···H16A	2.2900
O42···H19^v	2.7200	H13···H16C	2.2500
N1···O12	2.670 (6)	H13···O12^i	2.0300
N3···O42	2.753 (6)	H13···C12^i	3.0500
N3···C11^iii	3.397 (7)	H16A···N13	2.7500
N13···O12^i	2.858 (6)	H16A···H13	2.2900
N3···H11A^iii	2.4500	H16A···O12^i	2.8200
N3···H18^v	2.7700	H16A···C18^viii	3.0700
N13···H16A	2.7500	H16A···C19^viii	3.0100
N13···H16C	2.7200	H16B···C18	2.4800
N14···H11A	2.9400	H16B···H18	1.9600
N14···H11B	2.4600	H16C···N13	2.7200
N14···H22	2.5200	H16C···H13	2.2500
C2···O12	2.982 (6)	H16C···O12^i	2.8400
C5···O42^vi	3.411 (7)	H16C···H23C^ix	2.4900
C11···O41^vi	3.249 (7)	H18···C16	2.6300
C11···N3^vii	3.397 (7)	H18···H16B	1.9600
C12···C24	3.495 (8)	H18···N3^xi	2.7700
C15···C18^viii	3.411 (8)	H18···C2^xi	3.0900
C16···O12^i	3.256 (7)	H19···H23A	2.3100
C17···C21^ix	3.555 (8)	H19···O42^xi	2.7200
C18···C15^viii	3.411 (8)	H22···N14	2.5200
C21···C17^ix	3.555 (8)	H22···H24C^vii	2.5800
C24···O12	3.250 (8)	H23A···H19	2.3100
C24···C12	3.495 (8)	H23B···C5^xii	2.7000
C24···O42^vii	3.318 (8)	H23B···H5^xii	2.4100
C2···H18^v	3.0900	H23C···C15^ix	2.9400
C5···H23B^x	2.7000	H23C···H16C^ix	2.4900
C11···H24A	2.6200	H24A···C11	2.6200
C12···H13^i	3.0500	H24A···C12	3.0400
C12···H24A	3.0400	H24A···H11A	2.1700
C15···H23C^ix	2.9400	H24A···O42^vii	2.5800
C16···H13	2.4200	H24B···O41^xiii	2.8300
C16···H18	2.6300	H24C···C22^iii	2.8500
C18···H16A^viii	3.0700	H24C···H22^iii	2.5800
C2—N1—C5	108.4 (3)	C17—C22—C21	120.4 (4)
C2—N1—C11	126.8 (3)	N1—C5—H5	128.00
C5—N1—C11	124.0 (3)	C4—C5—H5	128.00
C2—N3—C4	104.9 (3)	N1—C11—H11A	110.00
O41—N4—O42	123.4 (4)	N1—C11—H11B	110.00
O41—N4—C4	117.7 (3)	C12—C11—H11A	110.00
O42—N4—C4	118.9 (3)	C12—C11—H11B	110.00
N14—N13—C12	119.2 (3)	H11A—C11—H11B	108.00
N13—N14—C15	116.7 (3)	C15—C16—H16A	109.00
C12—N13—H13	120.00	C15—C16—H16B	109.00
N14—N13—H13	120.00	C15—C16—H16C	109.00
N1—C2—C24	123.3 (3)	H16A—C16—H16B	109.00
N1—C2—N3	110.2 (3)	H16A—C16—H16C	110.00
N3—C2—C24	126.6 (3)	H16B—C16—H16C	110.00
N3—C4—C5	112.3 (3)	C17—C18—H18	120.00
N4—C4—C5	124.9 (3)	C19—C18—H18	120.00
N3—C4—N4	122.8 (3)	C18—C19—H19	118.00
N1—C5—C4	104.3 (3)	C20—C19—H19	118.00
N1—C11—C12	108.7 (3)	C20—C21—H21	118.00
O12—C12—N13	120.7 (3)	C22—C21—H21	118.00
N13—C12—C11	118.3 (3)	C17—C22—H22	120.00
O12—C12—C11	121.0 (3)	C21—C22—H22	120.00
N14—C15—C17	114.3 (3)	C20—C23—H23A	109.00
C16—C15—C17	119.8 (3)	C20—C23—H23B	110.00
N14—C15—C16	125.9 (3)	C20—C23—H23C	109.00
C18—C17—C22	118.9 (3)	H23A—C23—H23B	110.00
C15—C17—C18	119.8 (3)	H23A—C23—H23C	109.00
C15—C17—C22	121.1 (3)	H23B—C23—H23C	109.00
C17—C18—C19	119.3 (4)	C2—C24—H24A	109.00
C18—C19—C20	123.1 (4)	C2—C24—H24B	109.00
C19—C20—C23	119.9 (4)	C2—C24—H24C	109.00
C19—C20—C21	115.2 (4)	H24A—C24—H24B	109.00
C21—C20—C23	124.8 (5)	H24A—C24—H24C	109.00
C20—C21—C22	123.0 (4)	H24B—C24—H24C	110.00
C5—N1—C2—N3	−0.7 (4)	N13—N14—C15—C17	−179.4 (3)
C5—N1—C2—C24	179.3 (4)	N3—C4—C5—N1	−0.6 (4)
C11—N1—C2—N3	169.1 (3)	N4—C4—C5—N1	177.8 (3)
C11—N1—C2—C24	−11.0 (5)	N1—C11—C12—O12	19.3 (4)
C2—N1—C5—C4	0.7 (4)	N1—C11—C12—N13	−160.6 (3)
C11—N1—C5—C4	−169.4 (3)	N14—C15—C17—C22	23.2 (5)
C2—N1—C11—C12	−75.3 (4)	C16—C15—C17—C18	18.5 (5)
C5—N1—C11—C12	93.0 (4)	N14—C15—C17—C18	−160.5 (3)
C4—N3—C2—N1	0.3 (4)	C16—C15—C17—C22	−157.8 (4)
C4—N3—C2—C24	−179.6 (4)	C15—C17—C18—C19	−179.1 (4)
C2—N3—C4—N4	−178.2 (3)	C22—C17—C18—C19	−2.7 (6)
C2—N3—C4—C5	0.2 (4)	C18—C17—C22—C21	2.2 (6)
O41—N4—C4—N3	178.6 (4)	C15—C17—C22—C21	178.5 (4)
O41—N4—C4—C5	0.4 (6)	C17—C18—C19—C20	2.4 (7)
O42—N4—C4—N3	−0.8 (5)	C18—C19—C20—C23	175.0 (5)
O42—N4—C4—C5	−178.9 (4)	C18—C19—C20—C21	−1.3 (7)
C12—N13—N14—C15	179.2 (3)	C19—C20—C21—C22	0.7 (7)
N14—N13—C12—O12	−177.5 (3)	C23—C20—C21—C22	−175.5 (5)
N14—N13—C12—C11	2.4 (5)	C20—C21—C22—C17	−1.2 (7)
N13—N14—C15—C16	1.7 (5)

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) x−1, y, z; (v) x, −y+3/2, z+1/2; (vi) −x, y−1/2, −z+1/2; (vii) −x+1, y−1/2, −z+1/2; (viii) −x+1, −y+1, −z; (ix) −x, −y+1, −z; (x) x, y+1, z; (xi) x, −y+3/2, z−1/2; (xii) x, y−1, z; (xiii) x+1, y, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13···O12^i	0.86	2.03	2.858 (6)	162
C5—H5···O42^vi	0.93	2.54	3.411 (7)	156
C11—H11A···N3^vii	0.97	2.45	3.397 (7)	165
C11—H11B···O41^vi	0.97	2.41	3.249 (7)	145
C24—H24A···O42^vii	0.96	2.58	3.318 (8)	134

Symmetry codes: (i) −x+1, −y+2, −z; (vi) −x, y−1/2, −z+1/2; (vii) −x+1, y−1/2, −z+1/2.