3-[(3-Ethyl-1-methyl-4-nitro-1H-pyrazol-5-yl)carbon­yl]-1H-benzimidazole

In the title compound, C₁₄H₁₃N₅O₃, the dihedral angle formed between the five-membered pyrazole and the benzimidazole ring system is 68.2 (2)°.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.136
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

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Computing details

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: WinGX (Farrugia, 1999); software used to prepare material for publication: CrystalStructure.

3-[(3-Ethyl-1-methyl-4-nitro-1H-pyrazol-5-yl)carbonyl]-1H-benzimidazole

Crystal data

C14H13N5O3	F(000) = 624.00
Mr = 299.29	Dx = 1.420 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 10836 reflections
a = 10.442 (4) Å	θ = 3.3–27.5°
b = 7.873 (4) Å	µ = 0.10 mm^−1
c = 17.380 (5) Å	T = 298 K
β = 101.595 (15)°	Block, colorless
V = 1399.7 (10) Å^3	0.42 × 0.38 × 0.30 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	2413 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.025
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→13
Tmin = 0.959, Tmax = 0.969	k = −10→10
13220 measured reflections	l = −22→22
3200 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.041	w = 1/[0.0021Fo^2 + σ(Fo^2)]/(4Fo^2)
wR(F^2) = 0.136	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.18 e Å^−3
3200 reflections	Δρmin = −0.14 e Å^−3
200 parameters

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
O1	0.16242 (12)	0.60264 (18)	0.30255 (6)	0.0743 (3)
O2	0.24798 (11)	0.94772 (16)	0.43858 (6)	0.0660 (3)
O3	0.40260 (12)	1.13195 (17)	0.44605 (9)	0.0781 (4)
N1	0.26064 (10)	0.55495 (13)	0.42912 (6)	0.0396 (2)
N2	0.34316 (11)	0.49630 (17)	0.55605 (6)	0.0495 (3)
N3	0.35007 (11)	0.99773 (16)	0.42229 (6)	0.0488 (3)
N4	0.54033 (11)	0.80187 (14)	0.29483 (6)	0.0420 (2)
N5	0.44581 (10)	0.68583 (13)	0.29884 (6)	0.0415 (2)
C1	0.25207 (13)	0.62800 (19)	0.35627 (6)	0.0444 (3)
C2	0.35863 (13)	0.58168 (19)	0.49556 (6)	0.0449 (3)
C3	0.22749 (12)	0.40386 (17)	0.53085 (6)	0.0404 (3)
C4	0.16642 (13)	0.29134 (19)	0.57325 (8)	0.0493 (3)
C5	0.05153 (14)	0.21801 (19)	0.53540 (9)	0.0531 (4)
C6	−0.00112 (13)	0.2548 (2)	0.45802 (9)	0.0540 (4)
C7	0.05827 (13)	0.36534 (19)	0.41398 (8)	0.0467 (3)
C8	0.17374 (12)	0.43874 (16)	0.45257 (6)	0.0376 (3)
C9	0.36582 (11)	0.73567 (17)	0.34580 (6)	0.0386 (3)
C10	0.41091 (12)	0.89301 (17)	0.37304 (6)	0.0378 (3)
C11	0.52002 (12)	0.93042 (17)	0.33994 (6)	0.0384 (3)
C12	0.60612 (16)	1.0833 (2)	0.34974 (9)	0.0534 (4)
C13	0.6879 (2)	1.1013 (2)	0.28960 (10)	0.0768 (6)
C14	0.44767 (17)	0.5255 (2)	0.25754 (10)	0.0629 (5)
H2	0.4288	0.6547	0.4960	0.054*
H4	0.2020	0.2664	0.6255	0.059*
H5	0.0085	0.1422	0.5625	0.064*
H6	−0.0794	0.2035	0.4345	0.065*
H7	0.0226	0.3888	0.3616	0.056*
H121	0.5512	1.1832	0.3474	0.064*
H122	0.6638	1.0769	0.4009	0.064*
H131	0.7480	1.0079	0.2938	0.092*
H132	0.6328	1.1016	0.2382	0.092*
H133	0.7358	1.2060	0.2979	0.092*
H141	0.3737	0.4582	0.2637	0.076*
H142	0.5267	0.4653	0.2789	0.076*
H143	0.4438	0.5472	0.2028	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0657 (7)	0.1006 (10)	0.0468 (5)	−0.0395 (6)	−0.0121 (5)	0.0120 (5)
O2	0.0520 (6)	0.0704 (8)	0.0828 (7)	−0.0022 (5)	0.0308 (5)	−0.0131 (5)
O3	0.0683 (8)	0.0631 (8)	0.1071 (9)	−0.0133 (6)	0.0274 (7)	−0.0441 (7)
N1	0.0381 (5)	0.0412 (6)	0.0373 (5)	−0.0055 (4)	0.0023 (4)	0.0001 (4)
N2	0.0512 (7)	0.0524 (7)	0.0415 (5)	−0.0052 (5)	0.0012 (4)	0.0027 (5)
N3	0.0443 (6)	0.0488 (7)	0.0529 (6)	0.0014 (5)	0.0086 (5)	−0.0096 (5)
N4	0.0453 (6)	0.0442 (6)	0.0369 (5)	−0.0029 (5)	0.0088 (4)	0.0007 (4)
N5	0.0484 (6)	0.0390 (6)	0.0365 (5)	−0.0031 (4)	0.0072 (4)	−0.0037 (4)
C1	0.0450 (7)	0.0462 (8)	0.0388 (6)	−0.0091 (5)	0.0011 (5)	0.0009 (5)
C2	0.0415 (7)	0.0479 (8)	0.0413 (6)	−0.0069 (5)	−0.0017 (5)	0.0000 (5)
C3	0.0419 (7)	0.0392 (7)	0.0403 (6)	0.0034 (5)	0.0087 (5)	−0.0030 (5)
C4	0.0565 (8)	0.0465 (8)	0.0475 (7)	0.0054 (6)	0.0167 (6)	0.0043 (5)
C5	0.0541 (8)	0.0429 (8)	0.0673 (9)	−0.0014 (6)	0.0241 (7)	0.0050 (6)
C6	0.0437 (7)	0.0457 (8)	0.0725 (9)	−0.0067 (6)	0.0109 (6)	−0.0019 (7)
C7	0.0441 (7)	0.0428 (7)	0.0506 (7)	−0.0043 (5)	0.0030 (5)	−0.0014 (5)
C8	0.0384 (6)	0.0328 (6)	0.0419 (6)	0.0010 (5)	0.0082 (5)	−0.0018 (4)
C9	0.0393 (6)	0.0411 (7)	0.0334 (5)	−0.0022 (5)	0.0023 (4)	0.0022 (4)
C10	0.0383 (6)	0.0385 (7)	0.0353 (5)	0.0003 (5)	0.0041 (4)	−0.0023 (4)
C11	0.0403 (6)	0.0384 (7)	0.0343 (5)	−0.0016 (5)	0.0025 (4)	0.0031 (4)
C12	0.0554 (8)	0.0452 (8)	0.0589 (8)	−0.0101 (6)	0.0098 (6)	0.0017 (6)
C13	0.0833 (13)	0.0834 (14)	0.0680 (10)	−0.0370 (10)	0.0251 (9)	0.0071 (9)
C14	0.0772 (11)	0.0503 (9)	0.0619 (9)	−0.0054 (8)	0.0158 (8)	−0.0189 (7)

Geometric parameters (Å, º)

O1—C1	1.1986 (15)	C7—C8	1.3830 (17)
O2—N3	1.2219 (17)	C9—C10	1.3751 (18)
O3—N3	1.2236 (17)	C10—C11	1.4069 (19)
N1—C1	1.3771 (16)	C11—C12	1.491 (2)
N1—C2	1.3963 (15)	C12—C13	1.484 (2)
N1—C8	1.4055 (17)	C2—H2	0.930
N2—C2	1.2851 (17)	C4—H4	0.930
N2—C3	1.4028 (16)	C5—H5	0.930
N3—C10	1.4264 (18)	C6—H6	0.930
N4—N5	1.3570 (16)	C7—H7	0.930
N4—C11	1.3232 (17)	C12—H121	0.970
N5—C9	1.3386 (17)	C12—H122	0.970
N5—C14	1.454 (2)	C13—H131	0.960
C1—C9	1.4998 (19)	C13—H132	0.960
C3—C4	1.387 (2)	C13—H133	0.960
C3—C8	1.3909 (16)	C14—H141	0.960
C4—C5	1.3741 (19)	C14—H142	0.960
C5—C6	1.378 (2)	C14—H143	0.960
C6—C7	1.385 (2)
O1···N4^i	3.3933 (16)	O2···H143^vii	2.946
O1···C10^i	3.4182 (16)	O3···H2^iv	2.495
O1···C11^i	3.1152 (15)	O3···H122^iv	3.316
O1···C12^i	3.4509 (17)	N2···H2^vi	2.961
O2···C5^ii	3.599 (2)	N2···H121^iv	3.108
O2···C5^iii	3.501 (2)	N2···H122^iv	3.446
O3···O3^iv	3.2308 (18)	N2···H142^vi	2.932
O3···N2^ii	3.5702 (19)	N3···H122^iv	3.160
O3···N3^iv	3.2517 (16)	N3···H143^vii	3.408
O3···C2^iv	3.3635 (19)	N4···H4^vi	2.820
O3···C3^ii	3.3440 (19)	N4···H7^vii	2.752
O3···C8^ii	3.4158 (18)	N4···H133^viii	3.185
O3···C10^iv	3.3550 (17)	N5···H7^vii	3.287
N2···O3^v	3.5702 (19)	C1···H141^vii	3.425
N2···N4^vi	3.5272 (15)	C2···H2^vi	2.878
N2···N5^vi	3.3225 (14)	C2···H121^iv	3.276
N2···C2^vi	3.4643 (19)	C2···H122^iv	3.269
N2···C14^vi	3.5288 (18)	C3···H6^iii	3.561
N3···O3^iv	3.2517 (16)	C4···H7^iii	3.524
N4···O1^vii	3.3933 (16)	C4···H122^vi	3.381
N4···N2^vi	3.5272 (15)	C4···H131^vi	3.295
N4···C4^vi	3.5143 (16)	C4···H132^ix	3.075
N5···N2^vi	3.3225 (14)	C5···H5^x	3.302
C2···O3^iv	3.3635 (19)	C5···H6^x	3.363
C2···N2^vi	3.4643 (19)	C6···H5^x	3.145
C2···C2^vi	3.196 (2)	C6···H133^xi	3.517
C3···O3^v	3.3440 (19)	C6···H143^i	3.393
C4···N4^vi	3.5143 (16)	C7···H132^i	3.510
C5···O2^v	3.599 (2)	C7···H143^i	3.221
C5···O2^iii	3.501 (2)	C9···H141^vii	3.322
C6···C8^iii	3.551 (2)	C10···H141^vii	3.450
C8···O3^v	3.4158 (18)	C11···H4^vi	3.239
C8···C6^iii	3.551 (2)	C11···H7^vii	3.457
C10···O1^vii	3.4182 (16)	C12···H2^iv	3.460
C10···O3^iv	3.3550 (17)	C12···H4^vi	3.381
C11···O1^vii	3.1152 (15)	C12···H6^xii	3.450
C12···O1^vii	3.4509 (17)	C12···H142^ii	3.292
C14···N2^vi	3.5288 (18)	C13···H4^vi	3.346
O1···H121^i	3.136	C13···H4^xiii	3.068
O1···H132^i	3.022	C13···H6^xii	3.230
O1···H141^vii	3.022	C13···H7^vii	3.495
O1···H142^vii	3.597	C13···H142^ii	3.310
O2···H5^iii	2.767	C13···H142^xiv	3.587
O2···H6^iii	3.308	C14···H7^vii	3.581
O2···H122^iv	2.763	C14···H121^v	3.192
O2···H141^vii	3.490	C14···H131^viii	3.472
C1—N1—C2	126.78 (11)	N4—C11—C10	108.76 (11)
C1—N1—C8	127.74 (10)	N4—C11—C12	121.34 (12)
C2—N1—C8	105.48 (10)	C10—C11—C12	129.90 (12)
C2—N2—C3	104.95 (10)	C11—C12—C13	114.58 (13)
O2—N3—O3	123.57 (14)	N1—C2—H2	123.0
O2—N3—C10	117.86 (12)	N2—C2—H2	123.0
O3—N3—C10	118.57 (12)	C3—C4—H4	121.2
N5—N4—C11	106.24 (11)	C5—C4—H4	121.2
N4—N5—C9	112.54 (10)	C4—C5—H5	119.4
N4—N5—C14	118.49 (12)	C6—C5—H5	119.4
C9—N5—C14	128.85 (12)	C5—C6—H6	118.8
O1—C1—N1	122.88 (14)	C7—C6—H6	118.8
O1—C1—C9	120.88 (12)	C6—C7—H7	122.0
N1—C1—C9	116.16 (10)	C8—C7—H7	122.0
N1—C2—N2	113.95 (12)	C11—C12—H121	108.2
N2—C3—C4	128.65 (10)	C11—C12—H122	108.2
N2—C3—C8	110.84 (11)	C13—C12—H121	108.2
C4—C3—C8	120.51 (11)	C13—C12—H122	108.2
C3—C4—C5	117.68 (12)	H121—C12—H122	109.5
C4—C5—C6	121.18 (14)	C12—C13—H131	109.5
C5—C6—C7	122.44 (13)	C12—C13—H132	109.5
C6—C7—C8	115.98 (12)	C12—C13—H133	109.5
N1—C8—C3	104.78 (9)	H131—C13—H132	109.5
N1—C8—C7	133.02 (11)	H131—C13—H133	109.5
C3—C8—C7	122.21 (12)	H132—C13—H133	109.5
N5—C9—C1	120.98 (11)	N5—C14—H141	109.5
N5—C9—C10	105.16 (11)	N5—C14—H142	109.5
C1—C9—C10	133.80 (12)	N5—C14—H143	109.5
N3—C10—C9	124.36 (12)	H141—C14—H142	109.5
N3—C10—C11	128.27 (11)	H141—C14—H143	109.5
C9—C10—C11	107.29 (11)	H142—C14—H143	109.5
C1—N1—C2—N2	−179.61 (13)	O1—C1—C9—N5	−65.72 (19)
C2—N1—C1—O1	−177.61 (14)	O1—C1—C9—C10	111.08 (17)
C2—N1—C1—C9	5.6 (2)	N1—C1—C9—N5	111.18 (13)
C1—N1—C8—C3	179.38 (13)	N1—C1—C9—C10	−72.02 (19)
C1—N1—C8—C7	−0.9 (2)	N2—C3—C4—C5	178.93 (14)
C8—N1—C1—O1	2.4 (2)	N2—C3—C8—N1	0.70 (14)
C8—N1—C1—C9	−174.47 (12)	N2—C3—C8—C7	−179.08 (12)
C2—N1—C8—C3	−0.65 (14)	C4—C3—C8—N1	−179.71 (12)
C2—N1—C8—C7	179.09 (15)	C4—C3—C8—C7	0.5 (2)
C8—N1—C2—N2	0.42 (16)	C8—C3—C4—C5	−0.6 (2)
C2—N2—C3—C4	179.99 (12)	C3—C4—C5—C6	0.06 (19)
C2—N2—C3—C8	−0.45 (16)	C4—C5—C6—C7	0.6 (2)
C3—N2—C2—N1	0.01 (14)	C5—C6—C7—C8	−0.6 (2)
O2—N3—C10—C9	−3.35 (18)	C6—C7—C8—N1	−179.61 (14)
O2—N3—C10—C11	172.88 (12)	C6—C7—C8—C3	0.1 (2)
O3—N3—C10—C9	176.48 (12)	N5—C9—C10—N3	176.69 (10)
O3—N3—C10—C11	−7.29 (19)	N5—C9—C10—C11	−0.21 (12)
N5—N4—C11—C10	0.32 (12)	C1—C9—C10—N3	−0.5 (2)
N5—N4—C11—C12	−179.93 (10)	C1—C9—C10—C11	−177.37 (12)
C11—N4—N5—C9	−0.48 (12)	N3—C10—C11—N4	−176.81 (11)
C11—N4—N5—C14	−177.01 (10)	N3—C10—C11—C12	3.5 (2)
N4—N5—C9—C1	178.04 (10)	C9—C10—C11—N4	−0.07 (13)
N4—N5—C9—C10	0.43 (12)	C9—C10—C11—C12	−179.79 (12)
C14—N5—C9—C1	−5.88 (18)	N4—C11—C12—C13	16.63 (18)
C14—N5—C9—C10	176.51 (12)	C10—C11—C12—C13	−163.68 (13)

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