In the title compound, C14H13N5O3, the dihedral angle formed between the five-membered pyrazole and the benzimidazole ring system is 68.2 (2)°.
Supporting information
CCDC reference: 613736
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.136
- Data-to-parameter ratio = 16.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 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
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
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-1
H-pyrazol-5-yl)carbonyl]-1
H-benzimidazole
top
Crystal data top
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) Å3 | 0.42 × 0.38 × 0.30 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2413 reflections with F2 > 2σ(F2) |
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 top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.041 | w = 1/[0.0021Fo2 + σ(Fo2)]/(4Fo2) |
wR(F2) = 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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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···N4i | 3.3933 (16) | O2···H143vii | 2.946 |
O1···C10i | 3.4182 (16) | O3···H2iv | 2.495 |
O1···C11i | 3.1152 (15) | O3···H122iv | 3.316 |
O1···C12i | 3.4509 (17) | N2···H2vi | 2.961 |
O2···C5ii | 3.599 (2) | N2···H121iv | 3.108 |
O2···C5iii | 3.501 (2) | N2···H122iv | 3.446 |
O3···O3iv | 3.2308 (18) | N2···H142vi | 2.932 |
O3···N2ii | 3.5702 (19) | N3···H122iv | 3.160 |
O3···N3iv | 3.2517 (16) | N3···H143vii | 3.408 |
O3···C2iv | 3.3635 (19) | N4···H4vi | 2.820 |
O3···C3ii | 3.3440 (19) | N4···H7vii | 2.752 |
O3···C8ii | 3.4158 (18) | N4···H133viii | 3.185 |
O3···C10iv | 3.3550 (17) | N5···H7vii | 3.287 |
N2···O3v | 3.5702 (19) | C1···H141vii | 3.425 |
N2···N4vi | 3.5272 (15) | C2···H2vi | 2.878 |
N2···N5vi | 3.3225 (14) | C2···H121iv | 3.276 |
N2···C2vi | 3.4643 (19) | C2···H122iv | 3.269 |
N2···C14vi | 3.5288 (18) | C3···H6iii | 3.561 |
N3···O3iv | 3.2517 (16) | C4···H7iii | 3.524 |
N4···O1vii | 3.3933 (16) | C4···H122vi | 3.381 |
N4···N2vi | 3.5272 (15) | C4···H131vi | 3.295 |
N4···C4vi | 3.5143 (16) | C4···H132ix | 3.075 |
N5···N2vi | 3.3225 (14) | C5···H5x | 3.302 |
C2···O3iv | 3.3635 (19) | C5···H6x | 3.363 |
C2···N2vi | 3.4643 (19) | C6···H5x | 3.145 |
C2···C2vi | 3.196 (2) | C6···H133xi | 3.517 |
C3···O3v | 3.3440 (19) | C6···H143i | 3.393 |
C4···N4vi | 3.5143 (16) | C7···H132i | 3.510 |
C5···O2v | 3.599 (2) | C7···H143i | 3.221 |
C5···O2iii | 3.501 (2) | C9···H141vii | 3.322 |
C6···C8iii | 3.551 (2) | C10···H141vii | 3.450 |
C8···O3v | 3.4158 (18) | C11···H4vi | 3.239 |
C8···C6iii | 3.551 (2) | C11···H7vii | 3.457 |
C10···O1vii | 3.4182 (16) | C12···H2iv | 3.460 |
C10···O3iv | 3.3550 (17) | C12···H4vi | 3.381 |
C11···O1vii | 3.1152 (15) | C12···H6xii | 3.450 |
C12···O1vii | 3.4509 (17) | C12···H142ii | 3.292 |
C14···N2vi | 3.5288 (18) | C13···H4vi | 3.346 |
O1···H121i | 3.136 | C13···H4xiii | 3.068 |
O1···H132i | 3.022 | C13···H6xii | 3.230 |
O1···H141vii | 3.022 | C13···H7vii | 3.495 |
O1···H142vii | 3.597 | C13···H142ii | 3.310 |
O2···H5iii | 2.767 | C13···H142xiv | 3.587 |
O2···H6iii | 3.308 | C14···H7vii | 3.581 |
O2···H122iv | 2.763 | C14···H121v | 3.192 |
O2···H141vii | 3.490 | C14···H131viii | 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. |