3-(5-Ethyl-2-methyl-4-nitro-2H-pyrazole-3-carbonyl)­oxazolidin-2-one

The title compound, C₁₀H₁₂N₄O₅, shows an orthogonal relationship between the five-membered rings.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.064
• wR factor = 0.193
• Data-to-parameter ratio = 8.4

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF007_ALERT_1_A  _diffrn_reflns_number is missing
            Total number of reflections measured.
            The following tests will not be performed.
            REFLG_01,REFLT_01

Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 10 for a
            centrosymmetric structure
            sine(theta)/lambda                0.6497
            Proportion of unique data used    0.5701
            Ratio reflections to parameters   8.3750
PLAT030_ALERT_1_C _diffrn_reflns_number .LE. _reflns_number_total .         ?
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       8.38
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT430_ALERT_2_C Short Inter D...A Contact  O3     ..  N4      ..       2.89 Ang.

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

   3 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
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku and Rigaku/MSC, 2000-2004); 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.

(I)

Crystal data

C10H12N4O5	F(000) = 560
Mr = 268.23	Dx = 1.446 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2yn	Cell parameters from 9126 reflections
a = 15.2175 (3) Å	θ = 1.7–27.5°
b = 5.2970 (1) Å	µ = 0.12 mm^−1
c = 15.8185 (3) Å	T = 293 K
β = 104.893 (4)°	Block, colorless
V = 1232.25 (4) Å^3	0.30 × 0.24 × 0.14 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	Rint = 0.068
Detector resolution: 10.00 pixels mm^-1	θmax = 27.5°
ω scans	h = −19→19
2703 independent reflections	k = −6→6
1541 reflections with F^2 > 2σ(F^2)	l = −20→20

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.064	w = 1/[0.0074Fo^2 + σ(Fo^2)]/(4Fo^2)
wR(F^2) = 0.193	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.38 e Å^−3
1541 reflections	Δρmin = −0.31 e Å^−3
184 parameters

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using reflections with F² > 2.0 σ(F²). 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	0.7832 (2)	0.4240 (6)	0.6271 (2)	0.0776 (9)
O2	0.6775 (2)	0.3917 (5)	0.7024 (2)	0.0684 (8)
O3	0.6433 (2)	−0.1824 (5)	0.4905 (2)	0.0762 (9)
O4	0.5784 (2)	0.3380 (5)	0.3902 (2)	0.0694 (8)
O5	0.6402 (2)	0.5719 (6)	0.3084 (2)	0.0758 (9)
N1	0.6672 (2)	0.1260 (5)	0.5918 (2)	0.0481 (7)
N2	0.8363 (2)	0.0864 (5)	0.4936 (2)	0.0487 (8)
N3	0.8811 (2)	0.2257 (5)	0.4452 (2)	0.0514 (8)
N4	0.6448 (2)	0.4170 (5)	0.3669 (2)	0.0531 (8)
C1	0.7154 (3)	0.3253 (6)	0.6382 (2)	0.053 (1)
C2	0.5977 (3)	0.2385 (8)	0.6982 (3)	0.069 (1)
C3	0.5969 (3)	0.0365 (8)	0.6328 (3)	0.064 (1)
C4	0.6823 (2)	0.0108 (6)	0.5191 (2)	0.0483 (9)
C5	0.7475 (2)	0.1396 (6)	0.4753 (2)	0.0447 (8)
C6	0.7325 (2)	0.3163 (6)	0.4096 (2)	0.0435 (8)
C7	0.8169 (2)	0.3702 (6)	0.3929 (2)	0.0450 (8)
C8	0.8419 (2)	0.5541 (6)	0.3305 (2)	0.054 (1)
C9	0.9430 (3)	0.5555 (9)	0.3338 (3)	0.075 (1)
C10	0.8880 (3)	−0.0840 (8)	0.5609 (3)	0.069 (1)
H(1)	0.6016	0.1651	0.7552	0.084*
H(2)	0.5431	0.3403	0.6806	0.085*
H(3)	0.5384	0.0247	0.5904	0.080*
H(4)	0.6129	−0.1264	0.6605	0.080*
H(5)	0.8081	0.5121	0.2713	0.065*
H(6)	0.8244	0.7211	0.3454	0.065*
H(7)	0.9736	0.6748	0.3771	0.090*
H(8)	0.9518	0.6015	0.2778	0.090*
H(9)	0.9673	0.3898	0.3494	0.090*
H(10)	0.8916	−0.2475	0.5358	0.083*
H(11)	0.8578	−0.0983	0.6070	0.083*
H(12)	0.9482	−0.0186	0.5842	0.083*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.080 (2)	0.081 (2)	0.076 (2)	−0.043 (2)	0.028 (2)	−0.020 (1)
O2	0.082 (2)	0.065 (2)	0.063 (1)	−0.000 (1)	0.027 (1)	−0.009 (1)
O3	0.080 (2)	0.064 (2)	0.093 (2)	−0.031 (1)	0.039 (2)	−0.027 (1)
O4	0.031 (1)	0.080 (2)	0.094 (2)	−0.002 (1)	0.009 (1)	0.004 (1)
O5	0.057 (2)	0.095 (2)	0.070 (2)	0.017 (1)	0.007 (1)	0.024 (2)
N1	0.038 (1)	0.055 (1)	0.053 (2)	−0.011 (1)	0.014 (1)	−0.005 (1)
N2	0.035 (1)	0.056 (2)	0.056 (2)	0.001 (1)	0.012 (1)	0.010 (1)
N3	0.040 (2)	0.058 (2)	0.058 (2)	0.001 (1)	0.015 (1)	0.010 (1)
N4	0.038 (2)	0.056 (2)	0.060 (2)	0.005 (1)	0.003 (1)	−0.005 (1)
C1	0.057 (2)	0.050 (2)	0.052 (2)	−0.006 (2)	0.015 (2)	−0.001 (2)
C2	0.052 (2)	0.084 (3)	0.075 (2)	0.016 (2)	0.026 (2)	0.012 (2)
C3	0.048 (2)	0.084 (3)	0.068 (2)	−0.015 (2)	0.027 (2)	0.000 (2)
C4	0.036 (2)	0.052 (2)	0.057 (2)	−0.006 (1)	0.012 (1)	−0.009 (2)
C5	0.034 (2)	0.049 (2)	0.050 (2)	−0.003 (1)	0.010 (1)	−0.005 (1)
C6	0.034 (2)	0.050 (2)	0.045 (2)	0.002 (1)	0.008 (1)	−0.005 (1)
C7	0.042 (2)	0.049 (2)	0.044 (2)	0.004 (1)	0.010 (1)	0.000 (1)
C8	0.052 (2)	0.059 (2)	0.052 (2)	0.000 (2)	0.013 (2)	0.008 (2)
C9	0.057 (2)	0.094 (3)	0.074 (3)	−0.013 (2)	0.014 (2)	0.031 (2)
C10	0.049 (2)	0.071 (2)	0.086 (3)	0.008 (2)	0.016 (2)	0.029 (2)

Geometric parameters (Å, º)

O1—C1	1.210 (5)	C5—C6	1.373 (4)
O2—C1	1.338 (5)	C6—C7	1.406 (5)
O2—C2	1.448 (5)	C7—C8	1.504 (5)
O3—C4	1.211 (4)	C8—C9	1.526 (6)
O4—N4	1.234 (4)	C2—H(1)	0.9700
O5—N4	1.225 (4)	C2—H(2)	0.9700
N1—C1	1.383 (4)	C3—H(3)	0.9700
N1—C3	1.464 (5)	C3—H(4)	0.9700
N1—C4	1.373 (5)	C8—H(5)	0.9700
N2—N3	1.365 (4)	C8—H(6)	0.9700
N2—C5	1.337 (4)	C9—H(7)	0.9600
N2—C10	1.462 (5)	C9—H(8)	0.9600
N3—C7	1.345 (4)	C9—H(9)	0.9600
N4—C6	1.434 (4)	C10—H(10)	0.9600
C2—C3	1.486 (6)	C10—H(11)	0.9600
C4—C5	1.511 (5)	C10—H(12)	0.9600
C1—O2—C2	109.7 (3)	O5—N4—C6	118.1 (3)
C1—N1—C3	111.1 (3)	O2—C2—H(1)	109.3629
C4—N1—C1	127.1 (3)	O2—C2—H(2)	110.4134
N3—N2—C10	119.3 (3)	N1—C3—H(3)	111.1683
N3—N2—C5	112.7 (2)	N1—C3—H(4)	111.1730
C5—N2—C10	127.8 (3)	N2—C10—H(11)	109.2125
N2—N3—C7	105.4 (3)	N2—C10—H(10)	109.4525
O1—C1—O2	123.1 (3)	N2—C10—H(12)	109.7431
O1—C1—N1	127.5 (4)	H(1)—C2—C3	110.2756
O2—C1—N1	109.3 (3)	H(2)—C2—C3	110.3056
O2—C2—C3	107.0 (3)	C2—C3—H(3)	111.6808
O3—C4—N1	121.2 (4)	C2—C3—H(4)	111.7128
O3—C4—C5	121.7 (3)	H(2)—C2—H(1)	109.4620
N1—C4—C5	117.0 (3)	H(4)—C3—H(3)	109.4595
N2—C5—C4	123.5 (3)	C7—C8—H(5)	108.9052
N2—C5—C6	105.7 (3)	C7—C8—H(6)	107.4644
N4—C6—C5	124.3 (3)	H(5)—C8—C9	108.3213
N4—C6—C7	128.3 (3)	H(6)—C8—C9	108.8706
N1—C3—C2	101.5 (3)	C8—C9—H(7)	109.1520
C4—N1—C3	121.7 (3)	C8—C9—H(9)	108.8801
N3—C7—C6	108.9 (3)	C8—C9—H(8)	110.3790
N3—C7—C8	120.4 (3)	H(6)—C8—H(5)	109.4587
C4—C5—C6	130.8 (3)	H(9)—C9—H(7)	109.4696
C5—C6—C7	107.3 (3)	H(8)—C9—H(7)	109.4740
C6—C7—C8	130.7 (3)	H(9)—C9—H(8)	109.4686
C7—C8—C9	113.8 (3)	H(11)—C10—H(10)	109.4743
O4—N4—C6	117.9 (3)	H(12)—C10—H(10)	109.4724
O4—N4—O5	124.1 (3)	H(12)—C10—H(11)	109.4722