1-[5-(4-Fluoro­phen­yl)-1,2-oxazol-3-ylmeth­yl]-2-nitro­imino­imidazolidine

In the title compound, C₁₃H₁₂FN₅O₃, the five-membered imidazolidine ring adopts an envelope conformation. The mol­ecular structure is stabilized by an intra­molecular N—H...O hydrogen bond. The crystal structure shows C—H...O and C—H...N inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.034
• wR factor = 0.095
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT431_ALERT_2_C Short Inter HL..A Contact  F1     ..  N5      ..       2.87 Ang.

   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

   0 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
   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: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL97.

1-[5-(4-Fluorophenyl)-1,2-oxazol-3-ylmethyl]-2-nitroiminoimidazolidine

Crystal data

C13H12FN5O3	F(000) = 632
Mr = 305.28	Dx = 1.516 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8077 reflections
a = 7.8575 (6) Å	θ = 2.3–27.8°
b = 15.6860 (12) Å	µ = 0.12 mm^−1
c = 11.4098 (9) Å	T = 273 K
β = 107.945 (1)°	Block, colorless
V = 1337.88 (18) Å^3	0.20 × 0.17 × 0.12 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2179 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 25.0°, θmin = 2.3°
ω scans	h = −9→9
12586 measured reflections	k = −18→18
2359 independent reflections	l = −13→13

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0516P)^2 + 0.2286P] where P = (Fo^2 + 2Fc^2)/3
2359 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

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.

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

	x	y	z	Uiso*/Ueq
C1	0.33050 (17)	0.05391 (8)	0.55667 (11)	0.0444 (3)
C2	0.41332 (17)	0.12940 (9)	0.58928 (12)	0.0469 (3)
H2	0.4221	0.1739	0.5375	0.056*
C3	0.48336 (16)	0.12646 (8)	0.71801 (11)	0.0440 (3)
C4	0.58928 (17)	0.19505 (9)	0.80099 (11)	0.0468 (3)
H4A	0.7089	0.1961	0.7935	0.056*
H4B	0.5342	0.2497	0.7728	0.056*
C5	0.73856 (19)	0.13065 (10)	1.01243 (13)	0.0563 (4)
H5A	0.8578	0.1532	1.0251	0.068*
H5B	0.7328	0.0729	0.9811	0.068*
C6	0.6876 (2)	0.13392 (11)	1.12987 (13)	0.0620 (4)
H6A	0.6938	0.0779	1.1669	0.074*
H6B	0.7641	0.1728	1.1892	0.074*
C7	0.46446 (16)	0.19587 (8)	0.97356 (11)	0.0423 (3)
C8	0.22879 (16)	0.01793 (8)	0.43773 (11)	0.0442 (3)
C9	0.12968 (19)	−0.05669 (8)	0.42781 (13)	0.0508 (3)
H9	0.1319	−0.0867	0.4985	0.061*
C10	0.0279 (2)	−0.08658 (9)	0.31374 (14)	0.0553 (3)
H10	−0.0387	−0.1364	0.3066	0.066*
C11	0.02799 (19)	−0.04086 (9)	0.21140 (13)	0.0518 (3)
C12	0.1267 (2)	0.03180 (10)	0.21700 (13)	0.0556 (4)
H12	0.1259	0.0606	0.1456	0.067*
C13	0.22723 (19)	0.06117 (9)	0.33105 (12)	0.0515 (3)
H13	0.2949	0.1105	0.3368	0.062*
F1	−0.07395 (13)	−0.06824 (6)	0.09893 (8)	0.0726 (3)
N1	0.44654 (17)	0.05461 (8)	0.76240 (10)	0.0575 (3)
N2	0.60292 (14)	0.18488 (7)	0.92953 (9)	0.0467 (3)
N3	0.50424 (17)	0.16493 (8)	1.08668 (11)	0.0549 (3)
N4	0.31718 (14)	0.23349 (7)	0.89848 (10)	0.0476 (3)
N5	0.17815 (15)	0.24343 (7)	0.94278 (10)	0.0497 (3)
O1	0.34824 (14)	0.00694 (6)	0.65873 (8)	0.0570 (3)
O2	0.03909 (14)	0.27097 (7)	0.86784 (10)	0.0652 (3)
O3	0.18586 (14)	0.22652 (7)	1.05060 (9)	0.0622 (3)
H3N	0.438 (2)	0.1765 (11)	1.1321 (16)	0.068 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0435 (7)	0.0481 (7)	0.0445 (7)	0.0043 (5)	0.0180 (5)	0.0057 (5)
C2	0.0511 (7)	0.0494 (7)	0.0442 (7)	−0.0027 (6)	0.0205 (6)	0.0044 (5)
C3	0.0397 (6)	0.0498 (7)	0.0461 (7)	0.0024 (5)	0.0184 (5)	0.0030 (5)
C4	0.0431 (7)	0.0559 (8)	0.0448 (7)	−0.0017 (6)	0.0186 (5)	0.0014 (6)
C5	0.0464 (7)	0.0658 (9)	0.0545 (8)	0.0075 (6)	0.0124 (6)	0.0073 (7)
C6	0.0538 (8)	0.0789 (10)	0.0486 (8)	0.0017 (7)	0.0091 (6)	0.0099 (7)
C7	0.0457 (7)	0.0422 (6)	0.0402 (6)	−0.0048 (5)	0.0152 (5)	−0.0045 (5)
C8	0.0420 (7)	0.0449 (7)	0.0482 (7)	0.0051 (5)	0.0176 (5)	0.0005 (5)
C9	0.0571 (8)	0.0467 (7)	0.0525 (8)	0.0019 (6)	0.0225 (6)	0.0037 (6)
C10	0.0576 (8)	0.0475 (7)	0.0636 (9)	−0.0048 (6)	0.0230 (7)	−0.0074 (7)
C11	0.0514 (7)	0.0540 (8)	0.0488 (7)	0.0039 (6)	0.0139 (6)	−0.0088 (6)
C12	0.0627 (9)	0.0578 (8)	0.0468 (7)	0.0013 (7)	0.0177 (6)	0.0043 (6)
C13	0.0545 (8)	0.0501 (7)	0.0508 (8)	−0.0045 (6)	0.0175 (6)	0.0013 (6)
F1	0.0819 (6)	0.0736 (6)	0.0555 (5)	−0.0105 (5)	0.0111 (4)	−0.0134 (4)
N1	0.0656 (8)	0.0583 (7)	0.0449 (6)	−0.0074 (6)	0.0115 (5)	0.0048 (5)
N2	0.0415 (6)	0.0575 (7)	0.0415 (6)	0.0021 (5)	0.0136 (4)	0.0021 (5)
N3	0.0541 (7)	0.0697 (8)	0.0435 (6)	0.0022 (6)	0.0192 (5)	0.0041 (5)
N4	0.0451 (6)	0.0534 (6)	0.0481 (6)	0.0043 (5)	0.0197 (5)	0.0001 (5)
N5	0.0491 (6)	0.0505 (6)	0.0529 (7)	0.0011 (5)	0.0209 (5)	−0.0085 (5)
O1	0.0683 (6)	0.0518 (6)	0.0476 (5)	−0.0085 (5)	0.0131 (5)	0.0070 (4)
O2	0.0497 (6)	0.0774 (7)	0.0681 (7)	0.0157 (5)	0.0174 (5)	−0.0048 (5)
O3	0.0637 (6)	0.0769 (7)	0.0549 (6)	0.0047 (5)	0.0314 (5)	−0.0049 (5)

Geometric parameters (Å, º)

C1—C2	1.3472 (19)	C7—N2	1.3426 (16)
C1—O1	1.3484 (15)	C7—N4	1.3455 (16)
C1—C8	1.4597 (18)	C8—C13	1.3901 (18)
C2—C3	1.4015 (18)	C8—C9	1.3911 (19)
C2—H2	0.9300	C9—C10	1.383 (2)
C3—N1	1.3042 (17)	C9—H9	0.9300
C3—C4	1.5036 (18)	C10—C11	1.370 (2)
C4—N2	1.4460 (16)	C10—H10	0.9300
C4—H4A	0.9700	C11—F1	1.3563 (16)
C4—H4B	0.9700	C11—C12	1.369 (2)
C5—N2	1.4604 (17)	C12—C13	1.377 (2)
C5—C6	1.513 (2)	C12—H12	0.9300
C5—H5A	0.9700	C13—H13	0.9300
C5—H5B	0.9700	N1—O1	1.4114 (15)
C6—N3	1.4549 (19)	N3—H3N	0.856 (18)
C6—H6A	0.9700	N4—N5	1.3466 (15)
C6—H6B	0.9700	N5—O2	1.2394 (15)
C7—N3	1.3230 (17)	N5—O3	1.2416 (15)
C2—C1—O1	109.22 (11)	C13—C8—C9	119.06 (12)
C2—C1—C8	132.54 (12)	C13—C8—C1	118.69 (12)
O1—C1—C8	118.23 (11)	C9—C8—C1	122.23 (12)
C1—C2—C3	105.12 (11)	C10—C9—C8	120.58 (13)
C1—C2—H2	127.4	C10—C9—H9	119.7
C3—C2—H2	127.4	C8—C9—H9	119.7
N1—C3—C2	111.90 (12)	C11—C10—C9	118.21 (13)
N1—C3—C4	121.32 (12)	C11—C10—H10	120.9
C2—C3—C4	126.78 (11)	C9—C10—H10	120.9
N2—C4—C3	114.42 (11)	F1—C11—C12	117.95 (13)
N2—C4—H4A	108.7	F1—C11—C10	119.04 (13)
C3—C4—H4A	108.7	C12—C11—C10	123.01 (13)
N2—C4—H4B	108.7	C11—C12—C13	118.32 (13)
C3—C4—H4B	108.7	C11—C12—H12	120.8
H4A—C4—H4B	107.6	C13—C12—H12	120.8
N2—C5—C6	102.37 (11)	C12—C13—C8	120.79 (13)
N2—C5—H5A	111.3	C12—C13—H13	119.6
C6—C5—H5A	111.3	C8—C13—H13	119.6
N2—C5—H5B	111.3	C3—N1—O1	105.19 (10)
C6—C5—H5B	111.3	C7—N2—C4	123.37 (10)
H5A—C5—H5B	109.2	C7—N2—C5	110.26 (10)
N3—C6—C5	102.47 (11)	C4—N2—C5	122.17 (11)
N3—C6—H6A	111.3	C7—N3—C6	111.40 (12)
C5—C6—H6A	111.3	C7—N3—H3N	120.5 (12)
N3—C6—H6B	111.3	C6—N3—H3N	125.8 (11)
C5—C6—H6B	111.3	C7—N4—N5	116.73 (11)
H6A—C6—H6B	109.2	O2—N5—O3	121.44 (11)
N3—C7—N2	110.05 (11)	O2—N5—N4	115.22 (11)
N3—C7—N4	132.87 (12)	O3—N5—N4	123.34 (11)
N2—C7—N4	117.08 (11)	C1—O1—N1	108.58 (10)
O1—C1—C2—C3	−0.10 (14)	C2—C3—N1—O1	0.36 (15)
C8—C1—C2—C3	178.48 (13)	C4—C3—N1—O1	−179.61 (11)
C1—C2—C3—N1	−0.17 (15)	N3—C7—N2—C4	166.45 (12)
C1—C2—C3—C4	179.79 (12)	N4—C7—N2—C4	−12.87 (18)
N1—C3—C4—N2	−15.91 (17)	N3—C7—N2—C5	9.15 (16)
C2—C3—C4—N2	164.13 (12)	N4—C7—N2—C5	−170.17 (11)
N2—C5—C6—N3	17.57 (15)	C3—C4—N2—C7	−70.41 (16)
C2—C1—C8—C13	9.0 (2)	C3—C4—N2—C5	84.27 (15)
O1—C1—C8—C13	−172.52 (11)	C6—C5—N2—C7	−17.03 (15)
C2—C1—C8—C9	−169.17 (14)	C6—C5—N2—C4	−174.65 (12)
O1—C1—C8—C9	9.31 (18)	N2—C7—N3—C6	3.52 (16)
C13—C8—C9—C10	−1.36 (19)	N4—C7—N3—C6	−177.29 (14)
C1—C8—C9—C10	176.80 (12)	C5—C6—N3—C7	−13.81 (17)
C8—C9—C10—C11	0.1 (2)	N3—C7—N4—N5	0.1 (2)
C9—C10—C11—F1	−178.63 (12)	N2—C7—N4—N5	179.27 (11)
C9—C10—C11—C12	1.4 (2)	C7—N4—N5—O2	−173.63 (11)
F1—C11—C12—C13	178.47 (12)	C7—N4—N5—O3	6.32 (18)
C10—C11—C12—C13	−1.5 (2)	C2—C1—O1—N1	0.32 (15)
C11—C12—C13—C8	0.2 (2)	C8—C1—O1—N1	−178.49 (10)
C9—C8—C13—C12	1.2 (2)	C3—N1—O1—C1	−0.41 (15)
C1—C8—C13—C12	−177.03 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O3	0.856 (18)	2.070 (17)	2.594 (2)	119 (1)
C2—H2···O2^i	0.93	2.54	3.368 (2)	149
C2—H2···O3^i	0.93	2.56	3.236 (2)	130
C6—H6A···O1^ii	0.97	2.50	3.346 (2)	146
C6—H6A···N1^ii	0.97	2.60	3.488 (2)	153

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