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In the title compounds, C4H8N2O2, (I), and C5H10N2O2, (II), respectively, the amide groups are rotated out of the central C-C-C plane by ca 76° in (I) and by 70-73° in (II). Compound (I) has crystallographic mirror symmetry perpendicular to the molecular plane.
Supporting information
CCDC references: 150745; 150746
For both compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1990); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.
Crystal data top
C4H8N2O2 | Dx = 1.271 Mg m−3 |
Mr = 116.12 | Mo Kα radiation, λ = 0.7107 Å |
Orthorhombic, Pnma | Cell parameters from 25 reflections |
Hall symbol: -P 2ac 2n | θ = 13.8–14.9° |
a = 9.778 (2) Å | µ = 0.10 mm−1 |
b = 10.879 (2) Å | T = 296 K |
c = 5.706 (2) Å | Prismatic, colorless |
V = 607.0 (2) Å3 | 0.25 × 0.20 × 0.10 mm |
Z = 4 | |
Data collection top
Rigaku AFC-5R diffractometer | Rint = 0.000 |
ω–2θ scans | θmax = 27.5° |
Absorption correction: ψ scan (North et al., 1968) | h = −12→0 |
Tmin = 0.980, Tmax = 0.997 | k = 0→14 |
854 measured reflections | l = 0→7 |
735 independent reflections | 3 standard reflections every 150 reflections |
451 reflections with I > 2σ(I) | intensity decay: 3.5% |
Refinement top
Refinement on F2 | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.040 | w = 1/(σ2(Fo2) + {0.050[Max(Fo2,0) + 2Fc2]/3}2) |
wR(F2) = 0.115 | (Δ/σ)max = 0.002 |
S = 1.15 | Δρmax = 0.35 e Å−3 |
735 reflections | Δρmin = −0.27 e Å−3 |
58 parameters | |
Special details top
Refinement. Refinement using reflections with F2 > 0.0 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 (Å2) top | x | y | z | Uiso*/Ueq | |
O(1) | 0.9258 (1) | 0.1058 (1) | 0.2067 (2) | 0.0596 (4) | |
N(1) | 1.1496 (1) | 0.0804 (2) | 0.1445 (3) | 0.0494 (4) | |
C(1) | 1.0771 (3) | 0.2500 | 0.3921 (4) | 0.0418 (6) | |
C(2) | 1.0452 (1) | 0.1379 (2) | 0.2414 (3) | 0.0402 (4) | |
C(3) | 0.9925 (4) | 0.2500 | 0.6160 (5) | 0.0629 (10) | |
H(1) | 1.238 (2) | 0.102 (2) | 0.170 (4) | 0.068 (6)* | |
H(2) | 1.131 (2) | 0.012 (2) | 0.041 (3) | 0.058 (5)* | |
H(3) | 1.172 (2) | 0.2500 | 0.423 (4) | 0.031 (6)* | |
H(4) | 1.020 (2) | 0.179 (2) | 0.703 (4) | 0.090 (8)* | |
H(5) | 0.899 (4) | 0.2500 | 0.571 (6) | 0.080 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O(1) | 0.0284 (6) | 0.0761 (10) | 0.0741 (9) | −0.0074 (6) | 0.0034 (6) | −0.0253 (7) |
N(1) | 0.0288 (8) | 0.0556 (9) | 0.0637 (9) | 0.0012 (7) | −0.0029 (7) | −0.0114 (8) |
C(1) | 0.035 (1) | 0.050 (1) | 0.041 (1) | 0.0000 | −0.008 (1) | 0.0000 |
C(2) | 0.0305 (7) | 0.0487 (9) | 0.0413 (8) | −0.0015 (7) | −0.0026 (6) | 0.0021 (8) |
C(3) | 0.085 (2) | 0.069 (2) | 0.035 (1) | 0.0000 | 0.000 (1) | 0.0000 |
Geometric parameters (Å, º) top
O(1)—C(2) | 1.235 (2) | C(1)—C(3) | 1.522 (4) |
N(1)—C(2) | 1.319 (2) | C(1)—H(3) | 0.95 (2) |
N(1)—H(1) | 0.90 (2) | C(3)—H(4) | 0.96 (3) |
N(1)—H(2) | 0.96 (2) | C(3)—H(4)i | 0.96 (3) |
C(1)—C(2) | 1.524 (2) | C(3)—H(5) | 0.95 (3) |
C(1)—C(2)i | 1.524 (2) | | |
| | | |
O(1)···N(1)ii | 2.844 (2) | C(2)···H(1)ii | 3.07 (2) |
O(1)···N(1)iii | 2.943 (2) | C(2)···H(4)v | 3.12 (2) |
O(1)···H(3)iv | 3.02 (2) | C(2)···H(4)vi | 3.52 (3) |
O(1)···H(4)v | 3.12 (2) | C(3)···H(1)iv | 3.39 (2) |
O(1)···H(4)vi | 3.18 (3) | C(3)···H(1)ii | 3.39 (2) |
O(1)···H(2)ii | 3.38 (2) | H(1)···H(5)viii | 2.64 (3) |
O(1)···H(1)iii | 3.50 (2) | H(1)···H(2)vii | 2.77 (3) |
N(1)···H(4)v | 3.02 (2) | H(1)···H(4)v | 3.52 (3) |
N(1)···H(2)iii | 3.11 (2) | H(1)···H(4)x | 3.58 (3) |
N(1)···H(2)vii | 3.28 (2) | H(2)···H(2)iii | 2.62 (4) |
N(1)···H(5)viii | 3.30 (3) | H(2)···H(4)v | 2.86 (3) |
N(1)···H(4)vi | 3.38 (3) | H(2)···H(4)vi | 2.94 (3) |
N(1)···H(1)ix | 3.53 (2) | H(2)···H(3)ix | 3.50 (2) |
C(2)···H(2)iii | 2.87 (2) | H(3)···H(5)viii | 3.59 (4) |
| | | |
C(2)—N(1)—H(1) | 123 (1) | O(1)—C(2)—N(1) | 122.1 (2) |
C(2)—N(1)—H(2) | 118 (1) | O(1)—C(2)—C(1) | 120.7 (2) |
H(1)—N(1)—H(2) | 118 (1) | N(1)—C(2)—C(1) | 117.2 (2) |
C(2)—C(1)—C(2)i | 106.2 (2) | C(1)—C(3)—H(4) | 106 (1) |
C(2)—C(1)—C(3) | 111.3 (1) | C(1)—C(3)—H(4)i | 106 (1) |
C(2)—C(1)—H(3) | 107.8 (7) | C(1)—C(3)—H(5) | 107 (2) |
C(2)—C(1)i—C(3) | 111.3 (1) | H(4)—C(3)—H(4)i | 108 (2) |
C(2)—C(1)i—H(3) | 107.8 (7) | H(4)—C(3)—H(5) | 114 (1) |
C(3)—C(1)—H(3) | 112 (1) | H(4)—C(3)i—H(5) | 114 (1) |
| | | |
O(1)—C(2)—C(1)—C(2)i | −76.0 (2) | N(1)—C(2)—C(1)—C(2)i | 101.7 (2) |
O(1)—C(2)—C(1)—C(3) | 45.3 (3) | N(1)—C(2)—C(1)—C(3) | −137.0 (2) |
Symmetry codes: (i) x, −y+1/2, z; (ii) x−1/2, y, −z+1/2; (iii) −x+2, −y, −z; (iv) x−1/2, −y+1/2, −z+1/2; (v) x, y, z−1; (vi) −x+2, −y, −z+1; (vii) −x+5/2, −y, z+1/2; (viii) x+1/2, −y+1/2, −z+1/2; (ix) −x+5/2, −y, z−1/2; (x) x+1/2, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1x | 0.91 (2) | 1.97 (2) | 2.8445 (18) | 162 (2) |
N1—H2···O1iii | 0.97 (2) | 1.99 (2) | 2.943 (2) | 169 (2) |
Symmetry codes: (iii) −x+2, −y, −z; (x) x+1/2, y, −z+1/2. |
Crystal data top
C5H10N2O2 | Dx = 1.264 Mg m−3 |
Mr = 130.15 | Mo Kα radiation, λ = 0.7107 Å |
Monoclinic, P21/n | Cell parameters from 25 reflections |
a = 6.570 (1) Å | θ = 12.8–13.5° |
b = 9.502 (1) Å | µ = 0.10 mm−1 |
c = 11.032 (1) Å | T = 296 K |
β = 96.69 (1)° | Prismatic, colorless |
V = 684.1 (2) Å3 | 0.20 × 0.20 × 0.20 mm |
Z = 4 | |
Data collection top
Rigaku AFC-5R diffractometer | Rint = 0.029 |
ω–2θ scans | θmax = 27.6° |
Absorption correction: ψ scan (North et al., 1968) | h = 0→8 |
Tmin = 0.974, Tmax = 0.998 | k = 0→12 |
1830 measured reflections | l = −14→14 |
1589 independent reflections | 3 standard reflections every 150 reflections |
1077 reflections with I > 2σ(I) | intensity decay: 0.5% |
Refinement top
Refinement on F2 | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.051 | w = 1/(σ2(Fo2) + {0.048[Max(Fo2,0) + 2Fc2]/3}2) |
wR(F2) = 0.120 | (Δ/σ)max = 0.003 |
S = 1.13 | Δρmax = 0.60 e Å−3 |
1589 reflections | Δρmin = −0.27 e Å−3 |
121 parameters | |
Special details top
Refinement. Refinement using reflections with F2 > 0.0 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 (Å2) top | x | y | z | Uiso*/Ueq | |
O(1) | 0.1713 (2) | 0.0756 (1) | 0.4007 (1) | 0.0459 (4) | |
O(2) | 0.1758 (2) | 0.0801 (1) | 0.1223 (1) | 0.0392 (4) | |
N(1) | 0.1488 (3) | −0.1502 (2) | 0.0806 (2) | 0.0404 (5) | |
N(2) | 0.1278 (3) | −0.1549 (2) | 0.4256 (2) | 0.0448 (5) | |
C(1) | 0.3394 (3) | −0.0800 (2) | 0.2716 (2) | 0.0313 (5) | |
C(3) | 0.2053 (3) | −0.0466 (2) | 0.3723 (2) | 0.0315 (5) | |
C(4) | 0.5393 (3) | 0.0029 (3) | 0.2888 (2) | 0.0453 (7) | |
C(5) | 0.6802 (4) | −0.0347 (5) | 0.1951 (3) | 0.076 (1) | |
C(6) | 0.2145 (3) | −0.0436 (2) | 0.1504 (2) | 0.0292 (5) | |
H(1) | 0.193 (3) | −0.238 (3) | 0.098 (2) | 0.056 (7)* | |
H(2) | 0.071 (3) | −0.132 (2) | 0.015 (2) | 0.054 (7)* | |
H(3) | 0.041 (3) | −0.136 (2) | 0.481 (2) | 0.049 (6)* | |
H(4) | 0.161 (4) | −0.238 (3) | 0.406 (2) | 0.059 (7)* | |
H(5) | 0.367 (3) | −0.180 (2) | 0.273 (2) | 0.028 (5)* | |
H(6) | 0.507 (3) | 0.104 (2) | 0.286 (2) | 0.047 (6)* | |
H(7) | 0.602 (4) | −0.022 (2) | 0.368 (2) | 0.062 (7)* | |
H(8) | 0.705 (5) | −0.136 (4) | 0.196 (3) | 0.12 (1)* | |
H(9) | 0.614 (5) | −0.021 (3) | 0.109 (3) | 0.095 (9)* | |
H(10) | 0.799 (5) | 0.021 (3) | 0.208 (3) | 0.082 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O(1) | 0.0621 (9) | 0.0284 (7) | 0.0524 (9) | −0.0017 (7) | 0.0285 (7) | −0.0042 (7) |
O(2) | 0.0446 (8) | 0.0263 (7) | 0.0451 (8) | −0.0002 (6) | −0.0009 (6) | 0.0039 (6) |
N(1) | 0.050 (1) | 0.0300 (9) | 0.0389 (10) | 0.0035 (8) | −0.0029 (8) | −0.0022 (8) |
N(2) | 0.062 (1) | 0.0296 (10) | 0.048 (1) | 0.0005 (9) | 0.0279 (10) | −0.0001 (8) |
C(1) | 0.0341 (10) | 0.0284 (9) | 0.0323 (10) | 0.0040 (8) | 0.0082 (7) | 0.0010 (8) |
C(3) | 0.0347 (10) | 0.0294 (10) | 0.0308 (10) | 0.0006 (8) | 0.0057 (8) | 0.0000 (8) |
C(4) | 0.032 (1) | 0.064 (2) | 0.041 (1) | −0.002 (1) | 0.0041 (9) | 0.001 (1) |
C(5) | 0.037 (1) | 0.120 (3) | 0.076 (2) | −0.005 (2) | 0.023 (1) | −0.006 (2) |
C(6) | 0.0268 (8) | 0.0294 (10) | 0.0332 (10) | 0.0004 (8) | 0.0111 (7) | 0.0019 (8) |
Geometric parameters (Å, º) top
O(1)—C(3) | 1.230 (2) | C(1)—C(4) | 1.524 (3) |
O(2)—C(6) | 1.235 (2) | C(1)—C(6) | 1.525 (3) |
N(1)—C(6) | 1.314 (3) | C(1)—H(5) | 0.96 (2) |
N(1)—H(1) | 0.90 (3) | C(4)—C(5) | 1.508 (4) |
N(1)—H(2) | 0.85 (3) | C(4)—H(6) | 0.98 (2) |
N(2)—C(3) | 1.317 (3) | C(4)—H(7) | 0.95 (3) |
N(2)—H(3) | 0.91 (2) | C(5)—H(8) | 0.98 (4) |
N(2)—H(4) | 0.86 (3) | C(5)—H(9) | 1.00 (3) |
C(1)—C(3) | 1.530 (3) | C(5)—H(10) | 0.96 (3) |
| | | |
O(1)···H(7)i | 2.85 (3) | C(5)···H(2)vi | 3.38 (2) |
O(1)···N(1)ii | 2.858 (2) | C(5)···H(2)xi | 3.55 (2) |
O(1)···N(2)iii | 2.996 (2) | C(6)···H(10)iv | 2.92 (3) |
O(1)···H(5)ii | 3.00 (2) | C(6)···H(2)v | 2.97 (3) |
O(1)···H(10)iv | 3.07 (3) | C(6)···H(4)ii | 3.09 (3) |
O(1)···H(2)ii | 3.33 (3) | C(6)···H(9)vi | 3.24 (3) |
O(1)···H(4)iii | 3.58 (3) | C(6)···H(8)iv | 3.52 (3) |
O(2)···H(5)ii | 2.59 (2) | H(1)···H(3)viii | 3.00 (3) |
O(2)···H(10)iv | 2.79 (3) | H(1)···H(7)vii | 3.37 (3) |
O(2)···N(2)ii | 2.906 (2) | H(1)···H(7)xii | 3.41 (4) |
O(2)···N(1)v | 2.982 (3) | H(1)···H(8)iv | 3.59 (4) |
O(2)···H(9)vi | 3.07 (3) | H(2)···H(2)v | 2.69 (5) |
O(2)···C(1)ii | 3.441 (2) | H(2)···H(10)vi | 2.89 (4) |
O(2)···H(3)ii | 3.54 (2) | H(2)···H(9)vi | 2.98 (4) |
O(2)···H(1)ii | 3.55 (3) | H(2)···H(4)xii | 3.07 (3) |
O(2)···H(1)v | 3.56 (3) | H(2)···H(8)iv | 3.30 (4) |
N(1)···H(6)vii | 3.02 (2) | H(2)···H(10)iv | 3.28 (4) |
N(1)···H(2)v | 3.17 (3) | H(2)···H(5)xii | 3.36 (3) |
N(1)···H(9)vi | 3.19 (3) | H(2)···H(6)vii | 3.42 (3) |
N(1)···H(10)iv | 3.26 (3) | H(2)···H(9)iv | 3.43 (4) |
N(1)···H(8)iv | 3.32 (3) | H(3)···H(3)iii | 2.68 (5) |
N(1)···H(10)vi | 3.47 (3) | H(3)···H(7)i | 3.10 (3) |
N(1)···H(3)viii | 3.55 (2) | H(3)···H(7)iv | 3.19 (3) |
N(2)···H(3)iii | 3.19 (2) | H(3)···H(8)ix | 3.27 (4) |
N(2)···H(7)i | 3.20 (3) | H(3)···H(9)ix | 3.54 (4) |
N(2)···H(6)vii | 3.31 (2) | H(3)···H(10)iv | 3.56 (4) |
N(2)···H(10)iv | 3.45 (3) | H(4)···H(6)vii | 2.72 (3) |
N(2)···H(8)ix | 3.54 (4) | H(4)···H(9)ix | 3.22 (4) |
N(2)···H(8)iv | 3.55 (4) | H(4)···H(9)vii | 3.25 (4) |
N(2)···H(2)x | 3.59 (2) | H(4)···H(8)ix | 3.36 (4) |
C(1)···H(1)ii | 3.56 (3) | H(5)···H(6)vii | 3.22 (3) |
C(3)···H(3)iii | 2.97 (2) | H(5)···H(10)xiii | 3.56 (4) |
C(3)···H(1)ii | 3.01 (3) | H(6)···H(8)xiv | 3.09 (5) |
C(3)···H(7)i | 3.07 (3) | H(7)···H(7)i | 3.39 (5) |
C(3)···H(10)iv | 3.09 (3) | H(8)···H(10)xiii | 3.43 (5) |
C(4)···H(1)ii | 3.22 (2) | H(9)···H(9)vi | 2.72 (7) |
C(4)···H(4)ii | 3.42 (3) | | |
| | | |
C(6)—N(1)—H(1) | 121 (1) | C(1)—C(4)—C(5) | 112.5 (2) |
C(6)—N(1)—H(2) | 117 (1) | C(1)—C(4)—H(6) | 109 (1) |
H(1)—N(1)—H(2) | 120 (2) | C(1)—C(4)—H(7) | 105 (1) |
C(3)—N(2)—H(3) | 117 (1) | C(5)—C(4)—H(6) | 111 (1) |
C(3)—N(2)—H(4) | 119 (1) | C(5)—C(4)—H(7) | 110 (2) |
H(3)—N(2)—H(4) | 123 (2) | H(6)—C(4)—H(7) | 110 (1) |
C(3)—C(1)—C(4) | 111.3 (2) | C(4)—C(5)—H(8) | 112 (2) |
C(3)—C(1)—C(6) | 107.1 (1) | C(4)—C(5)—H(9) | 113 (1) |
C(3)—C(1)—H(5) | 108 (1) | C(4)—C(5)—H(10) | 109 (1) |
C(4)—C(1)—C(6) | 111.1 (2) | H(8)—C(5)—H(9) | 98 (2) |
C(4)—C(1)—H(5) | 110 (1) | H(8)—C(5)—H(10) | 113 (2) |
C(6)—C(1)—H(5) | 108 (1) | H(9)—C(5)—H(10) | 109 (2) |
O(1)—C(3)—N(2) | 122.2 (2) | O(2)—C(6)—N(1) | 122.9 (2) |
O(1)—C(3)—C(1) | 121.2 (2) | O(2)—C(6)—C(1) | 120.7 (2) |
N(2)—C(3)—C(1) | 116.6 (2) | N(1)—C(6)—C(1) | 116.5 (2) |
| | | |
O(1)—C(3)—C(1)—C(4) | 48.4 (2) | N(1)—C(6)—C(1)—C(4) | 129.4 (2) |
O(1)—C(3)—C(1)—C(6) | −73.1 (2) | N(2)—C(3)—C(1)—C(4) | −132.1 (2) |
O(2)—C(6)—C(1)—C(3) | 69.7 (2) | N(2)—C(3)—C(1)—C(6) | 106.4 (2) |
O(2)—C(6)—C(1)—C(4) | −52.0 (2) | C(3)—C(1)—C(4)—C(5) | 176.5 (2) |
N(1)—C(6)—C(1)—C(3) | −108.9 (2) | C(5)—C(4)—C(1)—C(6) | −64.3 (3) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x, −y, −z+1; (iv) x−1, y, z; (v) −x, −y, −z; (vi) −x+1, −y, −z; (vii) −x+1/2, y−1/2, −z+1/2; (viii) x+1/2, −y−1/2, z−1/2; (ix) x−1/2, −y−1/2, z+1/2; (x) x+1/2, −y−1/2, z+1/2; (xi) x+1, y, z; (xii) x−1/2, −y−1/2, z−1/2; (xiii) −x+3/2, y−1/2, −z+1/2; (xiv) −x+3/2, y+1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H4···O2vii | 0.85 (3) | 2.08 (3) | 2.906 (2) | 164 (2) |
N2—H3···O1iii | 0.90 (2) | 2.10 (2) | 2.996 (2) | 175 (2) |
N1—H1···O1vii | 0.90 (3) | 1.98 (3) | 2.859 (2) | 165 (2) |
N1—H2···O2v | 0.85 (2) | 2.14 (2) | 2.982 (2) | 167 (2) |
C1—H5···O2vii | 0.97 (2) | 2.59 (2) | 3.441 (2) | 148 (2) |
Symmetry codes: (iii) −x, −y, −z+1; (v) −x, −y, −z; (vii) −x+1/2, y−1/2, −z+1/2. |
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