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In the title compounds, C
18H
20N
2O
2, (I), and C
14H
11N
3O
4·0.5H
2O, (II), respectively, the oxime groups have an
E configuration. In (I), the molecules exist as polymers bound by intermolecular C—H
O and O—H
N hydrogen bonds around inversion centres. In (II), intermolecular O
W—H
N, O
W—H
O and O—H
O
W interactions stabilize the molecular packing.
Supporting information
CCDC references: 251340; 251341
Compound (I) was prepared as follows. To a solution of 4-tert-butylanilinin (0.15 mol, 2.24 g) in ethanol (10 ml) was added dropwise a solution of ω-chloroisonitrosoacetophenone (2.75 g, 0.015 mol) in ethanol (20 ml). NaHCO3 (1.10 g) was added to the solution. The precipated product was filtered off and the resulting solution was allowed to stand for 1 h at room temperature for crystallization to occur. Compound (II) was prepared from a mixture of w-chloroisonitrosoacetophenone (2.75 g, 0.015 mol) and NaHCO3 (1.10 g, 0.015 mol) in p-nitroanilyn (0.015 mol, 1.38 g) dissolved in ethanol (10 ml). The precipitate was stirred for 4 h and dissolved in water (10 ml). The crystallized product was filtered off, washed with ethanol and dried.
In compound (I), C-bound H atoms were positioned geometrically and refined as a riding model, with C—H distances in the range 0.93–0.96 Å and with Uiso(H) = 1.2Ueq or 1.5Ueq of the parent atom. The remaining H atoms were located by difference Fourier methods and refined with isotropic displacement parameters. In the final stages of refinement for compound (II), the H atoms on O1A, O1B and the phenyl groups were placed in calculated positions and refined using a riding model, with X—H distances of 0.82 and 0.93 Å, respectively, and with Uiso(H) = 1.2Ueq of the parent atom. The water H atoms were disordered and restraints (O—H = 0.82 Å and H—H = 1.30 Å) were applied to them. They were located by difference Fourier methods and refined with isotropic displacement parameters.
For both compounds, data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
(I)
N1-(4-
tert-Butylphenyl)-
N2-hydroxy-
α-oxo-
α-phenylacetamidine
top
Crystal data top
C18H20N2O2 | Z = 2 |
Mr = 296.36 | F(000) = 316 |
Triclinic, P1 | Dx = 1.236 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.4331 (10) Å | Cell parameters from 4848 reflections |
b = 10.7150 (15) Å | θ = 2.0–26.8° |
c = 12.299 (2) Å | µ = 0.08 mm−1 |
α = 75.054 (12)° | T = 293 K |
β = 82.120 (12)° | Rod, yellow |
γ = 77.258 (11)° | 0.42 × 0.19 × 0.05 mm |
V = 796.0 (2) Å3 | |
Data collection top
Stoe IPDS 2 diffractometer | 1403 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.093 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
Detector resolution: 6.67 pixels mm-1 | h = −7→7 |
ϕ scans | k = −12→12 |
10299 measured reflections | l = −14→14 |
2808 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0381P)2] where P = (Fo2 + 2Fc2)/3 |
2808 reflections | (Δ/σ)max < 0.001 |
207 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Crystal data top
C18H20N2O2 | γ = 77.258 (11)° |
Mr = 296.36 | V = 796.0 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.4331 (10) Å | Mo Kα radiation |
b = 10.7150 (15) Å | µ = 0.08 mm−1 |
c = 12.299 (2) Å | T = 293 K |
α = 75.054 (12)° | 0.42 × 0.19 × 0.05 mm |
β = 82.120 (12)° | |
Data collection top
Stoe IPDS 2 diffractometer | 1403 reflections with I > 2σ(I) |
10299 measured reflections | Rint = 0.093 |
2808 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | Δρmax = 0.13 e Å−3 |
2808 reflections | Δρmin = −0.21 e Å−3 |
207 parameters | |
Special details top
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 1.0008 (4) | 0.1449 (2) | 0.4568 (2) | 0.0436 (7) | |
N2 | 0.8023 (5) | 0.3598 (2) | 0.4180 (3) | 0.0495 (8) | |
O1 | 0.8108 (4) | 0.1207 (2) | 0.5250 (2) | 0.0557 (7) | |
O2 | 1.3367 (4) | 0.3021 (2) | 0.3709 (2) | 0.0561 (7) | |
C1 | 0.9814 (5) | 0.2679 (3) | 0.4085 (3) | 0.0375 (8) | |
C2 | 1.1764 (5) | 0.3008 (3) | 0.3307 (3) | 0.0390 (8) | |
C3 | 1.1644 (5) | 0.3210 (3) | 0.2085 (3) | 0.0402 (8) | |
C4 | 0.9908 (6) | 0.2968 (3) | 0.1664 (3) | 0.0518 (9) | |
H4 | 0.8756 | 0.2721 | 0.2155 | 0.062* | |
C5 | 0.9896 (7) | 0.3093 (4) | 0.0524 (3) | 0.0659 (11) | |
H5 | 0.8743 | 0.2921 | 0.0246 | 0.079* | |
C6 | 1.1580 (8) | 0.3472 (4) | −0.0204 (4) | 0.0726 (12) | |
H6 | 1.1560 | 0.3569 | −0.0976 | 0.087* | |
C7 | 1.3293 (7) | 0.3706 (4) | 0.0211 (4) | 0.0732 (12) | |
H7 | 1.4439 | 0.3953 | −0.0285 | 0.088* | |
C8 | 1.3342 (6) | 0.3581 (3) | 0.1344 (3) | 0.0564 (10) | |
H8 | 1.4512 | 0.3745 | 0.1615 | 0.068* | |
C9 | 0.7698 (5) | 0.4966 (3) | 0.3703 (3) | 0.0366 (8) | |
C10 | 0.5712 (5) | 0.5613 (3) | 0.3357 (3) | 0.0492 (9) | |
H10 | 0.4633 | 0.5141 | 0.3419 | 0.059* | |
C11 | 0.5313 (5) | 0.6955 (3) | 0.2921 (3) | 0.0474 (9) | |
H11 | 0.3950 | 0.7368 | 0.2708 | 0.057* | |
C12 | 0.6850 (5) | 0.7710 (3) | 0.2787 (2) | 0.0349 (7) | |
C13 | 0.8820 (5) | 0.7039 (3) | 0.3160 (3) | 0.0416 (8) | |
H13 | 0.9900 | 0.7511 | 0.3100 | 0.050* | |
C14 | 0.9247 (5) | 0.5697 (3) | 0.3617 (3) | 0.0435 (8) | |
H14 | 1.0586 | 0.5288 | 0.3867 | 0.052* | |
C15 | 0.6424 (5) | 0.9203 (3) | 0.2287 (3) | 0.0405 (8) | |
C16 | 0.4223 (6) | 0.9697 (3) | 0.1826 (3) | 0.0654 (11) | |
H16A | 0.4016 | 1.0631 | 0.1519 | 0.098* | |
H16B | 0.3134 | 0.9504 | 0.2426 | 0.098* | |
H16C | 0.4138 | 0.9266 | 0.1244 | 0.098* | |
C17 | 0.8119 (6) | 0.9551 (3) | 0.1315 (3) | 0.0686 (11) | |
H17A | 0.7845 | 1.0485 | 0.1005 | 0.103* | |
H17B | 0.8063 | 0.9106 | 0.0738 | 0.103* | |
H17C | 0.9511 | 0.9281 | 0.1594 | 0.103* | |
C18 | 0.6534 (6) | 0.9902 (3) | 0.3209 (3) | 0.0630 (11) | |
H18A | 0.6272 | 1.0837 | 0.2902 | 0.095* | |
H18B | 0.7927 | 0.9623 | 0.3486 | 0.095* | |
H18C | 0.5471 | 0.9686 | 0.3818 | 0.095* | |
H1N | 0.693 (5) | 0.330 (3) | 0.445 (3) | 0.049 (11)* | |
H1O | 0.836 (6) | 0.031 (4) | 0.545 (3) | 0.098 (15)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0473 (17) | 0.0299 (15) | 0.0480 (17) | −0.0090 (13) | 0.0058 (15) | −0.0029 (13) |
N2 | 0.0443 (18) | 0.0255 (14) | 0.067 (2) | −0.0055 (15) | 0.0125 (17) | −0.0008 (14) |
O1 | 0.0621 (16) | 0.0313 (13) | 0.0611 (16) | −0.0094 (12) | 0.0176 (13) | −0.0003 (12) |
O2 | 0.0463 (14) | 0.0514 (14) | 0.0713 (17) | −0.0130 (12) | −0.0104 (13) | −0.0100 (12) |
C1 | 0.046 (2) | 0.0261 (16) | 0.039 (2) | −0.0059 (15) | −0.0039 (16) | −0.0070 (14) |
C2 | 0.0361 (19) | 0.0209 (15) | 0.057 (2) | −0.0030 (14) | −0.0018 (17) | −0.0064 (15) |
C3 | 0.0453 (19) | 0.0259 (15) | 0.048 (2) | −0.0059 (14) | 0.0010 (17) | −0.0089 (15) |
C4 | 0.058 (2) | 0.0438 (19) | 0.054 (2) | −0.0108 (17) | 0.0034 (19) | −0.0153 (18) |
C5 | 0.088 (3) | 0.056 (2) | 0.060 (3) | −0.018 (2) | −0.006 (2) | −0.021 (2) |
C6 | 0.114 (4) | 0.051 (2) | 0.048 (3) | −0.014 (2) | 0.008 (3) | −0.013 (2) |
C7 | 0.087 (3) | 0.061 (2) | 0.065 (3) | −0.021 (2) | 0.027 (2) | −0.016 (2) |
C8 | 0.061 (2) | 0.047 (2) | 0.061 (3) | −0.0194 (19) | 0.015 (2) | −0.0130 (19) |
C9 | 0.0418 (19) | 0.0237 (15) | 0.042 (2) | −0.0041 (14) | 0.0055 (16) | −0.0096 (14) |
C10 | 0.038 (2) | 0.0328 (18) | 0.074 (3) | −0.0116 (16) | 0.0013 (19) | −0.0084 (17) |
C11 | 0.0358 (19) | 0.0345 (18) | 0.067 (2) | −0.0025 (15) | −0.0071 (18) | −0.0045 (17) |
C12 | 0.0391 (18) | 0.0283 (15) | 0.0358 (19) | −0.0042 (15) | −0.0013 (15) | −0.0078 (14) |
C13 | 0.0398 (19) | 0.0335 (17) | 0.053 (2) | −0.0082 (15) | −0.0074 (17) | −0.0096 (16) |
C14 | 0.0389 (19) | 0.0302 (17) | 0.060 (2) | −0.0025 (15) | −0.0097 (17) | −0.0089 (16) |
C15 | 0.049 (2) | 0.0263 (15) | 0.043 (2) | −0.0049 (14) | −0.0044 (16) | −0.0044 (14) |
C16 | 0.067 (3) | 0.0386 (19) | 0.082 (3) | 0.0006 (18) | −0.026 (2) | 0.0010 (19) |
C17 | 0.081 (3) | 0.044 (2) | 0.070 (3) | −0.014 (2) | 0.011 (2) | 0.0002 (19) |
C18 | 0.083 (3) | 0.0366 (18) | 0.072 (3) | −0.0099 (18) | −0.008 (2) | −0.0178 (19) |
Geometric parameters (Å, º) top
N1—C1 | 1.283 (3) | C10—C11 | 1.378 (4) |
N1—O1 | 1.418 (3) | C10—H10 | 0.9300 |
N2—C1 | 1.354 (4) | C11—C12 | 1.378 (4) |
N2—C9 | 1.411 (4) | C11—H11 | 0.9300 |
N2—H1N | 0.83 (3) | C12—C13 | 1.386 (4) |
O1—H1O | 0.91 (4) | C12—C15 | 1.535 (4) |
O2—C2 | 1.208 (3) | C13—C14 | 1.382 (4) |
C1—C2 | 1.518 (4) | C13—H13 | 0.9300 |
C2—C3 | 1.473 (4) | C14—H14 | 0.9300 |
C3—C8 | 1.383 (4) | C15—C18 | 1.529 (4) |
C3—C4 | 1.392 (4) | C15—C16 | 1.530 (4) |
C4—C5 | 1.375 (5) | C15—C17 | 1.532 (5) |
C4—H4 | 0.9300 | C16—H16A | 0.9600 |
C5—C6 | 1.371 (5) | C16—H16B | 0.9600 |
C5—H5 | 0.9300 | C16—H16C | 0.9600 |
C6—C7 | 1.371 (6) | C17—H17A | 0.9600 |
C6—H6 | 0.9300 | C17—H17B | 0.9600 |
C7—C8 | 1.370 (5) | C17—H17C | 0.9600 |
C7—H7 | 0.9300 | C18—H18A | 0.9600 |
C8—H8 | 0.9300 | C18—H18B | 0.9600 |
C9—C14 | 1.376 (4) | C18—H18C | 0.9600 |
C9—C10 | 1.378 (4) | | |
| | | |
C1—N1—O1 | 110.1 (3) | C10—C11—H11 | 118.7 |
C1—N2—C9 | 128.3 (3) | C12—C11—H11 | 118.7 |
C1—N2—H1N | 115 (2) | C11—C12—C13 | 115.6 (3) |
C9—N2—H1N | 116 (2) | C11—C12—C15 | 122.9 (3) |
N1—O1—H1O | 101 (3) | C13—C12—C15 | 121.5 (3) |
N1—C1—N2 | 124.8 (3) | C14—C13—C12 | 122.7 (3) |
N1—C1—C2 | 113.2 (3) | C14—C13—H13 | 118.6 |
N2—C1—C2 | 121.9 (3) | C12—C13—H13 | 118.6 |
O2—C2—C3 | 122.9 (3) | C9—C14—C13 | 120.2 (3) |
O2—C2—C1 | 119.4 (3) | C9—C14—H14 | 119.9 |
C3—C2—C1 | 117.6 (3) | C13—C14—H14 | 119.9 |
C8—C3—C4 | 119.3 (3) | C18—C15—C16 | 108.8 (3) |
C8—C3—C2 | 119.3 (3) | C18—C15—C17 | 109.3 (3) |
C4—C3—C2 | 121.3 (3) | C16—C15—C17 | 108.1 (3) |
C5—C4—C3 | 120.0 (4) | C18—C15—C12 | 108.9 (3) |
C5—C4—H4 | 120.0 | C16—C15—C12 | 111.9 (3) |
C3—C4—H4 | 120.0 | C17—C15—C12 | 109.8 (3) |
C6—C5—C4 | 120.2 (4) | C15—C16—H16A | 109.5 |
C6—C5—H5 | 119.9 | C15—C16—H16B | 109.5 |
C4—C5—H5 | 119.9 | H16A—C16—H16B | 109.5 |
C5—C6—C7 | 119.8 (4) | C15—C16—H16C | 109.5 |
C5—C6—H6 | 120.1 | H16A—C16—H16C | 109.5 |
C7—C6—H6 | 120.1 | H16B—C16—H16C | 109.5 |
C8—C7—C6 | 121.0 (4) | C15—C17—H17A | 109.5 |
C8—C7—H7 | 119.5 | C15—C17—H17B | 109.5 |
C6—C7—H7 | 119.5 | H17A—C17—H17B | 109.5 |
C7—C8—C3 | 119.7 (4) | C15—C17—H17C | 109.5 |
C7—C8—H8 | 120.2 | H17A—C17—H17C | 109.5 |
C3—C8—H8 | 120.2 | H17B—C17—H17C | 109.5 |
C14—C9—C10 | 118.3 (3) | C15—C18—H18A | 109.5 |
C14—C9—N2 | 122.8 (3) | C15—C18—H18B | 109.5 |
C10—C9—N2 | 118.8 (3) | H18A—C18—H18B | 109.5 |
C11—C10—C9 | 120.5 (3) | C15—C18—H18C | 109.5 |
C11—C10—H10 | 119.7 | H18A—C18—H18C | 109.5 |
C9—C10—H10 | 119.7 | H18B—C18—H18C | 109.5 |
C10—C11—C12 | 122.7 (3) | | |
| | | |
O1—N1—C1—N2 | −2.4 (4) | C2—C3—C8—C7 | 176.6 (3) |
O1—N1—C1—C2 | −178.0 (3) | C1—N2—C9—C14 | −38.1 (5) |
C9—N2—C1—N1 | 178.3 (3) | C1—N2—C9—C10 | 145.2 (3) |
C9—N2—C1—C2 | −6.5 (5) | C14—C9—C10—C11 | 1.0 (5) |
N1—C1—C2—O2 | −74.6 (4) | N2—C9—C10—C11 | 177.9 (3) |
N2—C1—C2—O2 | 109.7 (3) | C9—C10—C11—C12 | 1.2 (5) |
N1—C1—C2—C3 | 101.4 (3) | C10—C11—C12—C13 | −2.3 (5) |
N2—C1—C2—C3 | −74.4 (4) | C10—C11—C12—C15 | 179.1 (3) |
O2—C2—C3—C8 | −7.7 (4) | C11—C12—C13—C14 | 1.2 (5) |
C1—C2—C3—C8 | 176.5 (3) | C15—C12—C13—C14 | 179.8 (3) |
O2—C2—C3—C4 | 168.8 (3) | C10—C9—C14—C13 | −2.0 (5) |
C1—C2—C3—C4 | −7.0 (4) | N2—C9—C14—C13 | −178.8 (3) |
C8—C3—C4—C5 | 0.2 (5) | C12—C13—C14—C9 | 0.9 (5) |
C2—C3—C4—C5 | −176.3 (3) | C11—C12—C15—C18 | 112.9 (3) |
C3—C4—C5—C6 | −0.7 (5) | C13—C12—C15—C18 | −65.6 (4) |
C4—C5—C6—C7 | 1.0 (6) | C11—C12—C15—C16 | −7.3 (4) |
C5—C6—C7—C8 | −0.7 (6) | C13—C12—C15—C16 | 174.2 (3) |
C6—C7—C8—C3 | 0.2 (6) | C11—C12—C15—C17 | −127.4 (3) |
C4—C3—C8—C7 | 0.1 (5) | C13—C12—C15—C17 | 54.1 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···N1i | 0.91 (4) | 1.95 (4) | 2.801 (3) | 155 (4) |
C10—H10···O2ii | 0.93 | 2.50 | 3.351 (4) | 152 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x−1, y, z. |
(II)
N1-(4-nitrophenyl)-
N2-hydroxy-
α-oxo-
α-phenylacetamidine hemihydrate
top
Crystal data top
C14H11N3O4·0.5H2O | F(000) = 1224 |
Mr = 294.27 | Dx = 1.412 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5334 reflections |
a = 6.8298 (5) Å | θ = 1.5–24.0° |
b = 15.5454 (15) Å | µ = 0.11 mm−1 |
c = 26.097 (2) Å | T = 293 K |
β = 92.080 (7)° | Rod, yellow |
V = 2769.0 (4) Å3 | 0.40 × 0.22 × 0.12 mm |
Z = 8 | |
Data collection top
Stoe IPDS 2 diffractometer | 1986 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.067 |
Graphite monochromator | θmax = 25.0°, θmin = 1.5° |
Detector resolution: 6.67 pixels mm-1 | h = −8→7 |
ϕ scans | k = −18→18 |
17727 measured reflections | l = −30→30 |
4876 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.81 | w = 1/[σ2(Fo2) + (0.005P)2] where P = (Fo2 + 2Fc2)/3 |
4876 reflections | (Δ/σ)max < 0.001 |
402 parameters | Δρmax = 0.17 e Å−3 |
3 restraints | Δρmin = −0.13 e Å−3 |
Crystal data top
C14H11N3O4·0.5H2O | V = 2769.0 (4) Å3 |
Mr = 294.27 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.8298 (5) Å | µ = 0.11 mm−1 |
b = 15.5454 (15) Å | T = 293 K |
c = 26.097 (2) Å | 0.40 × 0.22 × 0.12 mm |
β = 92.080 (7)° | |
Data collection top
Stoe IPDS 2 diffractometer | 1986 reflections with I > 2σ(I) |
17727 measured reflections | Rint = 0.067 |
4876 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.036 | 3 restraints |
wR(F2) = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.81 | Δρmax = 0.17 e Å−3 |
4876 reflections | Δρmin = −0.13 e Å−3 |
402 parameters | |
Special details top
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1A | 0.6637 (3) | 0.21335 (12) | 0.06230 (7) | 0.0468 (5) | |
N1B | 1.1720 (3) | 0.48109 (12) | 0.44398 (7) | 0.0450 (5) | |
N2A | 0.3680 (3) | 0.28571 (15) | 0.04058 (9) | 0.0548 (6) | |
N2B | 0.8674 (3) | 0.52025 (14) | 0.40480 (8) | 0.0506 (6) | |
N3A | −0.2515 (4) | 0.51018 (16) | 0.07792 (11) | 0.0755 (8) | |
N3B | 0.3301 (4) | 0.49047 (17) | 0.23707 (10) | 0.0755 (8) | |
O1A | 0.6753 (2) | 0.21744 (9) | 0.00884 (6) | 0.0559 (5) | |
H1A | 0.7758 | 0.1935 | 0.0001 | 0.067* | |
O1B | 1.1814 (2) | 0.57043 (9) | 0.45172 (6) | 0.0578 (5) | |
H1B | 1.2836 | 0.5826 | 0.4675 | 0.069* | |
O2A | 0.2934 (3) | 0.21893 (11) | 0.14050 (6) | 0.0643 (5) | |
O2B | 0.8037 (2) | 0.34278 (10) | 0.42569 (6) | 0.0569 (5) | |
O3A | −0.2412 (3) | 0.55168 (15) | 0.11732 (10) | 0.1268 (10) | |
O3B | 0.3724 (4) | 0.44530 (17) | 0.20195 (8) | 0.1377 (11) | |
O4A | −0.3882 (3) | 0.51435 (16) | 0.04786 (9) | 0.1254 (9) | |
O4B | 0.1757 (3) | 0.52825 (14) | 0.23839 (8) | 0.1041 (8) | |
C1A | 0.5052 (4) | 0.25141 (14) | 0.07535 (9) | 0.0448 (7) | |
C1B | 1.0103 (4) | 0.46190 (14) | 0.41877 (8) | 0.0405 (6) | |
C2A | 0.4609 (4) | 0.23725 (15) | 0.13059 (10) | 0.0482 (7) | |
C2B | 0.9639 (4) | 0.36698 (15) | 0.41305 (9) | 0.0421 (6) | |
C3A | 0.6226 (4) | 0.24078 (15) | 0.17016 (9) | 0.0462 (7) | |
C3B | 1.1074 (4) | 0.30725 (14) | 0.39264 (8) | 0.0385 (6) | |
C4A | 0.7902 (4) | 0.28831 (15) | 0.16430 (9) | 0.0559 (7) | |
H4A | 0.8060 | 0.3188 | 0.1340 | 0.067* | |
C4B | 1.2769 (4) | 0.33354 (15) | 0.37044 (8) | 0.0497 (7) | |
H4B | 1.3065 | 0.3918 | 0.3686 | 0.060* | |
C5A | 0.9361 (4) | 0.29172 (17) | 0.20264 (11) | 0.0646 (8) | |
H5A | 1.0469 | 0.3253 | 0.1982 | 0.078* | |
C5B | 1.4026 (4) | 0.27384 (17) | 0.35089 (10) | 0.0629 (8) | |
H5B | 1.5169 | 0.2918 | 0.3358 | 0.075* | |
C6A | 0.9175 (5) | 0.24537 (18) | 0.24738 (11) | 0.0697 (9) | |
H6A | 1.0158 | 0.2468 | 0.2730 | 0.084* | |
C6B | 1.3594 (4) | 0.18755 (17) | 0.35361 (10) | 0.0672 (8) | |
H6B | 1.4460 | 0.1473 | 0.3410 | 0.081* | |
C7A | 0.7514 (5) | 0.19724 (18) | 0.25344 (10) | 0.0697 (9) | |
H7A | 0.7383 | 0.1651 | 0.2832 | 0.084* | |
C7B | 1.1899 (4) | 0.16057 (16) | 0.37478 (10) | 0.0645 (8) | |
H7B | 1.1599 | 0.1023 | 0.3759 | 0.077* | |
C8A | 0.6031 (4) | 0.19601 (16) | 0.21579 (10) | 0.0607 (8) | |
H8A | 0.4893 | 0.1649 | 0.2211 | 0.073* | |
C8B | 1.0649 (4) | 0.21966 (15) | 0.39429 (9) | 0.0508 (7) | |
H8B | 0.9499 | 0.2012 | 0.4089 | 0.061* | |
C9A | 0.2154 (4) | 0.34336 (15) | 0.04977 (9) | 0.0458 (7) | |
C9B | 0.7353 (4) | 0.51216 (14) | 0.36248 (9) | 0.0413 (6) | |
C10A | 0.0580 (4) | 0.34881 (16) | 0.01453 (9) | 0.0556 (7) | |
H10A | 0.0565 | 0.3151 | −0.0149 | 0.067* | |
C10B | 0.7754 (4) | 0.45955 (15) | 0.32140 (9) | 0.0500 (7) | |
H10B | 0.8924 | 0.4289 | 0.3212 | 0.060* | |
C11A | −0.0958 (4) | 0.40396 (16) | 0.02309 (10) | 0.0569 (8) | |
H11A | −0.2016 | 0.4083 | −0.0002 | 0.068* | |
C11B | 0.6416 (4) | 0.45255 (15) | 0.28064 (9) | 0.0546 (7) | |
H11B | 0.6671 | 0.4164 | 0.2533 | 0.066* | |
C12A | −0.0872 (4) | 0.45233 (16) | 0.06732 (11) | 0.0505 (7) | |
C12B | 0.4720 (4) | 0.49889 (16) | 0.28059 (9) | 0.0493 (7) | |
C13A | 0.0691 (4) | 0.44942 (15) | 0.10171 (9) | 0.0540 (7) | |
H13A | 0.0708 | 0.4839 | 0.1309 | 0.065* | |
C13B | 0.4321 (3) | 0.55364 (15) | 0.31996 (9) | 0.0494 (7) | |
H13B | 0.3172 | 0.5858 | 0.3192 | 0.059* | |
C14A | 0.2233 (4) | 0.39539 (14) | 0.09293 (9) | 0.0504 (7) | |
H14A | 0.3315 | 0.3937 | 0.1156 | 0.061* | |
C14B | 0.5656 (3) | 0.56039 (14) | 0.36105 (8) | 0.0460 (7) | |
H14B | 0.5406 | 0.5977 | 0.3879 | 0.055* | |
H2A | 0.374 (4) | 0.2753 (15) | 0.0101 (8) | 0.059 (9)* | |
H2B | 0.878 (3) | 0.5682 (12) | 0.4206 (7) | 0.036 (7)* | |
O1W | 0.0046 (3) | 0.88833 (12) | 0.01269 (6) | 0.0569 (5) | |
H1W | 0.095 (2) | 0.9175 (13) | 0.0253 (8) | 0.068* | |
H2W | −0.072 (3) | 0.8771 (16) | 0.0346 (7) | 0.068* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1A | 0.0548 (16) | 0.0497 (13) | 0.0363 (13) | −0.0060 (12) | 0.0070 (11) | 0.0029 (11) |
N1B | 0.0436 (14) | 0.0381 (12) | 0.0533 (13) | −0.0019 (11) | −0.0006 (11) | −0.0076 (10) |
N2A | 0.0617 (17) | 0.0602 (16) | 0.0425 (15) | 0.0136 (13) | 0.0020 (14) | −0.0037 (14) |
N2B | 0.0500 (15) | 0.0401 (14) | 0.0606 (15) | 0.0103 (12) | −0.0128 (12) | −0.0183 (12) |
N3A | 0.0561 (19) | 0.0680 (19) | 0.102 (2) | 0.0049 (16) | −0.0020 (18) | 0.0047 (17) |
N3B | 0.078 (2) | 0.079 (2) | 0.0682 (19) | 0.0118 (16) | −0.0214 (18) | −0.0129 (15) |
O1A | 0.0572 (12) | 0.0622 (11) | 0.0492 (11) | 0.0039 (9) | 0.0144 (9) | −0.0071 (9) |
O1B | 0.0509 (12) | 0.0423 (11) | 0.0790 (12) | −0.0025 (9) | −0.0155 (10) | −0.0153 (9) |
O2A | 0.0517 (13) | 0.0718 (13) | 0.0705 (13) | −0.0008 (11) | 0.0164 (11) | 0.0127 (10) |
O2B | 0.0413 (12) | 0.0539 (11) | 0.0763 (13) | −0.0029 (10) | 0.0126 (10) | −0.0085 (9) |
O3A | 0.0913 (19) | 0.129 (2) | 0.159 (2) | 0.0518 (16) | −0.0166 (18) | −0.0615 (19) |
O3B | 0.141 (2) | 0.183 (3) | 0.0850 (17) | 0.0624 (19) | −0.0523 (16) | −0.0738 (18) |
O4A | 0.0701 (16) | 0.162 (2) | 0.143 (2) | 0.0417 (16) | −0.0228 (16) | −0.0105 (18) |
O4B | 0.0893 (18) | 0.1190 (19) | 0.1005 (17) | 0.0293 (15) | −0.0454 (16) | −0.0298 (14) |
C1A | 0.0443 (18) | 0.0406 (16) | 0.0500 (17) | −0.0039 (13) | 0.0065 (15) | 0.0025 (13) |
C1B | 0.0427 (16) | 0.0369 (16) | 0.0422 (15) | 0.0026 (14) | 0.0060 (13) | −0.0059 (12) |
C2A | 0.059 (2) | 0.0375 (15) | 0.0490 (18) | 0.0032 (15) | 0.0125 (16) | 0.0020 (13) |
C2B | 0.0395 (17) | 0.0442 (16) | 0.0424 (16) | −0.0002 (14) | −0.0029 (13) | −0.0043 (12) |
C3A | 0.0522 (18) | 0.0439 (16) | 0.0433 (16) | 0.0035 (14) | 0.0130 (14) | 0.0004 (13) |
C3B | 0.0403 (16) | 0.0383 (16) | 0.0369 (15) | −0.0008 (13) | −0.0003 (13) | −0.0040 (12) |
C4A | 0.061 (2) | 0.0551 (18) | 0.0520 (17) | −0.0036 (16) | 0.0052 (17) | 0.0031 (15) |
C4B | 0.056 (2) | 0.0398 (15) | 0.0535 (17) | −0.0063 (15) | 0.0072 (15) | −0.0035 (14) |
C5A | 0.058 (2) | 0.072 (2) | 0.0642 (19) | −0.0099 (17) | 0.0112 (18) | −0.0082 (17) |
C5B | 0.0533 (19) | 0.0573 (19) | 0.080 (2) | −0.0034 (16) | 0.0320 (15) | −0.0117 (16) |
C6A | 0.067 (2) | 0.087 (2) | 0.055 (2) | 0.0163 (19) | 0.0027 (17) | −0.0100 (18) |
C6B | 0.063 (2) | 0.051 (2) | 0.088 (2) | 0.0092 (16) | 0.0153 (18) | −0.0098 (16) |
C7A | 0.077 (2) | 0.082 (2) | 0.0511 (18) | 0.0087 (19) | 0.0102 (19) | 0.0096 (16) |
C7B | 0.071 (2) | 0.0372 (17) | 0.087 (2) | −0.0005 (16) | 0.0214 (18) | −0.0023 (16) |
C8A | 0.059 (2) | 0.072 (2) | 0.0513 (17) | 0.0014 (15) | 0.0142 (17) | 0.0052 (16) |
C8B | 0.0514 (19) | 0.0427 (16) | 0.0595 (17) | −0.0031 (14) | 0.0170 (14) | 0.0009 (14) |
C9A | 0.0506 (19) | 0.0400 (16) | 0.0470 (17) | −0.0033 (14) | 0.0036 (15) | 0.0024 (14) |
C9B | 0.0437 (16) | 0.0364 (15) | 0.0436 (16) | 0.0004 (13) | −0.0024 (14) | −0.0025 (13) |
C10A | 0.064 (2) | 0.0525 (19) | 0.0500 (17) | −0.0056 (16) | −0.0060 (16) | 0.0013 (14) |
C10B | 0.0486 (18) | 0.0512 (17) | 0.0499 (16) | 0.0118 (14) | −0.0017 (15) | −0.0063 (14) |
C11A | 0.0462 (19) | 0.0561 (18) | 0.068 (2) | −0.0066 (15) | −0.0117 (16) | 0.0157 (16) |
C11B | 0.067 (2) | 0.0564 (18) | 0.0404 (16) | 0.0092 (16) | −0.0007 (16) | −0.0098 (14) |
C12A | 0.0417 (18) | 0.0383 (16) | 0.0717 (19) | 0.0013 (14) | 0.0032 (16) | 0.0074 (15) |
C12B | 0.0515 (18) | 0.0528 (18) | 0.0426 (16) | 0.0023 (14) | −0.0097 (14) | −0.0021 (14) |
C13A | 0.060 (2) | 0.0420 (17) | 0.0601 (17) | 0.0008 (14) | 0.0010 (17) | −0.0032 (14) |
C13B | 0.0397 (17) | 0.0505 (17) | 0.0576 (17) | 0.0070 (13) | −0.0039 (15) | −0.0007 (14) |
C14A | 0.0521 (18) | 0.0442 (16) | 0.0547 (17) | 0.0029 (14) | −0.0030 (15) | −0.0021 (14) |
C14B | 0.0500 (18) | 0.0384 (15) | 0.0495 (16) | 0.0068 (13) | 0.0017 (15) | −0.0078 (12) |
O1W | 0.0444 (13) | 0.0608 (13) | 0.0654 (13) | −0.0065 (10) | −0.0004 (10) | 0.0033 (10) |
Geometric parameters (Å, º) top
N1A—C1A | 1.290 (3) | C5B—C6B | 1.376 (3) |
N1A—O1A | 1.402 (2) | C5B—H5B | 0.9300 |
N1B—C1B | 1.299 (3) | C6A—C7A | 1.373 (3) |
N1B—O1B | 1.4045 (19) | C6A—H6A | 0.9300 |
N2A—C1A | 1.387 (3) | C6B—C7B | 1.366 (3) |
N2A—C9A | 1.402 (3) | C6B—H6B | 0.9300 |
N2A—H2A | 0.82 (2) | C7A—C8A | 1.385 (3) |
N2B—C1B | 1.372 (3) | C7A—H7A | 0.9300 |
N2B—C9B | 1.406 (3) | C7B—C8B | 1.365 (3) |
N2B—H2B | 0.855 (17) | C7B—H7B | 0.9300 |
N3A—O4A | 1.200 (3) | C8A—H8A | 0.9300 |
N3A—O3A | 1.214 (3) | C8B—H8B | 0.9300 |
N3A—C12A | 1.472 (3) | C9A—C14A | 1.386 (3) |
N3B—O3B | 1.198 (3) | C9A—C10A | 1.392 (3) |
N3B—O4B | 1.209 (3) | C9B—C14B | 1.380 (3) |
N3B—C12B | 1.472 (3) | C9B—C10B | 1.384 (3) |
O1A—H1A | 0.8200 | C10A—C11A | 1.380 (3) |
O1B—H1B | 0.8200 | C10A—H10A | 0.9300 |
O2A—C2A | 1.216 (3) | C10B—C11B | 1.381 (3) |
O2B—C2B | 1.214 (3) | C10B—H10B | 0.9300 |
C1A—C2A | 1.500 (3) | C11A—C12A | 1.377 (3) |
C1B—C2B | 1.516 (3) | C11A—H11A | 0.9300 |
C2A—C3A | 1.485 (3) | C11B—C12B | 1.364 (3) |
C2B—C3B | 1.464 (3) | C11B—H11B | 0.9300 |
C3A—C4A | 1.376 (3) | C12A—C13A | 1.370 (3) |
C3A—C8A | 1.390 (3) | C12B—C13B | 1.369 (3) |
C3B—C4B | 1.375 (3) | C13A—C14A | 1.373 (3) |
C3B—C8B | 1.393 (3) | C13A—H13A | 0.9300 |
C4A—C5A | 1.387 (3) | C13B—C14B | 1.386 (3) |
C4A—H4A | 0.9300 | C13B—H13B | 0.9300 |
C4B—C5B | 1.375 (3) | C14A—H14A | 0.9300 |
C4B—H4B | 0.9300 | C14B—H14B | 0.9300 |
C5A—C6A | 1.382 (3) | O1W—H1W | 0.823 (9) |
C5A—H5A | 0.9300 | O1W—H2W | 0.809 (9) |
| | | |
C1A—N1A—O1A | 108.68 (19) | C5B—C6B—H6B | 119.8 |
C1B—N1B—O1B | 109.47 (18) | C6A—C7A—C8A | 120.8 (3) |
C1A—N2A—C9A | 128.5 (2) | C6A—C7A—H7A | 119.6 |
C1A—N2A—H2A | 120.2 (18) | C8A—C7A—H7A | 119.6 |
C9A—N2A—H2A | 111.2 (18) | C8B—C7B—C6B | 119.6 (3) |
C1B—N2B—C9B | 125.4 (2) | C8B—C7B—H7B | 120.2 |
C1B—N2B—H2B | 113.6 (13) | C6B—C7B—H7B | 120.2 |
C9B—N2B—H2B | 120.0 (13) | C7A—C8A—C3A | 120.7 (3) |
O4A—N3A—O3A | 123.0 (3) | C7A—C8A—H8A | 119.6 |
O4A—N3A—C12A | 119.4 (3) | C3A—C8A—H8A | 119.6 |
O3A—N3A—C12A | 117.6 (3) | C7B—C8B—C3B | 120.8 (2) |
O3B—N3B—O4B | 122.8 (3) | C7B—C8B—H8B | 119.6 |
O3B—N3B—C12B | 118.2 (3) | C3B—C8B—H8B | 119.6 |
O4B—N3B—C12B | 119.0 (3) | C14A—C9A—C10A | 120.5 (3) |
N1A—O1A—H1A | 109.5 | C14A—C9A—N2A | 120.3 (2) |
N1B—O1B—H1B | 109.5 | C10A—C9A—N2A | 119.1 (2) |
N1A—C1A—N2A | 123.8 (2) | C14B—C9B—C10B | 119.3 (2) |
N1A—C1A—C2A | 112.7 (2) | C14B—C9B—N2B | 119.1 (2) |
N2A—C1A—C2A | 122.0 (2) | C10B—C9B—N2B | 121.5 (2) |
N1B—C1B—N2B | 124.5 (2) | C11A—C10A—C9A | 120.3 (3) |
N1B—C1B—C2B | 116.4 (2) | C11A—C10A—H10A | 119.8 |
N2B—C1B—C2B | 118.2 (2) | C9A—C10A—H10A | 119.8 |
O2A—C2A—C3A | 122.8 (2) | C11B—C10B—C9B | 120.0 (2) |
O2A—C2A—C1A | 117.6 (2) | C11B—C10B—H10B | 120.0 |
C3A—C2A—C1A | 119.5 (2) | C9B—C10B—H10B | 120.0 |
O2B—C2B—C3B | 121.6 (2) | C12A—C11A—C10A | 117.7 (2) |
O2B—C2B—C1B | 117.5 (2) | C12A—C11A—H11A | 121.1 |
C3B—C2B—C1B | 120.8 (2) | C10A—C11A—H11A | 121.1 |
C4A—C3A—C8A | 118.0 (2) | C12B—C11B—C10B | 119.8 (2) |
C4A—C3A—C2A | 122.9 (2) | C12B—C11B—H11B | 120.1 |
C8A—C3A—C2A | 119.0 (3) | C10B—C11B—H11B | 120.1 |
C4B—C3B—C8B | 118.9 (2) | C13A—C12A—C11A | 122.7 (3) |
C4B—C3B—C2B | 123.3 (2) | C13A—C12A—N3A | 118.6 (3) |
C8B—C3B—C2B | 117.7 (2) | C11A—C12A—N3A | 118.8 (3) |
C3A—C4A—C5A | 121.3 (2) | C11B—C12B—C13B | 121.3 (2) |
C3A—C4A—H4A | 119.4 | C11B—C12B—N3B | 119.3 (2) |
C5A—C4A—H4A | 119.4 | C13B—C12B—N3B | 119.4 (2) |
C3B—C4B—C5B | 120.1 (2) | C12A—C13A—C14A | 119.7 (3) |
C3B—C4B—H4B | 119.9 | C12A—C13A—H13A | 120.2 |
C5B—C4B—H4B | 119.9 | C14A—C13A—H13A | 120.2 |
C6A—C5A—C4A | 120.2 (3) | C12B—C13B—C14B | 119.0 (2) |
C6A—C5A—H5A | 119.9 | C12B—C13B—H13B | 120.5 |
C4A—C5A—H5A | 119.9 | C14B—C13B—H13B | 120.5 |
C4B—C5B—C6B | 120.0 (3) | C13A—C14A—C9A | 119.0 (2) |
C4B—C5B—H5B | 120.0 | C13A—C14A—H14A | 120.5 |
C6B—C5B—H5B | 120.0 | C9A—C14A—H14A | 120.5 |
C7A—C6A—C5A | 118.9 (3) | C9B—C14B—C13B | 120.5 (2) |
C7A—C6A—H6A | 120.5 | C9B—C14B—H14B | 119.7 |
C5A—C6A—H6A | 120.5 | C13B—C14B—H14B | 119.7 |
C7B—C6B—C5B | 120.5 (3) | H1W—O1W—H2W | 109.3 (19) |
C7B—C6B—H6B | 119.8 | | |
| | | |
O1A—N1A—C1A—N2A | 3.1 (3) | C2A—C3A—C8A—C7A | 179.5 (2) |
O1A—N1A—C1A—C2A | 169.90 (17) | C6B—C7B—C8B—C3B | 0.3 (4) |
C9A—N2A—C1A—N1A | −165.0 (2) | C4B—C3B—C8B—C7B | 0.7 (4) |
C9A—N2A—C1A—C2A | 29.4 (4) | C2B—C3B—C8B—C7B | 178.4 (2) |
O1B—N1B—C1B—N2B | −3.5 (3) | C1A—N2A—C9A—C14A | 21.8 (4) |
O1B—N1B—C1B—C2B | −172.33 (18) | C1A—N2A—C9A—C10A | −159.4 (2) |
C9B—N2B—C1B—N1B | 153.1 (2) | C1B—N2B—C9B—C14B | 161.0 (2) |
C9B—N2B—C1B—C2B | −38.2 (3) | C1B—N2B—C9B—C10B | −21.6 (4) |
N1A—C1A—C2A—O2A | −134.7 (2) | C14A—C9A—C10A—C11A | −2.4 (4) |
N2A—C1A—C2A—O2A | 32.4 (3) | N2A—C9A—C10A—C11A | 178.9 (2) |
N1A—C1A—C2A—C3A | 41.7 (3) | C14B—C9B—C10B—C11B | −3.1 (4) |
N2A—C1A—C2A—C3A | −151.3 (2) | N2B—C9B—C10B—C11B | 179.4 (2) |
N1B—C1B—C2B—O2B | 127.7 (2) | C9A—C10A—C11A—C12A | −0.2 (4) |
N2B—C1B—C2B—O2B | −41.9 (3) | C9B—C10B—C11B—C12B | 1.3 (4) |
N1B—C1B—C2B—C3B | −52.7 (3) | C10A—C11A—C12A—C13A | 2.0 (4) |
N2B—C1B—C2B—C3B | 137.7 (2) | C10A—C11A—C12A—N3A | −178.6 (2) |
O2A—C2A—C3A—C4A | −156.7 (3) | O4A—N3A—C12A—C13A | 179.0 (3) |
C1A—C2A—C3A—C4A | 27.1 (4) | O3A—N3A—C12A—C13A | −1.1 (4) |
O2A—C2A—C3A—C8A | 21.6 (4) | O4A—N3A—C12A—C11A | −0.4 (4) |
C1A—C2A—C3A—C8A | −154.5 (2) | O3A—N3A—C12A—C11A | 179.5 (3) |
O2B—C2B—C3B—C4B | 169.3 (2) | C10B—C11B—C12B—C13B | 1.0 (4) |
C1B—C2B—C3B—C4B | −10.2 (3) | C10B—C11B—C12B—N3B | −179.6 (2) |
O2B—C2B—C3B—C8B | −8.2 (3) | O3B—N3B—C12B—C11B | −2.8 (4) |
C1B—C2B—C3B—C8B | 172.3 (2) | O4B—N3B—C12B—C11B | 176.3 (3) |
C8A—C3A—C4A—C5A | 0.0 (4) | O3B—N3B—C12B—C13B | 176.5 (3) |
C2A—C3A—C4A—C5A | 178.4 (2) | O4B—N3B—C12B—C13B | −4.3 (4) |
C8B—C3B—C4B—C5B | −0.8 (4) | C11A—C12A—C13A—C14A | −1.2 (4) |
C2B—C3B—C4B—C5B | −178.3 (2) | N3A—C12A—C13A—C14A | 179.4 (2) |
C3A—C4A—C5A—C6A | 1.5 (4) | C11B—C12B—C13B—C14B | −1.3 (4) |
C3B—C4B—C5B—C6B | −0.2 (4) | N3B—C12B—C13B—C14B | 179.3 (2) |
C4A—C5A—C6A—C7A | −1.0 (4) | C12A—C13A—C14A—C9A | −1.4 (4) |
C4B—C5B—C6B—C7B | 1.3 (4) | C10A—C9A—C14A—C13A | 3.1 (4) |
C5A—C6A—C7A—C8A | −1.0 (4) | N2A—C9A—C14A—C13A | −178.1 (2) |
C5B—C6B—C7B—C8B | −1.4 (4) | C10B—C9B—C14B—C13B | 2.8 (4) |
C6A—C7A—C8A—C3A | 2.6 (4) | N2B—C9B—C14B—C13B | −179.7 (2) |
C4A—C3A—C8A—C7A | −2.0 (4) | C12B—C13B—C14B—C9B | −0.6 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O1Wi | 0.82 | 2.00 | 2.808 (3) | 167 |
O1B—H1B···O1Wii | 0.82 | 1.93 | 2.750 (2) | 173 |
O1W—H1W···N1Biii | 0.82 (2) | 2.02 (2) | 2.838 (2) | 176 (2) |
O1W—H2W···O2Biv | 0.81 (2) | 2.00 (2) | 2.787 (2) | 166 (2) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+3/2, −y+3/2, z+1/2; (iii) −x+3/2, y+1/2, −z+1/2; (iv) −x+1/2, y+1/2, −z+1/2. |
Experimental details
| (I) | (II) |
Crystal data |
Chemical formula | C18H20N2O2 | C14H11N3O4·0.5H2O |
Mr | 296.36 | 294.27 |
Crystal system, space group | Triclinic, P1 | Monoclinic, P21/n |
Temperature (K) | 293 | 293 |
a, b, c (Å) | 6.4331 (10), 10.7150 (15), 12.299 (2) | 6.8298 (5), 15.5454 (15), 26.097 (2) |
α, β, γ (°) | 75.054 (12), 82.120 (12), 77.258 (11) | 90, 92.080 (7), 90 |
V (Å3) | 796.0 (2) | 2769.0 (4) |
Z | 2 | 8 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.08 | 0.11 |
Crystal size (mm) | 0.42 × 0.19 × 0.05 | 0.40 × 0.22 × 0.12 |
|
Data collection |
Diffractometer | Stoe IPDS 2 diffractometer | Stoe IPDS 2 diffractometer |
Absorption correction | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10299, 2808, 1403 | 17727, 4876, 1986 |
Rint | 0.093 | 0.067 |
(sin θ/λ)max (Å−1) | 0.595 | 0.595 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.114, 0.95 | 0.036, 0.047, 0.81 |
No. of reflections | 2808 | 4876 |
No. of parameters | 207 | 402 |
No. of restraints | 0 | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.13, −0.21 | 0.17, −0.13 |
Hydrogen-bond geometry (Å, º) for (I) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···N1i | 0.91 (4) | 1.95 (4) | 2.801 (3) | 155 (4) |
C10—H10···O2ii | 0.93 | 2.50 | 3.351 (4) | 152 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x−1, y, z. |
Hydrogen-bond geometry (Å, º) for (II) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O1Wi | 0.82 | 2.00 | 2.808 (3) | 167 |
O1B—H1B···O1Wii | 0.82 | 1.93 | 2.750 (2) | 173 |
O1W—H1W···N1Biii | 0.82 (2) | 2.02 (2) | 2.838 (2) | 176 (2) |
O1W—H2W···O2Biv | 0.81 (2) | 2.00 (2) | 2.787 (2) | 166 (2) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+3/2, −y+3/2, z+1/2; (iii) −x+3/2, y+1/2, −z+1/2; (iv) −x+1/2, y+1/2, −z+1/2. |
Comparison of geometric parameters (Å, °) for (I) and (II) with those in the related compounds (III) and (VI) topBond | (I) | (IIA) | (IIB) | (III) | (IV) |
C1—N1 | 1.283 (3) | 1.290 (3) | 1.299 (3) | 1.288 (2) | 1.295 (3) |
N1—O1 | 1.418 (3) | 1.402 (2) | 1.404 (2) | 1.4093 (18) | 1.413 (3) |
C2—C1 | 1.518 (4) | 1.500 (3) | 1.516 (3) | 1.501 (2) | 1.494 (4) |
| | | | | |
C1—N1—O1 | 110.1 (3) | 108.68 (19) | 109.47 (18) | 111.51 (13) | 109.97 (19) |
C2—C1—N1 | 113.2 (3) | 112.7 (2) | 116.4 (2) | 113.21 (15) | 115.6 (2) |
| | | | | |
C2—C1—N1—O1 | -178.0 (3) | 169.90 (17) | -172.33 (18) | 169.11 (14) | -174.6 (2) |
| | | | | |
A(O1/N1/C1)/B(C3-C8) | 82.8 (3) | 60.3 (2) | 56.6 (2) | 58.61 (10) | 50.10 (14) |
A(O1/N1/C1)/C(C9-C14) | 39.7 (3) | 35.2 (2) | 44.6 (2) | 30.13 (11) | 73.37 (11) |
B(C3-C8)/C(C9-C14) | 72.30 (18) | 81.43 (13) | 76.07 (12) | 75.30 (9) | 89.19 (6) |
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The oxime group (C═N—OH) possesses stronger hydrogen-bonding capabilities than alcohols, phenols and carboxylic acids (Marsman et al., 1999). Intermolecular hydrogen bonding has received considerable attention among the range of directional non-covalent intermolecular interactions, which combine moderate strength and directionality, in designing compounds to form supramolecular structures (Karle et al., 1996). The crystal structure determination of the title compounds, N1-(4-tert-butylphenyl)-N2-hydroxy-α-oxo-α-phenylacetamidine, (I), and N1-(4-nitrophenyl)-N2-hydroxy-α-oxo-α-phenylacetamidine hemihydrate, (IIA) and (IIB) (two independent molecules), were carried out to determine the strength of the hydrogen-bonding capabilities of the oxime group, to establish the molecular arrangements, and also to compare the geometry of the oxime moiety with those found in the related compounds 2-[benzoyl(hydroxyimino)methylamino]benzoic acid, (III) (Soylu Taş Batı et al., 2004), and N1-(2,6-dimethylphenyl)-N2-hydroxy-α-oxo-α-phenylacetamidine, (IV) (Soylu Taş Saraco~glu et al., 2004). \sch
Compound (I) crystallizes in the triclinic space group P1 (Fig. 1), whereas compound (II) crystallizes in the monoclinic space group P21/n, with two independent molecules in the asymmetric unit (Fig. 3). Both compounds consist of two phenyl rings linked through an oxime moiety. The interplanar angles between the oxime moiety and the benzene rings are listed in Table 3.
While rings B (C3—C8) and C (C9—C14) are nearly perpendicular to each other in these and the above-mentioned related compounds, those in (IIA) and (IIB) are much more coplanar than those in (I). The oxime moiety in (I) and (IIA) and (IIB) has an E conformation, with appropriate C2—C1═N1—O1 torsion angles. There are no significant differences in the C1═N1 bond distances or in the C2—C1═N1 bond angles (Table 3). The bond lengths and angles of the oxime moiety in (I) are in close accord with the reported values for (III).
Analysis of the crystal packing of (I) and (II) shows significant differences. The molecules of (I) are linked by a nearly linear O—H···N hydrogen bond and a rather weak C—H···O hydrogen bond (Table 1). Atom O1 of the oxime group behaves as a donor, resulting in the formation of O1—H1O···N1 hydrogen bonds which link two molecules related by an inversion centre, an R22(6)-type dimeric arrangement; the intermolecular C10—H10···O2(x − 1, y, z) hydrogen bond is type C11(7) (Bernstein et al., 1995). This interaction links the dimers along the a axis and, as a consequence of this hydrogen bond, the molecules form interesting polymers approximately along the a axis in the crystal, as illustrated in Fig. 2.
In compound (II), the water O atom, O1W, is involved in four hydrogen bonds, two as a donor and two as an acceptor (Table 2 and Fig. 4). There are close contacts between the water and hydroxy groups (H1A—H1W and H1B—H2W). This may relate to the observed disorder of the water H atoms. The crystal packing is therefore stabilized by intermolecular hydrogen bonds, which form a polymeric arrangement parallel to the a axis. While compound (I) forms a polymeric arrangement of symmetry-related molecules, compound (II) arranges polymeric chains of molecules with solvate water molecules, suggesting the hydrogen-bonding interactions in (II) are stronger than in (I). Weak dipole-dipole and van der Waals interactions are also present in both compounds.