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The crystal structures of six anti-β-ketoarylhydrazones are reported: (a1) (E)-2-(4-cyanophenylhydrazono)-3-oxo­butanenitrile; (a2) (E)-2-(4-methylphenylhydraz­ono)-3-oxobutanenitrile; (a3) (E)-2-(4-acetylphenyl­hydrazono)-3-oxobutanenitrile; (a4) (E)-2-(2-methoxy-phenylhydrazono)-3-oxobutanenitrile; (a5) (E)-2-(2-acetylphenylhydrazono)-3-oxobutanenitrile; (a6) (E)-2-(2-nitrophenylhydrazono)-3-oxobutanenitrile. All com­pounds contain the π-conjugated heterodienic group HN—N=C—C=O and could form, at least in principle, chains of intermolecular N—H...O hydrogen bonds assisted by resonance (RAHB-inter). Compounds (a1) and (a2) form this kind of hydrogen bond though with rather long N...O distances of 2.948 (3) and 2.980 (2) Å, and compound (a6) undergoes the same interaction but even more weakened [N...O 3.150 (1) Å] by the intramolecular bifurcation of the hydrogen bond donated by the N—H group. The intrinsic weakness of the intermolecular RAHB makes possible the setting up of alternative packing arrangements that are controlled by an antiparallel dipole–dipole (DD) interaction between two C=O groups of the β-ketohydrazone moiety [compounds (a4) and (a5)]. The critical factors that cause the switching between the dif-ferent packings turn out to be the presence of hydrogen bonding accepting substituents on the phenyl and, most frequently, the intramolecular N—H...O bond with the O atom of the phenyl o-substituent. The crystal packing is widely determined by RAHB-inter (three cases) or DD (two cases) interactions. Only compound (a3) dis-plays a different packing arrangement, where the DD interaction is complemented by a non-resonant hydro-gen bond between a p-acetyl phenyl substituent and the hydrazone N—H group [N...O 2.907 (2) Å]. Crystal densities range from 1.24 to 1.44 Mg m−3 and are shown to increase with the number of intermolecular hydrogen bonds and other non-van der Waals interactions.

Supporting information

cif

Crystallographic Information File (CIF)
Contains datablocks global, a1, a2, a3, a4, a5, a6

hkl

Structure factor file (CIF format)
Contains datablock (a1)

hkl

Structure factor file (CIF format)
Contains datablock (a2)

hkl

Structure factor file (CIF format)
Contains datablock (a3)

hkl

Structure factor file (CIF format)
Contains datablock (a4)

hkl

Structure factor file (CIF format)
Contains datablock (a5)

hkl

Structure factor file (CIF format)
Contains datablock (a6)

CCDC references: 138560; 138561; 138562; 138563; 138564; 138565

Computing details top

For all compounds, data collection: CAD4, Enraf-Nonius, 1984; cell refinement: CAD4, Enraf-Nonius, 1984; data reduction: MolEN, C.K. Fair, Enraf-Nonius, 1990; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEPII, (Johnson, 1976) for a1; ORTEPII, Johnson, 1976 for a2; ORTEPII (Johnson, 1976) for a3, a4, a5, a6. Software used to prepare material for publication: PARST (Nardelli, 1983, 1995), SHELXL97 (Sheldrick, 1997) for a1, a2, a3; PARST (Nardelli, 1983; 1995),SHELXL97 (Sheldrick, 1997) for a4; PARST (Nardelli, 1983; 1995), SHELXL97 (Sheldrick, 1997) for a5; PARST (Nardelli, 1983;1995),SHELXL97 (Sheldrick, 1997) for a6.

(a1) E,2-(4-cyanophenylhydrazono)-3-oxobutanenitrile top
Crystal data top
C11H8N4OF(000) = 440
Mr = 212.21Dx = 1.287 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 7.196 (3) Åθ = 7–12°
b = 14.125 (2) ŵ = 0.09 mm1
c = 10.862 (2) ÅT = 293 K
β = 97.34 (3)°Needle, pale yellow
V = 1095.0 (5) Å30.43 × 0.12 × 0.10 mm
Z = 4
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.030
Radiation source: fine-focus sealed tubeθmax = 27.0°, θmin = 2.4°
Graphite monochromatorh = 09
ω/2θ scansk = 018
2556 measured reflectionsl = 1313
2366 independent reflections3 standard reflections every 120 min
1102 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063All H-atom parameters refined
wR(F2) = 0.169 w = 1/[σ2(Fo2) + (0.0852P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max = 0.029
2366 reflectionsΔρmax = 0.18 e Å3
178 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.002 (3)
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
xyzUiso*/Ueq
O10.0782 (3)0.24978 (15)0.34765 (19)0.0696 (7)
N10.1995 (3)0.10435 (16)0.0056 (2)0.0475 (6)
N20.1416 (3)0.10652 (14)0.11385 (18)0.0441 (6)
N30.0347 (5)0.3376 (2)0.0472 (3)0.1024 (12)
N40.5340 (4)0.2995 (2)0.2765 (3)0.0941 (11)
C10.0035 (4)0.1809 (2)0.3003 (3)0.0533 (7)
C20.0725 (4)0.18337 (18)0.1674 (2)0.0458 (7)
C30.0398 (7)0.0954 (3)0.3737 (4)0.0759 (11)
C40.0517 (4)0.2703 (2)0.1023 (3)0.0620 (9)
C50.2681 (3)0.02011 (17)0.0613 (2)0.0397 (6)
C60.3343 (4)0.0211 (2)0.1863 (3)0.0540 (8)
C70.4039 (4)0.0608 (2)0.2437 (3)0.0571 (8)
C80.4068 (4)0.14297 (19)0.1751 (3)0.0514 (7)
C90.3401 (4)0.1431 (2)0.0501 (3)0.0520 (7)
C100.2693 (4)0.06204 (18)0.0077 (3)0.0457 (7)
C110.4784 (4)0.2298 (2)0.2325 (3)0.0679 (9)
H10.201 (3)0.1529 (18)0.045 (2)0.038 (7)*
H310.037 (6)0.093 (3)0.446 (4)0.129 (16)*
H320.030 (5)0.038 (3)0.326 (4)0.108 (13)*
H330.167 (8)0.094 (4)0.389 (5)0.18 (2)*
H60.333 (3)0.0763 (18)0.238 (2)0.047 (7)*
H70.453 (4)0.0597 (17)0.326 (3)0.052 (8)*
H90.345 (4)0.1941 (19)0.014 (3)0.053 (9)*
H100.231 (4)0.0627 (19)0.097 (3)0.076 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0827 (15)0.0651 (13)0.0577 (13)0.0121 (12)0.0030 (10)0.0168 (11)
N10.0633 (16)0.0372 (14)0.0392 (13)0.0006 (11)0.0035 (10)0.0018 (11)
N20.0449 (13)0.0438 (12)0.0428 (13)0.0032 (10)0.0021 (9)0.0065 (10)
N30.171 (3)0.0585 (18)0.069 (2)0.021 (2)0.0155 (19)0.0086 (16)
N40.104 (2)0.082 (2)0.096 (2)0.0215 (18)0.0064 (18)0.0364 (18)
C10.0556 (18)0.0551 (18)0.0485 (18)0.0004 (14)0.0042 (13)0.0113 (14)
C20.0507 (17)0.0442 (15)0.0420 (15)0.0011 (13)0.0037 (12)0.0037 (12)
C30.106 (4)0.069 (2)0.050 (2)0.013 (2)0.000 (2)0.0050 (18)
C40.086 (2)0.0459 (17)0.0508 (18)0.0064 (16)0.0056 (15)0.0052 (14)
C50.0412 (15)0.0373 (13)0.0400 (14)0.0051 (11)0.0027 (11)0.0036 (11)
C60.067 (2)0.0461 (16)0.0452 (16)0.0052 (14)0.0062 (13)0.0006 (14)
C70.0599 (19)0.0632 (19)0.0441 (17)0.0023 (15)0.0089 (13)0.0099 (15)
C80.0447 (16)0.0538 (17)0.0553 (18)0.0021 (13)0.0049 (13)0.0146 (14)
C90.0585 (19)0.0414 (17)0.058 (2)0.0004 (14)0.0132 (14)0.0008 (14)
C100.0521 (17)0.0443 (15)0.0405 (15)0.0007 (12)0.0052 (12)0.0014 (13)
C110.061 (2)0.066 (2)0.077 (2)0.0056 (16)0.0062 (16)0.0225 (17)
Geometric parameters (Å, º) top
O1—C11.216 (3)C3—H330.95 (5)
N1—N21.311 (3)C5—C61.380 (3)
N1—C51.396 (3)C5—C101.382 (3)
N1—H10.81 (2)C6—C71.378 (4)
N2—C21.300 (3)C6—H60.96 (2)
N3—C41.139 (4)C7—C81.381 (4)
N4—C111.144 (4)C7—H70.92 (3)
C1—C21.465 (4)C8—C91.380 (4)
C1—C31.489 (5)C8—C111.441 (4)
C2—C41.434 (4)C9—C101.373 (4)
C3—H310.90 (4)C9—H90.82 (3)
C3—H320.96 (4)C10—H100.98 (3)
N2—N1—C5119.9 (2)C6—C5—N1118.4 (2)
N2—N1—H1118.8 (18)C10—C5—N1120.4 (2)
C5—N1—H1121.1 (18)C7—C6—C5119.8 (3)
C2—N2—N1121.1 (2)C7—C6—H6116.7 (15)
O1—C1—C2118.8 (3)C5—C6—H6123.5 (15)
O1—C1—C3122.1 (3)C6—C7—C8119.4 (3)
C2—C1—C3119.1 (3)C6—C7—H7119.8 (16)
N2—C2—C4123.5 (2)C8—C7—H7120.7 (16)
N2—C2—C1118.9 (2)C7—C8—C9120.3 (3)
C4—C2—C1117.5 (2)C7—C8—C11120.7 (3)
C1—C3—H31112 (3)C9—C8—C11119.0 (3)
C1—C3—H32111 (2)C10—C9—C8120.7 (3)
H31—C3—H32111 (4)C10—C9—H9123 (2)
C1—C3—H33111 (3)C8—C9—H9116 (2)
H31—C3—H33110 (4)C9—C10—C5118.7 (3)
H32—C3—H33102 (4)C9—C10—H10119.3 (17)
N3—C4—C2177.7 (3)C5—C10—H10121.9 (17)
C6—C5—C10121.1 (2)N4—C11—C8178.9 (4)
(a2) E,2-(4-methylphenylhydrazono)-3-oxobutanenitrile top
Crystal data top
C11H11N3OF(000) = 424
Mr = 201.23Dx = 1.238 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 7.052 (2) Åθ = 7–13°
b = 13.211 (2) ŵ = 0.08 mm1
c = 11.996 (2) ÅT = 293 K
β = 104.96 (2)°Prism, yellow
V = 1079.7 (4) Å30.52 × 0.21 × 0.20 mm
Z = 4
Data collection top
Enraf-Nonius CAD.4
diffractometer
Rint = 0.020
Radiation source: fine-focus sealed tubeθmax = 28.0°, θmin = 2.3°
Graphite monochromatorh = 09
ω/2θ scansk = 017
2804 measured reflectionsl = 1515
2595 independent reflections3 standard reflections every 120 min
1814 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: difference Fourier map
wR(F2) = 0.140All H-atom parameters refined
S = 1.06 w = 1/[σ2(Fo2) + (0.0786P)2 + 0.0758P]
where P = (Fo2 + 2Fc2)/3
2595 reflections(Δ/σ)max = 0.004
180 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.17 e Å3
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
xyzUiso*/Ueq
O10.55541 (18)0.24559 (8)0.33934 (9)0.0639 (3)
N10.26532 (16)0.09213 (8)0.00410 (9)0.0410 (3)
N20.34472 (15)0.08998 (8)0.10647 (9)0.0401 (3)
N30.4054 (3)0.34512 (12)0.06338 (14)0.0890 (6)
C10.4932 (2)0.16810 (10)0.28849 (12)0.0467 (3)
C20.40903 (19)0.17286 (10)0.16307 (11)0.0427 (3)
C30.4951 (3)0.06939 (15)0.34793 (16)0.0644 (5)
C40.4058 (2)0.26981 (12)0.10833 (13)0.0550 (4)
C50.20080 (17)0.00155 (9)0.06422 (10)0.0380 (3)
C60.1240 (2)0.00591 (11)0.18243 (12)0.0458 (3)
C70.0637 (2)0.08170 (12)0.24403 (13)0.0508 (4)
C80.0768 (2)0.17477 (11)0.18892 (14)0.0492 (4)
C90.1516 (2)0.17712 (11)0.07061 (14)0.0522 (4)
C100.2144 (2)0.09033 (10)0.00734 (12)0.0460 (3)
C110.0101 (3)0.27041 (15)0.2564 (2)0.0730 (5)
H10.241 (2)0.1493 (14)0.0427 (15)0.053 (4)*
H310.556 (4)0.0762 (19)0.422 (3)0.115 (8)*
H320.537 (4)0.016 (2)0.312 (3)0.126 (10)*
H330.374 (5)0.038 (2)0.343 (3)0.150 (12)*
H60.109 (3)0.0698 (15)0.2203 (17)0.071 (5)*
H70.018 (2)0.0754 (12)0.3304 (15)0.060 (5)*
H90.160 (3)0.2426 (15)0.0319 (16)0.072 (5)*
H100.258 (2)0.0921 (12)0.0721 (15)0.051 (4)*
H1110.096 (4)0.301 (2)0.237 (2)0.123 (10)*
H1120.019 (5)0.262 (3)0.343 (3)0.159 (12)*
H1130.120 (6)0.316 (3)0.246 (3)0.162 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0801 (8)0.0540 (6)0.0472 (6)0.0052 (5)0.0024 (5)0.0146 (5)
N10.0467 (6)0.0350 (6)0.0367 (6)0.0011 (4)0.0022 (4)0.0004 (4)
N20.0386 (5)0.0409 (6)0.0378 (5)0.0008 (4)0.0043 (4)0.0041 (4)
N30.1216 (15)0.0551 (9)0.0683 (10)0.0136 (9)0.0154 (9)0.0099 (7)
C10.0482 (7)0.0468 (7)0.0412 (7)0.0010 (6)0.0048 (6)0.0071 (6)
C20.0446 (7)0.0396 (7)0.0401 (7)0.0012 (5)0.0039 (5)0.0039 (5)
C30.0811 (12)0.0594 (10)0.0456 (9)0.0099 (9)0.0037 (8)0.0034 (7)
C40.0638 (9)0.0433 (8)0.0469 (8)0.0059 (6)0.0055 (6)0.0062 (6)
C50.0382 (6)0.0359 (6)0.0378 (6)0.0001 (5)0.0062 (5)0.0035 (5)
C60.0514 (8)0.0422 (7)0.0390 (7)0.0013 (6)0.0030 (5)0.0007 (5)
C70.0516 (8)0.0556 (9)0.0409 (7)0.0024 (6)0.0039 (6)0.0097 (6)
C80.0425 (7)0.0456 (7)0.0586 (8)0.0032 (6)0.0116 (6)0.0155 (6)
C90.0595 (9)0.0348 (7)0.0617 (9)0.0018 (6)0.0144 (7)0.0002 (6)
C100.0556 (8)0.0400 (7)0.0395 (7)0.0029 (6)0.0070 (6)0.0012 (5)
C110.0734 (12)0.0553 (10)0.0899 (14)0.0145 (9)0.0206 (11)0.0350 (10)
Geometric parameters (Å, º) top
O1—C11.2142 (17)C5—C101.3836 (18)
N1—N21.3001 (15)C6—C71.3800 (19)
N1—C51.4105 (16)C6—H60.951 (19)
N1—H10.880 (19)C7—C81.388 (2)
N2—C21.3063 (16)C7—H71.006 (17)
N3—C41.131 (2)C8—C91.381 (2)
C1—C21.4693 (18)C8—C111.509 (2)
C1—C31.485 (2)C9—C101.3832 (19)
C2—C41.437 (2)C9—H90.976 (19)
C3—H310.89 (3)C10—H100.923 (16)
C3—H320.92 (3)C11—H1110.93 (3)
C3—H330.93 (3)C11—H1121.01 (4)
C5—C61.3823 (18)C11—H1130.96 (4)
N2—N1—C5120.02 (11)C7—C6—H6120.4 (12)
N2—N1—H1122.0 (11)C5—C6—H6119.6 (12)
C5—N1—H1117.8 (11)C6—C7—C8120.97 (13)
N1—N2—C2120.82 (11)C6—C7—H7117.0 (10)
O1—C1—C2118.46 (13)C8—C7—H7121.9 (10)
O1—C1—C3122.82 (13)C9—C8—C7118.05 (12)
C2—C1—C3118.71 (12)C9—C8—C11121.07 (15)
N2—C2—C4123.17 (12)C7—C8—C11120.87 (16)
N2—C2—C1119.39 (12)C8—C9—C10121.91 (13)
C4—C2—C1117.42 (11)C8—C9—H9118.0 (11)
C1—C3—H31109.7 (17)C10—C9—H9120.1 (11)
C1—C3—H32114.5 (18)C9—C10—C5119.01 (13)
H31—C3—H32115 (2)C9—C10—H10121.3 (10)
C1—C3—H33117.5 (19)C5—C10—H10119.5 (10)
H31—C3—H33108 (2)C8—C11—H111113.1 (17)
H32—C3—H3392 (2)C8—C11—H112114 (2)
N3—C4—C2178.37 (19)H111—C11—H112110 (3)
C6—C5—C10120.09 (12)C8—C11—H113109 (2)
C6—C5—N1118.58 (11)H111—C11—H113111 (3)
C10—C5—N1121.33 (11)H112—C11—H11398 (3)
C7—C6—C5119.96 (13)
(a3) E,2-(4-acetylphenylhydrazono)-3-oxobutanenitrile top
Crystal data top
C12H11N3O2F(000) = 480
Mr = 229.24Dx = 1.336 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 8.638 (3) Åθ = 8–12°
b = 10.841 (2) ŵ = 0.09 mm1
c = 12.208 (2) ÅT = 293 K
β = 94.69 (2)°Prism, yellow
V = 1139.4 (5) Å30.28 × 0.19 × 0.14 mm
Z = 4
Data collection top
Enraf-Nonius CAD4
diffractometer
Rint = 0.012
Radiation source: fine-focus sealed tubeθmax = 28.0°, θmin = 2.5°
Graphite monochromatorh = 011
ω/2θ scansk = 014
2921 measured reflectionsl = 1616
2741 independent reflections3 standard reflections every 120 min
1735 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: difference Fourier map
wR(F2) = 0.155All H-atom parameters refined
S = 1.05 w = 1/[σ2(Fo2) + (0.0888P)2]
where P = (Fo2 + 2Fc2)/3
2741 reflections(Δ/σ)max = 0.013
198 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.20 e Å3
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
xyzUiso*/Ueq
O10.15747 (17)0.04192 (14)0.43980 (12)0.0601 (4)
O20.50189 (17)0.83438 (13)0.65804 (11)0.0556 (4)
N10.07426 (18)0.36408 (14)0.60706 (13)0.0407 (4)
N20.05251 (16)0.29449 (13)0.52129 (12)0.0386 (4)
N30.1989 (2)0.14192 (19)0.71043 (17)0.0700 (6)
C10.0631 (2)0.12560 (17)0.43237 (15)0.0436 (4)
C20.0419 (2)0.20171 (16)0.52987 (14)0.0399 (4)
C30.0324 (4)0.1540 (3)0.3294 (2)0.0621 (6)
C40.1307 (2)0.16739 (18)0.63113 (16)0.0465 (5)
C50.17546 (19)0.46556 (15)0.59488 (14)0.0358 (4)
C60.2475 (2)0.49876 (17)0.49332 (14)0.0402 (4)
C70.3452 (2)0.59993 (17)0.48727 (14)0.0402 (4)
C80.37382 (19)0.66866 (15)0.57949 (13)0.0358 (4)
C90.2998 (2)0.63279 (18)0.67998 (15)0.0464 (5)
C100.2017 (2)0.53268 (18)0.68853 (15)0.0479 (5)
C110.4779 (2)0.77824 (16)0.57467 (14)0.0394 (4)
C120.5520 (3)0.8214 (2)0.46668 (18)0.0533 (5)
H10.027 (2)0.3500 (18)0.6757 (18)0.045 (5)*
H310.034 (3)0.236 (3)0.312 (2)0.096 (10)*
H320.003 (3)0.113 (3)0.276 (3)0.095 (10)*
H330.137 (4)0.129 (3)0.339 (3)0.094 (10)*
H60.237 (2)0.449 (2)0.4332 (18)0.054 (6)*
H70.396 (2)0.6161 (17)0.4197 (16)0.037 (5)*
H90.316 (2)0.678 (2)0.7466 (18)0.054 (6)*
H100.146 (2)0.511 (2)0.7592 (18)0.054 (6)*
H1210.623 (3)0.888 (3)0.483 (2)0.089 (9)*
H1220.602 (4)0.751 (4)0.429 (3)0.121 (12)*
H1230.472 (4)0.853 (3)0.421 (3)0.095 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0648 (9)0.0540 (9)0.0628 (9)0.0206 (7)0.0127 (7)0.0020 (7)
O20.0718 (9)0.0512 (8)0.0440 (7)0.0127 (7)0.0056 (6)0.0082 (6)
N10.0476 (9)0.0387 (8)0.0359 (8)0.0038 (6)0.0033 (6)0.0003 (6)
N20.0419 (8)0.0337 (7)0.0411 (8)0.0007 (6)0.0084 (6)0.0002 (6)
N30.0756 (13)0.0719 (13)0.0596 (11)0.0039 (11)0.0127 (10)0.0021 (10)
C10.0490 (10)0.0387 (9)0.0442 (10)0.0025 (8)0.0097 (8)0.0010 (8)
C20.0407 (9)0.0366 (9)0.0426 (9)0.0004 (7)0.0039 (7)0.0038 (7)
C30.0875 (19)0.0529 (14)0.0448 (12)0.0121 (13)0.0012 (11)0.0029 (10)
C40.0446 (10)0.0437 (10)0.0509 (11)0.0013 (8)0.0026 (8)0.0003 (8)
C50.0388 (9)0.0311 (8)0.0380 (8)0.0011 (7)0.0062 (7)0.0004 (7)
C60.0487 (10)0.0389 (9)0.0332 (9)0.0006 (8)0.0045 (7)0.0031 (8)
C70.0454 (10)0.0426 (10)0.0320 (9)0.0001 (8)0.0005 (7)0.0004 (7)
C80.0378 (8)0.0347 (8)0.0349 (8)0.0027 (7)0.0031 (6)0.0009 (7)
C90.0586 (12)0.0455 (10)0.0351 (9)0.0092 (9)0.0044 (8)0.0039 (8)
C100.0617 (12)0.0503 (11)0.0313 (9)0.0095 (9)0.0004 (8)0.0005 (8)
C110.0416 (9)0.0364 (9)0.0406 (9)0.0033 (7)0.0051 (7)0.0030 (7)
C120.0567 (12)0.0539 (12)0.0483 (11)0.0151 (11)0.0023 (9)0.0028 (10)
Geometric parameters (Å, º) top
O1—C11.218 (2)C5—C101.389 (2)
O2—C111.218 (2)C6—C71.382 (3)
N1—N21.316 (2)C6—H60.92 (2)
N1—C51.406 (2)C7—C81.389 (2)
N1—H10.92 (2)C7—H70.918 (19)
N2—C21.294 (2)C8—C91.392 (2)
N3—C41.126 (3)C8—C111.488 (2)
C1—C21.472 (3)C9—C101.376 (3)
C1—C31.479 (3)C9—H90.97 (2)
C2—C41.449 (3)C10—H100.98 (2)
C3—H310.91 (3)C11—C121.493 (3)
C3—H320.86 (3)C12—H1210.97 (3)
C3—H330.96 (3)C12—H1220.97 (4)
C5—C61.388 (2)C12—H1230.98 (3)
N2—N1—C5119.50 (15)C5—C6—H6119.5 (13)
N2—N1—H1123.4 (12)C6—C7—C8122.06 (17)
C5—N1—H1117.1 (12)C6—C7—H7116.3 (11)
C2—N2—N1120.74 (15)C8—C7—H7121.5 (11)
O1—C1—C2118.97 (17)C7—C8—C9117.73 (16)
O1—C1—C3122.81 (19)C7—C8—C11122.90 (16)
C2—C1—C3118.22 (18)C9—C8—C11119.37 (15)
N2—C2—C4123.70 (17)C10—C9—C8121.54 (17)
N2—C2—C1119.33 (16)C10—C9—H9117.8 (12)
C4—C2—C1116.97 (16)C8—C9—H9120.7 (12)
C1—C3—H31113.1 (18)C9—C10—C5119.46 (17)
C1—C3—H32109 (2)C9—C10—H10120.5 (13)
H31—C3—H32109 (3)C5—C10—H10120.0 (13)
C1—C3—H33107.6 (19)O2—C11—C8120.63 (16)
H31—C3—H33108 (3)O2—C11—C12119.43 (17)
H32—C3—H33110 (3)C8—C11—C12119.93 (16)
N3—C4—C2179.2 (2)C11—C12—H121106.5 (17)
C6—C5—C10120.51 (16)C11—C12—H122108 (2)
C6—C5—N1121.79 (15)H121—C12—H122114 (3)
C10—C5—N1117.70 (16)C11—C12—H123109.8 (18)
C7—C6—C5118.72 (16)H121—C12—H123110 (2)
C7—C6—H6121.5 (13)H122—C12—H123108 (3)
(a4) E,2-(2-methylphenylhydrazono)-3-oxobutanenitrile top
Crystal data top
C11H11N3O2F(000) = 456
Mr = 217.23Dx = 1.258 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 25 reflections
a = 15.236 (2) Åθ = 9–14°
b = 6.618 (1) ŵ = 0.09 mm1
c = 11.379 (1) ÅT = 293 K
V = 1147.4 (3) Å3Prism, yellow
Z = 40.52 × 0.33 × 0.26 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
θmax = 28.0°, θmin = 2.2°
Radiation source: fine-focus sealed tubeh = 020
Graphite monochromatork = 08
1488 measured reflectionsl = 014
1488 independent reflections3 standard reflections every 120 min
881 reflections with I > 2σ(I) intensity decay: none
Rint = 0.000
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: difference Fourier map
wR(F2) = 0.146All H-atom parameters refined
S = 1.03 w = 1/[σ2(Fo2) + (0.0846P)2 + 0.008P]
where P = (Fo2 + 2Fc2)/3
1488 reflections(Δ/σ)max = 0.033
126 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.28 e Å3
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
xyzUiso*/Ueq
O10.02844 (17)0.25000.52530 (14)0.1259 (9)
O20.10460 (9)0.25000.07118 (13)0.0741 (5)
N10.01796 (10)0.25000.12454 (12)0.0520 (4)
N20.02023 (11)0.25000.22601 (12)0.0562 (4)
N30.19437 (18)0.25000.3077 (3)0.1285 (11)
C10.0167 (2)0.25000.43685 (17)0.0918 (9)
C20.02668 (15)0.25000.32217 (16)0.0679 (6)
C30.1145 (3)0.25000.4402 (3)0.1226 (13)
C40.1208 (2)0.25000.3184 (2)0.0844 (7)
C50.03075 (11)0.25000.02026 (14)0.0467 (4)
C60.01596 (12)0.25000.08446 (15)0.0524 (5)
C70.02834 (17)0.25000.19033 (16)0.0684 (6)
C80.11815 (18)0.25000.1906 (2)0.0828 (7)
C90.16428 (15)0.25000.0879 (2)0.0846 (7)
C100.12069 (13)0.25000.01847 (19)0.0637 (6)
C110.1568 (2)0.25000.1752 (3)0.1109 (11)
H10.0738 (14)0.25000.126 (2)0.066 (6)*
H70.0030 (16)0.25000.259 (3)0.097 (8)*
H80.1486 (18)0.25000.268 (3)0.109 (8)*
H90.2260 (17)0.25000.086 (2)0.098 (8)*
H100.1503 (14)0.25000.087 (2)0.078 (6)*
H1110.209 (3)0.25000.134 (4)0.155 (16)*
H1120.1502 (16)0.373 (5)0.223 (3)0.166 (11)*
H320.137 (2)0.369 (6)0.421 (4)0.25 (2)*
H310.134 (3)0.25000.509 (5)0.197 (19)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.209 (3)0.1296 (17)0.0391 (9)0.0000.0195 (11)0.000
O20.0643 (9)0.0989 (11)0.0591 (8)0.0000.0149 (7)0.000
N10.0537 (9)0.0672 (10)0.0350 (7)0.0000.0024 (6)0.000
N20.0737 (10)0.0602 (9)0.0347 (8)0.0000.0010 (6)0.000
N30.0952 (17)0.169 (3)0.122 (2)0.0000.0555 (15)0.000
C10.157 (3)0.0848 (17)0.0336 (10)0.0000.0043 (14)0.000
C20.0953 (15)0.0702 (13)0.0382 (10)0.0000.0127 (10)0.000
C30.147 (3)0.157 (4)0.0637 (17)0.0000.0389 (19)0.000
C40.1013 (19)0.0942 (18)0.0576 (13)0.0000.0382 (13)0.000
C50.0554 (10)0.0510 (10)0.0337 (8)0.0000.0038 (7)0.000
C60.0629 (10)0.0533 (11)0.0409 (9)0.0000.0037 (8)0.000
C70.1068 (18)0.0667 (13)0.0316 (9)0.0000.0036 (11)0.000
C80.0987 (18)0.1020 (18)0.0476 (12)0.0000.0288 (12)0.000
C90.0670 (13)0.111 (2)0.0752 (14)0.0000.0240 (12)0.000
C100.0555 (11)0.0851 (15)0.0504 (11)0.0000.0003 (9)0.000
C110.093 (2)0.154 (3)0.086 (2)0.0000.0430 (19)0.000
Geometric parameters (Å, º) top
O1—C11.219 (3)C5—C101.370 (3)
O2—C61.359 (2)C5—C61.388 (2)
O2—C111.426 (3)C6—C71.381 (3)
N1—N21.2930 (19)C7—C81.368 (4)
N1—C51.400 (2)C7—H70.91 (3)
N1—H10.85 (2)C8—C91.364 (4)
N2—C21.307 (2)C8—H81.00 (3)
N3—C41.128 (4)C9—C101.380 (3)
C1—C21.463 (3)C9—H90.94 (2)
C1—C31.491 (6)C10—H100.90 (2)
C2—C41.434 (4)C11—H1110.93 (4)
C3—H320.89 (4)C11—H1120.99 (3)
C3—H310.83 (6)
C6—O2—C11117.5 (2)O2—C6—C7125.65 (18)
N2—N1—C5121.23 (15)O2—C6—C5114.46 (15)
N2—N1—H1116.0 (15)C7—C6—C5119.89 (19)
C5—N1—H1122.8 (15)C8—C7—C6119.4 (2)
N1—N2—C2120.10 (19)C8—C7—H7121.4 (17)
O1—C1—C2118.8 (3)C6—C7—H7119.2 (17)
O1—C1—C3122.9 (3)C9—C8—C7120.9 (2)
C2—C1—C3118.3 (2)C9—C8—H8121.3 (16)
N2—C2—C4121.45 (19)C7—C8—H8117.8 (17)
N2—C2—C1120.0 (2)C8—C9—C10120.2 (2)
C4—C2—C1118.5 (2)C8—C9—H9122.0 (16)
C1—C3—H32112 (2)C10—C9—H9117.7 (16)
C1—C3—H31112 (3)C5—C10—C9119.6 (2)
H32—C3—H3195 (3)C5—C10—H10119.2 (14)
N3—C4—C2175.5 (3)C9—C10—H10121.2 (14)
C10—C5—C6120.00 (17)O2—C11—H11193 (3)
C10—C5—N1122.87 (16)O2—C11—H112113.8 (17)
C6—C5—N1117.13 (15)H111—C11—H112112 (2)
(a5) E,2-(2-acetylphenylhydrazono)-3-oxobutanenitrile top
Crystal data top
C12H11N3O2Z = 2
Mr = 229.24F(000) = 240
Triclinic, P1Dx = 1.275 Mg m3
Dm = 0 Mg m3
Dm measured by not measured
a = 6.878 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.241 (1) ÅCell parameters from 25 reflections
c = 11.395 (1) Åθ = 8–13°
α = 105.21 (1)°µ = 0.09 mm1
β = 96.62 (2)°T = 293 K
γ = 102.92 (2)°Prism, yellow
V = 597.0 (2) Å30.62 × 0.26 × 0.12 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.012
Radiation source: fine-focus sealed tubeθmax = 28.0°, θmin = 2.7°
Graphite monochromatorh = 09
ω/2θ scansk = 1010
3007 measured reflectionsl = 1514
2860 independent reflections3 standard reflections every 120 min
1963 reflections with I > 2σ(I)
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: difference Fourier map
wR(F2) = 0.150All H-atom parameters refined
S = 1.07 w = 1/[σ2(Fo2) + (0.0876P)2 + 0.0213P]
where P = (Fo2 + 2Fc2)/3
2860 reflections(Δ/σ)max = 0.005
198 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.20 e Å3
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
xyzUiso*/Ueq
O10.2577 (3)0.0215 (2)0.53703 (11)0.0987 (5)
O20.23578 (17)0.29952 (13)0.04881 (10)0.0580 (3)
N10.24747 (16)0.02907 (14)0.13378 (10)0.0421 (3)
N20.25454 (17)0.05167 (15)0.25018 (10)0.0465 (3)
N30.2365 (3)0.3601 (2)0.27239 (17)0.0935 (6)
C10.2617 (3)0.0588 (3)0.46217 (15)0.0695 (5)
C20.2517 (2)0.0332 (2)0.33163 (13)0.0521 (3)
C30.2763 (6)0.2483 (4)0.4977 (2)0.1011 (8)
C40.2417 (3)0.2159 (2)0.30019 (14)0.0613 (4)
C50.25261 (17)0.06358 (16)0.04689 (11)0.0388 (3)
C60.25152 (17)0.02450 (16)0.07770 (11)0.0405 (3)
C70.2615 (2)0.0742 (2)0.16154 (14)0.0514 (4)
C80.2683 (2)0.2480 (2)0.12429 (16)0.0605 (4)
C90.2645 (2)0.3294 (2)0.00314 (16)0.0577 (4)
C100.2573 (2)0.23906 (18)0.08260 (15)0.0487 (3)
C110.2386 (2)0.21298 (18)0.12026 (12)0.0457 (3)
C120.2270 (4)0.3009 (3)0.25512 (17)0.0714 (5)
H10.238 (2)0.147 (2)0.1044 (15)0.054 (4)*
H310.346 (5)0.303 (4)0.574 (3)0.152 (11)*
H320.153 (7)0.267 (5)0.469 (4)0.197 (17)*
H330.328 (6)0.304 (5)0.448 (4)0.173 (15)*
H70.258 (3)0.017 (2)0.2454 (19)0.062 (5)*
H80.276 (3)0.311 (3)0.1830 (19)0.083 (6)*
H90.267 (3)0.440 (3)0.0181 (19)0.077 (5)*
H100.255 (3)0.297 (2)0.1640 (19)0.066 (5)*
H1210.209 (4)0.418 (4)0.266 (3)0.128 (10)*
H1220.352 (5)0.252 (3)0.287 (3)0.131 (9)*
H1230.121 (5)0.297 (4)0.302 (3)0.134 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1422 (14)0.1223 (12)0.0429 (7)0.0386 (10)0.0243 (7)0.0375 (8)
O20.0786 (7)0.0496 (6)0.0565 (6)0.0267 (5)0.0179 (5)0.0233 (5)
N10.0522 (6)0.0446 (6)0.0369 (6)0.0171 (5)0.0126 (4)0.0191 (4)
N20.0499 (6)0.0544 (6)0.0390 (6)0.0159 (5)0.0095 (4)0.0178 (5)
N30.1372 (17)0.0686 (10)0.0806 (12)0.0276 (10)0.0196 (11)0.0320 (9)
C10.0836 (12)0.0891 (12)0.0404 (8)0.0272 (9)0.0132 (7)0.0223 (8)
C20.0595 (8)0.0617 (8)0.0401 (7)0.0176 (6)0.0102 (6)0.0219 (6)
C30.161 (3)0.0886 (16)0.0496 (11)0.0465 (16)0.0117 (14)0.0057 (11)
C40.0780 (11)0.0668 (10)0.0463 (8)0.0174 (8)0.0113 (7)0.0304 (7)
C50.0376 (6)0.0456 (6)0.0409 (6)0.0143 (5)0.0104 (5)0.0219 (5)
C60.0386 (6)0.0496 (7)0.0410 (6)0.0152 (5)0.0105 (5)0.0221 (5)
C70.0544 (8)0.0664 (9)0.0440 (8)0.0195 (6)0.0135 (6)0.0296 (7)
C80.0686 (9)0.0658 (9)0.0659 (9)0.0220 (7)0.0167 (7)0.0461 (8)
C90.0652 (9)0.0476 (8)0.0723 (10)0.0216 (7)0.0182 (7)0.0300 (7)
C100.0522 (8)0.0480 (7)0.0534 (8)0.0184 (6)0.0151 (6)0.0211 (6)
C110.0446 (7)0.0506 (7)0.0464 (7)0.0160 (5)0.0116 (5)0.0181 (6)
C120.0976 (15)0.0627 (11)0.0476 (9)0.0160 (10)0.0161 (9)0.0089 (7)
Geometric parameters (Å, º) top
O1—C11.208 (2)C5—C61.4132 (18)
O2—C111.2141 (15)C6—C71.4058 (17)
N1—N21.3085 (16)C6—C111.4795 (18)
N1—C51.3990 (15)C7—C81.372 (2)
N1—H10.924 (16)C7—H70.94 (2)
N2—C21.3001 (17)C8—C91.373 (2)
N3—C41.137 (2)C8—H80.95 (2)
C1—C21.468 (2)C9—C101.374 (2)
C1—C31.484 (3)C9—H90.87 (2)
C2—C41.437 (2)C10—H100.93 (2)
C3—H310.89 (4)C11—C121.501 (2)
C3—H320.93 (4)C12—H1210.92 (3)
C3—H330.87 (4)C12—H1221.01 (3)
C5—C101.3875 (18)C12—H1230.86 (3)
N2—N1—C5119.81 (11)C5—C6—C11122.19 (11)
N2—N1—H1123.4 (10)C8—C7—C6121.33 (14)
C5—N1—H1116.8 (10)C8—C7—H7120.4 (10)
C2—N2—N1120.15 (12)C6—C7—H7118.3 (10)
O1—C1—C2119.22 (17)C7—C8—C9120.18 (13)
O1—C1—C3122.18 (17)C7—C8—H8119.4 (12)
C2—C1—C3118.60 (16)C9—C8—H8120.5 (12)
N2—C2—C4122.81 (13)C8—C9—C10120.67 (14)
N2—C2—C1119.74 (14)C8—C9—H9118.5 (13)
C4—C2—C1117.44 (13)C10—C9—H9120.8 (13)
C1—C3—H31112 (2)C9—C10—C5119.95 (14)
C1—C3—H32110 (3)C9—C10—H10119.3 (11)
H31—C3—H32123 (3)C5—C10—H10120.8 (11)
C1—C3—H33115 (3)O2—C11—C6121.63 (12)
H31—C3—H33108 (3)O2—C11—C12118.79 (14)
H32—C3—H3387 (3)C6—C11—C12119.58 (13)
N3—C4—C2177.98 (18)C11—C12—H121107.8 (18)
C10—C5—N1120.38 (12)C11—C12—H122112.6 (16)
C10—C5—C6120.60 (12)H121—C12—H122111 (2)
N1—C5—C6119.02 (11)C11—C12—H123113 (2)
C7—C6—C5117.24 (12)H121—C12—H123103 (2)
C7—C6—C11120.57 (12)H122—C12—H123109 (2)
(a6) E, 2-(2-nitrophenylhydrazono)-3-oxobutanenitrile top
Crystal data top
C10H8N4O3F(000) = 480
Mr = 232.20Dx = 1.443 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 7.184 (1) Åθ = 9–13°
b = 19.491 (2) ŵ = 0.11 mm1
c = 8.084 (1) ÅT = 293 K
β = 109.27 (1)°Prism, orange
V = 1068.5 (2) Å30.60 × 0.26 × 0.21 mm
Z = 4
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.025
Radiation source: fine-focus sealed tubeθmax = 28.0°, θmin = 2.1°
Graphite monochromatorh = 09
ω/2θ scansk = 025
2750 measured reflectionsl = 1010
2580 independent reflections3 standard reflections every 120 min
1996 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: difference Fourier map
wR(F2) = 0.117All H-atom parameters refined
S = 1.09 w = 1/[σ2(Fo2) + (0.0591P)2 + 0.1463P]
where P = (Fo2 + 2Fc2)/3
2580 reflections(Δ/σ)max = 0.002
186 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.20 e Å3
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
xyzUiso*/Ueq
O10.01208 (19)0.29010 (5)0.29443 (15)0.0624 (3)
O30.2797 (2)0.02195 (6)0.48349 (14)0.0682 (4)
O20.2401 (2)0.07871 (6)0.37349 (14)0.0736 (4)
N10.17042 (16)0.09605 (5)0.03822 (14)0.0363 (2)
N20.12301 (15)0.12882 (5)0.11270 (13)0.0353 (2)
N30.0215 (3)0.25581 (7)0.1420 (2)0.0710 (4)
N40.26505 (18)0.01702 (6)0.36236 (14)0.0451 (3)
C10.0209 (2)0.22906 (7)0.29076 (18)0.0439 (3)
C20.06635 (19)0.19232 (6)0.12169 (16)0.0376 (3)
C30.0150 (4)0.18849 (10)0.4473 (2)0.0637 (5)
C40.0427 (2)0.22907 (7)0.02465 (19)0.0449 (3)
C50.23043 (17)0.02783 (6)0.04526 (15)0.0320 (2)
C60.28031 (18)0.01077 (6)0.20023 (15)0.0347 (3)
C70.3447 (2)0.07831 (7)0.20570 (18)0.0405 (3)
C80.3568 (2)0.10876 (7)0.05646 (19)0.0445 (3)
C90.3024 (2)0.07186 (7)0.09862 (18)0.0423 (3)
C100.24042 (19)0.00492 (6)0.10542 (16)0.0365 (3)
H10.182 (2)0.1171 (8)0.135 (2)0.047 (4)*
H310.026 (4)0.2161 (14)0.546 (3)0.106 (8)*
H320.064 (4)0.1475 (15)0.460 (3)0.108 (8)*
H330.134 (5)0.1682 (15)0.434 (3)0.121 (10)*
H70.378 (2)0.1019 (8)0.313 (2)0.054 (4)*
H80.402 (2)0.1554 (8)0.059 (2)0.047 (4)*
H90.305 (2)0.0934 (8)0.201 (2)0.054 (4)*
H100.204 (2)0.0200 (8)0.209 (2)0.044 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0807 (8)0.0374 (6)0.0700 (7)0.0076 (5)0.0260 (6)0.0155 (5)
O30.0986 (10)0.0708 (8)0.0422 (6)0.0060 (7)0.0329 (6)0.0121 (5)
O20.1245 (12)0.0544 (7)0.0429 (6)0.0252 (7)0.0292 (7)0.0041 (5)
N10.0465 (6)0.0299 (5)0.0329 (5)0.0027 (4)0.0134 (4)0.0008 (4)
N20.0371 (5)0.0309 (5)0.0382 (5)0.0004 (4)0.0125 (4)0.0027 (4)
N30.0995 (12)0.0542 (8)0.0650 (9)0.0077 (8)0.0349 (8)0.0097 (7)
N40.0529 (7)0.0487 (7)0.0338 (5)0.0052 (5)0.0143 (5)0.0007 (5)
C10.0451 (7)0.0378 (7)0.0498 (8)0.0013 (5)0.0169 (6)0.0101 (5)
C20.0401 (6)0.0312 (6)0.0419 (6)0.0006 (5)0.0142 (5)0.0008 (5)
C30.0920 (14)0.0570 (10)0.0468 (8)0.0085 (10)0.0292 (9)0.0095 (8)
C40.0534 (8)0.0318 (6)0.0495 (8)0.0033 (6)0.0168 (6)0.0003 (5)
C50.0323 (6)0.0292 (5)0.0348 (6)0.0009 (4)0.0115 (5)0.0002 (4)
C60.0364 (6)0.0353 (6)0.0330 (6)0.0006 (5)0.0121 (5)0.0002 (5)
C70.0431 (7)0.0351 (6)0.0434 (7)0.0018 (5)0.0146 (5)0.0079 (5)
C80.0493 (8)0.0298 (6)0.0571 (8)0.0037 (5)0.0211 (6)0.0001 (5)
C90.0488 (7)0.0368 (6)0.0444 (7)0.0008 (5)0.0197 (6)0.0081 (5)
C100.0414 (6)0.0352 (6)0.0343 (6)0.0006 (5)0.0143 (5)0.0007 (5)
Geometric parameters (Å, º) top
O1—C11.2115 (17)C3—H320.96 (3)
O3—N41.2161 (15)C3—H330.91 (3)
O2—N41.2233 (16)C5—C101.3979 (16)
N1—N21.3184 (14)C5—C61.4027 (16)
N1—C51.3931 (15)C6—C71.3912 (17)
N1—H10.864 (17)C7—C81.3727 (19)
N2—C21.2974 (15)C7—H70.943 (17)
N3—C41.1360 (19)C8—C91.385 (2)
N4—C61.4554 (16)C8—H80.963 (16)
C1—C21.4808 (18)C9—C101.3738 (18)
C1—C31.481 (2)C9—H90.936 (17)
C2—C41.4403 (18)C10—H100.928 (16)
C3—H310.93 (3)
N2—N1—C5118.83 (10)N3—C4—C2177.40 (16)
N2—N1—H1121.8 (11)N1—C5—C10120.29 (11)
C5—N1—H1118.8 (11)N1—C5—C6122.19 (11)
C2—N2—N1119.64 (10)C10—C5—C6117.51 (11)
O3—N4—O2122.04 (12)C7—C6—C5121.34 (11)
O3—N4—C6118.72 (12)C7—C6—N4116.53 (11)
O2—N4—C6119.24 (11)C5—C6—N4122.12 (11)
O1—C1—C2118.64 (13)C8—C7—C6119.87 (12)
O1—C1—C3123.58 (14)C8—C7—H7122.0 (10)
C2—C1—C3117.78 (13)C6—C7—H7118.2 (10)
N2—C2—C4123.25 (11)C7—C8—C9119.35 (12)
N2—C2—C1118.86 (11)C7—C8—H8120.4 (9)
C4—C2—C1117.89 (11)C9—C8—H8120.3 (9)
C1—C3—H31109.7 (16)C10—C9—C8121.36 (12)
C1—C3—H32112.7 (15)C10—C9—H9119.4 (10)
H31—C3—H32112 (2)C8—C9—H9119.2 (10)
C1—C3—H33111.8 (17)C9—C10—C5120.53 (12)
H31—C3—H33112 (2)C9—C10—H10121.7 (9)
H32—C3—H3398 (2)C5—C10—H10117.8 (9)
 
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