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In the title compound, C21H32N4O4, no disorder is present in the 15-membered hydro­carbon ring, which exists in an unsymmetrical quinquangular [12345] conformation. The 2,4-dinitro­phenyl­hydrazone group is approximately perpendicular to the C15 ring, with a dihedral angle of 84.66 (1)° between their best planes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270108002898/av3135sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108002898/av3135Isup2.hkl
Contains datablock I

CCDC reference: 682821

Comment top

Semiquantitative calculations for cyclopentadecane, (II), indicated that the first five lowest-energy conformations considered were all quinquangular and that the [33333] conformation was the most stable (Dale, 1973). Five triangular conformations were found among the next nine conformations in order of energy, but quadrangular conformations were absent (Dale, 1973).

MOLBUILD (Boyd, 1968; Boyd et al., 1973) force field calculations for cyclopentadecane also found five low-energy quinquangular conformations, with the [33333] of lowest strain energy (Anet & Rawdah, 1978). The low-temperature 1H and 13C NMR spectra of (II) showed line broadening at the lowest attainable temperatures of 123 and 119 K, respectively, but decoalescence was not observed in either case (Cheng, 1973). Pawar et al. (2008) later recorded the 13C NMR spectra at temperatures to 100.3 K; spectra at the lowest temperatures were substantially more complicated than the two peaks in a ratio of 2:1 expected for the [33333] conformation at slow exchange. This conformation could be present but cannot be the sole conformation populated. In macrocyclic rings, a large number of minimum-energy structures can be populated, due to the existence of a high degree of rotational freedom. For example, 262 low-energy conformations were found within 3 kcal mol-1 by MM2 for cycloheptadecane (Saunders et al., 1990).

The crystal structure of cyclopentadecanone phenylsemicarbazone showed an ordered structure with hydrogen-bonded dimers (van den Hoek et al., 1979), and an unexpected quadrangular conformation, viz. [3435], was found for the C15 ring. An incomplete X-ray study of cyclopentadecanone was reported (Groth, 1976), but no comment on conformation was made. We have recently reported (Noe et al., 2008) the details of the structure of cyclopentadecanone, in which the C15 ring has the quinquangular [13353] conformation. A preliminary X-ray study of cyclopentadecanone oxime indicated that the structure is highly disordered (Groth, 1979).

Although cyclopentadecanone 2,4-dinitrophenylhydrazone, (I), was reported by Brady (1931), no structural data are available in the literature. This paper reports an X-ray analysis of the crystal structure of (I) at 90 K. Representative torsion angles defining the conformation of the 15-membered ring are listed in Table 2. The 15-membered ring is present in a quinquangular [12345] conformation with C1 symmetry, based on the method of Dale (1973). In that system of conformational designation, corner positions are defined, and the numbers of bonds between adjacent corners are listed in brackets, in order of increasing numbers. Corners that are not on adjacent C atoms are readily recognized by having gauche dihedral angles of the same sign on either side. For (I), these are found at ring carbons 2, 6, and 9 in Fig. 1. Adjacent corners may can more difficult to recognize. Using the examples given for cycloundecane, cyclotridecane, and cyclopentadecane by Anet & Rawdah (1978), we also assign carbons 11 and 12 as corners. The dihedral angle centered on these two C atoms is -78.94 (18)°, and the dihedral angles on either side of it are 155.55 (15) and 178.42 (14)°, which would correspond to a gauche bond, surrounded by two that are close to anti. These dihedral angles are similar to the values around the one-bond segment of the [13353] conformation of cyclopentadecane, as calculated by Anet & Rawdah (1978) (166, -78, and 150°). The section of the ring between C12 and C2 is a five-bond segment between corners. Thus, beginning at corner C12 and proceeding clockwise in Fig. 2, the designation in (I) is [12345].

The C1—N1—N2—C16 torsion angle in (I) is -174.11 (15)°. The 2,4-dinitrophenylhydrazone group is nearly planar, with a mean deviation of 0.053 Å for its 14 non-H atoms, and a maximum deviation of 0.208 (1) Å for atom O4. It is nearly perpendicular to the hydrocarbon ring, forming a dihedral angle of 84.66 (1)° with the best plane of the C15 ring. Those 15 C atoms exhibit a mean deviation of 0.382 Å from coplanarity, with a maximum deviation of 0.835 (1) Å for atom C1.

A projection showing intramolecular hydrogen bonding as dashed lines is shown in Fig. 2, which also illustrates close intermolecular O···O contacts between nitro groups [O1···O1(2 - x, -y, 1 - z) = 2.865 (2) Å and O2···O4(-x, 1 - y, 1 - z) = 0.000 (0) Å].

The hydrogen bond is a discrete six-membered ring [graph set S(6); Etter, 1990]. Also evident in Fig. 2 is stacking of the parallel benzene rings related by the inversion center at (1/2, 1/2, 1/2). The interplanar spacing is 3.295 Å, but the rings are slipped, such that the centroid–centroid distance is 3.557 Å.

Related literature top

For related literature, see: Anet & Rawdah (1978); Boyd (1968); Boyd et al. (1973); Brady (1931); Cheng (1973); Dale (1973); Etter (1990); Groth (1976, 1979); Hoek et al. (1979); Saunders et al. (1990).

Experimental top

Cyclopentadecanone 2,4-dinitrophenylhydrazone, (I), was synthesized by treatment of cyclopentadecanone (0.8 g) with a 2,4-dinitrophenylhydrazine solution (12 ml) prepared from 2,4-dinitrophenylhydrazine (1 g), concentrated sulfuric acid (5 ml), water (8 ml), and ethanol (25 ml). The dinitrophenylhydrazone derivative immediately precipitated from the solution, and was isolated by filteration, washed with water, and recrystallized from ethanol [m.p. 373–375 K; literature m.p. 378 K (Brady, 1931)]. The purity of the sample was established by its 13C NMR spectrum.

Refinement top

H atoms on C were placed in calculated positions, guided by difference maps, with C—H bond distances in the range 0.95–0.99° and with Uiso(H) values of 1.2Ueq(C), and thereafter treated as riding. The N—H hydrogen was refined freely.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Displacement ellipsoid plot (50% probability) of cyclopentadecanone 2,4-dinitrophenylhydrazone, (I).
[Figure 2] Fig. 2. The unit cell of (I), showing intramolecular hydrogen bonding and nitro–nitro contacts as dashed lines.
Cyclopentadecanone 2,4-dinitrophenylhydrazone top
Crystal data top
C21H32N4O4Z = 2
Mr = 404.51F(000) = 436
Triclinic, P1Dx = 1.308 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.2486 (14) ÅCell parameters from 4123 reflections
b = 8.3234 (15) Åθ = 2.5–29.3°
c = 17.731 (3) ŵ = 0.09 mm1
α = 103.419 (12)°T = 90 K
β = 94.044 (9)°Lath, yellow
γ = 97.017 (13)°0.33 × 0.10 × 0.02 mm
V = 1027.3 (3) Å3
Data collection top
Nonius KappaCCD with an Oxford Cryosystems Cryostream cooler
diffractometer
3372 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
Graphite monochromatorθmax = 29.3°, θmin = 2.8°
ω scans with κ offsetsh = 99
16738 measured reflectionsk = 1010
4936 independent reflectionsl = 2323
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.104 w = 1/[σ2(Fo2) + (0.0302P)2 + 0.5298P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
4936 reflectionsΔρmax = 0.37 e Å3
266 parametersΔρmin = 0.24 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0153 (16)
Crystal data top
C21H32N4O4γ = 97.017 (13)°
Mr = 404.51V = 1027.3 (3) Å3
Triclinic, P1Z = 2
a = 7.2486 (14) ÅMo Kα radiation
b = 8.3234 (15) ŵ = 0.09 mm1
c = 17.731 (3) ÅT = 90 K
α = 103.419 (12)°0.33 × 0.10 × 0.02 mm
β = 94.044 (9)°
Data collection top
Nonius KappaCCD with an Oxford Cryosystems Cryostream cooler
diffractometer
3372 reflections with I > 2σ(I)
16738 measured reflectionsRint = 0.038
4936 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.37 e Å3
4936 reflectionsΔρmin = 0.24 e Å3
266 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
xyzUiso*/Ueq
O10.87072 (16)0.10477 (14)0.48047 (7)0.0192 (3)
O20.82365 (18)0.18914 (16)0.37503 (7)0.0236 (3)
O30.28483 (19)0.41631 (16)0.31370 (7)0.0272 (3)
O40.10538 (18)0.49862 (15)0.40401 (8)0.0252 (3)
N10.56818 (19)0.14734 (16)0.65874 (8)0.0139 (3)
N20.6406 (2)0.15332 (17)0.58880 (8)0.0135 (3)
H2N0.745 (3)0.117 (2)0.5767 (10)0.016*
N30.77557 (19)0.16912 (16)0.43770 (8)0.0144 (3)
N40.2347 (2)0.42481 (17)0.37939 (9)0.0186 (3)
C10.6738 (2)0.10401 (19)0.70983 (9)0.0135 (3)
C20.5831 (2)0.0806 (2)0.78126 (9)0.0168 (4)
H2A0.58430.03650.78450.020*
H2B0.45080.09770.77440.020*
C30.6735 (2)0.1958 (2)0.85892 (9)0.0161 (4)
H3A0.62690.15040.90200.019*
H3B0.81020.19510.86160.019*
C40.6354 (2)0.3759 (2)0.87123 (10)0.0165 (4)
H4A0.49910.37830.87080.020*
H4B0.67900.42160.82770.020*
C50.7340 (2)0.4855 (2)0.94836 (10)0.0179 (4)
H5A0.86940.47810.94910.021*
H5B0.68760.43970.99140.021*
C60.7079 (3)0.6702 (2)0.96427 (10)0.0202 (4)
H6A0.57320.67730.95470.024*
H6B0.74770.72341.02000.024*
C70.8160 (2)0.7686 (2)0.91478 (10)0.0188 (4)
H7A0.76990.87740.91970.023*
H7B0.79120.70670.85940.023*
C81.0267 (2)0.7994 (2)0.93815 (10)0.0170 (4)
H8A1.06970.69140.93920.020*
H8B1.05190.87190.99160.020*
C91.1408 (3)0.8806 (2)0.88389 (10)0.0177 (4)
H9A1.26910.92220.90950.021*
H9B1.08380.97770.87500.021*
C101.1509 (2)0.7599 (2)0.80525 (10)0.0177 (4)
H10A1.19480.82460.76800.021*
H10B1.02390.70110.78460.021*
C111.2819 (2)0.6303 (2)0.81037 (10)0.0178 (4)
H11A1.41180.68070.80830.021*
H11B1.27560.60130.86130.021*
C121.2348 (2)0.4698 (2)0.74518 (10)0.0161 (4)
H12A1.20540.49990.69530.019*
H12B1.34620.41170.74020.019*
C131.0700 (2)0.3500 (2)0.75891 (10)0.0164 (4)
H13A1.10030.31630.80780.020*
H13B0.95870.40820.76500.020*
C141.0251 (2)0.1951 (2)0.69174 (9)0.0149 (3)
H14A1.14060.14370.68370.018*
H14B0.98940.23070.64390.018*
C150.8694 (2)0.0602 (2)0.70121 (10)0.0155 (4)
H15A0.86160.03560.65540.019*
H15B0.90950.02100.74760.019*
C160.5419 (2)0.21265 (19)0.53597 (9)0.0122 (3)
C170.6019 (2)0.22337 (19)0.46248 (9)0.0131 (3)
C180.5001 (2)0.28929 (19)0.41090 (9)0.0141 (3)
H180.54240.29450.36190.017*
C190.3366 (2)0.3470 (2)0.43182 (10)0.0154 (4)
C200.2703 (2)0.33826 (19)0.50314 (10)0.0158 (4)
H200.15670.37830.51650.019*
C210.3707 (2)0.27143 (19)0.55347 (10)0.0145 (3)
H210.32430.26430.60150.017*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0182 (7)0.0226 (7)0.0196 (6)0.0089 (5)0.0016 (5)0.0079 (5)
O20.0263 (7)0.0317 (7)0.0191 (7)0.0105 (6)0.0107 (6)0.0129 (5)
O30.0281 (8)0.0342 (8)0.0217 (7)0.0052 (6)0.0027 (6)0.0126 (6)
O40.0196 (7)0.0214 (7)0.0358 (8)0.0074 (6)0.0019 (6)0.0087 (6)
N10.0164 (7)0.0128 (7)0.0122 (7)0.0004 (6)0.0025 (6)0.0036 (5)
N20.0126 (7)0.0161 (7)0.0122 (7)0.0035 (6)0.0023 (6)0.0034 (6)
N30.0145 (7)0.0135 (7)0.0151 (7)0.0016 (6)0.0024 (6)0.0031 (6)
N40.0157 (8)0.0150 (7)0.0238 (8)0.0004 (6)0.0041 (6)0.0050 (6)
C10.0154 (9)0.0086 (7)0.0146 (8)0.0018 (6)0.0006 (7)0.0012 (6)
C20.0191 (9)0.0157 (8)0.0165 (9)0.0017 (7)0.0021 (7)0.0059 (7)
C30.0172 (9)0.0182 (8)0.0145 (8)0.0028 (7)0.0021 (7)0.0069 (7)
C40.0158 (9)0.0185 (9)0.0151 (8)0.0023 (7)0.0007 (7)0.0046 (7)
C50.0197 (9)0.0207 (9)0.0133 (9)0.0019 (7)0.0013 (7)0.0047 (7)
C60.0194 (10)0.0221 (9)0.0168 (9)0.0021 (7)0.0024 (7)0.0005 (7)
C70.0199 (10)0.0167 (9)0.0191 (9)0.0042 (7)0.0013 (7)0.0032 (7)
C80.0205 (10)0.0153 (8)0.0142 (8)0.0031 (7)0.0006 (7)0.0018 (7)
C90.0194 (9)0.0141 (8)0.0188 (9)0.0017 (7)0.0002 (7)0.0033 (7)
C100.0191 (9)0.0180 (9)0.0158 (9)0.0011 (7)0.0014 (7)0.0046 (7)
C110.0142 (9)0.0199 (9)0.0173 (9)0.0003 (7)0.0002 (7)0.0026 (7)
C120.0147 (9)0.0178 (9)0.0150 (8)0.0037 (7)0.0009 (7)0.0021 (7)
C130.0158 (9)0.0167 (8)0.0157 (9)0.0017 (7)0.0012 (7)0.0027 (7)
C140.0135 (8)0.0171 (8)0.0144 (8)0.0036 (7)0.0019 (7)0.0039 (7)
C150.0171 (9)0.0133 (8)0.0154 (8)0.0019 (7)0.0004 (7)0.0024 (6)
C160.0135 (8)0.0080 (7)0.0137 (8)0.0012 (6)0.0002 (7)0.0017 (6)
C170.0128 (8)0.0097 (8)0.0146 (8)0.0004 (6)0.0004 (7)0.0001 (6)
C180.0149 (9)0.0121 (8)0.0132 (8)0.0023 (6)0.0013 (7)0.0019 (6)
C190.0139 (9)0.0120 (8)0.0188 (9)0.0005 (7)0.0042 (7)0.0037 (7)
C200.0112 (8)0.0121 (8)0.0221 (9)0.0014 (7)0.0010 (7)0.0008 (7)
C210.0140 (9)0.0134 (8)0.0147 (8)0.0004 (7)0.0031 (7)0.0014 (6)
Geometric parameters (Å, º) top
O1—N31.2420 (17)C8—H8A0.9900
O2—N31.2289 (17)C8—H8B0.9900
O3—N41.2334 (19)C9—C101.530 (2)
O4—N41.2329 (18)C9—H9A0.9900
N1—C11.288 (2)C9—H9B0.9900
N1—N21.3891 (19)C10—C111.535 (2)
N2—C161.356 (2)C10—H10A0.9900
N2—H2N0.869 (18)C10—H10B0.9900
N3—C171.451 (2)C11—C121.534 (2)
N4—C191.459 (2)C11—H11A0.9900
C1—C21.508 (2)C11—H11B0.9900
C1—C151.516 (2)C12—C131.531 (2)
C2—C31.533 (2)C12—H12A0.9900
C2—H2A0.9900C12—H12B0.9900
C2—H2B0.9900C13—C141.522 (2)
C3—C41.526 (2)C13—H13A0.9900
C3—H3A0.9900C13—H13B0.9900
C3—H3B0.9900C14—C151.539 (2)
C4—C51.529 (2)C14—H14A0.9900
C4—H4A0.9900C14—H14B0.9900
C4—H4B0.9900C15—H15A0.9900
C5—C61.535 (2)C15—H15B0.9900
C5—H5A0.9900C16—C211.417 (2)
C5—H5B0.9900C16—C171.421 (2)
C6—C71.526 (2)C17—C181.385 (2)
C6—H6A0.9900C18—C191.375 (2)
C6—H6B0.9900C18—H180.9500
C7—C81.529 (2)C19—C201.399 (2)
C7—H7A0.9900C20—C211.369 (2)
C7—H7B0.9900C20—H200.9500
C8—C91.531 (2)C21—H210.9500
C1—N1—N2116.64 (14)C8—C9—H9B109.1
C16—N2—N1118.84 (13)C10—C9—H9B109.1
C16—N2—H2N118.5 (12)H9A—C9—H9B107.8
N1—N2—H2N122.7 (12)C9—C10—C11113.02 (14)
O2—N3—O1122.26 (13)C9—C10—H10A109.0
O2—N3—C17118.65 (13)C11—C10—H10A109.0
O1—N3—C17119.08 (13)C9—C10—H10B109.0
O4—N4—O3123.67 (14)C11—C10—H10B109.0
O4—N4—C19117.92 (14)H10A—C10—H10B107.8
O3—N4—C19118.39 (14)C12—C11—C10113.54 (14)
N1—C1—C2115.12 (15)C12—C11—H11A108.9
N1—C1—C15126.35 (15)C10—C11—H11A108.9
C2—C1—C15118.28 (14)C12—C11—H11B108.9
C1—C2—C3115.75 (14)C10—C11—H11B108.9
C1—C2—H2A108.3H11A—C11—H11B107.7
C3—C2—H2A108.3C13—C12—C11113.54 (14)
C1—C2—H2B108.3C13—C12—H12A108.9
C3—C2—H2B108.3C11—C12—H12A108.9
H2A—C2—H2B107.4C13—C12—H12B108.9
C4—C3—C2114.20 (13)C11—C12—H12B108.9
C4—C3—H3A108.7H12A—C12—H12B107.7
C2—C3—H3A108.7C14—C13—C12111.64 (14)
C4—C3—H3B108.7C14—C13—H13A109.3
C2—C3—H3B108.7C12—C13—H13A109.3
H3A—C3—H3B107.6C14—C13—H13B109.3
C3—C4—C5111.68 (14)C12—C13—H13B109.3
C3—C4—H4A109.3H13A—C13—H13B108.0
C5—C4—H4A109.3C13—C14—C15116.41 (14)
C3—C4—H4B109.3C13—C14—H14A108.2
C5—C4—H4B109.3C15—C14—H14A108.2
H4A—C4—H4B107.9C13—C14—H14B108.2
C4—C5—C6115.09 (14)C15—C14—H14B108.2
C4—C5—H5A108.5H14A—C14—H14B107.3
C6—C5—H5A108.5C1—C15—C14118.89 (13)
C4—C5—H5B108.5C1—C15—H15A107.6
C6—C5—H5B108.5C14—C15—H15A107.6
H5A—C5—H5B107.5C1—C15—H15B107.6
C7—C6—C5114.39 (14)C14—C15—H15B107.6
C7—C6—H6A108.7H15A—C15—H15B107.0
C5—C6—H6A108.7N2—C16—C21119.99 (14)
C7—C6—H6B108.7N2—C16—C17123.59 (14)
C5—C6—H6B108.7C21—C16—C17116.41 (14)
H6A—C6—H6B107.6C18—C17—C16121.98 (15)
C6—C7—C8112.98 (14)C18—C17—N3116.03 (14)
C6—C7—H7A109.0C16—C17—N3121.98 (14)
C8—C7—H7A109.0C19—C18—C17118.87 (15)
C6—C7—H7B109.0C19—C18—H18120.6
C8—C7—H7B109.0C17—C18—H18120.6
H7A—C7—H7B107.8C18—C19—C20121.52 (15)
C7—C8—C9114.12 (14)C18—C19—N4118.87 (15)
C7—C8—H8A108.7C20—C19—N4119.57 (14)
C9—C8—H8A108.7C21—C20—C19119.28 (15)
C7—C8—H8B108.7C21—C20—H20120.4
C9—C8—H8B108.7C19—C20—H20120.4
H8A—C8—H8B107.6C20—C21—C16121.92 (15)
C8—C9—C10112.57 (14)C20—C21—H21119.0
C8—C9—H9A109.1C16—C21—H21119.0
C10—C9—H9A109.1
C15—C1—C2—C366.69 (18)N2—C16—C17—C18178.05 (16)
C1—C2—C3—C473.82 (18)C21—C16—C17—C180.7 (2)
C2—C3—C4—C5178.22 (14)N2—C16—C17—N30.6 (2)
C3—C4—C5—C6178.25 (15)C21—C16—C17—N3179.36 (14)
C4—C5—C6—C772.9 (2)O2—N3—C17—C182.2 (2)
C5—C6—C7—C871.38 (19)O1—N3—C17—C18178.08 (14)
C6—C7—C8—C9173.55 (14)O2—N3—C17—C16176.59 (15)
C7—C8—C9—C1072.99 (18)O1—N3—C17—C163.2 (2)
C8—C9—C10—C1174.00 (19)C16—C17—C18—C190.4 (2)
C9—C10—C11—C12155.55 (15)N3—C17—C18—C19178.32 (14)
C10—C11—C12—C1378.94 (18)C17—C18—C19—C200.9 (2)
C11—C12—C13—C14178.42 (14)C17—C18—C19—N4176.66 (15)
C12—C13—C14—C15176.39 (14)O4—N4—C19—C18168.96 (15)
C14—C15—C1—C2122.89 (16)O3—N4—C19—C189.5 (2)
C13—C14—C15—C161.5 (2)O4—N4—C19—C208.7 (2)
N1—C1—C15—C1463.3 (2)O3—N4—C19—C20172.85 (15)
C1—N1—N2—C16174.11 (15)C18—C19—C20—C210.3 (2)
N2—N1—C1—C2173.57 (13)N4—C19—C20—C21177.29 (15)
N2—N1—C1—C150.4 (2)C19—C20—C21—C160.9 (2)
N1—C1—C2—C3118.78 (16)N2—C16—C21—C20177.43 (15)
N1—N2—C16—C211.7 (2)C17—C16—C21—C201.3 (2)
N1—N2—C16—C17179.59 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O10.869 (18)1.979 (18)2.6254 (18)130.2 (15)

Experimental details

Crystal data
Chemical formulaC21H32N4O4
Mr404.51
Crystal system, space groupTriclinic, P1
Temperature (K)90
a, b, c (Å)7.2486 (14), 8.3234 (15), 17.731 (3)
α, β, γ (°)103.419 (12), 94.044 (9), 97.017 (13)
V3)1027.3 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.33 × 0.10 × 0.02
Data collection
DiffractometerNonius KappaCCD with an Oxford Cryosystems Cryostream cooler
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
16738, 4936, 3372
Rint0.038
(sin θ/λ)max1)0.689
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.104, 1.01
No. of reflections4936
No. of parameters266
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.37, 0.24

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Selected geometric parameters (Å, º) top
N1—C11.288 (2)N2—C161.356 (2)
N1—N21.3891 (19)
C1—N1—N2116.64 (14)C16—N2—N1118.84 (13)
C15—C1—C2—C366.69 (18)C9—C10—C11—C12155.55 (15)
C1—C2—C3—C473.82 (18)C10—C11—C12—C1378.94 (18)
C2—C3—C4—C5178.22 (14)C11—C12—C13—C14178.42 (14)
C3—C4—C5—C6178.25 (15)C12—C13—C14—C15176.39 (14)
C4—C5—C6—C772.9 (2)C14—C15—C1—C2122.89 (16)
C5—C6—C7—C871.38 (19)C13—C14—C15—C161.5 (2)
C6—C7—C8—C9173.55 (14)N1—C1—C15—C1463.3 (2)
C7—C8—C9—C1072.99 (18)C1—N1—N2—C16174.11 (15)
C8—C9—C10—C1174.00 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O10.869 (18)1.979 (18)2.6254 (18)130.2 (15)
 

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