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In cyclo­trideca­none 2,4-dinitro­phenyl­hydrazone, C19H28N4O4, the 13-membered carbocycle exists in the triangular [337] conformation. The 2,4-dinitro­phenyl­hydrazone group is almost perpendicular to the 13-membered ring, with a dihedral angle of 82.66 (2)° between the mean planes. The dinitro­phenyl­hydrazone rings are packed parallel to each other and separated by 3.28 (1) Å. The NH group forms an intra­molecular hydrogen bond to a nitro O atom, and there is a weaker C—H...O inter­action between a cyclo­tridecane CH group and a symmetry-related 4-nitro O atom, with a C...O distance of 3.436 (2) Å and a 150° angle about the H atom. The structure, in combination with additional evidence, indicates that [337] is the preferred conformation of cyclo­tridecane and other simple 13-membered rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010802012X/gg3158sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010802012X/gg3158Isup2.hkl
Contains datablock I

CCDC reference: 700034

Comment top

The conformations of larger odd-numbered carbocycles such as cyclotridecane are less well characterized than those with an even number of ring atoms. Semiquantitative calculations for eight conformations of cyclotridecane predicted a lowest energy quinquangular [12433] conformation (Dale, 1973). Subsequently, MOLBUILD force-field calculations on five likely conformations and on 1,1-dimethylcyclotridecane suggested a [13333] conformational minimum (Anet & Rawdah, 1978). From experimental studies, low-temperature 1H (127 K) and 13C (123 K) NMR spectra for cyclotridecane show some broadening of resonances, and no information on likely conformers could be extracted (Cheng, 1973). The linewidth for the 1H signal at 127 K was 10 Hz. Several broadened resonances were found in the 13C NMR spectrum at 88 K (Gill et al., 2008).

The X-ray structure of the α,ω-bis (methyldodeca-1,12-diylammonio)hexane dibromide showed a quinquangular [13333] conformation for an ordered model and a similar [13333] and a [346] conformation for a disordered model (Rubin et al., 1984). An X-ray study of the dimethyl-1-hydroxycyclotridecylphosphonate showed two conformations, one of which was the [13333] conformation (Samuel & Weiss, 1969). Two other solid derivatives studied by X-ray crystallography include the cyclotridecanone oxime (II) at 113 K (Groth, 1979) and cyclotridecanone phenylsemicarbazone, (III), at 123 K (Groth, 1980). Both of these crystal structures showed the triangular [337] conformation.

This study reports an X-ray analysis of the crystal structure of (I) at 90 K. As found in (II) and (III), the 13-membered ring is present in a [337] conformation (Fig. 1). In the Dale (1973) system for nomenclature, corner positions are defined as those ring atoms having gauche torsion angles of the same sign on either side. The numbers of bonds between the corners are given in sequence within brackets. The torsion angles for the C13 ring are summarized in Table 1, where C3, C6 and C9 are corners. In (I) and (II), the ring substituent is located on atom C1 (Fig. 1); in (III), the substituent is at an adjacent position (C13). The angle between the mean plane of the 13-ring and the phenyl ring in (I) is 82.66 (2)°. The dinitrophenylhydrazone rings pack parallel to each other around centers at (1, 1, 1/2) and are separated by 3.25 (s.u.?) Å (Fig. 2). The NH group forms an intramolecular hydrogen bond with nitro atom O1, forming a six-membered ring of graph set S(6) (Etter, 1990). Additionally, there is a weaker C—H···O interaction between C7 and O3i, with a C···O distance of 3.436 (2) Å [symmetry code: (i) -x + 2, -y + 2, -z + 1].

The similar macrocyclic ring conformation found for (I), (II) and (III) suggests that the [337] conformation may be preferred. This agrees with the results (Gill et al., 2008) of a stochastic search of cyclotridecane conformational space by MM4. Geminal disubstitution in the dibromide salt and hydroxy phosphonate derivatives described previously may influence their adopted conformations.

Related literature top

For related literature, see: Anet & Rawdah (1978); Cheng (1973); Dale (1973); Etter (1990); Gill et al. (2008); Groth (1979, 1980); Rubin et al. (1984); Samuel & Weiss (1969); Zakharkin et al. (1962).

Experimental top

Compound (I) was synthesized by treatment of cyclotridecanone (0.2 g) with 2,4-dinitrophenylhydrazine solution (3 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 filtration, washed with water, and recrystallized from ethanol [m.p. 377–378 K; literature m.p. 386.7–387.7 K (Zakharkin et al., 1962)]. The yellow blade-shaped crystals were grown by slow evaporation from ethanol.

Refinement top

The H atoms on C were placed in calculated positions, guided by difference maps, with C—H bond distances in the range 0.95–0.99Å and thereafter treated as riding aroms using the SHELXL97 (Sheldrick, 2008) defaults. The N—H hydrogen coordinates were refined. All H displacement parameters were assigned as 1.2Ueq(C or N).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: 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. A displacement ellipsoid plot (at the 50% probability level) of (I).
[Figure 2] Fig. 2. The unit cell of (I).
cyclotridecanone 2,4-dinitrophenylhydrazone top
Crystal data top
C19H28N4O4Z = 2
Mr = 376.45F(000) = 404
Triclinic, P1Dx = 1.318 Mg m3
Hall symbol: -P 1Melting point: 378 K
a = 7.7859 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.8937 (10) ÅCell parameters from 4832 reflections
c = 16.130 (2) Åθ = 2.5–31.5°
α = 81.979 (7)°µ = 0.09 mm1
β = 77.608 (8)°T = 90 K
γ = 80.234 (8)°Lath, yellow
V = 948.7 (2) Å30.40 × 0.08 × 0.03 mm
Data collection top
Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler)
diffractometer
3974 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
Graphite monochromatorθmax = 31.5°, θmin = 2.6°
ω scans with κ offsetsh = 1110
26226 measured reflectionsk = 1111
5518 independent reflectionsl = 2222
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)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0276P)2 + 0.4695P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
5518 reflectionsΔρmax = 0.34 e Å3
248 parametersΔρmin = 0.26 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: 0.0121 (14)
Crystal data top
C19H28N4O4γ = 80.234 (8)°
Mr = 376.45V = 948.7 (2) Å3
Triclinic, P1Z = 2
a = 7.7859 (10) ÅMo Kα radiation
b = 7.8937 (10) ŵ = 0.09 mm1
c = 16.130 (2) ÅT = 90 K
α = 81.979 (7)°0.40 × 0.08 × 0.03 mm
β = 77.608 (8)°
Data collection top
Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler)
diffractometer
3974 reflections with I > 2σ(I)
26226 measured reflectionsRint = 0.029
5518 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.34 e Å3
5518 reflectionsΔρmin = 0.26 e Å3
248 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
O10.64885 (12)0.62443 (12)0.46946 (6)0.0187 (2)
O20.78601 (13)0.72956 (13)0.34616 (6)0.0234 (2)
O31.04660 (13)1.23977 (14)0.30876 (6)0.0276 (2)
O41.02088 (12)1.38929 (12)0.41552 (7)0.0235 (2)
N10.49239 (13)0.85568 (13)0.68070 (6)0.0131 (2)
N20.56946 (13)0.80898 (14)0.59983 (7)0.0129 (2)
H2N0.5568 (19)0.710 (2)0.5812 (9)0.015*
N30.72727 (13)0.73853 (14)0.42281 (7)0.0156 (2)
N40.98689 (14)1.26911 (15)0.38335 (7)0.0185 (2)
C10.40503 (15)0.74620 (16)0.73223 (8)0.0131 (2)
C20.31678 (16)0.80125 (17)0.81914 (8)0.0158 (3)
H2A0.32970.69990.86220.019*
H2B0.18820.83590.81990.019*
C30.38806 (17)0.94988 (17)0.84634 (8)0.0176 (3)
H3A0.30960.98690.89960.021*
H3B0.38321.04920.80160.021*
C40.57951 (17)0.90273 (17)0.86136 (8)0.0170 (3)
H4A0.65340.84430.81260.020*
H4B0.62731.01060.86270.020*
C50.59681 (17)0.78539 (18)0.94393 (8)0.0187 (3)
H5A0.53800.68300.94530.022*
H5B0.53300.84860.99300.022*
C60.78921 (18)0.72372 (18)0.95468 (9)0.0208 (3)
H6A0.85620.82320.93950.025*
H6B0.78950.68211.01550.025*
C70.88498 (17)0.57902 (17)0.89995 (9)0.0179 (3)
H7A0.86490.61120.84090.021*
H7B1.01430.56750.89810.021*
C80.82196 (17)0.40480 (18)0.93381 (9)0.0192 (3)
H8A0.69060.42360.94970.023*
H8B0.86820.36030.98650.023*
C90.87789 (18)0.26630 (17)0.87187 (9)0.0210 (3)
H9A0.83260.15870.90040.025*
H9B1.00930.24140.85900.025*
C100.81163 (17)0.31571 (17)0.78743 (9)0.0187 (3)
H10A0.88920.39400.74970.022*
H10B0.82410.20970.75900.022*
C110.61887 (16)0.40397 (17)0.79641 (8)0.0163 (3)
H11A0.54090.32910.83630.020*
H11B0.60700.51430.82120.020*
C120.55749 (17)0.44035 (17)0.71128 (8)0.0166 (3)
H12A0.53840.33010.69450.020*
H12B0.65320.48570.66730.020*
C130.38514 (16)0.57043 (16)0.71237 (8)0.0149 (2)
H13A0.35080.58190.65600.018*
H13B0.28840.52490.75570.018*
C140.66839 (15)0.91866 (16)0.54556 (8)0.0125 (2)
C150.74814 (15)0.88944 (16)0.45985 (8)0.0129 (2)
C160.84952 (15)1.00571 (17)0.40640 (8)0.0145 (2)
H160.90200.98420.34930.017*
C170.87246 (15)1.15210 (16)0.43761 (8)0.0151 (3)
C180.79480 (16)1.18785 (16)0.52117 (8)0.0153 (3)
H180.81061.29060.54120.018*
C190.69566 (15)1.07289 (16)0.57367 (8)0.0143 (2)
H190.64371.09710.63050.017*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0193 (4)0.0185 (5)0.0183 (5)0.0048 (4)0.0008 (4)0.0036 (4)
O20.0257 (5)0.0298 (6)0.0145 (5)0.0054 (4)0.0014 (4)0.0083 (4)
O30.0274 (5)0.0335 (6)0.0175 (5)0.0068 (4)0.0027 (4)0.0047 (4)
O40.0195 (5)0.0178 (5)0.0316 (6)0.0048 (4)0.0028 (4)0.0017 (4)
N10.0120 (5)0.0151 (5)0.0115 (5)0.0003 (4)0.0016 (4)0.0025 (4)
N20.0135 (5)0.0126 (5)0.0123 (5)0.0016 (4)0.0014 (4)0.0026 (4)
N30.0129 (5)0.0187 (6)0.0149 (5)0.0003 (4)0.0027 (4)0.0039 (4)
N40.0130 (5)0.0192 (6)0.0201 (6)0.0000 (4)0.0030 (4)0.0054 (5)
C10.0105 (5)0.0144 (6)0.0143 (6)0.0006 (4)0.0036 (4)0.0014 (5)
C20.0133 (5)0.0179 (6)0.0153 (6)0.0026 (5)0.0007 (5)0.0029 (5)
C30.0206 (6)0.0150 (6)0.0159 (6)0.0013 (5)0.0003 (5)0.0043 (5)
C40.0192 (6)0.0165 (6)0.0161 (6)0.0056 (5)0.0015 (5)0.0032 (5)
C50.0227 (6)0.0197 (7)0.0138 (6)0.0042 (5)0.0015 (5)0.0037 (5)
C60.0243 (7)0.0227 (7)0.0180 (7)0.0065 (5)0.0073 (5)0.0027 (5)
C70.0165 (6)0.0204 (7)0.0177 (7)0.0060 (5)0.0039 (5)0.0003 (5)
C80.0195 (6)0.0203 (7)0.0187 (7)0.0062 (5)0.0063 (5)0.0032 (5)
C90.0198 (6)0.0165 (7)0.0271 (8)0.0015 (5)0.0089 (5)0.0019 (5)
C100.0185 (6)0.0152 (6)0.0220 (7)0.0009 (5)0.0041 (5)0.0020 (5)
C110.0176 (6)0.0137 (6)0.0177 (6)0.0022 (5)0.0044 (5)0.0009 (5)
C120.0199 (6)0.0132 (6)0.0174 (6)0.0013 (5)0.0050 (5)0.0034 (5)
C130.0154 (6)0.0153 (6)0.0149 (6)0.0036 (5)0.0039 (5)0.0018 (5)
C140.0092 (5)0.0153 (6)0.0123 (6)0.0008 (4)0.0036 (4)0.0006 (5)
C150.0111 (5)0.0139 (6)0.0135 (6)0.0010 (4)0.0041 (4)0.0020 (5)
C160.0102 (5)0.0195 (6)0.0122 (6)0.0015 (5)0.0029 (4)0.0001 (5)
C170.0114 (5)0.0156 (6)0.0162 (6)0.0014 (5)0.0024 (5)0.0044 (5)
C180.0131 (5)0.0133 (6)0.0190 (6)0.0001 (4)0.0045 (5)0.0008 (5)
C190.0126 (5)0.0147 (6)0.0145 (6)0.0004 (4)0.0018 (4)0.0023 (5)
Geometric parameters (Å, º) top
O1—N31.2453 (14)C7—H7A0.9900
O2—N31.2302 (14)C7—H7B0.9900
O3—N41.2323 (15)C8—C91.530 (2)
O4—N41.2332 (15)C8—H8A0.9900
N1—C11.2871 (16)C8—H8B0.9900
N1—N21.3859 (14)C9—C101.5357 (19)
N2—C141.3545 (16)C9—H9A0.9900
N2—H2N0.899 (15)C9—H9B0.9900
N3—C151.4520 (16)C10—C111.5294 (18)
N4—C171.4600 (16)C10—H10A0.9900
C1—C131.5067 (17)C10—H10B0.9900
C1—C21.5104 (17)C11—C121.5236 (18)
C2—C31.5317 (18)C11—H11A0.9900
C2—H2A0.9900C11—H11B0.9900
C2—H2B0.9900C12—C131.5436 (18)
C3—C41.5365 (18)C12—H12A0.9900
C3—H3A0.9900C12—H12B0.9900
C3—H3B0.9900C13—H13A0.9900
C4—C51.5298 (18)C13—H13B0.9900
C4—H4A0.9900C14—C191.4198 (17)
C4—H4B0.9900C14—C151.4221 (17)
C5—C61.5335 (19)C15—C161.3934 (17)
C5—H5A0.9900C16—C171.3754 (18)
C5—H5B0.9900C16—H160.9500
C6—C71.5329 (19)C17—C181.4001 (18)
C6—H6A0.9900C18—C191.3708 (17)
C6—H6B0.9900C18—H180.9500
C7—C81.5279 (18)C19—H190.9500
C1—N1—N2116.91 (10)C7—C8—H8B108.5
C14—N2—N1118.09 (10)C9—C8—H8B108.5
C14—N2—H2N118.2 (9)H8A—C8—H8B107.5
N1—N2—H2N123.7 (9)C8—C9—C10114.42 (11)
O2—N3—O1122.56 (11)C8—C9—H9A108.7
O2—N3—C15118.57 (11)C10—C9—H9A108.7
O1—N3—C15118.87 (10)C8—C9—H9B108.7
O3—N4—O4123.97 (11)C10—C9—H9B108.7
O3—N4—C17118.08 (11)H9A—C9—H9B107.6
O4—N4—C17117.93 (11)C11—C10—C9114.84 (11)
N1—C1—C13125.20 (11)C11—C10—H10A108.6
N1—C1—C2116.31 (11)C9—C10—H10A108.6
C13—C1—C2118.49 (10)C11—C10—H10B108.6
C1—C2—C3115.78 (10)C9—C10—H10B108.6
C1—C2—H2A108.3H10A—C10—H10B107.5
C3—C2—H2A108.3C12—C11—C10112.42 (11)
C1—C2—H2B108.3C12—C11—H11A109.1
C3—C2—H2B108.3C10—C11—H11A109.1
H2A—C2—H2B107.4C12—C11—H11B109.1
C2—C3—C4113.67 (11)C10—C11—H11B109.1
C2—C3—H3A108.8H11A—C11—H11B107.9
C4—C3—H3A108.8C11—C12—C13114.12 (11)
C2—C3—H3B108.8C11—C12—H12A108.7
C4—C3—H3B108.8C13—C12—H12A108.7
H3A—C3—H3B107.7C11—C12—H12B108.7
C5—C4—C3114.05 (11)C13—C12—H12B108.7
C5—C4—H4A108.7H12A—C12—H12B107.6
C3—C4—H4A108.7C1—C13—C12112.53 (10)
C5—C4—H4B108.7C1—C13—H13A109.1
C3—C4—H4B108.7C12—C13—H13A109.1
H4A—C4—H4B107.6C1—C13—H13B109.1
C4—C5—C6114.09 (11)C12—C13—H13B109.1
C4—C5—H5A108.7H13A—C13—H13B107.8
C6—C5—H5A108.7N2—C14—C19119.68 (11)
C4—C5—H5B108.7N2—C14—C15123.60 (11)
C6—C5—H5B108.7C19—C14—C15116.73 (11)
H5A—C5—H5B107.6C16—C15—C14121.58 (11)
C7—C6—C5113.69 (11)C16—C15—N3116.27 (11)
C7—C6—H6A108.8C14—C15—N3122.14 (11)
C5—C6—H6A108.8C17—C16—C15118.95 (12)
C7—C6—H6B108.8C17—C16—H16120.5
C5—C6—H6B108.8C15—C16—H16120.5
H6A—C6—H6B107.7C16—C17—C18121.64 (11)
C8—C7—C6112.77 (11)C16—C17—N4119.05 (11)
C8—C7—H7A109.0C18—C17—N4119.26 (11)
C6—C7—H7A109.0C19—C18—C17119.25 (12)
C8—C7—H7B109.0C19—C18—H18120.4
C6—C7—H7B109.0C17—C18—H18120.4
H7A—C7—H7B107.8C18—C19—C14121.84 (12)
C7—C8—C9115.28 (11)C18—C19—H19119.1
C7—C8—H8A108.5C14—C19—H19119.1
C9—C8—H8A108.5
C1—N1—N2—C14177.27 (11)C19—C14—C15—C160.62 (17)
N2—N1—C1—C131.98 (17)N2—C14—C15—N30.94 (18)
C13—C1—C2—C3161.03 (11)C19—C14—C15—N3178.70 (10)
C2—C1—C13—C12106.70 (12)O2—N3—C15—C166.00 (16)
C1—C2—C3—C467.14 (15)O1—N3—C15—C16174.88 (10)
C2—C3—C4—C574.04 (14)O2—N3—C15—C14173.35 (11)
C3—C4—C5—C6174.27 (11)O1—N3—C15—C145.76 (16)
C4—C5—C6—C776.56 (15)C14—C15—C16—C170.04 (17)
C5—C6—C7—C873.64 (15)N3—C15—C16—C17179.32 (10)
C6—C7—C8—C9165.98 (11)C15—C16—C17—C180.80 (18)
C7—C8—C9—C1059.54 (15)C15—C16—C17—N4176.53 (11)
C8—C9—C10—C1142.72 (16)O3—N4—C17—C166.15 (17)
C9—C10—C11—C12176.67 (11)O4—N4—C17—C16172.37 (11)
C10—C11—C12—C13164.47 (10)O3—N4—C17—C18176.45 (11)
C11—C12—C13—C161.91 (14)O4—N4—C17—C185.03 (16)
N2—N1—C1—C2178.08 (10)C16—C17—C18—C191.02 (18)
N1—C1—C2—C318.92 (16)N4—C17—C18—C19176.30 (11)
N1—C1—C13—C1273.25 (16)C17—C18—C19—C140.40 (18)
N1—N2—C14—C192.39 (16)N2—C14—C19—C18179.95 (11)
N1—N2—C14—C15177.24 (10)C15—C14—C19—C180.39 (17)
N2—C14—C15—C16179.74 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O10.899 (15)1.961 (15)2.6302 (14)129.9 (12)
C7—H7A···O3i0.992.543.4363 (18)150
Symmetry code: (i) x+2, y+2, z+1.

Experimental details

Crystal data
Chemical formulaC19H28N4O4
Mr376.45
Crystal system, space groupTriclinic, P1
Temperature (K)90
a, b, c (Å)7.7859 (10), 7.8937 (10), 16.130 (2)
α, β, γ (°)81.979 (7), 77.608 (8), 80.234 (8)
V3)948.7 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.40 × 0.08 × 0.03
Data collection
DiffractometerNonius KappaCCD (with an Oxford Cryosystems Cryostream cooler)
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
26226, 5518, 3974
Rint0.029
(sin θ/λ)max1)0.735
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.099, 1.01
No. of reflections5518
No. of parameters248
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.34, 0.26

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 torsion angles (º) top
C1—N1—N2—C14177.27 (11)C5—C6—C7—C873.64 (15)
N2—N1—C1—C131.98 (17)C6—C7—C8—C9165.98 (11)
C13—C1—C2—C3161.03 (11)C7—C8—C9—C1059.54 (15)
C2—C1—C13—C12106.70 (12)C8—C9—C10—C1142.72 (16)
C1—C2—C3—C467.14 (15)C9—C10—C11—C12176.67 (11)
C2—C3—C4—C574.04 (14)C10—C11—C12—C13164.47 (10)
C3—C4—C5—C6174.27 (11)C11—C12—C13—C161.91 (14)
C4—C5—C6—C776.56 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O10.899 (15)1.961 (15)2.6302 (14)129.9 (12)
C7—H7A···O3i0.992.543.4363 (18)150
Symmetry code: (i) x+2, y+2, z+1.
 

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