Structural similarities among eight benzoyl­hydrazones

The crystal structures of eight benzoyl­hydrazones with different substituents have been investigated, namely 1-benzoyl-2-(propan-2-yl­idene)hydrazone, C₁₀H₁₂N₂O, (I), 1-benzoyl-2-(1-cyclo­hexyl­ethyl­idene)hydrazone, C₁₅H₂₀N₂O, (II), 1-benzoyl-2-[1-(naphthalen-2-yl)ethyl­idene]hydrazone, C₁₉H₁₆N₂O, (III), 1-benzoyl-2-(1-cyclo­hexyl­benzyl­idene)hydrazone, C₂₀H₂₂N₂O, (IV), 1-benzoyl-2-(1-phenyl­benzyl­idene)hydrazone, C₂₀H₁₆N₂O, (V), 1-benzoyl-2-[1-(4-chloro­phen­yl)benzyl­idene]hydrazone, C₂₀H₁₅ClN₂O, (VI), 1-ben­zoyl-2-(4-hy­droxy­benzyl­idene)hydrazone methanol monosolvate, C₁₄H₁₂N₂O₂·CH₃OH, (VII), and 1-benzoyl-2-(1,1-di­phenyl­propan-2-yl­idene)hydrazone, C₂₂H₂₀N₂O, (VIII). The ten mol­ecules in the eight crystal structures [there are two independent mol­ecules in the structures of (V) and (VI)] show similar conformations and hydrogen-bonding patterns. The C=N—NH—C=O group is planar, but the plane of the phenyl ring of the benzoyl group is rotated by about 30° with respect to that of the keto group [except for (IV), where the groups are coplanar]. Only in the amide group of (VIII) is the N—H group syn to the C=O bond, whereas the seven other compounds exhibit the anti conformation. Unless prevented by steric hindrance, N—H...O hydrogen bonds help to stabilize the crystal structure, which leads to infinite chains or dimers depending upon the mol­ecular conformation. The mol­ecular packing is supported by inter­molecular C—H...O inter­actions. In the crystal structure of (VII), the methanol solvent mol­ecule participates in two strong hydrogen bonds and two weak C—H...O inter­actions, thus acting as a link between the mol­ecular chains.

S1. Introduction

Hydrazones are important derivatives of carbonyl compounds; they are easy to synthesize and have been used for a long time for the identification and characterization of aldehydes and ketones. In addition, N-acyl­hydrazones are versatile electrophiles for the synthesis of nitro­gen-containing compounds, since their molecular structure provides a suitable template for the chelation of Lewis acids, which activate the imino C atom as a target for nucleophilic attack (Sugiura & Kobayashi, 2005). They also play an important role in the catalytic asymmetric reductive amination of ketones via highly enanti­oselective hydrogenation of the C═N double bond (Burk et al., 1994). One characteristic feature of N-acyl­hydrazones is the presence of an amide next to an imine group, so that one donor (N—H) and two acceptor groups (C═O and C═N) are able to participate in hydrogen bonds. The two preferred conformations of the amide group (syn or anti) give rise to different hydrogen-bonding patterns: the syn conformation allows the formation of dimers connected by two N—H···O bonds, whereas the anti conformation tends to favour chains of molecules. We have studied eight benzoyl­hydrazones, (I)–(VIII), with different substituents R₁ and R₂ (which are anti- or synperiplanar to the amide N atom, respectively); they were readily obtained by a condensation reaction from benzoyl­hydrazine (benzoic acid hydrazide) and a suitable aldehyde or ketone.

S2. Experimental

S2.1. Synthesis and crystallization

All eight compounds were synthesized by a similar procedure. A 1:1 mixture of the reaction components (0.01 mol), a small amount of dried sodium sulfate and an adequate volume (5–20 ml) of a suitable solvent were added to a 100 ml flask. If the reaction did not proceed, one drop of concentrated sulfuric acid was added. The mixture was stirred overnight at room temperature. After purification, each product was characterized by IR, NMR and mass spectroscopy (Ton, 2004), and crystallized as colourless blocks from di­chloro­methane [for (I), (II), (III) and (VIII)], di­ethyl ether [for (IV) and (V)], tetra­hydro­furan [for (VI)] or methanol [for (VII)] by slow evaporation of the solvent at room temperature.

S2.2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. All H atoms in (I)–(VIII) were unequivocally located by difference Fourier synthesis. Subsequently, C-bound H atoms were refined using a riding model, with C—H = 0.98 (methyl), 0.99 (methyl­ene), 1.00 (methine) and 0.95 Å (aromatic), but methyl groups were allowed to rotate about their local threefold axis. O- and N-bound H atoms were refined isotropically. For all riding H atoms, fixed individual displacement parameters were employed, with U_iso(H) = 1.5U_eq(C) for methyl or 1.2U_eq(C) for the other H atoms. Since the isotropic displacement parameter of the H atom bonded to N1' in (VI) was significantly lower than the U_eq(N) value it was also refined with U_iso(H1') = 1.2U_eq(N1').

In (IV) and (VIII), the refinement of an extinction coefficient improved the agreement between structure model and experimental data significantly. The crystal of (VI) showing similar lengths for a and c was a pseudomerohedral twin (twin law: 001/010/100). All reflections overlap and could be integrated using the same orientation matrix. The contribution of the major component refined to 0.6819 (6).

S3. Comment

The structures of compounds (I)–(III), which differ only in the R₁ substituent (methyl, cyclo­hexyl or naphthalen-2-yl), show many common features. The hydrazone group of (I) including the two methyl substituents is planar, but the phenyl ring is rotated by 34 (2)° with respect to the C═O bond (Fig. 1). Replacement of one methyl group by a cyclo­hexyl [in (II)] or a naphthalen-2-yl [in (III)] substituent does not change the molecular conformation significantly. While the naphthyl group in (III) is coplanar with the C═N—NH—C═O group, the phenyl ring of the benzoyl group is again rotated by 39.0 (7) [in (II)] and 23.9 (2)° [in (III)] (Figs. 2 and 3). In all three compounds, the anti conformation of the amide group gives rise to the formation of infinite chains held together by inter­molecular N—H···O hydrogen bonds between molecules related by a glide plane [in (I) and (II)] or by translation along a [in (III)] (Tables 2–4). These chains are further stabilized by short C—H···O contacts, especially from the methyl group which is syn to N1 (Figs. 4–6). In (I) there is also a short inter­molecular N—H···N contact between the amide and imine groups. In the crystal packing of (I)–(III), no direct stacking of aromatic rings is observed, although they are almost parallel, which gives rise to layer-like arrangements.

In contrast with (I)–(III), compounds (IV)–(VI) possess a phenyl ring instead of a methyl group as R₂ substituent. Replacement of the methyl group in (II) by a phenyl ring leads to (IV), where two phenyl rings shield the N—H group, thus preventing the formation of an N—H···O bond, but several C—H···O inter­actions from the aromatic rings to the C═O group stabilize the packing (Figs. 7 and 8; Table 5). The two phenyl rings are perpendicular to each other [angle 88 (2)°], but in contrast with (I)–(III) the phenyl ring of the benzoyl group is coplanar with the hydrazone group [angle 4(2)°]. If the cyclo­hexyl substituent is also replaced by a phenyl group, a benzoyl­hydrazone with three phenyl rings is formed, (V). The two independent molecules (both with an anti amide group) show similar conformations, with the phenyl ring of the benzoyl group rotated by 25.2 (9) and 26.1 (10)° with respect to the C═O bond. However, one of the phenyl rings of the second molecule (atoms C21'–C26') is almost perpendicular [89 (2)°] to the hydrazone group (Fig. 9). As in (IV), the bulky substituents prevent the formation of hydrogen-bonded chains, but one N—H···O hydrogen bond between the two independent molecules is observed (Fig. 10 and Table 6).

Compound (VI) differs from (V) only by a 4-chloro substituent at one phenyl ring. Both compounds crystallize in the same space group P2₁/n, but the cell constants are rather different. The two independent molecules of (VI) show similar conformations: an anti amide group with rotations of the aromatic rings by 21.3 (10)/34.8 (18) (benzoyl), 15.5 (8)/24.7 (10) (4-chloro­phenyl) and 66.4 (9)/67.3 (13)° (unsubstituted phenyl substituent) with respect to the hydrazone group (Fig. 11); a least-squares fit of all non-H atoms shows an r.m.s. deviation of 0.145 Å. The conformations of the two molecules of (VI) compare reasonably well with those of (V) except for the unsubstituted phenyl ring, the orientation of which is different. Without this ring, the four pairwise fits between (V) and (VI) show r.m.s. deviations between 0.433 and 0.542 Å. Like in (IV) and (V), the phenyl rings prevent the formation of N—H···O hydrogen-bonded molecular chains, but several C—H···O contacts from the phenyl rings to the keto groups help to stabilize the packing (Fig. 12 and Table 7). Apart from steric arguments, the absence of chains formed by N—H···O hydrogen bonds, which would be favoured by cooperative effects (Steiner, 2002), in the structures of (IV), (V) and (VI) can also be explained by the formation of N—H···π hydrogen bonds to the neighbouring phenyl rings. This view is supported by H···π distances of about 3.05 Å to the ring centroid and N—H···π angles of approximately 130° for the five N—H groups in (IV)–(VI), in agreement with the geometric conditions defined by Malone et al. (1997).

Whereas the seven other benzoyl­hydrazones were prepared from a ketone, compound (VII) was synthesized from an aldehyde. The 4-hy­droxy­phenyl ring is coplanar with the C═N—NH—C═O group (again in the anti conformation) but the phenyl ring of the benzoyl group is rotated by 22.8 (10)° (Fig. 13). A methanol solvent molecule participates in two hydrogen bonds (N—H···O and O—H···O), thus linking the N—H and C═O groups of neighbouring molecules. In addition, the keto group accepts a second hydrogen bond from the O—H substituent, which also inter­acts with atom N2. Short C—H···O contacts to both O—H groups further contribute to the stabilization of the crystal packing (Fig. 14 and Table 8). Two pseudo-polymorphs of this hydrazone have already been published, viz. a di­methyl­formamide (DMF) monosolvate [Cambridge Structural Database (CSD, Version 5.35 of November 2013 plus two updates; Allen, 2002) refcode JAXQEF; Jing et al., 2005] and a monohydrate (CSD refcode WIPFEH; Tai et al., 2007), which both crystallize in the same Pbca space group but are not isostructural with (VII). Both structures exhibit the anti conformation of the amide group. In the DMF monosolvate, in which the molecules form chains with the aid of (O,N)—H···(O,N) hydrogen bonds, the phenyl ring of the benzoyl group is rotated by only about 10° with respect to the keto group, while this value is approximately 35° in the monohydrate. In the latter structure, the water molecule plays a prominent role and participates in all hydrogen bonds (one N—H···O and three O—H···O, two of them to symmetry-equivalent carbonyl O atoms and one from the O—H group of the 4-hy­droxy­phenyl ring).

In compound (VIII), the aromatic ring of the benzoyl group is also rotated with respect to the planar hydrazone group [angle 35 (2)°]. However, in contrast with (I)–(VII) this compound exhibits a syn conformation of the amide group, with the methyl group at C2 synperiplanar to N1, whereas the phenyl rings of the large di­phenyl­methyl substituent point away from the amide group (Fig. 15). This enables the formation of a hydrogen-bonded dimer across an inversion centre [with an R₂²(8) pattern, according to the notation of Bernstein et al. (1995)], which is further stabilized by short C—H···O contacts from the neighbouring methyl groups (Fig. 16 and Table 9).

A comparison of these eight structures shows that, in most cases, the phenyl ring of the benzoyl group is rotated with respect to the C═O bond, which makes it easier for a hydrogen-bond acceptor to approach the N—H group. Consequently, the benzoyl group is planar when a large substituent prevents such an approach (cf. Fig. 7). In the absence of steric crowding, each N—H group is involved in an inter­molecular hydrogen bond to the keto group [or in (VII) to the solvent], occasionally supported by an inter­action with the neighbouring imine (cf. Fig. 4), which can be inter­preted as the minor component of a bifurcated hydrogen bond. In addition, a number of short C—H···O contacts are present. Another stabilizing factor of the crystal packing is partial stacking of aromatic rings (cf. Figs. 8 and 12), whereas direct parallel stacking is never observed.

A search of the CSD yielded 121 structures of benzoyl­hydrazones with an unsubstituted benzoyl group and no additional cyclic bonds. Only five of them [CSD refcodes CAVPEU (Baker et al., 1983), COFGOU (Ni et al., 2008), EXINEF01 (Singh et al., 2011), TUMDIP01 (López-Torres & Mendiola, 2009) and WENVUH (Ali et al., 2006)] show a syn amide and form an R₂²(8) pattern with two N—H···O hydrogen bonds, while the other structures exhibit the anti conformation. Also, the orientation of the phenyl ring of the benzoyl group with respect to the hydrazone group (torsion angles 0–48°, usually around 30°) and the packing motifs (syn = dimer; anti = tendeny to form chains; solvent molecules bridge amide groups via hydrogen bonds) agree well with the gross structural features of (I)–(VIII).

The situation is quite different if strong hydrogen-bond donor and acceptor groups within the molecule compete with N—H and C═O. One example are the isonicotinoylhydrazones, in which the phenyl is replaced by a pyridyl group (Wardell et al., 2007). These structures also show a planar hydrazone group, but there is a clear preference for the pyridyl N atom (instead of the C═O group) to act as a hydrogen-bond acceptor. Therefore, the supra­molecular aggregation is more complex than in the structures of the benzoyl­hydrazones (I)–(VIII). Also, the inter­molecular arrangement in the structures of 1-benzoyl-2-benzyl­idenehydrazones in which the phenyl ring of the benzoyl group is substituted by a 4-hy­droxy group is clearly different, not just because of the formation of additional O—H···O or O—H···N hydrogen bonds from the O—H substituent; here the molecules really stack head-to-tail or head-to-head and form two-dimensional networks (Subashini et al., 2012).

Why do some N-acyl­hydrazones adopt a syn instead of the favoured anti conformation? Is this an intrinsic tendency which arises from the molecular constitution or is the crystal packing responsible for it? These questions are difficult to answer in the case of the benzoyl­hydrazones since the bulky phenyl groups strongly influence the molecular packing. Therefore, we have systematically investigated a number of simpler hydrazones where we have found some rules concerning the conformation of the amide group (Degen et al., 2015).

Related literature

For related literature, see: Ali et al. (2006); Allen (2002); Baker et al. (1983); Bernstein et al. (1995); Burk et al. (1994); Degen et al. (2015); Jing et al. (2005); López-Torres & Mendiola (2009); Malone et al. (1997); Ni et al. (2008); Singh et al. (2011); Steiner (2002); Subashini et al. (2012); Sugiura & Kobayashi (2005); Tai et al. (2007); Ton (2004); Wardell et al. (2007).

Computing details

For all compounds, data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008) and XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures

	Fig. 1. A perspective view of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A perspective view of (II), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 3. A perspective view of (III), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 4. A packing diagram for (I), viewed along the b axis. Hydrogen bonds (black) and short C—H···O contacts (cyan) are shown as dotted lines. The H atoms of the phenyl groups have been omitted. [Symmetry code: (i) x, -y + 3/2, z + 1/2.]
	Fig. 5. A packing diagram for (II), viewed along the b axis. Hydrogen bonds (black) and short C—H···O contacts (cyan) are shown as dotted lines. The H atoms of the phenyl and cyclohexyl groups have been omitted. [Symmetry code: (i) x, -y + 1/2, z + 1/2.]
	Fig. 6. A partial packing diagram for (III). Hydrogen bonds (black) and short C—H···O contacts (cyan) are shown as dotted lines. For a full packing diagram, see extra figure in the Supporting information. [Symmetry codes: (i) x + 1, y, z; (ii) -x + 1, -y + 1, -z.]
	Fig. 7. A perspective view of (IV), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 8. A partial packing diagram for (IV). Short C—H···O contacts are shown as dotted lines. For a full packing diagram, see extra figure in the Supporting information. [Symmetry codes: (i) -x + 1/2, y + 1/2, -z + 1/2; (ii) -x + 1/2, -y + 3/2, -z; (iii) -x + 1, y, -z + 1/2.]
	Fig. 9. Perspective views of (a) the first molecule and (b) the second molecule of (V), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 10. A partial packing diagram for (V). Hydrogen bonds (black) and short C—H···O contacts (cyan) are shown as dotted lines. For a full packing diagram, see extra figure in the Supporting information. [Symmetry code: (i) -x + 1, -y + 2, -z.]
	Fig. 11. Perspective views of (a) the first molecule and (b) the second molecule of (VI), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 12. A partial packing diagram for (VI). Short C—H···O contacts are shown as dotted lines. For a full packing diagram, see extra figure in the Supporting information. [Symmetry codes: (i) -x + 1, -y + 1, -z; (ii) x - 1/2, -y + 1/2, z - 1/2; (iii) -x + 1, -y, -z + 1; (iv) x, y - 1, z.]
	Fig. 13. A perspective view of (VII), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The O—H···O hydrogen bond from the methanol solvent molecule is shown as a dashed line.
	Fig. 14. A partial packing diagram for (VII). Hydrogen bonds (black) and short C—H···O contacts (cyan) are shown as dotted lines. For a full packing diagram, see extra figure in the Supporting information. [Symmetry codes: (i) -x + 1/2, y - 1/2, z; (ii) -x, y - 1/2, -z + 3/2; (iii) -x, y + 1/2, -z + 3/2.]
	Fig. 15. A perspective view of (VIII), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 16. A partial packing diagram for (VIII). Hydrogen bonds (black) and short C—H···O (cyan) and C—H···N (blue) contacts are shown as dotted lines. For a full packing diagram, see extra figure in the Supporting information. [Symmetry codes: (i) -x + 1, -y + 2, -z; (ii) x + 1/2, -y + 3/2, z - 1/2.]

(I) 1-Benzoyl-2-(propan-2-ylidene)hydrazone

Crystal data

C10H12N2O	Z = 4
Mr = 176.22	F(000) = 376
Monoclinic, P21/c	Dx = 1.257 Mg m^−3
a = 7.6950 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 17.129 (1) Å	µ = 0.08 mm^−1
c = 7.8316 (8) Å	T = 173 K
β = 115.525 (8)°	Block, colourless
V = 931.51 (15) Å^3	0.47 × 0.21 × 0.20 mm

Data collection

Stoe IPDS II two-circle diffractometer	1443 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.056
Graphite monochromator	θmax = 26.5°, θmin = 2.9°
φ scans	h = −9→9
18245 measured reflections	k = −21→21
1929 independent reflections	l = −9→9

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ^2(Fo^2) + (0.062P)^2] where P = (Fo^2 + 2Fc^2)/3
1929 reflections	(Δ/σ)max = 0.001
124 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.22954 (15)	0.84831 (5)	0.23713 (12)	0.0504 (3)
N1	0.17395 (13)	0.74071 (6)	0.37381 (14)	0.0344 (2)
H1	0.1758 (19)	0.7193 (8)	0.475 (2)	0.043 (4)*
N2	0.04325 (13)	0.71503 (6)	0.19575 (13)	0.0365 (2)
C1	0.25616 (16)	0.81092 (7)	0.37968 (16)	0.0357 (3)
C2	−0.00615 (16)	0.64339 (7)	0.17855 (16)	0.0358 (3)
C3	0.0664 (2)	0.58229 (7)	0.32874 (19)	0.0486 (3)
H3A	0.2058	0.5765	0.3735	0.073*
H3B	0.0029	0.5325	0.2768	0.073*
H3C	0.0381	0.5978	0.4346	0.073*
C4	−0.14684 (19)	0.61897 (8)	−0.01587 (19)	0.0483 (3)
H4A	−0.1655	0.6619	−0.1048	0.072*
H4B	−0.2703	0.6058	−0.0147	0.072*
H4C	−0.0968	0.5732	−0.0552	0.072*
C11	0.39024 (15)	0.84070 (6)	0.57065 (15)	0.0336 (3)
C12	0.50952 (17)	0.79238 (7)	0.71591 (17)	0.0388 (3)
H12	0.5031	0.7374	0.6985	0.047*
C13	0.63808 (18)	0.82412 (8)	0.88634 (18)	0.0457 (3)
H13	0.7207	0.7910	0.9854	0.055*
C14	0.64574 (19)	0.90401 (8)	0.91180 (19)	0.0488 (3)
H14	0.7324	0.9256	1.0296	0.059*
C15	0.52895 (19)	0.95269 (8)	0.7680 (2)	0.0494 (3)
H15	0.5351	1.0076	0.7865	0.059*
C16	0.40294 (18)	0.92116 (7)	0.59707 (18)	0.0411 (3)
H16	0.3243	0.9546	0.4968	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0736 (6)	0.0411 (5)	0.0303 (4)	−0.0044 (4)	0.0166 (4)	0.0055 (4)
N1	0.0400 (5)	0.0367 (5)	0.0226 (5)	−0.0016 (4)	0.0099 (4)	0.0004 (4)
N2	0.0371 (5)	0.0416 (6)	0.0254 (5)	0.0010 (4)	0.0083 (4)	−0.0021 (4)
C1	0.0417 (6)	0.0341 (6)	0.0300 (6)	0.0041 (5)	0.0143 (5)	0.0018 (5)
C2	0.0356 (5)	0.0402 (6)	0.0308 (6)	0.0031 (5)	0.0136 (5)	−0.0028 (5)
C3	0.0590 (7)	0.0410 (7)	0.0391 (7)	−0.0007 (6)	0.0150 (6)	−0.0004 (5)
C4	0.0488 (7)	0.0471 (7)	0.0378 (7)	−0.0035 (5)	0.0081 (6)	−0.0076 (6)
C11	0.0364 (5)	0.0349 (6)	0.0308 (6)	−0.0009 (4)	0.0158 (5)	0.0001 (4)
C12	0.0422 (6)	0.0354 (6)	0.0351 (6)	−0.0021 (5)	0.0131 (5)	0.0011 (5)
C13	0.0423 (6)	0.0487 (7)	0.0361 (6)	−0.0036 (5)	0.0075 (5)	0.0029 (5)
C14	0.0473 (7)	0.0519 (7)	0.0389 (7)	−0.0112 (6)	0.0105 (6)	−0.0098 (6)
C15	0.0562 (7)	0.0374 (6)	0.0501 (8)	−0.0069 (5)	0.0187 (6)	−0.0087 (6)
C16	0.0458 (6)	0.0350 (6)	0.0400 (6)	0.0001 (5)	0.0160 (5)	0.0003 (5)

Geometric parameters (Å, º)

O1—C1	1.2253 (14)	C4—H4C	0.9800
N1—C1	1.3505 (15)	C11—C12	1.3863 (16)
N1—N2	1.3931 (13)	C11—C16	1.3907 (16)
N1—H1	0.868 (16)	C12—C13	1.3849 (17)
N2—C2	1.2745 (15)	C12—H12	0.9500
C1—C11	1.4939 (16)	C13—C14	1.3804 (19)
C2—C3	1.4915 (17)	C13—H13	0.9500
C2—C4	1.4983 (16)	C14—C15	1.378 (2)
C3—H3A	0.9800	C14—H14	0.9500
C3—H3B	0.9800	C15—C16	1.3805 (18)
C3—H3C	0.9800	C15—H15	0.9500
C4—H4A	0.9800	C16—H16	0.9500
C4—H4B	0.9800
C1—N1—N2	116.15 (10)	H4A—C4—H4C	109.5
C1—N1—H1	121.5 (9)	H4B—C4—H4C	109.5
N2—N1—H1	120.1 (9)	C12—C11—C16	119.36 (11)
C2—N2—N1	117.62 (10)	C12—C11—C1	123.03 (10)
O1—C1—N1	122.86 (11)	C16—C11—C1	117.47 (10)
O1—C1—C11	120.39 (10)	C13—C12—C11	120.13 (11)
N1—C1—C11	116.71 (10)	C13—C12—H12	119.9
N2—C2—C3	126.80 (11)	C11—C12—H12	119.9
N2—C2—C4	115.35 (11)	C14—C13—C12	119.78 (12)
C3—C2—C4	117.81 (11)	C14—C13—H13	120.1
C2—C3—H3A	109.5	C12—C13—H13	120.1
C2—C3—H3B	109.5	C15—C14—C13	120.64 (12)
H3A—C3—H3B	109.5	C15—C14—H14	119.7
C2—C3—H3C	109.5	C13—C14—H14	119.7
H3A—C3—H3C	109.5	C14—C15—C16	119.60 (12)
H3B—C3—H3C	109.5	C14—C15—H15	120.2
C2—C4—H4A	109.5	C16—C15—H15	120.2
C2—C4—H4B	109.5	C15—C16—C11	120.46 (12)
H4A—C4—H4B	109.5	C15—C16—H16	119.8
C2—C4—H4C	109.5	C11—C16—H16	119.8
C1—N1—N2—C2	165.72 (10)	C16—C11—C12—C13	0.85 (17)
N2—N1—C1—O1	−4.91 (16)	C1—C11—C12—C13	176.46 (11)
N2—N1—C1—C11	177.48 (9)	C11—C12—C13—C14	0.64 (19)
N1—N2—C2—C3	−2.20 (17)	C12—C13—C14—C15	−1.1 (2)
N1—N2—C2—C4	−179.97 (10)	C13—C14—C15—C16	0.1 (2)
O1—C1—C11—C12	−142.74 (12)	C14—C15—C16—C11	1.4 (2)
N1—C1—C11—C12	34.93 (15)	C12—C11—C16—C15	−1.89 (18)
O1—C1—C11—C16	32.94 (16)	C1—C11—C16—C15	−177.74 (11)
N1—C1—C11—C16	−149.38 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.868 (16)	2.235 (16)	3.0912 (14)	169.0 (12)
N1—H1···N2^i	0.868 (16)	2.611 (15)	3.1826 (14)	124.4 (11)
C3—H3C···O1^i	0.98	2.37	3.1238 (17)	133

Symmetry code: (i) x, −y+3/2, z+1/2.

(II) 1-Benzoyl-2-(1-cyclohexylethylidene)hydrazone

Crystal data

C15H20N2O	Z = 4
Mr = 244.33	F(000) = 528
Monoclinic, P21/c	Dx = 1.202 Mg m^−3
a = 9.3086 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 18.283 (2) Å	µ = 0.08 mm^−1
c = 8.1543 (7) Å	T = 173 K
β = 103.328 (7)°	Block, colourless
V = 1350.4 (2) Å^3	0.54 × 0.36 × 0.24 mm

Data collection

Stoe IPDS II two-circle diffractometer	1909 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.105
Graphite monochromator	θmax = 25.9°, θmin = 3.2°
φ scans	h = −11→11
18518 measured reflections	k = −22→22
2589 independent reflections	l = −9→9

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ^2(Fo^2) + (0.067P)^2] where P = (Fo^2 + 2Fc^2)/3
2589 reflections	(Δ/σ)max < 0.001
168 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.13515 (12)	0.16917 (5)	0.46486 (12)	0.0418 (3)
N1	0.08197 (12)	0.26595 (6)	0.61526 (14)	0.0328 (3)
H1	0.0817 (16)	0.2824 (8)	0.712 (2)	0.036 (4)*
N2	−0.01675 (12)	0.29356 (6)	0.47372 (13)	0.0347 (3)
C1	0.15294 (14)	0.20326 (7)	0.59794 (16)	0.0326 (3)
C2	−0.10240 (15)	0.34517 (8)	0.49664 (17)	0.0358 (3)
C3	−0.10804 (19)	0.37784 (9)	0.66290 (18)	0.0484 (4)
H3A	−0.1211	0.3389	0.7408	0.073*
H3B	−0.1911	0.4121	0.6478	0.073*
H3C	−0.0157	0.4040	0.7092	0.073*
C11	0.25713 (14)	0.17564 (7)	0.75383 (16)	0.0317 (3)
C12	0.34857 (15)	0.22194 (8)	0.86722 (16)	0.0348 (3)
H12	0.3468	0.2731	0.8472	0.042*
C13	0.44224 (15)	0.19306 (9)	1.00958 (17)	0.0403 (3)
H13	0.5055	0.2246	1.0866	0.048*
C14	0.44405 (16)	0.11902 (9)	1.04003 (19)	0.0440 (4)
H14	0.5062	0.0997	1.1397	0.053*
C15	0.35541 (17)	0.07253 (8)	0.9257 (2)	0.0454 (4)
H15	0.3577	0.0213	0.9458	0.055*
C16	0.26328 (16)	0.10108 (8)	0.78181 (18)	0.0388 (3)
H16	0.2040	0.0692	0.7020	0.047*
C21	−0.20740 (15)	0.37763 (8)	0.34427 (17)	0.0376 (3)
H21	−0.3057	0.3827	0.3730	0.045*
C22	−0.22981 (19)	0.33092 (8)	0.18650 (19)	0.0458 (4)
H22A	−0.2654	0.2818	0.2097	0.055*
H22B	−0.1345	0.3249	0.1537	0.055*
C23	−0.34218 (19)	0.36667 (9)	0.0418 (2)	0.0510 (4)
H23A	−0.3527	0.3365	−0.0612	0.061*
H23B	−0.4396	0.3688	0.0710	0.061*
C24	−0.2944 (2)	0.44324 (10)	0.00727 (19)	0.0521 (4)
H24A	−0.2022	0.4405	−0.0335	0.063*
H24B	−0.3714	0.4659	−0.0826	0.063*
C25	−0.2688 (2)	0.49043 (9)	0.1627 (2)	0.0504 (4)
H25A	−0.3634	0.4979	0.1962	0.060*
H25B	−0.2314	0.5389	0.1376	0.060*
C26	−0.15720 (17)	0.45463 (8)	0.30795 (18)	0.0429 (4)
H26A	−0.1460	0.4852	0.4104	0.051*
H26B	−0.0599	0.4517	0.2787	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0525 (6)	0.0415 (6)	0.0272 (5)	0.0010 (5)	0.0004 (4)	−0.0049 (4)
N1	0.0361 (6)	0.0387 (6)	0.0206 (6)	0.0028 (5)	0.0004 (4)	0.0009 (5)
N2	0.0372 (6)	0.0397 (6)	0.0235 (5)	−0.0010 (5)	−0.0005 (4)	0.0049 (5)
C1	0.0337 (6)	0.0367 (7)	0.0255 (6)	−0.0043 (5)	0.0028 (5)	0.0003 (5)
C2	0.0361 (7)	0.0365 (7)	0.0317 (7)	−0.0016 (6)	0.0013 (5)	0.0033 (5)
C3	0.0554 (9)	0.0524 (9)	0.0337 (7)	0.0151 (7)	0.0028 (7)	0.0014 (7)
C11	0.0305 (6)	0.0380 (7)	0.0260 (6)	0.0012 (5)	0.0050 (5)	0.0003 (5)
C12	0.0366 (7)	0.0359 (7)	0.0306 (7)	−0.0008 (6)	0.0051 (5)	−0.0008 (5)
C13	0.0360 (7)	0.0507 (8)	0.0311 (7)	−0.0017 (6)	0.0010 (6)	−0.0030 (6)
C14	0.0373 (7)	0.0556 (9)	0.0356 (7)	0.0057 (7)	0.0015 (6)	0.0108 (6)
C15	0.0449 (8)	0.0395 (8)	0.0490 (9)	0.0031 (6)	0.0048 (7)	0.0097 (6)
C16	0.0373 (7)	0.0383 (7)	0.0381 (7)	−0.0014 (6)	0.0031 (6)	−0.0009 (6)
C21	0.0354 (7)	0.0428 (8)	0.0311 (7)	0.0024 (6)	0.0006 (6)	0.0032 (6)
C22	0.0510 (9)	0.0414 (8)	0.0371 (8)	0.0028 (7)	−0.0058 (7)	0.0002 (6)
C23	0.0552 (9)	0.0502 (9)	0.0366 (8)	−0.0002 (7)	−0.0121 (7)	0.0006 (7)
C24	0.0583 (10)	0.0576 (10)	0.0330 (8)	0.0019 (8)	−0.0046 (7)	0.0096 (7)
C25	0.0586 (10)	0.0425 (8)	0.0439 (8)	0.0046 (7)	−0.0007 (7)	0.0071 (7)
C26	0.0485 (8)	0.0399 (8)	0.0347 (7)	0.0008 (7)	−0.0018 (6)	0.0005 (6)

Geometric parameters (Å, º)

O1—C1	1.2290 (16)	C15—H15	0.9500
N1—C1	1.3464 (18)	C16—H16	0.9500
N1—N2	1.3937 (15)	C21—C22	1.518 (2)
N1—H1	0.847 (17)	C21—C26	1.533 (2)
N2—C2	1.2767 (19)	C21—H21	1.0000
C1—C11	1.4977 (18)	C22—C23	1.531 (2)
C2—C3	1.493 (2)	C22—H22A	0.9900
C2—C21	1.5137 (18)	C22—H22B	0.9900
C3—H3A	0.9800	C23—C24	1.515 (2)
C3—H3B	0.9800	C23—H23A	0.9900
C3—H3C	0.9800	C23—H23B	0.9900
C11—C16	1.381 (2)	C24—C25	1.506 (2)
C11—C12	1.3902 (19)	C24—H24A	0.9900
C12—C13	1.386 (2)	C24—H24B	0.9900
C12—H12	0.9500	C25—C26	1.531 (2)
C13—C14	1.376 (2)	C25—H25A	0.9900
C13—H13	0.9500	C25—H25B	0.9900
C14—C15	1.385 (2)	C26—H26A	0.9900
C14—H14	0.9500	C26—H26B	0.9900
C15—C16	1.386 (2)
C1—N1—N2	117.85 (11)	C2—C21—C26	110.52 (11)
C1—N1—H1	120.4 (10)	C22—C21—C26	109.96 (12)
N2—N1—H1	120.1 (10)	C2—C21—H21	107.2
C2—N2—N1	117.47 (11)	C22—C21—H21	107.2
O1—C1—N1	123.70 (12)	C26—C21—H21	107.2
O1—C1—C11	120.50 (12)	C21—C22—C23	110.43 (12)
N1—C1—C11	115.81 (11)	C21—C22—H22A	109.6
N2—C2—C3	125.62 (12)	C23—C22—H22A	109.6
N2—C2—C21	118.46 (12)	C21—C22—H22B	109.6
C3—C2—C21	115.92 (12)	C23—C22—H22B	109.6
C2—C3—H3A	109.5	H22A—C22—H22B	108.1
C2—C3—H3B	109.5	C24—C23—C22	111.09 (13)
H3A—C3—H3B	109.5	C24—C23—H23A	109.4
C2—C3—H3C	109.5	C22—C23—H23A	109.4
H3A—C3—H3C	109.5	C24—C23—H23B	109.4
H3B—C3—H3C	109.5	C22—C23—H23B	109.4
C16—C11—C12	119.69 (12)	H23A—C23—H23B	108.0
C16—C11—C1	117.84 (12)	C25—C24—C23	111.68 (13)
C12—C11—C1	122.45 (12)	C25—C24—H24A	109.3
C13—C12—C11	119.72 (13)	C23—C24—H24A	109.3
C13—C12—H12	120.1	C25—C24—H24B	109.3
C11—C12—H12	120.1	C23—C24—H24B	109.3
C14—C13—C12	120.35 (13)	H24A—C24—H24B	107.9
C14—C13—H13	119.8	C24—C25—C26	110.71 (13)
C12—C13—H13	119.8	C24—C25—H25A	109.5
C13—C14—C15	120.12 (13)	C26—C25—H25A	109.5
C13—C14—H14	119.9	C24—C25—H25B	109.5
C15—C14—H14	119.9	C26—C25—H25B	109.5
C14—C15—C16	119.68 (14)	H25A—C25—H25B	108.1
C14—C15—H15	120.2	C25—C26—C21	111.05 (12)
C16—C15—H15	120.2	C25—C26—H26A	109.4
C11—C16—C15	120.37 (14)	C21—C26—H26A	109.4
C11—C16—H16	119.8	C25—C26—H26B	109.4
C15—C16—H16	119.8	C21—C26—H26B	109.4
C2—C21—C22	114.31 (12)	H26A—C26—H26B	108.0
C1—N1—N2—C2	167.93 (12)	C1—C11—C16—C15	−178.66 (13)
N2—N1—C1—O1	−0.2 (2)	C14—C15—C16—C11	−1.4 (2)
N2—N1—C1—C11	−179.67 (11)	N2—C2—C21—C22	16.6 (2)
N1—N2—C2—C3	−1.2 (2)	C3—C2—C21—C22	−163.95 (14)
N1—N2—C2—C21	178.18 (11)	N2—C2—C21—C26	−108.03 (15)
O1—C1—C11—C16	−38.09 (18)	C3—C2—C21—C26	71.37 (17)
N1—C1—C11—C16	141.40 (13)	C2—C21—C22—C23	177.68 (13)
O1—C1—C11—C12	140.47 (14)	C26—C21—C22—C23	−57.34 (17)
N1—C1—C11—C12	−40.04 (18)	C21—C22—C23—C24	56.94 (19)
C16—C11—C12—C13	−1.7 (2)	C22—C23—C24—C25	−56.1 (2)
C1—C11—C12—C13	179.77 (12)	C23—C24—C25—C26	55.42 (19)
C11—C12—C13—C14	−0.7 (2)	C24—C25—C26—C21	−56.13 (19)
C12—C13—C14—C15	2.0 (2)	C2—C21—C26—C25	−175.59 (13)
C13—C14—C15—C16	−1.0 (2)	C22—C21—C26—C25	57.28 (17)
C12—C11—C16—C15	2.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.847 (17)	2.191 (18)	3.0213 (16)	166.6 (14)
C3—H3C···O1^i	0.98	2.60	3.0589 (18)	109

Symmetry code: (i) x, −y+1/2, z+1/2.

(III) 1-Benzoyl-2-[1-(naphthalen-2-yl)ethylidene]hydrazone

Crystal data

C19H16N2O	Z = 4
Mr = 288.34	F(000) = 608
Monoclinic, P21/n	Dx = 1.348 Mg m^−3
a = 5.5789 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.6868 (9) Å	µ = 0.09 mm^−1
c = 33.128 (3) Å	T = 173 K
β = 90.356 (7)°	Block, colourless
V = 1420.6 (2) Å^3	0.53 × 0.26 × 0.21 mm

Data collection

Stoe IPDS II two-circle diffractometer	1715 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.061
Graphite monochromator	θmax = 25.9°, θmin = 2.5°
φ scans	h = −6→6
19261 measured reflections	k = −9→9
2754 independent reflections	l = −40→40

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 0.85	w = 1/[σ^2(Fo^2) + (0.044P)^2] where P = (Fo^2 + 2Fc^2)/3
2754 reflections	(Δ/σ)max < 0.001
204 parameters	Δρmax = 0.11 e Å^−3
0 restraints	Δρmin = −0.14 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.56121 (19)	0.65071 (15)	0.12680 (3)	0.0530 (3)
N1	0.9449 (2)	0.69057 (16)	0.10642 (3)	0.0424 (3)
H1	1.098 (3)	0.697 (2)	0.1131 (5)	0.059 (5)*
N2	0.8799 (2)	0.69289 (15)	0.06596 (3)	0.0415 (3)
C1	0.7759 (3)	0.66225 (19)	0.13468 (4)	0.0421 (3)
C2	1.0365 (3)	0.75648 (18)	0.04154 (4)	0.0391 (3)
C3	1.2686 (3)	0.8376 (2)	0.05458 (4)	0.0458 (4)
H3A	1.2479	0.8935	0.0809	0.069*
H3B	1.3172	0.9249	0.0347	0.069*
H3C	1.3923	0.7475	0.0567	0.069*
C11	0.8672 (3)	0.64625 (19)	0.17717 (4)	0.0400 (3)
C12	1.0829 (3)	0.7171 (2)	0.19055 (4)	0.0455 (4)
H12	1.1814	0.7798	0.1723	0.055*
C13	1.1546 (3)	0.6965 (2)	0.23041 (4)	0.0485 (4)
H13	1.3014	0.7460	0.2395	0.058*
C14	1.0138 (3)	0.6046 (2)	0.25695 (4)	0.0485 (4)
H14	1.0642	0.5898	0.2842	0.058*
C15	0.7991 (3)	0.5337 (2)	0.24390 (4)	0.0495 (4)
H15	0.7016	0.4704	0.2621	0.059*
C16	0.7270 (3)	0.5553 (2)	0.20436 (4)	0.0452 (4)
H16	0.5788	0.5070	0.1956	0.054*
C21	0.9744 (3)	0.74471 (17)	−0.00194 (4)	0.0376 (3)
C22	0.7602 (2)	0.65897 (18)	−0.01471 (4)	0.0408 (3)
H22	0.6570	0.6102	0.0050	0.049*
C23	0.7003 (3)	0.64553 (19)	−0.05435 (4)	0.0423 (3)
H23	0.5563	0.5876	−0.0618	0.051*
C24	0.8487 (3)	0.71636 (18)	−0.08483 (4)	0.0401 (3)
C25	0.7932 (3)	0.70564 (19)	−0.12645 (4)	0.0474 (4)
H25	0.6506	0.6485	−0.1350	0.057*
C26	0.9418 (3)	0.7763 (2)	−0.15444 (4)	0.0521 (4)
H26	0.9030	0.7670	−0.1823	0.062*
C27	1.1520 (3)	0.8628 (2)	−0.14244 (4)	0.0528 (4)
H27	1.2536	0.9130	−0.1622	0.063*
C28	1.2110 (3)	0.8753 (2)	−0.10260 (4)	0.0479 (4)
H28	1.3534	0.9344	−0.0948	0.057*
C29	1.0633 (3)	0.80149 (18)	−0.07271 (4)	0.0404 (3)
C30	1.1204 (3)	0.81296 (18)	−0.03115 (4)	0.0405 (3)
H30	1.2644	0.8697	−0.0232	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0455 (6)	0.0726 (7)	0.0410 (5)	−0.0031 (6)	−0.0029 (5)	0.0047 (5)
N1	0.0449 (8)	0.0506 (8)	0.0315 (6)	0.0012 (6)	−0.0012 (5)	−0.0003 (5)
N2	0.0479 (7)	0.0443 (7)	0.0323 (6)	0.0038 (6)	−0.0003 (5)	0.0004 (5)
C1	0.0469 (9)	0.0421 (8)	0.0372 (7)	0.0017 (7)	0.0005 (6)	−0.0015 (6)
C2	0.0411 (8)	0.0382 (8)	0.0379 (7)	0.0061 (6)	−0.0012 (6)	−0.0006 (6)
C3	0.0450 (9)	0.0541 (9)	0.0382 (7)	0.0010 (7)	−0.0034 (6)	0.0005 (6)
C11	0.0442 (8)	0.0417 (8)	0.0342 (7)	0.0037 (7)	0.0019 (6)	−0.0017 (6)
C12	0.0463 (9)	0.0518 (9)	0.0385 (8)	−0.0027 (7)	0.0045 (6)	−0.0019 (6)
C13	0.0436 (9)	0.0603 (10)	0.0416 (8)	−0.0013 (7)	−0.0006 (7)	−0.0050 (7)
C14	0.0524 (10)	0.0587 (10)	0.0344 (7)	0.0034 (8)	−0.0033 (7)	0.0003 (7)
C15	0.0549 (10)	0.0575 (10)	0.0362 (8)	−0.0052 (8)	0.0033 (7)	0.0037 (7)
C16	0.0446 (9)	0.0527 (9)	0.0383 (8)	−0.0039 (7)	0.0006 (6)	−0.0017 (6)
C21	0.0394 (8)	0.0375 (8)	0.0361 (7)	0.0062 (6)	0.0002 (6)	−0.0003 (6)
C22	0.0424 (8)	0.0406 (8)	0.0393 (7)	0.0012 (7)	0.0019 (6)	0.0000 (6)
C23	0.0428 (8)	0.0416 (8)	0.0423 (8)	0.0004 (7)	−0.0028 (6)	−0.0008 (6)
C24	0.0424 (8)	0.0397 (8)	0.0381 (7)	0.0072 (6)	−0.0020 (6)	−0.0027 (6)
C25	0.0523 (9)	0.0507 (9)	0.0389 (8)	0.0066 (7)	−0.0055 (7)	−0.0031 (7)
C26	0.0602 (10)	0.0627 (10)	0.0334 (7)	0.0135 (8)	−0.0029 (7)	0.0011 (7)
C27	0.0535 (10)	0.0647 (10)	0.0402 (8)	0.0095 (8)	0.0064 (7)	0.0071 (7)
C28	0.0441 (8)	0.0584 (10)	0.0411 (8)	0.0010 (8)	0.0029 (6)	0.0043 (7)
C29	0.0418 (8)	0.0427 (8)	0.0368 (7)	0.0072 (7)	0.0005 (6)	0.0005 (6)
C30	0.0386 (8)	0.0436 (8)	0.0393 (7)	0.0018 (7)	−0.0021 (6)	−0.0009 (6)

Geometric parameters (Å, º)

O1—C1	1.2273 (17)	C15—H15	0.9500
N1—C1	1.3507 (18)	C16—H16	0.9500
N1—N2	1.3864 (16)	C21—C30	1.3730 (19)
N1—H1	0.885 (17)	C21—C22	1.427 (2)
N2—C2	1.2907 (17)	C22—C23	1.3569 (19)
C1—C11	1.4988 (19)	C22—H22	0.9500
C2—C21	1.4820 (19)	C23—C24	1.4184 (19)
C2—C3	1.498 (2)	C23—H23	0.9500
C3—H3A	0.9800	C24—C25	1.414 (2)
C3—H3B	0.9800	C24—C29	1.420 (2)
C3—H3C	0.9800	C25—C26	1.361 (2)
C11—C16	1.3860 (19)	C25—H25	0.9500
C11—C12	1.391 (2)	C26—C27	1.404 (2)
C12—C13	1.387 (2)	C26—H26	0.9500
C12—H12	0.9500	C27—C28	1.362 (2)
C13—C14	1.378 (2)	C27—H27	0.9500
C13—H13	0.9500	C28—C29	1.411 (2)
C14—C15	1.383 (2)	C28—H28	0.9500
C14—H14	0.9500	C29—C30	1.4140 (19)
C15—C16	1.378 (2)	C30—H30	0.9500
C1—N1—N2	119.52 (13)	C15—C16—H16	119.5
C1—N1—H1	121.0 (11)	C11—C16—H16	119.5
N2—N1—H1	119.2 (11)	C30—C21—C22	117.84 (13)
C2—N2—N1	115.90 (12)	C30—C21—C2	121.71 (13)
O1—C1—N1	123.27 (13)	C22—C21—C2	120.45 (12)
O1—C1—C11	121.29 (13)	C23—C22—C21	121.54 (13)
N1—C1—C11	115.44 (13)	C23—C22—H22	119.2
N2—C2—C21	115.53 (13)	C21—C22—H22	119.2
N2—C2—C3	124.33 (12)	C22—C23—C24	121.21 (14)
C21—C2—C3	120.14 (12)	C22—C23—H23	119.4
C2—C3—H3A	109.5	C24—C23—H23	119.4
C2—C3—H3B	109.5	C25—C24—C23	123.14 (14)
H3A—C3—H3B	109.5	C25—C24—C29	118.79 (13)
C2—C3—H3C	109.5	C23—C24—C29	118.07 (12)
H3A—C3—H3C	109.5	C26—C25—C24	120.71 (15)
H3B—C3—H3C	109.5	C26—C25—H25	119.6
C16—C11—C12	118.76 (13)	C24—C25—H25	119.6
C16—C11—C1	117.50 (13)	C25—C26—C27	120.51 (14)
C12—C11—C1	123.74 (13)	C25—C26—H26	119.7
C13—C12—C11	120.18 (14)	C27—C26—H26	119.7
C13—C12—H12	119.9	C28—C27—C26	120.27 (15)
C11—C12—H12	119.9	C28—C27—H27	119.9
C14—C13—C12	120.26 (15)	C26—C27—H27	119.9
C14—C13—H13	119.9	C27—C28—C29	120.90 (15)
C12—C13—H13	119.9	C27—C28—H28	119.6
C13—C14—C15	119.92 (13)	C29—C28—H28	119.6
C13—C14—H14	120.0	C28—C29—C30	121.95 (14)
C15—C14—H14	120.0	C28—C29—C24	118.80 (13)
C16—C15—C14	119.81 (14)	C30—C29—C24	119.23 (13)
C16—C15—H15	120.1	C21—C30—C29	122.10 (14)
C14—C15—H15	120.1	C21—C30—H30	118.9
C15—C16—C11	121.06 (14)	C29—C30—H30	118.9
C1—N1—N2—C2	165.74 (13)	C30—C21—C22—C23	−0.4 (2)
N2—N1—C1—O1	−5.6 (2)	C2—C21—C22—C23	−179.56 (13)
N2—N1—C1—C11	174.73 (12)	C21—C22—C23—C24	0.0 (2)
N1—N2—C2—C21	174.98 (12)	C22—C23—C24—C25	−179.91 (14)
N1—N2—C2—C3	−4.82 (19)	C22—C23—C24—C29	0.3 (2)
O1—C1—C11—C16	24.1 (2)	C23—C24—C25—C26	179.85 (14)
N1—C1—C11—C16	−156.18 (13)	C29—C24—C25—C26	−0.3 (2)
O1—C1—C11—C12	−155.91 (15)	C24—C25—C26—C27	−0.7 (2)
N1—C1—C11—C12	23.8 (2)	C25—C26—C27—C28	0.8 (2)
C16—C11—C12—C13	−0.1 (2)	C26—C27—C28—C29	0.2 (2)
C1—C11—C12—C13	179.97 (14)	C27—C28—C29—C30	−179.87 (15)
C11—C12—C13—C14	0.5 (2)	C27—C28—C29—C24	−1.2 (2)
C12—C13—C14—C15	−0.6 (2)	C25—C24—C29—C28	1.24 (19)
C13—C14—C15—C16	0.1 (2)	C23—C24—C29—C28	−178.94 (13)
C14—C15—C16—C11	0.4 (2)	C25—C24—C29—C30	179.98 (13)
C12—C11—C16—C15	−0.4 (2)	C23—C24—C29—C30	−0.19 (19)
C1—C11—C16—C15	179.55 (14)	C22—C21—C30—C29	0.5 (2)
N2—C2—C21—C30	177.53 (13)	C2—C21—C30—C29	179.63 (13)
C3—C2—C21—C30	−2.7 (2)	C28—C29—C30—C21	178.51 (14)
N2—C2—C21—C22	−3.33 (19)	C24—C29—C30—C21	−0.2 (2)
C3—C2—C21—C22	176.47 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.885 (17)	2.643 (18)	3.5134 (18)	168.1 (15)
C3—H3C···O1^i	0.98	2.61	3.2256 (18)	121
C25—H25···O1^ii	0.95	2.60	3.378 (2)	139

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z.

(IV) 1-Benzoyl-2-(1-cyclohexylbenzylidene)hydrazone

Crystal data

C20H22N2O	Z = 8
Mr = 306.40	F(000) = 1312
Monoclinic, C2/c	Dx = 1.211 Mg m^−3
a = 16.0939 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.8666 (8) Å	µ = 0.08 mm^−1
c = 16.8556 (16) Å	T = 173 K
β = 116.661 (7)°	Block, colourless
V = 3361.7 (5) Å^3	0.54 × 0.52 × 0.50 mm

Data collection

Stoe IPDS II two-circle diffractometer	3004 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.069
Graphite monochromator	θmax = 27.9°, θmin = 3.9°
φ scans	h = −21→20
27068 measured reflections	k = −18→18
3956 independent reflections	l = −21→22

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.055P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
3956 reflections	Δρmax = 0.27 e Å^−3
213 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0023 (4)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.24605 (5)	0.67792 (5)	0.19028 (5)	0.03552 (18)
N1	0.35016 (7)	0.67643 (6)	0.13423 (7)	0.0355 (2)
H1	0.3861 (10)	0.6413 (11)	0.1180 (10)	0.048 (4)*
N2	0.34463 (6)	0.77523 (6)	0.11967 (6)	0.0324 (2)
C1	0.29883 (7)	0.63355 (7)	0.16982 (6)	0.0280 (2)
C2	0.39419 (7)	0.80748 (7)	0.08319 (7)	0.0293 (2)
C11	0.31176 (7)	0.52677 (7)	0.18315 (6)	0.0280 (2)
C12	0.37577 (8)	0.47322 (7)	0.16725 (8)	0.0361 (2)
H12	0.4157	0.5045	0.1476	0.043*
C13	0.38133 (9)	0.37404 (8)	0.18013 (8)	0.0410 (3)
H13	0.4241	0.3374	0.1679	0.049*
C14	0.32513 (8)	0.32849 (8)	0.21056 (8)	0.0393 (3)
H14	0.3292	0.2606	0.2191	0.047*
C15	0.26294 (8)	0.38124 (8)	0.22867 (8)	0.0399 (3)
H15	0.2252	0.3500	0.2509	0.048*
C16	0.25572 (8)	0.47997 (7)	0.21436 (7)	0.0348 (2)
H16	0.2121	0.5160	0.2259	0.042*
C21	0.45368 (7)	0.74368 (7)	0.05807 (7)	0.0289 (2)
C22	0.54414 (8)	0.72163 (8)	0.11993 (7)	0.0365 (2)
H22	0.5690	0.7493	0.1776	0.044*
C23	0.59806 (8)	0.65961 (9)	0.09792 (8)	0.0404 (3)
H23	0.6602	0.6458	0.1400	0.048*
C24	0.56153 (9)	0.61783 (9)	0.01477 (8)	0.0408 (3)
H24	0.5982	0.5746	0.0000	0.049*
C25	0.47170 (8)	0.63889 (9)	−0.04693 (8)	0.0412 (3)
H25	0.4468	0.6101	−0.1041	0.049*
C26	0.41769 (8)	0.70182 (8)	−0.02588 (7)	0.0351 (2)
H26	0.3561	0.7164	−0.0687	0.042*
C31	0.39266 (7)	0.91430 (7)	0.06529 (7)	0.0292 (2)
H31	0.3777	0.9220	0.0013	0.035*
C32	0.31905 (8)	0.96972 (8)	0.08020 (8)	0.0379 (2)
H32A	0.3311	0.9630	0.1429	0.045*
H32B	0.2569	0.9422	0.0423	0.045*
C33	0.31997 (9)	1.07659 (8)	0.05806 (9)	0.0429 (3)
H33A	0.3028	1.0835	−0.0059	0.051*
H33B	0.2731	1.1114	0.0701	0.051*
C34	0.41514 (9)	1.12120 (8)	0.11249 (9)	0.0427 (3)
H34A	0.4145	1.1892	0.0942	0.051*
H34B	0.4295	1.1206	0.1761	0.051*
C35	0.49010 (9)	1.06638 (8)	0.10004 (9)	0.0425 (3)
H35A	0.5517	1.0938	0.1398	0.051*
H35B	0.4803	1.0743	0.0381	0.051*
C36	0.48926 (8)	0.95898 (8)	0.12024 (7)	0.0345 (2)
H36A	0.5073	0.9505	0.1842	0.041*
H36B	0.5355	0.9249	0.1068	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0402 (4)	0.0283 (3)	0.0471 (4)	0.0040 (3)	0.0276 (4)	0.0015 (3)
N1	0.0446 (5)	0.0232 (4)	0.0513 (6)	0.0021 (4)	0.0328 (5)	0.0019 (4)
N2	0.0377 (5)	0.0230 (4)	0.0424 (5)	0.0008 (3)	0.0233 (4)	0.0023 (3)
C1	0.0291 (5)	0.0257 (4)	0.0301 (5)	−0.0007 (4)	0.0141 (4)	−0.0009 (4)
C2	0.0296 (5)	0.0271 (5)	0.0322 (5)	0.0004 (4)	0.0147 (4)	0.0011 (4)
C11	0.0287 (5)	0.0253 (5)	0.0298 (5)	−0.0016 (3)	0.0129 (4)	−0.0008 (3)
C12	0.0435 (6)	0.0289 (5)	0.0469 (6)	−0.0004 (4)	0.0300 (5)	−0.0005 (4)
C13	0.0490 (7)	0.0296 (5)	0.0536 (7)	0.0046 (5)	0.0312 (6)	−0.0009 (5)
C14	0.0458 (6)	0.0251 (5)	0.0482 (6)	−0.0006 (4)	0.0221 (5)	0.0016 (4)
C15	0.0404 (6)	0.0320 (5)	0.0522 (6)	−0.0031 (4)	0.0252 (5)	0.0063 (5)
C16	0.0334 (6)	0.0304 (5)	0.0458 (6)	0.0007 (4)	0.0224 (5)	0.0030 (4)
C21	0.0317 (5)	0.0250 (4)	0.0343 (5)	0.0007 (4)	0.0187 (4)	0.0038 (4)
C22	0.0361 (6)	0.0397 (6)	0.0325 (5)	0.0042 (4)	0.0145 (4)	0.0005 (4)
C23	0.0334 (6)	0.0466 (6)	0.0392 (6)	0.0107 (5)	0.0146 (5)	0.0032 (5)
C24	0.0427 (6)	0.0422 (6)	0.0447 (6)	0.0094 (5)	0.0259 (5)	0.0000 (5)
C25	0.0426 (6)	0.0449 (6)	0.0370 (6)	0.0030 (5)	0.0188 (5)	−0.0065 (5)
C26	0.0325 (5)	0.0362 (5)	0.0360 (5)	0.0027 (4)	0.0148 (4)	0.0003 (4)
C31	0.0328 (5)	0.0246 (4)	0.0339 (5)	0.0011 (4)	0.0182 (4)	0.0021 (4)
C32	0.0345 (6)	0.0290 (5)	0.0550 (7)	0.0017 (4)	0.0245 (5)	0.0006 (4)
C33	0.0400 (6)	0.0281 (5)	0.0620 (7)	0.0052 (4)	0.0241 (5)	0.0001 (5)
C34	0.0475 (7)	0.0290 (5)	0.0555 (7)	−0.0008 (5)	0.0268 (6)	−0.0068 (5)
C35	0.0417 (6)	0.0300 (5)	0.0618 (7)	−0.0058 (4)	0.0285 (6)	−0.0044 (5)
C36	0.0324 (5)	0.0308 (5)	0.0428 (6)	−0.0002 (4)	0.0189 (4)	−0.0014 (4)

Geometric parameters (Å, º)

O1—C1	1.2174 (12)	C23—H23	0.9500
N1—C1	1.3567 (13)	C24—C25	1.3812 (17)
N1—N2	1.3876 (11)	C24—H24	0.9500
N1—H1	0.887 (15)	C25—C26	1.3854 (16)
N2—C2	1.2864 (13)	C25—H25	0.9500
C1—C11	1.4980 (13)	C26—H26	0.9500
C2—C21	1.4975 (14)	C31—C32	1.5246 (14)
C2—C31	1.5097 (13)	C31—C36	1.5382 (15)
C11—C12	1.3900 (14)	C31—H31	1.0000
C11—C16	1.3919 (14)	C32—C33	1.5298 (15)
C12—C13	1.3889 (15)	C32—H32A	0.9900
C12—H12	0.9500	C32—H32B	0.9900
C13—C14	1.3770 (17)	C33—C34	1.5197 (17)
C13—H13	0.9500	C33—H33A	0.9900
C14—C15	1.3801 (17)	C33—H33B	0.9900
C14—H14	0.9500	C34—C35	1.5181 (17)
C15—C16	1.3858 (15)	C34—H34A	0.9900
C15—H15	0.9500	C34—H34B	0.9900
C16—H16	0.9500	C35—C36	1.5291 (15)
C21—C22	1.3921 (15)	C35—H35A	0.9900
C21—C26	1.3925 (15)	C35—H35B	0.9900
C22—C23	1.3854 (16)	C36—H36A	0.9900
C22—H22	0.9500	C36—H36B	0.9900
C23—C24	1.3806 (17)
C1—N1—N2	120.49 (9)	C24—C25—H25	119.8
C1—N1—H1	120.4 (9)	C26—C25—H25	119.8
N2—N1—H1	119.1 (9)	C25—C26—C21	120.00 (10)
C2—N2—N1	115.05 (9)	C25—C26—H26	120.0
O1—C1—N1	122.98 (9)	C21—C26—H26	120.0
O1—C1—C11	121.65 (9)	C2—C31—C32	113.94 (9)
N1—C1—C11	115.36 (8)	C2—C31—C36	110.69 (8)
N2—C2—C21	122.83 (9)	C32—C31—C36	110.36 (8)
N2—C2—C31	118.60 (9)	C2—C31—H31	107.2
C21—C2—C31	118.57 (8)	C32—C31—H31	107.2
C12—C11—C16	119.06 (9)	C36—C31—H31	107.2
C12—C11—C1	124.35 (9)	C31—C32—C33	110.78 (9)
C16—C11—C1	116.59 (9)	C31—C32—H32A	109.5
C13—C12—C11	120.01 (10)	C33—C32—H32A	109.5
C13—C12—H12	120.0	C31—C32—H32B	109.5
C11—C12—H12	120.0	C33—C32—H32B	109.5
C14—C13—C12	120.36 (10)	H32A—C32—H32B	108.1
C14—C13—H13	119.8	C34—C33—C32	111.38 (10)
C12—C13—H13	119.8	C34—C33—H33A	109.4
C13—C14—C15	120.13 (10)	C32—C33—H33A	109.4
C13—C14—H14	119.9	C34—C33—H33B	109.4
C15—C14—H14	119.9	C32—C33—H33B	109.4
C14—C15—C16	119.84 (10)	H33A—C33—H33B	108.0
C14—C15—H15	120.1	C35—C34—C33	111.16 (10)
C16—C15—H15	120.1	C35—C34—H34A	109.4
C15—C16—C11	120.56 (10)	C33—C34—H34A	109.4
C15—C16—H16	119.7	C35—C34—H34B	109.4
C11—C16—H16	119.7	C33—C34—H34B	109.4
C22—C21—C26	119.20 (9)	H34A—C34—H34B	108.0
C22—C21—C2	120.29 (9)	C34—C35—C36	111.71 (10)
C26—C21—C2	120.43 (9)	C34—C35—H35A	109.3
C23—C22—C21	120.40 (10)	C36—C35—H35A	109.3
C23—C22—H22	119.8	C34—C35—H35B	109.3
C21—C22—H22	119.8	C36—C35—H35B	109.3
C24—C23—C22	119.98 (10)	H35A—C35—H35B	107.9
C24—C23—H23	120.0	C35—C36—C31	111.45 (9)
C22—C23—H23	120.0	C35—C36—H36A	109.3
C23—C24—C25	120.05 (10)	C31—C36—H36A	109.3
C23—C24—H24	120.0	C35—C36—H36B	109.3
C25—C24—H24	120.0	C31—C36—H36B	109.3
C24—C25—C26	120.36 (10)	H36A—C36—H36B	108.0
C1—N1—N2—C2	−177.97 (10)	C26—C21—C22—C23	0.71 (16)
N2—N1—C1—O1	0.25 (16)	C2—C21—C22—C23	177.47 (10)
N2—N1—C1—C11	−179.36 (9)	C21—C22—C23—C24	−1.25 (18)
N1—N2—C2—C21	−0.01 (14)	C22—C23—C24—C25	0.92 (19)
N1—N2—C2—C31	−179.73 (9)	C23—C24—C25—C26	−0.06 (19)
O1—C1—C11—C12	−175.09 (10)	C24—C25—C26—C21	−0.48 (18)
N1—C1—C11—C12	4.52 (14)	C22—C21—C26—C25	0.15 (16)
O1—C1—C11—C16	4.28 (14)	C2—C21—C26—C25	−176.60 (10)
N1—C1—C11—C16	−176.11 (9)	N2—C2—C31—C32	−9.16 (14)
C16—C11—C12—C13	1.80 (16)	C21—C2—C31—C32	171.11 (9)
C1—C11—C12—C13	−178.84 (10)	N2—C2—C31—C36	115.91 (11)
C11—C12—C13—C14	−1.46 (18)	C21—C2—C31—C36	−63.82 (12)
C12—C13—C14—C15	−0.15 (18)	C2—C31—C32—C33	−178.30 (9)
C13—C14—C15—C16	1.39 (18)	C36—C31—C32—C33	56.45 (12)
C14—C15—C16—C11	−1.03 (17)	C31—C32—C33—C34	−57.18 (14)
C12—C11—C16—C15	−0.57 (16)	C32—C33—C34—C35	55.83 (14)
C1—C11—C16—C15	−179.97 (10)	C33—C34—C35—C36	−54.53 (14)
N2—C2—C21—C22	−86.56 (13)	C34—C35—C36—C31	54.56 (13)
C31—C2—C21—C22	93.16 (12)	C2—C31—C36—C35	177.58 (9)
N2—C2—C21—C26	90.16 (13)	C32—C31—C36—C35	−55.34 (12)
C31—C2—C21—C26	−90.12 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1^i	0.95	2.60	3.1911 (14)	121
C15—H15···O1^i	0.95	2.54	3.1644 (13)	123
C26—H26···O1^ii	0.95	2.45	3.2940 (14)	147
C23—H23···O1^iii	0.95	2.60	3.3266 (15)	133

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1/2, −y+3/2, −z; (iii) −x+1, y, −z+1/2.

(V) 1-Benzoyl-2-(1-phenylbenzylidene)hydrazone

Crystal data

C20H16N2O	Z = 8
Mr = 300.35	F(000) = 1264
Monoclinic, P21/n	Dx = 1.273 Mg m^−3
a = 16.863 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1678 (8) Å	µ = 0.08 mm^−1
c = 18.694 (2) Å	T = 173 K
β = 102.079 (6)°	Block, colourless
V = 3134.3 (5) Å^3	0.40 × 0.40 × 0.30 mm

Data collection

Stoe IPDS II two-circle diffractometer	3934 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.104
Graphite monochromator	θmax = 25.9°, θmin = 3.7°
φ scans	h = −20→20
42459 measured reflections	k = −12→12
6006 independent reflections	l = −22→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.072	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	w = 1/[σ^2(Fo^2) + (0.030P)^2] where P = (Fo^2 + 2Fc^2)/3
6006 reflections	(Δ/σ)max = 0.001
423 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.62400 (6)	0.57831 (10)	0.11953 (6)	0.0469 (3)
N1	0.72692 (7)	0.71078 (11)	0.10099 (6)	0.0308 (2)
H1	0.7817 (10)	0.7148 (15)	0.1000 (8)	0.045 (4)*
N2	0.67358 (7)	0.80383 (11)	0.06448 (6)	0.0324 (2)
C1	0.69633 (8)	0.60124 (13)	0.12687 (7)	0.0314 (3)
C2	0.70490 (8)	0.91454 (13)	0.05148 (7)	0.0298 (3)
C11	0.75907 (8)	0.50953 (13)	0.16759 (7)	0.0307 (3)
C12	0.83620 (9)	0.54952 (15)	0.20251 (8)	0.0393 (3)
H12	0.8513	0.6393	0.2008	0.047*
C13	0.89093 (11)	0.45974 (17)	0.23958 (9)	0.0534 (4)
H13	0.9437	0.4879	0.2629	0.064*
C14	0.86975 (11)	0.32946 (17)	0.24310 (9)	0.0541 (4)
H14	0.9078	0.2680	0.2687	0.065*
C15	0.79323 (10)	0.28874 (15)	0.20939 (9)	0.0444 (4)
H15	0.7783	0.1991	0.2120	0.053*
C16	0.73808 (9)	0.37774 (13)	0.17174 (8)	0.0354 (3)
H16	0.6854	0.3489	0.1485	0.042*
C21	0.79116 (8)	0.95346 (13)	0.07642 (7)	0.0304 (3)
C22	0.83542 (9)	0.99480 (13)	0.02559 (8)	0.0371 (3)
H22	0.8105	0.9962	−0.0249	0.044*
C23	0.91505 (10)	1.03383 (15)	0.04767 (11)	0.0543 (5)
H23	0.9452	1.0596	0.0124	0.065*
C24	0.95072 (10)	1.03544 (17)	0.12084 (13)	0.0648 (6)
H24	1.0054	1.0632	0.1361	0.078*
C25	0.90739 (11)	0.99685 (16)	0.17224 (11)	0.0589 (5)
H25	0.9322	0.9990	0.2228	0.071*
C26	0.82782 (9)	0.95495 (14)	0.15028 (8)	0.0411 (3)
H26	0.7983	0.9273	0.1857	0.049*
C31	0.64826 (8)	1.01266 (13)	0.00989 (7)	0.0316 (3)
C32	0.58138 (8)	0.97448 (15)	−0.04322 (7)	0.0367 (3)
H32	0.5742	0.8847	−0.0571	0.044*
C33	0.52553 (9)	1.06753 (17)	−0.07563 (8)	0.0447 (4)
H33	0.4800	1.0411	−0.1119	0.054*
C34	0.53502 (9)	1.19852 (17)	−0.05601 (9)	0.0475 (4)
H34	0.4955	1.2613	−0.0775	0.057*
C35	0.60206 (9)	1.23718 (16)	−0.00519 (9)	0.0467 (4)
H35	0.6093	1.3274	0.0078	0.056*
C36	0.65916 (9)	1.14543 (14)	0.02721 (8)	0.0390 (3)
H36	0.7060	1.1733	0.0614	0.047*
O1'	0.90552 (6)	0.68520 (10)	0.08764 (5)	0.0353 (2)
N1'	0.88923 (7)	0.69785 (12)	−0.03585 (6)	0.0316 (2)
H1'	0.9113 (10)	0.7140 (15)	−0.0722 (9)	0.042 (4)*
N2'	0.80623 (6)	0.69018 (11)	−0.04685 (6)	0.0311 (2)
C1'	0.93512 (8)	0.68921 (13)	0.03332 (7)	0.0296 (3)
C2'	0.76632 (8)	0.70836 (13)	−0.11272 (7)	0.0289 (3)
C11'	1.02467 (8)	0.68440 (13)	0.03825 (7)	0.0297 (3)
C12'	1.05980 (8)	0.63562 (13)	−0.01757 (8)	0.0341 (3)
H12'	1.0263	0.6060	−0.0620	0.041*
C13'	1.14339 (9)	0.63025 (14)	−0.00857 (9)	0.0409 (3)
H13'	1.1671	0.5967	−0.0467	0.049*
C14'	1.19216 (9)	0.67368 (15)	0.05569 (9)	0.0437 (4)
H14'	1.2495	0.6697	0.0618	0.052*
C15'	1.15805 (9)	0.72292 (16)	0.11120 (8)	0.0439 (4)
H15'	1.1919	0.7538	0.1551	0.053*
C16'	1.07451 (9)	0.72726 (15)	0.10285 (8)	0.0379 (3)
H16'	1.0512	0.7597	0.1415	0.045*
C21'	0.80575 (8)	0.73981 (13)	−0.17535 (7)	0.0299 (3)
C22'	0.81780 (9)	0.86896 (15)	−0.19420 (8)	0.0386 (3)
H22'	0.8003	0.9390	−0.1676	0.046*
C23'	0.85550 (10)	0.89611 (17)	−0.25198 (8)	0.0473 (4)
H23'	0.8633	0.9848	−0.2649	0.057*
C24'	0.88139 (9)	0.79596 (19)	−0.29035 (8)	0.0501 (4)
H24'	0.9074	0.8153	−0.3295	0.060*
C25'	0.86975 (10)	0.66766 (19)	−0.27228 (9)	0.0534 (4)
H25'	0.8874	0.5982	−0.2992	0.064*
C26'	0.83210 (9)	0.63906 (16)	−0.21469 (8)	0.0424 (4)
H26'	0.8244	0.5501	−0.2022	0.051*
C31'	0.67719 (8)	0.69210 (13)	−0.12642 (7)	0.0305 (3)
C32'	0.64182 (9)	0.61621 (14)	−0.07915 (8)	0.0365 (3)
H32'	0.6751	0.5761	−0.0376	0.044*
C33'	0.55860 (9)	0.59899 (16)	−0.09240 (9)	0.0439 (4)
H33'	0.5350	0.5476	−0.0599	0.053*
C34'	0.50985 (9)	0.65653 (16)	−0.15287 (9)	0.0465 (4)
H34'	0.4528	0.6438	−0.1621	0.056*
C35'	0.54356 (9)	0.73232 (16)	−0.19987 (8)	0.0431 (4)
H35'	0.5097	0.7729	−0.2410	0.052*
C36'	0.62723 (8)	0.74946 (14)	−0.18711 (8)	0.0352 (3)
H36'	0.6504	0.8006	−0.2200	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0321 (6)	0.0400 (6)	0.0700 (7)	−0.0007 (4)	0.0140 (5)	0.0101 (5)
N1	0.0247 (6)	0.0331 (6)	0.0353 (6)	0.0022 (5)	0.0075 (5)	0.0047 (5)
N2	0.0287 (6)	0.0350 (6)	0.0340 (6)	0.0041 (5)	0.0078 (5)	0.0033 (5)
C1	0.0316 (8)	0.0304 (7)	0.0342 (7)	−0.0031 (6)	0.0116 (6)	−0.0027 (5)
C2	0.0312 (7)	0.0315 (7)	0.0287 (7)	0.0006 (6)	0.0106 (5)	0.0001 (5)
C11	0.0355 (7)	0.0323 (7)	0.0273 (6)	−0.0012 (6)	0.0134 (5)	0.0002 (5)
C12	0.0434 (8)	0.0404 (8)	0.0332 (7)	−0.0064 (7)	0.0055 (6)	0.0056 (6)
C13	0.0488 (9)	0.0575 (11)	0.0469 (9)	−0.0045 (8)	−0.0058 (7)	0.0169 (8)
C14	0.0543 (10)	0.0519 (11)	0.0530 (10)	0.0093 (8)	0.0041 (8)	0.0174 (8)
C15	0.0563 (10)	0.0325 (8)	0.0480 (9)	0.0041 (7)	0.0193 (8)	0.0057 (7)
C16	0.0390 (8)	0.0321 (8)	0.0386 (7)	−0.0011 (6)	0.0161 (6)	−0.0015 (6)
C21	0.0301 (7)	0.0251 (7)	0.0358 (7)	0.0051 (5)	0.0061 (6)	0.0027 (5)
C22	0.0354 (8)	0.0302 (7)	0.0474 (8)	0.0035 (6)	0.0127 (6)	0.0059 (6)
C23	0.0366 (8)	0.0353 (9)	0.0951 (14)	0.0022 (7)	0.0228 (9)	0.0132 (9)
C24	0.0318 (9)	0.0389 (10)	0.1135 (17)	−0.0035 (7)	−0.0079 (10)	0.0097 (10)
C25	0.0572 (11)	0.0372 (9)	0.0668 (11)	0.0038 (8)	−0.0228 (9)	0.0034 (8)
C26	0.0471 (9)	0.0324 (8)	0.0398 (8)	0.0042 (6)	−0.0003 (7)	0.0040 (6)
C31	0.0290 (7)	0.0374 (8)	0.0308 (7)	0.0036 (6)	0.0119 (5)	0.0043 (6)
C32	0.0323 (7)	0.0488 (9)	0.0311 (7)	0.0003 (6)	0.0116 (6)	0.0020 (6)
C33	0.0305 (8)	0.0721 (12)	0.0321 (7)	0.0052 (7)	0.0077 (6)	0.0128 (7)
C34	0.0380 (8)	0.0595 (11)	0.0486 (9)	0.0164 (8)	0.0169 (7)	0.0223 (8)
C35	0.0405 (8)	0.0429 (9)	0.0588 (10)	0.0112 (7)	0.0148 (7)	0.0103 (7)
C36	0.0339 (8)	0.0384 (8)	0.0448 (8)	0.0033 (6)	0.0083 (6)	0.0033 (6)
O1'	0.0326 (5)	0.0431 (6)	0.0319 (5)	0.0020 (4)	0.0107 (4)	0.0034 (4)
N1'	0.0254 (6)	0.0412 (7)	0.0299 (6)	0.0000 (5)	0.0094 (5)	0.0044 (5)
N2'	0.0263 (6)	0.0341 (6)	0.0338 (6)	−0.0011 (5)	0.0085 (5)	0.0005 (5)
C1'	0.0301 (7)	0.0269 (7)	0.0327 (7)	0.0001 (5)	0.0085 (6)	0.0033 (5)
C2'	0.0301 (7)	0.0279 (7)	0.0300 (7)	0.0002 (5)	0.0093 (5)	−0.0005 (5)
C11'	0.0299 (7)	0.0274 (7)	0.0326 (7)	0.0009 (5)	0.0083 (5)	0.0056 (5)
C12'	0.0351 (8)	0.0310 (7)	0.0374 (7)	0.0002 (6)	0.0104 (6)	0.0002 (6)
C13'	0.0373 (8)	0.0389 (8)	0.0511 (9)	0.0035 (7)	0.0199 (7)	0.0019 (7)
C14'	0.0282 (8)	0.0473 (9)	0.0564 (9)	0.0025 (6)	0.0110 (7)	0.0111 (7)
C15'	0.0322 (8)	0.0566 (10)	0.0399 (8)	−0.0008 (7)	0.0012 (6)	0.0059 (7)
C16'	0.0341 (7)	0.0469 (9)	0.0325 (7)	0.0029 (6)	0.0067 (6)	0.0052 (6)
C21'	0.0225 (6)	0.0382 (8)	0.0284 (6)	−0.0013 (5)	0.0037 (5)	0.0025 (5)
C22'	0.0387 (8)	0.0406 (8)	0.0364 (8)	−0.0030 (6)	0.0074 (6)	0.0029 (6)
C23'	0.0455 (9)	0.0559 (10)	0.0392 (8)	−0.0128 (8)	0.0059 (7)	0.0147 (7)
C24'	0.0371 (9)	0.0819 (13)	0.0339 (8)	−0.0042 (8)	0.0134 (7)	0.0094 (8)
C25'	0.0494 (10)	0.0705 (12)	0.0461 (9)	0.0073 (8)	0.0229 (8)	−0.0038 (8)
C26'	0.0435 (9)	0.0438 (9)	0.0432 (8)	0.0033 (7)	0.0168 (7)	0.0003 (7)
C31'	0.0291 (7)	0.0316 (7)	0.0321 (7)	−0.0015 (6)	0.0095 (5)	−0.0063 (6)
C32'	0.0351 (8)	0.0397 (8)	0.0369 (8)	−0.0047 (6)	0.0125 (6)	−0.0047 (6)
C33'	0.0373 (8)	0.0503 (9)	0.0488 (9)	−0.0099 (7)	0.0199 (7)	−0.0078 (7)
C34'	0.0284 (7)	0.0607 (10)	0.0525 (10)	−0.0072 (7)	0.0131 (7)	−0.0163 (8)
C35'	0.0295 (7)	0.0573 (10)	0.0407 (8)	0.0060 (7)	0.0032 (6)	−0.0083 (7)
C36'	0.0315 (7)	0.0406 (8)	0.0344 (7)	0.0006 (6)	0.0091 (6)	−0.0038 (6)

Geometric parameters (Å, º)

O1—C1	1.2210 (16)	O1'—C1'	1.2224 (15)
N1—C1	1.3583 (17)	N1'—C1'	1.3637 (17)
N1—N2	1.3832 (15)	N1'—N2'	1.3737 (15)
N1—H1	0.930 (17)	N1'—H1'	0.855 (17)
N2—C2	1.2880 (17)	N2'—C2'	1.2871 (16)
C1—C11	1.4937 (19)	C1'—C11'	1.4943 (18)
C2—C31	1.4837 (18)	C2'—C31'	1.4803 (18)
C2—C21	1.4853 (19)	C2'—C21'	1.4969 (18)
C11—C12	1.389 (2)	C11'—C16'	1.3892 (19)
C11—C16	1.3922 (19)	C11'—C12'	1.3945 (19)
C12—C13	1.377 (2)	C12'—C13'	1.385 (2)
C12—H12	0.9500	C12'—H12'	0.9500
C13—C14	1.377 (2)	C13'—C14'	1.379 (2)
C13—H13	0.9500	C13'—H13'	0.9500
C14—C15	1.376 (2)	C14'—C15'	1.381 (2)
C14—H14	0.9500	C14'—H14'	0.9500
C15—C16	1.380 (2)	C15'—C16'	1.385 (2)
C15—H15	0.9500	C15'—H15'	0.9500
C16—H16	0.9500	C16'—H16'	0.9500
C21—C26	1.3899 (19)	C21'—C22'	1.386 (2)
C21—C22	1.391 (2)	C21'—C26'	1.387 (2)
C22—C23	1.378 (2)	C22'—C23'	1.391 (2)
C22—H22	0.9500	C22'—H22'	0.9500
C23—C24	1.374 (3)	C23'—C24'	1.369 (2)
C23—H23	0.9500	C23'—H23'	0.9500
C24—C25	1.380 (3)	C24'—C25'	1.372 (2)
C24—H24	0.9500	C24'—H24'	0.9500
C25—C26	1.386 (2)	C25'—C26'	1.390 (2)
C25—H25	0.9500	C25'—H25'	0.9500
C26—H26	0.9500	C26'—H26'	0.9500
C31—C36	1.391 (2)	C31'—C36'	1.3918 (19)
C31—C32	1.3927 (19)	C31'—C32'	1.3973 (19)
C32—C33	1.382 (2)	C32'—C33'	1.384 (2)
C32—H32	0.9500	C32'—H32'	0.9500
C33—C34	1.382 (2)	C33'—C34'	1.381 (2)
C33—H33	0.9500	C33'—H33'	0.9500
C34—C35	1.373 (2)	C34'—C35'	1.378 (2)
C34—H34	0.9500	C34'—H34'	0.9500
C35—C36	1.386 (2)	C35'—C36'	1.392 (2)
C35—H35	0.9500	C35'—H35'	0.9500
C36—H36	0.9500	C36'—H36'	0.9500
C1—N1—N2	118.71 (11)	C1'—N1'—N2'	119.77 (11)
C1—N1—H1	119.8 (10)	C1'—N1'—H1'	120.7 (10)
N2—N1—H1	120.5 (10)	N2'—N1'—H1'	119.4 (10)
C2—N2—N1	116.16 (11)	C2'—N2'—N1'	116.58 (11)
O1—C1—N1	124.15 (13)	O1'—C1'—N1'	122.72 (12)
O1—C1—C11	121.49 (12)	O1'—C1'—C11'	122.06 (12)
N1—C1—C11	114.34 (11)	N1'—C1'—C11'	115.22 (11)
N2—C2—C31	116.24 (12)	N2'—C2'—C31'	117.27 (11)
N2—C2—C21	125.94 (12)	N2'—C2'—C21'	123.38 (11)
C31—C2—C21	117.79 (11)	C31'—C2'—C21'	119.32 (11)
C12—C11—C16	118.66 (13)	C16'—C11'—C12'	119.18 (13)
C12—C11—C1	123.41 (12)	C16'—C11'—C1'	117.58 (12)
C16—C11—C1	117.91 (12)	C12'—C11'—C1'	123.21 (12)
C13—C12—C11	120.36 (14)	C13'—C12'—C11'	120.26 (13)
C13—C12—H12	119.8	C13'—C12'—H12'	119.9
C11—C12—H12	119.8	C11'—C12'—H12'	119.9
C14—C13—C12	120.56 (15)	C14'—C13'—C12'	119.97 (14)
C14—C13—H13	119.7	C14'—C13'—H13'	120.0
C12—C13—H13	119.7	C12'—C13'—H13'	120.0
C15—C14—C13	119.69 (15)	C13'—C14'—C15'	120.28 (13)
C15—C14—H14	120.2	C13'—C14'—H14'	119.9
C13—C14—H14	120.2	C15'—C14'—H14'	119.9
C14—C15—C16	120.23 (15)	C14'—C15'—C16'	120.03 (14)
C14—C15—H15	119.9	C14'—C15'—H15'	120.0
C16—C15—H15	119.9	C16'—C15'—H15'	120.0
C15—C16—C11	120.49 (14)	C15'—C16'—C11'	120.27 (14)
C15—C16—H16	119.8	C15'—C16'—H16'	119.9
C11—C16—H16	119.8	C11'—C16'—H16'	119.9
C26—C21—C22	119.00 (13)	C22'—C21'—C26'	118.99 (13)
C26—C21—C2	121.17 (13)	C22'—C21'—C2'	120.94 (12)
C22—C21—C2	119.77 (12)	C26'—C21'—C2'	120.06 (12)
C23—C22—C21	120.74 (15)	C21'—C22'—C23'	120.05 (14)
C23—C22—H22	119.6	C21'—C22'—H22'	120.0
C21—C22—H22	119.6	C23'—C22'—H22'	120.0
C24—C23—C22	119.85 (17)	C24'—C23'—C22'	120.47 (15)
C24—C23—H23	120.1	C24'—C23'—H23'	119.8
C22—C23—H23	120.1	C22'—C23'—H23'	119.8
C23—C24—C25	120.29 (16)	C23'—C24'—C25'	120.04 (14)
C23—C24—H24	119.9	C23'—C24'—H24'	120.0
C25—C24—H24	119.9	C25'—C24'—H24'	120.0
C24—C25—C26	120.14 (17)	C24'—C25'—C26'	120.11 (16)
C24—C25—H25	119.9	C24'—C25'—H25'	119.9
C26—C25—H25	119.9	C26'—C25'—H25'	119.9
C25—C26—C21	119.97 (16)	C21'—C26'—C25'	120.33 (15)
C25—C26—H26	120.0	C21'—C26'—H26'	119.8
C21—C26—H26	120.0	C25'—C26'—H26'	119.8
C36—C31—C32	118.96 (13)	C36'—C31'—C32'	118.77 (12)
C36—C31—C2	119.41 (12)	C36'—C31'—C2'	120.91 (12)
C32—C31—C2	121.51 (13)	C32'—C31'—C2'	120.31 (12)
C33—C32—C31	119.83 (14)	C33'—C32'—C31'	120.50 (14)
C33—C32—H32	120.1	C33'—C32'—H32'	119.7
C31—C32—H32	120.1	C31'—C32'—H32'	119.7
C34—C33—C32	120.86 (14)	C34'—C33'—C32'	120.03 (14)
C34—C33—H33	119.6	C34'—C33'—H33'	120.0
C32—C33—H33	119.6	C32'—C33'—H33'	120.0
C35—C34—C33	119.50 (14)	C35'—C34'—C33'	120.31 (14)
C35—C34—H34	120.2	C35'—C34'—H34'	119.8
C33—C34—H34	120.2	C33'—C34'—H34'	119.8
C34—C35—C36	120.38 (16)	C34'—C35'—C36'	119.97 (15)
C34—C35—H35	119.8	C34'—C35'—H35'	120.0
C36—C35—H35	119.8	C36'—C35'—H35'	120.0
C35—C36—C31	120.37 (14)	C35'—C36'—C31'	120.40 (14)
C35—C36—H36	119.8	C35'—C36'—H36'	119.8
C31—C36—H36	119.8	C31'—C36'—H36'	119.8
C1—N1—N2—C2	169.23 (12)	C1'—N1'—N2'—C2'	175.22 (12)
N2—N1—C1—O1	0.6 (2)	N2'—N1'—C1'—O1'	−6.0 (2)
N2—N1—C1—C11	−178.00 (11)	N2'—N1'—C1'—C11'	173.78 (11)
N1—N2—C2—C31	177.79 (11)	N1'—N2'—C2'—C31'	176.22 (11)
N1—N2—C2—C21	−4.40 (19)	N1'—N2'—C2'—C21'	−1.51 (19)
O1—C1—C11—C12	−153.42 (14)	O1'—C1'—C11'—C16'	−25.23 (19)
N1—C1—C11—C12	25.25 (19)	N1'—C1'—C11'—C16'	155.01 (12)
O1—C1—C11—C16	25.2 (2)	O1'—C1'—C11'—C12'	152.74 (13)
N1—C1—C11—C16	−156.09 (12)	N1'—C1'—C11'—C12'	−27.02 (19)
C16—C11—C12—C13	0.9 (2)	C16'—C11'—C12'—C13'	−0.1 (2)
C1—C11—C12—C13	179.51 (14)	C1'—C11'—C12'—C13'	−178.02 (13)
C11—C12—C13—C14	−0.6 (3)	C11'—C12'—C13'—C14'	−0.2 (2)
C12—C13—C14—C15	−0.1 (3)	C12'—C13'—C14'—C15'	−0.2 (2)
C13—C14—C15—C16	0.5 (3)	C13'—C14'—C15'—C16'	0.8 (2)
C14—C15—C16—C11	−0.2 (2)	C14'—C15'—C16'—C11'	−1.1 (2)
C12—C11—C16—C15	−0.5 (2)	C12'—C11'—C16'—C15'	0.8 (2)
C1—C11—C16—C15	−179.22 (13)	C1'—C11'—C16'—C15'	178.82 (14)
N2—C2—C21—C26	−58.02 (19)	N2'—C2'—C21'—C22'	−91.72 (17)
C31—C2—C21—C26	119.76 (14)	C31'—C2'—C21'—C22'	90.60 (16)
N2—C2—C21—C22	124.86 (15)	N2'—C2'—C21'—C26'	87.16 (17)
C31—C2—C21—C22	−57.36 (17)	C31'—C2'—C21'—C26'	−90.52 (16)
C26—C21—C22—C23	1.5 (2)	C26'—C21'—C22'—C23'	0.3 (2)
C2—C21—C22—C23	178.70 (13)	C2'—C21'—C22'—C23'	179.17 (13)
C21—C22—C23—C24	−1.8 (2)	C21'—C22'—C23'—C24'	−0.4 (2)
C22—C23—C24—C25	0.7 (3)	C22'—C23'—C24'—C25'	0.5 (2)
C23—C24—C25—C26	0.7 (3)	C23'—C24'—C25'—C26'	−0.4 (3)
C24—C25—C26—C21	−0.9 (2)	C22'—C21'—C26'—C25'	−0.2 (2)
C22—C21—C26—C25	−0.2 (2)	C2'—C21'—C26'—C25'	−179.12 (14)
C2—C21—C26—C25	−177.34 (13)	C24'—C25'—C26'—C21'	0.3 (2)
N2—C2—C31—C36	143.29 (13)	N2'—C2'—C31'—C36'	158.77 (12)
C21—C2—C31—C36	−34.71 (18)	C21'—C2'—C31'—C36'	−23.41 (19)
N2—C2—C31—C32	−32.76 (18)	N2'—C2'—C31'—C32'	−22.56 (19)
C21—C2—C31—C32	149.24 (13)	C21'—C2'—C31'—C32'	155.26 (12)
C36—C31—C32—C33	−2.5 (2)	C36'—C31'—C32'—C33'	−0.3 (2)
C2—C31—C32—C33	173.54 (13)	C2'—C31'—C32'—C33'	−178.95 (13)
C31—C32—C33—C34	−0.1 (2)	C31'—C32'—C33'—C34'	0.3 (2)
C32—C33—C34—C35	1.9 (2)	C32'—C33'—C34'—C35'	−0.6 (2)
C33—C34—C35—C36	−1.1 (2)	C33'—C34'—C35'—C36'	1.0 (2)
C34—C35—C36—C31	−1.5 (2)	C34'—C35'—C36'—C31'	−1.0 (2)
C32—C31—C36—C35	3.3 (2)	C32'—C31'—C36'—C35'	0.6 (2)
C2—C31—C36—C35	−172.82 (13)	C2'—C31'—C36'—C35'	179.30 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1′	0.930 (17)	2.168 (17)	3.0846 (15)	168.5 (14)
C12—H12···O1′	0.95	2.52	2.9884 (17)	111
C34—H34···O1^i	0.95	2.58	3.5238 (18)	171

Symmetry code: (i) −x+1, −y+2, −z.

(VI) 1-Benzoyl-2-[1-(4-chlorophenyl)benzylidene]hydrazone

Crystal data

C20H15ClN2O	Z = 8
Mr = 334.79	F(000) = 1392
Monoclinic, P21/n	Dx = 1.344 Mg m^−3
a = 19.432 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9330 (18) Å	µ = 0.24 mm^−1
c = 19.496 (4) Å	T = 173 K
β = 102.18 (3)°	Block, colourless
V = 3308.1 (12) Å^3	0.56 × 0.48 × 0.31 mm

Data collection

Stoe IPDS II two-circle diffractometer	4590 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.074
Graphite monochromator	θmax = 26.0°, θmin = 2.7°
φ scans	h = −23→23
46062 measured reflections	k = −10→10
6453 independent reflections	l = −24→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	w = 1/[σ^2(Fo^2) + (0.030P)^2] where P = (Fo^2 + 2Fc^2)/3
6453 reflections	(Δ/σ)max = 0.001
441 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.24104 (4)	0.03180 (9)	0.22787 (4)	0.0817 (2)
O1	0.56343 (7)	0.56746 (17)	0.08803 (7)	0.0470 (3)
N1	0.44952 (8)	0.6375 (2)	0.04511 (9)	0.0392 (4)
H1	0.4193 (12)	0.706 (3)	0.0155 (11)	0.056 (7)*
N2	0.42312 (8)	0.52314 (19)	0.07895 (8)	0.0393 (4)
C1	0.52100 (10)	0.6485 (2)	0.04991 (10)	0.0391 (5)
C2	0.35518 (10)	0.5124 (2)	0.06926 (10)	0.0381 (4)
C11	0.54334 (10)	0.7694 (2)	0.00645 (10)	0.0410 (5)
C12	0.49973 (11)	0.8309 (2)	−0.05241 (10)	0.0471 (5)
H12	0.4525	0.7973	−0.0668	0.056*
C13	0.52539 (13)	0.9415 (3)	−0.09007 (12)	0.0560 (6)
H13	0.4956	0.9839	−0.1303	0.067*
C14	0.59419 (14)	0.9905 (3)	−0.06951 (13)	0.0597 (6)
H14	0.6115	1.0665	−0.0955	0.072*
C15	0.63742 (13)	0.9292 (3)	−0.01152 (14)	0.0623 (7)
H15	0.6847	0.9627	0.0026	0.075*
C16	0.61240 (11)	0.8193 (3)	0.02623 (12)	0.0517 (6)
H16	0.6427	0.7771	0.0662	0.062*
C21	0.30470 (10)	0.6146 (2)	0.02279 (10)	0.0392 (5)
C22	0.26304 (11)	0.7133 (2)	0.05217 (12)	0.0475 (5)
H22	0.2660	0.7138	0.1014	0.057*
C23	0.21760 (11)	0.8100 (3)	0.00940 (13)	0.0528 (6)
H23	0.1900	0.8783	0.0295	0.063*
C24	0.21218 (11)	0.8079 (3)	−0.06229 (14)	0.0559 (6)
H24	0.1805	0.8739	−0.0914	0.067*
C25	0.25248 (11)	0.7107 (3)	−0.09160 (12)	0.0529 (6)
H25	0.2485	0.7093	−0.1410	0.064*
C26	0.29921 (11)	0.6141 (2)	−0.04922 (11)	0.0452 (5)
H26	0.3274	0.5478	−0.0697	0.054*
C31	0.32717 (10)	0.3934 (2)	0.10856 (10)	0.0385 (4)
C32	0.37082 (11)	0.3217 (2)	0.16447 (10)	0.0442 (5)
H32	0.4189	0.3497	0.1778	0.053*
C33	0.34491 (12)	0.2103 (2)	0.20070 (11)	0.0491 (5)
H33	0.3749	0.1611	0.2388	0.059*
C34	0.27410 (12)	0.1702 (3)	0.18085 (11)	0.0504 (5)
C35	0.23008 (11)	0.2391 (3)	0.12546 (12)	0.0492 (5)
H35	0.1821	0.2100	0.1121	0.059*
C36	0.25615 (11)	0.3502 (2)	0.08983 (11)	0.0430 (5)
H36	0.2258	0.3989	0.0518	0.052*
Cl1'	0.71520 (3)	0.54781 (7)	0.23796 (3)	0.06059 (16)
O1'	0.61656 (7)	−0.02612 (16)	0.56664 (7)	0.0435 (3)
N1'	0.56737 (9)	−0.09548 (19)	0.45548 (8)	0.0377 (4)
H1'	0.5415 (11)	−0.161 (2)	0.4276 (11)	0.045*
N2'	0.59881 (8)	0.02004 (18)	0.42680 (8)	0.0377 (4)
C1'	0.57913 (10)	−0.1112 (2)	0.52639 (9)	0.0343 (4)
C2'	0.58456 (10)	0.0303 (2)	0.35943 (9)	0.0360 (4)
C11'	0.54246 (10)	−0.2406 (2)	0.55113 (10)	0.0366 (4)
C12'	0.47518 (11)	−0.2876 (2)	0.51814 (10)	0.0403 (5)
H12'	0.4517	−0.2410	0.4758	0.048*
C13'	0.44252 (12)	−0.4025 (2)	0.54712 (12)	0.0479 (5)
H13'	0.3963	−0.4330	0.5250	0.057*
C14'	0.47655 (13)	−0.4724 (3)	0.60743 (12)	0.0523 (6)
H14'	0.4542	−0.5517	0.6268	0.063*
C15'	0.54352 (13)	−0.4269 (3)	0.63997 (11)	0.0549 (6)
H15'	0.5672	−0.4757	0.6816	0.066*
C16'	0.57640 (11)	−0.3109 (2)	0.61238 (10)	0.0449 (5)
H16'	0.6222	−0.2795	0.6354	0.054*
C21'	0.53733 (11)	−0.0741 (2)	0.31215 (9)	0.0372 (4)
C22'	0.56492 (12)	−0.1709 (2)	0.26916 (10)	0.0485 (5)
H22'	0.6136	−0.1673	0.2682	0.058*
C23'	0.52069 (16)	−0.2738 (3)	0.22731 (11)	0.0616 (7)
H23'	0.5394	−0.3417	0.1985	0.074*
C24'	0.44943 (16)	−0.2767 (3)	0.22789 (12)	0.0618 (7)
H24'	0.4194	−0.3459	0.1989	0.074*
C25'	0.42208 (13)	−0.1813 (3)	0.26963 (11)	0.0547 (6)
H25'	0.3732	−0.1840	0.2695	0.066*
C26'	0.46501 (11)	−0.0814 (2)	0.31182 (10)	0.0448 (5)
H26'	0.4456	−0.0161	0.3413	0.054*
C31'	0.61802 (10)	0.1565 (2)	0.32892 (10)	0.0372 (4)
C32'	0.68001 (11)	0.2224 (2)	0.36577 (11)	0.0420 (5)
H32'	0.7021	0.1845	0.4105	0.050*
C33'	0.70960 (11)	0.3428 (2)	0.33759 (11)	0.0443 (5)
H33'	0.7519	0.3873	0.3626	0.053*
C34'	0.67673 (11)	0.3972 (2)	0.27263 (10)	0.0432 (5)
C35'	0.61536 (12)	0.3350 (2)	0.23533 (10)	0.0470 (5)
H35'	0.5930	0.3744	0.1909	0.056*
C36'	0.58676 (11)	0.2139 (2)	0.26376 (10)	0.0427 (5)
H36'	0.5448	0.1692	0.2381	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0716 (4)	0.0801 (5)	0.0964 (5)	0.0007 (4)	0.0245 (4)	0.0435 (4)
O1	0.0393 (8)	0.0561 (9)	0.0445 (8)	0.0078 (7)	0.0066 (6)	0.0017 (7)
N1	0.0352 (9)	0.0382 (10)	0.0434 (9)	0.0012 (8)	0.0066 (7)	−0.0004 (8)
N2	0.0391 (10)	0.0388 (10)	0.0403 (9)	0.0024 (8)	0.0093 (7)	−0.0058 (7)
C1	0.0337 (11)	0.0455 (12)	0.0369 (10)	0.0017 (9)	0.0046 (8)	−0.0117 (9)
C2	0.0364 (11)	0.0395 (12)	0.0378 (10)	0.0036 (9)	0.0069 (8)	−0.0063 (9)
C11	0.0414 (12)	0.0397 (12)	0.0426 (11)	0.0000 (9)	0.0107 (9)	−0.0106 (9)
C12	0.0495 (13)	0.0470 (13)	0.0440 (12)	−0.0005 (11)	0.0084 (10)	−0.0079 (10)
C13	0.0743 (17)	0.0492 (15)	0.0462 (12)	0.0033 (13)	0.0164 (11)	−0.0055 (11)
C14	0.0801 (18)	0.0442 (14)	0.0618 (15)	−0.0107 (13)	0.0313 (14)	−0.0104 (12)
C15	0.0555 (15)	0.0589 (16)	0.0753 (17)	−0.0160 (13)	0.0204 (13)	−0.0099 (14)
C16	0.0417 (12)	0.0535 (15)	0.0582 (13)	−0.0058 (11)	0.0071 (10)	−0.0075 (11)
C21	0.0319 (10)	0.0381 (11)	0.0476 (12)	0.0011 (9)	0.0085 (8)	0.0012 (9)
C22	0.0467 (12)	0.0428 (13)	0.0566 (13)	0.0013 (11)	0.0191 (10)	0.0039 (11)
C23	0.0416 (12)	0.0394 (13)	0.0829 (17)	0.0089 (10)	0.0252 (11)	0.0130 (12)
C24	0.0349 (12)	0.0501 (15)	0.0810 (18)	−0.0006 (10)	0.0079 (11)	0.0209 (13)
C25	0.0449 (13)	0.0592 (15)	0.0507 (13)	−0.0017 (12)	0.0012 (10)	0.0098 (11)
C26	0.0402 (11)	0.0485 (13)	0.0465 (12)	−0.0005 (10)	0.0079 (9)	−0.0005 (10)
C31	0.0404 (11)	0.0370 (11)	0.0390 (10)	0.0056 (9)	0.0102 (8)	−0.0040 (9)
C32	0.0455 (12)	0.0412 (12)	0.0445 (11)	0.0044 (10)	0.0065 (9)	−0.0015 (10)
C33	0.0549 (14)	0.0472 (14)	0.0428 (12)	0.0095 (11)	0.0051 (10)	0.0045 (10)
C34	0.0528 (14)	0.0474 (13)	0.0546 (13)	0.0019 (11)	0.0191 (11)	0.0063 (11)
C35	0.0396 (12)	0.0518 (14)	0.0565 (13)	0.0029 (10)	0.0110 (10)	0.0063 (11)
C36	0.0395 (12)	0.0446 (13)	0.0439 (11)	0.0061 (10)	0.0067 (9)	0.0017 (10)
Cl1'	0.0725 (4)	0.0534 (4)	0.0591 (4)	−0.0169 (3)	0.0211 (3)	0.0046 (3)
O1'	0.0437 (8)	0.0501 (9)	0.0359 (7)	−0.0080 (7)	0.0067 (6)	−0.0024 (7)
N1'	0.0446 (10)	0.0340 (10)	0.0334 (9)	−0.0008 (8)	0.0059 (7)	0.0002 (7)
N2'	0.0416 (9)	0.0352 (9)	0.0378 (9)	0.0030 (8)	0.0113 (7)	0.0013 (7)
C1'	0.0316 (10)	0.0390 (11)	0.0322 (10)	0.0048 (9)	0.0069 (8)	−0.0029 (9)
C2'	0.0392 (10)	0.0340 (10)	0.0354 (10)	0.0076 (9)	0.0094 (8)	0.0000 (9)
C11'	0.0401 (11)	0.0343 (11)	0.0366 (10)	0.0034 (9)	0.0109 (8)	−0.0033 (9)
C12'	0.0443 (11)	0.0358 (12)	0.0408 (11)	0.0020 (9)	0.0090 (9)	−0.0039 (9)
C13'	0.0462 (12)	0.0427 (13)	0.0557 (13)	−0.0062 (10)	0.0128 (10)	−0.0097 (10)
C14'	0.0679 (15)	0.0387 (13)	0.0564 (13)	−0.0076 (11)	0.0272 (12)	−0.0001 (11)
C15'	0.0712 (16)	0.0518 (15)	0.0435 (12)	0.0028 (13)	0.0164 (11)	0.0112 (11)
C16'	0.0449 (11)	0.0492 (13)	0.0396 (11)	0.0047 (10)	0.0071 (9)	0.0039 (10)
C21'	0.0507 (12)	0.0317 (11)	0.0301 (9)	0.0038 (9)	0.0104 (8)	0.0029 (8)
C22'	0.0643 (14)	0.0437 (13)	0.0397 (11)	0.0105 (11)	0.0162 (10)	0.0012 (10)
C23'	0.111 (2)	0.0381 (14)	0.0348 (12)	0.0109 (14)	0.0121 (13)	−0.0040 (10)
C24'	0.092 (2)	0.0458 (15)	0.0400 (13)	−0.0149 (14)	−0.0022 (13)	0.0006 (11)
C25'	0.0600 (14)	0.0578 (15)	0.0415 (12)	−0.0139 (12)	−0.0002 (10)	0.0020 (11)
C26'	0.0538 (13)	0.0440 (13)	0.0369 (11)	0.0014 (10)	0.0105 (9)	0.0003 (9)
C31'	0.0426 (11)	0.0339 (11)	0.0364 (10)	0.0025 (9)	0.0113 (8)	−0.0007 (9)
C32'	0.0426 (12)	0.0431 (12)	0.0406 (11)	0.0046 (10)	0.0095 (9)	0.0037 (9)
C33'	0.0415 (11)	0.0433 (12)	0.0477 (12)	−0.0020 (10)	0.0085 (9)	−0.0039 (10)
C34'	0.0535 (13)	0.0360 (11)	0.0437 (11)	−0.0029 (10)	0.0186 (9)	0.0007 (9)
C35'	0.0591 (14)	0.0458 (14)	0.0354 (11)	−0.0005 (11)	0.0086 (10)	0.0020 (10)
C36'	0.0463 (12)	0.0400 (12)	0.0407 (11)	−0.0042 (10)	0.0066 (9)	−0.0008 (9)

Geometric parameters (Å, º)

Cl1—C34	1.741 (2)	Cl1'—C34'	1.744 (2)
O1—C1	1.224 (2)	O1'—C1'	1.217 (2)
N1—N2	1.373 (2)	N1'—C1'	1.360 (2)
N1—C1	1.376 (2)	N1'—N2'	1.376 (2)
N1—H1	0.95 (2)	N1'—H1'	0.88 (2)
N2—C2	1.297 (2)	N2'—C2'	1.287 (2)
C1—C11	1.492 (3)	C1'—C11'	1.491 (3)
C2—C31	1.479 (3)	C2'—C21'	1.485 (3)
C2—C21	1.497 (3)	C2'—C31'	1.486 (3)
C11—C12	1.388 (3)	C11'—C16'	1.387 (3)
C11—C16	1.389 (3)	C11'—C12'	1.394 (3)
C12—C13	1.385 (3)	C12'—C13'	1.388 (3)
C12—H12	0.9500	C12'—H12'	0.9500
C13—C14	1.383 (3)	C13'—C14'	1.372 (3)
C13—H13	0.9500	C13'—H13'	0.9500
C14—C15	1.372 (3)	C14'—C15'	1.383 (3)
C14—H14	0.9500	C14'—H14'	0.9500
C15—C16	1.376 (3)	C15'—C16'	1.384 (3)
C15—H15	0.9500	C15'—H15'	0.9500
C16—H16	0.9500	C16'—H16'	0.9500
C21—C26	1.385 (3)	C21'—C22'	1.389 (3)
C21—C22	1.399 (3)	C21'—C26'	1.405 (3)
C22—C23	1.383 (3)	C22'—C23'	1.397 (3)
C22—H22	0.9500	C22'—H22'	0.9500
C23—C24	1.379 (3)	C23'—C24'	1.387 (4)
C23—H23	0.9500	C23'—H23'	0.9500
C24—C25	1.372 (3)	C24'—C25'	1.361 (4)
C24—H24	0.9500	C24'—H24'	0.9500
C25—C26	1.391 (3)	C25'—C26'	1.371 (3)
C25—H25	0.9500	C25'—H25'	0.9500
C26—H26	0.9500	C26'—H26'	0.9500
C31—C32	1.389 (3)	C31'—C36'	1.386 (3)
C31—C36	1.405 (3)	C31'—C32'	1.396 (3)
C32—C33	1.376 (3)	C32'—C33'	1.387 (3)
C32—H32	0.9500	C32'—H32'	0.9500
C33—C34	1.395 (3)	C33'—C34'	1.380 (3)
C33—H33	0.9500	C33'—H33'	0.9500
C34—C35	1.374 (3)	C34'—C35'	1.376 (3)
C35—C36	1.368 (3)	C35'—C36'	1.384 (3)
C35—H35	0.9500	C35'—H35'	0.9500
C36—H36	0.9500	C36'—H36'	0.9500
N2—N1—C1	119.67 (17)	C1'—N1'—N2'	119.75 (17)
N2—N1—H1	121.6 (13)	C1'—N1'—H1'	120.6 (13)
C1—N1—H1	118.6 (13)	N2'—N1'—H1'	119.5 (13)
C2—N2—N1	117.22 (17)	C2'—N2'—N1'	116.72 (16)
O1—C1—N1	122.68 (19)	O1'—C1'—N1'	122.72 (18)
O1—C1—C11	122.24 (18)	O1'—C1'—C11'	122.49 (17)
N1—C1—C11	115.06 (18)	N1'—C1'—C11'	114.79 (17)
N2—C2—C31	116.89 (18)	N2'—C2'—C21'	124.07 (17)
N2—C2—C21	124.03 (18)	N2'—C2'—C31'	116.39 (17)
C31—C2—C21	119.07 (17)	C21'—C2'—C31'	119.54 (16)
C12—C11—C16	119.2 (2)	C16'—C11'—C12'	119.35 (19)
C12—C11—C1	123.76 (18)	C16'—C11'—C1'	117.18 (17)
C16—C11—C1	117.01 (19)	C12'—C11'—C1'	123.37 (17)
C13—C12—C11	119.7 (2)	C13'—C12'—C11'	119.98 (19)
C13—C12—H12	120.2	C13'—C12'—H12'	120.0
C11—C12—H12	120.2	C11'—C12'—H12'	120.0
C14—C13—C12	120.4 (2)	C14'—C13'—C12'	120.4 (2)
C14—C13—H13	119.8	C14'—C13'—H13'	119.8
C12—C13—H13	119.8	C12'—C13'—H13'	119.8
C15—C14—C13	119.9 (2)	C13'—C14'—C15'	119.8 (2)
C15—C14—H14	120.0	C13'—C14'—H14'	120.1
C13—C14—H14	120.0	C15'—C14'—H14'	120.1
C14—C15—C16	120.1 (2)	C14'—C15'—C16'	120.5 (2)
C14—C15—H15	120.0	C14'—C15'—H15'	119.7
C16—C15—H15	120.0	C16'—C15'—H15'	119.7
C15—C16—C11	120.7 (2)	C15'—C16'—C11'	119.9 (2)
C15—C16—H16	119.7	C15'—C16'—H16'	120.0
C11—C16—H16	119.7	C11'—C16'—H16'	120.0
C26—C21—C22	119.3 (2)	C22'—C21'—C26'	118.76 (19)
C26—C21—C2	120.79 (18)	C22'—C21'—C2'	119.96 (19)
C22—C21—C2	119.89 (18)	C26'—C21'—C2'	121.24 (17)
C23—C22—C21	119.9 (2)	C21'—C22'—C23'	119.6 (2)
C23—C22—H22	120.1	C21'—C22'—H22'	120.2
C21—C22—H22	120.1	C23'—C22'—H22'	120.2
C24—C23—C22	120.3 (2)	C24'—C23'—C22'	120.0 (2)
C24—C23—H23	119.8	C24'—C23'—H23'	120.0
C22—C23—H23	119.8	C22'—C23'—H23'	120.0
C25—C24—C23	120.2 (2)	C25'—C24'—C23'	120.6 (2)
C25—C24—H24	119.9	C25'—C24'—H24'	119.7
C23—C24—H24	119.9	C23'—C24'—H24'	119.7
C24—C25—C26	120.2 (2)	C24'—C25'—C26'	120.1 (2)
C24—C25—H25	119.9	C24'—C25'—H25'	120.0
C26—C25—H25	119.9	C26'—C25'—H25'	120.0
C21—C26—C25	120.1 (2)	C25'—C26'—C21'	121.0 (2)
C21—C26—H26	120.0	C25'—C26'—H26'	119.5
C25—C26—H26	120.0	C21'—C26'—H26'	119.5
C32—C31—C36	118.76 (19)	C36'—C31'—C32'	118.63 (18)
C32—C31—C2	120.50 (18)	C36'—C31'—C2'	120.22 (18)
C36—C31—C2	120.74 (18)	C32'—C31'—C2'	121.12 (17)
C33—C32—C31	120.5 (2)	C33'—C32'—C31'	120.6 (2)
C33—C32—H32	119.7	C33'—C32'—H32'	119.7
C31—C32—H32	119.7	C31'—C32'—H32'	119.7
C32—C33—C34	119.3 (2)	C34'—C33'—C32'	119.1 (2)
C32—C33—H33	120.3	C34'—C33'—H33'	120.5
C34—C33—H33	120.3	C32'—C33'—H33'	120.5
C35—C34—C33	121.2 (2)	C35'—C34'—C33'	121.65 (18)
C35—C34—Cl1	119.63 (17)	C35'—C34'—Cl1'	120.08 (16)
C33—C34—Cl1	119.21 (17)	C33'—C34'—Cl1'	118.27 (16)
C36—C35—C34	119.2 (2)	C34'—C35'—C36'	118.69 (19)
C36—C35—H35	120.4	C34'—C35'—H35'	120.7
C34—C35—H35	120.4	C36'—C35'—H35'	120.7
C35—C36—C31	121.0 (2)	C35'—C36'—C31'	121.4 (2)
C35—C36—H36	119.5	C35'—C36'—H36'	119.3
C31—C36—H36	119.5	C31'—C36'—H36'	119.3
C1—N1—N2—C2	−175.88 (16)	C1'—N1'—N2'—C2'	−178.78 (17)
N2—N1—C1—O1	−6.2 (3)	N2'—N1'—C1'—O1'	0.3 (3)
N2—N1—C1—C11	175.27 (16)	N2'—N1'—C1'—C11'	−179.78 (15)
N1—N2—C2—C31	−177.15 (16)	N1'—N2'—C2'—C21'	−0.3 (3)
N1—N2—C2—C21	1.2 (3)	N1'—N2'—C2'—C31'	179.27 (16)
O1—C1—C11—C12	158.76 (19)	O1'—C1'—C11'—C16'	−33.1 (3)
N1—C1—C11—C12	−22.7 (3)	N1'—C1'—C11'—C16'	147.07 (17)
O1—C1—C11—C16	−19.9 (3)	O1'—C1'—C11'—C12'	143.27 (19)
N1—C1—C11—C16	158.67 (17)	N1'—C1'—C11'—C12'	−36.6 (3)
C16—C11—C12—C13	−0.5 (3)	C16'—C11'—C12'—C13'	0.8 (3)
C1—C11—C12—C13	−179.14 (19)	C1'—C11'—C12'—C13'	−175.49 (18)
C11—C12—C13—C14	0.2 (3)	C11'—C12'—C13'—C14'	−1.2 (3)
C12—C13—C14—C15	0.1 (3)	C12'—C13'—C14'—C15'	0.7 (3)
C13—C14—C15—C16	−0.1 (4)	C13'—C14'—C15'—C16'	0.4 (3)
C14—C15—C16—C11	−0.2 (3)	C14'—C15'—C16'—C11'	−0.8 (3)
C12—C11—C16—C15	0.5 (3)	C12'—C11'—C16'—C15'	0.3 (3)
C1—C11—C16—C15	179.2 (2)	C1'—C11'—C16'—C15'	176.74 (19)
N2—C2—C21—C26	66.8 (3)	N2'—C2'—C21'—C22'	−111.6 (2)
C31—C2—C21—C26	−114.9 (2)	C31'—C2'—C21'—C22'	68.8 (2)
N2—C2—C21—C22	−112.4 (2)	N2'—C2'—C21'—C26'	65.9 (3)
C31—C2—C21—C22	65.9 (3)	C31'—C2'—C21'—C26'	−113.7 (2)
C26—C21—C22—C23	−0.7 (3)	C26'—C21'—C22'—C23'	−0.6 (3)
C2—C21—C22—C23	178.52 (19)	C2'—C21'—C22'—C23'	176.94 (18)
C21—C22—C23—C24	1.2 (3)	C21'—C22'—C23'—C24'	1.2 (3)
C22—C23—C24—C25	−0.7 (3)	C22'—C23'—C24'—C25'	−0.8 (4)
C23—C24—C25—C26	−0.2 (3)	C23'—C24'—C25'—C26'	−0.2 (4)
C22—C21—C26—C25	−0.2 (3)	C24'—C25'—C26'—C21'	0.8 (3)
C2—C21—C26—C25	−179.45 (19)	C22'—C21'—C26'—C25'	−0.4 (3)
C24—C25—C26—C21	0.7 (3)	C2'—C21'—C26'—C25'	−177.95 (19)
N2—C2—C31—C32	14.5 (3)	N2'—C2'—C31'—C36'	−154.13 (18)
C21—C2—C31—C32	−163.90 (18)	C21'—C2'—C31'—C36'	25.5 (3)
N2—C2—C31—C36	−165.07 (18)	N2'—C2'—C31'—C32'	23.9 (3)
C21—C2—C31—C36	16.5 (3)	C21'—C2'—C31'—C32'	−156.48 (18)
C36—C31—C32—C33	0.1 (3)	C36'—C31'—C32'—C33'	−0.1 (3)
C2—C31—C32—C33	−179.51 (19)	C2'—C31'—C32'—C33'	−178.13 (18)
C31—C32—C33—C34	−0.2 (3)	C31'—C32'—C33'—C34'	0.3 (3)
C32—C33—C34—C35	0.6 (3)	C32'—C33'—C34'—C35'	0.1 (3)
C32—C33—C34—Cl1	−178.74 (17)	C32'—C33'—C34'—Cl1'	−179.58 (15)
C33—C34—C35—C36	−0.8 (3)	C33'—C34'—C35'—C36'	−0.8 (3)
Cl1—C34—C35—C36	178.51 (17)	Cl1'—C34'—C35'—C36'	178.93 (16)
C34—C35—C36—C31	0.7 (3)	C34'—C35'—C36'—C31'	1.0 (3)
C32—C31—C36—C35	−0.3 (3)	C32'—C31'—C36'—C35'	−0.6 (3)
C2—C31—C36—C35	179.28 (19)	C2'—C31'—C36'—C35'	177.48 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···O1^i	0.95	2.45	3.344 (3)	156
C36—H36···O1′^ii	0.95	2.48	3.085 (2)	122
C26′—H26′···O1′^iii	0.95	2.40	3.261 (2)	151
C23′—H23′···O1^iv	0.95	2.44	3.320 (3)	155

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+1, −y, −z+1; (iv) x, y−1, z.

(VII) 1-Benzoyl-2-(4-hydroxybenzylidene)hydrazone methanol monosolvate

Crystal data

C15H16N2O3	F(000) = 1152
Mr = 272.30	Dx = 1.317 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 13.382 (1) Å	µ = 0.09 mm^−1
b = 8.8183 (8) Å	T = 173 K
c = 23.275 (2) Å	Block, colourless
V = 2746.6 (4) Å^3	0.53 × 0.32 × 0.24 mm
Z = 8

Data collection

Stoe IPDS II two-circle diffractometer	1723 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.083
Graphite monochromator	θmax = 26.2°, θmin = 2.9°
φ scans	h = −16→16
33745 measured reflections	k = −10→10
2745 independent reflections	l = −28→28

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 0.80	w = 1/[σ^2(Fo^2) + (0.040P)^2] where P = (Fo^2 + 2Fc^2)/3
2745 reflections	(Δ/σ)max = 0.001
194 parameters	Δρmax = 0.11 e Å^−3
0 restraints	Δρmin = −0.14 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.10051 (6)	0.08546 (11)	0.59724 (5)	0.0421 (3)
O1M	0.05577 (7)	0.38329 (14)	0.62681 (6)	0.0554 (3)
H1M	0.0570 (14)	0.295 (3)	0.6132 (9)	0.080 (7)*
O24	0.05235 (8)	−0.58837 (11)	0.86095 (4)	0.0404 (3)
H24	−0.0080 (15)	−0.560 (2)	0.8666 (8)	0.076 (6)*
N1	0.24168 (8)	−0.02072 (13)	0.63224 (5)	0.0341 (3)
H1	0.3087 (12)	−0.0398 (18)	0.6281 (7)	0.049 (4)*
N2	0.18584 (8)	−0.10638 (13)	0.67050 (5)	0.0348 (3)
C1	0.19293 (9)	0.07050 (15)	0.59559 (6)	0.0350 (3)
C1M	−0.04218 (11)	0.44398 (19)	0.62818 (8)	0.0540 (4)
H1M1	−0.0865	0.3739	0.6486	0.081*
H1M2	−0.0664	0.4580	0.5888	0.081*
H1M3	−0.0414	0.5420	0.6480	0.081*
C2	0.23587 (10)	−0.18945 (16)	0.70517 (6)	0.0354 (3)
H2	0.3068	−0.1850	0.7046	0.042*
C11	0.25400 (10)	0.15414 (15)	0.55282 (6)	0.0354 (3)
C12	0.35464 (10)	0.18663 (18)	0.56073 (7)	0.0435 (4)
H12	0.3884	0.1516	0.5941	0.052*
C13	0.40573 (12)	0.2704 (2)	0.51974 (8)	0.0522 (4)
H13	0.4743	0.2935	0.5255	0.063*
C14	0.35858 (13)	0.32052 (19)	0.47102 (8)	0.0546 (4)
H14	0.3942	0.3779	0.4432	0.066*
C15	0.25931 (14)	0.2871 (2)	0.46273 (8)	0.0623 (5)
H15	0.2263	0.3200	0.4288	0.075*
C16	0.20742 (12)	0.2057 (2)	0.50377 (8)	0.0528 (4)
H16	0.1385	0.1849	0.4981	0.063*
C21	0.18612 (10)	−0.29064 (15)	0.74545 (6)	0.0335 (3)
C22	0.08210 (9)	−0.31096 (16)	0.74536 (6)	0.0369 (3)
H22	0.0422	−0.2561	0.7188	0.044*
C23	0.03710 (10)	−0.40919 (16)	0.78322 (6)	0.0377 (3)
H23	−0.0334	−0.4218	0.7825	0.045*
C24	0.09420 (9)	−0.49014 (15)	0.82253 (6)	0.0330 (3)
C25	0.19744 (9)	−0.47251 (16)	0.82312 (7)	0.0369 (3)
H25	0.2371	−0.5281	0.8496	0.044*
C26	0.24187 (10)	−0.37353 (17)	0.78486 (6)	0.0369 (3)
H26	0.3124	−0.3618	0.7855	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0279 (5)	0.0437 (6)	0.0545 (7)	0.0035 (4)	0.0056 (4)	0.0030 (5)
O1M	0.0283 (5)	0.0447 (7)	0.0930 (10)	0.0016 (5)	0.0000 (5)	−0.0093 (7)
O24	0.0340 (5)	0.0423 (6)	0.0448 (6)	0.0015 (5)	0.0049 (5)	0.0062 (5)
N1	0.0274 (6)	0.0358 (6)	0.0391 (7)	0.0000 (5)	0.0046 (5)	0.0011 (6)
N2	0.0330 (5)	0.0344 (6)	0.0369 (6)	−0.0010 (5)	0.0064 (5)	−0.0004 (6)
C1	0.0309 (7)	0.0332 (7)	0.0409 (8)	0.0007 (6)	0.0032 (6)	−0.0052 (6)
C1M	0.0345 (7)	0.0499 (9)	0.0776 (12)	0.0069 (7)	−0.0013 (8)	−0.0076 (9)
C2	0.0299 (7)	0.0382 (8)	0.0381 (8)	−0.0007 (6)	0.0024 (6)	−0.0043 (6)
C11	0.0325 (7)	0.0324 (7)	0.0412 (8)	0.0019 (5)	0.0052 (6)	−0.0023 (7)
C12	0.0342 (7)	0.0476 (9)	0.0488 (9)	0.0002 (7)	0.0052 (7)	0.0011 (7)
C13	0.0412 (8)	0.0545 (10)	0.0609 (11)	−0.0071 (7)	0.0154 (8)	0.0018 (9)
C14	0.0619 (10)	0.0483 (9)	0.0536 (11)	−0.0012 (8)	0.0200 (9)	0.0084 (9)
C15	0.0618 (11)	0.0690 (12)	0.0559 (11)	0.0021 (10)	0.0019 (9)	0.0216 (10)
C16	0.0406 (8)	0.0610 (11)	0.0569 (11)	−0.0009 (8)	−0.0006 (7)	0.0140 (9)
C21	0.0317 (6)	0.0335 (7)	0.0352 (8)	0.0014 (5)	0.0025 (6)	−0.0045 (6)
C22	0.0319 (7)	0.0393 (8)	0.0395 (8)	0.0016 (6)	−0.0036 (6)	0.0011 (7)
C23	0.0272 (6)	0.0434 (8)	0.0426 (8)	−0.0019 (6)	−0.0012 (6)	0.0002 (7)
C24	0.0330 (6)	0.0325 (7)	0.0335 (7)	0.0010 (6)	0.0038 (6)	−0.0022 (6)
C25	0.0302 (7)	0.0424 (8)	0.0380 (8)	0.0058 (6)	−0.0010 (6)	−0.0005 (7)
C26	0.0253 (6)	0.0448 (8)	0.0405 (8)	0.0012 (6)	0.0019 (6)	−0.0027 (7)

Geometric parameters (Å, º)

O1—C1	1.2443 (15)	C12—H12	0.9500
O1M—C1M	1.4162 (17)	C13—C14	1.371 (2)
O1M—H1M	0.84 (2)	C13—H13	0.9500
O24—C24	1.3651 (17)	C14—C15	1.374 (2)
O24—H24	0.85 (2)	C14—H14	0.9500
N1—C1	1.3418 (18)	C15—C16	1.382 (2)
N1—N2	1.3863 (16)	C15—H15	0.9500
N1—H1	0.917 (16)	C16—H16	0.9500
N2—C2	1.2792 (18)	C21—C26	1.390 (2)
C1—C11	1.484 (2)	C21—C22	1.4035 (18)
C1M—H1M1	0.9800	C22—C23	1.374 (2)
C1M—H1M2	0.9800	C22—H22	0.9500
C1M—H1M3	0.9800	C23—C24	1.3895 (19)
C2—C21	1.455 (2)	C23—H23	0.9500
C2—H2	0.9500	C24—C25	1.3904 (18)
C11—C16	1.378 (2)	C25—C26	1.382 (2)
C11—C12	1.389 (2)	C25—H25	0.9500
C12—C13	1.387 (2)	C26—H26	0.9500
C1M—O1M—H1M	112.1 (14)	C13—C14—C15	119.47 (15)
C24—O24—H24	107.8 (14)	C13—C14—H14	120.3
C1—N1—N2	118.22 (11)	C15—C14—H14	120.3
C1—N1—H1	121.3 (10)	C14—C15—C16	119.99 (17)
N2—N1—H1	119.6 (10)	C14—C15—H15	120.0
C2—N2—N1	115.79 (11)	C16—C15—H15	120.0
O1—C1—N1	121.82 (13)	C11—C16—C15	121.12 (15)
O1—C1—C11	121.01 (13)	C11—C16—H16	119.4
N1—C1—C11	117.17 (11)	C15—C16—H16	119.4
O1M—C1M—H1M1	109.5	C26—C21—C22	117.79 (13)
O1M—C1M—H1M2	109.5	C26—C21—C2	120.12 (12)
H1M1—C1M—H1M2	109.5	C22—C21—C2	122.07 (13)
O1M—C1M—H1M3	109.5	C23—C22—C21	120.93 (13)
H1M1—C1M—H1M3	109.5	C23—C22—H22	119.5
H1M2—C1M—H1M3	109.5	C21—C22—H22	119.5
N2—C2—C21	121.20 (12)	C22—C23—C24	120.34 (12)
N2—C2—H2	119.4	C22—C23—H23	119.8
C21—C2—H2	119.4	C24—C23—H23	119.8
C16—C11—C12	118.72 (14)	O24—C24—C23	122.13 (11)
C16—C11—C1	118.07 (13)	O24—C24—C25	118.17 (13)
C12—C11—C1	123.19 (13)	C23—C24—C25	119.70 (13)
C13—C12—C11	119.77 (15)	C26—C25—C24	119.47 (13)
C13—C12—H12	120.1	C26—C25—H25	120.3
C11—C12—H12	120.1	C24—C25—H25	120.3
C14—C13—C12	120.92 (15)	C25—C26—C21	121.78 (12)
C14—C13—H13	119.5	C25—C26—H26	119.1
C12—C13—H13	119.5	C21—C26—H26	119.1
C1—N1—N2—C2	−178.83 (13)	C1—C11—C16—C15	178.63 (16)
N2—N1—C1—O1	3.8 (2)	C14—C15—C16—C11	−1.3 (3)
N2—N1—C1—C11	−176.51 (12)	N2—C2—C21—C26	−176.44 (13)
N1—N2—C2—C21	−176.79 (12)	N2—C2—C21—C22	5.0 (2)
O1—C1—C11—C16	−21.9 (2)	C26—C21—C22—C23	0.3 (2)
N1—C1—C11—C16	158.36 (14)	C2—C21—C22—C23	178.88 (13)
O1—C1—C11—C12	156.07 (14)	C21—C22—C23—C24	0.2 (2)
N1—C1—C11—C12	−23.7 (2)	C22—C23—C24—O24	179.78 (13)
C16—C11—C12—C13	0.5 (2)	C22—C23—C24—C25	−0.6 (2)
C1—C11—C12—C13	−177.52 (14)	O24—C24—C25—C26	−179.80 (13)
C11—C12—C13—C14	−0.7 (2)	C23—C24—C25—C26	0.6 (2)
C12—C13—C14—C15	0.0 (3)	C24—C25—C26—C21	−0.1 (2)
C13—C14—C15—C16	1.0 (3)	C22—C21—C26—C25	−0.3 (2)
C12—C11—C16—C15	0.6 (3)	C2—C21—C26—C25	−178.94 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1M^i	0.917 (16)	1.937 (16)	2.8424 (16)	168.9 (15)
O24—H24···O1^ii	0.85 (2)	1.97 (2)	2.7352 (14)	147.8 (19)
O24—H24···N2^ii	0.85 (2)	2.56 (2)	3.2742 (15)	141.2 (17)
O1M—H1M···O1	0.84 (2)	1.97 (2)	2.7803 (16)	160.8 (19)
C12—H12···O1M^i	0.95	2.60	3.310 (2)	132
C2—H2···O1M^i	0.95	2.65	3.3930 (18)	135
C22—H22···O24^iii	0.95	2.69	3.6348 (18)	174

Symmetry codes: (i) −x+1/2, y−1/2, z; (ii) −x, y−1/2, −z+3/2; (iii) −x, y+1/2, −z+3/2.

(VIII) 1-Benzoyl-2-(1,1-diphenylpropan-2-ylidene)hydrazone

Crystal data

C22H20N2O	Z = 4
Mr = 328.40	F(000) = 696
Monoclinic, P21/n	Dx = 1.219 Mg m^−3
a = 11.1869 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.9143 (6) Å	µ = 0.08 mm^−1
c = 20.233 (2) Å	T = 173 K
β = 92.967 (6)°	Block, colourless
V = 1789.0 (3) Å^3	0.59 × 0.56 × 0.55 mm

Data collection

Stoe IPDS II two-circle diffractometer	2918 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.051
Graphite monochromator	θmax = 26.8°, θmin = 2.0°
φ scans	h = −14→14
24782 measured reflections	k = −9→10
3783 independent reflections	l = −25→25

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.083	w = 1/[σ^2(Fo^2) + (0.045P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
3783 reflections	Δρmax = 0.16 e Å^−3
232 parameters	Δρmin = −0.13 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0221 (18)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.54851 (7)	0.93717 (9)	0.07609 (3)	0.0504 (2)
N1	0.59060 (8)	0.79043 (10)	−0.01401 (4)	0.0407 (2)
H1	0.5443 (11)	0.8645 (16)	−0.0366 (6)	0.051 (3)*
N2	0.66765 (7)	0.68251 (9)	−0.04488 (4)	0.03911 (19)
C1	0.60350 (9)	0.81931 (12)	0.05174 (5)	0.0397 (2)
C2	0.65429 (8)	0.66912 (11)	−0.10781 (4)	0.0379 (2)
C3	0.74267 (9)	0.55742 (12)	−0.14169 (4)	0.0393 (2)
H3	0.6956	0.4953	−0.1774	0.047*
C4	0.56275 (10)	0.75872 (14)	−0.15138 (5)	0.0499 (3)
H4A	0.4825	0.7232	−0.1400	0.075*
H4B	0.5748	0.7307	−0.1978	0.075*
H4C	0.5710	0.8810	−0.1450	0.075*
C11	0.68224 (9)	0.71025 (12)	0.09540 (5)	0.0413 (2)
C12	0.69355 (11)	0.53672 (14)	0.08684 (5)	0.0522 (3)
H12	0.6544	0.4823	0.0499	0.063*
C13	0.76257 (12)	0.44399 (17)	0.13273 (6)	0.0643 (3)
H13	0.7698	0.3252	0.1273	0.077*
C14	0.82061 (11)	0.52181 (19)	0.18582 (6)	0.0675 (4)
H14	0.8681	0.4570	0.2167	0.081*
C15	0.81011 (11)	0.69401 (19)	0.19444 (6)	0.0648 (3)
H15	0.8509	0.7480	0.2310	0.078*
C16	0.74000 (10)	0.78783 (15)	0.14964 (5)	0.0515 (3)
H16	0.7314	0.9060	0.1561	0.062*
C21	0.79889 (9)	0.42325 (12)	−0.09582 (5)	0.0413 (2)
C22	0.91982 (10)	0.41360 (14)	−0.07920 (5)	0.0500 (3)
H22	0.9729	0.4932	−0.0971	0.060*
C23	0.96469 (11)	0.28859 (15)	−0.03658 (6)	0.0605 (3)
H23	1.0482	0.2831	−0.0257	0.073*
C24	0.88924 (12)	0.17280 (14)	−0.01003 (6)	0.0606 (3)
H24	0.9201	0.0886	0.0197	0.073*
C25	0.76854 (12)	0.17993 (13)	−0.02683 (6)	0.0594 (3)
H25	0.7158	0.0999	−0.0089	0.071*
C26	0.72412 (11)	0.30297 (13)	−0.06959 (6)	0.0511 (3)
H26	0.6408	0.3057	−0.0814	0.061*
C31	0.83143 (9)	0.66808 (12)	−0.17633 (5)	0.0396 (2)
C32	0.88371 (10)	0.80801 (13)	−0.14544 (5)	0.0485 (3)
H32	0.8626	0.8376	−0.1021	0.058*
C33	0.96645 (10)	0.90526 (14)	−0.17718 (6)	0.0550 (3)
H33	1.0011	1.0016	−0.1557	0.066*
C34	0.99843 (10)	0.86216 (15)	−0.23999 (6)	0.0534 (3)
H34	1.0563	0.9273	−0.2614	0.064*
C35	0.94627 (10)	0.72460 (14)	−0.27141 (5)	0.0515 (3)
H35	0.9678	0.6951	−0.3147	0.062*
C36	0.86241 (9)	0.62911 (13)	−0.24003 (5)	0.0450 (2)
H36	0.8256	0.5357	−0.2624	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0591 (5)	0.0525 (4)	0.0404 (4)	0.0204 (3)	0.0095 (3)	0.0044 (3)
N1	0.0419 (4)	0.0424 (4)	0.0382 (4)	0.0098 (4)	0.0061 (3)	0.0044 (3)
N2	0.0383 (4)	0.0394 (4)	0.0401 (4)	0.0038 (3)	0.0062 (3)	0.0003 (3)
C1	0.0390 (5)	0.0418 (5)	0.0391 (5)	0.0035 (4)	0.0090 (4)	0.0056 (4)
C2	0.0379 (5)	0.0362 (5)	0.0398 (5)	−0.0032 (4)	0.0034 (4)	0.0011 (4)
C3	0.0401 (5)	0.0385 (5)	0.0394 (5)	−0.0026 (4)	0.0028 (4)	−0.0053 (4)
C4	0.0523 (6)	0.0550 (6)	0.0423 (5)	0.0086 (5)	0.0004 (4)	0.0019 (4)
C11	0.0385 (5)	0.0468 (5)	0.0394 (5)	0.0067 (4)	0.0091 (4)	0.0079 (4)
C12	0.0621 (7)	0.0481 (6)	0.0470 (5)	0.0101 (5)	0.0103 (5)	0.0081 (4)
C13	0.0726 (8)	0.0588 (7)	0.0629 (7)	0.0250 (6)	0.0183 (6)	0.0196 (6)
C14	0.0512 (7)	0.0897 (10)	0.0620 (7)	0.0239 (6)	0.0064 (6)	0.0284 (7)
C15	0.0498 (7)	0.0878 (9)	0.0559 (7)	0.0036 (6)	−0.0057 (5)	0.0111 (6)
C16	0.0474 (6)	0.0582 (6)	0.0489 (6)	0.0031 (5)	0.0015 (5)	0.0052 (5)
C21	0.0463 (5)	0.0361 (5)	0.0419 (5)	0.0015 (4)	0.0061 (4)	−0.0064 (4)
C22	0.0449 (6)	0.0482 (6)	0.0576 (6)	0.0041 (5)	0.0083 (5)	0.0015 (5)
C23	0.0534 (7)	0.0581 (7)	0.0699 (7)	0.0152 (5)	0.0028 (6)	0.0045 (6)
C24	0.0774 (8)	0.0423 (6)	0.0621 (7)	0.0152 (6)	0.0048 (6)	0.0040 (5)
C25	0.0740 (8)	0.0380 (5)	0.0668 (7)	−0.0041 (5)	0.0090 (6)	0.0044 (5)
C26	0.0524 (6)	0.0417 (5)	0.0592 (6)	−0.0058 (4)	0.0016 (5)	−0.0006 (4)
C31	0.0389 (5)	0.0412 (5)	0.0387 (5)	0.0037 (4)	0.0029 (4)	0.0006 (4)
C32	0.0516 (6)	0.0503 (6)	0.0442 (5)	−0.0069 (5)	0.0078 (4)	−0.0040 (4)
C33	0.0526 (6)	0.0502 (6)	0.0624 (7)	−0.0078 (5)	0.0053 (5)	0.0031 (5)
C34	0.0450 (6)	0.0566 (6)	0.0597 (6)	0.0069 (5)	0.0124 (5)	0.0199 (5)
C35	0.0517 (6)	0.0619 (6)	0.0417 (5)	0.0153 (5)	0.0104 (5)	0.0103 (5)
C36	0.0471 (5)	0.0484 (5)	0.0395 (5)	0.0083 (4)	0.0033 (4)	−0.0002 (4)

Geometric parameters (Å, º)

O1—C1	1.2340 (11)	C16—H16	0.9500
N1—C1	1.3502 (12)	C21—C22	1.3791 (15)
N1—N2	1.3850 (11)	C21—C26	1.3904 (14)
N1—H1	0.893 (13)	C22—C23	1.3892 (16)
N2—C2	1.2788 (12)	C22—H22	0.9500
C1—C11	1.4903 (13)	C23—C24	1.3739 (18)
C2—C4	1.4951 (14)	C23—H23	0.9500
C2—C3	1.5162 (13)	C24—C25	1.3763 (19)
C3—C31	1.5220 (13)	C24—H24	0.9500
C3—C21	1.5245 (13)	C25—C26	1.3782 (16)
C3—H3	1.0000	C25—H25	0.9500
C4—H4A	0.9800	C26—H26	0.9500
C4—H4B	0.9800	C31—C32	1.3861 (14)
C4—H4C	0.9800	C31—C36	1.3866 (13)
C11—C16	1.3876 (15)	C32—C33	1.3867 (15)
C11—C12	1.3908 (15)	C32—H32	0.9500
C12—C13	1.3866 (16)	C33—C34	1.3808 (16)
C12—H12	0.9500	C33—H33	0.9500
C13—C14	1.372 (2)	C34—C35	1.3753 (17)
C13—H13	0.9500	C34—H34	0.9500
C14—C15	1.380 (2)	C35—C36	1.3842 (15)
C14—H14	0.9500	C35—H35	0.9500
C15—C16	1.3836 (16)	C36—H36	0.9500
C15—H15	0.9500
C1—N1—N2	120.76 (8)	C15—C16—H16	119.8
C1—N1—H1	115.1 (7)	C11—C16—H16	119.8
N2—N1—H1	122.1 (7)	C22—C21—C26	118.09 (10)
C2—N2—N1	117.18 (8)	C22—C21—C3	123.75 (9)
O1—C1—N1	119.43 (9)	C26—C21—C3	118.16 (9)
O1—C1—C11	119.51 (8)	C21—C22—C23	120.61 (10)
N1—C1—C11	121.05 (8)	C21—C22—H22	119.7
N2—C2—C4	126.09 (9)	C23—C22—H22	119.7
N2—C2—C3	116.94 (8)	C24—C23—C22	120.54 (12)
C4—C2—C3	116.92 (8)	C24—C23—H23	119.7
C2—C3—C31	109.21 (7)	C22—C23—H23	119.7
C2—C3—C21	112.89 (7)	C23—C24—C25	119.39 (11)
C31—C3—C21	115.01 (8)	C23—C24—H24	120.3
C2—C3—H3	106.4	C25—C24—H24	120.3
C31—C3—H3	106.4	C24—C25—C26	120.08 (11)
C21—C3—H3	106.4	C24—C25—H25	120.0
C2—C4—H4A	109.5	C26—C25—H25	120.0
C2—C4—H4B	109.5	C25—C26—C21	121.26 (11)
H4A—C4—H4B	109.5	C25—C26—H26	119.4
C2—C4—H4C	109.5	C21—C26—H26	119.4
H4A—C4—H4C	109.5	C32—C31—C36	118.49 (9)
H4B—C4—H4C	109.5	C32—C31—C3	121.48 (8)
C16—C11—C12	119.60 (10)	C36—C31—C3	120.04 (9)
C16—C11—C1	116.70 (9)	C31—C32—C33	120.71 (10)
C12—C11—C1	123.56 (10)	C31—C32—H32	119.6
C13—C12—C11	119.36 (11)	C33—C32—H32	119.6
C13—C12—H12	120.3	C34—C33—C32	120.01 (11)
C11—C12—H12	120.3	C34—C33—H33	120.0
C14—C13—C12	120.74 (12)	C32—C33—H33	120.0
C14—C13—H13	119.6	C35—C34—C33	119.81 (10)
C12—C13—H13	119.6	C35—C34—H34	120.1
C13—C14—C15	120.16 (11)	C33—C34—H34	120.1
C13—C14—H14	119.9	C34—C35—C36	120.10 (10)
C15—C14—H14	119.9	C34—C35—H35	119.9
C14—C15—C16	119.76 (13)	C36—C35—H35	119.9
C14—C15—H15	120.1	C35—C36—C31	120.85 (10)
C16—C15—H15	120.1	C35—C36—H36	119.6
C15—C16—C11	120.37 (11)	C31—C36—H36	119.6
C1—N1—N2—C2	−175.98 (9)	C2—C3—C21—C26	62.41 (11)
N2—N1—C1—O1	167.14 (8)	C31—C3—C21—C26	−171.36 (9)
N2—N1—C1—C11	−13.38 (14)	C26—C21—C22—C23	−1.05 (15)
N1—N2—C2—C4	−0.24 (14)	C3—C21—C22—C23	179.43 (9)
N1—N2—C2—C3	177.12 (8)	C21—C22—C23—C24	−0.26 (17)
N2—C2—C3—C31	−104.90 (9)	C22—C23—C24—C25	1.00 (18)
C4—C2—C3—C31	72.72 (11)	C23—C24—C25—C26	−0.39 (18)
N2—C2—C3—C21	24.38 (11)	C24—C25—C26—C21	−0.95 (17)
C4—C2—C3—C21	−158.01 (8)	C22—C21—C26—C25	1.66 (15)
O1—C1—C11—C16	−33.23 (13)	C3—C21—C26—C25	−178.79 (9)
N1—C1—C11—C16	147.30 (9)	C2—C3—C31—C32	44.79 (12)
O1—C1—C11—C12	142.37 (10)	C21—C3—C31—C32	−83.32 (11)
N1—C1—C11—C12	−37.11 (14)	C2—C3—C31—C36	−135.73 (9)
C16—C11—C12—C13	−0.04 (16)	C21—C3—C31—C36	96.16 (11)
C1—C11—C12—C13	−175.51 (9)	C36—C31—C32—C33	−0.94 (16)
C11—C12—C13—C14	−0.74 (17)	C3—C31—C32—C33	178.54 (10)
C12—C13—C14—C15	0.49 (19)	C31—C32—C33—C34	−0.63 (17)
C13—C14—C15—C16	0.55 (19)	C32—C33—C34—C35	1.28 (17)
C14—C15—C16—C11	−1.33 (18)	C33—C34—C35—C36	−0.34 (16)
C12—C11—C16—C15	1.08 (16)	C34—C35—C36—C31	−1.27 (15)
C1—C11—C16—C15	176.85 (10)	C32—C31—C36—C35	1.89 (15)
C2—C3—C21—C22	−118.06 (10)	C3—C31—C36—C35	−177.60 (9)
C31—C3—C21—C22	8.17 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.893 (13)	2.023 (13)	2.9061 (11)	169.8 (11)
C4—H4C···O1^i	0.98	2.45	3.1399 (13)	127
C12—H12···N2	0.95	2.50	2.9048 (13)	106
C35—H35···O1^ii	0.95	2.65	3.5822 (13)	169

Symmetry codes: (i) −x+1, −y+2, −z; (ii) x+1/2, −y+3/2, z−1/2.