Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229614018658/eg3169sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229614018658/eg3169Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229614018658/eg3169IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229614018658/eg3169IIIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229614018658/eg3169IVsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229614018658/eg3169Vsup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229614018658/eg3169VIsup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229614018658/eg3169VIIsup8.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229614018658/eg3169VIIIsup9.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229614018658/eg3169sup10.pdf |
CCDC references: 1019653; 1019654; 1019655; 1019656; 1019657; 1019658; 1019659; 1019660
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.
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.
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 Uiso(H) = 1.5Ueq(C) for methyl or 1.2Ueq(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 Ueq(N) value it was also refined with Uiso(H1') = 1.2Ueq(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).
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).
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).
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) Å3 | 0.47 × 0.21 × 0.20 mm |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.089 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.94 | w = 1/[σ2(Fo2) + (0.062P)2] where P = (Fo2 + 2Fc2)/3 |
1929 reflections | (Δ/σ)max = 0.001 |
124 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C10H12N2O | V = 931.51 (15) Å3 |
Mr = 176.22 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.6950 (8) Å | µ = 0.08 mm−1 |
b = 17.129 (1) Å | T = 173 K |
c = 7.8316 (8) Å | 0.47 × 0.21 × 0.20 mm |
β = 115.525 (8)° |
Stoe IPDS II two-circle diffractometer | 1443 reflections with I > 2σ(I) |
18245 measured reflections | Rint = 0.056 |
1929 independent reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.089 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.94 | Δρmax = 0.15 e Å−3 |
1929 reflections | Δρmin = −0.26 e Å−3 |
124 parameters |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.868 (16) | 2.235 (16) | 3.0912 (14) | 169.0 (12) |
N1—H1···N2i | 0.868 (16) | 2.611 (15) | 3.1826 (14) | 124.4 (11) |
C3—H3C···O1i | 0.98 | 2.37 | 3.1238 (17) | 133 |
Symmetry code: (i) x, −y+3/2, z+1/2. |
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) Å3 | 0.54 × 0.36 × 0.24 mm |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | w = 1/[σ2(Fo2) + (0.067P)2] where P = (Fo2 + 2Fc2)/3 |
2589 reflections | (Δ/σ)max < 0.001 |
168 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C15H20N2O | V = 1350.4 (2) Å3 |
Mr = 244.33 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.3086 (9) Å | µ = 0.08 mm−1 |
b = 18.283 (2) Å | T = 173 K |
c = 8.1543 (7) Å | 0.54 × 0.36 × 0.24 mm |
β = 103.328 (7)° |
Stoe IPDS II two-circle diffractometer | 1909 reflections with I > 2σ(I) |
18518 measured reflections | Rint = 0.105 |
2589 independent reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.109 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | Δρmax = 0.30 e Å−3 |
2589 reflections | Δρmin = −0.19 e Å−3 |
168 parameters |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.847 (17) | 2.191 (18) | 3.0213 (16) | 166.6 (14) |
C3—H3C···O1i | 0.98 | 2.60 | 3.0589 (18) | 109 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
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) Å3 | 0.53 × 0.26 × 0.21 mm |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.080 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.85 | w = 1/[σ2(Fo2) + (0.044P)2] where P = (Fo2 + 2Fc2)/3 |
2754 reflections | (Δ/σ)max < 0.001 |
204 parameters | Δρmax = 0.11 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
C19H16N2O | V = 1420.6 (2) Å3 |
Mr = 288.34 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 5.5789 (5) Å | µ = 0.09 mm−1 |
b = 7.6868 (9) Å | T = 173 K |
c = 33.128 (3) Å | 0.53 × 0.26 × 0.21 mm |
β = 90.356 (7)° |
Stoe IPDS II two-circle diffractometer | 1715 reflections with I > 2σ(I) |
19261 measured reflections | Rint = 0.061 |
2754 independent reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.080 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.85 | Δρmax = 0.11 e Å−3 |
2754 reflections | Δρmin = −0.14 e Å−3 |
204 parameters |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.885 (17) | 2.643 (18) | 3.5134 (18) | 168.1 (15) |
C3—H3C···O1i | 0.98 | 2.61 | 3.2256 (18) | 121 |
C25—H25···O1ii | 0.95 | 2.60 | 3.378 (2) | 139 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z. |
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) Å3 | 0.54 × 0.52 × 0.50 mm |
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 on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.098 | w = 1/[σ2(Fo2) + (0.055P)2] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0023 (4) |
C20H22N2O | V = 3361.7 (5) Å3 |
Mr = 306.40 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 16.0939 (15) Å | µ = 0.08 mm−1 |
b = 13.8666 (8) Å | T = 173 K |
c = 16.8556 (16) Å | 0.54 × 0.52 × 0.50 mm |
β = 116.661 (7)° |
Stoe IPDS II two-circle diffractometer | 3004 reflections with I > 2σ(I) |
27068 measured reflections | Rint = 0.069 |
3956 independent reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.27 e Å−3 |
3956 reflections | Δρmin = −0.16 e Å−3 |
213 parameters |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O1i | 0.95 | 2.60 | 3.1911 (14) | 121 |
C15—H15···O1i | 0.95 | 2.54 | 3.1644 (13) | 123 |
C26—H26···O1ii | 0.95 | 2.45 | 3.2940 (14) | 147 |
C23—H23···O1iii | 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. |
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) Å3 | 0.40 × 0.40 × 0.30 mm |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.072 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.81 | w = 1/[σ2(Fo2) + (0.030P)2] where P = (Fo2 + 2Fc2)/3 |
6006 reflections | (Δ/σ)max = 0.001 |
423 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C20H16N2O | V = 3134.3 (5) Å3 |
Mr = 300.35 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 16.863 (1) Å | µ = 0.08 mm−1 |
b = 10.1678 (8) Å | T = 173 K |
c = 18.694 (2) Å | 0.40 × 0.40 × 0.30 mm |
β = 102.079 (6)° |
Stoe IPDS II two-circle diffractometer | 3934 reflections with I > 2σ(I) |
42459 measured reflections | Rint = 0.104 |
6006 independent reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.072 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.81 | Δρmax = 0.14 e Å−3 |
6006 reflections | Δρmin = −0.15 e Å−3 |
423 parameters |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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···O1i | 0.95 | 2.58 | 3.5238 (18) | 171 |
Symmetry code: (i) −x+1, −y+2, −z. |
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) Å3 | 0.56 × 0.48 × 0.31 mm |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.064 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.81 | w = 1/[σ2(Fo2) + (0.030P)2] where P = (Fo2 + 2Fc2)/3 |
6453 reflections | (Δ/σ)max = 0.001 |
441 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C20H15ClN2O | V = 3308.1 (12) Å3 |
Mr = 334.79 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 19.432 (4) Å | µ = 0.24 mm−1 |
b = 8.9330 (18) Å | T = 173 K |
c = 19.496 (4) Å | 0.56 × 0.48 × 0.31 mm |
β = 102.18 (3)° |
Stoe IPDS II two-circle diffractometer | 4590 reflections with I > 2σ(I) |
46062 measured reflections | Rint = 0.074 |
6453 independent reflections |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.064 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.81 | Δρmax = 0.30 e Å−3 |
6453 reflections | Δρmin = −0.27 e Å−3 |
441 parameters |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
D—H···A | D—H | H···A | D···A | D—H···A |
C26—H26···O1i | 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′···O1iv | 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. |
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) Å3 | 0.53 × 0.32 × 0.24 mm |
Z = 8 |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.073 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.80 | w = 1/[σ2(Fo2) + (0.040P)2] where P = (Fo2 + 2Fc2)/3 |
2745 reflections | (Δ/σ)max = 0.001 |
194 parameters | Δρmax = 0.11 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
C15H16N2O3 | V = 2746.6 (4) Å3 |
Mr = 272.30 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 13.382 (1) Å | µ = 0.09 mm−1 |
b = 8.8183 (8) Å | T = 173 K |
c = 23.275 (2) Å | 0.53 × 0.32 × 0.24 mm |
Stoe IPDS II two-circle diffractometer | 1723 reflections with I > 2σ(I) |
33745 measured reflections | Rint = 0.083 |
2745 independent reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.073 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.80 | Δρmax = 0.11 e Å−3 |
2745 reflections | Δρmin = −0.14 e Å−3 |
194 parameters |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1Mi | 0.917 (16) | 1.937 (16) | 2.8424 (16) | 168.9 (15) |
O24—H24···O1ii | 0.85 (2) | 1.97 (2) | 2.7352 (14) | 147.8 (19) |
O24—H24···N2ii | 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···O1Mi | 0.95 | 2.60 | 3.310 (2) | 132 |
C2—H2···O1Mi | 0.95 | 2.65 | 3.3930 (18) | 135 |
C22—H22···O24iii | 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. |
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) Å3 | 0.59 × 0.56 × 0.55 mm |
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 on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.030 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.083 | w = 1/[σ2(Fo2) + (0.045P)2] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0221 (18) |
C22H20N2O | V = 1789.0 (3) Å3 |
Mr = 328.40 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.1869 (8) Å | µ = 0.08 mm−1 |
b = 7.9143 (6) Å | T = 173 K |
c = 20.233 (2) Å | 0.59 × 0.56 × 0.55 mm |
β = 92.967 (6)° |
Stoe IPDS II two-circle diffractometer | 2918 reflections with I > 2σ(I) |
24782 measured reflections | Rint = 0.051 |
3783 independent reflections |
R[F2 > 2σ(F2)] = 0.030 | 0 restraints |
wR(F2) = 0.083 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.16 e Å−3 |
3783 reflections | Δρmin = −0.13 e Å−3 |
232 parameters |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.893 (13) | 2.023 (13) | 2.9061 (11) | 169.8 (11) |
C4—H4C···O1i | 0.98 | 2.45 | 3.1399 (13) | 127 |
C12—H12···N2 | 0.95 | 2.50 | 2.9048 (13) | 106 |
C35—H35···O1ii | 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. |
Experimental details
(I) | (II) | (III) | (IV) | |
Crystal data | ||||
Chemical formula | C10H12N2O | C15H20N2O | C19H16N2O | C20H22N2O |
Mr | 176.22 | 244.33 | 288.34 | 306.40 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21/n | Monoclinic, C2/c |
Temperature (K) | 173 | 173 | 173 | 173 |
a, b, c (Å) | 7.6950 (8), 17.129 (1), 7.8316 (8) | 9.3086 (9), 18.283 (2), 8.1543 (7) | 5.5789 (5), 7.6868 (9), 33.128 (3) | 16.0939 (15), 13.8666 (8), 16.8556 (16) |
α, β, γ (°) | 90, 115.525 (8), 90 | 90, 103.328 (7), 90 | 90, 90.356 (7), 90 | 90, 116.661 (7), 90 |
V (Å3) | 931.51 (15) | 1350.4 (2) | 1420.6 (2) | 3361.7 (5) |
Z | 4 | 4 | 4 | 8 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.08 | 0.08 | 0.09 | 0.08 |
Crystal size (mm) | 0.47 × 0.21 × 0.20 | 0.54 × 0.36 × 0.24 | 0.53 × 0.26 × 0.21 | 0.54 × 0.52 × 0.50 |
Data collection | ||||
Diffractometer | Stoe IPDS II two-circle diffractometer | Stoe IPDS II two-circle diffractometer | Stoe IPDS II two-circle diffractometer | Stoe IPDS II two-circle diffractometer |
Absorption correction | – | – | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18245, 1929, 1443 | 18518, 2589, 1909 | 19261, 2754, 1715 | 27068, 3956, 3004 |
Rint | 0.056 | 0.105 | 0.061 | 0.069 |
(sin θ/λ)max (Å−1) | 0.629 | 0.614 | 0.614 | 0.657 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.089, 0.94 | 0.040, 0.109, 0.97 | 0.033, 0.080, 0.85 | 0.036, 0.098, 1.06 |
No. of reflections | 1929 | 2589 | 2754 | 3956 |
No. of parameters | 124 | 168 | 204 | 213 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.15, −0.26 | 0.30, −0.19 | 0.11, −0.14 | 0.27, −0.16 |
(V) | (VI) | (VII) | (VIII) | |
Crystal data | ||||
Chemical formula | C20H16N2O | C20H15ClN2O | C15H16N2O3 | C22H20N2O |
Mr | 300.35 | 334.79 | 272.30 | 328.40 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/n | Orthorhombic, Pbca | Monoclinic, P21/n |
Temperature (K) | 173 | 173 | 173 | 173 |
a, b, c (Å) | 16.863 (1), 10.1678 (8), 18.694 (2) | 19.432 (4), 8.9330 (18), 19.496 (4) | 13.382 (1), 8.8183 (8), 23.275 (2) | 11.1869 (8), 7.9143 (6), 20.233 (2) |
α, β, γ (°) | 90, 102.079 (6), 90 | 90, 102.18 (3), 90 | 90, 90, 90 | 90, 92.967 (6), 90 |
V (Å3) | 3134.3 (5) | 3308.1 (12) | 2746.6 (4) | 1789.0 (3) |
Z | 8 | 8 | 8 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.08 | 0.24 | 0.09 | 0.08 |
Crystal size (mm) | 0.40 × 0.40 × 0.30 | 0.56 × 0.48 × 0.31 | 0.53 × 0.32 × 0.24 | 0.59 × 0.56 × 0.55 |
Data collection | ||||
Diffractometer | Stoe IPDS II two-circle diffractometer | Stoe IPDS II two-circle diffractometer | Stoe IPDS II two-circle diffractometer | Stoe IPDS II two-circle diffractometer |
Absorption correction | – | – | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 42459, 6006, 3934 | 46062, 6453, 4590 | 33745, 2745, 1723 | 24782, 3783, 2918 |
Rint | 0.104 | 0.074 | 0.083 | 0.051 |
(sin θ/λ)max (Å−1) | 0.614 | 0.617 | 0.622 | 0.633 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.072, 0.81 | 0.031, 0.064, 0.81 | 0.032, 0.073, 0.80 | 0.030, 0.083, 1.10 |
No. of reflections | 6006 | 6453 | 2745 | 3783 |
No. of parameters | 423 | 441 | 194 | 232 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.14, −0.15 | 0.30, −0.27 | 0.11, −0.14 | 0.16, −0.13 |
Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008) and XP in SHELXTL-Plus (Sheldrick, 2008), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.868 (16) | 2.235 (16) | 3.0912 (14) | 169.0 (12) |
N1—H1···N2i | 0.868 (16) | 2.611 (15) | 3.1826 (14) | 124.4 (11) |
C3—H3C···O1i | 0.98 | 2.37 | 3.1238 (17) | 132.9 |
Symmetry code: (i) x, −y+3/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.847 (17) | 2.191 (18) | 3.0213 (16) | 166.6 (14) |
C3—H3C···O1i | 0.98 | 2.60 | 3.0589 (18) | 108.8 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.885 (17) | 2.643 (18) | 3.5134 (18) | 168.1 (15) |
C3—H3C···O1i | 0.98 | 2.61 | 3.2256 (18) | 121.0 |
C25—H25···O1ii | 0.95 | 2.60 | 3.378 (2) | 139.3 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O1i | 0.95 | 2.60 | 3.1911 (14) | 120.5 |
C15—H15···O1i | 0.95 | 2.54 | 3.1644 (13) | 123.0 |
C26—H26···O1ii | 0.95 | 2.45 | 3.2940 (14) | 147.3 |
C23—H23···O1iii | 0.95 | 2.60 | 3.3266 (15) | 133.1 |
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. |
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) | 110.7 |
C34—H34···O1i | 0.95 | 2.58 | 3.5238 (18) | 170.8 |
Symmetry code: (i) −x+1, −y+2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C26—H26···O1i | 0.95 | 2.45 | 3.344 (3) | 156.4 |
C36—H36···O1'ii | 0.95 | 2.48 | 3.085 (2) | 121.7 |
C26'—H26'···O1'iii | 0.95 | 2.40 | 3.261 (2) | 151.2 |
C23'—H23'···O1iv | 0.95 | 2.44 | 3.320 (3) | 154.7 |
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. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1Mi | 0.917 (16) | 1.937 (16) | 2.8424 (16) | 168.9 (15) |
O24—H24···O1ii | 0.85 (2) | 1.97 (2) | 2.7352 (14) | 147.8 (19) |
O24—H24···N2ii | 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···O1Mi | 0.95 | 2.60 | 3.310 (2) | 132.3 |
C2—H2···O1Mi | 0.95 | 2.65 | 3.3930 (18) | 135.4 |
C22—H22···O24iii | 0.95 | 2.69 | 3.6348 (18) | 173.9 |
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. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.893 (13) | 2.023 (13) | 2.9061 (11) | 169.8 (11) |
C4—H4C···O1i | 0.98 | 2.45 | 3.1399 (13) | 127.3 |
C12—H12···N2 | 0.95 | 2.50 | 2.9048 (13) | 105.8 |
C35—H35···O1ii | 0.95 | 2.65 | 3.5822 (13) | 169.0 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) x+1/2, −y+3/2, z−1/2. |