Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113016119/eg3127sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113016119/eg3127Isup2.hkl |
CCDC reference: 843226
The versatile properties of compounds containing the benzimidazole system have recently received much attention. Studies of the crystal structures and spectroscopic properties of benzimidazole-containing compounds are also common (Małecki, 2010; Wu et al., 2012; Abdel Ghani & Mansour, 2012). This is related to the wide range of biological and pharmacological activities of these compounds, including antihelmentic, antiviral, antitumour, antimicrobial and antihistaminic effects. Benzimidazole derivatives, their salts, and complexes involving them as ligands, are currently being studied (Małecki, 2010; Wu et al., 2012). Because these compounds exhibit anticancer activity, DNA-binding research, including theoretical and quantum-mechanical studies, on new complexes containing benzimidazole fragments is common (Li et al., 2006; Fan et al., 2011; Shang et al., 2011) and may lead to the development of a new generation of antitumour drugs.
There is another application of benzimidazole-containing substances, in that compounds with benzimidazole fragments have good growth-regulating properties (Collins et al., 1963; Ward et al., 1986; Kołodziej et al., 2006). It is well known that benzimidazole fragments are steric analogues of the purine fragments of natural phytohormones which have cytokinin activity, including zeatin, N6-(Δ2-isopentyl)adenine and 6-(3-methylbut-2-enylamino)purine. We synthesized a series of heterocycles with benzimidazole or benzoxazole fragments fused with the pyrrolidone group (Grinev et al., 2010). The growth-regulating activity of these compounds was demonstrated with wheat seeds, and one member of the series showed an activity up to 23% higher than 3-indoleacetic acid under similar conditions (Grinev et al., 2011). Thus, 3a-phenyl-2,3,3a,4-tetrahydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-1-one, (I), was expected to be the most promising growth promoter. Compound (I) has already been described and structurally characterized at ambient temperature by Chimirri et al. (1984). The study of the steric structure of (I) may provide a key to understanding the mechanics of the molecular processes of plant growth, which is very important for the development of new growth-stimulating agricultural products.
Compound (I) [Fig. 1; this structure has been deposited with the Cambridge Structural Database (Allen, 2002), deposition number CCDC 843226] crystallizes with Z = 2 in the space group P1. The partly saturated benzimidazole fragment is almost flat, and the saturated imidazole ring is fixed in the envelope conformation [torsion angle N1—C5—C10—N2 = 2.08 (10)°]. The N1—C5, N2—C10, N1—C4 and N2—C4 bonds are longer than those in similar structures (V)–(IX) (Cortés et al., 2011; Walczak et al., 2008; Nicoló et al., 2001; Qi et al., 2009; Abdel Ghani & Mansour, 2012), in which the imidazole systems are unsaturated, and are close to those in structures (III) and (IV) (Hazelton et al., 1995; Kaftory et al., 2002; Rivera et al., 2011), where the imidazole systems are completely saturated (see Scheme 2 and Table 2). The structure closest to (I) is that of (II) (Scheme 2; Sillanpää et al., 1995). The N1—C5, N2—C10, N1—C4 and N2—C4 bond lengths of (I) and (II) are very close to one another, but there are some differences in the benzimidazole regions between structures (I) and (II). Specifically, the C5—C10, C9—C8 and C7—C6 bonds in (I) are significantly longer than the same bonds in the benzene rings of (II), and the C10—C9, C8—C7 and C6—C5 bond lengths in both (I) and (II). These differences in bond lengths and, therefore, orders of bonds lead to a distortion of the aromatic system, and this fact may explain the peculiarities of the chemical behaviour of (I) in electrophilic substitution reactions. As shown before, SE reactions are directed mostly to the seventh position (atom C8 in Fig. 1) of this heterocyclic system (Grinev & Egorova, 2011). In (II), all bonds of the benzene ring are of similar length (about 1.38 Å), except for C8—C7, which is about 0.03 Å shorter. The C9—C8 and C7–C6 bond lengths in (I) are very close to those in (IV), and the C5—C10 bond length in (I) is similar to that in (VII).
The pyrrolidone ring of (I) is nonplanar and is in a distorted envelope conformation. Atom C4 is displaced from the plane, with torsion angles C4—N2—C10—C5 = 9.53 (9)° and C5—N1—C4—N2 = 17.45 (9)°. The pyrrolidone fragments in (I) and (II) are also similar. The C1—C2—C3—C4 torsion angle in (I) [33.88 (9)°] is very close to that in (II) [38.6 (3)°]. The relevant bond lengths of this fragment in (I) and (II) are not significantly different, except for the N2—C1 bond, which is about 0.02 Å shorter in (II) than in (I), and they are typical of other pyrrolidone-containing compounds (Derricott, 1980; Soriano-García et al., 1986; Müller et al., 1996; Hollenberg et al., 1997; Wang et al., 2006; Herler et al., 2007) (see Table 3).
The phenyl ring in the 3a position (atom C4 in Fig. 1) of (I) is located in such a way that the plane of the benzene ring and the C4—N2 bond are almost coplanar [torsion angles N2—C4—C11—C16 = -3.03 (12)° and N2—C4—C11—C12 = 179.85 (8)°], in contrast with (II), in which the corresponding angles are -29.2 (4) and 155.0 (3)°.
In the structure of (I), there are intermolecular N—H···O hydrogen bonds between the secondary amino group of one molecule and the carbonyl group of another molecule, with an H···O distance of 2.112 (17) Å. The molecules are linked into one-dimensional chains by these hydrogen bonds. The hydrogen bonds in (II) have the same parameters.
The hydrogen-bonded chains in (I) are weakly linked by aromatic parallel displaced π–π stacking interactions to form a three-dimensional structure [interplanar distance = 3.521 (9) Å, centroid-to-centroid separation = 4.26 (2) Å, ring offset = 2.39 (2) Å, angle θ = 34.21 (2)° and angle γ = 180°] (Fig. 2 and Scheme 4). According to the Hunter and Sanders diagram (Hunter & Sanders, 1990; Hunter et al., 2001), these parameters correspond to the `attraction' zone, and thus sandwich-type π–π stacking interactions are observed.
The structures in Scheme 3 and Table 3 are not discussed anywhere. Please supply text to put them in context.
For the preparation of 3a-phenyl-2,3,3a,4-tetrahydro-1H-benzo[d]-pyrrolo[1,2-a]imidazol-1-one, a solution of 4-oxo-4-phenylbutanoic acid (2 g, 11 mmol) and 1,2-phenylenediamine (1.2 g, 11 mmol) in anhydrous benzene (30 ml) was boiled while continuously distilling off the azeotropic mixture with formed water over a period of 5 h. After standing overnight, the separated crystals or precipitate were washed with benzene and then with n-hexane. If necessary, it may be recrystallized from acetone (yield 2.12 g, 75%; light-yellow crystals; m.p. 429–432 K). IR spectrum (KBr pellets, ν, cm-1): 3330 (NH), 1710 (C═O, Amide I), 1320 (C—N). 1H NMR (CDCl3, δ, p.p.m.): 2.35–2.60 (m, 2H, C3H2 pyrrolidine), 2.70–2.90 (m, 2H, C2H2 pyrrolidine), 4.38 (s, 1H, NH), 6.50–6.90 (m, 4H, aromatic), 7.25–7.60 (m, 5H, aromatic, Ph). Analysis, found (%): C 76.56, H 5.73, N 11.56; calculated for C16H14N2O: C 76.80, H 5.60, N 11.20.
A suitable single crystal of (I) (0.23 × 0.20 × 0.19 mm) was obtained by slowly cooling the reaction mixture to ambient temperature. This crystal was washed with benzene and then with n-hexane and finally dried in a vacuum (without any recrystallization in this case).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C16H14N2O | Z = 2 |
Mr = 250.29 | F(000) = 264 |
Triclinic, P1 | Dx = 1.324 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.2966 (9) Å | Cell parameters from 354 reflections |
b = 9.1081 (11) Å | θ = 3–29° |
c = 10.3723 (12) Å | µ = 0.08 mm−1 |
α = 66.803 (1)° | T = 100 K |
β = 88.947 (2)° | Prism, colourless |
γ = 82.509 (2)° | 0.23 × 0.20 × 0.19 mm |
V = 627.78 (13) Å3 |
Bruker SMART 1000 CCD area-detector diffractometer | 3492 independent reflections |
Radiation source: fine-focus sealed tube | 3259 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
ϕ and ω scans | θmax = 29.6°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) | h = −10→10 |
Tmin = 0.981, Tmax = 0.984 | k = −12→12 |
7155 measured reflections | l = −14→14 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0792P)2 + 0.230P] where P = (Fo2 + 2Fc2)/3 |
3492 reflections | (Δ/σ)max < 0.001 |
176 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.41 e Å−3 |
C16H14N2O | γ = 82.509 (2)° |
Mr = 250.29 | V = 627.78 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.2966 (9) Å | Mo Kα radiation |
b = 9.1081 (11) Å | µ = 0.08 mm−1 |
c = 10.3723 (12) Å | T = 100 K |
α = 66.803 (1)° | 0.23 × 0.20 × 0.19 mm |
β = 88.947 (2)° |
Bruker SMART 1000 CCD area-detector diffractometer | 3492 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) | 3259 reflections with I > 2σ(I) |
Tmin = 0.981, Tmax = 0.984 | Rint = 0.016 |
7155 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.125 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.48 e Å−3 |
3492 reflections | Δρmin = −0.41 e Å−3 |
176 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.61829 (11) | 0.02564 (9) | 0.61171 (8) | 0.01383 (17) | |
H1N | 0.493 (2) | 0.0435 (19) | 0.6207 (17) | 0.030 (4)* | |
N2 | 0.90402 (10) | 0.01688 (9) | 0.70692 (8) | 0.01328 (16) | |
O1 | 1.21712 (9) | 0.01286 (9) | 0.67719 (8) | 0.01995 (17) | |
C1 | 1.06087 (12) | 0.08609 (11) | 0.65663 (9) | 0.01507 (18) | |
C2 | 0.99897 (13) | 0.26406 (11) | 0.57228 (10) | 0.01707 (19) | |
H2A | 1.0777 | 0.3076 | 0.4907 | 0.020* | |
H2B | 1.0020 | 0.3270 | 0.6311 | 0.020* | |
C3 | 0.79979 (12) | 0.26642 (11) | 0.52490 (10) | 0.01545 (18) | |
H3A | 0.7976 | 0.2467 | 0.4377 | 0.019* | |
H3B | 0.7237 | 0.3707 | 0.5092 | 0.019* | |
C4 | 0.73073 (12) | 0.12709 (10) | 0.64971 (9) | 0.01247 (17) | |
C5 | 0.69624 (12) | −0.13486 (10) | 0.68207 (9) | 0.01322 (18) | |
C6 | 0.62667 (13) | −0.27503 (11) | 0.69730 (10) | 0.01614 (19) | |
H6A | 0.5072 | −0.2713 | 0.6603 | 0.019* | |
C7 | 0.73790 (13) | −0.42250 (11) | 0.76887 (10) | 0.01738 (19) | |
H7A | 0.6929 | −0.5199 | 0.7800 | 0.021* | |
C8 | 0.91289 (13) | −0.42918 (11) | 0.82398 (10) | 0.01699 (19) | |
H8A | 0.9852 | −0.5308 | 0.8720 | 0.020* | |
C9 | 0.98365 (12) | −0.28751 (11) | 0.80946 (10) | 0.01587 (19) | |
H9A | 1.1027 | −0.2908 | 0.8468 | 0.019* | |
C10 | 0.87283 (12) | −0.14334 (10) | 0.73858 (9) | 0.01316 (18) | |
C11 | 0.63184 (12) | 0.18362 (10) | 0.75601 (9) | 0.01345 (18) | |
C12 | 0.46662 (13) | 0.28868 (12) | 0.71129 (10) | 0.01736 (19) | |
H12A | 0.4231 | 0.3254 | 0.6166 | 0.021* | |
C13 | 0.36550 (14) | 0.33989 (13) | 0.80441 (11) | 0.0213 (2) | |
H13A | 0.2537 | 0.4118 | 0.7730 | 0.026* | |
C14 | 0.42789 (15) | 0.28592 (13) | 0.94374 (11) | 0.0215 (2) | |
H14A | 0.3586 | 0.3206 | 1.0074 | 0.026* | |
C15 | 0.59126 (15) | 0.18152 (12) | 0.98899 (10) | 0.0204 (2) | |
H15A | 0.6339 | 0.1445 | 1.0839 | 0.025* | |
C16 | 0.69403 (13) | 0.13019 (11) | 0.89523 (10) | 0.01684 (19) | |
H16A | 0.8062 | 0.0589 | 0.9267 | 0.020* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0106 (3) | 0.0138 (3) | 0.0176 (4) | −0.0009 (3) | −0.0015 (3) | −0.0068 (3) |
N2 | 0.0096 (3) | 0.0129 (3) | 0.0166 (3) | −0.0005 (3) | −0.0001 (3) | −0.0053 (3) |
O1 | 0.0106 (3) | 0.0230 (4) | 0.0245 (4) | −0.0015 (3) | 0.0006 (3) | −0.0078 (3) |
C1 | 0.0126 (4) | 0.0176 (4) | 0.0160 (4) | −0.0034 (3) | 0.0009 (3) | −0.0073 (3) |
C2 | 0.0137 (4) | 0.0165 (4) | 0.0201 (4) | −0.0039 (3) | 0.0014 (3) | −0.0057 (3) |
C3 | 0.0128 (4) | 0.0158 (4) | 0.0154 (4) | −0.0016 (3) | 0.0012 (3) | −0.0038 (3) |
C4 | 0.0096 (4) | 0.0136 (4) | 0.0137 (4) | −0.0008 (3) | −0.0001 (3) | −0.0050 (3) |
C5 | 0.0126 (4) | 0.0140 (4) | 0.0129 (4) | −0.0008 (3) | 0.0011 (3) | −0.0054 (3) |
C6 | 0.0151 (4) | 0.0169 (4) | 0.0172 (4) | −0.0039 (3) | 0.0008 (3) | −0.0069 (3) |
C7 | 0.0200 (4) | 0.0146 (4) | 0.0178 (4) | −0.0036 (3) | 0.0036 (3) | −0.0065 (3) |
C8 | 0.0176 (4) | 0.0141 (4) | 0.0169 (4) | 0.0001 (3) | 0.0032 (3) | −0.0044 (3) |
C9 | 0.0130 (4) | 0.0167 (4) | 0.0159 (4) | −0.0002 (3) | 0.0014 (3) | −0.0049 (3) |
C10 | 0.0118 (4) | 0.0137 (4) | 0.0140 (4) | −0.0019 (3) | 0.0016 (3) | −0.0054 (3) |
C11 | 0.0123 (4) | 0.0136 (4) | 0.0153 (4) | −0.0027 (3) | 0.0020 (3) | −0.0063 (3) |
C12 | 0.0141 (4) | 0.0201 (4) | 0.0185 (4) | 0.0003 (3) | 0.0002 (3) | −0.0089 (3) |
C13 | 0.0158 (4) | 0.0240 (5) | 0.0263 (5) | −0.0002 (3) | 0.0040 (3) | −0.0131 (4) |
C14 | 0.0220 (5) | 0.0239 (5) | 0.0227 (5) | −0.0060 (4) | 0.0089 (4) | −0.0129 (4) |
C15 | 0.0248 (5) | 0.0215 (4) | 0.0159 (4) | −0.0064 (4) | 0.0036 (3) | −0.0074 (4) |
C16 | 0.0175 (4) | 0.0161 (4) | 0.0160 (4) | −0.0025 (3) | 0.0006 (3) | −0.0053 (3) |
N1—C5 | 1.3968 (11) | C6—H6A | 0.9500 |
N1—C4 | 1.4761 (11) | C7—C8 | 1.3928 (13) |
N1—H1N | 0.914 (16) | C7—H7A | 0.9500 |
N2—C1 | 1.3735 (11) | C8—C9 | 1.4043 (13) |
N2—C10 | 1.4126 (11) | C8—H8A | 0.9500 |
N2—C4 | 1.4785 (11) | C9—C10 | 1.3795 (12) |
O1—C1 | 1.2201 (11) | C9—H9A | 0.9500 |
C1—C2 | 1.5177 (13) | C11—C16 | 1.3932 (13) |
C2—C3 | 1.5375 (13) | C11—C12 | 1.3979 (12) |
C2—H2A | 0.9900 | C12—C13 | 1.3907 (13) |
C2—H2B | 0.9900 | C12—H12A | 0.9500 |
C3—C4 | 1.5456 (12) | C13—C14 | 1.3941 (15) |
C3—H3A | 0.9900 | C13—H13A | 0.9500 |
C3—H3B | 0.9900 | C14—C15 | 1.3853 (15) |
C4—C11 | 1.5240 (12) | C14—H14A | 0.9500 |
C5—C6 | 1.3855 (12) | C15—C16 | 1.4023 (13) |
C5—C10 | 1.4057 (12) | C15—H15A | 0.9500 |
C6—C7 | 1.4022 (13) | C16—H16A | 0.9500 |
C5—N1—C4 | 107.81 (7) | C7—C6—H6A | 121.0 |
C5—N1—H1N | 114.1 (10) | C8—C7—C6 | 121.42 (9) |
C4—N1—H1N | 116.3 (10) | C8—C7—H7A | 119.3 |
C1—N2—C10 | 128.12 (8) | C6—C7—H7A | 119.3 |
C1—N2—C4 | 113.60 (7) | C7—C8—C9 | 120.80 (8) |
C10—N2—C4 | 109.45 (7) | C7—C8—H8A | 119.6 |
O1—C1—N2 | 124.57 (9) | C9—C8—H8A | 119.6 |
O1—C1—C2 | 128.65 (8) | C10—C9—C8 | 117.14 (8) |
N2—C1—C2 | 106.78 (7) | C10—C9—H9A | 121.4 |
C1—C2—C3 | 102.85 (7) | C8—C9—H9A | 121.4 |
C1—C2—H2A | 111.2 | C9—C10—C5 | 122.64 (8) |
C3—C2—H2A | 111.2 | C9—C10—N2 | 130.60 (8) |
C1—C2—H2B | 111.2 | C5—C10—N2 | 106.76 (7) |
C3—C2—H2B | 111.2 | C16—C11—C12 | 119.26 (8) |
H2A—C2—H2B | 109.1 | C16—C11—C4 | 123.18 (8) |
C2—C3—C4 | 103.00 (7) | C12—C11—C4 | 117.49 (8) |
C2—C3—H3A | 111.2 | C13—C12—C11 | 120.48 (9) |
C4—C3—H3A | 111.2 | C13—C12—H12A | 119.8 |
C2—C3—H3B | 111.2 | C11—C12—H12A | 119.8 |
C4—C3—H3B | 111.2 | C12—C13—C14 | 120.11 (9) |
H3A—C3—H3B | 109.1 | C12—C13—H13A | 119.9 |
N1—C4—N2 | 102.36 (7) | C14—C13—H13A | 119.9 |
N1—C4—C11 | 110.26 (7) | C15—C14—C13 | 119.78 (9) |
N2—C4—C11 | 113.36 (7) | C15—C14—H14A | 120.1 |
N1—C4—C3 | 115.50 (7) | C13—C14—H14A | 120.1 |
N2—C4—C3 | 102.07 (7) | C14—C15—C16 | 120.27 (9) |
C11—C4—C3 | 112.65 (7) | C14—C15—H15A | 119.9 |
C6—C5—N1 | 129.53 (8) | C16—C15—H15A | 119.9 |
C6—C5—C10 | 119.99 (8) | C11—C16—C15 | 120.09 (9) |
N1—C5—C10 | 110.45 (8) | C11—C16—H16A | 120.0 |
C5—C6—C7 | 118.01 (8) | C15—C16—H16A | 120.0 |
C5—C6—H6A | 121.0 | ||
C10—N2—C1—O1 | −27.81 (15) | C7—C8—C9—C10 | −0.13 (14) |
C4—N2—C1—O1 | −171.39 (9) | C8—C9—C10—C5 | −0.07 (14) |
C10—N2—C1—C2 | 151.31 (9) | C8—C9—C10—N2 | −179.87 (9) |
C4—N2—C1—C2 | 7.74 (10) | C6—C5—C10—C9 | 0.40 (14) |
O1—C1—C2—C3 | 152.84 (9) | N1—C5—C10—C9 | −177.76 (8) |
N2—C1—C2—C3 | −26.24 (9) | C6—C5—C10—N2 | −179.76 (8) |
C1—C2—C3—C4 | 33.88 (9) | N1—C5—C10—N2 | 2.08 (10) |
C5—N1—C4—N2 | 17.45 (9) | C1—N2—C10—C9 | 44.60 (15) |
C5—N1—C4—C11 | −103.45 (8) | C4—N2—C10—C9 | −170.65 (9) |
C5—N1—C4—C3 | 127.43 (8) | C1—N2—C10—C5 | −135.22 (9) |
C1—N2—C4—N1 | 133.80 (8) | C4—N2—C10—C5 | 9.53 (9) |
C10—N2—C4—N1 | −16.51 (9) | N1—C4—C11—C16 | 111.04 (9) |
C1—N2—C4—C11 | −107.46 (8) | N2—C4—C11—C16 | −3.03 (12) |
C10—N2—C4—C11 | 102.23 (8) | C3—C4—C11—C16 | −118.31 (9) |
C1—N2—C4—C3 | 13.96 (9) | N1—C4—C11—C12 | −66.08 (10) |
C10—N2—C4—C3 | −136.34 (7) | N2—C4—C11—C12 | 179.85 (8) |
C2—C3—C4—N1 | −139.28 (8) | C3—C4—C11—C12 | 64.57 (10) |
C2—C3—C4—N2 | −29.13 (8) | C16—C11—C12—C13 | 0.20 (14) |
C2—C3—C4—C11 | 92.78 (8) | C4—C11—C12—C13 | 177.44 (8) |
C4—N1—C5—C6 | 169.27 (9) | C11—C12—C13—C14 | −0.35 (15) |
C4—N1—C5—C10 | −12.80 (10) | C12—C13—C14—C15 | 0.21 (16) |
N1—C5—C6—C7 | 177.26 (9) | C13—C14—C15—C16 | 0.08 (15) |
C10—C5—C6—C7 | −0.50 (13) | C12—C11—C16—C15 | 0.09 (14) |
C5—C6—C7—C8 | 0.30 (14) | C4—C11—C16—C15 | −176.98 (8) |
C6—C7—C8—C9 | 0.02 (14) | C14—C15—C16—C11 | −0.23 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.914 (16) | 2.112 (17) | 2.9994 (11) | 163.4 (14) |
Symmetry code: (i) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C16H14N2O |
Mr | 250.29 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 7.2966 (9), 9.1081 (11), 10.3723 (12) |
α, β, γ (°) | 66.803 (1), 88.947 (2), 82.509 (2) |
V (Å3) | 627.78 (13) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.23 × 0.20 × 0.19 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1998) |
Tmin, Tmax | 0.981, 0.984 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7155, 3492, 3259 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.694 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.125, 1.01 |
No. of reflections | 3492 |
No. of parameters | 176 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.48, −0.41 |
Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.914 (16) | 2.112 (17) | 2.9994 (11) | 163.4 (14) |
Symmetry code: (i) x−1, y, z. |
Bond | (I) | (II) | (III) | (IV) | (V) | (VI) | (VII) | (VIII) | (IX) |
N2—C10 | 1.4126 (11) | 1.416 (4) | 1.475 (2) | 1.399 (7) | 1.379 (3) | 1.397 (1) | 1.399 (2) | 1.394 (3) | 1.385 (3) |
N2—C4 | 1.4785 (11) | 1.480 (3) | 1.458 (1) | 1.491 (7) | 1.300 (3) | 1.322 (2) | 1.309 (2) | 1.315 (3) | 1.324 (3) |
N1—C5 | 1.3968 (11) | 1.374 (4) | 1.475 (2) | 1.403 (7) | 1.368 (3) | 1.381 (2) | 1.384 (2) | 1.373 (3) | 1.378 (3) |
N1—C4 | 1.4761 (11) | 1.465 (4) | 1.458 (1) | 1.480 (8) | 1.383 (3) | 1.359 (1) | 1.355 (2) | 1.352 (3) | 1.325 (3) |
C5—C10 | 1.4057 (12) | 1.388 (5) | 1.510 (3) | 1.375 (7) | 1.394 (3) | 1.394 (2) | 1.407 (2) | 1.394 (3) | 1.375 (3) |
C10—C9 | 1.3795 (12) | 1.381 (6) | 1.513 (2) | 1.383 (7) | 1.377 (3) | 1.410 (2) | 1.389 (3) | 1.387 (4) | 1.402 (3) |
C9—C8 | 1.4043 (13) | 1.388 (8) | 1.534 (2) | 1.402 (7) | 1.386 (4) | 1.397 (2) | 1.384 (3) | 1.368 (4) | 1.367 (4) |
C8—C7 | 1.3928 (13) | 1.356 (9) | 1.522 (3) | 1.389 (9) | 1.398 (3) | 1.407 (2) | 1.399 (3) | 1.391 (4) | 1.384 (3) |
C7—C6 | 1.4022 (13) | 1.380 (8) | 1.534 (2) | 1.402 (9) | 1.367 (4) | 1.382 (2) | 1.380 (2) | 1.376 (4) | 1.375 (3) |
C6—C5 | 1.3855 (12) | 1.383 (5) | 1.513 (2) | 1.363 (8) | 1.349 (4) | 1.401 (2) | 1.380 (2) | 1.386 (4) | 1.342 (3) |
Bond | (I) | (II) | (X) | (XI) | (XII) | (XIII) | (XIV) | (XV) |
N2—C1 | 1.3735 (11) | 1.354 (4) | 1.298 (4) | 1.362 (3) | 1.345 (2) | 1.3373 (13) | 1.342 (4) | 1.296 (3) |
C1—C2 | 1.5177 (13) | 1.512 (5) | 1.506 | 1.490 (4) | 1.514 (2) | 1.5294 (15) | 1.501 (5) | 1.483 (3) |
C2—C3 | 1.5375 (13) | 1.540 (4) | 1.519 | 1.437 (4) | 1.517 (2) | 1.5412 (14) | 1.472 (5) | 1.519 (3) |
C3—C4 | 1.5456 (12) | 1.539 (4) | 1.505 | 1.349 (3) | 1.524 (2) | 1.5405 (15) | 1.517 (6) | 1.516 (3) |
C4—N2 | 1.4785 (11) | 1.480 (3) | 1.449 | 1.408 (3) | 1.454 (1) | 1.4633 (14) | 1.439 (5) | 1.465 (3) |