organic compounds
5-(Prop-2-ynyl)-5H-dibenzo[b,f]azepine
aHEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
*Correspondence e-mail: dr.sammer.yousuf@gmail.com
The 17H13N, contains two independent butterfly-shaped molecules. The seven-membered azepine rings both adopt a boat conformation. The dihedral angles between the benzene rings in the two molecules are 46.95 (11) and 52.21 (11)°.
of the title compound, CRelated literature
For the biological activities of iminostilbene, see: Kumar & Naik (2010); Balaure et al. (2009); Bhatt & Patel (2005); Fuenfschilling et al. (2005); Rosowsky et al. (2004); Brzozowski & Saczewski (2002); Kulkarni et al. (1991); Arya et al. (1977). For the crystal structures of the closely related compounds, see: Jayasankar et al. (2009); Nagaraj et al. (2005); Sadashiva et al. (2005).
Experimental
Crystal data
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Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812007866/rz2705sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812007866/rz2705Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812007866/rz2705Isup3.cml
To the stirred solution of iminostilbene (0.2921 g, 1.5 mmol) in DMF (3.0 mL), propargyl bromide (0.41 ml, 4.5 mmol) and potassium carbonate (0.418 ml, 3.02 mmol) were added and refluxed for 15 h at 90°C. After completion of the reaction reaction as judged by TLC, the crude mixture was adsorbed on silica and purified by
(eluent: n-hexane:ethyl acetate, 9.5:0.5 v/v) to obtain the title compound in 77% yield. Recrystallization by slow evaporation of a methanol solution afforded yellow crystals suitable for single-crystal X-ray diffraction studies. Iminostilbene and propargyl bromide were purchased from Alfa Acer and Aldrich, respectively.Aromatic, methine and methylene H atoms were positioned geometrically with C—H = 0.93–0.97 Å, and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(CH). The hydrogen of the acetylene groups (C–H= 0.91 (2) and 0.92 (3) Å) were located in difference Fourier maps and refined isotropically.
Iminostilbene (5H-dibenzo[b,f]azepine) was found to be a valuable intermediate in medicinal chemistry. It is also a basic nucleus of many anticonvulsant drugs including carbamazepine (Balaure et al., 2009), oxazepine (Fuenfschilling et al., 2005) and imipramine (Bhatt & Patel, 2005). The structural analogue of iminostilbene showed a wide range of biological activities such as antioxidant (Kumar & Naik, 2010), antihypertensive (Arya et al., 1977), antitumor (Brzozowski & Saczewski, 2002), pesticidal (Kulkarni et al., 1991), and DHFR inhibitory activity (Rosowsky et al., 2004). The title compound was synthesized as part of our ongoing research on the synthesis of new derivatives of iminostilbene as potential anti-epileptic agents with more efficacy, low toxicity and no side effects as compared to the available drugs (Sadashiva et al., 2005).
The structure of the title compound contains two independent molecules in the
(Fig. 1). Each molecule is consists of two phenyl rings fused to a seven-membered azepine ring adopting a boat conformation. The overall shape of each molecule is butterfly-like. The dihedral angles between the phenyl rings are 46.95 (11) and 52.21 (11)° for C1–C5/C14, C6–C11 and C18–C22/C31, C23–C28, respectively. The bond lengths and angles are found to be similar to those observed in other structurally related compounds (Jayasankar et al., 2009; Nagaraj et al., 2005; Sadashiva et al., 2005). The crystal packing (Fig. 2) is enforced only by van der Waals forces.For the biological activities of iminostilbene, see: Kumar & Naik (2010); Balaure et al. (2009); Bhatt & Patel (2005); Fuenfschilling et al. (2005); Rosowsky et al. (2004); Brzozowski & Saczewski (2002); Kulkarni et al. (1991); Arya et al. (1977). For the crystal structures of the closely related compounds, see: Jayasankar et al. (2009); Nagaraj et al. (2005); Sadashiva et al. (2005).
Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. | |
Fig. 2. The crystal packing of the title compound viewed along the a axis. |
C17H13N | F(000) = 976 |
Mr = 231.28 | Dx = 1.202 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2353 reflections |
a = 11.4406 (5) Å | θ = 2.5–20.5° |
b = 10.0256 (4) Å | µ = 0.07 mm−1 |
c = 22.3155 (10) Å | T = 273 K |
β = 92.910 (1)° | Block, yellow |
V = 2556.26 (19) Å3 | 0.36 × 0.19 × 0.15 mm |
Z = 8 |
Bruker SMART APEX CCD area-detector diffractometer | 4760 independent reflections |
Radiation source: fine-focus sealed tube | 2894 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω scan | θmax = 25.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −13→13 |
Tmin = 0.975, Tmax = 0.990 | k = −12→12 |
14791 measured reflections | l = −25→27 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0567P)2 + 0.1752P] where P = (Fo2 + 2Fc2)/3 |
4760 reflections | (Δ/σ)max < 0.001 |
333 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C17H13N | V = 2556.26 (19) Å3 |
Mr = 231.28 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.4406 (5) Å | µ = 0.07 mm−1 |
b = 10.0256 (4) Å | T = 273 K |
c = 22.3155 (10) Å | 0.36 × 0.19 × 0.15 mm |
β = 92.910 (1)° |
Bruker SMART APEX CCD area-detector diffractometer | 4760 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 2894 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.990 | Rint = 0.031 |
14791 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.129 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.13 e Å−3 |
4760 reflections | Δρmin = −0.17 e Å−3 |
333 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 | 0.35570 (12) | 0.40653 (14) | 0.17436 (6) | 0.0525 (4) | |
N2 | 0.10076 (12) | 0.57540 (14) | −0.14279 (7) | 0.0564 (4) | |
C1 | 0.3841 (3) | 0.1387 (3) | 0.06172 (12) | 0.0989 (9) | |
H1A | 0.3522 | 0.0556 | 0.0520 | 0.119* | |
C2 | 0.4688 (3) | 0.1918 (4) | 0.02656 (12) | 0.1181 (13) | |
H2A | 0.4935 | 0.1447 | −0.0064 | 0.142* | |
C3 | 0.5156 (3) | 0.3127 (4) | 0.04036 (12) | 0.1084 (10) | |
H3A | 0.5714 | 0.3490 | 0.0162 | 0.130* | |
C4 | 0.4818 (2) | 0.3821 (2) | 0.08950 (10) | 0.0771 (6) | |
H4A | 0.5161 | 0.4642 | 0.0988 | 0.092* | |
C5 | 0.39677 (17) | 0.33144 (19) | 0.12571 (8) | 0.0578 (5) | |
C6 | 0.37342 (15) | 0.35079 (17) | 0.23312 (8) | 0.0514 (5) | |
C7 | 0.44563 (17) | 0.4125 (2) | 0.27675 (9) | 0.0643 (5) | |
H7A | 0.4914 | 0.4848 | 0.2664 | 0.077* | |
C8 | 0.4501 (2) | 0.3673 (2) | 0.33551 (10) | 0.0757 (6) | |
H8A | 0.4980 | 0.4099 | 0.3645 | 0.091* | |
C9 | 0.3841 (2) | 0.2598 (2) | 0.35101 (10) | 0.0780 (6) | |
H9A | 0.3852 | 0.2306 | 0.3906 | 0.094* | |
C10 | 0.31622 (19) | 0.1957 (2) | 0.30754 (10) | 0.0707 (6) | |
H10A | 0.2731 | 0.1215 | 0.3181 | 0.085* | |
C11 | 0.30968 (16) | 0.23809 (18) | 0.24806 (9) | 0.0570 (5) | |
C12 | 0.2357 (2) | 0.1663 (2) | 0.20414 (11) | 0.0782 (7) | |
H12A | 0.1695 | 0.1254 | 0.2183 | 0.094* | |
C13 | 0.2524 (2) | 0.1527 (2) | 0.14597 (12) | 0.0834 (7) | |
H13A | 0.1974 | 0.1010 | 0.1244 | 0.100* | |
C14 | 0.3450 (2) | 0.2079 (2) | 0.11208 (9) | 0.0697 (6) | |
C15 | 0.36741 (17) | 0.55153 (18) | 0.17127 (9) | 0.0644 (5) | |
H15A | 0.3342 | 0.5912 | 0.2062 | 0.077* | |
H15B | 0.4498 | 0.5748 | 0.1720 | 0.077* | |
C16 | 0.30875 (19) | 0.6063 (2) | 0.11707 (10) | 0.0678 (6) | |
C17 | 0.2623 (2) | 0.6535 (3) | 0.07470 (13) | 0.0897 (8) | |
H17A | 0.224 (2) | 0.690 (3) | 0.0417 (11) | 0.125 (10)* | |
C18 | 0.2287 (2) | 0.8931 (2) | −0.08634 (13) | 0.0902 (8) | |
H18A | 0.2908 | 0.9494 | −0.0940 | 0.108* | |
C19 | 0.1591 (3) | 0.9229 (3) | −0.04040 (14) | 0.1062 (10) | |
H19A | 0.1734 | 0.9993 | −0.0175 | 0.127* | |
C20 | 0.0687 (3) | 0.8409 (3) | −0.02805 (11) | 0.0979 (9) | |
H20A | 0.0209 | 0.8613 | 0.0032 | 0.117* | |
C21 | 0.0478 (2) | 0.7265 (2) | −0.06211 (10) | 0.0759 (6) | |
H21A | −0.0135 | 0.6701 | −0.0533 | 0.091* | |
C22 | 0.11748 (17) | 0.69593 (18) | −0.10896 (9) | 0.0576 (5) | |
C23 | 0.05986 (16) | 0.59232 (17) | −0.20371 (8) | 0.0535 (5) | |
C24 | −0.04889 (18) | 0.5457 (2) | −0.22448 (10) | 0.0688 (6) | |
H24A | −0.0993 | 0.5092 | −0.1975 | 0.083* | |
C25 | −0.0833 (2) | 0.5525 (2) | −0.28392 (11) | 0.0818 (7) | |
H25A | −0.1562 | 0.5198 | −0.2971 | 0.098* | |
C26 | −0.0107 (3) | 0.6074 (2) | −0.32395 (11) | 0.0859 (7) | |
H26A | −0.0342 | 0.6122 | −0.3644 | 0.103* | |
C27 | 0.0972 (2) | 0.65544 (19) | −0.30433 (10) | 0.0769 (6) | |
H27A | 0.1462 | 0.6926 | −0.3319 | 0.092* | |
C28 | 0.13471 (17) | 0.64939 (17) | −0.24365 (9) | 0.0591 (5) | |
C29 | 0.25089 (19) | 0.6983 (2) | −0.22446 (11) | 0.0739 (6) | |
H29A | 0.3091 | 0.6891 | −0.2518 | 0.089* | |
C30 | 0.28259 (18) | 0.7546 (2) | −0.17196 (12) | 0.0773 (7) | |
H30A | 0.3605 | 0.7805 | −0.1667 | 0.093* | |
C31 | 0.20917 (18) | 0.78001 (19) | −0.12236 (10) | 0.0645 (6) | |
C32 | 0.05539 (18) | 0.45998 (19) | −0.11137 (9) | 0.0681 (6) | |
H32A | 0.0450 | 0.3860 | −0.1391 | 0.082* | |
H32B | −0.0203 | 0.4817 | −0.0963 | 0.082* | |
C33 | 0.1359 (2) | 0.4210 (2) | −0.06140 (10) | 0.0707 (6) | |
C34 | 0.2009 (3) | 0.3889 (3) | −0.02264 (13) | 0.0962 (8) | |
H34A | 0.252 (3) | 0.361 (3) | 0.0083 (13) | 0.148 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0636 (9) | 0.0430 (8) | 0.0517 (9) | −0.0030 (7) | 0.0095 (7) | −0.0013 (7) |
N2 | 0.0611 (9) | 0.0493 (9) | 0.0591 (10) | −0.0075 (7) | 0.0062 (8) | 0.0061 (8) |
C1 | 0.149 (3) | 0.0786 (17) | 0.0660 (17) | 0.0438 (17) | −0.0289 (17) | −0.0157 (14) |
C2 | 0.164 (3) | 0.136 (3) | 0.0529 (17) | 0.089 (3) | −0.0006 (19) | −0.0074 (19) |
C3 | 0.109 (2) | 0.149 (3) | 0.0688 (18) | 0.068 (2) | 0.0261 (15) | 0.0170 (19) |
C4 | 0.0741 (14) | 0.0982 (16) | 0.0600 (14) | 0.0252 (13) | 0.0154 (12) | 0.0100 (13) |
C5 | 0.0647 (12) | 0.0612 (12) | 0.0474 (11) | 0.0154 (10) | 0.0010 (10) | 0.0009 (10) |
C6 | 0.0530 (10) | 0.0502 (10) | 0.0516 (11) | 0.0057 (9) | 0.0095 (9) | −0.0038 (9) |
C7 | 0.0680 (12) | 0.0599 (12) | 0.0651 (13) | 0.0002 (10) | 0.0047 (11) | −0.0076 (10) |
C8 | 0.0884 (16) | 0.0767 (15) | 0.0608 (14) | 0.0191 (13) | −0.0061 (12) | −0.0133 (12) |
C9 | 0.0987 (17) | 0.0787 (15) | 0.0577 (14) | 0.0303 (14) | 0.0149 (13) | 0.0067 (12) |
C10 | 0.0766 (14) | 0.0637 (13) | 0.0734 (15) | 0.0110 (11) | 0.0211 (12) | 0.0151 (11) |
C11 | 0.0597 (11) | 0.0499 (10) | 0.0621 (12) | 0.0041 (9) | 0.0102 (10) | 0.0060 (9) |
C12 | 0.0802 (15) | 0.0585 (12) | 0.0955 (18) | −0.0184 (11) | −0.0002 (14) | 0.0123 (12) |
C13 | 0.1049 (18) | 0.0552 (13) | 0.0867 (18) | −0.0142 (12) | −0.0278 (16) | −0.0035 (12) |
C14 | 0.0937 (16) | 0.0578 (12) | 0.0560 (13) | 0.0169 (12) | −0.0129 (12) | −0.0048 (11) |
C15 | 0.0732 (13) | 0.0506 (11) | 0.0703 (14) | −0.0054 (10) | 0.0119 (11) | 0.0018 (10) |
C16 | 0.0720 (13) | 0.0571 (12) | 0.0759 (15) | 0.0036 (11) | 0.0207 (12) | 0.0087 (11) |
C17 | 0.0928 (18) | 0.0917 (18) | 0.0863 (19) | 0.0256 (14) | 0.0204 (15) | 0.0225 (15) |
C18 | 0.0917 (18) | 0.0600 (14) | 0.114 (2) | −0.0077 (13) | −0.0405 (17) | 0.0088 (15) |
C19 | 0.134 (3) | 0.0695 (17) | 0.109 (2) | 0.0161 (18) | −0.051 (2) | −0.0141 (16) |
C20 | 0.124 (2) | 0.0891 (18) | 0.0779 (17) | 0.0395 (18) | −0.0167 (16) | −0.0164 (15) |
C21 | 0.0812 (15) | 0.0737 (15) | 0.0724 (15) | 0.0120 (12) | 0.0008 (13) | −0.0028 (12) |
C22 | 0.0572 (12) | 0.0541 (11) | 0.0604 (13) | 0.0046 (10) | −0.0070 (10) | 0.0053 (10) |
C23 | 0.0578 (11) | 0.0430 (10) | 0.0599 (12) | 0.0061 (9) | 0.0051 (10) | −0.0001 (9) |
C24 | 0.0649 (13) | 0.0697 (13) | 0.0716 (14) | −0.0026 (10) | 0.0015 (11) | −0.0085 (11) |
C25 | 0.0873 (16) | 0.0726 (15) | 0.0835 (17) | 0.0015 (13) | −0.0152 (14) | −0.0139 (13) |
C26 | 0.124 (2) | 0.0647 (14) | 0.0671 (15) | 0.0149 (15) | −0.0145 (16) | −0.0056 (12) |
C27 | 0.1099 (19) | 0.0537 (12) | 0.0688 (15) | 0.0136 (13) | 0.0202 (14) | 0.0115 (11) |
C28 | 0.0664 (13) | 0.0448 (10) | 0.0671 (13) | 0.0103 (9) | 0.0126 (11) | 0.0090 (9) |
C29 | 0.0647 (14) | 0.0627 (13) | 0.0965 (18) | 0.0107 (11) | 0.0263 (13) | 0.0264 (13) |
C30 | 0.0504 (12) | 0.0679 (14) | 0.113 (2) | −0.0065 (11) | −0.0060 (14) | 0.0334 (14) |
C31 | 0.0581 (12) | 0.0525 (12) | 0.0811 (15) | −0.0037 (10) | −0.0157 (12) | 0.0121 (11) |
C32 | 0.0734 (13) | 0.0601 (12) | 0.0718 (14) | −0.0131 (11) | 0.0123 (11) | 0.0080 (11) |
C33 | 0.0866 (15) | 0.0601 (13) | 0.0671 (14) | 0.0002 (11) | 0.0198 (13) | 0.0117 (11) |
C34 | 0.111 (2) | 0.0952 (19) | 0.0827 (19) | 0.0185 (16) | 0.0100 (17) | 0.0232 (15) |
N1—C5 | 1.420 (2) | C15—H15B | 0.9700 |
N1—C6 | 1.431 (2) | C16—C17 | 1.162 (3) |
N1—C15 | 1.462 (2) | C17—H17A | 0.91 (2) |
N2—C23 | 1.425 (2) | C18—C19 | 1.362 (4) |
N2—C22 | 1.432 (2) | C18—C31 | 1.401 (3) |
N2—C32 | 1.462 (2) | C18—H18A | 0.9300 |
C1—C2 | 1.385 (4) | C19—C20 | 1.361 (4) |
C1—C14 | 1.413 (3) | C19—H19A | 0.9300 |
C1—H1A | 0.9300 | C20—C21 | 1.390 (3) |
C2—C3 | 1.354 (4) | C20—H20A | 0.9300 |
C2—H2A | 0.9300 | C21—C22 | 1.381 (3) |
C3—C4 | 1.371 (3) | C21—H21A | 0.9300 |
C3—H3A | 0.9300 | C22—C31 | 1.390 (3) |
C4—C5 | 1.392 (3) | C23—C24 | 1.387 (3) |
C4—H4A | 0.9300 | C23—C28 | 1.390 (3) |
C5—C14 | 1.399 (3) | C24—C25 | 1.366 (3) |
C6—C7 | 1.390 (2) | C24—H24A | 0.9300 |
C6—C11 | 1.394 (2) | C25—C26 | 1.366 (3) |
C7—C8 | 1.386 (3) | C25—H25A | 0.9300 |
C7—H7A | 0.9300 | C26—C27 | 1.376 (3) |
C8—C9 | 1.371 (3) | C26—H26A | 0.9300 |
C8—H8A | 0.9300 | C27—C28 | 1.401 (3) |
C9—C10 | 1.371 (3) | C27—H27A | 0.9300 |
C9—H9A | 0.9300 | C28—C29 | 1.460 (3) |
C10—C11 | 1.392 (3) | C29—C30 | 1.334 (3) |
C10—H10A | 0.9300 | C29—H29A | 0.9300 |
C11—C12 | 1.453 (3) | C30—C31 | 1.446 (3) |
C12—C13 | 1.329 (3) | C30—H30A | 0.9300 |
C12—H12A | 0.9300 | C32—C33 | 1.463 (3) |
C13—C14 | 1.444 (3) | C32—H32A | 0.9700 |
C13—H13A | 0.9300 | C32—H32B | 0.9700 |
C15—C16 | 1.460 (3) | C33—C34 | 1.157 (3) |
C15—H15A | 0.9700 | C34—H34A | 0.92 (3) |
C5—N1—C6 | 117.16 (14) | H15A—C15—H15B | 107.9 |
C5—N1—C15 | 117.16 (15) | C17—C16—C15 | 178.0 (2) |
C6—N1—C15 | 114.99 (14) | C16—C17—H17A | 178.5 (18) |
C23—N2—C22 | 115.52 (13) | C19—C18—C31 | 121.8 (3) |
C23—N2—C32 | 116.38 (14) | C19—C18—H18A | 119.1 |
C22—N2—C32 | 117.14 (15) | C31—C18—H18A | 119.1 |
C2—C1—C14 | 121.4 (3) | C20—C19—C18 | 119.9 (3) |
C2—C1—H1A | 119.3 | C20—C19—H19A | 120.0 |
C14—C1—H1A | 119.3 | C18—C19—H19A | 120.0 |
C3—C2—C1 | 119.7 (3) | C19—C20—C21 | 120.0 (3) |
C3—C2—H2A | 120.1 | C19—C20—H20A | 120.0 |
C1—C2—H2A | 120.1 | C21—C20—H20A | 120.0 |
C2—C3—C4 | 120.8 (3) | C22—C21—C20 | 120.5 (2) |
C2—C3—H3A | 119.6 | C22—C21—H21A | 119.8 |
C4—C3—H3A | 119.6 | C20—C21—H21A | 119.8 |
C3—C4—C5 | 120.9 (3) | C21—C22—C31 | 119.9 (2) |
C3—C4—H4A | 119.6 | C21—C22—N2 | 121.30 (18) |
C5—C4—H4A | 119.6 | C31—C22—N2 | 118.7 (2) |
C4—C5—C14 | 119.8 (2) | C24—C23—C28 | 119.72 (18) |
C4—C5—N1 | 121.21 (18) | C24—C23—N2 | 121.62 (18) |
C14—C5—N1 | 118.85 (19) | C28—C23—N2 | 118.52 (16) |
C7—C6—C11 | 119.52 (17) | C25—C24—C23 | 121.2 (2) |
C7—C6—N1 | 121.33 (16) | C25—C24—H24A | 119.4 |
C11—C6—N1 | 118.96 (15) | C23—C24—H24A | 119.4 |
C8—C7—C6 | 120.6 (2) | C24—C25—C26 | 120.0 (2) |
C8—C7—H7A | 119.7 | C24—C25—H25A | 120.0 |
C6—C7—H7A | 119.7 | C26—C25—H25A | 120.0 |
C9—C8—C7 | 120.1 (2) | C25—C26—C27 | 119.9 (2) |
C9—C8—H8A | 120.0 | C25—C26—H26A | 120.0 |
C7—C8—H8A | 120.0 | C27—C26—H26A | 120.0 |
C10—C9—C8 | 119.3 (2) | C26—C27—C28 | 121.2 (2) |
C10—C9—H9A | 120.4 | C26—C27—H27A | 119.4 |
C8—C9—H9A | 120.4 | C28—C27—H27A | 119.4 |
C9—C10—C11 | 122.2 (2) | C23—C28—C27 | 117.99 (19) |
C9—C10—H10A | 118.9 | C23—C28—C29 | 122.09 (18) |
C11—C10—H10A | 118.9 | C27—C28—C29 | 119.9 (2) |
C10—C11—C6 | 118.14 (18) | C30—C29—C28 | 127.0 (2) |
C10—C11—C12 | 119.56 (19) | C30—C29—H29A | 116.5 |
C6—C11—C12 | 122.28 (18) | C28—C29—H29A | 116.5 |
C13—C12—C11 | 127.0 (2) | C29—C30—C31 | 127.2 (2) |
C13—C12—H12A | 116.5 | C29—C30—H30A | 116.4 |
C11—C12—H12A | 116.5 | C31—C30—H30A | 116.4 |
C12—C13—C14 | 128.2 (2) | C22—C31—C18 | 117.9 (2) |
C12—C13—H13A | 115.9 | C22—C31—C30 | 122.15 (19) |
C14—C13—H13A | 115.9 | C18—C31—C30 | 120.0 (2) |
C5—C14—C1 | 117.4 (2) | N2—C32—C33 | 110.60 (16) |
C5—C14—C13 | 122.65 (19) | N2—C32—H32A | 109.5 |
C1—C14—C13 | 119.9 (2) | C33—C32—H32A | 109.5 |
C16—C15—N1 | 111.94 (16) | N2—C32—H32B | 109.5 |
C16—C15—H15A | 109.2 | C33—C32—H32B | 109.5 |
N1—C15—H15A | 109.2 | H32A—C32—H32B | 108.1 |
C16—C15—H15B | 109.2 | C34—C33—C32 | 178.7 (3) |
N1—C15—H15B | 109.2 | C33—C34—H34A | 178 (2) |
C14—C1—C2—C3 | −0.1 (4) | C31—C18—C19—C20 | 0.8 (4) |
C1—C2—C3—C4 | 1.3 (4) | C18—C19—C20—C21 | 0.3 (4) |
C2—C3—C4—C5 | −1.3 (4) | C19—C20—C21—C22 | −0.7 (3) |
C3—C4—C5—C14 | 0.1 (3) | C20—C21—C22—C31 | −0.1 (3) |
C3—C4—C5—N1 | −175.84 (18) | C20—C21—C22—N2 | 177.06 (17) |
C6—N1—C5—C4 | −118.89 (18) | C23—N2—C22—C21 | 112.72 (19) |
C15—N1—C5—C4 | 24.0 (2) | C32—N2—C22—C21 | −30.2 (2) |
C6—N1—C5—C14 | 65.1 (2) | C23—N2—C22—C31 | −70.1 (2) |
C15—N1—C5—C14 | −152.05 (16) | C32—N2—C22—C31 | 146.96 (17) |
C5—N1—C6—C7 | 115.39 (19) | C22—N2—C23—C24 | −115.27 (19) |
C15—N1—C6—C7 | −28.3 (2) | C32—N2—C23—C24 | 28.0 (2) |
C5—N1—C6—C11 | −69.7 (2) | C22—N2—C23—C28 | 68.9 (2) |
C15—N1—C6—C11 | 146.70 (17) | C32—N2—C23—C28 | −147.85 (17) |
C11—C6—C7—C8 | −3.4 (3) | C28—C23—C24—C25 | 1.2 (3) |
N1—C6—C7—C8 | 171.53 (17) | N2—C23—C24—C25 | −174.52 (17) |
C6—C7—C8—C9 | 0.8 (3) | C23—C24—C25—C26 | −0.8 (3) |
C7—C8—C9—C10 | 1.7 (3) | C24—C25—C26—C27 | 0.1 (3) |
C8—C9—C10—C11 | −1.6 (3) | C25—C26—C27—C28 | 0.0 (3) |
C9—C10—C11—C6 | −1.0 (3) | C24—C23—C28—C27 | −1.1 (3) |
C9—C10—C11—C12 | −179.7 (2) | N2—C23—C28—C27 | 174.82 (16) |
C7—C6—C11—C10 | 3.4 (3) | C24—C23—C28—C29 | −179.05 (18) |
N1—C6—C11—C10 | −171.60 (16) | N2—C23—C28—C29 | −3.2 (3) |
C7—C6—C11—C12 | −177.87 (18) | C26—C27—C28—C23 | 0.5 (3) |
N1—C6—C11—C12 | 7.1 (3) | C26—C27—C28—C29 | 178.50 (19) |
C10—C11—C12—C13 | −149.7 (2) | C23—C28—C29—C30 | −34.1 (3) |
C6—C11—C12—C13 | 31.6 (3) | C27—C28—C29—C30 | 147.9 (2) |
C11—C12—C13—C14 | −1.8 (4) | C28—C29—C30—C31 | 0.0 (3) |
C4—C5—C14—C1 | 1.0 (3) | C21—C22—C31—C18 | 1.2 (3) |
N1—C5—C14—C1 | 177.08 (16) | N2—C22—C31—C18 | −176.05 (16) |
C4—C5—C14—C13 | −176.86 (19) | C21—C22—C31—C30 | −178.21 (17) |
N1—C5—C14—C13 | −0.8 (3) | N2—C22—C31—C30 | 4.6 (3) |
C2—C1—C14—C5 | −1.1 (3) | C19—C18—C31—C22 | −1.6 (3) |
C2—C1—C14—C13 | 176.9 (2) | C19—C18—C31—C30 | 177.8 (2) |
C12—C13—C14—C5 | −32.8 (3) | C29—C30—C31—C22 | 33.3 (3) |
C12—C13—C14—C1 | 149.4 (2) | C29—C30—C31—C18 | −146.1 (2) |
C5—N1—C15—C16 | 57.1 (2) | C23—N2—C32—C33 | 155.99 (17) |
C6—N1—C15—C16 | −159.25 (16) | C22—N2—C32—C33 | −61.4 (2) |
Experimental details
Crystal data | |
Chemical formula | C17H13N |
Mr | 231.28 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 273 |
a, b, c (Å) | 11.4406 (5), 10.0256 (4), 22.3155 (10) |
β (°) | 92.910 (1) |
V (Å3) | 2556.26 (19) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.36 × 0.19 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.975, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14791, 4760, 2894 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.129, 1.02 |
No. of reflections | 4760 |
No. of parameters | 333 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.13, −0.17 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Iminostilbene (5H-dibenzo[b,f]azepine) was found to be a valuable intermediate in medicinal chemistry. It is also a basic nucleus of many anticonvulsant drugs including carbamazepine (Balaure et al., 2009), oxazepine (Fuenfschilling et al., 2005) and imipramine (Bhatt & Patel, 2005). The structural analogue of iminostilbene showed a wide range of biological activities such as antioxidant (Kumar & Naik, 2010), antihypertensive (Arya et al., 1977), antitumor (Brzozowski & Saczewski, 2002), pesticidal (Kulkarni et al., 1991), and DHFR inhibitory activity (Rosowsky et al., 2004). The title compound was synthesized as part of our ongoing research on the synthesis of new derivatives of iminostilbene as potential anti-epileptic agents with more efficacy, low toxicity and no side effects as compared to the available drugs (Sadashiva et al., 2005).
The structure of the title compound contains two independent molecules in the asymmetric unit (Fig. 1). Each molecule is consists of two phenyl rings fused to a seven-membered azepine ring adopting a boat conformation. The overall shape of each molecule is butterfly-like. The dihedral angles between the phenyl rings are 46.95 (11) and 52.21 (11)° for C1–C5/C14, C6–C11 and C18–C22/C31, C23–C28, respectively. The bond lengths and angles are found to be similar to those observed in other structurally related compounds (Jayasankar et al., 2009; Nagaraj et al., 2005; Sadashiva et al., 2005). The crystal packing (Fig. 2) is enforced only by van der Waals forces.