5-(Prop-2-yn-1-yl)-5H-dibenzo[b,f]azepine: ortho-rhom-bic polymorph.

In the title ortho-rhom-bic polymorph (space group Iba2), C17H13N, the dihedral angle between the benzene rings is 55.99 (10)° and the azepine ring adopts a boat conformation. In the crystal, mol-ecules are linked by C-H⋯π contacts. The previously-reported polymorph [Yousuf et al. (2012 ▶). Acta Cryst. E68, o1101] crystallizes in the monoclinic system (space group P21/c) with two mol-ecules in the asymmetric unit.

Related literature

For the previously-reported monoclinic polymorph, see: Yousuf et al. (2012 ▶). For biochemical background, see: Sadashiva et al. (2005 ▶).

Experimental

Crystal data

C17H13N

M = 231.28

Orthorhombic,

a = 16.2444 (6) Å

b = 21.1700 (6) Å

c = 7.2399 (2) Å

V = 2489.76 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 103 K

0.35 × 0.30 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

10081 measured reflections

1199 independent reflections

1132 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.067

S = 1.09

1199 reflections

164 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.08 e Å−3

Δρmin = −0.10 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812048908/hb6998sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048908/hb6998Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812048908/hb6998Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H13N	F(000) = 976
Mr = 231.28	Dx = 1.234 Mg m−3
Orthorhombic, Iba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: I 2 -2c	Cell parameters from 1199 reflections
a = 16.2444 (6) Å	θ = 3.2–25.0°
b = 21.1700 (6) Å	µ = 0.07 mm−1
c = 7.2399 (2) Å	T = 103 K
V = 2489.76 (13) Å3	Block, yellow
Z = 8	0.35 × 0.30 × 0.25 mm

Oxford Diffraction Xcalibur Eos diffractometer	1132 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 25.0°, θmin = 3.2°
Detector resolution: 16.0839 pixels mm-1	h = −19→19
ω scans	k = −25→25
10081 measured reflections	l = −8→8
1199 independent reflections

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)] = 0.026	H-atom parameters constrained
wR(F2) = 0.067	w = 1/[σ2(Fo2) + (0.0354P)2 + 0.3725P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
1199 reflections	Δρmax = 0.08 e Å−3
164 parameters	Δρmin = −0.10 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0046 (6)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.23053 (8)	0.36797 (6)	0.6618 (2)	0.0409 (4)
C2	0.31311 (10)	0.36894 (7)	0.5957 (3)	0.0414 (5)
C3	0.34432 (10)	0.42627 (8)	0.5292 (3)	0.0492 (6)
C4	0.29519 (12)	0.48379 (8)	0.5170 (3)	0.0560 (6)
C5	0.21579 (11)	0.48775 (7)	0.4806 (3)	0.0538 (6)
C6	0.15967 (10)	0.43569 (8)	0.4423 (3)	0.0450 (5)
C7	0.16937 (9)	0.37583 (7)	0.5219 (2)	0.0399 (5)
C8	0.11790 (10)	0.32691 (8)	0.4686 (3)	0.0483 (6)
C9	0.05556 (11)	0.33719 (9)	0.3419 (3)	0.0592 (7)
C10	0.04355 (11)	0.39633 (10)	0.2688 (3)	0.0635 (7)
C11	0.09515 (11)	0.44467 (9)	0.3192 (3)	0.0571 (6)
C12	0.36307 (11)	0.31589 (9)	0.5992 (3)	0.0532 (6)
C13	0.44347 (12)	0.31917 (11)	0.5374 (3)	0.0705 (8)
C14	0.47460 (12)	0.37508 (13)	0.4711 (4)	0.0791 (9)
C15	0.42559 (12)	0.42769 (11)	0.4679 (4)	0.0691 (8)
C16	0.21109 (11)	0.32276 (8)	0.8082 (3)	0.0491 (6)
C17	0.26199 (11)	0.33371 (8)	0.9703 (3)	0.0474 (6)
C18	0.30303 (14)	0.34250 (9)	1.1020 (3)	0.0616 (7)
H4	0.32340	0.52250	0.53740	0.0670*
H5	0.19270	0.52900	0.47920	0.0650*
H8	0.12550	0.28600	0.51950	0.0580*
H9	0.02100	0.30320	0.30540	0.0710*
H10	−0.00010	0.40370	0.18410	0.0760*
H11	0.08650	0.48550	0.26830	0.0690*
H12	0.34190	0.27700	0.64430	0.0640*
H13	0.47730	0.28260	0.54070	0.0850*
H14	0.52970	0.37720	0.42790	0.0950*
H15	0.44760	0.46630	0.42260	0.0830*
H16A	0.15230	0.32680	0.84240	0.0590*
H16B	0.22030	0.27930	0.76240	0.0590*
H18	0.33610	0.34960	1.20820	0.0740*

	U11	U22	U33	U12	U13	U23
N1	0.0432 (7)	0.0429 (7)	0.0367 (8)	−0.0037 (6)	0.0005 (6)	0.0061 (6)
C2	0.0424 (8)	0.0505 (9)	0.0314 (8)	−0.0034 (8)	−0.0036 (8)	−0.0045 (7)
C3	0.0494 (9)	0.0594 (10)	0.0389 (10)	−0.0153 (8)	−0.0019 (8)	−0.0043 (8)
C4	0.0762 (12)	0.0439 (10)	0.0479 (11)	−0.0187 (8)	0.0020 (10)	−0.0015 (8)
C5	0.0747 (11)	0.0393 (9)	0.0474 (11)	0.0003 (8)	0.0066 (11)	0.0039 (8)
C6	0.0506 (9)	0.0464 (8)	0.0380 (9)	0.0061 (7)	0.0079 (8)	0.0023 (8)
C7	0.0385 (8)	0.0449 (8)	0.0362 (9)	0.0031 (7)	0.0050 (7)	−0.0001 (7)
C8	0.0464 (9)	0.0486 (9)	0.0498 (11)	−0.0009 (8)	−0.0006 (9)	−0.0001 (8)
C9	0.0498 (10)	0.0693 (12)	0.0584 (13)	−0.0044 (9)	−0.0072 (10)	−0.0051 (10)
C10	0.0506 (10)	0.0866 (14)	0.0533 (13)	0.0091 (11)	−0.0072 (10)	0.0044 (12)
C11	0.0574 (11)	0.0628 (11)	0.0511 (11)	0.0143 (9)	0.0018 (10)	0.0122 (9)
C12	0.0539 (10)	0.0610 (11)	0.0448 (11)	0.0056 (9)	−0.0074 (9)	−0.0068 (9)
C13	0.0560 (11)	0.1000 (17)	0.0554 (13)	0.0212 (12)	−0.0066 (11)	−0.0157 (13)
C14	0.0453 (11)	0.131 (2)	0.0610 (14)	−0.0082 (12)	0.0035 (11)	−0.0112 (15)
C15	0.0540 (11)	0.0919 (15)	0.0615 (13)	−0.0257 (11)	0.0031 (11)	−0.0036 (13)
C16	0.0545 (10)	0.0483 (9)	0.0446 (11)	−0.0065 (8)	−0.0006 (9)	0.0095 (8)
C17	0.0632 (11)	0.0407 (8)	0.0384 (10)	−0.0004 (8)	0.0064 (10)	0.0056 (8)
C18	0.0885 (15)	0.0558 (11)	0.0404 (11)	−0.0061 (11)	−0.0077 (11)	0.0014 (9)

N1—C2	1.424 (2)	C14—C15	1.369 (3)
N1—C7	1.429 (2)	C16—C17	1.454 (3)
N1—C16	1.463 (2)	C17—C18	1.178 (3)
C2—C3	1.401 (2)	C4—H4	0.9500
C2—C12	1.386 (2)	C5—H5	0.9500
C3—C4	1.459 (2)	C8—H8	0.9500
C3—C15	1.393 (3)	C9—H9	0.9500
C4—C5	1.319 (3)	C10—H10	0.9500
C5—C6	1.457 (2)	C11—H11	0.9500
C6—C7	1.401 (2)	C12—H12	0.9500
C6—C11	1.389 (3)	C13—H13	0.9500
C7—C8	1.386 (2)	C14—H14	0.9500
C8—C9	1.384 (3)	C15—H15	0.9500
C9—C10	1.373 (3)	C16—H16A	0.9900
C10—C11	1.372 (3)	C16—H16B	0.9900
C12—C13	1.382 (3)	C18—H18	0.9500
C13—C14	1.374 (4)
C2—N1—C7	114.53 (14)	C3—C4—H4	117.00
C2—N1—C16	117.15 (13)	C5—C4—H4	117.00
C7—N1—C16	116.10 (13)	C4—C5—H5	117.00
N1—C2—C3	117.96 (14)	C6—C5—H5	116.00
N1—C2—C12	122.26 (15)	C7—C8—H8	120.00
C3—C2—C12	119.77 (16)	C9—C8—H8	120.00
C2—C3—C4	123.10 (16)	C8—C9—H9	120.00
C2—C3—C15	118.11 (17)	C10—C9—H9	120.00
C4—C3—C15	118.76 (17)	C9—C10—H10	120.00
C3—C4—C5	126.88 (16)	C11—C10—H10	120.00
C4—C5—C6	127.00 (15)	C6—C11—H11	119.00
C5—C6—C7	122.38 (16)	C10—C11—H11	119.00
C5—C6—C11	119.39 (16)	C2—C12—H12	120.00
C7—C6—C11	118.21 (15)	C13—C12—H12	120.00
N1—C7—C6	118.38 (14)	C12—C13—H13	120.00
N1—C7—C8	122.01 (14)	C14—C13—H13	120.00
C6—C7—C8	119.58 (15)	C13—C14—H14	120.00
C7—C8—C9	120.57 (16)	C15—C14—H14	120.00
C8—C9—C10	120.19 (17)	C3—C15—H15	119.00
C9—C10—C11	119.39 (18)	C14—C15—H15	119.00
C6—C11—C10	121.97 (18)	N1—C16—H16A	109.00
C2—C12—C13	120.44 (18)	N1—C16—H16B	109.00
C12—C13—C14	120.3 (2)	C17—C16—H16A	109.00
C13—C14—C15	119.5 (2)	C17—C16—H16B	109.00
C3—C15—C14	121.9 (2)	H16A—C16—H16B	108.00
N1—C16—C17	110.96 (14)	C17—C18—H18	180.00
C16—C17—C18	179.8 (2)
C7—N1—C2—C3	69.0 (2)	C4—C3—C15—C14	−178.4 (2)
C7—N1—C2—C12	−112.4 (2)	C3—C4—C5—C6	−0.8 (4)
C16—N1—C2—C3	−149.95 (18)	C4—C5—C6—C7	32.0 (3)
C16—N1—C2—C12	28.6 (3)	C4—C5—C6—C11	−146.4 (2)
C2—N1—C7—C6	−72.36 (18)	C5—C6—C7—N1	7.6 (3)
C2—N1—C7—C8	110.12 (17)	C5—C6—C7—C8	−174.84 (18)
C16—N1—C7—C6	146.21 (16)	C11—C6—C7—N1	−174.02 (16)
C16—N1—C7—C8	−31.3 (2)	C11—C6—C7—C8	3.6 (3)
C2—N1—C16—C17	58.9 (2)	C5—C6—C11—C10	175.77 (19)
C7—N1—C16—C17	−160.75 (14)	C7—C6—C11—C10	−2.7 (3)
N1—C2—C3—C4	−2.9 (3)	N1—C7—C8—C9	175.51 (16)
N1—C2—C3—C15	178.7 (2)	C6—C7—C8—C9	−2.0 (3)
C12—C2—C3—C4	178.5 (2)	C7—C8—C9—C10	−0.6 (3)
C12—C2—C3—C15	0.1 (3)	C8—C9—C10—C11	1.6 (3)
N1—C2—C12—C13	−178.59 (19)	C9—C10—C11—C6	0.1 (3)
C3—C2—C12—C13	0.0 (3)	C2—C12—C13—C14	−0.3 (3)
C2—C3—C4—C5	−33.6 (4)	C12—C13—C14—C15	0.5 (4)
C15—C3—C4—C5	144.8 (2)	C13—C14—C15—C3	−0.4 (4)
C2—C3—C15—C14	0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cg2i	0.95	2.75	3.659 (2)	160
C18—H18···Cg1ii	0.95	2.58	3.512 (2)	167

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2/C3/C12–C15 and C6-C11 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯Cg2i	0.95	2.75	3.659 (2)	160
C18—H18⋯Cg1ii	0.95	2.58	3.512 (2)	167

Symmetry codes: (i) ; (ii) .