9-Chloro-1-methyl-7-phenyl-5,6-dihydro-13H-indolo[3,2-c]acridine.

The title compound, C(26)H(19)ClN(2), is a 5,6-dihydro-13H-indolo[3,2-c]acridine prepared by condensation of a 2,3,4,9-tetra-hydro-1H-carbazol-1-one with 2-amino-benzophenone. The crystals undergo a destructive phase change upon cooling at varying temperatures between 270 and 200 K, depending on cooling rate and disturbance by vibration, thus indicating supercooling of the metastable room-temperature structure at lower temperature. The overall planarity of the indolo[3,2-c]acridine part of the mol-ecule is inter-rupted by the saturated ethyl-ene group, and the planes of the two halves exhibit a dihedral angle of 22.05 (6)° with each other while themselves being essentially planar. Packing is dominated by C-H⋯π inter-actions. No classical hydrogen bonds or stacking inter-actions are observed.

Related literature

For general background on the synthesis and properties of carbazole derivatives, see: Knölker & Reddy (2002 ▶); Choi et al. (2008 ▶). For synthesis and structures of indoloacridines, see: Sridharan et al. (2009a ▶,b ▶). For pharmacologically active constituents (especially carbazole alkaloids) of Murraya koenigii spreng, see: Iyer & Devi (2008 ▶).

Experimental

Crystal data

C26H19ClN2

M = 394.88

Triclinic,

a = 9.981 (4) Å

b = 10.057 (4) Å

c = 10.281 (4) Å

α = 76.459 (7)°

β = 80.279 (7)°

γ = 81.754 (7)°

V = 983.1 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.21 mm−1

T = 293 K

0.55 × 0.20 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.851, T max = 0.975

10234 measured reflections

4857 independent reflections

2826 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.124

S = 1.02

4857 reflections

263 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.24 e Å−3

Data collection and cell refinement: APEX2 (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and Mercury (Macrae et al., 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013737/fl2247sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013737/fl2247Isup2.hkl

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

C26H19ClN2	Z = 2
Mr = 394.88	F(000) = 412
Triclinic, P1	Dx = 1.334 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.981 (4) Å	Cell parameters from 417 reflections
b = 10.057 (4) Å	θ = 2.6–30.3°
c = 10.281 (4) Å	µ = 0.21 mm−1
α = 76.459 (7)°	T = 293 K
β = 80.279 (7)°	Needle, yellow
γ = 81.754 (7)°	0.55 × 0.20 × 0.12 mm
V = 983.1 (7) Å3

Bruker SMART APEX CCD diffractometer	4857 independent reflections
Radiation source: fine-focus sealed tube	2826 reflections with I > 2σ(I)
graphite	Rint = 0.038
ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (APEX2; Bruker, 2008)	h = −13→13
Tmin = 0.851, Tmax = 0.975	k = −13→13
10234 measured reflections	l = −13→13

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0406P)2 + 0.0904P] where P = (Fo2 + 2Fc2)/3
4857 reflections	(Δ/σ)max = 0.001
263 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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
C1	1.0539 (2)	0.6878 (2)	0.9185 (2)	0.0377 (5)
C2	1.1590 (2)	0.6123 (2)	0.8474 (2)	0.0483 (6)
H2	1.1628	0.6231	0.7546	0.058*
C3	1.2550 (2)	0.5237 (2)	0.9125 (2)	0.0499 (6)
H3	1.3237	0.4741	0.8645	0.060*
C4	1.2495 (2)	0.5079 (2)	1.0516 (2)	0.0433 (5)
C5	1.1507 (2)	0.5793 (2)	1.1249 (2)	0.0401 (5)
H5	1.1498	0.5674	1.2175	0.048*
C6	1.04930 (19)	0.6717 (2)	1.05958 (19)	0.0360 (5)
C7	0.9424 (2)	0.7498 (2)	1.12968 (19)	0.0366 (5)
C8	0.8504 (2)	0.8392 (2)	1.0570 (2)	0.0384 (5)
C9	0.7306 (2)	0.9240 (2)	1.1197 (2)	0.0481 (6)
H9A	0.7504	0.9349	1.2056	0.058*
H9B	0.6509	0.8741	1.1379	0.058*
C10	0.6961 (2)	1.0667 (2)	1.0325 (2)	0.0481 (6)
H10A	0.6064	1.1058	1.0675	0.058*
H10B	0.7625	1.1270	1.0357	0.058*
C11	0.6973 (2)	1.0559 (2)	0.8900 (2)	0.0399 (5)
C12	0.6403 (2)	1.1467 (2)	0.7787 (2)	0.0406 (5)
C13	0.5656 (2)	1.2770 (2)	0.7608 (2)	0.0509 (6)
H13	0.5405	1.3216	0.8323	0.061*
C14	0.5304 (2)	1.3371 (3)	0.6356 (3)	0.0607 (7)
H14	0.4825	1.4245	0.6219	0.073*
C15	0.5649 (2)	1.2703 (3)	0.5283 (3)	0.0606 (7)
H15	0.5364	1.3135	0.4457	0.073*
C16	0.6396 (2)	1.1428 (2)	0.5396 (2)	0.0496 (6)
C17	0.6786 (2)	1.0840 (2)	0.6669 (2)	0.0412 (5)
C18	0.7711 (2)	0.9486 (2)	0.8411 (2)	0.0388 (5)
C19	0.8654 (2)	0.8472 (2)	0.91467 (19)	0.0370 (5)
C20	0.6795 (3)	1.0715 (3)	0.4238 (2)	0.0692 (8)
H20A	0.6358	1.1226	0.3482	0.104*
H20B	0.6512	0.9805	0.4503	0.104*
H20C	0.7769	1.0657	0.3987	0.104*
C21	0.9294 (2)	0.7292 (2)	1.27990 (19)	0.0373 (5)
C22	0.8344 (2)	0.6490 (3)	1.3624 (2)	0.0557 (6)
H22	0.7773	0.6089	1.3236	0.067*
C23	0.8222 (3)	0.6269 (3)	1.5009 (2)	0.0594 (7)
H23	0.7574	0.5723	1.5548	0.071*
C24	0.9056 (2)	0.6854 (2)	1.5591 (2)	0.0493 (6)
H24	0.8983	0.6703	1.6527	0.059*
C25	0.9988 (3)	0.7656 (3)	1.4794 (2)	0.0608 (7)
H25	1.0548	0.8065	1.5188	0.073*
C26	1.0116 (2)	0.7874 (3)	1.3397 (2)	0.0575 (7)
H26	1.0767	0.8420	1.2864	0.069*
Cl2	1.37259 (6)	0.39220 (7)	1.13247 (6)	0.0601 (2)
N1	0.96084 (17)	0.77544 (17)	0.84684 (16)	0.0407 (4)
N2	0.75957 (17)	0.96338 (17)	0.70665 (17)	0.0433 (4)
H2A	0.7966	0.9069	0.6563	0.052*

	U11	U22	U33	U12	U13	U23
C1	0.0383 (11)	0.0386 (12)	0.0376 (11)	−0.0026 (9)	−0.0047 (9)	−0.0122 (9)
C2	0.0522 (13)	0.0554 (15)	0.0375 (12)	0.0053 (11)	−0.0065 (10)	−0.0170 (11)
C3	0.0457 (13)	0.0552 (15)	0.0493 (13)	0.0090 (11)	−0.0070 (10)	−0.0208 (12)
C4	0.0414 (12)	0.0400 (12)	0.0476 (13)	0.0002 (10)	−0.0110 (10)	−0.0069 (10)
C5	0.0420 (12)	0.0422 (13)	0.0352 (11)	−0.0035 (10)	−0.0069 (9)	−0.0059 (10)
C6	0.0382 (11)	0.0361 (11)	0.0348 (11)	−0.0046 (9)	−0.0044 (9)	−0.0098 (9)
C7	0.0406 (11)	0.0359 (12)	0.0335 (10)	−0.0060 (9)	−0.0032 (9)	−0.0084 (9)
C8	0.0400 (11)	0.0383 (12)	0.0363 (11)	−0.0038 (9)	−0.0015 (9)	−0.0098 (9)
C9	0.0495 (13)	0.0506 (14)	0.0398 (12)	0.0051 (11)	−0.0006 (10)	−0.0109 (11)
C10	0.0538 (14)	0.0446 (14)	0.0448 (13)	0.0035 (11)	−0.0038 (10)	−0.0147 (11)
C11	0.0397 (11)	0.0359 (12)	0.0427 (12)	−0.0005 (9)	−0.0038 (9)	−0.0094 (10)
C12	0.0360 (11)	0.0391 (12)	0.0455 (12)	−0.0003 (10)	−0.0040 (9)	−0.0105 (10)
C13	0.0504 (14)	0.0418 (13)	0.0583 (15)	0.0047 (11)	−0.0051 (11)	−0.0139 (12)
C14	0.0621 (16)	0.0425 (14)	0.0703 (17)	0.0089 (12)	−0.0152 (13)	−0.0026 (13)
C15	0.0665 (16)	0.0538 (16)	0.0576 (15)	0.0043 (13)	−0.0236 (13)	−0.0002 (13)
C16	0.0544 (14)	0.0459 (14)	0.0491 (14)	−0.0024 (11)	−0.0170 (11)	−0.0064 (11)
C17	0.0403 (12)	0.0358 (12)	0.0474 (13)	−0.0007 (10)	−0.0109 (9)	−0.0076 (10)
C18	0.0438 (12)	0.0377 (12)	0.0352 (11)	−0.0016 (10)	−0.0073 (9)	−0.0090 (9)
C19	0.0402 (11)	0.0356 (12)	0.0361 (11)	−0.0023 (9)	−0.0048 (9)	−0.0106 (9)
C20	0.090 (2)	0.0684 (18)	0.0523 (15)	0.0027 (15)	−0.0249 (14)	−0.0146 (14)
C21	0.0389 (11)	0.0392 (12)	0.0330 (11)	−0.0012 (10)	−0.0040 (9)	−0.0089 (9)
C22	0.0668 (16)	0.0670 (17)	0.0387 (13)	−0.0280 (14)	−0.0050 (11)	−0.0115 (12)
C23	0.0729 (17)	0.0674 (17)	0.0386 (13)	−0.0267 (14)	0.0006 (12)	−0.0069 (12)
C24	0.0595 (15)	0.0525 (14)	0.0338 (11)	0.0004 (12)	−0.0067 (10)	−0.0087 (11)
C25	0.0627 (16)	0.0808 (19)	0.0467 (14)	−0.0232 (15)	−0.0142 (12)	−0.0151 (13)
C26	0.0587 (15)	0.0747 (18)	0.0430 (13)	−0.0280 (14)	−0.0049 (11)	−0.0096 (13)
Cl2	0.0529 (4)	0.0598 (4)	0.0614 (4)	0.0131 (3)	−0.0138 (3)	−0.0083 (3)
N1	0.0444 (10)	0.0417 (10)	0.0368 (9)	0.0045 (8)	−0.0088 (8)	−0.0134 (8)
N2	0.0524 (11)	0.0383 (10)	0.0408 (10)	0.0047 (9)	−0.0107 (8)	−0.0148 (8)

C1—N1	1.369 (2)	C13—H13	0.9300
C1—C2	1.408 (3)	C14—C15	1.393 (3)
C1—C6	1.415 (3)	C14—H14	0.9300
C2—C3	1.361 (3)	C15—C16	1.378 (3)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.394 (3)	C16—C17	1.400 (3)
C3—H3	0.9300	C16—C20	1.499 (3)
C4—C5	1.362 (3)	C17—N2	1.375 (2)
C4—Cl2	1.742 (2)	C18—N2	1.378 (2)
C5—C6	1.416 (3)	C18—C19	1.450 (3)
C5—H5	0.9300	C19—N1	1.315 (2)
C6—C7	1.428 (3)	C20—H20A	0.9600
C7—C8	1.375 (3)	C20—H20B	0.9600
C7—C21	1.495 (3)	C20—H20C	0.9600
C8—C19	1.430 (3)	C21—C26	1.368 (3)
C8—C9	1.509 (3)	C21—C22	1.377 (3)
C9—C10	1.530 (3)	C22—C23	1.375 (3)
C9—H9A	0.9700	C22—H22	0.9300
C9—H9B	0.9700	C23—C24	1.368 (3)
C10—C11	1.492 (3)	C23—H23	0.9300
C10—H10A	0.9700	C24—C25	1.355 (3)
C10—H10B	0.9700	C24—H24	0.9300
C11—C18	1.364 (3)	C25—C26	1.388 (3)
C11—C12	1.432 (3)	C25—H25	0.9300
C12—C13	1.400 (3)	C26—H26	0.9300
C12—C17	1.410 (3)	N2—H2A	0.8600
C13—C14	1.369 (3)
N1—C1—C2	118.08 (18)	C13—C14—H14	119.3
N1—C1—C6	122.72 (18)	C15—C14—H14	119.3
C2—C1—C6	119.20 (18)	C16—C15—C14	122.7 (2)
C3—C2—C1	121.0 (2)	C16—C15—H15	118.6
C3—C2—H2	119.5	C14—C15—H15	118.6
C1—C2—H2	119.5	C15—C16—C17	115.4 (2)
C2—C3—C4	119.4 (2)	C15—C16—C20	123.0 (2)
C2—C3—H3	120.3	C17—C16—C20	121.6 (2)
C4—C3—H3	120.3	N2—C17—C16	128.9 (2)
C5—C4—C3	121.83 (19)	N2—C17—C12	108.05 (17)
C5—C4—Cl2	119.76 (16)	C16—C17—C12	123.0 (2)
C3—C4—Cl2	118.41 (16)	C11—C18—N2	110.36 (18)
C4—C5—C6	119.80 (18)	C11—C18—C19	123.91 (18)
C4—C5—H5	120.1	N2—C18—C19	124.99 (18)
C6—C5—H5	120.1	N1—C19—C8	125.10 (18)
C1—C6—C5	118.68 (18)	N1—C19—C18	118.81 (18)
C1—C6—C7	118.34 (18)	C8—C19—C18	116.00 (18)
C5—C6—C7	122.98 (18)	C16—C20—H20A	109.5
C8—C7—C6	118.72 (17)	C16—C20—H20B	109.5
C8—C7—C21	121.44 (18)	H20A—C20—H20B	109.5
C6—C7—C21	119.80 (17)	C16—C20—H20C	109.5
C7—C8—C19	118.02 (18)	H20A—C20—H20C	109.5
C7—C8—C9	123.77 (18)	H20B—C20—H20C	109.5
C19—C8—C9	118.14 (18)	C26—C21—C22	117.98 (19)
C8—C9—C10	114.34 (18)	C26—C21—C7	121.54 (19)
C8—C9—H9A	108.7	C22—C21—C7	120.48 (18)
C10—C9—H9A	108.7	C23—C22—C21	121.5 (2)
C8—C9—H9B	108.7	C23—C22—H22	119.3
C10—C9—H9B	108.7	C21—C22—H22	119.3
H9A—C9—H9B	107.6	C24—C23—C22	119.8 (2)
C11—C10—C9	109.85 (18)	C24—C23—H23	120.1
C11—C10—H10A	109.7	C22—C23—H23	120.1
C9—C10—H10A	109.7	C25—C24—C23	119.5 (2)
C11—C10—H10B	109.7	C25—C24—H24	120.3
C9—C10—H10B	109.7	C23—C24—H24	120.3
H10A—C10—H10B	108.2	C24—C25—C26	120.7 (2)
C18—C11—C12	106.56 (18)	C24—C25—H25	119.6
C18—C11—C10	121.04 (18)	C26—C25—H25	119.6
C12—C11—C10	132.23 (19)	C21—C26—C25	120.5 (2)
C13—C12—C17	118.90 (19)	C21—C26—H26	119.7
C13—C12—C11	134.2 (2)	C25—C26—H26	119.7
C17—C12—C11	106.81 (18)	C19—N1—C1	117.09 (17)
C14—C13—C12	118.4 (2)	C17—N2—C18	108.15 (17)
C14—C13—H13	120.8	C17—N2—H2A	125.9
C12—C13—H13	120.8	C18—N2—H2A	125.9
C13—C14—C15	121.4 (2)
N1—C1—C2—C3	179.8 (2)	C15—C16—C17—C12	2.6 (3)
C6—C1—C2—C3	0.5 (3)	C20—C16—C17—C12	−178.5 (2)
C1—C2—C3—C4	−0.2 (3)	C13—C12—C17—N2	175.20 (18)
C2—C3—C4—C5	−0.3 (3)	C11—C12—C17—N2	−2.2 (2)
C2—C3—C4—Cl2	179.24 (18)	C13—C12—C17—C16	−3.4 (3)
C3—C4—C5—C6	0.6 (3)	C11—C12—C17—C16	179.2 (2)
Cl2—C4—C5—C6	−178.99 (15)	C12—C11—C18—N2	−2.4 (2)
N1—C1—C6—C5	−179.55 (18)	C10—C11—C18—N2	−178.18 (18)
C2—C1—C6—C5	−0.2 (3)	C12—C11—C18—C19	168.12 (19)
N1—C1—C6—C7	0.3 (3)	C10—C11—C18—C19	−7.7 (3)
C2—C1—C6—C7	179.7 (2)	C7—C8—C19—N1	0.0 (3)
C4—C5—C6—C1	−0.3 (3)	C9—C8—C19—N1	−177.1 (2)
C4—C5—C6—C7	179.8 (2)	C7—C8—C19—C18	−176.48 (18)
C1—C6—C7—C8	−1.3 (3)	C9—C8—C19—C18	6.4 (3)
C5—C6—C7—C8	178.57 (19)	C11—C18—C19—N1	−159.1 (2)
C1—C6—C7—C21	176.41 (18)	N2—C18—C19—N1	10.0 (3)
C5—C6—C7—C21	−3.7 (3)	C11—C18—C19—C8	17.6 (3)
C6—C7—C8—C19	1.1 (3)	N2—C18—C19—C8	−173.25 (19)
C21—C7—C8—C19	−176.52 (18)	C8—C7—C21—C26	−103.4 (3)
C6—C7—C8—C9	178.06 (19)	C6—C7—C21—C26	78.9 (3)
C21—C7—C8—C9	0.4 (3)	C8—C7—C21—C22	77.4 (3)
C7—C8—C9—C10	144.9 (2)	C6—C7—C21—C22	−100.2 (2)
C19—C8—C9—C10	−38.2 (3)	C26—C21—C22—C23	−0.3 (4)
C8—C9—C10—C11	45.2 (3)	C7—C21—C22—C23	178.9 (2)
C9—C10—C11—C18	−24.0 (3)	C21—C22—C23—C24	0.0 (4)
C9—C10—C11—C12	161.5 (2)	C22—C23—C24—C25	0.5 (4)
C18—C11—C12—C13	−174.0 (2)	C23—C24—C25—C26	−0.8 (4)
C10—C11—C12—C13	1.1 (4)	C22—C21—C26—C25	0.0 (4)
C18—C11—C12—C17	2.8 (2)	C7—C21—C26—C25	−179.2 (2)
C10—C11—C12—C17	177.9 (2)	C24—C25—C26—C21	0.6 (4)
C17—C12—C13—C14	1.3 (3)	C8—C19—N1—C1	−1.0 (3)
C11—C12—C13—C14	177.8 (2)	C18—C19—N1—C1	175.42 (17)
C12—C13—C14—C15	1.3 (4)	C2—C1—N1—C19	−178.57 (19)
C13—C14—C15—C16	−2.1 (4)	C6—C1—N1—C19	0.8 (3)
C14—C15—C16—C17	0.1 (4)	C16—C17—N2—C18	179.2 (2)
C14—C15—C16—C20	−178.7 (2)	C12—C17—N2—C18	0.8 (2)
C15—C16—C17—N2	−175.6 (2)	C11—C18—N2—C17	1.1 (2)
C20—C16—C17—N2	3.2 (4)	C19—C18—N2—C17	−169.34 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···Cg1i	0.97	2.96	3.848 (3)	152
C26—H26···Cg2i	0.93	2.51	3.391 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the ring C1–C6 and Cg2 is the centroid of the indole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯Cg1i	0.97	2.96	3.848 (3)	152
C26—H26⋯Cg2i	0.93	2.51	3.391 (3)	158

Symmetry code: (i) .