10-Methyl-2-oxo-4-phenyl-2,11-di-hydro-pyrano[2,3-a]carbazole-3-carbo-nitrile.

In the title mol-ecule, C23H14N2O2, the atoms in the carbazole unit deviate from planarity [maximum deviation from mean plane = 0.1018 (8) Å]. The pyrrole ring makes dihedral angles of 4.44 (5), 3.84 (5), 2.18 (5) and 56.44 (5)° with the pyran, fused benzene rings and phenyl ring, respectively. In the crystal, pairs of N-H⋯O hydrogen bonds generate R 2 (2)(14) loops and a C-H⋯N inter-action is also found. Mol-ecules are further linked by a number of π-π interactions [centroid-centroid distances vary from 3.5702 (5) to 3.7068 (6) Å], forming a three-dimensional network.

Related literature

For a related structure, see: Sridharan et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C23H14N2O2

M = 350.36

Monoclinic,

a = 7.8659 (1) Å

b = 8.5151 (1) Å

c = 25.1137 (4) Å

β = 98.133 (2)°

V = 1665.17 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 123 K

0.46 × 0.41 × 0.29 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.978, T max = 1.000

27185 measured reflections

8485 independent reflections

7184 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.154

S = 1.16

8485 reflections

249 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.64 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL2013 and PLATON.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813011823/sj5318sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011823/sj5318Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813011823/sj5318Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813011823/sj5318Isup4.cml

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

C23H14N2O2	F(000) = 728
Mr = 350.36	Dx = 1.398 Mg m−3
Monoclinic, P21/n	Melting point: 573 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.8659 (1) Å	Cell parameters from 11879 reflections
b = 8.5151 (1) Å	θ = 3.3–37.6°
c = 25.1137 (4) Å	µ = 0.09 mm−1
β = 98.133 (2)°	T = 123 K
V = 1665.17 (4) Å3	Prism, colourless
Z = 4	0.46 × 0.41 × 0.29 mm

Agilent Xcalibur Ruby Gemini diffractometer	8485 independent reflections
Radiation source: Enhance (Mo) X-ray Source	7184 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 10.5081 pixels mm-1	θmax = 37.7°, θmin = 3.3°
ω scans	h = −12→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −14→11
Tmin = 0.978, Tmax = 1.000	l = −33→42
27185 measured reflections

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: mixed
wR(F2) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ2(Fo2) + (0.0629P)2 + 0.6142P] where P = (Fo2 + 2Fc2)/3
8485 reflections	(Δ/σ)max = 0.001
249 parameters	Δρmax = 0.64 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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

	x	y	z	Uiso*/Ueq
O1	1.01566 (8)	0.60784 (8)	0.06827 (3)	0.0167 (2)
O2	1.22719 (10)	0.44963 (10)	0.05318 (3)	0.0242 (2)
N11	0.66938 (9)	0.73028 (9)	0.03766 (3)	0.0157 (2)
N31	1.57295 (15)	0.47611 (18)	0.15540 (5)	0.0423 (4)
C2	1.17839 (11)	0.55044 (11)	0.08165 (4)	0.0171 (2)
C3	1.27720 (11)	0.61006 (11)	0.13093 (4)	0.0172 (2)
C4	1.21143 (10)	0.71613 (11)	0.16390 (4)	0.0155 (2)
C4A	1.04339 (10)	0.78085 (10)	0.14642 (4)	0.0151 (2)
C5	0.97078 (11)	0.90356 (11)	0.17439 (4)	0.0177 (2)
C6	0.80984 (11)	0.96194 (11)	0.15617 (4)	0.0183 (2)
C6A	0.71503 (10)	0.89666 (10)	0.10970 (4)	0.0156 (2)
C6B	0.54287 (10)	0.92067 (10)	0.08278 (4)	0.0160 (2)
C7	0.40849 (12)	1.01896 (12)	0.09342 (4)	0.0203 (2)
C8	0.25297 (12)	1.00848 (13)	0.06019 (4)	0.0228 (2)
C9	0.23100 (12)	0.90200 (12)	0.01695 (4)	0.0213 (2)
C10	0.36192 (11)	0.80389 (11)	0.00460 (4)	0.0178 (2)
C10A	0.51917 (10)	0.81560 (10)	0.03876 (4)	0.0155 (2)
C11	0.33434 (14)	0.69327 (13)	−0.04214 (4)	0.0243 (2)
C11A	0.78675 (10)	0.77783 (10)	0.08058 (4)	0.0145 (2)
C11B	0.95174 (10)	0.72217 (10)	0.09862 (4)	0.0144 (2)
C31	1.44170 (13)	0.53773 (14)	0.14491 (4)	0.0252 (3)
C41	1.30970 (11)	0.76005 (11)	0.21667 (4)	0.0171 (2)
C42	1.47693 (12)	0.81736 (14)	0.21961 (4)	0.0231 (2)
C43	1.57064 (13)	0.85772 (15)	0.26898 (5)	0.0265 (3)
C44	1.49880 (14)	0.83808 (14)	0.31591 (4)	0.0249 (3)
C45	1.33329 (14)	0.77825 (13)	0.31351 (4)	0.0234 (2)
C46	1.23742 (12)	0.74058 (12)	0.26415 (4)	0.0203 (2)
H5	1.03437	0.94587	0.20613	0.0213*
H6	0.76336	1.04525	0.17474	0.0220*
H7	0.42394	1.09075	0.12266	0.0244*
H8	0.16011	1.07380	0.06663	0.0273*
H9	0.12208	0.89666	−0.00482	0.0256*
H11	0.689 (2)	0.667 (2)	0.0118 (8)	0.035 (5)*
H11A	0.22112	0.64398	−0.04383	0.0365*
H11B	0.42344	0.61199	−0.03771	0.0365*
H11C	0.34041	0.75140	−0.07550	0.0365*
H42	1.52737	0.82897	0.18763	0.0277*
H43	1.68358	0.89864	0.27051	0.0318*
H44	1.56251	0.86544	0.34963	0.0299*
H45	1.28523	0.76294	0.34576	0.0282*
H46	1.12358	0.70188	0.26270	0.0243*

	U11	U22	U33	U12	U13	U23
O1	0.0135 (2)	0.0198 (3)	0.0159 (3)	0.0031 (2)	−0.0012 (2)	−0.0034 (2)
O2	0.0225 (3)	0.0288 (4)	0.0201 (3)	0.0093 (3)	−0.0006 (3)	−0.0063 (3)
N11	0.0131 (3)	0.0170 (3)	0.0161 (3)	0.0010 (2)	−0.0014 (2)	−0.0017 (2)
N31	0.0271 (5)	0.0631 (8)	0.0330 (6)	0.0232 (5)	−0.0089 (4)	−0.0117 (5)
C2	0.0142 (3)	0.0206 (4)	0.0159 (3)	0.0032 (3)	0.0001 (3)	−0.0008 (3)
C3	0.0126 (3)	0.0228 (4)	0.0153 (3)	0.0029 (3)	−0.0011 (2)	−0.0010 (3)
C4	0.0117 (3)	0.0198 (3)	0.0145 (3)	−0.0008 (2)	0.0000 (2)	−0.0004 (3)
C4A	0.0113 (3)	0.0179 (3)	0.0155 (3)	−0.0007 (2)	−0.0001 (2)	−0.0016 (3)
C5	0.0137 (3)	0.0196 (4)	0.0190 (4)	−0.0004 (3)	−0.0005 (3)	−0.0045 (3)
C6	0.0143 (3)	0.0198 (4)	0.0202 (4)	0.0004 (3)	0.0004 (3)	−0.0051 (3)
C6A	0.0124 (3)	0.0171 (3)	0.0169 (3)	0.0003 (2)	0.0003 (2)	−0.0015 (3)
C6B	0.0125 (3)	0.0174 (3)	0.0177 (3)	0.0012 (3)	0.0006 (3)	−0.0002 (3)
C7	0.0156 (3)	0.0235 (4)	0.0215 (4)	0.0045 (3)	0.0012 (3)	−0.0015 (3)
C8	0.0152 (3)	0.0269 (4)	0.0254 (4)	0.0054 (3)	0.0002 (3)	0.0007 (3)
C9	0.0140 (3)	0.0257 (4)	0.0229 (4)	0.0022 (3)	−0.0022 (3)	0.0025 (3)
C10	0.0144 (3)	0.0199 (4)	0.0179 (4)	−0.0007 (3)	−0.0018 (3)	0.0017 (3)
C10A	0.0125 (3)	0.0167 (3)	0.0165 (3)	0.0004 (2)	−0.0002 (2)	0.0011 (3)
C11	0.0231 (4)	0.0252 (4)	0.0226 (4)	−0.0012 (3)	−0.0039 (3)	−0.0029 (3)
C11A	0.0117 (3)	0.0162 (3)	0.0149 (3)	0.0000 (2)	−0.0003 (2)	−0.0006 (3)
C11B	0.0121 (3)	0.0157 (3)	0.0151 (3)	0.0003 (2)	0.0006 (2)	−0.0013 (3)
C31	0.0183 (4)	0.0356 (5)	0.0200 (4)	0.0082 (3)	−0.0028 (3)	−0.0046 (4)
C41	0.0136 (3)	0.0217 (4)	0.0150 (3)	−0.0001 (3)	−0.0010 (3)	−0.0007 (3)
C42	0.0145 (3)	0.0359 (5)	0.0179 (4)	−0.0040 (3)	−0.0011 (3)	−0.0015 (3)
C43	0.0177 (4)	0.0372 (5)	0.0222 (4)	−0.0034 (3)	−0.0050 (3)	−0.0028 (4)
C44	0.0261 (4)	0.0281 (5)	0.0180 (4)	0.0025 (3)	−0.0055 (3)	−0.0032 (3)
C45	0.0292 (4)	0.0256 (4)	0.0150 (4)	0.0006 (3)	0.0013 (3)	−0.0006 (3)
C46	0.0201 (4)	0.0236 (4)	0.0170 (4)	−0.0016 (3)	0.0024 (3)	−0.0006 (3)

O1—C2	1.3670 (11)	C10—C10A	1.4056 (13)
O1—C11B	1.3748 (11)	C10—C11	1.4967 (14)
O2—C2	1.2137 (12)	C11A—C11B	1.3956 (12)
N11—C10A	1.3906 (11)	C41—C46	1.4016 (14)
N11—C11A	1.3772 (12)	C41—C42	1.3952 (13)
N31—C31	1.1548 (17)	C42—C43	1.3929 (16)
N11—H11	0.874 (18)	C43—C44	1.3874 (16)
C2—C3	1.4565 (14)	C44—C45	1.3914 (16)
C3—C4	1.3748 (13)	C45—C46	1.3942 (14)
C3—C31	1.4312 (14)	C5—H5	0.9500
C4—C41	1.4845 (14)	C6—H6	0.9500
C4—C4A	1.4420 (12)	C7—H7	0.9500
C4A—C5	1.4230 (13)	C8—H8	0.9500
C4A—C11B	1.4020 (13)	C9—H9	0.9500
C5—C6	1.3767 (13)	C11—H11A	0.9800
C6—C6A	1.4074 (14)	C11—H11B	0.9800
C6A—C6B	1.4400 (12)	C11—H11C	0.9800
C6A—C11A	1.4120 (12)	C42—H42	0.9500
C6B—C10A	1.4139 (13)	C43—H43	0.9500
C6B—C7	1.4032 (13)	C44—H44	0.9500
C7—C8	1.3828 (14)	C45—H45	0.9500
C8—C9	1.4064 (14)	C46—H46	0.9500
C9—C10	1.3946 (13)
C2—O1—C11B	121.34 (8)	O1—C11B—C4A	122.89 (7)
C10A—N11—C11A	107.95 (7)	C4A—C11B—C11A	119.92 (8)
C11A—N11—H11	126.4 (11)	N31—C31—C3	178.26 (13)
C10A—N11—H11	125.2 (11)	C4—C41—C42	120.22 (8)
O1—C2—C3	116.93 (8)	C42—C41—C46	119.29 (9)
O2—C2—C3	124.88 (9)	C4—C41—C46	120.47 (8)
O1—C2—O2	118.12 (9)	C41—C42—C43	120.64 (9)
C4—C3—C31	122.63 (9)	C42—C43—C44	119.91 (10)
C2—C3—C4	122.66 (8)	C43—C44—C45	119.90 (10)
C2—C3—C31	114.44 (8)	C44—C45—C46	120.52 (9)
C4A—C4—C41	120.97 (8)	C41—C46—C45	119.72 (9)
C3—C4—C4A	118.33 (9)	C4A—C5—H5	119.00
C3—C4—C41	120.69 (8)	C6—C5—H5	119.00
C4—C4A—C5	123.02 (9)	C5—C6—H6	120.00
C4—C4A—C11B	117.56 (8)	C6A—C6—H6	120.00
C5—C4A—C11B	119.39 (8)	C6B—C7—H7	121.00
C4A—C5—C6	121.03 (9)	C8—C7—H7	121.00
C5—C6—C6A	119.17 (8)	C7—C8—H8	120.00
C6B—C6A—C11A	106.06 (8)	C9—C8—H8	120.00
C6—C6A—C6B	133.32 (8)	C8—C9—H9	119.00
C6—C6A—C11A	120.59 (8)	C10—C9—H9	119.00
C6A—C6B—C10A	106.77 (7)	C10—C11—H11A	109.00
C6A—C6B—C7	132.76 (9)	C10—C11—H11B	109.00
C7—C6B—C10A	120.45 (8)	C10—C11—H11C	109.00
C6B—C7—C8	118.20 (9)	H11A—C11—H11B	109.00
C7—C8—C9	120.61 (9)	H11A—C11—H11C	109.00
C8—C9—C10	122.95 (9)	H11B—C11—H11C	109.00
C9—C10—C11	121.45 (9)	C41—C42—H42	120.00
C10A—C10—C11	122.73 (8)	C43—C42—H42	120.00
C9—C10—C10A	115.82 (9)	C42—C43—H43	120.00
C6B—C10A—C10	121.97 (8)	C44—C43—H43	120.00
N11—C10A—C6B	109.13 (7)	C43—C44—H44	120.00
N11—C10A—C10	128.88 (8)	C45—C44—H44	120.00
C6A—C11A—C11B	119.77 (9)	C44—C45—H45	120.00
N11—C11A—C11B	130.08 (8)	C46—C45—H45	120.00
N11—C11A—C6A	110.08 (7)	C41—C46—H46	120.00
O1—C11B—C11A	117.18 (8)	C45—C46—H46	120.00
C11B—O1—C2—O2	−179.96 (9)	C6—C6A—C6B—C10A	−177.82 (10)
C11B—O1—C2—C3	3.08 (12)	C11A—C6A—C6B—C7	178.07 (10)
C2—O1—C11B—C4A	−3.74 (13)	C11A—C6A—C6B—C10A	−0.10 (10)
C2—O1—C11B—C11A	177.50 (8)	C6—C6A—C11A—N11	178.70 (8)
C11A—N11—C10A—C6B	0.83 (10)	C6—C6A—C11A—C11B	1.36 (13)
C11A—N11—C10A—C10	−177.20 (9)	C6B—C6A—C11A—N11	0.62 (10)
C10A—N11—C11A—C6A	−0.91 (10)	C6B—C6A—C11A—C11B	−176.72 (8)
C10A—N11—C11A—C11B	176.08 (9)	C6A—C6B—C7—C8	−177.19 (10)
O1—C2—C3—C4	1.63 (14)	C10A—C6B—C7—C8	0.78 (14)
O1—C2—C3—C31	175.76 (8)	C6A—C6B—C10A—N11	−0.45 (10)
O2—C2—C3—C4	−175.11 (10)	C6A—C6B—C10A—C10	177.75 (8)
O2—C2—C3—C31	−0.98 (14)	C7—C6B—C10A—N11	−178.89 (8)
C2—C3—C4—C4A	−5.55 (14)	C7—C6B—C10A—C10	−0.70 (14)
C2—C3—C4—C41	173.15 (9)	C6B—C7—C8—C9	−0.04 (15)
C31—C3—C4—C4A	−179.20 (9)	C7—C8—C9—C10	−0.85 (16)
C31—C3—C4—C41	−0.50 (14)	C8—C9—C10—C10A	0.92 (14)
C3—C4—C4A—C5	−173.02 (9)	C8—C9—C10—C11	−179.30 (10)
C3—C4—C4A—C11B	4.82 (13)	C9—C10—C10A—N11	177.66 (9)
C41—C4—C4A—C5	8.28 (14)	C9—C10—C10A—C6B	−0.15 (13)
C41—C4—C4A—C11B	−173.88 (8)	C11—C10—C10A—N11	−2.12 (15)
C3—C4—C41—C42	54.88 (13)	C11—C10—C10A—C6B	−179.93 (9)
C3—C4—C41—C46	−123.43 (10)	N11—C11A—C11B—O1	4.06 (14)
C4A—C4—C41—C42	−126.45 (10)	N11—C11A—C11B—C4A	−174.74 (9)
C4A—C4—C41—C46	55.24 (13)	C6A—C11A—C11B—O1	−179.21 (8)
C4—C4A—C5—C6	179.91 (9)	C6A—C11A—C11B—C4A	2.00 (13)
C11B—C4A—C5—C6	2.10 (14)	C4—C41—C42—C43	−179.49 (10)
C4—C4A—C11B—O1	−0.34 (13)	C46—C41—C42—C43	−1.16 (16)
C4—C4A—C11B—C11A	178.38 (8)	C4—C41—C46—C45	178.19 (9)
C5—C4A—C11B—O1	177.59 (8)	C42—C41—C46—C45	−0.14 (15)
C5—C4A—C11B—C11A	−3.69 (13)	C41—C42—C43—C44	1.27 (18)
C4A—C5—C6—C6A	1.22 (14)	C42—C43—C44—C45	−0.06 (19)
C5—C6—C6A—C6B	174.51 (10)	C43—C44—C45—C46	−1.25 (17)
C5—C6—C6A—C11A	−2.95 (14)	C44—C45—C46—C41	1.34 (16)
C6—C6A—C6B—C7	0.35 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O2i	0.874 (18)	2.095 (19)	2.9561 (11)	168.2 (15)
C43—H43···N31ii	0.95	2.56	3.3130 (17)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11⋯O2i	0.874 (18)	2.095 (19)	2.9561 (11)	168.2 (15)
C43—H43⋯N31ii	0.95	2.56	3.3130 (17)	136

Symmetry codes: (i) ; (ii) .