10-Methyl-2-oxo-4-phenyl-2,11-di­hydro­pyrano[2,3-a]carbazole-3-carbo­nitrile

Thiruvalluvar, A.; Yamuna, E.; Archana, R.; Rajendra Prasad, K.J.; Butcher, R.J.

doi:10.1107/S1600536813011823

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o831

doi:10.1107/S1600536813011823

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10-Methyl-2-oxo-4-phenyl-2,11-dihydropyrano[2,3-a]carbazole-3-carbonitrile

A. Thiruvalluvar,^a ^* E. Yamuna,^b R. Archana,^a K. J. Rajendra Prasad ^c and R. J. Butcher ^d

^aPostgraduate Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, ^bDepartment of Chemistry, Tamkang University, Tamsui 25137, Taiwan, ^cDepartment of Chemistry, Bharathiar University, Coimbatore 641 046, Tamilnadu, India, and ^dDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: thiruvalluvar.a@gmail.com

(Received 27 April 2013; accepted 30 April 2013; online 4 May 2013)

In the title molecule, 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 R₂²(14) loops and a C—H⋯N interaction is also found. Molecules 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_r = 350.36
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.053
wR(F²) = 0.154
S = 1.16
8485 reflections
249 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.31 e Å⁻³

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) -x+2, -y+1, -z; (ii) $[-x+{\script{7\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813011823/sj5318sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813011823/sj5318Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536813011823/sj5318Isup4.cml

checkCIF report

Comment top

The title compound has been analysed as part of our crystallographic studies on pyranocarbazoles. Sridharan et al. (2009), have reported the synthesis and X-ray crystal structure of a related pyranocarbazole.

In the title molecule (Scheme I, Fig. 1), C₂₃H₁₄N₂O₂, the atoms in the carbazole unit deviate from planarity [maximum deviation from mean plane = -0.1018 (8) Å for atom C4A]. 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.

Intermolecular N11—H11···O2 hydrogen bonds form a R²₂(14) (Bernstein et al., 1995) ring in the crystal structure and a C43—H43···N31 interaction is also found (Table 1, Fig. 2). Molecules are further linked by five π-π [Cg1—Cg4ⁱ = 3.7068 (6), Cg2—Cg4ⁱⁱ = Cg4—Cg2ⁱⁱⁱ = 3.5702 (5), Cg4—Cg1ⁱ = 3.7067 (6) and Cg4—Cg4ⁱ = 3.5927 (6) Å, symmetry code (i): 1 - x, 2 - y, - z, (ii): 1 + x, y, z, (iii): - 1 + x, y, z where Cg1, Cg2 and Cg4 are the centroids of the pyrrole (N11/C11A/C6A/C6B/C10A), pyran (O1/C2/C3/C4/C4A/C11B) and benzene (C6B/C7—C10/C10A) rings, respectively (Fig. 3)] interactions to form a three-dimensional network.

Related literature top

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

Experimental top

A mixture of benzaldehyde (0.106 g, 1 mmol), malononitrile (0.080 g, 1.2 mmol), 8-methyl-9H-carbazol-1-ol (0.197 g, 1 mmol) and NaHCO₃ (0.084 g, 2 mmol) was ground at room temperature with the mortar and pestle. The reaction was monitored by TLC. After the completion of the reaction, the mixture was poured into water and then filtered. The obtained crude product was purified by silica gel column chromatography using petroleum ether: ethyl acetate (98:2) yielded the title compound (0.308 g, 88%). Then this pure compound was recrystallized from EtOAc.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. The partial packing of the title compound, viewed down the b axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.
	Fig. 3. The crystal structure of compound, showing the formation of π-π stacking interactions.

10-Methyl-2-oxo-4-phenyl-2,11-dihydropyrano[2,3-a]carbazole-3-carbonitrile top

Crystal data top

C₂₃H₁₄N₂O₂	F(000) = 728
M_r = 350.36	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0629P)² + 0.6142P] where P = (F_o² + 2F_c²)/3
8485 reflections	(Δ/σ)_max = 0.001
249 parameters	Δρ_max = 0.64 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₃H₁₄N₂O₂	V = 1665.17 (4) Å³
M_r = 350.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.8659 (1) Å	µ = 0.09 mm⁻¹
b = 8.5151 (1) Å	T = 123 K
c = 25.1137 (4) Å	0.46 × 0.41 × 0.29 mm
β = 98.133 (2)°

Data collection top

Agilent Xcalibur Ruby Gemini diffractometer	8485 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	7184 reflections with I > 2σ(I)
T_min = 0.978, T_max = 1.000	R_int = 0.022
27185 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	Δρ_max = 0.64 e Å⁻³
8485 reflections	Δρ_min = −0.31 e Å⁻³
249 parameters

Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+1, −z; (ii) −x+7/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₄N₂O₂
M_r	350.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	123
a, b, c (Å)	7.8659 (1), 8.5151 (1), 25.1137 (4)
β (°)	98.133 (2)
V (Å³)	1665.17 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.46 × 0.41 × 0.29

Data collection
Diffractometer	Agilent Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.978, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	27185, 8485, 7184
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.860

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.154, 1.16
No. of reflections	8485
No. of parameters	249
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.31

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009), SHELXL2013 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+1, −z; (ii) −x+7/2, y+1/2, −z+1/2.

Acknowledgements

RJB acknowledges the NSF–MRI program (grant No. CHE0619278) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sridharan, M., Rajendra Prasad, K. J., Thomas Gunaseelan, A., Thiruvalluvar, A. & Butcher, R. J. (2009). Acta Cryst. E65, o830. Web of Science CSD CrossRef IUCr Journals Google Scholar