4′-Cyano­biphenyl-4-yl 7-diethyl­amino-2-oxo-2H-chromene-3-carboxyl­ate

Sreenivasa, S.; Srinivasa, H.T.; Palakshamurthy, B.S.; Kumar, V.; Devarajegowda, H.C.

doi:10.1107/S1600536813001591

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o266

doi:10.1107/S1600536813001591

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4′-Cyanobiphenyl-4-yl 7-diethylamino-2-oxo-2H-chromene-3-carboxylate

S. Sreenivasa,^a H. T. Srinivasa,^b B. S. Palakshamurthy,^c Vijith Kumar ^d and H. C. Devarajegowda ^c ^*

^aDeapartment of Studies and Research in Chemistry, Tumkur University, Tumkur 572 103, Karnataka, India, ^bRaman Research Institute, C. V. Raman Avenue, Sadashivanagar, Bangalore 560 080, Karnataka, India, ^cDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, and ^dSoild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 10 January 2013; accepted 16 January 2013; online 19 January 2013)

In the title compound, C₂₇H₂₂N₂O₄, the dihedral angles between the central benzene ring and the cyanobenzene ring and the 2H-coumarin ring system (r.m.s. deviation = 0.014 Å) are 22.95 (11) and 75.59 (8)°, respectively. Both terminal C atoms of the pendant diethylamino group lie to the same side of the coumarin ring system [deviations = 1.366 (2) and 1.266 (2) Å]. In the crystal, molecules are linked by C—H⋯O and C—H⋯N hydrogen bonds and a C—H⋯π interaction, generating a three-dimensional network.

Related literature

For the biological properties of coumarin derivatives, see: Bhat et al. (2006 ); Chimichi et al. (2002 ).

Experimental

Crystal data

C₂₇H₂₂N₂O₄
M_r = 438.47
Triclinic, $[P \overline 1]$
a = 9.652 (3) Å
b = 10.252 (4) Å
c = 11.121 (4) Å
α = 87.214 (10)°
β = 86.358 (10)°
γ = 84.348 (11)°
V = 1091.9 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 300 K
0.24 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.979, T_max = 0.984
10667 measured reflections
3783 independent reflections
2495 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.173
S = 0.97
3783 reflections
301 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1ⁱ	0.93	2.53	3.446 (3)	170
C11—H11⋯N2ⁱⁱ	0.93	2.59	3.435 (3)	152
C16—H16⋯O1ⁱⁱⁱ	0.93	2.54	3.465 (3)	177
C1—H1B⋯Cg3^iv	0.96	2.82	3.626 (3)	142
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x-1, -y+2, -z+1; (iii) -x, -y+2, -z+2; (iv) x+1, y-1, z.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813001591/hb7027sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813001591/hb7027Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813001591/hb7027Isup3.cml

checkCIF report

Comment top

Coumarins are well known for displaying a broad range of biological activities like anti- inflammatory, anticonvulsant (Bhat et al., 2006) and antitumor agents (Chimichi et al., 2002). As part of our studies in this area, we now report the synthesis and crystal structure (Fig. 1) of the title cyanobiphenyl coumarin, (I), derived from the reaction of 7-diethylamino coumarin.

The 2H-chromene ring (O2/C5–C13) system in (I) is almost planar, with a maximum deviation of 0.025 (2) Å for atom C13. The dihedral angle between 2H-chromene ring (O2/C5–C13) with the benzene(C15–C20) terminal benzene(C21—C26) rings are 75.59 (8)° and 56.02 (1)° respectively. The crystal structure is characterized by intermolecular C6—H6···O1, C11—H11···N2 and C16—H16···O1 hydrogen bonding and also features C—H..π [C_g(3)(C15–C20) interactions (Table.1). Crystal packing for the title compound with hydrogen bonds drawn as dashed lines (Fig. 2).

Related literature top

For the biological properties of coumarin derivatives, see: Bhat et al. (2006); Chimichi et al. (2002).

Experimental top

N,N-Dicyclohexylcarbodiimide (215 mg, 1.2 mmol) was added to a magnetically stirred solution of 7-(diethylamino) -2-oxo-2H-chromene -3-carboxylic acid (261 mg, 1 mmol), 4-cyano 4^'-hydroxybiphenyl (195 mg, 1 mmol) and a catalytic quantity of N,N-dimethylaminopyrimidine (DMAP) in dried dichloromethane. Resultant reaction mixture was stirred further for 24 h at room temperature. Pure compound was obtained by aqueous workup and column chromatography. Colourless prisms were obtained from chloroform solution on slow evaporation at room temperature (m.p. 541 K).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing for the title compound with hydrogen bonds drawn as dashed lines.

4'-Cyanobiphenyl-4-yl 7-diethylamino-2-oxo-2H-chromene-3-carboxylate top

Crystal data top

C₂₇H₂₂N₂O₄	Z = 2
M_r = 438.47	F(000) = 460
Triclinic, P1	D_x = 1.334 Mg m⁻³
Hall symbol: -P 1	Melting point: 541 K
a = 9.652 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.252 (4) Å	Cell parameters from 3783 reflections
c = 11.121 (4) Å	θ = 1.8–25.0°
α = 87.214 (10)°	µ = 0.09 mm⁻¹
β = 86.358 (10)°	T = 300 K
γ = 84.348 (11)°	Prism, colourless
V = 1091.9 (6) Å³	0.24 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD diffractometer	3783 independent reflections
Radiation source: fine-focus sealed tube	2495 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ω and ϕ scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→10
T_min = 0.979, T_max = 0.984	k = −12→12
10667 measured reflections	l = −13→13

Refinement top

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)] = 0.058	H-atom parameters constrained
wR(F²) = 0.173	w = 1/[σ²(F_o²) + (0.1107P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
3783 reflections	Δρ_max = 0.22 e Å⁻³
301 parameters	Δρ_min = −0.37 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (4)

Crystal data top

C₂₇H₂₂N₂O₄	γ = 84.348 (11)°
M_r = 438.47	V = 1091.9 (6) Å³
Triclinic, P1	Z = 2
a = 9.652 (3) Å	Mo Kα radiation
b = 10.252 (4) Å	µ = 0.09 mm⁻¹
c = 11.121 (4) Å	T = 300 K
α = 87.214 (10)°	0.24 × 0.20 × 0.18 mm
β = 86.358 (10)°

Data collection top

Bruker SMART CCD diffractometer	3783 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2495 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.984	R_int = 0.048
10667 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.173	H-atom parameters constrained
S = 0.97	Δρ_max = 0.22 e Å⁻³
3783 reflections	Δρ_min = −0.37 e Å⁻³
301 parameters

Special details top

Experimental. ¹H NMR (400Mz, TMS): δ 8.36(s, 1H), 7.44–7.65(m, 6H), 7.12–7.08(m, 3H), 6.34(m, 2H), 3.38(m, 4H), 1.10(m, 6H); Elemental analysis calculated for C₂₇H₂₂N₂O₄, C, 73.96; H, 5.06; N, 6.39; found C, 74.20; H, 5.32; N, 6.33.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

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

	x	y	z	U_iso*/U_eq
O1	0.24765 (18)	1.10054 (17)	0.94063 (14)	0.0535 (5)
O2	0.37525 (15)	0.91308 (15)	0.92731 (12)	0.0417 (4)
O3	−0.04165 (16)	0.96402 (16)	0.71953 (13)	0.0503 (5)
O4	−0.0195 (2)	1.1161 (2)	0.85320 (18)	0.0753 (6)
N1	0.68882 (19)	0.52702 (19)	0.90485 (16)	0.0457 (5)
N2	−1.0656 (2)	1.3764 (2)	0.4192 (2)	0.0641 (7)
C1	0.7967 (3)	0.4011 (3)	0.7316 (2)	0.0668 (8)
H1A	0.7313	0.4453	0.6782	0.100*
H1B	0.8213	0.3130	0.7068	0.100*
H1C	0.8789	0.4469	0.7291	0.100*
C2	0.7317 (3)	0.3978 (2)	0.8581 (2)	0.0493 (6)
H2A	0.6507	0.3485	0.8602	0.059*
H2B	0.7980	0.3515	0.9109	0.059*
C3	0.7847 (3)	0.5811 (3)	0.9826 (2)	0.0529 (7)
H3A	0.8333	0.5094	1.0280	0.064*
H3B	0.7308	0.6370	1.0399	0.064*
C4	0.8898 (3)	0.6584 (3)	0.9148 (2)	0.0656 (8)
H4A	0.9469	0.6026	0.8608	0.098*
H4B	0.9474	0.6927	0.9706	0.098*
H4C	0.8426	0.7296	0.8695	0.098*
C5	0.4066 (2)	0.7908 (2)	0.88368 (16)	0.0342 (5)
C6	0.5309 (2)	0.7249 (2)	0.91367 (18)	0.0393 (6)
H6	0.5901	0.7641	0.9607	0.047*
C7	0.5690 (2)	0.5977 (2)	0.87307 (18)	0.0383 (5)
C8	0.4763 (2)	0.5447 (2)	0.7979 (2)	0.0448 (6)
H8	0.4998	0.4617	0.7681	0.054*
C9	0.3544 (2)	0.6131 (2)	0.76906 (19)	0.0425 (6)
H9	0.2965	0.5757	0.7195	0.051*
C10	0.3130 (2)	0.7385 (2)	0.81176 (17)	0.0361 (5)
C11	0.1893 (2)	0.8156 (2)	0.78679 (18)	0.0376 (5)
H11	0.1267	0.7824	0.7388	0.045*
C12	0.1576 (2)	0.9373 (2)	0.83021 (17)	0.0366 (5)
C13	0.2546 (2)	0.9931 (2)	0.90192 (18)	0.0380 (5)
C14	0.0264 (2)	1.0177 (2)	0.80661 (19)	0.0449 (6)
C15	−0.4115 (2)	1.0844 (2)	0.73193 (18)	0.0441 (6)
H15	−0.4890	1.0853	0.7861	0.053*
C16	−0.2848 (2)	1.0282 (2)	0.76805 (18)	0.0451 (6)
H16	−0.2770	0.9911	0.8456	0.054*
C17	−0.1706 (2)	1.0274 (2)	0.68882 (19)	0.0416 (6)
C18	−0.1806 (2)	1.0826 (2)	0.5739 (2)	0.0481 (6)
H18	−0.1022	1.0822	0.5208	0.058*
C19	−0.3081 (2)	1.1384 (3)	0.53862 (19)	0.0483 (6)
H19	−0.3147	1.1757	0.4610	0.058*
C20	−0.4266 (2)	1.1403 (2)	0.61565 (18)	0.0392 (6)
C21	−0.5644 (2)	1.1962 (2)	0.57555 (17)	0.0384 (5)
C22	−0.5909 (2)	1.2058 (2)	0.45324 (19)	0.0473 (6)
H22	−0.5202	1.1791	0.3964	0.057*
C23	−0.7190 (3)	1.2539 (3)	0.4155 (2)	0.0490 (6)
H23	−0.7338	1.2605	0.3336	0.059*
C24	−0.8261 (2)	1.2927 (2)	0.4976 (2)	0.0442 (6)
C25	−0.8024 (3)	1.2853 (3)	0.6196 (2)	0.0567 (7)
H25	−0.8733	1.3124	0.6761	0.068*
C26	−0.6725 (3)	1.2373 (3)	0.6565 (2)	0.0534 (7)
H26	−0.6573	1.2325	0.7384	0.064*
C27	−0.9608 (3)	1.3402 (2)	0.4561 (2)	0.0490 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0521 (11)	0.0481 (12)	0.0611 (10)	0.0095 (8)	−0.0207 (8)	−0.0165 (8)
O2	0.0338 (9)	0.0459 (10)	0.0452 (8)	0.0071 (7)	−0.0118 (7)	−0.0110 (7)
O3	0.0396 (10)	0.0559 (11)	0.0541 (9)	0.0177 (8)	−0.0193 (8)	−0.0138 (7)
O4	0.0577 (13)	0.0671 (14)	0.1019 (15)	0.0276 (10)	−0.0357 (11)	−0.0404 (11)
N1	0.0342 (12)	0.0484 (13)	0.0530 (11)	0.0099 (9)	−0.0095 (9)	−0.0056 (9)
N2	0.0480 (14)	0.0701 (17)	0.0754 (14)	0.0078 (12)	−0.0270 (12)	−0.0109 (12)
C1	0.068 (2)	0.0506 (18)	0.0788 (18)	0.0061 (14)	0.0090 (15)	−0.0119 (13)
C2	0.0434 (15)	0.0425 (15)	0.0594 (14)	0.0091 (12)	−0.0053 (11)	0.0016 (11)
C3	0.0398 (15)	0.0597 (18)	0.0569 (13)	0.0145 (12)	−0.0136 (11)	−0.0019 (12)
C4	0.0493 (18)	0.076 (2)	0.0709 (17)	0.0032 (15)	−0.0055 (13)	−0.0118 (14)
C5	0.0326 (13)	0.0376 (13)	0.0321 (10)	−0.0006 (10)	−0.0022 (9)	−0.0031 (8)
C6	0.0272 (13)	0.0503 (15)	0.0402 (11)	0.0010 (10)	−0.0060 (9)	−0.0051 (10)
C7	0.0288 (12)	0.0451 (15)	0.0392 (11)	0.0047 (10)	−0.0013 (9)	0.0000 (9)
C8	0.0362 (14)	0.0435 (15)	0.0537 (12)	0.0052 (11)	−0.0062 (10)	−0.0079 (10)
C9	0.0345 (14)	0.0462 (15)	0.0476 (12)	−0.0006 (11)	−0.0094 (10)	−0.0076 (10)
C10	0.0296 (13)	0.0418 (14)	0.0364 (10)	0.0004 (10)	−0.0047 (9)	−0.0019 (9)
C11	0.0309 (13)	0.0460 (15)	0.0363 (10)	−0.0018 (10)	−0.0079 (9)	−0.0019 (9)
C12	0.0319 (13)	0.0412 (14)	0.0361 (10)	0.0022 (10)	−0.0066 (9)	−0.0022 (9)
C13	0.0344 (13)	0.0426 (15)	0.0361 (10)	0.0045 (10)	−0.0054 (9)	−0.0042 (9)
C14	0.0419 (15)	0.0454 (16)	0.0473 (12)	0.0046 (12)	−0.0115 (11)	−0.0078 (11)
C15	0.0358 (14)	0.0542 (16)	0.0403 (11)	0.0034 (11)	−0.0019 (10)	0.0026 (10)
C16	0.0452 (16)	0.0518 (16)	0.0366 (11)	0.0054 (11)	−0.0093 (11)	0.0044 (10)
C17	0.0361 (14)	0.0406 (14)	0.0475 (12)	0.0081 (10)	−0.0137 (10)	−0.0053 (9)
C18	0.0355 (14)	0.0567 (17)	0.0491 (13)	0.0081 (12)	0.0002 (10)	0.0014 (11)
C19	0.0398 (15)	0.0617 (17)	0.0394 (11)	0.0094 (12)	−0.0030 (10)	0.0090 (10)
C20	0.0361 (13)	0.0407 (14)	0.0394 (11)	0.0044 (10)	−0.0050 (10)	0.0004 (9)
C21	0.0341 (13)	0.0407 (14)	0.0389 (11)	0.0039 (10)	−0.0047 (9)	0.0005 (9)
C22	0.0365 (14)	0.0634 (17)	0.0392 (11)	0.0073 (12)	−0.0019 (10)	−0.0004 (10)
C23	0.0471 (16)	0.0574 (17)	0.0420 (12)	0.0027 (12)	−0.0122 (11)	0.0013 (10)
C24	0.0322 (14)	0.0456 (15)	0.0544 (13)	0.0025 (11)	−0.0115 (11)	0.0003 (10)
C25	0.0391 (15)	0.078 (2)	0.0477 (13)	0.0180 (13)	−0.0009 (11)	−0.0029 (12)
C26	0.0428 (16)	0.0751 (19)	0.0386 (12)	0.0145 (13)	−0.0057 (11)	−0.0015 (11)
C27	0.0457 (16)	0.0495 (16)	0.0522 (13)	0.0011 (12)	−0.0120 (12)	−0.0058 (11)

Geometric parameters (Å, º) top

O1—C13	1.196 (3)	C9—C10	1.404 (3)
O2—C5	1.365 (3)	C9—H9	0.9300
O2—C13	1.393 (3)	C10—C11	1.401 (3)
O3—C14	1.370 (3)	C11—C12	1.360 (3)
O3—C17	1.400 (3)	C11—H11	0.9300
O4—C14	1.189 (3)	C12—C13	1.443 (3)
N1—C7	1.360 (3)	C12—C14	1.473 (3)
N1—C2	1.459 (3)	C15—C16	1.374 (3)
N1—C3	1.470 (3)	C15—C20	1.399 (3)
N2—C27	1.138 (3)	C15—H15	0.9300
C1—C2	1.504 (4)	C16—C17	1.367 (3)
C1—H1A	0.9600	C16—H16	0.9300
C1—H1B	0.9600	C17—C18	1.378 (3)
C1—H1C	0.9600	C18—C19	1.377 (3)
C2—H2A	0.9700	C18—H18	0.9300
C2—H2B	0.9700	C19—C20	1.384 (3)
C3—C4	1.493 (4)	C19—H19	0.9300
C3—H3A	0.9700	C20—C21	1.482 (3)
C3—H3B	0.9700	C21—C26	1.381 (3)
C4—H4A	0.9600	C21—C22	1.397 (3)
C4—H4B	0.9600	C22—C23	1.368 (3)
C4—H4C	0.9600	C22—H22	0.9300
C5—C6	1.370 (3)	C23—C24	1.377 (3)
C5—C10	1.405 (3)	C23—H23	0.9300
C6—C7	1.408 (3)	C24—C25	1.388 (3)
C6—H6	0.9300	C24—C27	1.439 (3)
C7—C8	1.424 (3)	C25—C26	1.380 (3)
C8—C9	1.358 (3)	C25—H25	0.9300
C8—H8	0.9300	C26—H26	0.9300

C5—O2—C13	123.43 (16)	C12—C11—H11	118.9
C14—O3—C17	117.47 (18)	C10—C11—H11	118.9
C7—N1—C2	121.64 (19)	C11—C12—C13	120.2 (2)
C7—N1—C3	121.2 (2)	C11—C12—C14	122.59 (19)
C2—N1—C3	117.10 (19)	C13—C12—C14	117.3 (2)
C2—C1—H1A	109.5	O1—C13—O2	114.84 (18)
C2—C1—H1B	109.5	O1—C13—C12	128.9 (2)
H1A—C1—H1B	109.5	O2—C13—C12	116.2 (2)
C2—C1—H1C	109.5	O4—C14—O3	122.0 (2)
H1A—C1—H1C	109.5	O4—C14—C12	127.6 (2)
H1B—C1—H1C	109.5	O3—C14—C12	110.4 (2)
N1—C2—C1	114.2 (2)	C16—C15—C20	121.6 (2)
N1—C2—H2A	108.7	C16—C15—H15	119.2
C1—C2—H2A	108.7	C20—C15—H15	119.2
N1—C2—H2B	108.7	C17—C16—C15	119.31 (18)
C1—C2—H2B	108.7	C17—C16—H16	120.3
H2A—C2—H2B	107.6	C15—C16—H16	120.3
N1—C3—C4	113.6 (2)	C16—C17—C18	121.0 (2)
N1—C3—H3A	108.8	C16—C17—O3	121.06 (18)
C4—C3—H3A	108.8	C18—C17—O3	117.9 (2)
N1—C3—H3B	108.8	C19—C18—C17	119.2 (2)
C4—C3—H3B	108.8	C19—C18—H18	120.4
H3A—C3—H3B	107.7	C17—C18—H18	120.4
C3—C4—H4A	109.5	C18—C19—C20	121.68 (19)
C3—C4—H4B	109.5	C18—C19—H19	119.2
H4A—C4—H4B	109.5	C20—C19—H19	119.2
C3—C4—H4C	109.5	C19—C20—C15	117.2 (2)
H4A—C4—H4C	109.5	C19—C20—C21	121.35 (18)
H4B—C4—H4C	109.5	C15—C20—C21	121.4 (2)
O2—C5—C6	116.87 (18)	C26—C21—C22	117.3 (2)
O2—C5—C10	119.93 (19)	C26—C21—C20	121.94 (18)
C6—C5—C10	123.2 (2)	C22—C21—C20	120.8 (2)
C5—C6—C7	119.85 (19)	C23—C22—C21	121.2 (2)
C5—C6—H6	120.1	C23—C22—H22	119.4
C7—C6—H6	120.1	C21—C22—H22	119.4
N1—C7—C6	121.63 (19)	C22—C23—C24	120.7 (2)
N1—C7—C8	120.9 (2)	C22—C23—H23	119.6
C6—C7—C8	117.5 (2)	C24—C23—H23	119.6
C9—C8—C7	121.2 (2)	C23—C24—C25	119.3 (2)
C9—C8—H8	119.4	C23—C24—C27	119.77 (19)
C7—C8—H8	119.4	C25—C24—C27	120.9 (2)
C8—C9—C10	122.0 (2)	C26—C25—C24	119.4 (2)
C8—C9—H9	119.0	C26—C25—H25	120.3
C10—C9—H9	119.0	C24—C25—H25	120.3
C11—C10—C9	125.81 (19)	C25—C26—C21	122.1 (2)
C11—C10—C5	117.9 (2)	C25—C26—H26	119.0
C9—C10—C5	116.2 (2)	C21—C26—H26	119.0
C12—C11—C10	122.29 (19)	N2—C27—C24	177.5 (3)

C7—N1—C2—C1	78.6 (3)	C17—O3—C14—C12	178.42 (18)
C3—N1—C2—C1	−98.1 (2)	C11—C12—C14—O4	168.8 (3)
C7—N1—C3—C4	−87.7 (3)	C13—C12—C14—O4	−11.6 (4)
C2—N1—C3—C4	88.9 (3)	C11—C12—C14—O3	−11.4 (3)
C13—O2—C5—C6	178.28 (18)	C13—C12—C14—O3	168.26 (18)
C13—O2—C5—C10	−1.8 (3)	C20—C15—C16—C17	0.4 (4)
O2—C5—C6—C7	179.15 (18)	C15—C16—C17—C18	0.3 (4)
C10—C5—C6—C7	−0.8 (3)	C15—C16—C17—O3	−176.0 (2)
C2—N1—C7—C6	−177.0 (2)	C14—O3—C17—C16	−68.9 (3)
C3—N1—C7—C6	−0.5 (3)	C14—O3—C17—C18	114.7 (2)
C2—N1—C7—C8	3.6 (3)	C16—C17—C18—C19	−0.5 (4)
C3—N1—C7—C8	−179.86 (19)	O3—C17—C18—C19	176.0 (2)
C5—C6—C7—N1	−177.34 (19)	C17—C18—C19—C20	−0.1 (4)
C5—C6—C7—C8	2.1 (3)	C18—C19—C20—C15	0.7 (4)
N1—C7—C8—C9	177.9 (2)	C18—C19—C20—C21	−177.7 (2)
C6—C7—C8—C9	−1.6 (3)	C16—C15—C20—C19	−0.9 (4)
C7—C8—C9—C10	−0.3 (3)	C16—C15—C20—C21	177.6 (2)
C8—C9—C10—C11	−179.9 (2)	C19—C20—C21—C26	−159.0 (2)
C8—C9—C10—C5	1.6 (3)	C15—C20—C21—C26	22.6 (4)
O2—C5—C10—C11	0.3 (3)	C19—C20—C21—C22	22.7 (3)
C6—C5—C10—C11	−179.71 (19)	C15—C20—C21—C22	−155.6 (2)
O2—C5—C10—C9	179.01 (18)	C26—C21—C22—C23	−0.1 (3)
C6—C5—C10—C9	−1.0 (3)	C20—C21—C22—C23	178.2 (2)
C9—C10—C11—C12	−179.0 (2)	C21—C22—C23—C24	−0.8 (4)
C5—C10—C11—C12	−0.4 (3)	C22—C23—C24—C25	1.4 (4)
C10—C11—C12—C13	1.8 (3)	C22—C23—C24—C27	−178.6 (2)
C10—C11—C12—C14	−178.57 (19)	C23—C24—C25—C26	−1.0 (4)
C5—O2—C13—O1	−175.22 (18)	C27—C24—C25—C26	179.0 (2)
C5—O2—C13—C12	3.0 (3)	C24—C25—C26—C21	0.1 (4)
C11—C12—C13—O1	175.0 (2)	C22—C21—C26—C25	0.5 (4)
C14—C12—C13—O1	−4.7 (3)	C20—C21—C26—C25	−177.8 (2)
C11—C12—C13—O2	−3.0 (3)	C23—C24—C27—N2	8 (6)
C14—C12—C13—O2	177.36 (17)	C25—C24—C27—N2	−172 (6)
C17—O3—C14—O4	−1.7 (3)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.93	2.53	3.446 (3)	170
C11—H11···N2ⁱⁱ	0.93	2.59	3.435 (3)	152
C16—H16···O1ⁱⁱⁱ	0.93	2.54	3.465 (3)	177
C1—H1B···Cg3^iv	0.96	2.82	3.626 (3)	142

Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) −x−1, −y+2, −z+1; (iii) −x, −y+2, −z+2; (iv) x+1, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₂N₂O₄
M_r	438.47
Crystal system, space group	Triclinic, P1
Temperature (K)	300
a, b, c (Å)	9.652 (3), 10.252 (4), 11.121 (4)
α, β, γ (°)	87.214 (10), 86.358 (10), 84.348 (11)
V (Å³)	1091.9 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.979, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	10667, 3783, 2495
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.173, 0.97
No. of reflections	3783
No. of parameters	301
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.37

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.93	2.53	3.446 (3)	170
C11—H11···N2ⁱⁱ	0.93	2.59	3.435 (3)	152
C16—H16···O1ⁱⁱⁱ	0.93	2.54	3.465 (3)	177
C1—H1B···Cg3^iv	0.96	2.82	3.626 (3)	142

Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) −x−1, −y+2, −z+1; (iii) −x, −y+2, −z+2; (iv) x+1, y−1, z.

Acknowledgements

The authors thank Professor T. N. Guru Row, Soild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for the data collection.

References

Bhat, M. A., Siddiqui, N. & Khan, S. A. (2006). Indian J. Pharm. Sci. 68, 120–124. CAS Google Scholar
Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chimichi, S., Boccalini, M., Cosimelli, B., Viola, G., Vedaldi, D. & Dall Acqua, F. (2002). Tetrahedron Lett. 43, 7473–7476. Web of Science CrossRef CAS 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

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Volume 69| Part 2| February 2013| Page o266

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