5-Benzoyl-2-(1H-indol-3-yl)-4-(4-methyl­phen­yl)-4,5-dihydro­furan-3-carbonitrile

Suresh, J.; Vishnupriya, R.; Gunasekaran, P.; Perumal, S.; Lakshman, P.L.N.

doi:10.1107/S1600536812011105

5-Benzoyl-2-(1H-indol-3-yl)-4-(4-methylphenyl)-4,5-dihydrofuran-3-carbonitrile

J. Suresh, R. Vishnupriya, P. Gunasekaran, S. Perumal and P. L. N. Lakshman

The furan ring in the title compound, C₂₇H₂₀N₂O₂, adopts a twisted conformation about the sp³—sp³ bond. The molecular structure is stabilized by an intramolecular C—H

O interaction which generates an S(6) ring motif. The crystal packing is stabilized by N—H

O and C—H

O interactions generating centrosymmetric R₂²(18) and C(6) chain motifs, respectively. A weak C—H

π interaction is also observed.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812011105/tk5068sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536812011105/tk5068Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536812011105/tk5068Isup3.cml Supplementary material

CCDC reference: 877271

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.045
wR factor = 0.133
Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         55

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT128_ALERT_4_G Alternate Setting of Space-group P21/c   .......      P21/n
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT371_ALERT_2_G Long   C(sp2)-C(sp1) Bond  C1     -   C2     ...       1.41 Ang.
PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C6
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            N1  -C1  -C2  -C3    106.00 14.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          2
            N1  -C1  -C2  -C5    -82.00 14.00   1.555   1.555   1.555   1.555
PLAT793_ALERT_4_G The Model has Chirality at C4      (Verify) ....          S
PLAT793_ALERT_4_G The Model has Chirality at C5      (Verify) ....          S

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Furanyl derivatives have calplain-inhibiting activity and are used in the preparation of medicaments for the treatment of inflammatory and immunological diseases, cardiovascular and cerebro-vascular diseases, disorders of the central or peripheral nervous system, cachexia, osteoporosis, muscular dystrophy, proliferative diseases, cataracts, rejection reactions following organ transplants and auto-immune and viral diseases (Auvin et al., 2005). The high medicinal value of these compounds in conjunction with our research interests prompted us to synthesize and report the X-ray structure of the title compound.

In the title compound (Fig 1), the five-membered furanyl ring adopts a twisted conformation as evident from the puckering parameters (Cremer & Pople, 1975) Q = 0.192 (2) Å and φ = 129.0 (6)°. The five-(N2/C38/C31/C32/C37) and six-membered (C32—C37) rings in the indole group are planar, with a dihedral angle of 0.74 (1)° between them. The dihedral angle between the phenyl rings (C42—C47 and C51—C56) is 15.24 (1)°.

Fig. 2 shows the partial packing of molecules in the crystal structure. The C—H···O and N—H···O intermolecular interactions generate C₁¹(6) chain and centrosymmetric R₂²(18) motifs, respectively (Bernstein et al., 1995). In addition, there is a weak C—H···π interaction, viz, C34—H34···Cg1ⁱⁱ_,Table 1.

Related literature top

For the biological importance of furan derivatives, see: Auvin & Chabrier De Lassauniere (2005). For hydrogen-bonding graph-set notation, see: Bernstein et al. (1995). For additional conformation analysis, see: Cremer & Pople (1975).

Experimental top

To a stirred mixture of 2-(1H-indole-3-carbonyl)-3-p-tolylacrylonitrile (1.0 molar eq.) and phenacylpyridinium bromide (1.0 molar eq.) in water (10 ml) was added drop wise triethylamine (0.25 molar eq.) at room temperature. The resulting clear solution, that slowly became turbid, was stirred at room temperature for 1 h. Then, the separated free flowing solid was filtered and washed with methanol (3 ml) to afford the title compound as a pale-yellow solid. The product thus obtained was recrystallized from an EtOH-EtOAc mixture (1:1 ratio v/v ml) to the give pure compound as pale-yellow crystals. Yield: 92%. M.pt: 502 K.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing 40% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The partial packing diagram of (I). The C—H···O and N—H···O interactions are shown as blue lines.

5-Benzoyl-2-(1H-indol-3-yl)-4-(4-methylphenyl)-4,5-dihydrofuran- 3-carbonitrile top

Crystal data top

C₂₇H₂₀N₂O₂	F(000) = 848
M_r = 404.45	D_x = 1.295 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2000 reflections
a = 9.8084 (4) Å	θ = 2–31°
b = 15.9553 (7) Å	µ = 0.08 mm⁻¹
c = 13.8782 (7) Å	T = 293 K
β = 107.185 (2)°	Block, pale-yellow
V = 2074.92 (16) Å³	0.19 × 0.15 × 0.12 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	4647 independent reflections
Radiation source: fine-focus sealed tube	3017 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 0 pixels mm^-1	θ_max = 27.3°, θ_min = 2.0°
ω and φ scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −20→20
T_min = 0.967, T_max = 0.974	l = −17→17
21144 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0581P)² + 0.5454P] where P = (F_o² + 2F_c²)/3
4647 reflections	(Δ/σ)_max < 0.001
284 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₇H₂₀N₂O₂	V = 2074.92 (16) Å³
M_r = 404.45	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.8084 (4) Å	µ = 0.08 mm⁻¹
b = 15.9553 (7) Å	T = 293 K
c = 13.8782 (7) Å	0.19 × 0.15 × 0.12 mm
β = 107.185 (2)°

Data collection top

Bruker Kappa APEXII diffractometer	4647 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3017 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.974	R_int = 0.038
21144 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.25 e Å⁻³
4647 reflections	Δρ_min = −0.22 e Å⁻³
284 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
H2	1.231 (2)	−0.0946 (12)	0.5116 (14)	0.044 (5)*
C1	0.7913 (2)	−0.08013 (11)	0.21842 (13)	0.0408 (4)
C2	0.78765 (18)	0.00744 (10)	0.23169 (12)	0.0331 (4)
C3	0.88408 (17)	0.05202 (10)	0.30178 (12)	0.0301 (4)
C4	0.71584 (17)	0.14707 (10)	0.22283 (12)	0.0318 (4)
H4	0.7178	0.1947	0.1787	0.038*
C5	0.68263 (18)	0.06474 (10)	0.15994 (12)	0.0314 (4)
H5	0.5848	0.0465	0.1531	0.038*
C6	0.7683 (3)	0.09390 (17)	−0.23642 (17)	0.0734 (7)
H6A	0.8681	0.0883	−0.2296	0.110*
H6B	0.7350	0.1474	−0.2658	0.110*
H6C	0.7163	0.0501	−0.2791	0.110*
C31	1.01403 (17)	0.02910 (10)	0.37695 (12)	0.0310 (4)
C32	1.12543 (17)	0.08399 (11)	0.43391 (12)	0.0325 (4)
C33	1.14643 (19)	0.17039 (11)	0.44071 (14)	0.0405 (4)
H33	1.0781	0.2066	0.4014	0.049*
C34	1.2696 (2)	0.20113 (13)	0.50646 (16)	0.0535 (5)
H34	1.2841	0.2588	0.5116	0.064*
C35	1.3735 (2)	0.14808 (14)	0.56565 (17)	0.0615 (6)
H35	1.4558	0.1709	0.6097	0.074*
C36	1.3567 (2)	0.06253 (14)	0.56019 (15)	0.0527 (5)
H36	1.4263	0.0268	0.5991	0.063*
C37	1.23189 (18)	0.03164 (11)	0.49441 (13)	0.0367 (4)
C38	1.05756 (18)	−0.05100 (11)	0.40606 (13)	0.0357 (4)
H38	1.0052	−0.0992	0.3819	0.043*
C41	0.60327 (18)	0.16108 (10)	0.27659 (13)	0.0337 (4)
C42	0.45710 (18)	0.18082 (11)	0.21168 (13)	0.0372 (4)
C43	0.4312 (2)	0.21107 (12)	0.11489 (14)	0.0463 (5)
H43	0.5073	0.2244	0.0906	0.056*
C44	0.2925 (2)	0.22178 (14)	0.05363 (17)	0.0619 (6)
H44	0.2753	0.2419	−0.0118	0.074*
C45	0.1806 (3)	0.20254 (16)	0.0902 (2)	0.0759 (8)
H45	0.0873	0.2089	0.0490	0.091*
C46	0.2051 (3)	0.17414 (18)	0.1867 (2)	0.0786 (8)
H46	0.1287	0.1622	0.2112	0.094*
C47	0.3427 (2)	0.16313 (14)	0.24769 (17)	0.0574 (6)
H47	0.3589	0.1437	0.3133	0.069*
C51	0.70509 (18)	0.07130 (10)	0.05677 (12)	0.0320 (4)
C52	0.59093 (19)	0.08565 (11)	−0.02828 (13)	0.0380 (4)
H52	0.4993	0.0900	−0.0222	0.046*
C53	0.6116 (2)	0.09362 (12)	−0.12209 (14)	0.0447 (5)
H53	0.5334	0.1032	−0.1782	0.054*
C54	0.7455 (2)	0.08765 (12)	−0.13439 (15)	0.0465 (5)
C55	0.8592 (2)	0.07429 (13)	−0.04929 (16)	0.0503 (5)
H55	0.9509	0.0707	−0.0555	0.060*
C56	0.8396 (2)	0.06610 (12)	0.04483 (14)	0.0426 (4)
H56	0.9181	0.0570	0.1009	0.051*
N1	0.7928 (2)	−0.15113 (11)	0.20826 (15)	0.0670 (6)
N2	1.18746 (16)	−0.04969 (10)	0.47495 (11)	0.0387 (4)
O1	0.85398 (12)	0.13585 (7)	0.29520 (9)	0.0369 (3)
O2	0.62895 (14)	0.14959 (8)	0.36623 (9)	0.0452 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0479 (11)	0.0332 (10)	0.0347 (10)	0.0026 (8)	0.0019 (8)	−0.0008 (8)
C2	0.0382 (9)	0.0284 (8)	0.0297 (9)	0.0029 (7)	0.0054 (7)	0.0004 (7)
C3	0.0333 (9)	0.0274 (8)	0.0293 (9)	0.0050 (7)	0.0086 (7)	0.0024 (7)
C4	0.0329 (9)	0.0289 (9)	0.0287 (9)	0.0038 (6)	0.0014 (7)	0.0007 (7)
C5	0.0322 (9)	0.0284 (8)	0.0306 (9)	0.0002 (6)	0.0047 (7)	−0.0014 (7)
C6	0.0889 (19)	0.0920 (19)	0.0465 (14)	0.0128 (14)	0.0310 (13)	0.0068 (12)
C31	0.0336 (9)	0.0323 (9)	0.0273 (9)	0.0033 (7)	0.0093 (7)	0.0010 (7)
C32	0.0326 (9)	0.0384 (9)	0.0272 (9)	0.0009 (7)	0.0099 (7)	0.0021 (7)
C33	0.0412 (10)	0.0380 (10)	0.0403 (11)	−0.0008 (8)	0.0091 (8)	0.0031 (8)
C34	0.0522 (13)	0.0450 (12)	0.0566 (13)	−0.0126 (9)	0.0057 (10)	−0.0017 (10)
C35	0.0471 (13)	0.0626 (15)	0.0604 (15)	−0.0160 (10)	−0.0061 (11)	0.0037 (11)
C36	0.0389 (11)	0.0599 (13)	0.0495 (12)	−0.0012 (9)	−0.0021 (9)	0.0106 (10)
C37	0.0345 (10)	0.0417 (10)	0.0328 (9)	0.0018 (7)	0.0083 (8)	0.0054 (7)
C38	0.0385 (10)	0.0363 (9)	0.0306 (9)	0.0027 (7)	0.0075 (8)	0.0002 (7)
C41	0.0402 (10)	0.0257 (8)	0.0306 (9)	0.0035 (7)	0.0031 (7)	−0.0009 (7)
C42	0.0365 (10)	0.0361 (9)	0.0343 (10)	0.0075 (7)	0.0030 (8)	−0.0048 (7)
C43	0.0479 (11)	0.0472 (11)	0.0369 (11)	0.0155 (9)	0.0020 (9)	−0.0002 (8)
C44	0.0636 (15)	0.0593 (14)	0.0459 (13)	0.0249 (11)	−0.0098 (11)	−0.0050 (10)
C45	0.0428 (13)	0.0837 (18)	0.081 (2)	0.0188 (12)	−0.0127 (13)	−0.0223 (15)
C46	0.0410 (13)	0.105 (2)	0.085 (2)	0.0046 (13)	0.0114 (13)	−0.0088 (16)
C47	0.0429 (12)	0.0740 (15)	0.0535 (13)	0.0057 (10)	0.0115 (10)	0.0012 (11)
C51	0.0358 (9)	0.0263 (8)	0.0310 (9)	0.0028 (7)	0.0052 (7)	−0.0013 (7)
C52	0.0342 (10)	0.0407 (10)	0.0360 (10)	−0.0023 (7)	0.0054 (8)	−0.0015 (8)
C53	0.0501 (12)	0.0482 (11)	0.0300 (10)	−0.0001 (9)	0.0029 (9)	0.0024 (8)
C54	0.0597 (13)	0.0430 (11)	0.0390 (11)	0.0073 (9)	0.0180 (10)	0.0016 (8)
C55	0.0473 (12)	0.0582 (13)	0.0499 (12)	0.0167 (9)	0.0210 (10)	0.0063 (10)
C56	0.0373 (10)	0.0482 (11)	0.0391 (11)	0.0107 (8)	0.0062 (8)	0.0030 (8)
N1	0.0830 (14)	0.0337 (10)	0.0688 (13)	0.0048 (9)	−0.0014 (11)	−0.0071 (8)
N2	0.0395 (8)	0.0369 (8)	0.0357 (8)	0.0085 (7)	0.0051 (7)	0.0084 (7)
O1	0.0331 (6)	0.0279 (6)	0.0415 (7)	0.0036 (5)	−0.0016 (5)	−0.0029 (5)
O2	0.0515 (8)	0.0508 (8)	0.0290 (7)	0.0095 (6)	0.0051 (6)	0.0042 (6)

Geometric parameters (Å, º) top

C1—N1	1.142 (2)	C37—N2	1.370 (2)
C1—C2	1.411 (2)	C38—N2	1.348 (2)
C2—C3	1.343 (2)	C38—H38	0.9300
C2—C5	1.511 (2)	C41—O2	1.208 (2)
C3—O1	1.3670 (18)	C41—C42	1.484 (2)
C3—C31	1.436 (2)	C42—C43	1.379 (3)
C4—O1	1.4397 (19)	C42—C47	1.386 (3)
C4—C41	1.521 (2)	C43—C44	1.385 (3)
C4—C5	1.557 (2)	C43—H43	0.9300
C4—H4	0.9800	C44—C45	1.374 (3)
C5—C51	1.515 (2)	C44—H44	0.9300
C5—H5	0.9800	C45—C46	1.366 (4)
C6—C54	1.501 (3)	C45—H45	0.9300
C6—H6A	0.9600	C46—C47	1.376 (3)
C6—H6B	0.9600	C46—H46	0.9300
C6—H6C	0.9600	C47—H47	0.9300
C31—C38	1.370 (2)	C51—C56	1.380 (2)
C31—C32	1.441 (2)	C51—C52	1.385 (2)
C32—C33	1.393 (2)	C52—C53	1.381 (3)
C32—C37	1.405 (2)	C52—H52	0.9300
C33—C34	1.372 (3)	C53—C54	1.377 (3)
C33—H33	0.9300	C53—H53	0.9300
C34—C35	1.391 (3)	C54—C55	1.381 (3)
C34—H34	0.9300	C55—C56	1.381 (3)
C35—C36	1.374 (3)	C55—H55	0.9300
C35—H35	0.9300	C56—H56	0.9300
C36—C37	1.383 (3)	N2—H2	0.91 (2)
C36—H36	0.9300

N1—C1—C2	179.0 (2)	N2—C38—C31	109.98 (15)
C3—C2—C1	125.41 (15)	N2—C38—H38	125.0
C3—C2—C5	110.74 (14)	C31—C38—H38	125.0
C1—C2—C5	123.49 (15)	O2—C41—C42	121.82 (17)
C2—C3—O1	112.21 (14)	O2—C41—C4	121.48 (15)
C2—C3—C31	132.51 (15)	C42—C41—C4	116.40 (14)
O1—C3—C31	115.18 (14)	C43—C42—C47	119.15 (18)
O1—C4—C41	110.25 (13)	C43—C42—C41	122.17 (17)
O1—C4—C5	106.50 (12)	C47—C42—C41	118.55 (17)
C41—C4—C5	109.70 (13)	C42—C43—C44	120.4 (2)
O1—C4—H4	110.1	C42—C43—H43	119.8
C41—C4—H4	110.1	C44—C43—H43	119.8
C5—C4—H4	110.1	C45—C44—C43	119.5 (2)
C2—C5—C51	113.80 (13)	C45—C44—H44	120.2
C2—C5—C4	98.75 (12)	C43—C44—H44	120.2
C51—C5—C4	113.99 (13)	C46—C45—C44	120.5 (2)
C2—C5—H5	109.9	C46—C45—H45	119.7
C51—C5—H5	109.9	C44—C45—H45	119.7
C4—C5—H5	109.9	C45—C46—C47	120.2 (2)
C54—C6—H6A	109.5	C45—C46—H46	119.9
C54—C6—H6B	109.5	C47—C46—H46	119.9
H6A—C6—H6B	109.5	C46—C47—C42	120.2 (2)
C54—C6—H6C	109.5	C46—C47—H47	119.9
H6A—C6—H6C	109.5	C42—C47—H47	119.9
H6B—C6—H6C	109.5	C56—C51—C52	117.94 (16)
C38—C31—C3	125.75 (15)	C56—C51—C5	121.36 (15)
C38—C31—C32	106.58 (15)	C52—C51—C5	120.67 (15)
C3—C31—C32	127.64 (15)	C53—C52—C51	120.77 (17)
C33—C32—C37	118.61 (16)	C53—C52—H52	119.6
C33—C32—C31	135.37 (16)	C51—C52—H52	119.6
C37—C32—C31	106.01 (15)	C54—C53—C52	121.43 (18)
C34—C33—C32	118.84 (17)	C54—C53—H53	119.3
C34—C33—H33	120.6	C52—C53—H53	119.3
C32—C33—H33	120.6	C53—C54—C55	117.63 (18)
C33—C34—C35	121.53 (19)	C53—C54—C6	121.72 (19)
C33—C34—H34	119.2	C55—C54—C6	120.64 (19)
C35—C34—H34	119.2	C54—C55—C56	121.37 (19)
C36—C35—C34	121.10 (19)	C54—C55—H55	119.3
C36—C35—H35	119.4	C56—C55—H55	119.3
C34—C35—H35	119.4	C51—C56—C55	120.85 (17)
C35—C36—C37	117.31 (18)	C51—C56—H56	119.6
C35—C36—H36	121.3	C55—C56—H56	119.6
C37—C36—H36	121.3	C38—N2—C37	109.46 (14)
N2—C37—C36	129.44 (17)	C38—N2—H2	125.2 (12)
N2—C37—C32	107.95 (15)	C37—N2—H2	124.4 (12)
C36—C37—C32	122.60 (17)	C3—O1—C4	107.96 (12)

N1—C1—C2—C3	106 (14)	C5—C4—C41—O2	105.78 (18)
N1—C1—C2—C5	−82 (14)	O1—C4—C41—C42	175.00 (13)
C1—C2—C3—O1	178.88 (16)	C5—C4—C41—C42	−68.02 (17)
C5—C2—C3—O1	5.6 (2)	O2—C41—C42—C43	166.10 (17)
C1—C2—C3—C31	2.8 (3)	C4—C41—C42—C43	−20.1 (2)
C5—C2—C3—C31	−170.48 (17)	O2—C41—C42—C47	−18.1 (3)
C3—C2—C5—C51	106.09 (16)	C4—C41—C42—C47	155.73 (17)
C1—C2—C5—C51	−67.3 (2)	C47—C42—C43—C44	−1.5 (3)
C3—C2—C5—C4	−15.07 (18)	C41—C42—C43—C44	174.33 (17)
C1—C2—C5—C4	171.50 (16)	C42—C43—C44—C45	0.4 (3)
O1—C4—C5—C2	18.97 (16)	C43—C44—C45—C46	0.9 (4)
C41—C4—C5—C2	−100.33 (14)	C44—C45—C46—C47	−1.1 (4)
O1—C4—C5—C51	−102.04 (15)	C45—C46—C47—C42	0.0 (4)
C41—C4—C5—C51	138.65 (14)	C43—C42—C47—C46	1.3 (3)
C2—C3—C31—C38	−12.6 (3)	C41—C42—C47—C46	−174.7 (2)
O1—C3—C31—C38	171.41 (15)	C2—C5—C51—C56	−32.8 (2)
C2—C3—C31—C32	165.29 (18)	C4—C5—C51—C56	79.46 (19)
O1—C3—C31—C32	−10.7 (2)	C2—C5—C51—C52	149.49 (15)
C38—C31—C32—C33	−179.13 (19)	C4—C5—C51—C52	−98.29 (18)
C3—C31—C32—C33	2.7 (3)	C56—C51—C52—C53	0.6 (3)
C38—C31—C32—C37	0.53 (18)	C5—C51—C52—C53	178.47 (16)
C3—C31—C32—C37	−177.68 (16)	C51—C52—C53—C54	0.0 (3)
C37—C32—C33—C34	−0.3 (3)	C52—C53—C54—C55	−0.7 (3)
C31—C32—C33—C34	179.29 (19)	C52—C53—C54—C6	178.30 (19)
C32—C33—C34—C35	0.3 (3)	C53—C54—C55—C56	0.8 (3)
C33—C34—C35—C36	0.2 (4)	C6—C54—C55—C56	−178.2 (2)
C34—C35—C36—C37	−0.7 (3)	C52—C51—C56—C55	−0.5 (3)
C35—C36—C37—N2	−179.33 (19)	C5—C51—C56—C55	−178.35 (16)
C35—C36—C37—C32	0.6 (3)	C54—C55—C56—C51	−0.2 (3)
C33—C32—C37—N2	179.83 (15)	C31—C38—N2—C37	1.1 (2)
C31—C32—C37—N2	0.10 (19)	C36—C37—N2—C38	179.26 (19)
C33—C32—C37—C36	−0.1 (3)	C32—C37—N2—C38	−0.7 (2)
C31—C32—C37—C36	−179.88 (17)	C2—C3—O1—C4	7.86 (18)
C3—C31—C38—N2	177.26 (15)	C31—C3—O1—C4	−175.33 (14)
C32—C31—C38—N2	−0.99 (19)	C41—C4—O1—C3	101.52 (14)
O1—C4—C41—O2	−11.2 (2)	C5—C4—O1—C3	−17.43 (17)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C51–C56 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C33—H33···O1	0.93	2.52	3.032 (2)	115
N2—H2···O2ⁱ	0.91 (2)	2.04 (2)	2.880 (2)	154
C44—H44···O2ⁱⁱ	0.93	2.55	3.329 (3)	142
C34—H34···Cg1ⁱⁱⁱ	0.93	2.69	3.556 (3)	156

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

Experimental details

Crystal data
Chemical formula	C₂₇H₂₀N₂O₂
M_r	404.45
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.8084 (4), 15.9553 (7), 13.8782 (7)
β (°)	107.185 (2)
V (Å³)	2074.92 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.19 × 0.15 × 0.12

Data collection
Diffractometer	Bruker Kappa APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.967, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	21144, 4647, 3017
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.646

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.133, 1.02
No. of reflections	4647
No. of parameters	284
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.22

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).