(±)-trans-5-Benzoyl-2-(1H-indol-3-yl)-4-phenyl-4,5-dihydro­furan-3-carbonitrile

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

doi:10.1107/S1600536812018430

(±)-trans-5-Benzoyl-2-(1H-indol-3-yl)-4-phenyl-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, C₂₆H₁₈N₂O₂, is twisted about the C(H)—C(H) bond. The molecular structure is stabilized by an intramolecular C—H⋯O interaction, which generates an S(6) ring motif. The presence of N—H⋯N hydrogen bonds leads to inversion dimers, which are stabilized in the crystal packing by C—H⋯O and C—H⋯π interactions, forming layers that stack along the a axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812018430/tk5086sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536812018430/tk5086Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536812018430/tk5086Isup3.cml Supplementary material

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.042
wR factor = 0.117
Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600          7

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT007_ALERT_5_G Note: Number of Unrefined D-H Atoms ............          1
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            N2  -C1  -C2  -C3     91.00 13.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          2
            N2  -C1  -C2  -C5    -90.00 13.00   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
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

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

Comment top

Benzofurans have physiological, pharmacological and toxic properties, and there is continuing interest in their synthesis (Kappe et al., 1997). Various benzofuran derivatives have been investigated as estrogen receptor ligands, because selective estrogen receptor modulators such as ralixofene have emerged as potential therapeutics for the prevention and treatment of osteoporosis (Sato et al., 1999; Smith et al., 2002). In view of their high medicinal value, and in conjunction with our research interests, we were prompted to synthesize and report the X-ray structure determination of the title compound, (I).

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 = 0.1429 (2) Å and φ = 126.0 (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 0.95 (1)° between them. The dihedral angle between the phenyl rings (C42—C47 and C51—C56) is 31.56 (1)°. The molecular structure is stabilized by an intramolecular C—H···O interaction which generates an S(6) ring motif (Bernstein et al., 1995).

The presence of N—H···N hydrogen bonds leads to inversion dimers which are stabilised in the crystal packing by C—H···O and C—H···π interactions, Table 1, to form layers that stack along the a axis, Fig. 2.

Related literature top

For graph-set notation, see: Bernstein et al. (1995). For the importance of furan derivatives, see: Kappe et al. (1997); Sato et al. (1999); Smith et al. (2002). For additional conformation analysis, see: Cremer & Pople (1975).

Experimental top

To a stirred mixture of 2-(1H-indole-3-carbonyl)-3-phenylacrylonitrile (1.0 eq.) and phenacylpyridinium bromide (1.0 eq.) in water (10 ml) was added drop-wise triethylamine (0.25 eq.) at room temperature. The resulting clear solution, that slowly became turbid, was stirred at room temperature for 0.5 h. Then the separated free-flowing solid was filtered and washed with methanol (3 ml) to afford the title compound as pale-yellow solids. The product was recrystallized from EtOH/EtOAc mixture (1:1 ratio v/v ml) to give pure compound, as pale-yellow crystals. M. pt: 521 K; Yield: 88%.

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 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The packing diagram of the molecule (I). The C—H···O interactions are shown as dashed lines.

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

Crystal data top

C₂₆H₁₈N₂O₂	F(000) = 816
M_r = 390.42	D_x = 1.327 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2000 reflections
a = 12.4027 (5) Å	θ = 2–31°
b = 8.3722 (4) Å	µ = 0.09 mm⁻¹
c = 19.7472 (8) Å	T = 293 K
β = 107.570 (2)°	Block, pale-yellow
V = 1954.85 (15) Å³	0.17 × 0.14 × 0.13 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	4403 independent reflections
Radiation source: fine-focus sealed tube	3021 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 0 pixels mm^-1	θ_max = 27.3°, θ_min = 2.2°
ω and φ scans	h = −12→16
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→10
T_min = 0.967, T_max = 0.974	l = −25→25
20260 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0537P)² + 0.2502P] where P = (F_o² + 2F_c²)/3
4403 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₂₆H₁₈N₂O₂	V = 1954.85 (15) Å³
M_r = 390.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.4027 (5) Å	µ = 0.09 mm⁻¹
b = 8.3722 (4) Å	T = 293 K
c = 19.7472 (8) Å	0.17 × 0.14 × 0.13 mm
β = 107.570 (2)°

Data collection top

Bruker Kappa APEXII diffractometer	4403 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3021 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.974	R_int = 0.030
20260 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.02	Δρ_max = 0.16 e Å⁻³
4403 reflections	Δρ_min = −0.15 e Å⁻³
271 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
C1	0.67286 (12)	0.45451 (19)	0.17299 (7)	0.0470 (3)
C2	0.63051 (11)	0.34109 (17)	0.21081 (7)	0.0444 (3)
C3	0.52658 (12)	0.27563 (17)	0.18813 (7)	0.0450 (3)
C4	0.59768 (11)	0.18757 (18)	0.30149 (7)	0.0460 (3)
H4	0.6215	0.0796	0.3187	0.055*
C5	0.69611 (11)	0.27397 (18)	0.28285 (7)	0.0446 (3)
H5	0.7251	0.3614	0.3164	0.054*
C31	0.43701 (12)	0.28633 (17)	0.12162 (7)	0.0463 (3)
C32	0.32001 (12)	0.24303 (17)	0.10900 (8)	0.0484 (4)
C33	0.25537 (13)	0.1932 (2)	0.15212 (9)	0.0598 (4)
H33	0.2878	0.1823	0.2009	0.072*
C34	0.14258 (15)	0.1608 (2)	0.12050 (11)	0.0744 (5)
H34	0.0985	0.1280	0.1486	0.089*
C35	0.09299 (16)	0.1758 (3)	0.04764 (12)	0.0834 (6)
H35	0.0169	0.1508	0.0279	0.100*
C36	0.15389 (16)	0.2265 (2)	0.00444 (10)	0.0766 (6)
H36	0.1205	0.2373	−0.0443	0.092*
C37	0.26741 (13)	0.26136 (19)	0.03599 (8)	0.0569 (4)
C38	0.44868 (14)	0.32868 (19)	0.05720 (8)	0.0549 (4)
H38	0.5155	0.3629	0.0496	0.066*
C41	0.56106 (12)	0.27837 (19)	0.35731 (8)	0.0491 (4)
C42	0.64154 (12)	0.28240 (18)	0.43077 (7)	0.0464 (3)
C43	0.62343 (14)	0.3942 (2)	0.47757 (8)	0.0593 (4)
H43	0.5625	0.4641	0.4627	0.071*
C44	0.69484 (17)	0.4028 (2)	0.54600 (9)	0.0731 (5)
H44	0.6822	0.4786	0.5772	0.088*
C45	0.78458 (17)	0.3001 (2)	0.56826 (9)	0.0728 (5)
H45	0.8327	0.3062	0.6146	0.087*
C46	0.80372 (15)	0.1881 (2)	0.52240 (9)	0.0679 (5)
H46	0.8645	0.1182	0.5377	0.081*
C47	0.73263 (13)	0.1793 (2)	0.45343 (8)	0.0567 (4)
H47	0.7460	0.1040	0.4223	0.068*
C51	0.79172 (11)	0.16457 (18)	0.28071 (7)	0.0448 (3)
C52	0.90157 (12)	0.1926 (2)	0.32275 (8)	0.0612 (4)
H52	0.9172	0.2801	0.3532	0.073*
C53	0.98818 (14)	0.0916 (3)	0.31985 (10)	0.0726 (5)
H53	1.0616	0.1117	0.3484	0.087*
C54	0.96707 (15)	−0.0370 (2)	0.27562 (9)	0.0685 (5)
H54	1.0259	−0.1034	0.2732	0.082*
C55	0.85815 (15)	−0.0680 (2)	0.23456 (9)	0.0661 (5)
H55	0.8430	−0.1567	0.2049	0.079*
C56	0.77161 (13)	0.0315 (2)	0.23725 (8)	0.0556 (4)
H56	0.6982	0.0090	0.2094	0.067*
N1	0.34776 (12)	0.31303 (17)	0.00616 (6)	0.0629 (4)
H1	0.3359	0.3326	−0.0382	0.076*
N2	0.70692 (12)	0.54844 (18)	0.14254 (7)	0.0630 (4)
O1	0.50438 (8)	0.17832 (12)	0.23712 (5)	0.0523 (3)
O2	0.47216 (10)	0.34802 (17)	0.34197 (6)	0.0765 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0484 (8)	0.0492 (9)	0.0412 (7)	0.0003 (6)	0.0104 (6)	0.0016 (7)
C2	0.0464 (7)	0.0463 (8)	0.0394 (7)	0.0010 (6)	0.0112 (6)	0.0031 (6)
C3	0.0495 (8)	0.0443 (8)	0.0401 (7)	0.0024 (6)	0.0120 (6)	0.0019 (6)
C4	0.0439 (7)	0.0510 (9)	0.0386 (7)	−0.0013 (6)	0.0056 (6)	0.0071 (6)
C5	0.0459 (7)	0.0485 (8)	0.0365 (7)	−0.0046 (6)	0.0081 (6)	0.0004 (6)
C31	0.0492 (8)	0.0453 (8)	0.0407 (7)	0.0048 (6)	0.0077 (6)	−0.0002 (6)
C32	0.0478 (8)	0.0429 (8)	0.0480 (8)	0.0054 (6)	0.0048 (6)	−0.0030 (6)
C33	0.0540 (9)	0.0594 (11)	0.0638 (10)	0.0033 (7)	0.0146 (8)	−0.0020 (8)
C34	0.0556 (10)	0.0716 (12)	0.0970 (14)	−0.0004 (9)	0.0246 (10)	−0.0079 (11)
C35	0.0495 (10)	0.0815 (14)	0.1046 (16)	0.0016 (9)	0.0012 (11)	−0.0131 (12)
C36	0.0620 (11)	0.0755 (13)	0.0698 (12)	0.0075 (9)	−0.0140 (9)	−0.0043 (10)
C37	0.0569 (9)	0.0504 (9)	0.0531 (9)	0.0066 (7)	0.0009 (7)	−0.0010 (7)
C38	0.0605 (9)	0.0560 (10)	0.0432 (8)	−0.0007 (7)	0.0081 (7)	0.0017 (7)
C41	0.0444 (8)	0.0544 (9)	0.0477 (8)	0.0006 (7)	0.0128 (6)	0.0101 (7)
C42	0.0485 (8)	0.0507 (9)	0.0414 (7)	−0.0031 (6)	0.0157 (6)	0.0091 (6)
C43	0.0688 (10)	0.0625 (10)	0.0503 (9)	0.0030 (8)	0.0235 (8)	0.0045 (8)
C44	0.0986 (14)	0.0742 (13)	0.0470 (9)	−0.0058 (11)	0.0226 (9)	−0.0028 (9)
C45	0.0854 (13)	0.0796 (13)	0.0441 (9)	−0.0160 (10)	0.0055 (8)	0.0071 (9)
C46	0.0655 (10)	0.0733 (12)	0.0560 (10)	0.0025 (9)	0.0050 (8)	0.0166 (9)
C47	0.0604 (9)	0.0595 (10)	0.0472 (8)	0.0034 (7)	0.0118 (7)	0.0077 (7)
C51	0.0427 (7)	0.0535 (9)	0.0351 (7)	−0.0030 (6)	0.0071 (5)	0.0062 (6)
C52	0.0477 (8)	0.0690 (11)	0.0578 (9)	−0.0054 (8)	0.0020 (7)	−0.0060 (8)
C53	0.0426 (8)	0.0892 (14)	0.0756 (11)	0.0024 (9)	0.0022 (8)	0.0033 (11)
C54	0.0583 (10)	0.0767 (13)	0.0704 (11)	0.0155 (9)	0.0194 (8)	0.0117 (10)
C55	0.0697 (11)	0.0649 (11)	0.0615 (10)	0.0089 (9)	0.0167 (8)	−0.0048 (8)
C56	0.0491 (8)	0.0642 (10)	0.0470 (8)	−0.0022 (7)	0.0049 (6)	−0.0029 (8)
N1	0.0715 (9)	0.0669 (9)	0.0396 (7)	0.0017 (7)	0.0006 (6)	0.0059 (6)
N2	0.0694 (9)	0.0656 (9)	0.0540 (8)	−0.0076 (7)	0.0185 (7)	0.0088 (7)
O1	0.0495 (6)	0.0612 (7)	0.0406 (5)	−0.0114 (5)	0.0055 (4)	0.0070 (5)
O2	0.0551 (7)	0.1000 (10)	0.0680 (7)	0.0243 (7)	0.0089 (6)	−0.0007 (7)

Geometric parameters (Å, º) top

C1—N2	1.1454 (18)	C38—H38	0.9300
C1—C2	1.404 (2)	C41—O2	1.2024 (17)
C2—C3	1.3469 (19)	C41—C42	1.4925 (19)
C2—C5	1.5174 (18)	C42—C43	1.380 (2)
C3—O1	1.3552 (17)	C42—C47	1.385 (2)
C3—C31	1.4443 (19)	C43—C44	1.376 (2)
C4—O1	1.4398 (15)	C43—H43	0.9300
C4—C41	1.517 (2)	C44—C45	1.370 (3)
C4—C5	1.5558 (19)	C44—H44	0.9300
C4—H4	0.9800	C45—C46	1.373 (3)
C5—C51	1.509 (2)	C45—H45	0.9300
C5—H5	0.9800	C46—C47	1.383 (2)
C31—C38	1.370 (2)	C46—H46	0.9300
C31—C32	1.442 (2)	C47—H47	0.9300
C32—C33	1.398 (2)	C51—C56	1.382 (2)
C32—C37	1.400 (2)	C51—C52	1.3847 (19)
C33—C34	1.376 (2)	C52—C53	1.381 (2)
C33—H33	0.9300	C52—H52	0.9300
C34—C35	1.389 (3)	C53—C54	1.361 (3)
C34—H34	0.9300	C53—H53	0.9300
C35—C36	1.367 (3)	C54—C55	1.374 (2)
C35—H35	0.9300	C54—H54	0.9300
C36—C37	1.388 (2)	C55—C56	1.372 (2)
C36—H36	0.9300	C55—H55	0.9300
C37—N1	1.372 (2)	C56—H56	0.9300
C38—N1	1.3557 (19)	N1—H1	0.8600

N2—C1—C2	179.19 (17)	O2—C41—C42	121.82 (14)
C3—C2—C1	124.91 (13)	O2—C41—C4	120.85 (13)
C3—C2—C5	110.46 (12)	C42—C41—C4	117.29 (12)
C1—C2—C5	124.63 (12)	C43—C42—C47	119.23 (14)
C2—C3—O1	112.80 (12)	C43—C42—C41	118.02 (13)
C2—C3—C31	132.33 (14)	C47—C42—C41	122.75 (14)
O1—C3—C31	114.84 (12)	C44—C43—C42	120.44 (16)
O1—C4—C41	109.35 (11)	C44—C43—H43	119.8
O1—C4—C5	107.16 (10)	C42—C43—H43	119.8
C41—C4—C5	111.55 (12)	C45—C44—C43	120.12 (17)
O1—C4—H4	109.6	C45—C44—H44	119.9
C41—C4—H4	109.6	C43—C44—H44	119.9
C5—C4—H4	109.6	C44—C45—C46	120.17 (16)
C51—C5—C2	113.71 (11)	C44—C45—H45	119.9
C51—C5—C4	113.81 (12)	C46—C45—H45	119.9
C2—C5—C4	99.04 (10)	C45—C46—C47	120.03 (17)
C51—C5—H5	109.9	C45—C46—H46	120.0
C2—C5—H5	109.9	C47—C46—H46	120.0
C4—C5—H5	109.9	C46—C47—C42	120.01 (16)
C38—C31—C32	106.70 (12)	C46—C47—H47	120.0
C38—C31—C3	126.34 (14)	C42—C47—H47	120.0
C32—C31—C3	126.81 (13)	C56—C51—C52	117.97 (14)
C33—C32—C37	119.04 (14)	C56—C51—C5	120.70 (12)
C33—C32—C31	134.57 (13)	C52—C51—C5	121.32 (14)
C37—C32—C31	106.39 (14)	C53—C52—C51	120.55 (16)
C34—C33—C32	118.29 (16)	C53—C52—H52	119.7
C34—C33—H33	120.9	C51—C52—H52	119.7
C32—C33—H33	120.9	C54—C53—C52	120.60 (15)
C33—C34—C35	121.58 (19)	C54—C53—H53	119.7
C33—C34—H34	119.2	C52—C53—H53	119.7
C35—C34—H34	119.2	C53—C54—C55	119.50 (16)
C36—C35—C34	121.28 (17)	C53—C54—H54	120.3
C36—C35—H35	119.4	C55—C54—H54	120.3
C34—C35—H35	119.4	C56—C55—C54	120.24 (17)
C35—C36—C37	117.53 (17)	C56—C55—H55	119.9
C35—C36—H36	121.2	C54—C55—H55	119.9
C37—C36—H36	121.2	C55—C56—C51	121.11 (14)
N1—C37—C36	130.07 (16)	C55—C56—H56	119.4
N1—C37—C32	107.68 (13)	C51—C56—H56	119.4
C36—C37—C32	122.24 (17)	C38—N1—C37	109.80 (13)
N1—C38—C31	109.43 (15)	C38—N1—H1	125.1
N1—C38—H38	125.3	C37—N1—H1	125.1
C31—C38—H38	125.3	C3—O1—C4	108.40 (10)

N2—C1—C2—C3	91 (13)	O1—C4—C41—O2	−10.0 (2)
N2—C1—C2—C5	−90 (13)	C5—C4—C41—O2	108.38 (16)
C1—C2—C3—O1	−175.50 (13)	O1—C4—C41—C42	172.28 (11)
C5—C2—C3—O1	5.01 (17)	C5—C4—C41—C42	−69.37 (16)
C1—C2—C3—C31	6.4 (3)	O2—C41—C42—C43	−13.3 (2)
C5—C2—C3—C31	−173.05 (15)	C4—C41—C42—C43	164.41 (13)
C3—C2—C5—C51	109.37 (14)	O2—C41—C42—C47	166.66 (16)
C1—C2—C5—C51	−70.13 (18)	C4—C41—C42—C47	−15.6 (2)
C3—C2—C5—C4	−11.72 (15)	C47—C42—C43—C44	−0.2 (2)
C1—C2—C5—C4	168.78 (14)	C41—C42—C43—C44	179.82 (15)
O1—C4—C5—C51	−106.79 (12)	C42—C43—C44—C45	−0.1 (3)
C41—C4—C5—C51	133.55 (12)	C43—C44—C45—C46	0.1 (3)
O1—C4—C5—C2	14.22 (14)	C44—C45—C46—C47	0.3 (3)
C41—C4—C5—C2	−105.43 (12)	C45—C46—C47—C42	−0.6 (3)
C2—C3—C31—C38	21.4 (3)	C43—C42—C47—C46	0.5 (2)
O1—C3—C31—C38	−156.61 (14)	C41—C42—C47—C46	−179.48 (14)
C2—C3—C31—C32	−163.71 (16)	C2—C5—C51—C56	−56.54 (18)
O1—C3—C31—C32	18.3 (2)	C4—C5—C51—C56	55.88 (17)
C38—C31—C32—C33	−178.57 (17)	C2—C5—C51—C52	124.44 (15)
C3—C31—C32—C33	5.7 (3)	C4—C5—C51—C52	−123.14 (15)
C38—C31—C32—C37	0.40 (16)	C56—C51—C52—C53	1.3 (2)
C3—C31—C32—C37	−175.29 (14)	C5—C51—C52—C53	−179.67 (15)
C37—C32—C33—C34	1.4 (2)	C51—C52—C53—C54	0.0 (3)
C31—C32—C33—C34	−179.72 (16)	C52—C53—C54—C55	−1.2 (3)
C32—C33—C34—C35	0.3 (3)	C53—C54—C55—C56	1.1 (3)
C33—C34—C35—C36	−1.3 (3)	C54—C55—C56—C51	0.3 (3)
C34—C35—C36—C37	0.5 (3)	C52—C51—C56—C55	−1.4 (2)
C35—C36—C37—N1	179.66 (18)	C5—C51—C56—C55	179.51 (14)
C35—C36—C37—C32	1.3 (3)	C31—C38—N1—C37	0.49 (18)
C33—C32—C37—N1	179.05 (14)	C36—C37—N1—C38	−178.77 (17)
C31—C32—C37—N1	−0.11 (17)	C32—C37—N1—C38	−0.22 (18)
C33—C32—C37—C36	−2.3 (2)	C2—C3—O1—C4	5.08 (16)
C31—C32—C37—C36	178.58 (15)	C31—C3—O1—C4	−176.50 (12)
C32—C31—C38—N1	−0.55 (17)	C41—C4—O1—C3	108.41 (13)
C3—C31—C38—N1	175.17 (14)	C5—C4—O1—C3	−12.65 (15)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1,C31,C32,C37,C38 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C33—H33···O1	0.93	2.56	3.040 (2)	112
C56—H56···O2ⁱ	0.93	2.45	3.330 (2)	158
N1—H1···N2ⁱⁱ	0.86	2.20	3.037 (2)	163
C43—H43···Cg1ⁱⁱⁱ	0.93	2.96	3.410 (2)	112

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

Experimental details

Crystal data
Chemical formula	C₂₆H₁₈N₂O₂
M_r	390.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.4027 (5), 8.3722 (4), 19.7472 (8)
β (°)	107.570 (2)
V (Å³)	1954.85 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.17 × 0.14 × 0.13

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	20260, 4403, 3021
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.646

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.117, 1.02
No. of reflections	4403
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.15

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