16-Methyl-11-(2-methyl-phen-yl)-14-phenyl-8,12-dioxa-14,15-di-aza-tetra-cyclo-[8.7.0.0(2,7).0(13,17)]hepta-deca-2(7),3,5,13(17),15-penta-ene-10-carbo-nitrile.

In the title compound, C28H23N3O2, the pyrazole ring makes a dihedral angle of 16.90 (6)° with the phenyl ring to which it is attached. Both di-hydro-pyran rings exhibit half-chair conformations. Intramolecular C-H⋯O interactions generate S(6) and S(8) ring motifs. In the crystal, weak C-H⋯O and C-H⋯π interactions occur.

Related literature

For the biological activities of 4H-chromenes see: Cai et al. (2006 ▶); Gabor (1988 ▶); Brooks (1998 ▶); Valenti et al. (1993 ▶); Tang et al. (2007 ▶). For related structures see: Ponnusamy et al. (2013 ▶); Kanchanadevi et al. (2013 ▶).

Experimental

Crystal data

C28H23N3O2

M = 433.49

Triclinic,

a = 9.021 (5) Å

b = 9.604 (5) Å

c = 15.254 (5) Å

α = 72.720 (5)°

β = 76.997 (5)°

γ = 63.875 (5)°

V = 1126.1 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.980, T max = 0.983

20066 measured reflections

4154 independent reflections

3085 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.133

S = 1.03

4154 reflections

300 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813029905/bt6941sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813029905/bt6941Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813029905/bt6941Isup3.cml

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

C28H23N3O2	Z = 2
Mr = 433.49	F(000) = 456
Triclinic, P1	Dx = 1.278 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.021 (5) Å	Cell parameters from 9100 reflections
b = 9.604 (5) Å	θ = 2.4–25.4°
c = 15.254 (5) Å	µ = 0.08 mm−1
α = 72.720 (5)°	T = 295 K
β = 76.997 (5)°	Block, colourless
γ = 63.875 (5)°	0.30 × 0.20 × 0.20 mm
V = 1126.1 (9) Å3

Bruker APEXII CCD diffractometer	4154 independent reflections
Radiation source: fine-focus sealed tube	3085 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 0 pixels mm-1	θmax = 25.4°, θmin = 2.4°
ω and φ scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→11
Tmin = 0.980, Tmax = 0.983	l = −18→18
20066 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0709P)2 + 0.226P] where P = (Fo2 + 2Fc2)/3
4154 reflections	(Δ/σ)max = 0.003
300 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.6925 (2)	−0.0765 (2)	0.56488 (12)	0.0419 (4)
C2	0.8398 (3)	−0.0745 (3)	0.51420 (15)	0.0625 (6)
H2	0.8788	−0.0018	0.5180	0.075*
C3	0.9283 (3)	−0.1800 (3)	0.45841 (16)	0.0732 (7)
H3	1.0279	−0.1791	0.4250	0.088*
C4	0.8716 (3)	−0.2860 (3)	0.45144 (15)	0.0688 (6)
H4	0.9324	−0.3577	0.4138	0.083*
C5	0.7238 (3)	−0.2861 (3)	0.50042 (14)	0.0614 (6)
H5	0.6840	−0.3572	0.4951	0.074*
C6	0.6334 (2)	−0.1812 (2)	0.55777 (13)	0.0491 (5)
H6	0.5337	−0.1820	0.5910	0.059*
C7	0.4881 (2)	0.0363 (2)	0.69459 (11)	0.0364 (4)
C8	0.28622 (19)	−0.0390 (2)	0.79451 (11)	0.0349 (4)
H8	0.1918	0.0427	0.7618	0.042*
C9	0.2496 (2)	−0.1847 (2)	0.83666 (11)	0.0363 (4)
C10	0.3741 (2)	−0.3256 (2)	0.87619 (13)	0.0441 (4)
H10	0.4801	−0.3293	0.8723	0.053*
C11	0.3442 (3)	−0.4593 (2)	0.92089 (13)	0.0507 (5)
H11	0.4293	−0.5527	0.9463	0.061*
C12	0.1869 (3)	−0.4537 (2)	0.92762 (13)	0.0519 (5)
H12	0.1640	−0.5421	0.9598	0.062*
C13	0.0645 (2)	−0.3173 (2)	0.88667 (13)	0.0493 (5)
H13	−0.0404	−0.3160	0.8903	0.059*
C14	0.0913 (2)	−0.1809 (2)	0.83990 (12)	0.0415 (4)
C15	0.31559 (19)	0.03344 (19)	0.86501 (11)	0.0351 (4)
C16	0.1756 (2)	0.0616 (2)	0.94426 (12)	0.0425 (4)
H16A	0.1724	−0.0396	0.9793	0.051*
H16B	0.1976	0.1088	0.9854	0.051*
C17	0.0135 (2)	0.3002 (2)	0.84581 (12)	0.0435 (4)
C18	−0.1443 (2)	0.4159 (3)	0.82910 (15)	0.0598 (6)
H18	−0.2374	0.4008	0.8635	0.072*
C19	−0.1631 (3)	0.5517 (3)	0.76227 (16)	0.0664 (6)
H19	−0.2689	0.6287	0.7509	0.080*
C20	−0.0261 (3)	0.5744 (2)	0.71199 (15)	0.0616 (6)
H20	−0.0388	0.6670	0.6665	0.074*
C21	0.1304 (2)	0.4599 (2)	0.72885 (13)	0.0488 (5)
H21	0.2226	0.4767	0.6944	0.059*
C22	0.1540 (2)	0.3200 (2)	0.79597 (12)	0.0388 (4)
C23	0.3274 (2)	0.19451 (19)	0.81404 (11)	0.0365 (4)
H23	0.3724	0.2263	0.8540	0.044*
C24	0.4482 (2)	0.1651 (2)	0.72960 (12)	0.0386 (4)
C25	0.5545 (2)	0.2371 (2)	0.67479 (14)	0.0475 (5)
C26	0.5733 (3)	0.3799 (3)	0.68336 (19)	0.0751 (7)
H26A	0.6859	0.3688	0.6632	0.113*
H26B	0.5462	0.3883	0.7467	0.113*
H26C	0.4999	0.4741	0.6457	0.113*
C27	0.4710 (2)	−0.0739 (2)	0.90646 (12)	0.0402 (4)
C28	−0.0485 (2)	−0.0383 (3)	0.79348 (15)	0.0606 (6)
H28A	−0.1447	−0.0620	0.8035	0.091*
H28B	−0.0153	−0.0130	0.7284	0.091*
H28C	−0.0746	0.0510	0.8190	0.091*
N1	0.64918 (19)	0.16067 (19)	0.61013 (11)	0.0513 (4)
N2	0.60710 (17)	0.03354 (17)	0.62256 (10)	0.0422 (4)
N3	0.5899 (2)	−0.1541 (2)	0.94037 (13)	0.0589 (5)
O1	0.43131 (14)	−0.08065 (13)	0.72675 (8)	0.0395 (3)
O2	0.01940 (14)	0.16371 (16)	0.91092 (9)	0.0495 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0371 (9)	0.0432 (10)	0.0369 (9)	−0.0118 (8)	0.0005 (7)	−0.0076 (8)
C2	0.0514 (12)	0.0729 (15)	0.0632 (14)	−0.0294 (11)	0.0194 (10)	−0.0275 (12)
C3	0.0598 (14)	0.0866 (17)	0.0643 (15)	−0.0265 (13)	0.0232 (11)	−0.0311 (13)
C4	0.0696 (15)	0.0742 (16)	0.0488 (12)	−0.0129 (13)	0.0042 (11)	−0.0275 (11)
C5	0.0709 (15)	0.0600 (13)	0.0532 (12)	−0.0212 (11)	−0.0067 (11)	−0.0209 (10)
C6	0.0444 (11)	0.0536 (12)	0.0445 (11)	−0.0166 (9)	−0.0011 (8)	−0.0117 (9)
C7	0.0306 (8)	0.0361 (9)	0.0403 (9)	−0.0156 (7)	0.0010 (7)	−0.0058 (7)
C8	0.0275 (8)	0.0383 (9)	0.0359 (9)	−0.0132 (7)	0.0016 (7)	−0.0081 (7)
C9	0.0366 (9)	0.0412 (10)	0.0344 (9)	−0.0197 (8)	0.0016 (7)	−0.0109 (7)
C10	0.0400 (10)	0.0418 (10)	0.0521 (11)	−0.0182 (8)	−0.0041 (8)	−0.0106 (8)
C11	0.0577 (12)	0.0386 (10)	0.0553 (12)	−0.0197 (9)	−0.0070 (9)	−0.0086 (9)
C12	0.0688 (14)	0.0495 (12)	0.0483 (11)	−0.0383 (11)	0.0032 (10)	−0.0104 (9)
C13	0.0516 (11)	0.0625 (13)	0.0480 (11)	−0.0372 (11)	0.0039 (9)	−0.0171 (10)
C14	0.0411 (10)	0.0519 (11)	0.0384 (9)	−0.0252 (9)	0.0000 (7)	−0.0128 (8)
C15	0.0301 (8)	0.0373 (9)	0.0364 (9)	−0.0130 (7)	−0.0023 (7)	−0.0081 (7)
C16	0.0382 (10)	0.0479 (10)	0.0391 (10)	−0.0161 (8)	−0.0009 (7)	−0.0108 (8)
C17	0.0371 (10)	0.0483 (11)	0.0419 (10)	−0.0122 (8)	−0.0021 (8)	−0.0154 (8)
C18	0.0355 (10)	0.0707 (15)	0.0603 (13)	−0.0067 (10)	−0.0023 (9)	−0.0221 (11)
C19	0.0480 (13)	0.0658 (15)	0.0627 (14)	0.0032 (11)	−0.0133 (11)	−0.0186 (12)
C20	0.0655 (14)	0.0455 (12)	0.0531 (12)	−0.0026 (10)	−0.0127 (11)	−0.0085 (9)
C21	0.0504 (11)	0.0427 (11)	0.0465 (11)	−0.0125 (9)	−0.0033 (9)	−0.0120 (9)
C22	0.0380 (9)	0.0386 (10)	0.0391 (9)	−0.0115 (8)	−0.0027 (7)	−0.0151 (8)
C23	0.0324 (9)	0.0377 (9)	0.0408 (9)	−0.0142 (8)	−0.0021 (7)	−0.0120 (7)
C24	0.0325 (9)	0.0379 (10)	0.0446 (10)	−0.0153 (8)	0.0011 (7)	−0.0100 (8)
C25	0.0408 (10)	0.0448 (11)	0.0582 (12)	−0.0222 (9)	0.0047 (9)	−0.0129 (9)
C26	0.0767 (16)	0.0669 (15)	0.0984 (19)	−0.0493 (13)	0.0190 (14)	−0.0309 (14)
C27	0.0385 (10)	0.0411 (10)	0.0435 (10)	−0.0179 (9)	−0.0030 (8)	−0.0111 (8)
C28	0.0456 (12)	0.0736 (15)	0.0664 (14)	−0.0299 (11)	−0.0131 (10)	−0.0066 (11)
N1	0.0452 (9)	0.0505 (10)	0.0600 (10)	−0.0278 (8)	0.0125 (8)	−0.0148 (8)
N2	0.0373 (8)	0.0423 (8)	0.0448 (8)	−0.0190 (7)	0.0083 (6)	−0.0114 (7)
N3	0.0509 (10)	0.0516 (10)	0.0744 (12)	−0.0159 (9)	−0.0222 (9)	−0.0108 (9)
O1	0.0375 (6)	0.0400 (7)	0.0420 (7)	−0.0194 (5)	0.0074 (5)	−0.0133 (5)
O2	0.0323 (7)	0.0569 (8)	0.0525 (8)	−0.0161 (6)	0.0036 (6)	−0.0118 (6)

C1—C6	1.367 (3)	C15—C16	1.528 (2)
C1—C2	1.384 (3)	C15—C23	1.550 (2)
C1—N2	1.420 (2)	C16—O2	1.420 (2)
C2—C3	1.372 (3)	C16—H16A	0.9700
C2—H2	0.9300	C16—H16B	0.9700
C3—C4	1.363 (3)	C17—O2	1.377 (2)
C3—H3	0.9300	C17—C22	1.383 (3)
C4—C5	1.374 (3)	C17—C18	1.389 (3)
C4—H4	0.9300	C18—C19	1.364 (3)
C5—C6	1.387 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.369 (3)
C6—H6	0.9300	C19—H19	0.9300
C7—N2	1.349 (2)	C20—C21	1.378 (3)
C7—O1	1.354 (2)	C20—H20	0.9300
C7—C24	1.363 (2)	C21—C22	1.388 (3)
C8—O1	1.4550 (19)	C21—H21	0.9300
C8—C9	1.502 (2)	C22—C23	1.520 (2)
C8—C15	1.564 (2)	C23—C24	1.497 (2)
C8—H8	0.9800	C23—H23	0.9800
C9—C10	1.392 (3)	C24—C25	1.406 (2)
C9—C14	1.403 (2)	C25—N1	1.319 (2)
C10—C11	1.375 (3)	C25—C26	1.500 (3)
C10—H10	0.9300	C26—H26A	0.9600
C11—C12	1.377 (3)	C26—H26B	0.9600
C11—H11	0.9300	C26—H26C	0.9600
C12—C13	1.370 (3)	C27—N3	1.139 (2)
C12—H12	0.9300	C28—H28A	0.9600
C13—C14	1.389 (3)	C28—H28B	0.9600
C13—H13	0.9300	C28—H28C	0.9600
C14—C28	1.508 (3)	N1—N2	1.382 (2)
C15—C27	1.472 (2)
C6—C1—C2	120.00 (18)	C15—C16—H16A	109.4
C6—C1—N2	122.32 (16)	O2—C16—H16B	109.4
C2—C1—N2	117.68 (17)	C15—C16—H16B	109.4
C3—C2—C1	120.0 (2)	H16A—C16—H16B	108.0
C3—C2—H2	120.0	O2—C17—C22	123.01 (16)
C1—C2—H2	120.0	O2—C17—C18	115.77 (17)
C4—C3—C2	120.6 (2)	C22—C17—C18	121.14 (19)
C4—C3—H3	119.7	C19—C18—C17	120.1 (2)
C2—C3—H3	119.7	C19—C18—H18	119.9
C3—C4—C5	119.5 (2)	C17—C18—H18	119.9
C3—C4—H4	120.3	C18—C19—C20	120.0 (2)
C5—C4—H4	120.3	C18—C19—H19	120.0
C4—C5—C6	120.7 (2)	C20—C19—H19	120.0
C4—C5—H5	119.7	C19—C20—C21	119.9 (2)
C6—C5—H5	119.7	C19—C20—H20	120.1
C1—C6—C5	119.27 (19)	C21—C20—H20	120.1
C1—C6—H6	120.4	C20—C21—C22	121.67 (19)
C5—C6—H6	120.4	C20—C21—H21	119.2
N2—C7—O1	122.29 (15)	C22—C21—H21	119.2
N2—C7—C24	109.30 (15)	C17—C22—C21	117.23 (17)
O1—C7—C24	128.28 (15)	C17—C22—C23	121.57 (16)
O1—C8—C9	107.74 (13)	C21—C22—C23	121.20 (16)
O1—C8—C15	109.91 (13)	C24—C23—C22	115.21 (14)
C9—C8—C15	114.90 (14)	C24—C23—C15	106.57 (13)
O1—C8—H8	108.0	C22—C23—C15	108.94 (13)
C9—C8—H8	108.0	C24—C23—H23	108.7
C15—C8—H8	108.0	C22—C23—H23	108.7
C10—C9—C14	119.09 (16)	C15—C23—H23	108.7
C10—C9—C8	119.30 (15)	C7—C24—C25	103.93 (15)
C14—C9—C8	121.58 (15)	C7—C24—C23	121.78 (15)
C11—C10—C9	121.61 (17)	C25—C24—C23	134.00 (16)
C11—C10—H10	119.2	N1—C25—C24	111.93 (16)
C9—C10—H10	119.2	N1—C25—C26	119.44 (17)
C10—C11—C12	119.34 (18)	C24—C25—C26	128.61 (18)
C10—C11—H11	120.3	C25—C26—H26A	109.5
C12—C11—H11	120.3	C25—C26—H26B	109.5
C13—C12—C11	119.63 (18)	H26A—C26—H26B	109.5
C13—C12—H12	120.2	C25—C26—H26C	109.5
C11—C12—H12	120.2	H26A—C26—H26C	109.5
C12—C13—C14	122.41 (17)	H26B—C26—H26C	109.5
C12—C13—H13	118.8	N3—C27—C15	177.91 (19)
C14—C13—H13	118.8	C14—C28—H28A	109.5
C13—C14—C9	117.83 (17)	C14—C28—H28B	109.5
C13—C14—C28	118.88 (16)	H28A—C28—H28B	109.5
C9—C14—C28	123.28 (16)	C14—C28—H28C	109.5
C27—C15—C16	107.11 (14)	H28A—C28—H28C	109.5
C27—C15—C23	108.72 (13)	H28B—C28—H28C	109.5
C16—C15—C23	108.72 (14)	C25—N1—N2	105.44 (14)
C27—C15—C8	110.90 (14)	C7—N2—N1	109.38 (14)
C16—C15—C8	112.16 (13)	C7—N2—C1	131.23 (15)
C23—C15—C8	109.13 (14)	N1—N2—C1	119.35 (14)
O2—C16—C15	111.34 (14)	C7—O1—C8	111.93 (12)
O2—C16—H16A	109.4	C17—O2—C16	116.17 (13)
C6—C1—C2—C3	−1.4 (3)	C20—C21—C22—C23	−179.94 (17)
N2—C1—C2—C3	179.1 (2)	C17—C22—C23—C24	139.64 (17)
C1—C2—C3—C4	0.8 (4)	C21—C22—C23—C24	−40.7 (2)
C2—C3—C4—C5	0.4 (4)	C17—C22—C23—C15	20.0 (2)
C3—C4—C5—C6	−1.0 (4)	C21—C22—C23—C15	−160.35 (15)
C2—C1—C6—C5	0.9 (3)	C27—C15—C23—C24	71.73 (17)
N2—C1—C6—C5	−179.67 (17)	C16—C15—C23—C24	−171.97 (13)
C4—C5—C6—C1	0.3 (3)	C8—C15—C23—C24	−49.35 (16)
O1—C8—C9—C10	54.68 (19)	C27—C15—C23—C22	−163.39 (13)
C15—C8—C9—C10	−68.2 (2)	C16—C15—C23—C22	−47.10 (17)
O1—C8—C9—C14	−127.45 (16)	C8—C15—C23—C22	75.53 (16)
C15—C8—C9—C14	109.68 (17)	N2—C7—C24—C25	−1.34 (19)
C14—C9—C10—C11	−2.2 (3)	O1—C7—C24—C25	174.53 (17)
C8—C9—C10—C11	175.76 (16)	N2—C7—C24—C23	−175.98 (15)
C9—C10—C11—C12	−0.6 (3)	O1—C7—C24—C23	−0.1 (3)
C10—C11—C12—C13	2.6 (3)	C22—C23—C24—C7	−101.70 (19)
C11—C12—C13—C14	−1.7 (3)	C15—C23—C24—C7	19.3 (2)
C12—C13—C14—C9	−1.1 (3)	C22—C23—C24—C25	85.5 (2)
C12—C13—C14—C28	177.50 (18)	C15—C23—C24—C25	−153.51 (19)
C10—C9—C14—C13	3.0 (2)	C7—C24—C25—N1	1.3 (2)
C8—C9—C14—C13	−174.90 (15)	C23—C24—C25—N1	174.98 (18)
C10—C9—C14—C28	−175.56 (17)	C7—C24—C25—C26	−176.9 (2)
C8—C9—C14—C28	6.6 (3)	C23—C24—C25—C26	−3.3 (4)
O1—C8—C15—C27	−53.68 (18)	C24—C25—N1—N2	−0.8 (2)
C9—C8—C15—C27	68.02 (18)	C26—C25—N1—N2	177.66 (18)
O1—C8—C15—C16	−173.39 (13)	O1—C7—N2—N1	−175.21 (15)
C9—C8—C15—C16	−51.69 (19)	C24—C7—N2—N1	0.96 (19)
O1—C8—C15—C23	66.07 (16)	O1—C7—N2—C1	2.1 (3)
C9—C8—C15—C23	−172.23 (13)	C24—C7—N2—C1	178.30 (17)
C27—C15—C16—O2	−179.60 (14)	C25—N1—N2—C7	−0.1 (2)
C23—C15—C16—O2	63.08 (17)	C25—N1—N2—C1	−177.82 (16)
C8—C15—C16—O2	−57.70 (19)	C6—C1—N2—C7	18.8 (3)
O2—C17—C18—C19	−176.47 (18)	C2—C1—N2—C7	−161.74 (19)
C22—C17—C18—C19	0.3 (3)	C6—C1—N2—N1	−164.07 (17)
C17—C18—C19—C20	−0.4 (3)	C2—C1—N2—N1	15.4 (3)
C18—C19—C20—C21	0.2 (3)	N2—C7—O1—C8	−170.88 (15)
C19—C20—C21—C22	0.2 (3)	C24—C7—O1—C8	13.7 (2)
O2—C17—C22—C21	176.57 (15)	C9—C8—O1—C7	−171.15 (13)
C18—C17—C22—C21	0.0 (3)	C15—C8—O1—C7	−45.26 (17)
O2—C17—C22—C23	−3.8 (3)	C22—C17—O2—C16	17.4 (2)
C18—C17—C22—C23	179.67 (16)	C18—C17—O2—C16	−165.84 (16)
C20—C21—C22—C17	−0.3 (3)	C15—C16—O2—C17	−47.30 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N1	0.93	2.42	2.759 (3)	102
C6—H6···O1	0.93	2.37	2.952 (2)	120
C28—H28C···O2	0.96	2.47	3.310 (3)	146
C16—H16A···O2i	0.97	2.56	3.380 (2)	143
C20—H20···Cg1ii	0.96	2.86	3.567	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1	0.93	2.37	2.952 (2)	120
C28—H28C⋯O2	0.96	2.47	3.310 (3)	146
C16—H16A⋯O2i	0.97	2.56	3.380 (2)	143
C20—H20⋯Cg1ii	0.96	2.86	3.567 (3)	134

Symmetry codes: (i) ; (ii) .