Spiro­[5-carbo­methoxy-2-(4-methoxy­phenyl)-4-(4-methyl­phenyl)­pyrrolidine-3,3′-chroman-4′-one]

In the title compound, C₂₈H₂₇NO₅, the pyran ring in the chroman-4-one moiety adopts a sofa conformation and the pyrrolidine ring adopts an envelope conformation. The chromanone moiety makes a dihedral angle of 79.1 (1)° with the mean plane passing through the pyrrolidine ring. In the crystal structure, the mol­ecules in the crystal lattice are stabilized by C—H...O intermolecular interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.064
• wR factor = 0.200
• Data-to-parameter ratio = 13.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_420  Alert C D-H Without Acceptor       N(1)   -   H(1)              ?


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and BIOSYM INSIGHT-II (MSI, 1995); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1983b, 1995).

Spiro[5-carbomethoxy-2-(4-methoxyphenyl)-4-(4-methylphenyl)pyrrolidine-3,3'- chroman-4'-one]

Crystal data

C28H27NO5	F(000) = 968
Mr = 457.51	Dx = 1.289 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.4779 (6) Å	Cell parameters from 25 reflections
b = 18.0879 (19) Å	θ = 19.7–28.2°
c = 10.4580 (19) Å	µ = 0.09 mm^−1
β = 92.782 (9)°	T = 293 K
V = 2357.6 (5) Å^3	Prism, colourless
Z = 4	0.32 × 0.25 × 0.18 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.079
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 1.6°
Graphite monochromator	h = 0→14
ω/2θ scans	k = −21→0
4342 measured reflections	l = −12→12
4144 independent reflections	3 standard reflections every 100 reflections
2306 reflections with I > 2σ(I)	intensity decay: 1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.064	H-atom parameters constrained
wR(F^2) = 0.200	w = 1/[σ^2(Fo^2) + (0.1092P)^2 + 0.3704P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.005
4144 reflections	Δρmax = 0.34 e Å^−3
310 parameters	Δρmin = −0.41 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.2774 (2)	−0.26246 (13)	0.7940 (3)	0.0540 (7)
H1	0.2497	−0.3050	0.7761	0.065*
O1	0.25013 (19)	−0.11143 (13)	0.5449 (2)	0.0628 (7)
O2	0.21895 (19)	−0.03912 (13)	0.9101 (2)	0.0642 (7)
O3	−0.2169 (2)	−0.1963 (2)	0.6407 (4)	0.1211 (13)
O4	0.4439 (2)	−0.32473 (18)	0.6358 (3)	0.0967 (10)
O5	0.5293 (2)	−0.33171 (16)	0.8231 (2)	0.0832 (9)
C1	0.2412 (2)	−0.09030 (16)	0.6545 (3)	0.0435 (7)
C2	0.2936 (2)	−0.13159 (15)	0.7686 (3)	0.0397 (7)
C3	0.3160 (3)	−0.07462 (18)	0.8747 (3)	0.0518 (8)
H3A	0.3494	−0.0990	0.9491	0.062*
H3B	0.3656	−0.0377	0.8455	0.062*
C4	0.0974 (3)	0.0540 (2)	0.8404 (5)	0.0882 (14)
H4	0.0878	0.0668	0.9253	0.106*
C5	0.0444 (4)	0.0918 (2)	0.7423 (7)	0.1031 (18)
H5	−0.0016	0.1304	0.7610	0.124*
C6	0.0585 (4)	0.0733 (3)	0.6183 (6)	0.1015 (17)
H6	0.0232	0.1000	0.5530	0.122*
C7	0.1239 (3)	0.0162 (2)	0.5886 (4)	0.0728 (11)
H7	0.1321	0.0039	0.5032	0.087*
C8	0.1788 (2)	−0.02414 (17)	0.6848 (3)	0.0512 (8)
C9	0.1653 (3)	−0.00345 (18)	0.8107 (4)	0.0592 (9)
C10	0.2187 (2)	−0.19416 (16)	0.8197 (3)	0.0468 (8)
H10	0.2168	−0.1886	0.9128	0.056*
C11	0.1040 (2)	−0.19614 (17)	0.7657 (3)	0.0503 (8)
C12	0.0243 (3)	−0.1614 (2)	0.8323 (4)	0.0722 (11)
H12	0.0428	−0.1376	0.9091	0.087*
C13	−0.0805 (3)	−0.1615 (3)	0.7876 (5)	0.0904 (14)
H13	−0.1324	−0.1372	0.8328	0.108*
C14	−0.1090 (3)	−0.1977 (2)	0.6749 (5)	0.0783 (12)
C15	−0.0327 (3)	−0.2302 (2)	0.6067 (4)	0.0709 (11)
H15	−0.0514	−0.2527	0.5288	0.085*
C16	0.0746 (3)	−0.23004 (19)	0.6530 (4)	0.0602 (9)
H16	0.1264	−0.2534	0.6063	0.072*
C17	−0.2527 (4)	−0.2328 (3)	0.5296 (6)	0.135 (2)
H17A	−0.2148	−0.2145	0.4585	0.202*
H17B	−0.3282	−0.2242	0.5145	0.202*
H17C	−0.2398	−0.2849	0.5392	0.202*
C18	0.3917 (2)	−0.24459 (16)	0.8044 (3)	0.0472 (8)
H18	0.4163	−0.2374	0.8940	0.057*
C19	0.4554 (3)	−0.30403 (18)	0.7423 (3)	0.0512 (8)
C20	0.5985 (4)	−0.3881 (3)	0.7722 (5)	0.120 (2)
H20A	0.5553	−0.4261	0.7314	0.181*
H20B	0.6423	−0.4093	0.8408	0.181*
H20C	0.6437	−0.3662	0.7108	0.181*
C21	0.3955 (2)	−0.17283 (16)	0.7299 (3)	0.0431 (7)
H21	0.3840	−0.1858	0.6393	0.052*
C22	0.4972 (2)	−0.12743 (16)	0.7406 (3)	0.0430 (7)
C23	0.5280 (3)	−0.08737 (19)	0.6357 (3)	0.0540 (8)
H23	0.4899	−0.0932	0.5578	0.065*
C24	0.6131 (3)	−0.0394 (2)	0.6434 (3)	0.0604 (9)
H24	0.6308	−0.0131	0.5710	0.073*
C25	0.6740 (3)	−0.02925 (18)	0.7580 (3)	0.0533 (8)
C26	0.6448 (3)	−0.07026 (18)	0.8610 (3)	0.0530 (8)
H26	0.6842	−0.0654	0.9384	0.064*
C27	0.5589 (2)	−0.11856 (19)	0.8538 (3)	0.0513 (8)
H27	0.5421	−0.1455	0.9259	0.062*
C28	0.7657 (3)	0.0243 (2)	0.7666 (4)	0.0789 (12)
H28A	0.7612	0.0538	0.8424	0.118*
H28B	0.7625	0.0558	0.6927	0.118*
H28C	0.8323	−0.0024	0.7702	0.118*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0494 (16)	0.0384 (14)	0.0733 (19)	−0.0009 (12)	−0.0044 (13)	0.0009 (14)
O1	0.0748 (16)	0.0749 (16)	0.0380 (13)	0.0086 (13)	−0.0045 (11)	0.0054 (12)
O2	0.0606 (15)	0.0722 (15)	0.0589 (14)	0.0160 (13)	−0.0060 (12)	−0.0247 (13)
O3	0.0591 (19)	0.130 (3)	0.171 (4)	0.0167 (19)	−0.023 (2)	−0.018 (3)
O4	0.116 (2)	0.109 (2)	0.0627 (18)	0.0447 (19)	−0.0162 (16)	−0.0291 (17)
O5	0.0907 (19)	0.0881 (19)	0.0692 (17)	0.0472 (16)	−0.0133 (14)	−0.0074 (15)
C1	0.0427 (17)	0.0421 (17)	0.0450 (19)	−0.0058 (14)	−0.0039 (14)	0.0049 (14)
C2	0.0443 (17)	0.0394 (15)	0.0345 (15)	0.0004 (13)	−0.0064 (13)	−0.0012 (13)
C3	0.0499 (18)	0.0574 (19)	0.0471 (18)	0.0075 (16)	−0.0068 (15)	−0.0103 (16)
C4	0.064 (2)	0.073 (3)	0.126 (4)	0.014 (2)	−0.016 (3)	−0.042 (3)
C5	0.068 (3)	0.056 (3)	0.181 (6)	0.023 (2)	−0.035 (3)	−0.024 (3)
C6	0.084 (3)	0.061 (3)	0.156 (5)	0.012 (2)	−0.035 (3)	0.017 (3)
C7	0.065 (2)	0.059 (2)	0.092 (3)	0.006 (2)	−0.014 (2)	0.023 (2)
C8	0.0437 (18)	0.0414 (17)	0.068 (2)	−0.0039 (14)	−0.0080 (16)	0.0041 (16)
C9	0.0458 (19)	0.0482 (19)	0.082 (3)	0.0034 (16)	−0.0125 (18)	−0.0114 (19)
C10	0.0508 (18)	0.0480 (18)	0.0415 (17)	0.0008 (15)	0.0003 (14)	0.0059 (14)
C11	0.0462 (19)	0.0451 (18)	0.060 (2)	−0.0023 (15)	0.0029 (16)	0.0082 (16)
C12	0.056 (2)	0.084 (3)	0.077 (3)	0.005 (2)	0.0103 (19)	−0.002 (2)
C13	0.051 (2)	0.103 (3)	0.118 (4)	0.013 (2)	0.007 (2)	−0.007 (3)
C14	0.045 (2)	0.077 (3)	0.111 (4)	0.002 (2)	−0.012 (2)	0.011 (3)
C15	0.062 (2)	0.063 (2)	0.086 (3)	−0.002 (2)	−0.018 (2)	−0.005 (2)
C16	0.055 (2)	0.052 (2)	0.073 (2)	−0.0009 (16)	0.0015 (18)	−0.0026 (18)
C17	0.083 (4)	0.130 (5)	0.185 (6)	−0.006 (3)	−0.059 (4)	−0.016 (5)
C18	0.0504 (19)	0.0493 (18)	0.0410 (17)	0.0070 (15)	−0.0061 (14)	0.0037 (15)
C19	0.058 (2)	0.0504 (19)	0.0440 (19)	0.0092 (16)	−0.0077 (16)	0.0015 (16)
C20	0.125 (4)	0.123 (4)	0.113 (4)	0.086 (4)	0.000 (3)	−0.005 (3)
C21	0.0478 (17)	0.0462 (17)	0.0348 (16)	0.0016 (14)	−0.0031 (13)	−0.0034 (13)
C22	0.0389 (16)	0.0493 (17)	0.0405 (17)	0.0024 (14)	−0.0009 (13)	0.0001 (14)
C23	0.0523 (19)	0.072 (2)	0.0368 (18)	−0.0040 (18)	−0.0051 (14)	0.0043 (16)
C24	0.062 (2)	0.072 (2)	0.047 (2)	−0.0083 (19)	0.0023 (17)	0.0171 (18)
C25	0.0492 (18)	0.060 (2)	0.051 (2)	−0.0049 (16)	0.0036 (15)	0.0037 (17)
C26	0.0494 (19)	0.064 (2)	0.0453 (19)	−0.0066 (17)	−0.0057 (15)	0.0015 (17)
C27	0.0495 (19)	0.063 (2)	0.0408 (18)	−0.0025 (17)	−0.0029 (15)	0.0121 (16)
C28	0.072 (3)	0.092 (3)	0.072 (3)	−0.025 (2)	−0.001 (2)	0.004 (2)

Geometric parameters (Å, º)

N1—C18	1.462 (4)	C12—H12	0.9300
N1—C10	1.467 (4)	C13—C14	1.380 (6)
N1—H1	0.8600	C13—H13	0.9300
O1—C1	1.219 (3)	C14—C15	1.351 (6)
O2—C9	1.370 (4)	C15—C16	1.402 (5)
O2—C3	1.435 (4)	C15—H15	0.9300
O3—C14	1.377 (5)	C16—H16	0.9300
O3—C17	1.390 (6)	C17—H17A	0.9600
O4—C19	1.177 (4)	C17—H17B	0.9600
O5—C19	1.320 (4)	C17—H17C	0.9600
O5—C20	1.455 (5)	C18—C19	1.503 (4)
C1—C8	1.470 (4)	C18—C21	1.516 (4)
C1—C2	1.528 (4)	C18—H18	0.9800
C2—C3	1.530 (4)	C20—H20A	0.9600
C2—C21	1.545 (4)	C20—H20B	0.9600
C2—C10	1.578 (4)	C20—H20C	0.9600
C3—H3A	0.9700	C21—C22	1.510 (4)
C3—H3B	0.9700	C21—H21	0.9800
C4—C5	1.375 (7)	C22—C23	1.385 (4)
C4—C9	1.387 (5)	C22—C27	1.390 (4)
C4—H4	0.9300	C23—C24	1.371 (5)
C5—C6	1.359 (7)	C23—H23	0.9300
C5—H5	0.9300	C24—C25	1.399 (5)
C6—C7	1.363 (6)	C24—H24	0.9300
C6—H6	0.9300	C25—C26	1.372 (4)
C7—C8	1.395 (5)	C25—C28	1.498 (5)
C7—H7	0.9300	C26—C27	1.382 (4)
C8—C9	1.387 (5)	C26—H26	0.9300
C10—C11	1.514 (4)	C27—H27	0.9300
C10—H10	0.9800	C28—H28A	0.9600
C11—C16	1.362 (5)	C28—H28B	0.9600
C11—C12	1.392 (5)	C28—H28C	0.9600
C12—C13	1.368 (5)
C18—N1—C10	107.1 (2)	C14—C15—C16	120.1 (4)
C18—N1—H1	126.5	C14—C15—H15	119.9
C10—N1—H1	126.5	C16—C15—H15	119.9
C9—O2—C3	113.7 (3)	C11—C16—C15	120.8 (3)
C14—O3—C17	118.6 (4)	C11—C16—H16	119.6
C19—O5—C20	116.1 (3)	C15—C16—H16	119.6
O1—C1—C8	122.1 (3)	O3—C17—H17A	109.5
O1—C1—C2	121.7 (3)	O3—C17—H17B	109.5
C8—C1—C2	116.1 (3)	H17A—C17—H17B	109.5
C1—C2—C3	107.1 (2)	O3—C17—H17C	109.5
C1—C2—C21	111.0 (2)	H17A—C17—H17C	109.5
C3—C2—C21	113.1 (2)	H17B—C17—H17C	109.5
C1—C2—C10	112.1 (2)	N1—C18—C19	110.1 (3)
C3—C2—C10	109.1 (2)	N1—C18—C21	101.9 (2)
C21—C2—C10	104.6 (2)	C19—C18—C21	111.1 (2)
O2—C3—C2	111.2 (2)	N1—C18—H18	111.2
O2—C3—H3A	109.4	C19—C18—H18	111.2
C2—C3—H3A	109.4	C21—C18—H18	111.2
O2—C3—H3B	109.4	O4—C19—O5	122.3 (3)
C2—C3—H3B	109.4	O4—C19—C18	126.5 (3)
H3A—C3—H3B	108.0	O5—C19—C18	111.2 (3)
C5—C4—C9	118.9 (5)	O5—C20—H20A	109.5
C5—C4—H4	120.6	O5—C20—H20B	109.5
C9—C4—H4	120.6	H20A—C20—H20B	109.5
C6—C5—C4	120.6 (4)	O5—C20—H20C	109.5
C6—C5—H5	119.7	H20A—C20—H20C	109.5
C4—C5—H5	119.7	H20B—C20—H20C	109.5
C5—C6—C7	120.8 (5)	C22—C21—C18	118.3 (2)
C5—C6—H6	119.6	C22—C21—C2	114.6 (2)
C7—C6—H6	119.6	C18—C21—C2	103.4 (2)
C6—C7—C8	120.7 (5)	C22—C21—H21	106.6
C6—C7—H7	119.7	C18—C21—H21	106.6
C8—C7—H7	119.7	C2—C21—H21	106.6
C9—C8—C7	117.8 (3)	C23—C22—C27	116.8 (3)
C9—C8—C1	120.9 (3)	C23—C22—C21	119.4 (3)
C7—C8—C1	121.1 (3)	C27—C22—C21	123.7 (3)
O2—C9—C8	121.1 (3)	C24—C23—C22	122.0 (3)
O2—C9—C4	117.7 (4)	C24—C23—H23	119.0
C8—C9—C4	121.2 (4)	C22—C23—H23	119.0
N1—C10—C11	112.5 (3)	C23—C24—C25	121.4 (3)
N1—C10—C2	103.5 (2)	C23—C24—H24	119.3
C11—C10—C2	117.1 (2)	C25—C24—H24	119.3
N1—C10—H10	107.8	C26—C25—C24	116.6 (3)
C11—C10—H10	107.8	C26—C25—C28	122.2 (3)
C2—C10—H10	107.8	C24—C25—C28	121.2 (3)
C16—C11—C12	117.9 (3)	C25—C26—C27	122.3 (3)
C16—C11—C10	122.9 (3)	C25—C26—H26	118.9
C12—C11—C10	119.2 (3)	C27—C26—H26	118.9
C13—C12—C11	121.5 (4)	C26—C27—C22	121.0 (3)
C13—C12—H12	119.2	C26—C27—H27	119.5
C11—C12—H12	119.2	C22—C27—H27	119.5
C12—C13—C14	119.7 (4)	C25—C28—H28A	109.5
C12—C13—H13	120.2	C25—C28—H28B	109.5
C14—C13—H13	120.2	H28A—C28—H28B	109.5
C15—C14—O3	125.2 (5)	C25—C28—H28C	109.5
C15—C14—C13	119.9 (4)	H28A—C28—H28C	109.5
O3—C14—C13	114.9 (4)	H28B—C28—H28C	109.5
O1—C1—C2—C3	151.9 (3)	C17—O3—C14—C15	2.2 (7)
C8—C1—C2—C3	−28.5 (3)	C17—O3—C14—C13	−178.8 (5)
O1—C1—C2—C21	28.1 (4)	C12—C13—C14—C15	−2.8 (7)
C8—C1—C2—C21	−152.4 (2)	C12—C13—C14—O3	178.1 (4)
O1—C1—C2—C10	−88.4 (3)	O3—C14—C15—C16	−178.1 (4)
C8—C1—C2—C10	91.1 (3)	C13—C14—C15—C16	2.9 (6)
C9—O2—C3—C2	−58.7 (4)	C12—C11—C16—C15	−0.5 (5)
C1—C2—C3—O2	59.0 (3)	C10—C11—C16—C15	−179.8 (3)
C21—C2—C3—O2	−178.4 (2)	C14—C15—C16—C11	−1.3 (6)
C10—C2—C3—O2	−62.5 (3)	C10—N1—C18—C19	−163.2 (2)
C9—C4—C5—C6	−0.2 (7)	C10—N1—C18—C21	−45.3 (3)
C4—C5—C6—C7	1.2 (8)	C20—O5—C19—O4	1.8 (6)
C5—C6—C7—C8	−0.7 (7)	C20—O5—C19—C18	−178.0 (3)
C6—C7—C8—C9	−0.7 (5)	N1—C18—C19—O4	56.3 (5)
C6—C7—C8—C1	174.0 (3)	C21—C18—C19—O4	−55.8 (5)
O1—C1—C8—C9	176.7 (3)	N1—C18—C19—O5	−124.0 (3)
C2—C1—C8—C9	−2.9 (4)	C21—C18—C19—O5	123.9 (3)
O1—C1—C8—C7	2.1 (5)	N1—C18—C21—C22	167.5 (2)
C2—C1—C8—C7	−177.4 (3)	C19—C18—C21—C22	−75.3 (3)
C3—O2—C9—C8	24.1 (4)	N1—C18—C21—C2	39.6 (3)
C3—O2—C9—C4	−155.8 (3)	C19—C18—C21—C2	156.8 (2)
C7—C8—C9—O2	−178.2 (3)	C1—C2—C21—C22	87.9 (3)
C1—C8—C9—O2	7.1 (5)	C3—C2—C21—C22	−32.4 (3)
C7—C8—C9—C4	1.7 (5)	C10—C2—C21—C22	−151.0 (2)
C1—C8—C9—C4	−173.0 (3)	C1—C2—C21—C18	−141.8 (2)
C5—C4—C9—O2	178.6 (4)	C3—C2—C21—C18	97.8 (3)
C5—C4—C9—C8	−1.3 (6)	C10—C2—C21—C18	−20.8 (3)
C18—N1—C10—C11	158.7 (2)	C18—C21—C22—C23	146.5 (3)
C18—N1—C10—C2	31.3 (3)	C2—C21—C22—C23	−91.1 (3)
C1—C2—C10—N1	114.9 (3)	C18—C21—C22—C27	−38.6 (4)
C3—C2—C10—N1	−126.7 (2)	C2—C21—C22—C27	83.8 (4)
C21—C2—C10—N1	−5.4 (3)	C27—C22—C23—C24	−2.0 (5)
C1—C2—C10—C11	−9.5 (4)	C21—C22—C23—C24	173.2 (3)
C3—C2—C10—C11	109.0 (3)	C22—C23—C24—C25	0.8 (5)
C21—C2—C10—C11	−129.8 (3)	C23—C24—C25—C26	0.7 (5)
N1—C10—C11—C16	−35.7 (4)	C23—C24—C25—C28	−178.8 (3)
C2—C10—C11—C16	84.0 (4)	C24—C25—C26—C27	−0.9 (5)
N1—C10—C11—C12	144.9 (3)	C28—C25—C26—C27	178.7 (3)
C2—C10—C11—C12	−95.4 (4)	C25—C26—C27—C22	−0.4 (5)
C16—C11—C12—C13	0.5 (6)	C23—C22—C27—C26	1.8 (5)
C10—C11—C12—C13	179.9 (4)	C21—C22—C27—C26	−173.2 (3)
C11—C12—C13—C14	1.1 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O4^i	0.97	2.62	3.591 (4)	175

Symmetry code: (i) x, −y−1/2, z+1/2.