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In the title compound, C27H25NO5, the pyran ring in the chroman-4-one moiety adopts a sofa conformation and the pyrrolidine ring adopts a twisted or half-chair conformation. The chromanone moiety makes a dihedral angle of 64.3 (1)° with the mean plane passing through the pyrrolidine ring. In the crystal structure, the molecular packing is stabilized by C—H...O intermolecular interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801019961/cf6118sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801019961/cf6118Isup2.hkl
Contains datablock I

CCDC reference: 177230

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.128
  • Data-to-parameter ratio = 13.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
WEIGH_01 Alert C Extra text has been found in the _refine_ls_weighting_scheme field. This should be in the _refine_ls_weighting_details field. Weighting scheme given as calc w = 1/[\s^2^(Fo^2^)+(0.0663P)^2^+0.289 Weighting scheme identified as calc 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
2 Alert Level C = Please check

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EEXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLUTON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1983b, 1995).

Spiro[2-carbomethoxy-5-(4-methoxyphenyl)-3-phenylpyrrolidine-4,3'-chroman- 4'-one] top
Crystal data top
C27H25NO5Z = 2
Mr = 443.48F(000) = 468
Triclinic, P1Dx = 1.305 Mg m3
a = 6.709 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.958 (5) ÅCell parameters from 25 reflections
c = 17.743 (5) Åθ = 19.7–28.2°
α = 95.757 (5)°µ = 0.09 mm1
β = 94.587 (5)°T = 293 K
γ = 105.600 (5)°Prism, colourless
V = 1128.9 (11) Å30.3 × 0.2 × 0.2 mm
Data collection top
Enraf Nonius CAD-4
diffractometer
Rint = 0.012
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 1.2°
Graphite monochromatorh = 77
non–profiled ω/2θ scansk = 1111
4080 measured reflectionsl = 021
3942 independent reflections3 standard reflections every 100 reflections
2907 reflections with I > 2σ(I) intensity decay: <1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.128Calculated w = 1/[σ2(Fo2) + (0.0663P)2 + 0.2895P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
3942 reflectionsΔρmax = 0.38 e Å3
298 parametersΔρmin = 0.32 e Å3
0 restraintsExtinction correction: SHELXL
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00
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
xyzUiso*/Ueq
N10.5945 (3)0.10199 (17)0.31080 (11)0.0606 (5)
H10.54790.15080.34430.073*
O11.08592 (19)0.00170 (15)0.18918 (8)0.0538 (4)
O20.61071 (19)0.14181 (15)0.09832 (8)0.0560 (4)
O31.5532 (3)0.39572 (17)0.43084 (9)0.0777 (5)
O40.6341 (3)0.1343 (2)0.40869 (10)0.0918 (6)
O50.3010 (3)0.1489 (2)0.38026 (10)0.0889 (6)
C10.9473 (3)0.04826 (18)0.16500 (10)0.0389 (4)
C20.7473 (3)0.03427 (18)0.20210 (10)0.0401 (4)
C30.5740 (3)0.0196 (2)0.13778 (12)0.0492 (5)
H3A0.56500.06250.10190.059*
H3B0.44190.00570.15880.059*
C40.8180 (3)0.2591 (2)0.01203 (11)0.0511 (5)
H40.70890.29410.00420.061*
C50.9994 (3)0.2909 (2)0.02137 (11)0.0550 (5)
H51.01330.34750.06030.066*
C61.1617 (3)0.2389 (2)0.00282 (12)0.0551 (5)
H61.28310.25830.02090.066*
C71.1439 (3)0.1590 (2)0.06164 (11)0.0472 (5)
H71.25520.12610.07800.057*
C80.9626 (2)0.12586 (18)0.09745 (10)0.0386 (4)
C90.7977 (3)0.17475 (19)0.06983 (10)0.0417 (4)
C100.7567 (3)0.1621 (2)0.26265 (12)0.0484 (5)
H100.71550.23450.23680.058*
C110.9681 (3)0.22694 (19)0.30778 (11)0.0488 (5)
C121.1155 (3)0.3331 (2)0.28150 (13)0.0576 (5)
H121.08120.36490.23600.069*
C131.3119 (4)0.3936 (2)0.32033 (13)0.0605 (6)
H131.40700.46500.30130.073*
C141.3648 (3)0.3466 (2)0.38766 (12)0.0568 (5)
C151.2208 (4)0.2402 (2)0.41463 (12)0.0647 (6)
H151.25620.20750.45970.078*
C161.0263 (4)0.1822 (2)0.37585 (11)0.0585 (5)
H160.93140.11160.39550.070*
C171.7085 (4)0.5026 (3)0.40573 (17)0.0891 (8)
H17A1.83180.52680.44140.134*
H17B1.65920.58400.40210.134*
H17C1.74010.46990.35660.134*
C180.5230 (3)0.0507 (2)0.29445 (11)0.0472 (5)
H180.39030.07920.26160.057*
C190.4978 (3)0.1158 (2)0.36737 (12)0.0557 (5)
C200.2541 (6)0.2060 (5)0.45149 (19)0.1337 (15)
H20A0.10740.22520.45530.201*
H20B0.32970.13890.49370.201*
H20C0.29430.29140.45230.201*
C210.6936 (3)0.08766 (18)0.25113 (10)0.0405 (4)
H210.81480.07470.28860.049*
C220.6416 (3)0.23675 (19)0.21189 (10)0.0416 (4)
C230.4476 (3)0.3071 (2)0.17283 (11)0.0529 (5)
H230.34380.26140.16990.063*
C240.4065 (4)0.4439 (2)0.13825 (12)0.0634 (6)
H240.27630.48880.11190.076*
C250.5569 (4)0.5136 (2)0.14263 (14)0.0682 (6)
H250.52900.60560.11930.082*
C260.7479 (4)0.4470 (2)0.18147 (14)0.0662 (6)
H260.84990.49430.18470.079*
C270.7913 (3)0.3091 (2)0.21620 (12)0.0532 (5)
H270.92190.26510.24250.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0665 (11)0.0496 (10)0.0751 (12)0.0220 (8)0.0406 (9)0.0101 (9)
O10.0386 (7)0.0749 (9)0.0608 (8)0.0298 (7)0.0098 (6)0.0274 (7)
O20.0343 (7)0.0762 (9)0.0730 (9)0.0262 (6)0.0166 (6)0.0442 (8)
O30.0783 (11)0.0740 (11)0.0668 (10)0.0022 (9)0.0047 (9)0.0063 (8)
O40.0818 (12)0.1317 (17)0.0665 (11)0.0217 (11)0.0167 (9)0.0508 (11)
O50.0692 (11)0.1239 (15)0.0742 (11)0.0110 (10)0.0363 (9)0.0369 (11)
C10.0301 (9)0.0456 (10)0.0443 (10)0.0148 (8)0.0036 (7)0.0100 (8)
C20.0342 (9)0.0470 (10)0.0465 (10)0.0189 (8)0.0094 (7)0.0172 (8)
C30.0328 (9)0.0641 (12)0.0594 (12)0.0175 (9)0.0114 (8)0.0326 (10)
C40.0447 (11)0.0641 (12)0.0506 (11)0.0202 (9)0.0037 (9)0.0233 (10)
C50.0534 (12)0.0660 (13)0.0472 (11)0.0124 (10)0.0103 (9)0.0229 (10)
C60.0436 (11)0.0703 (13)0.0539 (12)0.0126 (10)0.0201 (9)0.0168 (10)
C70.0342 (9)0.0600 (12)0.0508 (11)0.0165 (8)0.0087 (8)0.0109 (9)
C80.0318 (9)0.0450 (10)0.0410 (9)0.0128 (7)0.0049 (7)0.0084 (8)
C90.0315 (9)0.0515 (10)0.0458 (10)0.0138 (8)0.0072 (7)0.0150 (8)
C100.0486 (11)0.0461 (10)0.0609 (12)0.0225 (9)0.0203 (9)0.0186 (9)
C110.0569 (12)0.0435 (10)0.0518 (11)0.0193 (9)0.0180 (9)0.0095 (9)
C120.0630 (13)0.0531 (12)0.0596 (13)0.0145 (10)0.0110 (10)0.0215 (10)
C130.0643 (14)0.0502 (12)0.0657 (14)0.0087 (10)0.0157 (11)0.0148 (10)
C140.0664 (14)0.0521 (12)0.0484 (12)0.0130 (10)0.0079 (10)0.0022 (9)
C150.0826 (16)0.0658 (14)0.0418 (11)0.0126 (12)0.0086 (11)0.0098 (10)
C160.0720 (14)0.0561 (12)0.0443 (11)0.0082 (11)0.0182 (10)0.0090 (9)
C170.0740 (17)0.0837 (18)0.092 (2)0.0029 (14)0.0026 (15)0.0076 (15)
C180.0455 (10)0.0516 (11)0.0498 (11)0.0167 (9)0.0166 (8)0.0129 (9)
C190.0591 (13)0.0592 (13)0.0480 (12)0.0105 (10)0.0183 (10)0.0096 (10)
C200.112 (2)0.195 (4)0.081 (2)0.005 (3)0.0513 (19)0.053 (2)
C210.0389 (9)0.0475 (10)0.0406 (10)0.0178 (8)0.0073 (7)0.0136 (8)
C220.0467 (10)0.0467 (10)0.0381 (9)0.0179 (8)0.0111 (8)0.0174 (8)
C230.0594 (13)0.0532 (12)0.0496 (11)0.0194 (10)0.0044 (9)0.0141 (9)
C240.0738 (15)0.0545 (13)0.0557 (13)0.0073 (11)0.0035 (11)0.0102 (10)
C250.0926 (18)0.0492 (12)0.0653 (14)0.0205 (13)0.0181 (13)0.0101 (11)
C260.0792 (16)0.0574 (13)0.0792 (16)0.0378 (12)0.0287 (13)0.0227 (12)
C270.0560 (12)0.0533 (12)0.0596 (12)0.0240 (10)0.0154 (10)0.0201 (10)
Geometric parameters (Å, º) top
N1—C181.457 (3)C11—C161.391 (3)
N1—C101.474 (2)C12—C131.385 (3)
N1—H10.860C12—H120.930
O1—C11.213 (2)C13—C141.381 (3)
O2—C91.360 (2)C13—H130.930
O2—C31.438 (2)C14—C151.382 (3)
O3—C141.364 (3)C15—C161.371 (3)
O3—C171.411 (3)C15—H150.930
O4—C191.191 (3)C16—H160.930
O5—C191.317 (3)C17—H17A0.960
O5—C201.460 (3)C17—H17B0.960
C1—C81.486 (2)C17—H17C0.960
C1—C21.521 (2)C18—C191.506 (3)
C2—C31.529 (3)C18—C211.532 (2)
C2—C211.545 (2)C18—H180.980
C2—C101.565 (3)C20—H20A0.960
C3—H3A0.970C20—H20B0.960
C3—H3B0.970C20—H20C0.960
C4—C51.370 (3)C21—C221.512 (3)
C4—C91.382 (3)C21—H210.980
C4—H40.930C22—C271.386 (3)
C5—C61.382 (3)C22—C231.390 (3)
C5—H50.930C23—C241.382 (3)
C6—C71.368 (3)C23—H230.930
C6—H60.930C24—C251.372 (3)
C7—C81.394 (3)C24—H240.930
C7—H70.930C25—C261.367 (3)
C8—C91.397 (2)C25—H250.930
C10—C111.514 (3)C26—C271.392 (3)
C10—H100.980C26—H260.930
C11—C121.387 (3)C27—H270.930
C18—N1—C10111.35 (14)O3—C14—C13125.1 (2)
C18—N1—H1124.3O3—C14—C15115.7 (2)
C10—N1—H1124.3C13—C14—C15119.2 (2)
C9—O2—C3113.97 (13)C16—C15—C14120.9 (2)
C14—O3—C17118.50 (19)C16—C15—H15119.6
C19—O5—C20116.5 (2)C14—C15—H15119.6
O1—C1—C8122.21 (15)C15—C16—C11121.4 (2)
O1—C1—C2122.82 (16)C15—C16—H16119.3
C8—C1—C2114.97 (14)C11—C16—H16119.3
C1—C2—C3106.62 (15)O3—C17—H17A109.5
C1—C2—C21114.60 (13)O3—C17—H17B109.5
C3—C2—C21111.58 (14)H17A—C17—H17B109.5
C1—C2—C10113.52 (14)O3—C17—H17C109.5
C3—C2—C10109.97 (14)H17A—C17—H17C109.5
C21—C2—C10100.56 (14)H17B—C17—H17C109.5
O2—C3—C2111.66 (15)N1—C18—C19110.35 (16)
O2—C3—H3A109.3N1—C18—C21103.59 (14)
C2—C3—H3A109.3C19—C18—C21112.89 (16)
O2—C3—H3B109.3N1—C18—H18109.9
C2—C3—H3B109.3C19—C18—H18109.9
H3A—C3—H3B107.9C21—C18—H18109.9
C5—C4—C9119.83 (17)O4—C19—O5123.9 (2)
C5—C4—H4120.1O4—C19—C18125.90 (19)
C9—C4—H4120.1O5—C19—C18110.22 (19)
C4—C5—C6120.05 (19)O5—C20—H20A109.5
C4—C5—H5120.0O5—C20—H20B109.5
C6—C5—H5120.0H20A—C20—H20B109.5
C7—C6—C5120.11 (17)O5—C20—H20C109.5
C7—C6—H6119.9H20A—C20—H20C109.5
C5—C6—H6119.9H20B—C20—H20C109.5
C6—C7—C8121.34 (17)C22—C21—C18115.78 (15)
C6—C7—H7119.3C22—C21—C2118.47 (15)
C8—C7—H7119.3C18—C21—C2101.17 (13)
C7—C8—C9117.41 (16)C22—C21—H21106.9
C7—C8—C1121.77 (15)C18—C21—H21106.9
C9—C8—C1120.75 (15)C2—C21—H21106.9
O2—C9—C4117.03 (15)C27—C22—C23117.80 (19)
O2—C9—C8121.81 (16)C27—C22—C21119.09 (17)
C4—C9—C8121.16 (16)C23—C22—C21123.09 (16)
N1—C10—C11112.75 (17)C24—C23—C22121.1 (2)
N1—C10—C2102.88 (14)C24—C23—H23119.4
C11—C10—C2114.37 (14)C22—C23—H23119.4
N1—C10—H10108.9C25—C24—C23120.3 (2)
C11—C10—H10108.9C25—C24—H24119.8
C2—C10—H10108.9C23—C24—H24119.8
C12—C11—C16116.8 (2)C26—C25—C24119.6 (2)
C12—C11—C10120.70 (18)C26—C25—H25120.2
C16—C11—C10122.50 (18)C24—C25—H25120.2
C13—C12—C11122.6 (2)C25—C26—C27120.6 (2)
C13—C12—H12118.7C25—C26—H26119.7
C11—C12—H12118.7C27—C26—H26119.7
C14—C13—C12119.2 (2)C22—C27—C26120.6 (2)
C14—C13—H13120.4C22—C27—H27119.7
C12—C13—H13120.4C26—C27—H27119.7
O1—C1—C2—C3146.52 (18)C11—C12—C13—C140.4 (3)
C8—C1—C2—C334.6 (2)C17—O3—C14—C130.2 (3)
O1—C1—C2—C2122.5 (3)C17—O3—C14—C15178.9 (2)
C8—C1—C2—C21158.57 (15)C12—C13—C14—O3179.1 (2)
O1—C1—C2—C1092.2 (2)C12—C13—C14—C150.1 (3)
C8—C1—C2—C1086.65 (18)O3—C14—C15—C16179.8 (2)
C9—O2—C3—C255.8 (2)C13—C14—C15—C160.6 (3)
C1—C2—C3—O261.75 (19)C14—C15—C16—C110.8 (3)
C21—C2—C3—O2172.43 (14)C12—C11—C16—C150.4 (3)
C10—C2—C3—O261.72 (19)C10—C11—C16—C15178.25 (19)
C9—C4—C5—C60.1 (3)C10—N1—C18—C19137.83 (18)
C4—C5—C6—C71.9 (3)C10—N1—C18—C2116.7 (2)
C5—C6—C7—C81.2 (3)C20—O5—C19—O42.7 (4)
C6—C7—C8—C91.4 (3)C20—O5—C19—C18176.6 (2)
C6—C7—C8—C1175.37 (18)N1—C18—C19—O480.5 (3)
O1—C1—C8—C75.1 (3)C21—C18—C19—O434.9 (3)
C2—C1—C8—C7173.82 (17)N1—C18—C19—O598.8 (2)
O1—C1—C8—C9178.24 (18)C21—C18—C19—O5145.81 (18)
C2—C1—C8—C92.9 (2)N1—C18—C21—C22167.61 (15)
C3—O2—C9—C4159.82 (18)C19—C18—C21—C2273.0 (2)
C3—O2—C9—C820.1 (3)N1—C18—C21—C238.19 (18)
C5—C4—C9—O2177.13 (18)C19—C18—C21—C2157.56 (16)
C5—C4—C9—C82.8 (3)C1—C2—C21—C2265.7 (2)
C7—C8—C9—O2176.51 (17)C3—C2—C21—C2255.6 (2)
C1—C8—C9—O26.7 (3)C10—C2—C21—C22172.19 (15)
C7—C8—C9—C43.4 (3)C1—C2—C21—C18166.62 (15)
C1—C8—C9—C4173.38 (18)C3—C2—C21—C1872.09 (19)
C18—N1—C10—C11112.19 (18)C10—C2—C21—C1844.49 (16)
C18—N1—C10—C211.5 (2)C18—C21—C22—C27137.40 (18)
C1—C2—C10—N1157.43 (15)C2—C21—C22—C27102.15 (19)
C3—C2—C10—N183.23 (18)C18—C21—C22—C2340.9 (2)
C21—C2—C10—N134.54 (17)C2—C21—C22—C2379.5 (2)
C1—C2—C10—C1134.8 (2)C27—C22—C23—C241.2 (3)
C3—C2—C10—C11154.15 (15)C21—C22—C23—C24179.51 (18)
C21—C2—C10—C1188.08 (17)C22—C23—C24—C250.7 (3)
N1—C10—C11—C12154.38 (17)C23—C24—C25—C260.0 (3)
C2—C10—C11—C1288.5 (2)C24—C25—C26—C270.3 (3)
N1—C10—C11—C1627.1 (2)C23—C22—C27—C260.9 (3)
C2—C10—C11—C1690.0 (2)C21—C22—C27—C26179.28 (18)
C16—C11—C12—C130.2 (3)C25—C26—C27—C220.1 (3)
C10—C11—C12—C13178.87 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3B···O1i0.972.483.432 (3)167
C7—H7···O2ii0.932.343.201 (3)153
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z.
 

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