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The title compound, C27H24N2O4, has been synthesized as a potential pharmacologically active compound. All bond lengths and angles are within normal ranges and the mol­ecules are linked into centrosymmetric R22(14) dimers by a simple N—H...O inter­action. The packing is stabilized through inter­molecular N—H...O hydrogen bonds and van der Waals inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038755/bx2097sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038755/bx2097Isup2.hkl
Contains datablock I

CCDC reference: 660279

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.043
  • wR factor = 0.115
  • Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C1 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C2 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C3 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL008_ALERT_1_A _publ_section_title is missing. Title of paper.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Comment top

Spiroheterocycles represent an important class of naturally occurring substances characterized by their highly pronounced biological activities·(James et al., 1991) Highly substituted pyrrolidines have gained much prominence since they form the central skeleton of many natural products and pharmacologically active compounds. (Deshong & Leginus, 1983). Pyrrolidine and oxindole alkaloids (Fujimori, 1990) constitute another class of compounds with significant biological activity which are normally found in rhyncophylline, corynoxeine, nitraphylline, vincatine, horsifiline,etc (Henrickson & Silva, 1962).

In the crystal structure of the title compound, C27H24N2O4, the chromanone moiety consists of a methoxy benzene ring fused with a six membered heterocyclic ring which adopts a sofa conformation (Abdul Ajees et al., 2001). The five membered spiropyrrolidine ring is in an envelope conformation. The oxindole and phenyl rings attached to the five membered rings are nearly perpendicular to each other. The molecules are linked into centrosymmetric R22(14) dimmer by a simple N—H···O interaction (Bernstein et al., 1995)

Related literature top

For related literature, see: Abdul Ajees et al. (2001); Bernstein et al. (1995); Deshong & Leginus (1983); Fujimori (1990); Henrickson & Silva (1962); James et al. (1991).

Experimental top

A mixture of Isatin (1H-indole-2,3-dione) (1 mmol, 0.082 g), Sarcosine (2-methylaminoacetic acid) (1 mmol, 0.046 g) and the dipolarophile (3-arylidene-4-chromanone) (1 mmol, 0.2 g) in aqueous methanol (20 ml) was refluxed for 5 h and was subsequently monitored by TLC for the disappearance of starting materials. The solvent was removed under reduced pressure and the crude product was purified by column chromatography using silica gel and hexane–ethyl acetate (5:1) as eluent to give the cycloadduct.

Refinement top

All the H atoms were geometrically fixed at chemically meaningful positions. The hydrogen atoms of the phenyl ring were allowed to ride at a distance of 0.93 Å from the parent carbons and their thermal parameter were fixed at 1.2 times that of the parent atom.

The secondary CH2 H atoms were fixed at a distance of 0.97 Å from the parent atom and their thermal parameters were fixed at 1.2 times the parent atom.

The CH3 H atoms attached to Nitrogen were fixed at a distance of 0.96 Å from the parent atom and their thermal parameters were fixed at 1.5 times the parent atom. similarly the CH3 H atoms attached to Oxygen were fixed at a distance of 0.96 Å from the parent atom and their thermal parameters were fixed at 1.5 times the parent atom.

Structure description top

Spiroheterocycles represent an important class of naturally occurring substances characterized by their highly pronounced biological activities·(James et al., 1991) Highly substituted pyrrolidines have gained much prominence since they form the central skeleton of many natural products and pharmacologically active compounds. (Deshong & Leginus, 1983). Pyrrolidine and oxindole alkaloids (Fujimori, 1990) constitute another class of compounds with significant biological activity which are normally found in rhyncophylline, corynoxeine, nitraphylline, vincatine, horsifiline,etc (Henrickson & Silva, 1962).

In the crystal structure of the title compound, C27H24N2O4, the chromanone moiety consists of a methoxy benzene ring fused with a six membered heterocyclic ring which adopts a sofa conformation (Abdul Ajees et al., 2001). The five membered spiropyrrolidine ring is in an envelope conformation. The oxindole and phenyl rings attached to the five membered rings are nearly perpendicular to each other. The molecules are linked into centrosymmetric R22(14) dimmer by a simple N—H···O interaction (Bernstein et al., 1995)

For related literature, see: Abdul Ajees et al. (2001); Bernstein et al. (1995); Deshong & Leginus (1983); Fujimori (1990); Henrickson & Silva (1962); James et al. (1991).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. ORTEP representation of the molecule showing the atom numbering scheme. Thermal ellipsoids are drawn with 30% probability.
[Figure 2] Fig. 2. Packing diagram of title compound projected down the C-axis
6-Methoxy-1'-methyl-4'-phenylchroman-3-spiro-3'-pyrrolidine-2'-spiro-3''(2''H)- indole-2'',4-dione top
Crystal data top
C27H24N2O4F(000) = 928
Mr = 440.48Dx = 1.334 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8137 reflections
a = 9.2244 (2) Åθ = 2.4–26.8°
b = 26.1163 (5) ŵ = 0.09 mm1
c = 9.3506 (2) ÅT = 295 K
β = 103.233 (1)°Rectangular, colourless
V = 2192.81 (8) Å30.23 × 0.21 × 0.15 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
5379 independent reflections
Radiation source: fine-focus sealed tube3670 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 28.4°, θmin = 1.6°
Absorption correction: multi-scan
(Blessing, 1995)
h = 1112
Tmin = 0.899, Tmax = 0.987k = 3434
27791 measured reflectionsl = 1210
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0481P)2 + 0.486P]
where P = (Fo2 + 2Fc2)/3
5379 reflections(Δ/σ)max < 0.001
304 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C27H24N2O4V = 2192.81 (8) Å3
Mr = 440.48Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.2244 (2) ŵ = 0.09 mm1
b = 26.1163 (5) ÅT = 295 K
c = 9.3506 (2) Å0.23 × 0.21 × 0.15 mm
β = 103.233 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
5379 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)
3670 reflections with I > 2σ(I)
Tmin = 0.899, Tmax = 0.987Rint = 0.032
27791 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.24 e Å3
5379 reflectionsΔρmin = 0.18 e Å3
304 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.

The reflections with Bragg angle less than 2.4° could not be collected due to the hinderence of the beam stop. This lead to the absence of 14 low angle reflections from the measured data. As b axis length is quite large (26.116 Å) for the wave length used (0.71073 Å),it became unavoidable. Except for these missing low angle reflections, the data set is complete with in 50° two theta.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.25225 (16)0.09504 (5)0.02539 (14)0.0343 (3)
C20.34793 (15)0.14452 (5)0.00669 (13)0.0312 (3)
C30.23382 (16)0.17999 (5)0.09708 (14)0.0338 (3)
H30.19200.20250.03300.041*
C40.11035 (18)0.14375 (6)0.16772 (16)0.0445 (4)
H4A0.01780.16190.20580.053*
H4B0.13670.12420.24630.053*
C50.30377 (17)0.04717 (5)0.05042 (16)0.0401 (3)
C60.31749 (17)0.02527 (5)0.18915 (16)0.0392 (3)
C70.3394 (2)0.00243 (6)0.31793 (19)0.0552 (4)
H70.37710.03560.32370.066*
C80.3033 (2)0.02077 (7)0.43793 (19)0.0640 (5)
H80.31830.00310.52640.077*
C90.2459 (2)0.06933 (8)0.4293 (2)0.0639 (5)
H90.22100.08400.51110.077*
C100.2246 (2)0.09686 (7)0.29919 (18)0.0512 (4)
H100.18480.12970.29320.061*
C110.26312 (16)0.07498 (5)0.17921 (15)0.0366 (3)
C120.40941 (16)0.16912 (5)0.15696 (14)0.0343 (3)
C130.48437 (16)0.13335 (5)0.05463 (15)0.0364 (3)
H13A0.45200.11990.15350.044*
H13B0.53750.16510.06010.044*
C140.74957 (18)0.08581 (6)0.26498 (18)0.0462 (4)
H140.80210.06200.22270.055*
C150.79350 (18)0.09709 (6)0.41191 (19)0.0514 (4)
H150.87570.08050.46930.062*
C160.71684 (18)0.13301 (6)0.47627 (16)0.0452 (4)
C170.59566 (17)0.15788 (6)0.39204 (15)0.0403 (3)
H170.54520.18240.43420.048*
C180.54837 (16)0.14622 (5)0.24221 (15)0.0348 (3)
C190.62592 (16)0.11033 (5)0.18011 (15)0.0369 (3)
C200.6949 (2)0.17725 (8)0.69199 (18)0.0620 (5)
H20A0.70260.21040.64970.093*
H20B0.73930.17830.79540.093*
H20C0.59180.16790.67720.093*
C210.29494 (16)0.21463 (5)0.19882 (15)0.0356 (3)
C220.38359 (19)0.25574 (6)0.14124 (19)0.0512 (4)
H220.40760.26080.04010.061*
C230.4371 (2)0.28933 (7)0.2299 (2)0.0655 (5)
H230.49680.31660.18820.079*
C240.4031 (2)0.28291 (7)0.3794 (2)0.0645 (5)
H240.43970.30560.43930.077*
C250.3146 (2)0.24280 (8)0.4395 (2)0.0660 (5)
H250.29050.23820.54080.079*
C260.2605 (2)0.20884 (6)0.34931 (17)0.0523 (4)
H260.20000.18180.39140.063*
C270.0093 (2)0.06977 (7)0.0786 (2)0.0661 (5)
H27A0.10680.08410.11360.099*
H27B0.00730.04990.00810.099*
H27C0.01450.04820.15320.099*
N10.10004 (14)0.11104 (5)0.04404 (14)0.0428 (3)
N20.33944 (15)0.00992 (5)0.05262 (14)0.0447 (3)
O10.30669 (15)0.04317 (4)0.17904 (12)0.0583 (3)
O20.34710 (13)0.20420 (4)0.20365 (11)0.0502 (3)
O30.58380 (11)0.09720 (4)0.03378 (10)0.0406 (2)
O40.76976 (14)0.14063 (5)0.62380 (12)0.0631 (4)
H20.369 (2)0.0207 (7)0.0335 (18)0.056 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0353 (8)0.0335 (7)0.0331 (7)0.0026 (6)0.0057 (6)0.0026 (5)
C20.0316 (7)0.0319 (7)0.0283 (6)0.0027 (5)0.0034 (5)0.0017 (5)
C30.0340 (8)0.0341 (7)0.0312 (7)0.0030 (6)0.0031 (6)0.0031 (5)
C40.0405 (9)0.0435 (8)0.0434 (8)0.0033 (7)0.0028 (7)0.0106 (6)
C50.0416 (9)0.0377 (8)0.0408 (8)0.0044 (6)0.0089 (6)0.0043 (6)
C60.0375 (8)0.0360 (7)0.0423 (8)0.0003 (6)0.0052 (6)0.0051 (6)
C70.0607 (12)0.0438 (9)0.0566 (10)0.0029 (8)0.0042 (8)0.0178 (8)
C80.0752 (14)0.0695 (12)0.0444 (9)0.0103 (10)0.0080 (9)0.0191 (9)
C90.0805 (14)0.0718 (13)0.0456 (10)0.0028 (10)0.0274 (9)0.0062 (9)
C100.0603 (11)0.0508 (9)0.0486 (9)0.0088 (8)0.0251 (8)0.0042 (7)
C110.0359 (8)0.0366 (7)0.0377 (7)0.0028 (6)0.0088 (6)0.0067 (6)
C120.0360 (8)0.0350 (7)0.0309 (7)0.0034 (6)0.0059 (6)0.0001 (5)
C130.0372 (8)0.0371 (7)0.0342 (7)0.0035 (6)0.0068 (6)0.0017 (6)
C140.0381 (9)0.0403 (8)0.0555 (9)0.0088 (7)0.0010 (7)0.0036 (7)
C150.0391 (9)0.0468 (9)0.0577 (10)0.0070 (7)0.0110 (7)0.0040 (7)
C160.0424 (9)0.0450 (8)0.0400 (8)0.0017 (7)0.0076 (7)0.0000 (6)
C170.0397 (9)0.0397 (8)0.0373 (7)0.0019 (6)0.0001 (6)0.0027 (6)
C180.0324 (8)0.0347 (7)0.0343 (7)0.0009 (6)0.0017 (6)0.0001 (5)
C190.0325 (8)0.0356 (7)0.0395 (7)0.0003 (6)0.0020 (6)0.0011 (6)
C200.0552 (12)0.0884 (14)0.0374 (9)0.0034 (10)0.0002 (8)0.0058 (9)
C210.0361 (8)0.0329 (7)0.0364 (7)0.0063 (6)0.0056 (6)0.0056 (5)
C220.0531 (11)0.0486 (9)0.0514 (9)0.0090 (8)0.0108 (8)0.0020 (7)
C230.0593 (12)0.0541 (11)0.0840 (14)0.0137 (9)0.0184 (10)0.0117 (10)
C240.0611 (12)0.0623 (12)0.0771 (13)0.0105 (10)0.0303 (10)0.0346 (10)
C250.0859 (15)0.0689 (12)0.0454 (10)0.0115 (11)0.0198 (9)0.0215 (9)
C260.0691 (12)0.0464 (9)0.0386 (8)0.0006 (8)0.0066 (8)0.0062 (7)
C270.0445 (11)0.0580 (11)0.0868 (14)0.0137 (8)0.0037 (9)0.0233 (10)
N10.0331 (7)0.0415 (7)0.0501 (7)0.0029 (5)0.0016 (5)0.0129 (5)
N20.0542 (9)0.0291 (6)0.0512 (8)0.0048 (6)0.0128 (6)0.0010 (6)
O10.0835 (9)0.0523 (7)0.0413 (6)0.0062 (6)0.0193 (6)0.0107 (5)
O20.0557 (7)0.0523 (6)0.0382 (6)0.0214 (5)0.0016 (5)0.0078 (5)
O30.0389 (6)0.0404 (5)0.0406 (5)0.0098 (4)0.0053 (4)0.0045 (4)
O40.0609 (8)0.0731 (8)0.0417 (6)0.0111 (6)0.0166 (6)0.0063 (6)
Geometric parameters (Å, º) top
C1—N11.4663 (18)C14—C151.372 (2)
C1—C111.5124 (18)C14—C191.388 (2)
C1—C51.5638 (19)C14—H140.9300
C1—C21.5970 (19)C15—C161.392 (2)
C2—C131.5258 (19)C15—H150.9300
C2—C121.5309 (18)C16—O41.3685 (18)
C2—C31.5620 (18)C16—C171.374 (2)
C3—C41.511 (2)C17—C181.4022 (19)
C3—C211.5123 (19)C17—H170.9300
C3—H30.9800C18—C191.3847 (19)
C4—N11.4583 (18)C19—O31.3774 (16)
C4—H4A0.9700C20—O41.414 (2)
C4—H4B0.9700C20—H20A0.9600
C5—O11.2136 (17)C20—H20B0.9600
C5—N21.3558 (19)C20—H20C0.9600
C6—C71.379 (2)C21—C261.378 (2)
C6—C111.387 (2)C21—C221.382 (2)
C6—N21.3964 (19)C22—C231.374 (2)
C7—C81.381 (3)C22—H220.9300
C7—H70.9300C23—C241.371 (3)
C8—C91.369 (3)C23—H230.9300
C8—H80.9300C24—C251.367 (3)
C9—C101.388 (2)C24—H240.9300
C9—H90.9300C25—C261.393 (2)
C10—C111.376 (2)C25—H250.9300
C10—H100.9300C26—H260.9300
C12—O21.2147 (16)C27—N11.461 (2)
C12—C181.4726 (19)C27—H27A0.9600
C13—O31.4384 (16)C27—H27B0.9600
C13—H13A0.9700C27—H27C0.9600
C13—H13B0.9700N2—H20.878 (18)
N1—C1—C11111.60 (11)C15—C14—H14120.4
N1—C1—C5112.75 (11)C19—C14—H14120.4
C11—C1—C5101.15 (11)C14—C15—C16120.98 (14)
N1—C1—C2102.60 (10)C14—C15—H15119.5
C11—C1—C2117.80 (11)C16—C15—H15119.5
C5—C1—C2111.37 (11)O4—C16—C17124.37 (15)
C13—C2—C12105.13 (11)O4—C16—C15115.76 (14)
C13—C2—C3112.11 (11)C17—C16—C15119.86 (14)
C12—C2—C3112.14 (11)C16—C17—C18119.74 (14)
C13—C2—C1114.24 (11)C16—C17—H17120.1
C12—C2—C1109.69 (10)C18—C17—H17120.1
C3—C2—C1103.71 (10)C19—C18—C17119.58 (13)
C4—C3—C21116.86 (11)C19—C18—C12121.14 (12)
C4—C3—C2103.50 (11)C17—C18—C12119.06 (12)
C21—C3—C2116.76 (11)O3—C19—C18121.99 (12)
C4—C3—H3106.3O3—C19—C14117.46 (13)
C21—C3—H3106.3C18—C19—C14120.55 (13)
C2—C3—H3106.3O4—C20—H20A109.5
N1—C4—C3101.52 (11)O4—C20—H20B109.5
N1—C4—H4A111.5H20A—C20—H20B109.5
C3—C4—H4A111.5O4—C20—H20C109.5
N1—C4—H4B111.5H20A—C20—H20C109.5
C3—C4—H4B111.5H20B—C20—H20C109.5
H4A—C4—H4B109.3C26—C21—C22117.43 (14)
O1—C5—N2125.84 (14)C26—C21—C3123.00 (13)
O1—C5—C1126.59 (13)C22—C21—C3119.50 (13)
N2—C5—C1107.52 (12)C23—C22—C21121.54 (17)
C7—C6—C11121.86 (14)C23—C22—H22119.2
C7—C6—N2128.65 (14)C21—C22—H22119.2
C11—C6—N2109.47 (12)C24—C23—C22120.48 (18)
C6—C7—C8117.69 (16)C24—C23—H23119.8
C6—C7—H7121.2C22—C23—H23119.8
C8—C7—H7121.2C25—C24—C23119.24 (16)
C9—C8—C7121.33 (16)C25—C24—H24120.4
C9—C8—H8119.3C23—C24—H24120.4
C7—C8—H8119.3C24—C25—C26120.14 (17)
C8—C9—C10120.46 (17)C24—C25—H25119.9
C8—C9—H9119.8C26—C25—H25119.9
C10—C9—H9119.8C21—C26—C25121.17 (16)
C11—C10—C9119.22 (16)C21—C26—H26119.4
C11—C10—H10120.4C25—C26—H26119.4
C9—C10—H10120.4N1—C27—H27A109.5
C10—C11—C6119.40 (13)N1—C27—H27B109.5
C10—C11—C1131.16 (13)H27A—C27—H27B109.5
C6—C11—C1109.40 (12)N1—C27—H27C109.5
O2—C12—C18122.46 (12)H27A—C27—H27C109.5
O2—C12—C2122.69 (12)H27B—C27—H27C109.5
C18—C12—C2114.84 (11)C4—N1—C27115.06 (13)
O3—C13—C2112.44 (11)C4—N1—C1106.76 (11)
O3—C13—H13A109.1C27—N1—C1115.48 (12)
C2—C13—H13A109.1C5—N2—C6112.41 (12)
O3—C13—H13B109.1C5—N2—H2123.1 (11)
C2—C13—H13B109.1C6—N2—H2124.4 (11)
H13A—C13—H13B107.8C19—O3—C13113.90 (10)
C15—C14—C19119.28 (14)C16—O4—C20117.03 (13)
N1—C1—C2—C13131.28 (11)C1—C2—C13—O357.31 (15)
C11—C1—C2—C13105.74 (13)C19—C14—C15—C160.6 (3)
C5—C1—C2—C1310.42 (15)C14—C15—C16—O4179.25 (15)
N1—C1—C2—C12111.00 (12)C14—C15—C16—C170.3 (3)
C11—C1—C2—C1211.98 (16)O4—C16—C17—C18178.35 (15)
C5—C1—C2—C12128.14 (12)C15—C16—C17—C181.2 (2)
N1—C1—C2—C38.95 (13)C16—C17—C18—C191.1 (2)
C11—C1—C2—C3131.93 (12)C16—C17—C18—C12173.62 (14)
C5—C1—C2—C3111.90 (12)O2—C12—C18—C19172.56 (14)
C13—C2—C3—C4104.93 (13)C2—C12—C18—C198.73 (19)
C12—C2—C3—C4137.07 (12)O2—C12—C18—C1712.8 (2)
C1—C2—C3—C418.80 (13)C2—C12—C18—C17165.90 (12)
C13—C2—C3—C2124.98 (16)C17—C18—C19—O3179.60 (13)
C12—C2—C3—C2193.02 (14)C12—C18—C19—O35.0 (2)
C1—C2—C3—C21148.71 (11)C17—C18—C19—C140.2 (2)
C21—C3—C4—N1169.87 (12)C12—C18—C19—C14174.45 (14)
C2—C3—C4—N140.03 (14)C15—C14—C19—O3178.76 (14)
N1—C1—C5—O156.5 (2)C15—C14—C19—C180.7 (2)
C11—C1—C5—O1175.82 (15)C4—C3—C21—C2610.6 (2)
C2—C1—C5—O158.19 (19)C2—C3—C21—C26112.71 (16)
N1—C1—C5—N2121.14 (13)C4—C3—C21—C22166.10 (14)
C11—C1—C5—N21.84 (15)C2—C3—C21—C2270.64 (17)
C2—C1—C5—N2124.15 (12)C26—C21—C22—C230.7 (2)
C11—C6—C7—C80.8 (3)C3—C21—C22—C23177.56 (16)
N2—C6—C7—C8177.26 (16)C21—C22—C23—C240.2 (3)
C6—C7—C8—C90.9 (3)C22—C23—C24—C250.3 (3)
C7—C8—C9—C101.0 (3)C23—C24—C25—C260.3 (3)
C8—C9—C10—C110.6 (3)C22—C21—C26—C250.8 (2)
C9—C10—C11—C62.2 (2)C3—C21—C26—C25177.49 (15)
C9—C10—C11—C1179.56 (16)C24—C25—C26—C210.3 (3)
C7—C6—C11—C102.4 (2)C3—C4—N1—C27178.03 (14)
N2—C6—C11—C10176.04 (14)C3—C4—N1—C148.48 (14)
C7—C6—C11—C1179.73 (14)C11—C1—N1—C4162.45 (12)
N2—C6—C11—C11.85 (17)C5—C1—N1—C484.51 (14)
N1—C1—C11—C1055.2 (2)C2—C1—N1—C435.40 (14)
C5—C1—C11—C10175.36 (16)C11—C1—N1—C2768.24 (17)
C2—C1—C11—C1063.1 (2)C5—C1—N1—C2744.80 (18)
N1—C1—C11—C6122.33 (13)C2—C1—N1—C27164.71 (13)
C5—C1—C11—C62.20 (15)O1—C5—N2—C6176.80 (15)
C2—C1—C11—C6119.38 (13)C1—C5—N2—C60.88 (17)
C13—C2—C12—O2141.65 (14)C7—C6—N2—C5178.87 (16)
C3—C2—C12—O219.57 (19)C11—C6—N2—C50.59 (18)
C1—C2—C12—O295.10 (16)C18—C19—O3—C1317.24 (19)
C13—C2—C12—C1839.64 (15)C14—C19—O3—C13163.30 (13)
C3—C2—C12—C18161.72 (12)C2—C13—O3—C1953.20 (15)
C1—C2—C12—C1883.61 (14)C17—C16—O4—C201.0 (2)
C12—C2—C13—O362.99 (13)C15—C16—O4—C20179.47 (15)
C3—C2—C13—O3174.93 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.878 (18)2.167 (19)3.0401 (16)172.8 (16)
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC27H24N2O4
Mr440.48
Crystal system, space groupMonoclinic, P21/n
Temperature (K)295
a, b, c (Å)9.2244 (2), 26.1163 (5), 9.3506 (2)
β (°) 103.233 (1)
V3)2192.81 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.23 × 0.21 × 0.15
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(Blessing, 1995)
Tmin, Tmax0.899, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
27791, 5379, 3670
Rint0.032
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.115, 1.02
No. of reflections5379
No. of parameters304
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.24, 0.18

Computer programs: APEX2 (Bruker, 2004), APEX2, SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.878 (18)2.167 (19)3.0401 (16)172.8 (16)
Symmetry code: (i) x+1, y, z.
 

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