Diethyl 7-oxo-3-(pyrrolidin-1-yl)­cyclo­octa-2,8-diene-1,2-di­carboxyl­ate

The title compound, C₁₈H₂₅NO₅, consists of a substituted 2,8-cyclo­octa­diene ring linked to a pyrrolidine ring through the N atom of the five-membered ring. The 2,8-cyclo­octa­diene moiety has a cis,cis configuration. The pyrrolidine ring adopts an envelope conformation. A few interatomic close contacts seem to influence the shape of the mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.117
• Data-to-parameter ratio = 9.9

checkCIF/PLATON results

No syntax errors found



Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           25.71
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               3124
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         3346
           Completeness (_total/calc)             93.37%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.93
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.85
PLAT157_ALERT_4_C Non-standard Monoclinic Beta Angle less 90 Deg        82.04 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.54 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.06 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Diethyl 7-oxo-3-(pyrrolidin-1-yl)cycloocta-2,8-diene-1,2-dicarboxylate

Crystal data

C18H25NO5	F(000) = 720
Mr = 335.39	Dx = 1.266 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 16.3870 (16) Å	θ = 11–22°
b = 9.5645 (12) Å	µ = 0.09 mm^−1
c = 11.3393 (19) Å	T = 293 K
β = 82.044 (10)°	Plate, yellow
V = 1760.1 (4) Å^3	0.40 × 0.25 × 0.10 mm
Z = 4

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.019
Radiation source: fine-focus sealed tube	θmax = 25.7°, θmin = 2.5°
Graphite monochromator	h = −20→20
non–profiled ω scans	k = 0→11
3194 measured reflections	l = −13→0
3124 independent reflections	3 standard reflections every 120 min
2047 reflections with I > 2σ(I)	intensity decay: 1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	All H-atom parameters refined
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0596P)^2 + 0.2352P] where P = (Fo^2 + 2Fc^2)/3
3124 reflections	(Δ/σ)max < 0.001
317 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

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
H41	0.0630 (11)	0.455 (2)	0.7470 (17)	0.038 (5)*
H42	0.1000 (10)	0.593 (2)	0.7969 (17)	0.035 (5)*
H181	0.1046 (14)	0.229 (3)	0.655 (2)	0.068 (7)*
H182	0.0622 (14)	0.338 (2)	0.577 (2)	0.061 (7)*
H152	0.2734 (12)	0.449 (2)	0.4668 (17)	0.043 (6)*
H132	0.4758 (13)	0.477 (2)	0.748 (2)	0.059 (7)*
H151	0.2920 (13)	0.298 (2)	0.5144 (19)	0.055 (6)*
H131	0.4902 (13)	0.457 (3)	0.608 (2)	0.063 (7)*
H102	0.4291 (15)	0.643 (3)	0.950 (2)	0.069 (8)*
H171	0.1753 (15)	0.115 (3)	0.499 (2)	0.069 (8)*
H172	0.0963 (15)	0.168 (3)	0.432 (2)	0.069 (7)*
H101	0.3551 (14)	0.699 (3)	1.042 (2)	0.061 (7)*
H141	0.5365 (16)	0.692 (3)	0.580 (3)	0.083 (9)*
H143	0.5163 (19)	0.711 (3)	0.726 (3)	0.102 (11)*
H51	0.0453 (13)	0.564 (3)	0.570 (2)	0.063 (7)*
H81	0.2073 (13)	0.886 (3)	0.798 (2)	0.056 (6)*
H52	0.0060 (13)	0.665 (2)	0.6726 (19)	0.057 (6)*
H162	0.1725 (16)	0.368 (3)	0.359 (2)	0.084 (9)*
H142	0.5888 (17)	0.614 (3)	0.667 (2)	0.079 (8)*
H161	0.2416 (17)	0.242 (3)	0.341 (2)	0.084 (8)*
H62	0.1633 (13)	0.703 (2)	0.5405 (17)	0.042 (6)*
H61	0.0841 (15)	0.799 (3)	0.529 (2)	0.072 (7)*
H113	0.314 (2)	0.469 (3)	1.096 (3)	0.098 (11)*
H112	0.3877 (18)	0.406 (4)	1.008 (3)	0.102 (11)*
H111	0.4085 (19)	0.500 (3)	1.120 (3)	0.107 (11)*
O3	0.34415 (8)	0.36473 (16)	0.67906 (13)	0.0469 (4)
O4	0.39487 (7)	0.58276 (14)	0.66305 (11)	0.0371 (3)
O2	0.31779 (8)	0.60687 (16)	0.90716 (12)	0.0460 (4)
C2	0.25154 (10)	0.5607 (2)	0.69375 (15)	0.0321 (4)
N1	0.18327 (9)	0.38448 (18)	0.59080 (13)	0.0365 (4)
C12	0.33222 (10)	0.4888 (2)	0.67724 (16)	0.0326 (4)
C3	0.18133 (10)	0.4898 (2)	0.66887 (15)	0.0328 (4)
C1	0.24907 (11)	0.6964 (2)	0.75342 (16)	0.0360 (5)
C13	0.47621 (11)	0.5262 (2)	0.6712 (2)	0.0426 (5)
O1	0.34500 (10)	0.82883 (18)	0.85184 (15)	0.0654 (5)
O5	0.09340 (11)	0.9465 (2)	0.70024 (19)	0.0810 (6)
C9	0.31047 (12)	0.7200 (2)	0.84020 (18)	0.0434 (5)
C8	0.19924 (13)	0.8081 (2)	0.74972 (19)	0.0459 (5)
C4	0.09685 (11)	0.5369 (3)	0.72362 (18)	0.0411 (5)
C15	0.24877 (13)	0.3596 (3)	0.49084 (18)	0.0449 (5)
C7	0.13349 (12)	0.8393 (2)	0.6786 (2)	0.0513 (6)
C14	0.53471 (15)	0.6465 (3)	0.6591 (3)	0.0610 (7)
C6	0.11407 (15)	0.7437 (3)	0.5819 (2)	0.0539 (6)
C5	0.05740 (13)	0.6250 (3)	0.6335 (2)	0.0515 (6)
C18	0.11464 (14)	0.2855 (3)	0.5846 (2)	0.0502 (6)
C10	0.37524 (17)	0.6200 (3)	0.9942 (2)	0.0573 (6)
C16	0.20273 (17)	0.2908 (3)	0.3993 (2)	0.0609 (7)
C11	0.3741 (3)	0.4873 (4)	1.0597 (3)	0.0816 (10)
C17	0.14275 (17)	0.1969 (3)	0.4762 (2)	0.0623 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0408 (7)	0.0347 (10)	0.0666 (10)	0.0033 (6)	−0.0130 (7)	0.0034 (7)
O4	0.0286 (6)	0.0385 (9)	0.0446 (8)	0.0001 (5)	−0.0068 (5)	0.0030 (6)
O2	0.0521 (8)	0.0503 (10)	0.0390 (8)	−0.0027 (7)	−0.0184 (6)	−0.0043 (7)
C2	0.0290 (9)	0.0349 (12)	0.0329 (10)	0.0012 (7)	−0.0056 (7)	0.0012 (8)
N1	0.0347 (8)	0.0427 (11)	0.0324 (9)	−0.0035 (7)	−0.0058 (6)	−0.0030 (7)
C12	0.0324 (9)	0.0354 (13)	0.0311 (10)	0.0004 (8)	−0.0080 (7)	0.0022 (8)
C3	0.0313 (9)	0.0402 (13)	0.0272 (10)	0.0014 (8)	−0.0057 (7)	0.0042 (8)
C1	0.0353 (9)	0.0405 (13)	0.0319 (11)	0.0009 (8)	−0.0034 (8)	−0.0015 (8)
C13	0.0291 (10)	0.0505 (15)	0.0489 (14)	0.0031 (9)	−0.0082 (9)	0.0013 (11)
O1	0.0762 (11)	0.0461 (12)	0.0793 (12)	−0.0086 (8)	−0.0305 (9)	−0.0095 (8)
O5	0.0634 (11)	0.0613 (14)	0.1207 (16)	0.0280 (9)	−0.0209 (10)	−0.0083 (11)
C9	0.0452 (11)	0.0396 (15)	0.0459 (13)	0.0025 (9)	−0.0082 (9)	−0.0089 (10)
C8	0.0465 (11)	0.0434 (15)	0.0474 (13)	0.0074 (10)	−0.0049 (10)	−0.0049 (10)
C4	0.0311 (10)	0.0567 (15)	0.0348 (12)	0.0006 (9)	−0.0018 (8)	−0.0030 (10)
C15	0.0471 (12)	0.0468 (16)	0.0393 (12)	0.0028 (11)	−0.0009 (10)	−0.0066 (10)
C7	0.0428 (11)	0.0495 (16)	0.0595 (14)	0.0097 (10)	0.0009 (10)	0.0080 (11)
C14	0.0377 (12)	0.070 (2)	0.0758 (19)	−0.0082 (12)	−0.0088 (12)	0.0050 (15)
C6	0.0492 (13)	0.0696 (18)	0.0439 (14)	0.0184 (12)	−0.0100 (11)	0.0113 (12)
C5	0.0368 (11)	0.0688 (17)	0.0506 (14)	0.0120 (11)	−0.0123 (10)	−0.0069 (12)
C18	0.0474 (13)	0.0518 (16)	0.0536 (15)	−0.0128 (11)	−0.0145 (11)	−0.0013 (11)
C10	0.0629 (15)	0.0668 (19)	0.0476 (14)	0.0035 (13)	−0.0265 (12)	−0.0139 (13)
C16	0.0735 (16)	0.062 (2)	0.0469 (15)	0.0028 (14)	−0.0082 (13)	−0.0162 (13)
C11	0.102 (3)	0.080 (3)	0.073 (2)	0.0066 (19)	−0.050 (2)	0.0007 (17)
C17	0.0681 (16)	0.0562 (19)	0.0668 (17)	−0.0054 (13)	−0.0236 (13)	−0.0161 (13)

Geometric parameters (Å, º)

O3—C12	1.204 (2)	C15—H152	0.97 (2)
O4—C12	1.357 (2)	C15—H151	0.99 (2)
O4—C13	1.453 (2)	C7—C6	1.495 (4)
O2—C9	1.337 (3)	C14—H141	0.99 (3)
O2—C10	1.461 (3)	C14—H143	1.00 (3)
C2—C3	1.398 (2)	C14—H142	0.96 (3)
C2—C1	1.462 (3)	C6—C5	1.530 (3)
C2—C12	1.479 (2)	C6—H62	0.96 (2)
N1—C3	1.338 (2)	C6—H61	0.99 (3)
N1—C15	1.468 (2)	C5—H51	0.97 (2)
N1—C18	1.479 (3)	C5—H52	0.98 (2)
C3—C4	1.506 (2)	C18—C17	1.511 (3)
C1—C8	1.348 (3)	C18—H181	0.95 (3)
C1—C9	1.518 (3)	C18—H182	1.01 (2)
C13—C14	1.492 (3)	C10—C11	1.469 (4)
C13—H132	0.99 (2)	C10—H102	0.98 (2)
C13—H131	0.98 (3)	C10—H101	0.96 (3)
O1—C9	1.201 (2)	C16—C17	1.515 (4)
O5—C7	1.224 (3)	C16—H162	1.03 (3)
C8—C7	1.464 (3)	C16—H161	0.97 (3)
C8—H81	0.95 (2)	C11—H113	1.03 (3)
C4—C5	1.535 (3)	C11—H112	0.98 (3)
C4—H41	0.97 (2)	C11—H111	0.95 (4)
C4—H42	1.00 (2)	C17—H171	1.00 (3)
C15—C16	1.516 (3)	C17—H172	1.00 (2)
C12—O4—C13	115.6 (2)	H141—C14—H143	113 (2)
C9—O2—C10	115.5 (2)	C13—C14—H142	109.5 (16)
C3—C2—C1	123.6 (2)	H141—C14—H142	109 (2)
C3—C2—C12	119.7 (2)	H143—C14—H142	108 (2)
C1—C2—C12	116.0 (2)	C7—C6—C5	110.7 (2)
C3—N1—C15	125.5 (2)	C7—C6—H62	110.8 (12)
C3—N1—C18	124.4 (2)	C5—C6—H62	108.4 (12)
C15—N1—C18	109.8 (2)	C7—C6—H61	106.9 (15)
O3—C12—O4	122.2 (2)	C5—C6—H61	107.9 (14)
O3—C12—C2	126.9 (2)	H62—C6—H61	112.1 (18)
O4—C12—C2	110.8 (2)	C6—C5—C4	111.9 (2)
N1—C3—C2	123.6 (2)	C6—C5—H51	109.8 (14)
N1—C3—C4	115.7 (2)	C4—C5—H51	108.3 (14)
C2—C3—C4	120.5 (2)	C6—C5—H52	108.7 (13)
C8—C1—C2	131.8 (2)	C4—C5—H52	109.3 (13)
C8—C1—C9	111.2 (2)	H51—C5—H52	108.8 (19)
C2—C1—C9	117.0 (2)	N1—C18—C17	104.4 (2)
O4—C13—C14	106.9 (2)	N1—C18—H181	111.4 (15)
O4—C13—H132	109.8 (12)	C17—C18—H181	111.0 (15)
C14—C13—H132	112.1 (13)	N1—C18—H182	110.4 (13)
O4—C13—H131	109.4 (13)	C17—C18—H182	112.1 (13)
C14—C13—H131	112.0 (14)	H181—C18—H182	107.5 (19)
H132—C13—H131	107 (2)	O2—C10—C11	107.7 (2)
O1—C9—O2	124.0 (2)	O2—C10—H102	106.9 (14)
O1—C9—C1	124.4 (2)	C11—C10—H102	113.7 (15)
O2—C9—C1	111.6 (2)	O2—C10—H101	104.2 (14)
C1—C8—C7	132.4 (2)	C11—C10—H101	114.7 (15)
C1—C8—H81	118.2 (14)	H102—C10—H101	109 (2)
C7—C8—H81	109.3 (14)	C17—C16—C15	102.0 (2)
C3—C4—C5	109.7 (2)	C17—C16—H162	111.5 (15)
C3—C4—H41	109.1 (11)	C15—C16—H162	108.0 (16)
C5—C4—H41	110.3 (11)	C17—C16—H161	114.7 (17)
C3—C4—H42	110.8 (10)	C15—C16—H161	109.6 (16)
C5—C4—H42	109.4 (11)	H162—C16—H161	111 (2)
H41—C4—H42	107.5 (15)	C10—C11—H113	107.1 (18)
N1—C15—C16	102.7 (2)	C10—C11—H112	113.2 (19)
N1—C15—H152	107.9 (12)	H113—C11—H112	104 (3)
C16—C15—H152	114.7 (12)	C10—C11—H111	106.8 (19)
N1—C15—H151	111.3 (13)	H113—C11—H111	111 (2)
C16—C15—H151	111.7 (13)	H112—C11—H111	115 (3)
H152—C15—H151	108.5 (17)	C18—C17—C16	103.7 (2)
O5—C7—C8	118.4 (2)	C18—C17—H171	110.2 (14)
O5—C7—C6	119.8 (2)	C16—C17—H171	106.6 (14)
C8—C7—C6	121.8 (2)	C18—C17—H172	113.0 (13)
C13—C14—H141	111.0 (16)	C16—C17—H172	110.7 (14)
C13—C14—H143	106.8 (18)	H171—C17—H172	112 (2)
C13—O4—C12—O3	−10.4 (3)	C2—C1—C9—O1	142.2 (2)
C13—O4—C12—C2	167.53 (16)	C8—C1—C9—O2	136.4 (2)
C3—C2—C12—O3	−24.4 (3)	C2—C1—C9—O2	−41.4 (2)
C1—C2—C12—O3	146.42 (19)	C2—C1—C8—C7	−5.3 (4)
C3—C2—C12—O4	157.8 (2)	C9—C1—C8—C7	177.2 (2)
C1—C2—C12—O4	−31.4 (2)	N1—C3—C4—C5	−76.3 (2)
C15—N1—C3—C2	−23.6 (3)	C2—C3—C4—C5	99.3 (2)
C18—N1—C3—C2	163.9 (2)	C3—N1—C15—C16	−149.4 (2)
C15—N1—C3—C4	151.9 (2)	C18—N1—C15—C16	24.0 (3)
C18—N1—C3—C4	−20.7 (3)	C1—C8—C7—O5	174.5 (2)
C1—C2—C3—N1	163.36 (17)	C1—C8—C7—C6	−5.0 (4)
C12—C2—C3—N1	−26.6 (3)	O5—C7—C6—C5	−96.3 (3)
C1—C2—C3—C4	−11.9 (3)	C8—C7—C6—C5	83.2 (3)
C12—C2—C3—C4	158.16 (17)	C7—C6—C5—C4	−59.9 (3)
C3—C2—C1—C8	−34.7 (3)	C3—C4—C5—C6	−52.2 (3)
C12—C2—C1—C8	154.9 (2)	C3—N1—C18—C17	174.5 (2)
C3—C2—C1—C9	142.61 (18)	C15—N1—C18—C17	1.0 (3)
C12—C2—C1—C9	−27.8 (2)	C9—O2—C10—C11	179.3 (2)
C12—O4—C13—C14	−177.33 (19)	N1—C15—C16—C17	−39.1 (3)
C10—O2—C9—O1	−3.2 (3)	N1—C18—C17—C16	−25.7 (3)
C10—O2—C9—C1	−179.56 (17)	C15—C16—C17—C18	40.3 (3)
C8—C1—C9—O1	−39.9 (3)