Succinimido 4-(N-maleimido­methyl)­cyclo­hexane­carboxyl­ate

The title compound {alternative name: 2,5-dioxo-3-pyrrolidin-1-yl 4-[(2,5-dioxo-3-pyrrolin-1-yl)­methyl]­cyclo­hexane­car­box­yl­ate}, C₁₆H₁₈N₂O₆, crystallizes as discrete mol­ecules separated by normal van der Waals interactions. The succin­imide ester and male­imide subunits occupy equatorial positions on the cyclo­hexane ring.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.132
• Data-to-parameter ratio = 17.6

checkCIF/PLATON results

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Alert level C
PLAT432_ALERT_2_C Short Inter X...Y Contact  O6     ..  C1      ..       2.93 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: MSC/AFC7 Diffractometer Control Software for Windows (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control Software for Windows; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 2001); program(s) used to solve structure: TEXSAN for Windows; program(s) used to refine structure: TEXSAN for Windows and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows and PLATON (Spek, 2003).

2,5-dioxo-3-pyrrolidin-1-yl 4-[(2,5-dioxo-3-pyrrolin-1-yl)methyl]cyclohexanecarboxylate

Crystal data

C16H18N2O6	F(000) = 1408
Mr = 334.32	Dx = 1.339 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 20.203 (5) Å	θ = 12.7–17.3°
b = 17.021 (6) Å	µ = 0.10 mm^−1
c = 9.643 (3) Å	T = 295 K
V = 3316.0 (18) Å^3	Prismatic, colorless
Z = 8	0.50 × 0.30 × 0.30 mm

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.032
Radiation source: Rigaku rotating anode	θmax = 27.5°, θmin = 2.6°
Graphite monochromator	h = 0→26
ω scans	k = −10→22
4776 measured reflections	l = −5→12
3816 independent reflections	3 standard reflections every 150 reflections
1926 reflections with I > 2σ(I)	intensity decay: 0.1%

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0582P)^2] where P = (Fo^2 + 2Fc^2)/3
3816 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

Experimental. The scan width was (1.16 + 0.30tanθ)° with an ω scan speed of 16° per minute (up to 4 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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
O1	1.01335 (8)	0.12423 (9)	0.71523 (18)	0.0763 (6)
O2	1.13009 (8)	0.35109 (8)	0.75828 (17)	0.0719 (6)
O3	1.01468 (6)	0.27223 (8)	0.83813 (14)	0.0535 (5)
O4	0.96263 (8)	0.31438 (11)	0.64521 (16)	0.0890 (7)
O5	0.70698 (8)	0.61940 (9)	0.91231 (19)	0.0821 (7)
O6	0.65424 (7)	0.38235 (9)	1.09544 (17)	0.0723 (6)
N1	1.06275 (7)	0.24343 (9)	0.74894 (18)	0.0478 (5)
N2	0.69835 (7)	0.49801 (9)	1.01501 (17)	0.0473 (5)
C1	1.05851 (10)	0.16876 (12)	0.6942 (2)	0.0494 (7)
C2	1.11881 (10)	0.15878 (11)	0.6077 (2)	0.0512 (7)
C3	1.15952 (10)	0.23267 (12)	0.6275 (2)	0.0584 (8)
C4	1.11900 (9)	0.28542 (12)	0.7176 (2)	0.0476 (7)
C5	0.96279 (10)	0.30890 (12)	0.7679 (2)	0.0531 (7)
C6	0.91403 (9)	0.33876 (12)	0.8710 (2)	0.0469 (6)
C7	0.93364 (8)	0.42123 (12)	0.9170 (2)	0.0528 (7)
C8	0.88372 (9)	0.45344 (11)	1.0203 (2)	0.0515 (7)
C9	0.81396 (8)	0.45481 (11)	0.96089 (18)	0.0422 (6)
C10	0.79422 (9)	0.37305 (11)	0.9124 (2)	0.0493 (6)
C11	0.84403 (10)	0.33872 (12)	0.8104 (2)	0.0554 (7)
C12	0.76603 (9)	0.48919 (11)	1.0666 (2)	0.0521 (7)
C13	0.67435 (11)	0.56317 (13)	0.9443 (2)	0.0550 (7)
C14	0.60298 (10)	0.54691 (14)	0.9182 (2)	0.0643 (8)
C15	0.58844 (10)	0.47784 (14)	0.9681 (3)	0.0652 (9)
C16	0.64840 (9)	0.44385 (13)	1.0346 (2)	0.0524 (7)
H2A	1.10700	0.15230	0.51310	0.0570*
H2B	1.14310	0.11390	0.63790	0.0570*
H3A	1.16780	0.25680	0.53990	0.0660*
H3B	1.20060	0.22050	0.67040	0.0660*
H6	0.91490	0.30480	0.94920	0.0520*
H7A	0.93490	0.45480	0.83800	0.0590*
H7B	0.97630	0.41940	0.95820	0.0590*
H8A	0.88440	0.42070	1.10110	0.0590*
H8B	0.89640	0.50510	1.04580	0.0590*
H9	0.81410	0.48810	0.88170	0.0480*
H10A	0.79180	0.33910	0.99090	0.0560*
H10B	0.75230	0.37540	0.86870	0.0560*
H11A	0.84390	0.36930	0.72800	0.0610*
H11B	0.83200	0.28610	0.78890	0.0610*
H12A	0.76470	0.45500	1.14490	0.0590*
H12B	0.78170	0.53900	1.09400	0.0590*
H14	0.57280	0.58070	0.87200	0.0740*
H15	0.54590	0.45340	0.96460	0.0730*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0627 (10)	0.0780 (11)	0.0882 (12)	−0.0282 (8)	0.0077 (9)	−0.0039 (9)
O2	0.0824 (11)	0.0539 (9)	0.0793 (11)	−0.0131 (8)	0.0183 (9)	−0.0151 (9)
O3	0.0379 (7)	0.0711 (9)	0.0515 (8)	0.0163 (6)	0.0061 (6)	0.0025 (7)
O4	0.0773 (12)	0.1376 (16)	0.0520 (10)	0.0493 (11)	0.0069 (9)	0.0060 (10)
O5	0.0715 (11)	0.0660 (11)	0.1087 (14)	0.0052 (9)	0.0171 (10)	0.0226 (10)
O6	0.0672 (10)	0.0668 (10)	0.0829 (12)	0.0049 (8)	0.0221 (9)	0.0184 (9)
N1	0.0350 (8)	0.0486 (9)	0.0599 (10)	0.0074 (7)	0.0097 (8)	−0.0019 (8)
N2	0.0344 (8)	0.0522 (9)	0.0552 (10)	0.0074 (7)	0.0051 (8)	0.0030 (8)
C1	0.0432 (11)	0.0526 (12)	0.0525 (12)	−0.0026 (10)	−0.0040 (10)	0.0038 (10)
C2	0.0540 (12)	0.0477 (11)	0.0520 (12)	0.0048 (10)	0.0030 (10)	0.0007 (9)
C3	0.0456 (12)	0.0566 (13)	0.0731 (15)	0.0032 (10)	0.0184 (11)	−0.0007 (11)
C4	0.0418 (11)	0.0495 (11)	0.0515 (12)	−0.0002 (9)	0.0051 (9)	0.0015 (9)
C5	0.0419 (11)	0.0624 (13)	0.0550 (13)	0.0115 (10)	0.0020 (10)	0.0040 (11)
C6	0.0381 (10)	0.0546 (12)	0.0481 (11)	0.0102 (9)	0.0036 (9)	0.0039 (9)
C7	0.0300 (9)	0.0639 (13)	0.0646 (13)	0.0032 (9)	−0.0048 (9)	0.0012 (11)
C8	0.0359 (10)	0.0561 (12)	0.0625 (13)	0.0055 (9)	−0.0101 (10)	−0.0074 (10)
C9	0.0319 (9)	0.0461 (11)	0.0487 (11)	0.0038 (8)	−0.0039 (8)	0.0024 (9)
C10	0.0327 (9)	0.0523 (11)	0.0629 (13)	−0.0013 (8)	0.0000 (10)	−0.0043 (10)
C11	0.0412 (11)	0.0580 (13)	0.0670 (14)	0.0023 (10)	0.0016 (10)	−0.0146 (10)
C12	0.0412 (11)	0.0588 (13)	0.0564 (12)	0.0065 (9)	−0.0043 (9)	−0.0050 (10)
C13	0.0490 (12)	0.0594 (13)	0.0565 (13)	0.0121 (10)	0.0121 (10)	0.0019 (11)
C14	0.0446 (12)	0.0833 (17)	0.0649 (14)	0.0238 (12)	−0.0006 (11)	0.0021 (13)
C15	0.0334 (10)	0.0819 (17)	0.0803 (17)	0.0068 (11)	0.0085 (11)	−0.0092 (14)
C16	0.0422 (11)	0.0621 (14)	0.0529 (13)	0.0077 (10)	0.0134 (9)	−0.0006 (10)

Geometric parameters (Å, º)

O1—C1	1.203 (3)	C10—C11	1.524 (3)
O2—C4	1.206 (2)	C13—C14	1.490 (3)
O3—N1	1.387 (2)	C14—C15	1.304 (3)
O3—C5	1.395 (2)	C15—C16	1.488 (3)
O4—C5	1.187 (3)	C2—H2A	0.9500
O5—C13	1.202 (3)	C2—H2B	0.9500
O6—C16	1.206 (3)	C3—H3A	0.9500
N1—C1	1.379 (3)	C3—H3B	0.9500
N1—C4	1.376 (2)	C6—H6	0.9500
N2—C12	1.463 (2)	C7—H7A	0.9500
N2—C13	1.389 (3)	C7—H7B	0.9500
N2—C16	1.380 (3)	C8—H8A	0.9600
C1—C2	1.486 (3)	C8—H8B	0.9500
C2—C3	1.515 (3)	C9—H9	0.9500
C3—C4	1.494 (3)	C10—H10A	0.9500
C5—C6	1.489 (3)	C10—H10B	0.9500
C6—C7	1.525 (3)	C11—H11A	0.9500
C6—C11	1.530 (3)	C11—H11B	0.9500
C7—C8	1.520 (3)	C12—H12A	0.9500
C8—C9	1.522 (3)	C12—H12B	0.9400
C9—C10	1.521 (3)	C14—H14	0.9500
C9—C12	1.523 (3)	C15—H15	0.9600
O1···O3	2.784 (2)	C2···H8B^ix	3.0200
O1···C5	3.344 (3)	C3···H10B^iv	3.0700
O1···C14^i	3.330 (3)	C4···H2A^iii	3.0500
O1···C7^ii	3.386 (3)	C9···H2B^v	3.0000
O2···C2^iii	3.381 (3)	C13···H11A^xi	2.9900
O2···C16^iv	3.257 (3)	C15···H15^xii	3.0300
O2···O3	2.798 (2)	C16···H10B	2.8800
O2···C15^iv	3.182 (3)	H2A···H8B^ix	2.5700
O3···O1	2.784 (2)	H2A···O2^ii	2.5000
O3···O2	2.798 (2)	H2A···O3^ii	2.8200
O4···N1	2.559 (2)	H2A···C4^ii	3.0500
O4···C1	3.181 (3)	H2B···O6^viii	2.5800
O4···C4	3.273 (3)	H2B···C9^ix	3.0000
O5···C3^v	3.338 (3)	H2B···H9^ix	2.3200
O6···C3^vi	3.335 (3)	H3A···O6^iv	2.5200
O6···N1^vii	3.202 (2)	H3B···O5^ix	2.6600
O6···C10	3.337 (3)	H6···H8A	2.5300
O6···C1^vii	2.935 (3)	H6···H10A	2.5900
O6···C3^vii	3.314 (3)	H7A···H9	2.5400
O6···C2^vii	3.033 (3)	H7A···H11A	2.5700
O1···H14^i	2.4200	H7B···O3	2.8700
O1···H7B^ii	2.6900	H7B···O1^iii	2.6900
O2···H2A^iii	2.5000	H8A···H6	2.5300
O2···H10B^iv	2.7900	H8A···H10A	2.5600
O3···H2A^iii	2.8200	H8A···H12A	2.5200
O3···H7B	2.8700	H8B···H12B	2.4300
O4···H11A	2.7000	H8B···C2^v	3.0200
O5···H12B	2.6900	H8B···H2A^v	2.5700
O5···H3B^v	2.6600	H9···H7A	2.5400
O6···H2B^vii	2.5800	H9···H11A	2.5800
O6···H12A	2.6000	H9···H2B^v	2.3200
O6···H3A^vi	2.5200	H10A···H6	2.5900
N1···O4	2.559 (2)	H10A···H8A	2.5600
N1···O6^viii	3.202 (2)	H10A···H12A	2.5300
N2···H10B	2.7400	H10B···N2	2.7400
C1···O4	3.181 (3)	H10B···C16	2.8800
C1···O6^viii	2.935 (3)	H10B···O2^vi	2.7900
C2···O6^viii	3.033 (3)	H10B···C3^vi	3.0700
C2···O2^ii	3.381 (3)	H11A···O4	2.7000
C3···O5^ix	3.338 (3)	H11A···H7A	2.5700
C3···O6^viii	3.314 (3)	H11A···H9	2.5800
C3···O6^iv	3.335 (3)	H11A···C13^xiii	2.9900
C4···O4	3.273 (3)	H12A···O6	2.6000
C5···O1	3.344 (3)	H12A···H8A	2.5200
C7···O1^iii	3.386 (3)	H12A···H10A	2.5300
C10···C16	3.394 (3)	H12B···O5	2.6900
C10···O6	3.337 (3)	H12B···H8B	2.4300
C14···O1^x	3.330 (3)	H14···O1^x	2.4200
C15···O2^vi	3.182 (3)	H15···C15^xii	3.0300
C16···C10	3.394 (3)	H15···H15^xii	2.5300
C16···O2^vi	3.257 (3)
N1—O3—C5	112.53 (14)	H2A—C2—H2B	109.00
O3—N1—C1	121.31 (15)	C2—C3—H3A	110.00
O3—N1—C4	122.07 (15)	C2—C3—H3B	110.00
C1—N1—C4	116.49 (16)	C4—C3—H3A	111.00
C12—N2—C13	125.11 (16)	C4—C3—H3B	111.00
C12—N2—C16	124.65 (16)	H3A—C3—H3B	109.00
C13—N2—C16	110.20 (16)	C5—C6—H6	108.00
O1—C1—N1	124.28 (19)	C7—C6—H6	109.00
O1—C1—C2	130.10 (19)	C11—C6—H6	109.00
N1—C1—C2	105.62 (16)	C6—C7—H7A	109.00
C1—C2—C3	106.23 (16)	C6—C7—H7B	109.00
C2—C3—C4	105.95 (16)	C8—C7—H7A	109.00
O2—C4—N1	124.30 (18)	C8—C7—H7B	110.00
O2—C4—C3	130.14 (18)	H7A—C7—H7B	109.00
N1—C4—C3	105.55 (16)	C7—C8—H8A	108.00
O3—C5—O4	121.40 (18)	C7—C8—H8B	109.00
O3—C5—C6	109.01 (15)	C9—C8—H8A	109.00
O4—C5—C6	129.57 (19)	C9—C8—H8B	109.00
C5—C6—C7	109.67 (16)	H8A—C8—H8B	109.00
C5—C6—C11	110.87 (16)	C8—C9—H9	108.00
C7—C6—C11	110.59 (16)	C10—C9—H9	107.00
C6—C7—C8	110.51 (15)	C12—C9—H9	108.00
C7—C8—C9	111.93 (15)	C9—C10—H10A	109.00
C8—C9—C10	110.15 (15)	C9—C10—H10B	109.00
C8—C9—C12	110.05 (15)	C11—C10—H10A	108.00
C10—C9—C12	112.99 (15)	C11—C10—H10B	109.00
C9—C10—C11	112.09 (15)	H10A—C10—H10B	109.00
C6—C11—C10	111.33 (16)	C6—C11—H11A	109.00
N2—C12—C9	113.96 (15)	C6—C11—H11B	109.00
O5—C13—N2	124.8 (2)	C10—C11—H11A	109.00
O5—C13—C14	129.4 (2)	C10—C11—H11B	109.00
N2—C13—C14	105.81 (18)	H11A—C11—H11B	109.00
C13—C14—C15	108.86 (19)	N2—C12—H12A	108.00
C14—C15—C16	109.04 (18)	N2—C12—H12B	108.00
O6—C16—N2	125.10 (17)	C9—C12—H12A	108.00
O6—C16—C15	128.83 (19)	C9—C12—H12B	109.00
N2—C16—C15	106.06 (18)	H12A—C12—H12B	110.00
C1—C2—H2A	110.00	C13—C14—H14	126.00
C1—C2—H2B	110.00	C15—C14—H14	125.00
C3—C2—H2A	111.00	C14—C15—H15	126.00
C3—C2—H2B	110.00	C16—C15—H15	125.00
C5—O3—N1—C1	−88.6 (2)	C1—C2—C3—C4	−3.8 (2)
C5—O3—N1—C4	95.7 (2)	C2—C3—C4—O2	−177.9 (2)
N1—O3—C5—O4	−1.1 (3)	C2—C3—C4—N1	2.2 (2)
N1—O3—C5—C6	−179.35 (15)	O3—C5—C6—C7	87.80 (19)
O3—N1—C1—O1	2.1 (3)	O3—C5—C6—C11	−149.79 (16)
O3—N1—C1—C2	−178.74 (15)	O4—C5—C6—C11	32.1 (3)
C4—N1—C1—O1	178.0 (2)	O4—C5—C6—C7	−90.3 (3)
C4—N1—C1—C2	−2.8 (2)	C5—C6—C7—C8	178.92 (15)
O3—N1—C4—O2	−3.7 (3)	C11—C6—C7—C8	56.3 (2)
O3—N1—C4—C3	176.27 (15)	C5—C6—C11—C10	−177.11 (16)
C1—N1—C4—O2	−179.54 (19)	C7—C6—C11—C10	−55.2 (2)
C1—N1—C4—C3	0.4 (2)	C6—C7—C8—C9	−57.5 (2)
C13—N2—C12—C9	−87.4 (2)	C7—C8—C9—C12	−178.71 (15)
C16—N2—C12—C9	95.3 (2)	C7—C8—C9—C10	56.1 (2)
C12—N2—C13—O5	2.8 (3)	C12—C9—C10—C11	−178.11 (15)
C12—N2—C13—C14	−177.76 (17)	C8—C9—C12—N2	175.92 (15)
C16—N2—C13—O5	−179.6 (2)	C8—C9—C10—C11	−54.6 (2)
C16—N2—C13—C14	−0.1 (2)	C10—C9—C12—N2	−60.5 (2)
C12—N2—C16—O6	−0.6 (3)	C9—C10—C11—C6	54.9 (2)
C12—N2—C16—C15	178.66 (18)	O5—C13—C14—C15	178.5 (2)
C13—N2—C16—O6	−178.3 (2)	N2—C13—C14—C15	−1.0 (2)
C13—N2—C16—C15	1.0 (2)	C13—C14—C15—C16	1.6 (3)
N1—C1—C2—C3	4.0 (2)	C14—C15—C16—O6	177.6 (2)
O1—C1—C2—C3	−176.9 (2)	C14—C15—C16—N2	−1.7 (3)

Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) x, −y+1/2, z−1/2; (iii) x, −y+1/2, z+1/2; (iv) x+1/2, y, −z+3/2; (v) −x+2, y+1/2, −z+3/2; (vi) x−1/2, y, −z+3/2; (vii) x−1/2, −y+1/2, −z+2; (viii) x+1/2, −y+1/2, −z+2; (ix) −x+2, y−1/2, −z+3/2; (x) −x+3/2, y+1/2, z; (xi) −x+3/2, −y+1, z+1/2; (xii) −x+1, −y+1, −z+2; (xiii) −x+3/2, −y+1, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2^ii	0.95	2.50	3.381 (3)	154
C2—H2B···O6^viii	0.95	2.58	3.033 (3)	109
C3—H3A···O6^iv	0.95	2.52	3.335 (3)	144
C12—H12A···O6	0.95	2.60	2.913 (3)	100
C14—H14···O1^x	0.95	2.42	3.330 (3)	160

Symmetry codes: (ii) x, −y+1/2, z−1/2; (iv) x+1/2, y, −z+3/2; (viii) x+1/2, −y+1/2, −z+2; (x) −x+3/2, y+1/2, z.