7-Iso-propyl-idene-N (2),N (3),N (5),N (6)-tetra-meth-oxy-N (2),N (3),N (5),N (6)-tetra-methylbi-cyclo-[2.2.1]hepta-2,5-diene-2,3,5,6-tetra-carboxamide.

Although the mol-ecular structure of the title compound, C22H32N4O8, displays a twofold symmetry of the mol-ecule including the meth-oxy and methyl substituents, no crystallographic twofold symmetry is observed in the X-ray structure analysis. The carbonyl O atoms alternately point to different sides of the plane defined by the carbonyl C atoms. Two meth-oxy groups are oriented inside the mol-ecules cavity. The H atoms of two methyl groups are disordered over two orientations and were refined using a split model.

Related literature

For background to this work, see: Winkler et al. (2003a ▶, 2012 ▶). For the structure of 7-iso­propyl­idenenorborna-2,5-diene-2,3,5,6-tetra­carb­oxy­lic acid tetra­kis­(di­ethyl­amide), see: Winkler et al. (2003b ▶).

Experimental

Crystal data

C22H32N4O8

M = 480.52

Triclinic,

a = 9.5830 (9) Å

b = 10.2662 (8) Å

c = 13.3792 (16) Å

α = 94.648 (12)°

β = 91.548 (13)°

γ = 108.013 (10)°

V = 1245.7 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 200 K

0.3 × 0.3 × 0.2 mm

Data collection

Stoe IPDS-1 diffractometer

10017 measured reflections

4788 independent reflections

3431 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.119

S = 1.00

4788 reflections

318 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.19 e Å−3

Data collection: X-AREA (Stoe & Cie, 2008 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: XCIF in SHELXTL.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814004255/im2450sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814004255/im2450Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814004255/im2450Isup3.cml

CCDC reference: 878002

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H32N4O8	Z = 2
Mr = 480.52	F(000) = 512
Triclinic, P1	Dx = 1.281 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5830 (9) Å	Cell parameters from 3915 reflections
b = 10.2662 (8) Å	θ = 4–28°
c = 13.3792 (16) Å	µ = 0.10 mm−1
α = 94.648 (12)°	T = 200 K
β = 91.548 (13)°	Block, colorless
γ = 108.013 (10)°	0.3 × 0.3 × 0.2 mm
V = 1245.7 (2) Å3

Stoe IPDS-1 diffractometer	3431 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
Graphite monochromator	θmax = 26.0°, θmin = 2.9°
Phi scans	h = −11→11
10017 measured reflections	k = −12→12
4788 independent reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0701P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
4788 reflections	Δρmax = 0.19 e Å−3
318 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.079 (8)

Experimental. 1H-NMR (500 MHz, 300 K, CDCl3, TMS): δ = 4.65 (s, 2H, H-1,4), 3.62 (s, 12H, H12), 3.25 (s, 12H, H-11), 1.53 (s, 6H, H-9) p.p.m.. 13C-NMR (125 MHz, 300 K, CDCl3, TMS): δ = 165.8 (C-10), 160.5 (C-7), 151.1 (C-2,3,5,6), 100.4 (C-8), 61.6 (C-12), 56.5 (C-1,4), 32.1 (C-11), 18.3 (C-9) p.p.m.. MS (EI, 70 eV): m/z(%)= 480 (2) [M]+, 421 (24), 420 (100), 329 (14), 328 (13), 269 (13), 268 (46), 240 (21), 220 (26). MS (CI, isobutane): m/z(%)= 481 (100) [M+H]+. UV/Vis (CHCl3): λ(max)(lg ε)= 262 nm (3.855), 314 nm (2.881).

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.81447 (18)	0.39743 (16)	0.81937 (12)	0.0298 (3)
C2	0.67642 (18)	0.36772 (16)	0.78212 (13)	0.0300 (3)
C3	0.63158 (18)	0.21966 (17)	0.73104 (13)	0.0308 (4)
H3	0.5240	0.1707	0.7187	0.037*
C4	0.72948 (19)	0.21953 (16)	0.64136 (13)	0.0301 (3)
C5	0.86786 (18)	0.24874 (16)	0.67833 (12)	0.0295 (3)
C6	0.86494 (18)	0.27007 (16)	0.79390 (13)	0.0302 (3)
H6	0.9515	0.2636	0.8343	0.036*
C7	0.71645 (19)	0.15921 (17)	0.80360 (13)	0.0319 (4)
C8	0.6783 (2)	0.04726 (18)	0.85174 (13)	0.0386 (4)
C9	0.5221 (3)	−0.0464 (2)	0.84862 (16)	0.0501 (5)
H9A	0.4600	−0.0117	0.8055	0.075*
H9B	0.4866	−0.0493	0.9167	0.075*
H9C	0.5180	−0.1393	0.8217	0.075*
C10	0.7892 (3)	0.0025 (2)	0.91079 (16)	0.0505 (5)
H10A	0.8882	0.0643	0.9024	0.076*
H10B	0.7832	−0.0917	0.8862	0.076*
H10C	0.7682	0.0059	0.9821	0.076*
C11	0.89827 (19)	0.52489 (18)	0.88315 (13)	0.0341 (4)
O1	0.85560 (18)	0.55873 (16)	0.96400 (11)	0.0500 (4)
N1	1.02489 (18)	0.60006 (17)	0.84779 (12)	0.0404 (4)
C12	1.1278 (3)	0.7203 (2)	0.90131 (19)	0.0544 (5)
H12A	1.0857	0.7446	0.9633	0.082*	0.60
H12B	1.1485	0.7971	0.8592	0.082*	0.60
H12C	1.2193	0.7010	0.9178	0.082*	0.60
H12D	1.2166	0.7505	0.8636	0.082*	0.40
H12E	1.1539	0.6980	0.9677	0.082*	0.40
H12F	1.0831	0.7942	0.9091	0.082*	0.40
O2	1.06466 (14)	0.55339 (13)	0.75543 (10)	0.0359 (3)
C13	1.0318 (3)	0.6292 (2)	0.67700 (16)	0.0481 (5)
H13A	0.9303	0.6306	0.6808	0.072*
H13B	1.0437	0.5849	0.6115	0.072*
H13C	1.0990	0.7237	0.6853	0.072*
C14	0.58711 (19)	0.46339 (18)	0.78346 (13)	0.0335 (4)
O3	0.63333 (18)	0.57977 (14)	0.75583 (12)	0.0502 (4)
N2	0.45160 (17)	0.41573 (17)	0.81724 (13)	0.0403 (4)
C15	0.3392 (2)	0.4826 (3)	0.81249 (18)	0.0535 (5)
H15A	0.3831	0.5771	0.7954	0.080*
H15B	0.2957	0.4839	0.8778	0.080*
H15C	0.2627	0.4319	0.7610	0.080*
O4	0.40977 (16)	0.28673 (14)	0.85165 (12)	0.0482 (4)
C16	0.4368 (4)	0.3012 (3)	0.9592 (2)	0.0717 (8)
H16A	0.5405	0.3524	0.9763	0.108*
H16B	0.4134	0.2099	0.9837	0.108*
H16C	0.3749	0.3512	0.9908	0.108*
C17	0.6746 (2)	0.17624 (18)	0.53508 (13)	0.0354 (4)
O5	0.7086 (2)	0.08738 (17)	0.48378 (11)	0.0580 (4)
N3	0.57718 (19)	0.23375 (16)	0.49947 (12)	0.0396 (4)
C18	0.5110 (3)	0.2035 (3)	0.39838 (16)	0.0542 (5)
H18A	0.4217	0.2308	0.3958	0.081*	0.60
H18B	0.4859	0.1046	0.3786	0.081*	0.60
H18C	0.5807	0.2546	0.3522	0.081*	0.60
H18D	0.5705	0.1625	0.3553	0.081*	0.40
H18E	0.5063	0.2887	0.3725	0.081*	0.40
H18F	0.4115	0.1387	0.3989	0.081*	0.40
O6	0.56596 (14)	0.35176 (13)	0.55432 (10)	0.0365 (3)
C19	0.6728 (2)	0.4717 (2)	0.52256 (16)	0.0458 (5)
H19A	0.7707	0.4607	0.5275	0.069*
H19B	0.6721	0.5533	0.5658	0.069*
H19C	0.6484	0.4829	0.4528	0.069*
C20	1.00122 (19)	0.26034 (17)	0.62073 (14)	0.0341 (4)
O7	1.03798 (18)	0.33922 (16)	0.55533 (12)	0.0524 (4)
N4	1.08090 (18)	0.18055 (17)	0.64597 (14)	0.0440 (4)
C21	1.2220 (2)	0.1841 (3)	0.6077 (2)	0.0571 (6)
H21A	1.2963	0.2065	0.6636	0.086*
H21B	1.2503	0.2543	0.5601	0.086*
H21C	1.2149	0.0940	0.5735	0.086*
O8	1.02474 (18)	0.08363 (15)	0.71379 (11)	0.0482 (4)
C22	0.9419 (3)	−0.0452 (2)	0.6592 (2)	0.0641 (7)
H22A	0.8626	−0.0316	0.6176	0.096*
H22B	0.8998	−0.1127	0.7067	0.096*
H22C	1.0070	−0.0787	0.6160	0.096*

	U11	U22	U33	U12	U13	U23
C1	0.0281 (8)	0.0296 (8)	0.0321 (8)	0.0086 (6)	0.0069 (7)	0.0048 (6)
C2	0.0280 (8)	0.0302 (8)	0.0329 (8)	0.0100 (6)	0.0074 (7)	0.0046 (6)
C3	0.0276 (8)	0.0304 (8)	0.0345 (8)	0.0083 (6)	0.0046 (7)	0.0044 (6)
C4	0.0324 (8)	0.0270 (7)	0.0340 (8)	0.0126 (6)	0.0055 (7)	0.0057 (6)
C5	0.0325 (8)	0.0260 (7)	0.0343 (8)	0.0139 (6)	0.0072 (7)	0.0068 (6)
C6	0.0278 (8)	0.0298 (8)	0.0345 (8)	0.0103 (6)	0.0035 (7)	0.0063 (6)
C7	0.0342 (9)	0.0296 (8)	0.0327 (8)	0.0103 (7)	0.0049 (7)	0.0045 (6)
C8	0.0508 (11)	0.0304 (8)	0.0314 (8)	0.0079 (8)	0.0054 (8)	0.0028 (7)
C9	0.0607 (13)	0.0370 (9)	0.0391 (10)	−0.0051 (9)	0.0060 (9)	0.0051 (8)
C10	0.0727 (15)	0.0383 (10)	0.0409 (10)	0.0163 (10)	−0.0020 (10)	0.0119 (8)
C11	0.0319 (9)	0.0348 (8)	0.0361 (9)	0.0112 (7)	0.0035 (7)	0.0034 (7)
O1	0.0539 (9)	0.0508 (8)	0.0419 (8)	0.0134 (7)	0.0120 (7)	−0.0069 (6)
N1	0.0347 (8)	0.0413 (8)	0.0370 (8)	0.0016 (6)	0.0022 (7)	−0.0029 (6)
C12	0.0439 (12)	0.0444 (11)	0.0608 (13)	−0.0028 (9)	−0.0015 (10)	−0.0091 (10)
O2	0.0321 (6)	0.0378 (6)	0.0402 (7)	0.0133 (5)	0.0062 (5)	0.0065 (5)
C13	0.0540 (12)	0.0472 (11)	0.0474 (11)	0.0191 (9)	0.0053 (9)	0.0147 (9)
C14	0.0330 (9)	0.0386 (9)	0.0322 (8)	0.0157 (7)	0.0058 (7)	0.0043 (7)
O3	0.0551 (9)	0.0389 (7)	0.0660 (9)	0.0240 (6)	0.0220 (7)	0.0156 (7)
N2	0.0333 (8)	0.0482 (9)	0.0475 (9)	0.0210 (7)	0.0119 (7)	0.0148 (7)
C15	0.0409 (11)	0.0715 (14)	0.0590 (13)	0.0354 (11)	0.0030 (10)	−0.0013 (11)
O4	0.0421 (8)	0.0422 (7)	0.0591 (9)	0.0097 (6)	0.0181 (7)	0.0065 (6)
C16	0.100 (2)	0.0689 (16)	0.0577 (15)	0.0341 (15)	0.0352 (15)	0.0287 (13)
C17	0.0401 (9)	0.0314 (8)	0.0363 (9)	0.0137 (7)	0.0036 (7)	0.0015 (7)
O5	0.0851 (12)	0.0572 (9)	0.0439 (8)	0.0443 (9)	−0.0027 (8)	−0.0100 (7)
N3	0.0459 (9)	0.0369 (8)	0.0373 (8)	0.0169 (7)	−0.0064 (7)	−0.0024 (6)
C18	0.0593 (14)	0.0574 (13)	0.0419 (11)	0.0152 (11)	−0.0148 (10)	−0.0004 (9)
O6	0.0350 (7)	0.0360 (6)	0.0417 (7)	0.0153 (5)	0.0043 (5)	0.0050 (5)
C19	0.0511 (12)	0.0370 (9)	0.0491 (11)	0.0115 (8)	0.0054 (9)	0.0109 (8)
C20	0.0327 (9)	0.0320 (8)	0.0402 (9)	0.0140 (7)	0.0066 (7)	0.0007 (7)
O7	0.0570 (9)	0.0550 (9)	0.0540 (9)	0.0244 (7)	0.0276 (7)	0.0211 (7)
N4	0.0372 (9)	0.0429 (8)	0.0589 (10)	0.0215 (7)	0.0097 (8)	0.0075 (7)
C21	0.0368 (11)	0.0684 (14)	0.0708 (15)	0.0283 (10)	0.0042 (10)	−0.0142 (11)
O8	0.0591 (9)	0.0453 (8)	0.0506 (8)	0.0309 (7)	0.0012 (7)	0.0072 (6)
C22	0.0818 (18)	0.0351 (10)	0.0781 (17)	0.0223 (11)	0.0060 (14)	0.0040 (10)

C1—C2	1.335 (3)	C14—O3	1.230 (2)
C1—C11	1.489 (2)	C14—N2	1.343 (2)
C1—C6	1.545 (2)	N2—O4	1.381 (2)
C2—C14	1.488 (2)	N2—C15	1.447 (2)
C2—C3	1.541 (2)	C15—H15A	0.9800
C3—C7	1.535 (2)	C15—H15B	0.9800
C3—C4	1.543 (2)	C15—H15C	0.9800
C3—H3	1.0000	O4—C16	1.443 (3)
C4—C5	1.337 (3)	C16—H16A	0.9800
C4—C17	1.486 (3)	C16—H16B	0.9800
C5—C20	1.488 (2)	C16—H16C	0.9800
C5—C6	1.546 (2)	C17—O5	1.226 (2)
C6—C7	1.539 (2)	C17—N3	1.345 (2)
C6—H6	1.0000	N3—O6	1.400 (2)
C7—C8	1.320 (2)	N3—C18	1.446 (3)
C8—C9	1.506 (3)	C18—H18A	0.9800
C8—C10	1.510 (3)	C18—H18B	0.9800
C9—H9A	0.9800	C18—H18C	0.9800
C9—H9B	0.9800	C18—H18D	0.9800
C9—H9C	0.9800	C18—H18E	0.9800
C10—H10A	0.9800	C18—H18F	0.9800
C10—H10B	0.9800	O6—C19	1.440 (2)
C10—H10C	0.9800	C19—H19A	0.9800
C11—O1	1.228 (2)	C19—H19B	0.9800
C11—N1	1.343 (2)	C19—H19C	0.9800
N1—O2	1.394 (2)	C20—O7	1.225 (2)
N1—C12	1.441 (3)	C20—N4	1.336 (2)
C12—H12A	0.9800	N4—O8	1.394 (2)
C12—H12B	0.9800	N4—C21	1.450 (2)
C12—H12C	0.9800	C21—H21A	0.9800
C12—H12D	0.9800	C21—H21B	0.9800
C12—H12E	0.9800	C21—H21C	0.9800
C12—H12F	0.9800	O8—C22	1.441 (3)
O2—C13	1.440 (2)	C22—H22A	0.9800
C13—H13A	0.9800	C22—H22B	0.9800
C13—H13B	0.9800	C22—H22C	0.9800
C13—H13C	0.9800
C2—C1—C11	125.72 (15)	H13A—C13—H13C	109.5
C2—C1—C6	107.71 (14)	H13B—C13—H13C	109.5
C11—C1—C6	126.28 (15)	O3—C14—N2	121.23 (16)
C1—C2—C14	126.22 (16)	O3—C14—C2	122.67 (15)
C1—C2—C3	107.02 (14)	N2—C14—C2	116.10 (15)
C14—C2—C3	126.62 (15)	C14—N2—O4	118.04 (14)
C7—C3—C2	98.31 (13)	C14—N2—C15	125.53 (17)
C7—C3—C4	96.76 (12)	O4—N2—C15	116.18 (16)
C2—C3—C4	107.50 (13)	N2—C15—H15A	109.5
C7—C3—H3	117.0	N2—C15—H15B	109.5
C2—C3—H3	117.0	H15A—C15—H15B	109.5
C4—C3—H3	117.0	N2—C15—H15C	109.5
C5—C4—C17	126.88 (15)	H15A—C15—H15C	109.5
C5—C4—C3	107.59 (15)	H15B—C15—H15C	109.5
C17—C4—C3	125.07 (15)	N2—O4—C16	108.98 (17)
C4—C5—C20	127.32 (16)	O4—C16—H16A	109.5
C4—C5—C6	107.01 (14)	O4—C16—H16B	109.5
C20—C5—C6	125.67 (15)	H16A—C16—H16B	109.5
C7—C6—C1	97.69 (12)	O4—C16—H16C	109.5
C7—C6—C5	96.70 (13)	H16A—C16—H16C	109.5
C1—C6—C5	107.58 (12)	H16B—C16—H16C	109.5
C7—C6—H6	117.2	O5—C17—N3	121.17 (18)
C1—C6—H6	117.2	O5—C17—C4	122.52 (16)
C5—C6—H6	117.2	N3—C17—C4	116.18 (15)
C8—C7—C3	132.86 (17)	C17—N3—O6	117.33 (15)
C8—C7—C6	132.60 (17)	C17—N3—C18	124.05 (17)
C3—C7—C6	94.40 (13)	O6—N3—C18	116.83 (15)
C7—C8—C9	122.14 (19)	N3—C18—H18A	109.5
C7—C8—C10	122.15 (19)	N3—C18—H18B	109.5
C9—C8—C10	115.68 (17)	H18A—C18—H18B	109.5
C8—C9—H9A	109.5	N3—C18—H18C	109.5
C8—C9—H9B	109.5	H18A—C18—H18C	109.5
H9A—C9—H9B	109.5	H18B—C18—H18C	109.5
C8—C9—H9C	109.5	N3—C18—H18D	109.5
H9A—C9—H9C	109.5	N3—C18—H18E	109.5
H9B—C9—H9C	109.5	H18D—C18—H18E	109.5
C8—C10—H10A	109.5	N3—C18—H18F	109.5
C8—C10—H10B	109.5	H18D—C18—H18F	109.5
H10A—C10—H10B	109.5	H18E—C18—H18F	109.5
C8—C10—H10C	109.5	N3—O6—C19	109.55 (14)
H10A—C10—H10C	109.5	O6—C19—H19A	109.5
H10B—C10—H10C	109.5	O6—C19—H19B	109.5
O1—C11—N1	121.74 (18)	H19A—C19—H19B	109.5
O1—C11—C1	122.24 (16)	O6—C19—H19C	109.5
N1—C11—C1	116.02 (15)	H19A—C19—H19C	109.5
C11—N1—O2	117.70 (15)	H19B—C19—H19C	109.5
C11—N1—C12	124.80 (17)	O7—C20—N4	121.58 (16)
O2—N1—C12	117.35 (15)	O7—C20—C5	122.68 (15)
N1—C12—H12A	109.5	N4—C20—C5	115.73 (15)
N1—C12—H12B	109.5	C20—N4—O8	118.28 (15)
H12A—C12—H12B	109.5	C20—N4—C21	125.56 (18)
N1—C12—H12C	109.5	O8—N4—C21	116.16 (17)
H12A—C12—H12C	109.5	N4—C21—H21A	109.5
H12B—C12—H12C	109.5	N4—C21—H21B	109.5
N1—C12—H12D	109.5	H21A—C21—H21B	109.5
N1—C12—H12E	109.5	N4—C21—H21C	109.5
H12D—C12—H12E	109.5	H21A—C21—H21C	109.5
N1—C12—H12F	109.5	H21B—C21—H21C	109.5
H12D—C12—H12F	109.5	N4—O8—C22	109.25 (17)
H12E—C12—H12F	109.5	O8—C22—H22A	109.5
N1—O2—C13	110.50 (14)	O8—C22—H22B	109.5
O2—C13—H13A	109.5	H22A—C22—H22B	109.5
O2—C13—H13B	109.5	O8—C22—H22C	109.5
H13A—C13—H13B	109.5	H22A—C22—H22C	109.5
O2—C13—H13C	109.5	H22B—C22—H22C	109.5