3-(tert-Butyl­oxy­carbonyl­amino)­bicyclo­[1.1.1]­pentane­carboxyl­ic acid at 293 K

In the room-temperature X-ray structure of the N-Boc-protected derivative of the novel 3-amino­bi­cyclo[1.1.1]­pentanecarboxyl­ic acid, C₁₁H₁₇NO₄, the interbridgehead distance in the bi­cyclo­[1.1.1]­pentane cage is 1.852 (2) Å. The carboxyl and parts of the blocked amino group are almost in plane with one of the cage triangles. N-H...O and O-H...O hydrogen bonds generate infinite corrugated molecular chains in the crystal lattice.

Computing details

Data collection: SMART (Siemens, 1996a); cell refinement: SMART; data reduction: SHELXTL (Siemens, 1996b) and SAINT-Plus (Siemens, 1996a); program(s) used to solve structure: SHELXS86 (Sheldrick, 1987); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SCHAKAL88 (Keller, 1988) and ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 1990).

(IIa)

Crystal data

C11H17NO4	F(000) = 488
Mr = 227.26	Dx = 1.194 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71068 Å
a = 6.0851 (2) Å	Cell parameters from 10385 reflections
b = 18.3460 (4) Å	θ = 2.2–32.1°
c = 11.3499 (6) Å	µ = 0.09 mm^−1
β = 94.020 (3)°	T = 293 K
V = 1263.95 (8) Å^3	Prism, yellow
Z = 4	0.40 × 0.40 × 0.18 mm

Data collection

CCD area detector diffractometer	2444 reflections with F > 4σ(Fo)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 32.1°, θmin = 2.2°
ω, φ scans	h = −8→8
10385 measured reflections	k = −24→27
4017 independent reflections	l = −16→16

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0754P)^2 + 0.0246P] where P = (Fo^2 + 2Fc^2)/3
4017 reflections	(Δ/σ)max < 0.001
149 parameters	Δρmax = 0.31 e Å^−3
2 restraints	Δρmin = −0.16 e Å^−3

Special details

Experimental. The X-ray experiments were executed with a Bruker SMART-CCD area detection diffractometer. First standard measurement strategy, (3 runs at 450 frames each, 2θ fixed at -32°, φ-positions 0°, 90°, 240°, Δω increments 0.4°, 20 sec exposure time per frame, crystal-to-detector distance 40 mm) was followed. A fourth run was added at 2θ= 0° and 600 frames of Δφ increments of 0.4°, 20 sec exposure time.

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
C1	0.6724 (3)	0.48856 (9)	1.09350 (15)	0.0433 (4)
C2	0.5132 (4)	0.42525 (16)	1.1156 (2)	0.0776 (7)
H21	0.5803	0.3778	1.1294	0.093*
H22	0.3978	0.4357	1.1678	0.093*
C3	0.4660 (3)	0.44724 (9)	0.98581 (16)	0.0446 (4)
N1	0.3009 (2)	0.41966 (8)	0.90099 (15)	0.0564 (4)
H1	0.1942	0.4484	0.8791	0.068*
C4	0.4734 (4)	0.52659 (13)	1.0284 (3)	0.0810 (8)
H41	0.3562	0.5415	1.0768	0.097*
H42	0.5073	0.5629	0.9702	0.097*
C5	0.7133 (4)	0.45168 (18)	0.9768 (2)	0.0800 (8)
H51	0.7624	0.4832	0.9153	0.096*
H52	0.7923	0.4057	0.9825	0.096*
C6	0.2986 (3)	0.35315 (11)	0.85311 (17)	0.0525 (5)
O3	0.4566 (2)	0.31055 (7)	0.90169 (12)	0.0598 (4)
O4	0.1630 (2)	0.33386 (8)	0.77416 (14)	0.0750 (5)
C7	0.4902 (3)	0.23573 (10)	0.85875 (19)	0.0582 (5)
C8	0.6815 (5)	0.21041 (16)	0.9430 (3)	0.0943 (9)
H81	0.8092	0.2395	0.9313	0.141*
H82	0.7134	0.1602	0.9276	0.141*
H83	0.6423	0.2156	1.0230	0.141*
C9	0.2922 (5)	0.18900 (14)	0.8743 (3)	0.0800 (7)
H91	0.2435	0.1961	0.9521	0.120*
H92	0.3301	0.1387	0.8641	0.120*
H93	0.1761	0.2023	0.8166	0.120*
C10	0.5564 (6)	0.23737 (19)	0.7332 (3)	0.0952 (9)
H101	0.4338	0.2532	0.6818	0.143*
H102	0.6004	0.1894	0.7106	0.143*
H103	0.6772	0.2705	0.7275	0.143*
C11	0.8454 (3)	0.52273 (9)	1.17379 (16)	0.0459 (4)
O1	0.8462 (3)	0.59364 (8)	1.16450 (18)	0.0856 (6)
H10	0.9558	0.6101	1.2014	0.103*
O2	0.9762 (2)	0.48964 (7)	1.23867 (13)	0.0609 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0427 (8)	0.0423 (8)	0.0437 (8)	−0.0002 (7)	−0.0055 (7)	−0.0038 (7)
C2	0.0786 (15)	0.0930 (17)	0.0588 (12)	−0.0345 (13)	−0.0115 (11)	0.0065 (12)
C3	0.0412 (8)	0.0408 (9)	0.0498 (9)	−0.0009 (7)	−0.0104 (7)	−0.0018 (7)
N1	0.0503 (9)	0.0446 (9)	0.0698 (11)	0.0076 (7)	−0.0272 (7)	−0.0060 (7)
C4	0.0790 (15)	0.0501 (12)	0.1067 (19)	0.0059 (11)	−0.0446 (14)	−0.0119 (12)
C5	0.0520 (12)	0.124 (2)	0.0628 (12)	−0.0101 (13)	−0.0018 (10)	−0.0369 (15)
C6	0.0478 (9)	0.0427 (10)	0.0637 (11)	0.0033 (7)	−0.0199 (8)	0.0001 (8)
O3	0.0623 (8)	0.0447 (7)	0.0673 (8)	0.0099 (6)	−0.0312 (6)	−0.0062 (6)
O4	0.0799 (10)	0.0468 (7)	0.0902 (10)	0.0102 (7)	−0.0504 (8)	−0.0088 (7)
C7	0.0596 (11)	0.0415 (10)	0.0705 (13)	0.0111 (8)	−0.0154 (9)	0.0002 (9)
C8	0.0858 (18)	0.0702 (16)	0.120 (2)	0.0314 (14)	−0.0394 (15)	0.0023 (15)
C9	0.0849 (17)	0.0511 (13)	0.1024 (18)	−0.0024 (11)	−0.0062 (14)	0.0009 (12)
C10	0.110 (2)	0.086 (2)	0.0890 (19)	0.0174 (16)	0.0058 (17)	−0.0034 (15)
C11	0.0486 (9)	0.0475 (9)	0.0405 (8)	−0.0042 (8)	−0.0037 (7)	−0.0032 (7)
O1	0.0934 (12)	0.0505 (8)	0.1036 (12)	−0.0150 (8)	−0.0601 (10)	0.0064 (8)
O2	0.0582 (8)	0.0555 (8)	0.0653 (8)	0.0007 (6)	−0.0218 (6)	−0.0005 (6)

Geometric parameters (Å, º)

C1—C11	1.482 (2)	C6—O3	1.329 (2)
C1—C5	1.524 (3)	O3—C7	1.476 (2)
C1—C4	1.541 (3)	C7—C9	1.499 (4)
C1—C2	1.544 (3)	C7—C10	1.508 (4)
C1—C3	1.852 (2)	C7—C8	1.526 (3)
C2—C3	1.535 (3)	C8—H81	0.9600
C2—H21	0.9700	C8—H82	0.9600
C2—H22	0.9700	C8—H83	0.9600
C3—N1	1.434 (2)	C9—H91	0.9600
C3—C5	1.517 (3)	C9—H92	0.9600
C3—C4	1.533 (3)	C9—H93	0.9600
N1—C6	1.335 (2)	C10—H101	0.9600
N1—H1	0.8600	C10—H102	0.9600
C4—H41	0.9700	C10—H103	0.9600
C4—H42	0.9700	C11—O2	1.209 (2)
C5—H51	0.9700	C11—O1	1.305 (2)
C5—H52	0.9700	O1—H10	0.8200
C6—O4	1.227 (2)
C11—C1—C5	124.76 (16)	C1—C5—H51	116.0
C11—C1—C4	127.15 (16)	C3—C5—H52	116.0
C5—C1—C4	87.39 (18)	C1—C5—H52	116.0
C11—C1—C2	130.16 (16)	H51—C5—H52	113.0
C5—C1—C2	87.11 (18)	O4—C6—O3	124.29 (17)
C4—C1—C2	86.43 (18)	O4—C6—N1	123.26 (17)
C11—C1—C3	176.63 (16)	O3—C6—N1	112.45 (15)
C5—C1—C3	52.33 (12)	C6—O3—C7	121.54 (14)
C4—C1—C3	52.77 (11)	O3—C7—C9	111.22 (18)
C2—C1—C3	52.78 (12)	O3—C7—C10	110.24 (19)
C3—C2—C1	73.98 (14)	C9—C7—C10	113.1 (2)
C3—C2—H21	116.1	O3—C7—C8	101.15 (18)
C1—C2—H21	116.1	C9—C7—C8	109.7 (2)
C3—C2—H22	116.1	C10—C7—C8	110.8 (2)
C1—C2—H22	116.1	C7—C8—H81	109.5
H21—C2—H22	113.1	C7—C8—H82	109.5
N1—C3—C5	128.66 (16)	H81—C8—H82	109.5
N1—C3—C4	123.37 (15)	C7—C8—H83	109.5
C5—C3—C4	87.88 (17)	H81—C8—H83	109.5
N1—C3—C2	128.81 (17)	H82—C8—H83	109.5
C5—C3—C2	87.66 (18)	C7—C9—H91	109.5
C4—C3—C2	87.02 (18)	C7—C9—H92	109.5
N1—C3—C1	176.47 (15)	H91—C9—H92	109.5
C5—C3—C1	52.63 (11)	C7—C9—H93	109.5
C4—C3—C1	53.14 (11)	H91—C9—H93	109.5
C2—C3—C1	53.24 (12)	H92—C9—H93	109.5
C6—N1—C3	125.64 (15)	C7—C10—H101	109.5
C6—N1—H1	117.2	C7—C10—H102	109.5
C3—N1—H1	117.2	H101—C10—H102	109.5
C3—C4—C1	74.09 (14)	C7—C10—H103	109.5
C3—C4—H41	116.1	H101—C10—H103	109.5
C1—C4—H41	116.1	H102—C10—H103	109.5
C3—C4—H42	116.1	O2—C11—O1	122.91 (16)
C1—C4—H42	116.1	O2—C11—C1	124.81 (16)
H41—C4—H42	113.1	O1—C11—C1	112.24 (15)
C3—C5—C1	75.04 (14)	C11—O1—H10	109.5
C3—C5—H51	116.0
C11—C1—C2—C3	−177.9 (2)	C2—C3—C4—C1	44.77 (17)
C5—C1—C2—C3	−43.11 (17)	C11—C1—C4—C3	175.77 (19)
C4—C1—C2—C3	44.45 (17)	C5—C1—C4—C3	42.80 (17)
C1—C2—C3—N1	−176.37 (19)	C2—C1—C4—C3	−44.46 (17)
C1—C2—C3—C5	43.31 (17)	N1—C3—C5—C1	175.84 (19)
C1—C2—C3—C4	−44.69 (16)	C4—C3—C5—C1	43.36 (17)
C11—C1—C3—N1	−82 (4)	C2—C3—C5—C1	−43.75 (18)
C5—C1—C3—N1	−113 (2)	C11—C1—C5—C3	−177.88 (18)
C4—C1—C3—N1	8 (2)	C4—C1—C5—C3	−43.11 (17)
C2—C1—C3—N1	127 (2)	C2—C1—C5—C3	43.44 (18)
C11—C1—C3—C5	31 (3)	C3—N1—C6—O4	−174.2 (2)
C4—C1—C3—C5	121.0 (2)	C3—N1—C6—O3	6.7 (3)
C2—C1—C3—C5	−120.4 (3)	O4—C6—O3—C7	3.5 (3)
C11—C1—C3—C4	−90 (3)	N1—C6—O3—C7	−177.36 (18)
C5—C1—C3—C4	−121.0 (2)	C6—O3—C7—C9	−62.4 (3)
C2—C1—C3—C4	118.6 (3)	C6—O3—C7—C10	64.0 (3)
C11—C1—C3—C2	151 (3)	C6—O3—C7—C8	−178.7 (2)
C5—C1—C3—C2	120.4 (3)	C5—C1—C11—O2	−76.3 (3)
C4—C1—C3—C2	−118.6 (2)	C4—C1—C11—O2	166.5 (2)
C5—C3—N1—C6	55.4 (3)	C2—C1—C11—O2	44.0 (3)
C4—C3—N1—C6	173.5 (2)	C3—C1—C11—O2	−106 (3)
C2—C3—N1—C6	−69.8 (3)	C5—C1—C11—O1	101.7 (3)
C1—C3—N1—C6	166 (2)	C4—C1—C11—O1	−15.4 (3)
N1—C3—C4—C1	−179.41 (18)	C2—C1—C11—O1	−137.9 (3)
C5—C3—C4—C1	−43.00 (17)	C3—C1—C11—O1	72 (3)