1,5-Di-tert-butyl-3-hydroxy-7-methyl­ene-1-azonia-5-aza­cyclo­octane iodide

This paper reports the solid-state structure of the title compound, C₁₅H₃₁IN₂O. The mol­ecule has a non-crystallographic mirror plane that accommodates all atoms except the hydroxyl-H and the H atom on the positively charged N atom.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.044
• wR factor = 0.117
• Data-to-parameter ratio = 21.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL.

(I)

Crystal data

C15H31IN2O	F(000) = 1568
Mr = 382.33	Dx = 1.357 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 26.8737 (10) Å	Cell parameters from 8072 reflections
b = 14.6191 (6) Å	θ = 2.5–28.2°
c = 10.1557 (4) Å	µ = 1.71 mm^−1
β = 110.323 (1)°	T = 294 K
V = 3741.5 (3) Å^3	Thick rod, colorless
Z = 8	0.48 × 0.40 × 0.16 mm

Data collection

Bruker SMART 1000 diffractometer	3821 independent reflections
Radiation source: normal-focus sealed tube	3074 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 8.3 pixels mm^-1	θmax = 26.4°, θmin = 1.6°
φ and ω scans	h = −33→32
Absorption correction: integration (XPREP; Bruker, 2001)	k = −18→18
Tmin = 0.757, Tmax = 0.815	l = −12→11
12311 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0613P)^2 + 9.4177P] where P = (Fo^2 + 2Fc^2)/3
3821 reflections	(Δ/σ)max = 0.010
178 parameters	Δρmax = 1.01 e Å^−3
0 restraints	Δρmin = −0.70 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
I1	0.394873 (13)	0.19912 (2)	1.45305 (3)	0.05592 (14)
N1	0.34829 (13)	0.3663 (2)	0.8567 (3)	0.0397 (7)
C1A	0.29039 (19)	0.3848 (4)	0.7784 (5)	0.0632 (14)
C1B	0.2741 (2)	0.3333 (6)	0.6383 (6)	0.105 (3)
H1BA	0.2373	0.3444	0.5864	0.157*
H1BB	0.2797	0.2689	0.6559	0.157*
H1BC	0.2952	0.3543	0.5849	0.157*
C1C	0.2790 (3)	0.4871 (5)	0.7506 (8)	0.104 (3)
H1CA	0.2418	0.4960	0.7008	0.156*
H1CB	0.2989	0.5100	0.6953	0.156*
H1CC	0.2893	0.5193	0.8384	0.156*
C1D	0.2587 (2)	0.3465 (6)	0.8644 (6)	0.0849 (19)
H1DA	0.2216	0.3579	0.8163	0.127*
H1DB	0.2698	0.3756	0.9547	0.127*
H1DC	0.2646	0.2818	0.8763	0.127*
C2	0.36913 (18)	0.4069 (3)	1.0003 (4)	0.0445 (9)
H2A	0.3419	0.4448	1.0151	0.053*
H2B	0.3994	0.4455	1.0082	0.053*
C3	0.38578 (18)	0.3329 (3)	1.1127 (4)	0.0434 (9)
H3A	0.3544	0.2981	1.1111	0.052*
O3	0.40743 (17)	0.3782 (2)	1.2436 (3)	0.0677 (11)
H3	0.403 (2)	0.340 (5)	1.304 (6)	0.088*
C4	0.42764 (17)	0.2672 (3)	1.0982 (4)	0.0402 (9)
H4A	0.4602	0.3007	1.1111	0.048*
H4B	0.4352	0.2211	1.1713	0.048*
N5	0.40969 (14)	0.2207 (2)	0.9563 (3)	0.0347 (7)
H5	0.3788 (18)	0.247 (3)	0.912 (5)	0.042*
C5A	0.40187 (18)	0.1166 (3)	0.9613 (4)	0.0467 (10)
C5B	0.3601 (2)	0.0995 (3)	1.0265 (5)	0.0565 (12)
H5BA	0.3275	0.1279	0.9704	0.085*
H5BB	0.3716	0.1248	1.1195	0.085*
H5BC	0.3548	0.0348	1.0313	0.085*
C5C	0.4536 (3)	0.0716 (4)	1.0476 (8)	0.088 (2)
H5CA	0.4484	0.0067	1.0504	0.132*
H5CB	0.4653	0.0957	1.1414	0.132*
H5CC	0.4799	0.0837	1.0057	0.132*
C5D	0.3810 (3)	0.0810 (4)	0.8107 (6)	0.087 (2)
H5DA	0.3479	0.1102	0.7601	0.131*
H5DB	0.3758	0.0161	0.8114	0.131*
H5DC	0.4063	0.0943	0.7658	0.131*
C6	0.44360 (18)	0.2516 (3)	0.8723 (5)	0.0455 (10)
H6A	0.4804	0.2354	0.9222	0.055*
H6B	0.4321	0.2206	0.7822	0.055*
C7	0.43895 (16)	0.3537 (3)	0.8497 (4)	0.0404 (9)
C7A	0.4814 (2)	0.4061 (3)	0.8835 (5)	0.0580 (12)
H7AA	0.4780	0.4683	0.8628	0.070*
H7AB	0.5149	0.3810	0.9280	0.070*
C8	0.38396 (17)	0.3902 (3)	0.7778 (4)	0.0456 (10)
H8A	0.3855	0.4562	0.7698	0.055*
H8B	0.3696	0.3650	0.6837	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0625 (2)	0.0625 (2)	0.04158 (18)	−0.00927 (15)	0.01658 (14)	0.00183 (13)
N1	0.0432 (19)	0.0453 (19)	0.0341 (16)	0.0074 (15)	0.0178 (14)	0.0027 (14)
C1A	0.044 (3)	0.097 (4)	0.049 (2)	0.018 (3)	0.017 (2)	0.014 (3)
C1B	0.052 (3)	0.198 (8)	0.053 (3)	−0.008 (4)	0.004 (3)	−0.016 (4)
C1C	0.084 (4)	0.125 (6)	0.108 (5)	0.055 (4)	0.039 (4)	0.060 (5)
C1D	0.046 (3)	0.140 (6)	0.073 (4)	0.002 (3)	0.027 (3)	0.008 (4)
C2	0.059 (3)	0.038 (2)	0.041 (2)	0.0076 (19)	0.0224 (19)	0.0014 (17)
C3	0.060 (3)	0.037 (2)	0.0328 (18)	0.0007 (19)	0.0167 (19)	−0.0038 (17)
O3	0.123 (3)	0.0428 (19)	0.0362 (16)	−0.0053 (19)	0.0263 (18)	−0.0096 (13)
C4	0.051 (2)	0.036 (2)	0.0278 (17)	−0.0024 (18)	0.0065 (17)	0.0003 (16)
N5	0.0392 (18)	0.0324 (17)	0.0333 (16)	0.0030 (13)	0.0136 (14)	−0.0005 (12)
C5A	0.063 (3)	0.030 (2)	0.052 (2)	−0.0013 (18)	0.026 (2)	−0.0033 (18)
C5B	0.078 (3)	0.044 (3)	0.053 (2)	−0.013 (2)	0.030 (2)	0.000 (2)
C5C	0.085 (4)	0.045 (3)	0.133 (6)	0.023 (3)	0.035 (4)	0.014 (3)
C5D	0.163 (7)	0.054 (3)	0.066 (3)	−0.039 (4)	0.065 (4)	−0.028 (3)
C6	0.050 (2)	0.045 (3)	0.050 (2)	0.0012 (19)	0.027 (2)	0.0018 (19)
C7	0.047 (2)	0.042 (2)	0.0367 (19)	−0.0016 (18)	0.0198 (18)	0.0010 (17)
C7A	0.059 (3)	0.057 (3)	0.062 (3)	−0.015 (2)	0.026 (2)	−0.001 (2)
C8	0.052 (3)	0.048 (3)	0.040 (2)	0.0034 (19)	0.0199 (19)	0.0084 (18)

Geometric parameters (Å, º)

N1—C2	1.491 (5)	N5—C6	1.517 (5)
N1—C8	1.489 (5)	N5—C5A	1.539 (5)
N1—C1A	1.506 (6)	N5—H5	0.89 (5)
C1A—C1D	1.523 (7)	C5A—C5B	1.508 (6)
C1A—C1B	1.533 (8)	C5A—C5C	1.513 (7)
C1A—C1C	1.533 (9)	C5A—C5D	1.526 (6)
C1B—H1BA	0.9600	C5B—H5BA	0.9600
C1B—H1BB	0.9600	C5B—H5BB	0.9600
C1B—H1BC	0.9600	C5B—H5BC	0.9600
C1C—H1CA	0.9600	C5C—H5CA	0.9600
C1C—H1CB	0.9600	C5C—H5CB	0.9600
C1C—H1CC	0.9600	C5C—H5CC	0.9600
C1D—H1DA	0.9600	C5D—H5DA	0.9600
C1D—H1DB	0.9600	C5D—H5DB	0.9600
C1D—H1DC	0.9600	C5D—H5DC	0.9600
C2—C3	1.522 (6)	C6—C7	1.509 (6)
C2—H2A	0.9700	C6—H6A	0.9700
C2—H2B	0.9700	C6—H6B	0.9700
C3—O3	1.416 (5)	C7—C7A	1.318 (6)
C3—C4	1.525 (6)	C7—C8	1.500 (6)
C3—H3A	0.9800	C7A—H7AA	0.9300
O3—H3	0.87 (7)	C7A—H7AB	0.9300
C4—N5	1.513 (5)	C8—H8A	0.9700
C4—H4A	0.9700	C8—H8B	0.9700
C4—H4B	0.9700
C2—N1—C8	109.9 (3)	C4—N5—C5A	114.5 (3)
C2—N1—C1A	114.4 (3)	C6—N5—C5A	115.4 (3)
C8—N1—C1A	114.5 (3)	C4—N5—H5	103 (3)
N1—C1A—C1D	108.2 (4)	C6—N5—H5	103 (3)
N1—C1A—C1B	108.1 (4)	C5A—N5—H5	110 (3)
C1D—C1A—C1B	108.4 (5)	C5B—C5A—C5C	110.3 (4)
N1—C1A—C1C	112.0 (5)	C5B—C5A—C5D	108.3 (4)
C1D—C1A—C1C	110.4 (5)	C5C—C5A—C5D	112.0 (5)
C1B—C1A—C1C	109.5 (5)	C5B—C5A—N5	108.1 (3)
C1A—C1B—H1BA	109.5	C5C—C5A—N5	109.9 (4)
C1A—C1B—H1BB	109.5	C5D—C5A—N5	108.1 (3)
H1BA—C1B—H1BB	109.5	C5A—C5B—H5BA	109.5
C1A—C1B—H1BC	109.5	C5A—C5B—H5BB	109.5
H1BA—C1B—H1BC	109.5	H5BA—C5B—H5BB	109.5
H1BB—C1B—H1BC	109.5	C5A—C5B—H5BC	109.5
C1A—C1C—H1CA	109.5	H5BA—C5B—H5BC	109.5
C1A—C1C—H1CB	109.5	H5BB—C5B—H5BC	109.5
H1CA—C1C—H1CB	109.5	C5A—C5C—H5CA	109.5
C1A—C1C—H1CC	109.5	C5A—C5C—H5CB	109.5
H1CA—C1C—H1CC	109.5	H5CA—C5C—H5CB	109.5
H1CB—C1C—H1CC	109.5	C5A—C5C—H5CC	109.5
C1A—C1D—H1DA	109.5	H5CA—C5C—H5CC	109.5
C1A—C1D—H1DB	109.5	H5CB—C5C—H5CC	109.5
H1DA—C1D—H1DB	109.5	C5A—C5D—H5DA	109.5
C1A—C1D—H1DC	109.5	C5A—C5D—H5DB	109.5
H1DA—C1D—H1DC	109.5	H5DA—C5D—H5DB	109.5
H1DB—C1D—H1DC	109.5	C5A—C5D—H5DC	109.5
N1—C2—C3	111.3 (3)	H5DA—C5D—H5DC	109.5
N1—C2—H2A	109.4	H5DB—C5D—H5DC	109.5
C3—C2—H2A	109.4	C7—C6—N5	110.2 (3)
N1—C2—H2B	109.4	C7—C6—H6A	109.6
C3—C2—H2B	109.4	N5—C6—H6A	109.6
H2A—C2—H2B	108.0	C7—C6—H6B	109.6
O3—C3—C2	106.9 (3)	N5—C6—H6B	109.6
O3—C3—C4	108.0 (4)	H6A—C6—H6B	108.1
C2—C3—C4	114.2 (3)	C7A—C7—C8	122.5 (4)
O3—C3—H3A	109.2	C7A—C7—C6	121.1 (4)
C2—C3—H3A	109.2	C8—C7—C6	116.2 (4)
C4—C3—H3A	109.2	C7—C7A—H7AA	120.0
C3—O3—H3	105 (4)	C7—C7A—H7AB	120.0
N5—C4—C3	111.9 (3)	H7AA—C7A—H7AB	120.0
N5—C4—H4A	109.2	N1—C8—C7	111.3 (3)
C3—C4—H4A	109.2	N1—C8—H8A	109.4
N5—C4—H4B	109.2	C7—C8—H8A	109.4
C3—C4—H4B	109.2	N1—C8—H8B	109.4
H4A—C4—H4B	107.9	C7—C8—H8B	109.4
C4—N5—C6	110.3 (3)	H8A—C8—H8B	108.0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···N1	0.89 (5)	1.92 (5)	2.668 (5)	141 (4)
O3—H3···I1	0.87 (7)	2.61 (7)	3.462 (4)	167 (6)