N-(2-Hydroxy-ethyl)-N-(tricyclo-[3.3.1.1]dec-2-yl)benzamide.

The title adamantane derivative, C(19)H(25)NO(2), was synthesized as part of a study into potential anti-tuberculosis agents. The adamantane skeleton displays shorter than normal C-C bond lengths ranging between 1.5230 (15) and 1.5329 (16) Å. The structure displays O-H⋯O hydrogen bonding and an inter-digitated layered packing structure with distinct hydro-philic and hydro-phobic regions.

Related literature

For related literature, see: Bogatcheva et al. (2006 ▶); Jacobson et al. (1987 ▶); Lee et al., (2003 ▶)

Experimental

Crystal data

C19H25NO2

M = 299.40

Monoclinic,

a = 11.4248 (3) Å

b = 16.0902 (4) Å

c = 8.7211 (2) Å

β = 107.9030 (10)°

V = 1525.55 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 173 (2) K

0.44 × 0.33 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: none

19272 measured reflections

3684 independent reflections

2861 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.109

S = 1.12

3684 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: Mercury (Macrae et al., 2006 ▶) and WinGX (Farrugia, 1999 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808013469/fl2199sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013469/fl2199Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H25NO2	F000 = 648
Mr = 299.40	Dx = 1.304 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5317 reflections
a = 11.4248 (3) Å	θ = 2.3–28.2º
b = 16.0902 (4) Å	µ = 0.08 mm−1
c = 8.7211 (2) Å	T = 173 (2) K
β = 107.9030 (10)º	Block, colourless
V = 1525.55 (7) Å3	0.44 × 0.33 × 0.16 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2861 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.050
Monochromator: graphite	θmax = 28.0º
T = 173(2) K	θmin = 1.9º
φ and ω scans	h = −15→15
Absorption correction: none	k = −21→21
19272 measured reflections	l = −11→11
3684 independent reflections

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.0562P)2] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max = 0.001
3684 reflections	Δρmax = 0.29 e Å−3
200 parameters	Δρmin = −0.22 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
C1	0.26872 (10)	0.12522 (7)	0.22178 (13)	0.0191 (2)
H1	0.2797	0.1396	0.3369	0.023*
C2	0.32356 (10)	0.03827 (6)	0.21268 (13)	0.0170 (2)
H2	0.4145	0.0414	0.2656	0.020*
C3	0.30029 (10)	0.01726 (7)	0.03325 (13)	0.0179 (2)
H3	0.3322	−0.0398	0.0239	0.021*
C4	0.16309 (10)	0.02106 (7)	−0.06201 (14)	0.0215 (3)
H4A	0.1512	0.0068	−0.1762	0.026*
H4B	0.1172	−0.0198	−0.0177	0.026*
C5	0.11394 (11)	0.10846 (7)	−0.05095 (14)	0.0226 (3)
H5	0.0244	0.1109	−0.1128	0.027*
C6	0.18444 (11)	0.17132 (7)	−0.12046 (14)	0.0250 (3)
H6A	0.1522	0.2279	−0.1143	0.030*
H6B	0.1728	0.1583	−0.2352	0.030*
C7	0.32164 (11)	0.16808 (7)	−0.02533 (14)	0.0220 (3)
H7	0.3678	0.2092	−0.0707	0.026*
C8	0.33836 (11)	0.18828 (7)	0.15074 (14)	0.0212 (3)
H8A	0.3071	0.2449	0.1592	0.025*
H8B	0.4269	0.1869	0.2126	0.025*
C9	0.13223 (11)	0.12772 (7)	0.12635 (14)	0.0225 (3)
H9A	0.0986	0.1835	0.1362	0.027*
H9B	0.0872	0.0864	0.1709	0.027*
C10	0.36964 (10)	0.08045 (7)	−0.03724 (13)	0.0210 (3)
H10A	0.4586	0.0778	0.0223	0.025*
H10B	0.3586	0.0668	−0.1515	0.025*
C11	0.27216 (11)	−0.11302 (7)	0.24168 (14)	0.0206 (3)
H11A	0.2282	−0.1153	0.1246	0.025*
H11B	0.2266	−0.1482	0.2972	0.025*
C12	0.40094 (11)	−0.14766 (7)	0.27306 (14)	0.0242 (3)
H12A	0.3964	−0.2032	0.2226	0.029*
H12B	0.4490	−0.1107	0.2243	0.029*
C13	0.29089 (10)	−0.01541 (7)	0.45859 (13)	0.0206 (3)
C14	0.22837 (11)	−0.07451 (7)	0.54113 (13)	0.0206 (2)
C15	0.10237 (11)	−0.08725 (8)	0.48552 (15)	0.0264 (3)
H15	0.0542	−0.0607	0.3896	0.032*
C16	0.04662 (12)	−0.13882 (9)	0.56983 (16)	0.0316 (3)
H16	−0.0399	−0.1468	0.5324	0.038*
C17	0.11626 (12)	−0.17845 (8)	0.70758 (15)	0.0299 (3)
H17	0.0780	−0.2149	0.7635	0.036*
C18	0.24153 (12)	−0.16534 (7)	0.76451 (15)	0.0270 (3)
H18	0.2895	−0.1923	0.8601	0.032*
C19	0.29721 (11)	−0.11306 (7)	0.68239 (14)	0.0231 (3)
H19	0.3833	−0.1034	0.7229	0.028*
N1	0.27326 (8)	−0.02630 (5)	0.29804 (11)	0.0183 (2)
O1	0.46035 (8)	−0.15413 (6)	0.44118 (10)	0.0311 (2)
H1A	0.5219	−0.1226	0.4676	0.047*
O2	0.34988 (8)	0.04282 (5)	0.53714 (10)	0.0301 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0225 (6)	0.0194 (5)	0.0167 (5)	−0.0003 (4)	0.0081 (5)	−0.0023 (4)
C2	0.0180 (5)	0.0183 (5)	0.0157 (5)	−0.0021 (4)	0.0064 (4)	0.0004 (4)
C3	0.0201 (6)	0.0183 (5)	0.0166 (5)	−0.0001 (4)	0.0075 (4)	−0.0018 (4)
C4	0.0212 (6)	0.0250 (6)	0.0177 (6)	−0.0035 (5)	0.0052 (5)	−0.0039 (4)
C5	0.0161 (6)	0.0281 (6)	0.0217 (6)	0.0016 (5)	0.0030 (5)	−0.0006 (5)
C6	0.0282 (7)	0.0261 (6)	0.0199 (6)	0.0028 (5)	0.0060 (5)	0.0034 (5)
C7	0.0244 (6)	0.0218 (6)	0.0214 (6)	−0.0014 (5)	0.0094 (5)	0.0032 (5)
C8	0.0235 (6)	0.0186 (5)	0.0218 (6)	−0.0019 (5)	0.0071 (5)	−0.0007 (4)
C9	0.0208 (6)	0.0240 (6)	0.0248 (6)	0.0013 (5)	0.0102 (5)	−0.0015 (5)
C10	0.0193 (6)	0.0269 (6)	0.0183 (6)	−0.0003 (5)	0.0082 (5)	0.0000 (5)
C11	0.0237 (6)	0.0178 (5)	0.0220 (6)	−0.0031 (4)	0.0094 (5)	−0.0016 (4)
C12	0.0251 (6)	0.0211 (6)	0.0282 (7)	0.0004 (5)	0.0109 (5)	0.0004 (5)
C13	0.0208 (6)	0.0225 (6)	0.0182 (6)	−0.0011 (5)	0.0054 (5)	0.0010 (4)
C14	0.0248 (6)	0.0206 (6)	0.0183 (5)	−0.0017 (5)	0.0097 (5)	−0.0022 (4)
C15	0.0242 (6)	0.0327 (7)	0.0222 (6)	−0.0018 (5)	0.0070 (5)	0.0008 (5)
C16	0.0248 (7)	0.0387 (7)	0.0349 (7)	−0.0082 (5)	0.0142 (6)	−0.0039 (6)
C17	0.0386 (8)	0.0254 (6)	0.0340 (7)	−0.0043 (6)	0.0233 (6)	0.0009 (5)
C18	0.0368 (7)	0.0234 (6)	0.0246 (6)	0.0045 (5)	0.0150 (6)	0.0028 (5)
C19	0.0226 (6)	0.0248 (6)	0.0233 (6)	0.0002 (5)	0.0091 (5)	0.0002 (5)
N1	0.0212 (5)	0.0171 (5)	0.0178 (5)	−0.0024 (4)	0.0078 (4)	−0.0006 (4)
O1	0.0250 (5)	0.0372 (5)	0.0302 (5)	0.0001 (4)	0.0070 (4)	0.0092 (4)
O2	0.0386 (5)	0.0317 (5)	0.0189 (4)	−0.0140 (4)	0.0072 (4)	−0.0028 (4)

C1—C9	1.5258 (15)	C9—H9B	0.9900
C1—C8	1.5329 (16)	C10—H10A	0.9900
C1—C2	1.5450 (15)	C10—H10B	0.9900
C1—H1	1.0000	C11—N1	1.4783 (14)
C2—N1	1.4922 (14)	C11—C12	1.5174 (16)
C2—C3	1.5420 (15)	C11—H11A	0.9900
C2—H2	1.0000	C11—H11B	0.9900
C3—C10	1.5293 (15)	C12—O1	1.4175 (14)
C3—C4	1.5330 (15)	C12—H12A	0.9900
C3—H3	1.0000	C12—H12B	0.9900
C4—C5	1.5283 (16)	C13—O2	1.2319 (13)
C4—H4A	0.9900	C13—N1	1.3632 (14)
C4—H4B	0.9900	C13—C14	1.4996 (16)
C5—C9	1.5270 (16)	C14—C15	1.3858 (16)
C5—C6	1.5295 (17)	C14—C19	1.3876 (16)
C5—H5	1.0000	C15—C16	1.3867 (18)
C6—C7	1.5325 (16)	C15—H15	0.9500
C6—H6A	0.9900	C16—C17	1.3766 (19)
C6—H6B	0.9900	C16—H16	0.9500
C7—C8	1.5230 (15)	C17—C18	1.3793 (18)
C7—C10	1.5280 (16)	C17—H17	0.9500
C7—H7	1.0000	C18—C19	1.3804 (16)
C8—H8A	0.9900	C18—H18	0.9500
C8—H8B	0.9900	C19—H19	0.9500
C9—H9A	0.9900	O1—H1A	0.8400
C9—C1—C8	109.43 (9)	C1—C9—H9A	109.6
C9—C1—C2	111.00 (9)	C5—C9—H9A	109.6
C8—C1—C2	108.03 (9)	C1—C9—H9B	109.6
C9—C1—H1	109.5	C5—C9—H9B	109.6
C8—C1—H1	109.5	H9A—C9—H9B	108.1
C2—C1—H1	109.5	C7—C10—C3	110.19 (9)
N1—C2—C3	112.39 (9)	C7—C10—H10A	109.6
N1—C2—C1	112.35 (9)	C3—C10—H10A	109.6
C3—C2—C1	107.73 (9)	C7—C10—H10B	109.6
N1—C2—H2	108.1	C3—C10—H10B	109.6
C3—C2—H2	108.1	H10A—C10—H10B	108.1
C1—C2—H2	108.1	N1—C11—C12	112.21 (9)
C10—C3—C4	108.99 (9)	N1—C11—H11A	109.2
C10—C3—C2	108.25 (9)	C12—C11—H11A	109.2
C4—C3—C2	111.70 (9)	N1—C11—H11B	109.2
C10—C3—H3	109.3	C12—C11—H11B	109.2
C4—C3—H3	109.3	H11A—C11—H11B	107.9
C2—C3—H3	109.3	O1—C12—C11	110.06 (10)
C5—C4—C3	109.69 (9)	O1—C12—H12A	109.6
C5—C4—H4A	109.7	C11—C12—H12A	109.6
C3—C4—H4A	109.7	O1—C12—H12B	109.6
C5—C4—H4B	109.7	C11—C12—H12B	109.6
C3—C4—H4B	109.7	H12A—C12—H12B	108.2
H4A—C4—H4B	108.2	O2—C13—N1	123.49 (10)
C9—C5—C4	108.18 (9)	O2—C13—C14	118.37 (10)
C9—C5—C6	110.02 (10)	N1—C13—C14	118.02 (10)
C4—C5—C6	109.57 (10)	C15—C14—C19	119.26 (11)
C9—C5—H5	109.7	C15—C14—C13	121.52 (10)
C4—C5—H5	109.7	C19—C14—C13	119.08 (10)
C6—C5—H5	109.7	C14—C15—C16	120.01 (12)
C5—C6—C7	109.79 (9)	C14—C15—H15	120.0
C5—C6—H6A	109.7	C16—C15—H15	120.0
C7—C6—H6A	109.7	C17—C16—C15	120.22 (12)
C5—C6—H6B	109.7	C17—C16—H16	119.9
C7—C6—H6B	109.7	C15—C16—H16	119.9
H6A—C6—H6B	108.2	C16—C17—C18	120.05 (12)
C8—C7—C10	109.21 (9)	C16—C17—H17	120.0
C8—C7—C6	109.21 (10)	C18—C17—H17	120.0
C10—C7—C6	108.86 (9)	C17—C18—C19	119.94 (12)
C8—C7—H7	109.8	C17—C18—H18	120.0
C10—C7—H7	109.8	C19—C18—H18	120.0
C6—C7—H7	109.8	C18—C19—C14	120.48 (11)
C7—C8—C1	110.27 (9)	C18—C19—H19	119.8
C7—C8—H8A	109.6	C14—C19—H19	119.8
C1—C8—H8A	109.6	C13—N1—C11	116.51 (9)
C7—C8—H8B	109.6	C13—N1—C2	117.71 (9)
C1—C8—H8B	109.6	C11—N1—C2	117.16 (9)
H8A—C8—H8B	108.1	C12—O1—H1A	109.5
C1—C9—C5	110.23 (9)
C9—C1—C2—N1	−67.42 (12)	C4—C3—C10—C7	60.22 (11)
C8—C1—C2—N1	172.61 (9)	C2—C3—C10—C7	−61.46 (11)
C9—C1—C2—C3	56.91 (12)	N1—C11—C12—O1	65.78 (12)
C8—C1—C2—C3	−63.06 (11)	O2—C13—C14—C15	121.39 (13)
N1—C2—C3—C10	−172.53 (9)	N1—C13—C14—C15	−54.82 (15)
C1—C2—C3—C10	63.16 (11)	O2—C13—C14—C19	−54.31 (15)
N1—C2—C3—C4	67.48 (11)	N1—C13—C14—C19	129.49 (11)
C1—C2—C3—C4	−56.83 (11)	C19—C14—C15—C16	−0.74 (18)
C10—C3—C4—C5	−59.62 (12)	C13—C14—C15—C16	−176.43 (11)
C2—C3—C4—C5	59.94 (12)	C14—C15—C16—C17	−0.94 (19)
C3—C4—C5—C9	−60.20 (12)	C15—C16—C17—C18	1.6 (2)
C3—C4—C5—C6	59.75 (12)	C16—C17—C18—C19	−0.61 (19)
C9—C5—C6—C7	58.95 (12)	C17—C18—C19—C14	−1.08 (18)
C4—C5—C6—C7	−59.87 (12)	C15—C14—C19—C18	1.75 (17)
C5—C6—C7—C8	−59.44 (12)	C13—C14—C19—C18	177.55 (11)
C5—C6—C7—C10	59.72 (12)	O2—C13—N1—C11	144.02 (12)
C10—C7—C8—C1	−59.05 (12)	C14—C13—N1—C11	−39.99 (14)
C6—C7—C8—C1	59.90 (12)	O2—C13—N1—C2	−2.93 (16)
C9—C1—C8—C7	−59.43 (12)	C14—C13—N1—C2	173.06 (9)
C2—C1—C8—C7	61.54 (11)	C12—C11—N1—C13	−80.57 (12)
C8—C1—C9—C5	58.41 (12)	C12—C11—N1—C2	66.57 (12)
C2—C1—C9—C5	−60.73 (12)	C3—C2—N1—C13	178.49 (9)
C4—C5—C9—C1	61.06 (12)	C1—C2—N1—C13	−59.80 (13)
C6—C5—C9—C1	−58.61 (12)	C3—C2—N1—C11	31.75 (13)
C8—C7—C10—C3	58.96 (12)	C1—C2—N1—C11	153.46 (9)
C6—C7—C10—C3	−60.20 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2i	0.84	1.96	2.7735 (12)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2i	0.84	1.96	2.7735 (12)	164

Symmetry code: (i) .