A new polymorph of N-(prop-2-yn­yl)tricyclo­[3.3.1.13,7]decane-1-carbox­amide

Frey, W.; Schetter, S.; Rominger, F.; Hashmi, A.S.K.

doi:10.1107/S1600536808021466

organic compounds

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Volume 64| Part 8| August 2008| Page o1495

doi:10.1107/S1600536808021466

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A new polymorph of N-(prop-2-ynyl)tricyclo[3.3.1.1^3,7]decane-1-carboxamide

Wolfgang Frey,^a Stefanie Schetter,^a Frank Rominger ^b and A. Stephen K. Hashmi ^b ^*

^aInstitut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany, and ^bOrganisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg, 70569 Stuttgart, Germany
^*Correspondence e-mail: hashmi@hashmi.de

(Received 23 June 2008; accepted 10 July 2008; online 16 July 2008)

The alkynyl bond of the title compound, C₁₄H₁₉NO, has a length of 1.170 (5) Å. The amide function shows a trans conformation with respect to the carbonyl group characterized by the torsion angle O—C—N—H of −176 (2)°. There is an intermolecular N—H⋯O hydrogen bond between the amide function and the carbonyl group. In addition, weak intermolecular hydrogen bonds stabilize the crystal structure. A comparison with a polymorphic structure shows conformational differences with regard to the orientation of the carbonyl groups with respect to the adamantyl group [O—C—C—C = 96.2 (3)° in the title compound and 123.7 (2)° in the polymorph] and the orientations of the propargyl groups in relation to the carbonyl groups [O—C—C—C = −87.7 (3) and −58.7 (2)°, respectively].

Related literature

For the monoclinic polymorph, see: Hashmi et al. (2004 ). For gold catalysis research, see: Hashmi (2003 , 2004 , 2005 , 2007 ); Hashmi & Hutchings (2006 ); Hashmi, Frost & Bats (2000 ); Hashmi, Schwarz et al. (2000 ); Hashmi et al. (2006 ). For the synthesis of heterocyclic compounds, see: Milton et al. (2004 ).

Experimental

Crystal data

C₁₄H₁₉NO
M_r = 217.30
Orthorhombic, I b a 2
a = 9.862 (2) Å
b = 28.095 (5) Å
c = 8.664 (3) Å
V = 2400.4 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 (2) K
0.9 × 0.4 × 0.1 mm

Data collection

Nicolet P3 diffractometer
Absorption correction: none
13418 measured reflections
1853 independent reflections
1442 reflections with I > 2σ(I)
R_int = 0.084
3 standard reflections every 50 reflections intensity decay: 2%

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.130
S = 1.09
1853 reflections
150 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

X1 is the midpoint of the alkynyl bond.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.86 (3)	2.16 (4)	2.984 (4)	161 (3)
C1—H1⋯O1ⁱⁱ	0.93	2.41	3.188 (5)	141
C10—H10B⋯O1ⁱ	0.97	2.57	3.515 (4)	164
C3—H3A⋯X1ⁱⁱⁱ	0.97	2.93	3.833	157
C3—H3B⋯X1^iv	0.97	2.93	3.813	151
C6—H6A⋯X1^v	0.97	2.81	3.689	151
Symmetry codes: (i) $[-x, y, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x, y, z-{\script{1\over 2}}]$ ; (v) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: P3/PC Software (Siemens, 1991 ); cell refinement: P3/PC Software; data reduction: XDISK in SHELXTL-Plus (Sheldrick, 2008 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus; software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021466/bt2731sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808021466/bt2731Isup2.hkl

checkCIF report

Comment top

Initiated by our early work on gold-catalyzed additions of nucleophiles to allenes (Hashmi et al., 2000a; Hashmi et al., 2000b) and alkynes (Hashmi & Frost et al., 2000) the investigation of the synthetic potential of propargylic carboxamides in gold-catalyzed reactions (Hashmi, 2007) revealed that they can be excellent precursors for the formation of oxazoles (Hashmi, Weyrauch, Frey & Bats, 2004) and alkylidene oxazolines (Hashmi & Rudolph et al., 2006) in highly selective reactions under mild conditions. As one of the substrates with bulky, sterically demanding substiutents which documented the broad scope of the reaction, the title compound was prepared.

The title compound (Fig. 1) crystallizes with one molecule in the asymmetric unit of the space group Iba2. The alkynyl bond was clearly identified by the distance of 1.170 (5) Å between the carbon atoms C1 and C2. As expected, the N1—H1A amide function shows a trans conformation concerning to the carbonyl group C4=O1 indicated by the torsion angle O1—C4—N1—H1A of -176 (2)°. The crystal packing (Fig. 4) is stabilized by a number of intermolecular hydrogen bond contacts (Fig. 2). A strong intermolecular hydrogen bond works between the amide function N1—H1A as donor and the oxygen O1 of the carbonyl group as acceptor with a H1A···O1 distance of 2.16 Å and an angle N1—H1A···O1 of 161°. The oxygen O1 of the carbonyl function is also an acceptor in more weak interactions, where the alkynyl moiety C1—H1 and the methylen group C10—H10B of the adamantyl system works as donors. The H1···O1 distance is 2.41 Å and the H10B···O1 distance is 2.57 Å respectively. The center of the alkynyl bond X1 works also as acceptor of weak hydrogen bond interactions, where the methylen group of the propargyl moiety C3—H3A and C3—H3B are the donors. The distances of H3A···X1 and H3B···X1 are both 2.93 Å. X1 is also the acceptor of an weak interaction including the methylen group C6—H6A of the adamantyl moiety with a distance H6A···X1 of 2.81 Å (see Table). Hashmi & Weyrauch et al., 2004, reported about a polymorphic structure (further abbreviated as Mol.A) of the title compound crystallized in space group C2/c, which was also crystallized by slow diffusion of petrol ether into a solution of dichloromethane. To get more insight of structural differences the carbon atoms of the adamantyl moieties of both structures were superimposed yielded in an optimal fit with a weighted r.m.s. of 0.0061 Å (Fig. 3, bold bonds shows title compound). The orientations of the carbonyl functions C4=O1 in relation to the adamantyl moiety are quite different characterized by the torsion angle O1—C4—C5—C6 of 96.2 (3)° and 123.7 (2)° (Mol.A). The orientations of the propargyl groups in relation to the carbonyl functions differs also significant indicated by the Newman projection along the carbons C3 and C4 with torsion angles O1—C4—C3—C2 of -87.7 (3)° and -58.7 (2)° (Mol.A) respectively.

Related literature top

For a polymorph, see: Hashmi et al. (2004). For gold catalysis research, see: Hashmi (2003, 2004, 2005a,b, 2007); Hashmi & Hutchings (2006a,b); Hashmi et al. (2000, 2000a,b, 2006). For the synthesis of heterocyclic compounds, see: Milton et al. (2004). X1 is the midpoint of the alkynyl bond.

Experimental top

The title compound was prepared by the reaction of adamantane-1-carboxylic acid chloride with propargyl amine in dichloromethane at 0–20 °C using a 2 mol% of 4-N,N-dimethylaminopyridine as a catalyst in 76% yield as described previously (Hashmi, Weyrauch, Frey & Bats, 2004). Crystals were grown by slow diffusion of petrol ether into a solution of dichloromethane.

Computing details top

Data collection: P3/PC Software (Siemens, 1991); cell refinement: P3/PC Software (Siemens, 1991); data reduction: XDISK in SHELXTL-Plus (Sheldrick, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. Perspective view of the title compound with atom numbering. Displacement ellipsoids are at the 50% probability level.
	Fig. 2. Detailed view of the intermolecular hydrogen bond interactions. (X1A - X1D are the centers of the alkynyl bond)
	Fig. 3. Superposition plot of the title compound (bold bonds) and the formerly reported polymorphic structure (Mol. A, open bonds). For better insight plot without Hydrogen atoms.
	Fig. 4. Cell Plot of the title compound (bc-view, inclusive hydrogen atoms)

N-(prop-2-ynyl)tricyclo[3.3.1.1^3,7]decane-1-carboxamide top

Crystal data top

C₁₄H₁₉NO	F(000) = 944
M_r = 217.30	D_x = 1.203 Mg m⁻³
Orthorhombic, Iba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: I 2 -2c	Cell parameters from 32 reflections
a = 9.862 (2) Å	θ = 9–13°
b = 28.095 (5) Å	µ = 0.08 mm⁻¹
c = 8.664 (3) Å	T = 293 K
V = 2400.4 (10) Å³	Plates, colourless
Z = 8	0.9 × 0.4 × 0.1 mm

Data collection top

Nicolet P3 diffractometer	R_int = 0.084
Radiation source: fine-focus sealed tube	θ_max = 30.0°, θ_min = 2.2°
Graphite monochromator	h = −13→13
Wyckoff ccan scans	k = −39→39
13418 measured reflections	l = −12→12
1853 independent reflections	3 standard reflections every 50 reflections
1442 reflections with I > 2σ(I)	intensity decay: 2%

Refinement top

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)] = 0.061	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.130	w = 1/[σ²(F_o²) + (0.0432P)² + 1.5609P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
1853 reflections	Δρ_max = 0.21 e Å⁻³
150 parameters	Δρ_min = −0.14 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0008 (7)

Crystal data top

C₁₄H₁₉NO	V = 2400.4 (10) Å³
M_r = 217.30	Z = 8
Orthorhombic, Iba2	Mo Kα radiation
a = 9.862 (2) Å	µ = 0.08 mm⁻¹
b = 28.095 (5) Å	T = 293 K
c = 8.664 (3) Å	0.9 × 0.4 × 0.1 mm

Data collection top

Nicolet P3 diffractometer	R_int = 0.084
13418 measured reflections	3 standard reflections every 50 reflections
1853 independent reflections	intensity decay: 2%
1442 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.061	1 restraint
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.21 e Å⁻³
1853 reflections	Δρ_min = −0.14 e Å⁻³
150 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.1418 (2)	0.17494 (8)	0.6152 (3)	0.0516 (6)
N1	0.0006 (3)	0.18653 (8)	0.8136 (3)	0.0417 (5)
H1A	−0.023 (3)	0.1792 (9)	0.906 (4)	0.030 (8)*
C1	0.1177 (4)	0.29834 (13)	0.8851 (6)	0.0648 (11)
H1	0.1746	0.3204	0.9322	0.078*
C2	0.0462 (3)	0.27061 (10)	0.8258 (5)	0.0471 (7)
C3	−0.0418 (3)	0.23362 (9)	0.7609 (4)	0.0466 (7)
H3A	−0.1348	0.2394	0.7923	0.056*
H3B	−0.0380	0.2349	0.6491	0.056*
C4	0.1019 (3)	0.16321 (9)	0.7436 (3)	0.0362 (6)
C5	0.1706 (2)	0.12334 (9)	0.8342 (3)	0.0321 (5)
C6	0.2719 (3)	0.14739 (9)	0.9446 (4)	0.0408 (7)
H6A	0.3346	0.1669	0.8858	0.049*
H6B	0.2233	0.1680	1.0155	0.049*
C7	0.3511 (3)	0.10992 (10)	1.0360 (4)	0.0454 (7)
H7	0.4157	0.1258	1.1049	0.055*
C8	0.2518 (3)	0.08042 (11)	1.1315 (4)	0.0464 (7)
H8A	0.3010	0.0570	1.1916	0.056*
H8B	0.2028	0.1009	1.2021	0.056*
C9	0.1523 (3)	0.05549 (9)	1.0236 (4)	0.0441 (7)
H9	0.0889	0.0363	1.0847	0.053*
C10	0.0723 (3)	0.09276 (9)	0.9302 (4)	0.0413 (6)
H10A	0.0087	0.0768	0.8622	0.050*
H10B	0.0213	0.1130	0.9999	0.050*
C11	0.2495 (3)	0.09040 (11)	0.7245 (4)	0.0482 (8)
H11A	0.1868	0.0748	0.6546	0.058*
H11B	0.3124	0.1091	0.6633	0.058*
C12	0.3275 (3)	0.05301 (11)	0.8169 (4)	0.0524 (8)
H12	0.3773	0.0323	0.7458	0.063*
C13	0.2292 (3)	0.02307 (10)	0.9121 (5)	0.0527 (8)
H13A	0.2788	−0.0009	0.9696	0.063*
H13B	0.1657	0.0070	0.8443	0.063*
C14	0.4276 (3)	0.07773 (12)	0.9248 (5)	0.0538 (8)
H14A	0.4784	0.0541	0.9824	0.065*
H14B	0.4913	0.0965	0.8649	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0513 (12)	0.0591 (13)	0.0445 (12)	0.0059 (10)	0.0039 (11)	0.0162 (11)
N1	0.0433 (12)	0.0404 (11)	0.0415 (14)	0.0062 (11)	0.0031 (12)	0.0088 (12)
C1	0.0506 (17)	0.0527 (18)	0.091 (3)	0.0030 (16)	−0.006 (2)	−0.008 (2)
C2	0.0398 (14)	0.0402 (14)	0.061 (2)	0.0096 (12)	0.0003 (16)	0.0059 (15)
C3	0.0440 (15)	0.0423 (14)	0.0533 (19)	0.0089 (12)	−0.0061 (15)	0.0083 (14)
C4	0.0355 (13)	0.0356 (12)	0.0376 (15)	−0.0056 (10)	−0.0048 (12)	0.0012 (12)
C5	0.0320 (12)	0.0327 (12)	0.0316 (14)	−0.0013 (9)	0.0006 (11)	0.0011 (11)
C6	0.0393 (14)	0.0337 (12)	0.0495 (18)	−0.0075 (11)	−0.0055 (14)	0.0026 (13)
C7	0.0413 (15)	0.0443 (14)	0.0507 (18)	−0.0048 (12)	−0.0143 (15)	0.0036 (15)
C8	0.0570 (18)	0.0448 (15)	0.0375 (16)	0.0059 (13)	−0.0032 (15)	0.0103 (14)
C9	0.0437 (15)	0.0325 (12)	0.056 (2)	−0.0045 (11)	0.0028 (14)	0.0126 (14)
C10	0.0340 (12)	0.0351 (12)	0.0550 (18)	−0.0039 (10)	0.0027 (14)	0.0066 (14)
C11	0.0561 (18)	0.0492 (17)	0.0393 (18)	0.0108 (14)	0.0026 (15)	−0.0028 (13)
C12	0.0593 (19)	0.0477 (16)	0.050 (2)	0.0201 (14)	0.0100 (17)	−0.0022 (16)
C13	0.0624 (19)	0.0313 (13)	0.065 (2)	0.0051 (13)	−0.0091 (19)	−0.0010 (15)
C14	0.0365 (14)	0.0611 (18)	0.064 (2)	0.0086 (13)	0.0026 (16)	0.0153 (19)

Geometric parameters (Å, º) top

O1—C4	1.225 (4)	C8—C9	1.525 (4)
N1—C4	1.340 (4)	C8—H8A	0.9700
N1—C3	1.461 (3)	C8—H8B	0.9700
N1—H1A	0.86 (3)	C9—C13	1.529 (5)
C1—C2	1.170 (5)	C9—C10	1.541 (4)
C1—H1	0.9300	C9—H9	0.9800
C2—C3	1.466 (4)	C10—H10A	0.9700
C3—H3A	0.9700	C10—H10B	0.9700
C3—H3B	0.9700	C11—C12	1.529 (4)
C4—C5	1.526 (4)	C11—H11A	0.9700
C5—C11	1.538 (4)	C11—H11B	0.9700
C5—C10	1.539 (4)	C12—C13	1.526 (5)
C5—C6	1.540 (4)	C12—C14	1.527 (5)
C6—C7	1.531 (4)	C12—H12	0.9800
C6—H6A	0.9700	C13—H13A	0.9700
C6—H6B	0.9700	C13—H13B	0.9700
C7—C14	1.521 (5)	C14—H14A	0.9700
C7—C8	1.527 (4)	C14—H14B	0.9700
C7—H7	0.9800

C4—N1—C3	121.0 (3)	H8A—C8—H8B	108.3
C4—N1—H1A	120.7 (19)	C8—C9—C13	110.0 (3)
C3—N1—H1A	115.4 (19)	C8—C9—C10	109.8 (2)
C2—C1—H1	180.0	C13—C9—C10	109.1 (3)
C1—C2—C3	175.9 (4)	C8—C9—H9	109.3
N1—C3—C2	110.7 (2)	C13—C9—H9	109.3
N1—C3—H3A	109.5	C10—C9—H9	109.3
C2—C3—H3A	109.5	C5—C10—C9	109.9 (2)
N1—C3—H3B	109.5	C5—C10—H10A	109.7
C2—C3—H3B	109.5	C9—C10—H10A	109.7
H3A—C3—H3B	108.1	C5—C10—H10B	109.7
O1—C4—N1	121.3 (3)	C9—C10—H10B	109.7
O1—C4—C5	121.5 (3)	H10A—C10—H10B	108.2
N1—C4—C5	117.2 (2)	C12—C11—C5	110.1 (3)
C4—C5—C11	110.4 (2)	C12—C11—H11A	109.6
C4—C5—C10	114.1 (2)	C5—C11—H11A	109.6
C11—C5—C10	108.5 (2)	C12—C11—H11B	109.6
C4—C5—C6	106.6 (2)	C5—C11—H11B	109.6
C11—C5—C6	108.7 (2)	H11A—C11—H11B	108.1
C10—C5—C6	108.5 (2)	C13—C12—C11	110.0 (3)
C7—C6—C5	110.5 (2)	C13—C12—C14	109.3 (3)
C7—C6—H6A	109.5	C11—C12—C14	109.5 (3)
C5—C6—H6A	109.5	C13—C12—H12	109.3
C7—C6—H6B	109.5	C11—C12—H12	109.3
C5—C6—H6B	109.5	C14—C12—H12	109.3
H6A—C6—H6B	108.1	C12—C13—C9	109.1 (2)
C14—C7—C8	109.8 (2)	C12—C13—H13A	109.9
C14—C7—C6	109.5 (3)	C9—C13—H13A	109.9
C8—C7—C6	109.0 (2)	C12—C13—H13B	109.9
C14—C7—H7	109.5	C9—C13—H13B	109.9
C8—C7—H7	109.5	H13A—C13—H13B	108.3
C6—C7—H7	109.5	C7—C14—C12	109.7 (2)
C9—C8—C7	109.3 (3)	C7—C14—H14A	109.7
C9—C8—H8A	109.8	C12—C14—H14A	109.7
C7—C8—H8A	109.8	C7—C14—H14B	109.7
C9—C8—H8B	109.8	C12—C14—H14B	109.7
C7—C8—H8B	109.8	H14A—C14—H14B	108.2

C4—N1—C3—C2	−82.6 (4)	C8—C9—C10—C5	59.7 (3)
C3—N1—C4—O1	−16.5 (4)	C13—C9—C10—C5	−60.9 (3)
C3—N1—C4—C5	160.2 (3)	C4—C5—C11—C12	175.3 (3)
O1—C4—C5—C11	−21.6 (4)	C10—C5—C11—C12	−59.0 (3)
N1—C4—C5—C11	161.8 (3)	C6—C5—C11—C12	58.8 (3)
O1—C4—C5—C10	−144.0 (3)	C5—C11—C12—C13	60.0 (4)
N1—C4—C5—C10	39.4 (3)	C5—C11—C12—C14	−60.2 (3)
O1—C4—C5—C6	96.2 (3)	C11—C12—C13—C9	−60.3 (4)
N1—C4—C5—C6	−80.4 (3)	C14—C12—C13—C9	60.0 (3)
C4—C5—C6—C7	−177.4 (2)	C8—C9—C13—C12	−60.1 (3)
C11—C5—C6—C7	−58.4 (3)	C10—C9—C13—C12	60.4 (3)
C10—C5—C6—C7	59.3 (3)	C8—C7—C14—C12	59.9 (3)
C5—C6—C7—C14	59.4 (3)	C6—C7—C14—C12	−59.8 (3)
C5—C6—C7—C8	−60.8 (3)	C13—C12—C14—C7	−60.2 (3)
C14—C7—C8—C9	−59.3 (3)	C11—C12—C14—C7	60.4 (3)
C6—C7—C8—C9	60.7 (3)	O1—C4—C3—C2	−87.7 (3)
C7—C8—C9—C13	59.5 (3)	C4—N1—C3—C2	−82.6 (4)
C7—C8—C9—C10	−60.5 (3)	O1—C4—N1—H1A	−176 (2)
C4—C5—C10—C9	−176.9 (2)	H1A—N1—C3—C2	78 (2)
C11—C5—C10—C9	59.6 (3)	O1—C4—C5—C6	96.2 (3)
C6—C5—C10—C9	−58.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86 (3)	2.16 (4)	2.984 (4)	161 (3)
C1—H1···O1ⁱⁱ	0.93	2.41	3.188 (5)	141
C10—H10B···O1ⁱ	0.97	2.57	3.515 (4)	164
C3—H3A···X1ⁱⁱⁱ	0.97	2.93	3.833	157
C3—H3B···X1^iv	0.97	2.93	3.813	151
C6—H6A···X1^v	0.97	2.81	3.689	151

Symmetry codes: (i) −x, y, z+1/2; (ii) −x+1/2, −y+1/2, z+1/2; (iii) x−1/2, y+1/2, z+1/2; (iv) −x, y, z−1/2; (v) x+1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₉NO
M_r	217.30
Crystal system, space group	Orthorhombic, Iba2
Temperature (K)	293
a, b, c (Å)	9.862 (2), 28.095 (5), 8.664 (3)
V (Å³)	2400.4 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.9 × 0.4 × 0.1

Data collection
Diffractometer	Nicolet P3 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13418, 1853, 1442
R_int	0.084
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.130, 1.09
No. of reflections	1853
No. of parameters	150
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.14

Computer programs: P3/PC Software (Siemens, 1991), XDISK in SHELXTL-Plus (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), XP in SHELXTL-Plus (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86 (3)	2.16 (4)	2.984 (4)	161 (3)
C1—H1···O1ⁱⁱ	0.93	2.41	3.188 (5)	141.1
C10—H10B···O1ⁱ	0.97	2.57	3.515 (4)	164.3
C3—H3A···X1ⁱⁱⁱ	0.97	2.93	3.833	157
C3—H3B···X1^iv	0.97	2.93	3.813	151
C6—H6A···X1^v	0.97	2.81	3.689	151

Symmetry codes: (i) −x, y, z+1/2; (ii) −x+1/2, −y+1/2, z+1/2; (iii) x−1/2, y+1/2, z+1/2; (iv) −x, y, z−1/2; (v) x+1/2, y+1/2, z+1/2.

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