N-p-Tolyladamantane-1-carboxamide

SiMa, W.

doi:10.1107/S1600536809036101

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2452

doi:10.1107/S1600536809036101

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N-p-Tolyladamantane-1-carboxamide

Weiwei SiMa ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: nysima@126.com

(Received 1 August 2009; accepted 7 September 2009; online 12 September 2009)

In the crystal of the title compound, C₁₈H₂₃NO, the molecules are linked into chains along the c axis by intermolecular N—H⋯O hydrogen bonds.

Related literature

For For bond-length data, see: Allen et al. (1987 ). For the synthesis of the title compound, see: Karle et al. (1997 ); Tadashi et al. (1969 )

Experimental

Crystal data

C₁₈H₂₃NO
M_r = 269.37
Orthorhombic, P c c n
a = 30.708 (7) Å
b = 9.7927 (2) Å
c = 10.0203 (6) Å
V = 3013.2 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 K
0.50 × 0.30 × 0.30 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.964, T_max = 0.978
27405 measured reflections
3443 independent reflections
2652 reflections with I > 2σ(I)
R_int = 0.080

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.174
S = 1.16
3443 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.12	2.962 (2)	166
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PRPKAPPA (Ferguson, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809036101/er2072sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809036101/er2072Isup2.hkl

checkCIF report

Comment top

The unique structure of adamantane and the pharmaccutical effects of adamantane-containing agents on virus (Davis et al., 1964) have attracted many chemists and pharmacologists to do considerable work on the syntheses of adamantane derivatives (Fort et al., 1964). The crystal structure of the title compound (I) is reported herein.

The molecular structure of compound (I), C₁₈H₂₃ON, is shown in Figure 1. All bond lengths and bond correspond to the geometry parameters expected for atom types and the type of hybridization (Allen et al., 1987). The bonds to nitrogen of the title amide, Fig. 1, the torsion angles of O1—C8—N1—C1 and C9—C8—N1—C1 are 1.70 (3)° and 178.59 (18)°, respectively. The C8—N1 bond has considerable double-bond characer, at 1.349 (2) Å, is substantially shorter than the normal C—N single-bond distance observed in amines. In the crystal of (I), the intermolecular N₁—H···O₁ H-bonds linked molecules to chains along the c axis (Fig.2). And the N₁—H···O₁ bond length is 2.962 (2) Å.

Related literature top

For the the pharmaceutical effects of adamantane-containing agents on viruses, see: Davis et al. (1964). for the synthesis of adamantane derivatives, see: Fort et al. (1964). For bond-length data, see: Allen et al. (1987). For the synthesis of the title compound, see: Karle et al. (1997); Tadashi et al. (1969)

Experimental top

A solution of freshly prepared 1-adamantane carbonyl chloride (1 mmol, prepared by refluxing 1-adamantane carboxylic acid with 3M excess of SOCl₂) in dry CH₂Cl₂ was added dropwise to a well stirred and ice-cooled solution of p-toluidine (1 mmol) and triethylamine (2 mmol) in the same solvent. After 24 h of stirring at room temperature, the solvents were removed in vacuo and the residue was recrystallized from methanol. Colorless single crystals of the title compound suitable for X-ray diffraction analysis were obtained then and the yield was 80% (Isabella et al. 1997; Tadashi et al., 1969).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PRPKAPPA (Ferguson, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound, with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level, and all H atoms have been omitted for clarity.
	Fig. 2. A view of the packing of the title compound, stacking along the b axis. Dashed lines indicate hydrogen bonds.

N-p-Tolyladamantane-1-carboxamide top

Crystal data top

C₁₈H₂₃NO	F(000) = 1168
M_r = 269.37	D_x = 1.188 Mg m⁻³
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 4945 reflections
a = 30.708 (7) Å	θ = 2.5–27.5°
b = 9.7927 (2) Å	µ = 0.07 mm⁻¹
c = 10.0203 (6) Å	T = 298 K
V = 3013.2 (7) Å³	Block, colourless
Z = 8	0.50 × 0.30 × 0.30 mm

Data collection top

Rigaku SCXmini diffractometer	3443 independent reflections
Radiation source: fine-focus sealed tube	2652 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.080
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 2.7°
CCD Profile fitting scans	h = −39→39
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→12
T_min = 0.964, T_max = 0.978	l = −12→12
27405 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.174	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.0692P)² + 0.7031P] where P = (F_o² + 2F_c²)/3
3443 reflections	(Δ/σ)_max = 0.001
182 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₈H₂₃NO	V = 3013.2 (7) Å³
M_r = 269.37	Z = 8
Orthorhombic, Pccn	Mo Kα radiation
a = 30.708 (7) Å	µ = 0.07 mm⁻¹
b = 9.7927 (2) Å	T = 298 K
c = 10.0203 (6) Å	0.50 × 0.30 × 0.30 mm

Data collection top

Rigaku SCXmini diffractometer	3443 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2652 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.978	R_int = 0.080
27405 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.174	H-atom parameters constrained
S = 1.16	Δρ_max = 0.20 e Å⁻³
3443 reflections	Δρ_min = −0.15 e Å⁻³
182 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
C1	0.41659 (6)	0.06223 (19)	−0.01785 (19)	0.0377 (4)
C2	0.41516 (7)	−0.0339 (2)	0.0824 (2)	0.0487 (5)
H2	0.3978	−0.0195	0.1570	0.058*
C3	0.43961 (8)	−0.1518 (2)	0.0718 (2)	0.0531 (6)
H3	0.4382	−0.2159	0.1401	0.064*
C4	0.46586 (7)	−0.1775 (2)	−0.0360 (2)	0.0497 (5)
C5	0.46711 (7)	−0.0805 (2)	−0.1354 (2)	0.0531 (6)
H5	0.4846	−0.0952	−0.2097	0.064*
C6	0.44298 (7)	0.0383 (2)	−0.1273 (2)	0.0485 (5)
H6	0.4445	0.1024	−0.1956	0.058*
C7	0.49221 (9)	−0.3075 (3)	−0.0462 (3)	0.0744 (8)
H7A	0.5182	−0.2903	−0.0967	0.112*
H7B	0.4752	−0.3765	−0.0901	0.112*
H7C	0.4999	−0.3382	0.0417	0.112*
C8	0.37650 (6)	0.2542 (2)	0.08852 (18)	0.0364 (4)
C9	0.34923 (6)	0.38031 (19)	0.05641 (18)	0.0351 (4)
C10	0.33115 (7)	0.4418 (2)	0.1861 (2)	0.0472 (5)
H10A	0.3550	0.4667	0.2446	0.057*
H10B	0.3133	0.3746	0.2317	0.057*
C11	0.30364 (8)	0.5690 (2)	0.1545 (2)	0.0534 (6)
H11	0.2923	0.6076	0.2378	0.064*
C12	0.33198 (9)	0.6739 (2)	0.0850 (3)	0.0618 (7)
H12A	0.3561	0.6990	0.1424	0.074*
H12B	0.3151	0.7555	0.0667	0.074*
C13	0.34927 (8)	0.6146 (2)	−0.0453 (2)	0.0549 (6)
H13	0.3671	0.6831	−0.0910	0.066*
C14	0.37712 (7)	0.4883 (2)	−0.0142 (2)	0.0446 (5)
H14A	0.3888	0.4509	−0.0964	0.053*
H14B	0.4014	0.5140	0.0425	0.053*
C15	0.31066 (7)	0.3420 (2)	−0.0341 (2)	0.0437 (5)
H15A	0.3214	0.3033	−0.1169	0.052*
H15B	0.2928	0.2737	0.0098	0.052*
C16	0.28321 (7)	0.4687 (2)	−0.0641 (2)	0.0535 (6)
H16	0.2587	0.4435	−0.1217	0.064*
C17	0.31163 (8)	0.5726 (3)	−0.1349 (2)	0.0591 (6)
H17A	0.2944	0.6523	−0.1578	0.071*
H17B	0.3229	0.5335	−0.2169	0.071*
C18	0.26607 (8)	0.5283 (3)	0.0655 (3)	0.0599 (6)
H18A	0.2482	0.6076	0.0466	0.072*
H18B	0.2481	0.4612	0.1108	0.072*
N1	0.39146 (6)	0.18381 (17)	−0.01773 (15)	0.0414 (4)
H1	0.3850	0.2166	−0.0948	0.050*
O1	0.38450 (5)	0.21905 (16)	0.20311 (13)	0.0529 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0387 (10)	0.0392 (10)	0.0352 (10)	0.0041 (8)	−0.0014 (8)	−0.0063 (8)
C2	0.0507 (12)	0.0489 (12)	0.0466 (12)	0.0075 (10)	0.0105 (10)	0.0025 (10)
C3	0.0563 (13)	0.0424 (12)	0.0605 (14)	0.0078 (10)	0.0049 (11)	0.0054 (10)
C4	0.0426 (11)	0.0435 (12)	0.0630 (14)	0.0054 (10)	−0.0001 (11)	−0.0114 (10)
C5	0.0505 (12)	0.0568 (14)	0.0521 (13)	0.0072 (11)	0.0102 (10)	−0.0147 (11)
C6	0.0549 (13)	0.0503 (12)	0.0401 (11)	0.0064 (10)	0.0073 (9)	−0.0032 (9)
C7	0.0662 (16)	0.0551 (15)	0.102 (2)	0.0201 (13)	0.0048 (16)	−0.0105 (15)
C8	0.0393 (10)	0.0396 (10)	0.0301 (9)	0.0009 (8)	−0.0011 (8)	−0.0010 (8)
C9	0.0373 (10)	0.0367 (10)	0.0314 (9)	0.0023 (8)	0.0015 (8)	−0.0010 (8)
C10	0.0554 (13)	0.0460 (12)	0.0401 (11)	0.0084 (10)	0.0054 (9)	−0.0034 (9)
C11	0.0580 (13)	0.0476 (13)	0.0546 (13)	0.0119 (11)	0.0107 (11)	−0.0057 (10)
C12	0.0654 (15)	0.0386 (12)	0.0813 (18)	0.0055 (11)	0.0027 (13)	−0.0045 (12)
C13	0.0574 (13)	0.0424 (12)	0.0650 (15)	−0.0040 (10)	0.0069 (12)	0.0133 (11)
C14	0.0436 (11)	0.0420 (11)	0.0480 (11)	−0.0012 (9)	0.0047 (9)	0.0015 (9)
C15	0.0420 (11)	0.0435 (11)	0.0455 (11)	−0.0007 (9)	−0.0027 (9)	−0.0001 (9)
C16	0.0459 (12)	0.0566 (14)	0.0580 (13)	0.0049 (11)	−0.0076 (10)	0.0047 (11)
C17	0.0641 (15)	0.0552 (14)	0.0580 (14)	0.0144 (12)	−0.0006 (12)	0.0184 (12)
C18	0.0455 (12)	0.0543 (14)	0.0799 (17)	0.0116 (11)	0.0081 (12)	0.0055 (13)
N1	0.0521 (10)	0.0437 (9)	0.0284 (8)	0.0141 (8)	0.0000 (7)	0.0007 (7)
O1	0.0778 (11)	0.0511 (9)	0.0297 (7)	0.0213 (8)	−0.0035 (7)	−0.0015 (6)

Geometric parameters (Å, º) top

C1—C2	1.377 (3)	C10—H10B	0.9700
C1—C6	1.383 (3)	C11—C18	1.512 (3)
C1—N1	1.419 (2)	C11—C12	1.516 (3)
C2—C3	1.381 (3)	C11—H11	0.9800
C2—H2	0.9300	C12—C13	1.525 (3)
C3—C4	1.371 (3)	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C5	1.377 (3)	C13—C17	1.520 (3)
C4—C7	1.512 (3)	C13—C14	1.536 (3)
C5—C6	1.382 (3)	C13—H13	0.9800
C5—H5	0.9300	C14—H14A	0.9700
C6—H6	0.9300	C14—H14B	0.9700
C7—H7A	0.9600	C15—C16	1.530 (3)
C7—H7B	0.9600	C15—H15A	0.9700
C7—H7C	0.9600	C15—H15B	0.9700
C8—O1	1.224 (2)	C16—C17	1.517 (3)
C8—N1	1.349 (2)	C16—C18	1.518 (3)
C8—C9	1.526 (3)	C16—H16	0.9800
C9—C14	1.534 (3)	C17—H17A	0.9700
C9—C10	1.536 (3)	C17—H17B	0.9700
C9—C15	1.538 (3)	C18—H18A	0.9700
C10—C11	1.537 (3)	C18—H18B	0.9700
C10—H10A	0.9700	N1—H1	0.8600

C2—C1—C6	118.76 (19)	C11—C12—C13	109.58 (19)
C2—C1—N1	123.74 (17)	C11—C12—H12A	109.8
C6—C1—N1	117.48 (18)	C13—C12—H12A	109.8
C1—C2—C3	119.8 (2)	C11—C12—H12B	109.8
C1—C2—H2	120.1	C13—C12—H12B	109.8
C3—C2—H2	120.1	H12A—C12—H12B	108.2
C4—C3—C2	122.3 (2)	C17—C13—C12	110.1 (2)
C4—C3—H3	118.9	C17—C13—C14	109.01 (19)
C2—C3—H3	118.9	C12—C13—C14	109.09 (19)
C3—C4—C5	117.4 (2)	C17—C13—H13	109.5
C3—C4—C7	121.5 (2)	C12—C13—H13	109.5
C5—C4—C7	121.1 (2)	C14—C13—H13	109.5
C4—C5—C6	121.6 (2)	C9—C14—C13	109.75 (17)
C4—C5—H5	119.2	C9—C14—H14A	109.7
C6—C5—H5	119.2	C13—C14—H14A	109.7
C5—C6—C1	120.2 (2)	C9—C14—H14B	109.7
C5—C6—H6	119.9	C13—C14—H14B	109.7
C1—C6—H6	119.9	H14A—C14—H14B	108.2
C4—C7—H7A	109.5	C16—C15—C9	109.99 (17)
C4—C7—H7B	109.5	C16—C15—H15A	109.7
H7A—C7—H7B	109.5	C9—C15—H15A	109.7
C4—C7—H7C	109.5	C16—C15—H15B	109.7
H7A—C7—H7C	109.5	C9—C15—H15B	109.7
H7B—C7—H7C	109.5	H15A—C15—H15B	108.2
O1—C8—N1	121.90 (18)	C17—C16—C18	110.0 (2)
O1—C8—C9	122.38 (17)	C17—C16—C15	108.61 (18)
N1—C8—C9	115.72 (15)	C18—C16—C15	109.57 (19)
C8—C9—C14	110.41 (15)	C17—C16—H16	109.5
C8—C9—C10	109.71 (15)	C18—C16—H16	109.5
C14—C9—C10	108.77 (16)	C15—C16—H16	109.5
C8—C9—C15	110.43 (16)	C16—C17—C13	110.00 (19)
C14—C9—C15	109.04 (16)	C16—C17—H17A	109.7
C10—C9—C15	108.43 (16)	C13—C17—H17A	109.7
C9—C10—C11	110.01 (17)	C16—C17—H17B	109.7
C9—C10—H10A	109.7	C13—C17—H17B	109.7
C11—C10—H10A	109.7	H17A—C17—H17B	108.2
C9—C10—H10B	109.7	C11—C18—C16	109.94 (19)
C11—C10—H10B	109.7	C11—C18—H18A	109.7
H10A—C10—H10B	108.2	C16—C18—H18A	109.7
C18—C11—C12	110.2 (2)	C11—C18—H18B	109.7
C18—C11—C10	109.11 (18)	C16—C18—H18B	109.7
C12—C11—C10	109.15 (18)	H18A—C18—H18B	108.2
C18—C11—H11	109.4	C8—N1—C1	127.93 (16)
C12—C11—H11	109.4	C8—N1—H1	116.0
C10—C11—H11	109.4	C1—N1—H1	116.0

C6—C1—C2—C3	−0.4 (3)	C11—C12—C13—C14	−61.2 (2)
N1—C1—C2—C3	177.7 (2)	C8—C9—C14—C13	−179.79 (16)
C1—C2—C3—C4	0.3 (4)	C10—C9—C14—C13	−59.4 (2)
C2—C3—C4—C5	−0.1 (4)	C15—C9—C14—C13	58.7 (2)
C2—C3—C4—C7	−179.7 (2)	C17—C13—C14—C9	−59.7 (2)
C3—C4—C5—C6	0.1 (4)	C12—C13—C14—C9	60.5 (2)
C7—C4—C5—C6	179.6 (2)	C8—C9—C15—C16	179.22 (16)
C4—C5—C6—C1	−0.2 (3)	C14—C9—C15—C16	−59.3 (2)
C2—C1—C6—C5	0.4 (3)	C10—C9—C15—C16	59.0 (2)
N1—C1—C6—C5	−177.82 (19)	C9—C15—C16—C17	60.4 (2)
O1—C8—C9—C14	114.5 (2)	C9—C15—C16—C18	−59.8 (2)
N1—C8—C9—C14	−65.3 (2)	C18—C16—C17—C13	58.4 (2)
O1—C8—C9—C10	−5.4 (3)	C15—C16—C17—C13	−61.5 (3)
N1—C8—C9—C10	174.87 (17)	C12—C13—C17—C16	−58.3 (3)
O1—C8—C9—C15	−124.8 (2)	C14—C13—C17—C16	61.3 (2)
N1—C8—C9—C15	55.4 (2)	C12—C11—C18—C16	59.4 (2)
C8—C9—C10—C11	180.00 (17)	C10—C11—C18—C16	−60.5 (2)
C14—C9—C10—C11	59.1 (2)	C17—C16—C18—C11	−58.9 (2)
C15—C9—C10—C11	−59.3 (2)	C15—C16—C18—C11	60.4 (2)
C9—C10—C11—C18	60.4 (2)	O1—C8—N1—C1	1.7 (3)
C9—C10—C11—C12	−60.1 (2)	C9—C8—N1—C1	−178.59 (18)
C18—C11—C12—C13	−59.0 (2)	C2—C1—N1—C8	28.1 (3)
C10—C11—C12—C13	60.8 (3)	C6—C1—N1—C8	−153.8 (2)
C11—C12—C13—C17	58.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.12	2.962 (2)	166

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₃NO
M_r	269.37
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	298
a, b, c (Å)	30.708 (7), 9.7927 (2), 10.0203 (6)
V (Å³)	3013.2 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.50 × 0.30 × 0.30

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.964, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	27405, 3443, 2652
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.174, 1.16
No. of reflections	3443
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.15

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PRPKAPPA (Ferguson, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.12	2.962 (2)	166.0

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

The author is grateful to the starter fund of Southeast University for financial support to buy the X-ray diffractometer.

References

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