3,14-Dimethyl-2,6,13,17-tetra­aza­tricyclo­[16.4.0.07,12]docosa­ne–(naphthalen-1-yl)methanol (1/2)

Choi, J.-H.; Subhan, M.A.; Ryoo, K.S.; Ng, S.W.

doi:10.1107/S160053681105272X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o102

doi:10.1107/S160053681105272X

Open

access

3,14-Dimethyl-2,6,13,17-tetraazatricyclo[16.4.0.0^7,12]docosane–(naphthalen-1-yl)methanol (1/2)

Jong-Ha Choi,^a Md Abdus Subhan,^a Keon Sang Ryoo ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Chemistry, Andong National University, Andong 760-749, Republic of Korea, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 7 December 2011; accepted 7 December 2011; online 14 December 2011)

In the title co-crystal, C₂₀H₄₀N₄·2C₁₁H₁₀O, the macrocycle is generated by a crystallographic inversion centre. The N atoms show a pyramidal coordination, and the cyclohexane ring that is fused to the 14-membered C₁₀N₄ ring exists in a chair conformation, whereas the methyl substituent occupies an axial site. The (naphthalen-1-yl)methanol molecule forms an O—H⋯N hydrogen bond to a cyclam N atom. The mean-square-plane passing through the 14-membered ring is approximately coplanar with the naphthalene fused-ring [dihedral angle = 6.6 (1)°].

Related literature

For the synthesis of the cyclam, see: Kang & Jeong (2003 ).

Experimental

Crystal data

C₂₀H₄₀N₄·2C₁₁H₁₀O
M_r = 652.94
Triclinic, $[P \overline 1]$
a = 8.9706 (4) Å
b = 9.4967 (6) Å
c = 10.5580 (5) Å
α = 92.500 (4)°
β = 97.961 (4)°
γ = 96.666 (4)°
V = 883.13 (8) Å³
Z = 1
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.978, T_max = 0.985
6926 measured reflections
3915 independent reflections
2958 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.126
S = 1.00
3915 reflections
229 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.85 (1)	1.94 (1)	2.786 (2)	171 (2)

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681105272X/hg5151sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681105272X/hg5151Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681105272X/hg5151Isup3.cml

checkCIF report

Comment top

We had intended to react the cyclam having 1,2-diaminocyclohexanediamine sub-units, 5,16-dimethyl-2,6,13,17-tetraazatricyclo[14,4,0^1,18,0^7,12]docosane, with an alkyl chloride to form the corresponding ammonium salt; however, under the basic conditions, the 1-chloromethyl-naphthalene component was hydrolyzed to 1-hydroxymethyl-naphthalene, which co-crystallizes with the cyclam (Scheme I, Fig. 1). The cyclam lies on a center-of-inversion, and the nitrogen atoms of the 14-membered C₁₀N₄ ring show pyramidal coordination. However, these are not enaged in any hydrogen-bonding interactions. The cyclohexane rings that are fused to the 14-membered ring exist in chair conformations, and the methyl substituents in axial configurations.

The 1-hydroxymethyl-naphthalene molecule forms an O–H···N hydrogen bond to the cyclam (Table 1).

The mean-square-plane passing through the 14-membered ring is approximately co-planar with the naphthalene fused-ring (dihedral angle 6.6 (1) °).

Related literature top

For the synthesis of the cyclam, see: Kang & Jeong (2003).

Experimental top

The macrocycle 3,14-dimethyl-2,6,13,17-tetraazatricyclo[16.4.0.0^7,12]docosane was synthesized by using a published procedure (Kang & Jeong, 2003). To a solution of this marcrocycle (0.61 g, 2.0 mmol) in methanol (10 ml) was added 1-chloromethylnaphthalene (0.80 g, 4.53 mmol) and a solution containing sodium carbonate (0.51 g, 4.77 mmol) dissolved in water (5 ml). The solution was heated for 24 h at 363 K. The white solid that precipitated was collected and recrystallized from acetonitrile–water (1:1) solution to give colorless crystals.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₀H₄₀N₄^.2C₁₁H₁₀O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

3,14-Dimethyl-2,6,13,17-tetraazatricyclo[16.4.0.0^7,12]docosane– (naphthalen-1-yl)methanol (1/2) top

Crystal data top

C₂₀H₄₀N₄·2C₁₁H₁₀O	Z = 1
M_r = 652.94	F(000) = 356
Triclinic, P1	D_x = 1.228 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9706 (4) Å	Cell parameters from 2968 reflections
b = 9.4967 (6) Å	θ = 2.8–29.3°
c = 10.5580 (5) Å	µ = 0.08 mm⁻¹
α = 92.500 (4)°	T = 100 K
β = 97.961 (4)°	Prism, colorless
γ = 96.666 (4)°	0.30 × 0.25 × 0.20 mm
V = 883.13 (8) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3915 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2958 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.027
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.8°
ω scan	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −12→9
T_min = 0.978, T_max = 0.985	l = −12→13
6926 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0516P)² + 0.3587P] where P = (F_o² + 2F_c²)/3
3915 reflections	(Δ/σ)_max = 0.001
229 parameters	Δρ_max = 0.29 e Å⁻³
3 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₀H₄₀N₄·2C₁₁H₁₀O	γ = 96.666 (4)°
M_r = 652.94	V = 883.13 (8) Å³
Triclinic, P1	Z = 1
a = 8.9706 (4) Å	Mo Kα radiation
b = 9.4967 (6) Å	µ = 0.08 mm⁻¹
c = 10.5580 (5) Å	T = 100 K
α = 92.500 (4)°	0.30 × 0.25 × 0.20 mm
β = 97.961 (4)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3915 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2958 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.985	R_int = 0.027
6926 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	3 restraints
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.29 e Å⁻³
3915 reflections	Δρ_min = −0.28 e Å⁻³
229 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.39115 (13)	0.38946 (12)	0.62565 (11)	0.0246 (3)
N1	0.10202 (14)	0.30725 (14)	0.49130 (12)	0.0167 (3)
N2	0.02690 (14)	0.51309 (13)	0.31361 (12)	0.0169 (3)
C1	0.04567 (17)	0.24648 (16)	0.70859 (14)	0.0187 (3)
H1A	0.1503	0.2922	0.7383	0.022*
H1B	0.0293	0.1613	0.7582	0.022*
C2	0.03614 (18)	0.19676 (16)	0.56804 (14)	0.0195 (3)
H2A	0.0903	0.1121	0.5622	0.023*
H2B	−0.0715	0.1684	0.5318	0.023*
C3	0.07600 (16)	0.26812 (16)	0.35267 (14)	0.0165 (3)
H3	−0.0335	0.2310	0.3268	0.020*
C4	0.17260 (18)	0.15236 (17)	0.32043 (15)	0.0218 (3)
H4A	0.2808	0.1862	0.3509	0.026*
H4B	0.1442	0.0668	0.3663	0.026*
C5	0.1525 (2)	0.11239 (18)	0.17690 (16)	0.0274 (4)
H5A	0.2219	0.0422	0.1601	0.033*
H5B	0.0473	0.0678	0.1481	0.033*
C6	0.18552 (19)	0.24225 (18)	0.10128 (15)	0.0238 (4)
H6A	0.1632	0.2150	0.0084	0.029*
H6B	0.2943	0.2797	0.1216	0.029*
C7	0.08938 (17)	0.35713 (17)	0.13392 (14)	0.0191 (3)
H7A	−0.0191	0.3223	0.1059	0.023*
H7B	0.1155	0.4420	0.0865	0.023*
C8	0.11388 (16)	0.39903 (16)	0.27810 (14)	0.0161 (3)
H8	0.2240	0.4336	0.3040	0.019*
C9	0.06375 (17)	0.65060 (16)	0.25732 (14)	0.0178 (3)
H9	0.0493	0.6339	0.1620	0.021*
C10	0.22827 (17)	0.71117 (17)	0.30174 (16)	0.0237 (4)
H10A	0.2950	0.6423	0.2792	0.036*
H10B	0.2441	0.7308	0.3948	0.036*
H10C	0.2516	0.7994	0.2598	0.036*
C11	0.40299 (19)	0.53897 (17)	0.62006 (16)	0.0249 (4)
H11A	0.3248	0.5626	0.5512	0.030*
H11B	0.5035	0.5735	0.5968	0.030*
C12	0.38426 (16)	0.61640 (17)	0.74368 (15)	0.0201 (3)
C13	0.36862 (17)	0.54546 (18)	0.85219 (15)	0.0220 (3)
H13	0.3698	0.4455	0.8498	0.026*
C14	0.35081 (18)	0.61807 (19)	0.96724 (16)	0.0256 (4)
H14	0.3424	0.5668	1.0417	0.031*
C15	0.34556 (18)	0.76033 (19)	0.97311 (16)	0.0257 (4)
H15	0.3314	0.8074	1.0510	0.031*
C16	0.36112 (17)	0.83948 (17)	0.86337 (15)	0.0217 (3)
C17	0.35874 (19)	0.98840 (19)	0.86739 (17)	0.0276 (4)
H17	0.3427	1.0366	0.9442	0.033*
C18	0.37914 (18)	1.06392 (19)	0.76259 (17)	0.0291 (4)
H18	0.3779	1.1639	0.7669	0.035*
C19	0.40194 (18)	0.99358 (18)	0.64866 (16)	0.0264 (4)
H19	0.4160	1.0463	0.5759	0.032*
C20	0.40408 (17)	0.84951 (18)	0.64119 (15)	0.0230 (4)
H20	0.4200	0.8038	0.5632	0.028*
C21	0.38299 (16)	0.76716 (17)	0.74774 (15)	0.0195 (3)
H1O	0.3056 (15)	0.356 (2)	0.5834 (18)	0.047 (6)*
H1N	0.0599 (18)	0.3847 (13)	0.5061 (17)	0.027 (5)*
H2N	−0.0694 (12)	0.4833 (19)	0.2849 (16)	0.028 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0249 (6)	0.0183 (6)	0.0294 (7)	0.0014 (5)	0.0008 (5)	0.0018 (5)
N1	0.0221 (6)	0.0120 (6)	0.0163 (6)	0.0029 (5)	0.0030 (5)	0.0024 (5)
N2	0.0185 (6)	0.0132 (6)	0.0196 (7)	0.0028 (5)	0.0039 (5)	0.0028 (5)
C1	0.0247 (8)	0.0156 (8)	0.0165 (8)	0.0044 (6)	0.0027 (6)	0.0052 (6)
C2	0.0259 (8)	0.0125 (7)	0.0207 (8)	0.0022 (6)	0.0053 (6)	0.0023 (6)
C3	0.0194 (7)	0.0143 (7)	0.0158 (7)	0.0014 (6)	0.0030 (5)	0.0009 (6)
C4	0.0312 (8)	0.0166 (8)	0.0200 (8)	0.0076 (7)	0.0069 (6)	0.0041 (6)
C5	0.0440 (10)	0.0179 (8)	0.0232 (9)	0.0087 (7)	0.0108 (7)	0.0011 (7)
C6	0.0338 (9)	0.0210 (8)	0.0192 (8)	0.0080 (7)	0.0085 (7)	0.0024 (6)
C7	0.0226 (8)	0.0180 (8)	0.0172 (8)	0.0031 (6)	0.0040 (6)	0.0030 (6)
C8	0.0176 (7)	0.0134 (7)	0.0177 (8)	0.0031 (6)	0.0032 (5)	0.0016 (6)
C9	0.0247 (8)	0.0145 (7)	0.0151 (7)	0.0035 (6)	0.0038 (6)	0.0039 (6)
C10	0.0258 (8)	0.0174 (8)	0.0288 (9)	0.0025 (6)	0.0063 (7)	0.0047 (7)
C11	0.0306 (9)	0.0184 (8)	0.0245 (9)	−0.0028 (7)	0.0042 (7)	0.0013 (7)
C12	0.0142 (7)	0.0213 (8)	0.0233 (8)	−0.0010 (6)	0.0000 (6)	0.0016 (6)
C13	0.0194 (8)	0.0211 (8)	0.0242 (8)	−0.0001 (6)	0.0001 (6)	0.0047 (6)
C14	0.0229 (8)	0.0310 (10)	0.0224 (9)	−0.0009 (7)	0.0026 (6)	0.0079 (7)
C15	0.0246 (8)	0.0323 (10)	0.0211 (9)	0.0039 (7)	0.0058 (6)	0.0016 (7)
C16	0.0168 (7)	0.0243 (9)	0.0248 (9)	0.0058 (6)	0.0025 (6)	0.0020 (7)
C17	0.0276 (9)	0.0258 (9)	0.0310 (9)	0.0097 (7)	0.0051 (7)	−0.0012 (7)
C18	0.0266 (9)	0.0209 (9)	0.0400 (11)	0.0090 (7)	0.0002 (7)	0.0032 (8)
C19	0.0246 (8)	0.0253 (9)	0.0287 (9)	0.0034 (7)	−0.0004 (7)	0.0087 (7)
C20	0.0211 (8)	0.0241 (9)	0.0227 (8)	0.0009 (7)	0.0006 (6)	0.0018 (7)
C21	0.0142 (7)	0.0208 (8)	0.0227 (8)	0.0016 (6)	−0.0004 (6)	0.0027 (6)

Geometric parameters (Å, º) top

O1—C11	1.4159 (19)	C8—H8	1.0000
O1—H1O	0.852 (9)	C9—C10	1.522 (2)
N1—C2	1.4730 (19)	C9—C1ⁱ	1.529 (2)
N1—C3	1.4739 (19)	C9—H9	1.0000
N1—H1N	0.883 (9)	C10—H10A	0.9800
N2—C8	1.4712 (19)	C10—H10B	0.9800
N2—C9	1.4798 (19)	C10—H10C	0.9800
N2—H2N	0.884 (9)	C11—C12	1.509 (2)
C1—C2	1.525 (2)	C11—H11A	0.9900
C1—C9ⁱ	1.529 (2)	C11—H11B	0.9900
C1—H1A	0.9900	C12—C13	1.370 (2)
C1—H1B	0.9900	C12—C21	1.432 (2)
C2—H2A	0.9900	C13—C14	1.408 (2)
C2—H2B	0.9900	C13—H13	0.9500
C3—C8	1.531 (2)	C14—C15	1.356 (2)
C3—C4	1.531 (2)	C14—H14	0.9500
C3—H3	1.0000	C15—C16	1.422 (2)
C4—C5	1.527 (2)	C15—H15	0.9500
C4—H4A	0.9900	C16—C17	1.416 (2)
C4—H4B	0.9900	C16—C21	1.423 (2)
C5—C6	1.521 (2)	C17—C18	1.366 (3)
C5—H5A	0.9900	C17—H17	0.9500
C5—H5B	0.9900	C18—C19	1.402 (2)
C6—C7	1.523 (2)	C18—H18	0.9500
C6—H6A	0.9900	C19—C20	1.369 (2)
C6—H6B	0.9900	C19—H19	0.9500
C7—C8	1.536 (2)	C20—C21	1.419 (2)
C7—H7A	0.9900	C20—H20	0.9500
C7—H7B	0.9900

C11—O1—H1O	107.1 (15)	N2—C8—H8	107.7
C2—N1—C3	113.32 (11)	C3—C8—H8	107.7
C2—N1—H1N	107.1 (12)	C7—C8—H8	107.7
C3—N1—H1N	109.4 (12)	N2—C9—C10	110.88 (13)
C8—N2—C9	115.46 (11)	N2—C9—C1ⁱ	109.54 (12)
C8—N2—H2N	106.5 (12)	C10—C9—C1ⁱ	111.64 (13)
C9—N2—H2N	106.9 (12)	N2—C9—H9	108.2
C2—C1—C9ⁱ	117.65 (13)	C10—C9—H9	108.2
C2—C1—H1A	107.9	C1ⁱ—C9—H9	108.2
C9ⁱ—C1—H1A	107.9	C9—C10—H10A	109.5
C2—C1—H1B	107.9	C9—C10—H10B	109.5
C9ⁱ—C1—H1B	107.9	H10A—C10—H10B	109.5
H1A—C1—H1B	107.2	C9—C10—H10C	109.5
N1—C2—C1	112.57 (12)	H10A—C10—H10C	109.5
N1—C2—H2A	109.1	H10B—C10—H10C	109.5
C1—C2—H2A	109.1	O1—C11—C12	113.97 (13)
N1—C2—H2B	109.1	O1—C11—H11A	108.8
C1—C2—H2B	109.1	C12—C11—H11A	108.8
H2A—C2—H2B	107.8	O1—C11—H11B	108.8
N1—C3—C8	109.94 (11)	C12—C11—H11B	108.8
N1—C3—C4	110.78 (13)	H11A—C11—H11B	107.7
C8—C3—C4	109.82 (12)	C13—C12—C21	119.27 (15)
N1—C3—H3	108.8	C13—C12—C11	121.36 (15)
C8—C3—H3	108.8	C21—C12—C11	119.36 (14)
C4—C3—H3	108.8	C12—C13—C14	121.18 (16)
C5—C4—C3	112.30 (14)	C12—C13—H13	119.4
C5—C4—H4A	109.1	C14—C13—H13	119.4
C3—C4—H4A	109.1	C15—C14—C13	120.84 (16)
C5—C4—H4B	109.1	C15—C14—H14	119.6
C3—C4—H4B	109.1	C13—C14—H14	119.6
H4A—C4—H4B	107.9	C14—C15—C16	120.42 (15)
C6—C5—C4	111.15 (13)	C14—C15—H15	119.8
C6—C5—H5A	109.4	C16—C15—H15	119.8
C4—C5—H5A	109.4	C17—C16—C15	121.61 (15)
C6—C5—H5B	109.4	C17—C16—C21	119.41 (15)
C4—C5—H5B	109.4	C15—C16—C21	118.96 (15)
H5A—C5—H5B	108.0	C18—C17—C16	121.05 (16)
C5—C6—C7	110.49 (13)	C18—C17—H17	119.5
C5—C6—H6A	109.6	C16—C17—H17	119.5
C7—C6—H6A	109.6	C17—C18—C19	119.87 (16)
C5—C6—H6B	109.6	C17—C18—H18	120.1
C7—C6—H6B	109.6	C19—C18—H18	120.1
H6A—C6—H6B	108.1	C20—C19—C18	120.63 (16)
C6—C7—C8	111.94 (13)	C20—C19—H19	119.7
C6—C7—H7A	109.2	C18—C19—H19	119.7
C8—C7—H7A	109.2	C19—C20—C21	121.27 (15)
C6—C7—H7B	109.2	C19—C20—H20	119.4
C8—C7—H7B	109.2	C21—C20—H20	119.4
H7A—C7—H7B	107.9	C20—C21—C16	117.77 (15)
N2—C8—C3	110.00 (11)	C20—C21—C12	122.93 (14)
N2—C8—C7	113.85 (13)	C16—C21—C12	119.29 (15)
C3—C8—C7	109.72 (12)

C3—N1—C2—C1	−172.40 (12)	C21—C12—C13—C14	0.2 (2)
C9ⁱ—C1—C2—N1	74.70 (17)	C11—C12—C13—C14	−179.85 (14)
C2—N1—C3—C8	166.81 (12)	C12—C13—C14—C15	1.3 (2)
C2—N1—C3—C4	−71.62 (16)	C13—C14—C15—C16	−1.3 (2)
N1—C3—C4—C5	−178.15 (12)	C14—C15—C16—C17	−178.88 (15)
C8—C3—C4—C5	−56.50 (16)	C14—C15—C16—C21	−0.3 (2)
C3—C4—C5—C6	55.34 (18)	C15—C16—C17—C18	177.67 (15)
C4—C5—C6—C7	−54.34 (19)	C21—C16—C17—C18	−0.9 (2)
C5—C6—C7—C8	56.62 (17)	C16—C17—C18—C19	0.4 (2)
C9—N2—C8—C3	174.49 (11)	C17—C18—C19—C20	0.0 (2)
C9—N2—C8—C7	−61.91 (16)	C18—C19—C20—C21	0.2 (2)
N1—C3—C8—N2	−55.05 (15)	C19—C20—C21—C16	−0.7 (2)
C4—C3—C8—N2	−177.19 (12)	C19—C20—C21—C12	179.92 (14)
N1—C3—C8—C7	178.97 (11)	C17—C16—C21—C20	1.0 (2)
C4—C3—C8—C7	56.83 (16)	C15—C16—C21—C20	−177.60 (14)
C6—C7—C8—N2	178.14 (12)	C17—C16—C21—C12	−179.56 (14)
C6—C7—C8—C3	−58.10 (16)	C15—C16—C21—C12	1.8 (2)
C8—N2—C9—C10	−62.00 (16)	C13—C12—C21—C20	177.61 (14)
C8—N2—C9—C1ⁱ	174.34 (12)	C11—C12—C21—C20	−2.3 (2)
O1—C11—C12—C13	4.5 (2)	C13—C12—C21—C16	−1.8 (2)
O1—C11—C12—C21	−175.56 (13)	C11—C12—C21—C16	178.28 (13)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.85 (1)	1.94 (1)	2.786 (2)	171 (2)

Experimental details

Crystal data
Chemical formula	C₂₀H₄₀N₄·2C₁₁H₁₀O
M_r	652.94
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.9706 (4), 9.4967 (6), 10.5580 (5)
α, β, γ (°)	92.500 (4), 97.961 (4), 96.666 (4)
V (Å³)	883.13 (8)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.978, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	6926, 3915, 2958
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.126, 1.00
No. of reflections	3915
No. of parameters	229
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.28

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.85 (1)	1.94 (1)	2.786 (2)	171 (2)

Acknowledgements

We thank Andong National University and the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Kang, S. G. & Jeong, J. H. (2003). Bull. Kor. Chem. Soc, 24, 393–396. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o102

doi:10.1107/S160053681105272X

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3,14-Di­methyl-2,6,13,17-tetra­aza­tri­cyclo­[16.4.0.07,12]docosa­ne–(naphthalen-1-yl)methanol (1/2)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3,14-Dimethyl-2,6,13,17-tetraazatricyclo[16.4.0.0^7,12]docosane–(naphthalen-1-yl)methanol (1/2)