(5-Ethenyl-1-aza­bicyclo­[2.2.2]octan-2-yl)(6-meth­oxy-3-quinol­yl)methanol methanol solvate

Muramulla, S.; Arman, H.D.; Zhao, C.-G.; Tiekink, E.R.T.

doi:10.1107/S1600536809045073

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2962

https://doi.org/10.1107/S1600536809045073

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(5-Ethenyl-1-azabicyclo[2.2.2]octan-2-yl)(6-methoxy-3-quinolyl)methanol methanol solvate

Savitha Muramulla,^a Hadi D. Arman,^a Cong-Gui Zhao ^a ‡ and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 27 October 2009; accepted 28 October 2009; online 31 October 2009)

In the title methanol solvate, C₂₀H₂₄N₂O₂·CH₄O, an L-shaped conformation is found as the two substituents at the central hydroxy group are almost orthogonal to each other [the C—C—C angle at the central sp³-C atom is 110.12 (13)°]. The most notable feature of the crystal packing is the formation of supramolecular chains along the b direction mediated by O—H⋯N hydrogen bonds occurring between the hydroxy and quinoline N atoms; the methanol molecules are linked to these chains via O—H⋯N_amine hydrogen bonds. C—H⋯O interactions also occur.

Related literature

For background to pre-catalyst molecules for the Michael addition of acetone to trans-β-nitrostyrene, see: Mandal & Zhao (2008 ).

Experimental

Crystal data

C₂₀H₂₄N₂O₂·CH₄O
M_r = 356.45
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.5374 (13) Å
b = 12.9842 (17) Å
c = 15.871 (2) Å
V = 1965.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 98 K
0.12 × 0.10 × 0.04 mm

Data collection

Rigaku AFC12K/SATURN724 diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.788, T_max = 1.000
14410 measured reflections
2561 independent reflections
2501 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.108
S = 1.08
2561 reflections
243 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3o⋯N1	0.84	1.95	2.783 (2)	171
O1—H1o⋯N2ⁱ	0.84	1.92	2.751 (2)	173
C20—H20b⋯O1ⁱⁱ	0.98	2.33	3.298 (2)	171
C18—H18⋯O3ⁱⁱⁱ	0.95	2.58	3.471 (2)	155
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x+1, y, z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 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: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809045073/hb5191sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809045073/hb5191Isup2.hkl

checkCIF report

Comment top

Molecules related to and including the title compound, (I), have been evaluated as pre-catalysts for the Michael addition of acetone to trans-β-nitrostyrene, see: Mandal & Zhao (2008).

The molecule of (I), Fig. 1, adopts an `L'-shaped conformation whereby the substituted quinoline and dabco residues are linked at the central sp³-C10 atom carrying the hydroxy group, the C1–C10–C11 angle is 110.12 (13)°. Viewed down the N1···C3 axis, the dabco molecule adopts an essentially eclipsed conformation. Both the hydroxy and vinyl groups are orientated towards the same side of the molecule.

In the crystal structure, molecules are connected into a supramolecular chain along the b axis via O—H···N2 hydrogen bonds formed between the O1-hydroxy group and the N2 atom of the quinoline residue, Table 1 and Fig. 2. The lattice methanol molecules associate with this chain via O—H···N1 hydrogen bonds. Chains are consolidated in the crystal packing by C–H···O interactions, Table 1.

Related literature top

For background to pre-catalyst molecules for the Michael addition of acetone to trans-β-nitrostyrene, see: Mandal & Zhao (2008).

Experimental top

Quinidine (TCI America Chemicals) and `L'-proline (Sigma Aldrich) were obtained commercially and used as received. A 1:1 molar ratio of quinidine (100 mg) and `L'-proline (35 mg) were taken in methanol (8 ml) and upon upon vapour diffusion of hexane, colourless crystals formed within 7 days.

Structure description top

Molecules related to and including the title compound, (I), have been evaluated as pre-catalysts for the Michael addition of acetone to trans-β-nitrostyrene, see: Mandal & Zhao (2008).

For background to pre-catalyst molecules for the Michael addition of acetone to trans-β-nitrostyrene, see: Mandal & Zhao (2008).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the asymmetric unit in (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level. The O—H···N hydrogen bond is shown as a dashed line.
	Fig. 2. Supramolecular chain in (I) mediated by O–H···N hydrogen bonds (orange dashed lines). Methanol molecules are associated with this chain via O–H···N hydrogen bonds (black dashed lines).

(5-Ethenyl-1-azabicyclo[2.2.2]octan-2-yl)(6-methoxy-3-quinolyl)methanol methanol solvate top

Crystal data top

C₂₀H₂₄N₂O₂·CH₄O	F(000) = 768
M_r = 356.45	D_x = 1.205 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7299 reflections
a = 9.5374 (13) Å	θ = 2.0–40.2°
b = 12.9842 (17) Å	µ = 0.08 mm⁻¹
c = 15.871 (2) Å	T = 98 K
V = 1965.4 (4) Å³	Platelet, colourless
Z = 4	0.12 × 0.10 × 0.04 mm

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	2561 independent reflections
Radiation source: fine-focus sealed tube	2501 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
T_min = 0.788, T_max = 1.000	k = −16→16
14410 measured reflections	l = −18→20

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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.108	w = 1/[σ²(F_o²) + (0.067P)² + 0.3164P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
2561 reflections	Δρ_max = 0.35 e Å⁻³
243 parameters	Δρ_min = −0.27 e Å⁻³
2 restraints	Absolute structure: nd
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₀H₂₄N₂O₂·CH₄O	V = 1965.4 (4) Å³
M_r = 356.45	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.5374 (13) Å	µ = 0.08 mm⁻¹
b = 12.9842 (17) Å	T = 98 K
c = 15.871 (2) Å	0.12 × 0.10 × 0.04 mm

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	2561 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2501 reflections with I > 2σ(I)
T_min = 0.788, T_max = 1.000	R_int = 0.043
14410 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	2 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.08	Δρ_max = 0.35 e Å⁻³
2561 reflections	Δρ_min = −0.27 e Å⁻³
243 parameters	Absolute structure: nd

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	−0.09211 (13)	0.48893 (9)	0.86000 (8)	0.0208 (3)
H1O	−0.0859	0.5528	0.8526	0.031*
O2	0.56486 (13)	0.36533 (10)	0.77309 (8)	0.0235 (3)
O3	0.32503 (17)	0.60866 (12)	0.92437 (9)	0.0349 (4)
H3O	0.2607	0.5712	0.9435	0.052*
N1	0.12984 (17)	0.48168 (12)	1.00313 (9)	0.0245 (3)
N2	0.05966 (17)	0.19494 (12)	0.67553 (10)	0.0228 (3)
C1	0.08927 (18)	0.39987 (13)	0.94193 (10)	0.0191 (3)
H1	0.1754	0.3580	0.9312	0.023*
C2	−0.0200 (2)	0.32607 (14)	0.98034 (12)	0.0250 (4)
H2A	−0.1135	0.3393	0.9556	0.030*
H2B	0.0061	0.2537	0.9684	0.030*
C3	−0.0236 (2)	0.34482 (17)	1.07595 (13)	0.0299 (4)
H3	−0.0827	0.2913	1.1041	0.036*
C4	0.1270 (2)	0.33999 (17)	1.10976 (13)	0.0324 (5)
H4A	0.1711	0.2738	1.0936	0.039*
H4B	0.1266	0.3449	1.1720	0.039*
C5	0.2101 (2)	0.43074 (17)	1.07174 (13)	0.0304 (4)
H5A	0.2310	0.4816	1.1165	0.036*
H5B	0.3004	0.4051	1.0491	0.036*
C6	0.0053 (2)	0.53057 (16)	1.04185 (12)	0.0327 (5)
H6A	−0.0539	0.5607	0.9970	0.039*
H6B	0.0362	0.5872	1.0792	0.039*
C7	−0.0833 (2)	0.45269 (18)	1.09371 (12)	0.0329 (5)
H7	−0.0694	0.4681	1.1549	0.039*
C8	−0.2379 (3)	0.4605 (2)	1.07452 (16)	0.0498 (7)
H8	−0.2650	0.4626	1.0170	0.060*
C9	−0.3375 (3)	0.4646 (2)	1.13121 (18)	0.0534 (7)
H9A	−0.3145	0.4626	1.1894	0.064*
H9B	−0.4327	0.4695	1.1141	0.064*
C10	0.04468 (16)	0.44563 (13)	0.85620 (11)	0.0175 (3)
H10	0.1126	0.5010	0.8402	0.021*
C11	0.04985 (18)	0.36143 (13)	0.78993 (10)	0.0182 (3)
C12	−0.07008 (19)	0.31535 (14)	0.76062 (12)	0.0227 (4)
H12	−0.1593	0.3392	0.7787	0.027*
C13	−0.06039 (19)	0.23226 (15)	0.70350 (12)	0.0249 (4)
H13	−0.1449	0.2015	0.6842	0.030*
C14	0.18062 (18)	0.24173 (13)	0.70160 (10)	0.0196 (3)
C15	0.18147 (17)	0.32619 (13)	0.75884 (10)	0.0172 (3)
C16	0.31191 (18)	0.37064 (13)	0.78240 (10)	0.0180 (3)
H16	0.3137	0.4283	0.8193	0.022*
C17	0.43522 (18)	0.33065 (13)	0.75211 (11)	0.0191 (3)
C18	0.43402 (19)	0.24588 (14)	0.69502 (11)	0.0213 (3)
H18	0.5199	0.2187	0.6743	0.026*
C19	0.31040 (19)	0.20397 (14)	0.67016 (11)	0.0216 (3)
H19	0.3106	0.1485	0.6311	0.026*
C20	0.57014 (19)	0.44156 (15)	0.83814 (14)	0.0288 (4)
H20A	0.5219	0.5040	0.8191	0.043*
H20B	0.6682	0.4579	0.8510	0.043*
H20C	0.5240	0.4150	0.8888	0.043*
C21	0.3789 (4)	0.6699 (3)	0.98995 (18)	0.0793 (13)
H21A	0.3187	0.7303	0.9979	0.119*
H21B	0.4740	0.6925	0.9755	0.119*
H21C	0.3816	0.6296	1.0421	0.119*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0171 (6)	0.0161 (5)	0.0292 (6)	0.0017 (5)	0.0012 (5)	−0.0008 (5)
O2	0.0157 (5)	0.0233 (6)	0.0314 (6)	−0.0006 (5)	0.0013 (5)	−0.0028 (5)
O3	0.0421 (9)	0.0361 (8)	0.0265 (6)	−0.0121 (7)	0.0075 (6)	−0.0059 (6)
N1	0.0303 (8)	0.0229 (7)	0.0203 (6)	−0.0048 (6)	−0.0025 (6)	−0.0006 (6)
N2	0.0230 (7)	0.0193 (7)	0.0262 (7)	−0.0012 (6)	−0.0012 (6)	−0.0032 (6)
C1	0.0206 (8)	0.0166 (7)	0.0202 (7)	−0.0011 (6)	0.0009 (6)	0.0007 (6)
C2	0.0281 (9)	0.0209 (8)	0.0259 (8)	−0.0048 (7)	0.0028 (7)	0.0031 (7)
C3	0.0292 (9)	0.0362 (11)	0.0242 (8)	−0.0031 (8)	0.0029 (8)	0.0098 (8)
C4	0.0322 (10)	0.0360 (11)	0.0291 (9)	0.0001 (9)	−0.0013 (8)	0.0110 (8)
C5	0.0320 (10)	0.0346 (10)	0.0244 (8)	−0.0049 (8)	−0.0060 (8)	0.0027 (8)
C6	0.0487 (12)	0.0262 (10)	0.0234 (8)	0.0091 (9)	−0.0014 (9)	−0.0047 (8)
C7	0.0318 (10)	0.0468 (12)	0.0201 (8)	0.0083 (10)	0.0039 (8)	−0.0020 (8)
C8	0.0360 (12)	0.080 (2)	0.0335 (11)	0.0157 (13)	−0.0006 (10)	−0.0086 (13)
C9	0.0388 (12)	0.0715 (19)	0.0500 (14)	0.0109 (13)	0.0095 (11)	0.0000 (14)
C10	0.0151 (7)	0.0161 (7)	0.0212 (7)	0.0002 (6)	0.0008 (6)	−0.0003 (6)
C11	0.0189 (7)	0.0155 (7)	0.0201 (7)	−0.0002 (6)	0.0010 (6)	0.0012 (6)
C12	0.0178 (7)	0.0216 (8)	0.0288 (8)	0.0019 (7)	0.0005 (7)	−0.0039 (7)
C13	0.0208 (8)	0.0230 (8)	0.0311 (9)	−0.0020 (7)	−0.0030 (7)	−0.0047 (7)
C14	0.0218 (8)	0.0175 (8)	0.0195 (7)	0.0009 (7)	0.0005 (6)	−0.0014 (6)
C15	0.0181 (7)	0.0151 (7)	0.0184 (7)	0.0002 (6)	0.0003 (6)	0.0009 (6)
C16	0.0190 (7)	0.0163 (7)	0.0186 (7)	−0.0009 (6)	0.0003 (6)	0.0007 (6)
C17	0.0186 (7)	0.0180 (8)	0.0207 (7)	−0.0003 (6)	0.0004 (6)	0.0033 (6)
C18	0.0210 (7)	0.0211 (8)	0.0217 (8)	0.0039 (7)	0.0046 (7)	0.0008 (7)
C19	0.0252 (8)	0.0183 (8)	0.0212 (7)	0.0025 (7)	0.0019 (7)	−0.0023 (6)
C20	0.0171 (7)	0.0270 (9)	0.0422 (10)	−0.0017 (7)	−0.0009 (8)	−0.0092 (8)
C21	0.106 (3)	0.092 (3)	0.0397 (14)	−0.069 (2)	0.0241 (16)	−0.0203 (15)

Geometric parameters (Å, º) top

O1—C10	1.4218 (19)	C7—C8	1.509 (3)
O1—H1O	0.8400	C7—H7	1.0000
O2—C17	1.357 (2)	C8—C9	1.309 (4)
O2—C20	1.431 (2)	C8—H8	0.9500
O3—C21	1.407 (3)	C9—H9A	0.9500
O3—H3O	0.8401	C9—H9B	0.9500
N1—C6	1.480 (3)	C10—C11	1.518 (2)
N1—C5	1.487 (2)	C10—H10	1.0000
N1—C1	1.490 (2)	C11—C12	1.372 (2)
N2—C13	1.320 (2)	C11—C15	1.424 (2)
N2—C14	1.368 (2)	C12—C13	1.412 (2)
C1—C2	1.541 (2)	C12—H12	0.9500
C1—C10	1.544 (2)	C13—H13	0.9500
C1—H1	1.0000	C14—C19	1.422 (2)
C2—C3	1.537 (3)	C14—C15	1.424 (2)
C2—H2A	0.9900	C15—C16	1.421 (2)
C2—H2B	0.9900	C16—C17	1.373 (2)
C3—C4	1.534 (3)	C16—H16	0.9500
C3—C7	1.538 (3)	C17—C18	1.426 (2)
C3—H3	1.0000	C18—C19	1.357 (3)
C4—C5	1.543 (3)	C18—H18	0.9500
C4—H4A	0.9900	C19—H19	0.9500
C4—H4B	0.9900	C20—H20A	0.9800
C5—H5A	0.9900	C20—H20B	0.9800
C5—H5B	0.9900	C20—H20C	0.9800
C6—C7	1.553 (3)	C21—H21A	0.9800
C6—H6A	0.9900	C21—H21B	0.9800
C6—H6B	0.9900	C21—H21C	0.9800

C10—O1—H1O	108.6	C9—C8—H8	117.5
C17—O2—C20	116.01 (13)	C7—C8—H8	117.5
C21—O3—H3O	109.2	C8—C9—H9A	120.0
C6—N1—C5	107.46 (15)	C8—C9—H9B	120.0
C6—N1—C1	111.58 (15)	H9A—C9—H9B	120.0
C5—N1—C1	107.09 (15)	O1—C10—C11	110.12 (13)
C13—N2—C14	117.82 (15)	O1—C10—C1	111.56 (13)
N1—C1—C2	111.16 (14)	C11—C10—C1	108.93 (14)
N1—C1—C10	111.80 (14)	O1—C10—H10	108.7
C2—C1—C10	113.66 (14)	C11—C10—H10	108.7
N1—C1—H1	106.6	C1—C10—H10	108.7
C2—C1—H1	106.6	C12—C11—C15	118.50 (15)
C10—C1—H1	106.6	C12—C11—C10	121.46 (15)
C3—C2—C1	107.88 (15)	C15—C11—C10	120.01 (14)
C3—C2—H2A	110.1	C11—C12—C13	119.75 (16)
C1—C2—H2A	110.1	C11—C12—H12	120.1
C3—C2—H2B	110.1	C13—C12—H12	120.1
C1—C2—H2B	110.1	N2—C13—C12	123.58 (17)
H2A—C2—H2B	108.4	N2—C13—H13	118.2
C4—C3—C2	108.53 (17)	C12—C13—H13	118.2
C4—C3—C7	108.63 (18)	N2—C14—C19	118.35 (15)
C2—C3—C7	109.48 (16)	N2—C14—C15	122.68 (15)
C4—C3—H3	110.1	C19—C14—C15	118.98 (15)
C2—C3—H3	110.1	C16—C15—C14	119.04 (15)
C7—C3—H3	110.1	C16—C15—C11	123.35 (15)
C3—C4—C5	108.25 (16)	C14—C15—C11	117.60 (15)
C3—C4—H4A	110.0	C17—C16—C15	120.28 (15)
C5—C4—H4A	110.0	C17—C16—H16	119.9
C3—C4—H4B	110.0	C15—C16—H16	119.9
C5—C4—H4B	110.0	O2—C17—C16	124.69 (16)
H4A—C4—H4B	108.4	O2—C17—C18	114.79 (15)
N1—C5—C4	111.18 (16)	C16—C17—C18	120.52 (16)
N1—C5—H5A	109.4	C19—C18—C17	120.08 (16)
C4—C5—H5A	109.4	C19—C18—H18	120.0
N1—C5—H5B	109.4	C17—C18—H18	120.0
C4—C5—H5B	109.4	C18—C19—C14	121.07 (16)
H5A—C5—H5B	108.0	C18—C19—H19	119.5
N1—C6—C7	112.16 (16)	C14—C19—H19	119.5
N1—C6—H6A	109.2	O2—C20—H20A	109.5
C7—C6—H6A	109.2	O2—C20—H20B	109.5
N1—C6—H6B	109.2	H20A—C20—H20B	109.5
C7—C6—H6B	109.2	O2—C20—H20C	109.5
H6A—C6—H6B	107.9	H20A—C20—H20C	109.5
C8—C7—C3	112.7 (2)	H20B—C20—H20C	109.5
C8—C7—C6	112.37 (19)	O3—C21—H21A	109.5
C3—C7—C6	107.13 (15)	O3—C21—H21B	109.5
C8—C7—H7	108.2	H21A—C21—H21B	109.5
C3—C7—H7	108.2	O3—C21—H21C	109.5
C6—C7—H7	108.2	H21A—C21—H21C	109.5
C9—C8—C7	124.9 (2)	H21B—C21—H21C	109.5

C6—N1—C1—C2	−48.65 (19)	C1—C10—C11—C12	103.71 (18)
C5—N1—C1—C2	68.68 (19)	O1—C10—C11—C15	163.18 (14)
C6—N1—C1—C10	79.54 (17)	C1—C10—C11—C15	−74.18 (19)
C5—N1—C1—C10	−163.12 (14)	C15—C11—C12—C13	2.5 (3)
N1—C1—C2—C3	−14.0 (2)	C10—C11—C12—C13	−175.43 (16)
C10—C1—C2—C3	−141.20 (16)	C14—N2—C13—C12	−2.0 (3)
C1—C2—C3—C4	−51.1 (2)	C11—C12—C13—N2	−0.1 (3)
C1—C2—C3—C7	67.3 (2)	C13—N2—C14—C19	−178.37 (17)
C2—C3—C4—C5	65.3 (2)	C13—N2—C14—C15	1.8 (3)
C7—C3—C4—C5	−53.6 (2)	N2—C14—C15—C16	−179.73 (16)
C6—N1—C5—C4	66.4 (2)	C19—C14—C15—C16	0.4 (2)
C1—N1—C5—C4	−53.6 (2)	N2—C14—C15—C11	0.6 (2)
C3—C4—C5—N1	−10.8 (2)	C19—C14—C15—C11	−179.29 (15)
C5—N1—C6—C7	−54.7 (2)	C12—C11—C15—C16	177.65 (17)
C1—N1—C6—C7	62.44 (19)	C10—C11—C15—C16	−4.4 (2)
C4—C3—C7—C8	−171.49 (17)	C12—C11—C15—C14	−2.7 (2)
C2—C3—C7—C8	70.1 (2)	C10—C11—C15—C14	175.28 (15)
C4—C3—C7—C6	64.42 (19)	C14—C15—C16—C17	−1.8 (2)
C2—C3—C7—C6	−53.9 (2)	C11—C15—C16—C17	177.88 (16)
N1—C6—C7—C8	−133.14 (19)	C20—O2—C17—C16	6.9 (2)
N1—C6—C7—C3	−8.8 (2)	C20—O2—C17—C18	−172.46 (15)
C3—C7—C8—C9	106.1 (3)	C15—C16—C17—O2	−177.66 (16)
C6—C7—C8—C9	−132.7 (3)	C15—C16—C17—C18	1.6 (2)
N1—C1—C10—O1	−76.08 (17)	O2—C17—C18—C19	179.34 (16)
C2—C1—C10—O1	50.77 (19)	C16—C17—C18—C19	0.0 (3)
N1—C1—C10—C11	162.15 (14)	C17—C18—C19—C14	−1.4 (3)
C2—C1—C10—C11	−71.00 (17)	N2—C14—C19—C18	−178.68 (17)
O1—C10—C11—C12	−18.9 (2)	C15—C14—C19—C18	1.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···N1	0.84	1.95	2.783 (2)	171
O1—H1o···N2ⁱ	0.84	1.92	2.751 (2)	173
C20—H20b···O1ⁱⁱ	0.98	2.33	3.298 (2)	171
C18—H18···O3ⁱⁱⁱ	0.95	2.58	3.471 (2)	155

Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) x+1, y, z; (iii) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₄N₂O₂·CH₄O
M_r	356.45
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	98
a, b, c (Å)	9.5374 (13), 12.9842 (17), 15.871 (2)
V (Å³)	1965.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.12 × 0.10 × 0.04

Data collection
Diffractometer	Rigaku AFC12K/SATURN724
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.788, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14410, 2561, 2501
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.108, 1.08
No. of reflections	2561
No. of parameters	243
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.27
Absolute structure	Nd

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···N1	0.84	1.95	2.783 (2)	171
O1—H1o···N2ⁱ	0.84	1.92	2.751 (2)	173
C20—H20b···O1ⁱⁱ	0.98	2.33	3.298 (2)	171
C18—H18···O3ⁱⁱⁱ	0.95	2.58	3.471 (2)	155

Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) x+1, y, z; (iii) −x+1, y−1/2, −z+3/2.

Footnotes

‡Additional correspondence author, e-mail: cong.zhao@utsa.edu.

Acknowledgements

CGZ thanks the National Science Foundation (grant No. CHE-0909954) for financial support of this project.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Mandal, T. & Zhao, C.-G. (2008). Angew. Chem. Int. Ed. 47, 7714–7717. Web of Science CrossRef CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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