Crystal structure of ethyl (2S)-9-meth­oxy-2-methyl-4-oxo-3,4,5,6-tetra­hydro-2H- 2,6-methano­benzo[g][1,3,5]oxa­diazocine-11-carboxyl­ate

Dhandapani, A.; Manivarman, S.; Subashchandrabose, S.; Gunasekaran, B.

doi:10.1107/S2056989015000559

organic compounds

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ISSN: 2056-9890

Volume 71| Part 2| February 2015| Pages o117-o118

doi:10.1107/S2056989015000559

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Crystal structure of ethyl (2S)-9-methoxy-2-methyl-4-oxo-3,4,5,6-tetrahydro-2H- 2,6-methanobenzo[g][1,3,5]oxadiazocine-11-carboxylate

A. Dhandapani,^a S. Manivarman,^a S. Subashchandrabose ^b and B. Gunasekaran ^c ^*

^aPost Graduate and Research Department of Chemistry, Government Arts College, C-Mutlur, Chidambaram 608 102, Tamil Nadu, India, ^bCentre for Research & Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India, and ^cDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai 603 203, Tamil Nadu, India
^*Correspondence e-mail: phdguna@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 3 January 2015; accepted 11 January 2015; online 17 January 2015)

In the title compound, C₁₅H₁₈N₂O₅, the methoxyphenyl ring makes a dihedral angle of 84.70 (12)° with the mean plane of the tetrahydropyrimidin-2(1H)-one ring. Both the pyran and tetrahydropyrimidin-2(1H)-one rings have distorted envelope conformations with the carboxylate-substituted C atom as the flap. In the crystal, molecules are linked via pairs of N—H⋯O hydrogen bonds, forming zigzag chains propagating along [010], which enclose R²₂(8) ring motifs. The chains are linked by C—H⋯π interactions, forming a two-dimensional network parallel to (100).

Keywords: crystal structure; hydropyrimidine; oxadiazocine; pyran; hydrogen bonding.

CCDC reference: 1043105

1. Related literature

For the biological activity of dihydropyrimidine derivatives, see: Hurst & Hull (1961 ); Ashok et al. (2007 ); Bahekar & Shinde (2004 ); Mayer et al. (1999 ); Kappe (2000 ); For the crystal structures of two very similar compounds, see: Jing et al. (2009 ); Yar et al. (2014 ; Liu et al. (2014 ).

2. Experimental

2.1. Crystal data

C₁₅H₁₈N₂O₅
M_r = 306.31
Monoclinic, P 2₁
a = 9.6982 (14) Å
b = 7.4802 (12) Å
c = 10.8293 (17) Å
β = 111.252 (5)°
V = 732.2 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 295 K
0.25 × 0.20 × 0.20 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.954, T_max = 0.975
10886 measured reflections
3030 independent reflections
2029 reflections with I > 2σ(I)
R_int = 0.053

2.3. Refinement

R[F² > 2σ(F²)] = 0.071
wR(F²) = 0.175
S = 1.14
3030 reflections
203 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), 1371 Friedel pairs
Absolute structure parameter: 0.01 (4)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.86	2.12	2.962 (5)	168
N2—H2A⋯O2ⁱⁱ	0.86	2.11	2.936 (4)	162
C14—H14B⋯Cg1ⁱⁱⁱ	0.96	2.62	3.570 (6)	171
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008, 2015 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1043105

Crystal structure: contains datablock I. DOI: 10.1107/S2056989015000559/su5057sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015000559/su5057Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015000559/su5057Isup3.cml

checkCIF report

Comment top

Dihydropyrimidine derivatives have recently received great attention because of their wide range of therapeutic and pharmacological properties, such as antiviral (Hurst & Hull, 1961), antitumor, antibacterial and antifungal (Ashok et al., 2007), anti-inflammatory (Bahekar & Shinde, 2004), antihypertensive agents, and neuropeptide Y (NPY) antagonists (Mayer et al., 1999). The natural products containing these heterocyclic moieties have been studied as new leads for AIDS therapies (Kappe, 2000).

The molecular structure of the title compound is illustrated in Fig. 1. The methoxyphenyl ring (C1-C6) makes a dihedral angles of 84.70 (12) ° with the mean plane of the tetrahydropyrimidin-2(1H)-one ring (N1/N2/C7-C10). Both the pyran (O1/C3/C4/C7/C10)and tetrahydropyrimidin-2(1H)-one rings have distorted envelope con formations with atom C10 as the flap.

The geometrical parameters of the title molecule agree well with those reported for two very similar compounds, viz. ethyl 2-methyl-4-oxo-3,4,5,6-tetrahydro-2H-2,6-methanobenzo[g][1,3,5]oxadiazocine-11-carboxylate (Jing et al., 2009; Yar et al., 2014) and methyl 2-methyl-4-oxo-3,4,5,6-tetrahydro-2H-2,6-methanobenzo[g][1,3,5]oxadiazocine-11-carboxylate (Liu et al., 2014)

In the crystal, molecules are linked via pairs of N—H···O hydrogen bonds forming zigzag chains propagating along [010], which enclose R²₂(8) ring motifs (Table 1 and Fig. 2). The chains are linked by C-H···π interactions forming a two-dimensional network parallel to (100).

Related literature top

For the biological activity of dihydropyrimidine derivatives, see: Hurst & Hull (1961); Ashok et al. (2007); Bahekar & Shinde (2004); Mayer et al. (1999); Kappe (2000); For the crystal structures of two very similar compounds, see: Jing et al. (2009); Yar et al. (2014; Liu et al. (2014).

Experimental top

2-hydroxy-4-methoxybenzaldehyde (0.76 g, 5 mmol) and urea (0.9 g, 15 mmol) were added to an ethanolic solution of ethyl acetoacetate (0.65 ml, 5 mmol). To this mixture CeCl₃.7H₂O (0.465 g, 25%) was added slowly with stirring. After the addition was complete the reaction mixture was reflux at 363 K. The reaction mixture was then cooled to room temperature, then poured onto crushed ice water and stirred for 10 min. The solid that separated was filtered under suction, washed with water, and then recrystallized from DMSO giving colourless block-like crystals (yield: 96%; m.p.: 463 K).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008, 2015).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis. Hydrogen bonds are shown as dashed lines (see Table 1 for details).

Ethyl (2S)-9-methoxy-2-methyl-4-oxo-3,4,5,6-tetrahydro-2H- 2,6-methanobenzo[g][1,3,5]oxadiazocine-11-carboxylate top

Crystal data top

C₁₅H₁₈N₂O₅	F(000) = 324
M_r = 306.31	D_x = 1.389 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3030 reflections
a = 9.6982 (14) Å	θ = 2.0–26.8°
b = 7.4802 (12) Å	µ = 0.11 mm⁻¹
c = 10.8293 (17) Å	T = 295 K
β = 111.252 (5)°	Block, colourless
V = 732.2 (2) Å³	0.25 × 0.20 × 0.20 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	3030 independent reflections
Radiation source: fine-focus sealed tube	2029 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
Detector resolution: 0 pixels mm^-1	θ_max = 26.9°, θ_min = 2.0°
ω and ϕ scans	h = −11→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→9
T_min = 0.954, T_max = 0.975	l = −13→13
10886 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.071	w = 1/[σ²(F_o²) + (0.0537P)² + 0.7506P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.175	(Δ/σ)_max < 0.001
S = 1.14	Δρ_max = 0.26 e Å⁻³
3030 reflections	Δρ_min = −0.25 e Å⁻³
203 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008)
1 restraint	Extinction coefficient: 0.031 (8)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1371 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.01 (4)

Crystal data top

C₁₅H₁₈N₂O₅	V = 732.2 (2) Å³
M_r = 306.31	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.6982 (14) Å	µ = 0.11 mm⁻¹
b = 7.4802 (12) Å	T = 295 K
c = 10.8293 (17) Å	0.25 × 0.20 × 0.20 mm
β = 111.252 (5)°

Data collection top

Bruker APEXII CCD diffractometer	3030 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2029 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.975	R_int = 0.053
10886 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	H-atom parameters constrained
wR(F²) = 0.175	Δρ_max = 0.26 e Å⁻³
S = 1.14	Δρ_min = −0.25 e Å⁻³
3030 reflections	Absolute structure: Flack (1983), 1371 Friedel pairs
203 parameters	Absolute structure parameter: 0.01 (4)
1 restraint

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

	x	y	z	U_iso*/U_eq
C1	0.9053 (5)	0.2379 (7)	0.5750 (5)	0.0437 (13)
C2	0.8132 (5)	0.0956 (7)	0.5239 (5)	0.0412 (12)
H2	0.8430	−0.0198	0.5535	0.049*
C3	0.6753 (5)	0.1257 (6)	0.4278 (4)	0.0325 (10)
C4	0.6293 (5)	0.2978 (6)	0.3837 (4)	0.0309 (10)
C5	0.7245 (6)	0.4362 (6)	0.4375 (5)	0.0375 (11)
H5	0.6948	0.5519	0.4085	0.045*
C6	0.8629 (6)	0.4105 (7)	0.5331 (5)	0.0455 (13)
H6	0.9257	0.5066	0.5682	0.055*
C7	0.4765 (5)	0.3254 (6)	0.2807 (4)	0.0299 (10)
H7	0.4353	0.4379	0.2984	0.036*
C8	0.4926 (4)	0.1772 (6)	0.0871 (4)	0.0302 (9)
C9	0.4544 (5)	0.0033 (6)	0.2670 (4)	0.0295 (10)
C10	0.3772 (4)	0.1706 (6)	0.2878 (4)	0.0308 (9)
H10	0.3722	0.1671	0.3765	0.037*
C11	0.2243 (5)	0.2001 (7)	0.1873 (5)	0.0412 (11)
C12	0.0178 (7)	0.3958 (9)	0.1308 (6)	0.0700 (19)
H12A	0.0121	0.3701	0.0413	0.084*
H12B	0.0123	0.5244	0.1396	0.084*
C13	−0.1071 (7)	0.3110 (11)	0.1540 (7)	0.088 (2)
H13A	−0.1119	0.1870	0.1299	0.132*
H13B	−0.1974	0.3693	0.1011	0.132*
H13C	−0.0937	0.3212	0.2460	0.132*
C14	0.3703 (5)	−0.1689 (6)	0.2594 (5)	0.0398 (12)
H14A	0.2826	−0.1685	0.1810	0.060*
H14B	0.3432	−0.1792	0.3361	0.060*
H14C	0.4316	−0.2683	0.2564	0.060*
C15	1.1301 (7)	0.3274 (10)	0.7503 (6)	0.074 (2)
H15A	1.1513	0.4157	0.6953	0.111*
H15B	1.2209	0.2756	0.8085	0.111*
H15C	1.0794	0.3828	0.8017	0.111*
N1	0.4778 (4)	0.3287 (5)	0.1464 (3)	0.0341 (9)
H1	0.4690	0.4288	0.1051	0.041*
N2	0.4908 (4)	0.0226 (4)	0.1509 (3)	0.0326 (9)
H2A	0.5136	−0.0733	0.1187	0.039*
O1	0.5875 (3)	−0.0211 (4)	0.3833 (3)	0.0343 (8)
O2	0.5039 (3)	0.1774 (4)	−0.0236 (3)	0.0383 (8)
O3	0.1709 (4)	0.1240 (6)	0.0862 (4)	0.0817 (15)
O4	0.1593 (4)	0.3304 (6)	0.2256 (4)	0.0650 (12)
O5	1.0392 (4)	0.1917 (6)	0.6693 (4)	0.0682 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.033 (3)	0.059 (3)	0.037 (3)	0.002 (2)	0.010 (2)	−0.003 (2)
C2	0.044 (3)	0.040 (3)	0.039 (3)	0.006 (2)	0.014 (2)	0.003 (2)
C3	0.040 (3)	0.028 (2)	0.031 (2)	−0.001 (2)	0.016 (2)	−0.0004 (18)
C4	0.039 (3)	0.028 (2)	0.028 (2)	0.003 (2)	0.015 (2)	0.0012 (19)
C5	0.046 (3)	0.033 (3)	0.038 (3)	−0.003 (2)	0.020 (2)	0.000 (2)
C6	0.046 (3)	0.044 (3)	0.048 (3)	−0.015 (3)	0.018 (3)	−0.008 (2)
C7	0.042 (3)	0.023 (2)	0.028 (2)	0.000 (2)	0.017 (2)	−0.0006 (18)
C8	0.039 (2)	0.026 (2)	0.029 (2)	0.001 (2)	0.0161 (18)	0.000 (2)
C9	0.037 (2)	0.025 (2)	0.028 (2)	0.000 (2)	0.013 (2)	0.0020 (18)
C10	0.036 (2)	0.031 (2)	0.030 (2)	0.001 (2)	0.0173 (18)	−0.002 (2)
C11	0.042 (3)	0.040 (3)	0.042 (3)	0.002 (2)	0.016 (2)	−0.004 (2)
C12	0.060 (4)	0.077 (4)	0.065 (4)	0.028 (4)	0.014 (3)	0.009 (3)
C13	0.060 (4)	0.084 (5)	0.099 (5)	0.006 (4)	0.003 (4)	0.011 (5)
C14	0.051 (3)	0.030 (2)	0.047 (3)	−0.007 (2)	0.028 (2)	−0.002 (2)
C15	0.057 (4)	0.089 (5)	0.055 (3)	−0.020 (4)	−0.006 (3)	0.004 (4)
N1	0.058 (3)	0.0218 (18)	0.0261 (19)	0.0069 (18)	0.0197 (18)	0.0055 (15)
N2	0.050 (2)	0.0202 (19)	0.036 (2)	0.0038 (17)	0.0244 (19)	0.0013 (15)
O1	0.0418 (18)	0.0264 (16)	0.0315 (16)	0.0019 (14)	0.0092 (14)	0.0033 (13)
O2	0.062 (2)	0.0286 (16)	0.0309 (15)	−0.0006 (17)	0.0244 (14)	0.0015 (14)
O3	0.058 (3)	0.089 (3)	0.071 (3)	0.019 (2)	−0.011 (2)	−0.041 (3)
O4	0.060 (2)	0.074 (3)	0.051 (2)	0.037 (2)	0.0092 (19)	−0.004 (2)
O5	0.044 (2)	0.073 (3)	0.066 (2)	0.007 (2)	−0.0064 (19)	−0.008 (2)

Geometric parameters (Å, º) top

C1—C2	1.371 (7)	C9—C10	1.516 (6)
C1—O5	1.373 (6)	C10—C11	1.504 (6)
C1—C6	1.381 (7)	C10—H10	0.9800
C2—C3	1.383 (6)	C11—O3	1.174 (5)
C2—H2	0.9300	C11—O4	1.308 (6)
C3—O1	1.366 (5)	C12—O4	1.468 (7)
C3—C4	1.389 (6)	C12—C13	1.468 (9)
C4—C5	1.369 (6)	C12—H12A	0.9700
C4—C7	1.511 (6)	C12—H12B	0.9700
C5—C6	1.379 (7)	C13—H13A	0.9600
C5—H5	0.9300	C13—H13B	0.9600
C6—H6	0.9300	C13—H13C	0.9600
C7—N1	1.459 (5)	C14—H14A	0.9600
C7—C10	1.526 (6)	C14—H14B	0.9600
C7—H7	0.9800	C14—H14C	0.9600
C8—O2	1.242 (5)	C15—O5	1.420 (7)
C8—N1	1.336 (5)	C15—H15A	0.9600
C8—N2	1.351 (5)	C15—H15B	0.9600
C9—N2	1.431 (6)	C15—H15C	0.9600
C9—O1	1.452 (5)	N1—H1	0.8600
C9—C14	1.510 (6)	N2—H2A	0.8600

C2—C1—O5	114.0 (5)	C7—C10—H10	109.1
C2—C1—C6	121.3 (4)	O3—C11—O4	123.8 (5)
O5—C1—C6	124.6 (5)	O3—C11—C10	126.1 (4)
C1—C2—C3	119.3 (4)	O4—C11—C10	110.0 (4)
C1—C2—H2	120.4	O4—C12—C13	110.9 (5)
C3—C2—H2	120.4	O4—C12—H12A	109.5
O1—C3—C2	116.3 (4)	C13—C12—H12A	109.5
O1—C3—C4	122.9 (4)	O4—C12—H12B	109.5
C2—C3—C4	120.8 (4)	C13—C12—H12B	109.5
C5—C4—C3	118.1 (4)	H12A—C12—H12B	108.1
C5—C4—C7	122.8 (4)	C12—C13—H13A	109.5
C3—C4—C7	119.1 (4)	C12—C13—H13B	109.5
C4—C5—C6	122.5 (4)	H13A—C13—H13B	109.5
C4—C5—H5	118.8	C12—C13—H13C	109.5
C6—C5—H5	118.8	H13A—C13—H13C	109.5
C5—C6—C1	118.1 (5)	H13B—C13—H13C	109.5
C5—C6—H6	121.0	C9—C14—H14A	109.5
C1—C6—H6	121.0	C9—C14—H14B	109.5
N1—C7—C4	112.2 (4)	H14A—C14—H14B	109.5
N1—C7—C10	107.3 (3)	C9—C14—H14C	109.5
C4—C7—C10	109.1 (3)	H14A—C14—H14C	109.5
N1—C7—H7	109.4	H14B—C14—H14C	109.5
C4—C7—H7	109.4	O5—C15—H15A	109.5
C10—C7—H7	109.4	O5—C15—H15B	109.5
O2—C8—N1	121.7 (4)	H15A—C15—H15B	109.5
O2—C8—N2	121.1 (4)	O5—C15—H15C	109.5
N1—C8—N2	117.2 (3)	H15A—C15—H15C	109.5
N2—C9—O1	110.5 (3)	H15B—C15—H15C	109.5
N2—C9—C14	109.8 (3)	C8—N1—C7	120.4 (4)
O1—C9—C14	103.5 (3)	C8—N1—H1	119.8
N2—C9—C10	109.8 (3)	C7—N1—H1	119.8
O1—C9—C10	107.8 (3)	C8—N2—C9	126.1 (3)
C14—C9—C10	115.2 (4)	C8—N2—H2A	117.0
C11—C10—C9	115.1 (4)	C9—N2—H2A	117.0
C11—C10—C7	109.1 (4)	C3—O1—C9	116.7 (3)
C9—C10—C7	105.3 (3)	C11—O4—C12	117.5 (4)
C11—C10—H10	109.1	C1—O5—C15	119.1 (5)
C9—C10—H10	109.1

O5—C1—C2—C3	−179.8 (4)	N1—C7—C10—C9	64.6 (4)
C6—C1—C2—C3	0.4 (7)	C4—C7—C10—C9	−57.2 (4)
C1—C2—C3—O1	−178.5 (4)	C9—C10—C11—O3	−12.8 (7)
C1—C2—C3—C4	−0.5 (7)	C7—C10—C11—O3	105.3 (6)
O1—C3—C4—C5	178.2 (4)	C9—C10—C11—O4	170.0 (4)
C2—C3—C4—C5	0.4 (6)	C7—C10—C11—O4	−71.9 (5)
O1—C3—C4—C7	−0.9 (6)	O2—C8—N1—C7	−175.1 (4)
C2—C3—C4—C7	−178.7 (4)	N2—C8—N1—C7	6.6 (6)
C3—C4—C5—C6	−0.2 (7)	C4—C7—N1—C8	75.5 (5)
C7—C4—C5—C6	178.9 (4)	C10—C7—N1—C8	−44.2 (5)
C4—C5—C6—C1	0.0 (7)	O2—C8—N2—C9	−169.1 (4)
C2—C1—C6—C5	−0.2 (7)	N1—C8—N2—C9	9.1 (6)
O5—C1—C6—C5	−179.9 (5)	O1—C9—N2—C8	−103.2 (5)
C5—C4—C7—N1	87.0 (5)	C14—C9—N2—C8	143.3 (4)
C3—C4—C7—N1	−94.0 (5)	C10—C9—N2—C8	15.7 (6)
C5—C4—C7—C10	−154.3 (4)	C2—C3—O1—C9	−169.5 (4)
C3—C4—C7—C10	24.7 (5)	C4—C3—O1—C9	12.6 (6)
N2—C9—C10—C11	69.2 (5)	N2—C9—O1—C3	72.7 (4)
O1—C9—C10—C11	−170.3 (3)	C14—C9—O1—C3	−169.9 (4)
C14—C9—C10—C11	−55.3 (5)	C10—C9—O1—C3	−47.4 (5)
N2—C9—C10—C7	−50.9 (4)	O3—C11—O4—C12	−6.2 (8)
O1—C9—C10—C7	69.5 (4)	C10—C11—O4—C12	171.1 (5)
C14—C9—C10—C7	−175.5 (4)	C13—C12—O4—C11	96.3 (7)
N1—C7—C10—C11	−59.5 (4)	C2—C1—O5—C15	−166.0 (5)
C4—C7—C10—C11	178.8 (3)	C6—C1—O5—C15	13.8 (8)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	2.12	2.962 (5)	168
N2—H2A···O2ⁱⁱ	0.86	2.11	2.936 (4)	162
C14—H14B···Cg1ⁱⁱⁱ	0.96	2.62	3.570 (6)	171

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	2.12	2.962 (5)	168
N2—H2A···O2ⁱⁱ	0.86	2.11	2.936 (4)	162
C14—H14B···Cg1ⁱⁱⁱ	0.96	2.62	3.570 (6)	171

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

References

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Volume 71| Part 2| February 2015| Pages o117-o118

doi:10.1107/S2056989015000559

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

Crystal structure of ethyl (2S)-9-meth­­oxy-2-methyl-4-oxo-3,4,5,6-tetra­hydro-2H- 2,6-methano­benzo[g][1,3,5]oxa­diazocine-11-carboxyl­ate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

References

organic compounds

Crystal structure of ethyl (2S)-9-methoxy-2-methyl-4-oxo-3,4,5,6-tetrahydro-2H- 2,6-methanobenzo[g][1,3,5]oxadiazocine-11-carboxylate