N-(7-Dibromo­methyl-5-methyl-1,8-naphthyridin-2-yl)acetamide–pyrrolidine-2,5-dione (1/1)

Gou, G.-Z.; Kou, J.-F.; Zhou, Q.-D.; Chi, S.-M.

doi:10.1107/S1600536812051112

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Pages o153-o154

doi:10.1107/S1600536812051112

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N-(7-Dibromomethyl-5-methyl-1,8-naphthyridin-2-yl)acetamide–pyrrolidine-2,5-dione (1/1)

Gao-Zhang Gou,^a Jun-Feng Kou,^a Qing-Di Zhou ^b and Shao-Ming Chi ^a ^*

^aCollege of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, People's Republic of China, and ^bSchool of Chemistry, The University of Sydney, Sydney, NSW 2006, Australia
^*Correspondence e-mail: chishaoming@gmail.com

(Received 29 November 2012; accepted 18 December 2012; online 4 January 2013)

In the title co-crystal, C₁₂H₁₁Br₂N₃O·C₄H₅NO₂, the naphthyridine derivative and the pyrrolidine-2,5-dione molecules have crystallographic mirror-plane symmetry with all non-H atoms, except the Br atom, located on the mirror plane. In the crystal, N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds link the molecules into heterodimers. These dimers are further linked into a one-dimensional structure along [010] by weak C—Br⋯O interactions [Br⋯O = 3.028 (5) Å and C—Br⋯O = 158.52 (4)°].

Related literature

For coordination properties of 1,8-naphthyridine ligands, see: Gan et al. (2011 ); Chang et al. (2011 ); Das et al. (2012 ); Li et al. (2011 ). For similar structures, see: Li et al. (2011). For applications of similar compounds, see: Samadi et al. (2011 ); Li et al. (2012 ); Tanaka et al. (2012 ). For information on their synthesis, see: Henry & Hammond (1977 ); Wang et al. (2008 ).

Experimental

Crystal data

C₁₂H₁₁Br₂N₃O·C₄H₅NO₂
M_r = 472.15
Monoclinic, P 2₁ /m
a = 11.537 (2) Å
b = 7.0093 (14) Å
c = 11.632 (2) Å
β = 106.57 (3)°
V = 901.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 4.52 mm⁻¹
T = 293 K
0.21 × 0.19 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.450, T_max = 0.497
7056 measured reflections
1723 independent reflections
1220 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.164
S = 1.12
1723 reflections
148 parameters
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.92 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O1	0.93	2.25	2.838 (10)	121
C9—H9A⋯O3ⁱ	0.98	2.55	3.507 (11)	166
N4—H4A⋯N1ⁱⁱ	0.86	2.56	3.317 (9)	147
N4—H4A⋯N2ⁱⁱ	0.86	2.24	3.045 (8)	157
N3—H3A⋯O2ⁱ	0.86	2.18	3.038 (9)	177
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2006 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg,1999 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812051112/gk2541sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812051112/gk2541Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812051112/gk2541Isup3.cml

checkCIF report

Comment top

Structures and chemical properties of 1,8-naphthyridine derivatives have been investigated owing to their interesting complexation properties, medical uses and chemical applications. They can act as the ligands linking to metals via several coordination modes (Gan et al., 2011; Chang et al., 2011; Das et al., 2012; Li et al., 2011), as drugs (Samadi et al., 2011) and as molecular probe (Li et al., 2012; Tanaka et al., 2012). Herein we report the synthesis and structure of the title co-crystal which was unintentionally obtained during the synthesis of the naphthiridine derivative.

The structure of the title co-crystal is shown in Figs. 1 and 2 and hydrogen-bond geometry is given in Table 1. Both molecules are located on a mirror plane. There are three (N—H···N, N—H···O and C—H···O) intermoleular hydrogen bonds between the crystal components linking the molecules to form heterodimers. The complementarity of hydrogen-bonding interactions stabilizes the dimeric structure, and, most probably, it is the reason why the two components were not easily separated during chromatographic procedure.

Related literature top

For coordination properties of 1,8-naphthyridine ligands, see: Gan et al. (2011); Chang et al. (2011); Das et al. (2012); Li et al. (2011). For similar structures, see: Li et al. (2011). For applications of similar compounds, see: Samadi et al. (2011); Li et al. (2012); Tanaka et al. (2012). For information on their synthesis, see: Henry & Hammond (1977); Wang et al. (2008).

Experimental top

7-Acetylamino-2,4-dimethyl-1,8-naphthyridine (Wang et al., 2008; Henry & Hammond, 1977) (500 mg, 2,32 mmol) and N-bromosuccinimide (0.49 g, 2.79 mmol) were added to an acetonitrile (20 ml) solution in the nitrogen atmosphere. The mixture was stirred at room temperature in the presence of light, a 250 W infrared lamp was used as a light source, for 4 hrs. Excess solvent was removed and the crude product was purified by column chromatography using dichloromethane/methanol (39:1) as the mobile phase to give a white powder. Yield: 250 mg (30%). Crystals suitable for X-ray analysis were obtained by slow diffusion of diethyl ether into the solution of the powder in dichloromethane. To remove succinimide from the sample several cycles of purification by column chromatography had to be carried out. The pure white brominated naphthyridine compound was characterized by ¹H NMR (500 MHz, CDCl₃): δ=p.p.m. 8.86 (s, 1H NH), 8.59 (d, J = 9.1 Hz, 1H naphthyridyl proton), 8.40 (d, J = 9.1 Hz, 1H naphthyridyl proton), 7.81 (s, 1H naphthyridyl proton), 6.77 (s, 1H CH), 2.79 (s, 3H), 2.32 (s, 3H).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg,1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with atom labels and 30% probability displacement ellipsoids, and the disorders of hydrogen atoms are shown.
	Fig. 2. A view of the crystal packing. Hydrogen bonds are shown as black dashed lines, while weak contacts as the blue ones.

N-(7-Dibromomethyl-5-methyl-1,8-naphthyridin-2-yl)acetamide– pyrrolidine-2,5-dione (1/1) top

Crystal data top

C₁₂H₁₁Br₂N₃O·C₄H₅NO₂	F(000) = 468
M_r = 472.15	D_x = 1.739 Mg m⁻³
Monoclinic, P2₁/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 25 reflections
a = 11.537 (2) Å	θ = 3.4–25.0°
b = 7.0093 (14) Å	µ = 4.52 mm⁻¹
c = 11.632 (2) Å	T = 293 K
β = 106.57 (3)°	Block, colourless
V = 901.6 (3) Å³	0.21 × 0.19 × 0.18 mm
Z = 2

Data collection top

Rigaku R-AXIS RAPID diffractometer	1723 independent reflections
Radiation source: fine-focus sealed tube	1220 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scan	θ_max = 25.0°, θ_min = 3.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→13
T_min = 0.450, T_max = 0.497	k = −8→7
7056 measured reflections	l = −13→13

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0757P)² + 1.6111P] where P = (F_o² + 2F_c²)/3
1723 reflections	(Δ/σ)_max < 0.001
148 parameters	Δρ_max = 0.72 e Å⁻³
0 restraints	Δρ_min = −0.92 e Å⁻³

Crystal data top

C₁₂H₁₁Br₂N₃O·C₄H₅NO₂	V = 901.6 (3) Å³
M_r = 472.15	Z = 2
Monoclinic, P2₁/m	Mo Kα radiation
a = 11.537 (2) Å	µ = 4.52 mm⁻¹
b = 7.0093 (14) Å	T = 293 K
c = 11.632 (2) Å	0.21 × 0.19 × 0.18 mm
β = 106.57 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	1723 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1220 reflections with I > 2σ(I)
T_min = 0.450, T_max = 0.497	R_int = 0.042
7056 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.164	H-atom parameters constrained
S = 1.12	Δρ_max = 0.72 e Å⁻³
1723 reflections	Δρ_min = −0.92 e Å⁻³
148 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	0.5310 (7)	0.2500	0.7838 (6)	0.0437 (17)
C2	0.4522 (7)	0.2500	0.8575 (7)	0.0486 (18)
H2A	0.3689	0.2500	0.8226	0.058*
C3	0.4977 (7)	0.2500	0.9803 (6)	0.0452 (17)
C4	0.6257 (7)	0.2500	1.0284 (6)	0.0405 (16)
C5	0.6882 (7)	0.2500	1.1520 (6)	0.0482 (18)
H5A	0.6446	0.2500	1.2080	0.058*
C6	0.8109 (7)	0.2500	1.1903 (7)	0.053 (2)
H6A	0.8518	0.2500	1.2717	0.063*
C7	0.8749 (6)	0.2500	1.1028 (6)	0.0456 (18)
C8	0.6974 (7)	0.2500	0.9487 (6)	0.0415 (16)
C9	0.4859 (8)	0.2500	0.6506 (7)	0.058 (2)
H9A	0.5554	0.2500	0.6180	0.069*
C10	0.4146 (7)	0.2500	1.0597 (7)	0.0491 (18)
H10A	0.3319	0.2500	1.0112	0.074*
H10B	0.4298	0.1382	1.1094	0.074*
C11	1.0841 (7)	0.2500	1.2427 (7)	0.055 (2)
C12	1.2128 (7)	0.2500	1.2408 (8)	0.067 (2)
H12A	1.2652	0.2500	1.3214	0.101*
H12B	1.2279	0.1382	1.1997	0.101*
C13	0.0377 (8)	0.2500	0.8080 (8)	0.057 (2)
C14	0.0885 (8)	0.2500	0.7021 (8)	0.069 (2)
H14A	0.1368	0.1384	0.7023	0.082*
C15	−0.0232 (9)	0.2500	0.5948 (8)	0.080 (3)
H15A	−0.0251	0.1387	0.5463	0.095*
C16	−0.1280 (8)	0.2500	0.6435 (8)	0.056 (2)
N1	0.6503 (6)	0.2500	0.8271 (5)	0.0477 (15)
N2	0.8206 (6)	0.2500	0.9860 (5)	0.0461 (15)
N3	1.0008 (6)	0.2500	1.1320 (5)	0.0524 (16)
H3A	1.0303	0.2500	1.0719	0.063*
N4	−0.0857 (6)	0.2500	0.7663 (5)	0.0502 (16)
H4A	−0.1322	0.2500	0.8124	0.060*
O1	1.0553 (6)	0.2500	1.3339 (5)	0.093 (3)
O2	0.0955 (5)	0.2500	0.9136 (5)	0.0759 (19)
O3	−0.2342 (6)	0.2500	0.5882 (6)	0.081 (2)
Br1	0.38805 (7)	0.02689 (12)	0.59139 (6)	0.0801 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.041 (4)	0.052 (4)	0.042 (4)	0.000	0.018 (3)	0.000
C2	0.043 (4)	0.060 (5)	0.045 (4)	0.000	0.018 (3)	0.000
C3	0.045 (4)	0.048 (4)	0.050 (4)	0.000	0.025 (4)	0.000
C4	0.044 (4)	0.044 (4)	0.039 (4)	0.000	0.020 (3)	0.000
C5	0.053 (5)	0.059 (5)	0.041 (4)	0.000	0.026 (3)	0.000
C6	0.046 (5)	0.079 (6)	0.036 (4)	0.000	0.016 (3)	0.000
C7	0.041 (4)	0.054 (4)	0.044 (4)	0.000	0.016 (3)	0.000
C8	0.046 (5)	0.046 (4)	0.035 (4)	0.000	0.018 (3)	0.000
C9	0.054 (5)	0.076 (6)	0.047 (4)	0.000	0.021 (4)	0.000
C10	0.041 (4)	0.062 (5)	0.051 (4)	0.000	0.024 (3)	0.000
C11	0.046 (5)	0.075 (6)	0.041 (4)	0.000	0.009 (4)	0.000
C12	0.042 (5)	0.102 (7)	0.057 (5)	0.000	0.012 (4)	0.000
C13	0.059 (6)	0.061 (5)	0.058 (5)	0.000	0.027 (4)	0.000
C14	0.059 (6)	0.083 (6)	0.074 (6)	0.000	0.034 (5)	0.000
C15	0.091 (8)	0.107 (8)	0.052 (5)	0.000	0.039 (5)	0.000
C16	0.054 (5)	0.061 (5)	0.054 (5)	0.000	0.017 (4)	0.000
N1	0.047 (4)	0.060 (4)	0.043 (3)	0.000	0.024 (3)	0.000
N2	0.042 (4)	0.062 (4)	0.039 (3)	0.000	0.020 (3)	0.000
N3	0.043 (4)	0.079 (5)	0.041 (3)	0.000	0.022 (3)	0.000
N4	0.042 (4)	0.070 (4)	0.042 (3)	0.000	0.017 (3)	0.000
O1	0.051 (4)	0.188 (8)	0.041 (3)	0.000	0.014 (3)	0.000
O2	0.054 (4)	0.114 (6)	0.057 (4)	0.000	0.012 (3)	0.000
O3	0.067 (5)	0.116 (6)	0.057 (4)	0.000	0.011 (3)	0.000
Br1	0.0936 (7)	0.0929 (6)	0.0563 (5)	−0.0237 (4)	0.0254 (4)	−0.0161 (3)

Geometric parameters (Å, º) top

C1—N1	1.324 (9)	C9—H9A	0.9800
C1—C2	1.417 (10)	C10—H10A	0.9600
C1—C9	1.487 (10)	C10—H10B	0.9600
C2—C3	1.373 (10)	C11—O1	1.199 (10)
C2—H2A	0.9300	C11—N3	1.370 (10)
C3—C4	1.422 (10)	C11—C12	1.490 (11)
C3—C10	1.509 (9)	C12—H12A	0.9600
C4—C8	1.407 (10)	C12—H12B	0.9601
C4—C5	1.413 (10)	C13—O2	1.220 (10)
C5—C6	1.357 (11)	C13—N4	1.367 (10)
C5—H5A	0.9300	C13—C14	1.508 (12)
C6—C7	1.418 (10)	C14—C15	1.517 (13)
C6—H6A	0.9300	C14—H14A	0.9600
C7—N2	1.324 (9)	C15—C16	1.474 (13)
C7—N3	1.394 (9)	C15—H15A	0.9600
C8—N1	1.363 (9)	C16—O3	1.210 (10)
C8—N2	1.363 (9)	C16—N4	1.372 (10)
C9—Br1	1.936 (5)	N3—H3A	0.8600
C9—Br1ⁱ	1.936 (5)	N4—H4A	0.8600

N1—C1—C2	123.1 (7)	C3—C10—H10A	109.8
N1—C1—C9	114.4 (6)	C3—C10—H10B	109.3
C2—C1—C9	122.4 (7)	H10A—C10—H10B	109.5
C3—C2—C1	120.5 (7)	O1—C11—N3	122.3 (8)
C3—C2—H2A	119.7	O1—C11—C12	122.8 (7)
C1—C2—H2A	119.7	N3—C11—C12	114.9 (7)
C2—C3—C4	117.1 (6)	C11—C12—H12A	109.8
C2—C3—C10	121.0 (7)	C11—C12—H12B	109.3
C4—C3—C10	121.9 (7)	H12A—C12—H12B	109.5
C8—C4—C5	116.5 (7)	O2—C13—N4	124.9 (8)
C8—C4—C3	118.7 (6)	O2—C13—C14	126.5 (8)
C5—C4—C3	124.9 (6)	N4—C13—C14	108.6 (8)
C6—C5—C4	121.0 (7)	C13—C14—C15	103.6 (7)
C6—C5—H5A	119.5	C13—C14—H14A	111.0
C4—C5—H5A	119.5	C15—C14—H14A	111.0
C5—C6—C7	118.2 (7)	C16—C15—C14	106.4 (7)
C5—C6—H6A	120.9	C16—C15—H15A	110.0
C7—C6—H6A	120.9	C14—C15—H15A	110.8
N2—C7—N3	113.9 (6)	O3—C16—N4	124.0 (8)
N2—C7—C6	123.1 (7)	O3—C16—C15	127.8 (8)
N3—C7—C6	123.1 (7)	N4—C16—C15	108.2 (8)
N1—C8—N2	113.6 (6)	C1—N1—C8	117.3 (6)
N1—C8—C4	123.3 (7)	C7—N2—C8	118.1 (6)
N2—C8—C4	123.1 (6)	C11—N3—C7	129.2 (7)
C1—C9—Br1	111.5 (3)	C11—N3—H3A	115.4
C1—C9—Br1ⁱ	111.5 (3)	C7—N3—H3A	115.4
Br1—C9—Br1ⁱ	107.7 (4)	C16—N4—C13	113.2 (7)
C1—C9—H9A	108.7	C16—N4—H4A	123.4
Br1—C9—H9A	108.7	C13—N4—H4A	123.4
Br1ⁱ—C9—H9A	108.7

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O1	0.93	2.25	2.838 (10)	121
C9—H9A···O3ⁱⁱ	0.98	2.55	3.507 (11)	166
N4—H4A···N1ⁱⁱⁱ	0.86	2.56	3.317 (9)	147
N4—H4A···N2ⁱⁱⁱ	0.86	2.24	3.045 (8)	157
N3—H3A···O2ⁱⁱ	0.86	2.18	3.038 (9)	177

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₁Br₂N₃O·C₄H₅NO₂
M_r	472.15
Crystal system, space group	Monoclinic, P2₁/m
Temperature (K)	293
a, b, c (Å)	11.537 (2), 7.0093 (14), 11.632 (2)
β (°)	106.57 (3)
V (Å³)	901.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.52
Crystal size (mm)	0.21 × 0.19 × 0.18

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.450, 0.497
No. of measured, independent and observed [I > 2σ(I)] reflections	7056, 1723, 1220
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.164, 1.12
No. of reflections	1723
No. of parameters	148
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.92

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg,1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O1	0.93	2.25	2.838 (10)	121
C9—H9A···O3ⁱ	0.98	2.55	3.507 (11)	166
N4—H4A···N1ⁱⁱ	0.86	2.56	3.317 (9)	147
N4—H4A···N2ⁱⁱ	0.86	2.24	3.045 (8)	157
N3—H3A···O2ⁱ	0.86	2.18	3.038 (9)	177

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

Acknowledgements

Support is acknowledged from the `Spring Sunshine' Plan of the Ministry of Education of China (grant No. Z2011125) and the National Natural Science Foundation of China (grant No. 21262049)

References

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Pages o153-o154

doi:10.1107/S1600536812051112

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

N-(7-Di­bromo­methyl-5-methyl-1,8-naphthyridin-2-yl)acetamide–pyrrolidine-2,5-dione (1/1)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-(7-Dibromomethyl-5-methyl-1,8-naphthyridin-2-yl)acetamide–pyrrolidine-2,5-dione (1/1)