N,N′-Bis(4-methyl­phen­yl)naphthalene-1,4-dicarboxamide N,N-dimethyl­acetamide disolvate

Jing, L.-H.

doi:10.1107/S1600536808037422

organic compounds

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Volume 64| Part 12| December 2008| Page o2379

doi:10.1107/S1600536808037422

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N,N′-Bis(4-methylphenyl)naphthalene-1,4-dicarboxamide N,N-dimethylacetamide disolvate

Lin-Hai Jing ^a ^*

^aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: jlhjhr@yahoo.com.cn

(Received 27 October 2008; accepted 11 November 2008; online 20 November 2008)

The title compound, C₂₆H₂₂N₂O₂·2C₄H₉NO, crystallizes in an anti C=O orientation. The two amide groups are approximately perpendicular to the naphthalene ring system [dihedral angles = 88.89 (1) and 89.08 (1)°]. Each of the dimethylacetamide solvent molecules are disordered over two positions, with occupancies of 0.655 (12):0.345 (12) and 0.531 (13):0.469 (13). The crystal packing is stabilized by N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For general background to the application of 1,4-naphthalenedicarboxylic acid derivatives as monomers in the preparation of polymers, see: Fukuzumi et al. (1994 ); Tsukada et al. (1994 ). For related structures, see: Jing et al. (2006a ,b ).

Experimental

Crystal data

C₂₆H₂₂N₂O₂·2C₄H₉NO
M_r = 568.70
Monoclinic, P 2₁ /c
a = 13.270 (3) Å
b = 20.285 (4) Å
c = 12.125 (3) Å
β = 101.021 (4)°
V = 3203.7 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 294 (2) K
0.24 × 0.22 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.982, T_max = 0.988
16193 measured reflections
5652 independent reflections
2347 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.186
S = 1.00
5652 reflections
491 parameters
166 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4	0.86	2.02	2.880 (15)	175
N2—H2N⋯O3ⁱ	0.86	1.99	2.821 (13)	162
C24—H24⋯O1ⁱⁱ	0.93	2.57	3.466 (5)	163
C17—H17⋯O1	0.93	2.33	2.911 (4)	120
C25—H25⋯O2	0.93	2.33	2.907 (4)	120
Symmetry codes: (i) x, y-1, z; (ii) x-1, y, z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037422/ci2697sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808037422/ci2697Isup2.hkl

checkCIF report

Comment top

1,4-Naphthalenedicarboxylic acid derivatives are a class of intermediates important for applications as monomers in the preparation of polymers (Fukuzumi et al., 1994; Tsukada et al., 1994). Previously, we have reported the crystal structures of N,N'-bis(4-nitrophenyl)naphthalene-1,4-dicarboxamide dimethylsulfoxide disolvate (Jing et al., 2006a) and N,N'-bis(2-methoxyphenyl)naphthalene-1,4-dicarboxamide (Jing et al., 2006b). We now report the crystal structure of the title compound.

Bond lengths and angles in the title compound are normal. The naphthalene ring system is planar, with a maximum deviation of 0.025 (1) Å for atom C3. The two C?O gruops exhibit anti orientations. As a result of steric effects, the substituent groups at atoms C1 and C4 are twisted away from the plane of the naphthalene ring system (Fig. 1). The O1/N1/C1/C11 and O2/N2/C4/C19 planes form dihedral angles of 88.89 (1) and 89.08 (1)°, respectively, with the C1—C4/C9/C10 plane. The O1/N1/C1/C11 and C12—C17 planes are inclined at an angle of 7.48 (2)° while the O2/N2/C4/C19 and C20—C25 planes make a dihedral angle of 11.10 (2)°. The crystal packing is stabilized by N—H···O and C—H···O hydrogen bonds (Table 1).

Related literature top

For general background to the application of 1,4-naphthalenedicarboxylic acid derivatives as monomers in the preparation of polymers, see: Fukuzumi et al. (1994); Tsukada et al. (1994). For related structures, see: Jing et al. (2006a,b).

Experimental top

Naphthalene-1,4-dicarboxylic acid (2 mmol) and an excess of thionyl chloride (6 mmol) in dioxane (20 ml) were boiled under reflux for 6 h. The solution was distilled under reduced pressure and a yellow solid was obtained. P-toluidine (4 mmol) in tetrahydrofuran (20 ml) was added to the yellow solid and boiled under reflux for 1 d. The solution was then cooled to ambient temperature and filtered to remove the tetrahydrofuran. The precipitate was dissolved in dimethylacetamide and allowed to stand for one month at ambient temperature, after which time colourless single crystals of the title compound suitable for X-ray diffraction were obtained.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level. All disordered components are shown. H atoms have been omitted for clarity.

N,N'-Bis(4-methylphenyl)naphthalene-1,4-dicarboxamide N,N-dimethylacetamide disolvate top

Crystal data top

C₂₆H₂₂N₂O₂·2C₄H₉NO	F(000) = 1216
M_r = 568.70	D_x = 1.179 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2185 reflections
a = 13.270 (3) Å	θ = 2.3–20.1°
b = 20.285 (4) Å	µ = 0.08 mm⁻¹
c = 12.125 (3) Å	T = 294 K
β = 101.021 (4)°	Block, colourless
V = 3203.7 (12) Å³	0.24 × 0.22 × 0.16 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	5652 independent reflections
Radiation source: fine-focus sealed tube	2347 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→13
T_min = 0.982, T_max = 0.988	k = −22→24
16193 measured reflections	l = −14→14

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.186	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0808P)² + 0.1377P] where P = (F_o² + 2F_c²)/3
5652 reflections	(Δ/σ)_max = 0.001
491 parameters	Δρ_max = 0.20 e Å⁻³
166 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₆H₂₂N₂O₂·2C₄H₉NO	V = 3203.7 (12) Å³
M_r = 568.70	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.270 (3) Å	µ = 0.08 mm⁻¹
b = 20.285 (4) Å	T = 294 K
c = 12.125 (3) Å	0.24 × 0.22 × 0.16 mm
β = 101.021 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5652 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2347 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.988	R_int = 0.057
16193 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	166 restraints
wR(F²) = 0.186	H-atom parameters constrained
S = 1.00	Δρ_max = 0.20 e Å⁻³
5652 reflections	Δρ_min = −0.18 e Å⁻³
491 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	Occ. (<1)
O1	0.4931 (2)	0.09472 (15)	0.2665 (3)	0.1430 (14)
O2	−0.05256 (19)	0.11822 (14)	0.3003 (3)	0.1171 (11)
N1	0.46882 (18)	0.18251 (13)	0.3719 (2)	0.0666 (8)
H1N	0.4215	0.2032	0.3973	0.080*
N2	−0.03759 (18)	0.02910 (13)	0.1927 (2)	0.0664 (8)
H2N	0.0069	0.0073	0.1643	0.080*
C1	0.3245 (2)	0.11496 (15)	0.2971 (3)	0.0594 (9)
C2	0.2572 (3)	0.14196 (16)	0.2104 (3)	0.0777 (11)
H2	0.2814	0.1693	0.1596	0.093*
C3	0.1517 (3)	0.12923 (17)	0.1964 (3)	0.0765 (10)
H3	0.1072	0.1479	0.1360	0.092*
C4	0.1134 (2)	0.09031 (15)	0.2692 (3)	0.0591 (9)
C5	0.1465 (3)	0.01648 (19)	0.4362 (3)	0.0829 (11)
H5	0.0766	0.0080	0.4282	0.100*
C6	0.2130 (4)	−0.0127 (2)	0.5205 (4)	0.1090 (15)
H6	0.1886	−0.0409	0.5699	0.131*
C7	0.3182 (3)	−0.0005 (2)	0.5337 (4)	0.1084 (14)
H7	0.3633	−0.0207	0.5920	0.130*
C8	0.3555 (3)	0.0403 (2)	0.4629 (3)	0.0825 (11)
H8	0.4258	0.0476	0.4731	0.099*
C9	0.2886 (2)	0.07204 (16)	0.3732 (3)	0.0592 (9)
C10	0.1816 (2)	0.05967 (16)	0.3599 (3)	0.0593 (8)
C11	0.4374 (3)	0.12956 (19)	0.3096 (3)	0.0738 (10)
C12	0.5683 (2)	0.20955 (16)	0.4022 (3)	0.0609 (9)
C13	0.5808 (3)	0.26050 (16)	0.4800 (3)	0.0708 (10)
H13	0.5248	0.2755	0.5087	0.085*
C14	0.6758 (3)	0.28904 (17)	0.5148 (3)	0.0814 (11)
H14	0.6825	0.3231	0.5671	0.098*
C15	0.7607 (3)	0.26879 (19)	0.4749 (3)	0.0771 (10)
C16	0.7470 (3)	0.2176 (2)	0.3972 (4)	0.0871 (12)
H16	0.8033	0.2023	0.3693	0.104*
C17	0.6523 (3)	0.18870 (17)	0.3603 (3)	0.0778 (10)
H17	0.6453	0.1551	0.3071	0.093*
C18	0.8651 (3)	0.2990 (2)	0.5168 (4)	0.1091 (14)
H18A	0.8603	0.3461	0.5098	0.164*
H18B	0.9128	0.2827	0.4729	0.164*
H18C	0.8884	0.2874	0.5942	0.164*
C19	−0.0006 (2)	0.08077 (18)	0.2561 (3)	0.0666 (9)
C20	−0.1393 (2)	0.00511 (16)	0.1657 (3)	0.0575 (8)
C21	−0.1533 (3)	−0.05613 (17)	0.1166 (3)	0.0768 (10)
H21	−0.0971	−0.0799	0.1029	0.092*
C22	−0.2507 (3)	−0.08224 (18)	0.0876 (3)	0.0858 (11)
H22	−0.2588	−0.1237	0.0545	0.103*
C23	−0.3361 (3)	−0.0490 (2)	0.1061 (3)	0.0756 (10)
C24	−0.3205 (2)	0.0123 (2)	0.1551 (3)	0.0714 (10)
H24	−0.3769	0.0360	0.1688	0.086*
C25	−0.2237 (2)	0.03961 (16)	0.1848 (3)	0.0639 (9)
H25	−0.2156	0.0812	0.2175	0.077*
C26	−0.4417 (3)	−0.0792 (2)	0.0734 (4)	0.1198 (16)
H26A	−0.4894	−0.0549	0.1080	0.180*
H26B	−0.4396	−0.1242	0.0982	0.180*
H26C	−0.4632	−0.0776	−0.0068	0.180*
O3	0.1070 (8)	0.9382 (7)	0.1400 (9)	0.095 (3)	0.655 (12)
N3	0.2684 (5)	0.9101 (3)	0.2237 (5)	0.081 (2)	0.655 (12)
C27	0.1348 (13)	0.8495 (10)	0.2960 (17)	0.137 (6)	0.655 (12)
H27A	0.1942	0.8346	0.3480	0.206*	0.655 (12)
H27B	0.1039	0.8130	0.2516	0.206*	0.655 (12)
H27C	0.0862	0.8680	0.3368	0.206*	0.655 (12)
C28	0.1664 (6)	0.9019 (4)	0.2194 (7)	0.083 (3)	0.655 (12)
C29	0.2879 (11)	0.9599 (10)	0.1401 (15)	0.088 (5)	0.655 (12)
H29A	0.2241	0.9793	0.1041	0.131*	0.655 (12)
H29B	0.3199	0.9390	0.0847	0.131*	0.655 (12)
H29C	0.3324	0.9937	0.1776	0.131*	0.655 (12)
C30	0.3530 (10)	0.8759 (9)	0.2965 (15)	0.126 (5)	0.655 (12)
H30A	0.3258	0.8429	0.3395	0.190*	0.655 (12)
H30B	0.3927	0.9070	0.3465	0.190*	0.655 (12)
H30C	0.3961	0.8552	0.2513	0.190*	0.655 (12)
O3'	0.0993 (13)	0.9258 (12)	0.1737 (17)	0.080 (5)	0.345 (12)
N3'	0.2233 (13)	0.8814 (6)	0.2616 (10)	0.090 (5)	0.345 (12)
C27'	0.301 (2)	0.953 (2)	0.143 (4)	0.130 (17)	0.345 (12)
H27D	0.2850	0.9856	0.0839	0.194*	0.345 (12)
H27E	0.3365	0.9170	0.1168	0.194*	0.345 (12)
H27F	0.3434	0.9730	0.2071	0.194*	0.345 (12)
C28'	0.2000 (11)	0.9283 (6)	0.1748 (10)	0.071 (5)	0.345 (12)
C29'	0.3298 (15)	0.8591 (17)	0.298 (3)	0.124 (10)	0.345 (12)
H29D	0.3735	0.8830	0.2571	0.187*	0.345 (12)
H29E	0.3342	0.8128	0.2829	0.187*	0.345 (12)
H29F	0.3515	0.8670	0.3768	0.187*	0.345 (12)
C30'	0.151 (3)	0.844 (3)	0.315 (4)	0.190 (19)	0.345 (12)
H30D	0.0819	0.8562	0.2829	0.286*	0.345 (12)
H30E	0.1641	0.8526	0.3944	0.286*	0.345 (12)
H30F	0.1598	0.7973	0.3033	0.286*	0.345 (12)
O4	0.3102 (10)	0.2454 (9)	0.4665 (12)	0.084 (3)	0.531 (13)
N4	0.1781 (6)	0.2063 (5)	0.5319 (8)	0.096 (4)	0.531 (13)
C31	0.3555 (14)	0.1799 (13)	0.6528 (16)	0.151 (7)	0.531 (13)
H31A	0.3158	0.1577	0.7001	0.227*	0.531 (13)
H31B	0.3969	0.2133	0.6954	0.227*	0.531 (13)
H31C	0.3990	0.1486	0.6253	0.227*	0.531 (13)
C32	0.2843 (6)	0.2111 (5)	0.5553 (10)	0.085 (4)	0.531 (13)
C33	0.1296 (13)	0.2400 (13)	0.4258 (17)	0.098 (8)	0.531 (13)
H33A	0.1820	0.2583	0.3904	0.147*	0.531 (13)
H33B	0.0855	0.2746	0.4426	0.147*	0.531 (13)
H33C	0.0898	0.2087	0.3761	0.147*	0.531 (13)
C34	0.1140 (10)	0.1725 (7)	0.5989 (12)	0.108 (4)	0.531 (13)
H34A	0.1568	0.1486	0.6584	0.162*	0.531 (13)
H34B	0.0690	0.1424	0.5522	0.162*	0.531 (13)
H34C	0.0740	0.2043	0.6305	0.162*	0.531 (13)
O4'	0.3332 (11)	0.2433 (12)	0.5008 (14)	0.096 (5)	0.469 (13)
N4'	0.2303 (10)	0.1904 (5)	0.5850 (9)	0.100 (4)	0.469 (13)
C31'	0.1215 (14)	0.241 (2)	0.436 (2)	0.134 (14)	0.469 (13)
H31D	0.1186	0.2660	0.3683	0.201*	0.469 (13)
H31E	0.0891	0.2653	0.4875	0.201*	0.469 (13)
H31F	0.0863	0.1998	0.4185	0.201*	0.469 (13)
C32'	0.2346 (10)	0.2275 (5)	0.4902 (9)	0.083 (4)	0.469 (13)
C33'	0.1508 (14)	0.1589 (12)	0.6330 (19)	0.181 (10)	0.469 (13)
H33D	0.0851	0.1670	0.5860	0.271*	0.469 (13)
H33E	0.1513	0.1764	0.7066	0.271*	0.469 (13)
H33F	0.1631	0.1122	0.6382	0.271*	0.469 (13)
C34'	0.3217 (13)	0.1756 (14)	0.6665 (19)	0.129 (6)	0.469 (13)
H34D	0.3804	0.1939	0.6419	0.193*	0.469 (13)
H34E	0.3295	0.1287	0.6741	0.193*	0.469 (13)
H34F	0.3161	0.1945	0.7377	0.193*	0.469 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0691 (18)	0.147 (3)	0.216 (4)	−0.0110 (18)	0.037 (2)	−0.109 (3)
O2	0.0686 (17)	0.127 (2)	0.155 (3)	−0.0018 (16)	0.0209 (17)	−0.079 (2)
N1	0.0541 (17)	0.0594 (18)	0.087 (2)	−0.0032 (14)	0.0153 (14)	−0.0136 (16)
N2	0.0448 (16)	0.0693 (19)	0.083 (2)	0.0012 (14)	0.0061 (13)	−0.0180 (16)
C1	0.054 (2)	0.054 (2)	0.067 (2)	0.0004 (16)	0.0042 (17)	−0.0066 (18)
C2	0.069 (3)	0.070 (2)	0.091 (3)	−0.006 (2)	0.008 (2)	0.019 (2)
C3	0.061 (2)	0.079 (3)	0.081 (3)	−0.0011 (19)	−0.0060 (19)	0.020 (2)
C4	0.055 (2)	0.057 (2)	0.062 (2)	−0.0039 (16)	0.0025 (17)	−0.0029 (18)
C5	0.076 (2)	0.099 (3)	0.076 (3)	−0.003 (2)	0.020 (2)	0.011 (2)
C6	0.106 (4)	0.141 (4)	0.081 (3)	0.014 (3)	0.021 (3)	0.045 (3)
C7	0.097 (4)	0.147 (4)	0.076 (3)	0.023 (3)	0.004 (3)	0.032 (3)
C8	0.067 (2)	0.110 (3)	0.065 (3)	0.015 (2)	0.001 (2)	0.002 (2)
C9	0.059 (2)	0.065 (2)	0.050 (2)	0.0054 (17)	0.0028 (16)	−0.0054 (17)
C10	0.057 (2)	0.064 (2)	0.056 (2)	0.0008 (17)	0.0071 (16)	−0.0060 (18)
C11	0.058 (2)	0.073 (3)	0.090 (3)	0.002 (2)	0.0111 (19)	−0.019 (2)
C12	0.052 (2)	0.053 (2)	0.078 (2)	−0.0033 (17)	0.0124 (17)	0.0028 (18)
C13	0.061 (2)	0.058 (2)	0.093 (3)	0.0001 (18)	0.0137 (19)	−0.006 (2)
C14	0.071 (3)	0.064 (2)	0.104 (3)	−0.010 (2)	0.004 (2)	−0.005 (2)
C15	0.059 (2)	0.070 (3)	0.098 (3)	−0.010 (2)	0.004 (2)	0.011 (2)
C16	0.060 (2)	0.088 (3)	0.118 (3)	−0.005 (2)	0.029 (2)	0.006 (3)
C17	0.065 (2)	0.074 (2)	0.098 (3)	−0.011 (2)	0.027 (2)	−0.016 (2)
C18	0.065 (3)	0.108 (3)	0.146 (4)	−0.022 (2)	0.001 (2)	0.018 (3)
C19	0.056 (2)	0.070 (2)	0.069 (2)	0.001 (2)	−0.0005 (18)	−0.007 (2)
C20	0.050 (2)	0.060 (2)	0.061 (2)	0.0030 (17)	0.0064 (15)	−0.0033 (17)
C21	0.061 (2)	0.064 (2)	0.102 (3)	0.0051 (19)	0.0074 (19)	−0.013 (2)
C22	0.071 (3)	0.066 (2)	0.115 (3)	−0.009 (2)	0.004 (2)	−0.008 (2)
C23	0.057 (2)	0.077 (3)	0.089 (3)	−0.010 (2)	0.0021 (19)	0.012 (2)
C24	0.051 (2)	0.094 (3)	0.068 (2)	0.006 (2)	0.0067 (17)	0.006 (2)
C25	0.057 (2)	0.071 (2)	0.060 (2)	0.0074 (19)	0.0031 (16)	−0.0025 (17)
C26	0.070 (3)	0.117 (3)	0.163 (4)	−0.027 (2)	−0.003 (3)	0.019 (3)
O3	0.081 (5)	0.094 (6)	0.111 (7)	0.022 (3)	0.026 (4)	0.003 (5)
N3	0.079 (4)	0.080 (4)	0.085 (4)	0.016 (3)	0.017 (3)	0.008 (3)
C27	0.157 (9)	0.145 (9)	0.126 (8)	−0.038 (6)	0.070 (6)	0.034 (6)
C28	0.086 (6)	0.081 (6)	0.085 (6)	0.013 (5)	0.024 (5)	−0.012 (4)
C29	0.105 (7)	0.084 (7)	0.086 (7)	−0.017 (5)	0.048 (5)	0.005 (4)
C30	0.120 (7)	0.116 (8)	0.127 (7)	0.042 (7)	−0.018 (6)	0.013 (6)
O3'	0.069 (7)	0.084 (8)	0.084 (9)	0.030 (6)	0.004 (6)	0.014 (6)
N3'	0.095 (9)	0.087 (8)	0.091 (8)	−0.003 (7)	0.024 (6)	0.009 (6)
C27'	0.143 (19)	0.120 (19)	0.133 (19)	−0.002 (9)	0.045 (10)	0.008 (10)
C28'	0.065 (9)	0.073 (8)	0.081 (8)	0.000 (7)	0.024 (7)	−0.006 (6)
C29'	0.119 (13)	0.113 (13)	0.127 (12)	0.005 (9)	−0.013 (8)	0.027 (9)
C30'	0.19 (2)	0.19 (2)	0.19 (2)	−0.004 (10)	0.056 (11)	0.021 (10)
O4	0.049 (5)	0.081 (5)	0.124 (8)	−0.005 (4)	0.025 (5)	−0.023 (6)
N4	0.107 (6)	0.089 (6)	0.100 (7)	−0.006 (5)	0.041 (5)	−0.014 (5)
C31	0.169 (11)	0.133 (9)	0.147 (10)	0.028 (9)	0.018 (8)	0.001 (7)
C32	0.081 (6)	0.083 (7)	0.097 (8)	−0.002 (6)	0.031 (6)	−0.029 (5)
C33	0.078 (9)	0.103 (10)	0.110 (10)	−0.010 (6)	0.010 (6)	−0.035 (7)
C34	0.117 (7)	0.109 (7)	0.115 (7)	−0.019 (6)	0.065 (6)	0.013 (6)
O4'	0.083 (8)	0.098 (7)	0.108 (8)	−0.017 (6)	0.025 (6)	−0.025 (6)
N4'	0.127 (9)	0.084 (6)	0.094 (7)	0.001 (6)	0.032 (6)	−0.014 (5)
C31'	0.126 (16)	0.145 (16)	0.136 (16)	−0.001 (9)	0.034 (9)	−0.024 (9)
C32'	0.085 (8)	0.068 (6)	0.093 (7)	0.008 (6)	0.011 (7)	−0.026 (5)
C33'	0.196 (13)	0.186 (13)	0.172 (12)	−0.016 (9)	0.063 (9)	0.015 (9)
C34'	0.121 (9)	0.127 (9)	0.139 (10)	0.017 (8)	0.025 (8)	0.014 (7)

Geometric parameters (Å, º) top

O1—C11	1.211 (4)	N3—C28	1.356 (7)
O2—C19	1.216 (4)	N3—C29	1.488 (10)
N1—C11	1.333 (4)	N3—C30	1.464 (8)
N1—C12	1.411 (4)	C27—C28	1.522 (9)
N1—H1N	0.86	C27—H27A	0.96
N2—C19	1.337 (4)	C27—H27B	0.96
N2—C20	1.413 (4)	C27—H27C	0.96
N2—H2N	0.86	C29—H29A	0.96
C1—C2	1.358 (4)	C29—H29B	0.96
C1—C9	1.416 (4)	C29—H29C	0.96
C1—C11	1.506 (4)	C30—H30A	0.96
C2—C3	1.401 (4)	C30—H30B	0.96
C2—H2	0.93	C30—H30C	0.96
C3—C4	1.353 (4)	O3'—C28'	1.336 (15)
C3—H3	0.93	N3'—C28'	1.409 (10)
C4—C10	1.426 (4)	N3'—C30'	1.473 (11)
C4—C19	1.504 (4)	N3'—C29'	1.469 (10)
C5—C6	1.352 (5)	C27'—C28'	1.549 (11)
C5—C10	1.416 (4)	C27'—H27D	0.96
C5—H5	0.93	C27'—H27E	0.96
C6—C7	1.397 (5)	C27'—H27F	0.96
C6—H6	0.93	C29'—H29D	0.96
C7—C8	1.351 (5)	C29'—H29E	0.96
C7—H7	0.93	C29'—H29F	0.96
C8—C9	1.421 (4)	C30'—H30D	0.96
C8—H8	0.93	C30'—H30E	0.96
C9—C10	1.420 (4)	C30'—H30F	0.96
C12—C17	1.378 (4)	O4—C32	1.379 (13)
C12—C13	1.387 (4)	N4—C32	1.388 (9)
C13—C14	1.378 (4)	N4—C34	1.454 (8)
C13—H13	0.93	N4—C33	1.490 (10)
C14—C15	1.372 (5)	C31—C32	1.505 (10)
C14—H14	0.93	C31—H31A	0.96
C15—C16	1.391 (5)	C31—H31B	0.96
C15—C18	1.511 (4)	C31—H31C	0.96
C16—C17	1.381 (4)	C33—H33A	0.96
C16—H16	0.93	C33—H33B	0.96
C17—H17	0.93	C33—H33C	0.96
C18—H18A	0.96	C34—H34A	0.96
C18—H18B	0.96	C34—H34B	0.96
C18—H18C	0.96	C34—H34C	0.96
C20—C21	1.375 (4)	O4'—C32'	1.329 (14)
C20—C25	1.378 (4)	N4'—C32'	1.384 (9)
C21—C22	1.379 (4)	N4'—C34'	1.442 (10)
C21—H21	0.93	N4'—C33'	1.447 (10)
C22—C23	1.374 (5)	C31'—C32'	1.544 (11)
C22—H22	0.93	C31'—H31D	0.96
C23—C24	1.376 (5)	C31'—H31E	0.96
C23—C26	1.511 (5)	C31'—H31F	0.96
C24—C25	1.382 (4)	C33'—H33D	0.96
C24—H24	0.93	C33'—H33E	0.96
C25—H25	0.93	C33'—H33F	0.96
C26—H26A	0.96	C34'—H34D	0.96
C26—H26B	0.96	C34'—H34E	0.96
C26—H26C	0.96	C34'—H34F	0.96
O3—C28	1.342 (11)

C11—N1—C12	129.5 (3)	C28—C27—H27A	109.5
C11—N1—H1N	115.2	C28—C27—H27B	109.4
C12—N1—H1N	115.2	H27A—C27—H27B	109.5
C19—N2—C20	129.2 (3)	C28—C27—H27C	109.5
C19—N2—H2N	115.4	H27A—C27—H27C	109.5
C20—N2—H2N	115.4	H27B—C27—H27C	109.5
C2—C1—C9	119.9 (3)	O3—C28—N3	113.9 (10)
C2—C1—C11	119.5 (3)	O3—C28—C27	128.9 (11)
C9—C1—C11	120.5 (3)	N3—C28—C27	116.9 (10)
C1—C2—C3	120.9 (3)	N3—C29—H29A	109.5
C1—C2—H2	119.6	N3—C29—H29B	109.5
C3—C2—H2	119.6	H29A—C29—H29B	109.5
C4—C3—C2	121.3 (3)	N3—C29—H29C	109.4
C4—C3—H3	119.3	H29A—C29—H29C	109.5
C2—C3—H3	119.3	H29B—C29—H29C	109.5
C3—C4—C10	119.7 (3)	N3—C30—H30A	109.5
C3—C4—C19	120.1 (3)	N3—C30—H30B	109.4
C10—C4—C19	120.2 (3)	H30A—C30—H30B	109.5
C6—C5—C10	121.1 (4)	N3—C30—H30C	109.5
C6—C5—H5	119.4	H30A—C30—H30C	109.5
C10—C5—H5	119.4	H30B—C30—H30C	109.5
C5—C6—C7	120.2 (4)	C28'—N3'—C30'	128 (3)
C5—C6—H6	119.9	C28'—N3'—C29'	119.4 (19)
C7—C6—H6	119.9	C30'—N3'—C29'	112 (3)
C8—C7—C6	121.0 (4)	C28'—C27'—H27D	109.4
C8—C7—H7	119.5	C28'—C27'—H27E	109.5
C6—C7—H7	119.5	H27D—C27'—H27E	109.5
C7—C8—C9	120.9 (4)	C28'—C27'—H27F	109.6
C7—C8—H8	119.6	H27D—C27'—H27F	109.5
C9—C8—H8	119.6	H27E—C27'—H27F	109.5
C1—C9—C10	119.2 (3)	O3'—C28'—N3'	93.4 (16)
C1—C9—C8	122.6 (3)	O3'—C28'—C27'	157 (2)
C10—C9—C8	118.1 (3)	N3'—C28'—C27'	109 (2)
C5—C10—C9	118.8 (3)	N3'—C29'—H29D	109.4
C5—C10—C4	122.3 (3)	N3'—C29'—H29E	109.4
C9—C10—C4	118.9 (3)	H29D—C29'—H29E	109.5
O1—C11—N1	124.3 (3)	N3'—C29'—H29F	109.6
O1—C11—C1	121.3 (3)	H29D—C29'—H29F	109.5
N1—C11—C1	114.4 (3)	H29E—C29'—H29F	109.5
C17—C12—C13	118.6 (3)	N3'—C30'—H30D	109.5
C17—C12—N1	124.6 (3)	N3'—C30'—H30E	109.4
C13—C12—N1	116.8 (3)	H30D—C30'—H30E	109.5
C14—C13—C12	120.4 (3)	N3'—C30'—H30F	109.6
C14—C13—H13	119.8	H30D—C30'—H30F	109.5
C12—C13—H13	119.8	H30E—C30'—H30F	109.5
C15—C14—C13	122.0 (4)	C32—N4—C34	126.8 (12)
C15—C14—H14	119.0	C32—N4—C33	113.5 (12)
C13—C14—H14	119.0	C34—N4—C33	119.8 (11)
C14—C15—C16	117.0 (3)	C32—C31—H31A	109.4
C14—C15—C18	121.5 (4)	C32—C31—H31B	109.5
C16—C15—C18	121.5 (4)	H31A—C31—H31B	109.5
C17—C16—C15	121.9 (3)	C32—C31—H31C	109.5
C17—C16—H16	119.0	H31A—C31—H31C	109.5
C15—C16—H16	119.0	H31B—C31—H31C	109.5
C12—C17—C16	120.1 (3)	O4—C32—N4	105.8 (12)
C12—C17—H17	120.0	O4—C32—C31	127.8 (12)
C16—C17—H17	120.0	N4—C32—C31	126.2 (13)
C15—C18—H18A	109.5	N4—C33—H33A	109.5
C15—C18—H18B	109.5	N4—C33—H33B	109.5
H18A—C18—H18B	109.5	H33A—C33—H33B	109.5
C15—C18—H18C	109.5	N4—C33—H33C	109.5
H18A—C18—H18C	109.5	H33A—C33—H33C	109.5
H18B—C18—H18C	109.5	H33B—C33—H33C	109.5
O2—C19—N2	124.5 (3)	N4—C34—H34A	109.5
O2—C19—C4	121.1 (3)	N4—C34—H34B	109.5
N2—C19—C4	114.4 (3)	H34A—C34—H34B	109.5
C21—C20—C25	119.0 (3)	N4—C34—H34C	109.5
C21—C20—N2	117.1 (3)	H34A—C34—H34C	109.5
C25—C20—N2	123.9 (3)	H34B—C34—H34C	109.5
C20—C21—C22	120.0 (3)	C32'—N4'—C34'	121.2 (16)
C20—C21—H21	120.0	C32'—N4'—C33'	136.3 (16)
C22—C21—H21	120.0	C34'—N4'—C33'	102.4 (15)
C23—C22—C21	122.2 (4)	C32'—C31'—H31D	109.4
C23—C22—H22	118.9	C32'—C31'—H31E	109.5
C21—C22—H22	118.9	H31D—C31'—H31E	109.5
C22—C23—C24	117.0 (3)	C32'—C31'—H31F	109.5
C22—C23—C26	120.7 (4)	H31D—C31'—H31F	109.5
C24—C23—C26	122.3 (4)	H31E—C31'—H31F	109.5
C23—C24—C25	122.0 (3)	O4'—C32'—N4'	104.4 (15)
C23—C24—H24	119.0	O4'—C32'—C31'	149.1 (17)
C25—C24—H24	119.0	N4'—C32'—C31'	104.9 (16)
C20—C25—C24	119.9 (3)	N4'—C33'—H33D	109.5
C20—C25—H25	120.1	N4'—C33'—H33E	109.5
C24—C25—H25	120.1	H33D—C33'—H33E	109.5
C23—C26—H26A	109.5	N4'—C33'—H33F	109.5
C23—C26—H26B	109.5	H33D—C33'—H33F	109.5
H26A—C26—H26B	109.5	H33E—C33'—H33F	109.5
C23—C26—H26C	109.5	N4'—C34'—H34D	109.5
H26A—C26—H26C	109.5	N4'—C34'—H34E	109.5
H26B—C26—H26C	109.5	H34D—C34'—H34E	109.5
C28—N3—C29	111.1 (9)	N4'—C34'—H34F	109.5
C28—N3—C30	127.6 (10)	H34D—C34'—H34F	109.5
C29—N3—C30	121.3 (10)	H34E—C34'—H34F	109.5

C9—C1—C2—C3	1.6 (5)	C18—C15—C16—C17	178.5 (3)
C11—C1—C2—C3	179.9 (3)	C13—C12—C17—C16	1.2 (5)
C1—C2—C3—C4	0.7 (5)	N1—C12—C17—C16	−178.7 (3)
C2—C3—C4—C10	−2.2 (5)	C15—C16—C17—C12	−1.4 (6)
C2—C3—C4—C19	176.3 (3)	C20—N2—C19—O2	−2.2 (6)
C10—C5—C6—C7	0.0 (6)	C20—N2—C19—C4	178.2 (3)
C5—C6—C7—C8	−0.1 (7)	C3—C4—C19—O2	−88.3 (4)
C6—C7—C8—C9	0.2 (7)	C10—C4—C19—O2	90.2 (4)
C2—C1—C9—C10	−2.2 (5)	C3—C4—C19—N2	91.3 (4)
C11—C1—C9—C10	179.4 (3)	C10—C4—C19—N2	−90.2 (4)
C2—C1—C9—C8	177.5 (3)	C19—N2—C20—C21	−167.9 (3)
C11—C1—C9—C8	−0.8 (5)	C19—N2—C20—C25	12.8 (5)
C7—C8—C9—C1	−179.9 (4)	C25—C20—C21—C22	−0.3 (5)
C7—C8—C9—C10	−0.1 (5)	N2—C20—C21—C22	−179.7 (3)
C6—C5—C10—C9	0.0 (5)	C20—C21—C22—C23	0.0 (6)
C6—C5—C10—C4	179.0 (4)	C21—C22—C23—C24	0.1 (6)
C1—C9—C10—C5	179.8 (3)	C21—C22—C23—C26	−179.9 (4)
C8—C9—C10—C5	0.0 (4)	C22—C23—C24—C25	0.0 (5)
C1—C9—C10—C4	0.7 (4)	C26—C23—C24—C25	−179.9 (3)
C8—C9—C10—C4	−179.0 (3)	C21—C20—C25—C24	0.4 (5)
C3—C4—C10—C5	−177.6 (3)	N2—C20—C25—C24	179.8 (3)
C19—C4—C10—C5	3.9 (5)	C23—C24—C25—C20	−0.3 (5)
C3—C4—C10—C9	1.4 (5)	C29—N3—C28—O3	1.9 (13)
C19—C4—C10—C9	−177.1 (3)	C30—N3—C28—O3	−177.0 (13)
C12—N1—C11—O1	−0.4 (6)	C29—N3—C28—C27	176.7 (15)
C12—N1—C11—C1	178.8 (3)	C30—N3—C28—C27	−2.2 (17)
C2—C1—C11—O1	−90.8 (5)	C30'—N3'—C28'—O3'	5 (4)
C9—C1—C11—O1	87.5 (5)	C29'—N3'—C28'—O3'	176 (2)
C2—C1—C11—N1	89.9 (4)	C30'—N3'—C28'—C27'	−178 (4)
C9—C1—C11—N1	−91.8 (4)	C29'—N3'—C28'—C27'	−6 (3)
C11—N1—C12—C17	7.8 (5)	C34—N4—C32—O4	177.9 (12)
C11—N1—C12—C13	−172.1 (3)	C33—N4—C32—O4	−1.9 (17)
C17—C12—C13—C14	−0.5 (5)	C34—N4—C32—C31	3 (2)
N1—C12—C13—C14	179.3 (3)	C33—N4—C32—C31	−177 (2)
C12—C13—C14—C15	0.1 (5)	C34'—N4'—C32'—O4'	−2 (2)
C13—C14—C15—C16	−0.3 (5)	C33'—N4'—C32'—O4'	177 (2)
C13—C14—C15—C18	−177.9 (3)	C34'—N4'—C32'—C31'	−172 (2)
C14—C15—C16—C17	0.9 (5)	C33'—N4'—C32'—C31'	7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4	0.86	2.02	2.880 (15)	175
N2—H2N···O3ⁱ	0.86	1.99	2.821 (13)	162
C24—H24···O1ⁱⁱ	0.93	2.57	3.466 (5)	163
C17—H17···O1	0.93	2.33	2.911 (4)	120
C25—H25···O2	0.93	2.33	2.907 (4)	120

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₂N₂O₂·2C₄H₉NO
M_r	568.70
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	13.270 (3), 20.285 (4), 12.125 (3)
β (°)	101.021 (4)
V (Å³)	3203.7 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.24 × 0.22 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.982, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	16193, 5652, 2347
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.186, 1.00
No. of reflections	5652
No. of parameters	491
No. of restraints	166
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.18

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4	0.86	2.02	2.880 (15)	175
N2—H2N···O3ⁱ	0.86	1.99	2.821 (13)	162
C24—H24···O1ⁱⁱ	0.93	2.57	3.466 (5)	163
C17—H17···O1	0.93	2.33	2.911 (4)	120
C25—H25···O2	0.93	2.33	2.907 (4)	120

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

Acknowledgements

The authors thank the Centre for Testing and Analysis, Cheng Du Branch, Chinese Academy of Sciences, for analytical support.

References

Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fukuzumi, T., Tajiri, T., Tsukada, H. & Yoshida, J. (1994). Jpn Patent JP 06 298 919. Google Scholar
Jing, L.-H., Qin, D.-B., Gu, S.-J., Zhang, H.-X. & Lei, G. (2006a). Acta Cryst. C62, o561–o562. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Jing, L. H., Qin, D. B., Gu, S. J., Zhang, H. X. & Mao, Z. H. (2006b). Z. Kristallogr. New Cryst. Struct. 221, 200–202. CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tsukada, H., Tajiri, T., Fukuzumi, T. & Yoshida, J. (1994). Jpn Patent JP 06 298 918. Google Scholar

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Volume 64| Part 12| December 2008| Page o2379

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

N,N′-Bis(4-methyl­phen­yl)naphthalene-1,4-dicarboxamide N,N-di­methyl­acetamide disolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N,N′-Bis(4-methylphenyl)naphthalene-1,4-dicarboxamide N,N-dimethylacetamide disolvate