N,N′-Bis(4-chloro­phen­yl)naphthalene-1,4-dicarboxamide N,N-dimethyl­formamide disolvate

Jing, L.-H.

doi:10.1107/S1600536809034394

organic compounds

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Volume 65| Part 10| October 2009| Page o2414

doi:10.1107/S1600536809034394

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N,N′-Bis(4-chlorophenyl)naphthalene-1,4-dicarboxamide N,N-dimethylformamide 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 26 August 2009; accepted 27 August 2009; online 9 September 2009)

In the title compound, C₂₄H₁₆Cl₂N₂O₂·2C₃H₇NO, the two C=O groups adopt an anti orientation. The two amide groups are twisted away from the naphthalene ring system by 59.10 (4) and 68.22 (4)°. The crystal packing is stabilized by N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For the use of 1,4-naphthalenedicarboxylic acid derivatives in the preparation of polymers, see: Fukuzumi et al. (1994 ); Tsukada et al. (1994 ). For related structures, see: Jing (2008 ); Jing et al. (2006a ,b ).

Experimental

Crystal data

C₂₄H₁₆Cl₂N₂O₂·2C₃H₇NO
M_r = 581.48
Triclinic, $[P \overline 1]$
a = 12.040 (3) Å
b = 12.121 (3) Å
c = 12.295 (3) Å
α = 101.75°
β = 111.843 (3)°
γ = 110.833 (2)°
V = 1435.1 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 93 K
0.40 × 0.33 × 0.30 mm

Data collection

Rigaku SPIDER diffractometer
Absorption correction: none
11770 measured reflections
6317 independent reflections
5120 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.095
S = 1.00
6317 reflections
373 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4ⁱ	0.85 (2)	2.01 (2)	2.8536 (17)	173 (2)
N2—H2N⋯O3	0.89 (2)	2.02 (2)	2.9040 (17)	168 (2)
C23—H23⋯O4	0.95	2.39	3.3258 (19)	167
C2—H2⋯O3ⁱⁱ	0.95	2.54	3.4458 (19)	160
C6—H6⋯O2ⁱⁱⁱ	0.95	2.38	3.3214 (19)	169
C16—H16⋯O3ⁱ	0.95	2.54	3.3949 (19)	151
C21—H21⋯O1^iv	0.95	2.37	3.1719 (19)	142
Symmetry codes: (i) x+1, y, z+1; (ii) -x+1, -y+1, -z+1; (iii) -x+2, -y+2, -z+1; (iv) x, y+1, z.

Data collection: RAPID-AUTO (Rigaku, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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/S1600536809034394/ci2896sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809034394/ci2896Isup2.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 crystal structures of N,N'-bis(4-nitrophenyl)naphthalene-1,4-dicarboxamide dimethylsulfoxide disolvate (Jing et al., 2006a), N,N'-bis(2-methoxyphenyl)naphthalene-1,4-dicarboxamide (Jing et al., 2006b) and N,N'-bis(4-methylphenyl)-1,4-naphthalenedicarboxamide N,N-dimethylacetamide disolvate (Jing, 2008). We now report the crystal structure of the title compound.

Bond lengths and angles in the molecules are normal. The naphthalene ring system is planar, with a maximum deviation of 0.056 (1) Å for atom C2. Two C═O groups exhibit an anti orientation. 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/C18 planes form dihedral angles of 59.10 (4) and 68.22 (4)°, respectively, with the C1-C10 plane. The O1/N1/C1/C11 and C12—C17 planes are inclined at an angle of 12.15 (8)° while the O2/N2/C4/C18 and C19—C24 planes make a dihedral angle of 11.22 (9)°. The crystal packing is stabilized by N—H···O and C—H···O hydrogen bonds (Table 1).

Related literature top

For the use of 1,4-naphthalenedicarboxylic acid derivatives in the preparation of polymers, see: Fukuzumi et al. (1994); Tsukada et al. (1994). For related structures, see: Jing (2008); 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-Chloroaniline (4 mmol) in tetrahydrofuran (20 ml) was added to the yellow solid and boiled under reflux for 6 h. The solution was then cooled to ambient temperature and filtered to remove the tetrahydrofuran. The precipitate obtained was dissolved in dimethylformamide and allowed to stand for one month at ambient temperature, after which time colourless single crystals suitable for X-ray diffraction were obtained.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); 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, showing 30% probability displacement ellipsoids and the atomic numbering.

N,N'-Bis(4-chlorophenyl)naphthalene-1,4-dicarboxamide N,N-dimethylformamide disolvate top

Crystal data top

C₂₄H₁₆Cl₂N₂O₂·2C₃H₇NO	Z = 2
M_r = 581.48	F(000) = 608
Triclinic, P1	D_x = 1.346 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.040 (3) Å	Cell parameters from 4703 reflections
b = 12.121 (3) Å	θ = 3.2–27.5°
c = 12.295 (3) Å	µ = 0.27 mm⁻¹
α = 101.75°	T = 93 K
β = 111.843 (3)°	Block, colourless
γ = 110.833 (2)°	0.40 × 0.33 × 0.30 mm
V = 1435.1 (6) Å³

Data collection top

Rigaku SPIDER diffractometer	5120 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.021
Graphite monochromator	θ_max = 27.5°, θ_min = 3.2°
ω scans	h = −14→14
11770 measured reflections	k = −15→15
6317 independent reflections	l = −15→15

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0495P)² + 0.26P] where P = (F_o² + 2F_c²)/3
6317 reflections	(Δ/σ)_max = 0.001
373 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₄H₁₆Cl₂N₂O₂·2C₃H₇NO	γ = 110.833 (2)°
M_r = 581.48	V = 1435.1 (6) Å³
Triclinic, P1	Z = 2
a = 12.040 (3) Å	Mo Kα radiation
b = 12.121 (3) Å	µ = 0.27 mm⁻¹
c = 12.295 (3) Å	T = 93 K
α = 101.75°	0.40 × 0.33 × 0.30 mm
β = 111.843 (3)°

Data collection top

Rigaku SPIDER diffractometer	5120 reflections with I > 2σ(I)
11770 measured reflections	R_int = 0.021
6317 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.35 e Å⁻³
6317 reflections	Δρ_min = −0.22 e Å⁻³
373 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
Cl1	1.14954 (4)	0.24083 (4)	1.06116 (4)	0.02618 (10)
Cl2	0.34115 (4)	1.10782 (4)	0.16440 (4)	0.02949 (11)
O1	0.72486 (10)	0.35489 (10)	0.60000 (10)	0.0254 (2)
O2	0.78897 (10)	0.97633 (10)	0.58937 (10)	0.0223 (2)
N1	0.93824 (12)	0.51036 (12)	0.75515 (11)	0.0166 (3)
N2	0.58949 (12)	0.82237 (12)	0.41155 (11)	0.0185 (3)
C1	0.79112 (14)	0.56799 (13)	0.61081 (12)	0.0152 (3)
C2	0.68071 (14)	0.57861 (13)	0.60897 (13)	0.0175 (3)
H2	0.6230	0.5214	0.6305	0.021*
C3	0.65240 (14)	0.67394 (13)	0.57528 (13)	0.0172 (3)
H3	0.5759	0.6806	0.5746	0.021*
C4	0.73406 (14)	0.75669 (13)	0.54364 (12)	0.0158 (3)
C5	0.92703 (15)	0.82315 (14)	0.49705 (14)	0.0204 (3)
H5	0.9085	0.8876	0.4746	0.024*
C6	1.03101 (16)	0.80760 (15)	0.48905 (15)	0.0239 (3)
H6	1.0837	0.8606	0.4607	0.029*
C7	1.06006 (16)	0.71245 (15)	0.52307 (14)	0.0232 (3)
H7	1.1325	0.7018	0.5176	0.028*
C8	0.98458 (15)	0.63599 (14)	0.56367 (13)	0.0193 (3)
H8	1.0060	0.5731	0.5869	0.023*
C9	0.87465 (14)	0.64829 (13)	0.57208 (12)	0.0151 (3)
C10	0.84593 (14)	0.74473 (13)	0.53832 (12)	0.0157 (3)
C11	0.81469 (14)	0.46640 (13)	0.65323 (13)	0.0159 (3)
C12	0.98484 (14)	0.44042 (13)	0.82256 (13)	0.0153 (3)
C13	0.91798 (15)	0.30732 (13)	0.77869 (13)	0.0187 (3)
H13	0.8375	0.2585	0.6987	0.022*
C14	0.96930 (15)	0.24596 (14)	0.85217 (14)	0.0203 (3)
H14	0.9242	0.1552	0.8226	0.024*
C15	1.08613 (15)	0.31781 (14)	0.96829 (13)	0.0181 (3)
C16	1.15477 (14)	0.45050 (14)	1.01369 (13)	0.0183 (3)
H16	1.2352	0.4988	1.0937	0.022*
C17	1.10346 (14)	0.51115 (14)	0.93975 (13)	0.0177 (3)
H17	1.1496	0.6019	0.9693	0.021*
C18	0.70864 (14)	0.86425 (13)	0.51829 (13)	0.0167 (3)
C19	0.53522 (14)	0.89601 (13)	0.35801 (13)	0.0164 (3)
C20	0.58492 (14)	1.02652 (13)	0.42169 (14)	0.0180 (3)
H20	0.6596	1.0709	0.5056	0.022*
C21	0.52446 (15)	1.09143 (14)	0.36147 (13)	0.0190 (3)
H21	0.5579	1.1804	0.4038	0.023*
C22	0.41559 (15)	1.02545 (14)	0.23974 (13)	0.0184 (3)
C23	0.36372 (15)	0.89561 (14)	0.17557 (14)	0.0211 (3)
H23	0.2882	0.8515	0.0921	0.025*
C24	0.42413 (15)	0.83144 (14)	0.23555 (14)	0.0209 (3)
H24	0.3895	0.7423	0.1928	0.025*
O3	0.48112 (11)	0.56240 (10)	0.23871 (10)	0.0235 (2)
O4	0.12745 (11)	0.77715 (10)	−0.12739 (10)	0.0301 (3)
N3	0.62413 (14)	0.49392 (13)	0.20677 (14)	0.0286 (3)
N4	0.19877 (13)	0.95703 (12)	−0.16672 (12)	0.0244 (3)
C25	0.53141 (16)	0.48995 (15)	0.24215 (15)	0.0254 (3)
H25	0.5014	0.4255	0.2728	0.030*
C26	0.6798 (2)	0.4056 (2)	0.2165 (2)	0.0498 (5)
H26A	0.6433	0.3516	0.2570	0.060*
H26B	0.7790	0.4541	0.2676	0.060*
H26C	0.6544	0.3516	0.1313	0.060*
C27	0.6761 (2)	0.58983 (19)	0.1596 (2)	0.0437 (5)
H27A	0.6471	0.5480	0.0697	0.052*
H27B	0.7756	0.6359	0.2084	0.052*
H27C	0.6406	0.6504	0.1690	0.052*
C28	0.11021 (16)	0.86429 (15)	−0.15544 (14)	0.0246 (3)
H28	0.0271	0.8645	−0.1699	0.030*
C29	0.1742 (2)	1.05877 (17)	−0.19713 (17)	0.0386 (4)
H29A	0.0801	1.0386	−0.2202	0.046*
H29B	0.1897	1.0665	−0.2687	0.046*
H29C	0.2363	1.1398	−0.1230	0.046*
C30	0.32963 (19)	0.96522 (19)	−0.14314 (19)	0.0411 (5)
H30A	0.4025	1.0433	−0.0689	0.049*
H30B	0.3412	0.9675	−0.2176	0.049*
H30C	0.3334	0.8903	−0.1271	0.049*
H1N	0.9893 (17)	0.5908 (17)	0.7908 (16)	0.024 (4)*
H2N	0.5477 (18)	0.7389 (19)	0.3633 (18)	0.037 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0315 (2)	0.0296 (2)	0.02474 (19)	0.02073 (17)	0.01110 (17)	0.01733 (16)
Cl2	0.0385 (2)	0.0270 (2)	0.02280 (19)	0.02399 (18)	0.00642 (17)	0.01041 (15)
O1	0.0206 (5)	0.0156 (5)	0.0267 (6)	0.0062 (4)	0.0015 (5)	0.0073 (4)
O2	0.0198 (5)	0.0163 (5)	0.0216 (5)	0.0068 (4)	0.0036 (4)	0.0067 (4)
N1	0.0161 (6)	0.0126 (6)	0.0166 (6)	0.0056 (5)	0.0048 (5)	0.0057 (5)
N2	0.0186 (6)	0.0138 (6)	0.0178 (6)	0.0082 (5)	0.0034 (5)	0.0058 (5)
C1	0.0171 (7)	0.0143 (6)	0.0116 (6)	0.0072 (5)	0.0048 (6)	0.0049 (5)
C2	0.0183 (7)	0.0165 (7)	0.0167 (7)	0.0069 (6)	0.0082 (6)	0.0077 (5)
C3	0.0153 (7)	0.0188 (7)	0.0176 (7)	0.0090 (6)	0.0073 (6)	0.0074 (6)
C4	0.0164 (7)	0.0159 (7)	0.0120 (6)	0.0081 (6)	0.0040 (6)	0.0049 (5)
C5	0.0239 (8)	0.0190 (7)	0.0210 (7)	0.0105 (6)	0.0113 (6)	0.0115 (6)
C6	0.0274 (8)	0.0242 (8)	0.0264 (8)	0.0112 (7)	0.0182 (7)	0.0137 (6)
C7	0.0239 (8)	0.0254 (8)	0.0263 (8)	0.0137 (7)	0.0160 (7)	0.0099 (6)
C8	0.0232 (8)	0.0198 (7)	0.0183 (7)	0.0125 (6)	0.0108 (6)	0.0080 (6)
C9	0.0161 (7)	0.0149 (6)	0.0111 (6)	0.0067 (5)	0.0049 (6)	0.0037 (5)
C10	0.0171 (7)	0.0155 (7)	0.0124 (6)	0.0072 (6)	0.0057 (6)	0.0056 (5)
C11	0.0175 (7)	0.0177 (7)	0.0142 (6)	0.0093 (6)	0.0079 (6)	0.0073 (5)
C12	0.0179 (7)	0.0175 (7)	0.0159 (6)	0.0104 (6)	0.0101 (6)	0.0091 (5)
C13	0.0187 (7)	0.0167 (7)	0.0158 (7)	0.0074 (6)	0.0052 (6)	0.0055 (5)
C14	0.0230 (8)	0.0175 (7)	0.0215 (7)	0.0107 (6)	0.0101 (6)	0.0089 (6)
C15	0.0206 (7)	0.0247 (8)	0.0196 (7)	0.0160 (6)	0.0119 (6)	0.0141 (6)
C16	0.0170 (7)	0.0231 (7)	0.0157 (7)	0.0109 (6)	0.0073 (6)	0.0077 (6)
C17	0.0169 (7)	0.0161 (7)	0.0189 (7)	0.0076 (6)	0.0077 (6)	0.0067 (5)
C18	0.0168 (7)	0.0188 (7)	0.0167 (7)	0.0088 (6)	0.0087 (6)	0.0090 (5)
C19	0.0155 (7)	0.0169 (7)	0.0187 (7)	0.0086 (6)	0.0081 (6)	0.0092 (6)
C20	0.0180 (7)	0.0175 (7)	0.0169 (7)	0.0088 (6)	0.0071 (6)	0.0057 (5)
C21	0.0225 (8)	0.0170 (7)	0.0197 (7)	0.0118 (6)	0.0102 (6)	0.0069 (6)
C22	0.0207 (7)	0.0212 (7)	0.0193 (7)	0.0147 (6)	0.0092 (6)	0.0108 (6)
C23	0.0181 (7)	0.0204 (7)	0.0184 (7)	0.0093 (6)	0.0032 (6)	0.0067 (6)
C24	0.0208 (8)	0.0141 (7)	0.0209 (7)	0.0076 (6)	0.0048 (6)	0.0056 (6)
O3	0.0238 (6)	0.0207 (5)	0.0253 (6)	0.0115 (5)	0.0114 (5)	0.0072 (4)
O4	0.0312 (6)	0.0197 (6)	0.0207 (5)	0.0045 (5)	0.0014 (5)	0.0093 (4)
N3	0.0289 (8)	0.0274 (7)	0.0382 (8)	0.0157 (6)	0.0219 (7)	0.0135 (6)
N4	0.0322 (7)	0.0215 (7)	0.0198 (6)	0.0118 (6)	0.0130 (6)	0.0095 (5)
C25	0.0294 (9)	0.0227 (8)	0.0293 (8)	0.0133 (7)	0.0175 (7)	0.0117 (7)
C26	0.0552 (13)	0.0498 (13)	0.0763 (16)	0.0392 (11)	0.0446 (12)	0.0316 (12)
C27	0.0473 (12)	0.0422 (11)	0.0649 (14)	0.0232 (9)	0.0431 (11)	0.0289 (10)
C28	0.0267 (8)	0.0238 (8)	0.0165 (7)	0.0089 (7)	0.0070 (6)	0.0077 (6)
C29	0.0612 (12)	0.0243 (9)	0.0314 (9)	0.0197 (9)	0.0220 (9)	0.0151 (7)
C30	0.0397 (11)	0.0399 (11)	0.0466 (11)	0.0152 (9)	0.0266 (10)	0.0176 (9)

Geometric parameters (Å, º) top

Cl1—C15	1.7462 (14)	C16—C17	1.3877 (19)
Cl2—C22	1.7473 (14)	C16—H16	0.95
O1—C11	1.2240 (17)	C17—H17	0.95
O2—C18	1.2238 (17)	C19—C24	1.395 (2)
N1—C11	1.3580 (18)	C19—C20	1.3954 (19)
N1—C12	1.4138 (17)	C20—C21	1.3930 (19)
N1—H1N	0.849 (18)	C20—H20	0.95
N2—C18	1.3594 (18)	C21—C22	1.380 (2)
N2—C19	1.4110 (17)	C21—H21	0.95
N2—H2N	0.895 (19)	C22—C23	1.385 (2)
C1—C2	1.373 (2)	C23—C24	1.3837 (19)
C1—C9	1.4264 (19)	C23—H23	0.95
C1—C11	1.5062 (18)	C24—H24	0.95
C2—C3	1.4117 (19)	O3—C25	1.2304 (18)
C2—H2	0.95	O4—C28	1.2363 (19)
C3—C4	1.366 (2)	N3—C25	1.330 (2)
C3—H3	0.95	N3—C27	1.451 (2)
C4—C10	1.428 (2)	N3—C26	1.453 (2)
C4—C18	1.5062 (19)	N4—C28	1.319 (2)
C5—C6	1.366 (2)	N4—C29	1.454 (2)
C5—C10	1.421 (2)	N4—C30	1.454 (2)
C5—H5	0.95	C25—H25	0.95
C6—C7	1.415 (2)	C26—H26A	0.98
C6—H6	0.95	C26—H26B	0.98
C7—C8	1.364 (2)	C26—H26C	0.98
C7—H7	0.95	C27—H27A	0.98
C8—C9	1.421 (2)	C27—H27B	0.98
C8—H8	0.95	C27—H27C	0.98
C9—C10	1.4271 (19)	C28—H28	0.95
C12—C13	1.3930 (19)	C29—H29A	0.98
C12—C17	1.3949 (19)	C29—H29B	0.98
C13—C14	1.3914 (19)	C29—H29C	0.98
C13—H13	0.95	C30—H30A	0.98
C14—C15	1.380 (2)	C30—H30B	0.98
C14—H14	0.95	C30—H30C	0.98
C15—C16	1.388 (2)

C11—N1—C12	127.53 (12)	O2—C18—N2	125.43 (13)
C11—N1—H1N	117.1 (11)	O2—C18—C4	121.68 (12)
C12—N1—H1N	114.5 (12)	N2—C18—C4	112.89 (12)
C18—N2—C19	128.18 (12)	C24—C19—C20	119.68 (13)
C18—N2—H2N	115.0 (12)	C24—C19—N2	116.70 (12)
C19—N2—H2N	116.0 (12)	C20—C19—N2	123.61 (13)
C2—C1—C9	120.61 (13)	C21—C20—C19	119.64 (13)
C2—C1—C11	115.86 (12)	C21—C20—H20	120.2
C9—C1—C11	123.53 (12)	C19—C20—H20	120.2
C1—C2—C3	120.43 (13)	C22—C21—C20	119.46 (13)
C1—C2—H2	119.8	C22—C21—H21	120.3
C3—C2—H2	119.8	C20—C21—H21	120.3
C4—C3—C2	120.57 (13)	C21—C22—C23	121.76 (13)
C4—C3—H3	119.7	C21—C22—Cl2	119.18 (11)
C2—C3—H3	119.7	C23—C22—Cl2	119.05 (11)
C3—C4—C10	120.67 (13)	C24—C23—C22	118.64 (13)
C3—C4—C18	119.65 (12)	C24—C23—H23	120.7
C10—C4—C18	119.65 (12)	C22—C23—H23	120.7
C6—C5—C10	121.27 (14)	C23—C24—C19	120.81 (13)
C6—C5—H5	119.4	C23—C24—H24	119.6
C10—C5—H5	119.4	C19—C24—H24	119.6
C5—C6—C7	119.86 (14)	C25—N3—C27	120.68 (14)
C5—C6—H6	120.1	C25—N3—C26	121.89 (15)
C7—C6—H6	120.1	C27—N3—C26	117.41 (15)
C8—C7—C6	120.34 (14)	C28—N4—C29	122.37 (15)
C8—C7—H7	119.8	C28—N4—C30	120.96 (14)
C6—C7—H7	119.8	C29—N4—C30	116.61 (15)
C7—C8—C9	121.50 (14)	O3—C25—N3	125.73 (16)
C7—C8—H8	119.2	O3—C25—H25	117.1
C9—C8—H8	119.2	N3—C25—H25	117.1
C8—C9—C1	123.18 (13)	N3—C26—H26A	109.5
C8—C9—C10	118.07 (13)	N3—C26—H26B	109.5
C1—C9—C10	118.74 (12)	H26A—C26—H26B	109.5
C5—C10—C9	118.95 (13)	N3—C26—H26C	109.5
C5—C10—C4	122.19 (13)	H26A—C26—H26C	109.5
C9—C10—C4	118.83 (13)	H26B—C26—H26C	109.5
O1—C11—N1	124.73 (13)	N3—C27—H27A	109.5
O1—C11—C1	120.55 (12)	N3—C27—H27B	109.5
N1—C11—C1	114.67 (12)	H27A—C27—H27B	109.5
C13—C12—C17	119.60 (13)	N3—C27—H27C	109.5
C13—C12—N1	123.54 (13)	H27A—C27—H27C	109.5
C17—C12—N1	116.86 (12)	H27B—C27—H27C	109.5
C14—C13—C12	119.91 (13)	O4—C28—N4	124.81 (16)
C14—C13—H13	120.0	O4—C28—H28	117.6
C12—C13—H13	120.0	N4—C28—H28	117.6
C15—C14—C13	119.55 (14)	N4—C29—H29A	109.5
C15—C14—H14	120.2	N4—C29—H29B	109.5
C13—C14—H14	120.2	H29A—C29—H29B	109.5
C14—C15—C16	121.55 (13)	N4—C29—H29C	109.5
C14—C15—Cl1	119.53 (11)	H29A—C29—H29C	109.5
C16—C15—Cl1	118.92 (11)	H29B—C29—H29C	109.5
C17—C16—C15	118.65 (13)	N4—C30—H30A	109.5
C17—C16—H16	120.7	N4—C30—H30B	109.5
C15—C16—H16	120.7	H30A—C30—H30B	109.5
C16—C17—C12	120.75 (13)	N4—C30—H30C	109.5
C16—C17—H17	119.6	H30A—C30—H30C	109.5
C12—C17—H17	119.6	H30B—C30—H30C	109.5

C9—C1—C2—C3	−3.5 (2)	C17—C12—C13—C14	0.4 (2)
C11—C1—C2—C3	177.63 (12)	N1—C12—C13—C14	−178.74 (13)
C1—C2—C3—C4	0.2 (2)	C12—C13—C14—C15	0.1 (2)
C2—C3—C4—C10	2.9 (2)	C13—C14—C15—C16	−0.4 (2)
C2—C3—C4—C18	−175.08 (12)	C13—C14—C15—Cl1	179.37 (11)
C10—C5—C6—C7	−0.4 (2)	C14—C15—C16—C17	0.1 (2)
C5—C6—C7—C8	0.1 (2)	Cl1—C15—C16—C17	−179.65 (10)
C6—C7—C8—C9	0.6 (2)	C15—C16—C17—C12	0.4 (2)
C7—C8—C9—C1	178.28 (14)	C13—C12—C17—C16	−0.7 (2)
C7—C8—C9—C10	−0.8 (2)	N1—C12—C17—C16	178.50 (13)
C2—C1—C9—C8	−175.58 (13)	C19—N2—C18—O2	2.1 (2)
C11—C1—C9—C8	3.2 (2)	C19—N2—C18—C4	−178.44 (13)
C2—C1—C9—C10	3.53 (19)	C3—C4—C18—O2	112.28 (16)
C11—C1—C9—C10	−177.64 (12)	C10—C4—C18—O2	−65.73 (18)
C6—C5—C10—C9	0.1 (2)	C3—C4—C18—N2	−67.17 (17)
C6—C5—C10—C4	−178.02 (13)	C10—C4—C18—N2	114.83 (14)
C8—C9—C10—C5	0.50 (19)	C18—N2—C19—C24	168.17 (14)
C1—C9—C10—C5	−178.66 (12)	C18—N2—C19—C20	−13.1 (2)
C8—C9—C10—C4	178.70 (12)	C24—C19—C20—C21	−1.0 (2)
C1—C9—C10—C4	−0.46 (19)	N2—C19—C20—C21	−179.70 (13)
C3—C4—C10—C5	175.41 (13)	C19—C20—C21—C22	0.4 (2)
C18—C4—C10—C5	−6.6 (2)	C20—C21—C22—C23	0.4 (2)
C3—C4—C10—C9	−2.72 (19)	C20—C21—C22—Cl2	−179.51 (11)
C18—C4—C10—C9	175.26 (12)	C21—C22—C23—C24	−0.6 (2)
C12—N1—C11—O1	−3.3 (2)	Cl2—C22—C23—C24	179.40 (12)
C12—N1—C11—C1	174.14 (12)	C22—C23—C24—C19	−0.2 (2)
C2—C1—C11—O1	55.39 (18)	C20—C19—C24—C23	0.9 (2)
C9—C1—C11—O1	−123.49 (16)	N2—C19—C24—C23	179.69 (13)
C2—C1—C11—N1	−122.19 (14)	C27—N3—C25—O3	0.4 (3)
C9—C1—C11—N1	58.93 (17)	C26—N3—C25—O3	178.82 (17)
C11—N1—C12—C13	12.7 (2)	C29—N4—C28—O4	−178.55 (14)
C11—N1—C12—C17	−166.47 (13)	C30—N4—C28—O4	−1.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O3	0.89 (2)	2.02 (2)	2.9040 (17)	168 (2)
C23—H23···O4	0.95	2.39	3.3258 (19)	167
N1—H1N···O4ⁱ	0.85 (2)	2.01 (2)	2.8536 (17)	173 (2)
C2—H2···O3ⁱⁱ	0.95	2.54	3.4458 (19)	160
C6—H6···O2ⁱⁱⁱ	0.95	2.38	3.3214 (19)	169
C16—H16···O3ⁱ	0.95	2.54	3.3949 (19)	151
C21—H21···O1^iv	0.95	2.37	3.1719 (19)	142

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

Experimental details

Crystal data
Chemical formula	C₂₄H₁₆Cl₂N₂O₂·2C₃H₇NO
M_r	581.48
Crystal system, space group	Triclinic, P1
Temperature (K)	93
a, b, c (Å)	12.040 (3), 12.121 (3), 12.295 (3)
α, β, γ (°)	101.75, 111.843 (3), 110.833 (2)
V (Å³)	1435.1 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.40 × 0.33 × 0.30

Data collection
Diffractometer	Rigaku SPIDER diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11770, 6317, 5120
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.095, 1.00
No. of reflections	6317
No. of parameters	373
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.22

Computer programs: RAPID-AUTO (Rigaku, 2004), 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
N2—H2N···O3	0.89 (2)	2.02 (2)	2.9040 (17)	168 (2)
C23—H23···O4	0.95	2.39	3.3258 (19)	167
N1—H1N···O4ⁱ	0.85 (2)	2.01 (2)	2.8536 (17)	173 (2)
C2—H2···O3ⁱⁱ	0.95	2.54	3.4458 (19)	160
C6—H6···O2ⁱⁱⁱ	0.95	2.38	3.3214 (19)	169
C16—H16···O3ⁱ	0.95	2.54	3.3949 (19)	151
C21—H21···O1^iv	0.95	2.37	3.1719 (19)	142

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

Acknowledgements

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

References

Fukuzumi, T., Tajiri, T., Tsukada, H. & Yoshida, J. (1994). Jpn Patent JP 06 298 919. Google Scholar
Jing, L.-H. (2008). Acta Cryst. E64, o2379. Web of Science CSD CrossRef IUCr Journals 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
Rigaku (2004). RAPID-AUTO. 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
Tsukada, H., Tajiri, T., Fukuzumi, T. & Yoshida, J. (1994). Jpn Patent JP 06 298 918. Google Scholar

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Volume 65| Part 10| October 2009| Page o2414

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

N,N′-Bis(4-chloro­phen­yl)naphthalene-1,4-dicarboxamide N,N-di­methyl­formamide disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N,N′-Bis(4-chlorophenyl)naphthalene-1,4-dicarboxamide N,N-dimethylformamide disolvate