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

Jing, L.-H.

doi:10.1107/S1600536809051447

organic compounds

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Volume 66| Part 1| January 2010| Page o27

doi:10.1107/S1600536809051447

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N,N′-Bis(4-bromophenyl)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: jhrkk20060220@yahoo.com.cn

(Received 17 November 2009; accepted 29 November 2009; online 4 December 2009)

The title compound, C₂₄H₁₆Br₂N₂O₂·2C₄H₉NO, crystallizes in an anti C=O orientation. The two amide groups are twisted away from the naphthalene ring system by 62.67 (8) and 75.93 (7)°. The crystal packing is stabilized by N—H⋯O and C—H⋯O hydrogen bonds. Each of the dimethylacetamide solvent molecules is disordered over two positions, with occupancy ratios of 0.556 (7):0.444 (7) and 0.654 (7):0.346 (7).

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 the crystal structure of the 4-methylphenyl analog, see: Jing (2008 ).

Experimental

Crystal data

C₂₄H₁₆Br₂N₂O₂·2C₄H₉NO
M_r = 698.45
Triclinic, $[P \overline 1]$
a = 10.4589 (9) Å
b = 12.4485 (5) Å
c = 12.8439 (11) Å
α = 90.775 (2)°
β = 111.370 (4)°
γ = 92.944 (2)°
V = 1554.3 (2) Å³
Z = 2
Mo Kα radiation
μ = 2.65 mm⁻¹
T = 93 K
0.47 × 0.33 × 0.17 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.364, T_max = 0.637
12655 measured reflections
6836 independent reflections
5420 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.065
S = 0.95
6836 reflections
509 parameters
64 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.73 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4	0.84 (2)	2.03 (3)	2.865 (13)	170 (2)
N2—H2N⋯O3′ⁱ	0.81 (2)	2.00 (3)	2.797 (13)	171 (2)
C2—H2⋯O1ⁱ	0.95	2.50	3.423 (2)	163
C6—H6⋯O2ⁱⁱ	0.95	2.49	3.426 (2)	169
C14—H14⋯O4ⁱⁱⁱ	0.95	2.55	3.48 (2)	167
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+2, -z+1; (iii) -x+1, -y+1, -z+2.

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809051447/ci2967sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809051447/ci2967Isup2.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, the author has reported the crystal structure of N,N'-bis(4-methylphenyl)-1,4-naphthalenedicarboxamide N,N-dimethylacetamide disolvate (Jing, 2008). The crystal structure of the title compound is now reported.

The naphthalene ring system is planar, with a maximum deviation of 0.030 (3) Å for atom C3. The 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 62.67 (8) and 75.93 (7)°, respectively, with the C1–C4/C9/C10 plane. The O1/N1/C1/C11 and C12–C17 planes are inclined at an angle of 16.21 (4)° while the O2/N2/C4/C18 and C19–C24 planes make a dihedral angle of 7.42 (3)°. 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 the crystal structure of the 4-methylphenyl analog, see: Jing (2008).

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 by reduced pressure and a yellow solid was obtained. p-Bromoaniline (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: 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: 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 50% probability level. All disorder components are shown. H atoms have been omitted for clarity.

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

Crystal data top

C₂₄H₁₆Br₂N₂O₂·2C₄H₉NO	Z = 2
M_r = 698.45	F(000) = 712
Triclinic, P1	D_x = 1.492 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.4589 (9) Å	Cell parameters from 4940 reflections
b = 12.4485 (5) Å	θ = 3.2–27.5°
c = 12.8439 (11) Å	µ = 2.65 mm⁻¹
α = 90.775 (2)°	T = 93 K
β = 111.370 (4)°	Prism, colourless
γ = 92.944 (2)°	0.47 × 0.33 × 0.17 mm
V = 1554.3 (2) Å³

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	6836 independent reflections
Radiation source: Rotating Anode	5420 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
ω scans	h = −11→13
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −15→16
T_min = 0.364, T_max = 0.637	l = −16→14
12655 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ²(F_o²) + (0.0312P)²] where P = (F_o² + 2F_c²)/3
6836 reflections	(Δ/σ)_max = 0.001
509 parameters	Δρ_max = 0.35 e Å⁻³
64 restraints	Δρ_min = −0.73 e Å⁻³

Crystal data top

C₂₄H₁₆Br₂N₂O₂·2C₄H₉NO	γ = 92.944 (2)°
M_r = 698.45	V = 1554.3 (2) Å³
Triclinic, P1	Z = 2
a = 10.4589 (9) Å	Mo Kα radiation
b = 12.4485 (5) Å	µ = 2.65 mm⁻¹
c = 12.8439 (11) Å	T = 93 K
α = 90.775 (2)°	0.47 × 0.33 × 0.17 mm
β = 111.370 (4)°

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	6836 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	5420 reflections with I > 2σ(I)
T_min = 0.364, T_max = 0.637	R_int = 0.024
12655 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	64 restraints
wR(F²) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	Δρ_max = 0.35 e Å⁻³
6836 reflections	Δρ_min = −0.73 e Å⁻³
509 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)
Br1	0.53236 (2)	0.112534 (16)	0.932514 (17)	0.02903 (7)
Br2	0.22415 (2)	1.394801 (16)	0.057404 (18)	0.03060 (7)
O1	0.32331 (13)	0.45436 (10)	0.48313 (11)	0.0177 (3)
O2	0.31551 (13)	1.04379 (10)	0.50572 (11)	0.0191 (3)
N1	0.34837 (17)	0.50996 (13)	0.66106 (14)	0.0168 (3)
H1N	0.348 (2)	0.5650 (19)	0.700 (2)	0.039 (7)*
N2	0.23601 (17)	0.99105 (13)	0.32026 (14)	0.0189 (4)
H2N	0.203 (2)	0.9395 (17)	0.2781 (19)	0.024 (6)*
C1	0.30036 (18)	0.63948 (14)	0.51685 (15)	0.0143 (4)
C2	0.39398 (19)	0.68975 (15)	0.47878 (16)	0.0171 (4)
H2	0.4670	0.6508	0.4729	0.021*
C3	0.38368 (19)	0.79752 (15)	0.44845 (16)	0.0172 (4)
H3	0.4495	0.8307	0.4222	0.021*
C4	0.27922 (18)	0.85564 (14)	0.45630 (15)	0.0145 (4)
C5	0.06363 (19)	0.86155 (15)	0.49518 (16)	0.0170 (4)
H5	0.0559	0.9348	0.4750	0.020*
C6	−0.03434 (19)	0.81135 (15)	0.52719 (16)	0.0183 (4)
H6	−0.1095	0.8499	0.5291	0.022*
C7	−0.02522 (19)	0.70304 (15)	0.55738 (16)	0.0178 (4)
H7	−0.0940	0.6690	0.5798	0.021*
C8	0.08240 (18)	0.64638 (15)	0.55463 (16)	0.0159 (4)
H8	0.0872	0.5731	0.5746	0.019*
C9	0.18715 (18)	0.69610 (14)	0.52222 (15)	0.0130 (4)
C10	0.17723 (18)	0.80569 (14)	0.49159 (15)	0.0136 (4)
C11	0.32325 (18)	0.52500 (14)	0.55106 (16)	0.0144 (4)
C12	0.38661 (19)	0.41416 (14)	0.71995 (16)	0.0153 (4)
C13	0.44442 (19)	0.42461 (15)	0.83616 (16)	0.0184 (4)
H13	0.4552	0.4937	0.8717	0.022*
C14	0.48654 (19)	0.33506 (15)	0.90073 (16)	0.0187 (4)
H14	0.5262	0.3420	0.9800	0.022*
C15	0.46910 (19)	0.23536 (15)	0.84642 (16)	0.0175 (4)
C16	0.40962 (18)	0.22272 (14)	0.73121 (16)	0.0158 (4)
H16	0.3972	0.1532	0.6962	0.019*
C17	0.36833 (18)	0.31242 (14)	0.66737 (16)	0.0145 (4)
H17	0.3278	0.3048	0.5882	0.017*
C18	0.27844 (18)	0.97352 (14)	0.43114 (16)	0.0147 (4)
C19	0.23255 (19)	1.08886 (15)	0.26482 (16)	0.0162 (4)
C20	0.27827 (18)	1.18916 (15)	0.31961 (16)	0.0169 (4)
H20	0.3117	1.1949	0.3990	0.020*
C21	0.27480 (19)	1.28043 (15)	0.25775 (16)	0.0180 (4)
H21	0.3053	1.3490	0.2944	0.022*
C22	0.2264 (2)	1.27038 (15)	0.14216 (17)	0.0195 (4)
C23	0.1782 (2)	1.17201 (15)	0.08598 (17)	0.0236 (5)
H23	0.1433	1.1669	0.0066	0.028*
C24	0.1820 (2)	1.08126 (15)	0.14807 (17)	0.0222 (4)
H24	0.1500	1.0132	0.1108	0.027*
O3	0.9394 (16)	0.1698 (9)	0.8232 (17)	0.021 (2)	0.444 (7)
N3	0.8990 (5)	0.3438 (4)	0.7831 (4)	0.0226 (14)	0.444 (7)
C25	1.0986 (17)	0.2599 (10)	0.7668 (15)	0.025 (2)	0.444 (7)
H25A	1.1649	0.3154	0.8142	0.030*	0.444 (7)
H25B	1.0762	0.2764	0.6879	0.030*	0.444 (7)
H25C	1.1387	0.1896	0.7810	0.030*	0.444 (7)
C26	0.9712 (6)	0.2573 (4)	0.7930 (4)	0.0205 (15)	0.444 (7)
C27	0.9413 (14)	0.4520 (8)	0.7573 (15)	0.024 (2)	0.444 (7)
H27A	0.9882	0.4942	0.8271	0.029*	0.444 (7)
H27B	0.8599	0.4881	0.7108	0.029*	0.444 (7)
H27C	1.0041	0.4454	0.7168	0.029*	0.444 (7)
C28	0.7799 (19)	0.3420 (14)	0.8162 (18)	0.024 (3)	0.444 (7)
H28A	0.7246	0.2743	0.7893	0.029*	0.444 (7)
H28B	0.7242	0.4026	0.7837	0.029*	0.444 (7)
H28C	0.8107	0.3478	0.8980	0.029*	0.444 (7)
O3'	0.9084 (13)	0.1781 (7)	0.8283 (14)	0.0227 (19)	0.556 (7)
N3'	0.9840 (5)	0.3352 (3)	0.7788 (3)	0.0245 (12)	0.556 (7)
C25'	0.7828 (18)	0.3251 (12)	0.8320 (16)	0.040 (4)	0.556 (7)
H25D	0.7252	0.2693	0.8500	0.048*	0.556 (7)
H25E	0.7272	0.3612	0.7646	0.048*	0.556 (7)
H25F	0.8198	0.3778	0.8946	0.048*	0.556 (7)
C26'	0.8982 (4)	0.2748 (4)	0.8120 (3)	0.0197 (12)	0.556 (7)
C27'	0.9802 (11)	0.4515 (7)	0.7669 (13)	0.036 (3)	0.556 (7)
H27D	0.9253	0.4673	0.6894	0.043*	0.556 (7)
H27E	1.0740	0.4832	0.7864	0.043*	0.556 (7)
H27F	0.9387	0.4821	0.8169	0.043*	0.556 (7)
C28'	1.0974 (13)	0.2903 (8)	0.7562 (12)	0.034 (3)	0.556 (7)
H28D	1.1842	0.3113	0.8174	0.041*	0.556 (7)
H28E	1.1003	0.3177	0.6858	0.041*	0.556 (7)
H28F	1.0841	0.2116	0.7501	0.041*	0.556 (7)
O4	0.3394 (12)	0.6785 (6)	0.8119 (18)	0.0205 (19)	0.654 (7)
N4	0.2121 (3)	0.8208 (3)	0.8085 (2)	0.0229 (10)	0.654 (7)
C29	0.4147 (11)	0.8427 (10)	0.7597 (11)	0.028 (3)	0.654 (7)
H29A	0.4752	0.8870	0.8243	0.033*	0.654 (7)
H29B	0.3635	0.8896	0.7000	0.033*	0.654 (7)
H29C	0.4701	0.7967	0.7327	0.033*	0.654 (7)
C30	0.3170 (4)	0.7747 (3)	0.7932 (3)	0.0205 (10)	0.654 (7)
C31	0.1860 (9)	0.9350 (5)	0.7976 (8)	0.0283 (17)	0.654 (7)
H31A	0.2042	0.9679	0.8717	0.034*	0.654 (7)
H31B	0.0898	0.9430	0.7499	0.034*	0.654 (7)
H31C	0.2465	0.9706	0.7639	0.034*	0.654 (7)
C32	0.1180 (15)	0.7532 (12)	0.8495 (11)	0.030 (2)	0.654 (7)
H32A	0.1453	0.6787	0.8559	0.036*	0.654 (7)
H32B	0.0231	0.7554	0.7965	0.036*	0.654 (7)
H32C	0.1243	0.7814	0.9229	0.036*	0.654 (7)
O4'	0.312 (2)	0.6646 (12)	0.810 (3)	0.019 (3)	0.346 (7)
N4'	0.2828 (6)	0.8424 (5)	0.7762 (4)	0.0184 (18)	0.346 (7)
C29'	0.142 (3)	0.748 (2)	0.858 (2)	0.034 (5)	0.346 (7)
H29D	0.1246	0.6751	0.8791	0.041*	0.346 (7)
H29E	0.0585	0.7721	0.8007	0.041*	0.346 (7)
H29F	0.1708	0.7969	0.9235	0.041*	0.346 (7)
C30'	0.2524 (8)	0.7475 (5)	0.8120 (5)	0.022 (2)	0.346 (7)
C31'	0.2132 (17)	0.9405 (10)	0.7792 (16)	0.023 (3)	0.346 (7)
H31D	0.1200	0.9215	0.7765	0.028*	0.346 (7)
H31E	0.2084	0.9836	0.7147	0.028*	0.346 (7)
H31F	0.2647	0.9823	0.8484	0.028*	0.346 (7)
C32'	0.4106 (17)	0.854 (2)	0.746 (2)	0.019 (4)	0.346 (7)
H32D	0.4930	0.8586	0.8142	0.023*	0.346 (7)
H32E	0.4078	0.9197	0.7038	0.023*	0.346 (7)
H32F	0.4132	0.7915	0.6995	0.023*	0.346 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.04347 (14)	0.01313 (10)	0.01985 (11)	0.00236 (9)	−0.00130 (10)	0.00551 (8)
Br2	0.05477 (16)	0.01552 (11)	0.02162 (12)	0.00101 (10)	0.01403 (11)	0.00613 (8)
O1	0.0235 (7)	0.0134 (7)	0.0165 (7)	0.0034 (5)	0.0073 (6)	0.0003 (5)
O2	0.0257 (7)	0.0144 (7)	0.0169 (7)	0.0017 (6)	0.0075 (6)	−0.0002 (5)
N1	0.0254 (9)	0.0102 (8)	0.0142 (8)	0.0058 (7)	0.0059 (7)	0.0008 (6)
N2	0.0279 (10)	0.0105 (8)	0.0154 (9)	−0.0011 (7)	0.0050 (8)	−0.0003 (7)
C1	0.0167 (9)	0.0128 (9)	0.0113 (9)	0.0024 (7)	0.0023 (8)	0.0013 (7)
C2	0.0178 (10)	0.0165 (10)	0.0185 (10)	0.0055 (8)	0.0078 (8)	0.0022 (8)
C3	0.0172 (10)	0.0175 (10)	0.0186 (10)	0.0008 (8)	0.0089 (8)	0.0018 (8)
C4	0.0158 (9)	0.0129 (9)	0.0139 (9)	0.0018 (7)	0.0041 (8)	0.0015 (7)
C5	0.0186 (10)	0.0135 (9)	0.0181 (10)	0.0041 (8)	0.0051 (8)	0.0022 (7)
C6	0.0148 (10)	0.0201 (10)	0.0206 (10)	0.0043 (8)	0.0068 (8)	0.0000 (8)
C7	0.0174 (10)	0.0191 (10)	0.0193 (10)	0.0000 (8)	0.0096 (8)	0.0007 (8)
C8	0.0157 (10)	0.0144 (9)	0.0159 (10)	0.0011 (7)	0.0037 (8)	0.0028 (7)
C9	0.0160 (9)	0.0128 (9)	0.0096 (9)	0.0025 (7)	0.0037 (8)	−0.0009 (7)
C10	0.0143 (9)	0.0135 (9)	0.0116 (9)	0.0017 (7)	0.0031 (8)	0.0001 (7)
C11	0.0116 (9)	0.0142 (9)	0.0169 (10)	0.0024 (7)	0.0043 (8)	0.0023 (7)
C12	0.0159 (10)	0.0132 (9)	0.0174 (10)	0.0041 (7)	0.0062 (8)	0.0036 (7)
C13	0.0227 (10)	0.0130 (9)	0.0181 (10)	0.0024 (8)	0.0057 (8)	−0.0013 (7)
C14	0.0223 (10)	0.0179 (10)	0.0121 (9)	0.0009 (8)	0.0018 (8)	0.0012 (7)
C15	0.0200 (10)	0.0121 (9)	0.0192 (10)	0.0039 (8)	0.0051 (8)	0.0054 (8)
C16	0.0173 (10)	0.0117 (9)	0.0189 (10)	0.0002 (7)	0.0074 (8)	0.0010 (7)
C17	0.0161 (10)	0.0151 (9)	0.0130 (9)	0.0021 (7)	0.0058 (8)	0.0009 (7)
C18	0.0127 (9)	0.0145 (9)	0.0193 (10)	0.0031 (7)	0.0083 (8)	0.0038 (7)
C19	0.0191 (10)	0.0135 (9)	0.0164 (10)	0.0025 (8)	0.0065 (8)	0.0040 (7)
C20	0.0176 (10)	0.0169 (10)	0.0150 (10)	0.0015 (8)	0.0043 (8)	0.0013 (7)
C21	0.0213 (10)	0.0128 (9)	0.0197 (10)	−0.0001 (8)	0.0073 (9)	−0.0003 (7)
C22	0.0257 (11)	0.0135 (9)	0.0204 (10)	0.0026 (8)	0.0094 (9)	0.0061 (8)
C23	0.0352 (12)	0.0186 (10)	0.0154 (10)	0.0018 (9)	0.0074 (9)	0.0020 (8)
C24	0.0328 (12)	0.0121 (9)	0.0186 (10)	−0.0015 (8)	0.0062 (9)	−0.0011 (8)
O3	0.023 (5)	0.017 (3)	0.022 (3)	0.002 (2)	0.004 (3)	−0.001 (2)
N3	0.024 (3)	0.017 (3)	0.023 (2)	−0.006 (2)	0.006 (2)	0.0007 (18)
C25	0.027 (4)	0.026 (5)	0.025 (4)	−0.003 (4)	0.014 (3)	−0.007 (4)
C26	0.019 (3)	0.029 (4)	0.009 (2)	−0.001 (2)	0.000 (2)	−0.0051 (19)
C27	0.026 (5)	0.019 (4)	0.022 (4)	−0.004 (3)	0.004 (5)	0.000 (3)
C28	0.017 (5)	0.022 (4)	0.036 (6)	0.001 (3)	0.011 (4)	−0.011 (5)
O3'	0.028 (5)	0.014 (2)	0.022 (2)	0.001 (2)	0.004 (3)	−0.0015 (18)
N3'	0.028 (3)	0.024 (2)	0.0216 (18)	−0.0096 (17)	0.0109 (17)	−0.0037 (14)
C25'	0.036 (5)	0.040 (6)	0.047 (7)	−0.002 (4)	0.018 (4)	0.001 (4)
C26'	0.019 (3)	0.022 (3)	0.0159 (19)	−0.0001 (18)	0.0043 (17)	−0.0034 (17)
C27'	0.044 (6)	0.027 (3)	0.029 (4)	−0.013 (3)	0.007 (5)	0.009 (3)
C28'	0.022 (3)	0.050 (6)	0.028 (4)	−0.005 (4)	0.007 (3)	−0.008 (4)
O4	0.023 (4)	0.015 (2)	0.018 (2)	0.002 (2)	0.001 (4)	−0.003 (2)
N4	0.0200 (17)	0.0206 (19)	0.0267 (16)	0.0044 (13)	0.0065 (13)	−0.0019 (12)
C29	0.036 (4)	0.029 (4)	0.017 (3)	0.000 (3)	0.009 (3)	−0.004 (3)
C30	0.022 (2)	0.022 (3)	0.0114 (16)	0.0008 (18)	−0.0018 (15)	−0.0035 (14)
C31	0.021 (3)	0.020 (2)	0.040 (4)	0.006 (2)	0.007 (3)	−0.005 (2)
C32	0.021 (4)	0.047 (4)	0.024 (3)	0.000 (3)	0.011 (3)	0.006 (3)
O4'	0.018 (7)	0.014 (4)	0.020 (4)	0.003 (5)	0.001 (6)	−0.008 (5)
N4'	0.020 (3)	0.015 (3)	0.018 (3)	0.005 (2)	0.004 (2)	−0.003 (2)
C29'	0.018 (8)	0.040 (9)	0.041 (9)	−0.013 (6)	0.010 (6)	−0.019 (7)
C30'	0.021 (4)	0.025 (5)	0.012 (3)	−0.004 (4)	−0.002 (3)	−0.001 (3)
C31'	0.018 (6)	0.020 (4)	0.032 (5)	0.008 (4)	0.008 (4)	0.002 (3)
C32'	0.008 (5)	0.027 (6)	0.022 (7)	−0.005 (4)	0.005 (4)	0.006 (4)

Geometric parameters (Å, º) top

Br1—C15	1.9013 (18)	C25—C26	1.487 (16)
Br2—C22	1.9014 (18)	C25—H25A	0.98
O1—C11	1.231 (2)	C25—H25B	0.98
O2—C18	1.227 (2)	C25—H25C	0.98
N1—C11	1.357 (2)	C27—H27A	0.98
N1—C12	1.417 (2)	C27—H27B	0.98
N1—H1N	0.84 (2)	C27—H27C	0.98
N2—C18	1.353 (2)	C28—H28A	0.98
N2—C19	1.414 (2)	C28—H28B	0.98
N2—H2N	0.81 (2)	C28—H28C	0.98
C1—C2	1.372 (2)	O3'—C26'	1.229 (8)
C1—C9	1.431 (2)	N3'—C26'	1.330 (6)
C1—C11	1.502 (2)	N3'—C28'	1.457 (13)
C2—C3	1.401 (2)	N3'—C27'	1.458 (8)
C2—H2	0.95	C25'—C26'	1.488 (14)
C3—C4	1.374 (3)	C25'—H25D	0.98
C3—H3	0.95	C25'—H25E	0.98
C4—C10	1.422 (3)	C25'—H25F	0.98
C4—C18	1.507 (2)	C27'—H27D	0.98
C5—C6	1.363 (3)	C27'—H27E	0.98
C5—C10	1.422 (2)	C27'—H27F	0.98
C5—H5	0.95	C28'—H28D	0.98
C6—C7	1.406 (3)	C28'—H28E	0.98
C6—H6	0.95	C28'—H28F	0.98
C7—C8	1.369 (3)	O4—C30	1.242 (8)
C7—H7	0.95	N4—C30	1.337 (5)
C8—C9	1.423 (3)	N4—C31	1.460 (7)
C8—H8	0.95	N4—C32	1.503 (11)
C9—C10	1.423 (2)	C29—C30	1.479 (11)
C12—C13	1.393 (3)	C29—H29A	0.98
C12—C17	1.398 (3)	C29—H29B	0.98
C13—C14	1.391 (2)	C29—H29C	0.98
C13—H13	0.95	C30—O4	1.242 (8)
C14—C15	1.386 (3)	C31—H31A	0.98
C14—H14	0.95	C31—H31B	0.98
C15—C16	1.384 (3)	C31—H31C	0.98
C16—C17	1.386 (2)	C32—H32A	0.98
C16—H16	0.95	C32—H32B	0.98
C17—H17	0.95	C32—H32C	0.98
C19—C24	1.397 (3)	O4'—C30'	1.236 (13)
C19—C20	1.397 (3)	N4'—C30'	1.338 (9)
C20—C21	1.390 (2)	N4'—C31'	1.461 (11)
C20—H20	0.95	N4'—C32'	1.525 (16)
C21—C22	1.384 (3)	C29'—C30'	1.468 (18)
C21—H21	0.95	C29'—H29D	0.98
C22—C23	1.386 (3)	C29'—H29E	0.98
C23—C24	1.385 (3)	C29'—H29F	0.98
C23—H23	0.95	C31'—H31D	0.98
C24—H24	0.95	C31'—H31E	0.98
O3—C26	1.231 (10)	C31'—H31F	0.98
N3—C26	1.328 (8)	C32'—H32D	0.98
N3—C28	1.455 (16)	C32'—H32E	0.98
N3—C27	1.476 (10)	C32'—H32F	0.98

C11—N1—C12	127.23 (16)	C21—C22—Br2	119.34 (15)
C11—N1—H1N	116.2 (16)	C23—C22—Br2	118.80 (15)
C12—N1—H1N	116.3 (16)	C24—C23—C22	118.63 (19)
C18—N2—C19	129.45 (17)	C24—C23—H23	120.7
C18—N2—H2N	117.0 (15)	C22—C23—H23	120.7
C19—N2—H2N	113.5 (15)	C23—C24—C19	120.67 (18)
C2—C1—C9	119.96 (16)	C23—C24—H24	119.7
C2—C1—C11	116.99 (15)	C19—C24—H24	119.7
C9—C1—C11	123.05 (15)	C26—N3—C28	120.6 (9)
C1—C2—C3	121.09 (16)	C26—N3—C27	124.9 (8)
C1—C2—H2	119.5	C28—N3—C27	113.7 (10)
C3—C2—H2	119.5	O3—C26—N3	123.8 (9)
C4—C3—C2	120.59 (17)	O3—C26—C25	114.8 (9)
C4—C3—H3	119.7	N3—C26—C25	121.3 (7)
C2—C3—H3	119.7	C26'—N3'—C28'	122.0 (6)
C3—C4—C10	120.19 (16)	C26'—N3'—C27'	124.8 (7)
C3—C4—C18	118.68 (16)	C28'—N3'—C27'	113.1 (7)
C10—C4—C18	121.09 (15)	C26'—C25'—H25D	109.6
C6—C5—C10	120.79 (16)	C26'—C25'—H25E	109.5
C6—C5—H5	119.6	H25D—C25'—H25E	109.5
C10—C5—H5	119.6	C26'—C25'—H25F	109.3
C5—C6—C7	120.67 (16)	H25D—C25'—H25F	109.5
C5—C6—H6	119.7	H25E—C25'—H25F	109.5
C7—C6—H6	119.7	O3'—C26'—N3'	123.7 (7)
C8—C7—C6	120.29 (17)	O3'—C26'—C25'	116.7 (9)
C8—C7—H7	119.9	N3'—C26'—C25'	119.5 (8)
C6—C7—H7	119.9	N3'—C27'—H27D	109.5
C7—C8—C9	120.74 (16)	N3'—C27'—H27E	109.5
C7—C8—H8	119.6	H27D—C27'—H27E	109.5
C9—C8—H8	119.6	N3'—C27'—H27F	109.5
C8—C9—C10	118.71 (15)	H27D—C27'—H27F	109.5
C8—C9—C1	122.53 (16)	H27E—C27'—H27F	109.5
C10—C9—C1	118.74 (15)	N3'—C28'—H28D	109.5
C4—C10—C5	121.84 (16)	N3'—C28'—H28E	109.5
C4—C10—C9	119.35 (15)	H28D—C28'—H28E	109.5
C5—C10—C9	118.80 (15)	N3'—C28'—H28F	109.4
O1—C11—N1	125.01 (17)	H28D—C28'—H28F	109.5
O1—C11—C1	120.76 (16)	H28E—C28'—H28F	109.5
N1—C11—C1	114.18 (16)	C30—N4—C31	125.5 (5)
C13—C12—C17	119.83 (16)	C30—N4—C32	118.6 (7)
C13—C12—N1	116.77 (17)	C31—N4—C32	115.7 (7)
C17—C12—N1	123.41 (17)	O4—C30—N4	122.4 (8)
C14—C13—C12	120.73 (18)	O4—C30—N4	122.4 (8)
C14—C13—H13	119.6	O4—C30—C29	118.9 (9)
C12—C13—H13	119.6	O4—C30—C29	118.9 (9)
C15—C14—C13	118.27 (18)	N4—C30—C29	118.6 (6)
C15—C14—H14	120.9	C30'—N4'—C31'	124.2 (8)
C13—C14—H14	120.9	C30'—N4'—C32'	118.4 (11)
C16—C15—C14	122.03 (17)	C31'—N4'—C32'	116.8 (11)
C16—C15—Br1	118.91 (14)	C30'—C29'—H29D	109.5
C14—C15—Br1	119.05 (15)	C30'—C29'—H29E	109.4
C15—C16—C17	119.36 (17)	H29D—C29'—H29E	109.5
C15—C16—H16	120.3	C30'—C29'—H29F	109.5
C17—C16—H16	120.3	H29D—C29'—H29F	109.5
C16—C17—C12	119.76 (17)	H29E—C29'—H29F	109.5
C16—C17—H17	120.1	O4'—C30'—N4'	124.1 (16)
C12—C17—H17	120.1	O4'—C30'—C29'	120.9 (18)
O2—C18—N2	125.32 (17)	N4'—C30'—C29'	115.0 (12)
O2—C18—C4	121.85 (17)	N4'—C31'—H31D	109.5
N2—C18—C4	112.82 (16)	N4'—C31'—H31E	109.5
C24—C19—C20	119.70 (17)	H31D—C31'—H31E	109.5
C24—C19—N2	116.18 (17)	N4'—C31'—H31F	109.5
C20—C19—N2	124.11 (17)	H31D—C31'—H31F	109.5
C21—C20—C19	119.86 (18)	H31E—C31'—H31F	109.5
C21—C20—H20	120.1	N4'—C32'—H32D	109.5
C19—C20—H20	120.1	N4'—C32'—H32E	109.5
C22—C21—C20	119.26 (18)	H32D—C32'—H32E	109.5
C22—C21—H21	120.4	N4'—C32'—H32F	109.5
C20—C21—H21	120.4	H32D—C32'—H32F	109.5
C21—C22—C23	121.86 (17)	H32E—C32'—H32F	109.5

C9—C1—C2—C3	2.3 (3)	C13—C12—C17—C16	−0.9 (3)
C11—C1—C2—C3	−177.90 (18)	N1—C12—C17—C16	179.49 (16)
C1—C2—C3—C4	0.1 (3)	C19—N2—C18—O2	4.7 (3)
C2—C3—C4—C10	−2.3 (3)	C19—N2—C18—C4	−174.05 (17)
C2—C3—C4—C18	175.41 (18)	C3—C4—C18—O2	−102.4 (2)
C10—C5—C6—C7	0.0 (3)	C10—C4—C18—O2	75.2 (2)
C5—C6—C7—C8	−0.2 (3)	C3—C4—C18—N2	76.3 (2)
C6—C7—C8—C9	0.5 (3)	C10—C4—C18—N2	−106.0 (2)
C7—C8—C9—C10	−0.6 (3)	C18—N2—C19—C24	−179.70 (19)
C7—C8—C9—C1	−179.19 (18)	C18—N2—C19—C20	1.6 (3)
C2—C1—C9—C8	176.20 (17)	C24—C19—C20—C21	−0.8 (3)
C11—C1—C9—C8	−3.6 (3)	N2—C19—C20—C21	177.91 (17)
C2—C1—C9—C10	−2.4 (3)	C19—C20—C21—C22	−0.3 (3)
C11—C1—C9—C10	177.81 (17)	C20—C21—C22—C23	1.5 (3)
C3—C4—C10—C5	−176.67 (18)	C20—C21—C22—Br2	−179.05 (13)
C18—C4—C10—C5	5.7 (3)	C21—C22—C23—C24	−1.5 (3)
C3—C4—C10—C9	2.1 (3)	Br2—C22—C23—C24	179.00 (15)
C18—C4—C10—C9	−175.54 (17)	C22—C23—C24—C19	0.4 (3)
C6—C5—C10—C4	178.69 (18)	C20—C19—C24—C23	0.7 (3)
C6—C5—C10—C9	−0.1 (3)	N2—C19—C24—C23	−178.07 (18)
C8—C9—C10—C4	−178.42 (17)	C28—N3—C26—O3	4.5 (17)
C1—C9—C10—C4	0.2 (3)	C27—N3—C26—O3	174.0 (15)
C8—C9—C10—C5	0.4 (3)	C28—N3—C26—C25	−175.8 (13)
C1—C9—C10—C5	179.02 (17)	C27—N3—C26—C25	−6.4 (13)
C12—N1—C11—O1	3.9 (3)	C28'—N3'—C26'—O3'	1.5 (13)
C12—N1—C11—C1	−173.45 (16)	C27'—N3'—C26'—O3'	−175.2 (12)
C2—C1—C11—O1	−61.0 (2)	C28'—N3'—C26'—C25'	−179.0 (12)
C9—C1—C11—O1	118.8 (2)	C27'—N3'—C26'—C25'	4.3 (12)
C2—C1—C11—N1	116.43 (19)	O4—O4—C30—N4	0 (3)
C9—C1—C11—N1	−63.8 (2)	O4—O4—C30—C29	0 (4)
C11—N1—C12—C13	162.24 (18)	C31—N4—C30—O4	174.5 (12)
C11—N1—C12—C17	−18.1 (3)	C32—N4—C30—O4	−0.1 (13)
C17—C12—C13—C14	1.1 (3)	C31—N4—C30—O4	174.5 (12)
N1—C12—C13—C14	−179.22 (16)	C32—N4—C30—O4	−0.1 (13)
C12—C13—C14—C15	−0.2 (3)	C31—N4—C30—C29	−1.6 (9)
C13—C14—C15—C16	−1.0 (3)	C32—N4—C30—C29	−176.2 (9)
C13—C14—C15—Br1	177.59 (14)	C31'—N4'—C30'—O4'	−180 (2)
C14—C15—C16—C17	1.3 (3)	C32'—N4'—C30'—O4'	−9 (2)
Br1—C15—C16—C17	−177.35 (13)	C31'—N4'—C30'—C29'	−0.9 (17)
C15—C16—C17—C12	−0.3 (3)	C32'—N4'—C30'—C29'	170.0 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4	0.84 (2)	2.03 (3)	2.865 (13)	170 (2)
N2—H2N···O3′ⁱ	0.81 (2)	2.00 (3)	2.797 (13)	171 (2)
C2—H2···O1ⁱ	0.95	2.50	3.423 (2)	163
C6—H6···O2ⁱⁱ	0.95	2.49	3.426 (2)	169
C14—H14···O4ⁱⁱⁱ	0.95	2.55	3.48 (2)	167

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

Experimental details

Crystal data
Chemical formula	C₂₄H₁₆Br₂N₂O₂·2C₄H₉NO
M_r	698.45
Crystal system, space group	Triclinic, P1
Temperature (K)	93
a, b, c (Å)	10.4589 (9), 12.4485 (5), 12.8439 (11)
α, β, γ (°)	90.775 (2), 111.370 (4), 92.944 (2)
V (Å³)	1554.3 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.65
Crystal size (mm)	0.47 × 0.33 × 0.17

Data collection
Diffractometer	Rigaku AFC10/Saturn724+ diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.364, 0.637
No. of measured, independent and observed [I > 2σ(I)] reflections	12655, 6836, 5420
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.065, 0.95
No. of reflections	6836
No. of parameters	509
No. of restraints	64
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.73

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4	0.84 (2)	2.03 (3)	2.865 (13)	170 (2)
N2—H2N···O3'ⁱ	0.81 (2)	2.00 (3)	2.797 (13)	171 (2)
C2—H2···O1ⁱ	0.95	2.50	3.423 (2)	163
C6—H6···O2ⁱⁱ	0.95	2.49	3.426 (2)	169
C14—H14···O4ⁱⁱⁱ	0.95	2.55	3.48 (2)	167

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

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 06298919. Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Jing, L.-H. (2008). Acta Cryst. E64, o2379. Web of Science CSD CrossRef IUCr Journals 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 06298918. Google Scholar

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o27

doi:10.1107/S1600536809051447

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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