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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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[Fukuzumi, T., Tajiri, T., Tsukada, H. & Yoshida, J. (1994). Jpn Patent JP 06298919.]); Tsukada et al. (1994[Tsukada, H., Tajiri, T., Fukuzumi, T. & Yoshida, J. (1994). Jpn Patent JP 06298918.]). For the crystal structure of the 4-methyl­phenyl analog, see: Jing (2008[Jing, L.-H. (2008). Acta Cryst. E64, o2379.]).

[Scheme 1]

Experimental

Crystal data
  • C24H16Br2N2O2·2C4H9NO

  • Mr = 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[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.364, Tmax = 0.637

  • 12655 measured reflections

  • 6836 independent reflections

  • 5420 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.73 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Rigaku (2004). RAPID-AUTO. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


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 CO 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.

Refinement top

Both dimethylacetamide molecules are disordered over two positions. The site-occupation factors for the disordered atoms were refined to 0.444 (7) and 0.556 (7), respectively, for the minor and major components of one of the dimethylacetamide molecules (with O3), and to 0.654 (7) and 0.346 (7), respectively, for the major and minor components of the other molecule. The corresponding distances in the major and minor disorder components were restrained to be the same. The Uij components of atoms O3, O3', C26, C27', C28', C31' and C32'were restrained to an approximate isotropic behaviour. N-bound H atoms were located in a difference Fourier map and refined isotropically (N–H = 0.84 (2) and 0.81 (2) Å). The C-bound H atoms were placed in calculated positions, with C–H = 0.95 or 0.98 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(C).

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
[Figure 1] 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
C24H16Br2N2O2·2C4H9NOZ = 2
Mr = 698.45F(000) = 712
Triclinic, P1Dx = 1.492 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.4589 (9) ÅCell parameters from 4940 reflections
b = 12.4485 (5) Åθ = 3.2–27.5°
c = 12.8439 (11) ŵ = 2.65 mm1
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 Anode5420 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 28.5714 pixels mm-1θmax = 27.5°, θmin = 3.2°
ω scansh = 1113
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1516
Tmin = 0.364, Tmax = 0.637l = 1614
12655 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065H atoms treated by a mixture of independent and constrained refinement
S = 0.95 w = 1/[σ2(Fo2) + (0.0312P)2]
where P = (Fo2 + 2Fc2)/3
6836 reflections(Δ/σ)max = 0.001
509 parametersΔρmax = 0.35 e Å3
64 restraintsΔρmin = 0.73 e Å3
Crystal data top
C24H16Br2N2O2·2C4H9NOγ = 92.944 (2)°
Mr = 698.45V = 1554.3 (2) Å3
Triclinic, P1Z = 2
a = 10.4589 (9) ÅMo Kα radiation
b = 12.4485 (5) ŵ = 2.65 mm1
c = 12.8439 (11) ÅT = 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)
Tmin = 0.364, Tmax = 0.637Rint = 0.024
12655 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.02964 restraints
wR(F2) = 0.065H atoms treated by a mixture of independent and constrained refinement
S = 0.95Δρmax = 0.35 e Å3
6836 reflectionsΔρmin = 0.73 e Å3
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
xyzUiso*/UeqOcc. (<1)
Br10.53236 (2)0.112534 (16)0.932514 (17)0.02903 (7)
Br20.22415 (2)1.394801 (16)0.057404 (18)0.03060 (7)
O10.32331 (13)0.45436 (10)0.48313 (11)0.0177 (3)
O20.31551 (13)1.04379 (10)0.50572 (11)0.0191 (3)
N10.34837 (17)0.50996 (13)0.66106 (14)0.0168 (3)
H1N0.348 (2)0.5650 (19)0.700 (2)0.039 (7)*
N20.23601 (17)0.99105 (13)0.32026 (14)0.0189 (4)
H2N0.203 (2)0.9395 (17)0.2781 (19)0.024 (6)*
C10.30036 (18)0.63948 (14)0.51685 (15)0.0143 (4)
C20.39398 (19)0.68975 (15)0.47878 (16)0.0171 (4)
H20.46700.65080.47290.021*
C30.38368 (19)0.79752 (15)0.44845 (16)0.0172 (4)
H30.44950.83070.42220.021*
C40.27922 (18)0.85564 (14)0.45630 (15)0.0145 (4)
C50.06363 (19)0.86155 (15)0.49518 (16)0.0170 (4)
H50.05590.93480.47500.020*
C60.03434 (19)0.81135 (15)0.52719 (16)0.0183 (4)
H60.10950.84990.52910.022*
C70.02522 (19)0.70304 (15)0.55738 (16)0.0178 (4)
H70.09400.66900.57980.021*
C80.08240 (18)0.64638 (15)0.55463 (16)0.0159 (4)
H80.08720.57310.57460.019*
C90.18715 (18)0.69610 (14)0.52222 (15)0.0130 (4)
C100.17723 (18)0.80569 (14)0.49159 (15)0.0136 (4)
C110.32325 (18)0.52500 (14)0.55106 (16)0.0144 (4)
C120.38661 (19)0.41416 (14)0.71995 (16)0.0153 (4)
C130.44442 (19)0.42461 (15)0.83616 (16)0.0184 (4)
H130.45520.49370.87170.022*
C140.48654 (19)0.33506 (15)0.90073 (16)0.0187 (4)
H140.52620.34200.98000.022*
C150.46910 (19)0.23536 (15)0.84642 (16)0.0175 (4)
C160.40962 (18)0.22272 (14)0.73121 (16)0.0158 (4)
H160.39720.15320.69620.019*
C170.36833 (18)0.31242 (14)0.66737 (16)0.0145 (4)
H170.32780.30480.58820.017*
C180.27844 (18)0.97352 (14)0.43114 (16)0.0147 (4)
C190.23255 (19)1.08886 (15)0.26482 (16)0.0162 (4)
C200.27827 (18)1.18916 (15)0.31961 (16)0.0169 (4)
H200.31171.19490.39900.020*
C210.27480 (19)1.28043 (15)0.25775 (16)0.0180 (4)
H210.30531.34900.29440.022*
C220.2264 (2)1.27038 (15)0.14216 (17)0.0195 (4)
C230.1782 (2)1.17201 (15)0.08598 (17)0.0236 (5)
H230.14331.16690.00660.028*
C240.1820 (2)1.08126 (15)0.14807 (17)0.0222 (4)
H240.15001.01320.11080.027*
O30.9394 (16)0.1698 (9)0.8232 (17)0.021 (2)0.444 (7)
N30.8990 (5)0.3438 (4)0.7831 (4)0.0226 (14)0.444 (7)
C251.0986 (17)0.2599 (10)0.7668 (15)0.025 (2)0.444 (7)
H25A1.16490.31540.81420.030*0.444 (7)
H25B1.07620.27640.68790.030*0.444 (7)
H25C1.13870.18960.78100.030*0.444 (7)
C260.9712 (6)0.2573 (4)0.7930 (4)0.0205 (15)0.444 (7)
C270.9413 (14)0.4520 (8)0.7573 (15)0.024 (2)0.444 (7)
H27A0.98820.49420.82710.029*0.444 (7)
H27B0.85990.48810.71080.029*0.444 (7)
H27C1.00410.44540.71680.029*0.444 (7)
C280.7799 (19)0.3420 (14)0.8162 (18)0.024 (3)0.444 (7)
H28A0.72460.27430.78930.029*0.444 (7)
H28B0.72420.40260.78370.029*0.444 (7)
H28C0.81070.34780.89800.029*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)
H25D0.72520.26930.85000.048*0.556 (7)
H25E0.72720.36120.76460.048*0.556 (7)
H25F0.81980.37780.89460.048*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)
H27D0.92530.46730.68940.043*0.556 (7)
H27E1.07400.48320.78640.043*0.556 (7)
H27F0.93870.48210.81690.043*0.556 (7)
C28'1.0974 (13)0.2903 (8)0.7562 (12)0.034 (3)0.556 (7)
H28D1.18420.31130.81740.041*0.556 (7)
H28E1.10030.31770.68580.041*0.556 (7)
H28F1.08410.21160.75010.041*0.556 (7)
O40.3394 (12)0.6785 (6)0.8119 (18)0.0205 (19)0.654 (7)
N40.2121 (3)0.8208 (3)0.8085 (2)0.0229 (10)0.654 (7)
C290.4147 (11)0.8427 (10)0.7597 (11)0.028 (3)0.654 (7)
H29A0.47520.88700.82430.033*0.654 (7)
H29B0.36350.88960.70000.033*0.654 (7)
H29C0.47010.79670.73270.033*0.654 (7)
C300.3170 (4)0.7747 (3)0.7932 (3)0.0205 (10)0.654 (7)
C310.1860 (9)0.9350 (5)0.7976 (8)0.0283 (17)0.654 (7)
H31A0.20420.96790.87170.034*0.654 (7)
H31B0.08980.94300.74990.034*0.654 (7)
H31C0.24650.97060.76390.034*0.654 (7)
C320.1180 (15)0.7532 (12)0.8495 (11)0.030 (2)0.654 (7)
H32A0.14530.67870.85590.036*0.654 (7)
H32B0.02310.75540.79650.036*0.654 (7)
H32C0.12430.78140.92290.036*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)
H29D0.12460.67510.87910.041*0.346 (7)
H29E0.05850.77210.80070.041*0.346 (7)
H29F0.17080.79690.92350.041*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)
H31D0.12000.92150.77650.028*0.346 (7)
H31E0.20840.98360.71470.028*0.346 (7)
H31F0.26470.98230.84840.028*0.346 (7)
C32'0.4106 (17)0.854 (2)0.746 (2)0.019 (4)0.346 (7)
H32D0.49300.85860.81420.023*0.346 (7)
H32E0.40780.91970.70380.023*0.346 (7)
H32F0.41320.79150.69950.023*0.346 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.04347 (14)0.01313 (10)0.01985 (11)0.00236 (9)0.00130 (10)0.00551 (8)
Br20.05477 (16)0.01552 (11)0.02162 (12)0.00101 (10)0.01403 (11)0.00613 (8)
O10.0235 (7)0.0134 (7)0.0165 (7)0.0034 (5)0.0073 (6)0.0003 (5)
O20.0257 (7)0.0144 (7)0.0169 (7)0.0017 (6)0.0075 (6)0.0002 (5)
N10.0254 (9)0.0102 (8)0.0142 (8)0.0058 (7)0.0059 (7)0.0008 (6)
N20.0279 (10)0.0105 (8)0.0154 (9)0.0011 (7)0.0050 (8)0.0003 (7)
C10.0167 (9)0.0128 (9)0.0113 (9)0.0024 (7)0.0023 (8)0.0013 (7)
C20.0178 (10)0.0165 (10)0.0185 (10)0.0055 (8)0.0078 (8)0.0022 (8)
C30.0172 (10)0.0175 (10)0.0186 (10)0.0008 (8)0.0089 (8)0.0018 (8)
C40.0158 (9)0.0129 (9)0.0139 (9)0.0018 (7)0.0041 (8)0.0015 (7)
C50.0186 (10)0.0135 (9)0.0181 (10)0.0041 (8)0.0051 (8)0.0022 (7)
C60.0148 (10)0.0201 (10)0.0206 (10)0.0043 (8)0.0068 (8)0.0000 (8)
C70.0174 (10)0.0191 (10)0.0193 (10)0.0000 (8)0.0096 (8)0.0007 (8)
C80.0157 (10)0.0144 (9)0.0159 (10)0.0011 (7)0.0037 (8)0.0028 (7)
C90.0160 (9)0.0128 (9)0.0096 (9)0.0025 (7)0.0037 (8)0.0009 (7)
C100.0143 (9)0.0135 (9)0.0116 (9)0.0017 (7)0.0031 (8)0.0001 (7)
C110.0116 (9)0.0142 (9)0.0169 (10)0.0024 (7)0.0043 (8)0.0023 (7)
C120.0159 (10)0.0132 (9)0.0174 (10)0.0041 (7)0.0062 (8)0.0036 (7)
C130.0227 (10)0.0130 (9)0.0181 (10)0.0024 (8)0.0057 (8)0.0013 (7)
C140.0223 (10)0.0179 (10)0.0121 (9)0.0009 (8)0.0018 (8)0.0012 (7)
C150.0200 (10)0.0121 (9)0.0192 (10)0.0039 (8)0.0051 (8)0.0054 (8)
C160.0173 (10)0.0117 (9)0.0189 (10)0.0002 (7)0.0074 (8)0.0010 (7)
C170.0161 (10)0.0151 (9)0.0130 (9)0.0021 (7)0.0058 (8)0.0009 (7)
C180.0127 (9)0.0145 (9)0.0193 (10)0.0031 (7)0.0083 (8)0.0038 (7)
C190.0191 (10)0.0135 (9)0.0164 (10)0.0025 (8)0.0065 (8)0.0040 (7)
C200.0176 (10)0.0169 (10)0.0150 (10)0.0015 (8)0.0043 (8)0.0013 (7)
C210.0213 (10)0.0128 (9)0.0197 (10)0.0001 (8)0.0073 (9)0.0003 (7)
C220.0257 (11)0.0135 (9)0.0204 (10)0.0026 (8)0.0094 (9)0.0061 (8)
C230.0352 (12)0.0186 (10)0.0154 (10)0.0018 (9)0.0074 (9)0.0020 (8)
C240.0328 (12)0.0121 (9)0.0186 (10)0.0015 (8)0.0062 (9)0.0011 (8)
O30.023 (5)0.017 (3)0.022 (3)0.002 (2)0.004 (3)0.001 (2)
N30.024 (3)0.017 (3)0.023 (2)0.006 (2)0.006 (2)0.0007 (18)
C250.027 (4)0.026 (5)0.025 (4)0.003 (4)0.014 (3)0.007 (4)
C260.019 (3)0.029 (4)0.009 (2)0.001 (2)0.000 (2)0.0051 (19)
C270.026 (5)0.019 (4)0.022 (4)0.004 (3)0.004 (5)0.000 (3)
C280.017 (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)
O40.023 (4)0.015 (2)0.018 (2)0.002 (2)0.001 (4)0.003 (2)
N40.0200 (17)0.0206 (19)0.0267 (16)0.0044 (13)0.0065 (13)0.0019 (12)
C290.036 (4)0.029 (4)0.017 (3)0.000 (3)0.009 (3)0.004 (3)
C300.022 (2)0.022 (3)0.0114 (16)0.0008 (18)0.0018 (15)0.0035 (14)
C310.021 (3)0.020 (2)0.040 (4)0.006 (2)0.007 (3)0.005 (2)
C320.021 (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—C151.9013 (18)C25—C261.487 (16)
Br2—C221.9014 (18)C25—H25A0.98
O1—C111.231 (2)C25—H25B0.98
O2—C181.227 (2)C25—H25C0.98
N1—C111.357 (2)C27—H27A0.98
N1—C121.417 (2)C27—H27B0.98
N1—H1N0.84 (2)C27—H27C0.98
N2—C181.353 (2)C28—H28A0.98
N2—C191.414 (2)C28—H28B0.98
N2—H2N0.81 (2)C28—H28C0.98
C1—C21.372 (2)O3'—C26'1.229 (8)
C1—C91.431 (2)N3'—C26'1.330 (6)
C1—C111.502 (2)N3'—C28'1.457 (13)
C2—C31.401 (2)N3'—C27'1.458 (8)
C2—H20.95C25'—C26'1.488 (14)
C3—C41.374 (3)C25'—H25D0.98
C3—H30.95C25'—H25E0.98
C4—C101.422 (3)C25'—H25F0.98
C4—C181.507 (2)C27'—H27D0.98
C5—C61.363 (3)C27'—H27E0.98
C5—C101.422 (2)C27'—H27F0.98
C5—H50.95C28'—H28D0.98
C6—C71.406 (3)C28'—H28E0.98
C6—H60.95C28'—H28F0.98
C7—C81.369 (3)O4—C301.242 (8)
C7—H70.95N4—C301.337 (5)
C8—C91.423 (3)N4—C311.460 (7)
C8—H80.95N4—C321.503 (11)
C9—C101.423 (2)C29—C301.479 (11)
C12—C131.393 (3)C29—H29A0.98
C12—C171.398 (3)C29—H29B0.98
C13—C141.391 (2)C29—H29C0.98
C13—H130.95C30—O41.242 (8)
C14—C151.386 (3)C31—H31A0.98
C14—H140.95C31—H31B0.98
C15—C161.384 (3)C31—H31C0.98
C16—C171.386 (2)C32—H32A0.98
C16—H160.95C32—H32B0.98
C17—H170.95C32—H32C0.98
C19—C241.397 (3)O4'—C30'1.236 (13)
C19—C201.397 (3)N4'—C30'1.338 (9)
C20—C211.390 (2)N4'—C31'1.461 (11)
C20—H200.95N4'—C32'1.525 (16)
C21—C221.384 (3)C29'—C30'1.468 (18)
C21—H210.95C29'—H29D0.98
C22—C231.386 (3)C29'—H29E0.98
C23—C241.385 (3)C29'—H29F0.98
C23—H230.95C31'—H31D0.98
C24—H240.95C31'—H31E0.98
O3—C261.231 (10)C31'—H31F0.98
N3—C261.328 (8)C32'—H32D0.98
N3—C281.455 (16)C32'—H32E0.98
N3—C271.476 (10)C32'—H32F0.98
C11—N1—C12127.23 (16)C21—C22—Br2119.34 (15)
C11—N1—H1N116.2 (16)C23—C22—Br2118.80 (15)
C12—N1—H1N116.3 (16)C24—C23—C22118.63 (19)
C18—N2—C19129.45 (17)C24—C23—H23120.7
C18—N2—H2N117.0 (15)C22—C23—H23120.7
C19—N2—H2N113.5 (15)C23—C24—C19120.67 (18)
C2—C1—C9119.96 (16)C23—C24—H24119.7
C2—C1—C11116.99 (15)C19—C24—H24119.7
C9—C1—C11123.05 (15)C26—N3—C28120.6 (9)
C1—C2—C3121.09 (16)C26—N3—C27124.9 (8)
C1—C2—H2119.5C28—N3—C27113.7 (10)
C3—C2—H2119.5O3—C26—N3123.8 (9)
C4—C3—C2120.59 (17)O3—C26—C25114.8 (9)
C4—C3—H3119.7N3—C26—C25121.3 (7)
C2—C3—H3119.7C26'—N3'—C28'122.0 (6)
C3—C4—C10120.19 (16)C26'—N3'—C27'124.8 (7)
C3—C4—C18118.68 (16)C28'—N3'—C27'113.1 (7)
C10—C4—C18121.09 (15)C26'—C25'—H25D109.6
C6—C5—C10120.79 (16)C26'—C25'—H25E109.5
C6—C5—H5119.6H25D—C25'—H25E109.5
C10—C5—H5119.6C26'—C25'—H25F109.3
C5—C6—C7120.67 (16)H25D—C25'—H25F109.5
C5—C6—H6119.7H25E—C25'—H25F109.5
C7—C6—H6119.7O3'—C26'—N3'123.7 (7)
C8—C7—C6120.29 (17)O3'—C26'—C25'116.7 (9)
C8—C7—H7119.9N3'—C26'—C25'119.5 (8)
C6—C7—H7119.9N3'—C27'—H27D109.5
C7—C8—C9120.74 (16)N3'—C27'—H27E109.5
C7—C8—H8119.6H27D—C27'—H27E109.5
C9—C8—H8119.6N3'—C27'—H27F109.5
C8—C9—C10118.71 (15)H27D—C27'—H27F109.5
C8—C9—C1122.53 (16)H27E—C27'—H27F109.5
C10—C9—C1118.74 (15)N3'—C28'—H28D109.5
C4—C10—C5121.84 (16)N3'—C28'—H28E109.5
C4—C10—C9119.35 (15)H28D—C28'—H28E109.5
C5—C10—C9118.80 (15)N3'—C28'—H28F109.4
O1—C11—N1125.01 (17)H28D—C28'—H28F109.5
O1—C11—C1120.76 (16)H28E—C28'—H28F109.5
N1—C11—C1114.18 (16)C30—N4—C31125.5 (5)
C13—C12—C17119.83 (16)C30—N4—C32118.6 (7)
C13—C12—N1116.77 (17)C31—N4—C32115.7 (7)
C17—C12—N1123.41 (17)O4—C30—N4122.4 (8)
C14—C13—C12120.73 (18)O4—C30—N4122.4 (8)
C14—C13—H13119.6O4—C30—C29118.9 (9)
C12—C13—H13119.6O4—C30—C29118.9 (9)
C15—C14—C13118.27 (18)N4—C30—C29118.6 (6)
C15—C14—H14120.9C30'—N4'—C31'124.2 (8)
C13—C14—H14120.9C30'—N4'—C32'118.4 (11)
C16—C15—C14122.03 (17)C31'—N4'—C32'116.8 (11)
C16—C15—Br1118.91 (14)C30'—C29'—H29D109.5
C14—C15—Br1119.05 (15)C30'—C29'—H29E109.4
C15—C16—C17119.36 (17)H29D—C29'—H29E109.5
C15—C16—H16120.3C30'—C29'—H29F109.5
C17—C16—H16120.3H29D—C29'—H29F109.5
C16—C17—C12119.76 (17)H29E—C29'—H29F109.5
C16—C17—H17120.1O4'—C30'—N4'124.1 (16)
C12—C17—H17120.1O4'—C30'—C29'120.9 (18)
O2—C18—N2125.32 (17)N4'—C30'—C29'115.0 (12)
O2—C18—C4121.85 (17)N4'—C31'—H31D109.5
N2—C18—C4112.82 (16)N4'—C31'—H31E109.5
C24—C19—C20119.70 (17)H31D—C31'—H31E109.5
C24—C19—N2116.18 (17)N4'—C31'—H31F109.5
C20—C19—N2124.11 (17)H31D—C31'—H31F109.5
C21—C20—C19119.86 (18)H31E—C31'—H31F109.5
C21—C20—H20120.1N4'—C32'—H32D109.5
C19—C20—H20120.1N4'—C32'—H32E109.5
C22—C21—C20119.26 (18)H32D—C32'—H32E109.5
C22—C21—H21120.4N4'—C32'—H32F109.5
C20—C21—H21120.4H32D—C32'—H32F109.5
C21—C22—C23121.86 (17)H32E—C32'—H32F109.5
C9—C1—C2—C32.3 (3)C13—C12—C17—C160.9 (3)
C11—C1—C2—C3177.90 (18)N1—C12—C17—C16179.49 (16)
C1—C2—C3—C40.1 (3)C19—N2—C18—O24.7 (3)
C2—C3—C4—C102.3 (3)C19—N2—C18—C4174.05 (17)
C2—C3—C4—C18175.41 (18)C3—C4—C18—O2102.4 (2)
C10—C5—C6—C70.0 (3)C10—C4—C18—O275.2 (2)
C5—C6—C7—C80.2 (3)C3—C4—C18—N276.3 (2)
C6—C7—C8—C90.5 (3)C10—C4—C18—N2106.0 (2)
C7—C8—C9—C100.6 (3)C18—N2—C19—C24179.70 (19)
C7—C8—C9—C1179.19 (18)C18—N2—C19—C201.6 (3)
C2—C1—C9—C8176.20 (17)C24—C19—C20—C210.8 (3)
C11—C1—C9—C83.6 (3)N2—C19—C20—C21177.91 (17)
C2—C1—C9—C102.4 (3)C19—C20—C21—C220.3 (3)
C11—C1—C9—C10177.81 (17)C20—C21—C22—C231.5 (3)
C3—C4—C10—C5176.67 (18)C20—C21—C22—Br2179.05 (13)
C18—C4—C10—C55.7 (3)C21—C22—C23—C241.5 (3)
C3—C4—C10—C92.1 (3)Br2—C22—C23—C24179.00 (15)
C18—C4—C10—C9175.54 (17)C22—C23—C24—C190.4 (3)
C6—C5—C10—C4178.69 (18)C20—C19—C24—C230.7 (3)
C6—C5—C10—C90.1 (3)N2—C19—C24—C23178.07 (18)
C8—C9—C10—C4178.42 (17)C28—N3—C26—O34.5 (17)
C1—C9—C10—C40.2 (3)C27—N3—C26—O3174.0 (15)
C8—C9—C10—C50.4 (3)C28—N3—C26—C25175.8 (13)
C1—C9—C10—C5179.02 (17)C27—N3—C26—C256.4 (13)
C12—N1—C11—O13.9 (3)C28'—N3'—C26'—O3'1.5 (13)
C12—N1—C11—C1173.45 (16)C27'—N3'—C26'—O3'175.2 (12)
C2—C1—C11—O161.0 (2)C28'—N3'—C26'—C25'179.0 (12)
C9—C1—C11—O1118.8 (2)C27'—N3'—C26'—C25'4.3 (12)
C2—C1—C11—N1116.43 (19)O4—O4—C30—N40 (3)
C9—C1—C11—N163.8 (2)O4—O4—C30—C290 (4)
C11—N1—C12—C13162.24 (18)C31—N4—C30—O4174.5 (12)
C11—N1—C12—C1718.1 (3)C32—N4—C30—O40.1 (13)
C17—C12—C13—C141.1 (3)C31—N4—C30—O4174.5 (12)
N1—C12—C13—C14179.22 (16)C32—N4—C30—O40.1 (13)
C12—C13—C14—C150.2 (3)C31—N4—C30—C291.6 (9)
C13—C14—C15—C161.0 (3)C32—N4—C30—C29176.2 (9)
C13—C14—C15—Br1177.59 (14)C31'—N4'—C30'—O4'180 (2)
C14—C15—C16—C171.3 (3)C32'—N4'—C30'—O4'9 (2)
Br1—C15—C16—C17177.35 (13)C31'—N4'—C30'—C29'0.9 (17)
C15—C16—C17—C120.3 (3)C32'—N4'—C30'—C29'170.0 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O40.84 (2)2.03 (3)2.865 (13)170 (2)
N2—H2N···O3i0.81 (2)2.00 (3)2.797 (13)171 (2)
C2—H2···O1i0.952.503.423 (2)163
C6—H6···O2ii0.952.493.426 (2)169
C14—H14···O4iii0.952.553.48 (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 formulaC24H16Br2N2O2·2C4H9NO
Mr698.45
Crystal system, space groupTriclinic, 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)
V3)1554.3 (2)
Z2
Radiation typeMo Kα
µ (mm1)2.65
Crystal size (mm)0.47 × 0.33 × 0.17
Data collection
DiffractometerRigaku AFC10/Saturn724+
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.364, 0.637
No. of measured, independent and
observed [I > 2σ(I)] reflections
12655, 6836, 5420
Rint0.024
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.065, 0.95
No. of reflections6836
No. of parameters509
No. of restraints64
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N1—H1N···O40.84 (2)2.03 (3)2.865 (13)170 (2)
N2—H2N···O3'i0.81 (2)2.00 (3)2.797 (13)171 (2)
C2—H2···O1i0.952.503.423 (2)163
C6—H6···O2ii0.952.493.426 (2)169
C14—H14···O4iii0.952.553.48 (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

First citationFukuzumi, T., Tajiri, T., Tsukada, H. & Yoshida, J. (1994). Jpn Patent JP 06298919.
First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
First citationJing, L.-H. (2008). Acta Cryst. E64, o2379.  Web of Science CSD CrossRef IUCr Journals
First citationRigaku (2004). RAPID-AUTO. Rigaku/MSC Inc., The Woodlands, Texas, USA.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationTsukada, H., Tajiri, T., Fukuzumi, T. & Yoshida, J. (1994). Jpn Patent JP 06298918.

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