4,7-Diphenyl-2,9-bis­(trichloro­meth­yl)-1,10-phenanthroline

Xie, M.-H.; Liu, Y.-L.; Zou, P.; He, Y.-J.; Huang, B.

doi:10.1107/S1600536809051071

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o5

doi:10.1107/S1600536809051071

Open

access

4,7-Diphenyl-2,9-bis(trichloromethyl)-1,10-phenanthroline

Min-Hao Xie,^a Ya-Ling Liu,^a Pei Zou,^a Yong-Jun He ^a and Biao Huang ^a ^*

^aJiangsu Institute of Nuclear Medicine, Wuxi 214063, People's Republic of China
^*Correspondence e-mail: xiemh0704@sina.com

(Received 17 November 2009; accepted 26 November 2009; online 4 December 2009)

In the title compound, C₂₆H₁₄Cl₆N₂, the phenanthroline ring system is essentially planar, with an r.m.s. deviation of 0.048 (6) Å, and makes dihedral angles of 64.8 (14) and 66.6 (6)° with the two terminal phenyl rings. One of the trichloromethyl groups is disordered over two positions, with occupancies of 0.42 (2) and 0.58 (2).

Related literature

For 4,7-bis(chlorosulfophenyl)-1,10-phenanthroline-2,9-dicarboxylic acid, see: Evangelista et al. (1988 ); Papanastasiou-Diamandi et al. (1989 ); Scorilas & Diamandis (2000 ). For a related structure, see: Wang et al. (2007 ).

Experimental

Crystal data

C₂₆H₁₄Cl₆N₂
M_r = 567.09
Monoclinic, P 2₁ /c
a = 11.253 (2) Å
b = 19.789 (4) Å
c = 11.299 (2) Å
β = 106.544 (3)°
V = 2411.9 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.73 mm⁻¹
T = 133 K
0.30 × 0.27 × 0.20 mm

Data collection

Rigaku SPIDER diffractometer
Absorption correction: multi-scan (ABSCOR, Higashi, 1995 ) T_min = 0.810, T_max = 0.867
19334 measured reflections
5453 independent reflections
4573 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.080
S = 1.00
5453 reflections
335 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.31 e Å⁻³

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 I, global. DOI: 10.1107/S1600536809051071/is2495sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809051071/is2495Isup2.hkl

checkCIF report

Comment top

The molecule of the title complex (DDTP), (Fig.1), is an important intermediate for the synthesis of 4,7-bis(chlorosulfophenyl)-1,10- phenanthroline-2,9-dicarboxylic acid (BCPDA), a chelator that forms stable and highly fluorescent complexes with Eu³⁺ (Evangelista et al., 1988). BCPDA can be covalently incorporated into proteins under relatively mild conditions (Papanastasiou-Diamandi et al., 1989). and when complexes with Eu³⁺ forms a fluorescent product that has a lifetime in the range of 0.4 to 0.7 ms, it is useful for time-resolved fluorescence immunoassay applications (Scorilas & Diamandis, 2000). However, the crystal structure of DDTP has not been reported until now and therefore, we have determined its structure. In the crystal structure of the title compound, all bond lengths and angles are in good agreement with those observed in related compounds (Wang et al., 2007). The phenanthroline ring is planar to within 0.048 (6) Å. The dihedral angles between the terminal phenyl rings and the phenanthroline unit are 64.8 (14) and 66.6 (6)°.

Related literature top

For 4,7-bis(chlorosulfophenyl)-1,10-phenanthroline-2,9-dicarboxylic acid, see: Evangelista et al. (1988); Papanastasiou-Diamandi et al. (1989); Scorilas & Diamandis (2000). For a related structure, see: Wang et al. (2007).

Experimental top

4,7-Diphenyl-2,9-dimethyl-1,10-phenanthroline (0.5 mmol, 180.2 mg), N-chlorosuccinimide (3.3 mmol, 440.6 mg) and benzoyl peroxide (0.5 mg) were dissolved in carbon tetrachlorid (6 ml). The reaction mixture was refluxed for 6 h. After cooling to room temperature, the reaction mixture was filtered. The filtrate was concentrated in vacuo and the residue was dissolved in chlorobenzene (3 mL). The solution was evaporated in air affording colourless block-shaped crystals suitable for X-ray analysis (yield: 80.1%).

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. A view of the title compound with the atom-numbering scheme. Displacement ellipsoids were drawn at the 50% probability level and H atoms are represented as spheres of arbitrary radius.

4,7-Diphenyl-2,9-bis(trichloromethyl)-1,10-phenanthroline top

Crystal data top

C₂₆H₁₄Cl₆N₂	F(000) = 1144
M_r = 567.09	D_x = 1.562 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7807 reflections
a = 11.253 (2) Å	θ = 3.0–27.5°
b = 19.789 (4) Å	µ = 0.73 mm⁻¹
c = 11.299 (2) Å	T = 133 K
β = 106.544 (3)°	Block, colourless
V = 2411.9 (8) Å³	0.30 × 0.27 × 0.20 mm
Z = 4

Data collection top

Rigaku SPIDER diffractometer	5453 independent reflections
Radiation source: Rotating Anode	4573 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR, Higashi, 1995)	h = −14→14
T_min = 0.810, T_max = 0.867	k = −25→25
19334 measured reflections	l = −11→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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0386P)² + 0.845P] where P = (F_o² + 2F_c²)/3
5453 reflections	(Δ/σ)_max = 0.001
335 parameters	Δρ_max = 0.35 e Å⁻³
6 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₆H₁₄Cl₆N₂	V = 2411.9 (8) Å³
M_r = 567.09	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.253 (2) Å	µ = 0.73 mm⁻¹
b = 19.789 (4) Å	T = 133 K
c = 11.299 (2) Å	0.30 × 0.27 × 0.20 mm
β = 106.544 (3)°

Data collection top

Rigaku SPIDER diffractometer	5453 independent reflections
Absorption correction: multi-scan (ABSCOR, Higashi, 1995)	4573 reflections with I > 2σ(I)
T_min = 0.810, T_max = 0.867	R_int = 0.031
19334 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	6 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.00	Δρ_max = 0.35 e Å⁻³
5453 reflections	Δρ_min = −0.31 e Å⁻³
335 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)
Cl1	0.77991 (4)	0.20665 (2)	0.26183 (5)	0.03026 (12)
Cl2	0.87385 (4)	0.34261 (2)	0.28505 (4)	0.02826 (11)
Cl3	0.70433 (4)	0.29867 (3)	0.05663 (4)	0.03175 (12)
Cl4	0.8632 (9)	0.5763 (2)	0.7849 (9)	0.0382 (18)	0.42 (2)
Cl5	0.9336 (8)	0.4395 (4)	0.8454 (7)	0.0288 (11)	0.42 (2)
Cl6	0.9431 (4)	0.4847 (7)	0.6140 (4)	0.0361 (12)	0.42 (2)
Cl4'	0.8577 (6)	0.57471 (16)	0.7930 (5)	0.0220 (7)	0.58 (2)
Cl5'	0.9403 (6)	0.4374 (3)	0.8367 (6)	0.0398 (12)	0.58 (2)
Cl6'	0.9246 (6)	0.5098 (5)	0.6005 (4)	0.0377 (11)	0.58 (2)
N1	0.65388 (13)	0.35117 (7)	0.36420 (13)	0.0176 (3)
N2	0.69870 (13)	0.43350 (7)	0.56595 (13)	0.0189 (3)
C1	0.63101 (15)	0.31204 (8)	0.26646 (15)	0.0184 (3)
C2	0.51453 (16)	0.28295 (9)	0.20857 (16)	0.0206 (4)
H2	0.5027	0.2567	0.1357	0.025*
C3	0.41832 (15)	0.29307 (8)	0.25905 (16)	0.0187 (3)
C4	0.44090 (15)	0.33316 (8)	0.36810 (15)	0.0175 (3)
C5	0.34884 (15)	0.34379 (8)	0.43131 (15)	0.0186 (3)
H5	0.2690	0.3243	0.3993	0.022*
C6	0.37361 (15)	0.38123 (9)	0.53598 (15)	0.0189 (3)
H6	0.3113	0.3867	0.5770	0.023*
C7	0.49177 (15)	0.41274 (8)	0.58584 (15)	0.0177 (3)
C8	0.52306 (15)	0.44919 (9)	0.69909 (16)	0.0193 (3)
C9	0.63987 (16)	0.47611 (10)	0.74061 (16)	0.0237 (4)
H9	0.6642	0.5002	0.8164	0.028*
C10	0.72327 (16)	0.46772 (9)	0.66991 (16)	0.0212 (4)
C11	0.58475 (15)	0.40500 (8)	0.52455 (15)	0.0174 (3)
C12	0.55943 (15)	0.36274 (8)	0.41452 (15)	0.0167 (3)
C13	0.74181 (16)	0.29291 (9)	0.22063 (16)	0.0200 (4)
C14	0.85598 (15)	0.49422 (8)	0.72133 (13)	0.0259 (4)
C15	0.29361 (15)	0.26235 (8)	0.20141 (16)	0.0185 (3)
C16	0.22094 (17)	0.28428 (9)	0.08735 (16)	0.0244 (4)
H16	0.2510	0.3187	0.0447	0.029*
C17	0.10426 (18)	0.25642 (11)	0.03459 (19)	0.0320 (5)
H17	0.0548	0.2721	−0.0433	0.038*
C18	0.06033 (18)	0.20584 (11)	0.09570 (19)	0.0324 (5)
H18	−0.0195	0.1869	0.0602	0.039*
C19	0.13328 (19)	0.18308 (10)	0.20874 (18)	0.0308 (4)
H19	0.1039	0.1479	0.2504	0.037*
C20	0.24910 (18)	0.21126 (9)	0.26165 (17)	0.0259 (4)
H20	0.2983	0.1955	0.3396	0.031*
C21	0.43708 (15)	0.45433 (9)	0.77745 (15)	0.0186 (3)
C22	0.32389 (16)	0.48808 (9)	0.73897 (16)	0.0218 (4)
H22	0.2988	0.5088	0.6599	0.026*
C23	0.24798 (16)	0.49136 (10)	0.81640 (17)	0.0252 (4)
H23	0.1713	0.5149	0.7906	0.030*
C24	0.28335 (17)	0.46052 (10)	0.93113 (17)	0.0253 (4)
H24	0.2296	0.4616	0.9825	0.030*
C25	0.39631 (18)	0.42821 (10)	0.97102 (17)	0.0252 (4)
H25	0.4212	0.4079	1.0505	0.030*
C26	0.47359 (16)	0.42539 (9)	0.89462 (16)	0.0217 (4)
H26	0.5518	0.4036	0.9225	0.026*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0312 (2)	0.0216 (2)	0.0385 (3)	0.00736 (18)	0.0109 (2)	0.00183 (19)
Cl2	0.0198 (2)	0.0314 (2)	0.0348 (3)	−0.00346 (18)	0.00969 (19)	−0.00712 (19)
Cl3	0.0298 (2)	0.0472 (3)	0.0188 (2)	0.0067 (2)	0.00781 (19)	0.0009 (2)
Cl4	0.027 (2)	0.030 (2)	0.051 (4)	−0.0075 (14)	0.000 (2)	0.0095 (16)
Cl5	0.020 (2)	0.0270 (18)	0.032 (2)	0.0059 (11)	−0.0049 (14)	−0.0020 (12)
Cl6	0.0212 (9)	0.063 (3)	0.0263 (9)	−0.0124 (12)	0.0111 (8)	−0.0113 (14)
Cl4'	0.0240 (12)	0.0194 (11)	0.0206 (12)	−0.0074 (9)	0.0027 (9)	−0.0040 (9)
Cl5'	0.0176 (11)	0.0264 (13)	0.071 (3)	−0.0007 (9)	0.0053 (12)	−0.0114 (12)
Cl6'	0.0262 (11)	0.065 (2)	0.0277 (8)	−0.0212 (14)	0.0167 (8)	−0.0187 (10)
N1	0.0180 (7)	0.0173 (7)	0.0173 (7)	0.0013 (5)	0.0048 (6)	−0.0003 (6)
N2	0.0165 (7)	0.0230 (7)	0.0166 (7)	−0.0031 (6)	0.0037 (6)	−0.0025 (6)
C1	0.0188 (8)	0.0182 (8)	0.0181 (9)	0.0007 (6)	0.0050 (7)	0.0005 (7)
C2	0.0217 (9)	0.0206 (8)	0.0187 (9)	0.0002 (7)	0.0043 (7)	−0.0026 (7)
C3	0.0179 (8)	0.0157 (8)	0.0205 (9)	−0.0004 (6)	0.0024 (7)	0.0008 (7)
C4	0.0190 (8)	0.0157 (8)	0.0167 (8)	0.0008 (6)	0.0034 (7)	0.0013 (6)
C5	0.0158 (8)	0.0186 (8)	0.0201 (9)	−0.0020 (6)	0.0029 (7)	0.0012 (7)
C6	0.0174 (8)	0.0209 (8)	0.0185 (9)	0.0005 (6)	0.0054 (7)	0.0018 (7)
C7	0.0171 (8)	0.0185 (8)	0.0171 (9)	0.0002 (6)	0.0040 (7)	0.0013 (6)
C8	0.0180 (8)	0.0204 (8)	0.0195 (9)	−0.0003 (7)	0.0052 (7)	0.0003 (7)
C9	0.0212 (9)	0.0317 (10)	0.0178 (9)	−0.0057 (7)	0.0051 (7)	−0.0079 (7)
C10	0.0160 (8)	0.0276 (9)	0.0193 (9)	−0.0058 (7)	0.0041 (7)	−0.0031 (7)
C11	0.0172 (8)	0.0181 (8)	0.0162 (8)	−0.0008 (6)	0.0037 (6)	0.0014 (6)
C12	0.0179 (8)	0.0159 (8)	0.0154 (8)	0.0007 (6)	0.0031 (6)	0.0025 (6)
C13	0.0199 (8)	0.0210 (8)	0.0177 (9)	0.0010 (7)	0.0032 (7)	−0.0014 (7)
C14	0.0199 (9)	0.0382 (11)	0.0210 (10)	−0.0082 (8)	0.0079 (7)	−0.0083 (8)
C15	0.0175 (8)	0.0175 (8)	0.0208 (9)	−0.0016 (6)	0.0059 (7)	−0.0049 (7)
C16	0.0245 (9)	0.0252 (9)	0.0218 (9)	−0.0037 (7)	0.0038 (7)	−0.0008 (7)
C17	0.0262 (10)	0.0381 (11)	0.0262 (11)	−0.0041 (8)	−0.0017 (8)	−0.0020 (8)
C18	0.0225 (10)	0.0388 (12)	0.0356 (12)	−0.0122 (8)	0.0076 (8)	−0.0113 (9)
C19	0.0346 (11)	0.0278 (10)	0.0339 (11)	−0.0129 (8)	0.0161 (9)	−0.0035 (8)
C20	0.0284 (10)	0.0243 (9)	0.0235 (10)	−0.0031 (7)	0.0048 (8)	0.0009 (7)
C21	0.0185 (8)	0.0207 (8)	0.0173 (9)	−0.0043 (6)	0.0063 (7)	−0.0039 (7)
C22	0.0191 (9)	0.0255 (9)	0.0198 (9)	−0.0026 (7)	0.0040 (7)	0.0006 (7)
C23	0.0168 (8)	0.0292 (10)	0.0297 (10)	−0.0009 (7)	0.0067 (7)	−0.0046 (8)
C24	0.0232 (9)	0.0341 (10)	0.0223 (10)	−0.0089 (8)	0.0123 (7)	−0.0079 (8)
C25	0.0302 (10)	0.0291 (10)	0.0161 (9)	−0.0082 (8)	0.0063 (7)	−0.0007 (7)
C26	0.0199 (8)	0.0230 (9)	0.0210 (9)	−0.0005 (7)	0.0040 (7)	0.0002 (7)

Geometric parameters (Å, º) top

Cl1—C13	1.7890 (18)	C8—C21	1.489 (2)
Cl2—C13	1.7575 (18)	C9—C10	1.405 (2)
Cl3—C13	1.7831 (18)	C9—H9	0.9500
Cl4—C14	1.769 (3)	C10—C14	1.533 (2)
Cl5—C14	1.791 (3)	C11—C12	1.458 (2)
Cl6—C14	1.773 (3)	C15—C16	1.385 (2)
Cl4'—C14	1.784 (2)	C15—C20	1.389 (2)
Cl5'—C14	1.777 (2)	C16—C17	1.392 (3)
Cl6'—C14	1.777 (2)	C16—H16	0.9500
N1—C1	1.313 (2)	C17—C18	1.385 (3)
N1—C12	1.360 (2)	C17—H17	0.9500
N2—C10	1.315 (2)	C18—C19	1.382 (3)
N2—C11	1.356 (2)	C18—H18	0.9500
C1—C2	1.410 (2)	C19—C20	1.387 (3)
C1—C13	1.528 (2)	C19—H19	0.9500
C2—C3	1.375 (2)	C20—H20	0.9500
C2—H2	0.9500	C21—C26	1.393 (2)
C3—C4	1.426 (2)	C21—C22	1.394 (2)
C3—C15	1.498 (2)	C22—C23	1.388 (2)
C4—C12	1.414 (2)	C22—H22	0.9500
C4—C5	1.431 (2)	C23—C24	1.385 (3)
C5—C6	1.356 (2)	C23—H23	0.9500
C5—H5	0.9500	C24—C25	1.379 (3)
C6—C7	1.431 (2)	C24—H24	0.9500
C6—H6	0.9500	C25—C26	1.390 (2)
C7—C11	1.418 (2)	C25—H25	0.9500
C7—C8	1.423 (2)	C26—H26	0.9500
C8—C9	1.371 (2)

C1—N1—C12	117.49 (14)	Cl4—C14—Cl6	113.9 (4)
C10—N2—C11	117.37 (14)	C10—C14—Cl6'	110.97 (16)
N1—C1—C2	124.37 (15)	C10—C14—Cl5'	108.7 (2)
N1—C1—C13	116.60 (14)	Cl6'—C14—Cl5'	114.5 (4)
C2—C1—C13	118.83 (15)	C10—C14—Cl4'	111.2 (2)
C3—C2—C1	119.08 (16)	Cl6'—C14—Cl4'	104.1 (3)
C3—C2—H2	120.5	Cl5'—C14—Cl4'	107.3 (3)
C1—C2—H2	120.5	C10—C14—Cl5	107.2 (3)
C2—C3—C4	118.16 (15)	Cl4—C14—Cl5	106.4 (4)
C2—C3—C15	120.78 (15)	Cl6—C14—Cl5	103.3 (5)
C4—C3—C15	121.07 (15)	C16—C15—C20	118.96 (16)
C12—C4—C3	117.91 (15)	C16—C15—C3	120.62 (15)
C12—C4—C5	119.64 (15)	C20—C15—C3	120.42 (16)
C3—C4—C5	122.45 (15)	C15—C16—C17	120.63 (17)
C6—C5—C4	121.15 (15)	C15—C16—H16	119.7
C6—C5—H5	119.4	C17—C16—H16	119.7
C4—C5—H5	119.4	C18—C17—C16	120.00 (19)
C5—C6—C7	121.25 (16)	C18—C17—H17	120.0
C5—C6—H6	119.4	C16—C17—H17	120.0
C7—C6—H6	119.4	C19—C18—C17	119.60 (18)
C11—C7—C8	117.76 (15)	C19—C18—H18	120.2
C11—C7—C6	119.54 (15)	C17—C18—H18	120.2
C8—C7—C6	122.62 (15)	C18—C19—C20	120.34 (18)
C9—C8—C7	118.18 (15)	C18—C19—H19	119.8
C9—C8—C21	119.46 (15)	C20—C19—H19	119.8
C7—C8—C21	122.20 (15)	C19—C20—C15	120.47 (18)
C8—C9—C10	119.34 (16)	C19—C20—H20	119.8
C8—C9—H9	120.3	C15—C20—H20	119.8
C10—C9—H9	120.3	C26—C21—C22	119.32 (16)
N2—C10—C9	124.34 (16)	C26—C21—C8	118.11 (15)
N2—C10—C14	116.68 (14)	C22—C21—C8	122.55 (15)
C9—C10—C14	118.73 (14)	C23—C22—C21	119.86 (16)
N2—C11—C7	122.92 (15)	C23—C22—H22	120.1
N2—C11—C12	117.95 (14)	C21—C22—H22	120.1
C7—C11—C12	119.10 (15)	C24—C23—C22	120.34 (17)
N1—C12—C4	122.85 (15)	C24—C23—H23	119.8
N1—C12—C11	117.83 (14)	C22—C23—H23	119.8
C4—C12—C11	119.25 (15)	C25—C24—C23	120.19 (16)
C1—C13—Cl2	113.35 (12)	C25—C24—H24	119.9
C1—C13—Cl3	111.23 (12)	C23—C24—H24	119.9
Cl2—C13—Cl3	108.45 (9)	C24—C25—C26	119.82 (17)
C1—C13—Cl1	107.85 (12)	C24—C25—H25	120.1
Cl2—C13—Cl1	108.33 (9)	C26—C25—H25	120.1
Cl3—C13—Cl1	107.44 (9)	C25—C26—C21	120.42 (17)
C10—C14—Cl4	113.3 (4)	C25—C26—H26	119.8
C10—C14—Cl6	111.90 (18)	C21—C26—H26	119.8

C12—N1—C1—C2	1.9 (2)	C2—C1—C13—Cl2	170.74 (13)
C12—N1—C1—C13	−172.95 (14)	N1—C1—C13—Cl3	−136.63 (14)
N1—C1—C2—C3	−3.0 (3)	C2—C1—C13—Cl3	48.23 (19)
C13—C1—C2—C3	171.78 (15)	N1—C1—C13—Cl1	105.80 (15)
C1—C2—C3—C4	0.4 (2)	C2—C1—C13—Cl1	−69.34 (18)
C1—C2—C3—C15	−179.20 (15)	N2—C10—C14—Cl4	140.4 (4)
C2—C3—C4—C12	2.9 (2)	C9—C10—C14—Cl4	−45.1 (4)
C15—C3—C4—C12	−177.55 (15)	N2—C10—C14—Cl6	9.9 (5)
C2—C3—C4—C5	−176.69 (16)	C9—C10—C14—Cl6	−175.5 (5)
C15—C3—C4—C5	2.9 (2)	N2—C10—C14—Cl6'	28.8 (4)
C12—C4—C5—C6	−0.7 (2)	C9—C10—C14—Cl6'	−156.6 (4)
C3—C4—C5—C6	178.88 (16)	N2—C10—C14—Cl5'	−98.0 (3)
C4—C5—C6—C7	1.3 (3)	C9—C10—C14—Cl5'	76.6 (4)
C5—C6—C7—C11	0.3 (2)	N2—C10—C14—Cl4'	144.1 (3)
C5—C6—C7—C8	−176.41 (16)	C9—C10—C14—Cl4'	−41.3 (3)
C11—C7—C8—C9	1.7 (2)	N2—C10—C14—Cl5	−102.6 (4)
C6—C7—C8—C9	178.40 (17)	C9—C10—C14—Cl5	71.9 (4)
C11—C7—C8—C21	−173.61 (15)	C2—C3—C15—C16	−68.2 (2)
C6—C7—C8—C21	3.1 (3)	C4—C3—C15—C16	112.29 (19)
C7—C8—C9—C10	0.9 (3)	C2—C3—C15—C20	111.8 (2)
C21—C8—C9—C10	176.27 (17)	C4—C3—C15—C20	−67.8 (2)
C11—N2—C10—C9	0.5 (3)	C20—C15—C16—C17	1.0 (3)
C11—N2—C10—C14	174.73 (14)	C3—C15—C16—C17	−179.04 (17)
C8—C9—C10—N2	−2.1 (3)	C15—C16—C17—C18	−0.6 (3)
C8—C9—C10—C14	−176.22 (16)	C16—C17—C18—C19	−0.4 (3)
C10—N2—C11—C7	2.3 (2)	C17—C18—C19—C20	0.9 (3)
C10—N2—C11—C12	−175.49 (15)	C18—C19—C20—C15	−0.4 (3)
C8—C7—C11—N2	−3.4 (2)	C16—C15—C20—C19	−0.5 (3)
C6—C7—C11—N2	179.78 (15)	C3—C15—C20—C19	179.56 (17)
C8—C7—C11—C12	174.39 (15)	C9—C8—C21—C26	−59.3 (2)
C6—C7—C11—C12	−2.5 (2)	C7—C8—C21—C26	115.88 (19)
C1—N1—C12—C4	1.7 (2)	C9—C8—C21—C22	119.2 (2)
C1—N1—C12—C11	178.76 (15)	C7—C8—C21—C22	−65.6 (2)
C3—C4—C12—N1	−4.1 (2)	C26—C21—C22—C23	−1.3 (3)
C5—C4—C12—N1	175.48 (15)	C8—C21—C22—C23	−179.75 (16)
C3—C4—C12—C11	178.89 (15)	C21—C22—C23—C24	−0.8 (3)
C5—C4—C12—C11	−1.5 (2)	C22—C23—C24—C25	2.2 (3)
N2—C11—C12—N1	3.8 (2)	C23—C24—C25—C26	−1.4 (3)
C7—C11—C12—N1	−174.08 (15)	C24—C25—C26—C21	−0.7 (3)
N2—C11—C12—C4	−179.07 (15)	C22—C21—C26—C25	2.0 (3)
C7—C11—C12—C4	3.1 (2)	C8—C21—C26—C25	−179.40 (16)
N1—C1—C13—Cl2	−14.1 (2)

Experimental details

Crystal data
Chemical formula	C₂₆H₁₄Cl₆N₂
M_r	567.09
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	133
a, b, c (Å)	11.253 (2), 19.789 (4), 11.299 (2)
β (°)	106.544 (3)
V (Å³)	2411.9 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.73
Crystal size (mm)	0.30 × 0.27 × 0.20

Data collection
Diffractometer	Rigaku SPIDER diffractometer
Absorption correction	Multi-scan (ABSCOR, Higashi, 1995)
T_min, T_max	0.810, 0.867
No. of measured, independent and observed [I > 2σ(I)] reflections	19334, 5453, 4573
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.080, 1.00
No. of reflections	5453
No. of parameters	335
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.31

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

Acknowledgements

We acknowledge financial support by the National 863 Plan Foundation of China (grant No. 2008 A A10Z415), the Social Development Foundation of Jiangsu (grant No. BE2008633) and the Medical Research Project of Jiangsu (grant No. H200736).

References

Evangelista, R. A., Pollak, A., Allore, B., Templeton, E. F. & Morton, R. C. (1988). Clin. Biochem. 21, 173–178. CrossRef CAS PubMed Web of Science Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Papanastasiou-Diamandi, A., Conway, K. & Diamandis, E. P. (1989). J. Pharm. Sci. 78, 617–621. CrossRef CAS PubMed Web of Science Google Scholar
Rigaku (2004). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Scorilas, A. & Diamandis, E. P. (2000). Clin. Biochem. 33, 345–350. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, J., Ye, J.-W. & Wang, Y. (2007). Acta Cryst. E63, o2007–o2008. Web of Science CSD CrossRef IUCr Journals Google Scholar