4,7-Diphenyl-2,9-bis-(trichloro-meth-yl)-1,10-phenanthroline.

In the title compound, C(26)H(14)Cl(6)N(2), 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 trichloro-methyl 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 = 567.09

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.080

S = 1.00

5453 reflections

335 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809051071/is2495sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H14Cl6N2	F(000) = 1144
Mr = 567.09	Dx = 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

Rigaku SPIDER diffractometer	5453 independent reflections
Radiation source: Rotating Anode	4573 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR, Higashi, 1995)	h = −14→14
Tmin = 0.810, Tmax = 0.867	k = −25→25
19334 measured reflections	l = −11→14

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(Fo2) + (0.0386P)2 + 0.845P] where P = (Fo2 + 2Fc2)/3
5453 reflections	(Δ/σ)max = 0.001
335 parameters	Δρmax = 0.35 e Å−3
6 restraints	Δρmin = −0.31 e Å−3

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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)