2,9-Dichloro-1,10-phenanthroline.

The title mol-ecule, C(12)H(6)Cl(2)N(2), is almost planar (the r.m.s. deviation of C atoms is 0.04 Å). The C-N and C-C distances indicate delocalization of the π-electrons in the aromatic fused-ring system.

Related literature

For the synthesis, see: Yamada et al. (1990 ▶). The compound is used for the synthesis of other phenanthroline-like heterocycles; see: Hamilton et al. (2004 ▶); Ohira et al. (2005 ▶); Zong & Thummel (2004 ▶, 2005 ▶).

Experimental

Crystal data

C12H6Cl2N2

M = 249.09

Orthorhombic,

a = 19.4035 (3) Å

b = 4.4330 (1) Å

c = 11.7695 (2) Å

V = 1012.36 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.61 mm−1

T = 100 K

0.36 × 0.18 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.811, T max = 0.988

8646 measured reflections

2315 independent reflections

2248 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.061

S = 1.02

2315 reflections

145 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.16 e Å−3

Absolute structure: Flack (1983 ▶), 1097 Friedel pairs

Flack parameter: −0.01 (4)

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011180/tk2404sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011180/tk2404Isup2.hkl

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

C12H6Cl2N2	F(000) = 504
Mr = 249.09	Dx = 1.634 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5870 reflections
a = 19.4035 (3) Å	θ = 2.7–28.3°
b = 4.4330 (1) Å	µ = 0.61 mm−1
c = 11.7695 (2) Å	T = 100 K
V = 1012.36 (3) Å3	Plate, colourless
Z = 4	0.36 × 0.18 × 0.02 mm

Bruker SMART APEX diffractometer	2315 independent reflections
Radiation source: fine-focus sealed tube	2248 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→25
Tmin = 0.811, Tmax = 0.988	k = −5→5
8646 measured reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.022	H-atom parameters constrained
wR(F2) = 0.061	w = 1/[σ2(Fo2) + (0.0436P)2 + 0.147P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
2315 reflections	Δρmax = 0.27 e Å−3
145 parameters	Δρmin = −0.16 e Å−3
1 restraint	Absolute structure: Flack (1983), 1097 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.01 (4)

	x	y	z	Uiso*/Ueq
Cl1	0.027691 (18)	0.55270 (8)	0.25010 (3)	0.01876 (10)
Cl2	0.35805 (2)	0.89704 (8)	0.45699 (4)	0.02052 (10)
N1	0.11803 (7)	0.4349 (3)	0.40752 (11)	0.0151 (3)
N2	0.24727 (7)	0.5756 (3)	0.48930 (11)	0.0153 (3)
C1	0.05604 (8)	0.3672 (3)	0.37354 (12)	0.0158 (3)
C2	0.01038 (8)	0.1645 (4)	0.42492 (13)	0.0183 (3)
H2	−0.0341	0.1269	0.3945	0.022*
C3	0.03326 (8)	0.0226 (4)	0.52172 (14)	0.0184 (3)
H3	0.0046	−0.1192	0.5595	0.022*
C4	0.09941 (8)	0.0884 (3)	0.56464 (14)	0.0159 (3)
C5	0.14049 (8)	0.2979 (4)	0.50487 (12)	0.0150 (3)
C6	0.12494 (9)	−0.0487 (3)	0.66693 (14)	0.0178 (3)
H6	0.0980	−0.1968	0.7048	0.021*
C7	0.18689 (8)	0.0307 (4)	0.70984 (13)	0.0176 (3)
H7	0.2025	−0.0587	0.7785	0.021*
C8	0.22933 (8)	0.2478 (3)	0.65313 (13)	0.0158 (3)
C9	0.20767 (8)	0.3756 (3)	0.54864 (13)	0.0150 (3)
C10	0.29315 (8)	0.3417 (4)	0.69870 (14)	0.0189 (3)
H10	0.3088	0.2647	0.7695	0.023*
C11	0.33217 (9)	0.5458 (4)	0.63927 (14)	0.0195 (3)
H11	0.3752	0.6152	0.6676	0.023*
C12	0.30611 (7)	0.6483 (3)	0.53484 (13)	0.0164 (3)

	U11	U22	U33	U12	U13	U23
Cl1	0.01835 (17)	0.02130 (17)	0.01663 (17)	0.00087 (13)	−0.00441 (14)	−0.00032 (15)
Cl2	0.01900 (17)	0.02184 (16)	0.02072 (17)	−0.00573 (14)	0.00151 (15)	−0.00218 (15)
N1	0.0165 (6)	0.0163 (6)	0.0124 (6)	0.0010 (5)	0.0008 (5)	−0.0019 (5)
N2	0.0154 (6)	0.0158 (6)	0.0146 (6)	0.0001 (5)	0.0000 (5)	−0.0014 (4)
C1	0.0173 (7)	0.0174 (7)	0.0126 (7)	0.0046 (6)	−0.0004 (6)	−0.0028 (5)
C2	0.0154 (7)	0.0197 (7)	0.0199 (8)	0.0007 (6)	−0.0002 (6)	−0.0062 (6)
C3	0.0183 (8)	0.0186 (7)	0.0182 (8)	−0.0024 (6)	0.0051 (6)	−0.0023 (6)
C4	0.0192 (7)	0.0150 (7)	0.0136 (7)	0.0014 (5)	0.0028 (6)	−0.0030 (5)
C5	0.0158 (7)	0.0170 (7)	0.0121 (6)	0.0017 (5)	0.0013 (5)	−0.0018 (6)
C6	0.0220 (8)	0.0167 (7)	0.0146 (7)	0.0000 (6)	0.0060 (7)	0.0008 (6)
C7	0.0231 (8)	0.0177 (7)	0.0122 (6)	0.0047 (6)	0.0017 (6)	0.0004 (6)
C8	0.0181 (7)	0.0161 (7)	0.0132 (7)	0.0036 (6)	0.0001 (6)	−0.0022 (5)
C9	0.0178 (7)	0.0143 (6)	0.0130 (7)	0.0015 (5)	0.0014 (6)	−0.0027 (6)
C10	0.0212 (8)	0.0212 (8)	0.0145 (7)	0.0056 (6)	−0.0033 (6)	−0.0020 (6)
C11	0.0174 (8)	0.0223 (8)	0.0187 (8)	0.0003 (6)	−0.0041 (6)	−0.0052 (6)
C12	0.0156 (7)	0.0170 (7)	0.0166 (7)	−0.0003 (6)	0.0022 (6)	−0.0030 (6)

Cl1—C1	1.758 (2)	C4—C6	1.437 (2)
Cl2—C12	1.752 (2)	C5—C9	1.443 (2)
N1—C1	1.303 (2)	C6—C7	1.350 (2)
N1—C5	1.368 (2)	C6—H6	0.9500
N2—C12	1.302 (2)	C7—C8	1.432 (2)
N2—C9	1.365 (2)	C7—H7	0.9500
C1—C2	1.399 (2)	C8—C10	1.412 (2)
C2—C3	1.375 (2)	C8—C9	1.418 (2)
C2—H2	0.9500	C10—C11	1.372 (2)
C3—C4	1.410 (2)	C10—H10	0.9500
C3—H3	0.9500	C11—C12	1.405 (2)
C4—C5	1.412 (2)	C11—H11	0.9500
C1—N1—C5	116.68 (13)	C4—C6—H6	119.7
C12—N2—C9	116.36 (14)	C6—C7—C8	120.86 (14)
N1—C1—C2	126.86 (14)	C6—C7—H7	119.6
N1—C1—Cl1	115.78 (12)	C8—C7—H7	119.6
C2—C1—Cl1	117.36 (12)	C10—C8—C9	118.15 (14)
C3—C2—C1	116.59 (14)	C10—C8—C7	121.70 (14)
C3—C2—H2	121.7	C9—C8—C7	120.16 (14)
C1—C2—H2	121.7	N2—C9—C8	122.43 (14)
C2—C3—C4	119.74 (15)	N2—C9—C5	118.74 (14)
C2—C3—H3	120.1	C8—C9—C5	118.81 (14)
C4—C3—H3	120.1	C11—C10—C8	118.99 (15)
C3—C4—C5	118.14 (15)	C11—C10—H10	120.5
C3—C4—C6	121.77 (15)	C8—C10—H10	120.5
C5—C4—C6	120.08 (14)	C10—C11—C12	117.45 (15)
N1—C5—C4	121.97 (14)	C10—C11—H11	121.3
N1—C5—C9	118.72 (14)	C12—C11—H11	121.3
C4—C5—C9	119.29 (14)	N2—C12—C11	126.57 (15)
C7—C6—C4	120.66 (15)	N2—C12—Cl2	116.43 (12)
C7—C6—H6	119.7	C11—C12—Cl2	117.00 (12)
C5—N1—C1—C2	−1.3 (2)	C12—N2—C9—C8	−1.2 (2)
C5—N1—C1—Cl1	178.60 (10)	C12—N2—C9—C5	177.09 (13)
N1—C1—C2—C3	0.2 (2)	C10—C8—C9—N2	2.5 (2)
Cl1—C1—C2—C3	−179.66 (12)	C7—C8—C9—N2	−177.70 (13)
C1—C2—C3—C4	0.8 (2)	C10—C8—C9—C5	−175.77 (13)
C2—C3—C4—C5	−0.8 (2)	C7—C8—C9—C5	4.0 (2)
C2—C3—C4—C6	178.52 (14)	N1—C5—C9—N2	−2.1 (2)
C1—N1—C5—C4	1.3 (2)	C4—C5—C9—N2	179.17 (13)
C1—N1—C5—C9	−177.33 (14)	N1—C5—C9—C8	176.22 (13)
C3—C4—C5—N1	−0.4 (2)	C4—C5—C9—C8	−2.5 (2)
C6—C4—C5—N1	−179.63 (14)	C9—C8—C10—C11	−1.5 (2)
C3—C4—C5—C9	178.30 (14)	C7—C8—C10—C11	178.68 (15)
C6—C4—C5—C9	−1.0 (2)	C8—C10—C11—C12	−0.5 (2)
C3—C4—C6—C7	−176.22 (15)	C9—N2—C12—C11	−1.1 (2)
C5—C4—C6—C7	3.0 (2)	C9—N2—C12—Cl2	178.34 (10)
C4—C6—C7—C8	−1.5 (2)	C10—C11—C12—N2	2.0 (2)
C6—C7—C8—C10	177.72 (15)	C10—C11—C12—Cl2	−177.45 (12)
C6—C7—C8—C9	−2.1 (2)