10,12-Dimethyl-pteridino[6,7-f][1,10]phenanthroline-11,13(10H,12H)-dione-chloro-form (1/1).

In the title co-crystal, C(18)H(12)N(6)O(2)·CHCl(3), intra-molecular Cl(3)C-H⋯N hydrogen-bonding inter-actions occur between a single CHCl(3) and both N atoms at the 1,10-positions on the phenanthroline portion of the mol-ecule. The inter-planar distance between inversion-related mol-ecules is 3.241 (2) Å.

Related literature

For the synthesis, see: Black et al. (1993 ▶). For the possible use of metal complexes of this ligand as DNA probes, see: Gao et al. (2007 ▶); Lawrence et al. (2006 ▶). For studies involving the non-methyl­ated analog of the title compound, see: Chen et al. (2010 ▶); Dalton et al. (2008 ▶); Ozawa et al. (2006 ▶). For a related stucture, see: Ton & Bolte (2005 ▶). For Cl3C—H⋯N hydrogen bonding, see: Fan et al. (2009 ▶); Li & Wang (2007 ▶).

Experimental

Crystal data

C18H12N6O2·CHCl3

M = 463.70

Monoclinic,

a = 8.9043 (2) Å

b = 16.4009 (4) Å

c = 13.4872 (4) Å

β = 108.058 (1)°

V = 1872.63 (8) Å3

Z = 4

Cu Kα radiation

μ = 4.72 mm−1

T = 173 K

0.45 × 0.22 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: numerical (SADABS; Bruker, 2008 ▶) T min = 0.224, T max = 0.508

15543 measured reflections

3370 independent reflections

3115 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.095

S = 1.08

3370 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: APEX2 and SAINT (Bruker, 2008 ▶); data reduction: SAINT and XPREP (Bruker, 2008 ▶); 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: X-SEED.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536810031570/fl2311sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031570/fl2311Isup2.hkl

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

C18H12N6O2·CHCl3	F(000) = 944
Mr = 463.70	Dx = 1.645 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 8311 reflections
a = 8.9043 (2) Å	θ = 4.3–71.9°
b = 16.4009 (4) Å	µ = 4.72 mm−1
c = 13.4872 (4) Å	T = 173 K
β = 108.058 (1)°	Transparent prism, yellow
V = 1872.63 (8) Å3	0.45 × 0.22 × 0.17 mm
Z = 4

Bruker APEXII CCD diffractometer	3370 independent reflections
Radiation source: fine-focus sealed tube	3115 reflections with I > 2σ(I)
graphite	Rint = 0.033
phi and ω scans	θmax = 68.2°, θmin = 4.4°
Absorption correction: numerical (SADABS; Bruker, 2008)	h = −10→10
Tmin = 0.224, Tmax = 0.508	k = −19→19
15543 measured reflections	l = −16→15

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.061P)2 + 0.6946P] where P = (Fo2 + 2Fc2)/3
3370 reflections	(Δ/σ)max = 0.001
273 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.26 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
Cl1	1.11933 (6)	0.91490 (3)	0.06882 (4)	0.03314 (15)
Cl2	1.02227 (5)	0.75947 (3)	0.13113 (3)	0.02516 (14)
Cl3	0.78834 (5)	0.87388 (3)	0.00893 (4)	0.03132 (15)
O1	0.58359 (16)	0.89641 (8)	0.76117 (10)	0.0252 (3)
O2	0.50035 (16)	1.16797 (8)	0.78817 (10)	0.0253 (3)
N1	0.93260 (18)	0.83887 (9)	0.33300 (11)	0.0211 (3)
N2	0.69578 (17)	0.92402 (9)	0.59325 (11)	0.0185 (3)
N3	0.53018 (17)	1.03163 (9)	0.76877 (11)	0.0199 (3)
N4	0.61174 (18)	1.12873 (9)	0.66532 (11)	0.0193 (3)
N5	0.71061 (17)	1.08699 (9)	0.53254 (11)	0.0185 (3)
N6	0.94027 (18)	0.99643 (9)	0.27110 (11)	0.0206 (3)
C1	0.9330 (2)	0.76237 (11)	0.36516 (14)	0.0228 (4)
H1	0.9744	0.7215	0.3310	0.027*
C2	0.8759 (2)	0.73847 (11)	0.44641 (15)	0.0232 (4)
H2	0.8798	0.6829	0.4670	0.028*
C3	0.8141 (2)	0.79660 (11)	0.49591 (14)	0.0207 (4)
H3	0.7739	0.7820	0.5510	0.025*
C4	0.8113 (2)	0.87791 (10)	0.46354 (13)	0.0180 (3)
C5	0.7528 (2)	0.94334 (10)	0.51497 (13)	0.0181 (3)
C6	0.6493 (2)	0.98516 (11)	0.64097 (13)	0.0187 (4)
C7	0.5877 (2)	0.96493 (10)	0.72797 (13)	0.0193 (4)
C8	0.5445 (2)	1.11330 (11)	0.74324 (13)	0.0202 (4)
C9	0.6584 (2)	1.06698 (10)	0.61137 (13)	0.0185 (4)
C10	0.7584 (2)	1.02511 (10)	0.48401 (13)	0.0179 (3)
C11	0.8194 (2)	1.04465 (11)	0.39814 (13)	0.0186 (3)
C12	0.8254 (2)	1.12494 (11)	0.36400 (14)	0.0211 (4)
H12	0.7857	1.1686	0.3949	0.025*
C13	0.8895 (2)	1.13969 (11)	0.28512 (14)	0.0221 (4)
H13	0.8958	1.1936	0.2609	0.027*
C14	0.9452 (2)	1.07352 (11)	0.24152 (14)	0.0226 (4)
H14	0.9895	1.0843	0.1872	0.027*
C15	0.8776 (2)	0.98147 (10)	0.34867 (13)	0.0185 (3)
C16	0.8732 (2)	0.89648 (11)	0.38207 (13)	0.0181 (4)
C17	0.4656 (2)	1.01675 (11)	0.85485 (14)	0.0241 (4)
H17A	0.4159	0.9628	0.8465	0.036*
H17B	0.3867	1.0586	0.8543	0.036*
H17C	0.5511	1.0189	0.9213	0.036*
C18	0.6292 (2)	1.21489 (11)	0.64044 (14)	0.0232 (4)
H18A	0.7078	1.2195	0.6034	0.035*
H18B	0.6641	1.2466	0.7051	0.035*
H18C	0.5275	1.2359	0.5962	0.035*
C19	0.9722 (2)	0.86285 (11)	0.10784 (14)	0.0226 (4)
H19	0.9645	0.8881	0.1736	0.027*

	U11	U22	U33	U12	U13	U23
Cl1	0.0291 (3)	0.0310 (3)	0.0357 (3)	−0.00401 (19)	0.0049 (2)	0.01122 (19)
Cl2	0.0350 (3)	0.0176 (2)	0.0227 (2)	0.00243 (17)	0.00862 (19)	0.00046 (15)
Cl3	0.0251 (3)	0.0264 (3)	0.0357 (3)	0.00431 (18)	−0.0004 (2)	−0.00619 (18)
O1	0.0364 (7)	0.0162 (6)	0.0245 (7)	−0.0019 (5)	0.0115 (6)	−0.0004 (5)
O2	0.0348 (7)	0.0187 (6)	0.0233 (6)	0.0043 (5)	0.0104 (6)	−0.0023 (5)
N1	0.0255 (8)	0.0172 (7)	0.0193 (7)	−0.0007 (6)	0.0048 (6)	−0.0020 (6)
N2	0.0213 (7)	0.0153 (7)	0.0167 (7)	−0.0020 (6)	0.0023 (6)	−0.0017 (5)
N3	0.0240 (7)	0.0175 (7)	0.0179 (7)	−0.0003 (6)	0.0059 (6)	−0.0019 (5)
N4	0.0258 (8)	0.0133 (7)	0.0179 (7)	0.0018 (6)	0.0054 (6)	−0.0010 (5)
N5	0.0213 (7)	0.0146 (7)	0.0170 (7)	0.0009 (5)	0.0023 (6)	0.0001 (5)
N6	0.0255 (8)	0.0180 (7)	0.0168 (7)	−0.0011 (6)	0.0042 (6)	0.0004 (6)
C1	0.0286 (9)	0.0162 (9)	0.0228 (9)	0.0007 (7)	0.0067 (8)	−0.0030 (7)
C2	0.0296 (9)	0.0141 (8)	0.0244 (9)	0.0000 (7)	0.0065 (8)	0.0000 (7)
C3	0.0239 (9)	0.0179 (9)	0.0189 (8)	−0.0021 (7)	0.0047 (7)	−0.0011 (7)
C4	0.0194 (8)	0.0150 (8)	0.0165 (8)	−0.0018 (6)	0.0011 (7)	−0.0015 (6)
C5	0.0194 (8)	0.0161 (8)	0.0159 (8)	−0.0021 (7)	0.0015 (7)	−0.0014 (6)
C6	0.0201 (8)	0.0168 (8)	0.0167 (8)	−0.0007 (7)	0.0019 (7)	−0.0014 (6)
C7	0.0227 (8)	0.0164 (9)	0.0164 (8)	−0.0023 (7)	0.0025 (7)	−0.0026 (6)
C8	0.0221 (9)	0.0183 (8)	0.0172 (8)	0.0007 (7)	0.0018 (7)	−0.0006 (7)
C9	0.0193 (8)	0.0164 (8)	0.0165 (8)	−0.0002 (7)	0.0006 (7)	−0.0021 (6)
C10	0.0184 (8)	0.0161 (8)	0.0163 (8)	−0.0001 (6)	0.0011 (7)	−0.0017 (6)
C11	0.0198 (8)	0.0168 (8)	0.0161 (8)	−0.0002 (7)	0.0012 (7)	0.0006 (6)
C12	0.0228 (9)	0.0172 (9)	0.0198 (9)	0.0009 (7)	0.0015 (7)	−0.0010 (7)
C13	0.0256 (9)	0.0175 (8)	0.0201 (9)	−0.0015 (7)	0.0024 (7)	0.0033 (7)
C14	0.0266 (9)	0.0209 (9)	0.0187 (8)	−0.0027 (7)	0.0047 (7)	0.0017 (7)
C15	0.0206 (8)	0.0163 (9)	0.0154 (8)	−0.0007 (7)	0.0008 (7)	−0.0003 (6)
C16	0.0193 (8)	0.0158 (8)	0.0156 (8)	−0.0006 (7)	0.0000 (7)	−0.0018 (6)
C17	0.0314 (10)	0.0217 (9)	0.0210 (9)	−0.0015 (7)	0.0105 (8)	−0.0015 (7)
C18	0.0339 (10)	0.0139 (8)	0.0218 (9)	0.0014 (7)	0.0084 (8)	−0.0002 (7)
C19	0.0264 (9)	0.0191 (8)	0.0197 (9)	−0.0006 (7)	0.0036 (7)	−0.0005 (7)

Cl1—C19	1.7747 (18)	C3—C4	1.401 (2)
Cl2—C19	1.7564 (18)	C3—H3	0.9500
Cl3—C19	1.7716 (19)	C4—C16	1.407 (2)
O1—C7	1.214 (2)	C4—C5	1.459 (2)
O2—C8	1.214 (2)	C5—C10	1.410 (2)
N1—C1	1.327 (2)	C6—C9	1.410 (2)
N1—C16	1.352 (2)	C6—C7	1.479 (2)
N2—C6	1.325 (2)	C10—C11	1.459 (2)
N2—C5	1.343 (2)	C11—C12	1.401 (2)
N3—C7	1.392 (2)	C11—C15	1.415 (2)
N3—C8	1.399 (2)	C12—C13	1.376 (3)
N3—C17	1.467 (2)	C12—H12	0.9500
N4—C9	1.384 (2)	C13—C14	1.396 (3)
N4—C8	1.384 (2)	C13—H13	0.9500
N4—C18	1.472 (2)	C14—H14	0.9500
N5—C9	1.327 (2)	C15—C16	1.469 (2)
N5—C10	1.346 (2)	C17—H17A	0.9800
N6—C14	1.331 (2)	C17—H17B	0.9800
N6—C15	1.352 (2)	C17—H17C	0.9800
C1—C2	1.399 (3)	C18—H18A	0.9800
C1—H1	0.9500	C18—H18B	0.9800
C2—C3	1.373 (3)	C18—H18C	0.9800
C2—H2	0.9500	C19—H19	1.0000
C1—N1—C16	117.55 (15)	N5—C10—C11	118.16 (15)
C6—N2—C5	117.01 (15)	C5—C10—C11	120.02 (15)
C7—N3—C8	125.62 (15)	C12—C11—C15	118.44 (16)
C7—N3—C17	117.70 (15)	C12—C11—C10	121.93 (16)
C8—N3—C17	116.25 (14)	C15—C11—C10	119.62 (15)
C9—N4—C8	122.44 (15)	C13—C12—C11	119.12 (16)
C9—N4—C18	120.82 (14)	C13—C12—H12	120.4
C8—N4—C18	116.73 (14)	C11—C12—H12	120.4
C9—N5—C10	116.45 (15)	C12—C13—C14	118.39 (16)
C14—N6—C15	117.66 (15)	C12—C13—H13	120.8
N1—C1—C2	123.77 (16)	C14—C13—H13	120.8
N1—C1—H1	118.1	N6—C14—C13	124.28 (16)
C2—C1—H1	118.1	N6—C14—H14	117.9
C3—C2—C1	118.95 (17)	C13—C14—H14	117.9
C3—C2—H2	120.5	N6—C15—C11	122.09 (16)
C1—C2—H2	120.5	N6—C15—C16	117.76 (15)
C2—C3—C4	118.70 (16)	C11—C15—C16	120.14 (15)
C2—C3—H3	120.7	N1—C16—C4	122.58 (16)
C4—C3—H3	120.7	N1—C16—C15	117.50 (15)
C3—C4—C16	118.44 (16)	C4—C16—C15	119.91 (15)
C3—C4—C5	121.75 (15)	N3—C17—H17A	109.5
C16—C4—C5	119.76 (16)	N3—C17—H17B	109.5
N2—C5—C10	120.93 (16)	H17A—C17—H17B	109.5
N2—C5—C4	118.54 (15)	N3—C17—H17C	109.5
C10—C5—C4	120.52 (15)	H17A—C17—H17C	109.5
N2—C6—C9	121.92 (16)	H17B—C17—H17C	109.5
N2—C6—C7	117.64 (16)	N4—C18—H18A	109.5
C9—C6—C7	120.43 (16)	N4—C18—H18B	109.5
O1—C7—N3	121.63 (16)	H18A—C18—H18B	109.5
O1—C7—C6	124.15 (16)	N4—C18—H18C	109.5
N3—C7—C6	114.20 (15)	H18A—C18—H18C	109.5
O2—C8—N4	121.82 (16)	H18B—C18—H18C	109.5
O2—C8—N3	121.06 (16)	Cl2—C19—Cl3	110.94 (10)
N4—C8—N3	117.12 (15)	Cl2—C19—Cl1	110.33 (10)
N5—C9—N4	118.51 (16)	Cl3—C19—Cl1	108.81 (10)
N5—C9—C6	121.85 (16)	Cl2—C19—H19	108.9
N4—C9—C6	119.65 (16)	Cl3—C19—H19	108.9
N5—C10—C5	121.81 (16)	Cl1—C19—H19	108.9
C16—N1—C1—C2	−0.1 (3)	N2—C6—C9—N5	1.6 (3)
N1—C1—C2—C3	0.7 (3)	C7—C6—C9—N5	−178.85 (16)
C1—C2—C3—C4	−0.4 (3)	N2—C6—C9—N4	−178.51 (16)
C2—C3—C4—C16	−0.5 (3)	C7—C6—C9—N4	1.0 (3)
C2—C3—C4—C5	−177.73 (17)	C9—N5—C10—C5	0.3 (2)
C6—N2—C5—C10	−1.6 (2)	C9—N5—C10—C11	−178.90 (15)
C6—N2—C5—C4	177.43 (15)	N2—C5—C10—N5	1.4 (3)
C3—C4—C5—N2	−2.1 (3)	C4—C5—C10—N5	−177.55 (16)
C16—C4—C5—N2	−179.32 (15)	N2—C5—C10—C11	−179.40 (15)
C3—C4—C5—C10	176.93 (16)	C4—C5—C10—C11	1.6 (3)
C16—C4—C5—C10	−0.3 (3)	N5—C10—C11—C12	−1.6 (3)
C5—N2—C6—C9	0.1 (3)	C5—C10—C11—C12	179.22 (16)
C5—N2—C6—C7	−179.42 (15)	N5—C10—C11—C15	177.03 (16)
C8—N3—C7—O1	173.01 (17)	C5—C10—C11—C15	−2.2 (2)
C17—N3—C7—O1	0.8 (3)	C15—C11—C12—C13	−1.0 (3)
C8—N3—C7—C6	−8.3 (2)	C10—C11—C12—C13	177.63 (16)
C17—N3—C7—C6	179.50 (15)	C11—C12—C13—C14	0.5 (3)
N2—C6—C7—O1	3.3 (3)	C15—N6—C14—C13	−0.2 (3)
C9—C6—C7—O1	−176.22 (17)	C12—C13—C14—N6	0.1 (3)
N2—C6—C7—N3	−175.31 (15)	C14—N6—C15—C11	−0.3 (3)
C9—C6—C7—N3	5.1 (2)	C14—N6—C15—C16	−179.49 (15)
C9—N4—C8—O2	−178.08 (16)	C12—C11—C15—N6	1.0 (3)
C18—N4—C8—O2	0.8 (3)	C10—C11—C15—N6	−177.72 (16)
C9—N4—C8—N3	2.3 (3)	C12—C11—C15—C16	−179.93 (16)
C18—N4—C8—N3	−178.82 (15)	C10—C11—C15—C16	1.4 (2)
C7—N3—C8—O2	−174.77 (17)	C1—N1—C16—C4	−0.8 (3)
C17—N3—C8—O2	−2.5 (2)	C1—N1—C16—C15	178.08 (16)
C7—N3—C8—N4	4.9 (3)	C3—C4—C16—N1	1.1 (3)
C17—N3—C8—N4	177.20 (15)	C5—C4—C16—N1	178.42 (15)
C10—N5—C9—N4	178.39 (15)	C3—C4—C16—C15	−177.78 (16)
C10—N5—C9—C6	−1.7 (2)	C5—C4—C16—C15	−0.5 (3)
C8—N4—C9—N5	174.92 (15)	N6—C15—C16—N1	0.1 (2)
C18—N4—C9—N5	−4.0 (2)	C11—C15—C16—N1	−179.05 (15)
C8—N4—C9—C6	−5.0 (3)	N6—C15—C16—C4	179.05 (15)
C18—N4—C9—C6	176.14 (16)	C11—C15—C16—C4	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···N1	1.00	2.39	3.188 (2)	136.
C19—H19···N6	1.00	2.26	3.181 (2)	152.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯N1	1.00	2.39	3.188 (2)	136
C19—H19⋯N6	1.00	2.26	3.181 (2)	152