7,9-Dichloro-6H,12H-indolo[2,1-b]quinazoline-6,12-dione

Grundt, P.; Douglas, K.A.; Krivogorsky, B.; Nemykin, V.N.

doi:10.1107/S1600536810018969

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 6| June 2010| Pages o1474-o1475

https://doi.org/10.1107/S1600536810018969

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7,9-Dichloro-6H,12H-indolo[2,1-b]quinazoline-6,12-dione

Peter Grundt,^a Kelsi A. Douglas,^a Bogdana Krivogorsky ^a and Victor N. Nemykin ^a ^*

^aDepartment of Chemistry & Biochemistry, University of Minnesota Duluth, 1039 University Drive, Duluth, MN 55812, USA
^*Correspondence e-mail: pgrundt@d.umn.edu, vnemykin@d.umn.edu

(Received 10 May 2010; accepted 20 May 2010; online 29 May 2010)

There are two independent molecules in the asymmetric unit of the title compound, C₁₅H₆Cl₂N₂O₂. The conjugated four-ring system is essentially planar in each molecule [maximum deviation = 0.089 (2) Å]. In the crystal, weak intermolecular C—H⋯Cl, C—H⋯O and C—H⋯·N interactions help to stabilize the packing.

Related literature

For the synthesis, chemistry, and biological activity of the title compound see: Krivogorsky et al. (2008 ). For chemistry and biological activity of the natural product tryptanthrin (indolo[2,1-b]quinazoline-6,12-dione) and its derivatives and for related structures, see: Honda et al. (1979 ); Mitscher & Baker (1998 ); Kataoka et al. (2001 ); Bandekar et al. (2010 ); Sharma et al. (2002 ); Motoki et al. (2005 ); Yu et al. (2009 ); Bhattacharjee et al. (2002 ); Scovill et al. (2002 ); Bhattacharjee et al. (2004 ); Pitzer et al. (2000 ). For the extinction correction, see: Larson (1970 ).

Experimental

Crystal data

C₁₅H₆Cl₂N₂O₂
M_r = 317.13
Triclinic, $[P \overline 1]$
a = 7.0179 (2) Å
b = 10.7276 (3) Å
c = 17.2338 (12) Å
α = 94.908 (7)°
β = 96.709 (7)°
γ = 107.395 (8)°
V = 1219.66 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.54 mm⁻¹
T = 100 K
0.54 × 0.48 × 0.35 mm

Data collection

Rigaku R-AXIS RAPID-II imaging plate diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.633, T_max = 0.899
31502 measured reflections
5585 independent reflections
4830 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.082
S = 1.00
5571 reflections
416 parameters
84 restraints
All H-atom parameters refined
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1B—H1B⋯Cl1Aⁱ	0.94 (2)	2.73 (2)	3.637 (2)	162 (1)
C2A—H2A⋯O1Bⁱⁱ	0.93 (2)	2.54 (2)	3.264 (3)	135 (1)
C4B—H4B⋯N5Aⁱⁱⁱ	0.94 (2)	2.56 (2)	3.422 (3)	154 (1)
C10A—H6A⋯Cl2B^iv	0.94 (2)	2.67 (2)	3.585 (2)	165 (1)
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+2, -y, -z; (iii) x-1, y, z; (iv) x, y-1, z-1.

Data collection: CrystalClear (Rigaku Americas, 2009 ); cell refinement: HKL-2000 (Otwinowski & Minor, 1997 ); data reduction: CrystalClear; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ); molecular graphics: CAMERON (Watkin et al., 1996 ); software used to prepare material for publication: CRYSTALS.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810018969/jj2032sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810018969/jj2032Isup2.hkl

checkCIF report

Comment top

The natural product tryptanthrin (indolo[2,1-b]quinazoline-6,12-dione) and its derivatives have been shown to possess antibacterial (Honda et al., 1979), Mitscher & Baker, 1998, Kataoka et al., 2001, Bandekar et al., 2010) and antitumor Sharma et al., 2002, Motoki et al., 2005, Yu et al., 2009) properties. Of particular interest is the discovery by several groups that this class of compounds also inibits the growth of parasites such as Leishmania donovani (Bhattacharjee et al., 2002), Trypanosoma brucei (Scovill et al., 2002), and Plasmodium falciparum (Bhattacharjee et al., 2004, Pitzer et al., 2000), and more recently by our laboratory, Toxoplasma gondii (Krivogorsky et al., 2008). In our continued interest to characterize the structure-activity-relationship of this class of compounds and to reveal the underlying mechanism, we have synthesized the 7,9-dichloro analog of tryptanthrin.

The title compound, (I), C₁₅H₆Cl₂N₂O₂, crystallizes in the P-1 space group with two independent molecules in the asymmetric unit cell. It consists of a 7,9-dichloroindolo ring fused to a quinazoline ring with a dione group at the 6 and 12 poisitions (IUPAC nomenclature). C—Cl bond distances have been observed between 1.7272 (19) and 1.7358 (19) Å with Cl1—C7 distances being slightly shorter as compared to Cl2—C9 bond lengths. C=O bonds have clear double bond character and were observed between 1.211 (2) and 1.221 (2) Å with C=O bonds in the five-membered ring being slightly shorter as compared to those at the six-membered rings. N5—C14 bond distances in molecules A and B have clear double bond character. Four weak intermolecular interactions are observed in (I), (Table 2) that help stabilize crystal packing.

Related literature top

For the synthesis, chemistry, and biological activity of the title compound see: Krivogorsky et al. (2008). For chemistry and biological activity of the natural product tryptanthrin (indolo[2,1-b]quinazoline-6,12-dione) and its derivatives and for related structures, see: Honda et al. (1979); Mitscher & Baker (1998); Kataoka et al. (2001); Bandekar et al. (2010); Sharma et al. (2002); Motoki et al. (2005); Yu et al. (2009); Bhattacharjee et al. (2002); Scovill et al. (2002); Bhattacharjee et al. (2004); Pitzer et al. (2000). For the extinction correction, see: Larson (1970).

Experimental top

The title compound was prepared by condensation of isatoic anhydride and 4,6-dichloroisatin in refluxing benzene with triethylamine as a co-solvent (Krivogorsky et al., 2008). Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of an acetone solution of the compound.

Structure description top

For the synthesis, chemistry, and biological activity of the title compound see: Krivogorsky et al. (2008). For chemistry and biological activity of the natural product tryptanthrin (indolo[2,1-b]quinazoline-6,12-dione) and its derivatives and for related structures, see: Honda et al. (1979); Mitscher & Baker (1998); Kataoka et al. (2001); Bandekar et al. (2010); Sharma et al. (2002); Motoki et al. (2005); Yu et al. (2009); Bhattacharjee et al. (2002); Scovill et al. (2002); Bhattacharjee et al. (2004); Pitzer et al. (2000). For the extinction correction, see: Larson (1970).

Computing details top

Data collection: CrystalClear (Rigaku Americas, 2009); cell refinement: HKL-2000 (Otwinowski & Minor, 1997); data reduction: CrystalClear (Rigaku Americas, 2009); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Figures top

	Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius.
	Fig. 2. Packing diagram for the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are omited for clarity.

7,9-Dichloro-6H,12H-indolo[2,1-b]quinazoline-6,12-dione top

Crystal data top

C₁₅H₆Cl₂N₂O₂	Z = 4
M_r = 317.13	F(000) = 640
Triclinic, P1	D_x = 1.727 Mg m⁻³
Hall symbol: -P 1	Melting point: 200 K
a = 7.0179 (2) Å	Mo Kα radiation, λ = 0.71075 Å
b = 10.7276 (3) Å	Cell parameters from 28356 reflections
c = 17.2338 (12) Å	θ = 3.1–27.5°
α = 94.908 (7)°	µ = 0.54 mm⁻¹
β = 96.709 (7)°	T = 100 K
γ = 107.395 (8)°	Block, yellow
V = 1219.66 (12) Å³	0.54 × 0.48 × 0.35 mm

Data collection top

Rigaku R-AXIS RAPID-II imaging plate diffractometer	5585 independent reflections
Radiation source: Sealed tube (Mo)	4830 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
Detector resolution: 10 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −9→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −13→13
T_min = 0.633, T_max = 0.899	l = −22→22
31502 measured reflections

Refinement top

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)] = 0.034	All H-atom parameters refined
wR(F²) = 0.082	Method = Modified Sheldrick w = 1/[σ²(F²) + (0.02P)² + 2.09P], where P = [max(F_o²,0) + 2F_c²]/3
S = 1.00	(Δ/σ)_max = 0.001
5571 reflections	Δρ_max = 0.53 e Å⁻³
416 parameters	Δρ_min = −0.36 e Å⁻³
84 restraints	Extinction correction: Larson (1970), Equation 22
0 constraints	Extinction coefficient: 43 (4)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₅H₆Cl₂N₂O₂	γ = 107.395 (8)°
M_r = 317.13	V = 1219.66 (12) Å³
Triclinic, P1	Z = 4
a = 7.0179 (2) Å	Mo Kα radiation
b = 10.7276 (3) Å	µ = 0.54 mm⁻¹
c = 17.2338 (12) Å	T = 100 K
α = 94.908 (7)°	0.54 × 0.48 × 0.35 mm
β = 96.709 (7)°

Data collection top

Rigaku R-AXIS RAPID-II imaging plate diffractometer	5585 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4830 reflections with I > 2σ(I)
T_min = 0.633, T_max = 0.899	R_int = 0.049
31502 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	84 restraints
wR(F²) = 0.082	All H-atom parameters refined
S = 1.00	Δρ_max = 0.53 e Å⁻³
5571 reflections	Δρ_min = −0.36 e Å⁻³
416 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an X-stream 2000 liquid nitrogen generator with open-flow nitrogen cryostat with a nominal stability of 0.1 K. ¹H NMR (DMSO-d6, 500 MHz): d 7.75-7.78 (m, 2H), 7.98-8.00 (m, 2H), 8.33 (d, J 7.5, 1H), 8.41 (d, J 1.9, 1H). ¹³C NMR (DMSO-d6, 125 MHz): d 115.6, 118.3, 122.6, 127.0, 127.4, 129.9, 130.1, 132.3, 135.6, 141.6, 144.4, 146.1, 147.3, 157.6, 178.4.

Refinement. Crystals for Windows program eliminates all reflections with [Sin theta/lambda]**2 less than 0.01 in order to eliminate reflections that may be poorly measured in the vicinity of the beam stop. Such filter eliminated 14 reflections, which resulted in difference between 5585 measured unique reflections and 5571 reflections used for refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1A	0.12767 (7)	0.19849 (5)	−0.30745 (3)	0.0154
Cl2A	0.22470 (8)	−0.16786 (5)	−0.51632 (3)	0.0203
O1A	0.5092 (2)	0.25603 (14)	−0.16905 (8)	0.0172
O2A	0.8111 (2)	−0.15104 (14)	−0.30107 (8)	0.0181
C1A	1.1319 (3)	−0.08669 (19)	−0.17069 (12)	0.0162
C2A	1.2819 (3)	−0.0485 (2)	−0.10617 (12)	0.0183
C3A	1.2850 (3)	0.0523 (2)	−0.04843 (12)	0.0208
C4A	1.1391 (3)	0.1145 (2)	−0.05462 (12)	0.0185
N5A	0.8403 (2)	0.14280 (16)	−0.12490 (10)	0.0151
C6A	0.5402 (3)	0.16629 (19)	−0.20790 (11)	0.0137
C7A	0.2640 (3)	0.09548 (18)	−0.33341 (11)	0.0137
C8A	0.1974 (3)	0.01396 (19)	−0.40464 (11)	0.0154
C9A	0.3055 (3)	−0.06961 (19)	−0.42595 (11)	0.0151
C10A	0.4729 (3)	−0.07980 (19)	−0.37831 (11)	0.0146
N11A	0.6952 (2)	0.01079 (16)	−0.24828 (9)	0.0130
C12A	0.8273 (3)	−0.06404 (19)	−0.24787 (11)	0.0140
C13A	0.9855 (3)	0.07665 (19)	−0.11960 (11)	0.0142
C14A	0.7090 (3)	0.10816 (18)	−0.18691 (11)	0.0134
C15A	0.4331 (3)	0.09159 (18)	−0.28464 (11)	0.0129
C16A	0.5321 (3)	0.00196 (19)	−0.30772 (11)	0.0141
C17A	0.9828 (3)	−0.02472 (18)	−0.17809 (11)	0.0139
Cl1B	0.89170 (7)	0.34858 (5)	0.34019 (3)	0.0173
Cl2B	0.70190 (7)	0.70635 (5)	0.52404 (3)	0.0192
O1B	0.5337 (2)	0.26130 (14)	0.19080 (9)	0.0189
O2B	0.1512 (2)	0.64871 (14)	0.28391 (8)	0.0169
C1B	−0.1458 (3)	0.55847 (19)	0.14382 (12)	0.0163
C2B	−0.2819 (3)	0.5080 (2)	0.07583 (12)	0.0193
C3B	−0.2635 (3)	0.4038 (2)	0.02547 (12)	0.0192
C4B	−0.1086 (3)	0.3521 (2)	0.04302 (12)	0.0176
N5B	0.1872 (3)	0.34718 (16)	0.12667 (10)	0.0153
C6B	0.4831 (3)	0.34864 (19)	0.22288 (11)	0.0148
C7B	0.7333 (3)	0.44170 (19)	0.35489 (12)	0.0146
C8B	0.7737 (3)	0.5271 (2)	0.42418 (12)	0.0165
C9B	0.6463 (3)	0.60188 (19)	0.43630 (11)	0.0151
C10B	0.4808 (3)	0.59806 (19)	0.38219 (11)	0.0144
N11B	0.2930 (2)	0.49043 (16)	0.24801 (9)	0.0130
C12B	0.1523 (3)	0.55777 (19)	0.23644 (11)	0.0138
C13B	0.0312 (3)	0.40238 (18)	0.11173 (11)	0.0139
C14B	0.3049 (3)	0.39217 (19)	0.19191 (11)	0.0140
C15B	0.5689 (3)	0.43274 (19)	0.29911 (11)	0.0139
C16B	0.4478 (3)	0.51304 (19)	0.31342 (11)	0.0135
C17B	0.0111 (3)	0.50602 (19)	0.16292 (11)	0.0141
H1A	1.130 (2)	−0.1539 (13)	−0.2094 (9)	0.0204*
H2A	1.380 (2)	−0.0909 (13)	−0.1021 (9)	0.0206*
H3A	1.388 (2)	0.0793 (14)	−0.0051 (9)	0.0251*
H4A	1.142 (2)	0.1815 (13)	−0.0153 (9)	0.0215*
H5A	0.083 (2)	0.0145 (13)	−0.4368 (9)	0.0178*
H6A	0.541 (2)	−0.1385 (13)	−0.3938 (9)	0.0187*
H1B	−0.159 (2)	0.6286 (13)	0.1773 (9)	0.0204*
H2B	−0.388 (2)	0.5439 (14)	0.0634 (9)	0.0248*
H3B	−0.355 (2)	0.3688 (14)	−0.0209 (9)	0.0224*
H4B	−0.094 (2)	0.2847 (13)	0.0083 (9)	0.0208*
H5B	0.885 (2)	0.5353 (13)	0.4615 (9)	0.0195*
H6B	0.398 (2)	0.6491 (12)	0.3915 (9)	0.0160*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1A	0.0147 (2)	0.0165 (2)	0.0164 (2)	0.00768 (18)	0.00158 (17)	0.00171 (18)
Cl2A	0.0192 (2)	0.0251 (3)	0.0143 (2)	0.0077 (2)	−0.00299 (18)	−0.00561 (19)
O1A	0.0188 (7)	0.0163 (7)	0.0172 (7)	0.0078 (6)	0.0020 (6)	−0.0021 (6)
O2A	0.0182 (7)	0.0184 (7)	0.0177 (7)	0.0084 (6)	0.0001 (6)	−0.0036 (6)
C1A	0.0174 (10)	0.0143 (9)	0.0181 (10)	0.0060 (8)	0.0036 (8)	0.0031 (8)
C2A	0.0166 (10)	0.0196 (10)	0.0207 (10)	0.0089 (8)	0.0013 (8)	0.0042 (8)
C3A	0.0202 (10)	0.0255 (11)	0.0166 (10)	0.0097 (9)	−0.0037 (8)	0.0014 (8)
C4A	0.0196 (10)	0.0208 (10)	0.0138 (9)	0.0067 (8)	−0.0007 (8)	−0.0015 (8)
N5A	0.0154 (8)	0.0161 (8)	0.0138 (8)	0.0061 (7)	0.0005 (6)	0.0000 (6)
C6A	0.0131 (9)	0.0135 (9)	0.0146 (9)	0.0039 (7)	0.0020 (7)	0.0031 (7)
C7A	0.0137 (9)	0.0125 (9)	0.0154 (9)	0.0042 (7)	0.0033 (7)	0.0026 (7)
C8A	0.0122 (9)	0.0187 (10)	0.0144 (9)	0.0048 (8)	−0.0011 (7)	0.0024 (8)
C9A	0.0150 (9)	0.0151 (9)	0.0121 (9)	0.0016 (8)	0.0004 (7)	−0.0015 (7)
C10A	0.0134 (9)	0.0133 (9)	0.0162 (9)	0.0039 (7)	0.0012 (7)	−0.0005 (7)
N11A	0.0126 (8)	0.0131 (8)	0.0122 (8)	0.0038 (6)	−0.0005 (6)	−0.0011 (6)
C12A	0.0120 (9)	0.0138 (9)	0.0156 (9)	0.0025 (7)	0.0027 (7)	0.0024 (7)
C13A	0.0140 (9)	0.0137 (9)	0.0150 (9)	0.0043 (7)	0.0021 (7)	0.0030 (7)
C14A	0.0145 (9)	0.0116 (9)	0.0147 (9)	0.0046 (7)	0.0028 (7)	0.0010 (7)
C15A	0.0124 (9)	0.0121 (9)	0.0138 (9)	0.0028 (7)	0.0027 (7)	0.0024 (7)
C16A	0.0125 (9)	0.0145 (9)	0.0147 (9)	0.0033 (7)	0.0013 (7)	0.0027 (7)
C17A	0.0133 (9)	0.0130 (9)	0.0148 (9)	0.0034 (7)	0.0014 (7)	0.0028 (7)
Cl1B	0.0148 (2)	0.0186 (2)	0.0217 (2)	0.00967 (18)	0.00275 (18)	0.00399 (19)
Cl2B	0.0183 (2)	0.0231 (3)	0.0153 (2)	0.00847 (19)	−0.00197 (18)	−0.00346 (19)
O1B	0.0201 (7)	0.0182 (7)	0.0213 (7)	0.0103 (6)	0.0049 (6)	0.0004 (6)
O2B	0.0170 (7)	0.0174 (7)	0.0167 (7)	0.0085 (6)	−0.0007 (5)	−0.0024 (6)
C1B	0.0173 (9)	0.0151 (9)	0.0173 (9)	0.0070 (8)	0.0013 (8)	0.0010 (8)
C2B	0.0168 (10)	0.0214 (10)	0.0210 (10)	0.0097 (8)	−0.0012 (8)	0.0028 (8)
C3B	0.0179 (10)	0.0207 (10)	0.0162 (10)	0.0052 (8)	−0.0038 (8)	−0.0006 (8)
C4B	0.0207 (10)	0.0163 (9)	0.0157 (9)	0.0068 (8)	0.0010 (8)	−0.0003 (8)
N5B	0.0162 (8)	0.0149 (8)	0.0153 (8)	0.0059 (7)	0.0022 (6)	0.0011 (7)
C6B	0.0120 (9)	0.0157 (9)	0.0165 (9)	0.0035 (7)	0.0031 (7)	0.0038 (8)
C7B	0.0126 (9)	0.0141 (9)	0.0197 (10)	0.0065 (7)	0.0045 (7)	0.0048 (8)
C8B	0.0148 (9)	0.0190 (10)	0.0156 (9)	0.0057 (8)	−0.0010 (8)	0.0039 (8)
C9B	0.0160 (9)	0.0143 (9)	0.0128 (9)	0.0024 (7)	0.0013 (7)	−0.0001 (7)
C10B	0.0123 (9)	0.0158 (9)	0.0157 (9)	0.0055 (7)	0.0022 (7)	0.0009 (8)
N11B	0.0117 (7)	0.0142 (8)	0.0128 (8)	0.0048 (6)	0.0002 (6)	−0.0001 (6)
C12B	0.0120 (9)	0.0141 (9)	0.0155 (9)	0.0039 (7)	0.0022 (7)	0.0027 (7)
C13B	0.0145 (9)	0.0117 (9)	0.0158 (9)	0.0035 (7)	0.0030 (7)	0.0034 (7)
C14B	0.0141 (9)	0.0126 (9)	0.0166 (9)	0.0053 (7)	0.0049 (7)	0.0022 (7)
C15B	0.0124 (9)	0.0137 (9)	0.0162 (9)	0.0045 (7)	0.0034 (7)	0.0030 (7)
C16B	0.0106 (8)	0.0144 (9)	0.0152 (9)	0.0034 (7)	0.0009 (7)	0.0029 (7)
C17B	0.0145 (9)	0.0137 (9)	0.0144 (9)	0.0045 (7)	0.0024 (7)	0.0034 (7)

Geometric parameters (Å, º) top

Cl1A—C7A	1.7272 (19)	C1A—C2A	1.379 (3)
Cl2A—C9A	1.7358 (19)	C1A—H1A	0.937 (15)
Cl1B—C7B	1.7276 (19)	C2A—C3A	1.399 (3)
Cl2B—C9B	1.734 (2)	C2A—H2A	0.929 (16)
O1A—C6A	1.213 (2)	C3A—C4A	1.379 (3)
O2A—C12A	1.221 (2)	C3A—H3A	0.937 (16)
O1B—C6B	1.211 (2)	C4A—C13A	1.399 (3)
O2B—C12B	1.221 (2)	C4A—H4A	0.937 (15)
N5A—C13A	1.405 (2)	C14A—C6A	1.518 (3)
N5A—C14A	1.275 (2)	C15B—C7B	1.387 (3)
N11A—C16A	1.419 (2)	C15B—C16B	1.405 (3)
N11A—C12A	1.396 (2)	C15B—C6B	1.480 (3)
N11A—C14A	1.395 (2)	C7B—C8B	1.387 (3)
N5B—C13B	1.401 (2)	C8B—C9B	1.389 (3)
N5B—C14B	1.277 (3)	C8B—H5B	0.931 (15)
N11B—C16B	1.421 (2)	C9B—C10B	1.390 (3)
N11B—C12B	1.394 (2)	C10B—C16B	1.384 (3)
N11B—C14B	1.396 (2)	C10B—H6B	0.930 (15)
C15A—C7A	1.386 (3)	C12B—C17B	1.467 (3)
C15A—C16A	1.401 (3)	C17B—C1B	1.399 (3)
C15A—C6A	1.477 (3)	C17B—C13B	1.410 (3)
C7A—C8A	1.389 (3)	C1B—C2B	1.378 (3)
C8A—C9A	1.389 (3)	C1B—H1B	0.942 (15)
C8A—H5A	0.925 (15)	C2B—C3B	1.402 (3)
C9A—C10A	1.390 (3)	C2B—H2B	0.947 (16)
C10A—C16A	1.380 (3)	C3B—C4B	1.377 (3)
C10A—H6A	0.938 (15)	C3B—H3B	0.937 (16)
C12A—C17A	1.465 (3)	C4B—C13B	1.399 (3)
C17A—C1A	1.397 (3)	C4B—H4B	0.936 (16)
C17A—C13A	1.412 (3)	C14B—C6B	1.517 (3)

Cl1A—C7A—C15A	121.65 (15)	Cl1B—C7B—C15B	121.43 (15)
Cl1A—C7A—C8A	118.05 (15)	Cl1B—C7B—C8B	118.59 (15)
C15A—C7A—C8A	120.30 (18)	C15B—C7B—C8B	119.98 (18)
C7A—C15A—C6A	132.59 (18)	C7B—C15B—C6B	132.47 (18)
C7A—C15A—C16A	118.79 (17)	C7B—C15B—C16B	118.96 (18)
C6A—C15A—C16A	108.62 (16)	C6B—C15B—C16B	108.54 (16)
C15A—C6A—O1A	129.87 (18)	C15B—C6B—O1B	130.04 (18)
C15A—C6A—C14A	104.37 (15)	C15B—C6B—C14B	104.47 (16)
O1A—C6A—C14A	125.75 (17)	O1B—C6B—C14B	125.46 (18)
C6A—C14A—N5A	126.26 (17)	C6B—C14B—N11B	107.35 (16)
C6A—C14A—N11A	107.38 (16)	C6B—C14B—N5B	126.40 (17)
N5A—C14A—N11A	126.35 (17)	N11B—C14B—N5B	126.25 (17)
C14A—N5A—C13A	115.81 (17)	C14B—N11B—C16B	110.20 (15)
N5A—C13A—C4A	118.48 (17)	C14B—N11B—C12B	122.59 (16)
N5A—C13A—C17A	122.13 (17)	C16B—N11B—C12B	127.14 (16)
C4A—C13A—C17A	119.38 (18)	N11B—C16B—C15B	109.35 (16)
C13A—C4A—C3A	119.69 (19)	N11B—C16B—C10B	127.71 (17)
C13A—C4A—H4A	120.2 (10)	C15B—C16B—C10B	122.94 (18)
C3A—C4A—H4A	120.2 (10)	C16B—C10B—C9B	115.54 (18)
C4A—C3A—C2A	120.96 (19)	C16B—C10B—H6B	122.2 (10)
C4A—C3A—H3A	119.0 (10)	C9B—C10B—H6B	122.3 (10)
C2A—C3A—H3A	120.0 (10)	C10B—C9B—C8B	123.79 (18)
C3A—C2A—C1A	120.04 (19)	C10B—C9B—Cl2B	119.12 (15)
C3A—C2A—H2A	121.2 (10)	C8B—C9B—Cl2B	117.08 (15)
C1A—C2A—H2A	118.8 (10)	C9B—C8B—C7B	118.75 (18)
C2A—C1A—C17A	119.86 (19)	C9B—C8B—H5B	120.6 (10)
C2A—C1A—H1A	119.9 (10)	C7B—C8B—H5B	120.6 (10)
C17A—C1A—H1A	120.2 (10)	N11B—C12B—O2B	121.91 (17)
C13A—C17A—C1A	120.07 (18)	N11B—C12B—C17B	112.41 (16)
C13A—C17A—C12A	120.66 (17)	O2B—C12B—C17B	125.68 (17)
C1A—C17A—C12A	119.26 (17)	C12B—C17B—C13B	120.36 (17)
C17A—C12A—N11A	112.36 (16)	C12B—C17B—C1B	119.93 (17)
C17A—C12A—O2A	125.53 (18)	C13B—C17B—C1B	119.70 (18)
N11A—C12A—O2A	122.11 (17)	C17B—C13B—N5B	122.53 (17)
C12A—N11A—C14A	122.65 (16)	C17B—C13B—C4B	119.38 (18)
C12A—N11A—C16A	127.27 (16)	N5B—C13B—C4B	118.09 (17)
C14A—N11A—C16A	110.08 (15)	C13B—N5B—C14B	115.64 (16)
N11A—C16A—C15A	109.50 (16)	C13B—C4B—C3B	120.22 (19)
N11A—C16A—C10A	127.57 (18)	C13B—C4B—H4B	119.5 (10)
C15A—C16A—C10A	122.93 (18)	C3B—C4B—H4B	120.2 (10)
C16A—C10A—C9A	115.95 (18)	C4B—C3B—C2B	120.39 (19)
C16A—C10A—H6A	122.5 (10)	C4B—C3B—H3B	118.8 (10)
C9A—C10A—H6A	121.5 (10)	C2B—C3B—H3B	120.8 (10)
C10A—C9A—C8A	123.45 (18)	C3B—C2B—C1B	120.12 (19)
C10A—C9A—Cl2A	118.47 (15)	C3B—C2B—H2B	120.2 (10)
C8A—C9A—Cl2A	118.07 (15)	C1B—C2B—H2B	119.6 (10)
C9A—C8A—C7A	118.51 (17)	C17B—C1B—C2B	120.18 (18)
C9A—C8A—H5A	120.8 (10)	C17B—C1B—H1B	120.2 (10)
C7A—C8A—H5A	120.6 (10)	C2B—C1B—H1B	119.6 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1B—H1B···Cl1Aⁱ	0.94 (2)	2.73 (2)	3.637 (2)	162 (1)
C2A—H2A···O1Bⁱⁱ	0.93 (2)	2.54 (2)	3.264 (3)	135 (1)
C4B—H4B···N5Aⁱⁱⁱ	0.94 (2)	2.56 (2)	3.422 (3)	154 (1)
C10A—H6A···Cl2B^iv	0.94 (2)	2.67 (2)	3.585 (2)	165 (1)

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+2, −y, −z; (iii) x−1, y, z; (iv) x, y−1, z−1.

Experimental details

Crystal data
Chemical formula	C₁₅H₆Cl₂N₂O₂
M_r	317.13
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.0179 (2), 10.7276 (3), 17.2338 (12)
α, β, γ (°)	94.908 (7), 96.709 (7), 107.395 (8)
V (Å³)	1219.66 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.54
Crystal size (mm)	0.54 × 0.48 × 0.35

Data collection
Diffractometer	Rigaku R-AXIS RAPID-II imaging plate
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.633, 0.899
No. of measured, independent and observed [I > 2σ(I)] reflections	31502, 5585, 4830
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.082, 1.00
No. of reflections	5571
No. of parameters	416
No. of restraints	84
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.36

Computer programs: CrystalClear (Rigaku Americas, 2009), HKL-2000 (Otwinowski & Minor, 1997), SHELXS86 (Sheldrick, 2008), CRYSTALS (Betteridge et al., 2003), CAMERON (Watkin et al., 1996).

Selected bond lengths (Å) top

Cl1A—C7A	1.7272 (19)	N5A—C14A	1.275 (2)
Cl2A—C9A	1.7358 (19)	N11A—C16A	1.419 (2)
Cl1B—C7B	1.7276 (19)	N11A—C12A	1.396 (2)
Cl2B—C9B	1.734 (2)	N11A—C14A	1.395 (2)
O1A—C6A	1.213 (2)	N5B—C13B	1.401 (2)
O2A—C12A	1.221 (2)	N5B—C14B	1.277 (3)
O1B—C6B	1.211 (2)	N11B—C16B	1.421 (2)
O2B—C12B	1.221 (2)	N11B—C12B	1.394 (2)
N5A—C13A	1.405 (2)	N11B—C14B	1.396 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1B—H1B···Cl1Aⁱ	0.942 (15)	2.729 (15)	3.637 (2)	162.0 (12)
C2A—H2A···O1Bⁱⁱ	0.929 (16)	2.539 (15)	3.264 (3)	134.9 (12)
C4B—H4B···N5Aⁱⁱⁱ	0.936 (16)	2.556 (15)	3.422 (3)	153.9 (12)
C10A—H6A···Cl2B^iv	0.938 (15)	2.673 (15)	3.585 (2)	164.8 (12)

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+2, −y, −z; (iii) x−1, y, z; (iv) x, y−1, z−1.

Acknowledgements

This study was supported by Stanley Medical Research Institute (grant 08R-2032) and the NSF (grant CHE-0922366 for X-ray diffractometer).

References

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