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The title compound, C21H15ClN4O2, is a close analogue of one of the most potent anti­mycobacterial purines, namely 2-chloro-6-(2-fur­yl)-9-[(4-methoxy­phen­yl)meth­yl]-9H-purine. Dimers are stabilized by π–π stacking and C—H...π inter­actions. Inter­molecular C—H...O hydrogen bonding between the CH group of the purine ring and the O atom in the benzofuran ring, and also π–π stacking in another direction, that result in an average interplanar distance of 3.339 Å between the pyrimidine ring (or 3.424 Å with imidazole ring) and the benzene ring in the benzofuryl group, and 3.318 Å between the furyl ring and the imidazole ring, building a three-dimensional supra­molecular network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022647/xu2252sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022647/xu2252Isup2.hkl
Contains datablock I

CCDC reference: 651527

Key indicators

  • Single-crystal X-ray study
  • T = 112 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.036
  • wR factor = 0.094
  • Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.642 0.952 Tmin(prime) and Tmax expected: 0.928 0.952 RR(prime) = 0.692 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.69
Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H8 .. O18 .. 2.66 Ang.
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

We have discovered that certain 6-aryl-9-benzylpurines are potent antimycobacterials in vitro and may have a potensial as antitubercular drugs (Bakkestuen et al., 2000; Gundersen et al., 2002; Bakkestuen et al., 2005; Braendvang & Gundersen, 2005). The title compound, (I), was synthesized as a close analog of the previously reported antimycobacterial 2-chloro-6-(2-furanyl)-9-[(4-methoxyphenyl)methyl]-9H-purine, (II), (Bakkestuen et al., 2005).

The molecular geometries is illustrated in Fig. 1. The selected bond lenghts and angles are listed in Table 1 and compared with the recently reported X-ray structure of compound (II) (Braendvang & Gundersen, 2007a). There are only small differences in bond lenghts and angles in these two compounds, specially molecule A in compound (II) resembles the title compound (I) (Table 1). In compound (I) the angle between the mean plane of the purine ring system and the furyl ring C17/O18/C19—C21 is 4.49 (7)°, or 4.82 (5)° if the mean plane of benzofuryl is used. In compound (II) the angles were 2.31 (6)° in molecule A and 2.79 (5)° in molecule B.

The positions of the benzyl groups are only slightly different in compound (I) and (II) as seen from the torsion angles C4—N9—C10—C11 and N9—C10—C11—C12 (Table 1). The benzene ring C11—C16 is inclined at an angle of 70.68 (6)° to the purine ring in compound (I). Previously reported for compound (II) is 73.64 (5)° in molecule A and 77.80 (4)° in molecule B.

Fig. 2 shows the crystal packing of (I) in the unit cell. The conformation adopted by the benzene rings allows for simultaneous C—H···π interactions, and ππ interactions to form dimers of molecules (Fig. 3). The C—H···π interactions occurs between the C26—H26···Cg1i (Table 2) (Cg1 is the centroid of the benzene ring C11—C16) [symmetry code: (i) 2 - x, 1 - y, 1 - z]. In these dimers, ππ interactions occurs between the purine ring system and the benzene ring C19/C20/C24—C27 in the benzofuryl group. In this interaction the benzene ring C19/C20/C24—C27 and the pyrimidine ring N1/C2/N3/C4—C6 are slipped by 18.7 ° relative to their ring perpendiculars (the average interplanar distance between the benzene ring in the benzofuryl group and the pyrimidine ring N1/C2/N3/C4—C6 is 3.339 Å), the ring-centroid to ring-centroid distance being 3.5277 (10) Å. The average interplanar distance between the benzene ring in the benzofuryl group and the imidazole ring C4/C5/N7/C8/N9 is 3.424 Å (the two rings are slipped by 22.8° relative to their ring perpendiculars), the ring-centroid to ring-centroid distance being 3.7161 (10) Å.

The crystal packing (Fig. 2) gives further ππ interactions between the imidazole ring (C4A—N9A) and the furyl ring C17/O18/C19—C21iii, the ring-centroid to centroid distance is 3.5084 (10) Å [symmetry code: (iii) 1 - x, 1 - y, 1 - z]. In this interaction the average interplanar distance is 3.318 Å and the two rings are slipped by 19.0° relative to their ring perpendiculars.

Finally, the orientation of the furyl group in compound (I) is stabilized by weak C8—H8···O18ii hydrogen bonding, forming infinite chains of molecules (Table 2 and Fig. 3) [symmetry code: (ii) x - 1, y, z - 1].

The molecular packing of compound (I) in overall is very similar to the previous reported (II) (Braendvang & Gundersen, 2007a).

Related literature top

Bond lengths and angles in the title compound, (I), are in good agreement with those found for 6-furyl- and 6-thienyl-9-benzyl-purines (Braendvang & Gundersen, 2007a; Mazumdar et al., 2001), and also with the recently reported non-purine analog 4-(2-furyl)-1-[(4-methoxyphenyl)methyl]-1H-pyrazolo[3,4–d]pyrimidine (Braendvang & Gundersen, 2007b). The molecular packing as well as the orientation of the furyl ring and benzene ring very much resemble the recently reported analog 2-chloro-6-(2-furanyl)-9-[(4-methoxyphenyl)methyl]-9H-purine, (II) (Braendvang & Gundersen, 2007a).

For related literature, see: Bakkestuen et al. (2000, 2005); Braendvang & Gundersen (2005); Gundersen et al. (2002); Liebeskind & Wang (1993).

Experimental top

The title compound was synthesized by regioselective Stille coupling using benzofur-2-yl stannane as described for compound (II) (Bakkestuen et al., 2005). The benzofur-2-yl stannane used was made by literature procedure (Liebeskind & Wang, 1993). Crystals suitable for X-ray diffraction studies were obtained from a solution of title compound (27 mg) in CH2Cl2 (0.8 ml) with a top layer of heptane (0.8 ml).

Refinement top

H atoms were positioned geometrically and allowed to ride and rotate (for the CH3 group) on their carrier atoms, with C—H = 0.95 (aromatic), 0.99 (CH2) or 0.98 Å (CH3) and with Uiso(H) = 1.2Ueq(C) for CH2 and aromatic, or 1.5Ueq(C) for CH3.

Structure description top

We have discovered that certain 6-aryl-9-benzylpurines are potent antimycobacterials in vitro and may have a potensial as antitubercular drugs (Bakkestuen et al., 2000; Gundersen et al., 2002; Bakkestuen et al., 2005; Braendvang & Gundersen, 2005). The title compound, (I), was synthesized as a close analog of the previously reported antimycobacterial 2-chloro-6-(2-furanyl)-9-[(4-methoxyphenyl)methyl]-9H-purine, (II), (Bakkestuen et al., 2005).

The molecular geometries is illustrated in Fig. 1. The selected bond lenghts and angles are listed in Table 1 and compared with the recently reported X-ray structure of compound (II) (Braendvang & Gundersen, 2007a). There are only small differences in bond lenghts and angles in these two compounds, specially molecule A in compound (II) resembles the title compound (I) (Table 1). In compound (I) the angle between the mean plane of the purine ring system and the furyl ring C17/O18/C19—C21 is 4.49 (7)°, or 4.82 (5)° if the mean plane of benzofuryl is used. In compound (II) the angles were 2.31 (6)° in molecule A and 2.79 (5)° in molecule B.

The positions of the benzyl groups are only slightly different in compound (I) and (II) as seen from the torsion angles C4—N9—C10—C11 and N9—C10—C11—C12 (Table 1). The benzene ring C11—C16 is inclined at an angle of 70.68 (6)° to the purine ring in compound (I). Previously reported for compound (II) is 73.64 (5)° in molecule A and 77.80 (4)° in molecule B.

Fig. 2 shows the crystal packing of (I) in the unit cell. The conformation adopted by the benzene rings allows for simultaneous C—H···π interactions, and ππ interactions to form dimers of molecules (Fig. 3). The C—H···π interactions occurs between the C26—H26···Cg1i (Table 2) (Cg1 is the centroid of the benzene ring C11—C16) [symmetry code: (i) 2 - x, 1 - y, 1 - z]. In these dimers, ππ interactions occurs between the purine ring system and the benzene ring C19/C20/C24—C27 in the benzofuryl group. In this interaction the benzene ring C19/C20/C24—C27 and the pyrimidine ring N1/C2/N3/C4—C6 are slipped by 18.7 ° relative to their ring perpendiculars (the average interplanar distance between the benzene ring in the benzofuryl group and the pyrimidine ring N1/C2/N3/C4—C6 is 3.339 Å), the ring-centroid to ring-centroid distance being 3.5277 (10) Å. The average interplanar distance between the benzene ring in the benzofuryl group and the imidazole ring C4/C5/N7/C8/N9 is 3.424 Å (the two rings are slipped by 22.8° relative to their ring perpendiculars), the ring-centroid to ring-centroid distance being 3.7161 (10) Å.

The crystal packing (Fig. 2) gives further ππ interactions between the imidazole ring (C4A—N9A) and the furyl ring C17/O18/C19—C21iii, the ring-centroid to centroid distance is 3.5084 (10) Å [symmetry code: (iii) 1 - x, 1 - y, 1 - z]. In this interaction the average interplanar distance is 3.318 Å and the two rings are slipped by 19.0° relative to their ring perpendiculars.

Finally, the orientation of the furyl group in compound (I) is stabilized by weak C8—H8···O18ii hydrogen bonding, forming infinite chains of molecules (Table 2 and Fig. 3) [symmetry code: (ii) x - 1, y, z - 1].

The molecular packing of compound (I) in overall is very similar to the previous reported (II) (Braendvang & Gundersen, 2007a).

Bond lengths and angles in the title compound, (I), are in good agreement with those found for 6-furyl- and 6-thienyl-9-benzyl-purines (Braendvang & Gundersen, 2007a; Mazumdar et al., 2001), and also with the recently reported non-purine analog 4-(2-furyl)-1-[(4-methoxyphenyl)methyl]-1H-pyrazolo[3,4–d]pyrimidine (Braendvang & Gundersen, 2007b). The molecular packing as well as the orientation of the furyl ring and benzene ring very much resemble the recently reported analog 2-chloro-6-(2-furanyl)-9-[(4-methoxyphenyl)methyl]-9H-purine, (II) (Braendvang & Gundersen, 2007a).

For related literature, see: Bakkestuen et al. (2000, 2005); Braendvang & Gundersen (2005); Gundersen et al. (2002); Liebeskind & Wang (1993).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Version 1.08; Farrugia, 1997) and POV-RAY for Windows (Persistence of Vision Pty Ltd, 2004); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The packing of (I) in the unit cell. H atoms have been omitted for clarity.
[Figure 3] Fig. 3. A partial packing view, showing the intermolecular C—H···π interactions (dashed lines labelled π) between the C26—H26 and the benzyl group (C11—C16) in compound (I). Dashed lines labelled with an asterisk (*) are the intermolecular C8—H8···O18 hydrogen bonding. H atoms not involved in hydrogen-bonding interactions have been omitted for clarity. [symmetry code: (i) 2 - x, 1 - y, 1 - z; (ii) x - 1, y, z - 1; (iii) 1 - x, 1 - y, -z].
[Figure 4] Fig. 4. The structures of (I) and (II).
6-(2-Benzofuryl)-2-chloro-9-[(4-methoxyphenyl)methyl]-9H-purine top
Crystal data top
C21H15ClN4O2F(000) = 808
Mr = 390.82Dx = 1.476 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7413 reflections
a = 8.0721 (8) Åθ = 2.8–28.9°
b = 28.668 (3) ŵ = 0.24 mm1
c = 8.3764 (9) ÅT = 112 K
β = 114.876 (2)°Block, colourless
V = 1758.6 (3) Å30.3 × 0.2 × 0.2 mm
Z = 4
Data collection top
Siemens SMART CCD
diffractometer
3366 reflections with I > 2σ(I)
Sets of exposures each taken over 0.3° ω rotation scansRint = 0.044
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
θmax = 29.1°, θmin = 1.4°
Tmin = 0.642, Tmax = 0.952h = 1010
16890 measured reflectionsk = 3839
4334 independent reflectionsl = 1011
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0518P)2 + 0.2117P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.036(Δ/σ)max = 0.001
wR(F2) = 0.094Δρmax = 0.31 e Å3
S = 1.03Δρmin = 0.23 e Å3
4334 reflectionsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
255 parametersExtinction coefficient: 0.0045 (10)
0 restraints
Crystal data top
C21H15ClN4O2V = 1758.6 (3) Å3
Mr = 390.82Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.0721 (8) ŵ = 0.24 mm1
b = 28.668 (3) ÅT = 112 K
c = 8.3764 (9) Å0.3 × 0.2 × 0.2 mm
β = 114.876 (2)°
Data collection top
Siemens SMART CCD
diffractometer
4334 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3366 reflections with I > 2σ(I)
Tmin = 0.642, Tmax = 0.952Rint = 0.044
16890 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.094H-atom parameters constrained
S = 1.03Δρmax = 0.31 e Å3
4334 reflectionsΔρmin = 0.23 e Å3
255 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C230.4460 (2)0.75117 (6)0.4061 (2)0.0304 (3)
H23C0.49440.77790.44570.046*
H23B0.31290.75010.47190.046*
H23A0.49940.72240.42660.046*
C140.42248 (18)0.72315 (5)0.14688 (19)0.0219 (3)
C150.33819 (19)0.68194 (5)0.22890 (18)0.0220 (3)
H150.3260.67470.3440.026*
C160.27211 (19)0.65160 (5)0.14000 (18)0.0224 (3)
H160.2130.62370.19640.027*
C110.29012 (18)0.66101 (5)0.02899 (18)0.0206 (3)
C120.3764 (2)0.70225 (5)0.1092 (2)0.0256 (3)
H120.39070.70920.22510.031*
C130.4416 (2)0.73323 (5)0.0223 (2)0.0270 (3)
H130.49930.76130.07820.032*
C100.21757 (19)0.62721 (5)0.1228 (2)0.0251 (3)
H10B0.18990.64440.21110.03*
H10A0.10220.61340.03640.03*
C80.3488 (2)0.54524 (5)0.14963 (19)0.0248 (3)
H80.25880.53460.040.03*
C50.58017 (18)0.54779 (4)0.39524 (17)0.0190 (3)
C60.73824 (18)0.54209 (4)0.55173 (17)0.0182 (3)
C20.70456 (19)0.61808 (5)0.61788 (18)0.0198 (3)
C40.49637 (18)0.59170 (5)0.36956 (18)0.0192 (3)
C170.84136 (18)0.49884 (4)0.59799 (18)0.0185 (3)
C210.82115 (18)0.45845 (4)0.50752 (18)0.0201 (3)
H210.72930.45160.39370.024*
C200.96580 (18)0.42808 (5)0.61741 (18)0.0192 (3)
C241.02383 (19)0.38258 (5)0.60394 (19)0.0223 (3)
H240.96070.36440.50130.027*
C251.1748 (2)0.36497 (5)0.74343 (19)0.0240 (3)
H251.21620.33440.73570.029*
C261.2679 (2)0.39127 (5)0.8958 (2)0.0246 (3)
H261.37080.3780.98970.03*
C271.2137 (2)0.43633 (5)0.91346 (19)0.0244 (3)
H271.27630.45431.01680.029*
C191.06353 (18)0.45333 (4)0.77165 (18)0.0199 (3)
N90.34760 (15)0.58943 (4)0.21140 (15)0.0211 (3)
N70.48406 (16)0.51863 (4)0.25380 (15)0.0235 (3)
N10.80044 (15)0.57858 (4)0.66414 (15)0.0194 (2)
N30.55232 (16)0.62840 (4)0.47883 (15)0.0204 (2)
O220.49164 (14)0.75576 (3)0.22214 (14)0.0290 (2)
O180.98871 (13)0.49710 (3)0.76115 (12)0.0209 (2)
Cl20.79826 (5)0.664269 (11)0.76375 (5)0.02636 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C230.0249 (8)0.0330 (8)0.0319 (8)0.0020 (6)0.0106 (7)0.0137 (7)
C140.0175 (7)0.0184 (6)0.0280 (7)0.0015 (5)0.0078 (6)0.0063 (5)
C150.0217 (7)0.0208 (7)0.0216 (7)0.0009 (5)0.0071 (6)0.0026 (5)
C160.0201 (7)0.0171 (6)0.0253 (7)0.0006 (5)0.0049 (6)0.0029 (5)
C110.0151 (6)0.0217 (7)0.0230 (7)0.0038 (5)0.0061 (5)0.0069 (5)
C120.0252 (8)0.0272 (7)0.0242 (7)0.0012 (6)0.0101 (6)0.0005 (6)
C130.0277 (8)0.0196 (7)0.0313 (8)0.0036 (6)0.0100 (7)0.0031 (6)
C100.0174 (7)0.0273 (7)0.0278 (8)0.0036 (6)0.0066 (6)0.0109 (6)
C80.0247 (7)0.0228 (7)0.0230 (7)0.0054 (6)0.0063 (6)0.0021 (5)
C50.0196 (7)0.0170 (6)0.0214 (7)0.0017 (5)0.0096 (6)0.0031 (5)
C60.0185 (7)0.0173 (6)0.0202 (7)0.0005 (5)0.0094 (6)0.0027 (5)
C20.0209 (7)0.0185 (6)0.0215 (7)0.0005 (5)0.0104 (6)0.0011 (5)
C40.0169 (6)0.0203 (6)0.0211 (7)0.0002 (5)0.0087 (6)0.0052 (5)
C170.0170 (6)0.0186 (6)0.0192 (7)0.0011 (5)0.0069 (5)0.0032 (5)
C210.0194 (7)0.0194 (6)0.0203 (7)0.0012 (5)0.0072 (6)0.0017 (5)
C200.0192 (7)0.0172 (6)0.0224 (7)0.0013 (5)0.0099 (6)0.0017 (5)
C240.0234 (7)0.0181 (6)0.0276 (7)0.0025 (5)0.0128 (6)0.0012 (5)
C250.0255 (8)0.0163 (6)0.0352 (8)0.0025 (5)0.0178 (7)0.0039 (6)
C260.0213 (7)0.0236 (7)0.0287 (8)0.0047 (5)0.0103 (6)0.0079 (6)
C270.0248 (7)0.0218 (7)0.0239 (7)0.0011 (6)0.0077 (6)0.0015 (6)
C190.0216 (7)0.0153 (6)0.0253 (7)0.0010 (5)0.0123 (6)0.0029 (5)
N90.0184 (6)0.0206 (6)0.0218 (6)0.0006 (4)0.0061 (5)0.0051 (4)
N70.0238 (6)0.0197 (6)0.0230 (6)0.0033 (5)0.0058 (5)0.0020 (5)
N10.0200 (6)0.0178 (5)0.0215 (6)0.0013 (4)0.0097 (5)0.0019 (4)
N30.0204 (6)0.0189 (6)0.0224 (6)0.0015 (4)0.0094 (5)0.0026 (4)
O220.0292 (6)0.0234 (5)0.0328 (6)0.0054 (4)0.0115 (5)0.0074 (4)
O180.0216 (5)0.0161 (5)0.0214 (5)0.0033 (4)0.0053 (4)0.0015 (4)
Cl20.0269 (2)0.01996 (17)0.02673 (19)0.00263 (13)0.00591 (15)0.00372 (13)
Geometric parameters (Å, º) top
C23—O221.4318 (19)C5—C61.4022 (19)
C23—H23C0.98C6—N11.3548 (17)
C23—H23B0.98C6—C171.4521 (18)
C23—H23A0.98C2—N31.3229 (18)
C14—O221.3708 (16)C2—N11.3338 (17)
C14—C131.390 (2)C2—Cl21.7439 (14)
C14—C151.3918 (19)C4—N31.3420 (17)
C15—C161.3892 (19)C4—N91.3650 (18)
C15—H150.95C17—C211.3556 (19)
C16—C111.387 (2)C17—O181.3847 (16)
C16—H160.95C21—C201.4368 (18)
C11—C121.393 (2)C21—H210.95
C11—C101.5122 (19)C20—C191.3994 (19)
C12—C131.385 (2)C20—C241.4064 (19)
C12—H120.95C24—C251.381 (2)
C13—H130.95C24—H240.95
C10—N91.4732 (17)C25—C261.398 (2)
C10—H10B0.99C25—H250.95
C10—H10A0.99C26—C271.3914 (19)
C8—N71.3169 (18)C26—H260.95
C8—N91.3699 (18)C27—C191.3810 (19)
C8—H80.95C27—H270.95
C5—N71.3896 (18)C19—O181.3790 (15)
C5—C41.4021 (18)
O22—C23—H23C109.5N3—C2—N1131.02 (13)
O22—C23—H23B109.5N3—C2—Cl2114.55 (10)
H23C—C23—H23B109.5N1—C2—Cl2114.42 (10)
O22—C23—H23A109.5N3—C4—N9127.27 (12)
H23C—C23—H23A109.5N3—C4—C5126.66 (12)
H23B—C23—H23A109.5N9—C4—C5106.07 (12)
O22—C14—C13115.79 (12)C21—C17—O18111.86 (11)
O22—C14—C15124.13 (13)C21—C17—C6131.26 (13)
C13—C14—C15120.09 (13)O18—C17—C6116.88 (11)
C16—C15—C14119.02 (13)C17—C21—C20106.57 (12)
C16—C15—H15120.5C17—C21—H21126.7
C14—C15—H15120.5C20—C21—H21126.7
C11—C16—C15121.73 (13)C19—C20—C24118.46 (12)
C11—C16—H16119.1C19—C20—C21105.57 (11)
C15—C16—H16119.1C24—C20—C21135.97 (13)
C16—C11—C12118.28 (13)C25—C24—C20118.44 (13)
C16—C11—C10120.54 (13)C25—C24—H24120.8
C12—C11—C10121.17 (13)C20—C24—H24120.8
C13—C12—C11120.94 (14)C24—C25—C26121.29 (13)
C13—C12—H12119.5C24—C25—H25119.4
C11—C12—H12119.5C26—C25—H25119.4
C12—C13—C14119.92 (13)C27—C26—C25121.69 (13)
C12—C13—H13120C27—C26—H26119.2
C14—C13—H13120C25—C26—H26119.2
N9—C10—C11112.54 (11)C19—C27—C26115.96 (13)
N9—C10—H10B109.1C19—C27—H27122
C11—C10—H10B109.1C26—C27—H27122
N9—C10—H10A109.1O18—C19—C27125.35 (12)
C11—C10—H10A109.1O18—C19—C20110.50 (11)
H10B—C10—H10A107.8C27—C19—C20124.15 (12)
N7—C8—N9114.90 (13)C4—N9—C8105.52 (11)
N7—C8—H8122.6C4—N9—C10127.12 (12)
N9—C8—H8122.6C8—N9—C10127.32 (12)
N7—C5—C4110.43 (12)C8—N7—C5103.09 (11)
N7—C5—C6133.55 (12)C2—N1—C6116.97 (12)
C4—C5—C6116.02 (12)C2—N3—C4110.28 (11)
N1—C6—C5119.02 (12)C14—O22—C23117.51 (11)
N1—C6—C17118.07 (12)C19—O18—C17105.49 (10)
C5—C6—C17122.90 (12)
O22—C14—C15—C16179.57 (13)C25—C26—C27—C190.2 (2)
C13—C14—C15—C160.7 (2)C26—C27—C19—O18179.33 (13)
C14—C15—C16—C110.9 (2)C26—C27—C19—C200.7 (2)
C15—C16—C11—C120.3 (2)C24—C20—C19—O18179.47 (12)
C15—C16—C11—C10179.72 (13)C21—C20—C19—O180.71 (15)
C16—C11—C12—C130.4 (2)C24—C20—C19—C270.5 (2)
C10—C11—C12—C13179.60 (13)C21—C20—C19—C27179.31 (13)
C11—C12—C13—C140.5 (2)N3—C4—N9—C8179.55 (13)
O22—C14—C13—C12179.79 (13)C5—C4—N9—C80.27 (14)
C15—C14—C13—C120.1 (2)N3—C4—N9—C101.8 (2)
C16—C11—C10—N984.43 (16)C5—C4—N9—C10178.07 (12)
C12—C11—C10—N995.59 (16)N7—C8—N9—C40.36 (16)
N7—C5—C6—N1178.71 (13)N7—C8—N9—C10178.16 (12)
C4—C5—C6—N11.07 (18)C11—C10—N9—C479.64 (17)
N7—C5—C6—C170.1 (2)C11—C10—N9—C897.70 (16)
C4—C5—C6—C17179.86 (12)N9—C8—N7—C50.28 (16)
N7—C5—C4—N3179.71 (12)C4—C5—N7—C80.10 (15)
C6—C5—C4—N30.1 (2)C6—C5—N7—C8179.70 (14)
N7—C5—C4—N90.11 (15)N3—C2—N1—C61.5 (2)
C6—C5—C4—N9179.95 (11)Cl2—C2—N1—C6177.23 (9)
N1—C6—C17—C21174.32 (14)C5—C6—N1—C20.43 (18)
C5—C6—C17—C214.5 (2)C17—C6—N1—C2179.28 (12)
N1—C6—C17—O184.85 (17)N1—C2—N3—C42.3 (2)
C5—C6—C17—O18176.35 (11)Cl2—C2—N3—C4176.42 (9)
O18—C17—C21—C200.57 (15)N9—C4—N3—C2178.44 (13)
C6—C17—C21—C20178.64 (13)C5—C4—N3—C21.34 (19)
C17—C21—C20—C190.76 (15)C13—C14—O22—C23168.83 (13)
C17—C21—C20—C24179.47 (15)C15—C14—O22—C2311.5 (2)
C19—C20—C24—C250.12 (19)C27—C19—O18—C17179.64 (13)
C21—C20—C24—C25179.87 (14)C20—C19—O18—C170.38 (14)
C20—C24—C25—C260.6 (2)C21—C17—O18—C190.13 (14)
C24—C25—C26—C270.4 (2)C6—C17—O18—C19179.20 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C26—H26···Cg1i0.952.853.6453 (18)141
C8—H8···O18ii0.952.663.6034 (17)172
Symmetry codes: (i) x+2, y+1, z+1; (ii) x1, y, z1.

Experimental details

Crystal data
Chemical formulaC21H15ClN4O2
Mr390.82
Crystal system, space groupMonoclinic, P21/n
Temperature (K)112
a, b, c (Å)8.0721 (8), 28.668 (3), 8.3764 (9)
β (°) 114.876 (2)
V3)1758.6 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.3 × 0.2 × 0.2
Data collection
DiffractometerSiemens SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.642, 0.952
No. of measured, independent and
observed [I > 2σ(I)] reflections
16890, 4334, 3366
Rint0.044
(sin θ/λ)max1)0.685
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.094, 1.03
No. of reflections4334
No. of parameters255
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.23

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Version 1.08; Farrugia, 1997) and POV-RAY for Windows (Persistence of Vision Pty Ltd, 2004), SHELXL97 and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C26—H26···Cg1i0.952.853.6453 (18)141
C8—H8···O18ii0.952.663.6034 (17)172
Symmetry codes: (i) x+2, y+1, z+1; (ii) x1, y, z1.
Table 1. A comparison of selected geometric parameters (Å, °) of (I) and molecules A and B in (II) top
Compound (I)Molecule A in (II)aMolecule B in (II)a
C6—C171.4521 (18)1.4479 (15)1.4497 (15)
C10—N91.4732 (17)1.4755 (15)1.4740 (15)
C10—C111.5122 (19)1.5128 (16)1.5127 (16)
C14—O22—C23117.51 (11)118.12 (10)116.93 (9)
C15—C14—O22—C2311.5 (2)11.24 (17)-2.45 (17)
C4—N9—C10—C1179.64 (17)78.72 (15)-70.99 (15)
N9—C10—C11—C12-95.59 (16)-94.59 (14)91.21 (13)
Notes: (a) Braendvang & Gundersen (2007a).
 

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