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Two independent mol­ecules comprise the asymmetric unit of the title compound, C12H11N3O2. These differ in terms of the relative orientations of the benzene rings as seen in the respective dihedral angles formed between the pyridine and benzene rings [17.42 (16) and 34.64 (16)°]. Both mol­ecules are twisted about the amine–tolyl N—C bonds [respective torsion angles = 22.3 (5) and 35.9 (5)°] but only about the amine–pyridine N—C bond in the first independent mol­ecule [respective torsion angles = −11.7 (5) and 0.8 (5)°]. Intra­molecular N—H...O hydrogen bonds preclude the amine H atoms from forming significant inter­molecular inter­actions. The crystal packing features inter­molecular C—H...O and C—H...π and π–π [centroid–centroid distance: pyridine–benzene = 3.6442 (19) Å and pyridine–pyridine = 3.722 (2) Å] contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810033040/hg2703sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536810033040/hg2703Isup2.hkl
Contains datablock I

CCDC reference: 792474

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.048
  • wR factor = 0.146
  • Data-to-parameter ratio = 15.2

checkCIF/PLATON results

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Alert level C PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 33 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 54
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 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

Studies of pyridine and pyrimidine derivatives related to the title compound are of interest owing to their putative fluorescence properties (Kawai et al. 2001; Abdullah, 2005). As a continuation of structural studies on this class of N-heterocycles (Badaruddin et al., 2009; Fairuz et al., 2010), the title compound, (I), was investigated.

Two independent molecules comprise the asymmetric unit of (I), Figs 1 and 2. While the geometric parameters are in close agreement [r.m.s. deviation of bond distances and angles = 0.0080 Å and 0.849 °, respectively], these differ non-trivially in their conformations. So, while the pyridine groups are virtually super-imposable, the benzene rings are not, Fig. 3. This difference is quantified in the dihedral angles formed between the pyridine and benzene rings, i.e. N2,C1–C5/C6–C11 = 17.42 (16) ° and N5,C13–C17/C18–C23 = 34.64 (16) °. These indicate that there are also twists in the molecules as evidenced by the C6–N3–C5–N2 torsion angle of -11.7 (5) ° and, especially, the C5–N3–C6–C11 torsion angle of 22.3 (5) °. The equivalent torsion angles for the second independent molecule of C18–N6–C17–N5 = 0.8 (5) ° and C17–N6–C18–C23 = 35.9 (5) ° also highlight the differences between the molecules. The nitro groups are co-planar with the pyridine rings to which they are connected as indicated by the O1–N1–C1–C5 and O3–N4–C13–C17 torsion angles of 1.5 (5) and -1.1 (5) °, respectively. Close intramolecular N–H···O and C–H···N interactions are noted, Table 1.

The most notable intermolecular interactions in the crystal structure are of the type C–H···O [which connect the molecules comprising the asymmetric unit], C–H···π and ππ [ring centroid(N2,C1–C5)···centroid(C18–C23) = 3.6442 (19) Å and ring centroid(N5,C13–C17)···centroid(N5,C13–C17)i = 3.722 (2) Å for i: -x, 1 - y, -z] contacts. These serve to connect molecules into the three-dimensional structure, Fig. 4.

Related literature top

For background to the fluorescence properties of compounds related to the title compound, see: Kawai et al. (2001); Abdullah (2005). For the structures of related pyrimidine amine derivatives, see: Badaruddin et al., (2009); Fairuz et al. (2010).

Experimental top

2-Chloro-3-nitro-pyridine (0.7899 g, 0.005 mol) and p-toluidine (0.536 g, 0.005 mol) were refluxed in 5 ml ethanol for 5.5 h at 351 K. The mixture was cooled. The residue was then dissolved in a minimum volume of water (10 ml) and extracted with ether (3 x 10 ml). The ethereal layer was washed with water and dried over anhydrous sodium sulfate. Evaporation gave a reddish solid and recrystallization using ethyl acetate yielded red crystals.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 to 1.5Uequiv(C). The N-bound H-atoms were located in a difference Fourier map but were were refined with a distance restraint of N–H = 0.86±0.01 Å, and with unrestricted Uiso(H).

Structure description top

Studies of pyridine and pyrimidine derivatives related to the title compound are of interest owing to their putative fluorescence properties (Kawai et al. 2001; Abdullah, 2005). As a continuation of structural studies on this class of N-heterocycles (Badaruddin et al., 2009; Fairuz et al., 2010), the title compound, (I), was investigated.

Two independent molecules comprise the asymmetric unit of (I), Figs 1 and 2. While the geometric parameters are in close agreement [r.m.s. deviation of bond distances and angles = 0.0080 Å and 0.849 °, respectively], these differ non-trivially in their conformations. So, while the pyridine groups are virtually super-imposable, the benzene rings are not, Fig. 3. This difference is quantified in the dihedral angles formed between the pyridine and benzene rings, i.e. N2,C1–C5/C6–C11 = 17.42 (16) ° and N5,C13–C17/C18–C23 = 34.64 (16) °. These indicate that there are also twists in the molecules as evidenced by the C6–N3–C5–N2 torsion angle of -11.7 (5) ° and, especially, the C5–N3–C6–C11 torsion angle of 22.3 (5) °. The equivalent torsion angles for the second independent molecule of C18–N6–C17–N5 = 0.8 (5) ° and C17–N6–C18–C23 = 35.9 (5) ° also highlight the differences between the molecules. The nitro groups are co-planar with the pyridine rings to which they are connected as indicated by the O1–N1–C1–C5 and O3–N4–C13–C17 torsion angles of 1.5 (5) and -1.1 (5) °, respectively. Close intramolecular N–H···O and C–H···N interactions are noted, Table 1.

The most notable intermolecular interactions in the crystal structure are of the type C–H···O [which connect the molecules comprising the asymmetric unit], C–H···π and ππ [ring centroid(N2,C1–C5)···centroid(C18–C23) = 3.6442 (19) Å and ring centroid(N5,C13–C17)···centroid(N5,C13–C17)i = 3.722 (2) Å for i: -x, 1 - y, -z] contacts. These serve to connect molecules into the three-dimensional structure, Fig. 4.

For background to the fluorescence properties of compounds related to the title compound, see: Kawai et al. (2001); Abdullah (2005). For the structures of related pyrimidine amine derivatives, see: Badaruddin et al., (2009); Fairuz et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and Qmol (Gans & Shalloway, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of the first independent molecule in (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. The molecular structure of the second independent molecule in (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
[Figure 3] Fig. 3. Overlay diagram of the first independent molecule (shown in red) and the second independent molecule (shown in blue).
[Figure 4] Fig. 4. Unit-cell contents for (I) shown in projection down the a axis. The C–H···π and ππ contacts are shown as blue and purple dashed lines, respectively. The C–H···O interactions are largely obscured in this projection.
N-(4-Methylphenyl)-3-nitropyridin-2-amine top
Crystal data top
C12H11N3O2F(000) = 960
Mr = 229.24Dx = 1.432 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2221 reflections
a = 10.6557 (12) Åθ = 3.0–27.8°
b = 7.1415 (8) ŵ = 0.10 mm1
c = 27.958 (3) ÅT = 100 K
β = 91.310 (2)°Plate, red
V = 2127.0 (4) Å30.35 × 0.35 × 0.05 mm
Z = 8
Data collection top
Bruker SMART APEX
diffractometer
3344 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.045
Graphite monochromatorθmax = 27.5°, θmin = 1.5°
ω scansh = 1311
13178 measured reflectionsk = 89
4804 independent reflectionsl = 3636
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0685P)2 + 0.8145P]
where P = (Fo2 + 2Fc2)/3
4804 reflections(Δ/σ)max = 0.001
317 parametersΔρmax = 0.30 e Å3
2 restraintsΔρmin = 0.28 e Å3
Crystal data top
C12H11N3O2V = 2127.0 (4) Å3
Mr = 229.24Z = 8
Monoclinic, P21/cMo Kα radiation
a = 10.6557 (12) ŵ = 0.10 mm1
b = 7.1415 (8) ÅT = 100 K
c = 27.958 (3) Å0.35 × 0.35 × 0.05 mm
β = 91.310 (2)°
Data collection top
Bruker SMART APEX
diffractometer
3344 reflections with I > 2σ(I)
13178 measured reflectionsRint = 0.045
4804 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0482 restraints
wR(F2) = 0.146H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.30 e Å3
4804 reflectionsΔρmin = 0.28 e Å3
317 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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.5737 (2)0.6059 (3)0.07334 (8)0.0224 (6)
O20.3802 (2)0.6139 (4)0.04820 (8)0.0265 (6)
O30.1554 (2)0.1650 (4)0.07299 (8)0.0286 (6)
O40.0348 (2)0.2379 (4)0.09457 (8)0.0286 (6)
N10.4595 (3)0.5848 (4)0.08003 (9)0.0186 (6)
N20.4564 (3)0.4326 (4)0.20794 (9)0.0193 (6)
N30.6278 (2)0.5089 (4)0.16220 (9)0.0163 (6)
N40.0469 (3)0.2118 (4)0.06319 (9)0.0207 (6)
N50.0665 (3)0.2476 (4)0.06993 (9)0.0200 (6)
N60.2219 (3)0.1555 (4)0.01848 (9)0.0191 (6)
C10.4176 (3)0.5224 (4)0.12647 (10)0.0171 (7)
C20.2897 (3)0.4973 (5)0.13170 (11)0.0195 (7)
H20.23310.51960.10560.023*
C30.2457 (3)0.4396 (5)0.17510 (11)0.0206 (7)
H3A0.15860.42130.17980.025*
C40.3327 (3)0.4092 (5)0.21164 (11)0.0211 (7)
H40.30220.36870.24160.025*
C50.5016 (3)0.4879 (4)0.16576 (11)0.0161 (7)
C60.7235 (3)0.5118 (4)0.19792 (11)0.0154 (7)
C70.8350 (3)0.5993 (4)0.18500 (11)0.0169 (7)
H70.84270.64760.15350.020*
C80.9339 (3)0.6166 (5)0.21729 (11)0.0185 (7)
H81.00890.67590.20760.022*
C90.9263 (3)0.5489 (5)0.26396 (11)0.0179 (7)
C100.8168 (3)0.4554 (5)0.27559 (11)0.0184 (7)
H100.81060.40340.30670.022*
C110.7155 (3)0.4345 (5)0.24348 (11)0.0184 (7)
H110.64240.36860.25260.022*
C121.0323 (3)0.5790 (5)0.29973 (11)0.0224 (7)
H12A1.00970.52530.33060.034*
H12B1.04780.71350.30350.034*
H12C1.10830.51780.28830.034*
C130.0149 (3)0.2401 (5)0.01373 (11)0.0183 (7)
C140.1058 (3)0.3001 (5)0.00485 (12)0.0212 (7)
H140.16490.31520.03050.025*
C150.1398 (3)0.3376 (5)0.04115 (12)0.0220 (7)
H150.22140.38170.04820.026*
C160.0491 (3)0.3079 (5)0.07704 (12)0.0222 (7)
H160.07200.33280.10910.027*
C170.1032 (3)0.2129 (4)0.02481 (11)0.0172 (7)
C180.3186 (3)0.1221 (5)0.05334 (11)0.0173 (7)
C190.4414 (3)0.1571 (5)0.03961 (11)0.0189 (7)
H190.45680.20630.00870.023*
C200.5413 (3)0.1203 (5)0.07102 (11)0.0188 (7)
H200.62460.14230.06100.023*
C210.5218 (3)0.0519 (5)0.11668 (11)0.0179 (7)
C220.3992 (3)0.0150 (5)0.12938 (11)0.0188 (7)
H220.38400.03400.16030.023*
C230.2979 (3)0.0474 (5)0.09839 (11)0.0201 (7)
H230.21510.01870.10790.024*
C240.6290 (3)0.0200 (5)0.15168 (12)0.0242 (8)
H24A0.70840.02200.13470.036*
H24B0.61890.10190.16720.036*
H24C0.62960.11900.17590.036*
H30.652 (3)0.552 (5)0.1350 (8)0.022 (10)*
H60.242 (3)0.153 (6)0.0118 (14)0.031 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0175 (13)0.0287 (14)0.0210 (11)0.0020 (10)0.0014 (9)0.0037 (10)
O20.0236 (13)0.0349 (15)0.0206 (11)0.0030 (11)0.0063 (10)0.0061 (10)
O30.0235 (14)0.0429 (16)0.0195 (12)0.0097 (12)0.0008 (10)0.0016 (11)
O40.0288 (14)0.0353 (15)0.0212 (12)0.0007 (12)0.0093 (10)0.0011 (10)
N10.0209 (15)0.0172 (15)0.0178 (13)0.0010 (12)0.0025 (11)0.0008 (10)
N20.0189 (15)0.0212 (15)0.0179 (13)0.0001 (12)0.0012 (11)0.0003 (11)
N30.0131 (14)0.0217 (15)0.0140 (12)0.0016 (11)0.0009 (10)0.0025 (10)
N40.0220 (16)0.0199 (15)0.0200 (13)0.0018 (12)0.0040 (11)0.0017 (11)
N50.0177 (15)0.0224 (15)0.0198 (13)0.0022 (12)0.0000 (11)0.0008 (11)
N60.0172 (15)0.0254 (16)0.0147 (13)0.0025 (12)0.0024 (11)0.0008 (11)
C10.0215 (18)0.0143 (16)0.0156 (14)0.0000 (13)0.0000 (12)0.0003 (12)
C20.0172 (17)0.0174 (17)0.0236 (16)0.0017 (13)0.0046 (13)0.0006 (13)
C30.0127 (17)0.0218 (18)0.0274 (17)0.0001 (14)0.0007 (13)0.0011 (14)
C40.0199 (18)0.0232 (18)0.0203 (15)0.0021 (14)0.0024 (13)0.0003 (13)
C50.0170 (17)0.0141 (16)0.0173 (14)0.0002 (13)0.0004 (12)0.0032 (11)
C60.0116 (16)0.0171 (16)0.0173 (14)0.0012 (13)0.0018 (12)0.0027 (12)
C70.0172 (17)0.0164 (16)0.0171 (14)0.0009 (13)0.0009 (12)0.0004 (12)
C80.0167 (17)0.0159 (17)0.0229 (16)0.0000 (13)0.0002 (13)0.0001 (12)
C90.0185 (17)0.0151 (16)0.0198 (15)0.0028 (13)0.0025 (12)0.0041 (12)
C100.0198 (18)0.0206 (17)0.0149 (14)0.0042 (14)0.0019 (12)0.0002 (12)
C110.0171 (17)0.0192 (17)0.0189 (15)0.0007 (14)0.0014 (12)0.0001 (13)
C120.0232 (19)0.0211 (18)0.0227 (16)0.0005 (15)0.0064 (14)0.0014 (13)
C130.0208 (18)0.0162 (16)0.0180 (15)0.0029 (14)0.0017 (12)0.0009 (12)
C140.0195 (18)0.0172 (17)0.0265 (17)0.0050 (14)0.0046 (13)0.0044 (13)
C150.0148 (17)0.0204 (18)0.0309 (18)0.0001 (14)0.0025 (14)0.0040 (14)
C160.0219 (18)0.0226 (18)0.0222 (16)0.0002 (15)0.0038 (13)0.0028 (13)
C170.0181 (17)0.0144 (16)0.0190 (15)0.0022 (13)0.0026 (12)0.0020 (12)
C180.0205 (18)0.0145 (16)0.0168 (14)0.0019 (13)0.0017 (12)0.0019 (12)
C190.0236 (18)0.0169 (17)0.0162 (14)0.0005 (14)0.0032 (12)0.0010 (12)
C200.0124 (16)0.0218 (18)0.0223 (16)0.0000 (13)0.0024 (12)0.0021 (13)
C210.0172 (17)0.0150 (16)0.0214 (15)0.0029 (13)0.0036 (13)0.0040 (12)
C220.0186 (17)0.0214 (18)0.0165 (14)0.0020 (14)0.0011 (12)0.0030 (12)
C230.0167 (17)0.0219 (18)0.0217 (15)0.0006 (14)0.0023 (13)0.0030 (13)
C240.0235 (19)0.0256 (19)0.0232 (16)0.0044 (15)0.0049 (14)0.0019 (14)
Geometric parameters (Å, º) top
O1—N11.245 (3)C9—C101.389 (5)
O2—N11.230 (3)C9—C121.507 (4)
O3—N41.240 (4)C10—C111.396 (4)
O4—N41.236 (3)C10—H100.9500
N1—C11.452 (4)C11—H110.9500
N2—C41.335 (4)C12—H12A0.9800
N2—C51.343 (4)C12—H12B0.9800
N3—C51.359 (4)C12—H12C0.9800
N3—C61.412 (4)C13—C141.383 (5)
N3—H30.867 (15)C13—C171.428 (4)
N4—C131.446 (4)C14—C151.370 (5)
N5—C161.324 (4)C14—H140.9500
N5—C171.352 (4)C15—C161.393 (5)
N6—C171.345 (4)C15—H150.9500
N6—C181.422 (4)C16—H160.9500
N6—H60.88 (4)C18—C231.390 (4)
C1—C21.386 (5)C18—C191.394 (4)
C1—C51.422 (4)C19—C201.390 (4)
C2—C31.374 (4)C19—H190.9500
C2—H20.9500C20—C211.387 (4)
C3—C41.380 (4)C20—H200.9500
C3—H3A0.9500C21—C221.388 (4)
C4—H40.9500C21—C241.505 (4)
C6—C111.393 (4)C22—C231.388 (4)
C6—C71.397 (4)C22—H220.9500
C7—C81.377 (4)C23—H230.9500
C7—H70.9500C24—H24A0.9800
C8—C91.396 (4)C24—H24B0.9800
C8—H80.9500C24—H24C0.9800
O2—N1—O1121.9 (3)C10—C11—H11120.5
O2—N1—C1118.6 (3)C9—C12—H12A109.5
O1—N1—C1119.5 (2)C9—C12—H12B109.5
C4—N2—C5118.6 (3)H12A—C12—H12B109.5
C5—N3—C6130.6 (3)C9—C12—H12C109.5
C5—N3—H3115 (2)H12A—C12—H12C109.5
C6—N3—H3113 (2)H12B—C12—H12C109.5
O4—N4—O3121.9 (3)C14—C13—C17120.4 (3)
O4—N4—C13118.7 (3)C14—C13—N4117.1 (3)
O3—N4—C13119.4 (3)C17—C13—N4122.5 (3)
C16—N5—C17119.3 (3)C15—C14—C13119.7 (3)
C17—N6—C18129.0 (3)C15—C14—H14120.2
C17—N6—H6113 (3)C13—C14—H14120.2
C18—N6—H6118 (3)C14—C15—C16116.9 (3)
C2—C1—C5119.9 (3)C14—C15—H15121.5
C2—C1—N1117.2 (3)C16—C15—H15121.5
C5—C1—N1122.9 (3)N5—C16—C15125.0 (3)
C3—C2—C1119.2 (3)N5—C16—H16117.5
C3—C2—H2120.4C15—C16—H16117.5
C1—C2—H2120.4N6—C17—N5118.1 (3)
C2—C3—C4117.7 (3)N6—C17—C13123.2 (3)
C2—C3—H3A121.2N5—C17—C13118.6 (3)
C4—C3—H3A121.2C23—C18—C19119.2 (3)
N2—C4—C3124.8 (3)C23—C18—N6123.9 (3)
N2—C4—H4117.6C19—C18—N6116.8 (3)
C3—C4—H4117.6C20—C19—C18120.2 (3)
N2—C5—N3118.2 (3)C20—C19—H19119.9
N2—C5—C1119.8 (3)C18—C19—H19119.9
N3—C5—C1122.0 (3)C21—C20—C19121.3 (3)
C11—C6—C7119.0 (3)C21—C20—H20119.3
C11—C6—N3125.7 (3)C19—C20—H20119.3
C7—C6—N3115.4 (3)C22—C21—C20117.7 (3)
C8—C7—C6120.8 (3)C22—C21—C24120.7 (3)
C8—C7—H7119.6C20—C21—C24121.6 (3)
C6—C7—H7119.6C21—C22—C23122.1 (3)
C7—C8—C9121.5 (3)C21—C22—H22118.9
C7—C8—H8119.3C23—C22—H22118.9
C9—C8—H8119.3C22—C23—C18119.5 (3)
C10—C9—C8116.9 (3)C22—C23—H23120.2
C10—C9—C12122.3 (3)C18—C23—H23120.2
C8—C9—C12120.8 (3)C21—C24—H24A109.5
C9—C10—C11122.8 (3)C21—C24—H24B109.5
C9—C10—H10118.6H24A—C24—H24B109.5
C11—C10—H10118.6C21—C24—H24C109.5
C6—C11—C10118.9 (3)H24A—C24—H24C109.5
C6—C11—H11120.5H24B—C24—H24C109.5
O2—N1—C1—C20.8 (4)O4—N4—C13—C141.7 (4)
O1—N1—C1—C2178.6 (3)O3—N4—C13—C14177.3 (3)
O2—N1—C1—C5179.0 (3)O4—N4—C13—C17179.9 (3)
O1—N1—C1—C51.5 (5)O3—N4—C13—C171.1 (5)
C5—C1—C2—C30.3 (5)C17—C13—C14—C151.4 (5)
N1—C1—C2—C3179.6 (3)N4—C13—C14—C15177.0 (3)
C1—C2—C3—C40.1 (5)C13—C14—C15—C161.5 (5)
C5—N2—C4—C30.7 (5)C17—N5—C16—C150.9 (5)
C2—C3—C4—N20.3 (5)C14—C15—C16—N50.4 (5)
C4—N2—C5—N3179.1 (3)C18—N6—C17—N50.8 (5)
C4—N2—C5—C10.8 (5)C18—N6—C17—C13179.7 (3)
C6—N3—C5—N211.7 (5)C16—N5—C17—N6178.6 (3)
C6—N3—C5—C1168.4 (3)C16—N5—C17—C130.9 (5)
C2—C1—C5—N20.6 (5)C14—C13—C17—N6179.7 (3)
N1—C1—C5—N2179.2 (3)N4—C13—C17—N61.4 (5)
C2—C1—C5—N3179.3 (3)C14—C13—C17—N50.2 (5)
N1—C1—C5—N30.8 (5)N4—C13—C17—N5178.1 (3)
C5—N3—C6—C1122.3 (5)C17—N6—C18—C2335.9 (5)
C5—N3—C6—C7158.4 (3)C17—N6—C18—C19148.1 (3)
C11—C6—C7—C82.8 (5)C23—C18—C19—C201.0 (5)
N3—C6—C7—C8177.8 (3)N6—C18—C19—C20177.3 (3)
C6—C7—C8—C90.5 (5)C18—C19—C20—C211.3 (5)
C7—C8—C9—C103.1 (5)C19—C20—C21—C222.3 (5)
C7—C8—C9—C12176.3 (3)C19—C20—C21—C24177.1 (3)
C8—C9—C10—C112.6 (5)C20—C21—C22—C231.1 (5)
C12—C9—C10—C11176.8 (3)C24—C21—C22—C23178.3 (3)
C7—C6—C11—C103.2 (5)C21—C22—C23—C181.1 (5)
N3—C6—C11—C10177.4 (3)C19—C18—C23—C222.2 (5)
C9—C10—C11—C60.6 (5)N6—C18—C23—C22178.1 (3)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C6–C11 ring.
D—H···AD—HH···AD···AD—H···A
N3—H3···O10.87 (3)1.94 (3)2.630 (3)136 (3)
N6—H6···O30.88 (4)1.93 (4)2.639 (3)137 (3)
N3—H3···N10.87 (3)2.55 (3)2.932 (4)108 (2)
N6—H6···N40.88 (4)2.54 (4)2.942 (4)109 (2)
C14—H14···O2i0.952.393.199 (4)143
C4—H4···Cg1ii0.952.903.604 (4)132
C12—H12b···Cg1iii0.982.803.654 (4)146
Symmetry codes: (i) x, y+1, z; (ii) x+1, y1/2, z+1/2; (iii) x+2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC12H11N3O2
Mr229.24
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)10.6557 (12), 7.1415 (8), 27.958 (3)
β (°) 91.310 (2)
V3)2127.0 (4)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.35 × 0.35 × 0.05
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
13178, 4804, 3344
Rint0.045
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.146, 1.04
No. of reflections4804
No. of parameters317
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.30, 0.28

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and Qmol (Gans & Shalloway, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C6–C11 ring.
D—H···AD—HH···AD···AD—H···A
N3—H3···O10.87 (3)1.94 (3)2.630 (3)136 (3)
N6—H6···O30.88 (4)1.93 (4)2.639 (3)137 (3)
N3—H3···N10.87 (3)2.55 (3)2.932 (4)108 (2)
N6—H6···N40.88 (4)2.54 (4)2.942 (4)109 (2)
C14—H14···O2i0.952.393.199 (4)143
C4—H4···Cg1ii0.952.903.604 (4)132
C12—H12b···Cg1iii0.982.803.654 (4)146
Symmetry codes: (i) x, y+1, z; (ii) x+1, y1/2, z+1/2; (iii) x+2, y+1/2, z+1/2.
 

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