organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

2,2-Di­methyl-2,3-di­hydro-1H-perimidine

aEaStCHEM School of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, Scotland
*Correspondence e-mail: jdw3@st-and.ac.uk

(Received 20 December 2012; accepted 10 January 2013; online 19 January 2013)

The title compound, C13H14N2, was obtained from reaction of diaminona­phthalene with acetone. In both independent mol­ecules in the asymmetric unit, the tricyclic perimidine consists of a planar (r.m.s. deviations = 0.0125 and 0.0181 Å) naphthalene ring system and an envelope conformation C4N2 ringwith the NCN group hinged with respect to the naph­thalene backbone by 36.9 (2) and 41.3 (2)° in the two independent molecules. The methyl substituents are arranged approximately axial and equatorial on the apical C atom. In the crystal, one of the N—H groups of one independent mol­ecule is involved in classical N—H⋯N hydrogen bonding. Short inter­molecular (C/N)—H⋯π(arene) inter­actions, near the short T-shaped limit, link mol­ecules in the absence of strong acceptors.

Related literature

For general background to perimidines and their biological activity, see: Shaabani & Maleki (2008[Shaabani, A. & Maleki, A. (2008). Chem. Pharm. Bull. 56, 79-81.]); Sauer et al. (2006[Sauer, M., Yeung, C., Lai, C.-C. & Chiu, S.-H. (2006). J. Org. Chem. 71, 775-788.]). For related structures, see: Martinez-Belmonte et al. (2010[Martinez-Belmonte, M., Escudero-Adan, E. C., Benet-Buchholz, J., Haak, R. M. & Kleij, A. W. (2010). Eur. J. Inorg. Chem. pp. 4823-4831.]).

[Scheme 1]

Experimental

Crystal data
  • C13H14N2

  • Mr = 198.27

  • Monoclinic, P 21 /c

  • a = 16.261 (10) Å

  • b = 7.710 (4) Å

  • c = 17.483 (10) Å

  • β = 106.131 (12)°

  • V = 2105.6 (19) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 93 K

  • 0.12 × 0.12 × 0.12 mm

Data collection
  • Rigaku Mercury70 diffractometer

  • Absorption correction: multi-scan (REQAB; Rigaku, 1998[Rigaku (1998). REQAB. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.706, Tmax = 0.991

  • 12841 measured reflections

  • 3743 independent reflections

  • 2356 reflections with F2 > 2σ(F2)

  • Rint = 0.072

Refinement
  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.133

  • S = 0.96

  • 3743 reflections

  • 287 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C21–C25/C30, C25–C30 and C5–C10 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N21—H21N⋯N29i 0.88 (2) 2.36 (2) 3.229 (4) 170 (2)
N1—H1N⋯Cg1ii 0.93 (3) 2.93 (3) 3.853 (3) 170 (2)
N9—H9N⋯Cg1 0.88 (4) 2.85 (2) 3.703 (3) 164 (2)
C12—H12CCg2 0.98 2.55 3.521 (3) 172
C26—H26⋯Cg3iii 0.95 2.53 3.456 (3) 164
Symmetry codes: (i) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) x, y-1, z.

Data collection: CrystalClear-SM Expert (Rigaku, 2009[Rigaku (2009). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SIR2002 (Burla et al., 2003[Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); software used to prepare material for publication: CrystalStructure.

Supporting information


Comment top

The title compound has a planar napthalene backbone with the the nitrogen atoms above this plane in both independent molecules (N1 0.133, N9 0.182, N21 0.155, N290.047 Å) and the carbon in the C4N2 ring being below this plane (C11 - 0.373, C31 - 0.488 Å). The six membered C4N2 ring is hinged about the N···N vector with the N1—C11—N9 and C21—C31—N29 planes being inclined by 36.9 and 41.0° respectively to the naphthalene planes.

Related literature top

For general background to perimidines and their biological activity, see: Shaabani & Maleki (2008); Sauer et al. (2006). For related structures, see: Martinez-Belmonte et al. (2010)

Experimental top

A solution of 1,8-aminonapthalene (1.52 g, 0.01 mol s) and acetone (0.58 g, 0.78 ml, 0.01 mol s) was refluxed in ethanol (50 ml) for 2 h. The solution was then filtered, solvent evaporated to dryness under reduced pressure and recrystallized from boiling ethanol to give translucent crystals (mp xoC). (0.897 g, 0.0045 mol s, 45%). IR (KBr disc): 3295 ν(N—H), 1596 aromatic C—H, 1016, 646, 552, 477 cm-1. Raman (solid sample): 1490, 447, 160 cm-1. δH (270.0 MHz, CDCl3, Me4Si): 7.24–7.14 (4H, m, H1, H2), 6.47–6.44 (2H, dd, H3), 4.16 (2H, brd s, H4), 1.49 (6H, s, H5). δC (75.5 MHz, CDCl3, Me4Si): 140.4 (2 C, C4), 127.1 (2 C,C3), 117.2 (2 C, C2), 106.1 (2 C, C1), 64.7 (1 C, C5), 28.9 (2 C, C6). MS EI+: m/z 221.05 (M+ + Na)+ , 199.06 (M+ + H)+, 182.08 (M+ - Me)+. Found: C, 78.27; H, 6.93 N, 14.21. C13H14N2 requires C, 78.75; H, 7.12; N, 14.13%.

Refinement top

All H atoms were included in calculated positions (C—H distances are 0.98 Å for methyl H atoms, 0.95 Å for phenyl H atoms) and were refined as riding atoms with Uiso(H) = 1.2 Ueq(parent atom, methylene H atoms) or Uiso(H) = 1.5 Ueq(parent atom, methyl H atoms). The highest peak in the difference map is 0.94 Å from atom C29.

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku, 2009); cell refinement: CrystalClear-SM Expert (Rigaku, 2009); data reduction: CrystalClear-SM Expert (Rigaku, 2009); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top
[Figure 1] Fig. 1. The structure of (1) with displacement ellipsoids drawn at the 50% probability level
2,2-Dimethyl-2,3-dihydro-1H-perimidine top
Crystal data top
C13H14N2F(000) = 848.00
Mr = 198.27Dx = 1.251 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybcCell parameters from 4713 reflections
a = 16.261 (10) Åθ = 2.4–25.4°
b = 7.710 (4) ŵ = 0.08 mm1
c = 17.483 (10) ÅT = 93 K
β = 106.131 (12)°Prism, colorless
V = 2105.6 (19) Å30.12 × 0.12 × 0.12 mm
Z = 8
Data collection top
Rigaku Mercury70
diffractometer
2356 reflections with F2 > 2σ(F2)
Detector resolution: 14.629 pixels mm-1Rint = 0.072
ω scansθmax = 25.1°
Absorption correction: multi-scan
(REQAB; Rigaku, 1998)
h = 1919
Tmin = 0.706, Tmax = 0.991k = 99
12841 measured reflectionsl = 2016
3743 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H atoms treated by a mixture of independent and constrained refinement
S = 0.96 w = 1/[σ2(Fo2) + (0.0447P)2]
where P = (Fo2 + 2Fc2)/3
3743 reflections(Δ/σ)max < 0.001
287 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.24 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C13H14N2V = 2105.6 (19) Å3
Mr = 198.27Z = 8
Monoclinic, P21/cMo Kα radiation
a = 16.261 (10) ŵ = 0.08 mm1
b = 7.710 (4) ÅT = 93 K
c = 17.483 (10) Å0.12 × 0.12 × 0.12 mm
β = 106.131 (12)°
Data collection top
Rigaku Mercury70
diffractometer
3743 independent reflections
Absorption correction: multi-scan
(REQAB; Rigaku, 1998)
2356 reflections with F2 > 2σ(F2)
Tmin = 0.706, Tmax = 0.991Rint = 0.072
12841 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.133H atoms treated by a mixture of independent and constrained refinement
S = 0.96Δρmax = 0.22 e Å3
3743 reflectionsΔρmin = 0.24 e Å3
287 parameters
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.74130 (13)0.4938 (3)0.32012 (12)0.0251 (5)
N90.72027 (13)0.4474 (3)0.44670 (12)0.0253 (5)
C10.67357 (15)0.6139 (3)0.29931 (14)0.0239 (6)
C20.65289 (15)0.7024 (3)0.22781 (14)0.0257 (6)
C30.58887 (16)0.8304 (3)0.21297 (15)0.0293 (6)
C40.54615 (16)0.8709 (3)0.26806 (15)0.0276 (6)
C50.56482 (15)0.7808 (3)0.34165 (14)0.0245 (6)
C60.52239 (16)0.8170 (3)0.40084 (15)0.0296 (7)
C70.54224 (15)0.7241 (3)0.47065 (15)0.0304 (7)
C80.60553 (16)0.5958 (3)0.48627 (15)0.0280 (6)
C90.64967 (15)0.5602 (3)0.43120 (14)0.0240 (6)
C100.62879 (15)0.6508 (3)0.35711 (14)0.0225 (6)
C110.73892 (16)0.3581 (3)0.37924 (14)0.0255 (6)
C120.82772 (15)0.2789 (3)0.40713 (15)0.0301 (7)
C130.67145 (15)0.2193 (3)0.34472 (14)0.0286 (7)
H20.68180.67680.18880.0309*
H30.57490.89040.16360.0351*
H40.50390.95950.25690.0331*
H60.48020.90560.39210.0355*
H70.51230.74750.50910.0364*
H80.61810.53310.53490.0336*
H12A0.86920.36880.43200.0361*
H12B0.84340.22960.36140.0361*
H12C0.82800.18720.44600.0361*
H13A0.68460.16340.29920.0343*
H13B0.61480.27350.32720.0343*
H13C0.67180.13220.38560.0343*
H9n0.7242 (16)0.381 (3)0.4888 (15)0.035 (8)*
H1n0.7596 (16)0.455 (3)0.2770 (16)0.043 (8)*
N210.95216 (13)0.2662 (3)0.72018 (12)0.0237 (5)
N291.01370 (14)0.0717 (3)0.64843 (12)0.0240 (5)
C210.86940 (15)0.2322 (3)0.67450 (13)0.0213 (6)
C220.79708 (15)0.3089 (3)0.68648 (14)0.0236 (6)
C230.71473 (16)0.2555 (3)0.64207 (14)0.0255 (6)
C240.70369 (15)0.1272 (3)0.58569 (14)0.0259 (6)
C250.77628 (15)0.0457 (3)0.57089 (14)0.0222 (6)
C260.76848 (16)0.0902 (3)0.51485 (14)0.0267 (6)
C270.84036 (16)0.1676 (3)0.50372 (14)0.0277 (6)
C280.92278 (16)0.1122 (3)0.54540 (14)0.0252 (6)
C290.93299 (15)0.0203 (3)0.60052 (14)0.0225 (6)
C300.85910 (15)0.1007 (3)0.61425 (13)0.0200 (6)
C311.02152 (15)0.2496 (3)0.68135 (14)0.0235 (6)
C321.10655 (15)0.2637 (3)0.74320 (15)0.0303 (7)
C331.01217 (16)0.3872 (3)0.61631 (14)0.0281 (7)
H21n0.9598 (16)0.359 (3)0.7505 (15)0.033 (8)*
H29n1.0552 (17)0.048 (3)0.6295 (15)0.039 (9)*
H220.80300.39830.72500.0283*
H230.66590.30940.65140.0305*
H240.64760.09280.55660.0311*
H260.71330.12790.48480.0320*
H270.83410.26080.46700.0332*
H280.97160.16570.53570.0303*
H32A1.15270.24100.71850.0364*
H32B1.10930.17850.78540.0364*
H32C1.11310.38070.76600.0364*
H33A1.01520.50300.64010.0337*
H33B0.95680.37290.57630.0337*
H33C1.05840.37380.59090.0337*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0277 (14)0.0244 (11)0.0255 (13)0.0014 (10)0.0114 (11)0.0024 (10)
N90.0296 (14)0.0263 (12)0.0200 (13)0.0024 (10)0.0065 (11)0.0030 (10)
C10.0197 (15)0.0222 (13)0.0300 (15)0.0044 (11)0.0073 (12)0.0033 (11)
C20.0266 (16)0.0271 (13)0.0236 (14)0.0037 (12)0.0072 (13)0.0006 (11)
C30.0304 (16)0.0283 (14)0.0254 (15)0.0047 (12)0.0016 (13)0.0028 (11)
C40.0243 (15)0.0222 (13)0.0338 (16)0.0018 (11)0.0038 (13)0.0008 (12)
C50.0197 (14)0.0227 (13)0.0301 (15)0.0053 (11)0.0049 (12)0.0033 (11)
C60.0227 (15)0.0279 (14)0.0383 (17)0.0020 (12)0.0087 (14)0.0029 (12)
C70.0278 (16)0.0334 (15)0.0337 (16)0.0032 (12)0.0149 (14)0.0030 (12)
C80.0292 (16)0.0295 (14)0.0283 (16)0.0024 (12)0.0130 (13)0.0012 (11)
C90.0257 (16)0.0211 (13)0.0245 (15)0.0055 (11)0.0063 (13)0.0012 (10)
C100.0202 (15)0.0199 (12)0.0264 (14)0.0047 (11)0.0050 (12)0.0019 (11)
C110.0246 (15)0.0269 (13)0.0246 (15)0.0007 (11)0.0062 (13)0.0006 (11)
C120.0272 (16)0.0318 (14)0.0316 (16)0.0002 (12)0.0088 (13)0.0015 (12)
C130.0280 (16)0.0259 (13)0.0313 (16)0.0016 (12)0.0071 (13)0.0013 (11)
N210.0212 (13)0.0263 (12)0.0237 (13)0.0023 (10)0.0066 (11)0.0048 (9)
N290.0204 (13)0.0239 (11)0.0271 (13)0.0013 (10)0.0054 (11)0.0041 (9)
C210.0203 (15)0.0220 (13)0.0213 (14)0.0019 (11)0.0055 (12)0.0038 (10)
C220.0233 (15)0.0251 (13)0.0227 (14)0.0007 (11)0.0069 (12)0.0021 (11)
C230.0249 (16)0.0282 (14)0.0260 (15)0.0025 (11)0.0115 (13)0.0073 (11)
C240.0190 (15)0.0329 (14)0.0261 (15)0.0030 (11)0.0068 (13)0.0047 (12)
C250.0204 (15)0.0250 (13)0.0219 (14)0.0015 (11)0.0071 (12)0.0049 (11)
C260.0244 (15)0.0253 (13)0.0285 (16)0.0070 (11)0.0043 (13)0.0015 (11)
C270.0318 (17)0.0213 (13)0.0303 (16)0.0042 (12)0.0092 (13)0.0050 (11)
C280.0256 (16)0.0239 (13)0.0274 (15)0.0005 (11)0.0093 (13)0.0021 (11)
C290.0213 (15)0.0234 (13)0.0233 (14)0.0014 (11)0.0069 (12)0.0034 (11)
C300.0229 (15)0.0168 (12)0.0212 (14)0.0017 (11)0.0078 (12)0.0034 (10)
C310.0197 (15)0.0251 (13)0.0264 (14)0.0018 (11)0.0074 (12)0.0033 (11)
C320.0227 (15)0.0332 (14)0.0351 (16)0.0022 (12)0.0081 (13)0.0054 (12)
C330.0278 (16)0.0281 (14)0.0297 (16)0.0033 (12)0.0102 (13)0.0024 (11)
Geometric parameters (Å, º) top
N1—C11.407 (3)C29—C301.430 (4)
N1—C111.479 (4)C31—C321.504 (3)
N9—C91.406 (3)C31—C331.531 (4)
N9—C111.468 (4)N1—H1n0.93 (3)
C1—C21.381 (4)N9—H9n0.88 (3)
C1—C101.429 (4)C2—H20.950
C2—C31.405 (4)C3—H30.950
C3—C41.371 (5)C4—H40.950
C4—C51.418 (4)C6—H60.950
C5—C61.422 (4)C7—H70.950
C5—C101.416 (4)C8—H80.950
C6—C71.374 (4)C12—H12A0.980
C7—C81.398 (4)C12—H12B0.980
C8—C91.379 (4)C12—H12C0.980
C9—C101.427 (4)C13—H13A0.980
C11—C121.518 (4)C13—H13B0.980
C11—C131.532 (4)C13—H13C0.980
N21—C211.386 (3)N21—H21n0.88 (3)
N21—C311.475 (4)N29—H29n0.85 (3)
N29—C291.404 (3)C22—H220.950
N29—C311.480 (3)C23—H230.950
C21—C221.383 (4)C24—H240.950
C21—C301.438 (3)C26—H260.950
C22—C231.410 (4)C27—H270.950
C23—C241.373 (4)C28—H280.950
C24—C251.423 (4)C32—H32A0.980
C25—C261.416 (4)C32—H32B0.980
C25—C301.414 (3)C32—H32C0.980
C26—C271.374 (4)C33—H33A0.980
C27—C281.402 (4)C33—H33B0.980
C28—C291.382 (4)C33—H33C0.980
N1···C92.804 (4)H8···C7xi3.2563
N9···C12.789 (4)H8···H2xii3.4300
C1···C42.808 (4)H8···H3xii2.6041
C1···C133.147 (4)H8···H7xi2.9778
C2···C52.822 (4)H8···C232.9872
C3···C102.789 (4)H8···C243.4399
C5···C82.817 (4)H8···H232.6159
C6···C92.806 (4)H8···H243.4350
C7···C102.791 (4)H8···H26iii3.2782
C9···C133.101 (4)H12A···C333.4131
C10···C112.840 (4)H12A···C33ii2.9801
C10···C133.418 (4)H12A···H27iii3.0090
N21···C292.776 (4)H12A···H28xiii2.9433
N29···C212.800 (4)H12A···H33Aii2.7227
C21···C242.829 (4)H12A···H33B2.5307
C21···C333.028 (4)H12A···H33Bii3.4961
C22···C252.817 (4)H12A···H33C3.5273
C23···C302.794 (4)H12A···H33Cii2.3971
C25···C282.819 (4)H12B···N21i3.4143
C26···C292.810 (4)H12B···N29xiii3.3243
C27···C302.789 (4)H12B···C21i3.4228
C29···C333.089 (4)H12B···C22i2.9547
C30···C312.819 (4)H12B···H21ni3.1389
C30···C333.321 (4)H12B···H29nxiii2.6812
N1···C22i3.593 (4)H12B···H22i2.4947
N1···C23i3.581 (4)H12B···H28xiii3.0861
N1···C32ii3.516 (4)H12B···H33Aii3.0943
N9···C243.526 (4)H12B···H33Cii3.4433
N9···C27iii3.541 (4)H12C···C252.7718
C4···C13iii3.413 (4)H12C···C262.7575
C8···C26iii3.521 (4)H12C···C272.9033
C9···C26iii3.401 (4)H12C···C283.0393
C13···C4iv3.413 (4)H12C···C293.0507
N21···N29v3.229 (3)H12C···C302.9201
N29···N21vi3.229 (3)H12C···H29nxiii3.1687
C22···N1vii3.593 (4)H12C···H263.2466
C23···N1vii3.581 (4)H12C···H273.4716
C24···N93.526 (4)H12C···H28xiii3.1900
C26···C8iv3.521 (4)H12C···H33B2.9969
C26···C9iv3.401 (4)H13A···C3iv3.1595
C27···N9iv3.541 (4)H13A···C4iv3.1260
C29···C32vi3.573 (4)H13A···H3iv3.2995
C30···C32vi3.535 (4)H13A···H4iv3.2321
C32···N1ii3.516 (4)H13A···C22i3.0453
C32···C29v3.573 (4)H13A···C23i2.9871
C32···C30v3.535 (4)H13A···H22i2.6455
N1···H22.6386H13A···H23i2.5254
N1···H12A2.6111H13B···C3viii3.2186
N1···H12B2.6002H13B···C4iv3.3632
N1···H12C3.2706H13B···C4viii2.7866
N1···H13A2.6998H13B···C5viii3.5298
N1···H13B2.6978H13B···H3viii3.2593
N1···H13C3.3294H13B···H4iv3.0647
N1···H9n3.16 (3)H13B···H4viii2.5235
N9···H82.6451H13B···H23i3.4602
N9···H12A2.5773H13C···C4iv3.1820
N9···H12B3.2719H13C···C5iv3.1957
N9···H12C2.6654H13C···C6iv3.4981
N9···H13A3.3094H13C···H4iv3.2978
N9···H13B2.6666H13C···C243.3904
N9···H13C2.6832H13C···C253.2808
N9···H1n3.20 (3)H13C···C262.9227
C1···H33.2611H13C···H243.1356
C1···H13A3.4788H13C···H262.6146
C1···H13B2.8816H9n···C223.37 (3)
C2···H43.2775H9n···C232.89 (3)
C2···H1n2.56 (3)H9n···C242.67 (3)
C4···H23.2743H9n···C252.96 (3)
C4···H62.6865H9n···C303.41 (3)
C5···H33.2735H9n···H233.2829
C5···H73.2793H9n···H242.9522
C6···H42.6848H9n···H27iii3.3681
C6···H83.2684H1n···C21i3.20 (3)
C8···H63.2718H1n···C22i2.75 (3)
C8···H9n2.53 (3)H1n···C23i2.79 (3)
C9···H73.2583H1n···C24i3.27 (3)
C9···H13B2.8178H1n···C32ii3.16 (3)
C9···H13C3.4372H1n···H22i3.0137
C10···H23.2938H1n···H23i3.0707
C10···H43.2984H1n···H32Aii2.7368
C10···H63.3005H1n···H32Cii2.7066
C10···H83.2887H1n···H33Aii3.5589
C10···H13B2.9537H1n···H33Cii3.4702
C10···H9n3.17 (3)N21···H12Bvii3.4143
C10···H1n3.23 (3)N21···H21nvi3.43 (3)
C12···H13A2.7073N21···H29nv3.44 (3)
C12···H13B3.3548N21···H32Bv3.3261
C12···H13C2.7058N21···H32Cvi3.1878
C12···H9n2.61 (3)N21···H33Avi3.1063
C12···H1n2.61 (3)N29···H12Bxiii3.3243
C13···H12A3.3566N29···H21nvi2.36 (3)
C13···H12B2.7297N29···H22vi3.4504
C13···H12C2.6775N29···H28xiii3.3733
C13···H9n2.73 (3)N29···H32Cvi3.2210
C13···H1n2.77 (3)C21···H12Bvii3.4228
H2···H32.3459C21···H1nvii3.20 (3)
H2···H1n2.4150C21···H32Bv3.5102
H3···H42.3076C21···H32Cvi2.8885
H4···H62.5325C22···H12Bvii2.9547
H6···H72.3131C22···H13Avii3.0453
H7···H82.3375C22···H9n3.37 (3)
H8···H9n2.4025C22···H1nvii2.75 (3)
H12A···H13C3.5835C22···H32Bv3.2046
H12A···H9n2.8024C23···H2vii3.5084
H12A···H1n2.8756C23···H6xi3.3009
H12B···H13A2.5585C23···H82.9872
H12B···H13C3.0303C23···H13Avii2.9871
H12B···H9n3.5319C23···H9n2.89 (3)
H12B···H1n2.4339C23···H1nvii2.79 (3)
H12C···H13A2.9546C24···H2vii3.0379
H12C···H13B3.5735C24···H6xi3.1308
H12C···H13C2.5009C24···H7xi3.5757
H12C···H9n2.5185C24···H83.4399
H12C···H1n3.5197C24···H13C3.3904
H13A···H1n2.6343C24···H9n2.67 (3)
H13B···H9n3.0071C24···H1nvii3.27 (3)
H13B···H1n3.0686C25···H2vii3.3639
H13C···H9n2.6096C25···H12C2.7718
N21···H29n3.10 (3)C25···H13C3.2808
N21···H222.6543C25···H9n2.96 (3)
N21···H32A3.2749C25···H32Cvi3.1837
N21···H32B2.5816C26···H12C2.7575
N21···H32C2.6660C26···H13C2.9227
N21···H33A2.6732C27···H12C2.9033
N21···H33B2.6669C27···H29nxiii3.37 (3)
N21···H33C3.3100C27···H33Cxiii3.0795
N29···H21n3.12 (3)C28···H12C3.0393
N29···H282.6364C28···H21nvi3.56 (3)
N29···H32A2.6025C28···H29nxiii3.21 (3)
N29···H32B2.6007C28···H28xiii3.3031
N29···H32C3.2663C28···H32Bvi3.5320
N29···H33A3.3292C28···H32Cvi3.5052
N29···H33B2.6812C28···H33Aiv3.5240
N29···H33C2.7158C28···H33Cxiii3.2005
C21···H233.2755C29···H12C3.0507
C21···H33A3.3374C29···H21nvi2.97 (3)
C21···H33B2.7385C29···H28xiii3.3757
C22···H21n2.60 (3)C29···H32Bvi3.4857
C22···H243.2822C29···H32Cvi2.8530
C24···H223.2747C30···H12C2.9201
C24···H262.6750C30···H9n3.41 (3)
C25···H233.2772C30···H32Cvi2.6341
C25···H273.2739C31···H21nvi3.22 (3)
C26···H242.6798C32···H2ii3.3457
C26···H283.2725C32···H1nii3.16 (3)
C28···H29n2.56 (3)C32···H21nvi3.31 (3)
C28···H263.2757C32···H22vi3.1551
C29···H273.2628C33···H12A3.4131
C29···H33B2.7948C33···H12Aii2.9801
C29···H33C3.4368C33···H27xiii3.3678
C30···H21n3.19 (3)C33···H28xiii3.2317
C30···H29n3.15 (3)H21n···H12Bvii3.1389
C30···H223.2913H21n···N21v3.43 (3)
C30···H243.3044H21n···N29v2.36 (3)
C30···H263.2958H21n···C28v3.56 (3)
C30···H283.2927H21n···C29v2.97 (3)
C30···H33B2.8207H21n···C31v3.22 (3)
C32···H21n2.54 (3)H21n···C32v3.31 (3)
C32···H29n2.55 (3)H21n···H29nv2.62 (4)
C32···H33A2.7154H21n···H28v3.5955
C32···H33B3.3464H21n···H32Av3.5842
C32···H33C2.6955H21n···H32Bv2.7055
C33···H21n2.72 (3)H21n···H33Avi3.3080
C33···H29n2.70 (3)H29n···C12xiii3.33 (3)
C33···H32A2.7227H29n···H12Bxiii2.6812
C33···H32B3.3512H29n···H12Cxiii3.1687
C33···H32C2.6755H29n···N21vi3.44 (3)
H21n···H222.4816H29n···C27xiii3.37 (3)
H21n···H32A3.4591H29n···C28xiii3.21 (3)
H21n···H32B2.7206H29n···H21nvi2.62 (4)
H21n···H32C2.4382H29n···H22vi3.1411
H21n···H33A2.5955H29n···H27xiii3.2349
H21n···H33B3.0340H29n···H28xiii2.9429
H21n···H33C3.5867H22···C12vii3.3848
H29n···H282.4525H22···C13vii3.5020
H29n···H32A2.4030H22···H12Bvii2.4947
H29n···H32B2.8080H22···H13Avii2.6455
H29n···H32C3.4507H22···H1nvii3.0137
H29n···H33A3.5809H22···N29v3.4504
H29n···H33B2.9771H22···C32v3.1551
H29n···H33C2.6048H22···H29nv3.1411
H22···H232.3458H22···H32Av2.8427
H23···H242.3130H22···H32Bv2.6236
H24···H262.5211H23···C3xii3.3451
H26···H272.3115H23···C6xi3.0985
H27···H282.3423H23···C7xi3.4722
H32A···H33A3.0419H23···C83.5491
H32A···H33B3.5989H23···C13vii3.3636
H32A···H33C2.5440H23···H3xii2.7873
H32B···H33A3.5913H23···H6xi2.8223
H32B···H33C3.5996H23···H7xi3.4557
H32C···H33A2.5146H23···H82.6159
H32C···H33B3.5739H23···H13Avii2.5254
H32C···H33C2.9414H23···H13Bvii3.4602
N1···H27iii3.2088H23···H9n3.2829
N1···H32Aii2.8729H23···H1nvii3.0707
N1···H32Cii3.2841H24···C6xi3.1342
N1···H33Cii3.3541H24···C7iv3.4416
N9···H26iii3.3501H24···C7xi3.3068
N9···H27iii2.8726H24···H2vii3.0432
C1···H4viii3.0226H24···H6xi2.4821
C1···H27iii3.4768H24···H7iv3.4063
C1···H32Aii3.1334H24···H7xi2.8182
C2···H4viii3.2340H24···H83.4350
C2···H6viii3.4343H24···H13C3.1356
C2···H32Aii3.0689H24···H9n2.9522
C3···H4viii3.3428H26···N9iv3.3501
C3···H7ix3.4852H26···C5iv3.0389
C3···H8ix3.4420H26···C6iv3.0731
C3···H13Aiii3.1595H26···C7iv2.9531
C3···H13Bx3.2186H26···C8iv2.7632
C3···H23ix3.3451H26···C9iv2.6822
C4···H4viii3.2736H26···C10iv2.8428
C4···H13Aiii3.1260H26···C133.5643
C4···H13Biii3.3632H26···H7iv3.5435
C4···H13Bx2.7866H26···H8iv3.2782
C4···H13Ciii3.1820H26···H12C3.2466
C5···H4viii3.0475H26···H13C2.6146
C5···H13Bx3.5298H27···N1iv3.2088
C5···H13Ciii3.1957H27···N9iv2.8726
C5···H26iii3.0389H27···C1iv3.4768
C6···H13Ciii3.4981H27···C9iv3.2013
C6···H23xi3.0985H27···C10iv3.4259
C6···H24xi3.1342H27···C11iv3.4733
C6···H26iii3.0731H27···H12Aiv3.0090
C7···H3xii3.3823H27···H12C3.4716
C7···H8xi3.2563H27···H9niv3.3681
C7···H23xi3.4722H27···C33xiii3.3678
C7···H24iii3.4416H27···H29nxiii3.2349
C7···H24xi3.3068H27···H32Axiii3.3116
C7···H26iii2.9531H27···H33Cxiii2.4122
C8···H3xii3.2750H28···C12xiii3.2555
C8···H7xi3.2821H28···H12Axiii2.9433
C8···H233.5491H28···H12Bxiii3.0861
C8···H26iii2.7632H28···H12Cxiii3.1900
C9···H26iii2.6822H28···N29xiii3.3733
C9···H27iii3.2013H28···C28xiii3.3031
C10···H4viii2.9010H28···C29xiii3.3757
C10···H26iii2.8428H28···C33xiii3.2317
C10···H27iii3.4259H28···H21nvi3.5955
C11···H27iii3.4733H28···H29nxiii2.9429
C12···H29nxiii3.33 (3)H28···H28xiii3.0967
C12···H22i3.3848H28···H33Aiv3.1040
C12···H28xiii3.2555H28···H33Bxiii3.0022
C12···H33Aii3.3470H28···H33Cxiii2.6672
C12···H33B3.1989H32A···N1ii2.8729
C12···H33Cii3.2500H32A···C1ii3.1334
C13···H4iv3.3865H32A···C2ii3.0689
C13···H4viii3.4499H32A···H2ii2.8014
C13···H22i3.5020H32A···H1nii2.7368
C13···H23i3.3636H32A···H21nvi3.5842
C13···H263.5643H32A···H22vi2.8427
H2···H6viii3.3533H32A···H27xiii3.3116
H2···H8ix3.4300H32B···H2ii3.4840
H2···C23i3.5084H32B···N21vi3.3261
H2···C24i3.0379H32B···C21vi3.5102
H2···C25i3.3639H32B···C22vi3.2046
H2···C32ii3.3457H32B···C28v3.5320
H2···H24i3.0432H32B···C29v3.4857
H2···H32Aii2.8014H32B···H21nvi2.7055
H2···H32Bii3.4840H32B···H22vi2.6236
H2···H32Cii3.2366H32B···H33Avi3.0150
H3···C7ix3.3823H32C···N1ii3.2841
H3···C8ix3.2750H32C···H2ii3.2366
H3···H7ix2.8157H32C···H1nii2.7066
H3···H8ix2.6041H32C···N21v3.1878
H3···H13Aiii3.2995H32C···N29v3.2210
H3···H13Bx3.2593H32C···C21v2.8885
H3···H23ix2.7873H32C···C25v3.1837
H4···C1x3.0226H32C···C28v3.5052
H4···C2x3.2340H32C···C29v2.8530
H4···C3x3.3428H32C···C30v2.6341
H4···C4x3.2736H33A···C12ii3.3470
H4···C5x3.0475H33A···H12Aii2.7227
H4···C10x2.9010H33A···H12Bii3.0943
H4···C13iii3.3865H33A···H1nii3.5589
H4···C13x3.4499H33A···N21v3.1063
H4···H13Aiii3.2321H33A···C28iii3.5240
H4···H13Biii3.0647H33A···H21nv3.3080
H4···H13Bx2.5235H33A···H28iii3.1040
H4···H13Ciii3.2978H33A···H32Bv3.0150
H6···C2x3.4343H33B···C123.1989
H6···H2x3.3533H33B···H12A2.5307
H6···H7xiv3.1679H33B···H12Aii3.4961
H6···C23xi3.3009H33B···H12C2.9969
H6···C24xi3.1308H33B···H28xiii3.0022
H6···H23xi2.8223H33B···H33Cii3.4670
H6···H24xi2.4821H33C···N1ii3.3541
H7···C3xii3.4852H33C···C12ii3.2500
H7···C8xi3.2821H33C···H12A3.5273
H7···H3xii2.8157H33C···H12Aii2.3971
H7···H6xiv3.1679H33C···H12Bii3.4433
H7···H8xi2.9778H33C···H1nii3.4702
H7···C24xi3.5757H33C···C27xiii3.0795
H7···H23xi3.4557H33C···C28xiii3.2005
H7···H24iii3.4063H33C···H27xiii2.4122
H7···H24xi2.8182H33C···H28xiii2.6672
H7···H26iii3.5435H33C···H33Bii3.4670
H8···C3xii3.4420
C1—N1—C11118.4 (3)C9—N9—H9n112.7 (18)
C9—N9—C11118.37 (19)C11—N9—H9n114.5 (17)
N1—C1—C2122.4 (3)C1—C2—H2120.147
N1—C1—C10117.7 (2)C3—C2—H2120.144
C2—C1—C10119.9 (2)C2—C3—H3119.198
C1—C2—C3119.7 (3)C4—C3—H3119.197
C2—C3—C4121.6 (3)C3—C4—H4119.883
C3—C4—C5120.2 (3)C5—C4—H4119.895
C4—C5—C6122.6 (3)C5—C6—H6119.925
C4—C5—C10118.7 (3)C7—C6—H6119.912
C6—C5—C10118.6 (3)C6—C7—H7119.315
C5—C6—C7120.2 (3)C8—C7—H7119.307
C6—C7—C8121.4 (3)C7—C8—H8119.937
C7—C8—C9120.1 (3)C9—C8—H8119.924
N9—C9—C8123.0 (2)C11—C12—H12A109.477
N9—C9—C10117.0 (3)C11—C12—H12B109.468
C8—C9—C10119.8 (2)C11—C12—H12C109.472
C1—C10—C5119.9 (2)H12A—C12—H12B109.474
C1—C10—C9120.3 (2)H12A—C12—H12C109.472
C5—C10—C9119.8 (3)H12B—C12—H12C109.463
N1—C11—N9106.33 (18)C11—C13—H13A109.472
N1—C11—C12107.6 (3)C11—C13—H13B109.473
N1—C11—C13111.97 (18)C11—C13—H13C109.473
N9—C11—C12108.72 (19)H13A—C13—H13B109.459
N9—C11—C13111.0 (3)H13A—C13—H13C109.477
C12—C11—C13111.01 (19)H13B—C13—H13C109.473
C21—N21—C31117.6 (2)C21—N21—H21n116.9 (16)
C29—N29—C31117.32 (19)C31—N21—H21n110.5 (18)
N21—C21—C22124.2 (2)C29—N29—H29n114.8 (16)
N21—C21—C30116.9 (3)C31—N29—H29n111.0 (16)
C22—C21—C30118.8 (2)C21—C22—H22119.693
C21—C22—C23120.6 (3)C23—C22—H22119.705
C22—C23—C24121.4 (3)C22—C23—H23119.309
C23—C24—C25119.9 (2)C24—C23—H23119.313
C24—C25—C26122.2 (2)C23—C24—H24120.020
C24—C25—C30119.0 (2)C25—C24—H24120.040
C26—C25—C30118.8 (3)C25—C26—H26119.885
C25—C26—C27120.2 (2)C27—C26—H26119.879
C26—C27—C28121.5 (3)C26—C27—H27119.268
C27—C28—C29120.0 (3)C28—C27—H27119.271
N29—C29—C28122.4 (3)C27—C28—H28120.016
N29—C29—C30117.9 (2)C29—C28—H28120.012
C28—C29—C30119.6 (2)C31—C32—H32A109.469
C21—C30—C25120.2 (3)C31—C32—H32B109.478
C21—C30—C29119.7 (2)C31—C32—H32C109.473
C25—C30—C29120.0 (2)H32A—C32—H32B109.470
N21—C31—N29105.38 (19)H32A—C32—H32C109.469
N21—C31—C32109.3 (2)H32B—C32—H32C109.468
N21—C31—C33110.55 (19)C31—C33—H33A109.483
N29—C31—C32108.00 (18)C31—C33—H33B109.470
N29—C31—C33111.9 (2)C31—C33—H33C109.475
C32—C31—C33111.4 (2)H33A—C33—H33B109.464
C1—N1—H1n114.0 (14)H33A—C33—H33C109.468
C11—N1—H1n114.2 (15)H33B—C33—H33C109.468
C1—N1—C11—N948.8 (3)C21—N21—C31—N2955.3 (3)
C1—N1—C11—C12165.13 (16)C21—N21—C31—C32171.11 (16)
C1—N1—C11—C1372.6 (3)C21—N21—C31—C3365.9 (3)
C11—N1—C1—C2156.31 (18)C31—N21—C21—C22150.43 (19)
C11—N1—C1—C1027.4 (3)C31—N21—C21—C3033.5 (3)
C9—N9—C11—N151.3 (3)C29—N29—C31—N2151.7 (3)
C9—N9—C11—C12166.88 (18)C29—N29—C31—C32168.5 (2)
C9—N9—C11—C1370.7 (3)C29—N29—C31—C3368.5 (3)
C11—N9—C9—C8153.29 (19)C31—N29—C29—C28157.1 (2)
C11—N9—C9—C1032.0 (3)C31—N29—C29—C3027.6 (3)
N1—C1—C2—C3175.13 (17)N21—C21—C22—C23174.14 (19)
N1—C1—C10—C5174.89 (17)N21—C21—C30—C25173.37 (18)
N1—C1—C10—C93.6 (3)N21—C21—C30—C294.1 (3)
C2—C1—C10—C51.5 (3)C22—C21—C30—C252.9 (3)
C2—C1—C10—C9179.97 (18)C22—C21—C30—C29179.64 (19)
C10—C1—C2—C31.1 (3)C30—C21—C22—C231.9 (4)
C1—C2—C3—C40.3 (4)C21—C22—C23—C240.3 (4)
C2—C3—C4—C51.2 (4)C22—C23—C24—C250.3 (4)
C3—C4—C5—C6179.83 (19)C23—C24—C25—C26178.4 (2)
C3—C4—C5—C100.8 (3)C23—C24—C25—C300.8 (4)
C4—C5—C6—C7179.12 (19)C24—C25—C26—C27178.6 (2)
C4—C5—C10—C10.6 (3)C24—C25—C30—C212.4 (4)
C4—C5—C10—C9179.05 (18)C24—C25—C30—C29179.82 (19)
C6—C5—C10—C1178.86 (18)C26—C25—C30—C21176.83 (19)
C6—C5—C10—C90.4 (3)C26—C25—C30—C290.6 (4)
C10—C5—C6—C71.5 (3)C30—C25—C26—C270.6 (4)
C5—C6—C7—C81.7 (4)C25—C26—C27—C281.7 (4)
C6—C7—C8—C90.1 (4)C26—C27—C28—C291.6 (4)
C7—C8—C9—N9172.64 (19)C27—C28—C29—N29174.8 (2)
C7—C8—C9—C101.9 (4)C27—C28—C29—C300.4 (4)
N9—C9—C10—C15.7 (3)N29—C29—C30—C211.3 (3)
N9—C9—C10—C5172.81 (17)N29—C29—C30—C25176.12 (18)
C8—C9—C10—C1179.45 (18)C28—C29—C30—C21176.72 (19)
C8—C9—C10—C52.1 (3)C28—C29—C30—C250.7 (4)
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+2, y+1, z+1; (iii) x, y+1, z; (iv) x, y1, z; (v) x+2, y+1/2, z+3/2; (vi) x+2, y1/2, z+3/2; (vii) x, y+1/2, z+1/2; (viii) x+1, y1/2, z+1/2; (ix) x, y+3/2, z1/2; (x) x+1, y+1/2, z+1/2; (xi) x+1, y+1, z+1; (xii) x, y+3/2, z+1/2; (xiii) x+2, y, z+1; (xiv) x+1, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the C21–C25/C30, C25–C30 and C5–C10 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N21—H21N···N29v0.88 (2)2.36 (2)3.229 (4)170 (2)
N1—H1N···Cg1i0.93 (3)2.93 (3)3.853 (3)170 (2)
N9—H9N···Cg10.88 (4)2.85 (2)3.703 (3)164 (2)
C12—H12C···Cg20.982.553.521 (3)172
C26—H26···Cg3iv0.952.533.456 (3)164
Symmetry codes: (i) x, y+1/2, z1/2; (iv) x, y1, z; (v) x+2, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC13H14N2
Mr198.27
Crystal system, space groupMonoclinic, P21/c
Temperature (K)93
a, b, c (Å)16.261 (10), 7.710 (4), 17.483 (10)
β (°) 106.131 (12)
V3)2105.6 (19)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.12 × 0.12 × 0.12
Data collection
DiffractometerRigaku Mercury70
diffractometer
Absorption correctionMulti-scan
(REQAB; Rigaku, 1998)
Tmin, Tmax0.706, 0.991
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
12841, 3743, 2356
Rint0.072
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.133, 0.96
No. of reflections3743
No. of parameters287
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.22, 0.24

Computer programs: CrystalClear-SM Expert (Rigaku, 2009), SIR2002 (Burla et al., 2003), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2010).

Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the C21–C25/C30, C25–C30 and C5–C10 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N21—H21N···N29i0.88 (2)2.36 (2)3.229 (4)170 (2)
N1—H1N···Cg1ii0.93 (3)2.93 (3)3.853 (3)170 (2)
N9—H9N···Cg10.88 (4)2.85 (2)3.703 (3)164 (2)
C12—H12C···Cg20.982.553.521 (3)172
C26—H26···Cg3iii0.952.533.456 (3)164
Symmetry codes: (i) x+2, y+1/2, z+3/2; (ii) x, y+1/2, z1/2; (iii) x, y1, z.
 

Acknowledgements

We are grateful to EPSRC for support.

References

First citationBurla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.  CrossRef IUCr Journals
First citationMartinez-Belmonte, M., Escudero-Adan, E. C., Benet-Buchholz, J., Haak, R. M. & Kleij, A. W. (2010). Eur. J. Inorg. Chem. pp. 4823–4831.
First citationRigaku (1998). REQAB. Rigaku Corporation, Tokyo, Japan.
First citationRigaku (2009). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.
First citationRigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
First citationSauer, M., Yeung, C., Lai, C.-C. & Chiu, S.-H. (2006). J. Org. Chem. 71, 775–788.  Web of Science CSD CrossRef PubMed CAS
First citationShaabani, A. & Maleki, A. (2008). Chem. Pharm. Bull. 56, 79–81.  Web of Science CrossRef PubMed CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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