The title compound, C
13H
11N
3, contains coplanar fused heterocyclic rings. The dihedral angle between the imidazole ring and the attached benzene ring is 26.96 (7)°. Weak C—H
N interactions stabilize the crystal structure.
Supporting information
CCDC reference: 643096
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.046
- wR factor = 0.128
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.751 1.000
Tmin(prime) and Tmax expected: 0.958 0.975
RR(prime) = 0.764
Please check that your absorption correction is appropriate.
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.67 Sigma
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.76
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98
PLAT245_ALERT_2_C U(iso) H16D Smaller than U(eq) C16 by ... 0.01 AngSq
PLAT245_ALERT_2_C U(iso) H16E Smaller than U(eq) C16 by ... 0.03 AngSq
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12 .. N5 .. 2.72 Ang.
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
3 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXTL.
3-
p-Tolylimidazo[1,2-
b]pyridazine
top
Crystal data top
C13H11N3 | F(000) = 440 |
Mr = 209.25 | Dx = 1.296 Mg m−3 |
Monoclinic, P21/n | Melting point: 374.5 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 5.6240 (6) Å | Cell parameters from 2134 reflections |
b = 10.6353 (12) Å | θ = 4.6–55.0° |
c = 17.975 (2) Å | µ = 0.08 mm−1 |
β = 94.285 (2)° | T = 293 K |
V = 1072.1 (2) Å3 | Block, yellow |
Z = 4 | 0.52 × 0.50 × 0.32 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2319 independent reflections |
Radiation source: fine-focus sealed tube | 1769 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.073 |
φ and ω scans | θmax = 27.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→6 |
Tmin = 0.751, Tmax = 1.000 | k = −13→13 |
6153 measured reflections | l = −22→21 |
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)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.129 | w = 1/[σ2(Fo2) + (0.0582P)2 + 0.0061P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
2319 reflections | Δρmax = 0.17 e Å−3 |
150 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.008 (3) |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
N1 | 0.2300 (2) | 0.50241 (13) | 0.91387 (7) | 0.0615 (4) | |
N4 | 0.26061 (18) | 0.68524 (10) | 0.85425 (6) | 0.0408 (3) | |
N5 | 0.2195 (2) | 0.80698 (12) | 0.83546 (7) | 0.0525 (4) | |
C2 | 0.3973 (3) | 0.49595 (15) | 0.86348 (9) | 0.0574 (4) | |
H2 | 0.4860 | 0.4239 | 0.8557 | 0.069* | |
C3 | 0.4232 (2) | 0.60633 (13) | 0.82500 (7) | 0.0431 (3) | |
C6 | 0.0521 (3) | 0.85985 (16) | 0.87093 (9) | 0.0613 (5) | |
H6 | 0.0182 | 0.9438 | 0.8602 | 0.074* | |
C7 | −0.0820 (3) | 0.80069 (17) | 0.92408 (9) | 0.0627 (5) | |
H7 | −0.2024 | 0.8443 | 0.9458 | 0.075* | |
C8 | −0.0338 (3) | 0.67988 (16) | 0.94328 (8) | 0.0563 (4) | |
H8 | −0.1177 | 0.6391 | 0.9789 | 0.068* | |
C9 | 0.1464 (2) | 0.61820 (14) | 0.90779 (7) | 0.0466 (4) | |
C10 | 0.5717 (2) | 0.63316 (13) | 0.76354 (7) | 0.0405 (3) | |
C11 | 0.7754 (2) | 0.56041 (14) | 0.75597 (8) | 0.0501 (4) | |
H11 | 0.8232 | 0.5028 | 0.7930 | 0.060* | |
C12 | 0.9060 (2) | 0.57239 (15) | 0.69497 (8) | 0.0527 (4) | |
H12 | 1.0407 | 0.5226 | 0.6916 | 0.063* | |
C13 | 0.8422 (2) | 0.65682 (15) | 0.63826 (8) | 0.0476 (4) | |
C14 | 0.6441 (3) | 0.73155 (14) | 0.64683 (8) | 0.0491 (4) | |
H14 | 0.5999 | 0.7908 | 0.6104 | 0.059* | |
C15 | 0.5106 (2) | 0.72056 (14) | 0.70778 (8) | 0.0459 (4) | |
H15 | 0.3785 | 0.7721 | 0.7117 | 0.055* | |
C16 | 0.9808 (3) | 0.66596 (19) | 0.57012 (9) | 0.0649 (5) | |
H16A | 0.9108 | 0.7292 | 0.5372 | 0.097* | 0.58 (3) |
H16B | 0.9771 | 0.5863 | 0.5449 | 0.097* | 0.58 (3) |
H16C | 1.1430 | 0.6882 | 0.5847 | 0.097* | 0.58 (3) |
H16D | 1.1098 | 0.6066 | 0.5740 | 0.053 (12)* | 0.42 (3) |
H16F | 1.0435 | 0.7495 | 0.5663 | 0.075 (15)* | 0.42 (3) |
H16E | 0.8776 | 0.6476 | 0.5265 | 0.040 (10)* | 0.42 (3) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0739 (9) | 0.0560 (9) | 0.0570 (8) | −0.0044 (7) | 0.0205 (7) | 0.0141 (6) |
N4 | 0.0421 (6) | 0.0439 (7) | 0.0371 (6) | −0.0044 (5) | 0.0072 (5) | 0.0039 (5) |
N5 | 0.0566 (8) | 0.0490 (8) | 0.0541 (7) | 0.0065 (6) | 0.0191 (6) | 0.0108 (6) |
C2 | 0.0657 (10) | 0.0478 (9) | 0.0602 (9) | 0.0019 (7) | 0.0151 (8) | 0.0085 (7) |
C3 | 0.0425 (7) | 0.0447 (8) | 0.0425 (7) | −0.0026 (6) | 0.0053 (6) | 0.0026 (6) |
C6 | 0.0656 (10) | 0.0596 (10) | 0.0616 (10) | 0.0154 (8) | 0.0241 (8) | 0.0104 (8) |
C7 | 0.0605 (10) | 0.0767 (12) | 0.0540 (9) | 0.0084 (8) | 0.0243 (8) | 0.0053 (8) |
C8 | 0.0564 (9) | 0.0738 (11) | 0.0404 (8) | −0.0098 (8) | 0.0158 (7) | 0.0045 (7) |
C9 | 0.0516 (8) | 0.0516 (9) | 0.0374 (7) | −0.0095 (6) | 0.0082 (6) | 0.0059 (6) |
C10 | 0.0382 (7) | 0.0425 (8) | 0.0410 (7) | −0.0041 (6) | 0.0044 (5) | −0.0018 (6) |
C11 | 0.0458 (8) | 0.0518 (9) | 0.0527 (9) | 0.0030 (6) | 0.0028 (7) | 0.0028 (7) |
C12 | 0.0387 (7) | 0.0602 (10) | 0.0598 (9) | 0.0030 (6) | 0.0081 (7) | −0.0079 (8) |
C13 | 0.0416 (8) | 0.0559 (9) | 0.0463 (8) | −0.0095 (6) | 0.0107 (6) | −0.0105 (7) |
C14 | 0.0493 (8) | 0.0568 (9) | 0.0419 (8) | −0.0020 (7) | 0.0092 (6) | 0.0044 (6) |
C15 | 0.0421 (7) | 0.0503 (9) | 0.0462 (8) | 0.0035 (6) | 0.0087 (6) | 0.0024 (6) |
C16 | 0.0562 (10) | 0.0851 (13) | 0.0557 (10) | −0.0063 (9) | 0.0185 (8) | −0.0145 (9) |
Geometric parameters (Å, º) top
N1—C9 | 1.320 (2) | C10—C11 | 1.3971 (19) |
N1—C2 | 1.3559 (19) | C11—C12 | 1.3705 (19) |
N4—N5 | 1.3536 (16) | C11—H11 | 0.9300 |
N4—C3 | 1.3745 (17) | C12—C13 | 1.385 (2) |
N4—C9 | 1.3927 (16) | C12—H12 | 0.9300 |
N5—C6 | 1.3034 (18) | C13—C14 | 1.387 (2) |
C2—C3 | 1.3757 (19) | C13—C16 | 1.503 (2) |
C2—H2 | 0.9300 | C14—C15 | 1.378 (2) |
C3—C10 | 1.4619 (18) | C14—H14 | 0.9300 |
C6—C7 | 1.409 (2) | C15—H15 | 0.9300 |
C6—H6 | 0.9300 | C16—H16A | 0.9600 |
C7—C8 | 1.353 (2) | C16—H16B | 0.9600 |
C7—H7 | 0.9300 | C16—H16C | 0.9600 |
C8—C9 | 1.400 (2) | C16—H16D | 0.9600 |
C8—H8 | 0.9300 | C16—H16F | 0.9600 |
C10—C15 | 1.3911 (19) | C16—H16E | 0.9600 |
| | | |
C9—N1—C2 | 104.64 (12) | C12—C11—H11 | 119.4 |
N5—N4—C3 | 126.50 (11) | C10—C11—H11 | 119.4 |
N5—N4—C9 | 125.66 (11) | C11—C12—C13 | 121.60 (13) |
C3—N4—C9 | 107.84 (11) | C11—C12—H12 | 119.2 |
C6—N5—N4 | 114.01 (12) | C13—C12—H12 | 119.2 |
N1—C2—C3 | 113.42 (14) | C12—C13—C14 | 117.12 (13) |
N1—C2—H2 | 123.3 | C12—C13—C16 | 121.32 (14) |
C3—C2—H2 | 123.3 | C14—C13—C16 | 121.56 (15) |
N4—C3—C2 | 103.31 (12) | C15—C14—C13 | 121.97 (14) |
N4—C3—C10 | 127.15 (12) | C15—C14—H14 | 119.0 |
C2—C3—C10 | 129.37 (13) | C13—C14—H14 | 119.0 |
N5—C6—C7 | 125.58 (15) | C14—C15—C10 | 120.62 (13) |
N5—C6—H6 | 117.2 | C14—C15—H15 | 119.7 |
C7—C6—H6 | 117.2 | C10—C15—H15 | 119.7 |
C8—C7—C6 | 119.35 (14) | C13—C16—H16A | 109.5 |
C8—C7—H7 | 120.3 | C13—C16—H16B | 109.5 |
C6—C7—H7 | 120.3 | H16A—C16—H16B | 109.5 |
C7—C8—C9 | 117.82 (13) | C13—C16—H16C | 109.5 |
C7—C8—H8 | 121.1 | H16A—C16—H16C | 109.5 |
C9—C8—H8 | 121.1 | H16B—C16—H16C | 109.5 |
N1—C9—N4 | 110.79 (12) | C13—C16—H16D | 109.5 |
N1—C9—C8 | 131.67 (14) | C13—C16—H16F | 109.5 |
N4—C9—C8 | 117.51 (14) | H16D—C16—H16F | 109.5 |
C15—C10—C11 | 117.40 (12) | C13—C16—H16E | 109.5 |
C15—C10—C3 | 123.40 (12) | H16D—C16—H16E | 109.5 |
C11—C10—C3 | 118.96 (12) | H16F—C16—H16E | 109.5 |
C12—C11—C10 | 121.24 (13) | | |
| | | |
C3—N4—N5—C6 | 178.88 (14) | C3—N4—C9—C8 | −177.90 (12) |
C9—N4—N5—C6 | −2.0 (2) | C7—C8—C9—N1 | −179.00 (17) |
C9—N1—C2—C3 | 0.12 (19) | C7—C8—C9—N4 | −1.0 (2) |
N5—N4—C3—C2 | 178.88 (13) | N4—C3—C10—C15 | −25.5 (2) |
C9—N4—C3—C2 | −0.35 (15) | C2—C3—C10—C15 | 149.04 (16) |
N5—N4—C3—C10 | −5.4 (2) | N4—C3—C10—C11 | 160.33 (13) |
C9—N4—C3—C10 | 175.32 (12) | C2—C3—C10—C11 | −25.1 (2) |
N1—C2—C3—N4 | 0.15 (17) | C15—C10—C11—C12 | −1.7 (2) |
N1—C2—C3—C10 | −175.39 (14) | C3—C10—C11—C12 | 172.79 (13) |
N4—N5—C6—C7 | −0.5 (2) | C10—C11—C12—C13 | 0.0 (2) |
N5—C6—C7—C8 | 2.2 (3) | C11—C12—C13—C14 | 1.8 (2) |
C6—C7—C8—C9 | −1.2 (2) | C11—C12—C13—C16 | −177.62 (14) |
C2—N1—C9—N4 | −0.35 (17) | C12—C13—C14—C15 | −1.9 (2) |
C2—N1—C9—C8 | 177.71 (16) | C16—C13—C14—C15 | 177.53 (14) |
N5—N4—C9—N1 | −178.78 (13) | C13—C14—C15—C10 | 0.2 (2) |
C3—N4—C9—N1 | 0.46 (16) | C11—C10—C15—C14 | 1.6 (2) |
N5—N4—C9—C8 | 2.9 (2) | C3—C10—C15—C14 | −172.61 (13) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···N1i | 0.93 | 2.56 | 3.4630 (19) | 163 |
C12—H12···N5ii | 0.93 | 2.72 | 3.5882 (19) | 155 |
Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x+3/2, y−1/2, −z+3/2. |