In the title compound, C22H16N4, there are two crystallographically independent molecules, both of which are centrosymmetric and adopt a non-planar conformation.
Supporting information
CCDC reference: 277706
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.002 Å
- R factor = 0.044
- wR factor = 0.108
- Data-to-parameter ratio = 11.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem
0 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
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
Crystal data top
C22H16N4 | Z = 2 |
Mr = 336.39 | F(000) = 352 |
Triclinic, P1 | Dx = 1.335 Mg m−3 |
a = 7.6684 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.2831 (9) Å | Cell parameters from 2932 reflections |
c = 11.6172 (10) Å | θ = 2.8–25.0° |
α = 102.895 (2)° | µ = 0.08 mm−1 |
β = 102.286 (2)° | T = 150 K |
γ = 102.822 (2)° | Block, green–brown |
V = 836.89 (13) Å3 | 0.22 × 0.18 × 0.12 mm |
Data collection top
Bruker SMART APEX CCD diffractometer | 2357 reflections with I > 2σ(I) |
ω scans | Rint = 0.031 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 25.0°, θmin = 1.9° |
Tmin = 0.972, Tmax = 0.990 | h = −9→9 |
6742 measured reflections | k = −12→12 |
2957 independent reflections | l = −13→13 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Only H-atom displacement parameters refined |
R[F2 > 2σ(F2)] = 0.044 | w = 1/[σ2(Fo2) + (0.0491P)2 + 0.1827P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.108 | (Δ/σ)max = 0.001 |
S = 1.01 | Δρmax = 0.17 e Å−3 |
2957 reflections | Δρmin = −0.17 e Å−3 |
251 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 | x | y | z | Uiso*/Ueq | |
C1 | 0.1671 (3) | −0.04261 (19) | 0.35757 (16) | 0.0359 (5) | |
H1 | 0.1477 | −0.1296 | 0.2998 | 0.036 (5)* | |
C2 | 0.2478 (2) | −0.02822 (18) | 0.47912 (15) | 0.0318 (4) | |
H2 | 0.2847 | −0.1025 | 0.5037 | 0.039 (5)* | |
C3 | 0.2741 (2) | 0.09733 (17) | 0.56506 (15) | 0.0262 (4) | |
C4 | 0.2165 (2) | 0.20089 (18) | 0.52301 (16) | 0.0309 (4) | |
H4 | 0.2301 | 0.2878 | 0.579 | 0.035 (5)* | |
C5 | 0.1391 (2) | 0.17648 (19) | 0.39884 (16) | 0.0341 (4) | |
H5 | 0.1015 | 0.249 | 0.3715 | 0.040 (5)* | |
C6 | 0.3610 (2) | 0.12424 (18) | 0.69684 (15) | 0.0280 (4) | |
H6 | 0.373 | 0.2118 | 0.7512 | 0.031 (5)* | |
C7 | 0.5126 (2) | 0.07344 (18) | 0.86750 (14) | 0.0277 (4) | |
C8 | 0.6641 (2) | 0.18823 (19) | 0.92185 (16) | 0.0313 (4) | |
H8 | 0.7037 | 0.248 | 0.875 | 0.035 (5)* | |
C9 | 0.7608 (2) | 0.21794 (19) | 1.04607 (15) | 0.0312 (4) | |
H9 | 0.8661 | 0.2971 | 1.0822 | 0.030 (5)* | |
C10 | 0.7056 (2) | 0.13482 (18) | 1.11511 (15) | 0.0290 (4) | |
H10 | 0.7726 | 0.1562 | 1.199 | 0.023 (4)* | |
C11 | 0.5486 (2) | 0.01620 (17) | 1.06294 (14) | 0.0260 (4) | |
C12 | 0.7575 (3) | 0.5816 (2) | 1.01613 (16) | 0.0390 (5) | |
H12 | 0.7559 | 0.5015 | 1.0442 | 0.053 (6)* | |
C13 | 0.6407 (3) | 0.56464 (19) | 0.90322 (16) | 0.0357 (4) | |
H13 | 0.5599 | 0.4755 | 0.8561 | 0.048 (6)* | |
C14 | 0.6418 (2) | 0.67906 (18) | 0.85863 (15) | 0.0268 (4) | |
C15 | 0.7648 (2) | 0.80512 (18) | 0.93130 (15) | 0.0288 (4) | |
H15 | 0.7742 | 0.8857 | 0.9032 | 0.026 (5)* | |
C16 | 0.8742 (2) | 0.81266 (19) | 1.04537 (16) | 0.0317 (4) | |
H16 | 0.9545 | 0.9008 | 1.0953 | 0.033 (5)* | |
C17 | 0.5113 (2) | 0.67066 (18) | 0.74248 (15) | 0.0282 (4) | |
H17 | 0.5253 | 0.7487 | 0.7108 | 0.027 (5)* | |
C18 | 0.2578 (2) | 0.55852 (17) | 0.57273 (15) | 0.0264 (4) | |
C19 | 0.3207 (2) | 0.59687 (18) | 0.47999 (16) | 0.0310 (4) | |
H19 | 0.4507 | 0.6304 | 0.4908 | 0.035 (5)* | |
C20 | 0.1948 (2) | 0.58704 (19) | 0.36893 (16) | 0.0324 (4) | |
H20 | 0.2407 | 0.6149 | 0.3058 | 0.031 (5)* | |
C21 | 0.0077 (2) | 0.53810 (17) | 0.35062 (15) | 0.0292 (4) | |
H21 | −0.0757 | 0.5328 | 0.2753 | 0.023 (4)* | |
C22 | −0.0627 (2) | 0.49515 (17) | 0.44361 (14) | 0.0254 (4) | |
N1 | 0.1141 (2) | 0.05685 (16) | 0.31504 (13) | 0.0355 (4) | |
N2 | 0.4206 (2) | 0.03490 (15) | 0.74067 (12) | 0.0298 (4) | |
N3 | 0.8731 (2) | 0.70300 (16) | 1.08929 (13) | 0.0370 (4) | |
N4 | 0.37974 (19) | 0.56039 (14) | 0.68375 (12) | 0.0285 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0451 (11) | 0.0323 (10) | 0.0245 (10) | 0.0099 (9) | 0.0035 (8) | 0.0035 (8) |
C2 | 0.0371 (10) | 0.0303 (10) | 0.0267 (10) | 0.0111 (8) | 0.0043 (8) | 0.0084 (8) |
C3 | 0.0233 (9) | 0.0295 (9) | 0.0245 (9) | 0.0057 (7) | 0.0044 (7) | 0.0091 (7) |
C4 | 0.0326 (10) | 0.0275 (10) | 0.0279 (10) | 0.0060 (8) | 0.0030 (8) | 0.0060 (8) |
C5 | 0.0365 (10) | 0.0331 (10) | 0.0309 (10) | 0.0081 (8) | 0.0014 (8) | 0.0151 (9) |
C6 | 0.0313 (9) | 0.0279 (9) | 0.0221 (9) | 0.0082 (8) | 0.0050 (7) | 0.0043 (8) |
C7 | 0.0329 (10) | 0.0328 (10) | 0.0179 (8) | 0.0153 (8) | 0.0035 (7) | 0.0053 (7) |
C8 | 0.0351 (10) | 0.0325 (10) | 0.0271 (9) | 0.0120 (8) | 0.0063 (8) | 0.0097 (8) |
C9 | 0.0307 (10) | 0.0309 (10) | 0.0277 (10) | 0.0093 (8) | 0.0031 (8) | 0.0036 (8) |
C10 | 0.0307 (9) | 0.0337 (10) | 0.0192 (9) | 0.0145 (8) | −0.0009 (7) | 0.0028 (7) |
C11 | 0.0298 (9) | 0.0294 (9) | 0.0199 (8) | 0.0161 (8) | 0.0040 (7) | 0.0040 (7) |
C12 | 0.0458 (12) | 0.0345 (11) | 0.0330 (11) | 0.0108 (9) | 0.0013 (9) | 0.0121 (9) |
C13 | 0.0377 (10) | 0.0294 (10) | 0.0311 (10) | 0.0056 (8) | 0.0000 (8) | 0.0037 (8) |
C14 | 0.0254 (9) | 0.0304 (9) | 0.0236 (9) | 0.0101 (7) | 0.0062 (7) | 0.0041 (7) |
C15 | 0.0273 (9) | 0.0304 (10) | 0.0267 (9) | 0.0092 (8) | 0.0050 (7) | 0.0055 (8) |
C16 | 0.0275 (9) | 0.0322 (10) | 0.0278 (10) | 0.0054 (8) | 0.0018 (7) | 0.0024 (8) |
C17 | 0.0296 (9) | 0.0305 (10) | 0.0244 (9) | 0.0109 (8) | 0.0063 (7) | 0.0064 (8) |
C18 | 0.0310 (9) | 0.0233 (9) | 0.0227 (9) | 0.0118 (7) | 0.0016 (7) | 0.0037 (7) |
C19 | 0.0274 (10) | 0.0320 (10) | 0.0302 (10) | 0.0065 (8) | 0.0056 (8) | 0.0062 (8) |
C20 | 0.0374 (11) | 0.0365 (10) | 0.0251 (10) | 0.0112 (8) | 0.0100 (8) | 0.0104 (8) |
C21 | 0.0325 (10) | 0.0326 (10) | 0.0197 (9) | 0.0110 (8) | 0.0010 (7) | 0.0059 (7) |
C22 | 0.0298 (9) | 0.0209 (8) | 0.0219 (8) | 0.0089 (7) | 0.0018 (7) | 0.0025 (7) |
N1 | 0.0390 (9) | 0.0381 (9) | 0.0249 (8) | 0.0063 (7) | 0.0023 (7) | 0.0112 (7) |
N2 | 0.0342 (8) | 0.0338 (8) | 0.0209 (8) | 0.0112 (7) | 0.0046 (6) | 0.0081 (6) |
N3 | 0.0365 (9) | 0.0404 (9) | 0.0270 (8) | 0.0086 (7) | −0.0009 (7) | 0.0072 (7) |
N4 | 0.0274 (8) | 0.0296 (8) | 0.0231 (8) | 0.0090 (6) | −0.0001 (6) | 0.0029 (6) |
Geometric parameters (Å, º) top
C1—N1 | 1.334 (2) | C12—N3 | 1.335 (2) |
C1—C2 | 1.376 (2) | C12—C13 | 1.372 (2) |
C1—H1 | 0.95 | C12—H12 | 0.95 |
C2—C3 | 1.388 (2) | C13—C14 | 1.387 (2) |
C2—H2 | 0.95 | C13—H13 | 0.95 |
C3—C4 | 1.385 (2) | C14—C15 | 1.383 (2) |
C3—C6 | 1.469 (2) | C14—C17 | 1.471 (2) |
C4—C5 | 1.380 (2) | C15—C16 | 1.385 (2) |
C4—H4 | 0.95 | C15—H15 | 0.95 |
C5—N1 | 1.334 (2) | C16—N3 | 1.337 (2) |
C5—H5 | 0.95 | C16—H16 | 0.95 |
C6—N2 | 1.268 (2) | C17—N4 | 1.274 (2) |
C6—H6 | 0.95 | C17—H17 | 0.95 |
C7—C8 | 1.374 (2) | C18—C19 | 1.370 (2) |
C7—N2 | 1.414 (2) | C18—N4 | 1.416 (2) |
C7—C11i | 1.423 (2) | C18—C22ii | 1.430 (2) |
C8—C9 | 1.405 (2) | C19—C20 | 1.405 (2) |
C8—H8 | 0.95 | C19—H19 | 0.95 |
C9—C10 | 1.358 (2) | C20—C21 | 1.364 (2) |
C9—H9 | 0.95 | C20—H20 | 0.95 |
C10—C11 | 1.419 (2) | C21—C22 | 1.417 (2) |
C10—H10 | 0.95 | C21—H21 | 0.95 |
C11—C11i | 1.419 (3) | C22—C22ii | 1.419 (3) |
C11—C7i | 1.423 (2) | C22—C18ii | 1.430 (2) |
| | | |
N1—C1—C2 | 124.66 (17) | C13—C12—H12 | 117.8 |
N1—C1—H1 | 117.7 | C12—C13—C14 | 119.23 (17) |
C2—C1—H1 | 117.7 | C12—C13—H13 | 120.4 |
C1—C2—C3 | 118.44 (17) | C14—C13—H13 | 120.4 |
C1—C2—H2 | 120.8 | C15—C14—C13 | 117.24 (15) |
C3—C2—H2 | 120.8 | C15—C14—C17 | 120.48 (16) |
C4—C3—C2 | 117.75 (15) | C13—C14—C17 | 122.19 (16) |
C4—C3—C6 | 119.39 (15) | C14—C15—C16 | 119.34 (17) |
C2—C3—C6 | 122.85 (15) | C14—C15—H15 | 120.3 |
C5—C4—C3 | 119.25 (16) | C16—C15—H15 | 120.3 |
C5—C4—H4 | 120.4 | N3—C16—C15 | 123.74 (17) |
C3—C4—H4 | 120.4 | N3—C16—H16 | 118.1 |
N1—C5—C4 | 123.72 (17) | C15—C16—H16 | 118.1 |
N1—C5—H5 | 118.1 | N4—C17—C14 | 121.07 (16) |
C4—C5—H5 | 118.1 | N4—C17—H17 | 119.5 |
N2—C6—C3 | 122.42 (15) | C14—C17—H17 | 119.5 |
N2—C6—H6 | 118.8 | C19—C18—N4 | 122.49 (15) |
C3—C6—H6 | 118.8 | C19—C18—C22ii | 120.17 (15) |
C8—C7—N2 | 121.94 (15) | N4—C18—C22ii | 117.19 (15) |
C8—C7—C11i | 120.14 (15) | C18—C19—C20 | 120.62 (16) |
N2—C7—C11i | 117.78 (15) | C18—C19—H19 | 119.7 |
C7—C8—C9 | 120.55 (17) | C20—C19—H19 | 119.7 |
C7—C8—H8 | 119.7 | C21—C20—C19 | 120.86 (17) |
C9—C8—H8 | 119.7 | C21—C20—H20 | 119.6 |
C10—C9—C8 | 120.77 (17) | C19—C20—H20 | 119.6 |
C10—C9—H9 | 119.6 | C20—C21—C22 | 120.19 (15) |
C8—C9—H9 | 119.6 | C20—C21—H21 | 119.9 |
C9—C10—C11 | 120.48 (15) | C22—C21—H21 | 119.9 |
C9—C10—H10 | 119.8 | C21—C22—C22ii | 119.60 (19) |
C11—C10—H10 | 119.8 | C21—C22—C18ii | 121.86 (14) |
C10—C11—C11i | 119.3 (2) | C22ii—C22—C18ii | 118.54 (19) |
C10—C11—C7i | 121.94 (14) | C5—N1—C1 | 116.15 (15) |
C11i—C11—C7i | 118.7 (2) | C6—N2—C7 | 118.28 (14) |
N3—C12—C13 | 124.49 (18) | C12—N3—C16 | 115.92 (15) |
N3—C12—H12 | 117.8 | C17—N4—C18 | 118.59 (15) |
| | | |
N1—C1—C2—C3 | 1.1 (3) | C14—C15—C16—N3 | 2.3 (3) |
C1—C2—C3—C4 | 0.2 (3) | C15—C14—C17—N4 | −169.68 (16) |
C1—C2—C3—C6 | −179.22 (16) | C13—C14—C17—N4 | 6.8 (3) |
C2—C3—C4—C5 | −1.1 (3) | N4—C18—C19—C20 | 176.89 (16) |
C6—C3—C4—C5 | 178.42 (16) | C22ii—C18—C19—C20 | 1.4 (3) |
C3—C4—C5—N1 | 0.6 (3) | C18—C19—C20—C21 | −0.6 (3) |
C4—C3—C6—N2 | −178.32 (16) | C19—C20—C21—C22 | −0.5 (3) |
C2—C3—C6—N2 | 1.1 (3) | C20—C21—C22—C22ii | 0.7 (3) |
N2—C7—C8—C9 | −175.25 (15) | C20—C21—C22—C18ii | −179.13 (16) |
C11i—C7—C8—C9 | 0.4 (3) | C4—C5—N1—C1 | 0.6 (3) |
C7—C8—C9—C10 | −0.7 (3) | C2—C1—N1—C5 | −1.6 (3) |
C8—C9—C10—C11 | −0.1 (3) | C3—C6—N2—C7 | 176.10 (15) |
C9—C10—C11—C11i | 1.1 (3) | C8—C7—N2—C6 | −55.2 (2) |
C9—C10—C11—C7i | 179.73 (16) | C11i—C7—N2—C6 | 129.06 (17) |
N3—C12—C13—C14 | 1.1 (3) | C13—C12—N3—C16 | −1.4 (3) |
C12—C13—C14—C15 | 0.9 (3) | C15—C16—N3—C12 | −0.3 (3) |
C12—C13—C14—C17 | −175.59 (17) | C14—C17—N4—C18 | 179.71 (15) |
C13—C14—C15—C16 | −2.5 (2) | C19—C18—N4—C17 | 51.1 (2) |
C17—C14—C15—C16 | 174.09 (15) | C22ii—C18—N4—C17 | −133.30 (16) |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x, −y+1, −z+1. |