Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805017940/is6089sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805017940/is6089Isup2.hkl |
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.
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 |
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 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 |
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. |
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) |
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) |
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. |
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