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The supramolecular assembly of halogenated and hydroxyl hydrazones derived from two well known pharmaceuticals, isoniazid (Is
X, where
X = I, Br, OH) and hydralazine (Hy
X, where
X = I, Br, OH), was studied by X-ray crystallography and theoretical methods. Crystal packing of IsI and HyI shows weak I
N and I
π halogen bonds, whereas the hydrogen bonds are dominant in the brominated scaffolds IsBr and HyBr. Although the calculated I
N interaction strength appears almost three times weaker than the O—H
N contacts in the isoniazid-based hydrazones, the higher directionality of the halogen bonds induces a linear and planar architecture of self-complementary tectons, observed only with the help of a bridging water molecule in the case of IsOH. Finally, the X-ray structure of HyOH is characterized by an unexpected linear arrangement of clathrated dichloromethane molecules bound through type I and II halogen bonds. This rare phenomenon, observed in less than ten structures, was studied by coupled cluster-based energy decomposition.
Supporting information
CCDC references: 1820529; 1820530; 1820531; 1820532; 1820533
For all structures, data collection: MAR; cell refinement: CrysAlis PRO, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01); data reduction: CrysAlis PRO, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01); program(s) used to solve structure: SHELXT (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: 'Mercury (Macrae et al., 2008), PLATON (Spek, 2009)'.
Crystal data top
C13H10IN3O | Z = 4 |
Mr = 351.14 | F(000) = 680 |
Triclinic, P1 | Dx = 1.852 Mg m−3 |
a = 10.0223 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.1984 (3) Å | Cell parameters from 9164 reflections |
c = 12.4505 (10) Å | θ = 3.2–25.8° |
α = 109.836 (6)° | µ = 2.53 mm−1 |
β = 101.250 (7)° | T = 297 K |
γ = 97.494 (6)° | Block, colourless |
V = 1259.58 (17) Å3 | 0.50 × 0.20 × 0.10 mm |
Data collection top
MAR345 image plate diffractometer | 4823 independent reflections |
Radiation source: Rigaku UltraX 18 rotating anode | 4533 reflections with I > 2σ(I) |
Xenocs Fox3D mirror monochromator | Rint = 0.038 |
'110 images, ΔΦ 2.5° '
' 55 images, ΔΦ 2.5° ' scans | θmax = 25.9°, θmin = 3.0° |
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | h = −12→12 |
Tmin = 0.506, Tmax = 1.000 | k = −13→13 |
18494 measured reflections | l = −15→15 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.029 | H-atom parameters constrained |
wR(F2) = 0.080 | w = 1/[σ2(Fo2) + (0.052P)2 + 0.5361P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.002 |
4823 reflections | Δρmax = 0.61 e Å−3 |
325 parameters | Δρmin = −0.49 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.75073 (2) | 1.06523 (2) | 1.05620 (2) | 0.05001 (9) | |
C2 | 0.7127 (3) | 0.8800 (2) | 0.9233 (2) | 0.0422 (6) | |
C3 | 0.8014 (3) | 0.8525 (3) | 0.8506 (3) | 0.0463 (6) | |
H3 | 0.8794 | 0.9149 | 0.8622 | 0.056* | |
C4 | 0.7743 (3) | 0.7321 (3) | 0.7605 (3) | 0.0461 (6) | |
H4 | 0.8343 | 0.7140 | 0.7115 | 0.055* | |
C5 | 0.6577 (3) | 0.6373 (2) | 0.7421 (2) | 0.0404 (5) | |
C6 | 0.5709 (3) | 0.6652 (3) | 0.8180 (2) | 0.0431 (6) | |
H6 | 0.4945 | 0.6022 | 0.8084 | 0.052* | |
C7 | 0.5973 (3) | 0.7855 (3) | 0.9074 (3) | 0.0452 (6) | |
H7 | 0.5382 | 0.8037 | 0.9571 | 0.054* | |
C8 | 0.6343 (3) | 0.5109 (3) | 0.6467 (2) | 0.0427 (6) | |
H8 | 0.7038 | 0.4920 | 0.6079 | 0.051* | |
N9 | 0.5218 (2) | 0.4254 (2) | 0.6146 (2) | 0.0429 (5) | |
N10 | 0.5209 (2) | 0.3089 (2) | 0.5288 (2) | 0.0409 (5) | |
H10 | 0.5944 | 0.2967 | 0.5043 | 0.049* | |
C11 | 0.4040 (2) | 0.2133 (2) | 0.4826 (2) | 0.0381 (5) | |
O12 | 0.29362 (18) | 0.22760 (19) | 0.50696 (18) | 0.0528 (5) | |
C13 | 0.4186 (3) | 0.0880 (3) | 0.3979 (2) | 0.0370 (5) | |
C14 | 0.5060 (3) | 0.0774 (3) | 0.3231 (2) | 0.0430 (6) | |
H14 | 0.5636 | 0.1510 | 0.3257 | 0.052* | |
C15 | 0.5064 (3) | −0.0444 (3) | 0.2443 (3) | 0.0512 (7) | |
H15 | 0.5655 | −0.0501 | 0.1946 | 0.061* | |
N16 | 0.4267 (3) | −0.1539 (2) | 0.2359 (2) | 0.0530 (6) | |
C17 | 0.3456 (3) | −0.1429 (3) | 0.3096 (3) | 0.0485 (6) | |
H17 | 0.2909 | −0.2185 | 0.3061 | 0.058* | |
C18 | 0.3372 (3) | −0.0261 (3) | 0.3913 (2) | 0.0422 (5) | |
H18 | 0.2783 | −0.0239 | 0.4408 | 0.051* | |
I21 | 0.30846 (2) | 0.57424 (2) | 1.04111 (2) | 0.05183 (9) | |
C22 | 0.2142 (3) | 0.3858 (2) | 0.9169 (2) | 0.0424 (6) | |
C23 | 0.0896 (3) | 0.3231 (3) | 0.9238 (3) | 0.0531 (7) | |
H23 | 0.0476 | 0.3640 | 0.9825 | 0.064* | |
C24 | 0.0278 (3) | 0.1982 (3) | 0.8420 (3) | 0.0502 (6) | |
H24 | −0.0562 | 0.1558 | 0.8461 | 0.060* | |
C25 | 0.0903 (3) | 0.1362 (2) | 0.7542 (2) | 0.0399 (5) | |
C26 | 0.2140 (3) | 0.2023 (3) | 0.7478 (2) | 0.0445 (6) | |
H26 | 0.2557 | 0.1625 | 0.6884 | 0.053* | |
C27 | 0.2759 (3) | 0.3264 (3) | 0.8282 (3) | 0.0474 (6) | |
H27 | 0.3585 | 0.3698 | 0.8229 | 0.057* | |
C28 | 0.0245 (3) | 0.0038 (3) | 0.6719 (2) | 0.0424 (6) | |
H28 | −0.0653 | −0.0317 | 0.6706 | 0.051* | |
N29 | 0.0874 (2) | −0.0646 (2) | 0.6017 (2) | 0.0421 (5) | |
N30 | 0.0096 (2) | −0.1865 (2) | 0.5276 (2) | 0.0415 (5) | |
H30 | −0.0781 | −0.2057 | 0.5219 | 0.050* | |
C31 | 0.0719 (2) | −0.2751 (2) | 0.4644 (2) | 0.0370 (5) | |
O32 | 0.19617 (19) | −0.25530 (18) | 0.46947 (19) | 0.0502 (4) | |
C33 | −0.0217 (3) | −0.4033 (2) | 0.3864 (2) | 0.0369 (5) | |
C34 | −0.1380 (3) | −0.4579 (3) | 0.4125 (2) | 0.0437 (6) | |
H34 | −0.1664 | −0.4118 | 0.4785 | 0.052* | |
C35 | −0.2109 (3) | −0.5820 (3) | 0.3387 (3) | 0.0508 (6) | |
H35 | −0.2879 | −0.6176 | 0.3576 | 0.061* | |
N36 | −0.1774 (3) | −0.6537 (2) | 0.2421 (2) | 0.0559 (6) | |
C37 | −0.0679 (3) | −0.5995 (3) | 0.2164 (3) | 0.0551 (7) | |
H37 | −0.0443 | −0.6468 | 0.1481 | 0.066* | |
C38 | 0.0128 (3) | −0.4768 (3) | 0.2852 (2) | 0.0463 (6) | |
H38 | 0.0894 | −0.4441 | 0.2639 | 0.056* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.05518 (13) | 0.03297 (12) | 0.04734 (13) | 0.00340 (8) | 0.01112 (9) | 0.00046 (8) |
C2 | 0.0450 (14) | 0.0303 (12) | 0.0396 (13) | 0.0048 (10) | 0.0042 (11) | 0.0035 (10) |
C3 | 0.0425 (13) | 0.0338 (13) | 0.0534 (16) | −0.0005 (10) | 0.0108 (12) | 0.0090 (11) |
C4 | 0.0453 (14) | 0.0381 (13) | 0.0477 (15) | 0.0049 (11) | 0.0147 (11) | 0.0072 (11) |
C5 | 0.0408 (13) | 0.0311 (12) | 0.0405 (14) | 0.0044 (10) | 0.0058 (10) | 0.0063 (11) |
C6 | 0.0394 (13) | 0.0342 (13) | 0.0463 (15) | 0.0013 (10) | 0.0097 (11) | 0.0066 (11) |
C7 | 0.0444 (14) | 0.0375 (13) | 0.0466 (15) | 0.0068 (11) | 0.0162 (11) | 0.0054 (11) |
C8 | 0.0431 (13) | 0.0344 (13) | 0.0430 (14) | 0.0057 (10) | 0.0114 (11) | 0.0059 (11) |
N9 | 0.0409 (11) | 0.0315 (11) | 0.0432 (12) | 0.0057 (9) | 0.0089 (9) | −0.0002 (9) |
N10 | 0.0348 (11) | 0.0326 (11) | 0.0451 (11) | 0.0063 (9) | 0.0115 (9) | 0.0016 (9) |
C11 | 0.0332 (11) | 0.0343 (12) | 0.0402 (13) | 0.0049 (9) | 0.0084 (10) | 0.0073 (10) |
O12 | 0.0364 (9) | 0.0470 (10) | 0.0622 (12) | 0.0067 (8) | 0.0183 (9) | 0.0023 (9) |
C13 | 0.0318 (11) | 0.0329 (13) | 0.0380 (13) | 0.0046 (9) | 0.0033 (9) | 0.0071 (10) |
C14 | 0.0462 (14) | 0.0352 (13) | 0.0427 (14) | 0.0024 (10) | 0.0159 (11) | 0.0082 (11) |
C15 | 0.0587 (16) | 0.0409 (15) | 0.0481 (16) | 0.0066 (12) | 0.0221 (13) | 0.0061 (12) |
N16 | 0.0642 (15) | 0.0326 (11) | 0.0477 (13) | 0.0052 (11) | 0.0149 (12) | −0.0012 (10) |
C17 | 0.0506 (15) | 0.0341 (13) | 0.0506 (16) | −0.0011 (11) | 0.0083 (12) | 0.0097 (12) |
C18 | 0.0394 (12) | 0.0385 (13) | 0.0432 (14) | 0.0024 (10) | 0.0120 (10) | 0.0099 (11) |
I21 | 0.05536 (13) | 0.03383 (12) | 0.04794 (13) | 0.00371 (8) | 0.00365 (9) | 0.00012 (8) |
C22 | 0.0434 (13) | 0.0329 (13) | 0.0386 (13) | 0.0052 (10) | 0.0038 (10) | 0.0030 (10) |
C23 | 0.0574 (17) | 0.0446 (15) | 0.0488 (16) | 0.0067 (13) | 0.0230 (13) | 0.0035 (12) |
C24 | 0.0482 (15) | 0.0400 (14) | 0.0519 (16) | −0.0013 (11) | 0.0200 (12) | 0.0041 (12) |
C25 | 0.0389 (12) | 0.0338 (13) | 0.0384 (13) | 0.0052 (10) | 0.0071 (10) | 0.0053 (10) |
C26 | 0.0414 (13) | 0.0383 (14) | 0.0433 (14) | 0.0050 (11) | 0.0127 (11) | 0.0026 (11) |
C27 | 0.0404 (13) | 0.0400 (14) | 0.0504 (15) | 0.0029 (11) | 0.0117 (11) | 0.0051 (11) |
C28 | 0.0372 (12) | 0.0358 (13) | 0.0440 (14) | 0.0013 (10) | 0.0083 (10) | 0.0058 (11) |
N29 | 0.0357 (10) | 0.0312 (11) | 0.0433 (12) | −0.0009 (8) | 0.0050 (9) | 0.0001 (9) |
N30 | 0.0306 (10) | 0.0312 (11) | 0.0490 (12) | −0.0001 (8) | 0.0084 (9) | 0.0018 (9) |
C31 | 0.0343 (12) | 0.0346 (12) | 0.0388 (12) | 0.0042 (9) | 0.0112 (10) | 0.0098 (10) |
O32 | 0.0352 (9) | 0.0441 (10) | 0.0609 (11) | 0.0022 (8) | 0.0176 (8) | 0.0061 (8) |
C33 | 0.0345 (12) | 0.0323 (13) | 0.0407 (13) | 0.0066 (10) | 0.0083 (10) | 0.0107 (11) |
C34 | 0.0433 (13) | 0.0350 (13) | 0.0466 (14) | 0.0019 (11) | 0.0136 (11) | 0.0090 (11) |
C35 | 0.0497 (15) | 0.0380 (14) | 0.0552 (17) | −0.0019 (12) | 0.0103 (13) | 0.0118 (12) |
N36 | 0.0615 (16) | 0.0351 (12) | 0.0516 (14) | 0.0001 (11) | 0.0039 (12) | 0.0020 (10) |
C37 | 0.0619 (18) | 0.0457 (16) | 0.0435 (15) | 0.0087 (14) | 0.0124 (13) | 0.0007 (12) |
C38 | 0.0450 (14) | 0.0447 (14) | 0.0422 (14) | 0.0050 (11) | 0.0140 (11) | 0.0080 (11) |
Geometric parameters (Å, º) top
I1—C2 | 2.098 (3) | I21—C22 | 2.105 (3) |
C2—C3 | 1.378 (4) | C22—C23 | 1.383 (4) |
C2—C7 | 1.396 (4) | C22—C27 | 1.385 (4) |
C3—C4 | 1.382 (4) | C23—C24 | 1.392 (4) |
C3—H3 | 0.9300 | C23—H23 | 0.9300 |
C4—C5 | 1.398 (4) | C24—C25 | 1.391 (4) |
C4—H4 | 0.9300 | C24—H24 | 0.9300 |
C5—C6 | 1.393 (4) | C25—C26 | 1.390 (4) |
C5—C8 | 1.460 (4) | C25—C28 | 1.461 (4) |
C6—C7 | 1.377 (4) | C26—C27 | 1.381 (4) |
C6—H6 | 0.9300 | C26—H26 | 0.9300 |
C7—H7 | 0.9300 | C27—H27 | 0.9300 |
C8—N9 | 1.276 (4) | C28—N29 | 1.278 (4) |
C8—H8 | 0.9300 | C28—H28 | 0.9300 |
N9—N10 | 1.375 (3) | N29—N30 | 1.382 (3) |
N10—C11 | 1.358 (3) | N30—C31 | 1.348 (3) |
N10—H10 | 0.8600 | N30—H30 | 0.8600 |
C11—O12 | 1.219 (3) | C31—O32 | 1.222 (3) |
C11—C13 | 1.487 (3) | C31—C33 | 1.494 (3) |
C13—C14 | 1.386 (4) | C33—C38 | 1.388 (4) |
C13—C18 | 1.391 (4) | C33—C34 | 1.391 (4) |
C14—C15 | 1.384 (4) | C34—C35 | 1.384 (4) |
C14—H14 | 0.9300 | C34—H34 | 0.9300 |
C15—N16 | 1.333 (4) | C35—N36 | 1.332 (4) |
C15—H15 | 0.9300 | C35—H35 | 0.9300 |
N16—C17 | 1.326 (4) | N36—C37 | 1.330 (4) |
C17—C18 | 1.382 (4) | C37—C38 | 1.385 (4) |
C17—H17 | 0.9300 | C37—H37 | 0.9300 |
C18—H18 | 0.9300 | C38—H38 | 0.9300 |
| | | |
C3—C2—C7 | 120.0 (2) | C23—C22—C27 | 120.6 (2) |
C3—C2—I1 | 119.7 (2) | C23—C22—I21 | 119.4 (2) |
C7—C2—I1 | 120.3 (2) | C27—C22—I21 | 120.0 (2) |
C2—C3—C4 | 120.0 (3) | C22—C23—C24 | 119.4 (3) |
C2—C3—H3 | 120.0 | C22—C23—H23 | 120.3 |
C4—C3—H3 | 120.0 | C24—C23—H23 | 120.3 |
C3—C4—C5 | 120.7 (3) | C25—C24—C23 | 120.7 (3) |
C3—C4—H4 | 119.7 | C25—C24—H24 | 119.7 |
C5—C4—H4 | 119.7 | C23—C24—H24 | 119.7 |
C6—C5—C4 | 118.8 (2) | C26—C25—C24 | 118.8 (2) |
C6—C5—C8 | 122.4 (2) | C26—C25—C28 | 122.0 (2) |
C4—C5—C8 | 118.8 (2) | C24—C25—C28 | 119.2 (2) |
C7—C6—C5 | 120.6 (2) | C27—C26—C25 | 120.9 (3) |
C7—C6—H6 | 119.7 | C27—C26—H26 | 119.5 |
C5—C6—H6 | 119.7 | C25—C26—H26 | 119.5 |
C6—C7—C2 | 120.0 (2) | C26—C27—C22 | 119.6 (3) |
C6—C7—H7 | 120.0 | C26—C27—H27 | 120.2 |
C2—C7—H7 | 120.0 | C22—C27—H27 | 120.2 |
N9—C8—C5 | 122.5 (2) | N29—C28—C25 | 121.6 (2) |
N9—C8—H8 | 118.8 | N29—C28—H28 | 119.2 |
C5—C8—H8 | 118.8 | C25—C28—H28 | 119.2 |
C8—N9—N10 | 114.7 (2) | C28—N29—N30 | 114.4 (2) |
C11—N10—N9 | 120.0 (2) | C31—N30—N29 | 119.7 (2) |
C11—N10—H10 | 120.0 | C31—N30—H30 | 120.2 |
N9—N10—H10 | 120.0 | N29—N30—H30 | 120.2 |
O12—C11—N10 | 123.2 (2) | O32—C31—N30 | 123.8 (2) |
O12—C11—C13 | 121.5 (2) | O32—C31—C33 | 120.8 (2) |
N10—C11—C13 | 115.3 (2) | N30—C31—C33 | 115.4 (2) |
C14—C13—C18 | 117.6 (2) | C38—C33—C34 | 117.3 (2) |
C14—C13—C11 | 124.3 (2) | C38—C33—C31 | 118.7 (2) |
C18—C13—C11 | 118.1 (2) | C34—C33—C31 | 123.9 (2) |
C15—C14—C13 | 119.1 (2) | C35—C34—C33 | 119.0 (3) |
C15—C14—H14 | 120.5 | C35—C34—H34 | 120.5 |
C13—C14—H14 | 120.5 | C33—C34—H34 | 120.5 |
N16—C15—C14 | 123.6 (3) | N36—C35—C34 | 124.0 (3) |
N16—C15—H15 | 118.2 | N36—C35—H35 | 118.0 |
C14—C15—H15 | 118.2 | C34—C35—H35 | 118.0 |
C17—N16—C15 | 116.8 (2) | C37—N36—C35 | 116.6 (3) |
N16—C17—C18 | 124.2 (3) | N36—C37—C38 | 123.9 (3) |
N16—C17—H17 | 117.9 | N36—C37—H37 | 118.1 |
C18—C17—H17 | 117.9 | C38—C37—H37 | 118.1 |
C17—C18—C13 | 118.7 (2) | C37—C38—C33 | 119.2 (3) |
C17—C18—H18 | 120.6 | C37—C38—H38 | 120.4 |
C13—C18—H18 | 120.6 | C33—C38—H38 | 120.4 |
| | | |
C7—C2—C3—C4 | 1.3 (4) | C27—C22—C23—C24 | 1.3 (5) |
I1—C2—C3—C4 | −177.9 (2) | I21—C22—C23—C24 | −179.6 (2) |
C2—C3—C4—C5 | −0.1 (4) | C22—C23—C24—C25 | 0.2 (5) |
C3—C4—C5—C6 | −1.5 (4) | C23—C24—C25—C26 | −1.5 (5) |
C3—C4—C5—C8 | −179.2 (3) | C23—C24—C25—C28 | 178.3 (3) |
C4—C5—C6—C7 | 1.9 (4) | C24—C25—C26—C27 | 1.3 (4) |
C8—C5—C6—C7 | 179.6 (3) | C28—C25—C26—C27 | −178.5 (3) |
C5—C6—C7—C2 | −0.8 (4) | C25—C26—C27—C22 | 0.2 (5) |
C3—C2—C7—C6 | −0.9 (4) | C23—C22—C27—C26 | −1.5 (4) |
I1—C2—C7—C6 | 178.3 (2) | I21—C22—C27—C26 | 179.4 (2) |
C6—C5—C8—N9 | 11.5 (4) | C26—C25—C28—N29 | 10.7 (4) |
C4—C5—C8—N9 | −170.9 (3) | C24—C25—C28—N29 | −169.1 (3) |
C5—C8—N9—N10 | −176.0 (2) | C25—C28—N29—N30 | −178.5 (2) |
C8—N9—N10—C11 | −176.1 (2) | C28—N29—N30—C31 | −168.7 (2) |
N9—N10—C11—O12 | 5.6 (4) | N29—N30—C31—O32 | 1.2 (4) |
N9—N10—C11—C13 | −175.1 (2) | N29—N30—C31—C33 | −179.5 (2) |
O12—C11—C13—C14 | 147.1 (3) | O32—C31—C33—C38 | −28.3 (4) |
N10—C11—C13—C14 | −32.2 (4) | N30—C31—C33—C38 | 152.5 (3) |
O12—C11—C13—C18 | −31.5 (4) | O32—C31—C33—C34 | 147.7 (3) |
N10—C11—C13—C18 | 149.2 (2) | N30—C31—C33—C34 | −31.5 (4) |
C18—C13—C14—C15 | 1.3 (4) | C38—C33—C34—C35 | 1.3 (4) |
C11—C13—C14—C15 | −177.3 (3) | C31—C33—C34—C35 | −174.8 (3) |
C13—C14—C15—N16 | −0.1 (5) | C33—C34—C35—N36 | −0.6 (5) |
C14—C15—N16—C17 | −1.3 (5) | C34—C35—N36—C37 | −0.9 (5) |
C15—N16—C17—C18 | 1.4 (5) | C35—N36—C37—C38 | 1.8 (5) |
N16—C17—C18—C13 | −0.2 (5) | N36—C37—C38—C33 | −1.1 (5) |
C14—C13—C18—C17 | −1.2 (4) | C34—C33—C38—C37 | −0.4 (4) |
C11—C13—C18—C17 | 177.5 (2) | C31—C33—C38—C37 | 175.8 (3) |
Crystal data top
C15H11IN4 | Dx = 1.711 Mg m−3 |
Mr = 374.18 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, I41 | Cell parameters from 6953 reflections |
a = 15.0197 (4) Å | θ = 3.4–25.1° |
c = 12.8791 (6) Å | µ = 2.20 mm−1 |
V = 2905.40 (19) Å3 | T = 297 K |
Z = 8 | Needle, yellow |
F(000) = 1456 | 0.50 × 0.02 × 0.02 mm |
Data collection top
MAR345 image plate diffractometer | 2616 independent reflections |
Radiation source: Rigaku UltraX 18 rotating anode | 2374 reflections with I > 2σ(I) |
Xenocs Fox3D mirror monochromator | Rint = 0.040 |
130 images, ΔΦ 2.0° scans | θmax = 25.3°, θmin = 3.4° |
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | h = −18→17 |
Tmin = 0.905, Tmax = 1.000 | k = −18→18 |
13780 measured reflections | l = −15→15 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.033P)2 + 7.2193P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.083 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 1.17 e Å−3 |
2616 reflections | Δρmin = −0.60 e Å−3 |
181 parameters | Absolute structure: Flack x determined using 1029 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
1 restraint | Absolute structure parameter: 0.050 (12) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 1.19416 (3) | 0.61072 (5) | 0.73045 (5) | 0.0820 (3) | |
C2 | 1.0607 (5) | 0.6259 (5) | 0.6871 (6) | 0.0496 (18) | |
C3 | 1.0001 (5) | 0.6518 (6) | 0.7621 (6) | 0.0565 (19) | |
H3 | 1.0190 | 0.6649 | 0.8292 | 0.068* | |
C4 | 0.9114 (5) | 0.6577 (6) | 0.7359 (8) | 0.0574 (19) | |
H4 | 0.8704 | 0.6742 | 0.7864 | 0.069* | |
C5 | 0.8818 (5) | 0.6397 (5) | 0.6362 (5) | 0.0416 (15) | |
C6 | 0.9454 (5) | 0.6171 (5) | 0.5618 (5) | 0.0472 (16) | |
H6 | 0.9275 | 0.6067 | 0.4937 | 0.057* | |
C7 | 1.0338 (5) | 0.6100 (5) | 0.5875 (6) | 0.0496 (17) | |
H7 | 1.0754 | 0.5943 | 0.5371 | 0.059* | |
C8 | 0.7879 (5) | 0.6436 (5) | 0.6154 (5) | 0.0454 (16) | |
H8 | 0.7499 | 0.6585 | 0.6697 | 0.054* | |
N9 | 0.7538 (4) | 0.6278 (4) | 0.5274 (4) | 0.0450 (13) | |
N10 | 0.6604 (4) | 0.6325 (4) | 0.5279 (4) | 0.0462 (14) | |
C11 | 0.6275 (5) | 0.6246 (5) | 0.4349 (5) | 0.0437 (16) | |
N12 | 0.6754 (4) | 0.6196 (4) | 0.3460 (5) | 0.0507 (15) | |
H12 | 0.7323 | 0.6205 | 0.3529 | 0.061* | |
N13 | 0.6442 (5) | 0.6132 (5) | 0.2473 (5) | 0.0622 (17) | |
C14 | 0.5585 (5) | 0.6135 (6) | 0.2388 (7) | 0.065 (2) | |
H14 | 0.5352 | 0.6098 | 0.1721 | 0.078* | |
C15 | 0.4964 (5) | 0.6188 (5) | 0.3220 (6) | 0.0556 (19) | |
C16 | 0.4052 (6) | 0.6166 (7) | 0.3080 (8) | 0.076 (3) | |
H16 | 0.3818 | 0.6143 | 0.2412 | 0.092* | |
C17 | 0.3499 (7) | 0.6177 (8) | 0.3907 (10) | 0.090 (3) | |
H17 | 0.2886 | 0.6154 | 0.3804 | 0.108* | |
C18 | 0.3838 (7) | 0.6220 (8) | 0.4912 (10) | 0.092 (3) | |
H18 | 0.3453 | 0.6235 | 0.5477 | 0.111* | |
C19 | 0.4744 (5) | 0.6243 (6) | 0.5070 (7) | 0.068 (2) | |
H19 | 0.4975 | 0.6263 | 0.5740 | 0.081* | |
C20 | 0.5304 (5) | 0.6234 (5) | 0.4221 (6) | 0.0482 (16) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.0452 (3) | 0.1142 (5) | 0.0865 (4) | 0.0027 (3) | −0.0038 (3) | 0.0152 (4) |
C2 | 0.044 (4) | 0.047 (4) | 0.058 (4) | −0.002 (3) | 0.000 (3) | 0.008 (3) |
C3 | 0.054 (4) | 0.070 (5) | 0.045 (4) | 0.002 (4) | −0.006 (3) | 0.003 (4) |
C4 | 0.055 (4) | 0.077 (5) | 0.040 (4) | 0.010 (3) | 0.000 (4) | −0.003 (4) |
C5 | 0.048 (4) | 0.044 (4) | 0.033 (3) | 0.004 (3) | 0.002 (3) | 0.001 (3) |
C6 | 0.057 (4) | 0.048 (4) | 0.036 (3) | −0.003 (3) | 0.002 (3) | −0.002 (3) |
C7 | 0.049 (4) | 0.051 (4) | 0.049 (4) | −0.002 (3) | 0.012 (3) | 0.001 (3) |
C8 | 0.049 (4) | 0.054 (4) | 0.033 (3) | 0.004 (3) | 0.007 (3) | 0.003 (3) |
N9 | 0.043 (3) | 0.056 (4) | 0.035 (3) | 0.002 (3) | 0.000 (2) | 0.002 (2) |
N10 | 0.043 (3) | 0.059 (4) | 0.037 (3) | 0.000 (3) | 0.004 (3) | −0.002 (3) |
C11 | 0.050 (4) | 0.046 (4) | 0.035 (4) | −0.002 (3) | 0.004 (3) | −0.007 (3) |
N12 | 0.048 (3) | 0.069 (4) | 0.035 (3) | 0.000 (3) | −0.002 (3) | −0.007 (3) |
N13 | 0.072 (4) | 0.083 (5) | 0.031 (3) | −0.001 (3) | −0.002 (3) | −0.006 (3) |
C14 | 0.068 (5) | 0.086 (6) | 0.040 (4) | 0.002 (4) | −0.010 (5) | −0.008 (4) |
C15 | 0.057 (5) | 0.062 (5) | 0.048 (4) | −0.006 (4) | −0.011 (4) | −0.011 (4) |
C16 | 0.063 (6) | 0.088 (7) | 0.078 (6) | 0.003 (5) | −0.021 (5) | −0.022 (5) |
C17 | 0.051 (5) | 0.117 (9) | 0.102 (9) | −0.005 (5) | −0.010 (6) | −0.030 (7) |
C18 | 0.064 (6) | 0.132 (9) | 0.081 (7) | 0.001 (6) | 0.018 (5) | −0.031 (8) |
C19 | 0.049 (4) | 0.095 (6) | 0.059 (6) | 0.003 (4) | 0.003 (4) | −0.014 (4) |
C20 | 0.049 (4) | 0.050 (4) | 0.046 (4) | 0.001 (3) | −0.001 (3) | −0.009 (3) |
Geometric parameters (Å, º) top
I1—C2 | 2.093 (7) | C11—C20 | 1.469 (10) |
C2—C7 | 1.367 (11) | N12—N13 | 1.359 (9) |
C2—C3 | 1.383 (11) | N12—H12 | 0.8600 |
C3—C4 | 1.377 (11) | N13—C14 | 1.291 (10) |
C3—H3 | 0.9300 | C14—C15 | 1.422 (12) |
C4—C5 | 1.386 (12) | C14—H14 | 0.9300 |
C4—H4 | 0.9300 | C15—C16 | 1.382 (12) |
C5—C6 | 1.394 (10) | C15—C20 | 1.388 (11) |
C5—C8 | 1.438 (10) | C16—C17 | 1.351 (15) |
C6—C7 | 1.374 (10) | C16—H16 | 0.9300 |
C6—H6 | 0.9300 | C17—C18 | 1.393 (17) |
C7—H7 | 0.9300 | C17—H17 | 0.9300 |
C8—N9 | 1.265 (9) | C18—C19 | 1.375 (13) |
C8—H8 | 0.9300 | C18—H18 | 0.9300 |
N9—N10 | 1.405 (9) | C19—C20 | 1.381 (11) |
N10—C11 | 1.300 (9) | C19—H19 | 0.9300 |
C11—N12 | 1.353 (9) | | |
| | | |
C7—C2—C3 | 120.7 (7) | C11—N12—N13 | 127.8 (6) |
C7—C2—I1 | 120.9 (6) | C11—N12—H12 | 116.1 |
C3—C2—I1 | 118.3 (6) | N13—N12—H12 | 116.1 |
C4—C3—C2 | 118.9 (8) | C14—N13—N12 | 115.0 (7) |
C4—C3—H3 | 120.5 | N13—C14—C15 | 126.2 (8) |
C2—C3—H3 | 120.5 | N13—C14—H14 | 116.9 |
C3—C4—C5 | 121.6 (8) | C15—C14—H14 | 116.9 |
C3—C4—H4 | 119.2 | C16—C15—C20 | 119.1 (8) |
C5—C4—H4 | 119.2 | C16—C15—C14 | 123.4 (8) |
C4—C5—C6 | 117.7 (7) | C20—C15—C14 | 117.5 (7) |
C4—C5—C8 | 118.7 (6) | C17—C16—C15 | 120.5 (9) |
C6—C5—C8 | 123.6 (6) | C17—C16—H16 | 119.7 |
C7—C6—C5 | 121.0 (7) | C15—C16—H16 | 119.7 |
C7—C6—H6 | 119.5 | C16—C17—C18 | 120.5 (9) |
C5—C6—H6 | 119.5 | C16—C17—H17 | 119.8 |
C2—C7—C6 | 119.9 (7) | C18—C17—H17 | 119.8 |
C2—C7—H7 | 120.1 | C19—C18—C17 | 120.1 (10) |
C6—C7—H7 | 120.1 | C19—C18—H18 | 120.0 |
N9—C8—C5 | 123.8 (6) | C17—C18—H18 | 120.0 |
N9—C8—H8 | 118.1 | C18—C19—C20 | 119.0 (9) |
C5—C8—H8 | 118.1 | C18—C19—H19 | 120.5 |
C8—N9—N10 | 113.0 (6) | C20—C19—H19 | 120.5 |
C11—N10—N9 | 111.8 (5) | C19—C20—C15 | 120.9 (7) |
N10—C11—N12 | 125.6 (7) | C19—C20—C11 | 121.1 (7) |
N10—C11—C20 | 118.8 (6) | C15—C20—C11 | 118.0 (7) |
N12—C11—C20 | 115.6 (6) | | |
| | | |
C7—C2—C3—C4 | 2.6 (12) | N12—N13—C14—C15 | −0.6 (13) |
I1—C2—C3—C4 | −176.8 (6) | N13—C14—C15—C16 | −178.3 (9) |
C2—C3—C4—C5 | −0.9 (13) | N13—C14—C15—C20 | −0.7 (14) |
C3—C4—C5—C6 | −1.5 (12) | C20—C15—C16—C17 | −0.8 (15) |
C3—C4—C5—C8 | 177.5 (7) | C14—C15—C16—C17 | 176.8 (10) |
C4—C5—C6—C7 | 2.2 (11) | C15—C16—C17—C18 | 0.7 (18) |
C8—C5—C6—C7 | −176.6 (7) | C16—C17—C18—C19 | −0.8 (19) |
C3—C2—C7—C6 | −1.9 (12) | C17—C18—C19—C20 | 0.9 (17) |
I1—C2—C7—C6 | 177.5 (5) | C18—C19—C20—C15 | −1.1 (14) |
C5—C6—C7—C2 | −0.6 (11) | C18—C19—C20—C11 | −179.3 (8) |
C4—C5—C8—N9 | −179.6 (7) | C16—C15—C20—C19 | 1.0 (13) |
C6—C5—C8—N9 | −0.7 (11) | C14—C15—C20—C19 | −176.8 (8) |
C5—C8—N9—N10 | 177.6 (6) | C16—C15—C20—C11 | 179.3 (8) |
C8—N9—N10—C11 | 173.8 (7) | C14—C15—C20—C11 | 1.5 (11) |
N9—N10—C11—N12 | −4.9 (11) | N10—C11—C20—C19 | −4.4 (12) |
N9—N10—C11—C20 | 176.8 (6) | N12—C11—C20—C19 | 177.2 (8) |
N10—C11—N12—N13 | −178.5 (8) | N10—C11—C20—C15 | 177.3 (8) |
C20—C11—N12—N13 | −0.3 (11) | N12—C11—C20—C15 | −1.1 (10) |
C11—N12—N13—C14 | 1.1 (12) | | |
Crystal data top
C15H11BrN4 | F(000) = 656 |
Mr = 327.19 | Dx = 1.626 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.8761 (7) Å | Cell parameters from 6643 reflections |
b = 4.0269 (2) Å | θ = 3.6–26.1° |
c = 23.1830 (12) Å | µ = 3.07 mm−1 |
β = 105.810 (5)° | T = 297 K |
V = 1336.24 (12) Å3 | Rod, yellow |
Z = 4 | 0.50 × 0.12 × 0.07 mm |
Data collection top
MAR345 image plate diffractometer | 2600 independent reflections |
Radiation source: Rigaku UltraX 18 rotating anode | 2284 reflections with I > 2σ(I) |
Xenocs Fox3D mirror monochromator | Rint = 0.049 |
135 images, ΔΦ 2.0° scans | θmax = 26.2°, θmin = 3.5° |
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | h = −18→18 |
Tmin = 0.378, Tmax = 1.000 | k = −4→4 |
12533 measured reflections | l = −28→28 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.111 | w = 1/[σ2(Fo2) + (0.0599P)2 + 0.5605P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
2600 reflections | Δρmax = 0.41 e Å−3 |
181 parameters | Δρmin = −0.49 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br1 | 0.96756 (2) | 0.58076 (10) | 0.82238 (2) | 0.07469 (18) | |
C2 | 0.84000 (18) | 0.5188 (7) | 0.78026 (12) | 0.0501 (6) | |
C3 | 0.78232 (19) | 0.3540 (7) | 0.80791 (11) | 0.0524 (6) | |
H3 | 0.8061 | 0.2669 | 0.8462 | 0.063* | |
C4 | 0.68893 (19) | 0.3190 (7) | 0.77837 (11) | 0.0511 (6) | |
H4 | 0.6497 | 0.2072 | 0.7969 | 0.061* | |
C5 | 0.65269 (18) | 0.4500 (6) | 0.72087 (11) | 0.0445 (5) | |
C6 | 0.71300 (19) | 0.6132 (6) | 0.69396 (11) | 0.0511 (6) | |
H6 | 0.6900 | 0.6986 | 0.6555 | 0.061* | |
C7 | 0.80671 (19) | 0.6507 (7) | 0.72344 (11) | 0.0541 (6) | |
H7 | 0.8465 | 0.7625 | 0.7053 | 0.065* | |
C8 | 0.55325 (19) | 0.4074 (6) | 0.69022 (11) | 0.0482 (6) | |
H8 | 0.5164 | 0.2807 | 0.7084 | 0.058* | |
N9 | 0.51604 (14) | 0.5390 (5) | 0.63948 (9) | 0.0471 (5) | |
N10 | 0.42153 (14) | 0.4587 (5) | 0.61789 (9) | 0.0479 (5) | |
C11 | 0.38520 (16) | 0.5713 (6) | 0.56375 (10) | 0.0416 (5) | |
N12 | 0.43243 (13) | 0.7541 (6) | 0.53221 (9) | 0.0473 (5) | |
H12 | 0.4890 | 0.8072 | 0.5505 | 0.057* | |
N13 | 0.39918 (16) | 0.8617 (6) | 0.47452 (9) | 0.0523 (5) | |
C14 | 0.31429 (18) | 0.7856 (7) | 0.44714 (11) | 0.0512 (6) | |
H14 | 0.2911 | 0.8534 | 0.4075 | 0.061* | |
C15 | 0.25314 (17) | 0.6031 (6) | 0.47371 (11) | 0.0466 (5) | |
C16 | 0.16031 (19) | 0.5311 (7) | 0.44273 (13) | 0.0573 (6) | |
H16 | 0.1371 | 0.5946 | 0.4029 | 0.069* | |
C17 | 0.10373 (19) | 0.3672 (8) | 0.47111 (15) | 0.0645 (7) | |
H17 | 0.0418 | 0.3237 | 0.4507 | 0.077* | |
C18 | 0.13881 (19) | 0.2659 (8) | 0.53040 (14) | 0.0629 (7) | |
H18 | 0.1000 | 0.1547 | 0.5493 | 0.076* | |
C19 | 0.22996 (19) | 0.3279 (7) | 0.56127 (12) | 0.0524 (6) | |
H19 | 0.2529 | 0.2568 | 0.6007 | 0.063* | |
C20 | 0.28799 (16) | 0.4984 (6) | 0.53313 (11) | 0.0426 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0510 (2) | 0.0902 (3) | 0.0719 (2) | −0.00186 (13) | −0.00184 (15) | −0.00538 (16) |
C2 | 0.0473 (13) | 0.0529 (13) | 0.0462 (13) | 0.0038 (10) | 0.0059 (10) | −0.0078 (11) |
C3 | 0.0571 (14) | 0.0575 (14) | 0.0387 (11) | 0.0056 (11) | 0.0066 (10) | 0.0029 (11) |
C4 | 0.0567 (14) | 0.0560 (14) | 0.0420 (12) | 0.0014 (11) | 0.0156 (10) | 0.0053 (11) |
C5 | 0.0474 (13) | 0.0466 (12) | 0.0382 (11) | 0.0028 (10) | 0.0093 (9) | −0.0022 (10) |
C6 | 0.0571 (14) | 0.0561 (14) | 0.0382 (11) | 0.0000 (11) | 0.0101 (10) | 0.0064 (10) |
C7 | 0.0528 (14) | 0.0621 (15) | 0.0468 (13) | −0.0054 (12) | 0.0125 (11) | 0.0026 (12) |
C8 | 0.0506 (13) | 0.0518 (14) | 0.0430 (12) | −0.0001 (10) | 0.0144 (10) | 0.0005 (10) |
N9 | 0.0420 (10) | 0.0555 (11) | 0.0422 (10) | −0.0012 (9) | 0.0084 (8) | −0.0016 (9) |
N10 | 0.0436 (11) | 0.0569 (12) | 0.0428 (10) | −0.0019 (9) | 0.0112 (9) | −0.0012 (9) |
C11 | 0.0412 (11) | 0.0456 (12) | 0.0399 (11) | 0.0018 (9) | 0.0143 (9) | −0.0043 (9) |
N12 | 0.0386 (10) | 0.0598 (12) | 0.0444 (10) | −0.0038 (9) | 0.0128 (8) | 0.0007 (9) |
N13 | 0.0549 (12) | 0.0604 (13) | 0.0439 (10) | −0.0019 (10) | 0.0176 (9) | 0.0025 (10) |
C14 | 0.0521 (14) | 0.0599 (15) | 0.0398 (11) | 0.0039 (12) | 0.0097 (10) | 0.0034 (11) |
C15 | 0.0429 (12) | 0.0480 (13) | 0.0483 (12) | 0.0034 (9) | 0.0113 (10) | −0.0062 (10) |
C16 | 0.0457 (14) | 0.0657 (16) | 0.0526 (14) | 0.0053 (12) | 0.0000 (11) | −0.0050 (13) |
C17 | 0.0383 (13) | 0.0728 (18) | 0.0768 (18) | −0.0053 (12) | 0.0062 (12) | −0.0149 (15) |
C18 | 0.0489 (14) | 0.0689 (18) | 0.0757 (18) | −0.0134 (13) | 0.0249 (13) | −0.0090 (15) |
C19 | 0.0524 (14) | 0.0560 (14) | 0.0520 (13) | −0.0067 (12) | 0.0195 (11) | −0.0051 (12) |
C20 | 0.0401 (11) | 0.0437 (11) | 0.0453 (12) | 0.0009 (9) | 0.0137 (9) | −0.0064 (10) |
Geometric parameters (Å, º) top
Br1—C2 | 1.899 (3) | C11—C20 | 1.457 (3) |
C2—C3 | 1.374 (4) | N12—N13 | 1.364 (3) |
C2—C7 | 1.381 (4) | N12—H12 | 0.8600 |
C3—C4 | 1.379 (4) | N13—C14 | 1.286 (3) |
C3—H3 | 0.9300 | C14—C15 | 1.433 (4) |
C4—C5 | 1.398 (3) | C14—H14 | 0.9300 |
C4—H4 | 0.9300 | C15—C20 | 1.398 (4) |
C5—C6 | 1.390 (4) | C15—C16 | 1.402 (4) |
C5—C8 | 1.466 (4) | C16—C17 | 1.371 (4) |
C6—C7 | 1.383 (4) | C16—H16 | 0.9300 |
C6—H6 | 0.9300 | C17—C18 | 1.392 (5) |
C7—H7 | 0.9300 | C17—H17 | 0.9300 |
C8—N9 | 1.271 (3) | C18—C19 | 1.373 (4) |
C8—H8 | 0.9300 | C18—H18 | 0.9300 |
N9—N10 | 1.396 (3) | C19—C20 | 1.396 (4) |
N10—C11 | 1.305 (3) | C19—H19 | 0.9300 |
C11—N12 | 1.360 (3) | | |
| | | |
C3—C2—C7 | 121.6 (2) | C11—N12—N13 | 126.6 (2) |
C3—C2—Br1 | 119.1 (2) | C11—N12—H12 | 116.7 |
C7—C2—Br1 | 119.2 (2) | N13—N12—H12 | 116.7 |
C2—C3—C4 | 119.4 (2) | C14—N13—N12 | 116.9 (2) |
C2—C3—H3 | 120.3 | N13—C14—C15 | 124.3 (2) |
C4—C3—H3 | 120.3 | N13—C14—H14 | 117.9 |
C3—C4—C5 | 120.7 (2) | C15—C14—H14 | 117.9 |
C3—C4—H4 | 119.7 | C20—C15—C16 | 119.4 (2) |
C5—C4—H4 | 119.7 | C20—C15—C14 | 118.0 (2) |
C6—C5—C4 | 118.6 (2) | C16—C15—C14 | 122.5 (2) |
C6—C5—C8 | 121.8 (2) | C17—C16—C15 | 120.1 (3) |
C4—C5—C8 | 119.6 (2) | C17—C16—H16 | 119.9 |
C7—C6—C5 | 121.1 (2) | C15—C16—H16 | 119.9 |
C7—C6—H6 | 119.4 | C16—C17—C18 | 120.1 (3) |
C5—C6—H6 | 119.4 | C16—C17—H17 | 120.0 |
C2—C7—C6 | 118.7 (2) | C18—C17—H17 | 120.0 |
C2—C7—H7 | 120.6 | C19—C18—C17 | 120.8 (3) |
C6—C7—H7 | 120.6 | C19—C18—H18 | 119.6 |
N9—C8—C5 | 121.8 (2) | C17—C18—H18 | 119.6 |
N9—C8—H8 | 119.1 | C18—C19—C20 | 119.6 (3) |
C5—C8—H8 | 119.1 | C18—C19—H19 | 120.2 |
C8—N9—N10 | 112.2 (2) | C20—C19—H19 | 120.2 |
C11—N10—N9 | 112.15 (19) | C19—C20—C15 | 119.9 (2) |
N10—C11—N12 | 124.5 (2) | C19—C20—C11 | 122.0 (2) |
N10—C11—C20 | 119.6 (2) | C15—C20—C11 | 118.2 (2) |
N12—C11—C20 | 115.9 (2) | | |
| | | |
C7—C2—C3—C4 | 0.0 (4) | N12—N13—C14—C15 | 1.3 (4) |
Br1—C2—C3—C4 | 177.6 (2) | N13—C14—C15—C20 | −0.5 (4) |
C2—C3—C4—C5 | −0.1 (4) | N13—C14—C15—C16 | 178.6 (3) |
C3—C4—C5—C6 | 0.6 (4) | C20—C15—C16—C17 | 1.7 (4) |
C3—C4—C5—C8 | 179.6 (2) | C14—C15—C16—C17 | −177.4 (3) |
C4—C5—C6—C7 | −0.9 (4) | C15—C16—C17—C18 | −1.3 (4) |
C8—C5—C6—C7 | −179.9 (2) | C16—C17—C18—C19 | 0.0 (5) |
C3—C2—C7—C6 | −0.3 (4) | C17—C18—C19—C20 | 0.8 (4) |
Br1—C2—C7—C6 | −177.9 (2) | C18—C19—C20—C15 | −0.3 (4) |
C5—C6—C7—C2 | 0.8 (4) | C18—C19—C20—C11 | 179.9 (2) |
C6—C5—C8—N9 | −5.4 (4) | C16—C15—C20—C19 | −0.9 (4) |
C4—C5—C8—N9 | 175.7 (2) | C14—C15—C20—C19 | 178.2 (2) |
C5—C8—N9—N10 | 178.3 (2) | C16—C15—C20—C11 | 178.8 (2) |
C8—N9—N10—C11 | −174.8 (2) | C14—C15—C20—C11 | −2.0 (3) |
N9—N10—C11—N12 | −1.8 (3) | N10—C11—C20—C19 | 4.1 (4) |
N9—N10—C11—C20 | 177.41 (19) | N12—C11—C20—C19 | −176.7 (2) |
N10—C11—N12—N13 | 176.1 (2) | N10—C11—C20—C15 | −175.6 (2) |
C20—C11—N12—N13 | −3.1 (3) | N12—C11—C20—C15 | 3.6 (3) |
C11—N12—N13—C14 | 0.7 (4) | | |
Crystal data top
C15H12N4O·CH2Cl2 | F(000) = 1440 |
Mr = 349.21 | Dx = 1.445 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.51859 (16) Å | Cell parameters from 11622 reflections |
b = 15.70955 (19) Å | θ = 2.9–26.1° |
c = 21.6869 (3) Å | µ = 0.41 mm−1 |
β = 98.0651 (15)° | T = 297 K |
V = 3210.83 (8) Å3 | Block, yellow |
Z = 8 | 0.5 × 0.5 × 0.32 mm |
Data collection top
MAR345 image plate diffractometer | 6290 independent reflections |
Radiation source: Rigaku UltraX 18 rotating anode | 5748 reflections with I > 2σ(I) |
Xenocs Fox3D mirror monochromator | Rint = 0.020 |
180 images, ΔΦ 1.0° scans | θmax = 26.2°, θmin = 3.1° |
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | h = −11→11 |
Tmin = 0.875, Tmax = 1.000 | k = −18→19 |
22125 measured reflections | l = −26→26 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.136 | w = 1/[σ2(Fo2) + (0.0645P)2 + 4.0926P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
6290 reflections | Δρmax = 1.24 e Å−3 |
417 parameters | Δρmin = −1.13 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.35051 (18) | 0.88621 (10) | 0.74921 (7) | 0.0320 (4) | |
H1 | 0.3749 | 0.8969 | 0.7862 | 0.048* | |
C2 | 0.4026 (2) | 0.80946 (13) | 0.73563 (9) | 0.0234 (4) | |
C3 | 0.4931 (2) | 0.76235 (13) | 0.77871 (9) | 0.0247 (4) | |
H3 | 0.5223 | 0.7842 | 0.8183 | 0.030* | |
C4 | 0.5396 (2) | 0.68304 (13) | 0.76265 (9) | 0.0263 (4) | |
H4 | 0.6008 | 0.6522 | 0.7916 | 0.032* | |
C5 | 0.4965 (2) | 0.64837 (13) | 0.70372 (9) | 0.0231 (4) | |
C6 | 0.4085 (2) | 0.69724 (13) | 0.66047 (9) | 0.0248 (4) | |
H6 | 0.3803 | 0.6758 | 0.6207 | 0.030* | |
C7 | 0.3627 (2) | 0.77691 (14) | 0.67586 (10) | 0.0276 (4) | |
H7 | 0.3052 | 0.8089 | 0.6463 | 0.033* | |
C8 | 0.5489 (2) | 0.56484 (13) | 0.68857 (10) | 0.0264 (4) | |
H8 | 0.6214 | 0.5399 | 0.7158 | 0.032* | |
N9 | 0.49832 (19) | 0.52481 (10) | 0.63907 (8) | 0.0237 (4) | |
N10 | 0.56612 (18) | 0.44685 (10) | 0.63295 (8) | 0.0228 (4) | |
C11 | 0.5176 (2) | 0.40816 (12) | 0.58054 (9) | 0.0203 (4) | |
N12 | 0.40802 (18) | 0.43875 (11) | 0.53938 (8) | 0.0224 (4) | |
H12 | 0.3727 | 0.4868 | 0.5484 | 0.027* | |
N13 | 0.34844 (19) | 0.40097 (11) | 0.48524 (8) | 0.0254 (4) | |
C14 | 0.4020 (2) | 0.32918 (14) | 0.47156 (9) | 0.0272 (4) | |
H14 | 0.3616 | 0.3021 | 0.4352 | 0.033* | |
C15 | 0.5203 (2) | 0.28791 (13) | 0.50863 (9) | 0.0237 (4) | |
C16 | 0.5757 (3) | 0.21036 (14) | 0.49132 (10) | 0.0303 (5) | |
H16 | 0.5342 | 0.1827 | 0.4554 | 0.036* | |
C17 | 0.6916 (3) | 0.17497 (14) | 0.52730 (11) | 0.0328 (5) | |
H17 | 0.7286 | 0.1236 | 0.5156 | 0.039* | |
C18 | 0.7537 (2) | 0.21613 (14) | 0.58152 (10) | 0.0306 (5) | |
H18 | 0.8325 | 0.1922 | 0.6055 | 0.037* | |
C19 | 0.6992 (2) | 0.29181 (13) | 0.59974 (9) | 0.0252 (4) | |
H19 | 0.7409 | 0.3187 | 0.6359 | 0.030* | |
C20 | 0.5807 (2) | 0.32819 (12) | 0.56363 (9) | 0.0206 (4) | |
O21 | 0.19608 (16) | 0.09394 (9) | 0.24541 (7) | 0.0283 (3) | |
H21 | 0.1518 | 0.0748 | 0.2132 | 0.042* | |
C22 | 0.1322 (2) | 0.16628 (12) | 0.26169 (9) | 0.0222 (4) | |
C23 | −0.0055 (2) | 0.18861 (13) | 0.23644 (9) | 0.0260 (4) | |
H23 | −0.0581 | 0.1530 | 0.2077 | 0.031* | |
C24 | −0.0642 (2) | 0.26395 (13) | 0.25427 (9) | 0.0253 (4) | |
H24 | −0.1560 | 0.2785 | 0.2370 | 0.030* | |
C25 | 0.0117 (2) | 0.31825 (13) | 0.29754 (9) | 0.0222 (4) | |
C26 | 0.1491 (2) | 0.29437 (13) | 0.32291 (9) | 0.0260 (4) | |
H26 | 0.2015 | 0.3296 | 0.3521 | 0.031* | |
C27 | 0.2087 (2) | 0.21954 (13) | 0.30554 (9) | 0.0259 (4) | |
H27 | 0.3002 | 0.2046 | 0.3232 | 0.031* | |
C28 | −0.0492 (2) | 0.39912 (13) | 0.31370 (9) | 0.0235 (4) | |
H28 | −0.1386 | 0.4148 | 0.2940 | 0.028* | |
N29 | 0.01772 (19) | 0.44894 (11) | 0.35429 (8) | 0.0237 (4) | |
N30 | −0.05494 (18) | 0.52465 (10) | 0.36330 (8) | 0.0222 (4) | |
C31 | 0.0001 (2) | 0.56323 (12) | 0.41469 (9) | 0.0207 (4) | |
N32 | 0.11503 (18) | 0.53201 (11) | 0.45289 (8) | 0.0225 (4) | |
H32 | 0.1523 | 0.4861 | 0.4409 | 0.027* | |
N33 | 0.17699 (18) | 0.56593 (11) | 0.50801 (8) | 0.0240 (4) | |
C34 | 0.1210 (2) | 0.63445 (13) | 0.52629 (9) | 0.0244 (4) | |
H34 | 0.1602 | 0.6576 | 0.5643 | 0.029* | |
C35 | 0.0014 (2) | 0.67761 (13) | 0.49171 (9) | 0.0227 (4) | |
C36 | −0.0508 (2) | 0.75374 (14) | 0.51304 (10) | 0.0283 (4) | |
H36 | −0.0112 | 0.7762 | 0.5512 | 0.034* | |
C37 | −0.1611 (2) | 0.79547 (14) | 0.47735 (11) | 0.0311 (5) | |
H37 | −0.1943 | 0.8469 | 0.4909 | 0.037* | |
C38 | −0.2226 (2) | 0.76034 (14) | 0.42077 (10) | 0.0297 (5) | |
H38 | −0.2972 | 0.7886 | 0.3969 | 0.036* | |
C39 | −0.1746 (2) | 0.68448 (13) | 0.39975 (9) | 0.0250 (4) | |
H39 | −0.2181 | 0.6610 | 0.3625 | 0.030* | |
C40 | −0.0595 (2) | 0.64259 (12) | 0.43470 (9) | 0.0210 (4) | |
C41 | 0.0803 (3) | 0.96999 (17) | 0.65255 (14) | 0.0452 (6) | |
H41A | −0.0011 | 0.9421 | 0.6660 | 0.054* | |
H41B | 0.1655 | 0.9427 | 0.6733 | 0.054* | |
Cl42 | 0.08127 (9) | 1.07697 (6) | 0.67309 (4) | 0.0650 (3) | |
Cl43 | 0.07280 (8) | 0.95924 (7) | 0.57106 (4) | 0.0715 (3) | |
C44 | 0.4013 (3) | −0.0070 (2) | 0.35576 (14) | 0.0489 (7) | |
H44A | 0.3983 | 0.0277 | 0.3186 | 0.059* | |
H44B | 0.3678 | −0.0636 | 0.3431 | 0.059* | |
Cl45 | 0.57710 (7) | −0.01353 (5) | 0.39314 (4) | 0.0554 (2) | |
Cl46 | 0.28942 (8) | 0.03725 (5) | 0.40485 (4) | 0.0527 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0422 (9) | 0.0242 (8) | 0.0260 (7) | 0.0104 (7) | −0.0079 (7) | −0.0064 (6) |
C2 | 0.0260 (10) | 0.0189 (9) | 0.0244 (10) | 0.0007 (8) | 0.0004 (8) | −0.0015 (8) |
C3 | 0.0306 (11) | 0.0230 (10) | 0.0186 (9) | 0.0006 (8) | −0.0034 (8) | −0.0030 (8) |
C4 | 0.0331 (11) | 0.0228 (10) | 0.0209 (9) | 0.0025 (8) | −0.0042 (8) | 0.0008 (8) |
C5 | 0.0273 (10) | 0.0192 (9) | 0.0222 (9) | −0.0018 (8) | 0.0009 (8) | −0.0014 (7) |
C6 | 0.0281 (10) | 0.0238 (10) | 0.0206 (9) | −0.0016 (8) | −0.0032 (8) | −0.0038 (8) |
C7 | 0.0305 (11) | 0.0259 (10) | 0.0233 (10) | 0.0051 (8) | −0.0066 (8) | −0.0002 (8) |
C8 | 0.0327 (11) | 0.0210 (10) | 0.0233 (10) | 0.0011 (8) | −0.0037 (8) | 0.0006 (8) |
N9 | 0.0294 (9) | 0.0169 (8) | 0.0241 (8) | 0.0009 (7) | 0.0013 (7) | −0.0004 (6) |
N10 | 0.0284 (9) | 0.0173 (8) | 0.0214 (8) | 0.0009 (7) | −0.0014 (7) | −0.0003 (6) |
C11 | 0.0236 (9) | 0.0181 (9) | 0.0192 (9) | −0.0019 (7) | 0.0024 (7) | 0.0033 (7) |
N12 | 0.0271 (9) | 0.0180 (8) | 0.0207 (8) | 0.0014 (7) | −0.0017 (7) | −0.0006 (6) |
N13 | 0.0286 (9) | 0.0270 (9) | 0.0187 (8) | −0.0004 (7) | −0.0030 (7) | 0.0015 (7) |
C14 | 0.0330 (11) | 0.0283 (11) | 0.0186 (9) | −0.0011 (9) | −0.0025 (8) | −0.0028 (8) |
C15 | 0.0293 (10) | 0.0227 (10) | 0.0192 (9) | −0.0014 (8) | 0.0033 (8) | 0.0012 (8) |
C16 | 0.0417 (13) | 0.0247 (10) | 0.0246 (10) | −0.0009 (9) | 0.0049 (9) | −0.0043 (8) |
C17 | 0.0444 (13) | 0.0209 (10) | 0.0345 (12) | 0.0084 (9) | 0.0109 (10) | 0.0006 (9) |
C18 | 0.0313 (11) | 0.0285 (11) | 0.0318 (11) | 0.0083 (9) | 0.0042 (9) | 0.0054 (9) |
C19 | 0.0269 (10) | 0.0248 (10) | 0.0230 (10) | 0.0004 (8) | 0.0002 (8) | 0.0012 (8) |
C20 | 0.0243 (10) | 0.0182 (9) | 0.0193 (9) | −0.0016 (7) | 0.0029 (7) | 0.0015 (7) |
O21 | 0.0345 (8) | 0.0226 (7) | 0.0248 (7) | 0.0038 (6) | −0.0060 (6) | −0.0051 (6) |
C22 | 0.0287 (10) | 0.0201 (9) | 0.0173 (9) | −0.0011 (8) | 0.0017 (7) | 0.0013 (7) |
C23 | 0.0275 (10) | 0.0254 (10) | 0.0230 (10) | −0.0047 (8) | −0.0038 (8) | −0.0049 (8) |
C24 | 0.0242 (10) | 0.0259 (10) | 0.0239 (10) | −0.0009 (8) | −0.0032 (8) | −0.0012 (8) |
C25 | 0.0267 (10) | 0.0211 (9) | 0.0184 (9) | −0.0024 (8) | 0.0011 (7) | 0.0013 (7) |
C26 | 0.0298 (11) | 0.0239 (10) | 0.0219 (9) | −0.0027 (8) | −0.0055 (8) | −0.0036 (8) |
C27 | 0.0253 (10) | 0.0261 (10) | 0.0236 (10) | 0.0015 (8) | −0.0058 (8) | −0.0005 (8) |
C28 | 0.0258 (10) | 0.0235 (10) | 0.0198 (9) | 0.0003 (8) | −0.0014 (7) | 0.0016 (8) |
N29 | 0.0298 (9) | 0.0190 (8) | 0.0211 (8) | 0.0026 (7) | −0.0008 (7) | 0.0002 (6) |
N30 | 0.0283 (9) | 0.0172 (8) | 0.0201 (8) | 0.0019 (6) | −0.0001 (7) | 0.0008 (6) |
C31 | 0.0228 (9) | 0.0194 (9) | 0.0194 (9) | −0.0017 (7) | 0.0013 (7) | 0.0038 (7) |
N32 | 0.0264 (9) | 0.0197 (8) | 0.0200 (8) | 0.0022 (7) | −0.0016 (7) | −0.0009 (6) |
N33 | 0.0251 (9) | 0.0256 (9) | 0.0198 (8) | −0.0010 (7) | −0.0024 (7) | 0.0011 (7) |
C34 | 0.0267 (10) | 0.0268 (10) | 0.0185 (9) | −0.0036 (8) | −0.0009 (8) | −0.0015 (8) |
C35 | 0.0246 (10) | 0.0222 (10) | 0.0209 (9) | −0.0034 (8) | 0.0020 (8) | 0.0004 (8) |
C36 | 0.0318 (11) | 0.0254 (10) | 0.0272 (10) | −0.0024 (8) | 0.0030 (8) | −0.0056 (8) |
C37 | 0.0371 (12) | 0.0217 (10) | 0.0349 (12) | 0.0040 (9) | 0.0065 (9) | −0.0035 (9) |
C38 | 0.0319 (11) | 0.0263 (11) | 0.0300 (11) | 0.0059 (9) | 0.0017 (9) | 0.0045 (9) |
C39 | 0.0297 (11) | 0.0241 (10) | 0.0204 (9) | 0.0007 (8) | 0.0003 (8) | 0.0014 (8) |
C40 | 0.0251 (10) | 0.0185 (9) | 0.0197 (9) | −0.0020 (7) | 0.0037 (7) | 0.0025 (7) |
C41 | 0.0405 (14) | 0.0379 (14) | 0.0551 (16) | 0.0013 (11) | −0.0010 (12) | 0.0142 (12) |
Cl42 | 0.0683 (5) | 0.0620 (5) | 0.0621 (5) | 0.0183 (4) | −0.0004 (4) | −0.0331 (4) |
Cl43 | 0.0477 (4) | 0.0930 (7) | 0.0743 (5) | −0.0117 (4) | 0.0106 (4) | −0.0558 (5) |
C44 | 0.0432 (15) | 0.0532 (17) | 0.0474 (15) | 0.0103 (12) | −0.0037 (12) | −0.0068 (13) |
Cl45 | 0.0365 (4) | 0.0652 (5) | 0.0628 (5) | 0.0060 (3) | 0.0006 (3) | −0.0071 (4) |
Cl46 | 0.0462 (4) | 0.0531 (4) | 0.0604 (4) | 0.0153 (3) | 0.0128 (3) | 0.0121 (3) |
Geometric parameters (Å, º) top
O1—C2 | 1.352 (2) | C23—C24 | 1.387 (3) |
O1—H1 | 0.8200 | C23—H23 | 0.9300 |
C2—C3 | 1.392 (3) | C24—C25 | 1.393 (3) |
C2—C7 | 1.396 (3) | C24—H24 | 0.9300 |
C3—C4 | 1.383 (3) | C25—C26 | 1.398 (3) |
C3—H3 | 0.9300 | C25—C28 | 1.459 (3) |
C4—C5 | 1.397 (3) | C26—C27 | 1.380 (3) |
C4—H4 | 0.9300 | C26—H26 | 0.9300 |
C5—C6 | 1.396 (3) | C27—H27 | 0.9300 |
C5—C8 | 1.457 (3) | C28—N29 | 1.279 (3) |
C6—C7 | 1.381 (3) | C28—H28 | 0.9300 |
C6—H6 | 0.9300 | N29—N30 | 1.403 (2) |
C7—H7 | 0.9300 | N30—C31 | 1.311 (3) |
C8—N9 | 1.278 (3) | C31—N32 | 1.367 (3) |
C8—H8 | 0.9300 | C31—C40 | 1.461 (3) |
N9—N10 | 1.399 (2) | N32—N33 | 1.365 (2) |
N10—C11 | 1.314 (3) | N32—H32 | 0.8600 |
C11—N12 | 1.362 (3) | N33—C34 | 1.288 (3) |
C11—C20 | 1.461 (3) | C34—C35 | 1.441 (3) |
N12—N13 | 1.366 (2) | C34—H34 | 0.9300 |
N12—H12 | 0.8600 | C35—C36 | 1.398 (3) |
N13—C14 | 1.289 (3) | C35—C40 | 1.402 (3) |
C14—C15 | 1.442 (3) | C36—C37 | 1.379 (3) |
C14—H14 | 0.9300 | C36—H36 | 0.9300 |
C15—C16 | 1.400 (3) | C37—C38 | 1.397 (3) |
C15—C20 | 1.401 (3) | C37—H37 | 0.9300 |
C16—C17 | 1.376 (3) | C38—C39 | 1.377 (3) |
C16—H16 | 0.9300 | C38—H38 | 0.9300 |
C17—C18 | 1.398 (3) | C39—C40 | 1.405 (3) |
C17—H17 | 0.9300 | C39—H39 | 0.9300 |
C18—C19 | 1.377 (3) | C41—Cl42 | 1.738 (3) |
C18—H18 | 0.9300 | C41—Cl43 | 1.767 (3) |
C19—C20 | 1.401 (3) | C41—H41A | 0.9700 |
C19—H19 | 0.9300 | C41—H41B | 0.9700 |
O21—C22 | 1.358 (2) | C44—Cl46 | 1.752 (3) |
O21—H21 | 0.8200 | C44—Cl45 | 1.757 (3) |
C22—C27 | 1.393 (3) | C44—H44A | 0.9700 |
C22—C23 | 1.393 (3) | C44—H44B | 0.9700 |
| | | |
C2—O1—H1 | 109.5 | C22—C23—H23 | 120.0 |
O1—C2—C3 | 122.65 (18) | C23—C24—C25 | 121.30 (19) |
O1—C2—C7 | 117.96 (18) | C23—C24—H24 | 119.4 |
C3—C2—C7 | 119.38 (18) | C25—C24—H24 | 119.4 |
C4—C3—C2 | 119.99 (18) | C24—C25—C26 | 117.98 (19) |
C4—C3—H3 | 120.0 | C24—C25—C28 | 120.61 (18) |
C2—C3—H3 | 120.0 | C26—C25—C28 | 121.37 (18) |
C3—C4—C5 | 121.21 (19) | C27—C26—C25 | 121.26 (18) |
C3—C4—H4 | 119.4 | C27—C26—H26 | 119.4 |
C5—C4—H4 | 119.4 | C25—C26—H26 | 119.4 |
C6—C5—C4 | 118.15 (18) | C26—C27—C22 | 120.16 (19) |
C6—C5—C8 | 122.38 (18) | C26—C27—H27 | 119.9 |
C4—C5—C8 | 119.42 (18) | C22—C27—H27 | 119.9 |
C7—C6—C5 | 121.04 (18) | N29—C28—C25 | 121.46 (18) |
C7—C6—H6 | 119.5 | N29—C28—H28 | 119.3 |
C5—C6—H6 | 119.5 | C25—C28—H28 | 119.3 |
C6—C7—C2 | 120.17 (19) | C28—N29—N30 | 114.02 (17) |
C6—C7—H7 | 119.9 | C31—N30—N29 | 111.35 (16) |
C2—C7—H7 | 119.9 | N30—C31—N32 | 122.65 (18) |
N9—C8—C5 | 122.13 (19) | N30—C31—C40 | 121.41 (17) |
N9—C8—H8 | 118.9 | N32—C31—C40 | 115.94 (17) |
C5—C8—H8 | 118.9 | N33—N32—C31 | 126.97 (17) |
C8—N9—N10 | 112.70 (17) | N33—N32—H32 | 116.5 |
C11—N10—N9 | 112.09 (16) | C31—N32—H32 | 116.5 |
N10—C11—N12 | 123.19 (18) | C34—N33—N32 | 116.68 (17) |
N10—C11—C20 | 120.52 (17) | N33—C34—C35 | 124.31 (18) |
N12—C11—C20 | 116.29 (17) | N33—C34—H34 | 117.8 |
C11—N12—N13 | 126.69 (17) | C35—C34—H34 | 117.8 |
C11—N12—H12 | 116.7 | C36—C35—C40 | 120.33 (19) |
N13—N12—H12 | 116.7 | C36—C35—C34 | 121.43 (18) |
C14—N13—N12 | 116.60 (17) | C40—C35—C34 | 118.22 (18) |
N13—C14—C15 | 124.62 (19) | C37—C36—C35 | 119.91 (19) |
N13—C14—H14 | 117.7 | C37—C36—H36 | 120.0 |
C15—C14—H14 | 117.7 | C35—C36—H36 | 120.0 |
C16—C15—C20 | 119.74 (19) | C36—C37—C38 | 119.8 (2) |
C16—C15—C14 | 122.42 (19) | C36—C37—H37 | 120.1 |
C20—C15—C14 | 117.84 (18) | C38—C37—H37 | 120.1 |
C17—C16—C15 | 120.1 (2) | C39—C38—C37 | 121.0 (2) |
C17—C16—H16 | 119.9 | C39—C38—H38 | 119.5 |
C15—C16—H16 | 119.9 | C37—C38—H38 | 119.5 |
C16—C17—C18 | 120.1 (2) | C38—C39—C40 | 119.80 (19) |
C16—C17—H17 | 120.0 | C38—C39—H39 | 120.1 |
C18—C17—H17 | 120.0 | C40—C39—H39 | 120.1 |
C19—C18—C17 | 120.6 (2) | C35—C40—C39 | 119.11 (18) |
C19—C18—H18 | 119.7 | C35—C40—C31 | 117.83 (17) |
C17—C18—H18 | 119.7 | C39—C40—C31 | 123.06 (18) |
C18—C19—C20 | 119.86 (19) | Cl42—C41—Cl43 | 110.30 (15) |
C18—C19—H19 | 120.1 | Cl42—C41—H41A | 109.6 |
C20—C19—H19 | 120.1 | Cl43—C41—H41A | 109.6 |
C15—C20—C19 | 119.60 (18) | Cl42—C41—H41B | 109.6 |
C15—C20—C11 | 117.90 (17) | Cl43—C41—H41B | 109.6 |
C19—C20—C11 | 122.50 (18) | H41A—C41—H41B | 108.1 |
C22—O21—H21 | 109.5 | Cl46—C44—Cl45 | 111.33 (16) |
O21—C22—C27 | 118.02 (18) | Cl46—C44—H44A | 109.4 |
O21—C22—C23 | 122.63 (18) | Cl45—C44—H44A | 109.4 |
C27—C22—C23 | 119.34 (19) | Cl46—C44—H44B | 109.4 |
C24—C23—C22 | 119.94 (18) | Cl45—C44—H44B | 109.4 |
C24—C23—H23 | 120.0 | H44A—C44—H44B | 108.0 |
| | | |
O1—C2—C3—C4 | 178.1 (2) | O21—C22—C23—C24 | −179.07 (19) |
C7—C2—C3—C4 | −1.7 (3) | C27—C22—C23—C24 | 1.1 (3) |
C2—C3—C4—C5 | −0.6 (3) | C22—C23—C24—C25 | −0.4 (3) |
C3—C4—C5—C6 | 2.1 (3) | C23—C24—C25—C26 | −0.3 (3) |
C3—C4—C5—C8 | 179.6 (2) | C23—C24—C25—C28 | 177.22 (19) |
C4—C5—C6—C7 | −1.4 (3) | C24—C25—C26—C27 | 0.3 (3) |
C8—C5—C6—C7 | −178.8 (2) | C28—C25—C26—C27 | −177.20 (19) |
C5—C6—C7—C2 | −0.9 (3) | C25—C26—C27—C22 | 0.4 (3) |
O1—C2—C7—C6 | −177.4 (2) | O21—C22—C27—C26 | 179.07 (18) |
C3—C2—C7—C6 | 2.4 (3) | C23—C22—C27—C26 | −1.1 (3) |
C6—C5—C8—N9 | −12.7 (3) | C24—C25—C28—N29 | 178.5 (2) |
C4—C5—C8—N9 | 170.0 (2) | C26—C25—C28—N29 | −4.0 (3) |
C5—C8—N9—N10 | 178.55 (18) | C25—C28—N29—N30 | 178.85 (17) |
C8—N9—N10—C11 | −177.10 (18) | C28—N29—N30—C31 | 164.67 (18) |
N9—N10—C11—N12 | −3.8 (3) | N29—N30—C31—N32 | 0.8 (3) |
N9—N10—C11—C20 | 176.29 (16) | N29—N30—C31—C40 | −178.71 (16) |
N10—C11—N12—N13 | −177.53 (19) | N30—C31—N32—N33 | −177.83 (18) |
C20—C11—N12—N13 | 2.4 (3) | C40—C31—N32—N33 | 1.7 (3) |
C11—N12—N13—C14 | −0.4 (3) | C31—N32—N33—C34 | 0.4 (3) |
N12—N13—C14—C15 | −1.1 (3) | N32—N33—C34—C35 | −1.7 (3) |
N13—C14—C15—C16 | −179.2 (2) | N33—C34—C35—C36 | −177.4 (2) |
N13—C14—C15—C20 | 0.5 (3) | N33—C34—C35—C40 | 0.7 (3) |
C20—C15—C16—C17 | −1.7 (3) | C40—C35—C36—C37 | −1.2 (3) |
C14—C15—C16—C17 | 177.9 (2) | C34—C35—C36—C37 | 176.9 (2) |
C15—C16—C17—C18 | 0.4 (3) | C35—C36—C37—C38 | 1.7 (3) |
C16—C17—C18—C19 | 0.6 (3) | C36—C37—C38—C39 | −0.2 (3) |
C17—C18—C19—C20 | −0.2 (3) | C37—C38—C39—C40 | −1.7 (3) |
C16—C15—C20—C19 | 2.1 (3) | C36—C35—C40—C39 | −0.7 (3) |
C14—C15—C20—C19 | −177.58 (19) | C34—C35—C40—C39 | −178.90 (18) |
C16—C15—C20—C11 | −178.78 (18) | C36—C35—C40—C31 | 179.64 (18) |
C14—C15—C20—C11 | 1.6 (3) | C34—C35—C40—C31 | 1.5 (3) |
C18—C19—C20—C15 | −1.1 (3) | C38—C39—C40—C35 | 2.2 (3) |
C18—C19—C20—C11 | 179.80 (19) | C38—C39—C40—C31 | −178.23 (19) |
N10—C11—C20—C15 | 177.07 (18) | N30—C31—C40—C35 | 177.02 (18) |
N12—C11—C20—C15 | −2.8 (3) | N32—C31—C40—C35 | −2.5 (3) |
N10—C11—C20—C19 | −3.8 (3) | N30—C31—C40—C39 | −2.6 (3) |
N12—C11—C20—C19 | 176.30 (18) | N32—C31—C40—C39 | 177.84 (18) |
Crystal data top
C13H10BrN3O | F(000) = 608 |
Mr = 304.15 | Dx = 1.640 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 18.763 (3) Å | Cell parameters from 2623 reflections |
b = 6.5126 (7) Å | θ = 3.3–25.3° |
c = 10.1237 (15) Å | µ = 3.33 mm−1 |
β = 95.458 (15)° | T = 297 K |
V = 1231.5 (3) Å3 | Hexagonal plate, colourless |
Z = 4 | 0.18 × 0.18 × 0.03 mm |
Data collection top
MAR345 image plate diffractometer | 2245 independent reflections |
Radiation source: Rigaku UltraX 18 rotating anode | 1785 reflections with I > 2σ(I) |
Xenocs Fox3D mirror monochromator | Rint = 0.059 |
80 images, ΔΦ 2.5° scans | θmax = 25.4°, θmin = 3.3° |
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | h = −22→22 |
Tmin = 0.533, Tmax = 1.000 | k = −7→7 |
8113 measured reflections | l = −11→12 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.0587P)2 + 0.7961P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2245 reflections | Δρmax = 0.43 e Å−3 |
163 parameters | Δρmin = −0.57 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br1 | 0.96154 (3) | 1.35783 (6) | 0.64628 (6) | 0.0835 (3) | |
C2 | 0.8979 (2) | 1.1317 (5) | 0.6458 (4) | 0.0499 (9) | |
C3 | 0.8525 (2) | 1.1150 (5) | 0.7442 (4) | 0.0524 (9) | |
H3 | 0.8518 | 1.2160 | 0.8090 | 0.063* | |
C4 | 0.8083 (2) | 0.9469 (5) | 0.7452 (3) | 0.0471 (8) | |
H4 | 0.7769 | 0.9358 | 0.8107 | 0.057* | |
C5 | 0.80968 (18) | 0.7925 (5) | 0.6498 (3) | 0.0416 (7) | |
C6 | 0.85567 (19) | 0.8164 (5) | 0.5503 (3) | 0.0458 (8) | |
H6 | 0.8567 | 0.7164 | 0.4849 | 0.055* | |
C7 | 0.89904 (19) | 0.9840 (6) | 0.5473 (3) | 0.0516 (8) | |
H7 | 0.9291 | 0.9991 | 0.4800 | 0.062* | |
C8 | 0.76359 (19) | 0.6140 (5) | 0.6590 (3) | 0.0436 (8) | |
H8 | 0.7433 | 0.5908 | 0.7380 | 0.052* | |
N9 | 0.74983 (15) | 0.4875 (4) | 0.5631 (2) | 0.0402 (6) | |
N10 | 0.70509 (16) | 0.3288 (4) | 0.5908 (2) | 0.0418 (6) | |
H10 | 0.6924 | 0.3153 | 0.6698 | 0.050* | |
C11 | 0.68097 (18) | 0.1944 (5) | 0.4955 (3) | 0.0393 (7) | |
O12 | 0.69702 (15) | 0.2019 (4) | 0.3812 (2) | 0.0560 (7) | |
C13 | 0.63082 (16) | 0.0330 (5) | 0.5387 (3) | 0.0361 (7) | |
C14 | 0.58709 (19) | 0.0629 (6) | 0.6394 (3) | 0.0477 (8) | |
H14 | 0.5890 | 0.1853 | 0.6868 | 0.057* | |
C15 | 0.5405 (2) | −0.0915 (6) | 0.6688 (4) | 0.0573 (10) | |
H15 | 0.5104 | −0.0673 | 0.7351 | 0.069* | |
N16 | 0.53605 (18) | −0.2731 (5) | 0.6075 (3) | 0.0567 (8) | |
C17 | 0.5786 (2) | −0.3005 (6) | 0.5116 (4) | 0.0553 (9) | |
H17 | 0.5767 | −0.4261 | 0.4677 | 0.066* | |
C18 | 0.6255 (2) | −0.1536 (5) | 0.4730 (3) | 0.0472 (8) | |
H18 | 0.6532 | −0.1799 | 0.4035 | 0.057* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0776 (4) | 0.0490 (3) | 0.1235 (5) | −0.0193 (2) | 0.0078 (3) | −0.0001 (2) |
C2 | 0.049 (2) | 0.0384 (18) | 0.061 (2) | −0.0016 (15) | −0.0038 (17) | 0.0053 (15) |
C3 | 0.065 (3) | 0.0421 (19) | 0.050 (2) | 0.0059 (17) | 0.0011 (17) | −0.0072 (15) |
C4 | 0.054 (2) | 0.0489 (19) | 0.0391 (17) | 0.0042 (16) | 0.0100 (14) | −0.0018 (15) |
C5 | 0.047 (2) | 0.0429 (17) | 0.0347 (16) | 0.0022 (14) | 0.0023 (13) | 0.0030 (13) |
C6 | 0.050 (2) | 0.0478 (18) | 0.0403 (17) | 0.0003 (15) | 0.0084 (15) | −0.0053 (14) |
C7 | 0.047 (2) | 0.056 (2) | 0.0534 (19) | −0.0061 (17) | 0.0125 (16) | 0.0038 (17) |
C8 | 0.050 (2) | 0.0449 (18) | 0.0370 (17) | −0.0014 (15) | 0.0113 (14) | 0.0023 (14) |
N9 | 0.0448 (16) | 0.0395 (14) | 0.0369 (13) | −0.0019 (12) | 0.0070 (11) | 0.0045 (12) |
N10 | 0.0531 (18) | 0.0448 (15) | 0.0289 (13) | −0.0056 (13) | 0.0103 (11) | 0.0032 (11) |
C11 | 0.0448 (19) | 0.0411 (16) | 0.0324 (16) | 0.0067 (14) | 0.0065 (13) | 0.0027 (13) |
O12 | 0.0762 (19) | 0.0633 (15) | 0.0307 (12) | −0.0109 (14) | 0.0173 (11) | −0.0034 (11) |
C13 | 0.0374 (17) | 0.0395 (16) | 0.0310 (14) | 0.0026 (13) | 0.0015 (12) | 0.0025 (12) |
C14 | 0.052 (2) | 0.0504 (19) | 0.0416 (17) | −0.0064 (16) | 0.0097 (15) | −0.0069 (15) |
C15 | 0.057 (2) | 0.072 (2) | 0.0449 (19) | −0.013 (2) | 0.0171 (17) | −0.0015 (18) |
N16 | 0.061 (2) | 0.0584 (19) | 0.0513 (17) | −0.0138 (17) | 0.0055 (15) | 0.0065 (15) |
C17 | 0.062 (3) | 0.0433 (18) | 0.059 (2) | −0.0016 (17) | −0.0033 (18) | −0.0007 (17) |
C18 | 0.051 (2) | 0.0463 (19) | 0.0450 (18) | 0.0027 (15) | 0.0081 (15) | −0.0047 (14) |
Geometric parameters (Å, º) top
Br1—C2 | 1.895 (3) | N10—C11 | 1.349 (4) |
C2—C3 | 1.375 (6) | N10—H10 | 0.8600 |
C2—C7 | 1.387 (5) | C11—O12 | 1.224 (4) |
C3—C4 | 1.375 (5) | C11—C13 | 1.503 (4) |
C3—H3 | 0.9300 | C13—C14 | 1.381 (4) |
C4—C5 | 1.396 (5) | C13—C18 | 1.385 (4) |
C4—H4 | 0.9300 | C14—C15 | 1.384 (5) |
C5—C6 | 1.397 (5) | C14—H14 | 0.9300 |
C5—C8 | 1.457 (5) | C15—N16 | 1.334 (5) |
C6—C7 | 1.363 (5) | C15—H15 | 0.9300 |
C6—H6 | 0.9300 | N16—C17 | 1.326 (5) |
C7—H7 | 0.9300 | C17—C18 | 1.382 (5) |
C8—N9 | 1.280 (4) | C17—H17 | 0.9300 |
C8—H8 | 0.9300 | C18—H18 | 0.9300 |
N9—N10 | 1.377 (4) | | |
| | | |
C3—C2—C7 | 121.2 (3) | C11—N10—N9 | 120.7 (2) |
C3—C2—Br1 | 119.6 (3) | C11—N10—H10 | 119.6 |
C7—C2—Br1 | 119.2 (3) | N9—N10—H10 | 119.6 |
C2—C3—C4 | 119.0 (3) | O12—C11—N10 | 123.7 (3) |
C2—C3—H3 | 120.5 | O12—C11—C13 | 121.4 (3) |
C4—C3—H3 | 120.5 | N10—C11—C13 | 115.0 (2) |
C3—C4—C5 | 121.1 (3) | C14—C13—C18 | 117.2 (3) |
C3—C4—H4 | 119.4 | C14—C13—C11 | 123.3 (3) |
C5—C4—H4 | 119.4 | C18—C13—C11 | 119.5 (3) |
C4—C5—C6 | 118.2 (3) | C13—C14—C15 | 119.3 (3) |
C4—C5—C8 | 118.7 (3) | C13—C14—H14 | 120.4 |
C6—C5—C8 | 123.1 (3) | C15—C14—H14 | 120.4 |
C7—C6—C5 | 121.1 (3) | N16—C15—C14 | 123.8 (3) |
C7—C6—H6 | 119.5 | N16—C15—H15 | 118.1 |
C5—C6—H6 | 119.5 | C14—C15—H15 | 118.1 |
C6—C7—C2 | 119.3 (3) | C17—N16—C15 | 116.4 (3) |
C6—C7—H7 | 120.3 | N16—C17—C18 | 123.9 (3) |
C2—C7—H7 | 120.3 | N16—C17—H17 | 118.1 |
N9—C8—C5 | 122.9 (3) | C18—C17—H17 | 118.1 |
N9—C8—H8 | 118.5 | C17—C18—C13 | 119.4 (3) |
C5—C8—H8 | 118.5 | C17—C18—H18 | 120.3 |
C8—N9—N10 | 114.3 (3) | C13—C18—H18 | 120.3 |
| | | |
C7—C2—C3—C4 | 0.9 (6) | N9—N10—C11—O12 | 0.7 (5) |
Br1—C2—C3—C4 | −177.9 (3) | N9—N10—C11—C13 | −178.2 (3) |
C2—C3—C4—C5 | 1.0 (5) | O12—C11—C13—C14 | −150.8 (3) |
C3—C4—C5—C6 | −2.0 (5) | N10—C11—C13—C14 | 28.2 (4) |
C3—C4—C5—C8 | 177.6 (3) | O12—C11—C13—C18 | 27.0 (5) |
C4—C5—C6—C7 | 1.1 (5) | N10—C11—C13—C18 | −154.1 (3) |
C8—C5—C6—C7 | −178.5 (3) | C18—C13—C14—C15 | −0.4 (5) |
C5—C6—C7—C2 | 0.7 (5) | C11—C13—C14—C15 | 177.3 (3) |
C3—C2—C7—C6 | −1.8 (6) | C13—C14—C15—N16 | 1.8 (6) |
Br1—C2—C7—C6 | 177.0 (3) | C14—C15—N16—C17 | −1.4 (6) |
C4—C5—C8—N9 | 164.9 (3) | C15—N16—C17—C18 | −0.3 (6) |
C6—C5—C8—N9 | −15.4 (5) | N16—C17—C18—C13 | 1.6 (6) |
C5—C8—N9—N10 | −179.9 (3) | C14—C13—C18—C17 | −1.1 (5) |
C8—N9—N10—C11 | 174.1 (3) | C11—C13—C18—C17 | −179.0 (3) |
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