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The structures of the 18-membered diselenide-linked macrocycle 10,27-di-
tert-butyl 11,28-dioxo-2,3,19,20-tetraselena-10,12,27,29-tetraazapentacyclo[28.4.0.0
4,9.0
13,18.0
21,26]tetratriaconta-1(30),4(9),5,7,13,15,17,21,23,25,31,33-dodecaene-10,27-dicarboxylate, C
36H
34N
4O
6Se
4, and its precursor di-
tert-butyl 2,2′-[diselane-1,2-diylbis(2,1-phenylene)]dicarbamate, C
22H
28N
2O
4Se
2, are reported. The precusor to the macrocycle contains two
tert-butyl phenylcarbamate arms connected to a diselenide group, with Se—C and Se—Se bond lengths of 1.914 (4) and 2.3408 (6) Å, respectively. The macrocycle resides on a crystallographic center of inversion in space group
P with one molecule in the unit cell (
Z′ =
). It contains an 18-membered macrocyclic ring with two diselenide linkages. In this macrocycle, there are two free and two protected amino groups.
Supporting information
CCDC references: 1897283; 1897282
For both structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015). Program(s) used to solve structure: SHELXT (Sheldrick, 2015a) for (3); SHELXT2014 (Sheldrick, 2015a) for (4). For both structures, program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b). Molecular graphics: SHELXTL (Sheldrick, 2008) for (3); OLEX2 (Dolomanov et al., 2009) for (4). Software used to prepare material for publication: SHELXTL (Sheldrick, 2008) for (3); OLEX2 (Dolomanov et al., 2009) for (4).
Di-
tert-butyl 2,2'-[diselane-1,2-diylbis(2,1-phenylene)]dicarbamate (3)
top
Crystal data top
C22H28N2O4Se2 | F(000) = 2192 |
Mr = 542.38 | Dx = 1.489 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 18.1780 (7) Å | Cell parameters from 9904 reflections |
b = 9.3386 (5) Å | θ = 2.5–29.7° |
c = 28.9009 (18) Å | µ = 3.08 mm−1 |
β = 99.440 (5)° | T = 100 K |
V = 4839.7 (4) Å3 | Prism, colourless |
Z = 8 | 0.16 × 0.10 × 0.09 mm |
Data collection top
Rigaku CCD dual source diffractometer | 4483 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.079 |
ω scans | θmax = 27.9°, θmin = 2.5° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)' | h = −23→23 |
Tmin = 0.754, Tmax = 1.000 | k = −12→12 |
37302 measured reflections | l = −38→36 |
5769 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.0295P)2 + 17.3868P] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max = 0.001 |
5769 reflections | Δρmax = 0.85 e Å−3 |
285 parameters | Δρmin = −0.67 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 | |
Se1 | 0.86339 (2) | 0.28216 (4) | 0.49219 (2) | 0.02931 (11) | |
Se2 | 0.86311 (2) | 0.52389 (4) | 0.51358 (2) | 0.03443 (12) | |
N1 | 0.74970 (17) | 0.2863 (4) | 0.39781 (13) | 0.0306 (7) | |
H1N | 0.746 (2) | 0.290 (4) | 0.4251 (15) | 0.031 (12)* | |
O2 | 0.68533 (16) | 0.2820 (4) | 0.32374 (11) | 0.0510 (9) | |
O3 | 0.62763 (14) | 0.2820 (4) | 0.38685 (10) | 0.0410 (7) | |
N2 | 0.74455 (19) | 0.6127 (4) | 0.42843 (12) | 0.0293 (7) | |
H2N | 0.787 (2) | 0.592 (5) | 0.4328 (15) | 0.035 (13)* | |
O5 | 0.65091 (15) | 0.7150 (4) | 0.37732 (11) | 0.0467 (8) | |
O6 | 0.76644 (14) | 0.6826 (3) | 0.36002 (9) | 0.0346 (7) | |
C1 | 0.8811 (2) | 0.2945 (4) | 0.42882 (14) | 0.0276 (8) | |
C2 | 0.9546 (2) | 0.2980 (5) | 0.42168 (16) | 0.0380 (10) | |
H2A | 0.993426 | 0.300576 | 0.448064 | 0.046* | |
C3 | 0.9728 (2) | 0.2978 (5) | 0.37751 (17) | 0.0451 (11) | |
H3A | 1.023413 | 0.299498 | 0.373123 | 0.054* | |
C4 | 0.9161 (2) | 0.2950 (5) | 0.33972 (17) | 0.0466 (11) | |
H4A | 0.928125 | 0.295193 | 0.308944 | 0.056* | |
C5 | 0.8425 (2) | 0.2918 (5) | 0.34533 (15) | 0.0381 (10) | |
H5A | 0.804348 | 0.289842 | 0.318596 | 0.046* | |
C6 | 0.8238 (2) | 0.2915 (4) | 0.39029 (14) | 0.0293 (8) | |
C7 | 0.6869 (2) | 0.2829 (4) | 0.36527 (15) | 0.0309 (9) | |
C8 | 0.5517 (2) | 0.2720 (5) | 0.35906 (14) | 0.0372 (10) | |
C9 | 0.5444 (3) | 0.1363 (6) | 0.3312 (2) | 0.0604 (15) | |
H9A | 0.561861 | 0.055707 | 0.351834 | 0.091* | |
H9B | 0.574485 | 0.143015 | 0.306137 | 0.091* | |
H9C | 0.491961 | 0.121370 | 0.317512 | 0.091* | |
C10 | 0.5039 (2) | 0.2680 (8) | 0.39657 (18) | 0.075 (2) | |
H10A | 0.515967 | 0.182433 | 0.415966 | 0.113* | |
H10B | 0.451279 | 0.265243 | 0.382103 | 0.113* | |
H10C | 0.513294 | 0.353716 | 0.416221 | 0.113* | |
C11 | 0.5361 (3) | 0.4024 (6) | 0.3290 (2) | 0.0595 (15) | |
H11A | 0.549311 | 0.488165 | 0.348096 | 0.089* | |
H11B | 0.482952 | 0.405413 | 0.315638 | 0.089* | |
H11C | 0.565753 | 0.398961 | 0.303626 | 0.089* | |
C12 | 0.7578 (2) | 0.5542 (4) | 0.51048 (14) | 0.0302 (9) | |
C13 | 0.7281 (3) | 0.5382 (4) | 0.55114 (14) | 0.0360 (10) | |
H13A | 0.759977 | 0.513769 | 0.579473 | 0.043* | |
C14 | 0.6534 (3) | 0.5570 (4) | 0.55131 (15) | 0.0383 (10) | |
H14A | 0.633408 | 0.545968 | 0.579479 | 0.046* | |
C15 | 0.6077 (2) | 0.5921 (4) | 0.50989 (16) | 0.0382 (10) | |
H15A | 0.555700 | 0.604075 | 0.509593 | 0.046* | |
C16 | 0.6364 (2) | 0.6102 (4) | 0.46876 (15) | 0.0323 (9) | |
H16A | 0.604120 | 0.634318 | 0.440563 | 0.039* | |
C17 | 0.7124 (2) | 0.5931 (4) | 0.46861 (14) | 0.0290 (9) | |
C18 | 0.7138 (2) | 0.6745 (4) | 0.38731 (14) | 0.0295 (8) | |
C19 | 0.7477 (2) | 0.7340 (5) | 0.31132 (14) | 0.0355 (10) | |
C20 | 0.8205 (3) | 0.7129 (6) | 0.29334 (16) | 0.0550 (14) | |
H20A | 0.835116 | 0.611875 | 0.296517 | 0.083* | |
H20B | 0.859253 | 0.772179 | 0.311612 | 0.083* | |
H20C | 0.814250 | 0.740755 | 0.260242 | 0.083* | |
C21 | 0.7267 (3) | 0.8899 (5) | 0.31093 (19) | 0.0631 (15) | |
H21A | 0.765875 | 0.943841 | 0.330904 | 0.095* | |
H21B | 0.679515 | 0.900699 | 0.322864 | 0.095* | |
H21C | 0.720857 | 0.926599 | 0.278774 | 0.095* | |
C22 | 0.6876 (3) | 0.6411 (6) | 0.28424 (16) | 0.0532 (13) | |
H22A | 0.700412 | 0.540007 | 0.289997 | 0.080* | |
H22B | 0.683372 | 0.661512 | 0.250650 | 0.080* | |
H22C | 0.639848 | 0.661397 | 0.294502 | 0.080* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Se1 | 0.02644 (19) | 0.0251 (2) | 0.0347 (2) | −0.00019 (17) | 0.00028 (16) | 0.00124 (16) |
Se2 | 0.0314 (2) | 0.0263 (2) | 0.0424 (3) | −0.00377 (18) | −0.00323 (17) | −0.00391 (18) |
N1 | 0.0198 (15) | 0.042 (2) | 0.030 (2) | −0.0002 (15) | 0.0044 (14) | −0.0020 (16) |
O2 | 0.0267 (15) | 0.094 (3) | 0.0324 (18) | −0.0036 (17) | 0.0032 (13) | −0.0010 (17) |
O3 | 0.0173 (13) | 0.072 (2) | 0.0334 (16) | 0.0013 (14) | 0.0022 (11) | −0.0041 (15) |
N2 | 0.0235 (17) | 0.0331 (19) | 0.0318 (19) | 0.0034 (15) | 0.0056 (15) | 0.0041 (14) |
O5 | 0.0264 (15) | 0.070 (2) | 0.0454 (18) | 0.0156 (15) | 0.0113 (13) | 0.0166 (16) |
O6 | 0.0245 (14) | 0.0505 (18) | 0.0299 (15) | 0.0035 (13) | 0.0078 (11) | 0.0058 (13) |
C1 | 0.0234 (18) | 0.0197 (18) | 0.039 (2) | 0.0009 (16) | 0.0031 (16) | −0.0003 (16) |
C2 | 0.0208 (19) | 0.038 (2) | 0.053 (3) | −0.0045 (18) | 0.0007 (18) | 0.002 (2) |
C3 | 0.025 (2) | 0.053 (3) | 0.060 (3) | 0.000 (2) | 0.016 (2) | 0.007 (2) |
C4 | 0.037 (2) | 0.062 (3) | 0.044 (3) | 0.002 (2) | 0.017 (2) | 0.003 (2) |
C5 | 0.027 (2) | 0.050 (3) | 0.038 (2) | −0.002 (2) | 0.0073 (18) | −0.006 (2) |
C6 | 0.0214 (18) | 0.028 (2) | 0.039 (2) | −0.0008 (16) | 0.0058 (16) | −0.0028 (17) |
C7 | 0.0217 (18) | 0.034 (2) | 0.037 (2) | 0.0027 (17) | 0.0057 (16) | −0.0009 (18) |
C8 | 0.0176 (18) | 0.059 (3) | 0.034 (2) | −0.0003 (19) | 0.0001 (16) | 0.000 (2) |
C9 | 0.030 (2) | 0.058 (3) | 0.089 (4) | −0.009 (2) | 0.001 (3) | −0.014 (3) |
C10 | 0.018 (2) | 0.165 (7) | 0.043 (3) | 0.002 (3) | 0.004 (2) | 0.002 (3) |
C11 | 0.030 (2) | 0.057 (3) | 0.088 (4) | 0.005 (2) | −0.002 (3) | 0.015 (3) |
C12 | 0.037 (2) | 0.0147 (18) | 0.038 (2) | −0.0009 (16) | 0.0048 (18) | −0.0043 (16) |
C13 | 0.053 (3) | 0.023 (2) | 0.032 (2) | 0.000 (2) | 0.006 (2) | −0.0033 (16) |
C14 | 0.058 (3) | 0.0196 (19) | 0.042 (3) | 0.0012 (19) | 0.022 (2) | −0.0016 (17) |
C15 | 0.035 (2) | 0.028 (2) | 0.056 (3) | −0.0005 (18) | 0.020 (2) | −0.0040 (19) |
C16 | 0.032 (2) | 0.0209 (19) | 0.045 (2) | −0.0003 (17) | 0.0120 (19) | 0.0010 (17) |
C17 | 0.034 (2) | 0.0165 (17) | 0.037 (2) | −0.0007 (16) | 0.0092 (18) | −0.0017 (15) |
C18 | 0.029 (2) | 0.030 (2) | 0.031 (2) | −0.0005 (17) | 0.0089 (17) | −0.0016 (16) |
C19 | 0.030 (2) | 0.050 (3) | 0.027 (2) | −0.0024 (19) | 0.0038 (17) | 0.0101 (19) |
C20 | 0.039 (3) | 0.092 (4) | 0.036 (3) | −0.004 (3) | 0.012 (2) | 0.008 (3) |
C21 | 0.082 (4) | 0.051 (3) | 0.062 (3) | 0.013 (3) | 0.028 (3) | 0.021 (3) |
C22 | 0.043 (3) | 0.079 (4) | 0.035 (3) | −0.012 (3) | 0.001 (2) | 0.007 (3) |
Geometric parameters (Å, º) top
Se1—C1 | 1.914 (4) | C9—H9C | 0.9800 |
Se1—Se2 | 2.3408 (6) | C10—H10A | 0.9800 |
Se2—C12 | 1.923 (4) | C10—H10B | 0.9800 |
N1—C7 | 1.356 (5) | C10—H10C | 0.9800 |
N1—C6 | 1.399 (5) | C11—H11A | 0.9800 |
N1—H1N | 0.80 (4) | C11—H11B | 0.9800 |
O2—C7 | 1.196 (5) | C11—H11C | 0.9800 |
O3—C7 | 1.330 (5) | C12—C13 | 1.379 (6) |
O3—C8 | 1.482 (4) | C12—C17 | 1.396 (6) |
N2—C18 | 1.356 (5) | C13—C14 | 1.370 (6) |
N2—C17 | 1.395 (5) | C13—H13A | 0.9500 |
N2—H2N | 0.79 (4) | C14—C15 | 1.380 (6) |
O5—C18 | 1.194 (5) | C14—H14A | 0.9500 |
O6—C18 | 1.338 (4) | C15—C16 | 1.385 (6) |
O6—C19 | 1.473 (5) | C15—H15A | 0.9500 |
C1—C2 | 1.386 (5) | C16—C17 | 1.392 (5) |
C1—C6 | 1.395 (5) | C16—H16A | 0.9500 |
C2—C3 | 1.370 (6) | C19—C21 | 1.504 (6) |
C2—H2A | 0.9500 | C19—C22 | 1.511 (6) |
C3—C4 | 1.373 (6) | C19—C20 | 1.511 (6) |
C3—H3A | 0.9500 | C20—H20A | 0.9800 |
C4—C5 | 1.375 (6) | C20—H20B | 0.9800 |
C4—H4A | 0.9500 | C20—H20C | 0.9800 |
C5—C6 | 1.396 (6) | C21—H21A | 0.9800 |
C5—H5A | 0.9500 | C21—H21B | 0.9800 |
C8—C9 | 1.495 (7) | C21—H21C | 0.9800 |
C8—C11 | 1.495 (6) | C22—H22A | 0.9800 |
C8—C10 | 1.496 (6) | C22—H22B | 0.9800 |
C9—H9A | 0.9800 | C22—H22C | 0.9800 |
C9—H9B | 0.9800 | | |
| | | |
C1—Se1—Se2 | 101.68 (11) | C8—C11—H11B | 109.5 |
C12—Se2—Se1 | 100.07 (11) | H11A—C11—H11B | 109.5 |
C7—N1—C6 | 128.0 (4) | C8—C11—H11C | 109.5 |
C7—N1—H1N | 120 (3) | H11A—C11—H11C | 109.5 |
C6—N1—H1N | 112 (3) | H11B—C11—H11C | 109.5 |
C7—O3—C8 | 120.0 (3) | C13—C12—C17 | 120.6 (4) |
C18—N2—C17 | 128.1 (3) | C13—C12—Se2 | 118.0 (3) |
C18—N2—H2N | 120 (3) | C17—C12—Se2 | 121.4 (3) |
C17—N2—H2N | 112 (3) | C14—C13—C12 | 121.0 (4) |
C18—O6—C19 | 120.4 (3) | C14—C13—H13A | 119.5 |
C2—C1—C6 | 119.6 (4) | C12—C13—H13A | 119.5 |
C2—C1—Se1 | 117.5 (3) | C13—C14—C15 | 118.9 (4) |
C6—C1—Se1 | 122.8 (3) | C13—C14—H14A | 120.5 |
C3—C2—C1 | 121.6 (4) | C15—C14—H14A | 120.5 |
C3—C2—H2A | 119.2 | C14—C15—C16 | 121.0 (4) |
C1—C2—H2A | 119.2 | C14—C15—H15A | 119.5 |
C2—C3—C4 | 118.6 (4) | C16—C15—H15A | 119.5 |
C2—C3—H3A | 120.7 | C15—C16—C17 | 120.2 (4) |
C4—C3—H3A | 120.7 | C15—C16—H16A | 119.9 |
C3—C4—C5 | 121.6 (4) | C17—C16—H16A | 119.9 |
C3—C4—H4A | 119.2 | C16—C17—N2 | 122.6 (4) |
C5—C4—H4A | 119.2 | C16—C17—C12 | 118.2 (4) |
C4—C5—C6 | 120.0 (4) | N2—C17—C12 | 119.2 (4) |
C4—C5—H5A | 120.0 | O5—C18—O6 | 126.1 (4) |
C6—C5—H5A | 120.0 | O5—C18—N2 | 125.9 (4) |
C1—C6—C5 | 118.6 (3) | O6—C18—N2 | 108.0 (3) |
C1—C6—N1 | 119.3 (4) | O6—C19—C21 | 110.0 (4) |
C5—C6—N1 | 122.2 (4) | O6—C19—C22 | 110.0 (3) |
O2—C7—O3 | 125.7 (4) | C21—C19—C22 | 113.0 (4) |
O2—C7—N1 | 125.1 (4) | O6—C19—C20 | 102.0 (3) |
O3—C7—N1 | 109.2 (3) | C21—C19—C20 | 111.1 (4) |
O3—C8—C9 | 109.7 (4) | C22—C19—C20 | 110.3 (4) |
O3—C8—C11 | 109.5 (4) | C19—C20—H20A | 109.5 |
C9—C8—C11 | 112.7 (4) | C19—C20—H20B | 109.5 |
O3—C8—C10 | 102.0 (3) | H20A—C20—H20B | 109.5 |
C9—C8—C10 | 111.0 (5) | C19—C20—H20C | 109.5 |
C11—C8—C10 | 111.4 (4) | H20A—C20—H20C | 109.5 |
C8—C9—H9A | 109.5 | H20B—C20—H20C | 109.5 |
C8—C9—H9B | 109.5 | C19—C21—H21A | 109.5 |
H9A—C9—H9B | 109.5 | C19—C21—H21B | 109.5 |
C8—C9—H9C | 109.5 | H21A—C21—H21B | 109.5 |
H9A—C9—H9C | 109.5 | C19—C21—H21C | 109.5 |
H9B—C9—H9C | 109.5 | H21A—C21—H21C | 109.5 |
C8—C10—H10A | 109.5 | H21B—C21—H21C | 109.5 |
C8—C10—H10B | 109.5 | C19—C22—H22A | 109.5 |
H10A—C10—H10B | 109.5 | C19—C22—H22B | 109.5 |
C8—C10—H10C | 109.5 | H22A—C22—H22B | 109.5 |
H10A—C10—H10C | 109.5 | C19—C22—H22C | 109.5 |
H10B—C10—H10C | 109.5 | H22A—C22—H22C | 109.5 |
C8—C11—H11A | 109.5 | H22B—C22—H22C | 109.5 |
| | | |
C6—C1—C2—C3 | −0.3 (6) | C17—C12—C13—C14 | 1.4 (6) |
Se1—C1—C2—C3 | 175.9 (3) | Se2—C12—C13—C14 | −179.4 (3) |
C1—C2—C3—C4 | 0.4 (7) | C12—C13—C14—C15 | 0.2 (6) |
C2—C3—C4—C5 | −0.3 (8) | C13—C14—C15—C16 | −0.8 (6) |
C3—C4—C5—C6 | 0.0 (7) | C14—C15—C16—C17 | 0.0 (6) |
C2—C1—C6—C5 | 0.1 (6) | C15—C16—C17—N2 | −178.7 (4) |
Se1—C1—C6—C5 | −175.9 (3) | C15—C16—C17—C12 | 1.5 (5) |
C2—C1—C6—N1 | 179.3 (4) | C18—N2—C17—C16 | 13.4 (6) |
Se1—C1—C6—N1 | 3.3 (5) | C18—N2—C17—C12 | −166.9 (4) |
C4—C5—C6—C1 | 0.1 (6) | C13—C12—C17—C16 | −2.2 (5) |
C4—C5—C6—N1 | −179.1 (4) | Se2—C12—C17—C16 | 178.6 (3) |
C7—N1—C6—C1 | 179.9 (4) | C13—C12—C17—N2 | 178.0 (3) |
C7—N1—C6—C5 | −0.9 (7) | Se2—C12—C17—N2 | −1.2 (5) |
C8—O3—C7—O2 | 3.3 (7) | C19—O6—C18—O5 | −5.4 (6) |
C8—O3—C7—N1 | −177.3 (4) | C19—O6—C18—N2 | 174.8 (3) |
C6—N1—C7—O2 | 0.9 (7) | C17—N2—C18—O5 | −5.4 (7) |
C6—N1—C7—O3 | −178.5 (4) | C17—N2—C18—O6 | 174.4 (4) |
C7—O3—C8—C9 | 59.9 (5) | C18—O6—C19—C21 | 66.8 (5) |
C7—O3—C8—C11 | −64.3 (5) | C18—O6—C19—C22 | −58.3 (5) |
C7—O3—C8—C10 | 177.6 (4) | C18—O6—C19—C20 | −175.3 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···Se1 | 0.80 (4) | 2.63 (4) | 3.141 (3) | 123 (4) |
N2—H2N···Se2 | 0.79 (4) | 2.59 (4) | 3.106 (3) | 125 (4) |
C2—H2A···Se2i | 0.95 | 3.13 | 3.900 (4) | 140 |
C5—H5A···O2 | 0.95 | 2.19 | 2.824 (5) | 123 |
C9—H9B···O2 | 0.98 | 2.38 | 2.941 (6) | 116 |
C10—H10A···Se1ii | 0.98 | 3.17 | 3.719 (5) | 117 |
C11—H11C···O2 | 0.98 | 2.42 | 2.964 (6) | 115 |
C16—H16A···O5 | 0.95 | 2.27 | 2.871 (5) | 121 |
C20—H20C···O2iii | 0.98 | 2.46 | 3.429 (6) | 171 |
C21—H21B···O5 | 0.98 | 2.45 | 3.019 (6) | 116 |
C22—H22A···O2 | 0.98 | 2.63 | 3.544 (7) | 155 |
C22—H22C···O5 | 0.98 | 2.42 | 2.957 (6) | 114 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+3/2, −y+1/2, −z+1; (iii) −x+3/2, y+1/2, −z+1/2. |
10,27-Di-
tert-butyl 11,28-dioxo-2,3,19,20-tetraselena-10,12,27,29-tetraazapentacyclo[28.4.0.0
4,9.0
13,18.0
21,26]tetratriaconta-1(30),4(9),5,7,13,15,17,21,23,25,31,33-dodecaene-10,27-dicarboxylate (4)
top
Crystal data top
C36H34N4O6Se4 | Z = 1 |
Mr = 934.51 | F(000) = 462 |
Triclinic, P1 | Dx = 1.704 Mg m−3 |
a = 9.4865 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.7410 (2) Å | Cell parameters from 15479 reflections |
c = 11.2789 (3) Å | θ = 2.4–31.3° |
α = 101.000 (2)° | µ = 4.08 mm−1 |
β = 108.394 (2)° | T = 100 K |
γ = 105.264 (2)° | Needle, clear intense orange |
V = 910.42 (4) Å3 | 0.17 × 0.16 × 0.11 mm |
Data collection top
Rigaku CCD dual source diffractometer | 4766 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.037 |
ω scans | θmax = 31.2°, θmin = 2.4° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −13→13 |
Tmin = 0.823, Tmax = 1.000 | k = −14→14 |
23930 measured reflections | l = −16→15 |
5406 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.026 | All H-atom parameters refined |
wR(F2) = 0.065 | w = 1/[σ2(Fo2) + (0.0337P)2 + 0.3223P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
5406 reflections | Δρmax = 0.69 e Å−3 |
294 parameters | Δρmin = −0.47 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 | |
Se1 | 0.04380 (2) | 0.49656 (2) | 0.30624 (2) | 0.02120 (5) | |
Se2 | 0.20175 (2) | 0.43386 (2) | 0.47712 (2) | 0.02078 (5) | |
O1 | 0.62718 (14) | 0.68582 (15) | 0.30763 (12) | 0.0268 (3) | |
O2 | 0.39283 (14) | 0.78120 (14) | 0.54761 (12) | 0.0245 (3) | |
O3 | 0.63606 (14) | 0.85044 (14) | 0.70736 (11) | 0.0236 (2) | |
N1 | 0.38224 (16) | 0.65545 (16) | 0.31384 (14) | 0.0212 (3) | |
H1 | 0.341 (3) | 0.677 (2) | 0.364 (2) | 0.028 (6)* | |
N2 | 0.61486 (15) | 0.79034 (15) | 0.50056 (13) | 0.0188 (3) | |
C1 | 0.13119 (19) | 0.46199 (18) | 0.17561 (16) | 0.0206 (3) | |
C2 | 0.0308 (2) | 0.3550 (2) | 0.05685 (18) | 0.0254 (3) | |
H2 | −0.070 (2) | 0.298 (2) | 0.052 (2) | 0.025 (5)* | |
C3 | 0.0783 (2) | 0.3337 (2) | −0.04709 (18) | 0.0292 (4) | |
H3 | 0.006 (3) | 0.266 (3) | −0.126 (2) | 0.038 (6)* | |
C4 | 0.2278 (2) | 0.4198 (2) | −0.03280 (18) | 0.0289 (4) | |
H4 | 0.257 (3) | 0.413 (2) | −0.099 (2) | 0.029 (6)* | |
C5 | 0.3309 (2) | 0.5270 (2) | 0.08602 (18) | 0.0254 (3) | |
H5 | 0.427 (3) | 0.587 (2) | 0.095 (2) | 0.030 (6)* | |
C6 | 0.28439 (19) | 0.54868 (18) | 0.19161 (16) | 0.0200 (3) | |
C7 | 0.54289 (18) | 0.70675 (18) | 0.36558 (16) | 0.0192 (3) | |
C8 | 0.78540 (18) | 0.86088 (18) | 0.55745 (15) | 0.0191 (3) | |
C9 | 0.88618 (18) | 0.78022 (18) | 0.58540 (16) | 0.0190 (3) | |
C10 | 1.0487 (2) | 0.8571 (2) | 0.65130 (18) | 0.0246 (3) | |
H10 | 1.115 (2) | 0.803 (2) | 0.668 (2) | 0.023 (5)* | |
C11 | 1.1079 (2) | 1.0112 (2) | 0.68627 (18) | 0.0259 (4) | |
H11 | 1.216 (3) | 1.063 (3) | 0.728 (2) | 0.040 (6)* | |
C12 | 1.0078 (2) | 1.0906 (2) | 0.65271 (17) | 0.0241 (3) | |
H12 | 1.048 (2) | 1.191 (2) | 0.666 (2) | 0.025 (5)* | |
C13 | 0.8458 (2) | 1.01533 (19) | 0.58854 (17) | 0.0221 (3) | |
H13 | 0.776 (2) | 1.067 (2) | 0.564 (2) | 0.021 (5)* | |
C14 | 0.53423 (19) | 0.80575 (18) | 0.58434 (16) | 0.0193 (3) | |
C15 | 0.5869 (2) | 0.8912 (2) | 0.81793 (17) | 0.0239 (3) | |
C16 | 0.7421 (3) | 0.9359 (3) | 0.9349 (2) | 0.0343 (4) | |
H16A | 0.734 (3) | 0.967 (3) | 1.013 (3) | 0.043 (7)* | |
H16C | 0.813 (3) | 1.004 (3) | 0.926 (2) | 0.042 (7)* | |
C17 | 0.5305 (3) | 1.0216 (3) | 0.8070 (2) | 0.0378 (5) | |
H17A | 0.608 (3) | 1.099 (3) | 0.801 (2) | 0.033 (6)* | |
H17B | 0.436 (3) | 0.997 (3) | 0.726 (3) | 0.039 (6)* | |
H17C | 0.514 (4) | 1.044 (3) | 0.883 (3) | 0.063 (9)* | |
C18 | 0.4628 (3) | 0.7560 (3) | 0.8179 (2) | 0.0353 (4) | |
H18A | 0.447 (3) | 0.781 (3) | 0.896 (3) | 0.055 (8)* | |
H18B | 0.361 (3) | 0.723 (3) | 0.744 (3) | 0.044 (7)* | |
H18C | 0.501 (3) | 0.673 (3) | 0.814 (3) | 0.054 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Se1 | 0.01818 (8) | 0.02274 (9) | 0.02408 (9) | 0.00897 (6) | 0.00741 (6) | 0.00874 (7) |
Se2 | 0.02023 (8) | 0.01904 (9) | 0.02065 (9) | 0.00580 (6) | 0.00545 (6) | 0.00628 (6) |
O1 | 0.0208 (6) | 0.0346 (7) | 0.0212 (6) | 0.0060 (5) | 0.0097 (5) | 0.0026 (5) |
O2 | 0.0186 (5) | 0.0307 (7) | 0.0229 (6) | 0.0104 (5) | 0.0076 (5) | 0.0039 (5) |
O3 | 0.0214 (5) | 0.0324 (7) | 0.0178 (6) | 0.0116 (5) | 0.0076 (5) | 0.0058 (5) |
N1 | 0.0178 (6) | 0.0256 (7) | 0.0176 (6) | 0.0061 (5) | 0.0062 (5) | 0.0035 (6) |
N2 | 0.0157 (6) | 0.0206 (6) | 0.0178 (6) | 0.0051 (5) | 0.0059 (5) | 0.0038 (5) |
C1 | 0.0204 (7) | 0.0211 (7) | 0.0200 (7) | 0.0084 (6) | 0.0053 (6) | 0.0076 (6) |
C2 | 0.0226 (8) | 0.0225 (8) | 0.0253 (9) | 0.0078 (7) | 0.0032 (7) | 0.0050 (7) |
C3 | 0.0326 (9) | 0.0256 (9) | 0.0202 (8) | 0.0109 (7) | 0.0018 (7) | −0.0002 (7) |
C4 | 0.0336 (9) | 0.0355 (10) | 0.0186 (8) | 0.0166 (8) | 0.0085 (7) | 0.0064 (7) |
C5 | 0.0238 (8) | 0.0317 (9) | 0.0211 (8) | 0.0114 (7) | 0.0075 (7) | 0.0084 (7) |
C6 | 0.0201 (7) | 0.0209 (7) | 0.0174 (7) | 0.0080 (6) | 0.0038 (6) | 0.0063 (6) |
C7 | 0.0190 (7) | 0.0188 (7) | 0.0187 (7) | 0.0055 (6) | 0.0056 (6) | 0.0070 (6) |
C8 | 0.0162 (7) | 0.0210 (8) | 0.0167 (7) | 0.0035 (6) | 0.0053 (6) | 0.0044 (6) |
C9 | 0.0183 (7) | 0.0186 (7) | 0.0192 (7) | 0.0044 (6) | 0.0071 (6) | 0.0063 (6) |
C10 | 0.0190 (7) | 0.0282 (9) | 0.0258 (9) | 0.0077 (7) | 0.0068 (7) | 0.0101 (7) |
C11 | 0.0185 (7) | 0.0280 (9) | 0.0237 (8) | 0.0003 (7) | 0.0055 (7) | 0.0069 (7) |
C12 | 0.0258 (8) | 0.0209 (8) | 0.0206 (8) | 0.0019 (7) | 0.0093 (7) | 0.0033 (7) |
C13 | 0.0240 (8) | 0.0220 (8) | 0.0211 (8) | 0.0087 (6) | 0.0098 (6) | 0.0056 (7) |
C14 | 0.0203 (7) | 0.0187 (7) | 0.0193 (7) | 0.0082 (6) | 0.0076 (6) | 0.0048 (6) |
C15 | 0.0291 (8) | 0.0270 (8) | 0.0188 (8) | 0.0117 (7) | 0.0120 (7) | 0.0060 (7) |
C16 | 0.0335 (10) | 0.0429 (12) | 0.0188 (9) | 0.0087 (9) | 0.0062 (8) | 0.0053 (8) |
C17 | 0.0512 (13) | 0.0359 (11) | 0.0330 (11) | 0.0271 (11) | 0.0165 (10) | 0.0078 (9) |
C18 | 0.0383 (11) | 0.0388 (11) | 0.0299 (10) | 0.0085 (9) | 0.0178 (9) | 0.0118 (9) |
Geometric parameters (Å, º) top
Se1—C1 | 1.9235 (17) | C5—H5 | 0.91 (2) |
Se1—Se2 | 2.3327 (2) | C8—C9 | 1.389 (2) |
Se2—C9i | 1.9219 (16) | C8—C13 | 1.390 (2) |
O1—C7 | 1.214 (2) | C9—C10 | 1.395 (2) |
O2—C14 | 1.2128 (19) | C10—C11 | 1.384 (3) |
O3—C14 | 1.323 (2) | C10—H10 | 0.92 (2) |
O3—C15 | 1.486 (2) | C11—C12 | 1.384 (3) |
N1—C7 | 1.356 (2) | C11—H11 | 0.93 (2) |
N1—C6 | 1.407 (2) | C12—C13 | 1.388 (2) |
N1—H1 | 0.81 (2) | C12—H12 | 0.92 (2) |
N2—C14 | 1.401 (2) | C13—H13 | 0.94 (2) |
N2—C7 | 1.423 (2) | C15—C17 | 1.513 (3) |
N2—C8 | 1.4465 (19) | C15—C18 | 1.518 (3) |
C1—C2 | 1.388 (2) | C15—C16 | 1.522 (3) |
C1—C6 | 1.410 (2) | C16—H16A | 0.91 (3) |
C2—C3 | 1.382 (3) | C16—H16C | 0.85 (3) |
C2—H2 | 0.95 (2) | C17—H17A | 0.93 (2) |
C3—C4 | 1.385 (3) | C17—H17B | 0.99 (3) |
C3—H3 | 0.92 (2) | C17—H17C | 0.92 (3) |
C4—C5 | 1.394 (3) | C18—H18A | 0.94 (3) |
C4—H4 | 0.87 (2) | C18—H18B | 0.98 (3) |
C5—C6 | 1.394 (2) | C18—H18C | 0.96 (3) |
| | | |
C1—Se1—Se2 | 102.63 (5) | C11—C10—C9 | 120.19 (16) |
C9i—Se2—Se1 | 101.30 (5) | C11—C10—H10 | 121.4 (13) |
C14—O3—C15 | 121.28 (13) | C9—C10—H10 | 118.4 (13) |
C7—N1—C6 | 125.87 (15) | C12—C11—C10 | 120.59 (16) |
C7—N1—H1 | 115.5 (16) | C12—C11—H11 | 118.4 (15) |
C6—N1—H1 | 117.5 (16) | C10—C11—H11 | 120.9 (15) |
C14—N2—C7 | 125.19 (13) | C11—C12—C13 | 119.62 (17) |
C14—N2—C8 | 117.10 (13) | C11—C12—H12 | 120.8 (13) |
C7—N2—C8 | 117.67 (13) | C13—C12—H12 | 119.4 (13) |
C2—C1—C6 | 119.88 (16) | C12—C13—C8 | 119.86 (16) |
C2—C1—Se1 | 116.87 (13) | C12—C13—H13 | 121.2 (12) |
C6—C1—Se1 | 122.99 (12) | C8—C13—H13 | 118.9 (12) |
C3—C2—C1 | 120.76 (17) | O2—C14—O3 | 126.26 (15) |
C3—C2—H2 | 122.7 (13) | O2—C14—N2 | 124.34 (15) |
C1—C2—H2 | 116.5 (13) | O3—C14—N2 | 109.40 (13) |
C2—C3—C4 | 119.73 (17) | O3—C15—C17 | 108.43 (15) |
C2—C3—H3 | 118.1 (15) | O3—C15—C18 | 109.81 (15) |
C4—C3—H3 | 122.0 (15) | C17—C15—C18 | 113.42 (18) |
C3—C4—C5 | 120.40 (18) | O3—C15—C16 | 101.27 (14) |
C3—C4—H4 | 120.8 (15) | C17—C15—C16 | 111.86 (17) |
C5—C4—H4 | 118.6 (15) | C18—C15—C16 | 111.31 (17) |
C6—C5—C4 | 120.28 (17) | C15—C16—H16A | 113.0 (16) |
C6—C5—H5 | 118.9 (14) | C15—C16—H16C | 108.9 (17) |
C4—C5—H5 | 120.8 (14) | H16A—C16—H16C | 110 (2) |
C5—C6—N1 | 123.14 (15) | C15—C17—H17A | 110.0 (14) |
C5—C6—C1 | 118.94 (16) | C15—C17—H17B | 112.9 (14) |
N1—C6—C1 | 117.91 (15) | H17A—C17—H17B | 105 (2) |
O1—C7—N1 | 125.85 (16) | C15—C17—H17C | 101.4 (19) |
O1—C7—N2 | 118.81 (14) | H17A—C17—H17C | 113 (2) |
N1—C7—N2 | 115.33 (14) | H17B—C17—H17C | 115 (2) |
C9—C8—C13 | 120.65 (15) | C15—C18—H18A | 107.7 (17) |
C9—C8—N2 | 122.21 (14) | C15—C18—H18B | 113.9 (15) |
C13—C8—N2 | 117.10 (14) | H18A—C18—H18B | 109 (2) |
C8—C9—C10 | 118.97 (15) | C15—C18—H18C | 109.5 (17) |
C8—C9—Se2i | 118.80 (12) | H18A—C18—H18C | 110 (2) |
C10—C9—Se2i | 122.12 (13) | H18B—C18—H18C | 107 (2) |
| | | |
C6—C1—C2—C3 | −1.0 (3) | C7—N2—C8—C13 | 108.54 (17) |
Se1—C1—C2—C3 | 173.31 (14) | C13—C8—C9—C10 | 3.3 (2) |
C1—C2—C3—C4 | 0.0 (3) | N2—C8—C9—C10 | −174.09 (15) |
C2—C3—C4—C5 | 0.5 (3) | C13—C8—C9—Se2i | −173.12 (12) |
C3—C4—C5—C6 | −0.1 (3) | N2—C8—C9—Se2i | 9.5 (2) |
C4—C5—C6—N1 | −179.62 (16) | C8—C9—C10—C11 | −0.9 (3) |
C4—C5—C6—C1 | −0.8 (3) | Se2i—C9—C10—C11 | 175.31 (14) |
C7—N1—C6—C5 | −28.0 (3) | C9—C10—C11—C12 | −2.1 (3) |
C7—N1—C6—C1 | 153.19 (16) | C10—C11—C12—C13 | 2.9 (3) |
C2—C1—C6—C5 | 1.3 (2) | C11—C12—C13—C8 | −0.6 (3) |
Se1—C1—C6—C5 | −172.56 (13) | C9—C8—C13—C12 | −2.5 (3) |
C2—C1—C6—N1 | −179.79 (15) | N2—C8—C13—C12 | 174.96 (15) |
Se1—C1—C6—N1 | 6.3 (2) | C15—O3—C14—O2 | −6.4 (3) |
C6—N1—C7—O1 | 11.6 (3) | C15—O3—C14—N2 | 173.61 (13) |
C6—N1—C7—N2 | −167.49 (15) | C7—N2—C14—O2 | −18.5 (3) |
C14—N2—C7—O1 | −170.50 (15) | C8—N2—C14—O2 | 163.79 (16) |
C8—N2—C7—O1 | 7.2 (2) | C7—N2—C14—O3 | 161.44 (14) |
C14—N2—C7—N1 | 8.6 (2) | C8—N2—C14—O3 | −16.2 (2) |
C8—N2—C7—N1 | −173.70 (14) | C14—O3—C15—C17 | −61.3 (2) |
C14—N2—C8—C9 | 103.85 (18) | C14—O3—C15—C18 | 63.1 (2) |
C7—N2—C8—C9 | −74.0 (2) | C14—O3—C15—C16 | −179.11 (16) |
C14—N2—C8—C13 | −73.60 (19) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Se1 | 0.81 (2) | 2.69 (2) | 3.1417 (14) | 116.8 (18) |
N1—H1···Se2 | 0.81 (2) | 3.09 (2) | 3.5417 (15) | 117.9 (18) |
N1—H1···O2 | 0.81 (2) | 1.96 (2) | 2.6454 (19) | 142 (2) |
C5—H5···O1 | 0.91 (2) | 2.36 (2) | 2.888 (2) | 116.8 (17) |
C10—H10···Se1i | 0.92 (2) | 3.02 (2) | 3.4886 (18) | 112.9 (15) |
C13—H13···O2ii | 0.94 (2) | 2.65 (2) | 3.569 (2) | 166.0 (17) |
C17—H17B···O2 | 0.99 (3) | 2.46 (2) | 3.018 (3) | 115.1 (17) |
C18—H18B···O2 | 0.98 (3) | 2.47 (3) | 2.982 (3) | 112.2 (18) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1. |
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