Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619002341/fn3298sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619002341/fn32983sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619002341/fn32984sup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619002341/fn32983sup4.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619002341/fn32984sup5.cml |
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).
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 |
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 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 |
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. |
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* |
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) |
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) |
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. |
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 |
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 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 |
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. |
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)* |
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) |
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. |
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. |