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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[28.4.0.04,9.013,18.021,26]tetra­triaconta-1(30),4(9),5,7,13,15,17,21,23,25,31,33-dodeca­ene-10,27-di­carboxyl­ate, C36H34N4O6Se4, and its precursor di-tert-butyl 2,2′-[diselane-1,2-diylbis(2,1-phenyl­ene)]dicarbamate, C22H28N2O4Se2, 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\overline{1} with one mol­ecule in the unit cell (Z′ = 1 \over 2). 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619002341/fn3298sup1.cif
Contains datablocks 3, 4, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619002341/fn32983sup2.hkl
Contains datablock 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619002341/fn32984sup3.hkl
Contains datablock 4

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619002341/fn32983sup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619002341/fn32984sup5.cml
Supplementary material

CCDC references: 1897283; 1897282

Computing details top

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
C22H28N2O4Se2F(000) = 2192
Mr = 542.38Dx = 1.489 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 18.1780 (7) ÅCell parameters from 9904 reflections
b = 9.3386 (5) Åθ = 2.5–29.7°
c = 28.9009 (18) ŵ = 3.08 mm1
β = 99.440 (5)°T = 100 K
V = 4839.7 (4) Å3Prism, colourless
Z = 80.16 × 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 tubeRint = 0.079
ω scansθmax = 27.9°, θmin = 2.5°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)'
h = 2323
Tmin = 0.754, Tmax = 1.000k = 1212
37302 measured reflectionsl = 3836
5769 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.054H 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 reflectionsΔρmax = 0.85 e Å3
285 parametersΔρmin = 0.67 e Å3
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
xyzUiso*/Ueq
Se10.86339 (2)0.28216 (4)0.49219 (2)0.02931 (11)
Se20.86311 (2)0.52389 (4)0.51358 (2)0.03443 (12)
N10.74970 (17)0.2863 (4)0.39781 (13)0.0306 (7)
H1N0.746 (2)0.290 (4)0.4251 (15)0.031 (12)*
O20.68533 (16)0.2820 (4)0.32374 (11)0.0510 (9)
O30.62763 (14)0.2820 (4)0.38685 (10)0.0410 (7)
N20.74455 (19)0.6127 (4)0.42843 (12)0.0293 (7)
H2N0.787 (2)0.592 (5)0.4328 (15)0.035 (13)*
O50.65091 (15)0.7150 (4)0.37732 (11)0.0467 (8)
O60.76644 (14)0.6826 (3)0.36002 (9)0.0346 (7)
C10.8811 (2)0.2945 (4)0.42882 (14)0.0276 (8)
C20.9546 (2)0.2980 (5)0.42168 (16)0.0380 (10)
H2A0.9934260.3005760.4480640.046*
C30.9728 (2)0.2978 (5)0.37751 (17)0.0451 (11)
H3A1.0234130.2994980.3731230.054*
C40.9161 (2)0.2950 (5)0.33972 (17)0.0466 (11)
H4A0.9281250.2951930.3089440.056*
C50.8425 (2)0.2918 (5)0.34533 (15)0.0381 (10)
H5A0.8043480.2898420.3185960.046*
C60.8238 (2)0.2915 (4)0.39029 (14)0.0293 (8)
C70.6869 (2)0.2829 (4)0.36527 (15)0.0309 (9)
C80.5517 (2)0.2720 (5)0.35906 (14)0.0372 (10)
C90.5444 (3)0.1363 (6)0.3312 (2)0.0604 (15)
H9A0.5618610.0557070.3518340.091*
H9B0.5744850.1430150.3061370.091*
H9C0.4919610.1213700.3175120.091*
C100.5039 (2)0.2680 (8)0.39657 (18)0.075 (2)
H10A0.5159670.1824330.4159660.113*
H10B0.4512790.2652430.3821030.113*
H10C0.5132940.3537160.4162210.113*
C110.5361 (3)0.4024 (6)0.3290 (2)0.0595 (15)
H11A0.5493110.4881650.3480960.089*
H11B0.4829520.4054130.3156380.089*
H11C0.5657530.3989610.3036260.089*
C120.7578 (2)0.5542 (4)0.51048 (14)0.0302 (9)
C130.7281 (3)0.5382 (4)0.55114 (14)0.0360 (10)
H13A0.7599770.5137690.5794730.043*
C140.6534 (3)0.5570 (4)0.55131 (15)0.0383 (10)
H14A0.6334080.5459680.5794790.046*
C150.6077 (2)0.5921 (4)0.50989 (16)0.0382 (10)
H15A0.5557000.6040750.5095930.046*
C160.6364 (2)0.6102 (4)0.46876 (15)0.0323 (9)
H16A0.6041200.6343180.4405630.039*
C170.7124 (2)0.5931 (4)0.46861 (14)0.0290 (9)
C180.7138 (2)0.6745 (4)0.38731 (14)0.0295 (8)
C190.7477 (2)0.7340 (5)0.31132 (14)0.0355 (10)
C200.8205 (3)0.7129 (6)0.29334 (16)0.0550 (14)
H20A0.8351160.6118750.2965170.083*
H20B0.8592530.7721790.3116120.083*
H20C0.8142500.7407550.2602420.083*
C210.7267 (3)0.8899 (5)0.31093 (19)0.0631 (15)
H21A0.7658750.9438410.3309040.095*
H21B0.6795150.9006990.3228640.095*
H21C0.7208570.9265990.2787740.095*
C220.6876 (3)0.6411 (6)0.28424 (16)0.0532 (13)
H22A0.7004120.5400070.2899970.080*
H22B0.6833720.6615120.2506500.080*
H22C0.6398480.6613970.2945020.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se10.02644 (19)0.0251 (2)0.0347 (2)0.00019 (17)0.00028 (16)0.00124 (16)
Se20.0314 (2)0.0263 (2)0.0424 (3)0.00377 (18)0.00323 (17)0.00391 (18)
N10.0198 (15)0.042 (2)0.030 (2)0.0002 (15)0.0044 (14)0.0020 (16)
O20.0267 (15)0.094 (3)0.0324 (18)0.0036 (17)0.0032 (13)0.0010 (17)
O30.0173 (13)0.072 (2)0.0334 (16)0.0013 (14)0.0022 (11)0.0041 (15)
N20.0235 (17)0.0331 (19)0.0318 (19)0.0034 (15)0.0056 (15)0.0041 (14)
O50.0264 (15)0.070 (2)0.0454 (18)0.0156 (15)0.0113 (13)0.0166 (16)
O60.0245 (14)0.0505 (18)0.0299 (15)0.0035 (13)0.0078 (11)0.0058 (13)
C10.0234 (18)0.0197 (18)0.039 (2)0.0009 (16)0.0031 (16)0.0003 (16)
C20.0208 (19)0.038 (2)0.053 (3)0.0045 (18)0.0007 (18)0.002 (2)
C30.025 (2)0.053 (3)0.060 (3)0.000 (2)0.016 (2)0.007 (2)
C40.037 (2)0.062 (3)0.044 (3)0.002 (2)0.017 (2)0.003 (2)
C50.027 (2)0.050 (3)0.038 (2)0.002 (2)0.0073 (18)0.006 (2)
C60.0214 (18)0.028 (2)0.039 (2)0.0008 (16)0.0058 (16)0.0028 (17)
C70.0217 (18)0.034 (2)0.037 (2)0.0027 (17)0.0057 (16)0.0009 (18)
C80.0176 (18)0.059 (3)0.034 (2)0.0003 (19)0.0001 (16)0.000 (2)
C90.030 (2)0.058 (3)0.089 (4)0.009 (2)0.001 (3)0.014 (3)
C100.018 (2)0.165 (7)0.043 (3)0.002 (3)0.004 (2)0.002 (3)
C110.030 (2)0.057 (3)0.088 (4)0.005 (2)0.002 (3)0.015 (3)
C120.037 (2)0.0147 (18)0.038 (2)0.0009 (16)0.0048 (18)0.0043 (16)
C130.053 (3)0.023 (2)0.032 (2)0.000 (2)0.006 (2)0.0033 (16)
C140.058 (3)0.0196 (19)0.042 (3)0.0012 (19)0.022 (2)0.0016 (17)
C150.035 (2)0.028 (2)0.056 (3)0.0005 (18)0.020 (2)0.0040 (19)
C160.032 (2)0.0209 (19)0.045 (2)0.0003 (17)0.0120 (19)0.0010 (17)
C170.034 (2)0.0165 (17)0.037 (2)0.0007 (16)0.0092 (18)0.0017 (15)
C180.029 (2)0.030 (2)0.031 (2)0.0005 (17)0.0089 (17)0.0016 (16)
C190.030 (2)0.050 (3)0.027 (2)0.0024 (19)0.0038 (17)0.0101 (19)
C200.039 (3)0.092 (4)0.036 (3)0.004 (3)0.012 (2)0.008 (3)
C210.082 (4)0.051 (3)0.062 (3)0.013 (3)0.028 (3)0.021 (3)
C220.043 (3)0.079 (4)0.035 (3)0.012 (3)0.001 (2)0.007 (3)
Geometric parameters (Å, º) top
Se1—C11.914 (4)C9—H9C0.9800
Se1—Se22.3408 (6)C10—H10A0.9800
Se2—C121.923 (4)C10—H10B0.9800
N1—C71.356 (5)C10—H10C0.9800
N1—C61.399 (5)C11—H11A0.9800
N1—H1N0.80 (4)C11—H11B0.9800
O2—C71.196 (5)C11—H11C0.9800
O3—C71.330 (5)C12—C131.379 (6)
O3—C81.482 (4)C12—C171.396 (6)
N2—C181.356 (5)C13—C141.370 (6)
N2—C171.395 (5)C13—H13A0.9500
N2—H2N0.79 (4)C14—C151.380 (6)
O5—C181.194 (5)C14—H14A0.9500
O6—C181.338 (4)C15—C161.385 (6)
O6—C191.473 (5)C15—H15A0.9500
C1—C21.386 (5)C16—C171.392 (5)
C1—C61.395 (5)C16—H16A0.9500
C2—C31.370 (6)C19—C211.504 (6)
C2—H2A0.9500C19—C221.511 (6)
C3—C41.373 (6)C19—C201.511 (6)
C3—H3A0.9500C20—H20A0.9800
C4—C51.375 (6)C20—H20B0.9800
C4—H4A0.9500C20—H20C0.9800
C5—C61.396 (6)C21—H21A0.9800
C5—H5A0.9500C21—H21B0.9800
C8—C91.495 (7)C21—H21C0.9800
C8—C111.495 (6)C22—H22A0.9800
C8—C101.496 (6)C22—H22B0.9800
C9—H9A0.9800C22—H22C0.9800
C9—H9B0.9800
C1—Se1—Se2101.68 (11)C8—C11—H11B109.5
C12—Se2—Se1100.07 (11)H11A—C11—H11B109.5
C7—N1—C6128.0 (4)C8—C11—H11C109.5
C7—N1—H1N120 (3)H11A—C11—H11C109.5
C6—N1—H1N112 (3)H11B—C11—H11C109.5
C7—O3—C8120.0 (3)C13—C12—C17120.6 (4)
C18—N2—C17128.1 (3)C13—C12—Se2118.0 (3)
C18—N2—H2N120 (3)C17—C12—Se2121.4 (3)
C17—N2—H2N112 (3)C14—C13—C12121.0 (4)
C18—O6—C19120.4 (3)C14—C13—H13A119.5
C2—C1—C6119.6 (4)C12—C13—H13A119.5
C2—C1—Se1117.5 (3)C13—C14—C15118.9 (4)
C6—C1—Se1122.8 (3)C13—C14—H14A120.5
C3—C2—C1121.6 (4)C15—C14—H14A120.5
C3—C2—H2A119.2C14—C15—C16121.0 (4)
C1—C2—H2A119.2C14—C15—H15A119.5
C2—C3—C4118.6 (4)C16—C15—H15A119.5
C2—C3—H3A120.7C15—C16—C17120.2 (4)
C4—C3—H3A120.7C15—C16—H16A119.9
C3—C4—C5121.6 (4)C17—C16—H16A119.9
C3—C4—H4A119.2C16—C17—N2122.6 (4)
C5—C4—H4A119.2C16—C17—C12118.2 (4)
C4—C5—C6120.0 (4)N2—C17—C12119.2 (4)
C4—C5—H5A120.0O5—C18—O6126.1 (4)
C6—C5—H5A120.0O5—C18—N2125.9 (4)
C1—C6—C5118.6 (3)O6—C18—N2108.0 (3)
C1—C6—N1119.3 (4)O6—C19—C21110.0 (4)
C5—C6—N1122.2 (4)O6—C19—C22110.0 (3)
O2—C7—O3125.7 (4)C21—C19—C22113.0 (4)
O2—C7—N1125.1 (4)O6—C19—C20102.0 (3)
O3—C7—N1109.2 (3)C21—C19—C20111.1 (4)
O3—C8—C9109.7 (4)C22—C19—C20110.3 (4)
O3—C8—C11109.5 (4)C19—C20—H20A109.5
C9—C8—C11112.7 (4)C19—C20—H20B109.5
O3—C8—C10102.0 (3)H20A—C20—H20B109.5
C9—C8—C10111.0 (5)C19—C20—H20C109.5
C11—C8—C10111.4 (4)H20A—C20—H20C109.5
C8—C9—H9A109.5H20B—C20—H20C109.5
C8—C9—H9B109.5C19—C21—H21A109.5
H9A—C9—H9B109.5C19—C21—H21B109.5
C8—C9—H9C109.5H21A—C21—H21B109.5
H9A—C9—H9C109.5C19—C21—H21C109.5
H9B—C9—H9C109.5H21A—C21—H21C109.5
C8—C10—H10A109.5H21B—C21—H21C109.5
C8—C10—H10B109.5C19—C22—H22A109.5
H10A—C10—H10B109.5C19—C22—H22B109.5
C8—C10—H10C109.5H22A—C22—H22B109.5
H10A—C10—H10C109.5C19—C22—H22C109.5
H10B—C10—H10C109.5H22A—C22—H22C109.5
C8—C11—H11A109.5H22B—C22—H22C109.5
C6—C1—C2—C30.3 (6)C17—C12—C13—C141.4 (6)
Se1—C1—C2—C3175.9 (3)Se2—C12—C13—C14179.4 (3)
C1—C2—C3—C40.4 (7)C12—C13—C14—C150.2 (6)
C2—C3—C4—C50.3 (8)C13—C14—C15—C160.8 (6)
C3—C4—C5—C60.0 (7)C14—C15—C16—C170.0 (6)
C2—C1—C6—C50.1 (6)C15—C16—C17—N2178.7 (4)
Se1—C1—C6—C5175.9 (3)C15—C16—C17—C121.5 (5)
C2—C1—C6—N1179.3 (4)C18—N2—C17—C1613.4 (6)
Se1—C1—C6—N13.3 (5)C18—N2—C17—C12166.9 (4)
C4—C5—C6—C10.1 (6)C13—C12—C17—C162.2 (5)
C4—C5—C6—N1179.1 (4)Se2—C12—C17—C16178.6 (3)
C7—N1—C6—C1179.9 (4)C13—C12—C17—N2178.0 (3)
C7—N1—C6—C50.9 (7)Se2—C12—C17—N21.2 (5)
C8—O3—C7—O23.3 (7)C19—O6—C18—O55.4 (6)
C8—O3—C7—N1177.3 (4)C19—O6—C18—N2174.8 (3)
C6—N1—C7—O20.9 (7)C17—N2—C18—O55.4 (7)
C6—N1—C7—O3178.5 (4)C17—N2—C18—O6174.4 (4)
C7—O3—C8—C959.9 (5)C18—O6—C19—C2166.8 (5)
C7—O3—C8—C1164.3 (5)C18—O6—C19—C2258.3 (5)
C7—O3—C8—C10177.6 (4)C18—O6—C19—C20175.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···Se10.80 (4)2.63 (4)3.141 (3)123 (4)
N2—H2N···Se20.79 (4)2.59 (4)3.106 (3)125 (4)
C2—H2A···Se2i0.953.133.900 (4)140
C5—H5A···O20.952.192.824 (5)123
C9—H9B···O20.982.382.941 (6)116
C10—H10A···Se1ii0.983.173.719 (5)117
C11—H11C···O20.982.422.964 (6)115
C16—H16A···O50.952.272.871 (5)121
C20—H20C···O2iii0.982.463.429 (6)171
C21—H21B···O50.982.453.019 (6)116
C22—H22A···O20.982.633.544 (7)155
C22—H22C···O50.982.422.957 (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[28.4.0.04,9.013,18.021,26]tetratriaconta-1(30),4(9),5,7,13,15,17,21,23,25,31,33-dodecaene-10,27-dicarboxylate (4) top
Crystal data top
C36H34N4O6Se4Z = 1
Mr = 934.51F(000) = 462
Triclinic, P1Dx = 1.704 Mg m3
a = 9.4865 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.7410 (2) ÅCell parameters from 15479 reflections
c = 11.2789 (3) Åθ = 2.4–31.3°
α = 101.000 (2)°µ = 4.08 mm1
β = 108.394 (2)°T = 100 K
γ = 105.264 (2)°Needle, clear intense orange
V = 910.42 (4) Å30.17 × 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 tubeRint = 0.037
ω scansθmax = 31.2°, θmin = 2.4°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
h = 1313
Tmin = 0.823, Tmax = 1.000k = 1414
23930 measured reflectionsl = 1615
5406 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026All 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 reflectionsΔρmax = 0.69 e Å3
294 parametersΔρmin = 0.47 e Å3
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
xyzUiso*/Ueq
Se10.04380 (2)0.49656 (2)0.30624 (2)0.02120 (5)
Se20.20175 (2)0.43386 (2)0.47712 (2)0.02078 (5)
O10.62718 (14)0.68582 (15)0.30763 (12)0.0268 (3)
O20.39283 (14)0.78120 (14)0.54761 (12)0.0245 (3)
O30.63606 (14)0.85044 (14)0.70736 (11)0.0236 (2)
N10.38224 (16)0.65545 (16)0.31384 (14)0.0212 (3)
H10.341 (3)0.677 (2)0.364 (2)0.028 (6)*
N20.61486 (15)0.79034 (15)0.50056 (13)0.0188 (3)
C10.13119 (19)0.46199 (18)0.17561 (16)0.0206 (3)
C20.0308 (2)0.3550 (2)0.05685 (18)0.0254 (3)
H20.070 (2)0.298 (2)0.052 (2)0.025 (5)*
C30.0783 (2)0.3337 (2)0.04709 (18)0.0292 (4)
H30.006 (3)0.266 (3)0.126 (2)0.038 (6)*
C40.2278 (2)0.4198 (2)0.03280 (18)0.0289 (4)
H40.257 (3)0.413 (2)0.099 (2)0.029 (6)*
C50.3309 (2)0.5270 (2)0.08602 (18)0.0254 (3)
H50.427 (3)0.587 (2)0.095 (2)0.030 (6)*
C60.28439 (19)0.54868 (18)0.19161 (16)0.0200 (3)
C70.54289 (18)0.70675 (18)0.36558 (16)0.0192 (3)
C80.78540 (18)0.86088 (18)0.55745 (15)0.0191 (3)
C90.88618 (18)0.78022 (18)0.58540 (16)0.0190 (3)
C101.0487 (2)0.8571 (2)0.65130 (18)0.0246 (3)
H101.115 (2)0.803 (2)0.668 (2)0.023 (5)*
C111.1079 (2)1.0112 (2)0.68627 (18)0.0259 (4)
H111.216 (3)1.063 (3)0.728 (2)0.040 (6)*
C121.0078 (2)1.0906 (2)0.65271 (17)0.0241 (3)
H121.048 (2)1.191 (2)0.666 (2)0.025 (5)*
C130.8458 (2)1.01533 (19)0.58854 (17)0.0221 (3)
H130.776 (2)1.067 (2)0.564 (2)0.021 (5)*
C140.53423 (19)0.80575 (18)0.58434 (16)0.0193 (3)
C150.5869 (2)0.8912 (2)0.81793 (17)0.0239 (3)
C160.7421 (3)0.9359 (3)0.9349 (2)0.0343 (4)
H16A0.734 (3)0.967 (3)1.013 (3)0.043 (7)*
H16C0.813 (3)1.004 (3)0.926 (2)0.042 (7)*
C170.5305 (3)1.0216 (3)0.8070 (2)0.0378 (5)
H17A0.608 (3)1.099 (3)0.801 (2)0.033 (6)*
H17B0.436 (3)0.997 (3)0.726 (3)0.039 (6)*
H17C0.514 (4)1.044 (3)0.883 (3)0.063 (9)*
C180.4628 (3)0.7560 (3)0.8179 (2)0.0353 (4)
H18A0.447 (3)0.781 (3)0.896 (3)0.055 (8)*
H18B0.361 (3)0.723 (3)0.744 (3)0.044 (7)*
H18C0.501 (3)0.673 (3)0.814 (3)0.054 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se10.01818 (8)0.02274 (9)0.02408 (9)0.00897 (6)0.00741 (6)0.00874 (7)
Se20.02023 (8)0.01904 (9)0.02065 (9)0.00580 (6)0.00545 (6)0.00628 (6)
O10.0208 (6)0.0346 (7)0.0212 (6)0.0060 (5)0.0097 (5)0.0026 (5)
O20.0186 (5)0.0307 (7)0.0229 (6)0.0104 (5)0.0076 (5)0.0039 (5)
O30.0214 (5)0.0324 (7)0.0178 (6)0.0116 (5)0.0076 (5)0.0058 (5)
N10.0178 (6)0.0256 (7)0.0176 (6)0.0061 (5)0.0062 (5)0.0035 (6)
N20.0157 (6)0.0206 (6)0.0178 (6)0.0051 (5)0.0059 (5)0.0038 (5)
C10.0204 (7)0.0211 (7)0.0200 (7)0.0084 (6)0.0053 (6)0.0076 (6)
C20.0226 (8)0.0225 (8)0.0253 (9)0.0078 (7)0.0032 (7)0.0050 (7)
C30.0326 (9)0.0256 (9)0.0202 (8)0.0109 (7)0.0018 (7)0.0002 (7)
C40.0336 (9)0.0355 (10)0.0186 (8)0.0166 (8)0.0085 (7)0.0064 (7)
C50.0238 (8)0.0317 (9)0.0211 (8)0.0114 (7)0.0075 (7)0.0084 (7)
C60.0201 (7)0.0209 (7)0.0174 (7)0.0080 (6)0.0038 (6)0.0063 (6)
C70.0190 (7)0.0188 (7)0.0187 (7)0.0055 (6)0.0056 (6)0.0070 (6)
C80.0162 (7)0.0210 (8)0.0167 (7)0.0035 (6)0.0053 (6)0.0044 (6)
C90.0183 (7)0.0186 (7)0.0192 (7)0.0044 (6)0.0071 (6)0.0063 (6)
C100.0190 (7)0.0282 (9)0.0258 (9)0.0077 (7)0.0068 (7)0.0101 (7)
C110.0185 (7)0.0280 (9)0.0237 (8)0.0003 (7)0.0055 (7)0.0069 (7)
C120.0258 (8)0.0209 (8)0.0206 (8)0.0019 (7)0.0093 (7)0.0033 (7)
C130.0240 (8)0.0220 (8)0.0211 (8)0.0087 (6)0.0098 (6)0.0056 (7)
C140.0203 (7)0.0187 (7)0.0193 (7)0.0082 (6)0.0076 (6)0.0048 (6)
C150.0291 (8)0.0270 (8)0.0188 (8)0.0117 (7)0.0120 (7)0.0060 (7)
C160.0335 (10)0.0429 (12)0.0188 (9)0.0087 (9)0.0062 (8)0.0053 (8)
C170.0512 (13)0.0359 (11)0.0330 (11)0.0271 (11)0.0165 (10)0.0078 (9)
C180.0383 (11)0.0388 (11)0.0299 (10)0.0085 (9)0.0178 (9)0.0118 (9)
Geometric parameters (Å, º) top
Se1—C11.9235 (17)C5—H50.91 (2)
Se1—Se22.3327 (2)C8—C91.389 (2)
Se2—C9i1.9219 (16)C8—C131.390 (2)
O1—C71.214 (2)C9—C101.395 (2)
O2—C141.2128 (19)C10—C111.384 (3)
O3—C141.323 (2)C10—H100.92 (2)
O3—C151.486 (2)C11—C121.384 (3)
N1—C71.356 (2)C11—H110.93 (2)
N1—C61.407 (2)C12—C131.388 (2)
N1—H10.81 (2)C12—H120.92 (2)
N2—C141.401 (2)C13—H130.94 (2)
N2—C71.423 (2)C15—C171.513 (3)
N2—C81.4465 (19)C15—C181.518 (3)
C1—C21.388 (2)C15—C161.522 (3)
C1—C61.410 (2)C16—H16A0.91 (3)
C2—C31.382 (3)C16—H16C0.85 (3)
C2—H20.95 (2)C17—H17A0.93 (2)
C3—C41.385 (3)C17—H17B0.99 (3)
C3—H30.92 (2)C17—H17C0.92 (3)
C4—C51.394 (3)C18—H18A0.94 (3)
C4—H40.87 (2)C18—H18B0.98 (3)
C5—C61.394 (2)C18—H18C0.96 (3)
C1—Se1—Se2102.63 (5)C11—C10—C9120.19 (16)
C9i—Se2—Se1101.30 (5)C11—C10—H10121.4 (13)
C14—O3—C15121.28 (13)C9—C10—H10118.4 (13)
C7—N1—C6125.87 (15)C12—C11—C10120.59 (16)
C7—N1—H1115.5 (16)C12—C11—H11118.4 (15)
C6—N1—H1117.5 (16)C10—C11—H11120.9 (15)
C14—N2—C7125.19 (13)C11—C12—C13119.62 (17)
C14—N2—C8117.10 (13)C11—C12—H12120.8 (13)
C7—N2—C8117.67 (13)C13—C12—H12119.4 (13)
C2—C1—C6119.88 (16)C12—C13—C8119.86 (16)
C2—C1—Se1116.87 (13)C12—C13—H13121.2 (12)
C6—C1—Se1122.99 (12)C8—C13—H13118.9 (12)
C3—C2—C1120.76 (17)O2—C14—O3126.26 (15)
C3—C2—H2122.7 (13)O2—C14—N2124.34 (15)
C1—C2—H2116.5 (13)O3—C14—N2109.40 (13)
C2—C3—C4119.73 (17)O3—C15—C17108.43 (15)
C2—C3—H3118.1 (15)O3—C15—C18109.81 (15)
C4—C3—H3122.0 (15)C17—C15—C18113.42 (18)
C3—C4—C5120.40 (18)O3—C15—C16101.27 (14)
C3—C4—H4120.8 (15)C17—C15—C16111.86 (17)
C5—C4—H4118.6 (15)C18—C15—C16111.31 (17)
C6—C5—C4120.28 (17)C15—C16—H16A113.0 (16)
C6—C5—H5118.9 (14)C15—C16—H16C108.9 (17)
C4—C5—H5120.8 (14)H16A—C16—H16C110 (2)
C5—C6—N1123.14 (15)C15—C17—H17A110.0 (14)
C5—C6—C1118.94 (16)C15—C17—H17B112.9 (14)
N1—C6—C1117.91 (15)H17A—C17—H17B105 (2)
O1—C7—N1125.85 (16)C15—C17—H17C101.4 (19)
O1—C7—N2118.81 (14)H17A—C17—H17C113 (2)
N1—C7—N2115.33 (14)H17B—C17—H17C115 (2)
C9—C8—C13120.65 (15)C15—C18—H18A107.7 (17)
C9—C8—N2122.21 (14)C15—C18—H18B113.9 (15)
C13—C8—N2117.10 (14)H18A—C18—H18B109 (2)
C8—C9—C10118.97 (15)C15—C18—H18C109.5 (17)
C8—C9—Se2i118.80 (12)H18A—C18—H18C110 (2)
C10—C9—Se2i122.12 (13)H18B—C18—H18C107 (2)
C6—C1—C2—C31.0 (3)C7—N2—C8—C13108.54 (17)
Se1—C1—C2—C3173.31 (14)C13—C8—C9—C103.3 (2)
C1—C2—C3—C40.0 (3)N2—C8—C9—C10174.09 (15)
C2—C3—C4—C50.5 (3)C13—C8—C9—Se2i173.12 (12)
C3—C4—C5—C60.1 (3)N2—C8—C9—Se2i9.5 (2)
C4—C5—C6—N1179.62 (16)C8—C9—C10—C110.9 (3)
C4—C5—C6—C10.8 (3)Se2i—C9—C10—C11175.31 (14)
C7—N1—C6—C528.0 (3)C9—C10—C11—C122.1 (3)
C7—N1—C6—C1153.19 (16)C10—C11—C12—C132.9 (3)
C2—C1—C6—C51.3 (2)C11—C12—C13—C80.6 (3)
Se1—C1—C6—C5172.56 (13)C9—C8—C13—C122.5 (3)
C2—C1—C6—N1179.79 (15)N2—C8—C13—C12174.96 (15)
Se1—C1—C6—N16.3 (2)C15—O3—C14—O26.4 (3)
C6—N1—C7—O111.6 (3)C15—O3—C14—N2173.61 (13)
C6—N1—C7—N2167.49 (15)C7—N2—C14—O218.5 (3)
C14—N2—C7—O1170.50 (15)C8—N2—C14—O2163.79 (16)
C8—N2—C7—O17.2 (2)C7—N2—C14—O3161.44 (14)
C14—N2—C7—N18.6 (2)C8—N2—C14—O316.2 (2)
C8—N2—C7—N1173.70 (14)C14—O3—C15—C1761.3 (2)
C14—N2—C8—C9103.85 (18)C14—O3—C15—C1863.1 (2)
C7—N2—C8—C974.0 (2)C14—O3—C15—C16179.11 (16)
C14—N2—C8—C1373.60 (19)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Se10.81 (2)2.69 (2)3.1417 (14)116.8 (18)
N1—H1···Se20.81 (2)3.09 (2)3.5417 (15)117.9 (18)
N1—H1···O20.81 (2)1.96 (2)2.6454 (19)142 (2)
C5—H5···O10.91 (2)2.36 (2)2.888 (2)116.8 (17)
C10—H10···Se1i0.92 (2)3.02 (2)3.4886 (18)112.9 (15)
C13—H13···O2ii0.94 (2)2.65 (2)3.569 (2)166.0 (17)
C17—H17B···O20.99 (3)2.46 (2)3.018 (3)115.1 (17)
C18—H18B···O20.98 (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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