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Seven novel lanthanide coordination polymers, [Eu(STP)(glu)]n (1), [Ln4(STP)2(glu)5]n·4nH2O [Ln = Er (2), Yb (3)], [Ln(STP)(1,3-bdc)]n·0.5nH2O [Ln = Tb (4), Yb (5)], and [Ln(STP)(1,2-bdc)]n [Ln = Eu (6), Tb (7)] [NaSTP = sodium 2-(2,2′:6′,2″-terpyridin-4′-yl)benzene­sulfonate, H2glu = glutaric acid, H2(1,3-bdc) = benzene-1,3-di­carb­oxy­lic acid, H2(1,2-bdc) = benzene-1,2-di­carb­oxy­lic acid], have been prepared under hydro­thermal conditions and characterized by elemental analysis, IR and single-crystal X-ray diffraction. Compound (1) possesses a 2D layered structure based on 1D chains with STP and glu2− anions acting as bridges. Compounds (2) and (3) are isomorphous and show a rare 3D tcj/hc net with a tetranuclear Ln3+ unit regarded as a seven-connected node and a glu2− anion serving as a three-connected node. Compounds (4) and (5) are isomorphous and exhibit six-connected pcu nets by denoting binuclear units to six-connected nodes. Compounds (6) and (7) display 3D 3,5T1 nets with (1,2-bdc)2− anions and dimetallic units serving as three- and five-connected nodes, respectively. The Eu compounds (1) and (6) demonstrate typically red emission, while the Tb compounds (4) and (7) exhibit characteristic green emission. The emission spectra of heteronuclear compounds [EuxTb1−x(STP)(1,2-bdc)]n (0 ≤ x ≤ 1) as efficient luminescent tags were investigated. The intermetallic energy transfer of Tb to Eu was also evaluated.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520619010047/um5030sup1.cif
Contains datablocks global, 1, 2, 3, 4, 5, 6, 7

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520619010047/um5030sup2.pdf
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520619010047/um50301sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520619010047/um50302sup3.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520619010047/um50303sup4.hkl
Contains datablock 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520619010047/um50304sup5.hkl
Contains datablock 4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520619010047/um50305sup6.hkl
Contains datablock 5

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520619010047/um50306sup7.hkl
Contains datablock 6

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520619010047/um50307sup8.hkl
Contains datablock 7

CCDC references: 1536340; 1536341; 1536342; 1536343; 1536344; 1536345; 1536346

Computing details top

For all structures, data collection: Bruker APEX2; cell refinement: Bruker SAINT; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014); molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.

(1) top
Crystal data top
C26H20EuN3O7SF(000) = 1328
Mr = 670.47Dx = 1.693 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.9849 (12) ÅCell parameters from 5562 reflections
b = 13.1957 (11) Åθ = 2.3–26.3°
c = 15.1425 (13) ŵ = 2.51 mm1
β = 109.763 (1)°T = 296 K
V = 2629.8 (4) Å3Block, yellow
Z = 40.18 × 0.16 × 0.12 mm
Data collection top
Bruker APEX-II CCD
diffractometer
3915 reflections with I > 2σ(I)
φ and ω scansRint = 0.029
Absorption correction: multi-scan
sadabs
θmax = 25.1°, θmin = 2.2°
Tmin = 0.64, Tmax = 0.742h = 1611
13035 measured reflectionsk = 1315
4645 independent reflectionsl = 1816
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024H-atom parameters constrained
wR(F2) = 0.057 w = 1/[σ2(Fo2) + (0.0227P)2 + 2.2328P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.003
4645 reflectionsΔρmax = 0.97 e Å3
343 parametersΔρmin = 0.42 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
Eu10.63574 (2)0.42545 (2)0.53001 (2)0.01543 (6)
S10.88491 (7)0.17050 (7)0.19280 (7)0.0269 (2)
N10.7823 (2)0.5522 (2)0.5446 (2)0.0225 (7)
N20.7476 (2)0.3936 (2)0.42842 (19)0.0202 (7)
N30.6518 (2)0.2374 (2)0.4749 (2)0.0260 (7)
O10.77829 (18)0.13743 (18)0.15226 (17)0.0268 (6)
O20.9505 (2)0.1164 (2)0.1531 (2)0.0439 (8)
O30.9179 (2)0.1711 (2)0.29345 (18)0.0372 (7)
O40.5618 (2)0.31558 (18)0.61858 (17)0.0285 (6)
O50.4442 (2)0.42007 (18)0.53665 (17)0.0300 (6)
O60.36890 (18)0.03009 (18)0.84260 (16)0.0228 (5)
O70.5175 (2)0.1113 (2)0.87794 (18)0.0397 (7)
C10.8076 (3)0.6227 (3)0.6111 (3)0.0364 (10)
H10.77300.62360.65390.044*
C20.8818 (3)0.6948 (3)0.6206 (3)0.0431 (11)
H20.89630.74330.66790.052*
C30.9334 (4)0.6929 (3)0.5587 (3)0.0453 (12)
H30.98390.74030.56300.054*
C40.9098 (3)0.6199 (3)0.4897 (3)0.0398 (11)
H40.94410.61770.44670.048*
C50.8343 (3)0.5497 (3)0.4849 (2)0.0210 (8)
C60.8088 (3)0.4668 (3)0.4147 (2)0.0210 (8)
C70.8480 (3)0.4623 (3)0.3425 (3)0.0289 (9)
H70.89370.51150.33770.035*
C80.8191 (3)0.3839 (3)0.2764 (3)0.0276 (9)
C90.7560 (3)0.3102 (3)0.2910 (2)0.0262 (9)
H90.73310.25800.24780.031*
C100.7267 (3)0.3135 (3)0.3695 (2)0.0215 (8)
C110.6783 (3)0.2250 (3)0.3980 (2)0.0226 (8)
C120.6703 (3)0.1329 (3)0.3528 (3)0.0392 (11)
H120.68920.12650.29980.047*
C130.6341 (5)0.0507 (3)0.3874 (4)0.0611 (16)
H130.62610.01150.35690.073*
C140.6102 (5)0.0614 (3)0.4668 (4)0.0604 (15)
H140.58850.00580.49270.072*
C150.6181 (4)0.1553 (3)0.5086 (3)0.0419 (11)
H150.59960.16230.56180.050*
C160.8546 (3)0.3852 (3)0.1943 (3)0.0315 (9)
C170.8608 (4)0.4786 (3)0.1549 (3)0.0480 (13)
H170.84570.53660.18250.058*
C180.8889 (4)0.4890 (4)0.0754 (3)0.0598 (15)
H180.89200.55290.05070.072*
C190.9117 (4)0.4052 (4)0.0340 (3)0.0547 (14)
H190.92850.41120.02020.066*
C200.9096 (3)0.3113 (3)0.0734 (3)0.0409 (11)
H200.92680.25440.04570.049*
C210.8827 (3)0.2991 (3)0.1527 (3)0.0293 (9)
C220.4740 (3)0.3506 (3)0.5981 (2)0.0225 (8)
C230.4030 (3)0.3105 (3)0.6448 (3)0.0382 (11)
H23A0.33980.29090.59680.046*
H23B0.38760.36440.68150.046*
C240.4437 (3)0.2212 (3)0.7078 (3)0.0333 (10)
H24A0.50850.24010.75380.040*
H24B0.45640.16660.67040.040*
C250.3759 (3)0.1816 (3)0.7593 (3)0.0317 (9)
H25A0.31470.15400.71380.038*
H25B0.35580.23790.79040.038*
C260.4249 (3)0.1003 (3)0.8319 (2)0.0234 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Eu10.01755 (10)0.01500 (9)0.01540 (9)0.00035 (8)0.00777 (7)0.00000 (7)
S10.0208 (5)0.0326 (5)0.0293 (5)0.0056 (4)0.0112 (4)0.0091 (4)
N10.0250 (17)0.0215 (17)0.0250 (16)0.0035 (13)0.0139 (14)0.0051 (12)
N20.0225 (16)0.0189 (15)0.0208 (15)0.0023 (13)0.0094 (13)0.0026 (12)
N30.0319 (18)0.0209 (16)0.0296 (17)0.0010 (14)0.0163 (15)0.0004 (13)
O10.0219 (14)0.0301 (14)0.0279 (14)0.0075 (12)0.0078 (12)0.0071 (11)
O20.0340 (17)0.0457 (17)0.062 (2)0.0014 (15)0.0293 (16)0.0103 (15)
O30.0351 (16)0.0432 (17)0.0282 (15)0.0079 (14)0.0040 (13)0.0083 (13)
O40.0288 (15)0.0266 (14)0.0359 (15)0.0049 (12)0.0184 (13)0.0102 (12)
O50.0332 (15)0.0243 (14)0.0272 (14)0.0045 (12)0.0034 (12)0.0117 (12)
O60.0239 (13)0.0237 (13)0.0213 (13)0.0053 (12)0.0082 (11)0.0029 (10)
O70.0278 (16)0.0509 (18)0.0326 (16)0.0123 (14)0.0001 (13)0.0229 (13)
C10.037 (2)0.046 (3)0.037 (2)0.013 (2)0.026 (2)0.017 (2)
C20.045 (3)0.044 (3)0.047 (3)0.019 (2)0.024 (2)0.023 (2)
C30.050 (3)0.045 (3)0.047 (3)0.028 (2)0.025 (2)0.017 (2)
C40.045 (3)0.047 (3)0.038 (2)0.023 (2)0.028 (2)0.016 (2)
C50.0203 (19)0.0192 (19)0.0242 (19)0.0032 (15)0.0086 (16)0.0037 (14)
C60.0206 (19)0.0227 (18)0.0212 (18)0.0019 (16)0.0088 (16)0.0029 (15)
C70.033 (2)0.026 (2)0.034 (2)0.0088 (18)0.0199 (19)0.0069 (17)
C80.033 (2)0.029 (2)0.027 (2)0.0013 (18)0.0179 (18)0.0038 (16)
C90.028 (2)0.027 (2)0.027 (2)0.0075 (17)0.0125 (17)0.0092 (16)
C100.0183 (18)0.0230 (19)0.0235 (19)0.0013 (16)0.0076 (16)0.0044 (15)
C110.024 (2)0.0212 (19)0.0224 (19)0.0003 (16)0.0081 (16)0.0018 (15)
C120.057 (3)0.026 (2)0.043 (3)0.011 (2)0.028 (2)0.0108 (19)
C130.104 (5)0.031 (3)0.068 (4)0.021 (3)0.054 (3)0.019 (2)
C140.097 (4)0.024 (3)0.080 (4)0.016 (3)0.057 (4)0.001 (2)
C150.064 (3)0.026 (2)0.050 (3)0.003 (2)0.038 (3)0.001 (2)
C160.038 (2)0.035 (2)0.029 (2)0.0086 (19)0.0201 (19)0.0066 (18)
C170.080 (4)0.030 (2)0.050 (3)0.015 (2)0.044 (3)0.007 (2)
C180.103 (5)0.039 (3)0.056 (3)0.017 (3)0.052 (3)0.003 (2)
C190.080 (4)0.056 (3)0.047 (3)0.018 (3)0.045 (3)0.005 (2)
C200.047 (3)0.048 (3)0.039 (2)0.012 (2)0.031 (2)0.015 (2)
C210.029 (2)0.034 (2)0.032 (2)0.0122 (18)0.0185 (18)0.0106 (17)
C220.028 (2)0.0195 (19)0.0191 (18)0.0038 (17)0.0076 (16)0.0018 (15)
C230.034 (2)0.044 (3)0.042 (2)0.008 (2)0.021 (2)0.024 (2)
C240.030 (2)0.036 (2)0.035 (2)0.0013 (19)0.0116 (19)0.0179 (18)
C250.029 (2)0.031 (2)0.037 (2)0.0028 (18)0.0144 (19)0.0160 (18)
C260.027 (2)0.026 (2)0.0174 (18)0.0004 (17)0.0073 (17)0.0040 (15)
Geometric parameters (Å, º) top
Eu1—O1i2.365 (2)C6—C71.380 (5)
Eu1—O5ii2.379 (2)C7—C81.401 (5)
Eu1—O7iii2.387 (3)C7—H70.9300
Eu1—O6iv2.391 (2)C8—C91.381 (5)
Eu1—O42.430 (2)C8—C161.486 (5)
Eu1—N22.572 (3)C9—C101.382 (5)
Eu1—N12.597 (3)C9—H90.9300
Eu1—N32.652 (3)C10—C111.485 (5)
Eu1—O52.715 (3)C11—C121.381 (5)
Eu1—Eu1ii4.0961 (4)C12—C131.373 (6)
S1—O31.435 (3)C12—H120.9300
S1—O21.444 (3)C13—C141.360 (6)
S1—O11.474 (3)C13—H130.9300
S1—C211.798 (4)C14—C151.379 (6)
N1—C11.329 (5)C14—H140.9300
N1—C51.338 (4)C15—H150.9300
N2—C101.351 (4)C16—C171.386 (6)
N2—C61.352 (4)C16—C211.417 (5)
N3—C111.346 (4)C17—C181.394 (6)
N3—C151.348 (5)C17—H170.9300
O1—Eu1iii2.365 (2)C18—C191.360 (6)
O4—C221.249 (4)C18—H180.9300
O5—C221.272 (4)C19—C201.380 (6)
O5—Eu1ii2.379 (2)C19—H190.9300
O6—C261.259 (4)C20—C211.385 (5)
O6—Eu1v2.391 (2)C20—H200.9300
O7—C261.255 (4)C22—C231.498 (5)
O7—Eu1i2.387 (3)C23—C241.501 (5)
C1—C21.379 (5)C23—H23A0.9700
C1—H10.9300C23—H23B0.9700
C2—C31.363 (6)C24—C251.510 (5)
C2—H20.9300C24—H24A0.9700
C3—C41.376 (5)C24—H24B0.9700
C3—H30.9300C25—C261.524 (5)
C4—C51.388 (5)C25—H25A0.9700
C4—H40.9300C25—H25B0.9700
C5—C61.483 (5)
O1i—Eu1—O5ii141.57 (9)C3—C4—H4120.4
O1i—Eu1—O7iii144.04 (9)C5—C4—H4120.4
O5ii—Eu1—O7iii72.06 (9)N1—C5—C4121.7 (3)
O1i—Eu1—O6iv79.44 (8)N1—C5—C6116.7 (3)
O5ii—Eu1—O6iv73.17 (8)C4—C5—C6121.6 (3)
O7iii—Eu1—O6iv134.17 (8)N2—C6—C7122.2 (3)
O1i—Eu1—O476.23 (9)N2—C6—C5115.3 (3)
O5ii—Eu1—O4121.24 (9)C7—C6—C5122.4 (3)
O7iii—Eu1—O497.24 (10)C6—C7—C8120.1 (3)
O6iv—Eu1—O476.51 (8)C6—C7—H7119.9
O1i—Eu1—N283.61 (9)C8—C7—H7119.9
O5ii—Eu1—N2100.35 (9)C9—C8—C7116.8 (3)
O7iii—Eu1—N275.68 (9)C9—C8—C16123.6 (3)
O6iv—Eu1—N2139.88 (9)C7—C8—C16119.5 (3)
O4—Eu1—N2133.69 (8)C8—C9—C10120.5 (3)
O1i—Eu1—N174.16 (9)C8—C9—H9119.8
O5ii—Eu1—N174.25 (9)C10—C9—H9119.8
O7iii—Eu1—N1118.83 (10)N2—C10—C9122.1 (3)
O6iv—Eu1—N178.20 (9)N2—C10—C11116.2 (3)
O4—Eu1—N1143.92 (9)C9—C10—C11121.5 (3)
N2—Eu1—N162.21 (9)N3—C11—C12122.4 (3)
O1i—Eu1—N377.25 (9)N3—C11—C10116.2 (3)
O5ii—Eu1—N3138.24 (9)C12—C11—C10121.1 (3)
O7iii—Eu1—N367.11 (9)C13—C12—C11119.0 (4)
O6iv—Eu1—N3145.36 (8)C13—C12—H12120.5
O4—Eu1—N373.30 (9)C11—C12—H12120.5
N2—Eu1—N361.68 (9)C14—C13—C12119.2 (4)
N1—Eu1—N3118.75 (9)C14—C13—H13120.4
O1i—Eu1—O5122.88 (8)C12—C13—H13120.4
O5ii—Eu1—O573.15 (9)C13—C14—C15119.5 (4)
O7iii—Eu1—O570.14 (9)C13—C14—H14120.2
O6iv—Eu1—O571.88 (8)C15—C14—H14120.2
O4—Eu1—O549.83 (8)N3—C15—C14122.2 (4)
N2—Eu1—O5145.58 (8)N3—C15—H15118.9
N1—Eu1—O5140.72 (8)C14—C15—H15118.9
N3—Eu1—O5100.19 (9)C17—C16—C21117.1 (4)
O1i—Eu1—Eu1ii144.58 (6)C17—C16—C8117.2 (4)
O5ii—Eu1—Eu1ii39.37 (6)C21—C16—C8125.7 (4)
O7iii—Eu1—Eu1ii66.16 (6)C16—C17—C18122.5 (4)
O6iv—Eu1—Eu1ii68.02 (6)C16—C17—H17118.8
O4—Eu1—Eu1ii82.75 (6)C18—C17—H17118.8
N2—Eu1—Eu1ii130.63 (6)C19—C18—C17119.8 (4)
N1—Eu1—Eu1ii110.82 (6)C19—C18—H18120.1
N3—Eu1—Eu1ii123.40 (7)C17—C18—H18120.1
O5—Eu1—Eu1ii33.78 (5)C18—C19—C20119.2 (4)
O3—S1—O2115.07 (18)C18—C19—H19120.4
O3—S1—O1111.16 (16)C20—C19—H19120.4
O2—S1—O1112.07 (16)C19—C20—C21122.1 (4)
O3—S1—C21108.38 (17)C19—C20—H20118.9
O2—S1—C21105.46 (18)C21—C20—H20118.9
O1—S1—C21103.84 (17)C20—C21—C16119.3 (4)
C1—N1—C5117.6 (3)C20—C21—S1115.1 (3)
C1—N1—Eu1121.0 (2)C16—C21—S1125.6 (3)
C5—N1—Eu1121.4 (2)O4—C22—O5120.0 (3)
C10—N2—C6117.6 (3)O4—C22—C23120.3 (3)
C10—N2—Eu1118.9 (2)O5—C22—C23119.7 (3)
C6—N2—Eu1121.3 (2)C22—C23—C24114.1 (3)
C11—N3—C15117.7 (3)C22—C23—H23A108.7
C11—N3—Eu1117.6 (2)C24—C23—H23A108.7
C15—N3—Eu1123.7 (2)C22—C23—H23B108.7
S1—O1—Eu1iii153.67 (15)C24—C23—H23B108.7
C22—O4—Eu1102.0 (2)H23A—C23—H23B107.6
C22—O5—Eu1ii156.7 (2)C23—C24—C25115.5 (3)
C22—O5—Eu187.9 (2)C23—C24—H24A108.4
Eu1ii—O5—Eu1106.85 (9)C25—C24—H24A108.4
C26—O6—Eu1v135.8 (2)C23—C24—H24B108.4
C26—O7—Eu1i139.5 (2)C25—C24—H24B108.4
N1—C1—C2124.0 (4)H24A—C24—H24B107.5
N1—C1—H1118.0C24—C25—C26114.1 (3)
C2—C1—H1118.0C24—C25—H25A108.7
C3—C2—C1118.0 (4)C26—C25—H25A108.7
C3—C2—H2121.0C24—C25—H25B108.7
C1—C2—H2121.0C26—C25—H25B108.7
C2—C3—C4119.3 (4)H25A—C25—H25B107.6
C2—C3—H3120.4O7—C26—O6125.7 (3)
C4—C3—H3120.4O7—C26—C25116.6 (3)
C3—C4—C5119.3 (4)O6—C26—C25117.6 (3)
O3—S1—O1—Eu1iii161.9 (3)C10—C11—C12—C13173.7 (4)
O2—S1—O1—Eu1iii31.5 (4)C11—C12—C13—C142.1 (8)
C21—S1—O1—Eu1iii81.8 (4)C12—C13—C14—C153.0 (9)
C5—N1—C1—C21.8 (6)C11—N3—C15—C140.2 (7)
Eu1—N1—C1—C2177.4 (3)Eu1—N3—C15—C14167.6 (4)
N1—C1—C2—C30.8 (7)C13—C14—C15—N31.9 (9)
C1—C2—C3—C40.0 (7)C9—C8—C16—C17141.5 (4)
C2—C3—C4—C50.3 (7)C7—C8—C16—C1736.8 (6)
C1—N1—C5—C42.1 (6)C9—C8—C16—C2138.5 (6)
Eu1—N1—C5—C4177.2 (3)C7—C8—C16—C21143.2 (4)
C1—N1—C5—C6176.6 (3)C21—C16—C17—C182.8 (7)
Eu1—N1—C5—C64.1 (4)C8—C16—C17—C18177.2 (5)
C3—C4—C5—N11.3 (7)C16—C17—C18—C190.2 (8)
C3—C4—C5—C6177.3 (4)C17—C18—C19—C202.0 (9)
C10—N2—C6—C71.1 (5)C18—C19—C20—C211.5 (8)
Eu1—N2—C6—C7162.2 (3)C19—C20—C21—C161.2 (7)
C10—N2—C6—C5176.4 (3)C19—C20—C21—S1179.9 (4)
Eu1—N2—C6—C520.2 (4)C17—C16—C21—C203.2 (6)
N1—C5—C6—N210.2 (5)C8—C16—C21—C20176.8 (4)
C4—C5—C6—N2168.5 (4)C17—C16—C21—S1178.0 (3)
N1—C5—C6—C7172.3 (3)C8—C16—C21—S11.9 (6)
C4—C5—C6—C79.0 (6)O3—S1—C21—C20144.9 (3)
N2—C6—C7—C84.5 (6)O2—S1—C21—C2021.1 (4)
C5—C6—C7—C8178.1 (4)O1—S1—C21—C2096.9 (3)
C6—C7—C8—C93.9 (6)O3—S1—C21—C1636.3 (4)
C6—C7—C8—C16174.5 (4)O2—S1—C21—C16160.0 (4)
C7—C8—C9—C102.1 (6)O1—S1—C21—C1682.0 (4)
C16—C8—C9—C10179.5 (4)Eu1—O4—C22—O56.1 (4)
C6—N2—C10—C97.4 (5)Eu1—O4—C22—C23174.6 (3)
Eu1—N2—C10—C9156.4 (3)Eu1ii—O5—C22—O4135.7 (5)
C6—N2—C10—C11167.4 (3)Eu1—O5—C22—O45.4 (3)
Eu1—N2—C10—C1128.8 (4)Eu1ii—O5—C22—C2345.1 (8)
C8—C9—C10—N28.1 (6)Eu1—O5—C22—C23175.4 (3)
C8—C9—C10—C11166.5 (3)O4—C22—C23—C245.7 (6)
C15—N3—C11—C121.1 (6)O5—C22—C23—C24173.6 (3)
Eu1—N3—C11—C12167.5 (3)C22—C23—C24—C25177.5 (4)
C15—N3—C11—C10172.9 (3)C23—C24—C25—C26172.5 (4)
Eu1—N3—C11—C1018.6 (4)Eu1i—O7—C26—O629.2 (7)
N2—C10—C11—N35.9 (5)Eu1i—O7—C26—C25148.5 (3)
C9—C10—C11—N3179.2 (3)Eu1v—O6—C26—O728.9 (6)
N2—C10—C11—C12168.1 (4)Eu1v—O6—C26—C25148.8 (3)
C9—C10—C11—C126.7 (6)C24—C25—C26—O737.6 (5)
N3—C11—C12—C130.0 (7)C24—C25—C26—O6144.6 (4)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y+1, z+1; (iii) x, y+1/2, z1/2; (iv) x+1, y+1/2, z+3/2; (v) x+1, y1/2, z+3/2.
(2) top
Crystal data top
C67H58Er4N6O30S2F(000) = 4184
Mr = 2160.35Dx = 2.010 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 39.336 (4) ÅCell parameters from 3921 reflections
b = 8.6380 (9) Åθ = 2.4–25.9°
c = 25.594 (3) ŵ = 4.81 mm1
β = 124.837 (2)°T = 296 K
V = 7137.9 (13) Å3Block, pink
Z = 40.14 × 0.10 × 0.08 mm
Data collection top
Bruker APEX-II CCD
diffractometer
5082 reflections with I > 2σ(I)
φ and ω scansRint = 0.039
Absorption correction: multi-scan
sadabs
θmax = 25.1°, θmin = 2.4°
Tmin = 0.565, Tmax = 0.682h = 4638
17352 measured reflectionsk = 1010
6309 independent reflectionsl = 1930
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.067 w = 1/[σ2(Fo2) + (0.0234P)2 + 3.6022P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
6309 reflectionsΔρmax = 0.93 e Å3
492 parametersΔρmin = 0.79 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*/UeqOcc. (<1)
Er10.13567 (2)0.45805 (3)0.28112 (2)0.02142 (7)
Er20.03409 (2)0.44330 (3)0.08917 (2)0.02384 (8)
S10.25395 (4)0.11417 (17)0.61042 (7)0.0341 (4)
N10.17043 (13)0.6892 (5)0.3490 (2)0.0277 (11)
N20.15565 (12)0.4299 (5)0.3911 (2)0.0265 (10)
N30.11122 (13)0.2171 (5)0.3018 (2)0.0296 (11)
O10.29640 (11)0.0957 (5)0.66815 (17)0.0402 (10)
O20.22943 (14)0.0204 (5)0.5986 (3)0.0730 (17)
O30.25373 (14)0.1681 (6)0.5572 (2)0.0622 (14)
O40.12974 (12)0.6221 (4)0.20973 (18)0.0393 (10)
O50.08189 (12)0.6182 (5)0.10559 (18)0.0409 (10)
O60.13844 (12)1.2844 (4)0.21811 (18)0.0385 (10)
O70.08943 (11)1.2988 (4)0.11442 (18)0.0395 (10)
O80.01226 (12)0.6829 (4)0.10906 (17)0.0428 (11)
O90.01047 (11)0.6339 (4)0.01072 (16)0.0344 (9)
O100.01510 (11)1.1916 (4)0.09701 (19)0.0388 (10)
O110.03144 (11)1.3740 (4)0.06336 (19)0.0410 (10)
O120.06100 (11)0.4395 (4)0.19521 (17)0.0326 (9)
O130.08085 (12)0.5644 (4)0.28229 (19)0.0415 (11)
C10.17766 (17)0.8157 (6)0.3261 (3)0.0378 (15)
H10.16990.81430.28430.045*
C20.19627 (19)0.9483 (7)0.3622 (3)0.0456 (17)
H20.20041.03420.34450.055*
C30.20845 (17)0.9507 (7)0.4242 (3)0.0386 (15)
H30.22111.03770.44950.046*
C40.20142 (16)0.8192 (6)0.4481 (3)0.0335 (14)
H40.20890.81840.48980.040*
C50.18322 (15)0.6893 (6)0.4101 (2)0.0284 (13)
C60.17631 (16)0.5432 (6)0.4336 (2)0.0268 (12)
C70.19161 (17)0.5256 (6)0.4980 (3)0.0312 (13)
H70.20480.60790.52600.037*
C80.18704 (15)0.3864 (6)0.5195 (2)0.0269 (12)
C90.16536 (15)0.2696 (6)0.4750 (2)0.0296 (13)
H90.16160.17430.48790.036*
C100.14940 (15)0.2953 (6)0.4115 (2)0.0257 (12)
C110.12420 (15)0.1783 (6)0.3621 (2)0.0271 (12)
C120.11342 (17)0.0363 (6)0.3751 (3)0.0322 (13)
H120.12250.01120.41650.039*
C130.08924 (18)0.0662 (6)0.3260 (3)0.0383 (15)
H130.08210.16140.33410.046*
C140.07575 (19)0.0265 (7)0.2649 (3)0.0417 (16)
H140.05940.09390.23110.050*
C150.08704 (17)0.1155 (7)0.2551 (3)0.0379 (15)
H150.07730.14290.21360.046*
C160.20392 (16)0.3728 (6)0.5892 (2)0.0286 (13)
C170.18963 (19)0.4820 (7)0.6117 (3)0.0422 (16)
H170.17020.55440.58370.051*
C180.20376 (18)0.4856 (7)0.6751 (3)0.0424 (16)
H180.19330.55900.68900.051*
C190.23311 (18)0.3818 (7)0.7177 (3)0.0423 (16)
H190.24290.38480.76050.051*
C200.24754 (17)0.2740 (7)0.6959 (3)0.0356 (14)
H200.26790.20530.72480.043*
C210.23289 (15)0.2630 (6)0.6321 (2)0.0248 (12)
C220.11389 (17)0.6720 (6)0.1533 (3)0.0298 (13)
C230.13497 (18)0.8067 (6)0.1456 (3)0.0354 (14)
H23A0.13100.80110.10460.042*
H23B0.16450.80420.17870.042*
C240.11627 (18)0.9551 (6)0.1504 (3)0.0372 (15)
H24A0.11710.95290.18900.045*
H24B0.08750.96130.11450.045*
C250.13929 (17)1.0993 (6)0.1510 (3)0.0331 (14)
H25A0.16861.09060.18460.040*
H25B0.13621.10880.11070.040*
C260.12153 (16)1.2389 (6)0.1619 (3)0.0258 (12)
C270.00833 (16)0.7252 (6)0.0524 (3)0.0306 (13)
C280.02864 (18)0.8809 (6)0.0335 (3)0.0360 (14)
H28A0.05460.87240.00820.043*
H28B0.01100.95180.02980.043*
C290.03737 (19)0.9490 (6)0.0794 (3)0.0399 (15)
H29A0.01210.94690.12210.048*
H29B0.05770.88520.07910.048*
C300.05337 (18)1.1155 (6)0.0626 (3)0.0448 (16)
H30A0.07621.11960.01790.054*
H30B0.06411.14430.08710.054*
C310.02105 (18)1.2326 (7)0.0748 (3)0.0343 (14)
C320.05229 (19)0.5087 (7)0.2308 (3)0.0394 (15)
C330.0083 (2)0.5060 (14)0.2105 (4)0.109 (4)
H33A0.00110.40070.21360.130*
H33B0.00950.53690.16620.130*
C340.00000.6119 (17)0.25000.145 (7)
H34A0.02380.67740.27770.174*0.5
H34B0.02380.67740.22230.174*0.5
O140.14412 (15)0.8849 (6)0.5144 (2)0.0802 (16)
O150.90320 (16)0.6006 (7)0.9995 (4)0.123 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Er10.02235 (13)0.02192 (13)0.01507 (13)0.00158 (10)0.00778 (11)0.00118 (10)
Er20.02549 (14)0.02409 (13)0.01544 (13)0.00013 (10)0.00786 (11)0.00048 (10)
S10.0281 (8)0.0377 (8)0.0263 (8)0.0060 (7)0.0096 (7)0.0031 (7)
N10.031 (3)0.024 (2)0.024 (3)0.000 (2)0.013 (2)0.002 (2)
N20.020 (2)0.032 (3)0.022 (2)0.0001 (19)0.008 (2)0.006 (2)
N30.033 (3)0.027 (2)0.020 (2)0.001 (2)0.010 (2)0.001 (2)
O10.027 (2)0.056 (3)0.025 (2)0.0107 (19)0.0078 (18)0.0001 (19)
O20.050 (3)0.041 (3)0.106 (5)0.011 (2)0.032 (3)0.025 (3)
O30.067 (3)0.096 (4)0.036 (3)0.039 (3)0.036 (3)0.015 (3)
O40.049 (3)0.036 (2)0.030 (2)0.004 (2)0.021 (2)0.0067 (19)
O50.036 (2)0.043 (2)0.031 (2)0.006 (2)0.012 (2)0.004 (2)
O60.044 (2)0.038 (2)0.032 (2)0.0068 (19)0.020 (2)0.0025 (19)
O70.037 (2)0.044 (2)0.030 (2)0.0096 (19)0.014 (2)0.0007 (19)
O80.053 (3)0.042 (2)0.019 (2)0.011 (2)0.012 (2)0.0006 (18)
O90.043 (2)0.032 (2)0.021 (2)0.0002 (19)0.0143 (19)0.0040 (17)
O100.032 (2)0.036 (2)0.044 (3)0.0016 (18)0.018 (2)0.0020 (19)
O110.042 (2)0.028 (2)0.051 (3)0.0029 (19)0.026 (2)0.004 (2)
O120.034 (2)0.040 (2)0.023 (2)0.0003 (18)0.0160 (19)0.0012 (18)
O130.030 (2)0.052 (3)0.033 (2)0.0033 (19)0.013 (2)0.010 (2)
C10.043 (4)0.038 (4)0.028 (3)0.005 (3)0.018 (3)0.001 (3)
C20.044 (4)0.037 (4)0.046 (4)0.010 (3)0.020 (3)0.001 (3)
C30.033 (3)0.038 (4)0.041 (4)0.005 (3)0.018 (3)0.013 (3)
C40.036 (3)0.029 (3)0.030 (3)0.002 (3)0.015 (3)0.005 (3)
C50.025 (3)0.030 (3)0.021 (3)0.001 (2)0.007 (3)0.001 (2)
C60.029 (3)0.028 (3)0.021 (3)0.004 (2)0.013 (3)0.001 (2)
C70.032 (3)0.036 (3)0.024 (3)0.007 (3)0.015 (3)0.003 (3)
C80.025 (3)0.031 (3)0.021 (3)0.007 (2)0.011 (3)0.004 (2)
C90.030 (3)0.030 (3)0.025 (3)0.003 (2)0.013 (3)0.003 (2)
C100.022 (3)0.027 (3)0.021 (3)0.007 (2)0.008 (2)0.002 (2)
C110.023 (3)0.033 (3)0.023 (3)0.000 (2)0.011 (3)0.001 (2)
C120.036 (3)0.036 (3)0.030 (3)0.001 (3)0.022 (3)0.004 (3)
C130.046 (4)0.032 (3)0.040 (4)0.009 (3)0.027 (3)0.003 (3)
C140.046 (4)0.034 (3)0.040 (4)0.014 (3)0.021 (3)0.009 (3)
C150.037 (3)0.043 (4)0.029 (3)0.004 (3)0.017 (3)0.003 (3)
C160.028 (3)0.032 (3)0.025 (3)0.003 (2)0.014 (3)0.003 (2)
C170.047 (4)0.043 (4)0.030 (3)0.014 (3)0.018 (3)0.002 (3)
C180.044 (4)0.048 (4)0.033 (4)0.005 (3)0.020 (3)0.013 (3)
C190.041 (4)0.060 (4)0.022 (3)0.000 (3)0.015 (3)0.004 (3)
C200.034 (3)0.039 (3)0.022 (3)0.004 (3)0.009 (3)0.002 (3)
C210.024 (3)0.029 (3)0.020 (3)0.003 (2)0.012 (2)0.004 (2)
C220.035 (3)0.028 (3)0.030 (3)0.002 (3)0.021 (3)0.001 (3)
C230.041 (4)0.033 (3)0.043 (4)0.004 (3)0.031 (3)0.001 (3)
C240.048 (4)0.025 (3)0.043 (4)0.004 (3)0.028 (3)0.004 (3)
C250.036 (3)0.027 (3)0.035 (3)0.000 (3)0.020 (3)0.001 (3)
C260.032 (3)0.023 (3)0.025 (3)0.010 (2)0.017 (3)0.002 (2)
C270.031 (3)0.034 (3)0.023 (3)0.010 (3)0.013 (3)0.003 (3)
C280.039 (3)0.033 (3)0.024 (3)0.004 (3)0.011 (3)0.002 (3)
C290.045 (4)0.033 (3)0.051 (4)0.004 (3)0.033 (3)0.003 (3)
C300.044 (4)0.037 (4)0.064 (5)0.001 (3)0.037 (4)0.007 (3)
C310.041 (4)0.033 (3)0.027 (3)0.003 (3)0.018 (3)0.004 (3)
C320.035 (4)0.051 (4)0.030 (4)0.007 (3)0.018 (3)0.007 (3)
C330.040 (5)0.249 (13)0.038 (5)0.003 (6)0.023 (4)0.037 (6)
C340.072 (10)0.094 (11)0.23 (2)0.0000.065 (13)0.000
O140.070 (3)0.099 (4)0.070 (4)0.008 (3)0.039 (3)0.030 (3)
O150.055 (4)0.102 (5)0.178 (7)0.001 (3)0.046 (4)0.013 (5)
Geometric parameters (Å, º) top
Er1—O42.217 (4)C7—C81.377 (7)
Er1—O6i2.250 (4)C7—H70.9300
Er1—O1ii2.254 (4)C8—C91.391 (7)
Er1—O132.359 (4)C8—C161.510 (7)
Er1—N22.463 (4)C9—C101.386 (7)
Er1—O122.472 (4)C9—H90.9300
Er1—N32.473 (4)C10—C111.473 (7)
Er1—N12.482 (4)C11—C121.399 (7)
Er2—O52.256 (4)C12—C131.379 (7)
Er2—O7i2.260 (4)C12—H120.9300
Er2—O9iii2.265 (4)C13—C141.377 (8)
Er2—O122.282 (4)C13—H130.9300
Er2—O11i2.344 (4)C14—C151.376 (8)
Er2—O10i2.345 (4)C14—H140.9300
Er2—O82.404 (4)C15—H150.9300
Er2—O92.407 (4)C16—C171.380 (7)
Er2—C31i2.691 (6)C16—C211.405 (7)
Er2—Er2iii3.8731 (6)C17—C181.385 (8)
S1—O21.428 (5)C17—H170.9300
S1—O31.435 (4)C18—C191.374 (8)
S1—O11.476 (4)C18—H180.9300
S1—C211.781 (5)C19—C201.365 (8)
N1—C51.340 (6)C19—H190.9300
N1—C11.345 (6)C20—C211.391 (7)
N2—C61.339 (6)C20—H200.9300
N2—C101.353 (6)C22—C231.506 (7)
N3—C151.343 (6)C23—C241.517 (7)
N3—C111.362 (6)C23—H23A0.9700
O1—Er1ii2.254 (4)C23—H23B0.9700
O4—C221.277 (6)C24—C251.535 (7)
O5—C221.240 (6)C24—H24A0.9700
O6—C261.254 (6)C24—H24B0.9700
O6—Er1iv2.250 (4)C25—C261.497 (7)
O7—C261.259 (6)C25—H25A0.9700
O7—Er2iv2.260 (4)C25—H25B0.9700
O8—C271.245 (6)C27—C281.496 (7)
O9—C271.290 (6)C28—C291.519 (8)
O9—Er2iii2.265 (4)C28—H28A0.9700
O10—C311.244 (6)C28—H28B0.9700
O10—Er2iv2.345 (4)C29—C301.529 (7)
O11—C311.268 (6)C29—H29A0.9700
O11—Er2iv2.344 (4)C29—H29B0.9700
O12—C321.288 (7)C30—C311.511 (7)
O13—C321.241 (7)C30—H30A0.9700
C1—C21.388 (8)C30—H30B0.9700
C1—H10.9300C31—Er2iv2.691 (6)
C2—C31.371 (8)C32—C331.494 (9)
C2—H20.9300C33—C341.532 (11)
C3—C41.391 (8)C33—H33A0.9700
C3—H30.9300C33—H33B0.9700
C4—C51.387 (7)C34—C33v1.532 (11)
C4—H40.9300C34—H34A0.9700
C5—C61.489 (7)C34—H34B0.9700
C6—C71.402 (7)
O4—Er1—O6i82.00 (14)N1—C5—C6115.9 (5)
O4—Er1—O1ii97.95 (14)C4—C5—C6122.8 (5)
O6i—Er1—O1ii75.44 (14)N2—C6—C7122.0 (5)
O4—Er1—O1395.45 (14)N2—C6—C5117.2 (5)
O6i—Er1—O13133.42 (13)C7—C6—C5120.8 (5)
O1ii—Er1—O13149.81 (13)C8—C7—C6119.9 (5)
O4—Er1—N2145.02 (14)C8—C7—H7120.0
O6i—Er1—N2129.66 (14)C6—C7—H7120.0
O1ii—Er1—N279.74 (14)C7—C8—C9117.6 (5)
O13—Er1—N273.84 (14)C7—C8—C16118.1 (5)
O4—Er1—O1278.24 (13)C9—C8—C16124.1 (5)
O6i—Er1—O1280.72 (13)C10—C9—C8120.0 (5)
O1ii—Er1—O12156.16 (13)C10—C9—H9120.0
O13—Er1—O1253.59 (13)C8—C9—H9120.0
N2—Er1—O12116.83 (13)N2—C10—C9122.0 (5)
O4—Er1—N3147.50 (14)N2—C10—C11116.1 (5)
O6i—Er1—N377.05 (14)C9—C10—C11121.9 (5)
O1ii—Er1—N3100.45 (14)N3—C11—C12121.1 (5)
O13—Er1—N381.68 (14)N3—C11—C10115.9 (5)
N2—Er1—N365.30 (14)C12—C11—C10123.0 (5)
O12—Er1—N374.10 (12)C13—C12—C11119.4 (5)
O4—Er1—N179.58 (14)C13—C12—H12120.3
O6i—Er1—N1143.61 (14)C11—C12—H12120.3
O1ii—Er1—N176.38 (14)C14—C13—C12119.5 (5)
O13—Er1—N179.63 (14)C14—C13—H13120.2
N2—Er1—N165.87 (14)C12—C13—H13120.2
O12—Er1—N1125.06 (13)C15—C14—C13118.3 (5)
N3—Er1—N1130.80 (14)C15—C14—H14120.9
O5—Er2—O7i75.68 (15)C13—C14—H14120.9
O5—Er2—O9iii99.68 (14)N3—C15—C14124.0 (5)
O7i—Er2—O9iii82.37 (13)N3—C15—H15118.0
O5—Er2—O1290.98 (13)C14—C15—H15118.0
O7i—Er2—O1286.30 (13)C17—C16—C21118.5 (5)
O9iii—Er2—O12161.98 (13)C17—C16—C8115.4 (5)
O5—Er2—O11i152.70 (14)C21—C16—C8126.0 (5)
O7i—Er2—O11i131.61 (14)C16—C17—C18121.2 (6)
O9iii—Er2—O11i86.03 (14)C16—C17—H17119.4
O12—Er2—O11i91.13 (14)C18—C17—H17119.4
O5—Er2—O10i151.32 (14)C19—C18—C17120.6 (6)
O7i—Er2—O10i76.42 (14)C19—C18—H18119.7
O9iii—Er2—O10i83.01 (14)C17—C18—H18119.7
O12—Er2—O10i80.73 (13)C20—C19—C18118.5 (6)
O11i—Er2—O10i55.56 (13)C20—C19—H19120.7
O5—Er2—O875.21 (14)C18—C19—H19120.7
O7i—Er2—O8144.81 (13)C19—C20—C21122.5 (5)
O9iii—Er2—O8121.77 (13)C19—C20—H20118.8
O12—Er2—O874.90 (13)C21—C20—H20118.8
O11i—Er2—O879.11 (14)C20—C21—C16118.6 (5)
O10i—Er2—O8127.61 (14)C20—C21—S1117.4 (4)
O5—Er2—O980.20 (13)C16—C21—S1123.9 (4)
O7i—Er2—O9137.73 (13)O5—C22—O4123.6 (5)
O9iii—Er2—O968.03 (15)O5—C22—C23119.1 (5)
O12—Er2—O9128.61 (12)O4—C22—C23117.3 (5)
O11i—Er2—O977.28 (13)C22—C23—C24108.3 (4)
O10i—Er2—O9126.14 (13)C22—C23—H23A110.0
O8—Er2—O953.83 (12)C24—C23—H23A110.0
O5—Er2—C31i177.65 (15)C22—C23—H23B110.0
O7i—Er2—C31i103.59 (16)C24—C23—H23B110.0
O9iii—Er2—C31i82.38 (15)H23A—C23—H23B108.4
O12—Er2—C31i86.74 (15)C23—C24—C25112.1 (5)
O11i—Er2—C31i28.11 (15)C23—C24—H24A109.2
O10i—Er2—C31i27.52 (14)C25—C24—H24A109.2
O8—Er2—C31i104.70 (16)C23—C24—H24B109.2
O9—Er2—C31i101.67 (15)C25—C24—H24B109.2
O5—Er2—Er2iii89.58 (10)H24A—C24—H24B107.9
O7i—Er2—Er2iii112.47 (10)C26—C25—C24108.7 (4)
O9iii—Er2—Er2iii35.19 (9)C26—C25—H25A110.0
O12—Er2—Er2iii160.71 (9)C24—C25—H25A110.0
O11i—Er2—Er2iii79.78 (10)C26—C25—H25B110.0
O10i—Er2—Er2iii107.18 (10)C24—C25—H25B110.0
O8—Er2—Er2iii86.63 (9)H25A—C25—H25B108.3
O9—Er2—Er2iii32.84 (8)O6—C26—O7124.1 (5)
C31i—Er2—Er2iii92.76 (12)O6—C26—C25117.9 (5)
O2—S1—O3115.2 (3)O7—C26—C25117.9 (5)
O2—S1—O1111.4 (3)O8—C27—O9118.4 (5)
O3—S1—O1112.1 (3)O8—C27—C28120.9 (5)
O2—S1—C21106.0 (3)O9—C27—C28120.7 (5)
O3—S1—C21108.0 (3)C27—C28—C29114.4 (5)
O1—S1—C21103.2 (2)C27—C28—H28A108.7
C5—N1—C1118.4 (5)C29—C28—H28A108.7
C5—N1—Er1120.4 (3)C27—C28—H28B108.7
C1—N1—Er1121.2 (3)C29—C28—H28B108.7
C6—N2—C10118.3 (5)H28A—C28—H28B107.6
C6—N2—Er1120.4 (3)C28—C29—C30112.7 (5)
C10—N2—Er1121.1 (3)C28—C29—H29A109.1
C15—N3—C11117.6 (5)C30—C29—H29A109.1
C15—N3—Er1121.6 (4)C28—C29—H29B109.1
C11—N3—Er1120.6 (3)C30—C29—H29B109.1
S1—O1—Er1ii152.9 (3)H29A—C29—H29B107.8
C22—O4—Er1154.3 (4)C31—C30—C29114.1 (5)
C22—O5—Er2134.7 (4)C31—C30—H30A108.7
C26—O6—Er1iv145.1 (4)C29—C30—H30A108.7
C26—O7—Er2iv140.7 (4)C31—C30—H30B108.7
C27—O8—Er294.6 (3)C29—C30—H30B108.7
C27—O9—Er2iii154.7 (4)H30A—C30—H30B107.6
C27—O9—Er293.2 (3)O10—C31—O11120.9 (5)
Er2iii—O9—Er2111.97 (15)O10—C31—C30120.7 (5)
C31—O10—Er2iv91.9 (3)O11—C31—C30118.4 (5)
C31—O11—Er2iv91.3 (3)O10—C31—Er2iv60.6 (3)
C32—O12—Er2134.7 (4)O11—C31—Er2iv60.6 (3)
C32—O12—Er190.1 (3)C30—C31—Er2iv176.7 (4)
Er2—O12—Er1124.42 (16)O13—C32—O12119.1 (6)
C32—O13—Er196.6 (4)O13—C32—C33122.7 (6)
N1—C1—C2122.9 (6)O12—C32—C33118.0 (6)
N1—C1—H1118.6C32—C33—C34113.8 (6)
C2—C1—H1118.6C32—C33—H33A108.8
C3—C2—C1119.0 (6)C34—C33—H33A108.8
C3—C2—H2120.5C32—C33—H33B108.8
C1—C2—H2120.5C34—C33—H33B108.8
C2—C3—C4118.1 (5)H33A—C33—H33B107.7
C2—C3—H3120.9C33v—C34—C33106.7 (12)
C4—C3—H3120.9C33v—C34—H34A110.4
C5—C4—C3120.3 (5)C33—C34—H34A110.4
C5—C4—H4119.9C33v—C34—H34B110.4
C3—C4—H4119.9C33—C34—H34B110.4
N1—C5—C4121.2 (5)H34A—C34—H34B108.6
O2—S1—O1—Er1ii98.8 (6)C16—C17—C18—C191.2 (10)
O3—S1—O1—Er1ii32.0 (7)C17—C18—C19—C200.9 (10)
C21—S1—O1—Er1ii147.9 (5)C18—C19—C20—C211.7 (9)
C5—N1—C1—C22.7 (8)C19—C20—C21—C163.8 (9)
Er1—N1—C1—C2178.7 (4)C19—C20—C21—S1178.8 (5)
N1—C1—C2—C31.0 (9)C17—C16—C21—C203.3 (8)
C1—C2—C3—C40.2 (9)C8—C16—C21—C20175.2 (5)
C2—C3—C4—C51.1 (8)C17—C16—C21—S1179.5 (4)
C1—N1—C5—C43.6 (8)C8—C16—C21—S12.0 (8)
Er1—N1—C5—C4177.8 (4)O2—S1—C21—C2086.9 (5)
C1—N1—C5—C6176.9 (5)O3—S1—C21—C20149.1 (4)
Er1—N1—C5—C61.7 (6)O1—S1—C21—C2030.3 (5)
C3—C4—C5—N12.9 (8)O2—S1—C21—C1695.9 (5)
C3—C4—C5—C6177.7 (5)O3—S1—C21—C1628.1 (5)
C10—N2—C6—C70.4 (8)O1—S1—C21—C16146.9 (5)
Er1—N2—C6—C7173.9 (4)Er2—O5—C22—O46.8 (9)
C10—N2—C6—C5179.3 (4)Er2—O5—C22—C23171.2 (4)
Er1—N2—C6—C55.0 (6)Er1—O4—C22—O59.5 (12)
N1—C5—C6—N24.4 (7)Er1—O4—C22—C23172.4 (6)
C4—C5—C6—N2175.1 (5)O5—C22—C23—C2488.4 (6)
N1—C5—C6—C7174.5 (5)O4—C22—C23—C2489.8 (6)
C4—C5—C6—C76.0 (8)C22—C23—C24—C25173.2 (5)
N2—C6—C7—C82.7 (8)C23—C24—C25—C26174.7 (5)
C5—C6—C7—C8176.2 (5)Er1iv—O6—C26—O70.7 (10)
C6—C7—C8—C92.9 (8)Er1iv—O6—C26—C25177.2 (4)
C6—C7—C8—C16179.9 (5)Er2iv—O7—C26—O622.1 (9)
C7—C8—C9—C100.3 (8)Er2iv—O7—C26—C25154.4 (4)
C16—C8—C9—C10177.1 (5)C24—C25—C26—O692.7 (6)
C6—N2—C10—C93.1 (7)C24—C25—C26—O784.0 (6)
Er1—N2—C10—C9171.1 (4)Er2—O8—C27—O91.7 (5)
C6—N2—C10—C11176.2 (4)Er2—O8—C27—C28175.8 (5)
Er1—N2—C10—C119.7 (6)Er2iii—O9—C27—O8172.9 (5)
C8—C9—C10—N22.8 (8)Er2—O9—C27—O81.7 (5)
C8—C9—C10—C11176.4 (5)Er2iii—O9—C27—C289.6 (12)
C15—N3—C11—C121.3 (8)Er2—O9—C27—C28175.8 (5)
Er1—N3—C11—C12174.5 (4)O8—C27—C28—C2923.9 (8)
C15—N3—C11—C10177.9 (5)O9—C27—C28—C29158.6 (5)
Er1—N3—C11—C106.3 (6)C27—C28—C29—C30173.2 (5)
N2—C10—C11—N32.1 (7)C28—C29—C30—C3171.1 (7)
C9—C10—C11—N3178.6 (5)Er2iv—O10—C31—O115.4 (6)
N2—C10—C11—C12177.0 (5)Er2iv—O10—C31—C30176.5 (5)
C9—C10—C11—C122.2 (8)Er2iv—O11—C31—O105.4 (6)
N3—C11—C12—C130.0 (8)Er2iv—O11—C31—C30176.4 (5)
C10—C11—C12—C13179.1 (5)C29—C30—C31—O100.4 (8)
C11—C12—C13—C140.7 (9)C29—C30—C31—O11178.6 (5)
C12—C13—C14—C150.0 (9)Er1—O13—C32—O128.2 (6)
C11—N3—C15—C142.1 (8)Er1—O13—C32—C33166.2 (7)
Er1—N3—C15—C14173.7 (4)Er2—O12—C32—O13135.1 (5)
C13—C14—C15—N31.4 (9)Er1—O12—C32—O137.8 (6)
C7—C8—C16—C1755.2 (7)Er2—O12—C32—C3350.2 (9)
C9—C8—C16—C17121.6 (6)Er1—O12—C32—C33166.9 (6)
C7—C8—C16—C21123.3 (6)O13—C32—C33—C3414.5 (12)
C9—C8—C16—C2159.9 (8)O12—C32—C33—C34171.0 (7)
C21—C16—C17—C180.9 (9)C32—C33—C34—C33v110.5 (8)
C8—C16—C17—C18177.8 (5)
Symmetry codes: (i) x, y1, z; (ii) x+1/2, y+1/2, z+1; (iii) x, y+1, z; (iv) x, y+1, z; (v) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C33—H33B···O11i0.972.663.346 (9)128
C33—H33B···O80.972.433.091 (11)125
C28—H28B···O100.972.513.100 (7)119
C25—H25B···O14vi0.972.663.612 (8)168
C15—H15···O120.932.623.072 (7)111
C15—H15···O10i0.932.593.425 (7)149
C12—H12···O14i0.932.403.310 (7)166
C1—H1···O40.932.332.967 (7)125
C33—H33B···O80.972.433.091 (11)125
C28—H28B···O100.972.513.100 (7)119
C15—H15···O120.932.623.072 (7)111
C15—H15···O10i0.932.593.425 (7)149
C12—H12···O14i0.932.403.310 (7)166
C1—H1···O40.932.332.967 (7)125
C1—H1···O40.932.332.967 (7)125
C12—H12···O14i0.932.403.310 (7)166
C15—H15···O10i0.932.593.425 (7)149
C15—H15···O120.932.623.072 (7)111
C25—H25B···O14vi0.972.663.612 (8)168
C28—H28B···O100.972.513.100 (7)119
C33—H33B···O80.972.433.091 (11)125
C1—H1···O40.932.332.967 (7)125
C12—H12···O14i0.932.403.310 (7)166
C15—H15···O10i0.932.593.425 (7)149
C15—H15···O120.932.623.072 (7)111
C25—H25B···O14vi0.972.663.612 (8)168
C28—H28B···O100.972.513.100 (7)119
C33—H33B···O80.972.433.091 (11)125
C33—H33B···O11i0.972.663.346 (9)128
Symmetry codes: (i) x, y1, z; (vi) x, y+2, z1/2.
(3) top
Crystal data top
C67H58N6O26S2Yb4·4(O)F(000) = 4216
Mr = 2183.47Dx = 2.016 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 39.474 (8) ÅCell parameters from 2917 reflections
b = 8.6567 (17) Åθ = 2.4–25.3°
c = 25.670 (5) ŵ = 5.30 mm1
β = 124.895 (2)°T = 296 K
V = 7195 (2) Å3Block, yellow
Z = 40.12 × 0.10 × 0.08 mm
Data collection top
Bruker APEX-II CCD
diffractometer
4703 reflections with I > 2σ(I)
φ and ω scansRint = 0.053
Absorption correction: multi-scan
sadabs
θmax = 25.1°, θmin = 1.6°
Tmin = 0.789, Tmax = 0.856h = 4346
17507 measured reflectionsk = 910
6366 independent reflectionsl = 3022
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.074 w = 1/[σ2(Fo2) + (0.0232P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
6366 reflectionsΔρmax = 1.00 e Å3
492 parametersΔρmin = 0.92 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*/UeqOcc. (<1)
Yb10.13568 (2)0.54182 (3)0.28109 (2)0.02122 (9)
Yb20.03415 (2)0.55663 (3)0.08921 (2)0.02319 (9)
S10.25400 (6)0.8856 (2)0.61052 (8)0.0314 (5)
N10.17019 (17)0.3112 (6)0.3486 (2)0.0265 (14)
N20.15559 (16)0.5702 (6)0.3905 (2)0.0241 (13)
N30.11110 (17)0.7817 (6)0.3014 (2)0.0276 (15)
O10.29624 (14)0.9044 (5)0.6677 (2)0.0340 (13)
O20.25352 (17)0.8332 (7)0.5570 (2)0.0565 (17)
O30.22934 (18)1.0210 (6)0.5988 (3)0.0667 (19)
O40.13842 (16)0.7150 (5)0.2181 (2)0.0384 (14)
O50.08974 (14)0.7012 (5)0.1148 (2)0.0321 (12)
O60.12980 (15)1.3781 (5)0.2097 (2)0.0362 (13)
O70.08168 (15)1.3807 (6)0.1050 (2)0.0384 (14)
O80.01253 (15)0.3178 (5)0.1090 (2)0.0375 (14)
O90.01044 (14)0.3640 (5)0.01067 (19)0.0277 (12)
O100.03145 (14)0.3754 (5)0.0634 (2)0.0350 (13)
O110.01484 (15)0.1916 (5)0.0969 (2)0.0346 (13)
O120.08102 (15)0.4360 (6)0.2824 (2)0.0382 (13)
O130.06128 (14)0.5603 (5)0.19553 (19)0.0274 (11)
C10.1779 (2)0.1848 (8)0.3263 (3)0.036 (2)
H10.17060.18610.28480.043*
C20.1962 (2)0.0544 (9)0.3621 (3)0.039 (2)
H20.20040.03100.34440.047*
C30.2083 (2)0.0497 (8)0.4237 (4)0.0365 (19)
H30.22060.03810.44850.044*
C40.2017 (2)0.1797 (7)0.4480 (3)0.0278 (17)
H40.20960.18020.48980.033*
C50.1831 (2)0.3105 (8)0.4099 (3)0.0252 (17)
C60.1762 (2)0.4555 (8)0.4339 (3)0.0263 (16)
C70.1916 (2)0.4731 (8)0.4977 (3)0.0285 (17)
H70.20490.39120.52570.034*
C80.1868 (2)0.6147 (8)0.5197 (3)0.0233 (16)
C90.1651 (2)0.7311 (8)0.4752 (3)0.0279 (17)
H90.16110.82640.48770.034*
C100.1493 (2)0.7035 (7)0.4117 (3)0.0234 (16)
C110.1239 (2)0.8210 (7)0.3616 (3)0.0223 (16)
C120.1128 (2)0.9621 (8)0.3741 (3)0.0288 (17)
H120.12100.98500.41520.035*
C130.0901 (2)1.0669 (8)0.3264 (3)0.0351 (19)
H130.08421.16370.33520.042*
C140.0760 (2)1.0268 (8)0.2654 (3)0.0345 (19)
H140.05951.09410.23180.041*
C150.0869 (2)0.8839 (8)0.2550 (3)0.0347 (19)
H150.07700.85700.21350.042*
C160.2035 (2)0.6272 (8)0.5889 (3)0.0250 (16)
C170.1900 (2)0.5171 (8)0.6117 (3)0.036 (2)
H170.17090.44380.58390.043*
C180.2039 (2)0.5126 (8)0.6748 (3)0.038 (2)
H180.19350.43860.68850.045*
C190.2329 (2)0.6165 (9)0.7173 (3)0.041 (2)
H190.24260.61310.75990.049*
C200.2473 (2)0.7265 (9)0.6955 (3)0.0335 (19)
H200.26750.79560.72440.040*
C210.2328 (2)0.7375 (7)0.6317 (3)0.0224 (16)
C220.1214 (2)0.7610 (7)0.1621 (3)0.0272 (17)
C230.1395 (2)0.8997 (7)0.1508 (3)0.0274 (17)
H23A0.13620.88960.11050.033*
H23B0.16870.90860.18430.033*
C240.1162 (2)1.0433 (8)0.1500 (3)0.0354 (19)
H24A0.08751.03640.11420.042*
H24B0.11711.04540.18860.042*
C250.1347 (2)1.1930 (7)0.1450 (3)0.0301 (18)
H25A0.16421.19520.17760.036*
H25B0.13031.19910.10390.036*
C260.1139 (2)1.3296 (7)0.1537 (3)0.0254 (17)
C270.0078 (2)0.2731 (8)0.0527 (3)0.0295 (18)
C280.0288 (2)0.1202 (8)0.0331 (3)0.036 (2)
H28A0.01170.04820.02890.043*
H28B0.05470.13070.00840.043*
C290.0377 (2)0.0516 (8)0.0794 (3)0.0343 (18)
H29A0.01270.05480.12220.041*
H29B0.05830.11460.07870.041*
C300.0532 (2)0.1153 (8)0.0629 (4)0.041 (2)
H30A0.06390.14430.08740.050*
H30B0.07600.11950.01830.050*
C310.0213 (2)0.2329 (8)0.0748 (3)0.0265 (17)
C320.0525 (2)0.4923 (9)0.2314 (3)0.0321 (19)
C330.0089 (3)0.4970 (16)0.2105 (4)0.105 (5)
H33A0.00880.46560.16640.126*
H33B0.00180.60250.21330.126*
C340.00000.3923 (19)0.25000.144 (10)
H34A0.02360.32680.27790.173*0.5
H34B0.02360.32680.22210.173*0.5
O140.14392 (19)0.1126 (7)0.5145 (3)0.072 (2)
O150.9035 (2)0.3985 (9)0.0016 (4)0.114 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Yb10.02104 (17)0.02171 (16)0.01488 (16)0.00128 (13)0.00673 (13)0.00071 (12)
Yb20.02392 (18)0.02331 (17)0.01495 (16)0.00012 (14)0.00678 (13)0.00041 (13)
S10.0240 (10)0.0338 (11)0.0241 (10)0.0050 (8)0.0065 (8)0.0038 (8)
N10.026 (3)0.026 (3)0.025 (3)0.003 (3)0.013 (3)0.000 (3)
N20.021 (3)0.020 (3)0.024 (3)0.001 (2)0.009 (3)0.004 (2)
N30.031 (4)0.023 (3)0.015 (3)0.002 (3)0.005 (3)0.000 (2)
O10.021 (3)0.044 (3)0.025 (3)0.011 (2)0.007 (2)0.002 (2)
O20.059 (4)0.084 (4)0.030 (3)0.044 (3)0.027 (3)0.022 (3)
O30.043 (4)0.039 (4)0.099 (5)0.007 (3)0.030 (4)0.027 (3)
O40.046 (3)0.036 (3)0.025 (3)0.004 (3)0.016 (3)0.005 (2)
O50.028 (3)0.035 (3)0.024 (3)0.001 (2)0.009 (2)0.004 (2)
O60.048 (3)0.032 (3)0.021 (3)0.002 (2)0.015 (2)0.006 (2)
O70.034 (3)0.037 (3)0.026 (3)0.008 (2)0.006 (2)0.002 (2)
O80.045 (3)0.040 (3)0.015 (3)0.011 (3)0.010 (2)0.002 (2)
O90.030 (3)0.029 (3)0.016 (2)0.003 (2)0.009 (2)0.004 (2)
O100.029 (3)0.028 (3)0.038 (3)0.001 (2)0.013 (2)0.006 (2)
O110.029 (3)0.029 (3)0.033 (3)0.003 (2)0.010 (2)0.001 (2)
O120.032 (3)0.048 (3)0.022 (3)0.004 (3)0.008 (2)0.010 (2)
O130.025 (3)0.037 (3)0.017 (2)0.004 (2)0.011 (2)0.005 (2)
C10.039 (5)0.037 (5)0.022 (4)0.013 (4)0.011 (4)0.000 (3)
C20.029 (4)0.041 (5)0.037 (5)0.010 (4)0.013 (4)0.008 (4)
C30.027 (4)0.026 (4)0.045 (5)0.011 (4)0.014 (4)0.012 (4)
C40.032 (4)0.027 (4)0.025 (4)0.002 (3)0.017 (3)0.010 (3)
C50.017 (4)0.031 (4)0.016 (4)0.001 (3)0.003 (3)0.001 (3)
C60.023 (4)0.032 (4)0.020 (4)0.012 (3)0.010 (3)0.005 (3)
C70.029 (4)0.031 (4)0.018 (4)0.002 (3)0.010 (3)0.007 (3)
C80.023 (4)0.030 (4)0.020 (4)0.007 (3)0.014 (3)0.005 (3)
C90.031 (4)0.026 (4)0.024 (4)0.007 (3)0.013 (3)0.005 (3)
C100.020 (4)0.023 (4)0.021 (4)0.008 (3)0.007 (3)0.004 (3)
C110.020 (4)0.025 (4)0.015 (4)0.004 (3)0.006 (3)0.001 (3)
C120.031 (4)0.033 (4)0.026 (4)0.001 (3)0.019 (3)0.004 (3)
C130.042 (5)0.019 (4)0.036 (5)0.004 (3)0.017 (4)0.000 (3)
C140.035 (5)0.033 (4)0.033 (4)0.014 (4)0.019 (4)0.007 (3)
C150.038 (5)0.034 (4)0.022 (4)0.005 (4)0.011 (4)0.001 (3)
C160.026 (4)0.030 (4)0.014 (4)0.001 (3)0.009 (3)0.001 (3)
C170.038 (5)0.040 (5)0.022 (4)0.015 (4)0.013 (4)0.001 (3)
C180.043 (5)0.041 (5)0.031 (4)0.003 (4)0.023 (4)0.016 (4)
C190.042 (5)0.058 (6)0.021 (4)0.004 (4)0.018 (4)0.007 (4)
C200.026 (4)0.049 (5)0.016 (4)0.002 (4)0.007 (3)0.004 (3)
C210.020 (4)0.026 (4)0.011 (3)0.000 (3)0.003 (3)0.001 (3)
C220.029 (4)0.019 (4)0.034 (5)0.009 (3)0.018 (4)0.001 (3)
C230.025 (4)0.027 (4)0.026 (4)0.000 (3)0.012 (3)0.001 (3)
C240.038 (5)0.031 (4)0.041 (5)0.005 (4)0.025 (4)0.003 (4)
C250.034 (5)0.022 (4)0.037 (5)0.002 (3)0.022 (4)0.003 (3)
C260.038 (5)0.014 (4)0.032 (4)0.004 (3)0.025 (4)0.004 (3)
C270.028 (4)0.025 (4)0.034 (5)0.003 (3)0.017 (4)0.005 (3)
C280.045 (5)0.035 (4)0.019 (4)0.005 (4)0.014 (4)0.009 (3)
C290.037 (5)0.031 (4)0.045 (5)0.007 (4)0.029 (4)0.004 (4)
C300.038 (5)0.031 (4)0.062 (6)0.000 (4)0.033 (4)0.008 (4)
C310.031 (5)0.030 (4)0.018 (4)0.000 (3)0.013 (3)0.004 (3)
C320.028 (4)0.050 (5)0.020 (4)0.005 (4)0.015 (4)0.011 (3)
C330.051 (7)0.226 (15)0.040 (6)0.019 (8)0.027 (5)0.038 (7)
C340.048 (11)0.074 (13)0.24 (2)0.0000.039 (14)0.000
O140.060 (4)0.094 (5)0.053 (4)0.009 (4)0.027 (3)0.028 (3)
O150.051 (5)0.095 (6)0.156 (7)0.004 (4)0.035 (5)0.015 (5)
Geometric parameters (Å, º) top
Yb1—O6i2.222 (4)C7—C81.407 (9)
Yb1—O42.252 (5)C7—H70.9300
Yb1—O1ii2.264 (4)C8—C91.391 (9)
Yb1—O122.362 (5)C8—C161.504 (8)
Yb1—N22.459 (5)C9—C101.393 (8)
Yb1—O132.469 (4)C9—H90.9300
Yb1—N32.471 (6)C10—C111.491 (8)
Yb1—N12.478 (5)C11—C121.395 (9)
Yb2—O7i2.265 (5)C12—C131.368 (9)
Yb2—O52.272 (5)C12—H120.9300
Yb2—O9iii2.275 (4)C13—C141.374 (9)
Yb2—O132.292 (4)C13—H130.9300
Yb2—O10iv2.352 (5)C14—C151.385 (9)
Yb2—O11iv2.355 (5)C14—H140.9300
Yb2—O82.399 (5)C15—H150.9300
Yb2—O92.426 (4)C16—C171.377 (9)
Yb2—C31iv2.705 (7)C16—C211.415 (8)
Yb2—Yb2iii3.8830 (9)C17—C181.380 (9)
S1—O21.437 (5)C17—H170.9300
S1—O31.441 (6)C18—C191.372 (10)
S1—O11.471 (4)C18—H180.9300
S1—C211.778 (7)C19—C201.382 (10)
N1—C51.349 (7)C19—H190.9300
N1—C11.349 (8)C20—C211.395 (8)
N2—C101.357 (8)C20—H200.9300
N2—C61.360 (8)C22—C231.508 (9)
N3—C151.346 (8)C23—C241.539 (9)
N3—C111.364 (7)C23—H23A0.9700
O1—Yb1ii2.264 (4)C23—H23B0.9700
O4—C221.253 (7)C24—C251.529 (9)
O5—C221.252 (8)C24—H24A0.9700
O6—C261.266 (7)C24—H24B0.9700
O6—Yb1iv2.222 (4)C25—C261.528 (9)
O7—C261.247 (8)C25—H25A0.9700
O7—Yb2iv2.265 (5)C25—H25B0.9700
O8—C271.249 (7)C27—C281.488 (9)
O9—C271.289 (8)C28—C291.540 (9)
O9—Yb2iii2.275 (4)C28—H28A0.9700
O10—C311.278 (8)C28—H28B0.9700
O10—Yb2i2.352 (5)C29—C301.531 (9)
O11—C311.248 (8)C29—H29A0.9700
O11—Yb2i2.355 (5)C29—H29B0.9700
O12—C321.238 (8)C30—C311.509 (10)
O13—C321.296 (8)C30—H30A0.9700
C1—C21.372 (9)C30—H30B0.9700
C1—H10.9300C31—Yb2i2.705 (7)
C2—C31.367 (9)C32—C331.483 (12)
C2—H20.9300C33—C341.541 (13)
C3—C41.382 (9)C33—H33A0.9700
C3—H30.9300C33—H33B0.9700
C4—C51.398 (8)C34—C33v1.541 (13)
C4—H40.9300C34—H34A0.9700
C5—C61.491 (9)C34—H34B0.9700
C6—C71.390 (8)
O6i—Yb1—O481.82 (18)N1—C5—C6116.3 (6)
O6i—Yb1—O1ii97.99 (18)C4—C5—C6122.7 (6)
O4—Yb1—O1ii75.58 (17)N2—C6—C7122.5 (6)
O6i—Yb1—O1295.71 (18)N2—C6—C5116.1 (6)
O4—Yb1—O12133.46 (17)C7—C6—C5121.3 (6)
O1ii—Yb1—O12149.57 (15)C6—C7—C8120.0 (6)
O6i—Yb1—N2145.15 (17)C6—C7—H7120.0
O4—Yb1—N2129.68 (17)C8—C7—H7120.0
O1ii—Yb1—N279.58 (17)C9—C8—C7117.5 (6)
O12—Yb1—N273.72 (17)C9—C8—C16124.5 (6)
O6i—Yb1—O1378.34 (16)C7—C8—C16117.9 (6)
O4—Yb1—O1380.76 (17)C8—C9—C10119.3 (6)
O1ii—Yb1—O13156.34 (16)C8—C9—H9120.3
O12—Yb1—O1353.59 (15)C10—C9—H9120.3
N2—Yb1—O13116.74 (17)N2—C10—C9123.5 (6)
O6i—Yb1—N3147.37 (17)N2—C10—C11115.0 (6)
O4—Yb1—N377.18 (18)C9—C10—C11121.5 (6)
O1ii—Yb1—N3100.59 (18)N3—C11—C12121.2 (6)
O12—Yb1—N381.40 (18)N3—C11—C10115.9 (6)
N2—Yb1—N365.31 (17)C12—C11—C10122.9 (6)
O13—Yb1—N373.88 (16)C13—C12—C11120.4 (6)
O6i—Yb1—N179.57 (17)C13—C12—H12119.8
O4—Yb1—N1143.62 (19)C11—C12—H12119.8
O1ii—Yb1—N176.40 (17)C12—C13—C14118.9 (7)
O12—Yb1—N179.56 (18)C12—C13—H13120.6
N2—Yb1—N165.98 (17)C14—C13—H13120.6
O13—Yb1—N1124.93 (17)C13—C14—C15118.6 (6)
N3—Yb1—N1130.88 (18)C13—C14—H14120.7
O7i—Yb2—O575.79 (18)C15—C14—H14120.7
O7i—Yb2—O9iii99.77 (17)N3—C15—C14123.9 (7)
O5—Yb2—O9iii82.30 (16)N3—C15—H15118.1
O7i—Yb2—O1391.22 (16)C14—C15—H15118.1
O5—Yb2—O1386.12 (16)C17—C16—C21118.7 (6)
O9iii—Yb2—O13161.53 (16)C17—C16—C8116.0 (6)
O7i—Yb2—O10iv152.19 (17)C21—C16—C8125.2 (6)
O5—Yb2—O10iv132.03 (17)C16—C17—C18121.9 (7)
O9iii—Yb2—O10iv86.00 (17)C16—C17—H17119.1
O13—Yb2—O10iv91.18 (16)C18—C17—H17119.1
O7i—Yb2—O11iv151.88 (18)C19—C18—C17120.3 (7)
O5—Yb2—O11iv76.79 (17)C19—C18—H18119.8
O9iii—Yb2—O11iv82.55 (16)C17—C18—H18119.8
O13—Yb2—O11iv80.82 (15)C18—C19—C20118.7 (7)
O10iv—Yb2—O11iv55.57 (16)C18—C19—H19120.6
O7i—Yb2—O875.02 (19)C20—C19—H19120.6
O5—Yb2—O8144.58 (16)C19—C20—C21122.3 (7)
O9iii—Yb2—O8122.17 (15)C19—C20—H20118.9
O13—Yb2—O874.92 (16)C21—C20—H20118.9
O10iv—Yb2—O878.88 (17)C20—C21—C16118.1 (6)
O11iv—Yb2—O8127.46 (19)C20—C21—S1117.3 (5)
O7i—Yb2—O979.60 (16)C16—C21—S1124.6 (5)
O5—Yb2—O9137.76 (16)O5—C22—O4124.3 (7)
O9iii—Yb2—O968.65 (18)O5—C22—C23117.5 (6)
O13—Yb2—O9128.45 (15)O4—C22—C23118.2 (6)
O10iv—Yb2—O977.26 (16)C22—C23—C24107.5 (6)
O11iv—Yb2—O9126.18 (16)C22—C23—H23A110.2
O8—Yb2—O953.63 (15)C24—C23—H23A110.2
O7i—Yb2—C31iv177.99 (18)C22—C23—H23B110.2
O5—Yb2—C31iv103.9 (2)C24—C23—H23B110.2
O9iii—Yb2—C31iv82.14 (18)H23A—C23—H23B108.5
O13—Yb2—C31iv86.77 (17)C25—C24—C23112.0 (6)
O10iv—Yb2—C31iv28.19 (17)C25—C24—H24A109.2
O11iv—Yb2—C31iv27.44 (17)C23—C24—H24A109.2
O8—Yb2—C31iv104.6 (2)C25—C24—H24B109.2
O9—Yb2—C31iv101.77 (18)C23—C24—H24B109.2
O7i—Yb2—Yb2iii89.24 (11)H24A—C24—H24B107.9
O5—Yb2—Yb2iii112.58 (11)C26—C25—C24108.7 (6)
O9iii—Yb2—Yb2iii35.58 (11)C26—C25—H25A110.0
O13—Yb2—Yb2iii160.77 (12)C24—C25—H25A110.0
O10iv—Yb2—Yb2iii79.71 (11)C26—C25—H25B110.0
O11iv—Yb2—Yb2iii107.03 (11)C24—C25—H25B110.0
O8—Yb2—Yb2iii86.64 (11)H25A—C25—H25B108.3
O9—Yb2—Yb2iii33.07 (10)O7—C26—O6125.4 (6)
C31iv—Yb2—Yb2iii92.71 (14)O7—C26—C25117.0 (6)
O2—S1—O3114.7 (4)O6—C26—C25117.5 (6)
O2—S1—O1112.2 (3)O8—C27—O9118.1 (6)
O3—S1—O1111.3 (3)O8—C27—C28122.1 (6)
O2—S1—C21108.3 (3)O9—C27—C28119.8 (6)
O3—S1—C21105.7 (3)C27—C28—C29114.3 (6)
O1—S1—C21103.7 (3)C27—C28—H28A108.7
C5—N1—C1117.8 (6)C29—C28—H28A108.7
C5—N1—Yb1120.6 (4)C27—C28—H28B108.7
C1—N1—Yb1121.6 (4)C29—C28—H28B108.7
C10—N2—C6117.0 (6)H28A—C28—H28B107.6
C10—N2—Yb1122.0 (4)C30—C29—C28112.4 (6)
C6—N2—Yb1120.9 (4)C30—C29—H29A109.1
C15—N3—C11117.0 (6)C28—C29—H29A109.1
C15—N3—Yb1122.0 (5)C30—C29—H29B109.1
C11—N3—Yb1120.8 (4)C28—C29—H29B109.1
S1—O1—Yb1ii153.3 (3)H29A—C29—H29B107.9
C22—O4—Yb1145.1 (5)C31—C30—C29115.2 (6)
C22—O5—Yb2140.4 (5)C31—C30—H30A108.5
C26—O6—Yb1iv153.8 (4)C29—C30—H30A108.5
C26—O7—Yb2iv133.0 (5)C31—C30—H30B108.5
C27—O8—Yb295.3 (4)C29—C30—H30B108.5
C27—O9—Yb2iii155.6 (4)H30A—C30—H30B107.5
C27—O9—Yb292.9 (4)O11—C31—O10120.6 (7)
Yb2iii—O9—Yb2111.35 (18)O11—C31—C30120.2 (6)
C31—O10—Yb2i91.5 (4)O10—C31—C30119.2 (7)
C31—O11—Yb2i92.1 (4)O11—C31—Yb2i60.4 (4)
C32—O12—Yb196.7 (4)O10—C31—Yb2i60.4 (4)
C32—O13—Yb2135.0 (4)C30—C31—Yb2i176.8 (5)
C32—O13—Yb190.2 (4)O12—C32—O13118.7 (7)
Yb2—O13—Yb1124.5 (2)O12—C32—C33123.9 (7)
N1—C1—C2122.9 (7)O13—C32—C33117.3 (7)
N1—C1—H1118.6C32—C33—C34113.6 (8)
C2—C1—H1118.6C32—C33—H33A108.8
C3—C2—C1120.2 (7)C34—C33—H33A108.8
C3—C2—H2119.9C32—C33—H33B108.8
C1—C2—H2119.9C34—C33—H33B108.8
C2—C3—C4117.8 (6)H33A—C33—H33B107.7
C2—C3—H3121.1C33—C34—C33v108.0 (15)
C4—C3—H3121.1C33—C34—H34A110.1
C3—C4—C5120.2 (7)C33v—C34—H34A110.1
C3—C4—H4119.9C33—C34—H34B110.1
C5—C4—H4119.9C33v—C34—H34B110.1
N1—C5—C4121.1 (6)H34A—C34—H34B108.4
O2—S1—O1—Yb1ii31.2 (8)C16—C17—C18—C191.9 (12)
O3—S1—O1—Yb1ii98.9 (7)C17—C18—C19—C200.9 (12)
C21—S1—O1—Yb1ii147.8 (6)C18—C19—C20—C211.5 (12)
C5—N1—C1—C23.5 (11)C19—C20—C21—C162.7 (11)
Yb1—N1—C1—C2178.6 (6)C19—C20—C21—S1179.6 (6)
N1—C1—C2—C31.5 (12)C17—C16—C21—C201.7 (10)
C1—C2—C3—C40.3 (11)C8—C16—C21—C20175.5 (6)
C2—C3—C4—C50.1 (11)C17—C16—C21—S1179.2 (6)
C1—N1—C5—C43.6 (10)C8—C16—C21—S12.0 (10)
Yb1—N1—C5—C4178.4 (5)O2—S1—C21—C20149.8 (5)
C1—N1—C5—C6176.5 (6)O3—S1—C21—C2086.8 (6)
Yb1—N1—C5—C61.5 (8)O1—S1—C21—C2030.4 (6)
C3—C4—C5—N11.9 (10)O2—S1—C21—C1627.7 (7)
C3—C4—C5—C6178.2 (7)O3—S1—C21—C1695.7 (6)
C10—N2—C6—C71.9 (10)O1—S1—C21—C16147.1 (6)
Yb1—N2—C6—C7173.5 (5)Yb2—O5—C22—O423.7 (11)
C10—N2—C6—C5179.5 (6)Yb2—O5—C22—C23155.0 (5)
Yb1—N2—C6—C54.2 (8)Yb1—O4—C22—O51.0 (13)
N1—C5—C6—N23.6 (9)Yb1—O4—C22—C23177.6 (5)
C4—C5—C6—N2176.3 (6)O5—C22—C23—C2485.0 (7)
N1—C5—C6—C7174.1 (6)O4—C22—C23—C2493.7 (7)
C4—C5—C6—C76.1 (10)C22—C23—C24—C25174.6 (6)
N2—C6—C7—C81.5 (10)C23—C24—C25—C26172.4 (6)
C5—C6—C7—C8176.1 (6)Yb2iv—O7—C26—O65.8 (11)
C6—C7—C8—C92.5 (10)Yb2iv—O7—C26—C25171.6 (4)
C6—C7—C8—C16179.3 (6)Yb1iv—O6—C26—O79.6 (16)
C7—C8—C9—C100.3 (10)Yb1iv—O6—C26—C25172.9 (7)
C16—C8—C9—C10176.8 (6)C24—C25—C26—O788.4 (8)
C6—N2—C10—C94.3 (10)C24—C25—C26—O689.2 (7)
Yb1—N2—C10—C9171.0 (5)Yb2—O8—C27—O92.7 (7)
C6—N2—C10—C11175.6 (6)Yb2—O8—C27—C28177.5 (6)
Yb1—N2—C10—C119.1 (8)Yb2iii—O9—C27—O8172.0 (8)
C8—C9—C10—N23.3 (10)Yb2—O9—C27—O82.7 (7)
C8—C9—C10—C11176.6 (6)Yb2iii—O9—C27—C287.8 (16)
C15—N3—C11—C121.0 (10)Yb2—O9—C27—C28177.5 (6)
Yb1—N3—C11—C12174.8 (5)O8—C27—C28—C2922.1 (10)
C15—N3—C11—C10177.8 (6)O9—C27—C28—C29157.7 (6)
Yb1—N3—C11—C106.4 (8)C27—C28—C29—C30171.3 (6)
N2—C10—C11—N31.6 (9)C28—C29—C30—C3170.5 (8)
C9—C10—C11—N3178.5 (6)Yb2i—O11—C31—O105.2 (6)
N2—C10—C11—C12177.2 (6)Yb2i—O11—C31—C30176.4 (6)
C9—C10—C11—C122.8 (10)Yb2i—O10—C31—O115.3 (6)
N3—C11—C12—C132.5 (11)Yb2i—O10—C31—C30176.4 (6)
C10—C11—C12—C13178.8 (6)C29—C30—C31—O110.3 (10)
C11—C12—C13—C144.3 (11)C29—C30—C31—O10178.6 (6)
C12—C13—C14—C152.7 (11)Yb1—O12—C32—O139.2 (7)
C11—N3—C15—C142.7 (11)Yb1—O12—C32—C33166.3 (9)
Yb1—N3—C15—C14173.0 (6)Yb2—O13—C32—O12134.8 (5)
C13—C14—C15—N30.9 (12)Yb1—O13—C32—O128.7 (7)
C9—C8—C16—C17122.3 (8)Yb2—O13—C32—C3349.4 (11)
C7—C8—C16—C1754.3 (9)Yb1—O13—C32—C33167.0 (8)
C9—C8—C16—C2160.5 (10)O12—C32—C33—C3413.7 (15)
C7—C8—C16—C21123.0 (8)O13—C32—C33—C34170.9 (9)
C21—C16—C17—C180.5 (11)C32—C33—C34—C33v110.7 (10)
C8—C16—C17—C18178.0 (7)
Symmetry codes: (i) x, y1, z; (ii) x+1/2, y+3/2, z+1; (iii) x, y+1, z; (iv) x, y+1, z; (v) x, y, z+1/2.
(4) top
Crystal data top
2(C29H18N3O7STb)·OF(000) = 1416
Mr = 1438.89Dx = 1.820 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.0175 (18) ÅCell parameters from 2199 reflections
b = 16.994 (3) Åθ = 2.3–21.3°
c = 14.608 (2) ŵ = 2.83 mm1
β = 106.227 (3)°T = 296 K
V = 2626.0 (7) Å3Block, yellow
Z = 20.13 × 0.10 × 0.09 mm
Data collection top
Bruker APEX-II CCD
diffractometer
3364 reflections with I > 2σ(I)
φ and ω scansRint = 0.061
Absorption correction: multi-scan
sadabs
θmax = 25.1°, θmin = 1.9°
Tmin = 0.634, Tmax = 0.768h = 1113
13056 measured reflectionsk = 2015
4647 independent reflectionsl = 1517
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.091 w = 1/[σ2(Fo2) + (0.0365P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
4647 reflectionsΔρmax = 1.40 e Å3
379 parametersΔρmin = 0.88 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*/UeqOcc. (<1)
Tb10.44863 (3)0.02537 (2)0.31007 (2)0.02328 (11)
S11.13235 (19)0.04248 (11)0.28158 (15)0.0451 (5)
N10.4208 (5)0.0436 (3)0.1503 (4)0.0378 (15)
N20.6466 (5)0.0188 (3)0.2718 (4)0.0342 (13)
N30.6500 (5)0.0922 (3)0.4003 (4)0.0363 (14)
O11.2655 (4)0.0469 (3)0.2817 (3)0.0421 (12)
O21.1206 (6)0.0057 (3)0.3678 (5)0.077 (2)
O31.0500 (6)0.0112 (3)0.1949 (5)0.082 (2)
O40.4821 (5)0.1402 (3)0.2233 (3)0.0493 (14)
O50.2882 (5)0.1064 (3)0.2161 (3)0.0489 (14)
O60.3963 (5)0.4208 (3)0.0677 (3)0.0442 (13)
O70.4776 (5)0.4251 (3)0.0911 (3)0.0422 (12)
C10.3108 (7)0.0401 (5)0.0807 (5)0.047 (2)
H10.24150.01690.09460.057*
C20.2959 (8)0.0688 (5)0.0091 (5)0.052 (2)
H20.21840.06480.05520.063*
C30.3968 (8)0.1035 (5)0.0303 (5)0.058 (2)
H30.38950.12270.09130.069*
C40.5102 (8)0.1096 (4)0.0409 (5)0.049 (2)
H40.57960.13400.02870.059*
C50.5188 (7)0.0790 (4)0.1297 (5)0.0380 (17)
C60.6417 (7)0.0762 (4)0.2057 (5)0.0372 (17)
C70.7439 (7)0.1233 (4)0.2077 (5)0.0388 (18)
H70.73730.16180.16130.047*
C80.8571 (7)0.1137 (4)0.2785 (5)0.0340 (16)
C90.8621 (7)0.0546 (4)0.3442 (5)0.0371 (17)
H90.93570.04660.39320.045*
C100.7591 (7)0.0080 (4)0.3372 (5)0.0361 (17)
C110.7629 (7)0.0638 (4)0.3963 (4)0.0343 (17)
C120.8775 (7)0.1033 (5)0.4358 (5)0.047 (2)
H120.95370.08170.43250.056*
C130.8741 (8)0.1751 (5)0.4799 (5)0.053 (2)
H130.94860.20230.50750.064*
C140.7589 (9)0.2058 (5)0.4824 (5)0.056 (2)
H140.75420.25430.51050.068*
C150.6504 (7)0.1624 (4)0.4418 (5)0.047 (2)
H150.57320.18350.44370.056*
C160.9649 (7)0.1679 (4)0.2811 (5)0.0348 (17)
C170.9407 (7)0.2486 (4)0.2805 (5)0.0399 (18)
H170.86070.26540.28130.048*
C181.0313 (8)0.3045 (4)0.2787 (5)0.047 (2)
H181.01250.35780.27900.056*
C191.1503 (8)0.2799 (4)0.2765 (5)0.048 (2)
H191.21110.31700.27320.057*
C201.1791 (7)0.2009 (4)0.2793 (5)0.0415 (18)
H201.25980.18500.27910.050*
C211.0869 (7)0.1436 (4)0.2823 (5)0.0339 (16)
C220.3652 (8)0.1477 (4)0.1875 (5)0.0360 (17)
C230.3133 (7)0.2048 (4)0.1081 (5)0.0339 (17)
C240.1994 (7)0.1899 (4)0.0416 (5)0.0351 (17)
H240.15280.14590.04880.042*
C250.1529 (7)0.2393 (4)0.0360 (5)0.0408 (18)
H250.07730.22780.08150.049*
C260.2220 (7)0.3067 (4)0.0443 (5)0.0352 (17)
H260.19140.34080.09540.042*
C270.3365 (6)0.3233 (4)0.0235 (4)0.0290 (15)
C280.3825 (7)0.2724 (4)0.1004 (5)0.0332 (16)
H280.45830.28320.14610.040*
C290.4080 (7)0.3963 (4)0.0151 (5)0.0329 (16)
O80.9993 (16)0.9567 (10)0.0054 (14)0.144 (8)0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Tb10.02827 (18)0.02210 (17)0.02125 (17)0.00072 (15)0.00988 (12)0.00018 (15)
S10.0390 (12)0.0349 (11)0.0649 (14)0.0026 (8)0.0203 (10)0.0052 (9)
N10.030 (4)0.051 (4)0.033 (3)0.002 (3)0.010 (3)0.006 (3)
N20.032 (3)0.047 (4)0.025 (3)0.004 (3)0.011 (3)0.001 (3)
N30.043 (4)0.036 (3)0.029 (3)0.004 (3)0.007 (3)0.007 (3)
O10.033 (3)0.035 (3)0.061 (3)0.006 (2)0.018 (2)0.001 (2)
O20.079 (5)0.062 (4)0.112 (5)0.025 (3)0.064 (4)0.047 (4)
O30.061 (4)0.060 (4)0.109 (5)0.000 (3)0.002 (4)0.042 (4)
O40.046 (4)0.046 (3)0.055 (3)0.003 (3)0.011 (3)0.021 (3)
O50.045 (3)0.048 (3)0.058 (3)0.003 (3)0.021 (3)0.024 (3)
O60.050 (3)0.052 (3)0.034 (3)0.004 (3)0.017 (2)0.009 (2)
O70.057 (4)0.031 (3)0.041 (3)0.009 (2)0.018 (3)0.004 (2)
C10.033 (5)0.071 (6)0.037 (4)0.004 (4)0.007 (4)0.013 (4)
C20.047 (5)0.069 (6)0.039 (5)0.002 (4)0.008 (4)0.011 (4)
C30.047 (6)0.084 (7)0.039 (5)0.008 (5)0.008 (4)0.028 (4)
C40.051 (6)0.057 (5)0.046 (5)0.000 (4)0.026 (4)0.018 (4)
C50.038 (5)0.043 (4)0.036 (4)0.001 (3)0.015 (4)0.007 (3)
C60.037 (5)0.044 (4)0.034 (4)0.006 (3)0.016 (3)0.006 (4)
C70.040 (5)0.038 (4)0.044 (4)0.002 (3)0.020 (4)0.009 (3)
C80.033 (4)0.033 (4)0.042 (4)0.003 (3)0.018 (3)0.002 (3)
C90.026 (4)0.048 (4)0.038 (4)0.000 (3)0.011 (3)0.004 (3)
C100.035 (4)0.049 (5)0.026 (4)0.009 (3)0.010 (3)0.005 (3)
C110.040 (5)0.035 (4)0.031 (4)0.001 (3)0.013 (3)0.004 (3)
C120.035 (5)0.066 (6)0.036 (4)0.006 (4)0.005 (4)0.007 (4)
C130.066 (7)0.059 (6)0.034 (4)0.022 (5)0.013 (4)0.013 (4)
C140.072 (7)0.046 (5)0.051 (5)0.017 (5)0.018 (5)0.014 (4)
C150.043 (5)0.047 (5)0.053 (5)0.003 (4)0.017 (4)0.006 (4)
C160.035 (5)0.034 (4)0.039 (4)0.001 (3)0.018 (3)0.001 (3)
C170.041 (5)0.043 (4)0.038 (4)0.007 (4)0.015 (4)0.000 (3)
C180.062 (6)0.030 (4)0.045 (5)0.005 (4)0.011 (4)0.000 (4)
C190.057 (6)0.039 (4)0.048 (5)0.012 (4)0.015 (4)0.001 (4)
C200.035 (5)0.045 (5)0.046 (5)0.000 (3)0.015 (4)0.006 (4)
C210.035 (4)0.031 (4)0.039 (4)0.000 (3)0.016 (3)0.000 (3)
C220.050 (5)0.027 (4)0.035 (4)0.006 (3)0.018 (4)0.002 (3)
C230.042 (5)0.030 (4)0.032 (4)0.001 (3)0.015 (3)0.007 (3)
C240.038 (5)0.026 (4)0.041 (4)0.007 (3)0.011 (4)0.000 (3)
C250.037 (5)0.046 (5)0.039 (4)0.008 (3)0.009 (4)0.000 (4)
C260.038 (5)0.030 (4)0.040 (4)0.002 (3)0.015 (4)0.006 (3)
C270.032 (4)0.025 (4)0.033 (4)0.002 (3)0.013 (3)0.002 (3)
C280.037 (4)0.034 (4)0.030 (4)0.003 (3)0.013 (3)0.001 (3)
C290.040 (5)0.026 (4)0.038 (4)0.005 (3)0.019 (4)0.001 (3)
O80.090 (13)0.17 (2)0.147 (15)0.065 (14)0.008 (10)0.020 (16)
Geometric parameters (Å, º) top
Tb1—O6i2.220 (4)C4—C51.377 (9)
Tb1—O7ii2.234 (5)C5—C61.492 (10)
Tb1—O1iii2.299 (4)C6—C71.375 (9)
Tb1—O52.355 (5)C7—C81.389 (9)
Tb1—O42.411 (5)C8—C91.379 (9)
Tb1—N32.512 (5)C8—C161.494 (9)
Tb1—N22.513 (5)C9—C101.365 (9)
Tb1—N12.553 (5)C10—C111.488 (9)
S1—O31.438 (6)C11—C121.403 (9)
S1—O21.444 (6)C12—C131.385 (10)
S1—O11.468 (5)C13—C141.382 (11)
S1—C211.791 (7)C14—C151.388 (10)
N1—C51.341 (8)C16—C171.397 (9)
N1—C11.348 (8)C16—C211.402 (9)
N2—C101.350 (8)C17—C181.382 (10)
N2—C61.363 (8)C18—C191.385 (10)
N3—C151.339 (8)C19—C201.378 (10)
N3—C111.351 (8)C20—C211.416 (9)
O1—Tb1iv2.299 (4)C22—C231.498 (9)
O4—C221.254 (8)C23—C241.380 (9)
O5—C221.258 (8)C23—C281.399 (9)
O6—C291.251 (7)C24—C251.388 (9)
O6—Tb1v2.220 (4)C25—C261.399 (9)
O7—C291.259 (7)C26—C271.398 (9)
O7—Tb1vi2.235 (5)C27—C281.396 (8)
C1—C21.367 (9)C27—C291.494 (9)
C2—C31.368 (10)O8—O8vii1.48 (3)
C3—C41.388 (10)
O6i—Tb1—O7ii85.63 (17)C2—C3—C4118.7 (7)
O6i—Tb1—O1iii87.31 (17)C5—C4—C3119.3 (7)
O7ii—Tb1—O1iii81.46 (17)N1—C5—C4122.2 (7)
O6i—Tb1—O584.64 (17)N1—C5—C6116.1 (6)
O7ii—Tb1—O5154.22 (17)C4—C5—C6121.5 (6)
O1iii—Tb1—O574.29 (17)N2—C6—C7122.1 (6)
O6i—Tb1—O4101.63 (18)N2—C6—C5113.4 (6)
O7ii—Tb1—O4151.10 (18)C7—C6—C5124.4 (6)
O1iii—Tb1—O4126.39 (17)C6—C7—C8120.5 (7)
O5—Tb1—O454.60 (17)C9—C8—C7117.2 (6)
O6i—Tb1—N377.39 (18)C9—C8—C16123.6 (6)
O7ii—Tb1—N384.10 (18)C7—C8—C16119.2 (6)
O1iii—Tb1—N3159.69 (17)C10—C9—C8120.0 (7)
O5—Tb1—N3116.77 (18)N2—C10—C9123.6 (6)
O4—Tb1—N370.59 (17)N2—C10—C11113.2 (6)
O6i—Tb1—N2137.59 (17)C9—C10—C11123.0 (6)
O7ii—Tb1—N274.61 (17)N3—C11—C12123.0 (7)
O1iii—Tb1—N2124.96 (17)N3—C11—C10116.1 (6)
O5—Tb1—N2126.98 (17)C12—C11—C10120.5 (7)
O4—Tb1—N281.65 (18)C13—C12—C11118.3 (7)
N3—Tb1—N263.75 (18)C14—C13—C12119.3 (8)
O6i—Tb1—N1158.82 (18)C13—C14—C15118.5 (8)
O7ii—Tb1—N199.77 (17)N3—C15—C14124.0 (8)
O1iii—Tb1—N173.42 (17)C17—C16—C21117.9 (6)
O5—Tb1—N181.76 (18)C17—C16—C8117.1 (6)
O4—Tb1—N183.56 (17)C21—C16—C8124.9 (6)
N3—Tb1—N1123.36 (18)C18—C17—C16122.5 (7)
N2—Tb1—N163.21 (18)C17—C18—C19119.1 (7)
O3—S1—O2114.8 (4)C20—C19—C18120.3 (7)
O3—S1—O1113.9 (3)C19—C20—C21120.6 (7)
O2—S1—O1110.7 (3)C16—C21—C20119.5 (6)
O3—S1—C21104.6 (3)C16—C21—S1123.4 (5)
O2—S1—C21108.5 (3)C20—C21—S1117.1 (5)
O1—S1—C21103.4 (3)O4—C22—O5120.9 (6)
C5—N1—C1117.5 (6)O4—C22—C23120.9 (6)
C5—N1—Tb1120.8 (4)O5—C22—C23118.2 (7)
C1—N1—Tb1121.4 (5)C24—C23—C28120.2 (6)
C10—N2—C6116.5 (6)C24—C23—C22120.1 (6)
C10—N2—Tb1118.9 (4)C28—C23—C22119.7 (6)
C6—N2—Tb1120.4 (4)C23—C24—C25121.3 (6)
C15—N3—C11116.8 (6)C24—C25—C26118.7 (7)
C15—N3—Tb1122.1 (5)C27—C26—C25120.6 (6)
C11—N3—Tb1120.3 (4)C28—C27—C26119.9 (6)
S1—O1—Tb1iv143.0 (3)C28—C27—C29120.0 (6)
C22—O4—Tb190.6 (4)C26—C27—C29120.1 (6)
C22—O5—Tb193.1 (5)C27—C28—C23119.3 (6)
C29—O6—Tb1v159.2 (5)O6—C29—O7126.6 (6)
C29—O7—Tb1vi152.6 (4)O6—C29—C27116.2 (6)
N1—C1—C2123.3 (7)O7—C29—C27117.1 (6)
C1—C2—C3119.0 (7)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y1/2, z+1/2; (iii) x1, y, z; (iv) x+1, y, z; (v) x, y+1/2, z1/2; (vi) x+1, y+1/2, z+1/2; (vii) x+2, y+2, z.
(5) top
Crystal data top
2(C29H18N3O7SYb)·OF(000) = 1436
Mr = 1467.13Dx = 1.859 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.0067 (12) ÅCell parameters from 3822 reflections
b = 16.9842 (19) Åθ = 2.4–26.2°
c = 14.5971 (16) ŵ = 3.71 mm1
β = 106.203 (2)°T = 296 K
V = 2620.4 (5) Å3Block, yellow
Z = 20.14 × 0.13 × 0.10 mm
Data collection top
Bruker APEX-II CCD
diffractometer
3881 reflections with I > 2σ(I)
φ and ω scansRint = 0.040
Absorption correction: multi-scan
sadabs
θmax = 25.1°, θmin = 2.3°
Tmin = 0.567, Tmax = 0.678h = 1311
12880 measured reflectionsk = 1420
4638 independent reflectionsl = 1717
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.073 w = 1/[σ2(Fo2) + (0.0326P)2 + 1.1125P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.002
4638 reflectionsΔρmax = 0.62 e Å3
379 parametersΔρmin = 0.97 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*/UeqOcc. (<1)
Yb10.55123 (2)1.02537 (2)0.68995 (2)0.02117 (8)
S10.13273 (12)0.95704 (7)0.71853 (11)0.0338 (3)
N10.3491 (4)1.0927 (2)0.5989 (3)0.0267 (9)
N20.3532 (4)0.9805 (2)0.7280 (3)0.0228 (9)
N30.5793 (4)0.9567 (2)0.8498 (3)0.0273 (9)
O10.2654 (3)0.9526 (2)0.7188 (2)0.0313 (8)
O20.0519 (4)0.9883 (3)0.8044 (3)0.0648 (15)
O30.1206 (4)0.9936 (2)0.6326 (4)0.0623 (14)
O40.4776 (3)0.92488 (19)0.5905 (2)0.0301 (8)
O50.3970 (3)0.9206 (2)0.4327 (2)0.0313 (8)
O60.4814 (3)0.6398 (2)0.7230 (2)0.0386 (9)
O70.2882 (3)0.6064 (2)0.7157 (2)0.0363 (9)
C10.3488 (5)1.1626 (3)0.5576 (4)0.0367 (13)
H10.42601.18380.55590.044*
C20.2413 (5)1.2055 (3)0.5176 (4)0.0418 (14)
H20.24571.25390.48890.050*
C30.1271 (5)1.1748 (4)0.5209 (4)0.0415 (14)
H30.05231.20210.49410.050*
C40.1248 (5)1.1037 (3)0.5642 (3)0.0335 (12)
H40.04831.08230.56720.040*
C50.2365 (5)1.0637 (3)0.6035 (3)0.0267 (11)
C60.2427 (5)0.9928 (3)0.6629 (3)0.0258 (11)
C70.1369 (4)0.9451 (3)0.6553 (3)0.0270 (11)
H70.06340.95280.60590.032*
C80.1425 (4)0.8862 (3)0.7221 (3)0.0259 (11)
C90.2562 (4)0.8763 (3)0.7924 (3)0.0313 (12)
H90.26380.83750.83860.038*
C100.3587 (4)0.9246 (3)0.7937 (3)0.0254 (11)
C110.4805 (4)0.9217 (3)0.8700 (3)0.0263 (11)
C120.4903 (5)0.8896 (3)0.9594 (4)0.0399 (14)
H120.42150.86380.97090.048*
C130.6021 (5)0.8960 (4)1.0309 (4)0.0474 (16)
H130.60870.87691.09180.057*
C140.7036 (5)0.9312 (4)1.0102 (4)0.0440 (15)
H140.78070.93591.05660.053*
C150.6886 (5)0.9597 (3)0.9182 (4)0.0353 (13)
H150.75830.98200.90390.042*
C160.0347 (4)0.8316 (3)0.7187 (3)0.0253 (11)
C170.0590 (5)0.7513 (3)0.7197 (4)0.0329 (12)
H170.13920.73450.71910.039*
C180.0313 (5)0.6958 (3)0.7214 (4)0.0387 (13)
H180.01230.64250.72120.046*
C190.1495 (5)0.7196 (3)0.7234 (4)0.0359 (13)
H190.21050.68250.72610.043*
C200.1777 (4)0.7993 (3)0.7215 (4)0.0317 (12)
H200.25800.81520.72270.038*
C210.0878 (4)0.8557 (3)0.7176 (3)0.0240 (10)
C220.4088 (4)0.8961 (3)0.5156 (3)0.0212 (10)
C230.3348 (4)0.8227 (3)0.5240 (3)0.0200 (10)
C240.2222 (4)0.8056 (3)0.4556 (3)0.0269 (11)
H240.19250.83880.40340.032*
C250.1546 (4)0.7396 (3)0.4653 (3)0.0284 (11)
H250.07860.72860.41990.034*
C260.1989 (4)0.6896 (3)0.5418 (3)0.0270 (11)
H260.15170.64580.54900.032*
C270.3143 (4)0.7050 (3)0.6081 (3)0.0222 (10)
C280.3812 (4)0.7723 (3)0.6001 (3)0.0206 (10)
H280.45690.78360.64570.025*
C290.3639 (5)0.6480 (3)0.6878 (3)0.0252 (11)
O80.9993 (13)0.9560 (8)0.9956 (10)0.131 (6)0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Yb10.02298 (13)0.02200 (12)0.01985 (12)0.00085 (9)0.00817 (9)0.00006 (9)
S10.0248 (7)0.0264 (7)0.0530 (8)0.0026 (5)0.0152 (6)0.0048 (6)
N10.031 (2)0.024 (2)0.025 (2)0.0006 (18)0.0086 (19)0.0045 (18)
N20.022 (2)0.029 (2)0.0176 (19)0.0010 (18)0.0062 (17)0.0016 (18)
N30.021 (2)0.034 (2)0.028 (2)0.0019 (17)0.0078 (18)0.0041 (19)
O10.0234 (18)0.0305 (19)0.044 (2)0.0046 (14)0.0164 (16)0.0017 (17)
O20.042 (3)0.045 (3)0.095 (4)0.003 (2)0.003 (3)0.039 (3)
O30.064 (3)0.043 (2)0.101 (4)0.020 (2)0.059 (3)0.035 (3)
O40.038 (2)0.0212 (18)0.0312 (18)0.0086 (16)0.0101 (16)0.0053 (16)
O50.037 (2)0.0303 (19)0.0308 (18)0.0039 (16)0.0162 (16)0.0095 (16)
O60.028 (2)0.042 (2)0.043 (2)0.0024 (17)0.0054 (17)0.0187 (18)
O70.032 (2)0.035 (2)0.046 (2)0.0016 (17)0.0185 (18)0.0209 (18)
C10.037 (3)0.040 (3)0.037 (3)0.000 (3)0.016 (3)0.007 (3)
C20.053 (4)0.035 (3)0.036 (3)0.015 (3)0.011 (3)0.014 (3)
C30.037 (3)0.053 (4)0.033 (3)0.020 (3)0.008 (3)0.008 (3)
C40.026 (3)0.045 (3)0.028 (3)0.008 (2)0.005 (2)0.004 (3)
C50.029 (3)0.033 (3)0.018 (2)0.004 (2)0.008 (2)0.001 (2)
C60.028 (3)0.033 (3)0.021 (2)0.004 (2)0.014 (2)0.000 (2)
C70.016 (2)0.039 (3)0.025 (2)0.002 (2)0.005 (2)0.002 (2)
C80.020 (2)0.028 (3)0.035 (3)0.003 (2)0.018 (2)0.001 (2)
C90.024 (3)0.040 (3)0.034 (3)0.001 (2)0.013 (2)0.009 (2)
C100.022 (3)0.038 (3)0.020 (2)0.004 (2)0.013 (2)0.003 (2)
C110.024 (3)0.031 (3)0.026 (2)0.005 (2)0.010 (2)0.009 (2)
C120.031 (3)0.055 (4)0.039 (3)0.007 (3)0.018 (3)0.022 (3)
C130.040 (3)0.075 (5)0.028 (3)0.014 (3)0.011 (3)0.024 (3)
C140.034 (3)0.066 (4)0.026 (3)0.007 (3)0.002 (2)0.007 (3)
C150.023 (3)0.050 (4)0.031 (3)0.001 (2)0.004 (2)0.010 (3)
C160.024 (3)0.031 (3)0.021 (2)0.000 (2)0.007 (2)0.005 (2)
C170.030 (3)0.039 (3)0.032 (3)0.006 (2)0.014 (2)0.002 (2)
C180.046 (3)0.027 (3)0.037 (3)0.006 (3)0.002 (3)0.001 (2)
C190.035 (3)0.031 (3)0.037 (3)0.008 (2)0.003 (2)0.002 (3)
C200.018 (3)0.038 (3)0.040 (3)0.003 (2)0.010 (2)0.000 (3)
C210.023 (3)0.024 (3)0.027 (2)0.002 (2)0.011 (2)0.000 (2)
C220.022 (2)0.019 (2)0.025 (3)0.0001 (19)0.011 (2)0.002 (2)
C230.022 (2)0.021 (2)0.019 (2)0.0023 (19)0.010 (2)0.003 (2)
C240.031 (3)0.026 (3)0.023 (2)0.002 (2)0.007 (2)0.005 (2)
C250.021 (3)0.032 (3)0.030 (3)0.005 (2)0.004 (2)0.003 (2)
C260.030 (3)0.024 (3)0.029 (3)0.007 (2)0.010 (2)0.001 (2)
C270.028 (3)0.021 (2)0.021 (2)0.004 (2)0.012 (2)0.004 (2)
C280.021 (2)0.024 (3)0.017 (2)0.001 (2)0.0059 (19)0.000 (2)
C290.032 (3)0.019 (2)0.023 (2)0.001 (2)0.006 (2)0.001 (2)
O80.106 (10)0.145 (13)0.120 (11)0.045 (11)0.006 (9)0.034 (11)
Geometric parameters (Å, º) top
Yb1—O5i2.222 (3)C7—H70.9300
Yb1—O42.241 (3)C8—C91.389 (6)
Yb1—O1ii2.303 (3)C8—C161.495 (6)
Yb1—O7iii2.357 (3)C9—C101.390 (6)
Yb1—O6iii2.402 (3)C9—H90.9300
Yb1—N22.513 (4)C10—C111.486 (6)
Yb1—N12.524 (4)C11—C121.391 (6)
Yb1—N32.549 (4)C12—C131.378 (8)
Yb1—C29iii2.732 (5)C12—H120.9300
S1—O21.422 (4)C13—C141.373 (8)
S1—O31.439 (5)C13—H130.9300
S1—O11.463 (3)C14—C151.393 (7)
S1—C211.792 (5)C14—H140.9300
N1—C11.332 (6)C15—H150.9300
N1—C51.352 (6)C16—C171.389 (7)
N2—C61.335 (6)C16—C211.405 (6)
N2—C101.339 (6)C17—C181.375 (7)
N3—C151.333 (6)C17—H170.9300
N3—C111.342 (6)C18—C191.370 (7)
O1—Yb1iv2.303 (3)C18—H180.9300
O4—C221.244 (5)C19—C201.387 (7)
O5—C221.252 (5)C19—H190.9300
O5—Yb1i2.222 (3)C20—C211.390 (6)
O6—C291.258 (6)C20—H200.9300
O6—Yb1v2.402 (3)C22—C231.512 (6)
O7—C291.245 (5)C23—C281.382 (6)
O7—Yb1v2.357 (3)C23—C241.389 (6)
C1—C21.372 (7)C24—C251.374 (7)
C1—H10.9300C24—H240.9300
C2—C31.374 (8)C25—C261.380 (7)
C2—H20.9300C25—H250.9300
C3—C41.367 (7)C26—C271.390 (6)
C3—H30.9300C26—H260.9300
C4—C51.381 (6)C27—C281.382 (6)
C4—H40.9300C27—C291.495 (6)
C5—C61.473 (7)C28—H280.9300
C6—C71.398 (7)C29—Yb1v2.732 (5)
C7—C81.387 (6)O8—O8vi1.50 (3)
O5i—Yb1—O485.43 (12)C7—C6—C5121.8 (4)
O5i—Yb1—O1ii87.70 (12)C8—C7—C6119.3 (4)
O4—Yb1—O1ii81.36 (12)C8—C7—H7120.3
O5i—Yb1—O7iii84.86 (12)C6—C7—H7120.3
O4—Yb1—O7iii154.15 (12)C7—C8—C9117.4 (4)
O1ii—Yb1—O7iii74.37 (12)C7—C8—C16123.0 (4)
O5i—Yb1—O6iii101.63 (12)C9—C8—C16119.5 (4)
O4—Yb1—O6iii151.43 (12)C8—C9—C10119.9 (5)
O1ii—Yb1—O6iii126.15 (12)C8—C9—H9120.0
O7iii—Yb1—O6iii54.35 (11)C10—C9—H9120.0
O5i—Yb1—N2137.41 (12)N2—C10—C9122.3 (4)
O4—Yb1—N274.49 (12)N2—C10—C11114.3 (4)
O1ii—Yb1—N2124.52 (12)C9—C10—C11123.4 (4)
O7iii—Yb1—N2127.11 (12)N3—C11—C12121.6 (4)
O6iii—Yb1—N282.07 (12)N3—C11—C10116.0 (4)
O5i—Yb1—N177.04 (12)C12—C11—C10122.3 (4)
O4—Yb1—N184.12 (13)C13—C12—C11119.9 (5)
O1ii—Yb1—N1159.70 (12)C13—C12—H12120.0
O7iii—Yb1—N1116.76 (13)C11—C12—H12120.0
O6iii—Yb1—N170.87 (12)C14—C13—C12118.5 (5)
N2—Yb1—N164.04 (12)C14—C13—H13120.8
O5i—Yb1—N3158.93 (13)C12—C13—H13120.8
O4—Yb1—N3100.02 (12)C13—C14—C15118.6 (5)
O1ii—Yb1—N373.20 (12)C13—C14—H14120.7
O7iii—Yb1—N381.54 (13)C15—C14—H14120.7
O6iii—Yb1—N383.35 (13)N3—C15—C14123.2 (5)
N2—Yb1—N363.27 (12)N3—C15—H15118.4
N1—Yb1—N3123.57 (12)C14—C15—H15118.4
O5i—Yb1—C29iii95.38 (13)C17—C16—C21117.8 (4)
O4—Yb1—C29iii178.74 (13)C17—C16—C8117.4 (4)
O1ii—Yb1—C29iii99.63 (14)C21—C16—C8124.8 (4)
O7iii—Yb1—C29iii27.05 (12)C18—C17—C16122.4 (5)
O6iii—Yb1—C29iii27.43 (12)C18—C17—H17118.8
N2—Yb1—C29iii104.27 (13)C16—C17—H17118.8
N1—Yb1—C29iii95.12 (13)C19—C18—C17119.6 (5)
N3—Yb1—C29iii79.56 (13)C19—C18—H18120.2
O2—S1—O3114.9 (3)C17—C18—H18120.2
O2—S1—O1113.4 (2)C18—C19—C20119.7 (5)
O3—S1—O1111.1 (2)C18—C19—H19120.2
O2—S1—C21105.0 (2)C20—C19—H19120.2
O3—S1—C21108.3 (2)C19—C20—C21121.1 (5)
O1—S1—C21103.2 (2)C19—C20—H20119.5
C1—N1—C5117.4 (4)C21—C20—H20119.5
C1—N1—Yb1122.2 (3)C20—C21—C16119.4 (4)
C5—N1—Yb1119.7 (3)C20—C21—S1117.4 (4)
C6—N2—C10118.1 (4)C16—C21—S1123.1 (4)
C6—N2—Yb1118.0 (3)O4—C22—O5126.3 (4)
C10—N2—Yb1120.3 (3)O4—C22—C23117.5 (4)
C15—N3—C11118.0 (4)O5—C22—C23116.1 (4)
C15—N3—Yb1121.4 (3)C28—C23—C24120.3 (4)
C11—N3—Yb1120.3 (3)C28—C23—C22119.3 (4)
S1—O1—Yb1iv142.8 (2)C24—C23—C22120.4 (4)
C22—O4—Yb1153.0 (3)C25—C24—C23119.8 (4)
C22—O5—Yb1i159.2 (3)C25—C24—H24120.1
C29—O6—Yb1v91.0 (3)C23—C24—H24120.1
C29—O7—Yb1v93.5 (3)C24—C25—C26120.4 (4)
N1—C1—C2124.0 (5)C24—C25—H25119.8
N1—C1—H1118.0C26—C25—H25119.8
C2—C1—H1118.0C25—C26—C27119.7 (4)
C1—C2—C3118.2 (5)C25—C26—H26120.1
C1—C2—H2120.9C27—C26—H26120.1
C3—C2—H2120.9C28—C27—C26120.1 (4)
C4—C3—C2119.0 (5)C28—C27—C29120.9 (4)
C4—C3—H3120.5C26—C27—C29119.0 (4)
C2—C3—H3120.5C27—C28—C23119.6 (4)
C3—C4—C5119.9 (5)C27—C28—H28120.2
C3—C4—H4120.0C23—C28—H28120.2
C5—C4—H4120.0O7—C29—O6120.6 (4)
N1—C5—C4121.5 (5)O7—C29—C27119.3 (4)
N1—C5—C6115.7 (4)O6—C29—C27120.0 (4)
C4—C5—C6122.4 (5)O7—C29—Yb1v59.5 (2)
N2—C6—C7122.6 (4)O6—C29—Yb1v61.5 (2)
N2—C6—C5115.5 (4)C27—C29—Yb1v170.5 (3)
O2—S1—O1—Yb1iv84.4 (4)C13—C14—C15—N32.1 (9)
O3—S1—O1—Yb1iv46.7 (4)C7—C8—C16—C17125.9 (5)
C21—S1—O1—Yb1iv162.6 (3)C9—C8—C16—C1751.3 (6)
C5—N1—C1—C21.9 (8)C7—C8—C16—C2156.2 (7)
Yb1—N1—C1—C2171.8 (4)C9—C8—C16—C21126.6 (5)
N1—C1—C2—C30.6 (8)C21—C16—C17—C181.2 (7)
C1—C2—C3—C40.4 (8)C8—C16—C17—C18176.8 (5)
C2—C3—C4—C50.2 (8)C16—C17—C18—C190.8 (8)
C1—N1—C5—C42.1 (7)C17—C18—C19—C201.5 (8)
Yb1—N1—C5—C4172.3 (3)C18—C19—C20—C210.1 (8)
C1—N1—C5—C6170.5 (4)C19—C20—C21—C162.0 (7)
Yb1—N1—C5—C60.3 (5)C19—C20—C21—S1178.4 (4)
C3—C4—C5—N11.1 (7)C17—C16—C21—C202.6 (7)
C3—C4—C5—C6171.0 (5)C8—C16—C21—C20175.3 (4)
C10—N2—C6—C76.3 (7)C17—C16—C21—S1178.8 (4)
Yb1—N2—C6—C7152.6 (4)C8—C16—C21—S10.9 (7)
C10—N2—C6—C5169.6 (4)O2—S1—C21—C20116.3 (4)
Yb1—N2—C6—C531.5 (5)O3—S1—C21—C20120.5 (4)
N1—C5—C6—N220.8 (6)O1—S1—C21—C202.7 (4)
C4—C5—C6—N2151.7 (5)O2—S1—C21—C1659.9 (5)
N1—C5—C6—C7163.2 (4)O3—S1—C21—C1663.2 (5)
C4—C5—C6—C724.2 (7)O1—S1—C21—C16178.9 (4)
N2—C6—C7—C85.2 (7)Yb1—O4—C22—O550.3 (9)
C5—C6—C7—C8170.5 (4)Yb1—O4—C22—C23131.8 (5)
C6—C7—C8—C91.8 (7)Yb1i—O5—C22—O433.4 (12)
C6—C7—C8—C16179.1 (4)Yb1i—O5—C22—C23144.5 (7)
C7—C8—C9—C100.1 (7)O4—C22—C23—C2827.4 (6)
C16—C8—C9—C10177.2 (4)O5—C22—C23—C28150.7 (4)
C6—N2—C10—C94.2 (7)O4—C22—C23—C24153.3 (4)
Yb1—N2—C10—C9154.2 (4)O5—C22—C23—C2428.6 (6)
C6—N2—C10—C11172.8 (4)C28—C23—C24—C252.1 (7)
Yb1—N2—C10—C1128.9 (5)C22—C23—C24—C25178.7 (4)
C8—C9—C10—N21.0 (7)C23—C24—C25—C260.9 (7)
C8—C9—C10—C11175.6 (4)C24—C25—C26—C271.8 (7)
C15—N3—C11—C120.1 (7)C25—C26—C27—C283.4 (7)
Yb1—N3—C11—C12174.5 (4)C25—C26—C27—C29176.9 (4)
C15—N3—C11—C10176.0 (4)C26—C27—C28—C232.3 (7)
Yb1—N3—C11—C101.3 (6)C29—C27—C28—C23178.1 (4)
N2—C10—C11—N319.2 (6)C24—C23—C28—C270.5 (7)
C9—C10—C11—N3163.8 (5)C22—C23—C28—C27179.7 (4)
N2—C10—C11—C12156.6 (5)Yb1v—O7—C29—O67.7 (5)
C9—C10—C11—C1220.3 (8)Yb1v—O7—C29—C27169.1 (4)
N3—C11—C12—C132.6 (8)Yb1v—O6—C29—O77.5 (5)
C10—C11—C12—C13173.0 (5)Yb1v—O6—C29—C27169.2 (4)
C11—C12—C13—C143.0 (9)C28—C27—C29—O7152.9 (4)
C12—C13—C14—C150.8 (9)C26—C27—C29—O726.7 (6)
C11—N3—C15—C142.5 (8)C28—C27—C29—O630.3 (7)
Yb1—N3—C15—C14172.1 (4)C26—C27—C29—O6150.1 (5)
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y, z; (iii) x+1, y+1/2, z+3/2; (iv) x1, y, z; (v) x+1, y1/2, z+3/2; (vi) x+2, y+2, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···O80.932.653.289 (15)126
C7—H7···O30.932.272.880 (6)122
C1—H1···O5i0.932.603.103 (6)114
Symmetry code: (i) x+1, y+2, z+1.
(6) top
Crystal data top
C29H18EuN3O7SF(000) = 1392
Mr = 704.48Dx = 1.845 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 9.1596 (9) ÅCell parameters from 5032 reflections
b = 13.4942 (13) Åθ = 2.3–26.3°
c = 20.727 (2) ŵ = 2.61 mm1
β = 98.039 (2)°T = 296 K
V = 2536.7 (4) Å3Block, yellow
Z = 40.24 × 0.18 × 0.12 mm
Data collection top
Bruker APEX-II CCD
diffractometer
3916 reflections with I > 2σ(I)
φ and ω scansRint = 0.027
Absorption correction: multi-scan
sadabs
θmax = 25.1°, θmin = 1.8°
Tmin = 0.574, Tmax = 0.733h = 1010
12565 measured reflectionsk = 1612
4478 independent reflectionsl = 2424
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.023H-atom parameters constrained
wR(F2) = 0.052 w = 1/[σ2(Fo2) + (0.0211P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max < 0.001
4478 reflectionsΔρmax = 0.37 e Å3
370 parametersΔρmin = 0.35 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
Eu10.27732 (2)0.08032 (2)0.05431 (2)0.02036 (6)
S10.28268 (10)0.50603 (7)0.27766 (4)0.0359 (2)
N10.5151 (3)0.10483 (18)0.13425 (12)0.0245 (6)
N20.3324 (3)0.25673 (18)0.09190 (11)0.0221 (5)
N30.1461 (3)0.21966 (18)0.01794 (12)0.0271 (6)
O10.2547 (3)0.56975 (17)0.33238 (11)0.0401 (6)
O20.1486 (3)0.4713 (2)0.23932 (12)0.0619 (8)
O30.3902 (3)0.43098 (18)0.29829 (13)0.0595 (8)
O40.3518 (2)0.08559 (14)0.06204 (10)0.0282 (5)
O50.5397 (2)0.12614 (16)0.01064 (10)0.0312 (5)
O60.1959 (2)0.00279 (15)0.04408 (9)0.0260 (5)
O70.0297 (2)0.06576 (16)0.06158 (11)0.0336 (5)
C10.6045 (4)0.0293 (2)0.15256 (16)0.0339 (8)
H10.59860.02690.12640.041*
C20.7056 (4)0.0302 (3)0.20843 (19)0.0526 (11)
H20.76920.02300.21890.063*
C30.7098 (5)0.1112 (3)0.2480 (2)0.0649 (14)
H30.77270.11240.28730.078*
C40.6203 (4)0.1911 (3)0.22942 (18)0.0511 (11)
H40.62440.24740.25550.061*
C50.5245 (3)0.1869 (2)0.17185 (15)0.0273 (7)
C60.4332 (3)0.2729 (2)0.14606 (14)0.0239 (7)
C70.4569 (3)0.3668 (2)0.17249 (15)0.0281 (7)
H70.52320.37570.21030.034*
C80.3819 (3)0.4478 (2)0.14261 (15)0.0262 (7)
C90.2878 (3)0.4311 (2)0.08546 (15)0.0268 (7)
H90.23990.48430.06310.032*
C100.2640 (3)0.3362 (2)0.06115 (13)0.0236 (7)
C110.1652 (3)0.3154 (2)0.00079 (14)0.0237 (7)
C120.0955 (4)0.3907 (2)0.03979 (17)0.0383 (9)
H120.11140.45660.02780.046*
C130.0030 (4)0.3674 (3)0.09620 (17)0.0426 (9)
H130.04260.41700.12290.051*
C140.0199 (4)0.2698 (3)0.11177 (16)0.0411 (9)
H140.08450.25180.14860.049*
C150.0533 (4)0.1983 (2)0.07258 (16)0.0369 (9)
H150.03820.13220.08430.044*
C160.4074 (3)0.5518 (2)0.16699 (14)0.0267 (7)
C170.4716 (4)0.6171 (2)0.12774 (16)0.0343 (8)
H170.50070.59430.08920.041*
C180.4933 (4)0.7157 (2)0.14471 (17)0.0416 (9)
H180.54010.75790.11860.050*
C190.4459 (4)0.7508 (3)0.19991 (17)0.0443 (10)
H190.45650.81760.21060.053*
C200.3818 (4)0.6868 (2)0.24002 (16)0.0383 (9)
H200.34980.71110.27760.046*
C210.3648 (4)0.5873 (2)0.22509 (15)0.0288 (7)
C220.4072 (3)0.1327 (2)0.01827 (14)0.0229 (7)
C230.3100 (3)0.2031 (2)0.02505 (14)0.0238 (7)
C240.3610 (4)0.2990 (2)0.03245 (16)0.0320 (8)
H240.45280.31730.01070.038*
C250.2782 (4)0.3677 (2)0.07141 (18)0.0399 (9)
H250.31390.43170.07530.048*
C260.1423 (4)0.3410 (3)0.10450 (18)0.0442 (9)
H260.08720.38640.13150.053*
C270.0891 (4)0.2468 (3)0.09722 (16)0.0376 (8)
H270.00300.22950.11910.045*
C280.1703 (3)0.1769 (2)0.05762 (14)0.0263 (7)
C290.1071 (3)0.0750 (2)0.05374 (14)0.0240 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Eu10.01913 (9)0.01965 (9)0.02190 (9)0.00021 (6)0.00141 (6)0.00154 (6)
S10.0442 (5)0.0384 (5)0.0266 (4)0.0010 (4)0.0097 (4)0.0002 (4)
N10.0243 (14)0.0227 (14)0.0264 (14)0.0013 (11)0.0031 (11)0.0018 (11)
N20.0231 (13)0.0236 (14)0.0189 (13)0.0002 (11)0.0004 (11)0.0016 (11)
N30.0297 (15)0.0229 (15)0.0263 (14)0.0002 (11)0.0045 (12)0.0033 (11)
O10.0425 (15)0.0522 (16)0.0269 (12)0.0088 (12)0.0097 (11)0.0031 (11)
O20.0624 (19)0.080 (2)0.0431 (16)0.0362 (16)0.0077 (14)0.0057 (15)
O30.090 (2)0.0512 (17)0.0435 (16)0.0304 (15)0.0314 (15)0.0165 (13)
O40.0305 (12)0.0253 (12)0.0284 (12)0.0037 (10)0.0029 (10)0.0018 (9)
O50.0234 (13)0.0413 (14)0.0283 (12)0.0032 (10)0.0018 (10)0.0002 (10)
O60.0241 (12)0.0263 (12)0.0273 (12)0.0002 (9)0.0021 (9)0.0018 (9)
O70.0192 (12)0.0434 (15)0.0377 (13)0.0018 (10)0.0021 (10)0.0027 (10)
C10.0311 (19)0.0305 (19)0.040 (2)0.0044 (15)0.0033 (16)0.0005 (16)
C20.047 (2)0.037 (2)0.064 (3)0.0100 (18)0.026 (2)0.002 (2)
C30.070 (3)0.048 (3)0.061 (3)0.010 (2)0.043 (2)0.002 (2)
C40.064 (3)0.035 (2)0.045 (2)0.0021 (19)0.025 (2)0.0060 (17)
C50.0250 (17)0.0283 (18)0.0277 (17)0.0020 (14)0.0009 (14)0.0012 (14)
C60.0273 (17)0.0217 (17)0.0230 (16)0.0004 (13)0.0039 (13)0.0015 (13)
C70.0301 (18)0.0317 (19)0.0220 (16)0.0011 (14)0.0013 (14)0.0061 (14)
C80.0323 (18)0.0221 (17)0.0254 (17)0.0011 (13)0.0086 (14)0.0043 (13)
C90.0331 (19)0.0223 (18)0.0234 (16)0.0029 (14)0.0015 (14)0.0006 (13)
C100.0255 (17)0.0233 (17)0.0221 (16)0.0004 (13)0.0036 (13)0.0027 (13)
C110.0238 (17)0.0233 (17)0.0229 (16)0.0007 (13)0.0007 (13)0.0022 (13)
C120.047 (2)0.0245 (19)0.039 (2)0.0037 (16)0.0087 (17)0.0024 (15)
C130.051 (2)0.036 (2)0.035 (2)0.0100 (18)0.0150 (18)0.0030 (16)
C140.049 (2)0.037 (2)0.0307 (19)0.0029 (17)0.0159 (17)0.0022 (16)
C150.043 (2)0.0287 (19)0.035 (2)0.0006 (16)0.0083 (17)0.0044 (15)
C160.0327 (19)0.0224 (17)0.0219 (17)0.0012 (13)0.0063 (14)0.0009 (13)
C170.049 (2)0.0312 (19)0.0226 (17)0.0018 (16)0.0032 (16)0.0019 (14)
C180.053 (2)0.029 (2)0.041 (2)0.0054 (17)0.0013 (19)0.0103 (16)
C190.059 (3)0.0234 (19)0.048 (2)0.0010 (18)0.004 (2)0.0012 (18)
C200.049 (2)0.031 (2)0.034 (2)0.0071 (17)0.0000 (17)0.0121 (16)
C210.0296 (18)0.0291 (18)0.0261 (17)0.0018 (14)0.0015 (14)0.0028 (14)
C220.0273 (18)0.0183 (16)0.0222 (16)0.0011 (13)0.0001 (14)0.0057 (13)
C230.0246 (17)0.0249 (17)0.0234 (16)0.0044 (13)0.0089 (13)0.0008 (13)
C240.034 (2)0.0272 (19)0.0370 (19)0.0048 (14)0.0137 (16)0.0059 (15)
C250.048 (2)0.0196 (18)0.056 (2)0.0022 (16)0.0225 (19)0.0075 (17)
C260.049 (2)0.034 (2)0.051 (2)0.0154 (18)0.0135 (19)0.0177 (18)
C270.0308 (19)0.038 (2)0.043 (2)0.0069 (16)0.0031 (16)0.0097 (17)
C280.0249 (17)0.0264 (18)0.0288 (18)0.0069 (13)0.0076 (14)0.0039 (14)
C290.0246 (17)0.0315 (18)0.0166 (15)0.0024 (14)0.0050 (13)0.0006 (13)
Geometric parameters (Å, º) top
Eu1—O7i2.302 (2)C7—H70.9300
Eu1—O42.339 (2)C8—C91.382 (4)
Eu1—O62.3553 (19)C8—C161.499 (4)
Eu1—O5ii2.374 (2)C9—C101.383 (4)
Eu1—O1iii2.411 (2)C9—H90.9300
Eu1—N22.533 (2)C10—C111.491 (4)
Eu1—N12.567 (2)C11—C121.396 (4)
Eu1—N32.592 (2)C12—C131.381 (4)
S1—O31.435 (3)C12—H120.9300
S1—O21.444 (3)C13—C141.365 (5)
S1—O11.474 (2)C13—H130.9300
S1—C211.785 (3)C14—C151.374 (4)
N1—C11.329 (4)C14—H140.9300
N1—C51.351 (4)C15—H150.9300
N2—C101.355 (4)C16—C171.385 (5)
N2—C61.368 (3)C16—C211.401 (4)
N3—C111.345 (4)C17—C181.383 (4)
N3—C151.349 (4)C17—H170.9300
O1—Eu1iv2.411 (2)C18—C191.364 (5)
O4—C221.270 (4)C18—H180.9300
O5—C221.249 (4)C19—C201.385 (5)
O5—Eu1ii2.374 (2)C19—H190.9300
O6—C291.267 (3)C20—C211.382 (4)
O7—C291.247 (4)C20—H200.9300
O7—Eu1i2.302 (2)C22—C231.510 (4)
C1—C21.378 (4)C23—C241.391 (4)
C1—H10.9300C23—C281.406 (4)
C2—C31.364 (5)C24—C251.384 (4)
C2—H20.9300C24—H240.9300
C3—C41.376 (5)C25—C261.382 (5)
C3—H30.9300C25—H250.9300
C4—C51.380 (4)C26—C271.377 (5)
C4—H40.9300C26—H260.9300
C5—C61.485 (4)C27—C281.396 (4)
C6—C71.385 (4)C27—H270.9300
C7—C81.389 (4)C28—C291.499 (4)
O7i—Eu1—O4101.21 (8)C8—C7—H7119.9
O7i—Eu1—O679.65 (7)C9—C8—C7117.7 (3)
O4—Eu1—O669.98 (7)C9—C8—C16119.3 (3)
O7i—Eu1—O5ii147.09 (7)C7—C8—C16122.8 (3)
O4—Eu1—O5ii93.77 (8)C10—C9—C8120.7 (3)
O6—Eu1—O5ii78.24 (7)C10—C9—H9119.7
O7i—Eu1—O1iii71.09 (8)C8—C9—H9119.7
O4—Eu1—O1iii87.18 (8)N2—C10—C9121.5 (3)
O6—Eu1—O1iii138.43 (7)N2—C10—C11116.2 (2)
O5ii—Eu1—O1iii139.42 (7)C9—C10—C11122.2 (3)
O7i—Eu1—N2102.45 (8)N3—C11—C12120.9 (3)
O4—Eu1—N2146.57 (7)N3—C11—C10116.7 (3)
O6—Eu1—N2137.65 (7)C12—C11—C10122.4 (3)
O5ii—Eu1—N278.68 (8)C13—C12—C11120.1 (3)
O1iii—Eu1—N278.59 (7)C13—C12—H12120.0
O7i—Eu1—N1136.33 (8)C11—C12—H12120.0
O4—Eu1—N182.30 (7)C14—C13—C12118.4 (3)
O6—Eu1—N1139.26 (7)C14—C13—H13120.8
O5ii—Eu1—N174.33 (7)C12—C13—H13120.8
O1iii—Eu1—N165.59 (8)C13—C14—C15119.4 (3)
N2—Eu1—N164.28 (7)C13—C14—H14120.3
O7i—Eu1—N373.63 (8)C15—C14—H14120.3
O4—Eu1—N3147.24 (7)N3—C15—C14123.0 (3)
O6—Eu1—N377.29 (7)N3—C15—H15118.5
O5ii—Eu1—N377.92 (8)C14—C15—H15118.5
O1iii—Eu1—N3119.72 (8)C17—C16—C21118.7 (3)
N2—Eu1—N363.41 (7)C17—C16—C8117.2 (3)
N1—Eu1—N3124.23 (8)C21—C16—C8124.1 (3)
O3—S1—O2115.50 (19)C18—C17—C16121.4 (3)
O3—S1—O1111.61 (15)C18—C17—H17119.3
O2—S1—O1112.73 (16)C16—C17—H17119.3
O3—S1—C21106.56 (16)C19—C18—C17119.7 (3)
O2—S1—C21105.18 (15)C19—C18—H18120.2
O1—S1—C21104.17 (14)C17—C18—H18120.2
C1—N1—C5118.5 (3)C18—C19—C20119.9 (3)
C1—N1—Eu1121.3 (2)C18—C19—H19120.1
C5—N1—Eu1117.26 (19)C20—C19—H19120.1
C10—N2—C6118.3 (2)C21—C20—C19121.0 (3)
C10—N2—Eu1122.67 (17)C21—C20—H20119.5
C6—N2—Eu1119.01 (18)C19—C20—H20119.5
C11—N3—C15118.1 (3)C20—C21—C16119.2 (3)
C11—N3—Eu1120.76 (18)C20—C21—S1120.3 (3)
C15—N3—Eu1121.1 (2)C16—C21—S1120.4 (2)
S1—O1—Eu1iv147.33 (14)O5—C22—O4123.2 (3)
C22—O4—Eu1124.86 (18)O5—C22—C23118.2 (3)
C22—O5—Eu1ii149.99 (19)O4—C22—C23118.6 (3)
C29—O6—Eu1128.43 (19)C24—C23—C28118.6 (3)
C29—O7—Eu1i164.6 (2)C24—C23—C22118.2 (3)
N1—C1—C2123.2 (3)C28—C23—C22123.3 (3)
N1—C1—H1118.4C25—C24—C23121.5 (3)
C2—C1—H1118.4C25—C24—H24119.2
C3—C2—C1118.1 (3)C23—C24—H24119.2
C3—C2—H2120.9C26—C25—C24119.8 (3)
C1—C2—H2120.9C26—C25—H25120.1
C2—C3—C4119.6 (3)C24—C25—H25120.1
C2—C3—H3120.2C27—C26—C25119.6 (3)
C4—C3—H3120.2C27—C26—H26120.2
C3—C4—C5119.5 (3)C25—C26—H26120.2
C3—C4—H4120.3C26—C27—C28121.4 (3)
C5—C4—H4120.3C26—C27—H27119.3
N1—C5—C4120.9 (3)C28—C27—H27119.3
N1—C5—C6116.5 (2)C27—C28—C23119.2 (3)
C4—C5—C6122.5 (3)C27—C28—C29118.3 (3)
N2—C6—C7121.4 (3)C23—C28—C29122.5 (3)
N2—C6—C5116.9 (3)O7—C29—O6123.7 (3)
C7—C6—C5121.5 (3)O7—C29—C28118.3 (3)
C6—C7—C8120.2 (3)O6—C29—C28118.0 (3)
C6—C7—H7119.9
O3—S1—O1—Eu1iv39.7 (3)C9—C8—C16—C1762.4 (4)
O2—S1—O1—Eu1iv92.3 (3)C7—C8—C16—C17112.9 (3)
C21—S1—O1—Eu1iv154.2 (3)C9—C8—C16—C21114.8 (4)
C5—N1—C1—C20.7 (5)C7—C8—C16—C2170.0 (4)
Eu1—N1—C1—C2159.3 (3)C21—C16—C17—C180.3 (5)
N1—C1—C2—C32.6 (6)C8—C16—C17—C18177.0 (3)
C1—C2—C3—C43.7 (7)C16—C17—C18—C192.5 (5)
C2—C3—C4—C51.8 (7)C17—C18—C19—C202.7 (5)
C1—N1—C5—C42.7 (5)C18—C19—C20—C210.1 (5)
Eu1—N1—C5—C4158.1 (3)C19—C20—C21—C162.8 (5)
C1—N1—C5—C6174.1 (3)C19—C20—C21—S1179.7 (3)
Eu1—N1—C5—C625.2 (3)C17—C16—C21—C202.9 (5)
C3—C4—C5—N11.4 (6)C8—C16—C21—C20174.2 (3)
C3—C4—C5—C6175.1 (4)C17—C16—C21—S1179.6 (2)
C10—N2—C6—C75.4 (4)C8—C16—C21—S13.3 (4)
Eu1—N2—C6—C7173.5 (2)O3—S1—C21—C20120.8 (3)
C10—N2—C6—C5169.8 (3)O2—S1—C21—C20116.1 (3)
Eu1—N2—C6—C511.3 (3)O1—S1—C21—C202.7 (3)
N1—C5—C6—N29.4 (4)O3—S1—C21—C1661.7 (3)
C4—C5—C6—N2173.9 (3)O2—S1—C21—C1661.4 (3)
N1—C5—C6—C7165.7 (3)O1—S1—C21—C16179.9 (2)
C4—C5—C6—C711.0 (5)Eu1ii—O5—C22—O4116.2 (4)
N2—C6—C7—C82.5 (5)Eu1ii—O5—C22—C2366.3 (5)
C5—C6—C7—C8172.3 (3)Eu1—O4—C22—O580.8 (3)
C6—C7—C8—C91.8 (5)Eu1—O4—C22—C23101.7 (3)
C6—C7—C8—C16177.2 (3)O5—C22—C23—C2448.2 (4)
C7—C8—C9—C103.3 (5)O4—C22—C23—C24129.4 (3)
C16—C8—C9—C10178.9 (3)O5—C22—C23—C28132.5 (3)
C6—N2—C10—C93.8 (4)O4—C22—C23—C2849.9 (4)
Eu1—N2—C10—C9175.0 (2)C28—C23—C24—C250.7 (5)
C6—N2—C10—C11174.8 (3)C22—C23—C24—C25179.9 (3)
Eu1—N2—C10—C116.3 (3)C23—C24—C25—C260.7 (5)
C8—C9—C10—N20.5 (5)C24—C25—C26—C271.5 (5)
C8—C9—C10—C11179.1 (3)C25—C26—C27—C280.8 (5)
C15—N3—C11—C122.5 (5)C26—C27—C28—C230.6 (5)
Eu1—N3—C11—C12179.5 (2)C26—C27—C28—C29178.2 (3)
C15—N3—C11—C10177.8 (3)C24—C23—C28—C271.3 (4)
Eu1—N3—C11—C100.2 (4)C22—C23—C28—C27179.3 (3)
N2—C10—C11—N34.1 (4)C24—C23—C28—C29178.8 (3)
C9—C10—C11—N3177.2 (3)C22—C23—C28—C291.9 (5)
N2—C10—C11—C12175.6 (3)Eu1i—O7—C29—O6128.2 (7)
C9—C10—C11—C123.0 (5)Eu1i—O7—C29—C2853.4 (9)
N3—C11—C12—C131.4 (5)Eu1—O6—C29—O782.2 (3)
C10—C11—C12—C13178.9 (3)Eu1—O6—C29—C2899.4 (3)
C11—C12—C13—C141.1 (6)C27—C28—C29—O729.2 (4)
C12—C13—C14—C152.4 (6)C23—C28—C29—O7153.3 (3)
C11—N3—C15—C141.2 (5)C27—C28—C29—O6149.3 (3)
Eu1—N3—C15—C14179.1 (3)C23—C28—C29—O628.2 (4)
C13—C14—C15—N31.3 (6)
Symmetry codes: (i) x, y, z; (ii) x+1, y, z; (iii) x+1/2, y1/2, z+1/2; (iv) x+1/2, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···O60.932.403.034 (4)125
C1—H1···O40.932.583.173 (4)122
C15—H15···O60.932.403.034 (4)125
C1—H1···O40.932.583.173 (4)122
C1—H1···O40.932.583.173 (4)122
C15—H15···O60.932.403.034 (4)125
(7) top
Crystal data top
C29H18N3O7STbF(000) = 1400
Mr = 711.44Dx = 1.879 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 9.119 (1) ÅCell parameters from 5396 reflections
b = 13.4630 (15) Åθ = 2.5–26.7°
c = 20.674 (2) ŵ = 2.95 mm1
β = 97.756 (2)°T = 296 K
V = 2514.8 (5) Å3Block, yellow
Z = 40.22 × 0.18 × 0.16 mm
Data collection top
Bruker APEX-II CCD
diffractometer
3901 reflections with I > 2σ(I)
φ and ω scansRint = 0.027
Absorption correction: multi-scan
sadabs
θmax = 25.1°, θmin = 2.0°
Tmin = 0.533, Tmax = 0.625h = 1010
12344 measured reflectionsk = 1515
4429 independent reflectionsl = 1024
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.022H-atom parameters constrained
wR(F2) = 0.050 w = 1/[σ2(Fo2) + (0.0202P)2 + 1.1962P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
4429 reflectionsΔρmax = 0.47 e Å3
370 parametersΔρmin = 0.51 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
Tb10.27704 (2)0.91890 (2)0.55400 (2)0.01927 (6)
S10.28374 (10)0.49291 (7)0.77860 (4)0.0339 (2)
N10.5138 (3)0.89674 (18)0.63338 (13)0.0236 (6)
N20.3318 (3)0.74370 (18)0.59182 (12)0.0219 (6)
N30.1464 (3)0.78131 (18)0.48184 (12)0.0260 (6)
O10.2576 (3)0.42859 (18)0.83338 (11)0.0376 (6)
O20.3915 (3)0.56879 (19)0.79881 (13)0.0567 (8)
O30.1486 (3)0.5273 (2)0.74090 (13)0.0601 (8)
O40.3509 (2)1.08309 (15)0.56182 (10)0.0257 (5)
O50.5405 (2)1.12528 (16)0.51044 (10)0.0281 (5)
O60.1957 (2)1.00117 (15)0.45648 (10)0.0247 (5)
O70.0307 (2)1.06443 (17)0.43899 (11)0.0314 (5)
C10.6037 (3)0.9724 (3)0.65144 (17)0.0313 (8)
H10.59721.02880.62530.038*
C20.7057 (4)0.9716 (3)0.7066 (2)0.0491 (11)
H20.76911.02520.71690.059*
C30.7116 (5)0.8902 (3)0.7460 (2)0.0628 (14)
H30.77680.88860.78470.075*
C40.6210 (4)0.8105 (3)0.72836 (19)0.0482 (11)
H40.62530.75430.75470.058*
C50.5238 (3)0.8143 (2)0.67129 (15)0.0252 (7)
C60.4321 (3)0.7282 (2)0.64597 (15)0.0233 (7)
C70.4566 (3)0.6341 (2)0.67247 (15)0.0269 (7)
H70.52330.62530.71020.032*
C80.3818 (3)0.5530 (2)0.64268 (15)0.0252 (7)
C90.2881 (3)0.5693 (2)0.58528 (16)0.0266 (7)
H90.24090.51590.56290.032*
C100.2639 (3)0.6648 (2)0.56081 (14)0.0234 (7)
C110.1650 (3)0.6850 (2)0.49866 (15)0.0234 (7)
C120.0964 (4)0.6096 (3)0.46006 (18)0.0381 (9)
H120.11280.54360.47230.046*
C130.0038 (4)0.6323 (3)0.40355 (18)0.0416 (9)
H130.04130.58240.37680.050*
C140.0200 (4)0.7311 (3)0.38779 (18)0.0418 (9)
H140.08480.74920.35100.050*
C150.0537 (4)0.8026 (3)0.42731 (17)0.0346 (8)
H150.03860.86900.41570.042*
C160.4085 (3)0.4486 (2)0.66687 (15)0.0254 (7)
C170.4740 (4)0.3834 (3)0.62709 (17)0.0336 (8)
H170.50340.40700.58860.040*
C180.4964 (4)0.2844 (3)0.64344 (18)0.0387 (9)
H180.54390.24260.61710.046*
C190.4477 (4)0.2486 (3)0.69914 (18)0.0421 (9)
H190.45800.18150.70950.051*
C200.3833 (4)0.3122 (2)0.73981 (17)0.0355 (8)
H200.35150.28730.77750.043*
C210.3654 (3)0.4124 (2)0.72516 (15)0.0266 (7)
C220.4061 (3)1.1305 (2)0.51841 (15)0.0230 (7)
C230.3092 (3)1.2023 (2)0.47531 (15)0.0224 (7)
C240.3608 (4)1.2985 (2)0.46803 (17)0.0305 (8)
H240.45261.31700.48980.037*
C250.2777 (4)1.3668 (3)0.42897 (19)0.0392 (9)
H250.31351.43090.42520.047*
C260.1418 (4)1.3405 (3)0.39552 (19)0.0435 (10)
H260.08701.38590.36820.052*
C270.0886 (4)1.2460 (3)0.40317 (17)0.0352 (8)
H270.00381.22870.38140.042*
C280.1694 (3)1.1757 (2)0.44265 (15)0.0249 (7)
C290.1068 (3)1.0733 (2)0.44688 (15)0.0232 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Tb10.01796 (9)0.01908 (9)0.02058 (9)0.00035 (6)0.00197 (6)0.00155 (7)
S10.0415 (5)0.0356 (5)0.0262 (5)0.0004 (4)0.0101 (4)0.0008 (4)
N10.0236 (14)0.0245 (14)0.0230 (14)0.0011 (11)0.0047 (11)0.0023 (12)
N20.0213 (13)0.0238 (14)0.0202 (14)0.0002 (11)0.0012 (11)0.0026 (12)
N30.0299 (15)0.0228 (15)0.0235 (14)0.0011 (11)0.0030 (12)0.0025 (12)
O10.0373 (14)0.0520 (16)0.0245 (13)0.0091 (11)0.0082 (11)0.0034 (12)
O20.086 (2)0.0462 (17)0.0434 (17)0.0274 (15)0.0304 (15)0.0157 (14)
O30.0606 (19)0.076 (2)0.0446 (17)0.0347 (16)0.0095 (14)0.0041 (16)
O40.0306 (12)0.0225 (12)0.0238 (12)0.0053 (9)0.0032 (9)0.0021 (10)
O50.0227 (12)0.0356 (13)0.0261 (12)0.0054 (10)0.0031 (10)0.0017 (10)
O60.0246 (11)0.0238 (12)0.0255 (12)0.0006 (9)0.0026 (9)0.0018 (10)
O70.0185 (12)0.0404 (14)0.0348 (14)0.0010 (10)0.0018 (10)0.0032 (11)
C10.0267 (18)0.0306 (19)0.037 (2)0.0026 (15)0.0038 (15)0.0022 (16)
C20.039 (2)0.036 (2)0.066 (3)0.0114 (17)0.021 (2)0.001 (2)
C30.066 (3)0.048 (3)0.060 (3)0.008 (2)0.043 (2)0.004 (2)
C40.062 (3)0.036 (2)0.039 (2)0.0028 (19)0.022 (2)0.0065 (18)
C50.0272 (17)0.0223 (17)0.0251 (18)0.0014 (13)0.0004 (14)0.0024 (14)
C60.0249 (16)0.0269 (18)0.0184 (16)0.0000 (13)0.0034 (13)0.0010 (14)
C70.0304 (18)0.0292 (18)0.0196 (17)0.0036 (14)0.0016 (14)0.0041 (14)
C80.0299 (18)0.0242 (17)0.0227 (17)0.0025 (13)0.0081 (14)0.0017 (14)
C90.0321 (18)0.0222 (18)0.0246 (17)0.0048 (14)0.0010 (14)0.0004 (14)
C100.0231 (16)0.0258 (17)0.0219 (17)0.0008 (13)0.0055 (13)0.0023 (14)
C110.0240 (16)0.0247 (17)0.0209 (17)0.0003 (13)0.0012 (13)0.0015 (14)
C120.048 (2)0.0252 (19)0.038 (2)0.0050 (16)0.0064 (18)0.0025 (16)
C130.051 (2)0.033 (2)0.036 (2)0.0087 (17)0.0132 (18)0.0040 (17)
C140.046 (2)0.038 (2)0.035 (2)0.0032 (17)0.0158 (17)0.0010 (18)
C150.040 (2)0.0282 (19)0.032 (2)0.0034 (15)0.0083 (16)0.0021 (16)
C160.0278 (17)0.0229 (17)0.0236 (18)0.0002 (13)0.0035 (14)0.0023 (14)
C170.045 (2)0.0327 (19)0.0228 (18)0.0015 (16)0.0047 (16)0.0008 (15)
C180.048 (2)0.030 (2)0.037 (2)0.0026 (16)0.0020 (18)0.0118 (17)
C190.053 (2)0.0230 (19)0.048 (2)0.0000 (17)0.0026 (19)0.0022 (18)
C200.046 (2)0.030 (2)0.030 (2)0.0014 (16)0.0000 (17)0.0112 (16)
C210.0283 (17)0.0287 (18)0.0218 (17)0.0016 (14)0.0006 (14)0.0017 (15)
C220.0241 (17)0.0212 (16)0.0232 (17)0.0011 (13)0.0010 (14)0.0076 (14)
C230.0228 (16)0.0215 (17)0.0243 (17)0.0016 (13)0.0083 (13)0.0006 (14)
C240.0317 (19)0.0276 (19)0.034 (2)0.0003 (14)0.0118 (16)0.0019 (15)
C250.047 (2)0.0208 (19)0.054 (3)0.0046 (16)0.024 (2)0.0080 (17)
C260.046 (2)0.033 (2)0.052 (2)0.0127 (18)0.0116 (19)0.0209 (19)
C270.0287 (18)0.038 (2)0.039 (2)0.0068 (16)0.0039 (16)0.0113 (18)
C280.0235 (16)0.0289 (18)0.0237 (17)0.0051 (14)0.0079 (13)0.0013 (14)
C290.0221 (17)0.0306 (18)0.0167 (16)0.0012 (14)0.0024 (13)0.0003 (14)
Geometric parameters (Å, º) top
Tb1—O7i2.281 (2)C7—H70.9300
Tb1—O42.310 (2)C8—C91.383 (4)
Tb1—O62.332 (2)C8—C161.501 (4)
Tb1—O5ii2.344 (2)C9—C101.388 (4)
Tb1—O1iii2.395 (2)C9—H90.9300
Tb1—N22.514 (2)C10—C111.492 (4)
Tb1—N12.547 (3)C11—C121.387 (4)
Tb1—N32.568 (3)C12—C131.380 (5)
S1—O21.440 (3)C12—H120.9300
S1—O31.442 (3)C13—C141.380 (5)
S1—O11.470 (2)C13—H130.9300
S1—C211.781 (3)C14—C151.377 (5)
N1—C11.329 (4)C14—H140.9300
N1—C51.355 (4)C15—H150.9300
N2—C101.347 (4)C16—C171.391 (5)
N2—C61.363 (4)C16—C211.405 (4)
N3—C151.346 (4)C17—C181.384 (5)
N3—C111.347 (4)C17—H170.9300
O1—Tb1iv2.395 (2)C18—C191.376 (5)
O4—C221.260 (4)C18—H180.9300
O5—C221.260 (4)C19—C201.385 (5)
O5—Tb1ii2.344 (2)C19—H190.9300
O6—C291.263 (4)C20—C211.387 (4)
O7—C291.249 (4)C20—H200.9300
O7—Tb1i2.281 (2)C22—C231.515 (4)
C1—C21.371 (5)C23—C241.392 (4)
C1—H10.9300C23—C281.406 (4)
C2—C31.362 (6)C24—C251.381 (5)
C2—H20.9300C24—H240.9300
C3—C41.374 (5)C25—C261.381 (5)
C3—H30.9300C25—H250.9300
C4—C51.378 (4)C26—C271.379 (5)
C4—H40.9300C26—H260.9300
C5—C61.483 (4)C27—C281.394 (4)
C6—C71.387 (4)C27—H270.9300
C7—C81.387 (4)C28—C291.499 (4)
O7i—Tb1—O4100.47 (8)C8—C7—H7120.0
O7i—Tb1—O678.87 (8)C9—C8—C7117.8 (3)
O4—Tb1—O670.23 (7)C9—C8—C16119.3 (3)
O7i—Tb1—O5ii147.30 (8)C7—C8—C16122.8 (3)
O4—Tb1—O5ii93.43 (8)C8—C9—C10120.6 (3)
O6—Tb1—O5ii78.27 (7)C8—C9—H9119.7
O7i—Tb1—O1iii70.91 (8)C10—C9—H9119.7
O4—Tb1—O1iii87.44 (8)N2—C10—C9121.1 (3)
O6—Tb1—O1iii138.27 (7)N2—C10—C11116.9 (3)
O5ii—Tb1—O1iii139.73 (8)C9—C10—C11122.0 (3)
O7i—Tb1—N2103.20 (8)N3—C11—C12121.7 (3)
O4—Tb1—N2146.34 (8)N3—C11—C10116.0 (3)
O6—Tb1—N2137.84 (8)C12—C11—C10122.4 (3)
O5ii—Tb1—N279.19 (8)C13—C12—C11120.1 (3)
O1iii—Tb1—N278.19 (8)C13—C12—H12120.0
O7i—Tb1—N1136.62 (8)C11—C12—H12120.0
O4—Tb1—N181.55 (8)C14—C13—C12118.2 (3)
O6—Tb1—N1139.10 (8)C14—C13—H13120.9
O5ii—Tb1—N174.43 (8)C12—C13—H13120.9
O1iii—Tb1—N165.88 (8)C15—C14—C13119.0 (3)
N2—Tb1—N164.80 (8)C15—C14—H14120.5
O7i—Tb1—N374.00 (8)C13—C14—H14120.5
O4—Tb1—N3147.01 (8)N3—C15—C14123.3 (3)
O6—Tb1—N376.81 (8)N3—C15—H15118.4
O5ii—Tb1—N378.24 (8)C14—C15—H15118.4
O1iii—Tb1—N3119.49 (8)C17—C16—C21118.7 (3)
N2—Tb1—N363.96 (8)C17—C16—C8117.2 (3)
N1—Tb1—N3125.18 (8)C21—C16—C8124.0 (3)
O2—S1—O3115.39 (19)C18—C17—C16121.6 (3)
O2—S1—O1111.70 (16)C18—C17—H17119.2
O3—S1—O1112.94 (17)C16—C17—H17119.2
O2—S1—C21106.61 (16)C19—C18—C17119.2 (3)
O3—S1—C21104.98 (16)C19—C18—H18120.4
O1—S1—C21104.12 (15)C17—C18—H18120.4
C1—N1—C5118.3 (3)C18—C19—C20120.2 (3)
C1—N1—Tb1121.9 (2)C18—C19—H19119.9
C5—N1—Tb1116.99 (19)C20—C19—H19119.9
C10—N2—C6119.0 (3)C19—C20—C21121.0 (3)
C10—N2—Tb1122.17 (19)C19—C20—H20119.5
C6—N2—Tb1118.85 (19)C21—C20—H20119.5
C15—N3—C11117.7 (3)C20—C21—C16119.1 (3)
C15—N3—Tb1121.5 (2)C20—C21—S1120.2 (3)
C11—N3—Tb1120.8 (2)C16—C21—S1120.7 (2)
S1—O1—Tb1iv146.84 (15)O5—C22—O4123.6 (3)
C22—O4—Tb1125.14 (19)O5—C22—C23117.3 (3)
C22—O5—Tb1ii150.0 (2)O4—C22—C23119.0 (3)
C29—O6—Tb1128.58 (19)C24—C23—C28118.8 (3)
C29—O7—Tb1i164.3 (2)C24—C23—C22118.6 (3)
N1—C1—C2123.5 (3)C28—C23—C22122.6 (3)
N1—C1—H1118.2C25—C24—C23121.1 (3)
C2—C1—H1118.2C25—C24—H24119.5
C3—C2—C1118.1 (3)C23—C24—H24119.5
C3—C2—H2121.0C24—C25—C26120.4 (3)
C1—C2—H2121.0C24—C25—H25119.8
C2—C3—C4119.8 (4)C26—C25—H25119.8
C2—C3—H3120.1C27—C26—C25119.0 (3)
C4—C3—H3120.1C27—C26—H26120.5
C3—C4—C5119.5 (4)C25—C26—H26120.5
C3—C4—H4120.2C26—C27—C28121.8 (3)
C5—C4—H4120.2C26—C27—H27119.1
N1—C5—C4120.7 (3)C28—C27—H27119.1
N1—C5—C6116.5 (3)C27—C28—C23118.8 (3)
C4—C5—C6122.7 (3)C27—C28—C29118.9 (3)
N2—C6—C7121.3 (3)C23—C28—C29122.3 (3)
N2—C6—C5117.0 (3)O7—C29—O6124.0 (3)
C7—C6—C5121.5 (3)O7—C29—C28117.7 (3)
C6—C7—C8120.0 (3)O6—C29—C28118.4 (3)
C6—C7—H7120.0
O2—S1—O1—Tb1iv41.9 (3)C9—C8—C16—C1761.9 (4)
O3—S1—O1—Tb1iv90.2 (3)C7—C8—C16—C17112.5 (4)
C21—S1—O1—Tb1iv156.5 (2)C9—C8—C16—C21115.1 (4)
C5—N1—C1—C20.4 (5)C7—C8—C16—C2170.5 (4)
Tb1—N1—C1—C2160.2 (3)C21—C16—C17—C180.4 (5)
N1—C1—C2—C32.2 (6)C8—C16—C17—C18176.7 (3)
C1—C2—C3—C42.7 (7)C16—C17—C18—C192.5 (5)
C2—C3—C4—C50.8 (7)C17—C18—C19—C203.0 (5)
C1—N1—C5—C42.4 (5)C18—C19—C20—C210.6 (5)
Tb1—N1—C5—C4159.2 (3)C19—C20—C21—C162.4 (5)
C1—N1—C5—C6174.1 (3)C19—C20—C21—S1179.4 (3)
Tb1—N1—C5—C624.4 (3)C17—C16—C21—C202.8 (5)
C3—C4—C5—N11.8 (6)C8—C16—C21—C20174.0 (3)
C3—C4—C5—C6174.4 (4)C17—C16—C21—S1179.0 (2)
C10—N2—C6—C75.2 (4)C8—C16—C21—S14.1 (4)
Tb1—N2—C6—C7174.0 (2)O2—S1—C21—C20121.1 (3)
C10—N2—C6—C5169.0 (3)O3—S1—C21—C20116.1 (3)
Tb1—N2—C6—C511.7 (3)O1—S1—C21—C202.8 (3)
N1—C5—C6—N28.7 (4)O2—S1—C21—C1660.8 (3)
C4—C5—C6—N2174.9 (3)O3—S1—C21—C1662.1 (3)
N1—C5—C6—C7165.5 (3)O1—S1—C21—C16179.0 (3)
C4—C5—C6—C710.9 (5)Tb1ii—O5—C22—O4115.5 (4)
N2—C6—C7—C82.0 (5)Tb1ii—O5—C22—C2367.9 (5)
C5—C6—C7—C8171.9 (3)Tb1—O4—C22—O581.4 (3)
C6—C7—C8—C92.4 (5)Tb1—O4—C22—C23102.0 (3)
C6—C7—C8—C16176.9 (3)O5—C22—C23—C2447.2 (4)
C7—C8—C9—C103.7 (5)O4—C22—C23—C24129.6 (3)
C16—C8—C9—C10178.4 (3)O5—C22—C23—C28133.0 (3)
C6—N2—C10—C93.8 (4)O4—C22—C23—C2850.2 (4)
Tb1—N2—C10—C9175.4 (2)C28—C23—C24—C250.7 (5)
C6—N2—C10—C11174.9 (3)C22—C23—C24—C25179.5 (3)
Tb1—N2—C10—C115.9 (3)C23—C24—C25—C260.8 (5)
C8—C9—C10—N20.6 (5)C24—C25—C26—C271.8 (6)
C8—C9—C10—C11179.3 (3)C25—C26—C27—C281.3 (6)
C15—N3—C11—C122.7 (5)C26—C27—C28—C230.2 (5)
Tb1—N3—C11—C12179.4 (3)C26—C27—C28—C29178.0 (3)
C15—N3—C11—C10177.6 (3)C24—C23—C28—C271.2 (5)
Tb1—N3—C11—C100.2 (4)C22—C23—C28—C27179.0 (3)
N2—C10—C11—N33.9 (4)C24—C23—C28—C29178.9 (3)
C9—C10—C11—N3177.4 (3)C22—C23—C28—C291.3 (5)
N2—C10—C11—C12175.8 (3)Tb1i—O7—C29—O6129.9 (7)
C9—C10—C11—C122.9 (5)Tb1i—O7—C29—C2852.0 (9)
N3—C11—C12—C131.5 (5)Tb1—O6—C29—O782.5 (4)
C10—C11—C12—C13178.9 (3)Tb1—O6—C29—C2899.4 (3)
C11—C12—C13—C141.2 (6)C27—C28—C29—O729.0 (4)
C12—C13—C14—C152.6 (6)C23—C28—C29—O7153.3 (3)
C11—N3—C15—C141.2 (5)C27—C28—C29—O6149.2 (3)
Tb1—N3—C15—C14179.1 (3)C23—C28—C29—O628.5 (4)
C13—C14—C15—N31.4 (6)
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y+2, z+1; (iii) x+1/2, y+1/2, z+3/2; (iv) x+1/2, y1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···O60.932.372.996 (4)125
C1—H1···O40.932.553.133 (4)121
 

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