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
CCDC references: 1536340; 1536341; 1536342; 1536343; 1536344; 1536345; 1536346
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.
Crystal data top
C26H20EuN3O7S | F(000) = 1328 |
Mr = 670.47 | Dx = 1.693 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.9849 (12) Å | Cell parameters from 5562 reflections |
b = 13.1957 (11) Å | θ = 2.3–26.3° |
c = 15.1425 (13) Å | µ = 2.51 mm−1 |
β = 109.763 (1)° | T = 296 K |
V = 2629.8 (4) Å3 | Block, yellow |
Z = 4 | 0.18 × 0.16 × 0.12 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 3915 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.029 |
Absorption correction: multi-scan sadabs | θmax = 25.1°, θmin = 2.2° |
Tmin = 0.64, Tmax = 0.742 | h = −16→11 |
13035 measured reflections | k = −13→15 |
4645 independent reflections | l = −18→16 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.024 | H-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 reflections | Δρmax = 0.97 e Å−3 |
343 parameters | Δρmin = −0.42 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Eu1 | 0.63574 (2) | 0.42545 (2) | 0.53001 (2) | 0.01543 (6) | |
S1 | 0.88491 (7) | 0.17050 (7) | 0.19280 (7) | 0.0269 (2) | |
N1 | 0.7823 (2) | 0.5522 (2) | 0.5446 (2) | 0.0225 (7) | |
N2 | 0.7476 (2) | 0.3936 (2) | 0.42842 (19) | 0.0202 (7) | |
N3 | 0.6518 (2) | 0.2374 (2) | 0.4749 (2) | 0.0260 (7) | |
O1 | 0.77829 (18) | 0.13743 (18) | 0.15226 (17) | 0.0268 (6) | |
O2 | 0.9505 (2) | 0.1164 (2) | 0.1531 (2) | 0.0439 (8) | |
O3 | 0.9179 (2) | 0.1711 (2) | 0.29345 (18) | 0.0372 (7) | |
O4 | 0.5618 (2) | 0.31558 (18) | 0.61858 (17) | 0.0285 (6) | |
O5 | 0.4442 (2) | 0.42007 (18) | 0.53665 (17) | 0.0300 (6) | |
O6 | 0.36890 (18) | 0.03009 (18) | 0.84260 (16) | 0.0228 (5) | |
O7 | 0.5175 (2) | 0.1113 (2) | 0.87794 (18) | 0.0397 (7) | |
C1 | 0.8076 (3) | 0.6227 (3) | 0.6111 (3) | 0.0364 (10) | |
H1 | 0.7730 | 0.6236 | 0.6539 | 0.044* | |
C2 | 0.8818 (3) | 0.6948 (3) | 0.6206 (3) | 0.0431 (11) | |
H2 | 0.8963 | 0.7433 | 0.6679 | 0.052* | |
C3 | 0.9334 (4) | 0.6929 (3) | 0.5587 (3) | 0.0453 (12) | |
H3 | 0.9839 | 0.7403 | 0.5630 | 0.054* | |
C4 | 0.9098 (3) | 0.6199 (3) | 0.4897 (3) | 0.0398 (11) | |
H4 | 0.9441 | 0.6177 | 0.4467 | 0.048* | |
C5 | 0.8343 (3) | 0.5497 (3) | 0.4849 (2) | 0.0210 (8) | |
C6 | 0.8088 (3) | 0.4668 (3) | 0.4147 (2) | 0.0210 (8) | |
C7 | 0.8480 (3) | 0.4623 (3) | 0.3425 (3) | 0.0289 (9) | |
H7 | 0.8937 | 0.5115 | 0.3377 | 0.035* | |
C8 | 0.8191 (3) | 0.3839 (3) | 0.2764 (3) | 0.0276 (9) | |
C9 | 0.7560 (3) | 0.3102 (3) | 0.2910 (2) | 0.0262 (9) | |
H9 | 0.7331 | 0.2580 | 0.2478 | 0.031* | |
C10 | 0.7267 (3) | 0.3135 (3) | 0.3695 (2) | 0.0215 (8) | |
C11 | 0.6783 (3) | 0.2250 (3) | 0.3980 (2) | 0.0226 (8) | |
C12 | 0.6703 (3) | 0.1329 (3) | 0.3528 (3) | 0.0392 (11) | |
H12 | 0.6892 | 0.1265 | 0.2998 | 0.047* | |
C13 | 0.6341 (5) | 0.0507 (3) | 0.3874 (4) | 0.0611 (16) | |
H13 | 0.6261 | −0.0115 | 0.3569 | 0.073* | |
C14 | 0.6102 (5) | 0.0614 (3) | 0.4668 (4) | 0.0604 (15) | |
H14 | 0.5885 | 0.0058 | 0.4927 | 0.072* | |
C15 | 0.6181 (4) | 0.1553 (3) | 0.5086 (3) | 0.0419 (11) | |
H15 | 0.5996 | 0.1623 | 0.5618 | 0.050* | |
C16 | 0.8546 (3) | 0.3852 (3) | 0.1943 (3) | 0.0315 (9) | |
C17 | 0.8608 (4) | 0.4786 (3) | 0.1549 (3) | 0.0480 (13) | |
H17 | 0.8457 | 0.5366 | 0.1825 | 0.058* | |
C18 | 0.8889 (4) | 0.4890 (4) | 0.0754 (3) | 0.0598 (15) | |
H18 | 0.8920 | 0.5529 | 0.0507 | 0.072* | |
C19 | 0.9117 (4) | 0.4052 (4) | 0.0340 (3) | 0.0547 (14) | |
H19 | 0.9285 | 0.4112 | −0.0202 | 0.066* | |
C20 | 0.9096 (3) | 0.3113 (3) | 0.0734 (3) | 0.0409 (11) | |
H20 | 0.9268 | 0.2544 | 0.0457 | 0.049* | |
C21 | 0.8827 (3) | 0.2991 (3) | 0.1527 (3) | 0.0293 (9) | |
C22 | 0.4740 (3) | 0.3506 (3) | 0.5981 (2) | 0.0225 (8) | |
C23 | 0.4030 (3) | 0.3105 (3) | 0.6448 (3) | 0.0382 (11) | |
H23A | 0.3398 | 0.2909 | 0.5968 | 0.046* | |
H23B | 0.3876 | 0.3644 | 0.6815 | 0.046* | |
C24 | 0.4437 (3) | 0.2212 (3) | 0.7078 (3) | 0.0333 (10) | |
H24A | 0.5085 | 0.2401 | 0.7538 | 0.040* | |
H24B | 0.4564 | 0.1666 | 0.6704 | 0.040* | |
C25 | 0.3759 (3) | 0.1816 (3) | 0.7593 (3) | 0.0317 (9) | |
H25A | 0.3147 | 0.1540 | 0.7138 | 0.038* | |
H25B | 0.3558 | 0.2379 | 0.7904 | 0.038* | |
C26 | 0.4249 (3) | 0.1003 (3) | 0.8319 (2) | 0.0234 (8) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Eu1 | 0.01755 (10) | 0.01500 (9) | 0.01540 (9) | 0.00035 (8) | 0.00777 (7) | 0.00000 (7) |
S1 | 0.0208 (5) | 0.0326 (5) | 0.0293 (5) | −0.0056 (4) | 0.0112 (4) | −0.0091 (4) |
N1 | 0.0250 (17) | 0.0215 (17) | 0.0250 (16) | −0.0035 (13) | 0.0139 (14) | −0.0051 (12) |
N2 | 0.0225 (16) | 0.0189 (15) | 0.0208 (15) | −0.0023 (13) | 0.0094 (13) | −0.0026 (12) |
N3 | 0.0319 (18) | 0.0209 (16) | 0.0296 (17) | −0.0010 (14) | 0.0163 (15) | −0.0004 (13) |
O1 | 0.0219 (14) | 0.0301 (14) | 0.0279 (14) | −0.0075 (12) | 0.0078 (12) | −0.0071 (11) |
O2 | 0.0340 (17) | 0.0457 (17) | 0.062 (2) | 0.0014 (15) | 0.0293 (16) | −0.0103 (15) |
O3 | 0.0351 (16) | 0.0432 (17) | 0.0282 (15) | −0.0079 (14) | 0.0040 (13) | −0.0083 (13) |
O4 | 0.0288 (15) | 0.0266 (14) | 0.0359 (15) | 0.0049 (12) | 0.0184 (13) | 0.0102 (12) |
O5 | 0.0332 (15) | 0.0243 (14) | 0.0272 (14) | −0.0045 (12) | 0.0034 (12) | 0.0117 (12) |
O6 | 0.0239 (13) | 0.0237 (13) | 0.0213 (13) | −0.0053 (12) | 0.0082 (11) | 0.0029 (10) |
O7 | 0.0278 (16) | 0.0509 (18) | 0.0326 (16) | −0.0123 (14) | 0.0001 (13) | 0.0229 (13) |
C1 | 0.037 (2) | 0.046 (3) | 0.037 (2) | −0.013 (2) | 0.026 (2) | −0.017 (2) |
C2 | 0.045 (3) | 0.044 (3) | 0.047 (3) | −0.019 (2) | 0.024 (2) | −0.023 (2) |
C3 | 0.050 (3) | 0.045 (3) | 0.047 (3) | −0.028 (2) | 0.025 (2) | −0.017 (2) |
C4 | 0.045 (3) | 0.047 (3) | 0.038 (2) | −0.023 (2) | 0.028 (2) | −0.016 (2) |
C5 | 0.0203 (19) | 0.0192 (19) | 0.0242 (19) | −0.0032 (15) | 0.0086 (16) | −0.0037 (14) |
C6 | 0.0206 (19) | 0.0227 (18) | 0.0212 (18) | −0.0019 (16) | 0.0088 (16) | −0.0029 (15) |
C7 | 0.033 (2) | 0.026 (2) | 0.034 (2) | −0.0088 (18) | 0.0199 (19) | −0.0069 (17) |
C8 | 0.033 (2) | 0.029 (2) | 0.027 (2) | −0.0013 (18) | 0.0179 (18) | −0.0038 (16) |
C9 | 0.028 (2) | 0.027 (2) | 0.027 (2) | −0.0075 (17) | 0.0125 (17) | −0.0092 (16) |
C10 | 0.0183 (18) | 0.0230 (19) | 0.0235 (19) | 0.0013 (16) | 0.0076 (16) | −0.0044 (15) |
C11 | 0.024 (2) | 0.0212 (19) | 0.0224 (19) | −0.0003 (16) | 0.0081 (16) | 0.0018 (15) |
C12 | 0.057 (3) | 0.026 (2) | 0.043 (3) | −0.011 (2) | 0.028 (2) | −0.0108 (19) |
C13 | 0.104 (5) | 0.031 (3) | 0.068 (4) | −0.021 (3) | 0.054 (3) | −0.019 (2) |
C14 | 0.097 (4) | 0.024 (3) | 0.080 (4) | −0.016 (3) | 0.057 (4) | −0.001 (2) |
C15 | 0.064 (3) | 0.026 (2) | 0.050 (3) | −0.003 (2) | 0.038 (3) | 0.001 (2) |
C16 | 0.038 (2) | 0.035 (2) | 0.029 (2) | −0.0086 (19) | 0.0201 (19) | −0.0066 (18) |
C17 | 0.080 (4) | 0.030 (2) | 0.050 (3) | −0.015 (2) | 0.044 (3) | −0.007 (2) |
C18 | 0.103 (5) | 0.039 (3) | 0.056 (3) | −0.017 (3) | 0.052 (3) | −0.003 (2) |
C19 | 0.080 (4) | 0.056 (3) | 0.047 (3) | −0.018 (3) | 0.045 (3) | −0.005 (2) |
C20 | 0.047 (3) | 0.048 (3) | 0.039 (2) | −0.012 (2) | 0.031 (2) | −0.015 (2) |
C21 | 0.029 (2) | 0.034 (2) | 0.032 (2) | −0.0122 (18) | 0.0185 (18) | −0.0106 (17) |
C22 | 0.028 (2) | 0.0195 (19) | 0.0191 (18) | −0.0038 (17) | 0.0076 (16) | 0.0018 (15) |
C23 | 0.034 (2) | 0.044 (3) | 0.042 (2) | 0.008 (2) | 0.021 (2) | 0.024 (2) |
C24 | 0.030 (2) | 0.036 (2) | 0.035 (2) | 0.0013 (19) | 0.0116 (19) | 0.0179 (18) |
C25 | 0.029 (2) | 0.031 (2) | 0.037 (2) | 0.0028 (18) | 0.0144 (19) | 0.0160 (18) |
C26 | 0.027 (2) | 0.026 (2) | 0.0174 (18) | −0.0004 (17) | 0.0073 (17) | 0.0040 (15) |
Geometric parameters (Å, º) top
Eu1—O1i | 2.365 (2) | C6—C7 | 1.380 (5) |
Eu1—O5ii | 2.379 (2) | C7—C8 | 1.401 (5) |
Eu1—O7iii | 2.387 (3) | C7—H7 | 0.9300 |
Eu1—O6iv | 2.391 (2) | C8—C9 | 1.381 (5) |
Eu1—O4 | 2.430 (2) | C8—C16 | 1.486 (5) |
Eu1—N2 | 2.572 (3) | C9—C10 | 1.382 (5) |
Eu1—N1 | 2.597 (3) | C9—H9 | 0.9300 |
Eu1—N3 | 2.652 (3) | C10—C11 | 1.485 (5) |
Eu1—O5 | 2.715 (3) | C11—C12 | 1.381 (5) |
Eu1—Eu1ii | 4.0961 (4) | C12—C13 | 1.373 (6) |
S1—O3 | 1.435 (3) | C12—H12 | 0.9300 |
S1—O2 | 1.444 (3) | C13—C14 | 1.360 (6) |
S1—O1 | 1.474 (3) | C13—H13 | 0.9300 |
S1—C21 | 1.798 (4) | C14—C15 | 1.379 (6) |
N1—C1 | 1.329 (5) | C14—H14 | 0.9300 |
N1—C5 | 1.338 (4) | C15—H15 | 0.9300 |
N2—C10 | 1.351 (4) | C16—C17 | 1.386 (6) |
N2—C6 | 1.352 (4) | C16—C21 | 1.417 (5) |
N3—C11 | 1.346 (4) | C17—C18 | 1.394 (6) |
N3—C15 | 1.348 (5) | C17—H17 | 0.9300 |
O1—Eu1iii | 2.365 (2) | C18—C19 | 1.360 (6) |
O4—C22 | 1.249 (4) | C18—H18 | 0.9300 |
O5—C22 | 1.272 (4) | C19—C20 | 1.380 (6) |
O5—Eu1ii | 2.379 (2) | C19—H19 | 0.9300 |
O6—C26 | 1.259 (4) | C20—C21 | 1.385 (5) |
O6—Eu1v | 2.391 (2) | C20—H20 | 0.9300 |
O7—C26 | 1.255 (4) | C22—C23 | 1.498 (5) |
O7—Eu1i | 2.387 (3) | C23—C24 | 1.501 (5) |
C1—C2 | 1.379 (5) | C23—H23A | 0.9700 |
C1—H1 | 0.9300 | C23—H23B | 0.9700 |
C2—C3 | 1.363 (6) | C24—C25 | 1.510 (5) |
C2—H2 | 0.9300 | C24—H24A | 0.9700 |
C3—C4 | 1.376 (5) | C24—H24B | 0.9700 |
C3—H3 | 0.9300 | C25—C26 | 1.524 (5) |
C4—C5 | 1.388 (5) | C25—H25A | 0.9700 |
C4—H4 | 0.9300 | C25—H25B | 0.9700 |
C5—C6 | 1.483 (5) | | |
| | | |
O1i—Eu1—O5ii | 141.57 (9) | C3—C4—H4 | 120.4 |
O1i—Eu1—O7iii | 144.04 (9) | C5—C4—H4 | 120.4 |
O5ii—Eu1—O7iii | 72.06 (9) | N1—C5—C4 | 121.7 (3) |
O1i—Eu1—O6iv | 79.44 (8) | N1—C5—C6 | 116.7 (3) |
O5ii—Eu1—O6iv | 73.17 (8) | C4—C5—C6 | 121.6 (3) |
O7iii—Eu1—O6iv | 134.17 (8) | N2—C6—C7 | 122.2 (3) |
O1i—Eu1—O4 | 76.23 (9) | N2—C6—C5 | 115.3 (3) |
O5ii—Eu1—O4 | 121.24 (9) | C7—C6—C5 | 122.4 (3) |
O7iii—Eu1—O4 | 97.24 (10) | C6—C7—C8 | 120.1 (3) |
O6iv—Eu1—O4 | 76.51 (8) | C6—C7—H7 | 119.9 |
O1i—Eu1—N2 | 83.61 (9) | C8—C7—H7 | 119.9 |
O5ii—Eu1—N2 | 100.35 (9) | C9—C8—C7 | 116.8 (3) |
O7iii—Eu1—N2 | 75.68 (9) | C9—C8—C16 | 123.6 (3) |
O6iv—Eu1—N2 | 139.88 (9) | C7—C8—C16 | 119.5 (3) |
O4—Eu1—N2 | 133.69 (8) | C8—C9—C10 | 120.5 (3) |
O1i—Eu1—N1 | 74.16 (9) | C8—C9—H9 | 119.8 |
O5ii—Eu1—N1 | 74.25 (9) | C10—C9—H9 | 119.8 |
O7iii—Eu1—N1 | 118.83 (10) | N2—C10—C9 | 122.1 (3) |
O6iv—Eu1—N1 | 78.20 (9) | N2—C10—C11 | 116.2 (3) |
O4—Eu1—N1 | 143.92 (9) | C9—C10—C11 | 121.5 (3) |
N2—Eu1—N1 | 62.21 (9) | N3—C11—C12 | 122.4 (3) |
O1i—Eu1—N3 | 77.25 (9) | N3—C11—C10 | 116.2 (3) |
O5ii—Eu1—N3 | 138.24 (9) | C12—C11—C10 | 121.1 (3) |
O7iii—Eu1—N3 | 67.11 (9) | C13—C12—C11 | 119.0 (4) |
O6iv—Eu1—N3 | 145.36 (8) | C13—C12—H12 | 120.5 |
O4—Eu1—N3 | 73.30 (9) | C11—C12—H12 | 120.5 |
N2—Eu1—N3 | 61.68 (9) | C14—C13—C12 | 119.2 (4) |
N1—Eu1—N3 | 118.75 (9) | C14—C13—H13 | 120.4 |
O1i—Eu1—O5 | 122.88 (8) | C12—C13—H13 | 120.4 |
O5ii—Eu1—O5 | 73.15 (9) | C13—C14—C15 | 119.5 (4) |
O7iii—Eu1—O5 | 70.14 (9) | C13—C14—H14 | 120.2 |
O6iv—Eu1—O5 | 71.88 (8) | C15—C14—H14 | 120.2 |
O4—Eu1—O5 | 49.83 (8) | N3—C15—C14 | 122.2 (4) |
N2—Eu1—O5 | 145.58 (8) | N3—C15—H15 | 118.9 |
N1—Eu1—O5 | 140.72 (8) | C14—C15—H15 | 118.9 |
N3—Eu1—O5 | 100.19 (9) | C17—C16—C21 | 117.1 (4) |
O1i—Eu1—Eu1ii | 144.58 (6) | C17—C16—C8 | 117.2 (4) |
O5ii—Eu1—Eu1ii | 39.37 (6) | C21—C16—C8 | 125.7 (4) |
O7iii—Eu1—Eu1ii | 66.16 (6) | C16—C17—C18 | 122.5 (4) |
O6iv—Eu1—Eu1ii | 68.02 (6) | C16—C17—H17 | 118.8 |
O4—Eu1—Eu1ii | 82.75 (6) | C18—C17—H17 | 118.8 |
N2—Eu1—Eu1ii | 130.63 (6) | C19—C18—C17 | 119.8 (4) |
N1—Eu1—Eu1ii | 110.82 (6) | C19—C18—H18 | 120.1 |
N3—Eu1—Eu1ii | 123.40 (7) | C17—C18—H18 | 120.1 |
O5—Eu1—Eu1ii | 33.78 (5) | C18—C19—C20 | 119.2 (4) |
O3—S1—O2 | 115.07 (18) | C18—C19—H19 | 120.4 |
O3—S1—O1 | 111.16 (16) | C20—C19—H19 | 120.4 |
O2—S1—O1 | 112.07 (16) | C19—C20—C21 | 122.1 (4) |
O3—S1—C21 | 108.38 (17) | C19—C20—H20 | 118.9 |
O2—S1—C21 | 105.46 (18) | C21—C20—H20 | 118.9 |
O1—S1—C21 | 103.84 (17) | C20—C21—C16 | 119.3 (4) |
C1—N1—C5 | 117.6 (3) | C20—C21—S1 | 115.1 (3) |
C1—N1—Eu1 | 121.0 (2) | C16—C21—S1 | 125.6 (3) |
C5—N1—Eu1 | 121.4 (2) | O4—C22—O5 | 120.0 (3) |
C10—N2—C6 | 117.6 (3) | O4—C22—C23 | 120.3 (3) |
C10—N2—Eu1 | 118.9 (2) | O5—C22—C23 | 119.7 (3) |
C6—N2—Eu1 | 121.3 (2) | C22—C23—C24 | 114.1 (3) |
C11—N3—C15 | 117.7 (3) | C22—C23—H23A | 108.7 |
C11—N3—Eu1 | 117.6 (2) | C24—C23—H23A | 108.7 |
C15—N3—Eu1 | 123.7 (2) | C22—C23—H23B | 108.7 |
S1—O1—Eu1iii | 153.67 (15) | C24—C23—H23B | 108.7 |
C22—O4—Eu1 | 102.0 (2) | H23A—C23—H23B | 107.6 |
C22—O5—Eu1ii | 156.7 (2) | C23—C24—C25 | 115.5 (3) |
C22—O5—Eu1 | 87.9 (2) | C23—C24—H24A | 108.4 |
Eu1ii—O5—Eu1 | 106.85 (9) | C25—C24—H24A | 108.4 |
C26—O6—Eu1v | 135.8 (2) | C23—C24—H24B | 108.4 |
C26—O7—Eu1i | 139.5 (2) | C25—C24—H24B | 108.4 |
N1—C1—C2 | 124.0 (4) | H24A—C24—H24B | 107.5 |
N1—C1—H1 | 118.0 | C24—C25—C26 | 114.1 (3) |
C2—C1—H1 | 118.0 | C24—C25—H25A | 108.7 |
C3—C2—C1 | 118.0 (4) | C26—C25—H25A | 108.7 |
C3—C2—H2 | 121.0 | C24—C25—H25B | 108.7 |
C1—C2—H2 | 121.0 | C26—C25—H25B | 108.7 |
C2—C3—C4 | 119.3 (4) | H25A—C25—H25B | 107.6 |
C2—C3—H3 | 120.4 | O7—C26—O6 | 125.7 (3) |
C4—C3—H3 | 120.4 | O7—C26—C25 | 116.6 (3) |
C3—C4—C5 | 119.3 (4) | O6—C26—C25 | 117.6 (3) |
| | | |
O3—S1—O1—Eu1iii | −161.9 (3) | C10—C11—C12—C13 | 173.7 (4) |
O2—S1—O1—Eu1iii | −31.5 (4) | C11—C12—C13—C14 | −2.1 (8) |
C21—S1—O1—Eu1iii | 81.8 (4) | C12—C13—C14—C15 | 3.0 (9) |
C5—N1—C1—C2 | 1.8 (6) | C11—N3—C15—C14 | −0.2 (7) |
Eu1—N1—C1—C2 | −177.4 (3) | Eu1—N3—C15—C14 | 167.6 (4) |
N1—C1—C2—C3 | −0.8 (7) | C13—C14—C15—N3 | −1.9 (9) |
C1—C2—C3—C4 | 0.0 (7) | C9—C8—C16—C17 | 141.5 (4) |
C2—C3—C4—C5 | −0.3 (7) | C7—C8—C16—C17 | −36.8 (6) |
C1—N1—C5—C4 | −2.1 (6) | C9—C8—C16—C21 | −38.5 (6) |
Eu1—N1—C5—C4 | 177.2 (3) | C7—C8—C16—C21 | 143.2 (4) |
C1—N1—C5—C6 | 176.6 (3) | C21—C16—C17—C18 | 2.8 (7) |
Eu1—N1—C5—C6 | −4.1 (4) | C8—C16—C17—C18 | −177.2 (5) |
C3—C4—C5—N1 | 1.3 (7) | C16—C17—C18—C19 | −0.2 (8) |
C3—C4—C5—C6 | −177.3 (4) | C17—C18—C19—C20 | −2.0 (9) |
C10—N2—C6—C7 | 1.1 (5) | C18—C19—C20—C21 | 1.5 (8) |
Eu1—N2—C6—C7 | −162.2 (3) | C19—C20—C21—C16 | 1.2 (7) |
C10—N2—C6—C5 | −176.4 (3) | C19—C20—C21—S1 | −179.9 (4) |
Eu1—N2—C6—C5 | 20.2 (4) | C17—C16—C21—C20 | −3.2 (6) |
N1—C5—C6—N2 | −10.2 (5) | C8—C16—C21—C20 | 176.8 (4) |
C4—C5—C6—N2 | 168.5 (4) | C17—C16—C21—S1 | 178.0 (3) |
N1—C5—C6—C7 | 172.3 (3) | C8—C16—C21—S1 | −1.9 (6) |
C4—C5—C6—C7 | −9.0 (6) | O3—S1—C21—C20 | 144.9 (3) |
N2—C6—C7—C8 | 4.5 (6) | O2—S1—C21—C20 | 21.1 (4) |
C5—C6—C7—C8 | −178.1 (4) | O1—S1—C21—C20 | −96.9 (3) |
C6—C7—C8—C9 | −3.9 (6) | O3—S1—C21—C16 | −36.3 (4) |
C6—C7—C8—C16 | 174.5 (4) | O2—S1—C21—C16 | −160.0 (4) |
C7—C8—C9—C10 | −2.1 (6) | O1—S1—C21—C16 | 82.0 (4) |
C16—C8—C9—C10 | 179.5 (4) | Eu1—O4—C22—O5 | 6.1 (4) |
C6—N2—C10—C9 | −7.4 (5) | Eu1—O4—C22—C23 | −174.6 (3) |
Eu1—N2—C10—C9 | 156.4 (3) | Eu1ii—O5—C22—O4 | −135.7 (5) |
C6—N2—C10—C11 | 167.4 (3) | Eu1—O5—C22—O4 | −5.4 (3) |
Eu1—N2—C10—C11 | −28.8 (4) | Eu1ii—O5—C22—C23 | 45.1 (8) |
C8—C9—C10—N2 | 8.1 (6) | Eu1—O5—C22—C23 | 175.4 (3) |
C8—C9—C10—C11 | −166.5 (3) | O4—C22—C23—C24 | −5.7 (6) |
C15—N3—C11—C12 | 1.1 (6) | O5—C22—C23—C24 | 173.6 (3) |
Eu1—N3—C11—C12 | −167.5 (3) | C22—C23—C24—C25 | 177.5 (4) |
C15—N3—C11—C10 | −172.9 (3) | C23—C24—C25—C26 | −172.5 (4) |
Eu1—N3—C11—C10 | 18.6 (4) | Eu1i—O7—C26—O6 | −29.2 (7) |
N2—C10—C11—N3 | 5.9 (5) | Eu1i—O7—C26—C25 | 148.5 (3) |
C9—C10—C11—N3 | −179.2 (3) | Eu1v—O6—C26—O7 | 28.9 (6) |
N2—C10—C11—C12 | −168.1 (4) | Eu1v—O6—C26—C25 | −148.8 (3) |
C9—C10—C11—C12 | 6.7 (6) | C24—C25—C26—O7 | 37.6 (5) |
N3—C11—C12—C13 | 0.0 (7) | C24—C25—C26—O6 | −144.6 (4) |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x, −y+1/2, z−1/2; (iv) −x+1, y+1/2, −z+3/2; (v) −x+1, y−1/2, −z+3/2. |
Crystal data top
C67H58Er4N6O30S2 | F(000) = 4184 |
Mr = 2160.35 | Dx = 2.010 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 39.336 (4) Å | Cell parameters from 3921 reflections |
b = 8.6380 (9) Å | θ = 2.4–25.9° |
c = 25.594 (3) Å | µ = 4.81 mm−1 |
β = 124.837 (2)° | T = 296 K |
V = 7137.9 (13) Å3 | Block, pink |
Z = 4 | 0.14 × 0.10 × 0.08 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 5082 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.039 |
Absorption correction: multi-scan sadabs | θmax = 25.1°, θmin = 2.4° |
Tmin = 0.565, Tmax = 0.682 | h = −46→38 |
17352 measured reflections | k = −10→10 |
6309 independent reflections | l = −19→30 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H-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 reflections | Δρmax = 0.93 e Å−3 |
492 parameters | Δρmin = −0.79 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Er1 | 0.13567 (2) | 0.45805 (3) | 0.28112 (2) | 0.02142 (7) | |
Er2 | 0.03409 (2) | 0.44330 (3) | 0.08917 (2) | 0.02384 (8) | |
S1 | 0.25395 (4) | 0.11417 (17) | 0.61042 (7) | 0.0341 (4) | |
N1 | 0.17043 (13) | 0.6892 (5) | 0.3490 (2) | 0.0277 (11) | |
N2 | 0.15565 (12) | 0.4299 (5) | 0.3911 (2) | 0.0265 (10) | |
N3 | 0.11122 (13) | 0.2171 (5) | 0.3018 (2) | 0.0296 (11) | |
O1 | 0.29640 (11) | 0.0957 (5) | 0.66815 (17) | 0.0402 (10) | |
O2 | 0.22943 (14) | −0.0204 (5) | 0.5986 (3) | 0.0730 (17) | |
O3 | 0.25373 (14) | 0.1681 (6) | 0.5572 (2) | 0.0622 (14) | |
O4 | 0.12974 (12) | 0.6221 (4) | 0.20973 (18) | 0.0393 (10) | |
O5 | 0.08189 (12) | 0.6182 (5) | 0.10559 (18) | 0.0409 (10) | |
O6 | 0.13844 (12) | 1.2844 (4) | 0.21811 (18) | 0.0385 (10) | |
O7 | 0.08943 (11) | 1.2988 (4) | 0.11442 (18) | 0.0395 (10) | |
O8 | 0.01226 (12) | 0.6829 (4) | 0.10906 (17) | 0.0428 (11) | |
O9 | −0.01047 (11) | 0.6339 (4) | 0.01072 (16) | 0.0344 (9) | |
O10 | 0.01510 (11) | 1.1916 (4) | 0.09701 (19) | 0.0388 (10) | |
O11 | −0.03144 (11) | 1.3740 (4) | 0.06336 (19) | 0.0410 (10) | |
O12 | 0.06100 (11) | 0.4395 (4) | 0.19521 (17) | 0.0326 (9) | |
O13 | 0.08085 (12) | 0.5644 (4) | 0.28229 (19) | 0.0415 (11) | |
C1 | 0.17766 (17) | 0.8157 (6) | 0.3261 (3) | 0.0378 (15) | |
H1 | 0.1699 | 0.8143 | 0.2843 | 0.045* | |
C2 | 0.19627 (19) | 0.9483 (7) | 0.3622 (3) | 0.0456 (17) | |
H2 | 0.2004 | 1.0342 | 0.3445 | 0.055* | |
C3 | 0.20845 (17) | 0.9507 (7) | 0.4242 (3) | 0.0386 (15) | |
H3 | 0.2211 | 1.0377 | 0.4495 | 0.046* | |
C4 | 0.20142 (16) | 0.8192 (6) | 0.4481 (3) | 0.0335 (14) | |
H4 | 0.2089 | 0.8184 | 0.4898 | 0.040* | |
C5 | 0.18322 (15) | 0.6893 (6) | 0.4101 (2) | 0.0284 (13) | |
C6 | 0.17631 (16) | 0.5432 (6) | 0.4336 (2) | 0.0268 (12) | |
C7 | 0.19161 (17) | 0.5256 (6) | 0.4980 (3) | 0.0312 (13) | |
H7 | 0.2048 | 0.6079 | 0.5260 | 0.037* | |
C8 | 0.18704 (15) | 0.3864 (6) | 0.5195 (2) | 0.0269 (12) | |
C9 | 0.16536 (15) | 0.2696 (6) | 0.4750 (2) | 0.0296 (13) | |
H9 | 0.1616 | 0.1743 | 0.4879 | 0.036* | |
C10 | 0.14940 (15) | 0.2953 (6) | 0.4115 (2) | 0.0257 (12) | |
C11 | 0.12420 (15) | 0.1783 (6) | 0.3621 (2) | 0.0271 (12) | |
C12 | 0.11342 (17) | 0.0363 (6) | 0.3751 (3) | 0.0322 (13) | |
H12 | 0.1225 | 0.0112 | 0.4165 | 0.039* | |
C13 | 0.08924 (18) | −0.0662 (6) | 0.3260 (3) | 0.0383 (15) | |
H13 | 0.0821 | −0.1614 | 0.3341 | 0.046* | |
C14 | 0.07575 (19) | −0.0265 (7) | 0.2649 (3) | 0.0417 (16) | |
H14 | 0.0594 | −0.0939 | 0.2311 | 0.050* | |
C15 | 0.08704 (17) | 0.1155 (7) | 0.2551 (3) | 0.0379 (15) | |
H15 | 0.0773 | 0.1429 | 0.2136 | 0.046* | |
C16 | 0.20392 (16) | 0.3728 (6) | 0.5892 (2) | 0.0286 (13) | |
C17 | 0.18963 (19) | 0.4820 (7) | 0.6117 (3) | 0.0422 (16) | |
H17 | 0.1702 | 0.5544 | 0.5837 | 0.051* | |
C18 | 0.20376 (18) | 0.4856 (7) | 0.6751 (3) | 0.0424 (16) | |
H18 | 0.1933 | 0.5590 | 0.6890 | 0.051* | |
C19 | 0.23311 (18) | 0.3818 (7) | 0.7177 (3) | 0.0423 (16) | |
H19 | 0.2429 | 0.3848 | 0.7605 | 0.051* | |
C20 | 0.24754 (17) | 0.2740 (7) | 0.6959 (3) | 0.0356 (14) | |
H20 | 0.2679 | 0.2053 | 0.7248 | 0.043* | |
C21 | 0.23289 (15) | 0.2630 (6) | 0.6321 (2) | 0.0248 (12) | |
C22 | 0.11389 (17) | 0.6720 (6) | 0.1533 (3) | 0.0298 (13) | |
C23 | 0.13497 (18) | 0.8067 (6) | 0.1456 (3) | 0.0354 (14) | |
H23A | 0.1310 | 0.8011 | 0.1046 | 0.042* | |
H23B | 0.1645 | 0.8042 | 0.1787 | 0.042* | |
C24 | 0.11627 (18) | 0.9551 (6) | 0.1504 (3) | 0.0372 (15) | |
H24A | 0.1171 | 0.9529 | 0.1890 | 0.045* | |
H24B | 0.0875 | 0.9613 | 0.1145 | 0.045* | |
C25 | 0.13929 (17) | 1.0993 (6) | 0.1510 (3) | 0.0331 (14) | |
H25A | 0.1686 | 1.0906 | 0.1846 | 0.040* | |
H25B | 0.1362 | 1.1088 | 0.1107 | 0.040* | |
C26 | 0.12153 (16) | 1.2389 (6) | 0.1619 (3) | 0.0258 (12) | |
C27 | −0.00833 (16) | 0.7252 (6) | 0.0524 (3) | 0.0306 (13) | |
C28 | −0.02864 (18) | 0.8809 (6) | 0.0335 (3) | 0.0360 (14) | |
H28A | −0.0546 | 0.8724 | −0.0082 | 0.043* | |
H28B | −0.0110 | 0.9518 | 0.0298 | 0.043* | |
C29 | −0.03737 (19) | 0.9490 (6) | 0.0794 (3) | 0.0399 (15) | |
H29A | −0.0121 | 0.9469 | 0.1221 | 0.048* | |
H29B | −0.0577 | 0.8852 | 0.0791 | 0.048* | |
C30 | −0.05337 (18) | 1.1155 (6) | 0.0626 (3) | 0.0448 (16) | |
H30A | −0.0762 | 1.1196 | 0.0179 | 0.054* | |
H30B | −0.0641 | 1.1443 | 0.0871 | 0.054* | |
C31 | −0.02105 (18) | 1.2326 (7) | 0.0748 (3) | 0.0343 (14) | |
C32 | 0.05229 (19) | 0.5087 (7) | 0.2308 (3) | 0.0394 (15) | |
C33 | 0.0083 (2) | 0.5060 (14) | 0.2105 (4) | 0.109 (4) | |
H33A | 0.0011 | 0.4007 | 0.2136 | 0.130* | |
H33B | −0.0095 | 0.5369 | 0.1662 | 0.130* | |
C34 | 0.0000 | 0.6119 (17) | 0.2500 | 0.145 (7) | |
H34A | 0.0238 | 0.6774 | 0.2777 | 0.174* | 0.5 |
H34B | −0.0238 | 0.6774 | 0.2223 | 0.174* | 0.5 |
O14 | 0.14412 (15) | 0.8849 (6) | 0.5144 (2) | 0.0802 (16) | |
O15 | 0.90320 (16) | 0.6006 (7) | 0.9995 (4) | 0.123 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Er1 | 0.02235 (13) | 0.02192 (13) | 0.01507 (13) | 0.00158 (10) | 0.00778 (11) | 0.00118 (10) |
Er2 | 0.02549 (14) | 0.02409 (13) | 0.01544 (13) | 0.00013 (10) | 0.00786 (11) | 0.00048 (10) |
S1 | 0.0281 (8) | 0.0377 (8) | 0.0263 (8) | 0.0060 (7) | 0.0096 (7) | −0.0031 (7) |
N1 | 0.031 (3) | 0.024 (2) | 0.024 (3) | 0.000 (2) | 0.013 (2) | 0.002 (2) |
N2 | 0.020 (2) | 0.032 (3) | 0.022 (2) | −0.0001 (19) | 0.008 (2) | −0.006 (2) |
N3 | 0.033 (3) | 0.027 (2) | 0.020 (2) | −0.001 (2) | 0.010 (2) | −0.001 (2) |
O1 | 0.027 (2) | 0.056 (3) | 0.025 (2) | 0.0107 (19) | 0.0078 (18) | −0.0001 (19) |
O2 | 0.050 (3) | 0.041 (3) | 0.106 (5) | −0.011 (2) | 0.032 (3) | −0.025 (3) |
O3 | 0.067 (3) | 0.096 (4) | 0.036 (3) | 0.039 (3) | 0.036 (3) | 0.015 (3) |
O4 | 0.049 (3) | 0.036 (2) | 0.030 (2) | −0.004 (2) | 0.021 (2) | 0.0067 (19) |
O5 | 0.036 (2) | 0.043 (2) | 0.031 (2) | −0.006 (2) | 0.012 (2) | 0.004 (2) |
O6 | 0.044 (2) | 0.038 (2) | 0.032 (2) | 0.0068 (19) | 0.020 (2) | −0.0025 (19) |
O7 | 0.037 (2) | 0.044 (2) | 0.030 (2) | 0.0096 (19) | 0.014 (2) | 0.0007 (19) |
O8 | 0.053 (3) | 0.042 (2) | 0.019 (2) | 0.011 (2) | 0.012 (2) | −0.0006 (18) |
O9 | 0.043 (2) | 0.032 (2) | 0.021 (2) | 0.0002 (19) | 0.0143 (19) | −0.0040 (17) |
O10 | 0.032 (2) | 0.036 (2) | 0.044 (3) | −0.0016 (18) | 0.018 (2) | 0.0020 (19) |
O11 | 0.042 (2) | 0.028 (2) | 0.051 (3) | 0.0029 (19) | 0.026 (2) | 0.004 (2) |
O12 | 0.034 (2) | 0.040 (2) | 0.023 (2) | −0.0003 (18) | 0.0160 (19) | 0.0012 (18) |
O13 | 0.030 (2) | 0.052 (3) | 0.033 (2) | 0.0033 (19) | 0.013 (2) | −0.010 (2) |
C1 | 0.043 (4) | 0.038 (4) | 0.028 (3) | −0.005 (3) | 0.018 (3) | 0.001 (3) |
C2 | 0.044 (4) | 0.037 (4) | 0.046 (4) | −0.010 (3) | 0.020 (3) | −0.001 (3) |
C3 | 0.033 (3) | 0.038 (4) | 0.041 (4) | −0.005 (3) | 0.018 (3) | −0.013 (3) |
C4 | 0.036 (3) | 0.029 (3) | 0.030 (3) | 0.002 (3) | 0.015 (3) | −0.005 (3) |
C5 | 0.025 (3) | 0.030 (3) | 0.021 (3) | 0.001 (2) | 0.007 (3) | −0.001 (2) |
C6 | 0.029 (3) | 0.028 (3) | 0.021 (3) | 0.004 (2) | 0.013 (3) | 0.001 (2) |
C7 | 0.032 (3) | 0.036 (3) | 0.024 (3) | 0.007 (3) | 0.015 (3) | −0.003 (3) |
C8 | 0.025 (3) | 0.031 (3) | 0.021 (3) | 0.007 (2) | 0.011 (3) | 0.004 (2) |
C9 | 0.030 (3) | 0.030 (3) | 0.025 (3) | 0.003 (2) | 0.013 (3) | 0.003 (2) |
C10 | 0.022 (3) | 0.027 (3) | 0.021 (3) | 0.007 (2) | 0.008 (2) | 0.002 (2) |
C11 | 0.023 (3) | 0.033 (3) | 0.023 (3) | 0.000 (2) | 0.011 (3) | −0.001 (2) |
C12 | 0.036 (3) | 0.036 (3) | 0.030 (3) | −0.001 (3) | 0.022 (3) | 0.004 (3) |
C13 | 0.046 (4) | 0.032 (3) | 0.040 (4) | −0.009 (3) | 0.027 (3) | −0.003 (3) |
C14 | 0.046 (4) | 0.034 (3) | 0.040 (4) | −0.014 (3) | 0.021 (3) | −0.009 (3) |
C15 | 0.037 (3) | 0.043 (4) | 0.029 (3) | −0.004 (3) | 0.017 (3) | −0.003 (3) |
C16 | 0.028 (3) | 0.032 (3) | 0.025 (3) | 0.003 (2) | 0.014 (3) | −0.003 (2) |
C17 | 0.047 (4) | 0.043 (4) | 0.030 (3) | 0.014 (3) | 0.018 (3) | −0.002 (3) |
C18 | 0.044 (4) | 0.048 (4) | 0.033 (4) | 0.005 (3) | 0.020 (3) | −0.013 (3) |
C19 | 0.041 (4) | 0.060 (4) | 0.022 (3) | 0.000 (3) | 0.015 (3) | −0.004 (3) |
C20 | 0.034 (3) | 0.039 (3) | 0.022 (3) | 0.004 (3) | 0.009 (3) | 0.002 (3) |
C21 | 0.024 (3) | 0.029 (3) | 0.020 (3) | 0.003 (2) | 0.012 (2) | 0.004 (2) |
C22 | 0.035 (3) | 0.028 (3) | 0.030 (3) | 0.002 (3) | 0.021 (3) | 0.001 (3) |
C23 | 0.041 (4) | 0.033 (3) | 0.043 (4) | −0.004 (3) | 0.031 (3) | 0.001 (3) |
C24 | 0.048 (4) | 0.025 (3) | 0.043 (4) | 0.004 (3) | 0.028 (3) | 0.004 (3) |
C25 | 0.036 (3) | 0.027 (3) | 0.035 (3) | 0.000 (3) | 0.020 (3) | 0.001 (3) |
C26 | 0.032 (3) | 0.023 (3) | 0.025 (3) | −0.010 (2) | 0.017 (3) | −0.002 (2) |
C27 | 0.031 (3) | 0.034 (3) | 0.023 (3) | −0.010 (3) | 0.013 (3) | −0.003 (3) |
C28 | 0.039 (3) | 0.033 (3) | 0.024 (3) | 0.004 (3) | 0.011 (3) | −0.002 (3) |
C29 | 0.045 (4) | 0.033 (3) | 0.051 (4) | −0.004 (3) | 0.033 (3) | −0.003 (3) |
C30 | 0.044 (4) | 0.037 (4) | 0.064 (5) | −0.001 (3) | 0.037 (4) | −0.007 (3) |
C31 | 0.041 (4) | 0.033 (3) | 0.027 (3) | −0.003 (3) | 0.018 (3) | −0.004 (3) |
C32 | 0.035 (4) | 0.051 (4) | 0.030 (4) | 0.007 (3) | 0.018 (3) | 0.007 (3) |
C33 | 0.040 (5) | 0.249 (13) | 0.038 (5) | −0.003 (6) | 0.023 (4) | −0.037 (6) |
C34 | 0.072 (10) | 0.094 (11) | 0.23 (2) | 0.000 | 0.065 (13) | 0.000 |
O14 | 0.070 (3) | 0.099 (4) | 0.070 (4) | 0.008 (3) | 0.039 (3) | 0.030 (3) |
O15 | 0.055 (4) | 0.102 (5) | 0.178 (7) | −0.001 (3) | 0.046 (4) | −0.013 (5) |
Geometric parameters (Å, º) top
Er1—O4 | 2.217 (4) | C7—C8 | 1.377 (7) |
Er1—O6i | 2.250 (4) | C7—H7 | 0.9300 |
Er1—O1ii | 2.254 (4) | C8—C9 | 1.391 (7) |
Er1—O13 | 2.359 (4) | C8—C16 | 1.510 (7) |
Er1—N2 | 2.463 (4) | C9—C10 | 1.386 (7) |
Er1—O12 | 2.472 (4) | C9—H9 | 0.9300 |
Er1—N3 | 2.473 (4) | C10—C11 | 1.473 (7) |
Er1—N1 | 2.482 (4) | C11—C12 | 1.399 (7) |
Er2—O5 | 2.256 (4) | C12—C13 | 1.379 (7) |
Er2—O7i | 2.260 (4) | C12—H12 | 0.9300 |
Er2—O9iii | 2.265 (4) | C13—C14 | 1.377 (8) |
Er2—O12 | 2.282 (4) | C13—H13 | 0.9300 |
Er2—O11i | 2.344 (4) | C14—C15 | 1.376 (8) |
Er2—O10i | 2.345 (4) | C14—H14 | 0.9300 |
Er2—O8 | 2.404 (4) | C15—H15 | 0.9300 |
Er2—O9 | 2.407 (4) | C16—C17 | 1.380 (7) |
Er2—C31i | 2.691 (6) | C16—C21 | 1.405 (7) |
Er2—Er2iii | 3.8731 (6) | C17—C18 | 1.385 (8) |
S1—O2 | 1.428 (5) | C17—H17 | 0.9300 |
S1—O3 | 1.435 (4) | C18—C19 | 1.374 (8) |
S1—O1 | 1.476 (4) | C18—H18 | 0.9300 |
S1—C21 | 1.781 (5) | C19—C20 | 1.365 (8) |
N1—C5 | 1.340 (6) | C19—H19 | 0.9300 |
N1—C1 | 1.345 (6) | C20—C21 | 1.391 (7) |
N2—C6 | 1.339 (6) | C20—H20 | 0.9300 |
N2—C10 | 1.353 (6) | C22—C23 | 1.506 (7) |
N3—C15 | 1.343 (6) | C23—C24 | 1.517 (7) |
N3—C11 | 1.362 (6) | C23—H23A | 0.9700 |
O1—Er1ii | 2.254 (4) | C23—H23B | 0.9700 |
O4—C22 | 1.277 (6) | C24—C25 | 1.535 (7) |
O5—C22 | 1.240 (6) | C24—H24A | 0.9700 |
O6—C26 | 1.254 (6) | C24—H24B | 0.9700 |
O6—Er1iv | 2.250 (4) | C25—C26 | 1.497 (7) |
O7—C26 | 1.259 (6) | C25—H25A | 0.9700 |
O7—Er2iv | 2.260 (4) | C25—H25B | 0.9700 |
O8—C27 | 1.245 (6) | C27—C28 | 1.496 (7) |
O9—C27 | 1.290 (6) | C28—C29 | 1.519 (8) |
O9—Er2iii | 2.265 (4) | C28—H28A | 0.9700 |
O10—C31 | 1.244 (6) | C28—H28B | 0.9700 |
O10—Er2iv | 2.345 (4) | C29—C30 | 1.529 (7) |
O11—C31 | 1.268 (6) | C29—H29A | 0.9700 |
O11—Er2iv | 2.344 (4) | C29—H29B | 0.9700 |
O12—C32 | 1.288 (7) | C30—C31 | 1.511 (7) |
O13—C32 | 1.241 (7) | C30—H30A | 0.9700 |
C1—C2 | 1.388 (8) | C30—H30B | 0.9700 |
C1—H1 | 0.9300 | C31—Er2iv | 2.691 (6) |
C2—C3 | 1.371 (8) | C32—C33 | 1.494 (9) |
C2—H2 | 0.9300 | C33—C34 | 1.532 (11) |
C3—C4 | 1.391 (8) | C33—H33A | 0.9700 |
C3—H3 | 0.9300 | C33—H33B | 0.9700 |
C4—C5 | 1.387 (7) | C34—C33v | 1.532 (11) |
C4—H4 | 0.9300 | C34—H34A | 0.9700 |
C5—C6 | 1.489 (7) | C34—H34B | 0.9700 |
C6—C7 | 1.402 (7) | | |
| | | |
O4—Er1—O6i | 82.00 (14) | N1—C5—C6 | 115.9 (5) |
O4—Er1—O1ii | 97.95 (14) | C4—C5—C6 | 122.8 (5) |
O6i—Er1—O1ii | 75.44 (14) | N2—C6—C7 | 122.0 (5) |
O4—Er1—O13 | 95.45 (14) | N2—C6—C5 | 117.2 (5) |
O6i—Er1—O13 | 133.42 (13) | C7—C6—C5 | 120.8 (5) |
O1ii—Er1—O13 | 149.81 (13) | C8—C7—C6 | 119.9 (5) |
O4—Er1—N2 | 145.02 (14) | C8—C7—H7 | 120.0 |
O6i—Er1—N2 | 129.66 (14) | C6—C7—H7 | 120.0 |
O1ii—Er1—N2 | 79.74 (14) | C7—C8—C9 | 117.6 (5) |
O13—Er1—N2 | 73.84 (14) | C7—C8—C16 | 118.1 (5) |
O4—Er1—O12 | 78.24 (13) | C9—C8—C16 | 124.1 (5) |
O6i—Er1—O12 | 80.72 (13) | C10—C9—C8 | 120.0 (5) |
O1ii—Er1—O12 | 156.16 (13) | C10—C9—H9 | 120.0 |
O13—Er1—O12 | 53.59 (13) | C8—C9—H9 | 120.0 |
N2—Er1—O12 | 116.83 (13) | N2—C10—C9 | 122.0 (5) |
O4—Er1—N3 | 147.50 (14) | N2—C10—C11 | 116.1 (5) |
O6i—Er1—N3 | 77.05 (14) | C9—C10—C11 | 121.9 (5) |
O1ii—Er1—N3 | 100.45 (14) | N3—C11—C12 | 121.1 (5) |
O13—Er1—N3 | 81.68 (14) | N3—C11—C10 | 115.9 (5) |
N2—Er1—N3 | 65.30 (14) | C12—C11—C10 | 123.0 (5) |
O12—Er1—N3 | 74.10 (12) | C13—C12—C11 | 119.4 (5) |
O4—Er1—N1 | 79.58 (14) | C13—C12—H12 | 120.3 |
O6i—Er1—N1 | 143.61 (14) | C11—C12—H12 | 120.3 |
O1ii—Er1—N1 | 76.38 (14) | C14—C13—C12 | 119.5 (5) |
O13—Er1—N1 | 79.63 (14) | C14—C13—H13 | 120.2 |
N2—Er1—N1 | 65.87 (14) | C12—C13—H13 | 120.2 |
O12—Er1—N1 | 125.06 (13) | C15—C14—C13 | 118.3 (5) |
N3—Er1—N1 | 130.80 (14) | C15—C14—H14 | 120.9 |
O5—Er2—O7i | 75.68 (15) | C13—C14—H14 | 120.9 |
O5—Er2—O9iii | 99.68 (14) | N3—C15—C14 | 124.0 (5) |
O7i—Er2—O9iii | 82.37 (13) | N3—C15—H15 | 118.0 |
O5—Er2—O12 | 90.98 (13) | C14—C15—H15 | 118.0 |
O7i—Er2—O12 | 86.30 (13) | C17—C16—C21 | 118.5 (5) |
O9iii—Er2—O12 | 161.98 (13) | C17—C16—C8 | 115.4 (5) |
O5—Er2—O11i | 152.70 (14) | C21—C16—C8 | 126.0 (5) |
O7i—Er2—O11i | 131.61 (14) | C16—C17—C18 | 121.2 (6) |
O9iii—Er2—O11i | 86.03 (14) | C16—C17—H17 | 119.4 |
O12—Er2—O11i | 91.13 (14) | C18—C17—H17 | 119.4 |
O5—Er2—O10i | 151.32 (14) | C19—C18—C17 | 120.6 (6) |
O7i—Er2—O10i | 76.42 (14) | C19—C18—H18 | 119.7 |
O9iii—Er2—O10i | 83.01 (14) | C17—C18—H18 | 119.7 |
O12—Er2—O10i | 80.73 (13) | C20—C19—C18 | 118.5 (6) |
O11i—Er2—O10i | 55.56 (13) | C20—C19—H19 | 120.7 |
O5—Er2—O8 | 75.21 (14) | C18—C19—H19 | 120.7 |
O7i—Er2—O8 | 144.81 (13) | C19—C20—C21 | 122.5 (5) |
O9iii—Er2—O8 | 121.77 (13) | C19—C20—H20 | 118.8 |
O12—Er2—O8 | 74.90 (13) | C21—C20—H20 | 118.8 |
O11i—Er2—O8 | 79.11 (14) | C20—C21—C16 | 118.6 (5) |
O10i—Er2—O8 | 127.61 (14) | C20—C21—S1 | 117.4 (4) |
O5—Er2—O9 | 80.20 (13) | C16—C21—S1 | 123.9 (4) |
O7i—Er2—O9 | 137.73 (13) | O5—C22—O4 | 123.6 (5) |
O9iii—Er2—O9 | 68.03 (15) | O5—C22—C23 | 119.1 (5) |
O12—Er2—O9 | 128.61 (12) | O4—C22—C23 | 117.3 (5) |
O11i—Er2—O9 | 77.28 (13) | C22—C23—C24 | 108.3 (4) |
O10i—Er2—O9 | 126.14 (13) | C22—C23—H23A | 110.0 |
O8—Er2—O9 | 53.83 (12) | C24—C23—H23A | 110.0 |
O5—Er2—C31i | 177.65 (15) | C22—C23—H23B | 110.0 |
O7i—Er2—C31i | 103.59 (16) | C24—C23—H23B | 110.0 |
O9iii—Er2—C31i | 82.38 (15) | H23A—C23—H23B | 108.4 |
O12—Er2—C31i | 86.74 (15) | C23—C24—C25 | 112.1 (5) |
O11i—Er2—C31i | 28.11 (15) | C23—C24—H24A | 109.2 |
O10i—Er2—C31i | 27.52 (14) | C25—C24—H24A | 109.2 |
O8—Er2—C31i | 104.70 (16) | C23—C24—H24B | 109.2 |
O9—Er2—C31i | 101.67 (15) | C25—C24—H24B | 109.2 |
O5—Er2—Er2iii | 89.58 (10) | H24A—C24—H24B | 107.9 |
O7i—Er2—Er2iii | 112.47 (10) | C26—C25—C24 | 108.7 (4) |
O9iii—Er2—Er2iii | 35.19 (9) | C26—C25—H25A | 110.0 |
O12—Er2—Er2iii | 160.71 (9) | C24—C25—H25A | 110.0 |
O11i—Er2—Er2iii | 79.78 (10) | C26—C25—H25B | 110.0 |
O10i—Er2—Er2iii | 107.18 (10) | C24—C25—H25B | 110.0 |
O8—Er2—Er2iii | 86.63 (9) | H25A—C25—H25B | 108.3 |
O9—Er2—Er2iii | 32.84 (8) | O6—C26—O7 | 124.1 (5) |
C31i—Er2—Er2iii | 92.76 (12) | O6—C26—C25 | 117.9 (5) |
O2—S1—O3 | 115.2 (3) | O7—C26—C25 | 117.9 (5) |
O2—S1—O1 | 111.4 (3) | O8—C27—O9 | 118.4 (5) |
O3—S1—O1 | 112.1 (3) | O8—C27—C28 | 120.9 (5) |
O2—S1—C21 | 106.0 (3) | O9—C27—C28 | 120.7 (5) |
O3—S1—C21 | 108.0 (3) | C27—C28—C29 | 114.4 (5) |
O1—S1—C21 | 103.2 (2) | C27—C28—H28A | 108.7 |
C5—N1—C1 | 118.4 (5) | C29—C28—H28A | 108.7 |
C5—N1—Er1 | 120.4 (3) | C27—C28—H28B | 108.7 |
C1—N1—Er1 | 121.2 (3) | C29—C28—H28B | 108.7 |
C6—N2—C10 | 118.3 (5) | H28A—C28—H28B | 107.6 |
C6—N2—Er1 | 120.4 (3) | C28—C29—C30 | 112.7 (5) |
C10—N2—Er1 | 121.1 (3) | C28—C29—H29A | 109.1 |
C15—N3—C11 | 117.6 (5) | C30—C29—H29A | 109.1 |
C15—N3—Er1 | 121.6 (4) | C28—C29—H29B | 109.1 |
C11—N3—Er1 | 120.6 (3) | C30—C29—H29B | 109.1 |
S1—O1—Er1ii | 152.9 (3) | H29A—C29—H29B | 107.8 |
C22—O4—Er1 | 154.3 (4) | C31—C30—C29 | 114.1 (5) |
C22—O5—Er2 | 134.7 (4) | C31—C30—H30A | 108.7 |
C26—O6—Er1iv | 145.1 (4) | C29—C30—H30A | 108.7 |
C26—O7—Er2iv | 140.7 (4) | C31—C30—H30B | 108.7 |
C27—O8—Er2 | 94.6 (3) | C29—C30—H30B | 108.7 |
C27—O9—Er2iii | 154.7 (4) | H30A—C30—H30B | 107.6 |
C27—O9—Er2 | 93.2 (3) | O10—C31—O11 | 120.9 (5) |
Er2iii—O9—Er2 | 111.97 (15) | O10—C31—C30 | 120.7 (5) |
C31—O10—Er2iv | 91.9 (3) | O11—C31—C30 | 118.4 (5) |
C31—O11—Er2iv | 91.3 (3) | O10—C31—Er2iv | 60.6 (3) |
C32—O12—Er2 | 134.7 (4) | O11—C31—Er2iv | 60.6 (3) |
C32—O12—Er1 | 90.1 (3) | C30—C31—Er2iv | 176.7 (4) |
Er2—O12—Er1 | 124.42 (16) | O13—C32—O12 | 119.1 (6) |
C32—O13—Er1 | 96.6 (4) | O13—C32—C33 | 122.7 (6) |
N1—C1—C2 | 122.9 (6) | O12—C32—C33 | 118.0 (6) |
N1—C1—H1 | 118.6 | C32—C33—C34 | 113.8 (6) |
C2—C1—H1 | 118.6 | C32—C33—H33A | 108.8 |
C3—C2—C1 | 119.0 (6) | C34—C33—H33A | 108.8 |
C3—C2—H2 | 120.5 | C32—C33—H33B | 108.8 |
C1—C2—H2 | 120.5 | C34—C33—H33B | 108.8 |
C2—C3—C4 | 118.1 (5) | H33A—C33—H33B | 107.7 |
C2—C3—H3 | 120.9 | C33v—C34—C33 | 106.7 (12) |
C4—C3—H3 | 120.9 | C33v—C34—H34A | 110.4 |
C5—C4—C3 | 120.3 (5) | C33—C34—H34A | 110.4 |
C5—C4—H4 | 119.9 | C33v—C34—H34B | 110.4 |
C3—C4—H4 | 119.9 | C33—C34—H34B | 110.4 |
N1—C5—C4 | 121.2 (5) | H34A—C34—H34B | 108.6 |
| | | |
O2—S1—O1—Er1ii | 98.8 (6) | C16—C17—C18—C19 | 1.2 (10) |
O3—S1—O1—Er1ii | −32.0 (7) | C17—C18—C19—C20 | −0.9 (10) |
C21—S1—O1—Er1ii | −147.9 (5) | C18—C19—C20—C21 | −1.7 (9) |
C5—N1—C1—C2 | −2.7 (8) | C19—C20—C21—C16 | 3.8 (9) |
Er1—N1—C1—C2 | 178.7 (4) | C19—C20—C21—S1 | −178.8 (5) |
N1—C1—C2—C3 | 1.0 (9) | C17—C16—C21—C20 | −3.3 (8) |
C1—C2—C3—C4 | −0.2 (9) | C8—C16—C21—C20 | 175.2 (5) |
C2—C3—C4—C5 | 1.1 (8) | C17—C16—C21—S1 | 179.5 (4) |
C1—N1—C5—C4 | 3.6 (8) | C8—C16—C21—S1 | −2.0 (8) |
Er1—N1—C5—C4 | −177.8 (4) | O2—S1—C21—C20 | 86.9 (5) |
C1—N1—C5—C6 | −176.9 (5) | O3—S1—C21—C20 | −149.1 (4) |
Er1—N1—C5—C6 | 1.7 (6) | O1—S1—C21—C20 | −30.3 (5) |
C3—C4—C5—N1 | −2.9 (8) | O2—S1—C21—C16 | −95.9 (5) |
C3—C4—C5—C6 | 177.7 (5) | O3—S1—C21—C16 | 28.1 (5) |
C10—N2—C6—C7 | 0.4 (8) | O1—S1—C21—C16 | 146.9 (5) |
Er1—N2—C6—C7 | −173.9 (4) | Er2—O5—C22—O4 | 6.8 (9) |
C10—N2—C6—C5 | 179.3 (4) | Er2—O5—C22—C23 | −171.2 (4) |
Er1—N2—C6—C5 | 5.0 (6) | Er1—O4—C22—O5 | 9.5 (12) |
N1—C5—C6—N2 | −4.4 (7) | Er1—O4—C22—C23 | −172.4 (6) |
C4—C5—C6—N2 | 175.1 (5) | O5—C22—C23—C24 | 88.4 (6) |
N1—C5—C6—C7 | 174.5 (5) | O4—C22—C23—C24 | −89.8 (6) |
C4—C5—C6—C7 | −6.0 (8) | C22—C23—C24—C25 | 173.2 (5) |
N2—C6—C7—C8 | 2.7 (8) | C23—C24—C25—C26 | −174.7 (5) |
C5—C6—C7—C8 | −176.2 (5) | Er1iv—O6—C26—O7 | −0.7 (10) |
C6—C7—C8—C9 | −2.9 (8) | Er1iv—O6—C26—C25 | −177.2 (4) |
C6—C7—C8—C16 | −179.9 (5) | Er2iv—O7—C26—O6 | −22.1 (9) |
C7—C8—C9—C10 | 0.3 (8) | Er2iv—O7—C26—C25 | 154.4 (4) |
C16—C8—C9—C10 | 177.1 (5) | C24—C25—C26—O6 | 92.7 (6) |
C6—N2—C10—C9 | −3.1 (7) | C24—C25—C26—O7 | −84.0 (6) |
Er1—N2—C10—C9 | 171.1 (4) | Er2—O8—C27—O9 | 1.7 (5) |
C6—N2—C10—C11 | 176.2 (4) | Er2—O8—C27—C28 | −175.8 (5) |
Er1—N2—C10—C11 | −9.7 (6) | Er2iii—O9—C27—O8 | 172.9 (5) |
C8—C9—C10—N2 | 2.8 (8) | Er2—O9—C27—O8 | −1.7 (5) |
C8—C9—C10—C11 | −176.4 (5) | Er2iii—O9—C27—C28 | −9.6 (12) |
C15—N3—C11—C12 | 1.3 (8) | Er2—O9—C27—C28 | 175.8 (5) |
Er1—N3—C11—C12 | −174.5 (4) | O8—C27—C28—C29 | −23.9 (8) |
C15—N3—C11—C10 | −177.9 (5) | O9—C27—C28—C29 | 158.6 (5) |
Er1—N3—C11—C10 | 6.3 (6) | C27—C28—C29—C30 | 173.2 (5) |
N2—C10—C11—N3 | 2.1 (7) | C28—C29—C30—C31 | −71.1 (7) |
C9—C10—C11—N3 | −178.6 (5) | Er2iv—O10—C31—O11 | −5.4 (6) |
N2—C10—C11—C12 | −177.0 (5) | Er2iv—O10—C31—C30 | 176.5 (5) |
C9—C10—C11—C12 | 2.2 (8) | Er2iv—O11—C31—O10 | 5.4 (6) |
N3—C11—C12—C13 | 0.0 (8) | Er2iv—O11—C31—C30 | −176.4 (5) |
C10—C11—C12—C13 | 179.1 (5) | C29—C30—C31—O10 | −0.4 (8) |
C11—C12—C13—C14 | −0.7 (9) | C29—C30—C31—O11 | −178.6 (5) |
C12—C13—C14—C15 | 0.0 (9) | Er1—O13—C32—O12 | −8.2 (6) |
C11—N3—C15—C14 | −2.1 (8) | Er1—O13—C32—C33 | 166.2 (7) |
Er1—N3—C15—C14 | 173.7 (4) | Er2—O12—C32—O13 | −135.1 (5) |
C13—C14—C15—N3 | 1.4 (9) | Er1—O12—C32—O13 | 7.8 (6) |
C7—C8—C16—C17 | 55.2 (7) | Er2—O12—C32—C33 | 50.2 (9) |
C9—C8—C16—C17 | −121.6 (6) | Er1—O12—C32—C33 | −166.9 (6) |
C7—C8—C16—C21 | −123.3 (6) | O13—C32—C33—C34 | 14.5 (12) |
C9—C8—C16—C21 | 59.9 (8) | O12—C32—C33—C34 | −171.0 (7) |
C21—C16—C17—C18 | 0.9 (9) | C32—C33—C34—C33v | −110.5 (8) |
C8—C16—C17—C18 | −177.8 (5) | | |
Symmetry codes: (i) x, y−1, 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···A | D—H | H···A | D···A | D—H···A |
C33—H33B···O11i | 0.97 | 2.66 | 3.346 (9) | 128 |
C33—H33B···O8 | 0.97 | 2.43 | 3.091 (11) | 125 |
C28—H28B···O10 | 0.97 | 2.51 | 3.100 (7) | 119 |
C25—H25B···O14vi | 0.97 | 2.66 | 3.612 (8) | 168 |
C15—H15···O12 | 0.93 | 2.62 | 3.072 (7) | 111 |
C15—H15···O10i | 0.93 | 2.59 | 3.425 (7) | 149 |
C12—H12···O14i | 0.93 | 2.40 | 3.310 (7) | 166 |
C1—H1···O4 | 0.93 | 2.33 | 2.967 (7) | 125 |
C33—H33B···O8 | 0.97 | 2.43 | 3.091 (11) | 125 |
C28—H28B···O10 | 0.97 | 2.51 | 3.100 (7) | 119 |
C15—H15···O12 | 0.93 | 2.62 | 3.072 (7) | 111 |
C15—H15···O10i | 0.93 | 2.59 | 3.425 (7) | 149 |
C12—H12···O14i | 0.93 | 2.40 | 3.310 (7) | 166 |
C1—H1···O4 | 0.93 | 2.33 | 2.967 (7) | 125 |
C1—H1···O4 | 0.93 | 2.33 | 2.967 (7) | 125 |
C12—H12···O14i | 0.93 | 2.40 | 3.310 (7) | 166 |
C15—H15···O10i | 0.93 | 2.59 | 3.425 (7) | 149 |
C15—H15···O12 | 0.93 | 2.62 | 3.072 (7) | 111 |
C25—H25B···O14vi | 0.97 | 2.66 | 3.612 (8) | 168 |
C28—H28B···O10 | 0.97 | 2.51 | 3.100 (7) | 119 |
C33—H33B···O8 | 0.97 | 2.43 | 3.091 (11) | 125 |
C1—H1···O4 | 0.93 | 2.33 | 2.967 (7) | 125 |
C12—H12···O14i | 0.93 | 2.40 | 3.310 (7) | 166 |
C15—H15···O10i | 0.93 | 2.59 | 3.425 (7) | 149 |
C15—H15···O12 | 0.93 | 2.62 | 3.072 (7) | 111 |
C25—H25B···O14vi | 0.97 | 2.66 | 3.612 (8) | 168 |
C28—H28B···O10 | 0.97 | 2.51 | 3.100 (7) | 119 |
C33—H33B···O8 | 0.97 | 2.43 | 3.091 (11) | 125 |
C33—H33B···O11i | 0.97 | 2.66 | 3.346 (9) | 128 |
Symmetry codes: (i) x, y−1, z; (vi) x, −y+2, z−1/2. |
Crystal data top
C67H58N6O26S2Yb4·4(O) | F(000) = 4216 |
Mr = 2183.47 | Dx = 2.016 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 39.474 (8) Å | Cell parameters from 2917 reflections |
b = 8.6567 (17) Å | θ = 2.4–25.3° |
c = 25.670 (5) Å | µ = 5.30 mm−1 |
β = 124.895 (2)° | T = 296 K |
V = 7195 (2) Å3 | Block, yellow |
Z = 4 | 0.12 × 0.10 × 0.08 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 4703 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.053 |
Absorption correction: multi-scan sadabs | θmax = 25.1°, θmin = 1.6° |
Tmin = 0.789, Tmax = 0.856 | h = −43→46 |
17507 measured reflections | k = −9→10 |
6366 independent reflections | l = −30→22 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-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 reflections | Δρmax = 1.00 e Å−3 |
492 parameters | Δρmin = −0.92 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Yb1 | 0.13568 (2) | 0.54182 (3) | 0.28109 (2) | 0.02122 (9) | |
Yb2 | 0.03415 (2) | 0.55663 (3) | 0.08921 (2) | 0.02319 (9) | |
S1 | 0.25400 (6) | 0.8856 (2) | 0.61052 (8) | 0.0314 (5) | |
N1 | 0.17019 (17) | 0.3112 (6) | 0.3486 (2) | 0.0265 (14) | |
N2 | 0.15559 (16) | 0.5702 (6) | 0.3905 (2) | 0.0241 (13) | |
N3 | 0.11110 (17) | 0.7817 (6) | 0.3014 (2) | 0.0276 (15) | |
O1 | 0.29624 (14) | 0.9044 (5) | 0.6677 (2) | 0.0340 (13) | |
O2 | 0.25352 (17) | 0.8332 (7) | 0.5570 (2) | 0.0565 (17) | |
O3 | 0.22934 (18) | 1.0210 (6) | 0.5988 (3) | 0.0667 (19) | |
O4 | 0.13842 (16) | 0.7150 (5) | 0.2181 (2) | 0.0384 (14) | |
O5 | 0.08974 (14) | 0.7012 (5) | 0.1148 (2) | 0.0321 (12) | |
O6 | 0.12980 (15) | 1.3781 (5) | 0.2097 (2) | 0.0362 (13) | |
O7 | 0.08168 (15) | 1.3807 (6) | 0.1050 (2) | 0.0384 (14) | |
O8 | 0.01253 (15) | 0.3178 (5) | 0.1090 (2) | 0.0375 (14) | |
O9 | −0.01044 (14) | 0.3640 (5) | 0.01067 (19) | 0.0277 (12) | |
O10 | −0.03145 (14) | −0.3754 (5) | 0.0634 (2) | 0.0350 (13) | |
O11 | 0.01484 (15) | −0.1916 (5) | 0.0969 (2) | 0.0346 (13) | |
O12 | 0.08102 (15) | 0.4360 (6) | 0.2824 (2) | 0.0382 (13) | |
O13 | 0.06128 (14) | 0.5603 (5) | 0.19553 (19) | 0.0274 (11) | |
C1 | 0.1779 (2) | 0.1848 (8) | 0.3263 (3) | 0.036 (2) | |
H1 | 0.1706 | 0.1861 | 0.2848 | 0.043* | |
C2 | 0.1962 (2) | 0.0544 (9) | 0.3621 (3) | 0.039 (2) | |
H2 | 0.2004 | −0.0310 | 0.3444 | 0.047* | |
C3 | 0.2083 (2) | 0.0497 (8) | 0.4237 (4) | 0.0365 (19) | |
H3 | 0.2206 | −0.0381 | 0.4485 | 0.044* | |
C4 | 0.2017 (2) | 0.1797 (7) | 0.4480 (3) | 0.0278 (17) | |
H4 | 0.2096 | 0.1802 | 0.4898 | 0.033* | |
C5 | 0.1831 (2) | 0.3105 (8) | 0.4099 (3) | 0.0252 (17) | |
C6 | 0.1762 (2) | 0.4555 (8) | 0.4339 (3) | 0.0263 (16) | |
C7 | 0.1916 (2) | 0.4731 (8) | 0.4977 (3) | 0.0285 (17) | |
H7 | 0.2049 | 0.3912 | 0.5257 | 0.034* | |
C8 | 0.1868 (2) | 0.6147 (8) | 0.5197 (3) | 0.0233 (16) | |
C9 | 0.1651 (2) | 0.7311 (8) | 0.4752 (3) | 0.0279 (17) | |
H9 | 0.1611 | 0.8264 | 0.4877 | 0.034* | |
C10 | 0.1493 (2) | 0.7035 (7) | 0.4117 (3) | 0.0234 (16) | |
C11 | 0.1239 (2) | 0.8210 (7) | 0.3616 (3) | 0.0223 (16) | |
C12 | 0.1128 (2) | 0.9621 (8) | 0.3741 (3) | 0.0288 (17) | |
H12 | 0.1210 | 0.9850 | 0.4152 | 0.035* | |
C13 | 0.0901 (2) | 1.0669 (8) | 0.3264 (3) | 0.0351 (19) | |
H13 | 0.0842 | 1.1637 | 0.3352 | 0.042* | |
C14 | 0.0760 (2) | 1.0268 (8) | 0.2654 (3) | 0.0345 (19) | |
H14 | 0.0595 | 1.0941 | 0.2318 | 0.041* | |
C15 | 0.0869 (2) | 0.8839 (8) | 0.2550 (3) | 0.0347 (19) | |
H15 | 0.0770 | 0.8570 | 0.2135 | 0.042* | |
C16 | 0.2035 (2) | 0.6272 (8) | 0.5889 (3) | 0.0250 (16) | |
C17 | 0.1900 (2) | 0.5171 (8) | 0.6117 (3) | 0.036 (2) | |
H17 | 0.1709 | 0.4438 | 0.5839 | 0.043* | |
C18 | 0.2039 (2) | 0.5126 (8) | 0.6748 (3) | 0.038 (2) | |
H18 | 0.1935 | 0.4386 | 0.6885 | 0.045* | |
C19 | 0.2329 (2) | 0.6165 (9) | 0.7173 (3) | 0.041 (2) | |
H19 | 0.2426 | 0.6131 | 0.7599 | 0.049* | |
C20 | 0.2473 (2) | 0.7265 (9) | 0.6955 (3) | 0.0335 (19) | |
H20 | 0.2675 | 0.7956 | 0.7244 | 0.040* | |
C21 | 0.2328 (2) | 0.7375 (7) | 0.6317 (3) | 0.0224 (16) | |
C22 | 0.1214 (2) | 0.7610 (7) | 0.1621 (3) | 0.0272 (17) | |
C23 | 0.1395 (2) | 0.8997 (7) | 0.1508 (3) | 0.0274 (17) | |
H23A | 0.1362 | 0.8896 | 0.1105 | 0.033* | |
H23B | 0.1687 | 0.9086 | 0.1843 | 0.033* | |
C24 | 0.1162 (2) | 1.0433 (8) | 0.1500 (3) | 0.0354 (19) | |
H24A | 0.0875 | 1.0364 | 0.1142 | 0.042* | |
H24B | 0.1171 | 1.0454 | 0.1886 | 0.042* | |
C25 | 0.1347 (2) | 1.1930 (7) | 0.1450 (3) | 0.0301 (18) | |
H25A | 0.1642 | 1.1952 | 0.1776 | 0.036* | |
H25B | 0.1303 | 1.1991 | 0.1039 | 0.036* | |
C26 | 0.1139 (2) | 1.3296 (7) | 0.1537 (3) | 0.0254 (17) | |
C27 | −0.0078 (2) | 0.2731 (8) | 0.0527 (3) | 0.0295 (18) | |
C28 | −0.0288 (2) | 0.1202 (8) | 0.0331 (3) | 0.036 (2) | |
H28A | −0.0117 | 0.0482 | 0.0289 | 0.043* | |
H28B | −0.0547 | 0.1307 | −0.0084 | 0.043* | |
C29 | −0.0377 (2) | 0.0516 (8) | 0.0794 (3) | 0.0343 (18) | |
H29A | −0.0127 | 0.0548 | 0.1222 | 0.041* | |
H29B | −0.0583 | 0.1146 | 0.0787 | 0.041* | |
C30 | −0.0532 (2) | −0.1153 (8) | 0.0629 (4) | 0.041 (2) | |
H30A | −0.0639 | −0.1443 | 0.0874 | 0.050* | |
H30B | −0.0760 | −0.1195 | 0.0183 | 0.050* | |
C31 | −0.0213 (2) | −0.2329 (8) | 0.0748 (3) | 0.0265 (17) | |
C32 | 0.0525 (2) | 0.4923 (9) | 0.2314 (3) | 0.0321 (19) | |
C33 | 0.0089 (3) | 0.4970 (16) | 0.2105 (4) | 0.105 (5) | |
H33A | −0.0088 | 0.4656 | 0.1664 | 0.126* | |
H33B | 0.0018 | 0.6025 | 0.2133 | 0.126* | |
C34 | 0.0000 | 0.3923 (19) | 0.2500 | 0.144 (10) | |
H34A | 0.0236 | 0.3268 | 0.2779 | 0.173* | 0.5 |
H34B | −0.0236 | 0.3268 | 0.2221 | 0.173* | 0.5 |
O14 | 0.14392 (19) | 0.1126 (7) | 0.5145 (3) | 0.072 (2) | |
O15 | 0.9035 (2) | 0.3985 (9) | −0.0016 (4) | 0.114 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Yb1 | 0.02104 (17) | 0.02171 (16) | 0.01488 (16) | −0.00128 (13) | 0.00673 (13) | −0.00071 (12) |
Yb2 | 0.02392 (18) | 0.02331 (17) | 0.01495 (16) | 0.00012 (14) | 0.00678 (13) | −0.00041 (13) |
S1 | 0.0240 (10) | 0.0338 (11) | 0.0241 (10) | −0.0050 (8) | 0.0065 (8) | 0.0038 (8) |
N1 | 0.026 (3) | 0.026 (3) | 0.025 (3) | 0.003 (3) | 0.013 (3) | 0.000 (3) |
N2 | 0.021 (3) | 0.020 (3) | 0.024 (3) | 0.001 (2) | 0.009 (3) | 0.004 (2) |
N3 | 0.031 (4) | 0.023 (3) | 0.015 (3) | −0.002 (3) | 0.005 (3) | 0.000 (2) |
O1 | 0.021 (3) | 0.044 (3) | 0.025 (3) | −0.011 (2) | 0.007 (2) | −0.002 (2) |
O2 | 0.059 (4) | 0.084 (4) | 0.030 (3) | −0.044 (3) | 0.027 (3) | −0.022 (3) |
O3 | 0.043 (4) | 0.039 (4) | 0.099 (5) | 0.007 (3) | 0.030 (4) | 0.027 (3) |
O4 | 0.046 (3) | 0.036 (3) | 0.025 (3) | −0.004 (3) | 0.016 (3) | 0.005 (2) |
O5 | 0.028 (3) | 0.035 (3) | 0.024 (3) | −0.001 (2) | 0.009 (2) | 0.004 (2) |
O6 | 0.048 (3) | 0.032 (3) | 0.021 (3) | 0.002 (2) | 0.015 (2) | −0.006 (2) |
O7 | 0.034 (3) | 0.037 (3) | 0.026 (3) | 0.008 (2) | 0.006 (2) | 0.002 (2) |
O8 | 0.045 (3) | 0.040 (3) | 0.015 (3) | −0.011 (3) | 0.010 (2) | −0.002 (2) |
O9 | 0.030 (3) | 0.029 (3) | 0.016 (2) | −0.003 (2) | 0.009 (2) | 0.004 (2) |
O10 | 0.029 (3) | 0.028 (3) | 0.038 (3) | −0.001 (2) | 0.013 (2) | −0.006 (2) |
O11 | 0.029 (3) | 0.029 (3) | 0.033 (3) | 0.003 (2) | 0.010 (2) | −0.001 (2) |
O12 | 0.032 (3) | 0.048 (3) | 0.022 (3) | −0.004 (3) | 0.008 (2) | 0.010 (2) |
O13 | 0.025 (3) | 0.037 (3) | 0.017 (2) | 0.004 (2) | 0.011 (2) | −0.005 (2) |
C1 | 0.039 (5) | 0.037 (5) | 0.022 (4) | 0.013 (4) | 0.011 (4) | 0.000 (3) |
C2 | 0.029 (4) | 0.041 (5) | 0.037 (5) | 0.010 (4) | 0.013 (4) | −0.008 (4) |
C3 | 0.027 (4) | 0.026 (4) | 0.045 (5) | 0.011 (4) | 0.014 (4) | 0.012 (4) |
C4 | 0.032 (4) | 0.027 (4) | 0.025 (4) | 0.002 (3) | 0.017 (3) | 0.010 (3) |
C5 | 0.017 (4) | 0.031 (4) | 0.016 (4) | −0.001 (3) | 0.003 (3) | 0.001 (3) |
C6 | 0.023 (4) | 0.032 (4) | 0.020 (4) | −0.012 (3) | 0.010 (3) | −0.005 (3) |
C7 | 0.029 (4) | 0.031 (4) | 0.018 (4) | −0.002 (3) | 0.010 (3) | 0.007 (3) |
C8 | 0.023 (4) | 0.030 (4) | 0.020 (4) | −0.007 (3) | 0.014 (3) | −0.005 (3) |
C9 | 0.031 (4) | 0.026 (4) | 0.024 (4) | −0.007 (3) | 0.013 (3) | −0.005 (3) |
C10 | 0.020 (4) | 0.023 (4) | 0.021 (4) | −0.008 (3) | 0.007 (3) | −0.004 (3) |
C11 | 0.020 (4) | 0.025 (4) | 0.015 (4) | −0.004 (3) | 0.006 (3) | −0.001 (3) |
C12 | 0.031 (4) | 0.033 (4) | 0.026 (4) | −0.001 (3) | 0.019 (3) | −0.004 (3) |
C13 | 0.042 (5) | 0.019 (4) | 0.036 (5) | 0.004 (3) | 0.017 (4) | 0.000 (3) |
C14 | 0.035 (5) | 0.033 (4) | 0.033 (4) | 0.014 (4) | 0.019 (4) | 0.007 (3) |
C15 | 0.038 (5) | 0.034 (4) | 0.022 (4) | 0.005 (4) | 0.011 (4) | 0.001 (3) |
C16 | 0.026 (4) | 0.030 (4) | 0.014 (4) | −0.001 (3) | 0.009 (3) | 0.001 (3) |
C17 | 0.038 (5) | 0.040 (5) | 0.022 (4) | −0.015 (4) | 0.013 (4) | −0.001 (3) |
C18 | 0.043 (5) | 0.041 (5) | 0.031 (4) | 0.003 (4) | 0.023 (4) | 0.016 (4) |
C19 | 0.042 (5) | 0.058 (6) | 0.021 (4) | 0.004 (4) | 0.018 (4) | 0.007 (4) |
C20 | 0.026 (4) | 0.049 (5) | 0.016 (4) | 0.002 (4) | 0.007 (3) | −0.004 (3) |
C21 | 0.020 (4) | 0.026 (4) | 0.011 (3) | 0.000 (3) | 0.003 (3) | 0.001 (3) |
C22 | 0.029 (4) | 0.019 (4) | 0.034 (5) | 0.009 (3) | 0.018 (4) | 0.001 (3) |
C23 | 0.025 (4) | 0.027 (4) | 0.026 (4) | 0.000 (3) | 0.012 (3) | 0.001 (3) |
C24 | 0.038 (5) | 0.031 (4) | 0.041 (5) | −0.005 (4) | 0.025 (4) | −0.003 (4) |
C25 | 0.034 (5) | 0.022 (4) | 0.037 (5) | 0.002 (3) | 0.022 (4) | −0.003 (3) |
C26 | 0.038 (5) | 0.014 (4) | 0.032 (4) | −0.004 (3) | 0.025 (4) | −0.004 (3) |
C27 | 0.028 (4) | 0.025 (4) | 0.034 (5) | 0.003 (3) | 0.017 (4) | 0.005 (3) |
C28 | 0.045 (5) | 0.035 (4) | 0.019 (4) | −0.005 (4) | 0.014 (4) | 0.009 (3) |
C29 | 0.037 (5) | 0.031 (4) | 0.045 (5) | 0.007 (4) | 0.029 (4) | 0.004 (4) |
C30 | 0.038 (5) | 0.031 (4) | 0.062 (6) | 0.000 (4) | 0.033 (4) | 0.008 (4) |
C31 | 0.031 (5) | 0.030 (4) | 0.018 (4) | 0.000 (3) | 0.013 (3) | 0.004 (3) |
C32 | 0.028 (4) | 0.050 (5) | 0.020 (4) | −0.005 (4) | 0.015 (4) | −0.011 (3) |
C33 | 0.051 (7) | 0.226 (15) | 0.040 (6) | −0.019 (8) | 0.027 (5) | 0.038 (7) |
C34 | 0.048 (11) | 0.074 (13) | 0.24 (2) | 0.000 | 0.039 (14) | 0.000 |
O14 | 0.060 (4) | 0.094 (5) | 0.053 (4) | −0.009 (4) | 0.027 (3) | −0.028 (3) |
O15 | 0.051 (5) | 0.095 (6) | 0.156 (7) | 0.004 (4) | 0.035 (5) | 0.015 (5) |
Geometric parameters (Å, º) top
Yb1—O6i | 2.222 (4) | C7—C8 | 1.407 (9) |
Yb1—O4 | 2.252 (5) | C7—H7 | 0.9300 |
Yb1—O1ii | 2.264 (4) | C8—C9 | 1.391 (9) |
Yb1—O12 | 2.362 (5) | C8—C16 | 1.504 (8) |
Yb1—N2 | 2.459 (5) | C9—C10 | 1.393 (8) |
Yb1—O13 | 2.469 (4) | C9—H9 | 0.9300 |
Yb1—N3 | 2.471 (6) | C10—C11 | 1.491 (8) |
Yb1—N1 | 2.478 (5) | C11—C12 | 1.395 (9) |
Yb2—O7i | 2.265 (5) | C12—C13 | 1.368 (9) |
Yb2—O5 | 2.272 (5) | C12—H12 | 0.9300 |
Yb2—O9iii | 2.275 (4) | C13—C14 | 1.374 (9) |
Yb2—O13 | 2.292 (4) | C13—H13 | 0.9300 |
Yb2—O10iv | 2.352 (5) | C14—C15 | 1.385 (9) |
Yb2—O11iv | 2.355 (5) | C14—H14 | 0.9300 |
Yb2—O8 | 2.399 (5) | C15—H15 | 0.9300 |
Yb2—O9 | 2.426 (4) | C16—C17 | 1.377 (9) |
Yb2—C31iv | 2.705 (7) | C16—C21 | 1.415 (8) |
Yb2—Yb2iii | 3.8830 (9) | C17—C18 | 1.380 (9) |
S1—O2 | 1.437 (5) | C17—H17 | 0.9300 |
S1—O3 | 1.441 (6) | C18—C19 | 1.372 (10) |
S1—O1 | 1.471 (4) | C18—H18 | 0.9300 |
S1—C21 | 1.778 (7) | C19—C20 | 1.382 (10) |
N1—C5 | 1.349 (7) | C19—H19 | 0.9300 |
N1—C1 | 1.349 (8) | C20—C21 | 1.395 (8) |
N2—C10 | 1.357 (8) | C20—H20 | 0.9300 |
N2—C6 | 1.360 (8) | C22—C23 | 1.508 (9) |
N3—C15 | 1.346 (8) | C23—C24 | 1.539 (9) |
N3—C11 | 1.364 (7) | C23—H23A | 0.9700 |
O1—Yb1ii | 2.264 (4) | C23—H23B | 0.9700 |
O4—C22 | 1.253 (7) | C24—C25 | 1.529 (9) |
O5—C22 | 1.252 (8) | C24—H24A | 0.9700 |
O6—C26 | 1.266 (7) | C24—H24B | 0.9700 |
O6—Yb1iv | 2.222 (4) | C25—C26 | 1.528 (9) |
O7—C26 | 1.247 (8) | C25—H25A | 0.9700 |
O7—Yb2iv | 2.265 (5) | C25—H25B | 0.9700 |
O8—C27 | 1.249 (7) | C27—C28 | 1.488 (9) |
O9—C27 | 1.289 (8) | C28—C29 | 1.540 (9) |
O9—Yb2iii | 2.275 (4) | C28—H28A | 0.9700 |
O10—C31 | 1.278 (8) | C28—H28B | 0.9700 |
O10—Yb2i | 2.352 (5) | C29—C30 | 1.531 (9) |
O11—C31 | 1.248 (8) | C29—H29A | 0.9700 |
O11—Yb2i | 2.355 (5) | C29—H29B | 0.9700 |
O12—C32 | 1.238 (8) | C30—C31 | 1.509 (10) |
O13—C32 | 1.296 (8) | C30—H30A | 0.9700 |
C1—C2 | 1.372 (9) | C30—H30B | 0.9700 |
C1—H1 | 0.9300 | C31—Yb2i | 2.705 (7) |
C2—C3 | 1.367 (9) | C32—C33 | 1.483 (12) |
C2—H2 | 0.9300 | C33—C34 | 1.541 (13) |
C3—C4 | 1.382 (9) | C33—H33A | 0.9700 |
C3—H3 | 0.9300 | C33—H33B | 0.9700 |
C4—C5 | 1.398 (8) | C34—C33v | 1.541 (13) |
C4—H4 | 0.9300 | C34—H34A | 0.9700 |
C5—C6 | 1.491 (9) | C34—H34B | 0.9700 |
C6—C7 | 1.390 (8) | | |
| | | |
O6i—Yb1—O4 | 81.82 (18) | N1—C5—C6 | 116.3 (6) |
O6i—Yb1—O1ii | 97.99 (18) | C4—C5—C6 | 122.7 (6) |
O4—Yb1—O1ii | 75.58 (17) | N2—C6—C7 | 122.5 (6) |
O6i—Yb1—O12 | 95.71 (18) | N2—C6—C5 | 116.1 (6) |
O4—Yb1—O12 | 133.46 (17) | C7—C6—C5 | 121.3 (6) |
O1ii—Yb1—O12 | 149.57 (15) | C6—C7—C8 | 120.0 (6) |
O6i—Yb1—N2 | 145.15 (17) | C6—C7—H7 | 120.0 |
O4—Yb1—N2 | 129.68 (17) | C8—C7—H7 | 120.0 |
O1ii—Yb1—N2 | 79.58 (17) | C9—C8—C7 | 117.5 (6) |
O12—Yb1—N2 | 73.72 (17) | C9—C8—C16 | 124.5 (6) |
O6i—Yb1—O13 | 78.34 (16) | C7—C8—C16 | 117.9 (6) |
O4—Yb1—O13 | 80.76 (17) | C8—C9—C10 | 119.3 (6) |
O1ii—Yb1—O13 | 156.34 (16) | C8—C9—H9 | 120.3 |
O12—Yb1—O13 | 53.59 (15) | C10—C9—H9 | 120.3 |
N2—Yb1—O13 | 116.74 (17) | N2—C10—C9 | 123.5 (6) |
O6i—Yb1—N3 | 147.37 (17) | N2—C10—C11 | 115.0 (6) |
O4—Yb1—N3 | 77.18 (18) | C9—C10—C11 | 121.5 (6) |
O1ii—Yb1—N3 | 100.59 (18) | N3—C11—C12 | 121.2 (6) |
O12—Yb1—N3 | 81.40 (18) | N3—C11—C10 | 115.9 (6) |
N2—Yb1—N3 | 65.31 (17) | C12—C11—C10 | 122.9 (6) |
O13—Yb1—N3 | 73.88 (16) | C13—C12—C11 | 120.4 (6) |
O6i—Yb1—N1 | 79.57 (17) | C13—C12—H12 | 119.8 |
O4—Yb1—N1 | 143.62 (19) | C11—C12—H12 | 119.8 |
O1ii—Yb1—N1 | 76.40 (17) | C12—C13—C14 | 118.9 (7) |
O12—Yb1—N1 | 79.56 (18) | C12—C13—H13 | 120.6 |
N2—Yb1—N1 | 65.98 (17) | C14—C13—H13 | 120.6 |
O13—Yb1—N1 | 124.93 (17) | C13—C14—C15 | 118.6 (6) |
N3—Yb1—N1 | 130.88 (18) | C13—C14—H14 | 120.7 |
O7i—Yb2—O5 | 75.79 (18) | C15—C14—H14 | 120.7 |
O7i—Yb2—O9iii | 99.77 (17) | N3—C15—C14 | 123.9 (7) |
O5—Yb2—O9iii | 82.30 (16) | N3—C15—H15 | 118.1 |
O7i—Yb2—O13 | 91.22 (16) | C14—C15—H15 | 118.1 |
O5—Yb2—O13 | 86.12 (16) | C17—C16—C21 | 118.7 (6) |
O9iii—Yb2—O13 | 161.53 (16) | C17—C16—C8 | 116.0 (6) |
O7i—Yb2—O10iv | 152.19 (17) | C21—C16—C8 | 125.2 (6) |
O5—Yb2—O10iv | 132.03 (17) | C16—C17—C18 | 121.9 (7) |
O9iii—Yb2—O10iv | 86.00 (17) | C16—C17—H17 | 119.1 |
O13—Yb2—O10iv | 91.18 (16) | C18—C17—H17 | 119.1 |
O7i—Yb2—O11iv | 151.88 (18) | C19—C18—C17 | 120.3 (7) |
O5—Yb2—O11iv | 76.79 (17) | C19—C18—H18 | 119.8 |
O9iii—Yb2—O11iv | 82.55 (16) | C17—C18—H18 | 119.8 |
O13—Yb2—O11iv | 80.82 (15) | C18—C19—C20 | 118.7 (7) |
O10iv—Yb2—O11iv | 55.57 (16) | C18—C19—H19 | 120.6 |
O7i—Yb2—O8 | 75.02 (19) | C20—C19—H19 | 120.6 |
O5—Yb2—O8 | 144.58 (16) | C19—C20—C21 | 122.3 (7) |
O9iii—Yb2—O8 | 122.17 (15) | C19—C20—H20 | 118.9 |
O13—Yb2—O8 | 74.92 (16) | C21—C20—H20 | 118.9 |
O10iv—Yb2—O8 | 78.88 (17) | C20—C21—C16 | 118.1 (6) |
O11iv—Yb2—O8 | 127.46 (19) | C20—C21—S1 | 117.3 (5) |
O7i—Yb2—O9 | 79.60 (16) | C16—C21—S1 | 124.6 (5) |
O5—Yb2—O9 | 137.76 (16) | O5—C22—O4 | 124.3 (7) |
O9iii—Yb2—O9 | 68.65 (18) | O5—C22—C23 | 117.5 (6) |
O13—Yb2—O9 | 128.45 (15) | O4—C22—C23 | 118.2 (6) |
O10iv—Yb2—O9 | 77.26 (16) | C22—C23—C24 | 107.5 (6) |
O11iv—Yb2—O9 | 126.18 (16) | C22—C23—H23A | 110.2 |
O8—Yb2—O9 | 53.63 (15) | C24—C23—H23A | 110.2 |
O7i—Yb2—C31iv | 177.99 (18) | C22—C23—H23B | 110.2 |
O5—Yb2—C31iv | 103.9 (2) | C24—C23—H23B | 110.2 |
O9iii—Yb2—C31iv | 82.14 (18) | H23A—C23—H23B | 108.5 |
O13—Yb2—C31iv | 86.77 (17) | C25—C24—C23 | 112.0 (6) |
O10iv—Yb2—C31iv | 28.19 (17) | C25—C24—H24A | 109.2 |
O11iv—Yb2—C31iv | 27.44 (17) | C23—C24—H24A | 109.2 |
O8—Yb2—C31iv | 104.6 (2) | C25—C24—H24B | 109.2 |
O9—Yb2—C31iv | 101.77 (18) | C23—C24—H24B | 109.2 |
O7i—Yb2—Yb2iii | 89.24 (11) | H24A—C24—H24B | 107.9 |
O5—Yb2—Yb2iii | 112.58 (11) | C26—C25—C24 | 108.7 (6) |
O9iii—Yb2—Yb2iii | 35.58 (11) | C26—C25—H25A | 110.0 |
O13—Yb2—Yb2iii | 160.77 (12) | C24—C25—H25A | 110.0 |
O10iv—Yb2—Yb2iii | 79.71 (11) | C26—C25—H25B | 110.0 |
O11iv—Yb2—Yb2iii | 107.03 (11) | C24—C25—H25B | 110.0 |
O8—Yb2—Yb2iii | 86.64 (11) | H25A—C25—H25B | 108.3 |
O9—Yb2—Yb2iii | 33.07 (10) | O7—C26—O6 | 125.4 (6) |
C31iv—Yb2—Yb2iii | 92.71 (14) | O7—C26—C25 | 117.0 (6) |
O2—S1—O3 | 114.7 (4) | O6—C26—C25 | 117.5 (6) |
O2—S1—O1 | 112.2 (3) | O8—C27—O9 | 118.1 (6) |
O3—S1—O1 | 111.3 (3) | O8—C27—C28 | 122.1 (6) |
O2—S1—C21 | 108.3 (3) | O9—C27—C28 | 119.8 (6) |
O3—S1—C21 | 105.7 (3) | C27—C28—C29 | 114.3 (6) |
O1—S1—C21 | 103.7 (3) | C27—C28—H28A | 108.7 |
C5—N1—C1 | 117.8 (6) | C29—C28—H28A | 108.7 |
C5—N1—Yb1 | 120.6 (4) | C27—C28—H28B | 108.7 |
C1—N1—Yb1 | 121.6 (4) | C29—C28—H28B | 108.7 |
C10—N2—C6 | 117.0 (6) | H28A—C28—H28B | 107.6 |
C10—N2—Yb1 | 122.0 (4) | C30—C29—C28 | 112.4 (6) |
C6—N2—Yb1 | 120.9 (4) | C30—C29—H29A | 109.1 |
C15—N3—C11 | 117.0 (6) | C28—C29—H29A | 109.1 |
C15—N3—Yb1 | 122.0 (5) | C30—C29—H29B | 109.1 |
C11—N3—Yb1 | 120.8 (4) | C28—C29—H29B | 109.1 |
S1—O1—Yb1ii | 153.3 (3) | H29A—C29—H29B | 107.9 |
C22—O4—Yb1 | 145.1 (5) | C31—C30—C29 | 115.2 (6) |
C22—O5—Yb2 | 140.4 (5) | C31—C30—H30A | 108.5 |
C26—O6—Yb1iv | 153.8 (4) | C29—C30—H30A | 108.5 |
C26—O7—Yb2iv | 133.0 (5) | C31—C30—H30B | 108.5 |
C27—O8—Yb2 | 95.3 (4) | C29—C30—H30B | 108.5 |
C27—O9—Yb2iii | 155.6 (4) | H30A—C30—H30B | 107.5 |
C27—O9—Yb2 | 92.9 (4) | O11—C31—O10 | 120.6 (7) |
Yb2iii—O9—Yb2 | 111.35 (18) | O11—C31—C30 | 120.2 (6) |
C31—O10—Yb2i | 91.5 (4) | O10—C31—C30 | 119.2 (7) |
C31—O11—Yb2i | 92.1 (4) | O11—C31—Yb2i | 60.4 (4) |
C32—O12—Yb1 | 96.7 (4) | O10—C31—Yb2i | 60.4 (4) |
C32—O13—Yb2 | 135.0 (4) | C30—C31—Yb2i | 176.8 (5) |
C32—O13—Yb1 | 90.2 (4) | O12—C32—O13 | 118.7 (7) |
Yb2—O13—Yb1 | 124.5 (2) | O12—C32—C33 | 123.9 (7) |
N1—C1—C2 | 122.9 (7) | O13—C32—C33 | 117.3 (7) |
N1—C1—H1 | 118.6 | C32—C33—C34 | 113.6 (8) |
C2—C1—H1 | 118.6 | C32—C33—H33A | 108.8 |
C3—C2—C1 | 120.2 (7) | C34—C33—H33A | 108.8 |
C3—C2—H2 | 119.9 | C32—C33—H33B | 108.8 |
C1—C2—H2 | 119.9 | C34—C33—H33B | 108.8 |
C2—C3—C4 | 117.8 (6) | H33A—C33—H33B | 107.7 |
C2—C3—H3 | 121.1 | C33—C34—C33v | 108.0 (15) |
C4—C3—H3 | 121.1 | C33—C34—H34A | 110.1 |
C3—C4—C5 | 120.2 (7) | C33v—C34—H34A | 110.1 |
C3—C4—H4 | 119.9 | C33—C34—H34B | 110.1 |
C5—C4—H4 | 119.9 | C33v—C34—H34B | 110.1 |
N1—C5—C4 | 121.1 (6) | H34A—C34—H34B | 108.4 |
| | | |
O2—S1—O1—Yb1ii | 31.2 (8) | C16—C17—C18—C19 | −1.9 (12) |
O3—S1—O1—Yb1ii | −98.9 (7) | C17—C18—C19—C20 | 0.9 (12) |
C21—S1—O1—Yb1ii | 147.8 (6) | C18—C19—C20—C21 | 1.5 (12) |
C5—N1—C1—C2 | 3.5 (11) | C19—C20—C21—C16 | −2.7 (11) |
Yb1—N1—C1—C2 | −178.6 (6) | C19—C20—C21—S1 | 179.6 (6) |
N1—C1—C2—C3 | −1.5 (12) | C17—C16—C21—C20 | 1.7 (10) |
C1—C2—C3—C4 | −0.3 (11) | C8—C16—C21—C20 | −175.5 (6) |
C2—C3—C4—C5 | 0.1 (11) | C17—C16—C21—S1 | 179.2 (6) |
C1—N1—C5—C4 | −3.6 (10) | C8—C16—C21—S1 | 2.0 (10) |
Yb1—N1—C5—C4 | 178.4 (5) | O2—S1—C21—C20 | 149.8 (5) |
C1—N1—C5—C6 | 176.5 (6) | O3—S1—C21—C20 | −86.8 (6) |
Yb1—N1—C5—C6 | −1.5 (8) | O1—S1—C21—C20 | 30.4 (6) |
C3—C4—C5—N1 | 1.9 (10) | O2—S1—C21—C16 | −27.7 (7) |
C3—C4—C5—C6 | −178.2 (7) | O3—S1—C21—C16 | 95.7 (6) |
C10—N2—C6—C7 | −1.9 (10) | O1—S1—C21—C16 | −147.1 (6) |
Yb1—N2—C6—C7 | 173.5 (5) | Yb2—O5—C22—O4 | 23.7 (11) |
C10—N2—C6—C5 | −179.5 (6) | Yb2—O5—C22—C23 | −155.0 (5) |
Yb1—N2—C6—C5 | −4.2 (8) | Yb1—O4—C22—O5 | −1.0 (13) |
N1—C5—C6—N2 | 3.6 (9) | Yb1—O4—C22—C23 | 177.6 (5) |
C4—C5—C6—N2 | −176.3 (6) | O5—C22—C23—C24 | 85.0 (7) |
N1—C5—C6—C7 | −174.1 (6) | O4—C22—C23—C24 | −93.7 (7) |
C4—C5—C6—C7 | 6.1 (10) | C22—C23—C24—C25 | 174.6 (6) |
N2—C6—C7—C8 | −1.5 (10) | C23—C24—C25—C26 | −172.4 (6) |
C5—C6—C7—C8 | 176.1 (6) | Yb2iv—O7—C26—O6 | −5.8 (11) |
C6—C7—C8—C9 | 2.5 (10) | Yb2iv—O7—C26—C25 | 171.6 (4) |
C6—C7—C8—C16 | 179.3 (6) | Yb1iv—O6—C26—O7 | −9.6 (16) |
C7—C8—C9—C10 | −0.3 (10) | Yb1iv—O6—C26—C25 | 172.9 (7) |
C16—C8—C9—C10 | −176.8 (6) | C24—C25—C26—O7 | −88.4 (8) |
C6—N2—C10—C9 | 4.3 (10) | C24—C25—C26—O6 | 89.2 (7) |
Yb1—N2—C10—C9 | −171.0 (5) | Yb2—O8—C27—O9 | −2.7 (7) |
C6—N2—C10—C11 | −175.6 (6) | Yb2—O8—C27—C28 | 177.5 (6) |
Yb1—N2—C10—C11 | 9.1 (8) | Yb2iii—O9—C27—O8 | −172.0 (8) |
C8—C9—C10—N2 | −3.3 (10) | Yb2—O9—C27—O8 | 2.7 (7) |
C8—C9—C10—C11 | 176.6 (6) | Yb2iii—O9—C27—C28 | 7.8 (16) |
C15—N3—C11—C12 | −1.0 (10) | Yb2—O9—C27—C28 | −177.5 (6) |
Yb1—N3—C11—C12 | 174.8 (5) | O8—C27—C28—C29 | 22.1 (10) |
C15—N3—C11—C10 | 177.8 (6) | O9—C27—C28—C29 | −157.7 (6) |
Yb1—N3—C11—C10 | −6.4 (8) | C27—C28—C29—C30 | −171.3 (6) |
N2—C10—C11—N3 | −1.6 (9) | C28—C29—C30—C31 | 70.5 (8) |
C9—C10—C11—N3 | 178.5 (6) | Yb2i—O11—C31—O10 | 5.2 (6) |
N2—C10—C11—C12 | 177.2 (6) | Yb2i—O11—C31—C30 | −176.4 (6) |
C9—C10—C11—C12 | −2.8 (10) | Yb2i—O10—C31—O11 | −5.3 (6) |
N3—C11—C12—C13 | −2.5 (11) | Yb2i—O10—C31—C30 | 176.4 (6) |
C10—C11—C12—C13 | 178.8 (6) | C29—C30—C31—O11 | 0.3 (10) |
C11—C12—C13—C14 | 4.3 (11) | C29—C30—C31—O10 | 178.6 (6) |
C12—C13—C14—C15 | −2.7 (11) | Yb1—O12—C32—O13 | 9.2 (7) |
C11—N3—C15—C14 | 2.7 (11) | Yb1—O12—C32—C33 | −166.3 (9) |
Yb1—N3—C15—C14 | −173.0 (6) | Yb2—O13—C32—O12 | 134.8 (5) |
C13—C14—C15—N3 | −0.9 (12) | Yb1—O13—C32—O12 | −8.7 (7) |
C9—C8—C16—C17 | 122.3 (8) | Yb2—O13—C32—C33 | −49.4 (11) |
C7—C8—C16—C17 | −54.3 (9) | Yb1—O13—C32—C33 | 167.0 (8) |
C9—C8—C16—C21 | −60.5 (10) | O12—C32—C33—C34 | −13.7 (15) |
C7—C8—C16—C21 | 123.0 (8) | O13—C32—C33—C34 | 170.9 (9) |
C21—C16—C17—C18 | 0.5 (11) | C32—C33—C34—C33v | 110.7 (10) |
C8—C16—C17—C18 | 178.0 (7) | | |
Symmetry codes: (i) x, y−1, 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. |
Crystal data top
2(C29H18N3O7STb)·O | F(000) = 1416 |
Mr = 1438.89 | Dx = 1.820 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.0175 (18) Å | Cell parameters from 2199 reflections |
b = 16.994 (3) Å | θ = 2.3–21.3° |
c = 14.608 (2) Å | µ = 2.83 mm−1 |
β = 106.227 (3)° | T = 296 K |
V = 2626.0 (7) Å3 | Block, yellow |
Z = 2 | 0.13 × 0.10 × 0.09 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 3364 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.061 |
Absorption correction: multi-scan sadabs | θmax = 25.1°, θmin = 1.9° |
Tmin = 0.634, Tmax = 0.768 | h = −11→13 |
13056 measured reflections | k = −20→15 |
4647 independent reflections | l = −15→17 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-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 reflections | Δρmax = 1.40 e Å−3 |
379 parameters | Δρmin = −0.88 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Tb1 | 0.44863 (3) | 0.02537 (2) | 0.31007 (2) | 0.02328 (11) | |
S1 | 1.13235 (19) | −0.04248 (11) | 0.28158 (15) | 0.0451 (5) | |
N1 | 0.4208 (5) | −0.0436 (3) | 0.1503 (4) | 0.0378 (15) | |
N2 | 0.6466 (5) | −0.0188 (3) | 0.2718 (4) | 0.0342 (13) | |
N3 | 0.6500 (5) | 0.0922 (3) | 0.4003 (4) | 0.0363 (14) | |
O1 | 1.2655 (4) | −0.0469 (3) | 0.2817 (3) | 0.0421 (12) | |
O2 | 1.1206 (6) | −0.0057 (3) | 0.3678 (5) | 0.077 (2) | |
O3 | 1.0500 (6) | −0.0112 (3) | 0.1949 (5) | 0.082 (2) | |
O4 | 0.4821 (5) | 0.1402 (3) | 0.2233 (3) | 0.0493 (14) | |
O5 | 0.2882 (5) | 0.1064 (3) | 0.2161 (3) | 0.0489 (14) | |
O6 | 0.3963 (5) | 0.4208 (3) | −0.0677 (3) | 0.0442 (13) | |
O7 | 0.4776 (5) | 0.4251 (3) | 0.0911 (3) | 0.0422 (12) | |
C1 | 0.3108 (7) | −0.0401 (5) | 0.0807 (5) | 0.047 (2) | |
H1 | 0.2415 | −0.0169 | 0.0946 | 0.057* | |
C2 | 0.2959 (8) | −0.0688 (5) | −0.0091 (5) | 0.052 (2) | |
H2 | 0.2184 | −0.0648 | −0.0552 | 0.063* | |
C3 | 0.3968 (8) | −0.1035 (5) | −0.0303 (5) | 0.058 (2) | |
H3 | 0.3895 | −0.1227 | −0.0913 | 0.069* | |
C4 | 0.5102 (8) | −0.1096 (4) | 0.0409 (5) | 0.049 (2) | |
H4 | 0.5796 | −0.1340 | 0.0287 | 0.059* | |
C5 | 0.5188 (7) | −0.0790 (4) | 0.1297 (5) | 0.0380 (17) | |
C6 | 0.6417 (7) | −0.0762 (4) | 0.2057 (5) | 0.0372 (17) | |
C7 | 0.7439 (7) | −0.1233 (4) | 0.2077 (5) | 0.0388 (18) | |
H7 | 0.7373 | −0.1618 | 0.1613 | 0.047* | |
C8 | 0.8571 (7) | −0.1137 (4) | 0.2785 (5) | 0.0340 (16) | |
C9 | 0.8621 (7) | −0.0546 (4) | 0.3442 (5) | 0.0371 (17) | |
H9 | 0.9357 | −0.0466 | 0.3932 | 0.045* | |
C10 | 0.7591 (7) | −0.0080 (4) | 0.3372 (5) | 0.0361 (17) | |
C11 | 0.7629 (7) | 0.0638 (4) | 0.3963 (4) | 0.0343 (17) | |
C12 | 0.8775 (7) | 0.1033 (5) | 0.4358 (5) | 0.047 (2) | |
H12 | 0.9537 | 0.0817 | 0.4325 | 0.056* | |
C13 | 0.8741 (8) | 0.1751 (5) | 0.4799 (5) | 0.053 (2) | |
H13 | 0.9486 | 0.2023 | 0.5075 | 0.064* | |
C14 | 0.7589 (9) | 0.2058 (5) | 0.4824 (5) | 0.056 (2) | |
H14 | 0.7542 | 0.2543 | 0.5105 | 0.068* | |
C15 | 0.6504 (7) | 0.1624 (4) | 0.4418 (5) | 0.047 (2) | |
H15 | 0.5732 | 0.1835 | 0.4437 | 0.056* | |
C16 | 0.9649 (7) | −0.1679 (4) | 0.2811 (5) | 0.0348 (17) | |
C17 | 0.9407 (7) | −0.2486 (4) | 0.2805 (5) | 0.0399 (18) | |
H17 | 0.8607 | −0.2654 | 0.2813 | 0.048* | |
C18 | 1.0313 (8) | −0.3045 (4) | 0.2787 (5) | 0.047 (2) | |
H18 | 1.0125 | −0.3578 | 0.2790 | 0.056* | |
C19 | 1.1503 (8) | −0.2799 (4) | 0.2765 (5) | 0.048 (2) | |
H19 | 1.2111 | −0.3170 | 0.2732 | 0.057* | |
C20 | 1.1791 (7) | −0.2009 (4) | 0.2793 (5) | 0.0415 (18) | |
H20 | 1.2598 | −0.1850 | 0.2791 | 0.050* | |
C21 | 1.0869 (7) | −0.1436 (4) | 0.2823 (5) | 0.0339 (16) | |
C22 | 0.3652 (8) | 0.1477 (4) | 0.1875 (5) | 0.0360 (17) | |
C23 | 0.3133 (7) | 0.2048 (4) | 0.1081 (5) | 0.0339 (17) | |
C24 | 0.1994 (7) | 0.1899 (4) | 0.0416 (5) | 0.0351 (17) | |
H24 | 0.1528 | 0.1459 | 0.0488 | 0.042* | |
C25 | 0.1529 (7) | 0.2393 (4) | −0.0360 (5) | 0.0408 (18) | |
H25 | 0.0773 | 0.2278 | −0.0815 | 0.049* | |
C26 | 0.2220 (7) | 0.3067 (4) | −0.0443 (5) | 0.0352 (17) | |
H26 | 0.1914 | 0.3408 | −0.0954 | 0.042* | |
C27 | 0.3365 (6) | 0.3233 (4) | 0.0235 (4) | 0.0290 (15) | |
C28 | 0.3825 (7) | 0.2724 (4) | 0.1004 (5) | 0.0332 (16) | |
H28 | 0.4583 | 0.2832 | 0.1461 | 0.040* | |
C29 | 0.4080 (7) | 0.3963 (4) | 0.0151 (5) | 0.0329 (16) | |
O8 | 0.9993 (16) | 0.9567 (10) | 0.0054 (14) | 0.144 (8) | 0.5 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Tb1 | 0.02827 (18) | 0.02210 (17) | 0.02125 (17) | 0.00072 (15) | 0.00988 (12) | −0.00018 (15) |
S1 | 0.0390 (12) | 0.0349 (11) | 0.0649 (14) | −0.0026 (8) | 0.0203 (10) | 0.0052 (9) |
N1 | 0.030 (4) | 0.051 (4) | 0.033 (3) | −0.002 (3) | 0.010 (3) | −0.006 (3) |
N2 | 0.032 (3) | 0.047 (4) | 0.025 (3) | −0.004 (3) | 0.011 (3) | 0.001 (3) |
N3 | 0.043 (4) | 0.036 (3) | 0.029 (3) | −0.004 (3) | 0.007 (3) | −0.007 (3) |
O1 | 0.033 (3) | 0.035 (3) | 0.061 (3) | −0.006 (2) | 0.018 (2) | −0.001 (2) |
O2 | 0.079 (5) | 0.062 (4) | 0.112 (5) | −0.025 (3) | 0.064 (4) | −0.047 (4) |
O3 | 0.061 (4) | 0.060 (4) | 0.109 (5) | 0.000 (3) | −0.002 (4) | 0.042 (4) |
O4 | 0.046 (4) | 0.046 (3) | 0.055 (3) | −0.003 (3) | 0.011 (3) | 0.021 (3) |
O5 | 0.045 (3) | 0.048 (3) | 0.058 (3) | 0.003 (3) | 0.021 (3) | 0.024 (3) |
O6 | 0.050 (3) | 0.052 (3) | 0.034 (3) | −0.004 (3) | 0.017 (2) | 0.009 (2) |
O7 | 0.057 (4) | 0.031 (3) | 0.041 (3) | −0.009 (2) | 0.018 (3) | −0.004 (2) |
C1 | 0.033 (5) | 0.071 (6) | 0.037 (4) | 0.004 (4) | 0.007 (4) | −0.013 (4) |
C2 | 0.047 (5) | 0.069 (6) | 0.039 (5) | −0.002 (4) | 0.008 (4) | −0.011 (4) |
C3 | 0.047 (6) | 0.084 (7) | 0.039 (5) | −0.008 (5) | 0.008 (4) | −0.028 (4) |
C4 | 0.051 (6) | 0.057 (5) | 0.046 (5) | 0.000 (4) | 0.026 (4) | −0.018 (4) |
C5 | 0.038 (5) | 0.043 (4) | 0.036 (4) | 0.001 (3) | 0.015 (4) | −0.007 (3) |
C6 | 0.037 (5) | 0.044 (4) | 0.034 (4) | −0.006 (3) | 0.016 (3) | −0.006 (4) |
C7 | 0.040 (5) | 0.038 (4) | 0.044 (4) | −0.002 (3) | 0.020 (4) | −0.009 (3) |
C8 | 0.033 (4) | 0.033 (4) | 0.042 (4) | −0.003 (3) | 0.018 (3) | 0.002 (3) |
C9 | 0.026 (4) | 0.048 (4) | 0.038 (4) | 0.000 (3) | 0.011 (3) | −0.004 (3) |
C10 | 0.035 (4) | 0.049 (5) | 0.026 (4) | −0.009 (3) | 0.010 (3) | −0.005 (3) |
C11 | 0.040 (5) | 0.035 (4) | 0.031 (4) | 0.001 (3) | 0.013 (3) | 0.004 (3) |
C12 | 0.035 (5) | 0.066 (6) | 0.036 (4) | −0.006 (4) | 0.005 (4) | −0.007 (4) |
C13 | 0.066 (7) | 0.059 (6) | 0.034 (4) | −0.022 (5) | 0.013 (4) | −0.013 (4) |
C14 | 0.072 (7) | 0.046 (5) | 0.051 (5) | −0.017 (5) | 0.018 (5) | −0.014 (4) |
C15 | 0.043 (5) | 0.047 (5) | 0.053 (5) | −0.003 (4) | 0.017 (4) | −0.006 (4) |
C16 | 0.035 (5) | 0.034 (4) | 0.039 (4) | 0.001 (3) | 0.018 (3) | 0.001 (3) |
C17 | 0.041 (5) | 0.043 (4) | 0.038 (4) | −0.007 (4) | 0.015 (4) | 0.000 (3) |
C18 | 0.062 (6) | 0.030 (4) | 0.045 (5) | −0.005 (4) | 0.011 (4) | 0.000 (4) |
C19 | 0.057 (6) | 0.039 (4) | 0.048 (5) | 0.012 (4) | 0.015 (4) | −0.001 (4) |
C20 | 0.035 (5) | 0.045 (5) | 0.046 (5) | 0.000 (3) | 0.015 (4) | 0.006 (4) |
C21 | 0.035 (4) | 0.031 (4) | 0.039 (4) | 0.000 (3) | 0.016 (3) | 0.000 (3) |
C22 | 0.050 (5) | 0.027 (4) | 0.035 (4) | −0.006 (3) | 0.018 (4) | 0.002 (3) |
C23 | 0.042 (5) | 0.030 (4) | 0.032 (4) | 0.001 (3) | 0.015 (3) | 0.007 (3) |
C24 | 0.038 (5) | 0.026 (4) | 0.041 (4) | −0.007 (3) | 0.011 (4) | 0.000 (3) |
C25 | 0.037 (5) | 0.046 (5) | 0.039 (4) | −0.008 (3) | 0.009 (4) | 0.000 (4) |
C26 | 0.038 (5) | 0.030 (4) | 0.040 (4) | 0.002 (3) | 0.015 (4) | 0.006 (3) |
C27 | 0.032 (4) | 0.025 (4) | 0.033 (4) | −0.002 (3) | 0.013 (3) | −0.002 (3) |
C28 | 0.037 (4) | 0.034 (4) | 0.030 (4) | 0.003 (3) | 0.013 (3) | 0.001 (3) |
C29 | 0.040 (5) | 0.026 (4) | 0.038 (4) | 0.005 (3) | 0.019 (4) | −0.001 (3) |
O8 | 0.090 (13) | 0.17 (2) | 0.147 (15) | −0.065 (14) | −0.008 (10) | 0.020 (16) |
Geometric parameters (Å, º) top
Tb1—O6i | 2.220 (4) | C4—C5 | 1.377 (9) |
Tb1—O7ii | 2.234 (5) | C5—C6 | 1.492 (10) |
Tb1—O1iii | 2.299 (4) | C6—C7 | 1.375 (9) |
Tb1—O5 | 2.355 (5) | C7—C8 | 1.389 (9) |
Tb1—O4 | 2.411 (5) | C8—C9 | 1.379 (9) |
Tb1—N3 | 2.512 (5) | C8—C16 | 1.494 (9) |
Tb1—N2 | 2.513 (5) | C9—C10 | 1.365 (9) |
Tb1—N1 | 2.553 (5) | C10—C11 | 1.488 (9) |
S1—O3 | 1.438 (6) | C11—C12 | 1.403 (9) |
S1—O2 | 1.444 (6) | C12—C13 | 1.385 (10) |
S1—O1 | 1.468 (5) | C13—C14 | 1.382 (11) |
S1—C21 | 1.791 (7) | C14—C15 | 1.388 (10) |
N1—C5 | 1.341 (8) | C16—C17 | 1.397 (9) |
N1—C1 | 1.348 (8) | C16—C21 | 1.402 (9) |
N2—C10 | 1.350 (8) | C17—C18 | 1.382 (10) |
N2—C6 | 1.363 (8) | C18—C19 | 1.385 (10) |
N3—C15 | 1.339 (8) | C19—C20 | 1.378 (10) |
N3—C11 | 1.351 (8) | C20—C21 | 1.416 (9) |
O1—Tb1iv | 2.299 (4) | C22—C23 | 1.498 (9) |
O4—C22 | 1.254 (8) | C23—C24 | 1.380 (9) |
O5—C22 | 1.258 (8) | C23—C28 | 1.399 (9) |
O6—C29 | 1.251 (7) | C24—C25 | 1.388 (9) |
O6—Tb1v | 2.220 (4) | C25—C26 | 1.399 (9) |
O7—C29 | 1.259 (7) | C26—C27 | 1.398 (9) |
O7—Tb1vi | 2.235 (5) | C27—C28 | 1.396 (8) |
C1—C2 | 1.367 (9) | C27—C29 | 1.494 (9) |
C2—C3 | 1.368 (10) | O8—O8vii | 1.48 (3) |
C3—C4 | 1.388 (10) | | |
| | | |
O6i—Tb1—O7ii | 85.63 (17) | C2—C3—C4 | 118.7 (7) |
O6i—Tb1—O1iii | 87.31 (17) | C5—C4—C3 | 119.3 (7) |
O7ii—Tb1—O1iii | 81.46 (17) | N1—C5—C4 | 122.2 (7) |
O6i—Tb1—O5 | 84.64 (17) | N1—C5—C6 | 116.1 (6) |
O7ii—Tb1—O5 | 154.22 (17) | C4—C5—C6 | 121.5 (6) |
O1iii—Tb1—O5 | 74.29 (17) | N2—C6—C7 | 122.1 (6) |
O6i—Tb1—O4 | 101.63 (18) | N2—C6—C5 | 113.4 (6) |
O7ii—Tb1—O4 | 151.10 (18) | C7—C6—C5 | 124.4 (6) |
O1iii—Tb1—O4 | 126.39 (17) | C6—C7—C8 | 120.5 (7) |
O5—Tb1—O4 | 54.60 (17) | C9—C8—C7 | 117.2 (6) |
O6i—Tb1—N3 | 77.39 (18) | C9—C8—C16 | 123.6 (6) |
O7ii—Tb1—N3 | 84.10 (18) | C7—C8—C16 | 119.2 (6) |
O1iii—Tb1—N3 | 159.69 (17) | C10—C9—C8 | 120.0 (7) |
O5—Tb1—N3 | 116.77 (18) | N2—C10—C9 | 123.6 (6) |
O4—Tb1—N3 | 70.59 (17) | N2—C10—C11 | 113.2 (6) |
O6i—Tb1—N2 | 137.59 (17) | C9—C10—C11 | 123.0 (6) |
O7ii—Tb1—N2 | 74.61 (17) | N3—C11—C12 | 123.0 (7) |
O1iii—Tb1—N2 | 124.96 (17) | N3—C11—C10 | 116.1 (6) |
O5—Tb1—N2 | 126.98 (17) | C12—C11—C10 | 120.5 (7) |
O4—Tb1—N2 | 81.65 (18) | C13—C12—C11 | 118.3 (7) |
N3—Tb1—N2 | 63.75 (18) | C14—C13—C12 | 119.3 (8) |
O6i—Tb1—N1 | 158.82 (18) | C13—C14—C15 | 118.5 (8) |
O7ii—Tb1—N1 | 99.77 (17) | N3—C15—C14 | 124.0 (8) |
O1iii—Tb1—N1 | 73.42 (17) | C17—C16—C21 | 117.9 (6) |
O5—Tb1—N1 | 81.76 (18) | C17—C16—C8 | 117.1 (6) |
O4—Tb1—N1 | 83.56 (17) | C21—C16—C8 | 124.9 (6) |
N3—Tb1—N1 | 123.36 (18) | C18—C17—C16 | 122.5 (7) |
N2—Tb1—N1 | 63.21 (18) | C17—C18—C19 | 119.1 (7) |
O3—S1—O2 | 114.8 (4) | C20—C19—C18 | 120.3 (7) |
O3—S1—O1 | 113.9 (3) | C19—C20—C21 | 120.6 (7) |
O2—S1—O1 | 110.7 (3) | C16—C21—C20 | 119.5 (6) |
O3—S1—C21 | 104.6 (3) | C16—C21—S1 | 123.4 (5) |
O2—S1—C21 | 108.5 (3) | C20—C21—S1 | 117.1 (5) |
O1—S1—C21 | 103.4 (3) | O4—C22—O5 | 120.9 (6) |
C5—N1—C1 | 117.5 (6) | O4—C22—C23 | 120.9 (6) |
C5—N1—Tb1 | 120.8 (4) | O5—C22—C23 | 118.2 (7) |
C1—N1—Tb1 | 121.4 (5) | C24—C23—C28 | 120.2 (6) |
C10—N2—C6 | 116.5 (6) | C24—C23—C22 | 120.1 (6) |
C10—N2—Tb1 | 118.9 (4) | C28—C23—C22 | 119.7 (6) |
C6—N2—Tb1 | 120.4 (4) | C23—C24—C25 | 121.3 (6) |
C15—N3—C11 | 116.8 (6) | C24—C25—C26 | 118.7 (7) |
C15—N3—Tb1 | 122.1 (5) | C27—C26—C25 | 120.6 (6) |
C11—N3—Tb1 | 120.3 (4) | C28—C27—C26 | 119.9 (6) |
S1—O1—Tb1iv | 143.0 (3) | C28—C27—C29 | 120.0 (6) |
C22—O4—Tb1 | 90.6 (4) | C26—C27—C29 | 120.1 (6) |
C22—O5—Tb1 | 93.1 (5) | C27—C28—C23 | 119.3 (6) |
C29—O6—Tb1v | 159.2 (5) | O6—C29—O7 | 126.6 (6) |
C29—O7—Tb1vi | 152.6 (4) | O6—C29—C27 | 116.2 (6) |
N1—C1—C2 | 123.3 (7) | O7—C29—C27 | 117.1 (6) |
C1—C2—C3 | 119.0 (7) | | |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) x−1, y, z; (iv) x+1, y, z; (v) x, −y+1/2, z−1/2; (vi) −x+1, y+1/2, −z+1/2; (vii) −x+2, −y+2, −z. |
Crystal data top
2(C29H18N3O7SYb)·O | F(000) = 1436 |
Mr = 1467.13 | Dx = 1.859 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.0067 (12) Å | Cell parameters from 3822 reflections |
b = 16.9842 (19) Å | θ = 2.4–26.2° |
c = 14.5971 (16) Å | µ = 3.71 mm−1 |
β = 106.203 (2)° | T = 296 K |
V = 2620.4 (5) Å3 | Block, yellow |
Z = 2 | 0.14 × 0.13 × 0.10 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 3881 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.040 |
Absorption correction: multi-scan sadabs | θmax = 25.1°, θmin = 2.3° |
Tmin = 0.567, Tmax = 0.678 | h = −13→11 |
12880 measured reflections | k = −14→20 |
4638 independent reflections | l = −17→17 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.030 | H-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 reflections | Δρmax = 0.62 e Å−3 |
379 parameters | Δρmin = −0.97 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Yb1 | 0.55123 (2) | 1.02537 (2) | 0.68995 (2) | 0.02117 (8) | |
S1 | −0.13273 (12) | 0.95704 (7) | 0.71853 (11) | 0.0338 (3) | |
N1 | 0.3491 (4) | 1.0927 (2) | 0.5989 (3) | 0.0267 (9) | |
N2 | 0.3532 (4) | 0.9805 (2) | 0.7280 (3) | 0.0228 (9) | |
N3 | 0.5793 (4) | 0.9567 (2) | 0.8498 (3) | 0.0273 (9) | |
O1 | −0.2654 (3) | 0.9526 (2) | 0.7188 (2) | 0.0313 (8) | |
O2 | −0.0519 (4) | 0.9883 (3) | 0.8044 (3) | 0.0648 (15) | |
O3 | −0.1206 (4) | 0.9936 (2) | 0.6326 (4) | 0.0623 (14) | |
O4 | 0.4776 (3) | 0.92488 (19) | 0.5905 (2) | 0.0301 (8) | |
O5 | 0.3970 (3) | 0.9206 (2) | 0.4327 (2) | 0.0313 (8) | |
O6 | 0.4814 (3) | 0.6398 (2) | 0.7230 (2) | 0.0386 (9) | |
O7 | 0.2882 (3) | 0.6064 (2) | 0.7157 (2) | 0.0363 (9) | |
C1 | 0.3488 (5) | 1.1626 (3) | 0.5576 (4) | 0.0367 (13) | |
H1 | 0.4260 | 1.1838 | 0.5559 | 0.044* | |
C2 | 0.2413 (5) | 1.2055 (3) | 0.5176 (4) | 0.0418 (14) | |
H2 | 0.2457 | 1.2539 | 0.4889 | 0.050* | |
C3 | 0.1271 (5) | 1.1748 (4) | 0.5209 (4) | 0.0415 (14) | |
H3 | 0.0523 | 1.2021 | 0.4941 | 0.050* | |
C4 | 0.1248 (5) | 1.1037 (3) | 0.5642 (3) | 0.0335 (12) | |
H4 | 0.0483 | 1.0823 | 0.5672 | 0.040* | |
C5 | 0.2365 (5) | 1.0637 (3) | 0.6035 (3) | 0.0267 (11) | |
C6 | 0.2427 (5) | 0.9928 (3) | 0.6629 (3) | 0.0258 (11) | |
C7 | 0.1369 (4) | 0.9451 (3) | 0.6553 (3) | 0.0270 (11) | |
H7 | 0.0634 | 0.9528 | 0.6059 | 0.032* | |
C8 | 0.1425 (4) | 0.8862 (3) | 0.7221 (3) | 0.0259 (11) | |
C9 | 0.2562 (4) | 0.8763 (3) | 0.7924 (3) | 0.0313 (12) | |
H9 | 0.2638 | 0.8375 | 0.8386 | 0.038* | |
C10 | 0.3587 (4) | 0.9246 (3) | 0.7937 (3) | 0.0254 (11) | |
C11 | 0.4805 (4) | 0.9217 (3) | 0.8700 (3) | 0.0263 (11) | |
C12 | 0.4903 (5) | 0.8896 (3) | 0.9594 (4) | 0.0399 (14) | |
H12 | 0.4215 | 0.8638 | 0.9709 | 0.048* | |
C13 | 0.6021 (5) | 0.8960 (4) | 1.0309 (4) | 0.0474 (16) | |
H13 | 0.6087 | 0.8769 | 1.0918 | 0.057* | |
C14 | 0.7036 (5) | 0.9312 (4) | 1.0102 (4) | 0.0440 (15) | |
H14 | 0.7807 | 0.9359 | 1.0566 | 0.053* | |
C15 | 0.6886 (5) | 0.9597 (3) | 0.9182 (4) | 0.0353 (13) | |
H15 | 0.7583 | 0.9820 | 0.9039 | 0.042* | |
C16 | 0.0347 (4) | 0.8316 (3) | 0.7187 (3) | 0.0253 (11) | |
C17 | 0.0590 (5) | 0.7513 (3) | 0.7197 (4) | 0.0329 (12) | |
H17 | 0.1392 | 0.7345 | 0.7191 | 0.039* | |
C18 | −0.0313 (5) | 0.6958 (3) | 0.7214 (4) | 0.0387 (13) | |
H18 | −0.0123 | 0.6425 | 0.7212 | 0.046* | |
C19 | −0.1495 (5) | 0.7196 (3) | 0.7234 (4) | 0.0359 (13) | |
H19 | −0.2105 | 0.6825 | 0.7261 | 0.043* | |
C20 | −0.1777 (4) | 0.7993 (3) | 0.7215 (4) | 0.0317 (12) | |
H20 | −0.2580 | 0.8152 | 0.7227 | 0.038* | |
C21 | −0.0878 (4) | 0.8557 (3) | 0.7176 (3) | 0.0240 (10) | |
C22 | 0.4088 (4) | 0.8961 (3) | 0.5156 (3) | 0.0212 (10) | |
C23 | 0.3348 (4) | 0.8227 (3) | 0.5240 (3) | 0.0200 (10) | |
C24 | 0.2222 (4) | 0.8056 (3) | 0.4556 (3) | 0.0269 (11) | |
H24 | 0.1925 | 0.8388 | 0.4034 | 0.032* | |
C25 | 0.1546 (4) | 0.7396 (3) | 0.4653 (3) | 0.0284 (11) | |
H25 | 0.0786 | 0.7286 | 0.4199 | 0.034* | |
C26 | 0.1989 (4) | 0.6896 (3) | 0.5418 (3) | 0.0270 (11) | |
H26 | 0.1517 | 0.6458 | 0.5490 | 0.032* | |
C27 | 0.3143 (4) | 0.7050 (3) | 0.6081 (3) | 0.0222 (10) | |
C28 | 0.3812 (4) | 0.7723 (3) | 0.6001 (3) | 0.0206 (10) | |
H28 | 0.4569 | 0.7836 | 0.6457 | 0.025* | |
C29 | 0.3639 (5) | 0.6480 (3) | 0.6878 (3) | 0.0252 (11) | |
O8 | 0.9993 (13) | 0.9560 (8) | 0.9956 (10) | 0.131 (6) | 0.5 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Yb1 | 0.02298 (13) | 0.02200 (12) | 0.01985 (12) | −0.00085 (9) | 0.00817 (9) | −0.00006 (9) |
S1 | 0.0248 (7) | 0.0264 (7) | 0.0530 (8) | 0.0026 (5) | 0.0152 (6) | −0.0048 (6) |
N1 | 0.031 (2) | 0.024 (2) | 0.025 (2) | 0.0006 (18) | 0.0086 (19) | 0.0045 (18) |
N2 | 0.022 (2) | 0.029 (2) | 0.0176 (19) | 0.0010 (18) | 0.0062 (17) | 0.0016 (18) |
N3 | 0.021 (2) | 0.034 (2) | 0.028 (2) | 0.0019 (17) | 0.0078 (18) | 0.0041 (19) |
O1 | 0.0234 (18) | 0.0305 (19) | 0.044 (2) | 0.0046 (14) | 0.0164 (16) | −0.0017 (17) |
O2 | 0.042 (3) | 0.045 (3) | 0.095 (4) | 0.003 (2) | −0.003 (3) | −0.039 (3) |
O3 | 0.064 (3) | 0.043 (2) | 0.101 (4) | 0.020 (2) | 0.059 (3) | 0.035 (3) |
O4 | 0.038 (2) | 0.0212 (18) | 0.0312 (18) | −0.0086 (16) | 0.0101 (16) | −0.0053 (16) |
O5 | 0.037 (2) | 0.0303 (19) | 0.0308 (18) | −0.0039 (16) | 0.0162 (16) | 0.0095 (16) |
O6 | 0.028 (2) | 0.042 (2) | 0.043 (2) | −0.0024 (17) | 0.0054 (17) | 0.0187 (18) |
O7 | 0.032 (2) | 0.035 (2) | 0.046 (2) | 0.0016 (17) | 0.0185 (18) | 0.0209 (18) |
C1 | 0.037 (3) | 0.040 (3) | 0.037 (3) | 0.000 (3) | 0.016 (3) | 0.007 (3) |
C2 | 0.053 (4) | 0.035 (3) | 0.036 (3) | 0.015 (3) | 0.011 (3) | 0.014 (3) |
C3 | 0.037 (3) | 0.053 (4) | 0.033 (3) | 0.020 (3) | 0.008 (3) | 0.008 (3) |
C4 | 0.026 (3) | 0.045 (3) | 0.028 (3) | 0.008 (2) | 0.005 (2) | 0.004 (3) |
C5 | 0.029 (3) | 0.033 (3) | 0.018 (2) | 0.004 (2) | 0.008 (2) | −0.001 (2) |
C6 | 0.028 (3) | 0.033 (3) | 0.021 (2) | 0.004 (2) | 0.014 (2) | 0.000 (2) |
C7 | 0.016 (2) | 0.039 (3) | 0.025 (2) | 0.002 (2) | 0.005 (2) | 0.002 (2) |
C8 | 0.020 (2) | 0.028 (3) | 0.035 (3) | 0.003 (2) | 0.018 (2) | −0.001 (2) |
C9 | 0.024 (3) | 0.040 (3) | 0.034 (3) | 0.001 (2) | 0.013 (2) | 0.009 (2) |
C10 | 0.022 (3) | 0.038 (3) | 0.020 (2) | 0.004 (2) | 0.013 (2) | 0.003 (2) |
C11 | 0.024 (3) | 0.031 (3) | 0.026 (2) | 0.005 (2) | 0.010 (2) | 0.009 (2) |
C12 | 0.031 (3) | 0.055 (4) | 0.039 (3) | 0.007 (3) | 0.018 (3) | 0.022 (3) |
C13 | 0.040 (3) | 0.075 (5) | 0.028 (3) | 0.014 (3) | 0.011 (3) | 0.024 (3) |
C14 | 0.034 (3) | 0.066 (4) | 0.026 (3) | 0.007 (3) | −0.002 (2) | 0.007 (3) |
C15 | 0.023 (3) | 0.050 (4) | 0.031 (3) | 0.001 (2) | 0.004 (2) | 0.010 (3) |
C16 | 0.024 (3) | 0.031 (3) | 0.021 (2) | 0.000 (2) | 0.007 (2) | −0.005 (2) |
C17 | 0.030 (3) | 0.039 (3) | 0.032 (3) | 0.006 (2) | 0.014 (2) | −0.002 (2) |
C18 | 0.046 (3) | 0.027 (3) | 0.037 (3) | 0.006 (3) | 0.002 (3) | −0.001 (2) |
C19 | 0.035 (3) | 0.031 (3) | 0.037 (3) | −0.008 (2) | 0.003 (2) | 0.002 (3) |
C20 | 0.018 (3) | 0.038 (3) | 0.040 (3) | −0.003 (2) | 0.010 (2) | 0.000 (3) |
C21 | 0.023 (3) | 0.024 (3) | 0.027 (2) | 0.002 (2) | 0.011 (2) | 0.000 (2) |
C22 | 0.022 (2) | 0.019 (2) | 0.025 (3) | 0.0001 (19) | 0.011 (2) | −0.002 (2) |
C23 | 0.022 (2) | 0.021 (2) | 0.019 (2) | −0.0023 (19) | 0.010 (2) | −0.003 (2) |
C24 | 0.031 (3) | 0.026 (3) | 0.023 (2) | 0.002 (2) | 0.007 (2) | 0.005 (2) |
C25 | 0.021 (3) | 0.032 (3) | 0.030 (3) | −0.005 (2) | 0.004 (2) | −0.003 (2) |
C26 | 0.030 (3) | 0.024 (3) | 0.029 (3) | −0.007 (2) | 0.010 (2) | −0.001 (2) |
C27 | 0.028 (3) | 0.021 (2) | 0.021 (2) | 0.004 (2) | 0.012 (2) | 0.004 (2) |
C28 | 0.021 (2) | 0.024 (3) | 0.017 (2) | −0.001 (2) | 0.0059 (19) | 0.000 (2) |
C29 | 0.032 (3) | 0.019 (2) | 0.023 (2) | −0.001 (2) | 0.006 (2) | 0.001 (2) |
O8 | 0.106 (10) | 0.145 (13) | 0.120 (11) | 0.045 (11) | −0.006 (9) | −0.034 (11) |
Geometric parameters (Å, º) top
Yb1—O5i | 2.222 (3) | C7—H7 | 0.9300 |
Yb1—O4 | 2.241 (3) | C8—C9 | 1.389 (6) |
Yb1—O1ii | 2.303 (3) | C8—C16 | 1.495 (6) |
Yb1—O7iii | 2.357 (3) | C9—C10 | 1.390 (6) |
Yb1—O6iii | 2.402 (3) | C9—H9 | 0.9300 |
Yb1—N2 | 2.513 (4) | C10—C11 | 1.486 (6) |
Yb1—N1 | 2.524 (4) | C11—C12 | 1.391 (6) |
Yb1—N3 | 2.549 (4) | C12—C13 | 1.378 (8) |
Yb1—C29iii | 2.732 (5) | C12—H12 | 0.9300 |
S1—O2 | 1.422 (4) | C13—C14 | 1.373 (8) |
S1—O3 | 1.439 (5) | C13—H13 | 0.9300 |
S1—O1 | 1.463 (3) | C14—C15 | 1.393 (7) |
S1—C21 | 1.792 (5) | C14—H14 | 0.9300 |
N1—C1 | 1.332 (6) | C15—H15 | 0.9300 |
N1—C5 | 1.352 (6) | C16—C17 | 1.389 (7) |
N2—C6 | 1.335 (6) | C16—C21 | 1.405 (6) |
N2—C10 | 1.339 (6) | C17—C18 | 1.375 (7) |
N3—C15 | 1.333 (6) | C17—H17 | 0.9300 |
N3—C11 | 1.342 (6) | C18—C19 | 1.370 (7) |
O1—Yb1iv | 2.303 (3) | C18—H18 | 0.9300 |
O4—C22 | 1.244 (5) | C19—C20 | 1.387 (7) |
O5—C22 | 1.252 (5) | C19—H19 | 0.9300 |
O5—Yb1i | 2.222 (3) | C20—C21 | 1.390 (6) |
O6—C29 | 1.258 (6) | C20—H20 | 0.9300 |
O6—Yb1v | 2.402 (3) | C22—C23 | 1.512 (6) |
O7—C29 | 1.245 (5) | C23—C28 | 1.382 (6) |
O7—Yb1v | 2.357 (3) | C23—C24 | 1.389 (6) |
C1—C2 | 1.372 (7) | C24—C25 | 1.374 (7) |
C1—H1 | 0.9300 | C24—H24 | 0.9300 |
C2—C3 | 1.374 (8) | C25—C26 | 1.380 (7) |
C2—H2 | 0.9300 | C25—H25 | 0.9300 |
C3—C4 | 1.367 (7) | C26—C27 | 1.390 (6) |
C3—H3 | 0.9300 | C26—H26 | 0.9300 |
C4—C5 | 1.381 (6) | C27—C28 | 1.382 (6) |
C4—H4 | 0.9300 | C27—C29 | 1.495 (6) |
C5—C6 | 1.473 (7) | C28—H28 | 0.9300 |
C6—C7 | 1.398 (7) | C29—Yb1v | 2.732 (5) |
C7—C8 | 1.387 (6) | O8—O8vi | 1.50 (3) |
| | | |
O5i—Yb1—O4 | 85.43 (12) | C7—C6—C5 | 121.8 (4) |
O5i—Yb1—O1ii | 87.70 (12) | C8—C7—C6 | 119.3 (4) |
O4—Yb1—O1ii | 81.36 (12) | C8—C7—H7 | 120.3 |
O5i—Yb1—O7iii | 84.86 (12) | C6—C7—H7 | 120.3 |
O4—Yb1—O7iii | 154.15 (12) | C7—C8—C9 | 117.4 (4) |
O1ii—Yb1—O7iii | 74.37 (12) | C7—C8—C16 | 123.0 (4) |
O5i—Yb1—O6iii | 101.63 (12) | C9—C8—C16 | 119.5 (4) |
O4—Yb1—O6iii | 151.43 (12) | C8—C9—C10 | 119.9 (5) |
O1ii—Yb1—O6iii | 126.15 (12) | C8—C9—H9 | 120.0 |
O7iii—Yb1—O6iii | 54.35 (11) | C10—C9—H9 | 120.0 |
O5i—Yb1—N2 | 137.41 (12) | N2—C10—C9 | 122.3 (4) |
O4—Yb1—N2 | 74.49 (12) | N2—C10—C11 | 114.3 (4) |
O1ii—Yb1—N2 | 124.52 (12) | C9—C10—C11 | 123.4 (4) |
O7iii—Yb1—N2 | 127.11 (12) | N3—C11—C12 | 121.6 (4) |
O6iii—Yb1—N2 | 82.07 (12) | N3—C11—C10 | 116.0 (4) |
O5i—Yb1—N1 | 77.04 (12) | C12—C11—C10 | 122.3 (4) |
O4—Yb1—N1 | 84.12 (13) | C13—C12—C11 | 119.9 (5) |
O1ii—Yb1—N1 | 159.70 (12) | C13—C12—H12 | 120.0 |
O7iii—Yb1—N1 | 116.76 (13) | C11—C12—H12 | 120.0 |
O6iii—Yb1—N1 | 70.87 (12) | C14—C13—C12 | 118.5 (5) |
N2—Yb1—N1 | 64.04 (12) | C14—C13—H13 | 120.8 |
O5i—Yb1—N3 | 158.93 (13) | C12—C13—H13 | 120.8 |
O4—Yb1—N3 | 100.02 (12) | C13—C14—C15 | 118.6 (5) |
O1ii—Yb1—N3 | 73.20 (12) | C13—C14—H14 | 120.7 |
O7iii—Yb1—N3 | 81.54 (13) | C15—C14—H14 | 120.7 |
O6iii—Yb1—N3 | 83.35 (13) | N3—C15—C14 | 123.2 (5) |
N2—Yb1—N3 | 63.27 (12) | N3—C15—H15 | 118.4 |
N1—Yb1—N3 | 123.57 (12) | C14—C15—H15 | 118.4 |
O5i—Yb1—C29iii | 95.38 (13) | C17—C16—C21 | 117.8 (4) |
O4—Yb1—C29iii | 178.74 (13) | C17—C16—C8 | 117.4 (4) |
O1ii—Yb1—C29iii | 99.63 (14) | C21—C16—C8 | 124.8 (4) |
O7iii—Yb1—C29iii | 27.05 (12) | C18—C17—C16 | 122.4 (5) |
O6iii—Yb1—C29iii | 27.43 (12) | C18—C17—H17 | 118.8 |
N2—Yb1—C29iii | 104.27 (13) | C16—C17—H17 | 118.8 |
N1—Yb1—C29iii | 95.12 (13) | C19—C18—C17 | 119.6 (5) |
N3—Yb1—C29iii | 79.56 (13) | C19—C18—H18 | 120.2 |
O2—S1—O3 | 114.9 (3) | C17—C18—H18 | 120.2 |
O2—S1—O1 | 113.4 (2) | C18—C19—C20 | 119.7 (5) |
O3—S1—O1 | 111.1 (2) | C18—C19—H19 | 120.2 |
O2—S1—C21 | 105.0 (2) | C20—C19—H19 | 120.2 |
O3—S1—C21 | 108.3 (2) | C19—C20—C21 | 121.1 (5) |
O1—S1—C21 | 103.2 (2) | C19—C20—H20 | 119.5 |
C1—N1—C5 | 117.4 (4) | C21—C20—H20 | 119.5 |
C1—N1—Yb1 | 122.2 (3) | C20—C21—C16 | 119.4 (4) |
C5—N1—Yb1 | 119.7 (3) | C20—C21—S1 | 117.4 (4) |
C6—N2—C10 | 118.1 (4) | C16—C21—S1 | 123.1 (4) |
C6—N2—Yb1 | 118.0 (3) | O4—C22—O5 | 126.3 (4) |
C10—N2—Yb1 | 120.3 (3) | O4—C22—C23 | 117.5 (4) |
C15—N3—C11 | 118.0 (4) | O5—C22—C23 | 116.1 (4) |
C15—N3—Yb1 | 121.4 (3) | C28—C23—C24 | 120.3 (4) |
C11—N3—Yb1 | 120.3 (3) | C28—C23—C22 | 119.3 (4) |
S1—O1—Yb1iv | 142.8 (2) | C24—C23—C22 | 120.4 (4) |
C22—O4—Yb1 | 153.0 (3) | C25—C24—C23 | 119.8 (4) |
C22—O5—Yb1i | 159.2 (3) | C25—C24—H24 | 120.1 |
C29—O6—Yb1v | 91.0 (3) | C23—C24—H24 | 120.1 |
C29—O7—Yb1v | 93.5 (3) | C24—C25—C26 | 120.4 (4) |
N1—C1—C2 | 124.0 (5) | C24—C25—H25 | 119.8 |
N1—C1—H1 | 118.0 | C26—C25—H25 | 119.8 |
C2—C1—H1 | 118.0 | C25—C26—C27 | 119.7 (4) |
C1—C2—C3 | 118.2 (5) | C25—C26—H26 | 120.1 |
C1—C2—H2 | 120.9 | C27—C26—H26 | 120.1 |
C3—C2—H2 | 120.9 | C28—C27—C26 | 120.1 (4) |
C4—C3—C2 | 119.0 (5) | C28—C27—C29 | 120.9 (4) |
C4—C3—H3 | 120.5 | C26—C27—C29 | 119.0 (4) |
C2—C3—H3 | 120.5 | C27—C28—C23 | 119.6 (4) |
C3—C4—C5 | 119.9 (5) | C27—C28—H28 | 120.2 |
C3—C4—H4 | 120.0 | C23—C28—H28 | 120.2 |
C5—C4—H4 | 120.0 | O7—C29—O6 | 120.6 (4) |
N1—C5—C4 | 121.5 (5) | O7—C29—C27 | 119.3 (4) |
N1—C5—C6 | 115.7 (4) | O6—C29—C27 | 120.0 (4) |
C4—C5—C6 | 122.4 (5) | O7—C29—Yb1v | 59.5 (2) |
N2—C6—C7 | 122.6 (4) | O6—C29—Yb1v | 61.5 (2) |
N2—C6—C5 | 115.5 (4) | C27—C29—Yb1v | 170.5 (3) |
| | | |
O2—S1—O1—Yb1iv | 84.4 (4) | C13—C14—C15—N3 | 2.1 (9) |
O3—S1—O1—Yb1iv | −46.7 (4) | C7—C8—C16—C17 | 125.9 (5) |
C21—S1—O1—Yb1iv | −162.6 (3) | C9—C8—C16—C17 | −51.3 (6) |
C5—N1—C1—C2 | −1.9 (8) | C7—C8—C16—C21 | −56.2 (7) |
Yb1—N1—C1—C2 | −171.8 (4) | C9—C8—C16—C21 | 126.6 (5) |
N1—C1—C2—C3 | 0.6 (8) | C21—C16—C17—C18 | −1.2 (7) |
C1—C2—C3—C4 | 0.4 (8) | C8—C16—C17—C18 | 176.8 (5) |
C2—C3—C4—C5 | −0.2 (8) | C16—C17—C18—C19 | −0.8 (8) |
C1—N1—C5—C4 | 2.1 (7) | C17—C18—C19—C20 | 1.5 (8) |
Yb1—N1—C5—C4 | 172.3 (3) | C18—C19—C20—C21 | −0.1 (8) |
C1—N1—C5—C6 | −170.5 (4) | C19—C20—C21—C16 | −2.0 (7) |
Yb1—N1—C5—C6 | −0.3 (5) | C19—C20—C21—S1 | −178.4 (4) |
C3—C4—C5—N1 | −1.1 (7) | C17—C16—C21—C20 | 2.6 (7) |
C3—C4—C5—C6 | 171.0 (5) | C8—C16—C21—C20 | −175.3 (4) |
C10—N2—C6—C7 | −6.3 (7) | C17—C16—C21—S1 | 178.8 (4) |
Yb1—N2—C6—C7 | 152.6 (4) | C8—C16—C21—S1 | 0.9 (7) |
C10—N2—C6—C5 | 169.6 (4) | O2—S1—C21—C20 | 116.3 (4) |
Yb1—N2—C6—C5 | −31.5 (5) | O3—S1—C21—C20 | −120.5 (4) |
N1—C5—C6—N2 | 20.8 (6) | O1—S1—C21—C20 | −2.7 (4) |
C4—C5—C6—N2 | −151.7 (5) | O2—S1—C21—C16 | −59.9 (5) |
N1—C5—C6—C7 | −163.2 (4) | O3—S1—C21—C16 | 63.2 (5) |
C4—C5—C6—C7 | 24.2 (7) | O1—S1—C21—C16 | −178.9 (4) |
N2—C6—C7—C8 | 5.2 (7) | Yb1—O4—C22—O5 | 50.3 (9) |
C5—C6—C7—C8 | −170.5 (4) | Yb1—O4—C22—C23 | −131.8 (5) |
C6—C7—C8—C9 | −1.8 (7) | Yb1i—O5—C22—O4 | 33.4 (12) |
C6—C7—C8—C16 | −179.1 (4) | Yb1i—O5—C22—C23 | −144.5 (7) |
C7—C8—C9—C10 | −0.1 (7) | O4—C22—C23—C28 | −27.4 (6) |
C16—C8—C9—C10 | 177.2 (4) | O5—C22—C23—C28 | 150.7 (4) |
C6—N2—C10—C9 | 4.2 (7) | O4—C22—C23—C24 | 153.3 (4) |
Yb1—N2—C10—C9 | −154.2 (4) | O5—C22—C23—C24 | −28.6 (6) |
C6—N2—C10—C11 | −172.8 (4) | C28—C23—C24—C25 | 2.1 (7) |
Yb1—N2—C10—C11 | 28.9 (5) | C22—C23—C24—C25 | −178.7 (4) |
C8—C9—C10—N2 | −1.0 (7) | C23—C24—C25—C26 | −0.9 (7) |
C8—C9—C10—C11 | 175.6 (4) | C24—C25—C26—C27 | −1.8 (7) |
C15—N3—C11—C12 | 0.1 (7) | C25—C26—C27—C28 | 3.4 (7) |
Yb1—N3—C11—C12 | −174.5 (4) | C25—C26—C27—C29 | −176.9 (4) |
C15—N3—C11—C10 | 176.0 (4) | C26—C27—C28—C23 | −2.3 (7) |
Yb1—N3—C11—C10 | 1.3 (6) | C29—C27—C28—C23 | 178.1 (4) |
N2—C10—C11—N3 | −19.2 (6) | C24—C23—C28—C27 | −0.5 (7) |
C9—C10—C11—N3 | 163.8 (5) | C22—C23—C28—C27 | −179.7 (4) |
N2—C10—C11—C12 | 156.6 (5) | Yb1v—O7—C29—O6 | −7.7 (5) |
C9—C10—C11—C12 | −20.3 (8) | Yb1v—O7—C29—C27 | 169.1 (4) |
N3—C11—C12—C13 | 2.6 (8) | Yb1v—O6—C29—O7 | 7.5 (5) |
C10—C11—C12—C13 | −173.0 (5) | Yb1v—O6—C29—C27 | −169.2 (4) |
C11—C12—C13—C14 | −3.0 (9) | C28—C27—C29—O7 | 152.9 (4) |
C12—C13—C14—C15 | 0.8 (9) | C26—C27—C29—O7 | −26.7 (6) |
C11—N3—C15—C14 | −2.5 (8) | C28—C27—C29—O6 | −30.3 (7) |
Yb1—N3—C15—C14 | 172.1 (4) | C26—C27—C29—O6 | 150.1 (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) x−1, y, z; (v) −x+1, y−1/2, −z+3/2; (vi) −x+2, −y+2, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···O8 | 0.93 | 2.65 | 3.289 (15) | 126 |
C7—H7···O3 | 0.93 | 2.27 | 2.880 (6) | 122 |
C1—H1···O5i | 0.93 | 2.60 | 3.103 (6) | 114 |
Symmetry code: (i) −x+1, −y+2, −z+1. |
Crystal data top
C29H18EuN3O7S | F(000) = 1392 |
Mr = 704.48 | Dx = 1.845 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.1596 (9) Å | Cell parameters from 5032 reflections |
b = 13.4942 (13) Å | θ = 2.3–26.3° |
c = 20.727 (2) Å | µ = 2.61 mm−1 |
β = 98.039 (2)° | T = 296 K |
V = 2536.7 (4) Å3 | Block, yellow |
Z = 4 | 0.24 × 0.18 × 0.12 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 3916 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.027 |
Absorption correction: multi-scan sadabs | θmax = 25.1°, θmin = 1.8° |
Tmin = 0.574, Tmax = 0.733 | h = −10→10 |
12565 measured reflections | k = −16→12 |
4478 independent reflections | l = −24→24 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.023 | H-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 reflections | Δρmax = 0.37 e Å−3 |
370 parameters | Δρmin = −0.35 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Eu1 | 0.27732 (2) | 0.08032 (2) | 0.05431 (2) | 0.02036 (6) | |
S1 | 0.28268 (10) | 0.50603 (7) | 0.27766 (4) | 0.0359 (2) | |
N1 | 0.5151 (3) | 0.10483 (18) | 0.13425 (12) | 0.0245 (6) | |
N2 | 0.3324 (3) | 0.25673 (18) | 0.09190 (11) | 0.0221 (5) | |
N3 | 0.1461 (3) | 0.21966 (18) | −0.01794 (12) | 0.0271 (6) | |
O1 | 0.2547 (3) | 0.56975 (17) | 0.33238 (11) | 0.0401 (6) | |
O2 | 0.1486 (3) | 0.4713 (2) | 0.23932 (12) | 0.0619 (8) | |
O3 | 0.3902 (3) | 0.43098 (18) | 0.29829 (13) | 0.0595 (8) | |
O4 | 0.3518 (2) | −0.08559 (14) | 0.06204 (10) | 0.0282 (5) | |
O5 | 0.5397 (2) | −0.12614 (16) | 0.01064 (10) | 0.0312 (5) | |
O6 | 0.1959 (2) | −0.00279 (15) | −0.04408 (9) | 0.0260 (5) | |
O7 | −0.0297 (2) | −0.06576 (16) | −0.06158 (11) | 0.0336 (5) | |
C1 | 0.6045 (4) | 0.0293 (2) | 0.15256 (16) | 0.0339 (8) | |
H1 | 0.5986 | −0.0269 | 0.1264 | 0.041* | |
C2 | 0.7056 (4) | 0.0302 (3) | 0.20843 (19) | 0.0526 (11) | |
H2 | 0.7692 | −0.0230 | 0.2189 | 0.063* | |
C3 | 0.7098 (5) | 0.1112 (3) | 0.2480 (2) | 0.0649 (14) | |
H3 | 0.7727 | 0.1124 | 0.2873 | 0.078* | |
C4 | 0.6203 (4) | 0.1911 (3) | 0.22942 (18) | 0.0511 (11) | |
H4 | 0.6244 | 0.2474 | 0.2555 | 0.061* | |
C5 | 0.5245 (3) | 0.1869 (2) | 0.17185 (15) | 0.0273 (7) | |
C6 | 0.4332 (3) | 0.2729 (2) | 0.14606 (14) | 0.0239 (7) | |
C7 | 0.4569 (3) | 0.3668 (2) | 0.17249 (15) | 0.0281 (7) | |
H7 | 0.5232 | 0.3757 | 0.2103 | 0.034* | |
C8 | 0.3819 (3) | 0.4478 (2) | 0.14261 (15) | 0.0262 (7) | |
C9 | 0.2878 (3) | 0.4311 (2) | 0.08546 (15) | 0.0268 (7) | |
H9 | 0.2399 | 0.4843 | 0.0631 | 0.032* | |
C10 | 0.2640 (3) | 0.3362 (2) | 0.06115 (13) | 0.0236 (7) | |
C11 | 0.1652 (3) | 0.3154 (2) | −0.00079 (14) | 0.0237 (7) | |
C12 | 0.0955 (4) | 0.3907 (2) | −0.03979 (17) | 0.0383 (9) | |
H12 | 0.1114 | 0.4566 | −0.0278 | 0.046* | |
C13 | 0.0030 (4) | 0.3674 (3) | −0.09620 (17) | 0.0426 (9) | |
H13 | −0.0426 | 0.4170 | −0.1229 | 0.051* | |
C14 | −0.0199 (4) | 0.2698 (3) | −0.11177 (16) | 0.0411 (9) | |
H14 | −0.0845 | 0.2518 | −0.1486 | 0.049* | |
C15 | 0.0533 (4) | 0.1983 (2) | −0.07258 (16) | 0.0369 (9) | |
H15 | 0.0382 | 0.1322 | −0.0843 | 0.044* | |
C16 | 0.4074 (3) | 0.5518 (2) | 0.16699 (14) | 0.0267 (7) | |
C17 | 0.4716 (4) | 0.6171 (2) | 0.12774 (16) | 0.0343 (8) | |
H17 | 0.5007 | 0.5943 | 0.0892 | 0.041* | |
C18 | 0.4933 (4) | 0.7157 (2) | 0.14471 (17) | 0.0416 (9) | |
H18 | 0.5401 | 0.7579 | 0.1186 | 0.050* | |
C19 | 0.4459 (4) | 0.7508 (3) | 0.19991 (17) | 0.0443 (10) | |
H19 | 0.4565 | 0.8176 | 0.2106 | 0.053* | |
C20 | 0.3818 (4) | 0.6868 (2) | 0.24002 (16) | 0.0383 (9) | |
H20 | 0.3498 | 0.7111 | 0.2776 | 0.046* | |
C21 | 0.3648 (4) | 0.5873 (2) | 0.22509 (15) | 0.0288 (7) | |
C22 | 0.4072 (3) | −0.1327 (2) | 0.01827 (14) | 0.0229 (7) | |
C23 | 0.3100 (3) | −0.2031 (2) | −0.02505 (14) | 0.0238 (7) | |
C24 | 0.3610 (4) | −0.2990 (2) | −0.03245 (16) | 0.0320 (8) | |
H24 | 0.4528 | −0.3173 | −0.0107 | 0.038* | |
C25 | 0.2782 (4) | −0.3677 (2) | −0.07141 (18) | 0.0399 (9) | |
H25 | 0.3139 | −0.4317 | −0.0753 | 0.048* | |
C26 | 0.1423 (4) | −0.3410 (3) | −0.10450 (18) | 0.0442 (9) | |
H26 | 0.0872 | −0.3864 | −0.1315 | 0.053* | |
C27 | 0.0891 (4) | −0.2468 (3) | −0.09722 (16) | 0.0376 (8) | |
H27 | −0.0030 | −0.2295 | −0.1191 | 0.045* | |
C28 | 0.1703 (3) | −0.1769 (2) | −0.05762 (14) | 0.0263 (7) | |
C29 | 0.1071 (3) | −0.0750 (2) | −0.05374 (14) | 0.0240 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Eu1 | 0.01913 (9) | 0.01965 (9) | 0.02190 (9) | −0.00021 (6) | 0.00141 (6) | −0.00154 (6) |
S1 | 0.0442 (5) | 0.0384 (5) | 0.0266 (4) | 0.0010 (4) | 0.0097 (4) | −0.0002 (4) |
N1 | 0.0243 (14) | 0.0227 (14) | 0.0264 (14) | 0.0013 (11) | 0.0031 (11) | 0.0018 (11) |
N2 | 0.0231 (13) | 0.0236 (14) | 0.0189 (13) | 0.0002 (11) | 0.0004 (11) | −0.0016 (11) |
N3 | 0.0297 (15) | 0.0229 (15) | 0.0263 (14) | 0.0002 (11) | −0.0045 (12) | −0.0033 (11) |
O1 | 0.0425 (15) | 0.0522 (16) | 0.0269 (12) | 0.0088 (12) | 0.0097 (11) | −0.0031 (11) |
O2 | 0.0624 (19) | 0.080 (2) | 0.0431 (16) | −0.0362 (16) | 0.0077 (14) | −0.0057 (15) |
O3 | 0.090 (2) | 0.0512 (17) | 0.0435 (16) | 0.0304 (15) | 0.0314 (15) | 0.0165 (13) |
O4 | 0.0305 (12) | 0.0253 (12) | 0.0284 (12) | 0.0037 (10) | 0.0029 (10) | −0.0018 (9) |
O5 | 0.0234 (13) | 0.0413 (14) | 0.0283 (12) | −0.0032 (10) | 0.0018 (10) | −0.0002 (10) |
O6 | 0.0241 (12) | 0.0263 (12) | 0.0273 (12) | −0.0002 (9) | 0.0021 (9) | −0.0018 (9) |
O7 | 0.0192 (12) | 0.0434 (15) | 0.0377 (13) | 0.0018 (10) | 0.0021 (10) | −0.0027 (10) |
C1 | 0.0311 (19) | 0.0305 (19) | 0.040 (2) | 0.0044 (15) | 0.0033 (16) | 0.0005 (16) |
C2 | 0.047 (2) | 0.037 (2) | 0.064 (3) | 0.0100 (18) | −0.026 (2) | 0.002 (2) |
C3 | 0.070 (3) | 0.048 (3) | 0.061 (3) | 0.010 (2) | −0.043 (2) | −0.002 (2) |
C4 | 0.064 (3) | 0.035 (2) | 0.045 (2) | 0.0021 (19) | −0.025 (2) | −0.0060 (17) |
C5 | 0.0250 (17) | 0.0283 (18) | 0.0277 (17) | −0.0020 (14) | 0.0009 (14) | 0.0012 (14) |
C6 | 0.0273 (17) | 0.0217 (17) | 0.0230 (16) | −0.0004 (13) | 0.0039 (13) | −0.0015 (13) |
C7 | 0.0301 (18) | 0.0317 (19) | 0.0220 (16) | −0.0011 (14) | 0.0013 (14) | −0.0061 (14) |
C8 | 0.0323 (18) | 0.0221 (17) | 0.0254 (17) | −0.0011 (13) | 0.0086 (14) | −0.0043 (13) |
C9 | 0.0331 (19) | 0.0223 (18) | 0.0234 (16) | 0.0029 (14) | −0.0015 (14) | 0.0006 (13) |
C10 | 0.0255 (17) | 0.0233 (17) | 0.0221 (16) | −0.0004 (13) | 0.0036 (13) | −0.0027 (13) |
C11 | 0.0238 (17) | 0.0233 (17) | 0.0229 (16) | −0.0007 (13) | −0.0007 (13) | −0.0022 (13) |
C12 | 0.047 (2) | 0.0245 (19) | 0.039 (2) | 0.0037 (16) | −0.0087 (17) | −0.0024 (15) |
C13 | 0.051 (2) | 0.036 (2) | 0.035 (2) | 0.0100 (18) | −0.0150 (18) | 0.0030 (16) |
C14 | 0.049 (2) | 0.037 (2) | 0.0307 (19) | 0.0029 (17) | −0.0159 (17) | −0.0022 (16) |
C15 | 0.043 (2) | 0.0287 (19) | 0.035 (2) | −0.0006 (16) | −0.0083 (17) | −0.0044 (15) |
C16 | 0.0327 (19) | 0.0224 (17) | 0.0219 (17) | 0.0012 (13) | −0.0063 (14) | −0.0009 (13) |
C17 | 0.049 (2) | 0.0312 (19) | 0.0226 (17) | −0.0018 (16) | 0.0032 (16) | 0.0019 (14) |
C18 | 0.053 (2) | 0.029 (2) | 0.041 (2) | −0.0054 (17) | −0.0013 (19) | 0.0103 (16) |
C19 | 0.059 (3) | 0.0234 (19) | 0.048 (2) | 0.0010 (18) | −0.004 (2) | −0.0012 (18) |
C20 | 0.049 (2) | 0.031 (2) | 0.034 (2) | 0.0071 (17) | 0.0000 (17) | −0.0121 (16) |
C21 | 0.0296 (18) | 0.0291 (18) | 0.0261 (17) | 0.0018 (14) | −0.0015 (14) | −0.0028 (14) |
C22 | 0.0273 (18) | 0.0183 (16) | 0.0222 (16) | 0.0011 (13) | −0.0001 (14) | 0.0057 (13) |
C23 | 0.0246 (17) | 0.0249 (17) | 0.0234 (16) | −0.0044 (13) | 0.0089 (13) | −0.0008 (13) |
C24 | 0.034 (2) | 0.0272 (19) | 0.0370 (19) | 0.0048 (14) | 0.0137 (16) | 0.0059 (15) |
C25 | 0.048 (2) | 0.0196 (18) | 0.056 (2) | −0.0022 (16) | 0.0225 (19) | −0.0075 (17) |
C26 | 0.049 (2) | 0.034 (2) | 0.051 (2) | −0.0154 (18) | 0.0135 (19) | −0.0177 (18) |
C27 | 0.0308 (19) | 0.038 (2) | 0.043 (2) | −0.0069 (16) | 0.0031 (16) | −0.0097 (17) |
C28 | 0.0249 (17) | 0.0264 (18) | 0.0288 (18) | −0.0069 (13) | 0.0076 (14) | −0.0039 (14) |
C29 | 0.0246 (17) | 0.0315 (18) | 0.0166 (15) | 0.0024 (14) | 0.0050 (13) | −0.0006 (13) |
Geometric parameters (Å, º) top
Eu1—O7i | 2.302 (2) | C7—H7 | 0.9300 |
Eu1—O4 | 2.339 (2) | C8—C9 | 1.382 (4) |
Eu1—O6 | 2.3553 (19) | C8—C16 | 1.499 (4) |
Eu1—O5ii | 2.374 (2) | C9—C10 | 1.383 (4) |
Eu1—O1iii | 2.411 (2) | C9—H9 | 0.9300 |
Eu1—N2 | 2.533 (2) | C10—C11 | 1.491 (4) |
Eu1—N1 | 2.567 (2) | C11—C12 | 1.396 (4) |
Eu1—N3 | 2.592 (2) | C12—C13 | 1.381 (4) |
S1—O3 | 1.435 (3) | C12—H12 | 0.9300 |
S1—O2 | 1.444 (3) | C13—C14 | 1.365 (5) |
S1—O1 | 1.474 (2) | C13—H13 | 0.9300 |
S1—C21 | 1.785 (3) | C14—C15 | 1.374 (4) |
N1—C1 | 1.329 (4) | C14—H14 | 0.9300 |
N1—C5 | 1.351 (4) | C15—H15 | 0.9300 |
N2—C10 | 1.355 (4) | C16—C17 | 1.385 (5) |
N2—C6 | 1.368 (3) | C16—C21 | 1.401 (4) |
N3—C11 | 1.345 (4) | C17—C18 | 1.383 (4) |
N3—C15 | 1.349 (4) | C17—H17 | 0.9300 |
O1—Eu1iv | 2.411 (2) | C18—C19 | 1.364 (5) |
O4—C22 | 1.270 (4) | C18—H18 | 0.9300 |
O5—C22 | 1.249 (4) | C19—C20 | 1.385 (5) |
O5—Eu1ii | 2.374 (2) | C19—H19 | 0.9300 |
O6—C29 | 1.267 (3) | C20—C21 | 1.382 (4) |
O7—C29 | 1.247 (4) | C20—H20 | 0.9300 |
O7—Eu1i | 2.302 (2) | C22—C23 | 1.510 (4) |
C1—C2 | 1.378 (4) | C23—C24 | 1.391 (4) |
C1—H1 | 0.9300 | C23—C28 | 1.406 (4) |
C2—C3 | 1.364 (5) | C24—C25 | 1.384 (4) |
C2—H2 | 0.9300 | C24—H24 | 0.9300 |
C3—C4 | 1.376 (5) | C25—C26 | 1.382 (5) |
C3—H3 | 0.9300 | C25—H25 | 0.9300 |
C4—C5 | 1.380 (4) | C26—C27 | 1.377 (5) |
C4—H4 | 0.9300 | C26—H26 | 0.9300 |
C5—C6 | 1.485 (4) | C27—C28 | 1.396 (4) |
C6—C7 | 1.385 (4) | C27—H27 | 0.9300 |
C7—C8 | 1.389 (4) | C28—C29 | 1.499 (4) |
| | | |
O7i—Eu1—O4 | 101.21 (8) | C8—C7—H7 | 119.9 |
O7i—Eu1—O6 | 79.65 (7) | C9—C8—C7 | 117.7 (3) |
O4—Eu1—O6 | 69.98 (7) | C9—C8—C16 | 119.3 (3) |
O7i—Eu1—O5ii | 147.09 (7) | C7—C8—C16 | 122.8 (3) |
O4—Eu1—O5ii | 93.77 (8) | C10—C9—C8 | 120.7 (3) |
O6—Eu1—O5ii | 78.24 (7) | C10—C9—H9 | 119.7 |
O7i—Eu1—O1iii | 71.09 (8) | C8—C9—H9 | 119.7 |
O4—Eu1—O1iii | 87.18 (8) | N2—C10—C9 | 121.5 (3) |
O6—Eu1—O1iii | 138.43 (7) | N2—C10—C11 | 116.2 (2) |
O5ii—Eu1—O1iii | 139.42 (7) | C9—C10—C11 | 122.2 (3) |
O7i—Eu1—N2 | 102.45 (8) | N3—C11—C12 | 120.9 (3) |
O4—Eu1—N2 | 146.57 (7) | N3—C11—C10 | 116.7 (3) |
O6—Eu1—N2 | 137.65 (7) | C12—C11—C10 | 122.4 (3) |
O5ii—Eu1—N2 | 78.68 (8) | C13—C12—C11 | 120.1 (3) |
O1iii—Eu1—N2 | 78.59 (7) | C13—C12—H12 | 120.0 |
O7i—Eu1—N1 | 136.33 (8) | C11—C12—H12 | 120.0 |
O4—Eu1—N1 | 82.30 (7) | C14—C13—C12 | 118.4 (3) |
O6—Eu1—N1 | 139.26 (7) | C14—C13—H13 | 120.8 |
O5ii—Eu1—N1 | 74.33 (7) | C12—C13—H13 | 120.8 |
O1iii—Eu1—N1 | 65.59 (8) | C13—C14—C15 | 119.4 (3) |
N2—Eu1—N1 | 64.28 (7) | C13—C14—H14 | 120.3 |
O7i—Eu1—N3 | 73.63 (8) | C15—C14—H14 | 120.3 |
O4—Eu1—N3 | 147.24 (7) | N3—C15—C14 | 123.0 (3) |
O6—Eu1—N3 | 77.29 (7) | N3—C15—H15 | 118.5 |
O5ii—Eu1—N3 | 77.92 (8) | C14—C15—H15 | 118.5 |
O1iii—Eu1—N3 | 119.72 (8) | C17—C16—C21 | 118.7 (3) |
N2—Eu1—N3 | 63.41 (7) | C17—C16—C8 | 117.2 (3) |
N1—Eu1—N3 | 124.23 (8) | C21—C16—C8 | 124.1 (3) |
O3—S1—O2 | 115.50 (19) | C18—C17—C16 | 121.4 (3) |
O3—S1—O1 | 111.61 (15) | C18—C17—H17 | 119.3 |
O2—S1—O1 | 112.73 (16) | C16—C17—H17 | 119.3 |
O3—S1—C21 | 106.56 (16) | C19—C18—C17 | 119.7 (3) |
O2—S1—C21 | 105.18 (15) | C19—C18—H18 | 120.2 |
O1—S1—C21 | 104.17 (14) | C17—C18—H18 | 120.2 |
C1—N1—C5 | 118.5 (3) | C18—C19—C20 | 119.9 (3) |
C1—N1—Eu1 | 121.3 (2) | C18—C19—H19 | 120.1 |
C5—N1—Eu1 | 117.26 (19) | C20—C19—H19 | 120.1 |
C10—N2—C6 | 118.3 (2) | C21—C20—C19 | 121.0 (3) |
C10—N2—Eu1 | 122.67 (17) | C21—C20—H20 | 119.5 |
C6—N2—Eu1 | 119.01 (18) | C19—C20—H20 | 119.5 |
C11—N3—C15 | 118.1 (3) | C20—C21—C16 | 119.2 (3) |
C11—N3—Eu1 | 120.76 (18) | C20—C21—S1 | 120.3 (3) |
C15—N3—Eu1 | 121.1 (2) | C16—C21—S1 | 120.4 (2) |
S1—O1—Eu1iv | 147.33 (14) | O5—C22—O4 | 123.2 (3) |
C22—O4—Eu1 | 124.86 (18) | O5—C22—C23 | 118.2 (3) |
C22—O5—Eu1ii | 149.99 (19) | O4—C22—C23 | 118.6 (3) |
C29—O6—Eu1 | 128.43 (19) | C24—C23—C28 | 118.6 (3) |
C29—O7—Eu1i | 164.6 (2) | C24—C23—C22 | 118.2 (3) |
N1—C1—C2 | 123.2 (3) | C28—C23—C22 | 123.3 (3) |
N1—C1—H1 | 118.4 | C25—C24—C23 | 121.5 (3) |
C2—C1—H1 | 118.4 | C25—C24—H24 | 119.2 |
C3—C2—C1 | 118.1 (3) | C23—C24—H24 | 119.2 |
C3—C2—H2 | 120.9 | C26—C25—C24 | 119.8 (3) |
C1—C2—H2 | 120.9 | C26—C25—H25 | 120.1 |
C2—C3—C4 | 119.6 (3) | C24—C25—H25 | 120.1 |
C2—C3—H3 | 120.2 | C27—C26—C25 | 119.6 (3) |
C4—C3—H3 | 120.2 | C27—C26—H26 | 120.2 |
C3—C4—C5 | 119.5 (3) | C25—C26—H26 | 120.2 |
C3—C4—H4 | 120.3 | C26—C27—C28 | 121.4 (3) |
C5—C4—H4 | 120.3 | C26—C27—H27 | 119.3 |
N1—C5—C4 | 120.9 (3) | C28—C27—H27 | 119.3 |
N1—C5—C6 | 116.5 (2) | C27—C28—C23 | 119.2 (3) |
C4—C5—C6 | 122.5 (3) | C27—C28—C29 | 118.3 (3) |
N2—C6—C7 | 121.4 (3) | C23—C28—C29 | 122.5 (3) |
N2—C6—C5 | 116.9 (3) | O7—C29—O6 | 123.7 (3) |
C7—C6—C5 | 121.5 (3) | O7—C29—C28 | 118.3 (3) |
C6—C7—C8 | 120.2 (3) | O6—C29—C28 | 118.0 (3) |
C6—C7—H7 | 119.9 | | |
| | | |
O3—S1—O1—Eu1iv | −39.7 (3) | C9—C8—C16—C17 | −62.4 (4) |
O2—S1—O1—Eu1iv | 92.3 (3) | C7—C8—C16—C17 | 112.9 (3) |
C21—S1—O1—Eu1iv | −154.2 (3) | C9—C8—C16—C21 | 114.8 (4) |
C5—N1—C1—C2 | 0.7 (5) | C7—C8—C16—C21 | −70.0 (4) |
Eu1—N1—C1—C2 | −159.3 (3) | C21—C16—C17—C18 | −0.3 (5) |
N1—C1—C2—C3 | 2.6 (6) | C8—C16—C17—C18 | 177.0 (3) |
C1—C2—C3—C4 | −3.7 (7) | C16—C17—C18—C19 | −2.5 (5) |
C2—C3—C4—C5 | 1.8 (7) | C17—C18—C19—C20 | 2.7 (5) |
C1—N1—C5—C4 | −2.7 (5) | C18—C19—C20—C21 | −0.1 (5) |
Eu1—N1—C5—C4 | 158.1 (3) | C19—C20—C21—C16 | −2.8 (5) |
C1—N1—C5—C6 | 174.1 (3) | C19—C20—C21—S1 | 179.7 (3) |
Eu1—N1—C5—C6 | −25.2 (3) | C17—C16—C21—C20 | 2.9 (5) |
C3—C4—C5—N1 | 1.4 (6) | C8—C16—C21—C20 | −174.2 (3) |
C3—C4—C5—C6 | −175.1 (4) | C17—C16—C21—S1 | −179.6 (2) |
C10—N2—C6—C7 | 5.4 (4) | C8—C16—C21—S1 | 3.3 (4) |
Eu1—N2—C6—C7 | −173.5 (2) | O3—S1—C21—C20 | −120.8 (3) |
C10—N2—C6—C5 | −169.8 (3) | O2—S1—C21—C20 | 116.1 (3) |
Eu1—N2—C6—C5 | 11.3 (3) | O1—S1—C21—C20 | −2.7 (3) |
N1—C5—C6—N2 | 9.4 (4) | O3—S1—C21—C16 | 61.7 (3) |
C4—C5—C6—N2 | −173.9 (3) | O2—S1—C21—C16 | −61.4 (3) |
N1—C5—C6—C7 | −165.7 (3) | O1—S1—C21—C16 | 179.9 (2) |
C4—C5—C6—C7 | 11.0 (5) | Eu1ii—O5—C22—O4 | −116.2 (4) |
N2—C6—C7—C8 | −2.5 (5) | Eu1ii—O5—C22—C23 | 66.3 (5) |
C5—C6—C7—C8 | 172.3 (3) | Eu1—O4—C22—O5 | 80.8 (3) |
C6—C7—C8—C9 | −1.8 (5) | Eu1—O4—C22—C23 | −101.7 (3) |
C6—C7—C8—C16 | −177.2 (3) | O5—C22—C23—C24 | 48.2 (4) |
C7—C8—C9—C10 | 3.3 (5) | O4—C22—C23—C24 | −129.4 (3) |
C16—C8—C9—C10 | 178.9 (3) | O5—C22—C23—C28 | −132.5 (3) |
C6—N2—C10—C9 | −3.8 (4) | O4—C22—C23—C28 | 49.9 (4) |
Eu1—N2—C10—C9 | 175.0 (2) | C28—C23—C24—C25 | 0.7 (5) |
C6—N2—C10—C11 | 174.8 (3) | C22—C23—C24—C25 | −179.9 (3) |
Eu1—N2—C10—C11 | −6.3 (3) | C23—C24—C25—C26 | 0.7 (5) |
C8—C9—C10—N2 | −0.5 (5) | C24—C25—C26—C27 | −1.5 (5) |
C8—C9—C10—C11 | −179.1 (3) | C25—C26—C27—C28 | 0.8 (5) |
C15—N3—C11—C12 | −2.5 (5) | C26—C27—C28—C23 | 0.6 (5) |
Eu1—N3—C11—C12 | 179.5 (2) | C26—C27—C28—C29 | 178.2 (3) |
C15—N3—C11—C10 | 177.8 (3) | C24—C23—C28—C27 | −1.3 (4) |
Eu1—N3—C11—C10 | −0.2 (4) | C22—C23—C28—C27 | 179.3 (3) |
N2—C10—C11—N3 | 4.1 (4) | C24—C23—C28—C29 | −178.8 (3) |
C9—C10—C11—N3 | −177.2 (3) | C22—C23—C28—C29 | 1.9 (5) |
N2—C10—C11—C12 | −175.6 (3) | Eu1i—O7—C29—O6 | −128.2 (7) |
C9—C10—C11—C12 | 3.0 (5) | Eu1i—O7—C29—C28 | 53.4 (9) |
N3—C11—C12—C13 | 1.4 (5) | Eu1—O6—C29—O7 | 82.2 (3) |
C10—C11—C12—C13 | −178.9 (3) | Eu1—O6—C29—C28 | −99.4 (3) |
C11—C12—C13—C14 | 1.1 (6) | C27—C28—C29—O7 | 29.2 (4) |
C12—C13—C14—C15 | −2.4 (6) | C23—C28—C29—O7 | −153.3 (3) |
C11—N3—C15—C14 | 1.2 (5) | C27—C28—C29—O6 | −149.3 (3) |
Eu1—N3—C15—C14 | 179.1 (3) | C23—C28—C29—O6 | 28.2 (4) |
C13—C14—C15—N3 | 1.3 (6) | | |
Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y, −z; (iii) −x+1/2, y−1/2, −z+1/2; (iv) −x+1/2, y+1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···O6 | 0.93 | 2.40 | 3.034 (4) | 125 |
C1—H1···O4 | 0.93 | 2.58 | 3.173 (4) | 122 |
C15—H15···O6 | 0.93 | 2.40 | 3.034 (4) | 125 |
C1—H1···O4 | 0.93 | 2.58 | 3.173 (4) | 122 |
C1—H1···O4 | 0.93 | 2.58 | 3.173 (4) | 122 |
C15—H15···O6 | 0.93 | 2.40 | 3.034 (4) | 125 |
Crystal data top
C29H18N3O7STb | F(000) = 1400 |
Mr = 711.44 | Dx = 1.879 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.119 (1) Å | Cell parameters from 5396 reflections |
b = 13.4630 (15) Å | θ = 2.5–26.7° |
c = 20.674 (2) Å | µ = 2.95 mm−1 |
β = 97.756 (2)° | T = 296 K |
V = 2514.8 (5) Å3 | Block, yellow |
Z = 4 | 0.22 × 0.18 × 0.16 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 3901 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.027 |
Absorption correction: multi-scan sadabs | θmax = 25.1°, θmin = 2.0° |
Tmin = 0.533, Tmax = 0.625 | h = −10→10 |
12344 measured reflections | k = −15→15 |
4429 independent reflections | l = −10→24 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.022 | H-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 reflections | Δρmax = 0.47 e Å−3 |
370 parameters | Δρmin = −0.51 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Tb1 | 0.27704 (2) | 0.91890 (2) | 0.55400 (2) | 0.01927 (6) | |
S1 | 0.28374 (10) | 0.49291 (7) | 0.77860 (4) | 0.0339 (2) | |
N1 | 0.5138 (3) | 0.89674 (18) | 0.63338 (13) | 0.0236 (6) | |
N2 | 0.3318 (3) | 0.74370 (18) | 0.59182 (12) | 0.0219 (6) | |
N3 | 0.1464 (3) | 0.78131 (18) | 0.48184 (12) | 0.0260 (6) | |
O1 | 0.2576 (3) | 0.42859 (18) | 0.83338 (11) | 0.0376 (6) | |
O2 | 0.3915 (3) | 0.56879 (19) | 0.79881 (13) | 0.0567 (8) | |
O3 | 0.1486 (3) | 0.5273 (2) | 0.74090 (13) | 0.0601 (8) | |
O4 | 0.3509 (2) | 1.08309 (15) | 0.56182 (10) | 0.0257 (5) | |
O5 | 0.5405 (2) | 1.12528 (16) | 0.51044 (10) | 0.0281 (5) | |
O6 | 0.1957 (2) | 1.00117 (15) | 0.45648 (10) | 0.0247 (5) | |
O7 | −0.0307 (2) | 1.06443 (17) | 0.43899 (11) | 0.0314 (5) | |
C1 | 0.6037 (3) | 0.9724 (3) | 0.65144 (17) | 0.0313 (8) | |
H1 | 0.5972 | 1.0288 | 0.6253 | 0.038* | |
C2 | 0.7057 (4) | 0.9716 (3) | 0.7066 (2) | 0.0491 (11) | |
H2 | 0.7691 | 1.0252 | 0.7169 | 0.059* | |
C3 | 0.7116 (5) | 0.8902 (3) | 0.7460 (2) | 0.0628 (14) | |
H3 | 0.7768 | 0.8886 | 0.7847 | 0.075* | |
C4 | 0.6210 (4) | 0.8105 (3) | 0.72836 (19) | 0.0482 (11) | |
H4 | 0.6253 | 0.7543 | 0.7547 | 0.058* | |
C5 | 0.5238 (3) | 0.8143 (2) | 0.67129 (15) | 0.0252 (7) | |
C6 | 0.4321 (3) | 0.7282 (2) | 0.64597 (15) | 0.0233 (7) | |
C7 | 0.4566 (3) | 0.6341 (2) | 0.67247 (15) | 0.0269 (7) | |
H7 | 0.5233 | 0.6253 | 0.7102 | 0.032* | |
C8 | 0.3818 (3) | 0.5530 (2) | 0.64268 (15) | 0.0252 (7) | |
C9 | 0.2881 (3) | 0.5693 (2) | 0.58528 (16) | 0.0266 (7) | |
H9 | 0.2409 | 0.5159 | 0.5629 | 0.032* | |
C10 | 0.2639 (3) | 0.6648 (2) | 0.56081 (14) | 0.0234 (7) | |
C11 | 0.1650 (3) | 0.6850 (2) | 0.49866 (15) | 0.0234 (7) | |
C12 | 0.0964 (4) | 0.6096 (3) | 0.46006 (18) | 0.0381 (9) | |
H12 | 0.1128 | 0.5436 | 0.4723 | 0.046* | |
C13 | 0.0038 (4) | 0.6323 (3) | 0.40355 (18) | 0.0416 (9) | |
H13 | −0.0413 | 0.5824 | 0.3768 | 0.050* | |
C14 | −0.0200 (4) | 0.7311 (3) | 0.38779 (18) | 0.0418 (9) | |
H14 | −0.0848 | 0.7492 | 0.3510 | 0.050* | |
C15 | 0.0537 (4) | 0.8026 (3) | 0.42731 (17) | 0.0346 (8) | |
H15 | 0.0386 | 0.8690 | 0.4157 | 0.042* | |
C16 | 0.4085 (3) | 0.4486 (2) | 0.66687 (15) | 0.0254 (7) | |
C17 | 0.4740 (4) | 0.3834 (3) | 0.62709 (17) | 0.0336 (8) | |
H17 | 0.5034 | 0.4070 | 0.5886 | 0.040* | |
C18 | 0.4964 (4) | 0.2844 (3) | 0.64344 (18) | 0.0387 (9) | |
H18 | 0.5439 | 0.2426 | 0.6171 | 0.046* | |
C19 | 0.4477 (4) | 0.2486 (3) | 0.69914 (18) | 0.0421 (9) | |
H19 | 0.4580 | 0.1815 | 0.7095 | 0.051* | |
C20 | 0.3833 (4) | 0.3122 (2) | 0.73981 (17) | 0.0355 (8) | |
H20 | 0.3515 | 0.2873 | 0.7775 | 0.043* | |
C21 | 0.3654 (3) | 0.4124 (2) | 0.72516 (15) | 0.0266 (7) | |
C22 | 0.4061 (3) | 1.1305 (2) | 0.51841 (15) | 0.0230 (7) | |
C23 | 0.3092 (3) | 1.2023 (2) | 0.47531 (15) | 0.0224 (7) | |
C24 | 0.3608 (4) | 1.2985 (2) | 0.46803 (17) | 0.0305 (8) | |
H24 | 0.4526 | 1.3170 | 0.4898 | 0.037* | |
C25 | 0.2777 (4) | 1.3668 (3) | 0.42897 (19) | 0.0392 (9) | |
H25 | 0.3135 | 1.4309 | 0.4252 | 0.047* | |
C26 | 0.1418 (4) | 1.3405 (3) | 0.39552 (19) | 0.0435 (10) | |
H26 | 0.0870 | 1.3859 | 0.3682 | 0.052* | |
C27 | 0.0886 (4) | 1.2460 (3) | 0.40317 (17) | 0.0352 (8) | |
H27 | −0.0038 | 1.2287 | 0.3814 | 0.042* | |
C28 | 0.1694 (3) | 1.1757 (2) | 0.44265 (15) | 0.0249 (7) | |
C29 | 0.1068 (3) | 1.0733 (2) | 0.44688 (15) | 0.0232 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Tb1 | 0.01796 (9) | 0.01908 (9) | 0.02058 (9) | 0.00035 (6) | 0.00197 (6) | 0.00155 (7) |
S1 | 0.0415 (5) | 0.0356 (5) | 0.0262 (5) | 0.0004 (4) | 0.0101 (4) | 0.0008 (4) |
N1 | 0.0236 (14) | 0.0245 (14) | 0.0230 (14) | −0.0011 (11) | 0.0047 (11) | −0.0023 (12) |
N2 | 0.0213 (13) | 0.0238 (14) | 0.0202 (14) | −0.0002 (11) | 0.0012 (11) | 0.0026 (12) |
N3 | 0.0299 (15) | 0.0228 (15) | 0.0235 (14) | 0.0011 (11) | −0.0030 (12) | 0.0025 (12) |
O1 | 0.0373 (14) | 0.0520 (16) | 0.0245 (13) | −0.0091 (11) | 0.0082 (11) | 0.0034 (12) |
O2 | 0.086 (2) | 0.0462 (17) | 0.0434 (17) | −0.0274 (15) | 0.0304 (15) | −0.0157 (14) |
O3 | 0.0606 (19) | 0.076 (2) | 0.0446 (17) | 0.0347 (16) | 0.0095 (14) | 0.0041 (16) |
O4 | 0.0306 (12) | 0.0225 (12) | 0.0238 (12) | −0.0053 (9) | 0.0032 (9) | 0.0021 (10) |
O5 | 0.0227 (12) | 0.0356 (13) | 0.0261 (12) | 0.0054 (10) | 0.0031 (10) | −0.0017 (10) |
O6 | 0.0246 (11) | 0.0238 (12) | 0.0255 (12) | 0.0006 (9) | 0.0026 (9) | 0.0018 (10) |
O7 | 0.0185 (12) | 0.0404 (14) | 0.0348 (14) | −0.0010 (10) | 0.0018 (10) | 0.0032 (11) |
C1 | 0.0267 (18) | 0.0306 (19) | 0.037 (2) | −0.0026 (15) | 0.0038 (15) | 0.0022 (16) |
C2 | 0.039 (2) | 0.036 (2) | 0.066 (3) | −0.0114 (17) | −0.021 (2) | −0.001 (2) |
C3 | 0.066 (3) | 0.048 (3) | 0.060 (3) | −0.008 (2) | −0.043 (2) | 0.004 (2) |
C4 | 0.062 (3) | 0.036 (2) | 0.039 (2) | −0.0028 (19) | −0.022 (2) | 0.0065 (18) |
C5 | 0.0272 (17) | 0.0223 (17) | 0.0251 (18) | 0.0014 (13) | −0.0004 (14) | −0.0024 (14) |
C6 | 0.0249 (16) | 0.0269 (18) | 0.0184 (16) | 0.0000 (13) | 0.0034 (13) | −0.0010 (14) |
C7 | 0.0304 (18) | 0.0292 (18) | 0.0196 (17) | 0.0036 (14) | −0.0016 (14) | 0.0041 (14) |
C8 | 0.0299 (18) | 0.0242 (17) | 0.0227 (17) | 0.0025 (13) | 0.0081 (14) | 0.0017 (14) |
C9 | 0.0321 (18) | 0.0222 (18) | 0.0246 (17) | −0.0048 (14) | 0.0010 (14) | −0.0004 (14) |
C10 | 0.0231 (16) | 0.0258 (17) | 0.0219 (17) | −0.0008 (13) | 0.0055 (13) | 0.0023 (14) |
C11 | 0.0240 (16) | 0.0247 (17) | 0.0209 (17) | −0.0003 (13) | 0.0012 (13) | 0.0015 (14) |
C12 | 0.048 (2) | 0.0252 (19) | 0.038 (2) | −0.0050 (16) | −0.0064 (18) | 0.0025 (16) |
C13 | 0.051 (2) | 0.033 (2) | 0.036 (2) | −0.0087 (17) | −0.0132 (18) | −0.0040 (17) |
C14 | 0.046 (2) | 0.038 (2) | 0.035 (2) | −0.0032 (17) | −0.0158 (17) | 0.0010 (18) |
C15 | 0.040 (2) | 0.0282 (19) | 0.032 (2) | −0.0034 (15) | −0.0083 (16) | 0.0021 (16) |
C16 | 0.0278 (17) | 0.0229 (17) | 0.0236 (18) | −0.0002 (13) | −0.0035 (14) | 0.0023 (14) |
C17 | 0.045 (2) | 0.0327 (19) | 0.0228 (18) | 0.0015 (16) | 0.0047 (16) | 0.0008 (15) |
C18 | 0.048 (2) | 0.030 (2) | 0.037 (2) | 0.0026 (16) | 0.0020 (18) | −0.0118 (17) |
C19 | 0.053 (2) | 0.0230 (19) | 0.048 (2) | 0.0000 (17) | −0.0026 (19) | 0.0022 (18) |
C20 | 0.046 (2) | 0.030 (2) | 0.030 (2) | −0.0014 (16) | 0.0000 (17) | 0.0112 (16) |
C21 | 0.0283 (17) | 0.0287 (18) | 0.0218 (17) | −0.0016 (14) | −0.0006 (14) | 0.0017 (15) |
C22 | 0.0241 (17) | 0.0212 (16) | 0.0232 (17) | −0.0011 (13) | 0.0010 (14) | −0.0076 (14) |
C23 | 0.0228 (16) | 0.0215 (17) | 0.0243 (17) | 0.0016 (13) | 0.0083 (13) | −0.0006 (14) |
C24 | 0.0317 (19) | 0.0276 (19) | 0.034 (2) | −0.0003 (14) | 0.0118 (16) | −0.0019 (15) |
C25 | 0.047 (2) | 0.0208 (19) | 0.054 (3) | 0.0046 (16) | 0.024 (2) | 0.0080 (17) |
C26 | 0.046 (2) | 0.033 (2) | 0.052 (2) | 0.0127 (18) | 0.0116 (19) | 0.0209 (19) |
C27 | 0.0287 (18) | 0.038 (2) | 0.039 (2) | 0.0068 (16) | 0.0039 (16) | 0.0113 (18) |
C28 | 0.0235 (16) | 0.0289 (18) | 0.0237 (17) | 0.0051 (14) | 0.0079 (13) | 0.0013 (14) |
C29 | 0.0221 (17) | 0.0306 (18) | 0.0167 (16) | −0.0012 (14) | 0.0024 (13) | −0.0003 (14) |
Geometric parameters (Å, º) top
Tb1—O7i | 2.281 (2) | C7—H7 | 0.9300 |
Tb1—O4 | 2.310 (2) | C8—C9 | 1.383 (4) |
Tb1—O6 | 2.332 (2) | C8—C16 | 1.501 (4) |
Tb1—O5ii | 2.344 (2) | C9—C10 | 1.388 (4) |
Tb1—O1iii | 2.395 (2) | C9—H9 | 0.9300 |
Tb1—N2 | 2.514 (2) | C10—C11 | 1.492 (4) |
Tb1—N1 | 2.547 (3) | C11—C12 | 1.387 (4) |
Tb1—N3 | 2.568 (3) | C12—C13 | 1.380 (5) |
S1—O2 | 1.440 (3) | C12—H12 | 0.9300 |
S1—O3 | 1.442 (3) | C13—C14 | 1.380 (5) |
S1—O1 | 1.470 (2) | C13—H13 | 0.9300 |
S1—C21 | 1.781 (3) | C14—C15 | 1.377 (5) |
N1—C1 | 1.329 (4) | C14—H14 | 0.9300 |
N1—C5 | 1.355 (4) | C15—H15 | 0.9300 |
N2—C10 | 1.347 (4) | C16—C17 | 1.391 (5) |
N2—C6 | 1.363 (4) | C16—C21 | 1.405 (4) |
N3—C15 | 1.346 (4) | C17—C18 | 1.384 (5) |
N3—C11 | 1.347 (4) | C17—H17 | 0.9300 |
O1—Tb1iv | 2.395 (2) | C18—C19 | 1.376 (5) |
O4—C22 | 1.260 (4) | C18—H18 | 0.9300 |
O5—C22 | 1.260 (4) | C19—C20 | 1.385 (5) |
O5—Tb1ii | 2.344 (2) | C19—H19 | 0.9300 |
O6—C29 | 1.263 (4) | C20—C21 | 1.387 (4) |
O7—C29 | 1.249 (4) | C20—H20 | 0.9300 |
O7—Tb1i | 2.281 (2) | C22—C23 | 1.515 (4) |
C1—C2 | 1.371 (5) | C23—C24 | 1.392 (4) |
C1—H1 | 0.9300 | C23—C28 | 1.406 (4) |
C2—C3 | 1.362 (6) | C24—C25 | 1.381 (5) |
C2—H2 | 0.9300 | C24—H24 | 0.9300 |
C3—C4 | 1.374 (5) | C25—C26 | 1.381 (5) |
C3—H3 | 0.9300 | C25—H25 | 0.9300 |
C4—C5 | 1.378 (4) | C26—C27 | 1.379 (5) |
C4—H4 | 0.9300 | C26—H26 | 0.9300 |
C5—C6 | 1.483 (4) | C27—C28 | 1.394 (4) |
C6—C7 | 1.387 (4) | C27—H27 | 0.9300 |
C7—C8 | 1.387 (4) | C28—C29 | 1.499 (4) |
| | | |
O7i—Tb1—O4 | 100.47 (8) | C8—C7—H7 | 120.0 |
O7i—Tb1—O6 | 78.87 (8) | C9—C8—C7 | 117.8 (3) |
O4—Tb1—O6 | 70.23 (7) | C9—C8—C16 | 119.3 (3) |
O7i—Tb1—O5ii | 147.30 (8) | C7—C8—C16 | 122.8 (3) |
O4—Tb1—O5ii | 93.43 (8) | C8—C9—C10 | 120.6 (3) |
O6—Tb1—O5ii | 78.27 (7) | C8—C9—H9 | 119.7 |
O7i—Tb1—O1iii | 70.91 (8) | C10—C9—H9 | 119.7 |
O4—Tb1—O1iii | 87.44 (8) | N2—C10—C9 | 121.1 (3) |
O6—Tb1—O1iii | 138.27 (7) | N2—C10—C11 | 116.9 (3) |
O5ii—Tb1—O1iii | 139.73 (8) | C9—C10—C11 | 122.0 (3) |
O7i—Tb1—N2 | 103.20 (8) | N3—C11—C12 | 121.7 (3) |
O4—Tb1—N2 | 146.34 (8) | N3—C11—C10 | 116.0 (3) |
O6—Tb1—N2 | 137.84 (8) | C12—C11—C10 | 122.4 (3) |
O5ii—Tb1—N2 | 79.19 (8) | C13—C12—C11 | 120.1 (3) |
O1iii—Tb1—N2 | 78.19 (8) | C13—C12—H12 | 120.0 |
O7i—Tb1—N1 | 136.62 (8) | C11—C12—H12 | 120.0 |
O4—Tb1—N1 | 81.55 (8) | C14—C13—C12 | 118.2 (3) |
O6—Tb1—N1 | 139.10 (8) | C14—C13—H13 | 120.9 |
O5ii—Tb1—N1 | 74.43 (8) | C12—C13—H13 | 120.9 |
O1iii—Tb1—N1 | 65.88 (8) | C15—C14—C13 | 119.0 (3) |
N2—Tb1—N1 | 64.80 (8) | C15—C14—H14 | 120.5 |
O7i—Tb1—N3 | 74.00 (8) | C13—C14—H14 | 120.5 |
O4—Tb1—N3 | 147.01 (8) | N3—C15—C14 | 123.3 (3) |
O6—Tb1—N3 | 76.81 (8) | N3—C15—H15 | 118.4 |
O5ii—Tb1—N3 | 78.24 (8) | C14—C15—H15 | 118.4 |
O1iii—Tb1—N3 | 119.49 (8) | C17—C16—C21 | 118.7 (3) |
N2—Tb1—N3 | 63.96 (8) | C17—C16—C8 | 117.2 (3) |
N1—Tb1—N3 | 125.18 (8) | C21—C16—C8 | 124.0 (3) |
O2—S1—O3 | 115.39 (19) | C18—C17—C16 | 121.6 (3) |
O2—S1—O1 | 111.70 (16) | C18—C17—H17 | 119.2 |
O3—S1—O1 | 112.94 (17) | C16—C17—H17 | 119.2 |
O2—S1—C21 | 106.61 (16) | C19—C18—C17 | 119.2 (3) |
O3—S1—C21 | 104.98 (16) | C19—C18—H18 | 120.4 |
O1—S1—C21 | 104.12 (15) | C17—C18—H18 | 120.4 |
C1—N1—C5 | 118.3 (3) | C18—C19—C20 | 120.2 (3) |
C1—N1—Tb1 | 121.9 (2) | C18—C19—H19 | 119.9 |
C5—N1—Tb1 | 116.99 (19) | C20—C19—H19 | 119.9 |
C10—N2—C6 | 119.0 (3) | C19—C20—C21 | 121.0 (3) |
C10—N2—Tb1 | 122.17 (19) | C19—C20—H20 | 119.5 |
C6—N2—Tb1 | 118.85 (19) | C21—C20—H20 | 119.5 |
C15—N3—C11 | 117.7 (3) | C20—C21—C16 | 119.1 (3) |
C15—N3—Tb1 | 121.5 (2) | C20—C21—S1 | 120.2 (3) |
C11—N3—Tb1 | 120.8 (2) | C16—C21—S1 | 120.7 (2) |
S1—O1—Tb1iv | 146.84 (15) | O5—C22—O4 | 123.6 (3) |
C22—O4—Tb1 | 125.14 (19) | O5—C22—C23 | 117.3 (3) |
C22—O5—Tb1ii | 150.0 (2) | O4—C22—C23 | 119.0 (3) |
C29—O6—Tb1 | 128.58 (19) | C24—C23—C28 | 118.8 (3) |
C29—O7—Tb1i | 164.3 (2) | C24—C23—C22 | 118.6 (3) |
N1—C1—C2 | 123.5 (3) | C28—C23—C22 | 122.6 (3) |
N1—C1—H1 | 118.2 | C25—C24—C23 | 121.1 (3) |
C2—C1—H1 | 118.2 | C25—C24—H24 | 119.5 |
C3—C2—C1 | 118.1 (3) | C23—C24—H24 | 119.5 |
C3—C2—H2 | 121.0 | C24—C25—C26 | 120.4 (3) |
C1—C2—H2 | 121.0 | C24—C25—H25 | 119.8 |
C2—C3—C4 | 119.8 (4) | C26—C25—H25 | 119.8 |
C2—C3—H3 | 120.1 | C27—C26—C25 | 119.0 (3) |
C4—C3—H3 | 120.1 | C27—C26—H26 | 120.5 |
C3—C4—C5 | 119.5 (4) | C25—C26—H26 | 120.5 |
C3—C4—H4 | 120.2 | C26—C27—C28 | 121.8 (3) |
C5—C4—H4 | 120.2 | C26—C27—H27 | 119.1 |
N1—C5—C4 | 120.7 (3) | C28—C27—H27 | 119.1 |
N1—C5—C6 | 116.5 (3) | C27—C28—C23 | 118.8 (3) |
C4—C5—C6 | 122.7 (3) | C27—C28—C29 | 118.9 (3) |
N2—C6—C7 | 121.3 (3) | C23—C28—C29 | 122.3 (3) |
N2—C6—C5 | 117.0 (3) | O7—C29—O6 | 124.0 (3) |
C7—C6—C5 | 121.5 (3) | O7—C29—C28 | 117.7 (3) |
C6—C7—C8 | 120.0 (3) | O6—C29—C28 | 118.4 (3) |
C6—C7—H7 | 120.0 | | |
| | | |
O2—S1—O1—Tb1iv | 41.9 (3) | C9—C8—C16—C17 | 61.9 (4) |
O3—S1—O1—Tb1iv | −90.2 (3) | C7—C8—C16—C17 | −112.5 (4) |
C21—S1—O1—Tb1iv | 156.5 (2) | C9—C8—C16—C21 | −115.1 (4) |
C5—N1—C1—C2 | −0.4 (5) | C7—C8—C16—C21 | 70.5 (4) |
Tb1—N1—C1—C2 | 160.2 (3) | C21—C16—C17—C18 | 0.4 (5) |
N1—C1—C2—C3 | −2.2 (6) | C8—C16—C17—C18 | −176.7 (3) |
C1—C2—C3—C4 | 2.7 (7) | C16—C17—C18—C19 | 2.5 (5) |
C2—C3—C4—C5 | −0.8 (7) | C17—C18—C19—C20 | −3.0 (5) |
C1—N1—C5—C4 | 2.4 (5) | C18—C19—C20—C21 | 0.6 (5) |
Tb1—N1—C5—C4 | −159.2 (3) | C19—C20—C21—C16 | 2.4 (5) |
C1—N1—C5—C6 | −174.1 (3) | C19—C20—C21—S1 | −179.4 (3) |
Tb1—N1—C5—C6 | 24.4 (3) | C17—C16—C21—C20 | −2.8 (5) |
C3—C4—C5—N1 | −1.8 (6) | C8—C16—C21—C20 | 174.0 (3) |
C3—C4—C5—C6 | 174.4 (4) | C17—C16—C21—S1 | 179.0 (2) |
C10—N2—C6—C7 | −5.2 (4) | C8—C16—C21—S1 | −4.1 (4) |
Tb1—N2—C6—C7 | 174.0 (2) | O2—S1—C21—C20 | 121.1 (3) |
C10—N2—C6—C5 | 169.0 (3) | O3—S1—C21—C20 | −116.1 (3) |
Tb1—N2—C6—C5 | −11.7 (3) | O1—S1—C21—C20 | 2.8 (3) |
N1—C5—C6—N2 | −8.7 (4) | O2—S1—C21—C16 | −60.8 (3) |
C4—C5—C6—N2 | 174.9 (3) | O3—S1—C21—C16 | 62.1 (3) |
N1—C5—C6—C7 | 165.5 (3) | O1—S1—C21—C16 | −179.0 (3) |
C4—C5—C6—C7 | −10.9 (5) | Tb1ii—O5—C22—O4 | 115.5 (4) |
N2—C6—C7—C8 | 2.0 (5) | Tb1ii—O5—C22—C23 | −67.9 (5) |
C5—C6—C7—C8 | −171.9 (3) | Tb1—O4—C22—O5 | −81.4 (3) |
C6—C7—C8—C9 | 2.4 (5) | Tb1—O4—C22—C23 | 102.0 (3) |
C6—C7—C8—C16 | 176.9 (3) | O5—C22—C23—C24 | −47.2 (4) |
C7—C8—C9—C10 | −3.7 (5) | O4—C22—C23—C24 | 129.6 (3) |
C16—C8—C9—C10 | −178.4 (3) | O5—C22—C23—C28 | 133.0 (3) |
C6—N2—C10—C9 | 3.8 (4) | O4—C22—C23—C28 | −50.2 (4) |
Tb1—N2—C10—C9 | −175.4 (2) | C28—C23—C24—C25 | −0.7 (5) |
C6—N2—C10—C11 | −174.9 (3) | C22—C23—C24—C25 | 179.5 (3) |
Tb1—N2—C10—C11 | 5.9 (3) | C23—C24—C25—C26 | −0.8 (5) |
C8—C9—C10—N2 | 0.6 (5) | C24—C25—C26—C27 | 1.8 (6) |
C8—C9—C10—C11 | 179.3 (3) | C25—C26—C27—C28 | −1.3 (6) |
C15—N3—C11—C12 | 2.7 (5) | C26—C27—C28—C23 | −0.2 (5) |
Tb1—N3—C11—C12 | −179.4 (3) | C26—C27—C28—C29 | −178.0 (3) |
C15—N3—C11—C10 | −177.6 (3) | C24—C23—C28—C27 | 1.2 (5) |
Tb1—N3—C11—C10 | 0.2 (4) | C22—C23—C28—C27 | −179.0 (3) |
N2—C10—C11—N3 | −3.9 (4) | C24—C23—C28—C29 | 178.9 (3) |
C9—C10—C11—N3 | 177.4 (3) | C22—C23—C28—C29 | −1.3 (5) |
N2—C10—C11—C12 | 175.8 (3) | Tb1i—O7—C29—O6 | 129.9 (7) |
C9—C10—C11—C12 | −2.9 (5) | Tb1i—O7—C29—C28 | −52.0 (9) |
N3—C11—C12—C13 | −1.5 (5) | Tb1—O6—C29—O7 | −82.5 (4) |
C10—C11—C12—C13 | 178.9 (3) | Tb1—O6—C29—C28 | 99.4 (3) |
C11—C12—C13—C14 | −1.2 (6) | C27—C28—C29—O7 | −29.0 (4) |
C12—C13—C14—C15 | 2.6 (6) | C23—C28—C29—O7 | 153.3 (3) |
C11—N3—C15—C14 | −1.2 (5) | C27—C28—C29—O6 | 149.2 (3) |
Tb1—N3—C15—C14 | −179.1 (3) | C23—C28—C29—O6 | −28.5 (4) |
C13—C14—C15—N3 | −1.4 (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, y−1/2, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···O6 | 0.93 | 2.37 | 2.996 (4) | 125 |
C1—H1···O4 | 0.93 | 2.55 | 3.133 (4) | 121 |