Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010400366X/gd1306sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010400366X/gd1306Isup2.hkl |
CCDC reference: 237911
IsoamylCbl was prepared by a method similar to that used to prepare MeCbl (Brown et al., 1997). CNCbl (50 mg) was dissolved in a methanol solution (40 ml) containing a 10%(v/v) acetic acid solution (10 ml). After purging the solution with argon for 40 min, zinc wool was added in excess. The reduction process was accompanied by a change in colour from red to brown and was monitored by high-pressure liquid chromatography (HPLC). Once the reduction process had been completed, a 100-fold excess of redistilled 1-bromo-3-methyl butane dissolved in deaerated methanol was transferred by canula into the reduced cobalamin solution in a darkroom, working only under dim red light. Formation of the product was again monitored by HPLC, and on completion of the reaction, the solution was transferred by canula into an empty vessel and exposed to air. The solution was then desalted on a 6 ml ISOLUTE SPE C18(EC) column and rotary-evaporated (303 K) to dryness in the dark. The isoamylCbl solution was redissolved in a minimal amount of deionized water. Crystals were grown in H tubes in a refrigerator, by vapour diffusion of acetone into the aqueous solution. Crystals appeared after about two weeks.
H atoms were positioned geometrically and allowed to ride on their respective parent atoms, with C—H distances of 0.98–1.00 Å, N—H distances of 0.88 Å and O—H distances of 0.84–0.93 Å, and with Uiso(H) equal to 1.2Ueq(C) [1.5Ueq(C) for methyl groups]. The structure contains eleven ordered water molecules, one disordered water molecule and two water molecules that were assigned partial occupancy. In addition, there is a solvent acetone molecule that was assigned partial occupancy (site occupancy 0.385). No elemental analyses were performed, as these have been found to be unreliable with respect to the water content. The upper axial isoamyl group was found to be disordered and was refined over two positions, with the final occupancies over the two positions being 0.615 (4) and 0.385 (4), respectively.
Data collection: SMART (Bruker,1998); cell refinement: SMART; data reduction: SAINT (Bruker,1999); program(s) used to solve structure: SHELXTL (Bruker,1999); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia,1997); software used to prepare material for publication: SHELXTL.
[Co(C5H11)(C62H88N13O14P)]·0.385C3H6O·12.650H2O | F(000) = 3539 |
Mr = 1650.69 | Dx = 1.354 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1015 reflections |
a = 15.959 (3) Å | θ = 3.0–26.5° |
b = 20.793 (4) Å | µ = 0.32 mm−1 |
c = 24.403 (5) Å | T = 123 K |
V = 8098 (3) Å3 | Rectangular, dark red |
Z = 4 | 0.48 × 0.26 × 0.26 mm |
Bruker SMART CCD area-detector diffractometer | 14388 reflections with I > 2σ(I) |
ϕ and ω scans | Rint = 0.031 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 26.5°, θmin = 1.3° |
Tmin = 0.863, Tmax = 0.922 | h = −20→19 |
45443 measured reflections | k = −17→26 |
16502 independent reflections | l = −30→30 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.052P)2 + 5.1666P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.002 |
16502 reflections | Δρmax = 0.59 e Å−3 |
1085 parameters | Δρmin = −0.44 e Å−3 |
45 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881, 7369 Friedel pairs. |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.010 (10) |
[Co(C5H11)(C62H88N13O14P)]·0.385C3H6O·12.650H2O | V = 8098 (3) Å3 |
Mr = 1650.69 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 15.959 (3) Å | µ = 0.32 mm−1 |
b = 20.793 (4) Å | T = 123 K |
c = 24.403 (5) Å | 0.48 × 0.26 × 0.26 mm |
Bruker SMART CCD area-detector diffractometer | 16502 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 14388 reflections with I > 2σ(I) |
Tmin = 0.863, Tmax = 0.922 | Rint = 0.031 |
45443 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.107 | Δρmax = 0.59 e Å−3 |
S = 1.05 | Δρmin = −0.44 e Å−3 |
16502 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881, 7369 Friedel pairs. |
1085 parameters | Absolute structure parameter: 0.010 (10) |
45 restraints |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.63334 (17) | 0.21189 (13) | 0.76263 (11) | 0.0148 (6) | |
C2 | 0.53670 (17) | 0.22198 (13) | 0.75104 (11) | 0.0155 (6) | |
C3 | 0.50596 (17) | 0.15100 (13) | 0.74537 (11) | 0.0165 (6) | |
H3 | 0.4606 | 0.1495 | 0.7172 | 0.02* | |
C4 | 0.58364 (16) | 0.11845 (13) | 0.72198 (10) | 0.0147 (6) | |
C5 | 0.58131 (17) | 0.05684 (13) | 0.69391 (11) | 0.0162 (6) | |
C6 | 0.65307 (17) | 0.02419 (13) | 0.68262 (11) | 0.0153 (6) | |
C7 | 0.66304 (18) | −0.04396 (13) | 0.65751 (11) | 0.0174 (6) | |
C8 | 0.75190 (17) | −0.06203 (13) | 0.67907 (11) | 0.0176 (6) | |
H8 | 0.7821 | −0.0896 | 0.6519 | 0.021* | |
C9 | 0.79170 (17) | 0.00327 (13) | 0.68253 (11) | 0.0161 (6) | |
C10 | 0.87671 (18) | 0.01328 (14) | 0.67563 (12) | 0.0188 (6) | |
H10 | 0.91 | −0.0228 | 0.6656 | 0.023* | |
C11 | 0.91710 (17) | 0.07161 (13) | 0.68213 (11) | 0.0155 (6) | |
C12 | 1.00924 (17) | 0.08189 (13) | 0.66868 (12) | 0.0174 (6) | |
C13 | 1.02776 (16) | 0.14324 (13) | 0.70301 (11) | 0.0170 (6) | |
H13 | 1.0658 | 0.1728 | 0.6823 | 0.02* | |
C14 | 0.94025 (17) | 0.17313 (13) | 0.70849 (11) | 0.0168 (6) | |
C15 | 0.92664 (17) | 0.23561 (13) | 0.72407 (11) | 0.0163 (6) | |
C16 | 0.84297 (17) | 0.25880 (13) | 0.73539 (10) | 0.0140 (5) | |
C17 | 0.81865 (17) | 0.32917 (13) | 0.74750 (11) | 0.0157 (6) | |
C18 | 0.72669 (17) | 0.32029 (12) | 0.76782 (11) | 0.0158 (6) | |
H18 | 0.7284 | 0.3102 | 0.8079 | 0.019* | |
C19 | 0.69816 (16) | 0.25944 (13) | 0.73736 (11) | 0.0148 (5) | |
H19 | 0.6786 | 0.272 | 0.6999 | 0.018* | |
C20 | 0.65419 (17) | 0.20274 (13) | 0.82355 (11) | 0.0153 (6) | |
H20A | 0.6277 | 0.1632 | 0.8369 | 0.023* | |
H20B | 0.6332 | 0.2396 | 0.8445 | 0.023* | |
H20C | 0.7151 | 0.1995 | 0.8281 | 0.023* | |
C21 | 0.49233 (17) | 0.26036 (13) | 0.79588 (12) | 0.0187 (6) | |
H21A | 0.5201 | 0.302 | 0.8005 | 0.028* | |
H21B | 0.4947 | 0.2364 | 0.8304 | 0.028* | |
H21C | 0.4337 | 0.2672 | 0.7855 | 0.028* | |
C22 | 0.52404 (17) | 0.25487 (14) | 0.69420 (12) | 0.0192 (6) | |
H22A | 0.543 | 0.3001 | 0.6968 | 0.023* | |
H22B | 0.5601 | 0.233 | 0.667 | 0.023* | |
C23 | 0.43386 (18) | 0.25410 (14) | 0.67337 (12) | 0.0224 (6) | |
C24 | 0.47476 (17) | 0.11536 (13) | 0.79772 (12) | 0.0178 (6) | |
H24A | 0.4855 | 0.0687 | 0.7935 | 0.021* | |
H24B | 0.5073 | 0.1307 | 0.8297 | 0.021* | |
C25 | 0.38098 (17) | 0.12589 (14) | 0.80884 (12) | 0.0211 (6) | |
H25A | 0.3715 | 0.1714 | 0.819 | 0.025* | |
H25B | 0.3489 | 0.1171 | 0.7749 | 0.025* | |
C26 | 0.34909 (19) | 0.08288 (16) | 0.85427 (13) | 0.0251 (7) | |
C27 | 0.49416 (19) | 0.03306 (15) | 0.67825 (14) | 0.0258 (7) | |
H27A | 0.4991 | −0.0016 | 0.6513 | 0.039* | |
H27B | 0.4619 | 0.0686 | 0.6625 | 0.039* | |
H27C | 0.4655 | 0.0169 | 0.711 | 0.039* | |
C28 | 0.59835 (19) | −0.09515 (14) | 0.67364 (13) | 0.0223 (6) | |
H28A | 0.5864 | −0.0918 | 0.7129 | 0.033* | |
H28B | 0.6207 | −0.138 | 0.6655 | 0.033* | |
H28C | 0.5466 | −0.0883 | 0.6528 | 0.033* | |
C29 | 0.67263 (19) | −0.04022 (14) | 0.59381 (12) | 0.0201 (6) | |
H29A | 0.7298 | −0.0244 | 0.5856 | 0.024* | |
H29B | 0.6686 | −0.0845 | 0.5791 | 0.024* | |
C30 | 0.61064 (19) | 0.00153 (15) | 0.56262 (12) | 0.0220 (6) | |
C31 | 0.75121 (18) | −0.09449 (13) | 0.73680 (11) | 0.0205 (6) | |
H31A | 0.7096 | −0.0723 | 0.7602 | 0.025* | |
H31B | 0.7331 | −0.1398 | 0.7328 | 0.025* | |
C32 | 0.83668 (18) | −0.09298 (15) | 0.76536 (12) | 0.0223 (6) | |
H32A | 0.8773 | −0.1162 | 0.7419 | 0.027* | |
H32B | 0.8553 | −0.0476 | 0.7674 | 0.027* | |
C33 | 0.84156 (19) | −0.12103 (14) | 0.82183 (12) | 0.0229 (6) | |
C34 | 1.0166 (2) | 0.09901 (16) | 0.60772 (12) | 0.0248 (7) | |
H34A | 0.992 | 0.0645 | 0.5856 | 0.037* | |
H34B | 1.0758 | 0.1042 | 0.598 | 0.037* | |
H34C | 0.9866 | 0.1393 | 0.6006 | 0.037* | |
C35 | 1.06333 (19) | 0.02276 (14) | 0.68084 (13) | 0.0237 (7) | |
H35A | 1.0556 | 0.0099 | 0.7191 | 0.035* | |
H35B | 1.1224 | 0.0332 | 0.6744 | 0.035* | |
H35C | 1.0466 | −0.0127 | 0.6567 | 0.035* | |
C36 | 1.06093 (17) | 0.13290 (14) | 0.76199 (11) | 0.0186 (6) | |
H36A | 1.0522 | 0.1733 | 0.7827 | 0.022* | |
H36B | 1.026 | 0.0994 | 0.7796 | 0.022* | |
C37 | 1.15354 (18) | 0.11320 (14) | 0.76844 (12) | 0.0206 (6) | |
H37A | 1.1713 | 0.1212 | 0.8067 | 0.025* | |
H37B | 1.1589 | 0.0665 | 0.7613 | 0.025* | |
C38 | 1.21096 (17) | 0.14916 (14) | 0.73033 (12) | 0.0212 (6) | |
C39 | 1.00126 (18) | 0.28058 (14) | 0.72844 (13) | 0.0222 (6) | |
H39A | 1.0125 | 0.2899 | 0.7671 | 0.033* | |
H39B | 0.9889 | 0.3207 | 0.709 | 0.033* | |
H39C | 1.0505 | 0.2601 | 0.712 | 0.033* | |
C40 | 0.82215 (18) | 0.36648 (14) | 0.69287 (11) | 0.0192 (6) | |
H40A | 0.8784 | 0.3627 | 0.6771 | 0.029* | |
H40B | 0.8093 | 0.4119 | 0.6995 | 0.029* | |
H40C | 0.781 | 0.3485 | 0.6673 | 0.029* | |
C41 | 0.66849 (18) | 0.37875 (13) | 0.75955 (13) | 0.0214 (6) | |
H41A | 0.6689 | 0.3909 | 0.7203 | 0.026* | |
H41B | 0.6105 | 0.3662 | 0.7692 | 0.026* | |
C42 | 0.69335 (16) | 0.43663 (14) | 0.79349 (13) | 0.0209 (6) | |
C43 | 0.87346 (16) | 0.36465 (13) | 0.78985 (11) | 0.0166 (5) | |
H43A | 0.9284 | 0.374 | 0.7728 | 0.02* | |
H43B | 0.8466 | 0.4064 | 0.7984 | 0.02* | |
C44 | 0.88901 (19) | 0.32876 (15) | 0.84395 (12) | 0.0227 (6) | |
H44A | 0.839 | 0.3322 | 0.8678 | 0.027* | |
H44B | 0.8994 | 0.2827 | 0.8365 | 0.027* | |
C45 | 0.96465 (18) | 0.35811 (14) | 0.87270 (12) | 0.0224 (6) | |
C46 | 1.0202 (2) | 0.41661 (15) | 0.95112 (13) | 0.0246 (7) | |
H46A | 0.9982 | 0.4508 | 0.9754 | 0.03* | |
H46B | 1.0599 | 0.4367 | 0.9251 | 0.03* | |
C47 | 1.06647 (18) | 0.36664 (15) | 0.98558 (11) | 0.0207 (6) | |
H47 | 1.0858 | 0.3303 | 0.9619 | 0.025* | |
C48 | 1.1401 (2) | 0.39540 (17) | 1.01615 (14) | 0.0308 (8) | |
H48A | 1.1203 | 0.4304 | 1.0397 | 0.046* | |
H48B | 1.1809 | 0.4123 | 0.9898 | 0.046* | |
H48C | 1.1666 | 0.3621 | 1.0387 | 0.046* | |
C49 | 0.91939 (18) | 0.08993 (14) | 0.91683 (11) | 0.0182 (6) | |
H49 | 0.9256 | 0.0526 | 0.9424 | 0.022* | |
C50 | 0.89082 (18) | 0.14950 (13) | 0.94849 (11) | 0.0186 (6) | |
H50 | 0.8536 | 0.1382 | 0.98 | 0.022* | |
C51 | 0.97461 (18) | 0.17573 (13) | 0.96731 (12) | 0.0182 (6) | |
H51 | 0.9952 | 0.1513 | 0.9999 | 0.022* | |
C52 | 1.03166 (19) | 0.16393 (15) | 0.91805 (12) | 0.0223 (6) | |
H52 | 1.0264 | 0.2005 | 0.8917 | 0.027* | |
C53 | 1.1231 (2) | 0.15311 (17) | 0.93144 (13) | 0.0291 (7) | |
H53A | 1.1544 | 0.1461 | 0.8969 | 0.035* | |
H53B | 1.1458 | 0.1922 | 0.9491 | 0.035* | |
C54 | 0.85476 (18) | 0.10701 (13) | 0.82496 (11) | 0.0177 (6) | |
H54 | 0.8943 | 0.1381 | 0.8129 | 0.021* | |
C55 | 0.66598 (18) | 0.01899 (13) | 0.82503 (12) | 0.0203 (6) | |
H55 | 0.6325 | 0.0275 | 0.7936 | 0.024* | |
C56 | 0.63787 (19) | −0.02319 (14) | 0.86545 (13) | 0.0238 (7) | |
C57 | 0.6885 (2) | −0.03592 (14) | 0.91239 (13) | 0.0250 (7) | |
C58 | 0.7662 (2) | −0.00699 (14) | 0.91879 (12) | 0.0237 (6) | |
H58 | 0.8006 | −0.0157 | 0.9497 | 0.028* | |
C59 | 0.79185 (18) | 0.03584 (13) | 0.87740 (12) | 0.0184 (6) | |
C60 | 0.74397 (17) | 0.04863 (12) | 0.83123 (11) | 0.0167 (6) | |
C61 | 0.5540 (2) | −0.05519 (17) | 0.85920 (15) | 0.0350 (8) | |
H61A | 0.5161 | −0.0399 | 0.888 | 0.053* | |
H61B | 0.5607 | −0.1019 | 0.8624 | 0.053* | |
H61C | 0.5305 | −0.0447 | 0.8232 | 0.053* | |
C62 | 0.6572 (3) | −0.08032 (17) | 0.95700 (15) | 0.0393 (9) | |
H62A | 0.6972 | −0.0805 | 0.9875 | 0.059* | |
H62B | 0.6515 | −0.124 | 0.9423 | 0.059* | |
H62C | 0.6025 | −0.0652 | 0.9701 | 0.059* | |
C63 | 0.74226 (18) | 0.16013 (14) | 0.63267 (11) | 0.0200 (6) | |
H63A | 0.7432 | 0.1203 | 0.6105 | 0.024* | |
H63B | 0.6848 | 0.1779 | 0.6301 | 0.024* | |
N1 | 0.65111 (14) | 0.15070 (10) | 0.73191 (9) | 0.0134 (5) | |
N2 | 0.73390 (14) | 0.04848 (10) | 0.69223 (9) | 0.0153 (5) | |
N3 | 0.88029 (13) | 0.12598 (11) | 0.69988 (9) | 0.0152 (5) | |
N4 | 0.77725 (14) | 0.22186 (11) | 0.73194 (9) | 0.0143 (5) | |
N5 | 0.42035 (17) | 0.22324 (14) | 0.62626 (11) | 0.0311 (6) | |
H5A | 0.3695 | 0.2217 | 0.6123 | 0.037* | |
H5B | 0.4622 | 0.2044 | 0.6092 | 0.037* | |
N6 | 0.35252 (18) | 0.10684 (16) | 0.90431 (11) | 0.0371 (7) | |
H6A | 0.3337 | 0.0843 | 0.9322 | 0.044* | |
H6B | 0.3737 | 0.1454 | 0.9098 | 0.044* | |
N7 | 0.53576 (17) | −0.02341 (14) | 0.54999 (11) | 0.0289 (6) | |
H7A | 0.4997 | −0.0007 | 0.5308 | 0.035* | |
H7B | 0.5226 | −0.0625 | 0.5609 | 0.035* | |
N8 | 0.77766 (17) | −0.15596 (12) | 0.84060 (11) | 0.0269 (6) | |
H8A | 0.7801 | −0.1731 | 0.8735 | 0.032* | |
H8B | 0.733 | −0.1619 | 0.8201 | 0.032* | |
N9 | 1.22518 (16) | 0.21052 (12) | 0.74193 (11) | 0.0251 (6) | |
H9A | 1.2579 | 0.2336 | 0.7206 | 0.03* | |
H9B | 1.2019 | 0.2281 | 0.771 | 0.03* | |
N10 | 0.70352 (15) | 0.49194 (11) | 0.76769 (11) | 0.0220 (5) | |
H10A | 0.7176 | 0.5266 | 0.7862 | 0.026* | |
H10B | 0.6962 | 0.4941 | 0.732 | 0.026* | |
N11 | 0.95123 (16) | 0.38823 (12) | 0.92076 (10) | 0.0236 (6) | |
H11 | 0.9 | 0.3907 | 0.9339 | 0.028* | |
N12 | 0.86414 (15) | 0.07301 (11) | 0.87206 (9) | 0.0183 (5) | |
N13 | 0.78637 (14) | 0.09329 (11) | 0.79744 (10) | 0.0168 (5) | |
O1 | 0.37668 (13) | 0.28110 (11) | 0.69856 (9) | 0.0291 (5) | |
O2 | 0.31973 (16) | 0.02849 (11) | 0.84433 (10) | 0.0373 (6) | |
O3 | 0.63201 (15) | 0.05629 (11) | 0.54817 (9) | 0.0324 (5) | |
O4 | 0.90527 (13) | −0.11217 (11) | 0.85040 (9) | 0.0284 (5) | |
O5 | 1.24248 (13) | 0.12188 (9) | 0.68965 (8) | 0.0255 (5) | |
O6 | 0.70306 (14) | 0.43141 (10) | 0.84391 (9) | 0.0276 (5) | |
O7 | 1.03526 (13) | 0.35586 (11) | 0.85197 (9) | 0.0277 (5) | |
O8 | 1.07770 (13) | 0.24025 (10) | 1.05514 (8) | 0.0236 (5) | |
O9 | 0.92504 (13) | 0.26532 (10) | 1.07792 (8) | 0.0254 (5) | |
O10 | 0.97022 (13) | 0.24291 (9) | 0.97934 (8) | 0.0219 (4) | |
O11 | 1.00484 (13) | 0.34389 (10) | 1.02491 (8) | 0.0213 (4) | |
O12 | 0.99877 (13) | 0.10570 (10) | 0.89316 (8) | 0.0233 (5) | |
O13 | 0.85129 (13) | 0.19134 (10) | 0.91126 (8) | 0.0211 (4) | |
H13A | 0.8165 | 0.2144 | 0.9281 | 0.032* | |
O14 | 1.13589 (14) | 0.10023 (11) | 0.96627 (9) | 0.0310 (5) | |
H14 | 1.1365 | 0.0662 | 0.9477 | 0.047* | |
P | 0.99602 (5) | 0.26981 (4) | 1.03867 (3) | 0.01786 (15) | |
Co | 0.76241 (2) | 0.134650 (17) | 0.712480 (15) | 0.01377 (8) | |
O1W | 0.24256 (14) | 0.23269 (12) | 0.03362 (9) | 0.0364 (5) | |
H1Y | 0.1905 | 0.2353 | 0.0404 | 0.055* | |
H1Z | 0.2506 | 0.1926 | 0.038 | 0.055* | |
O2W | 0.16924 (15) | 0.26920 (11) | 0.84058 (9) | 0.0344 (5) | |
H2Y | 0.1288 | 0.2955 | 0.844 | 0.052* | |
H2Z | 0.2014 | 0.277 | 0.8675 | 0.052* | |
O3W | 0.77424 (14) | 0.20544 (11) | 0.07112 (9) | 0.0323 (5) | |
H3Y | 0.8215 | 0.2242 | 0.0733 | 0.048* | |
H3Z | 0.765 | 0.2236 | 0.0405 | 0.048* | |
O4W | 0.02890 (15) | 0.97971 (11) | 0.83342 (10) | 0.0361 (6) | |
H4Y | −0.009 | 0.9517 | 0.8386 | 0.054* | |
H4Z | 0.0203 | 1.015 | 0.8502 | 0.054* | |
O5W | 0.56885 (15) | 0.37872 (12) | 0.90100 (11) | 0.0425 (7) | |
H5Y | 0.61 | 0.395 | 0.8838 | 0.064* | |
H5Z | 0.5719 | 0.341 | 0.9142 | 0.064* | |
O6W | 0.16377 (18) | 0.99142 (14) | 0.90416 (11) | 0.0514 (7) | |
H6Y | 0.1221 | 0.9876 | 0.8827 | 0.077* | |
H6Z | 0.2083 | 1.0019 | 0.8873 | 0.077* | |
O7W | 0.39819 (17) | 0.06258 (15) | 0.50689 (13) | 0.0541 (7) | |
H7Y | 0.3803 | 0.047 | 0.4769 | 0.081* | |
H7Z | 0.3599 | 0.0546 | 0.5302 | 0.081* | |
O8W | 0.52174 (18) | 0.15943 (14) | 0.53674 (13) | 0.0531 (7) | |
H8Y | 0.5556 | 0.1281 | 0.5402 | 0.08* | |
H8Z | 0.4856 | 0.1312 | 0.5279 | 0.08* | |
O9W | 0.23533 (19) | 0.20076 (17) | 0.59497 (11) | 0.0653 (9) | |
H9Y | 0.1943 | 0.2254 | 0.5878 | 0.098* | |
H9Z | 0.2377 | 0.1771 | 0.6233 | 0.098* | |
O10W | 0.7312 (2) | 0.53583 (19) | 0.91553 (14) | 0.0788 (10) | |
H10Y | 0.7225 | 0.5046 | 0.8938 | 0.118* | |
H10Z | 0.7647 | 0.5292 | 0.942 | 0.118* | |
O11W | 0.9076 (3) | 0.78596 (18) | 0.92935 (15) | 0.0816 (11) | |
O12A | 0.2820 (3) | 0.0854 (2) | 0.0213 (2) | 0.0374 (11) | 0.6 |
O12B | 0.2685 (5) | 0.1070 (4) | 0.0465 (3) | 0.0409 (17) | 0.4 |
H12W | 0.2297 | 0.1049 | 0.0227 | 0.061* | 0.4 |
H12X | 0.2501 | 0.0959 | 0.0778 | 0.061* | 0.4 |
C64A | 0.7987 (5) | 0.2060 (8) | 0.6069 (3) | 0.034 (2) | 0.615 (4) |
H64A | 0.8544 | 0.1854 | 0.6033 | 0.041* | 0.615 (4) |
H64B | 0.8052 | 0.2432 | 0.6318 | 0.041* | 0.615 (4) |
C65A | 0.7728 (4) | 0.2315 (3) | 0.5502 (2) | 0.0380 (16) | 0.615 (4) |
H65A | 0.7537 | 0.1949 | 0.5267 | 0.046* | 0.615 (4) |
C66A | 0.7015 (4) | 0.2816 (4) | 0.5555 (3) | 0.060 (2) | 0.615 (4) |
H66A | 0.654 | 0.2624 | 0.575 | 0.072* | 0.615 (4) |
H66B | 0.6835 | 0.2953 | 0.5189 | 0.072* | 0.615 (4) |
H66C | 0.7219 | 0.319 | 0.576 | 0.072* | 0.615 (4) |
C67A | 0.8515 (5) | 0.2633 (4) | 0.5243 (4) | 0.0610 (18) | 0.615 (4) |
H67A | 0.8407 | 0.2726 | 0.4856 | 0.073* | 0.615 (4) |
H67B | 0.8993 | 0.234 | 0.5274 | 0.073* | 0.615 (4) |
H67C | 0.8641 | 0.3035 | 0.5437 | 0.073* | 0.615 (4) |
C64B | 0.7931 (9) | 0.2160 (13) | 0.6118 (4) | 0.034 (2) | 0.385 (4) |
H64C | 0.8462 | 0.218 | 0.6326 | 0.041* | 0.385 (4) |
H64D | 0.7619 | 0.2563 | 0.6192 | 0.041* | 0.385 (4) |
C65B | 0.8137 (6) | 0.2132 (5) | 0.5503 (4) | 0.0371 (16) | 0.385 (4) |
H65B | 0.8546 | 0.1777 | 0.5431 | 0.045* | 0.385 (4) |
C66B | 0.7332 (5) | 0.2021 (4) | 0.5160 (3) | 0.029 (2) | 0.385 (4) |
H66D | 0.6933 | 0.237 | 0.5232 | 0.043* | 0.385 (4) |
H66E | 0.7079 | 0.1609 | 0.5263 | 0.043* | 0.385 (4) |
H66F | 0.7475 | 0.2016 | 0.477 | 0.043* | 0.385 (4) |
C67B | 0.8537 (7) | 0.2788 (6) | 0.5346 (6) | 0.0609 (18) | 0.385 (4) |
H67D | 0.8171 | 0.3139 | 0.5466 | 0.073* | 0.385 (4) |
H67E | 0.8609 | 0.281 | 0.4947 | 0.073* | 0.385 (4) |
H67F | 0.9085 | 0.2829 | 0.5524 | 0.073* | 0.385 (4) |
O15 | 0.6320 (5) | 0.3506 (5) | 0.6113 (3) | 0.066 (3) | 0.385 (4) |
C70 | 0.5537 (7) | 0.3265 (5) | 0.5318 (4) | 0.044 (3) | 0.385 (4) |
H70A | 0.5298 | 0.2925 | 0.5548 | 0.067* | 0.385 (4) |
H70B | 0.5818 | 0.3071 | 0.5001 | 0.067* | 0.385 (4) |
H70C | 0.5088 | 0.3549 | 0.5191 | 0.067* | 0.385 (4) |
C69 | 0.6160 (6) | 0.3646 (6) | 0.5646 (4) | 0.051 (3) | 0.385 (4) |
C68 | 0.6580 (14) | 0.4192 (11) | 0.5326 (8) | 0.150 (11) | 0.385 (4) |
H68A | 0.6978 | 0.4416 | 0.5565 | 0.224* | 0.385 (4) |
H68B | 0.6152 | 0.4495 | 0.5199 | 0.224* | 0.385 (4) |
H68C | 0.6879 | 0.4013 | 0.501 | 0.224* | 0.385 (4) |
O13W | 0.6540 (8) | 0.4881 (5) | 0.5058 (6) | 0.102 (4) | 0.35 |
O14W | 0.7010 (16) | 0.4291 (12) | 0.5930 (11) | 0.177 (9)* | 0.3 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0142 (14) | 0.0120 (13) | 0.0183 (13) | 0.0016 (10) | −0.0008 (11) | −0.0009 (11) |
C2 | 0.0124 (13) | 0.0164 (14) | 0.0177 (14) | −0.0010 (11) | 0.0007 (11) | −0.0009 (11) |
C3 | 0.0136 (13) | 0.0178 (14) | 0.0182 (14) | 0.0009 (11) | 0.0003 (11) | −0.0028 (11) |
C4 | 0.0128 (13) | 0.0174 (14) | 0.0139 (13) | 0.0011 (10) | −0.0012 (10) | 0.0039 (10) |
C5 | 0.0155 (14) | 0.0168 (14) | 0.0164 (13) | −0.0039 (11) | −0.0007 (10) | −0.0018 (11) |
C6 | 0.0168 (14) | 0.0142 (13) | 0.0149 (13) | −0.0047 (11) | −0.0004 (11) | −0.0013 (11) |
C7 | 0.0182 (15) | 0.0155 (14) | 0.0185 (14) | −0.0018 (11) | −0.0002 (11) | −0.0032 (11) |
C8 | 0.0152 (14) | 0.0136 (13) | 0.0241 (14) | 0.0003 (11) | 0.0019 (11) | −0.0056 (10) |
C9 | 0.0186 (14) | 0.0142 (14) | 0.0156 (14) | 0.0005 (11) | −0.0003 (11) | −0.0037 (11) |
C10 | 0.0170 (14) | 0.0179 (14) | 0.0215 (15) | 0.0003 (11) | 0.0008 (11) | −0.0049 (12) |
C11 | 0.0147 (14) | 0.0165 (14) | 0.0152 (13) | 0.0019 (11) | −0.0001 (11) | 0.0006 (11) |
C12 | 0.0132 (14) | 0.0174 (14) | 0.0216 (14) | 0.0006 (11) | 0.0011 (11) | −0.0014 (11) |
C13 | 0.0118 (12) | 0.0152 (13) | 0.0238 (15) | −0.0013 (10) | 0.0014 (10) | 0.0002 (11) |
C14 | 0.0156 (13) | 0.0202 (14) | 0.0146 (13) | −0.0012 (11) | 0.0040 (11) | 0.0022 (11) |
C15 | 0.0167 (13) | 0.0153 (13) | 0.0171 (14) | −0.0026 (11) | 0.0005 (10) | 0.0003 (11) |
C16 | 0.0187 (14) | 0.0128 (13) | 0.0106 (12) | −0.0010 (11) | −0.0018 (10) | 0.0010 (10) |
C17 | 0.0124 (13) | 0.0160 (14) | 0.0187 (14) | −0.0007 (11) | −0.0001 (11) | 0.0020 (11) |
C18 | 0.0132 (14) | 0.0139 (13) | 0.0202 (14) | −0.0018 (11) | −0.0004 (11) | 0.0011 (10) |
C19 | 0.0112 (13) | 0.0145 (13) | 0.0187 (13) | 0.0025 (10) | −0.0008 (10) | 0.0000 (11) |
C20 | 0.0154 (14) | 0.0136 (13) | 0.0170 (14) | −0.0004 (11) | 0.0005 (11) | −0.0006 (11) |
C21 | 0.0156 (13) | 0.0153 (13) | 0.0252 (15) | 0.0004 (11) | 0.0022 (11) | −0.0007 (12) |
C22 | 0.0124 (13) | 0.0217 (15) | 0.0235 (15) | 0.0014 (11) | −0.0005 (11) | 0.0026 (12) |
C23 | 0.0140 (14) | 0.0247 (16) | 0.0284 (16) | 0.0005 (12) | 0.0010 (12) | 0.0102 (13) |
C24 | 0.0133 (13) | 0.0184 (14) | 0.0218 (15) | −0.0007 (10) | 0.0002 (11) | −0.0011 (11) |
C25 | 0.0167 (14) | 0.0223 (15) | 0.0241 (15) | 0.0004 (12) | 0.0018 (11) | 0.0013 (12) |
C26 | 0.0165 (15) | 0.0329 (18) | 0.0260 (16) | −0.0076 (13) | 0.0005 (12) | −0.0014 (13) |
C27 | 0.0155 (14) | 0.0287 (17) | 0.0331 (18) | −0.0016 (13) | −0.0001 (13) | −0.0110 (14) |
C28 | 0.0218 (15) | 0.0201 (15) | 0.0250 (15) | −0.0050 (12) | −0.0015 (12) | −0.0028 (12) |
C29 | 0.0209 (15) | 0.0204 (15) | 0.0189 (14) | −0.0008 (12) | 0.0006 (11) | −0.0067 (12) |
C30 | 0.0262 (16) | 0.0235 (16) | 0.0162 (14) | 0.0010 (13) | −0.0001 (12) | −0.0049 (12) |
C31 | 0.0199 (16) | 0.0171 (13) | 0.0243 (15) | −0.0010 (12) | 0.0010 (12) | −0.0022 (11) |
C32 | 0.0175 (15) | 0.0235 (15) | 0.0260 (15) | 0.0009 (12) | −0.0012 (12) | −0.0014 (12) |
C33 | 0.0220 (16) | 0.0202 (15) | 0.0266 (16) | 0.0050 (12) | −0.0009 (12) | −0.0090 (12) |
C34 | 0.0237 (17) | 0.0283 (17) | 0.0225 (16) | −0.0012 (13) | 0.0059 (12) | −0.0039 (13) |
C35 | 0.0165 (14) | 0.0186 (15) | 0.0359 (18) | 0.0013 (12) | 0.0007 (13) | −0.0067 (13) |
C36 | 0.0171 (14) | 0.0194 (14) | 0.0195 (14) | −0.0021 (12) | 0.0013 (11) | 0.0013 (12) |
C37 | 0.0177 (15) | 0.0222 (15) | 0.0219 (14) | 0.0018 (12) | −0.0047 (11) | 0.0019 (12) |
C38 | 0.0120 (13) | 0.0213 (15) | 0.0302 (16) | 0.0021 (11) | −0.0038 (11) | 0.0010 (12) |
C39 | 0.0139 (14) | 0.0210 (15) | 0.0317 (17) | −0.0006 (12) | 0.0019 (12) | −0.0008 (12) |
C40 | 0.0193 (13) | 0.0179 (14) | 0.0205 (14) | −0.0034 (12) | −0.0005 (11) | 0.0044 (12) |
C41 | 0.0156 (14) | 0.0181 (15) | 0.0304 (16) | −0.0002 (11) | 0.0011 (12) | 0.0014 (12) |
C42 | 0.0118 (14) | 0.0201 (15) | 0.0307 (17) | 0.0022 (11) | 0.0052 (12) | −0.0002 (13) |
C43 | 0.0146 (12) | 0.0145 (12) | 0.0206 (13) | −0.0015 (11) | −0.0012 (11) | −0.0002 (12) |
C44 | 0.0268 (16) | 0.0219 (16) | 0.0193 (15) | −0.0055 (13) | −0.0030 (12) | 0.0025 (12) |
C45 | 0.0220 (15) | 0.0195 (15) | 0.0258 (16) | −0.0022 (12) | −0.0041 (12) | 0.0070 (13) |
C46 | 0.0299 (17) | 0.0195 (15) | 0.0244 (16) | −0.0051 (13) | −0.0086 (13) | 0.0000 (12) |
C47 | 0.0206 (14) | 0.0213 (15) | 0.0203 (14) | −0.0051 (13) | −0.0023 (11) | 0.0009 (12) |
C48 | 0.0278 (18) | 0.0345 (19) | 0.0301 (18) | −0.0091 (14) | −0.0082 (14) | 0.0022 (15) |
C49 | 0.0174 (14) | 0.0186 (14) | 0.0186 (14) | −0.0012 (11) | −0.0036 (11) | −0.0008 (11) |
C50 | 0.0206 (14) | 0.0182 (15) | 0.0170 (14) | 0.0010 (11) | 0.0006 (11) | 0.0004 (11) |
C51 | 0.0232 (15) | 0.0150 (14) | 0.0162 (14) | 0.0000 (11) | −0.0024 (11) | −0.0005 (11) |
C52 | 0.0225 (15) | 0.0257 (16) | 0.0187 (15) | −0.0026 (13) | −0.0003 (12) | −0.0045 (12) |
C53 | 0.0223 (16) | 0.039 (2) | 0.0257 (17) | −0.0032 (14) | −0.0010 (13) | −0.0070 (14) |
C54 | 0.0175 (14) | 0.0149 (13) | 0.0206 (14) | 0.0012 (11) | 0.0002 (11) | −0.0026 (11) |
C55 | 0.0192 (15) | 0.0159 (14) | 0.0258 (15) | 0.0015 (12) | −0.0001 (12) | −0.0042 (12) |
C56 | 0.0238 (16) | 0.0171 (15) | 0.0306 (17) | −0.0011 (12) | 0.0047 (13) | −0.0018 (13) |
C57 | 0.0315 (18) | 0.0165 (15) | 0.0270 (16) | −0.0021 (13) | 0.0045 (14) | −0.0026 (12) |
C58 | 0.0292 (16) | 0.0218 (15) | 0.0202 (14) | 0.0034 (13) | −0.0007 (13) | −0.0009 (11) |
C59 | 0.0193 (14) | 0.0148 (14) | 0.0210 (15) | 0.0016 (11) | 0.0004 (11) | −0.0063 (11) |
C60 | 0.0191 (15) | 0.0128 (12) | 0.0183 (13) | 0.0037 (11) | 0.0030 (11) | −0.0033 (10) |
C61 | 0.0292 (18) | 0.0330 (19) | 0.043 (2) | −0.0080 (15) | 0.0029 (15) | 0.0029 (16) |
C62 | 0.049 (2) | 0.034 (2) | 0.0348 (19) | −0.0156 (17) | 0.0043 (17) | 0.0065 (16) |
C63 | 0.0218 (15) | 0.0239 (14) | 0.0144 (13) | −0.0075 (12) | 0.0015 (12) | −0.0016 (11) |
N1 | 0.0139 (11) | 0.0127 (11) | 0.0137 (11) | 0.0012 (9) | 0.0027 (9) | −0.0021 (9) |
N2 | 0.0149 (11) | 0.0138 (11) | 0.0173 (11) | −0.0029 (10) | 0.0013 (9) | −0.0029 (9) |
N3 | 0.0114 (11) | 0.0155 (12) | 0.0187 (12) | −0.0018 (9) | 0.0014 (8) | −0.0006 (9) |
N4 | 0.0134 (12) | 0.0164 (11) | 0.0130 (10) | 0.0011 (9) | 0.0002 (8) | −0.0002 (9) |
N5 | 0.0180 (13) | 0.0449 (18) | 0.0306 (15) | 0.0007 (12) | −0.0074 (11) | −0.0008 (13) |
N6 | 0.0362 (17) | 0.0500 (19) | 0.0250 (15) | −0.0201 (14) | 0.0053 (12) | −0.0057 (13) |
N7 | 0.0272 (14) | 0.0337 (15) | 0.0259 (14) | 0.0009 (12) | −0.0063 (11) | −0.0019 (12) |
N8 | 0.0286 (15) | 0.0269 (14) | 0.0251 (13) | −0.0012 (11) | −0.0049 (11) | 0.0025 (11) |
N9 | 0.0205 (13) | 0.0201 (12) | 0.0348 (15) | −0.0015 (10) | 0.0019 (11) | 0.0000 (11) |
N10 | 0.0240 (13) | 0.0151 (12) | 0.0268 (13) | 0.0003 (10) | 0.0006 (10) | −0.0021 (10) |
N11 | 0.0246 (14) | 0.0265 (14) | 0.0198 (13) | −0.0019 (11) | −0.0042 (10) | 0.0029 (11) |
N12 | 0.0207 (13) | 0.0170 (12) | 0.0172 (12) | −0.0017 (10) | −0.0036 (10) | −0.0026 (10) |
N13 | 0.0149 (11) | 0.0151 (11) | 0.0205 (12) | −0.0003 (9) | −0.0019 (9) | −0.0015 (9) |
O1 | 0.0165 (11) | 0.0345 (13) | 0.0363 (13) | 0.0052 (9) | −0.0013 (9) | 0.0051 (10) |
O2 | 0.0498 (15) | 0.0315 (13) | 0.0306 (13) | −0.0160 (12) | −0.0073 (11) | 0.0032 (10) |
O3 | 0.0330 (13) | 0.0299 (13) | 0.0344 (13) | −0.0002 (10) | −0.0034 (10) | 0.0044 (10) |
O4 | 0.0225 (12) | 0.0338 (13) | 0.0289 (12) | 0.0011 (9) | −0.0049 (9) | −0.0049 (10) |
O5 | 0.0234 (11) | 0.0228 (11) | 0.0303 (11) | 0.0003 (9) | 0.0050 (9) | 0.0013 (9) |
O6 | 0.0313 (12) | 0.0245 (11) | 0.0269 (12) | 0.0017 (9) | 0.0069 (9) | 0.0012 (9) |
O7 | 0.0244 (11) | 0.0305 (12) | 0.0284 (11) | −0.0021 (10) | −0.0043 (9) | −0.0018 (10) |
O8 | 0.0241 (11) | 0.0216 (11) | 0.0252 (11) | −0.0002 (9) | −0.0035 (9) | 0.0006 (9) |
O9 | 0.0253 (11) | 0.0300 (12) | 0.0208 (10) | −0.0029 (9) | 0.0029 (9) | −0.0013 (9) |
O10 | 0.0295 (12) | 0.0164 (10) | 0.0197 (10) | 0.0006 (9) | −0.0058 (8) | −0.0021 (8) |
O11 | 0.0239 (11) | 0.0211 (11) | 0.0189 (10) | −0.0020 (9) | 0.0000 (8) | −0.0028 (8) |
O12 | 0.0185 (11) | 0.0293 (11) | 0.0222 (11) | −0.0017 (9) | −0.0001 (8) | −0.0100 (9) |
O13 | 0.0215 (11) | 0.0210 (11) | 0.0209 (10) | 0.0063 (9) | −0.0022 (8) | −0.0038 (8) |
O14 | 0.0280 (12) | 0.0352 (13) | 0.0298 (12) | 0.0086 (10) | −0.0059 (10) | −0.0085 (10) |
P | 0.0196 (4) | 0.0181 (4) | 0.0158 (3) | −0.0013 (3) | −0.0017 (3) | −0.0020 (3) |
Co | 0.01113 (16) | 0.01275 (16) | 0.01742 (17) | −0.00076 (14) | 0.00072 (14) | −0.00235 (14) |
O1W | 0.0202 (12) | 0.0531 (15) | 0.0358 (12) | −0.0117 (11) | −0.0001 (10) | −0.0047 (11) |
O2W | 0.0327 (13) | 0.0348 (13) | 0.0356 (13) | 0.0054 (11) | −0.0046 (10) | −0.0068 (11) |
O3W | 0.0263 (12) | 0.0349 (13) | 0.0358 (13) | −0.0041 (10) | 0.0022 (10) | −0.0003 (10) |
O4W | 0.0342 (13) | 0.0290 (13) | 0.0451 (15) | 0.0030 (10) | 0.0039 (11) | −0.0073 (11) |
O5W | 0.0273 (13) | 0.0349 (14) | 0.0654 (17) | 0.0090 (11) | 0.0143 (12) | 0.0230 (13) |
O6W | 0.0495 (17) | 0.0555 (18) | 0.0492 (16) | −0.0003 (14) | −0.0062 (14) | −0.0182 (14) |
O7W | 0.0375 (15) | 0.0628 (19) | 0.0620 (19) | 0.0057 (14) | −0.0038 (14) | 0.0118 (15) |
O8W | 0.0428 (16) | 0.0432 (16) | 0.073 (2) | 0.0146 (13) | 0.0018 (14) | 0.0012 (15) |
O9W | 0.0463 (17) | 0.115 (3) | 0.0347 (15) | −0.0134 (19) | −0.0037 (14) | 0.0125 (16) |
O10W | 0.073 (2) | 0.099 (3) | 0.064 (2) | −0.006 (2) | 0.0026 (19) | 0.0061 (19) |
O11W | 0.096 (3) | 0.075 (2) | 0.074 (2) | −0.018 (2) | −0.034 (2) | 0.0183 (19) |
O12A | 0.031 (3) | 0.050 (3) | 0.031 (3) | −0.003 (2) | −0.008 (2) | −0.002 (2) |
O12B | 0.040 (4) | 0.043 (4) | 0.040 (4) | −0.012 (3) | 0.005 (4) | −0.004 (3) |
C64A | 0.036 (2) | 0.037 (5) | 0.028 (2) | −0.014 (2) | −0.0057 (18) | 0.008 (3) |
C65A | 0.037 (4) | 0.052 (4) | 0.025 (2) | −0.021 (3) | 0.000 (3) | 0.005 (2) |
C66A | 0.061 (2) | 0.060 (2) | 0.059 (2) | 0.0009 (10) | −0.0007 (10) | 0.0005 (10) |
C67A | 0.0619 (19) | 0.061 (2) | 0.0599 (19) | −0.0024 (8) | 0.0007 (8) | 0.0015 (8) |
C64B | 0.036 (2) | 0.037 (5) | 0.028 (2) | −0.014 (2) | −0.0055 (18) | 0.008 (3) |
C65B | 0.036 (4) | 0.051 (4) | 0.024 (2) | −0.021 (3) | 0.000 (3) | 0.004 (3) |
C66B | 0.039 (5) | 0.036 (5) | 0.011 (4) | 0.002 (4) | −0.003 (3) | 0.002 (3) |
C67B | 0.0618 (19) | 0.061 (2) | 0.060 (2) | −0.0020 (8) | 0.0007 (8) | 0.0010 (8) |
O15 | 0.054 (5) | 0.086 (7) | 0.058 (5) | 0.005 (5) | −0.011 (4) | 0.007 (5) |
C70 | 0.048 (6) | 0.038 (6) | 0.048 (6) | −0.007 (5) | 0.008 (5) | −0.002 (5) |
C69 | 0.047 (6) | 0.072 (8) | 0.035 (6) | 0.004 (6) | 0.013 (5) | 0.020 (6) |
C68 | 0.16 (2) | 0.18 (2) | 0.106 (14) | −0.127 (18) | −0.076 (14) | 0.070 (14) |
O13W | 0.076 (8) | 0.065 (7) | 0.165 (13) | 0.001 (6) | −0.010 (8) | −0.001 (8) |
C1—N1 | 1.504 (3) | C48—H48A | 0.98 |
C1—C20 | 1.535 (4) | C48—H48B | 0.98 |
C1—C19 | 1.558 (4) | C48—H48C | 0.98 |
C1—C2 | 1.582 (4) | C49—O12 | 1.430 (4) |
C2—C21 | 1.528 (4) | C49—N12 | 1.447 (3) |
C2—C22 | 1.560 (4) | C49—C50 | 1.529 (4) |
C2—C3 | 1.561 (4) | C49—H49 | 1 |
C3—C4 | 1.523 (4) | C50—O13 | 1.407 (3) |
C3—C24 | 1.559 (4) | C50—C51 | 1.515 (4) |
C3—H3 | 1 | C50—H50 | 1 |
C4—N1 | 1.291 (3) | C51—O10 | 1.429 (3) |
C4—C5 | 1.453 (4) | C51—C52 | 1.528 (4) |
C5—C6 | 1.359 (4) | C51—H51 | 1 |
C5—C27 | 1.525 (4) | C52—O12 | 1.453 (4) |
C6—N2 | 1.405 (4) | C52—C53 | 1.512 (4) |
C6—C7 | 1.552 (4) | C52—H52 | 1 |
C7—C28 | 1.534 (4) | C53—O14 | 1.405 (4) |
C7—C8 | 1.559 (4) | C53—H53A | 0.99 |
C7—C29 | 1.564 (4) | C53—H53B | 0.99 |
C8—C9 | 1.501 (4) | C54—N13 | 1.313 (4) |
C8—C31 | 1.562 (4) | C54—N12 | 1.358 (4) |
C8—H8 | 1 | C54—H54 | 0.95 |
C9—N2 | 1.338 (3) | C55—C56 | 1.394 (4) |
C9—C10 | 1.383 (4) | C55—C60 | 1.397 (4) |
C10—C11 | 1.383 (4) | C55—H55 | 0.95 |
C10—H10 | 0.95 | C56—C57 | 1.426 (5) |
C11—N3 | 1.346 (3) | C56—C61 | 1.503 (4) |
C11—C12 | 1.522 (4) | C57—C58 | 1.388 (5) |
C12—C35 | 1.531 (4) | C57—C62 | 1.512 (4) |
C12—C34 | 1.534 (4) | C58—C59 | 1.407 (4) |
C12—C13 | 1.554 (4) | C58—H58 | 0.95 |
C13—C14 | 1.534 (4) | C59—C60 | 1.387 (4) |
C13—C36 | 1.549 (4) | C59—N12 | 1.395 (4) |
C13—H13 | 1 | C60—N13 | 1.414 (4) |
C14—C15 | 1.371 (4) | C61—H61A | 0.98 |
C14—N3 | 1.386 (3) | C61—H61B | 0.98 |
C15—C16 | 1.446 (4) | C61—H61C | 0.98 |
C15—C39 | 1.518 (4) | C62—H62A | 0.98 |
C16—N4 | 1.303 (4) | C62—H62B | 0.98 |
C16—C17 | 1.543 (4) | C62—H62C | 0.98 |
C17—C43 | 1.542 (4) | C63—C64A | 1.454 (10) |
C17—C40 | 1.544 (4) | C63—C64B | 1.506 (18) |
C17—C18 | 1.560 (4) | C63—Co | 2.044 (3) |
C18—C19 | 1.536 (4) | C63—H63A | 0.99 |
C18—C41 | 1.543 (4) | C63—H63B | 0.99 |
C18—H18 | 1 | N1—Co | 1.869 (2) |
C19—N4 | 1.490 (3) | N2—Co | 1.914 (2) |
C19—H19 | 1 | N3—Co | 1.915 (2) |
C20—H20A | 0.98 | N4—Co | 1.889 (2) |
C20—H20B | 0.98 | N5—H5A | 0.88 |
C20—H20C | 0.98 | N5—H5B | 0.88 |
C21—H21A | 0.98 | N6—H6A | 0.88 |
C21—H21B | 0.98 | N6—H6B | 0.88 |
C21—H21C | 0.98 | N7—H7A | 0.88 |
C22—C23 | 1.526 (4) | N7—H7B | 0.88 |
C22—H22A | 0.99 | N8—H8A | 0.88 |
C22—H22B | 0.99 | N8—H8B | 0.88 |
C23—O1 | 1.235 (4) | N9—H9A | 0.88 |
C23—N5 | 1.334 (4) | N9—H9B | 0.88 |
C24—C25 | 1.537 (4) | N10—H10A | 0.88 |
C24—H24A | 0.99 | N10—H10B | 0.88 |
C24—H24B | 0.99 | N11—H11 | 0.88 |
C25—C26 | 1.513 (4) | N13—Co | 2.277 (2) |
C25—H25A | 0.99 | O8—P | 1.496 (2) |
C25—H25B | 0.99 | O9—P | 1.486 (2) |
C26—O2 | 1.248 (4) | O10—P | 1.606 (2) |
C26—N6 | 1.320 (4) | O11—P | 1.583 (2) |
C27—H27A | 0.98 | O13—H13A | 0.84 |
C27—H27B | 0.98 | O14—H14 | 0.84 |
C27—H27C | 0.98 | O1W—H1Y | 0.8492 |
C28—H28A | 0.98 | O1W—H1Z | 0.8508 |
C28—H28B | 0.98 | O2W—H2Y | 0.8503 |
C28—H28C | 0.98 | O2W—H2Z | 0.8498 |
C29—C30 | 1.520 (4) | O3W—H3Y | 0.8504 |
C29—H29A | 0.99 | O3W—H3Z | 0.8507 |
C29—H29B | 0.99 | O4W—H4Y | 0.8489 |
C30—O3 | 1.240 (4) | O4W—H4Z | 0.8503 |
C30—N7 | 1.339 (4) | O5W—H5Y | 0.8505 |
C31—C32 | 1.532 (4) | O5W—H5Z | 0.849 |
C31—H31A | 0.99 | O6W—H6Y | 0.851 |
C31—H31B | 0.99 | O6W—H6Z | 0.8501 |
C32—C33 | 1.498 (4) | O7W—H7Y | 0.8491 |
C32—H32A | 0.99 | O7W—H7Z | 0.8509 |
C32—H32B | 0.99 | O8W—H8Y | 0.8499 |
C33—O4 | 1.247 (4) | O8W—H8Z | 0.8506 |
C33—N8 | 1.333 (4) | O9W—H9Y | 0.8495 |
C34—H34A | 0.98 | O9W—H9Z | 0.8506 |
C34—H34B | 0.98 | O10W—H10Y | 0.85 |
C34—H34C | 0.98 | O10W—H10Z | 0.8505 |
C35—H35A | 0.98 | O12A—H12W | 0.9298 |
C35—H35B | 0.98 | O12B—H12W | 0.8509 |
C35—H35C | 0.98 | O12B—H12X | 0.8504 |
C36—C37 | 1.542 (4) | C64A—C65A | 1.538 (7) |
C36—H36A | 0.99 | C64A—H64A | 0.99 |
C36—H36B | 0.99 | C64A—H64B | 0.99 |
C37—C38 | 1.505 (4) | C65A—C66A | 1.549 (9) |
C37—H37A | 0.99 | C65A—C67A | 1.555 (7) |
C37—H37B | 0.99 | C65A—H65A | 1 |
C38—O5 | 1.249 (4) | C66A—H66A | 0.98 |
C38—N9 | 1.327 (4) | C66A—H66B | 0.98 |
C39—H39A | 0.98 | C66A—H66C | 0.98 |
C39—H39B | 0.98 | C67A—H67A | 0.98 |
C39—H39C | 0.98 | C67A—H67B | 0.98 |
C40—H40A | 0.98 | C67A—H67C | 0.98 |
C40—H40B | 0.98 | C64B—C65B | 1.538 (7) |
C40—H40C | 0.98 | C64B—H64C | 0.99 |
C41—C42 | 1.514 (4) | C64B—H64D | 0.99 |
C41—H41A | 0.99 | C65B—C66B | 1.549 (9) |
C41—H41B | 0.99 | C65B—C67B | 1.555 (7) |
C42—O6 | 1.245 (4) | C65B—H65B | 1 |
C42—N10 | 1.321 (4) | C66B—H66D | 0.98 |
C43—C44 | 1.537 (4) | C66B—H66E | 0.98 |
C43—H43A | 0.99 | C66B—H66F | 0.98 |
C43—H43B | 0.99 | C67B—H67D | 0.98 |
C44—C45 | 1.524 (4) | C67B—H67E | 0.98 |
C44—H44A | 0.99 | C67B—H67F | 0.98 |
C44—H44B | 0.99 | O15—C69 | 1.205 (10) |
C45—O7 | 1.236 (4) | C70—C69 | 1.503 (12) |
C45—N11 | 1.347 (4) | C70—H70A | 0.98 |
C46—N11 | 1.452 (4) | C70—H70B | 0.98 |
C46—C47 | 1.527 (4) | C70—H70C | 0.98 |
C46—H46A | 0.99 | C69—C68 | 1.531 (14) |
C46—H46B | 0.99 | C68—H68A | 0.98 |
C47—O11 | 1.453 (3) | C68—H68B | 0.98 |
C47—C48 | 1.515 (4) | C68—H68C | 0.98 |
C47—H47 | 1 | ||
N1—C1—C20 | 109.7 (2) | O7—C45—C44 | 121.2 (3) |
N1—C1—C19 | 102.4 (2) | N11—C45—C44 | 117.5 (3) |
C20—C1—C19 | 108.5 (2) | N11—C46—C47 | 111.8 (2) |
N1—C1—C2 | 101.9 (2) | N11—C46—H46A | 109.3 |
C20—C1—C2 | 113.6 (2) | C47—C46—H46A | 109.3 |
C19—C1—C2 | 119.5 (2) | N11—C46—H46B | 109.3 |
C21—C2—C22 | 110.3 (2) | C47—C46—H46B | 109.3 |
C21—C2—C3 | 114.3 (2) | H46A—C46—H46B | 107.9 |
C22—C2—C3 | 107.2 (2) | O11—C47—C48 | 109.1 (2) |
C21—C2—C1 | 113.1 (2) | O11—C47—C46 | 104.9 (2) |
C22—C2—C1 | 110.1 (2) | C48—C47—C46 | 112.2 (3) |
C3—C2—C1 | 101.4 (2) | O11—C47—H47 | 110.1 |
C4—C3—C24 | 110.8 (2) | C48—C47—H47 | 110.1 |
C4—C3—C2 | 101.4 (2) | C46—C47—H47 | 110.1 |
C24—C3—C2 | 118.5 (2) | C47—C48—H48A | 109.5 |
C4—C3—H3 | 108.5 | C47—C48—H48B | 109.5 |
C24—C3—H3 | 108.5 | H48A—C48—H48B | 109.5 |
C2—C3—H3 | 108.5 | C47—C48—H48C | 109.5 |
N1—C4—C5 | 124.6 (2) | H48A—C48—H48C | 109.5 |
N1—C4—C3 | 112.2 (2) | H48B—C48—H48C | 109.5 |
C5—C4—C3 | 123.2 (2) | O12—C49—N12 | 106.9 (2) |
C6—C5—C4 | 120.9 (2) | O12—C49—C50 | 106.4 (2) |
C6—C5—C27 | 123.8 (2) | N12—C49—C50 | 113.4 (2) |
C4—C5—C27 | 115.3 (2) | O12—C49—H49 | 110 |
C5—C6—N2 | 124.1 (2) | N12—C49—H49 | 110 |
C5—C6—C7 | 128.5 (2) | C50—C49—H49 | 110 |
N2—C6—C7 | 107.5 (2) | O13—C50—C51 | 111.6 (2) |
C28—C7—C6 | 117.6 (2) | O13—C50—C49 | 108.0 (2) |
C28—C7—C8 | 111.0 (2) | C51—C50—C49 | 100.5 (2) |
C6—C7—C8 | 100.4 (2) | O13—C50—H50 | 112.1 |
C28—C7—C29 | 110.8 (2) | C51—C50—H50 | 112.1 |
C6—C7—C29 | 110.9 (2) | C49—C50—H50 | 112.1 |
C8—C7—C29 | 105.0 (2) | O10—C51—C50 | 111.8 (2) |
C9—C8—C7 | 100.7 (2) | O10—C51—C52 | 110.3 (2) |
C9—C8—C31 | 110.1 (2) | C50—C51—C52 | 103.3 (2) |
C7—C8—C31 | 113.7 (2) | O10—C51—H51 | 110.4 |
C9—C8—H8 | 110.7 | C50—C51—H51 | 110.4 |
C7—C8—H8 | 110.7 | C52—C51—H51 | 110.4 |
C31—C8—H8 | 110.7 | O12—C52—C53 | 108.4 (3) |
N2—C9—C10 | 126.3 (3) | O12—C52—C51 | 104.3 (2) |
N2—C9—C8 | 110.7 (2) | C53—C52—C51 | 115.4 (3) |
C10—C9—C8 | 123.0 (2) | O12—C52—H52 | 109.5 |
C11—C10—C9 | 125.1 (3) | C53—C52—H52 | 109.5 |
C11—C10—H10 | 117.4 | C51—C52—H52 | 109.5 |
C9—C10—H10 | 117.4 | O14—C53—C52 | 112.8 (3) |
N3—C11—C10 | 124.8 (3) | O14—C53—H53A | 109 |
N3—C11—C12 | 111.9 (2) | C52—C53—H53A | 109 |
C10—C11—C12 | 123.3 (2) | O14—C53—H53B | 109 |
C11—C12—C35 | 113.0 (2) | C52—C53—H53B | 109 |
C11—C12—C34 | 108.4 (2) | H53A—C53—H53B | 107.8 |
C35—C12—C34 | 109.3 (2) | N13—C54—N12 | 114.3 (3) |
C11—C12—C13 | 100.5 (2) | N13—C54—H54 | 122.8 |
C35—C12—C13 | 116.6 (2) | N12—C54—H54 | 122.8 |
C34—C12—C13 | 108.5 (2) | C56—C55—C60 | 119.2 (3) |
C14—C13—C36 | 106.6 (2) | C56—C55—H55 | 120.4 |
C14—C13—C12 | 101.9 (2) | C60—C55—H55 | 120.4 |
C36—C13—C12 | 116.9 (2) | C55—C56—C57 | 120.2 (3) |
C14—C13—H13 | 110.3 | C55—C56—C61 | 119.6 (3) |
C36—C13—H13 | 110.3 | C57—C56—C61 | 120.3 (3) |
C12—C13—H13 | 110.3 | C58—C57—C56 | 121.1 (3) |
C15—C14—N3 | 127.1 (2) | C58—C57—C62 | 118.6 (3) |
C15—C14—C13 | 123.5 (2) | C56—C57—C62 | 120.3 (3) |
N3—C14—C13 | 109.2 (2) | C57—C58—C59 | 117.0 (3) |
C14—C15—C16 | 121.0 (2) | C57—C58—H58 | 121.5 |
C14—C15—C39 | 118.6 (2) | C59—C58—H58 | 121.5 |
C16—C15—C39 | 120.4 (2) | C60—C59—N12 | 105.9 (2) |
N4—C16—C15 | 122.3 (2) | C60—C59—C58 | 123.0 (3) |
N4—C16—C17 | 111.7 (2) | N12—C59—C58 | 131.2 (3) |
C15—C16—C17 | 125.8 (2) | C59—C60—C55 | 119.6 (3) |
C43—C17—C16 | 116.1 (2) | C59—C60—N13 | 109.6 (2) |
C43—C17—C40 | 108.5 (2) | C55—C60—N13 | 130.7 (3) |
C16—C17—C40 | 107.6 (2) | C56—C61—H61A | 109.5 |
C43—C17—C18 | 112.2 (2) | C56—C61—H61B | 109.5 |
C16—C17—C18 | 100.7 (2) | H61A—C61—H61B | 109.5 |
C40—C17—C18 | 111.6 (2) | C56—C61—H61C | 109.5 |
C19—C18—C41 | 114.0 (2) | H61A—C61—H61C | 109.5 |
C19—C18—C17 | 102.9 (2) | H61B—C61—H61C | 109.5 |
C41—C18—C17 | 115.6 (2) | C57—C62—H62A | 109.5 |
C19—C18—H18 | 108 | C57—C62—H62B | 109.5 |
C41—C18—H18 | 108 | H62A—C62—H62B | 109.5 |
C17—C18—H18 | 108 | C57—C62—H62C | 109.5 |
N4—C19—C18 | 102.9 (2) | H62A—C62—H62C | 109.5 |
N4—C19—C1 | 105.4 (2) | H62B—C62—H62C | 109.5 |
C18—C19—C1 | 121.8 (2) | C64A—C63—Co | 119.0 (3) |
N4—C19—H19 | 108.7 | C64B—C63—Co | 116.0 (4) |
C18—C19—H19 | 108.7 | C64A—C63—H63A | 107.6 |
C1—C19—H19 | 108.7 | C64B—C63—H63A | 116.9 |
C1—C20—H20A | 109.5 | Co—C63—H63A | 107.6 |
C1—C20—H20B | 109.5 | C64A—C63—H63B | 107.6 |
H20A—C20—H20B | 109.5 | C64B—C63—H63B | 100.9 |
C1—C20—H20C | 109.5 | Co—C63—H63B | 107.6 |
H20A—C20—H20C | 109.5 | H63A—C63—H63B | 107 |
H20B—C20—H20C | 109.5 | C4—N1—C1 | 112.1 (2) |
C2—C21—H21A | 109.5 | C4—N1—Co | 130.71 (19) |
C2—C21—H21B | 109.5 | C1—N1—Co | 117.19 (16) |
H21A—C21—H21B | 109.5 | C9—N2—C6 | 110.5 (2) |
C2—C21—H21C | 109.5 | C9—N2—Co | 122.65 (19) |
H21A—C21—H21C | 109.5 | C6—N2—Co | 126.73 (18) |
H21B—C21—H21C | 109.5 | C11—N3—C14 | 110.0 (2) |
C23—C22—C2 | 114.4 (2) | C11—N3—Co | 124.03 (18) |
C23—C22—H22A | 108.6 | C14—N3—Co | 125.97 (18) |
C2—C22—H22A | 108.6 | C16—N4—C19 | 111.5 (2) |
C23—C22—H22B | 108.6 | C16—N4—Co | 133.07 (19) |
C2—C22—H22B | 108.6 | C19—N4—Co | 114.79 (16) |
H22A—C22—H22B | 107.6 | C23—N5—H5A | 120 |
O1—C23—N5 | 121.9 (3) | C23—N5—H5B | 120 |
O1—C23—C22 | 121.7 (3) | H5A—N5—H5B | 120 |
N5—C23—C22 | 116.4 (3) | C26—N6—H6A | 120 |
C25—C24—C3 | 112.8 (2) | C26—N6—H6B | 120 |
C25—C24—H24A | 109 | H6A—N6—H6B | 120 |
C3—C24—H24A | 109 | C30—N7—H7A | 120 |
C25—C24—H24B | 109 | C30—N7—H7B | 120 |
C3—C24—H24B | 109 | H7A—N7—H7B | 120 |
H24A—C24—H24B | 107.8 | C33—N8—H8A | 120 |
C26—C25—C24 | 111.9 (2) | C33—N8—H8B | 120 |
C26—C25—H25A | 109.2 | H8A—N8—H8B | 120 |
C24—C25—H25A | 109.2 | C38—N9—H9A | 120 |
C26—C25—H25B | 109.2 | C38—N9—H9B | 120 |
C24—C25—H25B | 109.2 | H9A—N9—H9B | 120 |
H25A—C25—H25B | 107.9 | C42—N10—H10A | 120 |
O2—C26—N6 | 122.5 (3) | C42—N10—H10B | 120 |
O2—C26—C25 | 121.3 (3) | H10A—N10—H10B | 120 |
N6—C26—C25 | 116.2 (3) | C45—N11—C46 | 120.9 (3) |
C5—C27—H27A | 109.5 | C45—N11—H11 | 119.6 |
C5—C27—H27B | 109.5 | C46—N11—H11 | 119.6 |
H27A—C27—H27B | 109.5 | C54—N12—C59 | 106.1 (2) |
C5—C27—H27C | 109.5 | C54—N12—C49 | 125.4 (2) |
H27A—C27—H27C | 109.5 | C59—N12—C49 | 124.6 (2) |
H27B—C27—H27C | 109.5 | C54—N13—C60 | 104.0 (2) |
C7—C28—H28A | 109.5 | C54—N13—Co | 121.55 (19) |
C7—C28—H28B | 109.5 | C60—N13—Co | 134.32 (18) |
H28A—C28—H28B | 109.5 | C51—O10—P | 120.87 (17) |
C7—C28—H28C | 109.5 | C47—O11—P | 121.13 (18) |
H28A—C28—H28C | 109.5 | C49—O12—C52 | 110.0 (2) |
H28B—C28—H28C | 109.5 | C50—O13—H13A | 109.5 |
C30—C29—C7 | 117.5 (2) | C53—O14—H14 | 109.5 |
C30—C29—H29A | 107.9 | O9—P—O8 | 117.72 (12) |
C7—C29—H29A | 107.9 | O9—P—O11 | 105.40 (12) |
C30—C29—H29B | 107.9 | O8—P—O11 | 112.29 (12) |
C7—C29—H29B | 107.9 | O9—P—O10 | 111.33 (12) |
H29A—C29—H29B | 107.2 | O8—P—O10 | 108.81 (12) |
O3—C30—N7 | 122.4 (3) | O11—P—O10 | 99.82 (11) |
O3—C30—C29 | 119.2 (3) | N1—Co—N4 | 83.33 (9) |
N7—C30—C29 | 118.4 (3) | N1—Co—N2 | 90.39 (10) |
C32—C31—C8 | 113.3 (2) | N4—Co—N2 | 173.40 (10) |
C32—C31—H31A | 108.9 | N1—Co—N3 | 172.56 (10) |
C8—C31—H31A | 108.9 | N4—Co—N3 | 90.44 (9) |
C32—C31—H31B | 108.9 | N2—Co—N3 | 95.97 (10) |
C8—C31—H31B | 108.9 | N1—Co—C63 | 92.63 (11) |
H31A—C31—H31B | 107.7 | N4—Co—C63 | 90.60 (10) |
C33—C32—C31 | 117.2 (3) | N2—Co—C63 | 87.66 (10) |
C33—C32—H32A | 108 | N3—Co—C63 | 91.49 (11) |
C31—C32—H32A | 108 | N1—Co—N13 | 89.77 (9) |
C33—C32—H32B | 108 | N4—Co—N13 | 96.46 (9) |
C31—C32—H32B | 108 | N2—Co—N13 | 85.49 (9) |
H32A—C32—H32B | 107.2 | N3—Co—N13 | 86.89 (9) |
O4—C33—N8 | 120.8 (3) | C63—Co—N13 | 172.76 (10) |
O4—C33—C32 | 119.9 (3) | H1Y—O1W—H1Z | 100.6 |
N8—C33—C32 | 119.2 (3) | H2Y—O2W—H2Z | 105 |
C12—C34—H34A | 109.5 | H3Y—O3W—H3Z | 90.3 |
C12—C34—H34B | 109.5 | H4Y—O4W—H4Z | 114 |
H34A—C34—H34B | 109.5 | H5Y—O5W—H5Z | 120.8 |
C12—C34—H34C | 109.5 | H6Y—O6W—H6Z | 112.2 |
H34A—C34—H34C | 109.5 | H7Y—O7W—H7Z | 105.2 |
H34B—C34—H34C | 109.5 | H8Y—O8W—H8Z | 85.9 |
C12—C35—H35A | 109.5 | H9Y—O9W—H9Z | 123.3 |
C12—C35—H35B | 109.5 | H10Y—O10W—H10Z | 116.8 |
H35A—C35—H35B | 109.5 | H12W—O12B—H12X | 110.3 |
C12—C35—H35C | 109.5 | C63—C64A—C65A | 116.6 (5) |
H35A—C35—H35C | 109.5 | C63—C64A—H64A | 108.1 |
H35B—C35—H35C | 109.5 | C65A—C64A—H64A | 108.1 |
C37—C36—C13 | 117.3 (2) | C63—C64A—H64B | 108.1 |
C37—C36—H36A | 108 | C65A—C64A—H64B | 108.1 |
C13—C36—H36A | 108 | H64A—C64A—H64B | 107.3 |
C37—C36—H36B | 108 | C64A—C65A—C66A | 110.8 (6) |
C13—C36—H36B | 108 | C64A—C65A—C67A | 107.2 (5) |
H36A—C36—H36B | 107.2 | C66A—C65A—C67A | 109.9 (5) |
C38—C37—C36 | 112.9 (2) | C64A—C65A—H65A | 109.7 |
C38—C37—H37A | 109 | C66A—C65A—H65A | 109.7 |
C36—C37—H37A | 109 | C67A—C65A—H65A | 109.7 |
C38—C37—H37B | 109 | C63—C64B—C65B | 114.6 (14) |
C36—C37—H37B | 109 | C63—C64B—H64C | 108.6 |
H37A—C37—H37B | 107.8 | C65B—C64B—H64C | 108.6 |
O5—C38—N9 | 122.5 (3) | C63—C64B—H64D | 108.6 |
O5—C38—C37 | 120.7 (3) | C65B—C64B—H64D | 108.6 |
N9—C38—C37 | 116.8 (3) | H64C—C64B—H64D | 107.6 |
C15—C39—H39A | 109.5 | C64B—C65B—C66B | 110.7 (6) |
C15—C39—H39B | 109.5 | C64B—C65B—C67B | 107.1 (5) |
H39A—C39—H39B | 109.5 | C66B—C65B—C67B | 109.7 (5) |
C15—C39—H39C | 109.5 | C64B—C65B—H65B | 109.7 |
H39A—C39—H39C | 109.5 | C66B—C65B—H65B | 109.7 |
H39B—C39—H39C | 109.5 | C67B—C65B—H65B | 109.7 |
C17—C40—H40A | 109.5 | C65B—C66B—H66D | 109.5 |
C17—C40—H40B | 109.5 | C65B—C66B—H66E | 109.5 |
H40A—C40—H40B | 109.5 | H66D—C66B—H66E | 109.5 |
C17—C40—H40C | 109.5 | C65B—C66B—H66F | 109.5 |
H40A—C40—H40C | 109.5 | H66D—C66B—H66F | 109.5 |
H40B—C40—H40C | 109.5 | H66E—C66B—H66F | 109.5 |
C42—C41—C18 | 113.4 (2) | C65B—C67B—H67D | 109.5 |
C42—C41—H41A | 108.9 | C65B—C67B—H67E | 109.5 |
C18—C41—H41A | 108.9 | H67D—C67B—H67E | 109.5 |
C42—C41—H41B | 108.9 | C65B—C67B—H67F | 109.5 |
C18—C41—H41B | 108.9 | H67D—C67B—H67F | 109.5 |
H41A—C41—H41B | 107.7 | H67E—C67B—H67F | 109.5 |
O6—C42—N10 | 122.1 (3) | C69—C70—H70A | 109.5 |
O6—C42—C41 | 120.3 (3) | C69—C70—H70B | 109.5 |
N10—C42—C41 | 117.6 (3) | H70A—C70—H70B | 109.5 |
C44—C43—C17 | 115.8 (2) | C69—C70—H70C | 109.5 |
C44—C43—H43A | 108.3 | H70A—C70—H70C | 109.5 |
C17—C43—H43A | 108.3 | H70B—C70—H70C | 109.5 |
C44—C43—H43B | 108.3 | O15—C69—C70 | 121.1 (10) |
C17—C43—H43B | 108.3 | O15—C69—C68 | 124.6 (11) |
H43A—C43—H43B | 107.4 | C70—C69—C68 | 114.2 (9) |
C45—C44—C43 | 109.2 (2) | C69—C68—H68A | 109.5 |
C45—C44—H44A | 109.8 | C69—C68—H68B | 109.5 |
C43—C44—H44A | 109.8 | H68A—C68—H68B | 109.5 |
C45—C44—H44B | 109.8 | C69—C68—H68C | 109.5 |
C43—C44—H44B | 109.8 | H68A—C68—H68C | 109.5 |
H44A—C44—H44B | 108.3 | H68B—C68—H68C | 109.5 |
O7—C45—N11 | 121.3 (3) | ||
N1—C1—C2—C21 | 153.5 (2) | O12—C52—C53—O14 | −57.6 (3) |
C20—C1—C2—C21 | 35.5 (3) | C51—C52—C53—O14 | 58.9 (4) |
C19—C1—C2—C21 | −94.8 (3) | C60—C55—C56—C57 | −0.2 (4) |
N1—C1—C2—C22 | −82.6 (2) | C60—C55—C56—C61 | 179.9 (3) |
C20—C1—C2—C22 | 159.5 (2) | C55—C56—C57—C58 | −0.1 (5) |
C19—C1—C2—C22 | 29.2 (3) | C61—C56—C57—C58 | 179.8 (3) |
N1—C1—C2—C3 | 30.6 (2) | C55—C56—C57—C62 | 178.4 (3) |
C20—C1—C2—C3 | −87.3 (3) | C61—C56—C57—C62 | −1.7 (5) |
C19—C1—C2—C3 | 142.4 (2) | C56—C57—C58—C59 | 0.9 (4) |
C21—C2—C3—C4 | −153.0 (2) | C62—C57—C58—C59 | −177.7 (3) |
C22—C2—C3—C4 | 84.4 (2) | C57—C58—C59—C60 | −1.3 (4) |
C1—C2—C3—C4 | −31.0 (2) | C57—C58—C59—N12 | 178.6 (3) |
C21—C2—C3—C24 | −31.5 (3) | N12—C59—C60—C55 | −178.9 (2) |
C22—C2—C3—C24 | −154.1 (2) | C58—C59—C60—C55 | 1.0 (4) |
C1—C2—C3—C24 | 90.5 (3) | N12—C59—C60—N13 | 0.1 (3) |
C24—C3—C4—N1 | −105.1 (3) | C58—C59—C60—N13 | −179.9 (2) |
C2—C3—C4—N1 | 21.6 (3) | C56—C55—C60—C59 | −0.2 (4) |
C24—C3—C4—C5 | 72.5 (3) | C56—C55—C60—N13 | −179.1 (3) |
C2—C3—C4—C5 | −160.8 (2) | C5—C4—N1—C1 | −178.8 (2) |
N1—C4—C5—C6 | 9.4 (4) | C3—C4—N1—C1 | −1.3 (3) |
C3—C4—C5—C6 | −167.9 (3) | C5—C4—N1—Co | 3.5 (4) |
N1—C4—C5—C27 | −170.1 (3) | C3—C4—N1—Co | −178.98 (18) |
C3—C4—C5—C27 | 12.6 (4) | C20—C1—N1—C4 | 101.3 (3) |
C4—C5—C6—N2 | −5.7 (4) | C19—C1—N1—C4 | −143.6 (2) |
C27—C5—C6—N2 | 173.7 (3) | C2—C1—N1—C4 | −19.4 (3) |
C4—C5—C6—C7 | 174.6 (3) | C20—C1—N1—Co | −80.6 (2) |
C27—C5—C6—C7 | −6.0 (5) | C19—C1—N1—Co | 34.5 (2) |
C5—C6—C7—C28 | −36.1 (4) | C2—C1—N1—Co | 158.65 (16) |
N2—C6—C7—C28 | 144.2 (2) | C10—C9—N2—C6 | 164.4 (3) |
C5—C6—C7—C8 | −156.6 (3) | C8—C9—N2—C6 | −14.8 (3) |
N2—C6—C7—C8 | 23.7 (3) | C10—C9—N2—Co | −12.6 (4) |
C5—C6—C7—C29 | 92.9 (3) | C8—C9—N2—Co | 168.27 (18) |
N2—C6—C7—C29 | −86.8 (3) | C5—C6—N2—C9 | 173.5 (3) |
C28—C7—C8—C9 | −155.0 (2) | C7—C6—N2—C9 | −6.7 (3) |
C6—C7—C8—C9 | −29.9 (2) | C5—C6—N2—Co | −9.7 (4) |
C29—C7—C8—C9 | 85.3 (2) | C7—C6—N2—Co | 170.07 (17) |
C28—C7—C8—C31 | −37.3 (3) | C10—C11—N3—C14 | 172.2 (3) |
C6—C7—C8—C31 | 87.8 (2) | C12—C11—N3—C14 | −8.9 (3) |
C29—C7—C8—C31 | −157.1 (2) | C10—C11—N3—Co | −6.5 (4) |
C7—C8—C9—N2 | 29.2 (3) | C12—C11—N3—Co | 172.32 (18) |
C31—C8—C9—N2 | −91.2 (3) | C15—C14—N3—C11 | 176.7 (3) |
C7—C8—C9—C10 | −150.0 (3) | C13—C14—N3—C11 | −8.5 (3) |
C31—C8—C9—C10 | 89.6 (3) | C15—C14—N3—Co | −4.5 (4) |
N2—C9—C10—C11 | 5.6 (5) | C13—C14—N3—Co | 170.26 (18) |
C8—C9—C10—C11 | −175.3 (3) | C15—C16—N4—C19 | −171.4 (2) |
C9—C10—C11—N3 | 5.0 (5) | C17—C16—N4—C19 | 3.5 (3) |
C9—C10—C11—C12 | −173.7 (3) | C15—C16—N4—Co | −1.0 (4) |
N3—C11—C12—C35 | 146.5 (2) | C17—C16—N4—Co | 173.90 (18) |
C10—C11—C12—C35 | −34.6 (4) | C18—C19—N4—C16 | −22.5 (3) |
N3—C11—C12—C34 | −92.1 (3) | C1—C19—N4—C16 | −151.2 (2) |
C10—C11—C12—C34 | 86.7 (3) | C18—C19—N4—Co | 165.15 (16) |
N3—C11—C12—C13 | 21.6 (3) | C1—C19—N4—Co | 36.5 (2) |
C10—C11—C12—C13 | −159.6 (3) | O7—C45—N11—C46 | −2.8 (4) |
C11—C12—C13—C14 | −24.0 (3) | C44—C45—N11—C46 | 179.1 (3) |
C35—C12—C13—C14 | −146.4 (2) | C47—C46—N11—C45 | −82.5 (3) |
C34—C12—C13—C14 | 89.7 (3) | N13—C54—N12—C59 | −3.7 (3) |
C11—C12—C13—C36 | 91.8 (3) | N13—C54—N12—C49 | −162.1 (3) |
C35—C12—C13—C36 | −30.7 (3) | C60—C59—N12—C54 | 2.0 (3) |
C34—C12—C13—C36 | −154.6 (2) | C58—C59—N12—C54 | −178.0 (3) |
C36—C13—C14—C15 | 73.3 (3) | C60—C59—N12—C49 | 160.6 (3) |
C12—C13—C14—C15 | −163.7 (3) | C58—C59—N12—C49 | −19.3 (5) |
C36—C13—C14—N3 | −101.8 (3) | O12—C49—N12—C54 | −47.0 (3) |
C12—C13—C14—N3 | 21.3 (3) | C50—C49—N12—C54 | 69.9 (3) |
N3—C14—C15—C16 | 2.2 (4) | O12—C49—N12—C59 | 158.4 (2) |
C13—C14—C15—C16 | −171.9 (2) | C50—C49—N12—C59 | −84.7 (3) |
N3—C14—C15—C39 | −176.9 (3) | N12—C54—N13—C60 | 3.7 (3) |
C13—C14—C15—C39 | 9.0 (4) | N12—C54—N13—Co | −172.91 (17) |
C14—C15—C16—N4 | 0.7 (4) | C59—C60—N13—C54 | −2.2 (3) |
C39—C15—C16—N4 | 179.8 (2) | C55—C60—N13—C54 | 176.7 (3) |
C14—C15—C16—C17 | −173.5 (3) | C59—C60—N13—Co | 173.70 (18) |
C39—C15—C16—C17 | 5.6 (4) | C55—C60—N13—Co | −7.4 (4) |
N4—C16—C17—C43 | 137.9 (2) | C50—C51—O10—P | 123.0 (2) |
C15—C16—C17—C43 | −47.3 (4) | C52—C51—O10—P | −122.6 (2) |
N4—C16—C17—C40 | −100.3 (3) | C48—C47—O11—P | −102.8 (3) |
C15—C16—C17—C40 | 74.4 (3) | C46—C47—O11—P | 136.8 (2) |
N4—C16—C17—C18 | 16.6 (3) | N12—C49—O12—C52 | 135.3 (2) |
C15—C16—C17—C18 | −168.7 (2) | C50—C49—O12—C52 | 13.9 (3) |
C43—C17—C18—C19 | −152.7 (2) | C53—C52—O12—C49 | 134.5 (2) |
C16—C17—C18—C19 | −28.7 (2) | C51—C52—O12—C49 | 11.1 (3) |
C40—C17—C18—C19 | 85.2 (3) | C47—O11—P—O9 | −177.44 (19) |
C43—C17—C18—C41 | 82.4 (3) | C47—O11—P—O8 | 53.2 (2) |
C16—C17—C18—C41 | −153.6 (2) | C47—O11—P—O10 | −61.9 (2) |
C40—C17—C18—C41 | −39.7 (3) | C51—O10—P—O9 | −84.4 (2) |
C41—C18—C19—N4 | 157.1 (2) | C51—O10—P—O8 | 47.0 (2) |
C17—C18—C19—N4 | 31.2 (2) | C51—O10—P—O11 | 164.7 (2) |
C41—C18—C19—C1 | −85.4 (3) | C4—N1—Co—N4 | 164.6 (3) |
C17—C18—C19—C1 | 148.8 (2) | C1—N1—Co—N4 | −13.05 (18) |
N1—C1—C19—N4 | −41.6 (2) | C4—N1—Co—N2 | −13.4 (2) |
C20—C1—C19—N4 | 74.3 (3) | C1—N1—Co—N2 | 168.98 (18) |
C2—C1—C19—N4 | −153.2 (2) | C4—N1—Co—C63 | 74.3 (3) |
N1—C1—C19—C18 | −157.9 (2) | C1—N1—Co—C63 | −103.34 (19) |
C20—C1—C19—C18 | −42.0 (3) | C4—N1—Co—N13 | −98.9 (2) |
C2—C1—C19—C18 | 90.5 (3) | C1—N1—Co—N13 | 83.49 (18) |
C21—C2—C22—C23 | −66.8 (3) | C16—N4—Co—N1 | 175.2 (3) |
C3—C2—C22—C23 | 58.2 (3) | C19—N4—Co—N1 | −14.61 (18) |
C1—C2—C22—C23 | 167.7 (2) | C16—N4—Co—N3 | −0.7 (3) |
C2—C22—C23—O1 | 61.8 (4) | C19—N4—Co—N3 | 169.47 (18) |
C2—C22—C23—N5 | −118.8 (3) | C16—N4—Co—C63 | −92.2 (3) |
C4—C3—C24—C25 | −155.5 (2) | C19—N4—Co—C63 | 77.98 (19) |
C2—C3—C24—C25 | 87.9 (3) | C16—N4—Co—N13 | 86.2 (3) |
C3—C24—C25—C26 | 171.0 (2) | C19—N4—Co—N13 | −103.61 (18) |
C24—C25—C26—O2 | −90.6 (4) | C9—N2—Co—N1 | −167.5 (2) |
C24—C25—C26—N6 | 90.8 (3) | C6—N2—Co—N1 | 16.0 (2) |
C28—C7—C29—C30 | 84.6 (3) | C9—N2—Co—N3 | 8.6 (2) |
C6—C7—C29—C30 | −47.9 (3) | C6—N2—Co—N3 | −167.8 (2) |
C8—C7—C29—C30 | −155.5 (2) | C9—N2—Co—C63 | 99.9 (2) |
C7—C29—C30—O3 | 99.7 (3) | C6—N2—Co—C63 | −76.6 (2) |
C7—C29—C30—N7 | −82.8 (3) | C9—N2—Co—N13 | −77.8 (2) |
C9—C8—C31—C32 | −49.9 (3) | C6—N2—Co—N13 | 105.8 (2) |
C7—C8—C31—C32 | −162.0 (2) | C11—N3—Co—N4 | −178.2 (2) |
C8—C31—C32—C33 | 178.0 (2) | C14—N3—Co—N4 | 3.2 (2) |
C31—C32—C33—O4 | −168.6 (3) | C11—N3—Co—N2 | 0.2 (2) |
C31—C32—C33—N8 | 12.2 (4) | C14—N3—Co—N2 | −178.3 (2) |
C14—C13—C36—C37 | −170.6 (2) | C11—N3—Co—C63 | −87.6 (2) |
C12—C13—C36—C37 | 76.2 (3) | C14—N3—Co—C63 | 93.9 (2) |
C13—C36—C37—C38 | 41.4 (4) | C11—N3—Co—N13 | 85.3 (2) |
C36—C37—C38—O5 | −106.7 (3) | C14—N3—Co—N13 | −93.2 (2) |
C36—C37—C38—N9 | 72.7 (3) | C64A—C63—Co—N1 | 129.8 (7) |
C19—C18—C41—C42 | 175.2 (2) | C64B—C63—Co—N1 | 119.3 (10) |
C17—C18—C41—C42 | −65.9 (3) | C64A—C63—Co—N4 | 46.4 (7) |
C18—C41—C42—O6 | −53.4 (4) | C64B—C63—Co—N4 | 36.0 (10) |
C18—C41—C42—N10 | 127.1 (3) | C64A—C63—Co—N2 | −139.9 (7) |
C16—C17—C43—C44 | −49.2 (3) | C64B—C63—Co—N2 | −150.4 (10) |
C40—C17—C43—C44 | −170.5 (2) | C64A—C63—Co—N3 | −44.0 (7) |
C18—C17—C43—C44 | 65.7 (3) | C64B—C63—Co—N3 | −54.5 (10) |
C17—C43—C44—C45 | 161.5 (2) | C54—N13—Co—N1 | −137.1 (2) |
C43—C44—C45—O7 | −63.8 (4) | C60—N13—Co—N1 | 47.6 (2) |
C43—C44—C45—N11 | 114.3 (3) | C54—N13—Co—N4 | −53.8 (2) |
N11—C46—C47—O11 | −63.3 (3) | C60—N13—Co—N4 | 130.8 (2) |
N11—C46—C47—C48 | 178.3 (3) | C54—N13—Co—N2 | 132.5 (2) |
O12—C49—C50—O13 | 84.2 (3) | C60—N13—Co—N2 | −42.8 (2) |
N12—C49—C50—O13 | −33.0 (3) | C54—N13—Co—N3 | 36.3 (2) |
O12—C49—C50—C51 | −32.8 (3) | C60—N13—Co—N3 | −139.1 (2) |
N12—C49—C50—C51 | −150.0 (2) | C64B—C63—C64A—C65A | −96 (3) |
O13—C50—C51—O10 | 43.1 (3) | Co—C63—C64A—C65A | −170.6 (7) |
C49—C50—C51—O10 | 157.3 (2) | C63—C64A—C65A—C66A | 75.6 (11) |
O13—C50—C51—C52 | −75.5 (3) | C63—C64A—C65A—C67A | −164.6 (10) |
C49—C50—C51—C52 | 38.7 (3) | C64A—C63—C64B—C65B | 39 (2) |
O10—C51—C52—O12 | −151.3 (2) | Co—C63—C64B—C65B | 149.5 (6) |
C50—C51—C52—O12 | −31.7 (3) | C63—C64B—C65B—C66B | 51.8 (12) |
O10—C51—C52—C53 | 90.0 (3) | C63—C64B—C65B—C67B | 171.5 (12) |
C50—C51—C52—C53 | −150.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5A···O9W | 0.88 | 2.23 | 3.085 (4) | 165 |
N5—H5B···O8W | 0.88 | 2.21 | 3.025 (4) | 153 |
N6—H6A···O12Ai | 0.88 | 2.33 | 3.101 (6) | 147 |
N6—H6B···O9ii | 0.88 | 2.05 | 2.931 (4) | 179 |
N7—H7A···O7W | 0.88 | 2.17 | 3.020 (4) | 163 |
N7—H7B···O5Wiii | 0.88 | 2.12 | 2.891 (4) | 146 |
N8—H8B···O1iii | 0.88 | 2.16 | 2.948 (3) | 148 |
N9—H9A···O1iv | 0.88 | 2.2 | 3.020 (3) | 154 |
N9—H9B···O2Wiv | 0.88 | 1.97 | 2.843 (4) | 170 |
N10—H10A···O5v | 0.88 | 2.16 | 3.021 (3) | 165 |
N10—H10B···O2vi | 0.88 | 2.01 | 2.862 (4) | 162 |
N11—H11···O12Bvii | 0.88 | 2.15 | 3.025 (8) | 171 |
N11—H11···O12Avii | 0.88 | 2.23 | 3.097 (5) | 167 |
O13—H13A···O1Wvii | 0.84 | 1.87 | 2.705 (3) | 178 |
O14—H14···O6Wviii | 0.84 | 1.93 | 2.759 (3) | 168 |
O1W—H1Y···O8ix | 0.85 | 1.84 | 2.687 (3) | 180 |
O1W—H1Z···O12B | 0.85 | 1.81 | 2.664 (8) | 179 |
O2W—H2Y···O7x | 0.85 | 1.96 | 2.810 (3) | 180 |
O2W—H2Z···O3Wxi | 0.85 | 1.93 | 2.780 (3) | 180 |
O3W—H3Y···O9xii | 0.85 | 1.86 | 2.715 (3) | 180 |
O3W—H3Z···O1Wxiii | 0.85 | 2.06 | 2.906 (3) | 180 |
O4W—H4Y···O4xiv | 0.85 | 1.93 | 2.777 (3) | 180 |
O4W—H4Z···O12xiv | 0.85 | 2.19 | 3.036 (3) | 180 |
O5W—H5Y···O6 | 0.85 | 1.93 | 2.780 (3) | 179 |
O5W—H5Z···O8ii | 0.85 | 1.85 | 2.699 (3) | 178 |
O6W—H6Y···O4W | 0.85 | 1.92 | 2.770 (4) | 179 |
O6W—H6Z···O2xv | 0.85 | 2.14 | 2.987 (4) | 180 |
O7W—H7Y···O6Wxvi | 0.85 | 2.07 | 2.919 (4) | 180 |
O7W—H7Z···O10Wiii | 0.85 | 2 | 2.856 (5) | 179 |
O8W—H8Y···O3 | 0.85 | 1.94 | 2.788 (4) | 180 |
O8W—H8Z···O7W | 0.85 | 2.06 | 2.911 (4) | 180 |
O9W—H9Y···O11Wiii | 0.85 | 2.1 | 2.948 (5) | 180 |
O9W—H9Z···O5x | 0.85 | 1.99 | 2.836 (4) | 180 |
O10W—H10Y···O6 | 0.85 | 1.97 | 2.823 (4) | 179 |
O10W—H10Z···O13Wxvii | 0.85 | 2.06 | 2.908 (15) | 179 |
O12B—H12W···O14ix | 0.85 | 2.04 | 2.886 (8) | 180 |
O12B—H12X···O6xi | 0.85 | 2.13 | 2.981 (8) | 180 |
Symmetry codes: (i) x, y, z+1; (ii) x−1/2, −y+1/2, −z+2; (iii) −x+1, y−1/2, −z+3/2; (iv) x+1, y, z; (v) −x+2, y+1/2, −z+3/2; (vi) −x+1, y+1/2, −z+3/2; (vii) x+1/2, −y+1/2, −z+1; (viii) x+1, y−1, z; (ix) x−1, y, z−1; (x) x−1, y, z; (xi) x−1/2, −y+1/2, −z+1; (xii) x, y, z−1; (xiii) x+1/2, −y+1/2, −z; (xiv) x−1, y+1, z; (xv) x, y+1, z; (xvi) −x+1/2, −y+1, z−1/2; (xvii) −x+3/2, −y+1, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Co(C5H11)(C62H88N13O14P)]·0.385C3H6O·12.650H2O |
Mr | 1650.69 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 123 |
a, b, c (Å) | 15.959 (3), 20.793 (4), 24.403 (5) |
V (Å3) | 8098 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.32 |
Crystal size (mm) | 0.48 × 0.26 × 0.26 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.863, 0.922 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 45443, 16502, 14388 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.107, 1.05 |
No. of reflections | 16502 |
No. of parameters | 1085 |
No. of restraints | 45 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.59, −0.44 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881, 7369 Friedel pairs. |
Absolute structure parameter | 0.010 (10) |
Computer programs: SMART (Bruker,1998), SMART, SAINT (Bruker,1999), SHELXTL (Bruker,1999), SHELXTL, ORTEP-3 (Farrugia,1997).
C63—C64A | 1.454 (10) | N2—Co | 1.914 (2) |
C63—C64B | 1.506 (18) | N3—Co | 1.915 (2) |
C63—Co | 2.044 (3) | N4—Co | 1.889 (2) |
N1—Co | 1.869 (2) | N13—Co | 2.277 (2) |
C64A—C63—Co | 119.0 (3) | C64B—C63—Co | 116.0 (4) |
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Cobalamins (derivatives of vitamin B12) contain a six coordinate cobalt(III) atom coordinated equatorially by four pyrrole N atoms of a corrin ligand. The lower (α) axial ligand is 5,6-dimethylbenzimidazole-α-D-ribofuranose-3'-phosphate (DMB), while the upper (β) ligand, R, is variable (R = CN− in B12 itself). Adenosylcobalamin (AdoCbl; R = 5'-deoxyadenosyl) and methylcobalamin (MeCbl; R = CH3−) function as coenzymes in a number of biologically important 1,2 rearrangement and transmethylation reactions, respectively (Ludwig et al., 1999). The first step in the AdoCbl-dependent enzymes is homolytic cleavage of the Co—C bond to produce a CoII ion and an Ado radical (Marsh, 1999). The means by which the enzyme activates the Co—C bond in AdoCbl for homolytic cleavage by a factor of 109–1012 (Hay & Finke, 1986; Brown & Li, 1998) remains unclear. The rate enhancement may be caused either by an upward conformational distortion of the corrin ring, induced by steric interactions with the large DMB base (Halpern, 1985; Hay et al., 1987; Pett et al., 1987), or by the enzyme directly lengthening the Co—C bond or distorting the Co—C—C angle (Williams, 1995). Electronic effects of the trans ligand may also play a role in activating the Co—C bond for homolysis (Pratt, 1999). The trans influence refers to the effect that the β ligand has on the length of the Co—DMB(N13) bond.
We have determined the X-ray crystal structure of isoamylcobalamin (isoamylCbl), (I) (Fig. 1), a structural analogue of AdoCbl and MeCbl, in order to compare the ground-state trans influence of the C5H11− ligand to the β ligands in other cobalamin derivatives.
Compound (I) crystallizes in the orthorhombic space group P212121 and is isomorphous with the other cobalamin derivatives belonging to packing type I (Gruber et al., 1998). Selected bond lengths and bond angles involving the coordination sphere of the metal ion are listed in Table 1. The β alkyl ligand is disordered over two slightly different positions; in the first position [0.615 (4) occupancy], atom C65A points directly towards the c side chain, whereas in the second position [0.385 (4) occupancy], atom C65B points towards atom C10 when viewed from above the corrin ring. The β Co—C bond length [2.044 (3) Å] is longer than the corresponding bond length for MeCbl (Randaccio et al., 2000; Rossi et al., 1985) [average for two MeCbl structures = 1.984 (7) Å], and is also slightly longer than the corresponding bond length in AdoCbl (Bouquiere et al., 1993; Savage et al., 1987) [average for four AdoCbl structures = 2.01 (3) Å]. The Co—N13 bond length [2.277 (2) Å] is substantially longer than that observed in MeCbl [mean for two structures = 2.18 (2) Å] and slightly longer than that in AdoCbl [average for four structures = 2.23 (2) Å], and is the second longest Co—N13 bond length ever reported for a cobalamin structure, the longest being for (S)-2,3-dihydroxypropyl-cobalamin (2.367 Å; Alcock et al., 1985). The isoamyl group clearly is a strong σ-donor (comparable to the Ado group of AdoCbl) and markedly lengthens the trans Co—N13 bond. The Co—C—C angle [119.0 (3) or 116.0 (4)°] is slightly smaller than that observed for AdoCbl [mean for four structures = 122 (2)°], where there is steric pressure exerted on the adenine moiety by the C34 methyl group (Alcock et al., 1985). The six amide side chains are extensively hydrogen bonded to either solvent water molecules, or the side chains of symmetry-related molecules. This hydrogen-bonding scheme is similar to that seen for other cobalamin molecules belonging to packing type I.
The corrin fold angle, defined as the angle between the normals of the two least-squares planes passing through atoms N1, C4, C5, C6, N2, C9 and C10 (plane 1), and C10, C11, N3, C14, C15, C16 and N4 (plane 2), is calculated to be 10.57°. This angle is less than the fold angles for both MeCbl (14.72°) and AdoCbl [mean for four structures = 13.4 (6)°], and reflects the long Co—N13 bond.