Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106028101/gz3025sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270106028101/gz3025Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270106028101/gz3025IIsup3.hkl |
CCDC references: 621295; 621296
Compounds (I) and (II) were synthesized by the conventional liquid phase method, and purified by silica gel column chromatography. Crystals were grown from methanol and ethyl acetate solutions.
H atoms were placed at calculated positions (C—H = 0.95–1.00 A and N—H = 0.88 A), with isotropic displacement parameters [Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(parent atom) for all other atoms], and included in the structure-factor calculation. H atoms of hydroxy groups were found in a differential Fourier map considering the hydrogen-bonding network, and refined. Restraints for displacement parameters were applied for (I) and (II) using SIMU and DELU instructions of SHELXL97 (Sheldrick, 1997). In the absence of significant anomalous scattering effects, Friedel pairs were merged, and the absolute configuration is assumed from that of the starting material.
For both compounds, data collection: SMART (Bruker, 1998). Cell refinement: SAINT-Plus (Bruker, 1998) for (I); SMART for (II). For both compounds, data reduction: SAINT-Plus (Bruker, 1998). Program(s) used to solve structure: SHELXS97 (Sheldrick, 1990) for (I); SHELXD (Sheldrick & Gould, 1995) for (II). For both compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
C24H33N3O7 | F(000) = 1016 |
Mr = 475.53 | Dx = 1.246 Mg m−3 |
MonoclinicP21 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.922 (2) Å | Cell parameters from 8042 reflections |
b = 15.208 (3) Å | θ = 2.3–28.3° |
c = 18.692 (4) Å | µ = 0.09 mm−1 |
β = 91.523 (3)° | T = 200 K |
V = 2535.1 (9) Å3 | Plate, colorless |
Z = 4 | 0.45 × 0.30 × 0.08 mm |
Bruker SMART APEX area-detector diffractometer | 5790 independent reflections |
Radiation source: MacScience, M18XCE rotating anode | 4804 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 8.366 pixels mm-1 | θmax = 27.1°, θmin = 2.2° |
ω–scan | h = −11→11 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −19→19 |
Tmin = 0.883, Tmax = 0.993 | l = −22→23 |
21865 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.162 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0823P)2 + 1.2083P] where P = (Fo2 + 2Fc2)/3 |
5790 reflections | (Δ/σ)max = 0.004 |
627 parameters | Δρmax = 0.51 e Å−3 |
279 restraints | Δρmin = −0.46 e Å−3 |
C24H33N3O7 | V = 2535.1 (9) Å3 |
Mr = 475.53 | Z = 4 |
MonoclinicP21 | Mo Kα radiation |
a = 8.922 (2) Å | µ = 0.09 mm−1 |
b = 15.208 (3) Å | T = 200 K |
c = 18.692 (4) Å | 0.45 × 0.30 × 0.08 mm |
β = 91.523 (3)° |
Bruker SMART APEX area-detector diffractometer | 5790 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 4804 reflections with I > 2σ(I) |
Tmin = 0.883, Tmax = 0.993 | Rint = 0.028 |
21865 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 279 restraints |
wR(F2) = 0.162 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.51 e Å−3 |
5790 reflections | Δρmin = −0.46 e Å−3 |
627 parameters |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C10A | 0.1898 (7) | 0.7171 (4) | 0.8541 (3) | 0.0615 (9) | |
C11A | 0.2185 (10) | 0.7811 (5) | 0.9146 (4) | 0.0784 (14) | |
H11A | 0.3153 | 0.7677 | 0.9381 | 0.118* | |
H12A | 0.1387 | 0.7759 | 0.9493 | 0.118* | |
H13A | 0.2203 | 0.8411 | 0.8956 | 0.118* | |
C12A | 0.1916 (9) | 0.6225 (4) | 0.8802 (4) | 0.0721 (13) | |
H14A | 0.1785 | 0.5828 | 0.8392 | 0.108* | |
H15A | 0.1098 | 0.6136 | 0.9134 | 0.108* | |
H16A | 0.2877 | 0.6102 | 0.9048 | 0.108* | |
C13A | 0.0475 (8) | 0.7352 (5) | 0.8119 (4) | 0.0743 (13) | |
H17A | 0.0425 | 0.7979 | 0.7997 | 0.111* | |
H18A | −0.0389 | 0.7195 | 0.8405 | 0.111* | |
H19A | 0.0461 | 0.7002 | 0.7678 | 0.111* | |
O10A | 0.3186 (4) | 0.7175 (2) | 0.8062 (2) | 0.0545 (7) | |
C14A | 0.3547 (6) | 0.7912 (3) | 0.7710 (3) | 0.0473 (9) | |
O14A | 0.2909 (4) | 0.8618 (2) | 0.77444 (19) | 0.0521 (9) | |
N20A | 0.4764 (5) | 0.7774 (3) | 0.7314 (2) | 0.0428 (7) | |
C20A | 0.5264 (5) | 0.8455 (3) | 0.6829 (3) | 0.0407 (7) | |
H20A | 0.5411 | 0.9028 | 0.7084 | 0.049* | |
C21A | 0.6771 (6) | 0.8082 (3) | 0.6573 (3) | 0.0482 (8) | |
H21A | 0.6996 | 0.8297 | 0.6088 | 0.058* | |
H22A | 0.7607 | 0.8241 | 0.6906 | 0.058* | |
C22A | 0.6494 (6) | 0.7098 (4) | 0.6571 (3) | 0.0530 (8) | |
H23A | 0.7452 | 0.6769 | 0.6600 | 0.064* | |
H24A | 0.5926 | 0.6915 | 0.6134 | 0.064* | |
C23A | 0.5581 (6) | 0.6946 (3) | 0.7236 (3) | 0.0492 (8) | |
H25A | 0.4882 | 0.6446 | 0.7168 | 0.059* | |
H26A | 0.6241 | 0.6831 | 0.7660 | 0.059* | |
C24A | 0.4190 (4) | 0.8553 (3) | 0.6189 (2) | 0.0308 (8) | |
O24A | 0.3301 (4) | 0.7964 (2) | 0.60153 (18) | 0.0420 (7) | |
N30A | 0.4309 (4) | 0.9286 (2) | 0.58009 (18) | 0.0317 (7) | |
C30A | 0.3524 (4) | 0.9366 (3) | 0.5105 (2) | 0.0293 (8) | |
H30A | 0.2442 | 0.9204 | 0.5138 | 0.035* | |
C31A | 0.3711 (5) | 1.0344 (3) | 0.4919 (2) | 0.0348 (9) | |
H33A | 0.3724 | 1.0432 | 0.4395 | 0.042* | |
H34A | 0.2891 | 1.0699 | 0.5118 | 0.042* | |
C32A | 0.5211 (5) | 1.0585 (3) | 0.5267 (2) | 0.0358 (9) | |
H35A | 0.6044 | 1.0420 | 0.4946 | 0.043* | |
O32A | 0.5263 (5) | 1.1497 (2) | 0.5416 (2) | 0.0506 (9) | |
H32A | 0.608 (9) | 1.159 (6) | 0.558 (4) | 0.08 (2)* | |
C33A | 0.5297 (5) | 1.0032 (3) | 0.5953 (2) | 0.0378 (9) | |
H36A | 0.6336 | 0.9832 | 0.6056 | 0.045* | |
H37A | 0.4944 | 1.0373 | 0.6368 | 0.045* | |
C34A | 0.4299 (4) | 0.8809 (3) | 0.4547 (2) | 0.0314 (8) | |
O34A | 0.5656 (3) | 0.8718 (2) | 0.45508 (18) | 0.0442 (8) | |
N40A | 0.3379 (4) | 0.8482 (2) | 0.40296 (18) | 0.0323 (7) | |
H40A | 0.2400 | 0.8505 | 0.4074 | 0.039* | |
C40A | 0.4018 (5) | 0.8091 (3) | 0.3400 (2) | 0.0352 (9) | |
H41A | 0.3223 | 0.7772 | 0.3127 | 0.042* | |
H42A | 0.4793 | 0.7658 | 0.3551 | 0.042* | |
C41A | 0.4713 (5) | 0.8767 (3) | 0.2920 (2) | 0.0376 (9) | |
O41A | 0.4710 (4) | 0.9544 (2) | 0.30004 (18) | 0.0460 (8) | |
C51A | 0.6730 (7) | 0.8343 (4) | 0.1295 (3) | 0.0631 (9) | |
C52A | 0.6511 (8) | 0.8494 (5) | 0.0573 (3) | 0.0724 (10) | |
H52A | 0.5841 | 0.8940 | 0.0409 | 0.087* | |
C53A | 0.7284 (9) | 0.7985 (5) | 0.0086 (4) | 0.0793 (10) | |
H53A | 0.7161 | 0.8100 | −0.0411 | 0.095* | |
C54A | 0.8207 (9) | 0.7330 (5) | 0.0308 (4) | 0.0791 (10) | |
H54A | 0.8724 | 0.6992 | −0.0035 | 0.095* | |
C55A | 0.8402 (8) | 0.7150 (5) | 0.1013 (4) | 0.0756 (10) | |
H55A | 0.9040 | 0.6683 | 0.1166 | 0.091* | |
C56A | 0.7655 (8) | 0.7658 (5) | 0.1511 (4) | 0.0685 (9) | |
H56A | 0.7783 | 0.7532 | 0.2007 | 0.082* | |
C57A | 0.6005 (7) | 0.8920 (4) | 0.1836 (3) | 0.0593 (10) | |
H57A | 0.6760 | 0.9316 | 0.2062 | 0.071* | |
H58A | 0.5215 | 0.9285 | 0.1601 | 0.071* | |
O57A | 0.5353 (4) | 0.8356 (2) | 0.23733 (18) | 0.0507 (9) | |
C10B | 0.3631 (8) | 0.5902 (5) | 0.1387 (4) | 0.0745 (10) | |
C11B | 0.3932 (10) | 0.5070 (6) | 0.0961 (5) | 0.0968 (17) | |
H11B | 0.3969 | 0.4563 | 0.1285 | 0.145* | |
H12B | 0.4892 | 0.5126 | 0.0723 | 0.145* | |
H13B | 0.3126 | 0.4985 | 0.0601 | 0.145* | |
C12B | 0.4851 (8) | 0.6046 (6) | 0.1940 (4) | 0.0790 (14) | |
H14B | 0.4632 | 0.6576 | 0.2216 | 0.119* | |
H15B | 0.5811 | 0.6118 | 0.1704 | 0.119* | |
H16B | 0.4907 | 0.5538 | 0.2262 | 0.119* | |
C13B | 0.3363 (10) | 0.6696 (6) | 0.0899 (4) | 0.0915 (16) | |
H17B | 0.2421 | 0.6617 | 0.0624 | 0.137* | |
H18B | 0.4194 | 0.6750 | 0.0569 | 0.137* | |
H19B | 0.3303 | 0.7230 | 0.1190 | 0.137* | |
O10B | 0.2244 (5) | 0.5675 (3) | 0.1750 (2) | 0.0666 (9) | |
C14B | 0.1577 (7) | 0.6243 (4) | 0.2184 (3) | 0.0568 (10) | |
O14B | 0.1849 (5) | 0.7025 (2) | 0.22351 (19) | 0.0548 (9) | |
N20B | 0.0521 (5) | 0.5825 (3) | 0.2557 (2) | 0.0493 (8) | |
C20B | −0.0284 (6) | 0.6293 (4) | 0.3101 (3) | 0.0505 (8) | |
H20B | −0.0782 | 0.6832 | 0.2902 | 0.061* | |
C21B | −0.1448 (7) | 0.5589 (4) | 0.3304 (3) | 0.0591 (9) | |
H21B | −0.1797 | 0.5682 | 0.3797 | 0.071* | |
H22B | −0.2324 | 0.5597 | 0.2968 | 0.071* | |
C22B | −0.0588 (7) | 0.4737 (4) | 0.3247 (3) | 0.0608 (9) | |
H23B | 0.0067 | 0.4641 | 0.3676 | 0.073* | |
H24B | −0.1277 | 0.4230 | 0.3189 | 0.073* | |
C23B | 0.0321 (7) | 0.4864 (4) | 0.2593 (3) | 0.0564 (8) | |
H25B | 0.1300 | 0.4561 | 0.2642 | 0.068* | |
H26B | −0.0220 | 0.4641 | 0.2160 | 0.068* | |
C24B | 0.0710 (4) | 0.6507 (3) | 0.3754 (2) | 0.0310 (8) | |
O24B | 0.1973 (3) | 0.6196 (2) | 0.38248 (17) | 0.0379 (7) | |
N30B | 0.0105 (4) | 0.7009 (2) | 0.42616 (18) | 0.0284 (7) | |
C30B | 0.0859 (4) | 0.7103 (2) | 0.4962 (2) | 0.0261 (7) | |
H30B | 0.1883 | 0.7356 | 0.4903 | 0.031* | |
C31B | −0.0138 (5) | 0.7770 (3) | 0.5351 (2) | 0.0349 (9) | |
H33B | −0.0894 | 0.7467 | 0.5641 | 0.042* | |
H34B | 0.0472 | 0.8162 | 0.5666 | 0.042* | |
C32B | −0.0877 (5) | 0.8280 (3) | 0.4740 (2) | 0.0341 (9) | |
H35B | −0.1801 | 0.8592 | 0.4894 | 0.041* | |
O32B | 0.0170 (3) | 0.8873 (2) | 0.44220 (18) | 0.0361 (7) | |
H32B | −0.002 (7) | 0.932 (5) | 0.456 (3) | 0.051 (17)* | |
C33B | −0.1240 (5) | 0.7568 (3) | 0.4193 (3) | 0.0374 (9) | |
H36B | −0.2158 | 0.7241 | 0.4314 | 0.045* | |
H37B | −0.1360 | 0.7814 | 0.3704 | 0.045* | |
C34B | 0.0976 (4) | 0.6228 (3) | 0.5362 (2) | 0.0285 (8) | |
O34B | 0.0298 (4) | 0.55642 (18) | 0.51501 (17) | 0.0380 (7) | |
N40B | 0.1823 (4) | 0.6256 (2) | 0.59588 (19) | 0.0337 (7) | |
H40B | 0.2316 | 0.6741 | 0.6067 | 0.040* | |
C40B | 0.1953 (5) | 0.5504 (3) | 0.6437 (2) | 0.0361 (9) | |
H41B | 0.2729 | 0.5628 | 0.6812 | 0.043* | |
H42B | 0.2283 | 0.4985 | 0.6163 | 0.043* | |
C41B | 0.0480 (5) | 0.5292 (3) | 0.6791 (2) | 0.0366 (9) | |
O41B | −0.0662 (4) | 0.5669 (3) | 0.6690 (2) | 0.0581 (10) | |
C51B | −0.1203 (7) | 0.4565 (4) | 0.8193 (3) | 0.0578 (8) | |
C52B | −0.2195 (7) | 0.5258 (4) | 0.8224 (3) | 0.0623 (9) | |
H52B | −0.2551 | 0.5527 | 0.7793 | 0.075* | |
C53B | −0.2680 (8) | 0.5568 (5) | 0.8876 (3) | 0.0690 (10) | |
H53B | −0.3355 | 0.6050 | 0.8889 | 0.083* | |
C54B | −0.2193 (8) | 0.5182 (5) | 0.9497 (4) | 0.0726 (10) | |
H54B | −0.2581 | 0.5370 | 0.9940 | 0.087* | |
C55B | −0.1136 (9) | 0.4519 (5) | 0.9486 (4) | 0.0746 (10) | |
H55B | −0.0743 | 0.4277 | 0.9921 | 0.089* | |
C56B | −0.0657 (8) | 0.4210 (5) | 0.8831 (3) | 0.0686 (9) | |
H56B | 0.0057 | 0.3746 | 0.8820 | 0.082* | |
C57B | −0.0745 (7) | 0.4206 (4) | 0.7481 (3) | 0.0537 (9) | |
H57B | −0.0618 | 0.3562 | 0.7523 | 0.064* | |
H58B | −0.1561 | 0.4318 | 0.7124 | 0.064* | |
O57B | 0.0647 (4) | 0.4588 (2) | 0.72201 (17) | 0.0406 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C10A | 0.0779 (19) | 0.0504 (17) | 0.0576 (18) | −0.0011 (17) | 0.0255 (15) | 0.0054 (15) |
C11A | 0.109 (4) | 0.066 (3) | 0.061 (3) | −0.008 (3) | 0.029 (2) | −0.004 (2) |
C12A | 0.094 (3) | 0.057 (2) | 0.067 (3) | −0.010 (2) | 0.025 (3) | 0.013 (2) |
C13A | 0.072 (2) | 0.064 (3) | 0.087 (3) | 0.000 (2) | 0.021 (2) | 0.002 (3) |
O10A | 0.0694 (16) | 0.0428 (15) | 0.0523 (15) | 0.0063 (14) | 0.0190 (13) | 0.0108 (12) |
C14A | 0.059 (2) | 0.0384 (18) | 0.0454 (19) | 0.0095 (17) | 0.0130 (16) | 0.0090 (15) |
O14A | 0.064 (2) | 0.0401 (18) | 0.054 (2) | 0.0143 (16) | 0.0202 (16) | 0.0071 (15) |
N20A | 0.0444 (15) | 0.0343 (14) | 0.0501 (16) | 0.0107 (12) | 0.0063 (12) | 0.0065 (12) |
C20A | 0.0393 (15) | 0.0345 (14) | 0.0486 (16) | 0.0062 (13) | 0.0058 (13) | 0.0024 (13) |
C21A | 0.0424 (16) | 0.0422 (16) | 0.0605 (17) | 0.0088 (14) | 0.0083 (14) | 0.0023 (15) |
C22A | 0.0504 (17) | 0.0432 (16) | 0.0661 (18) | 0.0127 (14) | 0.0107 (14) | 0.0011 (15) |
C23A | 0.0499 (17) | 0.0372 (15) | 0.0608 (17) | 0.0132 (14) | 0.0063 (15) | 0.0052 (14) |
C24A | 0.0289 (18) | 0.0271 (18) | 0.037 (2) | 0.0000 (15) | 0.0064 (15) | −0.0032 (16) |
O24A | 0.0449 (17) | 0.0277 (14) | 0.0532 (18) | −0.0100 (13) | −0.0017 (14) | 0.0008 (13) |
N30A | 0.0326 (17) | 0.0297 (17) | 0.0327 (17) | −0.0085 (14) | −0.0006 (13) | −0.0022 (13) |
C30A | 0.0258 (17) | 0.0254 (18) | 0.037 (2) | −0.0039 (14) | 0.0015 (15) | −0.0012 (15) |
C31A | 0.037 (2) | 0.029 (2) | 0.038 (2) | 0.0003 (16) | 0.0063 (17) | −0.0003 (16) |
C32A | 0.038 (2) | 0.0250 (19) | 0.045 (2) | −0.0049 (17) | 0.0077 (18) | 0.0007 (17) |
O32A | 0.057 (2) | 0.0249 (15) | 0.069 (2) | −0.0093 (15) | −0.0076 (19) | −0.0001 (15) |
C33A | 0.039 (2) | 0.031 (2) | 0.043 (2) | −0.0089 (17) | 0.0005 (18) | 0.0009 (17) |
C34A | 0.0302 (19) | 0.0262 (18) | 0.038 (2) | −0.0038 (15) | 0.0021 (16) | −0.0011 (16) |
O34A | 0.0290 (15) | 0.0468 (19) | 0.0567 (19) | 0.0025 (13) | 0.0003 (13) | −0.0149 (15) |
N40A | 0.0292 (16) | 0.0313 (17) | 0.0365 (17) | −0.0044 (14) | 0.0042 (13) | −0.0028 (14) |
C40A | 0.039 (2) | 0.027 (2) | 0.040 (2) | −0.0047 (16) | 0.0063 (17) | −0.0049 (16) |
C41A | 0.035 (2) | 0.036 (2) | 0.042 (2) | −0.0028 (18) | 0.0010 (17) | 0.0007 (18) |
O41A | 0.055 (2) | 0.0319 (17) | 0.0516 (19) | −0.0058 (15) | 0.0095 (15) | 0.0024 (14) |
C51A | 0.074 (2) | 0.0601 (18) | 0.0557 (16) | −0.0069 (16) | 0.0213 (15) | 0.0031 (15) |
C52A | 0.091 (2) | 0.070 (2) | 0.0571 (17) | −0.0026 (18) | 0.0205 (17) | 0.0009 (17) |
C53A | 0.099 (2) | 0.077 (2) | 0.0625 (18) | −0.003 (2) | 0.0242 (18) | −0.0038 (18) |
C54A | 0.092 (2) | 0.075 (2) | 0.0708 (19) | −0.0027 (19) | 0.0276 (19) | −0.0079 (19) |
C55A | 0.083 (2) | 0.072 (2) | 0.0732 (19) | −0.0008 (18) | 0.0221 (19) | −0.0056 (18) |
C56A | 0.076 (2) | 0.066 (2) | 0.0643 (18) | −0.0018 (17) | 0.0181 (17) | −0.0007 (17) |
C57A | 0.070 (2) | 0.056 (2) | 0.0527 (19) | −0.0085 (19) | 0.0224 (19) | 0.0058 (18) |
O57A | 0.069 (2) | 0.0378 (18) | 0.0463 (18) | −0.0081 (16) | 0.0245 (16) | −0.0007 (14) |
C10B | 0.085 (2) | 0.079 (2) | 0.0612 (19) | −0.0277 (19) | 0.0275 (16) | −0.0165 (16) |
C11B | 0.103 (4) | 0.103 (3) | 0.086 (3) | −0.024 (3) | 0.039 (3) | −0.038 (3) |
C12B | 0.080 (3) | 0.081 (3) | 0.077 (3) | −0.021 (3) | 0.018 (2) | −0.011 (2) |
C13B | 0.102 (4) | 0.109 (3) | 0.065 (3) | −0.022 (3) | 0.029 (3) | 0.007 (2) |
O10B | 0.0814 (19) | 0.0641 (19) | 0.0554 (16) | −0.0307 (16) | 0.0230 (14) | −0.0219 (14) |
C14B | 0.074 (2) | 0.055 (2) | 0.043 (2) | −0.0295 (19) | 0.0145 (17) | −0.0153 (17) |
O14B | 0.078 (3) | 0.0388 (18) | 0.0476 (19) | −0.0198 (18) | 0.0017 (17) | −0.0002 (15) |
N20B | 0.0562 (16) | 0.0526 (17) | 0.0394 (14) | −0.0184 (15) | 0.0039 (13) | −0.0029 (13) |
C20B | 0.0505 (18) | 0.0618 (18) | 0.0391 (16) | −0.0172 (16) | 0.0021 (14) | −0.0031 (14) |
C21B | 0.0563 (18) | 0.073 (2) | 0.0477 (17) | −0.0267 (16) | 0.0047 (14) | −0.0055 (16) |
C22B | 0.0653 (19) | 0.0660 (18) | 0.0513 (17) | −0.0303 (16) | 0.0041 (15) | −0.0003 (16) |
C23B | 0.0636 (18) | 0.0562 (18) | 0.0495 (17) | −0.0241 (16) | 0.0047 (15) | −0.0023 (15) |
C24B | 0.0315 (19) | 0.0231 (17) | 0.038 (2) | −0.0019 (15) | 0.0012 (16) | 0.0033 (15) |
O24B | 0.0337 (15) | 0.0347 (15) | 0.0453 (16) | 0.0058 (13) | 0.0017 (12) | −0.0027 (13) |
N30B | 0.0265 (15) | 0.0235 (15) | 0.0351 (17) | 0.0033 (12) | −0.0015 (13) | 0.0020 (13) |
C30B | 0.0242 (17) | 0.0197 (16) | 0.0344 (19) | −0.0013 (13) | 0.0035 (14) | 0.0007 (14) |
C31B | 0.034 (2) | 0.028 (2) | 0.044 (2) | 0.0048 (16) | 0.0122 (17) | 0.0013 (16) |
C32B | 0.0270 (18) | 0.0231 (18) | 0.053 (2) | 0.0048 (15) | 0.0087 (17) | 0.0046 (17) |
O32B | 0.0345 (15) | 0.0180 (13) | 0.0565 (19) | 0.0023 (12) | 0.0104 (13) | 0.0025 (13) |
C33B | 0.0255 (19) | 0.029 (2) | 0.057 (3) | 0.0002 (16) | −0.0024 (18) | 0.0043 (19) |
C34B | 0.0268 (17) | 0.0223 (17) | 0.037 (2) | 0.0007 (14) | 0.0054 (15) | 0.0015 (15) |
O34B | 0.0461 (16) | 0.0204 (13) | 0.0475 (17) | −0.0084 (12) | −0.0018 (13) | 0.0024 (12) |
N40B | 0.0373 (18) | 0.0231 (16) | 0.0405 (19) | −0.0050 (14) | −0.0036 (15) | 0.0052 (14) |
C40B | 0.037 (2) | 0.031 (2) | 0.040 (2) | 0.0005 (17) | −0.0014 (17) | 0.0073 (17) |
C41B | 0.045 (2) | 0.028 (2) | 0.037 (2) | −0.0003 (18) | 0.0009 (18) | 0.0014 (16) |
O41B | 0.0464 (19) | 0.061 (2) | 0.067 (2) | 0.0206 (18) | 0.0162 (17) | 0.0206 (19) |
C51B | 0.0679 (19) | 0.0459 (16) | 0.0605 (15) | 0.0011 (15) | 0.0196 (15) | 0.0092 (14) |
C52B | 0.072 (2) | 0.0528 (18) | 0.0629 (17) | 0.0062 (16) | 0.0164 (17) | 0.0040 (16) |
C53B | 0.081 (2) | 0.060 (2) | 0.0662 (18) | 0.0068 (17) | 0.0196 (17) | 0.0005 (16) |
C54B | 0.089 (2) | 0.066 (2) | 0.0638 (17) | 0.0031 (18) | 0.0237 (18) | 0.0048 (17) |
C55B | 0.094 (2) | 0.068 (2) | 0.0636 (17) | 0.0064 (18) | 0.0201 (18) | 0.0122 (18) |
C56B | 0.085 (2) | 0.0590 (19) | 0.0632 (17) | 0.0078 (17) | 0.0194 (17) | 0.0136 (16) |
C57B | 0.061 (2) | 0.0389 (19) | 0.0619 (18) | −0.0052 (18) | 0.0202 (18) | 0.0073 (17) |
O57B | 0.0419 (17) | 0.0334 (16) | 0.0468 (17) | −0.0010 (13) | 0.0067 (13) | 0.0088 (13) |
C10A—O10A | 1.475 (7) | C10B—O10B | 1.468 (8) |
C10A—C13A | 1.502 (10) | C10B—C12B | 1.497 (10) |
C10A—C11A | 1.508 (9) | C10B—C13B | 1.529 (12) |
C10A—C12A | 1.518 (9) | C10B—C11B | 1.522 (10) |
C11A—H11A | 0.9800 | C11B—H11B | 0.9800 |
C11A—H12A | 0.9800 | C11B—H12B | 0.9800 |
C11A—H13A | 0.9800 | C11B—H13B | 0.9800 |
C12A—H14A | 0.9800 | C12B—H14B | 0.9800 |
C12A—H15A | 0.9800 | C12B—H15B | 0.9800 |
C12A—H16A | 0.9800 | C12B—H16B | 0.9800 |
C13A—H17A | 0.9800 | C13B—H17B | 0.9800 |
C13A—H18A | 0.9800 | C13B—H18B | 0.9800 |
C13A—H19A | 0.9800 | C13B—H19B | 0.9800 |
O10A—C14A | 1.343 (6) | O10B—C14B | 1.337 (7) |
C14A—O14A | 1.218 (6) | C14B—O14B | 1.217 (7) |
C14A—N20A | 1.347 (6) | C14B—N20B | 1.346 (7) |
N20A—C20A | 1.454 (6) | N20B—C20B | 1.447 (7) |
N20A—C23A | 1.464 (6) | N20B—C23B | 1.475 (7) |
C20A—C24A | 1.520 (6) | C20B—C24B | 1.525 (6) |
C20A—C21A | 1.547 (6) | C20B—C21B | 1.546 (7) |
C20A—H20A | 1.0000 | C20B—H20B | 1.0000 |
C21A—C22A | 1.517 (8) | C21B—C22B | 1.511 (10) |
C21A—H21A | 0.9900 | C21B—H21B | 0.9900 |
C21A—H22A | 0.9900 | C21B—H22B | 0.9900 |
C22A—C23A | 1.521 (8) | C22B—C23B | 1.499 (8) |
C22A—H23A | 0.9900 | C22B—H23B | 0.9900 |
C22A—H24A | 0.9900 | C22B—H24B | 0.9900 |
C23A—H25A | 0.9900 | C23B—H25B | 0.9900 |
C23A—H26A | 0.9900 | C23B—H26B | 0.9900 |
C24A—O24A | 1.234 (5) | C24B—O24B | 1.226 (5) |
C24A—N30A | 1.336 (5) | C24B—N30B | 1.342 (5) |
N30A—C30A | 1.466 (5) | N30B—C30B | 1.463 (5) |
N30A—C33A | 1.460 (5) | N30B—C33B | 1.473 (5) |
C30A—C34A | 1.523 (6) | C30B—C34B | 1.529 (5) |
C30A—C31A | 1.537 (6) | C30B—C31B | 1.544 (5) |
C30A—H30A | 1.0000 | C30B—H30B | 1.0000 |
C31A—C32A | 1.518 (6) | C31B—C32B | 1.517 (6) |
C31A—H33A | 0.9900 | C31B—H33B | 0.9900 |
C31A—H34A | 0.9900 | C31B—H34B | 0.9900 |
C32A—O32A | 1.414 (5) | C32B—O32B | 1.438 (5) |
C32A—C33A | 1.534 (6) | C32B—C33B | 1.519 (6) |
C32A—H35A | 1.0000 | C32B—H35B | 1.0000 |
O32A—H32A | 0.80 (8) | O32B—H32B | 0.75 (7) |
C33A—H36A | 0.9900 | C33B—H36B | 0.9900 |
C33A—H37A | 0.9900 | C33B—H37B | 0.9900 |
C34A—O34A | 1.218 (5) | C34B—O34B | 1.236 (5) |
C34A—N40A | 1.348 (5) | C34B—N40B | 1.332 (5) |
N40A—C40A | 1.449 (5) | N40B—C40B | 1.455 (5) |
N40A—H40A | 0.8800 | N40B—H40B | 0.8800 |
C40A—C41A | 1.508 (6) | C40B—C41B | 1.521 (6) |
C40A—H41A | 0.9900 | C40B—H41B | 0.9900 |
C40A—H42A | 0.9900 | C40B—H42B | 0.9900 |
C41A—O41A | 1.192 (6) | C41B—O41B | 1.180 (6) |
C41A—O57A | 1.339 (6) | C41B—O57B | 1.345 (5) |
C51A—C52A | 1.378 (9) | C51B—C52B | 1.378 (8) |
C51A—C56A | 1.383 (10) | C51B—C56B | 1.386 (9) |
C51A—C57A | 1.499 (8) | C51B—C57B | 1.504 (8) |
C52A—C53A | 1.391 (10) | C52B—C53B | 1.386 (9) |
C52A—H52A | 0.9500 | C52B—H52B | 0.9500 |
C53A—C54A | 1.350 (11) | C53B—C54B | 1.363 (10) |
C53A—H53A | 0.9500 | C53B—H53B | 0.9500 |
C54A—C55A | 1.352 (10) | C54B—C55B | 1.380 (10) |
C54A—H54A | 0.9500 | C54B—H54B | 0.9500 |
C55A—C56A | 1.393 (9) | C55B—C56B | 1.390 (9) |
C55A—H55A | 0.9500 | C55B—H55B | 0.9500 |
C56A—H56A | 0.9500 | C56B—H56B | 0.9500 |
C57A—O57A | 1.454 (6) | C57B—O57B | 1.466 (6) |
C57A—H57A | 0.9900 | C57B—H57B | 0.9900 |
C57A—H58A | 0.9900 | C57B—H58B | 0.9900 |
O10A—C10A—C13A | 110.0 (5) | O10B—C10B—C12B | 108.8 (5) |
O10A—C10A—C11A | 109.4 (5) | O10B—C10B—C13B | 109.9 (6) |
C13A—C10A—C11A | 113.6 (6) | C12B—C10B—C13B | 113.3 (6) |
O10A—C10A—C12A | 101.4 (5) | O10B—C10B—C11B | 102.1 (5) |
C13A—C10A—C12A | 110.1 (6) | C12B—C10B—C11B | 110.4 (7) |
C11A—C10A—C12A | 111.7 (6) | C13B—C10B—C11B | 111.8 (6) |
C10A—C11A—H11A | 109.5 | C10B—C11B—H11B | 109.5 |
C10A—C11A—H12A | 109.5 | C10B—C11B—H12B | 109.5 |
H11A—C11A—H12A | 109.5 | H11B—C11B—H12B | 109.5 |
C10A—C11A—H13A | 109.5 | C10B—C11B—H13B | 109.5 |
H11A—C11A—H13A | 109.5 | H11B—C11B—H13B | 109.5 |
H12A—C11A—H13A | 109.5 | H12B—C11B—H13B | 109.5 |
C10A—C12A—H14A | 109.5 | C10B—C12B—H14B | 109.5 |
C10A—C12A—H15A | 109.5 | C10B—C12B—H15B | 109.5 |
H14A—C12A—H15A | 109.5 | H14B—C12B—H15B | 109.5 |
C10A—C12A—H16A | 109.5 | C10B—C12B—H16B | 109.5 |
H14A—C12A—H16A | 109.5 | H14B—C12B—H16B | 109.5 |
H15A—C12A—H16A | 109.5 | H15B—C12B—H16B | 109.5 |
C10A—C13A—H17A | 109.5 | C10B—C13B—H17B | 109.5 |
C10A—C13A—H18A | 109.5 | C10B—C13B—H18B | 109.5 |
H17A—C13A—H18A | 109.5 | H17B—C13B—H18B | 109.5 |
C10A—C13A—H19A | 109.5 | C10B—C13B—H19B | 109.5 |
H17A—C13A—H19A | 109.5 | H17B—C13B—H19B | 109.5 |
H18A—C13A—H19A | 109.5 | H18B—C13B—H19B | 109.5 |
C14A—O10A—C10A | 120.1 (4) | C14B—O10B—C10B | 121.5 (4) |
O14A—C14A—O10A | 126.2 (4) | O14B—C14B—O10B | 126.0 (5) |
O14A—C14A—N20A | 123.5 (5) | O14B—C14B—N20B | 124.2 (5) |
O10A—C14A—N20A | 110.3 (4) | O10B—C14B—N20B | 109.8 (5) |
C14A—N20A—C20A | 119.7 (4) | C14B—N20B—C20B | 119.9 (5) |
C14A—N20A—C23A | 126.9 (4) | C14B—N20B—C23B | 125.3 (5) |
C20A—N20A—C23A | 112.9 (4) | C20B—N20B—C23B | 113.1 (4) |
N20A—C20A—C24A | 111.3 (4) | N20B—C20B—C24B | 112.2 (4) |
N20A—C20A—C21A | 102.4 (4) | N20B—C20B—C21B | 100.5 (4) |
C24A—C20A—C21A | 109.0 (4) | C24B—C20B—C21B | 109.4 (4) |
N20A—C20A—H20A | 111.3 | N20B—C20B—H20B | 111.4 |
C24A—C20A—H20A | 111.3 | C24B—C20B—H20B | 111.4 |
C21A—C20A—H20A | 111.3 | C21B—C20B—H20B | 111.4 |
C22A—C21A—C20A | 102.7 (4) | C22B—C21B—C20B | 103.3 (5) |
C22A—C21A—H21A | 111.2 | C22B—C21B—H21B | 111.1 |
C20A—C21A—H21A | 111.2 | C20B—C21B—H21B | 111.1 |
C22A—C21A—H22A | 111.2 | C22B—C21B—H22B | 111.1 |
C20A—C21A—H22A | 111.2 | C20B—C21B—H22B | 111.1 |
H21A—C21A—H22A | 109.1 | H21B—C21B—H22B | 109.1 |
C21A—C22A—C23A | 103.8 (4) | C23B—C22B—C21B | 103.5 (5) |
C21A—C22A—H23A | 111.0 | C23B—C22B—H23B | 111.1 |
C23A—C22A—H23A | 111.0 | C21B—C22B—H23B | 111.1 |
C21A—C22A—H24A | 111.0 | C23B—C22B—H24B | 111.1 |
C23A—C22A—H24A | 111.0 | C21B—C22B—H24B | 111.1 |
H23A—C22A—H24A | 109.0 | H23B—C22B—H24B | 109.0 |
N20A—C23A—C22A | 103.3 (4) | N20B—C23B—C22B | 103.5 (5) |
N20A—C23A—H25A | 111.1 | N20B—C23B—H25B | 111.1 |
C22A—C23A—H25A | 111.1 | C22B—C23B—H25B | 111.1 |
N20A—C23A—H26A | 111.1 | N20B—C23B—H26B | 111.1 |
C22A—C23A—H26A | 111.1 | C22B—C23B—H26B | 111.1 |
H25A—C23A—H26A | 109.1 | H25B—C23B—H26B | 109.0 |
O24A—C24A—N30A | 121.5 (4) | O24B—C24B—N30B | 121.9 (4) |
O24A—C24A—C20A | 121.6 (4) | O24B—C24B—C20B | 121.2 (4) |
N30A—C24A—C20A | 116.8 (4) | N30B—C24B—C20B | 116.8 (4) |
C24A—N30A—C30A | 120.5 (3) | C24B—N30B—C30B | 120.3 (3) |
C24A—N30A—C33A | 126.8 (3) | C24B—N30B—C33B | 127.5 (3) |
C30A—N30A—C33A | 112.4 (3) | C30B—N30B—C33B | 112.1 (3) |
N30A—C30A—C34A | 110.3 (3) | N30B—C30B—C34B | 112.0 (3) |
N30A—C30A—C31A | 103.2 (3) | N30B—C30B—C31B | 103.2 (3) |
C34A—C30A—C31A | 109.2 (3) | C34B—C30B—C31B | 112.0 (3) |
N30A—C30A—H30A | 111.3 | N30B—C30B—H30B | 109.8 |
C34A—C30A—H30A | 111.3 | C34B—C30B—H30B | 109.8 |
C31A—C30A—H30A | 111.3 | C31B—C30B—H30B | 109.8 |
C32A—C31A—C30A | 103.7 (3) | C32B—C31B—C30B | 103.0 (3) |
C32A—C31A—H33A | 111.0 | C32B—C31B—H33B | 111.2 |
C30A—C31A—H33A | 111.0 | C30B—C31B—H33B | 111.2 |
C32A—C31A—H34A | 111.0 | C32B—C31B—H34B | 111.2 |
C30A—C31A—H34A | 111.0 | C30B—C31B—H34B | 111.2 |
H33A—C31A—H34A | 109.0 | H33B—C31B—H34B | 109.1 |
O32A—C32A—C31A | 110.2 (4) | O32B—C32B—C33B | 107.4 (4) |
O32A—C32A—C33A | 111.9 (4) | O32B—C32B—C31B | 110.9 (3) |
C31A—C32A—C33A | 104.4 (3) | C33B—C32B—C31B | 102.9 (3) |
O32A—C32A—H35A | 110.0 | O32B—C32B—H35B | 111.7 |
C31A—C32A—H35A | 110.0 | C33B—C32B—H35B | 111.7 |
C33A—C32A—H35A | 110.0 | C31B—C32B—H35B | 111.7 |
C32A—O32A—H32A | 106 (6) | C32B—O32B—H32B | 106 (5) |
N30A—C33A—C32A | 104.3 (3) | N30B—C33B—C32B | 101.2 (3) |
N30A—C33A—H36A | 110.9 | N30B—C33B—H36B | 111.5 |
C32A—C33A—H36A | 110.9 | C32B—C33B—H36B | 111.5 |
N30A—C33A—H37A | 110.9 | N30B—C33B—H37B | 111.5 |
C32A—C33A—H37A | 110.9 | C32B—C33B—H37B | 111.5 |
H36A—C33A—H37A | 108.9 | H36B—C33B—H37B | 109.3 |
O34A—C34A—N40A | 123.3 (4) | O34B—C34B—N40B | 123.8 (4) |
O34A—C34A—C30A | 121.9 (4) | O34B—C34B—C30B | 121.9 (3) |
N40A—C34A—C30A | 114.7 (3) | N40B—C34B—C30B | 114.3 (3) |
C34A—N40A—C40A | 119.3 (3) | C34B—N40B—C40B | 121.6 (3) |
C34A—N40A—H40A | 120.4 | C34B—N40B—H40B | 119.2 |
C40A—N40A—H40A | 120.4 | C40B—N40B—H40B | 119.2 |
N40A—C40A—C41A | 112.4 (3) | N40B—C40B—C41B | 112.2 (4) |
N40A—C40A—H41A | 109.1 | N40B—C40B—H41B | 109.2 |
C41A—C40A—H41A | 109.1 | C41B—C40B—H41B | 109.2 |
N40A—C40A—H42A | 109.1 | N40B—C40B—H42B | 109.2 |
C41A—C40A—H42A | 109.1 | C41B—C40B—H42B | 109.2 |
H41A—C40A—H42A | 107.9 | H41B—C40B—H42B | 107.9 |
O41A—C41A—O57A | 124.2 (4) | O41B—C41B—O57B | 124.3 (4) |
O41A—C41A—C40A | 126.8 (4) | O41B—C41B—C40B | 125.5 (4) |
O57A—C41A—C40A | 109.1 (4) | O57B—C41B—C40B | 110.2 (4) |
C52A—C51A—C56A | 118.7 (6) | C52B—C51B—C56B | 118.2 (6) |
C52A—C51A—C57A | 120.7 (6) | C52B—C51B—C57B | 120.3 (5) |
C56A—C51A—C57A | 120.6 (6) | C56B—C51B—C57B | 121.5 (6) |
C51A—C52A—C53A | 119.2 (7) | C51B—C52B—C53B | 120.9 (6) |
C51A—C52A—H52A | 120.4 | C51B—C52B—H52B | 119.6 |
C53A—C52A—H52A | 120.4 | C53B—C52B—H52B | 119.6 |
C54A—C53A—C52A | 121.2 (7) | C54B—C53B—C52B | 120.2 (6) |
C54A—C53A—H53A | 119.4 | C54B—C53B—H53B | 119.9 |
C52A—C53A—H53A | 119.4 | C52B—C53B—H53B | 119.9 |
C55A—C54A—C53A | 120.7 (7) | C53B—C54B—C55B | 120.3 (6) |
C55A—C54A—H54A | 119.7 | C53B—C54B—H54B | 119.9 |
C53A—C54A—H54A | 119.7 | C55B—C54B—H54B | 119.9 |
C54A—C55A—C56A | 119.2 (8) | C56B—C55B—C54B | 119.1 (7) |
C54A—C55A—H55A | 120.4 | C56B—C55B—H55B | 120.5 |
C56A—C55A—H55A | 120.4 | C54B—C55B—H55B | 120.5 |
C51A—C56A—C55A | 121.0 (6) | C55B—C56B—C51B | 121.1 (6) |
C51A—C56A—H56A | 119.5 | C55B—C56B—H56B | 119.4 |
C55A—C56A—H56A | 119.5 | C51B—C56B—H56B | 119.4 |
O57A—C57A—C51A | 108.0 (5) | O57B—C57B—C51B | 113.8 (5) |
O57A—C57A—H57A | 110.1 | O57B—C57B—H57B | 108.8 |
C51A—C57A—H57A | 110.1 | C51B—C57B—H57B | 108.8 |
O57A—C57A—H58A | 110.1 | O57B—C57B—H58B | 108.8 |
C51A—C57A—H58A | 110.1 | C51B—C57B—H58B | 108.8 |
H57A—C57A—H58A | 108.4 | H57B—C57B—H58B | 107.7 |
C41A—O57A—C57A | 116.0 (4) | C41B—O57B—C57B | 115.6 (4) |
C13A—C10A—O10A—C14A | 62.8 (7) | C12B—C10B—O10B—C14B | 63.8 (8) |
C11A—C10A—O10A—C14A | −62.6 (7) | C13B—C10B—O10B—C14B | −60.8 (8) |
C12A—C10A—O10A—C14A | 179.3 (5) | C11B—C10B—O10B—C14B | −179.5 (6) |
C10A—O10A—C14A—O14A | 0.6 (9) | C10B—O10B—C14B—O14B | 13.6 (10) |
C10A—O10A—C14A—N20A | 179.1 (5) | C10B—O10B—C14B—N20B | −167.6 (6) |
O14A—C14A—N20A—C20A | −7.8 (8) | O14B—C14B—N20B—C20B | −5.5 (9) |
O10A—C14A—N20A—C20A | 173.6 (4) | O10B—C14B—N20B—C20B | 175.7 (5) |
O14A—C14A—N20A—C23A | −179.1 (5) | O14B—C14B—N20B—C23B | −170.0 (6) |
O10A—C14A—N20A—C23A | 2.4 (8) | O10B—C14B—N20B—C23B | 11.2 (8) |
C14A—N20A—C20A—C24A | −71.1 (6) | C14B—N20B—C20B—C24B | −69.9 (7) |
C23A—N20A—C20A—C24A | 101.3 (5) | C23B—N20B—C20B—C24B | 96.4 (5) |
C14A—N20A—C20A—C21A | 172.6 (5) | C14B—N20B—C20B—C21B | 174.0 (5) |
C23A—N20A—C20A—C21A | −15.0 (5) | C23B—N20B—C20B—C21B | −19.7 (6) |
N20A—C20A—C21A—C22A | 32.7 (5) | N20B—C20B—C21B—C22B | 35.9 (5) |
C24A—C20A—C21A—C22A | −85.3 (5) | C24B—C20B—C21B—C22B | −82.3 (5) |
C20A—C21A—C22A—C23A | −38.8 (5) | C20B—C21B—C22B—C23B | −39.9 (5) |
C14A—N20A—C23A—C22A | 162.9 (5) | C14B—N20B—C23B—C22B | 161.0 (5) |
C20A—N20A—C23A—C22A | −8.8 (6) | C20B—N20B—C23B—C22B | −4.4 (6) |
C21A—C22A—C23A—N20A | 29.6 (6) | C21B—C22B—C23B—N20B | 27.4 (6) |
N20A—C20A—C24A—O24A | −19.4 (6) | N20B—C20B—C24B—O24B | −9.4 (6) |
C21A—C20A—C24A—O24A | 92.8 (5) | C21B—C20B—C24B—O24B | 101.2 (5) |
N20A—C20A—C24A—N30A | 164.0 (4) | N20B—C20B—C24B—N30B | 174.2 (4) |
C21A—C20A—C24A—N30A | −83.8 (5) | C21B—C20B—C24B—N30B | −75.2 (6) |
O24A—C24A—N30A—C30A | −8.0 (6) | O24B—C24B—N30B—C30B | −8.4 (6) |
C20A—C24A—N30A—C30A | 168.6 (3) | C20B—C24B—N30B—C30B | 168.0 (4) |
O24A—C24A—N30A—C33A | 179.1 (4) | O24B—C24B—N30B—C33B | 166.2 (4) |
C20A—C24A—N30A—C33A | −4.2 (6) | C20B—C24B—N30B—C33B | −17.4 (6) |
C24A—N30A—C30A—C34A | −73.8 (4) | C24B—N30B—C30B—C34B | −63.1 (4) |
C33A—N30A—C30A—C34A | 100.0 (4) | C33B—N30B—C30B—C34B | 121.6 (3) |
C24A—N30A—C30A—C31A | 169.6 (3) | C24B—N30B—C30B—C31B | 176.2 (3) |
C33A—N30A—C30A—C31A | −16.6 (4) | C33B—N30B—C30B—C31B | 0.8 (4) |
N30A—C30A—C31A—C32A | 31.2 (4) | N30B—C30B—C31B—C32B | −25.5 (4) |
C34A—C30A—C31A—C32A | −86.2 (4) | C34B—C30B—C31B—C32B | −146.3 (3) |
C30A—C31A—C32A—O32A | −154.9 (4) | C30B—C31B—C32B—O32B | −74.0 (4) |
C30A—C31A—C32A—C33A | −34.5 (4) | C30B—C31B—C32B—C33B | 40.6 (4) |
C24A—N30A—C33A—C32A | 168.7 (4) | C24B—N30B—C33B—C32B | −151.0 (4) |
C30A—N30A—C33A—C32A | −4.7 (5) | C30B—N30B—C33B—C32B | 24.0 (4) |
O32A—C32A—C33A—N30A | 143.7 (4) | O32B—C32B—C33B—N30B | 77.9 (4) |
C31A—C32A—C33A—N30A | 24.4 (4) | C31B—C32B—C33B—N30B | −39.2 (4) |
N30A—C30A—C34A—O34A | −35.4 (5) | N30B—C30B—C34B—O34B | −10.3 (5) |
C31A—C30A—C34A—O34A | 77.3 (5) | C31B—C30B—C34B—O34B | 105.1 (4) |
N30A—C30A—C34A—N40A | 148.8 (3) | N30B—C30B—C34B—N40B | 171.7 (3) |
C31A—C30A—C34A—N40A | −98.4 (4) | C31B—C30B—C34B—N40B | −72.9 (4) |
O34A—C34A—N40A—C40A | −7.6 (6) | O34B—C34B—N40B—C40B | −3.3 (6) |
C30A—C34A—N40A—C40A | 168.0 (3) | C30B—C34B—N40B—C40B | 174.6 (3) |
C34A—N40A—C40A—C41A | −70.9 (5) | C34B—N40B—C40B—C41B | −66.2 (5) |
N40A—C40A—C41A—O41A | −3.5 (7) | N40B—C40B—C41B—O41B | 1.5 (7) |
N40A—C40A—C41A—O57A | 176.5 (4) | N40B—C40B—C41B—O57B | 179.2 (3) |
C56A—C51A—C52A—C53A | −3.3 (10) | C56B—C51B—C52B—C53B | −2.5 (10) |
C57A—C51A—C52A—C53A | 175.5 (6) | C57B—C51B—C52B—C53B | 176.9 (6) |
C51A—C52A—C53A—C54A | 2.1 (11) | C51B—C52B—C53B—C54B | −0.8 (11) |
C52A—C53A—C54A—C55A | 0.1 (12) | C52B—C53B—C54B—C55B | 4.3 (11) |
C53A—C54A—C55A—C56A | −0.9 (12) | C53B—C54B—C55B—C56B | −4.4 (11) |
C52A—C51A—C56A—C55A | 2.5 (10) | C54B—C55B—C56B—C51B | 1.1 (11) |
C57A—C51A—C56A—C55A | −176.3 (6) | C52B—C51B—C56B—C55B | 2.3 (10) |
C54A—C55A—C56A—C51A | −0.4 (11) | C57B—C51B—C56B—C55B | −177.1 (6) |
C52A—C51A—C57A—O57A | 134.1 (6) | C52B—C51B—C57B—O57B | 94.3 (7) |
C56A—C51A—C57A—O57A | −47.2 (8) | C56B—C51B—C57B—O57B | −86.3 (7) |
O41A—C41A—O57A—C57A | −3.3 (7) | O41B—C41B—O57B—C57B | 9.6 (7) |
C40A—C41A—O57A—C57A | 176.7 (4) | C40B—C41B—O57B—C57B | −168.2 (4) |
C51A—C57A—O57A—C41A | 177.1 (5) | C51B—C57B—O57B—C41B | −92.5 (5) |
C22H31N3O7 | Z = 2 |
Mr = 449.50 | F(000) = 480 |
TriclinicP1 | Dx = 1.272 Mg m−3 |
a = 5.8816 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.6294 (6) Å | Cell parameters from 8664 reflections |
c = 19.707 (1) Å | θ = 2.5–28.3° |
α = 75.240 (1)° | µ = 0.10 mm−1 |
β = 82.560 (1)° | T = 200 K |
γ = 81.780 (1)° | Plate, colourless |
V = 1173.6 (1) Å3 | 0.45 × 0.35 × 0.20 mm |
Bruker AXS, SMART APEX CCD area detector diffractometer | 5142 independent reflections |
Radiation source: MacScience, M18XCE rotating anode | 5049 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
Detector resolution: 8.366 pixels mm-1 | θmax = 27.1°, θmin = 2.0° |
ω–scan | h = −7→7 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −13→13 |
Tmin = 0.927, Tmax = 0.981 | l = −25→25 |
13595 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0684P)2 + 0.1501P] where P = (Fo2 + 2Fc2)/3 |
5142 reflections | (Δ/σ)max = 0.002 |
593 parameters | Δρmax = 0.43 e Å−3 |
245 restraints | Δρmin = −0.16 e Å−3 |
C22H31N3O7 | γ = 81.780 (1)° |
Mr = 449.50 | V = 1173.6 (1) Å3 |
TriclinicP1 | Z = 2 |
a = 5.8816 (3) Å | Mo Kα radiation |
b = 10.6294 (6) Å | µ = 0.10 mm−1 |
c = 19.707 (1) Å | T = 200 K |
α = 75.240 (1)° | 0.45 × 0.35 × 0.20 mm |
β = 82.560 (1)° |
Bruker AXS, SMART APEX CCD area detector diffractometer | 5142 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 5049 reflections with I > 2σ(I) |
Tmin = 0.927, Tmax = 0.981 | Rint = 0.015 |
13595 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 245 restraints |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.43 e Å−3 |
5142 reflections | Δρmin = −0.16 e Å−3 |
593 parameters |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C10A | 0.7486 (10) | 1.0329 (6) | −0.2855 (3) | 0.0351 (11) | |
C11A | 0.7676 (13) | 1.1789 (7) | −0.3027 (4) | 0.0500 (15) | |
H11A | 0.6924 | 1.2151 | −0.2634 | 0.075* | |
H12A | 0.6920 | 1.2223 | −0.3454 | 0.075* | |
H13A | 0.9308 | 1.1934 | −0.3105 | 0.075* | |
C12A | 0.8714 (14) | 0.9732 (8) | −0.3446 (3) | 0.0513 (16) | |
H14A | 1.0351 | 0.9863 | −0.3507 | 0.077* | |
H15A | 0.8015 | 1.0155 | −0.3885 | 0.077* | |
H16A | 0.8566 | 0.8792 | −0.3327 | 0.077* | |
C13A | 0.4979 (11) | 1.0058 (7) | −0.2696 (4) | 0.0455 (14) | |
H17A | 0.4902 | 0.9113 | −0.2599 | 0.068* | |
H18A | 0.4132 | 1.0506 | −0.3103 | 0.068* | |
H19A | 0.4286 | 1.0381 | −0.2284 | 0.068* | |
O10A | 0.8736 (7) | 0.9848 (4) | −0.2219 (2) | 0.0344 (8) | |
C14A | 0.8961 (9) | 0.8555 (5) | −0.1890 (3) | 0.0305 (10) | |
O14A | 0.8158 (8) | 0.7710 (4) | −0.2062 (2) | 0.0415 (9) | |
N20A | 1.0202 (8) | 0.8364 (4) | −0.1335 (2) | 0.0331 (9) | |
H20A | 1.0618 | 0.9042 | −0.1222 | 0.040* | |
C20A | 1.0857 (9) | 0.7053 (5) | −0.0921 (3) | 0.0298 (10) | |
H21A | 1.0728 | 0.6412 | −0.1204 | 0.036* | |
C21A | 1.3359 (10) | 0.6911 (7) | −0.0747 (3) | 0.0414 (13) | |
H22A | 1.4389 | 0.7051 | −0.1186 | 0.062* | |
H23A | 1.3763 | 0.6030 | −0.0456 | 0.062* | |
H24A | 1.3525 | 0.7563 | −0.0489 | 0.062* | |
C22A | 0.9254 (8) | 0.6736 (5) | −0.0233 (3) | 0.0265 (9) | |
O22A | 0.8313 (7) | 0.7592 (4) | 0.0058 (2) | 0.0358 (8) | |
N30A | 0.9017 (8) | 0.5475 (4) | 0.0056 (3) | 0.0333 (10) | |
C30A | 0.7548 (11) | 0.5098 (6) | 0.0715 (3) | 0.0399 (13) | |
H30A | 0.5930 | 0.5523 | 0.0662 | 0.048* | |
C31A | 0.7655 (19) | 0.3598 (7) | 0.0834 (4) | 0.067 (2) | |
H33A | 0.8870 | 0.3141 | 0.1144 | 0.080* | |
H34A | 0.6155 | 0.3292 | 0.1051 | 0.080* | |
C32A | 0.8216 (12) | 0.3357 (5) | 0.0109 (4) | 0.0490 (16) | |
H35A | 0.8942 | 0.2440 | 0.0128 | 0.059* | |
O32A | 0.6261 (9) | 0.3667 (5) | −0.0275 (3) | 0.0471 (11) | |
H32A | 0.550 (13) | 0.313 (8) | −0.009 (4) | 0.034 (18)* | |
C33A | 0.9885 (12) | 0.4350 (6) | −0.0252 (6) | 0.061 (2) | |
H36A | 1.1487 | 0.4010 | −0.0143 | 0.073* | |
H37A | 0.9830 | 0.4590 | −0.0769 | 0.073* | |
C34A | 0.8474 (10) | 0.5392 (5) | 0.1340 (3) | 0.0361 (11) | |
O34A | 1.0538 (8) | 0.5205 (4) | 0.1411 (3) | 0.0444 (10) | |
N40A | 0.6882 (10) | 0.5768 (6) | 0.1821 (3) | 0.0469 (12) | |
H40A | 0.5464 | 0.6021 | 0.1705 | 0.056* | |
C40A | 0.7364 (13) | 0.5781 (6) | 0.2518 (4) | 0.0470 (14) | |
H41A | 0.6064 | 0.6295 | 0.2734 | 0.056* | |
H42A | 0.8768 | 0.6218 | 0.2481 | 0.056* | |
C41A | 0.7718 (10) | 0.4418 (6) | 0.2987 (3) | 0.0377 (12) | |
O41A | 0.7138 (11) | 0.3458 (5) | 0.2900 (3) | 0.0557 (12) | |
O50A | 0.8804 (10) | 0.4459 (6) | 0.3530 (3) | 0.0580 (13) | |
C50A | 0.9054 (16) | 0.3260 (11) | 0.4082 (4) | 0.0713 (15) | |
H50A | 1.0460 | 0.3226 | 0.4316 | 0.086* | |
H51A | 0.9223 | 0.2494 | 0.3873 | 0.086* | |
C51A | 0.6981 (14) | 0.3206 (8) | 0.4614 (3) | 0.0522 (11) | |
C52A | 0.564 (2) | 0.2194 (10) | 0.4749 (5) | 0.0719 (12) | |
H52A | 0.6011 | 0.1513 | 0.4507 | 0.086* | |
C53A | 0.371 (2) | 0.2183 (14) | 0.5250 (6) | 0.0927 (14) | |
H53A | 0.2771 | 0.1490 | 0.5352 | 0.111* | |
C54A | 0.319 (2) | 0.3179 (16) | 0.5591 (6) | 0.0983 (15) | |
H54A | 0.1864 | 0.3181 | 0.5921 | 0.118* | |
C55A | 0.454 (3) | 0.4153 (14) | 0.5466 (6) | 0.0981 (15) | |
H55A | 0.4179 | 0.4827 | 0.5713 | 0.118* | |
C56A | 0.644 (2) | 0.4166 (10) | 0.4982 (5) | 0.0754 (13) | |
H56A | 0.7402 | 0.4848 | 0.4899 | 0.090* | |
C10B | 0.9358 (11) | −0.1443 (7) | 0.4336 (3) | 0.0456 (15) | |
C11B | 1.0680 (13) | −0.2573 (8) | 0.4061 (4) | 0.0570 (18) | |
H11B | 0.9660 | −0.2924 | 0.3817 | 0.085* | |
H12B | 1.1244 | −0.3262 | 0.4456 | 0.085* | |
H13B | 1.1993 | −0.2263 | 0.3731 | 0.085* | |
C12B | 0.7312 (13) | −0.1857 (10) | 0.4861 (4) | 0.061 (2) | |
H14B | 0.6437 | −0.1085 | 0.4993 | 0.091* | |
H15B | 0.7867 | −0.2477 | 0.5282 | 0.091* | |
H16B | 0.6311 | −0.2276 | 0.4646 | 0.091* | |
C13B | 1.0949 (13) | −0.0788 (10) | 0.4659 (4) | 0.059 (2) | |
H17B | 1.2189 | −0.0464 | 0.4302 | 0.089* | |
H18B | 1.1618 | −0.1426 | 0.5056 | 0.089* | |
H19B | 1.0061 | −0.0054 | 0.4826 | 0.089* | |
O10B | 0.8562 (7) | −0.0356 (4) | 0.3756 (2) | 0.0386 (9) | |
C14B | 0.6877 (9) | −0.0499 (6) | 0.3378 (3) | 0.0322 (10) | |
O14B | 0.6252 (8) | −0.1529 (4) | 0.3372 (3) | 0.0457 (10) | |
N20B | 0.5982 (8) | 0.0677 (5) | 0.3017 (2) | 0.0336 (10) | |
H20B | 0.6527 | 0.1394 | 0.3037 | 0.040* | |
C20B | 0.4094 (9) | 0.0750 (6) | 0.2591 (3) | 0.0318 (10) | |
H21B | 0.2960 | 0.0149 | 0.2868 | 0.038* | |
C21B | 0.2877 (12) | 0.2139 (7) | 0.2415 (4) | 0.0477 (15) | |
H22B | 0.2305 | 0.2408 | 0.2852 | 0.072* | |
H23B | 0.1577 | 0.2170 | 0.2144 | 0.072* | |
H24B | 0.3965 | 0.2734 | 0.2135 | 0.072* | |
C22B | 0.4976 (8) | 0.0335 (5) | 0.1902 (3) | 0.0266 (9) | |
O22B | 0.6796 (6) | 0.0650 (4) | 0.1569 (2) | 0.0334 (8) | |
N30B | 0.3575 (7) | −0.0322 (4) | 0.1672 (2) | 0.0292 (9) | |
C30B | 0.4132 (9) | −0.0670 (5) | 0.0996 (3) | 0.0285 (10) | |
H30B | 0.5459 | −0.1376 | 0.1019 | 0.034* | |
C31B | 0.1897 (11) | −0.1180 (6) | 0.0896 (3) | 0.0413 (13) | |
H33B | 0.0783 | −0.0455 | 0.0668 | 0.050* | |
H34B | 0.2232 | −0.1837 | 0.0608 | 0.050* | |
C32B | 0.0987 (10) | −0.1796 (6) | 0.1646 (3) | 0.0372 (12) | |
H35B | −0.0706 | −0.1861 | 0.1681 | 0.045* | |
O32B | 0.2234 (8) | −0.3050 (5) | 0.1909 (3) | 0.0459 (10) | |
H32B | 0.16 (2) | −0.359 (12) | 0.178 (6) | 0.08 (3)* | |
C33B | 0.1479 (10) | −0.0866 (6) | 0.2063 (3) | 0.0371 (12) | |
H36B | 0.0179 | −0.0165 | 0.2075 | 0.045* | |
H37B | 0.1760 | −0.1337 | 0.2552 | 0.045* | |
C34B | 0.4595 (8) | 0.0488 (5) | 0.0382 (2) | 0.0262 (9) | |
O34B | 0.3609 (7) | 0.1598 (4) | 0.0343 (2) | 0.0324 (8) | |
N40B | 0.5990 (8) | 0.0148 (4) | −0.0155 (2) | 0.0324 (9) | |
H40B | 0.6822 | −0.0623 | −0.0090 | 0.039* | |
C40B | 0.6111 (10) | 0.1054 (5) | −0.0836 (3) | 0.0338 (11) | |
H41B | 0.7199 | 0.0654 | −0.1170 | 0.041* | |
H42B | 0.6712 | 0.1855 | −0.0799 | 0.041* | |
C41B | 0.3765 (10) | 0.1421 (5) | −0.1118 (3) | 0.0330 (11) | |
O41B | 0.2205 (8) | 0.0759 (4) | −0.1001 (2) | 0.0450 (10) | |
O50B | 0.3724 (8) | 0.2614 (4) | −0.1555 (2) | 0.0419 (10) | |
C50B | 0.1686 (12) | 0.3123 (6) | −0.1912 (4) | 0.0444 (11) | |
H50B | 0.0336 | 0.3237 | −0.1568 | 0.053* | |
H51B | 0.1365 | 0.2518 | −0.2187 | 0.053* | |
C51B | 0.2166 (12) | 0.4429 (6) | −0.2397 (3) | 0.0429 (9) | |
C52B | 0.0757 (15) | 0.4990 (7) | −0.2936 (4) | 0.0540 (10) | |
H52B | −0.0486 | 0.4559 | −0.2994 | 0.065* | |
C53B | 0.1186 (19) | 0.6198 (9) | −0.3392 (5) | 0.0694 (12) | |
H53B | 0.0230 | 0.6583 | −0.3762 | 0.083* | |
C54B | 0.2972 (17) | 0.6829 (8) | −0.3310 (5) | 0.0659 (12) | |
H54B | 0.3261 | 0.7640 | −0.3627 | 0.079* | |
C55B | 0.4339 (16) | 0.6297 (8) | −0.2774 (6) | 0.0653 (12) | |
H55B | 0.5564 | 0.6742 | −0.2715 | 0.078* | |
C56B | 0.3929 (14) | 0.5100 (7) | −0.2313 (5) | 0.0559 (11) | |
H56B | 0.4867 | 0.4738 | −0.1937 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C10A | 0.038 (3) | 0.044 (3) | 0.021 (2) | −0.002 (2) | −0.008 (2) | −0.004 (2) |
C11A | 0.060 (4) | 0.045 (3) | 0.038 (3) | −0.005 (3) | −0.015 (3) | 0.006 (3) |
C12A | 0.058 (4) | 0.068 (4) | 0.026 (3) | −0.001 (3) | −0.002 (3) | −0.013 (3) |
C13A | 0.038 (3) | 0.057 (4) | 0.042 (3) | −0.002 (3) | −0.010 (2) | −0.012 (3) |
O10A | 0.043 (2) | 0.0359 (19) | 0.0240 (17) | −0.0069 (16) | −0.0094 (15) | −0.0017 (14) |
C14A | 0.031 (2) | 0.037 (3) | 0.023 (2) | −0.007 (2) | 0.0001 (18) | −0.0063 (19) |
O14A | 0.049 (2) | 0.042 (2) | 0.038 (2) | −0.0104 (18) | −0.0124 (18) | −0.0092 (17) |
N20A | 0.043 (2) | 0.031 (2) | 0.026 (2) | −0.0110 (18) | −0.0080 (18) | −0.0012 (17) |
C20A | 0.033 (2) | 0.030 (2) | 0.025 (2) | −0.0030 (19) | −0.0034 (18) | −0.0044 (18) |
C21A | 0.030 (3) | 0.051 (3) | 0.039 (3) | −0.004 (2) | −0.001 (2) | −0.003 (3) |
C22A | 0.027 (2) | 0.025 (2) | 0.026 (2) | −0.0025 (18) | −0.0049 (17) | −0.0031 (17) |
O22A | 0.046 (2) | 0.0253 (17) | 0.0330 (19) | −0.0012 (15) | 0.0028 (16) | −0.0063 (14) |
N30A | 0.034 (2) | 0.024 (2) | 0.039 (2) | −0.0036 (17) | −0.0012 (18) | −0.0034 (17) |
C30A | 0.041 (3) | 0.038 (3) | 0.036 (3) | −0.013 (2) | −0.007 (2) | 0.009 (2) |
C31A | 0.109 (7) | 0.036 (3) | 0.057 (4) | −0.036 (4) | −0.035 (4) | 0.013 (3) |
C32A | 0.048 (3) | 0.021 (2) | 0.076 (5) | −0.005 (2) | −0.016 (3) | −0.002 (3) |
O32A | 0.055 (3) | 0.032 (2) | 0.055 (3) | −0.009 (2) | −0.015 (2) | −0.0050 (19) |
C33A | 0.043 (3) | 0.029 (3) | 0.112 (7) | −0.005 (3) | 0.012 (4) | −0.027 (4) |
C34A | 0.040 (3) | 0.024 (2) | 0.037 (3) | −0.003 (2) | −0.004 (2) | 0.004 (2) |
O34A | 0.042 (2) | 0.041 (2) | 0.053 (3) | −0.0001 (18) | −0.0114 (19) | −0.0154 (19) |
N40A | 0.043 (3) | 0.049 (3) | 0.038 (3) | 0.001 (2) | −0.003 (2) | 0.006 (2) |
C40A | 0.057 (4) | 0.036 (3) | 0.042 (3) | −0.008 (3) | 0.009 (3) | −0.004 (2) |
C41A | 0.036 (3) | 0.041 (3) | 0.033 (3) | −0.006 (2) | 0.002 (2) | −0.005 (2) |
O41A | 0.078 (4) | 0.037 (2) | 0.052 (3) | −0.012 (2) | −0.014 (2) | −0.003 (2) |
O50A | 0.063 (3) | 0.077 (4) | 0.037 (2) | −0.023 (3) | −0.006 (2) | −0.010 (2) |
C50A | 0.062 (3) | 0.102 (3) | 0.037 (2) | 0.010 (3) | −0.010 (2) | −0.001 (2) |
C51A | 0.061 (2) | 0.057 (2) | 0.0298 (18) | 0.0057 (19) | −0.0099 (17) | 0.0009 (17) |
C52A | 0.096 (3) | 0.069 (3) | 0.050 (2) | −0.010 (2) | −0.029 (2) | −0.001 (2) |
C53A | 0.084 (3) | 0.120 (3) | 0.062 (2) | −0.040 (2) | −0.028 (2) | 0.026 (2) |
C54A | 0.070 (3) | 0.143 (3) | 0.051 (2) | 0.010 (2) | 0.002 (2) | 0.016 (2) |
C55A | 0.119 (3) | 0.097 (3) | 0.055 (2) | 0.026 (2) | 0.017 (2) | −0.009 (2) |
C56A | 0.104 (3) | 0.063 (3) | 0.051 (2) | −0.003 (2) | 0.006 (2) | −0.0073 (19) |
C10B | 0.037 (3) | 0.063 (4) | 0.030 (3) | −0.003 (3) | −0.011 (2) | 0.005 (3) |
C11B | 0.050 (4) | 0.056 (4) | 0.051 (4) | 0.005 (3) | −0.009 (3) | 0.006 (3) |
C12B | 0.043 (3) | 0.090 (6) | 0.035 (3) | −0.005 (4) | −0.009 (3) | 0.012 (3) |
C13B | 0.044 (3) | 0.097 (6) | 0.037 (3) | −0.007 (4) | −0.015 (3) | −0.011 (4) |
O10B | 0.039 (2) | 0.045 (2) | 0.0317 (19) | −0.0067 (17) | −0.0137 (16) | −0.0032 (16) |
C14B | 0.032 (2) | 0.039 (3) | 0.025 (2) | −0.006 (2) | −0.0047 (19) | −0.006 (2) |
O14B | 0.050 (2) | 0.037 (2) | 0.051 (3) | −0.0091 (18) | −0.017 (2) | −0.0017 (18) |
N20B | 0.041 (2) | 0.034 (2) | 0.029 (2) | −0.0075 (19) | −0.0117 (19) | −0.0066 (17) |
C20B | 0.032 (2) | 0.039 (3) | 0.024 (2) | −0.004 (2) | −0.0047 (19) | −0.006 (2) |
C21B | 0.048 (3) | 0.052 (4) | 0.042 (3) | 0.014 (3) | −0.011 (3) | −0.017 (3) |
C22B | 0.026 (2) | 0.027 (2) | 0.025 (2) | −0.0020 (18) | −0.0064 (17) | −0.0021 (18) |
O22B | 0.0306 (18) | 0.038 (2) | 0.0324 (19) | −0.0112 (15) | −0.0005 (14) | −0.0078 (15) |
N30B | 0.029 (2) | 0.037 (2) | 0.0212 (19) | −0.0083 (17) | −0.0026 (16) | −0.0033 (16) |
C30B | 0.035 (2) | 0.027 (2) | 0.023 (2) | −0.0058 (18) | −0.0052 (18) | −0.0041 (18) |
C31B | 0.048 (3) | 0.045 (3) | 0.036 (3) | −0.021 (3) | −0.014 (2) | −0.005 (2) |
C32B | 0.032 (2) | 0.040 (3) | 0.039 (3) | −0.013 (2) | −0.010 (2) | −0.002 (2) |
O32B | 0.040 (2) | 0.041 (2) | 0.056 (3) | −0.0140 (18) | −0.014 (2) | 0.000 (2) |
C33B | 0.029 (2) | 0.048 (3) | 0.035 (3) | −0.015 (2) | 0.000 (2) | −0.008 (2) |
C34B | 0.028 (2) | 0.028 (2) | 0.023 (2) | −0.0039 (18) | −0.0064 (17) | −0.0042 (18) |
O34B | 0.0359 (18) | 0.0282 (18) | 0.0311 (18) | 0.0012 (14) | −0.0029 (14) | −0.0061 (14) |
N40B | 0.041 (2) | 0.027 (2) | 0.026 (2) | 0.0028 (18) | −0.0021 (17) | −0.0050 (17) |
C40B | 0.042 (3) | 0.033 (3) | 0.024 (2) | −0.003 (2) | −0.002 (2) | −0.0049 (19) |
C41B | 0.047 (3) | 0.030 (2) | 0.023 (2) | −0.004 (2) | −0.004 (2) | −0.0079 (18) |
O41B | 0.053 (3) | 0.040 (2) | 0.044 (2) | −0.0153 (19) | −0.0114 (19) | −0.0045 (18) |
O50B | 0.051 (2) | 0.033 (2) | 0.039 (2) | −0.0079 (17) | −0.0145 (18) | 0.0027 (16) |
C50B | 0.051 (2) | 0.038 (2) | 0.044 (2) | −0.0026 (18) | −0.017 (2) | −0.0055 (17) |
C51B | 0.052 (2) | 0.0357 (17) | 0.0370 (18) | 0.0080 (15) | −0.0070 (16) | −0.0073 (15) |
C52B | 0.069 (2) | 0.047 (2) | 0.045 (2) | 0.0071 (18) | −0.0204 (18) | −0.0077 (17) |
C53B | 0.094 (3) | 0.053 (2) | 0.053 (2) | 0.017 (2) | −0.027 (2) | −0.0015 (18) |
C54B | 0.080 (3) | 0.041 (2) | 0.064 (2) | 0.0042 (18) | −0.003 (2) | 0.0036 (19) |
C55B | 0.065 (2) | 0.041 (2) | 0.084 (3) | −0.0038 (18) | −0.010 (2) | −0.004 (2) |
C56B | 0.060 (2) | 0.0393 (19) | 0.064 (2) | −0.0007 (17) | −0.0207 (19) | −0.0001 (18) |
C10A—O10A | 1.475 (6) | C10B—O10B | 1.474 (7) |
C10A—C11A | 1.518 (9) | C10B—C11B | 1.515 (11) |
C10A—C12A | 1.520 (9) | C10B—C12B | 1.520 (9) |
C10A—C13A | 1.521 (9) | C10B—C13B | 1.528 (10) |
C11A—H11A | 0.9800 | C11B—H11B | 0.9800 |
C11A—H12A | 0.9800 | C11B—H12B | 0.9800 |
C11A—H13A | 0.9800 | C11B—H13B | 0.9800 |
C12A—H14A | 0.9800 | C12B—H14B | 0.9800 |
C12A—H15A | 0.9800 | C12B—H15B | 0.9800 |
C12A—H16A | 0.9800 | C12B—H16B | 0.9800 |
C13A—H17A | 0.9800 | C13B—H17B | 0.9800 |
C13A—H18A | 0.9800 | C13B—H18B | 0.9800 |
C13A—H19A | 0.9800 | C13B—H19B | 0.9800 |
O10A—C14A | 1.357 (7) | O10B—C14B | 1.360 (6) |
C14A—O14A | 1.210 (7) | C14B—O14B | 1.207 (7) |
C14A—N20A | 1.350 (7) | C14B—N20B | 1.342 (7) |
N20A—C20A | 1.451 (7) | N20B—C20B | 1.458 (6) |
N20A—H20A | 0.8800 | N20B—H20B | 0.8800 |
C20A—C21A | 1.532 (8) | C20B—C21B | 1.521 (8) |
C20A—C22A | 1.538 (7) | C20B—C22B | 1.538 (7) |
C20A—H21A | 1.0000 | C20B—H21B | 1.0000 |
C21A—H22A | 0.9800 | C21B—H22B | 0.9800 |
C21A—H23A | 0.9800 | C21B—H23B | 0.9800 |
C21A—H24A | 0.9800 | C21B—H24B | 0.9800 |
C22A—O22A | 1.227 (6) | C22B—O22B | 1.223 (6) |
C22A—N30A | 1.336 (6) | C22B—N30B | 1.340 (6) |
N30A—C30A | 1.461 (7) | N30B—C30B | 1.457 (6) |
N30A—C33A | 1.474 (8) | N30B—C33B | 1.476 (7) |
C30A—C34A | 1.526 (9) | C30B—C34B | 1.519 (7) |
C30A—C31A | 1.545 (9) | C30B—C31B | 1.545 (7) |
C30A—H30A | 1.0000 | C30B—H30B | 1.0000 |
C31A—C32A | 1.503 (13) | C31B—C32B | 1.519 (8) |
C31A—H33A | 0.9900 | C31B—H33B | 0.9900 |
C31A—H34A | 0.9900 | C31B—H34B | 0.9900 |
C32A—O32A | 1.412 (8) | C32B—O32B | 1.431 (8) |
C32A—C33A | 1.522 (9) | C32B—C33B | 1.514 (8) |
C32A—H35A | 1.0000 | C32B—H35B | 1.0000 |
O32A—H32A | 0.76 (8) | O32B—H32B | 0.85 (13) |
C33A—H36A | 0.9900 | C33B—H36B | 0.9900 |
C33A—H37A | 0.9900 | C33B—H37B | 0.9900 |
C34A—O34A | 1.222 (8) | C34B—O34B | 1.226 (6) |
C34A—N40A | 1.337 (8) | C34B—N40B | 1.345 (6) |
N40A—C40A | 1.441 (9) | N40B—C40B | 1.438 (7) |
N40A—H40A | 0.8800 | N40B—H40B | 0.8800 |
C40A—C41A | 1.510 (8) | C40B—C41B | 1.517 (8) |
C40A—H41A | 0.9900 | C40B—H41B | 0.9900 |
C40A—H42A | 0.9900 | C40B—H42B | 0.9900 |
C41A—O41A | 1.179 (8) | C41B—O41B | 1.199 (7) |
C41A—O50A | 1.329 (8) | C41B—O50B | 1.339 (7) |
O50A—C50A | 1.453 (11) | O50B—C50B | 1.437 (7) |
C50A—C51A | 1.500 (12) | C50B—C51B | 1.512 (9) |
C50A—H50A | 0.9900 | C50B—H50B | 0.9900 |
C50A—H51A | 0.9900 | C50B—H51B | 0.9900 |
C51A—C56A | 1.375 (13) | C51B—C56B | 1.389 (11) |
C51A—C52A | 1.376 (13) | C51B—C52B | 1.390 (9) |
C52A—C53A | 1.401 (17) | C52B—C53B | 1.403 (12) |
C52A—H52A | 0.9500 | C52B—H52B | 0.9500 |
C53A—C54A | 1.37 (2) | C53B—C54B | 1.372 (15) |
C53A—H53A | 0.9500 | C53B—H53B | 0.9500 |
C54A—C55A | 1.35 (2) | C54B—C55B | 1.367 (13) |
C54A—H54A | 0.9500 | C54B—H54B | 0.9500 |
C55A—C56A | 1.373 (16) | C55B—C56B | 1.395 (11) |
C55A—H55A | 0.9500 | C55B—H55B | 0.9500 |
C56A—H56A | 0.9500 | C56B—H56B | 0.9500 |
O10A—C10A—C11A | 101.8 (5) | O10B—C10B—C11B | 111.4 (5) |
O10A—C10A—C12A | 110.1 (5) | O10B—C10B—C12B | 109.5 (5) |
C11A—C10A—C12A | 110.6 (5) | C11B—C10B—C12B | 112.4 (7) |
O10A—C10A—C13A | 111.2 (5) | O10B—C10B—C13B | 101.4 (6) |
C11A—C10A—C13A | 111.1 (5) | C11B—C10B—C13B | 111.0 (6) |
C12A—C10A—C13A | 111.7 (5) | C12B—C10B—C13B | 110.5 (6) |
C10A—C11A—H11A | 109.5 | C10B—C11B—H11B | 109.5 |
C10A—C11A—H12A | 109.5 | C10B—C11B—H12B | 109.5 |
H11A—C11A—H12A | 109.5 | H11B—C11B—H12B | 109.5 |
C10A—C11A—H13A | 109.5 | C10B—C11B—H13B | 109.5 |
H11A—C11A—H13A | 109.5 | H11B—C11B—H13B | 109.5 |
H12A—C11A—H13A | 109.5 | H12B—C11B—H13B | 109.5 |
C10A—C12A—H14A | 109.5 | C10B—C12B—H14B | 109.5 |
C10A—C12A—H15A | 109.5 | C10B—C12B—H15B | 109.5 |
H14A—C12A—H15A | 109.5 | H14B—C12B—H15B | 109.5 |
C10A—C12A—H16A | 109.5 | C10B—C12B—H16B | 109.5 |
H14A—C12A—H16A | 109.5 | H14B—C12B—H16B | 109.5 |
H15A—C12A—H16A | 109.5 | H15B—C12B—H16B | 109.5 |
C10A—C13A—H17A | 109.5 | C10B—C13B—H17B | 109.5 |
C10A—C13A—H18A | 109.5 | C10B—C13B—H18B | 109.5 |
H17A—C13A—H18A | 109.5 | H17B—C13B—H18B | 109.5 |
C10A—C13A—H19A | 109.5 | C10B—C13B—H19B | 109.5 |
H17A—C13A—H19A | 109.5 | H17B—C13B—H19B | 109.5 |
H18A—C13A—H19A | 109.5 | H18B—C13B—H19B | 109.5 |
C14A—O10A—C10A | 120.6 (4) | C14B—O10B—C10B | 120.0 (5) |
O14A—C14A—N20A | 125.4 (5) | O14B—C14B—N20B | 124.6 (5) |
O14A—C14A—O10A | 125.5 (5) | O14B—C14B—O10B | 125.2 (5) |
N20A—C14A—O10A | 109.2 (4) | N20B—C14B—O10B | 110.1 (5) |
C14A—N20A—C20A | 120.7 (4) | C14B—N20B—C20B | 119.1 (5) |
C14A—N20A—H20A | 119.7 | C14B—N20B—H20B | 120.4 |
C20A—N20A—H20A | 119.7 | C20B—N20B—H20B | 120.4 |
N20A—C20A—C21A | 110.4 (5) | N20B—C20B—C21B | 110.1 (5) |
N20A—C20A—C22A | 110.9 (4) | N20B—C20B—C22B | 111.2 (4) |
C21A—C20A—C22A | 109.5 (4) | C21B—C20B—C22B | 109.1 (4) |
N20A—C20A—H21A | 108.7 | N20B—C20B—H21B | 108.8 |
C21A—C20A—H21A | 108.7 | C21B—C20B—H21B | 108.8 |
C22A—C20A—H21A | 108.7 | C22B—C20B—H21B | 108.8 |
C20A—C21A—H22A | 109.5 | C20B—C21B—H22B | 109.5 |
C20A—C21A—H23A | 109.5 | C20B—C21B—H23B | 109.5 |
H22A—C21A—H23A | 109.5 | H22B—C21B—H23B | 109.5 |
C20A—C21A—H24A | 109.5 | C20B—C21B—H24B | 109.5 |
H22A—C21A—H24A | 109.5 | H22B—C21B—H24B | 109.5 |
H23A—C21A—H24A | 109.5 | H23B—C21B—H24B | 109.5 |
O22A—C22A—N30A | 120.9 (5) | O22B—C22B—N30B | 122.5 (5) |
O22A—C22A—C20A | 121.8 (4) | O22B—C22B—C20B | 121.4 (4) |
N30A—C22A—C20A | 117.2 (4) | N30B—C22B—C20B | 116.0 (4) |
C22A—N30A—C30A | 120.2 (5) | C22B—N30B—C30B | 121.0 (4) |
C22A—N30A—C33A | 127.3 (5) | C22B—N30B—C33B | 126.7 (4) |
C30A—N30A—C33A | 112.1 (5) | C30B—N30B—C33B | 112.1 (4) |
N30A—C30A—C34A | 112.8 (5) | N30B—C30B—C34B | 113.7 (4) |
N30A—C30A—C31A | 103.2 (6) | N30B—C30B—C31B | 102.8 (4) |
C34A—C30A—C31A | 108.6 (5) | C34B—C30B—C31B | 108.3 (4) |
N30A—C30A—H30A | 110.7 | N30B—C30B—H30B | 110.6 |
C34A—C30A—H30A | 110.7 | C34B—C30B—H30B | 110.6 |
C31A—C30A—H30A | 110.7 | C31B—C30B—H30B | 110.6 |
C32A—C31A—C30A | 104.5 (5) | C32B—C31B—C30B | 102.8 (4) |
C32A—C31A—H33A | 110.9 | C32B—C31B—H33B | 111.2 |
C30A—C31A—H33A | 110.9 | C30B—C31B—H33B | 111.2 |
C32A—C31A—H34A | 110.9 | C32B—C31B—H34B | 111.2 |
C30A—C31A—H34A | 110.9 | C30B—C31B—H34B | 111.2 |
H33A—C31A—H34A | 108.9 | H33B—C31B—H34B | 109.1 |
O32A—C32A—C31A | 111.7 (7) | O32B—C32B—C33B | 108.4 (5) |
O32A—C32A—C33A | 106.9 (6) | O32B—C32B—C31B | 111.5 (5) |
C31A—C32A—C33A | 103.5 (6) | C33B—C32B—C31B | 103.7 (4) |
O32A—C32A—H35A | 111.5 | O32B—C32B—H35B | 111.0 |
C31A—C32A—H35A | 111.5 | C33B—C32B—H35B | 111.0 |
C33A—C32A—H35A | 111.5 | C31B—C32B—H35B | 111.0 |
C32A—O32A—H32A | 104 (6) | C32B—O32B—H32B | 106 (8) |
N30A—C33A—C32A | 102.7 (6) | N30B—C33B—C32B | 103.5 (5) |
N30A—C33A—H36A | 111.2 | N30B—C33B—H36B | 111.1 |
C32A—C33A—H36A | 111.2 | C32B—C33B—H36B | 111.1 |
N30A—C33A—H37A | 111.2 | N30B—C33B—H37B | 111.1 |
C32A—C33A—H37A | 111.2 | C32B—C33B—H37B | 111.1 |
H36A—C33A—H37A | 109.1 | H36B—C33B—H37B | 109.0 |
O34A—C34A—N40A | 123.0 (6) | O34B—C34B—N40B | 122.8 (4) |
O34A—C34A—C30A | 121.0 (6) | O34B—C34B—C30B | 123.6 (5) |
N40A—C34A—C30A | 115.8 (6) | N40B—C34B—C30B | 113.1 (4) |
C34A—N40A—C40A | 123.6 (6) | C34B—N40B—C40B | 119.4 (4) |
C34A—N40A—H40A | 118.2 | C34B—N40B—H40B | 120.3 |
C40A—N40A—H40A | 118.2 | C40B—N40B—H40B | 120.3 |
N40A—C40A—C41A | 112.1 (5) | N40B—C40B—C41B | 111.6 (5) |
N40A—C40A—H41A | 109.2 | N40B—C40B—H41B | 109.3 |
C41A—C40A—H41A | 109.2 | C41B—C40B—H41B | 109.3 |
N40A—C40A—H42A | 109.2 | N40B—C40B—H42B | 109.3 |
C41A—C40A—H42A | 109.2 | C41B—C40B—H42B | 109.3 |
H41A—C40A—H42A | 107.9 | H41B—C40B—H42B | 108.0 |
O41A—C41A—O50A | 124.4 (6) | O41B—C41B—O50B | 124.2 (5) |
O41A—C41A—C40A | 126.8 (6) | O41B—C41B—C40B | 127.2 (5) |
O50A—C41A—C40A | 108.9 (6) | O50B—C41B—C40B | 108.5 (5) |
C41A—O50A—C50A | 116.5 (6) | C41B—O50B—C50B | 117.6 (5) |
O50A—C50A—C51A | 110.1 (7) | O50B—C50B—C51B | 106.3 (5) |
O50A—C50A—H50A | 109.6 | O50B—C50B—H50B | 110.5 |
C51A—C50A—H50A | 109.6 | C51B—C50B—H50B | 110.5 |
O50A—C50A—H51A | 109.6 | O50B—C50B—H51B | 110.5 |
C51A—C50A—H51A | 109.6 | C51B—C50B—H51B | 110.5 |
H50A—C50A—H51A | 108.2 | H50B—C50B—H51B | 108.7 |
C56A—C51A—C52A | 119.7 (9) | C56B—C51B—C52B | 118.9 (7) |
C56A—C51A—C50A | 119.5 (9) | C56B—C51B—C50B | 122.3 (6) |
C52A—C51A—C50A | 120.8 (9) | C52B—C51B—C50B | 118.8 (7) |
C51A—C52A—C53A | 119.0 (10) | C51B—C52B—C53B | 119.5 (8) |
C51A—C52A—H52A | 120.5 | C51B—C52B—H52B | 120.3 |
C53A—C52A—H52A | 120.5 | C53B—C52B—H52B | 120.3 |
C54A—C53A—C52A | 119.7 (11) | C54B—C53B—C52B | 120.6 (8) |
C54A—C53A—H53A | 120.2 | C54B—C53B—H53B | 119.7 |
C52A—C53A—H53A | 120.2 | C52B—C53B—H53B | 119.7 |
C55A—C54A—C53A | 121.0 (10) | C55B—C54B—C53B | 120.3 (7) |
C55A—C54A—H54A | 119.5 | C55B—C54B—H54B | 119.8 |
C53A—C54A—H54A | 119.5 | C53B—C54B—H54B | 119.8 |
C54A—C55A—C56A | 119.7 (12) | C54B—C55B—C56B | 119.8 (8) |
C54A—C55A—H55A | 120.1 | C54B—C55B—H55B | 120.1 |
C56A—C55A—H55A | 120.1 | C56B—C55B—H55B | 120.1 |
C55A—C56A—C51A | 120.9 (11) | C51B—C56B—C55B | 120.8 (7) |
C55A—C56A—H56A | 119.6 | C51B—C56B—H56B | 119.6 |
C51A—C56A—H56A | 119.6 | C55B—C56B—H56B | 119.6 |
C11A—C10A—O10A—C14A | 179.9 (5) | C11B—C10B—O10B—C14B | 69.3 (7) |
C12A—C10A—O10A—C14A | −62.8 (7) | C12B—C10B—O10B—C14B | −55.7 (8) |
C13A—C10A—O10A—C14A | 61.5 (7) | C13B—C10B—O10B—C14B | −172.5 (5) |
C10A—O10A—C14A—O14A | −1.9 (8) | C10B—O10B—C14B—O14B | −16.0 (9) |
C10A—O10A—C14A—N20A | 178.8 (4) | C10B—O10B—C14B—N20B | 163.3 (5) |
O14A—C14A—N20A—C20A | 5.5 (8) | O14B—C14B—N20B—C20B | 1.0 (8) |
O10A—C14A—N20A—C20A | −175.2 (4) | O10B—C14B—N20B—C20B | −178.3 (4) |
C14A—N20A—C20A—C21A | 137.8 (5) | C14B—N20B—C20B—C21B | 162.8 (5) |
C14A—N20A—C20A—C22A | −100.6 (5) | C14B—N20B—C20B—C22B | −76.1 (6) |
N20A—C20A—C22A—O22A | −29.1 (7) | N20B—C20B—C22B—O22B | −39.4 (7) |
C21A—C20A—C22A—O22A | 92.9 (6) | C21B—C20B—C22B—O22B | 82.3 (6) |
N20A—C20A—C22A—N30A | 154.2 (4) | N20B—C20B—C22B—N30B | 144.2 (5) |
C21A—C20A—C22A—N30A | −83.7 (6) | C21B—C20B—C22B—N30B | −94.1 (6) |
O22A—C22A—N30A—C30A | 2.5 (8) | O22B—C22B—N30B—C30B | −1.6 (7) |
C20A—C22A—N30A—C30A | 179.1 (5) | C20B—C22B—N30B—C30B | 174.7 (4) |
O22A—C22A—N30A—C33A | 175.0 (6) | O22B—C22B—N30B—C33B | 173.2 (5) |
C20A—C22A—N30A—C33A | −8.3 (8) | C20B—C22B—N30B—C33B | −10.4 (7) |
C22A—N30A—C30A—C34A | −66.1 (7) | C22B—N30B—C30B—C34B | −53.8 (6) |
C33A—N30A—C30A—C34A | 120.3 (6) | C33B—N30B—C30B—C34B | 130.7 (5) |
C22A—N30A—C30A—C31A | 176.9 (5) | C22B—N30B—C30B—C31B | −170.6 (5) |
C33A—N30A—C30A—C31A | 3.3 (7) | C33B—N30B—C30B—C31B | 13.9 (6) |
N30A—C30A—C31A—C32A | −25.1 (8) | N30B—C30B—C31B—C32B | −32.3 (6) |
C34A—C30A—C31A—C32A | −145.1 (6) | C34B—C30B—C31B—C32B | −152.8 (5) |
C30A—C31A—C32A—O32A | −77.4 (7) | C30B—C31B—C32B—O32B | −77.3 (6) |
C30A—C31A—C32A—C33A | 37.2 (8) | C30B—C31B—C32B—C33B | 39.1 (6) |
C22A—N30A—C33A—C32A | −153.7 (6) | C22B—N30B—C33B—C32B | −165.0 (5) |
C30A—N30A—C33A—C32A | 19.3 (8) | C30B—N30B—C33B—C32B | 10.2 (6) |
O32A—C32A—C33A—N30A | 83.7 (8) | O32B—C32B—C33B—N30B | 88.1 (5) |
C31A—C32A—C33A—N30A | −34.4 (8) | C31B—C32B—C33B—N30B | −30.4 (6) |
N30A—C30A—C34A—O34A | −39.9 (7) | N30B—C30B—C34B—O34B | −33.9 (7) |
C31A—C30A—C34A—O34A | 73.9 (7) | C31B—C30B—C34B—O34B | 79.7 (6) |
N30A—C30A—C34A—N40A | 144.7 (5) | N30B—C30B—C34B—N40B | 153.6 (4) |
C31A—C30A—C34A—N40A | −101.5 (7) | C31B—C30B—C34B—N40B | −92.8 (5) |
O34A—C34A—N40A—C40A | −10.8 (9) | O34B—C34B—N40B—C40B | −8.7 (8) |
C30A—C34A—N40A—C40A | 164.4 (5) | C30B—C34B—N40B—C40B | 163.9 (4) |
C34A—N40A—C40A—C41A | −73.1 (8) | C34B—N40B—C40B—C41B | −58.6 (6) |
N40A—C40A—C41A—O41A | −18.6 (10) | N40B—C40B—C41B—O41B | −29.7 (8) |
N40A—C40A—C41A—O50A | 161.7 (6) | N40B—C40B—C41B—O50B | 152.9 (4) |
O41A—C41A—O50A—C50A | −6.7 (10) | O41B—C41B—O50B—C50B | −0.8 (8) |
C40A—C41A—O50A—C50A | 173.1 (6) | C40B—C41B—O50B—C50B | 176.7 (5) |
C41A—O50A—C50A—C51A | −87.9 (9) | C41B—O50B—C50B—C51B | −176.7 (5) |
O50A—C50A—C51A—C56A | −60.6 (10) | O50B—C50B—C51B—C56B | −17.8 (9) |
O50A—C50A—C51A—C52A | 120.7 (9) | O50B—C50B—C51B—C52B | 163.8 (6) |
C56A—C51A—C52A—C53A | 1.5 (12) | C56B—C51B—C52B—C53B | 1.8 (11) |
C50A—C51A—C52A—C53A | −179.8 (7) | C50B—C51B—C52B—C53B | −179.7 (7) |
C51A—C52A—C53A—C54A | 0.4 (14) | C51B—C52B—C53B—C54B | −0.3 (13) |
C52A—C53A—C54A—C55A | −1.7 (16) | C52B—C53B—C54B—C55B | −1.0 (14) |
C53A—C54A—C55A—C56A | 1.2 (18) | C53B—C54B—C55B—C56B | 0.7 (14) |
C54A—C55A—C56A—C51A | 0.7 (18) | C52B—C51B—C56B—C55B | −2.2 (12) |
C52A—C51A—C56A—C55A | −2.0 (14) | C50B—C51B—C56B—C55B | 179.4 (8) |
C50A—C51A—C56A—C55A | 179.2 (9) | C54B—C55B—C56B—C51B | 0.9 (14) |
Experimental details
(I) | (II) | |
Crystal data | ||
Chemical formula | C24H33N3O7 | C22H31N3O7 |
Mr | 475.53 | 449.50 |
Crystal system, space group | MonoclinicP21 | TriclinicP1 |
Temperature (K) | 200 | 200 |
a, b, c (Å) | 8.922 (2), 15.208 (3), 18.692 (4) | 5.8816 (3), 10.6294 (6), 19.707 (1) |
α, β, γ (°) | 90, 91.523 (3), 90 | 75.240 (1), 82.560 (1), 81.780 (1) |
V (Å3) | 2535.1 (9) | 1173.6 (1) |
Z | 4 | 2 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.10 |
Crystal size (mm) | 0.45 × 0.30 × 0.08 | 0.45 × 0.35 × 0.20 |
Data collection | ||
Diffractometer | Bruker SMART APEX area-detector diffractometer | Bruker AXS, SMART APEX CCD area detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.883, 0.993 | 0.927, 0.981 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21865, 5790, 4804 | 13595, 5142, 5049 |
Rint | 0.028 | 0.015 |
(sin θ/λ)max (Å−1) | 0.641 | 0.641 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.162, 1.11 | 0.038, 0.100, 1.02 |
No. of reflections | 5790 | 5142 |
No. of parameters | 627 | 593 |
No. of restraints | 279 | 245 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.51, −0.46 | 0.43, −0.16 |
Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SMART, SHELXS97 (Sheldrick, 1990), SHELXD (Sheldrick & Gould, 1995), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.
Bond | (IA) | (IB) | (IIA) | (IIB) | 1V7H* | |
C14—N20—C20—C22 | (φ1) | -71.1 (6) | -69.9 (7) | -100.6 (5) | -76.1 (6) | -70.0 |
N20—C20—C22—N30 | (ψ1) | 164.0 (4) | 174.2 (4) | 154.2 (4) | 144.2 (5) | 162.3 |
C22—N30—C30—C34 | (φ2) | -73.8 (4) | -63.1 (4) | -66.1 (7) | -53.8 (6) | -57.0 |
N30—C30—C34—N40 | (ψ2) | 148.8 (3) | 171.7 (3) | 144.7 (5) | 153.6 (4) | 149.6 |
C34—N40—C40—C41 | (φ3) | -70.9 (5) | -66.2 (5) | -73.1 (8) | -58.6 (6) | -71.1 |
N40—C40—C41—O50 | (ψ3) | 176.5 (4) | 179.2 (3) | 161.7 (6) | 152.9 (4) | 173.4 |
q2** | 0.340 (5) | 0.409 (5) | 0.365 (9) | 0.380 (7) | 0.353 | |
φ2** | 80.6 (7) | 285.6 (6) | 282 (1) | 267.1 (9) | 280.1 |
*PDB entry number: averaged torsion angles are from Okuyama et al.
(2004). **5-Membered ring-puckering parameters are defined by Cremer & Pople (1975), and calculated by PLATON (Spek, 2003). |
D—H···A | D—H | D···A | H···A | D—H···A |
(I) | ||||
N40A—H40A···O32B | 0.88 | 3.033 (5) | 2.18 | 162 |
N40B—H40B···O24A | 0.88 | 2.914 (4) | 2.06 | 163 |
O32B—H32B···O34Bi | 0.75 (7) | 2.729 (4) | 1.99 (8) | 172 (8) |
O32A—H32A···O24Bii | 0.80 (8) | 2.849 (5) | 2.12 (8) | 152 (8) |
(II) | ||||
O32A—H32A···O34B | 0.76 (8) | 2.807 (7) | 2.05 (8) | 175 (8) |
N20B—H20B···O41A | 0.88 | 3.073 (8) | 2.22 | 164 |
N40A—H40A···O32Biii | 0.88 | 2.844 (7) | 2.05 | 149 |
N20A—H20A···O41Biv | 0.88 | 3.196 (7) | 2.32 | 172 |
N40B—H40B···O22Av | 0.88 | 2.816 (6) | 1.94 | 173 |
O32B—H32B···O34Avi | 0.8 (1) | 2.666 (8) | 1.8 (1) | 172 (12) |
Symmetry codes: (i) -x, 1/2+y, 1-z; (ii) 1-x, 1/2+y, 1-z; (iii) x, 1+y, z; (iv) 1+x, 1+y, z; (v) x, y-1, z; (vi) x-1, y-1, z. |
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Collagen contains a characteristic amino acid sequence in which a Gly residue appears at every third position (X–Y–Gly). Moreover, the Pro–Hyp–Gly triplet (Hyp is 4-hydroxyproline) is frequently found as a repeating sequence, and earlier structural studies carried out with synthetic polypeptides [(Pro–Hyp–Gly)n] indicate that this repeating sequence assumes a triple-helical structure (Okuyama et al., 1998; Berisio et al., 2001; Okuyama et al., 2004). Here the protected triplet tert-butyloxycarbonyl—Pro–Hyp–Gly benzyl ester or Boc–Pro–Hyp–Gly–OBzl, (I), was used to investigate the structural characteristics of the collagen minimum repeating sequence. In addition, because (Ala–Hyp–Gly)n also shows collagen-like optical properties (Rao & Adams, 1979), the structure of Boc–Ala–Hyp–Gly–OBzl, (II), was used to investigate the contribution made by imino acids to the structure of the sequence.
For both (I) and (II), two independent peptide molecules (molecules A and B) are present in the crystal structure, where they are arranged antiparallel to one another and were slightly bent (Figs.1 and 2). Within the triple-helix of (Pro–Hyp–Gly)10, the averaged (φ, ψ) are approximately (-70°, 162°), (-57°, 150°) and (-71°, 173°) for the Pro, Hyp and Gly residues, respectively (Okuyama et al., 2004). Neither (I) nor (II) assume a triple-helical structure, though the torsion angles suggest conformational similarity to a triple helix, despite slight differences at the Ala residues of (II) (Table 1). The torsion angles also show structural similarity among (IA), (IB), (IIA) and (IIB). Molecular fitting revealed large deviations at the terminal tert-butyloxycarbonyl and benzyl ester groups (Fig. 3), but the conformation of the main chain was conserved among the four molecules. In addition, Hyp is an imino acid showing ring-puckering with the amplitudes q2 (Cremer & Pople, 1975) of 0.340 (5)–0.409 (5) Å. The ring-puckering parameter φ2 (N30—C30—C31—C32—C33) of 80.6 (7)° in (IA) differs from that of the other three molecules (Table 1). Nevertheless, the main chain conformation around the Hyp unit of (IA) is similar to that of the other molecules.
These peptide molecules, with their similar conformations, make up a sheet-like structure in the solid state (Figs. 4 and 5). Within the packing of (I), four hydrogen bonds are formed (Table 2); two are formed between the main chains (N40A···O32B and N40B···O24A); the remaining two involve the 4-hydroxy groups (O32). Atom O32B interacts with atoms N40A and O34B, acting as a hydrogen-bond acceptor and donor, respectively. By contrast, atom O32A acts only as a donor. Such hydroxyl group-related interactions contribute to the stabilization of the sheet-like structure of (I) (Fig. 4). Within (II), on the other hand, amide groups are situated within hydrogen-bonding range of the Ala and Gly residues (N20 and N40), so that four of the six hydrogen bonds formed are between the main chains (Table 2), which stabilizes the sheet-like structure (Fig. 5). Increases in such main chain–main chain interactions might be expected to affect the peptide structure, but superimposition showed only a slight deviation between Pro of (I) and Ala of (II) (Fig. 3). A different hydrogen-bonding mode also is observed for the hydroxyl groups of (II) (O32A and O32B). Within the triple helix of (Pro–Hyp–Gly)10, the 4-hydroxy groups of Hyp participate in hydrogen bonds with solvent molecules and intertriple helices, but not in interstrand interactions (Berisio et al., 2001; Kishimoto et al., 2005). It also was suggested that the 4-position of Hyp shows an inductive effect from 4-fluoroproline incorporated collagen-like peptide (Holmgren et al., 1998). It is noteworthy that the 4-hydroxy groups in both (I) and (II) play different roles in the hydrogen-bonding of molecules A and B.