Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270109049361/fn3037sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109049361/fn3037Isup2.hkl |
CCDC reference: 774897
Compound (I) was synthesized according to the literature procedure (Sengar et al., 2009). Colorless crystals suitable for X-ray analysis were obtained by slow evaporation of a methylene chloride solution of (I) in air.
H atoms were placed in calculated positions and refined using a riding model [Cmethyl—H = 0.97 Å, Cmethylene—H = 0.98 Å and Uiso(H) = 1.2Ueq(C)].
Data collection: SMART (Bruker, 2003); cell refinement: SMART (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Fig. 1. The molecular structure of (I), showing one of the molecules in the unit cell, with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted. |
C26H45N3O8 | Z = 4 |
Mr = 527.65 | F(000) = 1144 |
Triclinic, P1 | Dx = 1.175 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.1304 (17) Å | Cell parameters from 4387 reflections |
b = 15.250 (2) Å | θ = 2.3–24.7° |
c = 18.098 (3) Å | µ = 0.09 mm−1 |
α = 99.305 (4)° | T = 203 K |
β = 90.010 (3)° | Block, colorless |
γ = 100.168 (3)° | 0.24 × 0.18 × 0.13 mm |
V = 2982.5 (8) Å3 |
Bruker SMART APEX CCD diffractometer | 11582 independent reflections |
Radiation source: sealed tube | 7769 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
ω scans | θmax = 26.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −13→13 |
Tmin = 0.962, Tmax = 0.980 | k = −18→18 |
21467 measured reflections | l = −22→22 |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.078P)2] where P = (Fo2 + 2Fc2)/3 |
11582 reflections | (Δ/σ)max = 0.001 |
667 parameters | Δρmax = 0.58 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C26H45N3O8 | γ = 100.168 (3)° |
Mr = 527.65 | V = 2982.5 (8) Å3 |
Triclinic, P1 | Z = 4 |
a = 11.1304 (17) Å | Mo Kα radiation |
b = 15.250 (2) Å | µ = 0.09 mm−1 |
c = 18.098 (3) Å | T = 203 K |
α = 99.305 (4)° | 0.24 × 0.18 × 0.13 mm |
β = 90.010 (3)° |
Bruker SMART APEX CCD diffractometer | 11582 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | 7769 reflections with I > 2σ(I) |
Tmin = 0.962, Tmax = 0.980 | Rint = 0.052 |
21467 measured reflections |
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.58 e Å−3 |
11582 reflections | Δρmin = −0.22 e Å−3 |
667 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 | ||
N1 | 0.39731 (16) | 0.67232 (12) | 0.09461 (9) | 0.0377 (4) | |
O1 | 0.40064 (15) | 0.92475 (12) | 0.15327 (10) | 0.0543 (5) | |
C1 | 0.45976 (19) | 0.75264 (14) | 0.06693 (11) | 0.0347 (5) | |
H1A | 0.3987 | 0.7843 | 0.0494 | 0.042* | |
H1B | 0.5085 | 0.7340 | 0.0240 | 0.042* | |
N2 | 0.66007 (15) | 0.68993 (12) | 0.12598 (9) | 0.0350 (4) | |
C2 | 0.4616 (2) | 0.59587 (15) | 0.07647 (13) | 0.0452 (6) | |
H2A | 0.4865 | 0.5914 | 0.0243 | 0.054* | |
H2B | 0.4059 | 0.5399 | 0.0815 | 0.054* | |
O2 | 0.42055 (18) | 1.04161 (13) | 0.09357 (13) | 0.0813 (7) | |
O3 | 0.10887 (13) | 0.63734 (11) | −0.00927 (7) | 0.0422 (4) | |
N3 | 0.61348 (15) | 0.88656 (12) | 0.08799 (10) | 0.0386 (4) | |
C3 | 0.5738 (2) | 0.60575 (15) | 0.12716 (13) | 0.0445 (6) | |
H3A | 0.5477 | 0.6034 | 0.1786 | 0.053* | |
H3B | 0.6155 | 0.5546 | 0.1115 | 0.053* | |
C4 | 0.62026 (18) | 0.76784 (14) | 0.17081 (11) | 0.0333 (5) | |
H4A | 0.6926 | 0.8104 | 0.1928 | 0.040* | |
H4B | 0.5720 | 0.7473 | 0.2121 | 0.040* | |
O4 | 0.29145 (15) | 0.61343 (14) | −0.05496 (9) | 0.0609 (5) | |
N4 | 0.82517 (18) | 0.32138 (13) | 0.39869 (10) | 0.0437 (5) | |
O5 | 0.93958 (13) | 0.68547 (10) | 0.22990 (7) | 0.0386 (4) | |
C5 | 0.26748 (19) | 0.65231 (17) | 0.07875 (11) | 0.0418 (5) | |
H5A | 0.2322 | 0.7038 | 0.1028 | 0.050* | |
H5B | 0.2327 | 0.6003 | 0.1022 | 0.050* | |
N5 | 1.08196 (17) | 0.29854 (13) | 0.37395 (9) | 0.0397 (4) | |
O6 | 0.74587 (15) | 0.66414 (14) | 0.26987 (9) | 0.0579 (5) | |
C6 | 0.2270 (2) | 0.63181 (16) | −0.00387 (12) | 0.0395 (5) | |
N6 | 0.91778 (16) | 0.09754 (12) | 0.39427 (10) | 0.0384 (4) | |
O7 | 0.93936 (12) | 0.89762 (10) | 0.06443 (8) | 0.0381 (4) | |
C7 | 0.0418 (2) | 0.61897 (17) | −0.08259 (12) | 0.0438 (6) | |
O8 | 0.84142 (13) | 0.94627 (11) | 0.16839 (8) | 0.0464 (4) | |
C8 | 0.0965 (3) | 0.6853 (2) | −0.13176 (14) | 0.0663 (8) | |
H8A | 0.0950 | 0.7463 | −0.1065 | 0.099* | |
H8B | 0.0496 | 0.6739 | −0.1786 | 0.099* | |
H8C | 0.1803 | 0.6786 | −0.1419 | 0.099* | |
C9 | −0.0851 (2) | 0.6317 (2) | −0.05938 (14) | 0.0697 (9) | |
H9A | −0.0831 | 0.6939 | −0.0359 | 0.104* | |
H9B | −0.1143 | 0.5917 | −0.0241 | 0.104* | |
H9C | −0.1395 | 0.6178 | −0.1032 | 0.104* | |
O9 | 0.70047 (14) | 0.07270 (12) | 0.31403 (9) | 0.0505 (4) | |
C10 | 0.0413 (3) | 0.52294 (19) | −0.11932 (14) | 0.0612 (7) | |
H10A | 0.0039 | 0.4820 | −0.0866 | 0.092* | |
H10B | 0.1245 | 0.5142 | −0.1286 | 0.092* | |
H10C | −0.0049 | 0.5107 | −0.1664 | 0.092* | |
O10 | 0.64781 (17) | −0.05877 (14) | 0.35089 (11) | 0.0709 (6) | |
C11 | 0.78597 (19) | 0.68381 (16) | 0.14172 (11) | 0.0377 (5) | |
H11A | 0.8386 | 0.7374 | 0.1286 | 0.045* | |
H11B | 0.8057 | 0.6311 | 0.1085 | 0.045* | |
O11 | 0.55671 (15) | 0.35867 (12) | 0.50508 (8) | 0.0510 (4) | |
C12 | 0.8186 (2) | 0.67609 (15) | 0.22217 (12) | 0.0378 (5) | |
O12 | 0.74806 (17) | 0.36860 (17) | 0.54955 (9) | 0.0754 (6) | |
C13 | 0.9998 (2) | 0.68940 (16) | 0.30409 (11) | 0.0423 (5) | |
O13 | 1.36652 (14) | 0.30534 (12) | 0.27335 (8) | 0.0475 (4) | |
C14 | 0.9752 (3) | 0.7712 (2) | 0.35646 (14) | 0.0627 (7) | |
H14A | 0.8894 | 0.7628 | 0.3684 | 0.094* | |
H14B | 0.9959 | 0.8242 | 0.3326 | 0.094* | |
H14C | 1.0243 | 0.7793 | 0.4021 | 0.094* | |
O14 | 1.19095 (17) | 0.34162 (14) | 0.23709 (9) | 0.0601 (5) | |
C15 | 0.9594 (2) | 0.60264 (18) | 0.33431 (13) | 0.0553 (7) | |
H15A | 0.8738 | 0.5969 | 0.3463 | 0.083* | |
H15B | 1.0075 | 0.6033 | 0.3792 | 0.083* | |
H15C | 0.9710 | 0.5519 | 0.2969 | 0.083* | |
O15 | 1.23757 (14) | 0.08603 (11) | 0.42575 (8) | 0.0462 (4) | |
C16 | 1.1340 (2) | 0.7000 (2) | 0.28449 (14) | 0.0618 (7) | |
H16A | 1.1477 | 0.6464 | 0.2510 | 0.093* | |
H16B | 1.1837 | 0.7078 | 0.3299 | 0.093* | |
H16C | 1.1560 | 0.7524 | 0.2600 | 0.093* | |
O16 | 1.11896 (16) | 0.02944 (15) | 0.32270 (10) | 0.0677 (6) | |
C17 | 0.54374 (18) | 0.81800 (14) | 0.12679 (11) | 0.0328 (5) | |
C18 | 0.4664 (2) | 0.86554 (17) | 0.18453 (13) | 0.0457 (6) | |
H18A | 0.4081 | 0.8200 | 0.2048 | 0.055* | |
H18B | 0.5197 | 0.9006 | 0.2261 | 0.055* | |
C19 | 0.4689 (2) | 0.98670 (18) | 0.11756 (16) | 0.0564 (7) | |
C20 | 0.6003 (2) | 0.97978 (16) | 0.11063 (14) | 0.0480 (6) | |
H20A | 0.6369 | 1.0158 | 0.0735 | 0.058* | |
H20B | 0.6434 | 1.0040 | 0.1588 | 0.058* | |
C21 | 0.72624 (18) | 0.87247 (15) | 0.05463 (11) | 0.0365 (5) | |
H21A | 0.7340 | 0.8998 | 0.0090 | 0.044* | |
H21B | 0.7226 | 0.8074 | 0.0395 | 0.044* | |
C22 | 0.84106 (18) | 0.91027 (15) | 0.10394 (12) | 0.0350 (5) | |
C23 | 1.06572 (18) | 0.92773 (16) | 0.09735 (12) | 0.0382 (5) | |
C24 | 1.0815 (2) | 0.87568 (17) | 0.16025 (13) | 0.0480 (6) | |
H24A | 1.0315 | 0.8943 | 0.2018 | 0.072* | |
H24B | 1.1665 | 0.8879 | 0.1768 | 0.072* | |
H24C | 1.0564 | 0.8115 | 0.1424 | 0.072* | |
C25 | 1.1422 (2) | 0.89998 (19) | 0.03137 (13) | 0.0518 (6) | |
H25A | 1.1307 | 0.9340 | −0.0082 | 0.078* | |
H25B | 1.1172 | 0.8360 | 0.0129 | 0.078* | |
H25C | 1.2276 | 0.9122 | 0.0471 | 0.078* | |
C26 | 1.0907 (2) | 1.02814 (16) | 0.12306 (14) | 0.0497 (6) | |
H26A | 1.0793 | 1.0585 | 0.0811 | 0.075* | |
H26B | 1.1741 | 1.0469 | 0.1426 | 0.075* | |
H26C | 1.0348 | 1.0438 | 0.1621 | 0.075* | |
C27 | 0.8389 (2) | 0.23513 (16) | 0.41999 (11) | 0.0395 (5) | |
H27A | 0.7586 | 0.2034 | 0.4318 | 0.047* | |
H27B | 0.8909 | 0.2469 | 0.4655 | 0.047* | |
C28 | 0.9290 (2) | 0.39283 (17) | 0.42381 (13) | 0.0520 (6) | |
H28A | 0.9506 | 0.3906 | 0.4759 | 0.062* | |
H28B | 0.9053 | 0.4515 | 0.4224 | 0.062* | |
C29 | 1.0401 (2) | 0.38505 (17) | 0.37607 (13) | 0.0514 (6) | |
H29A | 1.0203 | 0.3921 | 0.3249 | 0.062* | |
H29B | 1.1069 | 0.4343 | 0.3959 | 0.062* | |
C30 | 1.00556 (19) | 0.22506 (15) | 0.32323 (11) | 0.0373 (5) | |
H30A | 1.0568 | 0.1817 | 0.3020 | 0.045* | |
H30B | 0.9758 | 0.2503 | 0.2817 | 0.045* | |
C31 | 0.7064 (2) | 0.34530 (19) | 0.41613 (12) | 0.0513 (7) | |
H31A | 0.6435 | 0.2977 | 0.3891 | 0.062* | |
H31B | 0.7018 | 0.4012 | 0.3969 | 0.062* | |
C32 | 0.6758 (2) | 0.35875 (18) | 0.49879 (13) | 0.0475 (6) | |
C33 | 0.4989 (2) | 0.3720 (2) | 0.57917 (12) | 0.0539 (7) | |
C34 | 0.5486 (4) | 0.4646 (2) | 0.61952 (18) | 0.0978 (12) | |
H34A | 0.6338 | 0.4684 | 0.6332 | 0.147* | |
H34B | 0.5028 | 0.4771 | 0.6644 | 0.147* | |
H34C | 0.5414 | 0.5084 | 0.5872 | 0.147* | |
C35 | 0.5158 (3) | 0.2981 (2) | 0.62185 (15) | 0.0715 (8) | |
H35A | 0.6011 | 0.3051 | 0.6366 | 0.107* | |
H35B | 0.4903 | 0.2399 | 0.5903 | 0.107* | |
H35C | 0.4667 | 0.3016 | 0.6662 | 0.107* | |
C36 | 0.3653 (3) | 0.3629 (3) | 0.55614 (16) | 0.0994 (14) | |
H36A | 0.3356 | 0.3021 | 0.5302 | 0.149* | |
H36B | 0.3572 | 0.4059 | 0.5232 | 0.149* | |
H36C | 0.3179 | 0.3749 | 0.6004 | 0.149* | |
C37 | 1.2114 (2) | 0.30377 (17) | 0.36034 (12) | 0.0448 (6) | |
H37A | 1.2348 | 0.2474 | 0.3696 | 0.054* | |
H37B | 1.2565 | 0.3527 | 0.3972 | 0.054* | |
C38 | 1.2529 (2) | 0.31952 (16) | 0.28246 (12) | 0.0415 (5) | |
C39 | 1.4270 (2) | 0.30619 (17) | 0.19957 (12) | 0.0457 (6) | |
C40 | 1.4436 (3) | 0.3985 (2) | 0.17940 (16) | 0.0782 (10) | |
H40A | 1.4925 | 0.4412 | 0.2182 | 0.117* | |
H40B | 1.3644 | 0.4157 | 0.1747 | 0.117* | |
H40C | 1.4846 | 0.3987 | 0.1321 | 0.117* | |
C41 | 1.5463 (3) | 0.2778 (3) | 0.21366 (17) | 0.0913 (12) | |
H41A | 1.5942 | 0.3227 | 0.2515 | 0.137* | |
H41B | 1.5909 | 0.2723 | 0.1676 | 0.137* | |
H41C | 1.5309 | 0.2200 | 0.2310 | 0.137* | |
C42 | 1.3514 (3) | 0.23747 (19) | 0.14101 (14) | 0.0624 (7) | |
H42A | 1.3902 | 0.2378 | 0.0930 | 0.094* | |
H42B | 1.2706 | 0.2523 | 0.1373 | 0.094* | |
H42C | 1.3447 | 0.1780 | 0.1549 | 0.094* | |
C43 | 0.89467 (19) | 0.17349 (15) | 0.35899 (11) | 0.0355 (5) | |
C44 | 0.8031 (2) | 0.13555 (17) | 0.29429 (12) | 0.0441 (6) | |
H44A | 0.7732 | 0.1856 | 0.2769 | 0.053* | |
H44B | 0.8447 | 0.1051 | 0.2527 | 0.053* | |
C45 | 0.7287 (2) | 0.00207 (18) | 0.34212 (14) | 0.0500 (6) | |
C46 | 0.8608 (2) | 0.00678 (16) | 0.36005 (14) | 0.0484 (6) | |
H46A | 0.8693 | −0.0355 | 0.3944 | 0.058* | |
H46B | 0.9027 | −0.0114 | 0.3140 | 0.058* | |
C47 | 1.0343 (2) | 0.10550 (16) | 0.43226 (11) | 0.0383 (5) | |
H47A | 1.0212 | 0.0744 | 0.4757 | 0.046* | |
H47B | 1.0644 | 0.1696 | 0.4512 | 0.046* | |
C48 | 1.1329 (2) | 0.06838 (17) | 0.38605 (13) | 0.0428 (6) | |
C49 | 1.3481 (2) | 0.05074 (17) | 0.39551 (13) | 0.0479 (6) | |
C50 | 1.3835 (2) | 0.0824 (2) | 0.32272 (15) | 0.0701 (8) | |
H50A | 1.3218 | 0.0539 | 0.2843 | 0.105* | |
H50B | 1.4616 | 0.0662 | 0.3080 | 0.105* | |
H50C | 1.3900 | 0.1474 | 0.3289 | 0.105* | |
C51 | 1.4440 (2) | 0.0938 (2) | 0.45603 (16) | 0.0694 (8) | |
H51A | 1.4203 | 0.0727 | 0.5026 | 0.104* | |
H51B | 1.4512 | 0.1589 | 0.4630 | 0.104* | |
H51C | 1.5219 | 0.0773 | 0.4413 | 0.104* | |
C52 | 1.3227 (3) | −0.0507 (2) | 0.38867 (19) | 0.0770 (9) | |
H52A | 1.2611 | −0.0760 | 0.3495 | 0.116* | |
H52B | 1.2936 | −0.0674 | 0.4359 | 0.116* | |
H52C | 1.3972 | −0.0739 | 0.3763 | 0.116* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0293 (10) | 0.0433 (11) | 0.0378 (9) | −0.0026 (8) | −0.0058 (7) | 0.0091 (8) |
O1 | 0.0310 (9) | 0.0551 (11) | 0.0763 (11) | 0.0155 (8) | 0.0008 (8) | 0.0004 (9) |
C1 | 0.0283 (11) | 0.0390 (12) | 0.0364 (11) | 0.0042 (9) | −0.0033 (8) | 0.0072 (9) |
N2 | 0.0289 (9) | 0.0374 (10) | 0.0403 (9) | 0.0059 (8) | −0.0035 (7) | 0.0113 (8) |
C2 | 0.0447 (14) | 0.0357 (13) | 0.0533 (13) | 0.0006 (11) | −0.0073 (11) | 0.0093 (11) |
O2 | 0.0545 (12) | 0.0533 (12) | 0.1420 (19) | 0.0251 (10) | −0.0150 (12) | 0.0167 (12) |
O3 | 0.0335 (8) | 0.0585 (10) | 0.0337 (8) | 0.0078 (7) | −0.0031 (6) | 0.0058 (7) |
N3 | 0.0249 (9) | 0.0374 (10) | 0.0557 (11) | 0.0060 (8) | 0.0013 (8) | 0.0136 (9) |
C3 | 0.0440 (14) | 0.0372 (13) | 0.0541 (14) | 0.0054 (11) | −0.0050 (11) | 0.0152 (11) |
C4 | 0.0260 (11) | 0.0400 (12) | 0.0342 (11) | 0.0045 (9) | 0.0000 (8) | 0.0087 (9) |
O4 | 0.0372 (9) | 0.1012 (15) | 0.0413 (9) | 0.0130 (10) | 0.0009 (7) | 0.0023 (9) |
N4 | 0.0486 (12) | 0.0486 (12) | 0.0404 (10) | 0.0202 (10) | 0.0133 (8) | 0.0141 (9) |
O5 | 0.0334 (8) | 0.0515 (10) | 0.0342 (8) | 0.0109 (7) | −0.0017 (6) | 0.0131 (7) |
C5 | 0.0314 (12) | 0.0531 (15) | 0.0374 (11) | −0.0026 (10) | 0.0007 (9) | 0.0081 (10) |
N5 | 0.0398 (11) | 0.0419 (11) | 0.0378 (10) | 0.0041 (9) | 0.0076 (8) | 0.0106 (8) |
O6 | 0.0398 (10) | 0.0997 (15) | 0.0435 (9) | 0.0195 (10) | 0.0085 (8) | 0.0318 (10) |
C6 | 0.0308 (12) | 0.0469 (14) | 0.0385 (12) | 0.0003 (10) | −0.0020 (9) | 0.0073 (10) |
N6 | 0.0325 (10) | 0.0396 (11) | 0.0448 (10) | 0.0072 (8) | −0.0015 (8) | 0.0113 (8) |
O7 | 0.0240 (8) | 0.0496 (9) | 0.0402 (8) | 0.0041 (7) | −0.0003 (6) | 0.0081 (7) |
C7 | 0.0377 (13) | 0.0598 (16) | 0.0341 (11) | 0.0095 (11) | −0.0080 (9) | 0.0077 (11) |
O8 | 0.0321 (9) | 0.0606 (11) | 0.0427 (9) | 0.0066 (8) | 0.0000 (7) | −0.0008 (8) |
C8 | 0.076 (2) | 0.076 (2) | 0.0474 (14) | 0.0078 (16) | −0.0093 (13) | 0.0191 (14) |
C9 | 0.0455 (16) | 0.119 (3) | 0.0474 (15) | 0.0267 (17) | −0.0081 (12) | 0.0088 (16) |
O9 | 0.0294 (9) | 0.0610 (11) | 0.0599 (10) | 0.0073 (8) | −0.0033 (7) | 0.0070 (9) |
C10 | 0.0570 (17) | 0.0648 (18) | 0.0543 (15) | 0.0009 (14) | −0.0162 (12) | −0.0012 (13) |
O10 | 0.0470 (11) | 0.0708 (14) | 0.0859 (14) | −0.0124 (10) | 0.0013 (10) | 0.0111 (11) |
C11 | 0.0328 (12) | 0.0476 (13) | 0.0376 (11) | 0.0141 (10) | 0.0016 (9) | 0.0141 (10) |
O11 | 0.0502 (10) | 0.0751 (12) | 0.0342 (8) | 0.0263 (9) | 0.0113 (7) | 0.0115 (8) |
C12 | 0.0344 (12) | 0.0424 (13) | 0.0405 (12) | 0.0138 (10) | 0.0011 (10) | 0.0110 (10) |
O12 | 0.0523 (12) | 0.138 (2) | 0.0380 (9) | 0.0244 (12) | 0.0040 (8) | 0.0126 (11) |
C13 | 0.0435 (13) | 0.0520 (14) | 0.0353 (11) | 0.0142 (11) | −0.0074 (9) | 0.0123 (10) |
O13 | 0.0367 (9) | 0.0681 (11) | 0.0368 (8) | 0.0008 (8) | 0.0046 (6) | 0.0155 (8) |
C14 | 0.0730 (19) | 0.0679 (19) | 0.0470 (14) | 0.0199 (15) | −0.0097 (13) | 0.0009 (13) |
O14 | 0.0583 (11) | 0.0885 (14) | 0.0449 (9) | 0.0266 (10) | 0.0100 (8) | 0.0300 (9) |
C15 | 0.0607 (17) | 0.0639 (17) | 0.0503 (14) | 0.0200 (14) | −0.0025 (12) | 0.0268 (13) |
O15 | 0.0361 (9) | 0.0564 (10) | 0.0484 (9) | 0.0157 (8) | −0.0065 (7) | 0.0068 (8) |
C16 | 0.0430 (15) | 0.093 (2) | 0.0542 (15) | 0.0152 (15) | −0.0095 (12) | 0.0222 (15) |
O16 | 0.0440 (10) | 0.1041 (16) | 0.0517 (11) | 0.0274 (10) | −0.0084 (8) | −0.0131 (10) |
C17 | 0.0228 (10) | 0.0376 (12) | 0.0377 (11) | 0.0045 (9) | −0.0011 (8) | 0.0067 (9) |
C18 | 0.0328 (12) | 0.0548 (15) | 0.0486 (13) | 0.0106 (11) | 0.0019 (10) | 0.0026 (11) |
C19 | 0.0392 (14) | 0.0414 (15) | 0.0855 (19) | 0.0120 (12) | −0.0116 (13) | −0.0040 (14) |
C20 | 0.0373 (13) | 0.0413 (14) | 0.0660 (15) | 0.0096 (11) | −0.0072 (11) | 0.0076 (12) |
C21 | 0.0302 (11) | 0.0445 (13) | 0.0371 (11) | 0.0059 (10) | 0.0025 (9) | 0.0146 (10) |
C22 | 0.0275 (11) | 0.0385 (12) | 0.0409 (12) | 0.0063 (9) | 0.0026 (9) | 0.0116 (10) |
C23 | 0.0207 (10) | 0.0470 (14) | 0.0477 (12) | 0.0016 (9) | 0.0025 (9) | 0.0148 (11) |
C24 | 0.0302 (12) | 0.0612 (16) | 0.0551 (14) | 0.0043 (11) | −0.0051 (10) | 0.0211 (12) |
C25 | 0.0320 (13) | 0.0714 (18) | 0.0518 (14) | 0.0078 (12) | 0.0008 (10) | 0.0112 (13) |
C26 | 0.0330 (13) | 0.0488 (15) | 0.0653 (15) | −0.0020 (11) | −0.0023 (11) | 0.0136 (12) |
C27 | 0.0374 (12) | 0.0486 (14) | 0.0364 (11) | 0.0117 (10) | 0.0054 (9) | 0.0142 (10) |
C28 | 0.0703 (18) | 0.0411 (14) | 0.0484 (14) | 0.0178 (13) | 0.0177 (12) | 0.0096 (11) |
C29 | 0.0601 (16) | 0.0441 (14) | 0.0506 (14) | 0.0065 (12) | 0.0172 (12) | 0.0126 (12) |
C30 | 0.0374 (12) | 0.0449 (13) | 0.0330 (11) | 0.0106 (10) | 0.0044 (9) | 0.0125 (10) |
C31 | 0.0598 (16) | 0.0668 (17) | 0.0374 (12) | 0.0347 (14) | 0.0124 (11) | 0.0133 (12) |
C32 | 0.0485 (15) | 0.0592 (16) | 0.0402 (13) | 0.0223 (12) | 0.0091 (11) | 0.0099 (11) |
C33 | 0.0551 (16) | 0.0779 (19) | 0.0341 (12) | 0.0248 (14) | 0.0151 (11) | 0.0105 (12) |
C34 | 0.128 (3) | 0.089 (3) | 0.068 (2) | 0.019 (2) | 0.043 (2) | −0.0113 (19) |
C35 | 0.073 (2) | 0.095 (2) | 0.0537 (16) | 0.0204 (18) | 0.0146 (14) | 0.0265 (16) |
C36 | 0.0568 (19) | 0.203 (4) | 0.0563 (17) | 0.052 (2) | 0.0207 (14) | 0.041 (2) |
C37 | 0.0384 (13) | 0.0559 (15) | 0.0389 (12) | −0.0007 (11) | 0.0038 (10) | 0.0140 (11) |
C38 | 0.0396 (13) | 0.0456 (14) | 0.0375 (12) | 0.0003 (11) | 0.0043 (10) | 0.0092 (10) |
C39 | 0.0396 (13) | 0.0582 (16) | 0.0366 (12) | −0.0014 (11) | 0.0089 (9) | 0.0115 (11) |
C40 | 0.107 (3) | 0.0531 (18) | 0.0632 (17) | −0.0160 (17) | 0.0390 (17) | 0.0081 (15) |
C41 | 0.0455 (18) | 0.171 (4) | 0.0659 (19) | 0.023 (2) | 0.0157 (14) | 0.042 (2) |
C42 | 0.0606 (18) | 0.0602 (18) | 0.0596 (16) | 0.0055 (14) | 0.0125 (13) | −0.0049 (14) |
C43 | 0.0324 (11) | 0.0420 (13) | 0.0350 (11) | 0.0103 (10) | 0.0032 (9) | 0.0111 (10) |
C44 | 0.0365 (13) | 0.0543 (15) | 0.0441 (12) | 0.0129 (11) | −0.0005 (10) | 0.0105 (11) |
C45 | 0.0396 (14) | 0.0531 (16) | 0.0534 (14) | 0.0037 (13) | 0.0018 (11) | 0.0023 (12) |
C46 | 0.0397 (14) | 0.0426 (14) | 0.0640 (15) | 0.0057 (11) | −0.0001 (11) | 0.0137 (12) |
C47 | 0.0384 (12) | 0.0456 (13) | 0.0342 (11) | 0.0102 (10) | −0.0013 (9) | 0.0129 (10) |
C48 | 0.0367 (13) | 0.0521 (15) | 0.0419 (13) | 0.0121 (11) | −0.0053 (10) | 0.0097 (11) |
C49 | 0.0315 (12) | 0.0575 (16) | 0.0586 (14) | 0.0188 (11) | −0.0037 (10) | 0.0093 (12) |
C50 | 0.0436 (16) | 0.103 (2) | 0.0724 (18) | 0.0328 (16) | 0.0083 (13) | 0.0194 (17) |
C51 | 0.0416 (15) | 0.088 (2) | 0.0769 (19) | 0.0185 (15) | −0.0125 (13) | 0.0017 (16) |
C52 | 0.0497 (17) | 0.063 (2) | 0.121 (3) | 0.0215 (15) | −0.0053 (17) | 0.0126 (18) |
N1—C5 | 1.442 (3) | C17—C18 | 1.527 (3) |
N1—C1 | 1.460 (3) | C18—H18A | 0.9800 |
N1—C2 | 1.467 (3) | C18—H18B | 0.9800 |
O1—C19 | 1.353 (3) | C19—C20 | 1.488 (3) |
O1—C18 | 1.439 (3) | C20—H20A | 0.9800 |
C1—C17 | 1.537 (3) | C20—H20B | 0.9800 |
C1—H1A | 0.9800 | C21—C22 | 1.528 (3) |
C1—H1B | 0.9800 | C21—H21A | 0.9800 |
N2—C11 | 1.452 (3) | C21—H21B | 0.9800 |
N2—C3 | 1.464 (3) | C23—C26 | 1.503 (3) |
N2—C4 | 1.463 (3) | C23—C24 | 1.516 (3) |
C2—C3 | 1.520 (3) | C23—C25 | 1.514 (3) |
C2—H2A | 0.9800 | C24—H24A | 0.9700 |
C2—H2B | 0.9800 | C24—H24B | 0.9700 |
O2—C19 | 1.207 (3) | C24—H24C | 0.9700 |
O3—C6 | 1.337 (2) | C25—H25A | 0.9700 |
O3—C7 | 1.484 (2) | C25—H25B | 0.9700 |
N3—C21 | 1.428 (3) | C25—H25C | 0.9700 |
N3—C20 | 1.448 (3) | C26—H26A | 0.9700 |
N3—C17 | 1.463 (3) | C26—H26B | 0.9700 |
C3—H3A | 0.9800 | C26—H26C | 0.9700 |
C3—H3B | 0.9800 | C27—C43 | 1.536 (3) |
C4—C17 | 1.540 (3) | C27—H27A | 0.9800 |
C4—H4A | 0.9800 | C27—H27B | 0.9800 |
C4—H4B | 0.9800 | C28—C29 | 1.520 (3) |
O4—C6 | 1.198 (3) | C28—H28A | 0.9800 |
N4—C31 | 1.454 (3) | C28—H28B | 0.9800 |
N4—C28 | 1.457 (3) | C29—H29A | 0.9800 |
N4—C27 | 1.462 (3) | C29—H29B | 0.9800 |
O5—C12 | 1.334 (2) | C30—C43 | 1.544 (3) |
O5—C13 | 1.488 (2) | C30—H30A | 0.9800 |
C5—C6 | 1.528 (3) | C30—H30B | 0.9800 |
C5—H5A | 0.9800 | C31—C32 | 1.523 (3) |
C5—H5B | 0.9800 | C31—H31A | 0.9800 |
N5—C37 | 1.452 (3) | C31—H31B | 0.9800 |
N5—C30 | 1.467 (3) | C33—C34 | 1.491 (4) |
N5—C29 | 1.469 (3) | C33—C35 | 1.503 (4) |
O6—C12 | 1.197 (3) | C33—C36 | 1.520 (4) |
N6—C47 | 1.444 (3) | C34—H34A | 0.9700 |
N6—C46 | 1.454 (3) | C34—H34B | 0.9700 |
N6—C43 | 1.469 (3) | C34—H34C | 0.9700 |
O7—C22 | 1.333 (2) | C35—H35A | 0.9700 |
O7—C23 | 1.492 (2) | C35—H35B | 0.9700 |
C7—C8 | 1.503 (4) | C35—H35C | 0.9700 |
C7—C10 | 1.506 (4) | C36—H36A | 0.9700 |
C7—C9 | 1.510 (3) | C36—H36B | 0.9700 |
O8—C22 | 1.206 (2) | C36—H36C | 0.9700 |
C8—H8A | 0.9700 | C37—C38 | 1.526 (3) |
C8—H8B | 0.9700 | C37—H37A | 0.9800 |
C8—H8C | 0.9700 | C37—H37B | 0.9800 |
C9—H9A | 0.9700 | C39—C40 | 1.491 (4) |
C9—H9B | 0.9700 | C39—C42 | 1.503 (3) |
C9—H9C | 0.9700 | C39—C41 | 1.502 (4) |
O9—C45 | 1.347 (3) | C40—H40A | 0.9700 |
O9—C44 | 1.441 (3) | C40—H40B | 0.9700 |
C10—H10A | 0.9700 | C40—H40C | 0.9700 |
C10—H10B | 0.9700 | C41—H41A | 0.9700 |
C10—H10C | 0.9700 | C41—H41B | 0.9700 |
O10—C45 | 1.204 (3) | C41—H41C | 0.9700 |
C11—C12 | 1.528 (3) | C42—H42A | 0.9700 |
C11—H11A | 0.9800 | C42—H42B | 0.9700 |
C11—H11B | 0.9800 | C42—H42C | 0.9700 |
O11—C32 | 1.330 (3) | C43—C44 | 1.522 (3) |
O11—C33 | 1.487 (3) | C44—H44A | 0.9800 |
O12—C32 | 1.194 (3) | C44—H44B | 0.9800 |
C13—C14 | 1.506 (3) | C45—C46 | 1.493 (3) |
C13—C15 | 1.509 (3) | C46—H46A | 0.9800 |
C13—C16 | 1.522 (3) | C46—H46B | 0.9800 |
O13—C38 | 1.326 (3) | C47—C48 | 1.514 (3) |
O13—C39 | 1.497 (3) | C47—H47A | 0.9800 |
C14—H14A | 0.9700 | C47—H47B | 0.9800 |
C14—H14B | 0.9700 | C49—C50 | 1.504 (4) |
C14—H14C | 0.9700 | C49—C52 | 1.507 (4) |
O14—C38 | 1.198 (3) | C49—C51 | 1.513 (3) |
C15—H15A | 0.9700 | C50—H50A | 0.9700 |
C15—H15B | 0.9700 | C50—H50B | 0.9700 |
C15—H15C | 0.9700 | C50—H50C | 0.9700 |
O15—C48 | 1.331 (3) | C51—H51A | 0.9700 |
O15—C49 | 1.497 (3) | C51—H51B | 0.9700 |
C16—H16A | 0.9700 | C51—H51C | 0.9700 |
C16—H16B | 0.9700 | C52—H52A | 0.9700 |
C16—H16C | 0.9700 | C52—H52B | 0.9700 |
O16—C48 | 1.199 (3) | C52—H52C | 0.9700 |
C5—N1—C1 | 113.88 (17) | H24B—C24—H24C | 109.5 |
C5—N1—C2 | 115.61 (18) | C23—C25—H25A | 109.5 |
C1—N1—C2 | 112.13 (17) | C23—C25—H25B | 109.5 |
C19—O1—C18 | 115.68 (18) | H25A—C25—H25B | 109.5 |
N1—C1—C17 | 112.80 (16) | C23—C25—H25C | 109.5 |
N1—C1—H1A | 109.0 | H25A—C25—H25C | 109.5 |
C17—C1—H1A | 109.0 | H25B—C25—H25C | 109.5 |
N1—C1—H1B | 109.0 | C23—C26—H26A | 109.5 |
C17—C1—H1B | 109.0 | C23—C26—H26B | 109.5 |
H1A—C1—H1B | 107.8 | H26A—C26—H26B | 109.5 |
C11—N2—C3 | 113.80 (17) | C23—C26—H26C | 109.5 |
C11—N2—C4 | 113.43 (16) | H26A—C26—H26C | 109.5 |
C3—N2—C4 | 112.42 (17) | H26B—C26—H26C | 109.5 |
N1—C2—C3 | 112.03 (18) | N4—C27—C43 | 113.62 (16) |
N1—C2—H2A | 109.2 | N4—C27—H27A | 108.8 |
C3—C2—H2A | 109.2 | C43—C27—H27A | 108.8 |
N1—C2—H2B | 109.2 | N4—C27—H27B | 108.8 |
C3—C2—H2B | 109.2 | C43—C27—H27B | 108.8 |
H2A—C2—H2B | 107.9 | H27A—C27—H27B | 107.7 |
C6—O3—C7 | 121.86 (16) | N4—C28—C29 | 112.69 (19) |
C21—N3—C20 | 115.96 (18) | N4—C28—H28A | 109.1 |
C21—N3—C17 | 120.15 (17) | C29—C28—H28A | 109.1 |
C20—N3—C17 | 118.45 (18) | N4—C28—H28B | 109.1 |
N2—C3—C2 | 113.11 (18) | C29—C28—H28B | 109.1 |
N2—C3—H3A | 109.0 | H28A—C28—H28B | 107.8 |
C2—C3—H3A | 109.0 | N5—C29—C28 | 113.17 (19) |
N2—C3—H3B | 109.0 | N5—C29—H29A | 108.9 |
C2—C3—H3B | 109.0 | C28—C29—H29A | 108.9 |
H3A—C3—H3B | 107.8 | N5—C29—H29B | 108.9 |
N2—C4—C17 | 114.40 (15) | C28—C29—H29B | 108.9 |
N2—C4—H4A | 108.7 | H29A—C29—H29B | 107.8 |
C17—C4—H4A | 108.7 | N5—C30—C43 | 115.51 (16) |
N2—C4—H4B | 108.7 | N5—C30—H30A | 108.4 |
C17—C4—H4B | 108.7 | C43—C30—H30A | 108.4 |
H4A—C4—H4B | 107.6 | N5—C30—H30B | 108.4 |
C31—N4—C28 | 114.8 (2) | C43—C30—H30B | 108.4 |
C31—N4—C27 | 113.08 (19) | H30A—C30—H30B | 107.5 |
C28—N4—C27 | 112.45 (18) | N4—C31—C32 | 115.91 (19) |
C12—O5—C13 | 121.42 (16) | N4—C31—H31A | 108.3 |
N1—C5—C6 | 116.49 (17) | C32—C31—H31A | 108.3 |
N1—C5—H5A | 108.2 | N4—C31—H31B | 108.3 |
C6—C5—H5A | 108.2 | C32—C31—H31B | 108.3 |
N1—C5—H5B | 108.2 | H31A—C31—H31B | 107.4 |
C6—C5—H5B | 108.2 | O12—C32—O11 | 125.8 (2) |
H5A—C5—H5B | 107.3 | O12—C32—C31 | 125.0 (2) |
C37—N5—C30 | 112.76 (17) | O11—C32—C31 | 109.2 (2) |
C37—N5—C29 | 113.53 (19) | O11—C33—C34 | 109.0 (2) |
C30—N5—C29 | 112.04 (18) | O11—C33—C35 | 110.2 (2) |
O4—C6—O3 | 126.13 (19) | C34—C33—C35 | 113.8 (2) |
O4—C6—C5 | 125.0 (2) | O11—C33—C36 | 101.52 (19) |
O3—C6—C5 | 108.90 (17) | C34—C33—C36 | 111.4 (3) |
C47—N6—C46 | 115.95 (17) | C35—C33—C36 | 110.3 (3) |
C47—N6—C43 | 118.34 (18) | C33—C34—H34A | 109.5 |
C46—N6—C43 | 118.06 (17) | C33—C34—H34B | 109.5 |
C22—O7—C23 | 122.05 (16) | H34A—C34—H34B | 109.5 |
O3—C7—C8 | 110.53 (19) | C33—C34—H34C | 109.5 |
O3—C7—C10 | 109.85 (19) | H34A—C34—H34C | 109.5 |
C8—C7—C10 | 111.7 (2) | H34B—C34—H34C | 109.5 |
O3—C7—C9 | 101.82 (17) | C33—C35—H35A | 109.5 |
C8—C7—C9 | 111.9 (2) | C33—C35—H35B | 109.5 |
C10—C7—C9 | 110.6 (2) | H35A—C35—H35B | 109.5 |
C7—C8—H8A | 109.5 | C33—C35—H35C | 109.5 |
C7—C8—H8B | 109.5 | H35A—C35—H35C | 109.5 |
H8A—C8—H8B | 109.5 | H35B—C35—H35C | 109.5 |
C7—C8—H8C | 109.5 | C33—C36—H36A | 109.5 |
H8A—C8—H8C | 109.5 | C33—C36—H36B | 109.5 |
H8B—C8—H8C | 109.5 | H36A—C36—H36B | 109.5 |
C7—C9—H9A | 109.5 | C33—C36—H36C | 109.5 |
C7—C9—H9B | 109.5 | H36A—C36—H36C | 109.5 |
H9A—C9—H9B | 109.5 | H36B—C36—H36C | 109.5 |
C7—C9—H9C | 109.5 | N5—C37—C38 | 116.59 (18) |
H9A—C9—H9C | 109.5 | N5—C37—H37A | 108.1 |
H9B—C9—H9C | 109.5 | C38—C37—H37A | 108.1 |
C45—O9—C44 | 115.40 (18) | N5—C37—H37B | 108.1 |
C7—C10—H10A | 109.5 | C38—C37—H37B | 108.1 |
C7—C10—H10B | 109.5 | H37A—C37—H37B | 107.3 |
H10A—C10—H10B | 109.5 | O14—C38—O13 | 125.9 (2) |
C7—C10—H10C | 109.5 | O14—C38—C37 | 124.3 (2) |
H10A—C10—H10C | 109.5 | O13—C38—C37 | 109.80 (19) |
H10B—C10—H10C | 109.5 | C40—C39—O13 | 110.1 (2) |
N2—C11—C12 | 116.68 (17) | C40—C39—C42 | 111.5 (2) |
N2—C11—H11A | 108.1 | O13—C39—C42 | 109.13 (19) |
C12—C11—H11A | 108.1 | C40—C39—C41 | 112.5 (3) |
N2—C11—H11B | 108.1 | O13—C39—C41 | 102.93 (18) |
C12—C11—H11B | 108.1 | C42—C39—C41 | 110.3 (2) |
H11A—C11—H11B | 107.3 | C39—C40—H40A | 109.5 |
C32—O11—C33 | 122.05 (18) | C39—C40—H40B | 109.5 |
O6—C12—O5 | 126.41 (19) | H40A—C40—H40B | 109.5 |
O6—C12—C11 | 124.6 (2) | C39—C40—H40C | 109.5 |
O5—C12—C11 | 108.99 (17) | H40A—C40—H40C | 109.5 |
O5—C13—C14 | 109.27 (18) | H40B—C40—H40C | 109.5 |
O5—C13—C15 | 110.80 (19) | C39—C41—H41A | 109.5 |
C14—C13—C15 | 112.8 (2) | C39—C41—H41B | 109.5 |
O5—C13—C16 | 101.91 (17) | H41A—C41—H41B | 109.5 |
C14—C13—C16 | 110.9 (2) | C39—C41—H41C | 109.5 |
C15—C13—C16 | 110.6 (2) | H41A—C41—H41C | 109.5 |
C38—O13—C39 | 121.81 (17) | H41B—C41—H41C | 109.5 |
C13—C14—H14A | 109.5 | C39—C42—H42A | 109.5 |
C13—C14—H14B | 109.5 | C39—C42—H42B | 109.5 |
H14A—C14—H14B | 109.5 | H42A—C42—H42B | 109.5 |
C13—C14—H14C | 109.5 | C39—C42—H42C | 109.5 |
H14A—C14—H14C | 109.5 | H42A—C42—H42C | 109.5 |
H14B—C14—H14C | 109.5 | H42B—C42—H42C | 109.5 |
C13—C15—H15A | 109.5 | N6—C43—C44 | 107.73 (18) |
C13—C15—H15B | 109.5 | N6—C43—C27 | 105.51 (15) |
H15A—C15—H15B | 109.5 | C44—C43—C27 | 110.47 (17) |
C13—C15—H15C | 109.5 | N6—C43—C30 | 115.95 (16) |
H15A—C15—H15C | 109.5 | C44—C43—C30 | 104.77 (16) |
H15B—C15—H15C | 109.5 | C27—C43—C30 | 112.36 (18) |
C48—O15—C49 | 121.24 (17) | O9—C44—C43 | 113.18 (17) |
C13—C16—H16A | 109.5 | O9—C44—H44A | 108.9 |
C13—C16—H16B | 109.5 | C43—C44—H44A | 108.9 |
H16A—C16—H16B | 109.5 | O9—C44—H44B | 108.9 |
C13—C16—H16C | 109.5 | C43—C44—H44B | 108.9 |
H16A—C16—H16C | 109.5 | H44A—C44—H44B | 107.8 |
H16B—C16—H16C | 109.5 | O10—C45—O9 | 118.8 (2) |
N3—C17—C18 | 107.69 (18) | O10—C45—C46 | 125.4 (3) |
N3—C17—C1 | 106.21 (16) | O9—C45—C46 | 115.8 (2) |
C18—C17—C1 | 109.58 (17) | N6—C46—C45 | 111.20 (19) |
N3—C17—C4 | 115.56 (16) | N6—C46—H46A | 109.4 |
C18—C17—C4 | 105.89 (16) | C45—C46—H46A | 109.4 |
C1—C17—C4 | 111.79 (17) | N6—C46—H46B | 109.4 |
O1—C18—C17 | 112.43 (18) | C45—C46—H46B | 109.4 |
O1—C18—H18A | 109.1 | H46A—C46—H46B | 108.0 |
C17—C18—H18A | 109.1 | N6—C47—C48 | 116.20 (17) |
O1—C18—H18B | 109.1 | N6—C47—H47A | 108.2 |
C17—C18—H18B | 109.1 | C48—C47—H47A | 108.2 |
H18A—C18—H18B | 107.9 | N6—C47—H47B | 108.2 |
O2—C19—O1 | 119.1 (2) | C48—C47—H47B | 108.2 |
O2—C19—C20 | 125.3 (3) | H47A—C47—H47B | 107.4 |
O1—C19—C20 | 115.6 (2) | O16—C48—O15 | 125.0 (2) |
N3—C20—C19 | 110.4 (2) | O16—C48—C47 | 124.9 (2) |
N3—C20—H20A | 109.6 | O15—C48—C47 | 110.09 (19) |
C19—C20—H20A | 109.6 | O15—C49—C50 | 111.02 (18) |
N3—C20—H20B | 109.6 | O15—C49—C52 | 108.5 (2) |
C19—C20—H20B | 109.6 | C50—C49—C52 | 112.9 (2) |
H20A—C20—H20B | 108.1 | O15—C49—C51 | 102.05 (19) |
N3—C21—C22 | 115.78 (17) | C50—C49—C51 | 110.2 (2) |
N3—C21—H21A | 108.3 | C52—C49—C51 | 111.6 (2) |
C22—C21—H21A | 108.3 | C49—C50—H50A | 109.5 |
N3—C21—H21B | 108.3 | C49—C50—H50B | 109.5 |
C22—C21—H21B | 108.3 | H50A—C50—H50B | 109.5 |
H21A—C21—H21B | 107.4 | C49—C50—H50C | 109.5 |
O8—C22—O7 | 125.89 (19) | H50A—C50—H50C | 109.5 |
O8—C22—C21 | 124.74 (18) | H50B—C50—H50C | 109.5 |
O7—C22—C21 | 109.37 (17) | C49—C51—H51A | 109.5 |
O7—C23—C26 | 110.53 (17) | C49—C51—H51B | 109.5 |
O7—C23—C24 | 108.95 (17) | H51A—C51—H51B | 109.5 |
C26—C23—C24 | 112.4 (2) | C49—C51—H51C | 109.5 |
O7—C23—C25 | 101.67 (17) | H51A—C51—H51C | 109.5 |
C26—C23—C25 | 111.9 (2) | H51B—C51—H51C | 109.5 |
C24—C23—C25 | 110.86 (19) | C49—C52—H52A | 109.5 |
C23—C24—H24A | 109.5 | C49—C52—H52B | 109.5 |
C23—C24—H24B | 109.5 | H52A—C52—H52B | 109.5 |
H24A—C24—H24B | 109.5 | C49—C52—H52C | 109.5 |
C23—C24—H24C | 109.5 | H52A—C52—H52C | 109.5 |
H24A—C24—H24C | 109.5 | H52B—C52—H52C | 109.5 |
Experimental details
Crystal data | |
Chemical formula | C26H45N3O8 |
Mr | 527.65 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 203 |
a, b, c (Å) | 11.1304 (17), 15.250 (2), 18.098 (3) |
α, β, γ (°) | 99.305 (4), 90.010 (3), 100.168 (3) |
V (Å3) | 2982.5 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.24 × 0.18 × 0.13 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2003) |
Tmin, Tmax | 0.962, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21467, 11582, 7769 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.170, 1.04 |
No. of reflections | 11582 |
No. of parameters | 667 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.58, −0.22 |
Computer programs: SMART (Bruker, 2003), SAINT-Plus (Bruker, 2003), SHELXTL (Sheldrick, 2008).
Similar calculation for AAZTA chelate gave values for comparison. |
diazepane ring | morpholine ring | AAZTA | |||
q2 | 0.510 | 0.537 | 0.638 | 0.653 | 0.641 |
q3 | 0.676 | 0.675 | 0.031 | 0.026 | 0.633 |
θ2 | 69.0 | 67.2 | 55.1 | 59.3 | 65.7 |
θ3 | 323.7 | 323.5 | 16.2 |
X-ray cif was obtained from Cambridge Crystal Data Centre #650378 (Aime et al., 2008). |
The chemistry of 1,4-diazepane-based ligands is attracting increasing attention since these ligands have strong binding capabilities with different metal ions, including main group metals, transition metals and lanthanides (Comba et al., 2009, Ge et al., 2007, 2009; Peralta et al., 2005; Rey et al., 2007). In particular, it has been proposed that gadolinium(III) complexes of 6-amino-6-methylperhydro-1,4-diazepinetetraaceticacid (AAZTA) ligands are good candidates as MRI contrast agents due to their good thermodynamic stability, kinetic inertness and high relaxivity at neutral pH (Aime et al., 2004).
Recently, we reported the syntheses and characterization of new bifunctional AAZTA ligands with hyroxy side chains, and the crystal structures of gadolinium and europium complexes (Sengar et al., 2008, 2009). The title compound, (I), was used as a precursor for one of the bifunctional ligands with a hydroxy arm and the complete synthesis and spectroscopic characterization of (I) was provided (Sengar et al., 2009). Herein we report the molecular structure of compound (I) determined by X-ray crystallography (Fig. 1).
Compound (I) crystallizes with two independent molecules in the asymmetric cell unit, having nearly similar [change to: identical?] conformations . As expected, compound (I) contains two cyclic rings: a seven-membered 1,4-diazepane ring with a twisted-chair conformation and a six-membered oxomorpholine ring which adopts a boat conformation (Fig. 1). Both rings are connected to each other via one C atom in such a way that the mean planes of both rings are nearly orthogonal to each other. The diazepane and morpholine rings in both structures have slightly different puckering parameters (Cremer & Pople, 1975) as given in Table 1. The puckering parameters for the seven-membered ring in (I) are different to the values for the AAZTA chelate (Table 1) or the protonated diazepane (daza-3HCl-3H2O) chelate (Romba et al., 2005). This shows that the large flexibility is associated with the diazepane ring, and gives rise to the different puckering constants for non-coordinated ligands. However, upon metal coordination, the diazepane ring adopts a pseudo-chair conformation and all three N atoms coordinate to the metal ion in facial mode.
The C—N bond distances (N6—C43, N5—C30, N5—C29, N4—C27, N4—C28) in (I) are very similar [average distance ~1.465 (3) Å] for the exocyclic and endocyclic N atoms with respect to the diazepane ring. Interestingly, in the crystal structures of the metal complexes with such ligands, the exocyclic Nexo—C(ring) bond length becomes slightly longer compared with the endocyclic Nendo—C(ring) bond length. This may be due to the geometric constraint imposed by the coordinated metal ion.