Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106052474/jz3047sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270106052474/jz3047Isup2.hkl |
CCDC reference: 634906
The title peptide was obtained from Bachem. Crystals in the shape of extremely thin plates were obtained by slow evaporation of an aqueous solution.
H atoms were positioned with idealized geometry, with amide H atoms in the peptide plane, and fixed C—H and N—H distances of 0.98–1.00 Å and 0.88–0.91 Å, respectively. [Please check added text] Rigid rotation was permitted for amino groups only. Uiso(H) values were 1.2Ueq of the carrier atom, or 1.5Ueq(parent) for amino and methyl groups. In the absence of significant anomalous scattering effects, 4887 Friedel pairs were merged. The absolute configuration was known for the purchased material.
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C7H14N2O3 | Dx = 1.251 Mg m−3 |
Mr = 174.20 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 4643 reflections |
a = 5.5238 (7) Å | θ = 0.9–25.0° |
b = 26.581 (3) Å | µ = 0.10 mm−1 |
c = 44.093 (5) Å | T = 105 K |
V = 6474.0 (14) Å3 | Plate, colourless |
Z = 28 | 0.75 × 0.25 × 0.01 mm |
F(000) = 2632 |
Siemens SMART CCD area-detector diffractometer | 4122 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.125 |
Graphite monochromator | θmax = 25.0°, θmin = 0.9° |
Detector resolution: 8.3 pixels mm-1 | h = −6→6 |
ω scans | k = −31→31 |
35141 measured reflections | l = −52→39 |
6579 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.073 | H-atom parameters constrained |
wR(F2) = 0.172 | w = 1/[σ2(Fo2) + (0.048P)2 + 2.98P] where P = (Fo2 + 2Fc2)/3 |
S = 1.28 | (Δ/σ)max = 0.009 |
6579 reflections | Δρmax = 0.34 e Å−3 |
765 parameters | Δρmin = −0.35 e Å−3 |
1101 restraints | Extinction correction: SHELXTL (Bruker, 2000), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00086 (13) |
C7H14N2O3 | V = 6474.0 (14) Å3 |
Mr = 174.20 | Z = 28 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.5238 (7) Å | µ = 0.10 mm−1 |
b = 26.581 (3) Å | T = 105 K |
c = 44.093 (5) Å | 0.75 × 0.25 × 0.01 mm |
Siemens SMART CCD area-detector diffractometer | 4122 reflections with I > 2σ(I) |
35141 measured reflections | Rint = 0.125 |
6579 independent reflections |
R[F2 > 2σ(F2)] = 0.073 | 1101 restraints |
wR(F2) = 0.172 | H-atom parameters constrained |
S = 1.28 | Δρmax = 0.34 e Å−3 |
6579 reflections | Δρmin = −0.35 e Å−3 |
765 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. Data were collected by measuring three sets of exposures with the detector set at 2θ = 29°, crystal-to-detector distance 5.00 cm. Refinement of F2 against ALL reflections. |
x | y | z | Uiso*/Ueq | ||
O1A | 0.6208 (7) | 0.69919 (15) | 0.09435 (9) | 0.0254 (11) | |
O2A | 0.6337 (8) | 0.70171 (15) | 0.01811 (10) | 0.0335 (12) | |
O3A | 0.9653 (7) | 0.65673 (17) | 0.02741 (10) | 0.0329 (12) | |
N1A | 0.2233 (9) | 0.73321 (17) | 0.12486 (9) | 0.0190 (12) | |
H1A | 0.1215 | 0.7151 | 0.1369 | 0.029* | |
H2A | 0.1854 | 0.7665 | 0.1262 | 0.029* | |
H3A | 0.3787 | 0.7284 | 0.1311 | 0.029* | |
N2A | 0.3894 (8) | 0.65230 (15) | 0.06289 (10) | 0.0229 (13) | |
H4A | 0.2414 | 0.6432 | 0.0579 | 0.027* | |
C1A | 0.1975 (8) | 0.7163 (2) | 0.09304 (11) | 0.0206 (15) | |
H11A | 0.1729 | 0.7458 | 0.0797 | 0.025* | |
H12A | 0.0546 | 0.6941 | 0.0911 | 0.025* | |
C2A | 0.4222 (8) | 0.68836 (18) | 0.08358 (11) | 0.0183 (15) | |
C3A | 0.5944 (9) | 0.62784 (14) | 0.04847 (10) | 0.0239 (16) | |
H31A | 0.7009 | 0.6139 | 0.0648 | 0.029* | |
C4A | 0.5012 (10) | 0.58368 (17) | 0.02936 (12) | 0.0301 (18) | |
H41A | 0.3785 | 0.5973 | 0.0148 | 0.036* | |
C5A | 0.3745 (13) | 0.5454 (2) | 0.04936 (14) | 0.0353 (18) | |
H51A | 0.2457 | 0.5621 | 0.0609 | 0.053* | |
H52A | 0.4917 | 0.5306 | 0.0634 | 0.053* | |
H53A | 0.3041 | 0.5189 | 0.0367 | 0.053* | |
C6A | 0.6993 (13) | 0.5588 (2) | 0.01082 (15) | 0.048 (2) | |
H61A | 0.7754 | 0.5839 | −0.0024 | 0.072* | |
H62A | 0.6292 | 0.5320 | −0.0016 | 0.072* | |
H63A | 0.8213 | 0.5446 | 0.0245 | 0.072* | |
C7A | 0.7441 (8) | 0.66531 (18) | 0.02976 (13) | 0.0278 (17) | |
O1B | 0.5819 (8) | 0.6690 (2) | 0.23788 (10) | 0.0408 (14) | |
O2B | 0.6172 (7) | 0.72008 (13) | 0.16550 (9) | 0.0219 (11) | |
O3B | 0.9606 (6) | 0.67655 (14) | 0.16456 (10) | 0.0230 (11) | |
N1B | 0.1862 (10) | 0.6993 (2) | 0.26730 (9) | 0.0272 (14) | |
H1B | 0.0686 | 0.6861 | 0.2794 | 0.041* | |
H2B | 0.1754 | 0.7335 | 0.2675 | 0.041* | |
H3B | 0.3340 | 0.6898 | 0.2743 | 0.041* | |
N2B | 0.3838 (8) | 0.64530 (16) | 0.19511 (8) | 0.0235 (13) | |
H4B | 0.2418 | 0.6405 | 0.1865 | 0.028* | |
C1B | 0.1545 (9) | 0.6808 (3) | 0.23598 (12) | 0.0359 (19) | |
H11B | 0.0864 | 0.7080 | 0.2232 | 0.043* | |
H12B | 0.0394 | 0.6523 | 0.2359 | 0.043* | |
C2B | 0.3943 (9) | 0.6641 (2) | 0.22321 (10) | 0.0252 (16) | |
C3B | 0.6024 (8) | 0.63273 (15) | 0.17846 (10) | 0.0200 (15) | |
H31B | 0.7104 | 0.6131 | 0.1923 | 0.024* | |
C4B | 0.5376 (10) | 0.59910 (16) | 0.15142 (11) | 0.0219 (15) | |
H41B | 0.4197 | 0.6180 | 0.1385 | 0.026* | |
C5B | 0.4136 (13) | 0.5512 (2) | 0.16192 (15) | 0.042 (2) | |
H51B | 0.3705 | 0.5307 | 0.1442 | 0.063* | |
H52B | 0.2667 | 0.5598 | 0.1732 | 0.063* | |
H53B | 0.5237 | 0.5321 | 0.1750 | 0.063* | |
C6B | 0.7551 (11) | 0.5865 (2) | 0.13178 (14) | 0.0364 (19) | |
H61B | 0.7033 | 0.5656 | 0.1147 | 0.055* | |
H62B | 0.8748 | 0.5681 | 0.1439 | 0.055* | |
H63B | 0.8275 | 0.6177 | 0.1241 | 0.055* | |
C7B | 0.7386 (8) | 0.68052 (15) | 0.16885 (13) | 0.0184 (15) | |
O1C | 0.5635 (7) | 0.63502 (15) | 0.38021 (9) | 0.0284 (11) | |
O2C | 0.5706 (8) | 0.68407 (14) | 0.30779 (10) | 0.0256 (11) | |
O3C | 0.9152 (7) | 0.64068 (15) | 0.30723 (9) | 0.0262 (11) | |
N1C | 0.1991 (10) | 0.68115 (17) | 0.40870 (9) | 0.0191 (12) | |
H1C | 0.0914 | 0.6702 | 0.4229 | 0.029* | |
H2C | 0.1874 | 0.7152 | 0.4068 | 0.029* | |
H3C | 0.3519 | 0.6728 | 0.4146 | 0.029* | |
N2C | 0.3436 (7) | 0.61148 (16) | 0.33923 (8) | 0.0177 (12) | |
H4C | 0.1971 | 0.6053 | 0.3323 | 0.021* | |
C1C | 0.1449 (9) | 0.6571 (2) | 0.37919 (11) | 0.0292 (17) | |
H11C | 0.0816 | 0.6826 | 0.3649 | 0.035* | |
H12C | 0.0193 | 0.6310 | 0.3820 | 0.035* | |
C2C | 0.3708 (8) | 0.63367 (19) | 0.36633 (9) | 0.0154 (14) | |
C3C | 0.5534 (8) | 0.59740 (15) | 0.32105 (9) | 0.0194 (15) | |
H31C | 0.6621 | 0.5759 | 0.3337 | 0.023* | |
C4C | 0.4684 (10) | 0.56650 (18) | 0.29373 (11) | 0.0266 (17) | |
H41C | 0.3518 | 0.5877 | 0.2820 | 0.032* | |
C5C | 0.3346 (12) | 0.5197 (2) | 0.30412 (14) | 0.0339 (18) | |
H51C | 0.2010 | 0.5293 | 0.3175 | 0.051* | |
H52C | 0.4464 | 0.4976 | 0.3151 | 0.051* | |
H53C | 0.2700 | 0.5019 | 0.2864 | 0.051* | |
C6C | 0.6753 (12) | 0.5525 (3) | 0.27258 (13) | 0.0384 (19) | |
H61C | 0.7588 | 0.5831 | 0.2660 | 0.058* | |
H62C | 0.6108 | 0.5348 | 0.2549 | 0.058* | |
H63C | 0.7897 | 0.5306 | 0.2833 | 0.058* | |
C7C | 0.6940 (8) | 0.64488 (16) | 0.31159 (12) | 0.0198 (15) | |
O1D | 0.6089 (7) | 0.68049 (15) | 0.52337 (9) | 0.0242 (11) | |
O2D | 0.6016 (7) | 0.68173 (13) | 0.44650 (9) | 0.0219 (10) | |
O3D | 0.9414 (6) | 0.64067 (14) | 0.45755 (9) | 0.0185 (10) | |
N1D | 0.2257 (9) | 0.72095 (17) | 0.55292 (9) | 0.0155 (12) | |
H1D | 0.1221 | 0.7055 | 0.5660 | 0.023* | |
H2D | 0.1965 | 0.7546 | 0.5529 | 0.023* | |
H3D | 0.3809 | 0.7152 | 0.5589 | 0.023* | |
N2D | 0.3688 (8) | 0.63394 (15) | 0.49262 (9) | 0.0199 (12) | |
H4D | 0.2196 | 0.6250 | 0.4882 | 0.024* | |
C1D | 0.1889 (9) | 0.7006 (2) | 0.52198 (11) | 0.0189 (15) | |
H11D | 0.1643 | 0.7286 | 0.5075 | 0.023* | |
H12D | 0.0432 | 0.6789 | 0.5216 | 0.023* | |
C2D | 0.4084 (8) | 0.67038 (18) | 0.51292 (11) | 0.0183 (14) | |
C3D | 0.5715 (8) | 0.60896 (13) | 0.47787 (9) | 0.0137 (13) | |
H31D | 0.6786 | 0.5942 | 0.4938 | 0.016* | |
C4D | 0.4742 (9) | 0.56617 (15) | 0.45784 (10) | 0.0151 (14) | |
H41D | 0.3579 | 0.5811 | 0.4430 | 0.018* | |
C5D | 0.3380 (11) | 0.52756 (19) | 0.47671 (13) | 0.0288 (17) | |
H51D | 0.2761 | 0.5009 | 0.4634 | 0.043* | |
H52D | 0.2024 | 0.5440 | 0.4871 | 0.043* | |
H53D | 0.4477 | 0.5129 | 0.4918 | 0.043* | |
C6D | 0.6770 (11) | 0.5411 (2) | 0.44002 (12) | 0.0254 (16) | |
H61D | 0.6093 | 0.5144 | 0.4272 | 0.038* | |
H62D | 0.7946 | 0.5265 | 0.4541 | 0.038* | |
H63D | 0.7576 | 0.5662 | 0.4272 | 0.038* | |
C7D | 0.7193 (7) | 0.64737 (16) | 0.45933 (11) | 0.0135 (14) | |
O1E | 0.6001 (8) | 0.68919 (17) | 0.66735 (10) | 0.0318 (12) | |
O2E | 0.6311 (7) | 0.71674 (12) | 0.59262 (9) | 0.0221 (11) | |
O3E | 0.9679 (6) | 0.67145 (14) | 0.59615 (10) | 0.0237 (11) | |
N1E | 0.1973 (10) | 0.71915 (19) | 0.69669 (9) | 0.0243 (14) | |
H1E | 0.0843 | 0.7036 | 0.7084 | 0.036* | |
H2E | 0.1751 | 0.7530 | 0.6975 | 0.036* | |
H3E | 0.3479 | 0.7114 | 0.7036 | 0.036* | |
N2E | 0.3910 (7) | 0.65149 (15) | 0.62945 (9) | 0.0202 (12) | |
H4E | 0.2467 | 0.6429 | 0.6228 | 0.024* | |
C1E | 0.1725 (9) | 0.7019 (3) | 0.66506 (12) | 0.0334 (18) | |
H11E | 0.1238 | 0.7305 | 0.6520 | 0.040* | |
H12E | 0.0451 | 0.6758 | 0.6638 | 0.040* | |
C2E | 0.4093 (8) | 0.6806 (2) | 0.65404 (10) | 0.0221 (15) | |
C3E | 0.6045 (8) | 0.63381 (14) | 0.61355 (10) | 0.0181 (14) | |
H31E | 0.7121 | 0.6168 | 0.6286 | 0.022* | |
C4E | 0.5274 (9) | 0.59464 (16) | 0.59005 (11) | 0.0216 (15) | |
H41E | 0.4027 | 0.6107 | 0.5767 | 0.026* | |
C5E | 0.4101 (13) | 0.5494 (2) | 0.60510 (14) | 0.0383 (19) | |
H51E | 0.2773 | 0.5607 | 0.6182 | 0.057* | |
H52E | 0.5308 | 0.5316 | 0.6173 | 0.057* | |
H53E | 0.3465 | 0.5267 | 0.5895 | 0.057* | |
C6E | 0.7344 (11) | 0.5778 (2) | 0.56980 (13) | 0.0345 (18) | |
H61E | 0.8081 | 0.6073 | 0.5601 | 0.052* | |
H62E | 0.6725 | 0.5550 | 0.5542 | 0.052* | |
H63E | 0.8562 | 0.5603 | 0.5820 | 0.052* | |
C7E | 0.7460 (7) | 0.67782 (16) | 0.59960 (12) | 0.0176 (15) | |
O1F | 0.5668 (7) | 0.63960 (17) | 0.80719 (9) | 0.0295 (12) | |
O2F | 0.5873 (8) | 0.70117 (14) | 0.73716 (9) | 0.0278 (11) | |
O3F | 0.9299 (7) | 0.65752 (16) | 0.73459 (10) | 0.0307 (12) | |
N1F | 0.1901 (10) | 0.67809 (17) | 0.83745 (9) | 0.0177 (12) | |
H1F | 0.0838 | 0.6653 | 0.8512 | 0.026* | |
H2F | 0.1723 | 0.7121 | 0.8365 | 0.026* | |
H3F | 0.3440 | 0.6706 | 0.8433 | 0.026* | |
N2F | 0.3564 (8) | 0.62346 (17) | 0.76419 (8) | 0.0246 (13) | |
H4F | 0.2116 | 0.6196 | 0.7562 | 0.030* | |
C1F | 0.1421 (9) | 0.6559 (3) | 0.80735 (11) | 0.0270 (17) | |
H11F | 0.0616 | 0.6811 | 0.7942 | 0.032* | |
H12F | 0.0322 | 0.6267 | 0.8095 | 0.032* | |
C2F | 0.3760 (8) | 0.6393 (2) | 0.79288 (9) | 0.0223 (15) | |
C3F | 0.5689 (9) | 0.61250 (15) | 0.74594 (9) | 0.0223 (15) | |
H31F | 0.6776 | 0.5898 | 0.7578 | 0.027* | |
C4F | 0.4914 (10) | 0.58489 (18) | 0.71692 (10) | 0.0237 (16) | |
H41F | 0.3786 | 0.6075 | 0.7056 | 0.028* | |
C5F | 0.3552 (12) | 0.5369 (2) | 0.72437 (14) | 0.0359 (19) | |
H51F | 0.3079 | 0.5201 | 0.7055 | 0.054* | |
H52F | 0.2101 | 0.5452 | 0.7362 | 0.054* | |
H53F | 0.4597 | 0.5146 | 0.7363 | 0.054* | |
C6F | 0.7050 (12) | 0.5735 (2) | 0.69633 (13) | 0.0378 (19) | |
H61F | 0.6476 | 0.5562 | 0.6781 | 0.057* | |
H62F | 0.8204 | 0.5519 | 0.7071 | 0.057* | |
H63F | 0.7849 | 0.6050 | 0.6906 | 0.057* | |
C7F | 0.7081 (8) | 0.66133 (16) | 0.73877 (13) | 0.0215 (16) | |
O1G | 0.5927 (8) | 0.65189 (18) | 0.95235 (10) | 0.0383 (13) | |
O2G | 0.5846 (7) | 0.67127 (12) | 0.87620 (9) | 0.0208 (10) | |
O3G | 0.9293 (6) | 0.62970 (14) | 0.88348 (9) | 0.0223 (10) | |
N1G | 0.2217 (10) | 0.6979 (2) | 0.98004 (10) | 0.0289 (14) | |
H1G | 0.1280 | 0.6826 | 0.9943 | 0.043* | |
H2G | 0.1848 | 0.7312 | 0.9792 | 0.043* | |
H3G | 0.3806 | 0.6941 | 0.9850 | 0.043* | |
N2G | 0.3571 (8) | 0.61279 (16) | 0.91741 (9) | 0.0237 (13) | |
H4G | 0.2085 | 0.6042 | 0.9124 | 0.028* | |
C1G | 0.1755 (10) | 0.6747 (3) | 0.95012 (13) | 0.0354 (19) | |
H11G | 0.1399 | 0.7012 | 0.9350 | 0.043* | |
H12G | 0.0333 | 0.6521 | 0.9514 | 0.043* | |
C2G | 0.3946 (9) | 0.6451 (2) | 0.94031 (11) | 0.0298 (17) | |
C3G | 0.5620 (8) | 0.59193 (14) | 0.90086 (10) | 0.0183 (14) | |
H31G | 0.6695 | 0.5736 | 0.9154 | 0.022* | |
C4G | 0.4703 (9) | 0.55484 (16) | 0.87672 (11) | 0.0221 (15) | |
H41G | 0.3565 | 0.5735 | 0.8631 | 0.027* | |
C5G | 0.3311 (11) | 0.51202 (19) | 0.89109 (14) | 0.0317 (17) | |
H51G | 0.2744 | 0.4890 | 0.8752 | 0.048* | |
H52G | 0.1917 | 0.5255 | 0.9022 | 0.048* | |
H53G | 0.4369 | 0.4938 | 0.9051 | 0.048* | |
C6G | 0.6773 (11) | 0.5351 (2) | 0.85726 (13) | 0.0319 (17) | |
H61G | 0.7664 | 0.5635 | 0.8485 | 0.048* | |
H62G | 0.6119 | 0.5141 | 0.8409 | 0.048* | |
H63G | 0.7869 | 0.5149 | 0.8698 | 0.048* | |
C7G | 0.7070 (7) | 0.63495 (16) | 0.88592 (12) | 0.0174 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.019 (2) | 0.030 (2) | 0.027 (2) | −0.003 (2) | −0.001 (2) | −0.0059 (19) |
O2A | 0.031 (3) | 0.048 (3) | 0.021 (2) | 0.002 (2) | 0.000 (2) | 0.005 (2) |
O3A | 0.023 (3) | 0.053 (3) | 0.023 (2) | −0.002 (2) | 0.002 (2) | −0.007 (2) |
N1A | 0.019 (3) | 0.019 (2) | 0.020 (3) | −0.003 (2) | 0.000 (2) | −0.001 (2) |
N2A | 0.016 (3) | 0.030 (3) | 0.023 (3) | −0.002 (2) | −0.001 (2) | −0.012 (2) |
C1A | 0.016 (3) | 0.027 (3) | 0.019 (3) | −0.004 (3) | 0.000 (3) | −0.004 (2) |
C2A | 0.020 (3) | 0.020 (3) | 0.015 (3) | −0.003 (3) | 0.000 (3) | −0.001 (2) |
C3A | 0.022 (3) | 0.028 (3) | 0.021 (3) | 0.006 (3) | −0.002 (3) | −0.009 (2) |
C4A | 0.027 (3) | 0.033 (3) | 0.030 (3) | −0.002 (3) | 0.003 (3) | −0.009 (3) |
C5A | 0.040 (4) | 0.030 (3) | 0.036 (3) | −0.006 (3) | −0.002 (3) | −0.015 (3) |
C6A | 0.047 (4) | 0.054 (4) | 0.042 (4) | 0.008 (3) | 0.006 (3) | −0.018 (3) |
C7A | 0.024 (4) | 0.041 (3) | 0.018 (3) | 0.000 (3) | −0.004 (3) | −0.006 (3) |
O1B | 0.027 (3) | 0.069 (3) | 0.027 (2) | 0.004 (3) | 0.002 (2) | 0.000 (2) |
O2B | 0.022 (3) | 0.022 (2) | 0.022 (2) | −0.001 (2) | 0.001 (2) | 0.0002 (18) |
O3B | 0.021 (3) | 0.027 (2) | 0.021 (2) | −0.001 (2) | −0.001 (2) | 0.0006 (19) |
N1B | 0.020 (3) | 0.043 (3) | 0.018 (3) | 0.001 (3) | 0.002 (2) | 0.008 (2) |
N2B | 0.021 (3) | 0.029 (3) | 0.021 (3) | −0.002 (2) | 0.002 (2) | 0.002 (2) |
C1B | 0.033 (4) | 0.052 (4) | 0.022 (3) | 0.002 (3) | 0.000 (3) | −0.004 (3) |
C2B | 0.022 (3) | 0.036 (3) | 0.017 (3) | 0.003 (3) | 0.001 (3) | 0.009 (3) |
C3B | 0.021 (3) | 0.024 (3) | 0.015 (3) | 0.000 (3) | 0.002 (3) | 0.005 (2) |
C4B | 0.029 (3) | 0.019 (3) | 0.018 (3) | 0.000 (3) | −0.003 (3) | −0.005 (2) |
C5B | 0.046 (4) | 0.033 (3) | 0.047 (4) | −0.008 (3) | −0.004 (3) | 0.000 (3) |
C6B | 0.040 (4) | 0.035 (3) | 0.034 (3) | −0.004 (3) | 0.006 (3) | −0.003 (3) |
C7B | 0.017 (3) | 0.025 (3) | 0.013 (3) | 0.003 (3) | −0.002 (2) | −0.003 (2) |
O1C | 0.024 (3) | 0.035 (2) | 0.026 (2) | −0.001 (2) | −0.007 (2) | −0.012 (2) |
O2C | 0.024 (3) | 0.033 (2) | 0.020 (2) | −0.001 (2) | −0.002 (2) | 0.0057 (19) |
O3C | 0.023 (3) | 0.037 (2) | 0.019 (2) | −0.003 (2) | −0.002 (2) | −0.0003 (19) |
N1C | 0.021 (3) | 0.019 (2) | 0.018 (3) | 0.000 (2) | −0.002 (2) | 0.001 (2) |
N2C | 0.016 (2) | 0.023 (2) | 0.014 (2) | −0.0025 (19) | −0.0015 (19) | −0.0031 (18) |
C1C | 0.028 (4) | 0.040 (3) | 0.019 (3) | −0.001 (3) | 0.001 (3) | −0.007 (3) |
C2C | 0.014 (3) | 0.018 (3) | 0.014 (3) | −0.004 (2) | 0.000 (2) | −0.001 (2) |
C3C | 0.018 (3) | 0.030 (3) | 0.011 (3) | 0.002 (3) | −0.001 (3) | −0.003 (2) |
C4C | 0.026 (3) | 0.038 (3) | 0.016 (3) | −0.008 (3) | 0.002 (3) | −0.012 (3) |
C5C | 0.037 (4) | 0.041 (3) | 0.023 (3) | −0.007 (3) | 0.001 (3) | −0.018 (3) |
C6C | 0.039 (4) | 0.050 (4) | 0.026 (3) | −0.005 (3) | 0.010 (3) | −0.018 (3) |
C7C | 0.019 (2) | 0.027 (2) | 0.014 (2) | −0.003 (2) | −0.003 (2) | −0.0007 (19) |
O1D | 0.016 (2) | 0.031 (2) | 0.025 (2) | 0.000 (2) | −0.002 (2) | −0.0079 (19) |
O2D | 0.024 (2) | 0.020 (2) | 0.021 (2) | 0.000 (2) | −0.007 (2) | 0.0001 (17) |
O3D | 0.020 (2) | 0.022 (2) | 0.014 (2) | −0.0032 (19) | 0.0026 (18) | 0.0019 (17) |
N1D | 0.017 (3) | 0.018 (2) | 0.012 (2) | 0.001 (2) | 0.002 (2) | −0.001 (2) |
N2D | 0.020 (2) | 0.026 (2) | 0.014 (2) | 0.0020 (19) | 0.0010 (18) | −0.0055 (17) |
C1D | 0.021 (3) | 0.021 (3) | 0.015 (3) | 0.004 (3) | −0.003 (3) | 0.001 (2) |
C2D | 0.018 (3) | 0.024 (2) | 0.013 (2) | 0.004 (2) | 0.002 (2) | 0.000 (2) |
C3D | 0.014 (2) | 0.016 (2) | 0.011 (2) | 0.001 (2) | 0.0001 (19) | −0.0033 (18) |
C4D | 0.016 (2) | 0.018 (2) | 0.011 (2) | 0.0000 (18) | −0.0029 (18) | 0.0005 (17) |
C5D | 0.029 (3) | 0.024 (3) | 0.033 (3) | −0.001 (3) | 0.001 (3) | 0.003 (3) |
C6D | 0.028 (3) | 0.026 (3) | 0.023 (3) | −0.001 (3) | 0.005 (3) | −0.002 (3) |
C7D | 0.015 (2) | 0.015 (2) | 0.010 (2) | −0.0029 (18) | −0.0007 (18) | −0.0014 (17) |
O1E | 0.023 (3) | 0.046 (3) | 0.027 (2) | 0.004 (2) | −0.003 (2) | −0.005 (2) |
O2E | 0.027 (3) | 0.018 (2) | 0.022 (2) | 0.004 (2) | −0.004 (2) | 0.0014 (17) |
O3E | 0.020 (2) | 0.034 (2) | 0.018 (2) | 0.0015 (19) | 0.0018 (19) | 0.0086 (19) |
N1E | 0.020 (3) | 0.032 (3) | 0.021 (3) | 0.005 (2) | 0.005 (2) | −0.002 (2) |
N2E | 0.018 (3) | 0.029 (2) | 0.014 (2) | −0.002 (2) | −0.001 (2) | 0.002 (2) |
C1E | 0.030 (4) | 0.043 (3) | 0.027 (3) | 0.005 (3) | 0.001 (3) | −0.007 (3) |
C2E | 0.019 (3) | 0.028 (3) | 0.020 (3) | 0.003 (3) | −0.003 (3) | 0.003 (3) |
C3E | 0.021 (3) | 0.019 (3) | 0.014 (3) | 0.001 (3) | −0.005 (3) | 0.001 (2) |
C4E | 0.024 (3) | 0.019 (3) | 0.021 (3) | 0.000 (3) | −0.005 (3) | −0.001 (2) |
C5E | 0.048 (4) | 0.033 (3) | 0.034 (3) | −0.007 (3) | −0.003 (3) | −0.002 (3) |
C6E | 0.044 (4) | 0.033 (3) | 0.027 (3) | 0.007 (3) | −0.001 (3) | −0.008 (3) |
C7E | 0.019 (3) | 0.021 (2) | 0.013 (2) | 0.000 (2) | −0.002 (2) | 0.002 (2) |
O1F | 0.023 (3) | 0.047 (3) | 0.018 (2) | 0.010 (2) | −0.003 (2) | −0.002 (2) |
O2F | 0.026 (3) | 0.038 (2) | 0.020 (2) | −0.001 (2) | 0.001 (2) | −0.0038 (19) |
O3F | 0.024 (3) | 0.045 (3) | 0.022 (2) | 0.003 (2) | 0.001 (2) | 0.005 (2) |
N1F | 0.016 (2) | 0.025 (2) | 0.012 (2) | 0.0011 (19) | 0.0017 (19) | 0.0013 (18) |
N2F | 0.024 (2) | 0.032 (2) | 0.018 (2) | 0.001 (2) | 0.000 (2) | −0.0019 (19) |
C1F | 0.026 (4) | 0.031 (3) | 0.024 (3) | 0.000 (3) | −0.002 (3) | −0.011 (3) |
C2F | 0.019 (3) | 0.031 (3) | 0.016 (3) | 0.002 (3) | 0.000 (3) | 0.000 (3) |
C3F | 0.023 (3) | 0.030 (3) | 0.013 (3) | 0.005 (3) | 0.000 (3) | 0.002 (2) |
C4F | 0.028 (3) | 0.033 (3) | 0.010 (3) | 0.008 (3) | −0.002 (3) | −0.001 (3) |
C5F | 0.046 (4) | 0.035 (3) | 0.027 (3) | −0.002 (3) | −0.001 (3) | 0.001 (3) |
C6F | 0.042 (4) | 0.043 (3) | 0.029 (3) | 0.010 (3) | 0.003 (3) | −0.004 (3) |
C7F | 0.018 (3) | 0.030 (3) | 0.016 (2) | 0.004 (2) | −0.003 (2) | −0.003 (2) |
O1G | 0.027 (3) | 0.060 (3) | 0.028 (2) | 0.006 (2) | −0.006 (2) | −0.012 (2) |
O2G | 0.024 (2) | 0.0181 (19) | 0.021 (2) | 0.0020 (19) | −0.004 (2) | 0.0010 (17) |
O3G | 0.017 (2) | 0.033 (2) | 0.017 (2) | 0.0005 (19) | −0.0003 (19) | 0.0023 (18) |
N1G | 0.022 (3) | 0.049 (3) | 0.015 (3) | 0.005 (3) | −0.001 (2) | −0.001 (2) |
N2G | 0.016 (3) | 0.037 (3) | 0.018 (2) | 0.000 (2) | −0.002 (2) | 0.000 (2) |
C1G | 0.036 (4) | 0.046 (4) | 0.024 (3) | 0.008 (3) | −0.003 (3) | −0.002 (3) |
C2G | 0.024 (3) | 0.048 (3) | 0.018 (3) | 0.000 (3) | 0.001 (3) | 0.001 (3) |
C3G | 0.018 (3) | 0.021 (3) | 0.016 (3) | −0.002 (3) | −0.003 (3) | 0.006 (2) |
C4G | 0.023 (3) | 0.017 (3) | 0.026 (3) | 0.000 (2) | −0.003 (3) | −0.003 (3) |
C5G | 0.033 (4) | 0.030 (3) | 0.032 (3) | −0.006 (3) | −0.007 (3) | 0.009 (3) |
C6G | 0.032 (4) | 0.035 (3) | 0.028 (3) | −0.001 (3) | 0.000 (3) | −0.011 (3) |
C7G | 0.018 (3) | 0.020 (2) | 0.014 (2) | −0.002 (2) | 0.000 (2) | −0.003 (2) |
O1A—C2A | 1.230 (4) | C3D—C4D | 1.537 (4) |
O2A—C7A | 1.254 (4) | C3D—C7D | 1.542 (4) |
O3A—C7A | 1.247 (4) | C3D—H31D | 1.0000 |
N1A—C1A | 1.480 (5) | C4D—C6D | 1.522 (5) |
N1A—H1A | 0.9100 | C4D—C5D | 1.520 (5) |
N1A—H2A | 0.9100 | C4D—H41D | 1.0000 |
N1A—H3A | 0.9100 | C5D—H51D | 0.9800 |
N2A—C2A | 1.335 (4) | C5D—H52D | 0.9800 |
N2A—C3A | 1.452 (4) | C5D—H53D | 0.9800 |
N2A—H4A | 0.8800 | C6D—H61D | 0.9800 |
C1A—C2A | 1.506 (4) | C6D—H62D | 0.9800 |
C1A—H11A | 0.9900 | C6D—H63D | 0.9800 |
C1A—H12A | 0.9900 | O1E—C2E | 1.228 (4) |
C3A—C7A | 1.535 (4) | O2E—C7E | 1.252 (4) |
C3A—C4A | 1.534 (5) | O3E—C7E | 1.246 (4) |
C3A—H31A | 1.0000 | N1E—C1E | 1.475 (5) |
C4A—C6A | 1.517 (5) | N1E—H1E | 0.9100 |
C4A—C5A | 1.517 (5) | N1E—H2E | 0.9100 |
C4A—H41A | 1.0000 | N1E—H3E | 0.9100 |
C5A—H51A | 0.9800 | N2E—C2E | 1.336 (4) |
C5A—H52A | 0.9800 | N2E—C3E | 1.450 (4) |
C5A—H53A | 0.9800 | N2E—H4E | 0.8800 |
C6A—H61A | 0.9800 | C1E—C2E | 1.506 (5) |
C6A—H62A | 0.9800 | C1E—H11E | 0.9900 |
C6A—H63A | 0.9800 | C1E—H12E | 0.9900 |
O1B—C2B | 1.228 (4) | C3E—C4E | 1.529 (4) |
O2B—C7B | 1.256 (4) | C3E—C7E | 1.536 (4) |
O3B—C7B | 1.245 (4) | C3E—H31E | 1.0000 |
N1B—C1B | 1.476 (5) | C4E—C6E | 1.518 (5) |
N1B—H1B | 0.9100 | C4E—C5E | 1.519 (5) |
N1B—H2B | 0.9100 | C4E—H41E | 1.0000 |
N1B—H3B | 0.9100 | C5E—H51E | 0.9800 |
N2B—C2B | 1.337 (4) | C5E—H52E | 0.9800 |
N2B—C3B | 1.452 (4) | C5E—H53E | 0.9800 |
N2B—H4B | 0.8800 | C6E—H61E | 0.9800 |
C1B—C2B | 1.507 (5) | C6E—H62E | 0.9800 |
C1B—H11B | 0.9900 | C6E—H63E | 0.9800 |
C1B—H12B | 0.9900 | O1F—C2F | 1.229 (4) |
C3B—C7B | 1.536 (4) | O2F—C7F | 1.254 (4) |
C3B—C4B | 1.532 (4) | O3F—C7F | 1.243 (4) |
C3B—H31B | 1.0000 | N1F—C1F | 1.476 (5) |
C4B—C6B | 1.519 (5) | N1F—H1F | 0.9100 |
C4B—C5B | 1.518 (5) | N1F—H2F | 0.9100 |
C4B—H41B | 1.0000 | N1F—H3F | 0.9100 |
C5B—H51B | 0.9800 | N2F—C2F | 1.338 (4) |
C5B—H52B | 0.9800 | N2F—C3F | 1.453 (4) |
C5B—H53B | 0.9800 | N2F—H4F | 0.8800 |
C6B—H61B | 0.9800 | C1F—C2F | 1.508 (5) |
C6B—H62B | 0.9800 | C1F—H11F | 0.9900 |
C6B—H63B | 0.9800 | C1F—H12F | 0.9900 |
O1C—C2C | 1.228 (4) | C3F—C4F | 1.536 (4) |
O2C—C7C | 1.256 (4) | C3F—C7F | 1.542 (4) |
O3C—C7C | 1.242 (4) | C3F—H31F | 1.0000 |
N1C—C1C | 1.480 (5) | C4F—C6F | 1.519 (5) |
N1C—H1C | 0.9100 | C4F—C5F | 1.516 (5) |
N1C—H2C | 0.9100 | C4F—H41F | 1.0000 |
N1C—H3C | 0.9100 | C5F—H51F | 0.9800 |
N2C—C2C | 1.341 (4) | C5F—H52F | 0.9800 |
N2C—C3C | 1.458 (4) | C5F—H53F | 0.9800 |
N2C—H4C | 0.8800 | C6F—H61F | 0.9800 |
C1C—C2C | 1.506 (5) | C6F—H62F | 0.9800 |
C1C—H11C | 0.9900 | C6F—H63F | 0.9800 |
C1C—H12C | 0.9900 | O1G—C2G | 1.230 (4) |
C3C—C4C | 1.531 (4) | O2G—C7G | 1.254 (4) |
C3C—C7C | 1.539 (4) | O3G—C7G | 1.241 (4) |
C3C—H31C | 1.0000 | N1G—C1G | 1.479 (5) |
C4C—C6C | 1.521 (5) | N1G—H1G | 0.9100 |
C4C—C5C | 1.519 (5) | N1G—H2G | 0.9100 |
C4C—H41C | 1.0000 | N1G—H3G | 0.9100 |
C5C—H51C | 0.9800 | N2G—C2G | 1.341 (4) |
C5C—H52C | 0.9800 | N2G—C3G | 1.457 (4) |
C5C—H53C | 0.9800 | N2G—H4G | 0.8800 |
C6C—H61C | 0.9800 | C1G—C2G | 1.507 (5) |
C6C—H62C | 0.9800 | C1G—H11G | 0.9900 |
C6C—H63C | 0.9800 | C1G—H12G | 0.9900 |
O1D—C2D | 1.229 (4) | C3G—C4G | 1.537 (5) |
O2D—C7D | 1.256 (4) | C3G—C7G | 1.544 (4) |
O3D—C7D | 1.242 (4) | C3G—H31G | 1.0000 |
N1D—C1D | 1.481 (5) | C4G—C5G | 1.512 (5) |
N1D—H1D | 0.9100 | C4G—C6G | 1.524 (5) |
N1D—H2D | 0.9100 | C4G—H41G | 1.0000 |
N1D—H3D | 0.9100 | C5G—H51G | 0.9800 |
N2D—C2D | 1.337 (4) | C5G—H52G | 0.9800 |
N2D—C3D | 1.455 (4) | C5G—H53G | 0.9800 |
N2D—H4D | 0.8800 | C6G—H61G | 0.9800 |
C1D—C2D | 1.508 (5) | C6G—H62G | 0.9800 |
C1D—H11D | 0.9900 | C6G—H63G | 0.9800 |
C1D—H12D | 0.9900 | ||
C1A—N1A—H1A | 109.5 | C7D—C3D—H31D | 108.7 |
C1A—N1A—H2A | 109.5 | C6D—C4D—C5D | 110.5 (4) |
H1A—N1A—H2A | 109.5 | C6D—C4D—C3D | 111.3 (4) |
C1A—N1A—H3A | 109.5 | C5D—C4D—C3D | 111.0 (3) |
H1A—N1A—H3A | 109.5 | C6D—C4D—H41D | 107.9 |
H2A—N1A—H3A | 109.5 | C5D—C4D—H41D | 107.9 |
C2A—N2A—C3A | 121.0 (4) | C3D—C4D—H41D | 107.9 |
C2A—N2A—H4A | 119.5 | C4D—C5D—H51D | 109.5 |
C3A—N2A—H4A | 119.5 | C4D—C5D—H52D | 109.5 |
N1A—C1A—C2A | 109.4 (4) | H51D—C5D—H52D | 109.5 |
N1A—C1A—H11A | 109.8 | C4D—C5D—H53D | 109.5 |
C2A—C1A—H11A | 109.8 | H51D—C5D—H53D | 109.5 |
N1A—C1A—H12A | 109.8 | H52D—C5D—H53D | 109.5 |
C2A—C1A—H12A | 109.8 | C4D—C6D—H61D | 109.5 |
H11A—C1A—H12A | 108.2 | C4D—C6D—H62D | 109.5 |
O1A—C2A—N2A | 123.6 (4) | H61D—C6D—H62D | 109.5 |
O1A—C2A—C1A | 120.8 (3) | C4D—C6D—H63D | 109.5 |
N2A—C2A—C1A | 115.6 (4) | H61D—C6D—H63D | 109.5 |
N2A—C3A—C7A | 111.4 (3) | H62D—C6D—H63D | 109.5 |
N2A—C3A—C4A | 108.7 (3) | O3D—C7D—O2D | 126.0 (4) |
C7A—C3A—C4A | 112.5 (4) | O3D—C7D—C3D | 117.5 (4) |
N2A—C3A—H31A | 108.0 | O2D—C7D—C3D | 116.5 (3) |
C7A—C3A—H31A | 108.0 | C1E—N1E—H1E | 109.5 |
C4A—C3A—H31A | 108.0 | C1E—N1E—H2E | 109.5 |
C6A—C4A—C5A | 110.8 (4) | H1E—N1E—H2E | 109.5 |
C6A—C4A—C3A | 112.8 (4) | C1E—N1E—H3E | 109.5 |
C5A—C4A—C3A | 110.4 (4) | H1E—N1E—H3E | 109.5 |
C6A—C4A—H41A | 107.6 | H2E—N1E—H3E | 109.5 |
C5A—C4A—H41A | 107.6 | C2E—N2E—C3E | 121.3 (4) |
C3A—C4A—H41A | 107.6 | C2E—N2E—H4E | 119.4 |
C4A—C5A—H51A | 109.5 | C3E—N2E—H4E | 119.4 |
C4A—C5A—H52A | 109.5 | N1E—C1E—C2E | 110.0 (4) |
H51A—C5A—H52A | 109.5 | N1E—C1E—H11E | 109.7 |
C4A—C5A—H53A | 109.5 | C2E—C1E—H11E | 109.7 |
H51A—C5A—H53A | 109.5 | N1E—C1E—H12E | 109.7 |
H52A—C5A—H53A | 109.5 | C2E—C1E—H12E | 109.7 |
C4A—C6A—H61A | 109.5 | H11E—C1E—H12E | 108.2 |
C4A—C6A—H62A | 109.5 | O1E—C2E—N2E | 124.1 (4) |
H61A—C6A—H62A | 109.5 | O1E—C2E—C1E | 121.5 (4) |
C4A—C6A—H63A | 109.5 | N2E—C2E—C1E | 114.5 (4) |
H61A—C6A—H63A | 109.5 | N2E—C3E—C4E | 108.8 (3) |
H62A—C6A—H63A | 109.5 | N2E—C3E—C7E | 111.1 (3) |
O2A—C7A—O3A | 125.7 (4) | C4E—C3E—C7E | 112.9 (3) |
O2A—C7A—C3A | 117.3 (4) | N2E—C3E—H31E | 108.0 |
O3A—C7A—C3A | 117.0 (4) | C4E—C3E—H31E | 108.0 |
C1B—N1B—H1B | 109.5 | C7E—C3E—H31E | 108.0 |
C1B—N1B—H2B | 109.5 | C6E—C4E—C5E | 110.2 (4) |
H1B—N1B—H2B | 109.5 | C6E—C4E—C3E | 112.9 (4) |
C1B—N1B—H3B | 109.5 | C5E—C4E—C3E | 111.2 (4) |
H1B—N1B—H3B | 109.5 | C6E—C4E—H41E | 107.4 |
H2B—N1B—H3B | 109.5 | C5E—C4E—H41E | 107.4 |
C2B—N2B—C3B | 121.2 (4) | C3E—C4E—H41E | 107.4 |
C2B—N2B—H4B | 119.4 | C4E—C5E—H51E | 109.5 |
C3B—N2B—H4B | 119.4 | C4E—C5E—H52E | 109.5 |
N1B—C1B—C2B | 110.1 (4) | H51E—C5E—H52E | 109.5 |
N1B—C1B—H11B | 109.6 | C4E—C5E—H53E | 109.5 |
C2B—C1B—H11B | 109.6 | H51E—C5E—H53E | 109.5 |
N1B—C1B—H12B | 109.6 | H52E—C5E—H53E | 109.5 |
C2B—C1B—H12B | 109.6 | C4E—C6E—H61E | 109.5 |
H11B—C1B—H12B | 108.2 | C4E—C6E—H62E | 109.5 |
O1B—C2B—N2B | 124.3 (4) | H61E—C6E—H62E | 109.5 |
O1B—C2B—C1B | 120.9 (4) | C4E—C6E—H63E | 109.5 |
N2B—C2B—C1B | 114.7 (4) | H61E—C6E—H63E | 109.5 |
N2B—C3B—C7B | 110.9 (3) | H62E—C6E—H63E | 109.5 |
N2B—C3B—C4B | 109.4 (3) | O2E—C7E—O3E | 125.5 (4) |
C7B—C3B—C4B | 112.5 (3) | O2E—C7E—C3E | 118.0 (3) |
N2B—C3B—H31B | 108.0 | O3E—C7E—C3E | 116.5 (4) |
C7B—C3B—H31B | 108.0 | C1F—N1F—H1F | 109.5 |
C4B—C3B—H31B | 108.0 | C1F—N1F—H2F | 109.5 |
C6B—C4B—C5B | 110.2 (4) | H1F—N1F—H2F | 109.5 |
C6B—C4B—C3B | 112.8 (4) | C1F—N1F—H3F | 109.5 |
C5B—C4B—C3B | 111.0 (4) | H1F—N1F—H3F | 109.5 |
C6B—C4B—H41B | 107.5 | H2F—N1F—H3F | 109.5 |
C5B—C4B—H41B | 107.5 | C2F—N2F—C3F | 121.4 (4) |
C3B—C4B—H41B | 107.5 | C2F—N2F—H4F | 119.3 |
C4B—C5B—H51B | 109.5 | C3F—N2F—H4F | 119.3 |
C4B—C5B—H52B | 109.5 | N1F—C1F—C2F | 110.1 (4) |
H51B—C5B—H52B | 109.5 | N1F—C1F—H11F | 109.6 |
C4B—C5B—H53B | 109.5 | C2F—C1F—H11F | 109.6 |
H51B—C5B—H53B | 109.5 | N1F—C1F—H12F | 109.6 |
H52B—C5B—H53B | 109.5 | C2F—C1F—H12F | 109.6 |
C4B—C6B—H61B | 109.5 | H11F—C1F—H12F | 108.2 |
C4B—C6B—H62B | 109.5 | O1F—C2F—N2F | 123.9 (4) |
H61B—C6B—H62B | 109.5 | O1F—C2F—C1F | 121.1 (3) |
C4B—C6B—H63B | 109.5 | N2F—C2F—C1F | 115.0 (4) |
H61B—C6B—H63B | 109.5 | N2F—C3F—C4F | 109.4 (3) |
H62B—C6B—H63B | 109.5 | N2F—C3F—C7F | 110.3 (3) |
O2B—C7B—O3B | 125.4 (4) | C4F—C3F—C7F | 111.7 (3) |
O2B—C7B—C3B | 117.6 (3) | N2F—C3F—H31F | 108.4 |
O3B—C7B—C3B | 117.0 (4) | C4F—C3F—H31F | 108.4 |
C1C—N1C—H1C | 109.5 | C7F—C3F—H31F | 108.4 |
C1C—N1C—H2C | 109.5 | C6F—C4F—C5F | 110.3 (4) |
H1C—N1C—H2C | 109.5 | C6F—C4F—C3F | 112.1 (4) |
C1C—N1C—H3C | 109.5 | C5F—C4F—C3F | 111.1 (4) |
H1C—N1C—H3C | 109.5 | C6F—C4F—H41F | 107.7 |
H2C—N1C—H3C | 109.5 | C5F—C4F—H41F | 107.7 |
C2C—N2C—C3C | 120.9 (4) | C3F—C4F—H41F | 107.7 |
C2C—N2C—H4C | 119.5 | C4F—C5F—H51F | 109.5 |
C3C—N2C—H4C | 119.5 | C4F—C5F—H52F | 109.5 |
N1C—C1C—C2C | 110.0 (4) | H51F—C5F—H52F | 109.5 |
N1C—C1C—H11C | 109.7 | C4F—C5F—H53F | 109.5 |
C2C—C1C—H11C | 109.7 | H51F—C5F—H53F | 109.5 |
N1C—C1C—H12C | 109.7 | H52F—C5F—H53F | 109.5 |
C2C—C1C—H12C | 109.7 | C4F—C6F—H61F | 109.5 |
H11C—C1C—H12C | 108.2 | C4F—C6F—H62F | 109.5 |
O1C—C2C—N2C | 123.6 (4) | H61F—C6F—H62F | 109.5 |
O1C—C2C—C1C | 121.2 (3) | C4F—C6F—H63F | 109.5 |
N2C—C2C—C1C | 115.1 (3) | H61F—C6F—H63F | 109.5 |
N2C—C3C—C4C | 109.1 (3) | H62F—C6F—H63F | 109.5 |
N2C—C3C—C7C | 109.9 (3) | O2F—C7F—O3F | 125.8 (4) |
C4C—C3C—C7C | 112.4 (3) | O2F—C7F—C3F | 117.2 (4) |
N2C—C3C—H31C | 108.5 | O3F—C7F—C3F | 117.0 (4) |
C4C—C3C—H31C | 108.5 | C1G—N1G—H1G | 109.5 |
C7C—C3C—H31C | 108.5 | C1G—N1G—H2G | 109.5 |
C6C—C4C—C5C | 110.5 (4) | H1G—N1G—H2G | 109.5 |
C6C—C4C—C3C | 112.5 (4) | C1G—N1G—H3G | 109.5 |
C5C—C4C—C3C | 110.6 (4) | H1G—N1G—H3G | 109.5 |
C6C—C4C—H41C | 107.7 | H2G—N1G—H3G | 109.5 |
C5C—C4C—H41C | 107.7 | C2G—N2G—C3G | 120.0 (4) |
C3C—C4C—H41C | 107.7 | C2G—N2G—H4G | 120.0 |
C4C—C5C—H51C | 109.5 | C3G—N2G—H4G | 120.0 |
C4C—C5C—H52C | 109.5 | N1G—C1G—C2G | 109.6 (4) |
H51C—C5C—H52C | 109.5 | N1G—C1G—H11G | 109.7 |
C4C—C5C—H53C | 109.5 | C2G—C1G—H11G | 109.7 |
H51C—C5C—H53C | 109.5 | N1G—C1G—H12G | 109.7 |
H52C—C5C—H53C | 109.5 | C2G—C1G—H12G | 109.7 |
C4C—C6C—H61C | 109.5 | H11G—C1G—H12G | 108.2 |
C4C—C6C—H62C | 109.5 | O1G—C2G—N2G | 123.8 (4) |
H61C—C6C—H62C | 109.5 | O1G—C2G—C1G | 120.9 (4) |
C4C—C6C—H63C | 109.5 | N2G—C2G—C1G | 115.2 (4) |
H61C—C6C—H63C | 109.5 | N2G—C3G—C4G | 109.6 (3) |
H62C—C6C—H63C | 109.5 | N2G—C3G—C7G | 109.6 (3) |
O3C—C7C—O2C | 126.0 (4) | C4G—C3G—C7G | 110.5 (3) |
O3C—C7C—C3C | 117.7 (4) | N2G—C3G—H31G | 109.0 |
O2C—C7C—C3C | 116.2 (4) | C4G—C3G—H31G | 109.0 |
C1D—N1D—H1D | 109.5 | C7G—C3G—H31G | 109.0 |
C1D—N1D—H2D | 109.5 | C5G—C4G—C6G | 111.0 (4) |
H1D—N1D—H2D | 109.5 | C5G—C4G—C3G | 111.1 (4) |
C1D—N1D—H3D | 109.5 | C6G—C4G—C3G | 111.3 (4) |
H1D—N1D—H3D | 109.5 | C5G—C4G—H41G | 107.7 |
H2D—N1D—H3D | 109.5 | C6G—C4G—H41G | 107.7 |
C2D—N2D—C3D | 120.3 (4) | C3G—C4G—H41G | 107.7 |
C2D—N2D—H4D | 119.9 | C4G—C5G—H51G | 109.5 |
C3D—N2D—H4D | 119.9 | C4G—C5G—H52G | 109.5 |
N1D—C1D—C2D | 109.2 (3) | H51G—C5G—H52G | 109.5 |
N1D—C1D—H11D | 109.8 | C4G—C5G—H53G | 109.5 |
C2D—C1D—H11D | 109.8 | H51G—C5G—H53G | 109.5 |
N1D—C1D—H12D | 109.8 | H52G—C5G—H53G | 109.5 |
C2D—C1D—H12D | 109.8 | C4G—C6G—H61G | 109.5 |
H11D—C1D—H12D | 108.3 | C4G—C6G—H62G | 109.5 |
O1D—C2D—N2D | 123.8 (4) | H61G—C6G—H62G | 109.5 |
O1D—C2D—C1D | 120.6 (4) | C4G—C6G—H63G | 109.5 |
N2D—C2D—C1D | 115.6 (4) | H61G—C6G—H63G | 109.5 |
N2D—C3D—C4D | 109.0 (3) | H62G—C6G—H63G | 109.5 |
N2D—C3D—C7D | 110.0 (3) | O3G—C7G—O2G | 126.2 (4) |
C4D—C3D—C7D | 111.8 (3) | O3G—C7G—C3G | 117.8 (4) |
N2D—C3D—H31D | 108.7 | O2G—C7G—C3G | 115.9 (3) |
C4D—C3D—H31D | 108.7 | ||
C3A—N2A—C2A—O1A | −8.7 (9) | C7D—C3D—C4D—C6D | 54.0 (5) |
C3A—N2A—C2A—C1A | 170.5 (5) | N2D—C3D—C4D—C5D | −60.6 (5) |
N1A—C1A—C2A—O1A | −31.0 (8) | C7D—C3D—C4D—C5D | 177.6 (4) |
N1A—C1A—C2A—N2A | 149.7 (5) | N2D—C3D—C7D—O3D | 146.6 (5) |
C2A—N2A—C3A—C7A | −63.3 (6) | C4D—C3D—C7D—O3D | −92.2 (6) |
C2A—N2A—C3A—C4A | 172.3 (5) | N2D—C3D—C7D—O2D | −35.8 (6) |
N2A—C3A—C4A—C6A | 174.2 (5) | C4D—C3D—C7D—O2D | 85.4 (5) |
C7A—C3A—C4A—C6A | 50.4 (6) | C3E—N2E—C2E—O1E | −10.0 (9) |
N2A—C3A—C4A—C5A | −61.3 (6) | C3E—N2E—C2E—C1E | 171.4 (5) |
C7A—C3A—C4A—C5A | 174.8 (5) | N1E—C1E—C2E—O1E | −16.7 (9) |
N2A—C3A—C7A—O2A | −30.5 (7) | N1E—C1E—C2E—N2E | 161.9 (5) |
C4A—C3A—C7A—O2A | 91.9 (6) | C2E—N2E—C3E—C4E | 170.5 (5) |
N2A—C3A—C7A—O3A | 149.7 (5) | C2E—N2E—C3E—C7E | −64.6 (6) |
C4A—C3A—C7A—O3A | −87.9 (6) | N2E—C3E—C4E—C6E | 173.8 (4) |
C3B—N2B—C2B—O1B | −5.3 (10) | C7E—C3E—C4E—C6E | 50.0 (6) |
C3B—N2B—C2B—C1B | 173.1 (5) | N2E—C3E—C4E—C5E | −61.7 (5) |
N1B—C1B—C2B—O1B | −3.3 (10) | C7E—C3E—C4E—C5E | 174.4 (4) |
N1B—C1B—C2B—N2B | 178.2 (5) | N2E—C3E—C7E—O2E | −27.5 (6) |
C2B—N2B—C3B—C7B | −71.1 (6) | C4E—C3E—C7E—O2E | 95.1 (5) |
C2B—N2B—C3B—C4B | 164.3 (5) | N2E—C3E—C7E—O3E | 152.7 (5) |
N2B—C3B—C4B—C6B | 176.9 (5) | C4E—C3E—C7E—O3E | −84.8 (6) |
C7B—C3B—C4B—C6B | 53.2 (6) | C3F—N2F—C2F—O1F | −9.7 (9) |
N2B—C3B—C4B—C5B | −58.9 (6) | C3F—N2F—C2F—C1F | 171.8 (5) |
C7B—C3B—C4B—C5B | 177.4 (5) | N1F—C1F—C2F—O1F | 8.3 (9) |
N2B—C3B—C7B—O2B | −26.3 (6) | N1F—C1F—C2F—N2F | −173.3 (5) |
C4B—C3B—C7B—O2B | 96.6 (5) | C2F—N2F—C3F—C4F | 168.1 (5) |
N2B—C3B—C7B—O3B | 154.8 (5) | C2F—N2F—C3F—C7F | −68.5 (6) |
C4B—C3B—C7B—O3B | −82.3 (6) | N2F—C3F—C4F—C6F | 178.5 (5) |
C3C—N2C—C2C—O1C | −14.4 (8) | C7F—C3F—C4F—C6F | 56.0 (6) |
C3C—N2C—C2C—C1C | 166.0 (5) | N2F—C3F—C4F—C5F | −57.6 (6) |
N1C—C1C—C2C—O1C | 1.5 (8) | C7F—C3F—C4F—C5F | 179.9 (4) |
N1C—C1C—C2C—N2C | −178.9 (5) | N2F—C3F—C7F—O2F | −29.3 (6) |
C2C—N2C—C3C—C4C | 172.1 (5) | C4F—C3F—C7F—O2F | 92.7 (5) |
C2C—N2C—C3C—C7C | −64.3 (6) | N2F—C3F—C7F—O3F | 151.9 (5) |
N2C—C3C—C4C—C6C | 177.0 (5) | C4F—C3F—C7F—O3F | −86.1 (6) |
C7C—C3C—C4C—C6C | 54.9 (6) | C3G—N2G—C2G—O1G | −13.9 (10) |
N2C—C3C—C4C—C5C | −58.9 (6) | C3G—N2G—C2G—C1G | 164.2 (5) |
C7C—C3C—C4C—C5C | 179.0 (5) | N1G—C1G—C2G—O1G | −17.1 (10) |
N2C—C3C—C7C—O3C | 151.6 (5) | N1G—C1G—C2G—N2G | 164.8 (6) |
C4C—C3C—C7C—O3C | −86.8 (6) | C2G—N2G—C3G—C4G | 178.0 (5) |
N2C—C3C—C7C—O2C | −31.3 (6) | C2G—N2G—C3G—C7G | −60.6 (6) |
C4C—C3C—C7C—O2C | 90.3 (5) | N2G—C3G—C4G—C5G | −60.0 (5) |
C3D—N2D—C2D—O1D | −10.0 (8) | C7G—C3G—C4G—C5G | 179.1 (4) |
C3D—N2D—C2D—C1D | 168.1 (4) | N2G—C3G—C4G—C6G | 175.7 (4) |
N1D—C1D—C2D—O1D | −28.4 (8) | C7G—C3G—C4G—C6G | 54.8 (5) |
N1D—C1D—C2D—N2D | 153.4 (5) | N2G—C3G—C7G—O3G | 147.1 (5) |
C2D—N2D—C3D—C4D | 175.4 (5) | C4G—C3G—C7G—O3G | −92.1 (6) |
C2D—N2D—C3D—C7D | −61.8 (6) | N2G—C3G—C7G—O2G | −35.9 (6) |
N2D—C3D—C4D—C6D | 175.8 (4) | C4G—C3G—C7G—O2G | 85.0 (5) |
Experimental details
Crystal data | |
Chemical formula | C7H14N2O3 |
Mr | 174.20 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 105 |
a, b, c (Å) | 5.5238 (7), 26.581 (3), 44.093 (5) |
V (Å3) | 6474.0 (14) |
Z | 28 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.75 × 0.25 × 0.01 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 35141, 6579, 4122 |
Rint | 0.125 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.073, 0.172, 1.28 |
No. of reflections | 6579 |
No. of parameters | 765 |
No. of restraints | 1101 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.35 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2001), SAINT, SHELXTL (Bruker, 2000), SHELXTL.
Torsion angle | A | B | C | D | E | F | G | Meana | Gly-L-Leu |
N1-C1-C2-N2 (ψ1) | 149.7 (5) | 178.2 (5) | -178.9 (5) | 153.4 (5) | 162.1 (5) | -173.3 (5) | 164.2 (5) | 167.9(14.3) | 171.6 |
C1-C2-N2-C3 (ω1) | 170.5 (5) | 173.1 (5) | 166.0 (5) | 168.1 (4) | 171.4 (5) | 171.8 (5) | 164.2 (5) | 169.3(3.4) | 168.7 |
C2-N2-C3-C7 (ϕ2) | -63.3 (6) | -71.1 (6) | -64.3 (6) | -61.8 (6) | -64.6 (6) | -68.5 (6) | -60.6 (6) | -64.9(3.7) | -64.9 |
N2-C3-C7-O2 (ψT) | -30.5 (7) | -26.3 (6) | -31.3 (6) | -35.8 (6) | -27.5 (6) | -29.3 (6) | -35.9 (6) | -31.0(3.7) | -30.2 |
N2-C3-C4-C5 (χ21,1) | -61.3 (6) | -58.9 (6) | -58.9 (6) | -60.6 (5) | -61.7 (5) | -57.6 (6) | -60.0 (5) | -59.9(1.5) | |
N2-C3-C4-C6 (χ21,1) | 174.2 (5) | 176.9 (5) | 177.0 (5) | 175.8 (4) | 173.8 (4) | 178.5 (5) | 175.7 (4) | 176.0(1.6) | |
H3-N1-C1-C2 | 10.2 | -14.1 | -8.0 | 8.7 | -4.0 | -13.7 | 9.5 | -1.6(10.9) | -1.9 |
RMS | 0.105 | 0.060 | 0.106 | 0.085 | 0.049 | 0.099 | 0.091 | 0.032b |
Notes: (a) Sample standard deviation in parenthesis. (b) Calculated for main-chain atoms and C2β. |
D—H···A | Moleculesa | Mean | Gly-L-Leu | ||||||
N1—H1···O3 | A···Bi | B···Ci | C···Di | D···Ei | E···Fi | F···Gi | G···Aii | ||
H···O | 1.83 | 1.92 | 1.91 | 1.82 | 1.89 | 1.91 | 1.85 | 1.87 | 1.85 |
N···O | 2.727 (6) | 2.788 (6) | 2.797 (6) | 2.719 (6) | 2.768 (7) | 2.802 (6) | 2.751 (7) | 2.765 | 2.750 |
N-H···O | 171 | 159 | 165 | 169 | 162 | 166 | 172 | 166 | 170 |
N1-H2···O2 | A···Giii | B···Fiii | C···Eiii | D···Diii | E···Ciii | F···Biii | G···Aiii | ||
H···O | 1.75 | 1.82 | 1.84 | 1.77 | 1.78 | 1.83 | 1.81 | 1.80 | 1.80 |
N···O | 2.652 (6) | 2.707 (7) | 2.741 (6) | 2.676 (6) | 2.673 (6) | 2.740 (6) | 2.714 (7) | 2.700 | 2.704 |
N-H···O | 171 | 166 | 172 | 173 | 165 | 177 | 173 | 171 | 174 |
N1-H3···O2 | A···B | B···C | C···D | D···E | E···F | F···G | G···Aiv | ||
H···O | 2.02 | 1.98 | 1.99 | 2.03 | 2.00 | 1.97 | 2.03 | 2.00 | 2.05 |
N···O | 2.840 (6) | 2.804 (7) | 2.779 (6) | 2.845 (6) | 2.838 (7) | 2.775 (6) | 2.830 (7) | 2.816 | 2.856 |
N-H···O | 149 | 151 | 145 | 148 | 152 | 147 | 146 | 148 | 147 |
N2-H4···O3 | A···Ai | B···Bi | C···Ci | D···Di | E···Ei | F···Fi | G···Gi | ||
H···O | 2.07 | 2.07 | 2.13 | 2.09 | 2.08 | 2.08 | 2.11 | 2.09 | 2.15 |
N···O | 2.820 (6) | 2.823 (6) | 2.862 (6) | 2.828 (6) | 2.811 (6) | 2.841 (6) | 2.832 (6) | 2.831 | 2.870 |
N-H···O | 143 | 144 | 140 | 141 | 140 | 143 | 139 | 142 | 139 |
Note: (a) Donor molecule···acceptor molecule; for designators see Fig. 1. Symmetry codes: (i) x − 1, y, z; (ii) x − 1, y, z + 1; (iii) x − 1/2, 3/2 − y, 1 − z; (iv) x, y, z + 1. |
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Among dipeptides constructed from the 20 natural amino acids, the Gly–Xaa series of crystal structures, where Xaa is any amino acid, is the most complete for a specific N-terminal amino acid, with 13 entries in the Cambridge Structural Database (CSD, Version 5.27 of November 2005; Allen, 2002). In a student project, we sought to expand this group of structures towards completeness by crystallization of the title compound, Gly-L-Val, (I).
Thin flakes of (I) obtained by slow evaporation were generally of low quality, but a specimen usable for data collection was found after a number of tests. The initial observation of a 44 Å unit-cell axis indicated that this was an unusual dipeptide crystal, a suspicion that was subsequently verified when structure determination revealed seven independent peptide molecules in the asymmetric unit, labelled A to G (Fig. 1). All seven molecules have essentially the same conformation, but with some torsion angle variations, in particular for rotation about the C1—C2 bond (ψ1) (Table 1 and Fig. 2). It is interesting to note that the main chain conformation of Gly-L-Leu [(II); Pattabhi et al., 1974] can be seen to represent an average of the seven Gly-L-Val conformations (Table 1), and the closely related monoclinic structure of (II) provides some clues as to why (I) has crystallized with Z' = 7.
As seen for (II), the crystal structure of (I) is divided into hydrophobic and hydrophilic layers (Fig. 3), and we first suspected that the side-chain modification going from Leu to Val rendered efficient packing of the side chain difficult with Z' limited to 1. To test this hypothesis, a molecular modelling program (SYBYL; Tripos, 2005) was used to construct a theoretical Gly-L-Val structure with Z' = 1, based on (II) but adapted to the correct space group, P212121. This model showed no unfavourable short contacts or large voids compared with the structure of (I).
Our attention then turned to the hydrogen-bonding pattern, with contacts listed in Table 2. Atoms H1 and H3 are involved in head-to-tail chains within a hydrophilic sheet that also comprises the N2—H4···O3 interactions. Two such antiparallel sheets are interconnected by N1—H2···O3 hydrogen bonds and thus generate a hydrophilic layer (Fig. 3). A peculiarity of (II) is the eclipsed conformation of the amino group, as reflected by the H3—N1—C1—C2 torsion angle in Table 1, which is required to minimize the H···O distance in the N1—H3···O2 interaction (Table 2). In (I), two different rotational modes are observed for the amino group, one with H3—N1—C1—C2 < 0° for molecules B, C, E and F, and one with H3—N1—C1—C2 > 0° for molecules A, D and G. The fully eclipsed conformation is thus avoided, and at the same time the associated hydrogen bonds are significantly shorter overall than in (II) (while hydrogen bonds involving atoms H1 and H2 are unchanged).
A further effect of this rearrangement can be seen as a reduction of the structural periodicity along the head-to-tail chains from 6.369 Å for (II) (a axis) to 6.299 Å for (I) (c axis/7). On the other hand, the shorter N2—H4···O3 hydrogen bond in (I) compared with (II) is most probably attributable mainly to more efficient packing of Val than Leu side chains, indicated by a shorter cell axis [5.5238 (7) Å for (I) and 5.565 Å for (II)], as only molecules of the same kind (A···A etc.) are involved.
The monclinic C2 structure of L-Ala-L-Leu hemihydrate (Görbitz, 1999) is related to both (I) and (II) (Fig. 3), with essentially the same molecular conformation. Space for the extra methyl side chain at residue I is nicely provided by insertion of extra water molecules in the hydrophilic layers. Water thus replaces atom O3 as the acceptor in the N1—H2···O3 interaction, and at the same time the two hydrogen-bonded sheets in a single layer (see above) switch from antiparallel to parallel orientation to provide carboxylate acceptors for both water H atoms.
There are only three other structures in the CSD with Z' = 7. Two of these are peptides, viz. L-Met-L-Ala in space group P61 (Görbitz, 2003) and Boc-L-Phe-L-Leu-OBzl, a protected dipeptide fragment of enkephalin, in space group P21 (Antolić et al., 1999). In both cases, the seven molecules exhibit a mixture of conformations, particularly with regard to the side chains, but also with extensive flexibility for the peptide main chains. The third compound, 2-cyano-2-isonitroso-N-morpholinylacetamide [(III); Eddings et al., 2004], shares the P212121 space group with (I) and, with its 7.3 × 14.4 × 54.8 Å unit cell, shows some of the same packing features, but not the division into hydrophobic and hydrophilic layers as seen for (I). In (III), there is a 4:3 distribution between two different chair conformations for the six-membered ring.