Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270110020895/jz3182sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270110020895/jz3182Isup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108270110020895/jz3182sup3.pdf |
CCDC reference: 786813
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); 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).
C10H19N3O4·1.094H2O | Dx = 1.287 Mg m−3 |
Mr = 265.01 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 50.56 reflections |
a = 4.7855 (4) Å | θ = 1.3–28.3° |
b = 18.2887 (15) Å | µ = 0.10 mm−1 |
c = 31.247 (3) Å | T = 105 K |
V = 2734.8 (4) Å3 | Block, colourless |
Z = 8 | 0.78 × 0.50 × 0.22 mm |
F(000) = 1144 |
Bruker APEXII CCD area-detector diffractometer | 3860 independent reflections |
Radiation source: fine-focus sealed tube | 2902 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.060 |
Detector resolution: 8.3 pixels mm-1 | θmax = 28.3°, θmin = 1.3° |
Three sets of frames each taken over 0.3° ω rotation with 20 s exposure time. Detector set at 2θ = 26°, crystal–to–detector distance 6.00 cm. scans | h = −5→6 |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | k = −24→21 |
Tmin = 0.751, Tmax = 0.978 | l = −40→41 |
18243 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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0479P)2 + 0.6738P] where P = (Fo2 + 2Fc2)/3 |
3860 reflections | (Δ/σ)max = 0.001 |
376 parameters | Δρmax = 0.22 e Å−3 |
25 restraints | Δρmin = −0.23 e Å−3 |
Experimental. Crystallized from water and 2-propanol |
Refinement. Refinement of F2 against ALL reflections. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1A | 1.2190 (3) | 0.45870 (9) | 0.26437 (5) | 0.0268 (4) | |
O2A | 1.1326 (4) | 0.29647 (9) | 0.20361 (7) | 0.0501 (6) | |
N1A | 0.9555 (4) | 0.41979 (9) | 0.34181 (5) | 0.0212 (4) | |
H1A | 0.9141 | 0.3737 | 0.3329 | 0.032* | |
H2A | 0.8832 | 0.4271 | 0.3684 | 0.032* | |
H3A | 1.1443 | 0.4256 | 0.3427 | 0.032* | |
N2A | 0.7851 (3) | 0.44876 (8) | 0.23547 (5) | 0.0155 (4) | |
H4A | 0.6050 | 0.4485 | 0.2411 | 0.019* | |
N3A | 0.7000 (4) | 0.25330 (9) | 0.21399 (6) | 0.0287 (5) | |
H5A | 0.7613 | 0.2152 | 0.2284 | 0.034* | |
H6A | 0.5196 | 0.2591 | 0.2097 | 0.034* | |
C1A | 0.8328 (4) | 0.47381 (10) | 0.31154 (6) | 0.0164 (4) | |
H11A | 0.6263 | 0.4659 | 0.3098 | 0.020* | |
C2A | 0.8904 (5) | 0.55316 (11) | 0.32538 (6) | 0.0208 (5) | |
H21A | 1.0968 | 0.5616 | 0.3242 | 0.025* | |
C3A | 0.7907 (7) | 0.56896 (12) | 0.37101 (7) | 0.0376 (7) | |
H31A | 0.5854 | 0.5626 | 0.3722 | 0.045* | |
H32A | 0.8756 | 0.5328 | 0.3907 | 0.045* | |
C4A | 0.8639 (8) | 0.64568 (14) | 0.38650 (8) | 0.0525 (9) | |
H41A | 0.8245 | 0.6496 | 0.4172 | 0.079* | |
H42A | 0.7515 | 0.6816 | 0.3709 | 0.079* | |
H43A | 1.0627 | 0.6551 | 0.3814 | 0.079* | |
C5A | 0.7509 (6) | 0.60483 (11) | 0.29337 (7) | 0.0324 (6) | |
H51A | 0.7966 | 0.6555 | 0.3008 | 0.049* | |
H52A | 0.5479 | 0.5980 | 0.2944 | 0.049* | |
H53A | 0.8189 | 0.5940 | 0.2645 | 0.049* | |
C6A | 0.9630 (4) | 0.45919 (10) | 0.26765 (6) | 0.0163 (4) | |
C8A | 0.7595 (5) | 0.36546 (10) | 0.17401 (6) | 0.0204 (5) | |
H81A | 0.5533 | 0.3651 | 0.1764 | 0.024* | |
H82A | 0.8092 | 0.3607 | 0.1434 | 0.024* | |
C9A | 0.8793 (5) | 0.30183 (11) | 0.19866 (7) | 0.0247 (5) | |
C7A | 0.8735 (4) | 0.43776 (10) | 0.19150 (6) | 0.0159 (4) | 0.812 (2) |
H71A | 1.0819 | 0.4337 | 0.1917 | 0.019* | 0.812 (2) |
C10A | 0.7989 (5) | 0.50320 (10) | 0.16254 (6) | 0.0181 (5) | 0.812 (2) |
O3A | 0.7196 (4) | 0.56185 (7) | 0.18000 (5) | 0.0226 (4) | 0.812 (2) |
O4A | 0.8293 (4) | 0.49360 (9) | 0.12294 (4) | 0.0199 (4) | 0.812 (2) |
C71A | 0.8735 (4) | 0.43776 (10) | 0.19150 (6) | 0.0159 (4) | 0.188 (2) |
H72A | 1.0822 | 0.4353 | 0.1910 | 0.019* | 0.188 (2) |
C11A | 0.7808 (11) | 0.4991 (2) | 0.16068 (10) | 0.0181 (5) | 0.188 (2) |
O31A | 0.6080 (9) | 0.5460 (2) | 0.17402 (14) | 0.030* | 0.188 (2) |
O41A | 0.8709 (14) | 0.4947 (3) | 0.12293 (9) | 0.0199 (4) | 0.188 (2) |
O1B | 0.5777 (3) | 0.39876 (7) | 0.52851 (4) | 0.0202 (3) | |
O2B | 0.5780 (3) | 0.19722 (7) | 0.41309 (5) | 0.0215 (3) | |
O3B | 0.7463 (3) | 0.41106 (7) | 0.42507 (4) | 0.0208 (3) | |
O4B | 0.4277 (3) | 0.37045 (8) | 0.37892 (4) | 0.0259 (4) | |
N1B | 0.1538 (4) | 0.45197 (8) | 0.58124 (5) | 0.0178 (4) | |
H1B | 0.1400 | 0.4026 | 0.5843 | 0.027* | |
H2B | 0.0033 | 0.4738 | 0.5936 | 0.027* | |
H3B | 0.3130 | 0.4680 | 0.5941 | 0.027* | |
N2B | 0.2361 (3) | 0.38184 (8) | 0.47855 (5) | 0.0152 (4) | |
H4B | 0.0634 | 0.3927 | 0.4713 | 0.018* | |
N3B | 0.1701 (4) | 0.18564 (9) | 0.37793 (5) | 0.0233 (4) | |
H5B | 0.2387 | 0.1518 | 0.3609 | 0.028* | |
H6B | −0.0047 | 0.1998 | 0.3751 | 0.028* | |
C1B | 0.1623 (4) | 0.47080 (10) | 0.53461 (6) | 0.0165 (4) | |
H11B | −0.0306 | 0.4684 | 0.5224 | 0.020* | |
C2B | 0.2835 (5) | 0.54817 (10) | 0.52808 (6) | 0.0209 (5) | |
H21B | 0.4688 | 0.5503 | 0.5428 | 0.025* | |
C3B | 0.0949 (6) | 0.60635 (11) | 0.54807 (8) | 0.0361 (7) | |
H31B | −0.0792 | 0.6097 | 0.5311 | 0.043* | |
H32B | 0.0431 | 0.5905 | 0.5773 | 0.043* | |
C4B | 0.2264 (7) | 0.68202 (13) | 0.55069 (10) | 0.0517 (8) | |
H41B | 0.3975 | 0.6796 | 0.5678 | 0.078* | |
H42B | 0.0945 | 0.7160 | 0.5641 | 0.078* | |
H43B | 0.2717 | 0.6992 | 0.5218 | 0.078* | |
C5B | 0.3320 (6) | 0.56207 (12) | 0.48041 (7) | 0.0345 (6) | |
H51B | 0.4683 | 0.5268 | 0.4694 | 0.052* | |
H52B | 0.4036 | 0.6118 | 0.4764 | 0.052* | |
H53B | 0.1553 | 0.5566 | 0.4649 | 0.052* | |
C6B | 0.3452 (4) | 0.41319 (10) | 0.51357 (6) | 0.0159 (4) | |
C7B | 0.3928 (4) | 0.33022 (10) | 0.45191 (6) | 0.0140 (4) | |
H71B | 0.5409 | 0.3065 | 0.4697 | 0.017* | |
C8B | 0.1922 (4) | 0.27172 (10) | 0.43579 (6) | 0.0176 (5) | |
H81B | 0.1065 | 0.2469 | 0.4607 | 0.021* | |
H82B | 0.0404 | 0.2956 | 0.4194 | 0.021* | |
C9B | 0.3301 (4) | 0.21541 (10) | 0.40785 (6) | 0.0161 (4) | |
C10B | 0.5334 (4) | 0.37404 (10) | 0.41555 (6) | 0.0158 (4) | |
O1W | 0.7319 (5) | 0.28591 (11) | 0.32034 (7) | 0.0442 (6) | 0.812 (2) |
H11W | 0.718 (6) | 0.2417 (5) | 0.3121 (8) | 0.066* | 0.812 (2) |
H12W | 0.587 (3) | 0.2942 (11) | 0.3360 (6) | 0.066* | 0.812 (2) |
O2W | 0.7654 (4) | 0.14272 (9) | 0.29047 (6) | 0.0448 (5) | |
H22W | 0.630 (2) | 0.1143 (7) | 0.2960 (9) | 0.067* | |
H21W | 0.912 (2) | 0.1204 (12) | 0.2988 (10) | 0.067* | 0.812 (2) |
H23W | 0.699 (6) | 0.1857 (6) | 0.293 (3) | 0.067* | 0.188 (2) |
O3W | 1.1345 (19) | 0.2854 (4) | 0.2968 (2) | 0.042 (2)* | 0.188 (2) |
H31W | 1.164 (9) | 0.293 (2) | 0.2702 (3) | 0.064* | 0.188 (2) |
H32W | 1.044 (5) | 0.2453 (9) | 0.2971 (14) | 0.064* | 0.188 (2) |
O4W | 0.4496 (18) | 0.2933 (7) | 0.2991 (3) | 0.077 (4)* | 0.188 (2) |
H41W | 0.412 (6) | 0.301 (2) | 0.3253 (5) | 0.116* | 0.188 (2) |
H42W | 0.629 (2) | 0.291 (9) | 0.2981 (15) | 0.116* | 0.188 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0074 (7) | 0.0504 (9) | 0.0227 (7) | 0.0015 (7) | 0.0009 (6) | 0.0002 (7) |
O2A | 0.0154 (8) | 0.0245 (8) | 0.1103 (17) | 0.0016 (7) | −0.0026 (10) | 0.0180 (9) |
N1A | 0.0164 (9) | 0.0282 (9) | 0.0191 (8) | 0.0036 (8) | −0.0007 (7) | 0.0041 (7) |
N2A | 0.0080 (8) | 0.0207 (8) | 0.0177 (7) | 0.0003 (7) | 0.0023 (7) | 0.0041 (6) |
N3A | 0.0156 (9) | 0.0228 (8) | 0.0478 (11) | 0.0000 (8) | −0.0028 (9) | 0.0124 (8) |
C1A | 0.0084 (9) | 0.0236 (9) | 0.0173 (9) | 0.0015 (8) | −0.0002 (8) | 0.0065 (8) |
C2A | 0.0134 (10) | 0.0268 (10) | 0.0220 (10) | −0.0025 (9) | −0.0005 (8) | 0.0028 (8) |
C3A | 0.0555 (17) | 0.0290 (11) | 0.0282 (12) | 0.0031 (12) | 0.0063 (12) | −0.0007 (9) |
C4A | 0.090 (2) | 0.0353 (13) | 0.0327 (13) | 0.0065 (16) | 0.0038 (16) | −0.0068 (11) |
C5A | 0.0430 (15) | 0.0226 (10) | 0.0317 (12) | −0.0005 (11) | −0.0041 (11) | 0.0064 (9) |
C6A | 0.0132 (10) | 0.0171 (9) | 0.0186 (9) | 0.0018 (8) | 0.0014 (8) | 0.0046 (8) |
C8A | 0.0176 (10) | 0.0190 (9) | 0.0245 (10) | −0.0006 (9) | −0.0003 (9) | 0.0017 (8) |
C9A | 0.0190 (11) | 0.0170 (9) | 0.0382 (12) | 0.0000 (9) | −0.0023 (10) | 0.0010 (9) |
C7A | 0.0110 (9) | 0.0184 (9) | 0.0182 (9) | 0.0014 (8) | 0.0013 (8) | 0.0020 (8) |
C10A | 0.0146 (10) | 0.0180 (9) | 0.0218 (10) | −0.0030 (9) | 0.0037 (9) | 0.0039 (8) |
O3A | 0.0298 (11) | 0.0141 (7) | 0.0238 (9) | 0.0011 (8) | 0.0044 (8) | 0.0024 (7) |
O4A | 0.0174 (8) | 0.0254 (7) | 0.0170 (7) | −0.0024 (7) | −0.0003 (6) | 0.0032 (6) |
C71A | 0.0110 (9) | 0.0184 (9) | 0.0182 (9) | 0.0014 (8) | 0.0013 (8) | 0.0020 (8) |
C11A | 0.0146 (10) | 0.0180 (9) | 0.0218 (10) | −0.0030 (9) | 0.0037 (9) | 0.0039 (8) |
O41A | 0.0174 (8) | 0.0254 (7) | 0.0170 (7) | −0.0024 (7) | −0.0003 (6) | 0.0032 (6) |
O1B | 0.0134 (7) | 0.0254 (7) | 0.0217 (7) | −0.0001 (6) | −0.0025 (6) | −0.0037 (6) |
O2B | 0.0136 (7) | 0.0211 (7) | 0.0298 (8) | 0.0019 (6) | −0.0023 (6) | −0.0030 (6) |
O3B | 0.0181 (7) | 0.0216 (6) | 0.0228 (7) | −0.0042 (7) | −0.0001 (6) | 0.0020 (6) |
O4B | 0.0192 (7) | 0.0411 (8) | 0.0173 (7) | −0.0005 (7) | −0.0018 (6) | 0.0045 (6) |
N1B | 0.0143 (8) | 0.0177 (7) | 0.0212 (8) | −0.0019 (7) | 0.0043 (7) | −0.0021 (7) |
N2B | 0.0088 (8) | 0.0202 (7) | 0.0167 (8) | 0.0024 (7) | −0.0021 (7) | −0.0037 (6) |
N3B | 0.0167 (9) | 0.0275 (9) | 0.0257 (9) | 0.0071 (8) | −0.0027 (8) | −0.0091 (7) |
C1B | 0.0110 (9) | 0.0230 (9) | 0.0155 (9) | −0.0001 (8) | −0.0013 (8) | −0.0029 (7) |
C2B | 0.0192 (10) | 0.0194 (9) | 0.0240 (10) | −0.0043 (9) | 0.0004 (9) | −0.0026 (8) |
C3B | 0.0388 (15) | 0.0213 (11) | 0.0481 (15) | −0.0021 (11) | 0.0132 (13) | −0.0054 (10) |
C4B | 0.063 (2) | 0.0249 (12) | 0.0675 (19) | −0.0033 (14) | 0.0103 (17) | −0.0119 (12) |
C5B | 0.0488 (16) | 0.0272 (11) | 0.0275 (11) | −0.0009 (12) | 0.0049 (12) | 0.0057 (9) |
C6B | 0.0136 (10) | 0.0154 (9) | 0.0187 (9) | −0.0035 (8) | 0.0036 (8) | 0.0004 (8) |
C7B | 0.0096 (9) | 0.0171 (9) | 0.0154 (9) | −0.0003 (8) | 0.0019 (8) | −0.0015 (7) |
C8B | 0.0150 (10) | 0.0173 (9) | 0.0206 (10) | −0.0008 (8) | 0.0018 (9) | −0.0032 (7) |
C9B | 0.0142 (10) | 0.0156 (9) | 0.0184 (9) | −0.0016 (8) | 0.0023 (8) | −0.0007 (7) |
C10B | 0.0130 (10) | 0.0150 (8) | 0.0193 (10) | 0.0052 (8) | 0.0006 (8) | −0.0009 (8) |
O1W | 0.0431 (13) | 0.0392 (11) | 0.0503 (13) | −0.0054 (12) | 0.0148 (12) | −0.0166 (10) |
O2W | 0.0348 (10) | 0.0475 (10) | 0.0522 (11) | −0.0107 (9) | −0.0046 (9) | 0.0118 (9) |
O1A—C6A | 1.230 (3) | N1B—C1B | 1.498 (2) |
O2A—C9A | 1.226 (3) | N1B—H1B | 0.9100 |
N1A—C1A | 1.489 (2) | N1B—H2B | 0.9100 |
N1A—H1A | 0.9100 | N1B—H3B | 0.9100 |
N1A—H2A | 0.9100 | N2B—C6B | 1.341 (2) |
N1A—H3A | 0.9100 | N2B—C7B | 1.465 (2) |
N2A—C6A | 1.331 (3) | N2B—H4B | 0.8800 |
N2A—C7A | 1.452 (2) | N3B—C9B | 1.325 (3) |
N2A—H4A | 0.8800 | N3B—H5B | 0.8800 |
N3A—C9A | 1.324 (3) | N3B—H6B | 0.8800 |
N3A—H5A | 0.8800 | C1B—C6B | 1.519 (3) |
N3A—H6A | 0.8800 | C1B—C2B | 1.543 (3) |
C1A—C6A | 1.530 (3) | C1B—H11B | 1.0000 |
C1A—C2A | 1.539 (3) | C2B—C3B | 1.529 (3) |
C1A—H11A | 1.0000 | C2B—C5B | 1.529 (3) |
C2A—C5A | 1.529 (3) | C2B—H21B | 1.0000 |
C2A—C3A | 1.531 (3) | C3B—C4B | 1.522 (3) |
C2A—H21A | 1.0000 | C3B—H31B | 0.9900 |
C3A—C4A | 1.525 (3) | C3B—H32B | 0.9900 |
C3A—H31A | 0.9900 | C4B—H41B | 0.9800 |
C3A—H32A | 0.9900 | C4B—H42B | 0.9800 |
C4A—H41A | 0.9800 | C4B—H43B | 0.9800 |
C4A—H42A | 0.9800 | C5B—H51B | 0.9800 |
C4A—H43A | 0.9800 | C5B—H52B | 0.9800 |
C5A—H51A | 0.9800 | C5B—H53B | 0.9800 |
C5A—H52A | 0.9800 | C7B—C8B | 1.523 (3) |
C5A—H53A | 0.9800 | C7B—C10B | 1.545 (3) |
C8A—C9A | 1.509 (3) | C7B—H71B | 1.0000 |
C8A—C7A | 1.531 (3) | C8B—C9B | 1.503 (3) |
C8A—H81A | 0.9900 | C8B—H81B | 0.9900 |
C8A—H82A | 0.9900 | C8B—H82B | 0.9900 |
C7A—C10A | 1.542 (3) | O1W—H11W | 0.852 (9) |
C7A—H71A | 1.0000 | O1W—H12W | 0.860 (9) |
C10A—O4A | 1.258 (2) | O2W—H21W | 0.853 (9) |
C10A—O3A | 1.262 (2) | O2W—H22W | 0.850 (8) |
C11A—O41A | 1.259 (3) | O2W—H23W | 0.852 (10) |
C11A—O31A | 1.262 (3) | O3W—H31W | 0.855 (9) |
O1B—C6B | 1.235 (2) | O3W—H32W | 0.854 (9) |
O2B—C9B | 1.243 (3) | O4W—H41W | 0.850 (10) |
O3B—C10B | 1.259 (2) | O4W—H42W | 0.858 (9) |
O4B—C10B | 1.253 (2) | ||
C1A—N1A—H1A | 109.5 | H1B—N1B—H2B | 109.5 |
C1A—N1A—H2A | 109.5 | C1B—N1B—H3B | 109.5 |
H1A—N1A—H2A | 109.5 | H1B—N1B—H3B | 109.5 |
C1A—N1A—H3A | 109.5 | H2B—N1B—H3B | 109.5 |
H1A—N1A—H3A | 109.5 | C6B—N2B—C7B | 122.67 (17) |
H2A—N1A—H3A | 109.5 | C6B—N2B—H4B | 118.7 |
C6A—N2A—C7A | 123.27 (17) | C7B—N2B—H4B | 118.7 |
C6A—N2A—H4A | 118.4 | C9B—N3B—H5B | 120.0 |
C7A—N2A—H4A | 118.4 | C9B—N3B—H6B | 120.0 |
C9A—N3A—H5A | 120.0 | H5B—N3B—H6B | 120.0 |
C9A—N3A—H6A | 120.0 | N1B—C1B—C6B | 106.09 (15) |
H5A—N3A—H6A | 120.0 | N1B—C1B—C2B | 110.47 (15) |
N1A—C1A—C6A | 107.05 (15) | C6B—C1B—C2B | 111.23 (16) |
N1A—C1A—C2A | 112.11 (15) | N1B—C1B—H11B | 109.7 |
C6A—C1A—C2A | 110.10 (16) | C6B—C1B—H11B | 109.7 |
N1A—C1A—H11A | 109.2 | C2B—C1B—H11B | 109.7 |
C6A—C1A—H11A | 109.2 | C3B—C2B—C5B | 111.85 (18) |
C2A—C1A—H11A | 109.2 | C3B—C2B—C1B | 111.24 (18) |
C5A—C2A—C3A | 110.87 (19) | C5B—C2B—C1B | 109.79 (16) |
C5A—C2A—C1A | 108.70 (16) | C3B—C2B—H21B | 107.9 |
C3A—C2A—C1A | 112.57 (17) | C5B—C2B—H21B | 107.9 |
C5A—C2A—H21A | 108.2 | C1B—C2B—H21B | 107.9 |
C3A—C2A—H21A | 108.2 | C4B—C3B—C2B | 114.3 (2) |
C1A—C2A—H21A | 108.2 | C4B—C3B—H31B | 108.7 |
C4A—C3A—C2A | 113.4 (2) | C2B—C3B—H31B | 108.7 |
C4A—C3A—H31A | 108.9 | C4B—C3B—H32B | 108.7 |
C2A—C3A—H31A | 108.9 | C2B—C3B—H32B | 108.7 |
C4A—C3A—H32A | 108.9 | H31B—C3B—H32B | 107.6 |
C2A—C3A—H32A | 108.9 | C3B—C4B—H41B | 109.5 |
H31A—C3A—H32A | 107.7 | C3B—C4B—H42B | 109.5 |
C3A—C4A—H41A | 109.5 | H41B—C4B—H42B | 109.5 |
C3A—C4A—H42A | 109.5 | C3B—C4B—H43B | 109.5 |
H41A—C4A—H42A | 109.5 | H41B—C4B—H43B | 109.5 |
C3A—C4A—H43A | 109.5 | H42B—C4B—H43B | 109.5 |
H41A—C4A—H43A | 109.5 | C2B—C5B—H51B | 109.5 |
H42A—C4A—H43A | 109.5 | C2B—C5B—H52B | 109.5 |
C2A—C5A—H51A | 109.5 | H51B—C5B—H52B | 109.5 |
C2A—C5A—H52A | 109.5 | C2B—C5B—H53B | 109.5 |
H51A—C5A—H52A | 109.5 | H51B—C5B—H53B | 109.5 |
C2A—C5A—H53A | 109.5 | H52B—C5B—H53B | 109.5 |
H51A—C5A—H53A | 109.5 | O1B—C6B—N2B | 124.60 (18) |
H52A—C5A—H53A | 109.5 | O1B—C6B—C1B | 120.22 (17) |
O1A—C6A—N2A | 124.98 (18) | N2B—C6B—C1B | 115.17 (17) |
O1A—C6A—C1A | 118.79 (18) | N2B—C7B—C8B | 108.53 (16) |
N2A—C6A—C1A | 116.22 (17) | N2B—C7B—C10B | 107.86 (14) |
C9A—C8A—C7A | 110.40 (16) | C8B—C7B—C10B | 113.31 (16) |
C9A—C8A—H81A | 109.6 | N2B—C7B—H71B | 109.0 |
C7A—C8A—H81A | 109.6 | C8B—C7B—H71B | 109.0 |
C9A—C8A—H82A | 109.6 | C10B—C7B—H71B | 109.0 |
C7A—C8A—H82A | 109.6 | C9B—C8B—C7B | 113.37 (17) |
H81A—C8A—H82A | 108.1 | C9B—C8B—H81B | 108.9 |
O2A—C9A—N3A | 122.8 (2) | C7B—C8B—H81B | 108.9 |
O2A—C9A—C8A | 120.1 (2) | C9B—C8B—H82B | 108.9 |
N3A—C9A—C8A | 117.11 (19) | C7B—C8B—H82B | 108.9 |
N2A—C7A—C8A | 110.72 (15) | H81B—C8B—H82B | 107.7 |
N2A—C7A—C10A | 112.36 (15) | O2B—C9B—N3B | 122.31 (18) |
C8A—C7A—C10A | 112.22 (16) | O2B—C9B—C8B | 121.73 (18) |
N2A—C7A—H71A | 107.1 | N3B—C9B—C8B | 115.95 (18) |
C8A—C7A—H71A | 107.1 | O4B—C10B—O3B | 124.80 (18) |
C10A—C7A—H71A | 107.1 | O4B—C10B—C7B | 117.97 (18) |
O4A—C10A—O3A | 125.37 (17) | O3B—C10B—C7B | 117.23 (17) |
O4A—C10A—C7A | 116.22 (16) | H11W—O1W—H12W | 105.9 (19) |
O3A—C10A—C7A | 118.39 (16) | H22W—O2W—H21W | 105.9 (15) |
O41A—C11A—O31A | 125.2 (3) | H22W—O2W—H23W | 105.0 (19) |
C1B—N1B—H1B | 109.5 | H31W—O3W—H32W | 104 (2) |
C1B—N1B—H2B | 109.5 | H41W—O4W—H42W | 105 (2) |
N1A—C1A—C6A—N2A | 126.30 (18) | C5A—C2A—C3A—C4A | −62.0 (3) |
C1A—C6A—N2A—C7A | 176.95 (15) | C7A—N2A—C6A—O1A | −2.2 (3) |
C6A—N2A—C7A—C10A | −110.5 (2) | N1A—C1A—C6A—O1A | −54.5 (2) |
N2A—C7A—C10A—O3A | 12.1 (3) | C2A—C1A—C6A—O1A | 67.6 (2) |
C6A—N2A—C7A—C11A | −115.5 (3) | C2A—C1A—C6A—N2A | −111.60 (19) |
N2A—C7A—C11A—O31A | −10.2 (6) | C6A—N2A—C7A—C8A | 123.10 (19) |
N1A—C1A—C2A—C3A | −55.2 (2) | C6A—N2A—C7A—C10A | −110.5 (2) |
N1A—C1A—C2A—C5A | −178.44 (17) | C9A—C8A—C7A—C10A | 169.92 (18) |
C1A—C2A—C3A—C4A | 176.0 (2) | N2A—C7A—C10A—O4A | −169.5 (2) |
N2A—C7A—C8A—C9A | −63.7 (2) | C8A—C7A—C10A—O4A | −44.0 (3) |
C7A—C8A—C9A—O2A | −51.6 (3) | C8A—C7A—C10A—O3A | 137.6 (2) |
C7A—C8A—C9A—N3A | 128.7 (2) | C6B—C1B—C2B—C3B | 178.27 (18) |
N1B—C1B—C6B—N2B | 130.70 (17) | C6B—C1B—C2B—C5B | 53.9 (2) |
C1B—C6B—N2B—C7B | 174.21 (15) | C5B—C2B—C3B—C4B | −68.2 (3) |
C6B—N2B—C7B—C10B | −93.1 (2) | C7B—N2B—C6B—O1B | −4.9 (3) |
N2B—C7B—C10B—O3B | 75.8 (2) | N1B—C1B—C6B—O1B | −50.1 (2) |
N1B—C1B—C2B—C3B | −64.2 (2) | C2B—C1B—C6B—O1B | 70.0 (2) |
N1B—C1B—C2B—C5B | 171.47 (19) | C2B—C1B—C6B—N2B | −109.13 (19) |
C1B—C2B—C3B—C4B | 168.6 (2) | C6B—N2B—C7B—C8B | 143.78 (17) |
N2B—C7B—C8B—C9B | 179.88 (15) | C10B—C7B—C8B—C9B | 60.1 (2) |
C7B—C8B—C9B—O2B | 31.5 (3) | N2B—C7B—C10B—O4B | −103.91 (19) |
C7B—C8B—C9B—N3B | −149.65 (17) | C8B—C7B—C10B—O4B | 16.2 (2) |
C6A—C1A—C2A—C5A | 62.5 (2) | C8B—C7B—C10B—O3B | −164.00 (16) |
C6A—C1A—C2A—C3A | −174.27 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O1W | 0.91 | 1.87 | 2.755 (3) | 164 |
N1A—H1A···O3W | 0.91 | 2.23 | 2.959 (8) | 136 |
N1A—H2A···O3B | 0.91 | 1.91 | 2.792 (2) | 163 |
N1A—H3A···O4Bi | 0.91 | 2.03 | 2.695 (2) | 128 |
N2A—H4A···O1Aii | 0.88 | 1.99 | 2.862 (2) | 169 |
N3A—H5A···O2W | 0.88 | 2.35 | 3.146 (2) | 151 |
N3A—H6A···O2Aii | 0.88 | 1.98 | 2.846 (3) | 167 |
C1A—H11A···O1Aii | 1.00 | 2.41 | 3.298 (2) | 147 |
C8A—H81A···O2Aii | 0.99 | 2.52 | 3.383 (3) | 146 |
N1B—H1B···O2Biii | 0.91 | 1.85 | 2.758 (2) | 174 |
N1B—H2B···O4Aiv | 0.91 | 1.93 | 2.835 (2) | 172 |
N1B—H3B···O4Av | 0.91 | 2.06 | 2.968 (2) | 179 |
N2B—H4B···O3Bii | 0.88 | 2.12 | 2.928 (2) | 152 |
N3B—H5B···O3Avi | 0.88 | 2.09 | 2.946 (2) | 163 |
N3B—H6B···O2Bii | 0.88 | 2.32 | 3.046 (2) | 139 |
C1B—H11B···O1Bii | 1.00 | 2.27 | 3.098 (2) | 139 |
C8B—H82B···O3Bii | 0.99 | 2.54 | 3.341 (2) | 137 |
O1W—H11W···O2W | 0.85 (1) | 1.95 (1) | 2.785 (3) | 168 (3) |
O1W—H12W···O4B | 0.86 (1) | 2.08 (1) | 2.804 (3) | 141 (2) |
O2W—H21W···O3Avii | 0.85 (1) | 2.17 (1) | 3.019 (3) | 179 (2) |
O2W—H22W···O3Avi | 0.85 (1) | 2.07 (1) | 2.903 (3) | 167 (2) |
O2W—H22W···O31Avi | 0.85 (1) | 1.93 (1) | 2.749 (4) | 161 (2) |
O2W—H23W···O4W | 0.85 (1) | 2.31 (2) | 3.153 (12) | 170 (4) |
O3W—H31W···O2A | 0.86 (1) | 2.09 (1) | 2.917 (8) | 164 (4) |
O3W—H32W···O2W | 0.85 (1) | 2.31 (1) | 3.157 (8) | 172 (4) |
O4W—H41W···O4B | 0.85 (1) | 2.10 (2) | 2.867 (10) | 150 (4) |
O4W—H42W···O3W | 0.86 (1) | 2.42 (1) | 3.281 (12) | 179 (6) |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) x−1/2, −y+1/2, −z+1; (iv) −x+1/2, −y+1, z+1/2; (v) −x+3/2, −y+1, z+1/2; (vi) −x+1, y−1/2, −z+1/2; (vii) −x+2, y−1/2, −z+1/2. |
Molecule A | Molecule B | |
N1—C1—C6—N2 | 126.30 (18) | 130.70 (17) |
C1—C6—N2—C7 | 176.95 (15) | 174.21 (15) |
C6—N2—C7—C10 | -110.5 (2) | -93.1 (2) |
N2—C7—C10—O3 | 12.1 (3) | 75.8 (2) |
C6—N2—C7—C11 | -115.5 (3) | |
N2—C7—C11—O31 | -10.2 (6) | |
N1—C1—C2—C3 | -55.2 (2) | -64.2 (2) |
N1—C1—C2—C5 | -178.44 (17) | 171.47 (19) |
C1—C2—C3—C4 | 176.0 (2) | 168.6 (2) |
N2—C7—C8—C9 | -63.7 (2) | 179.88 (15) |
C7—C8—C9—O2 | -51.6 (3) | 31.5 (3) |
C7—C8—C9—N3 | 128.7 (2) | -149.65 (17) |
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