Experimental electron densities and derived properties have been determined for the two energetic materials CL-20 (3,5,9,11-tetraacetyl-14-oxo-1,3,5,7,9,11-hexaazapentacyclo-[5.5.3.02,6.04,10.08,12]pentadecane), and FOX-7 (1,1-diamino-2,2-dinitroethylene) from single-crystal diffraction. Synchrotron data extending to high scattering angles were measured at low temperature. Low figures-of-merit and excellent residuals were obtained. The Hansen & Coppens multipole-model electron density was compared with results from theoretical calculations via structure factors simulating an experiment. Chemical bonding in the molecules is discussed and a topological analysis gives insight especially into the character of those bonds that are thought to play a key role in the decomposition of the molecules. A comparison of theoretical and experimental electrostatic potentials shows no obvious evidence supporting earlier findings on other nitroheterocyclic molecules that electron-density maxima near the C-NO2 bonds mapped on the electron-density isosurface can be correlated with impact sensitivities. For FOX-7 periodic Hartree-Fock calculations were performed to investigate the influence of the crystal field on the electron density distribution.
Supporting information
CCDC references: 679945; 679946
For both compounds, program(s) used to refine structure: Koritsanszky et al., (2003); molecular graphics: Koritsanszky et al., (2003); software used to prepare material for publication: Koritsanszky et al., (2003).
Crystal data top
C2H4N4O4 | Z = 4 |
Mr = 148.09 | Dx = 1.941 (1) Mg m−3 |
Monoclinic, P21/n | Synchrotron radiation, λ = ? Å |
a = 6.922 (1) Å | µ = 0.78 mm−1 |
b = 6.501 (1) Å | T = 100 K |
c = 11.262 (1) Å | Prismatic, yellow |
β = 90.485 (1)° | 0.27 × 0.25 × 0.22 mm |
V = 506.77 Å3 | |
Data collection top
Beamline E2; HASYLAB-DESY diffractometer | Rint = 2.7 |
rotation photographs scans | θmax = 33.6° |
143788 measured reflections | h = ?→? |
6093 independent reflections | k = ?→? |
5329 reflections with I > 3σ(I) | l = ?→? |
Refinement top
Refinement on F | 0 restraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.021 | w1 = 1/[s2(Fo)] |
wR(F2) = 0.027 | (Δ/σ)max < 0.001 |
S = 2.05 | Δρmax = 0.29 e Å−3 |
5329 reflections | Δρmin = −0.36 e Å−3 |
184 parameters | |
Crystal data top
C2H4N4O4 | V = 506.77 Å3 |
Mr = 148.09 | Z = 4 |
Monoclinic, P21/n | Synchrotron radiation, λ = ? Å |
a = 6.922 (1) Å | µ = 0.78 mm−1 |
b = 6.501 (1) Å | T = 100 K |
c = 11.262 (1) Å | 0.27 × 0.25 × 0.22 mm |
β = 90.485 (1)° | |
Data collection top
Beamline E2; HASYLAB-DESY diffractometer | 5329 reflections with I > 3σ(I) |
143788 measured reflections | Rint = 2.7 |
6093 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.021 | 0 restraints |
wR(F2) = 0.027 | All H-atom parameters refined |
S = 2.05 | Δρmax = 0.29 e Å−3 |
5329 reflections | Δρmin = −0.36 e Å−3 |
184 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O(11) | 0.19465 (3) | 0.33585 (3) | 0.337060 (10) | 0.012 | |
O(12) | −0.02049 (2) | 0.44648 (3) | 0.212860 (10) | 0.012 | |
O(21) | 0.58078 (2) | 0.30104 (3) | 0.081000 (10) | 0.013 | |
O(22) | 0.52188 (2) | 0.44511 (3) | 0.250780 (10) | 0.011 | |
N(11) | 0.14219 (2) | 0.37539 (2) | 0.234300 (10) | 0.008 | |
N(12) | 0.46434 (2) | 0.35837 (3) | 0.158330 (10) | 0.008 | |
N(21) | −0.00504 (3) | 0.24524 (3) | 0.010100 (10) | 0.01 | |
N(22) | 0.29804 (3) | 0.19871 (3) | −0.061820 (10) | 0.012 | |
C(1) | 0.26649 (2) | 0.33329 (3) | 0.137210 (10) | 0.008 | |
C(2) | 0.18528 (3) | 0.25991 (3) | 0.025590 (10) | 0.008 | |
H(11) | −0.05872 | 0.20059 | −0.0691 | 0.019 | |
H(12) | −0.09554 | 0.3016 | 0.07155 | 0.02 | |
H(21) | 0.23363 | 0.15195 | −0.13755 | 0.021 | |
H(22) | 0.44262 | 0.20052 | −0.05163 | 0.021 | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O(11) | 0.00986 (6) | 0.02106 (7) | 0.00607 (4) | 0.00095 (5) | −0.00045 (4) | 0.00124 (4) |
O(12) | 0.00833 (5) | 0.01748 (7) | 0.00902 (5) | 0.00364 (5) | 0.00016 (4) | −0.00032 (4) |
O(21) | 0.00724 (5) | 0.02178 (8) | 0.01128 (5) | 0.00018 (5) | 0.00135 (4) | −0.00422 (5) |
O(22) | 0.00894 (5) | 0.01527 (7) | 0.00918 (5) | −0.00146 (5) | −0.00206 (4) | −0.00226 (4) |
N(11) | 0.00711 (5) | 0.01076 (6) | 0.00589 (4) | 0.00047 (4) | −0.00013 (4) | −0.00015 (3) |
N(12) | 0.00650 (5) | 0.01119 (6) | 0.00728 (4) | −0.00021 (4) | −0.00041 (4) | −0.00082 (4) |
N(21) | 0.00753 (6) | 0.01386 (7) | 0.00862 (5) | −0.00034 (5) | −0.00146 (4) | −0.00171 (4) |
N(22) | 0.00952 (6) | 0.01779 (8) | 0.00761 (5) | −0.00047 (6) | 0.00078 (4) | −0.00344 (5) |
C(1) | 0.00653 (6) | 0.01114 (6) | 0.00621 (5) | −0.00018 (5) | −0.00017 (4) | −0.00103 (4) |
C(2) | 0.00730 (6) | 0.00988 (6) | 0.00623 (5) | −0.00040 (5) | −0.00024 (4) | −0.00038 (4) |
H(11) | 0.0131 | 0.0296 | 0.0128 | −0.0075 | −0.0052 | −0.0017 |
H(12) | 0.0137 | 0.0326 | 0.0151 | 0.0046 | 0.0073 | 0.0013 |
H(21) | 0.02 | 0.0352 | 0.0089 | 0.0023 | −0.0004 | −0.0097 |
H(22) | 0.0086 | 0.0312 | 0.024 | 0.0023 | 0.0026 | −0.0057 |
Geometric parameters (Å, º) top
O(11)—N(11) | 1.2370 (2) | N(21)—H(11) | 1.0061 (2) |
O(12)—N(11) | 1.2391 (2) | N(21)—H(12) | 1.0064 (2) |
O(21)—N(12) | 1.2486 (2) | N(22)—C(2) | 1.3227 (2) |
O(22)—N(12) | 1.2464 (2) | N(22)—H(21) | 1.0061 (2) |
N(11)—C(1) | 1.4237 (2) | N(22)—H(22) | 1.0064 (2) |
N(12)—C(1) | 1.3976 (2) | C(1)—C(2) | 1.4532 (2) |
N(21)—C(2) | 1.3308 (2) | | |
| | | |
O(11)—N(11)—O(12) | 121.260 (18) | C(2)—N(22)—H(21) | 117.496 (19) |
O(11)—N(11)—C(1) | 120.268 (17) | C(2)—N(22)—H(22) | 120.274 (17) |
O(12)—N(11)—C(1) | 118.439 (15) | H(21)—N(22)—H(22) | 122.230 (18) |
O(21)—N(12)—O(22) | 120.938 (19) | N(11)—C(1)—N(12) | 116.397 (14) |
O(21)—N(12)—C(1) | 118.940 (15) | N(11)—C(1)—C(2) | 119.709 (15) |
O(22)—N(12)—C(1) | 120.045 (17) | N(12)—C(1)—C(2) | 123.840 (15) |
C(2)—N(21)—H(11) | 119.646 (18) | N(21)—C(2)—N(22) | 118.074 (18) |
C(2)—N(21)—H(12) | 120.328 (16) | N(21)—C(2)—C(1) | 120.811 (16) |
H(11)—N(21)—H(12) | 119.161 (18) | N(22)—C(2)—C(1) | 121.070 (17) |
Crystal data top
C8H6N12O12 | Z = 4 |
Mr = 438.23 | Dx = 2.08 Mg m−3 |
Monoclinic, P21/n | Synchrotron radiation, λ = ? Å |
a = 8.789 (1) Å | µ = 0.20 mm−1 |
b = 12.474 (1) Å | T = 100 K |
c = 13.279 (1) Å | Rectangular, colourless |
β = 106.578 (1)° | 0.31 × 0.26 × 0.24 mm |
V = 1395.31 (1) Å3 | |
Data collection top
Beamline E2; HASYLAB-DESY diffractometer | Rint = 2.9 |
rotation photographs scans | θmax = 33.6° |
486590 measured reflections | h = ?→? |
16427 independent reflections | k = ?→? |
14455 reflections with I > 3σ(I) | l = ?→? |
Refinement top
Refinement on F | 0 restraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.028 | w1 = 1/[s2(Fo)] |
wR(F2) = 0.033 | (Δ/σ)max < 0.001 |
S = 1.98 | Δρmax = 0.82 e Å−3 |
14455 reflections | Δρmin = −0.51 e Å−3 |
360 parameters | |
Crystal data top
C8H6N12O12 | V = 1395.31 (1) Å3 |
Mr = 438.23 | Z = 4 |
Monoclinic, P21/n | Synchrotron radiation, λ = ? Å |
a = 8.789 (1) Å | µ = 0.20 mm−1 |
b = 12.474 (1) Å | T = 100 K |
c = 13.279 (1) Å | 0.31 × 0.26 × 0.24 mm |
β = 106.578 (1)° | |
Data collection top
Beamline E2; HASYLAB-DESY diffractometer | 14455 reflections with I > 3σ(I) |
486590 measured reflections | Rint = 2.9 |
16427 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.028 | 0 restraints |
wR(F2) = 0.033 | All H-atom parameters refined |
S = 1.98 | Δρmax = 0.82 e Å−3 |
14455 reflections | Δρmin = −0.51 e Å−3 |
360 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O(1) | −0.08987 (3) | 0.61182 (2) | 0.35504 (3) | 0.02 | |
O(2) | −0.26363 (3) | 0.72388 (2) | 0.38327 (2) | 0.014 | |
O(3) | −0.34843 (3) | 0.73615 (2) | 0.15074 (2) | 0.014 | |
O(4) | −0.28990 (3) | 0.79812 (2) | 0.01228 (2) | 0.015 | |
O(5) | 0.07974 (3) | 1.11271 (2) | 0.11098 (2) | 0.013 | |
O(6) | 0.09800 (3) | 1.16082 (2) | 0.27229 (2) | 0.011 | |
O(7) | 0.30886 (3) | 0.94544 (2) | 0.51124 (2) | 0.018 | |
O(8) | 0.12322 (3) | 1.06521 (2) | 0.49096 (2) | 0.013 | |
O(9) | 0.46340 (3) | 0.88244 (2) | 0.27417 (2) | 0.014 | |
O(10) | 0.35068 (3) | 0.90223 (2) | 0.10622 (2) | 0.019 | |
O(11) | 0.09773 (3) | 0.67837 (2) | 0.03994 (2) | 0.016 | |
O(12) | 0.09723 (3) | 0.58507 (2) | 0.17845 (2) | 0.014 | |
N(1) | −0.14830 (3) | 0.70052 (2) | 0.35472 (2) | 0.011 | |
N(2) | −0.06949 (3) | 0.78652 (2) | 0.32188 (2) | 0.008 | |
N(3) | −0.28694 (3) | 0.80023 (2) | 0.10500 (2) | 0.009 | |
N(4) | −0.20831 (3) | 0.88574 (2) | 0.16283 (2) | 0.008 | |
N(5) | 0.04928 (3) | 1.10367 (2) | 0.19532 (2) | 0.008 | |
N(6) | −0.05252 (3) | 1.02319 (2) | 0.20331 (2) | 0.008 | |
N(7) | 0.18681 (3) | 0.98863 (2) | 0.46207 (2) | 0.01 | |
N(8) | 0.11037 (3) | 0.94578 (2) | 0.36423 (2) | 0.009 | |
N(9) | 0.35017 (3) | 0.89290 (2) | 0.19742 (2) | 0.011 | |
N(10) | 0.19820 (3) | 0.90273 (2) | 0.21599 (2) | 0.008 | |
N(11) | 0.08105 (3) | 0.66692 (2) | 0.12686 (2) | 0.01 | |
N(12) | 0.02713 (3) | 0.75811 (2) | 0.17128 (2) | 0.008 | |
C(1) | 0.06797 (3) | 0.76375 (2) | 0.28698 (2) | 0.008 | |
C(3) | −0.16053 (3) | 0.88079 (2) | 0.27894 (2) | 0.008 | |
C(5) | −0.08676 (3) | 0.93829 (2) | 0.12516 (2) | 0.007 | |
C(7) | −0.04681 (3) | 0.98132 (2) | 0.30786 (2) | 0.008 | |
C(9) | 0.18339 (3) | 0.86343 (2) | 0.31731 (2) | 0.008 | |
C(11) | 0.06223 (3) | 0.86242 (2) | 0.13295 (2) | 0.008 | |
H(1) | −0.13559 | 0.96918 | 0.0455 | 0.017 (2) | |
H(2) | 0.08777 | 0.85813 | 0.05725 | 0.023 (2) | |
H(3) | −0.26335 | 0.88575 | 0.30938 | 0.020 (2) | |
H(4) | −0.08608 | 1.04119 | 0.35502 | 0.019 (2) | |
H(5) | 0.29816 | 0.84247 | 0.37177 | 0.020 (2) | |
H(6) | 0.12363 | 0.68842 | 0.32005 | 0.025 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O(1) | 0.01760 (10) | 0.00910 (10) | 0.03170 (10) | −0.00050 (10) | 0.01080 (10) | 0.00480 (10) |
O(2) | 0.01351 (8) | 0.01450 (8) | 0.01492 (8) | −0.00420 (7) | 0.00814 (7) | −0.00039 (6) |
O(3) | 0.01352 (8) | 0.01426 (8) | 0.01308 (7) | −0.00684 (7) | 0.00491 (6) | −0.00238 (6) |
O(4) | 0.01774 (9) | 0.01681 (9) | 0.00729 (6) | −0.00497 (8) | 0.00149 (6) | −0.00252 (6) |
O(5) | 0.01409 (8) | 0.01268 (8) | 0.01037 (7) | −0.00161 (7) | 0.00538 (6) | 0.00197 (6) |
O(6) | 0.01162 (7) | 0.00852 (7) | 0.01292 (7) | −0.00201 (6) | 0.00350 (6) | −0.00295 (5) |
O(7) | 0.01700 (10) | 0.01940 (10) | 0.01250 (10) | 0.00250 (10) | −0.00600 (10) | −0.00130 (10) |
O(8) | 0.01482 (8) | 0.01395 (8) | 0.01068 (7) | −0.00360 (7) | 0.00480 (6) | −0.00526 (6) |
O(9) | 0.00665 (7) | 0.01383 (8) | 0.02086 (9) | 0.00032 (6) | 0.00270 (6) | −0.00260 (7) |
O(10) | 0.01482 (9) | 0.02605 (12) | 0.01743 (9) | −0.00334 (9) | 0.01066 (8) | −0.00164 (8) |
O(11) | 0.02250 (10) | 0.01200 (10) | 0.01500 (10) | 0.00120 (10) | 0.01070 (10) | −0.00280 (10) |
O(12) | 0.01546 (9) | 0.00687 (7) | 0.01665 (8) | 0.00160 (6) | 0.00279 (7) | 0.00057 (6) |
N(1) | 0.01046 (8) | 0.00963 (8) | 0.01109 (7) | −0.00279 (6) | 0.00357 (6) | 0.00119 (6) |
N(2) | 0.00792 (7) | 0.00817 (7) | 0.00844 (6) | −0.00056 (6) | 0.00287 (5) | 0.00173 (5) |
N(3) | 0.00796 (7) | 0.01045 (7) | 0.00791 (6) | −0.00190 (6) | 0.00082 (5) | −0.00144 (5) |
N(4) | 0.00662 (6) | 0.00872 (7) | 0.00693 (6) | −0.00108 (6) | 0.00096 (5) | −0.00049 (5) |
N(5) | 0.00786 (7) | 0.00651 (6) | 0.00938 (6) | 0.00003 (6) | 0.00249 (5) | 0.00042 (5) |
N(6) | 0.00836 (7) | 0.00638 (7) | 0.00737 (7) | −0.00041 (7) | 0.00191 (6) | 0.00012 (5) |
N(7) | 0.01094 (7) | 0.01034 (7) | 0.00641 (6) | −0.00282 (6) | 0.00069 (5) | −0.00056 (5) |
N(8) | 0.00760 (7) | 0.00992 (7) | 0.00683 (6) | 0.00026 (6) | 0.00009 (5) | −0.00186 (5) |
N(9) | 0.00801 (7) | 0.00915 (8) | 0.01560 (8) | −0.00124 (6) | 0.00566 (6) | −0.00197 (6) |
N(10) | 0.00607 (6) | 0.00860 (7) | 0.00861 (6) | −0.00055 (5) | 0.00229 (5) | −0.00035 (5) |
N(11) | 0.00905 (7) | 0.00694 (7) | 0.01216 (7) | 0.00028 (6) | 0.00298 (6) | −0.00159 (5) |
N(12) | 0.00850 (7) | 0.00611 (6) | 0.00763 (6) | 0.00027 (5) | 0.00232 (5) | −0.00013 (5) |
C(1) | 0.00729 (7) | 0.00715 (7) | 0.00785 (6) | 0.00001 (6) | 0.00142 (6) | 0.00102 (5) |
C(3) | 0.00675 (7) | 0.00841 (7) | 0.00728 (6) | −0.00045 (6) | 0.00211 (5) | −0.00039 (5) |
C(5) | 0.00758 (7) | 0.00726 (7) | 0.00642 (6) | 0.00008 (6) | 0.00112 (5) | 0.00051 (5) |
C(7) | 0.00725 (7) | 0.00782 (7) | 0.00719 (6) | −0.00020 (6) | 0.00207 (5) | −0.00078 (5) |
C(9) | 0.00628 (7) | 0.00804 (8) | 0.00795 (7) | 0.00006 (6) | 0.00073 (5) | 0.00021 (5) |
C(11) | 0.00787 (7) | 0.00713 (7) | 0.00721 (6) | −0.00024 (6) | 0.00244 (6) | −0.00003 (5) |
Geometric parameters (Å, º) top
O(1)—N(1) | 1.2193 (4) | N(4)—C(5) | 1.4581 (3) |
O(2)—N(1) | 1.2147 (3) | N(5)—N(6) | 1.3689 (3) |
O(3)—N(3) | 1.2195 (3) | N(6)—C(5) | 1.4528 (3) |
O(4)—N(3) | 1.2243 (3) | N(7)—N(8) | 1.3881 (3) |
O(5)—N(5) | 1.2288 (3) | N(8)—C(7) | 1.4405 (3) |
O(6)—N(5) | 1.2192 (3) | N(8)—C(9) | 1.4434 (3) |
O(7)—N(7) | 1.2115 (4) | N(10)—C(11) | 1.4646 (3) |
O(8)—N(7) | 1.2226 (3) | N(12)—C(11) | 1.4618 (3) |
O(9)—N(9) | 1.2113 (4) | C(1)—H(6) | 1.0920 (2) |
O(10)—N(9) | 1.2180 (3) | C(3)—H(3) | 1.0920 (2) |
O(11)—N(11) | 1.2126 (3) | C(5)—H(1) | 1.0920 (2) |
O(12)—N(11) | 1.2151 (3) | C(7)—H(4) | 1.0920 (2) |
N(2)—C(1) | 1.4403 (3) | C(9)—H(5) | 1.0920 (2) |
N(2)—C(3) | 1.4450 (3) | C(11)—H(2) | 1.0920 (2) |
N(3)—N(4) | 1.3792 (3) | | |
| | | |
O(1)—N(1)—O(2) | 127.21 (3) | N(7)—N(8)—C(9) | 121.46 (2) |
C(1)—N(2)—C(3) | 117.021 (19) | C(7)—N(8)—C(9) | 118.25 (2) |
O(3)—N(3)—O(4) | 126.98 (3) | O(9)—N(9)—O(10) | 127.71 (3) |
O(3)—N(3)—N(4) | 116.90 (2) | O(11)—N(11)—O(12) | 127.53 (3) |
O(4)—N(3)—N(4) | 116.10 (2) | N(2)—C(1)—H(6) | 111.159 (19) |
N(3)—N(4)—C(5) | 117.157 (19) | N(2)—C(3)—H(3) | 108.879 (19) |
O(5)—N(5)—O(6) | 126.50 (2) | N(4)—C(5)—N(6) | 96.047 (18) |
O(5)—N(5)—N(6) | 117.07 (2) | N(4)—C(5)—H(1) | 111.53 (2) |
O(6)—N(5)—N(6) | 116.41 (2) | N(6)—C(5)—H(1) | 112.26 (2) |
N(5)—N(6)—C(5) | 119.075 (19) | N(8)—C(7)—H(4) | 109.002 (19) |
O(7)—N(7)—O(8) | 126.31 (3) | N(8)—C(9)—H(5) | 108.971 (19) |
O(7)—N(7)—N(8) | 116.80 (2) | N(10)—C(11)—N(12) | 104.558 (19) |
O(8)—N(7)—N(8) | 116.88 (2) | N(10)—C(11)—H(2) | 111.835 (19) |
N(7)—N(8)—C(7) | 120.28 (2) | N(12)—C(11)—H(2) | 113.340 (19) |
Experimental details
| (FOX7) | (CL20) |
Crystal data |
Chemical formula | C2H4N4O4 | C8H6N12O12 |
Mr | 148.09 | 438.23 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/n |
Temperature (K) | 100 | 100 |
a, b, c (Å) | 6.922 (1), 6.501 (1), 11.262 (1) | 8.789 (1), 12.474 (1), 13.279 (1) |
β (°) | 90.485 (1) | 106.578 (1) |
V (Å3) | 506.77 | 1395.31 (1) |
Z | 4 | 4 |
Radiation type | Synchrotron, λ = ? Å | Synchrotron, λ = ? Å |
µ (mm−1) | 0.78 | 0.20 |
Crystal size (mm) | 0.27 × 0.25 × 0.22 | 0.31 × 0.26 × 0.24 |
|
Data collection |
Diffractometer | Beamline E2; HASYLAB-DESY diffractometer | Beamline E2; HASYLAB-DESY diffractometer |
Absorption correction | – | – |
No. of measured, independent and observed [I > 3σ(I)] reflections | 143788, 6093, 5329 | 486590, 16427, 14455 |
Rint | 2.7 | 2.9 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.021, 0.027, 2.05 | 0.028, 0.033, 1.98 |
No. of reflections | 5329 | 14455 |
No. of parameters | 184 | 360 |
H-atom treatment | All H-atom parameters refined | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.29, −0.36 | 0.82, −0.51 |
Selected geometric parameters (Å, º) for (FOX7) topO(11)—N(11) | 1.2370 (2) | N(21)—H(11) | 1.0061 (2) |
O(12)—N(11) | 1.2391 (2) | N(21)—H(12) | 1.0064 (2) |
O(21)—N(12) | 1.2486 (2) | N(22)—C(2) | 1.3227 (2) |
O(22)—N(12) | 1.2464 (2) | N(22)—H(21) | 1.0061 (2) |
N(11)—C(1) | 1.4237 (2) | N(22)—H(22) | 1.0064 (2) |
N(12)—C(1) | 1.3976 (2) | C(1)—C(2) | 1.4532 (2) |
N(21)—C(2) | 1.3308 (2) | | |
| | | |
O(11)—N(11)—O(12) | 121.260 (18) | C(2)—N(22)—H(21) | 117.496 (19) |
O(11)—N(11)—C(1) | 120.268 (17) | C(2)—N(22)—H(22) | 120.274 (17) |
O(12)—N(11)—C(1) | 118.439 (15) | H(21)—N(22)—H(22) | 122.230 (18) |
O(21)—N(12)—O(22) | 120.938 (19) | N(11)—C(1)—N(12) | 116.397 (14) |
O(21)—N(12)—C(1) | 118.940 (15) | N(11)—C(1)—C(2) | 119.709 (15) |
O(22)—N(12)—C(1) | 120.045 (17) | N(12)—C(1)—C(2) | 123.840 (15) |
C(2)—N(21)—H(11) | 119.646 (18) | N(21)—C(2)—N(22) | 118.074 (18) |
C(2)—N(21)—H(12) | 120.328 (16) | N(21)—C(2)—C(1) | 120.811 (16) |
H(11)—N(21)—H(12) | 119.161 (18) | N(22)—C(2)—C(1) | 121.070 (17) |
Selected geometric parameters (Å, º) for (CL20) topO(1)—N(1) | 1.2193 (4) | N(4)—C(5) | 1.4581 (3) |
O(2)—N(1) | 1.2147 (3) | N(5)—N(6) | 1.3689 (3) |
O(3)—N(3) | 1.2195 (3) | N(6)—C(5) | 1.4528 (3) |
O(4)—N(3) | 1.2243 (3) | N(7)—N(8) | 1.3881 (3) |
O(5)—N(5) | 1.2288 (3) | N(8)—C(7) | 1.4405 (3) |
O(6)—N(5) | 1.2192 (3) | N(8)—C(9) | 1.4434 (3) |
O(7)—N(7) | 1.2115 (4) | N(10)—C(11) | 1.4646 (3) |
O(8)—N(7) | 1.2226 (3) | N(12)—C(11) | 1.4618 (3) |
O(9)—N(9) | 1.2113 (4) | C(1)—H(6) | 1.0920 (2) |
O(10)—N(9) | 1.2180 (3) | C(3)—H(3) | 1.0920 (2) |
O(11)—N(11) | 1.2126 (3) | C(5)—H(1) | 1.0920 (2) |
O(12)—N(11) | 1.2151 (3) | C(7)—H(4) | 1.0920 (2) |
N(2)—C(1) | 1.4403 (3) | C(9)—H(5) | 1.0920 (2) |
N(2)—C(3) | 1.4450 (3) | C(11)—H(2) | 1.0920 (2) |
N(3)—N(4) | 1.3792 (3) | | |
| | | |
O(1)—N(1)—O(2) | 127.21 (3) | N(7)—N(8)—C(9) | 121.46 (2) |
C(1)—N(2)—C(3) | 117.021 (19) | C(7)—N(8)—C(9) | 118.25 (2) |
O(3)—N(3)—O(4) | 126.98 (3) | O(9)—N(9)—O(10) | 127.71 (3) |
O(3)—N(3)—N(4) | 116.90 (2) | O(11)—N(11)—O(12) | 127.53 (3) |
O(4)—N(3)—N(4) | 116.10 (2) | N(2)—C(1)—H(6) | 111.159 (19) |
N(3)—N(4)—C(5) | 117.157 (19) | N(2)—C(3)—H(3) | 108.879 (19) |
O(5)—N(5)—O(6) | 126.50 (2) | N(4)—C(5)—N(6) | 96.047 (18) |
O(5)—N(5)—N(6) | 117.07 (2) | N(4)—C(5)—H(1) | 111.53 (2) |
O(6)—N(5)—N(6) | 116.41 (2) | N(6)—C(5)—H(1) | 112.26 (2) |
N(5)—N(6)—C(5) | 119.075 (19) | N(8)—C(7)—H(4) | 109.002 (19) |
O(7)—N(7)—O(8) | 126.31 (3) | N(8)—C(9)—H(5) | 108.971 (19) |
O(7)—N(7)—N(8) | 116.80 (2) | N(10)—C(11)—N(12) | 104.558 (19) |
O(8)—N(7)—N(8) | 116.88 (2) | N(10)—C(11)—H(2) | 111.835 (19) |
N(7)—N(8)—C(7) | 120.28 (2) | N(12)—C(11)—H(2) | 113.340 (19) |