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Extremely accurate X-ray data were obtained for the explosive RDX (hexahydro-1,3,5-trinitro-1,3,5-triazine) at three different temperatures (20, 120 and 298 K). Collected reflections were integrated using the latest version of the program VIIPP which uses separate Kα1/Kα2 contributions to the profile fitting during integration. For each temperature both anharmonic and harmonic descriptions of the atomic thermal motion were utilized in the model refinements along with the multipole expansion of the electron density. H atoms were refined anisotropically and agree well with a previous neutron study. Topological analysis [Bader (1990). Atoms in Molecules: A Quantum Theory. The International Series of Monographs of Chemistry, edited by J. Halpern & M. L. H. Green. Oxford: Clarendon Press] of the attained electron density followed. For 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane (HMX), old data collected at 20 and 120 K were re-integrated with the new version of VIIPP and refined in the same manner as for RDX. In both cases theoretical structure factors were also calculated based on the 20 K structures, and employed in comparison multipole refinements for the atoms at rest. Limiting the refinement to a harmonic model of the atomic displacements may result in a biased and erroneous electron density, especially when atomic vibrations are significant (as in RDX) and at temperatures higher than obtained by using liquid helium. Given the similarity of the two compounds the effects of anharmonic motion are strikingly more severe in the case of RDX. Our study reinforces the conclusion of Meindl et al. [Acta Cryst. (2010), A66, 362–371] that in certain cases it is necessary to include anharmonic term(s) of the probability density function (or temperature factor) in order to obtain a meaningful electron density suitable for topological analysis, even for compact (high-density) light-atom structures. For RDX it was observed that the oxygen lone-pair concentrations of electrons are located close to perpendicular to the N—O bond vectors, which is typical for explosive materials. Conjugation of the electron density in the —N—NO2 fragment has been established based on the topological bond orders. Nine moderately strong hydrogen bonds and nine N—N, O—N and O—O bonding interactions were found and described. The RDX molecular electronic energy per mole is 4.02–4.04 a.u., very close to the reported value for HMX.
Keywords: explosives; charge densities; anharmonic thermal motion; variable-temperature X-ray diffraction; anisotropic hydrogen atoms.
Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S0108767310052219/sh5121sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S0108767310052219/sh5121RDX20KAnharmonicsup2.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108767310052219/sh5121RDX20KHarmonicsup3.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108767310052219/sh5121RDX120KAnharmonicsup4.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108767310052219/sh5121RDX120KHarmonicsup5.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108767310052219/sh5121RDX298KAnharmonicsup6.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108767310052219/sh5121RDX298KHarmonicsup7.hkl |
 | Portable Document Format (PDF) file https://doi.org/10.1107/S0108767310052219/sh5121sup8.pdf |
Computing details top
For all compounds, data collection: CrystalClear,(2005); cell refinement: Otwinowski & Minor (1997); data reduction: Zhurov et al.,(2005); program(s) used to solve structure: Sheldrick (1997); program(s) used to refine structure: Volkov et al., (2006); molecular graphics: Volkov et al., (2006); software used to prepare material for publication: Volkov et al., (2006).
(RDX20KAnharmonic) top
Crystal data top
| C3H6N6O6 | F(000) = 912.0 |
| Mr = 222.14 | Dx = 1.868 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 120142 reflections |
| a = 11.3790 (2) Å | θ = 3.1–70.0° |
| b = 10.5694 (2) Å | µ = 0.18 mm−1 |
| c = 13.1314 (2) Å | T = 20 K |
| V = 1579.30 (5) Å3 | Pyramid, colorless |
| Z = 8 | 0.23 × 0.23 × 0.23 mm |
Data collection top
| Rigaku R-axis Rapid diffractometer | Rint = 0.019 |
| w scans | θmax = 70.0° |
| 120142 measured reflections | h = −28→28 |
| 10651 independent reflections | k = −15→21 |
| 8057 reflections with I > 3σ, non−overlapped & non−partial reflections | l = −34→34 |
Refinement top
| Refinement on F2 | All H-atom parameters refined |
| R[F2 > 2σ(F2)] = 0.015 | w2 = q/[s2(Fo2) + (0.006 P)2 + 0.008 P + 0.00 + 0.00 sin(th)]
where P = (1.0000 Fo2 + 0.0000 Fc2) q = 1.0 |
| wR(F2) = 0.010 | (Δ/σ)max < 0.001 |
| S = 0.90 | Δρmax = 0.19 e Å−3 |
| 8057 reflections | Δρmin = −0.17 e Å−3 |
| 754 parameters |
Crystal data top
| C3H6N6O6 | V = 1579.30 (5) Å3 |
| Mr = 222.14 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα radiation |
| a = 11.3790 (2) Å | µ = 0.18 mm−1 |
| b = 10.5694 (2) Å | T = 20 K |
| c = 13.1314 (2) Å | 0.23 × 0.23 × 0.23 mm |
Data collection top
| Rigaku R-axis Rapid diffractometer | 8057 reflections with I > 3σ, non−overlapped & non−partial reflections |
| 120142 measured reflections | Rint = 0.019 |
| 10651 independent reflections |
Refinement top
| R[F2 > 2σ(F2)] = 0.015 | 754 parameters |
| wR(F2) = 0.010 | All H-atom parameters refined |
| S = 0.90 | Δρmax = 0.19 e Å−3 |
| 8057 reflections | Δρmin = −0.17 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O(1) | 0.56754 (4) | 0.43545 (7) | 0.26809 (3) | 0.007 | |
| O(2) | 0.59333 (4) | 0.23619 (7) | 0.22993 (4) | 0.008 | |
| O(3) | 0.46378 (4) | 0.13223 (7) | −0.02745 (3) | 0.009 | |
| O(4) | 0.35040 (4) | 0.25476 (7) | −0.11767 (3) | 0.008 | |
| O(5) | 0.31937 (4) | 0.53406 (7) | −0.07311 (3) | 0.008 | |
| O(6) | 0.43403 (4) | 0.60542 (7) | 0.04655 (4) | 0.008 | |
| N(1) | 0.43458 (4) | 0.33659 (7) | 0.17429 (3) | 0.005 | |
| N(2) | 0.31745 (4) | 0.23613 (6) | 0.05024 (3) | 0.005 | |
| N(3) | 0.29626 (4) | 0.46118 (7) | 0.08586 (3) | 0.005 | |
| N(4) | 0.53670 (3) | 0.33581 (5) | 0.22798 (2) | 0.005 | |
| N(5) | 0.38357 (3) | 0.20812 (4) | −0.03739 (2) | 0.005 | |
| N(6) | 0.35568 (3) | 0.53636 (4) | 0.01446 (2) | 0.005 | |
| C(1) | 0.35515 (3) | 0.44488 (5) | 0.18351 (2) | 0.005 | |
| C(2) | 0.37737 (3) | 0.21703 (5) | 0.14695 (2) | 0.005 | |
| C(3) | 0.23957 (3) | 0.34644 (4) | 0.04640 (3) | 0.005 | |
| H(1A) | 0.4032 (9) | 0.5282 (11) | 0.2040 (7) | 0.014 | |
| H(1B) | 0.2869 (9) | 0.4241 (9) | 0.2388 (7) | 0.016 | |
| H(2A) | 0.4394 (10) | 0.1427 (11) | 0.1418 (7) | 0.018 | |
| H(2B) | 0.3104 (9) | 0.1948 (9) | 0.2034 (7) | 0.016 | |
| H(3A) | 0.2085 (9) | 0.3617 (9) | −0.0285 (8) | 0.014 | |
| H(3B) | 0.1676 (8) | 0.3258 (8) | 0.0973 (7) | 0.013 |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O(1) | 0.00658 (4) | 0.00784 (7) | 0.00717 (3) | −0.00140 (4) | −0.00200 (3) | −0.00121 (4) |
| O(2) | 0.00656 (4) | 0.00766 (8) | 0.01082 (4) | 0.00191 (5) | −0.00243 (3) | 0.00074 (5) |
| O(3) | 0.00777 (5) | 0.00927 (8) | 0.00947 (4) | 0.00320 (5) | 0.00208 (3) | −0.00059 (4) |
| O(4) | 0.00991 (5) | 0.01081 (8) | 0.00405 (3) | 0.00061 (5) | 0.00063 (3) | 0.00035 (4) |
| O(5) | 0.00967 (5) | 0.00898 (8) | 0.00541 (3) | 0.00004 (5) | 0.00047 (3) | 0.00171 (4) |
| O(6) | 0.00683 (5) | 0.00713 (8) | 0.01081 (5) | −0.00247 (5) | 0.00099 (3) | −0.00015 (5) |
| N(1) | 0.00480 (4) | 0.00465 (7) | 0.00627 (4) | 0.00025 (4) | −0.00196 (3) | −0.00042 (4) |
| N(2) | 0.00490 (4) | 0.00520 (7) | 0.00386 (3) | 0.00036 (4) | −0.00019 (2) | −0.00048 (4) |
| N(3) | 0.00475 (4) | 0.00495 (7) | 0.00479 (3) | −0.00030 (4) | −0.00060 (2) | 0.00042 (4) |
| N(4) | 0.00430 (3) | 0.00581 (7) | 0.00467 (3) | −0.00021 (4) | −0.00092 (2) | 0.00044 (3) |
| N(5) | 0.00524 (4) | 0.00584 (6) | 0.00456 (3) | −0.00005 (4) | 0.00084 (2) | −0.00065 (3) |
| N(6) | 0.00493 (4) | 0.00495 (6) | 0.00584 (3) | 0.00012 (4) | 0.00072 (2) | 0.00057 (3) |
| C(1) | 0.00573 (4) | 0.00545 (7) | 0.00499 (3) | 0.00057 (4) | −0.00073 (3) | −0.00070 (4) |
| C(2) | 0.00638 (4) | 0.00490 (7) | 0.00475 (3) | −0.00047 (4) | −0.00086 (3) | 0.00037 (4) |
| C(3) | 0.00403 (4) | 0.00580 (7) | 0.00508 (3) | −0.00012 (4) | −0.00031 (3) | −0.00020 (4) |
| H(1A) | 0.013 (3) | 0.011 (4) | 0.017 (3) | −0.001 (2) | −0.0058 (19) | −0.003 (2) |
| H(1B) | 0.014 (3) | 0.021 (3) | 0.012 (3) | 0.002 (2) | 0.002 (2) | 0.001 (2) |
| H(2A) | 0.021 (4) | 0.020 (5) | 0.012 (3) | −0.004 (3) | −0.003 (2) | −0.001 (2) |
| H(2B) | 0.020 (3) | 0.016 (3) | 0.012 (3) | −0.006 (2) | 0.000 (2) | 0.0029 (19) |
| H(3A) | 0.014 (3) | 0.016 (3) | 0.013 (3) | −0.0004 (19) | −0.000 (2) | −0.002 (2) |
| H(3B) | 0.010 (3) | 0.012 (3) | 0.017 (3) | −0.0027 (19) | 0.005 (2) | −0.0010 (19) |
Geometric parameters (Å, º) top
| O(1)—N(4) | 1.2288 (7) | N(2)—C(3) | 1.4654 (7) |
| O(2)—N(4) | 1.2347 (8) | N(3)—N(6) | 1.4027 (6) |
| O(3)—N(5) | 1.2220 (6) | N(3)—C(1) | 1.4570 (5) |
| O(4)—N(5) | 1.2234 (5) | N(3)—C(3) | 1.4681 (7) |
| O(5)—N(6) | 1.2220 (5) | C(1)—H(1A) | 1.070 (12) |
| O(6)—N(6) | 1.2270 (6) | C(1)—H(1B) | 1.085 (10) |
| N(1)—N(4) | 1.3592 (5) | C(2)—H(2A) | 1.059 (13) |
| N(1)—C(1) | 1.4634 (8) | C(2)—H(2B) | 1.089 (11) |
| N(1)—C(2) | 1.4661 (8) | C(3)—H(3A) | 1.058 (11) |
| N(2)—N(5) | 1.4063 (5) | C(3)—H(3B) | 1.079 (10) |
| N(2)—C(2) | 1.4555 (5) | ||
| N(4)—N(1)—C(1) | 119.33 (5) | N(1)—C(1)—N(3) | 107.68 (4) |
| N(4)—N(1)—C(2) | 120.09 (6) | N(1)—C(1)—H(1A) | 110.4 (5) |
| C(1)—N(1)—C(2) | 114.85 (4) | N(1)—C(1)—H(1B) | 109.8 (5) |
| N(5)—N(2)—C(2) | 115.73 (4) | N(3)—C(1)—H(1A) | 111.0 (5) |
| N(5)—N(2)—C(3) | 117.57 (4) | N(3)—C(1)—H(1B) | 106.5 (5) |
| C(2)—N(2)—C(3) | 115.07 (4) | H(1A)—C(1)—H(1B) | 111.3 (7) |
| N(6)—N(3)—C(1) | 115.70 (4) | N(1)—C(2)—N(2) | 107.58 (4) |
| N(6)—N(3)—C(3) | 116.34 (4) | N(1)—C(2)—H(2A) | 111.1 (5) |
| C(1)—N(3)—C(3) | 114.52 (5) | N(1)—C(2)—H(2B) | 109.3 (5) |
| O(1)—N(4)—O(2) | 124.95 (5) | N(2)—C(2)—H(2A) | 111.1 (5) |
| O(1)—N(4)—N(1) | 117.47 (6) | N(2)—C(2)—H(2B) | 107.2 (5) |
| O(2)—N(4)—N(1) | 117.53 (6) | H(2A)—C(2)—H(2B) | 110.5 (7) |
| O(3)—N(5)—O(4) | 125.94 (4) | N(2)—C(3)—N(3) | 112.29 (4) |
| O(3)—N(5)—N(2) | 116.77 (4) | N(2)—C(3)—H(3A) | 110.9 (5) |
| O(4)—N(5)—N(2) | 117.08 (5) | N(2)—C(3)—H(3B) | 106.1 (5) |
| O(5)—N(6)—O(6) | 125.50 (5) | N(3)—C(3)—H(3A) | 110.4 (5) |
| O(5)—N(6)—N(3) | 117.05 (5) | N(3)—C(3)—H(3B) | 106.4 (5) |
| O(6)—N(6)—N(3) | 117.24 (4) | H(3A)—C(3)—H(3B) | 110.7 (7) |
(RDX20KHarmonic) top
Crystal data top
| C3H6N6O6 | F(000) = 912.0 |
| Mr = 222.14 | Dx = 1.868 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 120142 reflections |
| a = 11.3790 (2) Å | θ = 3.1–70.0° |
| b = 10.5694 (2) Å | µ = 0.18 mm−1 |
| c = 13.1314 (2) Å | T = 20 K |
| V = 1579.30 (5) Å3 | Pyramid, colorless |
| Z = 8 | 0.23 × 0.23 × 0.23 mm |
Data collection top
| Rigaku R-axis Rapid diffractometer | Rint = 0.019 |
| w scans | θmax = 70.0° |
| 120142 measured reflections | h = −28→28 |
| 10651 independent reflections | k = −15→21 |
| 8057 reflections with I > 3σ, non−overlapped & non−partial reflections | l = −34→34 |
Refinement top
| Refinement on F2 | All H-atom parameters refined |
| R[F2 > 2σ(F2)] = 0.015 | w2 = q/[s2(Fo2) + (0.006 P)2 + 0.012 P + 0.00 + 0.00 sin(th)]
where P = (1.0000 Fo2 + 0.0000 Fc2) q = 1.0 |
| wR(F2) = 0.011 | (Δ/σ)max < 0.001 |
| S = 0.86 | Δρmax = 0.19 e Å−3 |
| 8057 reflections | Δρmin = −0.20 e Å−3 |
| 604 parameters |
Crystal data top
| C3H6N6O6 | V = 1579.30 (5) Å3 |
| Mr = 222.14 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα radiation |
| a = 11.3790 (2) Å | µ = 0.18 mm−1 |
| b = 10.5694 (2) Å | T = 20 K |
| c = 13.1314 (2) Å | 0.23 × 0.23 × 0.23 mm |
Data collection top
| Rigaku R-axis Rapid diffractometer | 8057 reflections with I > 3σ, non−overlapped & non−partial reflections |
| 120142 measured reflections | Rint = 0.019 |
| 10651 independent reflections |
Refinement top
| R[F2 > 2σ(F2)] = 0.015 | 604 parameters |
| wR(F2) = 0.011 | All H-atom parameters refined |
| S = 0.86 | Δρmax = 0.19 e Å−3 |
| 8057 reflections | Δρmin = −0.20 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O(1) | 0.567533 (15) | 0.43518 (2) | 0.267970 (12) | 0.007 | |
| O(2) | 0.593197 (16) | 0.23647 (2) | 0.229961 (13) | 0.008 | |
| O(3) | 0.463641 (17) | 0.13247 (2) | −0.027480 (13) | 0.009 | |
| O(4) | 0.350573 (16) | 0.25460 (2) | −0.117490 (11) | 0.008 | |
| O(5) | 0.319494 (16) | 0.53412 (2) | −0.072786 (11) | 0.008 | |
| O(6) | 0.433891 (16) | 0.60516 (2) | 0.046596 (13) | 0.008 | |
| N(1) | 0.434558 (14) | 0.33655 (2) | 0.174315 (11) | 0.005 | |
| N(2) | 0.317528 (13) | 0.236081 (19) | 0.050244 (10) | 0.005 | |
| N(3) | 0.296262 (13) | 0.46114 (2) | 0.085876 (10) | 0.005 | |
| N(4) | 0.536675 (11) | 0.335765 (17) | 0.227919 (9) | 0.005 | |
| N(5) | 0.383556 (12) | 0.208053 (16) | −0.037389 (9) | 0.005 | |
| N(6) | 0.355713 (12) | 0.536468 (16) | 0.014473 (9) | 0.005 | |
| C(1) | 0.355164 (14) | 0.444755 (19) | 0.183464 (10) | 0.005 | |
| C(2) | 0.377369 (14) | 0.217061 (19) | 0.146953 (10) | 0.005 | |
| C(3) | 0.239662 (12) | 0.346451 (17) | 0.046408 (10) | 0.005 | |
| H(1A) | 0.4028 (10) | 0.5281 (12) | 0.2041 (8) | 0.012 | |
| H(1B) | 0.2868 (9) | 0.4240 (10) | 0.2390 (8) | 0.015 | |
| H(2A) | 0.4392 (11) | 0.1428 (12) | 0.1420 (8) | 0.016 | |
| H(2B) | 0.3106 (10) | 0.1949 (10) | 0.2035 (8) | 0.016 | |
| H(3A) | 0.2083 (10) | 0.3618 (10) | −0.0283 (9) | 0.013 | |
| H(3B) | 0.1678 (9) | 0.3257 (9) | 0.0971 (8) | 0.012 |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O(1) | 0.00650 (5) | 0.00785 (8) | 0.00721 (4) | −0.00133 (5) | −0.00201 (3) | −0.00118 (4) |
| O(2) | 0.00651 (5) | 0.00768 (8) | 0.01081 (5) | 0.00179 (5) | −0.00246 (3) | 0.00071 (5) |
| O(3) | 0.00782 (5) | 0.00929 (9) | 0.00935 (5) | 0.00314 (5) | 0.00210 (3) | −0.00060 (5) |
| O(4) | 0.00986 (5) | 0.01079 (8) | 0.00408 (3) | 0.00068 (5) | 0.00069 (3) | 0.00030 (4) |
| O(5) | 0.00965 (5) | 0.00888 (8) | 0.00547 (4) | −0.00005 (5) | 0.00049 (3) | 0.00172 (4) |
| O(6) | 0.00689 (5) | 0.00714 (8) | 0.01075 (5) | −0.00244 (5) | 0.00100 (4) | −0.00009 (5) |
| N(1) | 0.00481 (4) | 0.00466 (7) | 0.00626 (4) | 0.00027 (4) | −0.00195 (3) | −0.00042 (4) |
| N(2) | 0.00490 (4) | 0.00518 (7) | 0.00386 (3) | 0.00034 (4) | −0.00018 (3) | −0.00047 (4) |
| N(3) | 0.00475 (4) | 0.00494 (7) | 0.00479 (3) | −0.00032 (4) | −0.00061 (3) | 0.00040 (4) |
| N(4) | 0.00429 (4) | 0.00574 (7) | 0.00469 (3) | −0.00021 (4) | −0.00094 (2) | 0.00041 (3) |
| N(5) | 0.00523 (4) | 0.00586 (7) | 0.00455 (3) | −0.00003 (4) | 0.00085 (2) | −0.00064 (3) |
| N(6) | 0.00493 (4) | 0.00495 (6) | 0.00583 (3) | 0.00011 (4) | 0.00071 (2) | 0.00056 (3) |
| C(1) | 0.00575 (4) | 0.00543 (7) | 0.00499 (4) | 0.00054 (4) | −0.00073 (3) | −0.00071 (4) |
| C(2) | 0.00642 (5) | 0.00487 (7) | 0.00476 (4) | −0.00047 (4) | −0.00087 (3) | 0.00039 (4) |
| C(3) | 0.00403 (4) | 0.00583 (7) | 0.00508 (4) | −0.00012 (4) | −0.00031 (3) | −0.00018 (4) |
| H(1A) | 0.011 (3) | 0.009 (4) | 0.016 (3) | −0.002 (3) | −0.006 (2) | −0.003 (2) |
| H(1B) | 0.013 (3) | 0.020 (3) | 0.012 (3) | 0.002 (2) | 0.002 (2) | 0.002 (2) |
| H(2A) | 0.019 (4) | 0.018 (4) | 0.012 (3) | −0.002 (3) | −0.003 (2) | −0.001 (2) |
| H(2B) | 0.021 (4) | 0.016 (3) | 0.012 (3) | −0.005 (2) | 0.000 (2) | 0.003 (2) |
| H(3A) | 0.014 (3) | 0.014 (3) | 0.011 (3) | −0.001 (2) | 0.000 (2) | −0.002 (2) |
| H(3B) | 0.009 (3) | 0.011 (3) | 0.016 (3) | −0.002 (2) | 0.006 (2) | −0.001 (2) |
Geometric parameters (Å, º) top
| O(1)—N(4) | 1.2263 (3) | N(2)—C(3) | 1.4658 (2) |
| O(2)—N(4) | 1.2312 (3) | N(3)—N(6) | 1.4038 (2) |
| O(3)—N(5) | 1.2189 (2) | N(3)—C(1) | 1.4565 (2) |
| O(4)—N(5) | 1.2203 (2) | N(3)—C(3) | 1.4673 (2) |
| O(5)—N(6) | 1.2180 (2) | C(1)—H(1A) | 1.069 (12) |
| O(6)—N(6) | 1.2233 (2) | C(1)—H(1B) | 1.089 (11) |
| N(1)—N(4) | 1.3586 (2) | C(2)—H(2A) | 1.056 (13) |
| N(1)—C(1) | 1.4624 (3) | C(2)—H(2B) | 1.088 (11) |
| N(1)—C(2) | 1.4654 (3) | C(3)—H(3A) | 1.056 (12) |
| N(2)—N(5) | 1.4059 (2) | C(3)—H(3B) | 1.077 (11) |
| N(2)—C(2) | 1.4549 (2) | ||
| N(4)—N(1)—C(1) | 119.379 (17) | N(1)—C(1)—N(3) | 107.759 (13) |
| N(4)—N(1)—C(2) | 120.105 (18) | N(1)—C(1)—H(1A) | 110.6 (6) |
| C(1)—N(1)—C(2) | 114.821 (14) | N(1)—C(1)—H(1B) | 109.8 (5) |
| N(5)—N(2)—C(2) | 115.799 (14) | N(3)—C(1)—H(1A) | 111.0 (6) |
| N(5)—N(2)—C(3) | 117.557 (14) | N(3)—C(1)—H(1B) | 106.6 (5) |
| C(2)—N(2)—C(3) | 115.016 (14) | H(1A)—C(1)—H(1B) | 111.0 (8) |
| N(6)—N(3)—C(1) | 115.680 (14) | N(1)—C(2)—N(2) | 107.623 (15) |
| N(6)—N(3)—C(3) | 116.370 (13) | N(1)—C(2)—H(2A) | 111.1 (6) |
| C(1)—N(3)—C(3) | 114.489 (16) | N(1)—C(2)—H(2B) | 109.2 (5) |
| O(1)—N(4)—O(2) | 124.850 (17) | N(2)—C(2)—H(2A) | 111.1 (6) |
| O(1)—N(4)—N(1) | 117.508 (18) | N(2)—C(2)—H(2B) | 107.4 (5) |
| O(2)—N(4)—N(1) | 117.599 (19) | H(2A)—C(2)—H(2B) | 110.3 (8) |
| O(3)—N(5)—O(4) | 125.886 (16) | N(2)—C(3)—N(3) | 112.337 (13) |
| O(3)—N(5)—N(2) | 116.763 (15) | N(2)—C(3)—H(3A) | 111.0 (6) |
| O(4)—N(5)—N(2) | 117.143 (16) | N(2)—C(3)—H(3B) | 106.0 (5) |
| O(5)—N(6)—O(6) | 125.632 (18) | N(3)—C(3)—H(3A) | 110.4 (6) |
| O(5)—N(6)—N(3) | 116.985 (17) | N(3)—C(3)—H(3B) | 106.5 (5) |
| O(6)—N(6)—N(3) | 117.176 (14) | H(3A)—C(3)—H(3B) | 110.4 (8) |
(RDX120KAnharmonic) top
Crystal data top
| C3H6N6O6 | F(000) = 912.0 |
| Mr = 222.14 | Dx = 1.847 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 173199 reflections |
| a = 11.4425 (3) Å | θ = 3.0–66.8° |
| b = 10.6106 (3) Å | µ = 0.18 mm−1 |
| c = 13.1558 (4) Å | T = 120 K |
| V = 1597.27 (8) Å3 | Prism, colorless |
| Z = 8 | 0.29 × 0.29 × 0.17 mm |
Data collection top
| Rigaku R-axis Rapid diffractometer | Rint = 0.016 |
| w scans | θmax = 66.8° |
| 173199 measured reflections | h = −29→29 |
| 12304 independent reflections | k = −21→22 |
| 7986 reflections with I > 3σ, non−overlapped & non−partial reflections | l = −32→33 |
Refinement top
| Refinement on F2 | All H-atom parameters refined |
| R[F2 > 2σ(F2)] = 0.017 | w2 = q/[s2(Fo2) + (0.008 P)2 + 0.012 P + 0.00 + 0.00 sin(th)]
where P = (1.0000 Fo2 + 0.0000 Fc2) q = 1.0 |
| wR(F2) = 0.013 | (Δ/σ)max < 0.001 |
| S = 0.85 | Δρmax = 0.14 e Å−3 |
| 7986 reflections | Δρmin = −0.15 e Å−3 |
| 754 parameters |
Crystal data top
| C3H6N6O6 | V = 1597.27 (8) Å3 |
| Mr = 222.14 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα radiation |
| a = 11.4425 (3) Å | µ = 0.18 mm−1 |
| b = 10.6106 (3) Å | T = 120 K |
| c = 13.1558 (4) Å | 0.29 × 0.29 × 0.17 mm |
Data collection top
| Rigaku R-axis Rapid diffractometer | 7986 reflections with I > 3σ, non−overlapped & non−partial reflections |
| 173199 measured reflections | Rint = 0.016 |
| 12304 independent reflections |
Refinement top
| R[F2 > 2σ(F2)] = 0.017 | 754 parameters |
| wR(F2) = 0.013 | All H-atom parameters refined |
| S = 0.85 | Δρmax = 0.14 e Å−3 |
| 7986 reflections | Δρmin = −0.15 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O(1) | 0.56779 (6) | 0.43448 (10) | 0.26715 (6) | 0.016 | |
| O(2) | 0.59319 (7) | 0.23607 (11) | 0.22893 (8) | 0.020 | |
| O(3) | 0.46496 (8) | 0.13401 (11) | −0.02697 (8) | 0.022 | |
| O(4) | 0.35083 (8) | 0.25419 (11) | −0.11663 (6) | 0.020 | |
| O(5) | 0.31818 (9) | 0.53209 (11) | −0.07236 (6) | 0.020 | |
| O(6) | 0.43264 (8) | 0.60385 (10) | 0.04639 (9) | 0.021 | |
| N(1) | 0.43501 (5) | 0.33559 (7) | 0.17474 (5) | 0.012 | |
| N(2) | 0.31848 (5) | 0.23515 (7) | 0.05082 (4) | 0.011 | |
| N(3) | 0.29687 (5) | 0.45953 (7) | 0.08642 (5) | 0.011 | |
| N(4) | 0.53689 (4) | 0.33517 (6) | 0.22735 (3) | 0.012 | |
| N(5) | 0.38436 (4) | 0.20824 (5) | −0.03662 (4) | 0.013 | |
| N(6) | 0.35495 (4) | 0.53481 (5) | 0.01475 (4) | 0.014 | |
| C(1) | 0.35606 (5) | 0.44367 (6) | 0.18357 (4) | 0.013 | |
| C(2) | 0.37830 (5) | 0.21644 (6) | 0.14727 (4) | 0.012 | |
| C(3) | 0.24065 (4) | 0.34488 (5) | 0.04730 (4) | 0.011 | |
| H(1A) | 0.4039 (11) | 0.5258 (13) | 0.2042 (9) | 0.033 | |
| H(1B) | 0.2898 (11) | 0.4224 (12) | 0.2385 (9) | 0.024 | |
| H(2A) | 0.4384 (12) | 0.1427 (12) | 0.1432 (9) | 0.031 | |
| H(2B) | 0.3110 (11) | 0.1960 (12) | 0.2033 (9) | 0.026 | |
| H(3A) | 0.2093 (10) | 0.3601 (11) | −0.0291 (10) | 0.023 | |
| H(3B) | 0.1680 (10) | 0.3255 (10) | 0.0986 (9) | 0.022 |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O(1) | 0.01450 (6) | 0.02064 (9) | 0.01432 (6) | −0.00434 (6) | −0.00423 (5) | −0.00132 (7) |
| O(2) | 0.01466 (7) | 0.01982 (10) | 0.02444 (10) | 0.00307 (7) | −0.00603 (6) | 0.00401 (8) |
| O(3) | 0.01946 (8) | 0.02176 (11) | 0.02420 (11) | 0.00557 (8) | 0.00734 (8) | −0.00299 (9) |
| O(4) | 0.02442 (9) | 0.02653 (11) | 0.00917 (6) | −0.00131 (8) | 0.00307 (6) | −0.00128 (7) |
| O(5) | 0.02521 (10) | 0.02060 (11) | 0.01483 (7) | 0.00336 (8) | 0.00455 (6) | 0.00574 (7) |
| O(6) | 0.01650 (7) | 0.01493 (10) | 0.03068 (12) | −0.00382 (7) | 0.00626 (8) | 0.00006 (9) |
| N(1) | 0.01123 (5) | 0.01137 (7) | 0.01317 (6) | −0.00015 (5) | −0.00399 (4) | −0.00043 (5) |
| N(2) | 0.01044 (5) | 0.01246 (7) | 0.00891 (5) | −0.00099 (4) | 0.00025 (4) | −0.00121 (5) |
| N(3) | 0.00990 (5) | 0.01205 (7) | 0.01184 (6) | 0.00020 (5) | −0.00063 (4) | 0.00120 (5) |
| N(4) | 0.01028 (4) | 0.01586 (7) | 0.01042 (5) | −0.00123 (4) | −0.00226 (3) | 0.00216 (5) |
| N(5) | 0.01334 (5) | 0.01475 (7) | 0.01152 (5) | −0.00196 (5) | 0.00337 (4) | −0.00278 (5) |
| N(6) | 0.01249 (5) | 0.01175 (7) | 0.01685 (6) | 0.00188 (5) | 0.00426 (4) | 0.00266 (5) |
| C(1) | 0.01301 (6) | 0.01258 (8) | 0.01230 (6) | 0.00061 (5) | −0.00197 (4) | −0.00224 (5) |
| C(2) | 0.01463 (6) | 0.01083 (7) | 0.01094 (6) | −0.00141 (5) | −0.00177 (4) | 0.00122 (5) |
| C(3) | 0.00824 (4) | 0.01487 (7) | 0.01087 (5) | −0.00064 (4) | −0.00047 (4) | −0.00028 (5) |
| H(1A) | 0.035 (5) | 0.029 (6) | 0.036 (4) | 0.005 (4) | −0.006 (3) | 0.001 (3) |
| H(1B) | 0.021 (4) | 0.034 (4) | 0.019 (3) | 0.006 (3) | 0.003 (3) | −0.002 (3) |
| H(2A) | 0.031 (5) | 0.030 (5) | 0.033 (4) | −0.001 (3) | −0.009 (3) | −0.007 (3) |
| H(2B) | 0.026 (4) | 0.031 (4) | 0.021 (3) | −0.015 (3) | 0.007 (3) | −0.000 (3) |
| H(3A) | 0.022 (3) | 0.029 (4) | 0.017 (4) | −0.001 (2) | −0.003 (3) | 0.003 (3) |
| H(3B) | 0.017 (3) | 0.027 (3) | 0.023 (4) | −0.004 (2) | 0.005 (3) | 0.002 (2) |
Geometric parameters (Å, º) top
| O(1)—N(4) | 1.2286 (10) | N(2)—C(3) | 1.4666 (8) |
| O(2)—N(4) | 1.2333 (11) | N(3)—N(6) | 1.4031 (8) |
| O(3)—N(5) | 1.2194 (11) | N(3)—C(1) | 1.4562 (7) |
| O(4)—N(5) | 1.2218 (10) | N(3)—C(3) | 1.4692 (8) |
| O(5)—N(6) | 1.2212 (10) | C(1)—H(1A) | 1.065 (16) |
| O(6)—N(6) | 1.2248 (11) | C(1)—H(1B) | 1.072 (13) |
| N(1)—N(4) | 1.3558 (7) | C(2)—H(2A) | 1.043 (15) |
| N(1)—C(1) | 1.4645 (9) | C(2)—H(2B) | 1.088 (13) |
| N(1)—C(2) | 1.4663 (9) | C(3)—H(3A) | 1.080 (13) |
| N(2)—N(5) | 1.4046 (7) | C(3)—H(3B) | 1.090 (12) |
| N(2)—C(2) | 1.4553 (7) | ||
| N(4)—N(1)—C(1) | 119.50 (6) | N(1)—C(1)—N(3) | 107.93 (5) |
| N(4)—N(1)—C(2) | 120.23 (6) | N(1)—C(1)—H(1A) | 110.1 (6) |
| C(1)—N(1)—C(2) | 114.95 (5) | N(1)—C(1)—H(1B) | 109.0 (6) |
| N(5)—N(2)—C(2) | 115.71 (5) | N(3)—C(1)—H(1A) | 111.6 (6) |
| N(5)—N(2)—C(3) | 117.48 (6) | N(3)—C(1)—H(1B) | 106.7 (6) |
| C(2)—N(2)—C(3) | 114.93 (5) | H(1A)—C(1)—H(1B) | 111.4 (9) |
| N(6)—N(3)—C(1) | 115.80 (6) | N(1)—C(2)—N(2) | 107.78 (5) |
| N(6)—N(3)—C(3) | 116.32 (6) | N(1)—C(2)—H(2A) | 111.6 (6) |
| C(1)—N(3)—C(3) | 114.54 (6) | N(1)—C(2)—H(2B) | 108.6 (6) |
| O(1)—N(4)—O(2) | 125.01 (7) | N(2)—C(2)—H(2A) | 111.6 (6) |
| O(1)—N(4)—N(1) | 117.53 (7) | N(2)—C(2)—H(2B) | 106.5 (6) |
| O(2)—N(4)—N(1) | 117.42 (7) | H(2A)—C(2)—H(2B) | 110.6 (10) |
| O(3)—N(5)—O(4) | 125.79 (8) | N(2)—C(3)—N(3) | 112.36 (4) |
| O(3)—N(5)—N(2) | 116.87 (8) | N(2)—C(3)—H(3A) | 110.5 (6) |
| O(4)—N(5)—N(2) | 117.12 (7) | N(2)—C(3)—H(3B) | 107.1 (6) |
| O(5)—N(6)—O(6) | 125.67 (9) | N(3)—C(3)—H(3A) | 110.3 (6) |
| O(5)—N(6)—N(3) | 117.00 (8) | N(3)—C(3)—H(3B) | 105.9 (6) |
| O(6)—N(6)—N(3) | 117.12 (8) | H(3A)—C(3)—H(3B) | 110.6 (8) |
(RDX120KHarmonic) top
Crystal data top
| C3H6N6O6 | F(000) = 912.0 |
| Mr = 222.14 | Dx = 1.847 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 173199 reflections |
| a = 11.4425 (3) Å | θ = 3.0–66.8° |
| b = 10.6106 (3) Å | µ = 0.18 mm−1 |
| c = 13.1558 (4) Å | T = 120 K |
| V = 1597.27 (8) Å3 | Prism, colorless |
| Z = 8 | 0.29 × 0.29 × 0.17 mm |
Data collection top
| Rigaku R-axis Rapid diffractometer | Rint = 0.016 |
| w scans | θmax = 66.8° |
| 173199 measured reflections | h = −29→29 |
| 12304 independent reflections | k = −21→22 |
| 7986 reflections with I > 3σ, non−overlapped & non−partial reflections | l = −32→33 |
Refinement top
| Refinement on F2 | All H-atom parameters refined |
| R[F2 > 2σ(F2)] = 0.018 | w2 = q/[s2(Fo2) + (0.012 P)2 + 0.015 P + 0.00 + 0.00 sin(th)]
where P = (1.0000 Fo2 + 0.0000 Fc2) q = 1.0 |
| wR(F2) = 0.017 | (Δ/σ)max < 0.001 |
| S = 0.86 | Δρmax = 0.18 e Å−3 |
| 7986 reflections | Δρmin = −0.18 e Å−3 |
| 604 parameters |
Crystal data top
| C3H6N6O6 | V = 1597.27 (8) Å3 |
| Mr = 222.14 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα radiation |
| a = 11.4425 (3) Å | µ = 0.18 mm−1 |
| b = 10.6106 (3) Å | T = 120 K |
| c = 13.1558 (4) Å | 0.29 × 0.29 × 0.17 mm |
Data collection top
| Rigaku R-axis Rapid diffractometer | 7986 reflections with I > 3σ, non−overlapped & non−partial reflections |
| 173199 measured reflections | Rint = 0.016 |
| 12304 independent reflections |
Refinement top
| R[F2 > 2σ(F2)] = 0.018 | 604 parameters |
| wR(F2) = 0.017 | All H-atom parameters refined |
| S = 0.86 | Δρmax = 0.18 e Å−3 |
| 7986 reflections | Δρmin = −0.18 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O(1) | 0.56776 (3) | 0.43438 (4) | 0.26705 (2) | 0.016 | |
| O(2) | 0.59318 (3) | 0.23695 (5) | 0.22958 (3) | 0.020 | |
| O(3) | 0.46546 (4) | 0.13417 (5) | −0.02654 (4) | 0.022 | |
| O(4) | 0.35161 (4) | 0.25375 (5) | −0.11633 (2) | 0.020 | |
| O(5) | 0.31902 (4) | 0.53295 (5) | −0.07162 (3) | 0.020 | |
| O(6) | 0.43275 (3) | 0.60386 (4) | 0.04703 (4) | 0.021 | |
| N(1) | 0.434890 (17) | 0.33561 (2) | 0.174610 (16) | 0.012 | |
| N(2) | 0.318466 (16) | 0.23520 (2) | 0.050912 (14) | 0.011 | |
| N(3) | 0.296879 (17) | 0.45934 (2) | 0.086403 (15) | 0.011 | |
| N(4) | 0.536899 (14) | 0.33530 (2) | 0.227432 (13) | 0.012 | |
| N(5) | 0.384533 (16) | 0.20812 (2) | −0.036548 (14) | 0.013 | |
| N(6) | 0.355132 (16) | 0.534949 (19) | 0.014980 (16) | 0.014 | |
| C(1) | 0.355888 (17) | 0.44346 (2) | 0.183682 (15) | 0.013 | |
| C(2) | 0.378155 (18) | 0.21654 (2) | 0.147363 (14) | 0.012 | |
| C(3) | 0.240724 (15) | 0.34487 (2) | 0.047309 (14) | 0.011 | |
| H(1A) | 0.4048 (13) | 0.5269 (15) | 0.2046 (11) | 0.025 | |
| H(1B) | 0.2901 (13) | 0.4223 (13) | 0.2383 (10) | 0.026 | |
| H(2A) | 0.4392 (14) | 0.1425 (13) | 0.1435 (11) | 0.025 | |
| H(2B) | 0.3109 (13) | 0.1959 (14) | 0.2035 (11) | 0.027 | |
| H(3A) | 0.2094 (12) | 0.3601 (14) | −0.0291 (11) | 0.020 | |
| H(3B) | 0.1678 (12) | 0.3253 (12) | 0.0991 (10) | 0.020 |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O(1) | 0.01423 (8) | 0.02071 (13) | 0.01442 (9) | −0.00405 (9) | −0.00425 (7) | −0.00119 (9) |
| O(2) | 0.01457 (9) | 0.02009 (15) | 0.02402 (13) | 0.00268 (10) | −0.00619 (9) | 0.00376 (12) |
| O(3) | 0.01957 (11) | 0.02228 (16) | 0.02339 (15) | 0.00559 (11) | 0.00731 (10) | −0.00288 (13) |
| O(4) | 0.02403 (13) | 0.02673 (16) | 0.00925 (8) | −0.00094 (12) | 0.00329 (8) | −0.00143 (10) |
| O(5) | 0.02479 (13) | 0.02047 (15) | 0.01509 (10) | 0.00288 (12) | 0.00466 (9) | 0.00570 (11) |
| O(6) | 0.01672 (10) | 0.01540 (14) | 0.02986 (16) | −0.00389 (9) | 0.00620 (11) | 0.00031 (13) |
| N(1) | 0.01126 (5) | 0.01134 (8) | 0.01318 (6) | −0.00015 (5) | −0.00399 (5) | −0.00043 (6) |
| N(2) | 0.01044 (5) | 0.01249 (8) | 0.00890 (5) | −0.00101 (5) | 0.00023 (4) | −0.00121 (5) |
| N(3) | 0.00990 (5) | 0.01208 (8) | 0.01184 (6) | 0.00020 (5) | −0.00063 (4) | 0.00122 (6) |
| N(4) | 0.01027 (5) | 0.01587 (8) | 0.01044 (5) | −0.00122 (5) | −0.00227 (4) | 0.00218 (5) |
| N(5) | 0.01341 (5) | 0.01476 (7) | 0.01152 (5) | −0.00197 (5) | 0.00339 (4) | −0.00279 (5) |
| N(6) | 0.01248 (5) | 0.01183 (7) | 0.01679 (7) | 0.00193 (5) | 0.00428 (5) | 0.00268 (5) |
| C(1) | 0.01304 (6) | 0.01257 (8) | 0.01231 (6) | 0.00056 (5) | −0.00203 (5) | −0.00225 (6) |
| C(2) | 0.01466 (6) | 0.01080 (8) | 0.01096 (6) | −0.00141 (5) | −0.00178 (5) | 0.00122 (5) |
| C(3) | 0.00825 (5) | 0.01490 (8) | 0.01089 (6) | −0.00065 (5) | −0.00048 (4) | −0.00028 (5) |
| H(1A) | 0.028 (4) | 0.017 (4) | 0.029 (4) | 0.002 (3) | −0.006 (3) | −0.002 (3) |
| H(1B) | 0.024 (4) | 0.032 (4) | 0.022 (4) | 0.006 (3) | −0.001 (3) | −0.002 (3) |
| H(2A) | 0.026 (4) | 0.020 (4) | 0.031 (4) | 0.002 (3) | −0.009 (3) | −0.006 (3) |
| H(2B) | 0.027 (4) | 0.033 (4) | 0.022 (4) | −0.015 (3) | 0.007 (3) | −0.002 (3) |
| H(3A) | 0.018 (3) | 0.027 (4) | 0.015 (4) | 0.000 (3) | −0.003 (3) | 0.002 (3) |
| H(3B) | 0.016 (3) | 0.025 (3) | 0.021 (4) | −0.004 (3) | 0.005 (3) | 0.002 (3) |
Geometric parameters (Å, º) top
| O(1)—N(4) | 1.2255 (4) | N(2)—C(3) | 1.4655 (3) |
| O(2)—N(4) | 1.2265 (5) | N(3)—N(6) | 1.4038 (3) |
| O(3)—N(5) | 1.2208 (5) | N(3)—C(1) | 1.4568 (3) |
| O(4)—N(5) | 1.2157 (5) | N(3)—C(3) | 1.4672 (3) |
| O(5)—N(6) | 1.2122 (5) | C(1)—H(1A) | 1.083 (16) |
| O(6)—N(6) | 1.2253 (5) | C(1)—H(1B) | 1.064 (16) |
| N(1)—N(4) | 1.3584 (2) | C(2)—H(2A) | 1.052 (16) |
| N(1)—C(1) | 1.4632 (3) | C(2)—H(2B) | 1.089 (15) |
| N(1)—C(2) | 1.4650 (3) | C(3)—H(3A) | 1.079 (14) |
| N(2)—N(5) | 1.4064 (3) | C(3)—H(3B) | 1.096 (14) |
| N(2)—C(2) | 1.4546 (3) | ||
| N(4)—N(1)—C(1) | 119.41 (2) | N(1)—C(1)—N(3) | 107.769 (17) |
| N(4)—N(1)—C(2) | 120.25 (2) | N(1)—C(1)—H(1A) | 109.9 (7) |
| C(1)—N(1)—C(2) | 114.877 (17) | N(1)—C(1)—H(1B) | 109.1 (7) |
| N(5)—N(2)—C(2) | 115.688 (18) | N(3)—C(1)—H(1A) | 111.6 (8) |
| N(5)—N(2)—C(3) | 117.521 (19) | N(3)—C(1)—H(1B) | 106.8 (7) |
| C(2)—N(2)—C(3) | 114.919 (17) | H(1A)—C(1)—H(1B) | 111.5 (10) |
| N(6)—N(3)—C(1) | 115.725 (19) | N(1)—C(2)—N(2) | 107.705 (17) |
| N(6)—N(3)—C(3) | 116.512 (19) | N(1)—C(2)—H(2A) | 111.2 (7) |
| C(1)—N(3)—C(3) | 114.529 (19) | N(1)—C(2)—H(2B) | 108.7 (7) |
| O(1)—N(4)—O(2) | 124.67 (3) | N(2)—C(2)—H(2A) | 111.8 (7) |
| O(1)—N(4)—N(1) | 117.58 (3) | N(2)—C(2)—H(2B) | 106.7 (7) |
| O(2)—N(4)—N(1) | 117.71 (3) | H(2A)—C(2)—H(2B) | 110.6 (11) |
| O(3)—N(5)—O(4) | 125.74 (3) | N(2)—C(3)—N(3) | 112.345 (16) |
| O(3)—N(5)—N(2) | 116.79 (3) | N(2)—C(3)—H(3A) | 110.5 (7) |
| O(4)—N(5)—N(2) | 117.28 (3) | N(2)—C(3)—H(3B) | 107.0 (7) |
| O(5)—N(6)—O(6) | 125.52 (4) | N(3)—C(3)—H(3A) | 110.4 (8) |
| O(5)—N(6)—N(3) | 117.21 (3) | N(3)—C(3)—H(3B) | 105.8 (7) |
| O(6)—N(6)—N(3) | 117.06 (3) | H(3A)—C(3)—H(3B) | 110.7 (10) |
(RDX298KAnharmonic) top
Crystal data top
| C3H6N6O6 | F(000) = 912.0 |
| Mr = 222.14 | Dx = 1.794 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 238374 reflections |
| a = 11.6103 (4) Å | θ = 3.0–41.4° |
| b = 10.7291 (3) Å | µ = 0.17 mm−1 |
| c = 13.2013 (4) Å | T = 298 K |
| V = 1644.46 (8) Å3 | Pyramid, colorless |
| Z = 8 | 0.29 × 0.29 × 0.29 mm |
Data collection top
| Rigaku R-axis Rapid diffractometer | Rint = 0.017 |
| w scans | θmax = 41.4° |
| 238374 measured reflections | h = −21→21 |
| 5403 independent reflections | k = −19→19 |
| 3943 reflections with I > 3σ, non−overlapped & non−partial reflections | l = −24→24 |
Refinement top
| Refinement on F2 | All H-atom parameters refined |
| R[F2 > 2σ(F2)] = 0.010 | w2 = q/[s2(Fo2) + (0.005 P)2 + 0.006 P + 0.00 + 0.00 sin(th)]
where P = (1.0000 Fo2 + 0.0000 Fc2) q = 1.0 |
| wR(F2) = 0.008 | (Δ/σ)max < 0.001 |
| S = 1.25 | Δρmax = 0.06 e Å−3 |
| 3943 reflections | Δρmin = −0.05 e Å−3 |
| 859 parameters |
Crystal data top
| C3H6N6O6 | V = 1644.46 (8) Å3 |
| Mr = 222.14 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα radiation |
| a = 11.6103 (4) Å | µ = 0.17 mm−1 |
| b = 10.7291 (3) Å | T = 298 K |
| c = 13.2013 (4) Å | 0.29 × 0.29 × 0.29 mm |
Data collection top
| Rigaku R-axis Rapid diffractometer | 3943 reflections with I > 3σ, non−overlapped & non−partial reflections |
| 238374 measured reflections | Rint = 0.017 |
| 5403 independent reflections |
Refinement top
| R[F2 > 2σ(F2)] = 0.010 | 859 parameters |
| wR(F2) = 0.008 | All H-atom parameters refined |
| S = 1.25 | Δρmax = 0.06 e Å−3 |
| 3943 reflections | Δρmin = −0.05 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O(1) | 0.56849 (5) | 0.43256 (9) | 0.26366 (6) | 0.049 | |
| O(2) | 0.59335 (7) | 0.23759 (9) | 0.22690 (8) | 0.057 | |
| O(3) | 0.46859 (9) | 0.13864 (11) | −0.02406 (5) | 0.066 | |
| O(4) | 0.35312 (9) | 0.25231 (11) | −0.11236 (6) | 0.063 | |
| O(5) | 0.31348 (10) | 0.52470 (10) | −0.06986 (7) | 0.067 | |
| O(6) | 0.42704 (8) | 0.59865 (9) | 0.04471 (7) | 0.068 | |
| N(1) | 0.43602 (4) | 0.33305 (5) | 0.17611 (4) | 0.036 | |
| N(2) | 0.32173 (10) | 0.23215 (9) | 0.05365 (4) | 0.031 | |
| N(3) | 0.29937 (6) | 0.45302 (6) | 0.08758 (5) | 0.034 | |
| N(4) | 0.53767 (8) | 0.33450 (6) | 0.22577 (5) | 0.035 | |
| N(5) | 0.38757 (7) | 0.20834 (8) | −0.03336 (7) | 0.040 | |
| N(6) | 0.35216 (7) | 0.52895 (9) | 0.01551 (7) | 0.044 | |
| C(1) | 0.35879 (8) | 0.43948 (9) | 0.18356 (7) | 0.037 | |
| C(2) | 0.38160 (8) | 0.21563 (9) | 0.14918 (6) | 0.035 | |
| C(3) | 0.24457 (6) | 0.33925 (9) | 0.05052 (5) | 0.033 | |
| H(1A) | 0.4017 (11) | 0.5228 (12) | 0.2055 (9) | 0.062 | |
| H(1B) | 0.2921 (10) | 0.4197 (10) | 0.2394 (7) | 0.050 | |
| H(2A) | 0.4430 (12) | 0.1422 (9) | 0.1468 (9) | 0.056 | |
| H(2B) | 0.3156 (11) | 0.1931 (9) | 0.2066 (7) | 0.054 | |
| H(3A) | 0.2099 (8) | 0.3526 (9) | −0.0252 (8) | 0.051 | |
| H(3B) | 0.1736 (7) | 0.3198 (8) | 0.1017 (8) | 0.045 |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O(1) | 0.0421 (3) | 0.0628 (4) | 0.0419 (4) | −0.0161 (4) | −0.0126 (3) | −0.0013 (3) |
| O(2) | 0.0413 (3) | 0.0627 (4) | 0.0682 (4) | 0.0069 (4) | −0.0159 (4) | 0.0124 (5) |
| O(3) | 0.0583 (6) | 0.0619 (7) | 0.0771 (7) | 0.0126 (5) | 0.0252 (3) | −0.0122 (2) |
| O(4) | 0.0790 (5) | 0.0821 (5) | 0.0275 (3) | −0.0062 (5) | 0.0117 (4) | −0.0070 (4) |
| O(5) | 0.0887 (5) | 0.0653 (4) | 0.0481 (4) | 0.0178 (5) | 0.0189 (4) | 0.0249 (4) |
| O(6) | 0.0541 (6) | 0.0409 (5) | 0.1079 (7) | −0.0078 (4) | 0.0294 (3) | 0.0082 (5) |
| N(1) | 0.03502 (16) | 0.03163 (18) | 0.0406 (2) | −0.00053 (19) | −0.0129 (3) | −0.00134 (17) |
| N(2) | 0.0282 (4) | 0.0397 (3) | 0.0261 (3) | −0.0054 (4) | 0.0011 (4) | −0.0042 (3) |
| N(3) | 0.0295 (2) | 0.03497 (17) | 0.0365 (2) | 0.0007 (3) | 0.0005 (3) | 0.0048 (3) |
| N(4) | 0.0308 (4) | 0.0462 (5) | 0.0293 (3) | −0.0038 (2) | −0.0061 (3) | 0.0072 (2) |
| N(5) | 0.0411 (3) | 0.0442 (4) | 0.0356 (3) | −0.0079 (4) | 0.0109 (4) | −0.0095 (3) |
| N(6) | 0.0399 (3) | 0.0357 (4) | 0.0556 (3) | 0.0090 (3) | 0.0177 (4) | 0.0118 (4) |
| C(1) | 0.0397 (4) | 0.0333 (4) | 0.0389 (4) | 0.0015 (4) | −0.0053 (4) | −0.0062 (3) |
| C(2) | 0.0422 (4) | 0.0297 (4) | 0.0327 (4) | −0.0052 (4) | −0.0049 (3) | 0.0042 (3) |
| C(3) | 0.0219 (3) | 0.0477 (5) | 0.0292 (3) | −0.0029 (3) | −0.0006 (2) | −0.0008 (3) |
| H(1A) | 0.051 (4) | 0.051 (5) | 0.084 (5) | 0.001 (4) | −0.023 (3) | −0.010 (4) |
| H(1B) | 0.048 (4) | 0.067 (4) | 0.036 (3) | 0.008 (3) | −0.000 (3) | −0.008 (3) |
| H(2A) | 0.061 (5) | 0.042 (4) | 0.064 (4) | 0.001 (3) | −0.018 (4) | −0.001 (3) |
| H(2B) | 0.065 (5) | 0.051 (3) | 0.046 (4) | −0.019 (3) | −0.004 (3) | 0.006 (3) |
| H(3A) | 0.048 (3) | 0.065 (3) | 0.040 (4) | 0.003 (3) | −0.004 (3) | 0.003 (3) |
| H(3B) | 0.038 (4) | 0.048 (3) | 0.051 (4) | −0.009 (3) | 0.007 (3) | −0.000 (2) |
Geometric parameters (Å, º) top
| O(1)—N(4) | 1.2186 (13) | N(2)—C(3) | 1.4576 (12) |
| O(2)—N(4) | 1.2244 (13) | N(3)—N(6) | 1.3945 (15) |
| O(3)—N(5) | 1.2079 (12) | N(3)—C(1) | 1.4500 (11) |
| O(4)—N(5) | 1.2125 (14) | N(3)—C(3) | 1.4609 (12) |
| O(5)—N(6) | 1.2140 (14) | C(1)—H(1A) | 1.063 (14) |
| O(6)—N(6) | 1.2098 (13) | C(1)—H(1B) | 1.090 (12) |
| N(1)—N(4) | 1.3502 (13) | C(2)—H(2A) | 1.063 (13) |
| N(1)—C(1) | 1.4553 (12) | C(2)—H(2B) | 1.105 (12) |
| N(1)—C(2) | 1.4535 (12) | C(3)—H(3A) | 1.087 (10) |
| N(2)—N(5) | 1.4032 (13) | C(3)—H(3B) | 1.085 (10) |
| N(2)—C(2) | 1.4509 (12) | ||
| N(4)—N(1)—C(1) | 119.78 (6) | N(1)—C(1)—N(3) | 108.23 (8) |
| N(4)—N(1)—C(2) | 120.58 (6) | N(1)—C(1)—H(1A) | 112.9 (6) |
| C(1)—N(1)—C(2) | 115.39 (7) | N(1)—C(1)—H(1B) | 109.3 (6) |
| N(5)—N(2)—C(2) | 115.36 (8) | N(3)—C(1)—H(1A) | 112.1 (6) |
| N(5)—N(2)—C(3) | 117.07 (6) | N(3)—C(1)—H(1B) | 105.8 (5) |
| C(2)—N(2)—C(3) | 114.54 (7) | H(1A)—C(1)—H(1B) | 108.2 (9) |
| N(6)—N(3)—C(1) | 116.46 (6) | N(1)—C(2)—N(2) | 108.36 (8) |
| N(6)—N(3)—C(3) | 116.81 (7) | N(1)—C(2)—H(2A) | 111.0 (6) |
| C(1)—N(3)—C(3) | 114.59 (6) | N(1)—C(2)—H(2B) | 108.9 (5) |
| O(1)—N(4)—O(2) | 124.97 (8) | N(2)—C(2)—H(2A) | 112.7 (6) |
| O(1)—N(4)—N(1) | 117.77 (6) | N(2)—C(2)—H(2B) | 106.9 (5) |
| O(2)—N(4)—N(1) | 117.23 (7) | H(2A)—C(2)—H(2B) | 108.8 (8) |
| O(3)—N(5)—O(4) | 125.82 (8) | N(2)—C(3)—N(3) | 112.44 (8) |
| O(3)—N(5)—N(2) | 116.99 (7) | N(2)—C(3)—H(3A) | 110.9 (5) |
| O(4)—N(5)—N(2) | 116.97 (7) | N(2)—C(3)—H(3B) | 107.3 (5) |
| O(5)—N(6)—O(6) | 125.80 (9) | N(3)—C(3)—H(3A) | 111.1 (5) |
| O(5)—N(6)—N(3) | 116.67 (7) | N(3)—C(3)—H(3B) | 106.4 (5) |
| O(6)—N(6)—N(3) | 117.35 (7) | H(3A)—C(3)—H(3B) | 108.4 (7) |
(RDX298KHarmonic) top
Crystal data top
| C3H6N6O6 | F(000) = 912.0 |
| Mr = 222.14 | Dx = 1.794 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 238374 reflections |
| a = 11.6103 (4) Å | θ = 3.0–41.4° |
| b = 10.7291 (3) Å | µ = 0.17 mm−1 |
| c = 13.2013 (4) Å | T = 298 K |
| V = 1644.46 (8) Å3 | Pyramid, colorless |
| Z = 8 | 0.29 × 0.29 × 0.29 mm |
Data collection top
| Rigaku R-axis Rapid diffractometer | Rint = 0.017 |
| w scans | θmax = 41.4° |
| 238374 measured reflections | h = −21→21 |
| 5403 independent reflections | k = −19→19 |
| 3943 reflections with I > 3σ, non−overlapped & non−partial reflections | l = −24→24 |
Refinement top
| Refinement on F2 | All H-atom parameters refined |
| R[F2 > 2σ(F2)] = 0.018 | w2 = q/[s2(Fo2) + (0.015 P)2 + 0.056 P + 0.00 + 0.00 sin(th)]
where P = (1.0000 Fo2 + 0.0000 Fc2) q = 1.0 |
| wR(F2) = 0.020 | (Δ/σ)max < 0.001 |
| S = 1.14 | Δρmax = 0.15 e Å−3 |
| 3943 reflections | Δρmin = −0.11 e Å−3 |
| 604 parameters |
Crystal data top
| C3H6N6O6 | V = 1644.46 (8) Å3 |
| Mr = 222.14 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα radiation |
| a = 11.6103 (4) Å | µ = 0.17 mm−1 |
| b = 10.7291 (3) Å | T = 298 K |
| c = 13.2013 (4) Å | 0.29 × 0.29 × 0.29 mm |
Data collection top
| Rigaku R-axis Rapid diffractometer | 3943 reflections with I > 3σ, non−overlapped & non−partial reflections |
| 238374 measured reflections | Rint = 0.017 |
| 5403 independent reflections |
Refinement top
| R[F2 > 2σ(F2)] = 0.018 | 604 parameters |
| wR(F2) = 0.020 | All H-atom parameters refined |
| S = 1.14 | Δρmax = 0.15 e Å−3 |
| 3943 reflections | Δρmin = −0.11 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O(1) | 0.56846 (13) | 0.43427 (18) | 0.26465 (11) | 0.047 | |
| O(2) | 0.59453 (15) | 0.2404 (2) | 0.23053 (19) | 0.056 | |
| O(3) | 0.4734 (2) | 0.1388 (2) | −0.0225 (2) | 0.063 | |
| O(4) | 0.3558 (2) | 0.2495 (3) | −0.11238 (10) | 0.060 | |
| O(5) | 0.3181 (3) | 0.5303 (3) | −0.06806 (17) | 0.067 | |
| O(6) | 0.4286 (2) | 0.6011 (2) | 0.0492 (3) | 0.065 | |
| N(1) | 0.43638 (6) | 0.33385 (7) | 0.17584 (5) | 0.035 | |
| N(2) | 0.32231 (5) | 0.23197 (6) | 0.05389 (4) | 0.030 | |
| N(3) | 0.29900 (5) | 0.45348 (7) | 0.08838 (5) | 0.033 | |
| N(4) | 0.53777 (3) | 0.33516 (4) | 0.22628 (3) | 0.035 | |
| N(5) | 0.38834 (4) | 0.20759 (4) | −0.03308 (3) | 0.039 | |
| N(6) | 0.35299 (4) | 0.52971 (4) | 0.01650 (4) | 0.043 | |
| C(1) | 0.35799 (4) | 0.43950 (5) | 0.18450 (4) | 0.037 | |
| C(2) | 0.38140 (4) | 0.21557 (4) | 0.14950 (3) | 0.034 | |
| C(3) | 0.24458 (3) | 0.33936 (5) | 0.05038 (3) | 0.032 | |
| H(1A) | 0.402891 | 0.524029 | 0.207732 | 0.065 | |
| H(1B) | 0.290711 | 0.420236 | 0.239911 | 0.061 | |
| H(2A) | 0.443314 | 0.139185 | 0.1495 | 0.058 | |
| H(2B) | 0.317421 | 0.193899 | 0.207304 | 0.063 | |
| H(3A) | 0.209356 | 0.353637 | −0.025273 | 0.057 | |
| H(3B) | 0.172134 | 0.320912 | 0.1007 | 0.049 |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O(1) | 0.0408 (5) | 0.0593 (6) | 0.0408 (5) | −0.0119 (5) | −0.0113 (4) | −0.0009 (5) |
| O(2) | 0.0423 (6) | 0.0564 (9) | 0.0689 (8) | 0.0073 (6) | −0.0204 (6) | 0.0066 (8) |
| O(3) | 0.0568 (8) | 0.0612 (10) | 0.0714 (10) | 0.0101 (8) | 0.0229 (8) | −0.0085 (9) |
| O(4) | 0.0726 (10) | 0.0821 (10) | 0.0264 (4) | −0.0031 (10) | 0.0094 (5) | −0.0055 (5) |
| O(5) | 0.0911 (12) | 0.0640 (10) | 0.0471 (7) | 0.0182 (10) | 0.0220 (8) | 0.0221 (7) |
| O(6) | 0.0523 (8) | 0.0417 (7) | 0.1001 (11) | −0.0062 (6) | 0.0263 (8) | 0.0076 (9) |
| N(1) | 0.0339 (2) | 0.0319 (3) | 0.0383 (2) | −0.0010 (2) | −0.0127 (2) | −0.0010 (2) |
| N(2) | 0.0289 (2) | 0.0371 (3) | 0.02528 (18) | −0.00503 (19) | 0.00113 (17) | −0.00411 (19) |
| N(3) | 0.0273 (2) | 0.0353 (3) | 0.0359 (2) | 0.0015 (2) | 0.00031 (19) | 0.0057 (2) |
| N(4) | 0.02999 (15) | 0.0465 (2) | 0.02858 (14) | −0.00488 (15) | −0.00636 (12) | 0.00632 (15) |
| N(5) | 0.04057 (19) | 0.0432 (2) | 0.03390 (18) | −0.00748 (18) | 0.01102 (15) | −0.00976 (15) |
| N(6) | 0.0399 (2) | 0.0346 (2) | 0.0559 (3) | 0.00943 (19) | 0.01869 (19) | 0.01223 (19) |
| C(1) | 0.0377 (2) | 0.0347 (2) | 0.0376 (2) | 0.00117 (18) | −0.00672 (17) | −0.00722 (18) |
| C(2) | 0.0421 (2) | 0.0295 (2) | 0.03100 (18) | −0.00463 (17) | −0.00540 (16) | 0.00395 (15) |
| C(3) | 0.02192 (15) | 0.0459 (2) | 0.02935 (16) | −0.00240 (15) | −0.00089 (12) | −0.00013 (17) |
| H(1A) | 0.056 (8) | 0.030 (6) | 0.109 (12) | −0.010 (6) | 0.009 (8) | −0.014 (7) |
| H(1B) | 0.069 (8) | 0.075 (7) | 0.040 (5) | 0.009 (6) | 0.013 (5) | −0.009 (5) |
| H(2A) | 0.051 (7) | 0.048 (8) | 0.076 (8) | 0.004 (6) | −0.014 (6) | −0.009 (7) |
| H(2B) | 0.070 (8) | 0.066 (7) | 0.053 (7) | −0.037 (6) | 0.007 (6) | 0.016 (6) |
| H(3A) | 0.053 (7) | 0.077 (8) | 0.041 (6) | 0.011 (6) | 0.002 (6) | 0.004 (6) |
| H(3B) | 0.039 (6) | 0.056 (6) | 0.054 (7) | 0.000 (5) | 0.009 (5) | −0.006 (5) |
Geometric parameters (Å, º) top
| O(1)—N(4) | 1.2306 (16) | N(2)—C(3) | 1.4643 (8) |
| O(2)—N(4) | 1.213 (2) | N(3)—N(6) | 1.4008 (7) |
| O(3)—N(5) | 1.241 (3) | N(3)—C(1) | 1.4497 (8) |
| O(4)—N(5) | 1.200 (2) | N(3)—C(3) | 1.4663 (8) |
| O(5)—N(6) | 1.188 (3) | C(1)—H(1A) | 1.0900 |
| O(6)—N(6) | 1.242 (3) | C(1)—H(1B) | 1.0900 |
| N(1)—N(4) | 1.3525 (7) | C(2)—H(2A) | 1.0900 |
| N(1)—C(1) | 1.4582 (8) | C(2)—H(2B) | 1.0900 |
| N(1)—C(2) | 1.4625 (8) | C(3)—H(3A) | 1.0900 |
| N(2)—N(5) | 1.4051 (7) | C(3)—H(3B) | 1.0900 |
| N(2)—C(2) | 1.4474 (7) | ||
| N(4)—N(1)—C(1) | 119.77 (6) | N(1)—C(1)—N(3) | 107.86 (5) |
| N(4)—N(1)—C(2) | 120.40 (6) | N(1)—C(1)—H(1A) | 111.73 |
| C(1)—N(1)—C(2) | 114.88 (5) | N(1)—C(1)—H(1B) | 110.64 |
| N(5)—N(2)—C(2) | 115.55 (6) | N(3)—C(1)—H(1A) | 112.71 |
| N(5)—N(2)—C(3) | 117.19 (5) | N(3)—C(1)—H(1B) | 105.57 |
| C(2)—N(2)—C(3) | 114.54 (5) | H(1A)—C(1)—H(1B) | 108.16 |
| N(6)—N(3)—C(1) | 116.22 (6) | N(1)—C(2)—N(2) | 107.98 (4) |
| N(6)—N(3)—C(3) | 116.65 (6) | N(1)—C(2)—H(2A) | 111.38 |
| C(1)—N(3)—C(3) | 114.62 (5) | N(1)—C(2)—H(2B) | 108.43 |
| O(1)—N(4)—O(2) | 123.21 (14) | N(2)—C(2)—H(2A) | 113.82 |
| O(1)—N(4)—N(1) | 117.63 (9) | N(2)—C(2)—H(2B) | 108.27 |
| O(2)—N(4)—N(1) | 119.15 (12) | H(2A)—C(2)—H(2B) | 106.80 |
| O(3)—N(5)—O(4) | 124.84 (18) | N(2)—C(3)—N(3) | 112.38 (4) |
| O(3)—N(5)—N(2) | 116.95 (14) | N(2)—C(3)—H(3A) | 111.77 |
| O(4)—N(5)—N(2) | 118.12 (13) | N(2)—C(3)—H(3B) | 108.27 |
| O(5)—N(6)—O(6) | 124.3 (2) | N(3)—C(3)—H(3A) | 110.96 |
| O(5)—N(6)—N(3) | 119.16 (19) | N(3)—C(3)—H(3B) | 106.00 |
| O(6)—N(6)—N(3) | 116.18 (17) | H(3A)—C(3)—H(3B) | 107.12 |
Experimental details
| (RDX20KAnharmonic) | (RDX20KHarmonic) | (RDX120KAnharmonic) | (RDX120KHarmonic) | |
| Crystal data | ||||
| Chemical formula | C3H6N6O6 | C3H6N6O6 | C3H6N6O6 | C3H6N6O6 |
| Mr | 222.14 | 222.14 | 222.14 | 222.14 |
| Crystal system, space group | Orthorhombic, Pbca | Orthorhombic, Pbca | Orthorhombic, Pbca | Orthorhombic, Pbca |
| Temperature (K) | 20 | 20 | 120 | 120 |
| a, b, c (Å) | 11.3790 (2), 10.5694 (2), 13.1314 (2) | 11.3790 (2), 10.5694 (2), 13.1314 (2) | 11.4425 (3), 10.6106 (3), 13.1558 (4) | 11.4425 (3), 10.6106 (3), 13.1558 (4) |
| V (Å3) | 1579.30 (5) | 1579.30 (5) | 1597.27 (8) | 1597.27 (8) |
| Z | 8 | 8 | 8 | 8 |
| Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
| µ (mm−1) | 0.18 | 0.18 | 0.18 | 0.18 |
| Crystal size (mm) | 0.23 × 0.23 × 0.23 | 0.23 × 0.23 × 0.23 | 0.29 × 0.29 × 0.17 | 0.29 × 0.29 × 0.17 |
| Data collection | ||||
| Diffractometer | Rigaku R-axis Rapid diffractometer | Rigaku R-axis Rapid diffractometer | Rigaku R-axis Rapid diffractometer | Rigaku R-axis Rapid diffractometer |
| Absorption correction | – | – | – | – |
| No. of measured, independent and observed (I > 3σ, non−overlapped & non−partial reflections) reflections | 120142, 10651, 8057 | 120142, 10651, 8057 | 173199, 12304, 7986 | 173199, 12304, 7986 |
| Rint | 0.019 | 0.019 | 0.016 | 0.016 |
| (sin θ/λ)max (Å−1) | 1.322 | 1.322 | 1.293 | 1.293 |
| Refinement | ||||
| R[F2 > 2σ(F2)], wR(F2), S | 0.015, 0.010, 0.90 | 0.015, 0.011, 0.86 | 0.017, 0.013, 0.85 | 0.018, 0.017, 0.86 |
| No. of reflections | 8057 | 8057 | 7986 | 7986 |
| No. of parameters | 754 | 604 | 754 | 604 |
| No. of restraints | ? | ? | ? | ? |
| H-atom treatment | All H-atom parameters refined | All H-atom parameters refined | All H-atom parameters refined | All H-atom parameters refined |
| Δρmax, Δρmin (e Å−3) | 0.19, −0.17 | 0.19, −0.20 | 0.14, −0.15 | 0.18, −0.18 |
| (RDX298KAnharmonic) | (RDX298KHarmonic) | |
| Crystal data | ||
| Chemical formula | C3H6N6O6 | C3H6N6O6 |
| Mr | 222.14 | 222.14 |
| Crystal system, space group | Orthorhombic, Pbca | Orthorhombic, Pbca |
| Temperature (K) | 298 | 298 |
| a, b, c (Å) | 11.6103 (4), 10.7291 (3), 13.2013 (4) | 11.6103 (4), 10.7291 (3), 13.2013 (4) |
| V (Å3) | 1644.46 (8) | 1644.46 (8) |
| Z | 8 | 8 |
| Radiation type | Mo Kα | Mo Kα |
| µ (mm−1) | 0.17 | 0.17 |
| Crystal size (mm) | 0.29 × 0.29 × 0.29 | 0.29 × 0.29 × 0.29 |
| Data collection | ||
| Diffractometer | Rigaku R-axis Rapid diffractometer | Rigaku R-axis Rapid diffractometer |
| Absorption correction | – | – |
| No. of measured, independent and observed (I > 3σ, non−overlapped & non−partial reflections) reflections | 238374, 5403, 3943 | 238374, 5403, 3943 |
| Rint | 0.017 | 0.017 |
| (sin θ/λ)max (Å−1) | 0.931 | 0.931 |
| Refinement | ||
| R[F2 > 2σ(F2)], wR(F2), S | 0.010, 0.008, 1.25 | 0.018, 0.020, 1.14 |
| No. of reflections | 3943 | 3943 |
| No. of parameters | 859 | 604 |
| No. of restraints | ? | ? |
| H-atom treatment | All H-atom parameters refined | All H-atom parameters refined |
| Δρmax, Δρmin (e Å−3) | 0.06, −0.05 | 0.15, −0.11 |
Computer programs: CrystalClear,(2005), Otwinowski & Minor (1997), Zhurov et al.,(2005), Sheldrick (1997), Volkov et al., (2006).
Selected geometric parameters (Å, º) for (RDX20KAnharmonic) top
| O(1)—N(4) | 1.2288 (7) | N(2)—C(3) | 1.4654 (7) |
| O(2)—N(4) | 1.2347 (8) | N(3)—N(6) | 1.4027 (6) |
| O(3)—N(5) | 1.2220 (6) | N(3)—C(1) | 1.4570 (5) |
| O(4)—N(5) | 1.2234 (5) | N(3)—C(3) | 1.4681 (7) |
| O(5)—N(6) | 1.2220 (5) | C(1)—H(1A) | 1.070 (12) |
| O(6)—N(6) | 1.2270 (6) | C(1)—H(1B) | 1.085 (10) |
| N(1)—N(4) | 1.3592 (5) | C(2)—H(2A) | 1.059 (13) |
| N(1)—C(1) | 1.4634 (8) | C(2)—H(2B) | 1.089 (11) |
| N(1)—C(2) | 1.4661 (8) | C(3)—H(3A) | 1.058 (11) |
| N(2)—N(5) | 1.4063 (5) | C(3)—H(3B) | 1.079 (10) |
| N(2)—C(2) | 1.4555 (5) | ||
| N(4)—N(1)—C(1) | 119.33 (5) | N(1)—C(1)—N(3) | 107.68 (4) |
| N(4)—N(1)—C(2) | 120.09 (6) | N(1)—C(1)—H(1A) | 110.4 (5) |
| C(1)—N(1)—C(2) | 114.85 (4) | N(1)—C(1)—H(1B) | 109.8 (5) |
| N(5)—N(2)—C(2) | 115.73 (4) | N(3)—C(1)—H(1A) | 111.0 (5) |
| N(5)—N(2)—C(3) | 117.57 (4) | N(3)—C(1)—H(1B) | 106.5 (5) |
| C(2)—N(2)—C(3) | 115.07 (4) | H(1A)—C(1)—H(1B) | 111.3 (7) |
| N(6)—N(3)—C(1) | 115.70 (4) | N(1)—C(2)—N(2) | 107.58 (4) |
| N(6)—N(3)—C(3) | 116.34 (4) | N(1)—C(2)—H(2A) | 111.1 (5) |
| C(1)—N(3)—C(3) | 114.52 (5) | N(1)—C(2)—H(2B) | 109.3 (5) |
| O(1)—N(4)—O(2) | 124.95 (5) | N(2)—C(2)—H(2A) | 111.1 (5) |
| O(1)—N(4)—N(1) | 117.47 (6) | N(2)—C(2)—H(2B) | 107.2 (5) |
| O(2)—N(4)—N(1) | 117.53 (6) | H(2A)—C(2)—H(2B) | 110.5 (7) |
| O(3)—N(5)—O(4) | 125.94 (4) | N(2)—C(3)—N(3) | 112.29 (4) |
| O(3)—N(5)—N(2) | 116.77 (4) | N(2)—C(3)—H(3A) | 110.9 (5) |
| O(4)—N(5)—N(2) | 117.08 (5) | N(2)—C(3)—H(3B) | 106.1 (5) |
| O(5)—N(6)—O(6) | 125.50 (5) | N(3)—C(3)—H(3A) | 110.4 (5) |
| O(5)—N(6)—N(3) | 117.05 (5) | N(3)—C(3)—H(3B) | 106.4 (5) |
| O(6)—N(6)—N(3) | 117.24 (4) | H(3A)—C(3)—H(3B) | 110.7 (7) |
Selected geometric parameters (Å, º) for (RDX20KHarmonic) top
| O(1)—N(4) | 1.2263 (3) | N(2)—C(3) | 1.4658 (2) |
| O(2)—N(4) | 1.2312 (3) | N(3)—N(6) | 1.4038 (2) |
| O(3)—N(5) | 1.2189 (2) | N(3)—C(1) | 1.4565 (2) |
| O(4)—N(5) | 1.2203 (2) | N(3)—C(3) | 1.4673 (2) |
| O(5)—N(6) | 1.2180 (2) | C(1)—H(1A) | 1.069 (12) |
| O(6)—N(6) | 1.2233 (2) | C(1)—H(1B) | 1.089 (11) |
| N(1)—N(4) | 1.3586 (2) | C(2)—H(2A) | 1.056 (13) |
| N(1)—C(1) | 1.4624 (3) | C(2)—H(2B) | 1.088 (11) |
| N(1)—C(2) | 1.4654 (3) | C(3)—H(3A) | 1.056 (12) |
| N(2)—N(5) | 1.4059 (2) | C(3)—H(3B) | 1.077 (11) |
| N(2)—C(2) | 1.4549 (2) | ||
| N(4)—N(1)—C(1) | 119.379 (17) | N(1)—C(1)—N(3) | 107.759 (13) |
| N(4)—N(1)—C(2) | 120.105 (18) | N(1)—C(1)—H(1A) | 110.6 (6) |
| C(1)—N(1)—C(2) | 114.821 (14) | N(1)—C(1)—H(1B) | 109.8 (5) |
| N(5)—N(2)—C(2) | 115.799 (14) | N(3)—C(1)—H(1A) | 111.0 (6) |
| N(5)—N(2)—C(3) | 117.557 (14) | N(3)—C(1)—H(1B) | 106.6 (5) |
| C(2)—N(2)—C(3) | 115.016 (14) | H(1A)—C(1)—H(1B) | 111.0 (8) |
| N(6)—N(3)—C(1) | 115.680 (14) | N(1)—C(2)—N(2) | 107.623 (15) |
| N(6)—N(3)—C(3) | 116.370 (13) | N(1)—C(2)—H(2A) | 111.1 (6) |
| C(1)—N(3)—C(3) | 114.489 (16) | N(1)—C(2)—H(2B) | 109.2 (5) |
| O(1)—N(4)—O(2) | 124.850 (17) | N(2)—C(2)—H(2A) | 111.1 (6) |
| O(1)—N(4)—N(1) | 117.508 (18) | N(2)—C(2)—H(2B) | 107.4 (5) |
| O(2)—N(4)—N(1) | 117.599 (19) | H(2A)—C(2)—H(2B) | 110.3 (8) |
| O(3)—N(5)—O(4) | 125.886 (16) | N(2)—C(3)—N(3) | 112.337 (13) |
| O(3)—N(5)—N(2) | 116.763 (15) | N(2)—C(3)—H(3A) | 111.0 (6) |
| O(4)—N(5)—N(2) | 117.143 (16) | N(2)—C(3)—H(3B) | 106.0 (5) |
| O(5)—N(6)—O(6) | 125.632 (18) | N(3)—C(3)—H(3A) | 110.4 (6) |
| O(5)—N(6)—N(3) | 116.985 (17) | N(3)—C(3)—H(3B) | 106.5 (5) |
| O(6)—N(6)—N(3) | 117.176 (14) | H(3A)—C(3)—H(3B) | 110.4 (8) |
Selected geometric parameters (Å, º) for (RDX120KAnharmonic) top
| O(1)—N(4) | 1.2286 (10) | N(2)—C(3) | 1.4666 (8) |
| O(2)—N(4) | 1.2333 (11) | N(3)—N(6) | 1.4031 (8) |
| O(3)—N(5) | 1.2194 (11) | N(3)—C(1) | 1.4562 (7) |
| O(4)—N(5) | 1.2218 (10) | N(3)—C(3) | 1.4692 (8) |
| O(5)—N(6) | 1.2212 (10) | C(1)—H(1A) | 1.065 (16) |
| O(6)—N(6) | 1.2248 (11) | C(1)—H(1B) | 1.072 (13) |
| N(1)—N(4) | 1.3558 (7) | C(2)—H(2A) | 1.043 (15) |
| N(1)—C(1) | 1.4645 (9) | C(2)—H(2B) | 1.088 (13) |
| N(1)—C(2) | 1.4663 (9) | C(3)—H(3A) | 1.080 (13) |
| N(2)—N(5) | 1.4046 (7) | C(3)—H(3B) | 1.090 (12) |
| N(2)—C(2) | 1.4553 (7) | ||
| N(4)—N(1)—C(1) | 119.50 (6) | N(1)—C(1)—N(3) | 107.93 (5) |
| N(4)—N(1)—C(2) | 120.23 (6) | N(1)—C(1)—H(1A) | 110.1 (6) |
| C(1)—N(1)—C(2) | 114.95 (5) | N(1)—C(1)—H(1B) | 109.0 (6) |
| N(5)—N(2)—C(2) | 115.71 (5) | N(3)—C(1)—H(1A) | 111.6 (6) |
| N(5)—N(2)—C(3) | 117.48 (6) | N(3)—C(1)—H(1B) | 106.7 (6) |
| C(2)—N(2)—C(3) | 114.93 (5) | H(1A)—C(1)—H(1B) | 111.4 (9) |
| N(6)—N(3)—C(1) | 115.80 (6) | N(1)—C(2)—N(2) | 107.78 (5) |
| N(6)—N(3)—C(3) | 116.32 (6) | N(1)—C(2)—H(2A) | 111.6 (6) |
| C(1)—N(3)—C(3) | 114.54 (6) | N(1)—C(2)—H(2B) | 108.6 (6) |
| O(1)—N(4)—O(2) | 125.01 (7) | N(2)—C(2)—H(2A) | 111.6 (6) |
| O(1)—N(4)—N(1) | 117.53 (7) | N(2)—C(2)—H(2B) | 106.5 (6) |
| O(2)—N(4)—N(1) | 117.42 (7) | H(2A)—C(2)—H(2B) | 110.6 (10) |
| O(3)—N(5)—O(4) | 125.79 (8) | N(2)—C(3)—N(3) | 112.36 (4) |
| O(3)—N(5)—N(2) | 116.87 (8) | N(2)—C(3)—H(3A) | 110.5 (6) |
| O(4)—N(5)—N(2) | 117.12 (7) | N(2)—C(3)—H(3B) | 107.1 (6) |
| O(5)—N(6)—O(6) | 125.67 (9) | N(3)—C(3)—H(3A) | 110.3 (6) |
| O(5)—N(6)—N(3) | 117.00 (8) | N(3)—C(3)—H(3B) | 105.9 (6) |
| O(6)—N(6)—N(3) | 117.12 (8) | H(3A)—C(3)—H(3B) | 110.6 (8) |
Selected geometric parameters (Å, º) for (RDX120KHarmonic) top
| O(1)—N(4) | 1.2255 (4) | N(2)—C(3) | 1.4655 (3) |
| O(2)—N(4) | 1.2265 (5) | N(3)—N(6) | 1.4038 (3) |
| O(3)—N(5) | 1.2208 (5) | N(3)—C(1) | 1.4568 (3) |
| O(4)—N(5) | 1.2157 (5) | N(3)—C(3) | 1.4672 (3) |
| O(5)—N(6) | 1.2122 (5) | C(1)—H(1A) | 1.083 (16) |
| O(6)—N(6) | 1.2253 (5) | C(1)—H(1B) | 1.064 (16) |
| N(1)—N(4) | 1.3584 (2) | C(2)—H(2A) | 1.052 (16) |
| N(1)—C(1) | 1.4632 (3) | C(2)—H(2B) | 1.089 (15) |
| N(1)—C(2) | 1.4650 (3) | C(3)—H(3A) | 1.079 (14) |
| N(2)—N(5) | 1.4064 (3) | C(3)—H(3B) | 1.096 (14) |
| N(2)—C(2) | 1.4546 (3) | ||
| N(4)—N(1)—C(1) | 119.41 (2) | N(1)—C(1)—N(3) | 107.769 (17) |
| N(4)—N(1)—C(2) | 120.25 (2) | N(1)—C(1)—H(1A) | 109.9 (7) |
| C(1)—N(1)—C(2) | 114.877 (17) | N(1)—C(1)—H(1B) | 109.1 (7) |
| N(5)—N(2)—C(2) | 115.688 (18) | N(3)—C(1)—H(1A) | 111.6 (8) |
| N(5)—N(2)—C(3) | 117.521 (19) | N(3)—C(1)—H(1B) | 106.8 (7) |
| C(2)—N(2)—C(3) | 114.919 (17) | H(1A)—C(1)—H(1B) | 111.5 (10) |
| N(6)—N(3)—C(1) | 115.725 (19) | N(1)—C(2)—N(2) | 107.705 (17) |
| N(6)—N(3)—C(3) | 116.512 (19) | N(1)—C(2)—H(2A) | 111.2 (7) |
| C(1)—N(3)—C(3) | 114.529 (19) | N(1)—C(2)—H(2B) | 108.7 (7) |
| O(1)—N(4)—O(2) | 124.67 (3) | N(2)—C(2)—H(2A) | 111.8 (7) |
| O(1)—N(4)—N(1) | 117.58 (3) | N(2)—C(2)—H(2B) | 106.7 (7) |
| O(2)—N(4)—N(1) | 117.71 (3) | H(2A)—C(2)—H(2B) | 110.6 (11) |
| O(3)—N(5)—O(4) | 125.74 (3) | N(2)—C(3)—N(3) | 112.345 (16) |
| O(3)—N(5)—N(2) | 116.79 (3) | N(2)—C(3)—H(3A) | 110.5 (7) |
| O(4)—N(5)—N(2) | 117.28 (3) | N(2)—C(3)—H(3B) | 107.0 (7) |
| O(5)—N(6)—O(6) | 125.52 (4) | N(3)—C(3)—H(3A) | 110.4 (8) |
| O(5)—N(6)—N(3) | 117.21 (3) | N(3)—C(3)—H(3B) | 105.8 (7) |
| O(6)—N(6)—N(3) | 117.06 (3) | H(3A)—C(3)—H(3B) | 110.7 (10) |
Selected geometric parameters (Å, º) for (RDX298KAnharmonic) top
| O(1)—N(4) | 1.2186 (13) | N(2)—C(3) | 1.4576 (12) |
| O(2)—N(4) | 1.2244 (13) | N(3)—N(6) | 1.3945 (15) |
| O(3)—N(5) | 1.2079 (12) | N(3)—C(1) | 1.4500 (11) |
| O(4)—N(5) | 1.2125 (14) | N(3)—C(3) | 1.4609 (12) |
| O(5)—N(6) | 1.2140 (14) | C(1)—H(1A) | 1.063 (14) |
| O(6)—N(6) | 1.2098 (13) | C(1)—H(1B) | 1.090 (12) |
| N(1)—N(4) | 1.3502 (13) | C(2)—H(2A) | 1.063 (13) |
| N(1)—C(1) | 1.4553 (12) | C(2)—H(2B) | 1.105 (12) |
| N(1)—C(2) | 1.4535 (12) | C(3)—H(3A) | 1.087 (10) |
| N(2)—N(5) | 1.4032 (13) | C(3)—H(3B) | 1.085 (10) |
| N(2)—C(2) | 1.4509 (12) | ||
| N(4)—N(1)—C(1) | 119.78 (6) | N(1)—C(1)—N(3) | 108.23 (8) |
| N(4)—N(1)—C(2) | 120.58 (6) | N(1)—C(1)—H(1A) | 112.9 (6) |
| C(1)—N(1)—C(2) | 115.39 (7) | N(1)—C(1)—H(1B) | 109.3 (6) |
| N(5)—N(2)—C(2) | 115.36 (8) | N(3)—C(1)—H(1A) | 112.1 (6) |
| N(5)—N(2)—C(3) | 117.07 (6) | N(3)—C(1)—H(1B) | 105.8 (5) |
| C(2)—N(2)—C(3) | 114.54 (7) | H(1A)—C(1)—H(1B) | 108.2 (9) |
| N(6)—N(3)—C(1) | 116.46 (6) | N(1)—C(2)—N(2) | 108.36 (8) |
| N(6)—N(3)—C(3) | 116.81 (7) | N(1)—C(2)—H(2A) | 111.0 (6) |
| C(1)—N(3)—C(3) | 114.59 (6) | N(1)—C(2)—H(2B) | 108.9 (5) |
| O(1)—N(4)—O(2) | 124.97 (8) | N(2)—C(2)—H(2A) | 112.7 (6) |
| O(1)—N(4)—N(1) | 117.77 (6) | N(2)—C(2)—H(2B) | 106.9 (5) |
| O(2)—N(4)—N(1) | 117.23 (7) | H(2A)—C(2)—H(2B) | 108.8 (8) |
| O(3)—N(5)—O(4) | 125.82 (8) | N(2)—C(3)—N(3) | 112.44 (8) |
| O(3)—N(5)—N(2) | 116.99 (7) | N(2)—C(3)—H(3A) | 110.9 (5) |
| O(4)—N(5)—N(2) | 116.97 (7) | N(2)—C(3)—H(3B) | 107.3 (5) |
| O(5)—N(6)—O(6) | 125.80 (9) | N(3)—C(3)—H(3A) | 111.1 (5) |
| O(5)—N(6)—N(3) | 116.67 (7) | N(3)—C(3)—H(3B) | 106.4 (5) |
| O(6)—N(6)—N(3) | 117.35 (7) | H(3A)—C(3)—H(3B) | 108.4 (7) |
Selected geometric parameters (Å, º) for (RDX298KHarmonic) top
| O(1)—N(4) | 1.2306 (16) | N(2)—C(3) | 1.4643 (8) |
| O(2)—N(4) | 1.213 (2) | N(3)—N(6) | 1.4008 (7) |
| O(3)—N(5) | 1.241 (3) | N(3)—C(1) | 1.4497 (8) |
| O(4)—N(5) | 1.200 (2) | N(3)—C(3) | 1.4663 (8) |
| O(5)—N(6) | 1.188 (3) | C(1)—H(1A) | 1.0900 |
| O(6)—N(6) | 1.242 (3) | C(1)—H(1B) | 1.0900 |
| N(1)—N(4) | 1.3525 (7) | C(2)—H(2A) | 1.0900 |
| N(1)—C(1) | 1.4582 (8) | C(2)—H(2B) | 1.0900 |
| N(1)—C(2) | 1.4625 (8) | C(3)—H(3A) | 1.0900 |
| N(2)—N(5) | 1.4051 (7) | C(3)—H(3B) | 1.0900 |
| N(2)—C(2) | 1.4474 (7) | ||
| N(4)—N(1)—C(1) | 119.77 (6) | N(1)—C(1)—N(3) | 107.86 (5) |
| N(4)—N(1)—C(2) | 120.40 (6) | N(1)—C(1)—H(1A) | 111.73 |
| C(1)—N(1)—C(2) | 114.88 (5) | N(1)—C(1)—H(1B) | 110.64 |
| N(5)—N(2)—C(2) | 115.55 (6) | N(3)—C(1)—H(1A) | 112.71 |
| N(5)—N(2)—C(3) | 117.19 (5) | N(3)—C(1)—H(1B) | 105.57 |
| C(2)—N(2)—C(3) | 114.54 (5) | H(1A)—C(1)—H(1B) | 108.16 |
| N(6)—N(3)—C(1) | 116.22 (6) | N(1)—C(2)—N(2) | 107.98 (4) |
| N(6)—N(3)—C(3) | 116.65 (6) | N(1)—C(2)—H(2A) | 111.38 |
| C(1)—N(3)—C(3) | 114.62 (5) | N(1)—C(2)—H(2B) | 108.43 |
| O(1)—N(4)—O(2) | 123.21 (14) | N(2)—C(2)—H(2A) | 113.82 |
| O(1)—N(4)—N(1) | 117.63 (9) | N(2)—C(2)—H(2B) | 108.27 |
| O(2)—N(4)—N(1) | 119.15 (12) | H(2A)—C(2)—H(2B) | 106.80 |
| O(3)—N(5)—O(4) | 124.84 (18) | N(2)—C(3)—N(3) | 112.38 (4) |
| O(3)—N(5)—N(2) | 116.95 (14) | N(2)—C(3)—H(3A) | 111.77 |
| O(4)—N(5)—N(2) | 118.12 (13) | N(2)—C(3)—H(3B) | 108.27 |
| O(5)—N(6)—O(6) | 124.3 (2) | N(3)—C(3)—H(3A) | 110.96 |
| O(5)—N(6)—N(3) | 119.16 (19) | N(3)—C(3)—H(3B) | 106.00 |
| O(6)—N(6)—N(3) | 116.18 (17) | H(3A)—C(3)—H(3B) | 107.12 |
