Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768109006120/ry5024sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768109006120/ry50243asup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768109006120/ry50243bsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768109006120/ry50245sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768109006120/ry50245asup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768109006120/ry50245bsup6.hkl |
CCDC references: 654556; 654557; 654558; 654559; 654560
Data collection: DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998) for (3a), (5a). For all compounds, cell refinement: DENZO, COLLECT; data reduction: DENZO, COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: PLATON (Spek, 2003) for (3a), (5b); PLATON (Spek, 1990) for (3b), (5), (5a).
C18H24N5O2P3S2 | Dx = 1.496 Mg m−3 |
Mr = 499.45 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P41 | Cell parameters from 25190 reflections |
a = 11.4912 (1) Å | θ = 2.9–27.5° |
c = 16.7890 (2) Å | µ = 0.48 mm−1 |
V = 2216.95 (4) Å3 | T = 120 K |
Z = 4 | Prism, colourless |
F(000) = 1040 | 0.45 × 0.45 × 0.40 mm |
Bruker-Nonius KappaCCD Area Detector diffractometer | 5057 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 4976 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.5° |
φ and ω scans | h = −14→14 |
Absorption correction: multi-scan SADABS V2.10 (Sheldrick, G.M., 2003) | k = −14→14 |
Tmin = 0.812, Tmax = 0.830 | l = −21→21 |
41619 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.019 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.049 | w = 1/[σ2(Fo2) + (0.0283P)2 + 0.4819P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.028 |
5057 reflections | Δρmax = 0.16 e Å−3 |
279 parameters | Δρmin = −0.27 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (4) |
C18H24N5O2P3S2 | Z = 4 |
Mr = 499.45 | Mo Kα radiation |
Tetragonal, P41 | µ = 0.48 mm−1 |
a = 11.4912 (1) Å | T = 120 K |
c = 16.7890 (2) Å | 0.45 × 0.45 × 0.40 mm |
V = 2216.95 (4) Å3 |
Bruker-Nonius KappaCCD Area Detector diffractometer | 5057 independent reflections |
Absorption correction: multi-scan SADABS V2.10 (Sheldrick, G.M., 2003) | 4976 reflections with I > 2σ(I) |
Tmin = 0.812, Tmax = 0.830 | Rint = 0.031 |
41619 measured reflections |
R[F2 > 2σ(F2)] = 0.019 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.049 | Δρmax = 0.16 e Å−3 |
S = 1.04 | Δρmin = −0.27 e Å−3 |
5057 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
279 parameters | Absolute structure parameter: 0.01 (4) |
1 restraint |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.82968 (12) | 0.70919 (12) | −0.03729 (9) | 0.0140 (3) | |
C2 | 0.84909 (14) | 0.70813 (13) | −0.11901 (9) | 0.0213 (3) | |
H2 | 0.7906 | 0.6799 | −0.1540 | 0.026* | |
C3 | 0.95378 (15) | 0.74816 (14) | −0.14949 (11) | 0.0279 (4) | |
H3 | 0.9674 | 0.7470 | −0.2053 | 0.033* | |
C4 | 1.03848 (14) | 0.78984 (15) | −0.09813 (13) | 0.0323 (4) | |
H4 | 1.1100 | 0.8180 | −0.1190 | 0.039* | |
C5 | 1.01959 (14) | 0.79083 (14) | −0.01660 (12) | 0.0298 (4) | |
H5 | 1.0786 | 0.8186 | 0.0182 | 0.036* | |
C6 | 0.91472 (13) | 0.75134 (12) | 0.01447 (10) | 0.0204 (3) | |
H6 | 0.9011 | 0.7530 | 0.0703 | 0.024* | |
C7 | 0.83701 (13) | 0.29119 (12) | −0.05502 (8) | 0.0167 (3) | |
C8 | 0.95653 (13) | 0.29214 (13) | −0.06857 (9) | 0.0218 (3) | |
H8 | 0.9924 | 0.3590 | −0.0910 | 0.026* | |
C9 | 1.02309 (14) | 0.19564 (15) | −0.04931 (11) | 0.0270 (3) | |
H9 | 1.1047 | 0.1963 | −0.0584 | 0.032* | |
C10 | 0.97048 (16) | 0.09819 (14) | −0.01675 (10) | 0.0286 (4) | |
H10 | 1.0162 | 0.0321 | −0.0034 | 0.034* | |
C11 | 0.85125 (15) | 0.09674 (14) | −0.00354 (10) | 0.0274 (3) | |
H11 | 0.8157 | 0.0295 | 0.0187 | 0.033* | |
C12 | 0.78345 (14) | 0.19330 (14) | −0.02264 (9) | 0.0226 (3) | |
H12 | 0.7018 | 0.1924 | −0.0137 | 0.027* | |
C13 | 1.06017 (12) | 0.55367 (13) | 0.19484 (10) | 0.0198 (3) | |
H13A | 1.0897 | 0.6045 | 0.2379 | 0.024* | |
H13B | 1.0461 | 0.6026 | 0.1473 | 0.024* | |
C14 | 1.15054 (12) | 0.46183 (13) | 0.17538 (9) | 0.0195 (3) | |
H14A | 1.1703 | 0.4185 | 0.2245 | 0.023* | |
H14B | 1.2222 | 0.5005 | 0.1561 | 0.023* | |
C15 | 1.10837 (12) | 0.37624 (13) | 0.11235 (9) | 0.0179 (3) | |
H15A | 1.0932 | 0.4178 | 0.0617 | 0.021* | |
H15B | 1.1687 | 0.3165 | 0.1025 | 0.021* | |
C16 | 0.48367 (12) | 0.21635 (12) | 0.14389 (9) | 0.0162 (3) | |
H16A | 0.4673 | 0.1319 | 0.1401 | 0.019* | |
H16B | 0.4578 | 0.2534 | 0.0937 | 0.019* | |
C17 | 0.41647 (12) | 0.26789 (12) | 0.21348 (9) | 0.0164 (3) | |
H17A | 0.4364 | 0.2249 | 0.2627 | 0.020* | |
H17B | 0.3320 | 0.2584 | 0.2039 | 0.020* | |
C18 | 0.44380 (12) | 0.39665 (12) | 0.22502 (9) | 0.0163 (3) | |
H18A | 0.4192 | 0.4411 | 0.1774 | 0.020* | |
H18B | 0.4006 | 0.4270 | 0.2716 | 0.020* | |
N1 | 0.86791 (10) | 0.48911 (10) | 0.07770 (7) | 0.0130 (2) | |
N2 | 0.78575 (10) | 0.35315 (10) | 0.19822 (7) | 0.0135 (2) | |
N3 | 0.63816 (10) | 0.43377 (10) | 0.08397 (7) | 0.0144 (2) | |
N4 | 0.99934 (10) | 0.31974 (10) | 0.14119 (7) | 0.0143 (2) | |
N5 | 0.57020 (10) | 0.41122 (10) | 0.23778 (7) | 0.0133 (2) | |
O1 | 0.95170 (8) | 0.49992 (9) | 0.21982 (6) | 0.0155 (2) | |
O2 | 0.60888 (8) | 0.23459 (8) | 0.15424 (6) | 0.01375 (19) | |
P1 | 0.74443 (3) | 0.48918 (3) | 0.03601 (2) | 0.01101 (7) | |
P2 | 0.89259 (3) | 0.41507 (3) | 0.156756 (19) | 0.01033 (7) | |
P3 | 0.65592 (3) | 0.36334 (3) | 0.166283 (19) | 0.01027 (7) | |
S1 | 0.69478 (3) | 0.65851 (3) | 0.00226 (2) | 0.01505 (7) | |
S2 | 0.75390 (3) | 0.41789 (3) | −0.07875 (2) | 0.01936 (8) | |
H4N | 0.9798 (15) | 0.2640 (10) | 0.1107 (8) | 0.016 (4)* | |
H5N | 0.5911 (16) | 0.4761 (8) | 0.2574 (11) | 0.027 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0146 (6) | 0.0114 (6) | 0.0160 (6) | 0.0026 (5) | 0.0010 (5) | 0.0026 (5) |
C2 | 0.0246 (8) | 0.0206 (7) | 0.0188 (7) | 0.0014 (6) | 0.0034 (6) | 0.0022 (6) |
C3 | 0.0326 (9) | 0.0262 (8) | 0.0248 (8) | 0.0065 (7) | 0.0136 (7) | 0.0063 (7) |
C4 | 0.0184 (7) | 0.0234 (8) | 0.0552 (12) | 0.0043 (6) | 0.0110 (8) | 0.0163 (8) |
C5 | 0.0201 (8) | 0.0218 (8) | 0.0475 (11) | −0.0046 (6) | −0.0104 (7) | 0.0089 (7) |
C6 | 0.0236 (7) | 0.0163 (7) | 0.0213 (8) | 0.0004 (5) | −0.0045 (6) | 0.0023 (6) |
C7 | 0.0213 (7) | 0.0166 (7) | 0.0123 (6) | −0.0006 (5) | 0.0004 (5) | −0.0044 (5) |
C8 | 0.0230 (7) | 0.0202 (7) | 0.0222 (7) | −0.0042 (6) | 0.0049 (6) | −0.0068 (6) |
C9 | 0.0230 (8) | 0.0278 (9) | 0.0301 (9) | 0.0033 (7) | 0.0024 (7) | −0.0095 (7) |
C10 | 0.0388 (9) | 0.0190 (7) | 0.0280 (9) | 0.0076 (7) | −0.0048 (7) | −0.0062 (6) |
C11 | 0.0387 (9) | 0.0180 (7) | 0.0256 (8) | −0.0063 (7) | 0.0012 (7) | 0.0008 (6) |
C12 | 0.0239 (8) | 0.0227 (8) | 0.0212 (8) | −0.0047 (6) | 0.0039 (6) | −0.0036 (6) |
C13 | 0.0143 (7) | 0.0207 (7) | 0.0243 (8) | −0.0051 (5) | −0.0045 (6) | −0.0030 (6) |
C14 | 0.0107 (6) | 0.0236 (7) | 0.0241 (7) | −0.0020 (5) | −0.0046 (6) | 0.0033 (6) |
C15 | 0.0102 (6) | 0.0200 (7) | 0.0235 (8) | 0.0023 (5) | 0.0017 (5) | 0.0020 (6) |
C16 | 0.0145 (6) | 0.0147 (6) | 0.0193 (7) | −0.0038 (5) | −0.0046 (5) | −0.0006 (5) |
C17 | 0.0110 (6) | 0.0166 (6) | 0.0217 (7) | −0.0023 (5) | −0.0009 (5) | 0.0016 (5) |
C18 | 0.0094 (6) | 0.0168 (7) | 0.0226 (7) | 0.0009 (5) | 0.0004 (5) | −0.0017 (5) |
N1 | 0.0096 (5) | 0.0147 (5) | 0.0146 (6) | −0.0004 (4) | −0.0019 (4) | 0.0025 (4) |
N2 | 0.0102 (5) | 0.0174 (5) | 0.0128 (5) | 0.0007 (4) | −0.0016 (4) | 0.0029 (4) |
N3 | 0.0104 (5) | 0.0173 (6) | 0.0155 (6) | −0.0018 (4) | −0.0037 (4) | 0.0043 (4) |
N4 | 0.0113 (5) | 0.0126 (5) | 0.0189 (6) | 0.0008 (4) | −0.0003 (4) | 0.0003 (5) |
N5 | 0.0100 (5) | 0.0134 (5) | 0.0164 (6) | −0.0009 (4) | −0.0004 (4) | −0.0040 (4) |
O1 | 0.0127 (5) | 0.0189 (5) | 0.0150 (5) | −0.0020 (4) | −0.0034 (4) | −0.0043 (4) |
O2 | 0.0133 (4) | 0.0106 (4) | 0.0173 (5) | −0.0009 (3) | 0.0000 (4) | −0.0024 (4) |
P1 | 0.01067 (15) | 0.01207 (15) | 0.01030 (15) | 0.00029 (12) | −0.00227 (12) | 0.00081 (12) |
P2 | 0.00858 (14) | 0.01161 (15) | 0.01080 (15) | 0.00057 (11) | −0.00205 (12) | −0.00041 (12) |
P3 | 0.00929 (15) | 0.01051 (15) | 0.01102 (15) | −0.00029 (11) | −0.00140 (12) | −0.00001 (12) |
S1 | 0.01338 (15) | 0.01561 (16) | 0.01615 (16) | 0.00377 (12) | 0.00195 (13) | 0.00466 (12) |
S2 | 0.02553 (18) | 0.02081 (17) | 0.01174 (15) | 0.00217 (14) | −0.00373 (13) | −0.00313 (13) |
C1—C2 | 1.390 (2) | C15—N4 | 1.4919 (17) |
C1—C6 | 1.395 (2) | C16—O2 | 1.4643 (16) |
C1—S1 | 1.7841 (14) | C16—C17 | 1.521 (2) |
C2—C3 | 1.386 (2) | C17—C18 | 1.5249 (19) |
C3—C4 | 1.386 (3) | C18—N5 | 1.4777 (17) |
C4—C5 | 1.386 (3) | N1—P1 | 1.5821 (11) |
C5—C6 | 1.389 (2) | N1—P2 | 1.6019 (12) |
C7—C8 | 1.392 (2) | N2—P2 | 1.5805 (12) |
C7—C12 | 1.393 (2) | N2—P3 | 1.5896 (11) |
C7—S2 | 1.7861 (15) | N3—P1 | 1.5954 (12) |
C8—C9 | 1.385 (2) | N3—P3 | 1.6144 (12) |
C9—C10 | 1.385 (3) | N4—P2 | 1.6653 (12) |
C10—C11 | 1.388 (3) | N5—P3 | 1.6474 (12) |
C11—C12 | 1.393 (2) | O1—P2 | 1.5916 (10) |
C13—O1 | 1.4529 (17) | O2—P3 | 1.5881 (9) |
C13—C14 | 1.516 (2) | P1—S2 | 2.0964 (5) |
C14—C15 | 1.524 (2) | P1—S1 | 2.1054 (5) |
C2—C1—C6 | 120.37 (14) | C15—N4—P2 | 112.53 (9) |
C2—C1—S1 | 120.26 (12) | C18—N5—P3 | 116.37 (9) |
C6—C1—S1 | 119.36 (11) | C13—O1—P2 | 115.76 (9) |
C3—C2—C1 | 120.05 (16) | C16—O2—P3 | 118.88 (8) |
C2—C3—C4 | 119.65 (16) | N1—P1—N3 | 117.58 (6) |
C5—C4—C3 | 120.49 (16) | N1—P1—S2 | 111.09 (5) |
C4—C5—C6 | 120.27 (16) | N3—P1—S2 | 110.34 (5) |
C5—C6—C1 | 119.16 (15) | N1—P1—S1 | 111.25 (5) |
C8—C7—C12 | 120.40 (14) | N3—P1—S1 | 107.29 (5) |
C8—C7—S2 | 118.99 (11) | S2—P1—S1 | 97.35 (2) |
C12—C7—S2 | 120.61 (12) | N2—P2—O1 | 108.32 (6) |
C9—C8—C7 | 120.01 (14) | N2—P2—N1 | 117.81 (6) |
C8—C9—C10 | 119.89 (15) | O1—P2—N1 | 107.54 (6) |
C9—C10—C11 | 120.24 (16) | N2—P2—N4 | 110.19 (6) |
C10—C11—C12 | 120.37 (15) | O1—P2—N4 | 101.13 (6) |
C7—C12—C11 | 119.08 (15) | N1—P2—N4 | 110.47 (6) |
O1—C13—C14 | 110.73 (11) | O2—P3—N2 | 107.08 (6) |
C13—C14—C15 | 112.40 (11) | O2—P3—N3 | 108.37 (6) |
N4—C15—C14 | 108.82 (12) | N2—P3—N3 | 116.38 (6) |
O2—C16—C17 | 110.61 (11) | O2—P3—N5 | 101.56 (6) |
C16—C17—C18 | 111.77 (12) | N2—P3—N5 | 109.88 (6) |
N5—C18—C17 | 109.32 (11) | N3—P3—N5 | 112.38 (6) |
P1—N1—P2 | 121.71 (7) | C1—S1—P1 | 99.58 (5) |
P2—N2—P3 | 123.18 (7) | C7—S2—P1 | 98.12 (5) |
P1—N3—P3 | 122.37 (7) |
C18H24N5O2P3S2 | Dx = 1.497 Mg m−3 |
Mr = 499.45 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P43 | Cell parameters from 2618 reflections |
a = 11.4899 (1) Å | θ = 2.9–27.5° |
c = 16.7827 (2) Å | µ = 0.48 mm−1 |
V = 2215.62 (4) Å3 | T = 120 K |
Z = 4 | Block, colourless |
F(000) = 1040 | 0.55 × 0.20 × 0.20 mm |
Bruker-Nonius KappaCCD Area Detector diffractometer | 4532 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 4330 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.5° |
φ and ω scans | h = −12→14 |
Absorption correction: multi-scan SADABS V2.10 (Sheldrick, G.M., 2003) | k = −14→13 |
Tmin = 0.777, Tmax = 0.910 | l = −18→21 |
15809 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.066 | w = 1/[σ2(Fo2) + (0.0282P)2 + 0.916P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.004 |
4532 reflections | Δρmax = 0.19 e Å−3 |
279 parameters | Δρmin = −0.33 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.01 (5) |
C18H24N5O2P3S2 | Z = 4 |
Mr = 499.45 | Mo Kα radiation |
Tetragonal, P43 | µ = 0.48 mm−1 |
a = 11.4899 (1) Å | T = 120 K |
c = 16.7827 (2) Å | 0.55 × 0.20 × 0.20 mm |
V = 2215.62 (4) Å3 |
Bruker-Nonius KappaCCD Area Detector diffractometer | 4532 independent reflections |
Absorption correction: multi-scan SADABS V2.10 (Sheldrick, G.M., 2003) | 4330 reflections with I > 2σ(I) |
Tmin = 0.777, Tmax = 0.910 | Rint = 0.035 |
15809 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.066 | Δρmax = 0.19 e Å−3 |
S = 1.03 | Δρmin = −0.33 e Å−3 |
4532 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
279 parameters | Absolute structure parameter: −0.01 (5) |
1 restraint |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.67032 (19) | 1.20914 (19) | −0.15183 (13) | 0.0160 (4) | |
C2 | 0.5854 (2) | 1.2512 (2) | −0.10010 (14) | 0.0226 (5) | |
H2 | 0.5991 | 1.2530 | −0.0443 | 0.027* | |
C3 | 0.4801 (2) | 1.2906 (2) | −0.13141 (18) | 0.0316 (6) | |
H3 | 0.4209 | 1.3181 | −0.0966 | 0.038* | |
C4 | 0.4615 (2) | 1.2900 (2) | −0.21254 (19) | 0.0340 (6) | |
H4 | 0.3900 | 1.3182 | −0.2334 | 0.041* | |
C5 | 0.5461 (2) | 1.2485 (2) | −0.26394 (16) | 0.0293 (6) | |
H5 | 0.5325 | 1.2478 | −0.3198 | 0.035* | |
C6 | 0.6513 (2) | 1.2079 (2) | −0.23359 (14) | 0.0230 (5) | |
H6 | 0.7097 | 1.1794 | −0.2686 | 0.028* | |
C7 | 0.6630 (2) | 0.79102 (19) | −0.16944 (13) | 0.0186 (5) | |
C8 | 0.5436 (2) | 0.7924 (2) | −0.18311 (14) | 0.0236 (5) | |
H8 | 0.5077 | 0.8592 | −0.2056 | 0.028* | |
C9 | 0.4771 (2) | 0.6955 (2) | −0.16371 (16) | 0.0286 (6) | |
H9 | 0.3955 | 0.6960 | −0.1728 | 0.034* | |
C10 | 0.5298 (2) | 0.5983 (2) | −0.13104 (15) | 0.0306 (6) | |
H10 | 0.4843 | 0.5322 | −0.1174 | 0.037* | |
C11 | 0.6488 (2) | 0.5971 (2) | −0.11818 (15) | 0.0290 (6) | |
H11 | 0.6845 | 0.5297 | −0.0962 | 0.035* | |
C12 | 0.7164 (2) | 0.6932 (2) | −0.13702 (14) | 0.0244 (5) | |
H12 | 0.7980 | 0.6922 | −0.1279 | 0.029* | |
C13 | 1.01646 (19) | 0.71621 (19) | 0.02928 (13) | 0.0175 (4) | |
H13A | 1.0423 | 0.7532 | −0.0210 | 0.021* | |
H13B | 1.0328 | 0.6318 | 0.0256 | 0.021* | |
C14 | 1.08356 (19) | 0.76804 (19) | 0.09898 (14) | 0.0183 (5) | |
H14A | 1.0637 | 0.7250 | 0.1482 | 0.022* | |
H14B | 1.1681 | 0.7586 | 0.0894 | 0.022* | |
C15 | 1.05628 (18) | 0.8966 (2) | 0.11072 (14) | 0.0182 (4) | |
H15A | 1.0992 | 0.9267 | 0.1575 | 0.022* | |
H15B | 1.0812 | 0.9412 | 0.0632 | 0.022* | |
C16 | 0.43990 (19) | 1.0535 (2) | 0.08011 (14) | 0.0210 (5) | |
H16A | 0.4540 | 1.1021 | 0.0324 | 0.025* | |
H16B | 0.4104 | 1.1046 | 0.1231 | 0.025* | |
C17 | 0.34959 (18) | 0.9619 (2) | 0.06095 (14) | 0.0210 (5) | |
H17A | 0.2779 | 1.0005 | 0.0417 | 0.025* | |
H17B | 0.3299 | 0.9187 | 0.1102 | 0.025* | |
C18 | 0.39203 (19) | 0.8761 (2) | −0.00217 (14) | 0.0204 (5) | |
H18A | 0.3318 | 0.8163 | −0.0120 | 0.024* | |
H18B | 0.4072 | 0.9177 | −0.0528 | 0.024* | |
N1 | 0.86200 (15) | 0.93390 (16) | −0.03041 (11) | 0.0159 (4) | |
N2 | 0.71425 (15) | 0.85306 (16) | 0.08384 (11) | 0.0151 (4) | |
N3 | 0.63220 (15) | 0.98896 (16) | −0.03661 (10) | 0.0152 (4) | |
N4 | 0.92980 (15) | 0.91119 (16) | 0.12314 (11) | 0.0152 (4) | |
N5 | 0.50092 (15) | 0.81992 (16) | 0.02673 (11) | 0.0158 (4) | |
O1 | 0.89091 (12) | 0.73456 (12) | 0.03975 (9) | 0.0151 (3) | |
O2 | 0.54848 (13) | 0.99991 (13) | 0.10528 (9) | 0.0176 (3) | |
P1 | 0.75563 (5) | 0.98916 (5) | −0.07845 (3) | 0.01310 (11) | |
P2 | 0.84409 (4) | 0.86326 (5) | 0.05180 (3) | 0.01232 (11) | |
P3 | 0.60744 (4) | 0.91504 (5) | 0.04231 (3) | 0.01243 (11) | |
S1 | 0.80527 (5) | 1.15848 (5) | −0.11231 (3) | 0.01700 (12) | |
S2 | 0.74609 (5) | 0.91785 (5) | −0.19321 (3) | 0.02108 (12) | |
H4N | 0.908 (2) | 0.9754 (11) | 0.1431 (15) | 0.024 (7)* | |
H5N | 0.519 (2) | 0.7646 (15) | −0.0045 (12) | 0.022 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0174 (10) | 0.0141 (10) | 0.0165 (10) | −0.0032 (8) | 0.0004 (8) | 0.0034 (8) |
C2 | 0.0257 (12) | 0.0206 (11) | 0.0215 (12) | −0.0003 (9) | 0.0044 (9) | 0.0036 (9) |
C3 | 0.0219 (12) | 0.0248 (13) | 0.0483 (17) | 0.0041 (10) | 0.0102 (12) | 0.0073 (12) |
C4 | 0.0206 (12) | 0.0262 (13) | 0.0552 (18) | −0.0029 (10) | −0.0114 (12) | 0.0177 (13) |
C5 | 0.0336 (14) | 0.0283 (14) | 0.0259 (13) | −0.0071 (11) | −0.0141 (11) | 0.0059 (11) |
C6 | 0.0274 (13) | 0.0214 (12) | 0.0203 (11) | −0.0010 (10) | −0.0040 (10) | 0.0021 (9) |
C7 | 0.0229 (11) | 0.0187 (11) | 0.0143 (10) | 0.0011 (9) | −0.0010 (9) | −0.0052 (9) |
C8 | 0.0250 (12) | 0.0226 (12) | 0.0231 (12) | 0.0045 (9) | −0.0043 (10) | −0.0071 (10) |
C9 | 0.0245 (13) | 0.0321 (14) | 0.0293 (13) | −0.0037 (11) | −0.0028 (11) | −0.0111 (11) |
C10 | 0.0413 (15) | 0.0216 (12) | 0.0289 (13) | −0.0068 (11) | 0.0053 (12) | −0.0053 (10) |
C11 | 0.0406 (15) | 0.0203 (12) | 0.0262 (13) | 0.0048 (11) | −0.0009 (12) | 0.0021 (10) |
C12 | 0.0273 (13) | 0.0251 (13) | 0.0209 (12) | 0.0025 (10) | −0.0035 (10) | −0.0026 (10) |
C13 | 0.0173 (11) | 0.0173 (10) | 0.0179 (11) | 0.0047 (8) | 0.0032 (9) | 0.0001 (9) |
C14 | 0.0135 (10) | 0.0183 (11) | 0.0232 (12) | 0.0019 (9) | 0.0009 (9) | 0.0013 (9) |
C15 | 0.0112 (10) | 0.0204 (11) | 0.0228 (11) | −0.0017 (9) | 0.0001 (9) | −0.0018 (9) |
C16 | 0.0149 (11) | 0.0226 (11) | 0.0257 (12) | 0.0045 (9) | 0.0037 (9) | −0.0040 (10) |
C17 | 0.0122 (10) | 0.0264 (12) | 0.0243 (12) | 0.0016 (9) | 0.0046 (9) | 0.0040 (10) |
C18 | 0.0120 (10) | 0.0246 (12) | 0.0245 (12) | −0.0018 (9) | −0.0026 (9) | −0.0003 (10) |
N1 | 0.0124 (8) | 0.0190 (9) | 0.0164 (9) | 0.0020 (7) | 0.0032 (7) | 0.0039 (7) |
N2 | 0.0128 (9) | 0.0187 (9) | 0.0139 (8) | −0.0004 (7) | 0.0011 (7) | 0.0026 (7) |
N3 | 0.0131 (8) | 0.0172 (9) | 0.0153 (9) | 0.0002 (7) | 0.0014 (7) | 0.0032 (7) |
N4 | 0.0130 (9) | 0.0154 (9) | 0.0172 (9) | 0.0008 (7) | 0.0024 (7) | −0.0037 (7) |
N5 | 0.0128 (9) | 0.0154 (9) | 0.0190 (9) | −0.0013 (7) | 0.0011 (7) | 0.0002 (8) |
O1 | 0.0148 (7) | 0.0133 (7) | 0.0172 (7) | 0.0006 (6) | 0.0006 (6) | −0.0027 (6) |
O2 | 0.0152 (7) | 0.0209 (8) | 0.0166 (7) | 0.0021 (6) | 0.0036 (6) | −0.0036 (6) |
P1 | 0.0135 (3) | 0.0149 (3) | 0.0110 (2) | −0.0002 (2) | 0.0019 (2) | 0.0007 (2) |
P2 | 0.0118 (2) | 0.0129 (2) | 0.0123 (2) | 0.00023 (19) | 0.0014 (2) | 0.0003 (2) |
P3 | 0.0116 (2) | 0.0143 (3) | 0.0115 (2) | −0.0005 (2) | 0.0020 (2) | −0.0003 (2) |
S1 | 0.0158 (3) | 0.0182 (3) | 0.0169 (2) | −0.0036 (2) | −0.0020 (2) | 0.0044 (2) |
S2 | 0.0273 (3) | 0.0231 (3) | 0.0129 (2) | −0.0023 (2) | 0.0036 (2) | −0.0030 (2) |
C1—C6 | 1.390 (3) | C15—N4 | 1.478 (3) |
C1—C2 | 1.392 (3) | C16—O2 | 1.454 (3) |
C1—S1 | 1.784 (2) | C16—C17 | 1.512 (3) |
C2—C3 | 1.395 (4) | C17—C18 | 1.527 (3) |
C3—C4 | 1.378 (4) | C18—N5 | 1.489 (3) |
C4—C5 | 1.384 (4) | N1—P1 | 1.5959 (18) |
C5—C6 | 1.391 (4) | N1—P2 | 1.6140 (19) |
C7—C8 | 1.391 (3) | N2—P3 | 1.5809 (18) |
C7—C12 | 1.392 (3) | N2—P2 | 1.5901 (18) |
C7—S2 | 1.787 (2) | N3—P1 | 1.5825 (18) |
C8—C9 | 1.389 (4) | N3—P3 | 1.5989 (18) |
C9—C10 | 1.385 (4) | N4—P2 | 1.6451 (19) |
C10—C11 | 1.384 (4) | N5—P3 | 1.6615 (19) |
C11—C12 | 1.387 (4) | O1—P2 | 1.5865 (15) |
C13—O1 | 1.468 (2) | O2—P3 | 1.5896 (15) |
C13—C14 | 1.522 (3) | P1—S2 | 2.0959 (8) |
C14—C15 | 1.522 (3) | P1—S1 | 2.1055 (8) |
C6—C1—C2 | 120.6 (2) | C15—N4—P2 | 116.62 (14) |
C6—C1—S1 | 120.04 (18) | C18—N5—P3 | 112.63 (14) |
C2—C1—S1 | 119.36 (18) | C13—O1—P2 | 118.83 (13) |
C1—C2—C3 | 119.0 (2) | C16—O2—P3 | 115.61 (13) |
C4—C3—C2 | 120.3 (2) | N3—P1—N1 | 117.49 (10) |
C3—C4—C5 | 120.6 (2) | N3—P1—S2 | 111.12 (7) |
C4—C5—C6 | 119.8 (2) | N1—P1—S2 | 110.41 (7) |
C1—C6—C5 | 119.7 (2) | N3—P1—S1 | 111.34 (7) |
C8—C7—C12 | 120.6 (2) | N1—P1—S1 | 107.25 (7) |
C8—C7—S2 | 118.74 (18) | S2—P1—S1 | 97.31 (3) |
C12—C7—S2 | 120.69 (19) | O1—P2—N2 | 107.01 (9) |
C9—C8—C7 | 119.7 (2) | O1—P2—N1 | 108.45 (9) |
C10—C9—C8 | 119.9 (2) | N2—P2—N1 | 116.47 (9) |
C11—C10—C9 | 120.1 (2) | O1—P2—N4 | 101.64 (9) |
C10—C11—C12 | 120.7 (2) | N2—P2—N4 | 109.89 (9) |
C11—C12—C7 | 119.0 (2) | N1—P2—N4 | 112.17 (9) |
O1—C13—C14 | 110.45 (17) | N2—P3—O2 | 108.30 (9) |
C15—C14—C13 | 112.00 (18) | N2—P3—N3 | 117.80 (10) |
N4—C15—C14 | 109.33 (17) | O2—P3—N3 | 107.50 (9) |
O2—C16—C17 | 110.85 (18) | N2—P3—N5 | 110.18 (9) |
C16—C17—C18 | 112.17 (18) | O2—P3—N5 | 101.20 (9) |
N5—C18—C17 | 108.80 (18) | N3—P3—N5 | 110.49 (10) |
P1—N1—P2 | 122.29 (11) | C1—S1—P1 | 99.57 (7) |
P3—N2—P2 | 123.09 (11) | C7—S2—P1 | 98.14 (7) |
P1—N3—P3 | 121.86 (11) |
C18H24N5O4P3 | Dx = 1.495 Mg m−3 |
Mr = 467.33 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbcn | Cell parameters from 4837 reflections |
a = 38.7541 (16) Å | θ = 2.9–27.5° |
b = 10.1505 (4) Å | µ = 0.32 mm−1 |
c = 10.5550 (5) Å | T = 120 K |
V = 4152.1 (3) Å3 | Needle, colourless |
Z = 8 | 0.65 × 0.02 × 0.01 mm |
F(000) = 1952 |
Bruker APEX2 diffractometer | 4703 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 3961 reflections with I > 2σ(I) |
10cm confocal mirrors monochromator | Rint = 0.055 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.5° |
φ and ω scans | h = −50→50 |
Absorption correction: multi-scan SADABS V2.10 (Sheldrick, G.M., 2003) | k = −13→11 |
Tmin = 0.817, Tmax = 0.997 | l = −13→11 |
19961 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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.P)2 + 15.046P] where P = (Fo2 + 2Fc2)/3 |
4703 reflections | (Δ/σ)max < 0.001 |
279 parameters | Δρmax = 0.55 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
C18H24N5O4P3 | V = 4152.1 (3) Å3 |
Mr = 467.33 | Z = 8 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 38.7541 (16) Å | µ = 0.32 mm−1 |
b = 10.1505 (4) Å | T = 120 K |
c = 10.5550 (5) Å | 0.65 × 0.02 × 0.01 mm |
Bruker APEX2 diffractometer | 4703 independent reflections |
Absorption correction: multi-scan SADABS V2.10 (Sheldrick, G.M., 2003) | 3961 reflections with I > 2σ(I) |
Tmin = 0.817, Tmax = 0.997 | Rint = 0.055 |
19961 measured reflections |
R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.P)2 + 15.046P] where P = (Fo2 + 2Fc2)/3 |
4703 reflections | Δρmax = 0.55 e Å−3 |
279 parameters | Δρmin = −0.43 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.36017 (9) | 0.3751 (3) | 0.5506 (3) | 0.0302 (8) | |
H1A | 0.3613 | 0.3794 | 0.4570 | 0.036* | |
H1B | 0.3839 | 0.3826 | 0.5844 | 0.036* | |
C2 | 0.33821 (9) | 0.4871 (4) | 0.6006 (4) | 0.0327 (8) | |
H2A | 0.3489 | 0.5724 | 0.5773 | 0.039* | |
H2B | 0.3150 | 0.4832 | 0.5616 | 0.039* | |
C3 | 0.33495 (9) | 0.4781 (3) | 0.7433 (4) | 0.0326 (8) | |
H3A | 0.3582 | 0.4834 | 0.7822 | 0.039* | |
H3B | 0.3211 | 0.5532 | 0.7749 | 0.039* | |
C4 | 0.25752 (9) | −0.0680 (4) | 0.9491 (5) | 0.0467 (12) | |
H4A | 0.2441 | −0.0104 | 0.8916 | 0.056* | |
H4B | 0.2447 | −0.0750 | 1.0300 | 0.056* | |
C5 | 0.26078 (10) | −0.2034 (4) | 0.8906 (5) | 0.0519 (13) | |
H5A | 0.2729 | −0.2629 | 0.9501 | 0.062* | |
H5B | 0.2375 | −0.2399 | 0.8745 | 0.062* | |
C6 | 0.28041 (11) | −0.1963 (4) | 0.7688 (5) | 0.0502 (13) | |
H6A | 0.2812 | −0.2849 | 0.7296 | 0.060* | |
H6B | 0.2683 | −0.1364 | 0.7095 | 0.060* | |
C7 | 0.44017 (7) | −0.0336 (3) | 0.9473 (3) | 0.0209 (6) | |
C8 | 0.43182 (8) | −0.0875 (3) | 1.0632 (3) | 0.0237 (7) | |
H8 | 0.4116 | −0.0606 | 1.1070 | 0.028* | |
C9 | 0.45373 (9) | −0.1825 (3) | 1.1146 (3) | 0.0263 (7) | |
H9 | 0.4483 | −0.2212 | 1.1941 | 0.032* | |
C10 | 0.48323 (8) | −0.2209 (3) | 1.0513 (3) | 0.0276 (7) | |
H10 | 0.4981 | −0.2848 | 1.0877 | 0.033* | |
C11 | 0.49106 (8) | −0.1657 (3) | 0.9342 (3) | 0.0276 (7) | |
H11 | 0.5113 | −0.1923 | 0.8902 | 0.033* | |
C12 | 0.46941 (8) | −0.0723 (3) | 0.8818 (3) | 0.0238 (7) | |
H12 | 0.4746 | −0.0349 | 0.8014 | 0.029* | |
C13 | 0.40613 (7) | 0.2587 (3) | 1.1054 (3) | 0.0206 (6) | |
C14 | 0.40683 (8) | 0.2685 (3) | 1.2360 (3) | 0.0268 (7) | |
H14 | 0.3932 | 0.2117 | 1.2870 | 0.032* | |
C15 | 0.42782 (9) | 0.3629 (4) | 1.2911 (4) | 0.0328 (8) | |
H15 | 0.4285 | 0.3706 | 1.3808 | 0.039* | |
C16 | 0.44778 (9) | 0.4462 (4) | 1.2174 (4) | 0.0318 (8) | |
H16 | 0.4622 | 0.5104 | 1.2561 | 0.038* | |
C17 | 0.44651 (9) | 0.4350 (3) | 1.0862 (4) | 0.0292 (7) | |
H17 | 0.4601 | 0.4920 | 1.0352 | 0.035* | |
C18 | 0.42556 (8) | 0.3414 (3) | 1.0289 (3) | 0.0250 (7) | |
H18 | 0.4246 | 0.3342 | 0.9392 | 0.030* | |
N1 | 0.31327 (7) | 0.1027 (3) | 0.7586 (3) | 0.0245 (6) | |
N2 | 0.35745 (6) | −0.0157 (3) | 0.9234 (3) | 0.0222 (6) | |
N3 | 0.37388 (6) | 0.2199 (3) | 0.8187 (3) | 0.0218 (6) | |
N4 | 0.34500 (7) | 0.2495 (3) | 0.5898 (3) | 0.0228 (6) | |
N5 | 0.29128 (7) | −0.0080 (3) | 0.9732 (3) | 0.0309 (7) | |
O1 | 0.31856 (6) | 0.3554 (2) | 0.7800 (2) | 0.0251 (5) | |
O2 | 0.31564 (6) | −0.1487 (2) | 0.7892 (3) | 0.0332 (6) | |
O3 | 0.42063 (5) | 0.0639 (2) | 0.8864 (2) | 0.0225 (5) | |
O4 | 0.38410 (5) | 0.1615 (2) | 1.0584 (2) | 0.0222 (5) | |
P1 | 0.338309 (19) | 0.22429 (8) | 0.74061 (8) | 0.01890 (18) | |
P2 | 0.320197 (19) | −0.01163 (8) | 0.85954 (8) | 0.02149 (19) | |
P3 | 0.382158 (19) | 0.10819 (8) | 0.91629 (8) | 0.01875 (18) | |
H5N | 0.2998 (9) | −0.035 (3) | 1.0427 (18) | 0.026 (10)* | |
H4N | 0.3529 (10) | 0.185 (3) | 0.548 (4) | 0.046 (13)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0302 (17) | 0.0336 (19) | 0.0267 (18) | −0.0035 (14) | 0.0011 (14) | 0.0095 (15) |
C2 | 0.0302 (17) | 0.0254 (18) | 0.042 (2) | −0.0015 (14) | −0.0065 (16) | 0.0089 (16) |
C3 | 0.0325 (18) | 0.0205 (17) | 0.045 (2) | 0.0040 (14) | −0.0033 (16) | −0.0077 (16) |
C4 | 0.0157 (16) | 0.048 (2) | 0.076 (3) | −0.0015 (16) | −0.0007 (17) | 0.026 (2) |
C5 | 0.0249 (18) | 0.036 (2) | 0.095 (4) | −0.0091 (16) | −0.020 (2) | 0.026 (2) |
C6 | 0.050 (2) | 0.0242 (19) | 0.076 (3) | −0.0015 (17) | −0.041 (2) | 0.001 (2) |
C7 | 0.0168 (13) | 0.0218 (15) | 0.0243 (16) | −0.0015 (11) | −0.0019 (12) | −0.0010 (13) |
C8 | 0.0189 (14) | 0.0266 (16) | 0.0256 (17) | 0.0002 (12) | 0.0026 (12) | 0.0005 (14) |
C9 | 0.0298 (16) | 0.0267 (17) | 0.0225 (17) | −0.0016 (13) | −0.0002 (13) | 0.0032 (14) |
C10 | 0.0252 (16) | 0.0240 (17) | 0.0335 (19) | 0.0013 (13) | −0.0037 (14) | −0.0010 (14) |
C11 | 0.0203 (15) | 0.0304 (18) | 0.0321 (19) | 0.0014 (13) | 0.0033 (13) | −0.0014 (15) |
C12 | 0.0173 (14) | 0.0284 (17) | 0.0258 (17) | −0.0020 (12) | 0.0040 (12) | −0.0004 (14) |
C13 | 0.0160 (13) | 0.0206 (15) | 0.0250 (16) | 0.0041 (11) | −0.0012 (12) | −0.0008 (13) |
C14 | 0.0255 (16) | 0.0301 (18) | 0.0249 (17) | 0.0012 (13) | −0.0007 (13) | −0.0009 (14) |
C15 | 0.0341 (18) | 0.036 (2) | 0.0282 (18) | 0.0028 (15) | −0.0054 (15) | −0.0047 (16) |
C16 | 0.0294 (17) | 0.0278 (18) | 0.038 (2) | 0.0002 (14) | −0.0080 (15) | −0.0074 (16) |
C17 | 0.0257 (16) | 0.0263 (17) | 0.0356 (19) | 0.0000 (13) | −0.0027 (14) | 0.0036 (15) |
C18 | 0.0246 (15) | 0.0279 (17) | 0.0224 (16) | 0.0012 (13) | −0.0014 (13) | −0.0002 (14) |
N1 | 0.0195 (12) | 0.0249 (14) | 0.0291 (15) | −0.0024 (10) | −0.0058 (11) | 0.0062 (12) |
N2 | 0.0184 (12) | 0.0221 (13) | 0.0261 (14) | −0.0018 (10) | −0.0015 (11) | 0.0034 (11) |
N3 | 0.0183 (12) | 0.0239 (14) | 0.0233 (14) | −0.0013 (10) | −0.0035 (10) | 0.0043 (11) |
N4 | 0.0260 (13) | 0.0247 (14) | 0.0176 (13) | 0.0001 (11) | −0.0007 (11) | 0.0003 (12) |
N5 | 0.0186 (13) | 0.0371 (17) | 0.0369 (18) | 0.0016 (12) | −0.0025 (12) | 0.0130 (14) |
O1 | 0.0225 (11) | 0.0247 (12) | 0.0282 (12) | 0.0026 (9) | 0.0021 (9) | −0.0036 (10) |
O2 | 0.0367 (14) | 0.0238 (12) | 0.0391 (15) | −0.0013 (10) | −0.0123 (11) | −0.0028 (11) |
O3 | 0.0164 (10) | 0.0286 (12) | 0.0227 (11) | 0.0018 (9) | 0.0024 (8) | 0.0060 (10) |
O4 | 0.0205 (10) | 0.0257 (11) | 0.0206 (11) | −0.0036 (9) | −0.0001 (9) | −0.0003 (9) |
P1 | 0.0174 (4) | 0.0202 (4) | 0.0191 (4) | 0.0011 (3) | −0.0007 (3) | 0.0001 (3) |
P2 | 0.0174 (4) | 0.0205 (4) | 0.0266 (4) | −0.0015 (3) | −0.0029 (3) | 0.0025 (3) |
P3 | 0.0149 (3) | 0.0222 (4) | 0.0192 (4) | −0.0003 (3) | 0.0001 (3) | 0.0012 (3) |
C1—N4 | 1.463 (4) | C13—O4 | 1.395 (4) |
C1—C2 | 1.515 (5) | C14—C15 | 1.385 (5) |
C2—C3 | 1.514 (5) | C15—C16 | 1.385 (5) |
C3—O1 | 1.451 (4) | C16—C17 | 1.390 (5) |
C4—N5 | 1.465 (4) | C17—C18 | 1.388 (5) |
C4—C5 | 1.512 (7) | N1—P1 | 1.582 (3) |
C5—C6 | 1.496 (7) | N1—P2 | 1.598 (3) |
C6—O2 | 1.464 (4) | N2—P3 | 1.582 (3) |
C7—C8 | 1.378 (4) | N2—P2 | 1.594 (3) |
C7—C12 | 1.385 (4) | N3—P3 | 1.565 (3) |
C7—O3 | 1.402 (4) | N3—P1 | 1.606 (3) |
C8—C9 | 1.395 (5) | N4—P1 | 1.633 (3) |
C9—C10 | 1.380 (5) | N5—P2 | 1.642 (3) |
C10—C11 | 1.391 (5) | O1—P1 | 1.590 (2) |
C11—C12 | 1.382 (5) | O2—P2 | 1.587 (3) |
C13—C14 | 1.383 (5) | O3—P3 | 1.589 (2) |
C13—C18 | 1.387 (4) | O4—P3 | 1.597 (2) |
N4—C1—C2 | 109.3 (3) | C1—N4—P1 | 118.4 (2) |
C3—C2—C1 | 110.3 (3) | C4—N5—P2 | 118.2 (3) |
O1—C3—C2 | 110.7 (3) | C3—O1—P1 | 116.0 (2) |
N5—C4—C5 | 112.0 (3) | C6—O2—P2 | 117.5 (2) |
C6—C5—C4 | 110.5 (3) | C7—O3—P3 | 128.0 (2) |
O2—C6—C5 | 111.3 (3) | C13—O4—P3 | 127.0 (2) |
C8—C7—C12 | 121.5 (3) | N1—P1—O1 | 109.05 (14) |
C8—C7—O3 | 124.1 (3) | N1—P1—N3 | 116.29 (14) |
C12—C7—O3 | 114.4 (3) | O1—P1—N3 | 107.59 (14) |
C7—C8—C9 | 118.5 (3) | N1—P1—N4 | 109.70 (15) |
C10—C9—C8 | 120.7 (3) | O1—P1—N4 | 101.53 (14) |
C9—C10—C11 | 119.8 (3) | N3—P1—N4 | 111.59 (14) |
C12—C11—C10 | 120.0 (3) | O2—P2—N2 | 106.02 (14) |
C11—C12—C7 | 119.5 (3) | O2—P2—N1 | 107.81 (15) |
C14—C13—C18 | 121.7 (3) | N2—P2—N1 | 116.93 (14) |
C14—C13—O4 | 114.6 (3) | O2—P2—N5 | 106.60 (16) |
C18—C13—O4 | 123.6 (3) | N2—P2—N5 | 108.05 (15) |
C13—C14—C15 | 118.7 (3) | N1—P2—N5 | 110.86 (15) |
C14—C15—C16 | 120.9 (3) | N3—P3—N2 | 118.87 (14) |
C15—C16—C17 | 119.3 (3) | N3—P3—O3 | 105.48 (13) |
C18—C17—C16 | 120.7 (3) | N2—P3—O3 | 110.61 (13) |
C13—C18—C17 | 118.6 (3) | N3—P3—O4 | 112.51 (14) |
P1—N1—P2 | 122.95 (17) | N2—P3—O4 | 104.68 (13) |
P3—N2—P2 | 120.48 (17) | O3—P3—O4 | 103.77 (12) |
P3—N3—P1 | 122.26 (17) |
C18H24N5O4P3 | Dx = 1.465 Mg m−3 |
Mr = 467.33 | Mo Kα radiation, λ = 0.71073 Å |
Trigonal, P32 | Cell parameters from 2347 reflections |
a = 10.4920 (1) Å | θ = 2.9–27.5° |
c = 16.6645 (3) Å | µ = 0.32 mm−1 |
V = 1588.69 (4) Å3 | T = 120 K |
Z = 3 | Block, colourless |
F(000) = 732 | 0.50 × 0.40 × 0.34 mm |
Bruker-Nonius KappaCCD Area Detector diffractometer | 4848 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 4802 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.3° |
φ and ω scans | h = −13→13 |
Absorption correction: multi-scan SADABS V2.10 (Sheldrick, G.M., 2003) | k = −11→11 |
Tmin = 0.858, Tmax = 0.900 | l = −21→21 |
4871 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.072 | w = 1/[σ2(Fo2) + (0.0389P)2 + 0.8904P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.021 |
4848 reflections | Δρmax = 0.18 e Å−3 |
280 parameters | Δρmin = −0.38 e Å−3 |
3 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.06 (8) |
C18H24N5O4P3 | Z = 3 |
Mr = 467.33 | Mo Kα radiation |
Trigonal, P32 | µ = 0.32 mm−1 |
a = 10.4920 (1) Å | T = 120 K |
c = 16.6645 (3) Å | 0.50 × 0.40 × 0.34 mm |
V = 1588.69 (4) Å3 |
Bruker-Nonius KappaCCD Area Detector diffractometer | 4848 independent reflections |
Absorption correction: multi-scan SADABS V2.10 (Sheldrick, G.M., 2003) | 4802 reflections with I > 2σ(I) |
Tmin = 0.858, Tmax = 0.900 | Rint = 0.048 |
4871 measured reflections |
R[F2 > 2σ(F2)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.072 | Δρmax = 0.18 e Å−3 |
S = 1.02 | Δρmin = −0.38 e Å−3 |
4848 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
280 parameters | Absolute structure parameter: −0.06 (8) |
3 restraints |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.5989 (3) | 1.0664 (3) | 0.99501 (16) | 0.0175 (5) | |
C2 | 0.6981 (3) | 1.2019 (3) | 0.96413 (18) | 0.0249 (6) | |
H2 | 0.6980 | 1.2215 | 0.9085 | 0.030* | |
C3 | 0.7981 (4) | 1.3094 (4) | 1.0152 (2) | 0.0316 (7) | |
H3 | 0.8664 | 1.4039 | 0.9947 | 0.038* | |
C4 | 0.7987 (4) | 1.2796 (4) | 1.0961 (2) | 0.0315 (7) | |
H4 | 0.8672 | 1.3540 | 1.1310 | 0.038* | |
C5 | 0.7003 (4) | 1.1423 (4) | 1.12636 (18) | 0.0302 (7) | |
H5 | 0.7020 | 1.1220 | 1.1818 | 0.036* | |
C6 | 0.5991 (3) | 1.0343 (3) | 1.07577 (18) | 0.0251 (6) | |
H6 | 0.5309 | 0.9396 | 1.0961 | 0.030* | |
C7 | 0.3613 (3) | 0.6262 (3) | 0.81817 (16) | 0.0148 (5) | |
C8 | 0.3212 (3) | 0.4953 (3) | 0.85581 (17) | 0.0232 (6) | |
H8 | 0.3098 | 0.4869 | 0.9125 | 0.028* | |
C9 | 0.2974 (4) | 0.3749 (3) | 0.80942 (19) | 0.0277 (7) | |
H9 | 0.2696 | 0.2834 | 0.8346 | 0.033* | |
C10 | 0.3140 (3) | 0.3878 (3) | 0.72724 (18) | 0.0218 (6) | |
H10 | 0.2991 | 0.3058 | 0.6960 | 0.026* | |
C11 | 0.3523 (3) | 0.5202 (3) | 0.69040 (16) | 0.0235 (6) | |
H11 | 0.3621 | 0.5285 | 0.6337 | 0.028* | |
C12 | 0.3765 (3) | 0.6414 (3) | 0.73619 (16) | 0.0221 (6) | |
H12 | 0.4029 | 0.7328 | 0.7113 | 0.026* | |
C13 | 0.6087 (3) | 0.5161 (3) | 1.02805 (18) | 0.0235 (6) | |
H13A | 0.5877 | 0.4137 | 1.0209 | 0.028* | |
H13B | 0.5137 | 0.5148 | 1.0285 | 0.028* | |
C14 | 0.6869 (4) | 0.5755 (4) | 1.10715 (19) | 0.0261 (7) | |
H14A | 0.7762 | 0.5662 | 1.1087 | 0.031* | |
H14B | 0.6215 | 0.5154 | 1.1514 | 0.031* | |
C15 | 0.7306 (3) | 0.7351 (4) | 1.12042 (16) | 0.0231 (6) | |
H15A | 0.6414 | 0.7437 | 1.1264 | 0.028* | |
H15B | 0.7894 | 0.7718 | 1.1702 | 0.028* | |
N4 | 0.8183 (3) | 0.8242 (3) | 1.05117 (13) | 0.0173 (5) | |
C16 | 0.9219 (3) | 1.1999 (3) | 0.76421 (16) | 0.0200 (6) | |
H16A | 1.0010 | 1.3035 | 0.7705 | 0.024* | |
H16B | 0.8261 | 1.1966 | 0.7674 | 0.024* | |
C17 | 0.9363 (3) | 1.1422 (3) | 0.68278 (17) | 0.0221 (6) | |
H17A | 0.9231 | 1.2000 | 0.6400 | 0.027* | |
H17B | 1.0367 | 1.1568 | 0.6775 | 0.027* | |
C18 | 0.8257 (3) | 0.9813 (3) | 0.67088 (15) | 0.0207 (6) | |
H18A | 0.7250 | 0.9669 | 0.6698 | 0.025* | |
H18B | 0.8440 | 0.9474 | 0.6189 | 0.025* | |
N5 | 0.8383 (3) | 0.8942 (3) | 0.73720 (13) | 0.0160 (4) | |
N1 | 0.5814 (2) | 0.7685 (3) | 0.96406 (13) | 0.0139 (4) | |
N2 | 0.8474 (2) | 0.8609 (3) | 0.89470 (14) | 0.0147 (4) | |
N3 | 0.6528 (2) | 0.9339 (3) | 0.83125 (13) | 0.0151 (4) | |
O1 | 0.4938 (2) | 0.9583 (2) | 0.94427 (11) | 0.0155 (4) | |
O2 | 0.3803 (2) | 0.7472 (2) | 0.86408 (11) | 0.0151 (4) | |
O3 | 0.6979 (2) | 0.6057 (2) | 0.96134 (11) | 0.0178 (4) | |
O4 | 0.9321 (2) | 1.1113 (2) | 0.82846 (11) | 0.0165 (4) | |
P1 | 0.53976 (7) | 0.85171 (7) | 0.90071 (4) | 0.01200 (11) | |
P2 | 0.73541 (7) | 0.77205 (7) | 0.96437 (3) | 0.01212 (12) | |
P3 | 0.80971 (7) | 0.94302 (7) | 0.82731 (4) | 0.01249 (12) | |
H5N | 0.794 (4) | 0.8026 (13) | 0.732 (3) | 0.041 (12)* | |
H4N | 0.857 (4) | 0.9153 (14) | 1.060 (2) | 0.035 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0160 (12) | 0.0191 (13) | 0.0214 (12) | 0.0118 (11) | −0.0040 (10) | −0.0082 (10) |
C2 | 0.0271 (16) | 0.0191 (14) | 0.0267 (13) | 0.0103 (12) | −0.0050 (12) | −0.0018 (12) |
C3 | 0.0310 (17) | 0.0196 (14) | 0.0425 (18) | 0.0113 (13) | −0.0112 (14) | −0.0099 (13) |
C4 | 0.0319 (16) | 0.0321 (17) | 0.0393 (18) | 0.0225 (15) | −0.0182 (14) | −0.0193 (14) |
C5 | 0.0345 (18) | 0.0441 (19) | 0.0206 (13) | 0.0262 (15) | −0.0102 (12) | −0.0123 (13) |
C6 | 0.0265 (15) | 0.0297 (16) | 0.0225 (13) | 0.0166 (13) | −0.0038 (12) | −0.0050 (12) |
C7 | 0.0121 (12) | 0.0128 (12) | 0.0209 (12) | 0.0073 (10) | −0.0020 (10) | −0.0028 (10) |
C8 | 0.0298 (15) | 0.0167 (13) | 0.0224 (13) | 0.0112 (12) | 0.0060 (12) | 0.0038 (11) |
C9 | 0.0343 (17) | 0.0118 (12) | 0.0349 (16) | 0.0100 (12) | 0.0113 (13) | 0.0051 (11) |
C10 | 0.0164 (13) | 0.0167 (13) | 0.0308 (14) | 0.0071 (12) | −0.0041 (11) | −0.0072 (11) |
C11 | 0.0336 (16) | 0.0256 (15) | 0.0176 (12) | 0.0195 (13) | −0.0071 (11) | −0.0048 (11) |
C12 | 0.0311 (16) | 0.0210 (14) | 0.0188 (13) | 0.0165 (12) | −0.0045 (12) | 0.0001 (11) |
C13 | 0.0165 (13) | 0.0173 (13) | 0.0375 (16) | 0.0089 (11) | 0.0091 (12) | 0.0114 (12) |
C14 | 0.0265 (16) | 0.0315 (17) | 0.0252 (14) | 0.0181 (14) | 0.0115 (12) | 0.0177 (13) |
C15 | 0.0239 (15) | 0.0343 (17) | 0.0155 (12) | 0.0180 (13) | 0.0065 (11) | 0.0064 (11) |
N4 | 0.0177 (11) | 0.0195 (12) | 0.0144 (11) | 0.0092 (10) | 0.0002 (9) | 0.0010 (9) |
C16 | 0.0220 (14) | 0.0163 (13) | 0.0209 (13) | 0.0090 (11) | 0.0018 (11) | 0.0067 (11) |
C17 | 0.0218 (14) | 0.0267 (14) | 0.0198 (13) | 0.0135 (12) | 0.0069 (11) | 0.0093 (11) |
C18 | 0.0233 (14) | 0.0296 (16) | 0.0126 (11) | 0.0158 (13) | 0.0003 (10) | 0.0016 (10) |
N5 | 0.0186 (11) | 0.0160 (11) | 0.0133 (10) | 0.0087 (9) | 0.0009 (9) | −0.0004 (8) |
N1 | 0.0128 (10) | 0.0175 (11) | 0.0138 (10) | 0.0094 (9) | 0.0025 (8) | 0.0037 (8) |
N2 | 0.0145 (10) | 0.0175 (10) | 0.0139 (9) | 0.0093 (9) | 0.0010 (8) | 0.0022 (7) |
N3 | 0.0150 (10) | 0.0184 (11) | 0.0142 (9) | 0.0099 (9) | −0.0003 (8) | 0.0026 (8) |
O1 | 0.0149 (9) | 0.0165 (9) | 0.0185 (9) | 0.0103 (8) | −0.0031 (7) | −0.0044 (7) |
O2 | 0.0134 (8) | 0.0141 (9) | 0.0190 (8) | 0.0079 (7) | −0.0037 (7) | −0.0040 (7) |
O3 | 0.0198 (9) | 0.0148 (9) | 0.0216 (9) | 0.0108 (8) | 0.0038 (8) | 0.0028 (8) |
O4 | 0.0163 (9) | 0.0142 (9) | 0.0168 (9) | 0.0059 (8) | −0.0007 (7) | 0.0024 (7) |
P1 | 0.0109 (3) | 0.0124 (3) | 0.0134 (2) | 0.0064 (3) | 0.0003 (2) | 0.0003 (2) |
P2 | 0.0115 (3) | 0.0132 (3) | 0.0129 (3) | 0.0070 (3) | 0.0015 (2) | 0.0020 (2) |
P3 | 0.0121 (3) | 0.0129 (3) | 0.0116 (3) | 0.0056 (3) | 0.0008 (2) | 0.0010 (2) |
C1—C2 | 1.375 (4) | C15—N4 | 1.480 (3) |
C1—C6 | 1.388 (4) | N4—P2 | 1.635 (2) |
C1—O1 | 1.403 (3) | C16—O4 | 1.456 (3) |
C2—C3 | 1.383 (4) | C16—C17 | 1.524 (4) |
C3—C4 | 1.386 (5) | C17—C18 | 1.509 (4) |
C4—C5 | 1.381 (5) | C18—N5 | 1.482 (3) |
C5—C6 | 1.386 (4) | N5—P3 | 1.662 (2) |
C7—C8 | 1.370 (4) | N1—P1 | 1.565 (2) |
C7—C12 | 1.376 (4) | N1—P2 | 1.597 (2) |
C7—O2 | 1.408 (3) | N2—P3 | 1.582 (2) |
C8—C9 | 1.393 (4) | N2—P2 | 1.582 (2) |
C9—C10 | 1.379 (4) | N3—P1 | 1.571 (2) |
C10—C11 | 1.382 (4) | N3—P3 | 1.602 (2) |
C11—C12 | 1.393 (4) | O1—P1 | 1.5969 (19) |
C13—O3 | 1.455 (3) | O2—P1 | 1.5936 (18) |
C13—C14 | 1.512 (5) | O3—P2 | 1.5862 (19) |
C14—C15 | 1.514 (5) | O4—P3 | 1.5805 (19) |
C2—C1—C6 | 121.5 (3) | P3—N2—P2 | 121.82 (13) |
C2—C1—O1 | 119.6 (2) | P1—N3—P3 | 122.32 (14) |
C6—C1—O1 | 119.0 (3) | C1—O1—P1 | 116.74 (16) |
C1—C2—C3 | 119.1 (3) | C7—O2—P1 | 117.07 (16) |
C2—C3—C4 | 120.2 (3) | C13—O3—P2 | 114.37 (17) |
C5—C4—C3 | 120.3 (3) | C16—O4—P3 | 115.24 (16) |
C4—C5—C6 | 119.9 (3) | N1—P1—N3 | 117.27 (11) |
C5—C6—C1 | 119.0 (3) | N1—P1—O2 | 111.37 (12) |
C8—C7—C12 | 122.1 (3) | N3—P1—O2 | 109.89 (11) |
C8—C7—O2 | 119.3 (2) | N1—P1—O1 | 110.52 (11) |
C12—C7—O2 | 118.6 (2) | N3—P1—O1 | 111.13 (11) |
C7—C8—C9 | 118.7 (3) | O2—P1—O1 | 94.31 (9) |
C10—C9—C8 | 120.4 (3) | N2—P2—O3 | 109.11 (12) |
C9—C10—C11 | 119.9 (3) | N2—P2—N1 | 117.16 (11) |
C10—C11—C12 | 120.2 (3) | O3—P2—N1 | 106.41 (12) |
C7—C12—C11 | 118.7 (3) | N2—P2—N4 | 109.75 (12) |
O3—C13—C14 | 111.0 (2) | O3—P2—N4 | 101.20 (11) |
C13—C14—C15 | 112.7 (2) | N1—P2—N4 | 111.92 (12) |
N4—C15—C14 | 109.5 (2) | O4—P3—N2 | 108.37 (11) |
C15—N4—P2 | 114.82 (19) | O4—P3—N3 | 107.64 (12) |
O4—C16—C17 | 110.3 (2) | N2—P3—N3 | 117.90 (12) |
C18—C17—C16 | 112.8 (2) | O4—P3—N5 | 100.61 (11) |
N5—C18—C17 | 109.6 (2) | N2—P3—N5 | 109.91 (12) |
C18—N5—P3 | 113.47 (18) | N3—P3—N5 | 110.93 (12) |
P1—N1—P2 | 123.40 (14) |
C18H24N5O4P3 | F(000) = 488 |
Mr = 467.33 | Dx = 1.470 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.3073 (1) Å | Cell parameters from 10282 reflections |
b = 17.6438 (4) Å | θ = 2.9–27.5° |
c = 9.5481 (2) Å | µ = 0.32 mm−1 |
β = 96.552 (1)° | T = 120 K |
V = 1055.62 (4) Å3 | Plate, colourless |
Z = 2 | 0.22 × 0.18 × 0.04 mm |
Bruker-Nonius APEX2 Area Detector diffractometer | 4543 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 4430 reflections with I > 2σ(I) |
10cm confocal mirrors monochromator | Rint = 0.030 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.2° |
φ and ω scans | h = −8→8 |
Absorption correction: multi-scan SADABS V2.10 (Sheldrick, G.M., 2003) | k = −22→22 |
Tmin = 0.933, Tmax = 0.987 | l = −10→12 |
12391 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.065 | w = 1/[σ2(Fo2) + (0.0168P)2 + 0.620P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.002 |
4543 reflections | Δρmax = 0.26 e Å−3 |
279 parameters | Δρmin = −0.29 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.02 (6) |
C18H24N5O4P3 | V = 1055.62 (4) Å3 |
Mr = 467.33 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 6.3073 (1) Å | µ = 0.32 mm−1 |
b = 17.6438 (4) Å | T = 120 K |
c = 9.5481 (2) Å | 0.22 × 0.18 × 0.04 mm |
β = 96.552 (1)° |
Bruker-Nonius APEX2 Area Detector diffractometer | 4543 independent reflections |
Absorption correction: multi-scan SADABS V2.10 (Sheldrick, G.M., 2003) | 4430 reflections with I > 2σ(I) |
Tmin = 0.933, Tmax = 0.987 | Rint = 0.030 |
12391 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.065 | Δρmax = 0.26 e Å−3 |
S = 1.01 | Δρmin = −0.29 e Å−3 |
4543 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
279 parameters | Absolute structure parameter: 0.02 (6) |
1 restraint |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
H5N | 0.060 (8) | 0.2157 (15) | 0.767 (4) | 0.011 (13)* | |
H4N | 0.824 (6) | 0.325 (4) | 0.650 (4) | 0.05 (2)* | |
C1 | 0.5718 (8) | 0.5162 (3) | 1.0131 (5) | 0.0240 (11) | |
C2 | 0.7612 (9) | 0.4796 (3) | 0.9996 (5) | 0.0252 (11) | |
H2 | 0.7772 | 0.4498 | 0.9185 | 0.030* | |
C3 | 0.9284 (9) | 0.4870 (3) | 1.1067 (6) | 0.0331 (13) | |
H3 | 1.0595 | 0.4615 | 1.0990 | 0.040* | |
C4 | 0.9071 (10) | 0.5309 (4) | 1.2245 (6) | 0.0371 (14) | |
H4 | 1.0233 | 0.5365 | 1.2964 | 0.044* | |
C5 | 0.7132 (11) | 0.5666 (3) | 1.2361 (6) | 0.0364 (14) | |
H5 | 0.6955 | 0.5958 | 1.3177 | 0.044* | |
C6 | 0.5471 (10) | 0.5600 (3) | 1.1303 (6) | 0.0326 (13) | |
H6 | 0.4158 | 0.5853 | 1.1377 | 0.039* | |
C7 | 0.0591 (8) | 0.5483 (3) | 0.6743 (5) | 0.0218 (10) | |
C8 | −0.1485 (8) | 0.5741 (3) | 0.6558 (5) | 0.0240 (11) | |
H8 | −0.2590 | 0.5452 | 0.6899 | 0.029* | |
C9 | −0.1957 (8) | 0.6417 (3) | 0.5880 (5) | 0.0246 (11) | |
H9 | −0.3388 | 0.6596 | 0.5764 | 0.030* | |
C10 | −0.0366 (8) | 0.6839 (3) | 0.5366 (5) | 0.0251 (11) | |
H10 | −0.0698 | 0.7306 | 0.4893 | 0.030* | |
C11 | 0.1725 (9) | 0.6574 (3) | 0.5549 (6) | 0.0325 (13) | |
H11 | 0.2828 | 0.6865 | 0.5209 | 0.039* | |
C12 | 0.2213 (9) | 0.5895 (3) | 0.6216 (6) | 0.0290 (12) | |
H12 | 0.3638 | 0.5710 | 0.6317 | 0.035* | |
C13 | 0.4031 (9) | 0.3921 (3) | 0.3723 (5) | 0.0274 (12) | |
H13A | 0.4094 | 0.4458 | 0.4029 | 0.033* | |
H13B | 0.2960 | 0.3879 | 0.2882 | 0.033* | |
C14 | 0.6196 (8) | 0.3674 (3) | 0.3349 (6) | 0.0298 (12) | |
H14A | 0.6594 | 0.3984 | 0.2553 | 0.036* | |
H14B | 0.6134 | 0.3136 | 0.3050 | 0.036* | |
C15 | 0.7891 (8) | 0.3770 (3) | 0.4632 (5) | 0.0257 (11) | |
H15A | 0.9295 | 0.3592 | 0.4393 | 0.031* | |
H15B | 0.8024 | 0.4313 | 0.4895 | 0.031* | |
C16 | 0.2693 (9) | 0.2276 (4) | 1.0966 (5) | 0.0314 (13) | |
H16A | 0.2493 | 0.2756 | 1.1471 | 0.038* | |
H16B | 0.3492 | 0.1922 | 1.1639 | 0.038* | |
C17 | 0.0529 (9) | 0.1938 (3) | 1.0471 (5) | 0.0291 (12) | |
H17A | −0.0293 | 0.1876 | 1.1289 | 0.035* | |
H17B | 0.0724 | 0.1429 | 1.0065 | 0.035* | |
C18 | −0.0730 (9) | 0.2438 (3) | 0.9365 (6) | 0.0288 (12) | |
H18A | −0.2118 | 0.2194 | 0.9050 | 0.035* | |
H18B | −0.1025 | 0.2933 | 0.9794 | 0.035* | |
N1 | 0.4701 (7) | 0.4303 (2) | 0.6981 (4) | 0.0225 (9) | |
N2 | 0.4243 (7) | 0.2792 (3) | 0.7259 (4) | 0.0226 (9) | |
N3 | 0.2623 (7) | 0.3763 (3) | 0.9082 (5) | 0.0271 (10) | |
O3 | 0.3398 (5) | 0.3445 (2) | 0.4854 (3) | 0.0244 (8) | |
O4 | 0.3944 (6) | 0.2423 (2) | 0.9801 (4) | 0.0251 (8) | |
O1 | 0.3971 (6) | 0.5162 (2) | 0.9090 (3) | 0.0245 (8) | |
O2 | 0.0902 (6) | 0.4801 (2) | 0.7469 (4) | 0.0239 (8) | |
N4 | 0.7256 (7) | 0.3328 (3) | 0.5827 (4) | 0.0236 (9) | |
N5 | 0.0454 (7) | 0.2567 (2) | 0.8122 (5) | 0.0263 (10) | |
P1 | 0.3157 (2) | 0.44552 (9) | 0.81351 (13) | 0.0207 (3) | |
P2 | 0.4893 (2) | 0.34742 (9) | 0.63165 (13) | 0.0201 (3) | |
P3 | 0.2884 (2) | 0.29211 (9) | 0.85345 (13) | 0.0209 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.025 (3) | 0.024 (3) | 0.022 (2) | −0.009 (2) | 0.003 (2) | 0.000 (2) |
C2 | 0.030 (3) | 0.027 (3) | 0.019 (2) | 0.000 (2) | 0.002 (2) | 0.003 (2) |
C3 | 0.032 (3) | 0.034 (3) | 0.032 (3) | −0.006 (3) | −0.002 (2) | 0.011 (2) |
C4 | 0.045 (4) | 0.037 (3) | 0.027 (3) | −0.014 (3) | −0.009 (2) | 0.004 (2) |
C5 | 0.053 (4) | 0.030 (3) | 0.026 (3) | −0.003 (3) | 0.005 (3) | −0.003 (2) |
C6 | 0.032 (3) | 0.032 (3) | 0.034 (3) | −0.001 (3) | 0.003 (2) | −0.004 (2) |
C7 | 0.020 (3) | 0.018 (2) | 0.027 (2) | 0.002 (2) | 0.003 (2) | −0.001 (2) |
C8 | 0.016 (3) | 0.034 (3) | 0.022 (2) | 0.001 (2) | 0.0041 (19) | −0.001 (2) |
C9 | 0.021 (3) | 0.032 (3) | 0.021 (2) | 0.001 (2) | 0.002 (2) | −0.003 (2) |
C10 | 0.025 (3) | 0.024 (3) | 0.024 (2) | 0.003 (2) | −0.004 (2) | 0.003 (2) |
C11 | 0.025 (3) | 0.026 (3) | 0.046 (3) | −0.009 (2) | 0.005 (2) | 0.012 (2) |
C12 | 0.019 (3) | 0.028 (3) | 0.041 (3) | −0.001 (2) | 0.006 (2) | 0.004 (2) |
C13 | 0.029 (3) | 0.031 (3) | 0.021 (2) | −0.001 (2) | −0.004 (2) | 0.005 (2) |
C14 | 0.027 (3) | 0.034 (3) | 0.029 (3) | −0.005 (2) | 0.004 (2) | −0.004 (2) |
C15 | 0.026 (3) | 0.027 (3) | 0.024 (3) | −0.003 (2) | 0.005 (2) | 0.004 (2) |
C16 | 0.028 (3) | 0.044 (3) | 0.022 (2) | 0.000 (3) | 0.002 (2) | 0.011 (2) |
C17 | 0.026 (3) | 0.036 (3) | 0.026 (3) | −0.005 (2) | 0.006 (2) | 0.004 (2) |
C18 | 0.025 (3) | 0.031 (3) | 0.031 (3) | 0.000 (2) | 0.004 (2) | 0.009 (2) |
N1 | 0.017 (2) | 0.024 (2) | 0.026 (2) | 0.0025 (17) | −0.0010 (16) | 0.0050 (17) |
N2 | 0.019 (2) | 0.025 (2) | 0.024 (2) | 0.0000 (17) | 0.0055 (17) | 0.0034 (17) |
N3 | 0.023 (2) | 0.026 (2) | 0.032 (2) | −0.0002 (19) | 0.0017 (19) | 0.0056 (19) |
O3 | 0.0213 (18) | 0.0297 (19) | 0.0208 (16) | −0.0038 (16) | −0.0037 (13) | −0.0007 (15) |
O4 | 0.0211 (19) | 0.028 (2) | 0.0259 (18) | 0.0004 (16) | 0.0017 (14) | 0.0087 (15) |
O1 | 0.026 (2) | 0.0230 (19) | 0.0241 (17) | 0.0017 (15) | −0.0014 (14) | −0.0024 (14) |
O2 | 0.0207 (19) | 0.0194 (18) | 0.0318 (19) | 0.0012 (15) | 0.0036 (14) | 0.0030 (15) |
N4 | 0.015 (2) | 0.033 (3) | 0.023 (2) | −0.0015 (18) | 0.0042 (17) | 0.0011 (18) |
N5 | 0.023 (2) | 0.026 (2) | 0.028 (2) | −0.001 (2) | −0.0018 (18) | 0.0024 (19) |
P1 | 0.0203 (6) | 0.0191 (6) | 0.0225 (6) | 0.0006 (5) | 0.0021 (5) | 0.0006 (5) |
P2 | 0.0178 (6) | 0.0216 (7) | 0.0207 (6) | 0.0012 (5) | 0.0006 (5) | 0.0003 (5) |
P3 | 0.0201 (7) | 0.0188 (6) | 0.0236 (6) | 0.0005 (5) | 0.0015 (5) | 0.0029 (5) |
C1—C2 | 1.375 (8) | C15—N4 | 1.473 (6) |
C1—C6 | 1.382 (8) | C16—O4 | 1.457 (6) |
C1—O1 | 1.395 (6) | C16—C17 | 1.513 (8) |
C2—C3 | 1.387 (7) | C17—C18 | 1.527 (7) |
C3—C4 | 1.384 (8) | C18—N5 | 1.488 (7) |
C4—C5 | 1.390 (9) | N1—P1 | 1.573 (4) |
C5—C6 | 1.374 (8) | N1—P2 | 1.602 (4) |
C7—C8 | 1.378 (7) | N2—P3 | 1.582 (4) |
C7—O2 | 1.390 (6) | N2—P2 | 1.583 (4) |
C7—C12 | 1.394 (7) | N3—P1 | 1.577 (5) |
C8—C9 | 1.371 (7) | N3—P3 | 1.588 (5) |
C9—C10 | 1.382 (7) | O3—P2 | 1.593 (3) |
C10—C11 | 1.390 (8) | O4—P3 | 1.578 (3) |
C11—C12 | 1.374 (8) | O1—P1 | 1.593 (4) |
C13—O3 | 1.458 (6) | O2—P1 | 1.608 (4) |
C13—C14 | 1.513 (7) | N4—P2 | 1.631 (4) |
C14—C15 | 1.539 (7) | N5—P3 | 1.658 (5) |
C2—C1—C6 | 121.1 (5) | C13—O3—P2 | 116.4 (3) |
C2—C1—O1 | 123.8 (4) | C16—O4—P3 | 117.7 (3) |
C6—C1—O1 | 115.0 (5) | C1—O1—P1 | 125.7 (3) |
C1—C2—C3 | 118.8 (5) | C7—O2—P1 | 126.3 (3) |
C4—C3—C2 | 121.0 (6) | C15—N4—P2 | 118.3 (4) |
C3—C4—C5 | 119.1 (5) | C18—N5—P3 | 113.7 (3) |
C6—C5—C4 | 120.4 (5) | N1—P1—N3 | 117.2 (2) |
C5—C6—C1 | 119.7 (6) | N1—P1—O1 | 110.4 (2) |
C8—C7—O2 | 115.4 (4) | N3—P1—O1 | 110.7 (2) |
C8—C7—C12 | 120.3 (5) | N1—P1—O2 | 112.2 (2) |
O2—C7—C12 | 124.3 (5) | N3—P1—O2 | 106.5 (2) |
C9—C8—C7 | 120.0 (5) | O1—P1—O2 | 98.18 (19) |
C8—C9—C10 | 120.5 (5) | N2—P2—O3 | 107.9 (2) |
C9—C10—C11 | 119.3 (5) | N2—P2—N1 | 115.6 (2) |
C12—C11—C10 | 120.6 (5) | O3—P2—N1 | 108.2 (2) |
C11—C12—C7 | 119.2 (5) | N2—P2—N4 | 110.3 (2) |
O3—C13—C14 | 109.8 (4) | O3—P2—N4 | 102.2 (2) |
C13—C14—C15 | 110.1 (4) | N1—P2—N4 | 111.7 (2) |
N4—C15—C14 | 109.4 (4) | O4—P3—N2 | 106.9 (2) |
O4—C16—C17 | 112.2 (4) | O4—P3—N3 | 108.5 (2) |
C16—C17—C18 | 111.5 (5) | N2—P3—N3 | 118.2 (2) |
N5—C18—C17 | 111.8 (4) | O4—P3—N5 | 105.7 (2) |
P1—N1—P2 | 120.9 (3) | N2—P3—N5 | 109.2 (2) |
P3—N2—P2 | 121.7 (3) | N3—P3—N5 | 107.6 (2) |
P1—N3—P3 | 119.9 (3) |
Experimental details
(3a) | (3b) | (5) | (5a) | |
Crystal data | ||||
Chemical formula | C18H24N5O2P3S2 | C18H24N5O2P3S2 | C18H24N5O4P3 | C18H24N5O4P3 |
Mr | 499.45 | 499.45 | 467.33 | 467.33 |
Crystal system, space group | Tetragonal, P41 | Tetragonal, P43 | Orthorhombic, Pbcn | Trigonal, P32 |
Temperature (K) | 120 | 120 | 120 | 120 |
a, b, c (Å) | 11.4912 (1), 11.4912 (1), 16.7890 (2) | 11.4899 (1), 11.4899 (1), 16.7827 (2) | 38.7541 (16), 10.1505 (4), 10.5550 (5) | 10.4920 (1), 10.4920 (1), 16.6645 (3) |
α, β, γ (°) | 90, 90, 90 | 90, 90, 90 | 90, 90, 90 | 90, 90, 120 |
V (Å3) | 2216.95 (4) | 2215.62 (4) | 4152.1 (3) | 1588.69 (4) |
Z | 4 | 4 | 8 | 3 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.48 | 0.48 | 0.32 | 0.32 |
Crystal size (mm) | 0.45 × 0.45 × 0.40 | 0.55 × 0.20 × 0.20 | 0.65 × 0.02 × 0.01 | 0.50 × 0.40 × 0.34 |
Data collection | ||||
Diffractometer | Bruker-Nonius KappaCCD Area Detector diffractometer | Bruker-Nonius KappaCCD Area Detector diffractometer | Bruker APEX2 diffractometer | Bruker-Nonius KappaCCD Area Detector diffractometer |
Absorption correction | Multi-scan SADABS V2.10 (Sheldrick, G.M., 2003) | Multi-scan SADABS V2.10 (Sheldrick, G.M., 2003) | Multi-scan SADABS V2.10 (Sheldrick, G.M., 2003) | Multi-scan SADABS V2.10 (Sheldrick, G.M., 2003) |
Tmin, Tmax | 0.812, 0.830 | 0.777, 0.910 | 0.817, 0.997 | 0.858, 0.900 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 41619, 5057, 4976 | 15809, 4532, 4330 | 19961, 4703, 3961 | 4871, 4848, 4802 |
Rint | 0.031 | 0.035 | 0.055 | 0.048 |
(sin θ/λ)max (Å−1) | 0.650 | 0.649 | 0.650 | 0.649 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.019, 0.049, 1.04 | 0.028, 0.066, 1.03 | 0.062, 0.135, 1.08 | 0.029, 0.072, 1.02 |
No. of reflections | 5057 | 4532 | 4703 | 4848 |
No. of parameters | 279 | 279 | 279 | 280 |
No. of restraints | 1 | 1 | 0 | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
w = 1/[σ2(Fo2) + (0.0283P)2 + 0.4819P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0282P)2 + 0.916P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.P)2 + 15.046P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0389P)2 + 0.8904P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.16, −0.27 | 0.19, −0.33 | 0.55, −0.43 | 0.18, −0.38 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 | ? | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | 0.01 (4) | −0.01 (5) | ? | −0.06 (8) |
(5b) | |
Crystal data | |
Chemical formula | C18H24N5O4P3 |
Mr | 467.33 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 120 |
a, b, c (Å) | 6.3073 (1), 17.6438 (4), 9.5481 (2) |
α, β, γ (°) | 90, 96.552 (1), 90 |
V (Å3) | 1055.62 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.32 |
Crystal size (mm) | 0.22 × 0.18 × 0.04 |
Data collection | |
Diffractometer | Bruker-Nonius APEX2 Area Detector diffractometer |
Absorption correction | Multi-scan SADABS V2.10 (Sheldrick, G.M., 2003) |
Tmin, Tmax | 0.933, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12391, 4543, 4430 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.065, 1.01 |
No. of reflections | 4543 |
No. of parameters | 279 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
w = 1/[σ2(Fo2) + (0.0168P)2 + 0.620P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.26, −0.29 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | 0.02 (6) |
Computer programs: DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998), DENZO, COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON (Spek, 1990).