Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113005325/fa3310sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113005325/fa3310Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113005325/fa3310IIsup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113005325/fa3310Isup4.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113005325/fa3310IIsup5.cml |
CCDC references: 934614; 934615
For both compounds, data collection: APEX2 (Bruker, 2011); cell refinement: APEX2 and SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
C11H11BrO3 | Dx = 1.786 Mg m−3 |
Mr = 271.11 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P421c | Cell parameters from 3775 reflections |
Hall symbol: P -4 2n | θ = 2.5–24.6° |
a = 16.2247 (19) Å | µ = 4.06 mm−1 |
c = 7.6586 (8) Å | T = 91 K |
V = 2016.1 (4) Å3 | Rectangular block, colourless |
Z = 8 | 0.25 × 0.13 × 0.13 mm |
F(000) = 1088 |
Bruker APEXII CCD area-detector diffractometer | 1715 independent reflections |
Radiation source: fine-focus sealed tube | 1615 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ω scans | θmax = 24.8°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2011) | h = −19→15 |
Tmin = 0.579, Tmax = 0.745 | k = −14→19 |
9841 measured reflections | l = −9→6 |
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)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.078 | w = 1/[σ2(Fo2) + (0.0336P)2 + 1.9393P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.001 |
1715 reflections | Δρmax = 0.47 e Å−3 |
141 parameters | Δρmin = −0.32 e Å−3 |
7 restraints | Absolute structure: Flack (1983), with 717 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.023 (15) |
Experimental. ADDITIONAL EXPERIMENTAL & CHARACTERISATION DETAILS Bromotrimethylquinone: 70% yield. 1H NMR (400 MHz, CDCl3, δ, p.p.m.): 2.04 (s, 3H, CH3), 2.08 (s, 3H, CH3), 2.21 (s, 3H, CH3); 13C NMR (100 MHz, CDCl3, δ, p.p.m.): 12.6, 13.2, 17.1, 135.4, 140.7, 140.9, 145.6, 179.4, 184.4. Methyl 5-bromo-6-hydroxy-7,8-dimethyl-2-oxochroman-3-carboxylate: 76% yield. 1H NMR (400 MHz, CDCl3, δ, p.p.m.): 2.20 (s, 3H, CH3), 2.24 (s, 3H, CH3), 3.23 (dd, J = 4 and 16 Hz, 1H, CH), 3.45 (dd, J = 8 and 16 Hz, 1H, CH), 3.76 (m, 1H, CH), 3.37 (s, 3H, OCH3),5.51 (bs, 1H, OH); 13C NMR (100 MHz, CDCl3, δ, p.p.m.): 12.1, 13.0, 20.1, 45.8, 53.1, 107.4, 117.8, 124.3, 125.8, 143.3, 147.2, 164.3, 167.7. HR MS (ESI): calculated for C13H13BrO5: [M]+ m/z 327.9940, found: m/z 327.9682. 5-Bromo-6-hydroxy-7,8-dimethylchroman-2-one, (I), 72% yield. 13C NMR (100 MHz, CDCl3, δ, p.p.m.): 11.8, 12.8, 24.7, 28.8, 107.3, 119.3, 123.6, 125.7, 144.0, 146.8, 168.4. Nitrotrimethylquinone: 60% yield. 1H NMR (400 MHz, CDCl3, δ, p.p.m.): 2.06 (s, 3H, CH3), 2.09 (m, 6H, CH3); 13C NMR (100 MHz, CDCl3, δ, p.p.m.): 11.3, 12.2, 12.8, 134.3, 139.7, 142.2, 150.2, 177.2, 185.5. Methyl 7,8-dimethyl-5-nitro-2,6-dioxo-3,4,6,8a-tetrahydro-2H-chromene- 3-carboxylate: 50% yield. 1H NMR (400 MHz, CDCl3, δ, p.p.m.): 2.28 (s, 3H, CH3), 2.32 (s, 3H, CH3), 3.52 (dd, J = 4 and 16 Hz, 1H, CH), 3.67–3.75 (m, 2H, CH2), 3.77 (s, 3H, OCH3); 13C NMR (100 MHz, CDCl3, δ, p.p.m.): 12.2, 13.4, 25.5, 45.0, 53.3, 114.9, 117.8, 127.8, 135.8, 143.2, 150.5, 163.5, 167.3. HR MS (ESI): calculated for C13H13NO7: [M]+ m/z 295.0686, found: m/z 295.0687. 5-Nitro-6-hydroxy-7,8-dimethylchroman-2-one (II) 66% yield. 13C NMR (100 MHz, CDCl3, δ, p.p.m.): 12.1, 12.6, 23.7, 29.1, 116.8, 127.1, 131.1, 135.7, 143.8, 149.9, 167.5. 6-Hydroxy-7,8-dimethyl-5-(trifluoromethyl)chroman-2-one,(III). 13C NMR (100 MHz, CDCl3, δ, p.p.m.): 12.1, 13.3, 22.2, 28.1, 118.0, 126.2, 132.2, 140.5, 145.2, 148.7, 168.1; 19F NMR (376 MHz, CDCl3, δ, p.p.m.): -79.1. |
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 | ||
O1 | 0.20618 (19) | 0.02966 (18) | 0.4131 (4) | 0.0138 (7) | |
O2 | 0.0990 (2) | −0.04812 (19) | 0.3584 (4) | 0.0196 (8) | |
C2 | 0.1321 (3) | 0.0176 (3) | 0.3337 (6) | 0.0139 (10) | |
C3 | 0.1009 (3) | 0.0836 (3) | 0.2165 (7) | 0.0168 (10) | |
H3A | 0.0400 | 0.0810 | 0.2146 | 0.020* | |
H3B | 0.1206 | 0.0724 | 0.0965 | 0.020* | |
C4 | 0.1266 (2) | 0.1706 (3) | 0.2666 (6) | 0.0147 (10) | |
H4A | 0.1175 | 0.2082 | 0.1666 | 0.018* | |
H4B | 0.0924 | 0.1900 | 0.3654 | 0.018* | |
C5 | 0.2662 (3) | 0.2413 (2) | 0.3011 (6) | 0.0120 (9) | |
Br5 | 0.22113 (3) | 0.34214 (3) | 0.22181 (7) | 0.02019 (16) | |
C6 | 0.3503 (3) | 0.2402 (3) | 0.3475 (6) | 0.0129 (10) | |
O6 | 0.4009 (2) | 0.30533 (19) | 0.3291 (4) | 0.0175 (8) | |
H6O | 0.377 (3) | 0.342 (2) | 0.284 (6) | 0.026* | |
C7 | 0.3844 (3) | 0.1678 (3) | 0.4196 (6) | 0.0125 (10) | |
C71 | 0.4768 (2) | 0.1693 (3) | 0.4774 (5) | 0.0054 (9) | |
H71A | 0.4810 | 0.1523 | 0.5998 | 0.008* | |
H71B | 0.4986 | 0.2253 | 0.4644 | 0.008* | |
H71C | 0.5086 | 0.1314 | 0.4042 | 0.008* | |
C8 | 0.3351 (3) | 0.0981 (3) | 0.4391 (6) | 0.0118 (10) | |
C81 | 0.3700 (3) | 0.0164 (3) | 0.5104 (6) | 0.0098 (10) | |
H81A | 0.3989 | −0.0128 | 0.4168 | 0.015* | |
H81B | 0.3247 | −0.0178 | 0.5540 | 0.015* | |
H81C | 0.4085 | 0.0280 | 0.6059 | 0.015* | |
C9 | 0.2528 (3) | 0.1024 (3) | 0.3874 (6) | 0.0134 (10) | |
C10 | 0.2159 (3) | 0.1724 (3) | 0.3178 (5) | 0.0111 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0118 (17) | 0.0080 (16) | 0.0218 (17) | −0.0011 (14) | −0.0016 (15) | 0.0034 (13) |
O2 | 0.0179 (18) | 0.0118 (18) | 0.0291 (19) | −0.0020 (14) | 0.0033 (16) | −0.0020 (15) |
C2 | 0.014 (3) | 0.016 (3) | 0.011 (2) | 0.001 (2) | 0.0053 (19) | −0.0043 (19) |
C3 | 0.014 (2) | 0.017 (2) | 0.020 (2) | −0.0031 (19) | 0.001 (2) | 0.000 (2) |
C4 | 0.007 (2) | 0.018 (2) | 0.019 (2) | 0.0015 (17) | 0.001 (2) | 0.002 (2) |
C5 | 0.013 (2) | 0.009 (2) | 0.013 (2) | 0.0015 (18) | −0.002 (2) | 0.002 (2) |
Br5 | 0.0211 (3) | 0.0144 (3) | 0.0250 (3) | 0.00195 (19) | 0.0010 (2) | 0.0031 (2) |
C6 | 0.013 (2) | 0.015 (2) | 0.011 (2) | 0.0016 (19) | 0.003 (2) | −0.0018 (18) |
O6 | 0.0148 (18) | 0.0153 (18) | 0.0223 (19) | −0.0047 (14) | −0.0046 (15) | 0.0031 (15) |
C7 | 0.015 (2) | 0.013 (2) | 0.010 (2) | 0.003 (2) | 0.001 (2) | 0.000 (2) |
C71 | 0.0053 (12) | 0.0054 (12) | 0.0054 (12) | −0.0004 (9) | 0.0018 (9) | 0.0002 (9) |
C8 | 0.009 (2) | 0.016 (2) | 0.011 (2) | 0.003 (2) | 0.001 (2) | −0.002 (2) |
C81 | 0.008 (2) | 0.011 (2) | 0.010 (2) | −0.0035 (19) | 0.0010 (19) | −0.0003 (19) |
C9 | 0.020 (3) | 0.008 (2) | 0.012 (2) | −0.0031 (19) | 0.005 (2) | −0.0022 (19) |
C10 | 0.013 (2) | 0.013 (2) | 0.008 (2) | 0.0033 (19) | −0.0010 (19) | −0.0038 (18) |
O1—C2 | 1.361 (6) | C6—C7 | 1.411 (6) |
O1—C9 | 1.416 (5) | O6—H6O | 0.794 (19) |
O2—C2 | 1.209 (5) | C7—C8 | 1.392 (6) |
C2—C3 | 1.486 (6) | C7—C71 | 1.563 (6) |
C3—C4 | 1.520 (6) | C71—H71A | 0.9800 |
C3—H3A | 0.9900 | C71—H71B | 0.9800 |
C3—H3B | 0.9900 | C71—H71C | 0.9800 |
C4—C10 | 1.500 (6) | C8—C9 | 1.395 (6) |
C4—H4A | 0.9900 | C8—C81 | 1.541 (6) |
C4—H4B | 0.9900 | C81—H81A | 0.9800 |
C5—C10 | 1.390 (6) | C81—H81B | 0.9800 |
C5—C6 | 1.409 (6) | C81—H81C | 0.9800 |
C5—Br5 | 1.892 (4) | C9—C10 | 1.390 (6) |
C6—O6 | 1.347 (5) | ||
C2—O1—C9 | 121.9 (3) | C8—C7—C71 | 122.3 (4) |
O2—C2—O1 | 116.7 (4) | C6—C7—C71 | 118.3 (4) |
O2—C2—C3 | 125.4 (4) | C7—C71—H71A | 109.5 |
O1—C2—C3 | 117.8 (4) | C7—C71—H71B | 109.5 |
C2—C3—C4 | 115.0 (4) | H71A—C71—H71B | 109.5 |
C2—C3—H3A | 108.5 | C7—C71—H71C | 109.5 |
C4—C3—H3A | 108.5 | H71A—C71—H71C | 109.5 |
C2—C3—H3B | 108.5 | H71B—C71—H71C | 109.5 |
C4—C3—H3B | 108.5 | C7—C8—C9 | 118.6 (4) |
H3A—C3—H3B | 107.5 | C7—C8—C81 | 121.7 (4) |
C10—C4—C3 | 110.4 (3) | C9—C8—C81 | 119.6 (4) |
C10—C4—H4A | 109.6 | C8—C81—H81A | 109.5 |
C3—C4—H4A | 109.6 | C8—C81—H81B | 109.5 |
C10—C4—H4B | 109.6 | H81A—C81—H81B | 109.5 |
C3—C4—H4B | 109.6 | C8—C81—H81C | 109.5 |
H4A—C4—H4B | 108.1 | H81A—C81—H81C | 109.5 |
C10—C5—C6 | 122.3 (4) | H81B—C81—H81C | 109.5 |
C10—C5—Br5 | 119.8 (3) | C10—C9—C8 | 124.2 (4) |
C6—C5—Br5 | 117.8 (3) | C10—C9—O1 | 120.3 (4) |
O6—C6—C5 | 123.6 (4) | C8—C9—O1 | 115.5 (4) |
O6—C6—C7 | 117.1 (4) | C5—C10—C9 | 116.0 (4) |
C5—C6—C7 | 119.3 (4) | C5—C10—C4 | 124.0 (4) |
C6—O6—H6O | 110 (4) | C9—C10—C4 | 120.0 (4) |
C8—C7—C6 | 119.5 (4) | ||
C9—O1—C2—O2 | 176.9 (4) | C7—C8—C9—C10 | −0.4 (7) |
C9—O1—C2—C3 | 0.3 (6) | C81—C8—C9—C10 | −178.5 (4) |
O2—C2—C3—C4 | 152.6 (4) | C7—C8—C9—O1 | −179.2 (4) |
O1—C2—C3—C4 | −31.2 (6) | C81—C8—C9—O1 | 2.7 (6) |
C2—C3—C4—C10 | 43.1 (5) | C2—O1—C9—C10 | 16.8 (6) |
C10—C5—C6—O6 | 178.5 (4) | C2—O1—C9—C8 | −164.3 (4) |
Br5—C5—C6—O6 | −3.9 (6) | C6—C5—C10—C9 | 1.5 (6) |
C10—C5—C6—C7 | −2.4 (6) | Br5—C5—C10—C9 | −176.0 (3) |
Br5—C5—C6—C7 | 175.2 (3) | C6—C5—C10—C4 | −178.7 (4) |
O6—C6—C7—C8 | −179.0 (4) | Br5—C5—C10—C4 | 3.7 (6) |
C5—C6—C7—C8 | 1.8 (7) | C8—C9—C10—C5 | −0.1 (6) |
O6—C6—C7—C71 | 1.8 (6) | O1—C9—C10—C5 | 178.6 (4) |
C5—C6—C7—C71 | −177.4 (4) | C8—C9—C10—C4 | −179.9 (4) |
C6—C7—C8—C9 | −0.4 (7) | O1—C9—C10—C4 | −1.1 (6) |
C71—C7—C8—C9 | 178.7 (4) | C3—C4—C10—C5 | 152.4 (4) |
C6—C7—C8—C81 | 177.6 (4) | C3—C4—C10—C9 | −27.9 (6) |
C71—C7—C8—C81 | −3.2 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6O···Br5 | 0.79 (2) | 2.57 (4) | 3.089 (3) | 124 (4) |
O6—H6O···O2i | 0.79 (2) | 2.12 (4) | 2.778 (4) | 140 (5) |
C3—H3A···O2ii | 0.99 | 2.57 | 3.469 (6) | 152 |
C4—H4B···O1iii | 0.99 | 2.62 | 3.575 (6) | 162 |
C4—H4B···O2iii | 0.99 | 2.68 | 3.349 (6) | 125 |
C3—H3B···O6iv | 0.99 | 2.41 | 3.343 (6) | 156 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x, −y, z; (iii) −y, x, −z+1; (iv) −y+1/2, −x+1/2, z−1/2. |
C11H11NO5 | Z = 2 |
Mr = 237.21 | F(000) = 248 |
Triclinic, P1 | Dx = 1.552 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.0922 (12) Å | Cell parameters from 1620 reflections |
b = 7.3347 (15) Å | θ = 3.0–27.4° |
c = 13.942 (3) Å | µ = 0.12 mm−1 |
α = 97.657 (12)° | T = 93 K |
β = 100.072 (11)° | Plate, yellow |
γ = 90.862 (12)° | 0.43 × 0.17 × 0.05 mm |
V = 507.75 (19) Å3 |
Bruker APEXII CCD area-detector diffractometer | 2317 independent reflections |
Radiation source: fine-focus sealed tube | 1367 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.300 |
ω scans | θmax = 27.5°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2011) | h = −6→6 |
Tmin = 0.649, Tmax = 0.746 | k = −9→8 |
7686 measured reflections | l = −17→18 |
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)] = 0.076 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.204 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0872P)2] where P = (Fo2 + 2Fc2)/3 |
2317 reflections | (Δ/σ)max < 0.001 |
160 parameters | Δρmax = 0.55 e Å−3 |
0 restraints | Δρmin = −0.49 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 | ||
O1 | 0.5980 (3) | 0.5812 (2) | 0.88673 (12) | 0.0211 (5) | |
O2 | 0.7046 (3) | 0.7507 (3) | 1.03108 (14) | 0.0278 (5) | |
C2 | 0.5337 (5) | 0.7046 (4) | 0.96087 (19) | 0.0211 (6) | |
C3 | 0.2542 (5) | 0.7678 (4) | 0.9441 (2) | 0.0241 (6) | |
H3A | 0.2431 | 0.8830 | 0.9890 | 0.029* | |
H3B | 0.1338 | 0.6736 | 0.9602 | 0.029* | |
C4 | 0.1604 (5) | 0.8018 (4) | 0.83830 (19) | 0.0218 (6) | |
H4A | −0.0314 | 0.8295 | 0.8281 | 0.026* | |
H4B | 0.2619 | 0.9085 | 0.8245 | 0.026* | |
C5 | 0.0373 (5) | 0.5664 (3) | 0.68000 (19) | 0.0192 (6) | |
N5 | −0.1732 (4) | 0.6805 (3) | 0.63995 (16) | 0.0209 (5) | |
O51 | −0.3682 (3) | 0.6060 (3) | 0.58054 (14) | 0.0251 (5) | |
O52 | −0.1494 (4) | 0.8473 (3) | 0.66469 (14) | 0.0307 (5) | |
C6 | 0.0720 (5) | 0.3954 (3) | 0.62688 (18) | 0.0180 (6) | |
O6 | −0.0884 (3) | 0.3227 (3) | 0.54185 (13) | 0.0222 (5) | |
H6O | −0.223 (6) | 0.393 (4) | 0.541 (2) | 0.033* | |
C7 | 0.2890 (5) | 0.2897 (3) | 0.66103 (19) | 0.0178 (6) | |
C71 | 0.3268 (5) | 0.1090 (4) | 0.6017 (2) | 0.0240 (6) | |
H71A | 0.3359 | 0.0113 | 0.6436 | 0.036* | |
H71B | 0.4930 | 0.1157 | 0.5757 | 0.036* | |
H71C | 0.1762 | 0.0820 | 0.5469 | 0.036* | |
C8 | 0.4606 (5) | 0.3538 (3) | 0.74836 (18) | 0.0178 (6) | |
C81 | 0.6915 (5) | 0.2437 (4) | 0.7883 (2) | 0.0219 (6) | |
H81A | 0.7798 | 0.1912 | 0.7344 | 0.033* | |
H81B | 0.6259 | 0.1441 | 0.8193 | 0.033* | |
H81C | 0.8193 | 0.3240 | 0.8371 | 0.033* | |
C9 | 0.4106 (5) | 0.5231 (3) | 0.80064 (19) | 0.0176 (6) | |
C10 | 0.2038 (5) | 0.6325 (3) | 0.77009 (19) | 0.0190 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0141 (9) | 0.0273 (10) | 0.0217 (11) | 0.0010 (7) | 0.0036 (7) | 0.0019 (8) |
O2 | 0.0191 (9) | 0.0378 (12) | 0.0254 (11) | −0.0019 (8) | 0.0033 (8) | 0.0016 (9) |
C2 | 0.0203 (12) | 0.0248 (14) | 0.0205 (15) | −0.0032 (10) | 0.0085 (11) | 0.0053 (12) |
C3 | 0.0206 (13) | 0.0299 (15) | 0.0240 (15) | 0.0025 (11) | 0.0097 (11) | 0.0044 (12) |
C4 | 0.0187 (12) | 0.0240 (14) | 0.0236 (15) | 0.0025 (10) | 0.0043 (11) | 0.0051 (12) |
C5 | 0.0146 (12) | 0.0216 (14) | 0.0236 (15) | 0.0020 (10) | 0.0073 (10) | 0.0063 (12) |
N5 | 0.0203 (11) | 0.0237 (12) | 0.0211 (12) | 0.0041 (9) | 0.0085 (9) | 0.0048 (10) |
O51 | 0.0149 (9) | 0.0313 (11) | 0.0278 (11) | 0.0003 (7) | 0.0004 (7) | 0.0037 (9) |
O52 | 0.0343 (11) | 0.0246 (11) | 0.0316 (12) | 0.0079 (8) | 0.0012 (9) | 0.0036 (9) |
C6 | 0.0171 (12) | 0.0215 (14) | 0.0163 (13) | −0.0025 (10) | 0.0050 (10) | 0.0041 (11) |
O6 | 0.0167 (9) | 0.0254 (11) | 0.0236 (11) | 0.0026 (7) | 0.0018 (8) | 0.0027 (8) |
C7 | 0.0174 (12) | 0.0187 (13) | 0.0200 (14) | 0.0010 (10) | 0.0086 (10) | 0.0052 (11) |
C71 | 0.0237 (13) | 0.0234 (15) | 0.0248 (15) | 0.0031 (11) | 0.0035 (11) | 0.0038 (12) |
C8 | 0.0141 (11) | 0.0221 (14) | 0.0199 (14) | 0.0007 (9) | 0.0076 (10) | 0.0067 (11) |
C81 | 0.0179 (12) | 0.0240 (14) | 0.0251 (15) | 0.0044 (10) | 0.0065 (11) | 0.0042 (12) |
C9 | 0.0157 (11) | 0.0211 (14) | 0.0175 (13) | −0.0009 (10) | 0.0057 (10) | 0.0047 (11) |
C10 | 0.0161 (12) | 0.0203 (14) | 0.0231 (15) | −0.0019 (10) | 0.0091 (10) | 0.0051 (11) |
O1—C2 | 1.369 (3) | O51—O51i | 2.686 (4) |
O1—C9 | 1.409 (3) | C6—O6 | 1.355 (3) |
O2—C2 | 1.198 (3) | C6—C7 | 1.410 (3) |
C2—C3 | 1.492 (4) | O6—H6O | 0.86 (3) |
C3—C4 | 1.524 (4) | C7—C8 | 1.389 (3) |
C3—H3A | 0.9900 | C7—C71 | 1.500 (4) |
C3—H3B | 0.9900 | C71—H71A | 0.9800 |
C4—C10 | 1.504 (4) | C71—H71B | 0.9800 |
C4—H4A | 0.9900 | C71—H71C | 0.9800 |
C4—H4B | 0.9900 | C8—C9 | 1.404 (4) |
C5—C6 | 1.399 (4) | C8—C81 | 1.505 (3) |
C5—C10 | 1.409 (4) | C81—H81A | 0.9800 |
C5—N5 | 1.450 (3) | C81—H81B | 0.9800 |
N5—O52 | 1.225 (3) | C81—H81C | 0.9800 |
N5—O51 | 1.243 (3) | C9—C10 | 1.376 (3) |
C2—O1—C9 | 121.11 (19) | C6—O6—H6O | 101 (2) |
O2—C2—O1 | 117.5 (2) | C8—C7—C6 | 119.7 (2) |
O2—C2—C3 | 127.2 (2) | C8—C7—C71 | 121.7 (2) |
O1—C2—C3 | 115.3 (2) | C6—C7—C71 | 118.6 (2) |
C2—C3—C4 | 112.2 (2) | C7—C71—H71A | 109.5 |
C2—C3—H3A | 109.2 | C7—C71—H71B | 109.5 |
C4—C3—H3A | 109.2 | H71A—C71—H71B | 109.5 |
C2—C3—H3B | 109.2 | C7—C71—H71C | 109.5 |
C4—C3—H3B | 109.2 | H71A—C71—H71C | 109.5 |
H3A—C3—H3B | 107.9 | H71B—C71—H71C | 109.5 |
C10—C4—C3 | 108.9 (2) | C7—C8—C9 | 118.5 (2) |
C10—C4—H4A | 109.9 | C7—C8—C81 | 121.4 (2) |
C3—C4—H4A | 109.9 | C9—C8—C81 | 120.1 (2) |
C10—C4—H4B | 109.9 | C8—C81—H81A | 109.5 |
C3—C4—H4B | 109.9 | C8—C81—H81B | 109.5 |
H4A—C4—H4B | 108.3 | H81A—C81—H81B | 109.5 |
C6—C5—C10 | 122.0 (2) | C8—C81—H81C | 109.5 |
C6—C5—N5 | 118.9 (2) | H81A—C81—H81C | 109.5 |
C10—C5—N5 | 119.1 (2) | H81B—C81—H81C | 109.5 |
O52—N5—O51 | 122.5 (2) | C10—C9—C8 | 124.2 (2) |
O52—N5—C5 | 118.6 (2) | C10—C9—O1 | 120.7 (2) |
O51—N5—C5 | 118.9 (2) | C8—C9—O1 | 115.0 (2) |
N5—O51—O51i | 157.66 (18) | C9—C10—C5 | 116.1 (2) |
O6—C6—C5 | 124.3 (2) | C9—C10—C4 | 118.1 (2) |
O6—C6—C7 | 116.3 (2) | C5—C10—C4 | 125.6 (2) |
C5—C6—C7 | 119.4 (2) |
Symmetry code: (i) −x−1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6O···O51 | 0.86 (3) | 1.80 (3) | 2.588 (3) | 151 (3) |
O6—H6O···O51i | 0.86 (3) | 2.45 (3) | 3.078 (3) | 130 (3) |
C3—H3B···O2ii | 0.99 | 2.59 | 3.245 (3) | 124 |
C81—H81A···O52iii | 0.98 | 2.63 | 3.362 (3) | 131 |
Symmetry codes: (i) −x−1, −y+1, −z+1; (ii) x−1, y, z; (iii) x+1, y−1, z. |