Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768109018898/so5027sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768109018898/so5027Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768109018898/so5027IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768109018898/so5027IIIsup4.hkl |
CCDC references: 746160; 746161; 746162
For all compounds, data collection: Collect (Nonius BV, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: DENZO and Scalepak (Otwinowski & Minor, 1997). Program(s) used to solve structure: known for (I), (II); Packing arguments for (III). Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) for (I), (II); RAELS2006 (Rae, 2006) for (III). For all compounds, molecular graphics: Xtal3.7 (Hall et al., 2001); software used to prepare material for publication: Xtal3.7 (Hall et al., 2001).
C9H11NO2 | F(000) = 352 |
Mr = 165.19 | Dx = 1.211 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 83119 reflections |
a = 8.2570 (7) Å | θ = 2.6–25.0° |
b = 5.5009 (4) Å | µ = 0.09 mm−1 |
c = 19.956 (2) Å | T = 300 K |
β = 91.699 (4)° | Block, colourless |
V = 906.02 (14) Å3 | 0.15 × 0.15 × 0.07 mm |
Z = 4 |
KappaCCD diffractometer | 1595 independent reflections |
Radiation source: fine-focus sealed tube | 1108 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
Detector resolution: 9 pixels mm-1 | θmax = 25.1°, θmin = 3.2° |
CCD scans | h = −9→9 |
Absorption correction: integration Gaussian integration (Coppens, 1970) | k = −6→6 |
Tmin = 0.980, Tmax = 0.989 | l = −23→23 |
12216 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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | All H-atom parameters refined |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0631P)2 + 0.1023P] where P = (Fo2 + 2Fc2)/3 |
1595 reflections | (Δ/σ)max < 0.001 |
153 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.10 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 | 0.47994 (18) | 0.4098 (3) | 0.35998 (7) | 0.0602 (4) | |
C2 | 0.3381 (2) | 0.5278 (3) | 0.37717 (9) | 0.0683 (5) | |
C3 | 0.1889 (2) | 0.4420 (3) | 0.35654 (9) | 0.0700 (5) | |
C4 | 0.17547 (19) | 0.2330 (3) | 0.31754 (7) | 0.0621 (4) | |
C5 | 0.3176 (2) | 0.1155 (3) | 0.29952 (8) | 0.0661 (5) | |
C6 | 0.4662 (2) | 0.2028 (3) | 0.32038 (8) | 0.0656 (5) | |
C7 | 0.6407 (2) | 0.4978 (3) | 0.38208 (8) | 0.0672 (5) | |
O8 | 0.76791 (14) | 0.4103 (2) | 0.36567 (6) | 0.0895 (5) | |
O9 | 0.63403 (13) | 0.6869 (2) | 0.42404 (6) | 0.0802 (4) | |
C10 | 0.7866 (2) | 0.7865 (5) | 0.44921 (13) | 0.0903 (6) | |
C11 | 0.7475 (3) | 0.9811 (5) | 0.49787 (13) | 0.0931 (7) | |
N12 | 0.0263 (2) | 0.1503 (3) | 0.29546 (9) | 0.0831 (5) | |
H13 | 0.347 (2) | 0.668 (3) | 0.4029 (8) | 0.081 (5)* | |
H14 | 0.092 (2) | 0.523 (3) | 0.3709 (8) | 0.078 (5)* | |
H15 | 0.3051 (19) | −0.030 (3) | 0.2739 (8) | 0.074 (5)* | |
H16 | 0.562 (2) | 0.124 (3) | 0.3068 (7) | 0.069 (4)* | |
H17 | 0.842 (3) | 0.838 (4) | 0.4110 (10) | 0.107 (7)* | |
H18 | 0.846 (3) | 0.641 (4) | 0.4707 (10) | 0.112 (7)* | |
H19 | 0.680 (3) | 1.102 (5) | 0.4772 (13) | 0.138 (10)* | |
H20 | 0.848 (3) | 1.059 (4) | 0.5160 (11) | 0.122 (7)* | |
H21 | 0.688 (3) | 0.919 (4) | 0.5369 (13) | 0.137 (9)* | |
H22 | −0.058 (3) | 0.208 (4) | 0.3146 (10) | 0.092 (6)* | |
H23 | 0.023 (2) | −0.001 (4) | 0.2767 (10) | 0.096 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0603 (9) | 0.0598 (9) | 0.0607 (9) | 0.0027 (7) | 0.0036 (7) | 0.0017 (7) |
C2 | 0.0676 (11) | 0.0617 (10) | 0.0753 (11) | 0.0047 (8) | −0.0004 (8) | −0.0102 (9) |
C3 | 0.0599 (10) | 0.0685 (11) | 0.0814 (11) | 0.0103 (8) | −0.0010 (8) | −0.0107 (9) |
C4 | 0.0618 (10) | 0.0613 (9) | 0.0632 (9) | 0.0010 (7) | −0.0017 (7) | 0.0006 (8) |
C5 | 0.0728 (11) | 0.0590 (10) | 0.0668 (10) | 0.0027 (8) | 0.0047 (8) | −0.0078 (8) |
C6 | 0.0620 (10) | 0.0668 (10) | 0.0686 (10) | 0.0078 (8) | 0.0086 (8) | −0.0017 (8) |
C7 | 0.0635 (10) | 0.0715 (11) | 0.0666 (10) | 0.0020 (8) | 0.0040 (8) | 0.0037 (8) |
O8 | 0.0610 (8) | 0.1057 (10) | 0.1022 (10) | 0.0041 (6) | 0.0089 (6) | −0.0169 (8) |
O9 | 0.0646 (7) | 0.0837 (8) | 0.0921 (9) | −0.0049 (6) | −0.0014 (6) | −0.0180 (7) |
C10 | 0.0693 (12) | 0.1033 (16) | 0.0981 (15) | −0.0173 (11) | −0.0007 (11) | −0.0148 (14) |
C11 | 0.0922 (15) | 0.0925 (15) | 0.0937 (16) | −0.0157 (13) | −0.0098 (13) | −0.0112 (13) |
N12 | 0.0660 (10) | 0.0829 (12) | 0.1000 (12) | −0.0003 (8) | −0.0013 (8) | −0.0226 (9) |
C1—C6 | 1.389 (2) | C7—O8 | 1.2097 (18) |
C1—C2 | 1.391 (2) | C7—O9 | 1.3373 (19) |
C1—C7 | 1.468 (2) | O9—C10 | 1.450 (2) |
C2—C3 | 1.371 (2) | C10—C11 | 1.487 (3) |
C2—H13 | 0.927 (17) | C10—H17 | 0.94 (2) |
C3—C4 | 1.391 (2) | C10—H18 | 1.02 (2) |
C3—H14 | 0.965 (17) | C11—H19 | 0.95 (3) |
C4—N12 | 1.373 (2) | C11—H20 | 0.99 (3) |
C4—C5 | 1.397 (2) | C11—H21 | 0.99 (3) |
C5—C6 | 1.370 (2) | N12—H22 | 0.86 (2) |
C5—H15 | 0.954 (17) | N12—H23 | 0.91 (2) |
C6—H16 | 0.951 (16) | ||
C6—C1—C2 | 117.87 (15) | O8—C7—C1 | 124.91 (16) |
C6—C1—C7 | 119.95 (14) | O9—C7—C1 | 113.02 (14) |
C2—C1—C7 | 122.18 (15) | C7—O9—C10 | 117.35 (14) |
C3—C2—C1 | 121.40 (16) | O9—C10—C11 | 107.14 (18) |
C3—C2—H13 | 120.5 (11) | O9—C10—H17 | 105.6 (13) |
C1—C2—H13 | 118.1 (11) | C11—C10—H17 | 115.6 (13) |
C2—C3—C4 | 120.58 (16) | O9—C10—H18 | 104.3 (12) |
C2—C3—H14 | 119.7 (10) | C11—C10—H18 | 113.4 (12) |
C4—C3—H14 | 119.6 (10) | H17—C10—H18 | 109.7 (19) |
N12—C4—C3 | 120.63 (15) | C10—C11—H19 | 110.8 (15) |
N12—C4—C5 | 121.10 (16) | C10—C11—H20 | 110.6 (13) |
C3—C4—C5 | 118.23 (15) | H19—C11—H20 | 109 (2) |
C6—C5—C4 | 120.73 (16) | C10—C11—H21 | 112.8 (14) |
C6—C5—H15 | 122.6 (10) | H19—C11—H21 | 106 (2) |
C4—C5—H15 | 116.6 (10) | H20—C11—H21 | 106.9 (19) |
C5—C6—C1 | 121.18 (15) | C4—N12—H22 | 117.3 (13) |
C5—C6—H16 | 120.1 (10) | C4—N12—H23 | 116.8 (12) |
C1—C6—H16 | 118.7 (10) | H22—N12—H23 | 120.3 (18) |
O8—C7—O9 | 122.07 (15) | ||
C6—C1—C2—C3 | 0.8 (3) | C7—C1—C6—C5 | 179.44 (15) |
C7—C1—C2—C3 | −179.47 (15) | C6—C1—C7—O8 | 4.0 (3) |
C1—C2—C3—C4 | 0.0 (3) | C2—C1—C7—O8 | −175.79 (16) |
C2—C3—C4—N12 | −178.38 (16) | C6—C1—C7—O9 | −175.04 (14) |
C2—C3—C4—C5 | −0.7 (3) | C2—C1—C7—O9 | 5.2 (2) |
N12—C4—C5—C6 | 178.35 (15) | O8—C7—O9—C10 | 0.5 (3) |
C3—C4—C5—C6 | 0.7 (2) | C1—C7—O9—C10 | 179.58 (17) |
C4—C5—C6—C1 | 0.1 (3) | C7—O9—C10—C11 | −176.18 (18) |
C2—C1—C6—C5 | −0.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N12—H22···O8i | 0.86 (2) | 2.11 (2) | 2.956 (2) | 168.5 (18) |
N12—H23···N12ii | 0.91 (2) | 2.43 (2) | 3.3165 (19) | 165.3 (16) |
Symmetry codes: (i) x−1, y, z; (ii) −x, y−1/2, −z+1/2. |
C9H11NO2 | F(000) = 352 |
Mr = 165.19 | Dx = 1.199 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P_2n_2a | Cell parameters from 87498 reflections |
a = 8.2424 (4) Å | θ = 2.6–27.5° |
b = 5.3111 (3) Å | µ = 0.09 mm−1 |
c = 20.9044 (12) Å | T = 300 K |
V = 915.12 (9) Å3 | Block, colourless |
Z = 4 | 0.28 × 0.24 × 0.17 mm |
KappaCCD diffractometer | 1241 independent reflections |
Radiation source: fine-focus sealed tube | 1003 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.066 |
Detector resolution: 9 pixels mm-1 | θmax = 27.5°, θmin = 2.7° |
CCD scans | h = −10→10 |
Absorption correction: integration Gaussian integration (Coppens, 1970) | k = −6→6 |
Tmin = 0.958, Tmax = 0.978 | l = −27→27 |
20874 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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0568P)2 + 0.047P] where P = (Fo2 + 2Fc2)/3 |
1241 reflections | (Δ/σ)max < 0.001 |
117 parameters | Δρmax = 0.08 e Å−3 |
0 restraints | Δρmin = −0.08 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 | 0.4689 (2) | 0.4008 (4) | 0.35899 (8) | 0.0695 (5) | |
C6 | 0.4584 (3) | 0.1916 (4) | 0.31889 (9) | 0.0752 (5) | |
H16 | 0.5528 | 0.1099 | 0.3061 | 0.090* | |
C5 | 0.3117 (3) | 0.1047 (4) | 0.29808 (9) | 0.0754 (5) | |
H15 | 0.3079 | −0.0347 | 0.2712 | 0.091* | |
C4 | 0.1678 (3) | 0.2212 (4) | 0.31642 (9) | 0.0717 (5) | |
C3 | 0.1778 (3) | 0.4337 (4) | 0.35550 (10) | 0.0799 (5) | |
H14 | 0.0837 | 0.5178 | 0.3675 | 0.096* | |
C2 | 0.3256 (3) | 0.5191 (4) | 0.37624 (9) | 0.0782 (5) | |
H13 | 0.3298 | 0.6601 | 0.4026 | 0.094* | |
C7 | 0.6287 (3) | 0.4890 (4) | 0.38049 (9) | 0.0768 (5) | |
O8 | 0.75711 (19) | 0.4041 (4) | 0.36279 (8) | 0.1012 (6) | |
O9 | 0.61964 (19) | 0.6744 (3) | 0.42355 (7) | 0.0905 (5) | |
C10 | 0.7728 (3) | 0.7766 (6) | 0.44661 (13) | 0.1036 (8) | |
H17 | 0.8311 | 0.8465 | 0.4128 | 0.124* | |
H18 | 0.8353 | 0.649 | 0.4649 | 0.124* | |
C11 | 0.7352 (4) | 0.9723 (7) | 0.49486 (13) | 0.1154 (9) | |
H19 | 0.6634 | 1.0949 | 0.4765 | 0.173* | |
H20 | 0.8338 | 1.0532 | 0.5081 | 0.173* | |
H21 | 0.6841 | 0.8955 | 0.5312 | 0.173* | |
N12 | 0.0191 (2) | 0.1378 (4) | 0.29485 (10) | 0.0898 (6) | |
H23 | 0.017 (3) | −0.035 (5) | 0.2773 (11) | 0.108* | |
H22 | −0.074 (3) | 0.199 (5) | 0.3138 (12) | 0.108* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0782 (12) | 0.0682 (11) | 0.0620 (9) | 0.0017 (10) | 0.0028 (9) | 0.0014 (9) |
C6 | 0.0805 (12) | 0.0684 (11) | 0.0767 (10) | 0.0058 (11) | 0.0076 (10) | −0.0054 (10) |
C5 | 0.0880 (13) | 0.0649 (11) | 0.0734 (10) | 0.0029 (11) | 0.0039 (10) | −0.0100 (9) |
C4 | 0.0833 (12) | 0.0658 (10) | 0.0661 (9) | 0.0023 (10) | −0.0016 (9) | 0.0016 (9) |
C3 | 0.0799 (12) | 0.0742 (12) | 0.0856 (12) | 0.0122 (12) | 0.0014 (10) | −0.0126 (10) |
C2 | 0.0872 (12) | 0.0695 (11) | 0.0779 (11) | 0.0064 (12) | 0.0003 (10) | −0.0141 (10) |
C7 | 0.0832 (12) | 0.0786 (13) | 0.0686 (10) | −0.0007 (11) | 0.0006 (10) | −0.0007 (10) |
O8 | 0.0782 (9) | 0.1189 (14) | 0.1065 (12) | −0.0008 (10) | 0.0062 (8) | −0.0239 (11) |
O9 | 0.0901 (10) | 0.0908 (10) | 0.0905 (9) | −0.0025 (9) | −0.0085 (8) | −0.0189 (9) |
C10 | 0.0949 (17) | 0.111 (2) | 0.1043 (16) | −0.0133 (16) | −0.0134 (13) | −0.0155 (17) |
C11 | 0.132 (2) | 0.107 (2) | 0.1069 (17) | −0.0092 (18) | −0.0227 (16) | −0.0195 (16) |
N12 | 0.0825 (12) | 0.0827 (13) | 0.1041 (14) | −0.0012 (11) | −0.0036 (10) | −0.0173 (11) |
C1—C2 | 1.386 (3) | C7—O8 | 1.209 (3) |
C1—C6 | 1.395 (3) | C7—O9 | 1.336 (2) |
C1—C7 | 1.468 (3) | O9—C10 | 1.457 (3) |
C6—C5 | 1.365 (3) | C10—C11 | 1.481 (4) |
C6—H16 | 0.9300 | C10—H17 | 0.9320 |
C5—C4 | 1.392 (3) | C10—H18 | 0.9320 |
C5—H15 | 0.9300 | C11—H19 | 0.9600 |
C4—N12 | 1.379 (3) | C11—H20 | 0.9600 |
C4—C3 | 1.396 (3) | C11—H21 | 0.9600 |
C3—C2 | 1.370 (3) | N12—H23 | 0.99 (3) |
C3—H14 | 0.9300 | N12—H22 | 0.92 (2) |
C2—H13 | 0.9300 | ||
C2—C1—C6 | 117.67 (18) | O8—C7—C1 | 124.93 (19) |
C2—C1—C7 | 122.71 (18) | O9—C7—C1 | 113.04 (19) |
C6—C1—C7 | 119.62 (18) | C7—O9—C10 | 116.69 (19) |
C5—C6—C1 | 121.07 (19) | O9—C10—C11 | 107.8 (2) |
C5—C6—H16 | 119.5 | O9—C10—H17 | 110.2 |
C1—C6—H16 | 119.5 | C11—C10—H17 | 110.2 |
C6—C5—C4 | 121.10 (18) | O9—C10—H18 | 110.2 |
C6—C5—H15 | 119.4 | C11—C10—H18 | 110.2 |
C4—C5—H15 | 119.4 | H17—C10—H18 | 108.5 |
N12—C4—C5 | 121.63 (18) | C10—C11—H19 | 109.5 |
N12—C4—C3 | 120.27 (19) | C10—C11—H20 | 109.5 |
C5—C4—C3 | 118.05 (18) | H19—C11—H20 | 109.5 |
C2—C3—C4 | 120.36 (19) | C10—C11—H21 | 109.5 |
C2—C3—H14 | 119.8 | H19—C11—H21 | 109.5 |
C4—C3—H14 | 119.8 | H20—C11—H21 | 109.5 |
C3—C2—C1 | 121.71 (18) | C4—N12—H23 | 115.6 (16) |
C3—C2—H13 | 119.1 | C4—N12—H22 | 119.1 (16) |
C1—C2—H13 | 119.1 | H23—N12—H22 | 118 (2) |
O8—C7—O9 | 122.0 (2) | ||
C2—C1—C6—C5 | −0.8 (3) | C7—C1—C2—C3 | 179.9 (2) |
C7—C1—C6—C5 | 179.9 (2) | C2—C1—C7—O8 | −174.0 (2) |
C1—C6—C5—C4 | −0.3 (3) | C6—C1—C7—O8 | 5.2 (3) |
C6—C5—C4—N12 | 178.9 (2) | C2—C1—C7—O9 | 7.1 (3) |
C6—C5—C4—C3 | 1.5 (3) | C6—C1—C7—O9 | −173.69 (16) |
N12—C4—C3—C2 | −179.1 (2) | O8—C7—O9—C10 | 2.2 (3) |
C5—C4—C3—C2 | −1.7 (3) | C1—C7—O9—C10 | −178.9 (2) |
C4—C3—C2—C1 | 0.6 (3) | C7—O9—C10—C11 | −178.3 (2) |
C6—C1—C2—C3 | 0.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N12—H22···O8i | 0.92 (2) | 2.04 (3) | 2.946 (3) | 166 (2) |
N12—H23···N12ii | 0.99 (3) | 2.32 (3) | 3.266 (2) | 160 (2) |
Symmetry codes: (i) x−1, y, z; (ii) −x, y−1/2, −z+1/2. |
C9H11NO2 | F(000) = 704 |
Mr = 165.19 | Dx = 1.247 Mg m−3 |
Monoclinic, P1121 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2c | Cell parameters from 156810 reflections |
a = 8.1883 (4) Å | θ = 2.6–27.5° |
b = 10.6394 (5) Å | µ = 0.09 mm−1 |
c = 20.4761 (10) Å | T = 300 K |
β = 90° | Block, colourless |
V = 1760.05 (15) Å3 | 0.28 × 0.24 × 0.17 mm |
Z = 8 |
KappaCCD diffractometer | 7859 independent reflections |
Radiation source: fine-focus sealed tube | 6013 reflections with I > 3 σ(I) |
Graphite monochromator | Rint = 0.063 |
Detector resolution: 9 pixels mm-1 | θmax = 27.6°, θmin = 2.7° |
CCD scans | h = −10→10 |
Absorption correction: integration Gaussian integration (Coppens, 1970) | k = −13→13 |
Tmin = 0.952, Tmax = 0.974 | l = −26→26 |
24960 measured reflections |
Refinement on F | Primary atom site location: packing arguments |
Least-squares matrix: full | Secondary atom site location: packing arguments |
R[F2 > 2σ(F2)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 2.10 | w = 1/[σ2(F) + (0.03F)2] |
6013 reflections | (Δ/σ)max = 0.01 |
143 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.11 e Å−3 |
Experimental. The twinning in Form III was ignored in the data processing, reflection intensities being obtained using only reflection positions h for the major twin component. |
Refinement. The final twin ratio was 0.523 (2):0.477. The twinning was included in the model for observed intensities as Ycalc(h) = a I(h) + (1 - a) K(|h-h'|) I(h') where K(|h-h'|) is an empirical function allowing for overlap with the nearest twin related reflection h'. K(|h-h'|) is 0.5 if p = |h-h'| is equal to a refinable parameter p1, 1.0 if less than a refinable parameter p2, 0.0 if greater than 2 p1 - p2 and 0.5 - 0.5 sin[Pi (p - p1)/2(p1 - p2)] for p in the range p2 to 2 p1 - p2. The nearest twin related reflection to h,k,l has h' = h, l' = - l and k' the nearest integer to -k -0.42309 h. Final parameter values were p1 = 0.139 (3) b* and p2 = 0.0. To demonstrate the adequacy of the twin overlap model the reflection data considered observed were separated into 8 sets, corresponding to p = 0, 0 < p/b* = 0.1, 0.1 < p/b* = 0.2 and p/b* > 0.2 for k even (1 to 4) and k odd (5 to 8) respectively. For the 216, 299, 845, 1578, 210, 299, 869, 1697 reflections in each set the final values for R(F) were 0.063, 0.041, 0.082, 0.072, 0.059, 0.042, 0.080, 0.057. Rigid body TLX parameterization was used to describe and refine the atomic displacement parameters of every atom in a molecule. |
x | y | z | Uiso*/Ueq | ||
C11 | 0.5566 (2) | 0.32209 (15) | 0.36344 (6) | 0.0272 (4) | |
C12 | 0.5277 (2) | 0.21927 (19) | 0.32048 (9) | 0.0311 (4) | |
C13 | 0.3693 (2) | 0.17263 (17) | 0.29933 (9) | 0.0304 (4) | |
C14 | 0.2346 (2) | 0.22807 (15) | 0.32077 (8) | 0.0287 (4) | |
C15 | 0.2645 (2) | 0.33153 (18) | 0.36400 (10) | 0.0304 (4) | |
C16 | 0.4233 (2) | 0.37753 (17) | 0.38490 (9) | 0.0283 (4) | |
C17 | 0.7276 (3) | 0.3689 (2) | 0.38480 (10) | 0.0312 (4) | |
O18 | 0.8487 (3) | 0.3239 (3) | 0.36865 (13) | 0.0401 (5) | |
O19 | 0.7374 (3) | 0.4651 (2) | 0.42774 (12) | 0.0325 (4) | |
C110 | 0.9029 (4) | 0.5163 (4) | 0.45196 (19) | 0.0394 (6) | |
C111 | 0.8810 (5) | 0.6131 (4) | 0.5028 (2) | 0.0470 (11) | |
N112 | 0.0767 (2) | 0.1822 (2) | 0.29996 (11) | 0.0337 (4) | |
C21 | 0.7047 (2) | 0.56163 (15) | 0.13936 (7) | 0.0285 (4) | |
C22 | 0.6906 (2) | 0.45818 (19) | 0.18190 (9) | 0.0313 (4) | |
C23 | 0.8298 (2) | 0.41356 (17) | 0.20404 (9) | 0.0298 (5) | |
C24 | 0.9880 (2) | 0.47171 (15) | 0.18405 (8) | 0.0291 (5) | |
C25 | 1.0015 (2) | 0.57579 (18) | 0.14123 (10) | 0.0309 (5) | |
C26 | 0.8616 (2) | 0.61977 (17) | 0.11934 (9) | 0.0287 (5) | |
C27 | 0.5530 (3) | 0.6062 (2) | 0.11691 (10) | 0.0329 (4) | |
O28 | 0.4131 (3) | 0.5538 (2) | 0.13033 (14) | 0.0420 (7) | |
O29 | 0.5813 (3) | 0.7059 (2) | 0.07689 (12) | 0.0328 (4) | |
C210 | 0.4357 (4) | 0.7532 (4) | 0.0525 (2) | 0.0395 (6) | |
C211 | 0.4938 (5) | 0.8655 (4) | 0.0093 (2) | 0.0425 (9) | |
N212 | 1.1271 (2) | 0.4279 (2) | 0.20586 (11) | 0.0336 (6) | |
C31 | 0.7033 (2) | 0.81687 (16) | 0.35695 (6) | 0.0281 (5) | |
C32 | 0.6712 (2) | 0.70534 (19) | 0.32019 (9) | 0.0308 (5) | |
C33 | 0.5130 (2) | 0.65943 (17) | 0.29862 (9) | 0.0301 (5) | |
C34 | 0.3817 (2) | 0.72441 (15) | 0.31339 (8) | 0.0301 (4) | |
C35 | 0.4146 (2) | 0.83662 (18) | 0.35040 (10) | 0.0338 (4) | |
C36 | 0.5733 (2) | 0.88181 (17) | 0.37176 (9) | 0.0310 (4) | |
C37 | 0.8740 (3) | 0.8625 (2) | 0.37898 (10) | 0.0310 (5) | |
O38 | 0.9935 (3) | 0.8136 (2) | 0.36615 (13) | 0.0386 (6) | |
O39 | 0.8832 (3) | 0.9591 (2) | 0.42229 (12) | 0.0324 (4) | |
C310 | 1.0443 (4) | 1.0066 (3) | 0.44995 (18) | 0.0371 (5) | |
C311 | 1.0274 (5) | 1.1221 (4) | 0.4900 (2) | 0.0448 (6) | |
N312 | 0.2239 (2) | 0.6794 (2) | 0.29212 (11) | 0.0346 (5) | |
C41 | 0.8234 (2) | 0.06483 (16) | 0.14551 (6) | 0.0303 (4) | |
C42 | 0.8084 (2) | −0.04434 (19) | 0.18410 (9) | 0.0332 (4) | |
C43 | 0.9458 (2) | −0.09817 (17) | 0.19974 (9) | 0.0323 (4) | |
C44 | 1.1031 (2) | −0.04379 (16) | 0.17699 (8) | 0.0320 (4) | |
C45 | 1.1175 (2) | 0.06608 (19) | 0.13816 (10) | 0.0344 (5) | |
C46 | 0.9794 (2) | 0.11926 (18) | 0.12278 (9) | 0.0318 (5) | |
C47 | 0.6736 (3) | 0.1192 (2) | 0.12998 (11) | 0.0341 (4) | |
O48 | 0.5359 (3) | 0.0809 (3) | 0.15084 (14) | 0.0427 (5) | |
O49 | 0.6984 (3) | 0.1995 (2) | 0.07735 (12) | 0.0351 (5) | |
C410 | 0.5552 (5) | 0.2492 (4) | 0.0535 (2) | 0.0414 (7) | |
C411 | 0.6131 (5) | 0.3457 (4) | 0.0019 (2) | 0.0474 (9) | |
N412 | 1.2404 (2) | −0.0968 (2) | 0.19233 (12) | 0.0370 (5) | |
H1C12 | 0.62256 | 0.17886 | 0.30482 | 0.040 | |
H1C13 | 0.35037 | 0.09879 | 0.26850 | 0.037 | |
H1C15 | 0.17003 | 0.37228 | 0.37982 | 0.039 | |
H1C16 | 0.44288 | 0.45135 | 0.41572 | 0.033 | |
H1C110 | 0.97365 | 0.55727 | 0.41552 | 0.045 | |
H2C110 | 0.95558 | 0.44670 | 0.47158 | 0.042 | |
H1C111 | 0.99152 | 0.65103 | 0.52088 | 0.053 | |
H2C111 | 0.82744 | 0.68183 | 0.48271 | 0.052 | |
H3C111 | 0.80937 | 0.57126 | 0.53877 | 0.049 | |
H1N112 | 0.05655 | 0.10843 | 0.26913 | 0.036 | |
H2N112 | −0.01816 | 0.22267 | 0.31563 | 0.040 | |
H1C22 | 0.57853 | 0.41585 | 0.19654 | 0.039 | |
H1C23 | 0.81776 | 0.33923 | 0.23456 | 0.034 | |
H1C25 | 1.11328 | 0.61846 | 0.12644 | 0.038 | |
H1C26 | 0.87297 | 0.69406 | 0.08882 | 0.032 | |
H1C210 | 0.37064 | 0.77985 | 0.08991 | 0.046 | |
H2C210 | 0.36486 | 0.68499 | 0.02696 | 0.042 | |
H1C211 | 0.39592 | 0.89992 | −0.00816 | 0.048 | |
H2C211 | 0.56501 | 0.93313 | 0.03509 | 0.046 | |
H3C211 | 0.55924 | 0.83828 | −0.02787 | 0.042 | |
H1N212 | 1.11632 | 0.35362 | 0.23638 | 0.034 | |
H2N212 | 1.23914 | 0.47024 | 0.19121 | 0.040 | |
H1C32 | 0.76374 | 0.65808 | 0.30932 | 0.038 | |
H1C33 | 0.49181 | 0.57927 | 0.27229 | 0.035 | |
H1C35 | 0.32258 | 0.88423 | 0.36140 | 0.044 | |
H1C36 | 0.59513 | 0.96193 | 0.39811 | 0.037 | |
H1C310 | 1.12686 | 1.03034 | 0.41423 | 0.039 | |
H2C310 | 1.08117 | 0.93998 | 0.47827 | 0.041 | |
H1C311 | 1.13687 | 1.15742 | 0.50989 | 0.049 | |
H2C311 | 0.98994 | 1.18805 | 0.46140 | 0.048 | |
H3C311 | 0.94424 | 1.09769 | 0.52545 | 0.050 | |
H1N312 | 0.20149 | 0.59929 | 0.26576 | 0.035 | |
H2N312 | 0.13141 | 0.72665 | 0.30300 | 0.042 | |
H1C42 | 0.69697 | −0.08407 | 0.20064 | 0.041 | |
H1C43 | 0.93313 | −0.17652 | 0.22748 | 0.037 | |
H1C45 | 1.22863 | 0.10619 | 0.12150 | 0.043 | |
H1C46 | 0.99139 | 0.19760 | 0.09505 | 0.036 | |
H1C410 | 0.50238 | 0.29026 | 0.09009 | 0.044 | |
H2C410 | 0.47321 | 0.17861 | 0.03461 | 0.047 | |
H1C411 | 0.51652 | 0.38178 | −0.01553 | 0.053 | |
H2C411 | 0.69542 | 0.41568 | 0.02110 | 0.049 | |
H3C411 | 0.66625 | 0.30402 | −0.03439 | 0.052 | |
H1N412 | 1.22896 | −0.17510 | 0.22004 | 0.038 | |
H2N412 | 1.35177 | −0.05700 | 0.17578 | 0.044 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.0267 (5) | 0.0276 (6) | 0.0272 (7) | 0.0047 (4) | 0.0003 (4) | −0.0009 (5) |
C12 | 0.0285 (4) | 0.0320 (6) | 0.0333 (7) | 0.0070 (4) | −0.0009 (5) | −0.0062 (5) |
C13 | 0.0296 (5) | 0.0297 (7) | 0.0322 (7) | 0.0055 (4) | −0.0015 (5) | −0.0048 (6) |
C14 | 0.0273 (5) | 0.0295 (6) | 0.0289 (6) | 0.0038 (4) | −0.0003 (4) | −0.0013 (5) |
C15 | 0.0271 (5) | 0.0328 (6) | 0.0318 (6) | 0.0062 (4) | −0.0001 (5) | −0.0047 (5) |
C16 | 0.0277 (4) | 0.0286 (7) | 0.0289 (7) | 0.0054 (4) | −0.0001 (4) | −0.0028 (5) |
C17 | 0.0271 (4) | 0.0341 (6) | 0.0323 (6) | 0.0045 (4) | −0.0008 (4) | −0.0033 (4) |
O18 | 0.0274 (5) | 0.0485 (11) | 0.0451 (12) | 0.0081 (4) | −0.0025 (5) | −0.0124 (8) |
O19 | 0.0299 (5) | 0.0333 (7) | 0.0334 (7) | 0.0027 (4) | −0.0025 (4) | −0.0037 (5) |
C110 | 0.0320 (5) | 0.0426 (10) | 0.0417 (10) | 0.0006 (6) | −0.0055 (6) | −0.0068 (8) |
C111 | 0.0403 (10) | 0.0479 (15) | 0.0507 (15) | 0.0009 (9) | −0.0101 (10) | −0.0157 (12) |
N112 | 0.0282 (5) | 0.0371 (6) | 0.0350 (7) | 0.0027 (4) | −0.0019 (5) | −0.0039 (6) |
C21 | 0.0253 (6) | 0.0294 (6) | 0.0297 (6) | 0.0016 (4) | 0.0010 (5) | 0.0005 (5) |
C22 | 0.0258 (7) | 0.0334 (6) | 0.0335 (6) | 0.0011 (5) | 0.0023 (5) | 0.0046 (6) |
C23 | 0.0273 (6) | 0.0302 (7) | 0.0307 (7) | 0.0012 (5) | 0.0009 (5) | 0.0023 (6) |
C24 | 0.0259 (5) | 0.0295 (6) | 0.0308 (6) | 0.0013 (4) | −0.0005 (5) | 0.0004 (5) |
C25 | 0.0250 (5) | 0.0313 (5) | 0.0348 (8) | −0.0003 (5) | −0.0000 (6) | 0.0032 (5) |
C26 | 0.0259 (5) | 0.0280 (6) | 0.0308 (7) | 0.0001 (4) | 0.0001 (5) | 0.0010 (5) |
C27 | 0.0266 (6) | 0.0360 (5) | 0.0358 (6) | 0.0042 (4) | 0.0009 (4) | 0.0032 (5) |
O28 | 0.0258 (8) | 0.0496 (11) | 0.0503 (12) | 0.0051 (6) | 0.0023 (4) | 0.0127 (9) |
O29 | 0.0306 (6) | 0.0331 (6) | 0.0348 (7) | 0.0052 (4) | −0.0016 (5) | 0.0012 (5) |
C210 | 0.0348 (8) | 0.0417 (8) | 0.0432 (11) | 0.0102 (7) | −0.0035 (7) | 0.0038 (7) |
C211 | 0.0441 (12) | 0.0394 (10) | 0.0456 (15) | 0.0111 (9) | −0.0071 (10) | 0.0048 (9) |
N212 | 0.0278 (5) | 0.0352 (6) | 0.0373 (7) | 0.0034 (5) | −0.0021 (6) | 0.0027 (5) |
C31 | 0.0289 (5) | 0.0281 (7) | 0.0271 (8) | 0.0042 (4) | 0.0014 (5) | −0.0002 (5) |
C32 | 0.0295 (5) | 0.0311 (7) | 0.0319 (8) | 0.0051 (5) | 0.0015 (5) | −0.0042 (5) |
C33 | 0.0304 (5) | 0.0302 (7) | 0.0293 (7) | 0.0041 (4) | 0.0010 (5) | −0.0028 (5) |
C34 | 0.0296 (5) | 0.0297 (6) | 0.0308 (7) | 0.0045 (4) | −0.0005 (5) | −0.0007 (5) |
C35 | 0.0301 (5) | 0.0314 (7) | 0.0403 (10) | 0.0068 (4) | −0.0016 (5) | −0.0053 (7) |
C36 | 0.0303 (5) | 0.0290 (7) | 0.0340 (9) | 0.0056 (4) | −0.0002 (5) | −0.0033 (6) |
C37 | 0.0293 (5) | 0.0314 (7) | 0.0318 (7) | 0.0038 (4) | 0.0004 (5) | −0.0016 (4) |
O38 | 0.0290 (6) | 0.0398 (11) | 0.0469 (12) | 0.0057 (5) | −0.0008 (5) | −0.0089 (7) |
O39 | 0.0321 (5) | 0.0318 (6) | 0.0325 (7) | 0.0026 (4) | −0.0011 (5) | −0.0024 (5) |
C310 | 0.0344 (6) | 0.0370 (8) | 0.0384 (10) | 0.0009 (5) | −0.0041 (6) | −0.0033 (7) |
C311 | 0.0413 (10) | 0.0431 (11) | 0.0476 (16) | −0.0005 (8) | −0.0058 (10) | −0.0124 (11) |
N312 | 0.0307 (5) | 0.0341 (7) | 0.0387 (9) | 0.0043 (4) | −0.0032 (6) | −0.0024 (6) |
C41 | 0.0317 (6) | 0.0299 (6) | 0.0278 (8) | 0.0005 (4) | 0.0000 (5) | −0.0005 (5) |
C42 | 0.0322 (6) | 0.0327 (6) | 0.0329 (8) | 0.0004 (4) | 0.0013 (5) | 0.0034 (6) |
C43 | 0.0335 (5) | 0.0310 (6) | 0.0307 (9) | 0.0006 (4) | −0.0002 (5) | 0.0017 (6) |
C44 | 0.0324 (6) | 0.0315 (5) | 0.0308 (7) | 0.0014 (4) | −0.0004 (5) | 0.0002 (5) |
C45 | 0.0318 (6) | 0.0345 (5) | 0.0355 (7) | 0.0010 (4) | 0.0017 (5) | 0.0042 (5) |
C46 | 0.0323 (5) | 0.0312 (6) | 0.0303 (8) | 0.0003 (4) | 0.0007 (5) | 0.0018 (5) |
C47 | 0.0327 (5) | 0.0338 (5) | 0.0348 (7) | 0.0022 (4) | −0.0004 (4) | 0.0016 (5) |
O48 | 0.0328 (6) | 0.0441 (11) | 0.0506 (12) | 0.0046 (5) | 0.0029 (5) | 0.0099 (8) |
O49 | 0.0365 (6) | 0.0337 (6) | 0.0342 (8) | 0.0028 (4) | −0.0033 (5) | 0.0014 (5) |
C410 | 0.0402 (8) | 0.0387 (9) | 0.0448 (11) | 0.0054 (7) | −0.0074 (7) | 0.0034 (8) |
C411 | 0.0504 (14) | 0.0451 (14) | 0.0472 (16) | 0.0090 (11) | −0.0081 (11) | 0.0094 (11) |
N412 | 0.0342 (6) | 0.0364 (6) | 0.0398 (8) | 0.0038 (5) | −0.0013 (5) | 0.0026 (5) |
H1C12 | 0.031 | 0.044 | 0.046 | 0.011 | −0.003 | −0.017 |
H1C13 | 0.034 | 0.036 | 0.042 | 0.007 | −0.004 | −0.012 |
H1C15 | 0.029 | 0.045 | 0.044 | 0.010 | −0.002 | −0.014 |
H1C16 | 0.031 | 0.034 | 0.036 | 0.007 | −0.002 | −0.009 |
H1C110 | 0.033 | 0.049 | 0.047 | −0.005 | −0.004 | −0.005 |
H2C110 | 0.033 | 0.049 | 0.045 | 0.005 | −0.009 | −0.008 |
H1C111 | 0.043 | 0.055 | 0.058 | −0.002 | −0.013 | −0.018 |
H2C111 | 0.047 | 0.042 | 0.065 | 0.001 | −0.014 | −0.018 |
H3C111 | 0.042 | 0.059 | 0.044 | 0.003 | −0.009 | −0.019 |
H1N112 | 0.031 | 0.037 | 0.038 | 0.001 | −0.004 | −0.005 |
H2N112 | 0.027 | 0.048 | 0.043 | 0.005 | −0.002 | −0.010 |
H1C22 | 0.027 | 0.044 | 0.045 | 0.001 | 0.004 | 0.013 |
H1C23 | 0.031 | 0.034 | 0.036 | 0.002 | 0.001 | 0.007 |
H1C25 | 0.025 | 0.040 | 0.047 | −0.001 | 0.000 | 0.011 |
H1C26 | 0.028 | 0.030 | 0.036 | −0.000 | −0.000 | 0.004 |
H1C210 | 0.040 | 0.053 | 0.048 | 0.019 | 0.000 | 0.005 |
H2C210 | 0.033 | 0.045 | 0.049 | 0.007 | −0.008 | 0.006 |
H1C211 | 0.049 | 0.046 | 0.052 | 0.016 | −0.010 | 0.006 |
H2C211 | 0.051 | 0.036 | 0.051 | 0.012 | −0.010 | 0.004 |
H3C211 | 0.045 | 0.041 | 0.042 | 0.009 | −0.006 | 0.008 |
H1N212 | 0.032 | 0.035 | 0.037 | 0.005 | −0.003 | 0.002 |
H2N212 | 0.027 | 0.044 | 0.049 | 0.004 | −0.002 | 0.009 |
H1C32 | 0.031 | 0.038 | 0.047 | 0.007 | 0.000 | −0.013 |
H1C33 | 0.033 | 0.035 | 0.037 | 0.004 | 0.000 | −0.009 |
H1C35 | 0.032 | 0.039 | 0.061 | 0.010 | −0.005 | −0.015 |
H1C36 | 0.033 | 0.032 | 0.045 | 0.007 | −0.002 | −0.010 |
H1C310 | 0.033 | 0.040 | 0.043 | −0.001 | −0.002 | −0.003 |
H2C310 | 0.038 | 0.042 | 0.042 | 0.001 | −0.010 | −0.001 |
H1C311 | 0.044 | 0.048 | 0.052 | −0.003 | −0.009 | −0.013 |
H2C311 | 0.044 | 0.037 | 0.061 | 0.001 | −0.009 | −0.013 |
H3C311 | 0.045 | 0.056 | 0.046 | −0.002 | −0.003 | −0.020 |
H1N312 | 0.033 | 0.035 | 0.036 | 0.002 | −0.003 | −0.002 |
H2N312 | 0.031 | 0.040 | 0.056 | 0.007 | −0.006 | −0.008 |
H1C42 | 0.033 | 0.041 | 0.047 | 0.001 | 0.004 | 0.012 |
H1C43 | 0.037 | 0.034 | 0.038 | 0.001 | −0.000 | 0.007 |
H1C45 | 0.032 | 0.044 | 0.051 | 0.002 | 0.005 | 0.014 |
H1C46 | 0.035 | 0.035 | 0.038 | 0.001 | 0.001 | 0.007 |
H1C410 | 0.040 | 0.042 | 0.051 | 0.009 | −0.004 | 0.004 |
H2C410 | 0.043 | 0.042 | 0.054 | 0.005 | −0.015 | 0.003 |
H1C411 | 0.055 | 0.049 | 0.056 | 0.012 | −0.013 | 0.011 |
H2C411 | 0.049 | 0.041 | 0.055 | 0.006 | −0.006 | 0.013 |
H3C411 | 0.061 | 0.056 | 0.042 | 0.015 | −0.007 | 0.012 |
H1N412 | 0.037 | 0.036 | 0.040 | 0.005 | −0.004 | 0.002 |
H2N412 | 0.034 | 0.045 | 0.054 | 0.006 | 0.001 | 0.009 |
C11—C12 | 1.394 (1) | O49—C410 | 1.447 (4) |
C11—C16 | 1.394 (1) | C410—C411 | 1.496 (5) |
C11—C17 | 1.474 (2) | C12—H1C12 | 1.000 |
C12—C13 | 1.381 (2) | C13—H1C13 | 1.000 |
C13—C14 | 1.403 (1) | C15—H1C15 | 1.000 |
C14—C15 | 1.403 (1) | C16—H1C16 | 1.000 |
C14—N112 | 1.373 (2) | C110—H1C110 | 1.000 |
C15—C16 | 1.381 (2) | C110—H2C110 | 1.000 |
C17—O18 | 1.215 (3) | C111—H1C111 | 1.000 |
C17—O19 | 1.342 (3) | C111—H2C111 | 1.000 |
O19—C110 | 1.463 (4) | C111—H3C111 | 1.000 |
C110—C111 | 1.495 (6) | N112—H1N112 | 1.000 |
C21—C22 | 1.394 (1) | N112—H2N112 | 1.000 |
C21—C26 | 1.394 (1) | C22—H1C22 | 1.000 |
C21—C27 | 1.474 (2) | C23—H1C23 | 1.000 |
C22—C23 | 1.381 (2) | C25—H1C25 | 1.000 |
C23—C24 | 1.403 (1) | C26—H1C26 | 1.000 |
C24—C25 | 1.403 (1) | C210—H1C210 | 1.000 |
C24—N212 | 1.373 (2) | C210—H2C210 | 1.000 |
C25—C26 | 1.381 (2) | C211—H1C211 | 1.000 |
C27—O28 | 1.221 (3) | C211—H2C211 | 1.000 |
C27—O29 | 1.330 (3) | C211—H3C211 | 1.000 |
O29—C210 | 1.455 (4) | N212—H1N212 | 1.000 |
C210—C211 | 1.501 (5) | N212—H2N212 | 1.000 |
C31—C32 | 1.394 (1) | C32—H1C32 | 1.000 |
C31—C36 | 1.394 (1) | C33—H1C33 | 1.000 |
C31—C37 | 1.474 (2) | C35—H1C35 | 1.000 |
C32—C33 | 1.381 (2) | C36—H1C36 | 1.000 |
C33—C34 | 1.403 (1) | C310—H1C310 | 1.000 |
C34—C35 | 1.403 (1) | C310—H2C310 | 1.000 |
C34—N312 | 1.373 (2) | C311—H1C311 | 1.000 |
C35—C36 | 1.381 (2) | C311—H2C311 | 1.000 |
C37—O38 | 1.210 (3) | C311—H3C311 | 1.000 |
C37—O39 | 1.350 (3) | N312—H1N312 | 1.000 |
O39—C310 | 1.449 (4) | N312—H2N312 | 1.000 |
C310—C311 | 1.502 (5) | C42—H1C42 | 1.000 |
C41—C42 | 1.394 (1) | C43—H1C43 | 1.000 |
C41—C46 | 1.394 (1) | C45—H1C45 | 1.000 |
C41—C47 | 1.474 (2) | C46—H1C46 | 1.000 |
C42—C43 | 1.381 (2) | C410—H1C410 | 1.000 |
C43—C44 | 1.403 (1) | C410—H2C410 | 1.000 |
C44—C45 | 1.403 (1) | C411—H1C411 | 1.000 |
C44—N412 | 1.373 (2) | C411—H2C411 | 1.000 |
C45—C46 | 1.381 (2) | C411—H3C411 | 1.000 |
C47—O48 | 1.212 (3) | N412—H1N412 | 1.000 |
C47—O49 | 1.369 (3) | N412—H2N412 | 1.000 |
C11···C211i | 3.578 (4) | C22···C410 | 3.504 (4) |
C13···O48 | 3.535 (3) | C23···C47 | 3.527 (3) |
C14···N212ii | 3.382 (3) | C23···O49 | 3.504 (3) |
C15···O18ii | 3.393 (3) | C24···N312iii | 3.481 (2) |
C16···C33 | 3.455 (3) | C25···O28iii | 3.423 (3) |
O18···N112iii | 2.941 (3) | C26···C43v | 3.394 (3) |
O18···C23 | 3.513 (3) | O28···N212ii | 2.941 (3) |
O19···C210i | 3.586 (4) | O28···N312 | 3.979 (4) |
O19···C32 | 3.483 (3) | N212···N312iii | 3.196 (3) |
C110···O38 | 3.588 (5) | C34···N412vi | 3.438 (3) |
C111···O38 | 3.547 (5) | C35···O38ii | 3.432 (3) |
N112···C44ii | 3.513 (3) | O38···N312iii | 2.962 (3) |
N112···N212ii | 3.219 (3) | O38···C43v | 3.573 (3) |
N112···O39iv | 3.633 (3) | N312···N412vi | 3.124 (3) |
N112···C310iv | 3.582 (4) | C45···O48iii | 3.414 (3) |
N112···C45ii | 3.571 (3) | O48···N412ii | 2.943 (3) |
C22···O49 | 3.496 (3) | ||
C12—C11—C16 | 119.1 (1) | C110—C111—H2C111 | 109.5 |
C12—C11—C17 | 118.9 (1) | C110—C111—H3C111 | 109.5 |
C16—C11—C17 | 122.0 (1) | H1C111—C111—H2C111 | 109.5 |
C11—C12—C13 | 120.6 (1) | H1C111—C111—H3C111 | 109.5 |
C12—C13—C14 | 120.5 (1) | H2C111—C111—H3C111 | 109.5 |
C13—C14—C15 | 118.6 (1) | C14—N112—H1N112 | 120.0 |
C13—C14—N112 | 120.8 (1) | C14—N112—H2N112 | 120.0 |
C15—C14—N112 | 120.5 (1) | H1N112—N112—H2N112 | 120.0 |
C14—C15—C16 | 120.5 (1) | C21—C22—H1C22 | 119.7 |
C11—C16—C15 | 120.6 (1) | C23—C22—H1C22 | 119.7 |
C11—C17—O18 | 125.3 (2) | C22—C23—H1C23 | 119.8 |
C11—C17—O19 | 112.8 (2) | C24—C23—H1C23 | 119.8 |
O18—C17—O19 | 121.8 (2) | C24—C25—H1C25 | 119.8 |
C17—O19—C110 | 116.3 (2) | C26—C25—H1C25 | 119.8 |
O19—C110—C111 | 106.6 (3) | C21—C26—H1C26 | 119.7 |
C22—C21—C26 | 119.1 (1) | C25—C26—H1C26 | 119.7 |
C22—C21—C27 | 118.9 (1) | O29—C210—H1C210 | 109.9 |
C26—C21—C27 | 122.0 (1) | O29—C210—H2C210 | 109.9 |
C21—C22—C23 | 120.6 (1) | C211—C210—H1C210 | 109.9 |
C22—C23—C24 | 120.5 (1) | C211—C210—H2C210 | 109.9 |
C23—C24—C25 | 118.6 (1) | H1C210—C210—H2C210 | 109.5 |
C23—C24—N212 | 120.8 (1) | C210—C211—H1C211 | 109.5 |
C25—C24—N212 | 120.5 (1) | C210—C211—H2C211 | 109.5 |
C24—C25—C26 | 120.5 (1) | C210—C211—H3C211 | 109.5 |
C21—C26—C25 | 120.6 (1) | H1C211—C211—H2C211 | 109.5 |
C21—C27—O28 | 124.1 (2) | H1C211—C211—H3C211 | 109.5 |
C21—C27—O29 | 113.7 (2) | H2C211—C211—H3C211 | 109.5 |
O28—C27—O29 | 122.1 (2) | C24—N212—H1N212 | 120.0 |
C27—O29—C210 | 116.1 (2) | C24—N212—H2N212 | 120.0 |
O29—C210—C211 | 107.8 (3) | H1N212—N212—H2N212 | 120.0 |
C32—C31—C36 | 119.1 (1) | C31—C32—H1C32 | 119.7 |
C32—C31—C37 | 118.9 (1) | C33—C32—H1C32 | 119.7 |
C36—C31—C37 | 122.0 (1) | C32—C33—H1C33 | 119.8 |
C31—C32—C33 | 120.6 (1) | C34—C33—H1C33 | 119.8 |
C32—C33—C34 | 120.5 (1) | C34—C35—H1C35 | 119.8 |
C33—C34—C35 | 118.6 (1) | C36—C35—H1C35 | 119.8 |
C33—C34—N312 | 120.8 (1) | C31—C36—H1C36 | 119.7 |
C35—C34—N312 | 120.5 (1) | C35—C36—H1C36 | 119.7 |
C34—C35—C36 | 120.5 (1) | O39—C310—H1C310 | 110.0 |
C31—C36—C35 | 120.6 (1) | O39—C310—H2C310 | 110.0 |
C31—C37—O38 | 125.6 (2) | C311—C310—H1C310 | 110.0 |
C31—C37—O39 | 112.6 (2) | C311—C310—H2C310 | 110.0 |
O38—C37—O39 | 121.5 (2) | H1C310—C310—H2C310 | 109.5 |
C37—O39—C310 | 117.2 (2) | C310—C311—H1C311 | 109.5 |
O39—C310—C311 | 107.4 (3) | C310—C311—H2C311 | 109.5 |
C42—C41—C46 | 119.1 (1) | C310—C311—H3C311 | 109.5 |
C42—C41—C47 | 118.9 (1) | H1C311—C311—H2C311 | 109.5 |
C46—C41—C47 | 122.0 (1) | H1C311—C311—H3C311 | 109.5 |
C41—C42—C43 | 120.6 (1) | H2C311—C311—H3C311 | 109.5 |
C42—C43—C44 | 120.5 (1) | C34—N312—H1N312 | 120.0 |
C43—C44—C45 | 118.6 (1) | C34—N312—H2N312 | 120.0 |
C43—C44—N412 | 120.8 (1) | H1N312—N312—H2N312 | 120.0 |
C45—C44—N412 | 120.5 (1) | C41—C42—H1C42 | 119.7 |
C44—C45—C46 | 120.5 (1) | C43—C42—H1C42 | 119.7 |
C41—C46—C45 | 120.6 (1) | C42—C43—H1C43 | 119.8 |
C41—C47—O48 | 125.4 (2) | C44—C43—H1C43 | 119.8 |
C41—C47—O49 | 111.5 (2) | C44—C45—H1C45 | 119.8 |
O48—C47—O49 | 121.5 (2) | C46—C45—H1C45 | 119.8 |
C47—O49—C410 | 116.5 (2) | C41—C46—H1C46 | 119.7 |
O49—C410—C411 | 107.7 (3) | C45—C46—H1C46 | 119.7 |
C11—C12—H1C12 | 119.7 | O49—C410—H1C410 | 109.9 |
C13—C12—H1C12 | 119.7 | O49—C410—H2C410 | 109.9 |
C12—C13—H1C13 | 119.8 | C411—C410—H1C410 | 109.9 |
C14—C13—H1C13 | 119.8 | C411—C410—H2C410 | 109.9 |
C14—C15—H1C15 | 119.8 | H1C410—C410—H2C410 | 109.5 |
C16—C15—H1C15 | 119.8 | C410—C411—H1C411 | 109.5 |
C11—C16—H1C16 | 119.7 | C410—C411—H2C411 | 109.5 |
C15—C16—H1C16 | 119.7 | C410—C411—H3C411 | 109.5 |
O19—C110—H1C110 | 110.2 | H1C411—C411—H2C411 | 109.5 |
O19—C110—H2C110 | 110.2 | H1C411—C411—H3C411 | 109.5 |
C111—C110—H1C110 | 110.2 | H2C411—C411—H3C411 | 109.5 |
C111—C110—H2C110 | 110.2 | C44—N412—H1N412 | 120.0 |
H1C110—C110—H2C110 | 109.5 | C44—N412—H2N412 | 120.0 |
C110—C111—H1C111 | 109.5 | H1N412—N412—H2N412 | 120.0 |
C16—C11—C12—C13 | 0.0 | C36—C31—C32—C33 | −0.0 |
C17—C11—C12—C13 | 180.0 | C37—C31—C32—C33 | 180.0 |
C12—C11—C16—C15 | −0.0 | C32—C31—C36—C35 | −0.0 |
C17—C11—C16—C15 | −180.0 | C37—C31—C36—C35 | −180.0 |
C12—C11—C17—O18 | −1.0 (2) | C32—C31—C37—O38 | 2.6 (2) |
C12—C11—C17—O19 | −177.8 (2) | C32—C31—C37—O39 | −170.2 (2) |
C16—C11—C17—O18 | 179.0 (2) | C36—C31—C37—O38 | −177.4 (2) |
C16—C11—C17—O19 | 2.2 (2) | C36—C31—C37—O39 | 9.8 (2) |
C11—C12—C13—C14 | −0.0 | C31—C32—C33—C34 | −0.0 |
C12—C13—C14—C15 | 0.0 | C32—C33—C34—C35 | 0.0 |
C12—C13—C14—N112 | 180.0 | C32—C33—C34—N312 | 180.0 |
C13—C14—C15—C16 | −0.0 | C33—C34—C35—C36 | −0.0 |
N112—C14—C15—C16 | −180.0 | N312—C34—C35—C36 | −180.0 |
C14—C15—C16—C11 | 0.0 | C34—C35—C36—C31 | 0.0 |
C11—C17—O19—C110 | 179.4 (2) | C31—C37—O39—C310 | 176.7 (2) |
O18—C17—O19—C110 | 2.5 (4) | O38—C37—O39—C310 | 3.5 (4) |
C17—O19—C110—C111 | −175.1 (3) | C37—O39—C310—C311 | 173.5 (3) |
C26—C21—C22—C23 | −0.0 | C46—C41—C42—C43 | 0.0 |
C27—C21—C22—C23 | 180.0 | C47—C41—C42—C43 | −180.0 |
C22—C21—C26—C25 | 0.0 | C42—C41—C46—C45 | 0.0 |
C27—C21—C26—C25 | −180.0 | C47—C41—C46—C45 | −180.0 |
C22—C21—C27—O28 | −4.2 (2) | C42—C41—C47—O48 | 4.1 (3) |
C22—C21—C27—O29 | 179.6 (2) | C42—C41—C47—O49 | −161.6 (2) |
C26—C21—C27—O28 | 175.8 (2) | C46—C41—C47—O48 | −175.9 (3) |
C26—C21—C27—O29 | −0.4 (2) | C46—C41—C47—O49 | 18.4 (2) |
C21—C22—C23—C24 | 0.0 | C41—C42—C43—C44 | −0.0 |
C22—C23—C24—C25 | −0.0 | C42—C43—C44—C45 | −0.0 |
C22—C23—C24—N212 | −180.0 | C42—C43—C44—N412 | −180.0 |
C23—C24—C25—C26 | 0.0 | C43—C44—C45—C46 | 0.0 |
N212—C24—C25—C26 | 180.0 | N412—C44—C45—C46 | −180.0 |
C24—C25—C26—C21 | −0.0 | C44—C45—C46—C41 | −0.0 |
C21—C27—O29—C210 | 179.3 (2) | C41—C47—O49—C410 | 174.2 (2) |
O28—C27—O29—C210 | 3.0 (4) | O48—C47—O49—C410 | 7.9 (4) |
C27—O29—C210—C211 | 179.4 (3) | C47—O49—C410—C411 | 173.3 (3) |
Symmetry codes: (i) −x+1, −y+1, z+1/2; (ii) x−1, y, z; (iii) x+1, y, z; (iv) x−1, y−1, z; (v) x, y+1, z; (vi) x−1, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N112—H2N112···O18ii | 1.00 | 1.98 | 2.941 (3) | 161 |
N212—H2N212···O28iii | 1.00 | 1.99 | 2.941 (3) | 158 |
N312—H2N312···O38ii | 1.00 | 2.04 | 2.962 (3) | 153 |
N412—H2N412···O48iii | 1.00 | 1.99 | 2.943 (3) | 158 |
N112—H1N112···N412ii | 1.00 | 3.25 | 4.094 (3) | 143 |
N212—H1N212···N112iii | 1.00 | 2.22 | 3.219 (3) | 176 |
N312—H1N312···N212ii | 1.00 | 2.20 | 3.196 (3) | 174 |
N412—H1N412···N312vii | 1.00 | 2.13 | 3.124 (3) | 170 |
N112—H1N112···C44ii | 1.00 | 2.56 | 3.513 (3) | 160 |
N212—H1N212···C14iii | 1.00 | 2.48 | 3.382 (3) | 151 |
N312—H1N312···C24ii | 1.00 | 2.63 | 3.481 (2) | 143 |
N412—H1N412···C34vii | 1.00 | 2.61 | 3.438 (3) | 141 |
Symmetry codes: (ii) x−1, y, z; (iii) x+1, y, z; (vii) x+1, y−1, z. |