Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620000959/cu3158sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620000959/cu3158Iasup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620000959/cu3158Ibsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620000959/cu3158Icsup4.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620000959/cu3158Iasup5.cml |
CCDC references: 1979861; 1979860; 1979859
For all structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a). Program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b) for (Ia), (Ib); SHELXL2018 (Sheldrick, 2015b) for (Ic). For all structures, molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXTL (Bruker, 2016).
C7H9NO2 | Dx = 1.454 Mg m−3 |
Mr = 139.15 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 9965 reflections |
a = 7.185 (3) Å | θ = 3.0–30.5° |
b = 12.917 (6) Å | µ = 0.11 mm−1 |
c = 13.697 (6) Å | T = 100 K |
V = 1271.1 (9) Å3 | Needle, colorless |
Z = 8 | 0.28 × 0.14 × 0.12 mm |
F(000) = 592 |
Bruker D8 QUEST PHOTON-100 diffractometer | 1824 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.029 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 30.5°, θmin = 3.0° |
Tmin = 0.648, Tmax = 0.746 | h = −10→10 |
12849 measured reflections | k = −16→18 |
1936 independent reflections | l = −19→19 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0606P)2 + 0.6668P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max = 0.001 |
1936 reflections | Δρmax = 0.47 e Å−3 |
97 parameters | Δρmin = −0.21 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.41667 (13) | 0.44973 (7) | 0.21598 (7) | 0.00968 (19) | |
C2 | 0.42391 (13) | 0.46427 (7) | 0.31553 (7) | 0.00973 (19) | |
C3 | 0.36789 (13) | 0.38535 (7) | 0.38371 (7) | 0.01010 (19) | |
C4 | 0.30830 (14) | 0.29075 (7) | 0.34053 (7) | 0.01154 (19) | |
H4 | 0.269639 | 0.235180 | 0.381184 | 0.014* | |
C5 | 0.30593 (14) | 0.27876 (7) | 0.24132 (7) | 0.0118 (2) | |
H5 | 0.266703 | 0.214490 | 0.214600 | 0.014* | |
C6 | 0.35240 (15) | 0.33722 (8) | 0.07432 (7) | 0.0151 (2) | |
H6A | 0.316186 | 0.265298 | 0.061778 | 0.023* | |
H6B | 0.475850 | 0.350139 | 0.046435 | 0.023* | |
H6C | 0.261606 | 0.383954 | 0.044174 | 0.023* | |
C7 | 0.46748 (14) | 0.53325 (8) | 0.14518 (7) | 0.0127 (2) | |
H7A | 0.567947 | 0.508833 | 0.102612 | 0.019* | |
H7B | 0.509226 | 0.594649 | 0.181052 | 0.019* | |
H7C | 0.358562 | 0.550984 | 0.105488 | 0.019* | |
N1 | 0.35774 (11) | 0.35565 (6) | 0.18019 (6) | 0.01040 (18) | |
O1 | 0.48021 (11) | 0.55760 (6) | 0.35063 (5) | 0.01365 (18) | |
H1O | 0.505 (3) | 0.5515 (16) | 0.4166 (15) | 0.043 (6)* | |
O2 | 0.36942 (11) | 0.40280 (6) | 0.47503 (5) | 0.01410 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0094 (4) | 0.0097 (4) | 0.0099 (4) | 0.0004 (3) | −0.0002 (3) | 0.0000 (3) |
C2 | 0.0105 (4) | 0.0088 (4) | 0.0099 (4) | −0.0005 (3) | −0.0007 (3) | −0.0007 (3) |
C3 | 0.0098 (4) | 0.0107 (4) | 0.0098 (4) | 0.0002 (3) | 0.0001 (3) | −0.0001 (3) |
C4 | 0.0142 (4) | 0.0094 (4) | 0.0110 (4) | −0.0005 (3) | 0.0003 (3) | 0.0004 (3) |
C5 | 0.0139 (4) | 0.0095 (4) | 0.0121 (4) | 0.0000 (3) | −0.0007 (3) | −0.0013 (3) |
C6 | 0.0205 (5) | 0.0166 (4) | 0.0081 (4) | −0.0005 (4) | −0.0013 (3) | −0.0026 (3) |
C7 | 0.0146 (4) | 0.0133 (4) | 0.0101 (4) | −0.0010 (3) | −0.0002 (3) | 0.0028 (3) |
N1 | 0.0120 (4) | 0.0112 (4) | 0.0080 (3) | 0.0001 (3) | −0.0006 (3) | −0.0016 (3) |
O1 | 0.0208 (4) | 0.0104 (3) | 0.0097 (3) | −0.0040 (3) | −0.0017 (3) | −0.0011 (2) |
O2 | 0.0191 (4) | 0.0151 (3) | 0.0081 (3) | −0.0030 (3) | 0.0000 (2) | −0.0011 (2) |
C1—N1 | 1.3771 (13) | C5—H5 | 0.9500 |
C1—C2 | 1.3775 (14) | C6—N1 | 1.4700 (13) |
C1—C7 | 1.4958 (14) | C6—H6A | 0.9800 |
C2—O1 | 1.3595 (12) | C6—H6B | 0.9800 |
C2—C3 | 1.4399 (14) | C6—H6C | 0.9800 |
C3—O2 | 1.2709 (13) | C7—H7A | 0.9800 |
C3—C4 | 1.4234 (14) | C7—H7B | 0.9800 |
C4—C5 | 1.3679 (14) | C7—H7C | 0.9800 |
C4—H4 | 0.9500 | O1—H1O | 0.93 (2) |
C5—N1 | 1.3512 (13) | ||
N1—C1—C2 | 118.96 (8) | N1—C6—H6B | 109.5 |
N1—C1—C7 | 118.74 (9) | H6A—C6—H6B | 109.5 |
C2—C1—C7 | 122.29 (9) | N1—C6—H6C | 109.5 |
O1—C2—C1 | 118.83 (8) | H6A—C6—H6C | 109.5 |
O1—C2—C3 | 118.79 (9) | H6B—C6—H6C | 109.5 |
C1—C2—C3 | 122.34 (9) | C1—C7—H7A | 109.5 |
O2—C3—C4 | 124.32 (9) | C1—C7—H7B | 109.5 |
O2—C3—C2 | 120.68 (9) | H7A—C7—H7B | 109.5 |
C4—C3—C2 | 114.98 (9) | C1—C7—H7C | 109.5 |
C5—C4—C3 | 120.92 (9) | H7A—C7—H7C | 109.5 |
C5—C4—H4 | 119.5 | H7B—C7—H7C | 109.5 |
C3—C4—H4 | 119.5 | C5—N1—C1 | 120.85 (9) |
N1—C5—C4 | 121.93 (9) | C5—N1—C6 | 119.02 (9) |
N1—C5—H5 | 119.0 | C1—N1—C6 | 120.13 (8) |
C4—C5—H5 | 119.0 | C2—O1—H1O | 109.2 (13) |
N1—C6—H6A | 109.5 | ||
N1—C1—C2—O1 | −179.29 (8) | C2—C3—C4—C5 | −0.16 (13) |
C7—C1—C2—O1 | −0.38 (14) | C3—C4—C5—N1 | −0.66 (15) |
N1—C1—C2—C3 | −1.48 (14) | C4—C5—N1—C1 | 0.44 (14) |
C7—C1—C2—C3 | 177.43 (9) | C4—C5—N1—C6 | 179.77 (9) |
O1—C2—C3—O2 | 0.61 (14) | C2—C1—N1—C5 | 0.62 (13) |
C1—C2—C3—O2 | −177.20 (9) | C7—C1—N1—C5 | −178.33 (9) |
O1—C2—C3—C4 | 179.04 (8) | C2—C1—N1—C6 | −178.70 (9) |
C1—C2—C3—C4 | 1.23 (13) | C7—C1—N1—C6 | 2.34 (13) |
O2—C3—C4—C5 | 178.21 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O2i | 0.93 (2) | 1.83 (2) | 2.6704 (14) | 149.2 (18) |
C6—H6A···O2ii | 0.98 | 2.50 | 3.3878 (18) | 150 |
C7—H7C···O2iii | 0.98 | 2.50 | 3.4601 (15) | 168 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z−1/2; (iii) −x+1/2, −y+1, z−1/2. |
C7H9NO2 | F(000) = 296 |
Mr = 139.15 | Dx = 1.465 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 6.4847 (1) Å | Cell parameters from 5426 reflections |
b = 13.6853 (3) Å | θ = 2.7–30.5° |
c = 7.1462 (1) Å | µ = 0.11 mm−1 |
β = 95.6583 (8)° | T = 100 K |
V = 631.10 (2) Å3 | Block, colorless |
Z = 4 | 0.33 × 0.18 × 0.16 mm |
Bruker D8 QUEST PHOTON-100 diffractometer | 1681 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.029 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 30.5°, θmin = 3.0° |
Tmin = 0.705, Tmax = 0.746 | h = −9→9 |
7716 measured reflections | k = −19→19 |
1922 independent reflections | l = −10→10 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0495P)2 + 0.2705P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
1922 reflections | Δρmax = 0.43 e Å−3 |
97 parameters | Δρmin = −0.27 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.39396 (15) | 0.21544 (7) | 0.40876 (13) | 0.00929 (19) | |
C2 | 0.42242 (14) | 0.31466 (7) | 0.42168 (13) | 0.00901 (19) | |
C3 | 0.26323 (15) | 0.38332 (7) | 0.35673 (13) | 0.0097 (2) | |
C4 | 0.07167 (15) | 0.34026 (7) | 0.28596 (14) | 0.0117 (2) | |
H4 | −0.042505 | 0.381175 | 0.245672 | 0.014* | |
C5 | 0.04889 (15) | 0.24128 (7) | 0.27488 (14) | 0.0113 (2) | |
H5 | −0.080458 | 0.214858 | 0.224970 | 0.014* | |
C6 | 0.16938 (16) | 0.07400 (7) | 0.31937 (15) | 0.0136 (2) | |
H6A | 0.030437 | 0.061554 | 0.256977 | 0.020* | |
H6B | 0.180813 | 0.045615 | 0.445871 | 0.020* | |
H6C | 0.273046 | 0.044210 | 0.246263 | 0.020* | |
C7 | 0.56126 (15) | 0.14404 (7) | 0.47281 (14) | 0.0120 (2) | |
H7A | 0.594896 | 0.104351 | 0.365781 | 0.018* | |
H7B | 0.513253 | 0.101437 | 0.569862 | 0.018* | |
H7C | 0.685084 | 0.179601 | 0.524682 | 0.018* | |
N1 | 0.20509 (13) | 0.17983 (6) | 0.33287 (12) | 0.00950 (18) | |
O1 | 0.60952 (11) | 0.34951 (6) | 0.49501 (11) | 0.01269 (18) | |
H1O | 0.608 (3) | 0.4129 (15) | 0.515 (3) | 0.040 (5)* | |
O2 | 0.29796 (12) | 0.47457 (5) | 0.36221 (11) | 0.01408 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0100 (4) | 0.0095 (4) | 0.0082 (4) | 0.0001 (3) | 0.0000 (3) | 0.0003 (3) |
C2 | 0.0081 (4) | 0.0096 (4) | 0.0091 (4) | −0.0008 (3) | −0.0008 (3) | −0.0002 (3) |
C3 | 0.0107 (4) | 0.0086 (4) | 0.0094 (4) | 0.0000 (3) | −0.0004 (3) | 0.0007 (3) |
C4 | 0.0095 (4) | 0.0103 (4) | 0.0147 (4) | 0.0005 (3) | −0.0024 (3) | 0.0009 (3) |
C5 | 0.0095 (4) | 0.0109 (5) | 0.0130 (4) | −0.0011 (3) | −0.0011 (3) | 0.0010 (3) |
C6 | 0.0160 (5) | 0.0061 (4) | 0.0183 (5) | −0.0027 (3) | −0.0010 (4) | −0.0007 (4) |
C7 | 0.0121 (4) | 0.0095 (4) | 0.0138 (4) | 0.0028 (3) | −0.0016 (3) | −0.0001 (3) |
N1 | 0.0113 (4) | 0.0069 (4) | 0.0100 (4) | −0.0014 (3) | −0.0002 (3) | 0.0002 (3) |
O1 | 0.0091 (3) | 0.0087 (3) | 0.0191 (4) | −0.0011 (3) | −0.0041 (3) | −0.0019 (3) |
O2 | 0.0151 (3) | 0.0067 (3) | 0.0193 (4) | −0.0012 (3) | −0.0038 (3) | 0.0003 (3) |
C1—C2 | 1.3722 (13) | C5—H5 | 0.9500 |
C1—N1 | 1.3786 (12) | C6—N1 | 1.4684 (12) |
C1—C7 | 1.4978 (13) | C6—H6A | 0.9800 |
C2—O1 | 1.3597 (11) | C6—H6B | 0.9800 |
C2—C3 | 1.4386 (13) | C6—H6C | 0.9800 |
C3—O2 | 1.2689 (12) | C7—H7A | 0.9800 |
C3—C4 | 1.4220 (13) | C7—H7B | 0.9800 |
C4—C5 | 1.3642 (14) | C7—H7C | 0.9800 |
C4—H4 | 0.9500 | O1—H1O | 0.88 (2) |
C5—N1 | 1.3498 (13) | ||
C2—C1—N1 | 118.99 (9) | N1—C6—H6B | 109.5 |
C2—C1—C7 | 122.44 (9) | H6A—C6—H6B | 109.5 |
N1—C1—C7 | 118.57 (9) | N1—C6—H6C | 109.5 |
O1—C2—C1 | 118.82 (9) | H6A—C6—H6C | 109.5 |
O1—C2—C3 | 118.68 (9) | H6B—C6—H6C | 109.5 |
C1—C2—C3 | 122.49 (9) | C1—C7—H7A | 109.5 |
O2—C3—C4 | 124.40 (9) | C1—C7—H7B | 109.5 |
O2—C3—C2 | 120.89 (9) | H7A—C7—H7B | 109.5 |
C4—C3—C2 | 114.70 (9) | C1—C7—H7C | 109.5 |
C5—C4—C3 | 121.19 (9) | H7A—C7—H7C | 109.5 |
C5—C4—H4 | 119.4 | H7B—C7—H7C | 109.5 |
C3—C4—H4 | 119.4 | C5—N1—C1 | 120.75 (8) |
N1—C5—C4 | 121.81 (9) | C5—N1—C6 | 119.05 (8) |
N1—C5—H5 | 119.1 | C1—N1—C6 | 120.18 (8) |
C4—C5—H5 | 119.1 | C2—O1—H1O | 112.5 (12) |
N1—C6—H6A | 109.5 | ||
N1—C1—C2—O1 | −179.40 (8) | C2—C3—C4—C5 | −2.73 (14) |
C7—C1—C2—O1 | 0.13 (14) | C3—C4—C5—N1 | 1.04 (16) |
N1—C1—C2—C3 | −0.81 (14) | C4—C5—N1—C1 | 1.02 (14) |
C7—C1—C2—C3 | 178.71 (9) | C4—C5—N1—C6 | 179.19 (9) |
O1—C2—C3—O2 | 2.11 (14) | C2—C1—N1—C5 | −1.11 (13) |
C1—C2—C3—O2 | −176.48 (9) | C7—C1—N1—C5 | 179.34 (9) |
O1—C2—C3—C4 | −178.77 (8) | C2—C1—N1—C6 | −179.26 (9) |
C1—C2—C3—C4 | 2.65 (13) | C7—C1—N1—C6 | 1.20 (13) |
O2—C3—C4—C5 | 176.36 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O2i | 0.88 (2) | 1.85 (2) | 2.6602 (10) | 153.0 (17) |
C6—H6A···O2ii | 0.98 | 2.51 | 3.4560 (13) | 161 |
C7—H7A···O2iii | 0.98 | 2.55 | 3.5177 (13) | 168 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, y−1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2. |
C7H9NO2 | F(000) = 888 |
Mr = 139.15 | Dx = 1.452 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 19.4132 (8) Å | Cell parameters from 9985 reflections |
b = 13.7057 (7) Å | θ = 3.0–30.6° |
c = 7.1809 (7) Å | µ = 0.11 mm−1 |
β = 91.775 (1)° | T = 100 K |
V = 1909.7 (2) Å3 | Needle, colorless |
Z = 12 | 0.26 × 0.13 × 0.11 mm |
Bruker D8 QUEST PHOTON-100 diffractometer | 4477 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.033 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 30.6°, θmin = 2.6° |
Tmin = 0.679, Tmax = 0.746 | h = −27→27 |
24981 measured reflections | k = −19→15 |
5838 independent reflections | l = −10→9 |
Refinement on F2 | 1370 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.052P)2 + 1.601P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
5838 reflections | Δρmax = 0.42 e Å−3 |
467 parameters | Δρmin = −0.29 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1A | 0.46611 (6) | −0.28431 (9) | 0.57997 (17) | 0.0081 (2) | |
C2A | 0.47566 (6) | −0.18486 (9) | 0.57352 (18) | 0.0083 (2) | |
C3A | 0.42321 (7) | −0.11656 (9) | 0.62421 (18) | 0.0088 (2) | |
C4A | 0.35989 (7) | −0.15983 (10) | 0.67782 (18) | 0.0103 (2) | |
H4A | 0.322757 | −0.119246 | 0.712583 | 0.012* | |
C5A | 0.35208 (7) | −0.25888 (10) | 0.67973 (19) | 0.0104 (2) | |
H5A | 0.309225 | −0.285577 | 0.714803 | 0.012* | |
C6A | 0.39108 (7) | −0.42600 (10) | 0.6381 (2) | 0.0132 (3) | |
H6A | 0.400569 | −0.454201 | 0.516086 | 0.020* | |
H6B | 0.342955 | −0.438462 | 0.667873 | 0.020* | |
H6C | 0.421544 | −0.455852 | 0.733352 | 0.020* | |
C7A | 0.52179 (7) | −0.35513 (10) | 0.53413 (19) | 0.0111 (2) | |
H7A | 0.505416 | −0.398200 | 0.433206 | 0.017* | |
H7B | 0.533888 | −0.394246 | 0.644612 | 0.017* | |
H7C | 0.562504 | −0.319318 | 0.494576 | 0.017* | |
N1A | 0.40336 (6) | −0.32014 (8) | 0.63331 (15) | 0.0092 (2) | |
O1A | 0.53803 (5) | −0.14956 (7) | 0.52226 (14) | 0.0121 (2) | |
O2A | 0.43479 (5) | −0.02526 (7) | 0.62380 (14) | 0.0129 (2) | |
H1O | 0.5349 (12) | −0.0861 (17) | 0.496 (3) | 0.035 (6)* | |
C1B | 0.20010 (7) | 0.21488 (10) | 0.55646 (18) | 0.0086 (2) | 0.9456 (14) |
C2B | 0.19086 (7) | 0.31423 (10) | 0.54672 (18) | 0.0085 (2) | 0.9456 (14) |
C3B | 0.24321 (7) | 0.38244 (10) | 0.60838 (19) | 0.0087 (2) | 0.9456 (14) |
C4B | 0.30614 (8) | 0.33919 (12) | 0.6745 (2) | 0.0104 (4) | 0.9456 (14) |
H4B | 0.343028 | 0.379766 | 0.717195 | 0.013* | 0.9456 (14) |
C5B | 0.31408 (9) | 0.24015 (13) | 0.6772 (3) | 0.0107 (5) | 0.9456 (14) |
H5B | 0.356890 | 0.213449 | 0.719818 | 0.013* | 0.9456 (14) |
C6B | 0.27513 (8) | 0.07285 (10) | 0.6269 (2) | 0.0138 (3) | 0.9456 (14) |
H6D | 0.323089 | 0.060234 | 0.666315 | 0.021* | 0.9456 (14) |
H6E | 0.266237 | 0.045090 | 0.502713 | 0.021* | 0.9456 (14) |
H6F | 0.244218 | 0.042676 | 0.715590 | 0.021* | 0.9456 (14) |
C7B | 0.14437 (7) | 0.14403 (10) | 0.5019 (2) | 0.0115 (3) | 0.9456 (14) |
H7D | 0.102485 | 0.179857 | 0.464658 | 0.017* | 0.9456 (14) |
H7E | 0.134817 | 0.101691 | 0.607993 | 0.017* | 0.9456 (14) |
H7F | 0.159333 | 0.104167 | 0.397312 | 0.017* | 0.9456 (14) |
N1B | 0.26288 (6) | 0.17893 (9) | 0.62105 (17) | 0.0095 (2) | 0.9456 (14) |
O1B | 0.12887 (5) | 0.34919 (8) | 0.48237 (15) | 0.0121 (2) | 0.9456 (14) |
H2O | 0.131602 | 0.409816 | 0.467123 | 0.018* | 0.9456 (14) |
O2B | 0.23156 (5) | 0.47390 (7) | 0.60577 (15) | 0.0127 (2) | 0.9456 (14) |
C1B' | 0.2020 (9) | 0.2174 (11) | 0.803 (3) | 0.0099 (15) | 0.0544 (14) |
C2B' | 0.1915 (8) | 0.3184 (11) | 0.808 (3) | 0.0106 (15) | 0.0544 (14) |
C3B' | 0.2465 (9) | 0.3835 (11) | 0.776 (3) | 0.0087 (17) | 0.0544 (14) |
C4B' | 0.3099 (11) | 0.3438 (14) | 0.721 (5) | 0.0089 (18) | 0.0544 (14) |
H4B' | 0.346864 | 0.385747 | 0.690289 | 0.011* | 0.0544 (14) |
C5B' | 0.3179 (15) | 0.2420 (16) | 0.710 (8) | 0.0092 (18) | 0.0544 (14) |
H5B' | 0.359730 | 0.214846 | 0.668235 | 0.011* | 0.0544 (14) |
C6B' | 0.2787 (12) | 0.0730 (15) | 0.749 (4) | 0.009 (2) | 0.0544 (14) |
H6D' | 0.262181 | 0.041262 | 0.861222 | 0.014* | 0.0544 (14) |
H6E' | 0.328290 | 0.061280 | 0.739101 | 0.014* | 0.0544 (14) |
H6F' | 0.254291 | 0.046010 | 0.638909 | 0.014* | 0.0544 (14) |
C7B' | 0.1491 (12) | 0.1490 (18) | 0.850 (4) | 0.012 (2) | 0.0544 (14) |
H7D' | 0.125993 | 0.124732 | 0.736147 | 0.019* | 0.0544 (14) |
H7E' | 0.115336 | 0.181491 | 0.927872 | 0.019* | 0.0544 (14) |
H7F' | 0.169856 | 0.094149 | 0.919294 | 0.019* | 0.0544 (14) |
N1B' | 0.2653 (8) | 0.1827 (11) | 0.760 (3) | 0.0083 (16) | 0.0544 (14) |
O1B' | 0.1301 (9) | 0.3504 (14) | 0.869 (3) | 0.014 (2) | 0.0544 (14) |
H2O' | 0.132746 | 0.410381 | 0.892397 | 0.021* | 0.0544 (14) |
O2B' | 0.2346 (8) | 0.4742 (12) | 0.774 (2) | 0.0079 (19) | 0.0544 (14) |
C1C | 0.13170 (7) | 0.78333 (10) | 0.38435 (19) | 0.0093 (2) | 0.9579 (13) |
C2C | 0.14153 (7) | 0.68376 (10) | 0.39421 (19) | 0.0090 (2) | 0.9579 (13) |
C3C | 0.08816 (7) | 0.61553 (10) | 0.33973 (19) | 0.0092 (2) | 0.9579 (13) |
C4C | 0.02445 (7) | 0.65834 (10) | 0.2810 (2) | 0.0115 (3) | 0.9579 (13) |
H4C | −0.013496 | 0.617418 | 0.247973 | 0.014* | 0.9579 (13) |
C5C | 0.01680 (7) | 0.75751 (10) | 0.2710 (2) | 0.0110 (3) | 0.9579 (13) |
H5C | −0.026133 | 0.783893 | 0.228564 | 0.013* | 0.9579 (13) |
C6C | 0.05691 (8) | 0.92464 (10) | 0.3083 (2) | 0.0134 (3) | 0.9579 (13) |
H6G | 0.092073 | 0.954450 | 0.231512 | 0.020* | 0.9579 (13) |
H6H | 0.059634 | 0.952901 | 0.433672 | 0.020* | 0.9579 (13) |
H6I | 0.011137 | 0.937086 | 0.251898 | 0.020* | 0.9579 (13) |
C7C | 0.18718 (8) | 0.85467 (12) | 0.4391 (2) | 0.0117 (3) | 0.9579 (13) |
H7G | 0.199515 | 0.893173 | 0.330051 | 0.018* | 0.9579 (13) |
H7H | 0.227835 | 0.819242 | 0.487017 | 0.018* | 0.9579 (13) |
H7I | 0.170478 | 0.898276 | 0.535983 | 0.018* | 0.9579 (13) |
N1C | 0.06873 (6) | 0.81879 (8) | 0.32005 (16) | 0.0092 (2) | 0.9579 (13) |
O1C | 0.20417 (6) | 0.64901 (9) | 0.45377 (17) | 0.0128 (2) | 0.9579 (13) |
H3O | 0.201115 | 0.588978 | 0.475550 | 0.019* | 0.9579 (13) |
O2C | 0.09956 (5) | 0.52419 (7) | 0.34355 (15) | 0.0139 (2) | 0.9579 (13) |
C1C' | 0.1324 (12) | 0.7169 (15) | 0.448 (5) | 0.0093 (15) | 0.0421 (13) |
C2C' | 0.1439 (10) | 0.8177 (15) | 0.447 (5) | 0.0094 (17) | 0.0421 (13) |
C3C' | 0.0904 (11) | 0.8805 (13) | 0.506 (4) | 0.0100 (17) | 0.0421 (13) |
C4C' | 0.0281 (11) | 0.8388 (13) | 0.563 (4) | 0.0118 (19) | 0.0421 (13) |
H4C' | −0.007943 | 0.879755 | 0.604006 | 0.014* | 0.0421 (13) |
C5C' | 0.0190 (11) | 0.7370 (14) | 0.562 (4) | 0.0112 (18) | 0.0421 (13) |
H5C' | −0.023742 | 0.708783 | 0.593675 | 0.013* | 0.0421 (13) |
C6C' | 0.0602 (16) | 0.5701 (18) | 0.525 (4) | 0.011 (2) | 0.0421 (13) |
H6G' | 0.040155 | 0.554665 | 0.645254 | 0.017* | 0.0421 (13) |
H6H' | 0.104031 | 0.535264 | 0.514573 | 0.017* | 0.0421 (13) |
H6I' | 0.028398 | 0.549913 | 0.423873 | 0.017* | 0.0421 (13) |
C7C' | 0.1858 (19) | 0.647 (3) | 0.419 (6) | 0.011 (2) | 0.0421 (13) |
H7G' | 0.168763 | 0.596626 | 0.332446 | 0.016* | 0.0421 (13) |
H7H' | 0.199690 | 0.617262 | 0.537844 | 0.016* | 0.0421 (13) |
H7I' | 0.225525 | 0.680028 | 0.365532 | 0.016* | 0.0421 (13) |
N1C' | 0.0729 (10) | 0.6798 (12) | 0.513 (4) | 0.0102 (15) | 0.0421 (13) |
O1C' | 0.2068 (15) | 0.850 (2) | 0.397 (4) | 0.010 (2) | 0.0421 (13) |
H3O' | 0.232241 | 0.802362 | 0.374784 | 0.015* | 0.0421 (13) |
O2C' | 0.1006 (12) | 0.9709 (17) | 0.504 (3) | 0.011 (2) | 0.0421 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1A | 0.0091 (5) | 0.0081 (5) | 0.0071 (5) | 0.0000 (4) | 0.0000 (4) | 0.0007 (4) |
C2A | 0.0080 (5) | 0.0085 (5) | 0.0085 (6) | −0.0008 (4) | 0.0004 (4) | 0.0008 (4) |
C3A | 0.0097 (5) | 0.0086 (6) | 0.0082 (6) | 0.0000 (4) | −0.0001 (4) | 0.0001 (4) |
C4A | 0.0087 (5) | 0.0098 (6) | 0.0125 (6) | 0.0009 (4) | 0.0012 (4) | 0.0001 (4) |
C5A | 0.0088 (6) | 0.0101 (6) | 0.0123 (6) | −0.0011 (4) | 0.0005 (4) | 0.0007 (4) |
C6A | 0.0155 (6) | 0.0064 (5) | 0.0178 (7) | −0.0031 (5) | 0.0011 (5) | 0.0013 (5) |
C7A | 0.0123 (6) | 0.0080 (6) | 0.0130 (6) | 0.0023 (5) | 0.0012 (4) | 0.0006 (5) |
N1A | 0.0107 (5) | 0.0063 (5) | 0.0107 (5) | −0.0015 (4) | 0.0000 (4) | 0.0005 (4) |
O1A | 0.0094 (4) | 0.0083 (4) | 0.0189 (5) | −0.0013 (4) | 0.0042 (3) | 0.0023 (4) |
O2A | 0.0142 (5) | 0.0066 (4) | 0.0181 (5) | −0.0006 (3) | 0.0035 (4) | −0.0004 (3) |
C1B | 0.0094 (6) | 0.0081 (6) | 0.0084 (6) | −0.0005 (5) | 0.0008 (4) | 0.0002 (4) |
C2B | 0.0078 (5) | 0.0089 (6) | 0.0088 (6) | 0.0006 (5) | 0.0003 (4) | 0.0004 (4) |
C3B | 0.0098 (6) | 0.0077 (6) | 0.0086 (6) | −0.0001 (5) | 0.0011 (4) | 0.0000 (4) |
C4B | 0.0092 (6) | 0.0099 (6) | 0.0122 (9) | −0.0009 (5) | 0.0000 (5) | −0.0006 (5) |
C5B | 0.0087 (6) | 0.0106 (6) | 0.0127 (11) | 0.0010 (5) | 0.0000 (6) | 0.0015 (5) |
C6B | 0.0150 (7) | 0.0063 (6) | 0.0202 (8) | 0.0028 (5) | −0.0007 (5) | 0.0020 (5) |
C7B | 0.0125 (6) | 0.0092 (6) | 0.0127 (6) | −0.0029 (5) | 0.0002 (5) | −0.0003 (5) |
N1B | 0.0104 (5) | 0.0070 (5) | 0.0112 (5) | 0.0019 (4) | 0.0002 (4) | 0.0007 (4) |
O1B | 0.0095 (5) | 0.0075 (5) | 0.0191 (5) | 0.0003 (4) | −0.0043 (4) | 0.0013 (4) |
O2B | 0.0134 (5) | 0.0063 (5) | 0.0181 (5) | 0.0007 (4) | −0.0021 (4) | 0.0004 (4) |
C1B' | 0.009 (3) | 0.008 (3) | 0.012 (3) | 0.000 (3) | 0.000 (3) | 0.001 (3) |
C2B' | 0.010 (3) | 0.009 (3) | 0.014 (3) | 0.002 (3) | 0.000 (3) | −0.001 (3) |
C3B' | 0.009 (3) | 0.007 (3) | 0.010 (3) | 0.000 (3) | −0.001 (3) | 0.001 (3) |
C4B' | 0.008 (3) | 0.007 (3) | 0.012 (3) | 0.003 (3) | −0.001 (3) | 0.001 (3) |
C5B' | 0.008 (3) | 0.007 (3) | 0.012 (3) | −0.001 (3) | 0.000 (3) | 0.001 (3) |
C6B' | 0.010 (4) | 0.007 (4) | 0.012 (4) | 0.002 (4) | 0.000 (4) | 0.003 (4) |
C7B' | 0.012 (4) | 0.011 (4) | 0.014 (4) | −0.003 (4) | 0.002 (4) | 0.001 (4) |
N1B' | 0.007 (3) | 0.006 (3) | 0.011 (3) | 0.001 (3) | 0.000 (3) | 0.001 (3) |
O1B' | 0.012 (4) | 0.014 (4) | 0.016 (4) | 0.001 (4) | 0.001 (3) | 0.000 (4) |
O2B' | 0.008 (4) | 0.005 (4) | 0.011 (4) | 0.003 (3) | 0.000 (3) | −0.001 (3) |
C1C | 0.0097 (6) | 0.0084 (6) | 0.0097 (6) | −0.0003 (5) | 0.0003 (4) | 0.0002 (5) |
C2C | 0.0090 (6) | 0.0079 (6) | 0.0100 (6) | 0.0011 (5) | −0.0004 (4) | 0.0003 (5) |
C3C | 0.0109 (6) | 0.0076 (6) | 0.0091 (6) | 0.0006 (5) | −0.0004 (4) | −0.0011 (4) |
C4C | 0.0102 (6) | 0.0092 (6) | 0.0149 (6) | −0.0002 (5) | −0.0024 (5) | −0.0012 (5) |
C5C | 0.0096 (6) | 0.0109 (6) | 0.0125 (6) | 0.0014 (5) | −0.0016 (5) | −0.0002 (5) |
C6C | 0.0153 (6) | 0.0061 (6) | 0.0187 (7) | 0.0017 (5) | −0.0010 (5) | 0.0007 (5) |
C7C | 0.0117 (7) | 0.0094 (6) | 0.0140 (7) | −0.0033 (6) | −0.0009 (5) | 0.0007 (5) |
N1C | 0.0107 (5) | 0.0056 (5) | 0.0113 (5) | 0.0017 (4) | −0.0005 (4) | 0.0002 (4) |
O1C | 0.0102 (5) | 0.0085 (5) | 0.0194 (6) | 0.0017 (4) | −0.0043 (4) | 0.0022 (4) |
O2C | 0.0154 (5) | 0.0065 (5) | 0.0194 (5) | 0.0013 (4) | −0.0048 (4) | −0.0003 (4) |
C1C' | 0.009 (3) | 0.007 (3) | 0.012 (3) | 0.000 (3) | −0.002 (3) | −0.002 (3) |
C2C' | 0.010 (3) | 0.007 (3) | 0.012 (3) | −0.001 (3) | −0.003 (3) | 0.000 (3) |
C3C' | 0.011 (3) | 0.008 (3) | 0.011 (3) | 0.000 (3) | −0.002 (3) | 0.001 (3) |
C4C' | 0.013 (3) | 0.010 (3) | 0.013 (3) | 0.000 (3) | −0.002 (3) | 0.001 (3) |
C5C' | 0.012 (3) | 0.009 (3) | 0.012 (3) | 0.000 (3) | −0.001 (3) | 0.000 (3) |
C6C' | 0.012 (4) | 0.010 (4) | 0.012 (4) | −0.001 (4) | −0.001 (4) | 0.000 (4) |
C7C' | 0.011 (4) | 0.008 (3) | 0.012 (4) | −0.002 (3) | −0.002 (3) | 0.002 (3) |
N1C' | 0.011 (3) | 0.008 (3) | 0.011 (3) | 0.000 (3) | −0.002 (3) | 0.000 (3) |
O1C' | 0.010 (3) | 0.007 (3) | 0.012 (3) | −0.001 (3) | −0.001 (3) | −0.001 (3) |
O2C' | 0.012 (4) | 0.009 (4) | 0.013 (4) | 0.000 (3) | 0.001 (3) | 0.001 (3) |
C1A—C2A | 1.3767 (17) | C5B'—H5B' | 0.9500 |
C1A—N1A | 1.3786 (16) | C6B'—N1B' | 1.53 (2) |
C1A—C7A | 1.4969 (18) | C6B'—H6D' | 0.9800 |
C2A—O1A | 1.3649 (15) | C6B'—H6E' | 0.9800 |
C2A—C3A | 1.4383 (18) | C6B'—H6F' | 0.9800 |
C3A—O2A | 1.2713 (16) | C7B'—H7D' | 0.9800 |
C3A—C4A | 1.4285 (18) | C7B'—H7E' | 0.9800 |
C4A—C5A | 1.3660 (18) | C7B'—H7F' | 0.9800 |
C4A—H4A | 0.9500 | O1B'—H2O' | 0.8400 |
C5A—N1A | 1.3519 (17) | C1C—C2C | 1.3794 (19) |
C5A—H5A | 0.9500 | C1C—N1C | 1.3816 (17) |
C6A—N1A | 1.4708 (17) | C1C—C7C | 1.498 (2) |
C6A—H6A | 0.9800 | C2C—O1C | 1.3625 (17) |
C6A—H6B | 0.9800 | C2C—C3C | 1.4409 (19) |
C6A—H6C | 0.9800 | C3C—O2C | 1.2715 (16) |
C7A—H7A | 0.9800 | C3C—C4C | 1.4212 (18) |
C7A—H7B | 0.9800 | C4C—C5C | 1.3689 (19) |
C7A—H7C | 0.9800 | C4C—H4C | 0.9500 |
O1A—H1O | 0.89 (2) | C5C—N1C | 1.3505 (18) |
C1B—C2B | 1.3750 (19) | C5C—H5C | 0.9500 |
C1B—N1B | 1.3814 (17) | C6C—N1C | 1.4708 (18) |
C1B—C7B | 1.4968 (19) | C6C—H6G | 0.9800 |
C2B—O1B | 1.3627 (16) | C6C—H6H | 0.9800 |
C2B—C3B | 1.4405 (18) | C6C—H6I | 0.9800 |
C3B—O2B | 1.2738 (16) | C7C—H7G | 0.9800 |
C3B—C4B | 1.426 (2) | C7C—H7H | 0.9800 |
C4B—C5B | 1.366 (2) | C7C—H7I | 0.9800 |
C4B—H4B | 0.9500 | O1C—H3O | 0.8400 |
C5B—N1B | 1.353 (2) | C1C'—N1C' | 1.358 (16) |
C5B—H5B | 0.9500 | C1C'—C2C' | 1.400 (14) |
C6B—N1B | 1.4736 (18) | C1C'—C7C' | 1.43 (3) |
C6B—H6D | 0.9800 | C2C'—O1C' | 1.36 (3) |
C6B—H6E | 0.9800 | C2C'—C3C' | 1.423 (13) |
C6B—H6F | 0.9800 | C3C'—O2C' | 1.25 (3) |
C7B—H7D | 0.9800 | C3C'—C4C' | 1.412 (13) |
C7B—H7E | 0.9800 | C4C'—C5C' | 1.406 (14) |
C7B—H7F | 0.9800 | C4C'—H4C' | 0.9500 |
O1B—H2O | 0.8400 | C5C'—N1C' | 1.362 (16) |
C1B'—N1B' | 1.362 (15) | C5C'—H5C' | 0.9500 |
C1B'—C2B' | 1.400 (13) | C6C'—N1C' | 1.53 (2) |
C1B'—C7B' | 1.44 (3) | C6C'—H6G' | 0.9800 |
C2B'—O1B' | 1.36 (2) | C6C'—H6H' | 0.9800 |
C2B'—C3B' | 1.415 (13) | C6C'—H6I' | 0.9800 |
C3B'—O2B' | 1.26 (2) | C7C'—H7G' | 0.9800 |
C3B'—C4B' | 1.416 (13) | C7C'—H7H' | 0.9800 |
C4B'—C5B' | 1.406 (14) | C7C'—H7I' | 0.9800 |
C4B'—H4B' | 0.9500 | O1C'—H3O' | 0.8400 |
C5B'—N1B' | 1.361 (17) | ||
C2A—C1A—N1A | 118.89 (11) | N1B'—C6B'—H6E' | 109.5 |
C2A—C1A—C7A | 122.39 (11) | H6D'—C6B'—H6E' | 109.5 |
N1A—C1A—C7A | 118.71 (11) | N1B'—C6B'—H6F' | 109.5 |
O1A—C2A—C1A | 118.79 (11) | H6D'—C6B'—H6F' | 109.5 |
O1A—C2A—C3A | 118.59 (11) | H6E'—C6B'—H6F' | 109.5 |
C1A—C2A—C3A | 122.60 (12) | C1B'—C7B'—H7D' | 109.5 |
O2A—C3A—C4A | 124.27 (12) | C1B'—C7B'—H7E' | 109.5 |
O2A—C3A—C2A | 120.88 (12) | H7D'—C7B'—H7E' | 109.5 |
C4A—C3A—C2A | 114.83 (11) | C1B'—C7B'—H7F' | 109.5 |
C5A—C4A—C3A | 120.80 (12) | H7D'—C7B'—H7F' | 109.5 |
C5A—C4A—H4A | 119.6 | H7E'—C7B'—H7F' | 109.5 |
C3A—C4A—H4A | 119.6 | C5B'—N1B'—C1B' | 122.7 (15) |
N1A—C5A—C4A | 122.14 (12) | C5B'—N1B'—C6B' | 116.4 (16) |
N1A—C5A—H5A | 118.9 | C1B'—N1B'—C6B' | 120.7 (16) |
C4A—C5A—H5A | 118.9 | C2B'—O1B'—H2O' | 109.5 |
N1A—C6A—H6A | 109.5 | C2C—C1C—N1C | 119.00 (13) |
N1A—C6A—H6B | 109.5 | C2C—C1C—C7C | 122.35 (13) |
H6A—C6A—H6B | 109.5 | N1C—C1C—C7C | 118.65 (13) |
N1A—C6A—H6C | 109.5 | O1C—C2C—C1C | 118.86 (12) |
H6A—C6A—H6C | 109.5 | O1C—C2C—C3C | 119.06 (13) |
H6B—C6A—H6C | 109.5 | C1C—C2C—C3C | 122.07 (13) |
C1A—C7A—H7A | 109.5 | O2C—C3C—C4C | 124.21 (12) |
C1A—C7A—H7B | 109.5 | O2C—C3C—C2C | 120.66 (12) |
H7A—C7A—H7B | 109.5 | C4C—C3C—C2C | 115.12 (12) |
C1A—C7A—H7C | 109.5 | C5C—C4C—C3C | 121.16 (13) |
H7A—C7A—H7C | 109.5 | C5C—C4C—H4C | 119.4 |
H7B—C7A—H7C | 109.5 | C3C—C4C—H4C | 119.4 |
C5A—N1A—C1A | 120.73 (11) | N1C—C5C—C4C | 121.67 (13) |
C5A—N1A—C6A | 119.07 (11) | N1C—C5C—H5C | 119.2 |
C1A—N1A—C6A | 120.20 (11) | C4C—C5C—H5C | 119.2 |
C2A—O1A—H1O | 110.3 (15) | N1C—C6C—H6G | 109.5 |
C2B—C1B—N1B | 118.86 (12) | N1C—C6C—H6H | 109.5 |
C2B—C1B—C7B | 122.48 (12) | H6G—C6C—H6H | 109.5 |
N1B—C1B—C7B | 118.65 (12) | N1C—C6C—H6I | 109.5 |
O1B—C2B—C1B | 118.55 (12) | H6G—C6C—H6I | 109.5 |
O1B—C2B—C3B | 118.90 (12) | H6H—C6C—H6I | 109.5 |
C1B—C2B—C3B | 122.51 (12) | C1C—C7C—H7G | 109.5 |
O2B—C3B—C4B | 124.33 (13) | C1C—C7C—H7H | 109.5 |
O2B—C3B—C2B | 120.72 (12) | H7G—C7C—H7H | 109.5 |
C4B—C3B—C2B | 114.93 (12) | C1C—C7C—H7I | 109.5 |
C5B—C4B—C3B | 120.86 (14) | H7G—C7C—H7I | 109.5 |
C5B—C4B—H4B | 119.6 | H7H—C7C—H7I | 109.5 |
C3B—C4B—H4B | 119.6 | C5C—N1C—C1C | 120.93 (12) |
N1B—C5B—C4B | 122.04 (15) | C5C—N1C—C6C | 118.98 (12) |
N1B—C5B—H5B | 119.0 | C1C—N1C—C6C | 120.07 (12) |
C4B—C5B—H5B | 119.0 | C2C—O1C—H3O | 109.5 |
N1B—C6B—H6D | 109.5 | N1C'—C1C'—C2C' | 120.5 (14) |
N1B—C6B—H6E | 109.5 | N1C'—C1C'—C7C' | 115 (2) |
H6D—C6B—H6E | 109.5 | C2C'—C1C'—C7C' | 123 (2) |
N1B—C6B—H6F | 109.5 | O1C'—C2C'—C1C' | 118 (2) |
H6D—C6B—H6F | 109.5 | O1C'—C2C'—C3C' | 123 (2) |
H6E—C6B—H6F | 109.5 | C1C'—C2C'—C3C' | 118.6 (10) |
C1B—C7B—H7D | 109.5 | O2C'—C3C'—C4C' | 122.6 (19) |
C1B—C7B—H7E | 109.5 | O2C'—C3C'—C2C' | 118.6 (19) |
H7D—C7B—H7E | 109.5 | C4C'—C3C'—C2C' | 118.8 (11) |
C1B—C7B—H7F | 109.5 | C5C'—C4C'—C3C' | 120.5 (11) |
H7D—C7B—H7F | 109.5 | C5C'—C4C'—H4C' | 119.7 |
H7E—C7B—H7F | 109.5 | C3C'—C4C'—H4C' | 119.7 |
C5B—N1B—C1B | 120.75 (13) | N1C'—C5C'—C4C' | 118.4 (14) |
C5B—N1B—C6B | 119.15 (13) | N1C'—C5C'—H5C' | 120.8 |
C1B—N1B—C6B | 120.09 (12) | C4C'—C5C'—H5C' | 120.8 |
C2B—O1B—H2O | 109.5 | N1C'—C6C'—H6G' | 109.5 |
N1B'—C1B'—C2B' | 119.0 (12) | N1C'—C6C'—H6H' | 109.5 |
N1B'—C1B'—C7B' | 118.9 (16) | H6G'—C6C'—H6H' | 109.5 |
C2B'—C1B'—C7B' | 122.1 (17) | N1C'—C6C'—H6I' | 109.5 |
O1B'—C2B'—C1B' | 117.4 (15) | H6G'—C6C'—H6I' | 109.5 |
O1B'—C2B'—C3B' | 121.5 (15) | H6H'—C6C'—H6I' | 109.5 |
C1B'—C2B'—C3B' | 120.6 (10) | C1C'—C7C'—H7G' | 109.5 |
O2B'—C3B'—C2B' | 119.0 (16) | C1C'—C7C'—H7H' | 109.5 |
O2B'—C3B'—C4B' | 122.2 (16) | H7G'—C7C'—H7H' | 109.5 |
C2B'—C3B'—C4B' | 118.0 (10) | C1C'—C7C'—H7I' | 109.5 |
C5B'—C4B'—C3B' | 119.7 (11) | H7G'—C7C'—H7I' | 109.5 |
C5B'—C4B'—H4B' | 120.2 | H7H'—C7C'—H7I' | 109.5 |
C3B'—C4B'—H4B' | 120.2 | C1C'—N1C'—C5C' | 122.8 (15) |
N1B'—C5B'—C4B' | 119.5 (14) | C1C'—N1C'—C6C' | 121.9 (19) |
N1B'—C5B'—H5B' | 120.2 | C5C'—N1C'—C6C' | 115.1 (19) |
C4B'—C5B'—H5B' | 120.2 | C2C'—O1C'—H3O' | 109.5 |
N1B'—C6B'—H6D' | 109.5 | ||
N1A—C1A—C2A—O1A | 179.43 (11) | C2B'—C3B'—C4B'—C5B' | −4 (5) |
C7A—C1A—C2A—O1A | 0.44 (18) | C3B'—C4B'—C5B'—N1B' | −2 (7) |
N1A—C1A—C2A—C3A | 1.40 (19) | C4B'—C5B'—N1B'—C1B' | 7 (6) |
C7A—C1A—C2A—C3A | −177.59 (12) | C4B'—C5B'—N1B'—C6B' | −179 (4) |
O1A—C2A—C3A—O2A | −0.91 (18) | C2B'—C1B'—N1B'—C5B' | −4 (4) |
C1A—C2A—C3A—O2A | 177.13 (12) | C7B'—C1B'—N1B'—C5B' | 179 (3) |
O1A—C2A—C3A—C4A | −179.35 (11) | C2B'—C1B'—N1B'—C6B' | −179 (2) |
C1A—C2A—C3A—C4A | −1.32 (18) | C7B'—C1B'—N1B'—C6B' | 4 (3) |
O2A—C3A—C4A—C5A | −178.08 (13) | N1C—C1C—C2C—O1C | 178.56 (12) |
C2A—C3A—C4A—C5A | 0.31 (18) | C7C—C1C—C2C—O1C | −0.8 (2) |
C3A—C4A—C5A—N1A | 0.6 (2) | N1C—C1C—C2C—C3C | −0.1 (2) |
C4A—C5A—N1A—C1A | −0.6 (2) | C7C—C1C—C2C—C3C | −179.41 (13) |
C4A—C5A—N1A—C6A | −179.81 (12) | O1C—C2C—C3C—O2C | −1.3 (2) |
C2A—C1A—N1A—C5A | −0.41 (18) | C1C—C2C—C3C—O2C | 177.28 (13) |
C7A—C1A—N1A—C5A | 178.61 (12) | O1C—C2C—C3C—C4C | 179.54 (13) |
C2A—C1A—N1A—C6A | 178.80 (12) | C1C—C2C—C3C—C4C | −1.8 (2) |
C7A—C1A—N1A—C6A | −2.19 (17) | O2C—C3C—C4C—C5C | −176.53 (14) |
N1B—C1B—C2B—O1B | 179.82 (12) | C2C—C3C—C4C—C5C | 2.5 (2) |
C7B—C1B—C2B—O1B | −1.0 (2) | C3C—C4C—C5C—N1C | −1.4 (2) |
N1B—C1B—C2B—C3B | −2.6 (2) | C4C—C5C—N1C—C1C | −0.7 (2) |
C7B—C1B—C2B—C3B | 176.65 (13) | C4C—C5C—N1C—C6C | −179.27 (13) |
O1B—C2B—C3B—O2B | 1.1 (2) | C2C—C1C—N1C—C5C | 1.4 (2) |
C1B—C2B—C3B—O2B | −176.50 (13) | C7C—C1C—N1C—C5C | −179.22 (13) |
O1B—C2B—C3B—C4B | 179.60 (12) | C2C—C1C—N1C—C6C | 179.96 (13) |
C1B—C2B—C3B—C4B | 1.99 (19) | C7C—C1C—N1C—C6C | −0.67 (19) |
O2B—C3B—C4B—C5B | 178.31 (15) | N1C'—C1C'—C2C'—O1C' | 174 (3) |
C2B—C3B—C4B—C5B | −0.1 (2) | C7C'—C1C'—C2C'—O1C' | 7 (5) |
C3B—C4B—C5B—N1B | −1.2 (3) | N1C'—C1C'—C2C'—C3C' | −4 (5) |
C4B—C5B—N1B—C1B | 0.6 (2) | C7C'—C1C'—C2C'—C3C' | −170 (3) |
C4B—C5B—N1B—C6B | 179.73 (15) | O1C'—C2C'—C3C'—O2C' | 3 (5) |
C2B—C1B—N1B—C5B | 1.2 (2) | C1C'—C2C'—C3C'—O2C' | −180 (3) |
C7B—C1B—N1B—C5B | −178.03 (14) | O1C'—C2C'—C3C'—C4C' | −177 (3) |
C2B—C1B—N1B—C6B | −177.87 (13) | C1C'—C2C'—C3C'—C4C' | 1 (5) |
C7B—C1B—N1B—C6B | 2.88 (19) | O2C'—C3C'—C4C'—C5C' | 180 (3) |
N1B'—C1B'—C2B'—O1B' | −174 (2) | C2C'—C3C'—C4C'—C5C' | −1 (5) |
C7B'—C1B'—C2B'—O1B' | 3 (4) | C3C'—C4C'—C5C'—N1C' | 4 (5) |
N1B'—C1B'—C2B'—C3B' | −2 (4) | C2C'—C1C'—N1C'—C5C' | 7 (5) |
C7B'—C1B'—C2B'—C3B' | 174 (2) | C7C'—C1C'—N1C'—C5C' | 175 (3) |
O1B'—C2B'—C3B'—O2B' | −12 (4) | C2C'—C1C'—N1C'—C6C' | −177 (3) |
C1B'—C2B'—C3B'—O2B' | 177 (2) | C7C'—C1C'—N1C'—C6C' | −9 (5) |
O1B'—C2B'—C3B'—C4B' | 177 (3) | C4C'—C5C'—N1C'—C1C' | −7 (5) |
C1B'—C2B'—C3B'—C4B' | 6 (4) | C4C'—C5C'—N1C'—C6C' | 177 (3) |
O2B'—C3B'—C4B'—C5B' | −174 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1O···O2Ai | 0.89 (2) | 1.86 (2) | 2.6747 (14) | 151 (2) |
C6A—H6B···O2Bii | 0.98 | 2.50 | 3.3886 (17) | 150 |
C7A—H7B···O2Aiii | 0.98 | 2.51 | 3.4718 (17) | 167 |
O1B—H2O···O2C | 0.84 | 1.90 | 2.6524 (15) | 149 |
C6B—H6D···O2A | 0.98 | 2.49 | 3.3793 (18) | 150 |
C7B—H7E···O2Civ | 0.98 | 2.53 | 3.4962 (18) | 171 |
O1C—H3O···O2B | 0.84 | 1.92 | 2.6829 (16) | 151 |
C6C—H6I···O2Cv | 0.98 | 2.53 | 3.4745 (18) | 161 |
C7C—H7G···O2Bvi | 0.98 | 2.52 | 3.4814 (19) | 166 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y−1, z; (iii) −x+1, y−1/2, −z+3/2; (iv) x, −y+1/2, z+1/2; (v) −x, y+1/2, −z+1/2; (vi) x, −y+3/2, z−1/2. |