Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616010792/qs3055sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616010792/qs3055Isup2.hkl | |
Text file https://doi.org/10.1107/S2053229616010792/qs3055sup3.txt | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616010792/qs3055Isup4.cml | |
Moving Picture Experts Group (MPG) video file https://doi.org/10.1107/S2053229616010792/qs3055sup5.mpg |
CCDC reference: 1489810
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009) and SADABS (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2006) and XP (Bruker, 1998); software used to prepare material for publication: PLATON(Spek, 2009).
C19H23NO4 | F(000) = 704 |
Mr = 329.38 | Dx = 1.322 Mg m−3 |
Triclinic, P1 | Melting point: 423(2) K |
a = 7.429 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.535 (4) Å | Cell parameters from 1135 reflections |
c = 15.675 (4) Å | θ = 2.7–26.1° |
α = 97.575 (5)° | µ = 0.09 mm−1 |
β = 98.902 (5)° | T = 100 K |
γ = 92.280 (5)° | Plate, colourless |
V = 1654.5 (8) Å3 | 0.27 × 0.23 × 0.12 mm |
Z = 4 |
Bruker D8 gonimeter with APEX CCD detector diffractometer | 6783 independent reflections |
Radiation source: Incoatec microsource | 3681 reflections with I > 2σ(I) |
Multilayer optics monochromator | Rint = 0.077 |
ω scans | θmax = 26.5°, θmin = 1.3° |
Absorption correction: multi-scan SADABS | h = −9→9 |
Tmin = 0.870, Tmax = 1.000 | k = −18→18 |
15196 measured reflections | l = −18→19 |
Refinement on F2 | 1 restraint |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.069 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.207 | w = 1/[σ2(Fo2) + (0.0729P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
6783 reflections | Δρmax = 0.63 e Å−3 |
450 parameters | Δρmin = −0.34 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 | ||
O1A | −0.3448 (3) | 0.24278 (13) | 0.06134 (13) | 0.0195 (5) | |
O2A | −0.2966 (3) | 0.28107 (13) | 0.22977 (13) | 0.0168 (5) | |
O3A | 0.1844 (3) | 0.63449 (14) | 0.22201 (14) | 0.0200 (5) | |
O4A | 0.6188 (3) | 0.66138 (15) | 0.15204 (16) | 0.0352 (6) | |
C1A | 0.2990 (4) | 0.45144 (18) | 0.24057 (18) | 0.0147 (6) | |
H1AA | 0.3770 | 0.4032 | 0.2642 | 0.018* | |
N2A | 0.4025 (3) | 0.50248 (15) | 0.18498 (15) | 0.0159 (6) | |
C3A | 0.4158 (4) | 0.44272 (19) | 0.10300 (18) | 0.0184 (7) | |
H3AB | 0.4649 | 0.3829 | 0.1161 | 0.022* | |
H3AC | 0.5008 | 0.4733 | 0.0711 | 0.022* | |
C4A | 0.2292 (4) | 0.4248 (2) | 0.04660 (19) | 0.0196 (7) | |
H4AB | 0.1886 | 0.4834 | 0.0263 | 0.023* | |
H4AC | 0.2374 | 0.3793 | −0.0053 | 0.023* | |
C4AA | 0.0910 (4) | 0.38763 (18) | 0.09676 (18) | 0.0142 (6) | |
C5A | −0.0670 (4) | 0.33535 (18) | 0.05310 (19) | 0.0163 (7) | |
H5AA | −0.0889 | 0.3253 | −0.0088 | 0.020* | |
C6A | −0.1917 (4) | 0.29820 (18) | 0.09802 (19) | 0.0158 (7) | |
C7A | −0.1623 (4) | 0.31675 (18) | 0.18979 (19) | 0.0148 (6) | |
C8A | −0.0085 (4) | 0.36796 (18) | 0.23302 (19) | 0.0144 (6) | |
H8AA | 0.0105 | 0.3801 | 0.2949 | 0.017* | |
C8AA | 0.1222 (4) | 0.40294 (17) | 0.18712 (18) | 0.0130 (6) | |
C9A | −0.3725 (4) | 0.2178 (2) | −0.03157 (19) | 0.0259 (8) | |
H9AA | −0.4851 | 0.1780 | −0.0502 | 0.039* | |
H9AB | −0.2690 | 0.1840 | −0.0484 | 0.039* | |
H9AC | −0.3824 | 0.2742 | −0.0596 | 0.039* | |
C10A | −0.2730 (4) | 0.30182 (19) | 0.32285 (18) | 0.0169 (7) | |
H10A | −0.3764 | 0.2735 | 0.3440 | 0.025* | |
H10B | −0.2668 | 0.3694 | 0.3398 | 0.025* | |
H10C | −0.1596 | 0.2768 | 0.3484 | 0.025* | |
C11A | 0.2551 (4) | 0.51777 (18) | 0.31612 (19) | 0.0150 (6) | |
C12A | 0.1880 (4) | 0.60489 (19) | 0.30116 (19) | 0.0164 (7) | |
C13A | 0.1253 (4) | 0.6610 (2) | 0.3680 (2) | 0.0230 (7) | |
H13A | 0.0771 | 0.7189 | 0.3579 | 0.028* | |
C14A | 0.1333 (4) | 0.6326 (2) | 0.4490 (2) | 0.0261 (8) | |
H14A | 0.0892 | 0.6711 | 0.4942 | 0.031* | |
C15A | 0.2047 (4) | 0.5490 (2) | 0.4656 (2) | 0.0247 (7) | |
H15A | 0.2110 | 0.5305 | 0.5219 | 0.030* | |
C16A | 0.2667 (4) | 0.4927 (2) | 0.39925 (19) | 0.0192 (7) | |
H16A | 0.3182 | 0.4360 | 0.4108 | 0.023* | |
C17A | 0.5854 (4) | 0.53435 (19) | 0.23653 (19) | 0.0191 (7) | |
H17A | 0.6494 | 0.4791 | 0.2526 | 0.023* | |
H17B | 0.5677 | 0.5727 | 0.2913 | 0.023* | |
C18A | 0.7059 (4) | 0.5898 (2) | 0.1906 (2) | 0.0287 (8) | |
H18A | 0.8135 | 0.6171 | 0.2330 | 0.034* | |
H18B | 0.7505 | 0.5472 | 0.1448 | 0.034* | |
O1B | 1.3476 (3) | 1.24568 (13) | 0.44849 (13) | 0.0209 (5) | |
O2B | 1.3051 (3) | 1.20930 (13) | 0.27953 (12) | 0.0171 (5) | |
O3B | 0.8447 (3) | 0.85566 (14) | 0.27042 (14) | 0.0211 (5) | |
O4B | 0.4333 (3) | 0.79004 (14) | 0.26269 (16) | 0.0321 (6) | |
H4B | 0.3627 | 0.7419 | 0.2540 | 0.048* | |
C1B | 0.7079 (4) | 1.03872 (18) | 0.26227 (18) | 0.0143 (6) | |
H1BA | 0.6287 | 1.0878 | 0.2411 | 0.017* | |
N2B | 0.6054 (3) | 0.98426 (15) | 0.31472 (15) | 0.0152 (5) | |
C3B | 0.5857 (4) | 1.04279 (19) | 0.39695 (19) | 0.0179 (7) | |
H3BB | 0.5009 | 1.0102 | 0.4275 | 0.022* | |
H3BC | 0.5333 | 1.1019 | 0.3837 | 0.022* | |
C4B | 0.7691 (4) | 1.0635 (2) | 0.45557 (19) | 0.0214 (7) | |
H4BB | 0.7562 | 1.1094 | 0.5065 | 0.026* | |
H4BC | 0.8113 | 1.0058 | 0.4773 | 0.026* | |
C4AB | 0.9088 (4) | 1.10145 (18) | 0.40675 (19) | 0.0153 (6) | |
C5B | 1.0653 (4) | 1.15457 (18) | 0.45301 (19) | 0.0164 (7) | |
H5BA | 1.0822 | 1.1655 | 0.5149 | 0.020* | |
C6B | 1.1944 (4) | 1.19102 (19) | 0.40984 (19) | 0.0174 (7) | |
C7B | 1.1692 (4) | 1.17373 (18) | 0.31776 (18) | 0.0147 (6) | |
C8B | 1.0152 (4) | 1.12234 (18) | 0.27287 (18) | 0.0159 (7) | |
H8BA | 0.9985 | 1.1108 | 0.2110 | 0.019* | |
C8AB | 0.8828 (4) | 1.08680 (18) | 0.31683 (18) | 0.0140 (6) | |
C9B | 1.3754 (4) | 1.2652 (2) | 0.5419 (2) | 0.0336 (9) | |
H9BA | 1.4876 | 1.3049 | 0.5624 | 0.050* | |
H9BB | 1.3859 | 1.2068 | 0.5667 | 0.050* | |
H9BC | 1.2715 | 1.2974 | 0.5605 | 0.050* | |
C10B | 1.2852 (4) | 1.18878 (19) | 0.18655 (18) | 0.0167 (7) | |
H10D | 1.3913 | 1.2160 | 0.1666 | 0.025* | |
H10E | 1.1741 | 1.2151 | 0.1600 | 0.025* | |
H10F | 1.2765 | 1.1212 | 0.1694 | 0.025* | |
C11B | 0.7515 (4) | 0.97668 (18) | 0.18348 (19) | 0.0148 (6) | |
C12B | 0.8260 (4) | 0.89027 (18) | 0.19270 (19) | 0.0159 (7) | |
C13B | 0.8859 (4) | 0.8394 (2) | 0.12260 (19) | 0.0208 (7) | |
H13B | 0.9384 | 0.7817 | 0.1290 | 0.025* | |
C14B | 0.8695 (4) | 0.8728 (2) | 0.0427 (2) | 0.0252 (8) | |
H14B | 0.9125 | 0.8381 | −0.0049 | 0.030* | |
C15B | 0.7910 (4) | 0.9561 (2) | 0.0319 (2) | 0.0227 (7) | |
H15B | 0.7780 | 0.9781 | −0.0230 | 0.027* | |
C16B | 0.7316 (4) | 1.0070 (2) | 0.10222 (19) | 0.0187 (7) | |
H16B | 0.6762 | 1.0638 | 0.0948 | 0.022* | |
C17B | 0.4210 (4) | 0.95446 (19) | 0.2650 (2) | 0.0199 (7) | |
H17C | 0.4292 | 0.9418 | 0.2021 | 0.024* | |
H17D | 0.3391 | 1.0059 | 0.2730 | 0.024* | |
C18B | 0.3386 (4) | 0.8684 (2) | 0.2929 (2) | 0.0249 (8) | |
H18C | 0.3500 | 0.8757 | 0.3572 | 0.030* | |
H18D | 0.2074 | 0.8592 | 0.2678 | 0.030* | |
H3B | 0.776 (5) | 0.887 (2) | 0.296 (2) | 0.035 (11)* | |
H3A | 0.248 (5) | 0.596 (2) | 0.192 (2) | 0.044 (11)* | |
H4A | 0.592 (4) | 0.6996 (17) | 0.2102 (13) | 0.015 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0178 (11) | 0.0203 (11) | 0.0172 (11) | −0.0023 (9) | −0.0013 (9) | −0.0035 (9) |
O2A | 0.0155 (10) | 0.0182 (11) | 0.0163 (11) | −0.0042 (8) | 0.0040 (9) | 0.0002 (8) |
O3A | 0.0224 (12) | 0.0153 (11) | 0.0218 (12) | 0.0022 (9) | 0.0029 (10) | 0.0011 (9) |
O4A | 0.0399 (15) | 0.0299 (13) | 0.0369 (16) | 0.0027 (11) | 0.0049 (12) | 0.0097 (11) |
C1A | 0.0170 (15) | 0.0100 (14) | 0.0167 (16) | −0.0017 (11) | 0.0024 (12) | 0.0014 (12) |
N2A | 0.0153 (12) | 0.0147 (12) | 0.0180 (14) | −0.0008 (10) | 0.0057 (11) | 0.0001 (10) |
C3A | 0.0232 (16) | 0.0172 (15) | 0.0164 (16) | 0.0016 (12) | 0.0106 (13) | −0.0002 (12) |
C4A | 0.0248 (17) | 0.0173 (15) | 0.0161 (17) | −0.0005 (13) | 0.0043 (13) | 0.0001 (12) |
C4AA | 0.0185 (15) | 0.0091 (14) | 0.0158 (16) | 0.0045 (11) | 0.0048 (12) | 0.0008 (12) |
C5A | 0.0193 (15) | 0.0146 (14) | 0.0145 (16) | 0.0033 (12) | 0.0020 (13) | 0.0006 (12) |
C6A | 0.0125 (14) | 0.0124 (14) | 0.0203 (17) | 0.0025 (11) | −0.0017 (13) | −0.0020 (12) |
C7A | 0.0138 (14) | 0.0116 (14) | 0.0201 (17) | 0.0023 (11) | 0.0054 (12) | 0.0025 (12) |
C8A | 0.0153 (15) | 0.0110 (14) | 0.0160 (16) | 0.0018 (11) | 0.0013 (12) | −0.0002 (12) |
C8AA | 0.0146 (14) | 0.0074 (13) | 0.0164 (16) | 0.0020 (11) | 0.0026 (12) | −0.0007 (11) |
C9A | 0.0224 (17) | 0.0330 (18) | 0.0178 (18) | −0.0029 (14) | −0.0021 (14) | −0.0055 (14) |
C10A | 0.0185 (15) | 0.0163 (15) | 0.0159 (16) | −0.0007 (12) | 0.0059 (13) | −0.0007 (12) |
C11A | 0.0115 (14) | 0.0115 (14) | 0.0204 (17) | −0.0024 (11) | 0.0016 (12) | −0.0015 (12) |
C12A | 0.0126 (14) | 0.0166 (15) | 0.0185 (17) | −0.0023 (12) | 0.0006 (12) | 0.0001 (12) |
C13A | 0.0170 (16) | 0.0180 (16) | 0.031 (2) | −0.0022 (12) | 0.0026 (14) | −0.0034 (14) |
C14A | 0.0244 (17) | 0.0259 (18) | 0.0239 (19) | −0.0032 (14) | 0.0066 (14) | −0.0139 (14) |
C15A | 0.0274 (18) | 0.0311 (18) | 0.0144 (17) | −0.0035 (14) | 0.0042 (14) | −0.0005 (14) |
C16A | 0.0200 (16) | 0.0173 (15) | 0.0195 (17) | −0.0036 (12) | 0.0029 (13) | 0.0018 (13) |
C17A | 0.0161 (15) | 0.0198 (16) | 0.0207 (17) | −0.0001 (12) | 0.0019 (13) | 0.0016 (13) |
C18A | 0.0232 (17) | 0.0342 (19) | 0.028 (2) | −0.0044 (14) | 0.0002 (15) | 0.0096 (15) |
O1B | 0.0162 (11) | 0.0231 (11) | 0.0192 (12) | −0.0025 (9) | −0.0023 (9) | −0.0051 (9) |
O2B | 0.0162 (11) | 0.0180 (10) | 0.0160 (11) | −0.0038 (8) | 0.0026 (9) | −0.0004 (8) |
O3B | 0.0250 (12) | 0.0187 (11) | 0.0212 (13) | 0.0071 (10) | 0.0061 (10) | 0.0034 (9) |
O4B | 0.0314 (13) | 0.0213 (12) | 0.0436 (16) | 0.0007 (10) | 0.0096 (12) | 0.0000 (11) |
C1B | 0.0148 (14) | 0.0138 (14) | 0.0133 (16) | −0.0017 (11) | 0.0020 (12) | −0.0004 (12) |
N2B | 0.0135 (12) | 0.0165 (12) | 0.0157 (13) | 0.0000 (10) | 0.0040 (10) | 0.0006 (10) |
C3B | 0.0168 (15) | 0.0179 (15) | 0.0194 (17) | −0.0005 (12) | 0.0067 (13) | −0.0003 (12) |
C4B | 0.0243 (17) | 0.0240 (16) | 0.0157 (17) | 0.0007 (13) | 0.0038 (13) | 0.0017 (13) |
C4AB | 0.0193 (15) | 0.0083 (13) | 0.0187 (16) | 0.0036 (11) | 0.0041 (13) | 0.0012 (11) |
C5B | 0.0208 (16) | 0.0142 (14) | 0.0131 (16) | 0.0056 (12) | 0.0000 (13) | 0.0004 (12) |
C6B | 0.0168 (15) | 0.0144 (15) | 0.0190 (17) | 0.0026 (12) | −0.0003 (13) | −0.0014 (12) |
C7B | 0.0138 (14) | 0.0131 (14) | 0.0163 (16) | 0.0012 (11) | 0.0024 (12) | −0.0010 (12) |
C8B | 0.0192 (15) | 0.0155 (14) | 0.0119 (16) | 0.0039 (12) | 0.0012 (13) | −0.0012 (12) |
C8AB | 0.0137 (14) | 0.0120 (14) | 0.0157 (16) | 0.0007 (11) | 0.0040 (12) | −0.0021 (12) |
C9B | 0.0235 (18) | 0.053 (2) | 0.0180 (18) | −0.0081 (16) | −0.0012 (14) | −0.0093 (16) |
C10B | 0.0155 (15) | 0.0178 (15) | 0.0159 (16) | −0.0038 (12) | 0.0039 (12) | −0.0002 (12) |
C11B | 0.0098 (14) | 0.0133 (14) | 0.0195 (17) | −0.0022 (11) | 0.0016 (12) | −0.0029 (12) |
C12B | 0.0135 (15) | 0.0127 (14) | 0.0203 (17) | −0.0005 (11) | 0.0008 (13) | 0.0014 (12) |
C13B | 0.0179 (16) | 0.0186 (16) | 0.0243 (19) | 0.0003 (13) | 0.0041 (14) | −0.0033 (13) |
C14B | 0.0205 (16) | 0.0286 (18) | 0.0230 (19) | −0.0033 (13) | 0.0077 (14) | −0.0122 (14) |
C15B | 0.0276 (17) | 0.0251 (17) | 0.0143 (17) | −0.0052 (14) | 0.0030 (14) | 0.0016 (13) |
C16B | 0.0203 (16) | 0.0173 (15) | 0.0159 (17) | −0.0035 (12) | −0.0011 (13) | −0.0012 (12) |
C17B | 0.0157 (15) | 0.0218 (16) | 0.0219 (18) | 0.0028 (12) | 0.0030 (13) | 0.0020 (13) |
C18B | 0.0218 (16) | 0.0216 (16) | 0.031 (2) | −0.0008 (13) | 0.0072 (14) | −0.0012 (14) |
O1A—C6A | 1.369 (3) | O1B—C6B | 1.371 (3) |
O1A—C9A | 1.434 (3) | O1B—C9B | 1.436 (3) |
O2A—C7A | 1.376 (3) | O2B—C7B | 1.369 (3) |
O2A—C10A | 1.432 (3) | O2B—C10B | 1.432 (3) |
O3A—C12A | 1.363 (3) | O3B—C12B | 1.368 (3) |
O3A—H3A | 0.88 (3) | O3B—H3B | 0.81 (3) |
O4A—C18A | 1.402 (4) | O4B—C18B | 1.428 (3) |
O4A—H4A | 1.054 (17) | O4B—H4B | 0.8400 |
C1A—N2A | 1.494 (4) | C1B—N2B | 1.483 (4) |
C1A—C11A | 1.510 (4) | C1B—C11B | 1.516 (4) |
C1A—C8AA | 1.534 (4) | C1B—C8AB | 1.528 (4) |
C1A—H1AA | 1.0000 | C1B—H1BA | 1.0000 |
N2A—C3A | 1.472 (3) | N2B—C3B | 1.478 (3) |
N2A—C17A | 1.492 (3) | N2B—C17B | 1.485 (3) |
C3A—C4A | 1.518 (4) | C3B—C4B | 1.516 (4) |
C3A—H3AB | 0.9900 | C3B—H3BB | 0.9900 |
C3A—H3AC | 0.9900 | C3B—H3BC | 0.9900 |
C4A—C4AA | 1.510 (4) | C4B—C4AB | 1.509 (4) |
C4A—H4AB | 0.9900 | C4B—H4BB | 0.9900 |
C4A—H4AC | 0.9900 | C4B—H4BC | 0.9900 |
C4AA—C8AA | 1.386 (4) | C4AB—C8AB | 1.379 (4) |
C4AA—C5A | 1.403 (4) | C4AB—C5B | 1.412 (4) |
C5A—C6A | 1.381 (4) | C5B—C6B | 1.383 (4) |
C5A—H5AA | 0.9500 | C5B—H5BA | 0.9500 |
C6A—C7A | 1.409 (4) | C6B—C7B | 1.414 (4) |
C7A—C8A | 1.371 (4) | C7B—C8B | 1.380 (4) |
C8A—C8AA | 1.411 (4) | C8B—C8AB | 1.405 (4) |
C8A—H8AA | 0.9500 | C8B—H8BA | 0.9500 |
C9A—H9AA | 0.9800 | C9B—H9BA | 0.9800 |
C9A—H9AB | 0.9800 | C9B—H9BB | 0.9800 |
C9A—H9AC | 0.9800 | C9B—H9BC | 0.9800 |
C10A—H10A | 0.9800 | C10B—H10D | 0.9800 |
C10A—H10B | 0.9800 | C10B—H10E | 0.9800 |
C10A—H10C | 0.9800 | C10B—H10F | 0.9800 |
C11A—C16A | 1.389 (4) | C11B—C16B | 1.390 (4) |
C11A—C12A | 1.414 (4) | C11B—C12B | 1.408 (4) |
C12A—C13A | 1.392 (4) | C12B—C13B | 1.384 (4) |
C13A—C14A | 1.379 (4) | C13B—C14B | 1.392 (4) |
C13A—H13A | 0.9500 | C13B—H13B | 0.9500 |
C14A—C15A | 1.385 (4) | C14B—C15B | 1.383 (4) |
C14A—H14A | 0.9500 | C14B—H14B | 0.9500 |
C15A—C16A | 1.385 (4) | C15B—C16B | 1.385 (4) |
C15A—H15A | 0.9500 | C15B—H15B | 0.9500 |
C16A—H16A | 0.9500 | C16B—H16B | 0.9500 |
C17A—C18A | 1.505 (4) | C17B—C18B | 1.516 (4) |
C17A—H17A | 0.9900 | C17B—H17C | 0.9900 |
C17A—H17B | 0.9900 | C17B—H17D | 0.9900 |
C18A—H18A | 0.9900 | C18B—H18C | 0.9900 |
C18A—H18B | 0.9900 | C18B—H18D | 0.9900 |
C6A—O1A—C9A | 116.8 (2) | C6B—O1B—C9B | 116.4 (2) |
C7A—O2A—C10A | 116.6 (2) | C7B—O2B—C10B | 116.5 (2) |
C12A—O3A—H3A | 106 (2) | C12B—O3B—H3B | 101 (2) |
C18A—O4A—H4A | 96.6 (15) | C18B—O4B—H4B | 109.5 |
N2A—C1A—C11A | 110.1 (2) | N2B—C1B—C11B | 110.4 (2) |
N2A—C1A—C8AA | 110.9 (2) | N2B—C1B—C8AB | 111.4 (2) |
C11A—C1A—C8AA | 109.9 (2) | C11B—C1B—C8AB | 110.4 (2) |
N2A—C1A—H1AA | 108.6 | N2B—C1B—H1BA | 108.2 |
C11A—C1A—H1AA | 108.6 | C11B—C1B—H1BA | 108.2 |
C8AA—C1A—H1AA | 108.6 | C8AB—C1B—H1BA | 108.2 |
C3A—N2A—C17A | 112.3 (2) | C3B—N2B—C1B | 109.5 (2) |
C3A—N2A—C1A | 110.4 (2) | C3B—N2B—C17B | 109.0 (2) |
C17A—N2A—C1A | 108.1 (2) | C1B—N2B—C17B | 109.5 (2) |
N2A—C3A—C4A | 110.2 (2) | N2B—C3B—C4B | 110.7 (2) |
N2A—C3A—H3AB | 109.6 | N2B—C3B—H3BB | 109.5 |
C4A—C3A—H3AB | 109.6 | C4B—C3B—H3BB | 109.5 |
N2A—C3A—H3AC | 109.6 | N2B—C3B—H3BC | 109.5 |
C4A—C3A—H3AC | 109.6 | C4B—C3B—H3BC | 109.5 |
H3AB—C3A—H3AC | 108.1 | H3BB—C3B—H3BC | 108.1 |
C4AA—C4A—C3A | 111.0 (2) | C4AB—C4B—C3B | 110.8 (2) |
C4AA—C4A—H4AB | 109.4 | C4AB—C4B—H4BB | 109.5 |
C3A—C4A—H4AB | 109.4 | C3B—C4B—H4BB | 109.5 |
C4AA—C4A—H4AC | 109.4 | C4AB—C4B—H4BC | 109.5 |
C3A—C4A—H4AC | 109.4 | C3B—C4B—H4BC | 109.5 |
H4AB—C4A—H4AC | 108.0 | H4BB—C4B—H4BC | 108.1 |
C8AA—C4AA—C5A | 119.2 (3) | C8AB—C4AB—C5B | 119.4 (3) |
C8AA—C4AA—C4A | 119.9 (3) | C8AB—C4AB—C4B | 120.6 (3) |
C5A—C4AA—C4A | 120.8 (3) | C5B—C4AB—C4B | 120.0 (3) |
C6A—C5A—C4AA | 121.6 (3) | C6B—C5B—C4AB | 121.2 (3) |
C6A—C5A—H5AA | 119.2 | C6B—C5B—H5BA | 119.4 |
C4AA—C5A—H5AA | 119.2 | C4AB—C5B—H5BA | 119.4 |
O1A—C6A—C5A | 125.7 (3) | O1B—C6B—C5B | 125.7 (3) |
O1A—C6A—C7A | 115.4 (3) | O1B—C6B—C7B | 115.2 (3) |
C5A—C6A—C7A | 118.9 (3) | C5B—C6B—C7B | 119.1 (3) |
C8A—C7A—O2A | 124.5 (3) | O2B—C7B—C8B | 124.6 (3) |
C8A—C7A—C6A | 119.9 (3) | O2B—C7B—C6B | 115.9 (2) |
O2A—C7A—C6A | 115.5 (2) | C8B—C7B—C6B | 119.4 (3) |
C7A—C8A—C8AA | 121.1 (3) | C7B—C8B—C8AB | 121.3 (3) |
C7A—C8A—H8AA | 119.5 | C7B—C8B—H8BA | 119.3 |
C8AA—C8A—H8AA | 119.5 | C8AB—C8B—H8BA | 119.3 |
C4AA—C8AA—C8A | 119.2 (3) | C4AB—C8AB—C8B | 119.5 (3) |
C4AA—C8AA—C1A | 122.9 (3) | C4AB—C8AB—C1B | 122.3 (3) |
C8A—C8AA—C1A | 117.7 (2) | C8B—C8AB—C1B | 118.1 (2) |
O1A—C9A—H9AA | 109.5 | O1B—C9B—H9BA | 109.5 |
O1A—C9A—H9AB | 109.5 | O1B—C9B—H9BB | 109.5 |
H9AA—C9A—H9AB | 109.5 | H9BA—C9B—H9BB | 109.5 |
O1A—C9A—H9AC | 109.5 | O1B—C9B—H9BC | 109.5 |
H9AA—C9A—H9AC | 109.5 | H9BA—C9B—H9BC | 109.5 |
H9AB—C9A—H9AC | 109.5 | H9BB—C9B—H9BC | 109.5 |
O2A—C10A—H10A | 109.5 | O2B—C10B—H10D | 109.5 |
O2A—C10A—H10B | 109.5 | O2B—C10B—H10E | 109.5 |
H10A—C10A—H10B | 109.5 | H10D—C10B—H10E | 109.5 |
O2A—C10A—H10C | 109.5 | O2B—C10B—H10F | 109.5 |
H10A—C10A—H10C | 109.5 | H10D—C10B—H10F | 109.5 |
H10B—C10A—H10C | 109.5 | H10E—C10B—H10F | 109.5 |
C16A—C11A—C12A | 118.8 (3) | C16B—C11B—C12B | 118.8 (3) |
C16A—C11A—C1A | 121.5 (2) | C16B—C11B—C1B | 120.6 (2) |
C12A—C11A—C1A | 119.5 (3) | C12B—C11B—C1B | 120.4 (3) |
O3A—C12A—C13A | 119.7 (3) | O3B—C12B—C13B | 118.6 (2) |
O3A—C12A—C11A | 120.7 (2) | O3B—C12B—C11B | 121.5 (3) |
C13A—C12A—C11A | 119.7 (3) | C13B—C12B—C11B | 119.9 (3) |
C14A—C13A—C12A | 120.0 (3) | C12B—C13B—C14B | 120.1 (3) |
C14A—C13A—H13A | 120.0 | C12B—C13B—H13B | 120.0 |
C12A—C13A—H13A | 120.0 | C14B—C13B—H13B | 120.0 |
C13A—C14A—C15A | 121.1 (3) | C15B—C14B—C13B | 120.7 (3) |
C13A—C14A—H14A | 119.4 | C15B—C14B—H14B | 119.7 |
C15A—C14A—H14A | 119.4 | C13B—C14B—H14B | 119.7 |
C16A—C15A—C14A | 119.1 (3) | C14B—C15B—C16B | 119.1 (3) |
C16A—C15A—H15A | 120.4 | C14B—C15B—H15B | 120.4 |
C14A—C15A—H15A | 120.4 | C16B—C15B—H15B | 120.4 |
C15A—C16A—C11A | 121.2 (3) | C15B—C16B—C11B | 121.4 (3) |
C15A—C16A—H16A | 119.4 | C15B—C16B—H16B | 119.3 |
C11A—C16A—H16A | 119.4 | C11B—C16B—H16B | 119.3 |
N2A—C17A—C18A | 114.9 (2) | N2B—C17B—C18B | 112.9 (2) |
N2A—C17A—H17A | 108.5 | N2B—C17B—H17C | 109.0 |
C18A—C17A—H17A | 108.5 | C18B—C17B—H17C | 109.0 |
N2A—C17A—H17B | 108.5 | N2B—C17B—H17D | 109.0 |
C18A—C17A—H17B | 108.5 | C18B—C17B—H17D | 109.0 |
H17A—C17A—H17B | 107.5 | H17C—C17B—H17D | 107.8 |
O4A—C18A—C17A | 113.8 (3) | O4B—C18B—C17B | 108.6 (2) |
O4A—C18A—H18A | 108.8 | O4B—C18B—H18C | 110.0 |
C17A—C18A—H18A | 108.8 | C17B—C18B—H18C | 110.0 |
O4A—C18A—H18B | 108.8 | O4B—C18B—H18D | 110.0 |
C17A—C18A—H18B | 108.8 | C17B—C18B—H18D | 110.0 |
H18A—C18A—H18B | 107.7 | H18C—C18B—H18D | 108.4 |
C11A—C1A—N2A—C3A | −169.4 (2) | C11B—C1B—N2B—C3B | 172.5 (2) |
C8AA—C1A—N2A—C3A | −47.6 (3) | C8AB—C1B—N2B—C3B | 49.5 (3) |
C11A—C1A—N2A—C17A | 67.4 (3) | C11B—C1B—N2B—C17B | −68.1 (3) |
C8AA—C1A—N2A—C17A | −170.7 (2) | C8AB—C1B—N2B—C17B | 168.9 (2) |
C17A—N2A—C3A—C4A | −171.1 (2) | C1B—N2B—C3B—C4B | −68.2 (3) |
C1A—N2A—C3A—C4A | 68.3 (3) | C17B—N2B—C3B—C4B | 172.0 (2) |
N2A—C3A—C4A—C4AA | −53.1 (3) | N2B—C3B—C4B—C4AB | 51.6 (3) |
C3A—C4A—C4AA—C8AA | 21.6 (3) | C3B—C4B—C4AB—C8AB | −20.3 (4) |
C3A—C4A—C4AA—C5A | −156.6 (2) | C3B—C4B—C4AB—C5B | 158.0 (2) |
C8AA—C4AA—C5A—C6A | −0.5 (4) | C8AB—C4AB—C5B—C6B | −1.0 (4) |
C4A—C4AA—C5A—C6A | 177.8 (2) | C4B—C4AB—C5B—C6B | −179.3 (2) |
C9A—O1A—C6A—C5A | 3.2 (4) | C9B—O1B—C6B—C5B | 0.8 (4) |
C9A—O1A—C6A—C7A | −176.2 (2) | C9B—O1B—C6B—C7B | 179.3 (2) |
C4AA—C5A—C6A—O1A | −176.7 (2) | C4AB—C5B—C6B—O1B | 177.9 (2) |
C4AA—C5A—C6A—C7A | 2.7 (4) | C4AB—C5B—C6B—C7B | −0.6 (4) |
C10A—O2A—C7A—C8A | 1.6 (4) | C10B—O2B—C7B—C8B | −1.7 (4) |
C10A—O2A—C7A—C6A | −177.8 (2) | C10B—O2B—C7B—C6B | 177.3 (2) |
O1A—C6A—C7A—C8A | 177.0 (2) | O1B—C6B—C7B—O2B | 3.4 (3) |
C5A—C6A—C7A—C8A | −2.4 (4) | C5B—C6B—C7B—O2B | −177.9 (2) |
O1A—C6A—C7A—O2A | −3.5 (3) | O1B—C6B—C7B—C8B | −177.6 (2) |
C5A—C6A—C7A—O2A | 177.1 (2) | C5B—C6B—C7B—C8B | 1.1 (4) |
O2A—C7A—C8A—C8AA | −179.4 (2) | O2B—C7B—C8B—C8AB | 179.0 (2) |
C6A—C7A—C8A—C8AA | 0.1 (4) | C6B—C7B—C8B—C8AB | 0.0 (4) |
C5A—C4AA—C8AA—C8A | −1.9 (4) | C5B—C4AB—C8AB—C8B | 2.1 (4) |
C4A—C4AA—C8AA—C8A | 179.8 (2) | C4B—C4AB—C8AB—C8B | −179.6 (2) |
C5A—C4AA—C8AA—C1A | 174.2 (2) | C5B—C4AB—C8AB—C1B | −173.6 (2) |
C4A—C4AA—C8AA—C1A | −4.0 (4) | C4B—C4AB—C8AB—C1B | 4.7 (4) |
C7A—C8A—C8AA—C4AA | 2.1 (4) | C7B—C8B—C8AB—C4AB | −1.6 (4) |
C7A—C8A—C8AA—C1A | −174.2 (2) | C7B—C8B—C8AB—C1B | 174.2 (2) |
N2A—C1A—C8AA—C4AA | 16.5 (3) | N2B—C1B—C8AB—C4AB | −19.1 (3) |
C11A—C1A—C8AA—C4AA | 138.5 (3) | C11B—C1B—C8AB—C4AB | −142.2 (3) |
N2A—C1A—C8AA—C8A | −167.3 (2) | N2B—C1B—C8AB—C8B | 165.2 (2) |
C11A—C1A—C8AA—C8A | −45.3 (3) | C11B—C1B—C8AB—C8B | 42.1 (3) |
N2A—C1A—C11A—C16A | −139.8 (3) | N2B—C1B—C11B—C16B | 137.2 (3) |
C8AA—C1A—C11A—C16A | 97.7 (3) | C8AB—C1B—C11B—C16B | −99.1 (3) |
N2A—C1A—C11A—C12A | 44.8 (3) | N2B—C1B—C11B—C12B | −47.7 (3) |
C8AA—C1A—C11A—C12A | −77.6 (3) | C8AB—C1B—C11B—C12B | 76.0 (3) |
C16A—C11A—C12A—O3A | 176.1 (2) | C16B—C11B—C12B—O3B | −178.3 (2) |
C1A—C11A—C12A—O3A | −8.4 (4) | C1B—C11B—C12B—O3B | 6.5 (4) |
C16A—C11A—C12A—C13A | −3.7 (4) | C16B—C11B—C12B—C13B | 3.1 (4) |
C1A—C11A—C12A—C13A | 171.7 (3) | C1B—C11B—C12B—C13B | −172.1 (2) |
O3A—C12A—C13A—C14A | −178.2 (3) | O3B—C12B—C13B—C14B | −179.8 (3) |
C11A—C12A—C13A—C14A | 1.7 (4) | C11B—C12B—C13B—C14B | −1.2 (4) |
C12A—C13A—C14A—C15A | 0.6 (4) | C12B—C13B—C14B—C15B | −1.0 (4) |
C13A—C14A—C15A—C16A | −0.8 (5) | C13B—C14B—C15B—C16B | 1.1 (4) |
C14A—C15A—C16A—C11A | −1.4 (4) | C14B—C15B—C16B—C11B | 0.8 (4) |
C12A—C11A—C16A—C15A | 3.6 (4) | C12B—C11B—C16B—C15B | −2.9 (4) |
C1A—C11A—C16A—C15A | −171.8 (3) | C1B—C11B—C16B—C15B | 172.2 (3) |
C3A—N2A—C17A—C18A | 59.7 (3) | C3B—N2B—C17B—C18B | −84.7 (3) |
C1A—N2A—C17A—C18A | −178.3 (2) | C1B—N2B—C17B—C18B | 155.6 (2) |
N2A—C17A—C18A—O4A | 48.4 (3) | N2B—C17B—C18B—O4B | −72.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3A—H3A···N2A | 0.88 (3) | 1.82 (4) | 2.625 (3) | 152 (3) |
O3B—H3B···N2B | 0.81 (3) | 1.96 (3) | 2.728 (3) | 157 (3) |
O4A—H4A···O4B | 1.05 (2) | 1.98 (2) | 2.915 (3) | 146 (2) |
O4B—H4B···O3A | 0.84 | 1.97 | 2.803 (3) | 174 |
C10A—H10A···O2Bi | 0.98 | 2.52 | 3.295 (3) | 137 |
C10B—H10D···O2Aii | 0.98 | 2.47 | 3.270 (3) | 138 |
Symmetry codes: (i) x−2, y−1, z; (ii) x+2, y+1, z. |
Number | Extinction condition | Average [I/σ(I)] | Number of reflections | I/σ(I) | T/F | |||||
True | False | True | False | Max. F | h | k | l | Ratio | ||
1 | hkl:h + k = 2N | 3.04 | 3.02 | 7596 | 7583 | 12.64 | -2 | -3 | 1 | 1.0 |
2 | hkl:h + l = 2N | 3.02 | 3.04 | 7600 | 7579 | 12.64 | -2 | -3 | 1 | 1.0 |
3 > A | hkl:k + l = 2N | 4.14 | 1.93 | 7567 | 7612 | 11.43 | -1 | -1 | 8 | 2.1 |