Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603337X/fl2048sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680603337X/fl2048Isup2.hkl |
CCDC reference: 621312
Key indicators
- Single-crystal X-ray study
- T = 113 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.038
- wR factor = 0.102
- Data-to-parameter ratio = 8.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.85 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.52 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.37 Ratio PLAT301_ALERT_3_C Main Residue Disorder ......................... 10.00 Perc. PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C6 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 13.00 Deg. C16 -N2 -C16' 1.555 1.555 1.555
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.86 From the CIF: _reflns_number_total 2244 Count of symmetry unique reflns 2246 Completeness (_total/calc) 99.91% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT792_ALERT_1_G Check the Absolute Configuration of C3 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: CrystalStructure.
C18H21N3O6 | Dx = 1.407 Mg m−3 |
Mr = 375.38 | Melting point = 473–474 K |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71070 Å |
a = 14.1028 (15) Å | Cell parameters from 5692 reflections |
b = 14.4948 (16) Å | θ = 2.0–27.9° |
c = 8.6701 (10) Å | µ = 0.11 mm−1 |
V = 1772.3 (3) Å3 | T = 113 K |
Z = 4 | Block, yellow |
F(000) = 792 | 0.26 × 0.20 × 0.16 mm |
Rigaku Saturn diffractometer | 2244 independent reflections |
Radiation source: rotating anode | 2066 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.039 |
Detector resolution: 7.31 pixels mm-1 | θmax = 27.9°, θmin = 2.0° |
ω scans | h = −18→18 |
Absorption correction: multi-scan Jacobson (1998) | k = −16→19 |
Tmin = 0.970, Tmax = 0.983 | l = −11→11 |
15964 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.038 | w = 1/[σ2(Fo2) + (0.0731P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.102 | (Δ/σ)max = 0.002 |
S = 1.06 | Δρmax = 0.28 e Å−3 |
2244 reflections | Δρmin = −0.21 e Å−3 |
279 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
34 restraints | Extinction coefficient: 0.034 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: 0 |
Secondary atom site location: difference Fourier map |
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 | Occ. (<1) | |
O1 | 0.41255 (10) | 0.19434 (11) | 0.8037 (2) | 0.0241 (4) | |
O2 | 0.53243 (10) | 0.10226 (11) | 0.8742 (2) | 0.0248 (4) | |
O3 | 0.58962 (11) | 0.51173 (10) | 0.4121 (2) | 0.0211 (3) | |
O5 | 0.21330 (12) | 0.39955 (14) | 0.3888 (3) | 0.0407 (5) | |
O6 | 0.19939 (13) | 0.31158 (17) | 0.1897 (3) | 0.0445 (6) | |
N1 | 0.72163 (13) | 0.29199 (13) | 0.6754 (2) | 0.0191 (4) | |
H1 | 0.7811 (19) | 0.2826 (18) | 0.697 (3) | 0.023* | |
N2 | 0.49400 (14) | 0.52288 (13) | 0.6202 (2) | 0.0232 (4) | |
H2 | 0.4790 (19) | 0.503 (2) | 0.712 (4) | 0.028* | |
N3 | 0.24354 (14) | 0.33973 (15) | 0.3014 (3) | 0.0286 (5) | |
C1 | 0.66328 (15) | 0.22799 (14) | 0.7421 (3) | 0.0177 (4) | |
C2 | 0.56740 (14) | 0.24015 (14) | 0.7363 (2) | 0.0164 (4) | |
C3 | 0.52234 (14) | 0.32048 (14) | 0.6515 (2) | 0.0158 (4) | |
H3 | 0.4760 | 0.3508 | 0.7226 | 0.019* | |
C4 | 0.59622 (14) | 0.39221 (14) | 0.6042 (3) | 0.0169 (4) | |
C5 | 0.68985 (15) | 0.37503 (15) | 0.6137 (3) | 0.0182 (4) | |
C6 | 0.71639 (15) | 0.14949 (16) | 0.8156 (3) | 0.0215 (5) | |
H6A | 0.7847 | 0.1589 | 0.8021 | 0.026* | |
H6B | 0.6977 | 0.0913 | 0.7667 | 0.026* | |
H6C | 0.7014 | 0.1471 | 0.9259 | 0.026* | |
C7 | 0.49785 (14) | 0.17853 (15) | 0.8062 (3) | 0.0179 (4) | |
C8 | 0.46328 (16) | 0.03724 (16) | 0.9323 (3) | 0.0279 (5) | |
H8A | 0.4961 | −0.0152 | 0.9797 | 0.034* | |
H8B | 0.4237 | 0.0152 | 0.8469 | 0.034* | |
H8C | 0.4232 | 0.0676 | 1.0094 | 0.034* | |
C9 | 0.46891 (15) | 0.28922 (15) | 0.5072 (3) | 0.0176 (4) | |
C10 | 0.38224 (15) | 0.32853 (15) | 0.4697 (3) | 0.0196 (4) | |
H10 | 0.3546 | 0.3744 | 0.5337 | 0.024* | |
C11 | 0.33668 (15) | 0.29919 (17) | 0.3361 (3) | 0.0220 (5) | |
C12 | 0.37305 (16) | 0.23303 (18) | 0.2384 (3) | 0.0284 (5) | |
H12 | 0.3401 | 0.2148 | 0.1478 | 0.034* | |
C13 | 0.45923 (18) | 0.19441 (17) | 0.2774 (3) | 0.0296 (6) | |
H13 | 0.4864 | 0.1485 | 0.2129 | 0.035* | |
C14 | 0.50657 (16) | 0.22190 (16) | 0.4100 (3) | 0.0234 (5) | |
H14 | 0.5657 | 0.1944 | 0.4350 | 0.028* | |
C15 | 0.56089 (15) | 0.48035 (14) | 0.5377 (3) | 0.0175 (4) | |
C18 | 0.76857 (15) | 0.43877 (16) | 0.5673 (3) | 0.0239 (5) | |
H18A | 0.8297 | 0.4088 | 0.5863 | 0.036* | 0.50 |
H18B | 0.7647 | 0.4957 | 0.6280 | 0.036* | 0.50 |
H18C | 0.7628 | 0.4535 | 0.4574 | 0.036* | 0.50 |
H18D | 0.7417 | 0.4966 | 0.5282 | 0.036* | 0.50 |
H18E | 0.8068 | 0.4096 | 0.4865 | 0.036* | 0.50 |
H18F | 0.8087 | 0.4518 | 0.6570 | 0.036* | 0.50 |
O4 | 0.28926 (15) | 0.5605 (3) | 0.6714 (4) | 0.0444 (10) | 0.886 (9) |
H4A | 0.3268 | 0.5401 | 0.7385 | 0.053* | 0.886 (9) |
C16 | 0.4424 (2) | 0.6052 (2) | 0.5703 (6) | 0.0290 (12) | 0.886 (9) |
H16A | 0.4717 | 0.6288 | 0.4743 | 0.035* | 0.886 (9) |
H16B | 0.4493 | 0.6536 | 0.6502 | 0.035* | 0.886 (9) |
C17 | 0.3408 (2) | 0.5896 (3) | 0.5422 (4) | 0.0317 (8) | 0.886 (9) |
H17A | 0.3124 | 0.6476 | 0.5034 | 0.038* | 0.886 (9) |
H17B | 0.3340 | 0.5426 | 0.4601 | 0.038* | 0.886 (9) |
O4' | 0.3123 (18) | 0.614 (2) | 0.735 (3) | 0.053 (7) | 0.114 (9) |
H4'A | 0.3444 | 0.5775 | 0.7887 | 0.064* | 0.114 (9) |
C16' | 0.4586 (14) | 0.6165 (11) | 0.591 (4) | 0.023 (5) | 0.114 (9) |
H16C | 0.4851 | 0.6393 | 0.4921 | 0.027* | 0.114 (9) |
H16D | 0.4805 | 0.6581 | 0.6740 | 0.027* | 0.114 (9) |
C17' | 0.3511 (14) | 0.619 (2) | 0.583 (3) | 0.045 (5) | 0.114 (9) |
H17C | 0.3302 | 0.6766 | 0.5319 | 0.054* | 0.114 (9) |
H17D | 0.3279 | 0.5662 | 0.5210 | 0.054* | 0.114 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0140 (7) | 0.0252 (8) | 0.0332 (9) | −0.0013 (6) | −0.0005 (7) | 0.0061 (7) |
O2 | 0.0183 (7) | 0.0172 (8) | 0.0389 (10) | −0.0022 (6) | −0.0007 (7) | 0.0098 (7) |
O3 | 0.0235 (7) | 0.0223 (8) | 0.0173 (7) | 0.0003 (6) | 0.0006 (6) | 0.0032 (7) |
O5 | 0.0239 (8) | 0.0368 (11) | 0.0616 (14) | 0.0111 (8) | −0.0143 (9) | −0.0038 (10) |
O6 | 0.0273 (10) | 0.0744 (16) | 0.0319 (10) | 0.0032 (9) | −0.0162 (9) | 0.0023 (10) |
N1 | 0.0125 (8) | 0.0191 (10) | 0.0257 (10) | 0.0006 (7) | −0.0029 (8) | 0.0045 (8) |
N2 | 0.0297 (10) | 0.0192 (10) | 0.0209 (10) | 0.0074 (8) | 0.0059 (9) | 0.0049 (8) |
N3 | 0.0202 (9) | 0.0328 (11) | 0.0329 (11) | 0.0001 (8) | −0.0052 (9) | 0.0110 (10) |
C1 | 0.0188 (10) | 0.0163 (10) | 0.0179 (9) | 0.0005 (8) | −0.0026 (9) | −0.0011 (8) |
C2 | 0.0168 (9) | 0.0155 (10) | 0.0170 (9) | 0.0005 (8) | −0.0013 (8) | −0.0009 (8) |
C3 | 0.0140 (9) | 0.0143 (10) | 0.0190 (11) | 0.0011 (7) | −0.0004 (8) | 0.0012 (8) |
C4 | 0.0168 (9) | 0.0168 (10) | 0.0170 (9) | −0.0008 (8) | −0.0013 (8) | 0.0007 (8) |
C5 | 0.0181 (9) | 0.0180 (10) | 0.0185 (10) | 0.0002 (8) | 0.0001 (8) | 0.0005 (9) |
C6 | 0.0182 (10) | 0.0194 (11) | 0.0270 (12) | 0.0028 (8) | −0.0037 (9) | 0.0040 (9) |
C7 | 0.0176 (10) | 0.0158 (10) | 0.0203 (10) | −0.0011 (8) | −0.0024 (9) | −0.0001 (8) |
C8 | 0.0273 (12) | 0.0197 (11) | 0.0368 (13) | −0.0076 (9) | −0.0016 (11) | 0.0071 (10) |
C9 | 0.0152 (10) | 0.0177 (10) | 0.0198 (10) | −0.0023 (8) | 0.0001 (8) | 0.0027 (8) |
C10 | 0.0173 (10) | 0.0169 (10) | 0.0246 (11) | −0.0004 (8) | −0.0009 (8) | 0.0044 (9) |
C11 | 0.0160 (10) | 0.0261 (12) | 0.0239 (11) | −0.0015 (8) | −0.0048 (9) | 0.0078 (9) |
C12 | 0.0260 (12) | 0.0360 (14) | 0.0231 (11) | −0.0057 (10) | −0.0063 (10) | −0.0016 (11) |
C13 | 0.0290 (12) | 0.0314 (13) | 0.0283 (13) | 0.0035 (10) | −0.0052 (10) | −0.0088 (11) |
C14 | 0.0186 (10) | 0.0258 (12) | 0.0258 (11) | 0.0022 (9) | −0.0023 (10) | −0.0031 (10) |
C15 | 0.0161 (9) | 0.0166 (9) | 0.0199 (10) | −0.0034 (8) | −0.0018 (8) | −0.0011 (9) |
C18 | 0.0196 (10) | 0.0224 (11) | 0.0297 (12) | −0.0045 (9) | −0.0012 (9) | 0.0048 (10) |
O4 | 0.0237 (11) | 0.062 (2) | 0.0480 (17) | −0.0023 (12) | −0.0012 (11) | 0.0304 (16) |
C16 | 0.0305 (16) | 0.0165 (14) | 0.040 (3) | 0.0078 (13) | 0.0093 (19) | 0.0112 (17) |
C17 | 0.0408 (17) | 0.0236 (16) | 0.0308 (16) | 0.0074 (13) | −0.0039 (13) | 0.0019 (14) |
O4' | 0.048 (11) | 0.072 (14) | 0.039 (11) | 0.027 (11) | 0.012 (9) | 0.026 (10) |
C16' | 0.022 (8) | 0.024 (9) | 0.021 (8) | 0.003 (7) | −0.009 (8) | −0.016 (7) |
C17' | 0.048 (8) | 0.038 (8) | 0.050 (8) | 0.008 (7) | 0.002 (7) | 0.007 (7) |
O1—C7 | 1.225 (2) | C9—C10 | 1.387 (3) |
O2—C7 | 1.344 (3) | C9—C14 | 1.395 (3) |
O2—C8 | 1.447 (3) | C10—C11 | 1.391 (3) |
O3—C15 | 1.248 (3) | C10—H10 | 0.9500 |
O5—N3 | 1.228 (3) | C11—C12 | 1.379 (4) |
O6—N3 | 1.221 (3) | C12—C13 | 1.380 (3) |
N1—C1 | 1.368 (3) | C12—H12 | 0.9500 |
N1—C5 | 1.391 (3) | C13—C14 | 1.387 (3) |
N1—H1 | 0.87 (3) | C13—H13 | 0.9500 |
N2—C15 | 1.335 (3) | C14—H14 | 0.9500 |
N2—C16 | 1.464 (3) | C18—H18A | 0.9800 |
N2—C16' | 1.468 (11) | C18—H18B | 0.9800 |
N2—H2 | 0.87 (3) | C18—H18C | 0.9800 |
N3—C11 | 1.470 (3) | C18—H18D | 0.9800 |
C1—C2 | 1.365 (3) | C18—H18E | 0.9800 |
C1—C6 | 1.504 (3) | C18—H18F | 0.9800 |
C2—C7 | 1.459 (3) | O4—C17 | 1.400 (4) |
C2—C3 | 1.517 (3) | O4—H4A | 0.8400 |
C3—C4 | 1.528 (3) | C16—C17 | 1.471 (5) |
C3—C9 | 1.529 (3) | C16—H16A | 0.9900 |
C3—H3 | 1.0000 | C16—H16B | 0.9900 |
C4—C5 | 1.346 (3) | C17—H17A | 0.9900 |
C4—C15 | 1.488 (3) | C17—H17B | 0.9900 |
C5—C18 | 1.499 (3) | O4'—C17' | 1.432 (11) |
C6—H6A | 0.9800 | O4'—H4'A | 0.8400 |
C6—H6B | 0.9800 | C16'—C17' | 1.518 (10) |
C6—H6C | 0.9800 | C16'—H16C | 0.9900 |
C8—H8A | 0.9800 | C16'—H16D | 0.9900 |
C8—H8B | 0.9800 | C17'—H17C | 0.9900 |
C8—H8C | 0.9800 | C17'—H17D | 0.9900 |
C7—O2—C8 | 116.35 (17) | C13—C12—H12 | 121.4 |
C1—N1—C5 | 123.73 (18) | C12—C13—C14 | 120.7 (2) |
C1—N1—H1 | 112.6 (18) | C12—C13—H13 | 119.7 |
C5—N1—H1 | 121.8 (18) | C14—C13—H13 | 119.7 |
C15—N2—C16 | 124.7 (2) | C13—C14—C9 | 121.2 (2) |
C15—N2—C16' | 125.0 (11) | C13—C14—H14 | 119.4 |
C16—N2—C16' | 13.0 (14) | C9—C14—H14 | 119.4 |
C15—N2—H2 | 120.6 (19) | O3—C15—N2 | 121.9 (2) |
C16—N2—H2 | 114.7 (19) | O3—C15—C4 | 122.9 (2) |
C16'—N2—H2 | 112 (2) | N2—C15—C4 | 115.19 (19) |
O6—N3—O5 | 123.2 (2) | C5—C18—H18A | 109.5 |
O6—N3—C11 | 119.0 (2) | C5—C18—H18B | 109.5 |
O5—N3—C11 | 117.8 (2) | H18A—C18—H18B | 109.5 |
C2—C1—N1 | 119.53 (19) | C5—C18—H18C | 109.5 |
C2—C1—C6 | 127.4 (2) | H18A—C18—H18C | 109.5 |
N1—C1—C6 | 113.11 (18) | H18B—C18—H18C | 109.5 |
C1—C2—C7 | 124.89 (19) | C5—C18—H18D | 109.5 |
C1—C2—C3 | 122.16 (18) | H18A—C18—H18D | 141.1 |
C7—C2—C3 | 112.94 (17) | H18B—C18—H18D | 56.3 |
C2—C3—C4 | 111.51 (16) | H18C—C18—H18D | 56.3 |
C2—C3—C9 | 112.06 (17) | C5—C18—H18E | 109.5 |
C4—C3—C9 | 108.56 (16) | H18A—C18—H18E | 56.3 |
C2—C3—H3 | 108.2 | H18B—C18—H18E | 141.1 |
C4—C3—H3 | 108.2 | H18C—C18—H18E | 56.3 |
C9—C3—H3 | 108.2 | H18D—C18—H18E | 109.5 |
C5—C4—C15 | 120.73 (19) | C5—C18—H18F | 109.5 |
C5—C4—C3 | 121.77 (19) | H18A—C18—H18F | 56.3 |
C15—C4—C3 | 117.39 (16) | H18B—C18—H18F | 56.3 |
C4—C5—N1 | 120.0 (2) | H18C—C18—H18F | 141.1 |
C4—C5—C18 | 126.6 (2) | H18D—C18—H18F | 109.5 |
N1—C5—C18 | 113.43 (18) | H18E—C18—H18F | 109.5 |
C1—C6—H6A | 109.5 | C17—O4—H4A | 109.5 |
C1—C6—H6B | 109.5 | N2—C16—C17 | 114.1 (3) |
H6A—C6—H6B | 109.5 | N2—C16—H16A | 108.7 |
C1—C6—H6C | 109.5 | C17—C16—H16A | 108.7 |
H6A—C6—H6C | 109.5 | N2—C16—H16B | 108.7 |
H6B—C6—H6C | 109.5 | C17—C16—H16B | 108.7 |
O1—C7—O2 | 121.20 (19) | H16A—C16—H16B | 107.6 |
O1—C7—C2 | 122.6 (2) | O4—C17—C16 | 114.8 (3) |
O2—C7—C2 | 116.22 (18) | O4—C17—H17A | 108.6 |
O2—C8—H8A | 109.5 | C16—C17—H17A | 108.6 |
O2—C8—H8B | 109.5 | O4—C17—H17B | 108.6 |
H8A—C8—H8B | 109.5 | C16—C17—H17B | 108.6 |
O2—C8—H8C | 109.5 | H17A—C17—H17B | 107.5 |
H8A—C8—H8C | 109.5 | C17'—O4'—H4'A | 109.5 |
H8B—C8—H8C | 109.5 | N2—C16'—C17' | 111.6 (11) |
C10—C9—C14 | 118.8 (2) | N2—C16'—H16C | 109.3 |
C10—C9—C3 | 120.3 (2) | C17'—C16'—H16C | 109.3 |
C14—C9—C3 | 120.95 (19) | N2—C16'—H16D | 109.3 |
C9—C10—C11 | 118.5 (2) | C17'—C16'—H16D | 109.3 |
C9—C10—H10 | 120.8 | H16C—C16'—H16D | 108.0 |
C11—C10—H10 | 120.8 | O4'—C17'—C16' | 109.8 (11) |
C12—C11—C10 | 123.5 (2) | O4'—C17'—H17C | 109.7 |
C12—C11—N3 | 119.0 (2) | C16'—C17'—H17C | 109.7 |
C10—C11—N3 | 117.5 (2) | O4'—C17'—H17D | 109.7 |
C11—C12—C13 | 117.3 (2) | C16'—C17'—H17D | 109.7 |
C11—C12—H12 | 121.4 | H17C—C17'—H17D | 108.2 |
C5—N1—C1—C2 | 6.7 (3) | C4—C3—C9—C14 | 82.3 (2) |
C5—N1—C1—C6 | −173.4 (2) | C14—C9—C10—C11 | −0.2 (3) |
N1—C1—C2—C7 | −178.3 (2) | C3—C9—C10—C11 | 178.97 (19) |
C6—C1—C2—C7 | 1.8 (4) | C9—C10—C11—C12 | −0.1 (3) |
N1—C1—C2—C3 | 2.9 (3) | C9—C10—C11—N3 | 178.1 (2) |
C6—C1—C2—C3 | −177.0 (2) | O6—N3—C11—C12 | 2.4 (3) |
C1—C2—C3—C4 | −11.0 (3) | O5—N3—C11—C12 | −178.9 (2) |
C7—C2—C3—C4 | 170.04 (18) | O6—N3—C11—C10 | −175.9 (2) |
C1—C2—C3—C9 | 110.9 (2) | O5—N3—C11—C10 | 2.8 (3) |
C7—C2—C3—C9 | −68.0 (2) | C10—C11—C12—C13 | 0.2 (4) |
C2—C3—C4—C5 | 11.2 (3) | N3—C11—C12—C13 | −177.9 (2) |
C9—C3—C4—C5 | −112.7 (2) | C11—C12—C13—C14 | −0.1 (4) |
C2—C3—C4—C15 | −172.45 (18) | C12—C13—C14—C9 | −0.2 (4) |
C9—C3—C4—C15 | 63.6 (2) | C10—C9—C14—C13 | 0.3 (3) |
C15—C4—C5—N1 | −179.6 (2) | C3—C9—C14—C13 | −178.8 (2) |
C3—C4—C5—N1 | −3.4 (3) | C16—N2—C15—O3 | 4.7 (4) |
C15—C4—C5—C18 | 2.2 (4) | C16'—N2—C15—O3 | −11.2 (17) |
C3—C4—C5—C18 | 178.4 (2) | C16—N2—C15—C4 | −173.7 (3) |
C1—N1—C5—C4 | −6.4 (3) | C16'—N2—C15—C4 | 170.4 (17) |
C1—N1—C5—C18 | 172.0 (2) | C5—C4—C15—O3 | 48.9 (3) |
C8—O2—C7—O1 | 4.8 (3) | C3—C4—C15—O3 | −127.5 (2) |
C8—O2—C7—C2 | −175.0 (2) | C5—C4—C15—N2 | −132.8 (2) |
C1—C2—C7—O1 | 176.8 (2) | C3—C4—C15—N2 | 50.9 (3) |
C3—C2—C7—O1 | −4.3 (3) | C15—N2—C16—C17 | 113.3 (4) |
C1—C2—C7—O2 | −3.4 (3) | C16'—N2—C16—C17 | −151 (5) |
C3—C2—C7—O2 | 175.53 (19) | N2—C16—C17—O4 | 61.5 (5) |
C2—C3—C9—C10 | 139.5 (2) | C15—N2—C16'—C17' | 129.2 (14) |
C4—C3—C9—C10 | −96.9 (2) | C16—N2—C16'—C17' | 36 (4) |
C2—C3—C9—C14 | −41.3 (3) | N2—C16'—C17'—O4' | 77 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···O3i | 0.84 | 2.05 | 2.892 (3) | 176 |
O4′—H4′A···O3i | 0.84 | 1.92 | 2.76 (2) | 176 |
N1—H1···O1ii | 0.87 (3) | 2.10 (3) | 2.920 (2) | 157 (2) |
N2—H2···O3i | 0.87 (3) | 2.00 (3) | 2.836 (3) | 161 (3) |
Symmetry codes: (i) −x+1, −y+1, z+1/2; (ii) x+1/2, −y+1/2, z. |
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