Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806055413/ez2058sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806055413/ez2058Isup2.hkl |
CCDC reference: 636253
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.010 Å
- R factor = 0.062
- wR factor = 0.180
- Data-to-parameter ratio = 7.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.57 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.83 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.18 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.21 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.60 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O4 - C27 .. 5.57 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C13 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C27 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
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 25.00 From the CIF: _reflns_number_total 2505 Count of symmetry unique reflns 2549 Completeness (_total/calc) 98.27% 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 PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C20 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000) and DIAMOND (Brandenburg, 2004); software used to prepare material for publication: SHELXTL.
C14H16N2O3 | Dx = 1.299 Mg m−3 |
Mr = 260.29 | Melting point: 475 K |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.516 (3) Å | Cell parameters from 1277 reflections |
b = 7.429 (2) Å | θ = 2.5–22.2° |
c = 16.101 (3) Å | µ = 0.09 mm−1 |
β = 104.878 (3)° | T = 298 K |
V = 1331.3 (6) Å3 | Needle, colourless |
Z = 4 | 0.52 × 0.11 × 0.08 mm |
F(000) = 552 |
Bruker SMART CCD area-detector diffractometer | 2505 independent reflections |
Radiation source: fine-focus sealed tube | 1614 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
φ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→10 |
Tmin = 0.954, Tmax = 0.993 | k = −8→8 |
6562 measured reflections | l = −17→19 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.062 | H-atom parameters constrained |
wR(F2) = 0.180 | w = 1/[σ2(Fo2) + (0.0758P)2 + 0.0608P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
2505 reflections | Δρmax = 0.35 e Å−3 |
331 parameters | Δρmin = −0.46 e Å−3 |
52 restraints | Absolute structure: Flack (1983), with how many Friedel pairs? |
Primary atom site location: structure-invariant direct methods |
Experimental. Spectroscopic analysis: 1H NMR (DMSO-d6, 360 MHz, δ, p.p.m.): 9.21 (br, 1H), 7.3 (br, 1H), 7.03–7.32 (m, 5H), 5.11 (s, 1H), 3.91 (q, 2H), 2.30 (s, 3H), 1.09 (t, 3H). Elemental analysis, calculated for C14H16N2O3: C 64.60, H 6.19, N 10.76%; found: C 64.25, H 6.21, N 10.68%. |
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 | ||
N1 | 0.9344 (4) | 0.6919 (7) | 0.1671 (3) | 0.0369 (12) | |
H1 | 0.9113 | 0.5908 | 0.1423 | 0.044* | |
N2 | 0.9317 (4) | 1.0012 (7) | 0.1613 (3) | 0.0393 (13) | |
H2 | 0.9386 | 1.0978 | 0.1335 | 0.047* | |
N3 | 0.8265 (4) | 0.4923 (7) | 0.9486 (3) | 0.0387 (12) | |
H3 | 0.8365 | 0.5925 | 0.9763 | 0.046* | |
N4 | 0.8286 (4) | 0.1844 (7) | 0.9499 (3) | 0.0346 (12) | |
H4 | 0.8657 | 0.0874 | 0.9707 | 0.042* | |
O1 | 1.0867 (4) | 1.0324 (7) | 0.4129 (2) | 0.0525 (12) | |
O2 | 1.1080 (5) | 0.7377 (8) | 0.4360 (3) | 0.0722 (16) | |
O3 | 0.8841 (3) | 0.8362 (6) | 0.0388 (2) | 0.0418 (10) | |
O4 | 0.6659 (4) | 0.1739 (7) | 0.6949 (2) | 0.0576 (13) | |
O5 | 0.6833 (4) | 0.4698 (7) | 0.6751 (3) | 0.0607 (14) | |
O6 | 0.9123 (3) | 0.3432 (6) | 1.0718 (2) | 0.0437 (10) | |
C1 | 1.0700 (6) | 0.8628 (10) | 0.3881 (4) | 0.0439 (15) | |
C2 | 0.9997 (5) | 0.8469 (9) | 0.2987 (3) | 0.0340 (13) | |
C3 | 0.9899 (5) | 0.6910 (9) | 0.2543 (3) | 0.0355 (14) | |
C4 | 1.0329 (6) | 0.5094 (9) | 0.2882 (4) | 0.0489 (17) | |
H4A | 1.0764 | 0.4547 | 0.2513 | 0.073* | |
H4B | 0.9652 | 0.4355 | 0.2900 | 0.073* | |
H4C | 1.0847 | 0.5212 | 0.3451 | 0.073* | |
C5 | 0.9142 (5) | 0.8461 (8) | 0.1180 (3) | 0.0321 (12) | |
C6 | 0.9399 (5) | 1.0170 (8) | 0.2532 (3) | 0.0354 (14) | |
H6 | 0.9914 | 1.1202 | 0.2758 | 0.042* | |
C7 | 0.8171 (5) | 1.0481 (8) | 0.2707 (3) | 0.0361 (14) | |
C8 | 0.7123 (6) | 0.9912 (12) | 0.2147 (5) | 0.068 (2) | |
H8 | 0.7151 | 0.9391 | 0.1627 | 0.082* | |
C9 | 0.6031 (7) | 1.0101 (13) | 0.2341 (6) | 0.082 (3) | |
H9 | 0.5334 | 0.9671 | 0.1963 | 0.099* | |
C10 | 0.5972 (7) | 1.0921 (11) | 0.3092 (5) | 0.068 (2) | |
H10 | 0.5236 | 1.1058 | 0.3222 | 0.082* | |
C11 | 0.6992 (6) | 1.1530 (12) | 0.3644 (4) | 0.061 (2) | |
H11 | 0.6953 | 1.2099 | 0.4150 | 0.073* | |
C12 | 0.8082 (6) | 1.1312 (10) | 0.3458 (4) | 0.0487 (18) | |
H12 | 0.8774 | 1.1731 | 0.3844 | 0.058* | |
C13 | 1.1584 (9) | 1.0611 (13) | 0.5007 (5) | 0.0903 (19) | |
H13A | 1.2321 | 0.9916 | 0.5112 | 0.108* | |
H13B | 1.1139 | 1.0223 | 0.5412 | 0.108* | |
C14 | 1.1865 (9) | 1.2542 (12) | 0.5121 (5) | 0.0903 (19) | |
H14A | 1.2327 | 1.2758 | 0.5700 | 0.135* | |
H14B | 1.1131 | 1.3220 | 0.5012 | 0.135* | |
H14C | 1.2319 | 1.2909 | 0.4727 | 0.135* | |
C15 | 0.6961 (5) | 0.3395 (11) | 0.7237 (4) | 0.0439 (15) | |
C16 | 0.7388 (5) | 0.3452 (9) | 0.8174 (3) | 0.0344 (13) | |
C17 | 0.7792 (5) | 0.4971 (9) | 0.8604 (3) | 0.0357 (15) | |
C18 | 0.7812 (6) | 0.6817 (9) | 0.8237 (4) | 0.0521 (18) | |
H18A | 0.7917 | 0.6727 | 0.7666 | 0.078* | |
H18B | 0.8464 | 0.7493 | 0.8591 | 0.078* | |
H18C | 0.7067 | 0.7416 | 0.8217 | 0.078* | |
C19 | 0.8580 (5) | 0.3378 (9) | 0.9935 (3) | 0.0321 (12) | |
C20 | 0.7360 (5) | 0.1734 (9) | 0.8683 (3) | 0.0348 (14) | |
H20 | 0.7563 | 0.0727 | 0.8354 | 0.042* | |
C21 | 0.6142 (5) | 0.1359 (8) | 0.8834 (4) | 0.0353 (14) | |
C22 | 0.5791 (6) | 0.2147 (11) | 0.9516 (4) | 0.0538 (19) | |
H22 | 0.6327 | 0.2868 | 0.9907 | 0.065* | |
C23 | 0.4647 (7) | 0.1858 (12) | 0.9613 (5) | 0.068 (2) | |
H23 | 0.4422 | 0.2400 | 1.0069 | 0.081* | |
C24 | 0.3844 (6) | 0.0800 (11) | 0.9059 (5) | 0.060 (2) | |
H24 | 0.3081 | 0.0615 | 0.9137 | 0.072* | |
C25 | 0.4170 (6) | 0.0002 (11) | 0.8378 (5) | 0.064 (2) | |
H25 | 0.3630 | −0.0728 | 0.7995 | 0.077* | |
C26 | 0.5312 (5) | 0.0299 (10) | 0.8273 (4) | 0.0513 (17) | |
H26 | 0.5525 | −0.0231 | 0.7810 | 0.062* | |
C27 | 0.6171 (9) | 0.1544 (15) | 0.6029 (5) | 0.101 (2) | |
H27A | 0.6819 | 0.1510 | 0.5746 | 0.121* | |
H27B | 0.5658 | 0.2561 | 0.5806 | 0.121* | |
C28 | 0.5477 (9) | −0.0128 (14) | 0.5861 (5) | 0.101 (2) | |
H28A | 0.5136 | −0.0255 | 0.5254 | 0.151* | |
H28B | 0.4845 | −0.0094 | 0.6150 | 0.151* | |
H28C | 0.5996 | −0.1132 | 0.6068 | 0.151* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.047 (3) | 0.025 (3) | 0.036 (3) | 0.000 (3) | 0.006 (2) | 0.005 (2) |
N2 | 0.055 (3) | 0.028 (3) | 0.038 (3) | −0.002 (3) | 0.016 (2) | −0.002 (3) |
N3 | 0.048 (3) | 0.030 (3) | 0.037 (3) | −0.002 (3) | 0.011 (2) | 0.000 (2) |
N4 | 0.032 (3) | 0.026 (3) | 0.039 (3) | 0.000 (2) | −0.002 (2) | −0.002 (2) |
O1 | 0.060 (3) | 0.051 (3) | 0.037 (2) | −0.002 (2) | −0.005 (2) | −0.015 (2) |
O2 | 0.101 (4) | 0.056 (4) | 0.047 (3) | 0.009 (3) | −0.004 (3) | 0.001 (3) |
O3 | 0.060 (3) | 0.035 (2) | 0.032 (2) | 0.006 (2) | 0.0160 (19) | 0.001 (2) |
O4 | 0.078 (3) | 0.057 (3) | 0.030 (2) | −0.017 (3) | 0.000 (2) | −0.007 (2) |
O5 | 0.076 (3) | 0.058 (3) | 0.045 (2) | 0.006 (3) | 0.009 (2) | 0.020 (3) |
O6 | 0.060 (3) | 0.037 (2) | 0.031 (2) | −0.004 (2) | 0.0070 (18) | −0.001 (2) |
C1 | 0.051 (4) | 0.039 (4) | 0.037 (3) | 0.003 (3) | 0.003 (3) | 0.004 (4) |
C2 | 0.040 (3) | 0.025 (3) | 0.036 (3) | 0.002 (3) | 0.007 (2) | 0.000 (3) |
C3 | 0.040 (3) | 0.034 (4) | 0.032 (3) | −0.001 (3) | 0.006 (2) | 0.007 (3) |
C4 | 0.069 (4) | 0.029 (4) | 0.046 (4) | 0.012 (3) | 0.009 (3) | 0.002 (3) |
C5 | 0.041 (3) | 0.018 (3) | 0.040 (3) | −0.002 (3) | 0.017 (2) | −0.001 (3) |
C6 | 0.048 (3) | 0.026 (3) | 0.033 (3) | 0.005 (3) | 0.013 (2) | 0.000 (3) |
C7 | 0.046 (3) | 0.025 (3) | 0.037 (3) | 0.002 (3) | 0.010 (3) | 0.002 (3) |
C8 | 0.043 (4) | 0.068 (6) | 0.093 (5) | 0.004 (4) | 0.015 (4) | −0.038 (5) |
C9 | 0.053 (5) | 0.078 (7) | 0.112 (7) | −0.008 (5) | 0.015 (5) | −0.047 (6) |
C10 | 0.058 (5) | 0.052 (5) | 0.101 (6) | −0.009 (4) | 0.033 (5) | −0.003 (5) |
C11 | 0.064 (5) | 0.066 (5) | 0.059 (4) | 0.004 (4) | 0.027 (4) | −0.013 (4) |
C12 | 0.047 (4) | 0.055 (5) | 0.044 (3) | 0.010 (3) | 0.012 (3) | −0.004 (3) |
C13 | 0.100 (4) | 0.079 (4) | 0.068 (3) | −0.005 (4) | −0.020 (3) | −0.021 (3) |
C14 | 0.100 (4) | 0.079 (4) | 0.068 (3) | −0.005 (4) | −0.020 (3) | −0.021 (3) |
C15 | 0.036 (3) | 0.051 (4) | 0.046 (3) | 0.007 (4) | 0.013 (3) | 0.008 (4) |
C16 | 0.035 (3) | 0.033 (4) | 0.038 (3) | 0.001 (3) | 0.013 (2) | 0.002 (3) |
C17 | 0.035 (3) | 0.035 (4) | 0.039 (3) | 0.004 (3) | 0.013 (3) | 0.007 (3) |
C18 | 0.059 (4) | 0.032 (4) | 0.061 (4) | 0.000 (4) | 0.008 (3) | 0.015 (3) |
C19 | 0.035 (3) | 0.028 (3) | 0.034 (3) | 0.000 (3) | 0.012 (2) | 0.000 (3) |
C20 | 0.037 (3) | 0.035 (4) | 0.031 (3) | 0.003 (3) | 0.005 (2) | −0.001 (3) |
C21 | 0.042 (3) | 0.022 (3) | 0.043 (3) | 0.000 (3) | 0.013 (3) | 0.007 (3) |
C22 | 0.042 (4) | 0.067 (5) | 0.058 (4) | −0.007 (4) | 0.022 (3) | −0.014 (4) |
C23 | 0.062 (5) | 0.073 (6) | 0.081 (5) | 0.006 (5) | 0.041 (4) | 0.007 (5) |
C24 | 0.039 (4) | 0.056 (5) | 0.089 (5) | −0.002 (4) | 0.027 (4) | 0.019 (4) |
C25 | 0.050 (4) | 0.067 (6) | 0.074 (5) | −0.021 (4) | 0.011 (4) | 0.001 (5) |
C26 | 0.051 (4) | 0.048 (4) | 0.056 (4) | −0.017 (4) | 0.014 (3) | −0.008 (4) |
C27 | 0.126 (5) | 0.101 (5) | 0.062 (3) | −0.028 (4) | 0.001 (3) | −0.017 (4) |
C28 | 0.126 (5) | 0.101 (5) | 0.062 (3) | −0.028 (4) | 0.001 (3) | −0.017 (4) |
N1—C5 | 1.377 (8) | C10—H10 | 0.9300 |
N1—C3 | 1.386 (7) | C11—C12 | 1.372 (9) |
N1—H1 | 0.8600 | C11—H11 | 0.9300 |
N2—C5 | 1.336 (8) | C12—H12 | 0.9300 |
N2—C6 | 1.463 (7) | C13—C14 | 1.472 (11) |
N2—H2 | 0.8600 | C13—H13A | 0.9700 |
N3—C19 | 1.355 (8) | C13—H13B | 0.9700 |
N3—C17 | 1.385 (7) | C14—H14A | 0.9600 |
N3—H3 | 0.8600 | C14—H14B | 0.9600 |
N4—C19 | 1.336 (8) | C14—H14C | 0.9600 |
N4—C20 | 1.466 (7) | C15—C16 | 1.462 (8) |
N4—H4 | 0.8600 | C16—C17 | 1.343 (9) |
O1—C1 | 1.320 (9) | C16—C20 | 1.522 (9) |
O1—C13 | 1.459 (8) | C17—C18 | 1.497 (9) |
O2—C1 | 1.215 (8) | C18—H18A | 0.9600 |
O3—C5 | 1.235 (6) | C18—H18B | 0.9600 |
O4—C15 | 1.330 (10) | C18—H18C | 0.9600 |
O4—C27 | 1.450 (8) | C20—C21 | 1.509 (8) |
O5—C15 | 1.230 (8) | C20—H20 | 0.9800 |
O6—C19 | 1.255 (6) | C21—C26 | 1.380 (8) |
C1—C2 | 1.464 (8) | C21—C22 | 1.394 (8) |
C2—C3 | 1.351 (9) | C22—C23 | 1.383 (9) |
C2—C6 | 1.532 (9) | C22—H22 | 0.9300 |
C3—C4 | 1.491 (9) | C23—C24 | 1.358 (11) |
C4—H4A | 0.9600 | C23—H23 | 0.9300 |
C4—H4B | 0.9600 | C24—C25 | 1.380 (10) |
C4—H4C | 0.9600 | C24—H24 | 0.9300 |
C6—C7 | 1.530 (8) | C25—C26 | 1.386 (9) |
C6—H6 | 0.9800 | C25—H25 | 0.9300 |
C7—C8 | 1.375 (8) | C26—H26 | 0.9300 |
C7—C12 | 1.384 (8) | C27—C28 | 1.464 (10) |
C8—C9 | 1.380 (10) | C27—H27A | 0.9700 |
C8—H8 | 0.9300 | C27—H27B | 0.9700 |
C9—C10 | 1.370 (10) | C28—H28A | 0.9600 |
C9—H9 | 0.9300 | C28—H28B | 0.9600 |
C10—C11 | 1.356 (10) | C28—H28C | 0.9600 |
C5—N1—C3 | 123.5 (5) | H13A—C13—H13B | 108.4 |
C5—N1—H1 | 118.2 | C13—C14—H14A | 109.5 |
C3—N1—H1 | 118.2 | C13—C14—H14B | 109.5 |
C5—N2—C6 | 124.0 (5) | H14A—C14—H14B | 109.5 |
C5—N2—H2 | 118.0 | C13—C14—H14C | 109.5 |
C6—N2—H2 | 118.0 | H14A—C14—H14C | 109.5 |
C19—N3—C17 | 123.3 (5) | H14B—C14—H14C | 109.5 |
C19—N3—H3 | 118.3 | O5—C15—O4 | 121.9 (5) |
C17—N3—H3 | 118.3 | O5—C15—C16 | 126.0 (7) |
C19—N4—C20 | 123.1 (5) | O4—C15—C16 | 112.1 (6) |
C19—N4—H4 | 118.5 | C17—C16—C15 | 122.5 (6) |
C20—N4—H4 | 118.5 | C17—C16—C20 | 118.6 (5) |
C1—O1—C13 | 115.7 (6) | C15—C16—C20 | 118.9 (6) |
C15—O4—C27 | 116.6 (6) | C16—C17—N3 | 120.0 (6) |
O2—C1—O1 | 122.5 (6) | C16—C17—C18 | 127.2 (5) |
O2—C1—C2 | 125.4 (7) | N3—C17—C18 | 112.8 (6) |
O1—C1—C2 | 112.0 (6) | C17—C18—H18A | 109.5 |
C3—C2—C1 | 122.6 (6) | C17—C18—H18B | 109.5 |
C3—C2—C6 | 119.2 (5) | H18A—C18—H18B | 109.5 |
C1—C2—C6 | 118.1 (6) | C17—C18—H18C | 109.5 |
C2—C3—N1 | 119.1 (6) | H18A—C18—H18C | 109.5 |
C2—C3—C4 | 127.4 (5) | H18B—C18—H18C | 109.5 |
N1—C3—C4 | 113.5 (5) | O6—C19—N4 | 123.3 (6) |
C3—C4—H4A | 109.5 | O6—C19—N3 | 120.3 (6) |
C3—C4—H4B | 109.5 | N4—C19—N3 | 116.4 (4) |
H4A—C4—H4B | 109.5 | N4—C20—C21 | 111.0 (4) |
C3—C4—H4C | 109.5 | N4—C20—C16 | 109.0 (5) |
H4A—C4—H4C | 109.5 | C21—C20—C16 | 113.0 (5) |
H4B—C4—H4C | 109.5 | N4—C20—H20 | 107.9 |
O3—C5—N2 | 123.7 (6) | C21—C20—H20 | 107.9 |
O3—C5—N1 | 120.3 (6) | C16—C20—H20 | 107.9 |
N2—C5—N1 | 116.0 (4) | C26—C21—C22 | 117.6 (6) |
N2—C6—C7 | 112.1 (5) | C26—C21—C20 | 121.1 (5) |
N2—C6—C2 | 108.8 (5) | C22—C21—C20 | 121.2 (5) |
C7—C6—C2 | 111.1 (5) | C23—C22—C21 | 120.1 (7) |
N2—C6—H6 | 108.3 | C23—C22—H22 | 119.9 |
C7—C6—H6 | 108.3 | C21—C22—H22 | 119.9 |
C2—C6—H6 | 108.3 | C24—C23—C22 | 121.5 (7) |
C8—C7—C12 | 117.5 (6) | C24—C23—H23 | 119.2 |
C8—C7—C6 | 122.0 (5) | C22—C23—H23 | 119.2 |
C12—C7—C6 | 120.5 (5) | C23—C24—C25 | 119.5 (6) |
C7—C8—C9 | 121.2 (7) | C23—C24—H24 | 120.2 |
C7—C8—H8 | 119.4 | C25—C24—H24 | 120.2 |
C9—C8—H8 | 119.4 | C24—C25—C26 | 119.3 (7) |
C10—C9—C8 | 120.0 (7) | C24—C25—H25 | 120.4 |
C10—C9—H9 | 120.0 | C26—C25—H25 | 120.4 |
C8—C9—H9 | 120.0 | C21—C26—C25 | 122.0 (6) |
C11—C10—C9 | 119.7 (7) | C21—C26—H26 | 119.0 |
C11—C10—H10 | 120.1 | C25—C26—H26 | 119.0 |
C9—C10—H10 | 120.1 | O4—C27—C28 | 108.9 (8) |
C10—C11—C12 | 120.3 (7) | O4—C27—H27A | 109.9 |
C10—C11—H11 | 119.8 | C28—C27—H27A | 109.9 |
C12—C11—H11 | 119.8 | O4—C27—H27B | 109.9 |
C11—C12—C7 | 121.3 (6) | C28—C27—H27B | 109.9 |
C11—C12—H12 | 119.3 | H27A—C27—H27B | 108.3 |
C7—C12—H12 | 119.3 | C27—C28—H28A | 109.5 |
O1—C13—C14 | 108.3 (8) | C27—C28—H28B | 109.5 |
O1—C13—H13A | 110.0 | H28A—C28—H28B | 109.5 |
C14—C13—H13A | 110.0 | C27—C28—H28C | 109.5 |
O1—C13—H13B | 110.0 | H28A—C28—H28C | 109.5 |
C14—C13—H13B | 110.0 | H28B—C28—H28C | 109.5 |
C13—O1—C1—O2 | 2.5 (10) | C27—O4—C15—O5 | 0.1 (9) |
C13—O1—C1—C2 | −178.7 (6) | C27—O4—C15—C16 | 177.3 (6) |
O2—C1—C2—C3 | −13.8 (10) | O5—C15—C16—C17 | −6.0 (9) |
O1—C1—C2—C3 | 167.3 (5) | O4—C15—C16—C17 | 177.0 (5) |
O2—C1—C2—C6 | 169.0 (6) | O5—C15—C16—C20 | 173.3 (6) |
O1—C1—C2—C6 | −9.8 (8) | O4—C15—C16—C20 | −3.8 (7) |
C1—C2—C3—N1 | −172.0 (5) | C15—C16—C17—N3 | −175.4 (5) |
C6—C2—C3—N1 | 5.1 (8) | C20—C16—C17—N3 | 5.4 (8) |
C1—C2—C3—C4 | 8.0 (10) | C15—C16—C17—C18 | 4.0 (9) |
C6—C2—C3—C4 | −174.9 (6) | C20—C16—C17—C18 | −175.3 (6) |
C5—N1—C3—C2 | 16.4 (8) | C19—N3—C17—C16 | 14.0 (8) |
C5—N1—C3—C4 | −163.6 (5) | C19—N3—C17—C18 | −165.4 (5) |
C6—N2—C5—O3 | 165.3 (5) | C20—N4—C19—O6 | 160.9 (5) |
C6—N2—C5—N1 | −16.2 (7) | C20—N4—C19—N3 | −19.5 (7) |
C3—N1—C5—O3 | 167.2 (5) | C17—N3—C19—O6 | 172.3 (5) |
C3—N1—C5—N2 | −11.4 (7) | C17—N3—C19—N4 | −7.4 (7) |
C5—N2—C6—C7 | −89.5 (7) | C19—N4—C20—C21 | −89.9 (6) |
C5—N2—C6—C2 | 33.7 (7) | C19—N4—C20—C16 | 35.2 (7) |
C3—C2—C6—N2 | −27.0 (8) | C17—C16—C20—N4 | −26.9 (7) |
C1—C2—C6—N2 | 150.2 (5) | C15—C16—C20—N4 | 153.8 (5) |
C3—C2—C6—C7 | 96.8 (6) | C17—C16—C20—C21 | 97.0 (6) |
C1—C2—C6—C7 | −85.9 (6) | C15—C16—C20—C21 | −82.2 (6) |
N2—C6—C7—C8 | 26.1 (9) | N4—C20—C21—C26 | −145.0 (6) |
C2—C6—C7—C8 | −95.9 (7) | C16—C20—C21—C26 | 92.2 (7) |
N2—C6—C7—C12 | −155.7 (6) | N4—C20—C21—C22 | 38.6 (8) |
C2—C6—C7—C12 | 82.3 (7) | C16—C20—C21—C22 | −84.2 (7) |
C12—C7—C8—C9 | −2.5 (12) | C26—C21—C22—C23 | 0.0 (10) |
C6—C7—C8—C9 | 175.8 (8) | C20—C21—C22—C23 | 176.5 (6) |
C7—C8—C9—C10 | 2.2 (14) | C21—C22—C23—C24 | 0.5 (12) |
C8—C9—C10—C11 | −0.5 (14) | C22—C23—C24—C25 | −0.4 (12) |
C9—C10—C11—C12 | −0.7 (13) | C23—C24—C25—C26 | −0.2 (12) |
C10—C11—C12—C7 | 0.4 (12) | C22—C21—C26—C25 | −0.6 (10) |
C8—C7—C12—C11 | 1.2 (11) | C20—C21—C26—C25 | −177.1 (6) |
C6—C7—C12—C11 | −177.1 (7) | C24—C25—C26—C21 | 0.7 (11) |
C1—O1—C13—C14 | 169.7 (8) | C15—O4—C27—C28 | −158.3 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O6i | 0.86 | 2.17 | 2.993 (7) | 161 |
N2—H2···O6ii | 0.86 | 2.07 | 2.907 (7) | 166 |
N3—H3···O3iii | 0.86 | 2.07 | 2.927 (7) | 172 |
N4—H4···O3iv | 0.86 | 2.15 | 2.947 (7) | 154 |
Symmetry codes: (i) x, y, z−1; (ii) x, y+1, z−1; (iii) x, y, z+1; (iv) x, y−1, z+1. |
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