



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015013286/wm5184sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989015013286/wm5184Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015013286/wm5184Isup3.cml |
CCDC reference: 1412105
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.040
- wR factor = 0.120
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 2.636 Check
Alert level G PLAT154_ALERT_1_G The su's on the Cell Angles are Equal .......... 0.00400 Degree PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT793_ALERT_4_G The Model has Chirality at C5 (Centro SPGR) R Verify PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2014 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 61 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The synthesis of the title compound was described previously (Saidov et al., 2014). Orange crystals were obtained in a methanol:chloroform 1:1 (v/v) mixture by slow evaporation of the solvent at room temperature.
Carbon-bound H atoms were placed geometrically and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic), 0.97 Å (methylen) or 0.96 Å (methyl) and were refined with Uiso(H) = 1.2Ueq(C) for aromatic and methylene hydrogens and Uiso(H) = 1.5Ueq(C) for methyl H atoms. The N- and O-bound H atoms were located in a difference Fourier map and were refined freely.
Synthetic details regarding the title compound were described by Saidov et al. (2014). For synthetic procedures of related compounds and their structures, see: Saidov et al. (2013). For another related crystal structure, see: Yu et al. (1995).
The synthesis of the title compound was described previously (Saidov et al., 2014). Orange crystals were obtained in a methanol:chloroform 1:1 (v/v) mixture by slow evaporation of the solvent at room temperature.
Carbon-bound H atoms were placed geometrically and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic), 0.97 Å (methylen) or 0.96 Å (methyl) and were refined with Uiso(H) = 1.2Ueq(C) for aromatic and methylene hydrogens and Uiso(H) = 1.5Ueq(C) for methyl H atoms. The N- and O-bound H atoms were located in a difference Fourier map and were refined freely.
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
C21H22N2O2·CH4O | Z = 2 |
Mr = 366.45 | F(000) = 392 |
Triclinic, P1 | Dx = 1.273 Mg m−3 |
Hall symbol: -P 1 | Melting point: 393(2) K |
a = 7.6080 (3) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 11.8061 (5) Å | Cell parameters from 7310 reflections |
c = 12.3327 (5) Å | θ = 4.0–75.6° |
α = 65.242 (4)° | µ = 0.68 mm−1 |
β = 73.956 (4)° | T = 293 K |
γ = 75.724 (4)° | Prism, orange |
V = 955.81 (7) Å3 | 0.42 × 0.25 × 0.12 mm |
Oxford Diffraction Xcalibur Ruby diffractometer | 3936 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 2889 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
Detector resolution: 10.2576 pixels mm-1 | θmax = 75.8°, θmin = 4.0° |
ω scans | h = −9→8 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | k = −14→14 |
Tmin = 0.843, Tmax = 1.000 | l = −15→15 |
19864 measured reflections |
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)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.069P)2 + 0.0547P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.002 |
3936 reflections | Δρmax = 0.17 e Å−3 |
256 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0025 (6) |
C21H22N2O2·CH4O | γ = 75.724 (4)° |
Mr = 366.45 | V = 955.81 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.6080 (3) Å | Cu Kα radiation |
b = 11.8061 (5) Å | µ = 0.68 mm−1 |
c = 12.3327 (5) Å | T = 293 K |
α = 65.242 (4)° | 0.42 × 0.25 × 0.12 mm |
β = 73.956 (4)° |
Oxford Diffraction Xcalibur Ruby diffractometer | 3936 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | 2889 reflections with I > 2σ(I) |
Tmin = 0.843, Tmax = 1.000 | Rint = 0.046 |
19864 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.120 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.17 e Å−3 |
3936 reflections | Δρmin = −0.17 e Å−3 |
256 parameters |
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 | ||
O1 | 0.58933 (14) | 0.05796 (10) | 1.11979 (9) | 0.0544 (3) | |
O2 | 0.27998 (15) | 0.08093 (10) | 1.27098 (9) | 0.0582 (3) | |
O3 | 0.10908 (17) | 0.72865 (11) | 0.27339 (11) | 0.0653 (3) | |
N1 | 0.30388 (18) | 0.48439 (12) | 0.39691 (11) | 0.0499 (3) | |
N4 | 0.13746 (15) | 0.41753 (10) | 0.72574 (10) | 0.0430 (3) | |
C2 | 0.2862 (2) | 0.43976 (13) | 0.52151 (13) | 0.0457 (3) | |
C3 | 0.1738 (2) | 0.50958 (13) | 0.59986 (12) | 0.0462 (3) | |
H3A | 0.2404 | 0.5723 | 0.5951 | 0.055* | |
H3B | 0.0581 | 0.5523 | 0.5730 | 0.055* | |
C5 | 0.31440 (18) | 0.34322 (13) | 0.76212 (12) | 0.0437 (3) | |
H5A | 0.4035 | 0.4020 | 0.7338 | 0.052* | |
C6 | 0.3879 (2) | 0.25152 (14) | 0.69509 (13) | 0.0497 (3) | |
H6A | 0.5147 | 0.2147 | 0.7036 | 0.060* | |
H6B | 0.3139 | 0.1838 | 0.7305 | 0.060* | |
C7 | 0.37932 (19) | 0.32112 (14) | 0.56320 (13) | 0.0464 (3) | |
C8 | 0.45916 (19) | 0.28619 (14) | 0.45984 (13) | 0.0475 (3) | |
C9 | 0.5643 (2) | 0.17724 (16) | 0.44332 (16) | 0.0590 (4) | |
H9A | 0.5961 | 0.1063 | 0.5097 | 0.071* | |
C10 | 0.6200 (2) | 0.17645 (19) | 0.32772 (17) | 0.0669 (5) | |
H10A | 0.6895 | 0.1042 | 0.3163 | 0.080* | |
C11 | 0.5741 (2) | 0.28218 (19) | 0.22718 (16) | 0.0654 (5) | |
H11A | 0.6147 | 0.2792 | 0.1499 | 0.078* | |
C12 | 0.4700 (2) | 0.39083 (17) | 0.23980 (14) | 0.0578 (4) | |
H12A | 0.4405 | 0.4612 | 0.1724 | 0.069* | |
C13 | 0.4104 (2) | 0.39180 (15) | 0.35692 (13) | 0.0493 (3) | |
C14 | 0.0333 (2) | 0.48294 (13) | 0.80799 (13) | 0.0485 (3) | |
H14A | −0.0728 | 0.5392 | 0.7760 | 0.058* | |
H14B | 0.1113 | 0.5329 | 0.8141 | 0.058* | |
C15 | −0.0305 (2) | 0.38641 (14) | 0.93244 (13) | 0.0502 (4) | |
H15A | −0.0932 | 0.4286 | 0.9884 | 0.060* | |
H15B | −0.1174 | 0.3418 | 0.9273 | 0.060* | |
C16 | 0.29541 (19) | 0.27694 (13) | 0.89861 (12) | 0.0438 (3) | |
C17 | 0.13271 (19) | 0.29376 (13) | 0.97944 (13) | 0.0455 (3) | |
C18 | 0.1258 (2) | 0.22773 (14) | 1.10490 (13) | 0.0493 (3) | |
H18A | 0.0162 | 0.2376 | 1.1590 | 0.059* | |
C19 | 0.2769 (2) | 0.14886 (13) | 1.14984 (13) | 0.0473 (3) | |
C20 | 0.44399 (19) | 0.13467 (13) | 1.06780 (13) | 0.0452 (3) | |
C21 | 0.45059 (19) | 0.19815 (13) | 0.94490 (13) | 0.0456 (3) | |
H21A | 0.5607 | 0.1887 | 0.8909 | 0.055* | |
C22 | 0.7633 (2) | 0.04838 (16) | 1.04086 (15) | 0.0574 (4) | |
H22A | 0.8558 | −0.0020 | 1.0883 | 0.086* | |
H22B | 0.7961 | 0.1311 | 0.9928 | 0.086* | |
H22C | 0.7555 | 0.0096 | 0.9881 | 0.086* | |
C23 | 0.1439 (3) | 0.12453 (19) | 1.35495 (15) | 0.0724 (5) | |
H23A | 0.1714 | 0.0793 | 1.4350 | 0.109* | |
H23B | 0.0246 | 0.1109 | 1.3549 | 0.109* | |
H23C | 0.1433 | 0.2130 | 1.3319 | 0.109* | |
C24 | 0.0459 (3) | 0.81552 (19) | 0.3320 (2) | 0.0782 (5) | |
H24A | −0.0599 | 0.7900 | 0.3951 | 0.117* | |
H24B | 0.0122 | 0.8979 | 0.2737 | 0.117* | |
H24C | 0.1425 | 0.8178 | 0.3670 | 0.117* | |
H1A | 0.254 (2) | 0.5621 (17) | 0.3504 (15) | 0.060 (5)* | |
H3 | 0.014 (3) | 0.694 (2) | 0.2747 (18) | 0.085 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0513 (6) | 0.0577 (6) | 0.0479 (6) | 0.0017 (5) | −0.0120 (4) | −0.0179 (5) |
O2 | 0.0644 (7) | 0.0589 (6) | 0.0423 (6) | −0.0024 (5) | −0.0066 (5) | −0.0166 (5) |
O3 | 0.0602 (7) | 0.0617 (7) | 0.0753 (8) | −0.0148 (6) | −0.0117 (6) | −0.0251 (6) |
N1 | 0.0513 (7) | 0.0490 (7) | 0.0448 (7) | −0.0092 (6) | −0.0086 (5) | −0.0129 (6) |
N4 | 0.0425 (6) | 0.0410 (6) | 0.0441 (6) | −0.0033 (5) | −0.0078 (5) | −0.0168 (5) |
C2 | 0.0443 (8) | 0.0471 (7) | 0.0443 (7) | −0.0111 (6) | −0.0063 (6) | −0.0151 (6) |
C3 | 0.0470 (8) | 0.0412 (7) | 0.0476 (8) | −0.0066 (6) | −0.0094 (6) | −0.0141 (6) |
C5 | 0.0382 (7) | 0.0464 (7) | 0.0456 (7) | −0.0057 (6) | −0.0070 (6) | −0.0176 (6) |
C6 | 0.0483 (8) | 0.0512 (8) | 0.0455 (8) | 0.0031 (6) | −0.0102 (6) | −0.0195 (6) |
C7 | 0.0430 (8) | 0.0499 (8) | 0.0452 (7) | −0.0058 (6) | −0.0068 (6) | −0.0186 (6) |
C8 | 0.0409 (8) | 0.0554 (8) | 0.0490 (8) | −0.0098 (6) | −0.0074 (6) | −0.0217 (7) |
C9 | 0.0531 (9) | 0.0632 (10) | 0.0638 (10) | 0.0000 (7) | −0.0114 (7) | −0.0318 (8) |
C10 | 0.0594 (10) | 0.0801 (12) | 0.0719 (12) | −0.0031 (9) | −0.0079 (8) | −0.0462 (10) |
C11 | 0.0586 (10) | 0.0928 (13) | 0.0580 (10) | −0.0202 (9) | −0.0002 (8) | −0.0432 (10) |
C12 | 0.0548 (9) | 0.0743 (11) | 0.0481 (8) | −0.0198 (8) | −0.0061 (7) | −0.0238 (8) |
C13 | 0.0419 (8) | 0.0588 (9) | 0.0501 (8) | −0.0149 (6) | −0.0055 (6) | −0.0215 (7) |
C14 | 0.0467 (8) | 0.0461 (8) | 0.0540 (8) | −0.0009 (6) | −0.0090 (6) | −0.0240 (7) |
C15 | 0.0432 (8) | 0.0561 (8) | 0.0513 (8) | −0.0028 (6) | −0.0048 (6) | −0.0256 (7) |
C16 | 0.0422 (7) | 0.0452 (7) | 0.0456 (7) | −0.0079 (6) | −0.0063 (6) | −0.0194 (6) |
C17 | 0.0432 (8) | 0.0470 (7) | 0.0478 (8) | −0.0071 (6) | −0.0067 (6) | −0.0206 (6) |
C18 | 0.0466 (8) | 0.0526 (8) | 0.0470 (8) | −0.0082 (6) | −0.0010 (6) | −0.0219 (7) |
C19 | 0.0534 (9) | 0.0460 (7) | 0.0428 (7) | −0.0087 (6) | −0.0073 (6) | −0.0178 (6) |
C20 | 0.0466 (8) | 0.0438 (7) | 0.0481 (8) | −0.0045 (6) | −0.0115 (6) | −0.0201 (6) |
C21 | 0.0408 (7) | 0.0507 (8) | 0.0457 (8) | −0.0056 (6) | −0.0054 (6) | −0.0212 (6) |
C22 | 0.0457 (8) | 0.0602 (9) | 0.0602 (9) | −0.0036 (7) | −0.0108 (7) | −0.0192 (8) |
C23 | 0.0702 (12) | 0.0829 (12) | 0.0440 (9) | 0.0036 (9) | −0.0024 (8) | −0.0185 (9) |
C24 | 0.0810 (13) | 0.0703 (12) | 0.0934 (14) | −0.0119 (10) | −0.0234 (11) | −0.0362 (11) |
O1—C20 | 1.3658 (17) | C10—H10A | 0.9300 |
O1—C22 | 1.4207 (18) | C11—C12 | 1.376 (2) |
O2—C19 | 1.3720 (17) | C11—H11A | 0.9300 |
O2—C23 | 1.4143 (19) | C12—C13 | 1.393 (2) |
O3—C24 | 1.411 (2) | C12—H12A | 0.9300 |
O3—H3 | 0.91 (2) | C14—C15 | 1.512 (2) |
N1—C13 | 1.3743 (19) | C14—H14A | 0.9700 |
N1—C2 | 1.3782 (18) | C14—H14B | 0.9700 |
N1—H1A | 0.907 (18) | C15—C17 | 1.507 (2) |
N4—C14 | 1.4706 (17) | C15—H15A | 0.9700 |
N4—C3 | 1.4716 (17) | C15—H15B | 0.9700 |
N4—C5 | 1.4849 (17) | C16—C17 | 1.3885 (19) |
C2—C7 | 1.355 (2) | C16—C21 | 1.4040 (19) |
C2—C3 | 1.4856 (19) | C17—C18 | 1.403 (2) |
C3—H3A | 0.9700 | C18—C19 | 1.373 (2) |
C3—H3B | 0.9700 | C18—H18A | 0.9300 |
C5—C16 | 1.5115 (19) | C19—C20 | 1.412 (2) |
C5—C6 | 1.5374 (19) | C20—C21 | 1.3735 (19) |
C5—H5A | 0.9800 | C21—H21A | 0.9300 |
C6—C7 | 1.4959 (19) | C22—H22A | 0.9600 |
C6—H6A | 0.9700 | C22—H22B | 0.9600 |
C6—H6B | 0.9700 | C22—H22C | 0.9600 |
C7—C8 | 1.433 (2) | C23—H23A | 0.9600 |
C8—C9 | 1.399 (2) | C23—H23B | 0.9600 |
C8—C13 | 1.418 (2) | C23—H23C | 0.9600 |
C9—C10 | 1.374 (2) | C24—H24A | 0.9600 |
C9—H9A | 0.9300 | C24—H24B | 0.9600 |
C10—C11 | 1.395 (3) | C24—H24C | 0.9600 |
C20—O1—C22 | 117.34 (11) | C12—C13—C8 | 121.50 (15) |
C19—O2—C23 | 116.67 (12) | N4—C14—C15 | 109.21 (11) |
C24—O3—H3 | 111.0 (13) | N4—C14—H14A | 109.8 |
C13—N1—C2 | 108.22 (13) | C15—C14—H14A | 109.8 |
C13—N1—H1A | 126.7 (11) | N4—C14—H14B | 109.8 |
C2—N1—H1A | 125.0 (11) | C15—C14—H14B | 109.8 |
C14—N4—C3 | 109.92 (10) | H14A—C14—H14B | 108.3 |
C14—N4—C5 | 111.77 (11) | C17—C15—C14 | 110.14 (12) |
C3—N4—C5 | 109.95 (10) | C17—C15—H15A | 109.6 |
C7—C2—N1 | 110.50 (13) | C14—C15—H15A | 109.6 |
C7—C2—C3 | 124.68 (13) | C17—C15—H15B | 109.6 |
N1—C2—C3 | 124.76 (13) | C14—C15—H15B | 109.6 |
N4—C3—C2 | 107.82 (11) | H15A—C15—H15B | 108.1 |
N4—C3—H3A | 110.1 | C17—C16—C21 | 119.03 (13) |
C2—C3—H3A | 110.1 | C17—C16—C5 | 122.61 (13) |
N4—C3—H3B | 110.1 | C21—C16—C5 | 118.33 (12) |
C2—C3—H3B | 110.1 | C16—C17—C18 | 119.08 (13) |
H3A—C3—H3B | 108.5 | C16—C17—C15 | 120.00 (13) |
N4—C5—C16 | 112.57 (11) | C18—C17—C15 | 120.86 (12) |
N4—C5—C6 | 108.21 (11) | C19—C18—C17 | 121.73 (13) |
C16—C5—C6 | 112.62 (11) | C19—C18—H18A | 119.1 |
N4—C5—H5A | 107.7 | C17—C18—H18A | 119.1 |
C16—C5—H5A | 107.7 | O2—C19—C18 | 124.92 (13) |
C6—C5—H5A | 107.7 | O2—C19—C20 | 115.89 (13) |
C7—C6—C5 | 109.45 (12) | C18—C19—C20 | 119.19 (13) |
C7—C6—H6A | 109.8 | O1—C20—C21 | 125.15 (13) |
C5—C6—H6A | 109.8 | O1—C20—C19 | 115.63 (12) |
C7—C6—H6B | 109.8 | C21—C20—C19 | 119.21 (13) |
C5—C6—H6B | 109.8 | C20—C21—C16 | 121.71 (13) |
H6A—C6—H6B | 108.2 | C20—C21—H21A | 119.1 |
C2—C7—C8 | 106.95 (13) | C16—C21—H21A | 119.1 |
C2—C7—C6 | 121.66 (13) | O1—C22—H22A | 109.5 |
C8—C7—C6 | 131.38 (13) | O1—C22—H22B | 109.5 |
C9—C8—C13 | 118.97 (14) | H22A—C22—H22B | 109.5 |
C9—C8—C7 | 134.61 (15) | O1—C22—H22C | 109.5 |
C13—C8—C7 | 106.42 (13) | H22A—C22—H22C | 109.5 |
C10—C9—C8 | 119.10 (17) | H22B—C22—H22C | 109.5 |
C10—C9—H9A | 120.5 | O2—C23—H23A | 109.5 |
C8—C9—H9A | 120.5 | O2—C23—H23B | 109.5 |
C9—C10—C11 | 121.15 (17) | H23A—C23—H23B | 109.5 |
C9—C10—H10A | 119.4 | O2—C23—H23C | 109.5 |
C11—C10—H10A | 119.4 | H23A—C23—H23C | 109.5 |
C12—C11—C10 | 121.47 (16) | H23B—C23—H23C | 109.5 |
C12—C11—H11A | 119.3 | O3—C24—H24A | 109.5 |
C10—C11—H11A | 119.3 | O3—C24—H24B | 109.5 |
C11—C12—C13 | 117.78 (16) | H24A—C24—H24B | 109.5 |
C11—C12—H12A | 121.1 | O3—C24—H24C | 109.5 |
C13—C12—H12A | 121.1 | H24A—C24—H24C | 109.5 |
N1—C13—C12 | 130.61 (15) | H24B—C24—H24C | 109.5 |
N1—C13—C8 | 107.89 (13) | ||
C13—N1—C2—C7 | 0.40 (16) | C7—C8—C13—N1 | −1.05 (16) |
C13—N1—C2—C3 | −177.03 (13) | C9—C8—C13—C12 | −2.2 (2) |
C14—N4—C3—C2 | 177.49 (12) | C7—C8—C13—C12 | 178.47 (13) |
C5—N4—C3—C2 | 54.04 (14) | C3—N4—C14—C15 | 170.60 (11) |
C7—C2—C3—N4 | −16.43 (19) | C5—N4—C14—C15 | −67.03 (15) |
N1—C2—C3—N4 | 160.63 (13) | N4—C14—C15—C17 | 56.04 (16) |
C14—N4—C5—C16 | 39.91 (15) | N4—C5—C16—C17 | −5.02 (19) |
C3—N4—C5—C16 | 162.27 (11) | C6—C5—C16—C17 | −127.70 (15) |
C14—N4—C5—C6 | 165.02 (11) | N4—C5—C16—C21 | 176.81 (12) |
C3—N4—C5—C6 | −72.62 (13) | C6—C5—C16—C21 | 54.14 (17) |
N4—C5—C6—C7 | 47.51 (15) | C21—C16—C17—C18 | −2.5 (2) |
C16—C5—C6—C7 | 172.59 (11) | C5—C16—C17—C18 | 179.38 (13) |
N1—C2—C7—C8 | −1.06 (17) | C21—C16—C17—C15 | 174.74 (13) |
C3—C2—C7—C8 | 176.37 (13) | C5—C16—C17—C15 | −3.4 (2) |
N1—C2—C7—C6 | 178.11 (13) | C14—C15—C17—C16 | −21.95 (19) |
C3—C2—C7—C6 | −4.5 (2) | C14—C15—C17—C18 | 155.21 (13) |
C5—C6—C7—C2 | −11.52 (19) | C16—C17—C18—C19 | 1.3 (2) |
C5—C6—C7—C8 | 167.41 (14) | C15—C17—C18—C19 | −175.89 (14) |
C2—C7—C8—C9 | −177.88 (16) | C23—O2—C19—C18 | −21.5 (2) |
C6—C7—C8—C9 | 3.1 (3) | C23—O2—C19—C20 | 158.32 (15) |
C2—C7—C8—C13 | 1.28 (16) | C17—C18—C19—O2 | −179.63 (13) |
C6—C7—C8—C13 | −177.76 (14) | C17—C18—C19—C20 | 0.6 (2) |
C13—C8—C9—C10 | 1.1 (2) | C22—O1—C20—C21 | 3.5 (2) |
C7—C8—C9—C10 | −179.79 (16) | C22—O1—C20—C19 | −175.59 (13) |
C8—C9—C10—C11 | 0.2 (3) | O2—C19—C20—O1 | −1.91 (19) |
C9—C10—C11—C12 | −0.6 (3) | C18—C19—C20—O1 | 177.89 (12) |
C10—C11—C12—C13 | −0.4 (2) | O2—C19—C20—C21 | 178.95 (12) |
C2—N1—C13—C12 | −179.03 (15) | C18—C19—C20—C21 | −1.3 (2) |
C2—N1—C13—C8 | 0.44 (16) | O1—C20—C21—C16 | −179.02 (13) |
C11—C12—C13—N1 | −178.76 (15) | C19—C20—C21—C16 | 0.0 (2) |
C11—C12—C13—C8 | 1.8 (2) | C17—C16—C21—C20 | 1.8 (2) |
C9—C8—C13—N1 | 178.27 (13) | C5—C16—C21—C20 | −179.92 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O3 | 0.907 (19) | 1.982 (19) | 2.880 (2) | 170.1 (16) |
O3—H3···N4i | 0.91 (2) | 1.95 (2) | 2.840 (2) | 165 (2) |
Symmetry code: (i) −x, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O3 | 0.907 (19) | 1.982 (19) | 2.880 (2) | 170.1 (16) |
O3—H3···N4i | 0.91 (2) | 1.95 (2) | 2.840 (2) | 165 (2) |
Symmetry code: (i) −x, −y+1, −z+1. |