The title compound, 2C
17H
13NO
2·C
3H
8O, adopts the keto–amine tautomeric form, with strong intramolecular N—H
O and intermolecular O—H
O hydrogen bonds which form an almost planar two-dimensional network. The asymmetric unit contains two molecules of the Schiff base and one propan-1-ol solvent molecule.
Supporting information
CCDC reference: 232179
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.047
- wR factor = 0.136
- Data-to-parameter ratio = 17.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for C21 - C22 = 8.22 su
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C2 = 6.05 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C5 = 5.16 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C18 - C19 = 6.84 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C23 - C24 = 5.27 su
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C35 - C36 = 1.38 Ang.
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C36 - C37 = 1.38 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3
C3 H8 O
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
7 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
1-[
N-(
p-Hydroxyphenyl)aminomethylidene]naphthalen-2(1
H)-one–propan-1-ol (2/1)
top
Crystal data top
2C17H13NO2·C3H8O | F(000) = 1240 |
Mr = 586.66 | Dx = 1.292 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 11900 reflections |
a = 17.2090 (17) Å | θ = 4.1–29.1° |
b = 8.9038 (6) Å | µ = 0.09 mm−1 |
c = 19.9334 (19) Å | T = 293 K |
β = 99.084 (8)° | Rectangular, orange |
V = 3016.0 (5) Å3 | 0.55 × 0.32 × 0.15 mm |
Z = 4 | |
Data collection top
Stoe IPDS-2 diffractometer | 3578 reflections with I > 2σ(I) |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | Rint = 0.053 |
Plane graphite monochromator | θmax = 27.5°, θmin = 2.1° |
Detector resolution: 6.67 pixels mm-1 | h = −21→22 |
rotation method scans | k = −11→11 |
24465 measured reflections | l = −25→25 |
6928 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.136 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.88 | w = 1/[σ2(Fo2) + (0.0779P)2] where P = (Fo2 + 2Fc2)/3 |
6928 reflections | (Δ/σ)max = 0.009 |
405 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.67533 (9) | 1.0193 (2) | 0.59055 (7) | 0.0526 (4) | |
C2 | 0.62399 (10) | 0.9100 (2) | 0.61182 (8) | 0.0583 (5) | |
C3 | 0.63343 (11) | 0.8714 (2) | 0.68231 (8) | 0.0685 (5) | |
H3 | 0.6002 | 0.8005 | 0.6971 | 0.082* | |
C4 | 0.68972 (11) | 0.9361 (2) | 0.72738 (8) | 0.0672 (5) | |
H4 | 0.6955 | 0.9059 | 0.7726 | 0.081* | |
C5 | 0.74084 (10) | 1.0489 (2) | 0.70887 (8) | 0.0569 (5) | |
C6 | 0.79758 (11) | 1.1171 (2) | 0.75801 (9) | 0.0674 (5) | |
H6 | 0.8023 | 1.0864 | 0.8031 | 0.081* | |
C7 | 0.84578 (12) | 1.2273 (3) | 0.74091 (10) | 0.0763 (6) | |
H7 | 0.8833 | 1.2711 | 0.7738 | 0.092* | |
C8 | 0.83793 (11) | 1.2730 (2) | 0.67360 (9) | 0.0716 (5) | |
H8 | 0.8699 | 1.3494 | 0.6616 | 0.086* | |
C9 | 0.78395 (10) | 1.2077 (2) | 0.62469 (9) | 0.0636 (5) | |
H9 | 0.7805 | 1.2396 | 0.5799 | 0.076* | |
C10 | 0.73342 (9) | 1.0931 (2) | 0.64045 (7) | 0.0533 (4) | |
C11 | 0.67082 (10) | 1.0504 (2) | 0.52124 (8) | 0.0550 (4) | |
H11 | 0.7062 | 1.1196 | 0.5083 | 0.066* | |
C12 | 0.61273 (9) | 1.0104 (2) | 0.40235 (7) | 0.0520 (4) | |
C13 | 0.65882 (10) | 1.1119 (2) | 0.37356 (8) | 0.0637 (5) | |
H13 | 0.6962 | 1.1696 | 0.4010 | 0.076* | |
C14 | 0.64889 (11) | 1.1266 (2) | 0.30405 (8) | 0.0685 (5) | |
H14 | 0.6795 | 1.1953 | 0.2847 | 0.082* | |
C15 | 0.59466 (10) | 1.0417 (2) | 0.26296 (8) | 0.0622 (5) | |
C16 | 0.54770 (10) | 0.9413 (2) | 0.29127 (8) | 0.0636 (5) | |
H16 | 0.5102 | 0.8842 | 0.2637 | 0.076* | |
C17 | 0.55729 (10) | 0.9271 (2) | 0.36117 (8) | 0.0599 (5) | |
H17 | 0.5258 | 0.8602 | 0.3806 | 0.072* | |
C18 | 0.16737 (10) | 0.2764 (2) | 0.34860 (8) | 0.0561 (4) | |
C19 | 0.12432 (10) | 0.1774 (2) | 0.38554 (9) | 0.0629 (5) | |
C20 | 0.06324 (11) | 0.0885 (2) | 0.34883 (10) | 0.0725 (5) | |
H20 | 0.0351 | 0.0231 | 0.3723 | 0.087* | |
C21 | 0.04556 (11) | 0.0972 (2) | 0.28097 (10) | 0.0743 (6) | |
H21 | 0.0053 | 0.0372 | 0.2587 | 0.089* | |
C22 | 0.08607 (10) | 0.1949 (2) | 0.24159 (9) | 0.0623 (5) | |
C23 | 0.06750 (12) | 0.1988 (3) | 0.17071 (10) | 0.0778 (6) | |
H23 | 0.0270 | 0.1384 | 0.1491 | 0.093* | |
C24 | 0.10748 (13) | 0.2893 (3) | 0.13253 (10) | 0.0833 (6) | |
H24 | 0.0944 | 0.2913 | 0.0855 | 0.100* | |
C25 | 0.16773 (12) | 0.3779 (3) | 0.16524 (9) | 0.0810 (6) | |
H25 | 0.1954 | 0.4397 | 0.1397 | 0.097* | |
C26 | 0.18750 (11) | 0.3763 (2) | 0.23452 (9) | 0.0712 (5) | |
H26 | 0.2283 | 0.4372 | 0.2552 | 0.085* | |
C27 | 0.14725 (10) | 0.2843 (2) | 0.27504 (8) | 0.0581 (4) | |
C28 | 0.23024 (10) | 0.3591 (2) | 0.38321 (8) | 0.0595 (5) | |
H28 | 0.2588 | 0.4204 | 0.3582 | 0.071* | |
C29 | 0.31331 (10) | 0.4311 (2) | 0.48966 (8) | 0.0549 (4) | |
C30 | 0.35871 (10) | 0.5387 (2) | 0.46429 (8) | 0.0565 (4) | |
H30 | 0.3486 | 0.5641 | 0.4185 | 0.068* | |
C31 | 0.41886 (10) | 0.6084 (2) | 0.50664 (7) | 0.0559 (4) | |
H31 | 0.4493 | 0.6805 | 0.4891 | 0.067* | |
C32 | 0.43452 (10) | 0.5725 (2) | 0.57472 (7) | 0.0547 (4) | |
C33 | 0.38919 (11) | 0.4661 (2) | 0.59993 (8) | 0.0671 (5) | |
H33 | 0.3993 | 0.4412 | 0.6458 | 0.081* | |
C34 | 0.32875 (11) | 0.3956 (2) | 0.55798 (8) | 0.0684 (5) | |
H34 | 0.2983 | 0.3241 | 0.5757 | 0.082* | |
C35 | 0.08239 (17) | −0.1658 (4) | 0.52328 (19) | 0.1467 (12) | |
H35A | 0.0538 | −0.0999 | 0.5495 | 0.176* | |
H35B | 0.0537 | −0.1684 | 0.4773 | 0.176* | |
C36 | 0.0816 (2) | −0.3090 (5) | 0.5503 (2) | 0.1750 (15) | |
H36A | 0.1002 | −0.3016 | 0.5987 | 0.210* | |
H36B | 0.0273 | −0.3420 | 0.5448 | 0.210* | |
C37 | 0.1244 (2) | −0.4203 (4) | 0.5249 (2) | 0.1963 (18) | |
H37A | 0.1216 | −0.5108 | 0.5506 | 0.294* | |
H37B | 0.1783 | −0.3892 | 0.5283 | 0.294* | |
H37C | 0.1031 | −0.4384 | 0.4782 | 0.294* | |
N1 | 0.61991 (9) | 0.98824 (18) | 0.47341 (6) | 0.0564 (4) | |
N2 | 0.25101 (9) | 0.35406 (18) | 0.44982 (7) | 0.0615 (4) | |
O1 | 0.57020 (7) | 0.84410 (15) | 0.56913 (5) | 0.0697 (4) | |
O2 | 0.58957 (8) | 1.06101 (18) | 0.19434 (5) | 0.0899 (5) | |
H22 | 0.5555 | 1.0052 | 0.1745 | 0.135* | |
O3 | 0.14070 (8) | 0.16518 (16) | 0.45084 (6) | 0.0796 (4) | |
O4 | 0.49403 (7) | 0.63595 (15) | 0.61821 (5) | 0.0679 (4) | |
H44 | 0.5169 | 0.6975 | 0.5977 | 0.102* | |
O5 | 0.15656 (9) | −0.10154 (18) | 0.52116 (7) | 0.0915 (4) | |
H55 | 0.1509 | −0.0173 | 0.5044 | 0.137* | |
H1 | 0.5862 (11) | 0.916 (2) | 0.4887 (9) | 0.088 (7)* | |
H2 | 0.2183 (11) | 0.281 (2) | 0.4685 (9) | 0.092 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0538 (10) | 0.0586 (12) | 0.0456 (9) | 0.0034 (9) | 0.0091 (8) | −0.0033 (8) |
C2 | 0.0556 (10) | 0.0706 (13) | 0.0486 (9) | 0.0016 (10) | 0.0079 (8) | −0.0091 (9) |
C3 | 0.0688 (12) | 0.0876 (15) | 0.0511 (10) | −0.0080 (11) | 0.0156 (9) | 0.0000 (10) |
C4 | 0.0696 (12) | 0.0906 (15) | 0.0419 (9) | 0.0080 (12) | 0.0107 (9) | −0.0023 (10) |
C5 | 0.0557 (10) | 0.0665 (13) | 0.0482 (9) | 0.0112 (10) | 0.0070 (8) | −0.0108 (9) |
C6 | 0.0672 (12) | 0.0832 (15) | 0.0499 (10) | 0.0132 (11) | 0.0033 (9) | −0.0125 (10) |
C7 | 0.0685 (13) | 0.0852 (16) | 0.0705 (13) | 0.0061 (12) | −0.0041 (10) | −0.0215 (11) |
C8 | 0.0657 (12) | 0.0714 (14) | 0.0746 (13) | −0.0021 (11) | 0.0009 (10) | −0.0117 (11) |
C9 | 0.0641 (11) | 0.0661 (13) | 0.0590 (10) | 0.0010 (10) | 0.0048 (9) | −0.0031 (10) |
C10 | 0.0532 (10) | 0.0585 (12) | 0.0478 (9) | 0.0100 (9) | 0.0064 (8) | −0.0082 (8) |
C11 | 0.0560 (10) | 0.0600 (12) | 0.0485 (9) | 0.0037 (9) | 0.0067 (8) | −0.0027 (8) |
C12 | 0.0528 (10) | 0.0596 (12) | 0.0425 (9) | 0.0013 (9) | 0.0046 (8) | −0.0013 (8) |
C13 | 0.0648 (11) | 0.0724 (13) | 0.0523 (10) | −0.0107 (10) | 0.0039 (8) | −0.0031 (9) |
C14 | 0.0721 (12) | 0.0796 (14) | 0.0540 (10) | −0.0191 (11) | 0.0102 (9) | 0.0032 (10) |
C15 | 0.0658 (11) | 0.0771 (14) | 0.0432 (9) | −0.0028 (10) | 0.0070 (8) | 0.0005 (9) |
C16 | 0.0605 (11) | 0.0769 (14) | 0.0511 (10) | −0.0094 (10) | 0.0023 (8) | −0.0080 (9) |
C17 | 0.0589 (10) | 0.0711 (13) | 0.0500 (9) | −0.0077 (10) | 0.0091 (8) | −0.0026 (9) |
C18 | 0.0566 (11) | 0.0522 (11) | 0.0602 (10) | −0.0004 (9) | 0.0114 (8) | −0.0044 (9) |
C19 | 0.0615 (11) | 0.0652 (13) | 0.0632 (11) | −0.0007 (10) | 0.0131 (9) | −0.0105 (10) |
C20 | 0.0637 (12) | 0.0740 (14) | 0.0828 (13) | −0.0102 (11) | 0.0208 (10) | −0.0082 (11) |
C21 | 0.0579 (11) | 0.0728 (15) | 0.0898 (14) | −0.0032 (11) | 0.0047 (10) | −0.0152 (12) |
C22 | 0.0554 (10) | 0.0592 (12) | 0.0703 (12) | 0.0046 (10) | 0.0032 (9) | −0.0064 (10) |
C23 | 0.0707 (13) | 0.0801 (15) | 0.0748 (13) | 0.0038 (12) | −0.0126 (10) | −0.0125 (12) |
C24 | 0.0943 (15) | 0.0890 (16) | 0.0602 (11) | 0.0039 (14) | −0.0072 (11) | 0.0032 (12) |
C25 | 0.0905 (15) | 0.0829 (16) | 0.0654 (12) | −0.0086 (13) | −0.0008 (11) | 0.0047 (11) |
C26 | 0.0786 (13) | 0.0704 (14) | 0.0615 (11) | −0.0080 (11) | 0.0015 (10) | −0.0008 (10) |
C27 | 0.0558 (10) | 0.0534 (11) | 0.0637 (11) | 0.0041 (9) | 0.0051 (9) | −0.0063 (9) |
C28 | 0.0627 (11) | 0.0577 (12) | 0.0584 (11) | 0.0005 (10) | 0.0110 (8) | −0.0044 (9) |
C29 | 0.0582 (10) | 0.0575 (12) | 0.0491 (9) | −0.0007 (9) | 0.0090 (8) | −0.0053 (9) |
C30 | 0.0618 (11) | 0.0630 (12) | 0.0447 (8) | 0.0020 (10) | 0.0088 (8) | 0.0033 (9) |
C31 | 0.0574 (10) | 0.0617 (12) | 0.0493 (9) | −0.0027 (9) | 0.0106 (8) | 0.0045 (9) |
C32 | 0.0557 (10) | 0.0624 (12) | 0.0459 (9) | −0.0013 (9) | 0.0079 (8) | 0.0010 (8) |
C33 | 0.0740 (12) | 0.0828 (15) | 0.0444 (9) | −0.0090 (11) | 0.0089 (9) | 0.0074 (9) |
C34 | 0.0781 (13) | 0.0749 (14) | 0.0539 (10) | −0.0138 (11) | 0.0156 (9) | 0.0082 (10) |
C35 | 0.113 (2) | 0.108 (3) | 0.239 (4) | 0.0142 (19) | 0.087 (2) | 0.038 (2) |
C36 | 0.174 (3) | 0.135 (3) | 0.239 (4) | 0.026 (3) | 0.107 (3) | 0.028 (3) |
C37 | 0.241 (4) | 0.104 (3) | 0.282 (5) | 0.034 (3) | 0.162 (4) | 0.030 (3) |
N1 | 0.0581 (9) | 0.0659 (11) | 0.0448 (8) | −0.0036 (8) | 0.0067 (7) | −0.0021 (7) |
N2 | 0.0671 (10) | 0.0650 (11) | 0.0530 (9) | −0.0077 (9) | 0.0115 (8) | −0.0054 (8) |
O1 | 0.0691 (8) | 0.0891 (10) | 0.0511 (6) | −0.0193 (7) | 0.0098 (6) | −0.0038 (6) |
O2 | 0.1062 (11) | 0.1173 (12) | 0.0453 (7) | −0.0290 (9) | 0.0088 (6) | 0.0045 (7) |
O3 | 0.0896 (9) | 0.0871 (11) | 0.0657 (8) | −0.0205 (8) | 0.0237 (7) | −0.0054 (7) |
O4 | 0.0675 (7) | 0.0861 (10) | 0.0483 (6) | −0.0126 (7) | 0.0031 (6) | 0.0042 (6) |
O5 | 0.0898 (10) | 0.0994 (12) | 0.0870 (9) | −0.0037 (9) | 0.0190 (8) | 0.0011 (8) |
Geometric parameters (Å, º) top
C1—C11 | 1.399 (2) | C21—H21 | 0.9300 |
C1—C2 | 1.423 (2) | C22—C23 | 1.399 (2) |
C1—C10 | 1.451 (2) | C22—C27 | 1.402 (2) |
C2—O1 | 1.2950 (19) | C23—C24 | 1.367 (3) |
C2—C3 | 1.431 (2) | C23—H23 | 0.9300 |
C3—C4 | 1.343 (2) | C24—C25 | 1.381 (3) |
C3—H3 | 0.9300 | C24—H24 | 0.9300 |
C4—C5 | 1.422 (3) | C25—C26 | 1.369 (2) |
C4—H4 | 0.9300 | C25—H25 | 0.9300 |
C5—C6 | 1.407 (2) | C26—C27 | 1.407 (2) |
C5—C10 | 1.406 (2) | C26—H26 | 0.9300 |
C6—C7 | 1.362 (3) | C28—N2 | 1.320 (2) |
C6—H6 | 0.9300 | C28—H28 | 0.9300 |
C7—C8 | 1.388 (3) | C29—C34 | 1.382 (2) |
C7—H7 | 0.9300 | C29—C30 | 1.382 (2) |
C8—C9 | 1.366 (2) | C29—N2 | 1.408 (2) |
C8—H8 | 0.9300 | C30—C31 | 1.376 (2) |
C9—C10 | 1.408 (2) | C30—H30 | 0.9300 |
C9—H9 | 0.9300 | C31—C32 | 1.379 (2) |
C11—N1 | 1.311 (2) | C31—H31 | 0.9300 |
C11—H11 | 0.9300 | C32—O4 | 1.3561 (18) |
C12—C17 | 1.374 (2) | C32—C33 | 1.372 (2) |
C12—C13 | 1.386 (2) | C33—C34 | 1.378 (2) |
C12—N1 | 1.416 (2) | C33—H33 | 0.9300 |
C13—C14 | 1.375 (2) | C34—H34 | 0.9300 |
C13—H13 | 0.9300 | C35—C36 | 1.385 (4) |
C14—C15 | 1.368 (2) | C35—O5 | 1.405 (3) |
C14—H14 | 0.9300 | C35—H35A | 0.9700 |
C15—O2 | 1.3676 (18) | C35—H35B | 0.9700 |
C15—C16 | 1.383 (2) | C36—C37 | 1.377 (4) |
C16—C17 | 1.383 (2) | C36—H36A | 0.9700 |
C16—H16 | 0.9300 | C36—H36B | 0.9700 |
C17—H17 | 0.9300 | C37—H37A | 0.9600 |
C18—C28 | 1.397 (2) | C37—H37B | 0.9600 |
C18—C19 | 1.429 (2) | C37—H37C | 0.9600 |
C18—C27 | 1.454 (2) | N1—H1 | 0.95 (2) |
C19—O3 | 1.292 (2) | N2—H2 | 0.97 (2) |
C19—C20 | 1.422 (2) | O2—H22 | 0.8200 |
C20—C21 | 1.341 (2) | O4—H44 | 0.8200 |
C20—H20 | 0.9300 | O5—H55 | 0.8200 |
C21—C22 | 1.425 (3) | | |
| | | |
C11—C1—C2 | 119.30 (15) | C27—C22—C21 | 118.72 (16) |
C11—C1—C10 | 120.79 (16) | C24—C23—C22 | 121.49 (19) |
C2—C1—C10 | 119.87 (14) | C24—C23—H23 | 119.3 |
O1—C2—C1 | 121.81 (14) | C22—C23—H23 | 119.3 |
O1—C2—C3 | 119.66 (17) | C23—C24—C25 | 118.69 (18) |
C1—C2—C3 | 118.53 (16) | C23—C24—H24 | 120.7 |
C4—C3—C2 | 120.79 (18) | C25—C24—H24 | 120.7 |
C4—C3—H3 | 119.6 | C26—C25—C24 | 121.2 (2) |
C2—C3—H3 | 119.6 | C26—C25—H25 | 119.4 |
C3—C4—C5 | 122.69 (16) | C24—C25—H25 | 119.4 |
C3—C4—H4 | 118.7 | C25—C26—C27 | 121.23 (19) |
C5—C4—H4 | 118.7 | C25—C26—H26 | 119.4 |
C6—C5—C10 | 120.08 (19) | C27—C26—H26 | 119.4 |
C6—C5—C4 | 120.94 (16) | C22—C27—C26 | 117.28 (16) |
C10—C5—C4 | 118.98 (16) | C22—C27—C18 | 119.57 (17) |
C7—C6—C5 | 121.32 (18) | C26—C27—C18 | 123.13 (16) |
C7—C6—H6 | 119.3 | N2—C28—C18 | 122.99 (17) |
C5—C6—H6 | 119.3 | N2—C28—H28 | 118.5 |
C6—C7—C8 | 118.87 (18) | C18—C28—H28 | 118.5 |
C6—C7—H7 | 120.6 | C34—C29—C30 | 119.14 (16) |
C8—C7—H7 | 120.6 | C34—C29—N2 | 117.10 (17) |
C9—C8—C7 | 121.1 (2) | C30—C29—N2 | 123.76 (15) |
C9—C8—H8 | 119.5 | C31—C30—C29 | 120.16 (15) |
C7—C8—H8 | 119.5 | C31—C30—H30 | 119.9 |
C8—C9—C10 | 121.59 (17) | C29—C30—H30 | 119.9 |
C8—C9—H9 | 119.2 | C30—C31—C32 | 120.70 (17) |
C10—C9—H9 | 119.2 | C30—C31—H31 | 119.6 |
C5—C10—C9 | 117.05 (16) | C32—C31—H31 | 119.6 |
C5—C10—C1 | 119.04 (17) | O4—C32—C33 | 117.98 (14) |
C9—C10—C1 | 123.92 (15) | O4—C32—C31 | 122.91 (16) |
N1—C11—C1 | 124.12 (17) | C33—C32—C31 | 119.10 (16) |
N1—C11—H11 | 117.9 | C32—C33—C34 | 120.69 (15) |
C1—C11—H11 | 117.9 | C32—C33—H33 | 119.7 |
C17—C12—C13 | 119.60 (14) | C34—C33—H33 | 119.7 |
C17—C12—N1 | 117.72 (16) | C33—C34—C29 | 120.21 (18) |
C13—C12—N1 | 122.67 (16) | C33—C34—H34 | 119.9 |
C14—C13—C12 | 119.41 (17) | C29—C34—H34 | 119.9 |
C14—C13—H13 | 120.3 | C36—C35—O5 | 116.8 (3) |
C12—C13—H13 | 120.3 | C36—C35—H35A | 108.1 |
C15—C14—C13 | 121.00 (18) | O5—C35—H35A | 108.1 |
C15—C14—H14 | 119.5 | C36—C35—H35B | 108.1 |
C13—C14—H14 | 119.5 | O5—C35—H35B | 108.1 |
O2—C15—C14 | 117.33 (17) | H35A—C35—H35B | 107.3 |
O2—C15—C16 | 122.68 (16) | C37—C36—C35 | 118.8 (3) |
C14—C15—C16 | 120.00 (15) | C37—C36—H36A | 107.6 |
C17—C16—C15 | 119.06 (17) | C35—C36—H36A | 107.6 |
C17—C16—H16 | 120.5 | C37—C36—H36B | 107.6 |
C15—C16—H16 | 120.5 | C35—C36—H36B | 107.6 |
C12—C17—C16 | 120.91 (17) | H36A—C36—H36B | 107.1 |
C12—C17—H17 | 119.5 | C36—C37—H37A | 109.5 |
C16—C17—H17 | 119.5 | C36—C37—H37B | 109.5 |
C28—C18—C19 | 119.65 (16) | H37A—C37—H37B | 109.5 |
C28—C18—C27 | 121.00 (17) | C36—C37—H37C | 109.5 |
C19—C18—C27 | 119.29 (16) | H37A—C37—H37C | 109.5 |
O3—C19—C20 | 119.82 (18) | H37B—C37—H37C | 109.5 |
O3—C19—C18 | 121.51 (16) | C11—N1—C12 | 127.69 (17) |
C20—C19—C18 | 118.65 (17) | C11—N1—H1 | 115.2 (11) |
C21—C20—C19 | 121.20 (19) | C12—N1—H1 | 117.0 (11) |
C21—C20—H20 | 119.4 | C28—N2—C29 | 127.75 (17) |
C19—C20—H20 | 119.4 | C28—N2—H2 | 109.0 (11) |
C20—C21—C22 | 122.56 (19) | C29—N2—H2 | 123.1 (11) |
C20—C21—H21 | 118.7 | C15—O2—H22 | 109.5 |
C22—C21—H21 | 118.7 | C32—O4—H44 | 109.5 |
C23—C22—C27 | 120.05 (19) | C35—O5—H55 | 109.5 |
C23—C22—C21 | 121.20 (18) | | |
| | | |
C11—C1—C2—O1 | −3.8 (3) | O3—C19—C20—C21 | −179.13 (18) |
C10—C1—C2—O1 | 178.43 (15) | C18—C19—C20—C21 | −0.4 (3) |
C11—C1—C2—C3 | 175.30 (16) | C19—C20—C21—C22 | −0.1 (3) |
C10—C1—C2—C3 | −2.5 (2) | C20—C21—C22—C23 | 178.44 (19) |
O1—C2—C3—C4 | 178.75 (17) | C20—C21—C22—C27 | 0.6 (3) |
C1—C2—C3—C4 | −0.3 (3) | C27—C22—C23—C24 | −0.5 (3) |
C2—C3—C4—C5 | 2.2 (3) | C21—C22—C23—C24 | −178.30 (19) |
C3—C4—C5—C6 | 178.10 (18) | C22—C23—C24—C25 | 0.4 (3) |
C3—C4—C5—C10 | −1.2 (3) | C23—C24—C25—C26 | −0.2 (3) |
C10—C5—C6—C7 | 0.5 (3) | C24—C25—C26—C27 | 0.1 (3) |
C4—C5—C6—C7 | −178.73 (18) | C23—C22—C27—C26 | 0.4 (3) |
C5—C6—C7—C8 | 0.4 (3) | C21—C22—C27—C26 | 178.25 (17) |
C6—C7—C8—C9 | −1.2 (3) | C23—C22—C27—C18 | −178.41 (17) |
C7—C8—C9—C10 | 0.9 (3) | C21—C22—C27—C18 | −0.5 (3) |
C6—C5—C10—C9 | −0.8 (2) | C25—C26—C27—C22 | −0.2 (3) |
C4—C5—C10—C9 | 178.49 (16) | C25—C26—C27—C18 | 178.54 (18) |
C6—C5—C10—C1 | 179.01 (16) | C28—C18—C27—C22 | 177.16 (16) |
C4—C5—C10—C1 | −1.7 (2) | C19—C18—C27—C22 | 0.0 (2) |
C8—C9—C10—C5 | 0.1 (2) | C28—C18—C27—C26 | −1.5 (3) |
C8—C9—C10—C1 | −179.69 (17) | C19—C18—C27—C26 | −178.69 (17) |
C11—C1—C10—C5 | −174.25 (16) | C19—C18—C28—N2 | −2.2 (3) |
C2—C1—C10—C5 | 3.5 (2) | C27—C18—C28—N2 | −179.31 (17) |
C11—C1—C10—C9 | 5.5 (3) | C34—C29—C30—C31 | 0.5 (3) |
C2—C1—C10—C9 | −176.70 (16) | N2—C29—C30—C31 | −179.71 (16) |
C2—C1—C11—N1 | 2.3 (3) | C29—C30—C31—C32 | −0.2 (3) |
C10—C1—C11—N1 | −179.95 (16) | C30—C31—C32—O4 | 178.71 (16) |
C17—C12—C13—C14 | −0.7 (3) | C30—C31—C32—C33 | −0.1 (3) |
N1—C12—C13—C14 | 179.56 (17) | O4—C32—C33—C34 | −178.83 (17) |
C12—C13—C14—C15 | −0.5 (3) | C31—C32—C33—C34 | 0.0 (3) |
C13—C14—C15—O2 | −178.72 (18) | C32—C33—C34—C29 | 0.3 (3) |
C13—C14—C15—C16 | 1.3 (3) | C30—C29—C34—C33 | −0.6 (3) |
O2—C15—C16—C17 | 179.13 (18) | N2—C29—C34—C33 | 179.64 (17) |
C14—C15—C16—C17 | −0.9 (3) | O5—C35—C36—C37 | −52.6 (6) |
C13—C12—C17—C16 | 1.1 (3) | C1—C11—N1—C12 | −178.22 (17) |
N1—C12—C17—C16 | −179.14 (16) | C17—C12—N1—C11 | 176.73 (17) |
C15—C16—C17—C12 | −0.3 (3) | C13—C12—N1—C11 | −3.5 (3) |
C28—C18—C19—O3 | 1.9 (3) | C18—C28—N2—C29 | 179.43 (17) |
C27—C18—C19—O3 | 179.14 (17) | C34—C29—N2—C28 | −173.34 (18) |
C28—C18—C19—C20 | −176.73 (17) | C30—C29—N2—C28 | 6.9 (3) |
C27—C18—C19—C20 | 0.5 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.95 (2) | 1.79 (2) | 2.556 (2) | 136 (2) |
N2—H2···O3 | 0.97 (2) | 1.68 (2) | 2.539 (2) | 145 (2) |
O2—H22···O4i | 0.82 | 1.89 | 2.701 (2) | 168 |
O4—H44···O1 | 0.82 | 1.74 | 2.552 (2) | 169 |
O5—H55···O3 | 0.82 | 1.94 | 2.749 (2) | 170 |
Symmetry code: (i) x, −y+3/2, z−1/2. |