The crystal structure of the title compound, C
16H
17NO
2, contains two independent molecules in the asymmetric unit. Both molecules adopt the phenol–imine tautomeric form, with strong intramolecular O—H
N hydrogen bonds. The crystal packing is stabilized by van der Waals interactions.
Supporting information
CCDC reference: 636728
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.002 Å
- R factor = 0.038
- wR factor = 0.116
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.75 mm
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 600 Deg.
PLAT230_ALERT_2_C Hirshfeld Test Diff for O1B - C1B .. 6.55 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for O2B - C12B .. 5.12 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C2B - C3B .. 6.22 su
PLAT355_ALERT_3_C Long O-H Bond (0.82A) O1A - H1A ... 1.06 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 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
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
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
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 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
(
E)-2-[1-(4-Ethoxyphenylimino)ethyl]phenol
top
Crystal data top
C16H17NO2 | Z = 4 |
Mr = 255.31 | F(000) = 544 |
Triclinic, P1 | Dx = 1.229 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0671 (7) Å | Cell parameters from 21129 reflections |
b = 11.1923 (8) Å | θ = 1.9–27.9° |
c = 14.8312 (12) Å | µ = 0.08 mm−1 |
α = 86.037 (6)° | T = 296 K |
β = 75.742 (6)° | Prism, green |
γ = 71.119 (6)° | 0.75 × 0.60 × 0.36 mm |
V = 1380.15 (18) Å3 | |
Data collection top
Stoe IPDS-2 diffractometer | 3807 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.042 |
Graphite monochromator | θmax = 27.9°, θmin = 1.9° |
Detector resolution: 6.67 pixels mm-1 | h = −11→11 |
ω scans | k = −14→14 |
22614 measured reflections | l = −19→19 |
6540 independent reflections | |
Refinement top
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)] = 0.038 | All H-atom parameters refined |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.0589P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
6540 reflections | Δρmax = 0.12 e Å−3 |
480 parameters | Δρmin = −0.11 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0189 (17) |
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 | |
H2A | 0.7904 (19) | 0.8443 (16) | 0.4806 (11) | 0.099 (5)* | |
H2B | 1.3045 (18) | 0.3804 (15) | 0.4939 (11) | 0.095 (5)* | |
H3A | 0.8555 (18) | 1.0344 (15) | 0.4892 (11) | 0.095 (5)* | |
H3B | 1.3709 (18) | 0.5698 (14) | 0.4975 (11) | 0.096 (5)* | |
H4A | 0.7574 (19) | 1.2111 (16) | 0.4087 (11) | 0.103 (5)* | |
H4B | 1.2644 (18) | 0.7444 (15) | 0.4055 (10) | 0.101 (5)* | |
H5A | 0.5728 (18) | 1.2108 (15) | 0.3200 (11) | 0.090 (5)* | |
H5B | 1.0895 (16) | 0.7261 (13) | 0.3181 (10) | 0.078 (4)* | |
H8A | 0.358 (2) | 1.1228 (15) | 0.1874 (12) | 0.102 (5)* | |
H8B | 0.502 (2) | 1.1648 (15) | 0.1974 (11) | 0.099 (5)* | |
H8C | 0.337 (2) | 1.2112 (19) | 0.2716 (13) | 0.126 (6)* | |
H8D | 0.8794 (19) | 0.6211 (14) | 0.1898 (11) | 0.096 (5)* | |
H8E | 1.027 (2) | 0.6654 (15) | 0.1933 (12) | 0.103 (5)* | |
H8F | 0.857 (2) | 0.7144 (19) | 0.2691 (13) | 0.128 (7)* | |
H10A | 0.1156 (15) | 1.0494 (12) | 0.3100 (9) | 0.071 (4)* | |
H10B | 0.6353 (17) | 0.5516 (14) | 0.3217 (10) | 0.089 (4)* | |
H11A | −0.0606 (18) | 1.0245 (13) | 0.2259 (10) | 0.082 (4)* | |
H11B | 0.4634 (18) | 0.5206 (13) | 0.2401 (10) | 0.082 (4)* | |
H13A | 0.3051 (15) | 0.7639 (13) | 0.0595 (9) | 0.074 (4)* | |
H13B | 0.8308 (14) | 0.2598 (11) | 0.0755 (8) | 0.062 (3)* | |
H14A | 0.4783 (16) | 0.7836 (12) | 0.1511 (9) | 0.071 (4)* | |
H14B | 1.0061 (17) | 0.2854 (13) | 0.1616 (9) | 0.081 (4)* | |
H15A | −0.1653 (17) | 1.0304 (15) | 0.0909 (10) | 0.087 (4)* | |
H15B | −0.1970 (16) | 0.9262 (12) | 0.1684 (10) | 0.075 (4)* | |
H15C | 0.3615 (17) | 0.5268 (15) | 0.1056 (10) | 0.083 (4)* | |
H15D | 0.3199 (16) | 0.4228 (13) | 0.1819 (10) | 0.079 (4)* | |
H16A | −0.341 (2) | 0.9391 (17) | 0.0483 (12) | 0.115 (6)* | |
H16B | −0.176 (2) | 0.9032 (16) | −0.0278 (13) | 0.115 (6)* | |
H16C | −0.2081 (18) | 0.7985 (17) | 0.0522 (11) | 0.098 (5)* | |
H16D | 0.187 (2) | 0.4433 (16) | 0.0552 (11) | 0.100 (5)* | |
H16E | 0.350 (2) | 0.4070 (15) | −0.0156 (13) | 0.104 (5)* | |
H16F | 0.311 (2) | 0.3030 (19) | 0.0581 (12) | 0.118 (6)* | |
H1B | 1.0495 (18) | 0.3449 (14) | 0.3720 (11) | 0.085 (4)* | |
H1A | 0.521 (2) | 0.8364 (19) | 0.3514 (15) | 0.143 (7)* | |
C1B | 1.16040 (14) | 0.44268 (11) | 0.40599 (8) | 0.0613 (3) | |
C2B | 1.26215 (16) | 0.45331 (16) | 0.45952 (9) | 0.0746 (4) | |
C3B | 1.29759 (17) | 0.56272 (15) | 0.46043 (10) | 0.0764 (4) | |
C4B | 1.23491 (17) | 0.66418 (15) | 0.40787 (9) | 0.0740 (4) | |
C5B | 1.13546 (16) | 0.65491 (13) | 0.35417 (9) | 0.0657 (3) | |
C6B | 1.09475 (13) | 0.54507 (10) | 0.35122 (7) | 0.0563 (3) | |
C7B | 0.98714 (14) | 0.53698 (11) | 0.29395 (7) | 0.0563 (3) | |
C8B | 0.9338 (2) | 0.64415 (14) | 0.23072 (11) | 0.0715 (4) | |
C9B | 0.83832 (15) | 0.42267 (10) | 0.24826 (8) | 0.0585 (3) | |
C10B | 0.67692 (16) | 0.49069 (12) | 0.27113 (9) | 0.0670 (3) | |
C11B | 0.57243 (16) | 0.47470 (12) | 0.22286 (9) | 0.0652 (3) | |
C12B | 0.63044 (14) | 0.38970 (10) | 0.14890 (8) | 0.0569 (3) | |
C13B | 0.79149 (15) | 0.31911 (12) | 0.12659 (9) | 0.0654 (3) | |
C14B | 0.89343 (16) | 0.33405 (12) | 0.17632 (9) | 0.0648 (3) | |
C15B | 0.37284 (16) | 0.43978 (14) | 0.11359 (10) | 0.0685 (3) | |
C16B | 0.3005 (2) | 0.39662 (19) | 0.04737 (12) | 0.0828 (4) | |
N1B | 0.94658 (12) | 0.43604 (9) | 0.29865 (7) | 0.0622 (3) | |
O1B | 1.12686 (13) | 0.33383 (9) | 0.40821 (7) | 0.0784 (3) | |
O2B | 0.53865 (10) | 0.36826 (8) | 0.09481 (6) | 0.0670 (2) | |
C1A | 0.64082 (14) | 0.92035 (12) | 0.39641 (8) | 0.0658 (3) | |
C2A | 0.74621 (18) | 0.92312 (17) | 0.44941 (10) | 0.0815 (4) | |
C3A | 0.78574 (19) | 1.03024 (19) | 0.45434 (11) | 0.0870 (5) | |
C4A | 0.7233 (2) | 1.13701 (18) | 0.40628 (11) | 0.0855 (4) | |
C5A | 0.62006 (18) | 1.13547 (14) | 0.35339 (9) | 0.0732 (4) | |
C6A | 0.57551 (14) | 1.02804 (11) | 0.34612 (8) | 0.0603 (3) | |
C7A | 0.46547 (14) | 1.02769 (11) | 0.28830 (8) | 0.0598 (3) | |
C8A | 0.4116 (2) | 1.14056 (14) | 0.22978 (12) | 0.0771 (4) | |
C9A | 0.31483 (15) | 0.91974 (11) | 0.23646 (8) | 0.0618 (3) | |
C10A | 0.15394 (16) | 0.98938 (13) | 0.25888 (9) | 0.0697 (3) | |
C11A | 0.04917 (17) | 0.97574 (12) | 0.20981 (9) | 0.0667 (3) | |
C12A | 0.10610 (15) | 0.89148 (11) | 0.13539 (8) | 0.0597 (3) | |
C13A | 0.26711 (16) | 0.81988 (12) | 0.11318 (9) | 0.0655 (3) | |
C14A | 0.36912 (17) | 0.83258 (12) | 0.16340 (9) | 0.0671 (3) | |
C15A | −0.15278 (16) | 0.93918 (14) | 0.10204 (10) | 0.0706 (3) | |
C16A | −0.2261 (2) | 0.89048 (19) | 0.03906 (13) | 0.0857 (4) | |
N1A | 0.42293 (12) | 0.92839 (9) | 0.28831 (7) | 0.0651 (3) | |
O1A | 0.60472 (12) | 0.81298 (9) | 0.39403 (7) | 0.0834 (3) | |
O2A | 0.01439 (10) | 0.87113 (8) | 0.08118 (6) | 0.0682 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1B | 0.0603 (7) | 0.0615 (7) | 0.0529 (6) | −0.0120 (6) | −0.0069 (5) | 0.0010 (5) |
C2B | 0.0665 (8) | 0.0862 (10) | 0.0605 (7) | −0.0085 (7) | −0.0176 (6) | 0.0033 (7) |
C3B | 0.0674 (8) | 0.0967 (11) | 0.0642 (8) | −0.0218 (8) | −0.0168 (7) | −0.0088 (7) |
C4B | 0.0760 (9) | 0.0825 (9) | 0.0660 (8) | −0.0296 (7) | −0.0127 (7) | −0.0088 (7) |
C5B | 0.0711 (8) | 0.0670 (8) | 0.0569 (7) | −0.0211 (6) | −0.0120 (6) | −0.0002 (6) |
C6B | 0.0558 (6) | 0.0602 (7) | 0.0453 (5) | −0.0129 (5) | −0.0055 (5) | −0.0007 (5) |
C7B | 0.0589 (7) | 0.0561 (6) | 0.0468 (6) | −0.0147 (5) | −0.0045 (5) | 0.0004 (5) |
C8B | 0.0816 (10) | 0.0684 (8) | 0.0695 (8) | −0.0270 (8) | −0.0269 (8) | 0.0161 (7) |
C9B | 0.0664 (7) | 0.0532 (6) | 0.0539 (6) | −0.0202 (6) | −0.0100 (5) | 0.0042 (5) |
C10B | 0.0686 (8) | 0.0688 (8) | 0.0581 (7) | −0.0182 (7) | −0.0063 (6) | −0.0120 (6) |
C11B | 0.0593 (7) | 0.0664 (7) | 0.0621 (7) | −0.0148 (6) | −0.0044 (6) | −0.0106 (6) |
C12B | 0.0634 (7) | 0.0540 (6) | 0.0539 (6) | −0.0241 (6) | −0.0077 (5) | −0.0002 (5) |
C13B | 0.0662 (8) | 0.0569 (7) | 0.0673 (7) | −0.0175 (6) | −0.0040 (6) | −0.0134 (6) |
C14B | 0.0599 (7) | 0.0568 (7) | 0.0715 (8) | −0.0140 (6) | −0.0087 (6) | −0.0061 (6) |
C15B | 0.0655 (8) | 0.0633 (8) | 0.0756 (9) | −0.0213 (7) | −0.0135 (7) | 0.0010 (6) |
C16B | 0.0799 (11) | 0.0954 (12) | 0.0800 (10) | −0.0358 (9) | −0.0221 (8) | 0.0063 (8) |
N1B | 0.0686 (6) | 0.0613 (6) | 0.0564 (5) | −0.0205 (5) | −0.0150 (5) | 0.0035 (4) |
O1B | 0.0873 (7) | 0.0662 (6) | 0.0816 (6) | −0.0191 (5) | −0.0313 (5) | 0.0161 (5) |
O2B | 0.0638 (5) | 0.0685 (5) | 0.0671 (5) | −0.0213 (4) | −0.0091 (4) | −0.0107 (4) |
C1A | 0.0577 (7) | 0.0694 (8) | 0.0562 (7) | −0.0101 (6) | −0.0025 (6) | 0.0036 (6) |
C2A | 0.0682 (9) | 0.0967 (11) | 0.0650 (8) | −0.0110 (8) | −0.0116 (7) | 0.0077 (8) |
C3A | 0.0712 (9) | 0.1206 (14) | 0.0659 (8) | −0.0244 (9) | −0.0141 (7) | −0.0139 (9) |
C4A | 0.0884 (10) | 0.0966 (11) | 0.0728 (9) | −0.0324 (9) | −0.0115 (8) | −0.0211 (8) |
C5A | 0.0824 (9) | 0.0698 (8) | 0.0616 (7) | −0.0198 (7) | −0.0100 (7) | −0.0085 (6) |
C6A | 0.0606 (7) | 0.0622 (7) | 0.0483 (6) | −0.0136 (6) | −0.0018 (5) | −0.0035 (5) |
C7A | 0.0630 (7) | 0.0553 (6) | 0.0504 (6) | −0.0131 (5) | −0.0015 (5) | −0.0008 (5) |
C8A | 0.0904 (11) | 0.0643 (8) | 0.0798 (9) | −0.0262 (8) | −0.0274 (9) | 0.0146 (7) |
C9A | 0.0675 (8) | 0.0565 (7) | 0.0590 (6) | −0.0224 (6) | −0.0086 (6) | 0.0056 (5) |
C10A | 0.0710 (8) | 0.0694 (8) | 0.0611 (7) | −0.0180 (7) | −0.0039 (6) | −0.0124 (6) |
C11A | 0.0612 (8) | 0.0661 (8) | 0.0623 (7) | −0.0135 (6) | −0.0020 (6) | −0.0079 (6) |
C12A | 0.0657 (7) | 0.0548 (6) | 0.0540 (6) | −0.0219 (6) | −0.0023 (5) | 0.0014 (5) |
C13A | 0.0722 (8) | 0.0567 (7) | 0.0608 (7) | −0.0193 (6) | −0.0031 (6) | −0.0069 (5) |
C14A | 0.0633 (8) | 0.0569 (7) | 0.0707 (8) | −0.0141 (6) | −0.0028 (6) | −0.0031 (6) |
C15A | 0.0683 (8) | 0.0698 (8) | 0.0683 (8) | −0.0222 (7) | −0.0062 (7) | 0.0007 (6) |
C16A | 0.0873 (12) | 0.0920 (12) | 0.0859 (11) | −0.0392 (10) | −0.0219 (9) | 0.0061 (9) |
N1A | 0.0705 (6) | 0.0592 (6) | 0.0623 (6) | −0.0198 (5) | −0.0123 (5) | 0.0065 (5) |
O1A | 0.0850 (7) | 0.0699 (6) | 0.0903 (7) | −0.0201 (5) | −0.0238 (6) | 0.0230 (5) |
O2A | 0.0698 (5) | 0.0692 (5) | 0.0623 (5) | −0.0225 (4) | −0.0068 (4) | −0.0070 (4) |
Geometric parameters (Å, º) top
C1B—O1B | 1.3443 (15) | C1A—O1A | 1.3486 (16) |
C1B—C2B | 1.3931 (18) | C1A—C2A | 1.387 (2) |
C1B—C6B | 1.4126 (16) | C1A—C6A | 1.4111 (17) |
C2B—C3B | 1.364 (2) | C2A—C3A | 1.369 (2) |
C2B—H2B | 0.954 (17) | C2A—H2A | 0.979 (17) |
C3B—C4B | 1.378 (2) | C3A—C4A | 1.378 (2) |
C3B—H3B | 0.986 (16) | C3A—H3A | 0.924 (16) |
C4B—C5B | 1.3726 (19) | C4A—C5A | 1.366 (2) |
C4B—H4B | 1.012 (16) | C4A—H4A | 0.980 (17) |
C5B—C6B | 1.3994 (17) | C5A—C6A | 1.4051 (18) |
C5B—H5B | 0.965 (15) | C5A—H5A | 0.976 (16) |
C6B—C7B | 1.4689 (16) | C6A—C7A | 1.4681 (17) |
C7B—N1B | 1.2891 (14) | C7A—N1A | 1.2889 (15) |
C7B—C8B | 1.4984 (17) | C7A—C8A | 1.4985 (18) |
C8B—H8D | 0.963 (17) | C8A—H8A | 0.952 (17) |
C8B—H8E | 0.979 (18) | C8A—H8B | 0.954 (17) |
C8B—H8F | 0.97 (2) | C8A—H8C | 0.99 (2) |
C9B—C10B | 1.3807 (17) | C9A—C10A | 1.3811 (17) |
C9B—C14B | 1.3909 (16) | C9A—C14A | 1.3930 (17) |
C9B—N1B | 1.4200 (15) | C9A—N1A | 1.4157 (16) |
C10B—C11B | 1.3797 (18) | C10A—C11A | 1.3803 (19) |
C10B—H10B | 0.967 (14) | C10A—H10A | 0.967 (13) |
C11B—C12B | 1.3861 (15) | C11A—C12A | 1.3864 (16) |
C11B—H11B | 0.934 (15) | C11A—H11A | 0.946 (14) |
C12B—O2B | 1.3706 (14) | C12A—O2A | 1.3665 (15) |
C12B—C13B | 1.3847 (17) | C12A—C13A | 1.3872 (17) |
C13B—C14B | 1.3709 (18) | C13A—C14A | 1.3673 (19) |
C13B—H13B | 0.961 (12) | C13A—H13A | 0.969 (13) |
C14B—H14B | 0.967 (14) | C14A—H14A | 0.942 (13) |
C15B—O2B | 1.4228 (15) | C15A—O2A | 1.4240 (16) |
C15B—C16B | 1.489 (2) | C15A—C16A | 1.491 (2) |
C15B—H15C | 0.948 (15) | C15A—H15A | 0.997 (15) |
C15B—H15D | 1.042 (14) | C15A—H15B | 0.987 (14) |
C16B—H16D | 0.972 (18) | C16A—H16A | 0.984 (19) |
C16B—H16E | 0.949 (18) | C16A—H16B | 1.005 (19) |
C16B—H16F | 1.026 (19) | C16A—H16C | 1.001 (17) |
O1B—H1B | 0.957 (16) | O1A—H1A | 1.06 (2) |
| | | |
O1B—C1B—C2B | 118.50 (12) | O1A—C1A—C2A | 118.40 (13) |
O1B—C1B—C6B | 121.52 (11) | O1A—C1A—C6A | 121.75 (12) |
C2B—C1B—C6B | 119.98 (12) | C2A—C1A—C6A | 119.84 (14) |
C3B—C2B—C1B | 120.47 (14) | C3A—C2A—C1A | 120.48 (16) |
C3B—C2B—H2B | 123.5 (9) | C3A—C2A—H2A | 123.8 (9) |
C1B—C2B—H2B | 116.0 (9) | C1A—C2A—H2A | 115.7 (9) |
C2B—C3B—C4B | 120.77 (14) | C2A—C3A—C4A | 120.95 (16) |
C2B—C3B—H3B | 120.5 (9) | C2A—C3A—H3A | 122.1 (10) |
C4B—C3B—H3B | 118.7 (9) | C4A—C3A—H3A | 117.0 (10) |
C5B—C4B—C3B | 119.49 (14) | C5A—C4A—C3A | 119.23 (16) |
C5B—C4B—H4B | 118.9 (9) | C5A—C4A—H4A | 121.4 (10) |
C3B—C4B—H4B | 121.6 (9) | C3A—C4A—H4A | 119.3 (10) |
C4B—C5B—C6B | 121.95 (14) | C4A—C5A—C6A | 122.04 (15) |
C4B—C5B—H5B | 120.0 (8) | C4A—C5A—H5A | 120.3 (9) |
C6B—C5B—H5B | 118.1 (8) | C6A—C5A—H5A | 117.6 (9) |
C5B—C6B—C1B | 117.34 (12) | C5A—C6A—C1A | 117.45 (12) |
C5B—C6B—C7B | 121.29 (11) | C5A—C6A—C7A | 121.31 (12) |
C1B—C6B—C7B | 121.37 (11) | C1A—C6A—C7A | 121.24 (11) |
N1B—C7B—C6B | 118.22 (10) | N1A—C7A—C6A | 118.25 (11) |
N1B—C7B—C8B | 123.03 (11) | N1A—C7A—C8A | 122.89 (13) |
C6B—C7B—C8B | 118.72 (11) | C6A—C7A—C8A | 118.83 (12) |
C7B—C8B—H8D | 110.2 (9) | C7A—C8A—H8A | 110.6 (10) |
C7B—C8B—H8E | 109.8 (10) | C7A—C8A—H8B | 109.5 (10) |
H8D—C8B—H8E | 109.1 (13) | H8A—C8A—H8B | 110.9 (14) |
C7B—C8B—H8F | 107.7 (12) | C7A—C8A—H8C | 108.3 (11) |
H8D—C8B—H8F | 107.3 (14) | H8A—C8A—H8C | 109.0 (14) |
H8E—C8B—H8F | 112.6 (15) | H8B—C8A—H8C | 108.5 (15) |
C10B—C9B—C14B | 118.24 (12) | C10A—C9A—C14A | 118.07 (12) |
C10B—C9B—N1B | 122.12 (10) | C10A—C9A—N1A | 122.47 (11) |
C14B—C9B—N1B | 119.56 (11) | C14A—C9A—N1A | 119.35 (11) |
C11B—C10B—C9B | 121.51 (11) | C11A—C10A—C9A | 121.58 (12) |
C11B—C10B—H10B | 118.7 (9) | C11A—C10A—H10A | 120.1 (8) |
C9B—C10B—H10B | 119.8 (9) | C9A—C10A—H10A | 118.3 (8) |
C10B—C11B—C12B | 119.52 (12) | C10A—C11A—C12A | 119.63 (12) |
C10B—C11B—H11B | 120.2 (8) | C10A—C11A—H11A | 120.4 (8) |
C12B—C11B—H11B | 120.3 (8) | C12A—C11A—H11A | 119.9 (8) |
O2B—C12B—C13B | 116.01 (10) | O2A—C12A—C11A | 124.84 (11) |
O2B—C12B—C11B | 124.57 (11) | O2A—C12A—C13A | 115.98 (10) |
C13B—C12B—C11B | 119.42 (12) | C11A—C12A—C13A | 119.18 (12) |
C14B—C13B—C12B | 120.45 (11) | C14A—C13A—C12A | 120.63 (11) |
C14B—C13B—H13B | 120.5 (7) | C14A—C13A—H13A | 121.6 (8) |
C12B—C13B—H13B | 119.0 (7) | C12A—C13A—H13A | 117.8 (8) |
C13B—C14B—C9B | 120.77 (12) | C13A—C14A—C9A | 120.87 (13) |
C13B—C14B—H14B | 121.4 (8) | C13A—C14A—H14A | 122.5 (8) |
C9B—C14B—H14B | 117.8 (8) | C9A—C14A—H14A | 116.6 (8) |
O2B—C15B—C16B | 107.75 (12) | O2A—C15A—C16A | 107.67 (13) |
O2B—C15B—H15C | 109.5 (9) | O2A—C15A—H15A | 107.9 (8) |
C16B—C15B—H15C | 110.6 (9) | C16A—C15A—H15A | 111.0 (8) |
O2B—C15B—H15D | 108.2 (8) | O2A—C15A—H15B | 107.6 (8) |
C16B—C15B—H15D | 110.5 (7) | C16A—C15A—H15B | 112.7 (7) |
H15C—C15B—H15D | 110.3 (11) | H15A—C15A—H15B | 109.8 (11) |
C15B—C16B—H16D | 112.3 (10) | C15A—C16A—H16A | 110.3 (10) |
C15B—C16B—H16E | 112.4 (10) | C15A—C16A—H16B | 110.6 (10) |
H16D—C16B—H16E | 106.0 (14) | H16A—C16A—H16B | 105.3 (15) |
C15B—C16B—H16F | 109.5 (10) | C15A—C16A—H16C | 107.6 (9) |
H16D—C16B—H16F | 107.8 (14) | H16A—C16A—H16C | 112.4 (14) |
H16E—C16B—H16F | 108.6 (14) | H16B—C16A—H16C | 110.6 (13) |
C7B—N1B—C9B | 121.74 (10) | C7A—N1A—C9A | 122.57 (10) |
C1B—O1B—H1B | 107.6 (9) | C1A—O1A—H1A | 103.4 (11) |
C12B—O2B—C15B | 118.41 (9) | C12A—O2A—C15A | 118.71 (9) |
| | | |
O1B—C1B—C2B—C3B | −179.04 (12) | O1A—C1A—C2A—C3A | −179.64 (12) |
C6B—C1B—C2B—C3B | 0.81 (18) | C6A—C1A—C2A—C3A | 0.90 (19) |
C1B—C2B—C3B—C4B | −0.6 (2) | C1A—C2A—C3A—C4A | −0.6 (2) |
C2B—C3B—C4B—C5B | 0.1 (2) | C2A—C3A—C4A—C5A | 0.3 (2) |
C3B—C4B—C5B—C6B | 0.23 (19) | C3A—C4A—C5A—C6A | −0.2 (2) |
C4B—C5B—C6B—C1B | −0.06 (17) | C4A—C5A—C6A—C1A | 0.44 (18) |
C4B—C5B—C6B—C7B | 179.52 (11) | C4A—C5A—C6A—C7A | −179.46 (12) |
O1B—C1B—C6B—C5B | 179.39 (10) | O1A—C1A—C6A—C5A | 179.78 (11) |
C2B—C1B—C6B—C5B | −0.45 (16) | C2A—C1A—C6A—C5A | −0.79 (17) |
O1B—C1B—C6B—C7B | −0.19 (16) | O1A—C1A—C6A—C7A | −0.32 (17) |
C2B—C1B—C6B—C7B | 179.97 (10) | C2A—C1A—C6A—C7A | 179.11 (11) |
C5B—C6B—C7B—N1B | −175.84 (10) | C5A—C6A—C7A—N1A | −176.52 (11) |
C1B—C6B—C7B—N1B | 3.72 (15) | C1A—C6A—C7A—N1A | 3.58 (16) |
C5B—C6B—C7B—C8B | 6.05 (16) | C5A—C6A—C7A—C8A | 5.36 (17) |
C1B—C6B—C7B—C8B | −174.39 (12) | C1A—C6A—C7A—C8A | −174.54 (12) |
C14B—C9B—C10B—C11B | −1.76 (19) | C14A—C9A—C10A—C11A | −1.22 (19) |
N1B—C9B—C10B—C11B | −178.53 (12) | N1A—C9A—C10A—C11A | −177.26 (12) |
C9B—C10B—C11B—C12B | −0.8 (2) | C9A—C10A—C11A—C12A | −0.8 (2) |
C10B—C11B—C12B—O2B | −178.45 (11) | C10A—C11A—C12A—O2A | −179.20 (11) |
C10B—C11B—C12B—C13B | 2.13 (19) | C10A—C11A—C12A—C13A | 1.67 (18) |
O2B—C12B—C13B—C14B | 179.72 (11) | O2A—C12A—C13A—C14A | −179.69 (11) |
C11B—C12B—C13B—C14B | −0.81 (19) | C11A—C12A—C13A—C14A | −0.49 (18) |
C12B—C13B—C14B—C9B | −1.84 (19) | C12A—C13A—C14A—C9A | −1.60 (19) |
C10B—C9B—C14B—C13B | 3.09 (18) | C10A—C9A—C14A—C13A | 2.42 (18) |
N1B—C9B—C14B—C13B | 179.95 (11) | N1A—C9A—C14A—C13A | 178.60 (11) |
C6B—C7B—N1B—C9B | 177.59 (10) | C6A—C7A—N1A—C9A | 178.67 (10) |
C8B—C7B—N1B—C9B | −4.38 (17) | C8A—C7A—N1A—C9A | −3.30 (18) |
C10B—C9B—N1B—C7B | −70.37 (15) | C10A—C9A—N1A—C7A | −69.29 (16) |
C14B—C9B—N1B—C7B | 112.89 (13) | C14A—C9A—N1A—C7A | 114.72 (13) |
C13B—C12B—O2B—C15B | −178.92 (11) | C11A—C12A—O2A—C15A | −0.87 (17) |
C11B—C12B—O2B—C15B | 1.64 (17) | C13A—C12A—O2A—C15A | 178.29 (11) |
C16B—C15B—O2B—C12B | −178.64 (11) | C16A—C15A—O2A—C12A | −174.56 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1B—H1B···N1B | 0.957 (16) | 1.681 (16) | 2.5420 (14) | 147.7 (13) |
O1A—H1A···N1A | 1.06 (2) | 1.55 (2) | 2.5415 (14) | 152.3 (18) |