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The title compound, C23H26FNO3·H2O, has been synthesized by the reaction of hydroxylamine with 4-fluorobenzaldehyde and dimedone in ethylene glycol under microwave irradiation. X-ray analysis reveals that the dihydropyridine ring adopts a boat conformation.
Supporting information
CCDC reference: 226869
Key indicators
- Single-crystal X-ray study
- T = 288 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.102
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.14 Ratio
PLAT230_ALERT_2_B Hirshfeld Test Diff for O3 - N .. 9.90 su
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for C16 - C17 .. 5.53 su
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.858(10) ...... 3.00 su-Rat
O3 -H3O 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.858(10) ...... 3.00 su-Rat
O3 -H3O 1.555 1.555
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
3,3,6,6-Tetramethyl-
N-hydroxy-9-(4-fluorophenyl)-1,2,3,4,5,6,7,8,9,10-
decahydroacridine-1,8-dione monohydrate
top
Crystal data top
C23H26FNO3·H2O | Dx = 1.246 Mg m−3 |
Mr = 401.46 | Melting point = 506–507 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.638 (2) Å | Cell parameters from 27 reflections |
b = 14.039 (3) Å | θ = 3.5–14.9° |
c = 12.102 (2) Å | µ = 0.09 mm−1 |
β = 94.60 (1)° | T = 288 K |
V = 2140.2 (6) Å3 | Block, yellow |
Z = 4 | 0.58 × 0.58 × 0.40 mm |
F(000) = 856 | |
Data collection top
Siemens P4 diffractometer | Rint = 0.010 |
Radiation source: normal-focus sealed tube | θmax = 25.0°, θmin = 1.6° |
Graphite monochromator | h = −15→14 |
ω scans | k = −16→0 |
4291 measured reflections | l = 0→14 |
3775 independent reflections | 3 standard reflections every 97 reflections |
2220 reflections with I > 2σ(I) | intensity decay: 2.9% |
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)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.0529P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.91 | (Δ/σ)max < 0.001 |
3775 reflections | Δρmax = 0.14 e Å−3 |
279 parameters | Δρmin = −0.19 e Å−3 |
3 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0083 (9) |
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 | |
F | 0.62144 (12) | 0.55050 (10) | 1.02240 (10) | 0.1055 (5) | |
O1 | 0.75819 (11) | 0.24591 (9) | 0.66659 (12) | 0.0708 (4) | |
O2 | 1.00296 (11) | 0.52808 (10) | 0.70469 (12) | 0.0742 (4) | |
O3 | 0.67704 (12) | 0.54657 (10) | 0.32975 (12) | 0.0680 (4) | |
O4 | 0.79767 (13) | 0.44654 (12) | 0.20835 (13) | 0.0674 (4) | |
N | 0.72058 (12) | 0.51179 (10) | 0.43221 (12) | 0.0487 (4) | |
C1 | 0.65597 (17) | 0.50053 (15) | 0.73571 (17) | 0.0682 (6) | |
H1 | 0.6172 | 0.5033 | 0.6671 | 0.082* | |
C2 | 0.60860 (19) | 0.52916 (16) | 0.82975 (19) | 0.0800 (7) | |
H2 | 0.5390 | 0.5511 | 0.8253 | 0.096* | |
C3 | 0.6679 (2) | 0.52405 (15) | 0.92959 (18) | 0.0694 (6) | |
C4 | 0.76967 (19) | 0.49276 (15) | 0.93904 (17) | 0.0688 (6) | |
H4 | 0.8082 | 0.4906 | 1.0077 | 0.083* | |
C5 | 0.81478 (16) | 0.46420 (14) | 0.84408 (16) | 0.0597 (5) | |
H5 | 0.8843 | 0.4419 | 0.8496 | 0.072* | |
C6 | 0.75919 (15) | 0.46802 (12) | 0.74159 (15) | 0.0490 (5) | |
C7 | 0.81076 (14) | 0.43782 (12) | 0.63735 (14) | 0.0487 (5) | |
H7 | 0.8711 | 0.3965 | 0.6603 | 0.058* | |
C8 | 0.73702 (13) | 0.38243 (12) | 0.55740 (14) | 0.0457 (4) | |
C9 | 0.71578 (15) | 0.28348 (13) | 0.58198 (16) | 0.0529 (5) | |
C10 | 0.64569 (16) | 0.22704 (13) | 0.49936 (16) | 0.0635 (6) | |
H10A | 0.6125 | 0.1761 | 0.5382 | 0.076* | |
H10B | 0.6897 | 0.1980 | 0.4465 | 0.076* | |
C11 | 0.55944 (15) | 0.28546 (14) | 0.43621 (15) | 0.0546 (5) | |
C12 | 0.61260 (14) | 0.37064 (14) | 0.38467 (14) | 0.0542 (5) | |
H12A | 0.6477 | 0.3488 | 0.3209 | 0.065* | |
H12B | 0.5582 | 0.4158 | 0.3584 | 0.065* | |
C13 | 0.69180 (13) | 0.42062 (12) | 0.46214 (14) | 0.0453 (5) | |
C14 | 0.85344 (14) | 0.52388 (12) | 0.57929 (15) | 0.0483 (5) | |
C15 | 0.95122 (16) | 0.56599 (14) | 0.62531 (17) | 0.0564 (5) | |
C16 | 0.99241 (16) | 0.65441 (14) | 0.57301 (17) | 0.0665 (6) | |
H16A | 1.0447 | 0.6359 | 0.5226 | 0.080* | |
H16B | 1.0281 | 0.6934 | 0.6307 | 0.080* | |
C17 | 0.90719 (16) | 0.71428 (13) | 0.50959 (16) | 0.0602 (5) | |
C18 | 0.84094 (16) | 0.64879 (12) | 0.43039 (15) | 0.0597 (5) | |
H18A | 0.7789 | 0.6834 | 0.3997 | 0.072* | |
H18B | 0.8825 | 0.6316 | 0.3694 | 0.072* | |
C19 | 0.80536 (14) | 0.55959 (12) | 0.48446 (15) | 0.0475 (5) | |
C20 | 0.47774 (15) | 0.31841 (15) | 0.51424 (16) | 0.0710 (6) | |
H20A | 0.4476 | 0.2640 | 0.5480 | 0.085* | |
H20B | 0.4226 | 0.3535 | 0.4730 | 0.085* | |
H20C | 0.5116 | 0.3585 | 0.5708 | 0.085* | |
C21 | 0.50381 (18) | 0.22627 (16) | 0.34297 (17) | 0.0791 (7) | |
H21A | 0.5550 | 0.2051 | 0.2938 | 0.095* | |
H21B | 0.4509 | 0.2645 | 0.3026 | 0.095* | |
H21C | 0.4706 | 0.1720 | 0.3739 | 0.095* | |
C22 | 0.83755 (18) | 0.76193 (15) | 0.59084 (18) | 0.0801 (7) | |
H22A | 0.7822 | 0.7974 | 0.5504 | 0.096* | |
H22B | 0.8800 | 0.8043 | 0.6383 | 0.096* | |
H22C | 0.8066 | 0.7141 | 0.6350 | 0.096* | |
C23 | 0.9594 (2) | 0.79083 (15) | 0.44145 (19) | 0.0863 (7) | |
H23A | 1.0070 | 0.7611 | 0.3940 | 0.104* | |
H23B | 0.9982 | 0.8344 | 0.4906 | 0.104* | |
H23C | 0.9055 | 0.8249 | 0.3971 | 0.104* | |
H3O | 0.709 (3) | 0.528 (3) | 0.274 (2) | 0.24 (2)* | |
H4OA | 0.786 (2) | 0.3875 (9) | 0.195 (2) | 0.134 (12)* | |
H4OB | 0.8626 (11) | 0.451 (3) | 0.233 (3) | 0.198 (18)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F | 0.1382 (12) | 0.1118 (11) | 0.0723 (8) | 0.0050 (9) | 0.0447 (9) | −0.0250 (8) |
O1 | 0.0804 (10) | 0.0527 (9) | 0.0788 (10) | 0.0064 (8) | 0.0025 (8) | 0.0184 (8) |
O2 | 0.0582 (8) | 0.0831 (11) | 0.0799 (10) | −0.0068 (8) | −0.0030 (8) | 0.0088 (9) |
O3 | 0.0819 (10) | 0.0599 (9) | 0.0614 (9) | 0.0065 (8) | 0.0009 (8) | 0.0106 (8) |
O4 | 0.0707 (10) | 0.0642 (11) | 0.0665 (10) | −0.0028 (9) | 0.0015 (8) | −0.0091 (8) |
N | 0.0626 (10) | 0.0415 (9) | 0.0418 (9) | 0.0029 (8) | 0.0036 (8) | 0.0049 (7) |
C1 | 0.0783 (15) | 0.0738 (14) | 0.0532 (12) | 0.0238 (12) | 0.0098 (11) | −0.0023 (11) |
C2 | 0.0871 (16) | 0.0834 (17) | 0.0715 (15) | 0.0280 (14) | 0.0192 (14) | −0.0065 (13) |
C3 | 0.0995 (18) | 0.0555 (13) | 0.0566 (14) | −0.0052 (13) | 0.0275 (13) | −0.0097 (11) |
C4 | 0.0887 (17) | 0.0674 (14) | 0.0502 (13) | −0.0178 (13) | 0.0044 (12) | −0.0014 (11) |
C5 | 0.0641 (13) | 0.0592 (13) | 0.0563 (13) | −0.0064 (10) | 0.0074 (11) | 0.0039 (10) |
C6 | 0.0589 (12) | 0.0398 (10) | 0.0489 (11) | 0.0014 (9) | 0.0072 (9) | 0.0039 (9) |
C7 | 0.0503 (11) | 0.0430 (10) | 0.0536 (11) | 0.0073 (9) | 0.0082 (9) | 0.0043 (9) |
C8 | 0.0495 (11) | 0.0399 (10) | 0.0491 (11) | 0.0069 (9) | 0.0124 (9) | −0.0003 (9) |
C9 | 0.0551 (12) | 0.0454 (11) | 0.0601 (12) | 0.0108 (9) | 0.0171 (10) | 0.0073 (10) |
C10 | 0.0709 (14) | 0.0450 (12) | 0.0763 (14) | −0.0015 (11) | 0.0169 (12) | −0.0025 (11) |
C11 | 0.0568 (12) | 0.0521 (12) | 0.0559 (12) | −0.0056 (10) | 0.0110 (10) | −0.0036 (10) |
C12 | 0.0577 (12) | 0.0557 (12) | 0.0497 (11) | −0.0014 (10) | 0.0081 (9) | −0.0033 (10) |
C13 | 0.0494 (11) | 0.0389 (10) | 0.0493 (11) | 0.0057 (9) | 0.0142 (9) | −0.0020 (9) |
C14 | 0.0498 (11) | 0.0434 (11) | 0.0530 (11) | 0.0024 (9) | 0.0116 (9) | −0.0028 (9) |
C15 | 0.0524 (12) | 0.0557 (13) | 0.0626 (13) | 0.0047 (10) | 0.0144 (10) | −0.0048 (11) |
C16 | 0.0620 (13) | 0.0586 (13) | 0.0810 (15) | −0.0077 (11) | 0.0194 (11) | −0.0080 (11) |
C17 | 0.0682 (13) | 0.0426 (11) | 0.0722 (13) | −0.0017 (10) | 0.0210 (11) | −0.0027 (10) |
C18 | 0.0747 (13) | 0.0415 (11) | 0.0650 (13) | −0.0002 (10) | 0.0177 (11) | 0.0048 (10) |
C19 | 0.0523 (11) | 0.0407 (10) | 0.0511 (11) | 0.0062 (9) | 0.0137 (9) | −0.0027 (9) |
C20 | 0.0590 (13) | 0.0806 (15) | 0.0753 (14) | 0.0024 (11) | 0.0169 (11) | 0.0011 (12) |
C21 | 0.0868 (16) | 0.0730 (16) | 0.0776 (15) | −0.0219 (13) | 0.0079 (13) | −0.0091 (12) |
C22 | 0.0897 (16) | 0.0595 (14) | 0.0938 (17) | 0.0063 (12) | 0.0244 (14) | −0.0124 (13) |
C23 | 0.0982 (18) | 0.0585 (14) | 0.1051 (18) | −0.0162 (13) | 0.0259 (15) | 0.0050 (13) |
Geometric parameters (Å, º) top
F—C3 | 1.360 (2) | C11—C21 | 1.527 (2) |
O1—C9 | 1.235 (2) | C11—C12 | 1.529 (2) |
O2—C15 | 1.238 (2) | C12—C13 | 1.491 (2) |
O3—N | 1.4033 (19) | C12—H12A | 0.9700 |
O3—H3O | 0.858 (10) | C12—H12B | 0.9700 |
O4—H4OA | 0.854 (10) | C14—C19 | 1.351 (2) |
O4—H4OB | 0.853 (10) | C14—C15 | 1.441 (3) |
N—C19 | 1.375 (2) | C15—C16 | 1.505 (3) |
N—C13 | 1.387 (2) | C16—C17 | 1.524 (3) |
C1—C6 | 1.378 (3) | C16—H16A | 0.9700 |
C1—C2 | 1.387 (3) | C16—H16B | 0.9700 |
C1—H1 | 0.9300 | C17—C22 | 1.526 (3) |
C2—C3 | 1.372 (3) | C17—C18 | 1.528 (3) |
C2—H2 | 0.9300 | C17—C23 | 1.535 (3) |
C3—C4 | 1.355 (3) | C18—C19 | 1.499 (2) |
C4—C5 | 1.383 (3) | C18—H18A | 0.9700 |
C4—H4 | 0.9300 | C18—H18B | 0.9700 |
C5—C6 | 1.377 (3) | C20—H20A | 0.9600 |
C5—H5 | 0.9300 | C20—H20B | 0.9600 |
C6—C7 | 1.526 (2) | C20—H20C | 0.9600 |
C7—C8 | 1.505 (2) | C21—H21A | 0.9600 |
C7—C14 | 1.518 (2) | C21—H21B | 0.9600 |
C7—H7 | 0.9800 | C21—H21C | 0.9600 |
C8—C13 | 1.355 (2) | C22—H22A | 0.9600 |
C8—C9 | 1.450 (2) | C22—H22B | 0.9600 |
C9—C10 | 1.507 (3) | C22—H22C | 0.9600 |
C10—C11 | 1.520 (3) | C23—H23A | 0.9600 |
C10—H10A | 0.9700 | C23—H23B | 0.9600 |
C10—H10B | 0.9700 | C23—H23C | 0.9600 |
C11—C20 | 1.526 (2) | | |
| | | |
N—O3—H3O | 114 (3) | C8—C13—C12 | 124.38 (17) |
H4OA—O4—H4OB | 107 (3) | N—C13—C12 | 116.56 (16) |
C19—N—C13 | 122.79 (15) | C19—C14—C15 | 119.31 (18) |
C19—N—O3 | 118.20 (14) | C19—C14—C7 | 122.41 (17) |
C13—N—O3 | 117.36 (15) | C15—C14—C7 | 118.23 (17) |
C6—C1—C2 | 121.5 (2) | O2—C15—C14 | 120.45 (18) |
C6—C1—H1 | 119.3 | O2—C15—C16 | 120.11 (19) |
C2—C1—H1 | 119.3 | C14—C15—C16 | 119.38 (19) |
C3—C2—C1 | 117.8 (2) | C15—C16—C17 | 114.35 (17) |
C3—C2—H2 | 121.1 | C15—C16—H16A | 108.7 |
C1—C2—H2 | 121.1 | C17—C16—H16A | 108.7 |
C4—C3—F | 119.2 (2) | C15—C16—H16B | 108.7 |
C4—C3—C2 | 122.6 (2) | C17—C16—H16B | 108.7 |
F—C3—C2 | 118.1 (2) | H16A—C16—H16B | 107.6 |
C3—C4—C5 | 118.4 (2) | C16—C17—C22 | 109.76 (17) |
C3—C4—H4 | 120.8 | C16—C17—C18 | 108.27 (16) |
C5—C4—H4 | 120.8 | C22—C17—C18 | 110.64 (17) |
C6—C5—C4 | 121.5 (2) | C16—C17—C23 | 109.88 (17) |
C6—C5—H5 | 119.2 | C22—C17—C23 | 109.51 (17) |
C4—C5—H5 | 119.2 | C18—C17—C23 | 108.76 (16) |
C5—C6—C1 | 118.16 (18) | C19—C18—C17 | 113.41 (16) |
C5—C6—C7 | 120.87 (17) | C19—C18—H18A | 108.9 |
C1—C6—C7 | 120.96 (17) | C17—C18—H18A | 108.9 |
C8—C7—C14 | 109.78 (14) | C19—C18—H18B | 108.9 |
C8—C7—C6 | 113.06 (14) | C17—C18—H18B | 108.9 |
C14—C7—C6 | 110.65 (14) | H18A—C18—H18B | 107.7 |
C8—C7—H7 | 107.7 | C14—C19—N | 119.38 (16) |
C14—C7—H7 | 107.7 | C14—C19—C18 | 123.41 (18) |
C6—C7—H7 | 107.7 | N—C19—C18 | 117.20 (16) |
C13—C8—C9 | 118.75 (18) | C11—C20—H20A | 109.5 |
C13—C8—C7 | 122.65 (16) | C11—C20—H20B | 109.5 |
C9—C8—C7 | 118.58 (16) | H20A—C20—H20B | 109.5 |
O1—C9—C8 | 120.25 (19) | C11—C20—H20C | 109.5 |
O1—C9—C10 | 121.23 (17) | H20A—C20—H20C | 109.5 |
C8—C9—C10 | 118.44 (17) | H20B—C20—H20C | 109.5 |
C9—C10—C11 | 114.18 (16) | C11—C21—H21A | 109.5 |
C9—C10—H10A | 108.7 | C11—C21—H21B | 109.5 |
C11—C10—H10A | 108.7 | H21A—C21—H21B | 109.5 |
C9—C10—H10B | 108.7 | C11—C21—H21C | 109.5 |
C11—C10—H10B | 108.7 | H21A—C21—H21C | 109.5 |
H10A—C10—H10B | 107.6 | H21B—C21—H21C | 109.5 |
C10—C11—C20 | 110.23 (15) | C17—C22—H22A | 109.5 |
C10—C11—C21 | 110.31 (17) | C17—C22—H22B | 109.5 |
C20—C11—C21 | 109.15 (16) | H22A—C22—H22B | 109.5 |
C10—C11—C12 | 107.83 (16) | C17—C22—H22C | 109.5 |
C20—C11—C12 | 110.90 (16) | H22A—C22—H22C | 109.5 |
C21—C11—C12 | 108.40 (15) | H22B—C22—H22C | 109.5 |
C13—C12—C11 | 113.98 (15) | C17—C23—H23A | 109.5 |
C13—C12—H12A | 108.8 | C17—C23—H23B | 109.5 |
C11—C12—H12A | 108.8 | H23A—C23—H23B | 109.5 |
C13—C12—H12B | 108.8 | C17—C23—H23C | 109.5 |
C11—C12—H12B | 108.8 | H23A—C23—H23C | 109.5 |
H12A—C12—H12B | 107.7 | H23B—C23—H23C | 109.5 |
C8—C13—N | 119.06 (17) | | |
| | | |
C6—C1—C2—C3 | −0.1 (3) | C7—C8—C13—C12 | −175.52 (15) |
C1—C2—C3—C4 | 0.2 (4) | C19—N—C13—C8 | 11.1 (2) |
C1—C2—C3—F | −178.93 (19) | O3—N—C13—C8 | 176.16 (14) |
F—C3—C4—C5 | 178.59 (17) | C19—N—C13—C12 | −168.24 (15) |
C2—C3—C4—C5 | −0.6 (3) | O3—N—C13—C12 | −3.2 (2) |
C3—C4—C5—C6 | 0.7 (3) | C11—C12—C13—C8 | 18.1 (2) |
C4—C5—C6—C1 | −0.6 (3) | C11—C12—C13—N | −162.59 (15) |
C4—C5—C6—C7 | 178.95 (17) | C8—C7—C14—C19 | 19.5 (2) |
C2—C1—C6—C5 | 0.2 (3) | C6—C7—C14—C19 | −106.0 (2) |
C2—C1—C6—C7 | −179.29 (19) | C8—C7—C14—C15 | −157.89 (15) |
C5—C6—C7—C8 | 139.80 (17) | C6—C7—C14—C15 | 76.64 (19) |
C1—C6—C7—C8 | −40.7 (2) | C19—C14—C15—O2 | −171.76 (17) |
C5—C6—C7—C14 | −96.6 (2) | C7—C14—C15—O2 | 5.7 (3) |
C1—C6—C7—C14 | 82.9 (2) | C19—C14—C15—C16 | 5.7 (3) |
C14—C7—C8—C13 | −18.9 (2) | C7—C14—C15—C16 | −176.81 (15) |
C6—C7—C8—C13 | 105.20 (18) | O2—C15—C16—C17 | −157.64 (17) |
C14—C7—C8—C9 | 159.45 (15) | C14—C15—C16—C17 | 24.9 (2) |
C6—C7—C8—C9 | −76.47 (19) | C15—C16—C17—C22 | 70.5 (2) |
C13—C8—C9—O1 | 177.96 (16) | C15—C16—C17—C18 | −50.3 (2) |
C7—C8—C9—O1 | −0.4 (2) | C15—C16—C17—C23 | −168.98 (16) |
C13—C8—C9—C10 | 1.0 (2) | C16—C17—C18—C19 | 48.2 (2) |
C7—C8—C9—C10 | −177.40 (15) | C22—C17—C18—C19 | −72.1 (2) |
O1—C9—C10—C11 | 150.76 (17) | C23—C17—C18—C19 | 167.58 (16) |
C8—C9—C10—C11 | −32.3 (2) | C15—C14—C19—N | 171.05 (15) |
C9—C10—C11—C20 | −68.0 (2) | C7—C14—C19—N | −6.3 (3) |
C9—C10—C11—C21 | 171.40 (15) | C15—C14—C19—C18 | −7.6 (3) |
C9—C10—C11—C12 | 53.2 (2) | C7—C14—C19—C18 | 175.05 (15) |
C10—C11—C12—C13 | −45.9 (2) | C13—N—C19—C14 | −10.5 (2) |
C20—C11—C12—C13 | 74.8 (2) | O3—N—C19—C14 | −175.41 (15) |
C21—C11—C12—C13 | −165.36 (16) | C13—N—C19—C18 | 168.23 (15) |
C9—C8—C13—N | −173.14 (14) | O3—N—C19—C18 | 3.3 (2) |
C7—C8—C13—N | 5.2 (2) | C17—C18—C19—C14 | −21.1 (3) |
C9—C8—C13—C12 | 6.2 (2) | C17—C18—C19—N | 160.23 (15) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3O···O4 | 0.86 (1) | 1.82 (2) | 2.610 (2) | 152 (4) |
O4—H4OA···O1i | 0.85 (1) | 1.93 (1) | 2.786 (2) | 179 (3) |
O4—H4OB···O2ii | 0.85 (1) | 1.83 (1) | 2.675 (2) | 174 (4) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+2, −y+1, −z+1. |
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