In the structure of the title compound, 3-hydroxy-6-methyl-2-[4-(3-trifluoromethylphenyl)piperazin-1-ylmethyl]-4H-pyran-4-one, C18H19F3N2O3, the piperazine ring displays an almost perfect chair conformation, with the substituents at the N atoms lying in equatorial positions. The conformation of the molecule is determined by intra- and intermolecular hydrogen bonds.
Supporting information
CCDC reference: 232168
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.050
- wR factor = 0.121
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT242_ALERT_2_A Check Low U(eq) as Compared to Neighbors .... C18
Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 38 Perc.
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C
GOODF01_ALERT_2_C The least squares goodness of fit parameter lies
outside the range 0.80 <> 2.00
Goodness of fit given = 0.699
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 26.00
From the CIF: _diffrn_reflns_theta_full 0.00
From the CIF: _reflns_number_total 3265
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 3447
Completeness (_total/calc) 94.72%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.95
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.80 mm
PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT410_ALERT_2_C Short Intra H...H Contact H9B .. H13 = 1.98 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 30.60 Deg.
F3A -C18 -F3B 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 26.20 Deg.
F1B -C18 -F1A 1.555 1.555 1.555
1 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
7 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1997) and PARST (Nardelli, 1995).
3-Hydroxy-6-methyl-2-[4-(3-trifluoromethylphenyl)piperazin-1-ylmethyl]-
4
H-pyran-4-one
top
Crystal data top
C18H19F3N2O3 | F(000) = 768 |
Mr = 368.36 | Dx = 1.391 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3360 reflections |
a = 15.5021 (15) Å | θ = 1.9–23.2° |
b = 10.5534 (16) Å | µ = 0.12 mm−1 |
c = 11.2637 (11) Å | T = 293 K |
β = 107.294 (8)° | Prism, colourless |
V = 1759.4 (4) Å3 | 0.80 × 0.32 × 0.06 mm |
Z = 4 | |
Data collection top
Stoe IPDS 2 diffractometer | 1246 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.093 |
Graphite monochromator | θmax = 26.0°, θmin = 2.4° |
Detector resolution: 6.67 pixels mm-1 | h = −19→17 |
rotation method scans | k = −12→12 |
12432 measured reflections | l = −13→12 |
3265 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)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.121 | w = 1/[σ2(Fo2) + (0.0603P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.70 | (Δ/σ)max = 0.001 |
3265 reflections | Δρmax = 0.25 e Å−3 |
256 parameters | Δρmin = −0.18 e Å−3 |
80 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0144 (13) |
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 | Occ. (<1) |
F1A | −0.0917 (11) | 0.4631 (9) | 0.470 (2) | 0.197 (7) | 0.52 (2) |
F1B | −0.1113 (11) | 0.4435 (13) | 0.4203 (14) | 0.137 (4) | 0.48 (2) |
F2 | −0.1658 (3) | 0.4168 (3) | 0.5712 (3) | 0.1874 (15) | |
F3A | −0.2090 (8) | 0.3183 (12) | 0.433 (2) | 0.183 (7) | 0.52 (2) |
F3B | −0.1853 (10) | 0.3176 (14) | 0.3902 (11) | 0.140 (4) | 0.48 (2) |
O1 | 0.50485 (14) | 0.22668 (17) | 0.49483 (18) | 0.0579 (6) | |
O2 | 0.37174 (15) | 0.23843 (17) | 0.17540 (18) | 0.0630 (6) | |
H2 | 0.3759 | 0.2872 | 0.1207 | 0.094* | |
O3 | 0.47424 (17) | 0.4549 (2) | 0.1976 (2) | 0.0772 (7) | |
N1 | 0.31830 (16) | 0.12172 (19) | 0.4600 (2) | 0.0488 (6) | |
N2 | 0.14465 (18) | 0.1282 (2) | 0.5018 (2) | 0.0621 (7) | |
C1 | 0.44188 (19) | 0.1999 (2) | 0.3840 (3) | 0.0460 (7) | |
C2 | 0.5605 (2) | 0.3269 (3) | 0.5041 (3) | 0.0630 (9) | |
C3 | 0.6231 (2) | 0.3385 (3) | 0.6312 (3) | 0.0867 (11) | |
H3A | 0.6122 | 0.2708 | 0.6819 | 0.130* | |
H3B | 0.6135 | 0.4184 | 0.6662 | 0.130* | |
H3C | 0.6843 | 0.3340 | 0.6283 | 0.130* | |
C4 | 0.5541 (2) | 0.4031 (3) | 0.4066 (3) | 0.0662 (9) | |
H4 | 0.5941 | 0.4706 | 0.4160 | 0.079* | |
C5 | 0.4885 (2) | 0.3842 (3) | 0.2895 (3) | 0.0570 (8) | |
C6 | 0.4330 (2) | 0.2696 (3) | 0.2832 (3) | 0.0488 (7) | |
C7 | 0.3842 (2) | 0.0891 (2) | 0.3944 (3) | 0.0536 (8) | |
H7A | 0.3522 | 0.0588 | 0.3117 | 0.064* | |
H7B | 0.4225 | 0.0210 | 0.4384 | 0.064* | |
C8 | 0.2451 (2) | 0.1999 (3) | 0.3824 (3) | 0.0590 (8) | |
H8A | 0.2127 | 0.1526 | 0.3088 | 0.071* | |
H8B | 0.2704 | 0.2750 | 0.3557 | 0.071* | |
C9 | 0.1809 (2) | 0.2384 (3) | 0.4526 (3) | 0.0639 (9) | |
H9A | 0.2120 | 0.2934 | 0.5209 | 0.077* | |
H9B | 0.1313 | 0.2859 | 0.3978 | 0.077* | |
C10 | 0.2771 (2) | 0.0057 (3) | 0.4911 (3) | 0.0593 (8) | |
H10A | 0.3241 | −0.0506 | 0.5390 | 0.071* | |
H10B | 0.2443 | −0.0377 | 0.4152 | 0.071* | |
C11 | 0.2140 (2) | 0.0369 (3) | 0.5645 (3) | 0.0641 (9) | |
H11A | 0.1850 | −0.0403 | 0.5796 | 0.077* | |
H11B | 0.2485 | 0.0711 | 0.6444 | 0.077* | |
C12 | 0.0746 (3) | 0.1499 (3) | 0.5523 (3) | 0.0623 (9) | |
C13 | 0.0107 (2) | 0.2449 (3) | 0.5057 (3) | 0.0701 (9) | |
H13 | 0.0170 | 0.2970 | 0.4422 | 0.084* | |
C14 | −0.0613 (3) | 0.2634 (4) | 0.5513 (3) | 0.0756 (10) | |
C15 | −0.0741 (3) | 0.1880 (4) | 0.6455 (4) | 0.0880 (12) | |
H15 | −0.1225 | 0.2011 | 0.6767 | 0.106* | |
C16 | −0.0123 (3) | 0.0931 (4) | 0.6908 (4) | 0.0897 (12) | |
H16 | −0.0198 | 0.0404 | 0.7532 | 0.108* | |
C17 | 0.0607 (3) | 0.0738 (3) | 0.6461 (3) | 0.0737 (10) | |
H17 | 0.1013 | 0.0088 | 0.6793 | 0.088* | |
C18 | −0.1302 (3) | 0.3597 (4) | 0.4947 (5) | 0.0975 (13) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1A | 0.110 (7) | 0.071 (5) | 0.43 (2) | 0.001 (4) | 0.105 (11) | −0.016 (7) |
F1B | 0.109 (8) | 0.173 (9) | 0.169 (9) | 0.058 (5) | 0.101 (6) | 0.069 (6) |
F2 | 0.211 (4) | 0.193 (3) | 0.203 (3) | 0.072 (3) | 0.130 (3) | −0.022 (3) |
F3A | 0.078 (5) | 0.107 (5) | 0.340 (17) | 0.002 (4) | 0.023 (8) | −0.059 (8) |
F3B | 0.129 (8) | 0.147 (7) | 0.119 (7) | 0.056 (5) | −0.002 (5) | −0.028 (4) |
O1 | 0.0536 (13) | 0.0594 (12) | 0.0627 (13) | 0.0003 (11) | 0.0205 (11) | −0.0011 (10) |
O2 | 0.0716 (16) | 0.0544 (13) | 0.0619 (13) | −0.0133 (11) | 0.0182 (12) | 0.0071 (10) |
O3 | 0.0989 (19) | 0.0640 (14) | 0.0759 (15) | −0.0237 (12) | 0.0371 (14) | 0.0044 (12) |
N1 | 0.0511 (16) | 0.0432 (13) | 0.0578 (15) | −0.0010 (11) | 0.0250 (13) | 0.0054 (11) |
N2 | 0.0633 (18) | 0.0614 (16) | 0.0717 (17) | −0.0085 (14) | 0.0356 (15) | 0.0035 (13) |
C1 | 0.0404 (18) | 0.0485 (17) | 0.0518 (17) | 0.0074 (13) | 0.0180 (15) | −0.0032 (14) |
C2 | 0.055 (2) | 0.071 (2) | 0.067 (2) | −0.0082 (17) | 0.0236 (18) | −0.0120 (18) |
C3 | 0.076 (3) | 0.099 (3) | 0.076 (2) | −0.010 (2) | 0.010 (2) | −0.017 (2) |
C4 | 0.062 (2) | 0.067 (2) | 0.078 (2) | −0.0173 (17) | 0.033 (2) | −0.0168 (18) |
C5 | 0.059 (2) | 0.0532 (18) | 0.069 (2) | −0.0078 (16) | 0.0340 (18) | −0.0108 (17) |
C6 | 0.0464 (19) | 0.0516 (17) | 0.0503 (18) | −0.0019 (14) | 0.0169 (16) | −0.0062 (15) |
C7 | 0.0555 (19) | 0.0476 (17) | 0.062 (2) | 0.0032 (14) | 0.0239 (17) | 0.0052 (14) |
C8 | 0.052 (2) | 0.0628 (19) | 0.068 (2) | 0.0006 (16) | 0.0264 (17) | 0.0103 (15) |
C9 | 0.054 (2) | 0.0621 (19) | 0.083 (2) | 0.0051 (16) | 0.0324 (18) | 0.0175 (17) |
C10 | 0.069 (2) | 0.0453 (17) | 0.072 (2) | −0.0062 (15) | 0.0334 (18) | 0.0010 (15) |
C11 | 0.076 (2) | 0.0503 (18) | 0.074 (2) | −0.0074 (17) | 0.0346 (19) | 0.0053 (16) |
C12 | 0.066 (2) | 0.067 (2) | 0.064 (2) | −0.0195 (18) | 0.0333 (19) | −0.0149 (17) |
C13 | 0.064 (2) | 0.071 (2) | 0.089 (2) | −0.0105 (19) | 0.043 (2) | −0.0158 (19) |
C14 | 0.067 (3) | 0.084 (3) | 0.088 (3) | −0.022 (2) | 0.041 (2) | −0.032 (2) |
C15 | 0.067 (3) | 0.119 (3) | 0.091 (3) | −0.033 (3) | 0.043 (2) | −0.042 (3) |
C16 | 0.082 (3) | 0.118 (3) | 0.083 (3) | −0.035 (3) | 0.045 (3) | −0.011 (2) |
C17 | 0.073 (3) | 0.083 (2) | 0.073 (2) | −0.0212 (19) | 0.034 (2) | −0.0056 (19) |
C18 | 0.082 (3) | 0.101 (3) | 0.131 (4) | −0.006 (3) | 0.064 (3) | −0.033 (3) |
Geometric parameters (Å, º) top
F1A—C18 | 1.311 (9) | C4—H4 | 0.9300 |
F1B—C18 | 1.310 (8) | C5—C6 | 1.474 (4) |
F1B—F3B | 1.72 (2) | C7—H7A | 0.9700 |
F2—C18 | 1.301 (5) | C7—H7B | 0.9700 |
F3A—C18 | 1.289 (9) | C8—C9 | 1.500 (4) |
F3B—C18 | 1.309 (9) | C8—H8A | 0.9700 |
O1—C2 | 1.349 (4) | C8—H8B | 0.9700 |
O1—C1 | 1.366 (3) | C9—H9A | 0.9700 |
O2—C6 | 1.341 (3) | C9—H9B | 0.9700 |
O2—H2 | 0.8200 | C10—C11 | 1.493 (4) |
O3—C5 | 1.241 (3) | C10—H10A | 0.9700 |
N1—C8 | 1.463 (3) | C10—H10B | 0.9700 |
N1—C7 | 1.469 (3) | C11—H11A | 0.9700 |
N1—C10 | 1.470 (3) | C11—H11B | 0.9700 |
N2—C12 | 1.387 (4) | C12—C17 | 1.394 (4) |
N2—C11 | 1.460 (4) | C12—C13 | 1.398 (4) |
N2—C9 | 1.470 (3) | C13—C14 | 1.374 (5) |
C1—C6 | 1.325 (4) | C13—H13 | 0.9300 |
C1—C7 | 1.498 (4) | C14—C15 | 1.387 (5) |
C2—C4 | 1.340 (4) | C14—C18 | 1.475 (6) |
C2—C3 | 1.477 (4) | C15—C16 | 1.375 (5) |
C3—H3A | 0.9600 | C15—H15 | 0.9300 |
C3—H3B | 0.9600 | C16—C17 | 1.384 (5) |
C3—H3C | 0.9600 | C16—H16 | 0.9300 |
C4—C5 | 1.421 (4) | C17—H17 | 0.9300 |
| | | |
C18—F1B—F3B | 48.9 (7) | C8—C9—H9B | 109.2 |
C18—F3B—F1B | 48.9 (7) | H9A—C9—H9B | 107.9 |
C2—O1—C1 | 120.0 (2) | N1—C10—C11 | 110.5 (2) |
C6—O2—H2 | 109.5 | N1—C10—H10A | 109.5 |
C8—N1—C7 | 111.2 (2) | C11—C10—H10A | 109.5 |
C8—N1—C10 | 107.3 (2) | N1—C10—H10B | 109.5 |
C7—N1—C10 | 109.9 (2) | C11—C10—H10B | 109.5 |
C12—N2—C11 | 117.7 (3) | H10A—C10—H10B | 108.1 |
C12—N2—C9 | 117.3 (3) | N2—C11—C10 | 112.8 (3) |
C11—N2—C9 | 113.3 (3) | N2—C11—H11A | 109.0 |
C6—C1—O1 | 122.2 (3) | C10—C11—H11A | 109.0 |
C6—C1—C7 | 126.0 (3) | N2—C11—H11B | 109.0 |
O1—C1—C7 | 111.8 (2) | C10—C11—H11B | 109.0 |
C4—C2—O1 | 121.1 (3) | H11A—C11—H11B | 107.8 |
C4—C2—C3 | 127.7 (3) | N2—C12—C17 | 122.1 (3) |
O1—C2—C3 | 111.2 (3) | N2—C12—C13 | 121.2 (3) |
C2—C3—H3A | 109.5 | C17—C12—C13 | 116.5 (4) |
C2—C3—H3B | 109.5 | C14—C13—C12 | 121.7 (4) |
H3A—C3—H3B | 109.5 | C14—C13—H13 | 119.2 |
C2—C3—H3C | 109.5 | C12—C13—H13 | 119.2 |
H3A—C3—H3C | 109.5 | C13—C14—C15 | 121.4 (4) |
H3B—C3—H3C | 109.5 | C13—C14—C18 | 120.1 (4) |
C2—C4—C5 | 122.3 (3) | C15—C14—C18 | 118.5 (4) |
C2—C4—H4 | 118.8 | C16—C15—C14 | 117.4 (4) |
C5—C4—H4 | 118.8 | C16—C15—H15 | 121.3 |
O3—C5—C4 | 126.2 (3) | C14—C15—H15 | 121.3 |
O3—C5—C6 | 119.8 (3) | C15—C16—C17 | 121.8 (4) |
C4—C5—C6 | 113.9 (3) | C15—C16—H16 | 119.1 |
C1—C6—O2 | 120.4 (3) | C17—C16—H16 | 119.1 |
C1—C6—C5 | 120.3 (3) | C16—C17—C12 | 121.2 (4) |
O2—C6—C5 | 119.4 (3) | C16—C17—H17 | 119.4 |
N1—C7—C1 | 112.1 (2) | C12—C17—H17 | 119.4 |
N1—C7—H7A | 109.2 | F3A—C18—F2 | 89.6 (11) |
C1—C7—H7A | 109.2 | F3A—C18—F3B | 30.6 (12) |
N1—C7—H7B | 109.2 | F2—C18—F3B | 117.4 (8) |
C1—C7—H7B | 109.2 | F3A—C18—F1B | 103.9 (15) |
H7A—C7—H7B | 107.9 | F2—C18—F1B | 109.3 (7) |
N1—C8—C9 | 110.8 (2) | F3B—C18—F1B | 82.2 (13) |
N1—C8—H8A | 109.5 | F3A—C18—F1A | 125.9 (16) |
C9—C8—H8A | 109.5 | F2—C18—F1A | 93.5 (8) |
N1—C8—H8B | 109.5 | F3B—C18—F1A | 108.1 (14) |
C9—C8—H8B | 109.5 | F1B—C18—F1A | 26.2 (11) |
H8A—C8—H8B | 108.1 | F3A—C18—C14 | 116.6 (7) |
N2—C9—C8 | 111.9 (3) | F2—C18—C14 | 115.3 (4) |
N2—C9—H9A | 109.2 | F3B—C18—C14 | 110.5 (7) |
C8—C9—H9A | 109.2 | F1B—C18—C14 | 118.0 (7) |
N2—C9—H9B | 109.2 | F1A—C18—C14 | 110.3 (8) |
| | | |
C2—O1—C1—C6 | 0.1 (4) | C9—N2—C12—C17 | −151.4 (3) |
C2—O1—C1—C7 | −177.4 (3) | C11—N2—C12—C13 | 173.4 (3) |
C1—O1—C2—C4 | 1.3 (5) | C9—N2—C12—C13 | 32.8 (4) |
C1—O1—C2—C3 | −179.9 (3) | N2—C12—C13—C14 | 177.0 (3) |
O1—C2—C4—C5 | 0.8 (5) | C17—C12—C13—C14 | 0.9 (4) |
C3—C2—C4—C5 | −177.7 (3) | C12—C13—C14—C15 | −0.3 (5) |
C2—C4—C5—O3 | 174.8 (3) | C12—C13—C14—C18 | −176.4 (3) |
C2—C4—C5—C6 | −3.9 (4) | C13—C14—C15—C16 | −0.6 (5) |
O1—C1—C6—O2 | 178.4 (2) | C18—C14—C15—C16 | 175.5 (3) |
C7—C1—C6—O2 | −4.5 (5) | C14—C15—C16—C17 | 0.9 (5) |
O1—C1—C6—C5 | −3.4 (4) | C15—C16—C17—C12 | −0.3 (5) |
C7—C1—C6—C5 | 173.6 (3) | N2—C12—C17—C16 | −176.6 (3) |
O3—C5—C6—C1 | −173.7 (3) | C13—C12—C17—C16 | −0.6 (4) |
C4—C5—C6—C1 | 5.1 (4) | F1B—F3B—C18—F3A | 135 (2) |
O3—C5—C6—O2 | 4.5 (4) | F1B—F3B—C18—F2 | 107.8 (9) |
C4—C5—C6—O2 | −176.7 (3) | F1B—F3B—C18—F1A | 3.7 (12) |
C8—N1—C7—C1 | 73.3 (3) | F1B—F3B—C18—C14 | −117.1 (8) |
C10—N1—C7—C1 | −168.0 (2) | F3B—F1B—C18—F3A | −21.8 (11) |
C6—C1—C7—N1 | −103.1 (3) | F3B—F1B—C18—F2 | −116.4 (8) |
O1—C1—C7—N1 | 74.2 (3) | F3B—F1B—C18—F1A | −172 (3) |
C7—N1—C8—C9 | −177.0 (2) | F3B—F1B—C18—C14 | 109.1 (9) |
C10—N1—C8—C9 | 62.7 (3) | C13—C14—C18—F3A | 110.5 (14) |
C12—N2—C9—C8 | −170.6 (3) | C15—C14—C18—F3A | −65.7 (14) |
C11—N2—C9—C8 | 47.1 (3) | C13—C14—C18—F2 | −146.3 (4) |
N1—C8—C9—N2 | −55.7 (3) | C15—C14—C18—F2 | 37.6 (6) |
C8—N1—C10—C11 | −62.3 (3) | C13—C14—C18—F3B | 77.6 (10) |
C7—N1—C10—C11 | 176.6 (2) | C15—C14—C18—F3B | −98.6 (10) |
C12—N2—C11—C10 | 170.6 (2) | C13—C14—C18—F1B | −14.4 (11) |
C9—N2—C11—C10 | −47.3 (3) | C15—C14—C18—F1B | 169.4 (10) |
N1—C10—C11—N2 | 55.4 (3) | C13—C14—C18—F1A | −41.9 (11) |
C11—N2—C12—C17 | −10.8 (4) | C15—C14—C18—F1A | 141.9 (10) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···O2i | 0.97 | 2.59 | 3.270 (4) | 127 |
O2—H2···N1ii | 0.82 | 2.01 | 2.748 (3) | 150 |
O2—H2···O3 | 0.82 | 2.33 | 2.752 (3) | 113 |
C7—H7A···O2 | 0.97 | 2.51 | 2.885 (3) | 103 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2. |