In the title compound, C
24H
18F
3N
3O
2, the dihedral angles formed by the pyrazolone ring with one benzene and two phenyl rings are 26.18 (6), 74.42 (6) and 46.75 (8)°, respectively. The compound is in an enamine–keto form and its structure is stabilized by three intramolecular (N—H
O, C—H
O and C—H
F) and two intermolecular (C—H
O and C—H
F) hydrogen-bond interactions.
Supporting information
CCDC reference: 620523
Key indicators
- Single-crystal X-ray study
- T = 113 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.049
- wR factor = 0.125
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.67 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24
PLAT301_ALERT_3_C Main Residue Disorder ......................... 11.00 Perc.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 18.60 Deg.
C24' -O2 -C24 1.555 1.555 1.555
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: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2004); software used to prepare material for publication: CrystalStructure.
(4
Z)-3-Methyl-1-phenyl-4-{(phenyl)[4-(trifluoromethoxy)anilino]methylene}- 1
H-pyrazol-5(4
H)-one
top
Crystal data top
C24H18F3N3O2 | Z = 2 |
Mr = 437.41 | F(000) = 452 |
Triclinic, P1 | Dx = 1.420 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71070 Å |
a = 8.0696 (9) Å | Cell parameters from 2686 reflections |
b = 11.0945 (12) Å | θ = 1.7–27.9° |
c = 13.1253 (14) Å | µ = 0.11 mm−1 |
α = 106.698 (4)° | T = 113 K |
β = 99.688 (5)° | Platelet, yellow |
γ = 108.459 (9)° | 0.32 × 0.20 × 0.10 mm |
V = 1023.2 (2) Å3 | |
Data collection top
Rigaku Saturn diffractometer | 4770 independent reflections |
Radiation source: Rotating anode | 2854 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.040 |
Detector resolution: 7.31 pixels mm-1 | θmax = 27.9°, θmin = 1.7° |
ω scans | h = −9→10 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −14→12 |
Tmin = 0.966, Tmax = 0.989 | l = −17→16 |
9409 measured 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)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.0558P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.94 | (Δ/σ)max = 0.003 |
4770 reflections | Δρmax = 0.27 e Å−3 |
332 parameters | Δρmin = −0.28 e Å−3 |
175 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: 0.028 (4) |
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) |
O1 | 0.75299 (16) | 0.61087 (13) | 0.75314 (11) | 0.0270 (3) | |
N1 | 1.0507 (2) | 0.76483 (16) | 0.85706 (12) | 0.0234 (4) | |
N2 | 1.1526 (2) | 0.90516 (16) | 0.89128 (13) | 0.0260 (4) | |
N3 | 0.5576 (2) | 0.74522 (17) | 0.68609 (13) | 0.0255 (4) | |
C1 | 0.8722 (2) | 0.72936 (19) | 0.79899 (15) | 0.0230 (4) | |
C2 | 0.8595 (2) | 0.85739 (19) | 0.80125 (15) | 0.0231 (4) | |
C3 | 1.0399 (2) | 0.9593 (2) | 0.85964 (15) | 0.0248 (4) | |
C4 | 1.1115 (3) | 1.10967 (19) | 0.88521 (17) | 0.0315 (5) | |
H4A | 1.2444 | 1.1481 | 0.9159 | 0.047* | |
H4B | 1.0578 | 1.1523 | 0.9395 | 0.047* | |
H4C | 1.0794 | 1.1272 | 0.8170 | 0.047* | |
C5 | 1.1405 (2) | 0.67718 (19) | 0.87229 (15) | 0.0225 (4) | |
C6 | 1.3272 (2) | 0.7184 (2) | 0.88455 (15) | 0.0264 (4) | |
H6 | 1.3951 | 0.8056 | 0.8843 | 0.032* | |
C7 | 1.4128 (3) | 0.6309 (2) | 0.89710 (16) | 0.0304 (5) | |
H7 | 1.5396 | 0.6581 | 0.9045 | 0.036* | |
C8 | 1.3152 (3) | 0.5043 (2) | 0.89891 (16) | 0.0320 (5) | |
H8 | 1.3747 | 0.4448 | 0.9072 | 0.038* | |
C9 | 1.1305 (3) | 0.4651 (2) | 0.88854 (16) | 0.0330 (5) | |
H9 | 1.0634 | 0.3786 | 0.8903 | 0.040* | |
C10 | 1.0423 (3) | 0.5514 (2) | 0.87561 (16) | 0.0280 (4) | |
H10 | 0.9158 | 0.5244 | 0.8691 | 0.034* | |
C11 | 0.7013 (2) | 0.86304 (19) | 0.74477 (15) | 0.0230 (4) | |
C12 | 0.6887 (2) | 0.99317 (19) | 0.74178 (15) | 0.0222 (4) | |
C13 | 0.6850 (2) | 1.0887 (2) | 0.83605 (16) | 0.0262 (4) | |
H13 | 0.6937 | 1.0727 | 0.9037 | 0.031* | |
C14 | 0.6686 (2) | 1.2076 (2) | 0.83042 (16) | 0.0284 (5) | |
H14 | 0.6647 | 1.2727 | 0.8944 | 0.034* | |
C15 | 0.6576 (2) | 1.2319 (2) | 0.73190 (17) | 0.0289 (5) | |
H15 | 0.6480 | 1.3140 | 0.7288 | 0.035* | |
C16 | 0.6608 (2) | 1.1359 (2) | 0.63806 (16) | 0.0285 (5) | |
H16 | 0.6526 | 1.1521 | 0.5705 | 0.034* | |
C17 | 0.6759 (2) | 1.0167 (2) | 0.64273 (16) | 0.0259 (4) | |
H17 | 0.6775 | 0.9509 | 0.5783 | 0.031* | |
C18 | 0.3868 (2) | 0.72462 (19) | 0.61816 (15) | 0.0235 (4) | |
C19 | 0.2873 (2) | 0.8028 (2) | 0.65143 (15) | 0.0251 (4) | |
H19 | 0.3344 | 0.8746 | 0.7220 | 0.030* | |
C20 | 0.1192 (2) | 0.7767 (2) | 0.58221 (16) | 0.0264 (4) | |
H20 | 0.0507 | 0.8299 | 0.6048 | 0.032* | |
C21 | 0.0539 (2) | 0.6720 (2) | 0.48025 (15) | 0.0254 (4) | |
C22 | 0.1491 (2) | 0.5916 (2) | 0.44563 (16) | 0.0259 (4) | |
H22 | 0.1007 | 0.5191 | 0.3755 | 0.031* | |
C23 | 0.3160 (2) | 0.61886 (19) | 0.51503 (15) | 0.0243 (4) | |
H23 | 0.3834 | 0.5648 | 0.4921 | 0.029* | |
O2 | −0.11392 (18) | 0.63400 (15) | 0.40217 (12) | 0.0386 (4) | |
F1 | −0.26439 (18) | 0.7258 (2) | 0.50398 (12) | 0.0570 (6) | 0.921 (3) |
F2 | −0.1170 (2) | 0.83808 (19) | 0.41867 (18) | 0.0663 (7) | 0.921 (3) |
F3 | −0.3549 (3) | 0.6536 (3) | 0.3282 (2) | 0.0758 (9) | 0.921 (3) |
C24 | −0.2077 (3) | 0.7120 (3) | 0.4127 (2) | 0.0391 (7) | 0.921 (3) |
C24' | −0.187 (2) | 0.7195 (14) | 0.3866 (15) | 0.059 (5) | 0.079 (3) |
F1' | −0.195 (3) | 0.807 (2) | 0.4780 (17) | 0.075 (5) | 0.079 (3) |
F2' | −0.081 (3) | 0.7895 (19) | 0.3384 (17) | 0.073 (6) | 0.079 (3) |
F3' | −0.356 (2) | 0.653 (3) | 0.318 (2) | 0.063 (7) | 0.079 (3) |
H3 | 0.581 (3) | 0.671 (3) | 0.6833 (19) | 0.061 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0252 (7) | 0.0205 (8) | 0.0332 (8) | 0.0094 (6) | 0.0046 (6) | 0.0082 (6) |
N1 | 0.0242 (8) | 0.0177 (8) | 0.0280 (9) | 0.0086 (7) | 0.0051 (7) | 0.0086 (7) |
N2 | 0.0279 (8) | 0.0199 (9) | 0.0290 (9) | 0.0086 (7) | 0.0054 (7) | 0.0096 (7) |
N3 | 0.0260 (8) | 0.0212 (9) | 0.0309 (9) | 0.0127 (7) | 0.0053 (7) | 0.0096 (7) |
C1 | 0.0234 (9) | 0.0236 (11) | 0.0226 (10) | 0.0103 (8) | 0.0067 (8) | 0.0079 (8) |
C2 | 0.0277 (9) | 0.0207 (10) | 0.0242 (10) | 0.0126 (8) | 0.0074 (8) | 0.0091 (8) |
C3 | 0.0267 (10) | 0.0238 (11) | 0.0244 (10) | 0.0107 (9) | 0.0060 (8) | 0.0091 (8) |
C4 | 0.0307 (10) | 0.0213 (11) | 0.0387 (12) | 0.0088 (9) | 0.0033 (9) | 0.0106 (9) |
C5 | 0.0274 (10) | 0.0220 (10) | 0.0219 (9) | 0.0139 (9) | 0.0063 (8) | 0.0089 (8) |
C6 | 0.0275 (10) | 0.0294 (11) | 0.0250 (10) | 0.0128 (9) | 0.0067 (8) | 0.0124 (9) |
C7 | 0.0290 (10) | 0.0378 (13) | 0.0278 (11) | 0.0185 (10) | 0.0062 (8) | 0.0115 (9) |
C8 | 0.0371 (11) | 0.0306 (12) | 0.0298 (11) | 0.0218 (10) | 0.0025 (9) | 0.0073 (9) |
C9 | 0.0385 (11) | 0.0237 (11) | 0.0353 (12) | 0.0136 (10) | 0.0030 (9) | 0.0112 (9) |
C10 | 0.0287 (10) | 0.0258 (11) | 0.0301 (11) | 0.0124 (9) | 0.0052 (8) | 0.0107 (9) |
C11 | 0.0271 (9) | 0.0213 (10) | 0.0213 (10) | 0.0106 (8) | 0.0077 (8) | 0.0068 (8) |
C12 | 0.0202 (9) | 0.0199 (10) | 0.0270 (10) | 0.0089 (8) | 0.0050 (7) | 0.0092 (8) |
C13 | 0.0286 (10) | 0.0260 (11) | 0.0262 (10) | 0.0125 (9) | 0.0052 (8) | 0.0118 (8) |
C14 | 0.0295 (10) | 0.0257 (11) | 0.0306 (11) | 0.0142 (9) | 0.0070 (8) | 0.0080 (9) |
C15 | 0.0243 (10) | 0.0228 (11) | 0.0370 (12) | 0.0082 (9) | 0.0013 (8) | 0.0126 (9) |
C16 | 0.0283 (10) | 0.0282 (11) | 0.0301 (11) | 0.0093 (9) | 0.0061 (8) | 0.0152 (9) |
C17 | 0.0279 (10) | 0.0251 (11) | 0.0266 (10) | 0.0107 (9) | 0.0085 (8) | 0.0112 (9) |
C18 | 0.0234 (9) | 0.0228 (10) | 0.0287 (10) | 0.0101 (8) | 0.0086 (8) | 0.0136 (8) |
C19 | 0.0268 (10) | 0.0236 (11) | 0.0254 (10) | 0.0107 (8) | 0.0075 (8) | 0.0082 (8) |
C20 | 0.0255 (10) | 0.0289 (11) | 0.0313 (11) | 0.0165 (9) | 0.0103 (8) | 0.0122 (9) |
C21 | 0.0206 (9) | 0.0279 (11) | 0.0283 (10) | 0.0098 (8) | 0.0048 (8) | 0.0118 (9) |
C22 | 0.0271 (9) | 0.0220 (11) | 0.0293 (11) | 0.0096 (8) | 0.0094 (8) | 0.0095 (8) |
C23 | 0.0256 (9) | 0.0217 (10) | 0.0298 (10) | 0.0120 (8) | 0.0095 (8) | 0.0114 (8) |
O2 | 0.0290 (8) | 0.0412 (10) | 0.0380 (9) | 0.0205 (7) | −0.0019 (6) | 0.0027 (7) |
F1 | 0.0301 (8) | 0.0714 (14) | 0.0512 (10) | 0.0182 (8) | 0.0166 (7) | −0.0049 (9) |
F2 | 0.0783 (12) | 0.0583 (13) | 0.0782 (15) | 0.0378 (11) | 0.0101 (10) | 0.0414 (11) |
F3 | 0.0514 (12) | 0.1042 (18) | 0.0504 (13) | 0.0553 (12) | −0.0156 (10) | −0.0128 (12) |
C24 | 0.0320 (12) | 0.0495 (16) | 0.0340 (14) | 0.0264 (12) | 0.0034 (10) | 0.0043 (12) |
C24' | 0.056 (6) | 0.064 (6) | 0.052 (6) | 0.029 (5) | 0.003 (6) | 0.014 (6) |
F1' | 0.072 (7) | 0.073 (7) | 0.073 (7) | 0.032 (6) | 0.003 (6) | 0.022 (6) |
F2' | 0.076 (8) | 0.075 (9) | 0.060 (8) | 0.021 (7) | 0.012 (7) | 0.029 (7) |
F3' | 0.059 (9) | 0.070 (9) | 0.055 (9) | 0.041 (7) | 0.006 (7) | 0.003 (7) |
Geometric parameters (Å, º) top
O1—C1 | 1.251 (2) | C13—C14 | 1.388 (3) |
N1—C1 | 1.382 (2) | C13—H13 | 0.9500 |
N1—N2 | 1.402 (2) | C14—C15 | 1.389 (3) |
N1—C5 | 1.421 (2) | C14—H14 | 0.9500 |
N2—C3 | 1.313 (2) | C15—C16 | 1.388 (3) |
N3—C11 | 1.344 (2) | C15—H15 | 0.9500 |
N3—C18 | 1.420 (2) | C16—C17 | 1.383 (3) |
N3—H3 | 0.90 (2) | C16—H16 | 0.9500 |
C1—C2 | 1.448 (2) | C17—H17 | 0.9500 |
C2—C11 | 1.394 (2) | C18—C19 | 1.389 (2) |
C2—C3 | 1.438 (3) | C18—C23 | 1.392 (2) |
C3—C4 | 1.494 (3) | C19—C20 | 1.391 (2) |
C4—H4A | 0.9800 | C19—H19 | 0.9500 |
C4—H4B | 0.9800 | C20—C21 | 1.378 (2) |
C4—H4C | 0.9800 | C20—H20 | 0.9500 |
C5—C10 | 1.387 (3) | C21—C22 | 1.382 (2) |
C5—C6 | 1.394 (2) | C21—O2 | 1.409 (2) |
C6—C7 | 1.388 (3) | C22—C23 | 1.381 (2) |
C6—H6 | 0.9500 | C22—H22 | 0.9500 |
C7—C8 | 1.384 (3) | C23—H23 | 0.9500 |
C7—H7 | 0.9500 | O2—C24' | 1.308 (6) |
C8—C9 | 1.384 (3) | O2—C24 | 1.312 (2) |
C8—H8 | 0.9500 | F1—C24 | 1.338 (3) |
C9—C10 | 1.392 (3) | F2—C24 | 1.330 (3) |
C9—H9 | 0.9500 | F3—C24 | 1.311 (3) |
C10—H10 | 0.9500 | C24'—F2' | 1.333 (10) |
C11—C12 | 1.490 (2) | C24'—F1' | 1.334 (10) |
C12—C13 | 1.390 (2) | C24'—F3' | 1.337 (10) |
C12—C17 | 1.392 (3) | | |
| | | |
C1—N1—N2 | 111.85 (14) | C14—C13—H13 | 120.3 |
C1—N1—C5 | 128.24 (16) | C12—C13—H13 | 120.3 |
N2—N1—C5 | 119.42 (14) | C13—C14—C15 | 120.45 (18) |
C3—N2—N1 | 106.66 (15) | C13—C14—H14 | 119.8 |
C11—N3—C18 | 128.61 (17) | C15—C14—H14 | 119.8 |
C11—N3—H3 | 113.5 (15) | C16—C15—C14 | 119.82 (18) |
C18—N3—H3 | 117.3 (15) | C16—C15—H15 | 120.1 |
O1—C1—N1 | 126.04 (17) | C14—C15—H15 | 120.1 |
O1—C1—C2 | 129.19 (16) | C17—C16—C15 | 120.11 (18) |
N1—C1—C2 | 104.74 (15) | C17—C16—H16 | 119.9 |
C11—C2—C3 | 132.47 (18) | C15—C16—H16 | 119.9 |
C11—C2—C1 | 122.00 (17) | C16—C17—C12 | 119.99 (18) |
C3—C2—C1 | 105.20 (15) | C16—C17—H17 | 120.0 |
N2—C3—C2 | 111.48 (17) | C12—C17—H17 | 120.0 |
N2—C3—C4 | 118.65 (17) | C19—C18—C23 | 119.37 (16) |
C2—C3—C4 | 129.85 (16) | C19—C18—N3 | 122.90 (17) |
C3—C4—H4A | 109.5 | C23—C18—N3 | 117.71 (16) |
C3—C4—H4B | 109.5 | C18—C19—C20 | 120.48 (17) |
H4A—C4—H4B | 109.5 | C18—C19—H19 | 119.8 |
C3—C4—H4C | 109.5 | C20—C19—H19 | 119.8 |
H4A—C4—H4C | 109.5 | C21—C20—C19 | 118.65 (16) |
H4B—C4—H4C | 109.5 | C21—C20—H20 | 120.7 |
C10—C5—C6 | 120.29 (17) | C19—C20—H20 | 120.7 |
C10—C5—N1 | 119.86 (16) | C20—C21—C22 | 122.06 (16) |
C6—C5—N1 | 119.85 (17) | C20—C21—O2 | 124.74 (16) |
C7—C6—C5 | 119.35 (19) | C22—C21—O2 | 113.20 (16) |
C7—C6—H6 | 120.3 | C23—C22—C21 | 118.70 (18) |
C5—C6—H6 | 120.3 | C23—C22—H22 | 120.6 |
C8—C7—C6 | 120.71 (18) | C21—C22—H22 | 120.6 |
C8—C7—H7 | 119.6 | C22—C23—C18 | 120.73 (16) |
C6—C7—H7 | 119.6 | C22—C23—H23 | 119.6 |
C9—C8—C7 | 119.56 (18) | C18—C23—H23 | 119.6 |
C9—C8—H8 | 120.2 | C24'—O2—C24 | 18.6 (8) |
C7—C8—H8 | 120.2 | C24'—O2—C21 | 124.4 (8) |
C8—C9—C10 | 120.5 (2) | C24—O2—C21 | 121.31 (17) |
C8—C9—H9 | 119.7 | F3—C24—O2 | 108.4 (2) |
C10—C9—H9 | 119.7 | F3—C24—F2 | 109.2 (2) |
C5—C10—C9 | 119.55 (18) | O2—C24—F2 | 114.4 (2) |
C5—C10—H10 | 120.2 | F3—C24—F1 | 106.4 (2) |
C9—C10—H10 | 120.2 | O2—C24—F1 | 112.3 (2) |
N3—C11—C2 | 118.34 (17) | F2—C24—F1 | 105.9 (2) |
N3—C11—C12 | 118.86 (15) | O2—C24'—F2' | 104.5 (10) |
C2—C11—C12 | 122.71 (16) | O2—C24'—F1' | 115.7 (11) |
C13—C12—C17 | 120.22 (17) | F2'—C24'—F1' | 109.1 (11) |
C13—C12—C11 | 120.49 (16) | O2—C24'—F3' | 110.8 (13) |
C17—C12—C11 | 119.27 (16) | F2'—C24'—F3' | 108.9 (12) |
C14—C13—C12 | 119.40 (17) | F1'—C24'—F3' | 107.6 (12) |
| | | |
C1—N1—N2—C3 | 2.4 (2) | C2—C11—C12—C17 | 110.3 (2) |
C5—N1—N2—C3 | 175.02 (15) | C17—C12—C13—C14 | 0.0 (3) |
N2—N1—C1—O1 | 175.70 (17) | C11—C12—C13—C14 | −178.38 (16) |
C5—N1—C1—O1 | 3.9 (3) | C12—C13—C14—C15 | −0.6 (3) |
N2—N1—C1—C2 | −2.61 (19) | C13—C14—C15—C16 | 0.8 (3) |
C5—N1—C1—C2 | −174.40 (16) | C14—C15—C16—C17 | −0.4 (3) |
O1—C1—C2—C11 | −2.3 (3) | C15—C16—C17—C12 | −0.3 (3) |
N1—C1—C2—C11 | 175.93 (16) | C13—C12—C17—C16 | 0.5 (3) |
O1—C1—C2—C3 | −176.45 (18) | C11—C12—C17—C16 | 178.86 (16) |
N1—C1—C2—C3 | 1.80 (19) | C11—N3—C18—C19 | −46.2 (3) |
N1—N2—C3—C2 | −1.1 (2) | C11—N3—C18—C23 | 135.4 (2) |
N1—N2—C3—C4 | −179.99 (16) | C23—C18—C19—C20 | −0.5 (3) |
C11—C2—C3—N2 | −173.66 (19) | N3—C18—C19—C20 | −178.93 (18) |
C1—C2—C3—N2 | −0.4 (2) | C18—C19—C20—C21 | −0.1 (3) |
C11—C2—C3—C4 | 5.0 (3) | C19—C20—C21—C22 | 0.8 (3) |
C1—C2—C3—C4 | 178.27 (19) | C19—C20—C21—O2 | 179.75 (18) |
C1—N1—C5—C10 | −30.8 (3) | C20—C21—C22—C23 | −1.0 (3) |
N2—N1—C5—C10 | 157.91 (17) | O2—C21—C22—C23 | 179.99 (17) |
C1—N1—C5—C6 | 149.57 (18) | C21—C22—C23—C18 | 0.4 (3) |
N2—N1—C5—C6 | −21.7 (2) | C19—C18—C23—C22 | 0.4 (3) |
C10—C5—C6—C7 | 1.7 (3) | N3—C18—C23—C22 | 178.86 (17) |
N1—C5—C6—C7 | −178.69 (16) | C20—C21—O2—C24' | 34.3 (10) |
C5—C6—C7—C8 | −0.8 (3) | C22—C21—O2—C24' | −146.7 (10) |
C6—C7—C8—C9 | −0.3 (3) | C20—C21—O2—C24 | 12.4 (3) |
C7—C8—C9—C10 | 0.4 (3) | C22—C21—O2—C24 | −168.6 (2) |
C6—C5—C10—C9 | −1.6 (3) | C24'—O2—C24—F3 | 73 (2) |
N1—C5—C10—C9 | 178.85 (16) | C21—O2—C24—F3 | 178.8 (2) |
C8—C9—C10—C5 | 0.5 (3) | C24'—O2—C24—F2 | −49 (2) |
C18—N3—C11—C2 | −176.67 (17) | C21—O2—C24—F2 | 56.7 (3) |
C18—N3—C11—C12 | 0.0 (3) | C24'—O2—C24—F1 | −169 (3) |
C3—C2—C11—N3 | 171.82 (18) | C21—O2—C24—F1 | −63.9 (3) |
C1—C2—C11—N3 | −0.5 (3) | C24—O2—C24'—F2' | 157 (3) |
C3—C2—C11—C12 | −4.7 (3) | C21—O2—C24'—F2' | 70.6 (14) |
C1—C2—C11—C12 | −177.03 (16) | C24—O2—C24'—F1' | 37 (2) |
N3—C11—C12—C13 | 112.2 (2) | C21—O2—C24'—F1' | −49.4 (16) |
C2—C11—C12—C13 | −71.3 (2) | C24—O2—C24'—F3' | −86 (3) |
N3—C11—C12—C17 | −66.2 (2) | C21—O2—C24'—F3' | −172.2 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O1 | 0.90 (2) | 1.92 (2) | 2.6938 (19) | 143 (2) |
C20—H20···F1 | 0.95 | 2.38 | 2.906 (2) | 114 |
C10—H10···O1 | 0.95 | 2.43 | 2.965 (2) | 115 |
C15—H15···F3i | 0.95 | 2.53 | 3.178 (2) | 126 |
C22—H22···O1ii | 0.95 | 2.58 | 3.306 (2) | 133 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1, −y+1, −z+1. |