The title compound, C
25H
22ClN
3O
2, was prepared by the reaction of 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one and 4-(4-chlorobenzyloxy)benzaldehyde. The substituted benzaldehyde group makes dihedral angles of 58.85 (5), 6.87 (9) and 47.36 (7)° with the chlorobenzyl ring, the pyrazolone ring and the terminal phenyl ring, respectively. Intermolecular C—H
O hydrogen bonds help to consolidate the crystal packing.
Supporting information
CCDC reference: 610864
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.091
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc.
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
1 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
0 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 83
The title compound, C~25~H~22~Cl~N~3~O~2~, was prepared by the reaction of
If you require a ~ then it should be escaped
with a \, i.e. \~
Otherwise there must be a matching closing ~, e.g. C~2~H~4~
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
(
E)-4-[4-(4-Chlorobenzyloxy)benzylideneamino]-1,5-dimethyl-2-phenyl-
1
H-pyrazol-3(2
H)-one
top
Crystal data top
C25H22ClN3O2 | F(000) = 904 |
Mr = 431.91 | Dx = 1.289 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2085 reflections |
a = 17.038 (6) Å | θ = 2.3–24.2° |
b = 6.916 (2) Å | µ = 0.20 mm−1 |
c = 19.160 (6) Å | T = 294 K |
β = 99.597 (6)° | Block, yellow |
V = 2226.0 (13) Å3 | 0.40 × 0.30 × 0.12 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 4572 independent reflections |
Radiation source: fine-focus sealed tube | 2209 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
φ and ω scans | θmax = 26.6°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −18→21 |
Tmin = 0.920, Tmax = 0.977 | k = −7→8 |
12103 measured reflections | l = −23→23 |
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)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.091 | w = 1/[σ2(Fo2) + (0.0266P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.003 |
4572 reflections | Δρmax = 0.21 e Å−3 |
283 parameters | Δρmin = −0.22 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: 0.0116 (7) |
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 >
2σ(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 | |
Cl1 | 1.47258 (3) | 0.70901 (10) | 1.04163 (3) | 0.0765 (3) | |
O1 | 1.16590 (7) | 0.5835 (2) | 0.77754 (7) | 0.0597 (5) | |
O2 | 0.74676 (8) | 0.6841 (2) | 0.47100 (7) | 0.0588 (4) | |
N1 | 0.88934 (9) | 0.3938 (3) | 0.51734 (8) | 0.0466 (5) | |
N2 | 0.74246 (9) | 0.2698 (2) | 0.36860 (8) | 0.0436 (4) | |
N3 | 0.70736 (9) | 0.4398 (2) | 0.39003 (8) | 0.0434 (4) | |
C1 | 1.30131 (13) | 0.8729 (4) | 0.88487 (11) | 0.0645 (7) | |
H1 | 1.2899 | 0.9801 | 0.8556 | 0.077* | |
C2 | 1.37113 (13) | 0.8691 (4) | 0.93457 (12) | 0.0642 (7) | |
H2 | 1.4062 | 0.9732 | 0.9387 | 0.077* | |
C3 | 1.38739 (11) | 0.7104 (3) | 0.97709 (10) | 0.0481 (6) | |
C4 | 1.33677 (12) | 0.5545 (3) | 0.97069 (11) | 0.0558 (6) | |
H4 | 1.3487 | 0.4462 | 0.9993 | 0.067* | |
C5 | 1.26765 (12) | 0.5606 (4) | 0.92110 (11) | 0.0580 (6) | |
H5 | 1.2333 | 0.4553 | 0.9165 | 0.070* | |
C6 | 1.24901 (12) | 0.7195 (4) | 0.87862 (11) | 0.0503 (6) | |
C7 | 1.17092 (12) | 0.7343 (4) | 0.82863 (11) | 0.0676 (7) | |
H7A | 1.1271 | 0.7237 | 0.8549 | 0.081* | |
H7B | 1.1672 | 0.8589 | 0.8050 | 0.081* | |
C8 | 1.09953 (11) | 0.5827 (3) | 0.72537 (10) | 0.0479 (6) | |
C9 | 1.09657 (11) | 0.4347 (3) | 0.67648 (10) | 0.0527 (6) | |
H9 | 1.1378 | 0.3451 | 0.6803 | 0.063* | |
C10 | 1.03259 (11) | 0.4196 (3) | 0.62199 (10) | 0.0505 (6) | |
H10 | 1.0307 | 0.3184 | 0.5898 | 0.061* | |
C11 | 0.97077 (11) | 0.5546 (3) | 0.61462 (10) | 0.0454 (6) | |
C12 | 0.97591 (12) | 0.7023 (3) | 0.66376 (11) | 0.0602 (7) | |
H12 | 0.9356 | 0.7944 | 0.6595 | 0.072* | |
C13 | 1.03926 (12) | 0.7176 (3) | 0.71917 (10) | 0.0596 (7) | |
H13 | 1.0411 | 0.8177 | 0.7518 | 0.072* | |
C14 | 0.90153 (11) | 0.5414 (3) | 0.55795 (10) | 0.0516 (6) | |
H14 | 0.8654 | 0.6433 | 0.5514 | 0.062* | |
C15 | 0.85526 (12) | 0.0533 (3) | 0.41690 (11) | 0.0616 (7) | |
H15A | 0.9030 | 0.0620 | 0.4513 | 0.092* | |
H15B | 0.8689 | 0.0357 | 0.3707 | 0.092* | |
H15C | 0.8241 | −0.0547 | 0.4280 | 0.092* | |
C16 | 0.80826 (11) | 0.2346 (3) | 0.41805 (10) | 0.0412 (5) | |
C17 | 0.82201 (11) | 0.3849 (3) | 0.46479 (10) | 0.0396 (5) | |
C18 | 0.75865 (11) | 0.5231 (3) | 0.44719 (10) | 0.0418 (5) | |
C19 | 0.68859 (12) | 0.1196 (3) | 0.33516 (11) | 0.0617 (7) | |
H19A | 0.7190 | 0.0090 | 0.3252 | 0.092* | |
H19B | 0.6587 | 0.1683 | 0.2918 | 0.092* | |
H19C | 0.6527 | 0.0828 | 0.3665 | 0.092* | |
C20 | 0.65264 (11) | 0.5481 (3) | 0.34052 (10) | 0.0388 (5) | |
C21 | 0.66043 (12) | 0.5580 (3) | 0.27002 (11) | 0.0505 (6) | |
H21 | 0.7013 | 0.4923 | 0.2536 | 0.061* | |
C22 | 0.60618 (13) | 0.6676 (3) | 0.22393 (12) | 0.0600 (7) | |
H22 | 0.6106 | 0.6741 | 0.1763 | 0.072* | |
C23 | 0.54629 (13) | 0.7662 (3) | 0.24811 (13) | 0.0627 (7) | |
H23 | 0.5104 | 0.8395 | 0.2170 | 0.075* | |
C24 | 0.53930 (13) | 0.7566 (3) | 0.31862 (13) | 0.0603 (7) | |
H24 | 0.4991 | 0.8249 | 0.3352 | 0.072* | |
C25 | 0.59179 (12) | 0.6461 (3) | 0.36472 (11) | 0.0496 (6) | |
H25 | 0.5862 | 0.6376 | 0.4121 | 0.059* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0529 (4) | 0.0848 (5) | 0.0807 (4) | 0.0005 (3) | −0.0207 (3) | −0.0170 (4) |
O1 | 0.0403 (8) | 0.0850 (13) | 0.0494 (8) | 0.0067 (8) | −0.0057 (7) | −0.0247 (9) |
O2 | 0.0649 (10) | 0.0455 (10) | 0.0591 (9) | 0.0017 (8) | −0.0096 (8) | −0.0167 (8) |
N1 | 0.0410 (10) | 0.0576 (14) | 0.0381 (10) | −0.0085 (9) | −0.0028 (9) | 0.0045 (9) |
N2 | 0.0450 (10) | 0.0338 (11) | 0.0474 (10) | −0.0015 (9) | −0.0056 (9) | −0.0064 (9) |
N3 | 0.0480 (10) | 0.0330 (11) | 0.0447 (10) | 0.0026 (9) | −0.0054 (8) | −0.0079 (9) |
C1 | 0.0666 (16) | 0.0664 (19) | 0.0560 (14) | −0.0015 (15) | −0.0027 (13) | 0.0067 (14) |
C2 | 0.0579 (16) | 0.0612 (18) | 0.0695 (16) | −0.0214 (13) | −0.0009 (13) | −0.0021 (14) |
C3 | 0.0377 (12) | 0.0571 (17) | 0.0473 (13) | −0.0031 (12) | 0.0005 (10) | −0.0118 (12) |
C4 | 0.0510 (14) | 0.0572 (17) | 0.0562 (14) | −0.0033 (13) | 0.0002 (12) | 0.0012 (12) |
C5 | 0.0483 (14) | 0.0578 (18) | 0.0645 (15) | −0.0118 (12) | −0.0003 (12) | −0.0084 (14) |
C6 | 0.0420 (13) | 0.0601 (17) | 0.0462 (13) | 0.0014 (13) | 0.0004 (11) | −0.0147 (13) |
C7 | 0.0546 (15) | 0.082 (2) | 0.0593 (14) | 0.0040 (13) | −0.0104 (12) | −0.0253 (14) |
C8 | 0.0338 (12) | 0.0721 (18) | 0.0357 (11) | −0.0019 (12) | −0.0004 (10) | −0.0076 (12) |
C9 | 0.0373 (13) | 0.0720 (18) | 0.0471 (13) | 0.0033 (12) | 0.0021 (11) | −0.0100 (13) |
C10 | 0.0488 (14) | 0.0631 (17) | 0.0392 (12) | −0.0054 (13) | 0.0066 (11) | −0.0102 (11) |
C11 | 0.0416 (13) | 0.0524 (16) | 0.0400 (12) | −0.0043 (12) | 0.0008 (11) | 0.0012 (12) |
C12 | 0.0491 (14) | 0.0619 (17) | 0.0632 (14) | 0.0094 (12) | −0.0093 (12) | −0.0131 (14) |
C13 | 0.0460 (14) | 0.0767 (19) | 0.0517 (14) | 0.0078 (13) | −0.0047 (12) | −0.0208 (13) |
C14 | 0.0474 (13) | 0.0588 (17) | 0.0447 (13) | −0.0068 (12) | −0.0039 (11) | 0.0035 (13) |
C15 | 0.0618 (14) | 0.0488 (16) | 0.0717 (15) | 0.0097 (13) | 0.0036 (12) | 0.0004 (13) |
C16 | 0.0396 (12) | 0.0379 (14) | 0.0449 (12) | −0.0010 (11) | 0.0032 (10) | 0.0059 (11) |
C17 | 0.0404 (12) | 0.0409 (14) | 0.0356 (11) | −0.0059 (11) | 0.0005 (10) | 0.0059 (10) |
C18 | 0.0465 (13) | 0.0357 (14) | 0.0406 (12) | −0.0082 (11) | −0.0006 (10) | −0.0033 (11) |
C19 | 0.0654 (15) | 0.0431 (15) | 0.0712 (15) | −0.0102 (12) | −0.0042 (12) | −0.0154 (13) |
C20 | 0.0358 (12) | 0.0343 (13) | 0.0424 (13) | −0.0035 (10) | −0.0051 (10) | −0.0047 (11) |
C21 | 0.0436 (13) | 0.0572 (16) | 0.0476 (13) | −0.0011 (12) | −0.0021 (11) | −0.0031 (12) |
C22 | 0.0612 (15) | 0.0665 (18) | 0.0465 (13) | −0.0062 (14) | −0.0076 (12) | 0.0063 (13) |
C23 | 0.0519 (15) | 0.0504 (17) | 0.0763 (18) | 0.0043 (13) | −0.0169 (14) | 0.0068 (14) |
C24 | 0.0481 (14) | 0.0473 (16) | 0.0816 (17) | 0.0049 (12) | −0.0005 (13) | −0.0088 (14) |
C25 | 0.0464 (13) | 0.0454 (15) | 0.0549 (13) | −0.0016 (12) | 0.0028 (11) | −0.0039 (12) |
Geometric parameters (Å, º) top
Cl1—C3 | 1.7428 (19) | C10—C11 | 1.397 (3) |
O1—C8 | 1.379 (2) | C10—H10 | 0.9300 |
O1—C7 | 1.423 (2) | C11—C12 | 1.382 (3) |
O2—C18 | 1.233 (2) | C11—C14 | 1.467 (2) |
N1—C14 | 1.279 (2) | C12—C13 | 1.386 (3) |
N1—C17 | 1.396 (2) | C12—H12 | 0.9300 |
N2—C16 | 1.364 (2) | C13—H13 | 0.9300 |
N2—N3 | 1.411 (2) | C14—H14 | 0.9300 |
N2—C19 | 1.462 (2) | C15—C16 | 1.490 (3) |
N3—C18 | 1.405 (2) | C15—H15A | 0.9600 |
N3—C20 | 1.426 (2) | C15—H15B | 0.9600 |
C1—C6 | 1.378 (3) | C15—H15C | 0.9600 |
C1—C2 | 1.395 (3) | C16—C17 | 1.367 (3) |
C1—H1 | 0.9300 | C17—C18 | 1.439 (3) |
C2—C3 | 1.367 (3) | C19—H19A | 0.9600 |
C2—H2 | 0.9300 | C19—H19B | 0.9600 |
C3—C4 | 1.374 (3) | C19—H19C | 0.9600 |
C4—C5 | 1.385 (2) | C20—C21 | 1.381 (3) |
C4—H4 | 0.9300 | C20—C25 | 1.382 (3) |
C5—C6 | 1.373 (3) | C21—C22 | 1.392 (3) |
C5—H5 | 0.9300 | C21—H21 | 0.9300 |
C6—C7 | 1.508 (3) | C22—C23 | 1.371 (3) |
C7—H7A | 0.9700 | C22—H22 | 0.9300 |
C7—H7B | 0.9700 | C23—C24 | 1.377 (3) |
C8—C13 | 1.378 (3) | C23—H23 | 0.9300 |
C8—C9 | 1.382 (3) | C24—C25 | 1.379 (3) |
C9—C10 | 1.382 (2) | C24—H24 | 0.9300 |
C9—H9 | 0.9300 | C25—H25 | 0.9300 |
| | | |
C8—O1—C7 | 116.73 (16) | C13—C12—H12 | 119.0 |
C14—N1—C17 | 120.30 (18) | C8—C13—C12 | 119.2 (2) |
C16—N2—N3 | 106.62 (15) | C8—C13—H13 | 120.4 |
C16—N2—C19 | 124.11 (17) | C12—C13—H13 | 120.4 |
N3—N2—C19 | 117.03 (15) | N1—C14—C11 | 121.9 (2) |
C18—N3—N2 | 109.23 (15) | N1—C14—H14 | 119.0 |
C18—N3—C20 | 123.76 (16) | C11—C14—H14 | 119.0 |
N2—N3—C20 | 120.37 (15) | C16—C15—H15A | 109.5 |
C6—C1—C2 | 120.7 (2) | C16—C15—H15B | 109.5 |
C6—C1—H1 | 119.6 | H15A—C15—H15B | 109.5 |
C2—C1—H1 | 119.6 | C16—C15—H15C | 109.5 |
C3—C2—C1 | 119.1 (2) | H15A—C15—H15C | 109.5 |
C3—C2—H2 | 120.4 | H15B—C15—H15C | 109.5 |
C1—C2—H2 | 120.4 | N2—C16—C17 | 110.52 (18) |
C2—C3—C4 | 121.01 (19) | N2—C16—C15 | 121.45 (18) |
C2—C3—Cl1 | 119.29 (18) | C17—C16—C15 | 128.02 (18) |
C4—C3—Cl1 | 119.68 (18) | C16—C17—N1 | 122.47 (19) |
C3—C4—C5 | 119.1 (2) | C16—C17—C18 | 108.15 (16) |
C3—C4—H4 | 120.4 | N1—C17—C18 | 129.34 (19) |
C5—C4—H4 | 120.4 | O2—C18—N3 | 122.62 (18) |
C6—C5—C4 | 121.2 (2) | O2—C18—C17 | 132.54 (18) |
C6—C5—H5 | 119.4 | N3—C18—C17 | 104.80 (17) |
C4—C5—H5 | 119.4 | N2—C19—H19A | 109.5 |
C5—C6—C1 | 118.8 (2) | N2—C19—H19B | 109.5 |
C5—C6—C7 | 121.6 (2) | H19A—C19—H19B | 109.5 |
C1—C6—C7 | 119.5 (2) | N2—C19—H19C | 109.5 |
O1—C7—C6 | 109.42 (18) | H19A—C19—H19C | 109.5 |
O1—C7—H7A | 109.8 | H19B—C19—H19C | 109.5 |
C6—C7—H7A | 109.8 | C21—C20—C25 | 120.25 (19) |
O1—C7—H7B | 109.8 | C21—C20—N3 | 121.18 (19) |
C6—C7—H7B | 109.8 | C25—C20—N3 | 118.56 (18) |
H7A—C7—H7B | 108.2 | C20—C21—C22 | 119.1 (2) |
C13—C8—O1 | 124.67 (19) | C20—C21—H21 | 120.5 |
C13—C8—C9 | 120.02 (18) | C22—C21—H21 | 120.5 |
O1—C8—C9 | 115.30 (19) | C23—C22—C21 | 120.7 (2) |
C10—C9—C8 | 120.2 (2) | C23—C22—H22 | 119.7 |
C10—C9—H9 | 119.9 | C21—C22—H22 | 119.7 |
C8—C9—H9 | 119.9 | C22—C23—C24 | 119.9 (2) |
C9—C10—C11 | 120.8 (2) | C22—C23—H23 | 120.1 |
C9—C10—H10 | 119.6 | C24—C23—H23 | 120.1 |
C11—C10—H10 | 119.6 | C23—C24—C25 | 120.1 (2) |
C12—C11—C10 | 117.64 (18) | C23—C24—H24 | 119.9 |
C12—C11—C14 | 120.1 (2) | C25—C24—H24 | 119.9 |
C10—C11—C14 | 122.2 (2) | C24—C25—C20 | 120.0 (2) |
C11—C12—C13 | 122.1 (2) | C24—C25—H25 | 120.0 |
C11—C12—H12 | 119.0 | C20—C25—H25 | 120.0 |
| | | |
C16—N2—N3—C18 | 8.5 (2) | C10—C11—C14—N1 | 8.4 (3) |
C19—N2—N3—C18 | 152.56 (16) | N3—N2—C16—C17 | −7.2 (2) |
C16—N2—N3—C20 | 160.99 (16) | C19—N2—C16—C17 | −148.05 (18) |
C19—N2—N3—C20 | −55.0 (2) | N3—N2—C16—C15 | 172.99 (18) |
C6—C1—C2—C3 | 0.2 (3) | C19—N2—C16—C15 | 32.2 (3) |
C1—C2—C3—C4 | 1.1 (3) | N2—C16—C17—N1 | −174.56 (17) |
C1—C2—C3—Cl1 | −177.49 (17) | C15—C16—C17—N1 | 5.2 (3) |
C2—C3—C4—C5 | −1.1 (3) | N2—C16—C17—C18 | 3.3 (2) |
Cl1—C3—C4—C5 | 177.43 (16) | C15—C16—C17—C18 | −177.0 (2) |
C3—C4—C5—C6 | −0.1 (3) | C14—N1—C17—C16 | 176.91 (19) |
C4—C5—C6—C1 | 1.4 (3) | C14—N1—C17—C18 | −0.4 (3) |
C4—C5—C6—C7 | −175.0 (2) | N2—N3—C18—O2 | 171.55 (19) |
C2—C1—C6—C5 | −1.5 (3) | C20—N3—C18—O2 | 20.2 (3) |
C2—C1—C6—C7 | 175.04 (19) | N2—N3—C18—C17 | −6.4 (2) |
C8—O1—C7—C6 | −176.71 (18) | C20—N3—C18—C17 | −157.78 (17) |
C5—C6—C7—O1 | −62.5 (3) | C16—C17—C18—O2 | −175.7 (2) |
C1—C6—C7—O1 | 121.1 (2) | N1—C17—C18—O2 | 2.0 (4) |
C7—O1—C8—C13 | 0.8 (3) | C16—C17—C18—N3 | 2.0 (2) |
C7—O1—C8—C9 | 179.82 (19) | N1—C17—C18—N3 | 179.69 (18) |
C13—C8—C9—C10 | −1.1 (3) | C18—N3—C20—C21 | 115.4 (2) |
O1—C8—C9—C10 | 179.82 (18) | N2—N3—C20—C21 | −32.9 (3) |
C8—C9—C10—C11 | 1.1 (3) | C18—N3—C20—C25 | −63.6 (3) |
C9—C10—C11—C12 | −0.2 (3) | N2—N3—C20—C25 | 148.04 (18) |
C9—C10—C11—C14 | −179.21 (19) | C25—C20—C21—C22 | −0.1 (3) |
C10—C11—C12—C13 | −0.6 (3) | N3—C20—C21—C22 | −179.12 (18) |
C14—C11—C12—C13 | 178.4 (2) | C20—C21—C22—C23 | 0.7 (3) |
O1—C8—C13—C12 | 179.24 (19) | C21—C22—C23—C24 | −0.2 (3) |
C9—C8—C13—C12 | 0.3 (3) | C22—C23—C24—C25 | −0.8 (3) |
C11—C12—C13—C8 | 0.6 (4) | C23—C24—C25—C20 | 1.4 (3) |
C17—N1—C14—C11 | 178.84 (17) | C21—C20—C25—C24 | −1.0 (3) |
C12—C11—C14—N1 | −170.5 (2) | N3—C20—C25—C24 | 178.11 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21···O1i | 0.93 | 2.49 | 3.383 (3) | 161 |
C4—H4···O2ii | 0.93 | 2.56 | 3.220 (3) | 128 |
C15—H15C···O2iii | 0.96 | 2.46 | 3.413 (3) | 173 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, y−1/2, −z+3/2; (iii) x, y−1, z. |