In the title compound, C
24H
21N
3O
4S, the salicylaldehyde group makes dihedral angles of 2.81 (15), 26.11 (13) and 55.81 (14)°, respectively, with the pyrazolone ring, the phenyl ring attached to S and the phenyl ring attached to N. The crystal packing is stabilized by weak nonclassical intra- and intermolecular C—H
O hydrogen bonds and C—H
π interactions.
Supporting information
CCDC reference: 651463
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.008 Å
- R factor = 0.045
- wR factor = 0.110
- Data-to-parameter ratio = 7.2
checkCIF/PLATON results
No syntax errors found
Alert level C
STRVA01_ALERT_4_C Flack test results are ambiguous.
From the CIF: _refine_ls_abs_structure_Flack 0.500
From the CIF: _refine_ls_abs_structure_Flack_su 0.200
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.16
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C1 -C6 1.36 Ang.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C19 -C24 1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 8
Alert level G
REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may
be needed to determine absolute structure
From the CIF: _diffrn_reflns_theta_max 25.01
From the CIF: _reflns_number_total 2092
Count of symmetry unique reflns 1836
Completeness (_total/calc) 113.94%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 256
Fraction of Friedel pairs measured 0.139
Are heavy atom types Z>Si present yes
PLAT033_ALERT_2_G Flack Parameter Value Deviates 2 * su from zero. 0.50
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
3 ALERT level G = General alerts; check
0 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
3 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
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)-2-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1
H-pyrazol-4-
ylimino)methylene]phenyl benzenesulfonate
top
Crystal data top
C24H21N3O4S | F(000) = 468 |
Mr = 447.51 | Dx = 1.432 Mg m−3 |
Monoclinic, Pc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P -2yc | Cell parameters from 1280 reflections |
a = 8.822 (7) Å | θ = 2.3–23.0° |
b = 10.793 (8) Å | µ = 0.20 mm−1 |
c = 11.029 (8) Å | T = 294 K |
β = 98.896 (13)° | Block, yellow |
V = 1037.5 (14) Å3 | 0.24 × 0.20 × 0.16 mm |
Z = 2 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2092 independent reflections |
Radiation source: fine-focus sealed tube | 1621 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→6 |
Tmin = 0.941, Tmax = 0.969 | k = −12→12 |
4141 measured reflections | l = −10→13 |
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)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.0613P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.007 |
2092 reflections | Δρmax = 0.23 e Å−3 |
292 parameters | Δρmin = −0.43 e Å−3 |
2 restraints | Absolute structure: Flack (1983), with 256 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.5 (2) |
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 | |
S1 | 0.97999 (19) | 0.21638 (11) | 1.21168 (15) | 0.0377 (3) | |
O1 | 0.9790 (5) | 0.2292 (3) | 1.0846 (4) | 0.0569 (11) | |
O2 | 1.1186 (4) | 0.1796 (3) | 1.2858 (4) | 0.0498 (10) | |
O3 | 0.8471 (4) | 0.1231 (3) | 1.2316 (3) | 0.0349 (8) | |
O4 | 0.5268 (5) | 0.2426 (3) | 0.8969 (4) | 0.0457 (10) | |
N1 | 0.6227 (5) | −0.0358 (4) | 0.9182 (4) | 0.0344 (10) | |
N2 | 0.3830 (5) | 0.0603 (4) | 0.6497 (4) | 0.0352 (10) | |
N3 | 0.3897 (5) | 0.1718 (4) | 0.7149 (4) | 0.0356 (10) | |
C1 | 0.9070 (6) | 0.3476 (4) | 1.2737 (5) | 0.0326 (12) | |
C2 | 0.7719 (6) | 0.3989 (5) | 1.2155 (5) | 0.0445 (14) | |
H2 | 0.7192 | 0.3635 | 1.1444 | 0.053* | |
C3 | 0.7171 (7) | 0.5027 (5) | 1.2647 (6) | 0.0503 (15) | |
H3 | 0.6274 | 0.5399 | 1.2262 | 0.060* | |
C4 | 0.7945 (7) | 0.5518 (5) | 1.3709 (6) | 0.0525 (16) | |
H4 | 0.7556 | 0.6212 | 1.4053 | 0.063* | |
C5 | 0.9271 (8) | 0.5003 (5) | 1.4261 (6) | 0.0565 (17) | |
H5 | 0.9796 | 0.5357 | 1.4974 | 0.068* | |
C6 | 0.9846 (7) | 0.3967 (5) | 1.3782 (5) | 0.0472 (15) | |
H6 | 1.0752 | 0.3606 | 1.4167 | 0.057* | |
C7 | 0.8741 (6) | −0.0036 (4) | 1.2073 (5) | 0.0310 (12) | |
C8 | 0.9600 (6) | −0.0697 (5) | 1.2975 (5) | 0.0400 (14) | |
H8 | 1.0012 | −0.0326 | 1.3713 | 0.048* | |
C9 | 0.9845 (7) | −0.1939 (5) | 1.2766 (6) | 0.0488 (16) | |
H9 | 1.0430 | −0.2418 | 1.3364 | 0.059* | |
C10 | 0.9215 (7) | −0.2458 (5) | 1.1664 (5) | 0.0466 (15) | |
H10 | 0.9399 | −0.3289 | 1.1516 | 0.056* | |
C11 | 0.8336 (6) | −0.1786 (5) | 1.0795 (5) | 0.0407 (13) | |
H11 | 0.7915 | −0.2163 | 1.0061 | 0.049* | |
C12 | 0.8048 (6) | −0.0531 (4) | 1.0977 (5) | 0.0330 (12) | |
C13 | 0.7053 (6) | 0.0182 (5) | 1.0053 (5) | 0.0354 (12) | |
H13 | 0.7029 | 0.1041 | 1.0110 | 0.042* | |
C14 | 0.5280 (6) | 0.0286 (4) | 0.8295 (5) | 0.0322 (12) | |
C15 | 0.4563 (6) | −0.0242 (4) | 0.7248 (5) | 0.0319 (12) | |
C16 | 0.4868 (6) | 0.1573 (5) | 0.8240 (5) | 0.0344 (12) | |
C17 | 0.4522 (6) | −0.1582 (4) | 0.6918 (5) | 0.0420 (14) | |
H17A | 0.5216 | −0.2031 | 0.7517 | 0.063* | |
H17B | 0.4822 | −0.1683 | 0.6124 | 0.063* | |
H17C | 0.3500 | −0.1895 | 0.6901 | 0.063* | |
C18 | 0.2493 (7) | 0.0396 (5) | 0.5589 (5) | 0.0477 (14) | |
H18A | 0.2596 | −0.0377 | 0.5180 | 0.072* | |
H18B | 0.2396 | 0.1057 | 0.4999 | 0.072* | |
H18C | 0.1595 | 0.0372 | 0.5982 | 0.072* | |
C19 | 0.3770 (6) | 0.2864 (5) | 0.6480 (5) | 0.0365 (12) | |
C20 | 0.4375 (7) | 0.2975 (5) | 0.5430 (5) | 0.0448 (15) | |
H20 | 0.4845 | 0.2305 | 0.5109 | 0.054* | |
C21 | 0.4276 (8) | 0.4120 (6) | 0.4845 (6) | 0.0566 (16) | |
H21 | 0.4637 | 0.4213 | 0.4102 | 0.068* | |
C22 | 0.3647 (8) | 0.5108 (6) | 0.5361 (7) | 0.0622 (18) | |
H22 | 0.3632 | 0.5881 | 0.4989 | 0.075* | |
C23 | 0.3041 (8) | 0.4971 (5) | 0.6415 (6) | 0.0539 (17) | |
H23 | 0.2591 | 0.5645 | 0.6747 | 0.065* | |
C24 | 0.3093 (7) | 0.3838 (5) | 0.6991 (5) | 0.0459 (15) | |
H24 | 0.2679 | 0.3735 | 0.7711 | 0.055* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0431 (8) | 0.0266 (7) | 0.0442 (8) | −0.0009 (7) | 0.0091 (6) | −0.0030 (7) |
O1 | 0.089 (3) | 0.038 (2) | 0.048 (3) | −0.006 (2) | 0.027 (2) | −0.0044 (19) |
O2 | 0.038 (2) | 0.035 (2) | 0.073 (3) | 0.0053 (19) | −0.0031 (19) | −0.0066 (19) |
O3 | 0.036 (2) | 0.0218 (17) | 0.047 (2) | −0.0015 (15) | 0.0076 (15) | −0.0009 (15) |
O4 | 0.061 (3) | 0.025 (2) | 0.046 (2) | 0.0008 (18) | −0.0059 (19) | −0.0012 (17) |
N1 | 0.038 (2) | 0.028 (2) | 0.038 (3) | 0.002 (2) | 0.009 (2) | −0.001 (2) |
N2 | 0.044 (3) | 0.024 (2) | 0.035 (2) | −0.002 (2) | −0.003 (2) | −0.0018 (19) |
N3 | 0.045 (3) | 0.024 (2) | 0.036 (2) | −0.002 (2) | −0.001 (2) | 0.0014 (18) |
C1 | 0.035 (3) | 0.024 (3) | 0.038 (3) | 0.000 (2) | 0.004 (2) | 0.001 (2) |
C2 | 0.045 (3) | 0.031 (3) | 0.054 (4) | 0.001 (3) | −0.002 (3) | 0.001 (3) |
C3 | 0.049 (4) | 0.039 (3) | 0.063 (4) | 0.010 (3) | 0.009 (3) | 0.008 (3) |
C4 | 0.067 (4) | 0.026 (3) | 0.067 (4) | 0.009 (3) | 0.018 (3) | −0.003 (3) |
C5 | 0.070 (5) | 0.036 (3) | 0.057 (4) | 0.003 (3) | −0.008 (3) | −0.013 (3) |
C6 | 0.046 (3) | 0.034 (3) | 0.058 (4) | 0.008 (3) | −0.004 (3) | 0.000 (3) |
C7 | 0.037 (3) | 0.019 (2) | 0.038 (3) | 0.004 (2) | 0.009 (2) | 0.000 (2) |
C8 | 0.045 (3) | 0.038 (3) | 0.036 (3) | 0.003 (3) | 0.001 (3) | −0.002 (2) |
C9 | 0.053 (4) | 0.034 (3) | 0.057 (4) | 0.008 (3) | −0.001 (3) | 0.011 (3) |
C10 | 0.054 (4) | 0.024 (3) | 0.060 (4) | 0.006 (3) | 0.004 (3) | −0.001 (3) |
C11 | 0.047 (3) | 0.028 (3) | 0.046 (3) | 0.003 (3) | 0.003 (3) | −0.007 (2) |
C12 | 0.035 (3) | 0.024 (3) | 0.042 (3) | 0.001 (2) | 0.008 (2) | 0.001 (2) |
C13 | 0.041 (3) | 0.023 (3) | 0.041 (3) | 0.000 (2) | 0.004 (2) | −0.003 (2) |
C14 | 0.034 (3) | 0.027 (3) | 0.034 (3) | −0.003 (2) | 0.000 (2) | 0.003 (2) |
C15 | 0.035 (3) | 0.023 (2) | 0.038 (3) | −0.007 (2) | 0.009 (2) | −0.001 (2) |
C16 | 0.044 (3) | 0.025 (3) | 0.036 (3) | −0.007 (2) | 0.009 (3) | −0.001 (2) |
C17 | 0.044 (4) | 0.026 (3) | 0.057 (4) | 0.001 (2) | 0.011 (3) | −0.007 (3) |
C18 | 0.052 (3) | 0.037 (3) | 0.050 (3) | −0.002 (3) | −0.004 (3) | −0.004 (3) |
C19 | 0.038 (3) | 0.030 (3) | 0.038 (3) | −0.001 (2) | −0.003 (2) | 0.006 (2) |
C20 | 0.053 (4) | 0.041 (4) | 0.040 (4) | −0.002 (3) | 0.006 (3) | 0.004 (3) |
C21 | 0.062 (4) | 0.059 (4) | 0.049 (4) | −0.011 (4) | 0.009 (3) | 0.011 (3) |
C22 | 0.073 (5) | 0.037 (4) | 0.070 (5) | −0.003 (3) | −0.010 (4) | 0.019 (3) |
C23 | 0.068 (5) | 0.027 (3) | 0.062 (4) | 0.001 (3) | −0.005 (4) | 0.001 (3) |
C24 | 0.045 (3) | 0.035 (3) | 0.055 (4) | −0.001 (3) | −0.002 (3) | 0.005 (3) |
Geometric parameters (Å, º) top
S1—O1 | 1.408 (4) | C9—C10 | 1.375 (7) |
S1—O2 | 1.418 (4) | C9—H9 | 0.930 |
S1—O3 | 1.586 (4) | C10—C11 | 1.348 (7) |
S1—C1 | 1.739 (5) | C10—H10 | 0.930 |
O3—C7 | 1.421 (5) | C11—C12 | 1.398 (7) |
O4—C16 | 1.237 (6) | C11—H11 | 0.930 |
N1—C13 | 1.256 (6) | C12—C13 | 1.457 (7) |
N1—C14 | 1.373 (6) | C13—H13 | 0.930 |
N2—C15 | 1.331 (6) | C14—C15 | 1.353 (7) |
N2—N3 | 1.398 (6) | C14—C16 | 1.436 (7) |
N2—C18 | 1.442 (7) | C15—C17 | 1.490 (7) |
N3—C16 | 1.374 (6) | C17—H17A | 0.960 |
N3—C19 | 1.435 (6) | C17—H17B | 0.960 |
C1—C6 | 1.354 (7) | C17—H17C | 0.960 |
C1—C2 | 1.379 (7) | C18—H18A | 0.960 |
C2—C3 | 1.365 (8) | C18—H18B | 0.960 |
C2—H2 | 0.930 | C18—H18C | 0.960 |
C3—C4 | 1.367 (8) | C19—C20 | 1.354 (8) |
C3—H3 | 0.930 | C19—C24 | 1.373 (8) |
C4—C5 | 1.352 (8) | C20—C21 | 1.390 (8) |
C4—H4 | 0.930 | C20—H20 | 0.930 |
C5—C6 | 1.368 (8) | C21—C22 | 1.366 (10) |
C5—H5 | 0.930 | C21—H21 | 0.930 |
C6—H6 | 0.930 | C22—C23 | 1.360 (10) |
C7—C8 | 1.357 (7) | C22—H22 | 0.930 |
C7—C12 | 1.376 (7) | C23—C24 | 1.376 (8) |
C8—C9 | 1.382 (8) | C23—H23 | 0.930 |
C8—H8 | 0.930 | C24—H24 | 0.930 |
| | | |
O1—S1—O2 | 118.3 (3) | C12—C11—H11 | 119.4 |
O1—S1—O3 | 108.0 (2) | C7—C12—C11 | 115.9 (4) |
O2—S1—O3 | 109.4 (2) | C7—C12—C13 | 123.1 (4) |
O1—S1—C1 | 111.5 (2) | C11—C12—C13 | 121.0 (5) |
O2—S1—C1 | 109.9 (2) | N1—C13—C12 | 120.3 (5) |
O3—S1—C1 | 97.8 (2) | N1—C13—H13 | 119.8 |
C7—O3—S1 | 115.8 (3) | C12—C13—H13 | 119.8 |
C13—N1—C14 | 121.8 (4) | C15—C14—N1 | 123.2 (4) |
C15—N2—N3 | 107.0 (4) | C15—C14—C16 | 106.8 (4) |
C15—N2—C18 | 126.4 (4) | N1—C14—C16 | 130.0 (5) |
N3—N2—C18 | 117.1 (4) | N2—C15—C14 | 111.1 (4) |
C16—N3—N2 | 108.9 (4) | N2—C15—C17 | 121.5 (5) |
C16—N3—C19 | 122.4 (4) | C14—C15—C17 | 127.4 (5) |
N2—N3—C19 | 119.0 (4) | O4—C16—N3 | 124.2 (5) |
C6—C1—C2 | 121.7 (5) | O4—C16—C14 | 130.4 (5) |
C6—C1—S1 | 118.9 (4) | N3—C16—C14 | 105.5 (4) |
C2—C1—S1 | 119.3 (4) | C15—C17—H17A | 109.5 |
C3—C2—C1 | 118.6 (5) | C15—C17—H17B | 109.5 |
C3—C2—H2 | 120.7 | H17A—C17—H17B | 109.5 |
C1—C2—H2 | 120.7 | C15—C17—H17C | 109.5 |
C2—C3—C4 | 119.8 (5) | H17A—C17—H17C | 109.5 |
C2—C3—H3 | 120.1 | H17B—C17—H17C | 109.5 |
C4—C3—H3 | 120.1 | N2—C18—H18A | 109.5 |
C5—C4—C3 | 120.6 (5) | N2—C18—H18B | 109.5 |
C5—C4—H4 | 119.7 | H18A—C18—H18B | 109.5 |
C3—C4—H4 | 119.7 | N2—C18—H18C | 109.5 |
C4—C5—C6 | 120.6 (5) | H18A—C18—H18C | 109.5 |
C4—C5—H5 | 119.7 | H18B—C18—H18C | 109.5 |
C6—C5—H5 | 119.7 | C20—C19—C24 | 122.5 (5) |
C1—C6—C5 | 118.6 (5) | C20—C19—N3 | 120.4 (5) |
C1—C6—H6 | 120.7 | C24—C19—N3 | 117.0 (5) |
C5—C6—H6 | 120.7 | C19—C20—C21 | 118.1 (6) |
C8—C7—C12 | 124.2 (4) | C19—C20—H20 | 121.0 |
C8—C7—O3 | 117.3 (4) | C21—C20—H20 | 121.0 |
C12—C7—O3 | 118.4 (4) | C22—C21—C20 | 120.0 (6) |
C7—C8—C9 | 118.1 (5) | C22—C21—H21 | 120.0 |
C7—C8—H8 | 120.9 | C20—C21—H21 | 120.0 |
C9—C8—H8 | 120.9 | C23—C22—C21 | 120.7 (6) |
C10—C9—C8 | 119.4 (5) | C23—C22—H22 | 119.7 |
C10—C9—H9 | 120.3 | C21—C22—H22 | 119.7 |
C8—C9—H9 | 120.3 | C22—C23—C24 | 120.1 (6) |
C11—C10—C9 | 121.2 (5) | C22—C23—H23 | 120.0 |
C11—C10—H10 | 119.4 | C24—C23—H23 | 120.0 |
C9—C10—H10 | 119.4 | C19—C24—C23 | 118.5 (6) |
C10—C11—C12 | 121.1 (5) | C19—C24—H24 | 120.7 |
C10—C11—H11 | 119.4 | C23—C24—H24 | 120.7 |
| | | |
O1—S1—O3—C7 | 72.8 (4) | C14—N1—C13—C12 | −179.8 (5) |
O2—S1—O3—C7 | −57.2 (4) | C7—C12—C13—N1 | −166.6 (5) |
C1—S1—O3—C7 | −171.5 (3) | C11—C12—C13—N1 | 12.6 (7) |
C15—N2—N3—C16 | 8.6 (6) | C13—N1—C14—C15 | 169.3 (5) |
C18—N2—N3—C16 | 157.1 (5) | C13—N1—C14—C16 | −9.3 (8) |
C15—N2—N3—C19 | 155.4 (4) | N3—N2—C15—C14 | −8.1 (6) |
C18—N2—N3—C19 | −56.1 (6) | C18—N2—C15—C14 | −152.9 (6) |
O1—S1—C1—C6 | −133.2 (5) | N3—N2—C15—C17 | 171.0 (5) |
O2—S1—C1—C6 | −0.1 (5) | C18—N2—C15—C17 | 26.3 (8) |
O3—S1—C1—C6 | 113.9 (4) | N1—C14—C15—N2 | −174.3 (5) |
O1—S1—C1—C2 | 47.0 (5) | C16—C14—C15—N2 | 4.6 (6) |
O2—S1—C1—C2 | −179.9 (4) | N1—C14—C15—C17 | 6.6 (8) |
O3—S1—C1—C2 | −65.9 (5) | C16—C14—C15—C17 | −174.5 (5) |
C6—C1—C2—C3 | 0.8 (8) | N2—N3—C16—O4 | 173.5 (5) |
S1—C1—C2—C3 | −179.3 (5) | C19—N3—C16—O4 | 28.0 (8) |
C1—C2—C3—C4 | −1.4 (9) | N2—N3—C16—C14 | −5.7 (6) |
C2—C3—C4—C5 | 1.6 (9) | C19—N3—C16—C14 | −151.1 (5) |
C3—C4—C5—C6 | −1.3 (10) | C15—C14—C16—O4 | −178.2 (5) |
C2—C1—C6—C5 | −0.5 (9) | N1—C14—C16—O4 | 0.6 (10) |
S1—C1—C6—C5 | 179.6 (5) | C15—C14—C16—N3 | 0.8 (6) |
C4—C5—C6—C1 | 0.7 (10) | N1—C14—C16—N3 | 179.6 (5) |
S1—O3—C7—C8 | 82.5 (5) | C16—N3—C19—C20 | 107.0 (6) |
S1—O3—C7—C12 | −101.4 (5) | N2—N3—C19—C20 | −35.1 (7) |
C12—C7—C8—C9 | 2.6 (8) | C16—N3—C19—C24 | −69.4 (7) |
O3—C7—C8—C9 | 178.5 (5) | N2—N3—C19—C24 | 148.4 (5) |
C7—C8—C9—C10 | −0.2 (9) | C24—C19—C20—C21 | −1.2 (9) |
C8—C9—C10—C11 | −1.4 (9) | N3—C19—C20—C21 | −177.4 (5) |
C9—C10—C11—C12 | 0.7 (9) | C19—C20—C21—C22 | 3.1 (9) |
C8—C7—C12—C11 | −3.2 (8) | C20—C21—C22—C23 | −3.4 (10) |
O3—C7—C12—C11 | −179.1 (4) | C21—C22—C23—C24 | 1.7 (10) |
C8—C7—C12—C13 | 176.1 (5) | C20—C19—C24—C23 | −0.5 (8) |
O3—C7—C12—C13 | 0.2 (7) | N3—C19—C24—C23 | 175.9 (5) |
C10—C11—C12—C7 | 1.5 (8) | C22—C23—C24—C19 | 0.2 (9) |
C10—C11—C12—C13 | −177.8 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···O4 | 0.93 | 2.37 | 3.032 (6) | 128 |
C4—H4···O4i | 0.93 | 2.49 | 3.286 (7) | 144 |
C17—H17C···O2ii | 0.96 | 2.44 | 3.276 (7) | 145 |
C3—H3···Cgi | 0.93 | 2.60 | 3.516 (2) | 168 |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) x−1, −y, z−1/2. |