The acenaphthene keto O atom of the title compound, C
31H
24N
2O
4·0.5H
2O, is displaced by 0.132 (2) Å from the acenaphthene plane, while the indole keto O atom is displaced by only 0.096 (2) Å from the oxindole plane. The molecular structure is stabilized by intramolecular C—H
O interactions. The crystal packing is stabilized by C—H
O, N—H
O and N—H
N intermolecular interactions.
Supporting information
CCDC reference: 242327
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.083
- wR factor = 0.219
- Data-to-parameter ratio = 16.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.26 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.80 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 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
1 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
4'-(4-Methoxybenzoyl)-1'-methyl-acenaphthene-1-spiro-2'-pyrrolidine-
3'-spiro-3''-1
H-indole-2,2''(1
H,3''H)-dione hemihydrate
top
Crystal data top
C31H24N2O4·0.5H2O | F(000) = 2088 |
Mr = 497.53 | Dx = 1.310 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 25.647 (2) Å | Cell parameters from 1300 reflections |
b = 10.0538 (9) Å | θ = 2.2–20.7° |
c = 21.0859 (18) Å | µ = 0.09 mm−1 |
β = 111.933 (2)° | T = 293 K |
V = 5043.5 (7) Å3 | Block, colorless |
Z = 8 | 0.21 × 0.20 × 0.20 mm |
Data collection top
CCD Area Detector diffractometer | 3290 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.045 |
Graphite monochromator | θmax = 28.0°, θmin = 1.7° |
ω scans | h = −32→26 |
15002 measured reflections | k = −13→12 |
5795 independent reflections | l = −26→27 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.084 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.219 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0971P)2 + 2.3543P] where P = (Fo2 + 2Fc2)/3 |
5795 reflections | (Δ/σ)max < 0.001 |
345 parameters | Δρmax = 0.24 e Å−3 |
2 restraints | Δρmin = −0.40 e Å−3 |
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 | |
N1 | 0.20546 (11) | 0.6868 (2) | 0.31750 (12) | 0.0481 (6) | |
C2 | 0.19908 (12) | 0.5530 (3) | 0.34153 (14) | 0.0405 (7) | |
C3 | 0.16911 (11) | 0.4748 (3) | 0.27255 (13) | 0.0380 (7) | |
C4 | 0.13731 (13) | 0.5872 (3) | 0.22016 (16) | 0.0507 (8) | |
H4 | 0.1552 | 0.5918 | 0.1864 | 0.061* | |
C5 | 0.15224 (15) | 0.7162 (3) | 0.26104 (17) | 0.0586 (9) | |
H5A | 0.1568 | 0.7885 | 0.2331 | 0.070* | |
H5B | 0.1233 | 0.7401 | 0.2782 | 0.070* | |
C6 | 0.16272 (14) | 0.5515 (3) | 0.38729 (16) | 0.0487 (8) | |
C7 | 0.19589 (15) | 0.4869 (3) | 0.45229 (15) | 0.0501 (8) | |
C8 | 0.18413 (18) | 0.4570 (4) | 0.50962 (18) | 0.0692 (11) | |
H8 | 0.1490 | 0.4747 | 0.5111 | 0.083* | |
C9 | 0.2271 (2) | 0.3988 (4) | 0.56548 (19) | 0.0818 (14) | |
H9 | 0.2196 | 0.3756 | 0.6039 | 0.098* | |
C10 | 0.2789 (2) | 0.3752 (4) | 0.56536 (18) | 0.0799 (13) | |
H10 | 0.3061 | 0.3377 | 0.6038 | 0.096* | |
C11 | 0.29264 (17) | 0.4062 (3) | 0.50828 (16) | 0.0602 (10) | |
C12 | 0.34453 (18) | 0.3916 (4) | 0.5021 (2) | 0.0769 (12) | |
H12 | 0.3748 | 0.3566 | 0.5382 | 0.092* | |
C13 | 0.35103 (15) | 0.4286 (4) | 0.4433 (2) | 0.0722 (11) | |
H13 | 0.3860 | 0.4181 | 0.4403 | 0.087* | |
C14 | 0.30656 (13) | 0.4824 (3) | 0.38690 (18) | 0.0583 (9) | |
H14 | 0.3125 | 0.5081 | 0.3477 | 0.070* | |
C15 | 0.25491 (13) | 0.4964 (3) | 0.39051 (14) | 0.0439 (7) | |
C16 | 0.24873 (14) | 0.4592 (3) | 0.45187 (15) | 0.0481 (8) | |
C17 | 0.21367 (12) | 0.4140 (3) | 0.24859 (14) | 0.0381 (6) | |
N18 | 0.20791 (10) | 0.2805 (2) | 0.24663 (12) | 0.0408 (6) | |
H18 | 0.2299 | 0.2264 | 0.2370 | 0.049* | |
C19 | 0.16145 (11) | 0.2407 (3) | 0.26223 (13) | 0.0396 (7) | |
C20 | 0.14091 (13) | 0.1149 (3) | 0.26188 (16) | 0.0505 (8) | |
H20 | 0.1577 | 0.0417 | 0.2503 | 0.061* | |
C21 | 0.09421 (14) | 0.1002 (4) | 0.27935 (18) | 0.0600 (9) | |
H21 | 0.0794 | 0.0159 | 0.2796 | 0.072* | |
C22 | 0.06937 (14) | 0.2092 (4) | 0.29636 (17) | 0.0603 (9) | |
H22 | 0.0388 | 0.1972 | 0.3094 | 0.072* | |
C23 | 0.08950 (12) | 0.3358 (3) | 0.29424 (16) | 0.0512 (8) | |
H23 | 0.0715 | 0.4092 | 0.3036 | 0.061* | |
C24 | 0.13639 (11) | 0.3526 (3) | 0.27808 (13) | 0.0386 (7) | |
C25 | 0.07596 (15) | 0.5630 (4) | 0.18071 (17) | 0.0623 (10) | |
C26 | 0.05725 (14) | 0.4628 (3) | 0.12536 (16) | 0.0554 (9) | |
C27 | 0.09256 (15) | 0.3970 (4) | 0.10118 (17) | 0.0606 (9) | |
H27 | 0.1310 | 0.4133 | 0.1212 | 0.073* | |
C28 | 0.07296 (16) | 0.3063 (4) | 0.04756 (19) | 0.0679 (10) | |
H28 | 0.0980 | 0.2623 | 0.0324 | 0.081* | |
C29 | 0.01600 (17) | 0.2825 (4) | 0.0172 (2) | 0.0710 (10) | |
C30 | −0.01998 (18) | 0.3488 (4) | 0.0409 (2) | 0.0793 (12) | |
H30 | −0.0584 | 0.3330 | 0.0207 | 0.095* | |
C31 | −0.00027 (15) | 0.4375 (4) | 0.0938 (2) | 0.0699 (11) | |
H31 | −0.0254 | 0.4814 | 0.1089 | 0.084* | |
C32 | 0.22156 (18) | 0.7884 (3) | 0.37160 (19) | 0.0694 (11) | |
H32A | 0.1913 | 0.8013 | 0.3874 | 0.104* | |
H32B | 0.2294 | 0.8706 | 0.3538 | 0.104* | |
H32C | 0.2545 | 0.7595 | 0.4090 | 0.104* | |
O33 | −0.00877 (13) | 0.1998 (3) | −0.03640 (16) | 0.1022 (10) | |
O34 | 0.11676 (11) | 0.6028 (2) | 0.37120 (13) | 0.0700 (7) | |
O35 | 0.24728 (9) | 0.4777 (2) | 0.23240 (10) | 0.0505 (6) | |
O36 | 0.04163 (12) | 0.6258 (4) | 0.19511 (16) | 0.1074 (12) | |
O37 | 0.0000 | 0.8415 (5) | 0.2500 | 0.140 (2) | |
H37 | 0.019 (2) | 0.7908 (18) | 0.233 (3) | 0.168* | |
C38 | 0.0251 (2) | 0.1418 (6) | −0.0689 (3) | 0.124 (2) | |
H38A | 0.0446 | 0.2106 | −0.0827 | 0.186* | |
H38B | 0.0017 | 0.0929 | −0.1084 | 0.186* | |
H38C | 0.0519 | 0.0827 | −0.0377 | 0.186* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0725 (18) | 0.0298 (13) | 0.0447 (14) | 0.0024 (12) | 0.0249 (13) | −0.0010 (11) |
C2 | 0.0519 (17) | 0.0340 (16) | 0.0381 (15) | 0.0014 (13) | 0.0198 (13) | 0.0004 (12) |
C3 | 0.0420 (16) | 0.0359 (15) | 0.0337 (14) | 0.0042 (12) | 0.0113 (12) | 0.0022 (12) |
C4 | 0.061 (2) | 0.0435 (18) | 0.0484 (18) | 0.0140 (15) | 0.0213 (16) | 0.0096 (14) |
C5 | 0.082 (2) | 0.0392 (18) | 0.058 (2) | 0.0150 (16) | 0.0306 (19) | 0.0091 (15) |
C6 | 0.060 (2) | 0.0400 (17) | 0.0522 (19) | −0.0028 (15) | 0.0280 (16) | −0.0084 (14) |
C7 | 0.079 (2) | 0.0373 (17) | 0.0410 (17) | −0.0123 (15) | 0.0297 (16) | −0.0077 (13) |
C8 | 0.109 (3) | 0.057 (2) | 0.054 (2) | −0.024 (2) | 0.045 (2) | −0.0150 (18) |
C9 | 0.148 (4) | 0.065 (3) | 0.041 (2) | −0.035 (3) | 0.044 (3) | −0.0089 (18) |
C10 | 0.128 (4) | 0.057 (2) | 0.038 (2) | −0.024 (2) | 0.012 (2) | −0.0010 (16) |
C11 | 0.080 (3) | 0.0431 (19) | 0.0400 (18) | −0.0143 (18) | 0.0027 (17) | −0.0036 (14) |
C12 | 0.073 (3) | 0.064 (2) | 0.061 (3) | −0.002 (2) | −0.014 (2) | −0.0020 (19) |
C13 | 0.053 (2) | 0.079 (3) | 0.069 (3) | −0.0020 (19) | 0.0041 (19) | −0.009 (2) |
C14 | 0.050 (2) | 0.065 (2) | 0.055 (2) | −0.0023 (17) | 0.0156 (16) | 0.0016 (17) |
C15 | 0.0543 (19) | 0.0343 (16) | 0.0397 (16) | −0.0065 (13) | 0.0139 (14) | −0.0028 (12) |
C16 | 0.068 (2) | 0.0337 (16) | 0.0399 (17) | −0.0122 (15) | 0.0170 (15) | −0.0064 (13) |
C17 | 0.0453 (16) | 0.0371 (16) | 0.0328 (14) | 0.0003 (13) | 0.0155 (13) | −0.0004 (12) |
N18 | 0.0447 (14) | 0.0347 (14) | 0.0458 (14) | 0.0039 (11) | 0.0200 (11) | −0.0029 (11) |
C19 | 0.0414 (16) | 0.0385 (16) | 0.0342 (15) | −0.0013 (13) | 0.0088 (13) | 0.0018 (12) |
C20 | 0.0549 (19) | 0.0427 (18) | 0.0497 (18) | −0.0040 (15) | 0.0149 (15) | −0.0031 (14) |
C21 | 0.057 (2) | 0.058 (2) | 0.059 (2) | −0.0210 (18) | 0.0154 (17) | −0.0033 (17) |
C22 | 0.0390 (18) | 0.085 (3) | 0.055 (2) | −0.0136 (18) | 0.0152 (15) | 0.0020 (18) |
C23 | 0.0401 (17) | 0.062 (2) | 0.0496 (18) | 0.0001 (15) | 0.0151 (14) | −0.0028 (15) |
C24 | 0.0372 (15) | 0.0440 (17) | 0.0324 (14) | 0.0002 (13) | 0.0104 (12) | 0.0038 (12) |
C25 | 0.063 (2) | 0.073 (2) | 0.051 (2) | 0.0314 (19) | 0.0211 (17) | 0.0148 (17) |
C26 | 0.059 (2) | 0.064 (2) | 0.0418 (18) | 0.0179 (17) | 0.0164 (16) | 0.0126 (16) |
C27 | 0.0499 (19) | 0.074 (2) | 0.048 (2) | 0.0102 (17) | 0.0074 (16) | 0.0100 (18) |
C28 | 0.067 (2) | 0.074 (3) | 0.057 (2) | 0.015 (2) | 0.0162 (19) | 0.0036 (19) |
C29 | 0.071 (3) | 0.067 (3) | 0.065 (2) | 0.000 (2) | 0.013 (2) | 0.003 (2) |
C30 | 0.062 (2) | 0.085 (3) | 0.083 (3) | −0.011 (2) | 0.018 (2) | 0.006 (2) |
C31 | 0.059 (2) | 0.081 (3) | 0.074 (3) | 0.010 (2) | 0.029 (2) | 0.017 (2) |
C32 | 0.114 (3) | 0.0390 (19) | 0.067 (2) | −0.0136 (19) | 0.047 (2) | −0.0108 (16) |
O33 | 0.092 (2) | 0.093 (2) | 0.093 (2) | −0.0087 (18) | 0.0018 (18) | −0.0276 (18) |
O34 | 0.0721 (17) | 0.0713 (17) | 0.0801 (18) | 0.0110 (14) | 0.0440 (14) | −0.0008 (14) |
O35 | 0.0614 (13) | 0.0462 (13) | 0.0550 (13) | −0.0087 (10) | 0.0345 (11) | −0.0035 (10) |
O36 | 0.0766 (19) | 0.148 (3) | 0.085 (2) | 0.0525 (19) | 0.0152 (16) | −0.0241 (19) |
O37 | 0.168 (6) | 0.095 (4) | 0.197 (6) | 0.000 | 0.115 (5) | 0.000 |
C38 | 0.129 (4) | 0.119 (4) | 0.093 (4) | 0.031 (3) | 0.005 (3) | −0.039 (3) |
Geometric parameters (Å, º) top
N1—C5 | 1.467 (4) | C17—N18 | 1.350 (3) |
N1—C2 | 1.468 (4) | N18—C19 | 1.407 (4) |
N1—C32 | 1.470 (4) | N18—H18 | 0.8600 |
C2—C15 | 1.529 (4) | C19—C20 | 1.369 (4) |
C2—C6 | 1.573 (4) | C19—C24 | 1.397 (4) |
C2—C3 | 1.578 (4) | C20—C21 | 1.386 (5) |
C3—C24 | 1.516 (4) | C20—H20 | 0.9300 |
C3—C17 | 1.538 (4) | C21—C22 | 1.381 (5) |
C3—C4 | 1.578 (4) | C21—H21 | 0.9300 |
C4—C25 | 1.500 (5) | C22—C23 | 1.381 (5) |
C4—C5 | 1.525 (4) | C22—H22 | 0.9300 |
C4—H4 | 0.9800 | C23—C24 | 1.377 (4) |
C5—H5A | 0.9700 | C23—H23 | 0.9300 |
C5—H5B | 0.9700 | C25—O36 | 1.211 (4) |
C6—O34 | 1.213 (4) | C25—C26 | 1.479 (5) |
C6—C7 | 1.467 (4) | C26—C27 | 1.365 (5) |
C7—C8 | 1.384 (4) | C26—C31 | 1.397 (5) |
C7—C16 | 1.387 (4) | C27—C28 | 1.392 (5) |
C8—C9 | 1.405 (6) | C27—H27 | 0.9300 |
C8—H8 | 0.9300 | C28—C29 | 1.379 (5) |
C9—C10 | 1.350 (6) | C28—H28 | 0.9300 |
C9—H9 | 0.9300 | C29—O33 | 1.355 (4) |
C10—C11 | 1.410 (6) | C29—C30 | 1.375 (6) |
C10—H10 | 0.9300 | C30—C31 | 1.369 (6) |
C11—C12 | 1.392 (6) | C30—H30 | 0.9300 |
C11—C16 | 1.402 (4) | C31—H31 | 0.9300 |
C12—C13 | 1.363 (6) | C32—H32A | 0.9600 |
C12—H12 | 0.9300 | C32—H32B | 0.9600 |
C13—C14 | 1.413 (5) | C32—H32C | 0.9600 |
C13—H13 | 0.9300 | O33—C38 | 1.418 (6) |
C14—C15 | 1.362 (4) | C38—H38A | 0.9600 |
C14—H14 | 0.9300 | C38—H38B | 0.9600 |
C15—C16 | 1.411 (4) | C38—H38C | 0.9600 |
C17—O35 | 1.221 (3) | | |
| | | |
C5—N1—C2 | 105.9 (2) | C11—C16—C15 | 123.3 (3) |
C5—N1—C32 | 113.4 (3) | O35—C17—N18 | 126.5 (3) |
C2—N1—C32 | 113.8 (2) | O35—C17—C3 | 124.9 (3) |
N1—C2—C15 | 112.2 (2) | N18—C17—C3 | 108.6 (2) |
N1—C2—C6 | 112.9 (2) | C17—N18—C19 | 111.6 (2) |
C15—C2—C6 | 101.7 (2) | C17—N18—H18 | 124.2 |
N1—C2—C3 | 102.6 (2) | C19—N18—H18 | 124.2 |
C15—C2—C3 | 116.6 (2) | C20—C19—C24 | 122.3 (3) |
C6—C2—C3 | 111.4 (2) | C20—C19—N18 | 128.2 (3) |
C24—C3—C17 | 101.8 (2) | C24—C19—N18 | 109.4 (2) |
C24—C3—C4 | 118.5 (2) | C19—C20—C21 | 117.7 (3) |
C17—C3—C4 | 107.9 (2) | C19—C20—H20 | 121.1 |
C24—C3—C2 | 115.2 (2) | C21—C20—H20 | 121.1 |
C17—C3—C2 | 109.6 (2) | C22—C21—C20 | 120.9 (3) |
C4—C3—C2 | 103.6 (2) | C22—C21—H21 | 119.6 |
C25—C4—C5 | 116.2 (3) | C20—C21—H21 | 119.6 |
C25—C4—C3 | 115.7 (3) | C21—C22—C23 | 120.6 (3) |
C5—C4—C3 | 105.0 (2) | C21—C22—H22 | 119.7 |
C25—C4—H4 | 106.4 | C23—C22—H22 | 119.7 |
C5—C4—H4 | 106.4 | C24—C23—C22 | 119.5 (3) |
C3—C4—H4 | 106.4 | C24—C23—H23 | 120.2 |
N1—C5—C4 | 104.4 (2) | C22—C23—H23 | 120.2 |
N1—C5—H5A | 110.9 | C23—C24—C19 | 118.9 (3) |
C4—C5—H5A | 110.9 | C23—C24—C3 | 132.7 (3) |
N1—C5—H5B | 110.9 | C19—C24—C3 | 108.5 (2) |
C4—C5—H5B | 110.9 | O36—C25—C26 | 120.1 (3) |
H5A—C5—H5B | 108.9 | O36—C25—C4 | 119.2 (3) |
O34—C6—C7 | 127.8 (3) | C26—C25—C4 | 120.8 (3) |
O34—C6—C2 | 124.1 (3) | C27—C26—C31 | 117.6 (3) |
C7—C6—C2 | 107.9 (3) | C27—C26—C25 | 124.0 (3) |
C8—C7—C16 | 119.6 (3) | C31—C26—C25 | 118.3 (3) |
C8—C7—C6 | 132.3 (3) | C26—C27—C28 | 122.1 (3) |
C16—C7—C6 | 108.0 (3) | C26—C27—H27 | 118.9 |
C7—C8—C9 | 117.7 (4) | C28—C27—H27 | 118.9 |
C7—C8—H8 | 121.2 | C29—C28—C27 | 119.3 (4) |
C9—C8—H8 | 121.2 | C29—C28—H28 | 120.4 |
C10—C9—C8 | 122.4 (4) | C27—C28—H28 | 120.4 |
C10—C9—H9 | 118.8 | O33—C29—C30 | 115.6 (4) |
C8—C9—H9 | 118.8 | O33—C29—C28 | 125.4 (4) |
C9—C10—C11 | 121.6 (4) | C30—C29—C28 | 119.1 (4) |
C9—C10—H10 | 119.2 | C31—C30—C29 | 121.2 (4) |
C11—C10—H10 | 119.2 | C31—C30—H30 | 119.4 |
C12—C11—C16 | 117.0 (3) | C29—C30—H30 | 119.4 |
C12—C11—C10 | 127.5 (4) | C30—C31—C26 | 120.6 (4) |
C16—C11—C10 | 115.5 (4) | C30—C31—H31 | 119.7 |
C13—C12—C11 | 120.1 (3) | C26—C31—H31 | 119.7 |
C13—C12—H12 | 119.9 | N1—C32—H32A | 109.5 |
C11—C12—H12 | 119.9 | N1—C32—H32B | 109.5 |
C12—C13—C14 | 122.4 (4) | H32A—C32—H32B | 109.5 |
C12—C13—H13 | 118.8 | N1—C32—H32C | 109.5 |
C14—C13—H13 | 118.8 | H32A—C32—H32C | 109.5 |
C15—C14—C13 | 119.2 (3) | H32B—C32—H32C | 109.5 |
C15—C14—H14 | 120.4 | C29—O33—C38 | 118.4 (4) |
C13—C14—H14 | 120.4 | O33—C38—H38A | 109.5 |
C14—C15—C16 | 117.9 (3) | O33—C38—H38B | 109.5 |
C14—C15—C2 | 133.3 (3) | H38A—C38—H38B | 109.5 |
C16—C15—C2 | 108.7 (3) | O33—C38—H38C | 109.5 |
C7—C16—C11 | 123.2 (3) | H38A—C38—H38C | 109.5 |
C7—C16—C15 | 113.4 (3) | H38B—C38—H38C | 109.5 |
| | | |
C5—N1—C2—C15 | 168.3 (2) | C6—C7—C16—C15 | −1.6 (3) |
C32—N1—C2—C15 | −66.4 (3) | C12—C11—C16—C7 | −175.9 (3) |
C5—N1—C2—C6 | −77.5 (3) | C10—C11—C16—C7 | 3.4 (4) |
C32—N1—C2—C6 | 47.7 (4) | C12—C11—C16—C15 | 0.5 (5) |
C5—N1—C2—C3 | 42.5 (3) | C10—C11—C16—C15 | 179.8 (3) |
C32—N1—C2—C3 | 167.7 (3) | C14—C15—C16—C7 | 175.2 (3) |
N1—C2—C3—C24 | −156.9 (2) | C2—C15—C16—C7 | −1.8 (3) |
C15—C2—C3—C24 | 80.1 (3) | C14—C15—C16—C11 | −1.5 (4) |
C6—C2—C3—C24 | −35.9 (3) | C2—C15—C16—C11 | −178.6 (3) |
N1—C2—C3—C17 | 89.1 (2) | C24—C3—C17—O35 | 174.3 (3) |
C15—C2—C3—C17 | −33.9 (3) | C4—C3—C17—O35 | 48.9 (4) |
C6—C2—C3—C17 | −149.9 (2) | C2—C3—C17—O35 | −63.3 (3) |
N1—C2—C3—C4 | −25.8 (3) | C24—C3—C17—N18 | −3.8 (3) |
C15—C2—C3—C4 | −148.8 (2) | C4—C3—C17—N18 | −129.3 (2) |
C6—C2—C3—C4 | 95.2 (3) | C2—C3—C17—N18 | 118.6 (2) |
C24—C3—C4—C25 | 1.1 (4) | O35—C17—N18—C19 | −174.1 (3) |
C17—C3—C4—C25 | 115.9 (3) | C3—C17—N18—C19 | 4.0 (3) |
C2—C3—C4—C25 | −128.0 (3) | C17—N18—C19—C20 | 176.4 (3) |
C24—C3—C4—C5 | 130.5 (3) | C17—N18—C19—C24 | −2.5 (3) |
C17—C3—C4—C5 | −114.7 (3) | C24—C19—C20—C21 | −1.3 (4) |
C2—C3—C4—C5 | 1.4 (3) | N18—C19—C20—C21 | 179.9 (3) |
C2—N1—C5—C4 | −42.3 (3) | C19—C20—C21—C22 | 0.1 (5) |
C32—N1—C5—C4 | −167.7 (3) | C20—C21—C22—C23 | 2.1 (5) |
C25—C4—C5—N1 | 152.8 (3) | C21—C22—C23—C24 | −3.1 (5) |
C3—C4—C5—N1 | 23.7 (3) | C22—C23—C24—C19 | 1.9 (4) |
N1—C2—C6—O34 | 50.7 (4) | C22—C23—C24—C3 | −178.9 (3) |
C15—C2—C6—O34 | 171.1 (3) | C20—C19—C24—C23 | 0.3 (4) |
C3—C2—C6—O34 | −64.0 (4) | N18—C19—C24—C23 | 179.3 (2) |
N1—C2—C6—C7 | −125.4 (3) | C20—C19—C24—C3 | −179.1 (3) |
C15—C2—C6—C7 | −5.0 (3) | N18—C19—C24—C3 | −0.1 (3) |
C3—C2—C6—C7 | 119.9 (2) | C17—C3—C24—C23 | −177.0 (3) |
O34—C6—C7—C8 | 5.6 (6) | C4—C3—C24—C23 | −58.9 (4) |
C2—C6—C7—C8 | −178.4 (3) | C2—C3—C24—C23 | 64.6 (4) |
O34—C6—C7—C16 | −171.7 (3) | C17—C3—C24—C19 | 2.3 (3) |
C2—C6—C7—C16 | 4.2 (3) | C4—C3—C24—C19 | 120.4 (3) |
C16—C7—C8—C9 | −0.1 (5) | C2—C3—C24—C19 | −116.1 (3) |
C6—C7—C8—C9 | −177.2 (3) | C5—C4—C25—O36 | −17.5 (5) |
C7—C8—C9—C10 | 1.8 (5) | C3—C4—C25—O36 | 106.3 (4) |
C8—C9—C10—C11 | −1.0 (6) | C5—C4—C25—C26 | 163.2 (3) |
C9—C10—C11—C12 | 177.6 (4) | C3—C4—C25—C26 | −73.0 (4) |
C9—C10—C11—C16 | −1.6 (5) | O36—C25—C26—C27 | 173.3 (4) |
C16—C11—C12—C13 | 0.2 (5) | C4—C25—C26—C27 | −7.4 (5) |
C10—C11—C12—C13 | −178.9 (3) | O36—C25—C26—C31 | −4.0 (5) |
C11—C12—C13—C14 | 0.0 (6) | C4—C25—C26—C31 | 175.3 (3) |
C12—C13—C14—C15 | −1.0 (6) | C31—C26—C27—C28 | −0.7 (5) |
C13—C14—C15—C16 | 1.7 (5) | C25—C26—C27—C28 | −178.0 (3) |
C13—C14—C15—C2 | 177.8 (3) | C26—C27—C28—C29 | 0.6 (5) |
N1—C2—C15—C14 | −51.4 (4) | C27—C28—C29—O33 | 178.1 (4) |
C6—C2—C15—C14 | −172.3 (3) | C27—C28—C29—C30 | −0.2 (6) |
C3—C2—C15—C14 | 66.4 (4) | O33—C29—C30—C31 | −178.4 (4) |
N1—C2—C15—C16 | 125.0 (2) | C28—C29—C30—C31 | 0.1 (6) |
C6—C2—C15—C16 | 4.1 (3) | C29—C30—C31—C26 | −0.2 (6) |
C3—C2—C15—C16 | −117.2 (3) | C27—C26—C31—C30 | 0.6 (5) |
C8—C7—C16—C11 | −2.6 (5) | C25—C26—C31—C30 | 178.0 (3) |
C6—C7—C16—C11 | 175.2 (3) | C30—C29—O33—C38 | 172.0 (4) |
C8—C7—C16—C15 | −179.3 (3) | C28—C29—O33—C38 | −6.4 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O35 | 0.98 | 2.48 | 2.947 (4) | 109 |
C5—H5B···O34 | 0.97 | 2.45 | 3.017 (4) | 116 |
C5—H5B···O36 | 0.97 | 2.46 | 2.804 (5) | 100 |
C14—H14···O35 | 0.93 | 2.40 | 3.038 (4) | 125 |
C23—H23···O34 | 0.93 | 2.43 | 3.079 (4) | 126 |
O37—H37···O36 | 0.87 (5) | 2.02 (4) | 2.848 (5) | 159 (4) |
N18—H18···N1i | 0.86 | 2.38 | 3.146 (3) | 148 |
C20—H20···O35i | 0.93 | 2.41 | 3.143 (4) | 135 |
C21—H21···O37ii | 0.93 | 2.58 | 3.445 (5) | 154 |
C32—H32B···O35iii | 0.96 | 2.37 | 3.222 (4) | 147 |
N18—H18···O35i | 0.86 | 2.59 | 3.225 (3) | 131 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) −x+1/2, y+1/2, −z+1/2. |