The title compound, C
16H
11NO
3, contains two planar ring systems and, in the crystal structure, the asymmetric unit is composed of two molecules. There are some intermolecular C—H
O hydrogen bonds and π–π stacking interactions.
Supporting information
CCDC reference: 238830
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.051
- wR factor = 0.127
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT707_ALERT_1_A D...A Calc 17.948(2), Rep 3.451(2), Dev.. 7248.50 Sigma
C9 -O1 1.555 3.666
PLAT707_ALERT_1_A D...A Calc 18.330(2), Rep 3.506(2), Dev.. 7412.00 Sigma
C9 -O4 1.555 1.555
PLAT707_ALERT_1_A D...A Calc 17.139(3), Rep 3.206(3), Dev.. 4644.33 Sigma
C14 -O6 1.555 4.564
PLAT707_ALERT_1_A D...A Calc 22.840(3), Rep 3.214(3), Dev.. 6542.00 Sigma
C30 -O3 1.555 4.555
PLAT726_ALERT_1_A H...A Calc 18.56750, Rep 2.59000 Dev... 15.98 Ang.
H9A -O1 1.555 3.666
PLAT726_ALERT_1_A H...A Calc 18.61590, Rep 2.56000 Dev... 16.06 Ang.
H9B -O4 1.555 1.555
PLAT726_ALERT_1_A H...A Calc 17.88460, Rep 2.59000 Dev... 15.29 Ang.
H14 -O6 1.555 4.564
PLAT726_ALERT_1_A H...A Calc 22.15000, Rep 2.57000 Dev... 19.58 Ang.
H30 -O3 1.555 4.555
PLAT728_ALERT_1_A D-H..A Calc 49.14, Rep 147.00 Dev... 97.86 Deg.
C9 -H9A -O1 1.555 1.555 3.666
PLAT728_ALERT_1_A D-H..A Calc 71.39, Rep 165.00 Dev... 93.61 Deg.
C9 -H9B -O4 1.555 1.555 1.555
PLAT728_ALERT_1_A D-H..A Calc 35.87, Rep 124.00 Dev... 88.13 Deg.
C14 -H14 -O6 1.555 1.555 4.564
PLAT728_ALERT_1_A D-H..A Calc 137.08, Rep 127.00 Dev... 10.08 Deg.
C30 -H30 -O3 1.555 1.555 4.555
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for C14 - C15 .. 5.57 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C26 - C27 .. 5.03 su
12 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
12 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 2002); software used to prepare material for publication: SHELXL97.
1-phenyl-2-phthalimidoethanone
top
Crystal data top
C16H11NO3 | F(000) = 1104 |
Mr = 265.26 | Dx = 1.356 Mg m−3 |
Monoclinic, P21/c | Melting point: 446 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 12.8670 (5) Å | Cell parameters from 648 reflections |
b = 14.2568 (6) Å | θ = 2.5–23.5° |
c = 14.2196 (6) Å | µ = 0.10 mm−1 |
β = 94.728 (2)° | T = 298 K |
V = 2599.60 (18) Å3 | Block, colorless |
Z = 8 | 0.39 × 0.35 × 0.32 mm |
Data collection top
Bruker SMART APEX area-detector diffractometer | 4665 independent reflections |
Radiation source: fine-focus sealed tube | 3520 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 25.2°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −15→15 |
Tmin = 0.963, Tmax = 0.974 | k = −17→12 |
13485 measured reflections | l = −17→16 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0636P)2 + 0.3423P] where P = (Fo2 + 2Fc2)/3 |
4665 reflections | (Δ/σ)max < 0.001 |
361 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.24 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 | |
O1 | 0.51631 (11) | 0.86804 (10) | 0.03907 (11) | 0.0728 (4) | |
O2 | 0.86323 (11) | 0.88937 (10) | 0.12847 (11) | 0.0713 (4) | |
O3 | 0.61001 (13) | 0.99092 (11) | 0.23022 (10) | 0.0839 (5) | |
O4 | 0.89942 (10) | 0.12473 (9) | 1.01796 (8) | 0.0597 (4) | |
O5 | 0.90628 (11) | 0.12087 (10) | 0.69854 (8) | 0.0627 (4) | |
O6 | 0.71791 (10) | 0.01113 (9) | 0.86403 (10) | 0.0673 (4) | |
N1 | 0.68809 (11) | 0.90227 (10) | 0.08326 (10) | 0.0508 (4) | |
N2 | 0.90024 (11) | 0.09980 (10) | 0.85838 (9) | 0.0468 (4) | |
C1 | 0.75111 (14) | 0.75244 (13) | 0.10202 (11) | 0.0492 (5) | |
C2 | 0.81148 (17) | 0.67303 (15) | 0.11784 (13) | 0.0616 (5) | |
H2 | 0.8825 | 0.6772 | 0.1355 | 0.074* | |
C3 | 0.7623 (2) | 0.58692 (15) | 0.10646 (14) | 0.0729 (6) | |
H3 | 0.8008 | 0.5322 | 0.1170 | 0.088* | |
C4 | 0.6569 (2) | 0.58116 (16) | 0.07966 (16) | 0.0792 (7) | |
H4 | 0.6257 | 0.5225 | 0.0725 | 0.095* | |
C5 | 0.59685 (18) | 0.66089 (15) | 0.06329 (15) | 0.0693 (6) | |
H5 | 0.5260 | 0.6568 | 0.0448 | 0.083* | |
C6 | 0.64549 (15) | 0.74605 (13) | 0.07530 (12) | 0.0512 (5) | |
C7 | 0.60365 (15) | 0.84237 (13) | 0.06299 (12) | 0.0526 (5) | |
C8 | 0.77938 (15) | 0.85352 (13) | 0.10808 (12) | 0.0506 (5) | |
C9 | 0.67890 (15) | 1.00328 (12) | 0.08164 (13) | 0.0532 (5) | |
H9A | 0.6321 | 1.0216 | 0.0278 | 0.064* | |
H9B | 0.7467 | 1.0304 | 0.0736 | 0.064* | |
C10 | 0.63858 (14) | 1.04269 (14) | 0.17023 (13) | 0.0544 (5) | |
C11 | 0.63689 (13) | 1.14659 (14) | 0.18053 (13) | 0.0530 (5) | |
C12 | 0.65836 (15) | 1.20681 (14) | 0.10846 (15) | 0.0601 (5) | |
H12 | 0.6735 | 1.1825 | 0.0504 | 0.072* | |
C13 | 0.65751 (18) | 1.30243 (15) | 0.12183 (18) | 0.0750 (6) | |
H13 | 0.6717 | 1.3421 | 0.0726 | 0.090* | |
C14 | 0.63607 (18) | 1.33956 (18) | 0.2064 (2) | 0.0830 (7) | |
H14 | 0.6354 | 1.4043 | 0.2146 | 0.100* | |
C15 | 0.61558 (18) | 1.28161 (19) | 0.2789 (2) | 0.0850 (8) | |
H15 | 0.6017 | 1.3069 | 0.3369 | 0.102* | |
C16 | 0.61545 (16) | 1.18453 (17) | 0.26654 (16) | 0.0724 (6) | |
H16 | 0.6010 | 1.1453 | 0.3160 | 0.087* | |
C17 | 0.89447 (15) | 0.33605 (13) | 0.95477 (13) | 0.0567 (5) | |
H17 | 0.8936 | 0.3363 | 1.0201 | 0.068* | |
C18 | 0.89316 (16) | 0.41883 (14) | 0.90369 (15) | 0.0639 (5) | |
H18 | 0.8917 | 0.4758 | 0.9353 | 0.077* | |
C19 | 0.89392 (15) | 0.41825 (14) | 0.80626 (15) | 0.0603 (5) | |
H19 | 0.8926 | 0.4748 | 0.7736 | 0.072* | |
C20 | 0.89657 (13) | 0.33468 (14) | 0.75667 (13) | 0.0521 (5) | |
H20 | 0.8969 | 0.3341 | 0.6913 | 0.063* | |
C21 | 0.89867 (13) | 0.25249 (12) | 0.80773 (11) | 0.0437 (4) | |
C22 | 0.89703 (13) | 0.25338 (12) | 0.90513 (12) | 0.0449 (4) | |
C23 | 0.89870 (13) | 0.15471 (13) | 0.93811 (12) | 0.0453 (4) | |
C24 | 0.90200 (13) | 0.15316 (13) | 0.77681 (12) | 0.0462 (4) | |
C25 | 0.90055 (14) | −0.00125 (13) | 0.86034 (13) | 0.0523 (5) | |
H25A | 0.9427 | −0.0225 | 0.9159 | 0.063* | |
H25B | 0.9321 | −0.0247 | 0.8053 | 0.063* | |
C26 | 0.79128 (14) | −0.04136 (13) | 0.86161 (11) | 0.0469 (4) | |
C27 | 0.77879 (13) | −0.14473 (12) | 0.85838 (11) | 0.0452 (4) | |
C28 | 0.86258 (15) | −0.20576 (13) | 0.87283 (12) | 0.0515 (5) | |
H28 | 0.9295 | −0.1820 | 0.8860 | 0.062* | |
C29 | 0.84737 (17) | −0.30123 (14) | 0.86774 (13) | 0.0616 (5) | |
H29 | 0.9041 | −0.3415 | 0.8778 | 0.074* | |
C30 | 0.74959 (18) | −0.33732 (15) | 0.84803 (13) | 0.0652 (6) | |
H30 | 0.7398 | −0.4019 | 0.8447 | 0.078* | |
C31 | 0.66597 (18) | −0.27805 (16) | 0.83320 (14) | 0.0661 (6) | |
H31 | 0.5995 | −0.3027 | 0.8193 | 0.079* | |
C32 | 0.67952 (15) | −0.18222 (15) | 0.83867 (12) | 0.0570 (5) | |
H32 | 0.6222 | −0.1426 | 0.8292 | 0.068* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0536 (9) | 0.0725 (10) | 0.0898 (10) | 0.0039 (7) | −0.0099 (7) | 0.0075 (8) |
O2 | 0.0514 (9) | 0.0699 (10) | 0.0913 (11) | −0.0044 (7) | −0.0012 (7) | −0.0012 (8) |
O3 | 0.1150 (13) | 0.0699 (10) | 0.0708 (9) | 0.0123 (9) | 0.0315 (9) | 0.0165 (8) |
O4 | 0.0730 (9) | 0.0625 (9) | 0.0429 (7) | −0.0034 (7) | 0.0014 (6) | 0.0110 (6) |
O5 | 0.0745 (9) | 0.0699 (9) | 0.0438 (7) | −0.0018 (7) | 0.0046 (6) | −0.0078 (7) |
O6 | 0.0562 (8) | 0.0581 (9) | 0.0883 (10) | 0.0100 (7) | 0.0102 (7) | 0.0089 (7) |
N1 | 0.0497 (9) | 0.0454 (9) | 0.0569 (9) | 0.0026 (7) | 0.0022 (7) | 0.0015 (7) |
N2 | 0.0514 (9) | 0.0440 (9) | 0.0445 (8) | −0.0015 (7) | 0.0015 (6) | 0.0008 (7) |
C1 | 0.0590 (12) | 0.0515 (12) | 0.0377 (9) | 0.0054 (9) | 0.0070 (8) | 0.0019 (8) |
C2 | 0.0708 (13) | 0.0628 (14) | 0.0516 (11) | 0.0146 (11) | 0.0066 (9) | 0.0051 (10) |
C3 | 0.109 (2) | 0.0507 (13) | 0.0597 (13) | 0.0173 (13) | 0.0086 (12) | 0.0055 (10) |
C4 | 0.116 (2) | 0.0481 (13) | 0.0729 (15) | −0.0098 (13) | 0.0035 (14) | 0.0018 (11) |
C5 | 0.0788 (15) | 0.0555 (14) | 0.0725 (14) | −0.0099 (11) | −0.0015 (11) | 0.0051 (11) |
C6 | 0.0599 (12) | 0.0491 (12) | 0.0446 (10) | −0.0003 (9) | 0.0034 (8) | 0.0026 (8) |
C7 | 0.0526 (12) | 0.0559 (12) | 0.0487 (10) | 0.0003 (9) | 0.0006 (8) | 0.0031 (9) |
C8 | 0.0501 (11) | 0.0557 (12) | 0.0464 (10) | 0.0031 (9) | 0.0058 (8) | −0.0006 (9) |
C9 | 0.0572 (11) | 0.0452 (11) | 0.0572 (11) | 0.0020 (9) | 0.0056 (9) | 0.0023 (9) |
C10 | 0.0531 (11) | 0.0576 (13) | 0.0524 (11) | 0.0078 (9) | 0.0042 (9) | 0.0055 (10) |
C11 | 0.0425 (10) | 0.0586 (13) | 0.0571 (11) | 0.0063 (9) | −0.0017 (8) | −0.0074 (10) |
C12 | 0.0629 (13) | 0.0530 (13) | 0.0626 (12) | 0.0009 (10) | −0.0046 (10) | −0.0059 (10) |
C13 | 0.0772 (15) | 0.0559 (14) | 0.0894 (17) | −0.0031 (12) | −0.0089 (12) | −0.0031 (13) |
C14 | 0.0734 (16) | 0.0643 (16) | 0.108 (2) | 0.0039 (12) | −0.0104 (14) | −0.0227 (16) |
C15 | 0.0716 (16) | 0.092 (2) | 0.0911 (18) | 0.0108 (14) | 0.0060 (13) | −0.0423 (16) |
C16 | 0.0666 (14) | 0.0807 (17) | 0.0708 (14) | 0.0090 (12) | 0.0109 (11) | −0.0124 (12) |
C17 | 0.0671 (13) | 0.0548 (12) | 0.0479 (10) | −0.0013 (10) | 0.0033 (9) | −0.0016 (9) |
C18 | 0.0730 (14) | 0.0483 (12) | 0.0706 (14) | −0.0007 (10) | 0.0069 (11) | −0.0038 (10) |
C19 | 0.0597 (12) | 0.0488 (12) | 0.0725 (14) | 0.0004 (9) | 0.0059 (10) | 0.0158 (10) |
C20 | 0.0490 (11) | 0.0614 (13) | 0.0458 (10) | −0.0003 (9) | 0.0036 (8) | 0.0104 (9) |
C21 | 0.0395 (9) | 0.0499 (11) | 0.0413 (9) | −0.0007 (8) | 0.0009 (7) | 0.0046 (8) |
C22 | 0.0441 (10) | 0.0486 (11) | 0.0419 (9) | −0.0015 (8) | 0.0023 (7) | 0.0026 (8) |
C23 | 0.0429 (10) | 0.0518 (11) | 0.0406 (10) | −0.0029 (8) | 0.0000 (7) | 0.0051 (8) |
C24 | 0.0414 (10) | 0.0573 (12) | 0.0396 (10) | −0.0028 (8) | 0.0006 (7) | 0.0009 (8) |
C25 | 0.0527 (11) | 0.0452 (11) | 0.0584 (11) | 0.0013 (8) | 0.0011 (8) | 0.0000 (9) |
C26 | 0.0491 (10) | 0.0549 (12) | 0.0365 (9) | 0.0041 (9) | 0.0032 (7) | 0.0054 (8) |
C27 | 0.0505 (10) | 0.0493 (11) | 0.0359 (9) | −0.0025 (8) | 0.0035 (7) | 0.0024 (8) |
C28 | 0.0521 (11) | 0.0508 (12) | 0.0511 (10) | −0.0039 (9) | 0.0004 (8) | 0.0006 (9) |
C29 | 0.0712 (14) | 0.0511 (12) | 0.0619 (12) | 0.0027 (10) | 0.0021 (10) | −0.0009 (10) |
C30 | 0.0842 (16) | 0.0537 (13) | 0.0574 (12) | −0.0124 (12) | 0.0032 (11) | −0.0038 (10) |
C31 | 0.0650 (14) | 0.0698 (15) | 0.0627 (13) | −0.0223 (12) | 0.0002 (10) | −0.0028 (11) |
C32 | 0.0523 (11) | 0.0649 (14) | 0.0535 (11) | −0.0029 (10) | 0.0028 (9) | 0.0027 (10) |
Geometric parameters (Å, º) top
O1—C7 | 1.204 (2) | C13—H13 | 0.9300 |
O2—C8 | 1.207 (2) | C14—C15 | 1.365 (3) |
O3—C10 | 1.208 (2) | C14—H14 | 0.9300 |
O4—C23 | 1.2125 (19) | C15—C16 | 1.395 (3) |
O5—C24 | 1.210 (2) | C15—H15 | 0.9300 |
O6—C26 | 1.207 (2) | C16—H16 | 0.9300 |
N1—C8 | 1.385 (2) | C17—C22 | 1.376 (2) |
N1—C7 | 1.393 (2) | C17—C18 | 1.385 (3) |
N1—C9 | 1.445 (2) | C17—H17 | 0.9300 |
N2—C23 | 1.379 (2) | C18—C19 | 1.386 (3) |
N2—C24 | 1.389 (2) | C18—H18 | 0.9300 |
N2—C25 | 1.441 (2) | C19—C20 | 1.386 (3) |
C1—C2 | 1.381 (3) | C19—H19 | 0.9300 |
C1—C6 | 1.384 (3) | C20—C21 | 1.378 (2) |
C1—C8 | 1.487 (3) | C20—H20 | 0.9300 |
C2—C3 | 1.385 (3) | C21—C22 | 1.387 (2) |
C2—H2 | 0.9300 | C21—C24 | 1.484 (2) |
C3—C4 | 1.380 (3) | C22—C23 | 1.482 (2) |
C3—H3 | 0.9300 | C25—C26 | 1.519 (2) |
C4—C5 | 1.383 (3) | C25—H25A | 0.9700 |
C4—H4 | 0.9300 | C25—H25B | 0.9700 |
C5—C6 | 1.370 (3) | C26—C27 | 1.483 (2) |
C5—H5 | 0.9300 | C27—C28 | 1.387 (2) |
C6—C7 | 1.480 (3) | C27—C32 | 1.392 (2) |
C9—C10 | 1.510 (3) | C28—C29 | 1.376 (3) |
C9—H9A | 0.9700 | C28—H28 | 0.9300 |
C9—H9B | 0.9700 | C29—C30 | 1.367 (3) |
C10—C11 | 1.489 (3) | C29—H29 | 0.9300 |
C11—C12 | 1.382 (3) | C30—C31 | 1.371 (3) |
C11—C16 | 1.386 (3) | C30—H30 | 0.9300 |
C12—C13 | 1.377 (3) | C31—C32 | 1.379 (3) |
C12—H12 | 0.9300 | C31—H31 | 0.9300 |
C13—C14 | 1.362 (3) | C32—H32 | 0.9300 |
| | | |
C8—N1—C7 | 112.05 (15) | C11—C16—C15 | 120.0 (2) |
C8—N1—C9 | 124.79 (15) | C11—C16—H16 | 120.0 |
C7—N1—C9 | 123.11 (15) | C15—C16—H16 | 120.0 |
C23—N2—C24 | 112.20 (15) | C22—C17—C18 | 117.44 (17) |
C23—N2—C25 | 123.49 (14) | C22—C17—H17 | 121.3 |
C24—N2—C25 | 124.31 (15) | C18—C17—H17 | 121.3 |
C2—C1—C6 | 121.15 (18) | C17—C18—C19 | 121.21 (19) |
C2—C1—C8 | 130.80 (19) | C17—C18—H18 | 119.4 |
C6—C1—C8 | 108.04 (16) | C19—C18—H18 | 119.4 |
C1—C2—C3 | 117.5 (2) | C18—C19—C20 | 121.06 (18) |
C1—C2—H2 | 121.2 | C18—C19—H19 | 119.5 |
C3—C2—H2 | 121.2 | C20—C19—H19 | 119.5 |
C4—C3—C2 | 120.9 (2) | C21—C20—C19 | 117.59 (17) |
C4—C3—H3 | 119.5 | C21—C20—H20 | 121.2 |
C2—C3—H3 | 119.5 | C19—C20—H20 | 121.2 |
C3—C4—C5 | 121.3 (2) | C20—C21—C22 | 121.16 (17) |
C3—C4—H4 | 119.3 | C20—C21—C24 | 130.92 (16) |
C5—C4—H4 | 119.3 | C22—C21—C24 | 107.92 (14) |
C6—C5—C4 | 117.6 (2) | C17—C22—C21 | 121.55 (16) |
C6—C5—H5 | 121.2 | C17—C22—C23 | 130.62 (16) |
C4—C5—H5 | 121.2 | C21—C22—C23 | 107.84 (15) |
C5—C6—C1 | 121.38 (19) | O4—C23—N2 | 124.77 (17) |
C5—C6—C7 | 130.50 (19) | O4—C23—C22 | 129.01 (17) |
C1—C6—C7 | 108.11 (16) | N2—C23—C22 | 106.22 (14) |
O1—C7—N1 | 124.46 (18) | O5—C24—N2 | 124.39 (17) |
O1—C7—C6 | 129.59 (18) | O5—C24—C21 | 129.80 (16) |
N1—C7—C6 | 105.93 (16) | N2—C24—C21 | 105.81 (14) |
O2—C8—N1 | 124.82 (18) | N2—C25—C26 | 112.05 (15) |
O2—C8—C1 | 129.32 (18) | N2—C25—H25A | 109.2 |
N1—C8—C1 | 105.86 (16) | C26—C25—H25A | 109.2 |
N1—C9—C10 | 113.02 (15) | N2—C25—H25B | 109.2 |
N1—C9—H9A | 109.0 | C26—C25—H25B | 109.2 |
C10—C9—H9A | 109.0 | H25A—C25—H25B | 107.9 |
N1—C9—H9B | 109.0 | O6—C26—C27 | 122.27 (17) |
C10—C9—H9B | 109.0 | O6—C26—C25 | 119.58 (17) |
H9A—C9—H9B | 107.8 | C27—C26—C25 | 118.14 (15) |
O3—C10—C11 | 122.05 (18) | C28—C27—C32 | 118.56 (17) |
O3—C10—C9 | 120.48 (18) | C28—C27—C26 | 122.53 (16) |
C11—C10—C9 | 117.47 (16) | C32—C27—C26 | 118.90 (16) |
C12—C11—C16 | 118.58 (19) | C29—C28—C27 | 120.46 (17) |
C12—C11—C10 | 122.66 (17) | C29—C28—H28 | 119.8 |
C16—C11—C10 | 118.74 (19) | C27—C28—H28 | 119.8 |
C13—C12—C11 | 120.6 (2) | C30—C29—C28 | 120.52 (19) |
C13—C12—H12 | 119.7 | C30—C29—H29 | 119.7 |
C11—C12—H12 | 119.7 | C28—C29—H29 | 119.7 |
C14—C13—C12 | 120.7 (2) | C29—C30—C31 | 119.8 (2) |
C14—C13—H13 | 119.6 | C29—C30—H30 | 120.1 |
C12—C13—H13 | 119.6 | C31—C30—H30 | 120.1 |
C13—C14—C15 | 119.9 (2) | C30—C31—C32 | 120.54 (19) |
C13—C14—H14 | 120.1 | C30—C31—H31 | 119.7 |
C15—C14—H14 | 120.1 | C32—C31—H31 | 119.7 |
C14—C15—C16 | 120.2 (2) | C31—C32—C27 | 120.11 (19) |
C14—C15—H15 | 119.9 | C31—C32—H32 | 119.9 |
C16—C15—H15 | 119.9 | C27—C32—H32 | 119.9 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···O1i | 0.97 | 2.59 | 3.451 (2) | 147 |
C9—H9B···O4 | 0.97 | 2.56 | 3.506 (2) | 165 |
C14—H14···O6ii | 0.93 | 2.59 | 3.206 (3) | 124 |
C15—H15···O1iii | 0.93 | 2.57 | 3.438 (3) | 155 |
C20—H20···O4iv | 0.93 | 2.54 | 3.447 (2) | 166 |
C30—H30···O3v | 0.93 | 2.57 | 3.214 (3) | 127 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z−3/2; (iii) −x+1, y+1/2, −z+1/2; (iv) x, −y+1/2, z−1/2; (v) x, −y−1/2, z−1/2. |