The title compound, C23H25Cl2NO2, was synthesized by the reaction of 5,5-dimethylcyclohexane-1,3-dione with 3,4-dichlorobenzaldehyde and ammonium acetate under solvent-free conditions at 353 K. X-ray analysis reveals that the dihydropyridine and cyclohexene rings adopt envelope conformations.
Supporting information
CCDC reference: 605017
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.009 Å
- R factor = 0.069
- wR factor = 0.186
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.20
PLAT230_ALERT_2_C Hirshfeld Test Diff for C20 - C21 .. 5.99 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C22
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C20
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl2 .. O2 .. 3.13 Ang.
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 25.00
From the CIF: _reflns_number_total 3745
Count of symmetry unique reflns 2021
Completeness (_total/calc) 185.30%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1724
Fraction of Friedel pairs measured 0.853
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 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, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
9-(3,4-Dichlorophenyl)-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-
decahydroacridine-1,8-dione
top
Crystal data top
C23H25Cl2NO2 | Dx = 1.278 Mg m−3 |
Mr = 418.34 | Melting point: 573 K |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 1556 reflections |
a = 14.155 (3) Å | θ = 2.4–18.8° |
b = 14.352 (3) Å | µ = 0.32 mm−1 |
c = 10.704 (3) Å | T = 298 K |
V = 2174.6 (9) Å3 | Block, colourless |
Z = 4 | 0.43 × 0.40 × 0.38 mm |
F(000) = 880 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3745 independent reflections |
Radiation source: fine-focus sealed tube | 1776 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.081 |
φ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→16 |
Tmin = 0.876, Tmax = 0.889 | k = −17→14 |
10745 measured reflections | l = −12→12 |
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)] = 0.069 | H-atom parameters constrained |
wR(F2) = 0.186 | w = 1/[σ2(Fo2) + (0.0795P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
3745 reflections | Δρmax = 0.74 e Å−3 |
253 parameters | Δρmin = −0.34 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1745 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.09 (14) |
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 | |
Cl1 | 0.60043 (17) | 0.71529 (19) | −0.3314 (3) | 0.1198 (10) | |
Cl2 | 0.71783 (17) | 0.88098 (16) | −0.4403 (2) | 0.1019 (8) | |
N1 | 1.0556 (3) | 0.6949 (3) | 0.0807 (5) | 0.0513 (14) | |
H1 | 1.1117 | 0.7129 | 0.1003 | 0.062* | |
O1 | 0.7301 (3) | 0.7382 (3) | 0.1328 (4) | 0.0638 (12) | |
O2 | 0.8733 (3) | 0.4889 (3) | −0.1644 (4) | 0.0673 (13) | |
C1 | 0.9795 (4) | 0.7415 (4) | 0.1290 (5) | 0.0403 (14) | |
C2 | 1.0029 (4) | 0.8109 (4) | 0.2277 (6) | 0.0487 (15) | |
H2A | 1.0622 | 0.8410 | 0.2066 | 0.058* | |
H2B | 1.0116 | 0.7786 | 0.3065 | 0.058* | |
C3 | 0.9258 (5) | 0.8859 (4) | 0.2436 (6) | 0.0576 (18) | |
C4 | 0.8315 (5) | 0.8318 (5) | 0.2552 (7) | 0.0612 (19) | |
H4A | 0.8304 | 0.8009 | 0.3357 | 0.073* | |
H4B | 0.7801 | 0.8766 | 0.2544 | 0.073* | |
C5 | 0.8131 (5) | 0.7617 (4) | 0.1578 (6) | 0.0497 (16) | |
C6 | 0.8902 (4) | 0.7189 (4) | 0.0951 (6) | 0.0407 (15) | |
C7 | 0.8705 (4) | 0.6512 (4) | −0.0107 (6) | 0.0441 (15) | |
H7 | 0.8220 | 0.6072 | 0.0172 | 0.053* | |
C8 | 0.9590 (4) | 0.5964 (4) | −0.0443 (5) | 0.0419 (15) | |
C9 | 0.9519 (4) | 0.5168 (4) | −0.1291 (6) | 0.0493 (16) | |
C10 | 1.0414 (5) | 0.4727 (5) | −0.1737 (7) | 0.0627 (19) | |
H10A | 1.0636 | 0.5060 | −0.2469 | 0.075* | |
H10B | 1.0283 | 0.4090 | −0.1985 | 0.075* | |
C11 | 1.1188 (4) | 0.4723 (4) | −0.0763 (6) | 0.0563 (17) | |
C12 | 1.1351 (4) | 0.5711 (4) | −0.0282 (7) | 0.0598 (18) | |
H12A | 1.1739 | 0.5685 | 0.0464 | 0.072* | |
H12B | 1.1692 | 0.6065 | −0.0908 | 0.072* | |
C13 | 1.0448 (4) | 0.6202 (4) | 0.0017 (5) | 0.0405 (14) | |
C14 | 0.9472 (5) | 0.9404 (5) | 0.3585 (7) | 0.079 (2) | |
H14A | 0.9506 | 0.8990 | 0.4288 | 0.119* | |
H14B | 0.8981 | 0.9854 | 0.3723 | 0.119* | |
H14C | 1.0065 | 0.9718 | 0.3485 | 0.119* | |
C15 | 0.9193 (6) | 0.9502 (4) | 0.1317 (7) | 0.080 (2) | |
H15A | 0.9056 | 0.9143 | 0.0583 | 0.120* | |
H15B | 0.9784 | 0.9821 | 0.1209 | 0.120* | |
H15C | 0.8699 | 0.9949 | 0.1451 | 0.120* | |
C16 | 1.0937 (5) | 0.4082 (5) | 0.0330 (6) | 0.072 (2) | |
H16A | 1.0839 | 0.3460 | 0.0025 | 0.108* | |
H16B | 1.0371 | 0.4301 | 0.0725 | 0.108* | |
H16C | 1.1445 | 0.4081 | 0.0924 | 0.108* | |
C17 | 1.2127 (5) | 0.4374 (5) | −0.1317 (8) | 0.083 (2) | |
H17A | 1.2048 | 0.3750 | −0.1621 | 0.125* | |
H17B | 1.2606 | 0.4382 | −0.0682 | 0.125* | |
H17C | 1.2313 | 0.4773 | −0.1993 | 0.125* | |
C18 | 0.8317 (4) | 0.7053 (4) | −0.1238 (6) | 0.0503 (15) | |
C19 | 0.7440 (5) | 0.6862 (5) | −0.1745 (7) | 0.0612 (18) | |
H19 | 0.7074 | 0.6384 | −0.1413 | 0.073* | |
C20 | 0.7097 (5) | 0.7385 (6) | −0.2758 (7) | 0.067 (2) | |
C21 | 0.7627 (6) | 0.8109 (6) | −0.3217 (7) | 0.069 (2) | |
C22 | 0.8464 (7) | 0.8287 (7) | −0.2733 (8) | 0.092 (3) | |
H22 | 0.8824 | 0.8771 | −0.3060 | 0.110* | |
C23 | 0.8822 (6) | 0.7759 (5) | −0.1729 (6) | 0.068 (2) | |
H23 | 0.9414 | 0.7900 | −0.1403 | 0.082* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0849 (16) | 0.140 (2) | 0.135 (2) | −0.0151 (15) | −0.0468 (16) | 0.0300 (18) |
Cl2 | 0.1141 (16) | 0.1256 (17) | 0.0658 (12) | 0.0388 (14) | −0.0009 (13) | 0.0238 (13) |
N1 | 0.038 (3) | 0.041 (3) | 0.075 (4) | 0.002 (2) | 0.009 (3) | −0.018 (3) |
O1 | 0.038 (3) | 0.078 (3) | 0.075 (3) | 0.009 (2) | −0.004 (2) | 0.002 (3) |
O2 | 0.057 (3) | 0.071 (3) | 0.074 (3) | −0.017 (2) | −0.015 (2) | −0.011 (3) |
C1 | 0.037 (4) | 0.038 (3) | 0.046 (3) | −0.002 (3) | 0.006 (3) | −0.002 (3) |
C2 | 0.046 (4) | 0.049 (3) | 0.051 (4) | 0.004 (3) | 0.004 (3) | −0.013 (3) |
C3 | 0.068 (5) | 0.048 (4) | 0.057 (4) | 0.006 (3) | 0.003 (4) | −0.011 (4) |
C4 | 0.059 (5) | 0.066 (4) | 0.059 (5) | 0.020 (4) | 0.013 (4) | 0.005 (4) |
C5 | 0.046 (4) | 0.043 (4) | 0.060 (4) | 0.005 (3) | −0.004 (3) | 0.014 (3) |
C6 | 0.027 (3) | 0.039 (3) | 0.057 (4) | 0.003 (3) | 0.003 (3) | 0.003 (3) |
C7 | 0.038 (4) | 0.042 (3) | 0.053 (4) | −0.008 (3) | −0.003 (3) | 0.000 (3) |
C8 | 0.045 (4) | 0.031 (3) | 0.049 (4) | −0.001 (3) | −0.005 (3) | 0.000 (3) |
C9 | 0.052 (4) | 0.051 (4) | 0.045 (4) | −0.001 (3) | 0.000 (3) | 0.005 (3) |
C10 | 0.075 (5) | 0.055 (4) | 0.058 (4) | −0.004 (4) | 0.000 (4) | −0.019 (4) |
C11 | 0.067 (4) | 0.045 (4) | 0.058 (4) | 0.006 (3) | −0.001 (4) | −0.010 (3) |
C12 | 0.055 (4) | 0.044 (4) | 0.081 (5) | 0.010 (3) | 0.008 (4) | −0.013 (4) |
C13 | 0.031 (3) | 0.036 (3) | 0.055 (4) | −0.004 (3) | 0.008 (3) | −0.013 (3) |
C14 | 0.097 (6) | 0.070 (5) | 0.071 (5) | 0.014 (4) | 0.020 (5) | −0.021 (4) |
C15 | 0.113 (6) | 0.046 (4) | 0.082 (5) | 0.000 (4) | 0.007 (5) | −0.001 (4) |
C16 | 0.082 (5) | 0.068 (5) | 0.067 (5) | 0.015 (4) | 0.003 (4) | 0.012 (4) |
C17 | 0.061 (5) | 0.096 (6) | 0.093 (6) | 0.021 (4) | 0.019 (4) | −0.036 (5) |
C18 | 0.041 (4) | 0.060 (4) | 0.050 (4) | 0.002 (3) | −0.008 (3) | −0.008 (3) |
C19 | 0.058 (5) | 0.055 (4) | 0.071 (5) | 0.013 (3) | −0.015 (4) | −0.012 (4) |
C20 | 0.045 (4) | 0.093 (5) | 0.064 (5) | 0.025 (4) | −0.023 (4) | −0.029 (5) |
C21 | 0.061 (5) | 0.091 (5) | 0.055 (5) | 0.012 (4) | 0.010 (4) | 0.007 (4) |
C22 | 0.088 (7) | 0.115 (7) | 0.072 (6) | 0.014 (5) | 0.014 (5) | 0.042 (5) |
C23 | 0.068 (5) | 0.080 (5) | 0.056 (4) | 0.000 (4) | −0.010 (4) | 0.018 (4) |
Geometric parameters (Å, º) top
Cl1—C20 | 1.690 (7) | C10—H10B | 0.97 |
Cl2—C21 | 1.739 (8) | C11—C12 | 1.526 (9) |
N1—C1 | 1.370 (7) | C11—C16 | 1.530 (9) |
N1—C13 | 1.374 (7) | C11—C17 | 1.540 (9) |
N1—H1 | 0.86 | C12—C13 | 1.494 (8) |
O1—C5 | 1.252 (7) | C12—H12A | 0.97 |
O2—C9 | 1.242 (7) | C12—H12B | 0.97 |
C1—C6 | 1.354 (8) | C14—H14A | 0.96 |
C1—C2 | 1.489 (8) | C14—H14B | 0.96 |
C2—C3 | 1.544 (8) | C14—H14C | 0.96 |
C2—H2A | 0.97 | C15—H15A | 0.96 |
C2—H2B | 0.97 | C15—H15B | 0.96 |
C3—C14 | 1.488 (9) | C15—H15C | 0.96 |
C3—C15 | 1.514 (9) | C16—H16A | 0.96 |
C3—C4 | 1.549 (9) | C16—H16B | 0.96 |
C4—C5 | 1.472 (9) | C16—H16C | 0.96 |
C4—H4A | 0.97 | C17—H17A | 0.96 |
C4—H4B | 0.97 | C17—H17B | 0.96 |
C5—C6 | 1.421 (8) | C17—H17C | 0.96 |
C6—C7 | 1.517 (8) | C18—C23 | 1.347 (9) |
C7—C8 | 1.522 (8) | C18—C19 | 1.382 (9) |
C7—C18 | 1.540 (9) | C19—C20 | 1.406 (10) |
C7—H7 | 0.98 | C19—H19 | 0.93 |
C8—C13 | 1.354 (7) | C20—C21 | 1.372 (10) |
C8—C9 | 1.463 (8) | C21—C22 | 1.318 (11) |
C9—C10 | 1.494 (8) | C22—C23 | 1.409 (10) |
C10—C11 | 1.512 (9) | C22—H22 | 0.93 |
C10—H10A | 0.97 | C23—H23 | 0.93 |
| | | |
C1—N1—C13 | 121.7 (5) | C16—C11—C17 | 107.4 (6) |
C1—N1—H1 | 119.2 | C13—C12—C11 | 112.4 (5) |
C13—N1—H1 | 119.2 | C13—C12—H12A | 109.1 |
C6—C1—N1 | 121.1 (5) | C11—C12—H12A | 109.1 |
C6—C1—C2 | 123.9 (5) | C13—C12—H12B | 109.1 |
N1—C1—C2 | 114.8 (5) | C11—C12—H12B | 109.1 |
C1—C2—C3 | 112.8 (5) | H12A—C12—H12B | 107.9 |
C1—C2—H2A | 109.0 | C8—C13—N1 | 121.4 (5) |
C3—C2—H2A | 109.0 | C8—C13—C12 | 124.8 (5) |
C1—C2—H2B | 109.0 | N1—C13—C12 | 113.8 (5) |
C3—C2—H2B | 109.0 | C3—C14—H14A | 109.5 |
H2A—C2—H2B | 107.8 | C3—C14—H14B | 109.5 |
C14—C3—C15 | 110.2 (5) | H14A—C14—H14B | 109.5 |
C14—C3—C2 | 108.3 (6) | C3—C14—H14C | 109.5 |
C15—C3—C2 | 112.4 (6) | H14A—C14—H14C | 109.5 |
C14—C3—C4 | 111.9 (6) | H14B—C14—H14C | 109.5 |
C15—C3—C4 | 108.4 (6) | C3—C15—H15A | 109.5 |
C2—C3—C4 | 105.6 (5) | C3—C15—H15B | 109.5 |
C5—C4—C3 | 116.0 (5) | H15A—C15—H15B | 109.5 |
C5—C4—H4A | 108.3 | C3—C15—H15C | 109.5 |
C3—C4—H4A | 108.3 | H15A—C15—H15C | 109.5 |
C5—C4—H4B | 108.3 | H15B—C15—H15C | 109.5 |
C3—C4—H4B | 108.3 | C11—C16—H16A | 109.5 |
H4A—C4—H4B | 107.4 | C11—C16—H16B | 109.5 |
O1—C5—C6 | 120.2 (6) | H16A—C16—H16B | 109.5 |
O1—C5—C4 | 120.1 (6) | C11—C16—H16C | 109.5 |
C6—C5—C4 | 119.7 (6) | H16A—C16—H16C | 109.5 |
C1—C6—C5 | 119.1 (6) | H16B—C16—H16C | 109.5 |
C1—C6—C7 | 121.6 (5) | C11—C17—H17A | 109.5 |
C5—C6—C7 | 119.3 (5) | C11—C17—H17B | 109.5 |
C6—C7—C8 | 110.9 (5) | H17A—C17—H17B | 109.5 |
C6—C7—C18 | 109.2 (4) | C11—C17—H17C | 109.5 |
C8—C7—C18 | 111.6 (5) | H17A—C17—H17C | 109.5 |
C6—C7—H7 | 108.3 | H17B—C17—H17C | 109.5 |
C8—C7—H7 | 108.3 | C23—C18—C19 | 118.3 (6) |
C18—C7—H7 | 108.3 | C23—C18—C7 | 119.7 (6) |
C13—C8—C9 | 119.0 (5) | C19—C18—C7 | 121.9 (6) |
C13—C8—C7 | 121.4 (5) | C18—C19—C20 | 120.4 (7) |
C9—C8—C7 | 119.6 (5) | C18—C19—H19 | 119.8 |
O2—C9—C8 | 120.1 (6) | C20—C19—H19 | 119.8 |
O2—C9—C10 | 121.8 (6) | C21—C20—C19 | 119.5 (6) |
C8—C9—C10 | 118.0 (5) | C21—C20—Cl1 | 121.5 (6) |
C9—C10—C11 | 113.3 (6) | C19—C20—Cl1 | 118.8 (7) |
C9—C10—H10A | 108.9 | C22—C21—C20 | 119.8 (7) |
C11—C10—H10A | 108.9 | C22—C21—Cl2 | 120.1 (7) |
C9—C10—H10B | 108.9 | C20—C21—Cl2 | 120.0 (6) |
C11—C10—H10B | 108.9 | C21—C22—C23 | 121.3 (8) |
H10A—C10—H10B | 107.7 | C21—C22—H22 | 119.4 |
C10—C11—C12 | 109.8 (5) | C23—C22—H22 | 119.4 |
C10—C11—C16 | 111.2 (6) | C18—C23—C22 | 120.7 (8) |
C12—C11—C16 | 109.6 (6) | C18—C23—H23 | 119.7 |
C10—C11—C17 | 111.2 (6) | C22—C23—H23 | 119.7 |
C12—C11—C17 | 107.6 (5) | | |
| | | |
C13—N1—C1—C6 | −3.7 (9) | C8—C9—C10—C11 | 35.4 (8) |
C13—N1—C1—C2 | 171.0 (5) | C9—C10—C11—C12 | −54.1 (7) |
C6—C1—C2—C3 | −27.3 (8) | C9—C10—C11—C16 | 67.4 (7) |
N1—C1—C2—C3 | 158.2 (5) | C9—C10—C11—C17 | −173.0 (5) |
C1—C2—C3—C14 | 169.7 (5) | C10—C11—C12—C13 | 46.1 (8) |
C1—C2—C3—C15 | −68.4 (7) | C16—C11—C12—C13 | −76.3 (7) |
C1—C2—C3—C4 | 49.7 (7) | C17—C11—C12—C13 | 167.2 (6) |
C14—C3—C4—C5 | −168.3 (6) | C9—C8—C13—N1 | 179.3 (5) |
C15—C3—C4—C5 | 69.9 (7) | C7—C8—C13—N1 | 0.0 (8) |
C2—C3—C4—C5 | −50.7 (7) | C9—C8—C13—C12 | 0.3 (9) |
C3—C4—C5—O1 | −155.5 (6) | C7—C8—C13—C12 | −179.0 (6) |
C3—C4—C5—C6 | 26.4 (8) | C1—N1—C13—C8 | 8.3 (8) |
N1—C1—C6—C5 | 172.9 (5) | C1—N1—C13—C12 | −172.6 (6) |
C2—C1—C6—C5 | −1.3 (9) | C11—C12—C13—C8 | −20.8 (9) |
N1—C1—C6—C7 | −8.9 (8) | C11—C12—C13—N1 | 160.2 (5) |
C2—C1—C6—C7 | 176.9 (5) | C6—C7—C18—C23 | 56.6 (7) |
O1—C5—C6—C1 | −176.1 (6) | C8—C7—C18—C23 | −66.4 (7) |
C4—C5—C6—C1 | 2.0 (8) | C6—C7—C18—C19 | −120.8 (6) |
O1—C5—C6—C7 | 5.7 (8) | C8—C7—C18—C19 | 116.2 (6) |
C4—C5—C6—C7 | −176.2 (5) | C23—C18—C19—C20 | 1.0 (9) |
C1—C6—C7—C8 | 15.3 (7) | C7—C18—C19—C20 | 178.4 (6) |
C5—C6—C7—C8 | −166.6 (5) | C18—C19—C20—C21 | −2.1 (10) |
C1—C6—C7—C18 | −108.1 (6) | C18—C19—C20—Cl1 | −177.8 (5) |
C5—C6—C7—C18 | 70.0 (6) | C19—C20—C21—C22 | 2.3 (11) |
C6—C7—C8—C13 | −10.9 (7) | Cl1—C20—C21—C22 | 177.8 (6) |
C18—C7—C8—C13 | 111.2 (6) | C19—C20—C21—Cl2 | −175.8 (5) |
C6—C7—C8—C9 | 169.8 (5) | Cl1—C20—C21—Cl2 | −0.3 (9) |
C18—C7—C8—C9 | −68.1 (6) | C20—C21—C22—C23 | −1.3 (13) |
C13—C8—C9—O2 | 174.1 (6) | Cl2—C21—C22—C23 | 176.7 (6) |
C7—C8—C9—O2 | −6.6 (8) | C19—C18—C23—C22 | 0.0 (10) |
C13—C8—C9—C10 | −7.5 (8) | C7—C18—C23—C22 | −177.5 (7) |
C7—C8—C9—C10 | 171.8 (6) | C21—C22—C23—C18 | 0.1 (12) |
O2—C9—C10—C11 | −146.3 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 1.85 | 2.708 (6) | 174 |
Symmetry code: (i) x+1/2, −y+3/2, z. |