The title compound, C23H27ClN2O2, has been synthesized by the reaction of 9-(4-chlorophenyl)-3,3,6,6-tetramethyl-2,3,4,5,6,7-hexahydroxanthene-1,8-dione with hydrazine in ethanol under microwave irradiation. The dihydropyridine ring adopts a boat conformation.
Supporting information
CCDC reference: 294048
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.008 Å
- R factor = 0.078
- wR factor = 0.170
- Data-to-parameter ratio = 13.1
checkCIF/PLATON results
No syntax errors found
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 25.02
From the CIF: _diffrn_reflns_theta_full 25.02
From the CIF: _reflns_number_total 3622
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 3829
Completeness (_total/calc) 94.59%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.95
PLAT028_ALERT_3_C _diffrn_measured_fraction_theta_max Low ....... 0.92
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
PLAT414_ALERT_2_C Short Intra D-H..H-X H2B .. H12A .. 1.91 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2B ... ?
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 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
4 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, 1998); 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.
10-Amino-9-(4-chlorophenyl)-3,3,6,6-tetramethyl-3,4,5,6,9,10-
hexahydroacridine-1,8(2
H,7H)-dione
top
Crystal data top
C23H27ClN2O2 | F(000) = 424 |
Mr = 398.92 | Dx = 1.222 Mg m−3 |
Triclinic, P1 | Melting point = 550–551 K |
a = 8.8057 (18) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.211 (2) Å | Cell parameters from 1226 reflections |
c = 12.097 (3) Å | θ = 2.7–27.5° |
α = 70.148 (3)° | µ = 0.20 mm−1 |
β = 84.255 (4)° | T = 298 K |
γ = 74.874 (4)° | Chunk, yellow |
V = 1084.2 (4) Å3 | 0.28 × 0.21 × 0.08 mm |
Z = 2 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3322 independent reflections |
Radiation source: fine-focus sealed tube | 2330 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
φ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→7 |
Tmin = 0.947, Tmax = 0.985 | k = −13→10 |
4387 measured reflections | l = −14→14 |
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)] = 0.078 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0434P)2] where P = (Fo2 + 2Fc2)/3 |
3322 reflections | (Δ/σ)max < 0.001 |
253 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.31 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 | |
Cl1 | 0.46158 (18) | 1.07869 (14) | 0.84224 (12) | 0.0648 (5) | |
N1 | 1.0730 (4) | 0.4533 (4) | 0.7612 (3) | 0.0330 (10) | |
N2 | 1.2242 (4) | 0.3665 (4) | 0.7984 (3) | 0.0566 (14) | |
H2A | 1.3053 | 0.3751 | 0.7532 | 0.068* | |
H2B | 1.2335 | 0.3061 | 0.8658 | 0.068* | |
O1 | 0.7659 (4) | 0.7494 (4) | 0.4338 (3) | 0.0627 (12) | |
O2 | 0.5176 (4) | 0.4766 (4) | 0.7915 (3) | 0.0594 (11) | |
C1 | 1.0578 (5) | 0.5517 (5) | 0.6515 (4) | 0.0337 (12) | |
C2 | 1.2103 (6) | 0.5781 (5) | 0.5866 (4) | 0.0481 (15) | |
H2C | 1.2524 | 0.5134 | 0.5477 | 0.058* | |
H2D | 1.2869 | 0.5677 | 0.6436 | 0.058* | |
C3 | 1.1885 (6) | 0.7155 (5) | 0.4945 (4) | 0.0468 (15) | |
C4 | 1.0455 (6) | 0.7376 (5) | 0.4176 (4) | 0.0494 (15) | |
H4A | 1.0206 | 0.8281 | 0.3671 | 0.059* | |
H4B | 1.0771 | 0.6838 | 0.3672 | 0.059* | |
C5 | 0.8967 (6) | 0.7078 (5) | 0.4838 (4) | 0.0435 (14) | |
C6 | 0.9118 (5) | 0.6192 (5) | 0.6051 (4) | 0.0354 (12) | |
C7 | 0.7595 (6) | 0.6035 (5) | 0.6771 (4) | 0.0392 (13) | |
H7 | 0.6840 | 0.5988 | 0.6253 | 0.047* | |
C8 | 0.7903 (5) | 0.4756 (5) | 0.7788 (4) | 0.0350 (12) | |
C9 | 0.6521 (6) | 0.4217 (5) | 0.8326 (4) | 0.0413 (13) | |
C10 | 0.6830 (6) | 0.2923 (6) | 0.9317 (5) | 0.0584 (17) | |
H10A | 0.6983 | 0.2225 | 0.8985 | 0.070* | |
H10B | 0.5905 | 0.2896 | 0.9824 | 0.070* | |
C11 | 0.8269 (7) | 0.2661 (6) | 1.0072 (4) | 0.0527 (16) | |
C12 | 0.9709 (6) | 0.2860 (5) | 0.9242 (4) | 0.0418 (13) | |
H12A | 1.0557 | 0.2871 | 0.9689 | 0.050* | |
H12B | 1.0065 | 0.2120 | 0.8958 | 0.050* | |
C13 | 0.9382 (6) | 0.4106 (5) | 0.8193 (4) | 0.0353 (12) | |
C14 | 1.3404 (6) | 0.7225 (6) | 0.4198 (4) | 0.0639 (18) | |
H14A | 1.3283 | 0.8082 | 0.3627 | 0.096* | |
H14B | 1.3603 | 0.6587 | 0.3802 | 0.096* | |
H14C | 1.4271 | 0.7048 | 0.4699 | 0.096* | |
C15 | 1.1527 (7) | 0.8221 (6) | 0.5554 (5) | 0.0676 (18) | |
H15A | 1.1393 | 0.9069 | 0.4967 | 0.101* | |
H15B | 1.2386 | 0.8074 | 0.6052 | 0.101* | |
H15C | 1.0580 | 0.8177 | 0.6019 | 0.101* | |
C16 | 0.7901 (7) | 0.3631 (6) | 1.0778 (5) | 0.0727 (19) | |
H16A | 0.8798 | 0.3493 | 1.1236 | 0.109* | |
H16B | 0.7013 | 0.3489 | 1.1290 | 0.109* | |
H16C | 0.7664 | 0.4511 | 1.0243 | 0.109* | |
C17 | 0.8630 (7) | 0.1254 (6) | 1.0946 (5) | 0.076 (2) | |
H17A | 0.8872 | 0.0644 | 1.0520 | 0.114* | |
H17B | 0.7730 | 0.1121 | 1.1447 | 0.114* | |
H17C | 0.9514 | 0.1121 | 1.1417 | 0.114* | |
C18 | 0.6849 (5) | 0.7248 (5) | 0.7178 (4) | 0.0384 (13) | |
C19 | 0.7306 (6) | 0.7332 (5) | 0.8227 (4) | 0.0509 (15) | |
H19 | 0.8068 | 0.6647 | 0.8686 | 0.061* | |
C20 | 0.6642 (6) | 0.8428 (6) | 0.8605 (5) | 0.0545 (16) | |
H20 | 0.6973 | 0.8461 | 0.9298 | 0.065* | |
C21 | 0.5500 (6) | 0.9444 (5) | 0.7934 (4) | 0.0465 (14) | |
C22 | 0.5017 (6) | 0.9417 (5) | 0.6883 (4) | 0.0505 (15) | |
H22 | 0.4262 | 1.0110 | 0.6424 | 0.061* | |
C23 | 0.5704 (5) | 0.8306 (5) | 0.6529 (4) | 0.0441 (14) | |
H23 | 0.5374 | 0.8284 | 0.5831 | 0.053* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0863 (12) | 0.0426 (9) | 0.0595 (10) | 0.0006 (8) | −0.0014 (8) | −0.0210 (7) |
N1 | 0.017 (2) | 0.037 (2) | 0.040 (2) | 0.0023 (19) | −0.0021 (19) | −0.012 (2) |
N2 | 0.034 (3) | 0.059 (3) | 0.048 (3) | −0.005 (2) | −0.001 (2) | 0.015 (2) |
O1 | 0.041 (2) | 0.080 (3) | 0.050 (2) | 0.003 (2) | −0.0119 (19) | −0.011 (2) |
O2 | 0.031 (2) | 0.079 (3) | 0.071 (3) | −0.013 (2) | −0.003 (2) | −0.027 (2) |
C1 | 0.024 (3) | 0.042 (3) | 0.040 (3) | −0.012 (2) | 0.001 (2) | −0.016 (2) |
C2 | 0.041 (3) | 0.056 (4) | 0.051 (3) | −0.017 (3) | −0.006 (3) | −0.015 (3) |
C3 | 0.052 (4) | 0.047 (4) | 0.043 (3) | −0.016 (3) | −0.005 (3) | −0.013 (3) |
C4 | 0.052 (4) | 0.055 (4) | 0.038 (3) | −0.012 (3) | −0.001 (3) | −0.013 (3) |
C5 | 0.046 (4) | 0.039 (3) | 0.049 (3) | −0.004 (3) | −0.011 (3) | −0.019 (3) |
C6 | 0.032 (3) | 0.044 (3) | 0.033 (3) | −0.011 (3) | 0.004 (2) | −0.015 (2) |
C7 | 0.033 (3) | 0.041 (3) | 0.047 (3) | −0.005 (3) | −0.014 (3) | −0.017 (3) |
C8 | 0.026 (3) | 0.046 (3) | 0.040 (3) | −0.007 (2) | 0.003 (2) | −0.024 (2) |
C9 | 0.017 (3) | 0.062 (4) | 0.054 (3) | −0.010 (3) | 0.008 (2) | −0.032 (3) |
C10 | 0.043 (4) | 0.069 (5) | 0.064 (4) | −0.026 (3) | 0.014 (3) | −0.018 (3) |
C11 | 0.057 (4) | 0.054 (4) | 0.044 (3) | −0.018 (3) | −0.002 (3) | −0.007 (3) |
C12 | 0.040 (3) | 0.041 (3) | 0.042 (3) | −0.009 (3) | 0.002 (3) | −0.013 (2) |
C13 | 0.034 (3) | 0.040 (3) | 0.036 (3) | −0.014 (2) | 0.001 (2) | −0.014 (2) |
C14 | 0.065 (4) | 0.079 (5) | 0.051 (3) | −0.033 (4) | 0.011 (3) | −0.018 (3) |
C15 | 0.079 (5) | 0.052 (4) | 0.078 (4) | −0.020 (4) | −0.006 (3) | −0.025 (3) |
C16 | 0.078 (5) | 0.088 (5) | 0.055 (4) | −0.010 (4) | 0.004 (3) | −0.035 (3) |
C17 | 0.068 (5) | 0.072 (5) | 0.068 (4) | −0.019 (4) | 0.013 (3) | 0.000 (4) |
C18 | 0.025 (3) | 0.049 (3) | 0.039 (3) | −0.003 (2) | −0.002 (2) | −0.015 (3) |
C19 | 0.036 (3) | 0.056 (4) | 0.057 (3) | 0.008 (3) | −0.013 (3) | −0.026 (3) |
C20 | 0.055 (4) | 0.056 (4) | 0.056 (4) | −0.006 (3) | −0.015 (3) | −0.024 (3) |
C21 | 0.055 (4) | 0.036 (3) | 0.046 (3) | −0.003 (3) | 0.002 (3) | −0.017 (3) |
C22 | 0.050 (4) | 0.045 (4) | 0.042 (3) | 0.010 (3) | −0.010 (3) | −0.009 (3) |
C23 | 0.038 (3) | 0.050 (4) | 0.041 (3) | 0.006 (3) | −0.004 (3) | −0.021 (3) |
Geometric parameters (Å, º) top
Cl1—C21 | 1.767 (6) | C10—H10B | 0.970 |
N1—C1 | 1.399 (5) | C11—C17 | 1.543 (7) |
N1—C13 | 1.426 (5) | C11—C16 | 1.551 (8) |
N1—N2 | 1.438 (5) | C11—C12 | 1.552 (7) |
N2—H2A | 0.860 | C12—C13 | 1.518 (6) |
N2—H2B | 0.860 | C12—H12A | 0.970 |
O1—C5 | 1.256 (5) | C12—H12B | 0.970 |
O2—C9 | 1.248 (5) | C14—H14A | 0.960 |
C1—C6 | 1.375 (6) | C14—H14B | 0.960 |
C1—C2 | 1.532 (6) | C14—H14C | 0.960 |
C2—C3 | 1.541 (6) | C15—H15A | 0.960 |
C2—H2C | 0.970 | C15—H15B | 0.960 |
C2—H2D | 0.970 | C15—H15C | 0.960 |
C3—C14 | 1.542 (7) | C16—H16A | 0.960 |
C3—C15 | 1.557 (8) | C16—H16B | 0.960 |
C3—C4 | 1.558 (6) | C16—H16C | 0.960 |
C4—C5 | 1.519 (6) | C17—H17A | 0.960 |
C4—H4A | 0.970 | C17—H17B | 0.960 |
C4—H4B | 0.970 | C17—H17C | 0.960 |
C5—C6 | 1.462 (6) | C18—C23 | 1.393 (6) |
C6—C7 | 1.540 (6) | C18—C19 | 1.409 (6) |
C7—C8 | 1.520 (6) | C19—C20 | 1.419 (8) |
C7—C18 | 1.564 (7) | C19—H19 | 0.930 |
C7—H7 | 0.980 | C20—C21 | 1.381 (7) |
C8—C13 | 1.362 (6) | C20—H20 | 0.930 |
C8—C9 | 1.492 (6) | C21—C22 | 1.393 (6) |
C9—C10 | 1.514 (7) | C22—C23 | 1.420 (7) |
C10—C11 | 1.543 (6) | C22—H22 | 0.930 |
C10—H10A | 0.970 | C23—H23 | 0.930 |
| | | |
C1—N1—C13 | 120.0 (3) | C10—C11—C12 | 108.4 (4) |
C1—N1—N2 | 120.0 (4) | C17—C11—C12 | 109.3 (5) |
C13—N1—N2 | 116.9 (4) | C16—C11—C12 | 110.7 (4) |
N1—N2—H2A | 120.0 | C13—C12—C11 | 114.1 (4) |
N1—N2—H2B | 120.0 | C13—C12—H12A | 108.7 |
H2A—N2—H2B | 120.0 | C11—C12—H12A | 108.7 |
C6—C1—N1 | 120.7 (4) | C13—C12—H12B | 108.7 |
C6—C1—C2 | 122.4 (4) | C11—C12—H12B | 108.7 |
N1—C1—C2 | 116.9 (4) | H12A—C12—H12B | 107.6 |
C1—C2—C3 | 113.5 (5) | C8—C13—N1 | 121.4 (4) |
C1—C2—H2C | 108.9 | C8—C13—C12 | 122.7 (4) |
C3—C2—H2C | 108.9 | N1—C13—C12 | 115.9 (4) |
C1—C2—H2D | 108.9 | C3—C14—H14A | 109.5 |
C3—C2—H2D | 108.9 | C3—C14—H14B | 109.5 |
H2C—C2—H2D | 107.7 | H14A—C14—H14B | 109.5 |
C2—C3—C14 | 108.9 (5) | C3—C14—H14C | 109.5 |
C2—C3—C15 | 110.7 (4) | H14A—C14—H14C | 109.5 |
C14—C3—C15 | 109.6 (4) | H14B—C14—H14C | 109.5 |
C2—C3—C4 | 107.4 (4) | C3—C15—H15A | 109.5 |
C14—C3—C4 | 111.3 (4) | C3—C15—H15B | 109.5 |
C15—C3—C4 | 108.9 (5) | H15A—C15—H15B | 109.5 |
C5—C4—C3 | 116.1 (4) | C3—C15—H15C | 109.5 |
C5—C4—H4A | 108.3 | H15A—C15—H15C | 109.5 |
C3—C4—H4A | 108.3 | H15B—C15—H15C | 109.5 |
C5—C4—H4B | 108.3 | C11—C16—H16A | 109.5 |
C3—C4—H4B | 108.3 | C11—C16—H16B | 109.5 |
H4A—C4—H4B | 107.4 | H16A—C16—H16B | 109.5 |
O1—C5—C6 | 120.4 (5) | C11—C16—H16C | 109.5 |
O1—C5—C4 | 121.4 (4) | H16A—C16—H16C | 109.5 |
C6—C5—C4 | 118.0 (4) | H16B—C16—H16C | 109.5 |
C1—C6—C5 | 120.4 (5) | C11—C17—H17A | 109.5 |
C1—C6—C7 | 121.9 (4) | C11—C17—H17B | 109.5 |
C5—C6—C7 | 117.7 (4) | H17A—C17—H17B | 109.5 |
C8—C7—C6 | 110.2 (4) | C11—C17—H17C | 109.5 |
C8—C7—C18 | 112.7 (4) | H17A—C17—H17C | 109.5 |
C6—C7—C18 | 111.3 (4) | H17B—C17—H17C | 109.5 |
C8—C7—H7 | 107.5 | C23—C18—C19 | 116.1 (5) |
C6—C7—H7 | 107.5 | C23—C18—C7 | 122.3 (4) |
C18—C7—H7 | 107.5 | C19—C18—C7 | 121.6 (4) |
C13—C8—C9 | 120.7 (4) | C18—C19—C20 | 122.2 (5) |
C13—C8—C7 | 121.8 (4) | C18—C19—H19 | 118.9 |
C9—C8—C7 | 117.5 (4) | C20—C19—H19 | 118.9 |
O2—C9—C8 | 121.0 (5) | C21—C20—C19 | 119.3 (5) |
O2—C9—C10 | 121.2 (4) | C21—C20—H20 | 120.3 |
C8—C9—C10 | 117.6 (4) | C19—C20—H20 | 120.3 |
C9—C10—C11 | 114.6 (4) | C20—C21—C22 | 120.8 (5) |
C9—C10—H10A | 108.6 | C20—C21—Cl1 | 119.7 (4) |
C11—C10—H10A | 108.6 | C22—C21—Cl1 | 119.4 (4) |
C9—C10—H10B | 108.6 | C21—C22—C23 | 118.4 (4) |
C11—C10—H10B | 108.6 | C21—C22—H22 | 120.8 |
H10A—C10—H10B | 107.6 | C23—C22—H22 | 120.8 |
C10—C11—C17 | 111.0 (4) | C18—C23—C22 | 123.1 (4) |
C10—C11—C16 | 108.6 (5) | C18—C23—H23 | 118.4 |
C17—C11—C16 | 108.7 (4) | C22—C23—H23 | 118.4 |
| | | |
C13—N1—C1—C6 | 8.0 (7) | C7—C8—C9—C10 | 178.3 (5) |
N2—N1—C1—C6 | 167.8 (4) | O2—C9—C10—C11 | −154.8 (5) |
C13—N1—C1—C2 | −171.2 (4) | C8—C9—C10—C11 | 30.3 (7) |
N2—N1—C1—C2 | −11.5 (6) | C9—C10—C11—C17 | −172.2 (5) |
C6—C1—C2—C3 | 22.9 (7) | C9—C10—C11—C16 | 68.3 (6) |
N1—C1—C2—C3 | −157.8 (4) | C9—C10—C11—C12 | −52.1 (7) |
C1—C2—C3—C14 | −169.8 (4) | C10—C11—C12—C13 | 47.1 (6) |
C1—C2—C3—C15 | 69.7 (5) | C17—C11—C12—C13 | 168.3 (4) |
C1—C2—C3—C4 | −49.1 (6) | C16—C11—C12—C13 | −72.0 (5) |
C2—C3—C4—C5 | 49.7 (6) | C9—C8—C13—N1 | 173.3 (4) |
C14—C3—C4—C5 | 168.8 (4) | C7—C8—C13—N1 | −5.8 (8) |
C15—C3—C4—C5 | −70.3 (6) | C9—C8—C13—C12 | −3.7 (8) |
C3—C4—C5—O1 | 163.3 (5) | C7—C8—C13—C12 | 177.2 (4) |
C3—C4—C5—C6 | −22.0 (7) | C1—N1—C13—C8 | −9.4 (7) |
N1—C1—C6—C5 | −170.9 (4) | N2—N1—C13—C8 | −169.8 (4) |
C2—C1—C6—C5 | 8.3 (7) | C1—N1—C13—C12 | 167.8 (4) |
N1—C1—C6—C7 | 8.2 (7) | N2—N1—C13—C12 | 7.4 (6) |
C2—C1—C6—C7 | −172.6 (4) | C11—C12—C13—C8 | −21.1 (7) |
O1—C5—C6—C1 | 165.9 (5) | C11—C12—C13—N1 | 161.8 (4) |
C4—C5—C6—C1 | −8.7 (7) | C8—C7—C18—C23 | −142.5 (4) |
O1—C5—C6—C7 | −13.3 (7) | C6—C7—C18—C23 | 93.1 (5) |
C4—C5—C6—C7 | 172.1 (4) | C8—C7—C18—C19 | 37.7 (6) |
C1—C6—C7—C8 | −20.8 (6) | C6—C7—C18—C19 | −86.7 (5) |
C5—C6—C7—C8 | 158.4 (4) | C23—C18—C19—C20 | 0.0 (7) |
C1—C6—C7—C18 | 105.0 (5) | C7—C18—C19—C20 | 179.9 (5) |
C5—C6—C7—C18 | −75.8 (5) | C18—C19—C20—C21 | 0.6 (8) |
C6—C7—C8—C13 | 19.5 (6) | C19—C20—C21—C22 | −1.2 (8) |
C18—C7—C8—C13 | −105.5 (6) | C19—C20—C21—Cl1 | 177.8 (4) |
C6—C7—C8—C9 | −159.6 (4) | C20—C21—C22—C23 | 1.3 (8) |
C18—C7—C8—C9 | 75.4 (5) | Cl1—C21—C22—C23 | −177.8 (4) |
C13—C8—C9—O2 | −175.7 (5) | C19—C18—C23—C22 | 0.0 (7) |
C7—C8—C9—O2 | 3.4 (7) | C7—C18—C23—C22 | −179.8 (5) |
C13—C8—C9—C10 | −0.8 (7) | C21—C22—C23—C18 | −0.6 (8) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2i | 0.86 | 2.58 | 3.123 (5) | 122 |
Symmetry code: (i) x+1, y, z. |