In the title compound, C
23H
31NO
3, a modified synthetic
D-homo steroid derivative, the cyclohexene ring adjacent to the aromatic ring adopts a half-chair conformation, while the cyclohexane ring has an ideal chair conformation. The heterocyclic ring adopts a 14α-sofa conformation. The butyl substituent is nearly planar, this plane lying almost perpendicular to the least-squares plane of the heterocyclic ring. The structure displays some weak intermolecular C—H
O interactions.
Supporting information
CCDC reference: 285511
Key indicators
- Single-crystal X-ray study
- T = 160 K
- Mean (C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.109
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
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 30.03
From the CIF: _reflns_number_total 3343
Count of symmetry unique reflns 3352
Completeness (_total/calc) 99.73%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
0 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
0 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1999); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
17-Butyl-3-methoxy-17-aza-D-homoestra-1,3,5(10)-triene-16,17
a-dione
top
Crystal data top
C23H31NO3 | F(000) = 800 |
Mr = 369.49 | Dx = 1.235 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3360 reflections |
a = 5.9243 (1) Å | θ = 2.0–30.0° |
b = 11.0968 (3) Å | µ = 0.08 mm−1 |
c = 30.2328 (7) Å | T = 160 K |
V = 1987.53 (8) Å3 | Prism, colourless |
Z = 4 | 0.30 × 0.18 × 0.18 mm |
Data collection top
Nonius KappaCCD area-detector diffractometer | 2699 reflections with I > 2σ(I) |
Radiation source: Nonius FR590 sealed tube generator | Rint = 0.059 |
Horizontally mounted graphite crystal monochromator | θmax = 30.0°, θmin = 2.7° |
Detector resolution: 9 pixels mm-1 | h = −8→8 |
φ and ω scans with κ offsets | k = −15→15 |
34883 measured reflections | l = −42→42 |
3343 independent reflections | |
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)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.0577P)2 + 0.1792P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
3339 reflections | Δρmax = 0.21 e Å−3 |
247 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Absolute structure: Flack & Bernardinelli (2000) |
Primary atom site location: structure-invariant direct methods | |
Special details top
Experimental. Solvent used: n-Hexane Cooling Device: Oxford Cryosystems Cryostream 700 Crystal
mount: glued on a glass fibre Mosaicity (°.): 0.441 (1) Frames collected: 893
Seconds exposure per frame: 31 Degrees rotation per frame: 0.9
Crystal-Detector distance (mm): 46.0 |
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 | |
O16 | 0.3938 (3) | 0.06338 (12) | 0.17981 (4) | 0.0418 (4) | |
O17A | −0.2008 (2) | 0.29479 (14) | 0.22033 (4) | 0.0393 (3) | |
O31 | 0.1749 (2) | 0.03477 (13) | 0.55058 (4) | 0.0398 (3) | |
N17 | 0.0836 (3) | 0.16860 (14) | 0.20074 (4) | 0.0289 (3) | |
C1 | −0.0499 (3) | 0.17622 (17) | 0.44974 (5) | 0.0290 (4) | |
H1 | −0.1706 | 0.2268 | 0.4406 | 0.035* | |
C2 | −0.0327 (3) | 0.14596 (17) | 0.49430 (5) | 0.0309 (4) | |
H2 | −0.1402 | 0.1745 | 0.5151 | 0.037* | |
C3 | 0.1445 (3) | 0.07343 (16) | 0.50751 (5) | 0.0313 (4) | |
C4 | 0.3031 (3) | 0.03514 (17) | 0.47697 (5) | 0.0317 (4) | |
H4 | 0.4276 | −0.0119 | 0.4866 | 0.038* | |
C5 | 0.2834 (3) | 0.06427 (15) | 0.43233 (5) | 0.0272 (4) | |
C6 | 0.4565 (3) | 0.01755 (19) | 0.39995 (5) | 0.0335 (4) | |
H61 | 0.5040 | −0.0642 | 0.4092 | 0.040* | |
H62 | 0.5911 | 0.0703 | 0.4010 | 0.040* | |
C7 | 0.3702 (3) | 0.01175 (16) | 0.35230 (5) | 0.0290 (4) | |
H71 | 0.4977 | −0.0055 | 0.3321 | 0.035* | |
H72 | 0.2592 | −0.0545 | 0.3495 | 0.035* | |
C8 | 0.2597 (3) | 0.13068 (15) | 0.33920 (5) | 0.0237 (3) | |
H8 | 0.3728 | 0.1967 | 0.3432 | 0.028* | |
C9 | 0.0567 (3) | 0.15701 (16) | 0.36911 (5) | 0.0254 (4) | |
H9 | −0.0624 | 0.0976 | 0.3605 | 0.030* | |
C10 | 0.1015 (3) | 0.13575 (15) | 0.41815 (5) | 0.0255 (4) | |
C11 | −0.0399 (3) | 0.28130 (17) | 0.35815 (6) | 0.0335 (4) | |
H111 | 0.0766 | 0.3437 | 0.3634 | 0.040* | |
H112 | −0.1697 | 0.2985 | 0.3778 | 0.040* | |
C12 | −0.1163 (3) | 0.28591 (18) | 0.30986 (5) | 0.0326 (4) | |
H121 | −0.1716 | 0.3681 | 0.3031 | 0.039* | |
H122 | −0.2438 | 0.2293 | 0.3057 | 0.039* | |
C13 | 0.0720 (3) | 0.25344 (15) | 0.27734 (5) | 0.0247 (3) | |
C14 | 0.1793 (3) | 0.13215 (15) | 0.29053 (5) | 0.0236 (3) | |
H14 | 0.0577 | 0.0700 | 0.2881 | 0.028* | |
C15 | 0.3596 (3) | 0.09813 (17) | 0.25715 (5) | 0.0299 (4) | |
H151 | 0.4928 | 0.1505 | 0.2618 | 0.036* | |
H152 | 0.4071 | 0.0140 | 0.2628 | 0.036* | |
C16 | 0.2862 (3) | 0.10883 (16) | 0.20965 (6) | 0.0289 (4) | |
C17A | −0.0301 (3) | 0.24112 (16) | 0.23135 (6) | 0.0274 (4) | |
C18 | 0.2448 (3) | 0.35732 (16) | 0.27420 (6) | 0.0340 (4) | |
H181 | 0.1673 | 0.4315 | 0.2653 | 0.051* | |
H182 | 0.3603 | 0.3371 | 0.2522 | 0.051* | |
H183 | 0.3164 | 0.3693 | 0.3031 | 0.051* | |
C19 | −0.0064 (4) | 0.15922 (18) | 0.15532 (5) | 0.0347 (4) | |
H191 | −0.1710 | 0.1745 | 0.1561 | 0.042* | |
H192 | 0.0168 | 0.0759 | 0.1445 | 0.042* | |
C20 | 0.1023 (3) | 0.24651 (16) | 0.12291 (6) | 0.0321 (4) | |
H201 | 0.2668 | 0.2311 | 0.1217 | 0.039* | |
H202 | 0.0795 | 0.3301 | 0.1335 | 0.039* | |
C21 | 0.0022 (4) | 0.23347 (18) | 0.07663 (6) | 0.0376 (5) | |
H211 | 0.0056 | 0.1474 | 0.0680 | 0.045* | |
H212 | −0.1577 | 0.2593 | 0.0773 | 0.045* | |
C22 | 0.1264 (4) | 0.3065 (2) | 0.04208 (6) | 0.0438 (5) | |
H221 | 0.1210 | 0.3921 | 0.0501 | 0.066* | |
H222 | 0.0546 | 0.2948 | 0.0132 | 0.066* | |
H223 | 0.2840 | 0.2799 | 0.0406 | 0.066* | |
C31 | −0.0104 (4) | 0.0507 (2) | 0.57990 (6) | 0.0463 (5) | |
H311 | −0.0353 | 0.1369 | 0.5849 | 0.069* | |
H312 | 0.0226 | 0.0111 | 0.6081 | 0.069* | |
H313 | −0.1463 | 0.0150 | 0.5669 | 0.069* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O16 | 0.0575 (9) | 0.0405 (7) | 0.0275 (6) | 0.0140 (7) | 0.0095 (7) | −0.0027 (6) |
O17A | 0.0322 (7) | 0.0562 (9) | 0.0296 (7) | 0.0108 (7) | −0.0016 (6) | 0.0077 (6) |
O31 | 0.0474 (8) | 0.0488 (8) | 0.0232 (6) | 0.0041 (7) | −0.0014 (6) | 0.0044 (6) |
N17 | 0.0318 (8) | 0.0321 (7) | 0.0226 (7) | −0.0022 (7) | −0.0008 (6) | −0.0012 (6) |
C1 | 0.0291 (9) | 0.0346 (9) | 0.0234 (8) | 0.0049 (8) | 0.0005 (7) | −0.0014 (7) |
C2 | 0.0332 (10) | 0.0360 (9) | 0.0233 (8) | 0.0029 (8) | 0.0021 (7) | −0.0029 (7) |
C3 | 0.0399 (10) | 0.0319 (9) | 0.0222 (8) | −0.0022 (8) | −0.0032 (8) | 0.0011 (7) |
C4 | 0.0318 (9) | 0.0345 (9) | 0.0289 (9) | 0.0036 (8) | −0.0047 (8) | −0.0001 (7) |
C5 | 0.0260 (9) | 0.0305 (8) | 0.0250 (8) | 0.0002 (8) | −0.0004 (7) | −0.0013 (7) |
C6 | 0.0285 (9) | 0.0432 (10) | 0.0288 (8) | 0.0107 (9) | −0.0008 (8) | 0.0001 (8) |
C7 | 0.0301 (9) | 0.0330 (9) | 0.0239 (8) | 0.0072 (8) | 0.0005 (7) | 0.0002 (7) |
C8 | 0.0220 (8) | 0.0252 (8) | 0.0239 (8) | −0.0001 (7) | 0.0002 (7) | −0.0019 (6) |
C9 | 0.0229 (8) | 0.0309 (8) | 0.0224 (8) | 0.0018 (7) | −0.0002 (7) | −0.0021 (6) |
C10 | 0.0261 (8) | 0.0288 (8) | 0.0216 (8) | −0.0002 (7) | 0.0007 (7) | −0.0011 (7) |
C11 | 0.0351 (10) | 0.0402 (10) | 0.0252 (8) | 0.0132 (9) | 0.0016 (8) | −0.0015 (8) |
C12 | 0.0316 (9) | 0.0408 (10) | 0.0256 (8) | 0.0112 (8) | 0.0010 (8) | 0.0007 (8) |
C13 | 0.0229 (8) | 0.0270 (8) | 0.0241 (8) | 0.0020 (7) | 0.0003 (7) | 0.0006 (7) |
C14 | 0.0243 (8) | 0.0254 (8) | 0.0210 (8) | −0.0015 (7) | 0.0012 (7) | −0.0002 (6) |
C15 | 0.0317 (10) | 0.0335 (9) | 0.0244 (8) | 0.0088 (8) | 0.0041 (8) | −0.0006 (7) |
C16 | 0.0338 (10) | 0.0266 (8) | 0.0264 (8) | −0.0001 (8) | 0.0036 (8) | −0.0004 (7) |
C17A | 0.0263 (9) | 0.0296 (8) | 0.0263 (8) | −0.0021 (8) | 0.0026 (7) | 0.0039 (7) |
C18 | 0.0364 (10) | 0.0278 (9) | 0.0378 (10) | −0.0031 (8) | −0.0018 (9) | 0.0024 (7) |
C19 | 0.0398 (10) | 0.0414 (10) | 0.0228 (8) | −0.0067 (9) | −0.0034 (8) | −0.0008 (7) |
C20 | 0.0342 (9) | 0.0345 (9) | 0.0275 (9) | −0.0003 (8) | −0.0005 (8) | 0.0004 (7) |
C21 | 0.0434 (11) | 0.0424 (10) | 0.0271 (9) | −0.0045 (10) | −0.0038 (9) | 0.0008 (8) |
C22 | 0.0508 (12) | 0.0529 (12) | 0.0278 (9) | −0.0080 (11) | −0.0042 (9) | 0.0043 (9) |
C31 | 0.0487 (12) | 0.0639 (14) | 0.0262 (9) | −0.0054 (12) | 0.0028 (9) | 0.0077 (9) |
Geometric parameters (Å, º) top
O16—C16 | 1.214 (2) | C11—H112 | 0.9900 |
O17A—C17A | 1.220 (2) | C12—C13 | 1.530 (2) |
O31—C3 | 1.383 (2) | C12—H121 | 0.9900 |
O31—C31 | 1.422 (3) | C12—H122 | 0.9900 |
N17—C16 | 1.397 (2) | C13—C17A | 1.522 (2) |
N17—C17A | 1.399 (2) | C13—C14 | 1.541 (2) |
N17—C19 | 1.477 (2) | C13—C18 | 1.545 (2) |
C1—C10 | 1.385 (2) | C14—C15 | 1.517 (2) |
C1—C2 | 1.392 (2) | C14—H14 | 1.0000 |
C1—H1 | 0.9500 | C15—C16 | 1.505 (2) |
C2—C3 | 1.382 (3) | C15—H151 | 0.9900 |
C2—H2 | 0.9500 | C15—H152 | 0.9900 |
C3—C4 | 1.384 (3) | C18—H181 | 0.9800 |
C4—C5 | 1.393 (2) | C18—H182 | 0.9800 |
C4—H4 | 0.9500 | C18—H183 | 0.9800 |
C5—C10 | 1.405 (2) | C19—C20 | 1.521 (2) |
C5—C6 | 1.510 (2) | C19—H191 | 0.9900 |
C6—C7 | 1.530 (2) | C19—H192 | 0.9900 |
C6—H61 | 0.9900 | C20—C21 | 1.527 (2) |
C6—H62 | 0.9900 | C20—H201 | 0.9900 |
C7—C8 | 1.525 (2) | C20—H202 | 0.9900 |
C7—H71 | 0.9900 | C21—C22 | 1.513 (3) |
C7—H72 | 0.9900 | C21—H211 | 0.9900 |
C8—C9 | 1.533 (2) | C21—H212 | 0.9900 |
C8—C14 | 1.547 (2) | C22—H221 | 0.9800 |
C8—H8 | 1.0000 | C22—H222 | 0.9800 |
C9—C10 | 1.525 (2) | C22—H223 | 0.9800 |
C9—C11 | 1.529 (2) | C31—H311 | 0.9800 |
C9—H9 | 1.0000 | C31—H312 | 0.9800 |
C11—C12 | 1.529 (2) | C31—H313 | 0.9800 |
C11—H111 | 0.9900 | | |
| | | |
C3—O31—C31 | 116.60 (16) | C17A—C13—C14 | 108.77 (13) |
C16—N17—C17A | 123.99 (14) | C12—C13—C14 | 109.90 (14) |
C16—N17—C19 | 117.14 (15) | C17A—C13—C18 | 105.90 (13) |
C17A—N17—C19 | 118.78 (15) | C12—C13—C18 | 110.31 (15) |
C10—C1—C2 | 122.80 (17) | C14—C13—C18 | 113.21 (14) |
C10—C1—H1 | 118.6 | C15—C14—C13 | 109.62 (13) |
C2—C1—H1 | 118.6 | C15—C14—C8 | 114.41 (14) |
C3—C2—C1 | 118.42 (17) | C13—C14—C8 | 112.49 (13) |
C3—C2—H2 | 120.8 | C15—C14—H14 | 106.6 |
C1—C2—H2 | 120.8 | C13—C14—H14 | 106.6 |
C2—C3—O31 | 123.51 (17) | C8—C14—H14 | 106.6 |
C2—C3—C4 | 120.11 (15) | C16—C15—C14 | 114.29 (15) |
O31—C3—C4 | 116.39 (17) | C16—C15—H151 | 108.7 |
C3—C4—C5 | 121.23 (17) | C14—C15—H151 | 108.7 |
C3—C4—H4 | 119.4 | C16—C15—H152 | 108.7 |
C5—C4—H4 | 119.4 | C14—C15—H152 | 108.7 |
C4—C5—C10 | 119.39 (16) | H151—C15—H152 | 107.6 |
C4—C5—C6 | 119.45 (16) | O16—C16—N17 | 120.31 (16) |
C10—C5—C6 | 121.15 (15) | O16—C16—C15 | 121.63 (17) |
C5—C6—C7 | 113.45 (15) | N17—C16—C15 | 118.01 (15) |
C5—C6—H61 | 108.9 | O17A—C17A—N17 | 119.96 (16) |
C7—C6—H61 | 108.9 | O17A—C17A—C13 | 122.31 (16) |
C5—C6—H62 | 108.9 | N17—C17A—C13 | 117.68 (14) |
C7—C6—H62 | 108.9 | C13—C18—H181 | 109.5 |
H61—C6—H62 | 107.7 | C13—C18—H182 | 109.5 |
C8—C7—C6 | 110.58 (14) | H181—C18—H182 | 109.5 |
C8—C7—H71 | 109.5 | C13—C18—H183 | 109.5 |
C6—C7—H71 | 109.5 | H181—C18—H183 | 109.5 |
C8—C7—H72 | 109.5 | H182—C18—H183 | 109.5 |
C6—C7—H72 | 109.5 | N17—C19—C20 | 113.64 (15) |
H71—C7—H72 | 108.1 | N17—C19—H191 | 108.8 |
C7—C8—C9 | 110.40 (14) | C20—C19—H191 | 108.8 |
C7—C8—C14 | 112.85 (13) | N17—C19—H192 | 108.8 |
C9—C8—C14 | 108.50 (13) | C20—C19—H192 | 108.8 |
C7—C8—H8 | 108.3 | H191—C19—H192 | 107.7 |
C9—C8—H8 | 108.3 | C19—C20—C21 | 111.44 (16) |
C14—C8—H8 | 108.3 | C19—C20—H201 | 109.3 |
C10—C9—C11 | 114.53 (14) | C21—C20—H201 | 109.3 |
C10—C9—C8 | 114.05 (13) | C19—C20—H202 | 109.3 |
C11—C9—C8 | 109.73 (14) | C21—C20—H202 | 109.3 |
C10—C9—H9 | 105.9 | H201—C20—H202 | 108.0 |
C11—C9—H9 | 105.9 | C22—C21—C20 | 113.13 (16) |
C8—C9—H9 | 105.9 | C22—C21—H211 | 109.0 |
C1—C10—C5 | 118.00 (15) | C20—C21—H211 | 109.0 |
C1—C10—C9 | 120.52 (15) | C22—C21—H212 | 109.0 |
C5—C10—C9 | 121.16 (15) | C20—C21—H212 | 109.0 |
C9—C11—C12 | 110.34 (15) | H211—C21—H212 | 107.8 |
C9—C11—H111 | 109.6 | C21—C22—H221 | 109.5 |
C12—C11—H111 | 109.6 | C21—C22—H222 | 109.5 |
C9—C11—H112 | 109.6 | H221—C22—H222 | 109.5 |
C12—C11—H112 | 109.6 | C21—C22—H223 | 109.5 |
H111—C11—H112 | 108.1 | H221—C22—H223 | 109.5 |
C11—C12—C13 | 112.93 (15) | H222—C22—H223 | 109.5 |
C11—C12—H121 | 109.0 | O31—C31—H311 | 109.5 |
C13—C12—H121 | 109.0 | O31—C31—H312 | 109.5 |
C11—C12—H122 | 109.0 | H311—C31—H312 | 109.5 |
C13—C12—H122 | 109.0 | O31—C31—H313 | 109.5 |
H121—C12—H122 | 107.8 | H311—C31—H313 | 109.5 |
C17A—C13—C12 | 108.58 (14) | H312—C31—H313 | 109.5 |
| | | |
C10—C1—C2—C3 | 0.7 (3) | C11—C12—C13—C18 | −73.3 (2) |
C1—C2—C3—O31 | −178.07 (17) | C17A—C13—C14—C15 | 59.07 (18) |
C1—C2—C3—C4 | 1.7 (3) | C12—C13—C14—C15 | 177.82 (15) |
C31—O31—C3—C2 | 13.2 (3) | C18—C13—C14—C15 | −58.35 (18) |
C31—O31—C3—C4 | −166.53 (18) | C17A—C13—C14—C8 | −172.44 (13) |
C2—C3—C4—C5 | −2.6 (3) | C12—C13—C14—C8 | −53.69 (18) |
O31—C3—C4—C5 | 177.14 (17) | C18—C13—C14—C8 | 70.14 (18) |
C3—C4—C5—C10 | 1.2 (3) | C7—C8—C14—C15 | −53.0 (2) |
C3—C4—C5—C6 | −178.21 (17) | C9—C8—C14—C15 | −175.66 (14) |
C4—C5—C6—C7 | 156.94 (17) | C7—C8—C14—C13 | −178.93 (14) |
C10—C5—C6—C7 | −22.5 (3) | C9—C8—C14—C13 | 58.40 (18) |
C5—C6—C7—C8 | 49.3 (2) | C13—C14—C15—C16 | −48.1 (2) |
C6—C7—C8—C9 | −61.13 (19) | C8—C14—C15—C16 | −175.54 (15) |
C6—C7—C8—C14 | 177.26 (14) | C17A—N17—C16—O16 | −168.26 (17) |
C7—C8—C9—C10 | 45.21 (19) | C19—N17—C16—O16 | 8.1 (2) |
C14—C8—C9—C10 | 169.36 (14) | C17A—N17—C16—C15 | 14.4 (2) |
C7—C8—C9—C11 | 175.22 (14) | C19—N17—C16—C15 | −169.19 (16) |
C14—C8—C9—C11 | −60.63 (18) | C14—C15—C16—O16 | −165.48 (17) |
C2—C1—C10—C5 | −2.0 (3) | C14—C15—C16—N17 | 11.8 (2) |
C2—C1—C10—C9 | 171.44 (17) | C16—N17—C17A—O17A | 176.58 (16) |
C4—C5—C10—C1 | 1.1 (3) | C19—N17—C17A—O17A | 0.3 (2) |
C6—C5—C10—C1 | −179.51 (16) | C16—N17—C17A—C13 | −1.1 (2) |
C4—C5—C10—C9 | −172.36 (16) | C19—N17—C17A—C13 | −177.45 (15) |
C6—C5—C10—C9 | 7.0 (3) | C12—C13—C17A—O17A | 26.9 (2) |
C11—C9—C10—C1 | 40.5 (2) | C14—C13—C17A—O17A | 146.48 (17) |
C8—C9—C10—C1 | 168.08 (16) | C18—C13—C17A—O17A | −91.55 (18) |
C11—C9—C10—C5 | −146.23 (17) | C12—C13—C17A—N17 | −155.44 (16) |
C8—C9—C10—C5 | −18.6 (2) | C14—C13—C17A—N17 | −35.9 (2) |
C10—C9—C11—C12 | −170.27 (15) | C18—C13—C17A—N17 | 86.10 (18) |
C8—C9—C11—C12 | 59.98 (19) | C16—N17—C19—C20 | −81.5 (2) |
C9—C11—C12—C13 | −56.1 (2) | C17A—N17—C19—C20 | 95.0 (2) |
C11—C12—C13—C17A | 171.04 (15) | N17—C19—C20—C21 | −179.68 (16) |
C11—C12—C13—C14 | 52.2 (2) | C19—C20—C21—C22 | −172.31 (18) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H121···O16i | 0.99 | 2.59 | 3.504 (2) | 154 |
C31—H312···O16ii | 0.98 | 2.37 | 3.347 (2) | 174 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1/2, −y, z+1/2. |
Matrix of r.m.s. deviations (Å) for the superposition of the non-H atoms
common to the structures of (I)–(VI). topCompound | (I) | (II) | (III) | (IV) | (V) |
(II) | 0.57 | | | | |
(III) | 0.25 | 0.32 | | | |
(IV) | 0.24 | 0.23 | 0.06 | | |
(V) | 0.13 | 0.19 | 0.37 | 0.09 | |
(VI) | 0.21 | 0.21 | 0.40 | 0.18 | 0.16 |