Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807025020/sg2168sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807025020/sg2168Isup2.hkl |
CCDC reference: 651516
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.037
- wR factor = 0.099
- Data-to-parameter ratio = 7.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.89 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C16 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C17 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C16 - C17 ... 1.42 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 2225 Count of symmetry unique reflns 2225 Completeness (_total/calc) 100.00% 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 PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 7 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 0 ALERT type 5 Informative message, check
For related literature, see: Alvarez-Ginarte et al. (2005); Cremer & Pople (1975).
17-hydroxy-13-methyl-1,7,8,10,11,12,13,15,16,17-decahydro-2H- cyclopenta[a]phenanthren-3(6H,9H,14H)-one (2.74 g, 10 mmol) and pyridine (20 mmol) were added to CH2Cl2 (20 ml) with stirring. 4-nitrobenzoyl chloride (1.86 g, 10 mmol) in CH2Cl2 (10 ml) was added dropwise over 15 minutes. The mixture was stirred at room temperature for 3 h and filtered. The filtrate was concentrated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with petroleum ether (303–333 K)-diethyl ether, to give the product as a pale-yellow solid (1.28 g, 30.2%). A solution of the compound in ethanol was concentrated gradually at room temperature to afford colourless prisms (m.p. 472–475 K).
H atoms were added at calculated positions and refined using a riding model. H atoms were given isotropic displacement parameters equal to 1.2(or 1.5 for methyl H atoms) times the equivalent isotropic displacement parameters of their parent atoms, with C—H distances of 0.96 (Cmethyl), 0.97 (Cmethylene), 0.98 (Cmethine) and 0.93 Å (Caromatic). In the absence of significant anomalous dispersion effects, Friedel pairs were averaged. The absolute configuration was assigned arbitrarily.
Testosterone derivatives exhibit a high level of biological activity and have been widely used as hormone treatments (Alvarez-Ginarte et al., 2005). 13-Methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro- 1H-cyclopenta[a]phenanthren-17-yl 4-nitrobenzoate, (I), was obtained from the reaction of 4-nitrobenzoyl chloride and 17-hydroxy-13-methyl- 1,7,8,10,11,12,13,15,16,17-decahydro-2H-cyclopenta[a]phenanthren- 3(6H,9H,14H)-one, as colorless crystals suitable for X-ray crystallographic analysis.
The molecular structure of (I) is built up from three six-membered and one five-membered fused rings. (Fig. 1). The C11—C14/C7/C6 and C3—C6/C14/C15 rings have chair conformations (Cremer & Pople, 1975). The dihedral angles between the C6/C7/C12/C13 and C4/C5/C14/C15 planes is 1.91 (23) o. Atoms C10, C19, C20, C21, C22, C23, C24, C25, O2, O5 and N1 are coplanar to within 0.0848 Å, and atoms O3 and O4 deviate from this plane by -0.2783 (40) and -0.1457 (48) Å, respectively.
For related literature, see: Alvarez-Ginarte et al. (2005); Cremer & Pople (1975).
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Version 1.05; Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C25H29NO5 | Dx = 1.268 Mg m−3 |
Mr = 423.49 | Melting point = 472–475 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 10.8866 (6) Å | θ = 10.0–14.8° |
b = 11.5321 (6) Å | µ = 0.09 mm−1 |
c = 17.6671 (9) Å | T = 298 K |
V = 2218.0 (2) Å3 | Prism, colourless |
Z = 4 | 0.32 × 0.21 × 0.12 mm |
F(000) = 904 |
Enraf-Nonius CAD-4 diffractometer | 1757 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.042 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
ω/2–θ scans | h = −12→12 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −13→11 |
Tmin = 0.964, Tmax = 0.990 | l = −21→21 |
25354 measured reflections | 3 standard reflections every 60 min |
2225 independent reflections | intensity decay: 0.3% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0431P)2 + 0.439P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.099 | (Δ/σ)max = 0.001 |
S = 1.03 | Δρmax = 0.21 e Å−3 |
2225 reflections | Δρmin = −0.13 e Å−3 |
282 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0045 (9) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map |
C25H29NO5 | V = 2218.0 (2) Å3 |
Mr = 423.49 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 10.8866 (6) Å | µ = 0.09 mm−1 |
b = 11.5321 (6) Å | T = 298 K |
c = 17.6671 (9) Å | 0.32 × 0.21 × 0.12 mm |
Enraf-Nonius CAD-4 diffractometer | 1757 reflections with I > 2σ(I) |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | Rint = 0.042 |
Tmin = 0.964, Tmax = 0.990 | 3 standard reflections every 60 min |
25354 measured reflections | intensity decay: 0.3% |
2225 independent reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.21 e Å−3 |
2225 reflections | Δρmin = −0.13 e Å−3 |
282 parameters | Absolute structure: Flack (1983) |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.5768 (3) | 0.6312 (3) | 0.42364 (14) | 0.1174 (10) | |
O2 | 0.4737 (2) | 0.51962 (18) | 1.01883 (11) | 0.0694 (6) | |
O3 | 0.5297 (3) | 0.6795 (2) | 1.08166 (12) | 0.0873 (7) | |
O4 | 0.6884 (3) | 0.1759 (3) | 1.30309 (17) | 0.1259 (12) | |
O5 | 0.7028 (3) | 0.3232 (3) | 1.37676 (16) | 0.1229 (12) | |
N1 | 0.6778 (3) | 0.2788 (3) | 1.31684 (18) | 0.0888 (9) | |
C1 | 0.5414 (4) | 0.5881 (3) | 0.48331 (19) | 0.0869 (10) | |
C2 | 0.4313 (3) | 0.6266 (3) | 0.52155 (16) | 0.0694 (8) | |
H2 | 0.3846 | 0.6845 | 0.4989 | 0.083* | |
C3 | 0.3929 (3) | 0.5836 (3) | 0.58751 (15) | 0.0605 (7) | |
C4 | 0.2712 (3) | 0.6168 (3) | 0.62039 (17) | 0.0730 (9) | |
H4A | 0.2157 | 0.5512 | 0.6172 | 0.088* | |
H4B | 0.2364 | 0.6797 | 0.5910 | 0.088* | |
C5 | 0.2828 (3) | 0.6547 (3) | 0.70291 (16) | 0.0671 (8) | |
H5A | 0.3268 | 0.7278 | 0.7052 | 0.081* | |
H5B | 0.2014 | 0.6670 | 0.7238 | 0.081* | |
C6 | 0.3497 (3) | 0.5657 (2) | 0.75022 (15) | 0.0552 (7) | |
H6 | 0.3006 | 0.4945 | 0.7509 | 0.066* | |
C7 | 0.3685 (3) | 0.6050 (3) | 0.83138 (15) | 0.0590 (7) | |
H7 | 0.4229 | 0.6725 | 0.8284 | 0.071* | |
C8 | 0.2595 (3) | 0.6435 (4) | 0.87880 (18) | 0.0820 (10) | |
H8A | 0.1906 | 0.5910 | 0.8726 | 0.098* | |
H8B | 0.2337 | 0.7213 | 0.8651 | 0.098* | |
C9 | 0.3092 (3) | 0.6400 (3) | 0.96115 (18) | 0.0824 (10) | |
H9A | 0.3118 | 0.7172 | 0.9828 | 0.099* | |
H9B | 0.2580 | 0.5911 | 0.9928 | 0.099* | |
C10 | 0.4384 (3) | 0.5895 (3) | 0.95376 (15) | 0.0671 (8) | |
H10 | 0.4975 | 0.6529 | 0.9475 | 0.081* | |
C11 | 0.4355 (3) | 0.5171 (2) | 0.88165 (15) | 0.0576 (7) | |
C12 | 0.5594 (3) | 0.4892 (3) | 0.84696 (16) | 0.0742 (9) | |
H12A | 0.5988 | 0.4284 | 0.8761 | 0.089* | |
H12B | 0.6114 | 0.5575 | 0.8490 | 0.089* | |
C13 | 0.5457 (3) | 0.4499 (3) | 0.76461 (16) | 0.0727 (9) | |
H13A | 0.6266 | 0.4379 | 0.7431 | 0.087* | |
H13B | 0.5027 | 0.3762 | 0.7635 | 0.087* | |
C14 | 0.4756 (3) | 0.5373 (3) | 0.71588 (15) | 0.0588 (7) | |
H14 | 0.5233 | 0.6093 | 0.7165 | 0.071* | |
C15 | 0.4674 (3) | 0.4983 (3) | 0.63285 (16) | 0.0677 (8) | |
H15 | 0.4254 | 0.4232 | 0.6314 | 0.081* | |
C16 | 0.5959 (4) | 0.4828 (5) | 0.5982 (2) | 0.1153 (17) | |
H16A | 0.6489 | 0.5429 | 0.6184 | 0.138* | |
H16B | 0.6284 | 0.4089 | 0.6152 | 0.138* | |
C17 | 0.6043 (5) | 0.4862 (5) | 0.5178 (2) | 0.1240 (18) | |
H17A | 0.5685 | 0.4158 | 0.4973 | 0.149* | |
H17B | 0.6902 | 0.4876 | 0.5034 | 0.149* | |
C18 | 0.3607 (3) | 0.4057 (3) | 0.89454 (18) | 0.0748 (9) | |
H18A | 0.3478 | 0.3673 | 0.8470 | 0.112* | |
H18B | 0.2828 | 0.4251 | 0.9166 | 0.112* | |
H18C | 0.4049 | 0.3551 | 0.9280 | 0.112* | |
C19 | 0.5181 (3) | 0.5761 (3) | 1.07838 (16) | 0.0619 (7) | |
C20 | 0.5542 (3) | 0.4962 (3) | 1.14058 (15) | 0.0575 (7) | |
C21 | 0.5865 (3) | 0.5425 (3) | 1.21044 (17) | 0.0690 (8) | |
H21 | 0.5827 | 0.6223 | 1.2177 | 0.083* | |
C22 | 0.6237 (3) | 0.4725 (3) | 1.26874 (18) | 0.0730 (9) | |
H22 | 0.6444 | 0.5037 | 1.3156 | 0.088* | |
C23 | 0.6298 (3) | 0.3553 (3) | 1.25628 (17) | 0.0692 (8) | |
C24 | 0.5963 (3) | 0.3054 (3) | 1.18887 (17) | 0.0721 (9) | |
H24 | 0.5996 | 0.2255 | 1.1823 | 0.087* | |
C25 | 0.5576 (3) | 0.3771 (3) | 1.13105 (17) | 0.0673 (8) | |
H25 | 0.5334 | 0.3450 | 1.0851 | 0.081* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.159 (3) | 0.108 (2) | 0.0856 (17) | 0.012 (2) | 0.0421 (18) | 0.0313 (16) |
O2 | 0.0882 (15) | 0.0667 (13) | 0.0533 (11) | −0.0137 (12) | −0.0126 (11) | −0.0002 (10) |
O3 | 0.1123 (19) | 0.0689 (14) | 0.0806 (14) | −0.0207 (14) | −0.0277 (14) | −0.0006 (12) |
O4 | 0.163 (3) | 0.110 (2) | 0.104 (2) | 0.058 (2) | 0.003 (2) | 0.0158 (19) |
O5 | 0.165 (3) | 0.125 (2) | 0.0785 (17) | −0.045 (2) | −0.0390 (18) | 0.0294 (17) |
N1 | 0.088 (2) | 0.103 (3) | 0.075 (2) | 0.001 (2) | −0.0039 (17) | 0.0159 (19) |
C1 | 0.107 (3) | 0.083 (2) | 0.070 (2) | 0.003 (2) | 0.012 (2) | 0.0148 (19) |
C2 | 0.082 (2) | 0.0657 (19) | 0.0599 (17) | −0.0003 (18) | −0.0080 (16) | 0.0069 (16) |
C3 | 0.0682 (18) | 0.0609 (17) | 0.0522 (16) | −0.0072 (16) | −0.0090 (14) | 0.0021 (14) |
C4 | 0.0680 (19) | 0.086 (2) | 0.0650 (18) | 0.0065 (18) | −0.0126 (15) | 0.0062 (18) |
C5 | 0.0616 (18) | 0.073 (2) | 0.0664 (18) | 0.0098 (16) | −0.0093 (15) | −0.0032 (16) |
C6 | 0.0535 (15) | 0.0537 (16) | 0.0583 (16) | −0.0012 (13) | −0.0051 (13) | 0.0011 (13) |
C7 | 0.0609 (17) | 0.0580 (17) | 0.0582 (16) | −0.0039 (14) | −0.0051 (14) | −0.0029 (14) |
C8 | 0.084 (2) | 0.093 (2) | 0.069 (2) | 0.023 (2) | −0.0012 (18) | −0.0100 (19) |
C9 | 0.104 (3) | 0.079 (2) | 0.0640 (19) | 0.017 (2) | 0.0001 (19) | −0.0116 (17) |
C10 | 0.084 (2) | 0.0626 (18) | 0.0547 (16) | −0.0082 (17) | −0.0088 (16) | 0.0023 (14) |
C11 | 0.0620 (17) | 0.0588 (16) | 0.0520 (15) | −0.0055 (14) | −0.0008 (14) | −0.0005 (13) |
C12 | 0.0649 (19) | 0.093 (2) | 0.0649 (18) | 0.0100 (19) | −0.0058 (16) | 0.0130 (17) |
C13 | 0.0654 (18) | 0.092 (2) | 0.0603 (18) | 0.0240 (17) | 0.0034 (16) | 0.0112 (16) |
C14 | 0.0567 (16) | 0.0630 (17) | 0.0566 (15) | −0.0011 (14) | −0.0036 (14) | 0.0069 (14) |
C15 | 0.080 (2) | 0.0688 (19) | 0.0547 (16) | 0.0097 (17) | 0.0063 (16) | 0.0094 (15) |
C16 | 0.111 (3) | 0.164 (4) | 0.072 (2) | 0.061 (3) | 0.027 (2) | 0.032 (3) |
C17 | 0.135 (4) | 0.141 (4) | 0.096 (3) | 0.049 (3) | 0.042 (3) | 0.045 (3) |
C18 | 0.094 (2) | 0.0658 (19) | 0.0640 (18) | −0.0165 (18) | 0.0028 (17) | −0.0028 (16) |
C19 | 0.0582 (17) | 0.071 (2) | 0.0569 (16) | −0.0101 (16) | −0.0024 (14) | −0.0061 (15) |
C20 | 0.0537 (16) | 0.0661 (18) | 0.0527 (15) | −0.0036 (14) | −0.0029 (13) | −0.0052 (14) |
C21 | 0.0726 (19) | 0.0699 (19) | 0.0645 (18) | −0.0074 (16) | −0.0075 (16) | −0.0082 (16) |
C22 | 0.074 (2) | 0.085 (2) | 0.0596 (18) | −0.0061 (18) | −0.0081 (16) | −0.0034 (17) |
C23 | 0.0625 (18) | 0.080 (2) | 0.0647 (19) | 0.0009 (17) | −0.0020 (15) | 0.0075 (17) |
C24 | 0.075 (2) | 0.0687 (19) | 0.072 (2) | 0.0060 (18) | −0.0014 (17) | −0.0054 (17) |
C25 | 0.0710 (19) | 0.0702 (19) | 0.0605 (17) | −0.0008 (17) | −0.0026 (16) | −0.0087 (16) |
O1—C1 | 1.228 (4) | C10—H10 | 0.9800 |
O2—C19 | 1.328 (3) | C11—C12 | 1.516 (4) |
O2—C10 | 1.455 (3) | C11—C18 | 1.538 (4) |
O3—C19 | 1.201 (4) | C12—C13 | 1.531 (4) |
O4—N1 | 1.217 (4) | C12—H12A | 0.9700 |
O5—N1 | 1.207 (4) | C12—H12B | 0.9700 |
N1—C23 | 1.482 (4) | C13—C14 | 1.530 (4) |
C1—C2 | 1.446 (5) | C13—H13A | 0.9700 |
C1—C17 | 1.490 (6) | C13—H13B | 0.9700 |
C2—C3 | 1.333 (4) | C14—C15 | 1.537 (4) |
C2—H2 | 0.9300 | C14—H14 | 0.9800 |
C3—C4 | 1.496 (4) | C15—C16 | 1.538 (5) |
C3—C15 | 1.505 (4) | C15—H15 | 0.9800 |
C4—C5 | 1.527 (4) | C16—C17 | 1.424 (5) |
C4—H4A | 0.9700 | C16—H16A | 0.9700 |
C4—H4B | 0.9700 | C16—H16B | 0.9700 |
C5—C6 | 1.511 (4) | C17—H17A | 0.9700 |
C5—H5A | 0.9700 | C17—H17B | 0.9700 |
C5—H5B | 0.9700 | C18—H18A | 0.9600 |
C6—C7 | 1.518 (4) | C18—H18B | 0.9600 |
C6—C14 | 1.535 (4) | C18—H18C | 0.9600 |
C6—H6 | 0.9800 | C19—C20 | 1.487 (4) |
C7—C8 | 1.520 (4) | C20—C25 | 1.384 (4) |
C7—C11 | 1.532 (4) | C20—C21 | 1.390 (4) |
C7—H7 | 0.9800 | C21—C22 | 1.370 (4) |
C8—C9 | 1.553 (5) | C21—H21 | 0.9300 |
C8—H8A | 0.9700 | C22—C23 | 1.371 (5) |
C8—H8B | 0.9700 | C22—H22 | 0.9300 |
C9—C10 | 1.529 (5) | C23—C24 | 1.372 (4) |
C9—H9A | 0.9700 | C24—C25 | 1.380 (4) |
C9—H9B | 0.9700 | C24—H24 | 0.9300 |
C10—C11 | 1.524 (4) | C25—H25 | 0.9300 |
C19—O2—C10 | 116.8 (2) | C11—C12—H12A | 109.4 |
O5—N1—O4 | 124.6 (3) | C13—C12—H12A | 109.4 |
O5—N1—C23 | 117.4 (3) | C11—C12—H12B | 109.4 |
O4—N1—C23 | 118.0 (3) | C13—C12—H12B | 109.4 |
O1—C1—C2 | 122.5 (4) | H12A—C12—H12B | 108.0 |
O1—C1—C17 | 121.8 (4) | C14—C13—C12 | 112.8 (3) |
C2—C1—C17 | 115.6 (3) | C14—C13—H13A | 109.0 |
C3—C2—C1 | 123.6 (3) | C12—C13—H13A | 109.0 |
C3—C2—H2 | 118.2 | C14—C13—H13B | 109.0 |
C1—C2—H2 | 118.2 | C12—C13—H13B | 109.0 |
C2—C3—C4 | 121.4 (3) | H13A—C13—H13B | 107.8 |
C2—C3—C15 | 122.6 (3) | C13—C14—C6 | 111.3 (2) |
C4—C3—C15 | 116.0 (3) | C13—C14—C15 | 111.9 (2) |
C3—C4—C5 | 111.8 (3) | C6—C14—C15 | 112.8 (2) |
C3—C4—H4A | 109.3 | C13—C14—H14 | 106.8 |
C5—C4—H4A | 109.3 | C6—C14—H14 | 106.8 |
C3—C4—H4B | 109.3 | C15—C14—H14 | 106.8 |
C5—C4—H4B | 109.3 | C3—C15—C14 | 110.4 (2) |
H4A—C4—H4B | 107.9 | C3—C15—C16 | 110.8 (3) |
C6—C5—C4 | 111.9 (3) | C14—C15—C16 | 111.2 (3) |
C6—C5—H5A | 109.2 | C3—C15—H15 | 108.1 |
C4—C5—H5A | 109.2 | C14—C15—H15 | 108.1 |
C6—C5—H5B | 109.2 | C16—C15—H15 | 108.1 |
C4—C5—H5B | 109.2 | C17—C16—C15 | 116.9 (4) |
H5A—C5—H5B | 107.9 | C17—C16—H16A | 108.1 |
C5—C6—C7 | 112.6 (2) | C15—C16—H16A | 108.1 |
C5—C6—C14 | 110.9 (2) | C17—C16—H16B | 108.1 |
C7—C6—C14 | 108.4 (2) | C15—C16—H16B | 108.1 |
C5—C6—H6 | 108.2 | H16A—C16—H16B | 107.3 |
C7—C6—H6 | 108.2 | C16—C17—C1 | 113.6 (4) |
C14—C6—H6 | 108.2 | C16—C17—H17A | 108.9 |
C6—C7—C8 | 120.2 (2) | C1—C17—H17A | 108.9 |
C6—C7—C11 | 114.5 (2) | C16—C17—H17B | 108.9 |
C8—C7—C11 | 104.2 (2) | C1—C17—H17B | 108.9 |
C6—C7—H7 | 105.6 | H17A—C17—H17B | 107.7 |
C8—C7—H7 | 105.6 | C11—C18—H18A | 109.5 |
C11—C7—H7 | 105.6 | C11—C18—H18B | 109.5 |
C7—C8—C9 | 103.7 (3) | H18A—C18—H18B | 109.5 |
C7—C8—H8A | 111.0 | C11—C18—H18C | 109.5 |
C9—C8—H8A | 111.0 | H18A—C18—H18C | 109.5 |
C7—C8—H8B | 111.0 | H18B—C18—H18C | 109.5 |
C9—C8—H8B | 111.0 | O3—C19—O2 | 124.3 (3) |
H8A—C8—H8B | 109.0 | O3—C19—C20 | 123.5 (3) |
C10—C9—C8 | 104.5 (3) | O2—C19—C20 | 112.2 (3) |
C10—C9—H9A | 110.8 | C25—C20—C21 | 118.8 (3) |
C8—C9—H9A | 110.8 | C25—C20—C19 | 122.1 (3) |
C10—C9—H9B | 110.8 | C21—C20—C19 | 119.0 (3) |
C8—C9—H9B | 110.8 | C22—C21—C20 | 121.1 (3) |
H9A—C9—H9B | 108.9 | C22—C21—H21 | 119.5 |
O2—C10—C11 | 111.3 (2) | C20—C21—H21 | 119.5 |
O2—C10—C9 | 112.7 (3) | C21—C22—C23 | 118.3 (3) |
C11—C10—C9 | 105.1 (3) | C21—C22—H22 | 120.8 |
O2—C10—H10 | 109.2 | C23—C22—H22 | 120.8 |
C11—C10—H10 | 109.2 | C22—C23—C24 | 122.7 (3) |
C9—C10—H10 | 109.2 | C22—C23—N1 | 119.2 (3) |
C12—C11—C10 | 115.8 (3) | C24—C23—N1 | 118.1 (3) |
C12—C11—C7 | 109.2 (2) | C23—C24—C25 | 118.2 (3) |
C10—C11—C7 | 97.6 (2) | C23—C24—H24 | 120.9 |
C12—C11—C18 | 110.7 (3) | C25—C24—H24 | 120.9 |
C10—C11—C18 | 110.2 (2) | C24—C25—C20 | 120.8 (3) |
C7—C11—C18 | 112.7 (2) | C24—C25—H25 | 119.6 |
C11—C12—C13 | 111.1 (3) | C20—C25—H25 | 119.6 |
O1—C1—C2—C3 | −177.9 (4) | C5—C6—C14—C13 | 178.3 (2) |
C17—C1—C2—C3 | 6.7 (5) | C7—C6—C14—C13 | 54.2 (3) |
C1—C2—C3—C4 | −173.0 (3) | C5—C6—C14—C15 | −54.8 (3) |
C1—C2—C3—C15 | 6.2 (5) | C7—C6—C14—C15 | −179.0 (2) |
C2—C3—C4—C5 | −129.9 (3) | C2—C3—C15—C14 | 131.2 (3) |
C15—C3—C4—C5 | 50.8 (4) | C4—C3—C15—C14 | −49.6 (4) |
C3—C4—C5—C6 | −52.5 (4) | C2—C3—C15—C16 | 7.6 (4) |
C4—C5—C6—C7 | 176.7 (2) | C4—C3—C15—C16 | −173.2 (3) |
C4—C5—C6—C14 | 54.9 (3) | C13—C14—C15—C3 | 177.3 (3) |
C5—C6—C7—C8 | 54.5 (4) | C6—C14—C15—C3 | 50.9 (3) |
C14—C6—C7—C8 | 177.6 (3) | C13—C14—C15—C16 | −59.3 (4) |
C5—C6—C7—C11 | 179.7 (2) | C6—C14—C15—C16 | 174.2 (3) |
C14—C6—C7—C11 | −57.2 (3) | C3—C15—C16—C17 | −36.0 (6) |
C6—C7—C8—C9 | 163.5 (3) | C14—C15—C16—C17 | −159.1 (4) |
C11—C7—C8—C9 | 33.6 (3) | C15—C16—C17—C1 | 49.8 (7) |
C7—C8—C9—C10 | −4.8 (4) | O1—C1—C17—C16 | 150.3 (5) |
C19—O2—C10—C11 | 158.7 (3) | C2—C1—C17—C16 | −34.2 (6) |
C19—O2—C10—C9 | −83.5 (3) | C10—O2—C19—O3 | 0.5 (5) |
C8—C9—C10—O2 | −147.1 (3) | C10—O2—C19—C20 | −178.4 (2) |
C8—C9—C10—C11 | −25.7 (4) | O3—C19—C20—C25 | −169.9 (3) |
O2—C10—C11—C12 | −76.9 (3) | O2—C19—C20—C25 | 9.1 (4) |
C9—C10—C11—C12 | 160.8 (3) | O3—C19—C20—C21 | 9.7 (5) |
O2—C10—C11—C7 | 167.4 (2) | O2—C19—C20—C21 | −171.3 (3) |
C9—C10—C11—C7 | 45.1 (3) | C25—C20—C21—C22 | 1.5 (5) |
O2—C10—C11—C18 | 49.8 (3) | C19—C20—C21—C22 | −178.1 (3) |
C9—C10—C11—C18 | −72.5 (3) | C20—C21—C22—C23 | 0.7 (5) |
C6—C7—C11—C12 | 57.5 (3) | C21—C22—C23—C24 | −2.2 (5) |
C8—C7—C11—C12 | −169.2 (3) | C21—C22—C23—N1 | 175.9 (3) |
C6—C7—C11—C10 | 178.3 (2) | O5—N1—C23—C22 | 4.4 (5) |
C8—C7—C11—C10 | −48.4 (3) | O4—N1—C23—C22 | −176.2 (4) |
C6—C7—C11—C18 | −66.0 (3) | O5—N1—C23—C24 | −177.4 (3) |
C8—C7—C11—C18 | 67.3 (3) | O4—N1—C23—C24 | 2.0 (5) |
C10—C11—C12—C13 | −162.8 (3) | C22—C23—C24—C25 | 1.4 (5) |
C7—C11—C12—C13 | −53.8 (3) | N1—C23—C24—C25 | −176.7 (3) |
C18—C11—C12—C13 | 70.9 (3) | C23—C24—C25—C20 | 0.8 (5) |
C11—C12—C13—C14 | 54.8 (4) | C21—C20—C25—C24 | −2.2 (5) |
C12—C13—C14—C6 | −55.0 (3) | C19—C20—C25—C24 | 177.3 (3) |
C12—C13—C14—C15 | 177.7 (3) |
Experimental details
Crystal data | |
Chemical formula | C25H29NO5 |
Mr | 423.49 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 298 |
a, b, c (Å) | 10.8866 (6), 11.5321 (6), 17.6671 (9) |
V (Å3) | 2218.0 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.32 × 0.21 × 0.12 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.964, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25354, 2225, 1757 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.099, 1.03 |
No. of reflections | 2225 |
No. of parameters | 282 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.13 |
Absolute structure | Flack (1983) |
Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Version 1.05; Farrugia, 1997), WinGX (Farrugia, 1999).
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Testosterone derivatives exhibit a high level of biological activity and have been widely used as hormone treatments (Alvarez-Ginarte et al., 2005). 13-Methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro- 1H-cyclopenta[a]phenanthren-17-yl 4-nitrobenzoate, (I), was obtained from the reaction of 4-nitrobenzoyl chloride and 17-hydroxy-13-methyl- 1,7,8,10,11,12,13,15,16,17-decahydro-2H-cyclopenta[a]phenanthren- 3(6H,9H,14H)-one, as colorless crystals suitable for X-ray crystallographic analysis.
The molecular structure of (I) is built up from three six-membered and one five-membered fused rings. (Fig. 1). The C11—C14/C7/C6 and C3—C6/C14/C15 rings have chair conformations (Cremer & Pople, 1975). The dihedral angles between the C6/C7/C12/C13 and C4/C5/C14/C15 planes is 1.91 (23) o. Atoms C10, C19, C20, C21, C22, C23, C24, C25, O2, O5 and N1 are coplanar to within 0.0848 Å, and atoms O3 and O4 deviate from this plane by -0.2783 (40) and -0.1457 (48) Å, respectively.