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In the title compound, C23H31NO3, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027042/hg6236sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027042/hg6236Isup2.hkl
Contains datablock I

CCDC reference: 285511

Key indicators

  • Single-crystal X-ray study
  • T = 160 K
  • Mean [sigma](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

Computing details top

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-16,17a-dione top
Crystal data top
C23H31NO3F(000) = 800
Mr = 369.49Dx = 1.235 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3360 reflections
a = 5.9243 (1) Åθ = 2.0–30.0°
b = 11.0968 (3) ŵ = 0.08 mm1
c = 30.2328 (7) ÅT = 160 K
V = 1987.53 (8) Å3Prism, colourless
Z = 40.30 × 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 generatorRint = 0.059
Horizontally mounted graphite crystal monochromatorθmax = 30.0°, θmin = 2.7°
Detector resolution: 9 pixels mm-1h = 88
φ and ω scans with κ offsetsk = 1515
34883 measured reflectionsl = 4242
3343 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-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 reflectionsΔρmax = 0.21 e Å3
247 parametersΔρmin = 0.20 e Å3
0 restraintsAbsolute 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
xyzUiso*/Ueq
O160.3938 (3)0.06338 (12)0.17981 (4)0.0418 (4)
O17A0.2008 (2)0.29479 (14)0.22033 (4)0.0393 (3)
O310.1749 (2)0.03477 (13)0.55058 (4)0.0398 (3)
N170.0836 (3)0.16860 (14)0.20074 (4)0.0289 (3)
C10.0499 (3)0.17622 (17)0.44974 (5)0.0290 (4)
H10.17060.22680.44060.035*
C20.0327 (3)0.14596 (17)0.49430 (5)0.0309 (4)
H20.14020.17450.51510.037*
C30.1445 (3)0.07343 (16)0.50751 (5)0.0313 (4)
C40.3031 (3)0.03514 (17)0.47697 (5)0.0317 (4)
H40.42760.01190.48660.038*
C50.2834 (3)0.06427 (15)0.43233 (5)0.0272 (4)
C60.4565 (3)0.01755 (19)0.39995 (5)0.0335 (4)
H610.50400.06420.40920.040*
H620.59110.07030.40100.040*
C70.3702 (3)0.01175 (16)0.35230 (5)0.0290 (4)
H710.49770.00550.33210.035*
H720.25920.05450.34950.035*
C80.2597 (3)0.13068 (15)0.33920 (5)0.0237 (3)
H80.37280.19670.34320.028*
C90.0567 (3)0.15701 (16)0.36911 (5)0.0254 (4)
H90.06240.09760.36050.030*
C100.1015 (3)0.13575 (15)0.41815 (5)0.0255 (4)
C110.0399 (3)0.28130 (17)0.35815 (6)0.0335 (4)
H1110.07660.34370.36340.040*
H1120.16970.29850.37780.040*
C120.1163 (3)0.28591 (18)0.30986 (5)0.0326 (4)
H1210.17160.36810.30310.039*
H1220.24380.22930.30570.039*
C130.0720 (3)0.25344 (15)0.27734 (5)0.0247 (3)
C140.1793 (3)0.13215 (15)0.29053 (5)0.0236 (3)
H140.05770.07000.28810.028*
C150.3596 (3)0.09813 (17)0.25715 (5)0.0299 (4)
H1510.49280.15050.26180.036*
H1520.40710.01400.26280.036*
C160.2862 (3)0.10883 (16)0.20965 (6)0.0289 (4)
C17A0.0301 (3)0.24112 (16)0.23135 (6)0.0274 (4)
C180.2448 (3)0.35732 (16)0.27420 (6)0.0340 (4)
H1810.16730.43150.26530.051*
H1820.36030.33710.25220.051*
H1830.31640.36930.30310.051*
C190.0064 (4)0.15922 (18)0.15532 (5)0.0347 (4)
H1910.17100.17450.15610.042*
H1920.01680.07590.14450.042*
C200.1023 (3)0.24651 (16)0.12291 (6)0.0321 (4)
H2010.26680.23110.12170.039*
H2020.07950.33010.13350.039*
C210.0022 (4)0.23347 (18)0.07663 (6)0.0376 (5)
H2110.00560.14740.06800.045*
H2120.15770.25930.07730.045*
C220.1264 (4)0.3065 (2)0.04208 (6)0.0438 (5)
H2210.12100.39210.05010.066*
H2220.05460.29480.01320.066*
H2230.28400.27990.04060.066*
C310.0104 (4)0.0507 (2)0.57990 (6)0.0463 (5)
H3110.03530.13690.58490.069*
H3120.02260.01110.60810.069*
H3130.14630.01500.56690.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O160.0575 (9)0.0405 (7)0.0275 (6)0.0140 (7)0.0095 (7)0.0027 (6)
O17A0.0322 (7)0.0562 (9)0.0296 (7)0.0108 (7)0.0016 (6)0.0077 (6)
O310.0474 (8)0.0488 (8)0.0232 (6)0.0041 (7)0.0014 (6)0.0044 (6)
N170.0318 (8)0.0321 (7)0.0226 (7)0.0022 (7)0.0008 (6)0.0012 (6)
C10.0291 (9)0.0346 (9)0.0234 (8)0.0049 (8)0.0005 (7)0.0014 (7)
C20.0332 (10)0.0360 (9)0.0233 (8)0.0029 (8)0.0021 (7)0.0029 (7)
C30.0399 (10)0.0319 (9)0.0222 (8)0.0022 (8)0.0032 (8)0.0011 (7)
C40.0318 (9)0.0345 (9)0.0289 (9)0.0036 (8)0.0047 (8)0.0001 (7)
C50.0260 (9)0.0305 (8)0.0250 (8)0.0002 (8)0.0004 (7)0.0013 (7)
C60.0285 (9)0.0432 (10)0.0288 (8)0.0107 (9)0.0008 (8)0.0001 (8)
C70.0301 (9)0.0330 (9)0.0239 (8)0.0072 (8)0.0005 (7)0.0002 (7)
C80.0220 (8)0.0252 (8)0.0239 (8)0.0001 (7)0.0002 (7)0.0019 (6)
C90.0229 (8)0.0309 (8)0.0224 (8)0.0018 (7)0.0002 (7)0.0021 (6)
C100.0261 (8)0.0288 (8)0.0216 (8)0.0002 (7)0.0007 (7)0.0011 (7)
C110.0351 (10)0.0402 (10)0.0252 (8)0.0132 (9)0.0016 (8)0.0015 (8)
C120.0316 (9)0.0408 (10)0.0256 (8)0.0112 (8)0.0010 (8)0.0007 (8)
C130.0229 (8)0.0270 (8)0.0241 (8)0.0020 (7)0.0003 (7)0.0006 (7)
C140.0243 (8)0.0254 (8)0.0210 (8)0.0015 (7)0.0012 (7)0.0002 (6)
C150.0317 (10)0.0335 (9)0.0244 (8)0.0088 (8)0.0041 (8)0.0006 (7)
C160.0338 (10)0.0266 (8)0.0264 (8)0.0001 (8)0.0036 (8)0.0004 (7)
C17A0.0263 (9)0.0296 (8)0.0263 (8)0.0021 (8)0.0026 (7)0.0039 (7)
C180.0364 (10)0.0278 (9)0.0378 (10)0.0031 (8)0.0018 (9)0.0024 (7)
C190.0398 (10)0.0414 (10)0.0228 (8)0.0067 (9)0.0034 (8)0.0008 (7)
C200.0342 (9)0.0345 (9)0.0275 (9)0.0003 (8)0.0005 (8)0.0004 (7)
C210.0434 (11)0.0424 (10)0.0271 (9)0.0045 (10)0.0038 (9)0.0008 (8)
C220.0508 (12)0.0529 (12)0.0278 (9)0.0080 (11)0.0042 (9)0.0043 (9)
C310.0487 (12)0.0639 (14)0.0262 (9)0.0054 (12)0.0028 (9)0.0077 (9)
Geometric parameters (Å, º) top
O16—C161.214 (2)C11—H1120.9900
O17A—C17A1.220 (2)C12—C131.530 (2)
O31—C31.383 (2)C12—H1210.9900
O31—C311.422 (3)C12—H1220.9900
N17—C161.397 (2)C13—C17A1.522 (2)
N17—C17A1.399 (2)C13—C141.541 (2)
N17—C191.477 (2)C13—C181.545 (2)
C1—C101.385 (2)C14—C151.517 (2)
C1—C21.392 (2)C14—H141.0000
C1—H10.9500C15—C161.505 (2)
C2—C31.382 (3)C15—H1510.9900
C2—H20.9500C15—H1520.9900
C3—C41.384 (3)C18—H1810.9800
C4—C51.393 (2)C18—H1820.9800
C4—H40.9500C18—H1830.9800
C5—C101.405 (2)C19—C201.521 (2)
C5—C61.510 (2)C19—H1910.9900
C6—C71.530 (2)C19—H1920.9900
C6—H610.9900C20—C211.527 (2)
C6—H620.9900C20—H2010.9900
C7—C81.525 (2)C20—H2020.9900
C7—H710.9900C21—C221.513 (3)
C7—H720.9900C21—H2110.9900
C8—C91.533 (2)C21—H2120.9900
C8—C141.547 (2)C22—H2210.9800
C8—H81.0000C22—H2220.9800
C9—C101.525 (2)C22—H2230.9800
C9—C111.529 (2)C31—H3110.9800
C9—H91.0000C31—H3120.9800
C11—C121.529 (2)C31—H3130.9800
C11—H1110.9900
C3—O31—C31116.60 (16)C17A—C13—C14108.77 (13)
C16—N17—C17A123.99 (14)C12—C13—C14109.90 (14)
C16—N17—C19117.14 (15)C17A—C13—C18105.90 (13)
C17A—N17—C19118.78 (15)C12—C13—C18110.31 (15)
C10—C1—C2122.80 (17)C14—C13—C18113.21 (14)
C10—C1—H1118.6C15—C14—C13109.62 (13)
C2—C1—H1118.6C15—C14—C8114.41 (14)
C3—C2—C1118.42 (17)C13—C14—C8112.49 (13)
C3—C2—H2120.8C15—C14—H14106.6
C1—C2—H2120.8C13—C14—H14106.6
C2—C3—O31123.51 (17)C8—C14—H14106.6
C2—C3—C4120.11 (15)C16—C15—C14114.29 (15)
O31—C3—C4116.39 (17)C16—C15—H151108.7
C3—C4—C5121.23 (17)C14—C15—H151108.7
C3—C4—H4119.4C16—C15—H152108.7
C5—C4—H4119.4C14—C15—H152108.7
C4—C5—C10119.39 (16)H151—C15—H152107.6
C4—C5—C6119.45 (16)O16—C16—N17120.31 (16)
C10—C5—C6121.15 (15)O16—C16—C15121.63 (17)
C5—C6—C7113.45 (15)N17—C16—C15118.01 (15)
C5—C6—H61108.9O17A—C17A—N17119.96 (16)
C7—C6—H61108.9O17A—C17A—C13122.31 (16)
C5—C6—H62108.9N17—C17A—C13117.68 (14)
C7—C6—H62108.9C13—C18—H181109.5
H61—C6—H62107.7C13—C18—H182109.5
C8—C7—C6110.58 (14)H181—C18—H182109.5
C8—C7—H71109.5C13—C18—H183109.5
C6—C7—H71109.5H181—C18—H183109.5
C8—C7—H72109.5H182—C18—H183109.5
C6—C7—H72109.5N17—C19—C20113.64 (15)
H71—C7—H72108.1N17—C19—H191108.8
C7—C8—C9110.40 (14)C20—C19—H191108.8
C7—C8—C14112.85 (13)N17—C19—H192108.8
C9—C8—C14108.50 (13)C20—C19—H192108.8
C7—C8—H8108.3H191—C19—H192107.7
C9—C8—H8108.3C19—C20—C21111.44 (16)
C14—C8—H8108.3C19—C20—H201109.3
C10—C9—C11114.53 (14)C21—C20—H201109.3
C10—C9—C8114.05 (13)C19—C20—H202109.3
C11—C9—C8109.73 (14)C21—C20—H202109.3
C10—C9—H9105.9H201—C20—H202108.0
C11—C9—H9105.9C22—C21—C20113.13 (16)
C8—C9—H9105.9C22—C21—H211109.0
C1—C10—C5118.00 (15)C20—C21—H211109.0
C1—C10—C9120.52 (15)C22—C21—H212109.0
C5—C10—C9121.16 (15)C20—C21—H212109.0
C9—C11—C12110.34 (15)H211—C21—H212107.8
C9—C11—H111109.6C21—C22—H221109.5
C12—C11—H111109.6C21—C22—H222109.5
C9—C11—H112109.6H221—C22—H222109.5
C12—C11—H112109.6C21—C22—H223109.5
H111—C11—H112108.1H221—C22—H223109.5
C11—C12—C13112.93 (15)H222—C22—H223109.5
C11—C12—H121109.0O31—C31—H311109.5
C13—C12—H121109.0O31—C31—H312109.5
C11—C12—H122109.0H311—C31—H312109.5
C13—C12—H122109.0O31—C31—H313109.5
H121—C12—H122107.8H311—C31—H313109.5
C17A—C13—C12108.58 (14)H312—C31—H313109.5
C10—C1—C2—C30.7 (3)C11—C12—C13—C1873.3 (2)
C1—C2—C3—O31178.07 (17)C17A—C13—C14—C1559.07 (18)
C1—C2—C3—C41.7 (3)C12—C13—C14—C15177.82 (15)
C31—O31—C3—C213.2 (3)C18—C13—C14—C1558.35 (18)
C31—O31—C3—C4166.53 (18)C17A—C13—C14—C8172.44 (13)
C2—C3—C4—C52.6 (3)C12—C13—C14—C853.69 (18)
O31—C3—C4—C5177.14 (17)C18—C13—C14—C870.14 (18)
C3—C4—C5—C101.2 (3)C7—C8—C14—C1553.0 (2)
C3—C4—C5—C6178.21 (17)C9—C8—C14—C15175.66 (14)
C4—C5—C6—C7156.94 (17)C7—C8—C14—C13178.93 (14)
C10—C5—C6—C722.5 (3)C9—C8—C14—C1358.40 (18)
C5—C6—C7—C849.3 (2)C13—C14—C15—C1648.1 (2)
C6—C7—C8—C961.13 (19)C8—C14—C15—C16175.54 (15)
C6—C7—C8—C14177.26 (14)C17A—N17—C16—O16168.26 (17)
C7—C8—C9—C1045.21 (19)C19—N17—C16—O168.1 (2)
C14—C8—C9—C10169.36 (14)C17A—N17—C16—C1514.4 (2)
C7—C8—C9—C11175.22 (14)C19—N17—C16—C15169.19 (16)
C14—C8—C9—C1160.63 (18)C14—C15—C16—O16165.48 (17)
C2—C1—C10—C52.0 (3)C14—C15—C16—N1711.8 (2)
C2—C1—C10—C9171.44 (17)C16—N17—C17A—O17A176.58 (16)
C4—C5—C10—C11.1 (3)C19—N17—C17A—O17A0.3 (2)
C6—C5—C10—C1179.51 (16)C16—N17—C17A—C131.1 (2)
C4—C5—C10—C9172.36 (16)C19—N17—C17A—C13177.45 (15)
C6—C5—C10—C97.0 (3)C12—C13—C17A—O17A26.9 (2)
C11—C9—C10—C140.5 (2)C14—C13—C17A—O17A146.48 (17)
C8—C9—C10—C1168.08 (16)C18—C13—C17A—O17A91.55 (18)
C11—C9—C10—C5146.23 (17)C12—C13—C17A—N17155.44 (16)
C8—C9—C10—C518.6 (2)C14—C13—C17A—N1735.9 (2)
C10—C9—C11—C12170.27 (15)C18—C13—C17A—N1786.10 (18)
C8—C9—C11—C1259.98 (19)C16—N17—C19—C2081.5 (2)
C9—C11—C12—C1356.1 (2)C17A—N17—C19—C2095.0 (2)
C11—C12—C13—C17A171.04 (15)N17—C19—C20—C21179.68 (16)
C11—C12—C13—C1452.2 (2)C19—C20—C21—C22172.31 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H121···O16i0.992.593.504 (2)154
C31—H312···O16ii0.982.373.347 (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). top
Compound(I)(II)(III)(IV)(V)
(II)0.57
(III)0.250.32
(IV)0.240.230.06
(V)0.130.190.370.09
(VI)0.210.210.400.180.16
 

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