Download citation
Download citation
link to html
The buciclate ester of testosterone, C30H46O3, whose structure is reported here, was synthesized as part of a World Health Organization programme for the development of injectable contraceptive steroids.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804000820/bt6394sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804000820/bt6394Isup2.hkl
Contains datablock I

CCDC reference: 236068

Key indicators

  • Single-crystal X-ray study
  • T = 180 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.073
  • wR factor = 0.162
  • Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.770 0.960 Tmin' and Tmax expected: 0.966 0.997 RR' = 0.828 Please check that your absorption correction is appropriate. RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.124 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12 PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.83 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.04 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.65 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.26 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
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 2707 Count of symmetry unique reflns 2713 Completeness (_total/calc) 99.78% 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 9 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1994); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
C30H46O3Dx = 1.151 Mg m3
Mr = 454.67Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 4739 reflections
a = 6.2987 (13) Åθ = 3–15°
b = 10.500 (2) ŵ = 0.07 mm1
c = 39.680 (8) ÅT = 180 K
V = 2624.2 (9) Å3Plate, colourless
Z = 40.48 × 0.20 × 0.04 mm
F(000) = 1000
Data collection top
Siemens SMART
diffractometer
2707 independent reflections
Radiation source: fine-focus sealed tube1700 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.124
Detector resolution: 8.192 pixels mm-1θmax = 25.0°, θmin = 2.0°
ω scansh = 77
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 129
Tmin = 0.77, Tmax = 0.96l = 4447
12882 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0715P)2]
where P = (Fo2 + 2Fc2)/3
2707 reflections(Δ/σ)max = 0.012
298 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.21 e Å3
Special details top

Experimental. The data collection nominally covered over a hemisphere of reciprocal space, by a combination of three sets of exposures with different φ angles for the crystal; each 10 s exposure covered 0.3° in ω. The crystal-to-detector distance was 5.0 cm. Crystal decay was found to be negligible by repeating the initial frames at the end of data collection and analyzing the duplicate reflections.

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
O10.0201 (7)0.0784 (5)1.02084 (9)0.0639 (14)
O20.3125 (5)0.0327 (3)0.75502 (8)0.0357 (9)
O30.5268 (7)0.1943 (4)0.74176 (9)0.0580 (13)
C10.1796 (8)0.1667 (6)0.93768 (12)0.0431 (17)
H1A0.24530.24190.92680.052*
H1B0.28930.09940.93920.052*
C20.1124 (10)0.2028 (7)0.97275 (12)0.058 (2)
H2A0.01170.27500.97160.069*
H2B0.23820.23070.98570.069*
C30.0085 (9)0.0925 (6)0.99055 (13)0.0424 (15)
C40.1254 (9)0.0123 (6)0.96882 (12)0.0381 (15)
H4A0.20750.05270.97920.046*
C50.1384 (8)0.0253 (5)0.93561 (12)0.0306 (13)
C60.2954 (9)0.0519 (6)0.91553 (12)0.0400 (15)
H6A0.35990.11700.93040.048*
H6B0.41040.00480.90750.048*
C70.1947 (8)0.1178 (5)0.88532 (12)0.0342 (14)
H7A0.30690.15990.87180.041*
H7B0.09570.18450.89330.041*
C80.0750 (7)0.0241 (5)0.86319 (10)0.0257 (12)
H8A0.17840.03880.85380.031*
C90.0913 (7)0.0480 (5)0.88427 (11)0.0262 (12)
H9A0.18960.01820.89340.031*
C100.0017 (8)0.1189 (5)0.91541 (11)0.0300 (13)
C110.2288 (8)0.1358 (5)0.86198 (11)0.0310 (14)
H11A0.34420.17240.87590.037*
H11B0.14010.20720.85380.037*
C120.3261 (8)0.0677 (5)0.83186 (11)0.0333 (14)
H12A0.40090.13050.81750.040*
H12B0.43200.00500.83990.040*
C130.1584 (7)0.0005 (5)0.81099 (11)0.0256 (12)
C140.0345 (8)0.0912 (5)0.83422 (10)0.0267 (12)
H14A0.14290.14840.84470.032*
C150.0890 (9)0.1735 (6)0.80980 (12)0.0441 (16)
H15A0.11890.25800.81980.053*
H15B0.22530.13250.80370.053*
C160.0548 (9)0.1869 (6)0.77847 (11)0.0379 (15)
H16A0.02230.16160.75780.045*
H16B0.10490.27570.77590.045*
C170.2419 (8)0.0966 (5)0.78522 (11)0.0293 (13)
H17A0.36250.14560.79520.035*
C180.1431 (10)0.2323 (6)0.90492 (13)0.0479 (16)
H18A0.19800.27480.92510.072*
H18B0.05910.29290.89170.072*
H18C0.26210.20130.89130.072*
C190.0159 (9)0.0976 (5)0.79310 (11)0.0364 (14)
H19A0.10360.15310.77900.055*
H19B0.08800.05300.77900.055*
H19C0.05870.14900.81000.055*
C200.4528 (8)0.0909 (6)0.73494 (12)0.0334 (14)
C210.4912 (8)0.0180 (6)0.70394 (11)0.0333 (14)
H21A0.46460.07400.70900.040*
C220.7217 (8)0.0311 (6)0.69120 (12)0.0376 (15)
H22A0.75410.12200.68700.045*
H22B0.82090.00060.70860.045*
C230.7526 (8)0.0444 (6)0.65881 (11)0.0386 (15)
H23A0.89880.02950.65050.046*
H23B0.73970.13620.66410.046*
C240.5987 (7)0.0129 (5)0.63068 (11)0.0271 (13)
H24A0.62740.07710.62380.033*
C250.3724 (8)0.0172 (6)0.64396 (12)0.0419 (16)
H25A0.27570.01670.62650.050*
H25B0.33270.10710.64810.050*
C260.3406 (8)0.0582 (6)0.67629 (12)0.0430 (16)
H26A0.36160.14980.67150.052*
H26B0.19270.04660.68420.052*
C270.6252 (8)0.0945 (6)0.59955 (11)0.0328 (13)
H27A0.50560.07630.58410.039*
H27B0.61370.18490.60640.039*
C280.8307 (8)0.0778 (6)0.58009 (12)0.0396 (15)
H28A0.84170.01160.57240.047*
H28B0.95190.09480.59530.047*
C290.8452 (10)0.1655 (6)0.54983 (12)0.0444 (16)
H29A0.72060.15090.53510.053*
H29B0.83980.25490.55770.053*
C301.0482 (10)0.1460 (7)0.52910 (13)0.068 (2)
H30A1.04890.20520.51000.101*
H30B1.17250.16200.54340.101*
H30C1.05290.05830.52070.101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.075 (3)0.077 (4)0.041 (2)0.015 (3)0.008 (2)0.003 (2)
O20.039 (2)0.032 (2)0.0360 (19)0.0046 (19)0.0089 (17)0.0038 (18)
O30.066 (3)0.047 (3)0.060 (2)0.025 (3)0.027 (2)0.016 (2)
C10.025 (3)0.061 (5)0.043 (3)0.013 (3)0.009 (3)0.016 (3)
C20.044 (4)0.082 (6)0.047 (4)0.014 (4)0.001 (3)0.019 (4)
C30.043 (3)0.053 (4)0.031 (3)0.019 (4)0.000 (3)0.002 (3)
C40.042 (3)0.042 (4)0.031 (3)0.002 (3)0.008 (3)0.002 (3)
C50.021 (3)0.028 (4)0.043 (3)0.001 (3)0.003 (2)0.005 (3)
C60.030 (3)0.047 (4)0.043 (3)0.015 (3)0.009 (3)0.001 (3)
C70.027 (3)0.035 (4)0.041 (3)0.014 (3)0.001 (2)0.001 (3)
C80.022 (3)0.024 (3)0.031 (3)0.005 (2)0.003 (2)0.003 (2)
C90.022 (3)0.020 (3)0.037 (3)0.001 (2)0.002 (2)0.003 (2)
C100.027 (3)0.026 (3)0.037 (3)0.002 (3)0.000 (2)0.002 (2)
C110.029 (3)0.037 (4)0.027 (3)0.008 (3)0.001 (2)0.002 (2)
C120.031 (3)0.028 (4)0.041 (3)0.005 (3)0.003 (2)0.002 (3)
C130.026 (3)0.020 (3)0.031 (3)0.001 (2)0.000 (2)0.000 (2)
C140.029 (3)0.022 (3)0.029 (3)0.001 (3)0.003 (2)0.001 (2)
C150.045 (4)0.043 (4)0.045 (3)0.010 (3)0.006 (3)0.003 (3)
C160.049 (4)0.031 (4)0.035 (3)0.002 (3)0.001 (3)0.002 (3)
C170.033 (3)0.032 (3)0.023 (3)0.003 (3)0.002 (2)0.004 (2)
C180.050 (4)0.038 (4)0.056 (3)0.004 (3)0.015 (3)0.001 (3)
C190.038 (3)0.032 (4)0.039 (3)0.007 (3)0.001 (2)0.005 (3)
C200.033 (3)0.030 (4)0.036 (3)0.001 (3)0.005 (3)0.004 (3)
C210.033 (3)0.039 (4)0.028 (3)0.010 (3)0.005 (2)0.000 (2)
C220.020 (3)0.054 (4)0.040 (3)0.001 (3)0.003 (2)0.007 (3)
C230.022 (3)0.054 (4)0.039 (3)0.002 (3)0.001 (2)0.006 (3)
C240.020 (3)0.030 (4)0.031 (3)0.010 (2)0.002 (2)0.000 (2)
C250.020 (3)0.057 (5)0.049 (3)0.003 (3)0.001 (3)0.010 (3)
C260.015 (3)0.056 (4)0.058 (4)0.001 (3)0.003 (3)0.015 (3)
C270.026 (3)0.034 (4)0.039 (3)0.005 (3)0.001 (2)0.005 (3)
C280.033 (3)0.042 (4)0.044 (3)0.005 (3)0.002 (3)0.006 (3)
C290.049 (4)0.048 (4)0.036 (3)0.002 (3)0.005 (3)0.008 (3)
C300.053 (4)0.092 (6)0.059 (4)0.013 (4)0.015 (3)0.014 (4)
Geometric parameters (Å, º) top
O1—C31.213 (5)C15—H15B0.9900
O2—C201.338 (6)C16—C171.536 (7)
O2—C171.443 (5)C16—H16A0.9900
O3—C201.212 (6)C16—H16B0.9900
C1—C21.503 (7)C17—H17A1.0000
C1—C101.529 (7)C18—H18A0.9800
C1—H1A0.9900C18—H18B0.9800
C1—H1B0.9900C18—H18C0.9800
C2—C31.506 (8)C19—H19A0.9800
C2—H2A0.9900C19—H19B0.9800
C2—H2B0.9900C19—H19C0.9800
C3—C41.471 (8)C20—C211.469 (7)
C4—C51.328 (6)C21—C261.510 (7)
C4—H4A0.9500C21—C221.544 (7)
C5—C61.507 (7)C21—H21A1.0000
C5—C101.533 (7)C22—C231.523 (7)
C6—C71.522 (7)C22—H22A0.9900
C6—H6A0.9900C22—H22B0.9900
C6—H6B0.9900C23—C241.515 (7)
C7—C81.519 (6)C23—H23A0.9900
C7—H7A0.9900C23—H23B0.9900
C7—H7B0.9900C24—C271.512 (6)
C8—C141.514 (6)C24—C251.520 (7)
C8—C91.540 (6)C24—H24A1.0000
C8—H8A1.0000C25—C261.521 (7)
C9—C111.543 (6)C25—H25A0.9900
C9—C101.557 (7)C25—H25B0.9900
C9—H9A1.0000C26—H26A0.9900
C10—C181.544 (8)C26—H26B0.9900
C11—C121.522 (6)C27—C281.517 (7)
C11—H11A0.9900C27—H27A0.9900
C11—H11B0.9900C27—H27B0.9900
C12—C131.521 (6)C28—C291.516 (7)
C12—H12A0.9900C28—H28A0.9900
C12—H12B0.9900C28—H28B0.9900
C13—C171.530 (7)C29—C301.534 (8)
C13—C141.538 (6)C29—H29A0.9900
C13—C191.539 (7)C29—H29B0.9900
C14—C151.513 (6)C30—H30A0.9800
C14—H14A1.0000C30—H30B0.9800
C15—C161.545 (7)C30—H30C0.9800
C15—H15A0.9900
C20—O2—C17119.1 (4)C17—C16—H16B110.8
C2—C1—C10114.0 (5)C15—C16—H16B110.8
C2—C1—H1A108.7H16A—C16—H16B108.9
C10—C1—H1A108.7O2—C17—C13110.8 (4)
C2—C1—H1B108.7O2—C17—C16112.2 (4)
C10—C1—H1B108.7C13—C17—C16105.1 (4)
H1A—C1—H1B107.6O2—C17—H17A109.6
C3—C2—C1111.3 (6)C13—C17—H17A109.6
C3—C2—H2A109.4C16—C17—H17A109.6
C1—C2—H2A109.4C10—C18—H18A109.5
C3—C2—H2B109.4C10—C18—H18B109.5
C1—C2—H2B109.4H18A—C18—H18B109.5
H2A—C2—H2B108.0C10—C18—H18C109.5
O1—C3—C4123.0 (6)H18A—C18—H18C109.5
O1—C3—C2122.2 (6)H18B—C18—H18C109.5
C4—C3—C2114.5 (4)C13—C19—H19A109.5
C5—C4—C3123.9 (5)C13—C19—H19B109.5
C5—C4—H4A118.0H19A—C19—H19B109.5
C3—C4—H4A118.0C13—C19—H19C109.5
C4—C5—C6120.7 (5)H19A—C19—H19C109.5
C4—C5—C10123.4 (5)H19B—C19—H19C109.5
C6—C5—C10115.9 (4)O3—C20—O2122.0 (5)
C5—C6—C7112.8 (4)O3—C20—C21126.2 (5)
C5—C6—H6A109.0O2—C20—C21111.7 (5)
C7—C6—H6A109.0C20—C21—C26111.0 (4)
C5—C6—H6B109.0C20—C21—C22112.5 (4)
C7—C6—H6B109.0C26—C21—C22109.1 (4)
H6A—C6—H6B107.8C20—C21—H21A108.0
C8—C7—C6111.6 (5)C26—C21—H21A108.0
C8—C7—H7A109.3C22—C21—H21A108.0
C6—C7—H7A109.3C23—C22—C21110.5 (4)
C8—C7—H7B109.3C23—C22—H22A109.5
C6—C7—H7B109.3C21—C22—H22A109.6
H7A—C7—H7B108.0C23—C22—H22B109.5
C14—C8—C7111.3 (4)C21—C22—H22B109.6
C14—C8—C9109.4 (4)H22A—C22—H22B108.1
C7—C8—C9110.0 (3)C24—C23—C22115.2 (4)
C14—C8—H8A108.7C24—C23—H23A108.5
C7—C8—H8A108.7C22—C23—H23A108.5
C9—C8—H8A108.7C24—C23—H23B108.5
C8—C9—C11111.4 (3)C22—C23—H23B108.5
C8—C9—C10114.2 (4)H23A—C23—H23B107.5
C11—C9—C10112.4 (4)C27—C24—C23114.0 (4)
C8—C9—H9A106.1C27—C24—C25111.7 (4)
C11—C9—H9A106.1C23—C24—C25109.8 (4)
C10—C9—H9A106.1C27—C24—H24A107.0
C1—C10—C5109.1 (4)C23—C24—H24A107.0
C1—C10—C18109.5 (5)C25—C24—H24A107.0
C5—C10—C18108.2 (4)C26—C25—C24113.6 (4)
C1—C10—C9109.5 (4)C26—C25—H25A108.8
C5—C10—C9108.7 (4)C24—C25—H25A108.8
C18—C10—C9111.8 (4)C26—C25—H25B108.8
C12—C11—C9113.3 (4)C24—C25—H25B108.8
C12—C11—H11A108.9H25A—C25—H25B107.7
C9—C11—H11A108.9C21—C26—C25112.6 (5)
C12—C11—H11B108.9C21—C26—H26A109.1
C9—C11—H11B108.9C25—C26—H26A109.1
H11A—C11—H11B107.7C21—C26—H26B109.1
C11—C12—C13111.6 (4)C25—C26—H26B109.1
C11—C12—H12A109.3H26A—C26—H26B107.8
C13—C12—H12A109.3C24—C27—C28116.4 (4)
C11—C12—H12B109.3C24—C27—H27A108.2
C13—C12—H12B109.3C28—C27—H27A108.2
H12A—C12—H12B108.0C24—C27—H27B108.2
C12—C13—C17115.8 (4)C28—C27—H27B108.2
C12—C13—C14108.5 (4)H27A—C27—H27B107.3
C17—C13—C1499.6 (4)C29—C28—C27112.6 (5)
C12—C13—C19110.0 (4)C29—C28—H28A109.1
C17—C13—C19109.5 (4)C27—C28—H28A109.1
C14—C13—C19113.2 (4)C29—C28—H28B109.1
C15—C14—C8121.2 (4)C27—C28—H28B109.1
C15—C14—C13103.3 (3)H28A—C28—H28B107.8
C8—C14—C13113.4 (4)C28—C29—C30113.2 (5)
C15—C14—H14A105.9C28—C29—H29A108.9
C8—C14—H14A105.9C30—C29—H29A108.9
C13—C14—H14A105.9C28—C29—H29B108.9
C14—C15—C16105.4 (4)C30—C29—H29B108.9
C14—C15—H15A110.7H29A—C29—H29B107.8
C16—C15—H15A110.7C29—C30—H30A109.5
C14—C15—H15B110.7C29—C30—H30B109.5
C16—C15—H15B110.7H30A—C30—H30B109.5
H15A—C15—H15B108.8C29—C30—H30C109.5
C17—C16—C15104.7 (4)H30A—C30—H30C109.5
C17—C16—H16A110.8H30B—C30—H30C109.5
C15—C16—H16A110.8
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds