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In the title mol­ecule, C24H44N2, also known as pachys­amine A, all four rings are trans fused. The cylo­hexane rings adopt chair conformations and the cyclo­pentane ring a half-chair form. The methyl­amino and di­methyl­amino­ethyl substituents are equatorially attached. The crystal structure is stabilized by van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021810/ci6279sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021810/ci6279Isup2.hkl
Contains datablock I

CCDC reference: 226967

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.058
  • wR factor = 0.159
  • Data-to-parameter ratio = 11.6

checkCIF/PLATON results

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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.59 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.22 Ratio PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... N2 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1 ... ?
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 27.48 From the CIF: _reflns_number_total 2766 Count of symmetry unique reflns 2780 Completeness (_total/calc) 99.50% 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 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

[17-(1-Dimethylamino-ethyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a] phenanthren-3-yl]-methyl-amine top
Crystal data top
C24H44N2F(000) = 404
Mr = 360.61Dx = 1.079 Mg m3
Monoclinic, P21Melting point: 444-447 K K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 12.664 (3) ÅCell parameters from 2500 reflections
b = 6.4003 (15) Åθ = 1.5–27.5°
c = 13.801 (3) ŵ = 0.06 mm1
β = 97.015 (5)°T = 293 K
V = 1110.2 (4) Å3Block, colourless
Z = 20.54 × 0.35 × 0.18 mm
Data collection top
Siemmens SMART CCD area-detector
diffractometer
2766 independent reflections
Radiation source: fine-focus sealed tube2192 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
Detector resolution: 8.33 pixels mm-1θmax = 27.5°, θmin = 1.5°
ω scansh = 1611
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 88
Tmin = 0.967, Tmax = 0.989l = 1717
7516 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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0963P)2 + 0.0365P]
where P = (Fo2 + 2Fc2)/3
2766 reflections(Δ/σ)max = 0.001
238 parametersΔρmax = 0.22 e Å3
1 restraintΔρmin = 0.19 e Å3
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
xyzUiso*/Ueq
N10.9730 (2)0.5665 (5)0.55509 (17)0.0729 (7)
H10.958 (3)0.675 (7)0.521 (2)0.087 (12)*
N20.18598 (19)0.1242 (5)0.92921 (18)0.0780 (8)
C10.6839 (2)0.4974 (4)0.59824 (18)0.0565 (6)
H1A0.62020.50150.55160.068*
H1B0.67710.60420.64700.068*
C20.7792 (2)0.5484 (4)0.54564 (17)0.0620 (7)
H2A0.78090.45240.49150.074*
H2B0.77110.68860.51910.074*
C30.8834 (2)0.5346 (5)0.61124 (17)0.0603 (7)
H30.88480.64550.66030.072*
C40.8932 (2)0.3281 (5)0.66320 (18)0.0637 (7)
H4A0.95680.32880.71010.076*
H4B0.90080.21820.61620.076*
C50.79699 (19)0.2810 (5)0.71627 (16)0.0543 (6)
H50.79270.39460.76330.065*
C60.8123 (2)0.0809 (6)0.7756 (2)0.0752 (9)
H6A0.81730.03640.73180.090*
H6B0.87850.08900.81890.090*
C70.7211 (2)0.0446 (6)0.83532 (19)0.0731 (9)
H7A0.73040.08990.86760.088*
H7B0.72260.15140.88530.088*
C80.61413 (19)0.0494 (4)0.77268 (16)0.0510 (6)
H80.61070.06900.72730.061*
C90.60032 (18)0.2527 (4)0.71252 (15)0.0457 (5)
H90.60670.36760.75980.055*
C100.6912 (2)0.2830 (4)0.64841 (14)0.0478 (5)
C110.4885 (2)0.2677 (5)0.65746 (17)0.0586 (6)
H11A0.47960.40490.62770.070*
H11B0.48170.16520.60530.070*
C120.3998 (2)0.2326 (4)0.72083 (19)0.0562 (6)
H12A0.33180.23360.67990.067*
H12B0.39970.34630.76730.067*
C130.41254 (18)0.0262 (4)0.77598 (15)0.0474 (5)
C140.52355 (18)0.0293 (4)0.83415 (14)0.0501 (6)
H140.52630.15460.87520.060*
C150.5230 (2)0.1557 (6)0.90295 (19)0.0699 (8)
H15A0.57310.13490.96120.084*
H15B0.54080.28400.87120.084*
C160.4088 (2)0.1621 (6)0.92793 (19)0.0707 (8)
H16A0.40690.12450.99580.085*
H16B0.37950.30150.91750.085*
C170.34384 (19)0.0044 (4)0.86039 (15)0.0531 (6)
H170.34420.12840.89580.064*
C180.3974 (2)0.1580 (5)0.70505 (19)0.0641 (7)
H18A0.45040.15240.66100.096*
H18B0.32790.15060.66860.096*
H18C0.40430.28660.74110.096*
C190.6865 (3)0.1130 (5)0.57007 (18)0.0660 (7)
H19A0.74890.12090.53720.099*
H19B0.62440.13330.52370.099*
H19C0.68310.02170.60010.099*
C200.2285 (2)0.0729 (5)0.83816 (18)0.0623 (7)
H200.22900.20330.80100.075*
C210.1607 (2)0.0809 (7)0.7739 (2)0.0883 (11)
H21A0.08750.03870.76870.133*
H21B0.18360.08330.71010.133*
H21C0.16820.21790.80230.133*
C220.1661 (3)0.0548 (10)0.9872 (3)0.1177 (17)
H22A0.14370.00941.04770.177*
H22B0.11130.13890.95230.177*
H22C0.23010.13581.00020.177*
C230.0962 (3)0.2612 (9)0.9149 (3)0.1112 (15)
H23A0.07050.28720.97640.167*
H23B0.11690.39090.88770.167*
H23C0.04090.19750.87090.167*
C241.0740 (3)0.5889 (8)0.6138 (2)0.0938 (12)
H24A1.12440.64880.57520.141*
H24B1.09890.45420.63730.141*
H24C1.06640.67860.66830.141*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0857 (17)0.0774 (19)0.0582 (13)0.0115 (15)0.0189 (12)0.0103 (14)
N20.0628 (13)0.101 (2)0.0707 (13)0.0016 (15)0.0124 (11)0.0068 (16)
C10.0730 (16)0.0430 (13)0.0543 (12)0.0098 (12)0.0112 (11)0.0103 (11)
C20.0873 (18)0.0454 (14)0.0555 (12)0.0041 (13)0.0179 (13)0.0106 (11)
C30.0799 (17)0.0563 (15)0.0475 (11)0.0047 (14)0.0190 (11)0.0024 (12)
C40.0637 (14)0.074 (2)0.0550 (12)0.0060 (14)0.0153 (11)0.0108 (14)
C50.0594 (13)0.0587 (15)0.0460 (10)0.0083 (12)0.0107 (10)0.0080 (12)
C60.0605 (15)0.095 (2)0.0716 (15)0.0204 (16)0.0157 (13)0.0376 (17)
C70.0578 (14)0.096 (2)0.0662 (14)0.0157 (15)0.0099 (12)0.0396 (17)
C80.0586 (13)0.0504 (14)0.0445 (10)0.0124 (11)0.0083 (9)0.0118 (10)
C90.0578 (13)0.0376 (11)0.0412 (10)0.0072 (10)0.0047 (9)0.0006 (9)
C100.0659 (13)0.0378 (12)0.0410 (10)0.0080 (10)0.0110 (10)0.0021 (10)
C110.0681 (15)0.0523 (14)0.0537 (12)0.0096 (13)0.0007 (11)0.0139 (12)
C120.0575 (14)0.0469 (15)0.0622 (13)0.0099 (12)0.0005 (11)0.0086 (11)
C130.0582 (12)0.0397 (12)0.0436 (10)0.0074 (11)0.0032 (9)0.0021 (10)
C140.0556 (12)0.0515 (14)0.0425 (10)0.0076 (12)0.0038 (9)0.0061 (11)
C150.0642 (15)0.086 (2)0.0599 (13)0.0104 (16)0.0085 (12)0.0306 (16)
C160.0617 (15)0.089 (2)0.0610 (14)0.0027 (16)0.0061 (12)0.0228 (16)
C170.0602 (14)0.0509 (14)0.0476 (11)0.0034 (12)0.0040 (10)0.0034 (11)
C180.0845 (18)0.0518 (15)0.0577 (13)0.0062 (14)0.0152 (13)0.0080 (12)
C190.094 (2)0.0513 (15)0.0565 (13)0.0016 (15)0.0246 (13)0.0075 (12)
C200.0589 (14)0.0659 (17)0.0612 (13)0.0019 (13)0.0036 (12)0.0006 (13)
C210.0638 (17)0.104 (3)0.0948 (19)0.0047 (19)0.0009 (16)0.022 (2)
C220.099 (3)0.164 (5)0.099 (2)0.001 (3)0.047 (2)0.027 (3)
C230.078 (2)0.144 (4)0.113 (3)0.025 (3)0.019 (2)0.025 (3)
C240.086 (2)0.119 (3)0.0795 (18)0.033 (2)0.0202 (17)0.010 (2)
Geometric parameters (Å, º) top
N1—C241.436 (4)C12—C131.523 (3)
N1—C31.465 (3)C12—H12A0.97
N1—H10.84 (4)C12—H12B0.97
N2—C231.430 (5)C13—C181.529 (3)
N2—C221.437 (6)C13—C141.531 (3)
N2—C201.464 (4)C13—C171.549 (3)
C1—C21.518 (4)C14—C151.519 (4)
C1—C101.534 (3)C14—H140.98
C1—H1A0.97C15—C161.528 (4)
C1—H1B0.97C15—H15A0.97
C2—C31.508 (4)C15—H15B0.97
C2—H2A0.97C16—C171.542 (4)
C2—H2B0.97C16—H16A0.97
C3—C41.501 (4)C16—H16B0.97
C3—H30.98C17—C201.520 (4)
C4—C51.526 (3)C17—H170.98
C4—H4A0.97C18—H18A0.96
C4—H4B0.97C18—H18B0.96
C5—C61.519 (4)C18—H18C0.96
C5—C101.538 (3)C19—H19A0.96
C5—H50.98C19—H19B0.96
C6—C71.517 (4)C19—H19C0.96
C6—H6A0.97C20—C211.519 (4)
C6—H6B0.97C20—H200.98
C7—C81.516 (3)C21—H21A0.96
C7—H7A0.97C21—H21B0.96
C7—H7B0.97C21—H21C0.96
C8—C141.513 (3)C22—H22A0.96
C8—C91.542 (3)C22—H22B0.96
C8—H80.98C22—H22C0.96
C9—C111.526 (3)C23—H23A0.96
C9—C101.547 (3)C23—H23B0.96
C9—H90.98C23—H23C0.96
C10—C191.530 (3)C24—H24A0.96
C11—C121.523 (4)C24—H24B0.96
C11—H11A0.97C24—H24C0.96
C11—H11B0.97
C24—N1—C3114.2 (2)C11—C12—H12B109.2
C24—N1—H1111 (3)C13—C12—H12B109.2
C3—N1—H1106 (2)H12A—C12—H12B107.9
C23—N2—C22112.1 (3)C12—C13—C18110.56 (18)
C23—N2—C20112.9 (3)C12—C13—C14106.6 (2)
C22—N2—C20114.0 (3)C18—C13—C14112.4 (2)
C2—C1—C10113.6 (2)C12—C13—C17116.8 (2)
C2—C1—H1A108.8C18—C13—C17110.2 (2)
C10—C1—H1A108.8C14—C13—C1799.87 (16)
C2—C1—H1B108.8C8—C14—C15118.6 (2)
C10—C1—H1B108.8C8—C14—C13114.68 (16)
H1A—C1—H1B107.7C15—C14—C13104.1 (2)
C3—C2—C1112.85 (19)C8—C14—H14106.2
C3—C2—H2A109.0C15—C14—H14106.2
C1—C2—H2A109.0C13—C14—H14106.2
C3—C2—H2B109.0C14—C15—C16103.8 (2)
C1—C2—H2B109.0C14—C15—H15A111.0
H2A—C2—H2B107.8C16—C15—H15A111.0
N1—C3—C4110.6 (2)C14—C15—H15B111.0
N1—C3—C2110.58 (19)C16—C15—H15B111.0
C4—C3—C2110.7 (2)H15A—C15—H15B109.0
N1—C3—H3108.3C15—C16—C17107.2 (2)
C4—C3—H3108.3C15—C16—H16A110.3
C2—C3—H3108.3C17—C16—H16A110.3
C3—C4—C5112.3 (2)C15—C16—H16B110.3
C3—C4—H4A109.2C17—C16—H16B110.3
C5—C4—H4A109.2H16A—C16—H16B108.5
C3—C4—H4B109.2C20—C17—C16111.2 (2)
C5—C4—H4B109.2C20—C17—C13119.92 (19)
H4A—C4—H4B107.9C16—C17—C13103.30 (19)
C6—C5—C4111.6 (2)C20—C17—H17107.3
C6—C5—C10112.3 (2)C16—C17—H17107.3
C4—C5—C10113.16 (18)C13—C17—H17107.3
C6—C5—H5106.4C13—C18—H18A109.5
C4—C5—H5106.4C13—C18—H18B109.5
C10—C5—H5106.4H18A—C18—H18B109.5
C7—C6—C5111.5 (2)C13—C18—H18C109.5
C7—C6—H6A109.3H18A—C18—H18C109.5
C5—C6—H6A109.3H18B—C18—H18C109.5
C7—C6—H6B109.3C10—C19—H19A109.5
C5—C6—H6B109.3C10—C19—H19B109.5
H6A—C6—H6B108.0H19A—C19—H19B109.5
C8—C7—C6111.9 (2)C10—C19—H19C109.5
C8—C7—H7A109.2H19A—C19—H19C109.5
C6—C7—H7A109.2H19B—C19—H19C109.5
C8—C7—H7B109.2N2—C20—C21113.9 (2)
C6—C7—H7B109.2N2—C20—C17109.7 (2)
H7A—C7—H7B107.9C21—C20—C17113.1 (3)
C14—C8—C7111.39 (17)N2—C20—H20106.5
C14—C8—C9109.23 (19)C21—C20—H20106.5
C7—C8—C9111.0 (2)C17—C20—H20106.5
C14—C8—H8108.4C20—C21—H21A109.5
C7—C8—H8108.4C20—C21—H21B109.5
C9—C8—H8108.4H21A—C21—H21B109.5
C11—C9—C8111.0 (2)C20—C21—H21C109.5
C11—C9—C10114.63 (17)H21A—C21—H21C109.5
C8—C9—C10111.74 (18)H21B—C21—H21C109.5
C11—C9—H9106.3N2—C22—H22A109.5
C8—C9—H9106.3N2—C22—H22B109.5
C10—C9—H9106.3H22A—C22—H22B109.5
C19—C10—C1108.78 (18)N2—C22—H22C109.5
C19—C10—C5112.3 (2)H22A—C22—H22C109.5
C1—C10—C5106.4 (2)H22B—C22—H22C109.5
C19—C10—C9110.3 (2)N2—C23—H23A109.5
C1—C10—C9111.27 (19)N2—C23—H23B109.5
C5—C10—C9107.72 (16)H23A—C23—H23B109.5
C12—C11—C9114.19 (18)N2—C23—H23C109.5
C12—C11—H11A108.7H23A—C23—H23C109.5
C9—C11—H11A108.7H23B—C23—H23C109.5
C12—C11—H11B108.7N1—C24—H24A109.5
C9—C11—H11B108.7N1—C24—H24B109.5
H11A—C11—H11B107.6H24A—C24—H24B109.5
C11—C12—C13112.0 (2)N1—C24—H24C109.5
C11—C12—H12A109.2H24A—C24—H24C109.5
C13—C12—H12A109.2H24B—C24—H24C109.5
C10—C1—C2—C355.5 (3)C10—C9—C11—C12178.6 (2)
C24—N1—C3—C466.4 (4)C9—C11—C12—C1354.4 (3)
C24—N1—C3—C2170.6 (3)C11—C12—C13—C1866.8 (3)
C1—C2—C3—N1174.9 (2)C11—C12—C13—C1455.6 (2)
C1—C2—C3—C452.0 (3)C11—C12—C13—C17166.1 (2)
N1—C3—C4—C5175.6 (2)C7—C8—C14—C1554.5 (3)
C2—C3—C4—C552.7 (3)C9—C8—C14—C15177.5 (2)
C3—C4—C5—C6175.1 (2)C7—C8—C14—C13178.2 (2)
C3—C4—C5—C1057.1 (3)C9—C8—C14—C1358.7 (3)
C4—C5—C6—C7174.9 (3)C12—C13—C14—C860.3 (3)
C10—C5—C6—C756.8 (3)C18—C13—C14—C860.9 (3)
C5—C6—C7—C854.0 (4)C17—C13—C14—C8177.8 (2)
C6—C7—C8—C14175.7 (3)C12—C13—C14—C15168.5 (2)
C6—C7—C8—C953.7 (3)C18—C13—C14—C1570.2 (2)
C14—C8—C9—C1151.0 (2)C17—C13—C14—C1546.6 (2)
C7—C8—C9—C11174.2 (2)C8—C14—C15—C16163.6 (2)
C14—C8—C9—C10179.63 (19)C13—C14—C15—C1634.7 (3)
C7—C8—C9—C1056.4 (2)C14—C15—C16—C178.9 (3)
C2—C1—C10—C1966.2 (3)C15—C16—C17—C20149.6 (3)
C2—C1—C10—C555.0 (2)C15—C16—C17—C1319.7 (3)
C2—C1—C10—C9172.0 (2)C12—C13—C17—C2081.4 (3)
C6—C5—C10—C1964.3 (3)C18—C13—C17—C2045.8 (3)
C4—C5—C10—C1963.2 (3)C14—C13—C17—C20164.3 (2)
C6—C5—C10—C1176.8 (2)C12—C13—C17—C16154.2 (2)
C4—C5—C10—C155.7 (3)C18—C13—C17—C1678.5 (3)
C6—C5—C10—C957.4 (3)C14—C13—C17—C1639.9 (2)
C4—C5—C10—C9175.1 (2)C23—N2—C20—C2174.6 (4)
C11—C9—C10—C1961.6 (3)C22—N2—C20—C2154.8 (4)
C8—C9—C10—C1965.8 (2)C23—N2—C20—C17157.6 (3)
C11—C9—C10—C159.3 (3)C22—N2—C20—C1773.1 (3)
C8—C9—C10—C1173.31 (19)C16—C17—C20—N250.2 (3)
C11—C9—C10—C5175.5 (2)C13—C17—C20—N2170.7 (2)
C8—C9—C10—C557.1 (2)C16—C17—C20—C21178.5 (2)
C8—C9—C11—C1250.9 (3)C13—C17—C20—C2161.0 (3)
 

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