Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804011535/su6104sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804011535/su6104Isup2.hkl |
CCDC reference: 242363
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.004 Å
- R factor = 0.034
- wR factor = 0.065
- Data-to-parameter ratio = 10.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT049_ALERT_1_B Calculated Density less than 1.0 gcm-3 ......... 1.00
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 42 Perc. PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C31
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 25.31 From the CIF: _reflns_number_total 2101 Count of symmetry unique reflns 2118 Completeness (_total/calc) 99.20% 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 1 ALERT level B = Potentially serious problem 2 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 1 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
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).
C21H39N | F(000) = 688 |
Mr = 305.53 | Dx = 0.999 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 10616 reflections |
a = 11.050 (3) Å | θ = 3.1–25.3° |
b = 11.2116 (4) Å | µ = 0.06 mm−1 |
c = 16.3949 (6) Å | T = 291 K |
V = 2031.2 (6) Å3 | Block, colourless |
Z = 4 | 0.12 × 0.12 × 0.08 mm |
Nonius KappaCCD diffractometer | 882 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.037 |
Graphite monochromator | θmax = 25.3°, θmin = 3.1° |
Detector resolution: 19 vertical, 18 horizontal pixels mm-1 | h = −13→13 |
197 frames via ω–rotation (Δω=1°) and two times 30 s per frame (two sets at different κ–angles) scans | k = −13→13 |
2101 measured reflections | l = −19→19 |
2101 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.034 | w = 1/[σ2(Fo2) + (0.0162P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.065 | (Δ/σ)max < 0.001 |
S = 0.88 | Δρmax = 0.08 e Å−3 |
2101 reflections | Δρmin = −0.08 e Å−3 |
200 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0226 (10) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map |
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 | ||
N1 | 0.2752 (2) | 0.55534 (19) | 0.14983 (12) | 0.0657 (6) | |
C11 | 0.4071 (3) | 0.3807 (3) | 0.11635 (16) | 0.0732 (8) | |
H11A | 0.4270 | 0.4229 | 0.0657 | 0.088* | |
C12 | 0.3065 (3) | 0.2948 (3) | 0.09758 (18) | 0.0884 (9) | |
H12A | 0.2381 | 0.3388 | 0.0759 | 0.106* | |
H12B | 0.2807 | 0.2568 | 0.1478 | 0.106* | |
C13 | 0.3428 (3) | 0.1995 (3) | 0.03696 (18) | 0.1056 (11) | |
H13A | 0.2763 | 0.1440 | 0.0297 | 0.127* | |
H13B | 0.3596 | 0.2362 | −0.0154 | 0.127* | |
C14 | 0.4526 (4) | 0.1328 (3) | 0.0653 (2) | 0.1154 (12) | |
H14A | 0.4769 | 0.0760 | 0.0238 | 0.139* | |
H14B | 0.4332 | 0.0887 | 0.1145 | 0.139* | |
C15 | 0.5558 (3) | 0.2176 (3) | 0.0823 (2) | 0.1187 (13) | |
H15A | 0.5810 | 0.2550 | 0.0317 | 0.142* | |
H15B | 0.6241 | 0.1731 | 0.1037 | 0.142* | |
C16 | 0.5199 (3) | 0.3146 (3) | 0.14374 (18) | 0.0974 (11) | |
H16A | 0.5053 | 0.2783 | 0.1965 | 0.117* | |
H16B | 0.5861 | 0.3708 | 0.1497 | 0.117* | |
C17 | 0.3695 (3) | 0.4736 (3) | 0.17903 (15) | 0.0790 (9) | |
H17A | 0.3403 | 0.4331 | 0.2274 | 0.095* | |
H17B | 0.4401 | 0.5199 | 0.1945 | 0.095* | |
C21 | 0.2423 (2) | 0.7032 (2) | 0.03774 (15) | 0.0612 (8) | |
H21A | 0.1655 | 0.7229 | 0.0645 | 0.073* | |
C22 | 0.2165 (2) | 0.6131 (2) | −0.02790 (15) | 0.0749 (9) | |
H22A | 0.1801 | 0.5430 | −0.0034 | 0.090* | |
H22B | 0.2922 | 0.5889 | −0.0529 | 0.090* | |
C23 | 0.1324 (3) | 0.6613 (3) | −0.09346 (15) | 0.0853 (10) | |
H23A | 0.1225 | 0.6018 | −0.1359 | 0.102* | |
H23B | 0.0536 | 0.6771 | −0.0699 | 0.102* | |
C24 | 0.1821 (3) | 0.7749 (3) | −0.13043 (16) | 0.0897 (10) | |
H24A | 0.2562 | 0.7573 | −0.1597 | 0.108* | |
H24B | 0.1241 | 0.8070 | −0.1690 | 0.108* | |
C25 | 0.2072 (3) | 0.8660 (3) | −0.06500 (16) | 0.0888 (10) | |
H25A | 0.1316 | 0.8899 | −0.0398 | 0.107* | |
H25B | 0.2435 | 0.9362 | −0.0895 | 0.107* | |
C26 | 0.2922 (3) | 0.8166 (2) | 0.00022 (15) | 0.0752 (8) | |
H26A | 0.3705 | 0.8002 | −0.0240 | 0.090* | |
H26B | 0.3034 | 0.8760 | 0.0426 | 0.090* | |
C27 | 0.3273 (2) | 0.6535 (2) | 0.10205 (15) | 0.0709 (8) | |
H27A | 0.4003 | 0.6254 | 0.0755 | 0.085* | |
H27B | 0.3500 | 0.7173 | 0.1389 | 0.085* | |
C31 | 0.1026 (3) | 0.5198 (2) | 0.24604 (16) | 0.0699 (8) | |
H31A | 0.1392 | 0.4423 | 0.2586 | 0.084* | |
C32 | 0.0431 (3) | 0.5667 (3) | 0.32333 (16) | 0.0922 (10) | |
H32A | 0.1036 | 0.5731 | 0.3660 | 0.111* | |
H32B | 0.0112 | 0.6459 | 0.3130 | 0.111* | |
C33 | −0.0583 (4) | 0.4866 (3) | 0.35229 (19) | 0.1144 (12) | |
H33A | −0.0252 | 0.4099 | 0.3683 | 0.137* | |
H33B | −0.0964 | 0.5219 | 0.3998 | 0.137* | |
C34 | −0.1519 (3) | 0.4683 (3) | 0.2867 (2) | 0.1131 (12) | |
H34A | −0.2129 | 0.4128 | 0.3058 | 0.136* | |
H34B | −0.1914 | 0.5436 | 0.2748 | 0.136* | |
C35 | −0.0942 (3) | 0.4203 (3) | 0.2102 (2) | 0.1004 (10) | |
H35A | −0.1549 | 0.4140 | 0.1677 | 0.120* | |
H35B | −0.0627 | 0.3410 | 0.2208 | 0.120* | |
C36 | 0.0085 (3) | 0.5008 (3) | 0.18090 (16) | 0.0867 (10) | |
H36A | 0.0463 | 0.4651 | 0.1334 | 0.104* | |
H36B | −0.0246 | 0.5773 | 0.1647 | 0.104* | |
C37 | 0.2022 (3) | 0.6028 (2) | 0.21770 (15) | 0.0780 (9) | |
H37A | 0.1661 | 0.6776 | 0.2007 | 0.094* | |
H37B | 0.2553 | 0.6195 | 0.2634 | 0.094* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0711 (18) | 0.0585 (16) | 0.0675 (14) | −0.0008 (14) | 0.0078 (13) | 0.0070 (13) |
C11 | 0.068 (2) | 0.075 (2) | 0.076 (2) | 0.010 (2) | 0.0033 (16) | 0.0120 (18) |
C12 | 0.080 (3) | 0.076 (2) | 0.110 (2) | 0.017 (2) | −0.002 (2) | −0.005 (2) |
C13 | 0.105 (3) | 0.087 (3) | 0.125 (3) | 0.026 (2) | −0.007 (2) | −0.013 (2) |
C14 | 0.110 (4) | 0.099 (3) | 0.138 (3) | 0.035 (3) | 0.011 (2) | −0.002 (2) |
C15 | 0.083 (3) | 0.132 (4) | 0.141 (3) | 0.042 (3) | 0.015 (2) | 0.016 (3) |
C16 | 0.069 (3) | 0.104 (3) | 0.119 (3) | 0.017 (2) | −0.0029 (19) | 0.020 (2) |
C17 | 0.084 (2) | 0.079 (2) | 0.0742 (19) | 0.0019 (19) | −0.0086 (17) | 0.015 (2) |
C21 | 0.062 (2) | 0.057 (2) | 0.0643 (17) | 0.0004 (16) | 0.0043 (15) | 0.0047 (16) |
C22 | 0.082 (2) | 0.068 (2) | 0.0740 (18) | −0.0075 (19) | 0.0061 (18) | −0.0043 (17) |
C23 | 0.095 (3) | 0.098 (3) | 0.0627 (18) | −0.015 (2) | −0.0027 (19) | −0.0078 (19) |
C24 | 0.091 (3) | 0.108 (3) | 0.070 (2) | 0.001 (2) | 0.0000 (19) | 0.009 (2) |
C25 | 0.101 (3) | 0.083 (2) | 0.083 (2) | 0.001 (2) | 0.0049 (19) | 0.0181 (19) |
C26 | 0.081 (2) | 0.064 (2) | 0.0804 (18) | −0.0085 (19) | −0.0002 (18) | 0.0058 (16) |
C27 | 0.068 (2) | 0.064 (2) | 0.0805 (18) | −0.0067 (17) | 0.0011 (17) | 0.0050 (17) |
C31 | 0.082 (2) | 0.058 (2) | 0.0692 (19) | 0.0072 (18) | 0.0093 (17) | 0.0092 (16) |
C32 | 0.117 (3) | 0.084 (2) | 0.076 (2) | −0.004 (2) | 0.0204 (19) | 0.0047 (19) |
C33 | 0.127 (4) | 0.110 (3) | 0.106 (3) | 0.008 (3) | 0.038 (3) | 0.023 (2) |
C34 | 0.095 (3) | 0.096 (3) | 0.148 (3) | 0.007 (2) | 0.041 (3) | 0.027 (3) |
C35 | 0.083 (3) | 0.091 (3) | 0.127 (3) | −0.006 (2) | 0.006 (2) | 0.009 (2) |
C36 | 0.085 (3) | 0.088 (3) | 0.087 (2) | −0.003 (2) | 0.012 (2) | 0.0021 (19) |
C37 | 0.097 (2) | 0.069 (2) | 0.0683 (17) | 0.000 (2) | 0.0092 (18) | −0.0028 (16) |
N1—C17 | 1.468 (3) | C23—H23B | 0.9700 |
N1—C27 | 1.468 (3) | C24—C25 | 1.508 (3) |
N1—C37 | 1.474 (3) | C24—H24A | 0.9700 |
C11—C12 | 1.503 (3) | C24—H24B | 0.9700 |
C11—C16 | 1.518 (3) | C25—C26 | 1.527 (3) |
C11—C17 | 1.521 (3) | C25—H25A | 0.9700 |
C11—H11A | 0.9800 | C25—H25B | 0.9700 |
C12—C13 | 1.513 (3) | C26—H26A | 0.9700 |
C12—H12A | 0.9700 | C26—H26B | 0.9700 |
C12—H12B | 0.9700 | C27—H27A | 0.9700 |
C13—C14 | 1.498 (4) | C27—H27B | 0.9700 |
C13—H13A | 0.9700 | C31—C36 | 1.506 (3) |
C13—H13B | 0.9700 | C31—C37 | 1.514 (3) |
C14—C15 | 1.511 (4) | C31—C32 | 1.521 (3) |
C14—H14A | 0.9700 | C31—H31A | 0.9800 |
C14—H14B | 0.9700 | C32—C33 | 1.513 (4) |
C15—C16 | 1.534 (4) | C32—H32A | 0.9700 |
C15—H15A | 0.9700 | C32—H32B | 0.9700 |
C15—H15B | 0.9700 | C33—C34 | 1.506 (4) |
C16—H16A | 0.9700 | C33—H33A | 0.9700 |
C16—H16B | 0.9700 | C33—H33B | 0.9700 |
C17—H17A | 0.9700 | C34—C35 | 1.505 (4) |
C17—H17B | 0.9700 | C34—H34A | 0.9700 |
C21—C22 | 1.503 (3) | C34—H34B | 0.9700 |
C21—C26 | 1.516 (3) | C35—C36 | 1.527 (3) |
C21—C27 | 1.518 (3) | C35—H35A | 0.9700 |
C21—H21A | 0.9800 | C35—H35B | 0.9700 |
C22—C23 | 1.520 (3) | C36—H36A | 0.9700 |
C22—H22A | 0.9700 | C36—H36B | 0.9700 |
C22—H22B | 0.9700 | C37—H37A | 0.9700 |
C23—C24 | 1.513 (3) | C37—H37B | 0.9700 |
C23—H23A | 0.9700 | ||
C17—N1—C27 | 111.3 (2) | C23—C24—H24A | 109.5 |
C17—N1—C37 | 111.58 (19) | C25—C24—H24B | 109.5 |
C27—N1—C37 | 110.3 (2) | C23—C24—H24B | 109.5 |
C12—C11—C16 | 110.8 (2) | H24A—C24—H24B | 108.1 |
C12—C11—C17 | 112.1 (2) | C24—C25—C26 | 111.5 (2) |
C16—C11—C17 | 111.0 (2) | C24—C25—H25A | 109.3 |
C12—C11—H11A | 107.6 | C26—C25—H25A | 109.3 |
C16—C11—H11A | 107.6 | C24—C25—H25B | 109.3 |
C17—C11—H11A | 107.6 | C26—C25—H25B | 109.3 |
C11—C12—C13 | 113.0 (3) | H25A—C25—H25B | 108.0 |
C11—C12—H12A | 109.0 | C21—C26—C25 | 111.4 (2) |
C13—C12—H12A | 109.0 | C21—C26—H26A | 109.4 |
C11—C12—H12B | 109.0 | C25—C26—H26A | 109.4 |
C13—C12—H12B | 109.0 | C21—C26—H26B | 109.4 |
H12A—C12—H12B | 107.8 | C25—C26—H26B | 109.4 |
C14—C13—C12 | 111.3 (3) | H26A—C26—H26B | 108.0 |
C14—C13—H13A | 109.4 | N1—C27—C21 | 113.8 (2) |
C12—C13—H13A | 109.4 | N1—C27—H27A | 108.8 |
C14—C13—H13B | 109.4 | C21—C27—H27A | 108.8 |
C12—C13—H13B | 109.4 | N1—C27—H27B | 108.8 |
H13A—C13—H13B | 108.0 | C21—C27—H27B | 108.8 |
C13—C14—C15 | 110.8 (3) | H27A—C27—H27B | 107.7 |
C13—C14—H14A | 109.5 | C36—C31—C37 | 111.8 (2) |
C15—C14—H14A | 109.5 | C36—C31—C32 | 109.9 (3) |
C13—C14—H14B | 109.5 | C37—C31—C32 | 110.9 (2) |
C15—C14—H14B | 109.5 | C36—C31—H31A | 108.0 |
H14A—C14—H14B | 108.1 | C37—C31—H31A | 108.0 |
C14—C15—C16 | 111.9 (3) | C32—C31—H31A | 108.0 |
C14—C15—H15A | 109.2 | C33—C32—C31 | 112.1 (3) |
C16—C15—H15A | 109.2 | C33—C32—H32A | 109.2 |
C14—C15—H15B | 109.2 | C31—C32—H32A | 109.2 |
C16—C15—H15B | 109.2 | C33—C32—H32B | 109.2 |
H15A—C15—H15B | 107.9 | C31—C32—H32B | 109.2 |
C11—C16—C15 | 111.3 (3) | H32A—C32—H32B | 107.9 |
C11—C16—H16A | 109.4 | C34—C33—C32 | 111.4 (3) |
C15—C16—H16A | 109.4 | C34—C33—H33A | 109.3 |
C11—C16—H16B | 109.4 | C32—C33—H33A | 109.3 |
C15—C16—H16B | 109.4 | C34—C33—H33B | 109.3 |
H16A—C16—H16B | 108.0 | C32—C33—H33B | 109.3 |
N1—C17—C11 | 113.6 (2) | H33A—C33—H33B | 108.0 |
N1—C17—H17A | 108.8 | C35—C34—C33 | 110.7 (3) |
C11—C17—H17A | 108.8 | C35—C34—H34A | 109.5 |
N1—C17—H17B | 108.8 | C33—C34—H34A | 109.5 |
C11—C17—H17B | 108.8 | C35—C34—H34B | 109.5 |
H17A—C17—H17B | 107.7 | C33—C34—H34B | 109.5 |
C22—C21—C26 | 110.0 (2) | H34A—C34—H34B | 108.1 |
C22—C21—C27 | 111.5 (2) | C34—C35—C36 | 111.4 (3) |
C26—C21—C27 | 111.4 (2) | C34—C35—H35A | 109.3 |
C22—C21—H21A | 107.9 | C36—C35—H35A | 109.3 |
C26—C21—H21A | 107.9 | C34—C35—H35B | 109.3 |
C27—C21—H21A | 107.9 | C36—C35—H35B | 109.3 |
C21—C22—C23 | 112.5 (2) | H35A—C35—H35B | 108.0 |
C21—C22—H22A | 109.1 | C31—C36—C35 | 111.9 (2) |
C23—C22—H22A | 109.1 | C31—C36—H36A | 109.2 |
C21—C22—H22B | 109.1 | C35—C36—H36A | 109.2 |
C23—C22—H22B | 109.1 | C31—C36—H36B | 109.2 |
H22A—C22—H22B | 107.8 | C35—C36—H36B | 109.2 |
C24—C23—C22 | 111.2 (2) | H36A—C36—H36B | 107.9 |
C24—C23—H23A | 109.4 | N1—C37—C31 | 114.1 (2) |
C22—C23—H23A | 109.4 | N1—C37—H37A | 108.7 |
C24—C23—H23B | 109.4 | C31—C37—H37A | 108.7 |
C22—C23—H23B | 109.4 | N1—C37—H37B | 108.7 |
H23A—C23—H23B | 108.0 | C31—C37—H37B | 108.7 |
C25—C24—C23 | 110.6 (2) | H37A—C37—H37B | 107.6 |
C25—C24—H24A | 109.5 | ||
C16—C11—C12—C13 | −53.9 (3) | C27—C21—C26—C25 | 179.5 (2) |
C17—C11—C12—C13 | −178.5 (2) | C24—C25—C26—C21 | −56.3 (3) |
C11—C12—C13—C14 | 55.6 (3) | C17—N1—C27—C21 | 151.4 (2) |
C12—C13—C14—C15 | −55.4 (4) | C37—N1—C27—C21 | −84.2 (3) |
C13—C14—C15—C16 | 55.5 (4) | C22—C21—C27—N1 | −66.1 (3) |
C12—C11—C16—C15 | 52.8 (3) | C26—C21—C27—N1 | 170.5 (2) |
C17—C11—C16—C15 | 177.9 (2) | C36—C31—C32—C33 | 54.8 (3) |
C14—C15—C16—C11 | −54.4 (4) | C37—C31—C32—C33 | 179.0 (3) |
C27—N1—C17—C11 | −83.3 (3) | C31—C32—C33—C34 | −55.9 (4) |
C37—N1—C17—C11 | 153.0 (2) | C32—C33—C34—C35 | 55.6 (4) |
C12—C11—C17—N1 | −66.2 (3) | C33—C34—C35—C36 | −55.4 (4) |
C16—C11—C17—N1 | 169.3 (2) | C37—C31—C36—C35 | −178.2 (2) |
C26—C21—C22—C23 | −55.3 (3) | C32—C31—C36—C35 | −54.5 (3) |
C27—C21—C22—C23 | −179.5 (2) | C34—C35—C36—C31 | 55.9 (4) |
C21—C22—C23—C24 | 55.7 (3) | C17—N1—C37—C31 | −82.0 (3) |
C22—C23—C24—C25 | −54.9 (3) | C27—N1—C37—C31 | 153.7 (2) |
C23—C24—C25—C26 | 55.6 (3) | C36—C31—C37—N1 | −64.9 (3) |
C22—C21—C26—C25 | 55.3 (3) | C32—C31—C37—N1 | 172.0 (2) |