Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803023808/hg6002sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803023808/hg6002Isup2.hkl |
CCDC reference: 227028
Data collection: COLLECT (Nonius, 2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C22H30N2O | F(000) = 736 |
Mr = 338.48 | Dx = 1.233 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3909 reflections |
a = 10.236 (2) Å | θ = 2.5–34.3° |
b = 10.947 (2) Å | µ = 0.08 mm−1 |
c = 16.278 (2) Å | T = 100 K |
V = 1824.0 (5) Å3 | Prism, colorless |
Z = 4 | 0.40 × 0.40 × 0.37 mm |
Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler) diffractometer | 3769 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.017 |
Graphite monochromator | θmax = 33.7°, θmin = 2.7° |
ω scans with κ offsets | h = −15→15 |
22786 measured reflections | k = −17→17 |
4004 independent reflections | l = −24→24 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.0457P)2 + 0.2882P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
4004 reflections | Δρmax = 0.29 e Å−3 |
227 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.019 (2) |
Experimental. The completeness of the data to θmax = 30° is 0.998. |
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 | 0.74242 (9) | 0.49036 (8) | 0.44079 (5) | 0.02074 (16) | |
N1 | 0.62550 (10) | 0.33718 (9) | 0.49936 (6) | 0.01840 (17) | |
N2 | 0.49430 (8) | 0.51583 (8) | 0.62845 (5) | 0.01491 (16) | |
C2 | 0.37991 (10) | 0.59091 (11) | 0.64800 (7) | 0.01779 (18) | |
H2A | 0.3949 | 0.6343 | 0.7005 | 0.021* | |
H2B | 0.3026 | 0.5376 | 0.6549 | 0.021* | |
C3 | 0.35341 (11) | 0.68355 (11) | 0.58049 (7) | 0.0211 (2) | |
H3A | 0.2791 | 0.7362 | 0.5966 | 0.025* | |
H3B | 0.3293 | 0.6403 | 0.5293 | 0.025* | |
C4 | 0.47379 (11) | 0.76248 (10) | 0.56506 (7) | 0.0203 (2) | |
H4A | 0.4910 | 0.8145 | 0.6136 | 0.024* | |
H4B | 0.4583 | 0.8165 | 0.5173 | 0.024* | |
C5 | 0.59191 (11) | 0.68044 (10) | 0.54836 (6) | 0.01615 (18) | |
H5A | 0.6705 | 0.7324 | 0.5424 | 0.019* | |
H5B | 0.5782 | 0.6372 | 0.4956 | 0.019* | |
C6 | 0.61704 (9) | 0.58556 (9) | 0.61606 (6) | 0.01389 (16) | |
C7 | 0.72458 (9) | 0.49389 (10) | 0.58792 (6) | 0.01497 (17) | |
H7 | 0.8094 | 0.5391 | 0.5854 | 0.018* | |
C8 | 0.74102 (11) | 0.38808 (10) | 0.64840 (7) | 0.01892 (19) | |
H8A | 0.8096 | 0.3313 | 0.6290 | 0.023* | |
H8B | 0.7664 | 0.4193 | 0.7032 | 0.023* | |
C9 | 0.60958 (11) | 0.32286 (10) | 0.65307 (7) | 0.01895 (19) | |
H9 | 0.6171 | 0.2547 | 0.6937 | 0.023* | |
C10 | 0.50666 (11) | 0.41230 (10) | 0.68404 (6) | 0.01848 (19) | |
H10A | 0.4214 | 0.3701 | 0.6886 | 0.022* | |
H10B | 0.5314 | 0.4418 | 0.7394 | 0.022* | |
C11 | 0.57332 (11) | 0.26788 (10) | 0.56941 (7) | 0.01833 (19) | |
H11 | 0.4759 | 0.2680 | 0.5649 | 0.022* | |
C12 | 0.61998 (13) | 0.13444 (10) | 0.56258 (8) | 0.0242 (2) | |
H12A | 0.7158 | 0.1315 | 0.5707 | 0.029* | |
H12B | 0.5788 | 0.0856 | 0.6067 | 0.029* | |
C13 | 0.58647 (13) | 0.07773 (11) | 0.47943 (9) | 0.0260 (2) | |
H13A | 0.6257 | −0.0047 | 0.4757 | 0.031* | |
H13B | 0.4905 | 0.0691 | 0.4745 | 0.031* | |
C14 | 0.63753 (13) | 0.15688 (12) | 0.40938 (8) | 0.0256 (2) | |
H14A | 0.7342 | 0.1553 | 0.4093 | 0.031* | |
H14B | 0.6067 | 0.1236 | 0.3563 | 0.031* | |
C15 | 0.59018 (13) | 0.28802 (11) | 0.41889 (7) | 0.0232 (2) | |
H15A | 0.6295 | 0.3393 | 0.3753 | 0.028* | |
H15B | 0.4941 | 0.2906 | 0.4123 | 0.028* | |
C17 | 0.69769 (10) | 0.44134 (9) | 0.50281 (6) | 0.01569 (17) | |
C18 | 0.66307 (10) | 0.65137 (10) | 0.69704 (6) | 0.01668 (18) | |
H18A | 0.5932 | 0.7080 | 0.7149 | 0.020* | |
H18B | 0.6735 | 0.5890 | 0.7406 | 0.020* | |
C19 | 0.78917 (11) | 0.72257 (10) | 0.69026 (6) | 0.01696 (18) | |
C20 | 0.91009 (11) | 0.66757 (11) | 0.70535 (7) | 0.0200 (2) | |
H20 | 0.9131 | 0.5842 | 0.7213 | 0.024* | |
C21 | 1.02617 (11) | 0.73267 (13) | 0.69741 (7) | 0.0236 (2) | |
H21 | 1.1072 | 0.6935 | 0.7082 | 0.028* | |
C22 | 1.02430 (12) | 0.85501 (13) | 0.67375 (7) | 0.0242 (2) | |
H22 | 1.1035 | 0.8991 | 0.6670 | 0.029* | |
C23 | 0.90468 (13) | 0.91144 (12) | 0.66014 (7) | 0.0247 (2) | |
H23 | 0.9021 | 0.9951 | 0.6448 | 0.030* | |
C24 | 0.78853 (12) | 0.84648 (11) | 0.66883 (7) | 0.0208 (2) | |
H24 | 0.7076 | 0.8869 | 0.6601 | 0.025* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0245 (4) | 0.0217 (4) | 0.0161 (3) | −0.0010 (3) | 0.0040 (3) | −0.0002 (3) |
N1 | 0.0248 (4) | 0.0150 (4) | 0.0154 (4) | −0.0012 (3) | −0.0003 (3) | −0.0015 (3) |
N2 | 0.0136 (3) | 0.0153 (3) | 0.0159 (4) | −0.0005 (3) | 0.0013 (3) | 0.0005 (3) |
C2 | 0.0150 (4) | 0.0196 (4) | 0.0187 (4) | −0.0004 (4) | 0.0021 (3) | −0.0026 (4) |
C3 | 0.0161 (4) | 0.0225 (5) | 0.0247 (5) | 0.0040 (4) | −0.0011 (4) | −0.0011 (4) |
C4 | 0.0217 (5) | 0.0161 (4) | 0.0231 (5) | 0.0029 (4) | −0.0001 (4) | 0.0014 (4) |
C5 | 0.0175 (4) | 0.0160 (4) | 0.0149 (4) | 0.0000 (4) | 0.0008 (3) | 0.0021 (3) |
C6 | 0.0137 (4) | 0.0151 (4) | 0.0129 (4) | −0.0001 (3) | 0.0006 (3) | −0.0007 (3) |
C7 | 0.0148 (4) | 0.0164 (4) | 0.0137 (4) | 0.0008 (4) | −0.0004 (3) | −0.0009 (3) |
C8 | 0.0194 (4) | 0.0203 (5) | 0.0170 (4) | 0.0034 (4) | −0.0026 (4) | 0.0019 (4) |
C9 | 0.0228 (5) | 0.0171 (4) | 0.0169 (4) | 0.0011 (4) | 0.0002 (4) | 0.0043 (4) |
C10 | 0.0215 (4) | 0.0186 (4) | 0.0153 (4) | −0.0014 (4) | 0.0033 (3) | 0.0034 (4) |
C11 | 0.0199 (4) | 0.0145 (4) | 0.0205 (4) | 0.0000 (4) | 0.0012 (4) | 0.0019 (4) |
C12 | 0.0272 (5) | 0.0143 (4) | 0.0310 (6) | 0.0019 (4) | 0.0002 (5) | 0.0013 (4) |
C13 | 0.0247 (5) | 0.0152 (4) | 0.0381 (6) | −0.0002 (4) | 0.0009 (5) | −0.0051 (4) |
C14 | 0.0257 (5) | 0.0222 (5) | 0.0288 (6) | −0.0014 (5) | 0.0010 (4) | −0.0108 (4) |
C15 | 0.0308 (6) | 0.0199 (5) | 0.0190 (5) | −0.0017 (5) | −0.0032 (4) | −0.0045 (4) |
C17 | 0.0153 (4) | 0.0156 (4) | 0.0161 (4) | 0.0020 (3) | 0.0006 (3) | −0.0013 (3) |
C18 | 0.0165 (4) | 0.0191 (4) | 0.0144 (4) | −0.0017 (4) | 0.0005 (3) | −0.0020 (3) |
C19 | 0.0179 (4) | 0.0196 (4) | 0.0133 (4) | −0.0025 (4) | −0.0006 (3) | −0.0027 (4) |
C20 | 0.0186 (4) | 0.0234 (5) | 0.0180 (4) | −0.0011 (4) | −0.0019 (4) | −0.0020 (4) |
C21 | 0.0172 (4) | 0.0338 (6) | 0.0197 (5) | −0.0020 (4) | −0.0009 (4) | −0.0036 (5) |
C22 | 0.0220 (5) | 0.0342 (6) | 0.0165 (4) | −0.0100 (5) | −0.0003 (4) | −0.0014 (5) |
C23 | 0.0272 (5) | 0.0241 (5) | 0.0230 (5) | −0.0079 (5) | −0.0031 (4) | 0.0019 (4) |
C24 | 0.0204 (4) | 0.0205 (5) | 0.0214 (5) | −0.0025 (4) | −0.0020 (4) | −0.0007 (4) |
O1—C17 | 1.2315 (13) | C10—H10A | 0.99 |
N1—C17 | 1.3599 (14) | C10—H10B | 0.99 |
N1—C15 | 1.4615 (14) | C11—C12 | 1.5409 (16) |
N1—C11 | 1.4700 (14) | C11—H11 | 1.00 |
N2—C10 | 1.4557 (14) | C12—C13 | 1.5281 (18) |
N2—C2 | 1.4655 (14) | C12—H12A | 0.99 |
N2—C6 | 1.4839 (13) | C12—H12B | 0.99 |
C2—C3 | 1.5197 (16) | C13—C14 | 1.5245 (19) |
C2—H2A | 0.99 | C13—H13A | 0.99 |
C2—H2B | 0.99 | C13—H13B | 0.99 |
C3—C4 | 1.5258 (17) | C14—C15 | 1.5230 (18) |
C3—H3A | 0.99 | C14—H14A | 0.99 |
C3—H3B | 0.99 | C14—H14B | 0.99 |
C4—C5 | 1.5305 (16) | C15—H15A | 0.99 |
C4—H4A | 0.99 | C15—H15B | 0.99 |
C4—H4B | 0.99 | C18—C19 | 1.5119 (15) |
C5—C6 | 1.5360 (14) | C18—H18A | 0.99 |
C5—H5A | 0.99 | C18—H18B | 0.99 |
C5—H5B | 0.99 | C19—C20 | 1.3982 (16) |
C6—C7 | 1.5584 (14) | C19—C24 | 1.4006 (17) |
C6—C18 | 1.5744 (14) | C20—C21 | 1.3916 (17) |
C7—C17 | 1.5251 (14) | C20—H20 | 0.95 |
C7—C8 | 1.5295 (15) | C21—C22 | 1.394 (2) |
C7—H7 | 1.00 | C21—H21 | 0.95 |
C8—C9 | 1.5251 (16) | C22—C23 | 1.3892 (18) |
C8—H8A | 0.99 | C22—H22 | 0.95 |
C8—H8B | 0.99 | C23—C24 | 1.3926 (17) |
C9—C10 | 1.5240 (16) | C23—H23 | 0.95 |
C9—C11 | 1.5345 (16) | C24—H24 | 0.95 |
C9—H9 | 1.00 | ||
C17—N1—C15 | 118.69 (9) | H10A—C10—H10B | 108.1 |
C17—N1—C11 | 126.74 (9) | N1—C11—C9 | 113.46 (9) |
C15—N1—C11 | 114.54 (9) | N1—C11—C12 | 108.70 (9) |
C10—N2—C2 | 111.79 (8) | C9—C11—C12 | 111.15 (9) |
C10—N2—C6 | 114.29 (8) | N1—C11—H11 | 107.8 |
C2—N2—C6 | 114.67 (9) | C9—C11—H11 | 107.8 |
N2—C2—C3 | 111.09 (9) | C12—C11—H11 | 107.8 |
N2—C2—H2A | 109.4 | C13—C12—C11 | 112.30 (10) |
C3—C2—H2A | 109.4 | C13—C12—H12A | 109.1 |
N2—C2—H2B | 109.4 | C11—C12—H12A | 109.1 |
C3—C2—H2B | 109.4 | C13—C12—H12B | 109.1 |
H2A—C2—H2B | 108.0 | C11—C12—H12B | 109.1 |
C2—C3—C4 | 110.66 (9) | H12A—C12—H12B | 107.9 |
C2—C3—H3A | 109.5 | C14—C13—C12 | 110.77 (10) |
C4—C3—H3A | 109.5 | C14—C13—H13A | 109.5 |
C2—C3—H3B | 109.5 | C12—C13—H13A | 109.5 |
C4—C3—H3B | 109.5 | C14—C13—H13B | 109.5 |
H3A—C3—H3B | 108.1 | C12—C13—H13B | 109.5 |
C3—C4—C5 | 109.56 (9) | H13A—C13—H13B | 108.1 |
C3—C4—H4A | 109.8 | C15—C14—C13 | 110.52 (10) |
C5—C4—H4A | 109.8 | C15—C14—H14A | 109.5 |
C3—C4—H4B | 109.8 | C13—C14—H14A | 109.5 |
C5—C4—H4B | 109.8 | C15—C14—H14B | 109.5 |
H4A—C4—H4B | 108.2 | C13—C14—H14B | 109.5 |
C4—C5—C6 | 113.69 (9) | H14A—C14—H14B | 108.1 |
C4—C5—H5A | 108.8 | N1—C15—C14 | 111.07 (10) |
C6—C5—H5A | 108.8 | N1—C15—H15A | 109.4 |
C4—C5—H5B | 108.8 | C14—C15—H15A | 109.4 |
C6—C5—H5B | 108.8 | N1—C15—H15B | 109.4 |
H5A—C5—H5B | 107.7 | C14—C15—H15B | 109.4 |
N2—C6—C5 | 107.67 (8) | H15A—C15—H15B | 108.0 |
N2—C6—C7 | 107.86 (8) | O1—C17—N1 | 122.24 (10) |
C5—C6—C7 | 110.05 (8) | O1—C17—C7 | 120.88 (9) |
N2—C6—C18 | 112.02 (8) | N1—C17—C7 | 116.86 (9) |
C5—C6—C18 | 109.96 (8) | C19—C18—C6 | 115.48 (8) |
C7—C6—C18 | 109.23 (8) | C19—C18—H18A | 108.4 |
C17—C7—C8 | 108.60 (9) | C6—C18—H18A | 108.4 |
C17—C7—C6 | 112.48 (8) | C19—C18—H18B | 108.4 |
C8—C7—C6 | 112.10 (8) | C6—C18—H18B | 108.4 |
C17—C7—H7 | 107.8 | H18A—C18—H18B | 107.5 |
C8—C7—H7 | 107.8 | C20—C19—C24 | 117.71 (10) |
C6—C7—H7 | 107.8 | C20—C19—C18 | 121.39 (10) |
C9—C8—C7 | 106.83 (8) | C24—C19—C18 | 120.90 (10) |
C9—C8—H8A | 110.4 | C21—C20—C19 | 121.27 (11) |
C7—C8—H8A | 110.4 | C21—C20—H20 | 119.4 |
C9—C8—H8B | 110.4 | C19—C20—H20 | 119.4 |
C7—C8—H8B | 110.4 | C20—C21—C22 | 120.40 (12) |
H8A—C8—H8B | 108.6 | C20—C21—H21 | 119.8 |
C10—C9—C8 | 109.00 (9) | C22—C21—H21 | 119.8 |
C10—C9—C11 | 112.23 (9) | C23—C22—C21 | 118.92 (11) |
C8—C9—C11 | 110.65 (9) | C23—C22—H22 | 120.5 |
C10—C9—H9 | 108.3 | C21—C22—H22 | 120.5 |
C8—C9—H9 | 108.3 | C22—C23—C24 | 120.62 (11) |
C11—C9—H9 | 108.3 | C22—C23—H23 | 119.7 |
N2—C10—C9 | 110.78 (8) | C24—C23—H23 | 119.7 |
N2—C10—H10A | 109.5 | C23—C24—C19 | 121.05 (11) |
C9—C10—H10A | 109.5 | C23—C24—H24 | 119.5 |
N2—C10—H10B | 109.5 | C19—C24—H24 | 119.5 |
C9—C10—H10B | 109.5 | ||
C10—N2—C2—C3 | −169.16 (9) | C10—C9—C11—N1 | 91.72 (11) |
C6—N2—C2—C3 | 58.68 (11) | C8—C9—C11—N1 | −30.28 (12) |
N2—C2—C3—C4 | −55.83 (12) | C10—C9—C11—C12 | −145.41 (10) |
C2—C3—C4—C5 | 53.67 (12) | C8—C9—C11—C12 | 92.60 (11) |
C3—C4—C5—C6 | −54.56 (12) | N1—C11—C12—C13 | −53.80 (13) |
C10—N2—C6—C5 | 173.04 (8) | C9—C11—C12—C13 | −179.37 (10) |
C2—N2—C6—C5 | −56.01 (10) | C11—C12—C13—C14 | 53.61 (14) |
C10—N2—C6—C7 | 54.30 (10) | C12—C13—C14—C15 | −53.09 (14) |
C2—N2—C6—C7 | −174.74 (8) | C17—N1—C15—C14 | 123.27 (11) |
C10—N2—C6—C18 | −65.94 (11) | C11—N1—C15—C14 | −58.69 (13) |
C2—N2—C6—C18 | 65.02 (11) | C13—C14—C15—N1 | 54.92 (14) |
C4—C5—C6—N2 | 53.98 (11) | C15—N1—C17—O1 | −5.57 (16) |
C4—C5—C6—C7 | 171.30 (8) | C11—N1—C17—O1 | 176.65 (10) |
C4—C5—C6—C18 | −68.32 (11) | C15—N1—C17—C7 | 176.07 (10) |
N2—C6—C7—C17 | 67.21 (10) | C11—N1—C17—C7 | −1.71 (15) |
C5—C6—C7—C17 | −49.99 (11) | C8—C7—C17—O1 | −143.40 (10) |
C18—C6—C7—C17 | −170.81 (8) | C6—C7—C17—O1 | 91.93 (12) |
N2—C6—C7—C8 | −55.52 (10) | C8—C7—C17—N1 | 34.98 (12) |
C5—C6—C7—C8 | −172.72 (8) | C6—C7—C17—N1 | −89.69 (11) |
C18—C6—C7—C8 | 66.46 (11) | N2—C6—C18—C19 | 178.82 (9) |
C17—C7—C8—C9 | −65.04 (10) | C5—C6—C18—C19 | −61.49 (11) |
C6—C7—C8—C9 | 59.86 (11) | C7—C6—C18—C19 | 59.38 (11) |
C7—C8—C9—C10 | −60.62 (11) | C6—C18—C19—C20 | −89.33 (12) |
C7—C8—C9—C11 | 63.25 (11) | C6—C18—C19—C24 | 90.91 (12) |
C2—N2—C10—C9 | 169.18 (9) | C24—C19—C20—C21 | −1.57 (15) |
C6—N2—C10—C9 | −58.47 (11) | C18—C19—C20—C21 | 178.65 (11) |
C8—C9—C10—N2 | 60.58 (11) | C19—C20—C21—C22 | −0.22 (17) |
C11—C9—C10—N2 | −62.36 (12) | C20—C21—C22—C23 | 1.48 (17) |
C17—N1—C11—C9 | −1.00 (15) | C21—C22—C23—C24 | −0.90 (17) |
C15—N1—C11—C9 | −178.86 (10) | C22—C23—C24—C19 | −0.94 (17) |
C17—N1—C11—C12 | −125.21 (12) | C20—C19—C24—C23 | 2.15 (16) |
C15—N1—C11—C12 | 56.93 (13) | C18—C19—C24—C23 | −178.07 (10) |