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
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.034
- wR factor = 0.089
- Data-to-parameter ratio = 17.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.99
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 33.70 From the CIF: _reflns_number_total 4004 Count of symmetry unique reflns 4056 Completeness (_total/calc) 98.72% 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 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 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, 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) |
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