Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802004956/ww6013sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802004956/ww6013Isup2.hkl |
CCDC reference: 183820
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.045
- wR factor = 0.103
- Data-to-parameter ratio = 14.6
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Data collection: CAD-4-PC (Enraf-Nonius, 1989); cell refinement: CAD-4-PC; data reduction: TEXSAN (Molecular Structure Corporation, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.
C21H25IN2O | Z = 2 |
Mr = 448.33 | F(000) = 452 |
Triclinic, P1 | Dx = 1.510 Mg m−3 |
Hall symbol: -P 1 | Melting point: 437-438K K |
a = 9.168 (3) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 10.884 (1) Å | Cell parameters from 25 reflections |
c = 10.969 (2) Å | θ = 0.0–25.0° |
α = 84.83 (1)° | µ = 1.63 mm−1 |
β = 82.21 (2)° | T = 293 K |
γ = 65.51 (2)° | Plate, brown |
V = 986.2 (4) Å3 | 0.3 × 0.2 × 0.2 mm |
Enraf-Nonius CAD-4 diffractometer | 2963 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
ω/2θ scans | h = −10→10 |
Absorption correction: ψ scan (North et al., 1968) | k = −12→12 |
Tmin = 0.682, Tmax = 0.721 | l = 0→13 |
3613 measured reflections | 5 standard reflections every 300 reflections |
3417 independent reflections | intensity decay: 0.0005% |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.02P)2 + 1.98P] where P = (Fo2 + 2Fc2)/3 |
3377 reflections | (Δ/σ)max < 0.001 |
231 parameters | Δρmax = 0.97 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Experimental. All commercially available reagents were used as supplied. 1H NMR spectra were obtained from CDCl3 solution using TMS as an internal standard on a Bruker FC-80 A instrument. Mass spectra (MS) were measured on an HP-5988 A GCMS spectrometer. CHN analyses were performed on a Carlo Erba 1106 elemental analyzer. FT–IR spectra were taken on a Nicolet 179 SXFT-IR spectrophotometer. |
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 | ||
I1 | 0.32012 (3) | 0.26835 (3) | 0.97653 (3) | 0.09612 (10) | |
N1 | 0.8990 (4) | 0.0835 (4) | 1.1479 (3) | 0.0958 (12) | |
N2 | 0.8529 (4) | 0.5409 (3) | 0.3573 (3) | 0.0869 (10) | |
O1 | 0.8223 (4) | −0.0984 (3) | 0.5422 (3) | 0.1048 (11) | |
C1 | 1.0574 (5) | 0.0737 (4) | 1.1539 (4) | 0.0904 (13) | |
H1A | 1.0515 | 0.1501 | 1.1950 | 0.136* | |
H1B | 1.1104 | 0.0723 | 1.0720 | 0.136* | |
H1C | 1.1171 | −0.0079 | 1.1987 | 0.136* | |
C2 | 0.8401 (5) | 0.0056 (5) | 1.2351 (4) | 0.1074 (16) | |
H2A | 0.7557 | 0.0646 | 1.2913 | 0.161* | |
H2B | 0.9263 | −0.0559 | 1.2799 | 0.161* | |
H2C | 0.7987 | −0.0446 | 1.1930 | 0.161* | |
C3 | 0.7987 (4) | 0.1759 (4) | 1.0673 (3) | 0.0702 (10) | |
C4 | 0.8456 (4) | 0.2650 (4) | 0.9901 (3) | 0.0738 (11) | |
H4 | 0.9454 | 0.2665 | 0.9945 | 0.089* | |
C5 | 0.7459 (4) | 0.3507 (3) | 0.9074 (3) | 0.0684 (10) | |
H5 | 0.7815 | 0.4085 | 0.8571 | 0.082* | |
C6 | 0.5961 (4) | 0.3555 (3) | 0.8951 (3) | 0.0602 (9) | |
C7 | 0.5481 (4) | 0.2733 (3) | 0.9733 (3) | 0.0662 (9) | |
C8 | 0.6438 (4) | 0.1837 (4) | 1.0578 (3) | 0.0703 (10) | |
H8 | 0.6049 | 0.1284 | 1.1087 | 0.084* | |
C9 | 0.4930 (4) | 0.4572 (4) | 0.8025 (3) | 0.0698 (10) | |
H9A | 0.4140 | 0.4266 | 0.7823 | 0.084* | |
H9B | 0.4348 | 0.5434 | 0.8411 | 0.084* | |
C10 | 0.5877 (4) | 0.4775 (3) | 0.6851 (3) | 0.0622 (9) | |
C11 | 0.6601 (4) | 0.3758 (3) | 0.5967 (3) | 0.0600 (9) | |
C12 | 0.7471 (4) | 0.3991 (3) | 0.4904 (3) | 0.0629 (9) | |
H12 | 0.7926 | 0.3323 | 0.4325 | 0.075* | |
C13 | 0.7693 (4) | 0.5182 (3) | 0.4666 (3) | 0.0642 (9) | |
C14 | 0.7001 (4) | 0.6166 (3) | 0.5554 (3) | 0.0689 (10) | |
H14 | 0.7136 | 0.6971 | 0.5435 | 0.083* | |
C15 | 0.6120 (4) | 0.5944 (3) | 0.6606 (3) | 0.0676 (10) | |
H15 | 0.5667 | 0.6618 | 0.7179 | 0.081* | |
C16 | 0.8916 (4) | 0.6558 (4) | 0.3420 (4) | 0.0800 (12) | |
H16A | 0.7946 | 0.7364 | 0.3546 | 0.120* | |
H16B | 0.9430 | 0.6590 | 0.2602 | 0.120* | |
H16C | 0.9632 | 0.6493 | 0.4009 | 0.120* | |
C17 | 0.9421 (5) | 0.4316 (4) | 0.2774 (4) | 0.0879 (13) | |
H17A | 1.0231 | 0.3609 | 0.3204 | 0.132* | |
H17B | 0.9929 | 0.4629 | 0.2066 | 0.132* | |
H17C | 0.8704 | 0.3976 | 0.2515 | 0.132* | |
C18 | 0.6433 (4) | 0.2480 (3) | 0.6166 (3) | 0.0639 (9) | |
H18 | 0.5523 | 0.2492 | 0.6665 | 0.077* | |
C19 | 0.7429 (4) | 0.1313 (3) | 0.5716 (3) | 0.0692 (10) | |
H19 | 0.8352 | 0.1294 | 0.5232 | 0.083* | |
C20 | 0.7237 (5) | 0.0044 (4) | 0.5898 (3) | 0.0754 (11) | |
C21 | 0.5803 (5) | −0.0020 (4) | 0.6708 (5) | 0.1036 (15) | |
H21A | 0.5956 | −0.0946 | 0.6856 | 0.155* | |
H21B | 0.4846 | 0.0463 | 0.6305 | 0.155* | |
H21C | 0.5694 | 0.0383 | 0.7477 | 0.155* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.07575 (13) | 0.1258 (2) | 0.0981 (2) | −0.05593 (12) | −0.00825 (13) | 0.01221 (15) |
N1 | 0.0807 (18) | 0.107 (2) | 0.091 (2) | −0.0339 (17) | −0.0151 (17) | 0.0260 (19) |
N2 | 0.106 (2) | 0.0722 (17) | 0.077 (2) | −0.0377 (15) | 0.0179 (17) | −0.0105 (15) |
O1 | 0.130 (2) | 0.0638 (14) | 0.107 (2) | −0.0330 (15) | 0.0177 (18) | −0.0155 (14) |
C1 | 0.085 (2) | 0.082 (2) | 0.097 (3) | −0.026 (2) | −0.024 (2) | 0.006 (2) |
C2 | 0.100 (3) | 0.119 (3) | 0.093 (3) | −0.040 (2) | −0.019 (2) | 0.036 (2) |
C3 | 0.0695 (18) | 0.0708 (19) | 0.065 (2) | −0.0252 (16) | −0.0001 (16) | −0.0033 (16) |
C4 | 0.0621 (17) | 0.085 (2) | 0.074 (2) | −0.0310 (16) | −0.0040 (16) | 0.0037 (18) |
C5 | 0.0652 (17) | 0.0677 (18) | 0.071 (2) | −0.0291 (14) | 0.0018 (16) | 0.0007 (16) |
C6 | 0.0567 (15) | 0.0603 (16) | 0.0592 (18) | −0.0210 (13) | 0.0037 (14) | −0.0099 (14) |
C7 | 0.0625 (16) | 0.0672 (18) | 0.070 (2) | −0.0291 (14) | 0.0042 (16) | −0.0093 (16) |
C8 | 0.0695 (18) | 0.0707 (19) | 0.068 (2) | −0.0290 (15) | 0.0034 (16) | −0.0028 (16) |
C9 | 0.0635 (18) | 0.0659 (19) | 0.067 (2) | −0.0148 (15) | 0.0005 (16) | −0.0083 (16) |
C10 | 0.0583 (16) | 0.0587 (17) | 0.0602 (18) | −0.0136 (14) | −0.0080 (14) | −0.0045 (15) |
C11 | 0.0592 (15) | 0.0573 (16) | 0.0590 (18) | −0.0177 (13) | −0.0128 (14) | −0.0013 (14) |
C12 | 0.0656 (17) | 0.0546 (17) | 0.0595 (18) | −0.0154 (14) | −0.0037 (15) | −0.0074 (14) |
C13 | 0.0643 (17) | 0.0590 (17) | 0.0623 (19) | −0.0186 (14) | −0.0071 (15) | −0.0007 (15) |
C14 | 0.0777 (19) | 0.0542 (17) | 0.067 (2) | −0.0198 (15) | −0.0074 (17) | −0.0012 (15) |
C15 | 0.0733 (19) | 0.0548 (17) | 0.0634 (19) | −0.0139 (15) | −0.0069 (16) | −0.0080 (15) |
C16 | 0.086 (2) | 0.072 (2) | 0.077 (2) | −0.0310 (17) | 0.0000 (19) | 0.0019 (18) |
C17 | 0.096 (2) | 0.077 (2) | 0.080 (2) | −0.0302 (19) | 0.014 (2) | −0.011 (2) |
C18 | 0.0689 (17) | 0.0618 (17) | 0.0591 (18) | −0.0241 (14) | −0.0089 (15) | −0.0025 (15) |
C19 | 0.0767 (19) | 0.0613 (18) | 0.064 (2) | −0.0235 (15) | −0.0041 (16) | −0.0017 (16) |
C20 | 0.091 (2) | 0.0613 (19) | 0.070 (2) | −0.0273 (17) | −0.0056 (18) | −0.0046 (17) |
C21 | 0.093 (3) | 0.0831 (12) | 0.072 (4) | −0.031 (12) | 0.0011 (13) | −0.0038 (12) |
I1—C7 | 2.108 (4) | C9—H9B | 0.9700 |
N1—C3 | 1.390 (5) | C10—C15 | 1.378 (5) |
N1—C2 | 1.421 (6) | C10—C11 | 1.420 (4) |
N1—C1 | 1.422 (5) | C11—C12 | 1.387 (5) |
N2—C13 | 1.393 (4) | C11—C18 | 1.456 (5) |
N2—C16 | 1.425 (5) | C12—C13 | 1.390 (5) |
N2—C17 | 1.428 (5) | C12—H12 | 0.9300 |
O1—C20 | 1.217 (4) | C13—C14 | 1.398 (5) |
C1—H1A | 0.9600 | C14—C15 | 1.379 (5) |
C1—H1B | 0.9600 | C14—H14 | 0.9300 |
C1—H1C | 0.9600 | C15—H15 | 0.9300 |
C2—H2A | 0.9600 | C16—H16A | 0.9600 |
C2—H2B | 0.9600 | C16—H16B | 0.9600 |
C2—H2C | 0.9600 | C16—H16C | 0.9600 |
C3—C4 | 1.392 (5) | C17—H17A | 0.9600 |
C3—C8 | 1.405 (5) | C17—H17B | 0.9600 |
C4—C5 | 1.377 (5) | C17—H17C | 0.9600 |
C4—H4 | 0.9300 | C18—C19 | 1.311 (4) |
C5—C6 | 1.377 (5) | C18—H18 | 0.9300 |
C5—H5 | 0.9300 | C19—C20 | 1.456 (5) |
C6—C7 | 1.347 (5) | C19—H19 | 0.9300 |
C6—C9 | 1.530 (4) | C20—C21 | 1.507 (6) |
C7—C8 | 1.389 (5) | C21—H21A | 0.9600 |
C8—H8 | 0.9300 | C21—H21B | 0.9600 |
C9—C10 | 1.506 (5) | C21—H21C | 0.9600 |
C9—H9A | 0.9700 | ||
C3—N1—C2 | 120.6 (4) | C11—C10—C9 | 121.6 (3) |
C3—N1—C1 | 121.1 (4) | C12—C11—C10 | 119.4 (3) |
C2—N1—C1 | 118.0 (3) | C12—C11—C18 | 120.0 (3) |
C13—N2—C16 | 120.3 (3) | C10—C11—C18 | 120.6 (3) |
C13—N2—C17 | 119.3 (3) | C11—C12—C13 | 122.7 (3) |
C16—N2—C17 | 117.6 (3) | C11—C12—H12 | 118.6 |
N1—C1—H1A | 109.5 | C13—C12—H12 | 118.6 |
N1—C1—H1B | 109.5 | C12—C13—N2 | 121.6 (3) |
H1A—C1—H1B | 109.5 | C12—C13—C14 | 117.4 (3) |
N1—C1—H1C | 109.5 | N2—C13—C14 | 121.0 (3) |
H1A—C1—H1C | 109.5 | C15—C14—C13 | 120.1 (3) |
H1B—C1—H1C | 109.5 | C15—C14—H14 | 120.0 |
N1—C2—H2A | 109.5 | C13—C14—H14 | 120.0 |
N1—C2—H2B | 109.5 | C10—C15—C14 | 123.3 (3) |
H2A—C2—H2B | 109.5 | C10—C15—H15 | 118.3 |
N1—C2—H2C | 109.5 | C14—C15—H15 | 118.3 |
H2A—C2—H2C | 109.5 | N2—C16—H16A | 109.5 |
H2B—C2—H2C | 109.5 | N2—C16—H16B | 109.5 |
N1—C3—C4 | 122.5 (3) | H16A—C16—H16B | 109.5 |
N1—C3—C8 | 121.7 (3) | N2—C16—H16C | 109.5 |
C4—C3—C8 | 115.9 (3) | H16A—C16—H16C | 109.5 |
C5—C4—C3 | 120.8 (4) | H16B—C16—H16C | 109.5 |
C5—C4—H4 | 119.6 | N2—C17—H17A | 109.5 |
C3—C4—H4 | 119.6 | N2—C17—H17B | 109.5 |
C4—C5—C6 | 123.4 (3) | H17A—C17—H17B | 109.5 |
C4—C5—H5 | 118.3 | N2—C17—H17C | 109.5 |
C6—C5—H5 | 118.3 | H17A—C17—H17C | 109.5 |
C7—C6—C5 | 115.7 (3) | H17B—C17—H17C | 109.5 |
C7—C6—C9 | 124.9 (3) | C19—C18—C11 | 126.9 (3) |
C5—C6—C9 | 119.3 (3) | C19—C18—H18 | 116.5 |
C6—C7—C8 | 123.4 (3) | C11—C18—H18 | 116.5 |
C6—C7—I1 | 122.6 (2) | C18—C19—C20 | 126.7 (3) |
C8—C7—I1 | 114.0 (3) | C18—C19—H19 | 116.7 |
C7—C8—C3 | 120.7 (3) | C20—C19—H19 | 116.7 |
C7—C8—H8 | 119.7 | O1—C20—C19 | 121.6 (4) |
C3—C8—H8 | 119.7 | O1—C20—C21 | 118.5 (4) |
C10—C9—C6 | 114.1 (3) | C19—C20—C21 | 119.9 (3) |
C10—C9—H9A | 108.7 | C20—C21—H21A | 109.5 |
C6—C9—H9A | 108.7 | C20—C21—H21B | 109.5 |
C10—C9—H9B | 108.7 | H21A—C21—H21B | 109.5 |
C6—C9—H9B | 108.7 | C20—C21—H21C | 109.5 |
H9A—C9—H9B | 107.6 | H21A—C21—H21C | 109.5 |
C15—C10—C11 | 117.1 (3) | H21B—C21—H21C | 109.5 |
C15—C10—C9 | 121.3 (3) |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register