Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806023269/is2057sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806023269/is2057Isup2.hkl |
CCDC reference: 613741
Key indicators
- Single-crystal X-ray study
- T = 203 K
- Mean (C-C) = 0.012 Å
- R factor = 0.053
- wR factor = 0.125
- Data-to-parameter ratio = 20.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 12
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 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 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrystalClear (Rigaku, 2001); cell refinement: CrystalClear; data reduction: TEXSAN (Molecular Structure Corporation, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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.
[InBr3(C12H13N3)] | F(000) = 1040 |
Mr = 553.80 | Dx = 2.319 Mg m−3 |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 5462 reflections |
a = 13.995 (2) Å | θ = 4.1–27.5° |
b = 14.227 (2) Å | µ = 9.04 mm−1 |
c = 7.9682 (12) Å | T = 203 K |
V = 1586.6 (4) Å3 | Plate, colorless |
Z = 4 | 0.12 × 0.06 × 0.02 mm |
Rigaku/MSC Mercury CCD diffractometer | 1802 reflections with I > 2σ(I) |
Detector resolution: 14.6199 pixels mm-1 | Rint = 0.056 |
ω scans | θmax = 27.5°, θmin = 4.1° |
Absorption correction: multi-scan (Jacobson, 1998) | h = −15→18 |
Tmin = 0.410, Tmax = 0.840 | k = −18→16 |
14768 measured reflections | l = −10→10 |
1877 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.053 | w = 1/[σ2(Fo2) + (0.05P)2 + 3P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.125 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.84 e Å−3 |
1877 reflections | Δρmin = −0.69 e Å−3 |
93 parameters |
Experimental. 1H NMR (400 MHz, DMSO-d6): δ 4.16 (d, J = 16.8 Hz, 2H, CH2), 4.64 (d, J = 16.8 Hz, 1H, CH2), 4.66 (d, J = 16.8 Hz, 1H, CH2), 6.42 (s, 1H, NH), 7.50 (br, 2H, py), 7.55 (br, 2H, py), 7.97 (br, 2H, py), 8.88 (br, 2H, py); 13C NMR (100.4 MHz, DMSO-d6): δ 51.32 (s, CH2), 124.61 (s, 2 C, CH), 140.55 (s, CH), 144.72 (s, CH), 151.69 (s, ipso-C); elemental analysis found: C 25.65, H 2.22, N 7.16%; calculated for C12H13Br3InN3: C 26.03, H 2.37, N 7.59%. |
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 | ||
In1 | 0.87159 (5) | 0.2500 | 0.70375 (9) | 0.01798 (19) | |
Br1 | 1.01642 (8) | 0.2500 | 0.90168 (14) | 0.0305 (3) | |
Br2 | 0.77399 (6) | 0.38912 (6) | 0.82974 (10) | 0.0291 (2) | |
N1 | 0.7668 (6) | 0.2500 | 0.4769 (11) | 0.0201 (17) | |
H1N | 0.707 (9) | 0.2500 | 0.521 (16) | 0.024* | |
N2 | 0.9383 (4) | 0.1506 (4) | 0.5066 (8) | 0.0203 (12) | |
C1 | 0.7813 (5) | 0.1617 (5) | 0.3776 (10) | 0.0261 (16) | |
H1A | 0.7429 | 0.1112 | 0.4272 | 0.031* | |
H1B | 0.7587 | 0.1718 | 0.2626 | 0.031* | |
C2 | 0.8837 (5) | 0.1319 (5) | 0.3730 (9) | 0.0224 (15) | |
C3 | 0.9204 (7) | 0.0843 (6) | 0.2343 (11) | 0.0319 (18) | |
H3A | 0.8814 | 0.0713 | 0.1410 | 0.038* | |
C4 | 1.0142 (7) | 0.0567 (6) | 0.2364 (10) | 0.0321 (18) | |
H4A | 1.0399 | 0.0245 | 0.1438 | 0.038* | |
C5 | 1.0710 (6) | 0.0760 (5) | 0.3734 (10) | 0.0268 (16) | |
H5A | 1.1352 | 0.0567 | 0.3766 | 0.032* | |
C6 | 1.0304 (5) | 0.1248 (5) | 0.5068 (10) | 0.0227 (15) | |
H6A | 1.0687 | 0.1401 | 0.5998 | 0.027* |
U11 | U22 | U33 | U12 | U13 | U23 | |
In1 | 0.0137 (3) | 0.0230 (3) | 0.0172 (3) | 0.000 | 0.0003 (3) | 0.000 |
Br1 | 0.0205 (6) | 0.0476 (7) | 0.0234 (6) | 0.000 | −0.0061 (4) | 0.000 |
Br2 | 0.0218 (4) | 0.0328 (4) | 0.0326 (4) | 0.0034 (3) | 0.0039 (3) | −0.0083 (3) |
N1 | 0.013 (4) | 0.023 (4) | 0.024 (4) | 0.000 | 0.001 (3) | 0.000 |
N2 | 0.021 (3) | 0.019 (3) | 0.021 (3) | −0.003 (2) | 0.002 (2) | 0.003 (2) |
C1 | 0.019 (4) | 0.027 (4) | 0.032 (4) | −0.005 (3) | −0.009 (3) | −0.005 (3) |
C2 | 0.021 (4) | 0.024 (3) | 0.022 (3) | 0.000 (3) | −0.004 (3) | 0.005 (3) |
C3 | 0.039 (5) | 0.032 (4) | 0.024 (4) | 0.002 (4) | −0.003 (3) | −0.006 (3) |
C4 | 0.043 (5) | 0.034 (4) | 0.019 (4) | −0.001 (4) | 0.009 (3) | −0.004 (3) |
C5 | 0.021 (4) | 0.027 (4) | 0.032 (4) | 0.001 (3) | 0.005 (3) | 0.000 (3) |
C6 | 0.017 (3) | 0.024 (4) | 0.027 (4) | −0.001 (3) | −0.002 (3) | 0.003 (3) |
In1—N1 | 2.328 (9) | C1—C2 | 1.496 (10) |
In1—N2 | 2.311 (6) | C1—H1A | 0.9800 |
In1—N2i | 2.311 (6) | C1—H1B | 0.9800 |
In1—Br1 | 2.5682 (13) | C2—C3 | 1.394 (11) |
In1—Br2 | 2.6060 (9) | C3—C4 | 1.370 (13) |
In1—Br2i | 2.6060 (9) | C3—H3A | 0.9400 |
N1—C1i | 1.498 (9) | C4—C5 | 1.378 (12) |
N1—C1 | 1.498 (9) | C4—H4A | 0.9400 |
N1—H1N | 0.91 (13) | C5—C6 | 1.391 (11) |
N2—C2 | 1.336 (9) | C5—H5A | 0.9400 |
N2—C6 | 1.341 (9) | C6—H6A | 0.9400 |
N1—In1—N2 | 74.1 (2) | C6—N2—In1 | 123.7 (5) |
N2—In1—N2i | 75.5 (3) | C2—C1—N1 | 112.4 (6) |
N2i—In1—N1 | 74.1 (2) | C2—C1—H1A | 109.1 |
N2—In1—Br1 | 95.67 (16) | N1—C1—H1A | 109.1 |
N2i—In1—Br1 | 95.67 (16) | C2—C1—H1B | 109.1 |
N1—In1—Br1 | 166.9 (2) | N1—C1—H1B | 109.1 |
N2—In1—Br2 | 159.80 (16) | H1A—C1—H1B | 107.9 |
N2i—In1—Br2 | 90.49 (14) | N2—C2—C3 | 121.2 (7) |
N1—In1—Br2 | 88.21 (14) | N2—C2—C1 | 118.1 (7) |
Br1—In1—Br2 | 100.20 (3) | C3—C2—C1 | 120.7 (7) |
N2—In1—Br2i | 90.49 (14) | C4—C3—C2 | 118.8 (8) |
N2i—In1—Br2i | 159.80 (16) | C4—C3—H3A | 120.6 |
N1—In1—Br2i | 88.21 (14) | C2—C3—H3A | 120.6 |
Br1—In1—Br2i | 100.20 (3) | C3—C4—C5 | 120.4 (8) |
Br2—In1—Br2i | 98.84 (4) | C3—C4—H4A | 119.8 |
C1i—N1—C1 | 113.9 (9) | C5—C4—H4A | 119.8 |
C1i—N1—In1 | 108.9 (5) | C4—C5—C6 | 118.0 (7) |
C1—N1—In1 | 108.9 (5) | C4—C5—H5A | 121.0 |
C1i—N1—H1N | 109 (4) | C6—C5—H5A | 121.0 |
C1—N1—H1N | 109 (4) | N2—C6—C5 | 121.9 (7) |
In1—N1—H1N | 106 (8) | N2—C6—H6A | 119.1 |
C2—N2—C6 | 119.7 (7) | C5—C6—H6A | 119.1 |
C2—N2—In1 | 115.6 (5) | ||
N2—In1—N1—C1i | −101.9 (6) | Br2—In1—N2—C6 | 131.6 (5) |
N2i—In1—N1—C1i | −22.9 (5) | Br2i—In1—N2—C6 | −110.5 (5) |
Br1—In1—N1—C1i | −62.4 (5) | C1i—N1—C1—C2 | 85.9 (9) |
Br2—In1—N1—C1i | 68.1 (5) | In1—N1—C1—C2 | −35.9 (8) |
Br2i—In1—N1—C1i | 167.0 (5) | C6—N2—C2—C3 | 1.3 (11) |
N2—In1—N1—C1 | 22.9 (5) | In1—N2—C2—C3 | 170.7 (6) |
N2i—In1—N1—C1 | 101.9 (6) | C6—N2—C2—C1 | 179.9 (6) |
Br1—In1—N1—C1 | 62.4 (5) | In1—N2—C2—C1 | −10.7 (8) |
Br2—In1—N1—C1 | −167.0 (5) | N1—C1—C2—N2 | 32.4 (10) |
Br2i—In1—N1—C1 | −68.1 (5) | N1—C1—C2—C3 | −149.0 (7) |
N2i—In1—N2—C2 | −84.6 (5) | N2—C2—C3—C4 | −0.2 (12) |
N1—In1—N2—C2 | −7.4 (5) | C1—C2—C3—C4 | −178.8 (8) |
Br1—In1—N2—C2 | −179.1 (5) | C2—C3—C4—C5 | 0.0 (13) |
Br2—In1—N2—C2 | −37.3 (8) | C3—C4—C5—C6 | −0.7 (12) |
Br2i—In1—N2—C2 | 80.6 (5) | C2—N2—C6—C5 | −2.1 (11) |
N2i—In1—N2—C6 | 84.3 (6) | In1—N2—C6—C5 | −170.6 (5) |
N1—In1—N2—C6 | 161.5 (6) | C4—C5—C6—N2 | 1.9 (11) |
Br1—In1—N2—C6 | −10.2 (6) |
Symmetry code: (i) x, −y+1/2, z. |