Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680100722X/ob6039sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680100722X/ob6039Isup2.hkl |
CCDC reference: 170292
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.006 Å
- R factor = 0.050
- wR factor = 0.136
- Data-to-parameter ratio = 19.1
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
DIFMN_02 Alert C The minimum difference density is < -0.1*ZMAX*0.75 _refine_diff_density_min given = -4.105 Test value = -3.975 DIFMN_03 Alert C The minimum difference density is < -0.1*ZMAX*0.75 The relevant atom site should be identified. RINTA_01 Alert C The value of Rint is greater than 0.10 Rint given 0.105
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check
Data collection: DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997).
C7H5I2NO3 | F(000) = 736 |
Mr = 404.92 | Dx = 2.658 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.5577 (2) Å | Cell parameters from 2295 reflections |
b = 10.7752 (3) Å | θ = 2.7–27.5° |
c = 11.0632 (3) Å | µ = 6.19 mm−1 |
β = 97.3860 (9)° | T = 150 K |
V = 1011.68 (5) Å3 | Lozenge, colourless |
Z = 4 | 0.40 × 0.10 × 0.05 mm |
Enraf-Nonius KappaCCD area-detector diffractometer | 2295 independent reflections |
Radiation source: Enraf-Nonius FR591 rotating-anode | 2145 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.106 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 2.7° |
φ and ω scans to fill Ewald sphere | h = −11→11 |
Absorption correction: multi-scan using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995) | k = −13→13 |
Tmin = 0.191, Tmax = 0.747 | l = −13→14 |
8844 measured reflections |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.136 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0986P)2 + 0.3356P] where P = (Fo2 + 2Fc2)/3 |
2295 reflections | (Δ/σ)max = 0.001 |
120 parameters | Δρmax = 1.29 e Å−3 |
0 restraints | Δρmin = −4.11 e Å−3 |
Experimental. Please note cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. |
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 | 1.17472 (4) | 0.09424 (3) | −0.09697 (3) | 0.02768 (18) | |
I2 | 1.08528 (3) | 0.47217 (3) | 0.29897 (3) | 0.02279 (18) | |
O1 | 1.2523 (4) | 0.2722 (3) | 0.1428 (3) | 0.0238 (7) | |
O2 | 0.5283 (4) | 0.2825 (3) | 0.0559 (3) | 0.0257 (7) | |
H2' | 0.4446 | 0.2819 | 0.0880 | 0.026 (7)* | |
O3 | 0.3844 (4) | 0.3885 (4) | −0.0926 (4) | 0.0307 (8) | |
N1 | 0.8087 (4) | 0.3449 (3) | −0.0295 (3) | 0.0198 (8) | |
C1 | 0.6585 (5) | 0.3827 (5) | −0.0976 (4) | 0.0219 (9) | |
H1A | 0.6505 | 0.3445 | −0.1795 | 0.026 (7)* | |
H1B | 0.6610 | 0.4738 | −0.1089 | 0.026 (7)* | |
C2 | 0.8607 (6) | 0.4027 (4) | 0.0776 (4) | 0.0199 (9) | |
H2 | 0.7949 | 0.4613 | 0.1107 | 0.026 (7)* | |
C3 | 1.0062 (5) | 0.3771 (4) | 0.1376 (4) | 0.0187 (8) | |
C4 | 1.1152 (5) | 0.2911 (4) | 0.0912 (4) | 0.0192 (9) | |
C5 | 1.0465 (5) | 0.2307 (4) | −0.0192 (4) | 0.0197 (9) | |
C6 | 0.9003 (5) | 0.2603 (5) | −0.0767 (4) | 0.0213 (9) | |
H6 | 0.8624 | 0.2206 | −0.1514 | 0.026 (7)* | |
C7 | 0.5088 (6) | 0.3506 (4) | −0.0426 (5) | 0.0217 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0233 (3) | 0.0360 (3) | 0.0238 (3) | 0.00914 (11) | 0.00323 (17) | −0.00365 (12) |
I2 | 0.0179 (3) | 0.0314 (3) | 0.0186 (2) | −0.00322 (10) | 0.00060 (16) | −0.00359 (11) |
O1 | 0.0127 (14) | 0.0398 (18) | 0.0187 (15) | 0.0021 (13) | 0.0007 (12) | 0.0007 (14) |
O2 | 0.0133 (15) | 0.040 (2) | 0.0236 (16) | 0.0010 (13) | 0.0027 (13) | 0.0024 (15) |
O3 | 0.0154 (16) | 0.0390 (19) | 0.036 (2) | 0.0047 (14) | −0.0028 (15) | 0.0045 (16) |
N1 | 0.0122 (17) | 0.0269 (19) | 0.0196 (19) | 0.0010 (14) | −0.0012 (15) | −0.0006 (15) |
C1 | 0.012 (2) | 0.036 (2) | 0.017 (2) | 0.0027 (17) | 0.0012 (17) | −0.0018 (18) |
C2 | 0.015 (2) | 0.029 (2) | 0.017 (2) | −0.0001 (16) | 0.0047 (17) | 0.0005 (17) |
C3 | 0.016 (2) | 0.024 (2) | 0.016 (2) | −0.0021 (17) | −0.0011 (16) | 0.0005 (17) |
C4 | 0.014 (2) | 0.029 (2) | 0.0144 (19) | −0.0027 (17) | 0.0006 (17) | 0.0038 (17) |
C5 | 0.016 (2) | 0.028 (2) | 0.0161 (19) | 0.0015 (16) | 0.0054 (17) | −0.0016 (17) |
C6 | 0.0115 (19) | 0.030 (2) | 0.022 (2) | −0.0036 (17) | 0.0012 (17) | −0.0014 (19) |
C7 | 0.019 (2) | 0.026 (2) | 0.020 (2) | 0.0016 (18) | 0.0016 (17) | −0.0008 (17) |
I1—C5 | 2.085 (4) | C1—C7 | 1.526 (7) |
I2—C3 | 2.094 (4) | C1—H1A | 0.9900 |
O1—C4 | 1.253 (5) | C1—H1B | 0.9900 |
O2—C7 | 1.305 (6) | C2—C3 | 1.362 (7) |
O2—H2' | 0.8400 | C2—H2 | 0.9500 |
O3—C7 | 1.206 (6) | C3—C4 | 1.455 (7) |
N1—C6 | 1.350 (6) | C4—C5 | 1.441 (6) |
N1—C2 | 1.361 (6) | C5—C6 | 1.366 (6) |
N1—C1 | 1.462 (5) | C6—H6 | 0.9500 |
C7—O2—H2' | 109.5 | C2—C3—I2 | 119.5 (4) |
C6—N1—C2 | 120.3 (4) | C4—C3—I2 | 117.5 (3) |
C6—N1—C1 | 120.3 (4) | O1—C4—C5 | 124.7 (4) |
C2—N1—C1 | 119.2 (4) | O1—C4—C3 | 123.2 (4) |
N1—C1—C7 | 117.3 (4) | C5—C4—C3 | 112.1 (4) |
N1—C1—H1A | 108.0 | C6—C5—C4 | 122.6 (4) |
C7—C1—H1A | 108.0 | C6—C5—I1 | 118.1 (3) |
N1—C1—H1B | 108.0 | C4—C5—I1 | 119.3 (3) |
C7—C1—H1B | 108.0 | N1—C6—C5 | 121.3 (4) |
H1A—C1—H1B | 107.2 | N1—C6—H6 | 119.3 |
N1—C2—C3 | 120.5 (4) | C5—C6—H6 | 119.3 |
N1—C2—H2 | 119.7 | O3—C7—O2 | 125.7 (5) |
C3—C2—H2 | 119.7 | O3—C7—C1 | 118.4 (4) |
C2—C3—C4 | 123.0 (4) | O2—C7—C1 | 115.9 (4) |
C6—N1—C1—C7 | 115.3 (5) | O1—C4—C5—C6 | −175.5 (5) |
C2—N1—C1—C7 | −69.5 (6) | C3—C4—C5—C6 | 5.0 (6) |
C6—N1—C2—C3 | 0.9 (7) | O1—C4—C5—I1 | 3.6 (6) |
C1—N1—C2—C3 | −174.3 (4) | C3—C4—C5—I1 | −176.0 (3) |
N1—C2—C3—C4 | 1.7 (7) | C2—N1—C6—C5 | −0.2 (7) |
N1—C2—C3—I2 | 177.9 (3) | C1—N1—C6—C5 | 174.9 (4) |
C2—C3—C4—O1 | 176.1 (4) | C4—C5—C6—N1 | −3.0 (7) |
I2—C3—C4—O1 | −0.2 (6) | I1—C5—C6—N1 | 177.9 (3) |
C2—C3—C4—C5 | −4.4 (6) | N1—C1—C7—O3 | 174.8 (4) |
I2—C3—C4—C5 | 179.3 (3) | N1—C1—C7—O2 | −5.7 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2′···O1i | 0.84 | 1.83 | 2.665 (5) | 174 |
C1—H1A···O1ii | 0.99 | 2.58 | 3.503 (6) | 156 |
C2—H2···O3iii | 0.95 | 2.22 | 3.095 (6) | 152 |
C6—H6···O1ii | 0.95 | 2.35 | 3.217 (6) | 151 |
Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+1, −y+1, −z. |