4,5-Dichlorophthalic anhydride (CPA) lies on a twofold axis in space group
C2/
c; the molecules pack as stacks of two-dimensional sheets. Polymorph A of 5,6-dichlorobenzfurazan 1-oxide (CBF; systematic name 5,6-dichloro-2,1,3-benzoxadiazole 1-oxide) is isomorphous with CPA with disordered CBF molecules being pseudo-isosteric with the CPA molecule. Polymorph C of CBF has similar unit-cell dimensions but the arrangement of the molecules in the cell is different. 4,5-Dibromophthalic anhydride occurs in space group
P1 in a structure derived from the CPA structure. The four structures all have similar two-dimensional sheets of molecules, but differ, in addition to the disorder of the CBF molecules, in the stacking of successive sheets. There are three polymorphs of 5,6-dichlorobenzfurazan 1-oxide. In all three the molecules are disordered about twofold or pseudo-twofold axes. In all three the molecules form chains involving similar Cl
O contacts along the direction of the twofold axis. In polymorphs A and C these chains form virtually identical two-dimensional sheets with inter-chain C—H
O, C—H
N and Cl
Cl contacts, but with different stacking arrangements between the sheets. In polymorph B the chains are associated in face-to-face pairs with the same face-to-face overlap as in A, at an average distance of 3.42 Å compared to an average distance of 3.38 Å in A (
cf. Table 8); there are no two-dimensional sheets.
Supporting information
| Crystallographic Information File (CIF) Contains datablocks Alt, Art, Blt, Brt, Clt, Crt, CPA, BPA, global |
| Structure factor file (CIF format) Contains datablock 15110 |
| Structure factor file (CIF format) Contains datablock 15130b |
| Structure factor file (CIF format) Contains datablock 15113 |
| Structure factor file (CIF format) Contains datablock 15112 |
| Structure factor file (CIF format) Contains datablock 15221 |
| Structure factor file (CIF format) Contains datablock 15220b |
| Structure factor file (CIF format) Contains datablock 15166a |
| Structure factor file (CIF format) Contains datablock 15164a |
CCDC references: 134753; 134754; 134755; 134756; 134757; 134758; 134759; 134760
(Alt) 5,6-dichlorobenzfurazan-1-oxide
top
Crystal data top
C6H2Cl2N2O2 | F(000) = 408 |
Mr = 205.00 | Dx = 1.872 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.397 (2) Å | Cell parameters from 25 reflections |
b = 8.871 (2) Å | θ = 11–22° |
c = 7.222 (4) Å | µ = 0.84 mm−1 |
β = 95.12 (3)° | T = 173 K |
V = 727.3 (5) Å3 | Sword-shaped, yellow |
Z = 4 | 0.50 × 0.28 × 0.12 mm |
Data collection top
CAD-4 diffractometer | 1140 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.026 |
Graphite monochromator | θmax = 32°, θmin = 2.9° |
ω–2θ scans | h = −16→16 |
Absorption correction: psi scan North, A. C. T., Phillips, D. C., and Mathews, F. S. (1968).
Acta Cryst., A24, 351-359. | k = 0→13 |
Tmin = 0.74, Tmax = 0.90 | l = −10→10 |
2528 measured reflections | 3 standard reflections every 50 min |
1267 independent reflections | intensity decay: <1% |
Refinement top
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)] = 0.029 | Idealized positions |
wR(F2) = 0.076 | Calculated w = 1/[σ2(Fo2) + (0.029P)2 + 0.14P] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max = 0.01 |
1267 reflections | Δρmax = 0.47 e Å−3 |
110 parameters | Δρmin = −0.35 e Å−3 |
33 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.039 (3) |
Crystal data top
C6H2Cl2N2O2 | V = 727.3 (5) Å3 |
Mr = 205.00 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 11.397 (2) Å | µ = 0.84 mm−1 |
b = 8.871 (2) Å | T = 173 K |
c = 7.222 (4) Å | 0.50 × 0.28 × 0.12 mm |
β = 95.12 (3)° | |
Data collection top
CAD-4 diffractometer | 1140 reflections with I > 2σ(I) |
Absorption correction: psi scan North, A. C. T., Phillips, D. C., and Mathews, F. S. (1968).
Acta Cryst., A24, 351-359. | Rint = 0.026 |
Tmin = 0.74, Tmax = 0.90 | 3 standard reflections every 50 min |
2528 measured reflections | intensity decay: <1% |
1267 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.029 | 33 restraints |
wR(F2) = 0.076 | Idealized positions |
S = 1.13 | Δρmax = 0.47 e Å−3 |
1267 reflections | Δρmin = −0.35 e Å−3 |
110 parameters | |
Special details top
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 on F2 for ALL reflections except for 0 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.5438 (5) | 0.2394 (5) | 0.2850 (10) | 0.0196 (6) | 0.50 |
C2 | 0.4298 (4) | 0.2469 (5) | 0.1901 (10) | 0.0216 (7) | 0.50 |
C3 | 0.3798 (7) | 0.3893 (12) | 0.1527 (12) | 0.0227 (9) | 0.50 |
H3 | 0.3044 | 0.3974 | 0.0910 | 0.027* | 0.50 |
C4 | 0.4430 (9) | 0.5146 (12) | 0.2069 (15) | 0.0202 (8) | 0.50 |
C5 | 0.5623 (8) | 0.5003 (12) | 0.2997 (14) | 0.0209 (8) | 0.50 |
C6 | 0.6137 (7) | 0.3655 (11) | 0.3403 (12) | 0.0238 (10) | 0.50 |
H6 | 0.6890 | 0.3572 | 0.3992 | 0.029* | 0.50 |
N1 | 0.5718 (2) | 0.0959 (2) | 0.3104 (3) | 0.0247 (4) | 0.50 |
N2 | 0.3874 (2) | 0.1079 (3) | 0.1540 (4) | 0.0272 (4) | 0.50 |
O1 | 0.6566 (2) | 0.0266 (2) | 0.3865 (3) | 0.0335 (4) | 0.50 |
O2 | 0.47343 (13) | 0.0101 (2) | 0.2272 (3) | 0.0299 (4) | 0.50 |
Cl4 | 0.3794 (6) | 0.6869 (7) | 0.1563 (9) | 0.0276 (5) | 0.50 |
Cl5 | 0.6330 (5) | 0.6699 (6) | 0.3490 (9) | 0.0257 (4) | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.019 (2) | 0.0157 (8) | 0.024 (2) | −0.0019 (9) | 0.0002 (13) | −0.0023 (8) |
C2 | 0.017 (2) | 0.0234 (10) | 0.024 (2) | −0.0013 (9) | −0.0006 (13) | −0.0022 (9) |
C3 | 0.0253 (11) | 0.015 (3) | 0.0282 (11) | 0.0038 (11) | 0.0041 (9) | −0.0001 (11) |
C4 | 0.0220 (11) | 0.016 (2) | 0.0229 (11) | −0.0069 (12) | 0.0036 (9) | −0.0041 (11) |
C5 | 0.0210 (13) | 0.018 (2) | 0.0236 (12) | −0.006 (2) | 0.0023 (10) | −0.004 (2) |
C6 | 0.0248 (13) | 0.018 (3) | 0.0286 (11) | 0.0066 (15) | 0.0032 (10) | 0.0004 (13) |
N1 | 0.0205 (9) | 0.0205 (8) | 0.0320 (10) | −0.0004 (8) | −0.0037 (8) | −0.0012 (7) |
N2 | 0.0217 (10) | 0.0227 (8) | 0.0359 (11) | −0.0016 (8) | −0.0047 (8) | −0.0035 (7) |
O1 | 0.0256 (7) | 0.0249 (8) | 0.0478 (10) | 0.0049 (6) | −0.0092 (7) | 0.0022 (7) |
O2 | 0.0233 (9) | 0.0194 (6) | 0.0458 (11) | −0.0022 (5) | −0.0037 (8) | −0.0031 (6) |
Cl4 | 0.0272 (11) | 0.0213 (11) | 0.0343 (5) | 0.0031 (7) | 0.0032 (6) | 0.0015 (6) |
Cl5 | 0.0249 (10) | 0.0186 (10) | 0.0337 (6) | −0.0029 (6) | 0.0028 (6) | −0.0052 (6) |
Geometric parameters (Å, º) top
C1—N1 | 1.321 (5) | C4—Cl4 | 1.717 (11) |
C1—C6 | 1.411 (8) | C5—C6 | 1.352 (12) |
C1—C2 | 1.415 (5) | C5—Cl5 | 1.729 (10) |
C2—N2 | 1.341 (5) | N1—O1 | 1.233 (3) |
C2—C3 | 1.402 (9) | N1—O2 | 1.441 (3) |
C3—C4 | 1.363 (12) | N2—O2 | 1.378 (3) |
C4—C5 | 1.467 (4) | | |
| | | |
C1···C2i | 0.344 (5) | C6···C4i | 1.50 (2) |
C1···C1i | 1.077 (8) | N1···N2i | 0.521 (2) |
C2···C1i | 0.344 (5) | N1···O2i | 0.945 (3) |
C2···C6i | 1.176 (10) | N1···C2i | 1.339 (5) |
C2···C2i | 1.750 (6) | N1···N1i | 1.785 (5) |
C3···C6i | 0.23 (2) | N1···C1i | 1.915 (4) |
C3···C5i | 1.22 (2) | N2···N1i | 0.521 (2) |
C1···N2i | 1.452 (5) | N2···O1i | 0.912 (3) |
C1···C3i | 1.631 (9) | N2···C1i | 1.452 (5) |
C1···N1i | 1.915 (4) | O1···N2i | 0.912 (3) |
C2···N1i | 1.339 (5) | O1···O2i | 1.636 (2) |
C3···C1i | 1.631 (9) | O2···O2i | 0.663 (3) |
C4···C5i | 0.15 (2) | O2···N1i | 0.945 (3) |
C4···C4i | 1.39 (2) | O2···O1i | 1.636 (2) |
C4···C6i | 1.50 (2) | Cl4···Cl5i | 0.208 (10) |
C4···Cl5i | 1.658 (14) | Cl4···C5i | 1.801 (13) |
C5···C4i | 0.15 (2) | Cl5···Cl4i | 0.208 (9) |
C5···C3i | 1.22 (2) | Cl5···C4i | 1.658 (14) |
C5···C5i | 1.53 (2) | Cl4···Cl4ii | 3.723 |
C5···Cl4i | 1.801 (13) | Cl4···Cl5iii | 3.649 |
C6···C3i | 0.23 (2) | Cl5···Cl4iv | 3.649 |
C6···C2i | 1.176 (10) | Cl5···Cl5v | 3.585 |
| | | |
C6—C1—C2 | 124.8 (7) | C6i—C4—Cl5i | 118.2 (7) |
C3—C2—C1 | 118.4 (6) | C5i—C4—Cl4 | 123 (7) |
C4—C3—C2 | 119.0 (8) | C4i—C4—Cl4 | 117.1 (4) |
C3—C4—C5 | 120.4 (11) | C6i—C4—Cl4 | 124.9 (7) |
C6—C5—C4 | 122.8 (11) | Cl5i—C4—Cl4 | 6.8 (3) |
C5—C6—C1 | 114.7 (7) | C4i—C5—C3i | 171 (8) |
N1—C1—C2 | 108.2 (4) | C4i—C5—C6 | 174 (9) |
N2—C2—C1 | 110.5 (4) | C3i—C5—C6 | 8.2 (6) |
C1—N1—O2 | 106.3 (3) | C4i—C5—C4 | 56 (7) |
C2—N2—O2 | 105.8 (2) | C3i—C5—C4 | 131.0 (11) |
N2—O2—N1 | 109.1 (2) | C4i—C5—C5i | 61 (7) |
O1—N1—O2 | 118.2 (2) | C3i—C5—C5i | 126.0 (5) |
C5—C4—Cl4 | 122.1 (10) | C6—C5—C5i | 117.8 (5) |
C4—C5—Cl5 | 114.5 (10) | C4—C5—C5i | 5.0 (8) |
N1—C1—C6 | 127.0 (6) | C4i—C5—Cl5 | 59 (7) |
N2—C2—C3 | 131.1 (5) | C3i—C5—Cl5 | 114.5 (7) |
C3—C4—Cl4 | 117.6 (7) | C5i—C5—Cl5 | 119.5 (4) |
C6—C5—Cl5 | 122.7 (7) | C4i—C5—Cl4i | 53 (7) |
O1—N1—C1 | 135.5 (3) | C3i—C5—Cl4i | 120.7 (7) |
C2i—C1—C1i | 168.1 (18) | C6—C5—Cl4i | 128.9 (7) |
C2i—C1—N1 | 85.6 (15) | C4—C5—Cl4i | 108.3 (10) |
C1i—C1—N1 | 105.5 (2) | C5i—C5—Cl4i | 113.2 (4) |
C2i—C1—C6 | 41.5 (13) | Cl5—C5—Cl4i | 6.3 (3) |
C1i—C1—C6 | 127.5 (5) | C3i—C6—C2i | 174 (5) |
C2i—C1—C2 | 165.8 (18) | C3i—C6—C5 | 50 (5) |
C1i—C1—C2 | 2.9 (4) | C2i—C6—C5 | 125.8 (8) |
C2i—C1—N2i | 64.6 (14) | C3i—C6—C1 | 164 (5) |
C1i—C1—N2i | 126.5 (2) | C2i—C6—C1 | 11.2 (3) |
N1—C1—N2i | 20.99 (12) | C3i—C6—C4i | 50 (5) |
C6—C1—N2i | 106.0 (5) | C2i—C6—C4i | 125.6 (8) |
C2—C1—N2i | 129.2 (4) | C5—C6—C4i | 0.6 (9) |
C2i—C1—C3i | 43.6 (14) | C1—C6—C4i | 114.5 (7) |
C1i—C1—C3i | 125.4 (4) | N2i—N1—O2i | 138.2 (5) |
N1—C1—C3i | 129.1 (5) | N2i—N1—O1 | 41.7 (4) |
C6—C1—C3i | 2.2 (8) | O2i—N1—O1 | 96.5 (2) |
C2—C1—C3i | 122.7 (6) | N2i—N1—C1 | 93.8 (4) |
N2i—C1—C3i | 108.1 (5) | O2i—N1—C1 | 128.0 (3) |
C2i—C1—N1i | 149.3 (15) | N2i—N1—C2i | 79.0 (4) |
C1i—C1—N1i | 41.66 (15) | O2i—N1—C2i | 142.9 (3) |
N1—C1—N1i | 63.9 (2) | O1—N1—C2i | 120.6 (2) |
C6—C1—N1i | 169.1 (5) | C1—N1—C2i | 14.8 (2) |
C2—C1—N1i | 44.3 (2) | N2i—N1—O2 | 159.9 (5) |
N2i—C1—N1i | 84.9 (2) | O2i—N1—O2 | 21.74 (12) |
C3i—C1—N1i | 167.0 (5) | C2i—N1—O2 | 121.1 (2) |
C1i—C2—C6i | 127.3 (16) | N2i—N1—N1i | 168.2 (4) |
C1i—C2—N1i | 79.6 (14) | O2i—N1—N1i | 53.6 (2) |
C6i—C2—N1i | 152.8 (6) | O1—N1—N1i | 150.05 (14) |
C1i—C2—N2 | 102.0 (15) | C1—N1—N1i | 74.5 (2) |
C6i—C2—N2 | 130.5 (6) | C2i—N1—N1i | 89.3 (2) |
N1i—C2—N2 | 22.42 (12) | O2—N1—N1i | 31.86 (12) |
C1i—C2—C3 | 126.7 (16) | N2i—N1—C1i | 126.5 (5) |
C6i—C2—C3 | 1.0 (8) | O2i—N1—C1i | 95.3 (2) |
N1i—C2—C3 | 153.5 (5) | O1—N1—C1i | 168.1 (2) |
C1i—C2—C1 | 9.0 (14) | C1—N1—C1i | 32.8 (3) |
C6i—C2—C1 | 119.0 (7) | C2i—N1—C1i | 47.6 (2) |
N1i—C2—C1 | 88.1 (3) | O2—N1—C1i | 73.5 (2) |
C1i—C2—C2i | 11.4 (14) | N1i—N1—C1i | 41.66 (15) |
C6i—C2—C2i | 116.3 (5) | N1i—N2—O1i | 116.0 (5) |
N1i—C2—C2i | 90.7 (2) | N1i—N2—C2 | 78.6 (4) |
N2—C2—C2i | 113.2 (2) | O1i—N2—C2 | 165.4 (3) |
C3—C2—C2i | 115.7 (5) | N1i—N2—O2 | 27.2 (4) |
C1—C2—C2i | 2.8 (3) | O1i—N2—O2 | 88.7 (2) |
C6i—C3—C5i | 122 (5) | N1i—N2—C1i | 65.2 (4) |
C6i—C3—C4 | 122 (5) | O1i—N2—C1i | 178.7 (4) |
C5i—C3—C4 | 0.9 (9) | C2—N2—C1i | 13.4 (2) |
C6i—C3—C2 | 5 (4) | O2—N2—C1i | 92.5 (2) |
C5i—C3—C2 | 118.3 (7) | N2i—O1—N1 | 22.3 (2) |
C6i—C3—C1i | 14 (5) | N2i—O1—O2i | 57.4 (2) |
C5i—C3—C1i | 108.6 (7) | N1—O1—O2i | 35.04 (13) |
C4—C3—C1i | 109.3 (7) | O2i—O2—N1i | 126.4 (2) |
C2—C3—C1i | 9.7 (3) | O2i—O2—N2 | 141.01 (11) |
C5i—C4—C3 | 8 (7) | N1i—O2—N2 | 14.6 (2) |
C5i—C4—C4i | 119 (7) | O2i—O2—N1 | 31.86 (12) |
C3—C4—C4i | 125.3 (5) | N1i—O2—N1 | 94.5 (3) |
C5i—C4—C5 | 114 (8) | O2i—O2—O1i | 174.85 (10) |
C4i—C4—C5 | 5.0 (8) | N1i—O2—O1i | 48.5 (2) |
C5i—C4—C6i | 6 (8) | N2—O2—O1i | 33.87 (12) |
C3—C4—C6i | 7.4 (5) | N1—O2—O1i | 143.0 (2) |
C4i—C4—C6i | 117.9 (5) | Cl5i—Cl4—C4 | 70 (4) |
C5—C4—C6i | 113.0 (11) | Cl5i—Cl4—C5i | 66 (4) |
C5i—C4—Cl5i | 117 (7) | C4—Cl4—C5i | 3.9 (6) |
C3—C4—Cl5i | 110.9 (7) | Cl4i—Cl5—C4i | 103 (4) |
C4i—C4—Cl5i | 123.8 (4) | Cl4i—Cl5—C5 | 107 (4) |
C5—C4—Cl5i | 128.8 (10) | C4i—Cl5—C5 | 4.3 (6) |
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1/2, −y+3/2, −z; (iii) x−1/2, −y+3/2, z−1/2; (iv) x+1/2, −y+3/2, z+1/2; (v) −x+3/2, −y+3/2, −z+1. |
(Art) 5,6-dichlorobenzfurazan-1-oxide
top
Crystal data top
C6H2Cl2N2O2 | F(000) = 408 |
Mr = 205.00 | Dx = 1.816 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.554 (2) Å | Cell parameters from 24 reflections |
b = 8.926 (2) Å | θ = 14–23° |
c = 7.310 (6) Å | µ = 0.82 mm−1 |
β = 96.10 (4)° | T = 297 K |
V = 749.6 (7) Å3 | Sword-shaped, yellow |
Z = 4 | 0.50 × 0.28 × 0.12 mm |
Data collection top
CAD-4 diffractometer | 780 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.024 |
Graphite monochromator | θmax = 28°, θmin = 2.9° |
ω–2θ scans | h = −15→15 |
Absorption correction: psi scan North, A. C. T., Phillips, D. C., and Mathews, F. S. (1968).
Acta Cryst., A24, 351-359. | k = 0→11 |
Tmin = 0.74, Tmax = 0.90 | l = −9→9 |
1811 measured reflections | 3 standard reflections every 50 min |
908 independent reflections | intensity decay: <1% |
Refinement top
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)] = 0.035 | Idealized positions |
wR(F2) = 0.085 | Calculated w = 1/[σ2(Fo2) + (0.032P)2 + 0.15P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = −0.02 |
908 reflections | Δρmax = 0.37 e Å−3 |
110 parameters | Δρmin = −0.21 e Å−3 |
33 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.055 (4) |
Crystal data top
C6H2Cl2N2O2 | V = 749.6 (7) Å3 |
Mr = 205.00 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 11.554 (2) Å | µ = 0.82 mm−1 |
b = 8.926 (2) Å | T = 297 K |
c = 7.310 (6) Å | 0.50 × 0.28 × 0.12 mm |
β = 96.10 (4)° | |
Data collection top
CAD-4 diffractometer | 780 reflections with I > 2σ(I) |
Absorption correction: psi scan North, A. C. T., Phillips, D. C., and Mathews, F. S. (1968).
Acta Cryst., A24, 351-359. | Rint = 0.024 |
Tmin = 0.74, Tmax = 0.90 | 3 standard reflections every 50 min |
1811 measured reflections | intensity decay: <1% |
908 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.035 | 33 restraints |
wR(F2) = 0.085 | Idealized positions |
S = 1.09 | Δρmax = 0.37 e Å−3 |
908 reflections | Δρmin = −0.21 e Å−3 |
110 parameters | |
Special details top
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 on F2 for ALL reflections except for 0 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.5406 (9) | 0.2445 (6) | 0.2823 (19) | 0.0389 (15) | 0.50 |
C2 | 0.4286 (8) | 0.2512 (7) | 0.190 (2) | 0.0390 (15) | 0.50 |
C3 | 0.3802 (8) | 0.3949 (15) | 0.1544 (13) | 0.0435 (13) | 0.50 |
H3 | 0.3048 | 0.4040 | 0.0953 | 0.052* | 0.50 |
C4 | 0.4448 (11) | 0.5200 (15) | 0.2085 (18) | 0.0387 (11) | 0.50 |
C5 | 0.5629 (10) | 0.5011 (14) | 0.3005 (17) | 0.0387 (10) | 0.50 |
C6 | 0.6111 (8) | 0.3672 (14) | 0.3405 (13) | 0.0448 (13) | 0.50 |
H6 | 0.6849 | 0.3573 | 0.4023 | 0.054* | 0.50 |
N1 | 0.5697 (3) | 0.1013 (4) | 0.3083 (7) | 0.0524 (8) | 0.50 |
N2 | 0.3867 (3) | 0.1148 (5) | 0.1545 (7) | 0.0549 (9) | 0.50 |
O1 | 0.6548 (3) | 0.0319 (3) | 0.3815 (5) | 0.0712 (9) | 0.50 |
O2 | 0.4717 (2) | 0.0169 (3) | 0.2254 (6) | 0.0625 (8) | 0.50 |
Cl4 | 0.3818 (6) | 0.6920 (7) | 0.1609 (10) | 0.0538 (7) | 0.50 |
Cl5 | 0.6336 (6) | 0.6686 (7) | 0.3534 (10) | 0.0504 (6) | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.031 (5) | 0.0399 (14) | 0.044 (4) | −0.0013 (13) | −0.005 (3) | −0.0023 (14) |
C2 | 0.027 (4) | 0.0428 (14) | 0.045 (4) | −0.0008 (13) | −0.006 (3) | −0.002 (2) |
C3 | 0.042 (2) | 0.036 (4) | 0.0517 (14) | 0.007 (2) | −0.0003 (13) | −0.002 (2) |
C4 | 0.040 (2) | 0.034 (3) | 0.042 (2) | −0.005 (2) | 0.0033 (13) | −0.006 (2) |
C5 | 0.037 (2) | 0.035 (3) | 0.043 (2) | −0.005 (2) | 0.0007 (14) | −0.005 (2) |
C6 | 0.043 (2) | 0.038 (4) | 0.0520 (14) | 0.008 (2) | −0.0012 (13) | −0.001 (2) |
N1 | 0.037 (2) | 0.0449 (15) | 0.072 (2) | −0.0025 (13) | −0.009 (2) | −0.0039 (14) |
N2 | 0.040 (2) | 0.047 (2) | 0.075 (2) | −0.0023 (13) | −0.009 (2) | −0.0072 (14) |
O1 | 0.0551 (15) | 0.048 (2) | 0.104 (2) | 0.0106 (14) | −0.0219 (15) | 0.005 (2) |
O2 | 0.045 (2) | 0.0419 (13) | 0.098 (3) | −0.0051 (10) | −0.007 (2) | −0.0051 (15) |
Cl4 | 0.0523 (15) | 0.042 (2) | 0.0659 (11) | 0.0031 (8) | −0.0011 (9) | 0.0020 (9) |
Cl5 | 0.0487 (14) | 0.037 (2) | 0.0644 (11) | −0.0061 (9) | 0.0003 (10) | −0.0051 (9) |
Geometric parameters (Å, º) top
C1—C2 | 1.397 (6) | N1—O1 | 1.235 (5) |
C2—C3 | 1.412 (10) | N1—O2 | 1.439 (4) |
C3—C4 | 1.378 (14) | N2—O2 | 1.374 (4) |
C4—C5 | 1.465 (5) | C4—Cl4 | 1.719 (14) |
C1—C6 | 1.404 (10) | C5—C6 | 1.337 (13) |
C1—N1 | 1.330 (8) | C5—Cl5 | 1.728 (13) |
C2—N2 | 1.326 (8) | | |
| | | |
C1···C2i | 0.396 (14) | C6···C3i | 0.27 (2) |
C1···C1i | 1.01 (2) | C6···C2i | 1.145 (12) |
C1···N2i | 1.475 (9) | C6···C4i | 1.53 (2) |
C1···C3i | 1.662 (11) | N1···N2i | 0.559 (4) |
C1···N1i | 1.875 (8) | N1···O2i | 0.912 (4) |
C2···C1i | 0.396 (14) | N1···C2i | 1.338 (7) |
C2···C6i | 1.145 (12) | N1···N1i | 1.740 (8) |
C2···N1i | 1.338 (7) | N1···C1i | 1.875 (8) |
C2···C2i | 1.786 (14) | N2···N1i | 0.559 (4) |
C3···C6i | 0.27 (2) | N2···O1i | 0.905 (5) |
C3···C5i | 1.18 (2) | N2···C1i | 1.475 (10) |
C3···C1i | 1.662 (11) | O1···N2i | 0.905 (5) |
C4···C5i | 0.20 (2) | O1···O2i | 1.588 (4) |
C4···C4i | 1.35 (2) | O2···O2i | 0.712 (5) |
C4···C6i | 1.53 (2) | O2···N1i | 0.912 (4) |
C4···Cl5i | 1.64 (2) | O2···O1i | 1.588 (4) |
C5···C4i | 0.20 (2) | Cl4···Cl5i | 0.287 (8) |
C5···C3i | 1.18 (2) | Cl4···C5i | 1.83 (2) |
C5···C5i | 1.56 (2) | Cl5···Cl4i | 0.287 (8) |
C5···Cl4i | 1.83 (2) | Cl5···C4i | 1.64 (2) |
| | | |
N1—C1—C2 | 108.5 (5) | C6i—C4—Cl5i | 116.5 (8) |
N1—C1—C6 | 125.3 (9) | C5i—C4—Cl4 | 122 (8) |
C2—C1—C6 | 126.2 (9) | C4i—C4—Cl4 | 116.7 (4) |
N2—C2—C1 | 110.8 (5) | C6i—C4—Cl4 | 126.0 (8) |
N2—C2—C3 | 132.1 (8) | Cl5i—C4—Cl4 | 9.4 (3) |
C1—C2—C3 | 117.1 (8) | C4i—C5—C3i | 172 (8) |
C4—C3—C2 | 119.5 (10) | C4i—C5—C6 | 173 (8) |
C3—C4—C5 | 119.2 (15) | C3i—C5—C6 | 9.9 (7) |
C3—C4—Cl4 | 117.4 (9) | C4i—C5—C4 | 52 (7) |
C5—C4—Cl4 | 123.4 (11) | C3i—C5—C4 | 133.2 (16) |
C6—C5—C4 | 123.3 (14) | C4i—C5—C5i | 59 (8) |
C6—C5—Cl5 | 123.2 (8) | C3i—C5—C5i | 126.6 (7) |
C4—C5—Cl5 | 113.4 (12) | C6—C5—C5i | 116.7 (6) |
C5—C6—C1 | 114.6 (10) | C4—C5—C5i | 6.7 (10) |
O1—N1—C1 | 136.1 (5) | C4i—C5—Cl5 | 62 (8) |
O1—N1—O2 | 118.3 (3) | C3i—C5—Cl5 | 113.3 (9) |
C1—N1—O2 | 105.6 (4) | C5i—C5—Cl5 | 120.1 (4) |
C2—N2—O2 | 106.3 (4) | C4i—C5—Cl4i | 53 (8) |
N2—O2—N1 | 108.9 (3) | C3i—C5—Cl4i | 122.0 (9) |
C2i—C1—C1i | 171 (3) | C6—C5—Cl4i | 131.8 (9) |
C2i—C1—N1 | 82.7 (19) | C4—C5—Cl4i | 104.8 (11) |
C1i—C1—N1 | 106.0 (4) | C5i—C5—Cl4i | 111.4 (4) |
C2i—C1—C2 | 169 (2) | Cl5—C5—Cl4i | 8.6 (3) |
C1i—C1—C2 | 2.7 (8) | C3i—C6—C2i | 177 (5) |
C2i—C1—C6 | 42.6 (16) | C3i—C6—C5 | 49 (5) |
C1i—C1—C6 | 128.7 (6) | C2i—C6—C5 | 128.1 (11) |
C2i—C1—N2i | 60.5 (18) | C3i—C6—C1 | 164 (6) |
C1i—C1—N2i | 128.2 (3) | C2i—C6—C1 | 13.5 (7) |
N1—C1—N2i | 22.2 (2) | C3i—C6—C4i | 50 (5) |
C2—C1—N2i | 130.7 (5) | C2i—C6—C4i | 127.5 (10) |
C6—C1—N2i | 103.0 (8) | C5—C6—C4i | 0.9 (11) |
C2i—C1—C3i | 45.3 (15) | C1—C6—C4i | 114.0 (9) |
C1i—C1—C3i | 126.1 (6) | N2i—N1—O2i | 136.7 (9) |
N1—C1—C3i | 127.9 (8) | N2i—N1—O1 | 42.5 (7) |
C2—C1—C3i | 123.7 (9) | O2i—N1—O1 | 94.2 (4) |
C6—C1—C3i | 2.6 (10) | N2i—N1—C1 | 93.6 (9) |
N2i—C1—C3i | 105.6 (7) | O2i—N1—C1 | 129.7 (5) |
C2i—C1—N1i | 146 (2) | N2i—N1—C2i | 76.6 (7) |
C1i—C1—N1i | 43.0 (3) | O2i—N1—C2i | 146.7 (5) |
N1—C1—N1i | 63.1 (3) | O1—N1—C2i | 119.1 (5) |
C2—C1—N1i | 45.4 (3) | C1—N1—C2i | 17.0 (6) |
C6—C1—N1i | 171.7 (8) | N2i—N1—O2 | 160.8 (9) |
N2i—C1—N1i | 85.3 (3) | O2i—N1—O2 | 24.1 (2) |
C3i—C1—N1i | 169.1 (7) | C2i—N1—O2 | 122.6 (5) |
C1i—C2—C6i | 124 (2) | N2i—N1—N1i | 167.6 (7) |
C1i—C2—N2 | 104.5 (17) | O2i—N1—N1i | 55.7 (3) |
C6i—C2—N2 | 131.6 (8) | O1—N1—N1i | 149.9 (2) |
C1i—C2—N1i | 80.3 (16) | C1—N1—N1i | 74.0 (4) |
C6i—C2—N1i | 155.8 (9) | C2i—N1—N1i | 91.0 (3) |
N2—C2—N1i | 24.2 (2) | O2—N1—N1i | 31.6 (2) |
C1i—C2—C1 | 7 (2) | N2i—N1—C1i | 124.6 (8) |
C6i—C2—C1 | 117.6 (10) | O2i—N1—C1i | 98.7 (4) |
N1i—C2—C1 | 86.5 (5) | O1—N1—C1i | 167.1 (4) |
C1i—C2—C3 | 123 (2) | C1—N1—C1i | 31.0 (6) |
C6i—C2—C3 | 0.6 (10) | C2i—N1—C1i | 48.0 (3) |
N1i—C2—C3 | 156.3 (8) | O2—N1—C1i | 74.6 (4) |
C1i—C2—C2i | 9.0 (18) | N1i—N1—C1i | 43.0 (3) |
C6i—C2—C2i | 115.2 (7) | N1i—N2—O1i | 112.8 (9) |
N2—C2—C2i | 113.2 (3) | N1i—N2—C2 | 79.2 (7) |
N1i—C2—C2i | 89.0 (3) | O1i—N2—C2 | 168.0 (5) |
C1—C2—C2i | 2.5 (5) | N1i—N2—O2 | 27.1 (6) |
C3—C2—C2i | 114.7 (6) | O1i—N2—O2 | 85.7 (4) |
C6i—C3—C5i | 121 (5) | N1i—N2—C1i | 64.1 (8) |
C6i—C3—C4 | 122 (5) | O1i—N2—C1i | 176.9 (5) |
C5i—C3—C4 | 1.1 (12) | C2—N2—C1i | 15.0 (4) |
C6i—C3—C2 | 3 (4) | O2—N2—C1i | 91.2 (4) |
C5i—C3—C2 | 118.7 (9) | N2i—O1—N1 | 24.7 (3) |
C6i—C3—C1i | 14 (5) | N2i—O1—O2i | 59.6 (3) |
C5i—C3—C1i | 107.3 (9) | N1—O1—O2i | 35.0 (2) |
C4—C3—C1i | 108.0 (9) | O2i—O2—N1i | 124.3 (3) |
C2—C3—C1i | 11.5 (6) | O2i—O2—N2 | 140.5 (2) |
C5i—C4—C4i | 121 (8) | N1i—O2—N2 | 16.2 (3) |
C5i—C4—C3 | 7 (7) | O2i—O2—N1 | 31.6 (2) |
C4i—C4—C3 | 125.8 (7) | N1i—O2—N1 | 92.7 (4) |
C5i—C4—C5 | 115 (8) | O2i—O2—O1i | 175.1 (2) |
C4i—C4—C5 | 6.7 (10) | N1i—O2—O1i | 50.9 (3) |
C5i—C4—C6i | 6 (7) | N2—O2—O1i | 34.7 (2) |
C4i—C4—C6i | 117.3 (6) | N1—O2—O1i | 143.6 (3) |
C3—C4—C6i | 8.5 (6) | Cl5i—Cl4—C4 | 70 (3) |
C5—C4—C6i | 110.7 (14) | Cl5i—Cl4—C5i | 65 (3) |
C5i—C4—Cl5i | 112 (8) | C4—Cl4—C5i | 5.3 (6) |
C4i—C4—Cl5i | 126.1 (4) | Cl4i—Cl5—C4i | 101 (3) |
C3—C4—Cl5i | 108.0 (8) | Cl4i—Cl5—C5 | 107 (3) |
C5—C4—Cl5i | 132.8 (12) | C4i—Cl5—C5 | 6.1 (7) |
Symmetry code: (i) −x+1, y, −z+1/2. |
(Blt) 5,6-dichlorobenzfurazan-1-oxide
top
Crystal data top
C6H2Cl2N2O2 | F(000) = 408 |
Mr = 205.00 | Dx = 1.840 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3250 reflections |
a = 7.0679 (6) Å | θ = 2–25° |
b = 11.7502 (9) Å | µ = 0.83 mm−1 |
c = 9.0114 (7) Å | T = 173 K |
β = 98.563 (1)° | Prism, yellow |
V = 740.05 (10) Å3 | 0.5 × 0.35 × 0.3 mm |
Z = 4 | |
Data collection top
SMART diffractometer | 1305 independent reflections |
Radiation source: fine-focus sealed tube | 1145 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
ω scans | θmax = 25.0°, θmin = 2.9° |
Absorption correction: SADABS (sheldrick,1996) ? | h = −8→8 |
Tmin = 0.63, Tmax = 0.81 | k = −11→13 |
3699 measured reflections | l = −10→10 |
Refinement top
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | Idealized positions |
S = 1.04 | Calculated w = 1/[σ2(Fo2) + (0.065P)2 + 0.91P] where P = (Fo2 + 2Fc2)/3 |
1305 reflections | (Δ/σ)max = 0.03 |
218 parameters | Δρmax = 0.47 e Å−3 |
113 restraints | Δρmin = −0.50 e Å−3 |
Crystal data top
C6H2Cl2N2O2 | V = 740.05 (10) Å3 |
Mr = 205.00 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.0679 (6) Å | µ = 0.83 mm−1 |
b = 11.7502 (9) Å | T = 173 K |
c = 9.0114 (7) Å | 0.5 × 0.35 × 0.3 mm |
β = 98.563 (1)° | |
Data collection top
SMART diffractometer | 1305 independent reflections |
Absorption correction: SADABS (sheldrick,1996) ? | 1145 reflections with I > 2σ(I) |
Tmin = 0.63, Tmax = 0.81 | Rint = 0.016 |
3699 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.038 | 113 restraints |
wR(F2) = 0.110 | Idealized positions |
S = 1.04 | Δρmax = 0.47 e Å−3 |
1305 reflections | Δρmin = −0.50 e Å−3 |
218 parameters | |
Special details top
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 on F2 for ALL reflections except for 0 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.1896 (3) | 0.4137 (4) | −0.2518 (6) | 0.0242 (12) | 0.622 (4) |
C2 | 0.0951 (3) | 0.3091 (3) | −0.2555 (6) | 0.0250 (11) | 0.622 (4) |
C3 | 0.0561 (5) | 0.2584 (5) | −0.1212 (7) | 0.0273 (10) | 0.622 (4) |
H3 | −0.0080 | 0.1873 | −0.1213 | 0.033* | 0.62 |
C4 | 0.1142 (6) | 0.3157 (6) | 0.0075 (7) | 0.0242 (8) | 0.622 (4) |
C5 | 0.2121 (6) | 0.4240 (6) | 0.0108 (7) | 0.0211 (8) | 0.622 (4) |
C6 | 0.2510 (5) | 0.4745 (5) | −0.1173 (7) | 0.0243 (10) | 0.622 (4) |
H6 | 0.3150 | 0.5456 | −0.1165 | 0.029* | 0.62 |
N1 | 0.2067 (4) | 0.4407 (4) | −0.3937 (6) | 0.0343 (11) | 0.622 (4) |
N2 | 0.0517 (4) | 0.2686 (4) | −0.3948 (6) | 0.0363 (11) | 0.622 (4) |
O1 | 0.2753 (4) | 0.5204 (3) | −0.4562 (4) | 0.0460 (10) | 0.622 (4) |
O2 | 0.1195 (3) | 0.3488 (3) | −0.4852 (4) | 0.0401 (10) | 0.622 (4) |
Cl4 | 0.0718 (7) | 0.2592 (5) | 0.1750 (5) | 0.0368 (7) | 0.622 (4) |
Cl5 | 0.2816 (7) | 0.4910 (5) | 0.1826 (4) | 0.0241 (5) | 0.622 (4) |
C21 | 0.1242 (4) | 0.3440 (5) | −0.2617 (7) | 0.0247 (13) | 0.378 (4) |
C22 | 0.2116 (4) | 0.4509 (4) | −0.2462 (7) | 0.0237 (14) | 0.378 (4) |
C23 | 0.2549 (7) | 0.5019 (6) | −0.1032 (9) | 0.0233 (12) | 0.378 (4) |
H23 | 0.3144 | 0.5744 | −0.0904 | 0.028* | 0.38 |
C24 | 0.2079 (9) | 0.4425 (8) | 0.0144 (8) | 0.0206 (9) | 0.378 (4) |
C25 | 0.1173 (9) | 0.3319 (8) | −0.0021 (8) | 0.0240 (9) | 0.378 (4) |
C26 | 0.0744 (7) | 0.2812 (6) | −0.1388 (8) | 0.0274 (12) | 0.378 (4) |
H26 | 0.0150 | 0.2086 | −0.1511 | 0.033* | 0.38 |
N21 | 0.1008 (5) | 0.3173 (4) | −0.4078 (6) | 0.0338 (14) | 0.378 (4) |
N22 | 0.2445 (6) | 0.4931 (4) | −0.3775 (7) | 0.0340 (14) | 0.378 (4) |
O21 | 0.0338 (6) | 0.2363 (4) | −0.4847 (5) | 0.0381 (15) | 0.378 (4) |
O22 | 0.1769 (5) | 0.4117 (4) | −0.4822 (5) | 0.036 (2) | 0.378 (4) |
Cl24 | 0.2563 (12) | 0.4991 (10) | 0.1915 (7) | 0.039 (2) | 0.378 (4) |
Cl25 | 0.0625 (13) | 0.2623 (9) | 0.1566 (6) | 0.0410 (14) | 0.378 (4) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.026 (2) | 0.021 (4) | 0.026 (2) | 0.004 (2) | 0.0047 (13) | 0.000 (2) |
C2 | 0.023 (2) | 0.022 (3) | 0.029 (2) | 0.002 (2) | 0.0009 (14) | −0.004 (2) |
C3 | 0.025 (2) | 0.017 (2) | 0.038 (2) | −0.0017 (15) | −0.0023 (14) | 0.001 (2) |
C4 | 0.0236 (13) | 0.019 (2) | 0.029 (2) | 0.0025 (12) | 0.0003 (11) | 0.0056 (13) |
C5 | 0.0213 (13) | 0.015 (2) | 0.0262 (14) | 0.0065 (12) | 0.0021 (11) | −0.0033 (13) |
C6 | 0.0264 (14) | 0.010 (3) | 0.038 (2) | 0.0042 (14) | 0.0080 (13) | −0.001 (2) |
N1 | 0.033 (2) | 0.039 (3) | 0.030 (2) | −0.003 (2) | 0.002 (2) | −0.002 (3) |
N2 | 0.030 (2) | 0.046 (3) | 0.033 (2) | −0.001 (2) | 0.000 (2) | −0.008 (3) |
O1 | 0.060 (2) | 0.049 (2) | 0.032 (2) | −0.013 (2) | 0.016 (2) | 0.009 (2) |
O2 | 0.039 (2) | 0.052 (3) | 0.028 (2) | −0.007 (2) | 0.003 (2) | −0.010 (2) |
Cl4 | 0.0363 (13) | 0.0388 (12) | 0.0335 (10) | −0.0063 (10) | −0.0012 (9) | 0.0149 (9) |
Cl5 | 0.0185 (9) | 0.0266 (10) | 0.0271 (8) | 0.0043 (7) | 0.0034 (6) | −0.0104 (6) |
C21 | 0.023 (2) | 0.022 (3) | 0.028 (2) | 0.002 (2) | 0.001 (2) | −0.003 (2) |
C22 | 0.026 (2) | 0.019 (4) | 0.026 (2) | 0.004 (2) | 0.0050 (15) | 0.001 (2) |
C23 | 0.026 (2) | 0.008 (3) | 0.037 (2) | 0.006 (2) | 0.0087 (14) | −0.002 (2) |
C24 | 0.0207 (14) | 0.014 (2) | 0.0262 (15) | 0.0070 (13) | 0.0024 (12) | −0.0034 (14) |
C25 | 0.0237 (14) | 0.019 (2) | 0.028 (2) | 0.0033 (14) | 0.0003 (13) | 0.0059 (15) |
C26 | 0.025 (2) | 0.016 (3) | 0.038 (2) | −0.002 (2) | −0.002 (2) | 0.001 (2) |
N21 | 0.024 (3) | 0.044 (4) | 0.031 (2) | −0.002 (2) | 0.000 (2) | −0.006 (3) |
N22 | 0.033 (2) | 0.039 (4) | 0.030 (2) | −0.003 (2) | 0.004 (2) | −0.002 (4) |
O21 | 0.048 (3) | 0.035 (3) | 0.031 (3) | −0.009 (2) | 0.004 (3) | −0.012 (2) |
O22 | 0.029 (3) | 0.054 (4) | 0.025 (3) | −0.011 (3) | 0.000 (2) | 0.000 (3) |
Cl24 | 0.033 (3) | 0.043 (2) | 0.041 (2) | 0.006 (2) | 0.0042 (15) | −0.0134 (14) |
Cl25 | 0.037 (2) | 0.045 (2) | 0.039 (2) | −0.006 (2) | −0.002 (2) | 0.019 (2) |
Geometric parameters (Å, º) top
C1—C2 | 1.397 (5) | C21—N21 | 1.340 (7) |
C2—C3 | 1.413 (7) | C21—C22 | 1.397 (5) |
C3—C4 | 1.351 (8) | C21—C26 | 1.418 (7) |
C4—C5 | 1.447 (4) | C22—N22 | 1.335 (7) |
C5—C6 | 1.361 (8) | C22—C23 | 1.413 (7) |
C1—C6 | 1.418 (7) | C23—C24 | 1.351 (8) |
C1—N1 | 1.340 (7) | C24—C25 | 1.447 (4) |
C2—N2 | 1.335 (7) | C24—Cl24 | 1.716 (7) |
N1—O1 | 1.230 (5) | C25—C26 | 1.361 (8) |
N1—O2 | 1.440 (5) | C25—Cl25 | 1.740 (6) |
N2—O2 | 1.377 (5) | N21—O21 | 1.230 (5) |
C4—Cl4 | 1.716 (7) | N21—O22 | 1.440 (5) |
C5—Cl5 | 1.740 (6) | N22—O22 | 1.377 (5) |
| | | |
C2—C1—C6 | 123.2 (6) | N21—C21—C22 | 107.2 (5) |
C1—C2—C3 | 120.3 (6) | N21—C21—C26 | 129.6 (5) |
C4—C3—C2 | 116.9 (5) | C22—C21—C26 | 123.2 (6) |
C3—C4—C5 | 122.7 (7) | N22—C22—C21 | 112.2 (6) |
C6—C5—C4 | 121.4 (6) | N22—C22—C23 | 127.5 (4) |
C5—C6—C1 | 115.5 (5) | C21—C22—C23 | 120.3 (6) |
N1—C1—C2 | 107.2 (5) | C24—C23—C22 | 116.9 (5) |
N2—C2—C1 | 112.2 (6) | C23—C24—C25 | 122.7 (7) |
C1—N1—O2 | 106.1 (4) | C23—C24—Cl24 | 119.5 (5) |
C2—N2—O2 | 105.1 (4) | C25—C24—Cl24 | 117.9 (6) |
N2—O2—N1 | 109.3 (3) | C26—C25—C24 | 121.4 (7) |
O1—N1—O2 | 118.2 (4) | C26—C25—Cl25 | 119.4 (5) |
C5—C4—Cl4 | 117.9 (6) | C24—C25—Cl25 | 119.1 (6) |
C4—C5—Cl5 | 119.1 (6) | C25—C26—C21 | 115.5 (5) |
N1—C1—C6 | 129.6 (5) | O21—N21—C21 | 135.7 (5) |
N2—C2—C3 | 127.5 (4) | O21—N21—O22 | 118.2 (4) |
C3—C4—Cl4 | 119.5 (5) | C21—N21—O22 | 106.1 (4) |
C6—C5—Cl5 | 119.4 (5) | C22—N22—O22 | 105.1 (4) |
O1—N1—C1 | 135.7 (5) | N22—O22—N21 | 109.4 (3) |
(Brt) 5,6-dichlorobenzfurazan-1.oxide
top
Crystal data top
C6H2Cl2N2O2 | F(000) = 408 |
Mr = 205.00 | Dx = 1.788 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2148 reflections |
a = 7.1739 (2) Å | θ = 2–25° |
b = 11.8351 (2) Å | µ = 0.80 mm−1 |
c = 9.0639 (1) Å | T = 297 K |
β = 98.350 (1)° | Prism, yellow |
V = 761.40 (3) Å3 | 0.50 × 0.35 × 0.30 mm |
Z = 4 | |
Data collection top
SMART diffractometer | 1330 independent reflections |
Radiation source: fine-focus sealed tube | 1158 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
ω scans | θmax = 25°, θmin = 2.9° |
Absorption correction: SADABS (sheldrick,1996) ? | h = −8→8 |
Tmin = 0.47, Tmax = 0.82 | k = −13→14 |
3751 measured reflections | l = −9→10 |
Refinement top
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | Idealized positions |
S = 1.73 | Calculated w = 1/[σ2(Fo2) + (0.045P)2 + 0.027P] where P = (Fo2 + 2Fc2)/3 |
1330 reflections | (Δ/σ)max = 0.04 |
218 parameters | Δρmax = 0.37 e Å−3 |
113 restraints | Δρmin = −0.31 e Å−3 |
Crystal data top
C6H2Cl2N2O2 | V = 761.40 (3) Å3 |
Mr = 205.00 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.1739 (2) Å | µ = 0.80 mm−1 |
b = 11.8351 (2) Å | T = 297 K |
c = 9.0639 (1) Å | 0.50 × 0.35 × 0.30 mm |
β = 98.350 (1)° | |
Data collection top
SMART diffractometer | 1330 independent reflections |
Absorption correction: SADABS (sheldrick,1996) ? | 1158 reflections with I > 2σ(I) |
Tmin = 0.47, Tmax = 0.82 | Rint = 0.015 |
3751 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.036 | 113 restraints |
wR(F2) = 0.107 | Idealized positions |
S = 1.73 | Δρmax = 0.37 e Å−3 |
1330 reflections | Δρmin = −0.31 e Å−3 |
218 parameters | |
Special details top
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 on F2 for ALL reflections except for 0 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.1864 (3) | 0.4117 (3) | −0.2501 (6) | 0.0389 (12) | 0.610 (3) |
C2 | 0.0931 (3) | 0.3082 (3) | −0.2526 (6) | 0.0400 (11) | 0.610 (3) |
C3 | 0.0541 (5) | 0.2603 (5) | −0.1160 (7) | 0.0430 (11) | 0.610 (3) |
H3 | −0.0078 | 0.1914 | −0.1142 | 0.052* | 0.61 |
C4 | 0.1102 (6) | 0.3185 (6) | 0.0102 (7) | 0.0397 (8) | 0.610 (3) |
C5 | 0.2069 (6) | 0.4259 (6) | 0.0090 (7) | 0.0384 (8) | 0.610 (3) |
C6 | 0.2460 (5) | 0.4737 (5) | −0.1197 (7) | 0.0417 (11) | 0.610 (3) |
H6 | 0.3079 | 0.5426 | −0.1211 | 0.050* | 0.61 |
N1 | 0.2059 (4) | 0.4381 (4) | −0.3912 (5) | 0.0571 (10) | 0.610 (3) |
N2 | 0.0528 (4) | 0.2678 (3) | −0.3902 (5) | 0.0610 (11) | 0.610 (3) |
O1 | 0.2750 (4) | 0.5169 (3) | −0.4533 (4) | 0.0796 (12) | 0.610 (3) |
O2 | 0.1206 (3) | 0.3461 (3) | −0.4803 (3) | 0.0685 (11) | 0.610 (3) |
Cl4 | 0.0686 (7) | 0.2665 (5) | 0.1790 (5) | 0.0581 (7) | 0.610 (3) |
Cl5 | 0.2762 (7) | 0.4966 (5) | 0.1768 (5) | 0.0509 (8) | 0.610 (3) |
C21 | 0.1316 (4) | 0.3435 (4) | −0.2578 (7) | 0.038 (2) | 0.390 (3) |
C22 | 0.2172 (4) | 0.4494 (4) | −0.2417 (6) | 0.0372 (15) | 0.390 (3) |
C23 | 0.2616 (6) | 0.4972 (6) | −0.0964 (8) | 0.0395 (14) | 0.390 (3) |
H23 | 0.3188 | 0.5677 | −0.0822 | 0.047* | 0.39 |
C24 | 0.2177 (8) | 0.4366 (7) | 0.0193 (8) | 0.0376 (11) | 0.390 (3) |
C25 | 0.1288 (9) | 0.3267 (8) | −0.0012 (7) | 0.0405 (11) | 0.390 (3) |
C26 | 0.0847 (7) | 0.2789 (6) | −0.1385 (7) | 0.043 (2) | 0.390 (3) |
H26 | 0.0276 | 0.2084 | −0.1523 | 0.052* | 0.39 |
N21 | 0.1049 (5) | 0.3177 (4) | −0.4037 (6) | 0.0584 (14) | 0.390 (3) |
N22 | 0.2458 (5) | 0.4920 (4) | −0.3721 (7) | 0.0578 (13) | 0.390 (3) |
O21 | 0.0374 (6) | 0.2376 (4) | −0.4799 (5) | 0.0669 (15) | 0.390 (3) |
O22 | 0.1778 (5) | 0.4126 (3) | −0.4763 (4) | 0.064 (2) | 0.390 (3) |
Cl24 | 0.2668 (11) | 0.4880 (8) | 0.1976 (6) | 0.0522 (13) | 0.390 (3) |
Cl25 | 0.0758 (12) | 0.2526 (8) | 0.1539 (6) | 0.0643 (15) | 0.390 (3) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.035 (2) | 0.039 (3) | 0.043 (2) | −0.005 (2) | 0.0068 (14) | −0.002 (2) |
C2 | 0.031 (2) | 0.042 (3) | 0.046 (2) | −0.004 (2) | 0.0028 (15) | −0.009 (2) |
C3 | 0.039 (2) | 0.037 (2) | 0.052 (2) | −0.006 (2) | 0.006 (2) | 0.000 (2) |
C4 | 0.0336 (15) | 0.041 (2) | 0.0443 (15) | 0.0015 (13) | 0.0053 (12) | 0.0045 (13) |
C5 | 0.0324 (14) | 0.041 (2) | 0.0413 (15) | 0.0035 (13) | 0.0024 (12) | −0.0050 (13) |
C6 | 0.043 (2) | 0.034 (2) | 0.048 (2) | −0.0015 (14) | 0.0060 (15) | −0.004 (2) |
N1 | 0.057 (2) | 0.071 (3) | 0.042 (2) | −0.006 (2) | 0.001 (2) | −0.004 (3) |
N2 | 0.054 (2) | 0.076 (3) | 0.050 (2) | −0.003 (2) | 0.001 (2) | −0.017 (3) |
O1 | 0.107 (3) | 0.084 (2) | 0.052 (2) | −0.023 (2) | 0.025 (2) | 0.011 (2) |
O2 | 0.072 (2) | 0.091 (3) | 0.043 (2) | −0.007 (2) | 0.008 (2) | −0.017 (2) |
Cl4 | 0.0621 (10) | 0.0630 (14) | 0.0488 (11) | −0.0081 (8) | 0.0064 (8) | 0.0113 (11) |
Cl5 | 0.0479 (10) | 0.060 (2) | 0.0450 (11) | −0.0032 (8) | 0.0059 (8) | −0.0155 (12) |
C21 | 0.028 (2) | 0.043 (4) | 0.043 (2) | −0.008 (2) | 0.005 (2) | −0.005 (2) |
C22 | 0.036 (2) | 0.032 (4) | 0.044 (2) | −0.006 (2) | 0.007 (2) | 0.001 (2) |
C23 | 0.043 (2) | 0.030 (3) | 0.046 (3) | 0.004 (2) | 0.008 (2) | −0.007 (2) |
C24 | 0.032 (2) | 0.037 (2) | 0.043 (2) | 0.003 (2) | 0.003 (2) | −0.005 (2) |
C25 | 0.035 (2) | 0.042 (2) | 0.044 (2) | 0.002 (2) | 0.005 (2) | 0.007 (2) |
C26 | 0.039 (2) | 0.037 (3) | 0.054 (3) | −0.008 (2) | 0.007 (2) | 0.001 (2) |
N21 | 0.048 (3) | 0.076 (4) | 0.050 (2) | −0.004 (2) | 0.001 (2) | −0.014 (3) |
N22 | 0.058 (3) | 0.071 (3) | 0.044 (2) | −0.005 (2) | 0.003 (2) | −0.002 (3) |
O21 | 0.075 (3) | 0.069 (3) | 0.055 (3) | −0.010 (2) | 0.003 (2) | −0.017 (2) |
O22 | 0.058 (3) | 0.089 (5) | 0.043 (3) | −0.014 (3) | 0.000 (2) | 0.004 (3) |
Cl24 | 0.060 (2) | 0.0510 (15) | 0.045 (2) | 0.0031 (14) | 0.0038 (13) | −0.0039 (13) |
Cl25 | 0.074 (2) | 0.065 (2) | 0.055 (2) | −0.0114 (15) | 0.0108 (15) | 0.016 (2) |
Geometric parameters (Å, º) top
C1—N1 | 1.343 (7) | C21—N21 | 1.343 (7) |
C1—C2 | 1.395 (5) | C21—C22 | 1.395 (5) |
C1—C6 | 1.404 (7) | C21—C26 | 1.404 (7) |
C2—N2 | 1.328 (7) | C22—N22 | 1.328 (7) |
C2—C3 | 1.426 (7) | C22—C23 | 1.426 (7) |
C3—C4 | 1.345 (8) | C23—C24 | 1.346 (8) |
C4—C5 | 1.449 (4) | C24—C25 | 1.449 (4) |
C4—Cl4 | 1.715 (6) | C24—Cl24 | 1.715 (6) |
C5—C6 | 1.362 (8) | C25—C26 | 1.362 (8) |
C5—Cl5 | 1.744 (6) | C25—Cl25 | 1.744 (6) |
N1—O1 | 1.231 (5) | N21—O21 | 1.231 (5) |
N1—O2 | 1.438 (4) | N21—O22 | 1.438 (5) |
N2—O2 | 1.371 (5) | N22—O22 | 1.371 (5) |
| | | |
N1—C1—C2 | 107.7 (5) | N21—C21—C22 | 107.8 (5) |
N1—C1—C6 | 128.3 (4) | N21—C21—C26 | 128.2 (4) |
C2—C1—C6 | 124.0 (6) | C22—C21—C26 | 124.0 (6) |
N2—C2—C1 | 111.7 (5) | N22—C22—C21 | 111.7 (5) |
N2—C2—C3 | 129.0 (4) | N22—C22—C23 | 129.0 (4) |
C1—C2—C3 | 119.3 (5) | C21—C22—C23 | 119.3 (5) |
C4—C3—C2 | 117.6 (5) | C24—C23—C22 | 117.5 (5) |
C3—C4—C5 | 121.8 (7) | C23—C24—C25 | 121.8 (7) |
C3—C4—Cl4 | 120.4 (5) | C23—C24—Cl24 | 120.4 (5) |
C5—C4—Cl4 | 117.8 (6) | C25—C24—Cl24 | 117.8 (6) |
C6—C5—C4 | 121.9 (6) | C26—C25—C24 | 121.9 (7) |
C6—C5—Cl5 | 118.6 (5) | C26—C25—Cl25 | 118.6 (5) |
C4—C5—Cl5 | 119.4 (6) | C24—C25—Cl25 | 119.4 (6) |
C5—C6—C1 | 115.4 (5) | C25—C26—C21 | 115.4 (5) |
O1—N1—C1 | 135.7 (4) | O21—N21—C21 | 135.7 (5) |
O1—N1—O2 | 118.9 (3) | O21—N21—O22 | 118.9 (3) |
C1—N1—O2 | 105.3 (4) | C21—N21—O22 | 105.3 (4) |
C2—N2—O2 | 105.6 (4) | C22—N22—O22 | 105.6 (4) |
N2—O2—N1 | 109.6 (3) | N22—O22—N21 | 109.7 (3) |
(Clt) 5,6-dichlorobenzfurazan-1-oxide
top
Crystal data top
C6H2Cl2N2O2 | F(000) = 408 |
Mr = 205.00 | Dx = 1.807 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.2233 (1) Å | Cell parameters from 1656 reflections |
b = 9.0549 (3) Å | θ = 2–25° |
c = 11.5700 (4) Å | µ = 0.81 mm−1 |
β = 95.315 (2)° | T = 173 K |
V = 753.50 (4) Å3 | Thick plate, yellow |
Z = 4 | 0.50 × 0.45 × 0.20 mm |
Data collection top
SMART diffractometer | 659 independent reflections |
Radiation source: fine-focus sealed tube | 594 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ω scans | θmax = 25.1°, θmin = 3.5° |
Absorption correction: SADABS (sheldrick,1996) ? | h = −8→8 |
Tmin = 0.67, Tmax = 0.85 | k = −10→7 |
3292 measured reflections | l = −13→13 |
Refinement top
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)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.073 | Idealized positions |
S = 1.12 | Calculated w = 1/[σ2(Fo2) + (0.043P)2 + 0.199P] where P = (Fo2 + 2Fc2)/3 |
659 reflections | (Δ/σ)max = 0.02 |
109 parameters | Δρmax = 0.18 e Å−3 |
33 restraints | Δρmin = −0.21 e Å−3 |
Crystal data top
C6H2Cl2N2O2 | V = 753.50 (4) Å3 |
Mr = 205.00 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 7.2233 (1) Å | µ = 0.81 mm−1 |
b = 9.0549 (3) Å | T = 173 K |
c = 11.5700 (4) Å | 0.50 × 0.45 × 0.20 mm |
β = 95.315 (2)° | |
Data collection top
SMART diffractometer | 659 independent reflections |
Absorption correction: SADABS (sheldrick,1996) ? | 594 reflections with I > 2σ(I) |
Tmin = 0.67, Tmax = 0.85 | Rint = 0.024 |
3292 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.027 | 33 restraints |
wR(F2) = 0.073 | Idealized positions |
S = 1.12 | Δρmax = 0.18 e Å−3 |
659 reflections | Δρmin = −0.21 e Å−3 |
109 parameters | |
Special details top
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 on F2 for ALL reflections except for 0 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.5311 (13) | 0.2759 (6) | 0.7869 (9) | 0.028 (2) | 0.50 |
C2 | 0.4322 (14) | 0.2843 (7) | 0.6770 (7) | 0.028 (2) | 0.50 |
C3 | 0.3963 (12) | 0.4281 (16) | 0.6298 (10) | 0.0322 (14) | 0.50 |
H3 | 0.3333 | 0.4364 | 0.5550 | 0.039* | 0.50 |
C4 | 0.4539 (16) | 0.5510 (18) | 0.6922 (9) | 0.0286 (15) | 0.50 |
C5 | 0.5525 (16) | 0.5284 (18) | 0.8080 (9) | 0.0296 (15) | 0.50 |
C6 | 0.5955 (12) | 0.3957 (15) | 0.8566 (10) | 0.0328 (14) | 0.50 |
H6 | 0.6608 | 0.3872 | 0.9280 | 0.039* | 0.50 |
N1 | 0.5552 (5) | 0.1343 (5) | 0.8159 (3) | 0.0384 (8) | 0.50 |
N2 | 0.3926 (5) | 0.1483 (5) | 0.6335 (4) | 0.0410 (8) | 0.50 |
O1 | 0.6282 (4) | 0.0635 (4) | 0.8995 (3) | 0.0513 (7) | 0.50 |
O2 | 0.4665 (4) | 0.0517 (3) | 0.7181 (2) | 0.0431 (7) | 0.50 |
Cl4 | 0.4124 (10) | 0.7204 (9) | 0.6282 (6) | 0.0368 (7) | 0.50 |
Cl5 | 0.6101 (10) | 0.6932 (9) | 0.8783 (6) | 0.0372 (7) | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.027 (4) | 0.036 (2) | 0.019 (6) | −0.0027 (13) | −0.003 (4) | −0.0005 (13) |
C2 | 0.026 (4) | 0.039 (2) | 0.018 (6) | −0.0009 (15) | −0.003 (3) | −0.0028 (14) |
C3 | 0.0348 (15) | 0.032 (5) | 0.030 (2) | 0.000 (2) | 0.0054 (15) | 0.004 (2) |
C4 | 0.0293 (14) | 0.031 (4) | 0.0259 (13) | −0.004 (2) | 0.0046 (12) | −0.008 (3) |
C5 | 0.0307 (14) | 0.032 (4) | 0.0262 (13) | −0.004 (2) | 0.0033 (12) | −0.007 (3) |
C6 | 0.0344 (14) | 0.036 (5) | 0.029 (2) | 0.000 (2) | 0.0044 (14) | 0.005 (2) |
N1 | 0.037 (2) | 0.048 (2) | 0.030 (3) | −0.0035 (15) | −0.002 (2) | 0.0005 (14) |
N2 | 0.039 (2) | 0.050 (2) | 0.032 (3) | −0.0034 (14) | −0.003 (2) | −0.0006 (14) |
O1 | 0.062 (2) | 0.044 (2) | 0.045 (2) | 0.0018 (13) | −0.0112 (13) | 0.0134 (13) |
O2 | 0.046 (2) | 0.0428 (15) | 0.039 (2) | −0.0037 (13) | −0.0018 (13) | −0.0043 (12) |
Cl4 | 0.0433 (14) | 0.035 (2) | 0.0311 (8) | 0.0018 (9) | −0.0018 (8) | 0.0026 (9) |
Cl5 | 0.043 (2) | 0.038 (2) | 0.0303 (9) | −0.0053 (10) | 0.0011 (9) | −0.0036 (10) |
Geometric parameters (Å, º) top
C1—C2 | 1.403 (7) | C2—N2 | 1.350 (9) |
C2—C3 | 1.427 (10) | N1—O1 | 1.237 (5) |
C3—C4 | 1.370 (15) | N1—O2 | 1.454 (5) |
C4—C5 | 1.472 (6) | N2—O2 | 1.383 (5) |
C5—C6 | 1.350 (15) | C4—Cl4 | 1.717 (14) |
C1—C6 | 1.405 (9) | C5—Cl5 | 1.732 (14) |
C1—N1 | 1.332 (8) | | |
| | | |
C1···C2i | 0.479 (14) | C6···C3i | 0.34 (2) |
C1···C1i | 0.93 (2) | C6···C2i | 1.093 (12) |
C1···N2i | 1.546 (10) | C6···C4i | 1.54 (3) |
C1···C3i | 1.735 (10) | N1···N2i | 0.678 (4) |
C1···N1i | 1.819 (7) | N1···O2i | 0.853 (4) |
C2···C1i | 0.479 (14) | N1···C2i | 1.363 (7) |
C2···C6i | 1.093 (12) | N1···N1i | 1.654 (8) |
C2···N1i | 1.363 (7) | N1···C1i | 1.819 (7) |
C2···C2i | 1.873 (14) | N2···N1i | 0.678 (4) |
C3···C6i | 0.34 (2) | N2···O1i | 0.865 (4) |
C3···C5i | 1.20 (3) | N2···C1i | 1.546 (10) |
C3···C1i | 1.735 (10) | O1···N2i | 0.865 (4) |
C4···C5i | 0.21 (3) | O1···O2i | 1.470 (4) |
C4···C4i | 1.44 (2) | O2···O2i | 0.844 (5) |
C4···C6i | 1.54 (3) | O2···N1i | 0.853 (4) |
C4···Cl5i | 1.57 (2) | O2···O1i | 1.470 (4) |
C5···C4i | 0.21 (3) | Cl4···Cl5i | 0.300 (9) |
C5···C3i | 1.20 (3) | Cl4···C5i | 1.90 (2) |
C5···C5i | 1.48 (2) | Cl5···Cl4i | 0.300 (9) |
C5···Cl4i | 1.90 (2) | Cl5···C4i | 1.57 (2) |
| | | |
C2—C1—C6 | 126.3 (9) | C6i—C4—Cl5i | 120.6 (8) |
C1—C2—C3 | 117.1 (9) | C5i—C4—Cl4 | 147 (6) |
C4—C3—C2 | 120.3 (11) | C4i—C4—Cl4 | 116.6 (4) |
C3—C4—C5 | 117.6 (17) | C6i—C4—Cl4 | 129.1 (7) |
C6—C5—C4 | 125.2 (17) | Cl5i—C4—Cl4 | 9.2 (3) |
C5—C6—C1 | 113.4 (11) | C4i—C5—C3i | 143 (6) |
N1—C1—C2 | 108.9 (5) | C4i—C5—C6 | 156 (6) |
N2—C2—C1 | 111.2 (5) | C3i—C5—C6 | 13.5 (5) |
C1—N1—O2 | 105.2 (4) | C4i—C5—C4 | 77 (5) |
C2—N2—O2 | 105.0 (4) | C3i—C5—C4 | 138.6 (19) |
N2—O2—N1 | 109.8 (3) | C4i—C5—C5i | 84 (6) |
O1—N1—O2 | 117.8 (3) | C3i—C5—C5i | 130.6 (7) |
C5—C4—Cl4 | 124.5 (16) | C6—C5—C5i | 117.2 (6) |
C4—C5—Cl5 | 112.5 (16) | C4—C5—C5i | 8.2 (12) |
N1—C1—C6 | 124.8 (10) | C4i—C5—Cl5 | 37 (5) |
N2—C2—C3 | 131.7 (9) | C3i—C5—Cl5 | 108.9 (7) |
C3—C4—Cl4 | 117.8 (7) | C5i—C5—Cl5 | 120.5 (4) |
C6—C5—Cl5 | 122.3 (7) | C4i—C5—Cl4i | 30 (5) |
O1—N1—C1 | 137.0 (5) | C3i—C5—Cl4i | 116.0 (8) |
C2i—C1—C1i | 170 (2) | C6—C5—Cl4i | 129.5 (7) |
C2i—C1—N1 | 83.4 (16) | C4—C5—Cl4i | 105.2 (15) |
C1i—C1—N1 | 105.8 (4) | C5i—C5—Cl4i | 113.1 (4) |
C2i—C1—C2 | 167.3 (19) | Cl5—C5—Cl4i | 8.0 (3) |
C1i—C1—C2 | 3.5 (7) | C3i—C6—C2i | 173 (6) |
C2i—C1—C6 | 41.5 (14) | C3i—C6—C5 | 56 (5) |
C1i—C1—C6 | 129.4 (8) | C2i—C6—C5 | 130.2 (13) |
C2i—C1—N2i | 57.5 (15) | C3i—C6—C1 | 168 (5) |
C1i—C1—N2i | 131.6 (3) | C2i—C6—C1 | 16.9 (7) |
N1—C1—N2i | 25.9 (2) | C3i—C6—C4i | 53 (5) |
C2—C1—N2i | 134.8 (5) | C2i—C6—C4i | 133.0 (11) |
C6—C1—N2i | 98.9 (9) | C5—C6—C4i | 3.2 (9) |
C2i—C1—C3i | 43.6 (12) | C1—C6—C4i | 116.1 (10) |
C1i—C1—C3i | 127.4 (6) | N2i—N1—O2i | 128.7 (8) |
N1—C1—C3i | 126.8 (8) | N2i—N1—O1 | 42.2 (5) |
C2—C1—C3i | 124.3 (9) | O2i—N1—O1 | 87.3 (4) |
C6—C1—C3i | 2.3 (11) | N2i—N1—C1 | 95.0 (8) |
N2i—C1—C3i | 101.0 (7) | O2i—N1—C1 | 135.5 (6) |
C2i—C1—N1i | 144.1 (16) | N2i—N1—C2i | 74.5 (7) |
C1i—C1—N1i | 44.8 (3) | O2i—N1—C2i | 155.5 (6) |
N1—C1—N1i | 61.0 (4) | O1—N1—C2i | 116.6 (5) |
C2—C1—N1i | 47.9 (3) | C1—N1—C2i | 20.5 (6) |
C6—C1—N1i | 174.0 (10) | N2i—N1—O2 | 159.5 (7) |
N2i—C1—N1i | 86.8 (3) | O2i—N1—O2 | 30.8 (3) |
C3i—C1—N1i | 172.1 (8) | C2i—N1—O2 | 125.6 (4) |
C1i—C2—C6i | 122 (2) | N2i—N1—N1i | 167.9 (7) |
C1i—C2—N2 | 105.1 (14) | O2i—N1—N1i | 61.5 (3) |
C6i—C2—N2 | 133.1 (10) | O1—N1—N1i | 148.8 (3) |
C1i—C2—N1i | 76.1 (12) | C1—N1—N1i | 74.2 (4) |
C6i—C2—N1i | 161.8 (11) | C2i—N1—N1i | 94.6 (3) |
N2—C2—N1i | 29.0 (2) | O2—N1—N1i | 31.0 (2) |
C1i—C2—C1 | 6.9 (15) | N2i—N1—C1i | 124.2 (8) |
C6i—C2—C1 | 115.7 (11) | O2i—N1—C1i | 106.2 (5) |
N1i—C2—C1 | 82.3 (4) | O1—N1—C1i | 166.4 (5) |
C1i—C2—C3 | 123.0 (17) | C1—N1—C1i | 29.4 (6) |
C6i—C2—C3 | 1.6 (13) | C2i—N1—C1i | 49.8 (3) |
N1i—C2—C3 | 160.3 (9) | O2—N1—C1i | 75.8 (4) |
C1i—C2—C2i | 9.5 (15) | N1i—N1—C1i | 44.8 (3) |
C6i—C2—C2i | 112.6 (9) | N1i—N2—O1i | 106.0 (8) |
N2—C2—C2i | 114.3 (3) | N1i—N2—C2 | 76.5 (7) |
N1i—C2—C2i | 85.3 (3) | O1i—N2—C2 | 175.1 (7) |
C1—C2—C2i | 3.2 (4) | N1i—N2—O2 | 28.8 (5) |
C3—C2—C2i | 114.0 (7) | O1i—N2—O2 | 77.9 (4) |
C6i—C3—C5i | 111 (5) | N1i—N2—C1i | 59.1 (6) |
C6i—C3—C4 | 116 (6) | O1i—N2—C1i | 164.6 (5) |
C5i—C3—C4 | 5.3 (11) | C2—N2—C1i | 17.4 (4) |
C6i—C3—C2 | 5 (5) | O2—N2—C1i | 87.6 (4) |
C5i—C3—C2 | 115.3 (8) | N2i—O1—N1 | 31.8 (3) |
C6i—C3—C1i | 10 (4) | N2i—O1—O2i | 67.0 (4) |
C5i—C3—C1i | 102.0 (8) | N1—O1—O2i | 35.5 (2) |
C4—C3—C1i | 107.0 (10) | O2i—O2—N1i | 118.0 (3) |
C2—C3—C1i | 13.4 (6) | O2i—O2—N2 | 140.5 (2) |
C5i—C4—C3 | 32 (5) | N1i—O2—N2 | 22.5 (3) |
C5i—C4—C4i | 95 (5) | O2i—O2—N1 | 31.2 (2) |
C3—C4—C4i | 125.6 (6) | N1i—O2—N1 | 87.5 (4) |
C5i—C4—C5 | 88 (6) | O2i—O2—O1i | 171.7 (5) |
C4i—C4—C5 | 8.2 (12) | N1i—O2—O1i | 57.2 (3) |
C5i—C4—C6i | 21 (5) | N2—O2—O1i | 35.1 (2) |
C3—C4—C6i | 11.3 (5) | N1—O2—O1i | 144.7 (3) |
C4i—C4—C6i | 114.3 (5) | Cl5i—Cl4—C4 | 56 (3) |
C5—C4—C6i | 106.4 (15) | Cl5i—Cl4—C5i | 53 (3) |
C5i—C4—Cl5i | 138 (6) | C4—Cl4—C5i | 3.5 (7) |
C3—C4—Cl5i | 109.4 (7) | Cl4i—Cl5—C4i | 114 (4) |
C4i—C4—Cl5i | 124.9 (5) | Cl4i—Cl5—C5 | 119 (4) |
C5—C4—Cl5i | 132.9 (17) | C4i—Cl5—C5 | 4.7 (8) |
Symmetry code: (i) −x+1, y, −z+3/2. |
(Crt) 5,6-dichlorobenzfurazan-1-oxide'
top
Crystal data top
C6H2Cl2N2O2 | F(000) = 408 |
Mr = 205.00 | Dx = 1.784 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.293 (5) Å | Cell parameters from 25 reflections |
b = 9.061 (6) Å | θ = 14–22° |
c = 11.618 (2) Å | µ = 0.80 mm−1 |
β = 96.12 (3)° | T = 297 K |
V = 763.4 (12) Å3 | Thin plate, colorless |
Z = 4 | 0.45 × 0.25 × 0.01 mm |
Data collection top
CAD-4 diffractometer | 472 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.079 |
Graphite monochromator | θmax = 26°, θmin = 3.5° |
ω–2θ scans | h = −8→8 |
Absorption correction: psi scan North, A. C. T., Phillips, D. C., and Mathews, F. S. (1968).
Acta Cryst., A24, 351-359. | k = 0→11 |
Tmin = 0.82, Tmax = 0.99 | l = −14→14 |
1588 measured reflections | 3 standard reflections every 60 min |
747 independent reflections | intensity decay: <1 |
Refinement top
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.136 | Idealized positions |
S = 0.83 | Calculated w = 1/[σ2(Fo2) + (0.055P)2 + 1.03P] where P = (Fo2 + 2Fc2)/3 |
747 reflections | (Δ/σ)max = 0.01 |
109 parameters | Δρmax = 0.18 e Å−3 |
33 restraints | Δρmin = −0.15 e Å−3 |
Crystal data top
C6H2Cl2N2O2 | V = 763.4 (12) Å3 |
Mr = 205.00 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 7.293 (5) Å | µ = 0.80 mm−1 |
b = 9.061 (6) Å | T = 297 K |
c = 11.618 (2) Å | 0.45 × 0.25 × 0.01 mm |
β = 96.12 (3)° | |
Data collection top
CAD-4 diffractometer | 472 reflections with I > 2σ(I) |
Absorption correction: psi scan North, A. C. T., Phillips, D. C., and Mathews, F. S. (1968).
Acta Cryst., A24, 351-359. | Rint = 0.079 |
Tmin = 0.82, Tmax = 0.99 | 3 standard reflections every 60 min |
1588 measured reflections | intensity decay: <1 |
747 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.038 | 33 restraints |
wR(F2) = 0.136 | Idealized positions |
S = 0.83 | Δρmax = 0.18 e Å−3 |
747 reflections | Δρmin = −0.15 e Å−3 |
109 parameters | |
Special details top
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 on F2 for ALL reflections except for 0 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.535 (3) | 0.2740 (11) | 0.7874 (15) | 0.054 (4) | 0.50 |
C2 | 0.437 (3) | 0.2859 (12) | 0.6764 (13) | 0.054 (3) | 0.50 |
C3 | 0.395 (2) | 0.4255 (16) | 0.6285 (13) | 0.0573 (15) | 0.50 |
H3 | 0.3439 | 0.4346 | 0.5538 | 0.069* | 0.50 |
C4 | 0.457 (3) | 0.5450 (15) | 0.6886 (17) | 0.054 (2) | 0.50 |
C5 | 0.556 (3) | 0.5292 (17) | 0.8047 (18) | 0.054 (2) | 0.50 |
C6 | 0.592 (2) | 0.3975 (15) | 0.8548 (14) | 0.0574 (15) | 0.50 |
H6 | 0.6804 | 0.3901 | 0.9234 | 0.069* | 0.50 |
N1 | 0.5541 (13) | 0.1340 (9) | 0.8151 (7) | 0.066 (2) | 0.50 |
N2 | 0.3910 (12) | 0.1506 (10) | 0.6337 (7) | 0.067 (2) | 0.50 |
O1 | 0.6284 (10) | 0.0649 (8) | 0.8975 (6) | 0.090 (2) | 0.50 |
O2 | 0.4666 (11) | 0.0539 (7) | 0.7170 (5) | 0.077 (2) | 0.50 |
Cl4 | 0.4143 (12) | 0.7193 (10) | 0.6324 (7) | 0.0662 (10) | 0.50 |
Cl5 | 0.6147 (12) | 0.6891 (10) | 0.8805 (6) | 0.0642 (9) | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.059 (6) | 0.062 (3) | 0.043 (11) | −0.015 (4) | 0.009 (6) | 0.000 (3) |
C2 | 0.059 (6) | 0.062 (3) | 0.043 (10) | −0.014 (4) | 0.008 (6) | 0.000 (3) |
C3 | 0.057 (3) | 0.065 (5) | 0.050 (4) | 0.003 (4) | 0.005 (3) | 0.000 (4) |
C4 | 0.049 (3) | 0.065 (3) | 0.049 (3) | −0.011 (5) | 0.009 (2) | −0.014 (5) |
C5 | 0.049 (3) | 0.065 (3) | 0.049 (3) | −0.011 (5) | 0.008 (2) | −0.015 (5) |
C6 | 0.057 (3) | 0.065 (5) | 0.050 (4) | 0.002 (4) | 0.005 (3) | −0.001 (4) |
N1 | 0.060 (5) | 0.077 (3) | 0.058 (5) | −0.005 (3) | −0.006 (3) | −0.002 (3) |
N2 | 0.061 (5) | 0.078 (3) | 0.060 (5) | −0.004 (3) | −0.005 (3) | −0.003 (3) |
O1 | 0.106 (5) | 0.072 (4) | 0.087 (4) | 0.004 (4) | −0.012 (4) | 0.024 (3) |
O2 | 0.084 (6) | 0.072 (3) | 0.074 (6) | −0.009 (4) | −0.001 (4) | −0.002 (3) |
Cl4 | 0.075 (2) | 0.062 (3) | 0.059 (2) | −0.0016 (13) | −0.004 (2) | 0.0006 (12) |
Cl5 | 0.073 (2) | 0.061 (3) | 0.057 (2) | −0.0059 (14) | −0.003 (2) | −0.0042 (13) |
Geometric parameters (Å, º) top
C1—N1 | 1.31 (2) | C4—Cl4 | 1.725 (4) |
C1—C6 | 1.403 (7) | C5—C6 | 1.341 (6) |
C1—C2 | 1.412 (11) | C5—Cl5 | 1.725 (4) |
C2—N2 | 1.35 (2) | N1—O1 | 1.221 (9) |
C2—C3 | 1.403 (7) | N1—O2 | 1.441 (8) |
C3—C4 | 1.341 (6) | N2—O2 | 1.376 (9) |
C4—C5 | 1.467 (8) | | |
| | | |
C1···C2i | 0.46 (3) | C6···C3i | 0.328 (12) |
C1···C1i | 0.96 (4) | C6···C2i | 1.09 (2) |
C1···N2i | 1.51 (2) | C6···C4i | 1.46 (3) |
C1···C3i | 1.73 (2) | N1···N2i | 0.697 (8) |
C1···N1i | 1.813 (12) | N1···O2i | 0.823 (7) |
C2···C1i | 0.46 (3) | N1···C2i | 1.381 (13) |
C2···C6i | 1.09 (2) | N1···N1i | 1.63 (2) |
C2···N1i | 1.381 (13) | N1···C1i | 1.813 (12) |
C2···C2i | 1.85 (3) | N2···N1i | 0.697 (8) |
C3···C6i | 0.328 (12) | N2···O1i | 0.863 (8) |
C3···C5i | 1.25 (4) | N2···C1i | 1.51 (2) |
C3···C1i | 1.73 (2) | O1···N2i | 0.863 (8) |
C4···C5i | 0.19 (3) | O1···O2i | 1.436 (9) |
C4···C6i | 1.46 (3) | O2···N1i | 0.823 (7) |
C4···C4i | 1.49 (3) | O2···O2i | 0.863 (10) |
C4···Cl5i | 1.59 (2) | O2···O1i | 1.436 (9) |
C5···C4i | 0.19 (3) | Cl4···Cl5i | 0.368 (8) |
C5···C3i | 1.25 (4) | Cl4···C5i | 1.87 (2) |
C5···C5i | 1.44 (4) | Cl5···Cl4i | 0.368 (8) |
C5···Cl4i | 1.87 (2) | Cl5···C4i | 1.59 (2) |
| | | |
N1—C1—C6 | 128.1 (17) | C4i—C4—Cl5i | 124.3 (8) |
N1—C1—C2 | 109.1 (8) | C5i—C4—Cl4 | 138 (10) |
C6—C1—C2 | 122.7 (16) | C6i—C4—Cl4 | 132.7 (14) |
N2—C2—C3 | 129.7 (14) | C4i—C4—Cl4 | 113.7 (6) |
N2—C2—C1 | 110.3 (8) | Cl5i—C4—Cl4 | 11.9 (3) |
C3—C2—C1 | 120.0 (15) | C4i—C5—C3i | 116 (10) |
C4—C3—C2 | 118.3 (12) | C4i—C5—C6 | 125 (10) |
C3—C4—C5 | 120.4 (14) | C3i—C5—C6 | 13.9 (6) |
C3—C4—Cl4 | 120.2 (10) | C4i—C5—C5i | 95 (10) |
C5—C4—Cl4 | 119.3 (16) | C3i—C5—C5i | 130.5 (8) |
C6—C5—C4 | 122.7 (14) | C6—C5—C5i | 116.8 (7) |
C6—C5—Cl5 | 120.0 (10) | C4i—C5—C4 | 94 (10) |
C5—C6—C1 | 115.7 (13) | C3i—C5—C4 | 136.6 (14) |
C4—C5—Cl5 | 117.2 (17) | C5i—C5—C4 | 7.6 (13) |
O1—N1—C1 | 135.6 (11) | C4i—C5—Cl5 | 44 (10) |
O1—N1—O2 | 118.9 (6) | C3i—C5—Cl5 | 106.0 (11) |
C1—N1—O2 | 105.5 (9) | C5i—C5—Cl5 | 122.6 (7) |
C2—N2—O2 | 104.8 (8) | C4i—C5—Cl4i | 38 (10) |
N2—O2—N1 | 110.2 (6) | C3i—C5—Cl4i | 115.9 (12) |
C2i—C1—C1i | 166 (4) | C6—C5—Cl4i | 129.8 (11) |
C2i—C1—N1 | 89 (4) | C5i—C5—Cl4i | 112.1 (7) |
C1i—C1—N1 | 104.7 (8) | C4—C5—Cl4i | 107.1 (15) |
C2i—C1—C6 | 39 (3) | Cl5—C5—Cl4i | 10.7 (4) |
C1i—C1—C6 | 127.1 (12) | C3i—C6—C2i | 162 (7) |
C2i—C1—C2 | 162 (4) | C3i—C6—C5 | 66 (7) |
C1i—C1—C2 | 4.7 (10) | C2i—C6—C5 | 131.3 (14) |
C2i—C1—N2i | 62 (3) | C3i—C6—C1 | 178 (7) |
C1i—C1—N2i | 132.1 (5) | C2i—C6—C1 | 15.6 (15) |
N1—C1—N2i | 27.5 (5) | C3i—C6—C4i | 63 (6) |
C6—C1—N2i | 100.8 (15) | C2i—C6—C4i | 134.7 (19) |
C2—C1—N2i | 136.5 (8) | C5—C6—C4i | 6.3 (18) |
C2i—C1—C3i | 39 (3) | C1—C6—C4i | 119.3 (18) |
C1i—C1—C3i | 127.4 (8) | N2i—N1—O2i | 129.7 (15) |
N1—C1—C3i | 127.7 (14) | N2i—N1—O1 | 43.6 (9) |
C6—C1—C3i | 0.4 (13) | O2i—N1—O1 | 87.0 (8) |
C2—C1—C3i | 123.1 (15) | N2i—N1—C1 | 92.0 (14) |
N2i—C1—C3i | 100.4 (11) | O2i—N1—C1 | 137.1 (12) |
C2i—C1—N1i | 149 (4) | N2i—N1—C2i | 72.8 (13) |
C1i—C1—N1i | 44.5 (6) | O2i—N1—C2i | 156.5 (12) |
N1—C1—N1i | 60.4 (7) | O1—N1—C2i | 116.2 (10) |
C6—C1—N1i | 171.5 (16) | C1—N1—C2i | 19.5 (12) |
C2—C1—N1i | 48.8 (5) | N2i—N1—O2 | 161.6 (13) |
N2i—C1—N1i | 87.7 (6) | O2i—N1—O2 | 32.1 (6) |
C3i—C1—N1i | 171.9 (13) | C2i—N1—O2 | 124.9 (8) |
C1i—C2—C6i | 125 (4) | N2i—N1—N1i | 165.7 (14) |
C1i—C2—N2 | 101 (3) | O2i—N1—N1i | 62.1 (7) |
C6i—C2—N2 | 133.6 (15) | O1—N1—N1i | 149.1 (6) |
C1i—C2—N1i | 72 (3) | C1—N1—N1i | 75.2 (8) |
C6i—C2—N1i | 163.1 (17) | C2i—N1—N1i | 94.7 (7) |
N2—C2—N1i | 29.5 (5) | O2—N1—N1i | 30.3 (3) |
C1i—C2—C3 | 129 (4) | N2i—N1—C1i | 122.9 (14) |
C6i—C2—C3 | 4.0 (17) | O2i—N1—C1i | 106.5 (10) |
N1i—C2—C3 | 159.1 (15) | O1—N1—C1i | 166.4 (10) |
C1i—C2—C1 | 10 (3) | C1—N1—C1i | 30.9 (12) |
C6i—C2—C1 | 116.0 (18) | C2i—N1—C1i | 50.3 (4) |
N1i—C2—C1 | 80.9 (7) | O2—N1—C1i | 74.7 (7) |
C1i—C2—C2i | 14 (3) | N1i—N1—C1i | 44.4 (6) |
C6i—C2—C2i | 111.6 (12) | N1i—N2—O1i | 102.6 (14) |
N2—C2—C2i | 114.7 (6) | N1i—N2—C2 | 77.7 (12) |
N1i—C2—C2i | 85.3 (7) | O1i—N2—C2 | 174.1 (14) |
C3—C2—C2i | 115.6 (10) | N1i—N2—O2 | 27.4 (9) |
C1—C2—C2i | 4.5 (8) | O1i—N2—O2 | 75.9 (8) |
C6i—C3—C5i | 100 (7) | N1i—N2—C1i | 60.4 (11) |
C6i—C3—C4 | 105 (6) | O1i—N2—C1i | 162.8 (11) |
C5i—C3—C4 | 7.5 (17) | C2—N2—C1i | 17.4 (8) |
C6i—C3—C2 | 14 (6) | O2—N2—C1i | 87.4 (7) |
C5i—C3—C2 | 113.4 (13) | N2i—O1—N1 | 33.8 (6) |
C6i—C3—C1i | 2 (6) | N2i—O1—O2i | 68.4 (7) |
C5i—C3—C1i | 101.5 (12) | N1—O1—O2i | 34.9 (4) |
C4—C3—C1i | 106.4 (11) | N1i—O2—O2i | 117.5 (8) |
C2—C3—C1i | 11.9 (12) | N1i—O2—N2 | 22.9 (7) |
C5i—C4—C3 | 57 (10) | O2i—O2—N2 | 140.3 (5) |
C5i—C4—C6i | 49 (10) | N1i—O2—O1i | 58.1 (7) |
C3—C4—C6i | 12.5 (8) | O2i—O2—O1i | 173.3 (12) |
C5i—C4—C5 | 77 (10) | N2—O2—O1i | 35.6 (4) |
C6i—C4—C5 | 107.9 (10) | N1i—O2—N1 | 87.6 (10) |
C5i—C4—C4i | 78 (10) | O2i—O2—N1 | 30.4 (3) |
C3—C4—C4i | 125.5 (7) | O1i—O2—N1 | 145.7 (6) |
C6i—C4—C4i | 113.1 (9) | Cl5i—Cl4—C4 | 63 (4) |
C5—C4—C4i | 7.5 (12) | Cl5i—Cl4—C5i | 61 (3) |
C5i—C4—Cl5i | 131 (10) | C4—Cl4—C5i | 3.9 (15) |
C3—C4—Cl5i | 108.9 (11) | Cl4i—Cl5—C4i | 105 (4) |
C6i—C4—Cl5i | 121.3 (14) | Cl4i—Cl5—C5 | 109 (4) |
C5—C4—Cl5i | 130.3 (16) | C4i—Cl5—C5 | 4.9 (15) |
Symmetry code: (i) −x+1, y, −z+3/2. |
Crystal data top
C8H2Cl2O3 | F(000) = 432 |
Mr = 217.00 | Dx = 1.803 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.987 (4) Å | Cell parameters from 49 reflections |
b = 8.994 (3) Å | θ = 11–29° |
c = 7.423 (4) Å | µ = 0.77 mm−1 |
β = 92.91 (4)° | T = 297 K |
V = 799.2 (6) Å3 | Thick needle, colorless |
Z = 4 | 0.45 × 0.25 × 0.15 mm |
Data collection top
CAD-4 diffractometer | 1041 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.015 |
Graphite monochromator | θmax = 30°, θmin = 2.8° |
ω scans | h = −16→16 |
Absorption correction: ψ scan North, A. C. T., Phillips, D. C., and Mathews, F. S. (1968).
Acta Cryst., A24, 351-359. | k = 0→12 |
Tmin = 0.76, Tmax = 0.89 | l = −10→10 |
2336 measured reflections | 3 standard reflections every 50 min |
1171 independent reflections | intensity decay: <1% |
Refinement top
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)] = 0.029 | Not refined, put in idealized positions |
wR(F2) = 0.085 | Calculated w = 1/[σ2(Fo2) + (0.036P)2 + 0.23P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.01 |
1171 reflections | Δρmax = 0.43 e Å−3 |
61 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.146 (7) |
Crystal data top
C8H2Cl2O3 | V = 799.2 (6) Å3 |
Mr = 217.00 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 11.987 (4) Å | µ = 0.77 mm−1 |
b = 8.994 (3) Å | T = 297 K |
c = 7.423 (4) Å | 0.45 × 0.25 × 0.15 mm |
β = 92.91 (4)° | |
Data collection top
CAD-4 diffractometer | 1041 reflections with I > 2σ(I) |
Absorption correction: ψ scan North, A. C. T., Phillips, D. C., and Mathews, F. S. (1968).
Acta Cryst., A24, 351-359. | Rint = 0.015 |
Tmin = 0.76, Tmax = 0.89 | 3 standard reflections every 50 min |
2336 measured reflections | intensity decay: <1% |
1171 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.029 | 0 restraints |
wR(F2) = 0.085 | Not refined, put in idealized positions |
S = 1.06 | Δρmax = 0.43 e Å−3 |
1171 reflections | Δρmin = −0.18 e Å−3 |
61 parameters | |
Special details top
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 on F2 for ALL reflections except for 0 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.55276 (9) | 0.24651 (14) | 0.2933 (2) | 0.0378 (3) | |
C5 | 0.55436 (10) | 0.50873 (14) | 0.2914 (2) | 0.0384 (3) | |
C6 | 0.60860 (9) | 0.3765 (2) | 0.3361 (2) | 0.0403 (3) | |
H6 | 0.67966 (9) | 0.3757 (2) | 0.3926 (2) | 0.048* | |
C7 | 0.58546 (11) | 0.0907 (2) | 0.3254 (2) | 0.0461 (3) | |
O1 | 0.66550 (9) | 0.03635 (13) | 0.4008 (2) | 0.0646 (4) | |
O2 | 0.5000 | 0.0016 (2) | 0.2500 | 0.0565 (4) | |
Cl5 | 0.62077 (3) | 0.67439 (4) | 0.33897 (5) | 0.0508 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0330 (5) | 0.0360 (6) | 0.0438 (6) | 0.0011 (4) | −0.0044 (4) | 0.0015 (4) |
C5 | 0.0386 (6) | 0.0363 (6) | 0.0399 (6) | −0.0035 (4) | −0.0005 (4) | −0.0013 (4) |
C6 | 0.0335 (5) | 0.0410 (7) | 0.0455 (6) | −0.0022 (4) | −0.0063 (4) | −0.0001 (5) |
C7 | 0.0357 (6) | 0.0384 (6) | 0.0632 (8) | −0.0001 (5) | −0.0082 (5) | 0.0031 (5) |
O1 | 0.0467 (6) | 0.0461 (6) | 0.0983 (9) | 0.0035 (5) | −0.0240 (6) | 0.0096 (6) |
O2 | 0.0408 (7) | 0.0348 (6) | 0.0920 (11) | 0.000 | −0.0150 (7) | 0.000 |
Cl5 | 0.0513 (2) | 0.0386 (2) | 0.0622 (3) | −0.00844 (12) | −0.00183 (15) | −0.00561 (13) |
Geometric parameters (Å, º) top
C1—C6 | 1.376 (2) | C5—Cl5 | 1.7176 (13) |
C1—C1i | 1.389 (2) | C7—O1 | 1.191 (2) |
C1—C7 | 1.471 (2) | C7—O2 | 1.395 (2) |
C5—C6 | 1.388 (2) | O2—C7i | 1.395 (2) |
C5—C5i | 1.412 (3) | | |
| | | |
C6—C1—C1i | 121.83 (7) | C1—C6—C5 | 117.15 (10) |
C6—C1—C7 | 130.49 (11) | O1—C7—O2 | 120.69 (14) |
C1i—C1—C7 | 107.68 (7) | O1—C7—C1 | 131.96 (13) |
C6—C5—C5i | 120.99 (7) | O2—C7—C1 | 107.34 (11) |
C6—C5—Cl5 | 119.19 (10) | C7i—O2—C7 | 109.9 (2) |
C5i—C5—Cl5 | 119.82 (5) | | |
Symmetry code: (i) −x+1, y, −z+1/2. |
Crystal data top
C8H2Br2O3 | Z = 4 |
Mr = 305.92 | F(000) = 576 |
Triclinic, C1 | Dx = 2.364 Mg m−3 |
a = 12.923 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.209 (2) Å | Cell parameters from 25 reflections |
c = 7.6280 (15) Å | θ = 13–22° |
α = 105.08 (3)° | µ = 9.40 mm−1 |
β = 99.20 (3)° | T = 297 K |
γ = 81.29 (3)° | Plate, colorless |
V = 859.5 (3) Å3 | 0.35 × 0.20 × 0.07 mm |
Data collection top
CAD-4 diffractometer | 1284 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.050 |
Graphite monochromator | θmax = 28°, θmin = 2.7° |
ω–2θ scans | h = −16→16 |
Absorption correction: ψ scan North, A. C. T., Phillips, D. C., and Mathews, F. S. (1968).
Acta Cryst., A24, 351-359. | k = −12→12 |
Tmin = 0.23, Tmax = 0.52 | l = −10→10 |
4009 measured reflections | 3 standard reflections every 60 min |
2058 independent reflections | intensity decay: <1% |
Refinement top
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)] = 0.050 | Idealized positions |
wR(F2) = 0.139 | Calculated w = 1/[σ2(Fo2) + (0.064P)2 + 0.18P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.01 |
2057 reflections | Δρmax = 0.80 e Å−3 |
119 parameters | Δρmin = −0.74 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0047 (9) |
Crystal data top
C8H2Br2O3 | γ = 81.29 (3)° |
Mr = 305.92 | V = 859.5 (3) Å3 |
Triclinic, C1 | Z = 4 |
a = 12.923 (3) Å | Mo Kα radiation |
b = 9.209 (2) Å | µ = 9.40 mm−1 |
c = 7.6280 (15) Å | T = 297 K |
α = 105.08 (3)° | 0.35 × 0.20 × 0.07 mm |
β = 99.20 (3)° | |
Data collection top
CAD-4 diffractometer | 1284 reflections with I > 2σ(I) |
Absorption correction: ψ scan North, A. C. T., Phillips, D. C., and Mathews, F. S. (1968).
Acta Cryst., A24, 351-359. | Rint = 0.050 |
Tmin = 0.23, Tmax = 0.52 | 3 standard reflections every 60 min |
4009 measured reflections | intensity decay: <1% |
2058 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.139 | Idealized positions |
S = 1.03 | Δρmax = 0.80 e Å−3 |
2057 reflections | Δρmin = −0.74 e Å−3 |
119 parameters | |
Special details top
Experimental. The space group is C-1 for reasons explained in the text. When checkcif reads
the file it changes the C-1 to P-1, which is incorrect. |
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 on F2 for ALL reflections except for 1 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.5553 (5) | 0.2655 (8) | 0.2842 (9) | 0.0378 (14) | |
C2 | 0.4529 (5) | 0.2683 (8) | 0.1995 (10) | 0.0399 (15) | |
C3 | 0.3955 (5) | 0.3988 (8) | 0.1619 (9) | 0.0368 (14) | |
H3 | 0.3259 (5) | 0.4010 (8) | 0.1070 (9) | 0.044* | |
C4 | 0.4498 (5) | 0.5276 (7) | 0.2125 (9) | 0.0377 (14) | |
C5 | 0.5523 (5) | 0.5250 (7) | 0.2963 (10) | 0.0382 (14) | |
C6 | 0.6090 (5) | 0.3925 (7) | 0.3352 (9) | 0.0356 (13) | |
H6 | 0.6783 (5) | 0.3898 (7) | 0.3918 (9) | 0.043* | |
C7 | 0.5912 (6) | 0.1096 (8) | 0.3068 (11) | 0.044 (2) | |
C8 | 0.4208 (6) | 0.1150 (8) | 0.1613 (11) | 0.044 (2) | |
O1 | 0.6722 (5) | 0.0542 (6) | 0.3695 (9) | 0.063 (2) | |
O2 | 0.5069 (4) | 0.0238 (5) | 0.2304 (8) | 0.0509 (13) | |
O3 | 0.3416 (5) | 0.0645 (6) | 0.0907 (9) | 0.061 (2) | |
Br4 | 0.37379 (6) | 0.70771 (8) | 0.16374 (12) | 0.0508 (3) | |
Br5 | 0.62425 (6) | 0.69818 (9) | 0.35590 (12) | 0.0518 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.031 (3) | 0.043 (3) | 0.038 (4) | −0.004 (3) | −0.005 (3) | 0.013 (3) |
C2 | 0.036 (4) | 0.044 (3) | 0.039 (4) | −0.002 (3) | 0.005 (3) | 0.011 (3) |
C3 | 0.027 (3) | 0.045 (3) | 0.036 (3) | −0.005 (2) | −0.004 (3) | 0.009 (3) |
C4 | 0.038 (4) | 0.035 (3) | 0.040 (4) | 0.002 (3) | 0.004 (3) | 0.013 (3) |
C5 | 0.039 (4) | 0.038 (3) | 0.036 (4) | −0.008 (3) | −0.001 (3) | 0.008 (3) |
C6 | 0.027 (3) | 0.038 (3) | 0.039 (4) | −0.004 (2) | −0.002 (3) | 0.007 (3) |
C7 | 0.045 (4) | 0.038 (3) | 0.047 (4) | −0.006 (3) | 0.000 (3) | 0.010 (3) |
C8 | 0.035 (4) | 0.042 (3) | 0.052 (5) | −0.004 (3) | 0.002 (3) | 0.011 (3) |
O1 | 0.050 (3) | 0.050 (3) | 0.081 (4) | 0.001 (2) | −0.020 (3) | 0.024 (3) |
O2 | 0.040 (3) | 0.037 (2) | 0.068 (4) | −0.006 (2) | −0.013 (3) | 0.012 (2) |
O3 | 0.045 (3) | 0.052 (3) | 0.082 (4) | −0.018 (2) | −0.017 (3) | 0.019 (3) |
Br4 | 0.0495 (5) | 0.0434 (4) | 0.0597 (6) | 0.0052 (3) | 0.0031 (4) | 0.0211 (4) |
Br5 | 0.0517 (5) | 0.0473 (4) | 0.0586 (5) | −0.0184 (3) | 0.0002 (4) | 0.0137 (3) |
Geometric parameters (Å, º) top
C1—C2 | 1.376 (9) | C4—Br4 | 1.888 (6) |
C1—C6 | 1.386 (9) | C5—C6 | 1.401 (9) |
C1—C7 | 1.486 (9) | C5—Br5 | 1.885 (7) |
C2—C3 | 1.385 (9) | C7—O1 | 1.179 (9) |
C2—C8 | 1.476 (10) | C7—O2 | 1.403 (9) |
C3—C4 | 1.405 (9) | C8—O3 | 1.179 (9) |
C4—C5 | 1.376 (9) | C8—O2 | 1.408 (8) |
| | | |
C2—C1—C6 | 122.4 (6) | C4—C5—Br5 | 121.3 (5) |
C2—C1—C7 | 108.0 (6) | C6—C5—Br5 | 117.1 (5) |
C6—C1—C7 | 129.6 (6) | C1—C6—C5 | 115.9 (6) |
C1—C2—C3 | 122.4 (7) | O1—C7—O2 | 121.2 (6) |
C1—C2—C8 | 108.5 (6) | O1—C7—C1 | 132.1 (7) |
C3—C2—C8 | 129.1 (7) | O2—C7—C1 | 106.8 (6) |
C2—C3—C4 | 115.4 (6) | O3—C8—O2 | 120.9 (7) |
C5—C4—C3 | 122.3 (6) | O3—C8—C2 | 132.3 (7) |
C5—C4—Br4 | 121.1 (5) | O2—C8—C2 | 106.8 (6) |
C3—C4—Br4 | 116.6 (5) | C7—O2—C8 | 110.0 (5) |
C4—C5—C6 | 121.6 (6) | | |
Experimental details
| (Alt) | (Art) | (Blt) | (Brt) |
Crystal data |
Chemical formula | C6H2Cl2N2O2 | C6H2Cl2N2O2 | C6H2Cl2N2O2 | C6H2Cl2N2O2 |
Mr | 205.00 | 205.00 | 205.00 | 205.00 |
Crystal system, space group | Monoclinic, C2/c | Monoclinic, C2/c | Monoclinic, P21/n | Monoclinic, P21/n |
Temperature (K) | 173 | 297 | 173 | 297 |
a, b, c (Å) | 11.397 (2), 8.871 (2), 7.222 (4) | 11.554 (2), 8.926 (2), 7.310 (6) | 7.0679 (6), 11.7502 (9), 9.0114 (7) | 7.1739 (2), 11.8351 (2), 9.0639 (1) |
α, β, γ (°) | 90, 95.12 (3), 90 | 90, 96.10 (4), 90 | 90, 98.563 (1), 90 | 90, 98.350 (1), 90 |
V (Å3) | 727.3 (5) | 749.6 (7) | 740.05 (10) | 761.40 (3) |
Z | 4 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.84 | 0.82 | 0.83 | 0.80 |
Crystal size (mm) | 0.50 × 0.28 × 0.12 | 0.50 × 0.28 × 0.12 | 0.5 × 0.35 × 0.3 | 0.50 × 0.35 × 0.30 |
|
Data collection |
Diffractometer | CAD-4 diffractometer | CAD-4 diffractometer | SMART diffractometer | SMART diffractometer |
Absorption correction | Psi scan North, A. C. T., Phillips, D. C., and Mathews, F. S. (1968).
Acta Cryst., A24, 351-359. | Psi scan North, A. C. T., Phillips, D. C., and Mathews, F. S. (1968).
Acta Cryst., A24, 351-359. | SADABS (Sheldrick,1996) | SADABS (Sheldrick,1996) |
Tmin, Tmax | 0.74, 0.90 | 0.74, 0.90 | 0.63, 0.81 | 0.47, 0.82 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2528, 1267, 1140 | 1811, 908, 780 | 3699, 1305, 1145 | 3751, 1330, 1158 |
Rint | 0.026 | 0.024 | 0.016 | 0.015 |
(sin θ/λ)max (Å−1) | 0.746 | 0.661 | 0.595 | 0.595 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.076, 1.13 | 0.035, 0.085, 1.09 | 0.038, 0.110, 1.04 | 0.036, 0.107, 1.73 |
No. of reflections | 1267 | 908 | 1305 | 1330 |
No. of parameters | 110 | 110 | 218 | 218 |
No. of restraints | 33 | 33 | 113 | 113 |
H-atom treatment | Idealized positions | Idealized positions | Idealized positions | Idealized positions |
Δρmax, Δρmin (e Å−3) | 0.47, −0.35 | 0.37, −0.21 | 0.47, −0.50 | 0.37, −0.31 |
| (Clt) | (Crt) | (CPA) | (BPA) |
Crystal data |
Chemical formula | C6H2Cl2N2O2 | C6H2Cl2N2O2 | C8H2Cl2O3 | C8H2Br2O3 |
Mr | 205.00 | 205.00 | 217.00 | 305.92 |
Crystal system, space group | Monoclinic, C2/c | Monoclinic, C2/c | Monoclinic, C2/c | Triclinic, C1 |
Temperature (K) | 173 | 297 | 297 | 297 |
a, b, c (Å) | 7.2233 (1), 9.0549 (3), 11.5700 (4) | 7.293 (5), 9.061 (6), 11.618 (2) | 11.987 (4), 8.994 (3), 7.423 (4) | 12.923 (3), 9.209 (2), 7.6280 (15) |
α, β, γ (°) | 90, 95.315 (2), 90 | 90, 96.12 (3), 90 | 90, 92.91 (4), 90 | 105.08 (3), 99.20 (3), 81.29 (3) |
V (Å3) | 753.50 (4) | 763.4 (12) | 799.2 (6) | 859.5 (3) |
Z | 4 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.81 | 0.80 | 0.77 | 9.40 |
Crystal size (mm) | 0.50 × 0.45 × 0.20 | 0.45 × 0.25 × 0.01 | 0.45 × 0.25 × 0.15 | 0.35 × 0.20 × 0.07 |
|
Data collection |
Diffractometer | SMART diffractometer | CAD-4 diffractometer | CAD-4 diffractometer | CAD-4 diffractometer |
Absorption correction | SADABS (Sheldrick,1996) | Psi scan North, A. C. T., Phillips, D. C., and Mathews, F. S. (1968).
Acta Cryst., A24, 351-359. | ψ scan North, A. C. T., Phillips, D. C., and Mathews, F. S. (1968).
Acta Cryst., A24, 351-359. | ψ scan North, A. C. T., Phillips, D. C., and Mathews, F. S. (1968).
Acta Cryst., A24, 351-359. |
Tmin, Tmax | 0.67, 0.85 | 0.82, 0.99 | 0.76, 0.89 | 0.23, 0.52 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3292, 659, 594 | 1588, 747, 472 | 2336, 1171, 1041 | 4009, 2058, 1284 |
Rint | 0.024 | 0.079 | 0.015 | 0.050 |
(sin θ/λ)max (Å−1) | 0.596 | 0.617 | 0.703 | 0.661 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.073, 1.12 | 0.038, 0.136, 0.83 | 0.029, 0.085, 1.06 | 0.050, 0.139, 1.03 |
No. of reflections | 659 | 747 | 1171 | 2057 |
No. of parameters | 109 | 109 | 61 | 119 |
No. of restraints | 33 | 33 | 0 | 0 |
H-atom treatment | Idealized positions | Idealized positions | Not refined, put in idealized positions | Idealized positions |
Δρmax, Δρmin (e Å−3) | 0.18, −0.21 | 0.18, −0.15 | 0.43, −0.18 | 0.80, −0.74 |
Selected geometric parameters (Å, º) for (CPA) topC1—C6 | 1.376 (2) | C5—Cl5 | 1.7176 (13) |
C1—C1i | 1.389 (2) | C7—O1 | 1.191 (2) |
C1—C7 | 1.471 (2) | C7—O2 | 1.395 (2) |
C5—C6 | 1.388 (2) | O2—C7i | 1.395 (2) |
C5—C5i | 1.412 (3) | | |
| | | |
C6—C1—C1i | 121.83 (7) | C1—C6—C5 | 117.15 (10) |
C6—C1—C7 | 130.49 (11) | O1—C7—O2 | 120.69 (14) |
C1i—C1—C7 | 107.68 (7) | O1—C7—C1 | 131.96 (13) |
C6—C5—C5i | 120.99 (7) | O2—C7—C1 | 107.34 (11) |
C6—C5—Cl5 | 119.19 (10) | C7i—O2—C7 | 109.9 (2) |
C5i—C5—Cl5 | 119.82 (5) | | |
Symmetry code: (i) −x+1, y, −z+1/2. |
Selected geometric parameters (Å, º) for (BPA) topC1—C2 | 1.376 (9) | C4—Br4 | 1.888 (6) |
C1—C6 | 1.386 (9) | C5—C6 | 1.401 (9) |
C1—C7 | 1.486 (9) | C5—Br5 | 1.885 (7) |
C2—C3 | 1.385 (9) | C7—O1 | 1.179 (9) |
C2—C8 | 1.476 (10) | C7—O2 | 1.403 (9) |
C3—C4 | 1.405 (9) | C8—O3 | 1.179 (9) |
C4—C5 | 1.376 (9) | C8—O2 | 1.408 (8) |
| | | |
C2—C1—C6 | 122.4 (6) | C4—C5—Br5 | 121.3 (5) |
C2—C1—C7 | 108.0 (6) | C6—C5—Br5 | 117.1 (5) |
C6—C1—C7 | 129.6 (6) | C1—C6—C5 | 115.9 (6) |
C1—C2—C3 | 122.4 (7) | O1—C7—O2 | 121.2 (6) |
C1—C2—C8 | 108.5 (6) | O1—C7—C1 | 132.1 (7) |
C3—C2—C8 | 129.1 (7) | O2—C7—C1 | 106.8 (6) |
C2—C3—C4 | 115.4 (6) | O3—C8—O2 | 120.9 (7) |
C5—C4—C3 | 122.3 (6) | O3—C8—C2 | 132.3 (7) |
C5—C4—Br4 | 121.1 (5) | O2—C8—C2 | 106.8 (6) |
C3—C4—Br4 | 116.6 (5) | C7—O2—C8 | 110.0 (5) |
C4—C5—C6 | 121.6 (6) | | |