The molecular structures of 4,7-dichlorobenzo[
c]furazan 1-oxide, C
6H
2Cl
2N
2O
2, (I), and 4,7-dibromobenzo[
c]furazan 1-oxide, C
6H
2Br
2N
2O
2, (II), are normal. Compound (I) occurs in two polymorphic forms. One polymorph contains one molecule in the asymmetric unit, organized into two-dimensional sheets involving intermolecular N
Cl and O
Cl interactions. The second polymorph has three molecules in the asymmetric unit, organized into two crystallographically different two-dimensional sheets with similar interactions. Compound (II) is isomorphous with the second polymorph of (I). The three two-dimensional sheets in the two polymorphs comprise a set of three two-dimensional polymorphic arrangements.
Supporting information
CCDC references: 184500; 184501; 184502
For all compounds, data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1995); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
(DCL-I) 4,7-dichlorobenzo[
c]furazan 1-oxide, polymorph I
top
Crystal data top
C6H2Cl2N2O2 | Z = 2 |
Mr = 205.00 | F(000) = 204 |
Triclinic, P1 | Dx = 1.812 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.357 (2) Å | Cell parameters from 2332 reflections |
b = 7.667 (2) Å | θ = 2.7–27.5° |
c = 8.190 (2) Å | µ = 0.82 mm−1 |
α = 92.10 (1)° | T = 173 K |
β = 109.81 (1)° | Prism, yellow |
γ = 117.31 (1)° | 0.3 × 0.3 × 0.1 mm |
V = 375.8 (2) Å3 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 1695 independent reflections |
Radiation source: fine-focus sealed tube | 1447 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
ω scans | θmax = 27.5°, θmin = 2.7° |
Absorption correction: multi-scan [SADABS; Sheldrick (1996) and Blessing (1995)] | h = −9→9 |
Tmin = 0.78, Tmax = 0.92 | k = −9→9 |
4117 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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | All H-atom parameters refined |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0591P)2 + 0.0163P] where P = (Fo2 + 2Fc2)/3 |
1695 reflections | (Δ/σ)max = 0.001 |
117 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl3 | 0.78094 (7) | 0.99930 (7) | 1.20464 (5) | 0.03031 (16) | |
Cl6 | 0.35870 (8) | 0.62810 (8) | 0.37792 (5) | 0.03238 (17) | |
O1 | 0.0421 (2) | 0.31621 (19) | 0.54816 (17) | 0.0342 (3) | |
O2 | 0.1670 (2) | 0.42708 (19) | 0.85108 (16) | 0.0291 (3) | |
N1 | 0.1871 (2) | 0.4513 (2) | 0.68087 (18) | 0.0239 (3) | |
N2 | 0.3423 (2) | 0.5925 (2) | 0.98315 (18) | 0.0254 (3) | |
C1 | 0.3702 (3) | 0.6289 (2) | 0.7162 (2) | 0.0194 (3) | |
C2 | 0.4622 (3) | 0.7114 (2) | 0.9024 (2) | 0.0193 (3) | |
C3 | 0.6620 (3) | 0.9018 (3) | 0.9777 (2) | 0.0215 (3) | |
C4 | 0.7545 (3) | 1.0000 (3) | 0.8672 (3) | 0.0266 (4) | |
H4 | 0.881 (3) | 1.132 (3) | 0.910 (3) | 0.028 (5)* | |
C5 | 0.6581 (3) | 0.9150 (3) | 0.6790 (2) | 0.0265 (4) | |
H5 | 0.727 (4) | 0.983 (3) | 0.610 (3) | 0.037 (6)* | |
C6 | 0.4705 (3) | 0.7324 (3) | 0.6025 (2) | 0.0226 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl3 | 0.0272 (3) | 0.0321 (3) | 0.0221 (2) | 0.0123 (2) | 0.00398 (18) | −0.00301 (18) |
Cl6 | 0.0452 (3) | 0.0417 (3) | 0.0188 (2) | 0.0263 (2) | 0.0156 (2) | 0.0094 (2) |
O1 | 0.0330 (7) | 0.0239 (7) | 0.0235 (6) | 0.0031 (6) | 0.0038 (5) | −0.0036 (5) |
O2 | 0.0281 (7) | 0.0229 (6) | 0.0246 (6) | 0.0021 (5) | 0.0129 (5) | 0.0068 (5) |
N1 | 0.0252 (7) | 0.0201 (7) | 0.0197 (7) | 0.0068 (6) | 0.0081 (6) | 0.0038 (6) |
N2 | 0.0254 (7) | 0.0250 (8) | 0.0197 (7) | 0.0067 (6) | 0.0106 (6) | 0.0050 (6) |
C1 | 0.0205 (8) | 0.0183 (8) | 0.0182 (7) | 0.0087 (7) | 0.0081 (6) | 0.0042 (6) |
C2 | 0.0202 (8) | 0.0202 (8) | 0.0194 (8) | 0.0104 (7) | 0.0094 (6) | 0.0054 (6) |
C3 | 0.0188 (8) | 0.0204 (8) | 0.0213 (8) | 0.0085 (7) | 0.0060 (6) | 0.0026 (6) |
C4 | 0.0209 (8) | 0.0214 (9) | 0.0323 (9) | 0.0065 (7) | 0.0106 (7) | 0.0078 (7) |
C5 | 0.0267 (9) | 0.0298 (10) | 0.0304 (9) | 0.0141 (8) | 0.0186 (8) | 0.0161 (8) |
C6 | 0.0277 (9) | 0.0272 (9) | 0.0206 (8) | 0.0163 (7) | 0.0139 (7) | 0.0101 (7) |
Geometric parameters (Å, º) top
Cl3—C3 | 1.7250 (17) | C1—C6 | 1.422 (2) |
Cl6—C6 | 1.7214 (17) | C2—C3 | 1.422 (2) |
O1—N1 | 1.2287 (19) | C3—C4 | 1.359 (2) |
O2—N2 | 1.3764 (19) | C4—C5 | 1.437 (3) |
O2—N1 | 1.4604 (18) | C4—H4 | 0.95 (2) |
N1—C1 | 1.333 (2) | C5—C6 | 1.354 (3) |
N2—C2 | 1.322 (2) | C5—H5 | 0.91 (2) |
C1—C2 | 1.421 (2) | | |
| | | |
N2—O2—N1 | 109.32 (12) | C4—C3—Cl3 | 122.13 (14) |
O1—N1—C1 | 136.55 (15) | C2—C3—Cl3 | 119.50 (12) |
O1—N1—O2 | 117.61 (14) | C3—C4—C5 | 121.80 (17) |
C1—N1—O2 | 105.83 (12) | C3—C4—H4 | 121.2 (12) |
C2—N2—O2 | 105.49 (13) | C5—C4—H4 | 116.9 (12) |
N1—C1—C2 | 107.03 (14) | C6—C5—C4 | 121.71 (16) |
N1—C1—C6 | 131.03 (15) | C6—C5—H5 | 118.9 (14) |
C2—C1—C6 | 121.94 (15) | C4—C5—H5 | 119.3 (14) |
N2—C2—C1 | 112.33 (15) | C5—C6—C1 | 117.13 (15) |
N2—C2—C3 | 128.64 (15) | C5—C6—Cl6 | 121.67 (13) |
C1—C2—C3 | 119.03 (14) | C1—C6—Cl6 | 121.20 (14) |
C4—C3—C2 | 118.37 (15) | | |
| | | |
N2—O2—N1—O1 | −179.67 (15) | N2—C2—C3—C4 | −178.56 (18) |
N2—O2—N1—C1 | −0.56 (17) | C1—C2—C3—C4 | 1.6 (2) |
N1—O2—N2—C2 | 0.27 (17) | N2—C2—C3—Cl3 | 2.2 (2) |
O1—N1—C1—C2 | 179.4 (2) | C1—C2—C3—Cl3 | −177.65 (11) |
O2—N1—C1—C2 | 0.58 (17) | C2—C3—C4—C5 | −1.1 (3) |
O1—N1—C1—C6 | −0.3 (4) | Cl3—C3—C4—C5 | 178.10 (13) |
O2—N1—C1—C6 | −179.11 (17) | C3—C4—C5—C6 | −0.2 (3) |
O2—N2—C2—C1 | 0.10 (18) | C4—C5—C6—C1 | 0.9 (3) |
O2—N2—C2—C3 | −179.77 (16) | C4—C5—C6—Cl6 | −178.49 (13) |
N1—C1—C2—N2 | −0.46 (19) | N1—C1—C6—C5 | 179.25 (17) |
C6—C1—C2—N2 | 179.27 (16) | C2—C1—C6—C5 | −0.4 (3) |
N1—C1—C2—C3 | 179.42 (15) | N1—C1—C6—Cl6 | −1.3 (3) |
C6—C1—C2—C3 | −0.8 (2) | C2—C1—C6—Cl6 | 179.01 (12) |
(DCL-II) 4,7-dichlorobenzo[
c]furazan 1-oxide, polymorph II
top
Crystal data top
C6H2Cl2N2O2 | F(000) = 2448 |
Mr = 205.00 | Dx = 1.804 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1162 reflections |
a = 21.828 (5) Å | θ = 2.0–27.4° |
b = 7.819 (2) Å | µ = 0.81 mm−1 |
c = 27.501 (7) Å | T = 173 K |
β = 105.21 (3)° | Prism, yellow |
V = 4529 (2) Å3 | 0.45 × 0.20 × 0.20 mm |
Z = 24 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 5149 independent reflections |
Radiation source: fine-focus sealed tube | 4301 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
ω scans | θmax = 27.5°, θmin = 1.5° |
Absorption correction: multi-scan [SADABS; Sheldrick (1996) and Blessing (1995)] | h = −28→24 |
Tmin = 0.72, Tmax = 0.85 | k = −10→8 |
13985 measured reflections | l = −33→35 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.035P)2 + 4.8P] where P = (Fo2 + 2Fc2)/3 |
5149 reflections | (Δ/σ)max = 0.002 |
325 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1A | 0.61139 (7) | 0.51732 (19) | 0.60152 (6) | 0.0260 (3) | |
O1A | 0.58337 (7) | 0.62123 (17) | 0.56988 (5) | 0.0348 (3) | |
O2A | 0.65613 (6) | 0.58340 (16) | 0.64651 (5) | 0.0315 (3) | |
N2A | 0.68149 (8) | 0.4496 (2) | 0.67789 (6) | 0.0294 (3) | |
C1A | 0.61222 (8) | 0.3477 (2) | 0.60691 (6) | 0.0225 (4) | |
C2A | 0.65534 (8) | 0.3104 (2) | 0.65400 (6) | 0.0231 (4) | |
C3A | 0.66634 (8) | 0.1359 (2) | 0.66930 (7) | 0.0259 (4) | |
C4A | 0.63529 (9) | 0.0132 (2) | 0.63739 (7) | 0.0299 (4) | |
H4A | 0.6424 | −0.1010 | 0.6466 | 0.036* | |
C5A | 0.59196 (9) | 0.0534 (2) | 0.58991 (7) | 0.0290 (4) | |
H5A | 0.5717 | −0.0353 | 0.5694 | 0.035* | |
C6A | 0.57953 (8) | 0.2171 (2) | 0.57395 (7) | 0.0246 (4) | |
Cl3A | 0.71888 (2) | 0.08942 (7) | 0.726290 (17) | 0.03335 (12) | |
Cl6A | 0.52698 (2) | 0.26927 (6) | 0.517471 (16) | 0.03120 (12) | |
N1B | 0.38241 (7) | 0.6371 (2) | 0.22086 (5) | 0.0253 (3) | |
O1B | 0.41019 (7) | 0.74086 (17) | 0.25229 (5) | 0.0330 (3) | |
O2B | 0.33918 (6) | 0.70318 (17) | 0.17476 (5) | 0.0316 (3) | |
N2B | 0.31265 (7) | 0.5682 (2) | 0.14430 (6) | 0.0294 (4) | |
C1B | 0.37978 (8) | 0.4670 (2) | 0.21649 (6) | 0.0222 (4) | |
C2B | 0.33703 (8) | 0.4294 (2) | 0.16923 (7) | 0.0236 (4) | |
C3B | 0.32499 (9) | 0.2550 (2) | 0.15467 (7) | 0.0269 (4) | |
C4B | 0.35485 (9) | 0.1330 (2) | 0.18709 (8) | 0.0317 (4) | |
H4B | 0.3471 | 0.0188 | 0.1782 | 0.038* | |
C5B | 0.39811 (9) | 0.1732 (2) | 0.23476 (7) | 0.0317 (4) | |
H5B | 0.4175 | 0.0846 | 0.2558 | 0.038* | |
C6B | 0.41132 (8) | 0.3367 (2) | 0.24985 (7) | 0.0252 (4) | |
Cl3B | 0.27372 (2) | 0.20943 (7) | 0.096950 (18) | 0.03570 (13) | |
Cl6B | 0.46495 (2) | 0.39035 (7) | 0.305879 (17) | 0.03264 (12) | |
N1C | 0.14069 (8) | −0.0164 (2) | −0.02400 (6) | 0.0290 (3) | |
O1C | 0.17316 (7) | 0.06822 (19) | 0.01082 (5) | 0.0400 (4) | |
O2C | 0.10012 (7) | 0.07642 (17) | −0.06643 (5) | 0.0329 (3) | |
N2C | 0.06714 (8) | −0.0381 (2) | −0.10139 (6) | 0.0296 (3) | |
C1C | 0.13052 (8) | −0.1818 (2) | −0.03501 (6) | 0.0233 (4) | |
C2C | 0.08570 (8) | −0.1913 (2) | −0.08255 (6) | 0.0236 (4) | |
C3C | 0.06615 (8) | −0.3546 (2) | −0.10421 (7) | 0.0251 (4) | |
C4C | 0.09008 (9) | −0.4954 (2) | −0.07769 (7) | 0.0299 (4) | |
H4C | 0.0770 | −0.6026 | −0.0911 | 0.036* | |
C5C | 0.13526 (9) | −0.4846 (3) | −0.02923 (7) | 0.0302 (4) | |
H5C | 0.1505 | −0.5849 | −0.0121 | 0.036* | |
C6C | 0.15622 (8) | −0.3322 (3) | −0.00787 (7) | 0.0262 (4) | |
Cl3C | 0.01400 (2) | −0.35943 (7) | −0.163298 (17) | 0.03510 (12) | |
Cl6C | 0.21209 (2) | −0.31949 (7) | 0.049213 (17) | 0.03537 (13) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1A | 0.0283 (8) | 0.0226 (8) | 0.0255 (8) | 0.0003 (6) | 0.0041 (6) | 0.0003 (6) |
O1A | 0.0397 (8) | 0.0250 (7) | 0.0351 (7) | 0.0051 (6) | 0.0014 (6) | 0.0087 (6) |
O2A | 0.0380 (8) | 0.0218 (7) | 0.0303 (7) | −0.0031 (6) | 0.0013 (6) | −0.0025 (5) |
N2A | 0.0321 (8) | 0.0271 (8) | 0.0260 (8) | −0.0005 (7) | 0.0022 (7) | 0.0008 (6) |
C1A | 0.0234 (8) | 0.0219 (9) | 0.0230 (8) | 0.0019 (7) | 0.0077 (7) | 0.0006 (7) |
C2A | 0.0230 (8) | 0.0255 (9) | 0.0210 (8) | 0.0015 (7) | 0.0059 (7) | −0.0006 (7) |
C3A | 0.0248 (9) | 0.0286 (10) | 0.0243 (9) | 0.0056 (7) | 0.0066 (7) | 0.0050 (7) |
C4A | 0.0361 (10) | 0.0206 (9) | 0.0347 (10) | 0.0045 (8) | 0.0122 (8) | 0.0029 (8) |
C5A | 0.0346 (10) | 0.0230 (10) | 0.0297 (9) | −0.0034 (8) | 0.0091 (8) | −0.0051 (7) |
C6A | 0.0238 (9) | 0.0282 (10) | 0.0216 (8) | −0.0001 (7) | 0.0056 (7) | −0.0021 (7) |
Cl3A | 0.0299 (2) | 0.0420 (3) | 0.0267 (2) | 0.0081 (2) | 0.00500 (18) | 0.01088 (19) |
Cl6A | 0.0284 (2) | 0.0386 (3) | 0.0231 (2) | −0.00095 (19) | 0.00046 (18) | −0.00030 (18) |
N1B | 0.0269 (8) | 0.0241 (8) | 0.0230 (7) | −0.0007 (6) | 0.0032 (6) | −0.0012 (6) |
O1B | 0.0383 (8) | 0.0268 (7) | 0.0301 (7) | −0.0048 (6) | 0.0021 (6) | −0.0080 (6) |
O2B | 0.0379 (8) | 0.0226 (7) | 0.0291 (7) | 0.0011 (6) | −0.0001 (6) | 0.0018 (5) |
N2B | 0.0298 (8) | 0.0291 (9) | 0.0266 (8) | −0.0002 (7) | 0.0023 (7) | −0.0017 (6) |
C1B | 0.0219 (8) | 0.0213 (9) | 0.0241 (8) | −0.0019 (7) | 0.0073 (7) | −0.0019 (7) |
C2B | 0.0227 (9) | 0.0255 (10) | 0.0233 (9) | −0.0003 (7) | 0.0071 (7) | −0.0012 (7) |
C3B | 0.0260 (9) | 0.0286 (10) | 0.0267 (9) | −0.0039 (7) | 0.0081 (7) | −0.0048 (7) |
C4B | 0.0379 (11) | 0.0208 (10) | 0.0379 (11) | −0.0039 (8) | 0.0126 (9) | −0.0041 (8) |
C5B | 0.0374 (10) | 0.0244 (10) | 0.0327 (10) | 0.0041 (8) | 0.0080 (8) | 0.0054 (8) |
C6B | 0.0240 (9) | 0.0278 (10) | 0.0231 (8) | 0.0010 (7) | 0.0054 (7) | 0.0011 (7) |
Cl3B | 0.0314 (2) | 0.0434 (3) | 0.0306 (2) | −0.0075 (2) | 0.00511 (19) | −0.0131 (2) |
Cl6B | 0.0297 (2) | 0.0406 (3) | 0.0241 (2) | 0.00456 (19) | 0.00077 (18) | 0.00018 (19) |
N1C | 0.0307 (8) | 0.0299 (9) | 0.0244 (8) | −0.0022 (7) | 0.0038 (6) | 0.0005 (6) |
O1C | 0.0444 (9) | 0.0380 (8) | 0.0323 (8) | −0.0121 (7) | 0.0007 (6) | −0.0088 (6) |
O2C | 0.0411 (8) | 0.0241 (7) | 0.0301 (7) | 0.0015 (6) | 0.0036 (6) | 0.0017 (5) |
N2C | 0.0329 (8) | 0.0277 (8) | 0.0256 (8) | 0.0014 (7) | 0.0031 (6) | 0.0012 (6) |
C1C | 0.0228 (8) | 0.0246 (9) | 0.0229 (8) | −0.0017 (7) | 0.0067 (7) | −0.0001 (7) |
C2C | 0.0214 (8) | 0.0276 (10) | 0.0222 (8) | 0.0012 (7) | 0.0065 (7) | 0.0038 (7) |
C3C | 0.0233 (8) | 0.0294 (10) | 0.0220 (8) | −0.0017 (7) | 0.0049 (7) | −0.0008 (7) |
C4C | 0.0345 (10) | 0.0238 (10) | 0.0318 (10) | −0.0008 (8) | 0.0095 (8) | −0.0015 (7) |
C5C | 0.0320 (10) | 0.0296 (10) | 0.0293 (10) | 0.0066 (8) | 0.0085 (8) | 0.0069 (8) |
C6C | 0.0218 (8) | 0.0351 (10) | 0.0211 (8) | 0.0033 (7) | 0.0045 (7) | 0.0048 (7) |
Cl3C | 0.0326 (2) | 0.0436 (3) | 0.0245 (2) | −0.0050 (2) | −0.00063 (18) | −0.00347 (19) |
Cl6C | 0.0264 (2) | 0.0520 (3) | 0.0238 (2) | 0.0020 (2) | −0.00040 (18) | 0.0071 (2) |
Geometric parameters (Å, º) top
N1A—O1A | 1.2295 (19) | C3B—C4B | 1.351 (3) |
N1A—C1A | 1.334 (2) | C3B—Cl3B | 1.7225 (19) |
N1A—O2A | 1.455 (2) | C4B—C5B | 1.435 (3) |
O2A—N2A | 1.377 (2) | C4B—H4B | 0.9300 |
N2A—C2A | 1.321 (2) | C5B—C6B | 1.351 (3) |
C1A—C2A | 1.417 (2) | C5B—H5B | 0.9300 |
C1A—C6A | 1.426 (2) | C6B—Cl6B | 1.7246 (19) |
C2A—C3A | 1.430 (3) | N1C—O1C | 1.225 (2) |
C3A—C4A | 1.356 (3) | N1C—C1C | 1.333 (2) |
C3A—Cl3A | 1.7207 (19) | N1C—O2C | 1.460 (2) |
C4A—C5A | 1.432 (3) | O2C—N2C | 1.371 (2) |
C4A—H4A | 0.9300 | N2C—C2C | 1.326 (2) |
C5A—C6A | 1.357 (3) | C1C—C2C | 1.415 (2) |
C5A—H5A | 0.9300 | C1C—C6C | 1.426 (3) |
C6A—Cl6A | 1.7203 (19) | C2C—C3C | 1.426 (3) |
N1B—O1B | 1.2239 (19) | C3C—C4C | 1.348 (3) |
N1B—C1B | 1.335 (2) | C3C—Cl3C | 1.7225 (19) |
N1B—O2B | 1.4618 (19) | C4C—C5C | 1.437 (3) |
O2B—N2B | 1.377 (2) | C4C—H4C | 0.9300 |
N2B—C2B | 1.319 (2) | C5C—C6C | 1.354 (3) |
C1B—C2B | 1.418 (2) | C5C—H5C | 0.9300 |
C1B—C6B | 1.422 (2) | C6C—Cl6C | 1.7196 (19) |
C2B—C3B | 1.426 (3) | | |
| | | |
O1A—N1A—C1A | 136.49 (16) | C4B—C3B—Cl3B | 123.14 (15) |
O1A—N1A—O2A | 117.73 (14) | C2B—C3B—Cl3B | 118.93 (14) |
C1A—N1A—O2A | 105.78 (13) | C3B—C4B—C5B | 122.43 (17) |
N2A—O2A—N1A | 109.45 (12) | C3B—C4B—H4B | 118.8 |
C2A—N2A—O2A | 105.31 (14) | C5B—C4B—H4B | 118.8 |
N1A—C1A—C2A | 106.99 (15) | C6B—C5B—C4B | 121.60 (18) |
N1A—C1A—C6A | 130.62 (17) | C6B—C5B—H5B | 119.2 |
C2A—C1A—C6A | 122.37 (16) | C4B—C5B—H5B | 119.2 |
N2A—C2A—C1A | 112.46 (16) | C5B—C6B—C1B | 116.83 (17) |
N2A—C2A—C3A | 128.51 (16) | C5B—C6B—Cl6B | 123.01 (15) |
C1A—C2A—C3A | 119.02 (16) | C1B—C6B—Cl6B | 120.14 (14) |
C4A—C3A—C2A | 117.92 (16) | O1C—N1C—C1C | 136.81 (17) |
C4A—C3A—Cl3A | 122.73 (15) | O1C—N1C—O2C | 117.47 (15) |
C2A—C3A—Cl3A | 119.34 (14) | C1C—N1C—O2C | 105.72 (14) |
C3A—C4A—C5A | 122.21 (17) | N2C—O2C—N1C | 109.43 (13) |
C3A—C4A—H4A | 118.9 | C2C—N2C—O2C | 105.40 (14) |
C5A—C4A—H4A | 118.9 | N1C—C1C—C2C | 107.13 (16) |
C6A—C5A—C4A | 122.04 (17) | N1C—C1C—C6C | 131.42 (16) |
C6A—C5A—H5A | 119.0 | C2C—C1C—C6C | 121.45 (16) |
C4A—C5A—H5A | 119.0 | N2C—C2C—C1C | 112.32 (16) |
C5A—C6A—C1A | 116.44 (16) | N2C—C2C—C3C | 128.21 (16) |
C5A—C6A—Cl6A | 123.02 (14) | C1C—C2C—C3C | 119.47 (16) |
C1A—C6A—Cl6A | 120.54 (14) | C4C—C3C—C2C | 118.30 (16) |
O1B—N1B—C1B | 136.50 (16) | C4C—C3C—Cl3C | 123.99 (15) |
O1B—N1B—O2B | 117.77 (14) | C2C—C3C—Cl3C | 117.71 (14) |
C1B—N1B—O2B | 105.73 (13) | C3C—C4C—C5C | 121.87 (18) |
N2B—O2B—N1B | 109.24 (13) | C3C—C4C—H4C | 119.1 |
C2B—N2B—O2B | 105.45 (14) | C5C—C4C—H4C | 119.1 |
N1B—C1B—C2B | 106.94 (15) | C6C—C5C—C4C | 121.70 (17) |
N1B—C1B—C6B | 130.81 (16) | C6C—C5C—H5C | 119.2 |
C2B—C1B—C6B | 122.25 (16) | C4C—C5C—H5C | 119.2 |
N2B—C2B—C1B | 112.63 (16) | C5C—C6C—C1C | 117.18 (16) |
N2B—C2B—C3B | 128.41 (17) | C5C—C6C—Cl6C | 121.67 (15) |
C1B—C2B—C3B | 118.95 (16) | C1C—C6C—Cl6C | 121.15 (15) |
C4B—C3B—C2B | 117.93 (17) | | |
(DBR-II) 4,7-dibromobenzo[
c]furazan 1-oxide
top
Crystal data top
C6H2Br2N2O2 | F(000) = 3312 |
Mr = 293.92 | Dx = 2.439 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2707 reflections |
a = 22.810 (6) Å | θ = 2.7–27.2° |
b = 7.835 (2) Å | µ = 10.08 mm−1 |
c = 27.859 (7) Å | T = 175 K |
β = 105.31 (2)° | Prism, yellow |
V = 4802 (2) Å3 | 0.25 × 0.20 × 0.15 mm |
Z = 24 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 5513 independent reflections |
Radiation source: fine-focus sealed tube | 4095 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
ω scans | θmax = 27.5°, θmin = 1.5° |
Absorption correction: multi-scan [SADABS; Sheldrick (1996) and Blessing (1995)] | h = −29→29 |
Tmin = 0.10, Tmax = 0.22 | k = −10→10 |
27206 measured reflections | l = −36→36 |
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.058 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.018P)2 + 6.94P] where P = (Fo2 + 2Fc2)/3 |
5513 reflections | (Δ/σ)max = 0.002 |
325 parameters | Δρmax = 0.92 e Å−3 |
0 restraints | Δρmin = −0.66 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1A | 0.61289 (13) | 0.5134 (4) | 0.60207 (11) | 0.0217 (7) | |
O1A | 0.58574 (12) | 0.6179 (3) | 0.57129 (9) | 0.0293 (6) | |
O2A | 0.65653 (11) | 0.5787 (3) | 0.64577 (9) | 0.0264 (6) | |
N2A | 0.68127 (14) | 0.4436 (4) | 0.67665 (11) | 0.0250 (7) | |
C1A | 0.61297 (15) | 0.3434 (4) | 0.60731 (12) | 0.0167 (7) | |
C2A | 0.65539 (16) | 0.3058 (4) | 0.65353 (12) | 0.0194 (8) | |
C3A | 0.66535 (16) | 0.1311 (5) | 0.66841 (12) | 0.0200 (8) | |
C4A | 0.63449 (16) | 0.0103 (5) | 0.63756 (13) | 0.0248 (8) | |
H4AA | 0.6413 | −0.1061 | 0.6468 | 0.030* | |
C5A | 0.59174 (17) | 0.0510 (5) | 0.59114 (13) | 0.0255 (9) | |
H5AA | 0.5709 | −0.0392 | 0.5709 | 0.031* | |
C6A | 0.58025 (15) | 0.2136 (5) | 0.57533 (12) | 0.0194 (8) | |
Br3A | 0.722237 (17) | 0.07841 (5) | 0.729094 (13) | 0.02587 (9) | |
Br6A | 0.523647 (16) | 0.27066 (5) | 0.515143 (13) | 0.02463 (9) | |
N1B | 0.38075 (13) | 0.6318 (4) | 0.22059 (10) | 0.0208 (7) | |
O1B | 0.40637 (11) | 0.7367 (3) | 0.25162 (9) | 0.0269 (6) | |
O2B | 0.33936 (11) | 0.6971 (3) | 0.17470 (9) | 0.0269 (6) | |
N2B | 0.31437 (13) | 0.5620 (4) | 0.14458 (11) | 0.0226 (7) | |
C1B | 0.37905 (15) | 0.4614 (4) | 0.21596 (12) | 0.0175 (8) | |
C2B | 0.33837 (15) | 0.4240 (4) | 0.16908 (12) | 0.0174 (8) | |
C3B | 0.32676 (16) | 0.2503 (5) | 0.15495 (13) | 0.0222 (8) | |
C4B | 0.35586 (17) | 0.1289 (5) | 0.18693 (14) | 0.0270 (9) | |
H4BA | 0.3485 | 0.0122 | 0.1781 | 0.032* | |
C5B | 0.39738 (17) | 0.1706 (5) | 0.23364 (13) | 0.0248 (8) | |
H5BA | 0.4169 | 0.0805 | 0.2547 | 0.030* | |
C6B | 0.40984 (15) | 0.3328 (5) | 0.24886 (12) | 0.0189 (8) | |
Br3B | 0.271913 (17) | 0.19770 (5) | 0.093357 (13) | 0.02823 (10) | |
Br6B | 0.466884 (17) | 0.38959 (5) | 0.308932 (13) | 0.02531 (10) | |
N1C | 0.14026 (13) | −0.0136 (4) | −0.02499 (10) | 0.0224 (7) | |
O1C | 0.17100 (12) | 0.0710 (3) | 0.00960 (9) | 0.0352 (7) | |
O2C | 0.10200 (11) | 0.0790 (3) | −0.06732 (9) | 0.0270 (6) | |
N2C | 0.07011 (13) | −0.0351 (4) | −0.10183 (10) | 0.0237 (7) | |
C1C | 0.13030 (15) | −0.1792 (5) | −0.03545 (12) | 0.0194 (8) | |
C2C | 0.08732 (15) | −0.1879 (5) | −0.08250 (12) | 0.0175 (7) | |
C3C | 0.06764 (15) | −0.3507 (5) | −0.10343 (12) | 0.0194 (8) | |
C4C | 0.08984 (17) | −0.4906 (5) | −0.07641 (13) | 0.0254 (9) | |
H4CA | 0.0762 | −0.5999 | −0.0894 | 0.031* | |
C5C | 0.13326 (16) | −0.4799 (5) | −0.02887 (13) | 0.0243 (8) | |
H5CA | 0.1476 | −0.5821 | −0.0113 | 0.029* | |
C6C | 0.15429 (15) | −0.3285 (5) | −0.00829 (12) | 0.0212 (8) | |
Br3C | 0.012217 (17) | −0.35598 (5) | −0.166822 (13) | 0.02888 (10) | |
Br6C | 0.214089 (17) | −0.31864 (5) | 0.052689 (13) | 0.02804 (10) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1A | 0.0222 (17) | 0.0171 (17) | 0.0236 (16) | −0.0010 (13) | 0.0024 (13) | 0.0011 (14) |
O1A | 0.0328 (16) | 0.0194 (14) | 0.0308 (14) | 0.0020 (12) | −0.0004 (12) | 0.0071 (12) |
O2A | 0.0330 (16) | 0.0172 (14) | 0.0232 (13) | −0.0029 (11) | −0.0028 (12) | −0.0002 (11) |
N2A | 0.0271 (18) | 0.0204 (18) | 0.0241 (16) | 0.0002 (14) | 0.0006 (14) | 0.0026 (13) |
C1A | 0.0192 (18) | 0.0155 (19) | 0.0162 (17) | −0.0007 (15) | 0.0058 (14) | −0.0018 (14) |
C2A | 0.0210 (19) | 0.016 (2) | 0.0212 (18) | −0.0005 (15) | 0.0055 (15) | −0.0019 (15) |
C3A | 0.0213 (19) | 0.024 (2) | 0.0150 (17) | 0.0043 (15) | 0.0044 (15) | 0.0022 (15) |
C4A | 0.029 (2) | 0.016 (2) | 0.029 (2) | 0.0060 (17) | 0.0072 (17) | 0.0043 (17) |
C5A | 0.029 (2) | 0.020 (2) | 0.026 (2) | −0.0038 (16) | 0.0043 (17) | −0.0044 (16) |
C6A | 0.0196 (19) | 0.023 (2) | 0.0162 (17) | 0.0006 (15) | 0.0046 (15) | −0.0016 (15) |
Br3A | 0.0238 (2) | 0.0306 (2) | 0.02159 (19) | 0.00557 (17) | 0.00312 (15) | 0.00711 (16) |
Br6A | 0.0237 (2) | 0.0274 (2) | 0.01940 (18) | −0.00054 (16) | −0.00028 (15) | 0.00022 (15) |
N1B | 0.0196 (16) | 0.0240 (19) | 0.0167 (15) | 0.0010 (13) | 0.0008 (12) | 0.0025 (13) |
O1B | 0.0318 (16) | 0.0201 (15) | 0.0241 (14) | −0.0032 (12) | −0.0011 (12) | −0.0061 (11) |
O2B | 0.0335 (15) | 0.0162 (14) | 0.0247 (13) | 0.0021 (11) | −0.0035 (11) | 0.0037 (11) |
N2B | 0.0245 (17) | 0.0176 (17) | 0.0218 (16) | −0.0006 (13) | −0.0008 (13) | −0.0016 (13) |
C1B | 0.0198 (19) | 0.0103 (18) | 0.0222 (18) | −0.0032 (14) | 0.0051 (15) | −0.0046 (14) |
C2B | 0.0152 (19) | 0.020 (2) | 0.0186 (17) | 0.0006 (15) | 0.0067 (14) | −0.0004 (14) |
C3B | 0.0195 (19) | 0.023 (2) | 0.024 (2) | −0.0018 (16) | 0.0056 (16) | −0.0031 (16) |
C4B | 0.032 (2) | 0.019 (2) | 0.032 (2) | −0.0043 (17) | 0.0106 (18) | −0.0044 (17) |
C5B | 0.030 (2) | 0.017 (2) | 0.0257 (19) | 0.0021 (17) | 0.0032 (17) | 0.0073 (16) |
C6B | 0.0191 (19) | 0.017 (2) | 0.0195 (17) | −0.0005 (15) | 0.0029 (15) | −0.0024 (15) |
Br3B | 0.0256 (2) | 0.0327 (2) | 0.02414 (19) | −0.00511 (17) | 0.00251 (16) | −0.00977 (17) |
Br6B | 0.0240 (2) | 0.0295 (2) | 0.01888 (17) | 0.00371 (16) | −0.00068 (15) | −0.00004 (16) |
N1C | 0.0242 (17) | 0.0250 (18) | 0.0163 (15) | −0.0030 (14) | 0.0022 (13) | −0.0007 (14) |
O1C | 0.0389 (18) | 0.0309 (17) | 0.0277 (15) | −0.0086 (13) | −0.0055 (13) | −0.0068 (12) |
O2C | 0.0340 (16) | 0.0172 (14) | 0.0246 (14) | 0.0002 (12) | −0.0012 (12) | 0.0022 (11) |
N2C | 0.0278 (18) | 0.0220 (17) | 0.0189 (15) | −0.0012 (14) | 0.0021 (13) | −0.0023 (13) |
C1C | 0.0185 (19) | 0.021 (2) | 0.0174 (17) | 0.0001 (16) | 0.0022 (15) | 0.0012 (15) |
C2C | 0.0163 (18) | 0.018 (2) | 0.0191 (17) | 0.0029 (15) | 0.0067 (14) | 0.0030 (15) |
C3C | 0.0150 (18) | 0.025 (2) | 0.0187 (17) | −0.0020 (15) | 0.0045 (14) | −0.0023 (15) |
C4C | 0.030 (2) | 0.020 (2) | 0.025 (2) | 0.0001 (17) | 0.0053 (16) | 0.0006 (16) |
C5C | 0.027 (2) | 0.024 (2) | 0.0218 (19) | 0.0046 (17) | 0.0061 (16) | 0.0067 (16) |
C6C | 0.0182 (19) | 0.026 (2) | 0.0171 (17) | 0.0023 (16) | 0.0007 (15) | 0.0018 (16) |
Br3C | 0.0280 (2) | 0.0325 (2) | 0.02113 (18) | −0.00316 (17) | −0.00239 (15) | −0.00203 (16) |
Br6C | 0.0216 (2) | 0.0404 (2) | 0.01879 (18) | 0.00137 (18) | −0.00046 (15) | 0.00482 (17) |
Geometric parameters (Å, º) top
N1A—O1A | 1.229 (3) | C3B—C4B | 1.352 (5) |
N1A—C1A | 1.340 (5) | C3B—Br3B | 1.883 (3) |
N1A—O2A | 1.447 (4) | C4B—C5B | 1.430 (5) |
O2A—N2A | 1.387 (4) | C4B—H4BA | 0.9500 |
N2A—C2A | 1.314 (4) | C5B—C6B | 1.346 (5) |
C1A—C2A | 1.422 (5) | C5B—H5BA | 0.9500 |
C1A—C6A | 1.426 (5) | C6B—Br6B | 1.882 (3) |
C2A—C3A | 1.431 (5) | N1C—O1C | 1.226 (4) |
C3A—C4A | 1.345 (5) | N1C—C1C | 1.336 (5) |
C3A—Br3A | 1.885 (3) | N1C—O2C | 1.461 (4) |
C4A—C5A | 1.435 (5) | O2C—N2C | 1.372 (4) |
C4A—H4AA | 0.9500 | N2C—C2C | 1.329 (4) |
C5A—C6A | 1.351 (5) | C1C—C2C | 1.416 (4) |
C5A—H5AA | 0.9500 | C1C—C6C | 1.422 (5) |
C6A—Br6A | 1.880 (3) | C2C—C3C | 1.425 (5) |
N1B—O1B | 1.224 (3) | C3C—C4C | 1.350 (5) |
N1B—C1B | 1.341 (4) | C3C—Br3C | 1.881 (3) |
N1B—O2B | 1.466 (3) | C4C—C5C | 1.431 (5) |
O2B—N2B | 1.378 (4) | C4C—H4CA | 0.9500 |
N2B—C2B | 1.317 (4) | C5C—C6C | 1.349 (5) |
C1B—C6B | 1.417 (5) | C5C—H5CA | 0.9500 |
C1B—C2B | 1.418 (4) | C6C—Br6C | 1.878 (3) |
C2B—C3B | 1.423 (5) | | |
| | | |
O1A—N1A—C1A | 136.5 (3) | C4B—C3B—Br3B | 122.6 (3) |
O1A—N1A—O2A | 117.3 (3) | C2B—C3B—Br3B | 119.5 (3) |
C1A—N1A—O2A | 106.2 (3) | C3B—C4B—C5B | 122.0 (3) |
N2A—O2A—N1A | 109.2 (2) | C3B—C4B—H4BA | 119.0 |
C2A—N2A—O2A | 105.4 (3) | C5B—C4B—H4BA | 119.0 |
N1A—C1A—C2A | 106.6 (3) | C6B—C5B—C4B | 122.4 (3) |
N1A—C1A—C6A | 131.0 (3) | C6B—C5B—H5BA | 118.8 |
C2A—C1A—C6A | 122.4 (3) | C4B—C5B—H5BA | 118.8 |
N2A—C2A—C1A | 112.6 (3) | C5B—C6B—C1B | 116.1 (3) |
N2A—C2A—C3A | 128.8 (3) | C5B—C6B—Br6B | 122.8 (3) |
C1A—C2A—C3A | 118.6 (3) | C1B—C6B—Br6B | 121.0 (3) |
C4A—C3A—C2A | 118.1 (3) | O1C—N1C—C1C | 136.5 (3) |
C4A—C3A—Br3A | 122.6 (3) | O1C—N1C—O2C | 117.5 (3) |
C2A—C3A—Br3A | 119.2 (3) | C1C—N1C—O2C | 106.0 (3) |
C3A—C4A—C5A | 122.4 (3) | N2C—O2C—N1C | 109.6 (2) |
C3A—C4A—H4AA | 118.8 | C2C—N2C—O2C | 104.9 (3) |
C5A—C4A—H4AA | 118.8 | N1C—C1C—C2C | 106.5 (3) |
C6A—C5A—C4A | 122.0 (3) | N1C—C1C—C6C | 131.6 (3) |
C6A—C5A—H5AA | 119.0 | C2C—C1C—C6C | 121.9 (3) |
C4A—C5A—H5AA | 119.0 | N2C—C2C—C1C | 113.0 (3) |
C5A—C6A—C1A | 116.4 (3) | N2C—C2C—C3C | 127.8 (3) |
C5A—C6A—Br6A | 122.9 (3) | C1C—C2C—C3C | 119.2 (3) |
C1A—C6A—Br6A | 120.7 (3) | C4C—C3C—C2C | 117.9 (3) |
O1B—N1B—C1B | 137.1 (3) | C4C—C3C—Br3C | 124.4 (3) |
O1B—N1B—O2B | 117.3 (3) | C2C—C3C—Br3C | 117.7 (3) |
C1B—N1B—O2B | 105.5 (3) | C3C—C4C—C5C | 122.3 (4) |
N2B—O2B—N1B | 109.3 (2) | C3C—C4C—H4CA | 118.9 |
C2B—N2B—O2B | 105.4 (3) | C5C—C4C—H4CA | 118.9 |
N1B—C1B—C6B | 130.4 (3) | C6C—C5C—C4C | 121.8 (3) |
N1B—C1B—C2B | 106.8 (3) | C6C—C5C—H5CA | 119.1 |
C6B—C1B—C2B | 122.8 (3) | C4C—C5C—H5CA | 119.1 |
N2B—C2B—C1B | 112.9 (3) | C5C—C6C—C1C | 116.9 (3) |
N2B—C2B—C3B | 128.3 (3) | C5C—C6C—Br6C | 120.8 (3) |
C1B—C2B—C3B | 118.7 (3) | C1C—C6C—Br6C | 122.2 (3) |
C4B—C3B—C2B | 117.9 (3) | | |
Intermolecular C-H···O-N hydrogen contacts in (I) and (II) (Å, °) topC-H···O-N | C-H | H···O | C···O | C-H···O | H···O-N |
C4-H4···O2i-N2i | 0.95 | 2.49 | 3.336 (2) | 149 | 123 |
C5-H5···O1i-N1i | 0.91 | 2.76 | 3.593 (2) | 154 | 116 |
C4A-H4A···O2Aii-N2Aii | 0.93 | 2.49 | 3.391 (2) | 165 | 107 |
C5A-H5A···O1Aii-N1Aii | 0.93 | 2.70 | 3.421 (2) | 135 | 134 |
C4B-H4B···O2Bii-N2Bii | 0.93 | 2.47 | 3.386 (2) | 167 | 143 |
C5B-H5B···O1Bii-N1Bii | 0.93 | 2.69 | 3.415 (2) | 135 | 135 |
C4C-H4C···O2Cii-N2Cii | 0.93 | 2.61 | 3.364 (2) | 138 | 115 |
C5C-H5C···O1Cii-N1Cii | 0.93 | 2.80 | 3.694 (2) | 162 | 108 |
C4A-H4A···O2Aii-N2Aii | 0.95 | 2.50 | 3.417 (5) | 164 | 107 |
C5A-H5A···O1Aii-N1Aii | 0.95 | 2.71 | 3.435 (5) | 134 | 135 |
C4B-H4B···O2Bii-N2Bii | 0.95 | 2.48 | 3.411 (4) | 168 | 144 |
C5B-H5B···O1Bii-N1Bii | 0.95 | 2.70 | 3.434 (4) | 134 | 136 |
C4C-H4C···O2Cii-N2Cii | 0.95 | 2.62 | 3.387 (5) | 138 | 115 |
C5C-H5C···O1Cii-N1Cii | 0.95 | 2.80 | 3.713 (4) | 161 | 109 |
%T
{σymcodesfn (i) $1+x, 1+y, z$; (ii) $x, y-1, z$.} |
Distances and angles in the C-X···Y-Z contacts in (I) and (II) (Å, °) topC-X···Y-Z | C-X···Y | X···Y | X···Y-Z |
C3-Cl3···O1i-N1i | 157.7 (2) | 3.010 (2) | 166.3 (2) |
C6-Cl6···N2ii-O2ii | 156.3 (2) | 3.191 (2) | 119.3 (2) |
C3A-Cl3A···N2Aiii-O2Aiii | 170.8 (2) | 3.140 (2) | 109.7 (2) |
C6A-Cl6A···O1Aiv-N1Aiv | 168.8 (2) | 3.045 (2) | 152.6 (2) |
C3B-Cl3B···O1C-N1C | 166.4 (2) | 2.987 (2) | 166.8 (2) |
C6B-Cl6B···N2Cv-O2Cv | 171.0 (2) | 3.135 (2) | 117.4 (2) |
C3C-Cl3C···O1Bvi-N1Bvi | 157.0 (2) | 2.936 (2) | 154.7 (2) |
C6C-Cl6C···N2Bvii-O2Bvii | 159.9 (2) | 3.068 (2) | 113.1 (2) |
C3A-Br3A···N2Aiii-O2Aiii | 172.3 (4) | 3.131 (3) | 110.1 (3) |
C6A-Br6A···O1Aiv-N1Aiv | 169.1 (4) | 3.100 (3) | 152.1 (3) |
C3B-Br6B···O1C-N1C | 167.4 (4) | 2.982 (3) | 163.4 (3) |
C6B-Br6B···N2Cv-O2Cv | 169.8 (4) | 3.151 (3) | 117.7 (3) |
C3C-Br3C···O1Bvi-N1Bvi | 155.9 (4) | 2.995 (3) | 152.2 (3) |
C6C-Br6C···N2Bvii-O2Bvii | 159.7 (4) | 3.093 (3) | 111.6 (3) |
%T
{σymcodesfn (i) $1+x,1+y.1+z$; (ii) $x,y,z-1$; (iii) $
{σcriptscriptstyle{3οver 2}}-x,y-{σcriptscriptstyle{1οver 2}},
{σcriptscriptstyle{3οver 2}}-z$; (iv) $1-x,1-y,1-z$; (v)
${σcriptscriptstyle{1οver 2}}+x, {σcriptscriptstyle{1οver 2}}-y,
{σcriptscriptstyle{1οver 2}}+z$;
(vi) $x-{σcriptscriptstyle{1οver 2}}, {σcriptscriptstyle{1οver 2}}-y,
z-{σcriptscriptstyle{1οver 2}}$; (vii) $x,y-1,z$.} |