Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768105038267/de5020sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768105038267/de5020MClsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768105038267/de5020MCl-Bzsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768105038267/de5020MCl-Xysup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768105038267/de5020MBr-Asup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768105038267/de5020MBr-Bsup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768105038267/de5020MI-Asup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768105038267/de5020MI-Csup8.hkl |
CCDC references: 298308; 298309; 298310; 298311; 298312; 298313; 298314
For all compounds, data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C7H3Cl2NO | Z = 4 |
Mr = 188.00 | F(000) = 376 |
Triclinic, P1 | Dx = 1.686 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.3325 (18) Å | Cell parameters from 1913 reflections |
b = 8.999 (2) Å | θ = 2.8–25.9° |
c = 12.221 (3) Å | µ = 0.81 mm−1 |
α = 78.65 (1)° | T = 174 K |
β = 74.39 (1)° | Plate, colorless |
γ = 74.23 (1)° | 0.40 × 0.25 × 0.10 mm |
V = 740.7 (3) Å3 |
Siemens area detector diffractometer | 3362 independent reflections |
Radiation source: fine-focus sealed tube | 2309 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
ω scans | θmax = 27.5°, θmin = 1.8° |
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995' | h = −9→9 |
Tmin = 0.80, Tmax = 0.92 | k = −11→11 |
8796 measured reflections | l = −15→15 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.029P)2 + 0.054P] where P = (Fo2 + 2Fc2)/3 |
3362 reflections | (Δ/σ)max = 0.003 |
199 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C7H3Cl2NO | γ = 74.23 (1)° |
Mr = 188.00 | V = 740.7 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 7.3325 (18) Å | Mo Kα radiation |
b = 8.999 (2) Å | µ = 0.81 mm−1 |
c = 12.221 (3) Å | T = 174 K |
α = 78.65 (1)° | 0.40 × 0.25 × 0.10 mm |
β = 74.39 (1)° |
Siemens area detector diffractometer | 3362 independent reflections |
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995' | 2309 reflections with I > 2σ(I) |
Tmin = 0.80, Tmax = 0.92 | Rint = 0.054 |
8796 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.34 e Å−3 |
3362 reflections | Δρmin = −0.28 e Å−3 |
199 parameters |
x | y | z | Uiso*/Ueq | ||
Cl13 | 0.44792 (10) | 0.47127 (7) | 0.27629 (6) | 0.03104 (18) | |
Cl15 | 0.04364 (11) | 0.56389 (8) | 0.70496 (6) | 0.0365 (2) | |
O14 | 0.2177 (3) | 0.38864 (19) | 0.51401 (15) | 0.0301 (4) | |
H14 | 0.2711 | 0.3403 | 0.4571 | 0.036* | |
N17 | 0.3350 (4) | 1.1216 (3) | 0.4097 (2) | 0.0372 (6) | |
C17 | 0.3216 (4) | 0.9954 (3) | 0.4245 (2) | 0.0287 (6) | |
C11 | 0.2982 (4) | 0.8376 (3) | 0.4456 (2) | 0.0251 (6) | |
C12 | 0.3819 (4) | 0.7403 (3) | 0.3608 (2) | 0.0234 (6) | |
H12 | 0.4580 | 0.7758 | 0.2892 | 0.028* | |
C13 | 0.3519 (4) | 0.5911 (3) | 0.3828 (2) | 0.0219 (6) | |
C14 | 0.2479 (4) | 0.5332 (3) | 0.4884 (2) | 0.0223 (6) | |
C15 | 0.1700 (4) | 0.6329 (3) | 0.5724 (2) | 0.0234 (6) | |
C16 | 0.1923 (4) | 0.7835 (3) | 0.5512 (2) | 0.0265 (6) | |
H16 | 0.1353 | 0.8504 | 0.6087 | 0.032* | |
Cl23 | 0.26550 (10) | 1.08330 (7) | 1.14836 (5) | 0.02751 (17) | |
Cl25 | 0.18386 (10) | 1.09927 (7) | 0.72286 (5) | 0.03108 (18) | |
O24 | 0.2355 (3) | 1.22312 (18) | 0.90769 (15) | 0.0291 (4) | |
H24 | 0.2479 | 1.2578 | 0.9636 | 0.035* | |
N27 | 0.2523 (3) | 0.4597 (3) | 1.0168 (2) | 0.0349 (6) | |
C27 | 0.2504 (4) | 0.5887 (3) | 1.0014 (2) | 0.0267 (6) | |
C21 | 0.2481 (4) | 0.7533 (3) | 0.9794 (2) | 0.0214 (5) | |
C22 | 0.2609 (3) | 0.8279 (3) | 1.0652 (2) | 0.0228 (6) | |
H22 | 0.2730 | 0.7719 | 1.1384 | 0.027* | |
C23 | 0.2557 (3) | 0.9854 (3) | 1.0420 (2) | 0.0209 (5) | |
C24 | 0.2380 (3) | 1.0709 (3) | 0.9358 (2) | 0.0207 (5) | |
C25 | 0.2188 (3) | 0.9925 (3) | 0.8520 (2) | 0.0215 (5) | |
C26 | 0.2255 (3) | 0.8356 (3) | 0.8729 (2) | 0.0229 (6) | |
H26 | 0.2148 | 0.7836 | 0.8152 | 0.027* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl13 | 0.0393 (4) | 0.0233 (3) | 0.0302 (4) | −0.0077 (3) | −0.0021 (3) | −0.0106 (3) |
Cl15 | 0.0483 (5) | 0.0360 (4) | 0.0256 (4) | −0.0190 (3) | 0.0002 (3) | −0.0039 (3) |
O14 | 0.0452 (12) | 0.0186 (9) | 0.0287 (10) | −0.0137 (8) | −0.0055 (9) | −0.0033 (8) |
N17 | 0.0551 (17) | 0.0206 (12) | 0.0396 (15) | −0.0118 (11) | −0.0139 (13) | −0.0041 (11) |
C17 | 0.0371 (16) | 0.0232 (15) | 0.0291 (15) | −0.0088 (12) | −0.0106 (12) | −0.0044 (12) |
C11 | 0.0321 (15) | 0.0183 (13) | 0.0289 (15) | −0.0085 (11) | −0.0117 (12) | −0.0021 (11) |
C12 | 0.0282 (14) | 0.0195 (13) | 0.0243 (14) | −0.0060 (11) | −0.0085 (11) | −0.0028 (11) |
C13 | 0.0251 (14) | 0.0172 (13) | 0.0249 (14) | −0.0033 (11) | −0.0073 (11) | −0.0063 (10) |
C14 | 0.0270 (14) | 0.0158 (12) | 0.0259 (14) | −0.0067 (11) | −0.0086 (11) | −0.0011 (11) |
C15 | 0.0306 (15) | 0.0210 (13) | 0.0185 (13) | −0.0079 (11) | −0.0044 (11) | −0.0015 (10) |
C16 | 0.0339 (16) | 0.0211 (13) | 0.0273 (14) | −0.0055 (12) | −0.0085 (12) | −0.0086 (11) |
Cl23 | 0.0384 (4) | 0.0216 (3) | 0.0270 (3) | −0.0093 (3) | −0.0092 (3) | −0.0079 (3) |
Cl25 | 0.0456 (4) | 0.0270 (4) | 0.0231 (3) | −0.0130 (3) | −0.0093 (3) | −0.0008 (3) |
O24 | 0.0482 (12) | 0.0173 (9) | 0.0265 (10) | −0.0138 (8) | −0.0100 (9) | −0.0029 (8) |
N27 | 0.0494 (16) | 0.0202 (12) | 0.0380 (14) | −0.0111 (11) | −0.0112 (12) | −0.0050 (11) |
C27 | 0.0299 (15) | 0.0233 (14) | 0.0275 (15) | −0.0046 (12) | −0.0073 (12) | −0.0061 (12) |
C21 | 0.0225 (14) | 0.0128 (12) | 0.0284 (14) | −0.0042 (10) | −0.0037 (11) | −0.0041 (10) |
C22 | 0.0265 (14) | 0.0194 (13) | 0.0225 (13) | −0.0055 (11) | −0.0055 (11) | −0.0028 (11) |
C23 | 0.0224 (13) | 0.0186 (13) | 0.0237 (13) | −0.0054 (10) | −0.0039 (11) | −0.0087 (11) |
C24 | 0.0237 (13) | 0.0143 (12) | 0.0248 (14) | −0.0083 (10) | −0.0019 (11) | −0.0034 (10) |
C25 | 0.0217 (13) | 0.0222 (13) | 0.0193 (13) | −0.0064 (11) | −0.0023 (11) | −0.0010 (10) |
C26 | 0.0240 (14) | 0.0224 (14) | 0.0250 (14) | −0.0065 (11) | −0.0049 (11) | −0.0086 (11) |
Cl13—C13 | 1.731 (2) | Cl23—C23 | 1.734 (2) |
Cl15—C15 | 1.726 (3) | Cl25—C25 | 1.722 (2) |
O14—C14 | 1.341 (3) | O24—C24 | 1.341 (3) |
O14—H14 | 0.8400 | O24—H24 | 0.8400 |
N17—C17 | 1.141 (3) | N27—C27 | 1.135 (3) |
C17—C11 | 1.442 (3) | C27—C21 | 1.449 (3) |
C11—C16 | 1.387 (4) | C21—C22 | 1.387 (3) |
C11—C12 | 1.393 (3) | C21—C26 | 1.393 (3) |
C12—C13 | 1.382 (3) | C22—C23 | 1.382 (3) |
C12—H12 | 0.9500 | C22—H22 | 0.9500 |
C13—C14 | 1.394 (3) | C23—C24 | 1.392 (3) |
C14—C15 | 1.397 (3) | C24—C25 | 1.408 (3) |
C15—C16 | 1.375 (3) | C25—C26 | 1.375 (3) |
C16—H16 | 0.9500 | C26—H26 | 0.9500 |
C14—O14—H14 | 109.5 | C24—O24—H24 | 109.5 |
N17—C17—C11 | 178.1 (3) | N27—C27—C21 | 178.9 (3) |
C16—C11—C12 | 120.4 (2) | C22—C21—C26 | 120.9 (2) |
C16—C11—C17 | 119.3 (2) | C22—C21—C27 | 120.0 (2) |
C12—C11—C17 | 120.2 (2) | C26—C21—C27 | 119.0 (2) |
C13—C12—C11 | 118.7 (2) | C23—C22—C21 | 118.6 (2) |
C13—C12—H12 | 120.7 | C23—C22—H22 | 120.7 |
C11—C12—H12 | 120.7 | C21—C22—H22 | 120.7 |
C12—C13—C14 | 122.1 (2) | C22—C23—C24 | 122.2 (2) |
C12—C13—Cl13 | 119.14 (19) | C22—C23—Cl23 | 119.8 (2) |
C14—C13—Cl13 | 118.77 (19) | C24—C23—Cl23 | 118.04 (18) |
O14—C14—C13 | 124.1 (2) | O24—C24—C23 | 124.8 (2) |
O14—C14—C15 | 118.3 (2) | O24—C24—C25 | 117.5 (2) |
C13—C14—C15 | 117.6 (2) | C23—C24—C25 | 117.7 (2) |
C16—C15—C14 | 121.3 (2) | C26—C25—C24 | 121.0 (2) |
C16—C15—Cl15 | 119.87 (19) | C26—C25—Cl25 | 120.85 (19) |
C14—C15—Cl15 | 118.79 (19) | C24—C25—Cl25 | 118.11 (18) |
C15—C16—C11 | 119.8 (2) | C25—C26—C21 | 119.5 (2) |
C15—C16—H16 | 120.1 | C25—C26—H26 | 120.2 |
C11—C16—H16 | 120.1 | C21—C26—H26 | 120.2 |
C7H3Cl2NO·0.5(C6H6) | Z = 2 |
Mr = 227.06 | F(000) = 230 |
Triclinic, P1 | Dx = 1.563 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.420 (2) Å | Cell parameters from 2490 reflections |
b = 8.386 (2) Å | θ = 2.6–27.5° |
c = 8.808 (2) Å | µ = 0.63 mm−1 |
α = 73.82 (1)° | T = 174 K |
β = 66.99 (1)° | Prism, colorless |
γ = 79.04 (1)° | 0.50 × 0.45 × 0.40 mm |
V = 482.4 (2) Å3 |
Siemans area detector diffractometer | 2141 independent reflections |
Radiation source: fine-focus sealed tube | 2086 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
ω scans | θmax = 27.5°, θmin = 2.5° |
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995' | h = −9→9 |
Tmin = 0.74, Tmax = 0.78 | k = −10→10 |
5442 measured reflections | l = −11→11 |
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)] = 0.025 | H-atom parameters constrained |
wR(F2) = 0.075 | w = 1/[σ2(Fo2) + (0.039P)2 + 0.211P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.013 |
2141 reflections | Δρmax = 0.46 e Å−3 |
148 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.022 (4) |
C7H3Cl2NO·0.5(C6H6) | γ = 79.04 (1)° |
Mr = 227.06 | V = 482.4 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.420 (2) Å | Mo Kα radiation |
b = 8.386 (2) Å | µ = 0.63 mm−1 |
c = 8.808 (2) Å | T = 174 K |
α = 73.82 (1)° | 0.50 × 0.45 × 0.40 mm |
β = 66.99 (1)° |
Siemans area detector diffractometer | 2141 independent reflections |
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995' | 2086 reflections with I > 2σ(I) |
Tmin = 0.74, Tmax = 0.78 | Rint = 0.015 |
5442 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 0 restraints |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.46 e Å−3 |
2141 reflections | Δρmin = −0.18 e Å−3 |
148 parameters |
x | y | z | Uiso*/Ueq | ||
Cl3 | 0.77557 (5) | 0.61464 (4) | 0.47223 (4) | 0.02601 (11) | |
Cl5 | 0.63236 (6) | −0.03101 (4) | 0.67049 (5) | 0.03356 (12) | |
O4 | 0.83045 (15) | 0.25566 (13) | 0.44919 (12) | 0.0298 (2) | |
H4 | 0.8866 | 0.3412 | 0.3865 | 0.036* | |
N7 | 0.11355 (19) | 0.41555 (16) | 1.15910 (16) | 0.0313 (3) | |
C7 | 0.2352 (2) | 0.38929 (17) | 1.03757 (17) | 0.0246 (3) | |
C1 | 0.38998 (19) | 0.35638 (17) | 0.88546 (16) | 0.0225 (3) | |
C2 | 0.49726 (19) | 0.48661 (17) | 0.76795 (16) | 0.0228 (3) | |
H2 | 0.4692 | 0.5958 | 0.7882 | 0.027* | |
C3 | 0.64521 (19) | 0.45385 (16) | 0.62150 (16) | 0.0208 (3) | |
C4 | 0.69016 (18) | 0.29445 (16) | 0.58880 (16) | 0.0217 (3) | |
C5 | 0.57927 (19) | 0.16651 (16) | 0.70987 (17) | 0.0224 (3) | |
C6 | 0.43020 (19) | 0.19575 (17) | 0.85661 (16) | 0.0230 (3) | |
H6 | 0.3563 | 0.1079 | 0.9366 | 0.028* | |
C11 | 1.0772 (2) | 0.85307 (19) | 0.0809 (2) | 0.0331 (3) | |
H11 | 1.1304 | 0.7521 | 0.1360 | 0.040* | |
C12 | 0.9788 (2) | 0.9766 (2) | 0.16852 (19) | 0.0330 (3) | |
H12 | 0.9643 | 0.9607 | 0.2837 | 0.040* | |
C13 | 0.9019 (2) | 1.12330 (19) | 0.0873 (2) | 0.0325 (3) | |
H13 | 0.8343 | 1.2083 | 0.1469 | 0.039* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl3 | 0.02473 (18) | 0.02516 (18) | 0.02235 (18) | −0.00724 (12) | −0.00319 (13) | −0.00083 (12) |
Cl5 | 0.0370 (2) | 0.02394 (19) | 0.0332 (2) | −0.00511 (14) | −0.00152 (15) | −0.01104 (14) |
O4 | 0.0291 (5) | 0.0301 (5) | 0.0217 (5) | −0.0070 (4) | 0.0044 (4) | −0.0096 (4) |
N7 | 0.0312 (6) | 0.0322 (7) | 0.0242 (6) | −0.0070 (5) | 0.0004 (5) | −0.0094 (5) |
C7 | 0.0252 (7) | 0.0249 (7) | 0.0226 (6) | −0.0055 (5) | −0.0059 (5) | −0.0056 (5) |
C1 | 0.0197 (6) | 0.0285 (7) | 0.0170 (6) | −0.0029 (5) | −0.0035 (5) | −0.0058 (5) |
C2 | 0.0214 (6) | 0.0247 (6) | 0.0213 (6) | −0.0022 (5) | −0.0055 (5) | −0.0067 (5) |
C3 | 0.0197 (6) | 0.0228 (6) | 0.0180 (6) | −0.0051 (5) | −0.0053 (5) | −0.0015 (5) |
C4 | 0.0185 (6) | 0.0271 (7) | 0.0176 (6) | −0.0020 (5) | −0.0038 (5) | −0.0062 (5) |
C5 | 0.0228 (6) | 0.0219 (6) | 0.0219 (6) | −0.0020 (5) | −0.0066 (5) | −0.0059 (5) |
C6 | 0.0217 (6) | 0.0257 (6) | 0.0193 (6) | −0.0051 (5) | −0.0052 (5) | −0.0028 (5) |
C11 | 0.0328 (7) | 0.0262 (7) | 0.0419 (8) | −0.0060 (6) | −0.0169 (7) | −0.0031 (6) |
C12 | 0.0324 (8) | 0.0419 (9) | 0.0257 (7) | −0.0133 (6) | −0.0076 (6) | −0.0068 (6) |
C13 | 0.0267 (7) | 0.0331 (8) | 0.0400 (8) | −0.0043 (6) | −0.0069 (6) | −0.0181 (6) |
Cl3—C3 | 1.7309 (13) | C4—C5 | 1.4062 (18) |
Cl5—C5 | 1.7276 (14) | C5—C6 | 1.3820 (18) |
O4—C4 | 1.3398 (15) | C6—H6 | 0.9500 |
O4—H4 | 0.8400 | C11—C12 | 1.386 (2) |
N7—C7 | 1.1442 (19) | C11—C13i | 1.388 (2) |
C7—C1 | 1.4399 (18) | C11—H11 | 0.9500 |
C1—C6 | 1.3953 (19) | C12—C13 | 1.383 (2) |
C1—C2 | 1.3979 (19) | C12—H12 | 0.9500 |
C2—C3 | 1.3858 (18) | C13—C11i | 1.388 (2) |
C2—H2 | 0.9500 | C13—H13 | 0.9500 |
C3—C4 | 1.3967 (19) | ||
C4—O4—H4 | 109.5 | C6—C5—Cl5 | 120.03 (10) |
N7—C7—C1 | 179.29 (15) | C4—C5—Cl5 | 118.23 (10) |
C6—C1—C2 | 120.88 (12) | C5—C6—C1 | 118.95 (12) |
C6—C1—C7 | 119.76 (12) | C5—C6—H6 | 120.5 |
C2—C1—C7 | 119.36 (12) | C1—C6—H6 | 120.5 |
C3—C2—C1 | 118.91 (12) | C12—C11—C13i | 120.08 (15) |
C3—C2—H2 | 120.5 | C12—C11—H11 | 120.0 |
C1—C2—H2 | 120.5 | C13i—C11—H11 | 120.0 |
C2—C3—C4 | 121.78 (12) | C11—C12—C13 | 119.56 (15) |
C2—C3—Cl3 | 119.53 (10) | C11—C12—H12 | 120.2 |
C4—C3—Cl3 | 118.68 (10) | C13—C12—H12 | 120.2 |
O4—C4—C3 | 124.41 (12) | C12—C13—C11i | 120.36 (14) |
O4—C4—C5 | 117.84 (12) | C12—C13—H13 | 119.8 |
C3—C4—C5 | 117.74 (11) | C11i—C13—H13 | 119.8 |
C6—C5—C4 | 121.74 (12) |
Symmetry code: (i) −x+2, −y+2, −z. |
C7H3Cl2NO·0.25(C8H10) | F(000) = 434 |
Mr = 214.55 | Dx = 1.539 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3547 reflections |
a = 4.5522 (11) Å | θ = 2.7–27.2° |
b = 15.067 (4) Å | µ = 0.65 mm−1 |
c = 13.636 (3) Å | T = 174 K |
β = 98.00 (1)° | Needle, colorless |
V = 926.2 (4) Å3 | 0.40 × 0.15 × 0.10 mm |
Z = 4 |
Siemens area detector diffractometer | 1636 independent reflections |
Radiation source: fine-focus sealed tube | 1317 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995' | h = −5→5 |
Tmin = 0.88, Tmax = 0.94 | k = −17→17 |
8934 measured reflections | l = −16→16 |
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)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.079 | w = 1/[σ2(Fo2) + (0.022P)2 + 0.43P] where P = (Fo2 + 2Fc2)/3 |
S = 1.22 | (Δ/σ)max = 0.023 |
1636 reflections | Δρmax = 0.22 e Å−3 |
151 parameters | Δρmin = −0.19 e Å−3 |
67 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0043 (16) |
C7H3Cl2NO·0.25(C8H10) | V = 926.2 (4) Å3 |
Mr = 214.55 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 4.5522 (11) Å | µ = 0.65 mm−1 |
b = 15.067 (4) Å | T = 174 K |
c = 13.636 (3) Å | 0.40 × 0.15 × 0.10 mm |
β = 98.00 (1)° |
Siemens area detector diffractometer | 1636 independent reflections |
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995' | 1317 reflections with I > 2σ(I) |
Tmin = 0.88, Tmax = 0.94 | Rint = 0.054 |
8934 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 67 restraints |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 1.22 | Δρmax = 0.22 e Å−3 |
1636 reflections | Δρmin = −0.19 e Å−3 |
151 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
04 | 1.2136 (4) | 0.84495 (12) | 0.74697 (13) | 0.0351 (5) | |
H4 | 1.2799 | 0.8003 | 0.7797 | 0.042* | |
C4 | 0.9847 (5) | 0.82074 (17) | 0.67956 (18) | 0.0249 (6) | |
Cl3 | 1.04842 (16) | 0.65090 (4) | 0.74032 (5) | 0.0376 (2) | |
C3 | 0.8767 (5) | 0.73432 (17) | 0.66611 (18) | 0.0245 (6) | |
C2 | 0.6421 (6) | 0.71394 (17) | 0.59419 (18) | 0.0276 (6) | |
H2 | 0.5706 | 0.6548 | 0.5865 | 0.033* | |
C1 | 0.5117 (5) | 0.78098 (17) | 0.53313 (18) | 0.0257 (6) | |
N7 | 0.0819 (5) | 0.74320 (16) | 0.39527 (18) | 0.0423 (6) | |
C6 | 0.6128 (6) | 0.86740 (17) | 0.54498 (19) | 0.0277 (6) | |
H6 | 0.5228 | 0.9131 | 0.5031 | 0.033* | |
Cl5 | 0.96867 (17) | 0.99512 (5) | 0.63438 (6) | 0.0432 (3) | |
C5 | 0.8453 (6) | 0.88677 (17) | 0.61796 (18) | 0.0260 (6) | |
C7 | 0.2710 (6) | 0.76007 (18) | 0.4564 (2) | 0.0307 (7) | |
C11 | 0.176 (3) | 0.508 (2) | 0.4806 (19) | 0.0328 (17) | 0.25 |
C12 | 0.357 (3) | 0.528 (2) | 0.4094 (19) | 0.0324 (16) | 0.25 |
H12A | 0.2690 | 0.5491 | 0.3462 | 0.039* | 0.25 |
C13 | 0.663 (3) | 0.520 (2) | 0.4292 (19) | 0.0325 (17) | 0.25 |
H13A | 0.7814 | 0.5346 | 0.3794 | 0.039* | 0.25 |
C14 | 0.800 (3) | 0.490 (2) | 0.5209 (19) | 0.0328 (17) | 0.25 |
C15 | 0.619 (3) | 0.469 (2) | 0.5921 (19) | 0.0324 (16) | 0.25 |
H15A | 0.7072 | 0.4477 | 0.6551 | 0.039* | 0.25 |
C16 | 0.313 (3) | 0.478 (2) | 0.5724 (19) | 0.0325 (17) | 0.25 |
H16A | 0.1950 | 0.4634 | 0.6224 | 0.039* | 0.25 |
C17 | −0.156 (4) | 0.517 (3) | 0.460 (6) | 0.046 (3) | 0.25 |
H17A | −0.2069 | 0.5760 | 0.4338 | 0.069* | 0.25 |
H17B | −0.2404 | 0.5077 | 0.5215 | 0.069* | 0.25 |
H17C | −0.2354 | 0.4719 | 0.4112 | 0.069* | 0.25 |
C18 | 1.132 (4) | 0.480 (3) | 0.543 (6) | 0.046 (3) | 0.25 |
H18A | 1.2013 | 0.5051 | 0.6081 | 0.069* | 0.25 |
H18B | 1.2237 | 0.5126 | 0.4923 | 0.069* | 0.25 |
H18C | 1.1858 | 0.4175 | 0.5412 | 0.069* | 0.25 |
U11 | U22 | U33 | U12 | U13 | U23 | |
04 | 0.0359 (11) | 0.0308 (11) | 0.0326 (11) | 0.0019 (9) | −0.0170 (9) | −0.0008 (9) |
C4 | 0.0239 (15) | 0.0279 (15) | 0.0213 (14) | 0.0023 (11) | −0.0028 (12) | −0.0033 (11) |
Cl3 | 0.0454 (5) | 0.0297 (4) | 0.0346 (4) | 0.0070 (3) | −0.0050 (3) | 0.0058 (3) |
C3 | 0.0244 (15) | 0.0267 (15) | 0.0220 (14) | 0.0050 (12) | 0.0017 (12) | 0.0025 (11) |
C2 | 0.0278 (15) | 0.0260 (15) | 0.0288 (15) | −0.0025 (12) | 0.0035 (12) | −0.0067 (12) |
C1 | 0.0204 (14) | 0.0328 (16) | 0.0229 (14) | −0.0006 (12) | −0.0011 (11) | −0.0039 (12) |
N7 | 0.0375 (15) | 0.0475 (16) | 0.0375 (14) | −0.0058 (12) | −0.0097 (13) | −0.0027 (12) |
C6 | 0.0263 (15) | 0.0290 (15) | 0.0263 (15) | 0.0038 (12) | −0.0016 (12) | 0.0031 (12) |
Cl5 | 0.0510 (5) | 0.0253 (4) | 0.0469 (5) | −0.0051 (4) | −0.0162 (4) | −0.0002 (3) |
C5 | 0.0271 (15) | 0.0244 (14) | 0.0251 (15) | −0.0012 (11) | −0.0010 (12) | −0.0012 (11) |
C7 | 0.0302 (17) | 0.0318 (16) | 0.0290 (15) | −0.0010 (13) | 0.0003 (14) | −0.0007 (13) |
C11 | 0.038 (4) | 0.021 (3) | 0.041 (4) | 0.001 (3) | 0.009 (3) | −0.003 (3) |
C12 | 0.043 (4) | 0.027 (3) | 0.027 (3) | −0.001 (3) | 0.005 (3) | 0.001 (2) |
C13 | 0.048 (5) | 0.022 (3) | 0.031 (4) | −0.003 (4) | 0.017 (3) | −0.003 (3) |
C14 | 0.038 (4) | 0.021 (3) | 0.041 (4) | 0.001 (3) | 0.009 (3) | −0.003 (3) |
C15 | 0.043 (4) | 0.027 (3) | 0.027 (3) | −0.001 (3) | 0.005 (3) | 0.001 (2) |
C16 | 0.048 (5) | 0.022 (3) | 0.031 (4) | −0.003 (4) | 0.017 (3) | −0.003 (3) |
C17 | 0.043 (5) | 0.044 (5) | 0.051 (5) | 0.001 (5) | 0.006 (6) | −0.007 (5) |
C18 | 0.043 (5) | 0.044 (5) | 0.051 (5) | 0.001 (5) | 0.006 (6) | −0.007 (5) |
04—C4 | 1.341 (3) | C11—C17 | 1.5032 (11) |
04—H4 | 0.8400 | C12—C13 | 1.3899 (10) |
C4—C3 | 1.395 (4) | C12—H12A | 0.9500 |
C4—C5 | 1.396 (3) | C13—C14 | 1.3930 (10) |
Cl3—C3 | 1.730 (2) | C13—H13A | 0.9500 |
C3—C2 | 1.380 (3) | C14—C15 | 1.3929 (10) |
C2—C1 | 1.388 (3) | C14—C18 | 1.5032 (12) |
C2—H2 | 0.9500 | C15—C16 | 1.3899 (10) |
C1—C6 | 1.383 (4) | C15—H15A | 0.9500 |
C1—C7 | 1.441 (4) | C16—H16A | 0.9500 |
N7—C7 | 1.140 (3) | C17—H17A | 0.9800 |
C6—C5 | 1.379 (3) | C17—H17B | 0.9800 |
C6—H6 | 0.9500 | C17—H17C | 0.9800 |
Cl5—C5 | 1.731 (3) | C18—H18A | 0.9800 |
C11—C12 | 1.3929 (10) | C18—H18B | 0.9800 |
C11—C16 | 1.3930 (10) | C18—H18C | 0.9800 |
C4—04—H4 | 109.5 | N7—C7—C1 | 179.5 (3) |
04—C4—C3 | 124.8 (2) | C12—C11—C16 | 117.77 (13) |
04—C4—C5 | 117.6 (2) | C12—C11—C17 | 122 (4) |
C3—C4—C5 | 117.6 (2) | C16—C11—C17 | 121 (4) |
C2—C3—C4 | 121.6 (2) | C13—C12—C11 | 121.12 (13) |
C2—C3—Cl3 | 119.7 (2) | C13—C12—H12A | 119.4 |
C4—C3—Cl3 | 118.61 (19) | C11—C12—H12A | 119.4 |
C3—C2—C1 | 119.2 (2) | C12—C13—C14 | 121.10 (13) |
C3—C2—H2 | 120.4 | C12—C13—H13A | 119.4 |
C1—C2—H2 | 120.4 | C14—C13—H13A | 119.4 |
C6—C1—C2 | 120.5 (2) | C15—C14—C13 | 117.77 (13) |
C6—C1—C7 | 119.9 (2) | C15—C14—C18 | 121 (4) |
C2—C1—C7 | 119.7 (2) | C13—C14—C18 | 121 (4) |
C5—C6—C1 | 119.5 (2) | C16—C15—C14 | 121.12 (13) |
C5—C6—H6 | 120.2 | C16—C15—H15A | 119.4 |
C1—C6—H6 | 120.2 | C14—C15—H15A | 119.4 |
C6—C5—C4 | 121.5 (2) | C15—C16—C11 | 121.10 (13) |
C6—C5—Cl5 | 119.7 (2) | C15—C16—H16A | 119.5 |
C4—C5—Cl5 | 118.82 (19) | C11—C16—H16A | 119.5 |
C7H3Br2NO | Z = 4 |
Mr = 276.92 | F(000) = 520 |
Triclinic, P1 | Dx = 2.348 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.244 (2) Å | Cell parameters from 2861 reflections |
b = 9.120 (2) Å | θ = 2.4–27.5° |
c = 11.687 (3) Å | µ = 10.28 mm−1 |
α = 95.60 (1)° | T = 174 K |
β = 108.55 (1)° | Prism, colorless |
γ = 106.13 (1)° | 0.20 × 0.15 × 0.15 mm |
V = 783.4 (3) Å3 |
Siemens area detector diffractometer | 3568 independent reflections |
Radiation source: fine-focus sealed tube | 3107 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω scans | θmax = 27.5°, θmin = 1.9° |
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995' | h = −10→10 |
Tmin = 0.174, Tmax = 0.214 | k = −11→11 |
9376 measured reflections | l = −15→15 |
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 | H-atom parameters constrained |
wR(F2) = 0.079 | w = 1/[σ2(Fo2) + (0.028P)2 + 2.2P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.006 |
3568 reflections | Δρmax = 0.65 e Å−3 |
200 parameters | Δρmin = −0.61 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0029 (3) |
C7H3Br2NO | γ = 106.13 (1)° |
Mr = 276.92 | V = 783.4 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.244 (2) Å | Mo Kα radiation |
b = 9.120 (2) Å | µ = 10.28 mm−1 |
c = 11.687 (3) Å | T = 174 K |
α = 95.60 (1)° | 0.20 × 0.15 × 0.15 mm |
β = 108.55 (1)° |
Siemens area detector diffractometer | 3568 independent reflections |
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995' | 3107 reflections with I > 2σ(I) |
Tmin = 0.174, Tmax = 0.214 | Rint = 0.027 |
9376 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.65 e Å−3 |
3568 reflections | Δρmin = −0.61 e Å−3 |
200 parameters |
x | y | z | Uiso*/Ueq | ||
C11 | 0.3313 (5) | 0.5626 (5) | 0.7730 (4) | 0.0191 (8) | |
C12 | 0.2655 (6) | 0.6579 (5) | 0.6969 (4) | 0.0203 (8) | |
H12 | 0.2423 | 0.7459 | 0.7300 | 0.024* | |
Br13 | 0.15142 (6) | 0.75285 (5) | 0.46807 (4) | 0.02491 (12) | |
C13 | 0.2350 (6) | 0.6227 (5) | 0.5733 (4) | 0.0214 (8) | |
C14 | 0.2638 (6) | 0.4918 (5) | 0.5218 (4) | 0.0202 (8) | |
O14 | 0.2313 (4) | 0.4505 (4) | 0.4000 (3) | 0.0280 (7) | |
H14 | 0.1922 | 0.5149 | 0.3626 | 0.034* | |
Br15 | 0.36496 (6) | 0.21886 (5) | 0.53131 (4) | 0.02649 (13) | |
C15 | 0.3292 (5) | 0.3990 (4) | 0.5995 (4) | 0.0184 (8) | |
C16 | 0.3655 (5) | 0.4331 (5) | 0.7244 (4) | 0.0196 (8) | |
H16 | 0.4130 | 0.3697 | 0.7766 | 0.023* | |
N17 | 0.4017 (5) | 0.6404 (4) | 1.0065 (3) | 0.0275 (8) | |
C17 | 0.3704 (6) | 0.6033 (5) | 0.9032 (4) | 0.0219 (9) | |
C21 | 0.1629 (5) | 0.2828 (5) | 0.0757 (4) | 0.0191 (8) | |
C22 | 0.2438 (5) | 0.2029 (5) | 0.1612 (4) | 0.0194 (8) | |
H22 | 0.2725 | 0.2367 | 0.2469 | 0.023* | |
Br23 | 0.38345 (6) | −0.03975 (5) | 0.23138 (4) | 0.02698 (13) | |
C23 | 0.2809 (5) | 0.0742 (5) | 0.1186 (4) | 0.0201 (8) | |
O24 | 0.2752 (4) | −0.1024 (3) | −0.0518 (3) | 0.0265 (7) | |
H24 | 0.3238 | −0.1414 | 0.0066 | 0.040* | |
C24 | 0.2412 (6) | 0.0233 (4) | −0.0067 (4) | 0.0205 (8) | |
Br25 | 0.10256 (6) | 0.03445 (5) | −0.25968 (4) | 0.02639 (13) | |
C25 | 0.1602 (5) | 0.1054 (4) | −0.0892 (3) | 0.0175 (8) | |
C26 | 0.1214 (5) | 0.2337 (5) | −0.0497 (4) | 0.0192 (8) | |
H26 | 0.0669 | 0.2884 | −0.1074 | 0.023* | |
C27 | 0.1232 (6) | 0.4164 (5) | 0.1214 (4) | 0.0242 (9) | |
N27 | 0.0903 (6) | 0.5194 (5) | 0.1612 (3) | 0.0331 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.0168 (19) | 0.0197 (19) | 0.0177 (18) | 0.0034 (16) | 0.0049 (15) | 0.0023 (15) |
C12 | 0.022 (2) | 0.0173 (19) | 0.023 (2) | 0.0074 (16) | 0.0083 (17) | 0.0039 (15) |
Br13 | 0.0301 (3) | 0.0252 (2) | 0.0237 (2) | 0.01436 (19) | 0.00877 (18) | 0.01145 (16) |
C13 | 0.024 (2) | 0.0183 (19) | 0.022 (2) | 0.0083 (17) | 0.0070 (17) | 0.0075 (16) |
C14 | 0.022 (2) | 0.021 (2) | 0.0169 (18) | 0.0061 (17) | 0.0068 (16) | 0.0027 (15) |
O14 | 0.043 (2) | 0.0292 (16) | 0.0175 (14) | 0.0196 (15) | 0.0109 (14) | 0.0078 (12) |
Br15 | 0.0380 (3) | 0.0234 (2) | 0.0232 (2) | 0.01689 (19) | 0.01198 (19) | 0.00432 (16) |
C15 | 0.019 (2) | 0.0151 (18) | 0.0216 (19) | 0.0064 (16) | 0.0076 (16) | 0.0011 (15) |
C16 | 0.018 (2) | 0.0182 (19) | 0.0213 (19) | 0.0055 (16) | 0.0055 (16) | 0.0049 (15) |
N17 | 0.039 (2) | 0.0266 (19) | 0.0198 (18) | 0.0158 (17) | 0.0096 (16) | 0.0042 (15) |
C17 | 0.022 (2) | 0.0162 (19) | 0.026 (2) | 0.0086 (16) | 0.0058 (17) | 0.0036 (16) |
C21 | 0.017 (2) | 0.0172 (19) | 0.023 (2) | 0.0051 (16) | 0.0086 (16) | 0.0043 (16) |
C22 | 0.018 (2) | 0.0182 (19) | 0.0197 (19) | 0.0036 (16) | 0.0065 (16) | 0.0036 (15) |
Br23 | 0.0349 (3) | 0.0253 (2) | 0.0239 (2) | 0.01680 (19) | 0.00730 (18) | 0.01010 (17) |
C23 | 0.018 (2) | 0.0189 (19) | 0.024 (2) | 0.0062 (16) | 0.0074 (16) | 0.0092 (16) |
O24 | 0.0357 (18) | 0.0250 (15) | 0.0245 (15) | 0.0199 (14) | 0.0098 (14) | 0.0056 (12) |
C24 | 0.021 (2) | 0.0153 (18) | 0.025 (2) | 0.0055 (16) | 0.0098 (17) | 0.0032 (16) |
Br25 | 0.0372 (3) | 0.0276 (2) | 0.0184 (2) | 0.0156 (2) | 0.01084 (18) | 0.00519 (16) |
C25 | 0.017 (2) | 0.0186 (19) | 0.0158 (18) | 0.0034 (16) | 0.0066 (15) | 0.0036 (15) |
C26 | 0.0155 (19) | 0.0209 (19) | 0.0222 (19) | 0.0071 (16) | 0.0068 (16) | 0.0055 (16) |
C27 | 0.031 (2) | 0.026 (2) | 0.0169 (19) | 0.0116 (19) | 0.0071 (17) | 0.0086 (16) |
N27 | 0.052 (3) | 0.033 (2) | 0.0218 (18) | 0.028 (2) | 0.0115 (18) | 0.0052 (16) |
C11—C12 | 1.396 (5) | C21—C26 | 1.391 (5) |
C11—C16 | 1.397 (5) | C21—C22 | 1.401 (5) |
C11—C17 | 1.438 (6) | C21—C27 | 1.443 (5) |
C12—C13 | 1.373 (6) | C22—C23 | 1.379 (6) |
C12—H12 | 0.9500 | C22—H22 | 0.9500 |
Br13—C13 | 1.896 (4) | Br23—C23 | 1.892 (4) |
C13—C14 | 1.398 (5) | C23—C24 | 1.395 (6) |
C14—O14 | 1.356 (5) | O24—C24 | 1.351 (5) |
C14—C15 | 1.386 (5) | O24—H24 | 0.8400 |
O14—H14 | 0.8400 | C24—C25 | 1.395 (5) |
Br15—C15 | 1.893 (4) | Br25—C25 | 1.894 (4) |
C15—C16 | 1.378 (5) | C25—C26 | 1.372 (5) |
C16—H16 | 0.9500 | C26—H26 | 0.9500 |
N17—C17 | 1.145 (5) | C27—N27 | 1.144 (5) |
C12—C11—C16 | 120.6 (4) | C26—C21—C22 | 120.7 (4) |
C12—C11—C17 | 118.9 (4) | C26—C21—C27 | 121.2 (4) |
C16—C11—C17 | 120.4 (4) | C22—C21—C27 | 118.1 (4) |
C13—C12—C11 | 119.0 (4) | C23—C22—C21 | 118.7 (4) |
C13—C12—H12 | 120.5 | C23—C22—H22 | 120.6 |
C11—C12—H12 | 120.5 | C21—C22—H22 | 120.6 |
C12—C13—C14 | 121.6 (4) | C22—C23—C24 | 121.6 (4) |
C12—C13—Br13 | 120.1 (3) | C22—C23—Br23 | 119.7 (3) |
C14—C13—Br13 | 118.4 (3) | C24—C23—Br23 | 118.7 (3) |
O14—C14—C15 | 118.2 (3) | C24—O24—H24 | 109.5 |
O14—C14—C13 | 123.6 (4) | O24—C24—C23 | 123.2 (4) |
C15—C14—C13 | 118.3 (4) | O24—C24—C25 | 118.6 (3) |
C14—O14—H14 | 109.5 | C23—C24—C25 | 118.1 (3) |
C16—C15—C14 | 121.7 (3) | C26—C25—C24 | 121.7 (4) |
C16—C15—Br15 | 119.3 (3) | C26—C25—Br25 | 120.1 (3) |
C14—C15—Br15 | 119.0 (3) | C24—C25—Br25 | 118.2 (3) |
C15—C16—C11 | 118.9 (4) | C25—C26—C21 | 119.2 (4) |
C15—C16—H16 | 120.6 | C25—C26—H26 | 120.4 |
C11—C16—H16 | 120.6 | C21—C26—H26 | 120.4 |
N17—C17—C11 | 177.8 (4) | N27—C27—C21 | 177.3 (5) |
C7H3Br2NO | Z = 4 |
Mr = 276.92 | F(000) = 520 |
Triclinic, P1 | Dx = 2.344 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 3.9684 (10) Å | Cell parameters from 2619 reflections |
b = 12.669 (3) Å | θ = 2.8–27.2° |
c = 16.047 (4) Å | µ = 10.26 mm−1 |
α = 79.68 (1)° | T = 174 K |
β = 83.71 (1)° | Plate, colorless |
γ = 83.06 (1)° | 0.40 × 0.20 × 0.08 mm |
V = 784.7 (3) Å3 |
Siemens area detector diffractometer | 3510 independent reflections |
Radiation source: fine-focus sealed tube | 2975 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
ω scans | θmax = 27.5°, θmin = 1.3° |
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995' | h = −5→5 |
Tmin = 0.105, Tmax = 0.440 | k = −16→16 |
8883 measured reflections | l = −20→20 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.066P)2 + 0.42P] where P = (Fo2 + 2Fc2)/3 |
3510 reflections | (Δ/σ)max = 0.002 |
200 parameters | Δρmax = 1.74 e Å−3 |
0 restraints | Δρmin = −1.61 e Å−3 |
C7H3Br2NO | γ = 83.06 (1)° |
Mr = 276.92 | V = 784.7 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 3.9684 (10) Å | Mo Kα radiation |
b = 12.669 (3) Å | µ = 10.26 mm−1 |
c = 16.047 (4) Å | T = 174 K |
α = 79.68 (1)° | 0.40 × 0.20 × 0.08 mm |
β = 83.71 (1)° |
Siemens area detector diffractometer | 3510 independent reflections |
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995' | 2975 reflections with I > 2σ(I) |
Tmin = 0.105, Tmax = 0.440 | Rint = 0.042 |
8883 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.09 | Δρmax = 1.74 e Å−3 |
3510 reflections | Δρmin = −1.61 e Å−3 |
200 parameters |
x | y | z | Uiso*/Ueq | ||
C11 | −0.0095 (12) | 0.9176 (4) | 0.3529 (3) | 0.0227 (10) | |
C12 | −0.0705 (12) | 0.9253 (4) | 0.2676 (3) | 0.0232 (10) | |
H12 | −0.1906 | 0.9882 | 0.2386 | 0.028* | |
Br13 | −0.04126 (13) | 0.84563 (5) | 0.11182 (3) | 0.02951 (17) | |
C13 | 0.0476 (12) | 0.8394 (4) | 0.2264 (3) | 0.0229 (10) | |
O14 | 0.3444 (9) | 0.6603 (3) | 0.2300 (2) | 0.0320 (9) | |
H14 | 0.2966 | 0.6726 | 0.1792 | 0.048* | |
C14 | 0.2266 (11) | 0.7469 (4) | 0.2676 (3) | 0.0228 (10) | |
Br15 | 0.51745 (13) | 0.61547 (4) | 0.41019 (3) | 0.02696 (17) | |
C15 | 0.2814 (12) | 0.7423 (4) | 0.3526 (3) | 0.0240 (11) | |
C16 | 0.1678 (12) | 0.8260 (4) | 0.3959 (3) | 0.0220 (10) | |
H16 | 0.2092 | 0.8214 | 0.4537 | 0.026* | |
N17 | −0.2474 (12) | 1.0800 (4) | 0.4266 (3) | 0.0336 (11) | |
C17 | −0.1384 (12) | 1.0078 (4) | 0.3959 (3) | 0.0254 (11) | |
C21 | 0.8384 (11) | 0.4237 (4) | 0.1469 (3) | 0.0208 (10) | |
C22 | 0.8960 (12) | 0.4265 (4) | 0.2305 (3) | 0.0227 (10) | |
H22 | 0.8098 | 0.4868 | 0.2571 | 0.027* | |
Br23 | 1.17513 (13) | 0.33922 (4) | 0.38743 (3) | 0.02710 (17) | |
C23 | 1.0847 (12) | 0.3378 (4) | 0.2736 (3) | 0.0217 (10) | |
O24 | 1.4033 (9) | 0.1624 (3) | 0.2758 (2) | 0.0287 (8) | |
H24 | 1.4262 | 0.1708 | 0.3255 | 0.034* | |
C24 | 1.2159 (11) | 0.2491 (4) | 0.2365 (3) | 0.0209 (10) | |
Br25 | 1.33538 (13) | 0.13119 (4) | 0.09937 (3) | 0.02804 (17) | |
C25 | 1.1513 (11) | 0.2491 (4) | 0.1521 (3) | 0.0207 (10) | |
C26 | 0.9636 (11) | 0.3361 (4) | 0.1071 (3) | 0.0210 (10) | |
H26 | 0.9212 | 0.3358 | 0.0500 | 0.025* | |
N27 | 0.5009 (11) | 0.5912 (4) | 0.0657 (3) | 0.0327 (11) | |
C27 | 0.6505 (12) | 0.5170 (4) | 0.1000 (3) | 0.0243 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.027 (2) | 0.022 (3) | 0.020 (2) | −0.001 (2) | −0.0030 (18) | −0.0080 (19) |
C12 | 0.026 (2) | 0.024 (3) | 0.020 (2) | 0.000 (2) | −0.0070 (18) | −0.0025 (19) |
Br13 | 0.0399 (3) | 0.0331 (3) | 0.0167 (3) | 0.0045 (2) | −0.0087 (2) | −0.0093 (2) |
C13 | 0.029 (2) | 0.023 (3) | 0.019 (2) | −0.004 (2) | −0.0043 (18) | −0.0070 (19) |
O14 | 0.047 (2) | 0.027 (2) | 0.0227 (19) | 0.0064 (17) | −0.0078 (16) | −0.0115 (16) |
C14 | 0.028 (3) | 0.020 (3) | 0.022 (3) | 0.000 (2) | −0.0007 (19) | −0.010 (2) |
Br15 | 0.0355 (3) | 0.0207 (3) | 0.0235 (3) | 0.0042 (2) | −0.0071 (2) | −0.0029 (2) |
C15 | 0.025 (2) | 0.024 (3) | 0.022 (2) | −0.004 (2) | −0.0064 (18) | 0.002 (2) |
C16 | 0.029 (2) | 0.022 (3) | 0.017 (2) | −0.002 (2) | −0.0032 (18) | −0.0076 (19) |
N17 | 0.049 (3) | 0.027 (3) | 0.026 (2) | 0.009 (2) | −0.013 (2) | −0.009 (2) |
C17 | 0.034 (3) | 0.022 (3) | 0.022 (3) | 0.003 (2) | −0.012 (2) | −0.006 (2) |
C21 | 0.021 (2) | 0.021 (3) | 0.021 (2) | −0.0004 (19) | −0.0036 (17) | −0.0052 (19) |
C22 | 0.028 (2) | 0.021 (3) | 0.020 (2) | 0.000 (2) | −0.0002 (18) | −0.0093 (19) |
Br23 | 0.0360 (3) | 0.0303 (3) | 0.0166 (3) | −0.0001 (2) | −0.00651 (19) | −0.0078 (2) |
C23 | 0.024 (2) | 0.029 (3) | 0.013 (2) | −0.007 (2) | −0.0007 (17) | −0.0036 (19) |
O24 | 0.039 (2) | 0.026 (2) | 0.0206 (18) | 0.0079 (16) | −0.0116 (15) | −0.0072 (15) |
C24 | 0.022 (2) | 0.022 (3) | 0.020 (2) | −0.0031 (19) | −0.0022 (17) | −0.0031 (19) |
Br25 | 0.0358 (3) | 0.0261 (3) | 0.0231 (3) | 0.0066 (2) | −0.0054 (2) | −0.0114 (2) |
C25 | 0.025 (2) | 0.024 (3) | 0.015 (2) | −0.003 (2) | −0.0007 (17) | −0.0075 (19) |
C26 | 0.022 (2) | 0.028 (3) | 0.013 (2) | −0.001 (2) | −0.0043 (17) | −0.0043 (19) |
N27 | 0.042 (3) | 0.031 (3) | 0.024 (2) | 0.006 (2) | −0.0052 (19) | −0.008 (2) |
C27 | 0.033 (3) | 0.025 (3) | 0.015 (2) | 0.000 (2) | −0.003 (2) | −0.004 (2) |
C11—C16 | 1.394 (7) | C21—C22 | 1.394 (7) |
C11—C12 | 1.401 (7) | C21—C26 | 1.392 (7) |
C11—C17 | 1.452 (7) | C21—C27 | 1.453 (6) |
C12—C13 | 1.381 (7) | C22—C23 | 1.391 (7) |
C12—H12 | 0.9500 | C22—H22 | 0.9500 |
Br13—C13 | 1.895 (5) | Br23—C23 | 1.903 (5) |
C13—C14 | 1.392 (7) | C23—C24 | 1.385 (7) |
O14—C14 | 1.355 (6) | O24—C24 | 1.347 (5) |
O14—H14 | 0.8400 | O24—H24 | 0.8400 |
C14—C15 | 1.395 (7) | C24—C25 | 1.406 (6) |
Br15—C15 | 1.899 (5) | Br25—C25 | 1.880 (5) |
C15—C16 | 1.375 (7) | C25—C26 | 1.387 (6) |
C16—H16 | 0.9500 | C26—H26 | 0.9500 |
N17—C17 | 1.133 (7) | N27—C27 | 1.136 (6) |
C16—C11—C12 | 121.3 (5) | C22—C21—C26 | 121.9 (4) |
C16—C11—C17 | 120.5 (4) | C22—C21—C27 | 118.2 (5) |
C12—C11—C17 | 118.2 (4) | C26—C21—C27 | 119.9 (4) |
C13—C12—C11 | 118.6 (5) | C23—C22—C21 | 117.4 (5) |
C13—C12—H12 | 120.7 | C23—C22—H22 | 121.3 |
C11—C12—H12 | 120.7 | C21—C22—H22 | 121.3 |
C12—C13—C14 | 121.4 (5) | C24—C23—C22 | 122.6 (4) |
C12—C13—Br13 | 119.6 (4) | C24—C23—Br23 | 118.5 (4) |
C14—C13—Br13 | 118.9 (4) | C22—C23—Br23 | 118.8 (4) |
C14—O14—H14 | 109.5 | C24—O24—H24 | 109.5 |
O14—C14—C13 | 123.5 (4) | O24—C24—C23 | 124.4 (4) |
O14—C14—C15 | 118.3 (4) | O24—C24—C25 | 117.4 (4) |
C13—C14—C15 | 118.2 (5) | C23—C24—C25 | 118.2 (4) |
C16—C15—C14 | 122.2 (5) | C26—C25—C24 | 120.7 (4) |
C16—C15—Br15 | 119.2 (4) | C26—C25—Br25 | 120.2 (4) |
C14—C15—Br15 | 118.6 (4) | C24—C25—Br25 | 119.1 (4) |
C15—C16—C11 | 118.3 (4) | C25—C26—C21 | 119.1 (4) |
C15—C16—H16 | 120.9 | C25—C26—H26 | 120.5 |
C11—C16—H16 | 120.9 | C21—C26—H26 | 120.5 |
N17—C17—C11 | 176.9 (5) | N27—C27—C21 | 177.8 (5) |
C7H3I2NO | Z = 4 |
Mr = 370.90 | F(000) = 664 |
Triclinic, P1 | Dx = 2.846 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.648 (2) Å | Cell parameters from 2025 reflections |
b = 9.393 (2) Å | θ = 2.6–27.5° |
c = 12.120 (2) Å | µ = 7.21 mm−1 |
α = 97.32 (1)° | T = 174 K |
β = 109.86 (1)° | Prism, colorless |
γ = 105.59 (1)° | 0.30 × 0.25 × 0.20 mm |
V = 865.5 (3) Å3 |
Siemens area detector diffractometer | 3930 independent reflections |
Radiation source: fine-focus sealed tube | 3102 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ω scans | θmax = 27.0°, θmin = 1.8° |
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995' | h = −11→11 |
Tmin = 0.121, Tmax = 0.237 | k = −12→12 |
10284 measured reflections | l = −15→15 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.031P)2 + 5.03P] where P = (Fo2 + 2Fc2)/3 |
3930 reflections | (Δ/σ)max = 0.001 |
334 parameters | Δρmax = 1.08 e Å−3 |
220 restraints | Δρmin = −1.24 e Å−3 |
C7H3I2NO | γ = 105.59 (1)° |
Mr = 370.90 | V = 865.5 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.648 (2) Å | Mo Kα radiation |
b = 9.393 (2) Å | µ = 7.21 mm−1 |
c = 12.120 (2) Å | T = 174 K |
α = 97.32 (1)° | 0.30 × 0.25 × 0.20 mm |
β = 109.86 (1)° |
Siemens area detector diffractometer | 3930 independent reflections |
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995' | 3102 reflections with I > 2σ(I) |
Tmin = 0.121, Tmax = 0.237 | Rint = 0.038 |
10284 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 220 restraints |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.14 | Δρmax = 1.08 e Å−3 |
3930 reflections | Δρmin = −1.24 e Å−3 |
334 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C11 | 0.3419 (5) | 0.5807 (7) | 0.7810 (6) | 0.0190 (16) | 0.9568 (18) |
C12 | 0.2741 (4) | 0.6649 (7) | 0.7047 (6) | 0.0198 (17) | 0.9568 (18) |
H12 | 0.2521 | 0.7513 | 0.7374 | 0.024* | 0.9568 (18) |
I13 | 0.13338 (8) | 0.75915 (8) | 0.46927 (6) | 0.02092 (18) | 0.9568 (18) |
C13 | 0.2370 (8) | 0.6287 (8) | 0.5834 (7) | 0.0159 (15) | 0.9568 (18) |
O14 | 0.2305 (7) | 0.4560 (6) | 0.4128 (5) | 0.0261 (14) | 0.9568 (18) |
H14 | 0.1858 | 0.5141 | 0.3760 | 0.031* | 0.9568 (18) |
C14 | 0.2692 (9) | 0.5027 (8) | 0.5347 (7) | 0.0176 (16) | 0.9568 (18) |
I15 | 0.38083 (8) | 0.22502 (7) | 0.53200 (6) | 0.02361 (18) | 0.9568 (18) |
C15 | 0.3394 (9) | 0.4168 (8) | 0.6092 (7) | 0.0177 (16) | 0.9568 (18) |
C16 | 0.3783 (9) | 0.4552 (8) | 0.7340 (7) | 0.0205 (17) | 0.9568 (18) |
H16 | 0.4282 | 0.3971 | 0.7854 | 0.025* | 0.9568 (18) |
N17 | 0.4085 (10) | 0.6505 (9) | 1.0075 (7) | 0.030 (2) | 0.9568 (18) |
C17 | 0.3802 (9) | 0.6188 (9) | 0.9083 (8) | 0.0235 (18) | 0.9568 (18) |
C21 | 0.1590 (9) | 0.2865 (8) | 0.0842 (7) | 0.0183 (16) | 0.9568 (18) |
C22 | 0.2294 (9) | 0.2059 (8) | 0.1664 (7) | 0.0196 (17) | 0.9568 (18) |
H22 | 0.2508 | 0.2366 | 0.2495 | 0.024* | 0.9568 (18) |
I23 | 0.37373 (8) | −0.04516 (8) | 0.24151 (6) | 0.0246 (2) | 0.9568 (18) |
C23 | 0.2675 (9) | 0.0802 (8) | 0.1243 (7) | 0.0182 (16) | 0.9568 (18) |
O24 | 0.2713 (7) | −0.0887 (6) | −0.0453 (5) | 0.0290 (14) | 0.9568 (18) |
H24 | 0.3140 | −0.1288 | 0.0105 | 0.035* | 0.9568 (18) |
C24 | 0.2351 (9) | 0.0348 (8) | 0.0013 (7) | 0.0185 (16) | 0.9568 (18) |
I25 | 0.11671 (9) | 0.04370 (8) | −0.26068 (5) | 0.02799 (19) | 0.9568 (18) |
C25 | 0.1650 (9) | 0.1154 (8) | −0.0784 (6) | 0.0169 (15) | 0.9568 (18) |
C26 | 0.1262 (9) | 0.2417 (9) | −0.0361 (7) | 0.0225 (18) | 0.9568 (18) |
H26 | 0.0770 | 0.2966 | −0.0909 | 0.027* | 0.9568 (18) |
N27 | 0.0879 (11) | 0.5155 (9) | 0.1669 (8) | 0.040 (3) | 0.9568 (18) |
C27 | 0.1213 (10) | 0.4167 (10) | 0.1291 (8) | 0.030 (2) | 0.9568 (18) |
C11A | 0.342 (2) | 0.882 (3) | 1.0711 (18) | 0.019* | 0.0207 (10) |
C12A | 0.274 (2) | 0.969 (2) | 0.997 (2) | 0.019* | 0.0207 (10) |
H12A | 0.2537 | 1.0549 | 1.0318 | 0.023* | 0.0207 (10) |
I13A | 0.1340 (19) | 1.070 (2) | 0.765 (3) | 0.021* | 0.0207 (10) |
C13A | 0.2356 (18) | 0.935 (2) | 0.876 (2) | 0.017* | 0.0207 (10) |
O14A | 0.2300 (19) | 0.769 (2) | 0.7022 (17) | 0.026* | 0.0207 (10) |
H14A | 0.1855 | 0.8278 | 0.6669 | 0.031* | 0.0207 (10) |
C14A | 0.2655 (18) | 0.810 (2) | 0.8240 (18) | 0.017* | 0.0207 (10) |
I15A | 0.3762 (17) | 0.532 (2) | 0.815 (2) | 0.024* | 0.0207 (10) |
C15A | 0.3336 (19) | 0.721 (2) | 0.8959 (18) | 0.018* | 0.0207 (10) |
C16A | 0.373 (2) | 0.755 (3) | 1.0209 (18) | 0.020* | 0.0207 (10) |
H16A | 0.4198 | 0.6940 | 1.0702 | 0.024* | 0.0207 (10) |
N17A | 0.411 (3) | 0.951 (6) | 1.298 (2) | 0.031* | 0.0207 (10) |
C17A | 0.383 (2) | 0.918 (3) | 1.1988 (19) | 0.022* | 0.0207 (10) |
C21A | 0.1703 (19) | 0.578 (2) | 0.381 (2) | 0.020* | 0.0207 (10) |
C22A | 0.239 (2) | 0.499 (3) | 0.464 (2) | 0.020* | 0.0207 (10) |
H22A | 0.2615 | 0.5320 | 0.5474 | 0.024* | 0.0207 (10) |
I23A | 0.3789 (19) | 0.247 (3) | 0.543 (2) | 0.025* | 0.0207 (10) |
C23A | 0.2749 (19) | 0.371 (3) | 0.4240 (19) | 0.018* | 0.0207 (10) |
O24A | 0.2750 (19) | 0.196 (2) | 0.256 (2) | 0.029* | 0.0207 (10) |
H24A | 0.3174 | 0.1573 | 0.3127 | 0.035* | 0.0207 (10) |
C24A | 0.2420 (18) | 0.323 (2) | 0.3012 (19) | 0.019* | 0.0207 (10) |
I25A | 0.1245 (19) | 0.326 (3) | 0.0381 (18) | 0.028* | 0.0207 (10) |
C25A | 0.1738 (18) | 0.402 (2) | 0.2201 (19) | 0.017* | 0.0207 (10) |
C26A | 0.1380 (19) | 0.531 (2) | 0.261 (2) | 0.023* | 0.0207 (10) |
H26A | 0.0912 | 0.5864 | 0.2052 | 0.028* | 0.0207 (10) |
N27A | 0.109 (3) | 0.813 (3) | 0.465 (5) | 0.040* | 0.0207 (10) |
C27A | 0.134 (2) | 0.711 (3) | 0.424 (3) | 0.029* | 0.0207 (10) |
C11B | 0.333 (2) | 0.322 (4) | 0.511 (2) | 0.019* | 0.0225 (12) |
C12B | 0.265 (2) | 0.404 (3) | 0.433 (2) | 0.019* | 0.0225 (12) |
H12B | 0.2427 | 0.4910 | 0.4647 | 0.023* | 0.0225 (12) |
I13B | 0.1246 (19) | 0.493 (3) | 0.196 (3) | 0.021* | 0.0225 (12) |
C13B | 0.229 (2) | 0.366 (3) | 0.312 (2) | 0.017* | 0.0225 (12) |
O14B | 0.228 (2) | 0.192 (3) | 0.145 (2) | 0.026* | 0.0225 (12) |
H14B | 0.1834 | 0.2497 | 0.1066 | 0.031* | 0.0225 (12) |
C14B | 0.261 (2) | 0.239 (3) | 0.266 (2) | 0.017* | 0.0225 (12) |
I15B | 0.376 (2) | −0.037 (3) | 0.268 (4) | 0.024* | 0.0225 (12) |
C15B | 0.330 (2) | 0.153 (3) | 0.342 (3) | 0.018* | 0.0225 (12) |
C16B | 0.367 (2) | 0.194 (3) | 0.466 (3) | 0.020* | 0.0225 (12) |
H16B | 0.4135 | 0.1351 | 0.5182 | 0.024* | 0.0225 (12) |
N17B | 0.398 (3) | 0.400 (7) | 0.737 (2) | 0.031* | 0.0225 (12) |
C17B | 0.371 (2) | 0.362 (4) | 0.639 (2) | 0.022* | 0.0225 (12) |
C21B | 0.164 (2) | 0.016 (3) | −0.173 (4) | 0.020* | 0.0225 (12) |
C22B | 0.233 (2) | −0.066 (3) | −0.092 (3) | 0.020* | 0.0225 (12) |
H22B | 0.2567 | −0.0354 | −0.0088 | 0.024* | 0.0225 (12) |
I23B | 0.369 (2) | −0.323 (3) | −0.020 (3) | 0.025* | 0.0225 (12) |
C23B | 0.267 (2) | −0.194 (3) | −0.136 (3) | 0.018* | 0.0225 (12) |
O24B | 0.264 (2) | −0.365 (3) | −0.307 (3) | 0.029* | 0.0225 (12) |
H24B | 0.3068 | −0.4055 | −0.2518 | 0.035* | 0.0225 (12) |
C24B | 0.233 (2) | −0.239 (3) | −0.259 (3) | 0.019* | 0.0225 (12) |
I25B | 0.116 (3) | −0.227 (5) | −0.520 (3) | 0.028* | 0.0225 (12) |
C25B | 0.165 (2) | −0.157 (4) | −0.338 (3) | 0.017* | 0.0225 (12) |
C26B | 0.131 (2) | −0.028 (4) | −0.294 (4) | 0.023* | 0.0225 (12) |
H26B | 0.0838 | 0.0287 | −0.3479 | 0.028* | 0.0225 (12) |
N27B | 0.106 (3) | 0.249 (3) | −0.084 (6) | 0.040* | 0.0225 (12) |
C27B | 0.130 (3) | 0.147 (3) | −0.127 (5) | 0.029* | 0.0225 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.018 (4) | 0.025 (4) | 0.019 (4) | 0.011 (4) | 0.009 (3) | 0.009 (3) |
C12 | 0.022 (4) | 0.008 (4) | 0.022 (4) | 0.000 (3) | 0.005 (3) | −0.004 (3) |
I13 | 0.0259 (3) | 0.0207 (3) | 0.0210 (3) | 0.0133 (3) | 0.0092 (2) | 0.0094 (2) |
C13 | 0.020 (4) | 0.016 (4) | 0.019 (4) | 0.011 (3) | 0.010 (3) | 0.011 (3) |
O14 | 0.046 (4) | 0.026 (3) | 0.016 (3) | 0.024 (3) | 0.013 (3) | 0.010 (2) |
C14 | 0.020 (4) | 0.021 (4) | 0.014 (3) | 0.006 (3) | 0.008 (3) | 0.008 (3) |
I15 | 0.0331 (3) | 0.0213 (3) | 0.0221 (3) | 0.0168 (3) | 0.0113 (2) | 0.0062 (2) |
C15 | 0.021 (4) | 0.015 (4) | 0.022 (4) | 0.008 (3) | 0.012 (3) | 0.008 (3) |
C16 | 0.016 (4) | 0.014 (4) | 0.028 (4) | 0.006 (3) | 0.003 (3) | 0.006 (3) |
N17 | 0.047 (5) | 0.032 (5) | 0.018 (4) | 0.024 (4) | 0.013 (4) | 0.005 (3) |
C17 | 0.025 (4) | 0.017 (4) | 0.031 (5) | 0.013 (4) | 0.007 (4) | 0.010 (4) |
C21 | 0.024 (4) | 0.013 (4) | 0.015 (4) | 0.007 (3) | 0.005 (3) | −0.001 (3) |
C22 | 0.019 (4) | 0.021 (4) | 0.022 (4) | 0.009 (4) | 0.010 (3) | 0.007 (3) |
I23 | 0.0337 (3) | 0.0256 (3) | 0.0193 (4) | 0.0179 (3) | 0.0084 (3) | 0.0094 (3) |
C23 | 0.022 (4) | 0.019 (4) | 0.019 (4) | 0.011 (4) | 0.010 (3) | 0.006 (3) |
O24 | 0.047 (4) | 0.031 (3) | 0.023 (3) | 0.032 (3) | 0.015 (3) | 0.010 (3) |
C24 | 0.017 (4) | 0.017 (4) | 0.023 (4) | 0.008 (3) | 0.007 (3) | 0.011 (3) |
I25 | 0.0399 (4) | 0.0342 (4) | 0.0184 (3) | 0.0229 (3) | 0.0124 (3) | 0.0095 (3) |
C25 | 0.014 (4) | 0.015 (4) | 0.016 (4) | 0.000 (3) | 0.002 (3) | 0.004 (3) |
C26 | 0.021 (4) | 0.026 (4) | 0.024 (4) | 0.011 (4) | 0.006 (3) | 0.016 (4) |
N27 | 0.073 (7) | 0.041 (5) | 0.021 (5) | 0.042 (5) | 0.017 (4) | 0.014 (4) |
C27 | 0.039 (5) | 0.040 (5) | 0.021 (4) | 0.022 (5) | 0.011 (4) | 0.021 (4) |
C11—C12 | 1.375 (10) | C21A—C26A | 1.372 (11) |
C11—C16 | 1.401 (10) | C21A—C22A | 1.401 (11) |
C11—C17 | 1.437 (11) | C21A—C27A | 1.437 (12) |
C12—C13 | 1.369 (10) | C22A—C23A | 1.390 (10) |
C12—H12 | 0.9500 | C22A—H22A | 0.9500 |
I13—C13 | 2.097 (7) | I23A—C23A | 2.090 (7) |
C13—C14 | 1.392 (10) | C23A—C24A | 1.404 (10) |
O14—C14 | 1.380 (8) | O24A—C24A | 1.383 (9) |
O14—H14 | 0.8400 | O24A—H24A | 0.8400 |
C14—C15 | 1.383 (10) | C24A—C25A | 1.382 (10) |
I15—C15 | 2.096 (7) | I25A—C25A | 2.087 (7) |
C15—C16 | 1.408 (11) | C25A—C26A | 1.399 (11) |
C16—H16 | 0.9500 | C26A—H26A | 0.9500 |
N17—C17 | 1.125 (11) | N27A—C27A | 1.131 (12) |
C21—C26 | 1.372 (11) | C11B—C12B | 1.375 (10) |
C21—C22 | 1.401 (11) | C11B—C16B | 1.401 (10) |
C21—C27 | 1.437 (12) | C11B—C17B | 1.438 (11) |
C22—C23 | 1.390 (10) | C12B—C13B | 1.369 (10) |
C22—H22 | 0.9500 | C12B—H12B | 0.9500 |
I23—C23 | 2.090 (7) | I13B—C13B | 2.097 (7) |
C23—C24 | 1.404 (10) | C13B—C14B | 1.392 (10) |
O24—C24 | 1.383 (9) | O14B—C14B | 1.380 (9) |
O24—H24 | 0.8400 | O14B—H14B | 0.8400 |
C24—C25 | 1.382 (10) | C14B—C15B | 1.383 (10) |
I25—C25 | 2.087 (7) | I15B—C15B | 2.096 (7) |
C25—C26 | 1.399 (11) | C15B—C16B | 1.408 (11) |
C26—H26 | 0.9500 | C16B—H16B | 0.9500 |
N27—C27 | 1.131 (12) | N17B—C17B | 1.125 (11) |
C11A—C12A | 1.375 (10) | C21B—C26B | 1.372 (11) |
C11A—C16A | 1.401 (10) | C21B—C22B | 1.401 (11) |
C11A—C17A | 1.438 (11) | C21B—C27B | 1.437 (12) |
C12A—C13A | 1.369 (10) | C22B—C23B | 1.390 (10) |
C12A—H12A | 0.9500 | C22B—H22B | 0.9500 |
I13A—C13A | 2.097 (7) | I23B—C23B | 2.090 (7) |
C13A—C14A | 1.392 (10) | C23B—C24B | 1.404 (10) |
O14A—C14A | 1.380 (9) | O24B—C24B | 1.383 (9) |
O14A—H14A | 0.8400 | O24B—H24B | 0.8400 |
C14A—C15A | 1.383 (10) | C24B—C25B | 1.382 (10) |
I15A—C15A | 2.096 (7) | I25B—C25B | 2.086 (7) |
C15A—C16A | 1.408 (11) | C25B—C26B | 1.399 (11) |
C16A—H16A | 0.9500 | C26B—H26B | 0.9500 |
N17A—C17A | 1.125 (11) | N27B—C27B | 1.131 (12) |
C12—C11—C16 | 119.2 (7) | C26A—C21A—C22A | 120.8 (7) |
C12—C11—C17 | 122.2 (6) | C26A—C21A—C27A | 120.9 (8) |
C16—C11—C17 | 118.6 (7) | C22A—C21A—C27A | 118.3 (7) |
C13—C12—C11 | 122.3 (6) | C23A—C22A—C21A | 118.9 (7) |
C13—C12—H12 | 118.8 | C23A—C22A—H22A | 120.5 |
C11—C12—H12 | 118.8 | C21A—C22A—H22A | 120.5 |
C12—C13—C14 | 119.3 (6) | C22A—C23A—C24A | 120.3 (7) |
C12—C13—I13 | 121.5 (5) | C22A—C23A—I23A | 121.1 (5) |
C14—C13—I13 | 119.2 (5) | C24A—C23A—I23A | 118.6 (5) |
C14—O14—H14 | 109.5 | C24A—O24A—H24A | 109.5 |
O14—C14—C15 | 117.4 (6) | C25A—C24A—O24A | 117.3 (7) |
O14—C14—C13 | 122.8 (6) | C25A—C24A—C23A | 119.9 (7) |
C15—C14—C13 | 119.8 (7) | O24A—C24A—C23A | 122.8 (6) |
C14—C15—C16 | 120.7 (7) | C24A—C25A—C26A | 119.8 (7) |
C14—C15—I15 | 118.7 (5) | C24A—C25A—I25A | 118.8 (5) |
C16—C15—I15 | 120.6 (5) | C26A—C25A—I25A | 121.4 (5) |
C11—C16—C15 | 118.7 (7) | C21A—C26A—C25A | 120.3 (7) |
C11—C16—H16 | 120.6 | C21A—C26A—H26A | 119.9 |
C15—C16—H16 | 120.6 | C25A—C26A—H26A | 119.9 |
N17—C17—C11 | 178.7 (8) | N27A—C27A—C21A | 176 (2) |
C26—C21—C22 | 120.8 (7) | C12B—C11B—C16B | 119.2 (7) |
C26—C21—C27 | 120.9 (7) | C12B—C11B—C17B | 122.2 (7) |
C22—C21—C27 | 118.3 (7) | C16B—C11B—C17B | 118.6 (7) |
C23—C22—C21 | 118.9 (7) | C13B—C12B—C11B | 122.3 (6) |
C23—C22—H22 | 120.5 | C13B—C12B—H12B | 118.8 |
C21—C22—H22 | 120.5 | C11B—C12B—H12B | 118.8 |
C22—C23—C24 | 120.3 (7) | C12B—C13B—C14B | 119.3 (6) |
C22—C23—I23 | 121.1 (5) | C12B—C13B—I13B | 121.5 (5) |
C24—C23—I23 | 118.6 (5) | C14B—C13B—I13B | 119.2 (5) |
C24—O24—H24 | 109.5 | C14B—O14B—H14B | 109.5 |
C25—C24—O24 | 117.3 (7) | O14B—C14B—C15B | 117.4 (6) |
C25—C24—C23 | 119.9 (7) | O14B—C14B—C13B | 122.8 (6) |
O24—C24—C23 | 122.8 (6) | C15B—C14B—C13B | 119.8 (7) |
C24—C25—C26 | 119.8 (7) | C14B—C15B—C16B | 120.7 (7) |
C24—C25—I25 | 118.8 (5) | C14B—C15B—I15B | 118.7 (5) |
C26—C25—I25 | 121.4 (5) | C16B—C15B—I15B | 120.7 (5) |
C21—C26—C25 | 120.3 (7) | C11B—C16B—C15B | 118.7 (7) |
C21—C26—H26 | 119.9 | C11B—C16B—H16B | 120.6 |
C25—C26—H26 | 119.9 | C15B—C16B—H16B | 120.6 |
N27—C27—C21 | 177.1 (9) | N17B—C17B—C11B | 177 (3) |
C12A—C11A—C16A | 119.2 (7) | C26B—C21B—C22B | 120.8 (7) |
C12A—C11A—C17A | 122.2 (7) | C26B—C21B—C27B | 120.9 (8) |
C16A—C11A—C17A | 118.6 (7) | C22B—C21B—C27B | 118.3 (7) |
C13A—C12A—C11A | 122.3 (6) | C23B—C22B—C21B | 118.9 (7) |
C13A—C12A—H12A | 118.8 | C23B—C22B—H22B | 120.5 |
C11A—C12A—H12A | 118.8 | C21B—C22B—H22B | 120.5 |
C12A—C13A—C14A | 119.3 (6) | C22B—C23B—C24B | 120.3 (7) |
C12A—C13A—I13A | 121.5 (5) | C22B—C23B—I23B | 121.1 (5) |
C14A—C13A—I13A | 119.2 (5) | C24B—C23B—I23B | 118.6 (5) |
C14A—O14A—H14A | 109.5 | C24B—O24B—H24B | 109.5 |
O14A—C14A—C15A | 117.4 (6) | C25B—C24B—O24B | 117.3 (7) |
O14A—C14A—C13A | 122.8 (6) | C25B—C24B—C23B | 119.9 (7) |
C15A—C14A—C13A | 119.8 (7) | O24B—C24B—C23B | 122.8 (6) |
C14A—C15A—C16A | 120.7 (7) | C24B—C25B—C26B | 119.8 (7) |
C14A—C15A—I15A | 118.7 (5) | C24B—C25B—I25B | 118.8 (5) |
C16A—C15A—I15A | 120.7 (5) | C26B—C25B—I25B | 121.4 (5) |
C11A—C16A—C15A | 118.7 (7) | C21B—C26B—C25B | 120.3 (7) |
C11A—C16A—H16A | 120.6 | C21B—C26B—H26B | 119.9 |
C15A—C16A—H16A | 120.6 | C25B—C26B—H26B | 119.9 |
N17A—C17A—C11A | 177 (2) | N27B—C27B—C21B | 176 (2) |
C7H3I2NO | F(000) = 1328 |
Mr = 370.90 | Dx = 2.841 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3574 reflections |
a = 15.657 (4) Å | θ = 2.6–27.5° |
b = 14.320 (4) Å | µ = 7.21 mm−1 |
c = 7.724 (2) Å | T = 173 K |
β = 91.90 (1)° | Needle, colorless |
V = 1730.8 (8) Å3 | 0.50 × 0.10 × 0.07 mm |
Z = 8 |
Siemens area detector diffractometer | 3931 independent reflections |
Radiation source: fine-focus sealed tube | 3587 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ω scans | θmax = 27.5°, θmin = 1.3° |
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995' | h = −20→20 |
Tmin = 0.47, Tmax = 0.60 | k = −17→18 |
16090 measured reflections | l = −10→10 |
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)] = 0.020 | H-atom parameters constrained |
wR(F2) = 0.046 | w = 1/[σ2(Fo2) + (0.014P)2 + 1.59P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.006 |
3936 reflections | Δρmax = 0.60 e Å−3 |
200 parameters | Δρmin = −0.54 e Å−3 |
0 restraints | Extinction correction: SHELXTL |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00378 (9) |
C7H3I2NO | V = 1730.8 (8) Å3 |
Mr = 370.90 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.657 (4) Å | µ = 7.21 mm−1 |
b = 14.320 (4) Å | T = 173 K |
c = 7.724 (2) Å | 0.50 × 0.10 × 0.07 mm |
β = 91.90 (1)° |
Siemens area detector diffractometer | 3931 independent reflections |
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995' | 3587 reflections with I > 2σ(I) |
Tmin = 0.47, Tmax = 0.60 | Rint = 0.038 |
16090 measured reflections |
R[F2 > 2σ(F2)] = 0.020 | 0 restraints |
wR(F2) = 0.046 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.60 e Å−3 |
3936 reflections | Δρmin = −0.54 e Å−3 |
200 parameters |
x | y | z | Uiso*/Ueq | ||
I13 | 0.646356 (10) | 0.465381 (13) | 0.63572 (2) | 0.02125 (6) | |
I15 | 0.349835 (11) | 0.687241 (12) | 0.88878 (2) | 0.02308 (6) | |
O14 | 0.52408 (12) | 0.63736 (13) | 0.7359 (2) | 0.0248 (4) | |
H14 | 0.5761 | 0.6281 | 0.7184 | 0.030* | |
N17 | 0.32264 (16) | 0.23472 (18) | 0.9129 (4) | 0.0354 (6) | |
C11 | 0.39844 (16) | 0.38959 (18) | 0.8398 (3) | 0.0189 (5) | |
C12 | 0.47917 (15) | 0.38600 (19) | 0.7684 (3) | 0.0189 (5) | |
H12 | 0.5043 | 0.3274 | 0.7429 | 0.023* | |
C13 | 0.52267 (15) | 0.46812 (18) | 0.7347 (3) | 0.0174 (5) | |
C14 | 0.48550 (16) | 0.55495 (18) | 0.7689 (3) | 0.0179 (5) | |
C15 | 0.40463 (15) | 0.55699 (17) | 0.8405 (3) | 0.0167 (5) | |
C16 | 0.36027 (15) | 0.47558 (19) | 0.8771 (3) | 0.0181 (5) | |
H16 | 0.3055 | 0.4781 | 0.9261 | 0.022* | |
C17 | 0.35481 (17) | 0.3039 (2) | 0.8807 (4) | 0.0246 (6) | |
I23 | 1.138156 (11) | 0.827849 (13) | 0.60680 (2) | 0.02323 (6) | |
I25 | 0.847294 (11) | 1.048985 (13) | 0.89008 (2) | 0.02429 (6) | |
O24 | 1.01711 (12) | 1.00074 (13) | 0.7181 (3) | 0.0262 (4) | |
H24 | 1.0643 | 0.9914 | 0.6725 | 0.039* | |
N27 | 0.82339 (16) | 0.59508 (18) | 0.9021 (3) | 0.0319 (6) | |
C21 | 0.89493 (16) | 0.75212 (18) | 0.8299 (3) | 0.0192 (5) | |
C22 | 0.97489 (16) | 0.74859 (18) | 0.7543 (3) | 0.0199 (5) | |
H22 | 1.0002 | 0.6901 | 0.7285 | 0.024* | |
C23 | 1.01709 (16) | 0.83144 (19) | 0.7173 (3) | 0.0189 (5) | |
C24 | 0.98030 (16) | 0.91772 (18) | 0.7545 (3) | 0.0188 (5) | |
C25 | 0.90055 (16) | 0.91920 (18) | 0.8323 (3) | 0.0186 (5) | |
C26 | 0.85755 (15) | 0.83761 (19) | 0.8708 (3) | 0.0195 (5) | |
H26 | 0.8037 | 0.8397 | 0.9239 | 0.023* | |
C27 | 0.85282 (16) | 0.6653 (2) | 0.8709 (3) | 0.0241 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
I13 | 0.01725 (9) | 0.02018 (10) | 0.02665 (10) | 0.00015 (6) | 0.00579 (6) | 0.00036 (7) |
I15 | 0.02349 (10) | 0.01406 (10) | 0.03225 (11) | 0.00244 (6) | 0.00940 (7) | 0.00079 (7) |
O14 | 0.0221 (10) | 0.0151 (10) | 0.0380 (11) | −0.0018 (8) | 0.0113 (8) | 0.0012 (8) |
N17 | 0.0341 (14) | 0.0178 (13) | 0.0556 (17) | −0.0033 (11) | 0.0185 (12) | −0.0002 (12) |
C11 | 0.0194 (12) | 0.0147 (13) | 0.0227 (12) | −0.0007 (10) | 0.0012 (10) | −0.0006 (10) |
C12 | 0.0190 (12) | 0.0153 (13) | 0.0226 (12) | 0.0015 (10) | 0.0017 (10) | −0.0005 (10) |
C13 | 0.0132 (11) | 0.0177 (13) | 0.0214 (12) | 0.0010 (10) | 0.0034 (9) | 0.0005 (10) |
C14 | 0.0185 (12) | 0.0162 (13) | 0.0190 (12) | −0.0020 (10) | 0.0008 (9) | 0.0017 (10) |
C15 | 0.0176 (12) | 0.0130 (12) | 0.0196 (12) | 0.0035 (9) | 0.0013 (9) | −0.0011 (10) |
C16 | 0.0184 (12) | 0.0169 (14) | 0.0192 (12) | −0.0018 (10) | 0.0042 (10) | 0.0008 (10) |
C17 | 0.0229 (14) | 0.0179 (15) | 0.0336 (16) | 0.0017 (11) | 0.0094 (12) | −0.0009 (11) |
I23 | 0.01934 (10) | 0.01976 (11) | 0.03114 (11) | −0.00083 (7) | 0.00923 (7) | −0.00137 (7) |
I25 | 0.02248 (10) | 0.01767 (11) | 0.03318 (11) | 0.00277 (7) | 0.00763 (7) | 0.00025 (7) |
O24 | 0.0228 (10) | 0.0170 (10) | 0.0394 (11) | −0.0003 (8) | 0.0110 (8) | 0.0032 (8) |
N27 | 0.0282 (13) | 0.0182 (13) | 0.0496 (15) | −0.0018 (10) | 0.0029 (11) | −0.0017 (11) |
C21 | 0.0188 (12) | 0.0163 (13) | 0.0226 (13) | −0.0023 (10) | 0.0012 (9) | 0.0031 (10) |
C22 | 0.0212 (13) | 0.0144 (13) | 0.0241 (13) | −0.0017 (10) | 0.0008 (10) | −0.0011 (10) |
C23 | 0.0144 (12) | 0.0211 (14) | 0.0214 (12) | 0.0005 (10) | 0.0047 (9) | −0.0008 (10) |
C24 | 0.0197 (12) | 0.0155 (14) | 0.0214 (12) | −0.0017 (10) | 0.0021 (10) | 0.0013 (10) |
C25 | 0.0191 (12) | 0.0168 (13) | 0.0201 (12) | 0.0030 (10) | 0.0018 (9) | −0.0004 (10) |
C26 | 0.0162 (12) | 0.0183 (14) | 0.0242 (13) | −0.0015 (10) | 0.0033 (10) | 0.0015 (10) |
C27 | 0.0196 (14) | 0.0246 (16) | 0.0286 (15) | 0.0021 (11) | 0.0066 (11) | −0.0012 (11) |
I13—C13 | 2.106 (2) | I23—C23 | 2.105 (2) |
I15—C15 | 2.092 (2) | I25—C25 | 2.091 (3) |
O14—C14 | 1.354 (3) | O24—C24 | 1.355 (3) |
O14—H14 | 0.8400 | O24—H24 | 0.8400 |
N17—C17 | 1.143 (4) | N27—C27 | 1.135 (4) |
C11—C12 | 1.397 (3) | C21—C22 | 1.400 (3) |
C11—C16 | 1.403 (4) | C21—C26 | 1.398 (4) |
C11—C17 | 1.444 (4) | C21—C27 | 1.447 (4) |
C12—C13 | 1.388 (4) | C22—C23 | 1.392 (4) |
C12—H12 | 0.9500 | C22—H22 | 0.9500 |
C13—C14 | 1.402 (4) | C23—C24 | 1.397 (4) |
C14—C15 | 1.399 (3) | C24—C25 | 1.404 (3) |
C15—C16 | 1.391 (3) | C25—C26 | 1.386 (4) |
C16—H16 | 0.9500 | C26—H26 | 0.9500 |
C14—O14—H14 | 109.5 | C24—O24—H24 | 109.5 |
C12—C11—C16 | 120.7 (2) | C22—C21—C26 | 120.8 (2) |
C12—C11—C17 | 119.7 (2) | C22—C21—C27 | 118.7 (2) |
C16—C11—C17 | 119.5 (2) | C26—C21—C27 | 120.4 (2) |
C13—C12—C11 | 119.9 (2) | C23—C22—C21 | 119.5 (2) |
C13—C12—H12 | 120.0 | C23—C22—H22 | 120.3 |
C11—C12—H12 | 120.0 | C21—C22—H22 | 120.3 |
C12—C13—C14 | 120.5 (2) | C22—C23—C24 | 120.6 (2) |
C12—C13—I13 | 121.01 (19) | C22—C23—I23 | 120.15 (19) |
C14—C13—I13 | 118.53 (18) | C24—C23—I23 | 119.21 (19) |
O14—C14—C15 | 118.1 (2) | O24—C24—C23 | 123.5 (2) |
O14—C14—C13 | 123.2 (2) | O24—C24—C25 | 117.8 (2) |
C15—C14—C13 | 118.7 (2) | C23—C24—C25 | 118.7 (2) |
C16—C15—C14 | 121.8 (2) | C26—C25—C24 | 121.6 (2) |
C16—C15—I15 | 120.04 (18) | C26—C25—I25 | 120.25 (18) |
C14—C15—I15 | 118.11 (18) | C24—C25—I25 | 118.12 (19) |
C15—C16—C11 | 118.4 (2) | C25—C26—C21 | 118.7 (2) |
C15—C16—H16 | 120.8 | C25—C26—H26 | 120.6 |
C11—C16—H16 | 120.8 | C21—C26—H26 | 120.6 |
N17—C17—C11 | 177.9 (3) | N27—C27—C21 | 176.7 (3) |
Experimental details
(MCl) | (MCl-Bz) | (MCl-Xy) | (MBr-A) | |
Crystal data | ||||
Chemical formula | C7H3Cl2NO | C7H3Cl2NO·0.5(C6H6) | C7H3Cl2NO·0.25(C8H10) | C7H3Br2NO |
Mr | 188.00 | 227.06 | 214.55 | 276.92 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 | Monoclinic, P21/n | Triclinic, P1 |
Temperature (K) | 174 | 174 | 174 | 174 |
a, b, c (Å) | 7.3325 (18), 8.999 (2), 12.221 (3) | 7.420 (2), 8.386 (2), 8.808 (2) | 4.5522 (11), 15.067 (4), 13.636 (3) | 8.244 (2), 9.120 (2), 11.687 (3) |
α, β, γ (°) | 78.65 (1), 74.39 (1), 74.23 (1) | 73.82 (1), 66.99 (1), 79.04 (1) | 90, 98.00 (1), 90 | 95.60 (1), 108.55 (1), 106.13 (1) |
V (Å3) | 740.7 (3) | 482.4 (2) | 926.2 (4) | 783.4 (3) |
Z | 4 | 2 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.81 | 0.63 | 0.65 | 10.28 |
Crystal size (mm) | 0.40 × 0.25 × 0.10 | 0.50 × 0.45 × 0.40 | 0.40 × 0.15 × 0.10 | 0.20 × 0.15 × 0.15 |
Data collection | ||||
Diffractometer | Siemens area detector diffractometer | Siemans area detector diffractometer | Siemens area detector diffractometer | Siemens area detector diffractometer |
Absorption correction | Multi-scan SADABS; Sheldrick, 1996; Blessing, 1995' | Multi-scan SADABS; Sheldrick, 1996; Blessing, 1995' | Multi-scan SADABS; Sheldrick, 1996; Blessing, 1995' | Multi-scan SADABS; Sheldrick, 1996; Blessing, 1995' |
Tmin, Tmax | 0.80, 0.92 | 0.74, 0.78 | 0.88, 0.94 | 0.174, 0.214 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8796, 3362, 2309 | 5442, 2141, 2086 | 8934, 1636, 1317 | 9376, 3568, 3107 |
Rint | 0.054 | 0.015 | 0.054 | 0.027 |
(sin θ/λ)max (Å−1) | 0.650 | 0.649 | 0.595 | 0.650 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.095, 1.05 | 0.025, 0.075, 1.08 | 0.048, 0.079, 1.22 | 0.035, 0.079, 1.09 |
No. of reflections | 3362 | 2141 | 1636 | 3568 |
No. of parameters | 199 | 148 | 151 | 200 |
No. of restraints | 0 | 0 | 67 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.28 | 0.46, −0.18 | 0.22, −0.19 | 0.65, −0.61 |
(MBr-B) | (MI-A) | (MI-C) | |
Crystal data | |||
Chemical formula | C7H3Br2NO | C7H3I2NO | C7H3I2NO |
Mr | 276.92 | 370.90 | 370.90 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 | Monoclinic, P21/c |
Temperature (K) | 174 | 174 | 173 |
a, b, c (Å) | 3.9684 (10), 12.669 (3), 16.047 (4) | 8.648 (2), 9.393 (2), 12.120 (2) | 15.657 (4), 14.320 (4), 7.724 (2) |
α, β, γ (°) | 79.68 (1), 83.71 (1), 83.06 (1) | 97.32 (1), 109.86 (1), 105.59 (1) | 90, 91.90 (1), 90 |
V (Å3) | 784.7 (3) | 865.5 (3) | 1730.8 (8) |
Z | 4 | 4 | 8 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 10.26 | 7.21 | 7.21 |
Crystal size (mm) | 0.40 × 0.20 × 0.08 | 0.30 × 0.25 × 0.20 | 0.50 × 0.10 × 0.07 |
Data collection | |||
Diffractometer | Siemens area detector diffractometer | Siemens area detector diffractometer | Siemens area detector diffractometer |
Absorption correction | Multi-scan SADABS; Sheldrick, 1996; Blessing, 1995' | Multi-scan SADABS; Sheldrick, 1996; Blessing, 1995' | Multi-scan SADABS; Sheldrick, 1996; Blessing, 1995' |
Tmin, Tmax | 0.105, 0.440 | 0.121, 0.237 | 0.47, 0.60 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8883, 3510, 2975 | 10284, 3930, 3102 | 16090, 3931, 3587 |
Rint | 0.042 | 0.038 | 0.038 |
(sin θ/λ)max (Å−1) | 0.649 | 0.639 | 0.649 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.120, 1.09 | 0.050, 0.099, 1.14 | 0.020, 0.046, 1.04 |
No. of reflections | 3510 | 3930 | 3936 |
No. of parameters | 200 | 334 | 200 |
No. of restraints | 0 | 220 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.74, −1.61 | 1.08, −1.24 | 0.60, −0.54 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL.