Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803027703/hg6013sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803027703/hg6013Isup2.hkl |
CCDC reference: 231824
Data collection: CrysAlis CCD (UNIL IC & Oxford Diffraction, 2001); cell refinement: CrysAlis RED (UNIL IC & Oxford Diffraction, 2001); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: PLATON.
[CuBr2(C12H8N2)2] | F(000) = 574 |
Mr = 583.76 | Dx = 1.822 Mg m−3 Dm = 1.80 (3) Mg m−3 Dm measured by flotation |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1534 reflections |
a = 9.688 (2) Å | θ = 3.6–24.5° |
b = 9.331 (2) Å | µ = 4.80 mm−1 |
c = 12.034 (2) Å | T = 293 K |
β = 102.04 (3)° | Plate, dark brown |
V = 1063.9 (4) Å3 | 0.30 × 0.15 × 0.15 mm |
Z = 2 |
Kuma KM4-CCD diffractometer | 2439 independent reflections |
Radiation source: CX-Mo12x0.4-S Seifert Mo Tube | 2138 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
Detector resolution: 18.4 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −12→10 |
Absorption correction: numerical (X-RED; Stoe & Cie, 1999) | k = −12→12 |
Tmin = 0.236, Tmax = 0.497 | l = −15→15 |
12944 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.077 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0405P)2 + 0.2911P] where P = (Fo2 + 2Fc2)/3 |
2439 reflections | (Δ/σ)max < 0.001 |
142 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.55 e Å−3 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those 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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.37919 (3) | 0.08178 (3) | 0.31810 (2) | 0.0449 (1) | |
Cu1 | 0.50000 | 0.00000 | 0.50000 | 0.0259 (1) | |
N1 | 0.6737 (2) | 0.1087 (2) | 0.48047 (16) | 0.0285 (6) | |
N2 | 0.8890 (2) | 0.2762 (2) | 0.42013 (19) | 0.0375 (7) | |
C1 | 0.9803 (3) | 0.0700 (3) | 0.3439 (2) | 0.0406 (9) | |
C2 | 0.9722 (3) | −0.0712 (3) | 0.3198 (2) | 0.0439 (9) | |
C3 | 0.8610 (3) | −0.1557 (3) | 0.3454 (2) | 0.0419 (8) | |
C4 | 0.7612 (3) | −0.0972 (3) | 0.3961 (2) | 0.0368 (8) | |
C6 | 0.6058 (3) | 0.3111 (3) | 0.5819 (2) | 0.0382 (8) | |
C7 | 0.6216 (3) | 0.4521 (3) | 0.6098 (2) | 0.0437 (8) | |
C8 | 0.7213 (3) | 0.5378 (3) | 0.5707 (3) | 0.0456 (9) | |
C9 | 0.8067 (3) | 0.4810 (3) | 0.5066 (3) | 0.0445 (9) | |
C11 | 0.8779 (2) | 0.1369 (3) | 0.3970 (2) | 0.0328 (7) | |
C12 | 0.7679 (2) | 0.0496 (3) | 0.4249 (2) | 0.0292 (6) | |
C13 | 0.6909 (2) | 0.2468 (3) | 0.5126 (2) | 0.0297 (7) | |
C14 | 0.7978 (2) | 0.3331 (3) | 0.4772 (2) | 0.0349 (7) | |
H1 | 1.05310 | 0.12440 | 0.32590 | 0.0490* | |
H2 | 1.04010 | −0.11360 | 0.28610 | 0.0530* | |
H3 | 0.85630 | −0.25270 | 0.32730 | 0.0500* | |
H4 | 0.68870 | −0.15390 | 0.41180 | 0.0440* | |
H6 | 0.53910 | 0.25640 | 0.60830 | 0.0460* | |
H7 | 0.56550 | 0.49270 | 0.65540 | 0.0520* | |
H8 | 0.72850 | 0.63470 | 0.58930 | 0.0550* | |
H9 | 0.87190 | 0.53910 | 0.48150 | 0.0530* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0329 (2) | 0.0618 (2) | 0.0399 (2) | 0.0037 (1) | 0.0072 (1) | 0.0143 (1) |
Cu1 | 0.0198 (2) | 0.0282 (2) | 0.0316 (2) | −0.0042 (2) | 0.0100 (2) | 0.0011 (2) |
N1 | 0.0223 (9) | 0.0336 (10) | 0.0312 (10) | −0.0054 (8) | 0.0095 (8) | 0.0003 (8) |
N2 | 0.0295 (11) | 0.0396 (11) | 0.0456 (12) | −0.0074 (9) | 0.0131 (9) | 0.0071 (9) |
C1 | 0.0277 (13) | 0.0573 (17) | 0.0411 (14) | −0.0038 (12) | 0.0173 (11) | 0.0042 (12) |
C2 | 0.0333 (14) | 0.0618 (18) | 0.0399 (14) | 0.0042 (12) | 0.0153 (11) | −0.0042 (13) |
C3 | 0.0365 (13) | 0.0450 (15) | 0.0450 (14) | −0.0025 (12) | 0.0102 (11) | −0.0105 (12) |
C4 | 0.0280 (12) | 0.0407 (13) | 0.0429 (14) | −0.0081 (10) | 0.0099 (11) | −0.0055 (11) |
C6 | 0.0348 (13) | 0.0397 (13) | 0.0424 (14) | −0.0062 (11) | 0.0134 (11) | −0.0041 (11) |
C7 | 0.0426 (15) | 0.0423 (14) | 0.0465 (15) | −0.0015 (12) | 0.0097 (12) | −0.0086 (12) |
C8 | 0.0443 (16) | 0.0318 (12) | 0.0573 (17) | −0.0025 (12) | 0.0027 (13) | −0.0041 (12) |
C9 | 0.0343 (14) | 0.0367 (14) | 0.0616 (18) | −0.0097 (11) | 0.0082 (13) | 0.0058 (13) |
C11 | 0.0216 (11) | 0.0439 (13) | 0.0341 (12) | −0.0062 (10) | 0.0089 (9) | 0.0047 (11) |
C12 | 0.0218 (11) | 0.0370 (11) | 0.0300 (11) | −0.0057 (9) | 0.0081 (9) | 0.0001 (10) |
C13 | 0.0233 (11) | 0.0319 (11) | 0.0336 (12) | −0.0061 (9) | 0.0054 (9) | 0.0016 (9) |
C14 | 0.0268 (12) | 0.0355 (12) | 0.0423 (13) | −0.0064 (10) | 0.0068 (10) | 0.0045 (11) |
Br1—Cu1 | 2.3822 (6) | C7—C8 | 1.408 (4) |
Cu1—N1 | 2.020 (2) | C8—C9 | 1.352 (4) |
Cu1—N1i | 2.020 (2) | C9—C14 | 1.423 (4) |
N1—C12 | 1.356 (3) | C11—C12 | 1.436 (3) |
N1—C13 | 1.346 (3) | C13—C14 | 1.445 (3) |
N2—C11 | 1.329 (3) | C1—H1 | 0.9305 |
N2—C14 | 1.337 (3) | C2—H2 | 0.9301 |
C1—C2 | 1.348 (4) | C3—H3 | 0.9298 |
C1—C11 | 1.431 (4) | C4—H4 | 0.9297 |
C2—C3 | 1.420 (4) | C6—H6 | 0.9299 |
C3—C4 | 1.361 (4) | C7—H7 | 0.9298 |
C4—C12 | 1.411 (4) | C8—H8 | 0.9306 |
C6—C7 | 1.359 (4) | C9—H9 | 0.9294 |
C6—C13 | 1.422 (4) | ||
Br1···N1 | 3.114 (2) | C6···C7iv | 3.597 (4) |
Br1···C12 | 3.729 (2) | C7···C6iv | 3.597 (4) |
Br1···C13 | 3.744 (2) | C7···C7iv | 3.277 (4) |
Br1···N1i | 3.133 (2) | C7···C8iv | 3.571 (4) |
Br1···C3ii | 3.657 (3) | C8···C2x | 3.457 (4) |
Br1···H3ii | 2.9978 | C8···C7iv | 3.571 (4) |
Br1···H1iii | 3.2048 | C8···C3x | 3.479 (4) |
Br1···H8iv | 3.1327 | C11···C2viii | 3.469 (3) |
Br1···H7v | 3.0081 | C11···C3viii | 3.573 (3) |
Cu1···H4 | 2.7093 | C12···C1viii | 3.479 (4) |
Cu1···H6 | 2.7129 | C12···C2viii | 3.549 (3) |
Cu1···H4i | 2.7093 | C3···H8v | 3.0877 |
Cu1···H6i | 2.7129 | C9···H9vii | 3.0927 |
N1···Br1 | 3.114 (2) | H1···Br1xi | 3.2048 |
N1···N2 | 2.820 (3) | H1···H3vi | 2.4818 |
N1···Br1i | 3.133 (2) | H2···N2xii | 2.8982 |
N2···N1 | 2.820 (3) | H3···Br1ix | 2.9978 |
N2···H2vi | 2.8982 | H3···H1xii | 2.4818 |
N2···H9vii | 2.9314 | H4···Cu1 | 2.7093 |
C1···C4viii | 3.586 (4) | H4···H6i | 2.3709 |
C1···C12viii | 3.479 (4) | H6···Cu1 | 2.7129 |
C2···C11viii | 3.469 (3) | H6···H4i | 2.3709 |
C2···C12viii | 3.549 (3) | H7···Br1x | 3.0081 |
C2···C8v | 3.457 (4) | H8···Br1iv | 3.1327 |
C3···Br1ix | 3.657 (3) | H8···C3x | 3.0877 |
C3···C11viii | 3.573 (3) | H9···N2vii | 2.9314 |
C3···C8v | 3.479 (4) | H9···C9vii | 3.0927 |
C4···C1viii | 3.586 (4) | H9···H9vii | 2.5358 |
Br1—Cu1—N1 | 89.64 (6) | C4—C12—C11 | 119.5 (2) |
Br1—Cu1—Br1i | 180.00 | N1—C13—C6 | 121.4 (2) |
Br1—Cu1—N1i | 90.36 (6) | N1—C13—C14 | 120.2 (2) |
Br1i—Cu1—N1 | 90.36 (6) | C6—C13—C14 | 118.5 (2) |
N1—Cu1—N1i | 180.00 | N2—C14—C9 | 120.0 (2) |
Br1i—Cu1—N1i | 89.64 (6) | N2—C14—C13 | 121.4 (2) |
Cu1—N1—C12 | 121.05 (16) | C9—C14—C13 | 118.5 (2) |
Cu1—N1—C13 | 120.24 (15) | C2—C1—H1 | 119.74 |
C12—N1—C13 | 118.4 (2) | C11—C1—H1 | 119.73 |
C11—N2—C14 | 117.6 (2) | C1—C2—H2 | 119.66 |
C2—C1—C11 | 120.5 (3) | C3—C2—H2 | 119.74 |
C1—C2—C3 | 120.6 (3) | C2—C3—H3 | 119.48 |
C2—C3—C4 | 121.1 (3) | C4—C3—H3 | 119.40 |
C3—C4—C12 | 119.9 (3) | C3—C4—H4 | 120.03 |
C7—C6—C13 | 120.3 (3) | C12—C4—H4 | 120.03 |
C6—C7—C8 | 121.1 (3) | C7—C6—H6 | 119.84 |
C7—C8—C9 | 120.8 (3) | C13—C6—H6 | 119.87 |
C8—C9—C14 | 120.6 (3) | C6—C7—H7 | 119.40 |
N2—C11—C1 | 119.1 (2) | C8—C7—H7 | 119.47 |
N2—C11—C12 | 122.5 (2) | C7—C8—H8 | 119.57 |
C1—C11—C12 | 118.3 (2) | C9—C8—H8 | 119.62 |
N1—C12—C4 | 121.0 (2) | C8—C9—H9 | 119.68 |
N1—C12—C11 | 119.6 (2) | C14—C9—H9 | 119.67 |
Br1—Cu1—N1—C12 | −85.48 (17) | C1—C2—C3—C4 | −0.9 (4) |
Br1—Cu1—N1—C13 | 87.88 (17) | C2—C3—C4—C12 | −0.5 (4) |
Br1i—Cu1—N1—C12 | 94.52 (17) | C3—C4—C12—N1 | −176.7 (2) |
Br1i—Cu1—N1—C13 | −92.12 (17) | C3—C4—C12—C11 | 2.0 (4) |
Cu1—N1—C12—C11 | 170.33 (17) | C7—C6—C13—N1 | −177.6 (2) |
C13—N1—C12—C11 | −3.2 (3) | C13—C6—C7—C8 | 0.3 (4) |
Cu1—N1—C13—C6 | 13.5 (3) | C7—C6—C13—C14 | 2.7 (4) |
C12—N1—C13—C6 | −173.0 (2) | C6—C7—C8—C9 | −1.7 (5) |
Cu1—N1—C13—C14 | −166.75 (17) | C7—C8—C9—C14 | 0.0 (5) |
Cu1—N1—C12—C4 | −11.0 (3) | C8—C9—C14—C13 | 3.0 (4) |
C13—N1—C12—C4 | 175.5 (2) | C8—C9—C14—N2 | −175.6 (3) |
C12—N1—C13—C14 | 6.8 (3) | N2—C11—C12—N1 | −2.3 (4) |
C14—N2—C11—C12 | 3.8 (3) | C1—C11—C12—C4 | −2.1 (3) |
C11—N2—C14—C9 | 178.6 (2) | N2—C11—C12—C4 | 179.0 (2) |
C14—N2—C11—C1 | −175.2 (2) | C1—C11—C12—N1 | 176.7 (2) |
C11—N2—C14—C13 | 0.0 (3) | N1—C13—C14—N2 | −5.5 (3) |
C2—C1—C11—C12 | 0.7 (4) | C6—C13—C14—C9 | −4.3 (4) |
C2—C1—C11—N2 | 179.7 (2) | N1—C13—C14—C9 | 176.0 (2) |
C11—C1—C2—C3 | 0.8 (4) | C6—C13—C14—N2 | 174.3 (2) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, y+1/2, −z+1/2; (iii) x−1, y, z; (iv) −x+1, −y+1, −z+1; (v) x, −y+1/2, z−1/2; (vi) −x+2, y+1/2, −z+1/2; (vii) −x+2, −y+1, −z+1; (viii) −x+2, −y, −z+1; (ix) −x+1, y−1/2, −z+1/2; (x) x, −y+1/2, z+1/2; (xi) x+1, y, z; (xii) −x+2, y−1/2, −z+1/2. |