Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804032416/rz6030sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804032416/rz6030Isup2.hkl |
CCDC reference: 262256
Key indicators
- Single-crystal X-ray study
- T = 133 K
- Mean (C-C) = 0.003 Å
- R factor = 0.025
- wR factor = 0.062
- Data-to-parameter ratio = 26.1
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Br - Cu .. 23.32 su
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.609 0.703 Tmin and Tmax expected: 0.421 0.562 RR = 1.156 Please check that your absorption correction is appropriate. PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.17 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.80 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H24 .. BR .. 3.15 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H15 .. BR .. 3.13 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H25 .. BR .. 2.94 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.799 Tmax scaled 0.562 Tmin scaled 0.487
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.
[CuBr(C7H9N)2] | F(000) = 720 |
Mr = 357.75 | Dx = 1.591 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5168 (6) Å | Cell parameters from 5859 reflections |
b = 15.124 (1) Å | θ = 2–30.5° |
c = 13.1804 (10) Å | µ = 4.12 mm−1 |
β = 94.610 (4)° | T = 133 K |
V = 1493.55 (19) Å3 | Prism, colourless |
Z = 4 | 0.33 × 0.18 × 0.14 mm |
Bruker SMART 1000 CCD diffractometer | 4367 independent reflections |
Radiation source: fine-focus sealed tube | 3613 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
Detector resolution: 8.192 pixels mm-1 | θmax = 30.0°, θmin = 2.1° |
ω and φ scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | k = −21→20 |
Tmin = 0.609, Tmax = 0.703 | l = −18→18 |
30827 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)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.062 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0266P)2 + 0.8705P] where P = (Fo2 + 2Fc2)/3 |
4367 reflections | (Δ/σ)max = 0.001 |
167 parameters | Δρmax = 0.52 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 1.8528 (0.0051) x + 14.2565 (0.0038) y + 3.2184 (0.0090) z = 6.0063 (0.0053) * -0.0023 (0.0011) N11 * 0.0068 (0.0011) C12 * -0.0037 (0.0012) C13 * -0.0034 (0.0013) C14 * 0.0079 (0.0013) C15 * -0.0052 (0.0012) C16 Rms deviation of fitted atoms = 0.0053 5.0828 (0.0021) x + 8.1276 (0.0050) y - 7.3372 (0.0066) z = 1.1191 (0.0075) Angle to previous plane (with approximate e.s.d.) = 76.91 (0.04) * 0.0004 (0.0005) Cu * -0.0001 (0.0002) Br * -0.0002 (0.0002) N11 * -0.0002 (0.0002) N21 Rms deviation of fitted atoms = 0.0003 7.1265 (0.0019) x - 2.8894 (0.0111) y + 2.3362 (0.0095) z = 6.3076 (0.0098) Angle to previous plane (with approximate e.s.d.) = 65.78 (0.04) * 0.0046 (0.0011) N21 * 0.0002 (0.0012) C22 * -0.0048 (0.0012) C23 * 0.0048 (0.0013) C24 * 0.0000 (0.0013) C25 * -0.0048 (0.0013) C26 Rms deviation of fitted atoms = 0.0039 |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Cu | 0.78705 (3) | 0.345359 (15) | 0.775201 (16) | 0.02675 (6) | |
Br | 0.99775 (3) | 0.231286 (13) | 0.794882 (14) | 0.02960 (6) | |
N11 | 0.6053 (2) | 0.35164 (9) | 0.65630 (11) | 0.0218 (3) | |
C12 | 0.6404 (2) | 0.37813 (11) | 0.56203 (13) | 0.0213 (3) | |
C13 | 0.5084 (3) | 0.37856 (12) | 0.48081 (13) | 0.0258 (4) | |
C14 | 0.3376 (3) | 0.35220 (12) | 0.49940 (16) | 0.0315 (4) | |
H14 | 0.2456 | 0.3519 | 0.4456 | 0.038* | |
C15 | 0.3008 (3) | 0.32628 (12) | 0.59654 (17) | 0.0323 (4) | |
H15 | 0.1837 | 0.3091 | 0.6105 | 0.039* | |
C16 | 0.4375 (3) | 0.32614 (12) | 0.67178 (15) | 0.0273 (4) | |
H16 | 0.4131 | 0.3072 | 0.7380 | 0.033* | |
C17 | 0.8276 (3) | 0.40667 (13) | 0.54811 (15) | 0.0308 (4) | |
H17A | 0.9011 | 0.3998 | 0.6125 | 0.037* | |
H17B | 0.8277 | 0.4688 | 0.5270 | 0.037* | |
H17C | 0.8765 | 0.3701 | 0.4957 | 0.037* | |
C18 | 0.5528 (3) | 0.40572 (15) | 0.37565 (14) | 0.0389 (5) | |
H18A | 0.4464 | 0.3997 | 0.3281 | 0.047* | |
H18B | 0.6480 | 0.3677 | 0.3536 | 0.047* | |
H18C | 0.5928 | 0.4674 | 0.3770 | 0.047* | |
N21 | 0.77782 (19) | 0.44271 (9) | 0.87673 (10) | 0.0215 (3) | |
C22 | 0.7404 (2) | 0.43087 (11) | 0.97448 (13) | 0.0218 (3) | |
C23 | 0.7454 (2) | 0.50110 (12) | 1.04366 (13) | 0.0240 (3) | |
C24 | 0.7914 (3) | 0.58437 (12) | 1.01048 (15) | 0.0296 (4) | |
H24 | 0.7975 | 0.6330 | 1.0563 | 0.035* | |
C25 | 0.8286 (3) | 0.59627 (12) | 0.90987 (16) | 0.0308 (4) | |
H25 | 0.8595 | 0.6530 | 0.8858 | 0.037* | |
C26 | 0.8198 (2) | 0.52466 (12) | 0.84607 (14) | 0.0259 (4) | |
H26 | 0.8443 | 0.5331 | 0.7771 | 0.031* | |
C27 | 0.6959 (3) | 0.33871 (12) | 1.00552 (15) | 0.0323 (4) | |
H27A | 0.7144 | 0.2978 | 0.9496 | 0.039* | |
H27B | 0.5709 | 0.3362 | 1.0215 | 0.039* | |
H27C | 0.7733 | 0.3218 | 1.0658 | 0.039* | |
C28 | 0.7046 (3) | 0.48584 (15) | 1.15236 (15) | 0.0376 (5) | |
H28A | 0.7249 | 0.5406 | 1.1913 | 0.045* | |
H28B | 0.7827 | 0.4393 | 1.1824 | 0.045* | |
H28C | 0.5798 | 0.4677 | 1.1541 | 0.045* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu | 0.03061 (13) | 0.02861 (12) | 0.02073 (11) | 0.00035 (9) | 0.00018 (8) | −0.00083 (8) |
Br | 0.03186 (11) | 0.03167 (10) | 0.02504 (9) | 0.00735 (7) | 0.00095 (7) | −0.00020 (7) |
N11 | 0.0243 (8) | 0.0199 (6) | 0.0212 (7) | 0.0041 (5) | 0.0017 (5) | −0.0011 (5) |
C12 | 0.0221 (9) | 0.0193 (7) | 0.0226 (8) | 0.0049 (6) | 0.0018 (6) | −0.0017 (6) |
C13 | 0.0302 (10) | 0.0237 (8) | 0.0230 (8) | 0.0082 (7) | −0.0018 (7) | −0.0025 (6) |
C14 | 0.0280 (10) | 0.0261 (9) | 0.0382 (10) | 0.0055 (7) | −0.0109 (8) | −0.0065 (8) |
C15 | 0.0219 (9) | 0.0244 (9) | 0.0504 (12) | −0.0001 (7) | 0.0023 (8) | −0.0006 (8) |
C16 | 0.0285 (10) | 0.0226 (8) | 0.0317 (9) | 0.0031 (7) | 0.0089 (7) | 0.0013 (7) |
C17 | 0.0254 (10) | 0.0355 (10) | 0.0322 (9) | 0.0016 (7) | 0.0056 (7) | 0.0037 (8) |
C18 | 0.0490 (13) | 0.0463 (12) | 0.0209 (8) | 0.0171 (10) | −0.0001 (8) | 0.0018 (8) |
N21 | 0.0205 (7) | 0.0237 (7) | 0.0202 (6) | 0.0023 (5) | −0.0002 (5) | 0.0014 (5) |
C22 | 0.0193 (8) | 0.0226 (8) | 0.0235 (8) | 0.0020 (6) | 0.0019 (6) | 0.0036 (6) |
C23 | 0.0209 (9) | 0.0298 (9) | 0.0213 (8) | 0.0053 (6) | 0.0016 (6) | −0.0012 (6) |
C24 | 0.0268 (10) | 0.0255 (9) | 0.0360 (10) | 0.0032 (7) | 0.0002 (7) | −0.0067 (7) |
C25 | 0.0292 (10) | 0.0212 (8) | 0.0424 (11) | 0.0001 (7) | 0.0053 (8) | 0.0045 (7) |
C26 | 0.0255 (9) | 0.0275 (9) | 0.0247 (8) | 0.0031 (7) | 0.0035 (7) | 0.0084 (7) |
C27 | 0.0398 (11) | 0.0252 (9) | 0.0331 (10) | −0.0030 (7) | 0.0100 (8) | 0.0041 (7) |
C28 | 0.0425 (12) | 0.0470 (12) | 0.0245 (9) | 0.0108 (9) | 0.0095 (8) | −0.0014 (8) |
Cu—N21 | 1.9946 (14) | C18—H18C | 0.9800 |
Cu—N11 | 1.9970 (15) | N21—C26 | 1.349 (2) |
Cu—Br | 2.3422 (3) | N21—C22 | 1.353 (2) |
N11—C16 | 1.350 (2) | C22—C23 | 1.398 (2) |
N11—C12 | 1.352 (2) | C22—C27 | 1.498 (2) |
C12—C13 | 1.400 (2) | C23—C24 | 1.386 (3) |
C12—C17 | 1.497 (3) | C23—C28 | 1.507 (2) |
C13—C14 | 1.384 (3) | C24—C25 | 1.389 (3) |
C13—C18 | 1.509 (3) | C24—H24 | 0.9500 |
C14—C15 | 1.388 (3) | C25—C26 | 1.369 (3) |
C14—H14 | 0.9500 | C25—H25 | 0.9500 |
C15—C16 | 1.369 (3) | C26—H26 | 0.9500 |
C15—H15 | 0.9500 | C27—H27A | 0.9800 |
C16—H16 | 0.9500 | C27—H27B | 0.9800 |
C17—H17A | 0.9800 | C27—H27C | 0.9800 |
C17—H17B | 0.9800 | C28—H28A | 0.9800 |
C17—H17C | 0.9800 | C28—H28B | 0.9800 |
C18—H18A | 0.9800 | C28—H28C | 0.9800 |
C18—H18B | 0.9800 | ||
N21—Cu—N11 | 115.65 (6) | H18B—C18—H18C | 109.5 |
N21—Cu—Br | 121.95 (4) | C26—N21—C22 | 118.59 (15) |
N11—Cu—Br | 122.41 (4) | C26—N21—Cu | 117.11 (12) |
C16—N11—C12 | 118.54 (15) | C22—N21—Cu | 124.22 (12) |
C16—N11—Cu | 117.16 (12) | N21—C22—C23 | 121.57 (15) |
C12—N11—Cu | 124.29 (12) | N21—C22—C27 | 116.84 (15) |
N11—C12—C13 | 121.67 (16) | C23—C22—C27 | 121.58 (16) |
N11—C12—C17 | 116.96 (15) | C24—C23—C22 | 118.61 (16) |
C13—C12—C17 | 121.37 (16) | C24—C23—C28 | 120.94 (17) |
C14—C13—C12 | 118.28 (17) | C22—C23—C28 | 120.44 (17) |
C14—C13—C18 | 121.19 (17) | C23—C24—C25 | 119.57 (17) |
C12—C13—C18 | 120.52 (18) | C23—C24—H24 | 120.2 |
C13—C14—C15 | 120.07 (17) | C25—C24—H24 | 120.2 |
C13—C14—H14 | 120.0 | C26—C25—C24 | 118.71 (17) |
C15—C14—H14 | 120.0 | C26—C25—H25 | 120.6 |
C16—C15—C14 | 118.35 (18) | C24—C25—H25 | 120.6 |
C16—C15—H15 | 120.8 | N21—C26—C25 | 122.93 (16) |
C14—C15—H15 | 120.8 | N21—C26—H26 | 118.5 |
N11—C16—C15 | 123.08 (17) | C25—C26—H26 | 118.5 |
N11—C16—H16 | 118.5 | C22—C27—H27A | 109.5 |
C15—C16—H16 | 118.5 | C22—C27—H27B | 109.5 |
C12—C17—H17A | 109.5 | H27A—C27—H27B | 109.5 |
C12—C17—H17B | 109.5 | C22—C27—H27C | 109.5 |
H17A—C17—H17B | 109.5 | H27A—C27—H27C | 109.5 |
C12—C17—H17C | 109.5 | H27B—C27—H27C | 109.5 |
H17A—C17—H17C | 109.5 | C23—C28—H28A | 109.5 |
H17B—C17—H17C | 109.5 | C23—C28—H28B | 109.5 |
C13—C18—H18A | 109.5 | H28A—C28—H28B | 109.5 |
C13—C18—H18B | 109.5 | C23—C28—H28C | 109.5 |
H18A—C18—H18B | 109.5 | H28A—C28—H28C | 109.5 |
C13—C18—H18C | 109.5 | H28B—C28—H28C | 109.5 |
H18A—C18—H18C | 109.5 | ||
N21—Cu—N11—C16 | −77.66 (13) | N11—Cu—N21—C26 | −66.94 (14) |
Br—Cu—N11—C16 | 102.28 (12) | Br—Cu—N21—C26 | 113.12 (12) |
N21—Cu—N11—C12 | 103.51 (13) | N11—Cu—N21—C22 | 116.16 (14) |
Br—Cu—N11—C12 | −76.55 (14) | Br—Cu—N21—C22 | −63.79 (15) |
C16—N11—C12—C13 | −0.8 (2) | C26—N21—C22—C23 | −0.4 (2) |
Cu—N11—C12—C13 | 178.00 (12) | Cu—N21—C22—C23 | 176.43 (12) |
C16—N11—C12—C17 | 179.47 (15) | C26—N21—C22—C27 | −179.52 (16) |
Cu—N11—C12—C17 | −1.7 (2) | Cu—N21—C22—C27 | −2.7 (2) |
N11—C12—C13—C14 | 1.0 (2) | N21—C22—C23—C24 | −0.5 (3) |
C17—C12—C13—C14 | −179.33 (16) | C27—C22—C23—C24 | 178.58 (18) |
N11—C12—C13—C18 | −178.05 (16) | N21—C22—C23—C28 | −179.47 (17) |
C17—C12—C13—C18 | 1.7 (3) | C27—C22—C23—C28 | −0.4 (3) |
C12—C13—C14—C15 | 0.0 (3) | C22—C23—C24—C25 | 0.9 (3) |
C18—C13—C14—C15 | 179.04 (18) | C28—C23—C24—C25 | 179.89 (18) |
C13—C14—C15—C16 | −1.1 (3) | C23—C24—C25—C26 | −0.4 (3) |
C12—N11—C16—C15 | −0.4 (3) | C22—N21—C26—C25 | 0.9 (3) |
Cu—N11—C16—C15 | −179.26 (14) | Cu—N21—C26—C25 | −176.16 (14) |
C14—C15—C16—N11 | 1.3 (3) | C24—C25—C26—N21 | −0.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···Bri | 0.95 | 2.90 | 3.7791 (19) | 155 |
C24—H24···Brii | 0.95 | 3.15 | 4.0264 (19) | 154 |
C15—H15···Briii | 0.95 | 3.13 | 3.879 (2) | 137 |
C25—H25···Briv | 0.95 | 2.94 | 3.7045 (19) | 139 |
Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) −x+2, −y+1, −z+2; (iii) x−1, y, z; (iv) −x+2, y+1/2, −z+3/2. |