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The title compound, [CuBr(C7H9N)2], consists of monomeric molecules in which the Cu atom displays trigonal planar coordination, with Cu—N = 1.9970 (15) and 1.9946 (14) Å, and Cu—Br = 2.3422 (3) Å. The packing involves layer formation parallel to (10\bar{2}) by C—H...Br interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804032416/rz6030sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804032416/rz6030Isup2.hkl
Contains datablock I

CCDC reference: 262256

Key indicators

  • Single-crystal X-ray study
  • T = 133 K
  • Mean [sigma](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

Computing details top

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.

Bromobis(2,3-lutidine)copper(I) top
Crystal data top
[CuBr(C7H9N)2]F(000) = 720
Mr = 357.75Dx = 1.591 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.5168 (6) ÅCell parameters from 5859 reflections
b = 15.124 (1) Åθ = 2–30.5°
c = 13.1804 (10) ŵ = 4.12 mm1
β = 94.610 (4)°T = 133 K
V = 1493.55 (19) Å3Prism, colourless
Z = 40.33 × 0.18 × 0.14 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer
4367 independent reflections
Radiation source: fine-focus sealed tube3613 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
Detector resolution: 8.192 pixels mm-1θmax = 30.0°, θmin = 2.1°
ω and φ scansh = 1010
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
k = 2120
Tmin = 0.609, Tmax = 0.703l = 1818
30827 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062H-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 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = 0.29 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu0.78705 (3)0.345359 (15)0.775201 (16)0.02675 (6)
Br0.99775 (3)0.231286 (13)0.794882 (14)0.02960 (6)
N110.6053 (2)0.35164 (9)0.65630 (11)0.0218 (3)
C120.6404 (2)0.37813 (11)0.56203 (13)0.0213 (3)
C130.5084 (3)0.37856 (12)0.48081 (13)0.0258 (4)
C140.3376 (3)0.35220 (12)0.49940 (16)0.0315 (4)
H140.24560.35190.44560.038*
C150.3008 (3)0.32628 (12)0.59654 (17)0.0323 (4)
H150.18370.30910.61050.039*
C160.4375 (3)0.32614 (12)0.67178 (15)0.0273 (4)
H160.41310.30720.73800.033*
C170.8276 (3)0.40667 (13)0.54811 (15)0.0308 (4)
H17A0.90110.39980.61250.037*
H17B0.82770.46880.52700.037*
H17C0.87650.37010.49570.037*
C180.5528 (3)0.40572 (15)0.37565 (14)0.0389 (5)
H18A0.44640.39970.32810.047*
H18B0.64800.36770.35360.047*
H18C0.59280.46740.37700.047*
N210.77782 (19)0.44271 (9)0.87673 (10)0.0215 (3)
C220.7404 (2)0.43087 (11)0.97448 (13)0.0218 (3)
C230.7454 (2)0.50110 (12)1.04366 (13)0.0240 (3)
C240.7914 (3)0.58437 (12)1.01048 (15)0.0296 (4)
H240.79750.63301.05630.035*
C250.8286 (3)0.59627 (12)0.90987 (16)0.0308 (4)
H250.85950.65300.88580.037*
C260.8198 (2)0.52466 (12)0.84607 (14)0.0259 (4)
H260.84430.53310.77710.031*
C270.6959 (3)0.33871 (12)1.00552 (15)0.0323 (4)
H27A0.71440.29780.94960.039*
H27B0.57090.33621.02150.039*
H27C0.77330.32181.06580.039*
C280.7046 (3)0.48584 (15)1.15236 (15)0.0376 (5)
H28A0.72490.54061.19130.045*
H28B0.78270.43931.18240.045*
H28C0.57980.46771.15410.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.03061 (13)0.02861 (12)0.02073 (11)0.00035 (9)0.00018 (8)0.00083 (8)
Br0.03186 (11)0.03167 (10)0.02504 (9)0.00735 (7)0.00095 (7)0.00020 (7)
N110.0243 (8)0.0199 (6)0.0212 (7)0.0041 (5)0.0017 (5)0.0011 (5)
C120.0221 (9)0.0193 (7)0.0226 (8)0.0049 (6)0.0018 (6)0.0017 (6)
C130.0302 (10)0.0237 (8)0.0230 (8)0.0082 (7)0.0018 (7)0.0025 (6)
C140.0280 (10)0.0261 (9)0.0382 (10)0.0055 (7)0.0109 (8)0.0065 (8)
C150.0219 (9)0.0244 (9)0.0504 (12)0.0001 (7)0.0023 (8)0.0006 (8)
C160.0285 (10)0.0226 (8)0.0317 (9)0.0031 (7)0.0089 (7)0.0013 (7)
C170.0254 (10)0.0355 (10)0.0322 (9)0.0016 (7)0.0056 (7)0.0037 (8)
C180.0490 (13)0.0463 (12)0.0209 (8)0.0171 (10)0.0001 (8)0.0018 (8)
N210.0205 (7)0.0237 (7)0.0202 (6)0.0023 (5)0.0002 (5)0.0014 (5)
C220.0193 (8)0.0226 (8)0.0235 (8)0.0020 (6)0.0019 (6)0.0036 (6)
C230.0209 (9)0.0298 (9)0.0213 (8)0.0053 (6)0.0016 (6)0.0012 (6)
C240.0268 (10)0.0255 (9)0.0360 (10)0.0032 (7)0.0002 (7)0.0067 (7)
C250.0292 (10)0.0212 (8)0.0424 (11)0.0001 (7)0.0053 (8)0.0045 (7)
C260.0255 (9)0.0275 (9)0.0247 (8)0.0031 (7)0.0035 (7)0.0084 (7)
C270.0398 (11)0.0252 (9)0.0331 (10)0.0030 (7)0.0100 (8)0.0041 (7)
C280.0425 (12)0.0470 (12)0.0245 (9)0.0108 (9)0.0095 (8)0.0014 (8)
Geometric parameters (Å, º) top
Cu—N211.9946 (14)C18—H18C0.9800
Cu—N111.9970 (15)N21—C261.349 (2)
Cu—Br2.3422 (3)N21—C221.353 (2)
N11—C161.350 (2)C22—C231.398 (2)
N11—C121.352 (2)C22—C271.498 (2)
C12—C131.400 (2)C23—C241.386 (3)
C12—C171.497 (3)C23—C281.507 (2)
C13—C141.384 (3)C24—C251.389 (3)
C13—C181.509 (3)C24—H240.9500
C14—C151.388 (3)C25—C261.369 (3)
C14—H140.9500C25—H250.9500
C15—C161.369 (3)C26—H260.9500
C15—H150.9500C27—H27A0.9800
C16—H160.9500C27—H27B0.9800
C17—H17A0.9800C27—H27C0.9800
C17—H17B0.9800C28—H28A0.9800
C17—H17C0.9800C28—H28B0.9800
C18—H18A0.9800C28—H28C0.9800
C18—H18B0.9800
N21—Cu—N11115.65 (6)H18B—C18—H18C109.5
N21—Cu—Br121.95 (4)C26—N21—C22118.59 (15)
N11—Cu—Br122.41 (4)C26—N21—Cu117.11 (12)
C16—N11—C12118.54 (15)C22—N21—Cu124.22 (12)
C16—N11—Cu117.16 (12)N21—C22—C23121.57 (15)
C12—N11—Cu124.29 (12)N21—C22—C27116.84 (15)
N11—C12—C13121.67 (16)C23—C22—C27121.58 (16)
N11—C12—C17116.96 (15)C24—C23—C22118.61 (16)
C13—C12—C17121.37 (16)C24—C23—C28120.94 (17)
C14—C13—C12118.28 (17)C22—C23—C28120.44 (17)
C14—C13—C18121.19 (17)C23—C24—C25119.57 (17)
C12—C13—C18120.52 (18)C23—C24—H24120.2
C13—C14—C15120.07 (17)C25—C24—H24120.2
C13—C14—H14120.0C26—C25—C24118.71 (17)
C15—C14—H14120.0C26—C25—H25120.6
C16—C15—C14118.35 (18)C24—C25—H25120.6
C16—C15—H15120.8N21—C26—C25122.93 (16)
C14—C15—H15120.8N21—C26—H26118.5
N11—C16—C15123.08 (17)C25—C26—H26118.5
N11—C16—H16118.5C22—C27—H27A109.5
C15—C16—H16118.5C22—C27—H27B109.5
C12—C17—H17A109.5H27A—C27—H27B109.5
C12—C17—H17B109.5C22—C27—H27C109.5
H17A—C17—H17B109.5H27A—C27—H27C109.5
C12—C17—H17C109.5H27B—C27—H27C109.5
H17A—C17—H17C109.5C23—C28—H28A109.5
H17B—C17—H17C109.5C23—C28—H28B109.5
C13—C18—H18A109.5H28A—C28—H28B109.5
C13—C18—H18B109.5C23—C28—H28C109.5
H18A—C18—H18B109.5H28A—C28—H28C109.5
C13—C18—H18C109.5H28B—C28—H28C109.5
H18A—C18—H18C109.5
N21—Cu—N11—C1677.66 (13)N11—Cu—N21—C2666.94 (14)
Br—Cu—N11—C16102.28 (12)Br—Cu—N21—C26113.12 (12)
N21—Cu—N11—C12103.51 (13)N11—Cu—N21—C22116.16 (14)
Br—Cu—N11—C1276.55 (14)Br—Cu—N21—C2263.79 (15)
C16—N11—C12—C130.8 (2)C26—N21—C22—C230.4 (2)
Cu—N11—C12—C13178.00 (12)Cu—N21—C22—C23176.43 (12)
C16—N11—C12—C17179.47 (15)C26—N21—C22—C27179.52 (16)
Cu—N11—C12—C171.7 (2)Cu—N21—C22—C272.7 (2)
N11—C12—C13—C141.0 (2)N21—C22—C23—C240.5 (3)
C17—C12—C13—C14179.33 (16)C27—C22—C23—C24178.58 (18)
N11—C12—C13—C18178.05 (16)N21—C22—C23—C28179.47 (17)
C17—C12—C13—C181.7 (3)C27—C22—C23—C280.4 (3)
C12—C13—C14—C150.0 (3)C22—C23—C24—C250.9 (3)
C18—C13—C14—C15179.04 (18)C28—C23—C24—C25179.89 (18)
C13—C14—C15—C161.1 (3)C23—C24—C25—C260.4 (3)
C12—N11—C16—C150.4 (3)C22—N21—C26—C250.9 (3)
Cu—N11—C16—C15179.26 (14)Cu—N21—C26—C25176.16 (14)
C14—C15—C16—N111.3 (3)C24—C25—C26—N210.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···Bri0.952.903.7791 (19)155
C24—H24···Brii0.953.154.0264 (19)154
C15—H15···Briii0.953.133.879 (2)137
C25—H25···Briv0.952.943.7045 (19)139
Symmetry codes: (i) x1, y+1/2, z1/2; (ii) x+2, y+1, z+2; (iii) x1, y, z; (iv) x+2, y+1/2, z+3/2.
 

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