Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the title compound, [CuBr(C16H14Cl2N2)(C18H15P)], the coordination polyhedron around the CuI centre is approximately tetra­hedral, distorted by the restricted bite angle of the chelating ligand. Intra- and inter­molecular C—H...π and π–π stacking inter­actions are observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048239/bi2099sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048239/bi2099Isup2.hkl
Contains datablock I

CCDC reference: 629445

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.033
  • wR factor = 0.076
  • Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Br - Cu .. 9.14 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP III (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.

Bromo bis[N,N'-(2-chlorobenzylidene)ethylenediamine(triphenylphosphine)]copper(I) top
Crystal data top
[CuBr(C16H14Cl2N2)(C18H15P)]F(000) = 1440
Mr = 710.91Dx = 1.544 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6534 reflections
a = 10.3050 (5) Åθ = 2.2–27.9°
b = 21.671 (1) ŵ = 2.28 mm1
c = 14.0214 (7) ÅT = 173 K
β = 102.463 (1)°Block, pale blue
V = 3057.6 (3) Å30.32 × 0.24 × 0.22 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
6634 independent reflections
Radiation source: fine-focus sealed tube4939 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
φ and ω scansθmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)
h = 1310
Tmin = 0.479, Tmax = 0.601k = 2727
18624 measured reflectionsl = 1417
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0362P)2]
where P = (Fo2 + 2Fc2)/3
6634 reflections(Δ/σ)max < 0.001
370 parametersΔρmax = 0.70 e Å3
0 restraintsΔρmin = 0.36 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.

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
Br0.92465 (3)0.213261 (13)0.26311 (2)0.02797 (8)
Cu0.70949 (3)0.157059 (14)0.22960 (2)0.02159 (9)
P0.64647 (6)0.09115 (3)0.33018 (5)0.01932 (14)
Cl10.29271 (8)0.31235 (4)0.31605 (7)0.0468 (2)
Cl20.63752 (9)0.03380 (4)0.05972 (6)0.0504 (2)
N10.6577 (2)0.13903 (10)0.07872 (15)0.0229 (5)
N20.5909 (2)0.23711 (10)0.19021 (15)0.0245 (5)
C10.5513 (3)0.18280 (12)0.0350 (2)0.0303 (6)
H1A0.46600.16730.04300.036*
H1B0.54800.18710.03440.036*
C20.5790 (3)0.24477 (12)0.08462 (19)0.0294 (6)
H2A0.66080.26180.07210.035*
H2B0.50730.27320.05880.035*
C30.5347 (3)0.27632 (13)0.2354 (2)0.0311 (7)
H30.48120.30640.19940.037*
C40.5508 (3)0.27606 (12)0.3431 (2)0.0282 (6)
C50.4471 (3)0.29219 (12)0.3878 (2)0.0304 (6)
C60.4611 (3)0.29158 (13)0.4879 (2)0.0378 (7)
H60.39000.30210.51570.045*
C70.5818 (3)0.27518 (14)0.5461 (2)0.0391 (8)
H70.59220.27440.61360.047*
C80.6874 (3)0.25995 (14)0.5043 (2)0.0367 (7)
H80.76880.24930.54380.044*
C90.6722 (3)0.26054 (13)0.4037 (2)0.0307 (6)
H90.74390.25050.37620.037*
C100.6832 (3)0.09578 (12)0.02426 (19)0.0291 (6)
H100.63190.09250.03880.035*
C110.7905 (3)0.05068 (12)0.05674 (18)0.0266 (6)
C120.9070 (3)0.06782 (13)0.12243 (19)0.0288 (6)
H120.91630.10800.14620.035*
C131.0087 (3)0.02577 (14)0.1526 (2)0.0341 (7)
H131.08670.03790.19540.041*
C140.9939 (3)0.03432 (14)0.1189 (2)0.0409 (8)
H141.06140.06280.14040.049*
C150.8808 (3)0.05251 (14)0.0543 (2)0.0386 (8)
H150.87140.09300.03200.046*
C160.7807 (3)0.00993 (13)0.02254 (19)0.0320 (7)
C170.5968 (3)0.01218 (12)0.28885 (17)0.0221 (6)
C180.4829 (3)0.01602 (13)0.30571 (19)0.0294 (6)
H180.42420.00640.33410.035*
C190.4559 (3)0.07734 (14)0.2805 (2)0.0352 (7)
H190.37880.09570.29150.042*
C200.5433 (3)0.11115 (13)0.2392 (2)0.0381 (8)
H200.52580.15240.22340.046*
C210.6563 (3)0.08376 (13)0.2215 (2)0.0370 (7)
H210.71500.10640.19340.044*
C220.6823 (3)0.02199 (12)0.24584 (19)0.0285 (6)
H220.75810.00340.23300.034*
C230.7657 (2)0.07320 (11)0.44385 (17)0.0197 (5)
C240.8871 (3)0.10405 (12)0.46455 (18)0.0250 (6)
H240.90460.13500.42320.030*
C250.9819 (3)0.08835 (13)0.54725 (19)0.0311 (7)
H251.06300.10890.56090.037*
C260.9576 (3)0.04291 (13)0.6090 (2)0.0331 (7)
H261.02170.03300.66440.040*
C270.8372 (3)0.01175 (13)0.5889 (2)0.0335 (7)
H270.82020.01890.63100.040*
C280.7425 (3)0.02640 (12)0.50636 (19)0.0284 (6)
H280.66260.00490.49230.034*
C290.4961 (2)0.11774 (11)0.36652 (18)0.0206 (5)
C300.3872 (3)0.13199 (12)0.29103 (19)0.0250 (6)
H300.39590.12970.22650.030*
C310.2671 (3)0.14942 (12)0.3112 (2)0.0275 (6)
H310.19510.15780.26030.033*
C320.2537 (3)0.15444 (13)0.4070 (2)0.0322 (7)
H320.17300.16650.42060.039*
C330.3603 (3)0.14151 (13)0.4819 (2)0.0333 (7)
H330.35140.14490.54630.040*
C340.4815 (3)0.12330 (12)0.46207 (19)0.0270 (6)
H340.55310.11480.51330.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.02565 (15)0.02756 (15)0.03214 (15)0.00324 (12)0.00941 (11)0.00043 (12)
Cu0.02398 (17)0.02203 (17)0.01900 (16)0.00192 (13)0.00518 (13)0.00394 (13)
P0.0199 (3)0.0205 (3)0.0169 (3)0.0000 (3)0.0025 (3)0.0024 (3)
Cl10.0334 (4)0.0431 (5)0.0629 (5)0.0127 (4)0.0083 (4)0.0032 (4)
Cl20.0637 (6)0.0394 (5)0.0422 (5)0.0039 (4)0.0012 (4)0.0137 (4)
N10.0266 (12)0.0231 (12)0.0189 (11)0.0026 (9)0.0046 (9)0.0027 (9)
N20.0279 (13)0.0206 (11)0.0248 (12)0.0022 (10)0.0053 (10)0.0022 (9)
C10.0324 (16)0.0314 (15)0.0247 (15)0.0055 (13)0.0010 (12)0.0025 (12)
C20.0340 (16)0.0245 (15)0.0285 (15)0.0066 (12)0.0044 (12)0.0093 (12)
C30.0310 (16)0.0258 (16)0.0361 (16)0.0039 (12)0.0067 (13)0.0030 (12)
C40.0306 (15)0.0214 (15)0.0337 (16)0.0001 (12)0.0095 (12)0.0032 (11)
C50.0307 (16)0.0197 (14)0.0414 (17)0.0007 (12)0.0095 (13)0.0049 (12)
C60.0389 (18)0.0303 (16)0.0499 (19)0.0024 (14)0.0219 (15)0.0086 (14)
C70.047 (2)0.0413 (19)0.0323 (17)0.0075 (15)0.0152 (15)0.0115 (13)
C80.0321 (17)0.0420 (18)0.0344 (17)0.0038 (14)0.0037 (13)0.0065 (14)
C90.0259 (15)0.0321 (16)0.0352 (16)0.0000 (12)0.0089 (12)0.0077 (13)
C100.0356 (16)0.0291 (15)0.0208 (14)0.0028 (13)0.0021 (12)0.0028 (12)
C110.0356 (16)0.0279 (15)0.0182 (13)0.0021 (12)0.0099 (12)0.0019 (11)
C120.0366 (16)0.0293 (15)0.0228 (14)0.0008 (13)0.0112 (12)0.0022 (11)
C130.0378 (17)0.0409 (18)0.0251 (15)0.0059 (14)0.0103 (13)0.0054 (13)
C140.052 (2)0.0389 (19)0.0345 (17)0.0153 (16)0.0159 (15)0.0078 (14)
C150.061 (2)0.0262 (16)0.0333 (17)0.0080 (15)0.0210 (16)0.0005 (13)
C160.0453 (18)0.0332 (16)0.0207 (14)0.0032 (14)0.0144 (13)0.0004 (12)
C170.0255 (14)0.0244 (14)0.0141 (12)0.0012 (11)0.0011 (10)0.0024 (10)
C180.0309 (16)0.0314 (16)0.0249 (14)0.0038 (12)0.0036 (12)0.0012 (12)
C190.0409 (18)0.0355 (17)0.0267 (15)0.0150 (14)0.0014 (13)0.0006 (13)
C200.065 (2)0.0202 (15)0.0243 (15)0.0051 (15)0.0000 (15)0.0008 (12)
C210.053 (2)0.0283 (16)0.0300 (16)0.0061 (15)0.0098 (14)0.0045 (12)
C220.0323 (16)0.0305 (16)0.0229 (14)0.0012 (12)0.0064 (12)0.0024 (11)
C230.0205 (13)0.0204 (13)0.0173 (12)0.0021 (10)0.0022 (10)0.0013 (10)
C240.0273 (14)0.0239 (14)0.0227 (14)0.0013 (11)0.0027 (11)0.0032 (11)
C250.0252 (15)0.0365 (17)0.0279 (15)0.0058 (13)0.0026 (12)0.0003 (12)
C260.0325 (16)0.0385 (17)0.0239 (15)0.0035 (13)0.0034 (12)0.0049 (13)
C270.0400 (18)0.0326 (16)0.0255 (15)0.0040 (14)0.0023 (13)0.0128 (12)
C280.0251 (15)0.0317 (16)0.0265 (14)0.0034 (12)0.0012 (12)0.0057 (12)
C290.0216 (13)0.0180 (13)0.0217 (13)0.0015 (10)0.0035 (10)0.0014 (10)
C300.0255 (14)0.0266 (14)0.0217 (13)0.0003 (11)0.0022 (11)0.0001 (11)
C310.0216 (14)0.0255 (15)0.0330 (15)0.0015 (11)0.0006 (11)0.0028 (12)
C320.0247 (15)0.0316 (16)0.0422 (17)0.0022 (12)0.0112 (13)0.0021 (13)
C330.0369 (17)0.0386 (17)0.0271 (15)0.0035 (14)0.0127 (13)0.0004 (13)
C340.0284 (15)0.0267 (15)0.0245 (14)0.0038 (12)0.0024 (11)0.0021 (11)
Geometric parameters (Å, º) top
Cu—Br2.4841 (4)C14—C151.371 (4)
Cu—N12.104 (2)C14—H140.930
Cu—N22.126 (2)C15—C161.384 (4)
Cu—P2.2014 (7)C15—H150.930
N1—C11.479 (3)C17—C221.385 (4)
N1—C101.272 (3)C17—C181.388 (4)
N2—C21.469 (3)C18—C191.388 (4)
N2—C31.272 (3)C18—H180.930
P—C291.826 (3)C19—C201.382 (4)
P—C231.832 (2)C19—H190.930
P—C171.844 (3)C20—C211.376 (4)
Cl1—C51.744 (3)C20—H200.930
Cl2—C161.744 (3)C21—C221.393 (4)
C1—C21.512 (4)C21—H210.930
C1—H1A0.970C22—H220.930
C1—H1B0.970C23—C241.393 (3)
C2—H2A0.970C23—C281.394 (3)
C2—H2B0.970C24—C251.388 (3)
C3—C41.483 (4)C24—H240.930
C3—H30.930C25—C261.370 (4)
C4—C91.393 (4)C25—H250.930
C4—C51.394 (4)C26—C271.387 (4)
C5—C61.380 (4)C26—H260.930
C6—C71.379 (4)C27—C281.380 (3)
C6—H60.930C27—H270.930
C7—C81.383 (4)C28—H280.930
C7—H70.930C29—C341.385 (4)
C8—C91.385 (4)C29—C301.401 (3)
C8—H80.930C30—C311.380 (4)
C9—H90.930C30—H300.930
C10—C111.472 (4)C31—C321.383 (4)
C10—H100.930C31—H310.930
C11—C161.395 (4)C32—C331.375 (4)
C11—C121.396 (4)C32—H320.930
C12—C131.385 (4)C33—C341.395 (4)
C12—H120.930C33—H330.930
C13—C141.382 (4)C34—H340.930
C13—H130.930
N1—Cu—N283.31 (8)C15—C14—C13120.9 (3)
N1—Cu—P118.54 (6)C15—C14—H14119.6
N2—Cu—P117.61 (7)C13—C14—H14119.6
N1—Cu—Br107.68 (6)C14—C15—C16119.3 (3)
N2—Cu—Br95.09 (6)C14—C15—H15120.4
P—Cu—Br124.86 (2)C16—C15—H15120.4
Cu—N1—C10134.4 (2)C15—C16—C11121.6 (3)
Cu—N1—C1107.6 (2)C15—C16—Cl2118.7 (2)
Cu—N2—C3135.6 (2)C11—C16—Cl2119.7 (2)
Cu—N2—C2105.8 (2)C22—C17—C18118.7 (2)
C29—P—C23105.9 (1)C22—C17—P118.3 (2)
C29—P—C17100.7 (1)C18—C17—P122.9 (2)
C23—P—C1799.5 (1)C19—C18—C17120.6 (3)
C29—P—Cu111.07 (8)C19—C18—H18119.7
C23—P—Cu117.38 (9)C17—C18—H18119.7
C17—P—Cu120.09 (9)C20—C19—C18120.1 (3)
C10—N1—C1117.0 (2)C20—C19—H19120.0
C3—N2—C2118.6 (2)C18—C19—H19120.0
N1—C1—C2109.2 (2)C21—C20—C19120.0 (3)
N1—C1—H1A109.8C21—C20—H20120.0
C2—C1—H1A109.8C19—C20—H20120.0
N1—C1—H1B109.8C20—C21—C22119.7 (3)
C2—C1—H1B109.8C20—C21—H21120.1
H1A—C1—H1B108.3C22—C21—H21120.1
N2—C2—C1109.3 (2)C17—C22—C21120.9 (3)
N2—C2—H2A109.8C17—C22—H22119.6
C1—C2—H2A109.8C21—C22—H22119.6
N2—C2—H2B109.8C24—C23—C28119.1 (2)
C1—C2—H2B109.8C24—C23—P118.89 (19)
H2A—C2—H2B108.3C28—C23—P121.83 (19)
N2—C3—C4122.8 (2)C25—C24—C23119.7 (2)
N2—C3—H3118.6C25—C24—H24120.2
C4—C3—H3118.6C23—C24—H24120.2
C9—C4—C5117.5 (3)C26—C25—C24120.8 (3)
C9—C4—C3120.7 (3)C26—C25—H25119.6
C5—C4—C3121.9 (3)C24—C25—H25119.6
C6—C5—C4122.2 (3)C25—C26—C27120.0 (2)
C6—C5—Cl1118.1 (2)C25—C26—H26120.0
C4—C5—Cl1119.7 (2)C27—C26—H26120.0
C7—C6—C5119.2 (3)C28—C27—C26119.8 (3)
C7—C6—H6120.4C28—C27—H27120.1
C5—C6—H6120.4C26—C27—H27120.1
C6—C7—C8120.1 (3)C27—C28—C23120.6 (3)
C6—C7—H7119.9C27—C28—H28119.7
C8—C7—H7119.9C23—C28—H28119.7
C7—C8—C9120.2 (3)C34—C29—C30118.4 (2)
C7—C8—H8119.9C34—C29—P124.95 (19)
C9—C8—H8119.9C30—C29—P116.6 (2)
C8—C9—C4120.8 (3)C31—C30—C29120.8 (3)
C8—C9—H9119.6C31—C30—H30119.6
C4—C9—H9119.6C29—C30—H30119.6
N1—C10—C11122.8 (2)C30—C31—C32120.2 (2)
N1—C10—H10118.6C30—C31—H31119.9
C11—C10—H10118.6C32—C31—H31119.9
C16—C11—C12117.8 (3)C33—C32—C31119.7 (3)
C16—C11—C10121.7 (2)C33—C32—H32120.2
C12—C11—C10120.6 (2)C31—C32—H32120.2
C13—C12—C11120.9 (3)C32—C33—C34120.5 (3)
C13—C12—H12119.6C32—C33—H33119.8
C11—C12—H12119.6C34—C33—H33119.8
C14—C13—C12119.6 (3)C29—C34—C33120.4 (2)
C14—C13—H13120.2C29—C34—H34119.8
C12—C13—H13120.2C33—C34—H34119.8
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds