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The mol­ecular structure of the neutral title mononuclear complex, [CdCl2(C12H12N2O)2], is asymmetric, with the CdII atom located at the centre of a distorted tetra­hedron. The CdII atom is coordinated by two N atoms of two distinct monodentate 3-(1H-imidazol-1-yl)-1-phenyl­propan-1-one ligands and two Cl atoms. Inter­molecular C—H...Cl and C—H...O hydrogen bonds link the monomeric units to produce a one-dimensional supra­molecular chain in the [011] direction. These chains are further stabilized by intra-chain π–π stacking inter­actions between two neighbouring imidazole rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016042/zl2012sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016042/zl2012Isup2.hkl
Contains datablock I

CCDC reference: 647726

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.028
  • wR factor = 0.056
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.606 0.873 Tmin(prime) and Tmax expected: 0.708 0.873 RR(prime) = 0.856 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.85 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Dichloridobis[3-(1H-imidazol-1-yl)-1-phenylpropan-1-one-κN3]cadmium(II) top
Crystal data top
[CdCl2(C12H12N2O)2]F(000) = 1176
Mr = 583.77Dx = 1.580 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.2603 (13) ÅCell parameters from 4099 reflections
b = 9.2321 (13) Åθ = 2.3–23.6°
c = 28.902 (4) ŵ = 1.14 mm1
β = 96.798 (2)°T = 293 K
V = 2453.5 (6) Å3Prism, colourless
Z = 40.30 × 0.14 × 0.12 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
4318 independent reflections
Radiation source: fine-focus sealed tube3554 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 611
Tmin = 0.606, Tmax = 0.873k = 1010
12625 measured reflectionsl = 3434
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)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.056H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0176P)2 + 1.7709P]
where P = (Fo2 + 2Fc2)/3
4318 reflections(Δ/σ)max = 0.002
298 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.57 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
Cd11.19593 (2)0.04480 (2)0.235027 (7)0.04387 (7)
Cl11.32876 (8)0.12308 (9)0.19117 (3)0.0589 (2)
Cl21.23188 (9)0.00074 (9)0.31737 (2)0.0590 (2)
O10.5302 (3)0.3065 (2)0.05997 (7)0.0704 (6)
O21.0101 (2)0.7636 (2)0.07649 (7)0.0672 (6)
N10.9615 (2)0.0231 (3)0.20598 (7)0.0460 (6)
N20.7655 (2)0.0630 (2)0.16474 (7)0.0431 (5)
N31.2448 (2)0.2666 (2)0.21155 (7)0.0445 (6)
N41.2109 (2)0.4622 (2)0.16870 (7)0.0412 (5)
C10.9093 (3)0.0711 (3)0.17392 (10)0.0490 (7)
H10.96660.13570.15940.059*
C20.8424 (3)0.0949 (3)0.21762 (10)0.0517 (7)
H20.84430.16880.23950.062*
C30.7223 (3)0.0431 (3)0.19275 (10)0.0548 (8)
H30.62740.07380.19430.066*
C40.6723 (3)0.1514 (3)0.13124 (9)0.0524 (7)
H4A0.57250.14470.13820.063*
H4B0.70210.25200.13450.063*
C50.6797 (3)0.1038 (3)0.08177 (9)0.0431 (6)
H5A0.78070.09850.07610.052*
H5B0.63820.00760.07740.052*
C60.5993 (3)0.2058 (3)0.04705 (10)0.0463 (7)
C70.6088 (3)0.1816 (3)0.00360 (9)0.0424 (6)
C80.5513 (3)0.2865 (3)0.03523 (10)0.0515 (7)
H80.50760.36870.02450.062*
C90.5585 (3)0.2694 (4)0.08232 (11)0.0605 (8)
H90.51930.33970.10320.073*
C100.6236 (3)0.1489 (4)0.09839 (11)0.0612 (9)
H100.63000.13850.13010.073*
C110.6796 (3)0.0430 (4)0.06765 (11)0.0597 (8)
H110.72210.03930.07870.072*
C120.6726 (3)0.0594 (3)0.02039 (10)0.0509 (7)
H120.71090.01200.00020.061*
C131.1495 (3)0.3464 (3)0.18552 (9)0.0433 (7)
H131.05110.32450.17960.052*
C141.3750 (3)0.3371 (3)0.21145 (10)0.0490 (7)
H141.46320.30650.22710.059*
C151.3556 (3)0.4574 (3)0.18521 (10)0.0489 (7)
H151.42650.52420.17940.059*
C161.1353 (3)0.5734 (3)0.13892 (9)0.0447 (7)
H16A1.16340.66830.15130.054*
H16B1.03130.56300.13950.054*
C171.1690 (3)0.5639 (3)0.08910 (9)0.0434 (6)
H17A1.27250.57740.08830.052*
H17B1.14300.46850.07680.052*
C181.0866 (3)0.6770 (3)0.05922 (9)0.0419 (6)
C191.1020 (3)0.6840 (3)0.00838 (9)0.0386 (6)
C201.1847 (3)0.5856 (3)0.01339 (10)0.0478 (7)
H201.23010.50920.00360.057*
C211.2002 (3)0.6004 (4)0.06023 (10)0.0564 (8)
H211.25480.53340.07480.068*
C221.1346 (3)0.7141 (4)0.08518 (10)0.0570 (8)
H221.14750.72590.11640.068*
C231.0501 (3)0.8106 (3)0.06417 (10)0.0573 (8)
H231.00410.88620.08130.069*
C241.0336 (3)0.7953 (3)0.01777 (10)0.0501 (7)
H240.97570.86060.00380.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.04697 (12)0.04630 (13)0.03755 (11)0.00127 (11)0.00172 (8)0.00220 (10)
Cl10.0576 (5)0.0600 (5)0.0599 (5)0.0019 (4)0.0109 (4)0.0110 (4)
Cl20.0735 (5)0.0667 (5)0.0368 (4)0.0106 (4)0.0064 (4)0.0032 (3)
O10.0861 (17)0.0664 (15)0.0565 (13)0.0323 (13)0.0006 (12)0.0035 (12)
O20.0837 (16)0.0657 (15)0.0546 (13)0.0366 (13)0.0187 (12)0.0064 (11)
N10.0442 (13)0.0520 (15)0.0412 (13)0.0024 (12)0.0022 (11)0.0049 (11)
N20.0421 (13)0.0475 (15)0.0389 (12)0.0002 (11)0.0017 (10)0.0003 (11)
N30.0468 (14)0.0409 (14)0.0436 (13)0.0008 (11)0.0040 (11)0.0026 (11)
N40.0443 (13)0.0429 (13)0.0359 (11)0.0012 (11)0.0021 (10)0.0010 (11)
C10.0443 (17)0.0528 (19)0.0492 (17)0.0108 (14)0.0030 (13)0.0062 (14)
C20.0555 (19)0.0504 (18)0.0500 (17)0.0050 (15)0.0095 (15)0.0139 (14)
C30.0433 (17)0.064 (2)0.0578 (18)0.0097 (16)0.0100 (14)0.0045 (17)
C40.0519 (18)0.0562 (19)0.0473 (17)0.0101 (15)0.0015 (14)0.0002 (14)
C50.0375 (15)0.0459 (16)0.0449 (15)0.0016 (13)0.0003 (12)0.0001 (13)
C60.0383 (16)0.0470 (18)0.0520 (17)0.0026 (14)0.0010 (13)0.0010 (14)
C70.0324 (14)0.0467 (17)0.0466 (16)0.0037 (13)0.0006 (12)0.0018 (13)
C80.0466 (17)0.0502 (19)0.0565 (19)0.0027 (14)0.0007 (14)0.0029 (15)
C90.061 (2)0.069 (2)0.0503 (19)0.0077 (18)0.0023 (16)0.0171 (17)
C100.055 (2)0.081 (3)0.0478 (18)0.0141 (18)0.0086 (15)0.0001 (18)
C110.0527 (18)0.068 (2)0.0589 (19)0.0022 (17)0.0070 (15)0.0126 (18)
C120.0446 (16)0.0554 (19)0.0511 (17)0.0031 (15)0.0016 (13)0.0002 (15)
C130.0399 (15)0.0469 (17)0.0420 (15)0.0035 (13)0.0008 (12)0.0027 (13)
C140.0441 (17)0.0522 (19)0.0476 (17)0.0012 (14)0.0073 (13)0.0065 (14)
C150.0459 (17)0.0492 (18)0.0508 (16)0.0109 (15)0.0021 (13)0.0023 (15)
C160.0530 (17)0.0361 (16)0.0450 (15)0.0065 (13)0.0064 (13)0.0029 (12)
C170.0450 (15)0.0388 (16)0.0474 (15)0.0035 (13)0.0091 (12)0.0049 (13)
C180.0408 (15)0.0376 (16)0.0477 (16)0.0025 (13)0.0070 (13)0.0011 (13)
C190.0357 (14)0.0351 (15)0.0451 (15)0.0018 (12)0.0054 (12)0.0024 (12)
C200.0444 (16)0.0492 (18)0.0491 (16)0.0079 (13)0.0031 (13)0.0031 (13)
C210.0512 (18)0.070 (2)0.0489 (18)0.0042 (16)0.0088 (14)0.0099 (16)
C220.0528 (19)0.075 (2)0.0423 (16)0.0137 (17)0.0011 (14)0.0035 (16)
C230.063 (2)0.053 (2)0.0529 (19)0.0037 (16)0.0025 (16)0.0163 (15)
C240.0565 (18)0.0412 (17)0.0520 (17)0.0028 (14)0.0044 (14)0.0032 (14)
Geometric parameters (Å, º) top
Cd1—N32.220 (2)C8—H80.9300
Cd1—N12.242 (2)C9—C101.372 (4)
Cd1—Cl22.4008 (8)C9—H90.9300
Cd1—Cl12.4271 (8)C10—C111.380 (4)
O1—C61.213 (3)C10—H100.9300
O2—C181.214 (3)C11—C121.383 (4)
N1—C11.320 (3)C11—H110.9300
N1—C21.362 (3)C12—H120.9300
N2—C11.329 (3)C13—H130.9300
N2—C31.361 (4)C14—C151.345 (4)
N2—C41.467 (3)C14—H140.9300
N3—C131.315 (3)C15—H150.9300
N3—C141.371 (3)C16—C171.511 (4)
N4—C131.329 (3)C16—H16A0.9700
N4—C151.368 (3)C16—H16B0.9700
N4—C161.464 (3)C17—C181.503 (4)
C1—H10.9300C17—H17A0.9700
C2—C31.339 (4)C17—H17B0.9700
C2—H20.9300C18—C191.495 (4)
C3—H30.9300C19—C241.384 (4)
C4—C51.505 (4)C19—C201.386 (4)
C4—H4A0.9700C20—C211.385 (4)
C4—H4B0.9700C20—H200.9300
C5—C61.507 (4)C21—C221.374 (4)
C5—H5A0.9700C21—H210.9300
C5—H5B0.9700C22—C231.374 (4)
C6—C71.494 (4)C22—H220.9300
C7—C121.387 (4)C23—C241.375 (4)
C7—C81.394 (4)C23—H230.9300
C8—C91.379 (4)C24—H240.9300
N3—Cd1—N1101.04 (8)C9—C10—C11120.2 (3)
N3—Cd1—Cl2117.06 (6)C9—C10—H10119.9
N1—Cd1—Cl2111.71 (6)C11—C10—H10119.9
N3—Cd1—Cl1107.16 (6)C10—C11—C12120.0 (3)
N1—Cd1—Cl1105.99 (6)C10—C11—H11120.0
Cl2—Cd1—Cl1112.73 (3)C12—C11—H11120.0
C1—N1—C2104.7 (2)C11—C12—C7120.4 (3)
C1—N1—Cd1125.41 (18)C11—C12—H12119.8
C2—N1—Cd1129.79 (19)C7—C12—H12119.8
C1—N2—C3106.3 (2)N3—C13—N4111.9 (2)
C1—N2—C4126.7 (2)N3—C13—H13124.1
C3—N2—C4127.0 (2)N4—C13—H13124.1
C13—N3—C14105.3 (2)C15—C14—N3109.6 (3)
C13—N3—Cd1122.97 (18)C15—C14—H14125.2
C14—N3—Cd1130.55 (19)N3—C14—H14125.2
C13—N4—C15106.9 (2)C14—C15—N4106.4 (3)
C13—N4—C16125.7 (2)C14—C15—H15126.8
C15—N4—C16127.4 (2)N4—C15—H15126.8
N1—C1—N2112.2 (2)N4—C16—C17112.4 (2)
N1—C1—H1123.9N4—C16—H16A109.1
N2—C1—H1123.9C17—C16—H16A109.1
C3—C2—N1109.8 (3)N4—C16—H16B109.1
C3—C2—H2125.1C17—C16—H16B109.1
N1—C2—H2125.1H16A—C16—H16B107.9
C2—C3—N2107.0 (3)C18—C17—C16111.0 (2)
C2—C3—H3126.5C18—C17—H17A109.4
N2—C3—H3126.5C16—C17—H17A109.4
N2—C4—C5112.0 (2)C18—C17—H17B109.4
N2—C4—H4A109.2C16—C17—H17B109.4
C5—C4—H4A109.2H17A—C17—H17B108.0
N2—C4—H4B109.2O2—C18—C19120.3 (2)
C5—C4—H4B109.2O2—C18—C17120.2 (2)
H4A—C4—H4B107.9C19—C18—C17119.6 (2)
C4—C5—C6112.1 (2)C24—C19—C20118.7 (2)
C4—C5—H5A109.2C24—C19—C18118.6 (2)
C6—C5—H5A109.2C20—C19—C18122.7 (2)
C4—C5—H5B109.2C21—C20—C19120.4 (3)
C6—C5—H5B109.2C21—C20—H20119.8
H5A—C5—H5B107.9C19—C20—H20119.8
O1—C6—C7120.8 (3)C22—C21—C20119.9 (3)
O1—C6—C5120.7 (3)C22—C21—H21120.1
C7—C6—C5118.5 (2)C20—C21—H21120.1
C12—C7—C8118.8 (3)C23—C22—C21120.2 (3)
C12—C7—C6122.8 (3)C23—C22—H22119.9
C8—C7—C6118.4 (3)C21—C22—H22119.9
C9—C8—C7120.5 (3)C22—C23—C24120.0 (3)
C9—C8—H8119.7C22—C23—H23120.0
C7—C8—H8119.7C24—C23—H23120.0
C10—C9—C8120.1 (3)C23—C24—C19120.8 (3)
C10—C9—H9119.9C23—C24—H24119.6
C8—C9—H9119.9C19—C24—H24119.6
N3—Cd1—N1—C1116.2 (2)C7—C8—C9—C100.4 (4)
Cl2—Cd1—N1—C1118.6 (2)C8—C9—C10—C111.2 (5)
Cl1—Cd1—N1—C14.6 (2)C9—C10—C11—C121.2 (5)
N3—Cd1—N1—C266.9 (2)C10—C11—C12—C70.3 (4)
Cl2—Cd1—N1—C258.3 (3)C8—C7—C12—C110.5 (4)
Cl1—Cd1—N1—C2178.5 (2)C6—C7—C12—C11179.5 (3)
N1—Cd1—N3—C132.9 (2)C14—N3—C13—N40.4 (3)
Cl2—Cd1—N3—C13124.43 (19)Cd1—N3—C13—N4168.09 (16)
Cl1—Cd1—N3—C13107.8 (2)C15—N4—C13—N30.4 (3)
N1—Cd1—N3—C14168.3 (2)C16—N4—C13—N3179.4 (2)
Cl2—Cd1—N3—C1470.2 (2)C13—N3—C14—C150.3 (3)
Cl1—Cd1—N3—C1457.5 (2)Cd1—N3—C14—C15167.01 (19)
C2—N1—C1—N20.0 (3)N3—C14—C15—N40.1 (3)
Cd1—N1—C1—N2177.52 (17)C13—N4—C15—C140.2 (3)
C3—N2—C1—N10.1 (3)C16—N4—C15—C14179.2 (2)
C4—N2—C1—N1179.9 (2)C13—N4—C16—C17107.4 (3)
C1—N1—C2—C30.1 (3)C15—N4—C16—C1773.8 (3)
Cd1—N1—C2—C3177.3 (2)N4—C16—C17—C18178.5 (2)
N1—C2—C3—N20.2 (3)C16—C17—C18—O22.7 (4)
C1—N2—C3—C20.2 (3)C16—C17—C18—C19178.6 (2)
C4—N2—C3—C2179.9 (3)O2—C18—C19—C243.3 (4)
C1—N2—C4—C576.3 (3)C17—C18—C19—C24175.4 (2)
C3—N2—C4—C5104.0 (3)O2—C18—C19—C20178.2 (3)
N2—C4—C5—C6172.7 (2)C17—C18—C19—C203.1 (4)
C4—C5—C6—O14.9 (4)C24—C19—C20—C211.1 (4)
C4—C5—C6—C7174.0 (2)C18—C19—C20—C21177.4 (3)
O1—C6—C7—C12172.6 (3)C19—C20—C21—C220.8 (4)
C5—C6—C7—C128.5 (4)C20—C21—C22—C232.1 (5)
O1—C6—C7—C87.4 (4)C21—C22—C23—C241.5 (5)
C5—C6—C7—C8171.4 (2)C22—C23—C24—C190.4 (4)
C12—C7—C8—C90.4 (4)C20—C19—C24—C231.7 (4)
C6—C7—C8—C9179.5 (3)C18—C19—C24—C23176.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···Cl2i0.972.723.617 (3)155
C5—H5A···O2ii0.972.483.316 (3)145
C16—H16A···Cl1iii0.972.643.564 (3)160
Symmetry codes: (i) x+2, y1/2, z+1/2; (ii) x, y1, z; (iii) x, y+1, z.
 

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