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The structure of the title compound, [Cr(C14H10N2O)(CO)3], at 173 K has mol­ecules arranged in a herring-bone pattern. The side chain of the arenechromium unit is planar and tilted by approximately 24° to the benzene ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806029904/kp2047sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806029904/kp2047Isup2.hkl
Contains datablock I

CCDC reference: 621399

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.041
  • wR factor = 0.120
  • Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C15 .. 5.78 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cr1 - C15 .. 9.52 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cr1 - C16 .. 9.22 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cr1 - C17 .. 8.09 su PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C8 - C9 ... 1.42 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C17 H10 Cr N2 O4
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 69.13 From the CIF: _reflns_number_total 2700 From the CIF: _diffrn_reflns_limit_ max hkl 12. 16. 25. From the CIF: _diffrn_reflns_limit_ min hkl -12. -16. -25. TEST1: Expected hkl limits for theta max Calculated maximum hkl 16. 12. 25. Calculated minimum hkl -16. -12. -25.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: Proteum2 (Bruker, 2005); 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: ORTEP-3 (Farrugia, 1997) and RASTER3D (Merritt & Merritt, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

[η6-2-Benzoyl-2-(1,2-dihydropyridin-2-ylidene)acetonitrile] tricarbonylchromium(0) top
Crystal data top
[Cr(C14H10N2O)(CO)3]F(000) = 1456
Mr = 358.27Dx = 1.635 Mg m3
Orthorhombic, PbcaCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2abCell parameters from 7332 reflections
a = 13.6266 (4) Åθ = 4.3–68.8°
b = 10.3234 (3) ŵ = 6.71 mm1
c = 20.6939 (6) ÅT = 100 K
V = 2911.07 (15) Å3Block, yellow
Z = 80.12 × 0.06 × 0.03 mm
Data collection top
BrukerProteum
diffractometer
2700 independent reflections
Radiation source: fine-focus rotating anode2456 reflections with I > 2σ(I)
Osmic mirrors monochromatorRint = 0.057
area–detector scansθmax = 69.1°, θmin = 4.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1212
Tmin = 0.500, Tmax = 0.824k = 1616
55017 measured reflectionsl = 2525
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.041 w = 1/[σ2(Fo2) + (0.0675P)2 + 4.6385P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.120(Δ/σ)max < 0.001
S = 1.09Δρmax = 0.83 e Å3
2700 reflectionsΔρmin = 0.78 e Å3
221 parameters
Special details top

Experimental. 1H NMR (270 MHz) CDCl3: δ 17.3 (br s, 1H, NH), 7.91 (m, 2H, py), 7.60 (d, 1H, py, J = 9 Hz), 7.11 (t, 1H, py, J = 6 Hz), 6.23 (d, 2H, ArCr, J = 6 Hz), 5.50 (t, 1H, ArCr, J = 6 Hz), 5.31 (t, 2 H, ArCr, J = 6 Hz) p.p.m.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cr10.59011 (3)0.06496 (4)0.30904 (2)0.01675 (17)
C50.7234 (2)0.0573 (3)0.31046 (13)0.0207 (6)
H50.77430.06420.27920.025*
O30.43784 (17)0.0306 (2)0.20789 (12)0.0360 (5)
C40.6421 (2)0.1395 (3)0.30674 (13)0.0212 (6)
H40.63720.20110.27280.025*
O20.67466 (18)0.2441 (2)0.21079 (10)0.0304 (5)
C10.65634 (19)0.0461 (3)0.40701 (13)0.0168 (5)
C20.5744 (2)0.0394 (3)0.40325 (13)0.0180 (5)
H20.5240.03440.43480.022*
C30.5676 (2)0.1305 (3)0.35359 (13)0.0204 (6)
H30.51250.18660.35140.024*
C60.73069 (19)0.0360 (3)0.36029 (13)0.0180 (5)
H60.7860.0920.36210.022*
C150.6451 (2)0.1762 (3)0.24877 (14)0.0236 (6)
C160.4944 (2)0.0388 (3)0.24641 (15)0.0241 (6)
O10.56705 (13)0.17590 (19)0.47967 (9)0.0202 (4)
C70.65137 (19)0.1491 (3)0.45908 (12)0.0170 (5)
O40.46785 (17)0.2899 (2)0.35107 (11)0.0341 (5)
C100.73187 (19)0.3140 (2)0.52972 (12)0.0155 (5)
C90.83365 (19)0.1657 (2)0.46814 (12)0.0162 (5)
C80.73743 (19)0.2099 (2)0.48316 (12)0.0159 (5)
C170.5141 (2)0.2065 (3)0.33611 (13)0.0230 (6)
N20.64246 (16)0.3602 (2)0.54754 (10)0.0157 (5)
N10.91284 (16)0.1324 (2)0.45788 (12)0.0205 (5)
C120.8024 (2)0.4730 (3)0.60120 (13)0.0193 (5)
H120.85830.51150.62080.023*
C140.6295 (2)0.4600 (3)0.58872 (13)0.0173 (5)
H140.56510.48950.59840.021*
C130.7086 (2)0.5187 (3)0.61658 (13)0.0186 (5)
H130.70030.58890.64570.022*
C110.81490 (19)0.3729 (3)0.55798 (12)0.0178 (5)
H110.8790.34370.54720.021*
H150.597 (2)0.324 (3)0.5328 (16)0.014 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cr10.0159 (3)0.0171 (3)0.0173 (3)0.00033 (17)0.00043 (16)0.00074 (17)
C50.0165 (14)0.0245 (14)0.0210 (14)0.0067 (11)0.0005 (10)0.0042 (11)
O30.0273 (12)0.0434 (14)0.0372 (13)0.0033 (11)0.0086 (11)0.0100 (11)
C40.0230 (14)0.0179 (13)0.0228 (14)0.0059 (11)0.0025 (11)0.0048 (10)
O20.0495 (13)0.0226 (10)0.0191 (10)0.0067 (10)0.0021 (10)0.0000 (9)
C10.0156 (12)0.0185 (13)0.0163 (13)0.0032 (10)0.0028 (10)0.0003 (10)
C20.0169 (12)0.0192 (13)0.0179 (13)0.0007 (11)0.0012 (10)0.0028 (11)
C30.0211 (13)0.0168 (13)0.0232 (14)0.0008 (11)0.0034 (11)0.0024 (11)
C60.0131 (13)0.0221 (13)0.0188 (13)0.0023 (10)0.0002 (10)0.0013 (11)
C150.0201 (14)0.0245 (14)0.0263 (15)0.0049 (11)0.0015 (11)0.0126 (13)
C160.0237 (14)0.0207 (13)0.0280 (15)0.0072 (12)0.0065 (12)0.0038 (12)
O10.0131 (9)0.0256 (10)0.0219 (9)0.0008 (8)0.0027 (7)0.0060 (8)
C70.0171 (13)0.0185 (13)0.0153 (12)0.0005 (10)0.0007 (10)0.0011 (10)
O40.0390 (13)0.0274 (11)0.0360 (12)0.0110 (10)0.0049 (10)0.0057 (10)
C100.0158 (12)0.0168 (12)0.0139 (12)0.0022 (10)0.0012 (9)0.0026 (10)
C90.0195 (14)0.0156 (12)0.0137 (12)0.0015 (10)0.0010 (10)0.0004 (10)
C80.0161 (12)0.0169 (12)0.0147 (12)0.0015 (10)0.0016 (10)0.0006 (10)
C170.0219 (14)0.0326 (16)0.0146 (13)0.0052 (13)0.0062 (11)0.0044 (12)
N20.0124 (11)0.0189 (11)0.0157 (11)0.0011 (9)0.0009 (8)0.0004 (9)
N10.0160 (12)0.0237 (12)0.0219 (12)0.0015 (9)0.0001 (9)0.0033 (10)
C120.0175 (13)0.0209 (13)0.0195 (13)0.0030 (11)0.0031 (10)0.0003 (11)
C140.0186 (13)0.0175 (12)0.0160 (13)0.0023 (11)0.0023 (10)0.0002 (10)
C130.0208 (13)0.0182 (12)0.0169 (12)0.0013 (11)0.0006 (10)0.0019 (10)
C110.0156 (12)0.0208 (13)0.0170 (12)0.0016 (10)0.0005 (10)0.0013 (10)
Geometric parameters (Å, º) top
Cr1—C151.854 (3)C2—H20.95
Cr1—C161.859 (3)C3—H30.95
Cr1—C171.876 (3)C6—H60.95
Cr1—C62.210 (3)O1—C71.256 (3)
Cr1—C52.212 (3)C7—C81.420 (4)
Cr1—C42.227 (3)O4—C171.111 (4)
Cr1—C12.228 (3)C10—N21.360 (3)
Cr1—C22.238 (3)C10—C111.411 (4)
Cr1—C32.240 (3)C10—C81.445 (4)
C5—C41.397 (4)C9—N11.152 (3)
C5—C61.415 (4)C9—C81.423 (4)
C5—H50.95N2—C141.349 (3)
O3—C161.112 (4)N2—H150.79 (3)
C4—C31.407 (4)C12—C111.377 (4)
C4—H40.95C12—C131.399 (4)
O2—C151.127 (4)C12—H120.95
C1—C61.404 (4)C14—C131.365 (4)
C1—C21.425 (4)C14—H140.95
C1—C71.515 (4)C13—H130.95
C2—C31.396 (4)C11—H110.95
C15—Cr1—C1684.52 (12)C2—C1—C7116.0 (2)
C15—Cr1—C1786.66 (12)C6—C1—Cr170.86 (15)
C16—Cr1—C1786.18 (13)C2—C1—Cr171.77 (15)
C15—Cr1—C693.23 (11)C7—C1—Cr1124.59 (17)
C16—Cr1—C6157.44 (12)C3—C2—C1120.6 (2)
C17—Cr1—C6116.15 (11)C3—C2—Cr171.91 (16)
C15—Cr1—C591.75 (12)C1—C2—Cr171.00 (15)
C16—Cr1—C5120.19 (12)C3—C2—H2119.7
C17—Cr1—C5153.33 (11)C1—C2—H2119.7
C6—Cr1—C537.31 (10)Cr1—C2—H2130
C15—Cr1—C4116.37 (12)C2—C3—C4120.2 (3)
C16—Cr1—C494.08 (12)C2—C3—Cr171.76 (15)
C17—Cr1—C4156.91 (11)C4—C3—Cr171.15 (16)
C6—Cr1—C466.80 (10)C2—C3—H3119.9
C5—Cr1—C436.69 (11)C4—C3—H3119.9
C15—Cr1—C1120.18 (11)Cr1—C3—H3129.7
C16—Cr1—C1155.00 (11)C1—C6—C5120.1 (3)
C17—Cr1—C191.15 (11)C1—C6—Cr172.24 (15)
C6—Cr1—C136.90 (9)C5—C6—Cr171.44 (15)
C5—Cr1—C166.76 (10)C1—C6—H6119.9
C4—Cr1—C178.91 (10)C5—C6—H6119.9
C15—Cr1—C2157.39 (11)Cr1—C6—H6128.6
C16—Cr1—C2118.07 (11)O2—C15—Cr1177.0 (3)
C17—Cr1—C293.56 (11)O3—C16—Cr1175.9 (3)
C6—Cr1—C266.39 (10)O1—C7—C8122.6 (2)
C5—Cr1—C278.00 (10)O1—C7—C1115.9 (2)
C4—Cr1—C265.95 (10)C8—C7—C1121.5 (2)
C1—Cr1—C237.23 (10)N2—C10—C11117.0 (2)
C15—Cr1—C3152.95 (12)N2—C10—C8119.3 (2)
C16—Cr1—C393.45 (12)C11—C10—C8123.7 (2)
C17—Cr1—C3120.19 (11)N1—C9—C8177.5 (3)
C6—Cr1—C378.42 (10)C7—C8—C9122.9 (2)
C5—Cr1—C365.97 (10)C7—C8—C10121.3 (2)
C4—Cr1—C336.72 (10)C9—C8—C10115.6 (2)
C1—Cr1—C366.55 (10)O4—C17—Cr1178.6 (3)
C2—Cr1—C336.33 (10)C14—N2—C10123.9 (2)
C4—C5—C6120.6 (3)C14—N2—H15120 (2)
C4—C5—Cr172.23 (16)C10—N2—H15116 (2)
C6—C5—Cr171.25 (15)C11—C12—C13120.9 (2)
C4—C5—H5119.7C11—C12—H12119.6
C6—C5—H5119.7C13—C12—H12119.6
Cr1—C5—H5129.2N2—C14—C13120.1 (2)
C5—C4—C3119.6 (2)N2—C14—H14119.9
C5—C4—Cr171.08 (16)C13—C14—H14119.9
C3—C4—Cr172.13 (16)C14—C13—C12118.4 (2)
C5—C4—H4120.2C14—C13—H13120.8
C3—C4—H4120.2C12—C13—H13120.8
Cr1—C4—H4128.9C12—C11—C10119.6 (2)
C6—C1—C2118.8 (2)C12—C11—H11120.2
C6—C1—C7125.0 (2)C10—C11—H11120.2
C15—Cr1—C5—C4134.65 (17)C6—Cr1—C2—C129.83 (15)
C16—Cr1—C5—C450.0 (2)C5—Cr1—C2—C167.23 (16)
C17—Cr1—C5—C4139.3 (2)C4—Cr1—C2—C1103.83 (17)
C6—Cr1—C5—C4132.3 (2)C3—Cr1—C2—C1132.8 (2)
C1—Cr1—C5—C4103.06 (18)C1—C2—C3—C40.4 (4)
C2—Cr1—C5—C465.68 (16)Cr1—C2—C3—C454.1 (2)
C3—Cr1—C5—C429.47 (16)C1—C2—C3—Cr153.7 (2)
C15—Cr1—C5—C693.03 (17)C5—C4—C3—C20.5 (4)
C16—Cr1—C5—C6177.70 (17)Cr1—C4—C3—C254.4 (2)
C17—Cr1—C5—C67.0 (3)C5—C4—C3—Cr154.9 (2)
C4—Cr1—C5—C6132.3 (2)C15—Cr1—C3—C2139.8 (2)
C1—Cr1—C5—C629.27 (16)C16—Cr1—C3—C2135.54 (17)
C2—Cr1—C5—C666.65 (17)C17—Cr1—C3—C247.9 (2)
C3—Cr1—C5—C6102.85 (18)C6—Cr1—C3—C265.71 (16)
C6—C5—C4—C31.0 (4)C5—Cr1—C3—C2102.81 (18)
Cr1—C5—C4—C355.4 (2)C4—Cr1—C3—C2132.3 (2)
C6—C5—C4—Cr154.4 (2)C1—Cr1—C3—C228.93 (15)
C15—Cr1—C4—C552.53 (19)C15—Cr1—C3—C47.5 (3)
C16—Cr1—C4—C5138.43 (18)C16—Cr1—C3—C492.20 (18)
C17—Cr1—C4—C5131.7 (3)C17—Cr1—C3—C4179.79 (17)
C6—Cr1—C4—C529.18 (16)C6—Cr1—C3—C466.56 (16)
C1—Cr1—C4—C565.80 (16)C5—Cr1—C3—C429.45 (16)
C2—Cr1—C4—C5102.57 (17)C1—Cr1—C3—C4103.33 (18)
C3—Cr1—C4—C5131.3 (2)C2—Cr1—C3—C4132.3 (2)
C15—Cr1—C4—C3176.20 (17)C2—C1—C6—C50.3 (4)
C16—Cr1—C4—C390.30 (18)C7—C1—C6—C5174.5 (2)
C17—Cr1—C4—C30.5 (4)Cr1—C1—C6—C555.1 (2)
C6—Cr1—C4—C3102.08 (18)C2—C1—C6—Cr155.4 (2)
C5—Cr1—C4—C3131.3 (2)C7—C1—C6—Cr1119.4 (2)
C1—Cr1—C4—C365.47 (17)C4—C5—C6—C10.6 (4)
C2—Cr1—C4—C328.69 (16)Cr1—C5—C6—C155.5 (2)
C15—Cr1—C1—C648.2 (2)C4—C5—C6—Cr154.9 (2)
C16—Cr1—C1—C6141.5 (3)C15—Cr1—C6—C1139.78 (17)
C17—Cr1—C1—C6135.03 (17)C16—Cr1—C6—C1136.7 (3)
C5—Cr1—C1—C629.58 (16)C17—Cr1—C6—C151.92 (19)
C4—Cr1—C1—C665.96 (17)C5—Cr1—C6—C1131.6 (2)
C2—Cr1—C1—C6130.6 (2)C4—Cr1—C6—C1102.84 (18)
C3—Cr1—C1—C6102.32 (18)C2—Cr1—C6—C130.09 (15)
C15—Cr1—C1—C2178.82 (16)C3—Cr1—C6—C166.20 (16)
C16—Cr1—C1—C210.9 (3)C15—Cr1—C6—C588.65 (18)
C17—Cr1—C1—C294.38 (17)C16—Cr1—C6—C55.2 (4)
C6—Cr1—C1—C2130.6 (2)C17—Cr1—C6—C5176.51 (17)
C5—Cr1—C1—C2101.02 (17)C4—Cr1—C6—C528.72 (16)
C4—Cr1—C1—C264.64 (16)C1—Cr1—C6—C5131.6 (2)
C3—Cr1—C1—C228.28 (15)C2—Cr1—C6—C5101.48 (18)
C15—Cr1—C1—C771.7 (2)C3—Cr1—C6—C565.37 (17)
C16—Cr1—C1—C798.5 (3)C6—C1—C7—O1153.5 (3)
C17—Cr1—C1—C715.1 (2)C2—C1—C7—O121.4 (3)
C6—Cr1—C1—C7119.9 (3)Cr1—C1—C7—O163.6 (3)
C5—Cr1—C1—C7149.5 (2)C6—C1—C7—C827.2 (4)
C4—Cr1—C1—C7174.1 (2)C2—C1—C7—C8158.0 (2)
C2—Cr1—C1—C7109.5 (3)Cr1—C1—C7—C8117.0 (2)
C3—Cr1—C1—C7137.8 (2)O1—C7—C8—C9169.3 (2)
C6—C1—C2—C30.8 (4)C1—C7—C8—C910.1 (4)
C7—C1—C2—C3174.4 (2)O1—C7—C8—C104.8 (4)
Cr1—C1—C2—C354.1 (2)C1—C7—C8—C10175.9 (2)
C6—C1—C2—Cr154.9 (2)N2—C10—C8—C74.4 (4)
C7—C1—C2—Cr1120.3 (2)C11—C10—C8—C7176.3 (2)
C15—Cr1—C2—C3130.2 (3)N2—C10—C8—C9178.9 (2)
C16—Cr1—C2—C352.4 (2)C11—C10—C8—C91.9 (4)
C17—Cr1—C2—C3139.98 (17)C11—C10—N2—C141.9 (4)
C6—Cr1—C2—C3102.98 (18)C8—C10—N2—C14177.5 (2)
C5—Cr1—C2—C365.58 (17)C10—N2—C14—C131.8 (4)
C4—Cr1—C2—C328.98 (16)N2—C14—C13—C120.1 (4)
C1—Cr1—C2—C3132.8 (2)C11—C12—C13—C141.3 (4)
C15—Cr1—C2—C12.7 (4)C13—C12—C11—C101.2 (4)
C16—Cr1—C2—C1174.78 (16)N2—C10—C11—C120.3 (4)
C17—Cr1—C2—C187.21 (17)C8—C10—C11—C12179.0 (2)
 

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