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The title compound, [Cr(C15H14O)(CO)3], is a chromene complexed with tri­carbonyl­chromium and it exhibits photochromic properties. The molecular geometry is compared to that of two similar complexes. The analysis results indicate that complexation has minor effects on the chromene structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100006843/qa0298sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100006843/qa0298Isup2.hkl
Contains datablock I

CCDC reference: 146090

Computing details top

Data collection: CAD-4 Operations Manual (Enraf-Nonius, 1977); cell refinement: CAD-4 Operations Manual; data reduction: DATARED (Pèpe, 1979); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON (Spek, 1990).

(I) top
Crystal data top
[Cr(C15H14O)(CO)3]F(000) = 712
Mr = 346.29Dx = 1.456 Mg m3
Dm = 1.45 (2) Mg m3
Dm measured by Flotation in (Benzene/Chloroform)
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 12.190 (2) ÅCell parameters from 25 reflections
b = 9.147 (2) Åθ = 9–15°
c = 14.612 (3) ŵ = 0.74 mm1
β = 104.20 (2)°T = 293 K
V = 1579.5 (5) Å3Square platelet, red
Z = 40.32 × 0.30 × 0.21 mm
Data collection top
Nonius CAD-4
diffractometer
4072 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeθmax = 30.2°, θmin = 2.0°
Graphite monochromatorh = 1616
ω/2θ scansk = 012
Absorption correction: ψ scans
(North et al., 1968)
l = 020
Tmin = 0.785, Tmax = 0.8563 standard reflections every 60 min
4663 measured reflections intensity decay: none
4663 independent 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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073Only H-atom coordinates refined
S = 0.98Calculated w = 1/[σ2(Fo2) + (0.040P)2]
where P = (Fo2 + 2Fc2)/3
4663 reflections(Δ/σ)max = 0.002
250 parametersΔρmax = 0.42 e Å3
14 restraintsΔρmin = 0.26 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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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
Cr0.725047 (15)0.27169 (2)0.421771 (13)0.03160 (6)
C20.63706 (13)0.2134 (2)0.50202 (10)0.0525 (3)
O30.58353 (15)0.1779 (3)0.55139 (12)0.0980 (6)
C40.61716 (10)0.20193 (14)0.32023 (9)0.0377 (2)
O50.55113 (10)0.16002 (15)0.25553 (8)0.0598 (3)
C60.65063 (14)0.44741 (17)0.40515 (12)0.0523 (3)
O70.60292 (15)0.55714 (17)0.39262 (13)0.0905 (5)
C80.85745 (11)0.22875 (15)0.34544 (9)0.0397 (2)
C90.87721 (12)0.36545 (16)0.38713 (11)0.0453 (3)
C100.88708 (11)0.38202 (14)0.48535 (11)0.0434 (3)
C110.87876 (10)0.26017 (13)0.54063 (9)0.0363 (2)
C120.86641 (9)0.11498 (12)0.50096 (8)0.03060 (19)
C130.85386 (9)0.10027 (12)0.40071 (8)0.0316 (2)
C140.83557 (11)0.04192 (14)0.35979 (8)0.0376 (2)
C150.82969 (12)0.16109 (14)0.41282 (9)0.0392 (2)
C160.84096 (10)0.14649 (12)0.51141 (8)0.0338 (2)
C170.86168 (9)0.01307 (12)0.55651 (7)0.0310 (2)
C180.88723 (11)0.01345 (14)0.65950 (8)0.0372 (2)
C190.86368 (12)0.13166 (16)0.70411 (9)0.0426 (3)
C200.80350 (12)0.25997 (15)0.64990 (10)0.0432 (3)
O210.83591 (9)0.27235 (10)0.55959 (7)0.0422 (2)
C220.67646 (16)0.2406 (2)0.62840 (17)0.0607 (4)
C230.8397 (2)0.4047 (2)0.69920 (15)0.0618 (4)
H80.8465 (17)0.216 (2)0.2800 (14)0.053*
H90.8797 (15)0.449 (2)0.3494 (13)0.048*
H100.8964 (14)0.4869 (18)0.5119 (12)0.041*
H110.8836 (15)0.2632 (19)0.6048 (12)0.041*
H140.8304 (15)0.045 (2)0.2925 (13)0.048*
H150.8263 (15)0.2520 (18)0.3851 (12)0.040*
H180.9284 (15)0.069 (2)0.6932 (13)0.047*
H190.8833 (17)0.145 (2)0.7675 (14)0.058*
H2210.656 (2)0.228 (3)0.6854 (17)0.073*
H2220.662 (2)0.161 (3)0.5967 (17)0.073*
H2230.641 (2)0.311 (3)0.5929 (17)0.073*
H2310.9167 (17)0.414 (2)0.7127 (14)0.056*
H2320.8216 (17)0.393 (2)0.7576 (14)0.056*
H2330.7999 (17)0.481 (2)0.6597 (14)0.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cr0.03068 (9)0.03117 (9)0.03098 (9)0.00232 (6)0.00379 (6)0.00045 (6)
C20.0402 (6)0.0755 (10)0.0404 (6)0.0123 (7)0.0069 (5)0.0094 (7)
O30.0706 (9)0.1621 (18)0.0729 (9)0.0160 (11)0.0399 (8)0.0373 (11)
C40.0353 (5)0.0372 (5)0.0394 (5)0.0003 (4)0.0068 (4)0.0011 (4)
O50.0518 (6)0.0696 (7)0.0493 (6)0.0103 (5)0.0045 (5)0.0094 (5)
C60.0520 (7)0.0435 (7)0.0540 (8)0.0107 (6)0.0011 (6)0.0046 (6)
O70.0947 (11)0.0586 (8)0.1009 (12)0.0404 (8)0.0091 (9)0.0062 (8)
C80.0372 (5)0.0437 (6)0.0393 (6)0.0009 (5)0.0117 (4)0.0060 (5)
C90.0425 (6)0.0400 (6)0.0531 (7)0.0045 (5)0.0109 (5)0.0089 (5)
C100.0394 (6)0.0336 (5)0.0535 (7)0.0064 (5)0.0040 (5)0.0022 (5)
C110.0345 (5)0.0345 (5)0.0348 (5)0.0014 (4)0.0015 (4)0.0053 (4)
C120.0275 (4)0.0311 (5)0.0307 (4)0.0006 (4)0.0024 (3)0.0041 (4)
C130.0307 (5)0.0325 (5)0.0309 (5)0.0020 (4)0.0060 (4)0.0013 (4)
C140.0426 (6)0.0391 (6)0.0303 (5)0.0033 (5)0.0077 (4)0.0059 (4)
C150.0470 (6)0.0331 (5)0.0362 (5)0.0011 (5)0.0075 (5)0.0092 (4)
C160.0354 (5)0.0295 (5)0.0360 (5)0.0037 (4)0.0077 (4)0.0014 (4)
C170.0303 (4)0.0323 (5)0.0285 (4)0.0037 (4)0.0036 (4)0.0021 (4)
C180.0397 (5)0.0391 (6)0.0304 (5)0.0034 (4)0.0036 (4)0.0037 (4)
C190.0470 (6)0.0473 (7)0.0338 (5)0.0054 (5)0.0108 (5)0.0025 (5)
C200.0482 (7)0.0399 (6)0.0455 (6)0.0040 (5)0.0192 (5)0.0046 (5)
O210.0555 (5)0.0306 (4)0.0432 (4)0.0048 (4)0.0174 (4)0.0005 (3)
C220.0490 (8)0.0613 (10)0.0749 (12)0.0023 (7)0.0212 (8)0.0048 (9)
C230.0846 (13)0.0469 (8)0.0621 (10)0.0109 (8)0.0337 (9)0.0153 (7)
Geometric parameters (Å, º) top
Cr—C61.8323 (15)C12—C131.4412 (15)
Cr—C41.8387 (13)C13—C141.4259 (16)
Cr—C21.8510 (16)C14—C151.3494 (19)
Cr—C102.2097 (13)C14—H140.970 (18)
Cr—C82.2105 (13)C15—C161.4195 (17)
Cr—C92.2120 (14)C15—H150.921 (16)
Cr—C112.2230 (13)C16—O211.3587 (15)
Cr—C132.2926 (11)C16—C171.3804 (15)
Cr—C122.3205 (11)C17—C181.4601 (16)
C2—O31.133 (2)C18—C191.3298 (19)
C4—O51.1468 (17)C18—H180.973 (18)
C6—O71.152 (2)C19—C201.503 (2)
C8—C91.386 (2)C19—H190.905 (19)
C8—C131.4327 (17)C20—O211.4718 (16)
C8—H80.940 (19)C20—C221.513 (2)
C9—C101.419 (2)C20—C231.520 (2)
C9—H90.946 (18)C22—H2210.93 (2)
C10—C111.3947 (19)C22—H2220.85 (2)
C10—H101.030 (17)C22—H2230.87 (2)
C11—C121.4420 (15)C23—H2310.91 (2)
C11—H110.926 (17)C23—H2320.939 (19)
C12—C171.4343 (16)C23—H2330.96 (2)
C6—Cr—C487.97 (6)Cr—C10—H10126.0 (10)
C6—Cr—C289.52 (8)C10—C11—C12121.23 (11)
C4—Cr—C290.02 (7)C10—C11—Cr71.14 (7)
C6—Cr—C1091.00 (6)C12—C11—Cr75.21 (6)
C4—Cr—C10152.42 (6)C10—C11—H11124.6 (11)
C2—Cr—C10117.53 (7)C12—C11—H11114.2 (11)
C6—Cr—C8119.21 (7)Cr—C11—H11128.5 (11)
C4—Cr—C889.85 (6)C17—C12—C13119.33 (10)
C2—Cr—C8151.25 (7)C17—C12—C11122.64 (10)
C10—Cr—C866.75 (6)C13—C12—C11117.98 (10)
C6—Cr—C992.59 (7)C17—C12—Cr131.19 (8)
C4—Cr—C9115.08 (6)C13—C12—Cr70.74 (6)
C2—Cr—C9154.86 (7)C11—C12—Cr67.86 (6)
C10—Cr—C937.43 (6)C14—C13—C8122.35 (11)
C8—Cr—C936.52 (5)C14—C13—C12118.56 (10)
C6—Cr—C11116.11 (6)C8—C13—C12119.08 (11)
C4—Cr—C11155.92 (5)C14—C13—Cr129.66 (8)
C2—Cr—C1189.99 (6)C8—C13—Cr68.36 (7)
C10—Cr—C1136.68 (5)C12—C13—Cr72.85 (6)
C8—Cr—C1178.81 (5)C15—C14—C13121.39 (11)
C9—Cr—C1166.65 (5)C15—C14—H14124.1 (11)
C6—Cr—C13156.25 (7)C13—C14—H14114.5 (11)
C4—Cr—C1391.85 (5)C14—C15—C16120.08 (11)
C2—Cr—C13114.24 (6)C14—C15—H15118.7 (11)
C10—Cr—C1378.33 (5)C16—C15—H15120.9 (11)
C8—Cr—C1337.05 (4)O21—C16—C17121.87 (11)
C9—Cr—C1366.05 (5)O21—C16—C15116.15 (10)
C11—Cr—C1366.34 (4)C17—C16—C15121.90 (11)
C6—Cr—C12152.99 (6)C16—C17—C12118.68 (10)
C4—Cr—C12118.99 (5)C16—C17—C18117.24 (10)
C2—Cr—C1288.92 (6)C12—C17—C18123.86 (10)
C10—Cr—C1266.08 (5)C19—C18—C17119.35 (12)
C8—Cr—C1266.23 (5)C19—C18—H18122.1 (11)
C9—Cr—C1277.98 (5)C17—C18—H18118.2 (11)
C11—Cr—C1236.93 (4)C18—C19—C20120.85 (12)
C13—Cr—C1236.40 (4)C18—C19—H19125.0 (14)
O3—C2—Cr179.8 (2)C20—C19—H19114.2 (14)
O5—C4—Cr178.42 (13)O21—C20—C19109.21 (11)
O7—C6—Cr178.48 (16)O21—C20—C22107.99 (13)
C9—C8—C13121.23 (12)C19—C20—C22111.12 (13)
C9—C8—Cr71.80 (8)O21—C20—C23104.31 (12)
C13—C8—Cr74.59 (7)C19—C20—C23112.52 (14)
C9—C8—H8121.8 (12)C22—C20—C23111.35 (15)
C13—C8—H8116.9 (12)C16—O21—C20117.10 (9)
Cr—C8—H8126.6 (12)C20—C22—H221108.1 (16)
C8—C9—C10120.23 (12)C20—C22—H222105.8 (17)
C8—C9—Cr71.68 (8)H221—C22—H222109 (2)
C10—C9—Cr71.20 (8)C20—C22—H223111.8 (17)
C8—C9—H9119.8 (11)H221—C22—H223115 (2)
C10—C9—H9119.8 (11)H222—C22—H223107 (2)
Cr—C9—H9126.5 (11)C20—C23—H231110.3 (14)
C11—C10—C9120.02 (12)C20—C23—H232102.9 (13)
C11—C10—Cr72.18 (7)H231—C23—H232105.8 (18)
C9—C10—Cr71.38 (8)C20—C23—H233107.6 (13)
C11—C10—H10122.9 (10)H231—C23—H233114.0 (18)
C9—C10—H10117.1 (10)H232—C23—H233115.8 (18)
C6—Cr—C2—O398 (50)C10—C11—C12—C17177.72 (11)
C4—Cr—C2—O3174 (100)Cr—C11—C12—C17125.71 (10)
C10—Cr—C2—O37 (50)C10—C11—C12—C134.83 (17)
C8—Cr—C2—O384 (50)Cr—C11—C12—C1351.73 (9)
C9—Cr—C2—O33 (50)C10—C11—C12—Cr56.57 (11)
C11—Cr—C2—O318 (50)C6—Cr—C12—C17110.08 (16)
C13—Cr—C2—O382 (50)C4—Cr—C12—C1766.16 (11)
C12—Cr—C2—O355 (50)C2—Cr—C12—C1723.27 (11)
C6—Cr—C4—O579 (5)C10—Cr—C12—C17144.21 (11)
C2—Cr—C4—O5169 (5)C8—Cr—C12—C17141.85 (11)
C10—Cr—C4—O59 (5)C9—Cr—C12—C17178.33 (11)
C8—Cr—C4—O540 (5)C11—Cr—C12—C17114.69 (13)
C9—Cr—C4—O513 (5)C13—Cr—C12—C17112.57 (12)
C11—Cr—C4—O5101 (5)C6—Cr—C12—C13137.34 (15)
C13—Cr—C4—O577 (5)C4—Cr—C12—C1346.41 (8)
C12—Cr—C4—O5102 (5)C2—Cr—C12—C13135.84 (8)
C4—Cr—C6—O726 (7)C10—Cr—C12—C13103.22 (8)
C2—Cr—C6—O7116 (7)C8—Cr—C12—C1329.27 (7)
C10—Cr—C6—O7127 (7)C9—Cr—C12—C1365.76 (7)
C8—Cr—C6—O763 (7)C11—Cr—C12—C13132.74 (10)
C9—Cr—C6—O789 (7)C6—Cr—C12—C114.60 (17)
C11—Cr—C6—O7154 (7)C4—Cr—C12—C11179.15 (8)
C13—Cr—C6—O764 (7)C2—Cr—C12—C1191.42 (9)
C12—Cr—C6—O7158 (7)C10—Cr—C12—C1129.52 (8)
C6—Cr—C8—C948.10 (10)C8—Cr—C12—C11103.47 (8)
C4—Cr—C8—C9135.69 (9)C9—Cr—C12—C1166.98 (8)
C2—Cr—C8—C9134.53 (13)C13—Cr—C12—C11132.74 (10)
C10—Cr—C8—C929.29 (8)C9—C8—C13—C14178.93 (12)
C11—Cr—C8—C965.70 (8)Cr—C8—C13—C14124.16 (11)
C13—Cr—C8—C9131.05 (11)C9—C8—C13—C122.60 (18)
C12—Cr—C8—C9102.26 (9)Cr—C8—C13—C1254.30 (9)
C6—Cr—C8—C13179.14 (8)C9—C8—C13—Cr56.91 (11)
C4—Cr—C8—C1393.26 (8)C17—C12—C13—C140.81 (16)
C2—Cr—C8—C133.48 (16)C11—C12—C13—C14176.72 (10)
C10—Cr—C8—C13101.76 (8)Cr—C12—C13—C14126.34 (10)
C9—Cr—C8—C13131.05 (11)C17—C12—C13—C8179.34 (10)
C11—Cr—C8—C1365.35 (7)C11—C12—C13—C81.80 (16)
C12—Cr—C8—C1328.79 (6)Cr—C12—C13—C852.19 (9)
C13—C8—C9—C104.1 (2)C17—C12—C13—Cr127.15 (10)
Cr—C8—C9—C1054.13 (12)C11—C12—C13—Cr50.38 (9)
C13—C8—C9—Cr58.23 (11)C6—Cr—C13—C14116.61 (16)
C6—Cr—C9—C8139.44 (9)C4—Cr—C13—C1427.45 (11)
C4—Cr—C9—C850.47 (9)C2—Cr—C13—C1463.40 (12)
C2—Cr—C9—C8126.18 (16)C10—Cr—C13—C14178.53 (11)
C10—Cr—C9—C8132.30 (12)C8—Cr—C13—C14114.76 (13)
C11—Cr—C9—C8103.15 (9)C9—Cr—C13—C14144.17 (12)
C13—Cr—C9—C829.81 (7)C11—Cr—C13—C14142.01 (12)
C12—Cr—C9—C866.12 (8)C12—Cr—C13—C14113.21 (13)
C6—Cr—C9—C1088.26 (9)C6—Cr—C13—C81.85 (17)
C4—Cr—C9—C10177.23 (8)C4—Cr—C13—C887.31 (8)
C2—Cr—C9—C106.12 (19)C2—Cr—C13—C8178.16 (9)
C8—Cr—C9—C10132.30 (12)C10—Cr—C13—C866.71 (8)
C11—Cr—C9—C1029.15 (8)C9—Cr—C13—C829.41 (8)
C13—Cr—C9—C10102.49 (9)C11—Cr—C13—C8103.23 (8)
C12—Cr—C9—C1066.18 (8)C12—Cr—C13—C8132.03 (10)
C8—C9—C10—C111.1 (2)C6—Cr—C13—C12130.18 (14)
Cr—C9—C10—C1155.41 (11)C4—Cr—C13—C12140.66 (7)
C8—C9—C10—Cr54.36 (12)C2—Cr—C13—C1249.80 (9)
C6—Cr—C10—C11135.52 (9)C10—Cr—C13—C1265.32 (7)
C4—Cr—C10—C11136.94 (11)C8—Cr—C13—C12132.03 (10)
C2—Cr—C10—C1145.55 (11)C9—Cr—C13—C12102.62 (8)
C8—Cr—C10—C11102.90 (9)C11—Cr—C13—C1228.80 (6)
C9—Cr—C10—C11131.52 (12)C8—C13—C14—C15178.33 (12)
C13—Cr—C10—C1165.87 (8)C12—C13—C14—C150.14 (18)
C12—Cr—C10—C1129.71 (7)Cr—C13—C14—C1590.73 (14)
C6—Cr—C10—C992.95 (10)C13—C14—C15—C160.5 (2)
C4—Cr—C10—C95.42 (16)C14—C15—C16—O21178.91 (12)
C2—Cr—C10—C9177.07 (9)C14—C15—C16—C172.13 (19)
C8—Cr—C10—C928.63 (8)O21—C16—C17—C12179.65 (10)
C11—Cr—C10—C9131.52 (12)C15—C16—C17—C123.05 (17)
C13—Cr—C10—C965.66 (8)O21—C16—C17—C184.84 (17)
C12—Cr—C10—C9101.81 (9)C15—C16—C17—C18171.75 (11)
C9—C10—C11—C123.47 (19)C13—C12—C17—C162.37 (16)
Cr—C10—C11—C1258.50 (10)C11—C12—C17—C16175.04 (11)
C9—C10—C11—Cr55.03 (12)Cr—C12—C17—C1687.00 (13)
C6—Cr—C11—C1051.27 (11)C13—C12—C17—C18172.07 (10)
C4—Cr—C11—C10129.24 (13)C11—C12—C17—C1810.52 (17)
C2—Cr—C11—C10140.73 (10)Cr—C12—C17—C1898.56 (12)
C8—Cr—C11—C1065.92 (9)C16—C17—C18—C1915.90 (17)
C9—Cr—C11—C1029.71 (8)C12—C17—C18—C19169.58 (12)
C13—Cr—C11—C10102.64 (9)C17—C18—C19—C204.56 (19)
C12—Cr—C11—C10131.05 (12)C18—C19—C20—O2132.53 (17)
C6—Cr—C11—C12177.67 (9)C18—C19—C20—C2286.50 (17)
C4—Cr—C11—C121.81 (16)C18—C19—C20—C23147.86 (14)
C2—Cr—C11—C1288.22 (9)C17—C16—O21—C2026.14 (17)
C10—Cr—C11—C12131.05 (12)C15—C16—O21—C20157.08 (12)
C8—Cr—C11—C1265.13 (7)C19—C20—O21—C1642.78 (15)
C9—Cr—C11—C12101.35 (8)C22—C20—O21—C1678.18 (15)
C13—Cr—C11—C1228.42 (6)C23—C20—O21—C16163.28 (14)
 

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