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Colorless crystals of the title compound, C29H24NO5P, were synthesized by the reaction of triphenyl­phosphine, an iron porphyrin complex and 4-nitro­benzyl 2-diazo-3-oxobutanoate at 353 K. All bond distances and angles are within normal ranges and there are no notable inter­actions between neighboring mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806001280/sg6053sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806001280/sg6053Isup2.hkl
Contains datablock I

CCDC reference: 298537

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.054
  • wR factor = 0.106
  • Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C11
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2003).

4-Nitrobenzyl 3-oxo-2-(triphenylphosphoranylidene)butanoate top
Crystal data top
C29H24NO5PF(000) = 2080
Mr = 497.46Dx = 1.339 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 15308 reflections
a = 39.826 (3) Åθ = 6.2–55.1°
b = 8.1857 (6) ŵ = 0.15 mm1
c = 15.1786 (10) ÅT = 293 K
β = 93.928 (10)°Block, colorless
V = 4936.6 (6) Å30.3 × 0.1 × 0.1 mm
Z = 8
Data collection top
Rigaku R-AXIS RAPID
diffractometer
5612 independent reflections
Radiation source: fine-focus sealed tube3278 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.067
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 5149
Tmin = 0.955, Tmax = 0.985k = 109
22380 measured reflectionsl = 1919
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0028P)2 + 8.1979P]
where P = (Fo2 + 2Fc2)/3
5612 reflections(Δ/σ)max = 0.001
325 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.33 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
P10.903188 (15)0.80248 (8)0.75506 (4)0.03641 (15)
O10.68538 (6)0.0416 (3)0.9153 (2)0.1117 (10)
O20.72881 (7)0.1037 (3)0.8955 (2)0.1170 (11)
O30.82377 (4)0.5822 (2)0.84116 (14)0.0577 (5)
O40.82982 (4)0.8480 (2)0.81299 (14)0.0625 (6)
O50.92858 (4)0.5564 (2)0.86107 (12)0.0538 (5)
N10.71476 (7)0.0276 (4)0.8996 (2)0.0761 (8)
C10.73449 (7)0.1767 (4)0.88493 (19)0.0551 (7)
C20.71879 (7)0.3242 (4)0.8920 (2)0.0686 (9)
H2A0.69620.33020.90390.082*
C30.73744 (7)0.4640 (4)0.8810 (2)0.0641 (9)
H3A0.72720.56540.88520.077*
C40.77104 (6)0.4566 (3)0.86383 (18)0.0483 (7)
C50.78543 (7)0.3049 (4)0.8567 (2)0.0660 (9)
H5A0.80800.29800.84480.079*
C60.76756 (7)0.1627 (4)0.8665 (2)0.0674 (9)
H6A0.77760.06100.86080.081*
C70.78924 (6)0.6152 (3)0.8559 (2)0.0547 (7)
H7A0.77900.67800.80700.066*
H7B0.78790.67850.90950.066*
C80.84275 (6)0.7143 (3)0.82153 (16)0.0426 (6)
C90.87800 (6)0.6776 (3)0.81574 (16)0.0394 (6)
C100.89736 (6)0.5502 (3)0.86031 (17)0.0435 (6)
C110.88143 (7)0.4104 (3)0.9073 (2)0.0624 (8)
H11A0.89870.33960.93270.094*
H11B0.86700.34990.86580.094*
H11C0.86840.45270.95320.094*
C120.93008 (6)0.9408 (3)0.81988 (17)0.0419 (6)
C130.94545 (7)1.0725 (4)0.7812 (2)0.0662 (8)
H13A0.94311.08630.72020.079*
C140.96411 (9)1.1826 (4)0.8329 (3)0.0873 (11)
H14A0.97471.27000.80710.105*
C150.96692 (9)1.1622 (5)0.9231 (3)0.0929 (13)
H15A0.97891.23820.95820.111*
C160.95246 (8)1.0328 (5)0.9616 (2)0.0811 (11)
H16A0.95531.01861.02240.097*
C170.93353 (7)0.9221 (4)0.91064 (19)0.0577 (7)
H17A0.92310.83520.93730.069*
C180.87957 (6)0.9357 (3)0.67805 (16)0.0388 (6)
C190.86538 (6)1.0788 (3)0.70863 (19)0.0495 (7)
H19A0.86711.10250.76870.059*
C200.84884 (7)1.1852 (3)0.6505 (2)0.0598 (8)
H20A0.83971.28100.67140.072*
C210.84584 (7)1.1507 (4)0.5623 (2)0.0653 (9)
H21A0.83451.22290.52340.078*
C220.85943 (7)1.0102 (4)0.5307 (2)0.0622 (8)
H22A0.85730.98720.47060.075*
C230.87640 (6)0.9019 (3)0.58902 (17)0.0483 (6)
H23A0.88560.80650.56770.058*
C240.92831 (6)0.6734 (3)0.68888 (16)0.0441 (6)
C250.96181 (7)0.7030 (4)0.67762 (19)0.0612 (8)
H25A0.97250.79410.70340.073*
C260.97961 (8)0.5944 (5)0.6270 (2)0.0837 (12)
H26A1.00240.61120.62010.100*
C270.96329 (11)0.4625 (5)0.5873 (2)0.0909 (13)
H27A0.97500.39280.55200.109*
C280.93018 (10)0.4326 (4)0.5991 (2)0.0808 (11)
H28A0.91960.34180.57300.097*
C290.91269 (8)0.5365 (3)0.64935 (19)0.0604 (8)
H29A0.89010.51580.65740.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0351 (3)0.0350 (3)0.0393 (3)0.0001 (3)0.0040 (2)0.0015 (3)
O10.0750 (16)0.0792 (18)0.184 (3)0.0394 (15)0.0352 (18)0.0183 (18)
O20.098 (2)0.0490 (15)0.206 (3)0.0193 (14)0.027 (2)0.0099 (18)
O30.0382 (9)0.0439 (10)0.0927 (15)0.0076 (9)0.0158 (9)0.0083 (10)
O40.0517 (11)0.0439 (11)0.0937 (17)0.0030 (9)0.0188 (10)0.0137 (11)
O50.0471 (10)0.0550 (11)0.0586 (12)0.0029 (9)0.0004 (9)0.0120 (10)
N10.0694 (18)0.0596 (18)0.100 (2)0.0290 (16)0.0130 (16)0.0101 (16)
C10.0501 (15)0.0534 (17)0.0622 (19)0.0191 (14)0.0075 (13)0.0038 (15)
C20.0418 (15)0.061 (2)0.104 (3)0.0132 (15)0.0116 (16)0.0069 (19)
C30.0426 (15)0.0498 (17)0.101 (3)0.0054 (14)0.0160 (15)0.0033 (17)
C40.0395 (13)0.0491 (16)0.0567 (18)0.0069 (13)0.0057 (12)0.0022 (13)
C50.0422 (15)0.0539 (18)0.104 (3)0.0077 (15)0.0184 (15)0.0012 (18)
C60.0558 (17)0.0471 (17)0.100 (3)0.0065 (15)0.0112 (17)0.0049 (17)
C70.0408 (14)0.0493 (16)0.075 (2)0.0056 (13)0.0115 (13)0.0051 (15)
C80.0444 (14)0.0424 (15)0.0417 (15)0.0100 (13)0.0074 (11)0.0012 (12)
C90.0396 (12)0.0355 (13)0.0432 (14)0.0045 (11)0.0038 (10)0.0023 (11)
C100.0464 (14)0.0423 (14)0.0421 (15)0.0032 (12)0.0041 (11)0.0027 (12)
C110.0625 (18)0.0531 (17)0.072 (2)0.0023 (15)0.0054 (15)0.0219 (16)
C120.0345 (12)0.0462 (15)0.0453 (16)0.0019 (12)0.0044 (11)0.0035 (12)
C130.071 (2)0.0608 (19)0.067 (2)0.0251 (17)0.0050 (16)0.0017 (16)
C140.087 (2)0.076 (2)0.101 (3)0.044 (2)0.019 (2)0.012 (2)
C150.078 (2)0.104 (3)0.097 (3)0.043 (2)0.012 (2)0.043 (3)
C160.081 (2)0.099 (3)0.062 (2)0.026 (2)0.0082 (18)0.018 (2)
C170.0609 (17)0.0591 (18)0.0524 (19)0.0114 (15)0.0013 (14)0.0042 (15)
C180.0369 (12)0.0361 (13)0.0437 (15)0.0006 (11)0.0046 (10)0.0054 (11)
C190.0558 (16)0.0414 (14)0.0519 (17)0.0064 (13)0.0081 (13)0.0017 (13)
C200.0565 (17)0.0451 (16)0.079 (2)0.0154 (14)0.0137 (15)0.0122 (16)
C210.0587 (18)0.066 (2)0.071 (2)0.0151 (16)0.0024 (16)0.0262 (17)
C220.0585 (17)0.083 (2)0.0447 (17)0.0118 (17)0.0053 (13)0.0120 (16)
C230.0446 (14)0.0553 (16)0.0456 (16)0.0098 (13)0.0079 (12)0.0026 (13)
C240.0458 (14)0.0476 (15)0.0391 (15)0.0136 (13)0.0051 (11)0.0080 (12)
C250.0484 (15)0.080 (2)0.0552 (18)0.0161 (16)0.0047 (13)0.0099 (17)
C260.0571 (19)0.131 (3)0.065 (2)0.041 (2)0.0194 (17)0.019 (2)
C270.108 (3)0.108 (3)0.059 (2)0.064 (3)0.023 (2)0.003 (2)
C280.113 (3)0.066 (2)0.065 (2)0.031 (2)0.015 (2)0.0119 (18)
C290.077 (2)0.0516 (17)0.0528 (19)0.0147 (16)0.0051 (15)0.0067 (14)
Geometric parameters (Å, º) top
P1—C91.740 (2)C13—C141.379 (4)
P1—C121.803 (2)C13—H13A0.9300
P1—C241.807 (3)C14—C151.376 (5)
P1—C181.814 (2)C14—H14A0.9300
O1—N11.215 (3)C15—C161.357 (5)
O2—N11.216 (3)C15—H15A0.9300
O3—C81.364 (3)C16—C171.381 (4)
O3—C71.434 (3)C16—H16A0.9300
O4—C81.213 (3)C17—H17A0.9300
O5—C101.244 (3)C18—C231.377 (3)
N1—C11.476 (4)C18—C191.394 (3)
C1—C21.367 (4)C19—C201.375 (4)
C1—C61.370 (4)C19—H19A0.9300
C2—C31.381 (4)C20—C211.366 (4)
C2—H2A0.9300C20—H20A0.9300
C3—C41.382 (3)C21—C221.371 (4)
C3—H3A0.9300C21—H21A0.9300
C4—C51.375 (4)C22—C231.394 (4)
C4—C71.496 (3)C22—H22A0.9300
C5—C61.378 (4)C23—H23A0.9300
C5—H5A0.9300C24—C251.378 (3)
C6—H6A0.9300C24—C291.398 (4)
C7—H7A0.9700C25—C261.400 (4)
C7—H7B0.9700C25—H25A0.9300
C8—C91.444 (3)C26—C271.376 (5)
C9—C101.438 (3)C26—H26A0.9300
C10—C111.511 (3)C27—C281.365 (5)
C11—H11A0.9600C27—H27A0.9300
C11—H11B0.9600C28—C291.364 (4)
C11—H11C0.9600C28—H28A0.9300
C12—C171.383 (4)C29—H29A0.9300
C12—C131.390 (4)
C9—P1—C12115.0 (1)C14—C13—C12120.2 (3)
C9—P1—C24108.2 (1)C14—C13—H13A119.9
C12—P1—C24109.9 (1)C12—C13—H13A119.9
C9—P1—C18113.7 (1)C15—C14—C13119.4 (3)
C12—P1—C18103.7 (1)C15—C14—H14A120.3
C24—P1—C18106.0 (1)C13—C14—H14A120.3
C8—O3—C7115.9 (2)C16—C15—C14121.0 (3)
O1—N1—O2123.1 (3)C16—C15—H15A119.5
O1—N1—C1118.8 (3)C14—C15—H15A119.5
O2—N1—C1118.1 (3)C15—C16—C17120.1 (3)
C2—C1—C6122.7 (3)C15—C16—H16A119.9
C2—C1—N1117.8 (3)C17—C16—H16A119.9
C6—C1—N1119.4 (3)C16—C17—C12119.9 (3)
C1—C2—C3118.0 (3)C16—C17—H17A120.1
C1—C2—H2A121.0C12—C17—H17A120.1
C3—C2—H2A121.0C23—C18—C19118.9 (2)
C2—C3—C4121.5 (3)C23—C18—P1121.4 (2)
C2—C3—H3A119.2C19—C18—P1119.7 (2)
C4—C3—H3A119.2C20—C19—C18120.4 (3)
C5—C4—C3117.9 (2)C20—C19—H19A119.8
C5—C4—C7124.8 (2)C18—C19—H19A119.8
C3—C4—C7117.3 (2)C21—C20—C19120.3 (3)
C4—C5—C6122.2 (2)C21—C20—H20A119.9
C4—C5—H5A118.9C19—C20—H20A119.9
C6—C5—H5A118.9C20—C21—C22120.4 (3)
C1—C6—C5117.5 (3)C20—C21—H21A119.8
C1—C6—H6A121.2C22—C21—H21A119.8
C5—C6—H6A121.2C21—C22—C23119.8 (3)
O3—C7—C4108.9 (2)C21—C22—H22A120.1
O3—C7—H7A109.9C23—C22—H22A120.1
C4—C7—H7A109.9C18—C23—C22120.2 (3)
O3—C7—H7B109.9C18—C23—H23A119.9
C4—C7—H7B109.9C22—C23—H23A119.9
H7A—C7—H7B108.3C25—C24—C29119.6 (3)
O4—C8—O3120.1 (2)C25—C24—P1122.9 (2)
O4—C8—C9126.1 (2)C29—C24—P1117.4 (2)
O3—C8—C9113.8 (2)C24—C25—C26119.2 (3)
C10—C9—C8127.9 (2)C24—C25—H25A120.4
C10—C9—P1111.4 (2)C26—C25—H25A120.4
C8—C9—P1120.6 (2)C27—C26—C25119.8 (3)
O5—C10—C9118.6 (2)C27—C26—H26A120.1
O5—C10—C11118.6 (2)C25—C26—H26A120.1
C9—C10—C11122.8 (2)C28—C27—C26121.0 (3)
C10—C11—H11A109.5C28—C27—H27A119.5
C10—C11—H11B109.5C26—C27—H27A119.5
H11A—C11—H11B109.5C29—C28—C27119.8 (4)
C10—C11—H11C109.5C29—C28—H28A120.1
H11A—C11—H11C109.5C27—C28—H28A120.1
H11B—C11—H11C109.5C28—C29—C24120.7 (3)
C17—C12—C13119.4 (3)C28—C29—H29A119.7
C17—C12—P1119.2 (2)C24—C29—H29A119.7
C13—C12—P1121.2 (2)
O1—N1—C1—C21.7 (5)C18—P1—C12—C1339.9 (2)
O2—N1—C1—C2178.2 (3)C17—C12—C13—C140.4 (4)
O1—N1—C1—C6179.5 (3)P1—C12—C13—C14175.7 (3)
O2—N1—C1—C60.6 (5)C12—C13—C14—C151.0 (5)
C6—C1—C2—C30.7 (5)C13—C14—C15—C162.0 (6)
N1—C1—C2—C3178.1 (3)C14—C15—C16—C172.4 (6)
C1—C2—C3—C40.4 (5)C15—C16—C17—C121.8 (5)
C2—C3—C4—C50.9 (5)C13—C12—C17—C160.8 (4)
C2—C3—C4—C7178.1 (3)P1—C12—C17—C16176.2 (2)
C3—C4—C5—C60.3 (5)C9—P1—C18—C23102.9 (2)
C7—C4—C5—C6178.6 (3)C12—P1—C18—C23131.5 (2)
C2—C1—C6—C51.3 (5)C24—P1—C18—C2315.8 (2)
N1—C1—C6—C5177.5 (3)C9—P1—C18—C1979.6 (2)
C4—C5—C6—C10.7 (5)C12—P1—C18—C1946.0 (2)
C8—O3—C7—C4172.1 (2)C24—P1—C18—C19161.6 (2)
C5—C4—C7—O30.9 (4)C23—C18—C19—C200.8 (4)
C3—C4—C7—O3178.1 (3)P1—C18—C19—C20176.8 (2)
C7—O3—C8—O43.7 (4)C18—C19—C20—C210.7 (4)
C7—O3—C8—C9174.3 (2)C19—C20—C21—C220.3 (4)
O4—C8—C9—C10150.1 (3)C20—C21—C22—C230.0 (4)
O3—C8—C9—C1027.8 (4)C19—C18—C23—C220.4 (4)
O4—C8—C9—P125.2 (4)P1—C18—C23—C22177.0 (2)
O3—C8—C9—P1156.88 (18)C21—C22—C23—C180.0 (4)
C12—P1—C9—C1073.8 (2)C9—P1—C24—C25138.5 (2)
C24—P1—C9—C1049.4 (2)C12—P1—C24—C2512.3 (3)
C18—P1—C9—C10166.85 (17)C18—P1—C24—C2599.1 (2)
C12—P1—C9—C8102.2 (2)C9—P1—C24—C2940.2 (2)
C24—P1—C9—C8134.6 (2)C12—P1—C24—C29166.5 (2)
C18—P1—C9—C817.1 (2)C18—P1—C24—C2982.1 (2)
C8—C9—C10—O5166.1 (2)C29—C24—C25—C260.3 (4)
P1—C9—C10—O59.6 (3)P1—C24—C25—C26178.4 (2)
C8—C9—C10—C1113.1 (4)C24—C25—C26—C271.7 (5)
P1—C9—C10—C11171.2 (2)C25—C26—C27—C282.3 (5)
C9—P1—C12—C1710.7 (3)C26—C27—C28—C291.4 (5)
C24—P1—C12—C17111.6 (2)C27—C28—C29—C240.1 (5)
C18—P1—C12—C17135.4 (2)C25—C24—C29—C280.6 (4)
C9—P1—C12—C13164.6 (2)P1—C24—C29—C28179.4 (2)
C24—P1—C12—C1373.1 (2)
 

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