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In the title compound, C30H25NO4, the indolizine moiety is not completely planar, the six-membered ring being distorted towards an envelope conformation. The benzoyl and phenyl substituents are each almost planar. The crystal structure is stabilized by dipole-dipole and van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803023195/cv6243sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803023195/cv6243Isup2.hkl
Contains datablock I

CCDC reference: 227868

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.044
  • wR factor = 0.143
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.789 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.77 Ratio PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C30 H25 N O4
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 1 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 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

1,3-Dibenzoyl-5,8-dimethoxy-2-phenyl-5,8-dihydroindolizine top
Crystal data top
C30H25NO4Dx = 1.281 Mg m3
Mr = 463.51Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 7716 reflections
a = 12.8820 (6) Åθ = 2.4–28.3°
b = 12.1160 (5) ŵ = 0.09 mm1
c = 30.7987 (13) ÅT = 293 K
V = 4807.0 (4) Å3Block, colourless
Z = 80.60 × 0.56 × 0.54 mm
F(000) = 1952
Data collection top
Siemens SMART CCD area-detector
diffractometer
5925 independent reflections
Radiation source: fine-focus sealed tube4883 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 2.4°
ω scansh = 1710
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1615
Tmin = 0.951, Tmax = 0.956l = 3540
28443 measured 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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 0.79 w = 1/[σ2(Fo2) + (0.1093P)2 + 2.1064P]
where P = (Fo2 + 2Fc2)/3
5925 reflections(Δ/σ)max < 0.001
382 parametersΔρmax = 0.27 e Å3
0 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 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
O10.05967 (7)0.23263 (9)0.28804 (3)0.0439 (2)
O20.30455 (7)0.04121 (8)0.27863 (4)0.0444 (2)
O30.39286 (8)0.24816 (9)0.33925 (4)0.0520 (3)
O40.06556 (9)0.19108 (10)0.41633 (4)0.0543 (3)
N10.18939 (8)0.15765 (8)0.31750 (3)0.0303 (2)
C10.16152 (9)0.14574 (10)0.38935 (4)0.0315 (2)
C20.23749 (9)0.15821 (10)0.35777 (4)0.0311 (2)
C30.24492 (10)0.13968 (10)0.27646 (4)0.0337 (3)
H30.2959 (12)0.1985 (13)0.2730 (5)0.035 (4)*
C40.17053 (12)0.13960 (12)0.23912 (4)0.0422 (3)
C50.06838 (11)0.14112 (12)0.24264 (4)0.0421 (3)
C60.01161 (10)0.14183 (11)0.28517 (4)0.0345 (3)
C70.08504 (8)0.14010 (9)0.32304 (4)0.0287 (2)
C80.06492 (9)0.13496 (10)0.36713 (4)0.0302 (2)
C90.04017 (9)0.12887 (10)0.38725 (4)0.0328 (2)
C100.11280 (9)0.04131 (10)0.37151 (4)0.0313 (2)
C110.07496 (10)0.05860 (11)0.35575 (5)0.0395 (3)
C120.14303 (13)0.14157 (13)0.34376 (5)0.0491 (3)
C130.24883 (13)0.12467 (14)0.34643 (5)0.0502 (4)
C140.28716 (11)0.02524 (14)0.36184 (5)0.0474 (3)
C150.21972 (10)0.05748 (12)0.37495 (4)0.0384 (3)
C160.17746 (10)0.14214 (12)0.43686 (4)0.0375 (3)
C170.23827 (12)0.22114 (14)0.45786 (5)0.0476 (3)
C180.25442 (16)0.2141 (2)0.50272 (6)0.0681 (6)
C190.20995 (18)0.1307 (2)0.52623 (6)0.0794 (7)
H19A0.22060.12690.55610.095*
C200.14976 (17)0.0527 (2)0.50602 (6)0.0755 (6)
H20A0.12010.00390.52220.091*
C210.13292 (14)0.05794 (16)0.46146 (5)0.0554 (4)
C220.35064 (9)0.17835 (10)0.36178 (4)0.0346 (3)
C230.41095 (9)0.11140 (11)0.39338 (4)0.0363 (3)
C240.38820 (12)0.00089 (13)0.39995 (5)0.0468 (3)
C250.45009 (14)0.06275 (16)0.42718 (7)0.0606 (4)
C260.53163 (13)0.01439 (18)0.44887 (6)0.0655 (5)
H26A0.57240.05660.46740.079*
C270.55329 (13)0.0953 (2)0.44335 (6)0.0635 (5)
C280.49457 (11)0.15898 (15)0.41507 (5)0.0482 (3)
C290.01103 (14)0.33777 (14)0.28699 (7)0.0585 (4)
H29A0.06310.39450.28760.088*
H29B0.03350.34550.31180.088*
H29C0.02930.34440.26090.088*
C300.24484 (14)0.05671 (13)0.28423 (7)0.0600 (4)
H30A0.29040.11790.28960.090*
H30B0.19870.04770.30850.090*
H30C0.20510.07060.25840.090*
H110.0042 (14)0.0701 (14)0.3541 (5)0.046 (4)*
H60.0324 (13)0.0776 (14)0.2859 (5)0.039 (4)*
H170.2693 (14)0.2799 (15)0.4410 (6)0.047 (4)*
H40.2060 (14)0.1345 (15)0.2113 (6)0.057 (5)*
H130.2953 (15)0.1832 (17)0.3376 (6)0.062 (5)*
H280.5090 (15)0.2391 (16)0.4093 (6)0.058 (5)*
H150.2444 (13)0.1271 (14)0.3863 (5)0.042 (4)*
H210.0936 (16)0.0012 (17)0.4466 (6)0.062 (5)*
H240.3288 (15)0.0302 (16)0.3849 (6)0.057 (5)*
H50.0256 (14)0.1404 (14)0.2174 (6)0.051 (5)*
H140.3584 (16)0.0134 (16)0.3636 (6)0.060 (5)*
H270.608 (2)0.132 (2)0.4594 (8)0.097 (8)*
H120.1149 (16)0.2147 (18)0.3342 (7)0.064 (5)*
H180.2974 (19)0.269 (2)0.5146 (8)0.083 (7)*
H250.4393 (18)0.141 (2)0.4304 (8)0.085 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0287 (4)0.0545 (6)0.0485 (5)0.0077 (4)0.0035 (4)0.0006 (4)
O20.0330 (5)0.0423 (5)0.0580 (6)0.0068 (4)0.0042 (4)0.0013 (4)
O30.0399 (5)0.0570 (6)0.0591 (6)0.0165 (5)0.0047 (5)0.0187 (5)
O40.0433 (6)0.0602 (7)0.0593 (7)0.0081 (5)0.0153 (5)0.0260 (5)
N10.0263 (5)0.0354 (5)0.0292 (5)0.0010 (4)0.0005 (4)0.0030 (4)
C10.0289 (5)0.0349 (6)0.0307 (5)0.0021 (4)0.0013 (4)0.0016 (4)
C20.0276 (5)0.0342 (6)0.0316 (5)0.0019 (4)0.0023 (4)0.0028 (4)
C30.0317 (6)0.0350 (6)0.0344 (6)0.0011 (5)0.0065 (5)0.0023 (4)
C40.0481 (7)0.0496 (7)0.0289 (6)0.0081 (6)0.0048 (5)0.0017 (5)
C50.0457 (7)0.0519 (7)0.0287 (6)0.0070 (6)0.0054 (5)0.0003 (5)
C60.0306 (6)0.0405 (6)0.0323 (6)0.0000 (5)0.0047 (5)0.0001 (5)
C70.0243 (5)0.0326 (5)0.0292 (5)0.0005 (4)0.0004 (4)0.0004 (4)
C80.0264 (5)0.0339 (5)0.0304 (5)0.0014 (4)0.0005 (4)0.0000 (4)
C90.0288 (5)0.0369 (6)0.0327 (6)0.0001 (4)0.0028 (4)0.0007 (4)
C100.0288 (5)0.0354 (6)0.0298 (5)0.0019 (4)0.0016 (4)0.0024 (4)
C110.0361 (6)0.0383 (6)0.0441 (7)0.0002 (5)0.0010 (5)0.0026 (5)
C120.0549 (9)0.0402 (7)0.0521 (8)0.0053 (6)0.0045 (7)0.0061 (6)
C130.0492 (8)0.0525 (8)0.0488 (8)0.0171 (7)0.0115 (7)0.0020 (6)
C140.0310 (6)0.0647 (9)0.0465 (7)0.0077 (6)0.0039 (6)0.0065 (7)
C150.0307 (6)0.0460 (7)0.0384 (6)0.0004 (5)0.0023 (5)0.0026 (5)
C160.0319 (6)0.0506 (7)0.0299 (6)0.0059 (5)0.0013 (5)0.0011 (5)
C170.0425 (7)0.0590 (9)0.0413 (7)0.0075 (7)0.0085 (6)0.0106 (6)
C180.0626 (10)0.0948 (15)0.0470 (9)0.0235 (10)0.0188 (8)0.0245 (10)
C190.0802 (14)0.1261 (19)0.0318 (8)0.0373 (13)0.0073 (8)0.0049 (10)
C200.0767 (13)0.1067 (17)0.0432 (9)0.0175 (12)0.0101 (9)0.0281 (10)
C210.0540 (9)0.0706 (11)0.0415 (8)0.0011 (8)0.0022 (7)0.0157 (7)
C220.0280 (6)0.0374 (6)0.0383 (6)0.0039 (5)0.0012 (5)0.0019 (5)
C230.0248 (5)0.0441 (7)0.0401 (6)0.0002 (5)0.0002 (5)0.0021 (5)
C240.0377 (7)0.0436 (7)0.0590 (9)0.0008 (6)0.0017 (6)0.0038 (6)
C250.0512 (9)0.0545 (9)0.0760 (12)0.0132 (7)0.0063 (8)0.0194 (8)
C260.0420 (8)0.0917 (14)0.0626 (10)0.0184 (9)0.0007 (7)0.0269 (9)
C270.0370 (8)0.0968 (14)0.0565 (9)0.0031 (8)0.0129 (7)0.0082 (10)
C280.0342 (7)0.0596 (9)0.0509 (8)0.0084 (6)0.0070 (6)0.0029 (6)
C290.0529 (9)0.0463 (8)0.0762 (11)0.0123 (7)0.0031 (8)0.0039 (8)
C300.0535 (9)0.0358 (7)0.0907 (13)0.0040 (6)0.0099 (9)0.0013 (7)
Geometric parameters (Å, º) top
O1—C291.420 (2)C14—C151.386 (2)
O1—C61.4357 (16)C14—H140.93 (2)
O2—C31.4205 (15)C15—H150.966 (17)
O2—C301.4245 (19)C16—C211.394 (2)
O3—C221.2219 (16)C16—C171.396 (2)
O4—C91.2154 (15)C17—C181.400 (2)
N1—C71.3717 (14)C17—H170.968 (18)
N1—C21.3865 (15)C18—C191.368 (4)
N1—C31.4687 (15)C18—H180.94 (3)
C1—C21.3879 (16)C19—C201.372 (4)
C1—C81.4260 (16)C19—H19A0.9300
C1—C161.4784 (17)C20—C211.391 (2)
C2—C221.4831 (16)C20—H20A0.9300
C3—C41.4968 (19)C21—H210.99 (2)
C3—H30.975 (16)C22—C231.4862 (18)
C4—C51.320 (2)C23—C241.385 (2)
C4—H40.973 (19)C23—C281.3924 (19)
C5—C61.5002 (18)C24—C251.390 (2)
C5—H50.954 (18)C24—H240.97 (2)
C6—C71.5019 (16)C25—C261.376 (3)
C6—H60.963 (17)C25—H250.96 (2)
C7—C81.3839 (16)C26—C271.368 (3)
C8—C91.4907 (16)C26—H26A0.9300
C9—C101.4952 (17)C27—C281.388 (2)
C10—C111.3923 (18)C27—H270.97 (3)
C10—C151.3953 (17)C28—H281.005 (19)
C11—C121.384 (2)C29—H29A0.9600
C11—H111.031 (18)C29—H29B0.9600
C12—C131.381 (2)C29—H29C0.9600
C12—H121.00 (2)C30—H30A0.9600
C13—C141.386 (2)C30—H30B0.9600
C13—H130.97 (2)C30—H30C0.9600
C29—O1—C6113.82 (10)C14—C15—H15122.0 (10)
C3—O2—C30114.41 (11)C10—C15—H15118.4 (10)
C7—N1—C2109.11 (9)C21—C16—C17118.76 (14)
C7—N1—C3124.16 (10)C21—C16—C1120.15 (13)
C2—N1—C3123.57 (10)C17—C16—C1121.08 (13)
C2—C1—C8106.80 (10)C16—C17—C18119.91 (18)
C2—C1—C16126.79 (11)C16—C17—H17119.2 (10)
C8—C1—C16126.40 (11)C18—C17—H17120.9 (10)
N1—C2—C1108.13 (10)C19—C18—C17120.3 (2)
N1—C2—C22120.96 (10)C19—C18—H18124.4 (15)
C1—C2—C22130.74 (11)C17—C18—H18115.2 (16)
O2—C3—N1110.33 (10)C18—C19—C20120.32 (16)
O2—C3—C4112.45 (11)C18—C19—H19A119.8
N1—C3—C4110.45 (10)C20—C19—H19A119.8
O2—C3—H3104.8 (9)C19—C20—C21120.32 (19)
N1—C3—H3108.2 (9)C19—C20—H20A119.8
C4—C3—H3110.4 (9)C21—C20—H20A119.8
C5—C4—C3125.11 (12)C20—C21—C16120.34 (19)
C5—C4—H4122.7 (11)C20—C21—H21120.2 (12)
C3—C4—H4112.1 (11)C16—C21—H21119.4 (12)
C4—C5—C6123.88 (12)O3—C22—C2120.28 (11)
C4—C5—H5120.6 (11)O3—C22—C23121.13 (11)
C6—C5—H5115.6 (11)C2—C22—C23118.59 (10)
O1—C6—C5111.72 (10)C24—C23—C28119.58 (13)
O1—C6—C7111.44 (10)C24—C23—C22120.83 (12)
C5—C6—C7111.77 (11)C28—C23—C22119.51 (13)
O1—C6—H6104.0 (10)C23—C24—C25120.18 (15)
C5—C6—H6107.6 (9)C23—C24—H24118.1 (11)
C7—C6—H6109.9 (9)C25—C24—H24121.7 (11)
N1—C7—C8108.21 (10)C26—C25—C24119.63 (17)
N1—C7—C6121.23 (10)C26—C25—H25118.6 (15)
C8—C7—C6130.15 (10)C24—C25—H25121.7 (15)
C7—C8—C1107.66 (10)C27—C26—C25120.60 (16)
C7—C8—C9125.46 (10)C27—C26—H26A119.7
C1—C8—C9126.70 (11)C25—C26—H26A119.7
O4—C9—C8121.33 (11)C26—C27—C28120.44 (17)
O4—C9—C10120.70 (11)C26—C27—H27122.0 (16)
C8—C9—C10117.94 (10)C28—C27—H27117.5 (16)
C11—C10—C15119.61 (12)C27—C28—C23119.51 (16)
C11—C10—C9120.72 (11)C27—C28—H28123.3 (11)
C15—C10—C9119.57 (11)C23—C28—H28117.2 (11)
C12—C11—C10120.18 (13)O1—C29—H29A109.5
C12—C11—H11121.1 (9)O1—C29—H29B109.5
C10—C11—H11118.7 (9)H29A—C29—H29B109.5
C13—C12—C11120.11 (15)O1—C29—H29C109.5
C13—C12—H12120.4 (12)H29A—C29—H29C109.5
C11—C12—H12119.5 (12)H29B—C29—H29C109.5
C12—C13—C14120.07 (14)O2—C30—H30A109.5
C12—C13—H13119.1 (12)O2—C30—H30B109.5
C14—C13—H13120.9 (12)H30A—C30—H30B109.5
C13—C14—C15120.32 (13)O2—C30—H30C109.5
C13—C14—H14120.4 (12)H30A—C30—H30C109.5
C15—C14—H14119.3 (12)H30B—C30—H30C109.5
C14—C15—C10119.67 (13)
C7—N1—C2—C12.68 (13)O4—C9—C10—C11148.39 (14)
C3—N1—C2—C1163.27 (11)C8—C9—C10—C1129.77 (17)
C7—N1—C2—C22178.45 (11)O4—C9—C10—C1527.96 (19)
C3—N1—C2—C2220.96 (17)C8—C9—C10—C15153.89 (11)
C8—C1—C2—N11.28 (13)C15—C10—C11—C120.3 (2)
C16—C1—C2—N1179.78 (12)C9—C10—C11—C12176.05 (13)
C8—C1—C2—C22176.49 (12)C10—C11—C12—C131.5 (2)
C16—C1—C2—C224.6 (2)C11—C12—C13—C141.1 (2)
C30—O2—C3—N163.02 (15)C12—C13—C14—C150.5 (2)
C30—O2—C3—C460.77 (16)C13—C14—C15—C101.7 (2)
C7—N1—C3—O2104.85 (13)C11—C10—C15—C141.28 (19)
C2—N1—C3—O252.85 (15)C9—C10—C15—C14177.67 (12)
C7—N1—C3—C420.09 (16)C2—C1—C16—C21130.50 (15)
C2—N1—C3—C4177.79 (11)C8—C1—C16—C2148.24 (19)
O2—C3—C4—C5115.64 (16)C2—C1—C16—C1748.44 (19)
N1—C3—C4—C58.1 (2)C8—C1—C16—C17132.81 (14)
C3—C4—C5—C60.7 (2)C21—C16—C17—C180.7 (2)
C29—O1—C6—C563.49 (15)C1—C16—C17—C18178.25 (14)
C29—O1—C6—C762.34 (15)C16—C17—C18—C190.7 (3)
C4—C5—C6—O1125.40 (15)C17—C18—C19—C200.5 (3)
C4—C5—C6—C70.2 (2)C18—C19—C20—C210.3 (3)
C2—N1—C7—C83.03 (13)C19—C20—C21—C160.3 (3)
C3—N1—C7—C8163.48 (10)C17—C16—C21—C200.5 (2)
C2—N1—C7—C6176.41 (10)C1—C16—C21—C20178.45 (16)
C3—N1—C7—C623.13 (17)N1—C2—C22—O340.25 (19)
O1—C6—C7—N1114.19 (12)C1—C2—C22—O3134.44 (15)
C5—C6—C7—N111.61 (16)N1—C2—C22—C23139.27 (12)
O1—C6—C7—C857.58 (17)C1—C2—C22—C2346.04 (19)
C5—C6—C7—C8176.62 (12)O3—C22—C23—C24142.25 (15)
N1—C7—C8—C12.19 (13)C2—C22—C23—C2437.27 (18)
C6—C7—C8—C1174.79 (12)O3—C22—C23—C2834.6 (2)
N1—C7—C8—C9173.10 (11)C2—C22—C23—C28145.89 (13)
C6—C7—C8—C90.5 (2)C28—C23—C24—C251.6 (2)
C2—C1—C8—C70.55 (13)C22—C23—C24—C25175.21 (14)
C16—C1—C8—C7178.40 (12)C23—C24—C25—C262.5 (3)
C2—C1—C8—C9174.67 (11)C24—C25—C26—C271.0 (3)
C16—C1—C8—C96.4 (2)C25—C26—C27—C281.3 (3)
C7—C8—C9—O4129.64 (15)C26—C27—C28—C232.2 (3)
C1—C8—C9—O444.76 (19)C24—C23—C28—C270.7 (2)
C7—C8—C9—C1052.22 (17)C22—C23—C28—C27177.59 (15)
C1—C8—C9—C10133.38 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O30.98 (2)2.47 (2)3.017 (2)115 (1)
C30—H30B···N10.962.512.882 (2)103
 

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