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In the title mol­ecule, C22H22N2O6, the planes of the two methoxy­carbonyl groups are oriented at angles of 5.19 (14) and 80.21 (9)° with respect to that of the indolizine ring. In the crystal structure, the mol­ecules are linked by weak inter­molecular C—H...O inter­actions to form centrosymmetric ring motifs.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806001851/lh6577sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806001851/lh6577Isup2.hkl
Contains datablock I

CCDC reference: 298494

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.060
  • wR factor = 0.147
  • Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.68 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.09 Ratio PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. CG1 .. 2.91 Ang.
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 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Version 1.07; Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Dimethyl 7-(N,N-dimethylamino)-3-(2-methoxybenzoyl)indolizine-1,2-dicarbxylate top
Crystal data top
C22H22N2O6F(000) = 1728
Mr = 410.42Dx = 1.334 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -c 2ycCell parameters from 2107 reflections
a = 28.878 (3) Åθ = 2.3–24.1°
b = 8.0015 (8) ŵ = 0.10 mm1
c = 18.7634 (18) ÅT = 293 K
β = 109.547 (2)°Prism, yellow
V = 4085.7 (7) Å30.28 × 0.18 × 0.15 mm
Z = 8
Data collection top
Siemens SMART CCD area-detector
diffractometer
2589 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Graphite monochromatorθmax = 25.0°, θmin = 2.3°
ω scansh = 3434
10194 measured reflectionsk = 99
3481 independent reflectionsl = 2219
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0619P)2 + 1.9395P]
where P = (Fo2 + 2Fc2)/3
3481 reflections(Δ/σ)max < 0.001
276 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.18 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
O100.08533 (8)0.9398 (3)0.12213 (12)0.0759 (7)
O110.03996 (7)0.7911 (3)0.06876 (12)0.0757 (6)
O130.06713 (7)0.5277 (2)0.06603 (12)0.0685 (6)
O140.04347 (7)0.7815 (3)0.08888 (12)0.0698 (6)
O160.22588 (7)0.6645 (3)0.23314 (11)0.0613 (6)
O260.16212 (7)0.3454 (2)0.20049 (12)0.0612 (5)
N40.19670 (7)0.8355 (2)0.09020 (11)0.0405 (5)
N230.27088 (8)1.0617 (3)0.03835 (13)0.0558 (6)
C10.12109 (9)0.8390 (3)0.00285 (14)0.0460 (6)
C20.11860 (9)0.7592 (3)0.06828 (14)0.0429 (6)
C30.16499 (9)0.7560 (3)0.12274 (14)0.0409 (6)
C50.24604 (9)0.8683 (3)0.12098 (15)0.0446 (6)
H50.26300.83900.17090.053*
C60.26985 (9)0.9424 (3)0.07918 (15)0.0473 (7)
H60.30340.96280.10100.057*
C70.24572 (9)0.9911 (3)0.00279 (15)0.0440 (6)
C80.19518 (9)0.9636 (3)0.02597 (14)0.0452 (6)
H80.17750.99790.07490.054*
C90.17081 (9)0.8858 (3)0.01728 (14)0.0408 (6)
C100.08188 (11)0.8648 (3)0.06857 (17)0.0547 (7)
C120.00310 (11)0.8125 (5)0.1338 (2)0.0940 (12)
H1210.01630.92240.13320.141*
H1220.02720.73050.13310.141*
H1230.00530.79870.17880.141*
C130.07400 (10)0.6741 (3)0.07391 (16)0.0515 (7)
C150.00197 (13)0.7083 (5)0.0918 (3)0.1095 (15)
H1510.01570.63660.04890.164*
H1520.02490.79560.09110.164*
H1530.00470.64440.13750.164*
C160.18214 (10)0.6784 (3)0.19584 (14)0.0445 (6)
C170.14474 (9)0.6150 (3)0.22905 (15)0.0475 (7)
C180.13726 (9)0.4444 (3)0.23395 (14)0.0480 (7)
C190.10650 (11)0.3867 (4)0.27173 (17)0.0639 (8)
H190.10140.27270.27520.077*
C200.08359 (13)0.5001 (5)0.3040 (2)0.0798 (10)
H200.06320.46140.32970.096*
C210.09018 (13)0.6684 (5)0.2990 (2)0.0845 (11)
H210.07440.74360.32090.101*
C220.12051 (11)0.7251 (4)0.26118 (18)0.0661 (8)
H220.12480.83950.25710.079*
C240.32345 (11)1.0900 (4)0.00766 (18)0.0632 (8)
H2410.33031.17410.03100.095*
H2420.33511.12680.04730.095*
H2430.33970.98800.01360.095*
C250.24560 (12)1.1156 (4)0.11553 (17)0.0672 (9)
H2510.23051.02090.14580.101*
H2520.26881.16550.13570.101*
H2530.22081.19600.11610.101*
C260.15248 (12)0.1713 (4)0.1954 (2)0.0890 (11)
H2610.15770.12710.24510.133*
H2620.17410.11690.17350.133*
H2630.11900.15210.16420.133*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O100.0678 (15)0.0895 (16)0.0600 (14)0.0046 (12)0.0075 (11)0.0161 (12)
O110.0417 (12)0.0998 (16)0.0728 (14)0.0074 (11)0.0021 (10)0.0006 (12)
O130.0542 (12)0.0562 (12)0.0920 (16)0.0129 (10)0.0203 (11)0.0090 (11)
O140.0490 (12)0.0707 (13)0.0996 (17)0.0049 (10)0.0381 (12)0.0178 (12)
O160.0468 (12)0.0803 (14)0.0551 (12)0.0072 (10)0.0148 (10)0.0149 (10)
O260.0577 (12)0.0464 (10)0.0820 (14)0.0020 (9)0.0268 (11)0.0004 (10)
N40.0379 (12)0.0421 (11)0.0413 (12)0.0027 (9)0.0132 (10)0.0030 (9)
N230.0532 (15)0.0650 (15)0.0562 (15)0.0031 (12)0.0274 (12)0.0067 (12)
C10.0404 (15)0.0457 (14)0.0495 (16)0.0031 (12)0.0117 (13)0.0038 (12)
C20.0398 (14)0.0409 (13)0.0512 (16)0.0013 (11)0.0194 (13)0.0083 (12)
C30.0389 (14)0.0413 (13)0.0445 (14)0.0035 (11)0.0164 (12)0.0043 (11)
C50.0417 (15)0.0475 (14)0.0427 (14)0.0047 (12)0.0115 (12)0.0024 (12)
C60.0383 (14)0.0511 (15)0.0540 (17)0.0059 (12)0.0176 (13)0.0012 (13)
C70.0489 (15)0.0384 (13)0.0503 (16)0.0025 (11)0.0240 (13)0.0033 (11)
C80.0514 (16)0.0439 (13)0.0418 (15)0.0061 (12)0.0176 (13)0.0003 (11)
C90.0440 (15)0.0386 (13)0.0401 (15)0.0022 (11)0.0146 (12)0.0033 (11)
C100.0511 (18)0.0510 (16)0.0575 (19)0.0045 (13)0.0123 (15)0.0030 (14)
C120.049 (2)0.108 (3)0.098 (3)0.0070 (19)0.0119 (19)0.011 (2)
C130.0424 (16)0.0512 (16)0.0595 (18)0.0036 (13)0.0151 (13)0.0081 (13)
C150.062 (2)0.118 (3)0.172 (4)0.023 (2)0.071 (3)0.032 (3)
C160.0432 (15)0.0447 (14)0.0467 (15)0.0064 (12)0.0164 (13)0.0056 (12)
C170.0447 (15)0.0530 (16)0.0455 (15)0.0069 (12)0.0159 (13)0.0022 (12)
C180.0421 (15)0.0562 (16)0.0434 (15)0.0059 (13)0.0112 (13)0.0010 (13)
C190.0580 (19)0.0699 (19)0.064 (2)0.0193 (16)0.0205 (16)0.0044 (16)
C200.077 (2)0.097 (3)0.084 (3)0.028 (2)0.052 (2)0.006 (2)
C210.089 (3)0.093 (3)0.100 (3)0.017 (2)0.069 (2)0.023 (2)
C220.073 (2)0.0586 (17)0.081 (2)0.0133 (15)0.0451 (18)0.0156 (16)
C240.064 (2)0.0625 (18)0.078 (2)0.0035 (15)0.0444 (18)0.0010 (16)
C250.077 (2)0.074 (2)0.061 (2)0.0003 (16)0.0371 (17)0.0104 (16)
C260.074 (2)0.0539 (19)0.137 (3)0.0056 (17)0.032 (2)0.010 (2)
Geometric parameters (Å, º) top
O10—C101.203 (3)C8—H80.9300
O11—C101.345 (3)C12—H1210.9600
O11—C121.432 (3)C12—H1220.9600
O13—C131.189 (3)C12—H1230.9600
O14—C131.327 (3)C15—H1510.9600
O14—C151.455 (4)C15—H1520.9600
O16—C161.227 (3)C15—H1530.9600
O26—C181.356 (3)C16—C171.504 (4)
O26—C261.417 (3)C17—C221.383 (4)
N4—C51.372 (3)C17—C181.390 (4)
N4—C91.381 (3)C18—C191.388 (4)
N4—C31.411 (3)C19—C201.377 (4)
N23—C71.349 (3)C19—H190.9300
N23—C241.450 (3)C20—C211.368 (5)
N23—C251.452 (4)C20—H200.9300
C1—C21.407 (3)C21—C221.376 (4)
C1—C91.420 (3)C21—H210.9300
C1—C101.451 (4)C22—H220.9300
C2—C31.387 (3)C24—H2410.9600
C2—C131.492 (4)C24—H2420.9600
C3—C161.434 (4)C24—H2430.9600
C5—C61.342 (3)C25—H2510.9600
C5—H50.9300C25—H2520.9600
C6—C71.422 (4)C25—H2530.9600
C6—H60.9300C26—H2610.9600
C7—C81.394 (4)C26—H2620.9600
C8—C91.387 (4)C26—H2630.9600
C10—O11—C12118.3 (3)O14—C15—H151109.5
C13—O14—C15114.8 (2)O14—C15—H152109.5
C18—O26—C26118.9 (2)H151—C15—H152109.5
C5—N4—C9120.2 (2)O14—C15—H153109.5
C5—N4—C3129.6 (2)H151—C15—H153109.5
C9—N4—C3110.21 (19)H152—C15—H153109.5
C7—N23—C24122.1 (2)O16—C16—C3123.0 (2)
C7—N23—C25120.5 (2)O16—C16—C17118.5 (2)
C24—N23—C25117.4 (2)C3—C16—C17118.4 (2)
C2—C1—C9107.3 (2)C22—C17—C18119.0 (3)
C2—C1—C10128.2 (2)C22—C17—C16120.3 (2)
C9—C1—C10124.4 (3)C18—C17—C16120.5 (2)
C3—C2—C1109.4 (2)O26—C18—C19124.8 (3)
C3—C2—C13125.7 (2)O26—C18—C17115.2 (2)
C1—C2—C13124.5 (2)C19—C18—C17120.0 (3)
C2—C3—N4106.2 (2)C20—C19—C18119.3 (3)
C2—C3—C16130.7 (2)C20—C19—H19120.3
N4—C3—C16122.9 (2)C18—C19—H19120.3
C6—C5—N4120.1 (2)C21—C20—C19121.3 (3)
C6—C5—H5120.0C21—C20—H20119.3
N4—C5—H5120.0C19—C20—H20119.3
C5—C6—C7122.4 (2)C20—C21—C22119.1 (3)
C5—C6—H6118.8C20—C21—H21120.4
C7—C6—H6118.8C22—C21—H21120.4
N23—C7—C8122.6 (2)C21—C22—C17121.2 (3)
N23—C7—C6121.0 (2)C21—C22—H22119.4
C8—C7—C6116.3 (2)C17—C22—H22119.4
C9—C8—C7121.0 (2)N23—C24—H241109.5
C9—C8—H8119.5N23—C24—H242109.5
C7—C8—H8119.5H241—C24—H242109.5
N4—C9—C8119.9 (2)N23—C24—H243109.5
N4—C9—C1106.8 (2)H241—C24—H243109.5
C8—C9—C1133.3 (2)H242—C24—H243109.5
O10—C10—O11122.8 (3)N23—C25—H251109.5
O10—C10—C1125.8 (3)N23—C25—H252109.5
O11—C10—C1111.3 (3)H251—C25—H252109.5
O11—C12—H121109.5N23—C25—H253109.5
O11—C12—H122109.5H251—C25—H253109.5
H121—C12—H122109.5H252—C25—H253109.5
O11—C12—H123109.5O26—C26—H261109.5
H121—C12—H123109.5O26—C26—H262109.5
H122—C12—H123109.5H261—C26—H262109.5
O13—C13—O14124.7 (3)O26—C26—H263109.5
O13—C13—C2123.6 (2)H261—C26—H263109.5
O14—C13—C2111.7 (2)H262—C26—H263109.5
C9—C1—C2—C30.3 (3)C12—O11—C10—O104.1 (4)
C10—C1—C2—C3177.7 (2)C12—O11—C10—C1176.7 (3)
C9—C1—C2—C13173.0 (2)C2—C1—C10—O10176.8 (3)
C10—C1—C2—C134.4 (4)C9—C1—C10—O106.2 (4)
C1—C2—C3—N40.0 (3)C2—C1—C10—O114.0 (4)
C13—C2—C3—N4173.2 (2)C9—C1—C10—O11172.9 (2)
C1—C2—C3—C16174.6 (2)C15—O14—C13—O132.8 (4)
C13—C2—C3—C161.4 (4)C15—O14—C13—C2177.4 (3)
C5—N4—C3—C2178.4 (2)C3—C2—C13—O1375.5 (4)
C9—N4—C3—C20.4 (3)C1—C2—C13—O1396.7 (3)
C5—N4—C3—C166.4 (4)C3—C2—C13—O14104.3 (3)
C9—N4—C3—C16174.8 (2)C1—C2—C13—O1483.5 (3)
C9—N4—C5—C63.1 (3)C2—C3—C16—O16168.4 (3)
C3—N4—C5—C6178.3 (2)N4—C3—C16—O165.5 (4)
N4—C5—C6—C70.5 (4)C2—C3—C16—C1713.2 (4)
C24—N23—C7—C8179.8 (2)N4—C3—C16—C17172.9 (2)
C25—N23—C7—C81.0 (4)O16—C16—C17—C22100.8 (3)
C24—N23—C7—C60.7 (4)C3—C16—C17—C2277.7 (3)
C25—N23—C7—C6178.1 (2)O16—C16—C17—C1873.4 (3)
C5—C6—C7—N23178.4 (2)C3—C16—C17—C18108.1 (3)
C5—C6—C7—C82.5 (4)C26—O26—C18—C197.5 (4)
N23—C7—C8—C9178.0 (2)C26—O26—C18—C17173.1 (3)
C6—C7—C8—C92.9 (3)C22—C17—C18—O26179.5 (2)
C5—N4—C9—C82.6 (3)C16—C17—C18—O266.2 (4)
C3—N4—C9—C8178.5 (2)C22—C17—C18—C191.0 (4)
C5—N4—C9—C1178.3 (2)C16—C17—C18—C19173.3 (2)
C3—N4—C9—C10.6 (3)O26—C18—C19—C20179.4 (3)
C7—C8—C9—N40.5 (3)C17—C18—C19—C200.1 (4)
C7—C8—C9—C1178.4 (2)C18—C19—C20—C210.6 (5)
C2—C1—C9—N40.6 (3)C19—C20—C21—C220.3 (6)
C10—C1—C9—N4178.0 (2)C20—C21—C22—C170.8 (5)
C2—C1—C9—C8178.4 (3)C18—C17—C22—C211.4 (5)
C10—C1—C9—C80.9 (4)C16—C17—C22—C21172.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H151···O13i0.962.543.486 (5)169
C6—H6···Cg1ii0.932.923.742 (3)149
Symmetry codes: (i) x, y+1, z; (ii) x, y, z1/2.
 

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