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In the title compound, C21H19BrN2O5, the planes of the two methoxy­carbonyl moieties are oriented at angles of 7.70 (6) and 69.09 (6)° with respect to that of the indolizine ring. In the solid state, the mol­ecules are held together by weak intermolecular C—H...O and C—H...Br interactions which form chain and centrosymmetric ring motifs.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804006993/cv6286sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804006993/cv6286Isup2.hkl
Contains datablock I

CCDC reference: 238833

Key indicators

  • Single-crystal X-ray study
  • T = 160 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.038
  • wR factor = 0.101
  • Data-to-parameter ratio = 21.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN and SCALEPACK (Otwinowski & Minor, 1997); 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 3-(4-bromobenzoyl)-7-(dimethylamino)indolizine-1,2-dicarboxylate top
Crystal data top
C21H19BrN2O5Z = 2
Mr = 459.29F(000) = 468
Triclinic, P1Dx = 1.570 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.5238 (2) ÅCell parameters from 29442 reflections
b = 10.2817 (2) Åθ = 2.0–30.0°
c = 13.8084 (2) ŵ = 2.15 mm1
α = 69.467 (1)°T = 160 K
β = 79.837 (1)°Prism, yellow
γ = 77.741 (1)°0.30 × 0.23 × 0.20 mm
V = 971.42 (3) Å3
Data collection top
Nonius KappaCCD
diffractometer
5684 independent reflections
Radiation source: Nonius FR590 sealed-tube generator4679 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromatorRint = 0.068
Detector resolution: 9 pixels mm-1θmax = 30.0°, θmin = 2.1°
φ and ω scans with κ offsetsh = 1010
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 1414
Tmin = 0.542, Tmax = 0.641l = 1918
25900 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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0525P)2 + 0.3259P]
where P = (Fo2 + 2Fc2)/3
5684 reflections(Δ/σ)max = 0.001
266 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.66 e Å3
Special details top

Experimental. Solvent used: ethyl acetate Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.520 (1) Frames collected: 593 Seconds exposure per frame: 18 Degrees rotation per frame: 1.2 Crystal-Detector distance (mm): 30.0

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
Br0.58377 (3)0.051668 (19)0.373158 (14)0.03668 (8)
O100.09686 (19)0.99154 (14)0.31954 (10)0.0293 (3)
O110.1975 (2)0.77072 (14)0.41945 (10)0.0312 (3)
O120.51632 (19)0.51669 (15)0.37150 (10)0.0317 (3)
O130.21565 (18)0.50813 (13)0.38664 (10)0.0276 (3)
O140.61471 (18)0.60190 (14)0.02307 (10)0.0277 (3)
N40.3463 (2)0.82034 (15)0.07670 (11)0.0202 (3)
N210.1129 (2)1.22963 (16)0.07832 (12)0.0284 (3)
C10.2424 (2)0.81898 (18)0.24074 (13)0.0210 (3)
C20.3326 (2)0.68335 (18)0.24416 (13)0.0209 (3)
C30.3976 (2)0.68229 (17)0.14341 (13)0.0210 (3)
C50.3770 (2)0.87474 (19)0.02974 (13)0.0230 (3)
H50.44970.81770.06800.028*
C60.3045 (2)1.00881 (19)0.08045 (14)0.0247 (3)
H60.32771.04470.15410.030*
C70.1933 (2)1.09806 (18)0.02550 (13)0.0228 (3)
C80.1706 (2)1.04302 (18)0.08353 (13)0.0223 (3)
H80.10301.10020.12300.027*
C90.2470 (2)0.90457 (18)0.13394 (13)0.0206 (3)
C100.1700 (2)0.87137 (18)0.32741 (13)0.0228 (3)
C110.1380 (4)0.8130 (2)0.51078 (15)0.0400 (5)
H1110.20330.88770.50730.060*
H1120.16430.73200.57310.060*
H1130.00610.84790.51400.060*
C120.3685 (2)0.56121 (18)0.34096 (13)0.0226 (3)
C130.2368 (3)0.3929 (2)0.48331 (16)0.0387 (5)
H1310.31490.31090.46900.058*
H1320.11650.36870.51640.058*
H1330.29340.42110.53000.058*
C140.5185 (2)0.57440 (18)0.10753 (13)0.0221 (3)
C150.5284 (2)0.42445 (18)0.17739 (13)0.0222 (3)
C160.3726 (3)0.36162 (19)0.21736 (14)0.0256 (3)
H160.25510.41640.20470.031*
C170.3874 (3)0.21930 (19)0.27563 (15)0.0273 (4)
H170.28160.17570.30210.033*
C180.5603 (3)0.14307 (19)0.29405 (14)0.0273 (4)
C190.7172 (3)0.2029 (2)0.25631 (14)0.0277 (4)
H190.83430.14850.27080.033*
C200.6999 (3)0.34424 (19)0.19684 (14)0.0259 (3)
H200.80640.38670.16910.031*
C220.1458 (3)1.2877 (2)0.19118 (14)0.0312 (4)
H2210.27601.29400.21180.047*
H2220.07301.38190.21510.047*
H2230.11051.22640.22270.047*
C230.0005 (3)1.3181 (2)0.02136 (15)0.0301 (4)
H2310.09531.26830.02550.045*
H2320.05621.40550.07050.045*
H2330.07691.34040.01940.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.05351 (15)0.02046 (11)0.02760 (11)0.00215 (8)0.00390 (8)0.00248 (7)
O100.0333 (7)0.0256 (7)0.0278 (7)0.0020 (5)0.0040 (5)0.0110 (5)
O110.0501 (8)0.0241 (7)0.0180 (6)0.0030 (6)0.0023 (5)0.0076 (5)
O120.0313 (7)0.0354 (8)0.0247 (6)0.0007 (6)0.0081 (5)0.0063 (6)
O130.0330 (7)0.0219 (6)0.0239 (6)0.0062 (5)0.0022 (5)0.0020 (5)
O140.0303 (7)0.0248 (6)0.0253 (6)0.0035 (5)0.0015 (5)0.0078 (5)
N40.0236 (7)0.0179 (7)0.0189 (6)0.0030 (5)0.0040 (5)0.0053 (5)
N210.0372 (9)0.0207 (7)0.0230 (7)0.0014 (6)0.0061 (6)0.0024 (6)
C10.0236 (8)0.0195 (8)0.0190 (7)0.0032 (6)0.0034 (6)0.0051 (6)
C20.0215 (8)0.0206 (8)0.0199 (7)0.0034 (6)0.0038 (6)0.0053 (6)
C30.0241 (8)0.0180 (7)0.0206 (8)0.0035 (6)0.0040 (6)0.0052 (6)
C50.0273 (9)0.0239 (8)0.0185 (7)0.0046 (7)0.0019 (6)0.0078 (6)
C60.0284 (9)0.0247 (8)0.0205 (8)0.0052 (7)0.0030 (6)0.0060 (6)
C70.0254 (8)0.0196 (8)0.0233 (8)0.0051 (6)0.0055 (6)0.0047 (6)
C80.0242 (8)0.0210 (8)0.0217 (8)0.0027 (6)0.0035 (6)0.0072 (6)
C90.0223 (8)0.0202 (8)0.0198 (7)0.0041 (6)0.0022 (6)0.0070 (6)
C100.0232 (8)0.0231 (8)0.0231 (8)0.0049 (7)0.0026 (6)0.0080 (6)
C110.0641 (15)0.0358 (11)0.0206 (9)0.0095 (10)0.0018 (9)0.0121 (8)
C120.0279 (9)0.0201 (8)0.0195 (8)0.0016 (6)0.0028 (6)0.0074 (6)
C130.0524 (13)0.0293 (10)0.0261 (9)0.0109 (9)0.0007 (8)0.0018 (8)
C140.0219 (8)0.0227 (8)0.0236 (8)0.0032 (6)0.0050 (6)0.0090 (6)
C150.0254 (8)0.0211 (8)0.0208 (8)0.0007 (6)0.0030 (6)0.0092 (6)
C160.0268 (9)0.0226 (8)0.0269 (9)0.0009 (7)0.0055 (7)0.0081 (7)
C170.0312 (10)0.0227 (9)0.0269 (9)0.0045 (7)0.0031 (7)0.0068 (7)
C180.0412 (11)0.0184 (8)0.0200 (8)0.0011 (7)0.0045 (7)0.0065 (6)
C190.0290 (9)0.0263 (9)0.0255 (9)0.0053 (7)0.0058 (7)0.0100 (7)
C200.0250 (9)0.0256 (9)0.0264 (8)0.0000 (7)0.0029 (6)0.0097 (7)
C220.0360 (10)0.0286 (9)0.0239 (9)0.0050 (8)0.0067 (7)0.0009 (7)
C230.0327 (10)0.0220 (8)0.0324 (10)0.0002 (7)0.0066 (7)0.0062 (7)
Geometric parameters (Å, º) top
Br—C181.9019 (18)C8—C91.393 (2)
O10—C101.216 (2)C8—H80.9500
O11—C101.345 (2)C11—H1110.9800
O11—C111.443 (2)C11—H1120.9800
O12—C121.199 (2)C11—H1130.9800
O13—C121.337 (2)C13—H1310.9800
O13—C131.448 (2)C13—H1320.9800
O14—C141.234 (2)C13—H1330.9800
N4—C51.373 (2)C14—C151.499 (2)
N4—C91.389 (2)C15—C201.390 (3)
N4—C31.410 (2)C15—C161.393 (3)
N21—C71.358 (2)C16—C171.392 (3)
N21—C231.450 (2)C16—H160.9500
N21—C221.456 (2)C17—C181.384 (3)
C1—C21.404 (2)C17—H170.9500
C1—C91.426 (2)C18—C191.383 (3)
C1—C101.455 (2)C19—C201.387 (3)
C2—C31.394 (2)C19—H190.9500
C2—C121.497 (2)C20—H200.9500
C3—C141.450 (2)C22—H2210.9800
C5—C61.351 (3)C22—H2220.9800
C5—H50.9500C22—H2230.9800
C6—C71.434 (3)C23—H2310.9800
C6—H60.9500C23—H2320.9800
C7—C81.403 (2)C23—H2330.9800
C10—O11—C11116.29 (15)O12—C12—C2123.77 (16)
C12—O13—C13114.59 (15)O13—C12—C2111.02 (15)
C5—N4—C9120.26 (14)O13—C13—H131109.5
C5—N4—C3129.56 (15)O13—C13—H132109.5
C9—N4—C3110.15 (13)H131—C13—H132109.5
C7—N21—C23119.66 (15)O13—C13—H133109.5
C7—N21—C22121.45 (16)H131—C13—H133109.5
C23—N21—C22118.79 (16)H132—C13—H133109.5
C2—C1—C9107.35 (14)O14—C14—C3122.50 (16)
C2—C1—C10128.19 (15)O14—C14—C15119.31 (15)
C9—C1—C10124.25 (15)C3—C14—C15118.17 (15)
C3—C2—C1109.49 (15)C20—C15—C16119.52 (16)
C3—C2—C12124.69 (15)C20—C15—C14118.38 (16)
C1—C2—C12125.63 (15)C16—C15—C14121.96 (15)
C2—C3—N4106.30 (14)C17—C16—C15120.57 (17)
C2—C3—C14130.27 (16)C17—C16—H16119.7
N4—C3—C14122.78 (15)C15—C16—H16119.7
C6—C5—N4120.52 (16)C18—C17—C16118.27 (17)
C6—C5—H5119.7C18—C17—H17120.9
N4—C5—H5119.7C16—C17—H17120.9
C5—C6—C7121.43 (16)C19—C18—C17122.44 (17)
C5—C6—H6119.3C19—C18—Br118.59 (14)
C7—C6—H6119.3C17—C18—Br118.97 (14)
N21—C7—C8122.24 (16)C18—C19—C20118.45 (17)
N21—C7—C6120.48 (15)C18—C19—H19120.8
C8—C7—C6117.27 (16)C20—C19—H19120.8
C9—C8—C7120.09 (16)C19—C20—C15120.73 (17)
C9—C8—H8120.0C19—C20—H20119.6
C7—C8—H8120.0C15—C20—H20119.6
N4—C9—C8120.27 (15)N21—C22—H221109.5
N4—C9—C1106.64 (14)N21—C22—H222109.5
C8—C9—C1133.05 (16)H221—C22—H222109.5
O10—C10—O11123.07 (16)N21—C22—H223109.5
O10—C10—C1125.27 (16)H221—C22—H223109.5
O11—C10—C1111.64 (15)H222—C22—H223109.5
O11—C11—H111109.5N21—C23—H231109.5
O11—C11—H112109.5N21—C23—H232109.5
H111—C11—H112109.5H231—C23—H232109.5
O11—C11—H113109.5N21—C23—H233109.5
H111—C11—H113109.5H231—C23—H233109.5
H112—C11—H113109.5H232—C23—H233109.5
O12—C12—O13125.19 (16)
C9—C1—C2—C31.59 (19)C10—C1—C9—C89.8 (3)
C10—C1—C2—C3173.26 (17)C11—O11—C10—O101.1 (3)
C9—C1—C2—C12176.65 (16)C11—O11—C10—C1177.40 (17)
C10—C1—C2—C121.8 (3)C2—C1—C10—O10178.06 (17)
C1—C2—C3—N40.04 (19)C9—C1—C10—O104.0 (3)
C12—C2—C3—N4175.08 (15)C2—C1—C10—O110.4 (3)
C1—C2—C3—C14170.81 (17)C9—C1—C10—O11174.47 (16)
C12—C2—C3—C144.3 (3)C13—O13—C12—O123.5 (3)
C5—N4—C3—C2179.87 (16)C13—O13—C12—C2177.64 (15)
C9—N4—C3—C21.73 (18)C3—C2—C12—O1268.1 (2)
C5—N4—C3—C148.5 (3)C1—C2—C12—O12106.3 (2)
C9—N4—C3—C14173.36 (15)C3—C2—C12—O13110.77 (19)
C9—N4—C5—C62.9 (2)C1—C2—C12—O1374.9 (2)
C3—N4—C5—C6175.11 (17)C2—C3—C14—O14153.73 (18)
N4—C5—C6—C70.3 (3)N4—C3—C14—O1415.7 (3)
C23—N21—C7—C80.5 (3)C2—C3—C14—C1525.1 (3)
C22—N21—C7—C8176.70 (17)N4—C3—C14—C15165.49 (15)
C23—N21—C7—C6179.80 (17)O14—C14—C15—C2048.6 (2)
C22—N21—C7—C64.0 (3)C3—C14—C15—C20130.23 (17)
C5—C6—C7—N21176.09 (17)O14—C14—C15—C16127.20 (18)
C5—C6—C7—C83.2 (3)C3—C14—C15—C1654.0 (2)
N21—C7—C8—C9176.23 (16)C20—C15—C16—C170.6 (3)
C6—C7—C8—C93.1 (2)C14—C15—C16—C17175.17 (16)
C5—N4—C9—C83.0 (2)C15—C16—C17—C181.1 (3)
C3—N4—C9—C8175.38 (15)C16—C17—C18—C190.4 (3)
C5—N4—C9—C1178.96 (14)C16—C17—C18—Br179.82 (13)
C3—N4—C9—C12.69 (18)C17—C18—C19—C200.8 (3)
C7—C8—C9—N40.1 (2)Br—C18—C19—C20178.68 (13)
C7—C8—C9—C1177.36 (18)C18—C19—C20—C151.2 (3)
C2—C1—C9—N42.60 (18)C16—C15—C20—C190.6 (3)
C10—C1—C9—N4172.51 (16)C14—C15—C20—C19176.50 (16)
C2—C1—C9—C8175.12 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H133···O12i0.982.453.419 (3)170
C17—H17···O10ii0.952.503.368 (2)152
C19—H19···O10iii0.952.313.249 (2)172
C23—H233···O14iv0.982.443.167 (2)131
C13—H131···Brv0.982.843.480 (2)123
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y1, z; (iii) x+1, y1, z; (iv) x+1, y+2, z; (v) x+1, y, z+1.
 

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