Di­methyl 3-benzoyl-7-(N,N-di­methylamino)­indolizine-1,2-di­carboxyl­ate

In the title compound, C₂₁H₂₀N₂O₅, the molecular packing is influenced by weak intermolecular C—H...O and C—H...π interactions. The carboxyl­ate groups are oriented perpendicular to each other and one of them is almost coplanar with the indolizine moiety.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.134
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.94
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N23    -   C25     ..       8.93 su

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           28.00
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               4265
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         4511
           Completeness (_total/calc)             94.55%
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.69 Ratio
PLAT480_ALERT_4_C Long H...A H-Bond Reported H123   ..  CG1     ..       2.93 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H243   ..  CG2     ..       2.79 Ang.

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   5 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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Dimethyl 3-benzoyl-7-(N,N-dimethylamino)indolizine-1,2-dicarboxylate

Crystal data

C21H20N2O5	F(000) = 800
Mr = 380.39	Dx = 1.354 Mg m^−3
Monoclinic, P121/c1	Melting point: 474 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.6333 (9) Å	Cell parameters from 4242 reflections
b = 27.515 (3) Å	θ = 2.4–27.5°
c = 7.9705 (9) Å	µ = 0.10 mm^−1
β = 99.781 (2)°	T = 293 K
V = 1865.8 (3) Å^3	Prism, yellow
Z = 4	0.30 × 0.25 × 0.18 mm

Data collection

Siemens SMART CCD area-detector diffractometer	3301 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 28.0°, θmin = 2.4°
ω scans	h = −11→11
11309 measured reflections	k = −35→33
4265 independent reflections	l = −8→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0689P)^2 + 0.3296P] where P = (Fo^2 + 2Fc^2)/3
4265 reflections	(Δ/σ)max < 0.001
257 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O10	0.55503 (13)	0.17172 (4)	0.55123 (16)	0.0585 (3)
O11	0.70431 (13)	0.10648 (5)	0.52864 (16)	0.0625 (3)
O13	0.17322 (13)	0.18573 (4)	0.45939 (14)	0.0539 (3)
O14	0.32871 (12)	0.20920 (4)	0.27516 (13)	0.0462 (3)
O16	−0.03088 (15)	0.05279 (5)	0.1263 (2)	0.0788 (4)
N4	0.30263 (14)	0.05008 (4)	0.22090 (16)	0.0424 (3)
N23	0.6416 (2)	−0.05699 (6)	0.2442 (3)	0.0759 (5)
C1	0.45149 (16)	0.10701 (5)	0.37280 (17)	0.0396 (3)
C2	0.30261 (15)	0.12656 (5)	0.31427 (17)	0.0375 (3)
C3	0.20763 (16)	0.09193 (5)	0.22123 (17)	0.0398 (3)
C5	0.2676 (2)	0.00662 (6)	0.1397 (2)	0.0528 (4)
H5	0.1672	0.0012	0.0790	0.063*
C6	0.3770 (2)	−0.02825 (6)	0.1471 (2)	0.0591 (4)
H6	0.3509	−0.0576	0.0915	0.071*
C7	0.5320 (2)	−0.02149 (6)	0.2377 (2)	0.0563 (4)
C8	0.56626 (19)	0.02301 (6)	0.3188 (2)	0.0499 (4)
H8	0.6665	0.0288	0.3793	0.060*
C9	0.45162 (16)	0.05887 (5)	0.30986 (18)	0.0418 (3)
C10	0.57210 (16)	0.13229 (6)	0.49069 (18)	0.0438 (3)
C12	0.8290 (2)	0.12930 (9)	0.6462 (3)	0.0889 (7)
H121	0.8860	0.1512	0.5852	0.133*
H122	0.8990	0.1048	0.7012	0.133*
H123	0.7848	0.1471	0.7303	0.133*
C13	0.25800 (15)	0.17662 (5)	0.35977 (17)	0.0393 (3)
C15	0.3138 (2)	0.25924 (6)	0.3218 (2)	0.0618 (5)
H151	0.2066	0.2694	0.2887	0.093*
H152	0.3807	0.2790	0.2652	0.093*
H153	0.3442	0.2627	0.4428	0.093*
C16	0.04137 (17)	0.09130 (6)	0.1540 (2)	0.0471 (4)
C17	−0.04683 (16)	0.13779 (6)	0.12006 (18)	0.0436 (3)
C18	0.01191 (18)	0.17752 (6)	0.0440 (2)	0.0497 (4)
H18	0.1122	0.1762	0.0163	0.060*
C19	−0.0775 (2)	0.21889 (7)	0.0091 (2)	0.0622 (5)
H19	−0.0376	0.2453	−0.0426	0.075*
C20	−0.2256 (2)	0.22129 (7)	0.0506 (3)	0.0698 (5)
H20	−0.2850	0.2495	0.0287	0.084*
C21	−0.2856 (2)	0.18198 (8)	0.1245 (3)	0.0704 (5)
H21	−0.3858	0.1836	0.1524	0.084*
C22	−0.19802 (19)	0.14028 (7)	0.1574 (2)	0.0565 (4)
H22	−0.2403	0.1136	0.2050	0.068*
C24	0.6079 (3)	−0.10327 (7)	0.1581 (3)	0.0930 (8)
H241	0.5199	−0.1183	0.1965	0.140*
H242	0.6981	−0.1241	0.1833	0.140*
H243	0.5834	−0.0980	0.0374	0.140*
C25	0.7989 (3)	−0.04904 (9)	0.3328 (4)	0.1008 (9)
H251	0.8493	−0.0249	0.2737	0.151*
H252	0.8571	−0.0789	0.3375	0.151*
H253	0.7954	−0.0380	0.4464	0.151*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O10	0.0526 (6)	0.0529 (7)	0.0653 (7)	−0.0016 (5)	−0.0038 (5)	−0.0138 (6)
O11	0.0455 (6)	0.0688 (8)	0.0676 (7)	0.0087 (5)	−0.0066 (5)	−0.0038 (6)
O13	0.0570 (6)	0.0533 (7)	0.0546 (7)	0.0034 (5)	0.0187 (5)	−0.0083 (5)
O14	0.0568 (6)	0.0336 (6)	0.0486 (6)	−0.0021 (4)	0.0102 (5)	−0.0011 (4)
O16	0.0543 (7)	0.0495 (8)	0.1273 (13)	−0.0125 (6)	0.0006 (7)	−0.0165 (8)
N4	0.0488 (6)	0.0327 (7)	0.0462 (7)	−0.0020 (5)	0.0093 (5)	−0.0001 (5)
N23	0.0889 (12)	0.0459 (9)	0.1005 (13)	0.0244 (8)	0.0375 (10)	0.0117 (9)
C1	0.0420 (7)	0.0366 (8)	0.0407 (7)	0.0002 (6)	0.0080 (6)	0.0012 (6)
C2	0.0394 (6)	0.0362 (8)	0.0373 (7)	−0.0021 (5)	0.0075 (5)	0.0011 (5)
C3	0.0435 (7)	0.0326 (7)	0.0433 (7)	−0.0012 (5)	0.0077 (6)	0.0002 (6)
C5	0.0659 (10)	0.0354 (8)	0.0586 (9)	−0.0070 (7)	0.0143 (8)	−0.0066 (7)
C6	0.0810 (12)	0.0349 (9)	0.0660 (11)	−0.0021 (8)	0.0254 (9)	−0.0038 (8)
C7	0.0760 (11)	0.0389 (9)	0.0614 (10)	0.0123 (8)	0.0326 (9)	0.0115 (7)
C8	0.0538 (8)	0.0435 (9)	0.0544 (9)	0.0084 (7)	0.0155 (7)	0.0101 (7)
C9	0.0468 (7)	0.0380 (8)	0.0420 (7)	0.0009 (6)	0.0118 (6)	0.0048 (6)
C10	0.0405 (7)	0.0473 (9)	0.0428 (7)	−0.0004 (6)	0.0048 (6)	0.0038 (6)
C12	0.0503 (10)	0.1049 (19)	0.0993 (17)	0.0060 (11)	−0.0226 (10)	−0.0131 (14)
C13	0.0389 (7)	0.0380 (8)	0.0394 (7)	−0.0002 (5)	0.0022 (5)	−0.0027 (6)
C15	0.0886 (13)	0.0334 (9)	0.0627 (10)	−0.0017 (8)	0.0106 (9)	−0.0028 (7)
C16	0.0447 (8)	0.0440 (9)	0.0515 (8)	−0.0078 (6)	0.0053 (6)	−0.0057 (7)
C17	0.0400 (7)	0.0464 (9)	0.0431 (8)	−0.0043 (6)	0.0029 (6)	−0.0029 (6)
C18	0.0406 (7)	0.0557 (10)	0.0512 (9)	−0.0059 (7)	0.0031 (6)	0.0045 (7)
C19	0.0561 (9)	0.0543 (11)	0.0723 (11)	−0.0062 (8)	−0.0003 (8)	0.0144 (9)
C20	0.0587 (10)	0.0544 (11)	0.0928 (14)	0.0108 (8)	0.0032 (9)	0.0039 (10)
C21	0.0510 (9)	0.0726 (13)	0.0908 (14)	0.0094 (9)	0.0215 (9)	0.0031 (11)
C22	0.0494 (9)	0.0587 (11)	0.0636 (10)	−0.0039 (7)	0.0163 (7)	0.0039 (8)
C24	0.143 (2)	0.0437 (11)	0.1106 (18)	0.0283 (12)	0.0730 (17)	0.0107 (11)
C25	0.0944 (17)	0.0780 (17)	0.138 (2)	0.0463 (14)	0.0409 (16)	0.0288 (15)

Geometric parameters (Å, º)

O10—C10	1.2065 (19)	C8—H8	0.9300
O11—C10	1.3347 (18)	C12—H121	0.9600
O11—C12	1.445 (2)	C12—H122	0.9600
O13—C13	1.1943 (17)	C12—H123	0.9600
O14—C13	1.3307 (17)	C15—H151	0.9600
O14—C15	1.4379 (19)	C15—H152	0.9600
O16—C16	1.2303 (19)	C15—H153	0.9600
N4—C5	1.369 (2)	C16—C17	1.490 (2)
N4—C9	1.3806 (19)	C17—C18	1.387 (2)
N4—C3	1.4140 (18)	C17—C22	1.389 (2)
N23—C7	1.355 (2)	C18—C19	1.377 (2)
N23—C25	1.437 (3)	C18—H18	0.9300
N23—C24	1.453 (3)	C19—C20	1.375 (3)
C1—C2	1.3983 (19)	C19—H19	0.9300
C1—C9	1.416 (2)	C20—C21	1.375 (3)
C1—C10	1.456 (2)	C20—H20	0.9300
C2—C3	1.3869 (19)	C21—C22	1.374 (3)
C2—C13	1.492 (2)	C21—H21	0.9300
C3—C16	1.445 (2)	C22—H22	0.9300
C5—C6	1.341 (2)	C24—H241	0.9600
C5—H5	0.9300	C24—H242	0.9600
C6—C7	1.420 (3)	C24—H243	0.9600
C6—H6	0.9300	C25—H251	0.9600
C7—C8	1.393 (2)	C25—H252	0.9600
C8—C9	1.391 (2)	C25—H253	0.9600
C10—O11—C12	115.46 (15)	O13—C13—C2	124.63 (13)
C13—O14—C15	116.42 (12)	O14—C13—C2	109.83 (11)
C5—N4—C9	120.50 (13)	O14—C15—H151	109.5
C5—N4—C3	129.10 (13)	O14—C15—H152	109.5
C9—N4—C3	110.27 (11)	H151—C15—H152	109.5
C7—N23—C25	120.32 (18)	O14—C15—H153	109.5
C7—N23—C24	122.1 (2)	H151—C15—H153	109.5
C25—N23—C24	117.56 (18)	H152—C15—H153	109.5
C2—C1—C9	107.31 (12)	O16—C16—C3	121.22 (15)
C2—C1—C10	123.21 (13)	O16—C16—C17	118.63 (14)
C9—C1—C10	129.20 (13)	C3—C16—C17	120.14 (13)
C3—C2—C1	109.91 (12)	C18—C17—C22	118.79 (15)
C3—C2—C13	127.65 (12)	C18—C17—C16	122.84 (14)
C1—C2—C13	122.33 (12)	C22—C17—C16	118.26 (14)
C2—C3—N4	105.66 (12)	C19—C18—C17	120.36 (15)
C2—C3—C16	131.81 (13)	C19—C18—H18	119.8
N4—C3—C16	121.99 (13)	C17—C18—H18	119.8
C6—C5—N4	120.47 (16)	C20—C19—C18	120.22 (17)
C6—C5—H5	119.8	C20—C19—H19	119.9
N4—C5—H5	119.8	C18—C19—H19	119.9
C5—C6—C7	121.62 (16)	C21—C20—C19	119.92 (17)
C5—C6—H6	119.2	C21—C20—H20	120.0
C7—C6—H6	119.2	C19—C20—H20	120.0
N23—C7—C8	121.59 (18)	C22—C21—C20	120.22 (17)
N23—C7—C6	121.10 (17)	C22—C21—H21	119.9
C8—C7—C6	117.31 (15)	C20—C21—H21	119.9
C9—C8—C7	120.44 (16)	C21—C22—C17	120.46 (17)
C9—C8—H8	119.8	C21—C22—H22	119.8
C7—C8—H8	119.8	C17—C22—H22	119.8
N4—C9—C8	119.65 (14)	N23—C24—H241	109.5
N4—C9—C1	106.80 (12)	N23—C24—H242	109.5
C8—C9—C1	133.53 (14)	H241—C24—H242	109.5
O10—C10—O11	123.08 (14)	N23—C24—H243	109.5
O10—C10—C1	124.43 (13)	H241—C24—H243	109.5
O11—C10—C1	112.48 (14)	H242—C24—H243	109.5
O11—C12—H121	109.5	N23—C25—H251	109.5
O11—C12—H122	109.5	N23—C25—H252	109.5
H121—C12—H122	109.5	H251—C25—H252	109.5
O11—C12—H123	109.5	N23—C25—H253	109.5
H121—C12—H123	109.5	H251—C25—H253	109.5
H122—C12—H123	109.5	H252—C25—H253	109.5
O13—C13—O14	125.54 (14)
C9—C1—C2—C3	1.85 (16)	C2—C1—C9—C8	176.43 (15)
C10—C1—C2—C3	−172.60 (13)	C10—C1—C9—C8	−9.6 (3)
C9—C1—C2—C13	178.34 (12)	C12—O11—C10—O10	−1.1 (2)
C10—C1—C2—C13	3.9 (2)	C12—O11—C10—C1	−179.61 (16)
C1—C2—C3—N4	−0.89 (15)	C2—C1—C10—O10	1.4 (2)
C13—C2—C3—N4	−177.14 (12)	C9—C1—C10—O10	−171.81 (15)
C1—C2—C3—C16	170.55 (15)	C2—C1—C10—O11	179.85 (13)
C13—C2—C3—C16	−5.7 (3)	C9—C1—C10—O11	6.7 (2)
C5—N4—C3—C2	−176.36 (14)	C15—O14—C13—O13	6.8 (2)
C9—N4—C3—C2	−0.44 (15)	C15—O14—C13—C2	−172.16 (12)
C5—N4—C3—C16	11.2 (2)	C3—C2—C13—O13	70.2 (2)
C9—N4—C3—C16	−172.92 (13)	C1—C2—C13—O13	−105.64 (17)
C9—N4—C5—C6	0.8 (2)	C3—C2—C13—O14	−110.84 (15)
C3—N4—C5—C6	176.32 (15)	C1—C2—C13—O14	73.33 (16)
N4—C5—C6—C7	−0.3 (3)	C2—C3—C16—O16	−154.96 (17)
C25—N23—C7—C8	−1.5 (3)	N4—C3—C16—O16	15.3 (2)
C24—N23—C7—C8	−179.05 (17)	C2—C3—C16—C17	23.7 (2)
C25—N23—C7—C6	178.36 (18)	N4—C3—C16—C17	−166.01 (13)
C24—N23—C7—C6	0.8 (3)	O16—C16—C17—C18	−138.52 (17)
C5—C6—C7—N23	−179.99 (16)	C3—C16—C17—C18	42.8 (2)
C5—C6—C7—C8	−0.2 (2)	O16—C16—C17—C22	37.6 (2)
N23—C7—C8—C9	179.89 (15)	C3—C16—C17—C22	−141.10 (15)
C6—C7—C8—C9	0.1 (2)	C22—C17—C18—C19	1.1 (2)
C5—N4—C9—C8	−0.9 (2)	C16—C17—C18—C19	177.25 (15)
C3—N4—C9—C8	−177.18 (13)	C17—C18—C19—C20	0.4 (3)
C5—N4—C9—C1	177.89 (13)	C18—C19—C20—C21	−1.1 (3)
C3—N4—C9—C1	1.56 (15)	C19—C20—C21—C22	0.1 (3)
C7—C8—C9—N4	0.4 (2)	C20—C21—C22—C17	1.5 (3)
C7—C8—C9—C1	−177.90 (15)	C18—C17—C22—C21	−2.1 (3)
C2—C1—C9—N4	−2.06 (15)	C16—C17—C22—C21	−178.39 (17)
C10—C1—C9—N4	171.95 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O16^i	0.93	2.37	3.142 (2)	140
C20—H20···O10^ii	0.93	2.59	3.501 (2)	165
C12—H123···Cg1^iii	0.96	2.93	3.721 (3)	141
C24—H243···Cg2^iv	0.96	2.79	3.677 (2)	154

Symmetry codes: (i) −x, −y, −z; (ii) x−1, −y+1/2, z−1/2; (iii) x+1, y, z+1; (iv) −x+1, −y, −z.