Di­methyl 7-(N,N-di­methyl­amino)-3-(4-methyl­benzoyl)­indolizine-1,2-di­carboxyl­ate

Hema, R.; Parthasarathi, V.; Ravikumar, K.; Sarkunam, K.; Nallu, M.

doi:10.1107/S1600536804004805

Dimethyl 7-(N,N-dimethylamino)-3-(4-methylbenzoyl)indolizine-1,2-dicarboxylate

R. Hema, V. Parthasarathi, K. Ravikumar, K. Sarkunam and M. Nallu

In the title compound, C₂₂H₂₂N₂O₅, there are two molecules in the asymmetric unit. In each of them, the carboxylate groups are oriented perpendicular to each other and one of the carboxylate groups is almost coplanar with the indolizine moiety. In the solid state, weak intermolecular C—H

O contacts are observed.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804004805/cv6277sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804004805/cv6277Isup2.hkl Contains datablock I

CCDC reference: 238776

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.057
wR factor = 0.156
Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level A
REFLT03_ALERT_3_A  Reflection count < 85% complete (theta max?)
           From the CIF: _diffrn_reflns_theta_max           28.07
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               8081
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         9742
           Completeness (_total/calc)             82.95%
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.83

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.70 Ratio

   2 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

Dimethyl 7-(N,N-dimethylamino)3-(4-methylbenzoyl)indolizine-1,2-dicarboxylate top

Crystal data top

C₂₂H₂₂N₂O₅	F(000) = 832
M_r = 394.42	D_x = 1.308 Mg m⁻³
Triclinic, P1	Melting point: 443 K
a = 8.050 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 16.942 (11) Å	Cell parameters from 3068 reflections
c = 17.094 (11) Å	θ = 2.4–24.5°
α = 118.555 (10)°	µ = 0.09 mm⁻¹
β = 95.033 (12)°	T = 293 K
γ = 97.082 (11)°	Prism, yellow
V = 2003 (2) Å³	0.28 × 0.20 × 0.15 mm
Z = 4

Data collection top

Siemens SMART CCD area-detector diffractometer	5203 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.018
Graphite monochromator	θ_max = 28.1°, θ_min = 2.4°
ω scans	h = −10→9
12347 measured reflections	k = −22→17
8081 independent reflections	l = −22→22

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0707P)² + 0.2476P] where P = (F_o² + 2F_c²)/3
8081 reflections	(Δ/σ)_max < 0.001
533 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

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

	x	y	z	U_iso*/U_eq
O10A	−0.1046 (2)	0.66197 (11)	0.06884 (10)	0.0717 (5)
O11A	−0.07127 (18)	0.78098 (10)	0.04524 (9)	0.0640 (4)
O13A	−0.0319 (2)	0.66466 (11)	0.26598 (11)	0.0760 (5)
O14A	0.15212 (19)	0.61766 (10)	0.16881 (10)	0.0654 (4)
O16A	0.3212 (2)	0.93480 (12)	0.47023 (10)	0.0862 (5)
N4A	0.2496 (2)	0.91835 (11)	0.29569 (10)	0.0507 (4)
N23A	0.2511 (3)	1.10157 (14)	0.20101 (16)	0.0818 (6)
C1A	0.0839 (2)	0.79758 (14)	0.17515 (13)	0.0480 (5)
C2A	0.1346 (2)	0.77133 (13)	0.23855 (12)	0.0467 (5)
C3A	0.2365 (2)	0.84506 (13)	0.31358 (13)	0.0491 (5)
C5A	0.3436 (3)	1.00483 (15)	0.34640 (15)	0.0612 (6)
H51	0.4067	1.0226	0.4023	0.073*
C6A	0.3446 (3)	1.06401 (15)	0.31513 (16)	0.0667 (6)
H61	0.4089	1.1227	0.3503	0.080*
C7A	0.2503 (3)	1.03974 (16)	0.23000 (16)	0.0607 (6)
C8A	0.1599 (2)	0.95140 (15)	0.17880 (15)	0.0560 (5)
H81	0.0987	0.9327	0.1221	0.067*
C9A	0.1594 (2)	0.89032 (14)	0.21119 (13)	0.0489 (5)
C10A	−0.0381 (2)	0.73922 (16)	0.09249 (13)	0.0511 (5)
C12A	−0.1887 (3)	0.72787 (18)	−0.03863 (15)	0.0829 (8)
H121	−0.1316	0.6875	−0.0844	0.124*
H122	−0.2313	0.7682	−0.0568	0.124*
H123	−0.2816	0.6926	−0.0306	0.124*
C13A	0.0738 (3)	0.67960 (15)	0.22754 (14)	0.0536 (5)
C15A	0.0966 (4)	0.52447 (17)	0.1479 (2)	0.1001 (10)
H151	0.1321	0.5184	0.1996	0.150*
H152	0.1458	0.4842	0.0979	0.150*
H153	−0.0249	0.5087	0.1324	0.150*
C16A	0.2987 (3)	0.85904 (16)	0.40265 (14)	0.0570 (5)
C17A	0.3340 (2)	0.78000 (15)	0.41182 (13)	0.0531 (5)
C18A	0.4023 (3)	0.71133 (16)	0.34850 (15)	0.0639 (6)
H181	0.4243	0.7124	0.2965	0.077*
C19A	0.4381 (3)	0.64105 (18)	0.36199 (18)	0.0805 (7)
H191	0.4862	0.5955	0.3191	0.097*
C20A	0.4045 (3)	0.6365 (2)	0.4374 (2)	0.0800 (8)
C21A	0.3372 (3)	0.7053 (2)	0.50026 (19)	0.0796 (8)
H211	0.3135	0.7036	0.5517	0.095*
C22A	0.3042 (3)	0.77669 (18)	0.48886 (15)	0.0682 (6)
H221	0.2611	0.8236	0.5333	0.082*
C24A	0.3476 (3)	1.19378 (18)	0.2544 (2)	0.0986 (10)
H241	0.3185	1.2214	0.3139	0.148*
H242	0.3218	1.2290	0.2262	0.148*
H243	0.4668	1.1922	0.2586	0.148*
C25A	0.1581 (4)	1.0762 (2)	0.1132 (2)	0.1014 (10)
H251	0.2053	1.0299	0.0667	0.152*
H252	0.1666	1.1290	0.1054	0.152*
H253	0.0409	1.0529	0.1093	0.152*
C26A	0.4475 (4)	0.5597 (2)	0.4520 (3)	0.1257 (13)
H261	0.3954	0.5020	0.4002	0.188*
H262	0.4058	0.5641	0.5046	0.188*
H263	0.5684	0.5641	0.4604	0.188*
O10B	1.1229 (2)	0.32098 (13)	0.43379 (11)	0.0897 (6)
O11B	1.05222 (19)	0.19024 (13)	0.43590 (10)	0.0794 (5)
O13B	1.0654 (2)	0.35263 (12)	0.25191 (11)	0.0860 (5)
O14B	0.8881 (2)	0.39787 (11)	0.35265 (11)	0.0757 (5)
O16B	0.6602 (2)	0.11096 (11)	0.03236 (10)	0.0863 (5)
N4B	0.7416 (2)	0.09628 (12)	0.18983 (10)	0.0523 (4)
N23B	0.6976 (2)	−0.11839 (14)	0.24370 (13)	0.0702 (5)
C1B	0.9187 (2)	0.20042 (15)	0.31644 (13)	0.0567 (5)
C2B	0.8787 (2)	0.24149 (15)	0.26479 (13)	0.0540 (5)
C3B	0.7687 (2)	0.17773 (14)	0.18561 (13)	0.0528 (5)
C5B	0.6378 (3)	0.01427 (15)	0.13067 (14)	0.0587 (6)
H52	0.5771	0.0067	0.0779	0.070*
C6B	0.6233 (3)	−0.05490 (16)	0.14809 (14)	0.0607 (6)
H62	0.5521	−0.1100	0.1069	0.073*
C7B	0.7134 (3)	−0.04680 (16)	0.22782 (14)	0.0582 (5)
C8B	0.8151 (2)	0.03729 (16)	0.28764 (14)	0.0583 (6)
H82	0.8747	0.0459	0.3411	0.070*
C9B	0.8293 (2)	0.10854 (15)	0.26921 (13)	0.0524 (5)
C10B	1.0404 (3)	0.24509 (19)	0.40039 (14)	0.0655 (6)
C12B	1.1649 (4)	0.2275 (2)	0.52090 (17)	0.1092 (11)
H124	1.2761	0.2503	0.5155	0.164*
H125	1.1711	0.1805	0.5366	0.164*
H126	1.1226	0.2766	0.5671	0.164*
C13B	0.9565 (3)	0.33596 (17)	0.28766 (14)	0.0630 (6)
C15B	0.9540 (4)	0.49230 (18)	0.3808 (2)	0.1104 (11)
H154	1.0751	0.5048	0.3983	0.166*
H155	0.9042	0.5313	0.4313	0.166*
H156	0.9266	0.5036	0.3317	0.166*
C16B	0.7029 (3)	0.18132 (16)	0.10638 (14)	0.0596 (6)
C17B	0.6836 (2)	0.26978 (15)	0.11219 (13)	0.0548 (5)
C18B	0.6252 (3)	0.33671 (16)	0.18342 (15)	0.0647 (6)
H182	0.6044	0.3290	0.2322	0.078*
C19B	0.5978 (3)	0.41448 (18)	0.18257 (17)	0.0762 (7)
H192	0.5560	0.4581	0.2307	0.091*
C20B	0.6298 (3)	0.43039 (18)	0.11318 (18)	0.0728 (7)
C21B	0.6867 (3)	0.3625 (2)	0.04142 (17)	0.0748 (7)
H212	0.7084	0.3708	−0.0070	0.090*
C22B	0.7117 (3)	0.28339 (18)	0.04011 (15)	0.0654 (6)
H222	0.7478	0.2384	−0.0095	0.078*
C24B	0.5915 (3)	−0.20534 (17)	0.18085 (17)	0.0769 (7)
H244	0.4745	−0.2009	0.1850	0.115*
H245	0.6193	−0.2511	0.1950	0.115*
H246	0.6098	−0.2220	0.1206	0.115*
C25B	0.7786 (4)	−0.10709 (19)	0.32845 (17)	0.0845 (8)
H254	0.8976	−0.0831	0.3383	0.127*
H255	0.7637	−0.1653	0.3262	0.127*
H256	0.7281	−0.0654	0.3770	0.127*
C26B	0.6012 (4)	0.5175 (2)	0.1149 (2)	0.1064 (10)
H264	0.6684	0.5283	0.0761	0.160*
H265	0.6337	0.5678	0.1755	0.160*
H266	0.4832	0.5119	0.0943	0.160*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O10A	0.0813 (11)	0.0604 (10)	0.0619 (9)	−0.0087 (9)	−0.0103 (8)	0.0299 (9)
O11A	0.0683 (9)	0.0666 (10)	0.0555 (8)	0.0031 (8)	−0.0043 (7)	0.0337 (8)
O13A	0.0802 (11)	0.0720 (12)	0.0743 (10)	−0.0020 (9)	0.0200 (9)	0.0377 (10)
O14A	0.0725 (10)	0.0434 (9)	0.0681 (10)	0.0119 (8)	0.0106 (8)	0.0180 (8)
O16A	0.1305 (15)	0.0585 (11)	0.0482 (9)	0.0117 (10)	−0.0009 (9)	0.0135 (9)
N4A	0.0529 (9)	0.0420 (10)	0.0491 (9)	0.0094 (8)	0.0065 (7)	0.0166 (8)
N23A	0.0973 (15)	0.0591 (14)	0.1051 (17)	0.0216 (12)	0.0281 (13)	0.0497 (14)
C1A	0.0489 (11)	0.0457 (13)	0.0469 (11)	0.0100 (9)	0.0088 (8)	0.0206 (10)
C2A	0.0485 (10)	0.0440 (12)	0.0441 (10)	0.0113 (9)	0.0098 (8)	0.0182 (10)
C3A	0.0527 (11)	0.0423 (12)	0.0493 (11)	0.0127 (9)	0.0081 (9)	0.0194 (10)
C5A	0.0623 (13)	0.0464 (14)	0.0576 (13)	0.0043 (11)	0.0041 (10)	0.0146 (12)
C6A	0.0677 (14)	0.0434 (14)	0.0768 (16)	0.0075 (11)	0.0168 (12)	0.0202 (13)
C7A	0.0607 (13)	0.0526 (15)	0.0778 (15)	0.0206 (11)	0.0265 (11)	0.0345 (13)
C8A	0.0543 (12)	0.0569 (15)	0.0634 (13)	0.0148 (10)	0.0138 (10)	0.0332 (12)
C9A	0.0452 (10)	0.0479 (13)	0.0513 (11)	0.0137 (9)	0.0109 (8)	0.0213 (10)
C10A	0.0497 (11)	0.0556 (15)	0.0480 (11)	0.0096 (10)	0.0093 (9)	0.0254 (11)
C12A	0.0914 (18)	0.091 (2)	0.0583 (14)	0.0022 (15)	−0.0146 (12)	0.0385 (14)
C13A	0.0569 (12)	0.0517 (14)	0.0480 (11)	0.0050 (10)	0.0018 (9)	0.0238 (11)
C15A	0.105 (2)	0.0410 (16)	0.131 (3)	0.0065 (14)	0.0111 (19)	0.0274 (17)
C16A	0.0584 (12)	0.0543 (14)	0.0471 (12)	0.0070 (10)	0.0036 (9)	0.0180 (12)
C17A	0.0485 (11)	0.0572 (14)	0.0480 (11)	0.0066 (10)	0.0008 (9)	0.0237 (11)
C18A	0.0683 (14)	0.0679 (16)	0.0583 (13)	0.0176 (12)	0.0066 (11)	0.0331 (13)
C19A	0.0910 (18)	0.0710 (18)	0.0796 (17)	0.0293 (14)	0.0072 (14)	0.0351 (16)
C20A	0.0686 (16)	0.084 (2)	0.103 (2)	0.0092 (14)	−0.0038 (14)	0.0626 (18)
C21A	0.0711 (16)	0.107 (2)	0.0853 (18)	0.0103 (15)	0.0108 (14)	0.0682 (19)
C22A	0.0634 (13)	0.0866 (19)	0.0607 (14)	0.0156 (12)	0.0119 (11)	0.0407 (14)
C24A	0.0915 (19)	0.0644 (19)	0.159 (3)	0.0193 (15)	0.051 (2)	0.064 (2)
C25A	0.133 (3)	0.095 (2)	0.116 (2)	0.0403 (19)	0.034 (2)	0.077 (2)
C26A	0.121 (3)	0.127 (3)	0.178 (4)	0.029 (2)	0.006 (2)	0.115 (3)
O10B	0.0795 (11)	0.0869 (14)	0.0636 (10)	−0.0141 (10)	−0.0152 (9)	0.0178 (10)
O11B	0.0660 (10)	0.1033 (14)	0.0566 (9)	0.0032 (9)	−0.0099 (7)	0.0361 (10)
O13B	0.0790 (11)	0.0867 (13)	0.0763 (11)	−0.0057 (9)	0.0228 (9)	0.0311 (10)
O14B	0.0808 (11)	0.0562 (11)	0.0596 (9)	0.0006 (8)	0.0110 (8)	0.0075 (9)
O16B	0.1274 (15)	0.0626 (11)	0.0455 (9)	0.0055 (10)	−0.0085 (9)	0.0151 (9)
N4B	0.0511 (9)	0.0519 (11)	0.0408 (9)	0.0103 (8)	0.0034 (7)	0.0133 (8)
N23B	0.0824 (13)	0.0640 (14)	0.0644 (12)	0.0183 (11)	0.0094 (10)	0.0313 (11)
C1B	0.0487 (11)	0.0648 (15)	0.0431 (11)	0.0083 (10)	0.0054 (9)	0.0170 (11)
C2B	0.0476 (11)	0.0554 (14)	0.0425 (10)	0.0061 (10)	0.0080 (8)	0.0121 (10)
C3B	0.0529 (11)	0.0510 (14)	0.0431 (11)	0.0098 (10)	0.0067 (9)	0.0145 (10)
C5B	0.0595 (12)	0.0554 (15)	0.0457 (11)	0.0076 (11)	−0.0017 (9)	0.0153 (11)
C6B	0.0598 (13)	0.0538 (14)	0.0523 (12)	0.0090 (11)	0.0053 (10)	0.0145 (11)
C7B	0.0547 (12)	0.0622 (16)	0.0539 (12)	0.0190 (11)	0.0145 (10)	0.0232 (12)
C8B	0.0534 (12)	0.0709 (16)	0.0470 (11)	0.0184 (11)	0.0074 (9)	0.0251 (12)
C9B	0.0448 (10)	0.0614 (14)	0.0413 (10)	0.0120 (10)	0.0051 (8)	0.0176 (11)
C10B	0.0498 (12)	0.0826 (19)	0.0450 (12)	0.0060 (12)	0.0040 (9)	0.0188 (13)
C12B	0.0926 (19)	0.154 (3)	0.0643 (16)	0.003 (2)	−0.0223 (14)	0.0512 (19)
C13B	0.0587 (13)	0.0641 (16)	0.0446 (12)	−0.0011 (11)	0.0023 (10)	0.0140 (12)
C15B	0.127 (3)	0.0553 (18)	0.102 (2)	−0.0067 (17)	0.0098 (19)	0.0096 (17)
C16B	0.0585 (12)	0.0607 (15)	0.0432 (11)	0.0041 (11)	0.0016 (9)	0.0157 (11)
C17B	0.0486 (11)	0.0578 (15)	0.0483 (11)	0.0000 (10)	0.0030 (9)	0.0217 (11)
C18B	0.0734 (15)	0.0629 (16)	0.0571 (13)	0.0088 (12)	0.0146 (11)	0.0294 (13)
C19B	0.0881 (17)	0.0647 (18)	0.0743 (16)	0.0174 (14)	0.0175 (13)	0.0318 (15)
C20B	0.0680 (15)	0.0699 (17)	0.0790 (17)	−0.0027 (13)	−0.0022 (13)	0.0417 (15)
C21B	0.0675 (15)	0.092 (2)	0.0689 (16)	−0.0077 (14)	0.0009 (12)	0.0498 (16)
C22B	0.0581 (13)	0.0767 (18)	0.0543 (13)	0.0023 (12)	0.0075 (10)	0.0295 (13)
C24B	0.0858 (17)	0.0648 (17)	0.0784 (17)	0.0146 (14)	0.0231 (14)	0.0324 (15)
C25B	0.1005 (19)	0.085 (2)	0.0783 (17)	0.0269 (16)	0.0152 (15)	0.0459 (16)
C26B	0.114 (2)	0.098 (2)	0.128 (3)	0.0083 (19)	0.0018 (19)	0.077 (2)

Geometric parameters (Å, º) top

O10A—C10A	1.203 (2)	O10B—C10B	1.201 (3)
O11A—C10A	1.334 (2)	O11B—C10B	1.339 (3)
O11A—C12A	1.442 (3)	O11B—C12B	1.443 (3)
O13A—C13A	1.193 (2)	O13B—C13B	1.191 (3)
O14A—C13A	1.332 (3)	O14B—C13B	1.332 (3)
O14A—C15A	1.442 (3)	O14B—C15B	1.443 (3)
O16A—C16A	1.226 (3)	O16B—C16B	1.233 (2)
N4A—C5A	1.367 (3)	N4B—C5B	1.369 (3)
N4A—C9A	1.383 (3)	N4B—C9B	1.382 (2)
N4A—C3A	1.408 (3)	N4B—C3B	1.407 (3)
N23A—C7A	1.356 (3)	N23B—C7B	1.358 (3)
N23A—C24A	1.446 (3)	N23B—C24B	1.439 (3)
N23A—C25A	1.451 (4)	N23B—C25B	1.449 (3)
C1A—C2A	1.403 (3)	C1B—C2B	1.400 (3)
C1A—C9A	1.411 (3)	C1B—C9B	1.419 (3)
C1A—C10A	1.456 (3)	C1B—C10B	1.457 (3)
C2A—C3A	1.382 (3)	C2B—C3B	1.393 (3)
C2A—C13A	1.486 (3)	C2B—C13B	1.490 (3)
C3A—C16A	1.455 (3)	C3B—C16B	1.442 (3)
C5A—C6A	1.343 (3)	C5B—C6B	1.335 (3)
C5A—H51	0.9300	C5B—H52	0.9300
C6A—C7A	1.421 (3)	C6B—C7B	1.423 (3)
C6A—H61	0.9300	C6B—H62	0.9300
C7A—C8A	1.380 (3)	C7B—C8B	1.385 (3)
C8A—C9A	1.387 (3)	C8B—C9B	1.380 (3)
C8A—H81	0.9300	C8B—H82	0.9300
C12A—H121	0.9600	C12B—H124	0.9600
C12A—H122	0.9600	C12B—H125	0.9600
C12A—H123	0.9600	C12B—H126	0.9600
C15A—H151	0.9600	C15B—H154	0.9600
C15A—H152	0.9600	C15B—H155	0.9600
C15A—H153	0.9600	C15B—H156	0.9600
C16A—C17A	1.478 (3)	C16B—C17B	1.483 (3)
C17A—C18A	1.373 (3)	C17B—C18B	1.379 (3)
C17A—C22A	1.385 (3)	C17B—C22B	1.389 (3)
C18A—C19A	1.375 (3)	C18B—C19B	1.369 (3)
C18A—H181	0.9300	C18B—H182	0.9300
C19A—C20A	1.376 (4)	C19B—C20B	1.374 (3)
C19A—H191	0.9300	C19B—H192	0.9300
C20A—C21A	1.366 (4)	C20B—C21B	1.384 (4)
C20A—C26A	1.510 (4)	C20B—C26B	1.509 (4)
C21A—C22A	1.366 (3)	C21B—C22B	1.370 (3)
C21A—H211	0.9300	C21B—H212	0.9300
C22A—H221	0.9300	C22B—H222	0.9300
C24A—H241	0.9600	C24B—H244	0.9600
C24A—H242	0.9600	C24B—H245	0.9600
C24A—H243	0.9600	C24B—H246	0.9600
C25A—H251	0.9600	C25B—H254	0.9600
C25A—H252	0.9600	C25B—H255	0.9600
C25A—H253	0.9600	C25B—H256	0.9600
C26A—H261	0.9600	C26B—H264	0.9600
C26A—H262	0.9600	C26B—H265	0.9600
C26A—H263	0.9600	C26B—H266	0.9600

C10A—O11A—C12A	116.68 (18)	C10B—O11B—C12B	117.1 (2)
C13A—O14A—C15A	116.01 (19)	C13B—O14B—C15B	116.0 (2)
C5A—N4A—C9A	120.60 (18)	C5B—N4B—C9B	119.96 (19)
C5A—N4A—C3A	128.98 (18)	C5B—N4B—C3B	129.07 (18)
C9A—N4A—C3A	110.26 (16)	C9B—N4B—C3B	110.86 (17)
C7A—N23A—C24A	121.8 (2)	C7B—N23B—C24B	121.8 (2)
C7A—N23A—C25A	120.7 (2)	C7B—N23B—C25B	120.4 (2)
C24A—N23A—C25A	117.5 (2)	C24B—N23B—C25B	117.7 (2)
C2A—C1A—C9A	107.37 (17)	C2B—C1B—C9B	107.76 (18)
C2A—C1A—C10A	123.98 (19)	C2B—C1B—C10B	124.4 (2)
C9A—C1A—C10A	128.39 (18)	C9B—C1B—C10B	127.8 (2)
C3A—C2A—C1A	109.71 (18)	C3B—C2B—C1B	109.5 (2)
C3A—C2A—C13A	126.39 (17)	C3B—C2B—C13B	125.77 (19)
C1A—C2A—C13A	123.72 (17)	C1B—C2B—C13B	124.51 (18)
C2A—C3A—N4A	105.95 (17)	C2B—C3B—N4B	105.70 (18)
C2A—C3A—C16A	131.72 (19)	C2B—C3B—C16B	132.0 (2)
N4A—C3A—C16A	121.43 (18)	N4B—C3B—C16B	121.91 (18)
C6A—C5A—N4A	119.7 (2)	C6B—C5B—N4B	120.5 (2)
C6A—C5A—H51	120.1	C6B—C5B—H52	119.8
N4A—C5A—H51	120.1	N4B—C5B—H52	119.8
C5A—C6A—C7A	122.0 (2)	C5B—C6B—C7B	122.0 (2)
C5A—C6A—H61	119.0	C5B—C6B—H62	119.0
C7A—C6A—H61	119.0	C7B—C6B—H62	119.0
N23A—C7A—C8A	122.0 (2)	N23B—C7B—C8B	122.5 (2)
N23A—C7A—C6A	120.7 (2)	N23B—C7B—C6B	120.9 (2)
C8A—C7A—C6A	117.3 (2)	C8B—C7B—C6B	116.6 (2)
C7A—C8A—C9A	120.5 (2)	C9B—C8B—C7B	121.1 (2)
C7A—C8A—H81	119.8	C9B—C8B—H82	119.5
C9A—C8A—H81	119.8	C7B—C8B—H82	119.5
N4A—C9A—C8A	119.76 (19)	C8B—C9B—N4B	119.87 (19)
N4A—C9A—C1A	106.68 (16)	C8B—C9B—C1B	133.93 (19)
C8A—C9A—C1A	133.56 (19)	N4B—C9B—C1B	106.20 (18)
O10A—C10A—O11A	122.81 (18)	O10B—C10B—O11B	123.3 (2)
O10A—C10A—C1A	124.46 (18)	O10B—C10B—C1B	125.0 (2)
O11A—C10A—C1A	112.73 (19)	O11B—C10B—C1B	111.6 (2)
O11A—C12A—H121	109.5	O11B—C12B—H124	109.5
O11A—C12A—H122	109.5	O11B—C12B—H125	109.5
H121—C12A—H122	109.5	H124—C12B—H125	109.5
O11A—C12A—H123	109.5	O11B—C12B—H126	109.5
H121—C12A—H123	109.5	H124—C12B—H126	109.5
H122—C12A—H123	109.5	H125—C12B—H126	109.5
O13A—C13A—O14A	125.6 (2)	O13B—C13B—O14B	125.4 (2)
O13A—C13A—C2A	123.9 (2)	O13B—C13B—C2B	123.8 (2)
O14A—C13A—C2A	110.58 (18)	O14B—C13B—C2B	110.88 (19)
O14A—C15A—H151	109.5	O14B—C15B—H154	109.5
O14A—C15A—H152	109.5	O14B—C15B—H155	109.5
H151—C15A—H152	109.5	H154—C15B—H155	109.5
O14A—C15A—H153	109.5	O14B—C15B—H156	109.5
H151—C15A—H153	109.5	H154—C15B—H156	109.5
H152—C15A—H153	109.5	H155—C15B—H156	109.5
O16A—C16A—C3A	121.4 (2)	O16B—C16B—C3B	120.9 (2)
O16A—C16A—C17A	119.38 (19)	O16B—C16B—C17B	118.39 (19)
C3A—C16A—C17A	119.22 (19)	C3B—C16B—C17B	120.70 (19)
C18A—C17A—C22A	118.5 (2)	C18B—C17B—C22B	118.2 (2)
C18A—C17A—C16A	122.48 (19)	C18B—C17B—C16B	122.45 (19)
C22A—C17A—C16A	119.0 (2)	C22B—C17B—C16B	119.2 (2)
C17A—C18A—C19A	120.0 (2)	C19B—C18B—C17B	120.3 (2)
C17A—C18A—H181	120.0	C19B—C18B—H182	119.9
C19A—C18A—H181	120.0	C17B—C18B—H182	119.9
C18A—C19A—C20A	121.5 (3)	C18B—C19B—C20B	122.4 (3)
C18A—C19A—H191	119.2	C18B—C19B—H192	118.8
C20A—C19A—H191	119.2	C20B—C19B—H192	118.8
C21A—C20A—C19A	118.0 (2)	C19B—C20B—C21B	117.1 (2)
C21A—C20A—C26A	121.1 (3)	C19B—C20B—C26B	121.1 (3)
C19A—C20A—C26A	120.8 (3)	C21B—C20B—C26B	121.8 (2)
C22A—C21A—C20A	121.2 (2)	C22B—C21B—C20B	121.4 (2)
C22A—C21A—H211	119.4	C22B—C21B—H212	119.3
C20A—C21A—H211	119.4	C20B—C21B—H212	119.3
C21A—C22A—C17A	120.7 (2)	C21B—C22B—C17B	120.6 (2)
C21A—C22A—H221	119.6	C21B—C22B—H222	119.7
C17A—C22A—H221	119.6	C17B—C22B—H222	119.7
N23A—C24A—H241	109.5	N23B—C24B—H244	109.5
N23A—C24A—H242	109.5	N23B—C24B—H245	109.5
H241—C24A—H242	109.5	H244—C24B—H245	109.5
N23A—C24A—H243	109.5	N23B—C24B—H246	109.5
H241—C24A—H243	109.5	H244—C24B—H246	109.5
H242—C24A—H243	109.5	H245—C24B—H246	109.5
N23A—C25A—H251	109.5	N23B—C25B—H254	109.5
N23A—C25A—H252	109.5	N23B—C25B—H255	109.5
H251—C25A—H252	109.5	H254—C25B—H255	109.5
N23A—C25A—H253	109.5	N23B—C25B—H256	109.5
H251—C25A—H253	109.5	H254—C25B—H256	109.5
H252—C25A—H253	109.5	H255—C25B—H256	109.5
C20A—C26A—H261	109.5	C20B—C26B—H264	109.5
C20A—C26A—H262	109.5	C20B—C26B—H265	109.5
H261—C26A—H262	109.5	H264—C26B—H265	109.5
C20A—C26A—H263	109.5	C20B—C26B—H266	109.5
H261—C26A—H263	109.5	H264—C26B—H266	109.5
H262—C26A—H263	109.5	H265—C26B—H266	109.5

C9A—C1A—C2A—C3A	1.2 (2)	C9B—C1B—C2B—C3B	−0.9 (2)
C10A—C1A—C2A—C3A	−173.46 (18)	C10B—C1B—C2B—C3B	175.27 (19)
C9A—C1A—C2A—C13A	176.56 (18)	C9B—C1B—C2B—C13B	−175.29 (19)
C10A—C1A—C2A—C13A	1.9 (3)	C10B—C1B—C2B—C13B	0.9 (3)
C1A—C2A—C3A—N4A	−0.3 (2)	C1B—C2B—C3B—N4B	0.1 (2)
C13A—C2A—C3A—N4A	−175.58 (18)	C13B—C2B—C3B—N4B	174.39 (19)
C1A—C2A—C3A—C16A	168.6 (2)	C1B—C2B—C3B—C16B	−172.9 (2)
C13A—C2A—C3A—C16A	−6.7 (4)	C13B—C2B—C3B—C16B	1.3 (4)
C5A—N4A—C3A—C2A	−176.01 (19)	C5B—N4B—C3B—C2B	176.84 (19)
C9A—N4A—C3A—C2A	−0.6 (2)	C9B—N4B—C3B—C2B	0.8 (2)
C5A—N4A—C3A—C16A	13.7 (3)	C5B—N4B—C3B—C16B	−9.2 (3)
C9A—N4A—C3A—C16A	−170.96 (18)	C9B—N4B—C3B—C16B	174.70 (18)
C9A—N4A—C5A—C6A	2.0 (3)	C9B—N4B—C5B—C6B	−1.4 (3)
C3A—N4A—C5A—C6A	176.94 (19)	C3B—N4B—C5B—C6B	−177.2 (2)
N4A—C5A—C6A—C7A	−0.1 (3)	N4B—C5B—C6B—C7B	0.0 (3)
C24A—N23A—C7A—C8A	−179.3 (2)	C24B—N23B—C7B—C8B	−180.0 (2)
C25A—N23A—C7A—C8A	−1.2 (3)	C25B—N23B—C7B—C8B	4.6 (3)
C24A—N23A—C7A—C6A	0.5 (3)	C24B—N23B—C7B—C6B	0.7 (3)
C25A—N23A—C7A—C6A	178.5 (2)	C25B—N23B—C7B—C6B	−174.8 (2)
C5A—C6A—C7A—N23A	178.7 (2)	C5B—C6B—C7B—N23B	−179.43 (19)
C5A—C6A—C7A—C8A	−1.6 (3)	C5B—C6B—C7B—C8B	1.2 (3)
N23A—C7A—C8A—C9A	−178.85 (19)	N23B—C7B—C8B—C9B	179.55 (19)
C6A—C7A—C8A—C9A	1.4 (3)	C6B—C7B—C8B—C9B	−1.1 (3)
C5A—N4A—C9A—C8A	−2.1 (3)	C7B—C8B—C9B—N4B	−0.2 (3)
C3A—N4A—C9A—C8A	−177.95 (16)	C7B—C8B—C9B—C1B	178.8 (2)
C5A—N4A—C9A—C1A	177.18 (17)	C5B—N4B—C9B—C8B	1.5 (3)
C3A—N4A—C9A—C1A	1.4 (2)	C3B—N4B—C9B—C8B	177.96 (17)
C7A—C8A—C9A—N4A	0.4 (3)	C5B—N4B—C9B—C1B	−177.80 (17)
C7A—C8A—C9A—C1A	−178.7 (2)	C3B—N4B—C9B—C1B	−1.3 (2)
C2A—C1A—C9A—N4A	−1.5 (2)	C2B—C1B—C9B—C8B	−177.8 (2)
C10A—C1A—C9A—N4A	172.80 (18)	C10B—C1B—C9B—C8B	6.2 (4)
C2A—C1A—C9A—C8A	177.6 (2)	C2B—C1B—C9B—N4B	1.4 (2)
C10A—C1A—C9A—C8A	−8.0 (4)	C10B—C1B—C9B—N4B	−174.66 (19)
C12A—O11A—C10A—O10A	−1.9 (3)	C12B—O11B—C10B—O10B	3.0 (3)
C12A—O11A—C10A—C1A	178.97 (18)	C12B—O11B—C10B—C1B	−178.1 (2)
C2A—C1A—C10A—O10A	−2.0 (3)	C2B—C1B—C10B—O10B	−1.8 (4)
C9A—C1A—C10A—O10A	−175.4 (2)	C9B—C1B—C10B—O10B	173.6 (2)
C2A—C1A—C10A—O11A	177.20 (17)	C2B—C1B—C10B—O11B	179.33 (18)
C9A—C1A—C10A—O11A	3.7 (3)	C9B—C1B—C10B—O11B	−5.3 (3)
C15A—O14A—C13A—O13A	3.0 (3)	C15B—O14B—C13B—O13B	−0.2 (3)
C15A—O14A—C13A—C2A	−176.34 (19)	C15B—O14B—C13B—C2B	179.8 (2)
C3A—C2A—C13A—O13A	72.0 (3)	C3B—C2B—C13B—O13B	−71.4 (3)
C1A—C2A—C13A—O13A	−102.6 (3)	C1B—C2B—C13B—O13B	102.0 (3)
C3A—C2A—C13A—O14A	−108.7 (2)	C3B—C2B—C13B—O14B	108.6 (2)
C1A—C2A—C13A—O14A	76.7 (2)	C1B—C2B—C13B—O14B	−78.0 (3)
C2A—C3A—C16A—O16A	−147.3 (2)	C2B—C3B—C16B—O16B	152.9 (2)
N4A—C3A—C16A—O16A	20.2 (3)	N4B—C3B—C16B—O16B	−19.2 (3)
C2A—C3A—C16A—C17A	32.2 (3)	C2B—C3B—C16B—C17B	−27.6 (4)
N4A—C3A—C16A—C17A	−160.31 (18)	N4B—C3B—C16B—C17B	160.24 (18)
O16A—C16A—C17A—C18A	−143.4 (2)	O16B—C16B—C17B—C18B	139.1 (2)
C3A—C16A—C17A—C18A	37.1 (3)	C3B—C16B—C17B—C18B	−40.4 (3)
O16A—C16A—C17A—C22A	33.8 (3)	O16B—C16B—C17B—C22B	−35.5 (3)
C3A—C16A—C17A—C22A	−145.7 (2)	C3B—C16B—C17B—C22B	145.1 (2)
C22A—C17A—C18A—C19A	0.5 (3)	C22B—C17B—C18B—C19B	−0.6 (3)
C16A—C17A—C18A—C19A	177.7 (2)	C16B—C17B—C18B—C19B	−175.2 (2)
C17A—C18A—C19A—C20A	1.1 (4)	C17B—C18B—C19B—C20B	−1.4 (4)
C18A—C19A—C20A—C21A	−1.4 (4)	C18B—C19B—C20B—C21B	2.0 (4)
C18A—C19A—C20A—C26A	−178.9 (2)	C18B—C19B—C20B—C26B	−178.9 (2)
C19A—C20A—C21A—C22A	0.0 (4)	C19B—C20B—C21B—C22B	−0.7 (3)
C26A—C20A—C21A—C22A	177.5 (2)	C26B—C20B—C21B—C22B	−179.7 (2)
C20A—C21A—C22A—C17A	1.7 (4)	C20B—C21B—C22B—C17B	−1.3 (3)
C18A—C17A—C22A—C21A	−1.9 (3)	C18B—C17B—C22B—C21B	1.9 (3)
C16A—C17A—C22A—C21A	−179.2 (2)	C16B—C17B—C22B—C21B	176.73 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5B—H52···O16Bⁱ	0.93	2.45	3.154 (3)	132
C15B—H155···O10Bⁱⁱ	0.96	2.52	3.417 (4)	156
C25B—H256···O16Aⁱⁱⁱ	0.96	2.60	3.531 (4)	164

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

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Di­methyl 7-(N,N-di­methyl­amino)-3-(4-methyl­benzoyl)­indolizine-1,2-di­carboxyl­ate

Supporting information

Key indicators

checkCIF/PLATON results

Dimethyl 7-(N,N-dimethylamino)-3-(4-methylbenzoyl)indolizine-1,2-dicarboxylate