Download citation
Download citation
link to html
The structure of the title compound, C30H33N3O10, consists of an almost planar imidazolin-2-one system connecting two planar substituted phenyl groups and a roughly planar 3,4,5-trimethoxy­anilinocarbonyl fragment which forms a dihedral angle of 95.17 (9)° with the heterocyclic ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805042005/jh6031sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805042005/jh6031Isup2.hkl
Contains datablock I

CCDC reference: 296596

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.057
  • wR factor = 0.131
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O6 - C20 .. 11.13 su PLAT230_ALERT_2_B Hirshfeld Test Diff for O10 - C30 .. 7.64 su
Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.660 Test value = 0.600 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.66 e/A   3 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.90 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O5 - C15 .. 5.80 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C16 - C17 .. 5.78 su
0 ALERT level A = In general: serious problem 2 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 7 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

Comment top

Imidazolones, in particular aryl-substituted imidazolin-2-ones, have become attractive targets for organic synthesis because of their broad spectrum of biological activities, being reported as antioxidants (Smith et al., 1987), ATP-sensitive potassium channel openers (Gadwood et al., 1995) and anti-inflammatory phosphodiesterse PDE4 inhibitors (Andrés et al., 2002). Additionally, they are widely used in combinatorial chemistry to search for pharmacologically active agents (Durant, 1985). In order to study their potential biological activity in other areas, a series of imidazolin-2-ones have been synthesized and evaluated for antitumour activity in vitro against a human tumour cell line (leukaemia HL-60). The title compound, (I), has a low micromolar IC50 of 6.5 µmol l−1 against leukaemia HL-60. To confirm its conformation in the crystal, an X-ray study of (I) has been carried out and the results are presented here (Fig. 1 and Table 1).

The roughly coplanar arrangement of the imidazolin-2-one and carboxamide groups may be further stabilized by an intramolecular N1—H1···O2 contact (H1···O2 = 1.97 Å and N1—H1···O2 = 142°).

Experimental top

3,4,5-Trimethoxyaniline (3 mmol) in dry toluene (4 ml) was added dropwise to a stirred solution of (COCl2)3 (2.91 mmol) in dry toluene (4 ml) and cooled in an ice bath. After stirring for 1 h at room temperature and refluxing for 4 h, 3,4-dimethoxy-ω-aminoacetophenone (3 mmol) was added to the mixture directly and it was then heated under reflux overnight. After removal of the toluene, the residue was extracted with dichloromethane and dried over anhydrous sodium sulfate. After removing the solvent in vacuo, the residue was purified by column chromatography (silica gel, trichloromethane–petroleum ether = 1:1) to afford the title compound. Crystals of (I) suitable for crystallographic study were obtained by slow crystallization from ethyl acetate at room temperature.

Refinement top

All H atoms were positioned geometrically. The methyl H atoms were then constrained to an ideal geometry, with C—H = 0.96 Å and Uiso(H) = 1.2Ueq(C), but each group was allowed to rotate freely about its C—C bond. All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.98 Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: Please provide missing information; software used to prepare material for publication: CrystalStructure.

Figures top
[Figure 1] Fig. 1. A view of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 40% probability level.
4-(3,4-Dimethoxyphenyl)-2-oxo-N,3-bis(3,4,5-trimethoxyphenyl)- 2,3-dihydro-1H-imidazoline-1-carboxamide top
Crystal data top
C30H33N3O10Z = 2
Mr = 595.60F(000) = 628.00
Triclinic, P1Dx = 1.337 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71075 Å
a = 9.429 (4) ÅCell parameters from 11137 reflections
b = 11.209 (4) Åθ = 3.0–27.5°
c = 15.890 (7) ŵ = 0.10 mm1
α = 93.802 (15)°T = 296 K
β = 104.333 (16)°Platelet, colourless
γ = 112.476 (14)°0.33 × 0.20 × 0.10 mm
V = 1479.1 (10) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4056 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.027
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1212
Tmin = 0.961, Tmax = 0.990k = 1413
14714 measured reflectionsl = 2020
6711 independent reflections
Refinement top
Refinement on F2 w = 1/[0.0002Fo2 + 3σ(Fo2) + 0.5]/(4Fo2)
R[F2 > 2σ(F2)] = 0.057(Δ/σ)max < 0.001
wR(F2) = 0.131Δρmax = 0.66 e Å3
S = 1.01Δρmin = 0.54 e Å3
6711 reflectionsExtinction correction: Larson (1970), equation 22
440 parametersExtinction coefficient: 391 (28)
H-atom parameters constrained
Crystal data top
C30H33N3O10γ = 112.476 (14)°
Mr = 595.60V = 1479.1 (10) Å3
Triclinic, P1Z = 2
a = 9.429 (4) ÅMo Kα radiation
b = 11.209 (4) ŵ = 0.10 mm1
c = 15.890 (7) ÅT = 296 K
α = 93.802 (15)°0.33 × 0.20 × 0.10 mm
β = 104.333 (16)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
6711 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
4056 reflections with F2 > 2σ(F2)
Tmin = 0.961, Tmax = 0.990Rint = 0.027
14714 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.057440 parameters
wR(F2) = 0.131H-atom parameters constrained
S = 1.01Δρmax = 0.66 e Å3
6711 reflectionsΔρmin = 0.54 e Å3
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O11.19868 (18)0.32905 (13)0.56873 (9)0.0559 (4)
O20.73770 (18)0.19091 (14)0.38843 (10)0.0576 (4)
O31.2779 (2)0.90176 (17)0.19154 (12)0.0760 (6)
O41.0331 (2)0.68805 (19)0.09811 (11)0.0908 (6)
O50.4105 (2)0.46062 (18)0.18159 (12)0.0712 (6)
O60.3721 (2)0.30681 (17)0.03581 (11)0.0712 (5)
O70.5696 (2)0.18927 (17)0.02900 (10)0.0685 (5)
O80.70884 (19)0.25109 (14)0.61772 (11)0.0639 (5)
O90.9730 (2)0.19225 (16)0.75159 (11)0.0667 (5)
O101.2234 (2)0.03984 (17)0.78497 (11)0.0715 (5)
N10.9495 (2)0.15864 (16)0.52388 (11)0.0447 (5)
N21.0086 (2)0.33408 (16)0.45135 (10)0.0428 (4)
N30.8696 (2)0.37810 (16)0.33520 (10)0.0420 (4)
C11.0624 (2)0.2741 (2)0.52057 (12)0.0422 (6)
C21.1096 (2)0.4484 (2)0.43102 (12)0.0456 (5)
C31.0268 (2)0.47807 (19)0.36002 (12)0.0407 (5)
C40.8567 (2)0.2890 (2)0.39046 (12)0.0432 (6)
C51.0863 (2)0.5892 (2)0.31574 (12)0.0413 (5)
C61.2124 (2)0.7034 (2)0.36410 (13)0.0486 (6)
C71.2799 (2)0.8085 (2)0.32495 (16)0.0547 (6)
C81.2217 (2)0.8035 (2)0.23630 (16)0.0527 (7)
C91.0912 (2)0.6899 (2)0.18645 (16)0.0626 (7)
C101.0266 (2)0.5851 (2)0.22596 (14)0.0570 (6)
C111.4037 (4)1.0214 (2)0.2415 (2)0.0897 (10)
C120.8992 (6)0.5722 (4)0.0447 (2)0.1147 (18)
C130.7373 (2)0.35873 (19)0.25816 (12)0.0397 (5)
C140.6402 (2)0.4216 (2)0.26230 (13)0.0465 (6)
C150.5145 (2)0.4022 (2)0.18630 (16)0.0496 (6)
C160.4927 (2)0.3229 (2)0.10944 (14)0.0507 (6)
C170.5968 (2)0.2624 (2)0.10780 (13)0.0486 (6)
C180.7176 (2)0.2779 (2)0.18322 (12)0.0433 (5)
C190.4076 (3)0.5238 (2)0.2614 (2)0.0817 (10)
C200.2443 (5)0.1699 (4)0.0024 (3)0.0955 (18)
C210.6837 (3)0.1408 (2)0.02096 (17)0.0823 (10)
C220.9599 (2)0.0747 (2)0.58456 (12)0.0431 (6)
C230.8296 (2)0.0436 (2)0.56983 (13)0.0471 (6)
C240.8318 (2)0.1316 (2)0.62617 (13)0.0477 (6)
C250.9683 (2)0.1018 (2)0.69772 (13)0.0487 (6)
C261.0966 (2)0.0175 (2)0.71245 (13)0.0502 (6)
C271.0968 (2)0.1068 (2)0.65609 (12)0.0497 (6)
C280.5643 (2)0.2853 (2)0.54888 (17)0.0734 (8)
C290.9108 (3)0.1828 (2)0.82290 (19)0.0836 (10)
C301.3567 (3)0.1639 (2)0.80529 (18)0.0929 (10)
H10.85880.13260.48370.053*
H21.21730.49710.46190.050*
H61.25350.70940.42460.057*
H71.36640.88380.35910.063*
H100.94100.50950.19170.061*
H140.65640.47550.31400.057*
H180.78450.23480.18330.051*
H230.73940.06410.52170.057*
H271.18510.18660.66600.057*
H1111.37181.05260.28830.108*
H1121.49841.00720.26620.108*
H1131.42591.08550.20390.108*
H1210.81110.55820.06840.113*
H1220.86930.58370.01550.113*
H1230.92560.49760.04690.113*
H1910.34460.57390.24840.109*
H1920.36140.45860.29450.110*
H1930.51550.58110.29540.110*
H2010.25520.11740.04690.109*
H2020.14010.17140.01030.109*
H2030.25610.13290.05030.110*
H2110.69670.08980.06610.097*
H2120.78460.21300.02760.097*
H2130.64790.08670.03600.096*
H2810.48760.36990.55160.081*
H2820.52220.22090.55600.081*
H2830.58490.28780.49270.081*
H2910.97010.09680.85860.104*
H2920.91960.24740.85820.104*
H2930.79990.19820.80010.104*
H3011.43000.17230.86170.097*
H3021.41060.17110.76070.098*
H3031.31930.23230.80720.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0499 (9)0.0583 (9)0.0450 (8)0.0169 (7)0.0027 (7)0.0114 (7)
O20.0410 (9)0.0623 (9)0.0571 (9)0.0117 (8)0.0052 (7)0.0261 (7)
O30.0821 (13)0.0623 (10)0.0745 (11)0.0121 (10)0.0320 (10)0.0291 (9)
O40.0840 (14)0.0860 (13)0.0556 (11)0.0036 (11)0.0014 (9)0.0326 (10)
O50.0610 (11)0.0940 (13)0.0809 (12)0.0491 (10)0.0257 (9)0.0357 (10)
O60.0517 (10)0.0787 (11)0.0612 (10)0.0182 (9)0.0098 (8)0.0250 (9)
O70.0642 (11)0.0854 (12)0.0424 (9)0.0282 (10)0.0003 (8)0.0007 (8)
O80.0532 (10)0.0604 (10)0.0679 (11)0.0168 (8)0.0085 (8)0.0230 (8)
O90.0706 (11)0.0725 (11)0.0678 (11)0.0384 (9)0.0184 (9)0.0360 (9)
O100.0624 (11)0.0773 (11)0.0541 (9)0.0191 (9)0.0059 (8)0.0256 (8)
N10.0410 (10)0.0543 (10)0.0369 (9)0.0210 (9)0.0045 (8)0.0134 (8)
N20.0409 (10)0.0477 (10)0.0352 (9)0.0167 (8)0.0053 (7)0.0110 (7)
N30.0377 (9)0.0480 (9)0.0365 (9)0.0160 (8)0.0061 (7)0.0122 (7)
C10.0462 (13)0.0498 (12)0.0333 (10)0.0254 (11)0.0068 (9)0.0079 (9)
C20.0409 (12)0.0438 (11)0.0420 (11)0.0118 (10)0.0047 (9)0.0069 (9)
C30.0352 (11)0.0448 (11)0.0386 (11)0.0161 (9)0.0060 (9)0.0065 (9)
C40.0413 (12)0.0517 (12)0.0372 (11)0.0218 (11)0.0075 (9)0.0118 (9)
C50.0356 (11)0.0471 (11)0.0437 (11)0.0197 (9)0.0110 (9)0.0112 (9)
C60.0486 (13)0.0506 (12)0.0435 (12)0.0205 (11)0.0081 (10)0.0084 (10)
C70.0516 (14)0.0459 (12)0.0594 (14)0.0137 (11)0.0151 (11)0.0072 (11)
C80.0487 (13)0.0522 (13)0.0602 (14)0.0179 (11)0.0232 (11)0.0212 (11)
C90.0545 (15)0.0753 (16)0.0481 (13)0.0161 (13)0.0122 (11)0.0254 (12)
C100.0453 (13)0.0592 (14)0.0464 (13)0.0053 (11)0.0047 (10)0.0134 (11)
C110.112 (2)0.0546 (16)0.102 (2)0.0179 (16)0.0545 (19)0.0259 (15)
C120.122 (4)0.109 (4)0.050 (2)0.004 (3)0.016 (2)0.033 (2)
C130.0323 (10)0.0455 (11)0.0392 (11)0.0154 (9)0.0062 (8)0.0149 (9)
C140.0447 (12)0.0498 (12)0.0467 (12)0.0188 (10)0.0155 (10)0.0154 (10)
C150.0355 (11)0.0585 (13)0.0654 (15)0.0256 (10)0.0177 (10)0.0311 (11)
C160.0352 (11)0.0654 (14)0.0475 (13)0.0186 (11)0.0050 (10)0.0254 (11)
C170.0446 (12)0.0503 (12)0.0382 (11)0.0095 (10)0.0065 (9)0.0112 (10)
C180.0384 (11)0.0466 (11)0.0436 (11)0.0176 (9)0.0080 (9)0.0147 (9)
C190.077 (2)0.087 (2)0.110 (2)0.0540 (17)0.0399 (18)0.0313 (17)
C200.077 (3)0.125 (4)0.069 (3)0.037 (3)0.005 (2)0.004 (3)
C210.085 (2)0.098 (2)0.0576 (16)0.0351 (19)0.0188 (15)0.0027 (15)
C220.0478 (12)0.0525 (12)0.0360 (10)0.0277 (11)0.0117 (9)0.0119 (9)
C230.0411 (12)0.0592 (13)0.0411 (11)0.0240 (11)0.0062 (9)0.0110 (10)
C240.0472 (13)0.0500 (12)0.0485 (12)0.0214 (11)0.0158 (10)0.0118 (10)
C250.0524 (13)0.0574 (13)0.0467 (12)0.0315 (11)0.0152 (10)0.0206 (10)
C260.0489 (13)0.0655 (14)0.0385 (11)0.0298 (12)0.0054 (10)0.0147 (10)
C270.0486 (13)0.0556 (13)0.0399 (11)0.0201 (11)0.0058 (10)0.0125 (10)
C280.0534 (16)0.0740 (17)0.0738 (18)0.0124 (13)0.0083 (13)0.0162 (14)
C290.080 (2)0.107 (2)0.0736 (19)0.0409 (18)0.0252 (16)0.0494 (17)
C300.0692 (19)0.105 (2)0.0700 (18)0.0207 (17)0.0165 (15)0.0248 (16)
Geometric parameters (Å, º) top
O1—C11.209 (2)C22—C231.376 (2)
O2—C41.226 (2)C22—C271.397 (2)
O3—C81.358 (3)C23—C241.377 (3)
O3—C111.419 (2)C24—C251.399 (2)
O4—C91.370 (2)C25—C261.374 (2)
O4—C121.439 (4)C26—C271.387 (3)
O5—C151.362 (3)N1—H10.860
O5—C191.422 (4)C2—H20.930
O6—C161.360 (2)C6—H60.930
O6—C201.500 (4)C7—H70.930
O7—C171.360 (2)C10—H100.930
O7—C211.405 (4)C11—H1110.960
O8—C241.367 (2)C11—H1120.960
O8—C281.417 (2)C11—H1130.960
O9—C251.376 (3)C12—H1210.959
O9—C291.414 (4)C12—H1220.961
O10—C261.367 (2)C12—H1230.960
O10—C301.422 (2)C14—H140.930
N1—C11.339 (2)C18—H180.930
N1—C221.403 (2)C19—H1910.960
N2—C11.415 (2)C19—H1920.960
N2—C21.388 (2)C19—H1930.960
N2—C41.392 (2)C20—H2010.960
N3—C31.411 (2)C20—H2020.960
N3—C41.364 (2)C20—H2030.960
N3—C131.450 (2)C21—H2110.960
C2—C31.344 (3)C21—H2120.960
C3—C51.462 (2)C21—H2130.960
C5—C61.377 (2)C23—H230.930
C5—C101.389 (3)C27—H270.930
C6—C71.379 (3)C28—H2810.960
C7—C81.368 (3)C28—H2820.960
C8—C91.396 (2)C28—H2830.960
C9—C101.372 (3)C29—H2910.960
C13—C141.363 (3)C29—H2920.960
C13—C181.375 (3)C29—H2930.960
C14—C151.404 (2)C30—H3010.960
C15—C161.384 (3)C30—H3020.960
C16—C171.394 (4)C30—H3030.960
C17—C181.381 (2)
O1···O8i3.438 (2)H18···H113iii3.262
O1···C14ii3.327 (2)H18···H291i3.399
O1···C24i3.569 (2)H18···H292i2.976
O1···C28i3.393 (3)H23···O1i3.522
O2···C11iii3.190 (2)H23···H7ii3.261
O3···C21iv3.505 (3)H23···H27i3.541
O5···C29v3.396 (3)H23···H111ii3.442
O6···C12vi3.359 (6)H27···H14ii3.457
O7···C21vii3.455 (3)H27···H23i3.541
O7···C30viii3.556 (3)H27···H193ii2.905
O8···O1i3.438 (2)H111···O2x3.115
O8···N2i3.518 (2)H111···O8ii3.029
O8···C1i3.499 (3)H111···C23ii3.271
O8···C2i3.427 (3)H111···C24ii2.957
O9···N2i3.573 (2)H111···C25ii3.511
O9···N3i3.382 (3)H111···C28ii3.315
O9···C3i3.558 (3)H111···H23ii3.442
O9···C4i3.413 (3)H111···H282ii2.719
O9···C18i3.359 (3)H111···H293ii2.909
O10···C20ix3.588 (5)H112···O2x2.618
N1···C6ii3.267 (3)H112···O10xi3.143
N1···C22i3.518 (3)H112···C18x3.508
N1···C23i3.399 (3)H112···C30xi3.053
N1···C24i3.584 (3)H112···H18x3.531
N2···O8i3.518 (2)H112···H213iv3.502
N2···O9i3.573 (2)H112···H301xi3.131
N2···C24i3.478 (3)H112···H302xi2.508
N2···C25i3.508 (3)H113···O2x3.354
N3···O9i3.382 (3)H113···O7x3.464
C1···O8i3.499 (3)H113···C13x3.204
C1···C6ii3.596 (3)H113···C14x3.453
C1···C23i3.466 (3)H113···C15x3.370
C1···C24i3.295 (3)H113···C16x3.074
C2···O8i3.427 (3)H113···C17x2.835
C3···O9i3.558 (3)H113···C18x2.886
C4···O9i3.413 (3)H113···H18x3.262
C4···C25i3.534 (4)H113···H201x2.741
C6···N1ii3.267 (3)H113···H213iv2.949
C6···C1ii3.596 (3)H113···H293ii2.852
C7···C22ii3.538 (4)H121···O6vi2.989
C11···O2x3.190 (2)H121···C20vi3.494
C12···O6vi3.359 (6)H121···H202vi3.125
C12···C12iv3.411 (9)H122···O5vi3.090
C14···O1ii3.327 (2)H122···O6vi2.936
C18···O9i3.359 (3)H122···C12iv3.368
C20···O10viii3.588 (5)H122···C20vi3.334
C20···C29v3.462 (6)H122···H122iv3.591
C20···C30viii3.551 (6)H122···H123iv2.566
C21···O3iv3.505 (3)H122···H202vi2.786
C21···O7vii3.455 (3)H122···H212iv3.249
C21···C21vii3.553 (3)H122···H292xiii2.850
C22···N1i3.518 (3)H123···O4iv3.197
C22···C7ii3.538 (4)H123···C12iv2.737
C22···C22i3.460 (3)H123···H122iv2.566
C22···C23i3.593 (3)H123···H123iv2.277
C23···N1i3.399 (3)H191···C5xiv2.948
C23···C1i3.466 (3)H191···C6xiv3.034
C23···C22i3.593 (3)H191···C7xiv3.152
C24···O1i3.569 (2)H191···C8xiv3.199
C24···N1i3.584 (3)H191···C9xiv3.122
C24···N2i3.478 (3)H191···C10xiv2.983
C24···C1i3.295 (3)H191···C30ii3.534
C25···N2i3.508 (3)H191···H6xiv3.536
C25···C4i3.534 (4)H191···H10xiv3.454
C28···O1i3.393 (3)H191···H292v3.548
C29···O5v3.396 (3)H191···H302ii2.949
C29···C20v3.462 (6)H191···H303ii3.453
C30···O7ix3.556 (3)H192···O8v2.739
C30···C20ix3.551 (6)H192···O9v3.281
O1···H14ii2.459H192···C2xiv3.568
O1···H23i3.522H192···C5xiv3.501
O1···H193ii2.774H192···C28v3.358
O1···H281x3.513H192···C29v3.229
O1···H283i2.642H192···H2xiv3.345
O2···H6ii3.074H192···H281v2.945
O2···H111iii3.115H192···H292v3.126
O2···H112iii2.618H192···H293v2.826
O2···H113iii3.354H193···O1ii2.774
O2···H282v2.925H193···C30ii3.333
O3···H201x3.473H193···H27ii2.905
O3···H212iv3.455H193···H281v3.502
O3···H213iv2.727H193···H283xv3.172
O3···H301xi3.435H193···H302ii2.855
O3···H302xi3.268H193···H303ii2.946
O4···H123iv3.197H201···O3iii3.473
O4···H202vi2.868H201···C11iii3.483
O4···H212iv2.952H201···C21vii3.323
O4···H213iv3.519H201···C29v3.091
O5···H122vi3.090H201···H113iii2.741
O5···H292v2.990H201···H211vii3.078
O5···H293v2.934H201···H213vii2.779
O5···H303ii3.370H201···H291viii3.475
O6···H121vi2.989H201···H291v2.841
O6···H122vi2.936H201···H292v3.145
O6···H292v3.448H201···H293v2.774
O6···H293v3.452H202···O4vi2.868
O6···H301viii3.324H202···C12vi3.101
O6···H303viii3.539H202···C29v3.133
O7···H113iii3.464H202···H121vi3.125
O7···H211vii3.140H202···H122vi2.786
O7···H213vii3.016H202···H291viii3.128
O7···H301viii2.617H202···H291v2.904
O8···H2i3.336H202···H292v2.766
O8···H111ii3.029H202···H293v3.220
O8···H192v2.739H203···O10viii2.650
O9···H18i2.501H203···C21vii3.369
O9···H192v3.281H203···C30viii2.686
O9···H211i3.431H203···H211vii2.704
O10···H18i3.129H203···H213vii3.210
O10···H112xi3.143H203···H291viii2.875
O10···H203ix2.650H203···H301viii2.345
O10···H211i2.948H203···H303viii2.686
N1···H6ii3.050H211···O7vii3.140
N2···H6ii3.443H211···O9i3.431
C1···H6ii3.370H211···O10i2.948
C1···H14ii3.420H211···C20vii3.329
C1···H283i3.329H211···C21vii3.382
C2···H192xii3.568H211···C29i3.387
C2···H281x3.328H211···C30i3.564
C4···H6ii3.353H211···H201vii3.078
C5···H191xii2.948H211···H203vii2.704
C5···H192xii3.501H211···H211vii3.478
C6···H1ii3.292H211···H213vii2.982
C6···H191xii3.034H211···H291i3.041
C6···H282x3.450H211···H292i3.215
C6···H283x3.561H211···H301i3.133
C7···H191xii3.152H212···O3iv3.455
C7···H302xi3.453H212···O4iv2.952
C8···H191xii3.199H212···C12iv3.547
C8···H302xi3.357H212···C29i3.388
C9···H191xii3.122H212···H122iv3.249
C10···H191xii2.983H212···H291i3.296
C11···H201x3.483H212···H292i2.794
C11···H213iv3.257H212···H301viii3.557
C11···H282ii3.546H213···O3iv2.727
C11···H293ii3.241H213···O4iv3.519
C11···H302xi3.261H213···O7vii3.016
C12···H122iv3.368H213···C11iv3.257
C12···H123iv2.737H213···C20vii3.430
C12···H202vi3.101H213···C21vii3.270
C12···H212iv3.547H213···H112iv3.502
C13···H113iii3.204H213···H113iv2.949
C14···H113iii3.453H213···H201vii2.779
C14···H281v3.463H213···H203vii3.210
C15···H113iii3.370H213···H211vii2.982
C15···H293v3.043H213···H213vii3.256
C16···H113iii3.074H213···H301viii2.801
C16···H293v3.304H281···O1iii3.513
C17···H113iii2.835H281···C2iii3.328
C18···H112iii3.508H281···C14v3.463
C18···H113iii2.886H281···H2iii2.401
C19···H292v3.425H281···H6iii3.045
C19···H293v3.349H281···H14v2.890
C19···H302ii3.277H281···H192v2.945
C19···H303ii3.420H281···H193v3.502
C20···H121vi3.494H281···H2813.364
C20···H122vi3.334H282···O2v2.925
C20···H211vii3.329H282···C6iii3.450
C20···H213vii3.430H282···C11ii3.546
C20···H291viii3.332H282···H2iii3.284
C20···H291v3.290H282···H6iii2.654
C20···H292v3.243H282···H7iii3.586
C20···H293v3.277H282···H7ii3.576
C20···H301viii3.159H282···H111ii2.719
C20···H303viii3.407H283···O1i2.642
C21···H201vii3.323H283···C1i3.329
C21···H203vii3.369H283···C6iii3.561
C21···H211vii3.382H283···H2iii3.268
C21···H213vii3.270H283···H2i3.522
C21···H291i3.582H283···H6iii3.031
C21···H292i3.440H283···H193xvi3.172
C21···H301viii3.166H291···C20ix3.332
C22···H7ii3.590H291···C20v3.290
C23···H7ii3.346H291···C21i3.582
C23···H111ii3.271H291···H18i3.399
C24···H111ii2.957H291···H201ix3.475
C25···H18i3.476H291···H201v2.841
C25···H111ii3.511H291···H202ix3.128
C27···H1i3.583H291···H202v2.904
C28···H2iii3.127H291···H203ix2.875
C28···H6iii3.079H291···H211i3.041
C28···H111ii3.315H291···H212i3.296
C28···H192v3.358H292···O5v2.990
C29···H18i3.164H292···O6v3.448
C29···H192v3.229H292···C19v3.425
C29···H201v3.091H292···C20v3.243
C29···H202v3.133H292···C21i3.440
C29···H211i3.387H292···H18i2.976
C29···H212i3.388H292···H122xvii2.850
C30···H112xi3.053H292···H191v3.548
C30···H191ii3.534H292···H192v3.126
C30···H193ii3.333H292···H201v3.145
C30···H203ix2.686H292···H202v2.766
C30···H211i3.564H292···H211i3.215
H1···C6ii3.292H292···H212i2.794
H1···C27i3.583H293···O5v2.934
H1···H6ii2.870H293···O6v3.452
H2···O8i3.336H293···C11ii3.241
H2···C28x3.127H293···C15v3.043
H2···H14ii3.416H293···C16v3.304
H2···H192xii3.345H293···C19v3.349
H2···H281x2.401H293···C20v3.277
H2···H282x3.284H293···H111ii2.909
H2···H283x3.268H293···H113ii2.852
H2···H283i3.522H293···H192v2.826
H6···O2ii3.074H293···H201v2.774
H6···N1ii3.050H293···H202v3.220
H6···N2ii3.443H301···O3xi3.435
H6···C1ii3.370H301···O6ix3.324
H6···C4ii3.353H301···O7ix2.617
H6···C28x3.079H301···C20ix3.159
H6···H1ii2.870H301···C21ix3.166
H6···H191xii3.536H301···H112xi3.131
H6···H281x3.045H301···H203ix2.345
H6···H282x2.654H301···H211i3.133
H6···H283x3.031H301···H212ix3.557
H7···C22ii3.590H301···H213ix2.801
H7···C23ii3.346H302···O3xi3.268
H7···H23ii3.261H302···C7xi3.453
H7···H282x3.586H302···C8xi3.357
H7···H282ii3.576H302···C11xi3.261
H7···H302xi3.353H302···C19ii3.277
H10···H191xii3.454H302···H7xi3.353
H14···O1ii2.459H302···H112xi2.508
H14···C1ii3.420H302···H191ii2.949
H14···H2ii3.416H302···H193ii2.855
H14···H27ii3.457H303···O5ii3.370
H14···H281v2.890H303···O6ix3.539
H18···O9i2.501H303···C19ii3.420
H18···O10i3.129H303···C20ix3.407
H18···C25i3.476H303···H191ii3.453
H18···C29i3.164H303···H193ii2.946
H18···H112iii3.531H303···H203ix2.686
C8—O3—C11117.17 (19)C22—N1—H1115.7
C9—O4—C12118.9 (2)N2—C2—H2125.4
C15—O5—C19118.5 (2)C3—C2—H2125.3
C16—O6—C20116.0 (2)C5—C6—H6119.1
C17—O7—C21117.61 (18)C7—C6—H6119.2
C24—O8—C28118.10 (19)C6—C7—H7119.7
C25—O9—C29113.9 (2)C8—C7—H7119.5
C26—O10—C30117.6 (2)C5—C10—H10119.2
C1—N1—C22128.45 (16)C9—C10—H10119.1
C1—N2—C2122.81 (16)O3—C11—H111109.5
C1—N2—C4128.11 (16)O3—C11—H112109.4
C2—N2—C4108.97 (17)O3—C11—H113109.5
C3—N3—C4110.86 (16)H111—C11—H112109.5
C3—N3—C13127.65 (17)H111—C11—H113109.5
C4—N3—C13121.27 (14)H112—C11—H113109.5
O1—C1—N1127.7 (2)O4—C12—H121107.3
O1—C1—N2119.14 (17)O4—C12—H122110.7
N1—C1—N2113.15 (16)O4—C12—H123110.4
N2—C2—C3109.26 (16)H121—C12—H122109.5
N3—C3—C2105.86 (17)H121—C12—H123109.5
N3—C3—C5126.48 (17)H122—C12—H123109.4
C2—C3—C5127.65 (16)C13—C14—H14121.0
O2—C4—N2126.8 (2)C15—C14—H14121.0
O2—C4—N3128.10 (18)C13—C18—H18120.6
N2—C4—N3105.05 (15)C17—C18—H18120.6
C3—C5—C6119.01 (17)O5—C19—H191110.0
C3—C5—C10123.66 (15)O5—C19—H192109.2
C6—C5—C10117.29 (19)O5—C19—H193109.1
C5—C6—C7121.61 (19)H191—C19—H192109.5
C6—C7—C8120.81 (17)H191—C19—H193109.5
O3—C8—C7125.51 (17)H192—C19—H193109.5
O3—C8—C9116.0 (2)O6—C20—H201109.0
C7—C8—C9118.5 (2)O6—C20—H202109.8
O4—C9—C8117.4 (2)O6—C20—H203109.7
O4—C9—C10122.46 (18)H201—C20—H202109.5
C8—C9—C10120.1 (2)H201—C20—H203109.5
C5—C10—C9121.64 (17)H202—C20—H203109.4
N3—C13—C14119.39 (18)O7—C21—H211109.3
N3—C13—C18117.6 (2)O7—C21—H212109.4
C14—C13—C18122.99 (18)O7—C21—H213109.7
C13—C14—C15118.0 (2)H211—C21—H212109.5
O5—C15—C14123.7 (2)H211—C21—H213109.5
O5—C15—C16115.9 (2)H212—C21—H213109.5
C14—C15—C16120.4 (2)C22—C23—H23119.8
O6—C16—C15119.8 (2)C24—C23—H23119.9
O6—C16—C17120.6 (2)C22—C27—H27120.7
C15—C16—C17119.6 (2)C26—C27—H27121.0
O7—C17—C16115.70 (19)O8—C28—H281109.4
O7—C17—C18124.1 (2)O8—C28—H282109.1
C16—C17—C18120.2 (2)O8—C28—H283109.9
C13—C18—C17118.7 (2)H281—C28—H282109.5
N1—C22—C23117.07 (17)H281—C28—H283109.5
N1—C22—C27122.24 (17)H282—C28—H283109.5
C23—C22—C27120.7 (2)O9—C29—H291109.8
C22—C23—C24120.30 (18)O9—C29—H292109.5
O8—C24—C23124.95 (18)O9—C29—H293109.1
O8—C24—C25115.1 (2)H291—C29—H292109.5
C23—C24—C25119.94 (18)H291—C29—H293109.5
O9—C25—C24119.85 (17)H292—C29—H293109.5
O9—C25—C26120.99 (19)O10—C30—H301109.6
C24—C25—C26119.1 (2)O10—C30—H302109.5
O10—C26—C25115.3 (2)O10—C30—H303109.3
O10—C26—C27123.03 (17)H301—C30—H302109.5
C25—C26—C27121.62 (19)H301—C30—H303109.5
C22—C27—C26118.26 (18)H302—C30—H303109.5
C1—N1—H1115.9
C11—O3—C8—C72.5 (4)C2—C3—C5—C10149.1 (2)
C11—O3—C8—C9176.0 (2)C3—C5—C6—C7176.0 (2)
C12—O4—C9—C8179.7 (3)C3—C5—C10—C9176.9 (2)
C12—O4—C9—C100.1 (3)C6—C5—C10—C90.6 (4)
C19—O5—C15—C1412.8 (3)C10—C5—C6—C71.7 (4)
C19—O5—C15—C16168.9 (2)C5—C6—C7—C81.0 (4)
C20—O6—C16—C15116.8 (3)C6—C7—C8—O3179.1 (2)
C20—O6—C16—C1764.5 (3)C6—C7—C8—C90.7 (4)
C21—O7—C17—C16171.8 (2)O3—C8—C9—O40.2 (4)
C21—O7—C17—C188.6 (3)O3—C8—C9—C10179.7 (2)
C28—O8—C24—C233.6 (4)C7—C8—C9—O4178.8 (2)
C28—O8—C24—C25177.4 (2)C7—C8—C9—C101.7 (4)
C29—O9—C25—C2488.7 (2)O4—C9—C10—C5179.5 (2)
C29—O9—C25—C2692.0 (3)C8—C9—C10—C51.0 (4)
C30—O10—C26—C25177.5 (2)N3—C13—C14—C15179.18 (18)
C30—O10—C26—C273.6 (4)N3—C13—C18—C17177.22 (18)
C1—N1—C22—C23175.5 (2)C14—C13—C18—C171.9 (3)
C1—N1—C22—C273.1 (4)C18—C13—C14—C150.1 (2)
C22—N1—C1—O11.4 (4)C13—C14—C15—O5179.1 (2)
C22—N1—C1—N2178.4 (2)C13—C14—C15—C161.0 (3)
C1—N2—C2—C3177.0 (2)O5—C15—C16—O60.6 (3)
C2—N2—C1—O15.9 (3)O5—C15—C16—C17178.2 (2)
C2—N2—C1—N1174.3 (2)C14—C15—C16—O6178.9 (2)
C1—N2—C4—O24.1 (4)C14—C15—C16—C170.1 (3)
C1—N2—C4—N3176.7 (2)O6—C16—C17—O70.5 (3)
C4—N2—C1—O1178.4 (2)O6—C16—C17—C18179.14 (19)
C4—N2—C1—N11.4 (3)C15—C16—C17—O7178.2 (2)
C2—N2—C4—O2179.7 (2)C15—C16—C17—C182.1 (3)
C2—N2—C4—N30.5 (2)O7—C17—C18—C13177.42 (19)
C4—N2—C2—C30.6 (2)C16—C17—C18—C133.0 (3)
C3—N3—C4—O2179.4 (2)N1—C22—C23—C24179.4 (2)
C3—N3—C4—N20.2 (2)N1—C22—C27—C26179.7 (2)
C4—N3—C3—C20.2 (2)C23—C22—C27—C261.1 (4)
C4—N3—C3—C5179.1 (2)C27—C22—C23—C240.7 (4)
C3—N3—C13—C1487.0 (2)C22—C23—C24—O8179.7 (2)
C3—N3—C13—C1892.1 (2)C22—C23—C24—C251.3 (4)
C13—N3—C3—C2174.4 (2)O8—C24—C25—O92.0 (3)
C13—N3—C3—C54.5 (3)O8—C24—C25—C26178.7 (2)
C4—N3—C13—C1498.9 (2)C23—C24—C25—O9177.1 (2)
C4—N3—C13—C1882.0 (2)C23—C24—C25—C262.2 (4)
C13—N3—C4—O25.5 (4)O9—C25—C26—O102.3 (3)
C13—N3—C4—N2175.2 (2)O9—C25—C26—C27176.6 (2)
N2—C2—C3—N30.5 (2)C24—C25—C26—O10178.4 (2)
N2—C2—C3—C5179.4 (2)C24—C25—C26—C272.7 (4)
N3—C3—C5—C6152.9 (2)O10—C26—C27—C22179.1 (2)
N3—C3—C5—C1029.6 (4)C25—C26—C27—C222.1 (4)
C2—C3—C5—C628.4 (4)
Symmetry codes: (i) x+2, y, z+1; (ii) x+2, y+1, z+1; (iii) x1, y1, z; (iv) x+2, y+1, z; (v) x+1, y, z+1; (vi) x+1, y+1, z; (vii) x+1, y, z; (viii) x1, y, z1; (ix) x+1, y, z+1; (x) x+1, y+1, z; (xi) x+3, y+1, z+1; (xii) x+1, y, z; (xiii) x, y+1, z1; (xiv) x1, y, z; (xv) x, y+1, z; (xvi) x, y1, z; (xvii) x, y1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.861.972.698 (2)142

Experimental details

Crystal data
Chemical formulaC30H33N3O10
Mr595.60
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)9.429 (4), 11.209 (4), 15.890 (7)
α, β, γ (°)93.802 (15), 104.333 (16), 112.476 (14)
V3)1479.1 (10)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.33 × 0.20 × 0.10
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.961, 0.990
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
14714, 6711, 4056
Rint0.027
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.131, 1.01
No. of reflections6711
No. of parameters440
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.66, 0.54

Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, CrystalStructure (Rigaku/MSC & Rigaku, 2004), SIR97 (Altomare et al., 1999), CRYSTALS (Watkin et al., 1996), Please provide missing information, CrystalStructure.

 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds