Literature DB >> 26870486

Crystal structure of 4'-(2-meth-oxy-quinolin-3-yl)-1'-methyl-dispiro-[indan-2,2'-pyrrolidine-3',3''-indoline]-1,3,2''-trione.

Sadasivam Mathusalini1, Vijayan Viswanathan2, Palathurai Subramaniam Mohan1, Chia-Her Lin3, Devadasan Velmurugan2.   

Abstract

In the title compound, C30H23N3O4, the central 1-methyl-pyrrolidine ring adopts a twist conformation on the N-CH2 bond. The pyrrolidin-2-one ring of the indolin-2-one ring system also has a twist conformation on the C-C bond involving the spiro C atom and the carbonyl C atom. The five-membered ring of the indene-1,3-dione moiety has an envelope conformation with the spiro C atom as the flap. The quinoline ring system adopts an almost planar conformation (r.m.s. deviation = 0.04 Å). The mean planes of the indolin-2-one ring system, the indene-1,3-dione ring system and the the quinoline ring system are inclined to the mean plane of the central 1-methyl-pyrrolidine ring by 77.97 (7), 86.98 (7) and 46.58 (6)°, respectively. In the crystal, mol-ecules are linked via N-H⋯N hydrogen bonds, forming chains along the b axis. The chains are linked via a number of C-H⋯O hydrogen bonds, and C-H⋯π and π-π inter-actions [inter-centroid distance = 3.7404 (9) Å], forming a three-dimensional network.

Entities:  

Keywords:  crystal structure; hydrogen bonding; pyrrolidine; quinoline; spiro-indane; spiro-indolino

Year:  2015        PMID： 26870486      PMCID： PMC4719967          DOI： 10.1107/S2056989015023026

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


Related literature

For the biological activity of pyrrolidine and indole derivatives, see: Babu et al. (2012 ▸); Savithri et al. (2014 ▸); Govind et al. (2003 ▸); Gayathri et al. (2005 ▸); Li et al. (2004 ▸); Bellina & Rossi (2006 ▸). For the crystal structure of a similar di­spiro­indoline compound, see: Nirmala et al. (2009 ▸).

Experimental

Crystal data

C30H23N3O4 M = 489.51 Monoclinic, a = 10.9058 (3) Å b = 9.5178 (5) Å c = 23.8651 (6) Å β = 95.378 (2)° V = 2466.27 (16) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 293 K 0.27 × 0.18 × 0.11 mm

Data collection

Bruker SMART APEXII area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▸) T min = 0.976, T max = 0.990 23642 measured reflections 6134 independent reflections 4376 reflections with I > 2σ(I) R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.115 S = 1.03 6134 reflections 337 parameters H-atom parameters constrained Δρmax = 0.31 e Å−3 Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2008 ▸); cell refinement: SAINT (Bruker, 2008 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▸). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015023026/su5242sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015023026/su5242Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S2056989015023026/su5242Isup3.cml Click here for additional data file. . DOI: 10.1107/S2056989015023026/su5242fig1.tif The mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at 30% probability level. Click here for additional data file. c b- . DOI: 10.1107/S2056989015023026/su5242fig2.tif A partial view, along the c axis, of the crystal packing of the title compound, illustrating the formation of the hydrogen-bonded zigzag chains (dashed lines; see Table 1) running along the the b-axis direction. C-bound H atoms have been omitted for clarity. Click here for additional data file. b . DOI: 10.1107/S2056989015023026/su5242fig3.tif A view along the b axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines and C—H⋯π inter­actions as blue arrows (see Table 1). H atoms not involved in these inter­actions have been omitted for clarity. CCDC reference: 1439764 Additional supporting information: crystallographic information; 3D view; checkCIF report
C30H23N3O4F(000) = 1024
Mr = 489.51Dx = 1.318 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6134 reflections
a = 10.9058 (3) Åθ = 1.7–28.3°
b = 9.5178 (5) ŵ = 0.09 mm−1
c = 23.8651 (6) ÅT = 293 K
β = 95.378 (2)°Block, light yellow
V = 2466.27 (16) Å30.27 × 0.18 × 0.11 mm
Z = 4
Bruker SMART APEXII area-detector diffractometer6134 independent reflections
Radiation source: fine-focus sealed tube4376 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
ω and φ scansθmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −14→14
Tmin = 0.976, Tmax = 0.990k = −10→12
23642 measured reflectionsl = −31→31
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.115w = 1/[σ2(Fo2) + (0.0518P)2 + 0.5577P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
6134 reflectionsΔρmax = 0.31 e Å−3
337 parametersΔρmin = −0.22 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0015 (5)
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.
xyzUiso*/Ueq
C10.20917 (13)0.33633 (15)0.40978 (6)0.0154 (3)
C20.25284 (13)0.41678 (15)0.45432 (6)0.0164 (3)
H20.32360.47010.45200.020*
C30.19148 (13)0.42037 (15)0.50442 (6)0.0176 (3)
C40.22810 (14)0.50968 (16)0.55041 (6)0.0214 (3)
H40.29760.56600.54950.026*
C50.16109 (15)0.51327 (18)0.59628 (6)0.0250 (4)
H50.18440.57360.62600.030*
C60.05752 (15)0.42652 (18)0.59859 (6)0.0261 (4)
H60.01290.42960.62990.031*
C70.02161 (14)0.33733 (17)0.55504 (6)0.0233 (3)
H7−0.04590.27870.55740.028*
C80.08663 (13)0.33397 (16)0.50662 (6)0.0191 (3)
C90.10099 (13)0.25475 (16)0.41718 (6)0.0176 (3)
C10−0.04213 (16)0.0851 (2)0.37798 (8)0.0343 (4)
H10A−0.01780.01860.40720.051*
H10B−0.06390.03600.34330.051*
H10C−0.11180.13780.38810.051*
C110.26420 (13)0.32928 (14)0.35404 (5)0.0145 (3)
H110.19880.35600.32500.017*
C120.37260 (13)0.42704 (15)0.34739 (6)0.0169 (3)
H12A0.34480.52130.33720.020*
H12B0.42780.43110.38170.020*
C130.54710 (14)0.42826 (17)0.28930 (6)0.0228 (3)
H13A0.60390.42840.32260.034*
H13B0.53050.52320.27730.034*
H13C0.58230.37750.25990.034*
C140.44003 (13)0.21185 (15)0.31502 (6)0.0154 (3)
C150.54468 (13)0.16447 (16)0.35943 (6)0.0189 (3)
C160.59196 (13)0.02809 (16)0.34030 (7)0.0226 (3)
C170.67272 (15)−0.06517 (18)0.36946 (8)0.0333 (4)
H170.7027−0.04880.40670.040*
C180.70682 (17)−0.18363 (19)0.34082 (10)0.0431 (5)
H180.7609−0.24780.35920.052*
C190.66172 (16)−0.20855 (19)0.28513 (10)0.0402 (5)
H190.6872−0.28840.26700.048*
C200.57999 (15)−0.11731 (18)0.25617 (8)0.0307 (4)
H200.5492−0.13490.21920.037*
C210.54552 (13)0.00257 (17)0.28481 (7)0.0222 (3)
C220.46541 (13)0.12011 (16)0.26393 (6)0.0193 (3)
C230.30953 (12)0.17946 (15)0.33795 (5)0.0138 (3)
C240.31584 (13)0.06063 (15)0.38042 (5)0.0148 (3)
C250.36072 (13)0.05524 (16)0.43670 (6)0.0178 (3)
H250.39450.13460.45490.021*
C260.35408 (14)−0.07186 (16)0.46557 (6)0.0218 (3)
H260.3829−0.07720.50340.026*
C270.30461 (14)−0.19003 (17)0.43797 (6)0.0236 (3)
H270.3018−0.27400.45780.028*
C280.25907 (14)−0.18660 (16)0.38152 (6)0.0211 (3)
H280.2263−0.26640.36330.025*
C290.26467 (13)−0.05929 (15)0.35366 (5)0.0162 (3)
C300.22483 (13)0.11534 (15)0.28885 (5)0.0156 (3)
N10.04388 (11)0.24888 (13)0.46238 (5)0.0198 (3)
N20.43214 (11)0.36056 (13)0.30155 (5)0.0161 (3)
N30.21780 (11)−0.02577 (13)0.29860 (5)0.0171 (3)
H30.1884−0.08620.27410.021*
O10.05853 (9)0.17940 (11)0.37099 (4)0.0226 (2)
O20.17649 (9)0.17942 (11)0.24841 (4)0.0201 (2)
O30.58400 (10)0.23063 (12)0.40066 (4)0.0262 (3)
O40.42980 (10)0.14597 (13)0.21553 (4)0.0287 (3)
U11U22U33U12U13U23
C10.0163 (7)0.0128 (7)0.0173 (6)0.0012 (6)0.0025 (5)0.0014 (5)
C20.0178 (7)0.0135 (7)0.0179 (6)−0.0001 (6)0.0017 (5)0.0010 (5)
C30.0208 (7)0.0148 (8)0.0173 (6)0.0045 (6)0.0027 (5)0.0022 (6)
C40.0256 (8)0.0183 (8)0.0201 (7)0.0041 (6)0.0009 (6)0.0004 (6)
C50.0320 (9)0.0257 (9)0.0169 (7)0.0120 (7)0.0002 (6)−0.0002 (6)
C60.0296 (9)0.0322 (10)0.0177 (7)0.0146 (7)0.0075 (6)0.0071 (7)
C70.0206 (8)0.0257 (9)0.0247 (7)0.0063 (7)0.0071 (6)0.0076 (7)
C80.0194 (7)0.0170 (8)0.0210 (7)0.0054 (6)0.0029 (6)0.0043 (6)
C90.0164 (7)0.0147 (8)0.0214 (7)0.0014 (6)0.0007 (5)−0.0006 (6)
C100.0297 (9)0.0328 (11)0.0407 (10)−0.0171 (8)0.0054 (7)−0.0098 (8)
C110.0166 (7)0.0112 (7)0.0153 (6)0.0011 (6)0.0001 (5)−0.0002 (5)
C120.0210 (7)0.0130 (7)0.0166 (6)−0.0021 (6)0.0010 (5)0.0001 (5)
C130.0219 (8)0.0217 (8)0.0252 (7)−0.0012 (6)0.0049 (6)0.0068 (6)
C140.0175 (7)0.0125 (7)0.0160 (6)0.0003 (6)0.0008 (5)0.0029 (5)
C150.0166 (7)0.0188 (8)0.0209 (7)−0.0035 (6)0.0000 (6)0.0071 (6)
C160.0144 (7)0.0175 (8)0.0358 (9)−0.0008 (6)0.0021 (6)0.0090 (7)
C170.0198 (8)0.0235 (9)0.0556 (11)−0.0004 (7)−0.0028 (8)0.0167 (8)
C180.0225 (9)0.0206 (10)0.0853 (16)0.0057 (8)0.0009 (9)0.0172 (10)
C190.0255 (9)0.0152 (9)0.0815 (15)0.0024 (7)0.0141 (9)0.0000 (9)
C200.0227 (8)0.0196 (9)0.0518 (11)−0.0001 (7)0.0142 (8)−0.0024 (8)
C210.0166 (7)0.0168 (8)0.0341 (8)0.0009 (6)0.0071 (6)0.0027 (6)
C220.0189 (7)0.0182 (8)0.0214 (7)0.0007 (6)0.0051 (6)−0.0002 (6)
C230.0159 (7)0.0123 (7)0.0129 (6)0.0008 (6)−0.0002 (5)−0.0001 (5)
C240.0160 (7)0.0121 (7)0.0163 (6)0.0011 (6)0.0017 (5)0.0015 (5)
C250.0208 (7)0.0158 (8)0.0162 (7)−0.0014 (6)−0.0016 (5)−0.0006 (6)
C260.0270 (8)0.0214 (8)0.0162 (7)−0.0009 (7)−0.0018 (6)0.0034 (6)
C270.0306 (8)0.0160 (8)0.0238 (8)−0.0020 (7)0.0008 (6)0.0068 (6)
C280.0260 (8)0.0137 (8)0.0235 (7)−0.0025 (6)0.0010 (6)−0.0003 (6)
C290.0173 (7)0.0168 (8)0.0145 (6)0.0003 (6)0.0014 (5)−0.0012 (5)
C300.0167 (7)0.0148 (7)0.0153 (6)0.0003 (6)0.0012 (5)−0.0016 (5)
N10.0187 (6)0.0178 (7)0.0232 (6)0.0007 (5)0.0036 (5)0.0015 (5)
N20.0188 (6)0.0135 (6)0.0162 (6)−0.0001 (5)0.0028 (5)0.0029 (5)
N30.0228 (6)0.0126 (6)0.0151 (6)−0.0012 (5)−0.0023 (5)−0.0037 (5)
O10.0193 (5)0.0224 (6)0.0261 (5)−0.0076 (5)0.0019 (4)−0.0057 (4)
O20.0247 (5)0.0189 (6)0.0153 (5)0.0011 (4)−0.0046 (4)0.0009 (4)
O30.0282 (6)0.0245 (6)0.0240 (5)−0.0073 (5)−0.0076 (4)0.0062 (5)
O40.0353 (6)0.0339 (7)0.0175 (5)0.0083 (5)0.0048 (5)−0.0010 (5)
C1—C21.3595 (19)C14—C221.5455 (19)
C1—C91.4370 (19)C14—C151.550 (2)
C1—C111.5112 (18)C14—C231.6019 (18)
C2—C31.4243 (18)C15—O31.2122 (18)
C2—H20.9300C15—C161.484 (2)
C3—C81.413 (2)C16—C171.390 (2)
C3—C41.416 (2)C16—C211.394 (2)
C4—C51.373 (2)C17—C181.387 (3)
C4—H40.9300C17—H170.9300
C5—C61.404 (2)C18—C191.394 (3)
C5—H50.9300C18—H180.9300
C6—C71.370 (2)C19—C201.382 (3)
C6—H60.9300C19—H190.9300
C7—C81.4117 (19)C20—C211.399 (2)
C7—H70.9300C20—H200.9300
C8—N11.3768 (19)C21—C221.477 (2)
C9—N11.2965 (18)C22—O41.2091 (17)
C9—O11.3595 (17)C23—C241.5159 (19)
C10—O11.4398 (19)C23—C301.5478 (19)
C10—H10A0.9600C24—C251.3867 (18)
C10—H10B0.9600C24—C291.398 (2)
C10—H10C0.9600C25—C261.397 (2)
C11—C121.5244 (19)C25—H250.9300
C11—C231.5686 (19)C26—C271.387 (2)
C11—H110.9800C26—H260.9300
C12—N21.4668 (17)C27—C281.392 (2)
C12—H12A0.9700C27—H270.9300
C12—H12B0.9700C28—C291.386 (2)
C13—N21.4633 (18)C28—H280.9300
C13—H13A0.9600C29—N31.4013 (17)
C13—H13B0.9600C30—O21.2191 (16)
C13—H13C0.9600C30—N31.3664 (19)
C14—N21.4521 (18)N3—H30.8600
C2—C1—C9116.09 (12)O3—C15—C14125.85 (14)
C2—C1—C11125.05 (13)C16—C15—C14107.38 (12)
C9—C1—C11118.85 (12)C17—C16—C21121.39 (16)
C1—C2—C3120.81 (13)C17—C16—C15128.78 (15)
C1—C2—H2119.6C21—C16—C15109.81 (13)
C3—C2—H2119.6C16—C17—C18117.31 (18)
C8—C3—C4119.40 (13)C16—C17—H17121.3
C8—C3—C2117.56 (13)C18—C17—H17121.3
C4—C3—C2123.00 (14)C17—C18—C19121.42 (17)
C5—C4—C3120.05 (15)C17—C18—H18119.3
C5—C4—H4120.0C19—C18—H18119.3
C3—C4—H4120.0C20—C19—C18121.55 (17)
C4—C5—C6120.47 (15)C20—C19—H19119.2
C4—C5—H5119.8C18—C19—H19119.2
C6—C5—H5119.8C19—C20—C21117.27 (17)
C7—C6—C5120.54 (14)C19—C20—H20121.4
C7—C6—H6119.7C21—C20—H20121.4
C5—C6—H6119.7C16—C21—C20121.04 (15)
C6—C7—C8120.34 (15)C16—C21—C22109.82 (13)
C6—C7—H7119.8C20—C21—C22129.08 (15)
C8—C7—H7119.8O4—C22—C21127.10 (14)
N1—C8—C3122.06 (12)O4—C22—C14124.99 (14)
N1—C8—C7118.75 (14)C21—C22—C14107.81 (12)
C3—C8—C7119.17 (14)C24—C23—C30101.44 (11)
N1—C9—O1119.89 (13)C24—C23—C11120.68 (11)
N1—C9—C1126.12 (13)C30—C23—C11111.36 (11)
O1—C9—C1113.99 (12)C24—C23—C14112.70 (11)
O1—C10—H10A109.5C30—C23—C14107.67 (10)
O1—C10—H10B109.5C11—C23—C14102.66 (11)
H10A—C10—H10B109.5C25—C24—C29120.11 (13)
O1—C10—H10C109.5C25—C24—C23131.68 (13)
H10A—C10—H10C109.5C29—C24—C23108.21 (11)
H10B—C10—H10C109.5C24—C25—C26118.66 (13)
C1—C11—C12116.13 (11)C24—C25—H25120.7
C1—C11—C23114.59 (11)C26—C25—H25120.7
C12—C11—C23105.31 (11)C27—C26—C25120.25 (13)
C1—C11—H11106.7C27—C26—H26119.9
C12—C11—H11106.7C25—C26—H26119.9
C23—C11—H11106.7C26—C27—C28121.89 (14)
N2—C12—C11102.48 (11)C26—C27—H27119.1
N2—C12—H12A111.3C28—C27—H27119.1
C11—C12—H12A111.3C29—C28—C27117.19 (14)
N2—C12—H12B111.3C29—C28—H28121.4
C11—C12—H12B111.3C27—C28—H28121.4
H12A—C12—H12B109.2C28—C29—C24121.88 (13)
N2—C13—H13A109.5C28—C29—N3128.32 (13)
N2—C13—H13B109.5C24—C29—N3109.71 (12)
H13A—C13—H13B109.5O2—C30—N3126.84 (13)
N2—C13—H13C109.5O2—C30—C23125.82 (13)
H13A—C13—H13C109.5N3—C30—C23107.32 (11)
H13B—C13—H13C109.5C9—N1—C8117.27 (13)
N2—C14—C22112.79 (11)C14—N2—C13116.06 (11)
N2—C14—C15117.35 (12)C14—N2—C12106.06 (10)
C22—C14—C15101.55 (11)C13—N2—C12113.99 (12)
N2—C14—C23103.12 (11)C30—N3—C29111.23 (11)
C22—C14—C23113.03 (11)C30—N3—H3124.4
C15—C14—C23109.34 (10)C29—N3—H3124.4
O3—C15—C16126.68 (14)C9—O1—C10116.13 (12)
C9—C1—C2—C3−1.3 (2)C1—C11—C23—C24−9.78 (18)
C11—C1—C2—C3177.52 (13)C12—C11—C23—C24119.09 (13)
C1—C2—C3—C82.1 (2)C1—C11—C23—C30108.89 (13)
C1—C2—C3—C4−175.45 (14)C12—C11—C23—C30−122.25 (12)
C8—C3—C4—C5−0.9 (2)C1—C11—C23—C14−136.15 (12)
C2—C3—C4—C5176.61 (14)C12—C11—C23—C14−7.29 (13)
C3—C4—C5—C61.4 (2)N2—C14—C23—C24−150.97 (11)
C4—C5—C6—C7−0.2 (2)C22—C14—C23—C2486.94 (14)
C5—C6—C7—C8−1.5 (2)C15—C14—C23—C24−25.39 (15)
C4—C3—C8—N1177.54 (13)N2—C14—C23—C3097.99 (12)
C2—C3—C8—N1−0.1 (2)C22—C14—C23—C30−24.10 (15)
C4—C3—C8—C7−0.8 (2)C15—C14—C23—C30−136.42 (12)
C2—C3—C8—C7−178.43 (13)N2—C14—C23—C11−19.61 (12)
C6—C7—C8—N1−176.40 (14)C22—C14—C23—C11−141.71 (11)
C6—C7—C8—C32.0 (2)C15—C14—C23—C11105.97 (12)
C2—C1—C9—N1−1.6 (2)C30—C23—C24—C25−168.81 (14)
C11—C1—C9—N1179.44 (14)C11—C23—C24—C25−45.3 (2)
C2—C1—C9—O1178.08 (12)C14—C23—C24—C2576.33 (18)
C11—C1—C9—O1−0.85 (19)C30—C23—C24—C2911.01 (14)
C2—C1—C11—C12−3.5 (2)C11—C23—C24—C29134.53 (13)
C9—C1—C11—C12175.32 (12)C14—C23—C24—C29−103.85 (13)
C2—C1—C11—C23119.73 (15)C29—C24—C25—C260.3 (2)
C9—C1—C11—C23−61.45 (17)C23—C24—C25—C26−179.91 (14)
C1—C11—C12—N2159.38 (11)C24—C25—C26—C270.7 (2)
C23—C11—C12—N231.44 (13)C25—C26—C27—C28−0.7 (2)
N2—C14—C15—O335.42 (19)C26—C27—C28—C29−0.2 (2)
C22—C14—C15—O3158.85 (14)C27—C28—C29—C241.2 (2)
C23—C14—C15—O3−81.49 (17)C27—C28—C29—N3−175.11 (14)
N2—C14—C15—C16−141.36 (12)C25—C24—C29—C28−1.3 (2)
C22—C14—C15—C16−17.93 (14)C23—C24—C29—C28178.90 (13)
C23—C14—C15—C16101.74 (12)C25—C24—C29—N3175.66 (12)
O3—C15—C16—C1713.5 (3)C23—C24—C29—N3−4.18 (15)
C14—C15—C16—C17−169.79 (15)C24—C23—C30—O2167.42 (13)
O3—C15—C16—C21−164.90 (14)C11—C23—C30—O237.77 (18)
C14—C15—C16—C2111.84 (15)C14—C23—C30—O2−74.05 (16)
C21—C16—C17—C181.0 (2)C24—C23—C30—N3−14.36 (13)
C15—C16—C17—C18−177.20 (15)C11—C23—C30—N3−144.01 (11)
C16—C17—C18—C19−0.2 (3)C14—C23—C30—N3104.18 (12)
C17—C18—C19—C20−0.8 (3)O1—C9—N1—C8−176.13 (12)
C18—C19—C20—C210.9 (2)C1—C9—N1—C83.6 (2)
C17—C16—C21—C20−0.9 (2)C3—C8—N1—C9−2.6 (2)
C15—C16—C21—C20177.64 (13)C7—C8—N1—C9175.76 (14)
C17—C16—C21—C22−178.35 (14)C22—C14—N2—C13−68.82 (15)
C15—C16—C21—C220.15 (16)C15—C14—N2—C1348.69 (16)
C19—C20—C21—C16−0.1 (2)C23—C14—N2—C13168.92 (11)
C19—C20—C21—C22176.86 (15)C22—C14—N2—C12163.46 (11)
C16—C21—C22—O4164.54 (15)C15—C14—N2—C12−79.03 (14)
C20—C21—C22—O4−12.7 (3)C23—C14—N2—C1241.21 (13)
C16—C21—C22—C14−12.15 (16)C11—C12—N2—C14−46.38 (13)
C20—C21—C22—C14170.62 (15)C11—C12—N2—C13−175.31 (11)
N2—C14—C22—O4−32.2 (2)O2—C30—N3—C29−168.83 (13)
C15—C14—C22—O4−158.68 (14)C23—C30—N3—C2912.97 (15)
C23—C14—C22—O484.30 (18)C28—C29—N3—C30170.86 (14)
N2—C14—C22—C21144.58 (12)C24—C29—N3—C30−5.81 (16)
C15—C14—C22—C2118.10 (14)N1—C9—O1—C10−6.3 (2)
C23—C14—C22—C21−98.91 (13)C1—C9—O1—C10173.97 (13)
D—H···AD—HH···AD···AD—H···A
N3—H3···N2i0.862.192.971 (2)151
C4—H4···O3ii0.932.563.350 (2)143
C6—H6···O4iii0.932.423.307 (2)159
C12—H12A···O2iv0.972.533.325 (2)139
C28—H28···O4i0.932.563.354 (1)144
C18—H18···Cg1v0.932.893.778 (6)160
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C3–C8 ring.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N3—H3⋯N2i 0.862.192.971 (2)151
C4—H4⋯O3ii 0.932.563.350 (2)143
C6—H6⋯O4iii 0.932.423.307 (2)159
C12—H12A⋯O2iv 0.972.533.325 (2)139
C28—H28⋯O4i 0.932.563.354 (1)144
C18—H18⋯Cg1v 0.932.893.778 (6)160

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

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Authors:  George M Sheldrick
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Journal:  Bioorg Med Chem       Date:  2004-10-01       Impact factor: 3.641

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Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-06-20

4.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20

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