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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2935.
Published online 2010 October 23. doi:  10.1107/S1600536810041917
PMCID: PMC3009029

3′-Hy­droxy­methyl-1′-methyl-3′-nitro-4′-(o-tol­yl)spiro­[indoline-3,2′-pyrrolidin]-2-one

Abstract

The title compound, C20H21N3O4, crystallizes with two mol­ecules in the asymmetric unit. In both mol­ecules, the pyrrolidine ring adopts an envelope conformation. The crystal structure is stabilized by inter­molecular C—H(...)O, N—H(...)O and O—H(...)O hydrogen bonds.

Related literature

For ring puckering parameters, see: Cremer & Pople (1975 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2935-scheme1.jpg

Experimental

Crystal data

  • C20H21N3O4
  • M r = 367.40
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2935-efi1.jpg
  • a = 10.8757 (18) Å
  • b = 13.625 (2) Å
  • c = 13.656 (2) Å
  • α = 66.116 (8)°
  • β = 83.715 (8)°
  • γ = 78.991 (9)°
  • V = 1814.9 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 293 K
  • 0.30 × 0.26 × 0.20 mm

Data collection

  • Bruker APEXII CCD area detector diffractometer
  • 32702 measured reflections
  • 9209 independent reflections
  • 5980 reflections with I > 2Σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.131
  • S = 1.03
  • 9209 reflections
  • 493 parameters
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810041917/bt5370sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041917/bt5370Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

RG and KS thank the Technology Business Incubator (TBI), CAS in Crystallography and Biophysics, University of Madras, Chennai, and the Department of Science and Technology (DST) for the data collection.

supplementary crystallographic information

Comment

Substituted pyrrolidine compounds have gained much importance since they are the basic structural elements of many alkaloids and pharmacologically active compounds while molecules with the indole moiety posses anti-inflammatory and antibacterial properties In the title structure the asymmetric unit contains a pair of molecules with almost identical geometry. In the two molecules the bond lengths and angles agree with each other. In the benzene ring of the indole system the endocyclic angles at C17 and C20 are contracted to 118.78 (14)° and 117.64 (16)° respectively while those at C18, C19 and C15 are expanded to 120.92 (16)°, 121.19 (19)° and 121.56 (16)°, respectively. The sum of bond angles around N2 [331.33°] and around N3 atom [359.90°] indicate sp3 and sp2 hybridizations respectively. Dihedral angle formed between pyrrolidine ring and benzene ring is 71.98 (10)° and the dihedral angle between oxindole moiety and benzene ring is 45.04 (8)°. In addition to van der Waals interactions there are intermolecular C—H···O , N—H···O and O—H···O hydrogen bonds.

Experimental

A mixture of (E) -2 nitro -3 o- tolyprop -2 en -1-ol(2 mmol,0.386 g) isatin (2 mmol,0.29 g) and sarcosine (2 mmol,0.18 g) in acetonitrile(8 mL) was refluxed for 5 h.After the completion of the reaction as indicated by TLC, the reaction mixture was concentrated and the resulting crude mass was diluted with water (10 ml) and extracted with ethyl acetate(3 X 10 ml).The combined organic layers were washed with brine and dried over anhydrous Na2 sO4. The organic layer was concentrated and the residue purified by column chromatography on Silica Gel (Acme 100–200 mesh),using ethyl acetate, hexanes (2:8) to afford final product as a olourless solid in 75% (0.55 g) yield.

Refinement

H atoms were placed in idealized positions and allowed to ride on their parent atoms, with C—H bond lengths fixed to 0.93Å (aromatic H), 0.96Å (methyl H), 0.97Å (methylene H), 0.98Å (methine H), 0.82Å (OH), 0.86Å (NH), and Uiso(H)=1.2 - 1.5 Ueq(C,N).

Figures

Fig. 1.
The molecular structure of title compound showing 50% probability displacement ellipsoids.
Fig. 2.
Packing diagram of the molecules viewed along the A axis.

Crystal data

C20H21N3O4Z = 4
Mr = 367.40F(000) = 776
Triclinic, P1Dx = 1.345 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.8757 (18) ÅCell parameters from 9209 reflections
b = 13.625 (2) Åθ = 1.6–28.7°
c = 13.656 (2) ŵ = 0.10 mm1
α = 66.116 (8)°T = 293 K
β = 83.715 (8)°Black, black
γ = 78.991 (9)°0.30 × 0.26 × 0.20 mm
V = 1814.9 (5) Å3

Data collection

Bruker APEXII CCD area detector diffractometer5980 reflections with I > 2Σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
graphiteθmax = 28.7°, θmin = 1.6°
ω and [var phi] scansh = −14→14
32702 measured reflectionsk = −18→18
9209 independent reflectionsl = −18→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0564P)2 + 0.3018P] where P = (Fo2 + 2Fc2)/3
9209 reflections(Δ/σ)max < 0.001
493 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = −0.18 e Å3

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 (Å2)

xyzUiso*/Ueq
C10.9263 (2)0.78067 (16)0.12135 (15)0.0643 (5)
H10.86160.77280.08720.077*
C21.0088 (2)0.84968 (17)0.06218 (15)0.0736 (6)
H21.00020.8872−0.01130.088*
C31.1032 (2)0.86301 (17)0.11143 (15)0.0720 (6)
H31.15880.91000.07150.086*
C41.11632 (19)0.80676 (14)0.22033 (13)0.0546 (4)
H41.18080.81650.25330.066*
C51.03477 (15)0.73560 (12)0.28191 (11)0.0410 (3)
C60.93751 (16)0.72207 (13)0.23161 (13)0.0468 (4)
C70.84219 (18)0.65016 (16)0.29240 (15)0.0606 (5)
H7A0.88440.57800.33230.091*
H7B0.78770.64780.24290.091*
H7C0.79370.67880.34080.091*
C81.04939 (14)0.67486 (11)0.40162 (11)0.0366 (3)
H81.01780.60630.42200.044*
C91.18353 (15)0.64548 (13)0.43989 (12)0.0444 (4)
H9A1.22550.57840.43410.053*
H9B1.23170.70310.39880.053*
C101.28322 (17)0.61668 (16)0.60404 (15)0.0585 (5)
H10A1.32310.67990.56900.088*
H10B1.33810.55420.59980.088*
H10C1.26500.60540.67790.088*
C111.07282 (14)0.72425 (10)0.55415 (11)0.0338 (3)
C120.97488 (13)0.73354 (10)0.47288 (10)0.0327 (3)
C130.90941 (15)0.84833 (11)0.40830 (11)0.0394 (3)
H13A0.96470.88350.34870.047*
H13B0.83490.84330.37870.047*
C141.12455 (15)0.83425 (12)0.51371 (12)0.0410 (3)
C151.05989 (15)0.79408 (12)0.68790 (12)0.0417 (3)
C161.03173 (14)0.70849 (11)0.66827 (11)0.0356 (3)
C170.98993 (15)0.62187 (12)0.75116 (12)0.0421 (3)
H170.97360.56300.73950.051*
C180.97263 (17)0.62392 (14)0.85264 (12)0.0510 (4)
H180.94420.56590.90930.061*
C190.99680 (18)0.71000 (16)0.87043 (13)0.0586 (5)
H190.98350.71000.93890.070*
C201.04078 (18)0.79743 (16)0.78823 (14)0.0566 (5)
H201.05680.85620.80030.068*
N10.87235 (12)0.66862 (9)0.53968 (9)0.0371 (3)
N21.16682 (12)0.63274 (9)0.55149 (10)0.0398 (3)
N31.11411 (14)0.86594 (11)0.59629 (10)0.0490 (3)
H3A1.13820.92390.59280.059*
O10.89335 (12)0.57011 (8)0.57472 (9)0.0532 (3)
O20.77393 (11)0.72006 (9)0.55803 (10)0.0551 (3)
O30.87436 (11)0.91441 (8)0.46729 (8)0.0444 (3)
H3B0.81820.89120.51120.067*
O41.16951 (12)0.88053 (9)0.42497 (9)0.0547 (3)
C210.2916 (2)0.53247 (16)0.0557 (2)0.0802 (7)
H210.23970.58770.00490.096*
C220.3238 (3)0.54936 (18)0.1412 (2)0.0935 (8)
H220.29220.61430.14900.112*
C230.4028 (3)0.46985 (19)0.2153 (2)0.0886 (7)
H230.42630.48090.27310.106*
C240.4473 (2)0.37329 (16)0.20326 (17)0.0690 (5)
H240.50220.32020.25280.083*
C250.41187 (17)0.35323 (13)0.11889 (13)0.0531 (4)
C260.33357 (18)0.43623 (15)0.04218 (15)0.0604 (5)
C270.2939 (2)0.42400 (18)−0.05373 (17)0.0790 (6)
H27A0.23900.4886−0.09510.118*
H27B0.25090.3626−0.03030.118*
H27C0.36660.4130−0.09710.118*
C280.45817 (16)0.24525 (13)0.10977 (12)0.0486 (4)
H280.44040.25560.03710.058*
C290.59902 (17)0.20421 (14)0.12277 (14)0.0554 (4)
H29A0.64580.23890.05670.066*
H29B0.62940.21750.17980.066*
C300.73427 (17)0.02658 (16)0.17691 (16)0.0635 (5)
H30A0.75920.03090.24020.095*
H30B0.79240.05600.11860.095*
H30C0.7337−0.04810.19000.095*
C310.51057 (15)0.05040 (12)0.23065 (11)0.0413 (3)
C320.39654 (15)0.14565 (12)0.18795 (12)0.0418 (3)
C330.30840 (17)0.16622 (13)0.27485 (13)0.0484 (4)
H33A0.34050.21610.29620.058*
H33B0.22710.20170.24460.058*
C340.54213 (17)0.03808 (14)0.34425 (12)0.0503 (4)
C350.52243 (17)−0.13051 (14)0.35819 (15)0.0586 (5)
C360.49706 (16)−0.06504 (13)0.25191 (14)0.0501 (4)
C370.47687 (19)−0.11189 (17)0.18355 (19)0.0674 (5)
H370.4634−0.06960.11140.081*
C380.4771 (2)−0.2231 (2)0.2245 (3)0.0873 (8)
H380.4622−0.25530.17940.105*
C390.4988 (2)−0.28621 (19)0.3300 (3)0.0939 (9)
H390.4970−0.36050.35580.113*
C400.5232 (2)−0.24172 (17)0.3991 (2)0.0799 (7)
H400.5396−0.28490.47060.096*
N40.31886 (15)0.10989 (13)0.12409 (13)0.0566 (4)
N50.55111 (16)−0.06837 (12)0.40917 (11)0.0628 (4)
H50.5723−0.09470.47490.075*
N60.60896 (12)0.08871 (11)0.14952 (10)0.0466 (3)
O50.23358 (14)0.06078 (13)0.17280 (14)0.0789 (4)
O60.34711 (16)0.12759 (14)0.03015 (11)0.0842 (5)
O70.29185 (12)0.07180 (9)0.36754 (9)0.0552 (3)
H70.25180.03470.35280.083*
O80.55874 (14)0.11090 (11)0.36834 (9)0.0677 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0829 (15)0.0693 (12)0.0493 (10)−0.0064 (11)−0.0125 (10)−0.0323 (9)
C20.1127 (19)0.0718 (13)0.0344 (9)−0.0196 (13)−0.0010 (11)−0.0173 (9)
C30.1015 (17)0.0757 (13)0.0402 (10)−0.0334 (12)0.0126 (10)−0.0194 (9)
C40.0684 (12)0.0590 (10)0.0405 (9)−0.0226 (9)0.0074 (8)−0.0205 (8)
C50.0517 (10)0.0396 (8)0.0358 (7)−0.0073 (7)0.0033 (7)−0.0203 (6)
C60.0548 (10)0.0475 (9)0.0445 (9)−0.0053 (7)−0.0011 (8)−0.0261 (7)
C70.0559 (12)0.0696 (12)0.0645 (11)−0.0155 (9)−0.0081 (9)−0.0310 (10)
C80.0442 (9)0.0317 (7)0.0368 (7)−0.0077 (6)0.0025 (6)−0.0167 (6)
C90.0444 (9)0.0455 (8)0.0456 (8)−0.0049 (7)0.0041 (7)−0.0227 (7)
C100.0453 (10)0.0712 (12)0.0550 (10)−0.0050 (9)−0.0069 (8)−0.0215 (9)
C110.0404 (8)0.0293 (7)0.0319 (7)−0.0098 (6)0.0008 (6)−0.0110 (5)
C120.0395 (8)0.0281 (6)0.0312 (7)−0.0087 (5)0.0026 (6)−0.0118 (5)
C130.0519 (9)0.0301 (7)0.0348 (7)−0.0035 (6)−0.0003 (7)−0.0128 (6)
C140.0481 (9)0.0360 (7)0.0407 (8)−0.0160 (7)−0.0003 (7)−0.0134 (6)
C150.0458 (9)0.0435 (8)0.0396 (8)−0.0128 (7)−0.0010 (7)−0.0179 (7)
C160.0392 (8)0.0348 (7)0.0328 (7)−0.0072 (6)−0.0019 (6)−0.0126 (6)
C170.0459 (9)0.0392 (8)0.0369 (8)−0.0083 (7)−0.0016 (7)−0.0099 (6)
C180.0516 (10)0.0591 (10)0.0323 (8)−0.0101 (8)0.0005 (7)−0.0080 (7)
C190.0610 (12)0.0828 (13)0.0364 (9)−0.0137 (10)0.0013 (8)−0.0277 (9)
C200.0658 (12)0.0698 (11)0.0518 (10)−0.0194 (9)−0.0012 (9)−0.0383 (9)
N10.0420 (7)0.0350 (6)0.0373 (6)−0.0106 (5)0.0003 (5)−0.0159 (5)
N20.0396 (7)0.0377 (6)0.0397 (7)−0.0034 (5)−0.0016 (5)−0.0140 (5)
N30.0667 (10)0.0435 (7)0.0478 (8)−0.0263 (7)0.0024 (7)−0.0227 (6)
O10.0643 (8)0.0329 (6)0.0619 (7)−0.0176 (5)0.0112 (6)−0.0172 (5)
O20.0440 (7)0.0520 (7)0.0673 (8)−0.0083 (5)0.0129 (6)−0.0249 (6)
O30.0569 (7)0.0308 (5)0.0453 (6)−0.0079 (5)0.0104 (5)−0.0175 (5)
O40.0711 (9)0.0487 (6)0.0452 (6)−0.0303 (6)0.0112 (6)−0.0137 (5)
C210.0712 (15)0.0457 (11)0.1031 (18)−0.0113 (10)−0.0016 (13)−0.0078 (11)
C220.099 (2)0.0495 (12)0.128 (2)−0.0200 (12)0.0152 (17)−0.0327 (14)
C230.117 (2)0.0635 (14)0.0929 (17)−0.0343 (14)0.0075 (16)−0.0333 (13)
C240.0852 (15)0.0542 (11)0.0640 (12)−0.0193 (10)−0.0023 (11)−0.0161 (9)
C250.0561 (11)0.0463 (9)0.0447 (9)−0.0151 (8)0.0064 (8)−0.0046 (7)
C260.0514 (11)0.0495 (10)0.0607 (11)−0.0142 (8)0.0055 (9)−0.0011 (8)
C270.0695 (14)0.0789 (14)0.0615 (12)0.0009 (11)−0.0153 (11)−0.0025 (11)
C280.0518 (10)0.0515 (9)0.0320 (8)−0.0074 (7)−0.0005 (7)−0.0064 (7)
C290.0496 (11)0.0566 (10)0.0442 (9)−0.0135 (8)0.0062 (8)−0.0036 (8)
C300.0425 (10)0.0709 (12)0.0600 (11)−0.0038 (9)0.0063 (9)−0.0128 (9)
C310.0396 (9)0.0482 (8)0.0321 (7)−0.0079 (7)0.0036 (6)−0.0126 (6)
C320.0416 (9)0.0473 (8)0.0363 (8)−0.0065 (7)−0.0003 (7)−0.0168 (7)
C330.0497 (10)0.0459 (9)0.0478 (9)−0.0067 (7)0.0086 (8)−0.0195 (7)
C340.0542 (11)0.0562 (10)0.0318 (8)−0.0052 (8)0.0016 (7)−0.0110 (7)
C350.0490 (11)0.0504 (10)0.0614 (11)−0.0055 (8)0.0202 (9)−0.0134 (9)
C360.0391 (9)0.0504 (9)0.0562 (10)−0.0062 (7)0.0120 (8)−0.0201 (8)
C370.0537 (12)0.0693 (12)0.0887 (15)−0.0069 (9)0.0082 (10)−0.0448 (11)
C380.0610 (14)0.0717 (15)0.149 (3)−0.0112 (11)0.0154 (15)−0.0679 (17)
C390.0608 (15)0.0543 (13)0.159 (3)−0.0139 (11)0.0330 (17)−0.0414 (17)
C400.0603 (13)0.0513 (11)0.0947 (16)−0.0041 (9)0.0278 (12)−0.0044 (11)
N40.0489 (9)0.0652 (9)0.0618 (10)−0.0004 (7)−0.0095 (8)−0.0332 (8)
N50.0741 (11)0.0574 (9)0.0347 (7)0.0013 (8)0.0026 (7)−0.0017 (7)
N60.0386 (8)0.0545 (8)0.0351 (7)−0.0059 (6)0.0063 (6)−0.0086 (6)
O50.0528 (9)0.0960 (11)0.1116 (12)−0.0257 (8)0.0061 (8)−0.0613 (10)
O60.0956 (12)0.1114 (12)0.0575 (9)−0.0119 (9)−0.0166 (8)−0.0440 (8)
O70.0605 (8)0.0497 (7)0.0561 (7)−0.0195 (6)0.0224 (6)−0.0230 (6)
O80.0923 (11)0.0693 (8)0.0421 (7)−0.0152 (7)−0.0121 (7)−0.0194 (6)

Geometric parameters (Å, °)

C1—C21.375 (3)C21—C221.371 (4)
C1—C61.396 (2)C21—C261.382 (3)
C1—H10.9300C21—H210.9300
C2—C31.364 (3)C22—C231.373 (4)
C2—H20.9300C22—H220.9300
C3—C41.379 (2)C23—C241.381 (3)
C3—H30.9300C23—H230.9300
C4—C51.392 (2)C24—C251.394 (3)
C4—H40.9300C24—H240.9300
C5—C61.400 (2)C25—C261.403 (3)
C5—C81.514 (2)C25—C281.512 (2)
C6—C71.505 (3)C26—C271.502 (3)
C7—H7A0.9600C27—H27A0.9600
C7—H7B0.9600C27—H27B0.9600
C7—H7C0.9600C27—H27C0.9600
C8—C91.528 (2)C28—C291.531 (2)
C8—C121.5660 (18)C28—C321.565 (2)
C8—H80.9800C28—H280.9800
C9—N21.4570 (19)C29—N61.449 (2)
C9—H9A0.9700C29—H29A0.9700
C9—H9B0.9700C29—H29B0.9700
C10—N21.460 (2)C30—N61.459 (2)
C10—H10A0.9600C30—H30A0.9600
C10—H10B0.9600C30—H30B0.9600
C10—H10C0.9600C30—H30C0.9600
C11—N21.4638 (18)C31—N61.460 (2)
C11—C161.5125 (19)C31—C361.513 (2)
C11—C141.5657 (19)C31—C341.561 (2)
C11—C121.5735 (19)C31—C321.579 (2)
C12—C131.5251 (19)C32—C331.524 (2)
C12—N11.5358 (18)C32—N41.541 (2)
C13—O31.4121 (16)C33—O71.4175 (19)
C13—H13A0.9700C33—H33A0.9700
C13—H13B0.9700C33—H33B0.9700
C14—O41.2141 (18)C34—O81.213 (2)
C14—N31.3485 (19)C34—N51.350 (2)
C15—C201.381 (2)C35—N51.387 (3)
C15—C161.390 (2)C35—C401.385 (3)
C15—N31.392 (2)C35—C361.387 (3)
C16—C171.375 (2)C36—C371.381 (3)
C17—C181.389 (2)C37—C381.386 (3)
C17—H170.9300C37—H370.9300
C18—C191.366 (3)C38—C391.366 (4)
C18—H180.9300C38—H380.9300
C19—C201.387 (3)C39—C401.381 (4)
C19—H190.9300C39—H390.9300
C20—H200.9300C40—H400.9300
N1—O11.2121 (15)N4—O61.221 (2)
N1—O21.2235 (16)N4—O51.221 (2)
N3—H3A0.8600N5—H50.8600
O3—H3B0.8200O7—H70.8200
C2—C1—C6121.46 (19)C22—C21—C26122.2 (2)
C2—C1—H1119.3C22—C21—H21118.9
C6—C1—H1119.3C26—C21—H21118.9
C3—C2—C1119.93 (18)C23—C22—C21119.6 (2)
C3—C2—H2120.0C23—C22—H22120.2
C1—C2—H2120.0C21—C22—H22120.2
C2—C3—C4120.0 (2)C22—C23—C24119.3 (2)
C2—C3—H3120.0C22—C23—H23120.3
C4—C3—H3120.0C24—C23—H23120.3
C3—C4—C5121.21 (18)C23—C24—C25121.8 (2)
C3—C4—H4119.4C23—C24—H24119.1
C5—C4—H4119.4C25—C24—H24119.1
C4—C5—C6118.91 (15)C24—C25—C26118.29 (18)
C4—C5—C8120.78 (14)C24—C25—C28120.69 (16)
C6—C5—C8120.31 (14)C26—C25—C28121.01 (17)
C1—C6—C5118.50 (17)C21—C26—C25118.7 (2)
C1—C6—C7118.91 (17)C21—C26—C27119.01 (19)
C5—C6—C7122.55 (15)C25—C26—C27122.33 (18)
C6—C7—H7A109.5C26—C27—H27A109.5
C6—C7—H7B109.5C26—C27—H27B109.5
H7A—C7—H7B109.5H27A—C27—H27B109.5
C6—C7—H7C109.5C26—C27—H27C109.5
H7A—C7—H7C109.5H27A—C27—H27C109.5
H7B—C7—H7C109.5H27B—C27—H27C109.5
C5—C8—C9115.73 (13)C25—C28—C29115.58 (15)
C5—C8—C12115.67 (11)C25—C28—C32117.28 (13)
C9—C8—C12104.24 (11)C29—C28—C32103.95 (12)
C5—C8—H8106.9C25—C28—H28106.4
C9—C8—H8106.9C29—C28—H28106.4
C12—C8—H8106.9C32—C28—H28106.4
N2—C9—C8103.39 (12)N6—C29—C28103.19 (14)
N2—C9—H9A111.1N6—C29—H29A111.1
C8—C9—H9A111.1C28—C29—H29A111.1
N2—C9—H9B111.1N6—C29—H29B111.1
C8—C9—H9B111.1C28—C29—H29B111.1
H9A—C9—H9B109.0H29A—C29—H29B109.1
N2—C10—H10A109.5N6—C30—H30A109.5
N2—C10—H10B109.5N6—C30—H30B109.5
H10A—C10—H10B109.5H30A—C30—H30B109.5
N2—C10—H10C109.5N6—C30—H30C109.5
H10A—C10—H10C109.5H30A—C30—H30C109.5
H10B—C10—H10C109.5H30B—C30—H30C109.5
N2—C11—C16110.87 (11)N6—C31—C36111.72 (13)
N2—C11—C14113.72 (12)N6—C31—C34113.15 (13)
C16—C11—C14101.40 (11)C36—C31—C34101.14 (13)
N2—C11—C12102.28 (10)N6—C31—C32102.16 (12)
C16—C11—C12120.25 (12)C36—C31—C32120.11 (14)
C14—C11—C12108.79 (11)C34—C31—C32108.97 (12)
C13—C12—N1106.79 (12)C33—C32—N4106.55 (13)
C13—C12—C8113.48 (11)C33—C32—C28115.10 (13)
N1—C12—C8109.38 (10)N4—C32—C28109.66 (12)
C13—C12—C11115.71 (11)C33—C32—C31114.93 (12)
N1—C12—C11106.58 (10)N4—C32—C31105.72 (12)
C8—C12—C11104.63 (11)C28—C32—C31104.48 (13)
O3—C13—C12114.57 (12)O7—C33—C32114.88 (13)
O3—C13—H13A108.6O7—C33—H33A108.5
C12—C13—H13A108.6C32—C33—H33A108.5
O3—C13—H13B108.6O7—C33—H33B108.5
C12—C13—H13B108.6C32—C33—H33B108.5
H13A—C13—H13B107.6H33A—C33—H33B107.5
O4—C14—N3126.40 (13)O8—C34—N5126.64 (16)
O4—C14—C11125.96 (13)O8—C34—C31125.86 (15)
N3—C14—C11107.60 (12)N5—C34—C31107.47 (15)
C20—C15—C16121.56 (15)N5—C35—C40128.5 (2)
C20—C15—N3128.19 (14)N5—C35—C36109.73 (15)
C16—C15—N3110.14 (12)C40—C35—C36121.7 (2)
C17—C16—C15119.84 (13)C37—C36—C35119.50 (17)
C17—C16—C11130.98 (13)C37—C36—C31131.20 (17)
C15—C16—C11108.58 (12)C35—C36—C31108.97 (15)
C16—C17—C18118.78 (15)C36—C37—C38118.8 (2)
C16—C17—H17120.6C36—C37—H37120.6
C18—C17—H17120.6C38—C37—H37120.6
C19—C18—C17120.92 (16)C39—C38—C37121.0 (2)
C19—C18—H18119.5C39—C38—H38119.5
C17—C18—H18119.5C37—C38—H38119.5
C18—C19—C20121.19 (15)C38—C39—C40121.2 (2)
C18—C19—H19119.4C38—C39—H39119.4
C20—C19—H19119.4C40—C39—H39119.4
C15—C20—C19117.64 (15)C39—C40—C35117.7 (2)
C15—C20—H20121.2C39—C40—H40121.2
C19—C20—H20121.2C35—C40—H40121.2
O1—N1—O2123.13 (13)O6—N4—O5123.20 (17)
O1—N1—C12119.39 (12)O6—N4—C32119.69 (16)
O2—N1—C12117.43 (11)O5—N4—C32117.05 (15)
C9—N2—C10114.40 (13)C34—N5—C35112.54 (15)
C9—N2—C11106.64 (11)C34—N5—H5123.7
C10—N2—C11115.29 (12)C35—N5—H5123.7
C14—N3—C15112.25 (12)C29—N6—C31106.72 (12)
C14—N3—H3A123.9C29—N6—C30114.73 (15)
C15—N3—H3A123.9C31—N6—C30115.07 (12)
C13—O3—H3B109.5C33—O7—H7109.5
C6—C1—C2—C3−0.8 (3)C26—C21—C22—C231.7 (4)
C1—C2—C3—C40.4 (3)C21—C22—C23—C24−1.0 (4)
C2—C3—C4—C50.2 (3)C22—C23—C24—C25−1.4 (4)
C3—C4—C5—C6−0.4 (3)C23—C24—C25—C263.0 (3)
C3—C4—C5—C8−179.53 (16)C23—C24—C25—C28−177.8 (2)
C2—C1—C6—C50.6 (3)C22—C21—C26—C250.0 (3)
C2—C1—C6—C7178.36 (18)C22—C21—C26—C27179.9 (2)
C4—C5—C6—C10.0 (2)C24—C25—C26—C21−2.2 (3)
C8—C5—C6—C1179.15 (14)C28—C25—C26—C21178.53 (17)
C4—C5—C6—C7−177.67 (16)C24—C25—C26—C27177.82 (19)
C8—C5—C6—C71.5 (2)C28—C25—C26—C27−1.4 (3)
C4—C5—C8—C9−31.83 (19)C24—C25—C28—C29−47.9 (2)
C6—C5—C8—C9149.07 (14)C26—C25—C28—C29131.35 (17)
C4—C5—C8—C1290.49 (18)C24—C25—C28—C3275.3 (2)
C6—C5—C8—C12−88.62 (16)C26—C25—C28—C32−105.46 (18)
C5—C8—C9—N2156.71 (11)C25—C28—C29—N6159.94 (13)
C12—C8—C9—N228.50 (14)C32—C28—C29—N629.97 (16)
C5—C8—C12—C13−5.69 (18)C25—C28—C32—C33−7.8 (2)
C9—C8—C12—C13122.55 (13)C29—C28—C32—C33121.12 (15)
C5—C8—C12—N1113.43 (13)C25—C28—C32—N4112.27 (16)
C9—C8—C12—N1−118.33 (12)C29—C28—C32—N4−118.79 (14)
C5—C8—C12—C11−132.72 (13)C25—C28—C32—C31−134.81 (14)
C9—C8—C12—C11−4.48 (13)C29—C28—C32—C31−5.87 (16)
N2—C11—C12—C13−146.49 (12)N6—C31—C32—C33−147.02 (13)
C16—C11—C12—C1390.22 (15)C36—C31—C32—C3388.74 (17)
C14—C11—C12—C13−25.90 (16)C34—C31—C32—C33−27.07 (18)
N2—C11—C12—N194.96 (11)N6—C31—C32—N495.78 (14)
C16—C11—C12—N1−28.33 (15)C36—C31—C32—N4−28.45 (18)
C14—C11—C12—N1−144.44 (11)C34—C31—C32—N4−144.27 (13)
N2—C11—C12—C8−20.86 (13)N6—C31—C32—C28−19.93 (14)
C16—C11—C12—C8−144.14 (12)C36—C31—C32—C28−144.16 (14)
C14—C11—C12—C899.74 (12)C34—C31—C32—C28100.03 (14)
N1—C12—C13—O377.63 (15)N4—C32—C33—O781.97 (17)
C8—C12—C13—O3−161.78 (12)C28—C32—C33—O7−156.24 (14)
C11—C12—C13—O3−40.80 (18)C31—C32—C33—O7−34.8 (2)
N2—C11—C14—O460.5 (2)N6—C31—C34—O862.1 (2)
C16—C11—C14—O4179.52 (16)C36—C31—C34—O8−178.23 (18)
C12—C11—C14—O4−52.8 (2)C32—C31—C34—O8−50.8 (2)
N2—C11—C14—N3−117.40 (14)N6—C31—C34—N5−116.05 (16)
C16—C11—C14—N31.64 (16)C36—C31—C34—N53.58 (17)
C12—C11—C14—N3129.34 (13)C32—C31—C34—N5131.05 (15)
C20—C15—C16—C17−3.4 (2)N5—C35—C36—C37174.38 (16)
N3—C15—C16—C17172.98 (14)C40—C35—C36—C37−2.6 (3)
C20—C15—C16—C11−175.46 (15)N5—C35—C36—C310.2 (2)
N3—C15—C16—C110.97 (18)C40—C35—C36—C31−176.80 (17)
N2—C11—C16—C17−51.3 (2)N6—C31—C36—C37−54.8 (2)
C14—C11—C16—C17−172.36 (16)C34—C31—C36—C37−175.49 (18)
C12—C11—C16—C1767.8 (2)C32—C31—C36—C3764.7 (2)
N2—C11—C16—C15119.53 (13)N6—C31—C36—C35118.41 (15)
C14—C11—C16—C15−1.54 (15)C34—C31—C36—C35−2.24 (17)
C12—C11—C16—C15−121.41 (14)C32—C31—C36—C35−122.05 (15)
C15—C16—C17—C182.2 (2)C35—C36—C37—C382.8 (3)
C11—C16—C17—C18172.19 (15)C31—C36—C37—C38175.49 (18)
C16—C17—C18—C19−0.2 (3)C36—C37—C38—C39−1.0 (3)
C17—C18—C19—C20−0.8 (3)C37—C38—C39—C40−1.1 (4)
C16—C15—C20—C192.4 (3)C38—C39—C40—C351.3 (3)
N3—C15—C20—C19−173.28 (17)N5—C35—C40—C39−175.85 (19)
C18—C19—C20—C15−0.3 (3)C36—C35—C40—C390.5 (3)
C13—C12—N1—O1159.88 (12)C33—C32—N4—O6152.14 (16)
C8—C12—N1—O136.70 (16)C28—C32—N4—O627.0 (2)
C11—C12—N1—O1−75.88 (14)C31—C32—N4—O6−85.15 (18)
C13—C12—N1—O2−22.68 (15)C33—C32—N4—O5−30.58 (19)
C8—C12—N1—O2−145.86 (12)C28—C32—N4—O5−155.76 (15)
C11—C12—N1—O2101.55 (14)C31—C32—N4—O592.13 (17)
C8—C9—N2—C10−173.13 (13)O8—C34—N5—C35178.02 (18)
C8—C9—N2—C11−44.43 (14)C31—C34—N5—C35−3.8 (2)
C16—C11—N2—C9170.06 (12)C40—C35—N5—C34179.13 (19)
C14—C11—N2—C9−76.45 (14)C36—C35—N5—C342.4 (2)
C12—C11—N2—C940.67 (14)C28—C29—N6—C31−45.54 (16)
C16—C11—N2—C10−61.76 (16)C28—C29—N6—C30−174.26 (13)
C14—C11—N2—C1051.73 (17)C36—C31—N6—C29170.46 (14)
C12—C11—N2—C10168.84 (13)C34—C31—N6—C29−76.18 (16)
O4—C14—N3—C15−179.06 (16)C32—C31—N6—C2940.80 (15)
C11—C14—N3—C15−1.20 (18)C36—C31—N6—C30−61.02 (19)
C20—C15—N3—C14176.30 (18)C34—C31—N6—C3052.34 (19)
C16—C15—N3—C140.18 (19)C32—C31—N6—C30169.33 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3A···O3i0.862.002.782 (2)151
O3—H3B···O7ii0.822.112.7769 (17)139
N5—H5···O8iii0.862.393.0064 (19)129
O7—H7···O4iv0.822.242.9356 (19)142
C8—H8···O1v0.982.403.164 (2)135
C33—H33A···O2ii0.972.593.209 (2)122

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5370).

References

  • Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc.97, 1354–1358.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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