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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Jun 18;67(Pt 7):o1733. doi: 10.1107/S1600536811020320

2-[(E)-2-(Benzyl­idene­amino)­eth­yl]-3′,6′-bis­(diethyl­amino)­spiro­[isoindoline-1,9′-xanthen]-3-one

Zhen Wei a,*, Xujun Zheng a, Junjun Bai a, Xiaohong Zhai a, Lili Song a
PMCID: PMC3151774  PMID: 21837122

Abstract

In the title compound, C37H40N4O2, the xanthene and spiro­lactam rings are almost planar, with r.m.s. deviations from the mean planes of 0.223 (2) and 0.057 (2) Å, respectively, and form a dihedral angle of 85.76 (3)°. The dihedral angle between the xanthene mean plane and the benzene ring is 87.16 (5)°. One of the two ethyl groups of one of the diethyl­amino groups is disordered over two sets of sites [0.76 (1):0.24 (1)].

Related literature

For related structures and background to rhodamine dyes, see: Xu et al. (2010a ▶,b ▶); Zhang et al. (2008 ▶); Tian et al. (2008 ▶); Kwon et al. (2005 ▶); Wu et al. (2007 ▶).graphic file with name e-67-o1733-scheme1.jpg

Experimental

Crystal data

  • C37H40N4O2

  • M r = 572.73

  • Triclinic, Inline graphic

  • a = 9.842 (2) Å

  • b = 13.151 (3) Å

  • c = 13.552 (3) Å

  • α = 74.43 (3)°

  • β = 81.92 (3)°

  • γ = 69.12 (3)°

  • V = 1576.7 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.26 × 0.22 × 0.20 mm

Data collection

  • Rigaku Saturn diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T min = 0.981, T max = 0.985

  • 17336 measured reflections

  • 6168 independent reflections

  • 4273 reflections with I > 2σ(I)

  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057

  • wR(F 2) = 0.174

  • S = 1.06

  • 6168 reflections

  • 399 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.24 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811020320/bg2398sup1.cif

e-67-o1733-sup1.cif (30.3KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020320/bg2398Isup2.hkl

e-67-o1733-Isup2.hkl (301.9KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811020320/bg2398Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811020320/bg2398Isup4.cml

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

Acknowledgments

The authors thank the Science Development Committee of Tianjin Agricultural college (research grant No. 2009 N02).

supplementary crystallographic information

Comment

Rhodamine dyes are known to have excellent photophysical properties,and they are one of the most widely used fluorophores for labeling and sensing biomolecules. There are a few single-crystal reports on rhodamine derivatives bearing a lactam moiety (Xu et al., 2010a;2010b Kwon et al., 2005; Wu et al., 2007; Zhang et al., 2008; Tian et al., 2008). Detailed information on their molecular and crystal structures is necessary to understand their photophysical and photochemical properties.

In the title compound, C37H20N4O2, the xanthene and spirolactam-rings are almost planar, with r.m.s. deviations from the mean planes of 0.223 (2)Å and 0.057 (2)Å, respectively, and form a dihedral angle of 85.76 (3)°. The dihedral angle between the xanthene mean plane and the benzene ring is 87.16 (5)°. During refinement, one of the two ethyl groups bonded to N4 appeared disordered. The corresponding occupancies refined to final values of 0.76/0.24 (1).

Experimental

N-(rhodamine-6 G)lactam-ethylenediamine (10m mol) was dissolved in 20 ml of ethanol, followed by addition of benzaldehyde(15m mol). The solution was stirred and refluxed for 4 h when white precipitate appeared,the resulting crude product was obtained by filteration. then the product was disolved in ethanol,Single crystals suitable for X-ray measurements were obtained from ethanol by slow evaporation at room temperature.

Refinement

During refinement, one of the two ethyl groups bonded to N4 appeared disordered. The corresponding occupancies refined to final values of 0.76/0.24 (1), and were kept fixed afterwards. The disordered model was refined using the tools availablein SHELXL97 (Sheldrick, 2008): SADI for restraining distances, EADP to correlate anisotropic thermal parameters for related disordered atoms.

All H atoms were geometrically positioned and treated as riding on their parent atoms, with C—H = 0.93 Å for the aromatic, 0.96 Å for the methyl H atoms and C—H= 0.97 Å for methylene, with Uiso(H)= 1.2 Ueq(C aromatic) or,1.5Ueq(C methyl).

Figures

Fig. 1.

Fig. 1.

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The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Only the major part of the ethyl group attached to N4 has been drawn, for clarity.

Crystal data

C37H40N4O2 Z = 2
Mr = 572.73 F(000) = 612
Triclinic, P1 Dx = 1.206 Mg m−3
Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Å
a = 9.842 (2) Å Cell parameters from 3876 reflections
b = 13.151 (3) Å θ = 1.6–29.0°
c = 13.552 (3) Å µ = 0.08 mm−1
α = 74.43 (3)° T = 293 K
β = 81.92 (3)° Prism, colourless
γ = 69.12 (3)° 0.26 × 0.22 × 0.20 mm
V = 1576.7 (7) Å3
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Data collection

Rigaku Saturn diffractometer 6168 independent reflections
Radiation source: fine-focus sealed tube 4273 reflections with I > 2σ(I)
graphite Rint = 0.033
Detector resolution: 7.31 pixels mm-1 θmax = 26.0°, θmin = 1.6°
ω scans h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008) k = −16→16
Tmin = 0.981, Tmax = 0.985 l = −16→16
17336 measured reflections
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Refinement

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) = 0.174 H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.1016P)2] where P = (Fo2 + 2Fc2)/3
6168 reflections (Δ/σ)max < 0.001
399 parameters Δρmax = 0.29 e Å−3
2 restraints Δρmin = −0.24 e Å−3
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Special details

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 andgoodness 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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq Occ. (<1)
O1 0.33256 (15) 0.41003 (11) 0.03815 (10) 0.0723 (4)
O2 0.36695 (14) 0.00487 (9) 0.43694 (9) 0.0579 (4)
N1 0.31962 (15) 0.25956 (11) 0.16827 (10) 0.0456 (4)
N2 −0.00271 (18) 0.22023 (14) 0.08727 (13) 0.0650 (5)
N3 −0.04621 (17) 0.22186 (14) 0.60535 (13) 0.0665 (5)
N4 0.72011 (19) −0.26509 (12) 0.27732 (12) 0.0652 (5)
C1 0.37105 (19) 0.34525 (14) 0.12145 (13) 0.0506 (4)
C2 0.47929 (18) 0.34194 (13) 0.18879 (13) 0.0487 (4)
C3 0.5722 (2) 0.40412 (15) 0.17296 (16) 0.0628 (5)
H3 0.5670 0.4626 0.1153 0.075*
C4 0.6718 (2) 0.37619 (17) 0.24543 (18) 0.0741 (6)
H4 0.7355 0.4163 0.2363 0.089*
C5 0.6800 (2) 0.28913 (18) 0.33248 (17) 0.0697 (6)
H5 0.7486 0.2719 0.3804 0.084*
C6 0.5866 (2) 0.22835 (16) 0.34780 (13) 0.0569 (5)
H6 0.5904 0.1708 0.4061 0.068*
C7 0.48760 (18) 0.25501 (13) 0.27459 (12) 0.0451 (4)
C8 0.38313 (18) 0.19473 (13) 0.26923 (11) 0.0423 (4)
C9 0.26660 (18) 0.20220 (13) 0.35566 (11) 0.0418 (4)
C10 0.26648 (18) 0.10992 (13) 0.43410 (12) 0.0451 (4)
C11 0.16418 (19) 0.11548 (15) 0.51642 (13) 0.0529 (4)
H11 0.1696 0.0512 0.5679 0.063*
C12 0.05450 (19) 0.21522 (15) 0.52287 (13) 0.0515 (4)
C13 0.0518 (2) 0.30963 (15) 0.44214 (13) 0.0551 (5)
H13 −0.0214 0.3779 0.4424 0.066*
C14 0.1558 (2) 0.30175 (14) 0.36355 (13) 0.0526 (4)
H14 0.1523 0.3661 0.3128 0.063*
C15 0.46646 (17) 0.07377 (13) 0.26878 (11) 0.0423 (4)
C16 0.45792 (18) −0.01265 (13) 0.35126 (12) 0.0446 (4)
C17 0.54006 (19) −0.12331 (14) 0.35451 (13) 0.0512 (4)
H17 0.5299 −0.1786 0.4116 0.061*
C18 0.63747 (19) −0.15355 (14) 0.27427 (13) 0.0500 (4)
C19 0.6473 (2) −0.06638 (15) 0.18986 (13) 0.0585 (5)
H19 0.7104 −0.0829 0.1341 0.070*
C20 0.5653 (2) 0.04237 (15) 0.18886 (13) 0.0553 (5)
H20 0.5758 0.0981 0.1323 0.066*
C21 0.2309 (2) 0.22241 (15) 0.11800 (14) 0.0547 (5)
H21A 0.2580 0.1416 0.1412 0.066*
H21B 0.2539 0.2397 0.0447 0.066*
C22 0.0696 (2) 0.27255 (18) 0.13600 (17) 0.0683 (6)
H22A 0.0443 0.2597 0.2090 0.082*
H22B 0.0383 0.3527 0.1070 0.082*
C23 −0.1125 (2) 0.28245 (17) 0.03626 (15) 0.0606 (5)
H23 −0.1429 0.3593 0.0303 0.073*
C24 −0.1941 (2) 0.23795 (17) −0.01401 (14) 0.0579 (5)
C25 −0.1574 (2) 0.12469 (18) −0.00607 (15) 0.0657 (5)
H25 −0.0794 0.0749 0.0328 0.079*
C26 −0.2341 (3) 0.0835 (2) −0.05482 (16) 0.0771 (6)
H26 −0.2064 0.0070 −0.0501 0.093*
C27 −0.3511 (3) 0.1566 (3) −0.10997 (18) 0.0909 (8)
H27 −0.4045 0.1298 −0.1420 0.109*
C28 −0.3891 (3) 0.2687 (3) −0.1178 (2) 0.1100 (10)
H28 −0.4688 0.3180 −0.1552 0.132*
C29 −0.3110 (3) 0.3104 (2) −0.07097 (19) 0.0887 (7)
H29 −0.3373 0.3872 −0.0780 0.106*
C30 −0.1847 (2) 0.31369 (18) 0.59963 (17) 0.0753 (6)
H30A −0.2600 0.2840 0.6356 0.090*
H30B −0.2090 0.3441 0.5283 0.090*
C31 −0.1861 (3) 0.4074 (2) 0.6441 (2) 0.1015 (8)
H31A −0.2797 0.4651 0.6360 0.152*
H31B −0.1122 0.4378 0.6089 0.152*
H31C −0.1671 0.3791 0.7157 0.152*
C32 −0.0309 (2) 0.12577 (18) 0.69285 (16) 0.0714 (6)
H32A −0.0778 0.1526 0.7533 0.086*
H32B 0.0718 0.0878 0.7052 0.086*
C33 −0.0946 (3) 0.0433 (2) 0.6787 (2) 0.1069 (9)
H33A −0.0736 −0.0204 0.7362 0.160*
H33B −0.0529 0.0194 0.6169 0.160*
H33C −0.1981 0.0778 0.6740 0.160*
C34 0.8377 (3) −0.2893 (2) 0.1969 (2) 0.0724 (8) 0.76
H34A 0.9211 −0.2707 0.2064 0.087* 0.76
H34B 0.8012 −0.2456 0.1294 0.087* 0.76
C35 0.8722 (4) −0.4042 (3) 0.1772 (3) 0.0838 (11) 0.76
H35A 0.8985 −0.4603 0.2399 0.101* 0.76
H35B 0.9519 −0.4170 0.1271 0.101* 0.76
H35C 0.7883 −0.4083 0.1521 0.101* 0.76
C34' 0.7532 (10) −0.3164 (7) 0.1892 (6) 0.0724 (8) 0.24
H34C 0.7230 −0.2566 0.1284 0.087* 0.24
H34D 0.6966 −0.3655 0.1967 0.087* 0.24
C35' 0.9113 (12) −0.3765 (11) 0.1716 (13) 0.0838 (11) 0.24
H35D 0.9623 −0.3235 0.1512 0.101* 0.24
H35E 0.9241 −0.4154 0.1185 0.101* 0.24
H35F 0.9493 −0.4294 0.2338 0.101* 0.24
C36 0.7264 (2) −0.34727 (17) 0.37557 (17) 0.0726 (6)
H36A 0.7233 −0.3119 0.4305 0.087*
H36B 0.8185 −0.4080 0.3772 0.087*
C37 0.6059 (3) −0.3945 (2) 0.3947 (2) 0.0971 (8)
H37A 0.5141 −0.3346 0.3895 0.146*
H37B 0.6116 −0.4430 0.4622 0.146*
H37C 0.6141 −0.4364 0.3447 0.146*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.0802 (10) 0.0692 (9) 0.0529 (8) −0.0277 (8) −0.0096 (7) 0.0163 (7)
O2 0.0672 (8) 0.0433 (7) 0.0453 (7) −0.0118 (6) 0.0151 (6) 0.0002 (5)
N1 0.0533 (8) 0.0474 (8) 0.0364 (7) −0.0224 (7) −0.0069 (6) −0.0005 (6)
N2 0.0600 (10) 0.0694 (10) 0.0723 (11) −0.0221 (8) −0.0126 (9) −0.0222 (8)
N3 0.0568 (10) 0.0709 (10) 0.0628 (10) −0.0188 (8) 0.0170 (8) −0.0147 (8)
N4 0.0704 (11) 0.0488 (9) 0.0634 (10) −0.0074 (8) 0.0043 (8) −0.0128 (7)
C1 0.0550 (10) 0.0468 (9) 0.0428 (9) −0.0187 (8) 0.0009 (8) 0.0016 (7)
C2 0.0527 (10) 0.0439 (9) 0.0494 (10) −0.0218 (8) 0.0033 (8) −0.0060 (7)
C3 0.0675 (12) 0.0515 (11) 0.0722 (13) −0.0327 (10) 0.0081 (10) −0.0077 (9)
C4 0.0715 (14) 0.0742 (14) 0.0979 (17) −0.0446 (12) 0.0074 (12) −0.0334 (13)
C5 0.0708 (13) 0.0849 (15) 0.0701 (13) −0.0379 (12) −0.0069 (10) −0.0277 (11)
C6 0.0650 (12) 0.0646 (11) 0.0467 (10) −0.0285 (10) −0.0059 (9) −0.0114 (8)
C7 0.0509 (9) 0.0464 (9) 0.0412 (9) −0.0225 (8) 0.0015 (7) −0.0091 (7)
C8 0.0510 (9) 0.0420 (9) 0.0347 (8) −0.0213 (7) −0.0037 (7) −0.0017 (6)
C9 0.0488 (9) 0.0409 (9) 0.0370 (8) −0.0185 (8) −0.0020 (7) −0.0066 (7)
C10 0.0479 (9) 0.0425 (9) 0.0430 (9) −0.0172 (8) 0.0007 (7) −0.0059 (7)
C11 0.0591 (11) 0.0514 (10) 0.0461 (10) −0.0249 (9) 0.0088 (8) −0.0054 (8)
C12 0.0502 (10) 0.0578 (11) 0.0507 (10) −0.0227 (9) 0.0050 (8) −0.0171 (8)
C13 0.0559 (11) 0.0497 (10) 0.0541 (10) −0.0115 (8) −0.0003 (8) −0.0126 (8)
C14 0.0643 (11) 0.0449 (10) 0.0444 (9) −0.0184 (9) −0.0008 (8) −0.0044 (7)
C15 0.0466 (9) 0.0437 (9) 0.0367 (8) −0.0194 (7) −0.0008 (7) −0.0042 (7)
C16 0.0475 (9) 0.0474 (10) 0.0396 (8) −0.0205 (8) 0.0034 (7) −0.0077 (7)
C17 0.0565 (10) 0.0426 (10) 0.0482 (10) −0.0155 (8) 0.0019 (8) −0.0041 (7)
C18 0.0472 (9) 0.0503 (10) 0.0510 (10) −0.0134 (8) −0.0032 (8) −0.0131 (8)
C19 0.0634 (12) 0.0615 (12) 0.0445 (10) −0.0178 (10) 0.0106 (8) −0.0137 (8)
C20 0.0623 (11) 0.0529 (11) 0.0434 (9) −0.0189 (9) 0.0073 (8) −0.0051 (8)
C21 0.0599 (11) 0.0590 (11) 0.0493 (10) −0.0219 (9) −0.0108 (8) −0.0125 (8)
C22 0.0575 (12) 0.0759 (13) 0.0827 (14) −0.0222 (10) −0.0096 (10) −0.0340 (11)
C23 0.0518 (11) 0.0662 (12) 0.0636 (12) −0.0170 (10) −0.0020 (9) −0.0192 (10)
C24 0.0488 (10) 0.0715 (13) 0.0538 (11) −0.0186 (9) −0.0001 (8) −0.0188 (9)
C25 0.0618 (12) 0.0814 (15) 0.0604 (12) −0.0309 (11) −0.0017 (9) −0.0183 (10)
C26 0.0852 (16) 0.1079 (17) 0.0617 (13) −0.0579 (14) 0.0115 (12) −0.0309 (12)
C27 0.0702 (15) 0.161 (3) 0.0698 (15) −0.0571 (17) 0.0031 (12) −0.0519 (16)
C28 0.0725 (17) 0.159 (3) 0.098 (2) −0.0152 (18) −0.0340 (15) −0.047 (2)
C29 0.0691 (14) 0.1021 (18) 0.0879 (17) −0.0075 (13) −0.0237 (13) −0.0300 (14)
C30 0.0560 (12) 0.0891 (15) 0.0778 (14) −0.0188 (11) 0.0111 (10) −0.0295 (12)
C31 0.103 (2) 0.0996 (19) 0.0962 (18) −0.0119 (15) −0.0012 (15) −0.0454 (15)
C32 0.0767 (14) 0.0844 (14) 0.0616 (12) −0.0423 (12) 0.0242 (10) −0.0242 (10)
C33 0.115 (2) 0.114 (2) 0.116 (2) −0.0718 (18) 0.0348 (17) −0.0437 (17)
C34 0.0742 (19) 0.0536 (15) 0.0874 (18) −0.0204 (13) 0.0190 (16) −0.0261 (13)
C35 0.098 (3) 0.072 (2) 0.0880 (19) −0.0393 (16) 0.0252 (19) −0.0309 (19)
C34' 0.0742 (19) 0.0536 (15) 0.0874 (18) −0.0204 (13) 0.0190 (16) −0.0261 (13)
C35' 0.098 (3) 0.072 (2) 0.0880 (19) −0.0393 (16) 0.0252 (19) −0.0309 (19)
C36 0.0678 (13) 0.0586 (12) 0.0777 (14) −0.0027 (11) −0.0078 (11) −0.0169 (11)
C37 0.122 (2) 0.0702 (15) 0.0990 (19) −0.0350 (15) −0.0047 (17) −0.0172 (13)
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Geometric parameters (Å, °)

O1—C1 1.2319 (19) C21—H21A 0.9700
O2—C10 1.377 (2) C21—H21B 0.9700
O2—C16 1.3810 (19) C22—H22A 0.9700
N1—C1 1.364 (2) C22—H22B 0.9700
N1—C21 1.455 (2) C23—C24 1.468 (3)
N1—C8 1.491 (2) C23—H23 0.9300
N2—C23 1.261 (2) C24—C29 1.378 (3)
N2—C22 1.463 (2) C24—C25 1.379 (3)
N3—C12 1.385 (2) C25—C26 1.387 (3)
N3—C30 1.459 (3) C25—H25 0.9300
N3—C32 1.461 (3) C26—C27 1.370 (3)
N4—C18 1.393 (2) C26—H26 0.9300
N4—C36 1.466 (3) C27—C28 1.364 (4)
N4—C34 1.482 (3) C27—H27 0.9300
N4—C34' 1.467 (7) C28—C29 1.386 (3)
C1—C2 1.479 (2) C28—H28 0.9300
C2—C7 1.383 (2) C29—H29 0.9300
C2—C3 1.391 (2) C30—C31 1.506 (3)
C3—C4 1.371 (3) C30—H30A 0.9700
C3—H3 0.9300 C30—H30B 0.9700
C4—C5 1.395 (3) C31—H31A 0.9600
C4—H4 0.9300 C31—H31B 0.9600
C5—C6 1.381 (3) C31—H31C 0.9600
C5—H5 0.9300 C32—C33 1.496 (3)
C6—C7 1.378 (2) C32—H32A 0.9700
C6—H6 0.9300 C32—H32B 0.9700
C7—C8 1.524 (2) C33—H33A 0.9600
C8—C15 1.509 (2) C33—H33B 0.9600
C8—C9 1.517 (2) C33—H33C 0.9600
C9—C10 1.382 (2) C34—C35 1.515 (4)
C9—C14 1.393 (2) C34—H34A 0.9700
C10—C11 1.393 (2) C34—H34B 0.9801
C11—C12 1.385 (3) C35—H35A 0.9600
C11—H11 0.9300 C35—H35B 0.9600
C12—C13 1.412 (2) C35—H35C 0.9600
C13—C14 1.367 (2) C34'—C35' 1.492 (9)
C13—H13 0.9300 C34'—H34C 0.9696
C14—H14 0.9300 C34'—H34D 0.9710
C15—C16 1.381 (2) C35'—H35D 0.9600
C15—C20 1.395 (2) C35'—H35E 0.9600
C16—C17 1.382 (2) C35'—H35F 0.9600
C17—C18 1.388 (2) C36—C37 1.488 (3)
C17—H17 0.9300 C36—H36A 0.9700
C18—C19 1.406 (2) C36—H36B 0.9700
C19—C20 1.366 (2) C37—H37A 0.9600
C19—H19 0.9300 C37—H37B 0.9600
C20—H20 0.9300 C37—H37C 0.9600
C21—C22 1.498 (3)
C10—O2—C16 118.54 (12) N2—C22—C21 108.56 (16)
C1—N1—C21 123.41 (14) N2—C22—H22A 110.0
C1—N1—C8 113.61 (13) C21—C22—H22A 110.0
C21—N1—C8 122.21 (13) N2—C22—H22B 110.0
C23—N2—C22 118.20 (18) C21—C22—H22B 110.0
C12—N3—C30 121.57 (16) H22A—C22—H22B 108.4
C12—N3—C32 120.37 (16) N2—C23—C24 122.38 (19)
C30—N3—C32 116.85 (16) N2—C23—H23 118.8
C18—N4—C36 118.08 (16) C24—C23—H23 118.8
C18—N4—C34 118.14 (17) C29—C24—C25 118.5 (2)
C36—N4—C34 119.76 (17) C29—C24—C23 119.7 (2)
C18—N4—C34' 124.8 (4) C25—C24—C23 121.83 (18)
C36—N4—C34' 112.6 (4) C24—C25—C26 121.4 (2)
O1—C1—N1 124.55 (17) C24—C25—H25 119.3
O1—C1—C2 128.61 (16) C26—C25—H25 119.3
N1—C1—C2 106.83 (13) C27—C26—C25 119.3 (2)
C7—C2—C3 120.98 (17) C27—C26—H26 120.3
C7—C2—C1 108.63 (14) C25—C26—H26 120.3
C3—C2—C1 130.17 (16) C28—C27—C26 119.8 (2)
C4—C3—C2 117.64 (17) C28—C27—H27 120.1
C4—C3—H3 121.2 C26—C27—H27 120.1
C2—C3—H3 121.2 C27—C28—C29 121.0 (2)
C3—C4—C5 121.62 (18) C27—C28—H28 119.5
C3—C4—H4 119.2 C29—C28—H28 119.5
C5—C4—H4 119.2 C24—C29—C28 119.9 (3)
C6—C5—C4 120.29 (19) C24—C29—H29 120.0
C6—C5—H5 119.9 C28—C29—H29 120.0
C4—C5—H5 119.9 N3—C30—C31 114.5 (2)
C7—C6—C5 118.37 (17) N3—C30—H30A 108.6
C7—C6—H6 120.8 C31—C30—H30A 108.6
C5—C6—H6 120.8 N3—C30—H30B 108.6
C6—C7—C2 121.08 (16) C31—C30—H30B 108.6
C6—C7—C8 128.26 (14) H30A—C30—H30B 107.6
C2—C7—C8 110.54 (14) C30—C31—H31A 109.5
N1—C8—C15 111.68 (13) C30—C31—H31B 109.5
N1—C8—C9 111.33 (13) H31A—C31—H31B 109.5
C15—C8—C9 110.18 (12) C30—C31—H31C 109.5
N1—C8—C7 100.36 (12) H31A—C31—H31C 109.5
C15—C8—C7 110.20 (13) H31B—C31—H31C 109.5
C9—C8—C7 112.79 (13) N3—C32—C33 113.9 (2)
C10—C9—C14 115.44 (15) N3—C32—H32A 108.8
C10—C9—C8 121.58 (14) C33—C32—H32A 108.8
C14—C9—C8 122.95 (13) N3—C32—H32B 108.8
O2—C10—C9 122.77 (15) C33—C32—H32B 108.8
O2—C10—C11 114.51 (14) H32A—C32—H32B 107.7
C9—C10—C11 122.72 (16) C32—C33—H33A 109.5
C12—C11—C10 121.02 (16) C32—C33—H33B 109.5
C12—C11—H11 119.5 H33A—C33—H33B 109.5
C10—C11—H11 119.5 C32—C33—H33C 109.5
N3—C12—C11 121.37 (16) H33A—C33—H33C 109.5
N3—C12—C13 121.87 (16) H33B—C33—H33C 109.5
C11—C12—C13 116.76 (16) N4—C34—C35 112.9 (2)
C14—C13—C12 120.69 (16) N4—C34—H34A 112.6
C14—C13—H13 119.7 C35—C34—H34A 115.5
C12—C13—H13 119.7 N4—C34—H34B 109.8
C13—C14—C9 123.34 (15) C35—C34—H34B 97.1
C13—C14—H14 118.3 H34A—C34—H34B 107.5
C9—C14—H14 118.3 N4—C34'—C35' 113.8 (9)
C16—C15—C20 115.59 (15) N4—C34'—H34C 107.5
C16—C15—C8 121.89 (14) C35'—C34'—H34C 106.6
C20—C15—C8 122.34 (14) N4—C34'—H34D 109.6
O2—C16—C15 122.60 (15) C35'—C34'—H34D 111.1
O2—C16—C17 114.83 (14) H34B—C34'—H34D 146.2
C15—C16—C17 122.57 (16) H34C—C34'—H34D 107.9
C16—C17—C18 121.29 (15) C34'—C35'—H35D 109.5
C16—C17—H17 119.4 C34'—C35'—H35E 109.5
C18—C17—H17 119.4 H35D—C35'—H35E 109.5
C17—C18—N4 121.37 (16) C34'—C35'—H35F 109.5
C17—C18—C19 116.72 (16) H35D—C35'—H35F 109.5
N4—C18—C19 121.91 (16) H35E—C35'—H35F 109.5
C20—C19—C18 120.76 (16) N4—C36—C37 113.50 (19)
C20—C19—H19 119.6 N4—C36—H36A 108.9
C18—C19—H19 119.6 C37—C36—H36A 108.9
C19—C20—C15 123.05 (16) N4—C36—H36B 108.9
C19—C20—H20 118.5 C37—C36—H36B 108.9
C15—C20—H20 118.5 H36A—C36—H36B 107.7
N1—C21—C22 115.50 (15) C36—C37—H37A 109.5
N1—C21—H21A 108.4 C36—C37—H37B 109.5
C22—C21—H21A 108.4 H37A—C37—H37B 109.5
N1—C21—H21B 108.4 C36—C37—H37C 109.5
C22—C21—H21B 108.4 H37A—C37—H37C 109.5
H21A—C21—H21B 107.5 H37B—C37—H37C 109.5
C21—N1—C1—O1 10.6 (3) N1—C8—C15—C16 −138.91 (15)
C8—N1—C1—O1 −179.33 (17) C9—C8—C15—C16 −14.6 (2)
C21—N1—C1—C2 −168.62 (15) C7—C8—C15—C16 110.44 (17)
C8—N1—C1—C2 1.50 (19) N1—C8—C15—C20 46.1 (2)
O1—C1—C2—C7 −179.92 (18) C9—C8—C15—C20 170.38 (15)
N1—C1—C2—C7 −0.79 (19) C7—C8—C15—C20 −64.54 (19)
O1—C1—C2—C3 −5.3 (3) C10—O2—C16—C15 9.4 (2)
N1—C1—C2—C3 173.79 (18) C10—O2—C16—C17 −170.81 (14)
C7—C2—C3—C4 −0.1 (3) C20—C15—C16—O2 179.04 (15)
C1—C2—C3—C4 −174.11 (18) C8—C15—C16—O2 3.7 (2)
C2—C3—C4—C5 −0.4 (3) C20—C15—C16—C17 −0.8 (2)
C3—C4—C5—C6 0.0 (3) C8—C15—C16—C17 −176.08 (15)
C4—C5—C6—C7 0.9 (3) O2—C16—C17—C18 −179.34 (15)
C5—C6—C7—C2 −1.4 (3) C15—C16—C17—C18 0.5 (3)
C5—C6—C7—C8 174.27 (18) C16—C17—C18—N4 −179.84 (16)
C3—C2—C7—C6 1.0 (3) C16—C17—C18—C19 −0.4 (3)
C1—C2—C7—C6 176.16 (16) C36—N4—C18—C17 −13.2 (3)
C3—C2—C7—C8 −175.35 (16) C34—N4—C18—C17 −170.6 (2)
C1—C2—C7—C8 −0.18 (19) C34'—N4—C18—C17 141.0 (5)
C1—N1—C8—C15 −118.30 (15) C36—N4—C18—C19 167.39 (18)
C21—N1—C8—C15 52.0 (2) C34—N4—C18—C19 10.0 (3)
C1—N1—C8—C9 118.08 (15) C34'—N4—C18—C19 −38.4 (5)
C21—N1—C8—C9 −71.67 (19) C17—C18—C19—C20 0.7 (3)
C1—N1—C8—C7 −1.53 (17) N4—C18—C19—C20 −179.88 (18)
C21—N1—C8—C7 168.72 (15) C18—C19—C20—C15 −1.1 (3)
C6—C7—C8—N1 −175.03 (17) C16—C15—C20—C19 1.1 (3)
C2—C7—C8—N1 0.97 (17) C8—C15—C20—C19 176.36 (16)
C6—C7—C8—C15 −57.2 (2) C1—N1—C21—C22 −94.8 (2)
C2—C7—C8—C15 118.84 (15) C8—N1—C21—C22 95.9 (2)
C6—C7—C8—C9 66.4 (2) C23—N2—C22—C21 −135.87 (19)
C2—C7—C8—C9 −117.58 (15) N1—C21—C22—N2 −175.59 (14)
N1—C8—C9—C10 138.75 (15) C22—N2—C23—C24 −178.91 (17)
C15—C8—C9—C10 14.3 (2) N2—C23—C24—C29 −178.3 (2)
C7—C8—C9—C10 −109.32 (17) N2—C23—C24—C25 1.7 (3)
N1—C8—C9—C14 −43.2 (2) C29—C24—C25—C26 0.7 (3)
C15—C8—C9—C14 −167.67 (14) C23—C24—C25—C26 −179.25 (17)
C7—C8—C9—C14 68.73 (19) C24—C25—C26—C27 −1.6 (3)
C16—O2—C10—C9 −9.7 (2) C25—C26—C27—C28 1.1 (4)
C16—O2—C10—C11 169.93 (14) C26—C27—C28—C29 0.2 (4)
C14—C9—C10—O2 178.82 (15) C25—C24—C29—C28 0.6 (3)
C8—C9—C10—O2 −3.0 (2) C23—C24—C29—C28 −179.4 (2)
C14—C9—C10—C11 −0.8 (2) C27—C28—C29—C24 −1.0 (4)
C8—C9—C10—C11 177.40 (15) C12—N3—C30—C31 −97.3 (2)
O2—C10—C11—C12 −178.66 (15) C32—N3—C30—C31 95.2 (2)
C9—C10—C11—C12 1.0 (3) C12—N3—C32—C33 −84.8 (2)
C30—N3—C12—C11 −161.22 (18) C30—N3—C32—C33 82.9 (2)
C32—N3—C12—C11 5.9 (3) C18—N4—C34—C35 −153.8 (3)
C30—N3—C12—C13 19.7 (3) C36—N4—C34—C35 49.1 (4)
C32—N3—C12—C13 −173.26 (17) C34'—N4—C34—C35 −42.0 (6)
C10—C11—C12—N3 −178.91 (17) C18—N4—C34'—C35' 128.0 (7)
C10—C11—C12—C13 0.3 (3) C36—N4—C34'—C35' −76.5 (9)
N3—C12—C13—C14 177.52 (17) C34—N4—C34'—C35' 33.5 (7)
C11—C12—C13—C14 −1.6 (3) C18—N4—C36—C37 87.3 (2)
C12—C13—C14—C9 1.9 (3) C34—N4—C36—C37 −115.6 (2)
C10—C9—C14—C13 −0.7 (3) C34'—N4—C36—C37 −69.9 (5)
C8—C9—C14—C13 −178.82 (16)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2398).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811020320/bg2398sup1.cif

e-67-o1733-sup1.cif (30.3KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020320/bg2398Isup2.hkl

e-67-o1733-Isup2.hkl (301.9KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811020320/bg2398Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811020320/bg2398Isup4.cml

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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