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The title compound, C30H36N6O6, is a glycoluril derivative with two ethyl acetate substituents on the convex face of the glycouril system. Two equivalent six-membered triazine rings bind the N atoms from separate rings of the glycouril unit to form the flexible sidewalls of a mol­ecular clip. One N atom from each ring caries a 4-methyl­benzyl substituent. The crystal structure is stabilized by inter­molecular C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046927/sj2153sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046927/sj2153Isup2.hkl
Contains datablock I

CCDC reference: 630471

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.064
  • wR factor = 0.197
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C29' PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C27'
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.22 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.52 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C28' PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C19 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C19' PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24' PLAT301_ALERT_3_C Main Residue Disorder ......................... 19.00 Perc. PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C1 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 30.50 Deg. C19' -O6 -C19 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Diethyl 2,6-bis(4-methylbenzyl)-4,8-dioxo 2,3,6,7-tetrahydro-1H,5H-2,3a,4a,6,7a,8a- hexaazacyclopenta[def]fluorene-8 b,8c-dicarboxylate top
Crystal data top
C30H36N6O6F(000) = 1224
Mr = 576.65Dx = 1.284 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5736 reflections
a = 16.9160 (8) Åθ = 2.4–22.3°
b = 13.6411 (6) ŵ = 0.09 mm1
c = 12.9597 (2) ÅT = 292 K
β = 94.160 (1)°Block, colorless
V = 2982.6 (2) Å30.30 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
3764 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.068
Graphite monochromatorθmax = 27.0°, θmin = 1.9°
φ and ω scansh = 2121
33094 measured reflectionsk = 1717
6504 independent reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197H-atom parameters constrained
S = 1.01 Please provide
6504 reflections(Δ/σ)max < 0.001
455 parametersΔρmax = 0.30 e Å3
95 restraintsΔρmin = 0.24 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.1488 (2)0.6114 (3)1.2997 (3)0.1216 (13)
H1A0.19290.62561.34810.182*
H1B0.12470.55081.31830.182*
H1C0.11060.66341.30080.182*
C20.17739 (17)0.6025 (2)1.1916 (3)0.0825 (8)
C30.16737 (18)0.5161 (2)1.1373 (3)0.0910 (9)
H30.14310.46321.16730.109*
C40.21362 (18)0.6775 (2)1.1457 (3)0.0867 (9)
H40.22130.73641.18110.104*
C50.19305 (17)0.5069 (2)1.0380 (3)0.0816 (9)
H50.18480.44821.00240.098*
C60.23943 (17)0.6690 (2)1.0479 (2)0.0796 (8)
H60.26360.72241.01870.095*
C70.23035 (14)0.58301 (18)0.9920 (2)0.0651 (7)
C80.26021 (15)0.5743 (2)0.8853 (2)0.0712 (7)
H8A0.23970.51460.85260.085*
H8B0.24100.62930.84320.085*
C90.38054 (15)0.48046 (19)0.92974 (18)0.0644 (7)
H9A0.35250.46020.98890.077*
H9B0.43570.49050.95340.077*
C100.38210 (15)0.59895 (19)0.7944 (2)0.0683 (7)
H10A0.35480.65630.76530.082*
H10B0.43730.61650.80960.082*
C110.31452 (13)0.33512 (16)0.84443 (18)0.0530 (6)
C120.31140 (13)0.51139 (17)0.64789 (18)0.0550 (6)
C130.40439 (13)0.42510 (16)0.75289 (17)0.0508 (5)
C140.49490 (13)0.41024 (19)0.75826 (17)0.0572 (6)
C150.62090 (14)0.4791 (2)0.7402 (3)0.0865 (9)
H15A0.64220.49540.80960.104*
H15B0.63620.41240.72530.104*
C160.65248 (19)0.5461 (2)0.6658 (3)0.0954 (10)
H16A0.63620.52490.59680.143*
H16B0.70930.54650.67490.143*
H16C0.63270.61100.67650.143*
C170.35785 (12)0.35177 (16)0.67906 (16)0.0492 (5)
C180.40849 (13)0.2853 (2)0.6139 (2)0.0633 (7)
C190.5019 (3)0.2745 (4)0.4962 (5)0.0759 (14)0.68
H19A0.52500.22380.54130.091*0.68
H19B0.47280.24370.43760.091*0.68
C200.5627 (5)0.3386 (5)0.4617 (6)0.112 (2)0.68
H20A0.53850.39610.43060.168*0.68
H20B0.59200.30500.41190.168*0.68
H20C0.59790.35730.51980.168*0.68
C19'0.4942 (5)0.3212 (8)0.4627 (6)0.056 (2)0.32
H19C0.49530.37930.41960.067*0.32
H19D0.47170.26730.42150.067*0.32
C20'0.5755 (5)0.2963 (9)0.5089 (9)0.072 (3)0.32
H20D0.59820.35260.54410.107*0.32
H20E0.60820.27690.45500.107*0.32
H20F0.57200.24340.55720.107*0.32
C210.24081 (14)0.25072 (18)0.6994 (2)0.0642 (7)
H21A0.21190.21900.75200.077*
H21B0.25410.20140.64960.077*
C220.23384 (13)0.3740 (2)0.56892 (18)0.0619 (6)
H22A0.20110.42530.53640.074*
H22B0.24520.32660.51610.074*
C230.1153 (2)0.2968 (3)0.6140 (3)0.0672 (11)0.60
H23A0.11930.24500.56340.081*0.60
H23B0.08840.35160.57910.081*0.60
C240.0637 (3)0.2597 (4)0.6986 (3)0.0674 (17)0.60
C250.0215 (3)0.1727 (4)0.6853 (4)0.086 (2)0.60
H250.02380.13700.62450.103*0.60
C260.0241 (3)0.1390 (4)0.7630 (5)0.087 (2)0.60
H260.05230.08070.75410.105*0.60
C270.0274 (4)0.1923 (5)0.8539 (4)0.094 (2)0.60
C280.0148 (4)0.2794 (4)0.8671 (4)0.098 (2)0.60
H280.01250.31510.92800.118*0.60
C290.0603 (3)0.3131 (4)0.7895 (4)0.090 (2)0.60
H290.08850.37130.79840.108*0.60
C300.0707 (4)0.1486 (7)0.9437 (6)0.122 (3)0.60
H30A0.08910.20060.98580.182*0.60
H30B0.03490.10740.98510.182*0.60
H30C0.11510.11040.91640.182*0.60
C23'0.1344 (3)0.3647 (5)0.6941 (5)0.0688 (16)0.40
H23C0.10490.40720.64520.083*0.40
H23D0.15760.40610.74910.083*0.40
C24'0.0752 (5)0.2963 (6)0.7411 (8)0.077 (3)0.40
C25'0.0443 (5)0.2155 (7)0.6871 (6)0.085 (4)0.40
H25'0.05590.20540.61890.102*0.40
C26'0.0038 (6)0.1498 (7)0.7350 (7)0.104 (4)0.40
H26'0.02450.09570.69880.125*0.40
C27'0.0210 (7)0.1649 (7)0.8367 (8)0.103 (4)0.40
C28'0.0099 (8)0.2456 (8)0.8907 (7)0.149 (6)0.40
H28'0.00160.25580.95890.179*0.40
C29'0.0580 (7)0.3113 (7)0.8428 (7)0.156 (7)0.40
H29'0.07880.36550.87900.187*0.40
C30'0.0766 (9)0.0937 (11)0.8887 (12)0.158 (6)0.40
H30D0.04570.04900.93230.236*0.40
H30E0.10740.05740.83640.236*0.40
H30F0.11150.13010.92960.236*0.40
N10.34768 (12)0.57253 (15)0.89095 (17)0.0653 (6)
N20.37579 (10)0.40206 (14)0.85312 (13)0.0526 (5)
N30.37741 (10)0.52059 (13)0.71721 (14)0.0545 (5)
N40.31281 (10)0.29424 (13)0.74679 (14)0.0521 (5)
N50.30724 (10)0.41589 (13)0.61293 (13)0.0505 (5)
N60.19131 (12)0.32638 (16)0.64762 (17)0.0715 (6)
O10.27191 (10)0.31311 (12)0.91181 (12)0.0680 (5)
O20.26710 (10)0.57730 (12)0.61946 (14)0.0736 (5)
O30.52286 (10)0.33102 (14)0.78115 (16)0.0847 (6)
O40.53408 (9)0.48739 (13)0.73355 (14)0.0717 (5)
O50.40873 (12)0.19732 (16)0.61712 (17)0.0949 (7)
O60.44897 (11)0.33889 (15)0.55302 (14)0.0801 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.117 (3)0.149 (3)0.105 (3)0.036 (2)0.045 (2)0.003 (2)
C20.0678 (18)0.088 (2)0.094 (2)0.0191 (16)0.0206 (16)0.0106 (17)
C30.0750 (19)0.080 (2)0.122 (3)0.0002 (15)0.0369 (19)0.0018 (19)
C40.084 (2)0.081 (2)0.097 (2)0.0011 (16)0.0182 (18)0.0314 (18)
C50.0757 (18)0.0651 (17)0.107 (2)0.0071 (14)0.0242 (17)0.0184 (16)
C60.0794 (19)0.0623 (17)0.099 (2)0.0048 (13)0.0181 (16)0.0141 (15)
C70.0527 (14)0.0611 (15)0.0817 (18)0.0075 (11)0.0069 (13)0.0092 (13)
C80.0620 (16)0.0675 (17)0.0832 (19)0.0090 (12)0.0001 (14)0.0080 (13)
C90.0547 (14)0.0812 (18)0.0564 (14)0.0074 (12)0.0012 (11)0.0058 (13)
C100.0631 (16)0.0620 (15)0.0801 (18)0.0022 (12)0.0071 (13)0.0053 (13)
C110.0472 (12)0.0573 (13)0.0547 (14)0.0125 (11)0.0051 (11)0.0116 (11)
C120.0494 (13)0.0596 (15)0.0569 (13)0.0076 (11)0.0099 (11)0.0148 (11)
C130.0443 (12)0.0547 (13)0.0534 (13)0.0052 (10)0.0043 (10)0.0054 (10)
C140.0466 (13)0.0711 (16)0.0537 (14)0.0062 (12)0.0028 (10)0.0120 (12)
C150.0421 (14)0.109 (2)0.108 (2)0.0052 (14)0.0032 (14)0.0201 (19)
C160.0726 (19)0.103 (2)0.112 (2)0.0251 (17)0.0151 (18)0.000 (2)
C170.0427 (11)0.0522 (12)0.0526 (13)0.0089 (9)0.0042 (10)0.0051 (10)
C180.0460 (13)0.0753 (18)0.0690 (16)0.0089 (12)0.0075 (12)0.0097 (14)
C190.088 (4)0.063 (3)0.082 (3)0.002 (3)0.042 (3)0.005 (2)
C200.107 (5)0.092 (5)0.147 (7)0.016 (4)0.074 (5)0.006 (4)
C19'0.058 (5)0.051 (5)0.062 (6)0.005 (4)0.023 (4)0.003 (4)
C20'0.054 (5)0.083 (8)0.081 (7)0.006 (5)0.024 (5)0.008 (5)
C210.0537 (14)0.0630 (15)0.0757 (16)0.0016 (11)0.0039 (12)0.0042 (12)
C220.0504 (13)0.0806 (17)0.0541 (14)0.0083 (12)0.0002 (11)0.0026 (12)
C230.051 (2)0.086 (3)0.064 (3)0.009 (2)0.003 (2)0.011 (2)
C240.052 (3)0.069 (4)0.079 (4)0.005 (3)0.006 (3)0.019 (3)
C250.081 (4)0.062 (4)0.116 (5)0.013 (3)0.010 (3)0.008 (3)
C260.061 (4)0.086 (4)0.118 (5)0.022 (3)0.022 (4)0.008 (4)
C270.044 (3)0.123 (5)0.115 (5)0.006 (4)0.010 (3)0.030 (4)
C280.091 (4)0.126 (5)0.077 (4)0.013 (4)0.006 (3)0.020 (4)
C290.070 (4)0.101 (5)0.097 (6)0.027 (3)0.010 (3)0.006 (4)
C300.073 (4)0.171 (8)0.123 (6)0.026 (5)0.022 (4)0.038 (5)
C23'0.058 (4)0.071 (4)0.078 (4)0.005 (3)0.003 (3)0.009 (3)
C24'0.054 (5)0.086 (6)0.092 (7)0.006 (4)0.011 (5)0.009 (5)
C25'0.103 (7)0.063 (7)0.092 (6)0.015 (6)0.022 (5)0.009 (5)
C26'0.078 (7)0.103 (7)0.134 (8)0.038 (5)0.030 (6)0.018 (6)
C27'0.068 (7)0.101 (6)0.141 (9)0.006 (5)0.025 (6)0.029 (7)
C28'0.164 (10)0.176 (10)0.112 (8)0.041 (8)0.041 (7)0.022 (7)
C29'0.146 (9)0.190 (10)0.130 (10)0.048 (7)0.007 (8)0.013 (7)
C30'0.115 (9)0.183 (13)0.180 (13)0.014 (9)0.046 (10)0.047 (10)
N10.0574 (12)0.0669 (13)0.0720 (14)0.0034 (10)0.0072 (10)0.0115 (10)
N20.0476 (10)0.0627 (11)0.0476 (10)0.0071 (9)0.0038 (8)0.0026 (9)
N30.0509 (11)0.0518 (11)0.0605 (12)0.0033 (8)0.0022 (9)0.0026 (9)
N40.0488 (10)0.0519 (11)0.0562 (11)0.0044 (8)0.0074 (9)0.0046 (9)
N50.0458 (10)0.0585 (12)0.0474 (10)0.0066 (8)0.0044 (8)0.0039 (8)
N60.0459 (11)0.0917 (16)0.0773 (14)0.0052 (11)0.0064 (10)0.0220 (12)
O10.0681 (11)0.0774 (12)0.0606 (10)0.0014 (9)0.0186 (9)0.0169 (8)
O20.0665 (11)0.0672 (11)0.0858 (13)0.0190 (9)0.0033 (9)0.0195 (9)
O30.0558 (11)0.0869 (14)0.1120 (16)0.0171 (10)0.0110 (10)0.0250 (11)
O40.0461 (9)0.0742 (11)0.0948 (13)0.0022 (8)0.0045 (9)0.0178 (9)
O50.0841 (14)0.0743 (14)0.1276 (18)0.0186 (11)0.0168 (12)0.0280 (12)
O60.0663 (11)0.1049 (14)0.0724 (12)0.0029 (10)0.0273 (10)0.0229 (11)
Geometric parameters (Å, º) top
C1—C21.519 (4)C20—H20A0.9600
C1—H1A0.9600C20—H20B0.9600
C1—H1B0.9600C20—H20C0.9600
C1—H1C0.9600C19'—O61.464 (7)
C2—C41.353 (4)C19'—C20'1.499 (8)
C2—C31.377 (4)C19'—H19C0.9700
C3—C51.393 (4)C19'—H19D0.9700
C3—H30.9300C20'—H20D0.9600
C4—C61.374 (4)C20'—H20E0.9600
C4—H40.9300C20'—H20F0.9600
C5—C71.374 (4)C21—N41.451 (3)
C5—H50.9300C21—N61.461 (3)
C6—C71.381 (4)C21—H21A0.9700
C6—H60.9300C21—H21B0.9700
C7—C81.510 (4)C22—N61.444 (3)
C8—N11.476 (3)C22—N51.446 (3)
C8—H8A0.9700C22—H22A0.9700
C8—H8B0.9700C22—H22B0.9700
C9—N11.449 (3)C23—N61.388 (4)
C9—N21.458 (3)C23—C241.535 (5)
C9—H9A0.9700C23—H23A0.9700
C9—H9B0.9700C23—H23B0.9700
C10—N31.462 (3)C24—C251.389 (3)
C10—N11.464 (3)C24—C291.389 (3)
C10—H10A0.9700C25—C261.389 (3)
C10—H10B0.9700C25—H250.9300
C11—O11.210 (2)C26—C271.389 (3)
C11—N21.380 (3)C26—H260.9300
C11—N41.381 (3)C27—C281.389 (3)
C12—O21.211 (3)C27—C301.540 (6)
C12—N51.379 (3)C28—C291.389 (3)
C12—N31.387 (3)C28—H280.9300
C13—N31.445 (3)C29—H290.9300
C13—N21.453 (3)C30—H30A0.9600
C13—C141.541 (3)C30—H30B0.9600
C13—C171.558 (3)C30—H30C0.9600
C14—O31.208 (3)C23'—N61.283 (6)
C14—O41.296 (3)C23'—C24'1.527 (7)
C15—C161.458 (4)C23'—H23C0.9700
C15—O41.469 (3)C23'—H23D0.9700
C15—H15A0.9700C24'—C25'1.386 (5)
C15—H15B0.9700C24'—C29'1.386 (5)
C16—H16A0.9600C25'—C26'1.386 (5)
C16—H16B0.9600C25'—H25'0.9300
C16—H16C0.9600C26'—C27'1.386 (5)
C17—N41.437 (3)C26'—H26'0.9300
C17—N51.458 (3)C27'—C28'1.386 (5)
C17—C181.541 (3)C27'—C30'1.542 (8)
C18—O51.201 (3)C28'—C29'1.386 (5)
C18—O61.305 (3)C28'—H28'0.9300
C19—C201.444 (5)C29'—H29'0.9300
C19—O61.487 (4)C30'—H30D0.9600
C19—H19A0.9700C30'—H30E0.9600
C19—H19B0.9700C30'—H30F0.9600
C2—C1—H1A109.5H20D—C20'—H20F109.5
C2—C1—H1B109.5H20E—C20'—H20F109.5
H1A—C1—H1B109.5N4—C21—N6109.94 (19)
C2—C1—H1C109.5N4—C21—H21A109.7
H1A—C1—H1C109.5N6—C21—H21A109.7
H1B—C1—H1C109.5N4—C21—H21B109.7
C4—C2—C3117.7 (3)N6—C21—H21B109.7
C4—C2—C1122.0 (3)H21A—C21—H21B108.2
C3—C2—C1120.3 (3)N6—C22—N5110.89 (18)
C2—C3—C5121.0 (3)N6—C22—H22A109.5
C2—C3—H3119.5N5—C22—H22A109.5
C5—C3—H3119.5N6—C22—H22B109.5
C2—C4—C6121.7 (3)N5—C22—H22B109.5
C2—C4—H4119.1H22A—C22—H22B108.0
C6—C4—H4119.1N6—C23—C24115.7 (3)
C7—C5—C3121.1 (3)N6—C23—H23A108.4
C7—C5—H5119.5C24—C23—H23A108.4
C3—C5—H5119.5N6—C23—H23B108.4
C4—C6—C7121.7 (3)C24—C23—H23B108.4
C4—C6—H6119.2H23A—C23—H23B107.4
C7—C6—H6119.2C25—C24—C29120.0
C5—C7—C6116.8 (3)C25—C24—C23120.4 (4)
C5—C7—C8122.2 (2)C29—C24—C23119.6 (4)
C6—C7—C8121.0 (2)C24—C25—C26120.0
N1—C8—C7110.9 (2)C24—C25—H25120.0
N1—C8—H8A109.5C26—C25—H25120.0
C7—C8—H8A109.5C25—C26—C27120.0
N1—C8—H8B109.5C25—C26—H26120.0
C7—C8—H8B109.5C27—C26—H26120.0
H8A—C8—H8B108.1C28—C27—C26120.0
N1—C9—N2113.51 (19)C28—C27—C30120.4 (3)
N1—C9—H9A108.9C26—C27—C30119.3 (3)
N2—C9—H9A108.9C27—C28—C29120.0
N1—C9—H9B108.9C27—C28—H28120.0
N2—C9—H9B108.9C29—C28—H28120.0
H9A—C9—H9B107.7C28—C29—C24120.0
N3—C10—N1113.6 (2)C28—C29—H29120.0
N3—C10—H10A108.9C24—C29—H29120.0
N1—C10—H10A108.9N6—C23'—C24'118.3 (6)
N3—C10—H10B108.9N6—C23'—H23C107.7
N1—C10—H10B108.9C24'—C23'—H23C107.7
H10A—C10—H10B107.7N6—C23'—H23D107.7
O1—C11—N2126.1 (2)C24'—C23'—H23D107.7
O1—C11—N4126.0 (2)H23C—C23'—H23D107.1
N2—C11—N4107.92 (18)C25'—C24'—C29'120.0
O2—C12—N5125.8 (2)C25'—C24'—C23'121.2 (7)
O2—C12—N3125.6 (2)C29'—C24'—C23'118.5 (7)
N5—C12—N3108.52 (18)C24'—C25'—C26'120.0
N3—C13—N2111.30 (17)C24'—C25'—H25'120.0
N3—C13—C14115.01 (18)C26'—C25'—H25'120.0
N2—C13—C14108.99 (17)C25'—C26'—C27'120.0
N3—C13—C17104.39 (17)C25'—C26'—H26'120.0
N2—C13—C17102.95 (17)C27'—C26'—H26'120.0
C14—C13—C17113.54 (18)C28'—C27'—C26'120.0
O3—C14—O4126.1 (2)C28'—C27'—C30'120.0 (4)
O3—C14—C13119.9 (2)C26'—C27'—C30'119.9 (4)
O4—C14—C13114.0 (2)C29'—C28'—C27'120.0
C16—C15—O4109.0 (2)C29'—C28'—H28'120.0
C16—C15—H15A109.9C27'—C28'—H28'120.0
O4—C15—H15A109.9C28'—C29'—C24'120.0
C16—C15—H15B109.9C28'—C29'—H29'120.0
O4—C15—H15B109.9C24'—C29'—H29'120.0
H15A—C15—H15B108.3C27'—C30'—H30D109.5
C15—C16—H16A109.5C27'—C30'—H30E109.5
C15—C16—H16B109.5H30D—C30'—H30E109.5
H16A—C16—H16B109.5C27'—C30'—H30F109.5
C15—C16—H16C109.5H30D—C30'—H30F109.5
H16A—C16—H16C109.5H30E—C30'—H30F109.5
H16B—C16—H16C109.5C9—N1—C10110.11 (18)
N4—C17—N5111.84 (16)C9—N1—C8112.9 (2)
N4—C17—C18110.73 (19)C10—N1—C8114.4 (2)
N5—C17—C18110.91 (18)C11—N2—C13111.53 (18)
N4—C17—C13104.02 (17)C11—N2—C9123.04 (19)
N5—C17—C13102.99 (17)C13—N2—C9116.41 (19)
C18—C17—C13116.00 (18)C12—N3—C13110.27 (18)
O5—C18—O6125.4 (2)C12—N3—C10120.69 (19)
O5—C18—C17124.7 (2)C13—N3—C10116.11 (18)
O6—C18—C17109.8 (2)C11—N4—C17111.25 (18)
C20—C19—O6105.3 (4)C11—N4—C21120.93 (18)
C20—C19—H19A110.7C17—N4—C21115.55 (18)
O6—C19—H19A110.7C12—N5—C22121.67 (19)
C20—C19—H19B110.7C12—N5—C17111.08 (18)
O6—C19—H19B110.7C22—N5—C17116.44 (18)
H19A—C19—H19B108.8C23'—N6—C2363.6 (3)
O6—C19'—C20'103.6 (7)C23'—N6—C22125.3 (3)
O6—C19'—H19C111.0C23—N6—C22114.0 (2)
C20'—C19'—H19C111.0C23'—N6—C21119.8 (4)
O6—C19'—H19D111.0C23—N6—C21115.2 (3)
C20'—C19'—H19D111.0C22—N6—C21110.10 (19)
H19C—C19'—H19D109.0C14—O4—C15116.7 (2)
C19'—C20'—H20D109.5C18—O6—C19'135.9 (5)
C19'—C20'—H20E109.5C18—O6—C19109.3 (3)
H20D—C20'—H20E109.5C19'—O6—C1930.5 (3)
C19'—C20'—H20F109.5
C4—C2—C3—C50.6 (5)N3—C13—N2—C11104.7 (2)
C1—C2—C3—C5179.8 (3)C14—C13—N2—C11127.48 (19)
C3—C2—C4—C60.3 (5)C17—C13—N2—C116.6 (2)
C1—C2—C4—C6179.9 (3)N3—C13—N2—C943.6 (2)
C2—C3—C5—C71.1 (4)C14—C13—N2—C984.3 (2)
C2—C4—C6—C70.6 (5)C17—C13—N2—C9154.89 (17)
C3—C5—C7—C61.3 (4)N1—C9—N2—C1194.5 (3)
C3—C5—C7—C8178.8 (2)N1—C9—N2—C1349.7 (3)
C4—C6—C7—C51.0 (4)O2—C12—N3—C13165.7 (2)
C4—C6—C7—C8179.0 (3)N5—C12—N3—C1317.4 (2)
C5—C7—C8—N1109.7 (3)O2—C12—N3—C1025.8 (3)
C6—C7—C8—N170.4 (3)N5—C12—N3—C10157.26 (19)
N3—C13—C14—O3175.5 (2)N2—C13—N3—C1298.5 (2)
N2—C13—C14—O358.7 (3)C14—C13—N3—C12137.0 (2)
C17—C13—C14—O355.4 (3)C17—C13—N3—C1211.9 (2)
N3—C13—C14—O42.5 (3)N2—C13—N3—C1043.4 (2)
N2—C13—C14—O4123.2 (2)C14—C13—N3—C1081.2 (2)
C17—C13—C14—O4122.7 (2)C17—C13—N3—C10153.78 (18)
N3—C13—C17—N4119.20 (17)N1—C10—N3—C1288.3 (3)
N2—C13—C17—N42.86 (19)N1—C10—N3—C1349.4 (3)
C14—C13—C17—N4114.80 (19)O1—C11—N4—C17166.6 (2)
N3—C13—C17—N52.4 (2)N2—C11—N4—C1716.2 (2)
N2—C13—C17—N5113.95 (16)O1—C11—N4—C2126.0 (3)
C14—C13—C17—N5128.39 (18)N2—C11—N4—C21156.75 (18)
N3—C13—C17—C18118.9 (2)N5—C17—N4—C1198.9 (2)
N2—C13—C17—C18124.7 (2)C18—C17—N4—C11136.85 (18)
C14—C13—C17—C187.1 (3)C13—C17—N4—C1111.6 (2)
N4—C17—C18—O51.9 (3)N5—C17—N4—C2144.0 (2)
N5—C17—C18—O5122.9 (3)C18—C17—N4—C2180.3 (2)
C13—C17—C18—O5120.1 (3)C13—C17—N4—C21154.43 (17)
N4—C17—C18—O6179.94 (18)N6—C21—N4—C1185.3 (2)
N5—C17—C18—O655.3 (2)N6—C21—N4—C1753.7 (3)
C13—C17—C18—O661.7 (3)O2—C12—N5—C2224.3 (3)
N6—C23—C24—C25132.4 (4)N3—C12—N5—C22158.76 (18)
N6—C23—C24—C2946.6 (5)O2—C12—N5—C17167.3 (2)
C29—C24—C25—C260.0N3—C12—N5—C1715.8 (2)
C23—C24—C25—C26179.0 (5)N6—C22—N5—C1291.5 (2)
C24—C25—C26—C270.0N6—C22—N5—C1749.6 (3)
C25—C26—C27—C280.0N4—C17—N5—C12103.2 (2)
C25—C26—C27—C30173.4 (7)C18—C17—N5—C12132.6 (2)
C26—C27—C28—C290.0C13—C17—N5—C127.9 (2)
C30—C27—C28—C29173.3 (7)N4—C17—N5—C2241.9 (2)
C27—C28—C29—C240.0C18—C17—N5—C2282.3 (2)
C25—C24—C29—C280.0C13—C17—N5—C22152.99 (18)
C23—C24—C29—C28179.0 (5)C24'—C23'—N6—C2354.2 (6)
N6—C23'—C24'—C25'44.4 (10)C24'—C23'—N6—C22156.1 (5)
N6—C23'—C24'—C29'130.0 (7)C24'—C23'—N6—C2151.1 (8)
C29'—C24'—C25'—C26'0.0C24—C23—N6—C23'52.4 (5)
C23'—C24'—C25'—C26'174.3 (8)C24—C23—N6—C22171.4 (3)
C24'—C25'—C26'—C27'0.0C24—C23—N6—C2159.9 (5)
C25'—C26'—C27'—C28'0.0N5—C22—N6—C23'97.5 (4)
C25'—C26'—C27'—C30'178.0 (12)N5—C22—N6—C23171.2 (3)
C26'—C27'—C28'—C29'0.0N5—C22—N6—C2157.5 (3)
C30'—C27'—C28'—C29'178.0 (12)N4—C21—N6—C23'97.1 (4)
C27'—C28'—C29'—C24'0.0N4—C21—N6—C23169.9 (3)
C25'—C24'—C29'—C28'0.0N4—C21—N6—C2259.5 (3)
C23'—C24'—C29'—C28'174.5 (8)O3—C14—O4—C154.0 (4)
N2—C9—N1—C1051.7 (3)C13—C14—O4—C15178.1 (2)
N2—C9—N1—C877.5 (3)C16—C15—O4—C14151.8 (3)
N3—C10—N1—C951.7 (3)O5—C18—O6—C19'12.1 (6)
N3—C10—N1—C876.7 (3)C17—C18—O6—C19'166.1 (5)
C7—C8—N1—C973.6 (3)O5—C18—O6—C195.9 (4)
C7—C8—N1—C10159.4 (2)C17—C18—O6—C19175.9 (3)
O1—C11—N2—C13168.7 (2)C20'—C19'—O6—C1887.4 (9)
N4—C11—N2—C1314.1 (2)C20'—C19'—O6—C1952.3 (8)
O1—C11—N2—C922.9 (3)C20—C19—O6—C18159.9 (5)
N4—C11—N2—C9159.90 (18)C20—C19—O6—C19'45.2 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22B···O1i0.972.403.356 (3)169
C19—H19B···O3i0.972.473.179 (5)129
Symmetry code: (i) x, y+1/2, z1/2.
 

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