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The title compound, C33H28IN5O6, is a mol­ecular clip based on the glycoluril framework. A 4-pyridinylethynyl-substituted benzene ring is fused to one seven-membered ring, which binds two of the N atoms from separate rings of the glycoluril system. The second, similar, seven-membered ring is fused to an iodo­benzene ring. The orientation of these fused-benzene-ring substituents is trans with respect to the glycouril framework. The crystal structure is stabilized by weak C—H...O and C—H...N hydrogen bonds and C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049853/sj2160sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049853/sj2160Isup2.hkl
Contains datablock I

CCDC reference: 630475

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.011 Å
  • Disorder in main residue
  • R factor = 0.094
  • wR factor = 0.278
  • Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.26 Ratio
Author Response: This is the result of the disorder in the molecule and attempts to further resolve this were unsuccessful.

Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.78 Ratio
Alert level C RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.278 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT084_ALERT_2_C High R2 Value .................................. 0.28 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT213_ALERT_2_C Atom O5 has ADP max/min Ratio ............. 3.80 prola PLAT213_ALERT_2_C Atom C17 has ADP max/min Ratio ............. 3.30 prola PLAT220_ALERT_2_C Large Non-Solvent N Ueq(max)/Ueq(min) ... 2.69 Ratio
Author Response: This is the result of the disorder in the molecule and attempts to further resolve this were unsuccessful.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C33
PLAT301_ALERT_3_C Main Residue  Disorder .........................       4.00 Perc.
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         11
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C7     -   C8     ...       1.42 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  I1     ..  O3      ..       3.41 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  I1     ..  O5      ..       3.45 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  I1     ..  N4      ..       3.45 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          7
            C2  -C3  -C6  -C7     -1.00 13.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          8
            C4  -C3  -C6  -C7     18.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          9
            C3  -C6  -C7  -C8      5.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         10
            C6  -C7  -C8  -C9      7.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         11
            C6  -C7  -C8  -C13    11.00  0.00   1.555   1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      30.20 Deg.
              C21  -C20  -C21'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      29.80 Deg.
              H20A -C20  -H20C    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      29.10 Deg.
              H20B -C20  -H20D    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      21.10 Deg.
              C25' -C24  -C25     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      21.30 Deg.
              H24A -C24  -H24C    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      20.40 Deg.
              H24B -C24  -H24D    1.555   1.555   1.555

1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 25 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 16 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Diethyl 4-iodo-1,22-dioxo-15-(4-pyridylethynyl)-1,20,12,21- tetraazahexacyclo[10.10.2.03,8.010,23.014,20.021,24]tetracosa- 3,5,7,14,16,18-hexaene-23,24-dicarboxylate top
Crystal data top
C33H28IN5O6F(000) = 2896
Mr = 717.50Dx = 1.609 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2860 reflections
a = 38.825 (3) Åθ = 2.2–19.5°
b = 8.5516 (6) ŵ = 1.14 mm1
c = 18.8448 (14) ÅT = 298 K
β = 108.773 (1)°Block, colorless
V = 5923.9 (7) Å30.08 × 0.06 × 0.02 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
5005 independent reflections
Radiation source: fine-focus sealed tube2882 reflections with I > 2s(I)
Graphite monochromatorRint = 0.076
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 4646
Tmin = 0.915, Tmax = 0.978k = 1010
19410 measured reflectionsl = 2220
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)] = 0.094Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.278H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.1787P)2]
where P = (Fo2 + 2Fc2)/3
5005 reflections(Δ/σ)max < 0.001
418 parametersΔρmax = 0.97 e Å3
57 restraintsΔρmin = 0.81 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)
C10.5230 (3)0.0223 (12)0.6845 (6)0.054 (3)
H10.50960.11370.68170.064*
C20.5044 (3)0.1109 (13)0.6597 (5)0.052 (3)
H20.47910.10950.64130.062*
C30.52302 (19)0.2499 (8)0.6617 (4)0.0269 (16)
C40.5613 (2)0.2432 (10)0.6932 (4)0.0308 (17)
H40.57560.33240.69760.037*
C50.5769 (2)0.0976 (10)0.7173 (5)0.039 (2)
H50.60210.09450.73820.046*
C60.5043 (2)0.3902 (11)0.6367 (5)0.038 (2)
C70.48622 (19)0.5068 (10)0.6139 (4)0.0297 (17)
C80.4644 (2)0.6403 (9)0.5849 (4)0.0267 (16)
C90.4709 (2)0.7288 (11)0.5293 (5)0.040 (2)
H90.48990.70270.51160.048*
C100.4488 (2)0.8585 (11)0.4997 (5)0.045 (2)
H100.45340.92100.46340.054*
C110.4203 (2)0.8915 (9)0.5252 (5)0.0346 (19)
H110.40480.97410.50380.042*
C120.41373 (18)0.8058 (8)0.5816 (4)0.0242 (15)
C130.43566 (17)0.6779 (8)0.6120 (4)0.0202 (15)
C140.3832 (2)0.8589 (8)0.6096 (5)0.0319 (18)
H14A0.39360.90160.65960.038*
H14B0.36990.94210.57740.038*
C150.43183 (18)0.5855 (8)0.6798 (4)0.0237 (16)
H15A0.44940.50070.69100.028*
H15B0.43830.65460.72290.028*
C160.32424 (17)0.7149 (7)0.5587 (4)0.0181 (14)
C170.3844 (2)0.3827 (8)0.6309 (4)0.0224 (16)
C180.36591 (18)0.6192 (7)0.6693 (4)0.0179 (14)
C190.3700 (2)0.7003 (10)0.7464 (4)0.0304 (18)
C200.3935 (3)0.6967 (11)0.8752 (3)0.062 (3)
H20A0.36960.73020.87490.075*0.62
H20B0.40920.78790.88370.075*0.62
H20C0.37140.67790.88730.075*0.38
H20D0.39690.80880.87320.075*0.38
C210.4087 (3)0.5805 (11)0.9373 (3)0.073 (7)0.62
H21A0.39350.48940.92830.110*0.62
H21B0.40950.62670.98430.110*0.62
H21C0.43290.55130.93910.110*0.62
C21'0.4257 (3)0.6276 (11)0.9353 (3)0.045 (6)0.38
H21D0.41930.52680.94950.068*0.38
H21E0.43260.69540.97820.068*0.38
H21F0.44580.61690.91640.068*0.38
C220.33274 (17)0.5076 (7)0.6435 (4)0.0175 (14)
C230.3149 (2)0.4653 (9)0.7027 (4)0.0270 (17)
C240.3203 (2)0.3184 (9)0.8105 (4)0.052 (2)
H24A0.29560.27920.79250.063*0.73
H24B0.32070.41170.84000.063*0.73
H24C0.29390.32020.79400.063*0.27
H24D0.32910.39660.84950.063*0.27
C250.3454 (2)0.1950 (9)0.8585 (4)0.067 (4)0.73
H25A0.33940.09450.83500.101*0.73
H25B0.34240.19230.90710.101*0.73
H25C0.37020.22020.86360.101*0.73
C25'0.3335 (2)0.1598 (9)0.8421 (4)0.031 (7)0.27
H25D0.32340.08140.80470.046*0.27
H25E0.32600.14020.88510.046*0.27
H25F0.35960.15650.85660.046*0.27
C260.27489 (16)0.5177 (8)0.5318 (4)0.0192 (14)
H26A0.25810.59860.50550.023*
H26B0.26310.45950.56180.023*
C270.3243 (2)0.2450 (8)0.5794 (4)0.0261 (16)
H27A0.30610.22500.60360.031*
H27B0.33880.15080.58380.031*
C280.28146 (18)0.4077 (7)0.4744 (4)0.0194 (14)
C290.30511 (18)0.2780 (8)0.4969 (4)0.0239 (15)
C300.3104 (2)0.1734 (8)0.4440 (4)0.0285 (17)
H300.32590.08810.45950.034*
C310.2924 (2)0.1980 (9)0.3682 (4)0.0332 (18)
H310.29570.12810.33320.040*
C320.2698 (2)0.3237 (10)0.3444 (4)0.0319 (18)
H320.25800.33960.29350.038*
C330.26435 (19)0.4284 (9)0.3970 (4)0.0262 (16)
I10.23245 (2)0.59435 (10)0.35853 (4)0.0780 (4)
N10.5599 (2)0.0326 (9)0.7135 (4)0.049 (2)
N20.35762 (15)0.7339 (6)0.6118 (3)0.0238 (13)
N30.39608 (14)0.5198 (6)0.6708 (3)0.0183 (12)
N40.30703 (15)0.5920 (6)0.5818 (3)0.0207 (13)
N50.34762 (16)0.3699 (6)0.6187 (3)0.0211 (13)
O10.31109 (13)0.7939 (6)0.5033 (3)0.0303 (12)
O20.40295 (14)0.2875 (6)0.6130 (3)0.0315 (12)
O30.35480 (18)0.8217 (9)0.7484 (4)0.063 (2)
O40.39085 (17)0.6260 (7)0.8023 (3)0.0412 (14)
O50.28905 (19)0.5306 (10)0.7082 (4)0.064 (2)
O60.33296 (15)0.3556 (7)0.7470 (3)0.0374 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.072 (7)0.040 (5)0.051 (6)0.022 (5)0.023 (5)0.016 (5)
C20.037 (5)0.079 (8)0.037 (5)0.019 (5)0.007 (4)0.016 (5)
C30.027 (4)0.032 (4)0.022 (4)0.007 (3)0.009 (3)0.004 (3)
C40.029 (4)0.041 (5)0.022 (4)0.004 (3)0.008 (3)0.001 (3)
C50.034 (4)0.054 (6)0.024 (4)0.009 (4)0.005 (4)0.002 (4)
C60.029 (4)0.061 (6)0.028 (4)0.005 (4)0.015 (4)0.003 (4)
C70.019 (4)0.048 (5)0.023 (4)0.009 (4)0.008 (3)0.001 (4)
C80.025 (4)0.039 (4)0.018 (4)0.004 (3)0.008 (3)0.007 (3)
C90.029 (4)0.055 (5)0.039 (5)0.008 (4)0.016 (4)0.001 (4)
C100.051 (5)0.063 (6)0.029 (5)0.009 (5)0.023 (4)0.010 (4)
C110.037 (4)0.034 (4)0.030 (4)0.005 (3)0.006 (4)0.006 (3)
C120.021 (4)0.032 (4)0.017 (4)0.003 (3)0.003 (3)0.001 (3)
C130.017 (3)0.026 (4)0.017 (3)0.001 (3)0.004 (3)0.002 (3)
C140.026 (4)0.024 (4)0.050 (5)0.004 (3)0.018 (4)0.005 (4)
C150.015 (3)0.041 (4)0.015 (3)0.008 (3)0.004 (3)0.002 (3)
C160.017 (3)0.017 (3)0.020 (3)0.007 (2)0.007 (2)0.003 (2)
C170.032 (4)0.024 (4)0.010 (3)0.015 (3)0.005 (3)0.010 (3)
C180.021 (3)0.022 (3)0.011 (3)0.011 (3)0.007 (3)0.000 (3)
C190.022 (4)0.042 (5)0.027 (4)0.002 (3)0.008 (3)0.012 (4)
C200.084 (7)0.075 (7)0.027 (5)0.007 (6)0.017 (5)0.013 (5)
C210.098 (9)0.092 (9)0.086 (9)0.002 (6)0.028 (6)0.009 (6)
C21'0.044 (9)0.058 (10)0.035 (9)0.004 (8)0.014 (7)0.002 (8)
C220.021 (3)0.016 (3)0.015 (3)0.011 (3)0.005 (3)0.003 (3)
C230.032 (4)0.037 (4)0.013 (4)0.000 (3)0.007 (3)0.002 (3)
C240.057 (4)0.063 (4)0.043 (4)0.003 (4)0.023 (3)0.012 (3)
C250.078 (8)0.069 (8)0.060 (7)0.011 (7)0.029 (6)0.012 (6)
C25'0.046 (11)0.028 (10)0.016 (10)0.012 (8)0.007 (8)0.002 (8)
C260.007 (3)0.032 (4)0.016 (3)0.004 (3)0.001 (3)0.004 (3)
C270.041 (4)0.013 (3)0.021 (4)0.010 (3)0.007 (3)0.006 (3)
C280.019 (3)0.020 (3)0.020 (4)0.006 (3)0.007 (3)0.005 (3)
C290.027 (4)0.018 (3)0.028 (4)0.003 (3)0.010 (3)0.006 (3)
C300.036 (4)0.023 (4)0.033 (4)0.006 (3)0.020 (4)0.007 (3)
C310.045 (5)0.030 (4)0.026 (4)0.000 (4)0.014 (4)0.014 (3)
C320.037 (4)0.046 (5)0.018 (4)0.001 (4)0.017 (3)0.002 (3)
C330.022 (4)0.037 (4)0.025 (4)0.000 (3)0.015 (3)0.004 (3)
I10.0759 (6)0.0934 (7)0.0608 (6)0.0304 (4)0.0167 (4)0.0124 (4)
N10.069 (6)0.030 (4)0.048 (5)0.007 (4)0.020 (4)0.000 (3)
N20.025 (3)0.017 (3)0.030 (3)0.009 (2)0.010 (3)0.008 (2)
N30.017 (3)0.023 (3)0.014 (3)0.012 (2)0.004 (2)0.007 (2)
N40.026 (3)0.021 (3)0.013 (3)0.013 (2)0.004 (2)0.000 (2)
N50.024 (3)0.019 (3)0.021 (3)0.011 (2)0.008 (2)0.002 (2)
O10.035 (3)0.031 (3)0.025 (3)0.007 (2)0.009 (2)0.010 (2)
O20.035 (3)0.034 (3)0.025 (3)0.023 (2)0.009 (2)0.005 (2)
O30.062 (4)0.079 (5)0.046 (4)0.028 (4)0.015 (3)0.030 (4)
O40.062 (4)0.048 (3)0.015 (3)0.009 (3)0.014 (3)0.004 (2)
O50.068 (4)0.102 (5)0.044 (4)0.052 (4)0.047 (4)0.034 (4)
O60.035 (3)0.050 (3)0.037 (3)0.013 (3)0.024 (3)0.027 (3)
Geometric parameters (Å, º) top
C1—C21.348 (15)C20—H20B0.9700
C1—N11.364 (13)C20—H20C0.9700
C1—H10.9300C20—H20D0.9700
C2—C31.385 (13)C21—H21A0.9600
C2—H20.9300C21—H21B0.9600
C3—C61.403 (12)C21—H21C0.9600
C3—C41.415 (10)C21'—H21D0.9600
C4—C51.395 (11)C21'—H21E0.9600
C4—H40.9300C21'—H21F0.9600
C5—N11.285 (11)C22—N51.453 (8)
C5—H50.9300C22—N41.458 (8)
C6—C71.216 (12)C22—C231.534 (10)
C7—C81.421 (11)C23—O51.181 (10)
C8—C91.381 (12)C23—O61.300 (9)
C8—C131.406 (10)C24—O61.469 (6)
C9—C101.404 (13)C24—C25'1.5030
C9—H90.9300C24—C251.5208
C10—C111.370 (13)C24—H24A0.9700
C10—H100.9300C24—H24B0.9700
C11—C121.381 (11)C24—H24C0.9700
C11—H110.9300C24—H24D0.9700
C12—C131.391 (10)C25—H25A0.9600
C12—C141.514 (10)C25—H25B0.9600
C13—C151.550 (10)C25—H25C0.9600
C14—N21.468 (10)C25'—H25D0.9600
C14—H14A0.9700C25'—H25E0.9600
C14—H14B0.9700C25'—H25F0.9600
C15—N31.456 (9)C26—N41.446 (8)
C15—H15A0.9700C26—C281.517 (9)
C15—H15B0.9700C26—H26A0.9700
C16—O11.209 (8)C26—H26B0.9700
C16—N21.369 (9)C27—N51.441 (9)
C16—N41.388 (9)C27—C291.519 (10)
C17—O21.204 (8)C27—H27A0.9700
C17—N51.377 (10)C27—H27B0.9700
C17—N31.388 (9)C28—C331.406 (10)
C18—N21.421 (9)C28—C291.415 (9)
C18—N31.440 (8)C29—C301.404 (10)
C18—C221.550 (10)C30—C311.390 (11)
C18—C191.571 (10)C30—H300.9300
C19—O31.201 (10)C31—C321.368 (11)
C19—O41.273 (9)C31—H310.9300
C20—O41.474 (8)C32—C331.400 (11)
C20—C211.5038C32—H320.9300
C20—C21'1.5111C33—I11.870 (7)
C20—H20A0.9700
C2—C1—N1124.7 (9)H21D—C21'—H21E109.5
C2—C1—H1117.6C20—C21'—H21F109.5
N1—C1—H1117.6H21D—C21'—H21F109.5
C1—C2—C3119.9 (9)H21E—C21'—H21F109.5
C1—C2—H2120.0N5—C22—N4112.7 (5)
C3—C2—H2120.0N5—C22—C23111.3 (5)
C2—C3—C6121.1 (8)N4—C22—C23110.1 (5)
C2—C3—C4116.5 (7)N5—C22—C18102.9 (5)
C6—C3—C4122.4 (7)N4—C22—C18103.4 (5)
C5—C4—C3117.4 (8)C23—C22—C18116.2 (5)
C5—C4—H4121.3O5—C23—O6125.7 (7)
C3—C4—H4121.3O5—C23—C22123.2 (7)
N1—C5—C4126.4 (8)O6—C23—C22111.0 (6)
N1—C5—H5116.8O6—C24—C25'110.9 (3)
C4—C5—H5116.8O6—C24—C25108.5 (3)
C7—C6—C3176.1 (8)C25'—C24—C2521.1
C6—C7—C8178.0 (9)O6—C24—H24A110.0
C9—C8—C13120.7 (7)C25'—C24—H24A90.0
C9—C8—C7120.0 (7)C25—C24—H24A110.0
C13—C8—C7119.2 (7)O6—C24—H24B110.0
C8—C9—C10119.8 (7)C25'—C24—H24B125.1
C8—C9—H9120.1C25—C24—H24B110.0
C10—C9—H9120.1H24A—C24—H24B108.4
C11—C10—C9119.0 (8)O6—C24—H24C109.3
C11—C10—H10120.5C25'—C24—H24C109.3
C9—C10—H10120.5C25—C24—H24C127.6
C10—C11—C12122.0 (7)H24A—C24—H24C21.3
C10—C11—H11119.0H24B—C24—H24C89.4
C12—C11—H11119.0O6—C24—H24D109.8
C11—C12—C13119.6 (7)C25'—C24—H24D109.3
C11—C12—C14117.9 (7)C25—C24—H24D91.5
C13—C12—C14122.5 (6)H24A—C24—H24D124.8
C12—C13—C8118.9 (6)H24B—C24—H24D20.4
C12—C13—C15122.1 (6)H24C—C24—H24D108.0
C8—C13—C15118.7 (6)C24—C25—H25A109.5
N2—C14—C12113.8 (6)C24—C25—H25B109.5
N2—C14—H14A108.8C24—C25—H25C109.5
C12—C14—H14A108.8C24—C25'—H25D109.5
N2—C14—H14B108.8C24—C25'—H25E109.5
C12—C14—H14B108.8H25D—C25'—H25E109.5
H14A—C14—H14B107.7C24—C25'—H25F109.5
N3—C15—C13116.2 (5)H25D—C25'—H25F109.5
N3—C15—H15A108.2H25E—C25'—H25F109.5
C13—C15—H15A108.2N4—C26—C28115.4 (5)
N3—C15—H15B108.2N4—C26—H26A108.4
C13—C15—H15B108.2C28—C26—H26A108.4
H15A—C15—H15B107.4N4—C26—H26B108.4
O1—C16—N2127.0 (6)C28—C26—H26B108.4
O1—C16—N4125.5 (6)H26A—C26—H26B107.5
N2—C16—N4107.4 (5)N5—C27—C29114.1 (6)
O2—C17—N5125.5 (7)N5—C27—H27A108.7
O2—C17—N3127.1 (7)C29—C27—H27A108.7
N5—C17—N3107.3 (6)N5—C27—H27B108.7
N2—C18—N3113.9 (5)C29—C27—H27B108.7
N2—C18—C22103.0 (5)H27A—C27—H27B107.6
N3—C18—C22103.4 (5)C33—C28—C29117.1 (6)
N2—C18—C19109.3 (5)C33—C28—C26122.0 (6)
N3—C18—C19113.7 (5)C29—C28—C26120.9 (6)
C22—C18—C19112.9 (5)C30—C29—C28121.0 (7)
O3—C19—O4126.4 (7)C30—C29—C27118.3 (6)
O3—C19—C18120.4 (7)C28—C29—C27120.7 (6)
O4—C19—C18113.2 (6)C31—C30—C29119.6 (7)
O4—C20—C21110.3 (4)C31—C30—H30120.2
O4—C20—C21'109.4 (4)C29—C30—H30120.2
C21—C20—C21'30.2C32—C31—C30120.9 (7)
O4—C20—H20A109.6C32—C31—H31119.6
C21—C20—H20A109.6C30—C31—H31119.6
C21'—C20—H20A132.8C31—C32—C33119.8 (7)
O4—C20—H20B109.6C31—C32—H32120.1
C21—C20—H20B109.6C33—C32—H32120.1
C21'—C20—H20B82.4C32—C33—C28121.7 (7)
H20A—C20—H20B108.1C32—C33—I1116.3 (6)
O4—C20—H20C110.4C28—C33—I1122.1 (5)
C21—C20—H20C82.1C5—N1—C1115.0 (8)
C21'—C20—H20C109.9C16—N2—C18113.9 (6)
H20A—C20—H20C29.8C16—N2—C14123.8 (6)
H20B—C20—H20C130.5C18—N2—C14122.3 (6)
O4—C20—H20D109.8C17—N3—C18111.5 (5)
C21—C20—H20D131.3C17—N3—C15121.4 (6)
C21'—C20—H20D109.1C18—N3—C15120.9 (5)
H20A—C20—H20D81.3C16—N4—C26122.0 (5)
H20B—C20—H20D29.1C16—N4—C22110.5 (5)
H20C—C20—H20D108.3C26—N4—C22121.8 (5)
C20—C21—H21A109.5C17—N5—C27126.2 (6)
C20—C21—H21B109.5C17—N5—C22112.4 (6)
C20—C21—H21C109.5C27—N5—C22121.1 (6)
C20—C21'—H21D109.5C19—O4—C20113.7 (6)
C20—C21'—H21E109.5C23—O6—C24115.2 (5)
N1—C1—C2—C30.9 (15)C31—C32—C33—I1179.2 (6)
C1—C2—C3—C6179.6 (8)C29—C28—C33—C321.4 (10)
C1—C2—C3—C42.3 (13)C26—C28—C33—C32178.1 (7)
C2—C3—C4—C51.7 (11)C29—C28—C33—I1179.9 (5)
C6—C3—C4—C5178.9 (7)C26—C28—C33—I10.6 (10)
C3—C4—C5—N10.4 (13)C4—C5—N1—C11.8 (13)
C2—C3—C6—C71 (13)C2—C1—N1—C51.1 (14)
C4—C3—C6—C7179 (100)O1—C16—N2—C18178.2 (6)
C3—C6—C7—C852 (32)N4—C16—N2—C184.9 (7)
C6—C7—C8—C973 (24)O1—C16—N2—C140.7 (10)
C6—C7—C8—C13105 (24)N4—C16—N2—C14176.3 (6)
C13—C8—C9—C100.4 (12)N3—C18—N2—C16115.0 (6)
C7—C8—C9—C10178.6 (8)C22—C18—N2—C163.8 (7)
C8—C9—C10—C112.1 (13)C19—C18—N2—C16116.5 (6)
C9—C10—C11—C123.3 (13)N3—C18—N2—C1463.9 (8)
C10—C11—C12—C132.7 (12)C22—C18—N2—C14175.1 (6)
C10—C11—C12—C14175.6 (8)C19—C18—N2—C1464.6 (8)
C11—C12—C13—C80.9 (10)C12—C14—N2—C16101.3 (8)
C14—C12—C13—C8177.3 (7)C12—C14—N2—C1877.5 (9)
C11—C12—C13—C15174.7 (7)O2—C17—N3—C18168.8 (6)
C14—C12—C13—C153.5 (10)N5—C17—N3—C1814.7 (7)
C9—C8—C13—C120.2 (10)O2—C17—N3—C1516.2 (10)
C7—C8—C13—C12178.0 (7)N5—C17—N3—C15167.2 (5)
C9—C8—C13—C15173.9 (7)N2—C18—N3—C1794.5 (7)
C7—C8—C13—C157.9 (10)C22—C18—N3—C1716.5 (7)
C11—C12—C14—N2129.3 (7)C19—C18—N3—C17139.3 (6)
C13—C12—C14—N252.4 (10)N2—C18—N3—C1558.2 (8)
C12—C13—C15—N357.1 (9)C22—C18—N3—C15169.2 (5)
C8—C13—C15—N3129.1 (7)C19—C18—N3—C1568.0 (8)
N2—C18—C19—O325.6 (10)C13—C15—N3—C1779.0 (7)
N3—C18—C19—O3154.2 (8)C13—C15—N3—C1871.0 (8)
C22—C18—C19—O388.4 (9)O1—C16—N4—C2616.9 (9)
N2—C18—C19—O4153.2 (6)N2—C16—N4—C26166.1 (5)
N3—C18—C19—O424.6 (9)O1—C16—N4—C22170.8 (6)
C22—C18—C19—O492.8 (7)N2—C16—N4—C2212.2 (7)
N2—C18—C22—N5107.1 (5)C28—C26—N4—C1675.6 (7)
N3—C18—C22—N511.8 (6)C28—C26—N4—C2275.4 (8)
C19—C18—C22—N5135.1 (6)N5—C22—N4—C1696.4 (6)
N2—C18—C22—N410.3 (6)C23—C22—N4—C16138.8 (6)
N3—C18—C22—N4129.2 (5)C18—C22—N4—C1614.0 (6)
C19—C18—C22—N4107.5 (6)N5—C22—N4—C2657.6 (8)
N2—C18—C22—C23131.1 (6)C23—C22—N4—C2667.2 (7)
N3—C18—C22—C23110.1 (6)C18—C22—N4—C26168.0 (5)
C19—C18—C22—C2313.3 (8)O2—C17—N5—C273.3 (11)
N5—C22—C23—O5146.3 (8)N3—C17—N5—C27179.9 (6)
N4—C22—C23—O520.7 (10)O2—C17—N5—C22177.3 (6)
C18—C22—C23—O596.4 (9)N3—C17—N5—C226.1 (7)
N5—C22—C23—O636.8 (8)C29—C27—N5—C1794.3 (8)
N4—C22—C23—O6162.4 (6)C29—C27—N5—C2279.2 (8)
C18—C22—C23—O680.5 (7)N4—C22—N5—C17114.5 (6)
N4—C26—C28—C33122.6 (7)C23—C22—N5—C17121.3 (6)
N4—C26—C28—C2957.9 (9)C18—C22—N5—C173.8 (7)
C33—C28—C29—C301.4 (10)N4—C22—N5—C2759.8 (8)
C26—C28—C29—C30178.1 (6)C23—C22—N5—C2764.4 (7)
C33—C28—C29—C27179.0 (6)C18—C22—N5—C27170.5 (5)
C26—C28—C29—C270.5 (10)O3—C19—O4—C204.2 (13)
N5—C27—C29—C30122.6 (7)C18—C19—O4—C20177.2 (7)
N5—C27—C29—C2859.8 (9)C21—C20—O4—C19162.9 (5)
C28—C29—C30—C310.5 (11)C21'—C20—O4—C19165.0 (5)
C27—C29—C30—C31178.1 (7)O5—C23—O6—C243.0 (12)
C29—C30—C31—C320.6 (12)C22—C23—O6—C24173.8 (6)
C30—C31—C32—C330.7 (12)C25'—C24—O6—C23160.6 (5)
C31—C32—C33—C280.3 (11)C25—C24—O6—C23177.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C26—H26A···I10.972.623.217 (7)120
C14—H14A···N1i0.972.553.480 (12)160
C25—H25B···O1ii0.962.493.403 (8)159
C32—H32···O5iii0.932.553.153 (10)123
Symmetry codes: (i) x+1, y+1, z+3/2; (ii) x, y+1, z+1/2; (iii) x, y+1, z1/2.
 

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