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: a mol­ecular clip based on bis­(ethoxy­carbon­yl)glycoluril

Chen, Y.-F.; Qin, J.; Cao, L.-P.; Gao, M.

doi:10.1107/S1600536806049853

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Diethyl 4-iodo-1,22-dioxo-15-(4-pyridylethynyl)-1,20,12,21-tetraazahexacyclo[10.10.2.0^3,8.0^10,23.0^14,20.0^21,24]tetracosa-3,5,7,14,16,18-hexaene-23,24-dicarboxylate: a molecular clip based on bis(ethoxycarbonyl)glycoluril

Y.-F. Chen, J. Qin, L.-P. Cao and M. Gao

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049853/sj2160sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049853/sj2160Isup2.hkl Contains datablock I

CCDC reference: 630475

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (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[10.10.2.0^3,8.0^10,23.0^14,20.0^21,24]tetracosa- 3,5,7,14,16,18-hexaene-23,24-dicarboxylate top

Crystal data top

C₃₃H₂₈IN₅O₆	F(000) = 2896
M_r = 717.50	D_x = 1.609 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2860 reflections
a = 38.825 (3) Å	θ = 2.2–19.5°
b = 8.5516 (6) Å	µ = 1.14 mm⁻¹
c = 18.8448 (14) Å	T = 298 K
β = 108.773 (1)°	Block, colorless
V = 5923.9 (7) Å³	0.08 × 0.06 × 0.02 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	5005 independent reflections
Radiation source: fine-focus sealed tube	2882 reflections with I > 2s(I)
Graphite monochromator	R_int = 0.076
φ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −46→46
T_min = 0.915, T_max = 0.978	k = −10→10
19410 measured reflections	l = −22→20

Refinement top

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)] = 0.094	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.278	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.1787P)²] where P = (F_o² + 2F_c²)/3
5005 reflections	(Δ/σ)_max < 0.001
418 parameters	Δρ_max = 0.97 e Å⁻³
57 restraints	Δρ_min = −0.81 e Å⁻³

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.5230 (3)	−0.0223 (12)	0.6845 (6)	0.054 (3)
H1	0.5096	−0.1137	0.6817	0.064*
C2	0.5044 (3)	0.1109 (13)	0.6597 (5)	0.052 (3)
H2	0.4791	0.1095	0.6413	0.062*
C3	0.52302 (19)	0.2499 (8)	0.6617 (4)	0.0269 (16)
C4	0.5613 (2)	0.2432 (10)	0.6932 (4)	0.0308 (17)
H4	0.5756	0.3324	0.6976	0.037*
C5	0.5769 (2)	0.0976 (10)	0.7173 (5)	0.039 (2)
H5	0.6021	0.0945	0.7382	0.046*
C6	0.5043 (2)	0.3902 (11)	0.6367 (5)	0.038 (2)
C7	0.48622 (19)	0.5068 (10)	0.6139 (4)	0.0297 (17)
C8	0.4644 (2)	0.6403 (9)	0.5849 (4)	0.0267 (16)
C9	0.4709 (2)	0.7288 (11)	0.5293 (5)	0.040 (2)
H9	0.4899	0.7027	0.5116	0.048*
C10	0.4488 (2)	0.8585 (11)	0.4997 (5)	0.045 (2)
H10	0.4534	0.9210	0.4634	0.054*
C11	0.4203 (2)	0.8915 (9)	0.5252 (5)	0.0346 (19)
H11	0.4048	0.9741	0.5038	0.042*
C12	0.41373 (18)	0.8058 (8)	0.5816 (4)	0.0242 (15)
C13	0.43566 (17)	0.6779 (8)	0.6120 (4)	0.0202 (15)
C14	0.3832 (2)	0.8589 (8)	0.6096 (5)	0.0319 (18)
H14A	0.3936	0.9016	0.6596	0.038*
H14B	0.3699	0.9421	0.5774	0.038*
C15	0.43183 (18)	0.5855 (8)	0.6798 (4)	0.0237 (16)
H15A	0.4494	0.5007	0.6910	0.028*
H15B	0.4383	0.6546	0.7229	0.028*
C16	0.32424 (17)	0.7149 (7)	0.5587 (4)	0.0181 (14)
C17	0.3844 (2)	0.3827 (8)	0.6309 (4)	0.0224 (16)
C18	0.36591 (18)	0.6192 (7)	0.6693 (4)	0.0179 (14)
C19	0.3700 (2)	0.7003 (10)	0.7464 (4)	0.0304 (18)
C20	0.3935 (3)	0.6967 (11)	0.8752 (3)	0.062 (3)
H20A	0.3696	0.7302	0.8749	0.075*	0.62
H20B	0.4092	0.7879	0.8837	0.075*	0.62
H20C	0.3714	0.6779	0.8873	0.075*	0.38
H20D	0.3969	0.8088	0.8732	0.075*	0.38
C21	0.4087 (3)	0.5805 (11)	0.9373 (3)	0.073 (7)	0.62
H21A	0.3935	0.4894	0.9283	0.110*	0.62
H21B	0.4095	0.6267	0.9843	0.110*	0.62
H21C	0.4329	0.5513	0.9391	0.110*	0.62
C21'	0.4257 (3)	0.6276 (11)	0.9353 (3)	0.045 (6)	0.38
H21D	0.4193	0.5268	0.9495	0.068*	0.38
H21E	0.4326	0.6954	0.9782	0.068*	0.38
H21F	0.4458	0.6169	0.9164	0.068*	0.38
C22	0.33274 (17)	0.5076 (7)	0.6435 (4)	0.0175 (14)
C23	0.3149 (2)	0.4653 (9)	0.7027 (4)	0.0270 (17)
C24	0.3203 (2)	0.3184 (9)	0.8105 (4)	0.052 (2)
H24A	0.2956	0.2792	0.7925	0.063*	0.73
H24B	0.3207	0.4117	0.8400	0.063*	0.73
H24C	0.2939	0.3202	0.7940	0.063*	0.27
H24D	0.3291	0.3966	0.8495	0.063*	0.27
C25	0.3454 (2)	0.1950 (9)	0.8585 (4)	0.067 (4)	0.73
H25A	0.3394	0.0945	0.8350	0.101*	0.73
H25B	0.3424	0.1923	0.9071	0.101*	0.73
H25C	0.3702	0.2202	0.8636	0.101*	0.73
C25'	0.3335 (2)	0.1598 (9)	0.8421 (4)	0.031 (7)	0.27
H25D	0.3234	0.0814	0.8047	0.046*	0.27
H25E	0.3260	0.1402	0.8851	0.046*	0.27
H25F	0.3596	0.1565	0.8566	0.046*	0.27
C26	0.27489 (16)	0.5177 (8)	0.5318 (4)	0.0192 (14)
H26A	0.2581	0.5986	0.5055	0.023*
H26B	0.2631	0.4595	0.5618	0.023*
C27	0.3243 (2)	0.2450 (8)	0.5794 (4)	0.0261 (16)
H27A	0.3061	0.2250	0.6036	0.031*
H27B	0.3388	0.1508	0.5838	0.031*
C28	0.28146 (18)	0.4077 (7)	0.4744 (4)	0.0194 (14)
C29	0.30511 (18)	0.2780 (8)	0.4969 (4)	0.0239 (15)
C30	0.3104 (2)	0.1734 (8)	0.4440 (4)	0.0285 (17)
H30	0.3259	0.0881	0.4595	0.034*
C31	0.2924 (2)	0.1980 (9)	0.3682 (4)	0.0332 (18)
H31	0.2957	0.1281	0.3332	0.040*
C32	0.2698 (2)	0.3237 (10)	0.3444 (4)	0.0319 (18)
H32	0.2580	0.3396	0.2935	0.038*
C33	0.26435 (19)	0.4284 (9)	0.3970 (4)	0.0262 (16)
I1	0.23245 (2)	0.59435 (10)	0.35853 (4)	0.0780 (4)
N1	0.5599 (2)	−0.0326 (9)	0.7135 (4)	0.049 (2)
N2	0.35762 (15)	0.7339 (6)	0.6118 (3)	0.0238 (13)
N3	0.39608 (14)	0.5198 (6)	0.6708 (3)	0.0183 (12)
N4	0.30703 (15)	0.5920 (6)	0.5818 (3)	0.0207 (13)
N5	0.34762 (16)	0.3699 (6)	0.6187 (3)	0.0211 (13)
O1	0.31109 (13)	0.7939 (6)	0.5033 (3)	0.0303 (12)
O2	0.40295 (14)	0.2875 (6)	0.6130 (3)	0.0315 (12)
O3	0.35480 (18)	0.8217 (9)	0.7484 (4)	0.063 (2)
O4	0.39085 (17)	0.6260 (7)	0.8023 (3)	0.0412 (14)
O5	0.28905 (19)	0.5306 (10)	0.7082 (4)	0.064 (2)
O6	0.33296 (15)	0.3556 (7)	0.7470 (3)	0.0374 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.072 (7)	0.040 (5)	0.051 (6)	−0.022 (5)	0.023 (5)	−0.016 (5)
C2	0.037 (5)	0.079 (8)	0.037 (5)	−0.019 (5)	0.007 (4)	−0.016 (5)
C3	0.027 (4)	0.032 (4)	0.022 (4)	0.007 (3)	0.009 (3)	−0.004 (3)
C4	0.029 (4)	0.041 (5)	0.022 (4)	0.004 (3)	0.008 (3)	−0.001 (3)
C5	0.034 (4)	0.054 (6)	0.024 (4)	0.009 (4)	0.005 (4)	−0.002 (4)
C6	0.029 (4)	0.061 (6)	0.028 (4)	−0.005 (4)	0.015 (4)	−0.003 (4)
C7	0.019 (4)	0.048 (5)	0.023 (4)	0.009 (4)	0.008 (3)	0.001 (4)
C8	0.025 (4)	0.039 (4)	0.018 (4)	0.004 (3)	0.008 (3)	−0.007 (3)
C9	0.029 (4)	0.055 (5)	0.039 (5)	0.008 (4)	0.016 (4)	−0.001 (4)
C10	0.051 (5)	0.063 (6)	0.029 (5)	−0.009 (5)	0.023 (4)	0.010 (4)
C11	0.037 (4)	0.034 (4)	0.030 (4)	0.005 (3)	0.006 (4)	0.006 (3)
C12	0.021 (4)	0.032 (4)	0.017 (4)	−0.003 (3)	0.003 (3)	0.001 (3)
C13	0.017 (3)	0.026 (4)	0.017 (3)	−0.001 (3)	0.004 (3)	0.002 (3)
C14	0.026 (4)	0.024 (4)	0.050 (5)	0.004 (3)	0.018 (4)	−0.005 (4)
C15	0.015 (3)	0.041 (4)	0.015 (3)	0.008 (3)	0.004 (3)	0.002 (3)
C16	0.017 (3)	0.017 (3)	0.020 (3)	0.007 (2)	0.007 (2)	−0.003 (2)
C17	0.032 (4)	0.024 (4)	0.010 (3)	0.015 (3)	0.005 (3)	0.010 (3)
C18	0.021 (3)	0.022 (3)	0.011 (3)	0.011 (3)	0.007 (3)	0.000 (3)
C19	0.022 (4)	0.042 (5)	0.027 (4)	0.002 (3)	0.008 (3)	−0.012 (4)
C20	0.084 (7)	0.075 (7)	0.027 (5)	0.007 (6)	0.017 (5)	−0.013 (5)
C21	0.098 (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)
C22	0.021 (3)	0.016 (3)	0.015 (3)	0.011 (3)	0.005 (3)	0.003 (3)
C23	0.032 (4)	0.037 (4)	0.013 (4)	0.000 (3)	0.007 (3)	−0.002 (3)
C24	0.057 (4)	0.063 (4)	0.043 (4)	−0.003 (4)	0.023 (3)	0.012 (3)
C25	0.078 (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)
C26	0.007 (3)	0.032 (4)	0.016 (3)	0.004 (3)	0.001 (3)	−0.004 (3)
C27	0.041 (4)	0.013 (3)	0.021 (4)	0.010 (3)	0.007 (3)	0.006 (3)
C28	0.019 (3)	0.020 (3)	0.020 (4)	0.006 (3)	0.007 (3)	0.005 (3)
C29	0.027 (4)	0.018 (3)	0.028 (4)	−0.003 (3)	0.010 (3)	−0.006 (3)
C30	0.036 (4)	0.023 (4)	0.033 (4)	0.006 (3)	0.020 (4)	−0.007 (3)
C31	0.045 (5)	0.030 (4)	0.026 (4)	0.000 (4)	0.014 (4)	−0.014 (3)
C32	0.037 (4)	0.046 (5)	0.018 (4)	−0.001 (4)	0.017 (3)	−0.002 (3)
C33	0.022 (4)	0.037 (4)	0.025 (4)	0.000 (3)	0.015 (3)	−0.004 (3)
I1	0.0759 (6)	0.0934 (7)	0.0608 (6)	0.0304 (4)	0.0167 (4)	0.0124 (4)
N1	0.069 (6)	0.030 (4)	0.048 (5)	0.007 (4)	0.020 (4)	0.000 (3)
N2	0.025 (3)	0.017 (3)	0.030 (3)	0.009 (2)	0.010 (3)	0.008 (2)
N3	0.017 (3)	0.023 (3)	0.014 (3)	0.012 (2)	0.004 (2)	0.007 (2)
N4	0.026 (3)	0.021 (3)	0.013 (3)	0.013 (2)	0.004 (2)	0.000 (2)
N5	0.024 (3)	0.019 (3)	0.021 (3)	0.011 (2)	0.008 (2)	0.002 (2)
O1	0.035 (3)	0.031 (3)	0.025 (3)	0.007 (2)	0.009 (2)	0.010 (2)
O2	0.035 (3)	0.034 (3)	0.025 (3)	0.023 (2)	0.009 (2)	0.005 (2)
O3	0.062 (4)	0.079 (5)	0.046 (4)	0.028 (4)	0.015 (3)	−0.030 (4)
O4	0.062 (4)	0.048 (3)	0.015 (3)	0.009 (3)	0.014 (3)	−0.004 (2)
O5	0.068 (4)	0.102 (5)	0.044 (4)	0.052 (4)	0.047 (4)	0.034 (4)
O6	0.035 (3)	0.050 (3)	0.037 (3)	0.013 (3)	0.024 (3)	0.027 (3)

Geometric parameters (Å, º) top

C1—C2	1.348 (15)	C20—H20B	0.9700
C1—N1	1.364 (13)	C20—H20C	0.9700
C1—H1	0.9300	C20—H20D	0.9700
C2—C3	1.385 (13)	C21—H21A	0.9600
C2—H2	0.9300	C21—H21B	0.9600
C3—C6	1.403 (12)	C21—H21C	0.9600
C3—C4	1.415 (10)	C21'—H21D	0.9600
C4—C5	1.395 (11)	C21'—H21E	0.9600
C4—H4	0.9300	C21'—H21F	0.9600
C5—N1	1.285 (11)	C22—N5	1.453 (8)
C5—H5	0.9300	C22—N4	1.458 (8)
C6—C7	1.216 (12)	C22—C23	1.534 (10)
C7—C8	1.421 (11)	C23—O5	1.181 (10)
C8—C9	1.381 (12)	C23—O6	1.300 (9)
C8—C13	1.406 (10)	C24—O6	1.469 (6)
C9—C10	1.404 (13)	C24—C25'	1.5030
C9—H9	0.9300	C24—C25	1.5208
C10—C11	1.370 (13)	C24—H24A	0.9700
C10—H10	0.9300	C24—H24B	0.9700
C11—C12	1.381 (11)	C24—H24C	0.9700
C11—H11	0.9300	C24—H24D	0.9700
C12—C13	1.391 (10)	C25—H25A	0.9600
C12—C14	1.514 (10)	C25—H25B	0.9600
C13—C15	1.550 (10)	C25—H25C	0.9600
C14—N2	1.468 (10)	C25'—H25D	0.9600
C14—H14A	0.9700	C25'—H25E	0.9600
C14—H14B	0.9700	C25'—H25F	0.9600
C15—N3	1.456 (9)	C26—N4	1.446 (8)
C15—H15A	0.9700	C26—C28	1.517 (9)
C15—H15B	0.9700	C26—H26A	0.9700
C16—O1	1.209 (8)	C26—H26B	0.9700
C16—N2	1.369 (9)	C27—N5	1.441 (9)
C16—N4	1.388 (9)	C27—C29	1.519 (10)
C17—O2	1.204 (8)	C27—H27A	0.9700
C17—N5	1.377 (10)	C27—H27B	0.9700
C17—N3	1.388 (9)	C28—C33	1.406 (10)
C18—N2	1.421 (9)	C28—C29	1.415 (9)
C18—N3	1.440 (8)	C29—C30	1.404 (10)
C18—C22	1.550 (10)	C30—C31	1.390 (11)
C18—C19	1.571 (10)	C30—H30	0.9300
C19—O3	1.201 (10)	C31—C32	1.368 (11)
C19—O4	1.273 (9)	C31—H31	0.9300
C20—O4	1.474 (8)	C32—C33	1.400 (11)
C20—C21	1.5038	C32—H32	0.9300
C20—C21'	1.5111	C33—I1	1.870 (7)
C20—H20A	0.9700

C2—C1—N1	124.7 (9)	H21D—C21'—H21E	109.5
C2—C1—H1	117.6	C20—C21'—H21F	109.5
N1—C1—H1	117.6	H21D—C21'—H21F	109.5
C1—C2—C3	119.9 (9)	H21E—C21'—H21F	109.5
C1—C2—H2	120.0	N5—C22—N4	112.7 (5)
C3—C2—H2	120.0	N5—C22—C23	111.3 (5)
C2—C3—C6	121.1 (8)	N4—C22—C23	110.1 (5)
C2—C3—C4	116.5 (7)	N5—C22—C18	102.9 (5)
C6—C3—C4	122.4 (7)	N4—C22—C18	103.4 (5)
C5—C4—C3	117.4 (8)	C23—C22—C18	116.2 (5)
C5—C4—H4	121.3	O5—C23—O6	125.7 (7)
C3—C4—H4	121.3	O5—C23—C22	123.2 (7)
N1—C5—C4	126.4 (8)	O6—C23—C22	111.0 (6)
N1—C5—H5	116.8	O6—C24—C25'	110.9 (3)
C4—C5—H5	116.8	O6—C24—C25	108.5 (3)
C7—C6—C3	176.1 (8)	C25'—C24—C25	21.1
C6—C7—C8	178.0 (9)	O6—C24—H24A	110.0
C9—C8—C13	120.7 (7)	C25'—C24—H24A	90.0
C9—C8—C7	120.0 (7)	C25—C24—H24A	110.0
C13—C8—C7	119.2 (7)	O6—C24—H24B	110.0
C8—C9—C10	119.8 (7)	C25'—C24—H24B	125.1
C8—C9—H9	120.1	C25—C24—H24B	110.0
C10—C9—H9	120.1	H24A—C24—H24B	108.4
C11—C10—C9	119.0 (8)	O6—C24—H24C	109.3
C11—C10—H10	120.5	C25'—C24—H24C	109.3
C9—C10—H10	120.5	C25—C24—H24C	127.6
C10—C11—C12	122.0 (7)	H24A—C24—H24C	21.3
C10—C11—H11	119.0	H24B—C24—H24C	89.4
C12—C11—H11	119.0	O6—C24—H24D	109.8
C11—C12—C13	119.6 (7)	C25'—C24—H24D	109.3
C11—C12—C14	117.9 (7)	C25—C24—H24D	91.5
C13—C12—C14	122.5 (6)	H24A—C24—H24D	124.8
C12—C13—C8	118.9 (6)	H24B—C24—H24D	20.4
C12—C13—C15	122.1 (6)	H24C—C24—H24D	108.0
C8—C13—C15	118.7 (6)	C24—C25—H25A	109.5
N2—C14—C12	113.8 (6)	C24—C25—H25B	109.5
N2—C14—H14A	108.8	C24—C25—H25C	109.5
C12—C14—H14A	108.8	C24—C25'—H25D	109.5
N2—C14—H14B	108.8	C24—C25'—H25E	109.5
C12—C14—H14B	108.8	H25D—C25'—H25E	109.5
H14A—C14—H14B	107.7	C24—C25'—H25F	109.5
N3—C15—C13	116.2 (5)	H25D—C25'—H25F	109.5
N3—C15—H15A	108.2	H25E—C25'—H25F	109.5
C13—C15—H15A	108.2	N4—C26—C28	115.4 (5)
N3—C15—H15B	108.2	N4—C26—H26A	108.4
C13—C15—H15B	108.2	C28—C26—H26A	108.4
H15A—C15—H15B	107.4	N4—C26—H26B	108.4
O1—C16—N2	127.0 (6)	C28—C26—H26B	108.4
O1—C16—N4	125.5 (6)	H26A—C26—H26B	107.5
N2—C16—N4	107.4 (5)	N5—C27—C29	114.1 (6)
O2—C17—N5	125.5 (7)	N5—C27—H27A	108.7
O2—C17—N3	127.1 (7)	C29—C27—H27A	108.7
N5—C17—N3	107.3 (6)	N5—C27—H27B	108.7
N2—C18—N3	113.9 (5)	C29—C27—H27B	108.7
N2—C18—C22	103.0 (5)	H27A—C27—H27B	107.6
N3—C18—C22	103.4 (5)	C33—C28—C29	117.1 (6)
N2—C18—C19	109.3 (5)	C33—C28—C26	122.0 (6)
N3—C18—C19	113.7 (5)	C29—C28—C26	120.9 (6)
C22—C18—C19	112.9 (5)	C30—C29—C28	121.0 (7)
O3—C19—O4	126.4 (7)	C30—C29—C27	118.3 (6)
O3—C19—C18	120.4 (7)	C28—C29—C27	120.7 (6)
O4—C19—C18	113.2 (6)	C31—C30—C29	119.6 (7)
O4—C20—C21	110.3 (4)	C31—C30—H30	120.2
O4—C20—C21'	109.4 (4)	C29—C30—H30	120.2
C21—C20—C21'	30.2	C32—C31—C30	120.9 (7)
O4—C20—H20A	109.6	C32—C31—H31	119.6
C21—C20—H20A	109.6	C30—C31—H31	119.6
C21'—C20—H20A	132.8	C31—C32—C33	119.8 (7)
O4—C20—H20B	109.6	C31—C32—H32	120.1
C21—C20—H20B	109.6	C33—C32—H32	120.1
C21'—C20—H20B	82.4	C32—C33—C28	121.7 (7)
H20A—C20—H20B	108.1	C32—C33—I1	116.3 (6)
O4—C20—H20C	110.4	C28—C33—I1	122.1 (5)
C21—C20—H20C	82.1	C5—N1—C1	115.0 (8)
C21'—C20—H20C	109.9	C16—N2—C18	113.9 (6)
H20A—C20—H20C	29.8	C16—N2—C14	123.8 (6)
H20B—C20—H20C	130.5	C18—N2—C14	122.3 (6)
O4—C20—H20D	109.8	C17—N3—C18	111.5 (5)
C21—C20—H20D	131.3	C17—N3—C15	121.4 (6)
C21'—C20—H20D	109.1	C18—N3—C15	120.9 (5)
H20A—C20—H20D	81.3	C16—N4—C26	122.0 (5)
H20B—C20—H20D	29.1	C16—N4—C22	110.5 (5)
H20C—C20—H20D	108.3	C26—N4—C22	121.8 (5)
C20—C21—H21A	109.5	C17—N5—C27	126.2 (6)
C20—C21—H21B	109.5	C17—N5—C22	112.4 (6)
C20—C21—H21C	109.5	C27—N5—C22	121.1 (6)
C20—C21'—H21D	109.5	C19—O4—C20	113.7 (6)
C20—C21'—H21E	109.5	C23—O6—C24	115.2 (5)

N1—C1—C2—C3	0.9 (15)	C31—C32—C33—I1	−179.2 (6)
C1—C2—C3—C6	−179.6 (8)	C29—C28—C33—C32	1.4 (10)
C1—C2—C3—C4	−2.3 (13)	C26—C28—C33—C32	−178.1 (7)
C2—C3—C4—C5	1.7 (11)	C29—C28—C33—I1	−179.9 (5)
C6—C3—C4—C5	178.9 (7)	C26—C28—C33—I1	0.6 (10)
C3—C4—C5—N1	0.4 (13)	C4—C5—N1—C1	−1.8 (13)
C2—C3—C6—C7	−1 (13)	C2—C1—N1—C5	1.1 (14)
C4—C3—C6—C7	−179 (100)	O1—C16—N2—C18	−178.2 (6)
C3—C6—C7—C8	−52 (32)	N4—C16—N2—C18	4.9 (7)
C6—C7—C8—C9	−73 (24)	O1—C16—N2—C14	0.7 (10)
C6—C7—C8—C13	105 (24)	N4—C16—N2—C14	−176.3 (6)
C13—C8—C9—C10	0.4 (12)	N3—C18—N2—C16	115.0 (6)
C7—C8—C9—C10	178.6 (8)	C22—C18—N2—C16	3.8 (7)
C8—C9—C10—C11	−2.1 (13)	C19—C18—N2—C16	−116.5 (6)
C9—C10—C11—C12	3.3 (13)	N3—C18—N2—C14	−63.9 (8)
C10—C11—C12—C13	−2.7 (12)	C22—C18—N2—C14	−175.1 (6)
C10—C11—C12—C14	175.6 (8)	C19—C18—N2—C14	64.6 (8)
C11—C12—C13—C8	0.9 (10)	C12—C14—N2—C16	−101.3 (8)
C14—C12—C13—C8	−177.3 (7)	C12—C14—N2—C18	77.5 (9)
C11—C12—C13—C15	174.7 (7)	O2—C17—N3—C18	168.8 (6)
C14—C12—C13—C15	−3.5 (10)	N5—C17—N3—C18	−14.7 (7)
C9—C8—C13—C12	0.2 (10)	O2—C17—N3—C15	16.2 (10)
C7—C8—C13—C12	−178.0 (7)	N5—C17—N3—C15	−167.2 (5)
C9—C8—C13—C15	−173.9 (7)	N2—C18—N3—C17	−94.5 (7)
C7—C8—C13—C15	7.9 (10)	C22—C18—N3—C17	16.5 (7)
C11—C12—C14—N2	129.3 (7)	C19—C18—N3—C17	139.3 (6)
C13—C12—C14—N2	−52.4 (10)	N2—C18—N3—C15	58.2 (8)
C12—C13—C15—N3	57.1 (9)	C22—C18—N3—C15	169.2 (5)
C8—C13—C15—N3	−129.1 (7)	C19—C18—N3—C15	−68.0 (8)
N2—C18—C19—O3	25.6 (10)	C13—C15—N3—C17	79.0 (7)
N3—C18—C19—O3	154.2 (8)	C13—C15—N3—C18	−71.0 (8)
C22—C18—C19—O3	−88.4 (9)	O1—C16—N4—C26	16.9 (9)
N2—C18—C19—O4	−153.2 (6)	N2—C16—N4—C26	−166.1 (5)
N3—C18—C19—O4	−24.6 (9)	O1—C16—N4—C22	170.8 (6)
C22—C18—C19—O4	92.8 (7)	N2—C16—N4—C22	−12.2 (7)
N2—C18—C22—N5	107.1 (5)	C28—C26—N4—C16	75.6 (7)
N3—C18—C22—N5	−11.8 (6)	C28—C26—N4—C22	−75.4 (8)
C19—C18—C22—N5	−135.1 (6)	N5—C22—N4—C16	−96.4 (6)
N2—C18—C22—N4	−10.3 (6)	C23—C22—N4—C16	138.8 (6)
N3—C18—C22—N4	−129.2 (5)	C18—C22—N4—C16	14.0 (6)
C19—C18—C22—N4	107.5 (6)	N5—C22—N4—C26	57.6 (8)
N2—C18—C22—C23	−131.1 (6)	C23—C22—N4—C26	−67.2 (7)
N3—C18—C22—C23	110.1 (6)	C18—C22—N4—C26	168.0 (5)
C19—C18—C22—C23	−13.3 (8)	O2—C17—N5—C27	−3.3 (11)
N5—C22—C23—O5	−146.3 (8)	N3—C17—N5—C27	−179.9 (6)
N4—C22—C23—O5	−20.7 (10)	O2—C17—N5—C22	−177.3 (6)
C18—C22—C23—O5	96.4 (9)	N3—C17—N5—C22	6.1 (7)
N5—C22—C23—O6	36.8 (8)	C29—C27—N5—C17	−94.3 (8)
N4—C22—C23—O6	162.4 (6)	C29—C27—N5—C22	79.2 (8)
C18—C22—C23—O6	−80.5 (7)	N4—C22—N5—C17	114.5 (6)
N4—C26—C28—C33	−122.6 (7)	C23—C22—N5—C17	−121.3 (6)
N4—C26—C28—C29	57.9 (9)	C18—C22—N5—C17	3.8 (7)
C33—C28—C29—C30	−1.4 (10)	N4—C22—N5—C27	−59.8 (8)
C26—C28—C29—C30	178.1 (6)	C23—C22—N5—C27	64.4 (7)
C33—C28—C29—C27	−179.0 (6)	C18—C22—N5—C27	−170.5 (5)
C26—C28—C29—C27	0.5 (10)	O3—C19—O4—C20	4.2 (13)
N5—C27—C29—C30	122.6 (7)	C18—C19—O4—C20	−177.2 (7)
N5—C27—C29—C28	−59.8 (9)	C21—C20—O4—C19	162.9 (5)
C28—C29—C30—C31	0.5 (11)	C21'—C20—O4—C19	−165.0 (5)
C27—C29—C30—C31	178.1 (7)	O5—C23—O6—C24	−3.0 (12)
C29—C30—C31—C32	0.6 (12)	C22—C23—O6—C24	173.8 (6)
C30—C31—C32—C33	−0.7 (12)	C25'—C24—O6—C23	160.6 (5)
C31—C32—C33—C28	−0.3 (11)	C25—C24—O6—C23	−177.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26A···I1	0.97	2.62	3.217 (7)	120
C14—H14A···N1ⁱ	0.97	2.55	3.480 (12)	160
C25—H25B···O1ⁱⁱ	0.96	2.49	3.403 (8)	159
C32—H32···O5ⁱⁱⁱ	0.93	2.55	3.153 (10)	123

Symmetry codes: (i) −x+1, y+1, −z+3/2; (ii) x, −y+1, z+1/2; (iii) x, −y+1, z−1/2.

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