Diethyl 7,12-dihydro-8-iodo-6,13-dioxo-cis-7H,11H-2,4-dioxa-5a,6a,12a,13a-tetra­azabenz[f]cyclo­octa­[cd]azulene-13b,13c-dicarboxyl­ate

The title compound, C₂₁H₂₃IN₄O₈, is a glycoluril derivative with five fused rings. An iodo­benzene ring is fused to a seven-membered ring which binds two of the N atoms from separate rings of the glycoluril system. The other N atoms are linked via methyl­ene groups to form an eight-membered ring with two ether O atoms separated by an additional methyl­ene group. The crystal structure is stabilized by inversion-related C—H...π inter­actions together with C—H...O non-classical hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.008 Å
• Disorder in main residue
• R factor = 0.048
• wR factor = 0.125
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT410_ALERT_2_A Short Intra H...H Contact  H19A   ..  H21C    ..       1.77 Ang.

Author Response: The bond should be omitted as C21 is disordered.

Alert level B
PLAT410_ALERT_2_B Short Intra H...H Contact  H20B   ..  H21C    ..       1.80 Ang.

Author Response: The bond should be omitted as C21 is disordered.

Alert level C
ABSTM02_ALERT_3_C  The ratio of Tmax/Tmin expected RT(exp) is > 1.10
            Absorption corrections should be applied.
            Tmin and Tmax expected:      0.702     0.797
            RT(exp) =      1.136
PLAT057_ALERT_3_C Correction for Absorption Required   RT(exp) ...       1.13
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.46
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.63 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.22 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C19
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C20
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C21
PLAT301_ALERT_3_C Main Residue  Disorder .........................       6.00 Perc.
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........         O7
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........         O8
PLAT431_ALERT_2_C Short Inter HL..A Contact  I1     ..  O3      ..       3.26 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8B    ..  CG1     ..       2.91 Ang.

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  13 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
  10 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

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 7,12-dihydro-8-iodo-6,13-dioxo-cis-1H,3H,5H,4H,11H-2,4- dioxa-5a,6a,12a,13a-tetraazabenz[f]cycloocta[cd]azulene-13b,13c-dicarboxylate

Crystal data

C21H23IN4O8	Z = 2
Mr = 570.33	F(000) = 572
Triclinic, P1	Dx = 1.727 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2832 (12) Å	Cell parameters from 4288 reflections
b = 9.7080 (14) Å	θ = 2.3–25.8°
c = 14.872 (2) Å	µ = 1.51 mm^−1
α = 99.300 (2)°	T = 292 K
β = 97.076 (2)°	Irregular, colorless
γ = 108.921 (2)°	0.30 × 0.20 × 0.15 mm
V = 1096.5 (3) Å^3

Data collection

Bruker SMART Apex CCD area-detector diffractometer	3405 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 25.0°, θmin = 2.3°
ω scans	h = −9→9
6102 measured reflections	k = −11→10
3785 independent reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0722P)^2 + 1.3642P] where P = (Fo^2 + 2Fc^2)/3
3785 reflections	(Δ/σ)max < 0.001
313 parameters	Δρmax = 1.50 e Å^−3
0 restraints	Δρmin = −0.61 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.9255 (6)	1.1198 (5)	0.5851 (3)	0.0329 (10)
C2	0.9327 (6)	1.2269 (5)	0.5323 (3)	0.0364 (10)
C3	1.0886 (7)	1.3363 (6)	0.5309 (4)	0.0439 (12)
H3	1.0903	1.4062	0.4946	0.053*
C4	1.2398 (7)	1.3421 (6)	0.5825 (4)	0.0491 (13)
H4	1.3441	1.4160	0.5817	0.059*
C5	1.2373 (7)	1.2381 (6)	0.6358 (4)	0.0443 (12)
H5	1.3406	1.2424	0.6708	0.053*
C6	1.0832 (6)	1.1270 (5)	0.6381 (3)	0.0354 (10)
C7	1.0870 (6)	1.0138 (6)	0.6954 (3)	0.0382 (11)
H7A	1.0504	0.9166	0.6541	0.046*
H7B	1.2061	1.0371	0.7258	0.046*
C8	0.7596 (6)	0.9977 (5)	0.5850 (3)	0.0334 (10)
H8A	0.6665	1.0093	0.5441	0.040*
H8B	0.7697	0.9030	0.5596	0.040*
C9	0.6538 (6)	1.0998 (6)	0.7194 (3)	0.0387 (11)
C10	1.0382 (7)	1.0799 (5)	0.8557 (3)	0.0404 (12)
C11	0.7938 (6)	0.9315 (5)	0.7415 (3)	0.0330 (10)
C12	0.7375 (7)	0.7608 (5)	0.7075 (3)	0.0368 (11)
C13	0.8265 (9)	0.5516 (6)	0.7095 (4)	0.0588 (16)
H13A	0.7276	0.5008	0.7355	0.071*
H13B	0.7991	0.5148	0.6428	0.071*
C14	0.9793 (11)	0.5238 (9)	0.7489 (6)	0.086 (2)
H14A	1.0790	0.5831	0.7281	0.129*
H14B	0.9626	0.4202	0.7294	0.129*
H14C	0.9975	0.5499	0.8154	0.129*
C15	0.7325 (7)	0.9814 (6)	0.8348 (3)	0.0399 (11)
C16	0.6084 (8)	0.8561 (7)	0.8714 (4)	0.0541 (15)
C17	0.5713 (10)	0.6279 (7)	0.9197 (4)	0.0665 (18)
H17A	0.6480	0.5810	0.9454	0.080*
H17B	0.5209	0.6651	0.9695	0.080*
C18	0.4333 (10)	0.5173 (8)	0.8489 (5)	0.0731 (19)
H18A	0.3464	0.5583	0.8308	0.110*
H18B	0.3818	0.4307	0.8731	0.110*
H18C	0.4806	0.4897	0.7959	0.110*
C19	0.9066 (11)	1.1557 (7)	0.9835 (4)	0.071 (2)
H19A	0.7910	1.1285	0.9984	0.085*
H19B	0.9807	1.1385	1.0329	0.085*
C20	0.6223 (11)	1.1929 (8)	0.8768 (5)	0.077 (2)
H20A	0.5089	1.1948	0.8528	0.092*
H20B	0.6104	1.1514	0.9318	0.092*
C21	0.8154 (13)	1.2629 (8)	0.9393 (6)	0.0453 (18)	0.642 (9)
H21A	0.7397	1.2022	0.9738	0.054*	0.642 (9)
H21B	0.8182	1.1938	0.8851	0.054*	0.642 (9)
C21'	0.825 (2)	1.3504 (15)	0.9908 (10)	0.0453 (18)	0.358 (9)
H21C	0.7499	1.2961	1.0283	0.054*	0.358 (9)
H21D	0.8697	1.4548	1.0218	0.054*	0.358 (9)
I1	0.71161 (4)	1.23344 (4)	0.44998 (2)	0.04657 (16)
N1	0.9784 (5)	1.0046 (4)	0.7658 (3)	0.0365 (9)
N2	0.7109 (5)	0.9924 (4)	0.6768 (2)	0.0321 (8)
N3	0.8967 (6)	1.0523 (5)	0.9000 (3)	0.0405 (10)
N4	0.6529 (7)	1.0850 (5)	0.8098 (3)	0.0503 (11)
O1	0.6099 (6)	1.1877 (5)	0.6836 (3)	0.0578 (10)
O2	1.1869 (5)	1.1523 (5)	0.8913 (3)	0.0620 (11)
O3	0.5961 (5)	0.6870 (4)	0.6651 (3)	0.0536 (10)
O4	0.8645 (5)	0.7126 (4)	0.7317 (3)	0.0464 (9)
O5	0.4749 (8)	0.8608 (6)	0.8900 (5)	0.0933 (18)
O6	0.6728 (5)	0.7532 (4)	0.8832 (2)	0.0529 (10)
O7	0.9621 (13)	1.3006 (9)	0.9874 (6)	0.059 (2)	0.50
O8	0.7265 (12)	1.3358 (9)	0.9067 (6)	0.061 (2)	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.037 (3)	0.028 (2)	0.027 (2)	0.0081 (19)	0.0038 (18)	−0.0022 (17)
C2	0.035 (3)	0.038 (3)	0.031 (2)	0.010 (2)	0.0032 (19)	0.0026 (19)
C3	0.044 (3)	0.038 (3)	0.044 (3)	0.008 (2)	0.010 (2)	0.008 (2)
C4	0.040 (3)	0.043 (3)	0.053 (3)	0.001 (2)	0.012 (2)	0.006 (2)
C5	0.036 (3)	0.049 (3)	0.040 (3)	0.012 (2)	0.003 (2)	0.000 (2)
C6	0.031 (2)	0.041 (3)	0.031 (2)	0.012 (2)	0.0060 (19)	−0.0011 (19)
C7	0.035 (3)	0.041 (3)	0.037 (2)	0.014 (2)	0.005 (2)	0.002 (2)
C8	0.033 (2)	0.034 (2)	0.027 (2)	0.006 (2)	0.0007 (18)	0.0039 (18)
C9	0.033 (3)	0.038 (3)	0.043 (3)	0.013 (2)	0.006 (2)	0.005 (2)
C10	0.055 (3)	0.032 (3)	0.029 (2)	0.011 (2)	0.000 (2)	0.0056 (19)
C11	0.039 (3)	0.030 (2)	0.029 (2)	0.013 (2)	0.0058 (19)	0.0023 (18)
C12	0.049 (3)	0.034 (3)	0.024 (2)	0.011 (2)	0.006 (2)	0.0040 (19)
C13	0.085 (5)	0.037 (3)	0.061 (4)	0.026 (3)	0.024 (3)	0.009 (3)
C14	0.098 (6)	0.064 (5)	0.111 (6)	0.052 (4)	0.010 (5)	0.017 (4)
C15	0.046 (3)	0.047 (3)	0.028 (2)	0.019 (2)	0.010 (2)	0.002 (2)
C16	0.055 (4)	0.055 (4)	0.042 (3)	0.009 (3)	0.016 (3)	−0.002 (3)
C17	0.086 (5)	0.061 (4)	0.040 (3)	0.005 (3)	0.011 (3)	0.018 (3)
C18	0.082 (5)	0.066 (4)	0.059 (4)	0.007 (4)	0.012 (3)	0.019 (3)
C19	0.108 (6)	0.048 (4)	0.037 (3)	0.001 (3)	0.025 (3)	−0.003 (3)
C20	0.105 (6)	0.058 (4)	0.075 (5)	0.031 (4)	0.053 (4)	0.002 (3)
C21	0.065 (5)	0.026 (3)	0.041 (4)	0.013 (3)	0.017 (4)	−0.003 (3)
C21'	0.065 (5)	0.026 (3)	0.041 (4)	0.013 (3)	0.017 (4)	−0.003 (3)
I1	0.0457 (2)	0.0459 (2)	0.0452 (2)	0.01250 (16)	0.00297 (15)	0.01365 (15)
N1	0.037 (2)	0.037 (2)	0.030 (2)	0.0117 (18)	0.0003 (16)	−0.0008 (16)
N2	0.033 (2)	0.032 (2)	0.0285 (19)	0.0100 (17)	0.0045 (15)	0.0042 (15)
N3	0.051 (3)	0.036 (2)	0.0263 (19)	0.0103 (19)	0.0023 (18)	−0.0021 (16)
N4	0.062 (3)	0.057 (3)	0.041 (2)	0.037 (2)	0.013 (2)	0.002 (2)
O1	0.063 (3)	0.054 (2)	0.074 (3)	0.038 (2)	0.021 (2)	0.023 (2)
O2	0.050 (2)	0.070 (3)	0.037 (2)	−0.006 (2)	−0.0062 (18)	0.0010 (19)
O3	0.058 (3)	0.037 (2)	0.050 (2)	0.0065 (18)	−0.0117 (19)	0.0049 (17)
O4	0.054 (2)	0.0326 (18)	0.053 (2)	0.0182 (17)	0.0062 (17)	0.0072 (16)
O5	0.079 (4)	0.075 (3)	0.140 (5)	0.027 (3)	0.064 (4)	0.029 (3)
O6	0.063 (3)	0.054 (2)	0.0361 (19)	0.012 (2)	0.0068 (17)	0.0159 (17)
O7	0.077 (6)	0.045 (5)	0.063 (5)	0.027 (4)	0.023 (5)	0.009 (4)
O8	0.071 (6)	0.051 (5)	0.058 (5)	0.022 (4)	0.014 (4)	0.005 (4)

Geometric parameters (Å, º)

C1—C2	1.391 (7)	C13—H13B	0.9700
C1—C6	1.414 (7)	C14—H14A	0.9600
C1—C8	1.495 (6)	C14—H14B	0.9600
C2—C3	1.387 (7)	C14—H14C	0.9600
C2—I1	2.099 (5)	C15—N4	1.441 (7)
C3—C4	1.365 (8)	C15—N3	1.455 (7)
C3—H3	0.9300	C15—C16	1.540 (8)
C4—C5	1.377 (8)	C16—O5	1.185 (8)
C4—H4	0.9300	C16—O6	1.301 (7)
C5—C6	1.387 (7)	C17—C18	1.453 (10)
C5—H5	0.9300	C17—O6	1.464 (7)
C6—C7	1.502 (7)	C17—H17A	0.9700
C7—N1	1.457 (6)	C17—H17B	0.9700
C7—H7A	0.9700	C18—H18A	0.9600
C7—H7B	0.9700	C18—H18B	0.9600
C8—N2	1.474 (6)	C18—H18C	0.9600
C8—H8A	0.9700	C19—O7	1.319 (10)
C8—H8B	0.9700	C19—N3	1.441 (7)
C9—O1	1.202 (6)	C19—H19A	0.9700
C9—N2	1.375 (6)	C19—H19B	0.9700
C9—N4	1.376 (7)	C20—O8	1.341 (11)
C10—O2	1.204 (6)	C20—N4	1.432 (7)
C10—N1	1.362 (6)	C20—H20A	0.9700
C10—N3	1.388 (7)	C20—H20B	0.9700
C11—N2	1.425 (6)	C21—O7	1.239 (13)
C11—N1	1.432 (6)	C21—O8	1.280 (12)
C11—C12	1.545 (6)	C21—H21A	0.9700
C11—C15	1.592 (6)	C21—H21B	0.9700
C12—O3	1.188 (6)	C21'—O8	1.365 (18)
C12—O4	1.318 (6)	C21'—O7	1.377 (18)
C13—C14	1.452 (10)	C21'—H21C	0.9700
C13—O4	1.463 (6)	C21'—H21D	0.9700
C13—H13A	0.9700
C2—C1—C6	117.7 (4)	N3—C15—C11	102.1 (4)
C2—C1—C8	122.2 (4)	C16—C15—C11	116.3 (4)
C6—C1—C8	120.1 (4)	O5—C16—O6	125.9 (6)
C3—C2—C1	121.4 (5)	O5—C16—C15	122.1 (6)
C3—C2—I1	115.8 (4)	O6—C16—C15	111.9 (5)
C1—C2—I1	122.8 (4)	C18—C17—O6	112.3 (5)
C4—C3—C2	120.3 (5)	C18—C17—H17A	109.2
C4—C3—H3	119.8	O6—C17—H17A	109.2
C2—C3—H3	119.8	C18—C17—H17B	109.2
C3—C4—C5	119.8 (5)	O6—C17—H17B	109.2
C3—C4—H4	120.1	H17A—C17—H17B	107.9
C5—C4—H4	120.1	C17—C18—H18A	109.5
C4—C5—C6	121.1 (5)	C17—C18—H18B	109.5
C4—C5—H5	119.5	H18A—C18—H18B	109.5
C6—C5—H5	119.5	C17—C18—H18C	109.5
C5—C6—C1	119.8 (5)	H18A—C18—H18C	109.5
C5—C6—C7	119.3 (4)	H18B—C18—H18C	109.5
C1—C6—C7	120.9 (4)	O7—C19—N3	120.8 (6)
N1—C7—C6	115.2 (4)	O7—C19—H19A	107.1
N1—C7—H7A	108.5	N3—C19—H19A	107.1
C6—C7—H7A	108.5	O7—C19—H19B	107.1
N1—C7—H7B	108.5	N3—C19—H19B	107.1
C6—C7—H7B	108.5	H19A—C19—H19B	106.8
H7A—C7—H7B	107.5	O8—C20—N4	125.3 (7)
N2—C8—C1	114.9 (4)	O8—C20—H20A	106.0
N2—C8—H8A	108.5	N4—C20—H20A	106.0
C1—C8—H8A	108.5	O8—C20—H20B	106.0
N2—C8—H8B	108.5	N4—C20—H20B	106.0
C1—C8—H8B	108.5	H20A—C20—H20B	106.3
H8A—C8—H8B	107.5	O7—C21—O8	133.4 (9)
O1—C9—N2	126.3 (5)	O7—C21—H21A	103.9
O1—C9—N4	126.7 (5)	O8—C21—H21A	103.9
N2—C9—N4	107.0 (4)	O7—C21—H21B	103.9
O2—C10—N1	126.7 (5)	O8—C21—H21B	103.9
O2—C10—N3	126.1 (4)	H21A—C21—H21B	105.4
N1—C10—N3	107.2 (4)	O8—C21'—O7	115.1 (11)
N2—C11—N1	113.8 (4)	O8—C21'—H21C	108.5
N2—C11—C12	110.2 (4)	O7—C21'—H21C	108.5
N1—C11—C12	113.2 (4)	O8—C21'—H21D	108.5
N2—C11—C15	102.6 (4)	O7—C21'—H21D	108.5
N1—C11—C15	102.2 (4)	H21C—C21'—H21D	107.5
C12—C11—C15	114.2 (4)	C10—N1—C11	114.7 (4)
O3—C12—O4	126.4 (5)	C10—N1—C7	123.5 (4)
O3—C12—C11	122.2 (5)	C11—N1—C7	121.3 (4)
O4—C12—C11	111.4 (4)	C9—N2—C11	112.6 (4)
C14—C13—O4	107.9 (6)	C9—N2—C8	120.1 (4)
C14—C13—H13A	110.1	C11—N2—C8	120.7 (4)
O4—C13—H13A	110.1	C10—N3—C19	118.8 (5)
C14—C13—H13B	110.1	C10—N3—C15	112.2 (4)
O4—C13—H13B	110.1	C19—N3—C15	119.5 (5)
H13A—C13—H13B	108.4	C9—N4—C20	121.2 (5)
C13—C14—H14A	109.5	C9—N4—C15	113.4 (4)
C13—C14—H14B	109.5	C20—N4—C15	123.1 (5)
H14A—C14—H14B	109.5	C12—O4—C13	117.5 (4)
C13—C14—H14C	109.5	C16—O6—C17	118.4 (5)
H14A—C14—H14C	109.5	C21—O7—C19	79.7 (8)
H14B—C14—H14C	109.5	C21—O7—C21'	45.7 (8)
N4—C15—N3	113.5 (4)	C19—O7—C21'	109.2 (10)
N4—C15—C16	112.2 (5)	C21—O8—C20	76.0 (7)
N3—C15—C16	110.4 (4)	C21—O8—C21'	45.4 (7)
N4—C15—C11	101.8 (4)	C20—O8—C21'	108.5 (9)
C6—C1—C2—C3	0.5 (7)	O1—C9—N2—C8	13.5 (8)
C8—C1—C2—C3	−177.8 (4)	N4—C9—N2—C8	−167.8 (4)
C6—C1—C2—I1	−179.8 (3)	N1—C11—N2—C9	−93.1 (5)
C8—C1—C2—I1	1.9 (6)	C12—C11—N2—C9	138.6 (4)
C1—C2—C3—C4	−0.6 (8)	C15—C11—N2—C9	16.5 (5)
I1—C2—C3—C4	179.7 (4)	N1—C11—N2—C8	58.4 (5)
C2—C3—C4—C5	0.4 (8)	C12—C11—N2—C8	−70.0 (5)
C3—C4—C5—C6	−0.1 (8)	C15—C11—N2—C8	168.0 (4)
C4—C5—C6—C1	−0.1 (7)	C1—C8—N2—C9	71.6 (5)
C4—C5—C6—C7	178.6 (5)	C1—C8—N2—C11	−77.7 (5)
C2—C1—C6—C5	−0.1 (7)	O2—C10—N3—C19	24.8 (8)
C8—C1—C6—C5	178.2 (4)	N1—C10—N3—C19	−157.9 (5)
C2—C1—C6—C7	−178.8 (4)	O2—C10—N3—C15	170.8 (5)
C8—C1—C6—C7	−0.5 (6)	N1—C10—N3—C15	−11.8 (6)
C5—C6—C7—N1	122.6 (5)	O7—C19—N3—C10	47.5 (11)
C1—C6—C7—N1	−58.7 (6)	O7—C19—N3—C15	−96.1 (9)
C2—C1—C8—N2	−122.1 (5)	N4—C15—N3—C10	−95.3 (5)
C6—C1—C8—N2	59.6 (6)	C16—C15—N3—C10	137.7 (4)
N2—C11—C12—O3	−33.7 (6)	C11—C15—N3—C10	13.4 (5)
N1—C11—C12—O3	−162.4 (4)	N4—C15—N3—C19	50.5 (6)
C15—C11—C12—O3	81.2 (6)	C16—C15—N3—C19	−76.5 (6)
N2—C11—C12—O4	146.4 (4)	C11—C15—N3—C19	159.2 (4)
N1—C11—C12—O4	17.7 (5)	O1—C9—N4—C20	−9.9 (9)
C15—C11—C12—O4	−98.7 (5)	N2—C9—N4—C20	171.5 (6)
N2—C11—C15—N4	−10.4 (5)	O1—C9—N4—C15	−173.0 (5)
N1—C11—C15—N4	107.8 (4)	N2—C9—N4—C15	8.3 (6)
C12—C11—C15—N4	−129.6 (4)	O8—C20—N4—C9	−64.8 (11)
N2—C11—C15—N3	−127.9 (4)	O8—C20—N4—C15	96.7 (10)
N1—C11—C15—N3	−9.7 (5)	N3—C15—N4—C9	110.5 (5)
C12—C11—C15—N3	112.9 (4)	C16—C15—N4—C9	−123.4 (5)
N2—C11—C15—C16	111.8 (5)	C11—C15—N4—C9	1.6 (6)
N1—C11—C15—C16	−130.0 (5)	N3—C15—N4—C20	−52.3 (7)
C12—C11—C15—C16	−7.4 (6)	C16—C15—N4—C20	73.8 (7)
N4—C15—C16—O5	−11.3 (8)	C11—C15—N4—C20	−161.2 (6)
N3—C15—C16—O5	116.5 (7)	O3—C12—O4—C13	−3.9 (7)
C11—C15—C16—O5	−127.8 (6)	C11—C12—O4—C13	176.0 (4)
N4—C15—C16—O6	172.2 (4)	C14—C13—O4—C12	−175.4 (6)
N3—C15—C16—O6	−60.0 (6)	O5—C16—O6—C17	2.3 (9)
C11—C15—C16—O6	55.7 (6)	C15—C16—O6—C17	178.7 (4)
O2—C10—N1—C11	−178.1 (5)	C18—C17—O6—C16	79.0 (8)
N3—C10—N1—C11	4.5 (6)	O8—C21—O7—C19	174.4 (11)
O2—C10—N1—C7	−6.7 (8)	O8—C21—O7—C21'	44.4 (13)
N3—C10—N1—C7	176.0 (4)	N3—C19—O7—C21	74.5 (9)
N2—C11—N1—C10	113.5 (4)	N3—C19—O7—C21'	109.9 (10)
C12—C11—N1—C10	−119.7 (4)	O8—C21'—O7—C21	−31.8 (10)
C15—C11—N1—C10	3.6 (5)	O8—C21'—O7—C19	−84.7 (13)
N2—C11—N1—C7	−58.2 (6)	O7—C21—O8—C20	179.9 (11)
C12—C11—N1—C7	68.7 (5)	O7—C21—O8—C21'	−45.2 (13)
C15—C11—N1—C7	−168.0 (4)	N4—C20—O8—C21	−68.2 (10)
C6—C7—N1—C10	−94.5 (5)	N4—C20—O8—C21'	−100.3 (11)
C6—C7—N1—C11	76.4 (6)	O7—C21'—O8—C21	30.8 (9)
O1—C9—N2—C11	165.1 (5)	O7—C21'—O8—C20	77.3 (13)
N4—C9—N2—C11	−16.2 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···I1	0.97	2.72	3.363 (5)	124
C5—H5···O1^i	0.93	2.45	3.290 (7)	151
C8—H8B···Cg1^ii	0.97	2.91	3.716 (5)	141

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