Diethyl 3,3′-(cis-[4a]-cisoid-[4a,4b]-cis-[4b]-9,11-dimethyl-2,4,6,8-tetra­oxoperhydro­cyclo­buta[1,2-d:3,4-d]dipyrimidine-1,5-di­yl)dipropionate

In the title compound, C₂₀H₂₈N₄O₈, the two methyl groups attached to the cyclo­butane ring are cis oriented. The crystal structure is stabilized by inter­molecular N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.046
• wR factor = 0.118
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found





Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.93 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.64 Ratio
PLAT301_ALERT_3_C Main Residue  Disorder .........................       6.00 Perc.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 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
   1 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Diethyl 3,3'-(cis-[4a]-cisoid-[4a,4 b]-cis-[4 b]-9,11-dimethyl-2,4,6,8- tetraoxoperhydrocyclobuta[1,2 - d:3,4 - d]dipyrimidine-1,5-diyl)dipropionate

Crystal data

C20H28N4O8	F(000) = 960
Mr = 452.46	Dx = 1.331 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.918 (6) Å	Cell parameters from 952 reflections
b = 12.090 (6) Å	θ = 2.4–25.1°
c = 15.488 (8) Å	µ = 0.10 mm^−1
β = 110.993 (8)°	T = 293 K
V = 2258 (2) Å^3	Block, colorless
Z = 4	0.38 × 0.36 × 0.34 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4613 independent reflections
Radiation source: fine-focus sealed tube	2990 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 26.4°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→15
Tmin = 0.903, Tmax = 1.000	k = −12→15
12464 measured reflections	l = −19→13

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0517P)^2 + 0.5195P] where P = (Fo^2 + 2Fc^2)/3
4613 reflections	(Δ/σ)max < 0.001
304 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Experimental. ¹H NMR (300 MHz, [D₆]DMSO): deta=1.18 (t, J=7.0 Hz, 6H), 1.44 (s, 6H), 2.64 (m, 4H), 3.23 (m, 2H), 3.72 (s, 2H), 3.81 (m, 2H), 4.07 (q, J=7.0 Hz, 4H), 10.34 (s, 2H); ¹³C NMR (300 MHz, [D₆]DMSO): deta=14.05, 23.10, 32.49, 40.35, 48.13, 60.06, 61.69, 150.96, 170.77, 171.24. TOFMS (CI) calcd for (M⁺) C₂₀H₂₉N₄O₈: 453.1985, found: 453.1989.

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)
N1	0.14325 (12)	0.28163 (13)	0.11190 (10)	0.0336 (4)
N2	0.07294 (12)	0.45131 (13)	0.13842 (11)	0.0377 (4)
H2A	0.0629	0.5198	0.1225	0.045*
N3	−0.19393 (12)	0.27695 (13)	0.15140 (10)	0.0320 (4)
N4	−0.18893 (12)	0.35457 (14)	0.01436 (11)	0.0376 (4)
H4A	−0.2145	0.4051	−0.0269	0.045*
O1	0.20700 (12)	0.44207 (13)	0.07575 (11)	0.0562 (4)
O2	−0.03526 (12)	0.47539 (12)	0.22356 (10)	0.0516 (4)
O3	−0.32706 (11)	0.39572 (13)	0.06667 (10)	0.0499 (4)
O4	−0.06555 (11)	0.31140 (12)	−0.05270 (9)	0.0451 (4)
O5	0.42613 (13)	0.16069 (13)	0.28547 (11)	0.0559 (4)
O6	0.28324 (13)	0.05219 (15)	0.20681 (12)	0.0713 (5)
O7	−0.44422 (12)	0.04475 (13)	0.14332 (12)	0.0613 (5)
O8	−0.25979 (13)	0.03946 (14)	0.18792 (13)	0.0707 (5)
C1	0.14510 (15)	0.39243 (17)	0.10654 (13)	0.0365 (5)
C2	0.01603 (14)	0.41271 (17)	0.19230 (13)	0.0350 (4)
C3	0.02554 (14)	0.28993 (15)	0.21236 (12)	0.0308 (4)
C4	0.06520 (14)	0.22552 (15)	0.14415 (12)	0.0318 (4)
H4	0.0980	0.1554	0.1729	0.038*
C5	−0.05881 (14)	0.20421 (15)	0.07982 (12)	0.0310 (4)
C6	−0.08754 (14)	0.22644 (15)	0.16642 (12)	0.0299 (4)
H6	−0.0836	0.1564	0.1993	0.036*
C7	−0.24164 (15)	0.34482 (16)	0.07926 (13)	0.0342 (4)
C8	−0.10286 (14)	0.29448 (16)	0.00837 (12)	0.0323 (4)
C9	0.08799 (17)	0.2723 (2)	0.31571 (13)	0.0481 (6)
H9A	0.1596	0.3067	0.3335	0.072*
H9B	0.0969	0.1945	0.3286	0.072*
H9C	0.0467	0.3046	0.3500	0.072*
C10	−0.08983 (18)	0.09129 (18)	0.03396 (16)	0.0505 (6)
H10A	−0.1689	0.0824	0.0122	0.076*
H10B	−0.0554	0.0343	0.0781	0.076*
H10C	−0.0648	0.0861	−0.0172	0.076*
C11	0.20756 (16)	0.21850 (18)	0.06763 (13)	0.0415 (5)
H11A	0.2038	0.2556	0.0111	0.050*
H11B	0.1748	0.1457	0.0512	0.050*
C12	0.32815 (16)	0.20599 (19)	0.12987 (15)	0.0456 (5)
H12A	0.3700	0.1765	0.0941	0.055*
H12B	0.3583	0.2782	0.1529	0.055*
C13	0.34127 (16)	0.13082 (18)	0.21013 (15)	0.0442 (5)
C14	0.4494 (2)	0.0907 (2)	0.36797 (17)	0.0630 (7)	0.535 (5)
H14A	0.5288	0.0864	0.4011	0.076*	0.535 (5)
H14B	0.4218	0.0165	0.3497	0.076*	0.535 (5)
C15	0.3929 (5)	0.1404 (4)	0.4308 (4)	0.0783 (18)	0.535 (5)
H15A	0.4165	0.2156	0.4450	0.117*	0.535 (5)
H15B	0.4130	0.0983	0.4870	0.117*	0.535 (5)
H15C	0.3139	0.1382	0.3997	0.117*	0.535 (5)
C14'	0.4494 (2)	0.0907 (2)	0.36797 (17)	0.0630 (7)	0.465 (5)
H14C	0.3806	0.0648	0.3727	0.076*	0.465 (5)
H14D	0.4895	0.1327	0.4232	0.076*	0.465 (5)
C15'	0.5185 (4)	−0.0066 (5)	0.3586 (4)	0.0661 (18)	0.465 (5)
H15D	0.4760	−0.0507	0.3063	0.099*	0.465 (5)
H15E	0.5392	−0.0508	0.4137	0.099*	0.465 (5)
H15F	0.5840	0.0200	0.3498	0.099*	0.465 (5)
C16	−0.24076 (16)	0.27283 (18)	0.22484 (13)	0.0405 (5)
H16A	−0.2516	0.3478	0.2423	0.049*
H16B	−0.1881	0.2369	0.2787	0.049*
C17	−0.35059 (16)	0.21135 (18)	0.19642 (16)	0.0469 (5)
H17A	−0.3805	0.2189	0.2453	0.056*
H17B	−0.4023	0.2462	0.1415	0.056*
C18	−0.34311 (17)	0.09051 (19)	0.17697 (15)	0.0474 (5)
C19	−0.4493 (2)	−0.0733 (2)	0.1242 (2)	0.0781 (8)
H19A	−0.4090	−0.1140	0.1802	0.094*
H19B	−0.4162	−0.0893	0.0784	0.094*
C20	−0.5684 (2)	−0.1065 (3)	0.0888 (2)	0.0875 (9)
H20A	−0.5997	−0.0926	0.1354	0.131*
H20B	−0.5743	−0.1839	0.0738	0.131*
H20C	−0.6078	−0.0644	0.0343	0.131*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0293 (8)	0.0359 (10)	0.0382 (9)	0.0042 (7)	0.0152 (7)	0.0047 (7)
N2	0.0345 (9)	0.0311 (9)	0.0487 (10)	0.0037 (7)	0.0162 (8)	0.0060 (7)
N3	0.0266 (8)	0.0378 (9)	0.0330 (9)	0.0045 (7)	0.0125 (7)	0.0041 (7)
N4	0.0339 (8)	0.0427 (10)	0.0364 (9)	0.0110 (7)	0.0127 (7)	0.0122 (7)
O1	0.0498 (9)	0.0516 (10)	0.0805 (11)	0.0080 (7)	0.0396 (9)	0.0247 (8)
O2	0.0554 (9)	0.0439 (9)	0.0648 (10)	−0.0008 (7)	0.0329 (8)	−0.0136 (7)
O3	0.0391 (8)	0.0594 (10)	0.0543 (9)	0.0214 (7)	0.0205 (7)	0.0126 (7)
O4	0.0458 (8)	0.0605 (10)	0.0330 (7)	0.0081 (7)	0.0188 (7)	0.0021 (7)
O5	0.0551 (10)	0.0536 (10)	0.0523 (10)	−0.0057 (8)	0.0110 (8)	0.0109 (8)
O6	0.0499 (10)	0.0648 (12)	0.0824 (13)	−0.0122 (9)	0.0035 (9)	0.0279 (9)
O7	0.0405 (9)	0.0445 (10)	0.0980 (13)	−0.0007 (7)	0.0236 (8)	0.0025 (9)
O8	0.0405 (9)	0.0515 (11)	0.1141 (15)	0.0092 (8)	0.0203 (9)	0.0085 (10)
C1	0.0290 (10)	0.0394 (12)	0.0408 (11)	0.0049 (8)	0.0121 (9)	0.0094 (9)
C2	0.0278 (9)	0.0405 (11)	0.0342 (10)	−0.0026 (9)	0.0079 (8)	−0.0037 (9)
C3	0.0266 (9)	0.0341 (11)	0.0306 (10)	−0.0001 (8)	0.0090 (8)	0.0030 (8)
C4	0.0272 (9)	0.0313 (11)	0.0362 (10)	0.0040 (8)	0.0106 (8)	0.0065 (8)
C5	0.0266 (9)	0.0310 (10)	0.0356 (10)	0.0033 (8)	0.0115 (8)	−0.0016 (8)
C6	0.0264 (9)	0.0292 (10)	0.0329 (10)	0.0021 (8)	0.0093 (8)	0.0062 (8)
C7	0.0289 (10)	0.0373 (11)	0.0363 (11)	0.0031 (8)	0.0116 (8)	0.0008 (9)
C8	0.0283 (9)	0.0379 (11)	0.0279 (10)	−0.0010 (8)	0.0065 (8)	−0.0055 (8)
C9	0.0396 (11)	0.0669 (16)	0.0326 (11)	−0.0044 (11)	0.0066 (9)	0.0062 (10)
C10	0.0457 (12)	0.0388 (13)	0.0668 (15)	−0.0017 (10)	0.0200 (11)	−0.0154 (11)
C11	0.0398 (11)	0.0504 (14)	0.0375 (11)	0.0086 (10)	0.0176 (9)	0.0022 (9)
C12	0.0345 (11)	0.0511 (14)	0.0563 (13)	0.0110 (10)	0.0224 (10)	0.0117 (10)
C13	0.0289 (10)	0.0436 (13)	0.0598 (14)	0.0097 (10)	0.0156 (10)	0.0118 (10)
C14	0.0651 (16)	0.0636 (17)	0.0525 (15)	0.0010 (13)	0.0117 (12)	0.0145 (12)
C15	0.103 (4)	0.066 (4)	0.074 (4)	0.001 (3)	0.041 (3)	0.015 (3)
C14'	0.0651 (16)	0.0636 (17)	0.0525 (15)	0.0010 (13)	0.0117 (12)	0.0145 (12)
C15'	0.056 (3)	0.073 (4)	0.061 (4)	0.006 (3)	0.012 (3)	0.018 (3)
C16	0.0394 (11)	0.0480 (13)	0.0375 (11)	0.0022 (9)	0.0179 (9)	0.0009 (9)
C17	0.0381 (12)	0.0509 (14)	0.0612 (14)	0.0027 (10)	0.0293 (11)	0.0054 (11)
C18	0.0371 (12)	0.0495 (14)	0.0578 (14)	0.0024 (10)	0.0197 (10)	0.0132 (11)
C19	0.0594 (16)	0.0461 (17)	0.126 (3)	−0.0032 (13)	0.0294 (16)	0.0016 (15)
C20	0.0692 (19)	0.065 (2)	0.125 (3)	−0.0134 (15)	0.0300 (18)	−0.0078 (17)

Geometric parameters (Å, º)

N1—C1	1.343 (3)	C9—H9B	0.9600
N1—C4	1.445 (2)	C9—H9C	0.9600
N1—C11	1.467 (2)	C10—H10A	0.9600
N2—C2	1.376 (2)	C10—H10B	0.9600
N2—C1	1.396 (2)	C10—H10C	0.9600
N2—H2A	0.8600	C11—C12	1.517 (3)
N3—C7	1.345 (2)	C11—H11A	0.9700
N3—C6	1.445 (2)	C11—H11B	0.9700
N3—C16	1.468 (2)	C12—C13	1.500 (3)
N4—C8	1.359 (2)	C12—H12A	0.9700
N4—C7	1.407 (2)	C12—H12B	0.9700
N4—H4A	0.8600	C14—C15	1.532 (5)
O1—C1	1.225 (2)	C14—H14A	0.9700
O2—C2	1.216 (2)	C14—H14B	0.9700
O3—C7	1.217 (2)	C15—H15A	0.9600
O4—C8	1.223 (2)	C15—H15B	0.9600
O5—C13	1.333 (3)	C15—H15C	0.9600
O5—C14	1.471 (3)	C15'—H15D	0.9600
O6—C13	1.200 (3)	C15'—H15E	0.9600
O7—C18	1.340 (3)	C15'—H15F	0.9600
O7—C19	1.455 (3)	C16—C17	1.520 (3)
O8—C18	1.199 (2)	C16—H16A	0.9700
C2—C3	1.512 (3)	C16—H16B	0.9700
C3—C9	1.527 (3)	C17—C18	1.502 (3)
C3—C4	1.540 (3)	C17—H17A	0.9700
C3—C6	1.576 (2)	C17—H17B	0.9700
C4—C5	1.575 (2)	C19—C20	1.491 (4)
C4—H4	0.9800	C19—H19A	0.9700
C5—C8	1.513 (3)	C19—H19B	0.9700
C5—C10	1.525 (3)	C20—H20A	0.9600
C5—C6	1.538 (2)	C20—H20B	0.9600
C6—H6	0.9800	C20—H20C	0.9600
C9—H9A	0.9600
C1—N1—C4	121.32 (15)	C5—C10—H10B	109.5
C1—N1—C11	117.69 (16)	H10A—C10—H10B	109.5
C4—N1—C11	119.98 (16)	C5—C10—H10C	109.5
C2—N2—C1	127.65 (17)	H10A—C10—H10C	109.5
C2—N2—H2A	116.2	H10B—C10—H10C	109.5
C1—N2—H2A	116.2	N1—C11—C12	112.29 (17)
C7—N3—C6	121.21 (15)	N1—C11—H11A	109.1
C7—N3—C16	118.10 (15)	C12—C11—H11A	109.1
C6—N3—C16	119.55 (15)	N1—C11—H11B	109.1
C8—N4—C7	128.42 (16)	C12—C11—H11B	109.1
C8—N4—H4A	115.8	H11A—C11—H11B	107.9
C7—N4—H4A	115.8	C13—C12—C11	111.87 (17)
C13—O5—C14	116.91 (18)	C13—C12—H12A	109.2
C18—O7—C19	116.79 (18)	C11—C12—H12A	109.2
O1—C1—N1	122.78 (18)	C13—C12—H12B	109.2
O1—C1—N2	119.97 (19)	C11—C12—H12B	109.2
N1—C1—N2	117.25 (16)	H12A—C12—H12B	107.9
O2—C2—N2	121.06 (19)	O6—C13—O5	123.9 (2)
O2—C2—C3	123.07 (17)	O6—C13—C12	124.1 (2)
N2—C2—C3	115.83 (16)	O5—C13—C12	112.00 (19)
C2—C3—C9	109.00 (16)	O5—C14—C15	109.3 (3)
C2—C3—C4	112.19 (15)	O5—C14—H14A	109.8
C9—C3—C4	117.88 (16)	C15—C14—H14A	109.8
C2—C3—C6	113.03 (14)	O5—C14—H14B	109.8
C9—C3—C6	117.47 (15)	C15—C14—H14B	109.8
C4—C3—C6	85.78 (13)	H14A—C14—H14B	108.3
N1—C4—C3	116.40 (15)	H15D—C15'—H15E	109.5
N1—C4—C5	122.39 (15)	H15D—C15'—H15F	109.5
C3—C4—C5	90.22 (13)	H15E—C15'—H15F	109.5
N1—C4—H4	108.8	N3—C16—C17	113.15 (17)
C3—C4—H4	108.8	N3—C16—H16A	108.9
C5—C4—H4	108.8	C17—C16—H16A	108.9
C8—C5—C10	109.76 (16)	N3—C16—H16B	108.9
C8—C5—C6	111.52 (15)	C17—C16—H16B	108.9
C10—C5—C6	117.22 (16)	H16A—C16—H16B	107.8
C8—C5—C4	112.06 (15)	C18—C17—C16	114.41 (17)
C10—C5—C4	118.63 (15)	C18—C17—H17A	108.7
C6—C5—C4	85.89 (13)	C16—C17—H17A	108.7
N3—C6—C5	116.51 (14)	C18—C17—H17B	108.7
N3—C6—C3	122.77 (15)	C16—C17—H17B	108.7
C5—C6—C3	90.26 (13)	H17A—C17—H17B	107.6
N3—C6—H6	108.6	O8—C18—O7	122.9 (2)
C5—C6—H6	108.6	O8—C18—C17	126.3 (2)
C3—C6—H6	108.6	O7—C18—C17	110.85 (18)
O3—C7—N3	124.14 (17)	O7—C19—C20	107.7 (2)
O3—C7—N4	119.11 (17)	O7—C19—H19A	110.2
N3—C7—N4	116.73 (16)	C20—C19—H19A	110.2
O4—C8—N4	121.48 (17)	O7—C19—H19B	110.2
O4—C8—C5	122.50 (17)	C20—C19—H19B	110.2
N4—C8—C5	116.00 (15)	H19A—C19—H19B	108.5
C3—C9—H9A	109.5	C19—C20—H20A	109.5
C3—C9—H9B	109.5	C19—C20—H20B	109.5
H9A—C9—H9B	109.5	H20A—C20—H20B	109.5
C3—C9—H9C	109.5	C19—C20—H20C	109.5
H9A—C9—H9C	109.5	H20A—C20—H20C	109.5
H9B—C9—H9C	109.5	H20B—C20—H20C	109.5
C5—C10—H10A	109.5
C4—N1—C1—O1	−176.76 (17)	C10—C5—C6—C3	140.95 (16)
C11—N1—C1—O1	−8.3 (3)	C4—C5—C6—C3	20.74 (13)
C4—N1—C1—N2	3.6 (3)	C2—C3—C6—N3	−31.2 (2)
C11—N1—C1—N2	172.08 (15)	C9—C3—C6—N3	97.2 (2)
C2—N2—C1—O1	−164.87 (18)	C4—C3—C6—N3	−143.50 (17)
C2—N2—C1—N1	14.8 (3)	C2—C3—C6—C5	91.11 (16)
C1—N2—C2—O2	172.13 (18)	C9—C3—C6—C5	−140.59 (17)
C1—N2—C2—C3	−5.6 (3)	C4—C3—C6—C5	−21.24 (13)
O2—C2—C3—C9	−63.8 (2)	C6—N3—C7—O3	−174.62 (18)
N2—C2—C3—C9	113.88 (18)	C16—N3—C7—O3	−6.8 (3)
O2—C2—C3—C4	163.75 (17)	C6—N3—C7—N4	6.6 (3)
N2—C2—C3—C4	−18.6 (2)	C16—N3—C7—N4	174.37 (16)
O2—C2—C3—C6	68.8 (2)	C8—N4—C7—O3	−170.17 (19)
N2—C2—C3—C6	−113.55 (17)	C8—N4—C7—N3	8.7 (3)
C1—N1—C4—C3	−28.0 (2)	C7—N4—C8—O4	179.36 (18)
C11—N1—C4—C3	163.74 (15)	C7—N4—C8—C5	1.0 (3)
C1—N1—C4—C5	80.6 (2)	C10—C5—C8—O4	−69.2 (2)
C11—N1—C4—C5	−87.6 (2)	C6—C5—C8—O4	159.16 (17)
C2—C3—C4—N1	34.4 (2)	C4—C5—C8—O4	64.8 (2)
C9—C3—C4—N1	−93.5 (2)	C10—C5—C8—N4	109.14 (18)
C6—C3—C4—N1	147.57 (15)	C6—C5—C8—N4	−22.5 (2)
C2—C3—C4—C5	−92.46 (16)	C4—C5—C8—N4	−116.85 (17)
C9—C3—C4—C5	139.68 (17)	C1—N1—C11—C12	84.8 (2)
C6—C3—C4—C5	20.71 (12)	C4—N1—C11—C12	−106.6 (2)
N1—C4—C5—C8	−31.6 (2)	N1—C11—C12—C13	69.6 (2)
C3—C4—C5—C8	90.32 (16)	C14—O5—C13—O6	1.1 (3)
N1—C4—C5—C10	97.9 (2)	C14—O5—C13—C12	−178.06 (18)
C3—C4—C5—C10	−140.14 (17)	C11—C12—C13—O6	33.5 (3)
N1—C4—C5—C6	−143.18 (17)	C11—C12—C13—O5	−147.36 (18)
C3—C4—C5—C6	−21.25 (13)	C13—O5—C14—C15	−95.7 (3)
C7—N3—C6—C5	−29.3 (2)	C7—N3—C16—C17	73.5 (2)
C16—N3—C6—C5	163.07 (16)	C6—N3—C16—C17	−118.47 (19)
C7—N3—C6—C3	79.8 (2)	N3—C16—C17—C18	64.6 (2)
C16—N3—C6—C3	−87.8 (2)	C19—O7—C18—O8	2.9 (3)
C8—C5—C6—N3	36.0 (2)	C19—O7—C18—C17	−178.0 (2)
C10—C5—C6—N3	−91.7 (2)	C16—C17—C18—O8	5.4 (3)
C4—C5—C6—N3	148.12 (16)	C16—C17—C18—O7	−173.61 (18)
C8—C5—C6—C3	−91.36 (16)	C18—O7—C19—C20	179.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4^i	0.86	2.32	3.148 (3)	163
N4—H4A···O1^i	0.86	2.01	2.795 (3)	151

Symmetry code: (i) −x, −y+1, −z.