Diethyl 2,6-diisobutyl-4,8-dioxo-2,3,6,7-tetra­hydro-1H,5H-2,3a,4a,6,7a,8a-hexa­azacyclo­penta­[def]­fluorene-8b,8c-dicarboxyl­ate

The mol­ecule of the title compound, C₂₂H₃₆N₆O₆, exhibits normal geometric parameters. Both imidazole rings adopt envelope conformations with the C=O group at the flap position. The triazinane rings adopt chair conformations.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.057
• wR factor = 0.176
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.41 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.54 Ratio
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         C2
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C11
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C20
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for       C20'

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C19
PLAT301_ALERT_3_C Main Residue  Disorder .........................      17.00 Perc.

   0 ALERT level A = In general: serious problem
   6 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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, 2000); software used to prepare material for publication: SHELXTL.

Diethyl 2,6-diisobutyl-4,8-dioxo-2,3,6,7-tetrahydro-1H,5H-2,3a,4a,6,7a,8a- hexaazacyclopenta[def]fluorene-8 b,8c-dicarboxylate

Crystal data

C22H36N6O6	F(000) = 1032
Mr = 480.57	Dx = 1.245 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6234 reflections
a = 13.7596 (9) Å	θ = 2.6–23.3°
b = 7.8469 (5) Å	µ = 0.09 mm^−1
c = 24.4168 (15) Å	T = 292 K
β = 103.476 (1)°	Block, colourless
V = 2563.7 (3) Å^3	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	5044 independent reflections
Radiation source: fine-focus sealed tube	3644 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −16→16
Tmin = 0.973, Tmax = 0.982	k = −9→9
19253 measured reflections	l = −30→28

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.176	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0971P)^2 + 0.2921P] where P = (Fo^2 + 2Fc^2)/3
5044 reflections	(Δ/σ)max = 0.001
380 parameters	Δρmax = 0.30 e Å^−3
40 restraints	Δρmin = −0.33 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	0.6078 (9)	0.2360 (17)	0.5160 (6)	0.162 (6)	0.605 (16)
H1A	0.6571	0.1510	0.5307	0.243*	0.605 (16)
H1B	0.5431	0.1962	0.5187	0.243*	0.605 (16)
H1C	0.6235	0.3393	0.5373	0.243*	0.605 (16)
C2	0.6072 (6)	0.2693 (14)	0.4564 (5)	0.097 (3)	0.605 (16)
H2A	0.5992	0.1583	0.4374	0.117*	0.605 (16)
C3	0.5203 (12)	0.375 (3)	0.4275 (9)	0.180 (8)	0.605 (16)
H3A	0.5238	0.4845	0.4455	0.270*	0.605 (16)
H3B	0.4593	0.3192	0.4298	0.270*	0.605 (16)
H3C	0.5218	0.3897	0.3887	0.270*	0.605 (16)
C1'	0.5873 (7)	0.1455 (19)	0.4744 (7)	0.113 (5)	0.395 (16)
H1D	0.6030	0.2019	0.5103	0.170*	0.395 (16)
H1E	0.6310	0.0497	0.4753	0.170*	0.395 (16)
H1F	0.5193	0.1069	0.4663	0.170*	0.395 (16)
C2'	0.6009 (12)	0.2675 (18)	0.4295 (7)	0.088 (4)	0.395 (16)
H2B	0.5938	0.2064	0.3938	0.106*	0.395 (16)
C3'	0.5229 (8)	0.410 (3)	0.4224 (9)	0.116 (6)	0.395 (16)
H3D	0.4578	0.3614	0.4193	0.174*	0.395 (16)
H3E	0.5234	0.4740	0.3889	0.174*	0.395 (16)
H3F	0.5385	0.4845	0.4545	0.174*	0.395 (16)
C4	0.70277 (18)	0.3470 (3)	0.44601 (11)	0.0677 (6)
H4A	0.6932	0.3721	0.4062	0.081*	0.605 (16)
H4B	0.7162	0.4535	0.4665	0.081*	0.605 (16)
H4C	0.7133	0.4441	0.4713	0.081*	0.395 (16)
H4D	0.7039	0.3896	0.4089	0.081*	0.395 (16)
C5	0.88176 (15)	0.3233 (3)	0.48549 (8)	0.0538 (5)
H5A	0.9300	0.2429	0.5064	0.065*
H5B	0.8712	0.4111	0.5115	0.065*
C6	0.79944 (18)	0.1130 (3)	0.42091 (10)	0.0613 (6)
H6A	0.7348	0.0630	0.4043	0.074*
H6B	0.8434	0.0222	0.4388	0.074*
C7	0.78076 (16)	0.2591 (3)	0.32769 (9)	0.0569 (5)
C8	0.90165 (13)	0.5665 (2)	0.42265 (8)	0.0444 (4)
C9	0.93061 (14)	0.2890 (2)	0.39506 (8)	0.0451 (4)
C10	1.02286 (17)	0.1743 (3)	0.41259 (10)	0.0578 (5)
C11	1.1985 (2)	0.1720 (4)	0.44175 (12)	0.0892 (9)
H11A	1.1860	0.0690	0.4610	0.107*	0.687 (10)
H11B	1.2445	0.2422	0.4686	0.107*	0.687 (10)
H11C	1.1918	0.1001	0.4729	0.107*	0.313 (10)
H11D	1.2090	0.1018	0.4119	0.107*	0.313 (10)
C12'	1.2871 (6)	0.275 (2)	0.4430 (11)	0.197 (12)	0.313 (10)
H12F	1.3457	0.2053	0.4540	0.295*	0.313 (10)
H12E	1.2903	0.3662	0.4697	0.295*	0.313 (10)
H12D	1.2837	0.3219	0.4063	0.295*	0.313 (10)
C12	1.2442 (4)	0.1269 (9)	0.3958 (2)	0.117 (3)	0.687 (10)
H12A	1.2531	0.2278	0.3752	0.175*	0.687 (10)
H12B	1.2017	0.0484	0.3710	0.175*	0.687 (10)
H12C	1.3079	0.0746	0.4106	0.175*	0.687 (10)
C13	0.92938 (14)	0.4159 (2)	0.34554 (8)	0.0454 (4)
C14	1.01691 (15)	0.3964 (3)	0.31680 (8)	0.0509 (5)
C15	1.15994 (18)	0.5251 (4)	0.29714 (11)	0.0748 (7)
H15A	1.1383	0.5658	0.2587	0.090*
H15B	1.1850	0.4098	0.2963	0.090*
C16	1.2382 (3)	0.6357 (5)	0.32920 (17)	0.1163 (12)
H16A	1.2122	0.7488	0.3305	0.174*
H16B	1.2934	0.6387	0.3113	0.174*
H16C	1.2605	0.5925	0.3668	0.174*
C17	0.79457 (19)	0.5101 (3)	0.26603 (9)	0.0674 (6)
H17A	0.8369	0.5270	0.2398	0.081*
H17B	0.7292	0.4751	0.2445	0.081*
C18	0.87873 (18)	0.7177 (3)	0.33024 (9)	0.0608 (6)
H18A	0.8688	0.8185	0.3513	0.073*
H18B	0.9257	0.7468	0.3076	0.073*
C19	0.7000 (2)	0.6814 (4)	0.31981 (12)	0.0917 (9)
H19A	0.6664	0.5718	0.3158	0.110*	0.542 (11)
H19B	0.7258	0.7010	0.3598	0.110*	0.542 (11)
H19C	0.6985	0.5778	0.3413	0.110*	0.458 (11)
H19D	0.7119	0.7751	0.3464	0.110*	0.458 (11)
C20	0.6260 (4)	0.8123 (9)	0.2983 (3)	0.079 (2)	0.542 (11)
H20A	0.6625	0.9203	0.3056	0.095*	0.542 (11)
C20'	0.6041 (4)	0.7055 (12)	0.2835 (3)	0.071 (2)	0.458 (11)
H20B	0.5823	0.5914	0.2695	0.085*	0.458 (11)
C21	0.5797 (18)	0.811 (4)	0.2334 (12)	0.136 (8)	0.542 (11)
H21A	0.6298	0.7777	0.2139	0.205*	0.542 (11)
H21B	0.5559	0.9233	0.2214	0.205*	0.542 (11)
H21C	0.5251	0.7320	0.2250	0.205*	0.542 (11)
C21'	0.5953 (17)	0.809 (4)	0.2332 (10)	0.107 (7)	0.458 (11)
H21D	0.6363	0.7621	0.2102	0.160*	0.458 (11)
H21E	0.6169	0.9234	0.2439	0.160*	0.458 (11)
H21F	0.5269	0.8111	0.2124	0.160*	0.458 (11)
C22	0.5473 (8)	0.8202 (17)	0.3341 (6)	0.119 (4)	0.542 (11)
H22A	0.5803	0.8176	0.3733	0.179*	0.542 (11)
H22B	0.5031	0.7242	0.3253	0.179*	0.542 (11)
H22C	0.5095	0.9237	0.3259	0.179*	0.542 (11)
C22'	0.5272 (8)	0.764 (2)	0.3145 (5)	0.111 (4)	0.458 (11)
H22D	0.5342	0.6996	0.3486	0.167*	0.458 (11)
H22E	0.4614	0.7472	0.2911	0.167*	0.458 (11)
H22F	0.5370	0.8830	0.3235	0.167*	0.458 (11)
N1	0.78795 (13)	0.2351 (2)	0.46334 (8)	0.0587 (5)
N2	0.78468 (15)	0.6703 (3)	0.29336 (8)	0.0687 (5)
N3	0.84068 (13)	0.1894 (2)	0.37575 (7)	0.0521 (4)
N4	0.92313 (11)	0.40195 (19)	0.44113 (6)	0.0434 (4)
N5	0.83704 (12)	0.3724 (2)	0.30533 (7)	0.0538 (4)
N6	0.92222 (12)	0.58178 (19)	0.37018 (6)	0.0473 (4)
O1	0.69406 (13)	0.2218 (2)	0.30738 (7)	0.0795 (5)
O2	0.87366 (11)	0.68019 (18)	0.44891 (6)	0.0569 (4)
O3	1.01839 (16)	0.0243 (2)	0.41805 (12)	0.1069 (8)
O4	1.10521 (11)	0.2636 (2)	0.42225 (6)	0.0611 (4)
O5	1.02609 (13)	0.2701 (2)	0.29077 (7)	0.0762 (5)
O6	1.07661 (11)	0.52751 (19)	0.32473 (6)	0.0605 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.154 (8)	0.183 (10)	0.183 (12)	0.064 (7)	0.110 (8)	0.078 (9)
C2	0.056 (3)	0.111 (5)	0.127 (6)	0.001 (3)	0.028 (4)	0.001 (5)
C3	0.157 (10)	0.191 (11)	0.192 (11)	0.001 (7)	0.038 (8)	−0.017 (8)
C1'	0.083 (5)	0.131 (8)	0.140 (9)	−0.003 (5)	0.055 (5)	0.053 (7)
C2'	0.082 (6)	0.082 (6)	0.101 (7)	−0.003 (4)	0.021 (6)	0.018 (6)
C3'	0.032 (4)	0.159 (13)	0.153 (12)	0.022 (5)	0.012 (5)	0.055 (10)
C4	0.0681 (15)	0.0681 (15)	0.0712 (14)	0.0018 (11)	0.0249 (12)	0.0022 (12)
C5	0.0602 (12)	0.0567 (12)	0.0457 (11)	0.0002 (9)	0.0150 (9)	0.0038 (9)
C6	0.0650 (13)	0.0500 (12)	0.0736 (14)	−0.0090 (10)	0.0255 (11)	0.0017 (11)
C7	0.0580 (13)	0.0575 (12)	0.0548 (12)	−0.0071 (10)	0.0121 (10)	−0.0133 (10)
C8	0.0433 (10)	0.0439 (10)	0.0454 (10)	−0.0006 (8)	0.0090 (8)	−0.0044 (8)
C9	0.0496 (11)	0.0398 (10)	0.0475 (10)	0.0002 (8)	0.0146 (8)	−0.0011 (8)
C10	0.0623 (14)	0.0486 (12)	0.0677 (14)	0.0092 (10)	0.0256 (11)	0.0058 (10)
C11	0.0643 (16)	0.121 (2)	0.0836 (18)	0.0394 (16)	0.0193 (13)	0.0182 (17)
C12'	0.099 (11)	0.20 (2)	0.27 (3)	0.043 (12)	0.004 (13)	0.032 (19)
C12	0.093 (4)	0.170 (6)	0.098 (4)	0.059 (4)	0.046 (3)	0.029 (4)
C13	0.0507 (11)	0.0437 (10)	0.0430 (10)	0.0012 (8)	0.0130 (8)	−0.0034 (8)
C14	0.0568 (11)	0.0525 (12)	0.0450 (10)	0.0007 (9)	0.0155 (9)	−0.0023 (9)
C15	0.0639 (14)	0.0826 (17)	0.0878 (17)	0.0003 (13)	0.0378 (13)	0.0154 (14)
C16	0.089 (2)	0.122 (3)	0.147 (3)	−0.032 (2)	0.045 (2)	−0.006 (2)
C17	0.0648 (14)	0.0861 (17)	0.0479 (12)	0.0051 (12)	0.0065 (10)	0.0074 (11)
C18	0.0776 (15)	0.0491 (12)	0.0589 (13)	0.0114 (10)	0.0222 (11)	0.0103 (10)
C19	0.0775 (18)	0.120 (2)	0.0828 (18)	0.0376 (17)	0.0285 (15)	0.0288 (17)
C20	0.074 (3)	0.054 (4)	0.107 (4)	0.005 (3)	0.018 (3)	−0.005 (3)
C20'	0.052 (3)	0.069 (5)	0.086 (4)	−0.003 (3)	0.006 (3)	−0.009 (3)
C21	0.111 (13)	0.149 (15)	0.142 (15)	0.035 (9)	0.016 (10)	0.025 (12)
C21'	0.058 (5)	0.137 (14)	0.097 (10)	0.002 (6)	−0.039 (6)	0.050 (10)
C22	0.094 (6)	0.119 (6)	0.152 (8)	0.019 (5)	0.042 (6)	−0.012 (6)
C22'	0.063 (5)	0.159 (13)	0.108 (8)	0.019 (6)	0.014 (5)	−0.004 (7)
N1	0.0581 (11)	0.0594 (11)	0.0635 (11)	−0.0028 (8)	0.0245 (9)	0.0005 (9)
N2	0.0679 (12)	0.0788 (14)	0.0600 (11)	0.0213 (10)	0.0158 (9)	0.0151 (10)
N3	0.0565 (10)	0.0443 (9)	0.0577 (10)	−0.0071 (7)	0.0179 (8)	−0.0055 (7)
N4	0.0478 (8)	0.0423 (8)	0.0413 (8)	0.0022 (7)	0.0125 (6)	−0.0002 (7)
N5	0.0523 (10)	0.0599 (10)	0.0475 (9)	−0.0028 (8)	0.0079 (7)	−0.0028 (8)
N6	0.0599 (10)	0.0397 (8)	0.0451 (9)	0.0033 (7)	0.0177 (7)	0.0015 (7)
O1	0.0623 (10)	0.0950 (13)	0.0758 (11)	−0.0253 (9)	0.0050 (8)	−0.0140 (9)
O2	0.0715 (10)	0.0487 (8)	0.0535 (8)	0.0051 (7)	0.0205 (7)	−0.0089 (6)
O3	0.0888 (14)	0.0530 (11)	0.183 (2)	0.0176 (9)	0.0395 (14)	0.0259 (12)
O4	0.0519 (8)	0.0698 (10)	0.0615 (9)	0.0137 (7)	0.0133 (7)	0.0060 (7)
O5	0.0833 (12)	0.0766 (11)	0.0789 (11)	−0.0043 (9)	0.0395 (9)	−0.0260 (9)
O6	0.0591 (9)	0.0583 (9)	0.0705 (9)	−0.0032 (7)	0.0279 (7)	0.0026 (7)

Geometric parameters (Å, º)

C1—C2	1.476 (8)	C12'—H12F	0.96
C1—H1A	0.96	C12'—H12E	0.96
C1—H1B	0.96	C12'—H12D	0.96
C1—H1C	0.96	C12—H12A	0.96
C2—C3	1.49 (2)	C12—H12B	0.96
C2—C4	1.523 (9)	C12—H12C	0.96
C2—H2A	0.98	C13—N6	1.447 (2)
C3—H3A	0.96	C13—N5	1.454 (2)
C3—H3B	0.96	C13—C14	1.536 (3)
C3—H3C	0.96	C14—O5	1.199 (2)
C1'—C2'	1.499 (8)	C14—O6	1.303 (3)
C1'—H1D	0.96	C15—O6	1.459 (3)
C1'—H1E	0.96	C15—C16	1.461 (4)
C1'—H1F	0.96	C15—H15A	0.97
C2'—C4	1.501 (15)	C15—H15B	0.97
C2'—C3'	1.53 (3)	C16—H16A	0.96
C2'—H2B	0.98	C16—H16B	0.96
C3'—H3D	0.96	C16—H16C	0.96
C3'—H3E	0.96	C17—N2	1.444 (3)
C3'—H3F	0.96	C17—N5	1.473 (3)
C4—N1	1.447 (3)	C17—H17A	0.97
C4—H4A	0.97	C17—H17B	0.97
C4—H4B	0.97	C18—N2	1.443 (3)
C4—H4C	0.97	C18—N6	1.475 (3)
C4—H4D	0.97	C18—H18A	0.97
C5—N1	1.453 (3)	C18—H18B	0.97
C5—N4	1.472 (2)	C19—C20'	1.421 (5)
C5—H5A	0.97	C19—C20	1.456 (5)
C5—H5B	0.97	C19—N2	1.460 (3)
C6—N1	1.446 (3)	C19—H19A	0.97
C6—N3	1.479 (3)	C19—H19B	0.97
C6—H6A	0.97	C19—H19C	0.97
C6—H6B	0.97	C19—H19D	0.97
C7—O1	1.216 (3)	C20—C22	1.544 (13)
C7—N5	1.373 (3)	C20—C21	1.56 (2)
C7—N3	1.380 (3)	C20—H20A	0.98
C8—O2	1.212 (2)	C20'—C21'	1.45 (2)
C8—N4	1.377 (2)	C20'—C22'	1.509 (8)
C8—N6	1.380 (2)	C20'—H20B	0.98
C9—N3	1.447 (2)	C21—H21A	0.96
C9—N4	1.454 (2)	C21—H21B	0.96
C9—C10	1.533 (3)	C21—H21C	0.96
C9—C13	1.563 (3)	C21'—H21D	0.96
C10—O3	1.187 (3)	C21'—H21E	0.96
C10—O4	1.306 (3)	C21'—H21F	0.96
C11—O4	1.451 (3)	C22—H22A	0.96
C11—C12	1.453 (5)	C22—H22B	0.96
C11—C12'	1.458 (8)	C22—H22C	0.96
C11—H11A	0.97	C22'—H22D	0.96
C11—H11B	0.97	C22'—H22E	0.96
C11—H11C	0.97	C22'—H22F	0.96
C11—H11D	0.95
C1—C2—C3	112.6 (11)	O5—C14—O6	126.2 (2)
C1—C2—C4	115.4 (7)	O5—C14—C13	120.99 (19)
C3—C2—C4	109.1 (10)	O6—C14—C13	112.81 (17)
C1—C2—H2A	106.4	O6—C15—C16	107.8 (2)
C3—C2—H2A	106.4	O6—C15—H15A	110.1
C4—C2—H2A	106.4	C16—C15—H15A	110.1
C2'—C1'—H1D	109.5	O6—C15—H15B	110.1
C2'—C1'—H1E	109.5	C16—C15—H15B	110.1
H1D—C1'—H1E	109.5	H15A—C15—H15B	108.5
C2'—C1'—H1F	109.5	C15—C16—H16A	109.5
H1D—C1'—H1F	109.5	C15—C16—H16B	109.5
H1E—C1'—H1F	109.5	H16A—C16—H16B	109.5
C1'—C2'—C4	109.7 (9)	C15—C16—H16C	109.5
C1'—C2'—C3'	110.3 (12)	H16A—C16—H16C	109.5
C4—C2'—C3'	108.2 (12)	H16B—C16—H16C	109.5
C1'—C2'—H2B	109.6	N2—C17—N5	113.79 (17)
C4—C2'—H2B	109.6	N2—C17—H17A	108.8
C3'—C2'—H2B	109.6	N5—C17—H17A	108.8
C2'—C3'—H3D	109.5	N2—C17—H17B	108.8
C2'—C3'—H3E	109.5	N5—C17—H17B	108.8
H3D—C3'—H3E	109.5	H17A—C17—H17B	107.7
C2'—C3'—H3F	109.5	N2—C18—N6	113.11 (18)
H3D—C3'—H3F	109.5	N2—C18—H18A	109.0
H3E—C3'—H3F	109.5	N6—C18—H18A	109.0
N1—C4—C2'	118.0 (6)	N2—C18—H18B	109.0
N1—C4—C2	112.4 (4)	N6—C18—H18B	109.0
N1—C4—H4A	109.1	H18A—C18—H18B	107.8
C2'—C4—H4A	85.2	C20'—C19—N2	116.9 (3)
C2—C4—H4A	109.1	C20—C19—N2	116.5 (3)
N1—C4—H4B	109.1	C20'—C19—H19A	72.7
C2'—C4—H4B	123.4	C20—C19—H19A	108.2
C2—C4—H4B	109.1	N2—C19—H19A	108.2
H4A—C4—H4B	107.9	C20'—C19—H19B	132.5
N1—C4—H4C	107.5	C20—C19—H19B	108.2
C2'—C4—H4C	119.3	N2—C19—H19B	108.2
C2—C4—H4C	102.5	H19A—C19—H19B	107.3
H4A—C4—H4C	116.2	C20'—C19—H19C	108.4
N1—C4—H4D	107.1	C20—C19—H19C	133.2
C2'—C4—H4D	96.3	N2—C19—H19C	108.0
C2—C4—H4D	119.7	H19B—C19—H19C	68.8
H4B—C4—H4D	98.2	C20'—C19—H19D	107.7
H4C—C4—H4D	106.9	C20—C19—H19D	72.6
N1—C5—N4	112.84 (15)	N2—C19—H19D	108.3
N1—C5—H5A	109.0	H19A—C19—H19D	138.0
N4—C5—H5A	109.0	H19C—C19—H19D	107.2
N1—C5—H5B	109.0	C19—C20—C22	110.4 (7)
N4—C5—H5B	109.0	C19—C20—C21	116.6 (12)
H5A—C5—H5B	107.8	C22—C20—C21	113.6 (12)
N1—C6—N3	112.99 (17)	C22—C20—H19D	95.4
N1—C6—H6A	109.0	C21—C20—H19D	149.3
N3—C6—H6A	109.0	C19—C20—H20A	105.0
N1—C6—H6B	109.0	C22—C20—H20A	105.0
N3—C6—H6B	109.0	C21—C20—H20A	105.0
H6A—C6—H6B	107.8	H19D—C20—H20A	75.3
O1—C7—N5	125.7 (2)	C19—C20'—C21'	119.0 (10)
O1—C7—N3	125.9 (2)	C19—C20'—C22'	112.7 (6)
N5—C7—N3	108.30 (17)	C21'—C20'—C22'	108.8 (15)
O2—C8—N4	125.93 (17)	C19—C20'—H20B	105.1
O2—C8—N6	125.90 (17)	C21'—C20'—H20B	105.1
N4—C8—N6	108.10 (15)	C22'—C20'—H20B	105.1
N3—C9—N4	111.83 (15)	C20—C21—H21A	109.5
N3—C9—C10	111.30 (16)	C20—C21—H21B	109.5
N4—C9—C10	110.19 (15)	H21A—C21—H21B	109.5
N3—C9—C13	103.75 (14)	C20—C21—H21C	109.5
N4—C9—C13	102.73 (14)	H21A—C21—H21C	109.5
C10—C9—C13	116.67 (16)	H21B—C21—H21C	109.5
O3—C10—O4	125.2 (2)	C20'—C21'—H21D	109.5
O3—C10—C9	123.5 (2)	C20'—C21'—H21E	109.5
O4—C10—C9	111.24 (17)	H21D—C21'—H21E	109.5
O4—C11—C12	112.1 (3)	C20'—C21'—H21F	109.5
O4—C11—C12'	113.8 (6)	H21D—C21'—H21F	109.5
C12—C11—C12'	69.0 (10)	H21E—C21'—H21F	109.5
O4—C11—H11A	109.2	C20—C22—H22A	109.5
C12—C11—H11A	109.2	C20—C22—H22B	109.5
C12'—C11—H11A	133.9	H22A—C22—H22B	109.5
O4—C11—H11B	109.2	C20—C22—H22C	109.5
C12—C11—H11B	109.2	H22A—C22—H22C	109.5
H11A—C11—H11B	107.9	H22B—C22—H22C	109.5
O4—C11—H11C	108.0	C20'—C22'—H22D	109.5
C12—C11—H11C	127.0	C20'—C22'—H22E	109.5
C12'—C11—H11C	122.6	H22D—C22'—H22E	109.5
H11B—C11—H11C	88.1	C20'—C22'—H22F	109.5
O4—C11—H11D	108.4	H22D—C22'—H22F	109.5
C12'—C11—H11D	93.6	H22E—C22'—H22F	109.5
H11A—C11—H11D	87.9	C6—N1—C4	114.12 (18)
H11B—C11—H11D	130.9	C6—N1—C5	110.25 (16)
H11C—C11—H11D	108.8	C4—N1—C5	114.12 (18)
C11—C12'—H12F	109.5	C18—N2—C17	110.23 (18)
C11—C12'—H12E	109.5	C18—N2—C19	113.6 (2)
H12F—C12'—H12E	109.5	C17—N2—C19	115.3 (2)
C11—C12'—H12D	109.5	C7—N3—C9	111.05 (16)
H12F—C12'—H12D	109.5	C7—N3—C6	122.50 (18)
H12E—C12'—H12D	109.5	C9—N3—C6	115.06 (16)
C11—C12—H12A	109.5	C8—N4—C9	111.50 (14)
H11D—C12—H12A	134.1	C8—N4—C5	122.98 (16)
C11—C12—H12B	109.5	C9—N4—C5	115.02 (15)
H11D—C12—H12B	77.4	C7—N5—C13	111.64 (16)
C11—C12—H12C	109.5	C7—N5—C17	124.00 (18)
H11D—C12—H12C	110.3	C13—N5—C17	114.78 (17)
N6—C13—N5	111.02 (16)	C8—N6—C13	110.89 (14)
N6—C13—C14	114.59 (16)	C8—N6—C18	122.49 (16)
N5—C13—C14	108.84 (15)	C13—N6—C18	115.61 (15)
N6—C13—C9	103.93 (14)	C10—O4—C11	117.2 (2)
N5—C13—C9	102.89 (15)	C14—O6—C15	117.20 (17)
C14—C13—C9	114.93 (15)
C1'—C2'—C4—N1	50.5 (12)	N5—C7—N3—C9	16.0 (2)
C3'—C2'—C4—N1	170.8 (10)	O1—C7—N3—C6	−25.1 (3)
C1'—C2'—C4—C2	−32.2 (16)	N5—C7—N3—C6	157.52 (18)
C3'—C2'—C4—C2	88 (3)	N4—C9—N3—C7	99.74 (18)
C1—C2—C4—N1	63.2 (9)	C10—C9—N3—C7	−136.53 (18)
C3—C2—C4—N1	−169.0 (11)	C13—C9—N3—C7	−10.3 (2)
C1—C2—C4—C2'	172 (3)	N4—C9—N3—C6	−44.9 (2)
C3—C2—C4—C2'	−60 (2)	C10—C9—N3—C6	78.8 (2)
N3—C9—C10—O3	−11.2 (3)	C13—C9—N3—C6	−154.91 (16)
N4—C9—C10—O3	113.5 (3)	N1—C6—N3—C7	−89.5 (2)
C13—C9—C10—O3	−130.0 (3)	N1—C6—N3—C9	50.7 (2)
N3—C9—C10—O4	170.85 (16)	O2—C8—N4—C9	165.91 (18)
N4—C9—C10—O4	−64.5 (2)	N6—C8—N4—C9	−17.0 (2)
C13—C9—C10—O4	52.1 (2)	O2—C8—N4—C5	23.0 (3)
N3—C9—C13—N6	117.03 (16)	N6—C8—N4—C5	−159.87 (16)
N4—C9—C13—N6	0.43 (17)	N3—C9—N4—C8	−100.78 (18)
C10—C9—C13—N6	−120.19 (18)	C10—C9—N4—C8	134.86 (16)
N3—C9—C13—N5	1.18 (18)	C13—C9—N4—C8	9.89 (18)
N4—C9—C13—N5	−115.41 (15)	N3—C9—N4—C5	45.2 (2)
C10—C9—C13—N5	123.97 (18)	C10—C9—N4—C5	−79.1 (2)
N3—C9—C13—C14	−116.95 (17)	C13—C9—N4—C5	155.91 (15)
N4—C9—C13—C14	126.45 (16)	N1—C5—N4—C8	90.7 (2)
C10—C9—C13—C14	5.8 (2)	N1—C5—N4—C9	−51.0 (2)
N6—C13—C14—O5	−173.73 (19)	O1—C7—N5—C13	167.5 (2)
N5—C13—C14—O5	−48.8 (3)	N3—C7—N5—C13	−15.2 (2)
C9—C13—C14—O5	66.0 (2)	O1—C7—N5—C17	23.2 (3)
N6—C13—C14—O6	6.9 (2)	N3—C7—N5—C17	−159.41 (18)
N5—C13—C14—O6	131.88 (18)	N6—C13—N5—C7	−102.33 (19)
C9—C13—C14—O6	−113.38 (18)	C14—C13—N5—C7	130.65 (18)
C20'—C19—C20—C22	85.1 (7)	C9—C13—N5—C7	8.3 (2)
N2—C19—C20—C22	−174.3 (5)	N6—C13—N5—C17	45.4 (2)
C20'—C19—C20—C21	−46.5 (13)	C14—C13—N5—C17	−81.6 (2)
N2—C19—C20—C21	54.1 (14)	C9—C13—N5—C17	156.06 (17)
C20—C19—C20'—C21'	64.4 (17)	N2—C17—N5—C7	92.4 (3)
N2—C19—C20'—C21'	−34.8 (17)	N2—C17—N5—C13	−50.9 (3)
C20—C19—C20'—C22'	−64.6 (9)	O2—C8—N6—C13	−165.70 (18)
N2—C19—C20'—C22'	−163.9 (8)	N4—C8—N6—C13	17.2 (2)
N3—C6—N1—C4	76.4 (2)	O2—C8—N6—C18	−23.4 (3)
N3—C6—N1—C5	−53.6 (2)	N4—C8—N6—C18	159.52 (17)
C2'—C4—N1—C6	59.6 (7)	N5—C13—N6—C8	99.41 (18)
C2—C4—N1—C6	86.0 (5)	C14—C13—N6—C8	−136.80 (16)
C2'—C4—N1—C5	−172.4 (7)	C9—C13—N6—C8	−10.6 (2)
C2—C4—N1—C5	−146.0 (5)	N5—C13—N6—C18	−45.7 (2)
N4—C5—N1—C6	53.9 (2)	C14—C13—N6—C18	78.1 (2)
N4—C5—N1—C4	−76.1 (2)	C9—C13—N6—C18	−155.68 (16)
N6—C18—N2—C17	−52.4 (2)	N2—C18—N6—C8	−89.8 (2)
N6—C18—N2—C19	78.8 (3)	N2—C18—N6—C13	50.9 (2)
N5—C17—N2—C18	52.9 (3)	O3—C10—O4—C11	−0.7 (4)
N5—C17—N2—C19	−77.4 (3)	C9—C10—O4—C11	177.26 (18)
C20'—C19—N2—C18	155.2 (5)	C12—C11—O4—C10	94.9 (4)
C20—C19—N2—C18	112.6 (5)	C12'—C11—O4—C10	170.8 (12)
C20'—C19—N2—C17	−76.2 (5)	O5—C14—O6—C15	3.3 (3)
C20—C19—N2—C17	−118.8 (5)	C13—C14—O6—C15	−177.44 (17)
O1—C7—N3—C9	−166.7 (2)	C16—C15—O6—C14	−155.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···O3	0.97	2.57	3.109 (3)	115
C20—H20A···O1^i	0.98	2.40	3.340 (8)	160

Symmetry code: (i) x, y+1, z.