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

The title compound, C₃₀H₃₆N₆O₆, is a glycoluril derivative with two ethyl acetate substituents on the convex face of the glycouril system. Two equivalent six-membered triazine rings bind the N atoms from separate rings of the glycouril unit to form the flexible sidewalls of a mol­ecular clip. One N atom from each ring caries a 4-methyl­benzyl substituent. The crystal structure is stabilized by inter­molecular C—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.064
• wR factor = 0.197
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for       C29'
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for       C27'

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.22 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.52 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C28'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C19'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C24'
PLAT301_ALERT_3_C Main Residue  Disorder .........................      19.00 Perc.
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C1
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      30.50 Deg.
              C19' -O6   -C19     1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  10 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
   9 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Diethyl 2,6-bis(4-methylbenzyl)-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

C30H36N6O6	F(000) = 1224
Mr = 576.65	Dx = 1.284 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5736 reflections
a = 16.9160 (8) Å	θ = 2.4–22.3°
b = 13.6411 (6) Å	µ = 0.09 mm^−1
c = 12.9597 (2) Å	T = 292 K
β = 94.160 (1)°	Block, colorless
V = 2982.6 (2) Å^3	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART 4K CCD area-detector diffractometer	3764 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.068
Graphite monochromator	θmax = 27.0°, θmin = 1.9°
φ and ω scans	h = −21→21
33094 measured reflections	k = −17→17
6504 independent reflections	l = −16→16

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.197	H-atom parameters constrained
S = 1.01	Please provide
6504 reflections	(Δ/σ)max < 0.001
455 parameters	Δρmax = 0.30 e Å^−3
95 restraints	Δρmin = −0.24 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	0.1488 (2)	0.6114 (3)	1.2997 (3)	0.1216 (13)
H1A	0.1929	0.6256	1.3481	0.182*
H1B	0.1247	0.5508	1.3183	0.182*
H1C	0.1106	0.6634	1.3008	0.182*
C2	0.17739 (17)	0.6025 (2)	1.1916 (3)	0.0825 (8)
C3	0.16737 (18)	0.5161 (2)	1.1373 (3)	0.0910 (9)
H3	0.1431	0.4632	1.1673	0.109*
C4	0.21362 (18)	0.6775 (2)	1.1457 (3)	0.0867 (9)
H4	0.2213	0.7364	1.1811	0.104*
C5	0.19305 (17)	0.5069 (2)	1.0380 (3)	0.0816 (9)
H5	0.1848	0.4482	1.0024	0.098*
C6	0.23943 (17)	0.6690 (2)	1.0479 (2)	0.0796 (8)
H6	0.2636	0.7224	1.0187	0.095*
C7	0.23035 (14)	0.58301 (18)	0.9920 (2)	0.0651 (7)
C8	0.26021 (15)	0.5743 (2)	0.8853 (2)	0.0712 (7)
H8A	0.2397	0.5146	0.8526	0.085*
H8B	0.2410	0.6293	0.8432	0.085*
C9	0.38054 (15)	0.48046 (19)	0.92974 (18)	0.0644 (7)
H9A	0.3525	0.4602	0.9889	0.077*
H9B	0.4357	0.4905	0.9534	0.077*
C10	0.38210 (15)	0.59895 (19)	0.7944 (2)	0.0683 (7)
H10A	0.3548	0.6563	0.7653	0.082*
H10B	0.4373	0.6165	0.8096	0.082*
C11	0.31452 (13)	0.33512 (16)	0.84443 (18)	0.0530 (6)
C12	0.31140 (13)	0.51139 (17)	0.64789 (18)	0.0550 (6)
C13	0.40439 (13)	0.42510 (16)	0.75289 (17)	0.0508 (5)
C14	0.49490 (13)	0.41024 (19)	0.75826 (17)	0.0572 (6)
C15	0.62090 (14)	0.4791 (2)	0.7402 (3)	0.0865 (9)
H15A	0.6422	0.4954	0.8096	0.104*
H15B	0.6362	0.4124	0.7253	0.104*
C16	0.65248 (19)	0.5461 (2)	0.6658 (3)	0.0954 (10)
H16A	0.6362	0.5249	0.5968	0.143*
H16B	0.7093	0.5465	0.6749	0.143*
H16C	0.6327	0.6110	0.6765	0.143*
C17	0.35785 (12)	0.35177 (16)	0.67906 (16)	0.0492 (5)
C18	0.40849 (13)	0.2853 (2)	0.6139 (2)	0.0633 (7)
C19	0.5019 (3)	0.2745 (4)	0.4962 (5)	0.0759 (14)	0.68
H19A	0.5250	0.2238	0.5413	0.091*	0.68
H19B	0.4728	0.2437	0.4376	0.091*	0.68
C20	0.5627 (5)	0.3386 (5)	0.4617 (6)	0.112 (2)	0.68
H20A	0.5385	0.3961	0.4306	0.168*	0.68
H20B	0.5920	0.3050	0.4119	0.168*	0.68
H20C	0.5979	0.3573	0.5198	0.168*	0.68
C19'	0.4942 (5)	0.3212 (8)	0.4627 (6)	0.056 (2)	0.32
H19C	0.4953	0.3793	0.4196	0.067*	0.32
H19D	0.4717	0.2673	0.4215	0.067*	0.32
C20'	0.5755 (5)	0.2963 (9)	0.5089 (9)	0.072 (3)	0.32
H20D	0.5982	0.3526	0.5441	0.107*	0.32
H20E	0.6082	0.2769	0.4550	0.107*	0.32
H20F	0.5720	0.2434	0.5572	0.107*	0.32
C21	0.24081 (14)	0.25072 (18)	0.6994 (2)	0.0642 (7)
H21A	0.2119	0.2190	0.7520	0.077*
H21B	0.2541	0.2014	0.6496	0.077*
C22	0.23384 (13)	0.3740 (2)	0.56892 (18)	0.0619 (6)
H22A	0.2011	0.4253	0.5364	0.074*
H22B	0.2452	0.3266	0.5161	0.074*
C23	0.1153 (2)	0.2968 (3)	0.6140 (3)	0.0672 (11)	0.60
H23A	0.1193	0.2450	0.5634	0.081*	0.60
H23B	0.0884	0.3516	0.5791	0.081*	0.60
C24	0.0637 (3)	0.2597 (4)	0.6986 (3)	0.0674 (17)	0.60
C25	0.0215 (3)	0.1727 (4)	0.6853 (4)	0.086 (2)	0.60
H25	0.0238	0.1370	0.6245	0.103*	0.60
C26	−0.0241 (3)	0.1390 (4)	0.7630 (5)	0.087 (2)	0.60
H26	−0.0523	0.0807	0.7541	0.105*	0.60
C27	−0.0274 (4)	0.1923 (5)	0.8539 (4)	0.094 (2)	0.60
C28	0.0148 (4)	0.2794 (4)	0.8671 (4)	0.098 (2)	0.60
H28	0.0125	0.3151	0.9280	0.118*	0.60
C29	0.0603 (3)	0.3131 (4)	0.7895 (4)	0.090 (2)	0.60
H29	0.0885	0.3713	0.7984	0.108*	0.60
C30	−0.0707 (4)	0.1486 (7)	0.9437 (6)	0.122 (3)	0.60
H30A	−0.0891	0.2006	0.9858	0.182*	0.60
H30B	−0.0349	0.1074	0.9851	0.182*	0.60
H30C	−0.1151	0.1104	0.9164	0.182*	0.60
C23'	0.1344 (3)	0.3647 (5)	0.6941 (5)	0.0688 (16)	0.40
H23C	0.1049	0.4072	0.6452	0.083*	0.40
H23D	0.1576	0.4061	0.7491	0.083*	0.40
C24'	0.0752 (5)	0.2963 (6)	0.7411 (8)	0.077 (3)	0.40
C25'	0.0443 (5)	0.2155 (7)	0.6871 (6)	0.085 (4)	0.40
H25'	0.0559	0.2054	0.6189	0.102*	0.40
C26'	−0.0038 (6)	0.1498 (7)	0.7350 (7)	0.104 (4)	0.40
H26'	−0.0245	0.0957	0.6988	0.125*	0.40
C27'	−0.0210 (7)	0.1649 (7)	0.8367 (8)	0.103 (4)	0.40
C28'	0.0099 (8)	0.2456 (8)	0.8907 (7)	0.149 (6)	0.40
H28'	−0.0016	0.2558	0.9589	0.179*	0.40
C29'	0.0580 (7)	0.3113 (7)	0.8428 (7)	0.156 (7)	0.40
H29'	0.0788	0.3655	0.8790	0.187*	0.40
C30'	−0.0766 (9)	0.0937 (11)	0.8887 (12)	0.158 (6)	0.40
H30D	−0.0457	0.0490	0.9323	0.236*	0.40
H30E	−0.1074	0.0574	0.8364	0.236*	0.40
H30F	−0.1115	0.1301	0.9296	0.236*	0.40
N1	0.34768 (12)	0.57253 (15)	0.89095 (17)	0.0653 (6)
N2	0.37579 (10)	0.40206 (14)	0.85312 (13)	0.0526 (5)
N3	0.37741 (10)	0.52059 (13)	0.71721 (14)	0.0545 (5)
N4	0.31281 (10)	0.29424 (13)	0.74679 (14)	0.0521 (5)
N5	0.30724 (10)	0.41589 (13)	0.61293 (13)	0.0505 (5)
N6	0.19131 (12)	0.32638 (16)	0.64762 (17)	0.0715 (6)
O1	0.27191 (10)	0.31311 (12)	0.91181 (12)	0.0680 (5)
O2	0.26710 (10)	0.57730 (12)	0.61946 (14)	0.0736 (5)
O3	0.52286 (10)	0.33102 (14)	0.78115 (16)	0.0847 (6)
O4	0.53408 (9)	0.48739 (13)	0.73355 (14)	0.0717 (5)
O5	0.40873 (12)	0.19732 (16)	0.61712 (17)	0.0949 (7)
O6	0.44897 (11)	0.33889 (15)	0.55302 (14)	0.0801 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.117 (3)	0.149 (3)	0.105 (3)	0.036 (2)	0.045 (2)	−0.003 (2)
C2	0.0678 (18)	0.088 (2)	0.094 (2)	0.0191 (16)	0.0206 (16)	−0.0106 (17)
C3	0.0750 (19)	0.080 (2)	0.122 (3)	−0.0002 (15)	0.0369 (19)	−0.0018 (19)
C4	0.084 (2)	0.081 (2)	0.097 (2)	0.0011 (16)	0.0182 (18)	−0.0314 (18)
C5	0.0757 (18)	0.0651 (17)	0.107 (2)	−0.0071 (14)	0.0242 (17)	−0.0184 (16)
C6	0.0794 (19)	0.0623 (17)	0.099 (2)	−0.0048 (13)	0.0181 (16)	−0.0141 (15)
C7	0.0527 (14)	0.0611 (15)	0.0817 (18)	0.0075 (11)	0.0069 (13)	−0.0092 (13)
C8	0.0620 (16)	0.0675 (17)	0.0832 (19)	0.0090 (12)	0.0001 (14)	−0.0080 (13)
C9	0.0547 (14)	0.0812 (18)	0.0564 (14)	0.0074 (12)	−0.0012 (11)	−0.0058 (13)
C10	0.0631 (16)	0.0620 (15)	0.0801 (18)	−0.0022 (12)	0.0071 (13)	−0.0053 (13)
C11	0.0472 (12)	0.0573 (13)	0.0547 (14)	0.0125 (11)	0.0051 (11)	0.0116 (11)
C12	0.0494 (13)	0.0596 (15)	0.0569 (13)	0.0076 (11)	0.0099 (11)	0.0148 (11)
C13	0.0443 (12)	0.0547 (13)	0.0534 (13)	0.0052 (10)	0.0043 (10)	0.0054 (10)
C14	0.0466 (13)	0.0711 (16)	0.0537 (14)	0.0062 (12)	0.0028 (10)	0.0120 (12)
C15	0.0421 (14)	0.109 (2)	0.108 (2)	−0.0052 (14)	0.0032 (14)	0.0201 (19)
C16	0.0726 (19)	0.103 (2)	0.112 (2)	−0.0251 (17)	0.0151 (18)	0.000 (2)
C17	0.0427 (11)	0.0522 (12)	0.0526 (13)	0.0089 (9)	0.0042 (10)	0.0051 (10)
C18	0.0460 (13)	0.0753 (18)	0.0690 (16)	0.0089 (12)	0.0075 (12)	−0.0097 (14)
C19	0.088 (4)	0.063 (3)	0.082 (3)	0.002 (3)	0.042 (3)	−0.005 (2)
C20	0.107 (5)	0.092 (5)	0.147 (7)	−0.016 (4)	0.074 (5)	−0.006 (4)
C19'	0.058 (5)	0.051 (5)	0.062 (6)	0.005 (4)	0.023 (4)	0.003 (4)
C20'	0.054 (5)	0.083 (8)	0.081 (7)	0.006 (5)	0.024 (5)	0.008 (5)
C21	0.0537 (14)	0.0630 (15)	0.0757 (16)	−0.0016 (11)	0.0039 (12)	0.0042 (12)
C22	0.0504 (13)	0.0806 (17)	0.0541 (14)	0.0083 (12)	−0.0002 (11)	0.0026 (12)
C23	0.051 (2)	0.086 (3)	0.064 (3)	−0.009 (2)	−0.003 (2)	−0.011 (2)
C24	0.052 (3)	0.069 (4)	0.079 (4)	−0.005 (3)	−0.006 (3)	−0.019 (3)
C25	0.081 (4)	0.062 (4)	0.116 (5)	−0.013 (3)	0.010 (3)	0.008 (3)
C26	0.061 (4)	0.086 (4)	0.118 (5)	−0.022 (3)	0.022 (4)	0.008 (4)
C27	0.044 (3)	0.123 (5)	0.115 (5)	0.006 (4)	0.010 (3)	0.030 (4)
C28	0.091 (4)	0.126 (5)	0.077 (4)	−0.013 (4)	−0.006 (3)	0.020 (4)
C29	0.070 (4)	0.101 (5)	0.097 (6)	−0.027 (3)	−0.010 (3)	0.006 (4)
C30	0.073 (4)	0.171 (8)	0.123 (6)	−0.026 (5)	0.022 (4)	0.038 (5)
C23'	0.058 (4)	0.071 (4)	0.078 (4)	0.005 (3)	0.003 (3)	−0.009 (3)
C24'	0.054 (5)	0.086 (6)	0.092 (7)	−0.006 (4)	0.011 (5)	−0.009 (5)
C25'	0.103 (7)	0.063 (7)	0.092 (6)	0.015 (6)	0.022 (5)	−0.009 (5)
C26'	0.078 (7)	0.103 (7)	0.134 (8)	−0.038 (5)	0.030 (6)	0.018 (6)
C27'	0.068 (7)	0.101 (6)	0.141 (9)	0.006 (5)	0.025 (6)	0.029 (7)
C28'	0.164 (10)	0.176 (10)	0.112 (8)	−0.041 (8)	0.041 (7)	0.022 (7)
C29'	0.146 (9)	0.190 (10)	0.130 (10)	−0.048 (7)	0.007 (8)	0.013 (7)
C30'	0.115 (9)	0.183 (13)	0.180 (13)	−0.014 (9)	0.046 (10)	0.047 (10)
N1	0.0574 (12)	0.0669 (13)	0.0720 (14)	0.0034 (10)	0.0072 (10)	−0.0115 (10)
N2	0.0476 (10)	0.0627 (11)	0.0476 (10)	0.0071 (9)	0.0038 (8)	0.0026 (9)
N3	0.0509 (11)	0.0518 (11)	0.0605 (12)	0.0033 (8)	0.0022 (9)	0.0026 (9)
N4	0.0488 (10)	0.0519 (11)	0.0562 (11)	0.0044 (8)	0.0074 (9)	0.0046 (9)
N5	0.0458 (10)	0.0585 (12)	0.0474 (10)	0.0066 (8)	0.0044 (8)	0.0039 (8)
N6	0.0459 (11)	0.0917 (16)	0.0773 (14)	0.0052 (11)	0.0064 (10)	0.0220 (12)
O1	0.0681 (11)	0.0774 (12)	0.0606 (10)	0.0014 (9)	0.0186 (9)	0.0169 (8)
O2	0.0665 (11)	0.0672 (11)	0.0858 (13)	0.0190 (9)	−0.0033 (9)	0.0195 (9)
O3	0.0558 (11)	0.0869 (14)	0.1120 (16)	0.0171 (10)	0.0110 (10)	0.0250 (11)
O4	0.0461 (9)	0.0742 (11)	0.0948 (13)	−0.0022 (8)	0.0045 (9)	0.0178 (9)
O5	0.0841 (14)	0.0743 (14)	0.1276 (18)	0.0186 (11)	0.0168 (12)	−0.0280 (12)
O6	0.0663 (11)	0.1049 (14)	0.0724 (12)	0.0029 (10)	0.0273 (10)	−0.0229 (11)

Geometric parameters (Å, º)

C1—C2	1.519 (4)	C20—H20A	0.9600
C1—H1A	0.9600	C20—H20B	0.9600
C1—H1B	0.9600	C20—H20C	0.9600
C1—H1C	0.9600	C19'—O6	1.464 (7)
C2—C4	1.353 (4)	C19'—C20'	1.499 (8)
C2—C3	1.377 (4)	C19'—H19C	0.9700
C3—C5	1.393 (4)	C19'—H19D	0.9700
C3—H3	0.9300	C20'—H20D	0.9600
C4—C6	1.374 (4)	C20'—H20E	0.9600
C4—H4	0.9300	C20'—H20F	0.9600
C5—C7	1.374 (4)	C21—N4	1.451 (3)
C5—H5	0.9300	C21—N6	1.461 (3)
C6—C7	1.381 (4)	C21—H21A	0.9700
C6—H6	0.9300	C21—H21B	0.9700
C7—C8	1.510 (4)	C22—N6	1.444 (3)
C8—N1	1.476 (3)	C22—N5	1.446 (3)
C8—H8A	0.9700	C22—H22A	0.9700
C8—H8B	0.9700	C22—H22B	0.9700
C9—N1	1.449 (3)	C23—N6	1.388 (4)
C9—N2	1.458 (3)	C23—C24	1.535 (5)
C9—H9A	0.9700	C23—H23A	0.9700
C9—H9B	0.9700	C23—H23B	0.9700
C10—N3	1.462 (3)	C24—C25	1.389 (3)
C10—N1	1.464 (3)	C24—C29	1.389 (3)
C10—H10A	0.9700	C25—C26	1.389 (3)
C10—H10B	0.9700	C25—H25	0.9300
C11—O1	1.210 (2)	C26—C27	1.389 (3)
C11—N2	1.380 (3)	C26—H26	0.9300
C11—N4	1.381 (3)	C27—C28	1.389 (3)
C12—O2	1.211 (3)	C27—C30	1.540 (6)
C12—N5	1.379 (3)	C28—C29	1.389 (3)
C12—N3	1.387 (3)	C28—H28	0.9300
C13—N3	1.445 (3)	C29—H29	0.9300
C13—N2	1.453 (3)	C30—H30A	0.9600
C13—C14	1.541 (3)	C30—H30B	0.9600
C13—C17	1.558 (3)	C30—H30C	0.9600
C14—O3	1.208 (3)	C23'—N6	1.283 (6)
C14—O4	1.296 (3)	C23'—C24'	1.527 (7)
C15—C16	1.458 (4)	C23'—H23C	0.9700
C15—O4	1.469 (3)	C23'—H23D	0.9700
C15—H15A	0.9700	C24'—C25'	1.386 (5)
C15—H15B	0.9700	C24'—C29'	1.386 (5)
C16—H16A	0.9600	C25'—C26'	1.386 (5)
C16—H16B	0.9600	C25'—H25'	0.9300
C16—H16C	0.9600	C26'—C27'	1.386 (5)
C17—N4	1.437 (3)	C26'—H26'	0.9300
C17—N5	1.458 (3)	C27'—C28'	1.386 (5)
C17—C18	1.541 (3)	C27'—C30'	1.542 (8)
C18—O5	1.201 (3)	C28'—C29'	1.386 (5)
C18—O6	1.305 (3)	C28'—H28'	0.9300
C19—C20	1.444 (5)	C29'—H29'	0.9300
C19—O6	1.487 (4)	C30'—H30D	0.9600
C19—H19A	0.9700	C30'—H30E	0.9600
C19—H19B	0.9700	C30'—H30F	0.9600
C2—C1—H1A	109.5	H20D—C20'—H20F	109.5
C2—C1—H1B	109.5	H20E—C20'—H20F	109.5
H1A—C1—H1B	109.5	N4—C21—N6	109.94 (19)
C2—C1—H1C	109.5	N4—C21—H21A	109.7
H1A—C1—H1C	109.5	N6—C21—H21A	109.7
H1B—C1—H1C	109.5	N4—C21—H21B	109.7
C4—C2—C3	117.7 (3)	N6—C21—H21B	109.7
C4—C2—C1	122.0 (3)	H21A—C21—H21B	108.2
C3—C2—C1	120.3 (3)	N6—C22—N5	110.89 (18)
C2—C3—C5	121.0 (3)	N6—C22—H22A	109.5
C2—C3—H3	119.5	N5—C22—H22A	109.5
C5—C3—H3	119.5	N6—C22—H22B	109.5
C2—C4—C6	121.7 (3)	N5—C22—H22B	109.5
C2—C4—H4	119.1	H22A—C22—H22B	108.0
C6—C4—H4	119.1	N6—C23—C24	115.7 (3)
C7—C5—C3	121.1 (3)	N6—C23—H23A	108.4
C7—C5—H5	119.5	C24—C23—H23A	108.4
C3—C5—H5	119.5	N6—C23—H23B	108.4
C4—C6—C7	121.7 (3)	C24—C23—H23B	108.4
C4—C6—H6	119.2	H23A—C23—H23B	107.4
C7—C6—H6	119.2	C25—C24—C29	120.0
C5—C7—C6	116.8 (3)	C25—C24—C23	120.4 (4)
C5—C7—C8	122.2 (2)	C29—C24—C23	119.6 (4)
C6—C7—C8	121.0 (2)	C24—C25—C26	120.0
N1—C8—C7	110.9 (2)	C24—C25—H25	120.0
N1—C8—H8A	109.5	C26—C25—H25	120.0
C7—C8—H8A	109.5	C25—C26—C27	120.0
N1—C8—H8B	109.5	C25—C26—H26	120.0
C7—C8—H8B	109.5	C27—C26—H26	120.0
H8A—C8—H8B	108.1	C28—C27—C26	120.0
N1—C9—N2	113.51 (19)	C28—C27—C30	120.4 (3)
N1—C9—H9A	108.9	C26—C27—C30	119.3 (3)
N2—C9—H9A	108.9	C27—C28—C29	120.0
N1—C9—H9B	108.9	C27—C28—H28	120.0
N2—C9—H9B	108.9	C29—C28—H28	120.0
H9A—C9—H9B	107.7	C28—C29—C24	120.0
N3—C10—N1	113.6 (2)	C28—C29—H29	120.0
N3—C10—H10A	108.9	C24—C29—H29	120.0
N1—C10—H10A	108.9	N6—C23'—C24'	118.3 (6)
N3—C10—H10B	108.9	N6—C23'—H23C	107.7
N1—C10—H10B	108.9	C24'—C23'—H23C	107.7
H10A—C10—H10B	107.7	N6—C23'—H23D	107.7
O1—C11—N2	126.1 (2)	C24'—C23'—H23D	107.7
O1—C11—N4	126.0 (2)	H23C—C23'—H23D	107.1
N2—C11—N4	107.92 (18)	C25'—C24'—C29'	120.0
O2—C12—N5	125.8 (2)	C25'—C24'—C23'	121.2 (7)
O2—C12—N3	125.6 (2)	C29'—C24'—C23'	118.5 (7)
N5—C12—N3	108.52 (18)	C24'—C25'—C26'	120.0
N3—C13—N2	111.30 (17)	C24'—C25'—H25'	120.0
N3—C13—C14	115.01 (18)	C26'—C25'—H25'	120.0
N2—C13—C14	108.99 (17)	C25'—C26'—C27'	120.0
N3—C13—C17	104.39 (17)	C25'—C26'—H26'	120.0
N2—C13—C17	102.95 (17)	C27'—C26'—H26'	120.0
C14—C13—C17	113.54 (18)	C28'—C27'—C26'	120.0
O3—C14—O4	126.1 (2)	C28'—C27'—C30'	120.0 (4)
O3—C14—C13	119.9 (2)	C26'—C27'—C30'	119.9 (4)
O4—C14—C13	114.0 (2)	C29'—C28'—C27'	120.0
C16—C15—O4	109.0 (2)	C29'—C28'—H28'	120.0
C16—C15—H15A	109.9	C27'—C28'—H28'	120.0
O4—C15—H15A	109.9	C28'—C29'—C24'	120.0
C16—C15—H15B	109.9	C28'—C29'—H29'	120.0
O4—C15—H15B	109.9	C24'—C29'—H29'	120.0
H15A—C15—H15B	108.3	C27'—C30'—H30D	109.5
C15—C16—H16A	109.5	C27'—C30'—H30E	109.5
C15—C16—H16B	109.5	H30D—C30'—H30E	109.5
H16A—C16—H16B	109.5	C27'—C30'—H30F	109.5
C15—C16—H16C	109.5	H30D—C30'—H30F	109.5
H16A—C16—H16C	109.5	H30E—C30'—H30F	109.5
H16B—C16—H16C	109.5	C9—N1—C10	110.11 (18)
N4—C17—N5	111.84 (16)	C9—N1—C8	112.9 (2)
N4—C17—C18	110.73 (19)	C10—N1—C8	114.4 (2)
N5—C17—C18	110.91 (18)	C11—N2—C13	111.53 (18)
N4—C17—C13	104.02 (17)	C11—N2—C9	123.04 (19)
N5—C17—C13	102.99 (17)	C13—N2—C9	116.41 (19)
C18—C17—C13	116.00 (18)	C12—N3—C13	110.27 (18)
O5—C18—O6	125.4 (2)	C12—N3—C10	120.69 (19)
O5—C18—C17	124.7 (2)	C13—N3—C10	116.11 (18)
O6—C18—C17	109.8 (2)	C11—N4—C17	111.25 (18)
C20—C19—O6	105.3 (4)	C11—N4—C21	120.93 (18)
C20—C19—H19A	110.7	C17—N4—C21	115.55 (18)
O6—C19—H19A	110.7	C12—N5—C22	121.67 (19)
C20—C19—H19B	110.7	C12—N5—C17	111.08 (18)
O6—C19—H19B	110.7	C22—N5—C17	116.44 (18)
H19A—C19—H19B	108.8	C23'—N6—C23	63.6 (3)
O6—C19'—C20'	103.6 (7)	C23'—N6—C22	125.3 (3)
O6—C19'—H19C	111.0	C23—N6—C22	114.0 (2)
C20'—C19'—H19C	111.0	C23'—N6—C21	119.8 (4)
O6—C19'—H19D	111.0	C23—N6—C21	115.2 (3)
C20'—C19'—H19D	111.0	C22—N6—C21	110.10 (19)
H19C—C19'—H19D	109.0	C14—O4—C15	116.7 (2)
C19'—C20'—H20D	109.5	C18—O6—C19'	135.9 (5)
C19'—C20'—H20E	109.5	C18—O6—C19	109.3 (3)
H20D—C20'—H20E	109.5	C19'—O6—C19	30.5 (3)
C19'—C20'—H20F	109.5
C4—C2—C3—C5	−0.6 (5)	N3—C13—N2—C11	104.7 (2)
C1—C2—C3—C5	179.8 (3)	C14—C13—N2—C11	−127.48 (19)
C3—C2—C4—C6	0.3 (5)	C17—C13—N2—C11	−6.6 (2)
C1—C2—C4—C6	179.9 (3)	N3—C13—N2—C9	−43.6 (2)
C2—C3—C5—C7	1.1 (4)	C14—C13—N2—C9	84.3 (2)
C2—C4—C6—C7	−0.6 (5)	C17—C13—N2—C9	−154.89 (17)
C3—C5—C7—C6	−1.3 (4)	N1—C9—N2—C11	−94.5 (3)
C3—C5—C7—C8	178.8 (2)	N1—C9—N2—C13	49.7 (3)
C4—C6—C7—C5	1.0 (4)	O2—C12—N3—C13	165.7 (2)
C4—C6—C7—C8	−179.0 (3)	N5—C12—N3—C13	−17.4 (2)
C5—C7—C8—N1	−109.7 (3)	O2—C12—N3—C10	25.8 (3)
C6—C7—C8—N1	70.4 (3)	N5—C12—N3—C10	−157.26 (19)
N3—C13—C14—O3	−175.5 (2)	N2—C13—N3—C12	−98.5 (2)
N2—C13—C14—O3	58.7 (3)	C14—C13—N3—C12	137.0 (2)
C17—C13—C14—O3	−55.4 (3)	C17—C13—N3—C12	11.9 (2)
N3—C13—C14—O4	2.5 (3)	N2—C13—N3—C10	43.4 (2)
N2—C13—C14—O4	−123.2 (2)	C14—C13—N3—C10	−81.2 (2)
C17—C13—C14—O4	122.7 (2)	C17—C13—N3—C10	153.78 (18)
N3—C13—C17—N4	−119.20 (17)	N1—C10—N3—C12	88.3 (3)
N2—C13—C17—N4	−2.86 (19)	N1—C10—N3—C13	−49.4 (3)
C14—C13—C17—N4	114.80 (19)	O1—C11—N4—C17	166.6 (2)
N3—C13—C17—N5	−2.4 (2)	N2—C11—N4—C17	−16.2 (2)
N2—C13—C17—N5	113.95 (16)	O1—C11—N4—C21	26.0 (3)
C14—C13—C17—N5	−128.39 (18)	N2—C11—N4—C21	−156.75 (18)
N3—C13—C17—C18	118.9 (2)	N5—C17—N4—C11	−98.9 (2)
N2—C13—C17—C18	−124.7 (2)	C18—C17—N4—C11	136.85 (18)
C14—C13—C17—C18	−7.1 (3)	C13—C17—N4—C11	11.6 (2)
N4—C17—C18—O5	1.9 (3)	N5—C17—N4—C21	44.0 (2)
N5—C17—C18—O5	−122.9 (3)	C18—C17—N4—C21	−80.3 (2)
C13—C17—C18—O5	120.1 (3)	C13—C17—N4—C21	154.43 (17)
N4—C17—C18—O6	−179.94 (18)	N6—C21—N4—C11	85.3 (2)
N5—C17—C18—O6	55.3 (2)	N6—C21—N4—C17	−53.7 (3)
C13—C17—C18—O6	−61.7 (3)	O2—C12—N5—C22	−24.3 (3)
N6—C23—C24—C25	−132.4 (4)	N3—C12—N5—C22	158.76 (18)
N6—C23—C24—C29	46.6 (5)	O2—C12—N5—C17	−167.3 (2)
C29—C24—C25—C26	0.0	N3—C12—N5—C17	15.8 (2)
C23—C24—C25—C26	179.0 (5)	N6—C22—N5—C12	−91.5 (2)
C24—C25—C26—C27	0.0	N6—C22—N5—C17	49.6 (3)
C25—C26—C27—C28	0.0	N4—C17—N5—C12	103.2 (2)
C25—C26—C27—C30	−173.4 (7)	C18—C17—N5—C12	−132.6 (2)
C26—C27—C28—C29	0.0	C13—C17—N5—C12	−7.9 (2)
C30—C27—C28—C29	173.3 (7)	N4—C17—N5—C22	−41.9 (2)
C27—C28—C29—C24	0.0	C18—C17—N5—C22	82.3 (2)
C25—C24—C29—C28	0.0	C13—C17—N5—C22	−152.99 (18)
C23—C24—C29—C28	−179.0 (5)	C24'—C23'—N6—C23	54.2 (6)
N6—C23'—C24'—C25'	−44.4 (10)	C24'—C23'—N6—C22	156.1 (5)
N6—C23'—C24'—C29'	130.0 (7)	C24'—C23'—N6—C21	−51.1 (8)
C29'—C24'—C25'—C26'	0.0	C24—C23—N6—C23'	−52.4 (5)
C23'—C24'—C25'—C26'	174.3 (8)	C24—C23—N6—C22	−171.4 (3)
C24'—C25'—C26'—C27'	0.0	C24—C23—N6—C21	59.9 (5)
C25'—C26'—C27'—C28'	0.0	N5—C22—N6—C23'	97.5 (4)
C25'—C26'—C27'—C30'	178.0 (12)	N5—C22—N6—C23	171.2 (3)
C26'—C27'—C28'—C29'	0.0	N5—C22—N6—C21	−57.5 (3)
C30'—C27'—C28'—C29'	−178.0 (12)	N4—C21—N6—C23'	−97.1 (4)
C27'—C28'—C29'—C24'	0.0	N4—C21—N6—C23	−169.9 (3)
C25'—C24'—C29'—C28'	0.0	N4—C21—N6—C22	59.5 (3)
C23'—C24'—C29'—C28'	−174.5 (8)	O3—C14—O4—C15	−4.0 (4)
N2—C9—N1—C10	−51.7 (3)	C13—C14—O4—C15	178.1 (2)
N2—C9—N1—C8	77.5 (3)	C16—C15—O4—C14	151.8 (3)
N3—C10—N1—C9	51.7 (3)	O5—C18—O6—C19'	12.1 (6)
N3—C10—N1—C8	−76.7 (3)	C17—C18—O6—C19'	−166.1 (5)
C7—C8—N1—C9	73.6 (3)	O5—C18—O6—C19	−5.9 (4)
C7—C8—N1—C10	−159.4 (2)	C17—C18—O6—C19	175.9 (3)
O1—C11—N2—C13	−168.7 (2)	C20'—C19'—O6—C18	−87.4 (9)
N4—C11—N2—C13	14.1 (2)	C20'—C19'—O6—C19	−52.3 (8)
O1—C11—N2—C9	−22.9 (3)	C20—C19—O6—C18	−159.9 (5)
N4—C11—N2—C9	159.90 (18)	C20—C19—O6—C19'	45.2 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22B···O1^i	0.97	2.40	3.356 (3)	169
C19—H19B···O3^i	0.97	2.47	3.179 (5)	129

Symmetry code: (i) x, −y+1/2, z−1/2.