Dieth­yl 2,6-dibenz­yl-4,8-dioxotetra­hydro-2,3a,4a,6,7a,8a-hexa­aza­cyclo­penta­[def]fluorene-8b,8c-dicarboxyl­ate

The mol­ecule of the title compound, C₂₈H₃₂N₆O₆, shows normal geometrical parameters. The crystal packing is stabilized by a C—H...O inter­action.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in main residue
• R factor = 0.072
• wR factor = 0.204
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.60 Ratio

Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.759
            Test value =      0.600
DIFMX02_ALERT_1_C  The minimum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       0.76 e/A   3
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.04 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C25
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C27
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C22
PLAT301_ALERT_3_C Main Residue  Disorder .........................       5.00 Perc.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C23    -C28           1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  12 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
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); 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.

2,6-Dibenzyl-4,8-dioxo-tetrahydro-2,3a,4a,6,7a,8a-hexaaza-cyclopenta[def] fluorene-8 b,8c-dicarboxylic acid diethyl ester

Crystal data

C28H32N6O6	Z = 2
Mr = 548.60	F(000) = 580
Triclinic, P1	Dx = 1.339 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6177 (6) Å	Cell parameters from 4320 reflections
b = 12.2882 (9) Å	θ = 2.7–26.4°
c = 14.9197 (11) Å	µ = 0.10 mm^−1
α = 95.008 (1)°	T = 292 K
β = 101.415 (1)°	Block, colorless
γ = 92.755 (1)°	0.30 × 0.20 × 0.20 mm
V = 1360.69 (18) Å^3

Data collection

Bruker SMART CCD diffractometer	4689 independent reflections
Radiation source: fine-focus sealed tube	3734 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω and φ scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
Tmin = 0.972, Tmax = 0.981	k = −14→13
9666 measured 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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.204	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.1005P)^2 + 1.0611P] where P = (Fo^2 + 2Fc^2)/3
4689 reflections	(Δ/σ)max = 0.002
359 parameters	Δρmax = 0.76 e Å^−3
14 restraints	Δρmin = −0.42 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	−0.0943 (6)	0.6194 (3)	−0.1051 (3)	0.0821 (12)
H1	0.0222	0.6322	−0.1138	0.099*
C2	−0.2342 (7)	0.5842 (4)	−0.1814 (3)	0.0920 (14)
H2	−0.2112	0.5737	−0.2404	0.110*
C3	−0.4033 (7)	0.5661 (4)	−0.1662 (4)	0.0945 (15)
H3	−0.4975	0.5422	−0.2149	0.113*
C4	−0.4334 (7)	0.5831 (4)	−0.0799 (4)	0.1072 (16)
H4	−0.5495	0.5709	−0.0705	0.129*
C5	−0.3001 (6)	0.6176 (4)	−0.0062 (3)	0.0891 (13)
H5	−0.3260	0.6292	0.0521	0.107*
C6	−0.1303 (5)	0.6347 (3)	−0.0181 (2)	0.0642 (9)
C7	0.0193 (5)	0.6695 (3)	0.0649 (2)	0.0634 (9)
H7A	−0.0333	0.6845	0.1184	0.076*
H7B	0.0959	0.6092	0.0761	0.076*
C8	0.2878 (4)	0.7873 (3)	0.1252 (2)	0.0502 (7)
H8A	0.3737	0.8322	0.1020	0.060*
H8B	0.3412	0.7190	0.1388	0.060*
C9	0.0317 (4)	0.8614 (2)	0.03958 (18)	0.0447 (7)
H9A	−0.0809	0.8420	−0.0035	0.054*
H9B	0.1021	0.9119	0.0121	0.054*
C10	−0.1640 (3)	0.8962 (2)	0.15436 (18)	0.0408 (6)
C11	0.2147 (3)	0.7853 (2)	0.28057 (19)	0.0422 (6)
C12	0.1466 (3)	0.9374 (2)	0.20090 (18)	0.0377 (6)
C13	0.2473 (4)	1.0457 (2)	0.19003 (19)	0.0476 (5)
C14	0.5397 (10)	1.1343 (6)	0.2004 (5)	0.091 (2)	0.657 (6)
H14A	0.4803	1.1999	0.2144	0.109*	0.657 (6)
H14B	0.6419	1.1281	0.2496	0.109*	0.657 (6)
C15	0.5946 (11)	1.1350 (6)	0.1105 (5)	0.0940 (19)	0.657 (6)
H15A	0.6547	1.0699	0.0990	0.141*	0.657 (6)
H15B	0.6744	1.1982	0.1116	0.141*	0.657 (6)
H15C	0.4903	1.1374	0.0628	0.141*	0.657 (6)
C16	0.0558 (3)	0.9435 (2)	0.28596 (18)	0.0389 (6)
C17	0.1019 (4)	1.0491 (2)	0.3524 (2)	0.0476 (5)
C18	0.3435 (5)	1.1665 (3)	0.4375 (3)	0.0686 (10)
H18A	0.3270	1.2273	0.4001	0.082*
H18B	0.2774	1.1781	0.4864	0.082*
C19	0.5332 (6)	1.1602 (4)	0.4762 (3)	0.0957 (14)
H19A	0.5477	1.1035	0.5169	0.144*
H19B	0.5807	1.2291	0.5098	0.144*
H19C	0.5965	1.1440	0.4276	0.144*
C20	−0.2471 (4)	0.8884 (3)	0.3078 (2)	0.0507 (7)
H20A	−0.2509	0.9453	0.3566	0.061*
H20B	−0.3685	0.8725	0.2727	0.061*
C21	0.0062 (4)	0.8060 (3)	0.3914 (2)	0.0514 (7)
H21A	0.0482	0.7362	0.4092	0.062*
H21B	0.0203	0.8558	0.4469	0.062*
C22	−0.2325 (4)	0.6909 (3)	0.2856 (2)	0.0558 (8)
H22A	−0.1584	0.6904	0.2397	0.067*
H22B	−0.3566	0.6918	0.2539	0.067*
C23	−0.2101 (5)	0.5876 (3)	0.3323 (2)	0.0605 (9)
C24	−0.1078 (7)	0.5094 (4)	0.3041 (5)	0.1110 (18)
H24	−0.0443	0.5239	0.2587	0.133*
C25	−0.0935 (10)	0.4105 (5)	0.3390 (5)	0.1365 (17)
H25	−0.0277	0.3573	0.3153	0.164*
C26	−0.1749 (9)	0.3913 (5)	0.4074 (5)	0.126 (2)
H26	−0.1584	0.3264	0.4349	0.152*
C27	−0.2819 (10)	0.4653 (5)	0.4375 (5)	0.1365 (17)
H27	−0.3408	0.4501	0.4844	0.164*
C28	−0.3045 (9)	0.5664 (4)	0.3977 (3)	0.1105 (18)
H28	−0.3817	0.6163	0.4160	0.133*
C14'	0.4697 (18)	1.1383 (12)	0.1335 (11)	0.091 (2)	0.343 (6)
H14C	0.4949	1.1156	0.0737	0.109*	0.343 (6)
H14D	0.3804	1.1924	0.1278	0.109*	0.343 (6)
C15'	0.6365 (18)	1.1771 (11)	0.2032 (10)	0.0940 (19)	0.343 (6)
H15D	0.6039	1.2080	0.2585	0.141*	0.343 (6)
H15E	0.7033	1.2318	0.1791	0.141*	0.343 (6)
H15F	0.7088	1.1165	0.2166	0.141*	0.343 (6)
N1	0.1270 (3)	0.7640 (2)	0.05421 (18)	0.0525 (6)
N2	−0.0060 (3)	0.91654 (18)	0.12427 (14)	0.0387 (5)
N3	0.2545 (3)	0.84417 (18)	0.21138 (15)	0.0392 (5)
N4	−0.1339 (3)	0.92994 (18)	0.24737 (15)	0.0405 (5)
N5	0.1182 (3)	0.84929 (18)	0.33161 (15)	0.0414 (5)
N6	−0.1848 (3)	0.7908 (2)	0.34832 (16)	0.0512 (6)
O1	−0.3045 (3)	0.85985 (19)	0.10672 (14)	0.0564 (6)
O2	0.2626 (3)	0.69531 (17)	0.29667 (15)	0.0583 (6)
O3	0.1732 (4)	1.12802 (19)	0.18676 (19)	0.0740 (7)
O4	0.4137 (4)	1.0353 (2)	0.1858 (3)	0.1027 (12)
O5	−0.0072 (3)	1.1066 (2)	0.37490 (18)	0.0745 (7)
O6	0.2776 (3)	1.06396 (17)	0.38139 (14)	0.0550 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.065 (2)	0.065 (2)	0.112 (3)	0.0057 (19)	0.010 (2)	0.000 (2)
C2	0.112 (4)	0.080 (3)	0.074 (3)	0.013 (3)	0.000 (2)	−0.012 (2)
C3	0.088 (3)	0.072 (3)	0.099 (4)	−0.011 (2)	−0.029 (3)	−0.010 (2)
C4	0.083 (3)	0.096 (4)	0.130 (5)	−0.029 (3)	0.001 (3)	0.008 (3)
C5	0.082 (3)	0.088 (3)	0.089 (3)	−0.020 (2)	0.005 (2)	0.005 (2)
C6	0.081 (3)	0.0390 (17)	0.062 (2)	−0.0016 (16)	−0.0070 (18)	−0.0041 (14)
C7	0.065 (2)	0.059 (2)	0.062 (2)	−0.0012 (16)	0.0076 (16)	0.0049 (16)
C8	0.0367 (15)	0.0535 (18)	0.0567 (17)	0.0044 (13)	0.0054 (13)	−0.0056 (14)
C9	0.0444 (15)	0.0468 (16)	0.0394 (14)	−0.0012 (12)	0.0031 (12)	−0.0002 (12)
C10	0.0355 (14)	0.0399 (14)	0.0440 (14)	0.0073 (11)	0.0002 (11)	0.0028 (11)
C11	0.0318 (13)	0.0398 (15)	0.0480 (15)	−0.0019 (11)	−0.0074 (11)	0.0033 (12)
C12	0.0339 (13)	0.0348 (13)	0.0410 (14)	−0.0015 (10)	0.0009 (11)	0.0015 (11)
C13	0.0499 (12)	0.0443 (12)	0.0453 (11)	−0.0042 (9)	0.0047 (9)	0.0012 (9)
C14	0.078 (4)	0.088 (4)	0.110 (5)	−0.037 (4)	0.031 (4)	0.019 (5)
C15	0.109 (5)	0.070 (4)	0.115 (5)	0.007 (3)	0.038 (4)	0.038 (4)
C16	0.0344 (13)	0.0385 (14)	0.0404 (14)	0.0000 (11)	0.0000 (11)	0.0028 (11)
C17	0.0499 (12)	0.0443 (12)	0.0453 (11)	−0.0042 (9)	0.0047 (9)	0.0012 (9)
C18	0.071 (2)	0.059 (2)	0.064 (2)	−0.0137 (17)	0.0001 (17)	−0.0186 (16)
C19	0.078 (3)	0.076 (3)	0.109 (3)	−0.023 (2)	−0.021 (2)	−0.014 (2)
C20	0.0402 (16)	0.0619 (19)	0.0492 (16)	0.0006 (13)	0.0104 (13)	−0.0007 (14)
C21	0.0530 (17)	0.0582 (18)	0.0400 (15)	−0.0064 (14)	0.0027 (13)	0.0083 (13)
C22	0.0545 (18)	0.061 (2)	0.0474 (16)	−0.0087 (15)	0.0039 (14)	0.0048 (14)
C23	0.0967 (19)	0.090 (2)	0.0979 (19)	−0.0178 (16)	−0.0018 (15)	0.0085 (15)
C24	0.096 (3)	0.090 (3)	0.168 (5)	0.022 (3)	0.055 (4)	0.059 (3)
C25	0.168 (5)	0.099 (3)	0.158 (4)	−0.012 (3)	0.061 (4)	0.051 (3)
C26	0.132 (5)	0.096 (4)	0.141 (5)	−0.009 (4)	−0.013 (4)	0.064 (4)
C27	0.168 (5)	0.099 (3)	0.158 (4)	−0.012 (3)	0.061 (4)	0.051 (3)
C28	0.173 (5)	0.072 (3)	0.098 (3)	−0.025 (3)	0.062 (4)	0.010 (2)
C14'	0.078 (4)	0.088 (4)	0.110 (5)	−0.037 (4)	0.031 (4)	0.019 (5)
C15'	0.109 (5)	0.070 (4)	0.115 (5)	0.007 (3)	0.038 (4)	0.038 (4)
N1	0.0468 (14)	0.0444 (14)	0.0583 (15)	0.0010 (11)	−0.0026 (11)	−0.0072 (11)
N2	0.0353 (12)	0.0405 (12)	0.0371 (11)	0.0015 (9)	0.0003 (9)	0.0031 (9)
N3	0.0301 (11)	0.0396 (12)	0.0449 (12)	0.0013 (9)	0.0015 (9)	0.0014 (10)
N4	0.0335 (12)	0.0446 (13)	0.0415 (12)	0.0024 (9)	0.0032 (9)	0.0033 (10)
N5	0.0382 (12)	0.0432 (13)	0.0396 (12)	−0.0004 (10)	−0.0003 (9)	0.0068 (10)
N6	0.0450 (14)	0.0621 (16)	0.0447 (13)	−0.0062 (12)	0.0069 (11)	0.0062 (12)
O1	0.0318 (11)	0.0740 (15)	0.0558 (12)	0.0017 (10)	−0.0047 (9)	−0.0044 (10)
O2	0.0573 (13)	0.0448 (12)	0.0695 (14)	0.0121 (10)	−0.0007 (11)	0.0140 (10)
O3	0.0782 (17)	0.0416 (13)	0.0966 (19)	−0.0021 (12)	0.0015 (14)	0.0159 (12)
O4	0.0722 (18)	0.0540 (15)	0.155 (4)	−0.0157 (13)	0.071 (2)	−0.0018 (18)
O5	0.0609 (15)	0.0684 (16)	0.0875 (18)	0.0064 (12)	0.0142 (13)	−0.0290 (13)
O6	0.0486 (12)	0.0517 (12)	0.0552 (12)	−0.0060 (9)	−0.0029 (9)	−0.0112 (10)

Geometric parameters (Å, º)

C1—C6	1.378 (6)	C16—N4	1.442 (3)
C1—C2	1.417 (6)	C16—N5	1.446 (3)
C1—H1	0.9300	C16—C17	1.545 (4)
C2—C3	1.363 (7)	C17—O5	1.195 (4)
C2—H2	0.9300	C17—O6	1.320 (4)
C3—C4	1.352 (7)	C18—C19	1.455 (6)
C3—H3	0.9300	C18—O6	1.459 (4)
C4—C5	1.362 (7)	C18—H18A	0.9700
C4—H4	0.9300	C18—H18B	0.9700
C5—C6	1.350 (6)	C19—H19A	0.9600
C5—H5	0.9300	C19—H19B	0.9600
C6—C7	1.522 (5)	C19—H19C	0.9600
C7—N1	1.428 (4)	C20—N6	1.449 (4)
C7—H7A	0.9700	C20—N4	1.470 (4)
C7—H7B	0.9700	C20—H20A	0.9700
C8—N1	1.451 (4)	C20—H20B	0.9700
C8—N3	1.482 (4)	C21—N6	1.465 (4)
C8—H8A	0.9700	C21—N5	1.466 (4)
C8—H8B	0.9700	C21—H21A	0.9700
C9—N1	1.440 (4)	C21—H21B	0.9700
C9—N2	1.467 (3)	C22—N6	1.462 (4)
C9—H9A	0.9700	C22—C23	1.502 (5)
C9—H9B	0.9700	C22—H22A	0.9700
C10—O1	1.203 (3)	C22—H22B	0.9700
C10—N4	1.384 (3)	C23—C24	1.356 (6)
C10—N2	1.385 (4)	C23—C28	1.357 (6)
C11—O2	1.210 (3)	C24—C25	1.365 (7)
C11—N5	1.382 (4)	C24—H24	0.9300
C11—N3	1.383 (4)	C25—C26	1.326 (9)
C12—N3	1.443 (3)	C25—H25	0.9300
C12—N2	1.455 (3)	C26—C27	1.356 (9)
C12—C13	1.541 (4)	C26—H26	0.9300
C12—C16	1.559 (4)	C27—C28	1.427 (8)
C13—O3	1.182 (4)	C27—H27	0.9300
C13—O4	1.293 (4)	C28—H28	0.9300
C14—C15	1.483 (7)	C14'—C15'	1.502 (10)
C14—O4	1.486 (7)	C14'—O4	1.627 (14)
C14—H14A	0.9700	C14'—H14C	0.9700
C14—H14B	0.9700	C14'—H14D	0.9700
C15—H15A	0.9600	C15'—H15D	0.9600
C15—H15B	0.9600	C15'—H15E	0.9600
C15—H15C	0.9600	C15'—H15F	0.9600
C6—C1—C2	120.2 (4)	H19A—C19—H19B	109.5
C6—C1—H1	119.9	C18—C19—H19C	109.5
C2—C1—H1	119.9	H19A—C19—H19C	109.5
C3—C2—C1	118.4 (5)	H19B—C19—H19C	109.5
C3—C2—H2	120.8	N6—C20—N4	113.5 (2)
C1—C2—H2	120.8	N6—C20—H20A	108.9
C4—C3—C2	119.6 (4)	N4—C20—H20A	108.9
C4—C3—H3	120.2	N6—C20—H20B	108.9
C2—C3—H3	120.2	N4—C20—H20B	108.9
C3—C4—C5	122.5 (5)	H20A—C20—H20B	107.7
C3—C4—H4	118.7	N6—C21—N5	113.5 (2)
C5—C4—H4	118.7	N6—C21—H21A	108.9
C6—C5—C4	119.7 (5)	N5—C21—H21A	108.9
C6—C5—H5	120.2	N6—C21—H21B	108.9
C4—C5—H5	120.2	N5—C21—H21B	108.9
C5—C6—C1	119.6 (4)	H21A—C21—H21B	107.7
C5—C6—C7	119.5 (4)	N6—C22—C23	113.8 (3)
C1—C6—C7	120.9 (4)	N6—C22—H22A	108.8
N1—C7—C6	113.5 (3)	C23—C22—H22A	108.8
N1—C7—H7A	108.9	N6—C22—H22B	108.8
C6—C7—H7A	108.9	C23—C22—H22B	108.8
N1—C7—H7B	108.9	H22A—C22—H22B	107.7
C6—C7—H7B	108.9	C24—C23—C28	118.7 (4)
H7A—C7—H7B	107.7	C24—C23—C22	120.5 (4)
N1—C8—N3	113.5 (2)	C28—C23—C22	120.6 (4)
N1—C8—H8A	108.9	C23—C24—C25	123.1 (5)
N3—C8—H8A	108.9	C23—C24—H24	118.5
N1—C8—H8B	108.9	C25—C24—H24	118.5
N3—C8—H8B	108.9	C26—C25—C24	119.0 (7)
H8A—C8—H8B	107.7	C26—C25—H25	120.5
N1—C9—N2	113.3 (2)	C24—C25—H25	120.5
N1—C9—H9A	108.9	C25—C26—C27	120.6 (6)
N2—C9—H9A	108.9	C25—C26—H26	119.7
N1—C9—H9B	108.9	C27—C26—H26	119.7
N2—C9—H9B	108.9	C26—C27—C28	120.4 (6)
H9A—C9—H9B	107.7	C26—C27—H27	119.8
O1—C10—N4	126.2 (3)	C28—C27—H27	119.8
O1—C10—N2	125.6 (3)	C23—C28—C27	118.0 (5)
N4—C10—N2	108.1 (2)	C23—C28—H28	121.0
O2—C11—N5	125.5 (3)	C27—C28—H28	121.0
O2—C11—N3	126.2 (3)	C15'—C14'—O4	96.4 (10)
N5—C11—N3	108.2 (2)	C15'—C14'—H14C	112.5
N3—C12—N2	111.9 (2)	O4—C14'—H14C	112.5
N3—C12—C13	115.6 (2)	C15'—C14'—H14D	112.5
N2—C12—C13	108.1 (2)	O4—C14'—H14D	112.5
N3—C12—C16	104.3 (2)	H14C—C14'—H14D	110.0
N2—C12—C16	102.7 (2)	C14'—C15'—H15D	109.5
C13—C12—C16	113.5 (2)	C14'—C15'—H15E	109.5
O3—C13—O4	125.9 (3)	H15D—C15'—H15E	109.5
O3—C13—C12	120.7 (3)	C14'—C15'—H15F	109.5
O4—C13—C12	113.4 (3)	H15D—C15'—H15F	109.5
C15—C14—O4	102.4 (6)	H15E—C15'—H15F	109.5
C15—C14—H14A	111.3	C7—N1—C9	115.1 (3)
O4—C14—H14A	111.3	C7—N1—C8	114.3 (3)
C15—C14—H14B	111.3	C9—N1—C8	110.7 (2)
O4—C14—H14B	111.3	C10—N2—C12	111.4 (2)
H14A—C14—H14B	109.2	C10—N2—C9	123.0 (2)
N4—C16—N5	111.5 (2)	C12—N2—C9	115.8 (2)
N4—C16—C17	111.0 (2)	C11—N3—C12	110.7 (2)
N5—C16—C17	110.6 (2)	C11—N3—C8	120.7 (2)
N4—C16—C12	104.5 (2)	C12—N3—C8	115.9 (2)
N5—C16—C12	103.0 (2)	C10—N4—C16	110.7 (2)
C17—C16—C12	115.9 (2)	C10—N4—C20	122.4 (2)
O5—C17—O6	125.9 (3)	C16—N4—C20	115.6 (2)
O5—C17—C16	124.2 (3)	C11—N5—C16	111.8 (2)
O6—C17—C16	109.8 (2)	C11—N5—C21	124.0 (2)
C19—C18—O6	108.5 (3)	C16—N5—C21	116.2 (2)
C19—C18—H18A	110.0	C20—N6—C22	113.4 (2)
O6—C18—H18A	110.0	C20—N6—C21	110.9 (2)
C19—C18—H18B	110.0	C22—N6—C21	114.0 (3)
O6—C18—H18B	110.0	C13—O4—C14	119.4 (4)
H18A—C18—H18B	108.4	C13—O4—C14'	105.2 (6)
C18—C19—H19A	109.5	C17—O6—C18	116.3 (2)
C18—C19—H19B	109.5
C6—C1—C2—C3	0.0 (6)	C16—C12—N2—C9	−154.9 (2)
C1—C2—C3—C4	0.7 (7)	N1—C9—N2—C10	−92.6 (3)
C2—C3—C4—C5	−0.3 (8)	N1—C9—N2—C12	50.4 (3)
C3—C4—C5—C6	−0.7 (8)	O2—C11—N3—C12	168.5 (3)
C4—C5—C6—C1	1.4 (6)	N5—C11—N3—C12	−14.6 (3)
C4—C5—C6—C7	−178.0 (4)	O2—C11—N3—C8	28.3 (4)
C2—C1—C6—C5	−1.0 (6)	N5—C11—N3—C8	−154.8 (2)
C2—C1—C6—C7	178.3 (3)	N2—C12—N3—C11	−99.9 (2)
C5—C6—C7—N1	−128.9 (4)	C13—C12—N3—C11	135.7 (2)
C1—C6—C7—N1	51.8 (4)	C16—C12—N3—C11	10.4 (3)
N3—C12—C13—O3	−175.3 (3)	N2—C12—N3—C8	42.3 (3)
N2—C12—C13—O3	58.4 (3)	C13—C12—N3—C8	−82.1 (3)
C16—C12—C13—O3	−54.8 (4)	C16—C12—N3—C8	152.6 (2)
N3—C12—C13—O4	4.3 (4)	N1—C8—N3—C11	90.3 (3)
N2—C12—C13—O4	−122.0 (3)	N1—C8—N3—C12	−47.9 (3)
C16—C12—C13—O4	124.8 (3)	O1—C10—N4—C16	166.1 (3)
N3—C12—C16—N4	−119.1 (2)	N2—C10—N4—C16	−16.8 (3)
N2—C12—C16—N4	−2.2 (2)	O1—C10—N4—C20	24.2 (4)
C13—C12—C16—N4	114.3 (2)	N2—C10—N4—C20	−158.7 (2)
N3—C12—C16—N5	−2.5 (2)	N5—C16—N4—C10	−99.0 (2)
N2—C12—C16—N5	114.4 (2)	C17—C16—N4—C10	137.2 (2)
C13—C12—C16—N5	−129.2 (2)	C12—C16—N4—C10	11.5 (3)
N3—C12—C16—C17	118.4 (2)	N5—C16—N4—C20	45.7 (3)
N2—C12—C16—C17	−124.7 (2)	C17—C16—N4—C20	−78.2 (3)
C13—C12—C16—C17	−8.2 (3)	C12—C16—N4—C20	156.2 (2)
N4—C16—C17—O5	6.1 (4)	N6—C20—N4—C10	89.7 (3)
N5—C16—C17—O5	−118.2 (3)	N6—C20—N4—C16	−50.5 (3)
C12—C16—C17—O5	125.1 (3)	O2—C11—N5—C16	−170.1 (3)
N4—C16—C17—O6	−175.3 (2)	N3—C11—N5—C16	13.0 (3)
N5—C16—C17—O6	60.4 (3)	O2—C11—N5—C21	−22.6 (4)
C12—C16—C17—O6	−56.3 (3)	N3—C11—N5—C21	160.5 (2)
N6—C22—C23—C24	−125.3 (4)	N4—C16—N5—C11	105.4 (2)
N6—C22—C23—C28	60.7 (5)	C17—C16—N5—C11	−130.6 (2)
C28—C23—C24—C25	−0.7 (9)	C12—C16—N5—C11	−6.2 (3)
C22—C23—C24—C25	−174.8 (5)	N4—C16—N5—C21	−44.9 (3)
C23—C24—C25—C26	−3.9 (11)	C17—C16—N5—C21	79.1 (3)
C24—C25—C26—C27	5.0 (11)	C12—C16—N5—C21	−156.4 (2)
C25—C26—C27—C28	−1.7 (11)	N6—C21—N5—C11	−97.9 (3)
C24—C23—C28—C27	3.9 (8)	N6—C21—N5—C16	48.3 (3)
C22—C23—C28—C27	178.0 (5)	N4—C20—N6—C22	−79.0 (3)
C26—C27—C28—C23	−2.8 (9)	N4—C20—N6—C21	50.7 (3)
C6—C7—N1—C9	60.2 (4)	C23—C22—N6—C20	−165.7 (3)
C6—C7—N1—C8	−169.9 (3)	C23—C22—N6—C21	66.1 (3)
N2—C9—N1—C7	78.6 (3)	N5—C21—N6—C20	−49.7 (3)
N2—C9—N1—C8	−52.9 (3)	N5—C21—N6—C22	79.8 (3)
N3—C8—N1—C7	−80.3 (3)	O3—C13—O4—C14	15.9 (7)
N3—C8—N1—C9	51.7 (3)	C12—C13—O4—C14	−163.7 (4)
O1—C10—N2—C12	−167.5 (3)	O3—C13—O4—C14'	−23.3 (7)
N4—C10—N2—C12	15.4 (3)	C12—C13—O4—C14'	157.1 (6)
O1—C10—N2—C9	−23.2 (4)	C15—C14—O4—C13	−117.0 (6)
N4—C10—N2—C9	159.7 (2)	C15—C14—O4—C14'	−39.8 (10)
N3—C12—N2—C10	103.6 (2)	C15'—C14'—O4—C13	129.1 (9)
C13—C12—N2—C10	−128.0 (2)	C15'—C14'—O4—C14	10.7 (8)
C16—C12—N2—C10	−7.8 (3)	O5—C17—O6—C18	−7.4 (5)
N3—C12—N2—C9	−43.6 (3)	C16—C17—O6—C18	173.9 (3)
C13—C12—N2—C9	84.9 (3)	C19—C18—O6—C17	170.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1^i	0.97	2.44	3.261 (3)	142

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