Diethyl 5,10-dihydro-6-phenyl­ethynyl-4,11-dioxo-cis-1H,3H,4H,11H-2-oxa-3a,4a,10a,11a-tetra­aza­benz[f]­indeno[2,1,7-ija]azulene-11b,11c-dicarboxyl­ate

Chen, Y.-F.; Cui, Y.-F.

doi:10.1107/S1600536806040256

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Diethyl 5,10-dihydro-6-phenylethynyl-4,11-dioxo-cis-1H,3H,4H,11H-2-oxa-3a,4a,10a,11a-tetraazabenz[f]indeno[2,1,7-ija]azulene-11b,11c-dicarboxylate

Y.-F. Chen and Y.-F. Cui

The title compound, C₂₈H₂₆N₄O₇, (I) crystallizes with two molecules in the asymmetric unit. It is a glycoluril derivative with five fused rings. A phenylethynyl-substituted benzene ring is fused to a seven-membered ring, which binds two of the N atoms from separate rings of the glycoluril system. The other two N atoms are each linked to an O atom by methylene groups, forming a six-membered ring. The crystal structure is stabilized by intermolecular C—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806040256/sj2132sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806040256/sj2132Isup2.hkl Contains datablock I

CCDC reference: 628400

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.006 Å
Disorder in main residue
R factor = 0.049
wR factor = 0.146
Data-to-parameter ratio = 8.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        O13
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C53
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for       C53'

Alert level C
PLAT048_ALERT_1_C MoietyFormula Not Given ........................          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.07 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.31 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.74 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.65 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        O11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C48
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C52
PLAT301_ALERT_3_C Main Residue  Disorder .........................       2.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C49    -   C50    ...       1.36 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C34    -   C35    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C36    -   C37    ...       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C6     -   C7     ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C8     -   C9     ...       1.44 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          9
            C1  -C6  -C7  -C8      3.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         10
            C5  -C6  -C7  -C8     15.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         11
            C6  -C7  -C8  -C9     16.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         12
            C7  -C8  -C9  -C10    32.00  9.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         13
            C7  -C8  -C9  -C13  -149.00  9.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         61
            C29 -C34 -C35 -C36    41.00 16.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         62
            C33 -C34 -C35 -C36  -141.00 15.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         63
            C34 -C35 -C36 -C37   109.00 16.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         64
            C35 -C36 -C37 -C38    45.00  8.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         65
            C35 -C36 -C37 -C42  -134.00  8.00   1.555   1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      33.40 Deg.
              C53  -O13  -C53'    1.555   1.555   1.555

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.28
           From the CIF: _reflns_number_total               6494
           Count of symmetry unique reflns         6578
           Completeness (_total/calc)             98.72%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  14 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
  11 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

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 5,10-dihydro-6-phenylethynyl-4,11-dioxo-cis-1H,3H,4H,11H-2-oxa- 3a,4a,10a,11a-tetraazabenz[f]indeno[2,1,7-ija]azulene-11b,11c-dicarboxylate top

Crystal data top

C₂₈H₂₆N₄O₇	F(000) = 2224
M_r = 530.53	D_x = 1.352 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5345 reflections
a = 15.8491 (18) Å	θ = 2.2–22.4°
b = 9.4801 (11) Å	µ = 0.10 mm⁻¹
c = 34.707 (4) Å	T = 292 K
V = 5214.7 (10) Å³	Irregular fragment, colorless
Z = 8	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker CCD area detector diffractometer	4574 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.037
Graphite monochromator	θ_max = 28.3°, θ_min = 1.2°
φ and ω scans	h = −21→21
43854 measured reflections	k = −12→12
6494 independent reflections	l = −45→45

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.089P)² + 0.1756P] where P = (F_o² + 2F_c²)/3
6494 reflections	(Δ/σ)_max < 0.001
727 parameters	Δρ_max = 0.28 e Å⁻³
3 restraints	Δρ_min = −0.28 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.3585 (2)	0.4820 (4)	0.10948 (11)	0.0626 (9)
H1	0.3347	0.4108	0.1244	0.075*
C2	0.4290 (3)	0.4536 (5)	0.08742 (13)	0.0763 (12)
H2	0.4516	0.3630	0.0872	0.092*
C3	0.4651 (3)	0.5561 (6)	0.06625 (15)	0.0825 (12)
H3	0.5133	0.5367	0.0519	0.099*
C4	0.4308 (3)	0.6901 (6)	0.06580 (13)	0.0829 (13)
H4	0.4557	0.7602	0.0509	0.100*
C5	0.3600 (3)	0.7207 (4)	0.08728 (11)	0.0679 (10)
H5	0.3371	0.8110	0.0868	0.082*
C6	0.3229 (2)	0.6158 (4)	0.10966 (9)	0.0518 (7)
C7	0.2490 (2)	0.6457 (4)	0.13254 (10)	0.0554 (8)
C8	0.1881 (2)	0.6693 (4)	0.15130 (10)	0.0547 (8)
C9	0.1145 (2)	0.7040 (4)	0.17381 (9)	0.0506 (7)
C10	0.0674 (3)	0.8220 (4)	0.16327 (12)	0.0683 (10)
H10	0.0837	0.8757	0.1421	0.082*
C11	−0.0027 (3)	0.8592 (5)	0.18398 (14)	0.0757 (12)
H11	−0.0333	0.9391	0.1771	0.091*
C12	−0.0281 (2)	0.7788 (4)	0.21488 (12)	0.0624 (9)
H12	−0.0753	0.8056	0.2290	0.075*
C13	0.08895 (19)	0.6214 (3)	0.20518 (9)	0.0437 (7)
C14	0.0159 (2)	0.6584 (4)	0.22525 (10)	0.0505 (8)
C15	0.1393 (2)	0.4913 (4)	0.21609 (9)	0.0482 (7)
H15A	0.1050	0.4083	0.2114	0.058*
H15B	0.1886	0.4854	0.1996	0.058*
C16	−0.01914 (19)	0.5655 (4)	0.25694 (10)	0.0536 (8)
H16A	−0.0716	0.6064	0.2661	0.064*
H16B	−0.0323	0.4738	0.2461	0.064*
C17	0.23213 (19)	0.5726 (4)	0.26816 (10)	0.0481 (7)
C18	0.0402 (2)	0.6400 (4)	0.31935 (9)	0.0486 (7)
C19	0.11040 (18)	0.4553 (3)	0.28754 (9)	0.0429 (6)
C20	0.0859 (2)	0.2985 (4)	0.28595 (11)	0.0542 (8)
C21	0.0162 (4)	0.1124 (5)	0.31883 (17)	0.0951 (16)
H21A	0.0644	0.0554	0.3115	0.114*
H21B	0.0019	0.0906	0.3453	0.114*
C22	−0.0557 (4)	0.0796 (7)	0.2937 (3)	0.142 (3)
H22A	−0.1016	0.1422	0.2994	0.212*
H22B	−0.0732	−0.0161	0.2979	0.212*
H22C	−0.0392	0.0913	0.2672	0.212*
C23	0.16130 (19)	0.5001 (3)	0.32426 (9)	0.0456 (7)
C24	0.1864 (2)	0.3804 (4)	0.35169 (10)	0.0526 (8)
C25	0.2591 (3)	0.1596 (5)	0.35404 (14)	0.0758 (12)
H25A	0.2112	0.1029	0.3620	0.091*
H25B	0.2901	0.1876	0.3769	0.091*
C26	0.3139 (3)	0.0780 (5)	0.32800 (17)	0.0863 (14)
H26A	0.2845	0.0599	0.3043	0.130*
H26B	0.3286	−0.0099	0.3400	0.130*
H26C	0.3643	0.1309	0.3227	0.130*
C27	0.2743 (3)	0.6770 (5)	0.33098 (13)	0.0719 (11)
H27A	0.2999	0.6372	0.3539	0.086*
H27B	0.3183	0.7228	0.3161	0.086*
C28	0.1497 (3)	0.7138 (4)	0.36446 (11)	0.0643 (9)
H28A	0.1088	0.7843	0.3722	0.077*
H28B	0.1750	0.6746	0.3876	0.077*
C29	0.3731 (3)	0.9950 (5)	0.17015 (12)	0.0694 (11)
H29	0.3955	0.9250	0.1544	0.083*
C30	0.3028 (3)	0.9680 (6)	0.19195 (15)	0.0813 (12)
H30	0.2784	0.8788	0.1911	0.098*
C31	0.2683 (3)	1.0682 (6)	0.21465 (15)	0.0818 (13)
H31	0.2202	1.0482	0.2290	0.098*
C32	0.3037 (3)	1.1980 (5)	0.21647 (14)	0.0817 (13)
H32	0.2792	1.2670	0.2319	0.098*
C33	0.3767 (3)	1.2296 (4)	0.19555 (12)	0.0722 (11)
H33	0.4020	1.3178	0.1976	0.087*
C34	0.4108 (2)	1.1268 (4)	0.17154 (10)	0.0585 (9)
C35	0.4854 (3)	1.1561 (4)	0.14914 (10)	0.0620 (9)
C36	0.5464 (3)	1.1786 (4)	0.12983 (11)	0.0588 (9)
C37	0.6179 (2)	1.2128 (4)	0.10665 (10)	0.0555 (8)
C38	0.6640 (3)	1.3345 (5)	0.11505 (15)	0.0773 (12)
H38	0.6486	1.3901	0.1360	0.093*
C39	0.7307 (4)	1.3723 (5)	0.09303 (18)	0.0885 (14)
H39	0.7599	1.4550	0.0986	0.106*
C40	0.7561 (3)	1.2891 (5)	0.06228 (14)	0.0714 (11)
H40	0.8019	1.3166	0.0474	0.086*
C41	0.7133 (2)	1.1644 (4)	0.05349 (10)	0.0522 (8)
C42	0.6421 (2)	1.1266 (3)	0.07533 (9)	0.0475 (7)
C43	0.5946 (2)	0.9917 (3)	0.06761 (9)	0.0476 (7)
H43A	0.6302	0.9128	0.0748	0.057*
H43B	0.5453	0.9894	0.0842	0.057*
C44	0.7496 (2)	1.0688 (4)	0.02315 (11)	0.0569 (8)
H44A	0.7986	1.1147	0.0120	0.068*
H44B	0.7690	0.9831	0.0356	0.068*
C45	0.4995 (2)	1.0449 (4)	0.01316 (10)	0.0509 (8)
C46	0.6887 (2)	1.0968 (4)	−0.04224 (11)	0.0571 (8)
C47	0.62469 (19)	0.9301 (3)	−0.00215 (9)	0.0463 (7)
C48	0.6607 (3)	0.7819 (4)	0.00525 (11)	0.0629 (10)
C49	0.7683 (6)	0.6139 (8)	−0.0162 (3)	0.137 (3)
H49A	0.8216	0.6173	−0.0299	0.164*
H49B	0.7781	0.5936	0.0109	0.164*
C50	0.7127 (5)	0.5225 (10)	−0.0325 (3)	0.142 (3)
H50A	0.6633	0.5154	−0.0166	0.213*
H50B	0.7385	0.4313	−0.0349	0.213*
H50C	0.6970	0.5563	−0.0576	0.213*
C51	0.5721 (2)	0.9474 (4)	−0.03957 (10)	0.0527 (8)
C52	0.5476 (3)	0.8106 (5)	−0.06107 (14)	0.0775 (12)
C53	0.4911 (6)	0.5718 (10)	−0.0481 (4)	0.078 (3)	0.568 (19)
H53A	0.5251	0.5403	−0.0697	0.094*	0.568 (19)
H53B	0.5007	0.5103	−0.0262	0.094*	0.568 (19)
C54	0.4002 (8)	0.5797 (18)	−0.0583 (6)	0.108 (5)	0.568 (19)
H54A	0.3682	0.6068	−0.0360	0.162*	0.568 (19)
H54B	0.3813	0.4891	−0.0672	0.162*	0.568 (19)
H54C	0.3923	0.6483	−0.0783	0.162*	0.568 (19)
C53'	0.4658 (11)	0.6190 (15)	−0.0669 (4)	0.081 (4)	0.432 (19)
H53C	0.4304	0.6674	−0.0855	0.098*	0.432 (19)
H53D	0.5071	0.5619	−0.0804	0.098*	0.432 (19)
C54'	0.4147 (19)	0.533 (2)	−0.0392 (6)	0.127 (9)	0.432 (19)
H54D	0.4382	0.5415	−0.0139	0.191*	0.432 (19)
H54E	0.4156	0.4360	−0.0471	0.191*	0.432 (19)
H54F	0.3576	0.5667	−0.0391	0.191*	0.432 (19)
C55	0.4539 (3)	1.1111 (5)	−0.05294 (13)	0.0768 (12)
H55A	0.4267	1.0561	−0.0729	0.092*
H55B	0.4107	1.1645	−0.0395	0.092*
C56	0.5756 (3)	1.1277 (5)	−0.09011 (12)	0.0799 (12)
H56A	0.6139	1.1929	−0.1027	0.096*
H56B	0.5492	1.0703	−0.1099	0.096*
N1	0.16663 (15)	0.4902 (3)	0.25618 (7)	0.0433 (6)
N2	0.03689 (15)	0.5456 (3)	0.28983 (8)	0.0470 (6)
N3	0.23670 (16)	0.5643 (3)	0.30811 (8)	0.0510 (6)
N4	0.10747 (17)	0.6026 (3)	0.34314 (8)	0.0495 (6)
N5	0.56724 (15)	0.9715 (3)	0.02807 (7)	0.0443 (6)
N6	0.69250 (16)	1.0300 (3)	−0.00807 (8)	0.0499 (6)
N7	0.49602 (17)	1.0170 (4)	−0.02594 (9)	0.0572 (7)
N8	0.62266 (19)	1.0377 (3)	−0.06399 (8)	0.0577 (7)
O1	0.28059 (16)	0.6373 (3)	0.24782 (8)	0.0690 (7)
O2	−0.00865 (18)	0.7355 (3)	0.32505 (8)	0.0686 (7)
O3	0.1077 (2)	0.2202 (3)	0.26096 (9)	0.0817 (9)
O4	0.03764 (19)	0.2645 (3)	0.31530 (9)	0.0741 (8)
O5	0.1689 (2)	0.3775 (4)	0.38514 (8)	0.0839 (9)
O6	0.23011 (17)	0.2846 (3)	0.33291 (8)	0.0654 (7)
O7	0.2129 (2)	0.7779 (3)	0.34178 (9)	0.0754 (8)
O8	0.44996 (17)	1.1140 (3)	0.03130 (8)	0.0730 (8)
O9	0.73452 (19)	1.1886 (3)	−0.05392 (9)	0.0775 (8)
O10	0.6443 (2)	0.7108 (3)	0.03228 (10)	0.0906 (10)
O11	0.7142 (3)	0.7511 (3)	−0.02225 (12)	0.1170 (16)
O12	0.5620 (3)	0.7904 (5)	−0.09416 (11)	0.1125 (13)
O13	0.5086 (3)	0.7245 (4)	−0.03819 (13)	0.1167 (15)
O14	0.5125 (2)	1.2048 (4)	−0.06979 (10)	0.0864 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.071 (2)	0.069 (2)	0.0479 (19)	−0.0004 (18)	−0.0081 (18)	0.0097 (17)
C2	0.074 (3)	0.089 (3)	0.067 (3)	0.019 (2)	−0.012 (2)	0.002 (2)
C3	0.066 (2)	0.104 (4)	0.078 (3)	0.001 (2)	0.011 (2)	−0.006 (3)
C4	0.086 (3)	0.097 (3)	0.067 (3)	−0.033 (3)	0.024 (2)	0.002 (2)
C5	0.089 (3)	0.059 (2)	0.055 (2)	−0.0141 (19)	0.0139 (19)	−0.0012 (17)
C6	0.0572 (18)	0.0624 (19)	0.0358 (15)	−0.0097 (15)	−0.0017 (14)	−0.0015 (14)
C7	0.064 (2)	0.065 (2)	0.0372 (17)	−0.0098 (17)	0.0019 (15)	−0.0018 (15)
C8	0.065 (2)	0.063 (2)	0.0363 (16)	−0.0109 (16)	−0.0017 (15)	−0.0025 (15)
C9	0.0528 (17)	0.0563 (19)	0.0426 (17)	−0.0070 (14)	−0.0041 (14)	−0.0018 (14)
C10	0.080 (2)	0.060 (2)	0.065 (2)	−0.0053 (19)	−0.005 (2)	0.0108 (18)
C11	0.078 (3)	0.062 (2)	0.088 (3)	0.015 (2)	−0.013 (2)	0.008 (2)
C12	0.0506 (18)	0.069 (2)	0.068 (2)	0.0120 (17)	−0.0027 (17)	−0.0013 (19)
C13	0.0417 (15)	0.0504 (16)	0.0390 (15)	−0.0022 (12)	−0.0026 (12)	−0.0028 (13)
C14	0.0442 (17)	0.0598 (19)	0.0474 (18)	0.0027 (14)	−0.0056 (14)	−0.0059 (15)
C15	0.0474 (16)	0.0572 (18)	0.0399 (17)	0.0074 (14)	0.0056 (13)	−0.0034 (14)
C16	0.0350 (14)	0.071 (2)	0.0544 (19)	0.0003 (14)	0.0014 (14)	−0.0021 (16)
C17	0.0362 (15)	0.0584 (18)	0.0498 (18)	−0.0017 (13)	0.0065 (13)	0.0055 (15)
C18	0.0482 (16)	0.0566 (18)	0.0409 (16)	−0.0020 (15)	0.0094 (13)	0.0028 (14)
C19	0.0390 (14)	0.0494 (16)	0.0403 (15)	−0.0038 (12)	0.0055 (12)	−0.0001 (13)
C20	0.0510 (17)	0.0566 (19)	0.0549 (19)	−0.0054 (15)	0.0046 (16)	−0.0007 (17)
C21	0.111 (4)	0.079 (3)	0.096 (4)	−0.036 (3)	0.020 (3)	0.003 (3)
C22	0.086 (3)	0.084 (4)	0.255 (10)	−0.019 (3)	−0.024 (5)	0.003 (5)
C23	0.0447 (15)	0.0511 (17)	0.0411 (16)	−0.0078 (13)	0.0027 (13)	0.0038 (13)
C24	0.0473 (16)	0.065 (2)	0.0458 (19)	−0.0060 (15)	−0.0003 (14)	0.0069 (15)
C25	0.070 (2)	0.080 (3)	0.077 (3)	0.010 (2)	−0.012 (2)	0.021 (2)
C26	0.085 (3)	0.060 (2)	0.114 (4)	0.014 (2)	−0.004 (3)	0.009 (2)
C27	0.065 (2)	0.089 (3)	0.062 (2)	−0.035 (2)	−0.0020 (19)	−0.002 (2)
C28	0.076 (2)	0.067 (2)	0.050 (2)	−0.0208 (19)	0.0067 (18)	−0.0119 (17)
C29	0.080 (3)	0.074 (3)	0.054 (2)	0.008 (2)	−0.011 (2)	−0.0128 (19)
C30	0.079 (3)	0.090 (3)	0.075 (3)	−0.010 (2)	−0.009 (2)	−0.003 (2)
C31	0.067 (3)	0.102 (4)	0.076 (3)	0.002 (2)	0.006 (2)	0.003 (3)
C32	0.094 (3)	0.083 (3)	0.068 (3)	0.030 (3)	0.023 (2)	0.000 (2)
C33	0.100 (3)	0.056 (2)	0.061 (2)	0.013 (2)	0.012 (2)	0.0011 (18)
C34	0.073 (2)	0.065 (2)	0.0382 (17)	0.0167 (18)	−0.0028 (16)	0.0017 (15)
C35	0.077 (2)	0.069 (2)	0.0405 (19)	0.0165 (18)	−0.0003 (18)	−0.0016 (17)
C36	0.074 (2)	0.059 (2)	0.0440 (18)	0.0159 (18)	−0.0028 (18)	−0.0042 (16)
C37	0.0622 (19)	0.0521 (18)	0.0522 (19)	0.0089 (15)	−0.0052 (16)	−0.0007 (15)
C38	0.091 (3)	0.058 (2)	0.082 (3)	0.000 (2)	−0.008 (3)	−0.012 (2)
C39	0.097 (3)	0.061 (3)	0.107 (4)	−0.016 (2)	−0.011 (3)	−0.011 (3)
C40	0.062 (2)	0.069 (2)	0.083 (3)	−0.0163 (19)	−0.005 (2)	0.012 (2)
C41	0.0455 (17)	0.0599 (19)	0.0512 (18)	−0.0029 (14)	−0.0059 (14)	0.0073 (15)
C42	0.0483 (17)	0.0500 (17)	0.0441 (17)	0.0032 (13)	−0.0079 (14)	0.0041 (14)
C43	0.0488 (17)	0.0543 (17)	0.0397 (17)	−0.0032 (14)	0.0043 (13)	0.0035 (14)
C44	0.0376 (15)	0.076 (2)	0.057 (2)	−0.0020 (15)	0.0057 (15)	0.0094 (18)
C45	0.0448 (16)	0.063 (2)	0.0452 (18)	0.0013 (15)	0.0055 (14)	−0.0009 (15)
C46	0.0562 (19)	0.062 (2)	0.053 (2)	0.0017 (16)	0.0133 (16)	0.0081 (16)
C47	0.0465 (15)	0.0509 (16)	0.0416 (17)	0.0011 (13)	0.0095 (13)	0.0018 (14)
C48	0.074 (2)	0.056 (2)	0.059 (2)	0.0104 (17)	0.0206 (18)	0.0075 (17)
C49	0.147 (6)	0.120 (5)	0.143 (6)	−0.004 (5)	0.063 (5)	−0.014 (5)
C50	0.133 (6)	0.145 (6)	0.148 (7)	0.006 (5)	0.012 (6)	0.010 (6)
C51	0.0516 (17)	0.065 (2)	0.0414 (17)	0.0012 (15)	0.0076 (14)	−0.0029 (15)
C52	0.074 (2)	0.094 (3)	0.065 (3)	−0.008 (2)	0.010 (2)	−0.029 (2)
C53	0.094 (6)	0.063 (5)	0.077 (7)	−0.006 (5)	−0.001 (5)	−0.001 (4)
C54	0.087 (7)	0.096 (10)	0.141 (14)	−0.012 (7)	0.006 (8)	0.014 (8)
C53'	0.091 (10)	0.083 (8)	0.070 (8)	−0.006 (7)	−0.003 (7)	−0.005 (6)
C54'	0.14 (2)	0.086 (13)	0.15 (2)	−0.052 (13)	0.038 (16)	−0.023 (12)
C55	0.067 (2)	0.103 (3)	0.061 (2)	0.018 (2)	−0.0098 (19)	0.006 (2)
C56	0.088 (3)	0.104 (3)	0.047 (2)	0.011 (3)	0.000 (2)	0.017 (2)
N1	0.0364 (12)	0.0522 (14)	0.0412 (14)	0.0019 (10)	0.0054 (10)	0.0012 (11)
N2	0.0382 (12)	0.0580 (15)	0.0448 (14)	0.0001 (11)	0.0055 (11)	−0.0049 (12)
N3	0.0419 (13)	0.0648 (17)	0.0464 (15)	−0.0133 (12)	0.0022 (11)	0.0038 (13)
N4	0.0529 (14)	0.0525 (15)	0.0431 (14)	−0.0035 (12)	0.0045 (12)	−0.0022 (12)
N5	0.0400 (12)	0.0550 (15)	0.0378 (13)	0.0014 (11)	0.0065 (11)	0.0009 (11)
N6	0.0416 (13)	0.0638 (16)	0.0444 (14)	0.0002 (12)	0.0086 (12)	0.0098 (13)
N7	0.0503 (15)	0.0757 (19)	0.0458 (16)	0.0084 (14)	−0.0030 (12)	−0.0033 (14)
N8	0.0626 (16)	0.0720 (18)	0.0384 (14)	0.0000 (14)	0.0035 (13)	0.0082 (13)
O1	0.0527 (13)	0.095 (2)	0.0588 (15)	−0.0194 (13)	0.0125 (12)	0.0155 (14)
O2	0.0739 (16)	0.0705 (16)	0.0615 (16)	0.0231 (14)	0.0091 (13)	−0.0069 (13)
O3	0.107 (2)	0.0566 (15)	0.082 (2)	−0.0094 (15)	0.0295 (18)	−0.0132 (14)
O4	0.0861 (18)	0.0634 (15)	0.0727 (18)	−0.0260 (14)	0.0203 (15)	0.0005 (13)
O5	0.116 (2)	0.091 (2)	0.0439 (15)	0.0180 (18)	0.0072 (15)	0.0133 (14)
O6	0.0671 (15)	0.0653 (15)	0.0637 (16)	0.0113 (13)	0.0036 (12)	0.0160 (13)
O7	0.0888 (19)	0.0672 (16)	0.0703 (17)	−0.0308 (15)	0.0092 (15)	−0.0110 (14)
O8	0.0594 (15)	0.101 (2)	0.0584 (16)	0.0269 (15)	0.0072 (13)	−0.0118 (15)
O9	0.0760 (17)	0.0829 (18)	0.0738 (18)	−0.0171 (15)	0.0159 (14)	0.0259 (15)
O10	0.127 (3)	0.0594 (16)	0.085 (2)	0.0206 (16)	0.042 (2)	0.0229 (15)
O11	0.164 (4)	0.076 (2)	0.111 (3)	0.061 (2)	0.079 (3)	0.032 (2)
O12	0.131 (3)	0.136 (3)	0.070 (2)	−0.027 (3)	0.024 (2)	−0.046 (2)
O13	0.139 (3)	0.099 (3)	0.112 (3)	−0.061 (2)	0.056 (3)	−0.046 (2)
O14	0.091 (2)	0.098 (2)	0.0707 (19)	0.0185 (18)	−0.0123 (17)	0.0211 (17)

Geometric parameters (Å, º) top

C1—C2	1.380 (6)	C30—H30	0.9300
C1—C6	1.389 (5)	C31—C32	1.354 (7)
C1—H1	0.9300	C31—H31	0.9300
C2—C3	1.346 (7)	C32—C33	1.398 (7)
C2—H2	0.9300	C32—H32	0.9300
C3—C4	1.382 (7)	C33—C34	1.392 (5)
C3—H3	0.9300	C33—H33	0.9300
C4—C5	1.378 (6)	C34—C35	1.442 (6)
C4—H4	0.9300	C35—C36	1.195 (6)
C5—C6	1.392 (5)	C36—C37	1.427 (6)
C5—H5	0.9300	C37—C38	1.397 (6)
C6—C7	1.443 (5)	C37—C42	1.413 (5)
C7—C8	1.185 (5)	C38—C39	1.353 (7)
C8—C9	1.441 (5)	C38—H38	0.9300
C9—C10	1.394 (5)	C39—C40	1.386 (7)
C9—C13	1.401 (5)	C39—H39	0.9300
C10—C11	1.370 (6)	C40—C41	1.396 (5)
C10—H10	0.9300	C40—H40	0.9300
C11—C12	1.376 (6)	C41—C42	1.406 (5)
C11—H11	0.9300	C41—C44	1.503 (5)
C12—C14	1.385 (5)	C42—C43	1.509 (5)
C12—H12	0.9300	C43—N5	1.452 (4)
C13—C14	1.396 (5)	C43—H43A	0.9700
C13—C15	1.517 (4)	C43—H43B	0.9700
C14—C16	1.515 (5)	C44—N6	1.460 (5)
C15—N1	1.458 (4)	C44—H44A	0.9700
C15—H15A	0.9700	C44—H44B	0.9700
C15—H15B	0.9700	C45—O8	1.201 (4)
C16—N2	1.458 (4)	C45—N5	1.380 (4)
C16—H16A	0.9700	C45—N7	1.384 (5)
C16—H16B	0.9700	C46—O9	1.204 (4)
C17—O1	1.210 (4)	C46—N6	1.346 (5)
C17—N1	1.364 (4)	C46—N8	1.407 (5)
C17—N3	1.391 (5)	C47—N5	1.443 (4)
C18—O2	1.207 (4)	C47—N6	1.447 (4)
C18—N2	1.362 (4)	C47—C48	1.538 (5)
C18—N4	1.395 (4)	C47—C51	1.552 (5)
C19—N1	1.445 (4)	C48—O10	1.184 (5)
C19—N2	1.448 (4)	C48—O11	1.310 (5)
C19—C20	1.537 (5)	C49—C50	1.360 (10)
C19—C23	1.567 (5)	C49—O11	1.573 (9)
C20—O3	1.193 (4)	C49—H49A	0.9700
C20—O4	1.314 (4)	C49—H49B	0.9700
C21—C22	1.468 (9)	C50—H50A	0.9600
C21—O4	1.486 (5)	C50—H50B	0.9600
C21—H21A	0.9700	C50—H50C	0.9600
C21—H21B	0.9700	C51—N8	1.447 (5)
C22—H22A	0.9600	C51—N7	1.453 (4)
C22—H22B	0.9600	C51—C52	1.545 (6)
C22—H22C	0.9600	C52—O12	1.187 (6)
C23—N4	1.450 (4)	C52—O13	1.296 (6)
C23—N3	1.453 (4)	C53—C54	1.486 (8)
C23—C24	1.534 (5)	C53—O13	1.513 (10)
C24—O5	1.194 (4)	C53—H53A	0.9700
C24—O6	1.315 (4)	C53—H53B	0.9700
C25—O6	1.467 (5)	C54—H54A	0.9600
C25—C26	1.473 (7)	C54—H54B	0.9600
C25—H25A	0.9700	C54—H54C	0.9600
C25—H25B	0.9700	C53'—C54'	1.496 (9)
C26—H26A	0.9600	C53'—O13	1.566 (14)
C26—H26B	0.9600	C53'—H53C	0.9700
C26—H26C	0.9600	C53'—H53D	0.9700
C27—O7	1.415 (6)	C54'—H54D	0.9600
C27—N3	1.458 (5)	C54'—H54E	0.9600
C27—H27A	0.9700	C54'—H54F	0.9600
C27—H27B	0.9700	C55—O14	1.412 (6)
C28—O7	1.411 (5)	C55—N7	1.456 (5)
C28—N4	1.452 (4)	C55—H55A	0.9700
C28—H28A	0.9700	C55—H55B	0.9700
C28—H28B	0.9700	C56—O14	1.426 (6)
C29—C30	1.371 (6)	C56—N8	1.451 (5)
C29—C34	1.385 (6)	C56—H56A	0.9700
C29—H29	0.9300	C56—H56B	0.9700
C30—C31	1.351 (7)

C2—C1—C6	120.7 (4)	C35—C36—C37	177.1 (4)
C2—C1—H1	119.7	C38—C37—C42	119.8 (4)
C6—C1—H1	119.7	C38—C37—C36	119.0 (4)
C3—C2—C1	120.4 (4)	C42—C37—C36	121.2 (3)
C3—C2—H2	119.8	C39—C38—C37	120.6 (4)
C1—C2—H2	119.8	C39—C38—H38	119.7
C2—C3—C4	120.2 (4)	C37—C38—H38	119.7
C2—C3—H3	119.9	C38—C39—C40	120.7 (4)
C4—C3—H3	119.9	C38—C39—H39	119.7
C5—C4—C3	120.5 (4)	C40—C39—H39	119.7
C5—C4—H4	119.8	C39—C40—C41	120.6 (4)
C3—C4—H4	119.8	C39—C40—H40	119.7
C4—C5—C6	119.7 (4)	C41—C40—H40	119.7
C4—C5—H5	120.1	C40—C41—C42	119.2 (4)
C6—C5—H5	120.1	C40—C41—C44	118.5 (3)
C1—C6—C5	118.5 (4)	C42—C41—C44	122.1 (3)
C1—C6—C7	120.8 (3)	C41—C42—C37	119.1 (3)
C5—C6—C7	120.7 (4)	C41—C42—C43	121.4 (3)
C8—C7—C6	179.5 (4)	C37—C42—C43	119.4 (3)
C7—C8—C9	177.7 (4)	N5—C43—C42	115.4 (3)
C10—C9—C13	119.8 (3)	N5—C43—H43A	108.4
C10—C9—C8	118.3 (3)	C42—C43—H43A	108.4
C13—C9—C8	121.9 (3)	N5—C43—H43B	108.4
C11—C10—C9	120.3 (4)	C42—C43—H43B	108.4
C11—C10—H10	119.9	H43A—C43—H43B	107.5
C9—C10—H10	119.9	N6—C44—C41	115.7 (3)
C10—C11—C12	120.2 (4)	N6—C44—H44A	108.3
C10—C11—H11	119.9	C41—C44—H44A	108.3
C12—C11—H11	119.9	N6—C44—H44B	108.3
C11—C12—C14	120.8 (4)	C41—C44—H44B	108.3
C11—C12—H12	119.6	H44A—C44—H44B	107.4
C14—C12—H12	119.6	O8—C45—N5	126.0 (3)
C14—C13—C9	119.1 (3)	O8—C45—N7	126.3 (3)
C14—C13—C15	121.1 (3)	N5—C45—N7	107.6 (3)
C9—C13—C15	119.7 (3)	O9—C46—N6	127.6 (4)
C12—C14—C13	119.7 (3)	O9—C46—N8	123.8 (3)
C12—C14—C16	118.9 (3)	N6—C46—N8	108.6 (3)
C13—C14—C16	121.3 (3)	N5—C47—N6	113.2 (3)
N1—C15—C13	113.6 (3)	N5—C47—C48	111.2 (3)
N1—C15—H15A	108.8	N6—C47—C48	110.3 (3)
C13—C15—H15A	108.8	N5—C47—C51	103.9 (2)
N1—C15—H15B	108.8	N6—C47—C51	102.2 (3)
C13—C15—H15B	108.8	C48—C47—C51	115.8 (3)
H15A—C15—H15B	107.7	O10—C48—O11	126.3 (4)
N2—C16—C14	114.8 (3)	O10—C48—C47	124.8 (3)
N2—C16—H16A	108.6	O11—C48—C47	108.8 (3)
C14—C16—H16A	108.6	C50—C49—O11	96.7 (7)
N2—C16—H16B	108.6	C50—C49—H49A	112.4
C14—C16—H16B	108.6	O11—C49—H49A	112.4
H16A—C16—H16B	107.5	C50—C49—H49B	112.4
O1—C17—N1	126.5 (3)	O11—C49—H49B	112.4
O1—C17—N3	125.3 (3)	H49A—C49—H49B	110.0
N1—C17—N3	108.1 (3)	C49—C50—H50A	109.5
O2—C18—N2	126.3 (3)	C49—C50—H50B	109.5
O2—C18—N4	125.7 (3)	H50A—C50—H50B	109.5
N2—C18—N4	107.9 (3)	C49—C50—H50C	109.5
N1—C19—N2	113.7 (3)	H50A—C50—H50C	109.5
N1—C19—C20	110.5 (3)	H50B—C50—H50C	109.5
N2—C19—C20	111.7 (2)	N8—C51—N7	112.4 (3)
N1—C19—C23	103.5 (2)	N8—C51—C52	110.7 (3)
N2—C19—C23	102.1 (2)	N7—C51—C52	109.2 (3)
C20—C19—C23	114.9 (3)	N8—C51—C47	104.8 (3)
O3—C20—O4	125.4 (3)	N7—C51—C47	102.8 (2)
O3—C20—C19	123.7 (3)	C52—C51—C47	116.8 (3)
O4—C20—C19	110.9 (3)	O12—C52—O13	125.6 (4)
C22—C21—O4	109.5 (5)	O12—C52—C51	123.7 (5)
C22—C21—H21A	109.8	O13—C52—C51	110.7 (3)
O4—C21—H21A	109.8	C54—C53—O13	100.6 (10)
C22—C21—H21B	109.8	C54—C53—H53A	111.7
O4—C21—H21B	109.8	O13—C53—H53A	111.7
H21A—C21—H21B	108.2	C54—C53—H53B	111.7
C21—C22—H22A	109.5	O13—C53—H53B	111.7
C21—C22—H22B	109.5	H53A—C53—H53B	109.4
H22A—C22—H22B	109.5	C54'—C53'—O13	100.0 (13)
C21—C22—H22C	109.5	C54'—C53'—H53C	111.8
H22A—C22—H22C	109.5	O13—C53'—H53C	111.8
H22B—C22—H22C	109.5	C54'—C53'—H53D	111.8
N4—C23—N3	112.2 (3)	O13—C53'—H53D	111.8
N4—C23—C24	111.6 (3)	H53C—C53'—H53D	109.5
N3—C23—C24	109.6 (3)	C53'—C54'—H54D	109.5
N4—C23—C19	104.3 (2)	C53'—C54'—H54E	109.5
N3—C23—C19	102.9 (2)	H54D—C54'—H54E	109.5
C24—C23—C19	116.0 (3)	C53'—C54'—H54F	109.5
O5—C24—O6	126.0 (3)	H54D—C54'—H54F	109.5
O5—C24—C23	124.1 (3)	H54E—C54'—H54F	109.5
O6—C24—C23	109.9 (3)	O14—C55—N7	110.5 (3)
O6—C25—C26	107.6 (4)	O14—C55—H55A	109.5
O6—C25—H25A	110.2	N7—C55—H55A	109.5
C26—C25—H25A	110.2	O14—C55—H55B	109.5
O6—C25—H25B	110.2	N7—C55—H55B	109.5
C26—C25—H25B	110.2	H55A—C55—H55B	108.1
H25A—C25—H25B	108.5	O14—C56—N8	110.7 (3)
C25—C26—H26A	109.5	O14—C56—H56A	109.5
C25—C26—H26B	109.5	N8—C56—H56A	109.5
H26A—C26—H26B	109.5	O14—C56—H56B	109.5
C25—C26—H26C	109.5	N8—C56—H56B	109.5
H26A—C26—H26C	109.5	H56A—C56—H56B	108.1
H26B—C26—H26C	109.5	C17—N1—C19	111.8 (2)
O7—C27—N3	111.0 (3)	C17—N1—C15	120.9 (3)
O7—C27—H27A	109.4	C19—N1—C15	122.5 (2)
N3—C27—H27A	109.4	C18—N2—C19	113.5 (3)
O7—C27—H27B	109.4	C18—N2—C16	121.8 (3)
N3—C27—H27B	109.4	C19—N2—C16	121.6 (3)
H27A—C27—H27B	108.0	C17—N3—C23	111.4 (3)
O7—C28—N4	110.9 (3)	C17—N3—C27	121.5 (3)
O7—C28—H28A	109.5	C23—N3—C27	115.6 (3)
N4—C28—H28A	109.5	C18—N4—C23	110.7 (3)
O7—C28—H28B	109.5	C18—N4—C28	118.0 (3)
N4—C28—H28B	109.5	C23—N4—C28	116.5 (3)
H28A—C28—H28B	108.1	C45—N5—C47	110.8 (3)
C30—C29—C34	120.0 (4)	C45—N5—C43	121.3 (3)
C30—C29—H29	120.0	C47—N5—C43	122.3 (2)
C34—C29—H29	120.0	C46—N6—C47	113.6 (3)
C31—C30—C29	121.3 (5)	C46—N6—C44	124.3 (3)
C31—C30—H30	119.4	C47—N6—C44	121.4 (3)
C29—C30—H30	119.4	C45—N7—C51	111.9 (3)
C30—C31—C32	119.9 (5)	C45—N7—C55	122.1 (3)
C30—C31—H31	120.1	C51—N7—C55	116.7 (3)
C32—C31—H31	120.1	C46—N8—C51	109.5 (3)
C31—C32—C33	120.9 (4)	C46—N8—C56	118.9 (3)
C31—C32—H32	119.5	C51—N8—C56	115.4 (3)
C33—C32—H32	119.5	C20—O4—C21	115.8 (3)
C34—C33—C32	118.8 (4)	C24—O6—C25	118.3 (3)
C34—C33—H33	120.6	C28—O7—C27	110.2 (3)
C32—C33—H33	120.6	C48—O11—C49	116.1 (4)
C29—C34—C33	119.0 (4)	C52—O13—C53	123.4 (6)
C29—C34—C35	120.6 (3)	C52—O13—C53'	102.7 (6)
C33—C34—C35	120.4 (4)	C53—O13—C53'	33.4 (5)
C36—C35—C34	178.4 (4)	C55—O14—C56	110.1 (4)

C6—C1—C2—C3	1.2 (6)	N2—C19—N1—C15	−58.2 (4)
C1—C2—C3—C4	−1.4 (7)	C20—C19—N1—C15	68.4 (4)
C2—C3—C4—C5	0.7 (8)	C23—C19—N1—C15	−168.1 (3)
C3—C4—C5—C6	0.1 (7)	C13—C15—N1—C17	−75.7 (3)
C2—C1—C6—C5	−0.4 (6)	C13—C15—N1—C19	77.7 (4)
C2—C1—C6—C7	179.7 (4)	O2—C18—N2—C19	171.9 (3)
C4—C5—C6—C1	−0.3 (6)	N4—C18—N2—C19	−11.1 (3)
C4—C5—C6—C7	179.7 (4)	O2—C18—N2—C16	11.5 (5)
C1—C6—C7—C8	−33 (49)	N4—C18—N2—C16	−171.5 (3)
C5—C6—C7—C8	147 (100)	N1—C19—N2—C18	−106.1 (3)
C6—C7—C8—C9	−159 (100)	C20—C19—N2—C18	128.0 (3)
C7—C8—C9—C10	32 (9)	C23—C19—N2—C18	4.7 (3)
C7—C8—C9—C13	−149 (9)	N1—C19—N2—C16	54.4 (4)
C13—C9—C10—C11	1.4 (6)	C20—C19—N2—C16	−71.5 (4)
C8—C9—C10—C11	−179.7 (4)	C23—C19—N2—C16	165.2 (3)
C9—C10—C11—C12	−1.3 (6)	C14—C16—N2—C18	84.7 (4)
C10—C11—C12—C14	−0.9 (6)	C14—C16—N2—C19	−74.1 (4)
C10—C9—C13—C14	0.5 (5)	O1—C17—N3—C23	169.8 (3)
C8—C9—C13—C14	−178.4 (3)	N1—C17—N3—C23	−13.1 (4)
C10—C9—C13—C15	178.7 (3)	O1—C17—N3—C27	28.0 (6)
C8—C9—C13—C15	−0.1 (5)	N1—C17—N3—C27	−154.9 (3)
C11—C12—C14—C13	2.8 (6)	N4—C23—N3—C17	−106.4 (3)
C11—C12—C14—C16	−174.1 (4)	C24—C23—N3—C17	129.0 (3)
C9—C13—C14—C12	−2.5 (5)	C19—C23—N3—C17	5.0 (4)
C15—C13—C14—C12	179.2 (3)	N4—C23—N3—C27	37.7 (4)
C9—C13—C14—C16	174.2 (3)	C24—C23—N3—C27	−86.8 (4)
C15—C13—C14—C16	−4.0 (5)	C19—C23—N3—C27	149.2 (3)
C14—C13—C15—N1	−56.4 (4)	O7—C27—N3—C17	90.2 (4)
C9—C13—C15—N1	125.4 (3)	O7—C27—N3—C23	−50.1 (4)
C12—C14—C16—N2	−121.4 (3)	O2—C18—N4—C23	−169.9 (3)
C13—C14—C16—N2	61.8 (4)	N2—C18—N4—C23	13.1 (3)
N1—C19—C20—O3	−3.4 (5)	O2—C18—N4—C28	−32.1 (5)
N2—C19—C20—O3	124.3 (4)	N2—C18—N4—C28	150.9 (3)
C23—C19—C20—O3	−120.0 (4)	N3—C23—N4—C18	100.7 (3)
N1—C19—C20—O4	177.3 (3)	C24—C23—N4—C18	−135.8 (3)
N2—C19—C20—O4	−55.0 (4)	C19—C23—N4—C18	−9.9 (3)
C23—C19—C20—O4	60.7 (4)	N3—C23—N4—C28	−37.8 (4)
N1—C19—C23—N4	121.5 (2)	C24—C23—N4—C28	85.7 (3)
N2—C19—C23—N4	3.2 (3)	C19—C23—N4—C28	−148.4 (3)
C20—C19—C23—N4	−117.9 (3)	O7—C28—N4—C18	−85.5 (4)
N1—C19—C23—N3	4.2 (3)	O7—C28—N4—C23	49.8 (4)
N2—C19—C23—N3	−114.1 (3)	O8—C45—N5—C47	−165.7 (4)
C20—C19—C23—N3	124.8 (3)	N7—C45—N5—C47	18.1 (4)
N1—C19—C23—C24	−115.4 (3)	O8—C45—N5—C43	−11.4 (5)
N2—C19—C23—C24	126.3 (3)	N7—C45—N5—C43	172.4 (3)
C20—C19—C23—C24	5.1 (4)	N6—C47—N5—C45	93.6 (3)
N4—C23—C24—O5	−5.2 (5)	C48—C47—N5—C45	−141.6 (3)
N3—C23—C24—O5	119.7 (4)	C51—C47—N5—C45	−16.4 (3)
C19—C23—C24—O5	−124.4 (4)	N6—C47—N5—C43	−60.4 (4)
N4—C23—C24—O6	175.6 (3)	C48—C47—N5—C43	64.3 (4)
N3—C23—C24—O6	−59.5 (4)	C51—C47—N5—C43	−170.4 (3)
C19—C23—C24—O6	56.4 (3)	C42—C43—N5—C45	−75.3 (4)
C34—C29—C30—C31	0.9 (7)	C42—C43—N5—C47	76.0 (4)
C29—C30—C31—C32	−0.7 (8)	O9—C46—N6—C47	176.6 (4)
C30—C31—C32—C33	−0.9 (8)	N8—C46—N6—C47	−5.7 (4)
C31—C32—C33—C34	2.4 (7)	O9—C46—N6—C44	6.6 (6)
C30—C29—C34—C33	0.6 (6)	N8—C46—N6—C44	−175.7 (3)
C30—C29—C34—C35	179.2 (4)	N5—C47—N6—C46	−112.8 (3)
C32—C33—C34—C29	−2.2 (6)	C48—C47—N6—C46	122.0 (3)
C32—C33—C34—C35	179.2 (4)	C51—C47—N6—C46	−1.7 (3)
C29—C34—C35—C36	41 (16)	N5—C47—N6—C44	57.5 (4)
C33—C34—C35—C36	−141 (15)	C48—C47—N6—C44	−67.7 (4)
C34—C35—C36—C37	109 (16)	C51—C47—N6—C44	168.6 (3)
C35—C36—C37—C38	45 (8)	C41—C44—N6—C46	95.5 (4)
C35—C36—C37—C42	−134 (8)	C41—C44—N6—C47	−73.7 (4)
C42—C37—C38—C39	1.3 (7)	O8—C45—N7—C51	171.8 (4)
C36—C37—C38—C39	−178.1 (4)	N5—C45—N7—C51	−12.1 (4)
C37—C38—C39—C40	−1.7 (8)	O8—C45—N7—C55	26.3 (6)
C38—C39—C40—C41	−0.2 (7)	N5—C45—N7—C55	−157.6 (3)
C39—C40—C41—C42	2.4 (6)	N8—C51—N7—C45	−110.2 (3)
C39—C40—C41—C44	−172.4 (4)	C52—C51—N7—C45	126.5 (4)
C40—C41—C42—C37	−2.7 (5)	C47—C51—N7—C45	1.9 (4)
C44—C41—C42—C37	171.9 (3)	N8—C51—N7—C55	37.3 (4)
C40—C41—C42—C43	−178.8 (3)	C52—C51—N7—C55	−86.0 (4)
C44—C41—C42—C43	−4.2 (5)	C47—C51—N7—C55	149.4 (3)
C38—C37—C42—C41	0.9 (5)	O14—C55—N7—C45	95.3 (4)
C36—C37—C42—C41	−179.7 (3)	O14—C55—N7—C51	−48.7 (5)
C38—C37—C42—C43	177.1 (3)	O9—C46—N8—C51	−170.9 (4)
C36—C37—C42—C43	−3.5 (5)	N6—C46—N8—C51	11.3 (4)
C41—C42—C43—N5	−53.4 (4)	O9—C46—N8—C56	−35.2 (5)
C37—C42—C43—N5	130.6 (3)	N6—C46—N8—C56	147.0 (3)
C40—C41—C44—N6	−126.4 (4)	N7—C51—N8—C46	98.9 (3)
C42—C41—C44—N6	59.0 (4)	C52—C51—N8—C46	−138.7 (3)
N5—C47—C48—O10	−0.6 (6)	C47—C51—N8—C46	−12.0 (4)
N6—C47—C48—O10	125.7 (5)	N7—C51—N8—C56	−38.5 (4)
C51—C47—C48—O10	−118.9 (5)	C52—C51—N8—C56	83.9 (4)
N5—C47—C48—O11	−178.1 (4)	C47—C51—N8—C56	−149.4 (3)
N6—C47—C48—O11	−51.7 (4)	O14—C56—N8—C46	−81.7 (5)
C51—C47—C48—O11	63.6 (4)	O14—C56—N8—C51	51.5 (5)
N5—C47—C51—N8	126.1 (3)	O3—C20—O4—C21	6.0 (6)
N6—C47—C51—N8	8.1 (3)	C19—C20—O4—C21	−174.7 (4)
C48—C47—C51—N8	−111.7 (3)	C22—C21—O4—C20	−83.0 (6)
N5—C47—C51—N7	8.4 (3)	O5—C24—O6—C25	1.8 (6)
N6—C47—C51—N7	−109.5 (3)	C23—C24—O6—C25	−179.1 (3)
C48—C47—C51—N7	130.6 (3)	C26—C25—O6—C24	−173.8 (3)
N5—C47—C51—C52	−111.1 (3)	N4—C28—O7—C27	−60.6 (4)
N6—C47—C51—C52	131.0 (3)	N3—C27—O7—C28	61.0 (4)
C48—C47—C51—C52	11.1 (4)	O10—C48—O11—C49	−6.8 (8)
N8—C51—C52—O12	−6.6 (6)	C47—C48—O11—C49	170.6 (5)
N7—C51—C52—O12	117.7 (5)	C50—C49—O11—C48	88.4 (7)
C47—C51—C52—O12	−126.3 (5)	O12—C52—O13—C53	13.1 (10)
N8—C51—C52—O13	174.5 (4)	C51—C52—O13—C53	−168.0 (7)
N7—C51—C52—O13	−61.3 (5)	O12—C52—O13—C53'	−15.7 (10)
C47—C51—C52—O13	54.7 (5)	C51—C52—O13—C53'	163.3 (8)
O1—C17—N1—C19	−166.7 (3)	C54—C53—O13—C52	−102.9 (11)
N3—C17—N1—C19	16.3 (4)	C54—C53—O13—C53'	−44.4 (12)
O1—C17—N1—C15	−10.7 (5)	C54'—C53'—O13—C52	−174.1 (17)
N3—C17—N1—C15	172.2 (3)	C54'—C53'—O13—C53	52.7 (17)
N2—C19—N1—C17	97.3 (3)	N7—C55—O14—C56	60.1 (5)
C20—C19—N1—C17	−136.1 (3)	N8—C56—O14—C55	−62.1 (5)
C23—C19—N1—C17	−12.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C40—H40···O8ⁱ	0.93	2.50	3.383 (5)	159
C50—H50B···O9ⁱⁱ	0.96	2.39	3.269 (10)	151
C12—H12···O1ⁱⁱⁱ	0.93	2.44	3.337 (4)	163
C25—H25B···O12^iv	0.97	2.56	3.392 (6)	144

Symmetry codes: (i) x+1/2, −y+5/2, z; (ii) x, y−1, z; (iii) x−1/2, −y+3/2, z; (iv) −x+1, −y+1, z+1/2.

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