The title compound, C
28H
26N
4O
7, (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.
Supporting information
CCDC reference: 628400
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
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-1
H,3
H,4
H,11
H-2-oxa-
3a,4a,10
a,11
a-tetraazabenz[
f]indeno[2,1,7-ija]azulene-11
b,11
c-dicarboxylate
top
Crystal data top
C28H26N4O7 | F(000) = 2224 |
Mr = 530.53 | Dx = 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 | Rint = 0.037 |
Graphite monochromator | θmax = 28.3°, θmin = 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(Fo2) + (0.089P)2 + 0.1756P] where P = (Fo2 + 2Fc2)/3 |
6494 reflections | (Δ/σ)max < 0.001 |
727 parameters | Δρmax = 0.28 e Å−3 |
3 restraints | Δρmin = −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 | Uiso*/Ueq | 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···O12iv | 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. |