In the title compound, C
28H
24N
2O
3, the two molecules in the asymmetric unit have different conformations about the ether bonds. The bond lengths and angles of the two molecules are nearly identical. The crystal structure is stabilized by intramolecular O—H
N and intermolecular C—H
O hydrogen bonding.
Supporting information
CCDC reference: 608435
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.006 Å
- R factor = 0.068
- wR factor = 0.214
- Data-to-parameter ratio = 14.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 38 Perc.
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.118
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.20
PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C2 .. 6.36 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C17 - C18 .. 5.51 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C38 - C39 .. 5.86 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O5
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8B .. O3 .. 2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H49B .. O4 .. 2.61 Ang.
PLAT755_ALERT_4_C D-H Calc 0.96000, Rep 0.960(4) ...... Senseless su
C8 -H8B 1.555 1.555
PLAT755_ALERT_4_C D-H Calc 0.96000, Rep 0.960(4) ...... Senseless su
C49 -H49B 1.555 1.555
PLAT756_ALERT_4_C H...A Calc 2.63000, Rep 2.626(3) ...... Senseless su
H8B -O3 1.555 2.566
PLAT756_ALERT_4_C H...A Calc 2.61000, Rep 2.613(3) ...... Senseless su
H49B -O4 1.555 2.676
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
18 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
7 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Bis{4-[2-(2-hydroxyphenyl)ethyleneamino]phenyl} ether
top
Crystal data top
C28H24N2O3 | Z = 4 |
Mr = 436.49 | F(000) = 920 |
Triclinic, P1 | Dx = 1.301 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.4897 (8) Å | Cell parameters from 26681 reflections |
b = 10.4644 (8) Å | θ = 1.8–26.1° |
c = 22.8605 (19) Å | µ = 0.09 mm−1 |
α = 96.588 (6)° | T = 296 K |
β = 98.781 (7)° | Plate, colourless |
γ = 89.957 (6)° | 0.35 × 0.26 × 0.08 mm |
V = 2228.4 (3) Å3 | |
Data collection top
Stoe IPDS-2 diffractometer | 8425 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 3164 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.118 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 1.8° |
ω scans | h = −11→11 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −12→12 |
Tmin = 0.971, Tmax = 0.993 | l = −28→28 |
27310 measured reflections | |
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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.214 | H-atom parameters constrained |
S = 0.89 | w = 1/[σ2(Fo2) + (0.0985P)2] where P = (Fo2 + 2Fc2)/3 |
8425 reflections | (Δ/σ)max < 0.001 |
596 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Special details top
Experimental. MS (m/z): 436, 317, 210, 139, 91. |
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs 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 | |
O1 | 0.3093 (3) | 0.4576 (3) | 0.20696 (12) | 0.0651 (11) | |
O2 | 0.3476 (4) | 0.3151 (4) | 0.48312 (13) | 0.0875 (13) | |
O3 | 0.2092 (3) | 0.6042 (3) | 0.79583 (12) | 0.0617 (11) | |
N1 | 0.1818 (3) | 0.3470 (3) | 0.27807 (13) | 0.0494 (11) | |
N2 | 0.3212 (3) | 0.4484 (3) | 0.72389 (13) | 0.0496 (11) | |
C1 | 0.1462 (4) | 0.2770 (4) | 0.17523 (15) | 0.0445 (12) | |
C2 | 0.2425 (4) | 0.3722 (4) | 0.16305 (16) | 0.0452 (12) | |
C3 | 0.2686 (6) | 0.3767 (4) | 0.10537 (19) | 0.0665 (17) | |
C4 | 0.2049 (6) | 0.2941 (5) | 0.06011 (19) | 0.072 (2) | |
C5 | 0.1099 (5) | 0.2001 (5) | 0.06978 (18) | 0.0673 (18) | |
C6 | 0.0834 (5) | 0.1931 (4) | 0.12629 (18) | 0.0573 (17) | |
C7 | 0.1155 (4) | 0.2682 (4) | 0.23510 (16) | 0.0429 (12) | |
C8 | 0.0131 (4) | 0.1662 (4) | 0.24438 (18) | 0.0542 (16) | |
C9 | 0.1554 (5) | 0.3512 (4) | 0.33799 (17) | 0.0540 (16) | |
C10 | 0.0201 (5) | 0.3967 (5) | 0.35282 (19) | 0.0667 (17) | |
C11 | −0.0025 (5) | 0.4075 (5) | 0.4098 (2) | 0.0753 (19) | |
C12 | 0.1049 (5) | 0.3806 (5) | 0.4547 (2) | 0.0747 (19) | |
C13 | 0.2335 (5) | 0.3436 (4) | 0.44110 (18) | 0.0619 (16) | |
C14 | 0.2588 (4) | 0.3303 (4) | 0.38341 (17) | 0.0579 (14) | |
C15 | 0.3398 (6) | 0.3496 (6) | 0.54321 (19) | 0.079 (2) | |
C16 | 0.3923 (6) | 0.4602 (6) | 0.5704 (2) | 0.083 (2) | |
C17 | 0.3890 (6) | 0.4929 (5) | 0.6320 (2) | 0.0746 (19) | |
C18 | 0.3339 (4) | 0.4131 (5) | 0.66375 (16) | 0.0570 (14) | |
C19 | 0.2751 (6) | 0.2917 (5) | 0.6341 (2) | 0.0755 (19) | |
C20 | 0.2785 (6) | 0.2611 (5) | 0.5741 (2) | 0.0796 (19) | |
C21 | 0.4904 (4) | 0.2845 (4) | 0.75761 (18) | 0.0570 (14) | |
C22 | 0.3873 (4) | 0.3896 (4) | 0.76663 (15) | 0.0415 (11) | |
C23 | 0.3611 (4) | 0.4332 (4) | 0.82747 (16) | 0.0442 (12) | |
C24 | 0.2725 (4) | 0.5379 (4) | 0.83961 (17) | 0.0507 (14) | |
C25 | 0.2486 (5) | 0.5747 (5) | 0.89705 (18) | 0.0653 (16) | |
C26 | 0.3076 (6) | 0.5103 (5) | 0.94308 (19) | 0.075 (2) | |
C27 | 0.3944 (6) | 0.4081 (5) | 0.93213 (19) | 0.070 (2) | |
C28 | 0.4201 (4) | 0.3708 (4) | 0.87543 (16) | 0.0535 (16) | |
O4 | 0.2923 (3) | 0.9565 (3) | 0.20405 (12) | 0.0606 (10) | |
O5 | 0.1511 (4) | 0.8257 (4) | 0.51688 (13) | 0.0884 (13) | |
O6 | 0.1895 (3) | 1.1044 (3) | 0.79365 (12) | 0.0619 (11) | |
N3 | 0.1798 (3) | 0.8362 (3) | 0.27589 (13) | 0.0498 (11) | |
N4 | 0.3175 (3) | 0.9579 (3) | 0.72203 (13) | 0.0492 (11) | |
C29 | 0.1403 (4) | 0.7699 (4) | 0.17191 (16) | 0.0449 (12) | |
C30 | 0.2271 (4) | 0.8669 (4) | 0.16055 (16) | 0.0500 (16) | |
C31 | 0.2530 (5) | 0.8764 (5) | 0.10239 (19) | 0.0656 (17) | |
C32 | 0.1912 (6) | 0.7876 (5) | 0.0561 (2) | 0.071 (2) | |
C33 | 0.1046 (6) | 0.6922 (5) | 0.06670 (18) | 0.069 (2) | |
C34 | 0.0786 (5) | 0.6830 (4) | 0.12388 (17) | 0.0567 (16) | |
C35 | 0.1130 (4) | 0.7562 (4) | 0.23343 (15) | 0.0423 (12) | |
C36 | 0.0102 (4) | 0.6565 (4) | 0.24192 (18) | 0.0545 (14) | |
C37 | 0.1662 (4) | 0.8309 (4) | 0.33623 (16) | 0.0527 (14) | |
C38 | 0.1100 (6) | 0.9256 (5) | 0.36817 (19) | 0.0734 (19) | |
C39 | 0.1060 (6) | 0.9236 (6) | 0.4291 (2) | 0.088 (2) | |
C40 | 0.1609 (6) | 0.8265 (6) | 0.45611 (19) | 0.076 (2) | |
C41 | 0.2219 (6) | 0.7231 (5) | 0.4258 (2) | 0.078 (2) | |
C42 | 0.2257 (6) | 0.7233 (5) | 0.3659 (2) | 0.0744 (19) | |
C43 | 0.2667 (5) | 0.8719 (4) | 0.55938 (19) | 0.0617 (16) | |
C44 | 0.3966 (5) | 0.9014 (5) | 0.5446 (2) | 0.0740 (19) | |
C45 | 0.5016 (5) | 0.9519 (5) | 0.59056 (19) | 0.0675 (17) | |
C46 | 0.4783 (5) | 0.9719 (5) | 0.6474 (2) | 0.0686 (17) | |
C47 | 0.3441 (5) | 0.9303 (4) | 0.66214 (16) | 0.0535 (16) | |
C48 | 0.2412 (5) | 0.8893 (4) | 0.61717 (17) | 0.0583 (14) | |
C49 | 0.4869 (4) | 0.7944 (4) | 0.75599 (17) | 0.0523 (12) | |
C50 | 0.3831 (4) | 0.9012 (4) | 0.76516 (16) | 0.0434 (12) | |
C51 | 0.3528 (4) | 0.9406 (4) | 0.82580 (16) | 0.0458 (12) | |
C52 | 0.2570 (4) | 1.0396 (4) | 0.83704 (15) | 0.0452 (12) | |
C53 | 0.2297 (5) | 1.0741 (5) | 0.89484 (19) | 0.0655 (17) | |
C54 | 0.2968 (6) | 1.0138 (5) | 0.94080 (18) | 0.0690 (18) | |
C55 | 0.3908 (5) | 0.9154 (5) | 0.93137 (18) | 0.0657 (16) | |
C56 | 0.4188 (5) | 0.8799 (4) | 0.87431 (18) | 0.0601 (17) | |
H1 | 0.28470 | 0.44490 | 0.23870 | 0.0980* | |
H3 | 0.33180 | 0.43850 | 0.09790 | 0.0800* | |
H3A | 0.23170 | 0.57380 | 0.76390 | 0.0920* | |
H4 | 0.22420 | 0.29940 | 0.02180 | 0.0860* | |
H5 | 0.06540 | 0.14300 | 0.03820 | 0.0810* | |
H6 | 0.02060 | 0.12960 | 0.13250 | 0.0690* | |
H8A | 0.04740 | 0.08310 | 0.23130 | 0.0650* | |
H8B | −0.07870 | 0.17910 | 0.22180 | 0.0650* | |
H8C | 0.00500 | 0.17120 | 0.28590 | 0.0650* | |
H10 | −0.05110 | 0.41840 | 0.32310 | 0.0800* | |
H11 | −0.09100 | 0.43330 | 0.41920 | 0.0900* | |
H12 | 0.08850 | 0.38800 | 0.49400 | 0.0900* | |
H14 | 0.34890 | 0.30650 | 0.37530 | 0.0690* | |
H16 | 0.43210 | 0.51760 | 0.54910 | 0.0990* | |
H17 | 0.42620 | 0.57210 | 0.65050 | 0.0890* | |
H19 | 0.23510 | 0.23420 | 0.65530 | 0.0910* | |
H20 | 0.24070 | 0.18310 | 0.55440 | 0.0950* | |
H21A | 0.45930 | 0.20880 | 0.77240 | 0.0690* | |
H21B | 0.58290 | 0.31110 | 0.77870 | 0.0690* | |
H21C | 0.49540 | 0.26590 | 0.71590 | 0.0690* | |
H25 | 0.19110 | 0.64490 | 0.90460 | 0.0780* | |
H26 | 0.28930 | 0.53530 | 0.98150 | 0.0900* | |
H27 | 0.43590 | 0.36410 | 0.96330 | 0.0840* | |
H28 | 0.47910 | 0.30130 | 0.86890 | 0.0640* | |
H4A | 0.27090 | 0.94300 | 0.23620 | 0.0910* | |
H6A | 0.18230 | 1.05890 | 0.76160 | 0.0930* | |
H31 | 0.31150 | 0.94210 | 0.09500 | 0.0780* | |
H32 | 0.20890 | 0.79320 | 0.01760 | 0.0840* | |
H33 | 0.06270 | 0.63300 | 0.03540 | 0.0830* | |
H34 | 0.01880 | 0.61770 | 0.13060 | 0.0680* | |
H36A | 0.00440 | 0.65860 | 0.28360 | 0.0820* | |
H36B | 0.04140 | 0.57340 | 0.22710 | 0.0820* | |
H36C | −0.08200 | 0.67280 | 0.22060 | 0.0820* | |
H38 | 0.07220 | 0.99540 | 0.34970 | 0.0880* | |
H39 | 0.06450 | 0.99080 | 0.45040 | 0.1060* | |
H41 | 0.25940 | 0.65510 | 0.44570 | 0.0940* | |
H42 | 0.26580 | 0.65520 | 0.34470 | 0.0890* | |
H44 | 0.41370 | 0.88820 | 0.50540 | 0.0890* | |
H45 | 0.59070 | 0.97240 | 0.58170 | 0.0810* | |
H46 | 0.54770 | 1.01200 | 0.67700 | 0.0820* | |
H48 | 0.15040 | 0.87220 | 0.62530 | 0.0700* | |
H49A | 0.45300 | 0.71760 | 0.76900 | 0.0630* | |
H49B | 0.57850 | 0.81890 | 0.77860 | 0.0630* | |
H49C | 0.49530 | 0.77850 | 0.71450 | 0.0630* | |
H53 | 0.16520 | 1.13890 | 0.90210 | 0.0790* | |
H54 | 0.27900 | 1.03930 | 0.97930 | 0.0830* | |
H55 | 0.43450 | 0.87380 | 0.96300 | 0.0790* | |
H56 | 0.48280 | 0.81440 | 0.86780 | 0.0720* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.076 (2) | 0.066 (2) | 0.0567 (17) | −0.0137 (16) | 0.0181 (15) | 0.0105 (15) |
O2 | 0.073 (2) | 0.137 (3) | 0.0509 (18) | 0.044 (2) | 0.0093 (15) | 0.0045 (17) |
O3 | 0.074 (2) | 0.0594 (19) | 0.0533 (16) | 0.0192 (15) | 0.0159 (14) | 0.0047 (14) |
N1 | 0.0477 (19) | 0.063 (2) | 0.0402 (18) | −0.0011 (16) | 0.0134 (14) | 0.0087 (16) |
N2 | 0.0468 (19) | 0.058 (2) | 0.0418 (18) | 0.0017 (16) | 0.0076 (14) | −0.0048 (15) |
C1 | 0.050 (2) | 0.049 (2) | 0.037 (2) | 0.0112 (18) | 0.0097 (16) | 0.0118 (17) |
C2 | 0.050 (2) | 0.042 (2) | 0.044 (2) | 0.0002 (18) | 0.0067 (17) | 0.0072 (18) |
C3 | 0.091 (3) | 0.060 (3) | 0.057 (3) | 0.001 (2) | 0.029 (2) | 0.020 (2) |
C4 | 0.096 (4) | 0.089 (4) | 0.034 (2) | 0.011 (3) | 0.020 (2) | 0.010 (2) |
C5 | 0.079 (3) | 0.080 (4) | 0.038 (2) | 0.003 (3) | 0.006 (2) | −0.010 (2) |
C6 | 0.056 (3) | 0.063 (3) | 0.053 (3) | 0.001 (2) | 0.0091 (19) | 0.006 (2) |
C7 | 0.036 (2) | 0.049 (2) | 0.045 (2) | 0.0050 (17) | 0.0073 (16) | 0.0090 (18) |
C8 | 0.057 (3) | 0.057 (3) | 0.052 (2) | −0.004 (2) | 0.0160 (18) | 0.0107 (19) |
C9 | 0.060 (3) | 0.064 (3) | 0.040 (2) | −0.010 (2) | 0.0107 (19) | 0.0100 (19) |
C10 | 0.063 (3) | 0.083 (3) | 0.058 (3) | 0.022 (2) | 0.018 (2) | 0.013 (2) |
C11 | 0.061 (3) | 0.094 (4) | 0.075 (3) | 0.030 (3) | 0.022 (2) | 0.012 (3) |
C12 | 0.076 (3) | 0.097 (4) | 0.048 (3) | 0.001 (3) | 0.017 (2) | −0.015 (2) |
C13 | 0.061 (3) | 0.070 (3) | 0.051 (2) | 0.020 (2) | 0.000 (2) | 0.003 (2) |
C14 | 0.049 (2) | 0.077 (3) | 0.050 (2) | 0.007 (2) | 0.0156 (19) | 0.007 (2) |
C15 | 0.079 (3) | 0.117 (5) | 0.036 (2) | 0.031 (3) | 0.004 (2) | 0.000 (3) |
C16 | 0.081 (4) | 0.109 (5) | 0.066 (3) | −0.009 (3) | 0.024 (3) | 0.028 (3) |
C17 | 0.095 (4) | 0.076 (3) | 0.058 (3) | −0.018 (3) | 0.037 (3) | −0.004 (2) |
C18 | 0.046 (2) | 0.090 (3) | 0.034 (2) | 0.017 (2) | 0.0073 (17) | 0.001 (2) |
C19 | 0.100 (4) | 0.070 (3) | 0.057 (3) | −0.009 (3) | 0.014 (2) | 0.007 (2) |
C20 | 0.106 (4) | 0.074 (3) | 0.053 (3) | 0.004 (3) | 0.006 (3) | −0.009 (2) |
C21 | 0.048 (2) | 0.063 (3) | 0.060 (2) | 0.011 (2) | 0.0120 (19) | 0.002 (2) |
C22 | 0.037 (2) | 0.051 (2) | 0.0359 (19) | −0.0052 (17) | 0.0103 (16) | −0.0036 (17) |
C23 | 0.042 (2) | 0.044 (2) | 0.046 (2) | −0.0057 (17) | 0.0088 (16) | 0.0004 (17) |
C24 | 0.056 (2) | 0.051 (3) | 0.046 (2) | −0.0057 (19) | 0.0133 (18) | 0.0017 (19) |
C25 | 0.089 (3) | 0.062 (3) | 0.047 (2) | 0.003 (2) | 0.026 (2) | −0.006 (2) |
C26 | 0.100 (4) | 0.084 (4) | 0.042 (3) | −0.010 (3) | 0.023 (2) | −0.004 (2) |
C27 | 0.089 (4) | 0.081 (4) | 0.043 (2) | 0.000 (3) | 0.012 (2) | 0.017 (2) |
C28 | 0.056 (3) | 0.063 (3) | 0.041 (2) | −0.001 (2) | 0.0066 (18) | 0.0053 (19) |
O4 | 0.080 (2) | 0.0531 (18) | 0.0496 (16) | −0.0145 (14) | 0.0140 (14) | 0.0046 (13) |
O5 | 0.074 (2) | 0.142 (3) | 0.0492 (18) | −0.036 (2) | 0.0094 (15) | 0.0110 (18) |
O6 | 0.078 (2) | 0.0584 (19) | 0.0506 (16) | 0.0162 (15) | 0.0146 (14) | 0.0058 (13) |
N3 | 0.0473 (19) | 0.065 (2) | 0.0381 (17) | −0.0026 (16) | 0.0063 (14) | 0.0100 (15) |
N4 | 0.0468 (19) | 0.062 (2) | 0.0391 (17) | 0.0058 (16) | 0.0116 (14) | 0.0008 (15) |
C29 | 0.042 (2) | 0.050 (2) | 0.043 (2) | 0.0076 (18) | 0.0064 (16) | 0.0069 (18) |
C30 | 0.059 (3) | 0.055 (3) | 0.041 (2) | 0.012 (2) | 0.0180 (18) | 0.0136 (19) |
C31 | 0.077 (3) | 0.074 (3) | 0.054 (3) | 0.011 (2) | 0.026 (2) | 0.021 (2) |
C32 | 0.094 (4) | 0.076 (4) | 0.046 (3) | 0.011 (3) | 0.024 (2) | 0.006 (2) |
C33 | 0.086 (4) | 0.079 (4) | 0.040 (2) | 0.007 (3) | 0.006 (2) | 0.000 (2) |
C34 | 0.060 (3) | 0.065 (3) | 0.043 (2) | 0.002 (2) | 0.0046 (19) | 0.0021 (19) |
C35 | 0.042 (2) | 0.051 (2) | 0.037 (2) | 0.0112 (18) | 0.0101 (16) | 0.0128 (17) |
C36 | 0.051 (2) | 0.060 (3) | 0.054 (2) | −0.004 (2) | 0.0094 (18) | 0.0114 (19) |
C37 | 0.043 (2) | 0.081 (3) | 0.033 (2) | −0.012 (2) | 0.0042 (16) | 0.0037 (19) |
C38 | 0.096 (4) | 0.079 (3) | 0.055 (3) | 0.032 (3) | 0.031 (2) | 0.024 (2) |
C39 | 0.091 (4) | 0.100 (4) | 0.072 (3) | 0.024 (3) | 0.024 (3) | −0.011 (3) |
C40 | 0.084 (4) | 0.105 (4) | 0.035 (2) | −0.030 (3) | −0.002 (2) | 0.007 (3) |
C41 | 0.097 (4) | 0.082 (4) | 0.056 (3) | 0.002 (3) | 0.006 (3) | 0.018 (2) |
C42 | 0.093 (4) | 0.076 (3) | 0.055 (3) | 0.008 (3) | 0.012 (2) | 0.010 (2) |
C43 | 0.061 (3) | 0.070 (3) | 0.052 (2) | −0.015 (2) | −0.002 (2) | 0.012 (2) |
C44 | 0.071 (3) | 0.106 (4) | 0.051 (3) | 0.017 (3) | 0.017 (2) | 0.024 (3) |
C45 | 0.055 (3) | 0.088 (3) | 0.061 (3) | −0.014 (2) | 0.016 (2) | 0.006 (2) |
C46 | 0.066 (3) | 0.081 (3) | 0.061 (3) | −0.012 (2) | 0.020 (2) | 0.004 (2) |
C47 | 0.061 (3) | 0.059 (3) | 0.038 (2) | 0.016 (2) | 0.0049 (19) | −0.0011 (18) |
C48 | 0.052 (2) | 0.077 (3) | 0.049 (2) | 0.003 (2) | 0.0176 (19) | 0.008 (2) |
C49 | 0.056 (2) | 0.051 (2) | 0.050 (2) | 0.0047 (19) | 0.0118 (18) | 0.0021 (18) |
C50 | 0.042 (2) | 0.042 (2) | 0.044 (2) | −0.0007 (17) | 0.0032 (17) | 0.0004 (17) |
C51 | 0.048 (2) | 0.049 (2) | 0.040 (2) | −0.0036 (18) | 0.0094 (17) | −0.0005 (17) |
C52 | 0.054 (2) | 0.042 (2) | 0.039 (2) | −0.0026 (18) | 0.0087 (17) | 0.0002 (17) |
C53 | 0.082 (3) | 0.059 (3) | 0.058 (3) | 0.000 (2) | 0.025 (2) | −0.001 (2) |
C54 | 0.096 (4) | 0.073 (3) | 0.040 (2) | −0.010 (3) | 0.025 (2) | −0.004 (2) |
C55 | 0.084 (3) | 0.077 (3) | 0.035 (2) | −0.008 (3) | 0.006 (2) | 0.006 (2) |
C56 | 0.063 (3) | 0.065 (3) | 0.052 (3) | 0.006 (2) | 0.005 (2) | 0.011 (2) |
Geometric parameters (Å, º) top
O1—C2 | 1.345 (5) | C17—H17 | 0.9300 |
O2—C13 | 1.390 (6) | C19—H19 | 0.9300 |
O2—C15 | 1.393 (5) | C20—H20 | 0.9300 |
O3—C24 | 1.349 (5) | C21—H21C | 0.9600 |
O1—H1 | 0.8200 | C21—H21B | 0.9600 |
O3—H3A | 0.8200 | C21—H21A | 0.9600 |
O4—C30 | 1.360 (5) | C25—H25 | 0.9300 |
O5—C40 | 1.407 (5) | C26—H26 | 0.9300 |
O5—C43 | 1.396 (6) | C27—H27 | 0.9300 |
O6—C52 | 1.347 (5) | C28—H28 | 0.9300 |
O4—H4A | 0.8200 | C29—C34 | 1.397 (6) |
O6—H6A | 0.8200 | C29—C35 | 1.491 (5) |
N1—C7 | 1.291 (5) | C29—C30 | 1.380 (6) |
N1—C9 | 1.426 (5) | C30—C31 | 1.403 (6) |
N2—C18 | 1.405 (5) | C31—C32 | 1.383 (7) |
N2—C22 | 1.295 (5) | C32—C33 | 1.360 (8) |
N3—C37 | 1.412 (5) | C33—C34 | 1.381 (6) |
N3—C35 | 1.293 (5) | C35—C36 | 1.478 (6) |
N4—C50 | 1.288 (5) | C37—C42 | 1.451 (7) |
N4—C47 | 1.427 (5) | C37—C38 | 1.324 (6) |
C1—C7 | 1.455 (5) | C38—C39 | 1.402 (6) |
C1—C2 | 1.431 (6) | C39—C40 | 1.315 (8) |
C1—C6 | 1.396 (6) | C40—C41 | 1.391 (8) |
C2—C3 | 1.384 (6) | C41—C42 | 1.376 (6) |
C3—C4 | 1.337 (7) | C43—C44 | 1.371 (7) |
C4—C5 | 1.393 (7) | C43—C48 | 1.371 (6) |
C5—C6 | 1.363 (6) | C44—C45 | 1.389 (7) |
C7—C8 | 1.498 (6) | C45—C46 | 1.344 (6) |
C9—C14 | 1.353 (6) | C46—C47 | 1.446 (7) |
C9—C10 | 1.444 (7) | C47—C48 | 1.337 (6) |
C10—C11 | 1.344 (6) | C49—C50 | 1.507 (6) |
C11—C12 | 1.385 (7) | C50—C51 | 1.471 (5) |
C12—C13 | 1.350 (7) | C51—C56 | 1.405 (6) |
C13—C14 | 1.368 (6) | C51—C52 | 1.405 (6) |
C15—C16 | 1.310 (8) | C52—C53 | 1.392 (6) |
C15—C20 | 1.404 (8) | C53—C54 | 1.362 (7) |
C16—C17 | 1.416 (6) | C54—C55 | 1.382 (7) |
C17—C18 | 1.324 (7) | C55—C56 | 1.380 (6) |
C18—C19 | 1.440 (7) | C31—H31 | 0.9300 |
C19—C20 | 1.378 (6) | C32—H32 | 0.9300 |
C21—C22 | 1.489 (6) | C33—H33 | 0.9300 |
C22—C23 | 1.471 (5) | C34—H34 | 0.9300 |
C23—C28 | 1.385 (5) | C36—H36A | 0.9600 |
C23—C24 | 1.409 (6) | C36—H36B | 0.9600 |
C24—C25 | 1.378 (6) | C36—H36C | 0.9600 |
C25—C26 | 1.363 (7) | C38—H38 | 0.9300 |
C26—C27 | 1.373 (8) | C39—H39 | 0.9300 |
C27—C28 | 1.368 (6) | C41—H41 | 0.9300 |
C3—H3 | 0.9300 | C42—H42 | 0.9300 |
C4—H4 | 0.9300 | C44—H44 | 0.9300 |
C5—H5 | 0.9300 | C45—H45 | 0.9300 |
C6—H6 | 0.9300 | C46—H46 | 0.9300 |
C8—H8C | 0.9600 | C48—H48 | 0.9300 |
C8—H8A | 0.9600 | C49—H49A | 0.9600 |
C8—H8B | 0.9600 | C49—H49B | 0.9600 |
C10—H10 | 0.9300 | C49—H49C | 0.9600 |
C11—H11 | 0.9300 | C53—H53 | 0.9300 |
C12—H12 | 0.9300 | C54—H54 | 0.9300 |
C14—H14 | 0.9300 | C55—H55 | 0.9300 |
C16—H16 | 0.9300 | C56—H56 | 0.9300 |
| | | |
O1···N1 | 2.546 (4) | C40···H44 | 2.5400 |
O1···C49i | 3.379 (5) | C41···H44 | 2.8100 |
O1···C21i | 3.254 (5) | C42···H36A | 2.6300 |
O1···C22i | 3.235 (5) | C46···H49C | 2.6700 |
O2···C44i | 3.400 (6) | C47···H49C | 2.4300 |
O3···N2 | 2.531 (4) | C49···H56 | 2.5500 |
O3···C36ii | 3.383 (5) | C50···H46 | 3.0600 |
O3···C8ii | 3.313 (5) | C50···H8Bii | 3.0800 |
O3···C7ii | 3.365 (5) | C50···H6A | 2.5200 |
O4···C50iii | 3.362 (5) | C51···H8Bii | 2.8900 |
O4···N3 | 2.536 (4) | C52···H8Bii | 2.9200 |
O4···C21i | 3.366 (5) | C56···H49A | 2.8400 |
O4···C49iii | 3.301 (5) | C56···H49B | 2.8600 |
O6···C8ii | 3.377 (5) | H1···C9 | 3.0000 |
O6···C36iv | 3.241 (5) | H1···C7 | 2.4400 |
O6···C35iv | 3.227 (5) | H1···N1 | 1.8200 |
O6···N4 | 2.556 (4) | H3···C28i | 3.0300 |
O1···H36B | 2.8900 | H3A···H10ii | 2.4300 |
O1···H21Bi | 2.5900 | H3A···C18 | 2.9700 |
O3···H10ii | 2.8800 | H3A···N2 | 1.8000 |
O3···H49A | 2.7800 | H3A···C22 | 2.4300 |
O3···H8Bii | 2.6300 | H3A···H49A | 2.5600 |
O4···H46iii | 2.8900 | H4A···C35 | 2.4500 |
O4···H8Av | 2.7900 | H4A···N3 | 1.8100 |
O4···H49Biii | 2.6100 | H4A···H46iii | 2.4200 |
O6···H21Av | 2.9100 | H4A···C37 | 2.9800 |
O6···H36Civ | 2.5800 | H4A···H8Av | 2.5700 |
N1···O1 | 2.546 (4) | H6···C8 | 2.5500 |
N2···O3 | 2.531 (4) | H6···H8A | 2.3400 |
N3···O4 | 2.536 (4) | H6···H8B | 2.3800 |
N4···O6 | 2.556 (4) | H6A···C8ii | 2.9800 |
N1···H1 | 1.8200 | H6A···N4 | 1.9300 |
N2···H3A | 1.8000 | H6A···C50 | 2.5200 |
N3···H4A | 1.8100 | H8A···O4vi | 2.7900 |
N4···H6A | 1.9300 | H8A···H6 | 2.3400 |
C2···C49i | 3.513 (6) | H8A···C6 | 2.8400 |
C7···O3ii | 3.365 (5) | H8A···H4Avi | 2.5700 |
C8···C52ii | 3.508 (6) | H8B···C50ii | 3.0800 |
C8···C10 | 3.247 (6) | H8B···C6 | 2.8700 |
C8···O6ii | 3.377 (5) | H8B···H6 | 2.3800 |
C8···O3ii | 3.313 (5) | H8B···O3ii | 2.6300 |
C10···C8 | 3.247 (6) | H8B···C51ii | 2.8900 |
C12···C16 | 3.525 (7) | H8B···C52ii | 2.9200 |
C12···C20 | 3.337 (7) | H8C···C9 | 2.4400 |
C16···C12 | 3.525 (7) | H8C···H38vi | 2.5000 |
C19···C21 | 3.231 (6) | H8C···C10 | 2.6500 |
C20···C12 | 3.337 (7) | H10···H3Aii | 2.4300 |
C21···O1i | 3.254 (5) | H10···C7 | 3.0400 |
C21···C30i | 3.513 (6) | H10···O3ii | 2.8800 |
C21···O4i | 3.366 (5) | H11···C17ii | 3.0300 |
C21···C19 | 3.231 (6) | H11···H12ii | 2.5600 |
C22···O1i | 3.235 (5) | H12···C20 | 2.8100 |
C24···C36ii | 3.524 (6) | H12···C15 | 2.5300 |
C30···C21i | 3.513 (6) | H12···C11ii | 3.0900 |
C35···O6iv | 3.227 (5) | H12···H11ii | 2.5600 |
C36···C24ii | 3.524 (6) | H17···H49C | 2.4900 |
C36···O6iv | 3.241 (5) | H19···C21 | 3.1000 |
C36···C42 | 3.238 (6) | H19···C22 | 3.0200 |
C36···O3ii | 3.383 (5) | H21A···O6vi | 2.9100 |
C39···C44 | 3.542 (7) | H21A···C28 | 2.8100 |
C41···C44 | 3.328 (7) | H21A···H28 | 2.2900 |
C42···C36 | 3.238 (6) | H21B···O1i | 2.5900 |
C44···C39 | 3.542 (7) | H21B···C29i | 2.8600 |
C44···C41 | 3.328 (7) | H21B···C28 | 2.9000 |
C44···O2i | 3.400 (6) | H21B···H28 | 2.4300 |
C46···C49 | 3.258 (6) | H21B···C30i | 2.9100 |
C49···C46 | 3.258 (6) | H21B···C35i | 3.0200 |
C49···C2i | 3.513 (6) | H21C···C18 | 2.4500 |
C49···O4iii | 3.301 (5) | H21C···C19 | 2.6200 |
C49···O1i | 3.379 (5) | H28···H21B | 2.4300 |
C50···O4iii | 3.362 (5) | H28···C21 | 2.5500 |
C52···C8ii | 3.508 (6) | H28···H21A | 2.2900 |
C1···H49Bi | 2.8900 | H34···C36 | 2.5400 |
C2···H49Bi | 2.9300 | H34···H36B | 2.2800 |
C6···H8B | 2.8700 | H34···H36C | 2.4100 |
C6···H8A | 2.8400 | H36A···C37 | 2.4500 |
C7···H49Bi | 3.0900 | H36A···C42 | 2.6300 |
C7···H10 | 3.0400 | H36B···O1 | 2.8900 |
C7···H1 | 2.4400 | H36B···C34 | 2.8100 |
C8···H6Aii | 2.9800 | H36B···H34 | 2.2800 |
C8···H6 | 2.5500 | H36C···C34 | 2.8800 |
C9···H1 | 3.0000 | H36C···H34 | 2.4100 |
C9···H8C | 2.4400 | H36C···O6iv | 2.5800 |
C10···H8C | 2.6500 | H36C···C22ii | 3.0300 |
C11···H12ii | 3.0900 | H36C···C23ii | 2.8800 |
C15···H12 | 2.5300 | H36C···C24ii | 2.9300 |
C17···H11ii | 3.0300 | H38···H8Cv | 2.5000 |
C18···H3A | 2.9700 | H42···C35 | 3.0300 |
C18···H21C | 2.4500 | H44···C40 | 2.5400 |
C19···H21C | 2.6200 | H44···C41 | 2.8100 |
C20···H12 | 2.8100 | H44···H45iii | 2.6000 |
C21···H19 | 3.1000 | H45···C38iii | 3.0400 |
C21···H28 | 2.5500 | H45···H44iii | 2.6000 |
C22···H19 | 3.0200 | H46···C50 | 3.0600 |
C22···H36Cii | 3.0300 | H46···O4iii | 2.8900 |
C22···H3A | 2.4300 | H46···H4Aiii | 2.4200 |
C23···H36Cii | 2.8800 | H49A···O3 | 2.7800 |
C24···H36Cii | 2.9300 | H49A···C56 | 2.8400 |
C28···H21A | 2.8100 | H49A···H3A | 2.5600 |
C28···H21B | 2.9000 | H49A···H56 | 2.3400 |
C28···H3i | 3.0300 | H49B···C56 | 2.8600 |
C29···H21Bi | 2.8600 | H49B···H56 | 2.3600 |
C30···H21Bi | 2.9100 | H49B···O4iii | 2.6100 |
C34···H36B | 2.8100 | H49B···C1i | 2.8900 |
C34···H53iv | 3.0000 | H49B···C2i | 2.9300 |
C34···H36C | 2.8800 | H49B···C7i | 3.0900 |
C35···H42 | 3.0300 | H49C···C46 | 2.6700 |
C35···H21Bi | 3.0200 | H49C···C47 | 2.4300 |
C35···H4A | 2.4500 | H49C···H17 | 2.4900 |
C36···H34 | 2.5400 | H53···C34iv | 3.0000 |
C37···H4A | 2.9800 | H56···C49 | 2.5500 |
C37···H36A | 2.4500 | H56···H49A | 2.3400 |
C38···H45iii | 3.0400 | H56···H49B | 2.3600 |
| | | |
C13—O2—C15 | 118.5 (4) | C27—C26—H26 | 120.00 |
C2—O1—H1 | 109.00 | C28—C27—H27 | 120.00 |
C24—O3—H3A | 109.00 | C26—C27—H27 | 120.00 |
C40—O5—C43 | 118.9 (4) | C27—C28—H28 | 119.00 |
C30—O4—H4A | 109.00 | C23—C28—H28 | 119.00 |
C52—O6—H6A | 109.00 | C34—C29—C35 | 120.3 (4) |
C7—N1—C9 | 122.8 (3) | C30—C29—C35 | 121.7 (3) |
C18—N2—C22 | 122.7 (3) | C30—C29—C34 | 118.0 (3) |
C35—N3—C37 | 122.1 (3) | O4—C30—C31 | 116.7 (4) |
C47—N4—C50 | 122.6 (3) | O4—C30—C29 | 122.8 (3) |
C2—C1—C6 | 116.1 (3) | C29—C30—C31 | 120.5 (4) |
C2—C1—C7 | 122.0 (3) | C30—C31—C32 | 119.7 (4) |
C6—C1—C7 | 122.0 (4) | C31—C32—C33 | 120.3 (4) |
C1—C2—C3 | 119.9 (4) | C32—C33—C34 | 120.1 (4) |
O1—C2—C3 | 119.1 (4) | C29—C34—C33 | 121.4 (4) |
O1—C2—C1 | 121.0 (3) | N3—C35—C36 | 124.5 (3) |
C2—C3—C4 | 121.5 (5) | N3—C35—C29 | 116.6 (3) |
C3—C4—C5 | 120.7 (4) | C29—C35—C36 | 118.9 (3) |
C4—C5—C6 | 118.9 (4) | N3—C37—C42 | 119.3 (4) |
C1—C6—C5 | 123.0 (4) | N3—C37—C38 | 122.2 (4) |
C1—C7—C8 | 118.9 (3) | C38—C37—C42 | 118.3 (4) |
N1—C7—C8 | 123.2 (3) | C37—C38—C39 | 121.8 (5) |
N1—C7—C1 | 117.9 (4) | C38—C39—C40 | 119.9 (5) |
N1—C9—C10 | 119.4 (4) | O5—C40—C41 | 119.6 (5) |
C10—C9—C14 | 117.7 (4) | C39—C40—C41 | 122.0 (4) |
N1—C9—C14 | 122.3 (4) | O5—C40—C39 | 118.3 (5) |
C9—C10—C11 | 119.7 (4) | C40—C41—C42 | 118.8 (5) |
C10—C11—C12 | 120.6 (5) | C37—C42—C41 | 119.2 (5) |
C11—C12—C13 | 119.7 (4) | O5—C43—C44 | 122.6 (4) |
C12—C13—C14 | 121.0 (4) | C44—C43—C48 | 121.8 (4) |
O2—C13—C14 | 115.3 (4) | O5—C43—C48 | 115.6 (4) |
O2—C13—C12 | 123.7 (4) | C43—C44—C45 | 117.3 (4) |
C9—C14—C13 | 121.3 (4) | C44—C45—C46 | 122.0 (5) |
O2—C15—C20 | 118.2 (5) | C45—C46—C47 | 119.2 (4) |
O2—C15—C16 | 120.6 (5) | N4—C47—C48 | 122.3 (4) |
C16—C15—C20 | 121.1 (4) | N4—C47—C46 | 118.8 (4) |
C15—C16—C17 | 120.5 (5) | C46—C47—C48 | 117.8 (4) |
C16—C17—C18 | 121.3 (5) | C43—C48—C47 | 121.4 (4) |
N2—C18—C17 | 121.7 (4) | N4—C50—C51 | 118.5 (4) |
N2—C18—C19 | 119.6 (4) | C49—C50—C51 | 118.7 (3) |
C17—C18—C19 | 118.5 (4) | N4—C50—C49 | 122.9 (3) |
C18—C19—C20 | 119.6 (5) | C52—C51—C56 | 117.9 (3) |
C15—C20—C19 | 118.9 (5) | C50—C51—C52 | 121.2 (3) |
N2—C22—C21 | 123.7 (3) | C50—C51—C56 | 120.9 (4) |
C21—C22—C23 | 119.0 (3) | C51—C52—C53 | 119.9 (4) |
N2—C22—C23 | 117.3 (4) | O6—C52—C51 | 122.4 (3) |
C22—C23—C28 | 121.3 (4) | O6—C52—C53 | 117.7 (4) |
C22—C23—C24 | 121.9 (3) | C52—C53—C54 | 120.5 (4) |
C24—C23—C28 | 116.8 (3) | C53—C54—C55 | 121.3 (4) |
O3—C24—C23 | 121.3 (3) | C54—C55—C56 | 119.0 (4) |
O3—C24—C25 | 118.5 (4) | C51—C56—C55 | 121.5 (4) |
C23—C24—C25 | 120.2 (4) | C30—C31—H31 | 120.00 |
C24—C25—C26 | 121.3 (5) | C32—C31—H31 | 120.00 |
C25—C26—C27 | 119.3 (4) | C31—C32—H32 | 120.00 |
C26—C27—C28 | 120.2 (4) | C33—C32—H32 | 120.00 |
C23—C28—C27 | 122.1 (4) | C32—C33—H33 | 120.00 |
C4—C3—H3 | 119.00 | C34—C33—H33 | 120.00 |
C2—C3—H3 | 119.00 | C29—C34—H34 | 119.00 |
C3—C4—H4 | 120.00 | C33—C34—H34 | 119.00 |
C5—C4—H4 | 120.00 | C35—C36—H36A | 109.00 |
C6—C5—H5 | 121.00 | C35—C36—H36B | 109.00 |
C4—C5—H5 | 121.00 | C35—C36—H36C | 109.00 |
C5—C6—H6 | 118.00 | H36A—C36—H36B | 110.00 |
C1—C6—H6 | 119.00 | H36A—C36—H36C | 109.00 |
H8A—C8—H8C | 110.00 | H36B—C36—H36C | 109.00 |
H8A—C8—H8B | 109.00 | C37—C38—H38 | 119.00 |
C7—C8—H8A | 109.00 | C39—C38—H38 | 119.00 |
C7—C8—H8C | 109.00 | C38—C39—H39 | 120.00 |
C7—C8—H8B | 109.00 | C40—C39—H39 | 120.00 |
H8B—C8—H8C | 109.00 | C40—C41—H41 | 121.00 |
C9—C10—H10 | 120.00 | C42—C41—H41 | 121.00 |
C11—C10—H10 | 120.00 | C37—C42—H42 | 120.00 |
C10—C11—H11 | 120.00 | C41—C42—H42 | 120.00 |
C12—C11—H11 | 120.00 | C43—C44—H44 | 121.00 |
C13—C12—H12 | 120.00 | C45—C44—H44 | 121.00 |
C11—C12—H12 | 120.00 | C44—C45—H45 | 119.00 |
C9—C14—H14 | 119.00 | C46—C45—H45 | 119.00 |
C13—C14—H14 | 119.00 | C45—C46—H46 | 120.00 |
C15—C16—H16 | 120.00 | C47—C46—H46 | 120.00 |
C17—C16—H16 | 120.00 | C43—C48—H48 | 119.00 |
C18—C17—H17 | 119.00 | C47—C48—H48 | 119.00 |
C16—C17—H17 | 119.00 | C50—C49—H49A | 109.00 |
C20—C19—H19 | 120.00 | C50—C49—H49B | 110.00 |
C18—C19—H19 | 120.00 | C50—C49—H49C | 110.00 |
C15—C20—H20 | 121.00 | H49A—C49—H49B | 110.00 |
C19—C20—H20 | 120.00 | H49A—C49—H49C | 109.00 |
H21A—C21—H21B | 110.00 | H49B—C49—H49C | 109.00 |
C22—C21—H21C | 109.00 | C52—C53—H53 | 120.00 |
H21A—C21—H21C | 109.00 | C54—C53—H53 | 120.00 |
H21B—C21—H21C | 109.00 | C53—C54—H54 | 119.00 |
C22—C21—H21A | 109.00 | C55—C54—H54 | 119.00 |
C22—C21—H21B | 109.00 | C54—C55—H55 | 120.00 |
C24—C25—H25 | 119.00 | C56—C55—H55 | 121.00 |
C26—C25—H25 | 119.00 | C51—C56—H56 | 119.00 |
C25—C26—H26 | 120.00 | C55—C56—H56 | 119.00 |
| | | |
C13—O2—C15—C16 | −92.8 (6) | N2—C22—C23—C24 | −2.5 (6) |
C13—O2—C15—C20 | 89.2 (6) | C28—C23—C24—O3 | −179.5 (4) |
C15—O2—C13—C12 | −12.9 (7) | C28—C23—C24—C25 | 0.5 (6) |
C15—O2—C13—C14 | 167.9 (4) | C22—C23—C24—C25 | 179.0 (4) |
C43—O5—C40—C41 | 86.5 (6) | C24—C23—C28—C27 | 0.0 (6) |
C40—O5—C43—C48 | 169.1 (4) | C22—C23—C28—C27 | −178.5 (4) |
C43—O5—C40—C39 | −96.4 (6) | C22—C23—C24—O3 | −1.0 (6) |
C40—O5—C43—C44 | −9.3 (7) | O3—C24—C25—C26 | 178.9 (4) |
C7—N1—C9—C14 | 120.6 (5) | C23—C24—C25—C26 | −1.0 (7) |
C9—N1—C7—C8 | −5.1 (6) | C24—C25—C26—C27 | 1.1 (8) |
C9—N1—C7—C1 | 177.0 (4) | C25—C26—C27—C28 | −0.6 (8) |
C7—N1—C9—C10 | −68.3 (5) | C26—C27—C28—C23 | 0.1 (8) |
C18—N2—C22—C23 | −178.0 (4) | C30—C29—C35—N3 | −3.0 (6) |
C18—N2—C22—C21 | 4.0 (6) | C34—C29—C35—C36 | −5.2 (6) |
C22—N2—C18—C19 | 68.1 (5) | C30—C29—C34—C33 | 0.8 (7) |
C22—N2—C18—C17 | −117.2 (5) | C34—C29—C35—N3 | 176.5 (4) |
C35—N3—C37—C42 | 68.7 (5) | C35—C29—C34—C33 | −178.7 (4) |
C35—N3—C37—C38 | −116.3 (5) | C30—C29—C35—C36 | 175.3 (4) |
C37—N3—C35—C29 | −178.2 (3) | C35—C29—C30—C31 | 178.9 (4) |
C37—N3—C35—C36 | 3.6 (6) | C34—C29—C30—C31 | −0.6 (6) |
C50—N4—C47—C48 | 121.9 (5) | C34—C29—C30—O4 | 180.0 (4) |
C50—N4—C47—C46 | −70.8 (5) | C35—C29—C30—O4 | −0.5 (6) |
C47—N4—C50—C49 | −4.1 (6) | C29—C30—C31—C32 | −0.1 (7) |
C47—N4—C50—C51 | 177.3 (4) | O4—C30—C31—C32 | 179.4 (4) |
C6—C1—C7—N1 | 177.8 (4) | C30—C31—C32—C33 | 0.6 (8) |
C2—C1—C7—C8 | 179.8 (4) | C31—C32—C33—C34 | −0.4 (8) |
C2—C1—C7—N1 | −2.2 (6) | C32—C33—C34—C29 | −0.3 (8) |
C6—C1—C2—C3 | −0.1 (6) | C38—C37—C42—C41 | 0.0 (7) |
C7—C1—C2—O1 | 0.3 (6) | N3—C37—C42—C41 | 175.1 (4) |
C7—C1—C6—C5 | 179.6 (4) | N3—C37—C38—C39 | −175.4 (5) |
C2—C1—C6—C5 | −0.4 (6) | C42—C37—C38—C39 | −0.4 (8) |
C7—C1—C2—C3 | 179.9 (4) | C37—C38—C39—C40 | 1.0 (9) |
C6—C1—C7—C8 | −0.2 (6) | C38—C39—C40—C41 | −1.0 (9) |
C6—C1—C2—O1 | −179.8 (4) | C38—C39—C40—O5 | −178.1 (5) |
O1—C2—C3—C4 | −180.0 (5) | C39—C40—C41—C42 | 0.5 (9) |
C1—C2—C3—C4 | 0.4 (7) | O5—C40—C41—C42 | 177.6 (5) |
C2—C3—C4—C5 | −0.2 (8) | C40—C41—C42—C37 | 0.0 (8) |
C3—C4—C5—C6 | −0.4 (8) | O5—C43—C44—C45 | 177.3 (4) |
C4—C5—C6—C1 | 0.7 (7) | C44—C43—C48—C47 | −3.2 (7) |
C10—C9—C14—C13 | 4.2 (6) | C48—C43—C44—C45 | −1.0 (7) |
N1—C9—C14—C13 | 175.4 (4) | O5—C43—C48—C47 | 178.5 (4) |
N1—C9—C10—C11 | −176.4 (4) | C43—C44—C45—C46 | −0.2 (8) |
C14—C9—C10—C11 | −4.9 (7) | C44—C45—C46—C47 | 5.1 (8) |
C9—C10—C11—C12 | 2.8 (8) | C45—C46—C47—C48 | −8.9 (7) |
C10—C11—C12—C13 | 0.2 (8) | C45—C46—C47—N4 | −176.8 (4) |
C11—C12—C13—O2 | 179.8 (5) | C46—C47—C48—C43 | 7.9 (7) |
C11—C12—C13—C14 | −1.0 (7) | N4—C47—C48—C43 | 175.4 (4) |
O2—C13—C14—C9 | 178.0 (4) | N4—C50—C51—C52 | −1.4 (6) |
C12—C13—C14—C9 | −1.3 (7) | N4—C50—C51—C56 | 178.5 (4) |
O2—C15—C16—C17 | −177.6 (5) | C49—C50—C51—C52 | 180.0 (4) |
C16—C15—C20—C19 | −0.5 (9) | C49—C50—C51—C56 | −0.2 (6) |
C20—C15—C16—C17 | 0.3 (9) | C50—C51—C52—O6 | −0.8 (6) |
O2—C15—C20—C19 | 177.5 (5) | C50—C51—C52—C53 | 179.5 (4) |
C15—C16—C17—C18 | 0.4 (9) | C56—C51—C52—O6 | 179.3 (4) |
C16—C17—C18—C19 | −0.8 (8) | C56—C51—C52—C53 | −0.3 (6) |
C16—C17—C18—N2 | −175.5 (5) | C50—C51—C56—C55 | −179.7 (4) |
N2—C18—C19—C20 | 175.4 (4) | C52—C51—C56—C55 | 0.2 (6) |
C17—C18—C19—C20 | 0.5 (8) | O6—C52—C53—C54 | −178.7 (4) |
C18—C19—C20—C15 | 0.1 (8) | C51—C52—C53—C54 | 1.0 (7) |
C21—C22—C23—C24 | 175.6 (4) | C52—C53—C54—C55 | −1.5 (8) |
N2—C22—C23—C28 | 175.9 (4) | C53—C54—C55—C56 | 1.3 (8) |
C21—C22—C23—C28 | −6.0 (6) | C54—C55—C56—C51 | −0.7 (7) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+2, −z+1; (iv) −x, −y+2, −z+1; (v) x, y+1, z; (vi) x, y−1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 1.82 | 2.546 (4) | 148 |
O3—H3A···N2 | 0.82 | 1.80 | 2.531 (4) | 148 |
O4—H4A···N3 | 0.82 | 1.81 | 2.536 (4) | 146 |
O6—H6A···N4 | 0.82 | 1.93 | 2.556 (4) | 133 |
C8—H8B···O3ii | 0.96 (1) | 2.63 (1) | 3.313 (5) | 129 |
C21—H21B···O1i | 0.96 | 2.59 | 3.254 (5) | 126 |
C36—H36C···O6iv | 0.96 | 2.58 | 3.241 (5) | 126 |
C49—H49B···O4iii | 0.96 (1) | 2.61 (1) | 3.301 (5) | 129 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+2, −z+1; (iv) −x, −y+2, −z+1. |